Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802004506/bt6124sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536802004506/bt6124Isup2.hkl |
CCDC reference: 183797
Data collection: IPDS Program Package (Stoe & Cie, 1998); cell refinement: IPDS Program Package; data reduction: IPDS Program Package; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in SHELXTL (Bruker, 1998); software used to prepare material for publication: CIFTAB in SHELXL97.
C16H24N4O4 | Z = 4 |
Mr = 336.39 | F(000) = 720 |
Triclinic, P1 | Dx = 1.349 Mg m−3 |
a = 8.5284 (6) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 12.2178 (9) Å | Cell parameters from 8000 reflections |
c = 16.2102 (12) Å | θ = 10.5–27° |
α = 91.481 (9)° | µ = 0.10 mm−1 |
β = 101.269 (8)° | T = 170 K |
γ = 90.518 (8)° | Needle, colourless |
V = 1655.8 (2) Å3 | 0.4 × 0.1 × 0.08 mm |
Stoe Imaging Plate Diffraction System diffractometer | 5552 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.033 |
Graphite monochromator | θmax = 28.1°, θmin = 2.5° |
φ scans | h = −11→11 |
15745 measured reflections | k = −16→16 |
7846 independent reflections | l = −21→20 |
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)] = 0.049 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.140 | w = 1/[σ2(Fo2) + (0.0822P)2 + 0.1459P] where P = (Fo2 + 2Fc2)/3 |
S = 1.02 | (Δ/σ)max = 0.001 |
7846 reflections | Δρmax = 0.26 e Å−3 |
442 parameters | Δρmin = −0.31 e Å−3 |
0 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.035 (2) |
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. |
x | y | z | Uiso*/Ueq | ||
N1 | 0.77510 (18) | 0.95707 (11) | 0.32436 (10) | 0.0285 (3) | |
C2 | 0.9282 (2) | 0.93997 (15) | 0.36440 (12) | 0.0325 (4) | |
N3 | 0.97635 (17) | 0.83147 (12) | 0.38259 (10) | 0.0301 (3) | |
C4 | 0.8845 (2) | 0.74016 (13) | 0.35502 (10) | 0.0248 (3) | |
C5 | 0.72079 (19) | 0.76051 (12) | 0.30527 (10) | 0.0230 (3) | |
H5 | 0.6450 | 0.7032 | 0.3178 | 0.028* | |
C6 | 0.64595 (19) | 0.87469 (13) | 0.31050 (10) | 0.0248 (3) | |
C11 | 0.7314 (3) | 1.07289 (15) | 0.31682 (14) | 0.0425 (5) | |
H11A | 0.7629 | 1.1105 | 0.3718 | 0.064* | |
H11B | 0.6155 | 1.0784 | 0.2974 | 0.064* | |
H11C | 0.7866 | 1.1071 | 0.2762 | 0.064* | |
O12 | 1.0243 (2) | 1.01508 (13) | 0.38405 (12) | 0.0524 (4) | |
C13 | 1.1406 (2) | 0.81515 (19) | 0.42869 (15) | 0.0445 (5) | |
H13A | 1.1379 | 0.7900 | 0.4853 | 0.067* | |
H13B | 1.2008 | 0.8845 | 0.4328 | 0.067* | |
H13C | 1.1927 | 0.7601 | 0.3986 | 0.067* | |
O14 | 0.93359 (16) | 0.64769 (10) | 0.37032 (8) | 0.0317 (3) | |
C16 | 0.5336 (2) | 0.88878 (16) | 0.37258 (11) | 0.0319 (4) | |
H16A | 0.4867 | 0.9627 | 0.3669 | 0.038* | |
H16B | 0.4450 | 0.8344 | 0.3581 | 0.038* | |
C17 | 0.6175 (3) | 0.8745 (2) | 0.46369 (12) | 0.0436 (5) | |
H17A | 0.5405 | 0.8848 | 0.5008 | 0.065* | |
H17B | 0.7042 | 0.9289 | 0.4787 | 0.065* | |
H17C | 0.6616 | 0.8008 | 0.4701 | 0.065* | |
N21 | 0.57855 (18) | 0.94924 (11) | 0.15695 (9) | 0.0276 (3) | |
C22 | 0.7057 (2) | 0.97327 (13) | 0.12154 (11) | 0.0286 (3) | |
N23 | 0.83927 (17) | 0.90342 (11) | 0.13592 (9) | 0.0263 (3) | |
C24 | 0.8491 (2) | 0.80843 (13) | 0.17937 (10) | 0.0258 (3) | |
C25 | 0.70066 (19) | 0.77042 (12) | 0.20801 (10) | 0.0229 (3) | |
H25 | 0.6539 | 0.7022 | 0.1771 | 0.027* | |
C26 | 0.57252 (19) | 0.85783 (13) | 0.21209 (10) | 0.0241 (3) | |
C31 | 0.4471 (2) | 1.02782 (16) | 0.14173 (14) | 0.0391 (4) | |
H31A | 0.4913 | 1.1026 | 0.1472 | 0.059* | |
H31B | 0.3785 | 1.0180 | 0.1830 | 0.059* | |
H31C | 0.3841 | 1.0153 | 0.0849 | 0.059* | |
O32 | 0.70962 (18) | 1.05396 (11) | 0.07859 (9) | 0.0399 (3) | |
C33 | 0.9797 (2) | 0.93739 (16) | 0.10263 (13) | 0.0365 (4) | |
H33A | 1.0570 | 0.9749 | 0.1473 | 0.055* | |
H33B | 0.9467 | 0.9873 | 0.0562 | 0.055* | |
H33C | 1.0291 | 0.8727 | 0.0821 | 0.055* | |
O34 | 0.97229 (16) | 0.75531 (11) | 0.19305 (9) | 0.0352 (3) | |
C36 | 0.4054 (2) | 0.80402 (14) | 0.19543 (11) | 0.0278 (3) | |
H36A | 0.4073 | 0.7397 | 0.2315 | 0.033* | |
H36B | 0.3284 | 0.8567 | 0.2115 | 0.033* | |
C37 | 0.3476 (2) | 0.76733 (16) | 0.10347 (12) | 0.0339 (4) | |
H37A | 0.2408 | 0.7340 | 0.0966 | 0.051* | |
H37B | 0.4218 | 0.7136 | 0.0875 | 0.051* | |
H37C | 0.3433 | 0.8309 | 0.0675 | 0.051* | |
N41 | 1.06470 (17) | 0.33577 (11) | 0.12378 (9) | 0.0258 (3) | |
C42 | 1.1967 (2) | 0.30735 (14) | 0.09367 (10) | 0.0272 (3) | |
N43 | 1.33438 (17) | 0.37560 (11) | 0.11495 (9) | 0.0266 (3) | |
C44 | 1.3473 (2) | 0.46994 (13) | 0.16361 (10) | 0.0249 (3) | |
C45 | 1.19840 (19) | 0.50924 (12) | 0.19143 (10) | 0.0231 (3) | |
H45 | 1.1610 | 0.5801 | 0.1654 | 0.028* | |
C46 | 1.06037 (18) | 0.42492 (12) | 0.18442 (10) | 0.0220 (3) | |
C51 | 0.9266 (2) | 0.26086 (16) | 0.10311 (13) | 0.0377 (4) | |
H51A | 0.8466 | 0.2914 | 0.0582 | 0.057* | |
H51B | 0.8799 | 0.2513 | 0.1531 | 0.057* | |
H51C | 0.9611 | 0.1898 | 0.0842 | 0.057* | |
O52 | 1.20133 (18) | 0.22605 (12) | 0.04861 (9) | 0.0414 (3) | |
C53 | 1.4775 (2) | 0.33980 (17) | 0.08491 (14) | 0.0399 (4) | |
H53A | 1.5232 | 0.4014 | 0.0596 | 0.060* | |
H53B | 1.4486 | 0.2803 | 0.0428 | 0.060* | |
H53C | 1.5565 | 0.3137 | 0.1323 | 0.060* | |
O54 | 1.47316 (16) | 0.52123 (11) | 0.18192 (9) | 0.0365 (3) | |
C56 | 0.8985 (2) | 0.48275 (14) | 0.16759 (10) | 0.0268 (3) | |
H56A | 0.8144 | 0.4306 | 0.1765 | 0.032* | |
H56B | 0.9021 | 0.5443 | 0.2089 | 0.032* | |
C57 | 0.8531 (2) | 0.52681 (17) | 0.07899 (12) | 0.0362 (4) | |
H57A | 0.7491 | 0.5625 | 0.0724 | 0.054* | |
H57B | 0.8466 | 0.4662 | 0.0376 | 0.054* | |
H57C | 0.9344 | 0.5800 | 0.0700 | 0.054* | |
N61 | 1.24209 (17) | 0.31417 (11) | 0.29264 (9) | 0.0270 (3) | |
C62 | 1.3964 (2) | 0.32677 (16) | 0.33367 (12) | 0.0330 (4) | |
N63 | 1.45316 (18) | 0.43230 (14) | 0.36280 (10) | 0.0333 (3) | |
C64 | 1.3696 (2) | 0.52663 (15) | 0.34441 (10) | 0.0284 (3) | |
C65 | 1.20846 (18) | 0.51303 (12) | 0.28874 (10) | 0.0222 (3) | |
H65 | 1.1359 | 0.5709 | 0.3037 | 0.027* | |
C66 | 1.12193 (18) | 0.40039 (12) | 0.28203 (10) | 0.0224 (3) | |
C71 | 1.1882 (3) | 0.19960 (15) | 0.27811 (14) | 0.0393 (4) | |
H71A | 1.2370 | 0.1661 | 0.2338 | 0.059* | |
H71B | 1.0715 | 0.1967 | 0.2606 | 0.059* | |
H71C | 1.2201 | 0.1595 | 0.3302 | 0.059* | |
O72 | 1.4870 (2) | 0.24925 (14) | 0.34606 (12) | 0.0526 (4) | |
C73 | 1.6170 (2) | 0.4408 (2) | 0.41237 (15) | 0.0507 (6) | |
H73A | 1.6585 | 0.5154 | 0.4098 | 0.076* | |
H73B | 1.6853 | 0.3889 | 0.3893 | 0.076* | |
H73C | 1.6164 | 0.4236 | 0.4710 | 0.076* | |
O74 | 1.42366 (17) | 0.61632 (12) | 0.37140 (9) | 0.0384 (3) | |
C76 | 0.9985 (2) | 0.38518 (14) | 0.33795 (11) | 0.0284 (3) | |
H76A | 0.9201 | 0.4450 | 0.3282 | 0.034* | |
H76B | 0.9400 | 0.3150 | 0.3222 | 0.034* | |
C77 | 1.0757 (3) | 0.3852 (2) | 0.43045 (13) | 0.0502 (6) | |
H77A | 0.9930 | 0.3758 | 0.4641 | 0.075* | |
H77B | 1.1327 | 0.4549 | 0.4465 | 0.075* | |
H77C | 1.1514 | 0.3248 | 0.4406 | 0.075* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0290 (7) | 0.0208 (6) | 0.0352 (7) | −0.0013 (5) | 0.0052 (6) | −0.0006 (5) |
C2 | 0.0298 (9) | 0.0291 (8) | 0.0379 (9) | −0.0050 (7) | 0.0055 (7) | 0.0009 (7) |
N3 | 0.0222 (7) | 0.0309 (7) | 0.0365 (8) | −0.0001 (5) | 0.0040 (6) | 0.0009 (6) |
C4 | 0.0248 (8) | 0.0258 (7) | 0.0259 (7) | 0.0027 (6) | 0.0097 (6) | 0.0044 (6) |
C5 | 0.0221 (7) | 0.0209 (7) | 0.0274 (7) | 0.0007 (5) | 0.0077 (6) | 0.0028 (6) |
C6 | 0.0240 (8) | 0.0221 (7) | 0.0292 (8) | 0.0010 (6) | 0.0071 (6) | −0.0002 (6) |
C11 | 0.0516 (12) | 0.0216 (8) | 0.0503 (12) | 0.0024 (8) | 0.0005 (9) | −0.0030 (8) |
O12 | 0.0408 (9) | 0.0387 (8) | 0.0716 (11) | −0.0166 (6) | −0.0034 (7) | 0.0038 (7) |
C13 | 0.0234 (9) | 0.0510 (12) | 0.0554 (12) | 0.0003 (8) | −0.0018 (8) | 0.0028 (10) |
O14 | 0.0331 (7) | 0.0293 (6) | 0.0333 (6) | 0.0090 (5) | 0.0071 (5) | 0.0059 (5) |
C16 | 0.0292 (9) | 0.0361 (9) | 0.0324 (9) | 0.0058 (7) | 0.0110 (7) | −0.0005 (7) |
C17 | 0.0430 (11) | 0.0604 (13) | 0.0302 (9) | 0.0083 (10) | 0.0132 (8) | 0.0020 (9) |
N21 | 0.0275 (7) | 0.0223 (6) | 0.0336 (7) | 0.0032 (5) | 0.0062 (6) | 0.0066 (5) |
C22 | 0.0323 (9) | 0.0220 (7) | 0.0301 (8) | −0.0032 (6) | 0.0023 (7) | 0.0050 (6) |
N23 | 0.0277 (7) | 0.0241 (6) | 0.0291 (7) | −0.0024 (5) | 0.0106 (6) | 0.0040 (5) |
C24 | 0.0277 (8) | 0.0260 (7) | 0.0248 (7) | 0.0003 (6) | 0.0078 (6) | 0.0015 (6) |
C25 | 0.0241 (8) | 0.0193 (7) | 0.0262 (7) | 0.0004 (6) | 0.0071 (6) | 0.0022 (5) |
C26 | 0.0226 (7) | 0.0219 (7) | 0.0282 (8) | 0.0007 (6) | 0.0060 (6) | 0.0035 (6) |
C31 | 0.0350 (10) | 0.0290 (9) | 0.0533 (11) | 0.0093 (7) | 0.0073 (8) | 0.0113 (8) |
O32 | 0.0428 (8) | 0.0300 (7) | 0.0463 (8) | −0.0047 (6) | 0.0059 (6) | 0.0175 (6) |
C33 | 0.0351 (10) | 0.0351 (9) | 0.0440 (10) | −0.0061 (7) | 0.0189 (8) | 0.0061 (8) |
O34 | 0.0295 (7) | 0.0382 (7) | 0.0418 (7) | 0.0092 (5) | 0.0153 (5) | 0.0080 (6) |
C36 | 0.0239 (8) | 0.0286 (8) | 0.0311 (8) | 0.0001 (6) | 0.0058 (6) | 0.0045 (6) |
C37 | 0.0316 (9) | 0.0368 (9) | 0.0316 (9) | −0.0053 (7) | 0.0019 (7) | 0.0043 (7) |
N41 | 0.0228 (7) | 0.0247 (6) | 0.0289 (7) | −0.0039 (5) | 0.0037 (5) | −0.0051 (5) |
C42 | 0.0273 (8) | 0.0258 (8) | 0.0278 (8) | 0.0019 (6) | 0.0041 (6) | −0.0021 (6) |
N43 | 0.0240 (7) | 0.0277 (7) | 0.0293 (7) | 0.0012 (5) | 0.0086 (5) | −0.0006 (5) |
C44 | 0.0235 (8) | 0.0253 (7) | 0.0265 (7) | −0.0014 (6) | 0.0063 (6) | 0.0035 (6) |
C45 | 0.0222 (7) | 0.0202 (7) | 0.0269 (7) | −0.0022 (5) | 0.0048 (6) | 0.0023 (6) |
C46 | 0.0194 (7) | 0.0209 (7) | 0.0258 (7) | −0.0025 (5) | 0.0049 (6) | −0.0003 (5) |
C51 | 0.0318 (9) | 0.0342 (9) | 0.0457 (10) | −0.0116 (7) | 0.0062 (8) | −0.0114 (8) |
O52 | 0.0407 (8) | 0.0367 (7) | 0.0469 (8) | 0.0008 (6) | 0.0111 (6) | −0.0169 (6) |
C53 | 0.0309 (9) | 0.0424 (10) | 0.0508 (11) | 0.0036 (8) | 0.0198 (8) | −0.0034 (9) |
O54 | 0.0254 (6) | 0.0389 (7) | 0.0470 (8) | −0.0095 (5) | 0.0125 (6) | −0.0030 (6) |
C56 | 0.0218 (8) | 0.0301 (8) | 0.0281 (8) | 0.0015 (6) | 0.0036 (6) | 0.0008 (6) |
C57 | 0.0306 (9) | 0.0447 (10) | 0.0314 (9) | 0.0089 (8) | 0.0008 (7) | 0.0039 (7) |
N61 | 0.0279 (7) | 0.0221 (6) | 0.0318 (7) | 0.0050 (5) | 0.0072 (6) | 0.0037 (5) |
C62 | 0.0285 (9) | 0.0376 (9) | 0.0346 (9) | 0.0097 (7) | 0.0093 (7) | 0.0073 (7) |
N63 | 0.0211 (7) | 0.0428 (9) | 0.0343 (8) | 0.0015 (6) | 0.0009 (6) | 0.0045 (6) |
C64 | 0.0229 (8) | 0.0368 (9) | 0.0258 (8) | −0.0048 (6) | 0.0065 (6) | −0.0028 (6) |
C65 | 0.0197 (7) | 0.0215 (7) | 0.0257 (7) | −0.0013 (5) | 0.0053 (6) | −0.0004 (5) |
C66 | 0.0204 (7) | 0.0203 (7) | 0.0271 (7) | 0.0005 (5) | 0.0059 (6) | 0.0026 (6) |
C71 | 0.0473 (12) | 0.0226 (8) | 0.0497 (11) | 0.0027 (7) | 0.0126 (9) | 0.0044 (7) |
O72 | 0.0409 (9) | 0.0488 (9) | 0.0679 (11) | 0.0238 (7) | 0.0075 (7) | 0.0099 (8) |
C73 | 0.0222 (9) | 0.0766 (16) | 0.0496 (12) | 0.0009 (10) | −0.0032 (8) | 0.0083 (11) |
O74 | 0.0321 (7) | 0.0418 (7) | 0.0400 (7) | −0.0129 (6) | 0.0061 (6) | −0.0094 (6) |
C76 | 0.0271 (8) | 0.0298 (8) | 0.0305 (8) | −0.0015 (6) | 0.0107 (6) | 0.0037 (6) |
C77 | 0.0408 (12) | 0.0834 (17) | 0.0306 (10) | 0.0144 (11) | 0.0150 (8) | 0.0153 (10) |
N1—C2 | 1.360 (2) | N41—C42 | 1.356 (2) |
N1—C6 | 1.466 (2) | N41—C46 | 1.454 (2) |
N1—C11 | 1.469 (2) | N41—C51 | 1.465 (2) |
C2—O12 | 1.219 (2) | C42—O52 | 1.223 (2) |
C2—N3 | 1.413 (2) | C42—N43 | 1.415 (2) |
N3—C4 | 1.371 (2) | N43—C44 | 1.371 (2) |
N3—C13 | 1.471 (2) | N43—C53 | 1.466 (2) |
C4—O14 | 1.223 (2) | C44—O54 | 1.220 (2) |
C4—C5 | 1.496 (2) | C44—C45 | 1.506 (2) |
C5—C6 | 1.547 (2) | C45—C46 | 1.543 (2) |
C5—C25 | 1.560 (2) | C45—C65 | 1.562 (2) |
C5—H5 | 1.0000 | C45—H45 | 1.0000 |
C6—C16 | 1.527 (2) | C46—C56 | 1.536 (2) |
C6—C26 | 1.603 (2) | C46—C66 | 1.604 (2) |
C11—H11A | 0.9800 | C51—H51A | 0.9800 |
C11—H11B | 0.9800 | C51—H51B | 0.9800 |
C11—H11C | 0.9800 | C51—H51C | 0.9800 |
C13—H13A | 0.9800 | C53—H53A | 0.9800 |
C13—H13B | 0.9800 | C53—H53B | 0.9800 |
C13—H13C | 0.9800 | C53—H53C | 0.9800 |
C16—C17 | 1.525 (3) | C56—C57 | 1.526 (2) |
C16—H16A | 0.9900 | C56—H56A | 0.9900 |
C16—H16B | 0.9900 | C56—H56B | 0.9900 |
C17—H17A | 0.9800 | C57—H57A | 0.9800 |
C17—H17B | 0.9800 | C57—H57B | 0.9800 |
C17—H17C | 0.9800 | C57—H57C | 0.9800 |
N21—C22 | 1.356 (2) | N61—C62 | 1.359 (2) |
N21—C26 | 1.455 (2) | N61—C66 | 1.4662 (19) |
N21—C31 | 1.470 (2) | N61—C71 | 1.468 (2) |
C22—O32 | 1.225 (2) | C62—O72 | 1.223 (2) |
C22—N23 | 1.416 (2) | C62—N63 | 1.410 (3) |
N23—C24 | 1.368 (2) | N63—C64 | 1.369 (2) |
N23—C33 | 1.467 (2) | N63—C73 | 1.471 (2) |
C24—O34 | 1.226 (2) | C64—O74 | 1.222 (2) |
C24—C25 | 1.505 (2) | C64—C65 | 1.495 (2) |
C25—C26 | 1.544 (2) | C65—C66 | 1.547 (2) |
C25—H25 | 1.0000 | C65—H65 | 1.0000 |
C26—C36 | 1.536 (2) | C66—C76 | 1.530 (2) |
C31—H31A | 0.9800 | C71—H71A | 0.9800 |
C31—H31B | 0.9800 | C71—H71B | 0.9800 |
C31—H31C | 0.9800 | C71—H71C | 0.9800 |
C33—H33A | 0.9800 | C73—H73A | 0.9800 |
C33—H33B | 0.9800 | C73—H73B | 0.9800 |
C33—H33C | 0.9800 | C73—H73C | 0.9800 |
C36—C37 | 1.530 (2) | C76—C77 | 1.515 (3) |
C36—H36A | 0.9900 | C76—H76A | 0.9900 |
C36—H36B | 0.9900 | C76—H76B | 0.9900 |
C37—H37A | 0.9800 | C77—H77A | 0.9800 |
C37—H37B | 0.9800 | C77—H77B | 0.9800 |
C37—H37C | 0.9800 | C77—H77C | 0.9800 |
C2—N1—C6 | 125.26 (14) | C42—N41—C46 | 124.19 (14) |
C2—N1—C11 | 114.40 (15) | C42—N41—C51 | 116.67 (14) |
C6—N1—C11 | 118.08 (15) | C46—N41—C51 | 118.46 (14) |
O12—C2—N1 | 121.95 (18) | O52—C42—N41 | 122.91 (16) |
O12—C2—N3 | 119.52 (18) | O52—C42—N43 | 118.81 (16) |
N1—C2—N3 | 118.53 (15) | N41—C42—N43 | 118.28 (14) |
C4—N3—C2 | 124.40 (15) | C44—N43—C42 | 125.75 (14) |
C4—N3—C13 | 117.78 (15) | C44—N43—C53 | 117.25 (15) |
C2—N3—C13 | 117.65 (16) | C42—N43—C53 | 116.95 (14) |
O14—C4—N3 | 121.92 (16) | O54—C44—N43 | 121.32 (15) |
O14—C4—C5 | 122.10 (16) | O54—C44—C45 | 121.43 (15) |
N3—C4—C5 | 115.98 (14) | N43—C44—C45 | 117.23 (14) |
C4—C5—C6 | 119.52 (14) | C44—C45—C46 | 116.34 (13) |
C4—C5—C25 | 118.08 (13) | C44—C45—C65 | 114.83 (13) |
C6—C5—C25 | 89.75 (11) | C46—C45—C65 | 88.10 (11) |
C4—C5—H5 | 109.3 | C44—C45—H45 | 111.9 |
C6—C5—H5 | 109.3 | C46—C45—H45 | 111.9 |
C25—C5—H5 | 109.3 | C65—C45—H45 | 111.9 |
N1—C6—C16 | 112.34 (14) | N41—C46—C56 | 111.52 (13) |
N1—C6—C5 | 108.30 (13) | N41—C46—C45 | 114.34 (13) |
C16—C6—C5 | 116.52 (13) | C56—C46—C45 | 110.35 (13) |
N1—C6—C26 | 110.80 (13) | N41—C46—C66 | 117.54 (13) |
C16—C6—C26 | 119.49 (14) | C56—C46—C66 | 112.72 (12) |
C5—C6—C26 | 86.61 (11) | C45—C46—C66 | 88.36 (11) |
N1—C11—H11A | 109.5 | N41—C51—H51A | 109.5 |
N1—C11—H11B | 109.5 | N41—C51—H51B | 109.5 |
H11A—C11—H11B | 109.5 | H51A—C51—H51B | 109.5 |
N1—C11—H11C | 109.5 | N41—C51—H51C | 109.5 |
H11A—C11—H11C | 109.5 | H51A—C51—H51C | 109.5 |
H11B—C11—H11C | 109.5 | H51B—C51—H51C | 109.5 |
N3—C13—H13A | 109.5 | N43—C53—H53A | 109.5 |
N3—C13—H13B | 109.5 | N43—C53—H53B | 109.5 |
H13A—C13—H13B | 109.5 | H53A—C53—H53B | 109.5 |
N3—C13—H13C | 109.5 | N43—C53—H53C | 109.5 |
H13A—C13—H13C | 109.5 | H53A—C53—H53C | 109.5 |
H13B—C13—H13C | 109.5 | H53B—C53—H53C | 109.5 |
C17—C16—C6 | 112.79 (15) | C57—C56—C46 | 113.59 (14) |
C17—C16—H16A | 109.0 | C57—C56—H56A | 108.8 |
C6—C16—H16A | 109.0 | C46—C56—H56A | 108.8 |
C17—C16—H16B | 109.0 | C57—C56—H56B | 108.8 |
C6—C16—H16B | 109.0 | C46—C56—H56B | 108.8 |
H16A—C16—H16B | 107.8 | H56A—C56—H56B | 107.7 |
C16—C17—H17A | 109.5 | C56—C57—H57A | 109.5 |
C16—C17—H17B | 109.5 | C56—C57—H57B | 109.5 |
H17A—C17—H17B | 109.5 | H57A—C57—H57B | 109.5 |
C16—C17—H17C | 109.5 | C56—C57—H57C | 109.5 |
H17A—C17—H17C | 109.5 | H57A—C57—H57C | 109.5 |
H17B—C17—H17C | 109.5 | H57B—C57—H57C | 109.5 |
C22—N21—C26 | 124.03 (14) | C62—N61—C66 | 125.32 (14) |
C22—N21—C31 | 115.42 (14) | C62—N61—C71 | 114.09 (15) |
C26—N21—C31 | 120.38 (14) | C66—N61—C71 | 118.72 (15) |
O32—C22—N21 | 122.24 (17) | O72—C62—N61 | 121.88 (19) |
O32—C22—N23 | 119.11 (16) | O72—C62—N63 | 119.25 (19) |
N21—C22—N23 | 118.64 (14) | N61—C62—N63 | 118.86 (15) |
C24—N23—C22 | 125.51 (14) | C64—N63—C62 | 124.51 (15) |
C24—N23—C33 | 117.58 (15) | C64—N63—C73 | 118.47 (18) |
C22—N23—C33 | 116.90 (14) | C62—N63—C73 | 116.93 (17) |
O34—C24—N23 | 121.61 (15) | O74—C64—N63 | 122.13 (17) |
O34—C24—C25 | 121.32 (15) | O74—C64—C65 | 122.09 (16) |
N23—C24—C25 | 117.06 (14) | N63—C64—C65 | 115.78 (15) |
C24—C25—C26 | 116.29 (13) | C64—C65—C66 | 119.28 (14) |
C24—C25—C5 | 114.27 (13) | C64—C65—C45 | 118.15 (13) |
C26—C25—C5 | 88.20 (11) | C66—C65—C45 | 89.72 (11) |
C24—C25—H25 | 112.0 | C64—C65—H65 | 109.4 |
C26—C25—H25 | 112.0 | C66—C65—H65 | 109.4 |
C5—C25—H25 | 112.0 | C45—C65—H65 | 109.4 |
N21—C26—C36 | 111.11 (13) | N61—C66—C76 | 112.42 (13) |
N21—C26—C25 | 114.15 (13) | N61—C66—C65 | 108.79 (13) |
C36—C26—C25 | 110.07 (13) | C76—C66—C65 | 116.59 (13) |
N21—C26—C6 | 118.64 (13) | N61—C66—C46 | 111.02 (12) |
C36—C26—C6 | 112.60 (13) | C76—C66—C46 | 118.80 (13) |
C25—C26—C6 | 88.27 (11) | C65—C66—C46 | 86.48 (11) |
N21—C31—H31A | 109.5 | N61—C71—H71A | 109.5 |
N21—C31—H31B | 109.5 | N61—C71—H71B | 109.5 |
H31A—C31—H31B | 109.5 | H71A—C71—H71B | 109.5 |
N21—C31—H31C | 109.5 | N61—C71—H71C | 109.5 |
H31A—C31—H31C | 109.5 | H71A—C71—H71C | 109.5 |
H31B—C31—H31C | 109.5 | H71B—C71—H71C | 109.5 |
N23—C33—H33A | 109.5 | N63—C73—H73A | 109.5 |
N23—C33—H33B | 109.5 | N63—C73—H73B | 109.5 |
H33A—C33—H33B | 109.5 | H73A—C73—H73B | 109.5 |
N23—C33—H33C | 109.5 | N63—C73—H73C | 109.5 |
H33A—C33—H33C | 109.5 | H73A—C73—H73C | 109.5 |
H33B—C33—H33C | 109.5 | H73B—C73—H73C | 109.5 |
C37—C36—C26 | 113.08 (14) | C77—C76—C66 | 111.94 (15) |
C37—C36—H36A | 109.0 | C77—C76—H76A | 109.2 |
C26—C36—H36A | 109.0 | C66—C76—H76A | 109.2 |
C37—C36—H36B | 109.0 | C77—C76—H76B | 109.2 |
C26—C36—H36B | 109.0 | C66—C76—H76B | 109.2 |
H36A—C36—H36B | 107.8 | H76A—C76—H76B | 107.9 |
C36—C37—H37A | 109.5 | C76—C77—H77A | 109.5 |
C36—C37—H37B | 109.5 | C76—C77—H77B | 109.5 |
H37A—C37—H37B | 109.5 | H77A—C77—H77B | 109.5 |
C36—C37—H37C | 109.5 | C76—C77—H77C | 109.5 |
H37A—C37—H37C | 109.5 | H77A—C77—H77C | 109.5 |
H37B—C37—H37C | 109.5 | H77B—C77—H77C | 109.5 |
C6—N1—C2—O12 | −169.77 (18) | C46—N41—C42—O52 | 173.20 (16) |
C11—N1—C2—O12 | −7.3 (3) | C51—N41—C42—O52 | 2.9 (3) |
C6—N1—C2—N3 | 11.0 (3) | C46—N41—C42—N43 | −7.4 (2) |
C11—N1—C2—N3 | 173.42 (17) | C51—N41—C42—N43 | −177.70 (15) |
O12—C2—N3—C4 | −172.19 (18) | O52—C42—N43—C44 | 179.03 (17) |
N1—C2—N3—C4 | 7.1 (3) | N41—C42—N43—C44 | −0.4 (2) |
O12—C2—N3—C13 | 2.9 (3) | O52—C42—N43—C53 | −3.5 (2) |
N1—C2—N3—C13 | −177.80 (17) | N41—C42—N43—C53 | 177.06 (16) |
C2—N3—C4—O14 | 177.70 (16) | C42—N43—C44—O54 | 176.67 (16) |
C13—N3—C4—O14 | 2.6 (2) | C53—N43—C44—O54 | −0.8 (2) |
C2—N3—C4—C5 | −2.4 (2) | C42—N43—C44—C45 | −5.0 (2) |
C13—N3—C4—C5 | −177.47 (16) | C53—N43—C44—C45 | 177.51 (15) |
O14—C4—C5—C6 | 161.39 (15) | O54—C44—C45—C46 | −164.98 (15) |
N3—C4—C5—C6 | −18.5 (2) | N43—C44—C45—C46 | 16.7 (2) |
O14—C4—C5—C25 | −91.37 (19) | O54—C44—C45—C65 | −64.1 (2) |
N3—C4—C5—C25 | 88.71 (17) | N43—C44—C45—C65 | 117.55 (16) |
C2—N1—C6—C16 | 101.55 (19) | C42—N41—C46—C56 | 145.02 (16) |
C11—N1—C6—C16 | −60.3 (2) | C51—N41—C46—C56 | −44.8 (2) |
C2—N1—C6—C5 | −28.6 (2) | C42—N41—C46—C45 | 18.9 (2) |
C11—N1—C6—C5 | 169.55 (15) | C51—N41—C46—C45 | −170.88 (15) |
C2—N1—C6—C26 | −121.95 (17) | C42—N41—C46—C66 | −82.62 (19) |
C11—N1—C6—C26 | 76.17 (19) | C51—N41—C46—C66 | 87.56 (19) |
C4—C5—C6—N1 | 31.59 (19) | C44—C45—C46—N41 | −22.8 (2) |
C25—C5—C6—N1 | −90.98 (14) | C65—C45—C46—N41 | −139.70 (13) |
C4—C5—C6—C16 | −96.18 (18) | C44—C45—C46—C56 | −149.47 (14) |
C25—C5—C6—C16 | 141.25 (15) | C65—C45—C46—C56 | 93.62 (13) |
C4—C5—C6—C26 | 142.39 (14) | C44—C45—C46—C66 | 96.85 (14) |
C25—C5—C6—C26 | 19.82 (11) | C65—C45—C46—C66 | −20.05 (11) |
N1—C6—C16—C17 | −62.4 (2) | N41—C46—C56—C57 | −56.56 (19) |
C5—C6—C16—C17 | 63.3 (2) | C45—C46—C56—C57 | 71.67 (18) |
C26—C6—C16—C17 | 165.24 (16) | C66—C46—C56—C57 | 168.69 (14) |
C26—N21—C22—O32 | −176.47 (17) | C66—N61—C62—O72 | 174.02 (17) |
C31—N21—C22—O32 | −1.2 (3) | C71—N61—C62—O72 | 9.9 (3) |
C26—N21—C22—N23 | 2.6 (2) | C66—N61—C62—N63 | −5.9 (3) |
C31—N21—C22—N23 | 177.81 (16) | C71—N61—C62—N63 | −170.01 (16) |
O32—C22—N23—C24 | −177.07 (17) | O72—C62—N63—C64 | 172.08 (18) |
N21—C22—N23—C24 | 3.9 (3) | N61—C62—N63—C64 | −8.0 (3) |
O32—C22—N23—C33 | 4.2 (2) | O72—C62—N63—C73 | −4.4 (3) |
N21—C22—N23—C33 | −174.88 (16) | N61—C62—N63—C73 | 175.50 (17) |
C22—N23—C24—O34 | −176.01 (16) | C62—N63—C64—O74 | 179.75 (17) |
C33—N23—C24—O34 | 2.7 (2) | C73—N63—C64—O74 | −3.8 (3) |
C22—N23—C24—C25 | 5.4 (2) | C62—N63—C64—C65 | −0.6 (2) |
C33—N23—C24—C25 | −175.89 (15) | C73—N63—C64—C65 | 175.78 (16) |
O34—C24—C25—C26 | 161.92 (16) | O74—C64—C65—C66 | −158.63 (15) |
N23—C24—C25—C26 | −19.5 (2) | N63—C64—C65—C66 | 21.8 (2) |
O34—C24—C25—C5 | 61.3 (2) | O74—C64—C65—C45 | 94.29 (19) |
N23—C24—C25—C5 | −120.07 (15) | N63—C64—C65—C45 | −85.32 (18) |
C4—C5—C25—C24 | −26.20 (19) | C44—C45—C65—C64 | 26.0 (2) |
C6—C5—C25—C24 | 97.58 (14) | C46—C45—C65—C64 | 144.32 (14) |
C4—C5—C25—C26 | −144.36 (14) | C44—C45—C65—C66 | −97.47 (14) |
C6—C5—C25—C26 | −20.58 (12) | C46—C45—C65—C66 | 20.81 (11) |
C22—N21—C26—C36 | −141.73 (16) | C62—N61—C66—C76 | −106.50 (18) |
C31—N21—C26—C36 | 43.2 (2) | C71—N61—C66—C76 | 57.0 (2) |
C22—N21—C26—C25 | −16.5 (2) | C62—N61—C66—C65 | 24.2 (2) |
C31—N21—C26—C25 | 168.42 (16) | C71—N61—C66—C65 | −172.35 (14) |
C22—N21—C26—C6 | 85.4 (2) | C62—N61—C66—C46 | 117.70 (17) |
C31—N21—C26—C6 | −89.62 (19) | C71—N61—C66—C46 | −78.84 (18) |
C24—C25—C26—N21 | 24.3 (2) | C64—C65—C66—N61 | −31.56 (19) |
C5—C25—C26—N21 | 140.63 (14) | C45—C65—C66—N61 | 91.01 (13) |
C24—C25—C26—C36 | 150.04 (14) | C64—C65—C66—C76 | 96.82 (17) |
C5—C25—C26—C36 | −93.65 (14) | C45—C65—C66—C76 | −140.61 (14) |
C24—C25—C26—C6 | −96.48 (14) | C64—C65—C66—C46 | −142.58 (14) |
C5—C25—C26—C6 | 19.83 (11) | C45—C65—C66—C46 | −20.01 (11) |
N1—C6—C26—N21 | −28.48 (19) | N41—C46—C66—N61 | 28.26 (18) |
C16—C6—C26—N21 | 104.52 (17) | C56—C46—C66—N61 | 160.08 (13) |
C5—C6—C26—N21 | −136.77 (14) | C45—C46—C66—N61 | −88.50 (13) |
N1—C6—C26—C36 | −160.69 (13) | N41—C46—C66—C76 | −104.40 (16) |
C16—C6—C26—C36 | −27.69 (19) | C56—C46—C66—C76 | 27.42 (19) |
C5—C6—C26—C36 | 91.02 (14) | C45—C46—C66—C76 | 138.84 (14) |
N1—C6—C26—C25 | 88.25 (13) | N41—C46—C66—C65 | 137.04 (13) |
C16—C6—C26—C25 | −138.75 (15) | C56—C46—C66—C65 | −91.13 (13) |
C5—C6—C26—C25 | −20.04 (11) | C45—C46—C66—C65 | 20.29 (11) |
N21—C26—C36—C37 | 55.30 (18) | N61—C66—C76—C77 | 59.3 (2) |
C25—C26—C36—C37 | −72.13 (17) | C65—C66—C76—C77 | −67.3 (2) |
C6—C26—C36—C37 | −168.87 (14) | C46—C66—C76—C77 | −168.70 (16) |