Nanotubes of l-isoleucyl-l-leucine 0.91-hydrate

Görbitz, C.H.

doi:10.1107/S1600536804006427

Nanotubes of L-isoleucyl-L-leucine 0.91-hydrate

As the only dipeptide containing an L-Ile residue, the title compound, C₁₂H₂₄N₂O₃·0.91H₂O, forms nanotubes with hydrophilic inner surfaces. There are two dipeptide molecules in the asymmetric unit, together with disordered water molecules.

Read article Similar articles

Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804006427/cf6339sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536804006427/cf6339Isup2.hkl Contains datablock I

CCDC reference: 238805

checkCIF report

Key indicators

Single-crystal X-ray study
T = 105 K
Mean (C-C) = 0.004 Å
Disorder in solvent or counterion
R factor = 0.038
wR factor = 0.095
Data-to-parameter ratio = 8.1

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT063_ALERT_3_A Crystal Probably too Large for Beam Size .......       1.35 mm

Author Response: This is no problem for a light atom structure, see Gorbitz, Acta Cryst. B55 (1999) 1090-98.


Alert level B
CRYSS02_ALERT_3_B  The value of _exptl_crystal_size_max is > 1.0
   Maximum crystal size given =   1.350
PLAT222_ALERT_3_B Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       4.08 Ratio
PLAT222_ALERT_3_B Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       4.29 Ratio
PLAT420_ALERT_2_B D-H Without Acceptor      >O1C    -  >H12C   ...          ?

Alert level C
PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings    Differ ....          ?
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT045_ALERT_1_C Calculated and Reported Z Differ by ............       0.50 Ratio
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.12 Ratio
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.45 Ratio
PLAT242_ALERT_2_C Check Low    U(eq) as Compared to Neighbors ....        C2B
PLAT302_ALERT_4_C Anion/Solvent Disorder .........................      46.00 Perc.
PLAT417_ALERT_2_C Short Inter D-H..H-D       H1A    ..  H12E    ..       2.12 Ang.
PLAT432_ALERT_2_C Short Inter X...Y Contact  C1B    ..  O1F     ..       3.00 Ang.

Alert level G
FORMU01_ALERT_1_G  There is a discrepancy between the atom counts in the
            _chemical_formula_sum and _chemical_formula_moiety. This is
            usually due to the moiety formula being in the wrong format.
            Atom count from _chemical_formula_sum:   C12 H25.83 N2 O3.91
            Atom count from _chemical_formula_moiety:C12 H25.82 N2 O3.91
CELLZ01_ALERT_1_G Difference between formula and atom_site contents detected.
CELLZ01_ALERT_1_G ALERT: check formula stoichiometry or atom site occupancies.
           From the CIF: _cell_formula_units_Z    8
           From the CIF: _chemical_formula_sum  C12 H25.83 N2 O3.91
           TEST: Compare cell contents of formula and atom_site data

           atom    Z*formula  cif sites diff
           C         96.00     96.00    0.00
           H        206.64    206.61    0.03
           N         16.00     16.00    0.00
           O         31.28     31.30   -0.02
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           26.37
           From the CIF: _reflns_number_total               3390
           Count of symmetry unique reflns         3426
           Completeness (_total/calc)             98.95%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured         0
           Fraction of Friedel pairs measured     0.000
           Are heavy atom types Z>Si present           no

   1 ALERT level A = In general: serious problem
   4 ALERT level B = Potentially serious problem
  10 ALERT level C = Check and explain
   4 ALERT level G = General alerts; check

   6 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   6 ALERT type 2 Indicator that the structure model may be wrong or deficient
   4 ALERT type 3 Indicator that the structure quality may be low
   3 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT+ (Bruker, 2001); data reduction: SAINT+; program(s) used to solve structure: SHELXTL (Bruker, 2000); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

(I) top

Crystal data top

C₁₂H₂₄N₂O₃·0.91H₂O	F(000) = 1145
M_r = 260.82	D_x = 1.155 Mg m⁻³
Monoclinic, C2	Mo Kα radiation, λ = 0.71073 Å
a = 34.243 (2) Å	Cell parameters from 4227 reflections
b = 5.3251 (4) Å	θ = 2.3–26.4°
c = 18.1469 (12) Å	µ = 0.09 mm⁻¹
β = 114.830 (2)°	T = 105 K
V = 3003.1 (4) Å³	Flat needle, colorless
Z = 8	1.35 × 0.01 × 0.002 mm

Data collection top

Bruker SMART CCD diffractometer	3390 independent reflections
Radiation source: fine-focus sealed tube	2948 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.025
Detector resolution: 8.3 pixels mm^-1	θ_max = 26.4°, θ_min = 2.3°
ω scans	h = −42→42
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −6→6
T_min = 0.857, T_max = 1.000	l = −22→15
8896 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.095	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ²(F_o²) + (0.0448P)² + 1.7788P] where P = (F_o² + 2F_c²)/3
3390 reflections	(Δ/σ)_max = 0.004
416 parameters	Δρ_max = 0.36 e Å⁻³
38 restraints	Δρ_min = −0.37 e Å⁻³

Special details top

Experimental. Data were collected by measuring three sets of exposures with the detector set at 2θ = 28°, crystal-to-detector distance 5.00 cm.

Refinement. Refinement of F² against ALL reflections.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
O1A	0.31097 (6)	0.2952 (3)	0.33347 (10)	0.0280 (4)
O2A	0.21621 (6)	0.3490 (4)	0.20785 (17)	0.0572 (7)
O3A	0.24751 (6)	0.0642 (3)	0.16105 (10)	0.0325 (4)
N1A	0.31778 (8)	0.6046 (5)	0.46151 (12)	0.0295 (5)
H1A	0.2884 (8)	0.653 (7)	0.4467 (17)	0.044*
H2A	0.3376 (9)	0.665 (6)	0.5161 (16)	0.044*
H3A	0.3209 (10)	0.432 (6)	0.4657 (18)	0.044*
N2A	0.29137 (6)	0.6357 (4)	0.25068 (11)	0.0206 (4)
H4A	0.2885 (8)	0.793 (6)	0.2468 (15)	0.025*
C1A	0.33024 (8)	0.6993 (5)	0.39631 (14)	0.0250 (5)
H11A	0.3199 (8)	0.862 (7)	0.3844 (16)	0.030*
C2A	0.37995 (8)	0.7085 (5)	0.42704 (14)	0.0277 (5)
H21A	0.3910	0.829	0.4723	0.033*
C3A	0.40159 (9)	0.4576 (6)	0.45924 (17)	0.0425 (7)
H31A	0.4332	0.482	0.4881	0.064*
H32A	0.3952	0.339	0.4132	0.064*
H33A	0.3905	0.387	0.4975	0.064*
C4A	0.39169 (8)	0.8098 (6)	0.35984 (15)	0.0332 (6)
H41A	0.3833	0.686	0.3159	0.040*
H42A	0.3751	0.964	0.3375	0.040*
C5A	0.43971 (9)	0.8679 (8)	0.3891 (2)	0.0521 (9)
H51A	0.4449	0.955	0.3428	0.078*
H52A	0.4572	0.701	0.4052	0.078*
H53A	0.4496	0.986	0.4393	0.078*
C6A	0.30965 (7)	0.5242 (5)	0.32362 (14)	0.0233 (5)
C7A	0.27373 (7)	0.4899 (5)	0.17525 (13)	0.0217 (5)
H71A	0.2547 (8)	0.611 (6)	0.1328 (15)	0.026*
C8A	0.30944 (8)	0.3960 (5)	0.15297 (14)	0.0287 (5)
H81A	0.2970	0.279	0.1071	0.034*
H82A	0.3305	0.302	0.1991	0.034*
C9A	0.33283 (8)	0.6066 (6)	0.13008 (14)	0.0349 (6)
H91A	0.3392	0.743	0.1712	0.042*
C10A	0.37563 (10)	0.5107 (10)	0.1335 (2)	0.0678 (12)
H12A	0.3904	0.647	0.1193	0.102*
H13A	0.3703	0.372	0.0949	0.102*
H14A	0.3937	0.451	0.1885	0.102*
C11A	0.30522 (10)	0.7180 (7)	0.04670 (16)	0.0472 (8)
H15A	0.3213	0.854	0.0345	0.071*
H16A	0.2784	0.787	0.0467	0.071*
H17A	0.2980	0.585	0.0049	0.071*
C12A	0.24374 (8)	0.2828 (5)	0.18207 (15)	0.0301 (6)
O1B	0.13513 (6)	0.5163 (3)	0.24286 (11)	0.0313 (4)
O2B	0.16874 (5)	0.6239 (4)	0.43263 (11)	0.0373 (4)
O3B	0.12388 (5)	0.2976 (3)	0.39624 (9)	0.0269 (4)
N1B	0.19545 (7)	0.8304 (5)	0.22538 (14)	0.0320 (5)
H1B	0.2101 (9)	0.849 (7)	0.2829 (16)	0.048*
H2B	0.2084 (10)	0.931 (6)	0.1987 (18)	0.048*
H3B	0.1985 (10)	0.655 (6)	0.2168 (19)	0.048*
N2B	0.11182 (7)	0.8549 (4)	0.28732 (13)	0.0254 (5)
H4B	0.1145 (9)	1.006 (6)	0.2963 (17)	0.030*
C1B	0.15068 (8)	0.9192 (5)	0.20264 (15)	0.0279 (5)
H11B	0.1527 (9)	1.086 (6)	0.2234 (16)	0.033*
C2B	0.12530 (8)	0.9254 (6)	0.10936 (15)	0.0320 (6)
H21B	0.1394	1.048	0.0888	0.038*
C3B	0.12603 (17)	0.6754 (7)	0.06939 (19)	0.0757 (14)
H31B	0.1122	0.694	0.0120	0.114*
H32B	0.1114	0.552	0.0862	0.114*
H33B	0.1550	0.624	0.0850	0.114*
C4B	0.08005 (9)	1.0230 (9)	0.08867 (19)	0.0568 (10)
H41B	0.0819	1.168	0.1214	0.068*
H42B	0.0641	0.897	0.1021	0.068*
C5B	0.05564 (10)	1.0931 (12)	−0.0013 (2)	0.0801 (16)
H51B	0.0301	1.188	−0.0088	0.120*
H52B	0.0473	0.941	−0.0337	0.120*
H53B	0.0740	1.194	−0.0181	0.120*
C6B	0.13159 (8)	0.7456 (5)	0.24571 (15)	0.0256 (5)
C7B	0.09626 (7)	0.7001 (5)	0.33593 (14)	0.0232 (5)
H71B	0.0898	0.815	0.3717	0.028*
C8B	0.05440 (7)	0.5623 (5)	0.28430 (14)	0.0282 (5)
H81B	0.0593	0.456	0.2442	0.034*
H82B	0.0472	0.449	0.3201	0.034*
C9B	0.01581 (8)	0.7329 (6)	0.23883 (16)	0.0364 (7)
H91B	0.0234	0.849	0.2048	0.044*
C10B	−0.02244 (9)	0.5729 (8)	0.1835 (2)	0.0583 (9)
H12B	−0.0143	0.477	0.1437	0.087*
H13B	−0.0479	0.686	0.1525	0.087*
H14B	−0.0304	0.450	0.2176	0.087*
C11B	0.00338 (9)	0.8878 (7)	0.2968 (2)	0.0476 (8)
H15B	0.0274	1.002	0.3290	0.071*
H16B	−0.0026	0.773	0.3340	0.071*
H17B	−0.0227	0.988	0.2650	0.071*
C12B	0.13264 (7)	0.5234 (5)	0.39157 (14)	0.0240 (5)
O1C	0.23379 (8)	0.8516 (7)	0.40311 (17)	0.0529 (8)	0.827 (3)
H11C	0.2150	0.793	0.4179	0.079*	0.827 (3)
H12C	0.2356	1.006	0.4153	0.079*	0.827 (3)
O1D	0.23030 (10)	0.3426 (11)	0.38218 (19)	0.0671 (16)	0.653 (5)
H11D	0.2212	0.317	0.3316	0.101*	0.653 (5)
H12D	0.2093	0.405	0.3891	0.101*	0.653 (5)
O1E	0.2352 (3)	0.331 (2)	0.4868 (6)	0.032 (2)*	0.173 (3)
H11E	0.2135	0.428	0.4668	0.049*	0.173 (3)
H12E	0.2569	0.427	0.5016	0.049*	0.173 (3)
O1F	0.2030 (4)	1.046 (3)	0.3780 (7)	0.043 (3)*	0.173 (3)
H11F	0.1885	0.917	0.3792	0.064*	0.173 (3)
H12F	0.1887	1.170	0.3840	0.064*	0.173 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1A	0.0384 (9)	0.0185 (9)	0.0239 (8)	0.0012 (8)	0.0100 (7)	0.0035 (7)
O2A	0.0346 (10)	0.0265 (12)	0.124 (2)	0.0037 (9)	0.0467 (13)	0.0104 (12)
O3A	0.0450 (10)	0.0208 (10)	0.0246 (8)	−0.0040 (8)	0.0076 (7)	0.0000 (7)
N1A	0.0393 (11)	0.0288 (12)	0.0219 (10)	−0.0083 (11)	0.0144 (9)	−0.0014 (10)
N2A	0.0263 (9)	0.0152 (10)	0.0208 (9)	0.0013 (9)	0.0104 (7)	0.0011 (9)
C1A	0.0320 (13)	0.0215 (13)	0.0234 (11)	−0.0018 (11)	0.0134 (10)	0.0022 (10)
C2A	0.0300 (12)	0.0294 (14)	0.0216 (11)	−0.0050 (11)	0.0088 (10)	−0.0024 (10)
C3A	0.0396 (15)	0.0442 (19)	0.0335 (14)	0.0054 (14)	0.0055 (12)	0.0075 (13)
C4A	0.0339 (13)	0.0377 (15)	0.0310 (13)	−0.0037 (13)	0.0166 (11)	−0.0004 (12)
C5A	0.0381 (15)	0.067 (3)	0.0581 (19)	−0.0067 (17)	0.0268 (14)	−0.0043 (19)
C6A	0.0252 (12)	0.0232 (13)	0.0234 (11)	−0.0010 (10)	0.0121 (9)	0.0024 (10)
C7A	0.0216 (10)	0.0192 (12)	0.0206 (11)	0.0010 (9)	0.0053 (9)	0.0002 (9)
C8A	0.0309 (12)	0.0310 (14)	0.0240 (11)	0.0047 (12)	0.0114 (10)	−0.0025 (11)
C9A	0.0326 (12)	0.0499 (18)	0.0254 (12)	−0.0052 (13)	0.0155 (10)	−0.0042 (13)
C10A	0.0437 (17)	0.109 (4)	0.064 (2)	0.003 (2)	0.0359 (16)	0.005 (2)
C11A	0.0541 (17)	0.059 (2)	0.0297 (14)	−0.0124 (16)	0.0188 (13)	0.0022 (14)
C12A	0.0245 (12)	0.0226 (14)	0.0343 (13)	0.0001 (11)	0.0037 (10)	0.0067 (11)
O1B	0.0429 (10)	0.0206 (10)	0.0409 (10)	0.0000 (8)	0.0279 (9)	−0.0036 (8)
O2B	0.0254 (8)	0.0311 (11)	0.0467 (11)	−0.0045 (8)	0.0065 (8)	−0.0059 (9)
O3B	0.0316 (9)	0.0233 (10)	0.0224 (8)	−0.0034 (8)	0.0080 (7)	−0.0004 (7)
N1B	0.0311 (11)	0.0359 (14)	0.0341 (11)	0.0010 (11)	0.0186 (9)	0.0056 (11)
N2B	0.0322 (10)	0.0186 (11)	0.0309 (11)	−0.0007 (9)	0.0186 (9)	−0.0030 (9)
C1B	0.0333 (12)	0.0228 (13)	0.0332 (13)	0.0012 (11)	0.0194 (11)	−0.0012 (12)
C2B	0.0372 (13)	0.0290 (14)	0.0328 (13)	0.0001 (12)	0.0178 (11)	0.0048 (12)
C3B	0.145 (4)	0.040 (2)	0.0278 (15)	0.009 (2)	0.0224 (19)	0.0014 (15)
C4B	0.0323 (14)	0.094 (3)	0.0478 (17)	0.0044 (18)	0.0208 (13)	0.029 (2)
C5B	0.0346 (15)	0.147 (5)	0.055 (2)	0.014 (2)	0.0153 (14)	0.041 (3)
C6B	0.0297 (12)	0.0219 (14)	0.0287 (12)	−0.0008 (10)	0.0157 (10)	−0.0018 (10)
C7B	0.0252 (11)	0.0223 (12)	0.0261 (11)	−0.0005 (10)	0.0146 (10)	−0.0039 (10)
C8B	0.0252 (11)	0.0281 (14)	0.0298 (12)	−0.0009 (11)	0.0102 (10)	−0.0018 (11)
C9B	0.0278 (13)	0.0404 (17)	0.0373 (14)	0.0010 (12)	0.0099 (11)	0.0119 (13)
C10B	0.0328 (15)	0.070 (3)	0.0518 (18)	0.0063 (17)	−0.0022 (13)	−0.0055 (19)
C11B	0.0329 (14)	0.0399 (18)	0.067 (2)	0.0053 (14)	0.0187 (14)	−0.0010 (17)
C12B	0.0252 (12)	0.0248 (13)	0.0239 (11)	−0.0001 (10)	0.0120 (9)	−0.0048 (10)
O1C	0.0314 (13)	0.089 (2)	0.0423 (14)	0.0050 (15)	0.0195 (11)	0.0044 (16)
O1D	0.0373 (18)	0.129 (4)	0.0359 (18)	0.028 (2)	0.0164 (14)	−0.005 (2)

Geometric parameters (Å, º) top

O1A—C6A	1.230 (3)	N1B—H1B	0.95 (3)
O2A—C12A	1.266 (3)	N1B—H2B	0.95 (3)
O3A—C12A	1.248 (3)	N1B—H3B	0.96 (3)
N1A—C1A	1.503 (3)	N2B—C6B	1.340 (3)
N1A—H1A	0.96 (2)	N2B—C7B	1.462 (3)
N1A—H2A	0.99 (3)	N2B—H4B	0.82 (3)
N1A—H3A	0.92 (3)	C1B—C6B	1.524 (3)
N2A—C6A	1.342 (3)	C1B—C2B	1.545 (3)
N2A—C7A	1.465 (3)	C1B—H11B	0.96 (3)
N2A—H4A	0.84 (3)	C2B—C3B	1.521 (5)
C1A—C6A	1.525 (3)	C2B—C4B	1.524 (4)
C1A—C2A	1.553 (3)	C2B—H21B	0.972
C1A—H11A	0.93 (3)	C3B—H31B	0.951
C2A—C3A	1.520 (4)	C3B—H32B	0.951
C2A—C4A	1.534 (3)	C3B—H33B	0.951
C2A—H21A	0.985	C4B—C5B	1.535 (4)
C3A—H31A	0.994	C4B—H41B	0.961
C3A—H32A	0.994	C4B—H42B	0.961
C3A—H33A	0.994	C5B—H51B	0.969
C4A—C5A	1.532 (4)	C5B—H52B	0.969
C4A—H41A	0.982	C5B—H53B	0.969
C4A—H42A	0.982	C7B—C8B	1.531 (3)
C5A—H51A	1.041	C7B—C12B	1.549 (3)
C5A—H52A	1.041	C7B—H71B	0.981
C5A—H53A	1.041	C8B—C9B	1.529 (3)
C7A—C8A	1.525 (3)	C8B—H81B	0.990
C7A—C12A	1.547 (3)	C8B—H82B	0.990
C7A—H71A	1.01 (3)	C9B—C11B	1.531 (4)
C8A—C9A	1.533 (4)	C9B—C10B	1.532 (4)
C8A—H81A	0.981	C9B—H91B	0.982
C8A—H82A	0.981	C10B—H12B	1.013
C9A—C11A	1.528 (4)	C10B—H13B	1.013
C9A—C10A	1.528 (4)	C10B—H14B	1.013
C9A—H91A	1.000	C11B—H15B	0.992
C10A—H12A	0.981	C11B—H16B	0.992
C10A—H13A	0.981	C11B—H17B	0.992
C10A—H14A	0.981	O1C—H11C	0.854
C11A—H15A	0.988	O1C—H12C	0.848
C11A—H16A	0.988	O1D—H11D	0.847
C11A—H17A	0.988	O1D—H12D	0.848
O1B—C6B	1.230 (3)	O1E—H11E	0.851
O2B—C12B	1.263 (3)	O1E—H12E	0.850
O3B—C12B	1.251 (3)	O1F—H11F	0.852
N1B—C1B	1.488 (3)	O1F—H12F	0.853

C1A—N1A—H1A	107.5 (18)	H1B—N1B—H2B	111 (3)
C1A—N1A—H2A	112.2 (18)	C1B—N1B—H3B	115.7 (19)
H1A—N1A—H2A	113 (3)	H1B—N1B—H3B	104 (3)
C1A—N1A—H3A	109.6 (19)	H2B—N1B—H3B	111 (3)
H1A—N1A—H3A	111 (3)	C6B—N2B—C7B	119.6 (2)
H2A—N1A—H3A	104 (3)	C6B—N2B—H4B	120 (2)
C6A—N2A—C7A	121.7 (2)	C7B—N2B—H4B	118 (2)
C6A—N2A—H4A	120.8 (18)	N1B—C1B—C6B	106.2 (2)
C7A—N2A—H4A	117.4 (18)	N1B—C1B—C2B	110.5 (2)
N1A—C1A—C6A	107.2 (2)	C6B—C1B—C2B	114.2 (2)
N1A—C1A—C2A	111.00 (19)	N1B—C1B—H11B	107.0 (17)
C6A—C1A—C2A	111.6 (2)	C6B—C1B—H11B	109.7 (16)
N1A—C1A—H11A	106.9 (17)	C2B—C1B—H11B	109.0 (17)
C6A—C1A—H11A	112.3 (17)	C3B—C2B—C4B	113.6 (3)
C2A—C1A—H11A	107.8 (17)	C3B—C2B—C1B	112.9 (2)
C3A—C2A—C4A	111.5 (2)	C4B—C2B—C1B	108.8 (2)
C3A—C2A—C1A	113.2 (2)	C3B—C2B—H21B	107.0
C4A—C2A—C1A	109.84 (19)	C4B—C2B—H21B	107.0
C3A—C2A—H21A	107.3	C1B—C2B—H21B	107.0
C4A—C2A—H21A	107.3	C2B—C3B—H31B	109.5
C1A—C2A—H21A	107.3	C2B—C3B—H32B	109.5
C2A—C3A—H31A	109.5	H31B—C3B—H32B	109.5
C2A—C3A—H32A	109.5	C2B—C3B—H33B	109.5
H31A—C3A—H32A	109.5	H31B—C3B—H33B	109.5
C2A—C3A—H33A	109.5	H32B—C3B—H33B	109.5
H31A—C3A—H33A	109.5	C2B—C4B—C5B	112.8 (3)
H32A—C3A—H33A	109.5	C2B—C4B—H41B	109.0
C5A—C4A—C2A	113.4 (2)	C5B—C4B—H41B	109.0
C5A—C4A—H41A	108.9	C2B—C4B—H42B	109.0
C2A—C4A—H41A	108.9	C5B—C4B—H42B	109.0
C5A—C4A—H42A	108.9	H41B—C4B—H42B	107.8
C2A—C4A—H42A	108.9	C4B—C5B—H51B	109.5
H41A—C4A—H42A	107.7	C4B—C5B—H52B	109.5
C4A—C5A—H51A	109.5	H51B—C5B—H52B	109.5
C4A—C5A—H52A	109.5	C4B—C5B—H53B	109.5
H51A—C5A—H52A	109.5	H51B—C5B—H53B	109.5
C4A—C5A—H53A	109.5	H52B—C5B—H53B	109.5
H51A—C5A—H53A	109.5	O1B—C6B—N2B	122.4 (2)
H52A—C5A—H53A	109.5	O1B—C6B—C1B	120.6 (2)
O1A—C6A—N2A	123.7 (2)	N2B—C6B—C1B	116.9 (2)
O1A—C6A—C1A	120.3 (2)	N2B—C7B—C8B	112.70 (19)
N2A—C6A—C1A	115.9 (2)	N2B—C7B—C12B	109.80 (18)
N2A—C7A—C8A	111.09 (18)	C8B—C7B—C12B	113.4 (2)
N2A—C7A—C12A	109.28 (19)	N2B—C7B—H71B	106.8
C8A—C7A—C12A	114.9 (2)	C8B—C7B—H71B	106.8
N2A—C7A—H71A	104.8 (16)	C12B—C7B—H71B	106.8
C8A—C7A—H71A	109.9 (14)	C9B—C8B—C7B	114.9 (2)
C12A—C7A—H71A	106.3 (15)	C9B—C8B—H81B	108.6
C7A—C8A—C9A	113.6 (2)	C7B—C8B—H81B	108.6
C7A—C8A—H81A	108.8	C9B—C8B—H82B	108.6
C9A—C8A—H81A	108.8	C7B—C8B—H82B	108.6
C7A—C8A—H82A	108.8	H81B—C8B—H82B	107.5
C9A—C8A—H82A	108.8	C8B—C9B—C11B	112.1 (2)
H81A—C8A—H82A	107.7	C8B—C9B—C10B	109.3 (3)
C11A—C9A—C10A	110.7 (2)	C11B—C9B—C10B	110.0 (2)
C11A—C9A—C8A	112.1 (2)	C8B—C9B—H91B	108.5
C10A—C9A—C8A	110.2 (3)	C11B—C9B—H91B	108.5
C11A—C9A—H91A	107.9	C10B—C9B—H91B	108.5
C10A—C9A—H91A	107.9	C9B—C10B—H12B	109.5
C8A—C9A—H91A	107.9	C9B—C10B—H13B	109.5
C9A—C10A—H12A	109.5	H12B—C10B—H13B	109.5
C9A—C10A—H13A	109.5	C9B—C10B—H14B	109.5
H12A—C10A—H13A	109.5	H12B—C10B—H14B	109.5
C9A—C10A—H14A	109.5	H13B—C10B—H14B	109.5
H12A—C10A—H14A	109.5	C9B—C11B—H15B	109.5
H13A—C10A—H14A	109.5	C9B—C11B—H16B	109.5
C9A—C11A—H15A	109.5	H15B—C11B—H16B	109.5
C9A—C11A—H16A	109.5	C9B—C11B—H17B	109.5
H15A—C11A—H16A	109.5	H15B—C11B—H17B	109.5
C9A—C11A—H17A	109.5	H16B—C11B—H17B	109.5
H15A—C11A—H17A	109.5	O3B—C12B—O2B	124.8 (2)
H16A—C11A—H17A	109.5	O3B—C12B—C7B	118.5 (2)
O3A—C12A—O2A	124.1 (2)	O2B—C12B—C7B	116.5 (2)
O3A—C12A—C7A	118.9 (2)	H11C—O1C—H12C	104.8
O2A—C12A—C7A	117.0 (2)	H11D—O1D—H12D	105.8
C1B—N1B—H1B	106.2 (19)	H11E—O1E—H12E	105.0
C1B—N1B—H2B	109 (2)	H11F—O1F—H12F	104.5

N1A—C1A—C6A—N2A	136.8 (2)	N1B—C1B—C6B—N2B	130.9 (2)
C1A—C6A—N2A—C7A	174.61 (19)	C1B—C6B—N2B—C7B	−174.5 (2)
C6A—N2A—C7A—C12A	49.9 (3)	C6B—N2B—C7B—C12B	50.4 (3)
N2A—C7A—C12A—O2A	47.9 (3)	N2B—C7B—C12B—O2B	49.3 (3)
N1A—C1A—C2A—C3A	55.6 (3)	N1B—C1B—C2B—C3B	54.2 (4)
N1A—C1A—C2A—C4A	−179.0 (2)	N1B—C1B—C2B—C4B	−178.7 (3)
C1A—C2A—C4A—C5A	170.1 (3)	C1B—C2B—C4B—C5B	166.9 (4)
N2A—C7A—C8A—C9A	−66.9 (3)	N2B—C7B—C8B—C9B	−63.6 (3)
C7A—C8A—C9A—C10A	163.1 (2)	C7B—C8B—C9B—C10B	174.5 (2)
C7A—C8A—C9A—C11A	−73.1 (3)	C7B—C8B—C9B—C11B	−63.3 (3)
C6A—C1A—C2A—C3A	−63.9 (3)	C6B—C1B—C2B—C3B	−65.4 (3)
C6A—C1A—C2A—C4A	61.5 (3)	C6B—C1B—C2B—C4B	61.6 (3)
C3A—C2A—C4A—C5A	−63.6 (3)	C3B—C2B—C4B—C5B	−66.4 (4)
C7A—N2A—C6A—O1A	−4.2 (4)	C7B—N2B—C6B—O1B	4.3 (4)
N1A—C1A—C6A—O1A	−44.3 (3)	N1B—C1B—C6B—O1B	−47.9 (3)
C2A—C1A—C6A—O1A	77.4 (3)	C2B—C1B—C6B—O1B	74.2 (3)
C2A—C1A—C6A—N2A	−101.4 (2)	C2B—C1B—C6B—N2B	−107.0 (3)
C6A—N2A—C7A—C8A	−77.9 (3)	C6B—N2B—C7B—C8B	−77.1 (3)
C12A—C7A—C8A—C9A	168.46 (19)	C12B—C7B—C8B—C9B	170.8 (2)
N2A—C7A—C12A—O3A	−133.1 (2)	N2B—C7B—C12B—O3B	−134.6 (2)
C8A—C7A—C12A—O3A	−7.5 (3)	C8B—C7B—C12B—O3B	−7.5 (3)
C8A—C7A—C12A—O2A	173.5 (2)	C8B—C7B—C12B—O2B	176.4 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1A—H1A···O1C	0.96 (2)	2.00 (3)	2.927 (4)	161 (3)
N1A—H1A···O1Eⁱ	0.96 (2)	1.96 (3)	2.655 (11)	128 (2)
N1A—H2A···O3Bⁱ	0.99 (3)	1.73 (3)	2.717 (3)	171 (3)
N1A—H3A···O2Bⁱⁱ	0.92 (3)	2.38 (3)	3.117 (3)	136 (2)
N2A—H4A···O3Aⁱⁱⁱ	0.84 (3)	2.15 (3)	2.838 (3)	138 (2)
C1A—H11A···O1Aⁱⁱⁱ	0.93 (3)	2.45 (3)	3.343 (3)	160 (2)
C7A—H71A···O3Aⁱⁱⁱ	1.01 (3)	2.50 (3)	3.167 (3)	123 (2)
N1B—H1B···O1C	0.95 (3)	1.98 (3)	2.930 (4)	171 (3)
N1B—H1B···O1F	0.95 (3)	2.13 (3)	2.914 (13)	139 (3)
N1B—H2B···O3Aⁱⁱⁱ	0.95 (3)	1.88 (3)	2.800 (3)	163 (3)
N1B—H2B···O2Aⁱⁱⁱ	0.95 (3)	2.24 (3)	2.902 (3)	126 (3)
N1B—H3B···O2A	0.96 (3)	1.77 (3)	2.714 (3)	167 (3)
N2B—H4B···O3Bⁱⁱⁱ	0.82 (3)	2.30 (3)	2.992 (3)	142 (3)
C1B—H11B···O1Bⁱⁱⁱ	0.96 (3)	2.43 (3)	3.355 (3)	162 (3)
O1C—H11C···O2B	0.85 (1)	1.93 (1)	2.779 (3)	169 (4)
O1C—H12C···O1Dⁱⁱⁱ	0.85 (1)	1.87 (3)	2.638 (7)	149 (5)
O1D—H11D···O2A	0.85 (1)	2.19 (3)	2.993 (4)	159 (7)
O1D—H12D···O2B	0.85 (1)	2.20 (2)	3.024 (4)	164 (6)
O1E—H11E···O2B	0.85 (1)	1.74 (2)	2.589 (10)	176 (9)
O1E—H12E···O1Fⁱⁱ	0.85 (1)	2.13 (6)	2.733 (16)	127 (9)
O1F—H11F···O2B	0.85 (1)	2.09 (4)	2.896 (13)	156 (8)
O1F—H12F···O3Bⁱⁱⁱ	0.85 (1)	2.42 (6)	3.155 (13)	145 (8)

Symmetry codes: (i) −x+1/2, y+1/2, −z+1; (ii) −x+1/2, y−1/2, −z+1; (iii) x, y+1, z.

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Text
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Text
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page