Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805004435/ob6482sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805004435/ob6482Isup2.hkl |
CCDC reference: 269842
Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC and Rigaku, 2004); program(s) used to solve structure: SIR2002 (Burla et al., 2003); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-III (Burnett & Johnson, 1996); software used to prepare material for publication: CrystalStructure.
C44H38N4·2CHCl3 | F(000) = 892.00 |
Mr = 861.52 | Dx = 1.427 Mg m−3 |
Monoclinic, P21/c | Cu Kα radiation, λ = 1.5418 Å |
Hall symbol: -P 2ybc | Cell parameters from 9212 reflections |
a = 10.282 (2) Å | θ = 4.5–68.0° |
b = 17.433 (3) Å | µ = 4.22 mm−1 |
c = 11.664 (2) Å | T = 93 K |
β = 106.51 (1)° | Block, dark red |
V = 2004.5 (6) Å3 | 0.20 × 0.20 × 0.20 mm |
Z = 2 |
Rigaku R-AXIS RAPID diffractometer | 1286 reflections with F2 > 2σ(F2) |
Detector resolution: 10.00 pixels mm-1 | Rint = 0.183 |
48 frames, δ ω = 15° scans | θmax = 68.2° |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | h = −11→11 |
Tmin = 0.400, Tmax = 0.430 | k = −20→20 |
18024 measured reflections | l = −13→14 |
3592 independent reflections |
Refinement on F2 | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.125 | w = 1/[σ2(Fo2) + (0.1P)2] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.311 | (Δ/σ)max < 0.001 |
S = 1.32 | Δρmax = 0.92 e Å−3 |
3592 reflections | Δρmin = −0.67 e Å−3 |
254 parameters |
Geometry. ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY |
Refinement. Refinement using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F2. R-factor (gt) are based on F. The threshold expression of F2 > 2.0 σ(F2) is used only for calculating R-factor (gt). |
x | y | z | Uiso*/Ueq | ||
Cl1 | 0.4440 (2) | −0.0242 (1) | 0.1270 (2) | 0.0961 (9) | |
Cl2 | 0.2157 (2) | −0.1016 (1) | 0.1748 (2) | 0.0933 (9) | |
Cl3 | 0.3934 (2) | −0.0097 (1) | 0.3548 (2) | 0.0707 (7) | |
N1 | −0.0576 (5) | 0.0457 (3) | 0.1475 (4) | 0.039 (1) | |
N2 | 0.1182 (5) | 0.0941 (3) | 0.0037 (4) | 0.035 (1) | |
C1 | 0.0740 (6) | 0.1650 (3) | 0.1707 (5) | 0.032 (1) | |
C2 | 0.1376 (6) | 0.1558 (3) | 0.0801 (5) | 0.034 (1) | |
C3 | 0.2349 (6) | 0.2085 (3) | 0.0554 (5) | 0.038 (2) | |
C4 | 0.2768 (6) | 0.1780 (3) | −0.0364 (5) | 0.033 (1) | |
C5 | 0.2019 (7) | 0.1073 (3) | −0.0686 (5) | 0.036 (1) | |
C6 | 0.3068 (6) | 0.2806 (3) | 0.1063 (5) | 0.040 (2) | |
C7 | 0.4618 (6) | 0.2576 (4) | 0.1540 (5) | 0.042 (2) | |
C8 | 0.5097 (6) | 0.2208 (4) | 0.0546 (5) | 0.041 (2) | |
C9 | 0.3902 (6) | 0.2208 (3) | −0.0641 (5) | 0.040 (2) | |
C10 | 0.3048 (6) | 0.3340 (3) | 0.0036 (5) | 0.041 (2) | |
C11 | 0.3466 (6) | 0.3028 (3) | −0.0847 (5) | 0.037 (2) | |
C12 | −0.0113 (6) | 0.1145 (3) | 0.2027 (5) | 0.038 (2) | |
C13 | −0.0715 (6) | 0.1197 (3) | 0.3002 (5) | 0.036 (1) | |
C14 | −0.1480 (6) | 0.0568 (3) | 0.3003 (5) | 0.035 (1) | |
C15 | −0.1428 (6) | 0.0088 (3) | 0.2018 (5) | 0.035 (1) | |
C16 | −0.0729 (6) | 0.1782 (3) | 0.3954 (5) | 0.038 (2) | |
C17 | −0.2249 (7) | 0.1988 (3) | 0.3731 (6) | 0.049 (2) | |
C18 | −0.3096 (6) | 0.1278 (3) | 0.3755 (5) | 0.042 (2) | |
C19 | −0.2210 (6) | 0.0548 (3) | 0.3952 (5) | 0.041 (2) | |
C20 | −0.0365 (7) | 0.1324 (4) | 0.5148 (5) | 0.044 (2) | |
C21 | −0.1123 (6) | 0.0687 (4) | 0.5142 (5) | 0.045 (2) | |
C22 | −0.2089 (6) | −0.0599 (3) | 0.1641 (5) | 0.039 (2) | |
C23 | 0.3160 (7) | −0.0196 (4) | 0.1996 (6) | 0.056 (2) | |
H1 | −0.0335 | 0.0261 | 0.0803 | 0.047* | |
H2 | 0.0921 | 0.2115 | 0.2148 | 0.038* | |
H3 | 0.2723 | 0.3034 | 0.1657 | 0.048* | |
H4 | 0.4154 | 0.1993 | −0.1295 | 0.048* | |
H5 | 0.5143 | 0.3022 | 0.1819 | 0.050* | |
H6 | 0.4732 | 0.2221 | 0.2180 | 0.050* | |
H7 | 0.5376 | 0.1695 | 0.0759 | 0.049* | |
H8 | 0.5838 | 0.2492 | 0.0430 | 0.049* | |
H9 | 0.2760 | 0.3859 | 0.0018 | 0.049* | |
H10 | 0.3484 | 0.3303 | −0.1545 | 0.045* | |
H11 | −0.2712 | 0.0089 | 0.3945 | 0.050* | |
H12 | −0.0161 | 0.2213 | 0.3962 | 0.046* | |
H13 | −0.3782 | 0.1236 | 0.3015 | 0.050* | |
H14 | −0.3505 | 0.1324 | 0.4387 | 0.050* | |
H15 | −0.2337 | 0.2333 | 0.4336 | 0.059* | |
H16 | −0.2571 | 0.2228 | 0.2971 | 0.059* | |
H17 | −0.0993 | 0.0357 | 0.5813 | 0.054* | |
H18 | 0.0338 | 0.1479 | 0.5830 | 0.053* | |
H19 | −0.2657 | −0.0770 | 0.2081 | 0.046* | |
H20 | 0.2604 | 0.0239 | 0.1715 | 0.067* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.086 (2) | 0.156 (2) | 0.056 (1) | 0.036 (2) | 0.035 (1) | 0.022 (1) |
Cl2 | 0.084 (2) | 0.073 (2) | 0.099 (2) | −0.009 (1) | −0.013 (1) | −0.018 (1) |
Cl3 | 0.082 (2) | 0.082 (1) | 0.051 (1) | −0.015 (1) | 0.023 (1) | −0.0153 (9) |
N1 | 0.046 (3) | 0.038 (3) | 0.034 (3) | −0.002 (3) | 0.015 (2) | −0.002 (2) |
N2 | 0.038 (3) | 0.036 (3) | 0.030 (3) | −0.001 (2) | 0.008 (2) | 0.001 (2) |
C1 | 0.038 (4) | 0.031 (3) | 0.026 (3) | −0.006 (3) | 0.009 (3) | −0.004 (2) |
C2 | 0.036 (4) | 0.034 (3) | 0.031 (3) | −0.001 (3) | 0.008 (3) | 0.003 (3) |
C3 | 0.050 (4) | 0.034 (3) | 0.031 (3) | 0.001 (3) | 0.012 (3) | 0.002 (3) |
C4 | 0.042 (4) | 0.031 (3) | 0.024 (3) | 0.002 (3) | 0.008 (3) | 0.000 (2) |
C5 | 0.046 (4) | 0.035 (3) | 0.027 (3) | 0.007 (3) | 0.011 (3) | 0.001 (3) |
C6 | 0.050 (5) | 0.043 (4) | 0.035 (3) | −0.003 (3) | 0.025 (3) | −0.002 (3) |
C7 | 0.043 (5) | 0.056 (4) | 0.030 (3) | −0.002 (3) | 0.015 (3) | 0.002 (3) |
C8 | 0.038 (4) | 0.049 (4) | 0.039 (4) | −0.002 (3) | 0.015 (3) | 0.001 (3) |
C9 | 0.041 (4) | 0.049 (4) | 0.033 (3) | −0.008 (3) | 0.016 (3) | −0.005 (3) |
C10 | 0.051 (4) | 0.031 (3) | 0.042 (4) | −0.005 (3) | 0.014 (3) | 0.010 (3) |
C11 | 0.040 (4) | 0.035 (3) | 0.038 (3) | −0.005 (3) | 0.010 (3) | −0.000 (3) |
C12 | 0.051 (4) | 0.034 (3) | 0.027 (3) | 0.004 (3) | 0.009 (3) | −0.003 (3) |
C13 | 0.032 (4) | 0.044 (4) | 0.035 (3) | 0.002 (3) | 0.011 (3) | −0.003 (3) |
C14 | 0.044 (4) | 0.033 (3) | 0.027 (3) | 0.001 (3) | 0.010 (3) | −0.002 (3) |
C15 | 0.043 (4) | 0.035 (3) | 0.031 (3) | 0.003 (3) | 0.019 (3) | 0.005 (3) |
C16 | 0.048 (4) | 0.038 (4) | 0.035 (3) | 0.001 (3) | 0.020 (3) | −0.003 (3) |
C17 | 0.066 (5) | 0.042 (4) | 0.044 (4) | 0.004 (3) | 0.023 (3) | −0.008 (3) |
C18 | 0.045 (4) | 0.045 (4) | 0.034 (3) | 0.003 (3) | 0.011 (3) | 0.000 (3) |
C19 | 0.057 (5) | 0.040 (4) | 0.033 (3) | −0.017 (3) | 0.023 (3) | −0.003 (3) |
C20 | 0.045 (4) | 0.058 (4) | 0.030 (3) | −0.007 (3) | 0.010 (3) | −0.009 (3) |
C21 | 0.050 (4) | 0.053 (4) | 0.029 (3) | 0.001 (4) | 0.008 (3) | 0.005 (3) |
C22 | 0.040 (4) | 0.043 (4) | 0.035 (3) | −0.002 (3) | 0.014 (3) | 0.001 (3) |
C23 | 0.069 (5) | 0.059 (5) | 0.040 (4) | 0.018 (4) | 0.017 (4) | 0.015 (3) |
Cl1—C23 | 1.758 (8) | C13—C16 | 1.511 (8) |
Cl2—C23 | 1.738 (7) | C14—C13 | 1.350 (8) |
Cl3—C23 | 1.767 (6) | C14—C15 | 1.434 (8) |
N1—C12 | 1.381 (7) | C14—C19 | 1.505 (9) |
N1—C15 | 1.377 (8) | C15—C22 | 1.385 (8) |
N1—H1 | 0.9500 | C16—C13 | 1.511 (8) |
N2—C2 | 1.375 (7) | C16—C17 | 1.551 (9) |
N2—C5 | 1.385 (9) | C16—C20 | 1.555 (8) |
C1—C2 | 1.401 (9) | C16—H12 | 0.9500 |
C1—C12 | 1.367 (9) | C17—C18 | 1.519 (9) |
C1—H2 | 0.9500 | C17—H15 | 0.9500 |
C2—C3 | 1.446 (9) | C17—H16 | 0.9500 |
C3—C4 | 1.370 (9) | C18—C19 | 1.543 (8) |
C3—C6 | 1.493 (8) | C18—H13 | 0.9500 |
C4—C5 | 1.446 (8) | C18—H14 | 0.9500 |
C4—C9 | 1.495 (9) | C19—C21 | 1.534 (7) |
C5—C22i | 1.404 (8) | C19—H11 | 0.9500 |
C6—C7 | 1.583 (8) | C20—C21 | 1.356 (9) |
C6—C10 | 1.513 (8) | C20—H18 | 0.9500 |
C6—H3 | 0.9500 | C21—H17 | 0.9500 |
C7—C8 | 1.525 (9) | C22—C5i | 1.404 (8) |
C7—H5 | 0.9500 | C22—H19 | 0.9300 |
C7—H6 | 0.9500 | C23—H20 | 0.9500 |
C8—C9 | 1.568 (7) | H4—C9 | 0.9500 |
C8—H7 | 0.9500 | H6—C7 | 0.9500 |
C8—H8 | 0.9500 | H7—C8 | 0.9500 |
C9—C11 | 1.496 (8) | H9—C10 | 0.9500 |
C9—H4 | 0.9500 | H10—C11 | 0.9500 |
C10—C6 | 1.513 (8) | H11—C19 | 0.9500 |
C10—C11 | 1.339 (9) | H12—C16 | 0.9500 |
C10—H9 | 0.9500 | H13—C18 | 0.9500 |
C11—C10 | 1.339 (9) | H14—C18 | 0.9500 |
C11—H10 | 0.9500 | H15—C17 | 0.9500 |
C12—C13 | 1.443 (9) | H16—C17 | 0.9500 |
C13—C12 | 1.443 (9) | H18—C20 | 0.9500 |
C13—C14 | 1.350 (8) | H20—C23 | 0.9500 |
Cl1—C23—H20 | 109.1680 | H7—C8—C9 | 109.5271 |
Cl2—C23—H20 | 109.1675 | H8—C8—C9 | 109.5272 |
Cl3—C23—H20 | 109.1675 | H8—C8—H7 | 109.4607 |
N1—C12—C1 | 126.5 (6) | C9—C11—C10 | 114.3 (6) |
N1—C12—C13 | 104.7 (5) | H4—C9—C11 | 112.6158 |
C15—N1—C12 | 111.8 (5) | C9—C11—H10 | 122.8553 |
H1—N1—C12 | 124.1125 | H9—C10—C11 | 122.4574 |
N1—C15—C14 | 105.6 (5) | C10—C11—H10 | 122.8555 |
N1—C15—C22 | 125.2 (6) | C12—C13—C14 | 109.3 (5) |
H1—N1—C15 | 124.1134 | C12—C13—C16 | 135.8 (6) |
N2—C2—C1 | 124.4 (5) | C13—C14—C15 | 108.6 (6) |
N2—C2—C3 | 110.4 (5) | C16—C13—C14 | 114.9 (6) |
C5—N2—C2 | 105.3 (5) | C13—C14—C19 | 115.6 (5) |
N2—C5—C4 | 111.1 (5) | C13—C16—C17 | 104.6 (4) |
N2—C5—C22i | 124.5 (5) | C13—C16—C20 | 105.1 (5) |
C12—C1—C2 | 127.4 (5) | C13—C16—H12 | 113.9563 |
C1—C2—C3 | 125.2 (5) | C14—C15—C22 | 129.2 (6) |
H2—C1—C2 | 116.3225 | C19—C14—C15 | 135.7 (5) |
C1—C12—C13 | 128.8 (5) | C14—C19—C21 | 105.9 (5) |
H2—C1—C12 | 116.3218 | C14—C19—C18 | 105.5 (5) |
C2—C3—C4 | 107.3 (5) | C14—C19—H11 | 113.3321 |
C2—C3—C6 | 138.4 (6) | C15—C22—H19 | 115.5218 |
C3—C4—C5 | 105.8 (6) | C15—C22—C5i | 128.9 (6) |
C6—C3—C4 | 114.1 (6) | C20—C16—C17 | 104.1 (5) |
C3—C4—C9 | 114.4 (5) | H12—C16—C17 | 113.9566 |
C3—C6—C7 | 105.1 (5) | C16—C17—H16 | 109.0174 |
C3—C6—C10 | 108.0 (4) | C16—C17—C18 | 111.3 (5) |
C3—C6—H3 | 113.3666 | C16—C17—H15 | 109.0170 |
C4—C5—C22i | 124.4 (6) | C16—C20—C21 | 115.1 (5) |
C9—C4—C5 | 139.5 (6) | H12—C16—C20 | 113.9565 |
C4—C9—C11 | 107.2 (5) | C16—C20—H18 | 122.4532 |
C4—C9—C8 | 105.8 (5) | C17—C18—C19 | 111.0 (5) |
C4—C9—H4 | 112.6163 | H16—C17—C18 | 109.0171 |
C5—C22i—H19i | 115.5284 | C17—C18—H13 | 109.0910 |
C5—C22i—C15i | 128.9 (6) | H15—C17—C18 | 109.0168 |
C10—C6—C7 | 102.8 (5) | C17—C18—H14 | 109.0908 |
H3—C6—C7 | 113.3665 | H16—C17—H15 | 109.4604 |
C6—C7—H6 | 109.2220 | C18—C19—C21 | 104.6 (5) |
C6—C7—C8 | 110.5 (4) | C18—C19—H11 | 113.3326 |
C6—C7—H5 | 109.2222 | H13—C18—C19 | 109.0905 |
C6—C10—C11 | 115.1 (5) | H14—C18—C19 | 109.0911 |
H3—C6—C10 | 113.3670 | H14—C18—H13 | 109.4601 |
C6—C10—H9 | 122.4567 | C19—C21—C20 | 113.9 (5) |
C7—C8—C9 | 109.3 (5) | H11—C19—C21 | 113.3321 |
H6—C7—C8 | 109.2223 | C19—C21—H17 | 123.0720 |
C7—C8—H7 | 109.5267 | H18—C20—C21 | 122.4533 |
H5—C7—C8 | 109.2222 | C20—C21—H17 | 123.0726 |
C7—C8—H8 | 109.5265 | H19—C22—C5i | 115.5284 |
H6—C7—H5 | 109.4599 | C22—C5i—N2i | 124.5 (5) |
C8—C9—C11 | 105.4 (4) | C22—C5i—C4i | 124.4 (6) |
C8—C9—H4 | 112.6162 |
Symmetry code: (i) −x, −y, −z. |