The stereochemistry of the title compound, C39H32ClN7O4, shows that the 3a-methyl and 4a-phenyl groups possess a trans conformation and have opposite configurations, viz. S,R or R,S.
Supporting information
CCDC reference: 642967
Key indicators
- Single-crystal X-ray study
- T = 295 K
- Mean (C-C) = 0.005 Å
- R factor = 0.075
- wR factor = 0.190
- Data-to-parameter ratio = 13.3
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT242_ALERT_2_B Check Low Ueq as Compared to Neighbors for C37
Alert level C
PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.13 Ratio
PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.74 Ratio
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for N7
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C21
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5
PLAT360_ALERT_2_C Short C(sp3)-C(sp3) Bond C38 - C39 ... 1.43 Ang.
0 ALERT level A = In general: serious problem
1 ALERT level B = Potentially serious problem
6 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
5 ALERT type 2 Indicator that the structure model may be wrong or deficient
2 ALERT type 3 Indicator that the structure quality may be low
0 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.
BOUDINA Aicha - student in phD , synthesis of samples
BAOUID Abdesselam -synthesis of samples and contributes to the writing of
the article
HASNAOUI Aissa - contributes to the writing of the article and interpretation
of the results
AATIF Abdeljalil - Bibliographic research and synthesis of samples
EDDIKE Driss - writing the paper (CIF file, Figures)
TILLARD Monique- crystals selection, data collection
and crystal structure determination
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: CrysAlis CCD (Oxford Diffraction, 2004); cell refinement: CrysAlis RED (Oxford Diffraction, 2004); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 pour Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).
rac-Ethyl 7-(4-chlorophenyl)-3a-methyl-3-(4-nitrophenyl)-
4a,5-diphenyl-3a,4a,8,13-tetrahydro-4
H- bis[1,2,4-triazolo][4,3 -
a:3',4'-d][1,5]benzodiazepine-1-carboxylate
top
Crystal data top
C39H32ClN7O4 | F(000) = 1456 |
Mr = 698.17 | Dx = 1.327 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 6144 reflections |
a = 17.3927 (9) Å | θ = 3.2–25.0° |
b = 9.2018 (5) Å | µ = 0.16 mm−1 |
c = 22.846 (1) Å | T = 295 K |
β = 107.102 (5)° | Parallelepiped, orange |
V = 3494.7 (3) Å3 | 0.55 × 0.48 × 0.17 mm |
Z = 4 | |
Data collection top
Oxford Xcalibur CCD diffractometer | 5135 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.057 |
Graphite monochromator | θmax = 25.0°, θmin = 3.2° |
ω scans | h = 0→20 |
59211 measured reflections | k = 0→10 |
6144 independent reflections | l = −27→25 |
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)] = 0.075 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.190 | H-atom parameters constrained |
S = 1.12 | w = 1/[σ2(Fo2) + (0.073P)2 + 3.0925P] where P = (Fo2 + 2Fc2)/3 |
6144 reflections | (Δ/σ)max < 0.001 |
462 parameters | Δρmax = 0.32 e Å−3 |
0 restraints | Δρmin = −0.40 e Å−3 |
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. Some disorder appears at the ethyl group as shown by the high
values of equivalent ADPs for atoms C32 and C33. Despite the lower isotropic
displacement parameters for the atoms, attemps to take into account such a
disorder by splitting (PART instruction of SHELXL) the involved atoms
(C32, C33, O3, O4 and even O1, O2 and Cl) did not improve the overall
refinement. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Cl1 | −0.12141 (7) | 0.0944 (2) | 0.71263 (6) | 0.1356 (7) | |
O1 | 0.3092 (4) | 0.3697 (4) | 0.82507 (14) | 0.167 (2) | |
O2 | 0.32880 (16) | 0.6029 (3) | 0.83280 (10) | 0.0727 (7) | |
O3 | 0.5235 (3) | 0.9240 (4) | 1.24730 (14) | 0.1225 (14) | |
O4 | 0.4763 (3) | 1.0892 (4) | 1.18056 (15) | 0.1249 (14) | |
N1 | 0.17697 (14) | 0.2407 (3) | 1.05111 (11) | 0.0472 (6) | |
N2 | 0.10541 (14) | 0.2030 (3) | 1.00552 (12) | 0.0534 (6) | |
N3 | 0.19951 (13) | 0.2556 (3) | 0.95796 (10) | 0.0426 (5) | |
N4 | 0.37299 (14) | 0.5394 (3) | 1.01583 (10) | 0.0452 (6) | |
N5 | 0.35403 (14) | 0.5876 (3) | 0.95535 (10) | 0.0451 (6) | |
N6 | 0.35053 (15) | 0.3455 (3) | 0.95440 (11) | 0.0490 (6) | |
N7 | 0.4870 (2) | 0.9620 (4) | 1.19538 (15) | 0.0820 (10) | |
C1 | 0.12048 (17) | 0.2068 (3) | 0.95408 (14) | 0.0491 (7) | |
C2 | 0.22629 (16) | 0.3296 (3) | 1.01820 (12) | 0.0402 (6) | |
C3 | 0.31528 (15) | 0.3124 (3) | 1.05140 (12) | 0.0417 (6) | |
H3A | 0.3268 | 0.2094 | 1.0573 | 0.050* | |
H3B | 0.3257 | 0.3558 | 1.0917 | 0.050* | |
C4 | 0.37507 (16) | 0.3785 (3) | 1.02054 (13) | 0.0422 (6) | |
C5 | 0.34018 (16) | 0.4724 (3) | 0.92237 (13) | 0.0447 (7) | |
C6 | 0.32379 (17) | 0.2032 (3) | 0.93408 (13) | 0.0454 (7) | |
C7 | 0.25002 (17) | 0.1561 (3) | 0.93826 (13) | 0.0427 (6) | |
C8 | 0.22593 (19) | 0.0152 (3) | 0.91954 (14) | 0.0523 (7) | |
H8 | 0.1769 | −0.0194 | 0.9223 | 0.063* | |
C9 | 0.2743 (2) | −0.0732 (3) | 0.89690 (15) | 0.0608 (9) | |
H9 | 0.2572 | −0.1666 | 0.8839 | 0.073* | |
C10 | 0.3471 (2) | −0.0256 (4) | 0.89331 (16) | 0.0661 (9) | |
H10 | 0.3793 | −0.0861 | 0.8778 | 0.079* | |
C11 | 0.3726 (2) | 0.1123 (4) | 0.91273 (16) | 0.0612 (9) | |
H11 | 0.4228 | 0.1443 | 0.9115 | 0.073* | |
C12 | 0.16449 (19) | 0.2969 (4) | 1.10572 (14) | 0.0541 (8) | |
C13 | 0.0967 (2) | 0.3747 (5) | 1.10533 (17) | 0.0715 (10) | |
H13 | 0.0555 | 0.3861 | 1.0689 | 0.086* | |
C14 | 0.0895 (3) | 0.4357 (6) | 1.1585 (2) | 0.0983 (15) | |
H14 | 0.0431 | 0.4865 | 1.1579 | 0.118* | |
C15 | 0.1501 (3) | 0.4223 (7) | 1.2123 (2) | 0.1053 (17) | |
H15 | 0.1460 | 0.4676 | 1.2476 | 0.126* | |
C16 | 0.2170 (3) | 0.3415 (6) | 1.21371 (17) | 0.0931 (15) | |
H16 | 0.2574 | 0.3296 | 1.2505 | 0.112* | |
C17 | 0.2248 (2) | 0.2771 (4) | 1.16056 (16) | 0.0710 (10) | |
H17 | 0.2699 | 0.2216 | 1.1618 | 0.085* | |
C18 | 0.06117 (17) | 0.1747 (4) | 0.89508 (15) | 0.0567 (8) | |
C19 | 0.0720 (2) | 0.2306 (4) | 0.84194 (16) | 0.0648 (9) | |
H19 | 0.1179 | 0.2847 | 0.8439 | 0.078* | |
C20 | 0.0150 (2) | 0.2068 (5) | 0.78549 (17) | 0.0754 (11) | |
H20 | 0.0220 | 0.2460 | 0.7499 | 0.091* | |
C21 | −0.0514 (2) | 0.1247 (5) | 0.78342 (19) | 0.0842 (13) | |
C22 | −0.0624 (2) | 0.0644 (6) | 0.8352 (2) | 0.0930 (15) | |
H22 | −0.1072 | 0.0068 | 0.8326 | 0.112* | |
C23 | −0.0063 (2) | 0.0898 (5) | 0.89173 (19) | 0.0762 (11) | |
H23 | −0.0137 | 0.0503 | 0.9271 | 0.091* | |
C24 | 0.19779 (15) | 0.4875 (3) | 1.01197 (12) | 0.0399 (6) | |
C25 | 0.15091 (17) | 0.5444 (3) | 0.95697 (13) | 0.0487 (7) | |
H25 | 0.1395 | 0.4877 | 0.9218 | 0.058* | |
C26 | 0.12069 (19) | 0.6846 (4) | 0.95347 (16) | 0.0596 (8) | |
H26 | 0.0893 | 0.7207 | 0.9161 | 0.072* | |
C27 | 0.1367 (2) | 0.7703 (4) | 1.00460 (17) | 0.0657 (9) | |
H27 | 0.1150 | 0.8632 | 1.0023 | 0.079* | |
C28 | 0.1851 (2) | 0.7179 (4) | 1.05926 (16) | 0.0595 (8) | |
H28 | 0.1976 | 0.7768 | 1.0939 | 0.071* | |
C29 | 0.21539 (19) | 0.5782 (3) | 1.06324 (13) | 0.0504 (7) | |
H29 | 0.2480 | 0.5440 | 1.1006 | 0.060* | |
C30 | 0.45928 (18) | 0.3166 (4) | 1.05014 (16) | 0.0598 (8) | |
H30A | 0.4699 | 0.3147 | 1.0938 | 0.090* | |
H30B | 0.4985 | 0.3767 | 1.0398 | 0.090* | |
H30C | 0.4622 | 0.2197 | 1.0354 | 0.090* | |
C31 | 0.39977 (16) | 0.6408 (3) | 1.06123 (12) | 0.0428 (6) | |
C32 | 0.4338 (2) | 0.6023 (3) | 1.12269 (13) | 0.0552 (8) | |
H32 | 0.4374 | 0.5049 | 1.1341 | 0.066* | |
C33 | 0.4621 (2) | 0.7082 (4) | 1.16622 (14) | 0.0620 (9) | |
H33 | 0.4860 | 0.6826 | 1.2069 | 0.074* | |
C34 | 0.4550 (2) | 0.8516 (3) | 1.14937 (14) | 0.0548 (8) | |
C35 | 0.4191 (2) | 0.8919 (3) | 1.08998 (15) | 0.0565 (8) | |
H35 | 0.4134 | 0.9898 | 1.0795 | 0.068* | |
C36 | 0.39173 (18) | 0.7880 (3) | 1.04606 (14) | 0.0514 (7) | |
H36 | 0.3675 | 0.8156 | 1.0057 | 0.062* | |
C37 | 0.3242 (2) | 0.4751 (4) | 0.85504 (15) | 0.0645 (9) | |
C38 | 0.3181 (3) | 0.6116 (6) | 0.76703 (17) | 0.0971 (15) | |
H38A | 0.3650 | 0.5717 | 0.7580 | 0.116* | |
H38B | 0.2716 | 0.5546 | 0.7451 | 0.116* | |
C39 | 0.3069 (4) | 0.7597 (6) | 0.7471 (2) | 0.125 (2) | |
H39A | 0.2978 | 0.7639 | 0.7036 | 0.187* | |
H39B | 0.3542 | 0.8148 | 0.7672 | 0.187* | |
H39C | 0.2614 | 0.7997 | 0.7571 | 0.187* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cl1 | 0.0736 (7) | 0.2261 (19) | 0.0862 (8) | −0.0016 (9) | −0.0087 (6) | −0.0690 (10) |
O1 | 0.332 (7) | 0.080 (2) | 0.0524 (18) | −0.021 (3) | −0.003 (3) | −0.0129 (17) |
O2 | 0.0951 (19) | 0.0816 (18) | 0.0400 (12) | −0.0116 (14) | 0.0179 (12) | 0.0042 (12) |
O3 | 0.197 (4) | 0.094 (2) | 0.0536 (17) | −0.024 (2) | 0.001 (2) | −0.0189 (16) |
O4 | 0.225 (4) | 0.0615 (19) | 0.080 (2) | −0.020 (2) | 0.031 (2) | −0.0189 (16) |
N1 | 0.0384 (12) | 0.0543 (15) | 0.0484 (14) | −0.0083 (11) | 0.0119 (10) | 0.0047 (11) |
N2 | 0.0418 (13) | 0.0605 (16) | 0.0560 (16) | −0.0106 (12) | 0.0115 (11) | −0.0037 (13) |
N3 | 0.0363 (12) | 0.0466 (13) | 0.0432 (13) | −0.0033 (10) | 0.0091 (10) | −0.0058 (10) |
N4 | 0.0505 (13) | 0.0441 (13) | 0.0391 (12) | −0.0125 (11) | 0.0101 (10) | 0.0014 (10) |
N5 | 0.0447 (13) | 0.0498 (14) | 0.0365 (12) | −0.0075 (11) | 0.0053 (10) | 0.0034 (11) |
N6 | 0.0541 (14) | 0.0489 (15) | 0.0462 (14) | −0.0091 (12) | 0.0181 (11) | −0.0026 (11) |
N7 | 0.125 (3) | 0.065 (2) | 0.059 (2) | −0.016 (2) | 0.032 (2) | −0.0181 (17) |
C1 | 0.0385 (15) | 0.0565 (18) | 0.0536 (18) | −0.0056 (13) | 0.0155 (13) | −0.0040 (14) |
C2 | 0.0400 (14) | 0.0452 (16) | 0.0345 (13) | −0.0042 (12) | 0.0096 (11) | 0.0008 (12) |
C3 | 0.0386 (14) | 0.0401 (15) | 0.0446 (15) | −0.0010 (12) | 0.0092 (12) | 0.0041 (12) |
C4 | 0.0411 (14) | 0.0411 (15) | 0.0435 (15) | −0.0045 (12) | 0.0110 (12) | 0.0022 (12) |
C5 | 0.0354 (14) | 0.0531 (18) | 0.0434 (15) | −0.0052 (13) | 0.0081 (12) | 0.0005 (14) |
C6 | 0.0448 (15) | 0.0419 (16) | 0.0504 (16) | −0.0033 (13) | 0.0156 (13) | −0.0044 (13) |
C7 | 0.0450 (15) | 0.0383 (15) | 0.0447 (15) | −0.0006 (12) | 0.0130 (12) | −0.0013 (12) |
C8 | 0.0526 (17) | 0.0449 (17) | 0.0568 (18) | −0.0060 (14) | 0.0121 (14) | −0.0009 (14) |
C9 | 0.075 (2) | 0.0395 (17) | 0.061 (2) | 0.0052 (16) | 0.0098 (17) | −0.0055 (15) |
C10 | 0.068 (2) | 0.062 (2) | 0.068 (2) | 0.0147 (18) | 0.0188 (18) | −0.0137 (18) |
C11 | 0.0485 (17) | 0.073 (2) | 0.065 (2) | 0.0007 (16) | 0.0225 (16) | −0.0120 (18) |
C12 | 0.0554 (18) | 0.065 (2) | 0.0452 (17) | −0.0130 (16) | 0.0199 (14) | 0.0073 (15) |
C13 | 0.056 (2) | 0.108 (3) | 0.056 (2) | −0.011 (2) | 0.0253 (16) | −0.005 (2) |
C14 | 0.079 (3) | 0.149 (5) | 0.080 (3) | −0.017 (3) | 0.045 (2) | −0.024 (3) |
C15 | 0.109 (4) | 0.150 (5) | 0.072 (3) | −0.040 (4) | 0.050 (3) | −0.021 (3) |
C16 | 0.110 (4) | 0.123 (4) | 0.041 (2) | −0.038 (3) | 0.013 (2) | 0.011 (2) |
C17 | 0.072 (2) | 0.083 (3) | 0.054 (2) | −0.012 (2) | 0.0136 (17) | 0.0213 (19) |
C18 | 0.0381 (15) | 0.071 (2) | 0.0590 (19) | −0.0039 (15) | 0.0109 (14) | −0.0177 (17) |
C19 | 0.0488 (18) | 0.083 (3) | 0.060 (2) | −0.0025 (17) | 0.0112 (15) | −0.0132 (18) |
C20 | 0.060 (2) | 0.106 (3) | 0.057 (2) | 0.008 (2) | 0.0112 (17) | −0.023 (2) |
C21 | 0.049 (2) | 0.124 (4) | 0.071 (3) | 0.004 (2) | 0.0049 (18) | −0.042 (3) |
C22 | 0.046 (2) | 0.133 (4) | 0.094 (3) | −0.020 (2) | 0.011 (2) | −0.041 (3) |
C23 | 0.0455 (19) | 0.105 (3) | 0.078 (2) | −0.0151 (19) | 0.0183 (17) | −0.021 (2) |
C24 | 0.0367 (14) | 0.0437 (15) | 0.0406 (14) | 0.0009 (12) | 0.0134 (11) | 0.0034 (12) |
C25 | 0.0459 (16) | 0.0536 (18) | 0.0443 (16) | 0.0014 (14) | 0.0096 (13) | 0.0062 (14) |
C26 | 0.0539 (18) | 0.059 (2) | 0.062 (2) | 0.0110 (16) | 0.0099 (15) | 0.0149 (17) |
C27 | 0.072 (2) | 0.053 (2) | 0.079 (2) | 0.0185 (17) | 0.0333 (19) | 0.0143 (18) |
C28 | 0.074 (2) | 0.0505 (19) | 0.061 (2) | 0.0052 (16) | 0.0312 (17) | −0.0054 (16) |
C29 | 0.0544 (17) | 0.0555 (18) | 0.0418 (16) | 0.0028 (14) | 0.0148 (13) | 0.0042 (14) |
C30 | 0.0406 (16) | 0.067 (2) | 0.070 (2) | 0.0019 (15) | 0.0130 (15) | 0.0048 (17) |
C31 | 0.0418 (14) | 0.0443 (16) | 0.0406 (15) | −0.0054 (12) | 0.0096 (12) | −0.0004 (12) |
C32 | 0.078 (2) | 0.0437 (17) | 0.0406 (16) | −0.0074 (15) | 0.0116 (15) | 0.0055 (13) |
C33 | 0.081 (2) | 0.064 (2) | 0.0389 (16) | −0.0112 (18) | 0.0138 (15) | 0.0000 (15) |
C34 | 0.068 (2) | 0.0514 (19) | 0.0470 (17) | −0.0076 (15) | 0.0200 (15) | −0.0086 (14) |
C35 | 0.073 (2) | 0.0426 (17) | 0.0559 (19) | −0.0011 (15) | 0.0214 (16) | −0.0014 (14) |
C36 | 0.0571 (18) | 0.0475 (18) | 0.0437 (16) | 0.0003 (14) | 0.0056 (14) | 0.0022 (14) |
C37 | 0.079 (2) | 0.059 (2) | 0.0447 (17) | −0.0061 (18) | 0.0017 (16) | −0.0071 (17) |
C38 | 0.123 (4) | 0.124 (4) | 0.044 (2) | 0.006 (3) | 0.023 (2) | 0.009 (2) |
C39 | 0.190 (6) | 0.120 (4) | 0.066 (3) | −0.027 (4) | 0.041 (3) | 0.024 (3) |
Geometric parameters (Å, º) top
Cl1—C21 | 1.737 (4) | C11—C10 | 1.373 (5) |
O2—C37 | 1.292 (4) | C11—H11 | 0.9300 |
O2—C38 | 1.461 (4) | C35—C34 | 1.367 (4) |
O4—N7 | 1.218 (4) | C35—H35 | 0.9300 |
O3—N7 | 1.220 (4) | C8—C9 | 1.376 (5) |
O1—C37 | 1.172 (4) | C8—C7 | 1.390 (4) |
N4—C31 | 1.371 (4) | C8—H8 | 0.9300 |
N4—N5 | 1.395 (3) | C34—C33 | 1.370 (5) |
N4—C4 | 1.484 (4) | C33—H33 | 0.9300 |
N5—C5 | 1.282 (4) | C9—C10 | 1.365 (5) |
N1—N2 | 1.411 (3) | C9—H9 | 0.9300 |
N1—C12 | 1.425 (4) | C18—C19 | 1.382 (5) |
N1—C2 | 1.533 (3) | C18—C23 | 1.392 (5) |
N2—C1 | 1.278 (4) | C19—C20 | 1.393 (5) |
N7—C34 | 1.451 (4) | C19—H19 | 0.9300 |
C4—N6 | 1.476 (4) | C10—H10 | 0.9300 |
C4—C30 | 1.531 (4) | C28—C27 | 1.372 (5) |
C4—C3 | 1.542 (4) | C28—H28 | 0.9300 |
C2—N3 | 1.483 (3) | C27—C26 | 1.368 (5) |
C2—C3 | 1.518 (4) | C27—H27 | 0.9300 |
C2—C24 | 1.528 (4) | C26—H26 | 0.9300 |
N3—C1 | 1.424 (4) | C30—H30A | 0.9600 |
N3—C7 | 1.430 (4) | C30—H30B | 0.9600 |
N6—C5 | 1.362 (4) | C30—H30C | 0.9600 |
N6—C6 | 1.421 (4) | C13—C14 | 1.376 (5) |
C25—C24 | 1.384 (4) | C13—H13 | 0.9300 |
C25—C26 | 1.386 (4) | C23—C22 | 1.390 (5) |
C25—H25 | 0.9300 | C23—H23 | 0.9300 |
C24—C29 | 1.397 (4) | C21—C20 | 1.370 (6) |
C3—H3A | 0.9700 | C21—C22 | 1.371 (6) |
C3—H3B | 0.9700 | C20—H20 | 0.9300 |
C5—C37 | 1.481 (4) | C17—C16 | 1.393 (6) |
C31—C36 | 1.395 (4) | C17—H17 | 0.9300 |
C31—C32 | 1.400 (4) | C16—C15 | 1.372 (7) |
C12—C13 | 1.378 (5) | C16—H16 | 0.9300 |
C12—C17 | 1.389 (5) | C38—C39 | 1.432 (7) |
C29—C28 | 1.383 (4) | C38—H38A | 0.9700 |
C29—H29 | 0.9300 | C38—H38B | 0.9700 |
C6—C11 | 1.379 (4) | C22—H22 | 0.9300 |
C6—C7 | 1.384 (4) | C14—C15 | 1.369 (7) |
C32—C33 | 1.376 (4) | C14—H14 | 0.9300 |
C32—H32 | 0.9300 | C15—H15 | 0.9300 |
C36—C35 | 1.367 (4) | C39—H39A | 0.9600 |
C36—H36 | 0.9300 | C39—H39B | 0.9600 |
C1—C18 | 1.467 (4) | C39—H39C | 0.9600 |
| | | |
C37—O2—C38 | 116.7 (3) | C33—C34—N7 | 119.2 (3) |
C31—N4—N5 | 117.5 (2) | C34—C33—C32 | 119.7 (3) |
C31—N4—C4 | 128.9 (2) | C34—C33—H33 | 120.1 |
N5—N4—C4 | 112.5 (2) | C32—C33—H33 | 120.1 |
C5—N5—N4 | 105.5 (2) | C6—C7—C8 | 118.2 (3) |
N2—N1—C12 | 114.0 (2) | C6—C7—N3 | 119.2 (2) |
N2—N1—C2 | 105.6 (2) | C8—C7—N3 | 122.4 (3) |
C12—N1—C2 | 119.2 (2) | C10—C9—C8 | 120.9 (3) |
C1—N2—N1 | 107.3 (2) | C10—C9—H9 | 119.5 |
O4—N7—O3 | 122.6 (3) | C8—C9—H9 | 119.5 |
O4—N7—C34 | 118.5 (3) | C19—C18—C23 | 119.4 (3) |
O3—N7—C34 | 118.9 (3) | C19—C18—C1 | 119.5 (3) |
N6—C4—N4 | 97.9 (2) | C23—C18—C1 | 121.1 (3) |
N6—C4—C30 | 109.1 (2) | C18—C19—C20 | 120.7 (3) |
N4—C4—C30 | 113.7 (2) | C18—C19—H19 | 119.6 |
N6—C4—C3 | 110.9 (2) | C20—C19—H19 | 119.6 |
N4—C4—C3 | 114.9 (2) | C9—C10—C11 | 119.6 (3) |
C30—C4—C3 | 109.7 (2) | C9—C10—H10 | 120.2 |
N3—C2—C3 | 114.3 (2) | C11—C10—H10 | 120.2 |
N3—C2—C24 | 110.2 (2) | C27—C28—C29 | 120.4 (3) |
C3—C2—C24 | 113.6 (2) | C27—C28—H28 | 119.8 |
N3—C2—N1 | 98.2 (2) | C29—C28—H28 | 119.8 |
C3—C2—N1 | 109.6 (2) | C26—C27—C28 | 119.4 (3) |
C24—C2—N1 | 109.9 (2) | C26—C27—H27 | 120.3 |
C1—N3—C7 | 116.7 (2) | C28—C27—H27 | 120.3 |
C1—N3—C2 | 103.7 (2) | C27—C26—C25 | 120.5 (3) |
C7—N3—C2 | 122.1 (2) | C27—C26—H26 | 119.7 |
C5—N6—C6 | 129.5 (2) | C25—C26—H26 | 119.7 |
C5—N6—C4 | 109.1 (2) | O1—C37—O2 | 123.5 (3) |
C6—N6—C4 | 119.5 (2) | O1—C37—C5 | 122.3 (4) |
C24—C25—C26 | 121.1 (3) | O2—C37—C5 | 114.2 (3) |
C24—C25—H25 | 119.4 | C4—C30—H30A | 109.5 |
C26—C25—H25 | 119.4 | C4—C30—H30B | 109.5 |
C25—C24—C29 | 117.4 (3) | H30A—C30—H30B | 109.5 |
C25—C24—C2 | 122.2 (3) | C4—C30—H30C | 109.5 |
C29—C24—C2 | 120.3 (2) | H30A—C30—H30C | 109.5 |
C2—C3—C4 | 117.1 (2) | H30B—C30—H30C | 109.5 |
C2—C3—H3A | 108.0 | C14—C13—C12 | 120.3 (4) |
C4—C3—H3A | 108.0 | C14—C13—H13 | 119.8 |
C2—C3—H3B | 108.0 | C12—C13—H13 | 119.8 |
C4—C3—H3B | 108.0 | C22—C23—C18 | 119.7 (4) |
H3A—C3—H3B | 107.3 | C22—C23—H23 | 120.1 |
N5—C5—N6 | 114.9 (2) | C18—C23—H23 | 120.1 |
N5—C5—C37 | 122.8 (3) | C20—C21—C22 | 121.6 (4) |
N6—C5—C37 | 121.8 (3) | C20—C21—Cl1 | 118.3 (4) |
N4—C31—C36 | 119.1 (3) | C22—C21—Cl1 | 120.1 (3) |
N4—C31—C32 | 122.4 (3) | C21—C20—C19 | 118.8 (4) |
C36—C31—C32 | 118.5 (3) | C21—C20—H20 | 120.6 |
C13—C12—C17 | 119.5 (3) | C19—C20—H20 | 120.6 |
C13—C12—N1 | 122.2 (3) | C12—C17—C16 | 119.3 (4) |
C17—C12—N1 | 118.2 (3) | C12—C17—H17 | 120.4 |
C28—C29—C24 | 121.0 (3) | C16—C17—H17 | 120.4 |
C28—C29—H29 | 119.5 | C15—C16—C17 | 120.6 (4) |
C24—C29—H29 | 119.5 | C15—C16—H16 | 119.7 |
C11—C6—C7 | 120.9 (3) | C17—C16—H16 | 119.7 |
C11—C6—N6 | 119.9 (3) | C39—C38—O2 | 110.1 (4) |
C7—C6—N6 | 119.2 (3) | C39—C38—H38A | 109.6 |
C33—C32—C31 | 120.1 (3) | O2—C38—H38A | 109.6 |
C33—C32—H32 | 119.9 | C39—C38—H38B | 109.6 |
C31—C32—H32 | 119.9 | O2—C38—H38B | 109.6 |
C35—C36—C31 | 120.6 (3) | H38A—C38—H38B | 108.2 |
C35—C36—H36 | 119.7 | C21—C22—C23 | 119.7 (4) |
C31—C36—H36 | 119.7 | C21—C22—H22 | 120.2 |
N2—C1—N3 | 114.0 (3) | C23—C22—H22 | 120.2 |
N2—C1—C18 | 124.1 (3) | C15—C14—C13 | 120.7 (5) |
N3—C1—C18 | 121.7 (3) | C15—C14—H14 | 119.7 |
C10—C11—C6 | 120.1 (3) | C13—C14—H14 | 119.7 |
C10—C11—H11 | 119.9 | C14—C15—C16 | 119.6 (4) |
C6—C11—H11 | 119.9 | C14—C15—H15 | 120.2 |
C36—C35—C34 | 119.8 (3) | C16—C15—H15 | 120.2 |
C36—C35—H35 | 120.1 | C38—C39—H39A | 109.5 |
C34—C35—H35 | 120.1 | C38—C39—H39B | 109.5 |
C9—C8—C7 | 120.3 (3) | H39A—C39—H39B | 109.5 |
C9—C8—H8 | 119.9 | C38—C39—H39C | 109.5 |
C7—C8—H8 | 119.9 | H39A—C39—H39C | 109.5 |
C35—C34—C33 | 121.2 (3) | H39B—C39—H39C | 109.5 |
C35—C34—N7 | 119.7 (3) | | |
| | | |
C31—N4—N5—C5 | 172.5 (2) | C32—C31—C36—C35 | 2.3 (5) |
C4—N4—N5—C5 | 3.3 (3) | N1—N2—C1—N3 | −4.0 (4) |
C12—N1—N2—C1 | 156.5 (3) | N1—N2—C1—C18 | −179.7 (3) |
C2—N1—N2—C1 | 23.8 (3) | C7—N3—C1—N2 | 119.4 (3) |
C31—N4—C4—N6 | −170.5 (3) | C2—N3—C1—N2 | −17.9 (3) |
N5—N4—C4—N6 | −2.8 (3) | C7—N3—C1—C18 | −64.8 (4) |
C31—N4—C4—C30 | −55.6 (4) | C2—N3—C1—C18 | 157.9 (3) |
N5—N4—C4—C30 | 112.1 (3) | C7—C6—C11—C10 | 2.2 (5) |
C31—N4—C4—C3 | 72.0 (4) | N6—C6—C11—C10 | 179.7 (3) |
N5—N4—C4—C3 | −120.2 (2) | C31—C36—C35—C34 | 0.1 (5) |
N2—N1—C2—N3 | −32.5 (3) | C36—C35—C34—C33 | −1.8 (5) |
C12—N1—C2—N3 | −162.2 (2) | C36—C35—C34—N7 | 177.4 (3) |
N2—N1—C2—C3 | −152.0 (2) | O4—N7—C34—C35 | 4.9 (6) |
C12—N1—C2—C3 | 78.3 (3) | O3—N7—C34—C35 | −175.2 (4) |
N2—N1—C2—C24 | 82.5 (3) | O4—N7—C34—C33 | −176.0 (4) |
C12—N1—C2—C24 | −47.2 (3) | O3—N7—C34—C33 | 4.0 (6) |
C3—C2—N3—C1 | 144.9 (2) | C35—C34—C33—C32 | 0.9 (5) |
C24—C2—N3—C1 | −85.7 (3) | N7—C34—C33—C32 | −178.3 (3) |
N1—C2—N3—C1 | 29.0 (3) | C31—C32—C33—C34 | 1.6 (5) |
C3—C2—N3—C7 | 10.5 (4) | C11—C6—C7—C8 | −0.9 (4) |
C24—C2—N3—C7 | 139.9 (2) | N6—C6—C7—C8 | −178.4 (3) |
N1—C2—N3—C7 | −105.3 (3) | C11—C6—C7—N3 | −177.1 (3) |
N4—C4—N6—C5 | 1.4 (3) | N6—C6—C7—N3 | 5.3 (4) |
C30—C4—N6—C5 | −117.2 (3) | C9—C8—C7—C6 | −0.7 (4) |
C3—C4—N6—C5 | 121.9 (2) | C9—C8—C7—N3 | 175.4 (3) |
N4—C4—N6—C6 | −164.1 (2) | C1—N3—C7—C6 | 172.4 (3) |
C30—C4—N6—C6 | 77.3 (3) | C2—N3—C7—C6 | −58.7 (4) |
C3—C4—N6—C6 | −43.6 (3) | C1—N3—C7—C8 | −3.7 (4) |
C26—C25—C24—C29 | −1.9 (4) | C2—N3—C7—C8 | 125.2 (3) |
C26—C25—C24—C2 | 175.0 (3) | C7—C8—C9—C10 | 1.1 (5) |
N3—C2—C24—C25 | 2.5 (3) | N2—C1—C18—C19 | 156.4 (3) |
C3—C2—C24—C25 | 132.2 (3) | N3—C1—C18—C19 | −19.0 (5) |
N1—C2—C24—C25 | −104.6 (3) | N2—C1—C18—C23 | −23.0 (5) |
N3—C2—C24—C29 | 179.3 (2) | N3—C1—C18—C23 | 161.6 (3) |
C3—C2—C24—C29 | −50.9 (3) | C23—C18—C19—C20 | 2.0 (5) |
N1—C2—C24—C29 | 72.2 (3) | C1—C18—C19—C20 | −177.4 (3) |
N3—C2—C3—C4 | 63.5 (3) | C8—C9—C10—C11 | 0.2 (5) |
C24—C2—C3—C4 | −64.1 (3) | C6—C11—C10—C9 | −1.8 (5) |
N1—C2—C3—C4 | 172.6 (2) | C24—C29—C28—C27 | 0.2 (5) |
N6—C4—C3—C2 | −44.0 (3) | C29—C28—C27—C26 | −2.1 (5) |
N4—C4—C3—C2 | 65.8 (3) | C28—C27—C26—C25 | 1.9 (5) |
C30—C4—C3—C2 | −164.6 (3) | C24—C25—C26—C27 | 0.1 (5) |
N4—N5—C5—N6 | −2.3 (3) | C38—O2—C37—O1 | −2.9 (7) |
N4—N5—C5—C37 | −174.8 (3) | C38—O2—C37—C5 | 176.7 (3) |
C6—N6—C5—N5 | 164.1 (3) | N5—C5—C37—O1 | −177.6 (5) |
C4—N6—C5—N5 | 0.5 (3) | N6—C5—C37—O1 | 10.3 (6) |
C6—N6—C5—C37 | −23.3 (5) | N5—C5—C37—O2 | 2.7 (5) |
C4—N6—C5—C37 | 173.1 (3) | N6—C5—C37—O2 | −169.4 (3) |
N5—N4—C31—C36 | 12.7 (4) | C17—C12—C13—C14 | 1.7 (6) |
C4—N4—C31—C36 | 179.9 (3) | N1—C12—C13—C14 | −175.4 (4) |
N5—N4—C31—C32 | −168.4 (3) | C19—C18—C23—C22 | −1.0 (6) |
C4—N4—C31—C32 | −1.2 (5) | C1—C18—C23—C22 | 178.4 (4) |
N2—N1—C12—C13 | −31.1 (4) | C22—C21—C20—C19 | −0.8 (6) |
C2—N1—C12—C13 | 94.8 (4) | Cl1—C21—C20—C19 | −179.3 (3) |
N2—N1—C12—C17 | 151.8 (3) | C18—C19—C20—C21 | −1.1 (6) |
C2—N1—C12—C17 | −82.4 (4) | C13—C12—C17—C16 | −2.6 (5) |
C25—C24—C29—C28 | 1.8 (4) | N1—C12—C17—C16 | 174.6 (3) |
C2—C24—C29—C28 | −175.2 (3) | C12—C17—C16—C15 | 0.7 (6) |
C5—N6—C6—C11 | 91.0 (4) | C37—O2—C38—C39 | 167.3 (4) |
C4—N6—C6—C11 | −106.8 (3) | C20—C21—C22—C23 | 1.8 (7) |
C5—N6—C6—C7 | −91.5 (4) | Cl1—C21—C22—C23 | −179.7 (3) |
C4—N6—C6—C7 | 70.7 (4) | C18—C23—C22—C21 | −0.9 (7) |
N4—C31—C32—C33 | 177.9 (3) | C12—C13—C14—C15 | 1.1 (7) |
C36—C31—C32—C33 | −3.2 (5) | C13—C14—C15—C16 | −3.0 (8) |
N4—C31—C36—C35 | −178.8 (3) | C17—C16—C15—C14 | 2.1 (7) |