Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807004023/ww2065sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807004023/ww2065Isup2.hkl |
CCDC reference: 640521
Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS86 (Sheldrick, 1985); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).
C24H26Cl3N3O2S | F(000) = 1096 |
Mr = 526.89 | Dx = 1.369 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 13171 reflections |
a = 9.3870 (2) Å | θ = 2.4–25.0° |
b = 14.9382 (3) Å | µ = 0.47 mm−1 |
c = 18.2241 (4) Å | T = 293 K |
V = 2555.47 (9) Å3 | Prism, yellow |
Z = 4 | 0.5 × 0.4 × 0.2 mm |
Rigaku R-AXIS RAPID-S area-detector diffractometer | Rint = 0.083 |
ω scans | θmax = 25.1°, θmin = 2.6° |
49160 measured reflections | h = −10→11 |
4516 independent reflections | k = −17→17 |
4486 reflections with I > 2σ(I) | l = −21→21 |
Refinement on F2 | H atoms treated by a mixture of independent and constrained refinement |
Least-squares matrix: full | w = 1/[σ2(Fo2) + 5.2662P] where P = (Fo2 + 2Fc2)/3 |
R[F2 > 2σ(F2)] = 0.099 | (Δ/σ)max = 0.09 |
wR(F2) = 0.173 | Δρmax = 0.34 e Å−3 |
S = 1.54 | Δρmin = −0.29 e Å−3 |
4516 reflections | Absolute structure: Flack (1983), with 1945 Friedel pairs |
303 parameters | Absolute structure parameter: 0.08 (15) |
0 restraints |
Geometry. Least Squares Planes ————– Plane number 1 ————— Atoms Defining Plane Distance e.s.d. C21 [1;0;0;0] -0.1452 0.0029 C20 [1;0;0;0] 0.2043 0.0040 C19 [1;0;0;0] -0.1770 0.0035 C18 [1;0;0;0] 0.0719 0.0014 Mean deviation from plane is 0.1496 angstrom Chi-squared: 2461.373 ————– Plane number 2 ————— Atoms Defining Plane Distance e.s.d. S1 [1;0;0;0] 0.0011 0.0002 C22 [1;0;0;0] -0.0147 0.0029 C23 [1;0;0;0] -0.0249 0.0050 C24 [1;0;0;0] 0.0330 0.0066 Mean deviation from plane is 0.0185 angstrom Chi-squared: 35.489 ————– Plane number 3 ————— Atoms Defining Plane Distance e.s.d. C14 [1;0;0;0] -0.0093 0.0038 C15 [1;0;0;0] 0.0082 0.0033 C16 [1;0;0;0] -0.0070 0.0028 C17 [1;0;0;0] 0.0071 0.0029 Additional Atoms Distance e.s.d. N2 (1) 0.6399 0.0081 N1 (1) -0.6919 0.0078 Mean deviation from plane is 0.0079 angstrom Chi-squared: 6.246 ————– Plane number 4 ————— Atoms Defining Plane Distance e.s.d. C1 [1;0;0;0] 0.0050 0.0042 C2 [1;0;0;0] -0.0036 0.0047 C3 [1;0;0;0] 0.0015 0.0069 C4 [1;0;0;0] -0.0008 0.0074 C5 [1;0;0;0] 0.0044 0.0066 C6 [1;0;0;0] -0.0066 0.0055 Mean deviation from plane is 0.0037 angstrom Chi-squared: 1.499 ————– Plane number 5 ————— Atoms Defining Plane Distance e.s.d. C8 [1;0;0;0] -0.0006 0.0038 C9 [1;0;0;0] -0.0005 0.0063 C10 [1;0;0;0] 0.0057 0.0076 C11 [1;0;0;0] -0.0078 0.0072 C12 [1;0;0;0] 0.0051 0.0068 C13 [1;0;0;0] -0.0006 0.0052 Mean deviation from plane is 0.0034 angstrom Chi-squared: 1.584 Dihedral angles between least-squares planes ——————————————– plane plane angle e.s.d. 1 2 128.814 0.374 1 3 67.172 0.293 1 4 12.964 0.310 1 5 80.832 0.364 2 3 89.971 0.569 2 4 124.525 0.425 2 5 49.374 0.246 3 4 54.269 0.269 3 5 79.752 0.307 4 5 80.598 0.282 |
x | y | z | Uiso*/Ueq | ||
Cl1 | 0.8753 (2) | 0.78769 (14) | −0.07266 (13) | 0.0676 (6) | |
Cl3 | 0.7612 (3) | 0.54162 (16) | −0.17899 (12) | 0.0768 (7) | |
S1 | 1.0701 (2) | 0.58886 (16) | −0.00832 (12) | 0.0605 (6) | |
Cl2 | 0.8941 (3) | 0.7272 (2) | −0.22162 (13) | 0.0885 (8) | |
N1 | 0.8916 (6) | 0.7273 (4) | 0.2165 (3) | 0.0486 (15) | |
N2 | 0.8679 (7) | 0.6201 (4) | 0.0858 (3) | 0.0527 (16) | |
O1 | 0.6241 (7) | 0.5250 (4) | 0.0414 (3) | 0.0757 (18) | |
O2 | 0.5428 (6) | 0.5822 (5) | −0.0595 (4) | 0.0824 (19) | |
N3 | 0.6413 (7) | 0.5672 (4) | −0.0162 (4) | 0.0580 (17) | |
C18 | 0.8892 (7) | 0.5999 (4) | 0.0151 (4) | 0.0441 (17) | |
C14 | 0.8041 (8) | 0.7542 (5) | 0.1546 (4) | 0.0490 (19) | |
H14A | 0.8598 | 0.7923 | 0.1225 | 0.059* | |
H14B | 0.7239 | 0.7889 | 0.1724 | 0.059* | |
C20 | 0.7983 (8) | 0.6219 (5) | −0.1118 (4) | 0.0476 (19) | |
C19 | 0.7803 (7) | 0.5969 (5) | −0.0366 (4) | 0.0450 (17) | |
C17 | 0.9614 (9) | 0.5934 (6) | 0.1473 (4) | 0.061 (2) | |
H17A | 1.0426 | 0.5603 | 0.1286 | 0.074* | |
H17B | 0.9094 | 0.5547 | 0.1807 | 0.074* | |
C8 | 0.8283 (8) | 0.8716 (5) | 0.2784 (4) | 0.0461 (18) | |
C7 | 0.9442 (9) | 0.8023 (5) | 0.2609 (4) | 0.051 (2) | |
C21 | 0.8463 (9) | 0.7007 (6) | −0.1336 (4) | 0.058 (2) | |
C6 | 1.0184 (8) | 0.7698 (5) | 0.3301 (4) | 0.0507 (19) | |
C15 | 0.7485 (8) | 0.6748 (5) | 0.1108 (4) | 0.0517 (19) | |
H15A | 0.6857 | 0.6391 | 0.1413 | 0.062* | |
H15B | 0.6945 | 0.696 | 0.0689 | 0.062* | |
C16 | 1.0120 (9) | 0.6749 (6) | 0.1877 (4) | 0.059 (2) | |
H16A | 1.0731 | 0.6568 | 0.228 | 0.07* | |
H16B | 1.0678 | 0.712 | 0.1547 | 0.07* | |
C22 | 1.0767 (9) | 0.5031 (5) | −0.0784 (4) | 0.062 (2) | |
H22A | 1.0289 | 0.5253 | −0.122 | 0.074* | |
H22B | 1.1755 | 0.4923 | −0.0912 | 0.074* | |
C23 | 1.0092 (12) | 0.4153 (7) | −0.0565 (6) | 0.086 (3) | |
H23A | 0.9114 | 0.4257 | −0.0416 | 0.103* | |
H23B | 1.0602 | 0.3905 | −0.0149 | 0.103* | |
C1 | 0.9776 (10) | 0.6930 (6) | 0.3650 (5) | 0.068 (3) | |
H023 | 0.9045 | 0.6586 | 0.3452 | 0.082* | |
C5 | 1.1240 (9) | 0.8213 (6) | 0.3608 (4) | 0.062 (2) | |
H024 | 1.1509 | 0.8744 | 0.338 | 0.075* | |
C2 | 1.0434 (12) | 0.6649 (7) | 0.4301 (5) | 0.084 (3) | |
H025 | 1.016 | 0.6122 | 0.4532 | 0.101* | |
C11 | 0.6206 (13) | 0.9941 (8) | 0.3140 (7) | 0.100 (4) | |
H026 | 0.551 | 1.0359 | 0.3263 | 0.12* | |
C9 | 0.7283 (12) | 0.8529 (7) | 0.3300 (6) | 0.087 (3) | |
H027 | 0.7305 | 0.7978 | 0.3537 | 0.104* | |
C13 | 0.8253 (10) | 0.9527 (6) | 0.2432 (5) | 0.067 (2) | |
H028 | 0.8927 | 0.9665 | 0.2075 | 0.08* | |
C12 | 0.7202 (11) | 1.0137 (7) | 0.2616 (7) | 0.088 (3) | |
H029 | 0.7172 | 1.0688 | 0.238 | 0.106* | |
C24 | 1.0117 (14) | 0.3483 (6) | −0.1197 (6) | 0.096 (4) | |
H24A | 0.949 | 0.3684 | −0.1579 | 0.145* | |
H24B | 0.9809 | 0.2908 | −0.1023 | 0.145* | |
H24C | 1.1069 | 0.3436 | −0.1386 | 0.145* | |
C3 | 1.1508 (13) | 0.7182 (8) | 0.4591 (5) | 0.090 (4) | |
H031 | 1.1964 | 0.7013 | 0.5022 | 0.108* | |
C10 | 0.6240 (13) | 0.9136 (9) | 0.3479 (6) | 0.102 (4) | |
H032 | 0.556 | 0.8994 | 0.3831 | 0.122* | |
C4 | 1.1896 (10) | 0.7960 (8) | 0.4239 (5) | 0.082 (3) | |
H033 | 1.2615 | 0.8315 | 0.4435 | 0.098* | |
H7 | 1.003 (5) | 0.835 (3) | 0.232 (3) | 0.000 (11)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0630 (13) | 0.0523 (11) | 0.0874 (15) | −0.0051 (11) | 0.0071 (12) | 0.0006 (11) |
Cl3 | 0.0982 (18) | 0.0771 (15) | 0.0552 (12) | 0.0060 (14) | −0.0220 (13) | −0.0172 (12) |
S1 | 0.0449 (10) | 0.0799 (15) | 0.0567 (13) | 0.0036 (11) | −0.0026 (10) | −0.0186 (12) |
Cl2 | 0.0895 (19) | 0.118 (2) | 0.0580 (13) | −0.0005 (17) | 0.0111 (13) | 0.0252 (14) |
N1 | 0.049 (4) | 0.054 (4) | 0.043 (3) | 0.005 (3) | 0.002 (3) | −0.004 (3) |
N2 | 0.051 (4) | 0.052 (4) | 0.055 (4) | 0.015 (3) | −0.004 (3) | −0.006 (3) |
O1 | 0.088 (5) | 0.070 (4) | 0.070 (4) | −0.031 (4) | 0.010 (4) | 0.002 (3) |
O2 | 0.051 (4) | 0.105 (5) | 0.092 (5) | −0.004 (4) | −0.015 (4) | −0.002 (4) |
N3 | 0.054 (4) | 0.048 (4) | 0.072 (5) | −0.004 (3) | −0.009 (4) | −0.014 (4) |
C18 | 0.050 (4) | 0.037 (4) | 0.045 (4) | 0.003 (3) | 0.013 (3) | −0.003 (3) |
C14 | 0.041 (4) | 0.062 (5) | 0.044 (4) | 0.003 (4) | 0.011 (3) | −0.004 (4) |
C20 | 0.051 (5) | 0.041 (4) | 0.051 (5) | 0.010 (4) | −0.007 (4) | −0.006 (4) |
C19 | 0.043 (4) | 0.047 (4) | 0.046 (4) | −0.007 (4) | −0.003 (3) | −0.012 (4) |
C17 | 0.073 (6) | 0.063 (5) | 0.048 (5) | 0.025 (5) | −0.012 (4) | −0.019 (4) |
C8 | 0.046 (4) | 0.055 (5) | 0.037 (4) | 0.003 (4) | 0.002 (3) | −0.019 (4) |
C7 | 0.067 (5) | 0.055 (5) | 0.030 (4) | −0.026 (4) | 0.014 (4) | 0.005 (3) |
C21 | 0.050 (5) | 0.080 (6) | 0.044 (4) | 0.023 (5) | −0.001 (4) | 0.007 (4) |
C6 | 0.057 (5) | 0.056 (5) | 0.038 (4) | 0.002 (4) | 0.011 (4) | −0.006 (4) |
C15 | 0.047 (4) | 0.053 (5) | 0.054 (5) | 0.002 (4) | 0.000 (4) | −0.009 (4) |
C16 | 0.061 (5) | 0.073 (6) | 0.042 (4) | 0.026 (5) | −0.003 (4) | −0.002 (4) |
C22 | 0.060 (5) | 0.068 (5) | 0.057 (5) | 0.011 (5) | 0.006 (4) | −0.019 (4) |
C23 | 0.098 (7) | 0.078 (7) | 0.080 (7) | 0.014 (6) | 0.019 (6) | −0.008 (6) |
C1 | 0.082 (7) | 0.068 (6) | 0.054 (5) | −0.002 (5) | 0.002 (5) | 0.004 (5) |
C5 | 0.064 (5) | 0.069 (6) | 0.055 (5) | 0.013 (5) | 0.005 (4) | −0.004 (4) |
C2 | 0.110 (9) | 0.088 (7) | 0.054 (6) | 0.010 (7) | 0.011 (6) | 0.023 (5) |
C11 | 0.085 (8) | 0.089 (8) | 0.125 (10) | 0.036 (7) | −0.031 (8) | −0.073 (8) |
C9 | 0.098 (8) | 0.077 (7) | 0.086 (7) | 0.030 (6) | 0.009 (7) | 0.008 (6) |
C13 | 0.074 (6) | 0.057 (5) | 0.070 (6) | −0.004 (5) | −0.024 (5) | 0.006 (5) |
C12 | 0.069 (7) | 0.065 (7) | 0.130 (10) | 0.007 (6) | −0.037 (7) | −0.012 (7) |
C24 | 0.138 (10) | 0.057 (6) | 0.094 (8) | 0.018 (7) | 0.008 (7) | −0.018 (6) |
C3 | 0.113 (9) | 0.113 (9) | 0.045 (5) | 0.042 (8) | −0.013 (6) | 0.002 (6) |
C10 | 0.095 (9) | 0.119 (10) | 0.091 (8) | 0.038 (9) | 0.015 (7) | −0.014 (8) |
C4 | 0.073 (6) | 0.109 (8) | 0.064 (6) | 0.013 (6) | −0.018 (5) | −0.018 (6) |
Cl1—C21 | 1.731 (9) | C15—H15B | 0.97 |
Cl3—C20 | 1.749 (7) | C16—H16A | 0.97 |
S1—C18 | 1.759 (7) | C16—H16B | 0.97 |
S1—C22 | 1.810 (7) | C22—C23 | 1.510 (9) |
Cl2—C21 | 1.712 (8) | C22—H22A | 0.97 |
N1—C14 | 1.452 (9) | C22—H22B | 0.97 |
N1—C7 | 1.468 (9) | C23—C24 | 1.526 (9) |
N1—C16 | 1.472 (9) | C23—H23A | 0.97 |
N2—C18 | 1.337 (9) | C23—H23B | 0.97 |
N2—C15 | 1.461 (9) | C1—C2 | 1.401 (9) |
N2—C17 | 1.480 (9) | C1—H023 | 0.93 |
O1—N3 | 1.235 (8) | C5—C4 | 1.359 (9) |
O2—N3 | 1.236 (8) | C5—H024 | 0.93 |
N3—C19 | 1.427 (9) | C2—C3 | 1.388 (9) |
C18—C19 | 1.391 (9) | C2—H025 | 0.93 |
C14—C15 | 1.521 (9) | C11—C10 | 1.353 (9) |
C14—H14A | 0.97 | C11—C12 | 1.368 (9) |
C14—H14B | 0.97 | C11—H026 | 0.93 |
C20—C21 | 1.321 (9) | C9—C10 | 1.374 (9) |
C20—C19 | 1.432 (9) | C9—H027 | 0.93 |
C17—C16 | 1.500 (9) | C13—C12 | 1.384 (9) |
C17—H17A | 0.97 | C13—H028 | 0.93 |
C17—H17B | 0.97 | C12—H029 | 0.93 |
C8—C9 | 1.357 (9) | C24—H24A | 0.96 |
C8—C13 | 1.371 (9) | C24—H24B | 0.96 |
C8—C7 | 1.536 (9) | C24—H24C | 0.96 |
C7—C6 | 1.519 (9) | C3—C4 | 1.376 (9) |
C7—H7 | 0.90 (5) | C3—H031 | 0.93 |
C6—C1 | 1.367 (9) | C10—H032 | 0.93 |
C6—C5 | 1.374 (9) | C4—H033 | 0.93 |
C15—H15A | 0.97 | ||
C18—S1—C22 | 105.7 (4) | N1—C16—H16A | 109.4 |
C14—N1—C7 | 114.1 (6) | C17—C16—H16A | 109.4 |
C14—N1—C16 | 107.7 (6) | N1—C16—H16B | 109.4 |
C7—N1—C16 | 110.1 (6) | C17—C16—H16B | 109.4 |
C18—N2—C15 | 122.9 (6) | H16A—C16—H16B | 108 |
C18—N2—C17 | 125.5 (6) | C23—C22—S1 | 114.5 (6) |
C15—N2—C17 | 111.6 (6) | C23—C22—H22A | 108.6 |
O1—N3—O2 | 122.5 (7) | S1—C22—H22A | 108.6 |
O1—N3—C19 | 119.9 (7) | C23—C22—H22B | 108.6 |
O2—N3—C19 | 117.5 (7) | S1—C22—H22B | 108.6 |
N2—C18—C19 | 123.3 (6) | H22A—C22—H22B | 107.6 |
N2—C18—S1 | 113.6 (6) | C22—C23—C24 | 111.3 (8) |
C19—C18—S1 | 122.8 (5) | C22—C23—H23A | 109.4 |
N1—C14—C15 | 112.7 (6) | C24—C23—H23A | 109.4 |
N1—C14—H14A | 109.1 | C22—C23—H23B | 109.4 |
C15—C14—H14A | 109.1 | C24—C23—H23B | 109.4 |
N1—C14—H14B | 109.1 | H23A—C23—H23B | 108 |
C15—C14—H14B | 109.1 | C6—C1—C2 | 121.4 (10) |
H14A—C14—H14B | 107.8 | C6—C1—H023 | 119.3 |
C21—C20—C19 | 124.1 (7) | C2—C1—H023 | 119.3 |
C21—C20—Cl3 | 118.0 (6) | C4—C5—C6 | 121.0 (9) |
C19—C20—Cl3 | 117.9 (6) | C4—C5—H024 | 119.5 |
C18—C19—N3 | 120.4 (7) | C6—C5—H024 | 119.5 |
C18—C19—C20 | 123.6 (7) | C3—C2—C1 | 118.1 (10) |
N3—C19—C20 | 116.0 (7) | C3—C2—H025 | 120.9 |
N2—C17—C16 | 109.9 (6) | C1—C2—H025 | 120.9 |
N2—C17—H17A | 109.7 | C10—C11—C12 | 119.5 (10) |
C16—C17—H17A | 109.7 | C10—C11—H026 | 120.3 |
N2—C17—H17B | 109.7 | C12—C11—H026 | 120.3 |
C16—C17—H17B | 109.7 | C8—C9—C10 | 121.4 (10) |
H17A—C17—H17B | 108.2 | C8—C9—H027 | 119.3 |
C9—C8—C13 | 119.5 (8) | C10—C9—H027 | 119.3 |
C9—C8—C7 | 119.6 (8) | C8—C13—C12 | 118.8 (10) |
C13—C8—C7 | 120.9 (7) | C8—C13—H028 | 120.6 |
N1—C7—C6 | 111.6 (6) | C12—C13—H028 | 120.6 |
N1—C7—C8 | 112.9 (6) | C11—C12—C13 | 121.1 (11) |
C6—C7—C8 | 111.7 (6) | C11—C12—H029 | 119.4 |
N1—C7—H7 | 108 (3) | C13—C12—H029 | 119.4 |
C6—C7—H7 | 112 (3) | C23—C24—H24A | 109.5 |
C8—C7—H7 | 101 (3) | C23—C24—H24B | 109.5 |
C20—C21—Cl2 | 125.2 (7) | H24A—C24—H24B | 109.5 |
C20—C21—Cl1 | 122.0 (6) | C23—C24—H24C | 109.5 |
Cl2—C21—Cl1 | 112.7 (5) | H24A—C24—H24C | 109.5 |
C1—C6—C5 | 118.9 (8) | H24B—C24—H24C | 109.5 |
C1—C6—C7 | 121.8 (8) | C4—C3—C2 | 119.9 (9) |
C5—C6—C7 | 119.3 (7) | C4—C3—H031 | 120 |
N2—C15—C14 | 109.7 (6) | C2—C3—H031 | 120 |
N2—C15—H15A | 109.7 | C11—C10—C9 | 119.7 (12) |
C14—C15—H15A | 109.7 | C11—C10—H032 | 120.2 |
N2—C15—H15B | 109.7 | C9—C10—H032 | 120.2 |
C14—C15—H15B | 109.7 | C5—C4—C3 | 120.6 (10) |
H15A—C15—H15B | 108.2 | C5—C4—H033 | 119.7 |
N1—C16—C17 | 111.3 (7) | C3—C4—H033 | 119.7 |
C15—N2—C18—C19 | −25.8 (11) | Cl3—C20—C21—Cl2 | −7.6 (10) |
C17—N2—C18—C19 | 156.2 (8) | C19—C20—C21—Cl1 | −7.1 (12) |
C15—N2—C18—S1 | 147.9 (6) | Cl3—C20—C21—Cl1 | 175.6 (4) |
C17—N2—C18—S1 | −30.1 (10) | N1—C7—C6—C1 | −31.9 (10) |
C22—S1—C18—N2 | 146.5 (6) | C8—C7—C6—C1 | 95.6 (9) |
C22—S1—C18—C19 | −39.8 (7) | N1—C7—C6—C5 | 151.9 (7) |
C7—N1—C14—C15 | −178.7 (6) | C8—C7—C6—C5 | −80.7 (9) |
C16—N1—C14—C15 | 58.8 (8) | C18—N2—C15—C14 | −124.3 (7) |
N2—C18—C19—N3 | −34.4 (11) | C17—N2—C15—C14 | 53.9 (8) |
S1—C18—C19—N3 | 152.4 (6) | N1—C14—C15—N2 | −56.8 (8) |
N2—C18—C19—C20 | 146.0 (7) | C14—N1—C16—C17 | −59.9 (8) |
S1—C18—C19—C20 | −27.1 (10) | C7—N1—C16—C17 | 175.2 (6) |
O1—N3—C19—C18 | −16.8 (10) | N2—C17—C16—N1 | 59.0 (9) |
O2—N3—C19—C18 | 166.2 (7) | C18—S1—C22—C23 | −55.2 (8) |
O1—N3—C19—C20 | 162.8 (7) | S1—C22—C23—C24 | 176.9 (7) |
O2—N3—C19—C20 | −14.2 (10) | C5—C6—C1—C2 | −1.6 (13) |
C21—C20—C19—C18 | −56.0 (11) | C7—C6—C1—C2 | −177.9 (8) |
Cl3—C20—C19—C18 | 121.3 (7) | C1—C6—C5—C4 | 1.5 (12) |
C21—C20—C19—N3 | 124.5 (8) | C7—C6—C5—C4 | 177.9 (8) |
Cl3—C20—C19—N3 | −58.2 (8) | C6—C1—C2—C3 | 0.9 (14) |
C18—N2—C17—C16 | 122.3 (8) | C13—C8—C9—C10 | −0.1 (15) |
C15—N2—C17—C16 | −55.9 (9) | C7—C8—C9—C10 | 179.1 (9) |
C14—N1—C7—C6 | 172.6 (6) | C9—C8—C13—C12 | 0.3 (13) |
C16—N1—C7—C6 | −66.2 (8) | C7—C8—C13—C12 | −178.9 (7) |
C14—N1—C7—C8 | 45.8 (8) | C10—C11—C12—C13 | −0.6 (16) |
C16—N1—C7—C8 | 167.0 (6) | C8—C13—C12—C11 | 0.1 (14) |
C9—C8—C7—N1 | 75.5 (9) | C1—C2—C3—C4 | 0.0 (15) |
C13—C8—C7—N1 | −105.3 (8) | C12—C11—C10—C9 | 0.8 (17) |
C9—C8—C7—C6 | −51.2 (10) | C8—C9—C10—C11 | −0.5 (18) |
C13—C8—C7—C6 | 127.9 (8) | C6—C5—C4—C3 | −0.6 (14) |
C19—C20—C21—Cl2 | 169.7 (6) | C2—C3—C4—C5 | −0.1 (16) |