The crystal structure of α-glycine has been investigated in the temperature range 288–427 K using neutron diffraction. The molecular structure does not change significantly and the putative crystallographic phase transition associated with anomalous electrical behaviour in this temperature range is not observed. The unit cell expands anisotropically with increasing temperature, with the unique monoclinic b axis, corresponding to the stacking direction of molecular layers, changing the most. The increasing separation of antiferroelectric molecular layers with increasing temperature is driven by an increase in molecular libration about an axis that lies perpendicular to the b axis. There is also a weakening of the interlayer hydrogen bonds with temperature. These structural and dynamic changes will affect the response of molecular dipoles to an applied electric field and provide a possible mechanism for the anomalous electrical behaviour.
Supporting information
CCDC references: 193596; 193597; 193598; 193599; 193600; 193601
For all compounds, data collection: ILL MAD; cell refinement: ILL RAFD9. Data reduction: ILL RETREAT for 288K, 301K, 304K, 313K, 427K; ILL RAFD9 for 323K. For all compounds, program(s) used to solve structure: SHELXL97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON.
Crystal data top
C8H20N4O8 | F(000) = 62 |
Mr = 300.24 | Dx = 1.615 Mg m−3 |
Monoclinic, P21/n | Neutron radiation, λ = 0.83950 Å |
a = 5.0993 (3) Å | Cell parameters from 1319 reflections |
b = 11.9416 (6) Å | θ = 4.0–45.0° |
c = 5.4608 (3) Å | µ = 0.24 mm−1 |
β = 111.784 (2)° | T = 288 K |
V = 308.78 (3) Å3 | Needle, none |
Z = 1 | 6 × 1.8 × 1.7 mm |
Data collection top
D9 diffractometer | Rint = 0.016 |
Radiation source: ILL reactor | θmax = 45.0°, θmin = 4.0° |
equatorial geometry scans | h = −8→2 |
Absorption correction: gaussian P. Coppens: The evaluation of absorption and extinction in
single crystal structure analysis in crystallographic computing,
ed F.R.Ahmed, Munsgaad, 1970. | k = −13→18 |
Tmin = 0.550, Tmax = 0.706 | l = −6→9 |
1540 measured reflections | 3 standard reflections every 50 reflections |
1319 independent reflections | intensity decay: none |
1249 reflections with I > 2σ(I) | |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.037 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.078 | w = 1/[σ2(Fo2) + (0.0324P)2 + 0.5346P] where P = (Fo2 + 2Fc2)/3 |
S = 1.20 | (Δ/σ)max < 0.001 |
1319 reflections | Δρmax = 0.68 e Å−3 |
92 parameters | Δρmin = −0.62 e Å−3 |
0 restraints | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.615 (18) |
Crystal data top
C8H20N4O8 | V = 308.78 (3) Å3 |
Mr = 300.24 | Z = 1 |
Monoclinic, P21/n | Neutron radiation, λ = 0.83950 Å |
a = 5.0993 (3) Å | µ = 0.24 mm−1 |
b = 11.9416 (6) Å | T = 288 K |
c = 5.4608 (3) Å | 6 × 1.8 × 1.7 mm |
β = 111.784 (2)° | |
Data collection top
D9 diffractometer | 1249 reflections with I > 2σ(I) |
Absorption correction: gaussian P. Coppens: The evaluation of absorption and extinction in
single crystal structure analysis in crystallographic computing,
ed F.R.Ahmed, Munsgaad, 1970. | Rint = 0.016 |
Tmin = 0.550, Tmax = 0.706 | 3 standard reflections every 50 reflections |
1540 measured reflections | intensity decay: none |
1319 independent reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.037 | 0 restraints |
wR(F2) = 0.078 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.20 | Δρmax = 0.68 e Å−3 |
1319 reflections | Δρmin = −0.62 e Å−3 |
92 parameters | |
Special details top
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F2, conventional
R-factors R are based on F, with F set to zero for
negative F2. The threshold expression of F2 >
σ(F2) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F2 are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O1 | 0.30477 (17) | 0.09419 (8) | 0.23523 (15) | 0.02178 (18) | |
O2 | −0.14853 (18) | 0.14157 (9) | 0.10710 (18) | 0.02504 (19) | |
N3 | 0.30030 (10) | 0.08977 (5) | −0.25894 (9) | 0.01858 (13) | |
C4 | 0.07438 (12) | 0.12480 (5) | 0.06593 (12) | 0.01364 (13) | |
C5 | 0.06373 (13) | 0.14504 (6) | −0.21334 (12) | 0.01592 (14) | |
H6 | 0.2883 (4) | 0.10017 (18) | −0.4544 (3) | 0.0325 (3) | |
H7 | 0.4949 (4) | 0.1191 (2) | −0.1310 (4) | 0.0360 (4) | |
H8 | 0.2977 (5) | 0.00465 (16) | −0.2260 (4) | 0.0382 (4) | |
H9 | 0.0767 (5) | 0.23489 (16) | −0.2434 (4) | 0.0407 (4) | |
H10 | −0.1343 (4) | 0.1145 (2) | −0.3568 (4) | 0.0419 (4) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0199 (3) | 0.0343 (4) | 0.0128 (3) | 0.0060 (3) | 0.0079 (3) | 0.0036 (3) |
O2 | 0.0185 (3) | 0.0402 (5) | 0.0211 (4) | 0.0016 (3) | 0.0127 (3) | −0.0027 (3) |
N3 | 0.0192 (2) | 0.0271 (2) | 0.0116 (2) | 0.00508 (15) | 0.00822 (15) | 0.00170 (15) |
C4 | 0.0152 (2) | 0.0158 (3) | 0.0124 (2) | −0.00079 (17) | 0.00792 (19) | −0.00083 (18) |
C5 | 0.0163 (2) | 0.0199 (3) | 0.0128 (3) | 0.00294 (19) | 0.00693 (19) | 0.0033 (2) |
H6 | 0.0334 (7) | 0.0480 (9) | 0.0202 (6) | 0.0048 (6) | 0.0149 (5) | 0.0035 (6) |
H7 | 0.0247 (6) | 0.0566 (11) | 0.0266 (7) | 0.0010 (6) | 0.0095 (5) | −0.0015 (7) |
H8 | 0.0526 (11) | 0.0309 (8) | 0.0314 (8) | 0.0128 (7) | 0.0159 (8) | 0.0027 (6) |
H9 | 0.0604 (12) | 0.0263 (7) | 0.0446 (10) | 0.0116 (7) | 0.0302 (9) | 0.0139 (7) |
H10 | 0.0241 (7) | 0.0730 (14) | 0.0251 (7) | −0.0014 (8) | 0.0049 (6) | −0.0061 (8) |
Geometric parameters (Å, º) top
O1—C4 | 1.2500 (10) | N3—H8 | 1.033 (2) |
O2—C4 | 1.2540 (9) | C4—C5 | 1.5250 (9) |
N3—C5 | 1.4751 (8) | C5—H9 | 1.091 (2) |
N3—H6 | 1.0535 (16) | C5—H10 | 1.086 (2) |
N3—H7 | 1.0397 (19) | | |
| | | |
C5—N3—H6 | 111.99 (11) | N3—C5—C4 | 111.72 (5) |
C5—N3—H7 | 111.86 (12) | N3—C5—H9 | 108.40 (12) |
C5—N3—H8 | 110.29 (13) | C4—C5—H9 | 108.93 (12) |
O1—C4—O2 | 125.43 (7) | N3—C5—H10 | 109.12 (13) |
O1—C4—C5 | 117.45 (6) | C4—C5—H10 | 110.29 (12) |
O2—C4—C5 | 117.11 (7) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H6···O1i | 1.0535 (16) | 1.7293 (17) | 2.7713 (9) | 169.23 (17) |
N3—H6···O2i | 1.0535 (16) | 2.642 (2) | 3.4242 (11) | 130.75 (12) |
N3—H7···O2ii | 1.0397 (19) | 1.820 (2) | 2.8474 (10) | 168.8 (2) |
N3—H8···O2iii | 1.033 (2) | 2.101 (2) | 3.0650 (12) | 154.26 (17) |
N3—H8···O1iv | 1.033 (2) | 2.362 (2) | 2.9504 (10) | 114.92 (17) |
N3—H8···O1iv | 1.033 (2) | 2.362 (2) | 2.9504 (10) | 114.92 (17) |
Symmetry codes: (i) x, y, z−1; (ii) x+1, y, z; (iii) −x, −y, −z; (iv) −x+1, −y, −z. |
Crystal data top
C8H20N4O8 | F(000) = 62 |
Mr = 300.24 | Dx = 1.613 Mg m−3 Dm = not measusred Mg m−3 Dm measured by not measured |
Monoclinic, P21/n | Neutron radiation, λ = 0.83950 Å |
a = 5.0999 (3) Å | Cell parameters from 1062 reflections |
b = 11.9516 (6) Å | θ = 4.0–46.2° |
c = 5.4594 (3) Å | µ = 0.24 mm−1 |
β = 111.781 (2)° | T = 301 K |
V = 309.00 (3) Å3 | Needle, none |
Z = 1 | 6 × 1.8 × 1.7 mm |
Data collection top
D9 diffractometer | Rint = 0.021 |
Radiation source: ILL reactor | θmax = 46.2°, θmin = 4.0° |
equatorial geometry scans | h = −7→2 |
Absorption correction: gaussian P. Coppens: The evaluation of absorption and extinction in
single crystal structure analysis in crystallographic computing,
ed F.R.Ahmed, Munsgaad, 1970. | k = −13→18 |
Tmin = 0.593, Tmax = 0.706 | l = −7→8 |
1062 measured reflections | 3 standard reflections every 50 reflections |
927 independent reflections | intensity decay: none |
872 reflections with I > 2σ(I) | |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.027 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.061 | w = 1/[σ2(Fo2) + (0.0316P)2 + 0.3176P] where P = (Fo2 + 2Fc2)/3 |
S = 1.15 | (Δ/σ)max < 0.001 |
927 reflections | Δρmax = 0.47 e Å−3 |
92 parameters | Δρmin = −0.44 e Å−3 |
0 restraints | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.583 (17) |
Crystal data top
C8H20N4O8 | V = 309.00 (3) Å3 |
Mr = 300.24 | Z = 1 |
Monoclinic, P21/n | Neutron radiation, λ = 0.83950 Å |
a = 5.0999 (3) Å | µ = 0.24 mm−1 |
b = 11.9516 (6) Å | T = 301 K |
c = 5.4594 (3) Å | 6 × 1.8 × 1.7 mm |
β = 111.781 (2)° | |
Data collection top
D9 diffractometer | 872 reflections with I > 2σ(I) |
Absorption correction: gaussian P. Coppens: The evaluation of absorption and extinction in
single crystal structure analysis in crystallographic computing,
ed F.R.Ahmed, Munsgaad, 1970. | Rint = 0.021 |
Tmin = 0.593, Tmax = 0.706 | 3 standard reflections every 50 reflections |
1062 measured reflections | intensity decay: none |
927 independent reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.027 | 0 restraints |
wR(F2) = 0.061 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.15 | Δρmax = 0.47 e Å−3 |
927 reflections | Δρmin = −0.44 e Å−3 |
92 parameters | |
Special details top
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F2, conventional
R-factors R are based on F, with F set to zero for
negative F2. The threshold expression of F2 >
σ(F2) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F2 are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O1 | 0.30478 (18) | 0.09443 (8) | 0.23515 (15) | 0.02312 (19) | |
O2 | −0.14775 (19) | 0.14154 (9) | 0.10700 (17) | 0.0264 (2) | |
N3 | 0.30086 (10) | 0.08984 (5) | −0.25900 (9) | 0.01986 (14) | |
C4 | 0.07471 (13) | 0.12484 (5) | 0.06601 (12) | 0.01471 (15) | |
C5 | 0.06438 (14) | 0.14494 (6) | −0.21330 (12) | 0.01730 (16) | |
H6 | 0.2894 (4) | 0.10007 (17) | −0.4542 (3) | 0.0339 (4) | |
H7 | 0.4955 (4) | 0.11920 (18) | −0.1307 (3) | 0.0373 (4) | |
H8 | 0.2980 (5) | 0.00493 (15) | −0.2263 (4) | 0.0408 (4) | |
H9 | 0.0775 (5) | 0.23479 (15) | −0.2430 (4) | 0.0424 (4) | |
H10 | −0.1341 (4) | 0.1144 (2) | −0.3568 (3) | 0.0436 (4) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0216 (4) | 0.0360 (4) | 0.0134 (3) | 0.0062 (3) | 0.0084 (3) | 0.0037 (3) |
O2 | 0.0194 (4) | 0.0426 (5) | 0.0219 (4) | 0.0016 (4) | 0.0131 (3) | −0.0027 (3) |
N3 | 0.0198 (2) | 0.0292 (3) | 0.0126 (2) | 0.00562 (18) | 0.00832 (17) | 0.00203 (17) |
C4 | 0.0162 (3) | 0.0172 (3) | 0.0133 (3) | −0.0006 (2) | 0.0085 (2) | −0.0011 (2) |
C5 | 0.0179 (3) | 0.0221 (3) | 0.0134 (3) | 0.0029 (2) | 0.0076 (2) | 0.0033 (2) |
H6 | 0.0343 (8) | 0.0499 (9) | 0.0212 (6) | 0.0052 (7) | 0.0146 (6) | 0.0038 (6) |
H7 | 0.0262 (7) | 0.0576 (10) | 0.0280 (7) | 0.0007 (7) | 0.0098 (6) | −0.0014 (7) |
H8 | 0.0574 (11) | 0.0340 (8) | 0.0323 (8) | 0.0156 (8) | 0.0182 (7) | 0.0028 (6) |
H9 | 0.0632 (12) | 0.0285 (7) | 0.0443 (9) | 0.0124 (8) | 0.0302 (9) | 0.0132 (7) |
H10 | 0.0253 (7) | 0.0763 (13) | 0.0254 (7) | −0.0032 (8) | 0.0050 (6) | −0.0069 (8) |
Geometric parameters (Å, º) top
O1—C4 | 1.2480 (10) | N3—H8 | 1.0315 (19) |
O2—C4 | 1.2512 (10) | C4—C5 | 1.5252 (9) |
N3—C5 | 1.4743 (8) | C5—H9 | 1.0917 (19) |
N3—H6 | 1.0527 (15) | C5—H10 | 1.0879 (18) |
N3—H7 | 1.0408 (18) | | |
| | | |
C5—N3—H6 | 112.21 (11) | N3—C5—C4 | 111.83 (5) |
C5—N3—H7 | 111.81 (12) | N3—C5—H9 | 108.37 (12) |
C5—N3—H8 | 110.20 (12) | C4—C5—H9 | 108.79 (11) |
O1—C4—O2 | 125.45 (7) | N3—C5—H10 | 109.23 (12) |
O1—C4—C5 | 117.38 (6) | C4—C5—H10 | 110.15 (12) |
O2—C4—C5 | 117.16 (7) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H6···O1i | 1.0527 (15) | 1.7277 (16) | 2.7696 (9) | 169.60 (17) |
N3—H6···O2i | 1.0527 (15) | 2.6440 (19) | 3.4234 (10) | 130.56 (12) |
N3—H7···O2ii | 1.0408 (18) | 1.8201 (19) | 2.8482 (10) | 168.73 (19) |
N3—H8···O2iii | 1.0315 (19) | 2.109 (2) | 3.0703 (12) | 154.21 (16) |
N3—H8···O1iv | 1.0315 (19) | 2.364 (2) | 2.9526 (10) | 115.05 (16) |
N3—H8···O1iv | 1.0315 (19) | 2.364 (2) | 2.9526 (10) | 115.05 (16) |
Symmetry codes: (i) x, y, z−1; (ii) x+1, y, z; (iii) −x, −y, −z; (iv) −x+1, −y, −z. |
Crystal data top
C8H20N4O8 | F(000) = 62 |
Mr = 300.24 | Dx = 1.612 Mg m−3 |
Monoclinic, P21/n | Neutron radiation, λ = 0.83950 Å |
a = 5.1008 (3) Å | Cell parameters from 1070 reflections |
b = 11.9558 (8) Å | θ = 4.0–40.0° |
c = 5.4602 (3) Å | µ = 0.24 mm−1 |
β = 111.772 (3)° | T = 304 K |
V = 309.23 (3) Å3 | Needle, none |
Z = 1 | 6 × 1.8 × 1.7 mm |
Data collection top
D9 diffractometer | Rint = 0.018 |
Radiation source: ILL reactor | θmax = 40.0°, θmin = 4.0° |
equatorial geometry scans | h = −7→2 |
Absorption correction: gaussian P. Coppens: The evaluation of absorption and extinction in
single crystal structure analysis in crystallographic computing,
ed F.R.Ahmed, Munsgaad, 1970. | k = −13→18 |
Tmin = 0.593, Tmax = 0.706 | l = −6→8 |
1070 measured reflections | 3 standard reflections every 50 reflections |
926 independent reflections | intensity decay: none |
861 reflections with I > 2σ(I) | |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.027 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.067 | w = 1/[σ2(Fo2) + (0.0408P)2 + 0.3169P] where P = (Fo2 + 2Fc2)/3 |
S = 1.09 | (Δ/σ)max < 0.001 |
926 reflections | Δρmax = 0.47 e Å−3 |
92 parameters | Δρmin = −0.60 e Å−3 |
0 restraints | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.568 (18) |
Crystal data top
C8H20N4O8 | V = 309.23 (3) Å3 |
Mr = 300.24 | Z = 1 |
Monoclinic, P21/n | Neutron radiation, λ = 0.83950 Å |
a = 5.1008 (3) Å | µ = 0.24 mm−1 |
b = 11.9558 (8) Å | T = 304 K |
c = 5.4602 (3) Å | 6 × 1.8 × 1.7 mm |
β = 111.772 (3)° | |
Data collection top
D9 diffractometer | 861 reflections with I > 2σ(I) |
Absorption correction: gaussian P. Coppens: The evaluation of absorption and extinction in
single crystal structure analysis in crystallographic computing,
ed F.R.Ahmed, Munsgaad, 1970. | Rint = 0.018 |
Tmin = 0.593, Tmax = 0.706 | 3 standard reflections every 50 reflections |
1070 measured reflections | intensity decay: none |
926 independent reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.027 | 0 restraints |
wR(F2) = 0.067 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.09 | Δρmax = 0.47 e Å−3 |
926 reflections | Δρmin = −0.60 e Å−3 |
92 parameters | |
Special details top
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F2, conventional
R-factors R are based on F, with F set to zero for
negative F2. The threshold expression of F2 >
σ(F2) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F2 are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O1 | 0.30498 (18) | 0.09419 (8) | 0.23531 (15) | 0.0231 (2) | |
O2 | −0.1475 (2) | 0.14151 (9) | 0.10717 (18) | 0.0272 (2) | |
N3 | 0.30095 (11) | 0.08988 (5) | −0.25906 (9) | 0.02016 (15) | |
C4 | 0.07497 (14) | 0.12485 (5) | 0.06604 (12) | 0.01491 (16) | |
C5 | 0.06457 (15) | 0.14496 (6) | −0.21328 (13) | 0.01742 (17) | |
H6 | 0.2893 (4) | 0.10015 (17) | −0.4544 (3) | 0.0339 (4) | |
H7 | 0.4952 (4) | 0.11908 (19) | −0.1315 (4) | 0.0380 (4) | |
H8 | 0.2982 (5) | 0.00506 (16) | −0.2265 (4) | 0.0408 (4) | |
H9 | 0.0776 (5) | 0.23469 (16) | −0.2431 (4) | 0.0428 (4) | |
H10 | −0.1337 (4) | 0.1148 (2) | −0.3568 (4) | 0.0437 (5) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0214 (4) | 0.0358 (5) | 0.0137 (3) | 0.0059 (3) | 0.0084 (3) | 0.0036 (3) |
O2 | 0.0200 (4) | 0.0442 (5) | 0.0223 (4) | 0.0019 (4) | 0.0136 (3) | −0.0032 (4) |
N3 | 0.0202 (3) | 0.0298 (3) | 0.0126 (2) | 0.00525 (18) | 0.00838 (18) | 0.00155 (17) |
C4 | 0.0165 (3) | 0.0172 (3) | 0.0136 (3) | −0.0010 (2) | 0.0086 (2) | −0.0009 (2) |
C5 | 0.0176 (3) | 0.0225 (3) | 0.0135 (3) | 0.0032 (2) | 0.0073 (2) | 0.0033 (2) |
H6 | 0.0341 (8) | 0.0506 (10) | 0.0205 (6) | 0.0059 (7) | 0.0142 (6) | 0.0043 (6) |
H7 | 0.0252 (7) | 0.0601 (11) | 0.0281 (7) | 0.0005 (7) | 0.0091 (6) | −0.0020 (7) |
H8 | 0.0566 (12) | 0.0344 (9) | 0.0324 (8) | 0.0136 (8) | 0.0177 (8) | 0.0029 (6) |
H9 | 0.0634 (12) | 0.0291 (7) | 0.0444 (10) | 0.0119 (8) | 0.0300 (9) | 0.0135 (7) |
H10 | 0.0255 (8) | 0.0757 (13) | 0.0263 (7) | −0.0030 (8) | 0.0055 (6) | −0.0069 (8) |
Geometric parameters (Å, º) top
O1—C4 | 1.2492 (11) | N3—H8 | 1.030 (2) |
O2—C4 | 1.2520 (11) | C4—C5 | 1.5253 (9) |
N3—C5 | 1.4743 (9) | C5—H9 | 1.091 (2) |
N3—H6 | 1.0533 (16) | C5—H10 | 1.0860 (19) |
N3—H7 | 1.0377 (19) | | |
| | | |
C5—N3—H6 | 112.16 (11) | O2—C4—N3 | 147.85 (6) |
C5—N3—H7 | 111.91 (12) | N3—C5—C4 | 111.83 (5) |
C5—N3—H8 | 110.24 (13) | N3—C5—H9 | 108.35 (12) |
O1—C4—C5 | 117.44 (6) | C4—C5—H9 | 108.85 (12) |
O2—C4—C5 | 117.17 (7) | N3—C5—H10 | 109.29 (13) |
O1—C4—N3 | 85.52 (5) | C4—C5—H10 | 110.31 (12) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H6···O1i | 1.0533 (16) | 1.7269 (17) | 2.7690 (9) | 169.41 (17) |
N3—H6···O2i | 1.0533 (16) | 2.6427 (19) | 3.4230 (11) | 130.62 (13) |
N3—H7···O2ii | 1.0377 (19) | 1.825 (2) | 2.8497 (11) | 168.8 (2) |
N3—H8···O2iii | 1.030 (2) | 2.111 (2) | 3.0716 (13) | 154.13 (17) |
N3—H8···O1iv | 1.030 (2) | 2.362 (2) | 2.9508 (11) | 115.10 (17) |
N3—H8···O1iv | 1.030 (2) | 2.362 (2) | 2.9508 (11) | 115.10 (17) |
Symmetry codes: (i) x, y, z−1; (ii) x+1, y, z; (iii) −x, −y, −z; (iv) −x+1, −y, −z. |
Crystal data top
C8H20N4O8 | F(000) = 62 |
Mr = 300.24 | Dx = 1.611 Mg m−3 |
Monoclinic, P21/n | Neutron radiation, λ = 0.83950 Å |
a = 5.1012 (3) Å | Cell parameters from 1044 reflections |
b = 11.9651 (9) Å | θ = 4.0–40.0° |
c = 5.4604 (4) Å | µ = 0.24 mm−1 |
β = 111.763 (5)° | T = 313 K |
V = 309.53 (4) Å3 | Needle, none |
Z = 1 | 6 × 1.8 × 1.7 mm |
Data collection top
D9 diffractometer | Rint = 0.015 |
Radiation source: ILL reactor | θmax = 40.0°, θmin = 4.0° |
equatorial geometry scans | h = −7→2 |
Absorption correction: gaussian P. Coppens: The evaluation of absorption and extinction in
single crystal structure analysis in crystallographic computing,
ed F.R.Ahmed, Munsgaad, 1970. | k = −13→18 |
Tmin = 0.593, Tmax = 0.706 | l = −6→8 |
1044 measured reflections | 3 standard reflections every 50 reflections |
926 independent reflections | intensity decay: none |
876 reflections with I > 2σ(I) | |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.030 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.074 | w = 1/[σ2(Fo2) + (0.0434P)2 + 0.2935P] where P = (Fo2 + 2Fc2)/3 |
S = 1.16 | (Δ/σ)max < 0.001 |
926 reflections | Δρmax = 0.51 e Å−3 |
92 parameters | Δρmin = −0.55 e Å−3 |
0 restraints | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.60 (2) |
Crystal data top
C8H20N4O8 | V = 309.53 (4) Å3 |
Mr = 300.24 | Z = 1 |
Monoclinic, P21/n | Neutron radiation, λ = 0.83950 Å |
a = 5.1012 (3) Å | µ = 0.24 mm−1 |
b = 11.9651 (9) Å | T = 313 K |
c = 5.4604 (4) Å | 6 × 1.8 × 1.7 mm |
β = 111.763 (5)° | |
Data collection top
D9 diffractometer | 876 reflections with I > 2σ(I) |
Absorption correction: gaussian P. Coppens: The evaluation of absorption and extinction in
single crystal structure analysis in crystallographic computing,
ed F.R.Ahmed, Munsgaad, 1970. | Rint = 0.015 |
Tmin = 0.593, Tmax = 0.706 | 3 standard reflections every 50 reflections |
1044 measured reflections | intensity decay: none |
926 independent reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.030 | 0 restraints |
wR(F2) = 0.074 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.16 | Δρmax = 0.51 e Å−3 |
926 reflections | Δρmin = −0.55 e Å−3 |
92 parameters | |
Special details top
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F2, conventional
R-factors R are based on F, with F set to zero for
negative F2. The threshold expression of F2 >
σ(F2) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F2 are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O1 | 0.3051 (2) | 0.09431 (9) | 0.23518 (16) | 0.0240 (2) | |
O2 | −0.1472 (2) | 0.14152 (10) | 0.1073 (2) | 0.0278 (2) | |
N3 | 0.30130 (12) | 0.09000 (5) | −0.25903 (10) | 0.02068 (17) | |
C4 | 0.07517 (15) | 0.12480 (6) | 0.06600 (14) | 0.01530 (18) | |
C5 | 0.06478 (16) | 0.14495 (7) | −0.21328 (14) | 0.01793 (18) | |
H6 | 0.2897 (4) | 0.10015 (19) | −0.4542 (3) | 0.0348 (4) | |
H7 | 0.4953 (4) | 0.1190 (2) | −0.1309 (4) | 0.0385 (4) | |
H8 | 0.2991 (5) | 0.00493 (17) | −0.2258 (4) | 0.0421 (5) | |
H9 | 0.0778 (5) | 0.23451 (17) | −0.2434 (4) | 0.0439 (5) | |
H10 | −0.1330 (4) | 0.1142 (2) | −0.3567 (4) | 0.0446 (5) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0220 (4) | 0.0380 (5) | 0.0139 (4) | 0.0059 (4) | 0.0086 (3) | 0.0039 (3) |
O2 | 0.0203 (4) | 0.0457 (6) | 0.0227 (4) | 0.0023 (4) | 0.0140 (3) | −0.0026 (4) |
N3 | 0.0211 (3) | 0.0299 (3) | 0.0131 (2) | 0.0057 (2) | 0.00872 (19) | 0.00189 (18) |
C4 | 0.0167 (3) | 0.0176 (3) | 0.0141 (3) | −0.0007 (2) | 0.0087 (2) | −0.0011 (2) |
C5 | 0.0182 (3) | 0.0227 (4) | 0.0143 (3) | 0.0030 (3) | 0.0076 (2) | 0.0037 (2) |
H6 | 0.0346 (9) | 0.0520 (11) | 0.0218 (6) | 0.0059 (7) | 0.0152 (6) | 0.0044 (7) |
H7 | 0.0261 (8) | 0.0605 (12) | 0.0281 (8) | 0.0031 (8) | 0.0092 (6) | −0.0003 (8) |
H8 | 0.0590 (13) | 0.0354 (9) | 0.0333 (9) | 0.0154 (9) | 0.0188 (8) | 0.0029 (7) |
H9 | 0.0662 (14) | 0.0299 (8) | 0.0456 (11) | 0.0116 (9) | 0.0322 (10) | 0.0141 (8) |
H10 | 0.0254 (8) | 0.0785 (15) | 0.0264 (8) | −0.0033 (9) | 0.0056 (7) | −0.0069 (9) |
Geometric parameters (Å, º) top
O1—C4 | 1.2486 (12) | N3—H8 | 1.035 (2) |
O2—C4 | 1.2521 (12) | C4—C5 | 1.5253 (10) |
N3—C5 | 1.4744 (9) | C5—H9 | 1.090 (2) |
N3—H6 | 1.0525 (17) | C5—H10 | 1.087 (2) |
N3—H7 | 1.037 (2) | | |
| | | |
C5—N3—H6 | 112.20 (12) | N3—C5—C4 | 111.82 (6) |
C5—N3—H7 | 111.87 (13) | N3—C5—H9 | 108.26 (13) |
C5—N3—H8 | 110.26 (14) | C4—C5—H9 | 108.95 (13) |
O1—C4—O2 | 125.38 (8) | N3—C5—H10 | 109.07 (14) |
O1—C4—C5 | 117.43 (7) | C4—C5—H10 | 110.23 (13) |
O2—C4—C5 | 117.18 (8) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H6···O1i | 1.0525 (17) | 1.7281 (18) | 2.7696 (10) | 169.54 (19) |
N3—H6···O2i | 1.0525 (17) | 2.644 (2) | 3.4230 (12) | 130.60 (14) |
N3—H7···O2ii | 1.037 (2) | 1.825 (2) | 2.8499 (12) | 168.9 (2) |
N3—H8···O2iii | 1.035 (2) | 2.112 (3) | 3.0759 (14) | 154.01 (19) |
N3—H8···O1iv | 1.035 (2) | 2.359 (2) | 2.9525 (12) | 115.24 (18) |
N3—H8···O1iv | 1.035 (2) | 2.359 (2) | 2.9525 (12) | 115.24 (18) |
Symmetry codes: (i) x, y, z−1; (ii) x+1, y, z; (iii) −x, −y, −z; (iv) −x+1, −y, −z. |
Crystal data top
C8H20N4O8 | F(000) = 62 |
Mr = 300.24 | Dx = 1.609 Mg m−3 |
Monoclinic, P21/n | Neutron radiation, λ = 0.83950 Å |
a = 5.1026 (3) Å | Cell parameters from 926 reflections |
b = 11.9752 (9) Å | θ = 4.0–39.9° |
c = 5.4602 (4) Å | µ = 0.24 mm−1 |
β = 111.757 (5)° | T = 323 K |
V = 309.88 (4) Å3 | Needle, none |
Z = 1 | 6 × 1.8 × 1.7 mm |
Data collection top
D9 diffractometer | Rint = 0.021 |
Radiation source: ILL reactor | θmax = 39.9°, θmin = 4.0° |
equatorial geometry scans | h = −7→2 |
Absorption correction: gaussian P. Coppens: The evaluation of absorption and extinction in
single crystal structure analysis in crystallographic computing,
ed F.R.Ahmed, Munsgaad, 1970. | k = −13→18 |
Tmin = 0.594, Tmax = 0.706 | l = −6→8 |
1060 measured reflections | 3 standard reflections every 50 reflections |
926 independent reflections | intensity decay: none |
883 reflections with I > 2σ(I) | |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.031 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.075 | w = 1/[σ2(Fo2) + (0.0434P)2 + 0.2935P] where P = (Fo2 + 2Fc2)/3 |
S = 1.16 | (Δ/σ)max < 0.001 |
926 reflections | Δρmax = 0.61 e Å−3 |
92 parameters | Δρmin = −0.65 e Å−3 |
0 restraints | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.59 (2) |
Crystal data top
C8H20N4O8 | V = 309.88 (4) Å3 |
Mr = 300.24 | Z = 1 |
Monoclinic, P21/n | Neutron radiation, λ = 0.83950 Å |
a = 5.1026 (3) Å | µ = 0.24 mm−1 |
b = 11.9752 (9) Å | T = 323 K |
c = 5.4602 (4) Å | 6 × 1.8 × 1.7 mm |
β = 111.757 (5)° | |
Data collection top
D9 diffractometer | 883 reflections with I > 2σ(I) |
Absorption correction: gaussian P. Coppens: The evaluation of absorption and extinction in
single crystal structure analysis in crystallographic computing,
ed F.R.Ahmed, Munsgaad, 1970. | Rint = 0.021 |
Tmin = 0.594, Tmax = 0.706 | 3 standard reflections every 50 reflections |
1060 measured reflections | intensity decay: none |
926 independent reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.031 | 0 restraints |
wR(F2) = 0.075 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.16 | Δρmax = 0.61 e Å−3 |
926 reflections | Δρmin = −0.65 e Å−3 |
92 parameters | |
Special details top
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F2, conventional
R-factors R are based on F, with F set to zero for
negative F2. The threshold expression of F2 >
σ(F2) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F2 are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O1 | 0.3055 (2) | 0.09436 (9) | 0.23504 (17) | 0.0250 (2) | |
O2 | −0.1464 (2) | 0.14140 (10) | 0.1074 (2) | 0.0290 (2) | |
N3 | 0.30176 (12) | 0.09010 (5) | −0.25907 (10) | 0.02169 (17) | |
C4 | 0.07555 (15) | 0.12480 (6) | 0.06608 (14) | 0.01603 (18) | |
C5 | 0.06516 (16) | 0.14480 (7) | −0.21328 (14) | 0.01865 (18) | |
H6 | 0.2908 (4) | 0.10024 (19) | −0.4544 (3) | 0.0357 (4) | |
H7 | 0.4960 (4) | 0.1193 (2) | −0.1313 (4) | 0.0398 (4) | |
H8 | 0.2990 (5) | 0.00500 (17) | −0.2260 (4) | 0.0433 (5) | |
H9 | 0.0778 (6) | 0.23443 (17) | −0.2438 (5) | 0.0456 (5) | |
H10 | −0.1321 (4) | 0.1142 (2) | −0.3561 (4) | 0.0467 (5) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0227 (4) | 0.0395 (5) | 0.0146 (4) | 0.0062 (4) | 0.0089 (3) | 0.0045 (3) |
O2 | 0.0207 (4) | 0.0478 (6) | 0.0236 (4) | 0.0016 (4) | 0.0141 (3) | −0.0034 (4) |
N3 | 0.0218 (3) | 0.0319 (3) | 0.0135 (2) | 0.0061 (2) | 0.0090 (2) | 0.00206 (19) |
C4 | 0.0174 (3) | 0.0188 (3) | 0.0144 (3) | −0.0011 (2) | 0.0089 (2) | −0.0013 (2) |
C5 | 0.0189 (3) | 0.0238 (4) | 0.0146 (3) | 0.0031 (3) | 0.0078 (2) | 0.0038 (2) |
H6 | 0.0356 (9) | 0.0538 (11) | 0.0220 (6) | 0.0052 (8) | 0.0157 (6) | 0.0041 (7) |
H7 | 0.0274 (8) | 0.0630 (12) | 0.0290 (8) | 0.0032 (8) | 0.0104 (7) | −0.0013 (8) |
H8 | 0.0597 (13) | 0.0373 (10) | 0.0343 (9) | 0.0153 (9) | 0.0192 (9) | 0.0027 (7) |
H9 | 0.0691 (14) | 0.0306 (8) | 0.0479 (11) | 0.0137 (9) | 0.0343 (11) | 0.0151 (8) |
H10 | 0.0259 (9) | 0.0834 (15) | 0.0269 (8) | −0.0025 (9) | 0.0052 (7) | −0.0072 (9) |
Geometric parameters (Å, º) top
O1—C4 | 1.2484 (12) | N3—H8 | 1.036 (2) |
O2—C4 | 1.2498 (12) | C4—C5 | 1.5255 (10) |
N3—C5 | 1.4741 (9) | C5—H9 | 1.092 (2) |
N3—H6 | 1.0542 (17) | C5—H10 | 1.083 (2) |
N3—H7 | 1.039 (2) | | |
| | | |
C5—N3—H6 | 112.38 (12) | N3—C5—C4 | 111.88 (6) |
C5—N3—H7 | 111.97 (13) | N3—C5—H9 | 108.21 (14) |
C5—N3—H8 | 110.05 (14) | C4—C5—H9 | 108.96 (13) |
O1—C4—O2 | 125.42 (8) | N3—C5—H10 | 109.19 (14) |
O1—C4—C5 | 117.36 (7) | C4—C5—H10 | 110.20 (14) |
O2—C4—C5 | 117.22 (8) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H6···O1i | 1.0542 (17) | 1.7263 (19) | 2.7699 (10) | 169.66 (19) |
N3—H6···O2i | 1.0542 (17) | 2.643 (2) | 3.4218 (12) | 130.39 (14) |
N3—H7···O2ii | 1.039 (2) | 1.826 (2) | 2.8519 (12) | 168.7 (2) |
N3—H8···O2iii | 1.036 (2) | 2.115 (3) | 3.0801 (14) | 154.02 (19) |
N3—H8···O1iv | 1.036 (2) | 2.359 (2) | 2.9524 (12) | 115.20 (18) |
N3—H8···O1iv | 1.036 (2) | 2.359 (2) | 2.9524 (12) | 115.20 (18) |
Symmetry codes: (i) x, y, z−1; (ii) x+1, y, z; (iii) −x, −y, −z; (iv) −x+1, −y, −z. |
Crystal data top
C8H20N4O8 | F(000) = 62 |
Mr = 300.24 | Dx = 1.595 Mg m−3 |
Monoclinic, P21/n | Neutron radiation, λ = 0.83970 Å |
a = 5.1074 (3) Å | Cell parameters from 399 reflections |
b = 12.0775 (9) Å | θ = 4.0–46.2° |
c = 5.4596 (4) Å | µ = 0.24 mm−1 |
β = 111.827 (5)° | T = 427 K |
V = 312.63 (4) Å3 | Needle, none |
Z = 1 | 6 × 1.8 × 1.7 mm |
Data collection top
D9 diffractometer | Rint = 0.093 |
Radiation source: ILL reactor | θmax = 46.2°, θmin = 4.0° |
equatorial geometry scans | h = −5→1 |
Absorption correction: gaussian P. Coppens: The evaluation of absorption and extinction in
single crystal structure analysis in crystallographic computing,
ed F.R.Ahmed, Munsgaad, 1970. | k = −4→12 |
Tmin = 0.594, Tmax = 0.706 | l = −7→6 |
399 measured reflections | 3 standard reflections every 50 reflections |
331 independent reflections | intensity decay: none |
312 reflections with I > 2σ(I) | |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.031 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.072 | w = 1/[σ2(Fo2) + (0.0434P)2 + 0.2935P] where P = (Fo2 + 2Fc2)/3 |
S = 1.33 | (Δ/σ)max = 0.001 |
331 reflections | Δρmax = 0.61 e Å−3 |
92 parameters | Δρmin = −0.35 e Å−3 |
0 restraints | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.26 (2) |
Crystal data top
C8H20N4O8 | V = 312.63 (4) Å3 |
Mr = 300.24 | Z = 1 |
Monoclinic, P21/n | Neutron radiation, λ = 0.83970 Å |
a = 5.1074 (3) Å | µ = 0.24 mm−1 |
b = 12.0775 (9) Å | T = 427 K |
c = 5.4596 (4) Å | 6 × 1.8 × 1.7 mm |
β = 111.827 (5)° | |
Data collection top
D9 diffractometer | 312 reflections with I > 2σ(I) |
Absorption correction: gaussian P. Coppens: The evaluation of absorption and extinction in
single crystal structure analysis in crystallographic computing,
ed F.R.Ahmed, Munsgaad, 1970. | Rint = 0.093 |
Tmin = 0.594, Tmax = 0.706 | 3 standard reflections every 50 reflections |
399 measured reflections | intensity decay: none |
331 independent reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.031 | 0 restraints |
wR(F2) = 0.072 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.33 | Δρmax = 0.61 e Å−3 |
331 reflections | Δρmin = −0.35 e Å−3 |
92 parameters | |
Special details top
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F2, conventional
R-factors R are based on F, with F set to zero for
negative F2. The threshold expression of F2 >
σ(F2) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F2 are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O1 | 0.3093 (5) | 0.09491 (19) | 0.2345 (5) | 0.0292 (8) | |
O2 | −0.1400 (5) | 0.1416 (2) | 0.1074 (5) | 0.0363 (8) | |
N3 | 0.3075 (4) | 0.09064 (19) | −0.2581 (4) | 0.0259 (7) | |
C4 | 0.0819 (4) | 0.12463 (14) | 0.0657 (4) | 0.0171 (7) | |
C5 | 0.0694 (5) | 0.14393 (17) | −0.2138 (4) | 0.0202 (7) | |
H6 | 0.2952 (10) | 0.1021 (4) | −0.4558 (9) | 0.0407 (12) | |
H7 | 0.4978 (13) | 0.1199 (4) | −0.1342 (12) | 0.0482 (12) | |
H8 | 0.3064 (11) | 0.0095 (6) | −0.2283 (9) | 0.0496 (13) | |
H9 | 0.0791 (11) | 0.2327 (4) | −0.2442 (9) | 0.0539 (14) | |
H10 | −0.1257 (13) | 0.1144 (5) | −0.3542 (11) | 0.0570 (14) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0217 (18) | 0.0517 (15) | 0.0169 (13) | 0.0077 (11) | 0.0105 (14) | 0.0049 (10) |
O2 | 0.0201 (16) | 0.0670 (18) | 0.0304 (17) | 0.0048 (12) | 0.0194 (14) | −0.0040 (11) |
N3 | 0.0184 (14) | 0.0489 (15) | 0.0133 (11) | 0.0083 (9) | 0.0093 (10) | 0.0012 (8) |
C4 | 0.0120 (13) | 0.0269 (11) | 0.0157 (11) | −0.0007 (8) | 0.0090 (11) | −0.0013 (8) |
C5 | 0.0131 (15) | 0.0322 (15) | 0.0172 (14) | 0.0065 (9) | 0.0080 (13) | 0.0054 (8) |
H6 | 0.040 (3) | 0.066 (3) | 0.026 (3) | 0.006 (2) | 0.023 (2) | 0.007 (2) |
H7 | 0.021 (3) | 0.085 (3) | 0.039 (3) | 0.003 (3) | 0.012 (3) | 0.001 (2) |
H8 | 0.062 (3) | 0.056 (3) | 0.034 (3) | 0.025 (3) | 0.021 (2) | 0.002 (2) |
H9 | 0.076 (4) | 0.042 (3) | 0.060 (3) | 0.020 (2) | 0.044 (3) | 0.019 (2) |
H10 | 0.023 (3) | 0.109 (4) | 0.035 (3) | −0.004 (3) | 0.006 (3) | −0.006 (2) |
Geometric parameters (Å, º) top
O1—C4 | 1.237 (3) | N3—H8 | 0.993 (8) |
O2—C4 | 1.253 (3) | C4—C5 | 1.521 (3) |
N3—C5 | 1.473 (3) | C5—H9 | 1.089 (6) |
N3—H6 | 1.067 (6) | C5—H10 | 1.068 (8) |
N3—H7 | 1.019 (8) | | |
| | | |
C5—N3—H6 | 111.6 (3) | N3—C5—C4 | 111.62 (18) |
C5—N3—H7 | 112.4 (3) | N3—C5—H9 | 108.6 (3) |
C5—N3—H8 | 110.4 (3) | C4—C5—H9 | 108.5 (3) |
O1—C4—O2 | 125.0 (2) | N3—C5—H10 | 110.1 (3) |
O1—C4—C5 | 117.97 (18) | C4—C5—H10 | 110.4 (3) |
O2—C4—C5 | 116.98 (19) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H6···O1i | 1.067 (6) | 1.721 (5) | 2.774 (2) | 168.3 (4) |
N3—H6···O2i | 1.067 (6) | 2.630 (5) | 3.423 (3) | 130.8 (3) |
N3—H7···O2ii | 1.019 (8) | 1.848 (7) | 2.852 (3) | 167.8 (5) |
N3—H8···O2iii | 0.993 (8) | 2.215 (7) | 3.130 (3) | 152.5 (4) |
N3—H8···O1iv | 0.993 (8) | 2.344 (5) | 2.947 (3) | 118.2 (4) |
N3—H8···O1iv | 0.993 (8) | 2.344 (5) | 2.947 (3) | 118.2 (4) |
Symmetry codes: (i) x, y, z−1; (ii) x+1, y, z; (iii) −x, −y, −z; (iv) −x+1, −y, −z. |
Experimental details
| (288K) | (301K) | (304K) | (313K) |
Crystal data |
Chemical formula | C8H20N4O8 | C8H20N4O8 | C8H20N4O8 | C8H20N4O8 |
Mr | 300.24 | 300.24 | 300.24 | 300.24 |
Crystal system, space group | Monoclinic, P21/n | Monoclinic, P21/n | Monoclinic, P21/n | Monoclinic, P21/n |
Temperature (K) | 288 | 301 | 304 | 313 |
a, b, c (Å) | 5.0993 (3), 11.9416 (6), 5.4608 (3) | 5.0999 (3), 11.9516 (6), 5.4594 (3) | 5.1008 (3), 11.9558 (8), 5.4602 (3) | 5.1012 (3), 11.9651 (9), 5.4604 (4) |
β (°) | 111.784 (2) | 111.781 (2) | 111.772 (3) | 111.763 (5) |
V (Å3) | 308.78 (3) | 309.00 (3) | 309.23 (3) | 309.53 (4) |
Z | 1 | 1 | 1 | 1 |
Radiation type | Neutron, λ = 0.83950 Å | Neutron, λ = 0.83950 Å | Neutron, λ = 0.83950 Å | Neutron, λ = 0.83950 Å |
µ (mm−1) | 0.24 | 0.24 | 0.24 | 0.24 |
Crystal size (mm) | 6 × 1.8 × 1.7 | 6 × 1.8 × 1.7 | 6 × 1.8 × 1.7 | 6 × 1.8 × 1.7 |
|
Data collection |
Diffractometer | D9 diffractometer | D9 diffractometer | D9 diffractometer | D9 diffractometer |
Absorption correction | Gaussian P. Coppens: The evaluation of absorption and extinction in
single crystal structure analysis in crystallographic computing,
ed F.R.Ahmed, Munsgaad, 1970. | Gaussian P. Coppens: The evaluation of absorption and extinction in
single crystal structure analysis in crystallographic computing,
ed F.R.Ahmed, Munsgaad, 1970. | Gaussian P. Coppens: The evaluation of absorption and extinction in
single crystal structure analysis in crystallographic computing,
ed F.R.Ahmed, Munsgaad, 1970. | Gaussian P. Coppens: The evaluation of absorption and extinction in
single crystal structure analysis in crystallographic computing,
ed F.R.Ahmed, Munsgaad, 1970. |
Tmin, Tmax | 0.550, 0.706 | 0.593, 0.706 | 0.593, 0.706 | 0.593, 0.706 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 1540, 1319, 1249 | 1062, 927, 872 | 1070, 926, 861 | 1044, 926, 876 |
Rint | 0.016 | 0.021 | 0.018 | 0.015 |
(sin θ/λ)max (Å−1) | 0.843 | 0.860 | 0.766 | 0.765 |
|
Refinement |
R[F2 > 2σ(F2)], wR(F2), S | 0.037, 0.078, 1.20 | 0.027, 0.061, 1.15 | 0.027, 0.067, 1.09 | 0.030, 0.074, 1.16 |
No. of reflections | 1319 | 927 | 926 | 926 |
No. of parameters | 92 | 92 | 92 | 92 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement | H atoms treated by a mixture of independent and constrained refinement | H atoms treated by a mixture of independent and constrained refinement | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.68, −0.62 | 0.47, −0.44 | 0.47, −0.60 | 0.51, −0.55 |
| (323K) | (427K) |
Crystal data |
Chemical formula | C8H20N4O8 | C8H20N4O8 |
Mr | 300.24 | 300.24 |
Crystal system, space group | Monoclinic, P21/n | Monoclinic, P21/n |
Temperature (K) | 323 | 427 |
a, b, c (Å) | 5.1026 (3), 11.9752 (9), 5.4602 (4) | 5.1074 (3), 12.0775 (9), 5.4596 (4) |
β (°) | 111.757 (5) | 111.827 (5) |
V (Å3) | 309.88 (4) | 312.63 (4) |
Z | 1 | 1 |
Radiation type | Neutron, λ = 0.83950 Å | Neutron, λ = 0.83970 Å |
µ (mm−1) | 0.24 | 0.24 |
Crystal size (mm) | 6 × 1.8 × 1.7 | 6 × 1.8 × 1.7 |
|
Data collection |
Diffractometer | D9 diffractometer | D9 diffractometer |
Absorption correction | Gaussian P. Coppens: The evaluation of absorption and extinction in
single crystal structure analysis in crystallographic computing,
ed F.R.Ahmed, Munsgaad, 1970. | Gaussian P. Coppens: The evaluation of absorption and extinction in
single crystal structure analysis in crystallographic computing,
ed F.R.Ahmed, Munsgaad, 1970. |
Tmin, Tmax | 0.594, 0.706 | 0.594, 0.706 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 1060, 926, 883 | 399, 331, 312 |
Rint | 0.021 | 0.093 |
(sin θ/λ)max (Å−1) | 0.765 | 0.860 |
|
Refinement |
R[F2 > 2σ(F2)], wR(F2), S | 0.031, 0.075, 1.16 | 0.031, 0.072, 1.33 |
No. of reflections | 926 | 331 |
No. of parameters | 92 | 92 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.61, −0.65 | 0.61, −0.35 |
Hydrogen-bond geometry (Å, º) for (288K) top
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H6···O1i | 1.0535 (16) | 1.7293 (17) | 2.7713 (9) | 169.23 (17) |
N3—H6···O2i | 1.0535 (16) | 2.642 (2) | 3.4242 (11) | 130.75 (12) |
N3—H7···O2ii | 1.0397 (19) | 1.820 (2) | 2.8474 (10) | 168.8 (2) |
N3—H8···O2iii | 1.033 (2) | 2.101 (2) | 3.0650 (12) | 154.26 (17) |
N3—H8···O1iv | 1.033 (2) | 2.362 (2) | 2.9504 (10) | 114.92 (17) |
N3—H8···O1iv | 1.033 (2) | 2.362 (2) | 2.9504 (10) | 114.92 (17) |
Symmetry codes: (i) x, y, z−1; (ii) x+1, y, z; (iii) −x, −y, −z; (iv) −x+1, −y, −z. |
Hydrogen-bond geometry (Å, º) for (301K) top
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H6···O1i | 1.0527 (15) | 1.7277 (16) | 2.7696 (9) | 169.60 (17) |
N3—H6···O2i | 1.0527 (15) | 2.6440 (19) | 3.4234 (10) | 130.56 (12) |
N3—H7···O2ii | 1.0408 (18) | 1.8201 (19) | 2.8482 (10) | 168.73 (19) |
N3—H8···O2iii | 1.0315 (19) | 2.109 (2) | 3.0703 (12) | 154.21 (16) |
N3—H8···O1iv | 1.0315 (19) | 2.364 (2) | 2.9526 (10) | 115.05 (16) |
N3—H8···O1iv | 1.0315 (19) | 2.364 (2) | 2.9526 (10) | 115.05 (16) |
Symmetry codes: (i) x, y, z−1; (ii) x+1, y, z; (iii) −x, −y, −z; (iv) −x+1, −y, −z. |
Hydrogen-bond geometry (Å, º) for (304K) top
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H6···O1i | 1.0533 (16) | 1.7269 (17) | 2.7690 (9) | 169.41 (17) |
N3—H6···O2i | 1.0533 (16) | 2.6427 (19) | 3.4230 (11) | 130.62 (13) |
N3—H7···O2ii | 1.0377 (19) | 1.825 (2) | 2.8497 (11) | 168.8 (2) |
N3—H8···O2iii | 1.030 (2) | 2.111 (2) | 3.0716 (13) | 154.13 (17) |
N3—H8···O1iv | 1.030 (2) | 2.362 (2) | 2.9508 (11) | 115.10 (17) |
N3—H8···O1iv | 1.030 (2) | 2.362 (2) | 2.9508 (11) | 115.10 (17) |
Symmetry codes: (i) x, y, z−1; (ii) x+1, y, z; (iii) −x, −y, −z; (iv) −x+1, −y, −z. |
Hydrogen-bond geometry (Å, º) for (313K) top
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H6···O1i | 1.0525 (17) | 1.7281 (18) | 2.7696 (10) | 169.54 (19) |
N3—H6···O2i | 1.0525 (17) | 2.644 (2) | 3.4230 (12) | 130.60 (14) |
N3—H7···O2ii | 1.037 (2) | 1.825 (2) | 2.8499 (12) | 168.9 (2) |
N3—H8···O2iii | 1.035 (2) | 2.112 (3) | 3.0759 (14) | 154.01 (19) |
N3—H8···O1iv | 1.035 (2) | 2.359 (2) | 2.9525 (12) | 115.24 (18) |
N3—H8···O1iv | 1.035 (2) | 2.359 (2) | 2.9525 (12) | 115.24 (18) |
Symmetry codes: (i) x, y, z−1; (ii) x+1, y, z; (iii) −x, −y, −z; (iv) −x+1, −y, −z. |
Hydrogen-bond geometry (Å, º) for (323K) top
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H6···O1i | 1.0542 (17) | 1.7263 (19) | 2.7699 (10) | 169.66 (19) |
N3—H6···O2i | 1.0542 (17) | 2.643 (2) | 3.4218 (12) | 130.39 (14) |
N3—H7···O2ii | 1.039 (2) | 1.826 (2) | 2.8519 (12) | 168.7 (2) |
N3—H8···O2iii | 1.036 (2) | 2.115 (3) | 3.0801 (14) | 154.02 (19) |
N3—H8···O1iv | 1.036 (2) | 2.359 (2) | 2.9524 (12) | 115.20 (18) |
N3—H8···O1iv | 1.036 (2) | 2.359 (2) | 2.9524 (12) | 115.20 (18) |
Symmetry codes: (i) x, y, z−1; (ii) x+1, y, z; (iii) −x, −y, −z; (iv) −x+1, −y, −z. |
Hydrogen-bond geometry (Å, º) for (427K) top
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H6···O1i | 1.067 (6) | 1.721 (5) | 2.774 (2) | 168.3 (4) |
N3—H6···O2i | 1.067 (6) | 2.630 (5) | 3.423 (3) | 130.8 (3) |
N3—H7···O2ii | 1.019 (8) | 1.848 (7) | 2.852 (3) | 167.8 (5) |
N3—H8···O2iii | 0.993 (8) | 2.215 (7) | 3.130 (3) | 152.5 (4) |
N3—H8···O1iv | 0.993 (8) | 2.344 (5) | 2.947 (3) | 118.2 (4) |
N3—H8···O1iv | 0.993 (8) | 2.344 (5) | 2.947 (3) | 118.2 (4) |
Symmetry codes: (i) x, y, z−1; (ii) x+1, y, z; (iii) −x, −y, −z; (iv) −x+1, −y, −z. |