Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806018629/fl2024sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806018629/fl2024Isup2.hkl |
CCDC reference: 610766
Key indicators
- Single-crystal X-ray study
- T = 294 K
- Mean (C-C) = 0.004 Å
- R factor = 0.050
- wR factor = 0.146
- Data-to-parameter ratio = 13.6
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C19 PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety C8
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 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 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Bruker, 1999); cell refinement: SMART; data reduction: SAINT (Bruker,1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1999); software used to prepare material for publication: SHELXTL.
C18H18ClN5O2 | Z = 4 |
Mr = 371.82 | F(000) = 776 |
Triclinic, P1 | Dx = 1.330 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 8.217 (2) Å | Cell parameters from 2954 reflections |
b = 8.4391 (15) Å | θ = 2.7–23.3° |
c = 30.674 (5) Å | µ = 0.23 mm−1 |
α = 93.15 (1)° | T = 294 K |
β = 90.342 (3)° | Block, colorless |
γ = 118.958 (3)° | 0.50 × 0.30 × 0.20 mm |
V = 1857.0 (6) Å3 |
Bruker SMART CCD area-detector diffractometer | 6481 independent reflections |
Radiation source: fine-focus sealed tube | 4096 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.026 |
φ and ω scans | θmax = 25.0°, θmin = 0.7° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −9→8 |
Tmin = 0.895, Tmax = 0.956 | k = −10→9 |
9445 measured reflections | l = −36→36 |
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)] = 0.050 | H-atom parameters constrained |
wR(F2) = 0.146 | w = 1/[σ2(Fo2) + (0.0725P)2 + 0.178P] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max = 0.003 |
6481 reflections | Δρmax = 0.36 e Å−3 |
478 parameters | Δρmin = −0.41 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: 0.0153 (15) |
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 | 0.51047 (14) | −0.49841 (11) | 0.39047 (3) | 0.0877 (3) | |
Cl2 | 1.01971 (16) | −0.00577 (15) | 0.10191 (3) | 0.0924 (4) | |
O1 | 0.8097 (3) | 0.1268 (2) | 0.35789 (6) | 0.0572 (5) | |
O2 | 1.2226 (3) | 0.7954 (3) | 0.39136 (6) | 0.0516 (5) | |
O3 | 0.6676 (3) | 0.2922 (3) | 0.14041 (6) | 0.0600 (6) | |
O4 | 0.4006 (3) | 0.7109 (2) | 0.11986 (6) | 0.0596 (6) | |
N1 | 0.4050 (3) | −0.3894 (3) | 0.32449 (8) | 0.0561 (6) | |
N2 | 0.6599 (3) | −0.1664 (3) | 0.36949 (7) | 0.0501 (6) | |
N3 | 0.8081 (4) | 0.2701 (3) | 0.33422 (7) | 0.0546 (6) | |
N4 | 1.0988 (4) | 0.8888 (3) | 0.33576 (7) | 0.0527 (6) | |
N5 | 0.9751 (4) | 0.8205 (3) | 0.30058 (7) | 0.0567 (7) | |
N6 | 0.8249 (4) | −0.0782 (3) | 0.17097 (8) | 0.0590 (7) | |
N7 | 0.8242 (3) | 0.1444 (3) | 0.12630 (7) | 0.0512 (6) | |
N8 | 0.5251 (4) | 0.3016 (3) | 0.16579 (7) | 0.0548 (6) | |
N9 | 0.1872 (4) | 0.6013 (3) | 0.17538 (8) | 0.0566 (7) | |
N10 | 0.1335 (4) | 0.4805 (3) | 0.20755 (7) | 0.0575 (7) | |
C1 | 0.5267 (4) | −0.3321 (4) | 0.35717 (9) | 0.0509 (7) | |
C2 | 0.4193 (4) | −0.2547 (4) | 0.30039 (9) | 0.0569 (8) | |
H2 | 0.3369 | −0.2850 | 0.2766 | 0.068* | |
C3 | 0.5482 (4) | −0.0761 (4) | 0.30896 (8) | 0.0505 (7) | |
H3 | 0.5543 | 0.0149 | 0.2921 | 0.061* | |
C4 | 0.6689 (4) | −0.0399 (3) | 0.34433 (8) | 0.0438 (7) | |
C5 | 0.9364 (4) | 0.4201 (4) | 0.35133 (9) | 0.0491 (7) | |
H5 | 1.0102 | 0.4178 | 0.3741 | 0.059* | |
C6 | 0.9725 (4) | 0.5930 (3) | 0.33697 (8) | 0.0437 (7) | |
C7 | 0.8990 (4) | 0.6412 (4) | 0.30152 (8) | 0.0478 (7) | |
C8 | 0.7566 (5) | 0.5202 (4) | 0.26745 (10) | 0.0692 (9) | |
H8A | 0.7343 | 0.5926 | 0.2477 | 0.104* | |
H8B | 0.6429 | 0.4420 | 0.2811 | 0.104* | |
H8C | 0.8007 | 0.4482 | 0.2516 | 0.104* | |
C9 | 1.2091 (5) | 1.0839 (4) | 0.34618 (11) | 0.0743 (10) | |
H9A | 1.2646 | 1.1058 | 0.3750 | 0.111* | |
H9B | 1.1302 | 1.1382 | 0.3449 | 0.111* | |
H9C | 1.3052 | 1.1361 | 0.3255 | 0.111* | |
C10 | 1.0995 (4) | 0.7572 (3) | 0.35770 (8) | 0.0425 (6) | |
C11 | 1.1571 (4) | 0.7780 (3) | 0.43404 (8) | 0.0405 (6) | |
C12 | 1.2726 (4) | 0.7712 (3) | 0.46568 (8) | 0.0445 (7) | |
H12 | 1.3835 | 0.7743 | 0.4581 | 0.053* | |
C13 | 1.2223 (4) | 0.7597 (4) | 0.50890 (9) | 0.0472 (7) | |
C14 | 1.3464 (5) | 0.7530 (5) | 0.54446 (10) | 0.0671 (9) | |
H14A | 1.4718 | 0.8052 | 0.5349 | 0.101* | |
H14B | 1.3035 | 0.6290 | 0.5508 | 0.101* | |
H14C | 1.3425 | 0.8203 | 0.5703 | 0.101* | |
C15 | 1.0546 (4) | 0.7529 (4) | 0.51870 (9) | 0.0525 (7) | |
H15 | 1.0193 | 0.7435 | 0.5476 | 0.063* | |
C16 | 0.9380 (4) | 0.7595 (4) | 0.48698 (9) | 0.0494 (7) | |
C17 | 0.7566 (4) | 0.7526 (5) | 0.49872 (11) | 0.0700 (9) | |
H17A | 0.6606 | 0.6283 | 0.4990 | 0.105* | |
H17B | 0.7234 | 0.8126 | 0.4775 | 0.105* | |
H17C | 0.7703 | 0.8123 | 0.5271 | 0.105* | |
C18 | 0.9913 (4) | 0.7731 (3) | 0.44373 (8) | 0.0449 (7) | |
H18 | 0.9162 | 0.7788 | 0.4218 | 0.054* | |
C19 | 0.8722 (4) | 0.0238 (4) | 0.13744 (9) | 0.0510 (7) | |
C20 | 0.7119 (5) | −0.0473 (4) | 0.19779 (9) | 0.0623 (9) | |
H20 | 0.6748 | −0.1118 | 0.2228 | 0.075* | |
C21 | 0.6488 (4) | 0.0720 (4) | 0.19063 (9) | 0.0536 (8) | |
H21 | 0.5692 | 0.0886 | 0.2095 | 0.064* | |
C22 | 0.7111 (4) | 0.1665 (4) | 0.15354 (8) | 0.0452 (7) | |
C23 | 0.4959 (4) | 0.4246 (4) | 0.15097 (9) | 0.0510 (7) | |
H23 | 0.5667 | 0.4894 | 0.1282 | 0.061* | |
C24 | 0.3580 (4) | 0.4664 (4) | 0.16811 (8) | 0.0444 (7) | |
C25 | 0.2358 (4) | 0.3993 (4) | 0.20276 (8) | 0.0470 (7) | |
C26 | 0.2151 (5) | 0.2594 (4) | 0.23331 (9) | 0.0626 (9) | |
H26A | 0.1189 | 0.2412 | 0.2533 | 0.094* | |
H26B | 0.3305 | 0.2997 | 0.2494 | 0.094* | |
H26C | 0.1824 | 0.1472 | 0.2169 | 0.094* | |
C27 | 0.1006 (6) | 0.7148 (5) | 0.17064 (13) | 0.0889 (12) | |
H27A | 0.1854 | 0.8237 | 0.1573 | 0.133* | |
H27B | 0.0704 | 0.7457 | 0.1989 | 0.133* | |
H27C | −0.0109 | 0.6499 | 0.1526 | 0.133* | |
C28 | 0.3197 (4) | 0.5947 (4) | 0.15181 (8) | 0.0476 (7) | |
C29 | 0.3528 (4) | 0.6416 (3) | 0.07602 (8) | 0.0441 (7) | |
C30 | 0.4723 (4) | 0.7493 (4) | 0.04592 (9) | 0.0481 (7) | |
H30 | 0.5769 | 0.8581 | 0.0550 | 0.058* | |
C31 | 0.4361 (4) | 0.6951 (4) | 0.00190 (9) | 0.0481 (7) | |
C32 | 0.5628 (5) | 0.8117 (5) | −0.03216 (10) | 0.0700 (9) | |
H32A | 0.6436 | 0.9314 | −0.0192 | 0.105* | |
H32B | 0.4894 | 0.8187 | −0.0557 | 0.105* | |
H32C | 0.6363 | 0.7591 | −0.0433 | 0.105* | |
C33 | 0.2784 (4) | 0.5310 (4) | −0.01017 (9) | 0.0506 (7) | |
H33 | 0.2536 | 0.4929 | −0.0396 | 0.061* | |
C34 | 0.1568 (4) | 0.4221 (3) | 0.02006 (9) | 0.0462 (7) | |
C35 | −0.0120 (4) | 0.2462 (4) | 0.00598 (10) | 0.0631 (9) | |
H35A | −0.0676 | 0.2609 | −0.0200 | 0.095* | |
H35B | −0.1001 | 0.2107 | 0.0288 | 0.095* | |
H35C | 0.0234 | 0.1543 | 0.0002 | 0.095* | |
C36 | 0.1955 (4) | 0.4809 (3) | 0.06414 (9) | 0.0468 (7) | |
H36 | 0.1155 | 0.4122 | 0.0853 | 0.056* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0952 (8) | 0.0398 (5) | 0.1055 (7) | 0.0148 (5) | −0.0260 (6) | 0.0097 (4) |
Cl2 | 0.1287 (9) | 0.1304 (9) | 0.0752 (6) | 0.1043 (8) | 0.0464 (6) | 0.0396 (6) |
O1 | 0.0581 (13) | 0.0368 (11) | 0.0645 (12) | 0.0134 (10) | −0.0069 (10) | 0.0045 (9) |
O2 | 0.0416 (11) | 0.0623 (12) | 0.0399 (10) | 0.0166 (10) | 0.0050 (9) | 0.0013 (9) |
O3 | 0.0781 (15) | 0.0690 (14) | 0.0553 (12) | 0.0521 (13) | 0.0185 (11) | 0.0158 (10) |
O4 | 0.0818 (16) | 0.0441 (11) | 0.0438 (11) | 0.0237 (11) | −0.0079 (11) | 0.0019 (9) |
N1 | 0.0547 (16) | 0.0485 (14) | 0.0549 (15) | 0.0181 (13) | −0.0008 (13) | −0.0083 (12) |
N2 | 0.0493 (15) | 0.0366 (13) | 0.0558 (14) | 0.0145 (12) | −0.0040 (12) | −0.0013 (11) |
N3 | 0.0616 (17) | 0.0399 (14) | 0.0570 (15) | 0.0202 (13) | 0.0009 (13) | 0.0057 (11) |
N4 | 0.0617 (17) | 0.0403 (13) | 0.0502 (14) | 0.0202 (13) | 0.0032 (12) | 0.0009 (11) |
N5 | 0.0659 (18) | 0.0535 (16) | 0.0489 (14) | 0.0276 (14) | −0.0033 (13) | 0.0027 (11) |
N6 | 0.0783 (19) | 0.0635 (16) | 0.0476 (14) | 0.0434 (15) | 0.0100 (13) | 0.0122 (12) |
N7 | 0.0636 (17) | 0.0585 (15) | 0.0433 (13) | 0.0381 (14) | 0.0109 (12) | 0.0121 (11) |
N8 | 0.0637 (17) | 0.0608 (15) | 0.0520 (14) | 0.0397 (14) | 0.0067 (13) | 0.0029 (12) |
N9 | 0.0709 (18) | 0.0597 (16) | 0.0541 (14) | 0.0434 (15) | −0.0030 (13) | 0.0027 (12) |
N10 | 0.0669 (18) | 0.0655 (16) | 0.0507 (14) | 0.0405 (15) | 0.0042 (13) | 0.0044 (12) |
C1 | 0.0474 (18) | 0.0410 (17) | 0.0583 (18) | 0.0174 (15) | −0.0007 (15) | −0.0030 (13) |
C2 | 0.056 (2) | 0.064 (2) | 0.0404 (15) | 0.0223 (17) | −0.0039 (14) | −0.0088 (15) |
C3 | 0.0569 (19) | 0.0524 (18) | 0.0384 (15) | 0.0235 (16) | 0.0071 (14) | 0.0025 (13) |
C4 | 0.0432 (17) | 0.0391 (15) | 0.0452 (15) | 0.0171 (14) | 0.0063 (13) | −0.0007 (12) |
C5 | 0.0462 (18) | 0.0462 (17) | 0.0489 (16) | 0.0175 (15) | 0.0052 (14) | 0.0045 (13) |
C6 | 0.0421 (17) | 0.0388 (15) | 0.0440 (15) | 0.0146 (14) | 0.0080 (13) | 0.0034 (12) |
C7 | 0.0469 (18) | 0.0504 (18) | 0.0423 (15) | 0.0213 (15) | 0.0015 (13) | −0.0022 (13) |
C8 | 0.071 (2) | 0.070 (2) | 0.0595 (19) | 0.0301 (19) | −0.0120 (17) | −0.0123 (16) |
C9 | 0.084 (3) | 0.0417 (18) | 0.084 (2) | 0.0206 (18) | −0.002 (2) | 0.0019 (16) |
C10 | 0.0402 (16) | 0.0420 (15) | 0.0409 (15) | 0.0165 (14) | 0.0063 (13) | 0.0018 (12) |
C11 | 0.0389 (16) | 0.0330 (14) | 0.0412 (15) | 0.0109 (13) | 0.0074 (13) | 0.0010 (11) |
C12 | 0.0391 (16) | 0.0437 (16) | 0.0516 (17) | 0.0205 (14) | 0.0081 (14) | 0.0044 (12) |
C13 | 0.0486 (18) | 0.0465 (16) | 0.0481 (16) | 0.0239 (14) | 0.0071 (14) | 0.0075 (13) |
C14 | 0.069 (2) | 0.086 (2) | 0.0565 (18) | 0.044 (2) | 0.0072 (17) | 0.0189 (17) |
C15 | 0.055 (2) | 0.0575 (18) | 0.0426 (15) | 0.0253 (16) | 0.0092 (15) | 0.0066 (13) |
C16 | 0.0399 (17) | 0.0429 (16) | 0.0582 (18) | 0.0147 (14) | 0.0099 (14) | −0.0011 (13) |
C17 | 0.049 (2) | 0.088 (2) | 0.072 (2) | 0.0328 (19) | 0.0114 (17) | −0.0043 (18) |
C18 | 0.0389 (16) | 0.0439 (16) | 0.0450 (15) | 0.0150 (13) | −0.0010 (13) | −0.0008 (12) |
C19 | 0.058 (2) | 0.0592 (18) | 0.0425 (15) | 0.0340 (17) | 0.0058 (14) | 0.0055 (14) |
C20 | 0.084 (2) | 0.069 (2) | 0.0481 (17) | 0.046 (2) | 0.0195 (17) | 0.0214 (15) |
C21 | 0.070 (2) | 0.0554 (18) | 0.0427 (16) | 0.0352 (17) | 0.0133 (15) | 0.0057 (13) |
C22 | 0.0549 (18) | 0.0438 (15) | 0.0399 (15) | 0.0264 (15) | −0.0013 (14) | 0.0014 (12) |
C23 | 0.063 (2) | 0.0488 (17) | 0.0440 (15) | 0.0292 (16) | 0.0026 (14) | 0.0038 (13) |
C24 | 0.0555 (18) | 0.0462 (16) | 0.0368 (14) | 0.0295 (15) | −0.0037 (13) | −0.0029 (12) |
C25 | 0.0551 (18) | 0.0470 (16) | 0.0398 (15) | 0.0266 (15) | −0.0082 (14) | −0.0060 (12) |
C26 | 0.073 (2) | 0.064 (2) | 0.0519 (17) | 0.0333 (19) | −0.0017 (16) | 0.0119 (15) |
C27 | 0.102 (3) | 0.087 (3) | 0.113 (3) | 0.073 (3) | 0.002 (2) | 0.014 (2) |
C28 | 0.061 (2) | 0.0404 (16) | 0.0392 (15) | 0.0230 (15) | −0.0069 (14) | −0.0026 (12) |
C29 | 0.0583 (19) | 0.0400 (15) | 0.0400 (14) | 0.0288 (15) | −0.0057 (14) | 0.0016 (12) |
C30 | 0.0452 (17) | 0.0401 (15) | 0.0575 (18) | 0.0195 (14) | −0.0038 (14) | 0.0038 (13) |
C31 | 0.0498 (18) | 0.0490 (17) | 0.0510 (17) | 0.0280 (15) | 0.0052 (14) | 0.0072 (13) |
C32 | 0.069 (2) | 0.073 (2) | 0.063 (2) | 0.0299 (19) | 0.0113 (18) | 0.0082 (17) |
C33 | 0.060 (2) | 0.0532 (17) | 0.0440 (15) | 0.0327 (17) | −0.0019 (15) | −0.0022 (13) |
C34 | 0.0553 (18) | 0.0391 (15) | 0.0483 (16) | 0.0266 (14) | −0.0060 (14) | 0.0003 (13) |
C35 | 0.068 (2) | 0.0476 (18) | 0.0647 (19) | 0.0211 (17) | −0.0113 (17) | −0.0018 (15) |
C36 | 0.0555 (19) | 0.0369 (15) | 0.0482 (16) | 0.0221 (15) | −0.0002 (14) | 0.0066 (12) |
Cl1—C1 | 1.735 (3) | C12—H12 | 0.9300 |
Cl2—C19 | 1.731 (3) | C13—C15 | 1.386 (4) |
O1—C4 | 1.358 (3) | C13—C14 | 1.511 (4) |
O1—N3 | 1.450 (3) | C14—H14A | 0.9600 |
O2—C10 | 1.352 (3) | C14—H14B | 0.9600 |
O2—C11 | 1.406 (3) | C14—H14C | 0.9600 |
O3—C22 | 1.352 (3) | C15—C16 | 1.383 (4) |
O3—N8 | 1.441 (3) | C15—H15 | 0.9300 |
O4—C28 | 1.359 (3) | C16—C18 | 1.393 (4) |
O4—C29 | 1.410 (3) | C16—C17 | 1.510 (4) |
N1—C1 | 1.306 (4) | C17—H17A | 0.9600 |
N1—C2 | 1.347 (4) | C17—H17B | 0.9600 |
N2—C1 | 1.323 (3) | C17—H17C | 0.9600 |
N2—C4 | 1.325 (3) | C18—H18 | 0.9300 |
N3—C5 | 1.272 (3) | C20—C21 | 1.364 (4) |
N4—C10 | 1.332 (3) | C20—H20 | 0.9300 |
N4—N5 | 1.371 (3) | C21—C22 | 1.380 (4) |
N4—C9 | 1.459 (4) | C21—H21 | 0.9300 |
N5—C7 | 1.331 (3) | C23—C24 | 1.435 (4) |
N6—C19 | 1.314 (3) | C23—H23 | 0.9300 |
N6—C20 | 1.351 (4) | C24—C28 | 1.381 (4) |
N7—C19 | 1.317 (3) | C24—C25 | 1.410 (4) |
N7—C22 | 1.325 (3) | C25—C26 | 1.494 (4) |
N8—C23 | 1.278 (3) | C26—H26A | 0.9600 |
N9—C28 | 1.332 (4) | C26—H26B | 0.9600 |
N9—N10 | 1.374 (3) | C26—H26C | 0.9600 |
N9—C27 | 1.456 (4) | C27—H27A | 0.9600 |
N10—C25 | 1.321 (3) | C27—H27B | 0.9600 |
C2—C3 | 1.368 (4) | C27—H27C | 0.9600 |
C2—H2 | 0.9300 | C29—C30 | 1.372 (4) |
C3—C4 | 1.382 (4) | C29—C36 | 1.373 (4) |
C3—H3 | 0.9300 | C30—C31 | 1.384 (4) |
C5—C6 | 1.437 (4) | C30—H30 | 0.9300 |
C5—H5 | 0.9300 | C31—C33 | 1.391 (4) |
C6—C10 | 1.382 (4) | C31—C32 | 1.509 (4) |
C6—C7 | 1.411 (4) | C32—H32A | 0.9600 |
C7—C8 | 1.488 (4) | C32—H32B | 0.9600 |
C8—H8A | 0.9600 | C32—H32C | 0.9600 |
C8—H8B | 0.9600 | C33—C34 | 1.385 (4) |
C8—H8C | 0.9600 | C33—H33 | 0.9300 |
C9—H9A | 0.9600 | C34—C36 | 1.394 (4) |
C9—H9B | 0.9600 | C34—C35 | 1.498 (4) |
C9—H9C | 0.9600 | C35—H35A | 0.9600 |
C11—C12 | 1.376 (4) | C35—H35B | 0.9600 |
C11—C18 | 1.377 (4) | C35—H35C | 0.9600 |
C12—C13 | 1.385 (4) | C36—H36 | 0.9300 |
C4—O1—N3 | 112.4 (2) | C16—C17—H17A | 109.5 |
C10—O2—C11 | 118.1 (2) | C16—C17—H17B | 109.5 |
C22—O3—N8 | 112.9 (2) | H17A—C17—H17B | 109.5 |
C28—O4—C29 | 118.1 (2) | C16—C17—H17C | 109.5 |
C1—N1—C2 | 113.1 (2) | H17A—C17—H17C | 109.5 |
C1—N2—C4 | 113.8 (2) | H17B—C17—H17C | 109.5 |
C5—N3—O1 | 107.2 (2) | C11—C18—C16 | 118.9 (3) |
C10—N4—N5 | 111.8 (2) | C11—C18—H18 | 120.5 |
C10—N4—C9 | 127.0 (3) | C16—C18—H18 | 120.5 |
N5—N4—C9 | 121.2 (2) | N6—C19—N7 | 130.3 (3) |
C7—N5—N4 | 104.8 (2) | N6—C19—Cl2 | 115.1 (2) |
C19—N6—C20 | 112.4 (2) | N7—C19—Cl2 | 114.6 (2) |
C19—N7—C22 | 114.4 (2) | N6—C20—C21 | 124.4 (3) |
C23—N8—O3 | 107.8 (2) | N6—C20—H20 | 117.8 |
C28—N9—N10 | 111.1 (2) | C21—C20—H20 | 117.8 |
C28—N9—C27 | 128.7 (3) | C20—C21—C22 | 115.4 (3) |
N10—N9—C27 | 120.3 (3) | C20—C21—H21 | 122.3 |
C25—N10—N9 | 105.1 (2) | C22—C21—H21 | 122.3 |
N1—C1—N2 | 130.4 (3) | N7—C22—O3 | 111.5 (2) |
N1—C1—Cl1 | 115.3 (2) | N7—C22—C21 | 123.1 (3) |
N2—C1—Cl1 | 114.3 (2) | O3—C22—C21 | 125.4 (3) |
N1—C2—C3 | 123.7 (3) | N8—C23—C24 | 122.5 (3) |
N1—C2—H2 | 118.1 | N8—C23—H23 | 118.7 |
C3—C2—H2 | 118.1 | C24—C23—H23 | 118.7 |
C2—C3—C4 | 115.5 (3) | C28—C24—C25 | 103.9 (2) |
C2—C3—H3 | 122.3 | C28—C24—C23 | 123.7 (3) |
C4—C3—H3 | 122.3 | C25—C24—C23 | 132.4 (2) |
N2—C4—O1 | 111.5 (2) | N10—C25—C24 | 111.6 (2) |
N2—C4—C3 | 123.4 (3) | N10—C25—C26 | 119.6 (3) |
O1—C4—C3 | 125.2 (3) | C24—C25—C26 | 128.8 (3) |
N3—C5—C6 | 122.9 (3) | C25—C26—H26A | 109.5 |
N3—C5—H5 | 118.6 | C25—C26—H26B | 109.5 |
C6—C5—H5 | 118.6 | H26A—C26—H26B | 109.5 |
C10—C6—C7 | 104.3 (2) | C25—C26—H26C | 109.5 |
C10—C6—C5 | 123.6 (3) | H26A—C26—H26C | 109.5 |
C7—C6—C5 | 132.1 (3) | H26B—C26—H26C | 109.5 |
N5—C7—C6 | 111.3 (2) | N9—C27—H27A | 109.5 |
N5—C7—C8 | 120.0 (3) | N9—C27—H27B | 109.5 |
C6—C7—C8 | 128.6 (3) | H27A—C27—H27B | 109.5 |
C7—C8—H8A | 109.5 | N9—C27—H27C | 109.5 |
C7—C8—H8B | 109.5 | H27A—C27—H27C | 109.5 |
H8A—C8—H8B | 109.5 | H27B—C27—H27C | 109.5 |
C7—C8—H8C | 109.5 | N9—C28—O4 | 120.7 (2) |
H8A—C8—H8C | 109.5 | N9—C28—C24 | 108.3 (3) |
H8B—C8—H8C | 109.5 | O4—C28—C24 | 130.9 (3) |
N4—C9—H9A | 109.5 | C30—C29—C36 | 122.3 (2) |
N4—C9—H9B | 109.5 | C30—C29—O4 | 115.0 (2) |
H9A—C9—H9B | 109.5 | C36—C29—O4 | 122.6 (2) |
N4—C9—H9C | 109.5 | C29—C30—C31 | 119.6 (3) |
H9A—C9—H9C | 109.5 | C29—C30—H30 | 120.2 |
H9B—C9—H9C | 109.5 | C31—C30—H30 | 120.2 |
N4—C10—O2 | 121.2 (2) | C30—C31—C33 | 118.2 (3) |
N4—C10—C6 | 107.9 (2) | C30—C31—C32 | 121.0 (3) |
O2—C10—C6 | 130.7 (2) | C33—C31—C32 | 120.8 (3) |
C12—C11—C18 | 122.3 (2) | C31—C32—H32A | 109.5 |
C12—C11—O2 | 115.3 (2) | C31—C32—H32B | 109.5 |
C18—C11—O2 | 122.4 (2) | H32A—C32—H32B | 109.5 |
C11—C12—C13 | 119.4 (3) | C31—C32—H32C | 109.5 |
C11—C12—H12 | 120.3 | H32A—C32—H32C | 109.5 |
C13—C12—H12 | 120.3 | H32B—C32—H32C | 109.5 |
C12—C13—C15 | 118.5 (3) | C34—C33—C31 | 122.5 (3) |
C12—C13—C14 | 120.8 (3) | C34—C33—H33 | 118.8 |
C15—C13—C14 | 120.8 (3) | C31—C33—H33 | 118.8 |
C13—C14—H14A | 109.5 | C33—C34—C36 | 118.2 (3) |
C13—C14—H14B | 109.5 | C33—C34—C35 | 121.1 (2) |
H14A—C14—H14B | 109.5 | C36—C34—C35 | 120.7 (3) |
C13—C14—H14C | 109.5 | C34—C35—H35A | 109.5 |
H14A—C14—H14C | 109.5 | C34—C35—H35B | 109.5 |
H14B—C14—H14C | 109.5 | H35A—C35—H35B | 109.5 |
C16—C15—C13 | 122.3 (3) | C34—C35—H35C | 109.5 |
C16—C15—H15 | 118.9 | H35A—C35—H35C | 109.5 |
C13—C15—H15 | 118.9 | H35B—C35—H35C | 109.5 |
C15—C16—C18 | 118.7 (3) | C29—C36—C34 | 119.3 (3) |
C15—C16—C17 | 121.0 (3) | C29—C36—H36 | 120.4 |
C18—C16—C17 | 120.3 (3) | C34—C36—H36 | 120.4 |
C4—O1—N3—C5 | 175.6 (2) | O2—C11—C18—C16 | −178.6 (2) |
C10—N4—N5—C7 | 0.0 (3) | C15—C16—C18—C11 | 0.5 (4) |
C9—N4—N5—C7 | −179.0 (3) | C17—C16—C18—C11 | −179.6 (3) |
C22—O3—N8—C23 | 179.5 (2) | C20—N6—C19—N7 | −1.4 (5) |
C28—N9—N10—C25 | −0.4 (3) | C20—N6—C19—Cl2 | 179.2 (2) |
C27—N9—N10—C25 | 179.5 (3) | C22—N7—C19—N6 | 0.4 (5) |
C2—N1—C1—N2 | −1.0 (4) | C22—N7—C19—Cl2 | 179.9 (2) |
C2—N1—C1—Cl1 | 178.1 (2) | C19—N6—C20—C21 | 1.7 (5) |
C4—N2—C1—N1 | 0.3 (4) | N6—C20—C21—C22 | −1.2 (5) |
C4—N2—C1—Cl1 | −178.8 (2) | C19—N7—C22—O3 | 179.8 (2) |
C1—N1—C2—C3 | 0.2 (4) | C19—N7—C22—C21 | 0.3 (4) |
N1—C2—C3—C4 | 1.0 (4) | N8—O3—C22—N7 | 171.9 (2) |
C1—N2—C4—O1 | −178.9 (2) | N8—O3—C22—C21 | −8.6 (4) |
C1—N2—C4—C3 | 1.3 (4) | C20—C21—C22—N7 | 0.1 (4) |
N3—O1—C4—N2 | −173.0 (2) | C20—C21—C22—O3 | −179.3 (3) |
N3—O1—C4—C3 | 6.9 (4) | O3—N8—C23—C24 | 178.3 (2) |
C2—C3—C4—N2 | −1.9 (4) | N8—C23—C24—C28 | −178.0 (3) |
C2—C3—C4—O1 | 178.3 (2) | N8—C23—C24—C25 | 2.7 (5) |
O1—N3—C5—C6 | −178.2 (2) | N9—N10—C25—C24 | 0.6 (3) |
N3—C5—C6—C10 | 173.8 (3) | N9—N10—C25—C26 | 179.1 (2) |
N3—C5—C6—C7 | −6.7 (5) | C28—C24—C25—N10 | −0.6 (3) |
N4—N5—C7—C6 | −0.1 (3) | C23—C24—C25—N10 | 178.8 (3) |
N4—N5—C7—C8 | −179.6 (3) | C28—C24—C25—C26 | −178.9 (3) |
C10—C6—C7—N5 | 0.1 (3) | C23—C24—C25—C26 | 0.5 (5) |
C5—C6—C7—N5 | −179.5 (3) | N10—N9—C28—O4 | −176.1 (2) |
C10—C6—C7—C8 | 179.6 (3) | C27—N9—C28—O4 | 4.0 (5) |
C5—C6—C7—C8 | 0.0 (5) | N10—N9—C28—C24 | 0.0 (3) |
N5—N4—C10—O2 | 174.5 (2) | C27—N9—C28—C24 | −179.8 (3) |
C9—N4—C10—O2 | −6.5 (4) | C29—O4—C28—N9 | −106.4 (3) |
N5—N4—C10—C6 | 0.1 (3) | C29—O4—C28—C24 | 78.4 (4) |
C9—N4—C10—C6 | 179.1 (3) | C25—C24—C28—N9 | 0.3 (3) |
C11—O2—C10—N4 | 105.7 (3) | C23—C24—C28—N9 | −179.1 (2) |
C11—O2—C10—C6 | −81.3 (3) | C25—C24—C28—O4 | 175.9 (3) |
C7—C6—C10—N4 | −0.1 (3) | C23—C24—C28—O4 | −3.5 (4) |
C5—C6—C10—N4 | 179.5 (2) | C28—O4—C29—C30 | −163.3 (2) |
C7—C6—C10—O2 | −173.8 (3) | C28—O4—C29—C36 | 18.6 (4) |
C5—C6—C10—O2 | 5.8 (4) | C36—C29—C30—C31 | −0.8 (4) |
C10—O2—C11—C12 | 163.6 (2) | O4—C29—C30—C31 | −178.9 (2) |
C10—O2—C11—C18 | −18.2 (3) | C29—C30—C31—C33 | −0.3 (4) |
C18—C11—C12—C13 | −0.2 (4) | C29—C30—C31—C32 | 179.0 (3) |
O2—C11—C12—C13 | 178.0 (2) | C30—C31—C33—C34 | 0.7 (4) |
C11—C12—C13—C15 | 0.9 (4) | C32—C31—C33—C34 | −178.7 (3) |
C11—C12—C13—C14 | −179.7 (3) | C31—C33—C34—C36 | 0.1 (4) |
C12—C13—C15—C16 | −0.9 (4) | C31—C33—C34—C35 | 179.9 (3) |
C14—C13—C15—C16 | 179.7 (3) | C30—C29—C36—C34 | 1.5 (4) |
C13—C15—C16—C18 | 0.2 (4) | O4—C29—C36—C34 | 179.5 (2) |
C13—C15—C16—C17 | −179.7 (3) | C33—C34—C36—C29 | −1.1 (4) |
C12—C11—C18—C16 | −0.5 (4) | C35—C34—C36—C29 | 179.0 (3) |