Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270100000032/fr1230sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270100000032/fr1230Isup2.hkl |
CCDC reference: 144634
The title compound was synthesized by the reaction of methyl 2-chloro-1-(p-chlorophenylmethyl)-1H-benzimidazole-5-carboxylate with N-methylpiperazine, and its structure was assigned by NMR, mass spectra and elemental analysis results (Göker et al., 1998).
H atoms were placed geometrically 0.95 Å from their parent atoms. For all H atoms a riding model was used with Uiso(H) = 1.3Ueq(C). Refinement with lower σ(I) cutoffs led to no significant changes in the results. Hydrogen bonds were calculated with PARST (Nardelli, 1995).
Data collection: CAD-4 EXPRESS (Enraf-Nonius, 1990); cell refinement: CAD-4 EXPRESS; data reduction: MolEN (Fair, 1990); program(s) used to solve structure: MolEN; program(s) used to refine structure: MolEN; molecular graphics: MolEN.
Fig. 1. ORTEP (Johnson, 1965) drawing of the title compound showing the atom-numbering scheme. The displacement ellipsoids are drawn at the 50% probability level. |
C21H23ClN4O2·0.5H2O | V = 2092.3 (3) Å3 |
Mr = 407.90 | Z = 4 |
Triclinic, P1 | Dx = 1.295 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71069 Å |
a = 11.227 (1) Å | Cell parameters from 25 reflections |
b = 13.443 (1) Å | θ = 11–18° |
c = 15.835 (2) Å | µ = 0.21 mm−1 |
α = 68.06 (1)° | T = 295 K |
β = 72.55 (1)° | Prismatic, yellow |
γ = 76.30 (1)° | 0.40 × 0.40 × 0.40 mm |
Enraf-Nonius CAD-4 diffractometer | Rint = 0.015 |
ω/2θ scans | θmax = 25.7°, θmin = 2.4° |
Absorption correction: empirical (using intensity measurements) ψ scans (North et al., 1968) | h = −13→0 |
Tmin = 0.853, Tmax = 0.922 | k = −16→15 |
8182 measured reflections | l = −19→18 |
7754 independent reflections | 3 standard reflections every 120 min |
5364 reflections with I > 3σ(I) | intensity decay: 3.3% |
Refinement on F | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.053 | w = 1/[σF2 + (0.02*F)2 + 1] |
wR(F2) = 0.068 | (Δ/σ)max = 0.010 |
S = 1.24 | Δρmax = 0.35 e Å−3 |
5364 reflections | Δρmin = −0.10 e Å−3 |
514 parameters |
C21H23ClN4O2·0.5H2O | γ = 76.30 (1)° |
Mr = 407.90 | V = 2092.3 (3) Å3 |
Triclinic, P1 | Z = 4 |
a = 11.227 (1) Å | Mo Kα radiation |
b = 13.443 (1) Å | µ = 0.21 mm−1 |
c = 15.835 (2) Å | T = 295 K |
α = 68.06 (1)° | 0.40 × 0.40 × 0.40 mm |
β = 72.55 (1)° |
Enraf-Nonius CAD-4 diffractometer | 5364 reflections with I > 3σ(I) |
Absorption correction: empirical (using intensity measurements) ψ scans (North et al., 1968) | Rint = 0.015 |
Tmin = 0.853, Tmax = 0.922 | 3 standard reflections every 120 min |
8182 measured reflections | intensity decay: 3.3% |
7754 independent reflections |
R[F2 > 2σ(F2)] = 0.053 | 514 parameters |
wR(F2) = 0.068 | H-atom parameters constrained |
S = 1.24 | Δρmax = 0.35 e Å−3 |
5364 reflections | Δρmin = −0.10 e Å−3 |
x | y | z | Uiso*/Ueq | ||
CL1 | 0.4418 (1) | 0.4189 (1) | 0.2599 (1) | 0.0828 (5) | |
O1 | 1.1370 (3) | 0.8364 (2) | 0.0784 (2) | 0.0915 (10) | |
O2 | 0.9395 (3) | 0.8999 (2) | 0.1381 (2) | 0.0836 (11) | |
O3 | 0.7534 (3) | 0.4752 (3) | 0.4440 (2) | 0.1045 (17) | |
N1 | 0.8342 (2) | 0.6966 (2) | −0.1244 (2) | 0.0492 (8) | |
N2 | 0.9506 (3) | 0.5744 (2) | −0.2076 (2) | 0.0518 (8) | |
N3 | 1.0423 (3) | 0.6477 (2) | −0.1287 (2) | 0.0496 (8) | |
N4 | 1.0033 (3) | 0.4630 (2) | −0.3384 (2) | 0.0622 (10) | |
C2 | 0.9473 (3) | 0.6383 (3) | −0.1556 (2) | 0.0464 (10) | |
C4 | 1.0454 (3) | 0.7496 (2) | −0.0243 (2) | 0.0489 (10) | |
C5 | 0.9679 (3) | 0.8152 (2) | 0.0274 (2) | 0.0509 (10) | |
C6 | 0.8401 (3) | 0.8441 (3) | 0.0298 (2) | 0.0595 (12) | |
C7 | 0.7827 (3) | 0.8111 (3) | −0.0192 (2) | 0.0583 (15) | |
C8 | 0.8612 (3) | 0.7454 (2) | −0.0701 (2) | 0.0473 (11) | |
C9 | 0.9891 (3) | 0.7148 (3) | −0.0733 (2) | 0.0459 (11) | |
C10 | 0.7077 (3) | 0.6825 (3) | −0.1206 (2) | 0.0564 (13) | |
C11 | 0.6416 (3) | 0.6181 (2) | −0.0238 (2) | 0.0474 (8) | |
C12 | 0.7060 (3) | 0.5306 (3) | 0.0327 (2) | 0.0566 (14) | |
C13 | 0.6455 (3) | 0.4696 (3) | 0.1198 (2) | 0.0599 (15) | |
C14 | 0.5182 (3) | 0.4971 (3) | 0.1500 (2) | 0.0555 (14) | |
C15 | 0.4513 (3) | 0.5835 (3) | 0.0965 (3) | 0.0671 (16) | |
C16 | 0.5143 (3) | 0.6437 (3) | 0.0092 (2) | 0.0625 (15) | |
C20 | 1.0584 (4) | 0.4895 (3) | −0.2103 (2) | 0.0639 (15) | |
C21 | 1.0300 (4) | 0.4101 (3) | −0.2459 (2) | 0.0694 (16) | |
C22 | 0.8974 (4) | 0.5487 (3) | −0.3351 (2) | 0.0634 (15) | |
C23 | 0.9249 (4) | 0.6302 (3) | −0.3014 (2) | 0.0570 (13) | |
C24 | 0.9766 (5) | 0.3825 (3) | −0.3698 (3) | 0.0926 (18) | |
C51 | 1.0270 (4) | 0.8509 (3) | 0.0818 (2) | 0.0599 (15) | |
C52 | 0.9859 (4) | 0.9352 (3) | 0.1964 (2) | 0.0908 (18) | |
CL1' | 0.8824 (1) | 0.2067 (1) | 0.5581 (1) | 0.0930 (4) | |
O1' | 1.4372 (3) | 0.0199 (2) | 0.9094 (2) | 0.1030 (12) | |
O2' | 1.6230 (2) | 0.0186 (2) | 0.8093 (2) | 0.0770 (8) | |
N1' | 1.3717 (2) | −0.1916 (2) | 0.6321 (2) | 0.0492 (8) | |
N2' | 1.5017 (3) | −0.2213 (2) | 0.4894 (2) | 0.0488 (8) | |
N3' | 1.5713 (3) | −0.1520 (2) | 0.5822 (2) | 0.0482 (8) | |
N4' | 1.6005 (3) | −0.3254 (2) | 0.3492 (2) | 0.0575 (10) | |
C2' | 1.4857 (3) | −0.1893 (2) | 0.5658 (2) | 0.0455 (10) | |
C4' | 1.5541 (3) | −0.0795 (3) | 0.7117 (2) | 0.0497 (13) | |
C5' | 1.4721 (3) | −0.0621 (3) | 0.7925 (2) | 0.0517 (10) | |
C6' | 1.3514 (3) | −0.0921 (3) | 0.8249 (2) | 0.0573 (14) | |
C7' | 1.3077 (3) | −0.1373 (3) | 0.7776 (2) | 0.0522 (14) | |
C8' | 1.3884 (3) | −0.1523 (2) | 0.6963 (2) | 0.0458 (11) | |
C9' | 1.5109 (3) | −0.1258 (2) | 0.6638 (2) | 0.0447 (11) | |
C10' | 1.2494 (3) | −0.2049 (2) | 0.6274 (2) | 0.0542 (13) | |
C11' | 1.1583 (3) | −0.1008 (2) | 0.6130 (2) | 0.0444 (9) | |
C12' | 1.1975 (3) | −0.0038 (3) | 0.5503 (2) | 0.0532 (15) | |
C13' | 1.1135 (3) | 0.0897 (3) | 0.5339 (2) | 0.0596 (15) | |
C14' | 0.9884 (3) | 0.0878 (2) | 0.5793 (2) | 0.0584 (10) | |
C15' | 0.9471 (3) | −0.0066 (3) | 0.6428 (2) | 0.0623 (14) | |
C16' | 1.0327 (3) | −0.1003 (2) | 0.6599 (2) | 0.0519 (13) | |
C20' | 1.6186 (4) | −0.1953 (3) | 0.4178 (2) | 0.0598 (14) | |
C21' | 1.6153 (4) | −0.2136 (3) | 0.3302 (2) | 0.0667 (17) | |
C22' | 1.4819 (4) | −0.3480 (3) | 0.4192 (2) | 0.0602 (12) | |
C23' | 1.4871 (4) | −0.3350 (2) | 0.5088 (2) | 0.0535 (12) | |
C24' | 1.5985 (4) | −0.3423 (3) | 0.2633 (2) | 0.0828 (18) | |
C51' | 1.5069 (3) | −0.0051 (3) | 0.8449 (2) | 0.0635 (15) | |
C52' | 1.6588 (4) | 0.0838 (3) | 0.8517 (3) | 0.0936 (15) | |
H4 | 1.133 | 0.730 | −0.026 | 0.0646* | |
H6 | 0.790 | 0.888 | 0.066 | 0.0709* | |
H7 | 0.695 | 0.831 | −0.018 | 0.0722* | |
H12 | 0.795 | 0.513 | 0.011 | 0.0722* | |
H13 | 0.690 | 0.409 | 0.158 | 0.0773* | |
H15 | 0.363 | 0.601 | 0.119 | 0.0848* | |
H16 | 0.469 | 0.705 | −0.028 | 0.0773* | |
H101 | 0.714 | 0.645 | −0.163 | 0.0709* | |
H102 | 0.659 | 0.752 | −0.139 | 0.0709* | |
H201 | 1.073 | 0.454 | −0.149 | 0.0798* | |
H202 | 1.132 | 0.520 | −0.251 | 0.0798* | |
H211 | 1.100 | 0.355 | −0.249 | 0.0862* | |
H212 | 0.958 | 0.379 | −0.204 | 0.0861* | |
H221 | 0.824 | 0.519 | −0.294 | 0.0785* | |
H222 | 0.883 | 0.584 | −0.396 | 0.0785* | |
H231 | 0.997 | 0.662 | −0.343 | 0.0709* | |
H232 | 0.854 | 0.685 | −0.298 | 0.0709* | |
H521 | 0.916 | 0.967 | 0.234 | 0.1140* | |
H522 | 1.031 | 0.876 | 0.236 | 0.1140* | |
H523 | 1.040 | 0.988 | 0.158 | 0.1140* | |
H241 | 1.046 | 0.326 | −0.372 | 0.1165* | |
H242 | 0.904 | 0.353 | −0.327 | 0.1165* | |
H243 | 0.960 | 0.417 | −0.430 | 0.1165* | |
H31 | 0.672 | 0.492 | 0.480 | 0.1330* | |
H32 | 0.806 | 0.524 | 0.438 | 0.1330* | |
H4' | 1.636 | −0.059 | 0.690 | 0.0620* | |
H6' | 1.299 | −0.082 | 0.881 | 0.0697* | |
H7' | 1.225 | −0.158 | 0.799 | 0.0671* | |
H12' | 1.284 | −0.003 | 0.519 | 0.0697* | |
H13' | 1.141 | 0.156 | 0.491 | 0.0773* | |
H15' | 0.860 | −0.007 | 0.674 | 0.0747* | |
H16' | 1.006 | −0.165 | 0.705 | 0.0697* | |
H101' | 1.214 | −0.256 | 0.684 | 0.0684* | |
H102' | 1.261 | −0.231 | 0.577 | 0.0684* | |
H201' | 1.688 | −0.242 | 0.440 | 0.0773* | |
H202' | 1.628 | −0.122 | 0.405 | 0.0773* | |
H211' | 1.545 | −0.167 | 0.308 | 0.0887* | |
H212' | 1.691 | −0.197 | 0.284 | 0.0887* | |
H221' | 1.469 | −0.420 | 0.431 | 0.0735* | |
H222' | 1.414 | −0.298 | 0.396 | 0.0735* | |
H231' | 1.411 | −0.352 | 0.555 | 0.0684* | |
H232' | 1.557 | −0.383 | 0.530 | 0.0684* | |
H241' | 1.589 | −0.415 | 0.277 | 0.1013* | |
H242' | 1.530 | −0.296 | 0.239 | 0.1013* | |
H243' | 1.675 | −0.327 | 0.218 | 0.1013* | |
H521' | 1.743 | 0.098 | 0.822 | 0.1127* | |
H522' | 1.604 | 0.150 | 0.844 | 0.1127* | |
H523' | 1.652 | 0.045 | 0.917 | 0.1127* |
U11 | U22 | U33 | U12 | U13 | U23 | |
CL1 | 0.066 (1) | 0.100 (1) | 0.070 (1) | −0.022 (1) | −0.013 (1) | −0.002 (1) |
O1 | 0.071 (1) | 0.121 (2) | 0.100 (1) | −0.025 (1) | −0.019 (1) | −0.065 (1) |
O2 | 0.081 (2) | 0.095 (1) | 0.082 (1) | 0.000 (1) | −0.031 (1) | −0.058 (1) |
O3 | 0.069 (2) | 0.096 (2) | 0.112 (2) | −0.017 (2) | 0.010 (2) | −0.013 (2) |
N1 | 0.045 (1) | 0.054 (1) | 0.047 (1) | −0.004 (1) | −0.012 (1) | −0.023 (1) |
N2 | 0.054 (1) | 0.048 (1) | 0.050 (1) | 0.001 (1) | −0.017 (1) | −0.023 (1) |
N3 | 0.046 (1) | 0.052 (1) | 0.047 (1) | −0.003 (1) | −0.010 (1) | −0.023 (1) |
N4 | 0.064 (2) | 0.061 (1) | 0.066 (1) | −0.014 (1) | −0.009 (1) | −0.036 (1) |
C2 | 0.048 (2) | 0.046 (1) | 0.040 (1) | −0.003 (1) | −0.010 (1) | −0.016 (1) |
C4 | 0.048 (2) | 0.054 (1) | 0.045 (1) | −0.012 (1) | −0.010 (1) | −0.016 (1) |
C5 | 0.061 (2) | 0.049 (1) | 0.046 (1) | −0.013 (1) | −0.014 (1) | −0.016 (1) |
C6 | 0.061 (2) | 0.060 (2) | 0.054 (1) | −0.003 (1) | −0.011 (1) | −0.031 (1) |
C7 | 0.048 (2) | 0.061 (2) | 0.059 (2) | 0.002 (1) | −0.013 (1) | −0.030 (1) |
C8 | 0.051 (2) | 0.050 (1) | 0.041 (1) | −0.009 (1) | −0.010 (1) | −0.018 (1) |
C9 | 0.046 (2) | 0.048 (1) | 0.041 (1) | −0.009 (1) | −0.007 (1) | −0.015 (1) |
C10 | 0.046 (2) | 0.068 (2) | 0.053 (1) | −0.001 (1) | −0.021 (1) | −0.023 (1) |
C11 | 0.041 (1) | 0.051 (1) | 0.051 (1) | −0.002 (1) | −0.017 (1) | −0.024 (1) |
C12 | 0.040 (2) | 0.061 (2) | 0.061 (2) | −0.000 (1) | −0.014 (1) | −0.023 (1) |
C13 | 0.053 (2) | 0.056 (2) | 0.064 (2) | −0.000 (1) | −0.023 (1) | −0.016 (1) |
C14 | 0.052 (2) | 0.061 (2) | 0.056 (2) | −0.013 (1) | −0.017 (1) | −0.017 (1) |
C15 | 0.039 (2) | 0.080 (2) | 0.070 (2) | −0.004 (2) | −0.014 (1) | −0.018 (2) |
C20 | 0.065 (2) | 0.056 (2) | 0.068 (2) | −0.000 (2) | −0.021 (1) | −0.030 (1) |
C21 | 0.075 (2) | 0.053 (2) | 0.078 (2) | −0.005 (2) | −0.018 (2) | −0.032 (1) |
C22 | 0.061 (2) | 0.076 (2) | 0.057 (2) | −0.014 (2) | −0.011 (1) | −0.033 (1) |
C23 | 0.064 (2) | 0.057 (2) | 0.046 (1) | −0.005 (2) | −0.012 (1) | −0.022 (1) |
C24 | 0.110 (3) | 0.087 (2) | 0.095 (2) | −0.024 (2) | −0.019 (2) | −0.056 (1) |
C51 | 0.073 (2) | 0.059 (2) | 0.055 (2) | −0.019 (1) | −0.016 (1) | −0.021 (1) |
C52 | 0.111 (3) | 0.093 (2) | 0.081 (2) | −0.007 (2) | −0.037 (2) | −0.054 (1) |
C16 | 0.047 (2) | 0.062 (2) | 0.066 (2) | 0.006 (2) | −0.025 (1) | −0.014 (1) |
CL1' | 0.092 (1) | 0.074 (1) | 0.114 (1) | 0.023 (1) | −0.059 (1) | −0.055 (1) |
O1' | 0.082 (2) | 0.154 (2) | 0.086 (1) | −0.022 (1) | −0.012 (1) | −0.079 (1) |
O2' | 0.068 (1) | 0.098 (1) | 0.078 (1) | −0.021 (1) | −0.019 (1) | −0.046 (1) |
N1' | 0.042 (1) | 0.050 (1) | 0.052 (1) | −0.007 (1) | −0.010 (1) | −0.023 (1) |
N2' | 0.055 (1) | 0.041 (1) | 0.048 (1) | −0.010 (1) | −0.005 (1) | −0.019 (1) |
N3' | 0.046 (1) | 0.047 (1) | 0.050 (1) | −0.012 (1) | −0.005 (1) | −0.018 (1) |
N4' | 0.067 (2) | 0.051 (1) | 0.050 (1) | −0.005 (1) | −0.010 (1) | −0.024 (1) |
C2' | 0.047 (2) | 0.039 (1) | 0.048 (1) | −0.007 (1) | −0.010 (1) | −0.015 (1) |
C4' | 0.048 (2) | 0.048 (1) | 0.055 (2) | −0.010 (1) | −0.018 (1) | −0.014 (1) |
C5' | 0.059 (2) | 0.050 (1) | 0.046 (1) | −0.003 (1) | −0.022 (1) | −0.016 (1) |
C6' | 0.051 (2) | 0.066 (2) | 0.048 (1) | −0.002 (2) | −0.011 (1) | −0.024 (1) |
C7' | 0.045 (2) | 0.066 (2) | 0.051 (2) | −0.010 (1) | −0.007 (1) | −0.022 (1) |
C8' | 0.042 (1) | 0.043 (1) | 0.049 (1) | −0.004 (1) | −0.012 (1) | −0.016 (1) |
C9' | 0.045 (2) | 0.041 (1) | 0.045 (1) | −0.006 (1) | −0.012 (1) | −0.012 (1) |
C10' | 0.047 (2) | 0.054 (2) | 0.065 (2) | −0.012 (1) | −0.013 (1) | −0.026 (1) |
C11' | 0.042 (1) | 0.050 (1) | 0.047 (1) | −0.011 (1) | −0.012 (1) | −0.023 (1) |
C12' | 0.044 (2) | 0.060 (2) | 0.052 (2) | −0.012 (1) | −0.010 (1) | −0.013 (1) |
C13' | 0.070 (2) | 0.053 (2) | 0.059 (2) | −0.012 (1) | −0.025 (1) | −0.012 (1) |
C14' | 0.061 (2) | 0.056 (1) | 0.065 (1) | 0.002 (1) | −0.033 (1) | −0.033 (1) |
C15' | 0.039 (2) | 0.075 (2) | 0.076 (2) | −0.004 (1) | −0.015 (1) | −0.046 (1) |
C16' | 0.050 (2) | 0.056 (1) | 0.056 (2) | −0.021 (1) | −0.006 (1) | −0.023 (1) |
C20' | 0.068 (2) | 0.054 (2) | 0.056 (2) | −0.019 (1) | −0.001 (2) | −0.022 (1) |
C21' | 0.088 (3) | 0.060 (2) | 0.048 (2) | −0.019 (2) | −0.001 (2) | −0.020 (1) |
C22' | 0.065 (2) | 0.049 (1) | 0.067 (2) | −0.007 (1) | −0.015 (1) | −0.029 (1) |
C23' | 0.063 (2) | 0.041 (1) | 0.053 (2) | −0.011 (1) | −0.006 (1) | −0.018 (1) |
C24' | 0.100 (3) | 0.084 (2) | 0.064 (2) | −0.009 (2) | −0.018 (2) | −0.039 (1) |
C51' | 0.055 (2) | 0.074 (2) | 0.058 (2) | −0.003 (2) | −0.022 (1) | −0.022 (1) |
C52' | 0.099 (2) | 0.105 (2) | 0.103 (2) | −0.030 (2) | −0.040 (2) | −0.048 (2) |
CL1—C14 | 1.744 (3) | C16—H16 | 0.950 |
O1—C51 | 1.188 (5) | CL1'—C14' | 1.738 (3) |
O2—C51 | 1.343 (4) | O1'—C51' | 1.192 (5) |
O2—C52 | 1.440 (7) | O2'—C51' | 1.317 (5) |
O3—H31 | 0.950 | O2'—C52' | 1.463 (7) |
O3—H32 | 0.950 | N1'—C2' | 1.390 (4) |
N1—C2 | 1.382 (4) | N1'—C8' | 1.383 (5) |
N1—C8 | 1.389 (5) | N1'—C10' | 1.449 (5) |
N1—C10 | 1.455 (5) | N2'—C2' | 1.379 (5) |
N2—C2 | 1.382 (5) | N2'—C23' | 1.479 (5) |
N2—C20 | 1.455 (4) | N2'—C20' | 1.471 (4) |
N2—C23 | 1.476 (4) | N3'—C2' | 1.309 (5) |
N3—C2 | 1.304 (5) | N3'—C9' | 1.398 (4) |
N3—C9 | 1.403 (5) | N4'—C22' | 1.467 (4) |
N4—C21 | 1.461 (5) | N4'—C21' | 1.458 (5) |
N4—C22 | 1.449 (4) | N4'—C24' | 1.468 (6) |
N4—C24 | 1.466 (7) | C4'—C5' | 1.400 (5) |
C4—C5 | 1.397 (5) | C4'—C9' | 1.383 (6) |
C4—C9 | 1.385 (6) | C4'—H4' | 0.950 |
C4—H4 | 0.950 | C5'—C6' | 1.393 (5) |
C5—C6 | 1.385 (5) | C5'—C51' | 1.496 (7) |
C5—C51 | 1.488 (7) | C6'—C7' | 1.369 (7) |
C6—C7 | 1.380 (7) | C6'—H6' | 0.950 |
C6—H6 | 0.950 | C7'—C8' | 1.387 (5) |
C7—C8 | 1.395 (5) | C7'—H7' | 0.950 |
C7—H7 | 0.950 | C8'—C9' | 1.396 (5) |
C8—C9 | 1.385 (5) | C10'—C11' | 1.509 (4) |
C10—C11 | 1.512 (4) | C10'—H101' | 0.950 |
C10—H101 | 0.950 | C10'—H102' | 0.950 |
C10—H102 | 0.950 | C11'—C16' | 1.382 (4) |
C11—C12 | 1.382 (4) | C11'—C12' | 1.386 (4) |
C11—C16 | 1.374 (4) | C16'—C15' | 1.380 (4) |
C12—C13 | 1.376 (4) | C16'—H16' | 0.950 |
C12—H12 | 0.950 | C15'—C14' | 1.373 (4) |
C13—C14 | 1.370 (5) | C15'—H15' | 0.950 |
C13—H13 | 0.950 | C14'—C13' | 1.372 (5) |
C14—C15 | 1.366 (5) | C12'—C13' | 1.369 (5) |
C15—C16 | 1.384 (5) | C13'—H13' | 0.950 |
C15—H15 | 0.950 | C12'—H12' | 0.950 |
C20—C21 | 1.508 (7) | C23'—C22' | 1.510 (6) |
C20—H201 | 0.950 | C23'—H231' | 0.950 |
C20—H202 | 0.950 | C23'—H232' | 0.950 |
C21—H211 | 0.950 | C22'—H221' | 0.950 |
C21—H212 | 0.950 | C22'—H222' | 0.950 |
C22—C23 | 1.507 (7) | C21'—C20' | 1.508 (6) |
C22—H221 | 0.950 | C21'—H211' | 0.950 |
C22—H222 | 0.950 | C21'—H212' | 0.950 |
C23—H231 | 0.950 | C20'—H201' | 0.950 |
C23—H232 | 0.950 | C20'—H202' | 0.950 |
C24—H241 | 0.950 | C24'—H241' | 0.950 |
C24—H242 | 0.950 | C24'—H242' | 0.950 |
C24—H243 | 0.950 | C24'—H243' | 0.950 |
C52—H521 | 0.950 | C52'—H521' | 0.950 |
C52—H522 | 0.950 | C52'—H522' | 0.950 |
C52—H523 | 0.950 | C52'—H523' | 0.950 |
C51—O2—C52 | 116.1 (3) | C51'—O2'—C52' | 115.0 (3) |
H31—O3—H32 | 109.5 | C2'—N1'—C8' | 105.6 (3) |
C2—N1—C8 | 105.3 (3) | C2'—N1'—C10' | 129.1 (3) |
C2—N1—C10 | 127.4 (3) | C8'—N1'—C10' | 123.7 (3) |
C8—N1—C10 | 124.4 (3) | C2'—N2'—C23' | 117.1 (2) |
C2—N2—C20 | 115.7 (3) | C2'—N2'—C20' | 114.1 (3) |
C2—N2—C23 | 117.2 (3) | C23'—N2'—C20' | 109.3 (3) |
C20—N2—C23 | 110.8 (3) | C2'—N3'—C9' | 104.5 (3) |
C2—N3—C9 | 104.4 (3) | C22'—N4'—C21' | 108.0 (3) |
C21—N4—C22 | 109.7 (3) | C22'—N4'—C24' | 110.1 (4) |
C21—N4—C24 | 109.3 (3) | C21'—N4'—C24' | 110.8 (3) |
C22—N4—C24 | 111.2 (4) | N1'—C2'—N2' | 121.2 (3) |
N1—C2—N2 | 119.6 (3) | N1'—C2'—N3' | 113.7 (3) |
N1—C2—N3 | 114.0 (3) | N2'—C2'—N3' | 125.1 (3) |
N2—C2—N3 | 126.3 (3) | C5'—C4'—C9' | 117.9 (3) |
C5—C4—C9 | 117.3 (3) | C5'—C4'—H4' | 121.3 |
C5—C4—H4 | 121.6 | C9'—C4'—H4' | 120.8 |
C9—C4—H4 | 121.2 | C4'—C5'—C6' | 121.2 (4) |
C4—C5—C6 | 121.4 (4) | C4'—C5'—C51' | 121.6 (3) |
C4—C5—C51 | 117.5 (3) | C6'—C5'—C51' | 117.1 (3) |
C6—C5—C51 | 121.1 (3) | C5'—C6'—C7' | 121.3 (3) |
C5—C6—C7 | 122.1 (4) | C5'—C6'—H6' | 119.5 |
C5—C6—H6 | 118.9 | C7'—C6'—H6' | 119.2 |
C7—C6—H6 | 119.0 | C6'—C7'—C8' | 117.2 (3) |
C6—C7—C8 | 115.8 (3) | C6'—C7'—H7' | 121.9 |
C6—C7—H7 | 122.4 | C8'—C7'—H7' | 120.8 |
C8—C7—H7 | 121.8 | N1'—C8'—C7' | 131.3 (3) |
N1—C8—C7 | 130.6 (3) | N1'—C8'—C9' | 106.0 (3) |
N1—C8—C9 | 106.2 (3) | C7'—C8'—C9' | 122.7 (4) |
C7—C8—C9 | 123.2 (4) | N3'—C9'—C4' | 130.2 (3) |
N3—C9—C4 | 129.7 (3) | N3'—C9'—C8' | 110.2 (4) |
N3—C9—C8 | 110.1 (4) | C4'—C9'—C8' | 119.7 (3) |
C4—C9—C8 | 120.2 (3) | N1'—C10'—C11' | 112.8 (3) |
N1—C10—C11 | 112.4 (3) | N1'—C10'—H101' | 108.5 |
N1—C10—H101 | 108.6 | N1'—C10'—H102' | 108.5 |
N1—C10—H102 | 108.8 | C11'—C10'—H101' | 108.6 |
C11—C10—H101 | 108.6 | C11'—C10'—H102' | 109.0 |
C11—C10—H102 | 109.0 | H101'—C10'—H102' | 109.5 |
H101—C10—H102 | 109.5 | C10'—C11'—C16' | 120.7 (3) |
C10—C11—C12 | 121.4 (3) | C10'—C11'—C12' | 121.1 (3) |
C10—C11—C16 | 120.4 (3) | C16'—C11'—C12' | 118.2 (3) |
C12—C11—C16 | 118.2 (3) | C11'—C16'—C15' | 121.1 (3) |
C11—C12—C13 | 121.6 (3) | C11'—C16'—H16' | 119.0 |
C11—C12—H12 | 118.9 | C15'—C16'—H16' | 119.9 |
C13—C12—H12 | 119.5 | C16'—C15'—C14' | 119.3 (3) |
C12—C13—C14 | 118.5 (3) | C16'—C15'—H15' | 120.6 |
C12—C13—H13 | 121.3 | C14'—C15'—H15' | 120.1 |
C14—C13—H13 | 120.2 | CL1'—C14'—C15' | 119.9 (2) |
CL1—C14—C13 | 118.3 (2) | CL1'—C14'—C13' | 119.6 (2) |
CL1—C14—C15 | 120.0 (3) | C15'—C14'—C13' | 120.5 (3) |
C13—C14—C15 | 121.7 (3) | C14'—C13'—C12' | 119.8 (3) |
C14—C15—C16 | 118.8 (3) | C14'—C13'—H13' | 119.9 |
C14—C15—H15 | 120.1 | C12'—C13'—H13' | 120.3 |
C16—C15—H15 | 121.1 | C11'—C12'—C13' | 121.1 (3) |
N2—C20—C21 | 108.6 (4) | C11'—C12'—H12' | 118.7 |
N2—C20—H201 | 109.4 | C13'—C12'—H12' | 120.3 |
N2—C20—H202 | 109.9 | N2'—C23'—C22' | 109.1 (2) |
C21—C20—H201 | 110.1 | N2'—C23'—H231' | 109.3 |
C21—C20—H202 | 109.4 | N2'—C23'—H232' | 110.1 |
H201—C20—H202 | 109.5 | C22'—C23'—H231' | 109.9 |
N4—C21—C20 | 111.5 (3) | C22'—C23'—H232' | 108.9 |
N4—C21—H211 | 109.3 | H231'—C23'—H232' | 109.5 |
N4—C21—H212 | 108.6 | N4'—C22'—C23' | 109.7 (4) |
C20—C21—H211 | 109.5 | N4'—C22'—H221' | 109.5 |
C20—C21—H212 | 108.4 | N4'—C22'—H222' | 109.5 |
H211—C21—H212 | 109.5 | C23'—C22'—H221' | 109.8 |
N4—C22—C23 | 110.8 (4) | C23'—C22'—H222' | 108.9 |
N4—C22—H221 | 109.3 | H221'—C22'—H222' | 109.5 |
N4—C22—H222 | 109.1 | N4'—C21'—C20' | 111.4 (3) |
C23—C22—H221 | 109.3 | N4'—C21'—H211' | 108.9 |
C23—C22—H222 | 108.9 | N4'—C21'—H212' | 109.2 |
H221—C22—H222 | 109.5 | C20'—C21'—H211' | 108.0 |
N2—C23—C22 | 108.9 (3) | C20'—C21'—H212' | 109.8 |
N2—C23—H231 | 109.4 | H211'—C21'—H212' | 109.5 |
N2—C23—H232 | 109.6 | N2'—C20'—C21' | 109.8 (4) |
C22—C23—H231 | 109.5 | N2'—C20'—H201' | 109.1 |
C22—C23—H232 | 110.0 | N2'—C20'—H202' | 109.8 |
H231—C23—H232 | 109.5 | C21'—C20'—H201' | 108.1 |
N4—C24—H241 | 111.3 | C21'—C20'—H202' | 110.6 |
N4—C24—H242 | 108.4 | H201'—C20'—H202' | 109.5 |
N4—C24—H243 | 108.7 | N4'—C24'—H241' | 109.8 |
H241—C24—H242 | 109.5 | N4'—C24'—H242' | 109.5 |
H241—C24—H243 | 109.5 | N4'—C24'—H243' | 109.1 |
H242—C24—H243 | 109.5 | H241'—C24'—H242' | 109.5 |
O1—C51—O2 | 123.4 (4) | H241'—C24'—H243' | 109.5 |
O1—C51—C5 | 125.4 (4) | H242'—C24'—H243' | 109.5 |
O2—C51—C5 | 111.2 (3) | O1'—C51'—O2' | 123.2 (5) |
O2—C52—H521 | 108.5 | O1'—C51'—C5' | 124.5 (4) |
O2—C52—H522 | 110.9 | O2'—C51'—C5' | 112.2 (3) |
O2—C52—H523 | 109.0 | O2'—C52'—H521' | 110.1 |
H521—C52—H522 | 109.5 | O2'—C52'—H522' | 109.4 |
H521—C52—H523 | 109.5 | O2'—C52'—H523' | 108.9 |
H522—C52—H523 | 109.5 | H521'—C52'—H522' | 109.5 |
C11—C16—C15 | 121.2 (3) | H521'—C52'—H523' | 109.5 |
C11—C16—H16 | 119.6 | H522'—C52'—H523' | 109.5 |
C15—C16—H16 | 119.2 | ||
C52—O2—C51—O1 | −0.1 (5) | C52'—O2'—C51'—O1' | −3.2 (5) |
C52—O2—C51—C5 | 178.2 (3) | C52'—O2'—C51'—C5' | 174.3 (3) |
C51—O2—C52—H521 | −178.80 | C51'—O2'—C52'—H521' | −179.9 |
C51—O2—C52—H522 | −58.44 | C51'—O2'—C52'—H522' | −59.6 |
C51—O2—C52—H523 | 62.11 | C51'—O2'—C52'—H523' | 60.1 |
C8—N1—C2—N2 | 176.2 (3) | C8'—N1'—C2'—N2' | −178.6 (3) |
C8—N1—C2—N3 | −1.7 (3) | C8'—N1'—C2'—N3' | −0.3 (4) |
C10—N1—C2—N2 | 15.1 (4) | C10'—N1'—C2'—N2' | −13.0 (5) |
C10—N1—C2—N3 | −162.7 (3) | C10'—N1'—C2'—N3' | 165.3 (3) |
C2—N1—C8—C7 | −178.1 (3) | C2'—N1'—C8'—C7' | −179.2 (4) |
C2—N1—C8—C9 | 0.9 (3) | C2'—N1'—C8'—C9' | 1.4 (3) |
C10—N1—C8—C7 | −16.3 (5) | C10'—N1'—C8'—C7' | 14.2 (6) |
C10—N1—C8—C9 | 162.7 (3) | C10'—N1'—C8'—C9' | −165.2 (3) |
C2—N1—C10—C11 | 99.5 (4) | C2'—N1'—C10'—C11' | −105.9 (4) |
C2—N1—C10—H101 | −20.70 | C2'—N1'—C10'—H101' | 133.9 |
C2—N1—C10—H102 | −139.72 | C2'—N1'—C10'—H102' | 15.03 |
C8—N1—C10—C11 | −58.2 (4) | C8'—N1'—C10'—C11' | 57.4 (4) |
C8—N1—C10—H101 | −178.39 | C8'—N1'—C10'—H101' | −62.9 |
C8—N1—C10—H102 | 62.59 | C8'—N1'—C10'—H102' | 178.3 |
C20—N2—C2—N1 | −159.8 (3) | C23'—N2'—C2'—N1' | −61.2 (4) |
C20—N2—C2—N3 | 17.7 (5) | C23'—N2'—C2'—N3' | 120.7 (4) |
C23—N2—C2—N1 | 66.6 (4) | C20'—N2'—C2'—N1' | 169.3 (3) |
C23—N2—C2—N3 | −115.9 (4) | C20'—N2'—C2'—N3' | −8.7 (5) |
C2—N2—C20—C21 | 164.6 (3) | C2'—N2'—C23'—C22' | 168.8 (3) |
C2—N2—C20—H201 | 44.37 | C2'—N2'—C23'—H231' | 48.5 |
C2—N2—C20—H202 | −75.90 | C2'—N2'—C23'—H232' | −71.9 |
C23—N2—C20—C21 | −58.96 (4) | C20'—N2'—C23'—C22' | −59.6 (4) |
C23—N2—C20—H201 | −179.19 | C20'—N2'—C23'—H231' | −179.8 |
C23—N2—C20—H202 | 60.53 | C20'—N2'—C23'—H232' | 59.8 |
C2—N2—C23—C22 | −164.6 (3) | C2'—N2'—C20'—C21' | −169.2 (3) |
C2—N2—C23—H231 | 75.68 | C2'—N2'—C20'—H201' | 72.6 |
C2—N2—C23—H232 | −44.40 | C2'—N2'—C20'—H202' | −47.4 |
C20—N2—C23—C22 | 59.7 (4) | C23'—N2'—C20'—C21' | 57.7 (4) |
C20—N2—C23—H231 | −59.95 | C23'—N2'—C20'—H201' | −60.6 |
C20—N2—C23—H232 | 179.97 | C23'—N2'—C20'—H202' | 179.5 |
C9—N3—C2—N1 | 1.6 (3) | C9'—N3'—C2'—N1' | −1.0 (4) |
C9—N3—C2—N2 | −176.0 (3) | C9'—N3'—C2'—N2' | 177.2 (3) |
C2—N3—C9—C4 | 178.0 (3) | C2'—N3'—C9'—C4' | −177.4 (3) |
C2—N3—C9—C8 | −1.0 (3) | C2'—N3'—C9'—C8' | 1.9 (3) |
C22—N4—C21—C20 | −58.2 (4) | C21'—N4'—C22'—C23' | −61.3 (4) |
C22—N4—C21—H211 | −179.4 | C21'—N4'—C22'—H221' | 178.1 |
C22—N4—C21—H212 | 61.3 | C21'—N4'—C22'—H222' | 58.1 |
C24—N4—C21—C20 | 179.9 (4) | C24'—N4'—C22'—C23' | 177.6 (3) |
C24—N4—C21—H211 | 58.6 | C24'—N4'—C22'—H221' | 57.1 |
C24—N4—C21—H212 | −60.8 | C24'—N4'—C22'—H222' | −62.9 |
C21—N4—C22—C23 | 58.1 (4) | C22'—N4'—C21'—C20' | 59.7 (4) |
C21—N4—C22—H221 | −62.4 | C22'—N4'—C21'—H211' | −59.2 |
C21—N4—C22—H222 | 177.9 | C22'—N4'—C21'—H212' | −178.7 |
C24—N4—C22—C23 | 179.1 (3) | C24'—N4'—C21'—C20' | −179.5 (4) |
C24—N4—C22—H221 | 58.6 | C24'—N4'—C21'—H211' | 61.6 |
C24—N4—C22—H222 | −61.1 | C24'—N4'—C21'—H212' | −58.0 |
C21—N4—C24—H241 | −58.6 | C22'—N4'—C24'—H241' | −60.8 |
C21—N4—C24—H242 | 61.8 | C22'—N4'—C24'—H242' | 59.5 |
C21—N4—C24—H243 | −179.3 | C22'—N4'—C24'—H243' | 179.3 |
C22—N4—C24—H241 | −179.8 | C21'—N4'—C24'—H241' | 179.8 |
C22—N4—C24—H242 | −59.4 | C21'—N4'—C24'—H242' | −60.0 |
C22—N4—C24—H243 | 59.5 | C21'—N4'—C24'—H243' | 59.8 |
C9—C4—C5—C6 | 0.1 (4) | C9'—C4'—C5'—C6' | 1.1 (5) |
C9—C4—C5—C51 | 178.7 (3) | C9'—C4'—C5'—C51' | −175.4 (3) |
H4—C4—C5—C6 | 179.9 | H4'—C4'—C5'—C6' | −179.7 |
H4—C4—C5—C51 | −1.4 | H4'—C4'—C5'—C51' | 3.8 |
C5—C4—C9—N3 | −178.7 (3) | C5'—C4'—C9'—N3' | −179.9 (3) |
C5—C4—C9—C8 | 0.3 (5) | C5'—C4'—C9'—C8' | 0.7 (5) |
H4—C4—C9—N3 | 1.5 | H4'—C4'—C9'—N3' | 0.8 |
H4—C4—C9—C8 | −179.6 | H4'—C4'—C9'—C8' | −178.5 |
C4—C5—C6—C7 | −0.7 (5) | C4'—C5'—C6'—C7' | −1.6 (5) |
C4—C5—C6—H6 | 179.1 | C4'—C5'—C6'—H6' | 177.7 |
C51—C5—C6—C7 | −179.3 (3) | C51'—C5'—C6'—C7' | 175.1 (3) |
C51—C5—C6—H6 | 0.5 | C51'—C5'—C6'—H6' | −5.7 |
C4—C5—C51—O1 | 7.1 (5) | C4'—C5'—C51'—O1' | 173.5 (4) |
C4—C5—C51—O2 | −171.2 (3) | C4'—C5'—C51'—O2' | −4.0 (5) |
C6—C5—C51—O1 | −174.3 (3) | C6'—C5'—C51'—O1' | −3.1 (6) |
C6—C5—C51—O2 | 7.4 (4) | C6'—C5'—C51'—O2' | 179.3 (3) |
C5—C6—C7—C8 | 0.9 (5) | C5'—C6'—C7'—C8' | 0.1 (5) |
C5—C6—C7—H7 | −179.6 | C5'—C6'—C7'—H7' | −179.5 |
H6—C6—C7—C8 | −178.9 | H6'—C6'—C7'—C8' | −179.1 |
H6—C6—C7—H7 | 0.6 | H6'—C6'—C7'—H7' | 1.2 |
C6—C7—C8—N1 | 178.2 (3) | C6'—C7'—C8'—N1' | −177.6 (3) |
C6—C7—C8—C9 | −0.6 (5) | C6'—C7'—C8'—C9' | 1.7 (5) |
H7—C7—C8—N1 | −1.2 | H7'—C7'—C8'—N1' | 2.1 |
H7—C7—C8—C9 | 180.0 | H7'—C7'—C8'—C9' | −178.6 |
N1—C8—C9—N3 | 0.1 (3) | N1'—C8'—C9'—N3' | −2.1 (4) |
N1—C8—C9—C4 | −179.1 (3) | N1'—C8'—C9'—C4' | 177.3 (3) |
C7—C8—C9—N3 | 179.1 (3) | C7'—C8'—C9'—N3' | 178.5 (3) |
C7—C8—C9—C4 | −0.0 (6) | C7'—C8'—C9'—C4' | −2.1 (5) |
N1—C10—C11—C12 | −38.6 (5) | N1'—C10'—C11'—C16' | −139.7 (3) |
N1—C10—C11—C16 | 143.2 (3) | N1'—C10'—C11'—C12' | 42.3 (4) |
H101—C10—C11—C12 | 81.6 | H101'—C10'—C11'—C16' | −19.4 |
H101—C10—C11—C16 | −96.6 | H101'—C10'—C11'—C12' | 162.5 |
H102—C10—C11—C12 | −159.2 | H102'—C10'—C11'—C16' | 99.8 |
H102—C10—C11—C16 | 22.6 | H102'—C10'—C11'—C12' | −78.3 |
C10—C11—C12—C13 | −178.0 (3) | C10'—C11'—C16'—C15' | −175.9 (3) |
C10—C11—C12—H12 | 3.5 | C10'—C11'—C16'—H16' | 5.3 |
C16—C11—C12—C13 | 0.3 (5) | C12'—C11'—C16'—C15' | 2.2 (5) |
C16—C11—C12—H12 | −178.3 | C12'—C11'—C16'—H16' | −176.6 |
C10—C11—C16—C15 | 177.9 (4) | C10'—C11'—C12'—C13' | 176.9 (3) |
C10—C11—C16—H16 | −3.6 | C10'—C11'—C12'—H12' | −3.2 |
C12—C11—C16—C15 | −0.4 (6) | C16'—C11'—C12'—C13' | −1.2 (5) |
C12—C11—C16—H16 | 178.1 | C16'—C11'—C12'—H12' | 178.7 |
C11—C12—C13—C14 | −0.2 (6) | C11'—C16'—C15'—C14' | −1.3 (5) |
C11—C12—C13—H13 | 179.1 | C11'—C16'—C15'—H15' | 178.3 |
H12—C12—C13—C14 | 178.7 | H16'—C16'—C15'—C14' | 177.5 |
H12—C12—C13—H13 | −2.3 | H16'—C16'—C15'—H15' | −2.9 |
C12—C13—C14—CL1 | 179.5 (3) | C16'—C15'—C14'—CL1' | −179.1 (3) |
C12—C13—C14—C15 | −0.6 (6) | C16'—C15'—C14'—C13' | −0.7 (5) |
H13—C13—C14—CL1 | 0.5 | H15'—C15'—C14'—CL1' | 1.3 |
H13—C13—C14—C15 | −179.6 | H15'—C15'—C14'—C13' | 179.8 |
CL1—C14—C15—C16 | −179.5 (3) | CL1'—C14'—C13'—C12' | −179.9 (3) |
CL1—C14—C15—H15 | −0.6 | CL1'—C14'—C13'—H13' | 0.1 |
C13—C14—C15—C16 | 0.5 (6) | C15'—C14'—C13'—C12' | 1.7 (5) |
C13—C14—C15—H15 | 179.5 | C15'—C14'—C13'—H13' | −178.4 |
C14—C15—C16—C11 | −0.0 (7) | C14'—C13'—C12'—C11' | −0.7 (5) |
C14—C15—C16—H16 | −178.5 | C14'—C13'—C12'—H12' | 179.4 |
H15—C15—C16—C11 | −178.9 | H13'—C13'—C12'—C11' | 179.3 |
H15—C15—C16—H16 | 2.6 | H13'—C13'—C12'—H12' | −0.6 |
N2—C20—C21—N4 | 58.2 (4) | N2'—C23'—C22'—N4' | 62.0 (4) |
N2—C20—C21—H211 | 179.4 | N2'—C23'—C22'—H221' | −177.6 |
N2—C20—C21—H212 | −61.3 | N2'—C23'—C22'—H222' | −57.8 |
H201—C20—C21—N4 | 178.0 | H231'—C23'—C22'—N4' | −178.1 |
H201—C20—C21—H211 | −60.8 | H231'—C23'—C22'—H221' | −57.7 |
H201—C20—C21—H212 | 58.5 | H231'—C23'—C22'—H222' | 62.1 |
H202—C20—C21—N4 | −61.6 | H232'—C23'—C22'—N4' | −58.2 |
H202—C20—C21—H211 | 59.6 | H232'—C23'—C22'—H221' | 62.3 |
H202—C20—C21—H212 | 178.9 | H232'—C23'—C22'—H222' | −177.9 |
N4—C22—C23—N2 | −58.8 (4) | N4'—C21'—C20'—N2' | −58.6 (4) |
N4—C22—C23—H231 | 60.9 | N4'—C21'—C20'—H201' | 60.3 |
N4—C22—C23—H232 | −178.8 | N4'—C21'—C20'—H202' | −180.0 |
H221—C22—C23—N2 | 61.7 | H211'—C21'—C20'—N2' | 60.9 |
H221—C22—C23—H231 | −178.6 | H211'—C21'—C20'—H201' | 179.8 |
H221—C22—C23—H232 | −58.3 | H211'—C21'—C20'—H202' | −60.5 |
H222—C22—C23—N2 | −178.7 | H212'—C21'—C20'—N2' | −179.8 |
H222—C22—C23—H231 | −59.0 | H212'—C21'—C20'—H201' | −60.9 |
H222—C22—C23—H232 | 61.3 | H212'—C21'—C20'—H202' | 58.9 |
Experimental details
Crystal data | |
Chemical formula | C21H23ClN4O2·0.5H2O |
Mr | 407.90 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 295 |
a, b, c (Å) | 11.227 (1), 13.443 (1), 15.835 (2) |
α, β, γ (°) | 68.06 (1), 72.55 (1), 76.30 (1) |
V (Å3) | 2092.3 (3) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.21 |
Crystal size (mm) | 0.40 × 0.40 × 0.40 |
Data collection | |
Diffractometer | Enraf-Nonius CAD-4 diffractometer |
Absorption correction | Empirical (using intensity measurements) ψ scans (North et al., 1968) |
Tmin, Tmax | 0.853, 0.922 |
No. of measured, independent and observed [I > 3σ(I)] reflections | 8182, 7754, 5364 |
Rint | 0.015 |
(sin θ/λ)max (Å−1) | 0.610 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.053, 0.068, 1.24 |
No. of reflections | 5364 |
No. of parameters | 514 |
No. of restraints | ? |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.35, −0.10 |
Computer programs: CAD-4 EXPRESS (Enraf-Nonius, 1990), CAD-4 EXPRESS, MolEN (Fair, 1990), MolEN.
CL1—C14 | 1.744 (3) | CL1'—C14' | 1.738 (3) |
O1—C51 | 1.188 (5) | O1'—C51' | 1.192 (5) |
O2—C51 | 1.343 (4) | O2'—C51' | 1.317 (5) |
N1—C2 | 1.382 (4) | N1'—C2' | 1.390 (4) |
N1—C10 | 1.455 (5) | N1'—C10' | 1.449 (5) |
N2—C2 | 1.382 (5) | N2'—C2' | 1.379 (5) |
N3—C2 | 1.304 (5) | N3'—C2' | 1.309 (5) |
N4—C24 | 1.466 (7) | N4'—C24' | 1.468 (6) |
C5—C51 | 1.488 (7) | C5'—C51' | 1.496 (7) |
C51—O2—C52 | 116.1 (3) | C51'—O2'—C52' | 115.0 (3) |
C20—N2—C23 | 110.8 (3) | C2'—N2'—C20' | 114.1 (3) |
C21—N4—C22 | 109.7 (3) | C22'—N4'—C21' | 108.0 (3) |
N1—C2—N3 | 114.0 (3) | N1'—C2'—N3' | 113.7 (3) |
O1—C51—O2 | 123.4 (4) | O1'—C51'—O2' | 123.2 (5) |
C20—N2—C23—C22 | 59.7 (4) | C23'—N2'—C20'—C21' | 57.7 (4) |
C22—N4—C21—C20 | −58.2 (4) | C21'—N4'—C22'—C23' | −61.3 (4) |
C4—C5—C51—O1 | 7.1 (5) | C4'—C5'—C51'—O2' | −4.0 (5) |
N1—C10—C11—C12 | −38.6 (5) | N1'—C10'—C11'—C16' | −139.7 (3) |
C12—C13—C14—CL1 | 179.5 (3) | C16'—C15'—C14'—CL1' | −179.1 (3) |
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The benzimidazole nucleus is an essential part of many medicinally useful drugs. For example, omeprazole and lansoprazole are useful drugs in the treatment of peptic ulcers (Nishina et al., 1996), pimobendan is a non-glucosidic cardiotonic drug (Güngör et al., 1992), emedastine difumarate (KG-2413) (Sakai et al., 1989) and astemizole (Hismanal) (Awouters et al., 1983) were discovered for the treatment of allergic diseases and enviroxime is an active drug against rhinoviruses (Victor et al., 1997).
The present compound is also a benzimidazole which was prepared for its antimicrobial activity (Göker et al., 1998). The structure of the title compound, (I), was assigned by NMR, mass spectra and elemental analysis (Göker et al., 1998). Considering the biological importance of the benzimidazole ring system including substances, we describe in this paper the structure of the title compound, (I). \sch
The benzimidazole ring systems of two molecules (I and II) are planar. The bond lengths N1—C2 [1.382 (4) and 1.390 (4) Å] are comparatively longer than the value reported for benzimidazole [1.346 (4) Å; Escande & Galigne, 1974]. The N1—C10 [1.455 (5) and 1.449 (5) Å] and N2—C2 [1.382 (5) and 1.379 (5) Å] bond lengths are normal for Csp3—N and Csp2—N bonds (Allen et al., 1987). The phenyl ring at C10 is also planar and makes an angle of 101.19 (8) for (I) and 79.42 (8)° for (II) with the plane through the complete benzimidazole ring system.
The Cl1 and Cl1' atoms lie almost in the phenyl ring planes with the distance deviations of 0.016 (1) and 0.002 (1) Å from the phenyl planes, respectively.
The C—Cl bond length [Cl1—C14 1.744 (3) for (I) and 1.738 (3) Å for (II)] is within the normal range. In 1-benzyl-2-(2,6-dichloroanilinemethyl)-1H-benzimidazole the C—Cl bond lengths are 1.739 (2) and 1.737 (2) Å (Kendi et al., 1998).
The piperazine ring adopts a perfect chair comformation in (I) and (II) (Velmurugan et al., 1994; Özbey et al., 1998). Best planes through the four non-N atoms make dihedral angles of 42.22 (13) in (I) and 32.81 (17) in (II) with the benzimidazole ring systems. The methyl group at N4 of the piperazine ring is in the equatorial position (Allinger et al., 1965).
The structure shows that the COOCH3 group at C5 and the benzimidazole ring are almost coplanar with torsion angle C4—C5—C51—O1 7.1 (5)° [173.5 (4) in (II)]. The intramolecular distance C10—N2 of 2.968 (4) Å [3.033 (4) in (II)] is suggestive of a possible C—H···N interaction. Atom C10 is rotated towards to the piperazine ring with the torsion angle C10—N1—C2—N3 of -162.67 (29)°, possibly to enable N2 to interact with the proton of the C10 to form an intramolecular hydrogen bond. This angle is 179.89 (37)° in 6-chloro-1-(phenylmethyl)-2-[N-(phenylmethyl)-N-(2,6-dichlorophenyl)] methyl-1H-benzimidazole (Tunçbilek et al., 1997) and -179.6 (2) in 1-benzyl-2-(2,6-dichloroanilinomethyl)-1H-benzimidazole (Kendi et al., 1998).
The molecules are linked by hydrogen bonds of the O—H···N type involving the O atom of the water molecule of crystallization. The O—N distances [2.873 (4) for (I) and 2.957 (4) Å for (II)] suggest that water acts as a hydrogen-bond donor to the piperazine ring. The H2O(O3) molecule forms hydrogen bonds to both molecules in the asymmetric unit.