Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807014912/si2008sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807014912/si2008Isup2.hkl |
CCDC reference: 647328
Key indicators
- Single-crystal X-ray study
- T = 100 K
- Mean (C-C) = 0.002 Å
- Disorder in main residue
- R factor = 0.028
- wR factor = 0.073
- Data-to-parameter ratio = 24.3
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings Differ .... ? PLAT077_ALERT_4_C Unitcell contains non-integer number of atoms .. ? PLAT301_ALERT_3_C Main Residue Disorder ......................... 22.00 Perc. PLAT410_ALERT_2_C Short Intra H...H Contact H2A .. H52A .. 1.97 Ang. PLAT410_ALERT_2_C Short Intra H...H Contact H2B .. H52B .. 1.91 Ang. PLAT431_ALERT_2_C Short Inter HL..A Contact Cl2B .. O12A .. 3.15 Ang.
Alert level G 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 30.03 From the CIF: _reflns_number_total 7948 Count of symmetry unique reflns 4427 Completeness (_total/calc) 179.53% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 3521 Fraction of Friedel pairs measured 0.795 Are heavy atom types Z>Si present yes PLAT791_ALERT_1_G Confirm the Absolute Configuration of C2A = . S PLAT791_ALERT_1_G Confirm the Absolute Configuration of C2B = . S
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 6 ALERT level C = Check and explain 3 ALERT level G = General alerts; check 3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 3 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
checkCIF publication errors
Alert level A PUBL024_ALERT_1_A The number of authors is greater than 5. Please specify the role of each of the co-authors for your paper.
Author Response: All authors were implied in this work : the synthese was carried out by G. Lena under the supervision of G. Guichard, and M. Gellenoncourt & E. Durain (master sudents) solved the structure under the supervision of E. Aubert & C. Didierjean |
1 ALERT level A = Data missing that is essential or data in wrong format 0 ALERT level G = General alerts. Data that may be required is missing
Data collection: COLLECT (Nonius, 1998); cell refinement: COLLECT; data reduction: HKL Suite (Otwinowski & Minor, 1997); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2003).
C8H15N3O2·0.94CDCl3 | F(000) = 1235.5 |
Mr = 298.20 | Dx = 1.455 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 115224 reflections |
a = 11.8160 (2) Å | θ = 3.4–35.9° |
b = 12.5893 (3) Å | µ = 0.63 mm−1 |
c = 18.3033 (4) Å | T = 100 K |
V = 2722.71 (10) Å3 | Prism, colorless |
Z = 8 | 0.30 × 0.20 × 0.12 mm |
Bruker–Nonius KappaCCD diffractometer | 7948 independent reflections |
Radiation source: fine-focus sealed tube | 7592 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.043 |
oscillation scans | θmax = 30.0°, θmin = 3.4° |
Absorption correction: multi-scan (SORTAV; Blessing, 1995) | h = −16→16 |
Tmin = 0.86, Tmax = 0.93 | k = −17→17 |
115224 measured reflections | l = −25→25 |
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)] = 0.028 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.073 | w = 1/[σ2(Fo2) + (0.0396P)2 + 0.8038P] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max = 0.003 |
7948 reflections | Δρmax = 0.65 e Å−3 |
327 parameters | Δρmin = −0.39 e Å−3 |
4 restraints | Absolute structure: Flack (1983), 3529 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: −0.02 (3) |
Experimental. There is no ambiguity in locating atoms H2A, H2B, H52A and H52B. The short H2A···H52A (1.97 A) and H2B···H52B (1.91 A) contacts are inevitable and are a characteristic of the molecule. |
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 | Occ. (<1) | |
N1A | 0.18280 (9) | 0.46197 (9) | 0.41776 (6) | 0.0157 (2) | |
H1A | 0.1349 (13) | 0.5130 (11) | 0.4212 (10) | 0.019* | |
C2A | 0.30213 (10) | 0.49362 (10) | 0.40985 (7) | 0.0149 (2) | |
H2A | 0.3414 | 0.4418 | 0.3771 | 0.018* | |
C3A | 0.35538 (10) | 0.48808 (10) | 0.48609 (7) | 0.0154 (2) | |
N4A | 0.37041 (10) | 0.38847 (8) | 0.51205 (6) | 0.0164 (2) | |
C5A | 0.33685 (11) | 0.29656 (10) | 0.46875 (7) | 0.0161 (2) | |
H51A | 0.3657 | 0.2314 | 0.4926 | 0.019* | |
H52A | 0.3726 | 0.3016 | 0.4199 | 0.019* | |
N6A | 0.21434 (10) | 0.28717 (8) | 0.45962 (6) | 0.0161 (2) | |
H6A | 0.1844 (15) | 0.2291 (10) | 0.4740 (10) | 0.019* | |
C7A | 0.14228 (11) | 0.36686 (10) | 0.44210 (7) | 0.0146 (2) | |
O8A | 0.03741 (8) | 0.35363 (8) | 0.44631 (6) | 0.01946 (19) | |
C9A | 0.24199 (13) | 0.60880 (13) | 0.30426 (9) | 0.0274 (3) | |
H9C | 0.2704 | 0.5542 | 0.2708 | 0.041* | |
H9B | 0.2512 | 0.6790 | 0.2818 | 0.041* | |
H9A | 0.1617 | 0.5960 | 0.3143 | 0.041* | |
C10A | 0.30861 (11) | 0.60453 (10) | 0.37571 (8) | 0.0184 (2) | |
H10A | 0.2747 | 0.6567 | 0.4106 | 0.022* | |
C11A | 0.43219 (13) | 0.63583 (13) | 0.36188 (9) | 0.0285 (3) | |
H11B | 0.4647 | 0.5889 | 0.3247 | 0.043* | |
H11A | 0.4754 | 0.6291 | 0.4074 | 0.043* | |
H11C | 0.4354 | 0.7095 | 0.3447 | 0.043* | |
O12A | 0.37477 (10) | 0.56798 (8) | 0.52296 (6) | 0.0217 (2) | |
C13A | 0.40486 (12) | 0.37385 (11) | 0.58849 (7) | 0.0204 (3) | |
H13C | 0.4616 | 0.4274 | 0.6014 | 0.031* | |
H13B | 0.4372 | 0.3027 | 0.5947 | 0.031* | |
H13A | 0.3387 | 0.3817 | 0.6204 | 0.031* | |
C14A | 0.02087 (13) | 0.48301 (12) | 0.60569 (8) | 0.0218 (3) | 0.9332 (18) |
D14A | 0.0421 | 0.4974 | 0.5537 | 0.026* | 0.9332 (18) |
Cl1A | −0.12767 (3) | 0.48035 (4) | 0.61249 (2) | 0.03235 (11) | 0.9332 (18) |
Cl2A | 0.07801 (4) | 0.58346 (3) | 0.66102 (3) | 0.03573 (12) | 0.9332 (18) |
Cl3A | 0.07565 (4) | 0.35807 (3) | 0.63123 (2) | 0.03509 (12) | 0.9332 (18) |
N1B | 0.88013 (9) | 0.52725 (8) | 0.41896 (6) | 0.0154 (2) | |
H1B | 0.9249 (13) | 0.4738 (11) | 0.4239 (10) | 0.018* | |
C2B | 0.76333 (10) | 0.50803 (10) | 0.39525 (7) | 0.0157 (2) | |
H2B | 0.7395 | 0.5670 | 0.3620 | 0.019* | |
C3B | 0.69020 (10) | 0.51173 (10) | 0.46466 (7) | 0.0166 (2) | |
N4B | 0.67715 (9) | 0.61094 (9) | 0.49265 (6) | 0.0163 (2) | |
C5B | 0.72761 (11) | 0.70217 (10) | 0.45606 (7) | 0.0161 (2) | |
H51B | 0.6984 | 0.7681 | 0.4787 | 0.019* | |
H52B | 0.7043 | 0.7021 | 0.4041 | 0.019* | |
N6B | 0.85092 (10) | 0.70216 (8) | 0.46013 (7) | 0.0174 (2) | |
H6B | 0.8784 (16) | 0.7625 (10) | 0.4727 (10) | 0.021* | |
C7B | 0.92158 (11) | 0.61942 (9) | 0.44700 (7) | 0.0148 (2) | |
O8B | 1.02506 (8) | 0.62679 (8) | 0.46138 (5) | 0.01870 (19) | |
C9B | 0.84041 (15) | 0.39590 (13) | 0.29207 (9) | 0.0289 (3) | |
H9F | 0.8265 | 0.4531 | 0.2569 | 0.043* | |
H9E | 0.8334 | 0.3271 | 0.2674 | 0.043* | |
H9D | 0.9168 | 0.4032 | 0.3122 | 0.043* | |
C10B | 0.75372 (12) | 0.40261 (11) | 0.35391 (8) | 0.0206 (3) | |
H10B | 0.7671 | 0.3428 | 0.3888 | 0.025* | |
C11B | 0.63368 (14) | 0.39284 (12) | 0.32243 (9) | 0.0284 (3) | |
H11D | 0.5786 | 0.3930 | 0.3624 | 0.043* | |
H11F | 0.6272 | 0.3263 | 0.2950 | 0.043* | |
H11E | 0.6187 | 0.4530 | 0.2898 | 0.043* | |
O12B | 0.65458 (9) | 0.43146 (8) | 0.49511 (6) | 0.0229 (2) | |
C13B | 0.63484 (12) | 0.62620 (11) | 0.56728 (8) | 0.0210 (3) | |
H13F | 0.5945 | 0.5622 | 0.5831 | 0.032* | |
H13E | 0.5831 | 0.6870 | 0.5683 | 0.032* | |
H13D | 0.6986 | 0.6396 | 0.6002 | 0.032* | |
C14B | 0.86173 (14) | 0.78060 (13) | 0.23789 (8) | 0.0247 (3) | 0.9438 (19) |
D14B | 0.8864 | 0.8154 | 0.1914 | 0.030* | 0.9438 (19) |
Cl1B | 0.71770 (4) | 0.74372 (4) | 0.22941 (2) | 0.03357 (11) | 0.9438 (19) |
Cl2B | 0.87924 (4) | 0.87097 (3) | 0.31001 (2) | 0.03148 (10) | 0.9438 (19) |
Cl3B | 0.94561 (4) | 0.66736 (4) | 0.25248 (3) | 0.03840 (12) | 0.9438 (19) |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1A | 0.0134 (5) | 0.0126 (5) | 0.0213 (5) | −0.0002 (4) | 0.0023 (4) | |
C2A | 0.0136 (5) | 0.0120 (5) | 0.0190 (5) | 0.0012 (4) | 0.0006 (4) | |
C3A | 0.0136 (5) | 0.0121 (5) | 0.0206 (6) | 0.0000 (4) | 0.0003 (4) | |
N4A | 0.0172 (5) | 0.0115 (4) | 0.0204 (5) | −0.0036 (4) | 0.0006 (4) | |
C5A | 0.0156 (5) | 0.0109 (5) | 0.0219 (6) | −0.0011 (4) | −0.0018 (4) | |
N6A | 0.0152 (5) | 0.0100 (4) | 0.0229 (5) | −0.0011 (4) | 0.0000 (4) | |
C7A | 0.0158 (5) | 0.0122 (5) | 0.0157 (5) | −0.0004 (4) | −0.0014 (4) | |
O8A | 0.0140 (4) | 0.0153 (4) | 0.0291 (5) | −0.0018 (4) | 0.0024 (4) | |
C9A | 0.0277 (7) | 0.0270 (7) | 0.0274 (7) | −0.0012 (6) | 0.0133 (6) | |
C10A | 0.0176 (6) | 0.0131 (5) | 0.0244 (6) | 0.0017 (5) | 0.0049 (5) | |
C11A | 0.0205 (7) | 0.0256 (7) | 0.0394 (8) | 0.0005 (6) | 0.0128 (6) | |
O12A | 0.0265 (5) | 0.0124 (4) | 0.0263 (5) | −0.0047 (4) | −0.0027 (3) | |
C13A | 0.0227 (6) | 0.0159 (5) | 0.0225 (6) | −0.0063 (5) | 0.0012 (5) | |
C14A | 0.0203 (6) | 0.0242 (7) | 0.0209 (6) | 0.0000 (5) | 0.0031 (5) | |
Cl1A | 0.01957 (17) | 0.0443 (2) | 0.0332 (2) | −0.00137 (15) | 0.00822 (18) | |
Cl2A | 0.0382 (2) | 0.02379 (19) | 0.0452 (2) | −0.00856 (19) | 0.00173 (17) | |
Cl3A | 0.0444 (3) | 0.0263 (2) | 0.0345 (2) | −0.01454 (18) | −0.00395 (16) | |
N1B | 0.0131 (4) | 0.0113 (4) | 0.0217 (5) | −0.0010 (4) | −0.0020 (4) | |
C2B | 0.0147 (5) | 0.0114 (5) | 0.0209 (6) | −0.0029 (4) | −0.0012 (4) | |
C3B | 0.0122 (5) | 0.0141 (5) | 0.0236 (6) | −0.0018 (4) | −0.0001 (5) | |
N4B | 0.0141 (5) | 0.0129 (5) | 0.0217 (5) | 0.0008 (4) | 0.0000 (4) | |
C5B | 0.0164 (5) | 0.0099 (5) | 0.0220 (6) | −0.0017 (5) | 0.0016 (4) | |
N6B | 0.0153 (5) | 0.0089 (4) | 0.0280 (6) | −0.0006 (4) | −0.0013 (4) | |
C7B | 0.0163 (5) | 0.0116 (5) | 0.0165 (5) | 0.0011 (4) | 0.0011 (4) | |
O8B | 0.0143 (4) | 0.0153 (4) | 0.0266 (5) | −0.0009 (3) | −0.0023 (4) | |
C9B | 0.0330 (8) | 0.0253 (7) | 0.0284 (7) | 0.0027 (6) | −0.0126 (6) | |
C10B | 0.0213 (6) | 0.0133 (6) | 0.0272 (7) | −0.0040 (5) | −0.0038 (5) | |
C11B | 0.0273 (7) | 0.0208 (6) | 0.0371 (8) | −0.0097 (6) | −0.0063 (6) | |
O12B | 0.0208 (5) | 0.0138 (4) | 0.0341 (5) | 0.0043 (4) | 0.0032 (4) | |
C13B | 0.0194 (6) | 0.0193 (6) | 0.0244 (6) | 0.0051 (5) | −0.0023 (5) | |
C14B | 0.0294 (8) | 0.0281 (7) | 0.0166 (6) | −0.0019 (5) | 0.0045 (5) | |
Cl1B | 0.0314 (2) | 0.0409 (2) | 0.02838 (19) | −0.00681 (15) | −0.00436 (16) | |
Cl2B | 0.0315 (2) | 0.0306 (2) | 0.0324 (2) | −0.00753 (16) | −0.00732 (16) | |
Cl3B | 0.0404 (2) | 0.0323 (2) | 0.0425 (2) | 0.01073 (19) | 0.00303 (18) |
N1A—C7A | 1.3643 (16) | N1B—C7B | 1.3601 (16) |
N1A—C2A | 1.4723 (16) | N1B—C2B | 1.4669 (16) |
N1A—H1A | 0.859 (9) | N1B—H1B | 0.861 (9) |
C2A—C10A | 1.5317 (17) | C2B—C10B | 1.5318 (18) |
C2A—C3A | 1.5323 (18) | C2B—C3B | 1.5372 (18) |
C2A—H2A | 1.0000 | C2B—H2B | 1.0000 |
C3A—O12A | 1.2328 (16) | C3B—O12B | 1.2284 (16) |
C3A—N4A | 1.3527 (16) | C3B—N4B | 1.3587 (17) |
N4A—C5A | 1.4575 (16) | N4B—C5B | 1.4571 (16) |
N4A—C13A | 1.4686 (17) | N4B—C13B | 1.4672 (17) |
C5A—N6A | 1.4619 (16) | C5B—N6B | 1.4590 (17) |
C5A—H51A | 0.9900 | C5B—H51B | 0.9900 |
C5A—H52A | 0.9900 | C5B—H52B | 0.9900 |
N6A—C7A | 1.3543 (16) | N6B—C7B | 1.3564 (16) |
N6A—H6A | 0.854 (9) | N6B—H6B | 0.858 (9) |
C7A—O8A | 1.2527 (16) | C7B—O8B | 1.2542 (16) |
C9A—C10A | 1.527 (2) | C9B—C10B | 1.529 (2) |
C9A—H9C | 0.9800 | C9B—H9F | 0.9800 |
C9A—H9B | 0.9800 | C9B—H9E | 0.9800 |
C9A—H9A | 0.9800 | C9B—H9D | 0.9800 |
C10A—C11A | 1.5334 (19) | C10B—C11B | 1.536 (2) |
C10A—H10A | 1.0000 | C10B—H10B | 1.0000 |
C11A—H11B | 0.9800 | C11B—H11D | 0.9800 |
C11A—H11A | 0.9800 | C11B—H11F | 0.9800 |
C11A—H11C | 0.9800 | C11B—H11E | 0.9800 |
C13A—H13C | 0.9800 | C13B—H13F | 0.9800 |
C13A—H13B | 0.9800 | C13B—H13E | 0.9800 |
C13A—H13A | 0.9800 | C13B—H13D | 0.9800 |
C14A—Cl2A | 1.7552 (17) | C14B—Cl2B | 1.7550 (17) |
C14A—Cl1A | 1.7599 (16) | C14B—Cl3B | 1.7568 (17) |
C14A—Cl3A | 1.7639 (15) | C14B—Cl1B | 1.7708 (18) |
C14A—D14A | 1.0000 | C14B—D14B | 1.0000 |
C7A—N1A—C2A | 127.28 (11) | C7B—N1B—C2B | 126.24 (11) |
C7A—N1A—H1A | 113.7 (12) | C7B—N1B—H1B | 114.0 (12) |
C2A—N1A—H1A | 115.9 (12) | C2B—N1B—H1B | 118.7 (13) |
N1A—C2A—C10A | 109.55 (10) | N1B—C2B—C10B | 111.02 (10) |
N1A—C2A—C3A | 106.95 (10) | N1B—C2B—C3B | 106.22 (10) |
C10A—C2A—C3A | 113.11 (11) | C10B—C2B—C3B | 113.13 (11) |
N1A—C2A—H2A | 109.0 | N1B—C2B—H2B | 108.8 |
C10A—C2A—H2A | 109.0 | C10B—C2B—H2B | 108.8 |
C3A—C2A—H2A | 109.0 | C3B—C2B—H2B | 108.8 |
O12A—C3A—N4A | 122.67 (12) | O12B—C3B—N4B | 123.11 (12) |
O12A—C3A—C2A | 122.53 (11) | O12B—C3B—C2B | 122.86 (12) |
N4A—C3A—C2A | 114.58 (11) | N4B—C3B—C2B | 113.79 (11) |
C3A—N4A—C5A | 120.61 (11) | C3B—N4B—C5B | 120.32 (11) |
C3A—N4A—C13A | 119.15 (11) | C3B—N4B—C13B | 120.67 (11) |
C5A—N4A—C13A | 119.60 (10) | C5B—N4B—C13B | 117.65 (10) |
N4A—C5A—N6A | 113.31 (10) | N4B—C5B—N6B | 112.65 (10) |
N4A—C5A—H51A | 108.9 | N4B—C5B—H51B | 109.1 |
N6A—C5A—H51A | 108.9 | N6B—C5B—H51B | 109.1 |
N4A—C5A—H52A | 108.9 | N4B—C5B—H52B | 109.1 |
N6A—C5A—H52A | 108.9 | N6B—C5B—H52B | 109.1 |
H51A—C5A—H52A | 107.7 | H51B—C5B—H52B | 107.8 |
C7A—N6A—C5A | 126.14 (11) | C7B—N6B—C5B | 127.28 (11) |
C7A—N6A—H6A | 116.5 (13) | C7B—N6B—H6B | 119.6 (13) |
C5A—N6A—H6A | 116.4 (13) | C5B—N6B—H6B | 113.1 (13) |
O8A—C7A—N6A | 120.59 (12) | O8B—C7B—N6B | 120.41 (11) |
O8A—C7A—N1A | 118.94 (11) | O8B—C7B—N1B | 119.56 (11) |
N6A—C7A—N1A | 120.45 (12) | N6B—C7B—N1B | 120.03 (12) |
C10A—C9A—H9C | 109.5 | C10B—C9B—H9F | 109.5 |
C10A—C9A—H9B | 109.5 | C10B—C9B—H9E | 109.5 |
H9C—C9A—H9B | 109.5 | H9F—C9B—H9E | 109.5 |
C10A—C9A—H9A | 109.5 | C10B—C9B—H9D | 109.5 |
H9C—C9A—H9A | 109.5 | H9F—C9B—H9D | 109.5 |
H9B—C9A—H9A | 109.5 | H9E—C9B—H9D | 109.5 |
C9A—C10A—C2A | 110.84 (11) | C9B—C10B—C2B | 111.34 (11) |
C9A—C10A—C11A | 109.90 (12) | C9B—C10B—C11B | 109.67 (13) |
C2A—C10A—C11A | 110.44 (11) | C2B—C10B—C11B | 108.85 (11) |
C9A—C10A—H10A | 108.5 | C9B—C10B—H10B | 109.0 |
C2A—C10A—H10A | 108.5 | C2B—C10B—H10B | 109.0 |
C11A—C10A—H10A | 108.5 | C11B—C10B—H10B | 109.0 |
C10A—C11A—H11B | 109.5 | C10B—C11B—H11D | 109.5 |
C10A—C11A—H11A | 109.5 | C10B—C11B—H11F | 109.5 |
H11B—C11A—H11A | 109.5 | H11D—C11B—H11F | 109.5 |
C10A—C11A—H11C | 109.5 | C10B—C11B—H11E | 109.5 |
H11B—C11A—H11C | 109.5 | H11D—C11B—H11E | 109.5 |
H11A—C11A—H11C | 109.5 | H11F—C11B—H11E | 109.5 |
N4A—C13A—H13C | 109.5 | N4B—C13B—H13F | 109.5 |
N4A—C13A—H13B | 109.5 | N4B—C13B—H13E | 109.5 |
H13C—C13A—H13B | 109.5 | H13F—C13B—H13E | 109.5 |
N4A—C13A—H13A | 109.5 | N4B—C13B—H13D | 109.5 |
H13C—C13A—H13A | 109.5 | H13F—C13B—H13D | 109.5 |
H13B—C13A—H13A | 109.5 | H13E—C13B—H13D | 109.5 |
Cl2A—C14A—Cl1A | 110.88 (9) | Cl2B—C14B—Cl3B | 110.19 (9) |
Cl2A—C14A—Cl3A | 110.39 (8) | Cl2B—C14B—Cl1B | 110.44 (9) |
Cl1A—C14A—Cl3A | 109.28 (9) | Cl3B—C14B—Cl1B | 110.05 (9) |
Cl2A—C14A—D14A | 108.7 | Cl2B—C14B—D14B | 108.7 |
Cl1A—C14A—D14A | 108.7 | Cl3B—C14B—D14B | 108.7 |
Cl3A—C14A—D14A | 108.7 | Cl1B—C14B—D14B | 108.7 |
C7A—N1A—C2A—C10A | 176.12 (12) | C7B—N1B—C2B—C10B | 169.45 (12) |
C7A—N1A—C2A—C3A | −60.94 (16) | C7B—N1B—C2B—C3B | −67.17 (15) |
N1A—C2A—C3A—O12A | −103.50 (14) | N1B—C2B—C3B—O12B | −102.33 (14) |
C10A—C2A—C3A—O12A | 17.19 (17) | C10B—C2B—C3B—O12B | 19.71 (18) |
N1A—C2A—C3A—N4A | 71.16 (13) | N1B—C2B—C3B—N4B | 72.17 (13) |
C10A—C2A—C3A—N4A | −168.15 (11) | C10B—C2B—C3B—N4B | −165.79 (11) |
O12A—C3A—N4A—C5A | 174.51 (13) | O12B—C3B—N4B—C5B | 176.14 (12) |
C2A—C3A—N4A—C5A | −0.14 (17) | C2B—C3B—N4B—C5B | 1.66 (17) |
O12A—C3A—N4A—C13A | 3.66 (19) | O12B—C3B—N4B—C13B | 9.8 (2) |
C2A—C3A—N4A—C13A | −170.99 (11) | C2B—C3B—N4B—C13B | −164.72 (11) |
C3A—N4A—C5A—N6A | −67.95 (16) | C3B—N4B—C5B—N6B | −68.76 (15) |
C13A—N4A—C5A—N6A | 102.86 (13) | C13B—N4B—C5B—N6B | 98.02 (13) |
N4A—C5A—N6A—C7A | 45.31 (18) | N4B—C5B—N6B—C7B | 46.51 (19) |
C5A—N6A—C7A—O8A | −169.28 (12) | C5B—N6B—C7B—O8B | −171.00 (13) |
C5A—N6A—C7A—N1A | 12.43 (19) | C5B—N6B—C7B—N1B | 8.1 (2) |
C2A—N1A—C7A—O8A | 179.10 (12) | C2B—N1B—C7B—O8B | −176.09 (12) |
C2A—N1A—C7A—N6A | −2.58 (19) | C2B—N1B—C7B—N6B | 4.77 (19) |
N1A—C2A—C10A—C9A | −53.89 (14) | N1B—C2B—C10B—C9B | −52.22 (15) |
C3A—C2A—C10A—C9A | −173.10 (11) | C3B—C2B—C10B—C9B | −171.53 (12) |
N1A—C2A—C10A—C11A | −175.93 (11) | N1B—C2B—C10B—C11B | −173.23 (12) |
C3A—C2A—C10A—C11A | 64.86 (15) | C3B—C2B—C10B—C11B | 67.46 (14) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1A—H1A···O8Bi | 0.86 (1) | 2.07 (1) | 2.9012 (15) | 163 (2) |
N1B—H1B···O8Aii | 0.86 (1) | 2.06 (1) | 2.9123 (14) | 174 (2) |
N6A—H6A···O12Biii | 0.85 (1) | 2.13 (1) | 2.9600 (15) | 165 (2) |
N6B—H6B···O12Aiv | 0.86 (1) | 2.14 (1) | 2.9239 (14) | 153 (2) |
C13B—H13E···O8Bv | 0.98 | 2.50 | 3.4100 (17) | 154 |
C13A—H13B···O8Avi | 0.98 | 2.42 | 3.3256 (17) | 154 |
C5A—H51A···O8Avi | 0.99 | 2.55 | 3.4071 (16) | 145 |
C14A—D14A···O8Bi | 1.00 | 2.36 | 3.2024 (18) | 142 |
Symmetry codes: (i) x−1, y, z; (ii) x+1, y, z; (iii) x−1/2, −y+1/2, −z+1; (iv) x+1/2, −y+3/2, −z+1; (v) x−1/2, −y+3/2, −z+1; (vi) x+1/2, −y+1/2, −z+1. |
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