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
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 |