Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806042887/bt2200sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806042887/bt2200Isup2.hkl |
CCDC reference: 627353
Key indicators
- Single-crystal X-ray study
- T = 273 K
- Mean (C-C) = 0.010 Å
- R factor = 0.094
- wR factor = 0.329
- Data-to-parameter ratio = 12.7
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT029_ALERT_3_B _diffrn_measured_fraction_theta_full Low ....... 0.94
Alert level C REFLT03_ALERT_3_C Reflection count < 95% complete From the CIF: _diffrn_reflns_theta_max 25.00 From the CIF: _diffrn_reflns_theta_full 25.00 From the CIF: _reflns_number_total 5569 TEST2: Reflns within _diffrn_reflns_theta_max Count of symmetry unique reflns 5912 Completeness (_total/calc) 94.20% RFACR01_ALERT_3_C The value of the weighted R factor is > 0.25 Weighted R factor given 0.329 PLAT022_ALERT_3_C Ratio Unique / Expected Reflections too Low .... 0.94 PLAT084_ALERT_2_C High R2 Value .................................. 0.33 PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 10
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 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 5 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
Data collection: SMART (Bruker,1998); cell refinement: SMART; data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1998); software used to prepare material for publication: SHELXTL.
C18H15Cl2N3O | F(000) = 1488 |
Mr = 360.23 | Dx = 1.421 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 7.591 (5) Å | Cell parameters from 5299 reflections |
b = 25.808 (18) Å | θ = 2.4–25.1° |
c = 17.216 (12) Å | µ = 0.40 mm−1 |
β = 92.823 (8)° | T = 273 K |
V = 3369 (4) Å3 | Block, yellow |
Z = 8 | 0.37 × 0.24 × 0.20 mm |
Bruker SMART CCD area-detector diffractometer | 5569 independent reflections |
Radiation source: fine-focus sealed tube | 3386 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.042 |
φ and ω scans | θmax = 25.0°, θmin = 2.0° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −8→8 |
Tmin = 0.868, Tmax = 0.925 | k = −30→30 |
19762 measured reflections | l = −20→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)] = 0.094 | H-atom parameters constrained |
wR(F2) = 0.329 | w = 1/[σ2(Fo2) + (0.1683P)2 + 4.5478P] where P = (Fo2 + 2Fc2)/3 |
S = 1.16 | (Δ/σ)max < 0.001 |
5569 reflections | Δρmax = 0.48 e Å−3 |
438 parameters | Δρmin = −1.24 e Å−3 |
0 restraints | Extinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.015 (3) |
Experimental. Spectroscopic analysis: 1H NMR (300 MHz, CDCl3, δ, p.p.m.): 9.98 (s, 1H), 7.52–7.17 (m, 8H), 3.21 (s, 3H), 2.49 (s, 3H); IR (KBr, ν, cm-1): 3437, 3044, 2940, 1651, 1580, 1491, 1415, 1307, 1187, 1132, 946, 775, 694. |
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 | ||
C1 | 0.6930 (11) | 0.6266 (3) | 0.1237 (5) | 0.083 (2) | |
H1 | 0.7129 | 0.6616 | 0.1151 | 0.100* | |
C2 | 0.6268 (11) | 0.6109 (3) | 0.1929 (4) | 0.077 (2) | |
H2 | 0.6047 | 0.6351 | 0.2313 | 0.092* | |
C3 | 0.5939 (10) | 0.5595 (3) | 0.2047 (4) | 0.0670 (17) | |
C4 | 0.6275 (9) | 0.5212 (2) | 0.1492 (3) | 0.0594 (15) | |
C5 | 0.6988 (10) | 0.5393 (3) | 0.0806 (4) | 0.0678 (18) | |
C6 | 0.7298 (11) | 0.5912 (3) | 0.0671 (4) | 0.077 (2) | |
H6 | 0.7748 | 0.6020 | 0.0205 | 0.093* | |
C7 | 0.5818 (9) | 0.4659 (2) | 0.1558 (4) | 0.0613 (16) | |
H7 | 0.5431 | 0.4482 | 0.1111 | 0.074* | |
C8 | 0.5416 (9) | 0.3894 (2) | 0.2220 (3) | 0.0590 (16) | |
C9 | 0.5574 (9) | 0.3595 (2) | 0.2884 (3) | 0.0561 (15) | |
C10 | 0.6120 (11) | 0.3763 (3) | 0.3689 (3) | 0.0708 (19) | |
H10A | 0.5135 | 0.3735 | 0.4015 | 0.106* | |
H10B | 0.6513 | 0.4117 | 0.3680 | 0.106* | |
H10C | 0.7063 | 0.3546 | 0.3890 | 0.106* | |
C11 | 0.4462 (10) | 0.2730 (3) | 0.3267 (4) | 0.0704 (18) | |
H11A | 0.5165 | 0.2744 | 0.3746 | 0.106* | |
H11B | 0.4521 | 0.2388 | 0.3051 | 0.106* | |
H11C | 0.3260 | 0.2812 | 0.3365 | 0.106* | |
C12 | 0.4485 (9) | 0.2605 (2) | 0.1528 (3) | 0.0581 (15) | |
C13 | 0.3126 (10) | 0.2498 (3) | 0.0986 (4) | 0.0700 (18) | |
H13 | 0.2219 | 0.2735 | 0.0888 | 0.084* | |
C14 | 0.3151 (13) | 0.2032 (3) | 0.0594 (4) | 0.083 (2) | |
H14 | 0.2258 | 0.1959 | 0.0221 | 0.100* | |
C15 | 0.4451 (13) | 0.1675 (3) | 0.0739 (4) | 0.086 (3) | |
H15 | 0.4419 | 0.1360 | 0.0478 | 0.103* | |
C16 | 0.5815 (13) | 0.1784 (3) | 0.1275 (4) | 0.083 (2) | |
H16 | 0.6713 | 0.1544 | 0.1371 | 0.099* | |
C17 | 0.5841 (10) | 0.2251 (2) | 0.1669 (4) | 0.0672 (18) | |
H17 | 0.6762 | 0.2327 | 0.2026 | 0.081* | |
C18 | 0.4735 (10) | 0.3566 (2) | 0.1601 (3) | 0.0618 (16) | |
C1' | 0.7931 (11) | 0.1101 (3) | 0.3729 (4) | 0.078 (2) | |
H1' | 0.7545 | 0.0761 | 0.3783 | 0.093* | |
C2' | 0.8741 (10) | 0.1248 (3) | 0.3069 (4) | 0.0716 (19) | |
H2' | 0.8900 | 0.1007 | 0.2676 | 0.086* | |
C3' | 0.9326 (10) | 0.1752 (2) | 0.2984 (4) | 0.0636 (17) | |
C4' | 0.9103 (9) | 0.2127 (2) | 0.3558 (3) | 0.0591 (15) | |
C5' | 0.8273 (10) | 0.1961 (3) | 0.4224 (4) | 0.0674 (18) | |
C6' | 0.7687 (11) | 0.1456 (3) | 0.4313 (4) | 0.078 (2) | |
H6' | 0.7136 | 0.1358 | 0.4761 | 0.094* | |
C7' | 0.9718 (9) | 0.2667 (2) | 0.3509 (3) | 0.0595 (15) | |
H7' | 1.0185 | 0.2828 | 0.3957 | 0.071* | |
C8' | 1.0200 (9) | 0.3438 (2) | 0.2855 (3) | 0.0557 (15) | |
C9' | 1.0025 (9) | 0.3743 (2) | 0.2201 (3) | 0.0570 (15) | |
C10' | 0.9456 (10) | 0.3584 (3) | 0.1398 (3) | 0.0690 (18) | |
H10D | 0.8516 | 0.3806 | 0.1206 | 0.104* | |
H10E | 0.9050 | 0.3232 | 0.1402 | 0.104* | |
H10F | 1.0433 | 0.3613 | 0.1068 | 0.104* | |
C11' | 1.1085 (10) | 0.4618 (3) | 0.1831 (4) | 0.073 (2) | |
H11D | 1.2256 | 0.4529 | 0.1691 | 0.110* | |
H11E | 1.1098 | 0.4955 | 0.2069 | 0.110* | |
H11F | 1.0311 | 0.4623 | 0.1373 | 0.110* | |
C12' | 1.1033 (9) | 0.4725 (2) | 0.3582 (3) | 0.0608 (16) | |
C13' | 0.9642 (11) | 0.5060 (3) | 0.3444 (4) | 0.0724 (19) | |
H13' | 0.8749 | 0.4984 | 0.3072 | 0.087* | |
C14' | 0.9603 (13) | 0.5513 (3) | 0.3872 (5) | 0.088 (2) | |
H14' | 0.8690 | 0.5748 | 0.3775 | 0.106* | |
C15' | 1.0883 (14) | 0.5623 (3) | 0.4435 (5) | 0.090 (3) | |
H15' | 1.0830 | 0.5927 | 0.4723 | 0.108* | |
C16' | 1.2242 (13) | 0.5281 (3) | 0.4573 (4) | 0.090 (2) | |
H16' | 1.3106 | 0.5353 | 0.4960 | 0.108* | |
C17' | 1.2347 (11) | 0.4829 (3) | 0.4144 (4) | 0.0739 (19) | |
H17' | 1.3282 | 0.4600 | 0.4232 | 0.089* | |
C18' | 1.0880 (9) | 0.3758 (2) | 0.3484 (3) | 0.0589 (16) | |
Cl1 | 0.4916 (3) | 0.54329 (7) | 0.28996 (10) | 0.0794 (6) | |
Cl2 | 0.7512 (3) | 0.49492 (8) | 0.00907 (10) | 0.0843 (7) | |
Cl1' | 0.7895 (3) | 0.24020 (8) | 0.49602 (10) | 0.0891 (7) | |
Cl2' | 1.0449 (3) | 0.18909 (7) | 0.21537 (10) | 0.0752 (6) | |
N1 | 0.5930 (8) | 0.44116 (19) | 0.2199 (3) | 0.0593 (13) | |
N2 | 0.5130 (8) | 0.31018 (18) | 0.2721 (3) | 0.0592 (14) | |
N3 | 0.4479 (8) | 0.30849 (18) | 0.1943 (3) | 0.0613 (14) | |
N1' | 0.9633 (8) | 0.29229 (19) | 0.2873 (3) | 0.0600 (13) | |
N2' | 1.0462 (8) | 0.42362 (18) | 0.2378 (3) | 0.0583 (13) | |
N3' | 1.1135 (8) | 0.42482 (18) | 0.3152 (3) | 0.0591 (13) | |
O1 | 0.4440 (8) | 0.36525 (17) | 0.0898 (2) | 0.0798 (15) | |
O1' | 1.1236 (7) | 0.36631 (16) | 0.4178 (2) | 0.0752 (14) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.103 (6) | 0.054 (4) | 0.092 (6) | −0.014 (4) | −0.007 (5) | 0.009 (4) |
C2 | 0.100 (6) | 0.051 (4) | 0.079 (5) | −0.004 (4) | 0.004 (4) | −0.008 (3) |
C3 | 0.095 (5) | 0.055 (4) | 0.051 (4) | −0.001 (3) | 0.001 (3) | 0.004 (3) |
C4 | 0.083 (4) | 0.050 (3) | 0.044 (3) | 0.004 (3) | −0.002 (3) | 0.003 (3) |
C5 | 0.090 (5) | 0.061 (4) | 0.052 (4) | −0.003 (3) | −0.007 (3) | 0.005 (3) |
C6 | 0.100 (5) | 0.073 (5) | 0.060 (4) | −0.010 (4) | −0.001 (4) | 0.019 (4) |
C7 | 0.083 (4) | 0.052 (4) | 0.048 (3) | 0.002 (3) | 0.001 (3) | −0.002 (3) |
C8 | 0.091 (4) | 0.045 (3) | 0.042 (3) | 0.003 (3) | 0.001 (3) | 0.000 (3) |
C9 | 0.078 (4) | 0.048 (3) | 0.042 (3) | 0.007 (3) | 0.007 (3) | −0.002 (3) |
C10 | 0.105 (5) | 0.064 (4) | 0.043 (3) | 0.001 (4) | −0.002 (3) | −0.006 (3) |
C11 | 0.094 (5) | 0.069 (4) | 0.049 (4) | −0.002 (4) | 0.004 (3) | 0.011 (3) |
C12 | 0.088 (4) | 0.044 (3) | 0.042 (3) | 0.002 (3) | 0.004 (3) | 0.001 (3) |
C13 | 0.088 (5) | 0.070 (4) | 0.051 (4) | −0.001 (4) | −0.007 (3) | −0.003 (3) |
C14 | 0.120 (7) | 0.081 (5) | 0.048 (4) | −0.020 (5) | −0.001 (4) | −0.014 (4) |
C15 | 0.150 (8) | 0.054 (4) | 0.057 (4) | −0.007 (5) | 0.024 (5) | −0.010 (3) |
C16 | 0.135 (7) | 0.057 (4) | 0.056 (4) | 0.012 (4) | 0.012 (5) | −0.001 (3) |
C17 | 0.101 (5) | 0.052 (4) | 0.048 (3) | 0.005 (3) | 0.000 (3) | 0.002 (3) |
C18 | 0.096 (5) | 0.047 (3) | 0.042 (3) | 0.008 (3) | 0.001 (3) | 0.003 (3) |
C1' | 0.099 (6) | 0.061 (4) | 0.072 (5) | −0.017 (4) | −0.009 (4) | 0.015 (4) |
C2' | 0.092 (5) | 0.051 (4) | 0.071 (4) | −0.003 (3) | −0.002 (4) | 0.000 (3) |
C3' | 0.087 (4) | 0.052 (4) | 0.052 (4) | 0.003 (3) | 0.003 (3) | 0.005 (3) |
C4' | 0.081 (4) | 0.051 (3) | 0.046 (3) | 0.003 (3) | −0.001 (3) | 0.005 (3) |
C5' | 0.090 (5) | 0.062 (4) | 0.048 (4) | 0.006 (4) | −0.007 (3) | 0.010 (3) |
C6' | 0.096 (5) | 0.079 (5) | 0.059 (4) | −0.009 (4) | −0.005 (4) | 0.025 (4) |
C7' | 0.079 (4) | 0.055 (4) | 0.045 (3) | 0.003 (3) | 0.005 (3) | 0.001 (3) |
C8' | 0.082 (4) | 0.044 (3) | 0.041 (3) | 0.000 (3) | 0.004 (3) | 0.002 (3) |
C9' | 0.084 (4) | 0.049 (3) | 0.039 (3) | 0.004 (3) | 0.008 (3) | 0.000 (3) |
C10' | 0.102 (5) | 0.062 (4) | 0.043 (3) | 0.000 (4) | −0.001 (3) | −0.001 (3) |
C11' | 0.109 (6) | 0.064 (4) | 0.047 (3) | −0.010 (4) | 0.007 (4) | 0.011 (3) |
C12' | 0.092 (5) | 0.046 (3) | 0.045 (3) | 0.000 (3) | 0.013 (3) | −0.002 (3) |
C13' | 0.101 (5) | 0.053 (4) | 0.063 (4) | 0.009 (4) | 0.003 (4) | 0.000 (3) |
C14' | 0.123 (7) | 0.058 (4) | 0.084 (5) | 0.011 (4) | 0.020 (5) | −0.004 (4) |
C15' | 0.131 (7) | 0.057 (4) | 0.085 (6) | −0.009 (5) | 0.034 (5) | −0.018 (4) |
C16' | 0.123 (7) | 0.085 (6) | 0.063 (5) | −0.020 (5) | 0.001 (5) | −0.020 (4) |
C17' | 0.101 (5) | 0.066 (4) | 0.054 (4) | −0.006 (4) | −0.002 (4) | −0.007 (3) |
C18' | 0.088 (4) | 0.047 (3) | 0.042 (3) | 0.006 (3) | 0.004 (3) | 0.005 (3) |
Cl1 | 0.1132 (15) | 0.0627 (11) | 0.0638 (11) | 0.0023 (10) | 0.0198 (10) | −0.0072 (8) |
Cl2 | 0.1141 (17) | 0.0882 (14) | 0.0517 (10) | −0.0005 (11) | 0.0157 (10) | 0.0009 (9) |
Cl1' | 0.1342 (18) | 0.0842 (13) | 0.0503 (10) | 0.0090 (12) | 0.0186 (11) | 0.0044 (8) |
Cl2' | 0.1086 (14) | 0.0595 (10) | 0.0589 (10) | 0.0028 (9) | 0.0190 (9) | −0.0015 (8) |
N1 | 0.085 (4) | 0.044 (3) | 0.048 (3) | 0.000 (3) | 0.003 (3) | 0.001 (2) |
N2 | 0.097 (4) | 0.043 (3) | 0.038 (3) | 0.001 (3) | 0.001 (3) | 0.001 (2) |
N3 | 0.098 (4) | 0.047 (3) | 0.039 (3) | 0.002 (3) | −0.004 (3) | 0.003 (2) |
N1' | 0.090 (4) | 0.045 (3) | 0.045 (3) | 0.005 (3) | 0.001 (3) | 0.002 (2) |
N2' | 0.093 (4) | 0.045 (3) | 0.037 (2) | 0.004 (3) | 0.005 (2) | 0.004 (2) |
N3' | 0.090 (4) | 0.045 (3) | 0.041 (3) | 0.000 (3) | −0.006 (3) | 0.002 (2) |
O1 | 0.132 (4) | 0.058 (3) | 0.047 (3) | 0.001 (3) | −0.020 (3) | 0.006 (2) |
O1' | 0.124 (4) | 0.055 (3) | 0.045 (2) | 0.003 (3) | −0.014 (2) | 0.005 (2) |
C1—C6 | 1.374 (11) | C1'—C6' | 1.379 (11) |
C1—C2 | 1.378 (10) | C1'—H1' | 0.9300 |
C1—H1 | 0.9300 | C2'—C3' | 1.384 (9) |
C2—C3 | 1.367 (9) | C2'—H2' | 0.9300 |
C2—H2 | 0.9300 | C3'—C4' | 1.399 (9) |
C3—C4 | 1.407 (9) | C3'—Cl2' | 1.738 (7) |
C3—Cl1 | 1.744 (7) | C4'—C5' | 1.403 (9) |
C4—C5 | 1.404 (9) | C4'—C7' | 1.474 (9) |
C4—C7 | 1.475 (9) | C5'—C6' | 1.388 (10) |
C5—C6 | 1.382 (10) | C5'—Cl1' | 1.738 (7) |
C5—Cl2 | 1.743 (7) | C6'—H6' | 0.9300 |
C6—H6 | 0.9300 | C7'—N1' | 1.277 (7) |
C7—N1 | 1.274 (7) | C7'—H7' | 0.9300 |
C7—H7 | 0.9300 | C8'—C9' | 1.375 (8) |
C8—C9 | 1.378 (8) | C8'—N1' | 1.398 (8) |
C8—N1 | 1.393 (8) | C8'—C18' | 1.437 (8) |
C8—C18 | 1.436 (8) | C9'—N2' | 1.347 (8) |
C9—N2 | 1.342 (8) | C9'—C10' | 1.486 (8) |
C9—C10 | 1.492 (8) | C10'—H10D | 0.9600 |
C10—H10A | 0.9600 | C10'—H10E | 0.9600 |
C10—H10B | 0.9600 | C10'—H10F | 0.9600 |
C10—H10C | 0.9600 | C11'—N2' | 1.459 (8) |
C11—N2 | 1.453 (8) | C11'—H11D | 0.9600 |
C11—H11A | 0.9600 | C11'—H11E | 0.9600 |
C11—H11B | 0.9600 | C11'—H11F | 0.9600 |
C11—H11C | 0.9600 | C12'—C13' | 1.377 (9) |
C12—C13 | 1.385 (9) | C12'—C17' | 1.381 (9) |
C12—C17 | 1.388 (9) | C12'—N3' | 1.439 (7) |
C12—N3 | 1.430 (7) | C13'—C14' | 1.384 (10) |
C13—C14 | 1.379 (10) | C13'—H13' | 0.9300 |
C13—H13 | 0.9300 | C14'—C15' | 1.367 (12) |
C14—C15 | 1.363 (11) | C14'—H14' | 0.9300 |
C14—H14 | 0.9300 | C15'—C16' | 1.370 (12) |
C15—C16 | 1.381 (12) | C15'—H15' | 0.9300 |
C15—H15 | 0.9300 | C16'—C17' | 1.386 (10) |
C16—C17 | 1.381 (9) | C16'—H16' | 0.9300 |
C16—H16 | 0.9300 | C17'—H17' | 0.9300 |
C17—H17 | 0.9300 | C18'—O1' | 1.236 (7) |
C18—O1 | 1.240 (7) | C18'—N3' | 1.406 (7) |
C18—N3 | 1.392 (8) | N2—N3 | 1.406 (6) |
C1'—C2' | 1.372 (10) | N2'—N3' | 1.404 (7) |
C6—C1—C2 | 121.0 (7) | C2'—C3'—Cl2' | 117.0 (5) |
C6—C1—H1 | 119.5 | C4'—C3'—Cl2' | 121.2 (5) |
C2—C1—H1 | 119.5 | C3'—C4'—C5' | 116.0 (6) |
C3—C2—C1 | 119.4 (7) | C3'—C4'—C7' | 124.4 (6) |
C3—C2—H2 | 120.3 | C5'—C4'—C7' | 119.5 (6) |
C1—C2—H2 | 120.3 | C6'—C5'—C4' | 122.5 (6) |
C2—C3—C4 | 122.7 (6) | C6'—C5'—Cl1' | 118.0 (6) |
C2—C3—Cl1 | 116.7 (5) | C4'—C5'—Cl1' | 119.5 (5) |
C4—C3—Cl1 | 120.4 (5) | C1'—C6'—C5' | 119.2 (7) |
C5—C4—C3 | 115.3 (6) | C1'—C6'—H6' | 120.4 |
C5—C4—C7 | 119.3 (6) | C5'—C6'—H6' | 120.4 |
C3—C4—C7 | 125.2 (6) | N1'—C7'—C4' | 122.3 (6) |
C6—C5—C4 | 122.8 (6) | N1'—C7'—H7' | 118.9 |
C6—C5—Cl2 | 118.1 (5) | C4'—C7'—H7' | 118.9 |
C4—C5—Cl2 | 119.1 (5) | C9'—C8'—N1' | 123.0 (5) |
C1—C6—C5 | 118.8 (7) | C9'—C8'—C18' | 107.7 (5) |
C1—C6—H6 | 120.6 | N1'—C8'—C18' | 129.0 (5) |
C5—C6—H6 | 120.6 | N2'—C9'—C8' | 110.1 (5) |
N1—C7—C4 | 123.0 (6) | N2'—C9'—C10' | 121.9 (5) |
N1—C7—H7 | 118.5 | C8'—C9'—C10' | 128.1 (6) |
C4—C7—H7 | 118.5 | C9'—C10'—H10D | 109.5 |
C9—C8—N1 | 123.0 (5) | C9'—C10'—H10E | 109.5 |
C9—C8—C18 | 107.4 (5) | H10D—C10'—H10E | 109.5 |
N1—C8—C18 | 129.5 (5) | C9'—C10'—H10F | 109.5 |
N2—C9—C8 | 110.3 (5) | H10D—C10'—H10F | 109.5 |
N2—C9—C10 | 121.7 (5) | H10E—C10'—H10F | 109.5 |
C8—C9—C10 | 128.0 (6) | N2'—C11'—H11D | 109.5 |
C9—C10—H10A | 109.5 | N2'—C11'—H11E | 109.5 |
C9—C10—H10B | 109.5 | H11D—C11'—H11E | 109.5 |
H10A—C10—H10B | 109.5 | N2'—C11'—H11F | 109.5 |
C9—C10—H10C | 109.5 | H11D—C11'—H11F | 109.5 |
H10A—C10—H10C | 109.5 | H11E—C11'—H11F | 109.5 |
H10B—C10—H10C | 109.5 | C13'—C12'—C17' | 121.3 (6) |
N2—C11—H11A | 109.5 | C13'—C12'—N3' | 120.6 (6) |
N2—C11—H11B | 109.5 | C17'—C12'—N3' | 118.1 (6) |
H11A—C11—H11B | 109.5 | C12'—C13'—C14' | 118.4 (8) |
N2—C11—H11C | 109.5 | C12'—C13'—H13' | 120.8 |
H11A—C11—H11C | 109.5 | C14'—C13'—H13' | 120.8 |
H11B—C11—H11C | 109.5 | C15'—C14'—C13' | 121.3 (8) |
C13—C12—C17 | 120.5 (6) | C15'—C14'—H14' | 119.4 |
C13—C12—N3 | 119.2 (6) | C13'—C14'—H14' | 119.4 |
C17—C12—N3 | 120.3 (6) | C14'—C15'—C16' | 119.5 (7) |
C14—C13—C12 | 118.4 (7) | C14'—C15'—H15' | 120.2 |
C14—C13—H13 | 120.8 | C16'—C15'—H15' | 120.2 |
C12—C13—H13 | 120.8 | C15'—C16'—C17' | 120.8 (8) |
C15—C14—C13 | 121.7 (8) | C15'—C16'—H16' | 119.6 |
C15—C14—H14 | 119.1 | C17'—C16'—H16' | 119.6 |
C13—C14—H14 | 119.1 | C12'—C17'—C16' | 118.6 (8) |
C14—C15—C16 | 119.8 (7) | C12'—C17'—H17' | 120.7 |
C14—C15—H15 | 120.1 | C16'—C17'—H17' | 120.7 |
C16—C15—H15 | 120.1 | O1'—C18'—N3' | 122.9 (6) |
C17—C16—C15 | 119.8 (8) | O1'—C18'—C8' | 131.9 (6) |
C17—C16—H16 | 120.1 | N3'—C18'—C8' | 105.2 (5) |
C15—C16—H16 | 120.1 | C7—N1—C8 | 119.7 (5) |
C16—C17—C12 | 119.7 (7) | C9—N2—N3 | 107.5 (4) |
C16—C17—H17 | 120.1 | C9—N2—C11 | 125.7 (5) |
C12—C17—H17 | 120.1 | N3—N2—C11 | 118.6 (5) |
O1—C18—N3 | 123.3 (6) | C18—N3—N2 | 109.0 (5) |
O1—C18—C8 | 131.3 (6) | C18—N3—C12 | 124.0 (5) |
N3—C18—C8 | 105.3 (5) | N2—N3—C12 | 119.5 (5) |
C2'—C1'—C6' | 120.1 (7) | C7'—N1'—C8' | 120.4 (5) |
C2'—C1'—H1' | 120.0 | C9'—N2'—N3' | 108.0 (4) |
C6'—C1'—H1' | 120.0 | C9'—N2'—C11' | 125.3 (5) |
C1'—C2'—C3' | 120.5 (7) | N3'—N2'—C11' | 118.9 (5) |
C1'—C2'—H2' | 119.8 | N2'—N3'—C18' | 108.4 (5) |
C3'—C2'—H2' | 119.8 | N2'—N3'—C12' | 118.7 (5) |
C2'—C3'—C4' | 121.7 (6) | C18'—N3'—C12' | 123.2 (5) |
D—H···A | D—H | H···A | D···A | D—H···A |
C7—H7···O1 | 0.93 | 2.29 | 3.002 (8) | 133 |
C7′—H7′···O1′ | 0.93 | 2.32 | 3.021 (8) | 132 |