Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806051452/hb2221sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806051452/hb2221Isup2.hkl |
CCDC reference: 633864
Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; 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.
C25H18Cl2N2·0.5CHCl3 | F(000) = 980 |
Mr = 477.00 | Dx = 1.390 Mg m−3 |
Monoclinic, P21/c | Melting point = 442–443 K |
Hall symbol: -P 2ybc | Mo Kα radiation, λ = 0.71073 Å |
a = 14.494 (3) Å | Cell parameters from 2253 reflections |
b = 10.616 (2) Å | θ = 2.4–21.0° |
c = 15.573 (3) Å | µ = 0.48 mm−1 |
β = 107.910 (4)° | T = 294 K |
V = 2280.1 (8) Å3 | Block, colourless |
Z = 2 | 0.28 × 0.24 × 0.20 mm |
Bruker SMART CCD diffractometer | 4032 independent reflections |
Radiation source: fine-focus sealed tube | 2298 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.049 |
ω scans | θmax = 25.0°, θmin = 1.5° |
Absorption correction: multi-scan (SADABS; Bruker, 1998) | h = −17→15 |
Tmin = 0.878, Tmax = 0.911 | k = −9→12 |
11344 measured reflections | l = −17→18 |
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)] = 0.051 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.138 | H-atom parameters constrained |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0572P)2 + 0.7045P] where P = (Fo2 + 2Fc2)/3 |
4032 reflections | (Δ/σ)max = 0.005 |
334 parameters | Δρmax = 0.37 e Å−3 |
110 restraints | Δρmin = −0.34 e Å−3 |
Experimental. 1H NMR (CDCl3): δ 8.18 (d, 1H), 7.85–7.78 (m, 4H), 7.48 (dd, 2H), 7.46 (dd, 1H), 7.25 (d, 1H), 7.23–7.13 (m, 3H), 7.04 (dd, 2H), 6.80 (dd, 1H), 6.09 (dd, 1H), 3.87 (dd, 1H), 3.45 (dd, 1H). |
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) | |
Cl1 | 0.83034 (7) | 0.78548 (9) | 0.00551 (6) | 0.0708 (3) | |
Cl2 | 0.78912 (8) | 0.49430 (9) | 0.28148 (6) | 0.0789 (3) | |
N1 | 0.63598 (19) | 0.3974 (2) | 0.09493 (16) | 0.0477 (7) | |
N2 | 0.71732 (19) | 0.4434 (2) | 0.07828 (17) | 0.0494 (7) | |
C1 | 0.8679 (2) | 0.7299 (3) | 0.1162 (2) | 0.0495 (8) | |
C2 | 0.9518 (3) | 0.7822 (4) | 0.1744 (3) | 0.0676 (11) | |
H2 | 0.9853 | 0.8442 | 0.1540 | 0.081* | |
C3 | 0.9852 (3) | 0.7414 (4) | 0.2626 (3) | 0.0766 (12) | |
H3 | 1.0417 | 0.7753 | 0.3017 | 0.092* | |
C4 | 0.9352 (3) | 0.6514 (4) | 0.2923 (3) | 0.0695 (11) | |
H4 | 0.9578 | 0.6239 | 0.3518 | 0.083* | |
C5 | 0.8510 (2) | 0.6010 (3) | 0.2344 (2) | 0.0542 (9) | |
C6 | 0.8146 (2) | 0.6372 (3) | 0.1438 (2) | 0.0433 (8) | |
C7 | 0.7212 (2) | 0.5829 (3) | 0.0790 (2) | 0.0442 (8) | |
H7 | 0.7144 | 0.6127 | 0.0178 | 0.053* | |
C8 | 0.6288 (2) | 0.6174 (3) | 0.1029 (2) | 0.0476 (8) | |
H8A | 0.6443 | 0.6637 | 0.1592 | 0.057* | |
H8B | 0.5848 | 0.6672 | 0.0555 | 0.057* | |
C9 | 0.5859 (2) | 0.4904 (3) | 0.1112 (2) | 0.0447 (8) | |
C10 | 0.4983 (2) | 0.4709 (3) | 0.13736 (19) | 0.0430 (8) | |
C11 | 0.4476 (2) | 0.5712 (3) | 0.15551 (19) | 0.0470 (8) | |
H11 | 0.4694 | 0.6523 | 0.1500 | 0.056* | |
C12 | 0.3636 (2) | 0.5561 (3) | 0.18226 (19) | 0.0451 (8) | |
C13 | 0.3125 (2) | 0.6591 (3) | 0.2032 (2) | 0.0563 (9) | |
H13 | 0.3342 | 0.7407 | 0.1993 | 0.068* | |
C14 | 0.2322 (3) | 0.6407 (4) | 0.2291 (2) | 0.0666 (10) | |
H14 | 0.2003 | 0.7095 | 0.2438 | 0.080* | |
C15 | 0.1969 (3) | 0.5185 (4) | 0.2336 (3) | 0.0719 (11) | |
H15 | 0.1408 | 0.5069 | 0.2499 | 0.086* | |
C16 | 0.2445 (3) | 0.4170 (4) | 0.2144 (2) | 0.0626 (10) | |
H16 | 0.2207 | 0.3365 | 0.2181 | 0.075* | |
C17 | 0.3294 (2) | 0.4315 (3) | 0.1888 (2) | 0.0476 (8) | |
C18 | 0.3829 (2) | 0.3292 (3) | 0.1701 (2) | 0.0531 (9) | |
H18 | 0.3613 | 0.2475 | 0.1740 | 0.064* | |
C19 | 0.4649 (2) | 0.3468 (3) | 0.1466 (2) | 0.0498 (8) | |
H19 | 0.4994 | 0.2775 | 0.1364 | 0.060* | |
C20 | 0.7763 (2) | 0.3633 (3) | 0.04780 (18) | 0.0418 (8) | |
C21 | 0.8525 (2) | 0.4103 (3) | 0.0205 (2) | 0.0528 (9) | |
H21 | 0.8636 | 0.4966 | 0.0216 | 0.063* | |
C22 | 0.9120 (3) | 0.3294 (3) | −0.0083 (2) | 0.0615 (10) | |
H22 | 0.9626 | 0.3617 | −0.0266 | 0.074* | |
C23 | 0.8965 (3) | 0.2009 (4) | −0.0100 (2) | 0.0650 (10) | |
H23 | 0.9366 | 0.1465 | −0.0290 | 0.078* | |
C24 | 0.8220 (3) | 0.1548 (3) | 0.0165 (2) | 0.0662 (10) | |
H24 | 0.8111 | 0.0684 | 0.0147 | 0.079* | |
C25 | 0.7620 (3) | 0.2340 (3) | 0.0461 (2) | 0.0547 (9) | |
H25 | 0.7121 | 0.2004 | 0.0648 | 0.066* | |
Cl3' | 0.3908 (4) | 0.4413 (5) | 0.4506 (5) | 0.105 (2) | 0.30 |
Cl4' | 0.5573 (6) | 0.5354 (8) | 0.5856 (5) | 0.150 (3) | 0.30 |
Cl5' | 0.5598 (5) | 0.4870 (7) | 0.3983 (4) | 0.143 (3) | 0.30 |
C26' | 0.5230 (7) | 0.4357 (12) | 0.4896 (6) | 0.094 (4) | 0.30 |
H26B | 0.5382 | 0.3502 | 0.5087 | 0.112* | 0.30 |
Cl3 | 0.3965 (6) | 0.4476 (9) | 0.5046 (6) | 0.126 (2) | 0.20 |
Cl4 | 0.5982 (7) | 0.5234 (10) | 0.5732 (6) | 0.092 (3) | 0.20 |
Cl5 | 0.5238 (8) | 0.4450 (10) | 0.3966 (6) | 0.128 (3) | 0.20 |
C26 | 0.4898 (8) | 0.5339 (15) | 0.4789 (8) | 0.097 (7) | 0.20 |
H26A | 0.4634 | 0.6165 | 0.4620 | 0.117* | 0.20 |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0780 (7) | 0.0635 (6) | 0.0747 (6) | −0.0146 (5) | 0.0290 (5) | 0.0068 (5) |
Cl2 | 0.0957 (8) | 0.0770 (7) | 0.0581 (5) | −0.0070 (6) | 0.0148 (5) | 0.0143 (5) |
N1 | 0.0509 (17) | 0.0424 (15) | 0.0528 (15) | −0.0044 (13) | 0.0202 (13) | −0.0049 (13) |
N2 | 0.0504 (16) | 0.0398 (15) | 0.0650 (17) | −0.0052 (13) | 0.0279 (14) | −0.0076 (13) |
C1 | 0.046 (2) | 0.048 (2) | 0.059 (2) | −0.0025 (16) | 0.0217 (16) | −0.0108 (16) |
C2 | 0.052 (2) | 0.072 (3) | 0.085 (3) | −0.0190 (19) | 0.030 (2) | −0.030 (2) |
C3 | 0.044 (2) | 0.109 (3) | 0.071 (3) | −0.008 (2) | 0.009 (2) | −0.036 (2) |
C4 | 0.054 (2) | 0.089 (3) | 0.058 (2) | 0.007 (2) | 0.006 (2) | −0.017 (2) |
C5 | 0.051 (2) | 0.051 (2) | 0.060 (2) | 0.0072 (17) | 0.0163 (18) | −0.0072 (17) |
C6 | 0.0411 (18) | 0.0401 (18) | 0.0475 (18) | 0.0039 (14) | 0.0120 (15) | −0.0060 (15) |
C7 | 0.0436 (19) | 0.0424 (18) | 0.0456 (17) | −0.0022 (15) | 0.0121 (15) | −0.0022 (15) |
C8 | 0.0443 (19) | 0.0431 (19) | 0.0552 (19) | 0.0023 (15) | 0.0150 (16) | −0.0022 (15) |
C9 | 0.0434 (18) | 0.0442 (19) | 0.0438 (17) | −0.0009 (16) | 0.0092 (14) | −0.0019 (15) |
C10 | 0.0392 (18) | 0.0444 (19) | 0.0440 (17) | −0.0022 (15) | 0.0107 (15) | −0.0007 (14) |
C11 | 0.048 (2) | 0.0418 (19) | 0.0508 (19) | −0.0061 (15) | 0.0146 (16) | 0.0008 (15) |
C12 | 0.0416 (19) | 0.050 (2) | 0.0415 (17) | −0.0029 (16) | 0.0100 (15) | 0.0014 (15) |
C13 | 0.053 (2) | 0.053 (2) | 0.065 (2) | 0.0040 (17) | 0.0216 (18) | 0.0010 (17) |
C14 | 0.061 (2) | 0.071 (3) | 0.075 (2) | 0.012 (2) | 0.031 (2) | 0.001 (2) |
C15 | 0.057 (2) | 0.088 (3) | 0.079 (3) | 0.003 (2) | 0.034 (2) | 0.008 (2) |
C16 | 0.058 (2) | 0.067 (2) | 0.065 (2) | −0.006 (2) | 0.0222 (19) | 0.0155 (19) |
C17 | 0.045 (2) | 0.055 (2) | 0.0412 (17) | −0.0041 (17) | 0.0101 (15) | 0.0053 (16) |
C18 | 0.057 (2) | 0.043 (2) | 0.057 (2) | −0.0098 (17) | 0.0152 (17) | 0.0062 (16) |
C19 | 0.051 (2) | 0.0459 (19) | 0.054 (2) | 0.0001 (16) | 0.0181 (17) | 0.0005 (16) |
C20 | 0.0432 (18) | 0.0447 (19) | 0.0362 (16) | 0.0051 (15) | 0.0101 (14) | −0.0053 (14) |
C21 | 0.057 (2) | 0.051 (2) | 0.055 (2) | 0.0015 (17) | 0.0231 (17) | −0.0065 (16) |
C22 | 0.060 (2) | 0.069 (3) | 0.062 (2) | 0.0031 (19) | 0.0282 (18) | −0.0050 (19) |
C23 | 0.066 (3) | 0.072 (3) | 0.058 (2) | 0.017 (2) | 0.0202 (19) | −0.0104 (19) |
C24 | 0.078 (3) | 0.045 (2) | 0.075 (2) | 0.007 (2) | 0.023 (2) | −0.0119 (19) |
C25 | 0.059 (2) | 0.044 (2) | 0.063 (2) | −0.0033 (17) | 0.0217 (18) | −0.0061 (17) |
Cl3' | 0.118 (4) | 0.060 (3) | 0.116 (4) | 0.003 (2) | 0.005 (3) | −0.021 (3) |
Cl4' | 0.154 (5) | 0.155 (4) | 0.118 (4) | −0.002 (4) | 0.011 (4) | −0.019 (3) |
Cl5' | 0.153 (4) | 0.128 (4) | 0.135 (4) | 0.003 (3) | 0.024 (3) | 0.028 (3) |
C26' | 0.097 (6) | 0.089 (6) | 0.090 (6) | 0.013 (5) | 0.022 (4) | 0.011 (5) |
Cl3 | 0.127 (2) | 0.126 (2) | 0.127 (2) | 0.0017 (11) | 0.0395 (12) | 0.0006 (11) |
Cl4 | 0.096 (5) | 0.094 (5) | 0.082 (4) | 0.014 (4) | 0.019 (3) | −0.002 (3) |
Cl5 | 0.137 (5) | 0.125 (5) | 0.110 (4) | −0.007 (4) | 0.019 (4) | −0.014 (4) |
C26 | 0.103 (8) | 0.087 (8) | 0.095 (8) | −0.003 (5) | 0.020 (5) | −0.007 (5) |
Cl1—C1 | 1.742 (3) | C21—C22 | 1.386 (4) |
Cl2—C5 | 1.741 (4) | C21—H21 | 0.9300 |
N1—C9 | 1.295 (4) | C22—C23 | 1.381 (5) |
N1—N2 | 1.373 (3) | C22—H22 | 0.9300 |
N2—C20 | 1.389 (4) | C23—C24 | 1.361 (5) |
N2—C7 | 1.481 (4) | C23—H23 | 0.9300 |
C1—C2 | 1.390 (4) | C24—C25 | 1.386 (5) |
C1—C6 | 1.398 (4) | C24—H24 | 0.9300 |
C2—C3 | 1.377 (5) | C25—H25 | 0.9300 |
C2—H2 | 0.9300 | Cl3'—Cl4'i | 1.098 (11) |
C3—C4 | 1.364 (5) | Cl3'—C26' | 1.825 (9) |
C3—H3 | 0.9300 | Cl3'—C26'i | 1.848 (12) |
C4—C5 | 1.382 (5) | Cl3'—Cl5'i | 2.365 (9) |
C4—H4 | 0.9300 | Cl4'—Cl3'i | 1.098 (11) |
C5—C6 | 1.400 (4) | Cl4'—C26'i | 1.408 (12) |
C6—C7 | 1.531 (4) | Cl4'—C26' | 1.773 (9) |
C7—C8 | 1.540 (4) | Cl4'—Cl5'i | 1.807 (11) |
C7—H7 | 0.9800 | Cl5'—C26' | 1.752 (9) |
C8—C9 | 1.507 (4) | Cl5'—Cl4'i | 1.807 (11) |
C8—H8A | 0.9700 | Cl5'—Cl3'i | 2.365 (9) |
C8—H8B | 0.9700 | C26'—Cl4'i | 1.408 (12) |
C9—C10 | 1.463 (4) | C26'—C26'i | 1.59 (2) |
C10—C11 | 1.371 (4) | C26'—Cl3'i | 1.848 (12) |
C10—C19 | 1.426 (4) | C26'—H26B | 0.9600 |
C11—C12 | 1.413 (4) | Cl3—Cl4i | 1.275 (13) |
C11—H11 | 0.9300 | Cl3—C26i | 1.600 (16) |
C12—C13 | 1.414 (4) | Cl3—C26 | 1.778 (10) |
C12—C17 | 1.428 (4) | Cl3—Cl5i | 1.977 (12) |
C13—C14 | 1.358 (5) | Cl4—Cl3i | 1.275 (13) |
C13—H13 | 0.9300 | Cl4—C26i | 1.421 (16) |
C14—C15 | 1.404 (5) | Cl4—C26 | 1.794 (10) |
C14—H14 | 0.9300 | Cl4—Cl5i | 1.994 (15) |
C15—C16 | 1.362 (5) | Cl5—C26 | 1.780 (11) |
C15—H15 | 0.9300 | Cl5—Cl3i | 1.977 (12) |
C16—C17 | 1.413 (5) | Cl5—Cl4i | 1.994 (15) |
C16—H16 | 0.9300 | Cl5—C26i | 2.021 (18) |
C17—C18 | 1.416 (4) | C26—C26i | 0.96 (3) |
C18—C19 | 1.361 (4) | C26—Cl4i | 1.421 (16) |
C18—H18 | 0.9300 | C26—Cl3i | 1.600 (16) |
C19—H19 | 0.9300 | C26—Cl5i | 2.021 (18) |
C20—C25 | 1.387 (4) | C26—H26A | 0.9601 |
C20—C21 | 1.392 (4) | ||
C9—N1—N2 | 109.3 (2) | C25—C20—N2 | 120.5 (3) |
N1—N2—C20 | 120.1 (2) | C25—C20—C21 | 118.5 (3) |
N1—N2—C7 | 112.8 (2) | N2—C20—C21 | 121.0 (3) |
C20—N2—C7 | 126.1 (3) | C22—C21—C20 | 120.5 (3) |
C2—C1—C6 | 122.4 (3) | C22—C21—H21 | 119.7 |
C2—C1—Cl1 | 117.0 (3) | C20—C21—H21 | 119.7 |
C6—C1—Cl1 | 120.6 (2) | C23—C22—C21 | 120.3 (3) |
C3—C2—C1 | 119.6 (4) | C23—C22—H22 | 119.9 |
C3—C2—H2 | 120.2 | C21—C22—H22 | 119.9 |
C1—C2—H2 | 120.2 | C24—C23—C22 | 119.3 (3) |
C4—C3—C2 | 119.9 (3) | C24—C23—H23 | 120.4 |
C4—C3—H3 | 120.1 | C22—C23—H23 | 120.4 |
C2—C3—H3 | 120.1 | C23—C24—C25 | 121.4 (3) |
C3—C4—C5 | 120.3 (4) | C23—C24—H24 | 119.3 |
C3—C4—H4 | 119.9 | C25—C24—H24 | 119.3 |
C5—C4—H4 | 119.9 | C24—C25—C20 | 120.1 (3) |
C4—C5—C6 | 122.4 (3) | C24—C25—H25 | 120.0 |
C4—C5—Cl2 | 116.3 (3) | C20—C25—H25 | 120.0 |
C6—C5—Cl2 | 121.3 (3) | Cl4'i—C26'—C26'i | 72.1 (8) |
C1—C6—C5 | 115.5 (3) | Cl4'i—C26'—Cl5' | 68.8 (6) |
C1—C6—C7 | 121.5 (3) | C26'i—C26'—Cl5' | 98.6 (10) |
C5—C6—C7 | 123.0 (3) | Cl4'i—C26'—Cl4' | 121.1 (9) |
N2—C7—C6 | 113.9 (2) | C26'i—C26'—Cl4' | 49.1 (6) |
N2—C7—C8 | 101.9 (2) | Cl5'—C26'—Cl4' | 115.0 (7) |
C6—C7—C8 | 114.2 (2) | Cl4'i—C26'—Cl3' | 36.9 (5) |
N2—C7—H7 | 108.9 | C26'i—C26'—Cl3' | 65.0 (6) |
C6—C7—H7 | 108.9 | Cl5'—C26'—Cl3' | 105.7 (6) |
C8—C7—H7 | 108.9 | Cl4'—C26'—Cl3' | 104.8 (6) |
C9—C8—C7 | 102.7 (2) | Cl4'i—C26'—Cl3'i | 121.5 (10) |
C9—C8—H8A | 111.2 | C26'i—C26'—Cl3'i | 63.5 (7) |
C7—C8—H8A | 111.2 | Cl5'—C26'—Cl3'i | 82.1 (5) |
C9—C8—H8B | 111.2 | Cl4'—C26'—Cl3'i | 35.2 (4) |
C7—C8—H8B | 111.2 | Cl3'—C26'—Cl3'i | 128.5 (7) |
H8A—C8—H8B | 109.1 | Cl4'i—C26'—H26B | 121.1 |
N1—C9—C10 | 122.2 (3) | C26'i—C26'—H26B | 144.8 |
N1—C9—C8 | 113.2 (3) | Cl5'—C26'—H26B | 116.6 |
C10—C9—C8 | 124.5 (3) | Cl4'—C26'—H26B | 109.0 |
C11—C10—C19 | 118.5 (3) | Cl3'—C26'—H26B | 104.5 |
C11—C10—C9 | 120.9 (3) | Cl3'i—C26'—H26B | 117.2 |
C19—C10—C9 | 120.6 (3) | C26i—C26—Cl4i | 95.9 (17) |
C10—C11—C12 | 122.5 (3) | C26i—C26—Cl3i | 84.1 (13) |
C10—C11—H11 | 118.7 | Cl4i—C26—Cl3i | 147.5 (12) |
C12—C11—H11 | 118.7 | C26i—C26—Cl3 | 63.5 (13) |
C11—C12—C13 | 122.7 (3) | Cl4i—C26—Cl3 | 45.3 (6) |
C11—C12—C17 | 118.4 (3) | Cl3i—C26—Cl3 | 147.6 (10) |
C13—C12—C17 | 118.8 (3) | C26i—C26—Cl5 | 90.0 (18) |
C14—C13—C12 | 121.0 (3) | Cl4i—C26—Cl5 | 76.1 (8) |
C14—C13—H13 | 119.5 | Cl3i—C26—Cl5 | 71.4 (6) |
C12—C13—H13 | 119.5 | Cl3—C26—Cl5 | 106.7 (9) |
C13—C14—C15 | 120.5 (4) | C26i—C26—Cl4 | 52.0 (12) |
C13—C14—H14 | 119.8 | Cl4i—C26—Cl4 | 147.9 (11) |
C15—C14—H14 | 119.8 | Cl3i—C26—Cl4 | 43.7 (5) |
C16—C15—C14 | 120.2 (4) | Cl3—C26—Cl4 | 108.6 (8) |
C16—C15—H15 | 119.9 | Cl5—C26—Cl4 | 100.9 (7) |
C14—C15—H15 | 119.9 | C26i—C26—Cl5i | 61.7 (13) |
C15—C16—C17 | 121.3 (3) | Cl4i—C26—Cl5i | 105.1 (9) |
C15—C16—H16 | 119.3 | Cl3i—C26—Cl5i | 103.4 (7) |
C17—C16—H16 | 119.3 | Cl3—C26—Cl5i | 62.3 (5) |
C16—C17—C18 | 123.6 (3) | Cl5—C26—Cl5i | 151.7 (10) |
C16—C17—C12 | 118.2 (3) | Cl4—C26—Cl5i | 62.7 (5) |
C18—C17—C12 | 118.2 (3) | C26i—C26—H26A | 152.5 |
C19—C18—C17 | 122.0 (3) | Cl4i—C26—H26A | 91.3 |
C19—C18—H18 | 119.0 | Cl3i—C26—H26A | 103.6 |
C17—C18—H18 | 119.0 | Cl3—C26—H26A | 105.4 |
C18—C19—C10 | 120.4 (3) | Cl5—C26—H26A | 117.5 |
C18—C19—H19 | 119.8 | Cl4—C26—H26A | 117.1 |
C10—C19—H19 | 119.8 | Cl5i—C26—H26A | 90.8 |
C9—N1—N2—C20 | −171.8 (3) | C8—C9—C10—C19 | −177.8 (3) |
C9—N1—N2—C7 | −3.0 (3) | C19—C10—C11—C12 | −0.4 (4) |
C6—C1—C2—C3 | 0.5 (5) | C9—C10—C11—C12 | −179.0 (3) |
Cl1—C1—C2—C3 | −179.7 (3) | C10—C11—C12—C13 | 178.4 (3) |
C1—C2—C3—C4 | −0.7 (6) | C10—C11—C12—C17 | −1.2 (4) |
C2—C3—C4—C5 | −0.1 (6) | C11—C12—C13—C14 | −179.7 (3) |
C3—C4—C5—C6 | 1.2 (6) | C17—C12—C13—C14 | −0.1 (5) |
C3—C4—C5—Cl2 | −176.0 (3) | C12—C13—C14—C15 | −1.4 (5) |
C2—C1—C6—C5 | 0.5 (5) | C13—C14—C15—C16 | 1.7 (6) |
Cl1—C1—C6—C5 | −179.3 (2) | C14—C15—C16—C17 | −0.5 (5) |
C2—C1—C6—C7 | 178.7 (3) | C15—C16—C17—C18 | 178.5 (3) |
Cl1—C1—C6—C7 | −1.0 (4) | C15—C16—C17—C12 | −1.0 (5) |
C4—C5—C6—C1 | −1.4 (5) | C11—C12—C17—C16 | −179.1 (3) |
Cl2—C5—C6—C1 | 175.7 (2) | C13—C12—C17—C16 | 1.3 (4) |
C4—C5—C6—C7 | −179.6 (3) | C11—C12—C17—C18 | 1.4 (4) |
Cl2—C5—C6—C7 | −2.5 (4) | C13—C12—C17—C18 | −178.2 (3) |
N1—N2—C7—C6 | 125.5 (3) | C16—C17—C18—C19 | −179.3 (3) |
C20—N2—C7—C6 | −66.5 (4) | C12—C17—C18—C19 | 0.2 (5) |
N1—N2—C7—C8 | 2.1 (3) | C17—C18—C19—C10 | −1.9 (5) |
C20—N2—C7—C8 | 170.1 (3) | C11—C10—C19—C18 | 2.0 (4) |
C1—C6—C7—N2 | 131.1 (3) | C9—C10—C19—C18 | −179.4 (3) |
C5—C6—C7—N2 | −50.7 (4) | N1—N2—C20—C25 | −9.2 (4) |
C1—C6—C7—C8 | −112.4 (3) | C7—N2—C20—C25 | −176.4 (3) |
C5—C6—C7—C8 | 65.7 (4) | N1—N2—C20—C21 | 172.4 (3) |
N2—C7—C8—C9 | −0.5 (3) | C7—N2—C20—C21 | 5.2 (4) |
C6—C7—C8—C9 | −123.7 (3) | C25—C20—C21—C22 | 0.5 (4) |
N2—N1—C9—C10 | −175.8 (2) | N2—C20—C21—C22 | 178.9 (3) |
N2—N1—C9—C8 | 2.6 (3) | C20—C21—C22—C23 | −0.2 (5) |
C7—C8—C9—N1 | −1.2 (3) | C21—C22—C23—C24 | 0.4 (5) |
C7—C8—C9—C10 | 177.2 (3) | C22—C23—C24—C25 | −0.7 (5) |
N1—C9—C10—C11 | 179.0 (3) | C23—C24—C25—C20 | 1.0 (5) |
C8—C9—C10—C11 | 0.7 (4) | N2—C20—C25—C24 | −179.3 (3) |
N1—C9—C10—C19 | 0.5 (4) | C21—C20—C25—C24 | −0.9 (4) |
Symmetry code: (i) −x+1, −y+1, −z+1. |