Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802022225/ci6187sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536802022225/ci6187Isup2.hkl |
CCDC reference: 202989
Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 1999); software used to prepare material for publication: SHELXL97.
C5H12NO2+·ClO4− | Z = 8 |
Mr = 217.61 | F(000) = 912 |
Triclinic, P1 | Dx = 1.530 Mg m−3 Dm = 1.50 Mg m−3 Dm measured by flotation in a mixture of carbon tetrachloride and xylene |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71070 Å |
a = 10.3005 (6) Å | Cell parameters from 8152 reflections |
b = 13.0905 (8) Å | θ = 2.5–35.0° |
c = 14.6105 (9) Å | µ = 0.41 mm−1 |
α = 81.288 (2)° | T = 105 K |
β = 88.4473 (19)° | Plate, colorless |
γ = 75.9648 (19)° | 0.7 × 0.5 × 0.15 mm |
V = 1889.1 (2) Å3 |
Bruker SMART CCD diffractometer | 15604 independent reflections |
Radiation source: fine-focus sealed tube | 12138 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.020 |
Detector resolution: 8.33 pixels mm-1 | θmax = 35.1°, θmin = 1.4° |
ω scans | h = −16→16 |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | k = −21→21 |
Tmin = 0.76, Tmax = 0.94 | l = −23→23 |
35831 measured reflections |
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)] = 0.036 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.105 | H-atom parameters constrained |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0522P)2 + 0.6779P] where P = (Fo2 + 2Fc2)/3 |
15604 reflections | (Δ/σ)max = 0.002 |
485 parameters | Δρmax = 0.78 e Å−3 |
0 restraints | Δρmin = −0.54 e Å−3 |
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 | ||
Cl1 | 0.66873 (2) | 0.893149 (19) | 0.817212 (17) | 0.01552 (5) | |
O11 | 0.76072 (9) | 0.84376 (8) | 0.89155 (6) | 0.02528 (18) | |
O12 | 0.73948 (9) | 0.92487 (7) | 0.73479 (6) | 0.02430 (17) | |
O13 | 0.59270 (9) | 0.82024 (7) | 0.79486 (6) | 0.02318 (17) | |
O14 | 0.57590 (10) | 0.98674 (8) | 0.84367 (7) | 0.0308 (2) | |
Cl2 | 0.66344 (2) | 1.005117 (19) | 0.408864 (17) | 0.01586 (5) | |
O21 | 0.74562 (10) | 1.01445 (8) | 0.32912 (7) | 0.0295 (2) | |
O22 | 0.54022 (10) | 0.98222 (9) | 0.38580 (8) | 0.0347 (2) | |
O23 | 0.73582 (10) | 0.92302 (8) | 0.47938 (8) | 0.0338 (2) | |
O24 | 0.63256 (9) | 1.10502 (7) | 0.44624 (6) | 0.02397 (17) | |
Cl3 | 0.33296 (3) | 0.501837 (19) | 0.098497 (17) | 0.01683 (5) | |
O31 | 0.36925 (14) | 0.57718 (9) | 0.02752 (10) | 0.0550 (4) | |
O32 | 0.19527 (10) | 0.53822 (9) | 0.12232 (7) | 0.0322 (2) | |
O33 | 0.35737 (9) | 0.39904 (7) | 0.06830 (7) | 0.02488 (18) | |
O34 | 0.41625 (12) | 0.49198 (9) | 0.17972 (8) | 0.0414 (3) | |
Cl4 | 0.67119 (2) | 0.378808 (19) | 0.330192 (16) | 0.01480 (5) | |
O41 | 0.76844 (9) | 0.33058 (8) | 0.40217 (6) | 0.02494 (17) | |
O42 | 0.73619 (9) | 0.41280 (7) | 0.24598 (6) | 0.02373 (17) | |
O43 | 0.59667 (9) | 0.30374 (7) | 0.31094 (6) | 0.02147 (16) | |
O44 | 0.57803 (9) | 0.47075 (7) | 0.35974 (7) | 0.02634 (19) | |
O1A | 0.56652 (9) | 0.27665 (7) | 0.75114 (6) | 0.02522 (18) | |
O1B | 0.71043 (10) | 0.37587 (7) | 0.69865 (7) | 0.02738 (19) | |
H1B | 0.670 (2) | 0.4151 (16) | 0.7383 (14) | 0.041 (5)* | |
C11 | 0.65508 (11) | 0.29506 (8) | 0.69959 (7) | 0.01787 (19) | |
C12 | 0.71516 (10) | 0.22531 (8) | 0.62752 (7) | 0.01470 (17) | |
H12 | 0.6977 | 0.2688 | 0.5663 | 0.018* | |
N1 | 0.64138 (9) | 0.13933 (7) | 0.63272 (6) | 0.01647 (16) | |
H1A | 0.6742 | 0.0968 | 0.5912 | 0.025* | |
H1C | 0.5549 | 0.1684 | 0.6209 | 0.025* | |
H1D | 0.6511 | 0.1016 | 0.6892 | 0.025* | |
C13 | 0.86793 (11) | 0.18040 (9) | 0.63866 (8) | 0.01858 (19) | |
H13 | 0.9095 | 0.2405 | 0.6222 | 0.022* | |
C14 | 0.91084 (13) | 0.13110 (11) | 0.73832 (9) | 0.0260 (2) | |
H14A | 0.8770 | 0.1823 | 0.7791 | 0.039* | |
H14B | 1.0068 | 0.1106 | 0.7425 | 0.039* | |
H14C | 0.8757 | 0.0695 | 0.7559 | 0.039* | |
C15 | 0.91918 (12) | 0.10227 (11) | 0.56990 (10) | 0.0276 (3) | |
H15A | 0.8904 | 0.1361 | 0.5084 | 0.041* | |
H15B | 0.8841 | 0.0404 | 0.5858 | 0.041* | |
H15C | 1.0152 | 0.0815 | 0.5725 | 0.041* | |
O2A | 0.43593 (9) | 0.30578 (7) | 0.53587 (6) | 0.02418 (17) | |
O2B | 0.31609 (10) | 0.47309 (7) | 0.49077 (6) | 0.02417 (17) | |
H2B | 0.352 (2) | 0.4873 (15) | 0.5387 (14) | 0.038 (5)* | |
C21 | 0.36053 (11) | 0.37166 (8) | 0.48176 (7) | 0.01643 (18) | |
C22 | 0.30666 (10) | 0.34589 (8) | 0.39431 (7) | 0.01484 (17) | |
H22 | 0.3428 | 0.3849 | 0.3410 | 0.018* | |
N2 | 0.36225 (9) | 0.22939 (7) | 0.39283 (6) | 0.01628 (16) | |
H2A | 0.3328 | 0.2112 | 0.3424 | 0.024* | |
H2C | 0.3358 | 0.1924 | 0.4430 | 0.024* | |
H2D | 0.4512 | 0.2153 | 0.3922 | 0.024* | |
C23 | 0.15237 (10) | 0.37941 (9) | 0.38645 (7) | 0.01732 (18) | |
H23 | 0.1266 | 0.4574 | 0.3764 | 0.021* | |
C24 | 0.10323 (13) | 0.34255 (11) | 0.30178 (9) | 0.0254 (2) | |
H24A | 0.1482 | 0.3671 | 0.2475 | 0.038* | |
H24B | 0.0085 | 0.3713 | 0.2941 | 0.038* | |
H24C | 0.1223 | 0.2662 | 0.3107 | 0.038* | |
C25 | 0.08330 (12) | 0.34197 (12) | 0.47498 (9) | 0.0271 (2) | |
H25A | 0.1160 | 0.3662 | 0.5267 | 0.041* | |
H25B | 0.1022 | 0.2656 | 0.4852 | 0.041* | |
H25C | −0.0116 | 0.3707 | 0.4686 | 0.041* | |
O3A | 0.87416 (8) | 0.50013 (6) | 0.07502 (6) | 0.01906 (15) | |
O3B | 0.93978 (8) | 0.64102 (7) | −0.00291 (6) | 0.02141 (16) | |
H3B | 1.004 (2) | 0.5902 (16) | −0.0235 (14) | 0.042 (5)* | |
C31 | 0.86245 (10) | 0.59610 (8) | 0.05362 (7) | 0.01574 (17) | |
C32 | 0.75478 (10) | 0.67735 (8) | 0.09498 (7) | 0.01546 (17) | |
H32 | 0.7168 | 0.7358 | 0.0457 | 0.019* | |
N3 | 0.64675 (9) | 0.62359 (7) | 0.13106 (6) | 0.01619 (16) | |
H3A | 0.5823 | 0.6696 | 0.1557 | 0.024* | |
H3C | 0.6809 | 0.5684 | 0.1741 | 0.024* | |
H3D | 0.6129 | 0.6008 | 0.0848 | 0.024* | |
C33 | 0.81640 (12) | 0.72299 (9) | 0.17046 (8) | 0.0203 (2) | |
H33 | 0.8855 | 0.7557 | 0.1401 | 0.024* | |
C34 | 0.71305 (15) | 0.81187 (13) | 0.20703 (13) | 0.0395 (4) | |
H34A | 0.6715 | 0.8636 | 0.1560 | 0.059* | |
H34B | 0.7564 | 0.8454 | 0.2471 | 0.059* | |
H34C | 0.6462 | 0.7825 | 0.2410 | 0.059* | |
C35 | 0.88633 (18) | 0.63760 (12) | 0.24833 (10) | 0.0361 (3) | |
H35A | 0.9502 | 0.5834 | 0.2224 | 0.054* | |
H35B | 0.8212 | 0.6065 | 0.2827 | 0.054* | |
H35C | 0.9316 | 0.6693 | 0.2888 | 0.054* | |
O4A | 0.53591 (9) | 0.19130 (7) | 0.98022 (6) | 0.02402 (17) | |
O4B | 0.67023 (10) | 0.02596 (7) | 1.00905 (7) | 0.02782 (19) | |
H4B | 0.633 (2) | 0.0168 (17) | 0.9597 (15) | 0.045 (6)* | |
C41 | 0.62229 (11) | 0.12492 (9) | 1.02561 (7) | 0.01772 (18) | |
C42 | 0.68971 (10) | 0.14625 (8) | 1.11005 (7) | 0.01526 (17) | |
H42 | 0.6682 | 0.0998 | 1.1645 | 0.018* | |
N4 | 0.62721 (9) | 0.25923 (7) | 1.12166 (6) | 0.01644 (16) | |
H4A | 0.6638 | 0.2752 | 1.1705 | 0.025* | |
H4C | 0.5397 | 0.2673 | 1.1303 | 0.025* | |
H4D | 0.6410 | 0.3024 | 1.0711 | 0.025* | |
C43 | 0.84372 (11) | 0.12400 (9) | 1.10210 (8) | 0.01909 (19) | |
H43 | 0.8784 | 0.0465 | 1.1103 | 0.023* | |
C44 | 0.88945 (14) | 0.16861 (12) | 1.00713 (10) | 0.0302 (3) | |
H44A | 0.8505 | 0.1418 | 0.9597 | 0.045* | |
H44B | 0.9852 | 0.1471 | 1.0039 | 0.045* | |
H44C | 0.8614 | 0.2450 | 0.9982 | 0.045* | |
C45 | 0.90418 (12) | 0.16514 (11) | 1.18006 (9) | 0.0258 (2) | |
H45A | 0.8741 | 0.1361 | 1.2388 | 0.039* | |
H45B | 0.8762 | 0.2415 | 1.1721 | 0.039* | |
H45C | 1.0000 | 0.1435 | 1.1779 | 0.039* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.01572 (10) | 0.01488 (10) | 0.01617 (10) | −0.00331 (8) | −0.00024 (8) | −0.00355 (8) |
O11 | 0.0240 (4) | 0.0285 (4) | 0.0196 (4) | −0.0016 (3) | −0.0055 (3) | 0.0012 (3) |
O12 | 0.0244 (4) | 0.0269 (4) | 0.0217 (4) | −0.0112 (3) | 0.0025 (3) | 0.0040 (3) |
O13 | 0.0276 (4) | 0.0255 (4) | 0.0225 (4) | −0.0162 (3) | 0.0049 (3) | −0.0074 (3) |
O14 | 0.0273 (5) | 0.0269 (4) | 0.0362 (5) | 0.0070 (4) | −0.0081 (4) | −0.0191 (4) |
Cl2 | 0.01441 (10) | 0.01559 (10) | 0.01817 (11) | −0.00497 (8) | 0.00199 (8) | −0.00248 (8) |
O21 | 0.0307 (5) | 0.0366 (5) | 0.0229 (4) | −0.0107 (4) | 0.0129 (3) | −0.0079 (4) |
O22 | 0.0265 (5) | 0.0456 (6) | 0.0405 (6) | −0.0219 (4) | −0.0010 (4) | −0.0118 (5) |
O23 | 0.0258 (5) | 0.0247 (4) | 0.0419 (6) | −0.0007 (4) | 0.0009 (4) | 0.0142 (4) |
O24 | 0.0279 (4) | 0.0198 (4) | 0.0244 (4) | −0.0029 (3) | −0.0008 (3) | −0.0081 (3) |
Cl3 | 0.01736 (11) | 0.01462 (10) | 0.01771 (11) | −0.00293 (8) | −0.00001 (8) | −0.00137 (8) |
O31 | 0.0529 (7) | 0.0309 (6) | 0.0645 (8) | 0.0004 (5) | 0.0249 (6) | 0.0236 (6) |
O32 | 0.0223 (4) | 0.0368 (5) | 0.0351 (5) | 0.0003 (4) | 0.0066 (4) | −0.0115 (4) |
O33 | 0.0243 (4) | 0.0203 (4) | 0.0302 (4) | −0.0002 (3) | −0.0058 (3) | −0.0115 (3) |
O34 | 0.0375 (6) | 0.0400 (6) | 0.0454 (6) | 0.0068 (5) | −0.0205 (5) | −0.0244 (5) |
Cl4 | 0.01465 (10) | 0.01603 (10) | 0.01437 (10) | −0.00412 (8) | 0.00006 (7) | −0.00359 (8) |
O41 | 0.0227 (4) | 0.0295 (4) | 0.0205 (4) | −0.0031 (3) | −0.0075 (3) | −0.0010 (3) |
O42 | 0.0240 (4) | 0.0247 (4) | 0.0214 (4) | −0.0079 (3) | 0.0059 (3) | 0.0023 (3) |
O43 | 0.0246 (4) | 0.0223 (4) | 0.0216 (4) | −0.0129 (3) | 0.0011 (3) | −0.0045 (3) |
O44 | 0.0218 (4) | 0.0273 (4) | 0.0296 (4) | 0.0028 (3) | −0.0036 (3) | −0.0168 (4) |
O1A | 0.0281 (4) | 0.0242 (4) | 0.0242 (4) | −0.0068 (3) | 0.0110 (3) | −0.0075 (3) |
O1B | 0.0385 (5) | 0.0198 (4) | 0.0281 (4) | −0.0125 (4) | 0.0077 (4) | −0.0095 (3) |
C11 | 0.0214 (5) | 0.0149 (4) | 0.0168 (4) | −0.0034 (4) | 0.0015 (4) | −0.0026 (3) |
C12 | 0.0160 (4) | 0.0144 (4) | 0.0140 (4) | −0.0043 (3) | 0.0016 (3) | −0.0021 (3) |
N1 | 0.0151 (4) | 0.0167 (4) | 0.0184 (4) | −0.0047 (3) | −0.0002 (3) | −0.0037 (3) |
C13 | 0.0147 (4) | 0.0213 (5) | 0.0208 (5) | −0.0057 (4) | 0.0011 (3) | −0.0044 (4) |
C14 | 0.0214 (5) | 0.0289 (6) | 0.0267 (6) | −0.0058 (4) | −0.0079 (4) | 0.0003 (5) |
C15 | 0.0169 (5) | 0.0326 (6) | 0.0342 (6) | −0.0020 (4) | 0.0050 (4) | −0.0149 (5) |
O2A | 0.0265 (4) | 0.0216 (4) | 0.0223 (4) | 0.0001 (3) | −0.0088 (3) | −0.0048 (3) |
O2B | 0.0306 (5) | 0.0187 (4) | 0.0231 (4) | −0.0012 (3) | −0.0062 (3) | −0.0090 (3) |
C21 | 0.0161 (4) | 0.0173 (4) | 0.0165 (4) | −0.0037 (3) | 0.0001 (3) | −0.0049 (3) |
C22 | 0.0160 (4) | 0.0143 (4) | 0.0143 (4) | −0.0033 (3) | −0.0001 (3) | −0.0029 (3) |
N2 | 0.0169 (4) | 0.0159 (4) | 0.0164 (4) | −0.0029 (3) | −0.0004 (3) | −0.0048 (3) |
C23 | 0.0146 (4) | 0.0175 (4) | 0.0189 (4) | −0.0019 (3) | −0.0015 (3) | −0.0024 (4) |
C24 | 0.0209 (5) | 0.0303 (6) | 0.0253 (5) | −0.0045 (4) | −0.0060 (4) | −0.0069 (5) |
C25 | 0.0184 (5) | 0.0363 (7) | 0.0254 (6) | −0.0059 (5) | 0.0051 (4) | −0.0028 (5) |
O3A | 0.0195 (4) | 0.0162 (3) | 0.0193 (4) | −0.0013 (3) | 0.0048 (3) | −0.0016 (3) |
O3B | 0.0185 (4) | 0.0178 (4) | 0.0258 (4) | −0.0023 (3) | 0.0085 (3) | −0.0014 (3) |
C31 | 0.0143 (4) | 0.0178 (4) | 0.0140 (4) | −0.0019 (3) | 0.0009 (3) | −0.0022 (3) |
C32 | 0.0145 (4) | 0.0154 (4) | 0.0157 (4) | −0.0020 (3) | 0.0025 (3) | −0.0026 (3) |
N3 | 0.0153 (4) | 0.0166 (4) | 0.0165 (4) | −0.0032 (3) | 0.0024 (3) | −0.0036 (3) |
C33 | 0.0198 (5) | 0.0212 (5) | 0.0224 (5) | −0.0070 (4) | 0.0031 (4) | −0.0078 (4) |
C34 | 0.0291 (7) | 0.0372 (7) | 0.0588 (10) | −0.0060 (6) | 0.0056 (6) | −0.0325 (7) |
C35 | 0.0504 (9) | 0.0354 (7) | 0.0241 (6) | −0.0115 (6) | −0.0136 (6) | −0.0055 (5) |
O4A | 0.0236 (4) | 0.0264 (4) | 0.0212 (4) | −0.0023 (3) | −0.0058 (3) | −0.0057 (3) |
O4B | 0.0318 (5) | 0.0237 (4) | 0.0295 (5) | −0.0026 (4) | −0.0044 (4) | −0.0148 (4) |
C41 | 0.0179 (4) | 0.0199 (5) | 0.0170 (4) | −0.0054 (4) | 0.0015 (3) | −0.0068 (4) |
C42 | 0.0163 (4) | 0.0152 (4) | 0.0145 (4) | −0.0034 (3) | 0.0004 (3) | −0.0032 (3) |
N4 | 0.0173 (4) | 0.0165 (4) | 0.0160 (4) | −0.0034 (3) | −0.0003 (3) | −0.0049 (3) |
C43 | 0.0153 (4) | 0.0197 (5) | 0.0219 (5) | −0.0036 (4) | 0.0012 (4) | −0.0032 (4) |
C44 | 0.0257 (6) | 0.0394 (7) | 0.0266 (6) | −0.0111 (5) | 0.0096 (5) | −0.0039 (5) |
C45 | 0.0185 (5) | 0.0312 (6) | 0.0295 (6) | −0.0077 (4) | −0.0041 (4) | −0.0064 (5) |
Cl1—O11 | 1.4287 (9) | C23—C24 | 1.5339 (16) |
Cl1—O12 | 1.4497 (9) | C23—H23 | 0.98 |
Cl1—O13 | 1.4498 (9) | C24—H24A | 0.96 |
Cl1—O14 | 1.4560 (9) | C24—H24B | 0.96 |
Cl2—O21 | 1.4292 (9) | C24—H24C | 0.96 |
Cl2—O22 | 1.4327 (10) | C25—H25A | 0.96 |
Cl2—O23 | 1.4456 (10) | C25—H25B | 0.96 |
Cl2—O24 | 1.4543 (9) | C25—H25C | 0.96 |
Cl3—O31 | 1.4269 (11) | O3A—C31 | 1.2248 (13) |
Cl3—O32 | 1.4337 (10) | O3B—C31 | 1.3064 (13) |
Cl3—O33 | 1.4416 (9) | O3B—H3B | 0.90 (2) |
Cl3—O34 | 1.4547 (10) | C31—C32 | 1.5208 (14) |
Cl4—O41 | 1.4342 (9) | C32—N3 | 1.4989 (14) |
Cl4—O42 | 1.4471 (9) | C32—C33 | 1.5484 (16) |
Cl4—O43 | 1.4475 (8) | C32—H32 | 0.98 |
Cl4—O44 | 1.4596 (9) | N3—H3A | 0.89 |
O1A—C11 | 1.2132 (14) | N3—H3C | 0.89 |
O1B—C11 | 1.3161 (14) | N3—H3D | 0.89 |
O1B—H1B | 0.86 (2) | C33—C34 | 1.5261 (17) |
C11—C12 | 1.5190 (15) | C33—C35 | 1.5269 (19) |
C12—N1 | 1.4953 (13) | C33—H33 | 0.98 |
C12—C13 | 1.5443 (15) | C34—H34A | 0.96 |
C12—H12 | 0.98 | C34—H34B | 0.96 |
N1—H1A | 0.89 | C34—H34C | 0.96 |
N1—H1C | 0.89 | C35—H35A | 0.96 |
N1—H1D | 0.89 | C35—H35B | 0.96 |
C13—C14 | 1.5309 (17) | C35—H35C | 0.96 |
C13—C15 | 1.5345 (17) | O4A—C41 | 1.2121 (14) |
C13—H13 | 0.98 | O4B—C41 | 1.3262 (14) |
C14—H14A | 0.96 | O4B—H4B | 0.86 (2) |
C14—H14B | 0.96 | C41—C42 | 1.5254 (15) |
C14—H14C | 0.96 | C42—N4 | 1.4962 (13) |
C15—H15A | 0.96 | C42—C43 | 1.5463 (15) |
C15—H15B | 0.96 | C42—H42 | 0.98 |
C15—H15C | 0.96 | N4—H4A | 0.89 |
O2A—C21 | 1.2141 (13) | N4—H4C | 0.89 |
O2B—C21 | 1.3209 (13) | N4—H4D | 0.89 |
O2B—H2B | 0.87 (2) | C43—C44 | 1.5301 (17) |
C21—C22 | 1.5212 (15) | C43—C45 | 1.5369 (17) |
C22—N2 | 1.4966 (13) | C43—H43 | 0.98 |
C22—C23 | 1.5453 (15) | C44—H44A | 0.96 |
C22—H22 | 0.98 | C44—H44B | 0.96 |
N2—H2A | 0.89 | C44—H44C | 0.96 |
N2—H2C | 0.89 | C45—H45A | 0.96 |
N2—H2D | 0.89 | C45—H45B | 0.96 |
C23—C25 | 1.5320 (16) | C45—H45C | 0.96 |
O11—Cl1—O12 | 110.58 (6) | C23—C24—H24A | 109.5 |
O11—Cl1—O13 | 110.72 (6) | C23—C24—H24B | 109.5 |
O12—Cl1—O13 | 107.98 (5) | H24A—C24—H24B | 109.5 |
O11—Cl1—O14 | 109.70 (6) | C23—C24—H24C | 109.5 |
O12—Cl1—O14 | 109.19 (6) | H24A—C24—H24C | 109.5 |
O13—Cl1—O14 | 108.63 (6) | H24B—C24—H24C | 109.5 |
O21—Cl2—O22 | 111.14 (6) | C23—C25—H25A | 109.5 |
O21—Cl2—O23 | 109.52 (6) | C23—C25—H25B | 109.5 |
O22—Cl2—O23 | 110.61 (7) | H25A—C25—H25B | 109.5 |
O21—Cl2—O24 | 109.24 (6) | C23—C25—H25C | 109.5 |
O22—Cl2—O24 | 108.44 (6) | H25A—C25—H25C | 109.5 |
O23—Cl2—O24 | 107.81 (6) | H25B—C25—H25C | 109.5 |
O31—Cl3—O32 | 109.92 (7) | C31—O3B—H3B | 109.2 (13) |
O31—Cl3—O33 | 110.00 (7) | O3A—C31—O3B | 125.86 (10) |
O32—Cl3—O33 | 111.06 (6) | O3A—C31—C32 | 121.89 (9) |
O31—Cl3—O34 | 108.49 (9) | O3B—C31—C32 | 112.21 (9) |
O32—Cl3—O34 | 109.04 (7) | N3—C32—C31 | 107.69 (8) |
O33—Cl3—O34 | 108.27 (6) | N3—C32—C33 | 113.06 (9) |
O41—Cl4—O42 | 110.42 (6) | C31—C32—C33 | 110.13 (9) |
O41—Cl4—O43 | 110.43 (5) | N3—C32—H32 | 108.6 |
O42—Cl4—O43 | 108.45 (5) | C31—C32—H32 | 108.6 |
O41—Cl4—O44 | 109.33 (5) | C33—C32—H32 | 108.6 |
O42—Cl4—O44 | 109.40 (6) | C32—N3—H3A | 109.5 |
O43—Cl4—O44 | 108.78 (5) | C32—N3—H3C | 109.5 |
C11—O1B—H1B | 108.8 (13) | H3A—N3—H3C | 109.5 |
O1A—C11—O1B | 125.16 (10) | C32—N3—H3D | 109.5 |
O1A—C11—C12 | 122.82 (10) | H3A—N3—H3D | 109.5 |
O1B—C11—C12 | 112.02 (9) | H3C—N3—H3D | 109.5 |
N1—C12—C11 | 107.12 (8) | C34—C33—C35 | 112.19 (12) |
N1—C12—C13 | 112.34 (8) | C34—C33—C32 | 111.18 (10) |
C11—C12—C13 | 113.40 (9) | C35—C33—C32 | 113.27 (10) |
N1—C12—H12 | 107.9 | C34—C33—H33 | 106.6 |
C11—C12—H12 | 107.9 | C35—C33—H33 | 106.6 |
C13—C12—H12 | 107.9 | C32—C33—H33 | 106.6 |
C12—N1—H1A | 109.5 | C33—C34—H34A | 109.5 |
C12—N1—H1C | 109.5 | C33—C34—H34B | 109.5 |
H1A—N1—H1C | 109.5 | H34A—C34—H34B | 109.5 |
C12—N1—H1D | 109.5 | C33—C34—H34C | 109.5 |
H1A—N1—H1D | 109.5 | H34A—C34—H34C | 109.5 |
H1C—N1—H1D | 109.5 | H34B—C34—H34C | 109.5 |
C14—C13—C15 | 112.01 (10) | C33—C35—H35A | 109.5 |
C14—C13—C12 | 112.93 (9) | C33—C35—H35B | 109.5 |
C15—C13—C12 | 110.41 (9) | H35A—C35—H35B | 109.5 |
C14—C13—H13 | 107.0 | C33—C35—H35C | 109.5 |
C15—C13—H13 | 107.0 | H35A—C35—H35C | 109.5 |
C12—C13—H13 | 107.0 | H35B—C35—H35C | 109.5 |
C13—C14—H14A | 109.5 | C41—O4B—H4B | 109.7 (14) |
C13—C14—H14B | 109.5 | O4A—C41—O4B | 125.17 (10) |
H14A—C14—H14B | 109.5 | O4A—C41—C42 | 123.30 (10) |
C13—C14—H14C | 109.5 | O4B—C41—C42 | 111.53 (9) |
H14A—C14—H14C | 109.5 | N4—C42—C41 | 106.44 (8) |
H14B—C14—H14C | 109.5 | N4—C42—C43 | 112.39 (9) |
C13—C15—H15A | 109.5 | C41—C42—C43 | 113.14 (9) |
C13—C15—H15B | 109.5 | N4—C42—H42 | 108.2 |
H15A—C15—H15B | 109.5 | C41—C42—H42 | 108.2 |
C13—C15—H15C | 109.5 | C43—C42—H42 | 108.2 |
H15A—C15—H15C | 109.5 | C42—N4—H4A | 109.5 |
H15B—C15—H15C | 109.5 | C42—N4—H4C | 109.5 |
C21—O2B—H2B | 110.7 (13) | H4A—N4—H4C | 109.5 |
O2A—C21—O2B | 124.84 (10) | C42—N4—H4D | 109.5 |
O2A—C21—C22 | 123.15 (10) | H4A—N4—H4D | 109.5 |
O2B—C21—C22 | 112.02 (9) | H4C—N4—H4D | 109.5 |
N2—C22—C21 | 106.83 (8) | C44—C43—C45 | 111.04 (10) |
N2—C22—C23 | 113.00 (8) | C44—C43—C42 | 112.87 (10) |
C21—C22—C23 | 113.28 (9) | C45—C43—C42 | 110.94 (9) |
N2—C22—H22 | 107.8 | C44—C43—H43 | 107.2 |
C21—C22—H22 | 107.8 | C45—C43—H43 | 107.2 |
C23—C22—H22 | 107.8 | C42—C43—H43 | 107.2 |
C22—N2—H2A | 109.5 | C43—C44—H44A | 109.5 |
C22—N2—H2C | 109.5 | C43—C44—H44B | 109.5 |
H2A—N2—H2C | 109.5 | H44A—C44—H44B | 109.5 |
C22—N2—H2D | 109.5 | C43—C44—H44C | 109.5 |
H2A—N2—H2D | 109.5 | H44A—C44—H44C | 109.5 |
H2C—N2—H2D | 109.5 | H44B—C44—H44C | 109.5 |
C25—C23—C24 | 111.38 (10) | C43—C45—H45A | 109.5 |
C25—C23—C22 | 112.90 (9) | C43—C45—H45B | 109.5 |
C24—C23—C22 | 110.96 (9) | H45A—C45—H45B | 109.5 |
C25—C23—H23 | 107.1 | C43—C45—H45C | 109.5 |
C24—C23—H23 | 107.1 | H45A—C45—H45C | 109.5 |
C22—C23—H23 | 107.1 | H45B—C45—H45C | 109.5 |
O1A—C11—C12—N1 | 2.09 (14) | O3A—C31—C32—N3 | −20.98 (14) |
O1B—C11—C12—N1 | −177.91 (9) | O3B—C31—C32—N3 | 161.07 (9) |
O1A—C11—C12—C13 | −122.43 (12) | O3A—C31—C32—C33 | 102.72 (12) |
O1B—C11—C12—C13 | 57.57 (12) | O3B—C31—C32—C33 | −75.23 (11) |
N1—C12—C13—C14 | −73.50 (12) | N3—C32—C33—C34 | −64.56 (13) |
C11—C12—C13—C14 | 48.14 (13) | C31—C32—C33—C34 | 174.92 (11) |
N1—C12—C13—C15 | 52.77 (12) | N3—C32—C33—C35 | 62.85 (13) |
C11—C12—C13—C15 | 174.41 (10) | C31—C32—C33—C35 | −57.67 (13) |
O2A—C21—C22—N2 | 1.11 (14) | O4A—C41—C42—N4 | 0.30 (15) |
O2B—C21—C22—N2 | −179.21 (9) | O4B—C41—C42—N4 | −179.76 (9) |
O2A—C21—C22—C23 | 126.19 (12) | O4A—C41—C42—C43 | −123.63 (12) |
O2B—C21—C22—C23 | −54.14 (12) | O4B—C41—C42—C43 | 56.32 (13) |
N2—C22—C23—C24 | −53.19 (12) | N4—C42—C43—C44 | −75.99 (12) |
C21—C22—C23—C24 | −174.87 (9) | C41—C42—C43—C44 | 44.61 (13) |
N2—C22—C23—C25 | 72.66 (12) | N4—C42—C43—C45 | 49.37 (12) |
C21—C22—C23—C25 | −49.02 (13) | C41—C42—C43—C45 | 169.97 (10) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1B—H1B···O34i | 0.86 (2) | 1.89 (2) | 2.7503 (14) | 177 (2) |
N1—H1A···O24ii | 0.89 | 2.15 | 2.8349 (13) | 133 |
N1—H1C···O2A | 0.89 | 2.15 | 2.8670 (12) | 137 |
N1—H1D···O12ii | 0.89 | 2.27 | 2.9264 (13) | 130 |
O2B—H2B···O44i | 0.87 (2) | 1.88 (2) | 2.7395 (12) | 175 (2) |
N2—H2A···O13i | 0.89 | 2.19 | 2.9124 (13) | 138 |
N2—H2A···O12i | 0.89 | 2.51 | 3.3055 (13) | 149 |
N2—H2C···O23i | 0.89 | 2.02 | 2.8695 (13) | 159 |
N2—H2D···O24ii | 0.89 | 2.15 | 2.9234 (13) | 145 |
N2—H2D···O43 | 0.89 | 2.31 | 2.9731 (13) | 132 |
O3B—H3B···O3Aiii | 0.90 (2) | 1.74 (2) | 2.6381 (11) | 174 (2) |
N3—H3A···O1Ai | 0.89 | 2.09 | 2.9288 (12) | 158 |
N3—H3D···O33iv | 0.89 | 2.25 | 2.9745 (13) | 139 |
N3—H3C···O42 | 0.89 | 2.10 | 2.9546 (13) | 161 |
O4B—H4B···O14ii | 0.86 (2) | 1.93 (2) | 2.7913 (13) | 172 (2) |
N4—H4A···O43v | 0.89 | 2.20 | 2.9049 (12) | 135 |
N4—H4A···O42v | 0.89 | 2.51 | 3.3032 (13) | 148 |
N4—H4C···O13vi | 0.89 | 2.16 | 2.8827 (13) | 138 |
N4—H4C···O33v | 0.89 | 2.32 | 2.9834 (13) | 132 |
N4—H4D···O31i | 0.89 | 1.95 | 2.8208 (14) | 165 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x, y−1, z; (iii) −x+2, −y+1, −z; (iv) −x+1, −y+1, −z; (v) x, y, z+1; (vi) −x+1, −y+1, −z+2. |