Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807047046/sg2192sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807047046/sg2192Isup2.hkl |
CCDC reference: 667258
The title compound was prepared according to the literature method of Zhang et al. (2006). Single crystals suitable for X-ray diffraction were obtained by slow evaporation of an ethyl acetate solution at room temperature over a period of six days.
All H atoms were located in difference Fourier maps and constrained to ride on their parent atoms, with C—H distances in the range 0.93–0.98 Å, and with Uiso(H) = 1.2 Ueq(C) H atoms.
Recently we have reported the structure of 3-(benzotriazol-1-yl)-1-(4-chlorophenyl)-1-oxopropan-2-yl 2-chlorobenzoate (II) (Zhang et al., 2006). As part of our ongoing studies of searching for triazole derivatives with higher pharmacological activities, the title compound, (I), was synthesized and its structure is presented here.
All bond lengths and angles are within normal ranges (Allen et al., 1987) and are comparable with those in the related compound, (II). In the molecule of (I), the asymmetric unit contains two molecules, A and B. The benzotriazole system is essentially planar, with a dihedral of 0.70 (2) and 0.73 (2)/% between the triazole rings (N1—N3/C10/C11 and N1'-N3'/C10'/C11') and benzne rings (C10—C15 and C10'-C15') in A and B, respectively. In A, the mean plane of the benzotriazole group makes dihedral angles of 17.55 (2) and 17.02 (1)/% with the C1—C6 and C17—C22 benzene rings, respectively. The corresponding dihedral angles in B are 26.66 (1) and 11.21 (1)/%. The dihedral angles between the latter two benzene rings are 30.88 (2) and 32.44 (2)/% in A and B, respectively.
In the crystal structure, the intermolecular C9—H9A···N3', C9'-H31B···N3 and C4'-H26A···Cl1 hydrogen bonds link the molecules, forming infinite chains along the a axis. The packing is further stabilized by π-π interactions, with Cg1···Cg7 (x, 1/2 - y, -1/2 + z) and Cg2···Cg6 (-x, 1 - y, 2 - z) distances of 3.710 (1) and 3.661 (1) /%A, respectively (Cg1, Cg2, Cg6 and Cg7 are the centroids of the rings N1—N3/C10/C11, N1'-N3'/C10'/C11', C10'-C15' and C17—C22, respectively).
For related literature, see: Zhang et al. (2006); Allen et al. (1987).
Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL (Sheldrick, 1997b).
C22H14Cl2FN3O3 | F(000) = 1872 |
Mr = 458.26 | Dx = 1.476 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 11.9859 (7) Å | Cell parameters from 3056 reflections |
b = 25.1527 (16) Å | θ = 2.4–21.2° |
c = 13.8358 (9) Å | µ = 0.35 mm−1 |
β = 98.647 (1)° | T = 293 K |
V = 4123.8 (4) Å3 | Block, colourless |
Z = 8 | 0.34 × 0.30 × 0.14 mm |
Siemens SMART 1000 CCD area-detector diffractometer | 8111 independent reflections |
Radiation source: fine-focus sealed tube | 4644 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.039 |
Detector resolution: 8.33 pixels mm-1 | θmax = 26.0°, θmin = 1.6° |
ω scans | h = −14→8 |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | k = −31→31 |
Tmin = 0.889, Tmax = 0.952 | l = −16→17 |
23035 measured reflections |
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)] = 0.060 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.151 | H-atom parameters constrained |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0623P)2 + 0.2266P] where P = (Fo2 + 2Fc2)/3 |
8111 reflections | (Δ/σ)max = 0.001 |
559 parameters | Δρmax = 0.22 e Å−3 |
0 restraints | Δρmin = −0.17 e Å−3 |
C22H14Cl2FN3O3 | V = 4123.8 (4) Å3 |
Mr = 458.26 | Z = 8 |
Monoclinic, P21/c | Mo Kα radiation |
a = 11.9859 (7) Å | µ = 0.35 mm−1 |
b = 25.1527 (16) Å | T = 293 K |
c = 13.8358 (9) Å | 0.34 × 0.30 × 0.14 mm |
β = 98.647 (1)° |
Siemens SMART 1000 CCD area-detector diffractometer | 8111 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 4644 reflections with I > 2σ(I) |
Tmin = 0.889, Tmax = 0.952 | Rint = 0.039 |
23035 measured reflections |
R[F2 > 2σ(F2)] = 0.060 | 0 restraints |
wR(F2) = 0.151 | H-atom parameters constrained |
S = 1.03 | Δρmax = 0.22 e Å−3 |
8111 reflections | Δρmin = −0.17 e Å−3 |
559 parameters |
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 | ||
Cl1' | 0.34033 (7) | 0.37234 (3) | 0.57244 (7) | 0.0729 (3) | |
Cl1 | −0.84381 (7) | 0.32434 (3) | 0.90731 (7) | 0.0769 (3) | |
Cl2' | 0.03377 (9) | 0.22597 (3) | 0.62058 (7) | 0.0860 (3) | |
Cl2 | −0.54316 (9) | 0.47425 (3) | 0.86955 (8) | 0.0875 (3) | |
O2 | −0.63982 (17) | 0.22146 (7) | 0.75847 (14) | 0.0571 (6) | |
N1 | −0.5387 (2) | 0.15190 (9) | 0.61983 (17) | 0.0516 (6) | |
N2' | −0.0207 (2) | 0.59177 (10) | 0.86134 (19) | 0.0615 (7) | |
O2' | 0.13449 (18) | 0.47776 (7) | 0.71538 (16) | 0.0658 (6) | |
N1' | 0.0338 (2) | 0.54473 (9) | 0.85562 (17) | 0.0496 (6) | |
O3 | −0.7272 (2) | 0.22071 (8) | 0.89038 (16) | 0.0714 (7) | |
C18 | −0.7131 (2) | 0.33972 (11) | 0.8769 (2) | 0.0484 (7) | |
C17 | −0.6439 (3) | 0.30175 (11) | 0.8436 (2) | 0.0483 (7) | |
C16 | −0.6762 (3) | 0.24432 (11) | 0.8364 (2) | 0.0515 (8) | |
C19 | −0.6818 (3) | 0.39220 (11) | 0.8847 (2) | 0.0571 (8) | |
H19A | −0.7293 | 0.4172 | 0.9067 | 0.068* | |
N2 | −0.4831 (3) | 0.10495 (10) | 0.6184 (2) | 0.0675 (8) | |
N3' | −0.1209 (2) | 0.58228 (11) | 0.8810 (2) | 0.0672 (8) | |
C22 | −0.5418 (3) | 0.31834 (12) | 0.8189 (2) | 0.0627 (9) | |
H22A | −0.4944 | 0.2935 | 0.7962 | 0.075* | |
C8 | −0.6625 (3) | 0.16534 (10) | 0.7475 (2) | 0.0527 (8) | |
H8A | −0.7393 | 0.1580 | 0.7601 | 0.063* | |
O3' | 0.2331 (2) | 0.47809 (9) | 0.59088 (18) | 0.0876 (8) | |
C9 | −0.6533 (2) | 0.15132 (12) | 0.6422 (2) | 0.0579 (8) | |
H9A | −0.6850 | 0.1162 | 0.6282 | 0.069* | |
H9B | −0.6984 | 0.1763 | 0.5995 | 0.069* | |
C19' | 0.1745 (3) | 0.30608 (12) | 0.5972 (2) | 0.0557 (8) | |
H41A | 0.2215 | 0.2800 | 0.5778 | 0.067* | |
C11 | −0.3738 (3) | 0.16814 (14) | 0.5827 (2) | 0.0616 (9) | |
C8' | 0.1612 (3) | 0.53319 (11) | 0.7308 (2) | 0.0557 (8) | |
H30A | 0.2394 | 0.5395 | 0.7211 | 0.067* | |
C10' | −0.0345 (2) | 0.50342 (11) | 0.8726 (2) | 0.0476 (7) | |
C15 | −0.4905 (3) | 0.24709 (13) | 0.5867 (2) | 0.0660 (9) | |
H15A | −0.5580 | 0.2631 | 0.5960 | 0.079* | |
C9' | 0.1490 (2) | 0.54536 (11) | 0.8360 (2) | 0.0536 (8) | |
H31A | 0.1924 | 0.5195 | 0.8781 | 0.064* | |
H31B | 0.1811 | 0.5801 | 0.8528 | 0.064* | |
C10 | −0.4737 (2) | 0.19277 (11) | 0.5968 (2) | 0.0482 (7) | |
N3 | −0.3843 (3) | 0.11433 (12) | 0.5964 (2) | 0.0741 (8) | |
C18' | 0.2077 (2) | 0.35877 (12) | 0.6012 (2) | 0.0494 (7) | |
C15' | −0.0207 (3) | 0.44841 (12) | 0.8769 (2) | 0.0601 (8) | |
H37A | 0.0461 | 0.4322 | 0.8662 | 0.072* | |
C16' | 0.1755 (3) | 0.45477 (12) | 0.6397 (2) | 0.0600 (9) | |
C17' | 0.1394 (3) | 0.39824 (12) | 0.6302 (2) | 0.0540 (8) | |
C20' | 0.0719 (3) | 0.29273 (12) | 0.6219 (2) | 0.0615 (9) | |
C21' | −0.0002 (3) | 0.33062 (14) | 0.6491 (3) | 0.0756 (10) | |
H43A | −0.0704 | 0.3213 | 0.6646 | 0.091* | |
C22' | 0.0350 (3) | 0.38318 (13) | 0.6525 (2) | 0.0724 (10) | |
H44A | −0.0130 | 0.4092 | 0.6704 | 0.087* | |
C21 | −0.5089 (3) | 0.37078 (13) | 0.8271 (2) | 0.0675 (9) | |
H21A | −0.4397 | 0.3812 | 0.8107 | 0.081* | |
C20 | −0.5798 (3) | 0.40763 (12) | 0.8599 (2) | 0.0585 (9) | |
C1' | 0.2164 (3) | 0.64490 (13) | 0.6779 (2) | 0.0706 (10) | |
H23A | 0.2770 | 0.6217 | 0.6930 | 0.085* | |
C11' | −0.1338 (3) | 0.52797 (13) | 0.8890 (2) | 0.0548 (8) | |
C7' | 0.0830 (3) | 0.56708 (14) | 0.6600 (2) | 0.0637 (9) | |
C1 | −0.7148 (3) | 0.05963 (13) | 0.8374 (2) | 0.0688 (9) | |
H1A | −0.7747 | 0.0833 | 0.8235 | 0.083* | |
C6' | 0.1092 (3) | 0.62478 (13) | 0.6561 (2) | 0.0573 (8) | |
C12' | −0.2249 (3) | 0.49825 (16) | 0.9085 (2) | 0.0719 (10) | |
H34A | −0.2922 | 0.5143 | 0.9183 | 0.086* | |
C6 | −0.6064 (3) | 0.07765 (13) | 0.8378 (2) | 0.0598 (8) | |
F1' | 0.1635 (3) | 0.78465 (9) | 0.6575 (2) | 0.1505 (12) | |
C13' | −0.2117 (3) | 0.44440 (17) | 0.9129 (3) | 0.0781 (11) | |
H35A | −0.2715 | 0.4235 | 0.9263 | 0.094* | |
C7 | −0.5786 (3) | 0.13398 (12) | 0.8188 (2) | 0.0582 (8) | |
C14 | −0.4023 (4) | 0.27588 (15) | 0.5621 (3) | 0.0849 (12) | |
H14A | −0.4098 | 0.3125 | 0.5537 | 0.102* | |
O1 | −0.4902 (2) | 0.15392 (10) | 0.85322 (19) | 0.0873 (8) | |
C14' | −0.1108 (3) | 0.41961 (14) | 0.8979 (2) | 0.0760 (11) | |
H36A | −0.1052 | 0.3828 | 0.9022 | 0.091* | |
C5 | −0.5184 (4) | 0.04214 (17) | 0.8588 (3) | 0.0987 (14) | |
H5B | −0.4446 | 0.0539 | 0.8603 | 0.118* | |
O1' | −0.0013 (2) | 0.54804 (11) | 0.6142 (2) | 0.1042 (9) | |
F1 | −0.6685 (3) | −0.07828 (10) | 0.8933 (2) | 0.1785 (14) | |
C5' | 0.0202 (3) | 0.65950 (17) | 0.6320 (3) | 0.0869 (12) | |
H27A | −0.0525 | 0.6462 | 0.6157 | 0.104* | |
C12 | −0.2841 (3) | 0.19776 (18) | 0.5579 (3) | 0.0869 (12) | |
H12A | −0.2168 | 0.1819 | 0.5478 | 0.104* | |
C4' | 0.0373 (5) | 0.7126 (2) | 0.6317 (3) | 0.1026 (16) | |
H26A | −0.0228 | 0.7359 | 0.6154 | 0.123* | |
C2' | 0.2360 (4) | 0.69905 (14) | 0.6777 (3) | 0.0869 (12) | |
H24A | 0.3086 | 0.7128 | 0.6919 | 0.104* | |
C13 | −0.3001 (4) | 0.25110 (19) | 0.5493 (3) | 0.0924 (13) | |
H13A | −0.2412 | 0.2721 | 0.5343 | 0.111* | |
C3' | 0.1444 (5) | 0.73137 (14) | 0.6558 (3) | 0.0924 (14) | |
C4 | −0.5384 (5) | −0.0103 (2) | 0.8775 (4) | 0.125 (2) | |
H4A | −0.4791 | −0.0343 | 0.8915 | 0.150* | |
C2 | −0.7365 (4) | 0.00691 (15) | 0.8574 (3) | 0.0894 (12) | |
H2B | −0.8097 | −0.0051 | 0.8586 | 0.107* | |
C3 | −0.6469 (6) | −0.02618 (16) | 0.8751 (3) | 0.1099 (17) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1' | 0.0613 (6) | 0.0613 (5) | 0.1003 (7) | −0.0031 (4) | 0.0262 (5) | −0.0085 (5) |
Cl1 | 0.0613 (6) | 0.0558 (5) | 0.1190 (8) | −0.0036 (4) | 0.0309 (5) | −0.0132 (5) |
Cl2' | 0.1007 (8) | 0.0586 (5) | 0.1043 (8) | −0.0226 (5) | 0.0342 (6) | −0.0107 (5) |
Cl2 | 0.0940 (7) | 0.0515 (5) | 0.1151 (8) | −0.0223 (5) | 0.0093 (6) | −0.0061 (5) |
O2 | 0.0615 (14) | 0.0436 (11) | 0.0705 (14) | −0.0052 (10) | 0.0240 (11) | −0.0096 (10) |
N1 | 0.0485 (16) | 0.0438 (14) | 0.0627 (17) | 0.0056 (12) | 0.0092 (13) | −0.0101 (11) |
N2' | 0.0602 (19) | 0.0478 (15) | 0.0771 (19) | 0.0116 (13) | 0.0125 (15) | −0.0036 (13) |
O2' | 0.0745 (16) | 0.0463 (12) | 0.0844 (16) | −0.0044 (11) | 0.0371 (13) | −0.0144 (11) |
N1' | 0.0458 (16) | 0.0407 (13) | 0.0635 (16) | 0.0066 (12) | 0.0115 (12) | −0.0046 (11) |
O3 | 0.0970 (19) | 0.0486 (13) | 0.0766 (16) | −0.0012 (12) | 0.0394 (14) | 0.0061 (11) |
C18 | 0.0489 (18) | 0.0456 (16) | 0.0498 (18) | −0.0025 (14) | 0.0044 (14) | −0.0019 (13) |
C17 | 0.0533 (19) | 0.0433 (16) | 0.0473 (18) | 0.0017 (15) | 0.0045 (15) | 0.0012 (13) |
C16 | 0.055 (2) | 0.0447 (17) | 0.056 (2) | 0.0042 (15) | 0.0101 (16) | 0.0013 (15) |
C19 | 0.059 (2) | 0.0455 (18) | 0.066 (2) | 0.0005 (16) | 0.0071 (17) | −0.0089 (14) |
N2 | 0.070 (2) | 0.0490 (16) | 0.086 (2) | 0.0127 (14) | 0.0215 (16) | −0.0113 (14) |
N3' | 0.0570 (19) | 0.0638 (19) | 0.082 (2) | 0.0165 (15) | 0.0132 (15) | 0.0005 (14) |
C22 | 0.063 (2) | 0.057 (2) | 0.071 (2) | 0.0001 (17) | 0.0187 (18) | −0.0089 (16) |
C8 | 0.0483 (19) | 0.0407 (16) | 0.071 (2) | −0.0038 (14) | 0.0137 (16) | −0.0086 (14) |
O3' | 0.122 (2) | 0.0588 (15) | 0.0950 (19) | −0.0115 (15) | 0.0602 (18) | −0.0053 (13) |
C9 | 0.0440 (19) | 0.0563 (19) | 0.072 (2) | −0.0048 (15) | 0.0063 (16) | −0.0117 (16) |
C19' | 0.056 (2) | 0.0502 (18) | 0.062 (2) | 0.0015 (16) | 0.0133 (16) | −0.0095 (15) |
C11 | 0.053 (2) | 0.072 (2) | 0.062 (2) | 0.0070 (18) | 0.0151 (17) | −0.0054 (17) |
C8' | 0.051 (2) | 0.0437 (17) | 0.075 (2) | −0.0029 (14) | 0.0180 (17) | −0.0069 (15) |
C10' | 0.0419 (18) | 0.0481 (17) | 0.0527 (19) | 0.0002 (14) | 0.0068 (14) | −0.0047 (14) |
C15 | 0.062 (2) | 0.061 (2) | 0.075 (2) | 0.0047 (18) | 0.0107 (19) | 0.0041 (17) |
C9' | 0.0444 (19) | 0.0430 (16) | 0.073 (2) | −0.0008 (14) | 0.0070 (16) | −0.0054 (14) |
C10 | 0.0468 (19) | 0.0490 (17) | 0.0489 (18) | 0.0030 (15) | 0.0073 (14) | −0.0020 (14) |
N3 | 0.066 (2) | 0.067 (2) | 0.093 (2) | 0.0230 (16) | 0.0239 (17) | −0.0058 (16) |
C18' | 0.0493 (19) | 0.0549 (18) | 0.0448 (17) | 0.0015 (15) | 0.0093 (14) | −0.0021 (14) |
C15' | 0.063 (2) | 0.0461 (18) | 0.072 (2) | 0.0027 (16) | 0.0140 (17) | −0.0036 (15) |
C16' | 0.068 (2) | 0.0528 (19) | 0.063 (2) | 0.0029 (17) | 0.0217 (18) | −0.0043 (16) |
C17' | 0.060 (2) | 0.0523 (18) | 0.0528 (19) | −0.0006 (16) | 0.0170 (16) | −0.0047 (14) |
C20' | 0.072 (2) | 0.0539 (19) | 0.060 (2) | −0.0055 (18) | 0.0148 (18) | −0.0073 (15) |
C21' | 0.072 (3) | 0.073 (2) | 0.089 (3) | −0.018 (2) | 0.035 (2) | −0.018 (2) |
C22' | 0.072 (3) | 0.066 (2) | 0.086 (3) | −0.0002 (19) | 0.032 (2) | −0.0215 (18) |
C21 | 0.061 (2) | 0.065 (2) | 0.078 (2) | −0.0186 (18) | 0.0159 (19) | −0.0062 (18) |
C20 | 0.072 (2) | 0.0439 (17) | 0.058 (2) | −0.0110 (17) | 0.0012 (18) | −0.0030 (14) |
C1' | 0.069 (2) | 0.052 (2) | 0.091 (3) | 0.0116 (18) | 0.009 (2) | 0.0164 (18) |
C11' | 0.0436 (19) | 0.066 (2) | 0.054 (2) | 0.0038 (17) | 0.0053 (15) | 0.0008 (15) |
C7' | 0.055 (2) | 0.072 (2) | 0.064 (2) | 0.0011 (18) | 0.0082 (18) | −0.0093 (18) |
C1 | 0.079 (3) | 0.052 (2) | 0.073 (2) | 0.0033 (18) | 0.0007 (19) | 0.0020 (16) |
C6' | 0.059 (2) | 0.063 (2) | 0.0495 (19) | 0.0142 (17) | 0.0095 (16) | 0.0060 (15) |
C12' | 0.052 (2) | 0.090 (3) | 0.073 (2) | 0.002 (2) | 0.0082 (18) | 0.003 (2) |
C6 | 0.067 (2) | 0.058 (2) | 0.056 (2) | 0.0123 (18) | 0.0129 (17) | −0.0050 (15) |
F1' | 0.261 (4) | 0.0524 (14) | 0.151 (2) | 0.0348 (18) | 0.075 (2) | 0.0217 (14) |
C13' | 0.063 (3) | 0.098 (3) | 0.075 (3) | −0.022 (2) | 0.016 (2) | 0.007 (2) |
C7 | 0.057 (2) | 0.058 (2) | 0.062 (2) | 0.0043 (17) | 0.0129 (17) | −0.0143 (16) |
C14 | 0.101 (3) | 0.067 (2) | 0.092 (3) | −0.007 (2) | 0.029 (2) | 0.012 (2) |
O1 | 0.0586 (16) | 0.0885 (18) | 0.108 (2) | −0.0064 (14) | −0.0091 (14) | −0.0116 (15) |
C14' | 0.095 (3) | 0.058 (2) | 0.078 (3) | −0.017 (2) | 0.020 (2) | 0.0029 (18) |
C5 | 0.098 (3) | 0.088 (3) | 0.119 (4) | 0.041 (3) | 0.045 (3) | 0.026 (3) |
O1' | 0.083 (2) | 0.111 (2) | 0.109 (2) | −0.0135 (17) | −0.0187 (17) | −0.0123 (17) |
F1 | 0.280 (4) | 0.0628 (16) | 0.199 (3) | 0.014 (2) | 0.057 (3) | 0.0405 (18) |
C5' | 0.077 (3) | 0.101 (3) | 0.084 (3) | 0.036 (2) | 0.016 (2) | 0.025 (2) |
C12 | 0.065 (3) | 0.108 (3) | 0.095 (3) | 0.006 (2) | 0.034 (2) | −0.001 (2) |
C4' | 0.123 (4) | 0.088 (3) | 0.104 (3) | 0.059 (3) | 0.039 (3) | 0.033 (3) |
C2' | 0.105 (3) | 0.057 (2) | 0.096 (3) | −0.001 (2) | 0.008 (2) | 0.015 (2) |
C13 | 0.086 (3) | 0.109 (4) | 0.089 (3) | −0.032 (3) | 0.033 (2) | 0.004 (2) |
C3' | 0.164 (5) | 0.044 (2) | 0.077 (3) | 0.028 (3) | 0.041 (3) | 0.0142 (19) |
C4 | 0.144 (5) | 0.090 (4) | 0.152 (5) | 0.065 (4) | 0.062 (4) | 0.046 (3) |
C2 | 0.115 (3) | 0.063 (2) | 0.086 (3) | −0.014 (2) | 0.002 (3) | 0.005 (2) |
C3 | 0.180 (6) | 0.053 (3) | 0.102 (3) | 0.023 (3) | 0.039 (4) | 0.015 (2) |
Cl1'—C18' | 1.730 (3) | C18'—C17' | 1.384 (4) |
Cl1—C18 | 1.726 (3) | C15'—C14' | 1.368 (4) |
Cl2'—C20' | 1.740 (3) | C15'—H37A | 0.9300 |
Cl2—C20 | 1.732 (3) | C16'—C17' | 1.487 (4) |
O2—C16 | 1.351 (3) | C17'—C22' | 1.385 (4) |
O2—C8 | 1.441 (3) | C20'—C21' | 1.376 (4) |
N1—C10 | 1.357 (3) | C21'—C22' | 1.387 (4) |
N1—N2 | 1.358 (3) | C21'—H43A | 0.9300 |
N1—C9 | 1.453 (3) | C22'—H44A | 0.9300 |
N2'—N3' | 1.293 (3) | C21—C20 | 1.379 (4) |
N2'—N1' | 1.359 (3) | C21—H21A | 0.9300 |
O2'—C16' | 1.352 (3) | C1'—C6' | 1.371 (4) |
O2'—C8' | 1.439 (3) | C1'—C2' | 1.382 (4) |
N1'—C10' | 1.365 (3) | C1'—H23A | 0.9300 |
N1'—C9' | 1.447 (3) | C11'—C12' | 1.383 (4) |
O3—C16 | 1.192 (3) | C7'—O1' | 1.207 (4) |
C18—C19 | 1.372 (4) | C7'—C6' | 1.488 (4) |
C18—C17 | 1.389 (4) | C1—C6 | 1.375 (4) |
C17—C22 | 1.383 (4) | C1—C2 | 1.387 (4) |
C17—C16 | 1.495 (4) | C1—H1A | 0.9300 |
C19—C20 | 1.374 (4) | C6'—C5' | 1.380 (4) |
C19—H19A | 0.9300 | C12'—C13' | 1.364 (5) |
N2—N3 | 1.288 (4) | C12'—H34A | 0.9300 |
N3'—C11' | 1.381 (4) | C6—C5 | 1.379 (5) |
C22—C21 | 1.377 (4) | C6—C7 | 1.488 (4) |
C22—H22A | 0.9300 | F1'—C3' | 1.359 (4) |
C8—C9 | 1.518 (4) | C13'—C14' | 1.404 (5) |
C8—C7 | 1.519 (4) | C13'—H35A | 0.9300 |
C8—H8A | 0.9800 | C7—O1 | 1.204 (4) |
O3'—C16' | 1.191 (3) | C14—C13 | 1.409 (5) |
C9—H9A | 0.9700 | C14—H14A | 0.9300 |
C9—H9B | 0.9700 | C14'—H36A | 0.9300 |
C19'—C20' | 1.368 (4) | C5—C4 | 1.372 (6) |
C19'—C18' | 1.382 (4) | C5—H5B | 0.9300 |
C19'—H41A | 0.9300 | F1—C3 | 1.366 (5) |
C11—N3 | 1.375 (4) | C5'—C4' | 1.353 (6) |
C11—C10 | 1.388 (4) | C5'—H27A | 0.9300 |
C11—C12 | 1.392 (5) | C12—C13 | 1.358 (5) |
C8'—C7' | 1.514 (4) | C12—H12A | 0.9300 |
C8'—C9' | 1.515 (4) | C4'—C3' | 1.361 (6) |
C8'—H30A | 0.9800 | C4'—H26A | 0.9300 |
C10'—C11' | 1.389 (4) | C2'—C3' | 1.363 (6) |
C10'—C15' | 1.394 (4) | C2'—H24A | 0.9300 |
C15—C14 | 1.365 (5) | C13—H13A | 0.9300 |
C15—C10 | 1.385 (4) | C4—C3 | 1.357 (7) |
C15—H15A | 0.9300 | C4—H4A | 0.9300 |
C9'—H31A | 0.9700 | C2—C3 | 1.352 (6) |
C9'—H31B | 0.9700 | C2—H2B | 0.9300 |
C16—O2—C8 | 115.0 (2) | C19'—C20'—C21' | 121.6 (3) |
C10—N1—N2 | 110.8 (2) | C19'—C20'—Cl2' | 118.6 (2) |
C10—N1—C9 | 130.7 (2) | C21'—C20'—Cl2' | 119.8 (3) |
N2—N1—C9 | 118.4 (3) | C20'—C21'—C22' | 118.0 (3) |
N3'—N2'—N1' | 108.7 (2) | C20'—C21'—H43A | 121.0 |
C16'—O2'—C8' | 115.5 (2) | C22'—C21'—H43A | 121.0 |
N2'—N1'—C10' | 110.3 (2) | C17'—C22'—C21' | 122.2 (3) |
N2'—N1'—C9' | 118.8 (2) | C17'—C22'—H44A | 118.9 |
C10'—N1'—C9' | 130.9 (2) | C21'—C22'—H44A | 118.9 |
C19—C18—C17 | 121.2 (3) | C22—C21—C20 | 119.2 (3) |
C19—C18—Cl1 | 116.4 (2) | C22—C21—H21A | 120.4 |
C17—C18—Cl1 | 122.5 (2) | C20—C21—H21A | 120.4 |
C22—C17—C18 | 118.0 (3) | C19—C20—C21 | 120.5 (3) |
C22—C17—C16 | 120.3 (3) | C19—C20—Cl2 | 118.6 (3) |
C18—C17—C16 | 121.7 (3) | C21—C20—Cl2 | 120.9 (3) |
O3—C16—O2 | 123.1 (3) | C6'—C1'—C2' | 121.1 (3) |
O3—C16—C17 | 126.3 (3) | C6'—C1'—H23A | 119.4 |
O2—C16—C17 | 110.7 (3) | C2'—C1'—H23A | 119.4 |
C18—C19—C20 | 119.7 (3) | N3'—C11'—C12' | 130.7 (3) |
C18—C19—H19A | 120.2 | N3'—C11'—C10' | 108.5 (3) |
C20—C19—H19A | 120.2 | C12'—C11'—C10' | 120.8 (3) |
N3—N2—N1 | 108.4 (3) | O1'—C7'—C6' | 122.2 (3) |
N2'—N3'—C11' | 108.5 (2) | O1'—C7'—C8' | 120.3 (3) |
C21—C22—C17 | 121.5 (3) | C6'—C7'—C8' | 117.3 (3) |
C21—C22—H22A | 119.3 | C6—C1—C2 | 121.4 (4) |
C17—C22—H22A | 119.3 | C6—C1—H1A | 119.3 |
O2—C8—C9 | 106.8 (2) | C2—C1—H1A | 119.3 |
O2—C8—C7 | 110.1 (2) | C1'—C6'—C5' | 119.0 (3) |
C9—C8—C7 | 111.5 (2) | C1'—C6'—C7' | 123.3 (3) |
O2—C8—H8A | 109.5 | C5'—C6'—C7' | 117.8 (3) |
C9—C8—H8A | 109.5 | C13'—C12'—C11' | 117.2 (3) |
C7—C8—H8A | 109.5 | C13'—C12'—H34A | 121.4 |
N1—C9—C8 | 114.2 (2) | C11'—C12'—H34A | 121.4 |
N1—C9—H9A | 108.7 | C1—C6—C5 | 118.6 (3) |
C8—C9—H9A | 108.7 | C1—C6—C7 | 123.3 (3) |
N1—C9—H9B | 108.7 | C5—C6—C7 | 118.0 (4) |
C8—C9—H9B | 108.7 | C12'—C13'—C14' | 122.0 (3) |
H9A—C9—H9B | 107.6 | C12'—C13'—H35A | 119.0 |
C20'—C19'—C18' | 119.3 (3) | C14'—C13'—H35A | 119.0 |
C20'—C19'—H41A | 120.3 | O1—C7—C6 | 122.3 (3) |
C18'—C19'—H41A | 120.3 | O1—C7—C8 | 119.8 (3) |
N3—C11—C10 | 108.7 (3) | C6—C7—C8 | 117.7 (3) |
N3—C11—C12 | 130.6 (3) | C15—C14—C13 | 121.1 (4) |
C10—C11—C12 | 120.7 (3) | C15—C14—H14A | 119.4 |
O2'—C8'—C7' | 110.3 (3) | C13—C14—H14A | 119.4 |
O2'—C8'—C9' | 106.7 (2) | C15'—C14'—C13' | 121.5 (3) |
C7'—C8'—C9' | 111.6 (3) | C15'—C14'—H36A | 119.3 |
O2'—C8'—H30A | 109.4 | C13'—C14'—H36A | 119.3 |
C7'—C8'—H30A | 109.4 | C4—C5—C6 | 120.8 (4) |
C9'—C8'—H30A | 109.4 | C4—C5—H5B | 119.6 |
N1'—C10'—C11' | 103.9 (3) | C6—C5—H5B | 119.6 |
N1'—C10'—C15' | 133.8 (3) | C4'—C5'—C6' | 120.9 (4) |
C11'—C10'—C15' | 122.3 (3) | C4'—C5'—H27A | 119.5 |
C14—C15—C10 | 116.2 (3) | C6'—C5'—H27A | 119.5 |
C14—C15—H15A | 121.9 | C13—C12—C11 | 116.5 (4) |
C10—C15—H15A | 121.9 | C13—C12—H12A | 121.8 |
N1'—C9'—C8' | 114.3 (2) | C11—C12—H12A | 121.8 |
N1'—C9'—H31A | 108.7 | C5'—C4'—C3' | 118.6 (4) |
C8'—C9'—H31A | 108.7 | C5'—C4'—H26A | 120.7 |
N1'—C9'—H31B | 108.7 | C3'—C4'—H26A | 120.7 |
C8'—C9'—H31B | 108.7 | C3'—C2'—C1' | 117.2 (4) |
H31A—C9'—H31B | 107.6 | C3'—C2'—H24A | 121.4 |
N1—C10—C15 | 133.7 (3) | C1'—C2'—H24A | 121.4 |
N1—C10—C11 | 103.5 (3) | C12—C13—C14 | 122.7 (4) |
C15—C10—C11 | 122.8 (3) | C12—C13—H13A | 118.7 |
N2—N3—C11 | 108.6 (3) | C14—C13—H13A | 118.7 |
C19'—C18'—C17' | 121.3 (3) | F1'—C3'—C4' | 119.7 (5) |
C19'—C18'—Cl1' | 116.7 (2) | F1'—C3'—C2' | 117.2 (5) |
C17'—C18'—Cl1' | 122.0 (2) | C4'—C3'—C2' | 123.1 (4) |
C14'—C15'—C10' | 116.2 (3) | C3—C4—C5 | 118.2 (4) |
C14'—C15'—H37A | 121.9 | C3—C4—H4A | 120.9 |
C10'—C15'—H37A | 121.9 | C5—C4—H4A | 120.9 |
O3'—C16'—O2' | 122.6 (3) | C3—C2—C1 | 117.2 (4) |
O3'—C16'—C17' | 127.4 (3) | C3—C2—H2B | 121.4 |
O2'—C16'—C17' | 110.1 (3) | C1—C2—H2B | 121.4 |
C18'—C17'—C22' | 117.5 (3) | C2—C3—C4 | 123.8 (4) |
C18'—C17'—C16' | 122.3 (3) | C2—C3—F1 | 117.2 (5) |
C22'—C17'—C16' | 120.2 (3) | C4—C3—F1 | 119.0 (5) |
N3'—N2'—N1'—C10' | −0.2 (3) | C18'—C19'—C20'—Cl2' | −177.7 (2) |
N3'—N2'—N1'—C9' | −178.9 (2) | C19'—C20'—C21'—C22' | −1.2 (5) |
C19—C18—C17—C22 | 0.3 (4) | Cl2'—C20'—C21'—C22' | 177.8 (3) |
Cl1—C18—C17—C22 | 178.4 (2) | C18'—C17'—C22'—C21' | 1.7 (5) |
C19—C18—C17—C16 | 178.9 (3) | C16'—C17'—C22'—C21' | −177.0 (3) |
Cl1—C18—C17—C16 | −2.9 (4) | C20'—C21'—C22'—C17' | −0.3 (5) |
C8—O2—C16—O3 | −2.9 (4) | C17—C22—C21—C20 | −0.6 (5) |
C8—O2—C16—C17 | 177.4 (2) | C18—C19—C20—C21 | 0.1 (5) |
C22—C17—C16—O3 | 144.0 (3) | C18—C19—C20—Cl2 | 179.4 (2) |
C18—C17—C16—O3 | −34.6 (5) | C22—C21—C20—C19 | 0.4 (5) |
C22—C17—C16—O2 | −36.3 (4) | C22—C21—C20—Cl2 | −178.9 (2) |
C18—C17—C16—O2 | 145.0 (3) | N2'—N3'—C11'—C12' | −179.7 (3) |
C17—C18—C19—C20 | −0.4 (4) | N2'—N3'—C11'—C10' | −0.2 (3) |
Cl1—C18—C19—C20 | −178.7 (2) | N1'—C10'—C11'—N3' | 0.1 (3) |
C10—N1—N2—N3 | 0.8 (3) | C15'—C10'—C11'—N3' | 179.2 (3) |
C9—N1—N2—N3 | 179.5 (2) | N1'—C10'—C11'—C12' | 179.6 (3) |
N1'—N2'—N3'—C11' | 0.3 (3) | C15'—C10'—C11'—C12' | −1.3 (5) |
C18—C17—C22—C21 | 0.3 (5) | O2'—C8'—C7'—O1' | 13.7 (4) |
C16—C17—C22—C21 | −178.4 (3) | C9'—C8'—C7'—O1' | −104.7 (4) |
C16—O2—C8—C9 | 161.2 (2) | O2'—C8'—C7'—C6' | −171.4 (2) |
C16—O2—C8—C7 | −77.6 (3) | C9'—C8'—C7'—C6' | 70.2 (3) |
C10—N1—C9—C8 | −82.4 (4) | C2'—C1'—C6'—C5' | 1.2 (5) |
N2—N1—C9—C8 | 99.1 (3) | C2'—C1'—C6'—C7' | −176.9 (3) |
O2—C8—C9—N1 | 71.7 (3) | O1'—C7'—C6'—C1' | −157.0 (4) |
C7—C8—C9—N1 | −48.7 (3) | C8'—C7'—C6'—C1' | 28.3 (4) |
C16'—O2'—C8'—C7' | 79.9 (3) | O1'—C7'—C6'—C5' | 24.8 (5) |
C16'—O2'—C8'—C9' | −158.7 (3) | C8'—C7'—C6'—C5' | −149.9 (3) |
N2'—N1'—C10'—C11' | 0.1 (3) | N3'—C11'—C12'—C13' | −179.3 (3) |
C9'—N1'—C10'—C11' | 178.5 (3) | C10'—C11'—C12'—C13' | 1.3 (5) |
N2'—N1'—C10'—C15' | −178.9 (3) | C2—C1—C6—C5 | −0.2 (5) |
C9'—N1'—C10'—C15' | −0.4 (5) | C2—C1—C6—C7 | −178.7 (3) |
N2'—N1'—C9'—C8' | −100.9 (3) | C11'—C12'—C13'—C14' | −0.3 (5) |
C10'—N1'—C9'—C8' | 80.8 (4) | C1—C6—C7—O1 | 151.4 (3) |
O2'—C8'—C9'—N1' | −70.1 (3) | C5—C6—C7—O1 | −27.2 (5) |
C7'—C8'—C9'—N1' | 50.5 (3) | C1—C6—C7—C8 | −33.1 (4) |
N2—N1—C10—C15 | 178.8 (3) | C5—C6—C7—C8 | 148.3 (3) |
C9—N1—C10—C15 | 0.3 (5) | O2—C8—C7—O1 | −20.7 (4) |
N2—N1—C10—C11 | −1.0 (3) | C9—C8—C7—O1 | 97.6 (3) |
C9—N1—C10—C11 | −179.5 (3) | O2—C8—C7—C6 | 163.7 (2) |
C14—C15—C10—N1 | 180.0 (3) | C9—C8—C7—C6 | −77.9 (3) |
C14—C15—C10—C11 | −0.3 (5) | C10—C15—C14—C13 | −0.7 (5) |
N3—C11—C10—N1 | 0.8 (3) | C10'—C15'—C14'—C13' | 0.7 (5) |
C12—C11—C10—N1 | −179.7 (3) | C12'—C13'—C14'—C15' | −0.7 (5) |
N3—C11—C10—C15 | −179.0 (3) | C1—C6—C5—C4 | 1.0 (6) |
C12—C11—C10—C15 | 0.5 (5) | C7—C6—C5—C4 | 179.6 (4) |
N1—N2—N3—C11 | −0.2 (4) | C1'—C6'—C5'—C4' | −1.5 (5) |
C10—C11—N3—N2 | −0.4 (4) | C7'—C6'—C5'—C4' | 176.8 (3) |
C12—C11—N3—N2 | −179.8 (3) | N3—C11—C12—C13 | 179.8 (4) |
C20'—C19'—C18'—C17' | 0.2 (4) | C10—C11—C12—C13 | 0.4 (5) |
C20'—C19'—C18'—Cl1' | 178.1 (2) | C6'—C5'—C4'—C3' | 0.0 (6) |
N1'—C10'—C15'—C14' | 179.0 (3) | C6'—C1'—C2'—C3' | 0.5 (5) |
C11'—C10'—C15'—C14' | 0.2 (4) | C11—C12—C13—C14 | −1.5 (6) |
C8'—O2'—C16'—O3' | 2.5 (5) | C15—C14—C13—C12 | 1.7 (6) |
C8'—O2'—C16'—C17' | −178.4 (3) | C5'—C4'—C3'—F1' | −179.0 (3) |
C19'—C18'—C17'—C22' | −1.7 (4) | C5'—C4'—C3'—C2' | 1.9 (7) |
Cl1'—C18'—C17'—C22' | −179.4 (2) | C1'—C2'—C3'—F1' | 178.8 (3) |
C19'—C18'—C17'—C16' | 177.0 (3) | C1'—C2'—C3'—C4' | −2.1 (6) |
Cl1'—C18'—C17'—C16' | −0.8 (4) | C6—C5—C4—C3 | −0.2 (7) |
O3'—C16'—C17'—C18' | 34.4 (5) | C6—C1—C2—C3 | −1.4 (6) |
O2'—C16'—C17'—C18' | −144.7 (3) | C1—C2—C3—C4 | 2.3 (7) |
O3'—C16'—C17'—C22' | −147.0 (4) | C1—C2—C3—F1 | −179.0 (3) |
O2'—C16'—C17'—C22' | 33.9 (4) | C5—C4—C3—C2 | −1.5 (8) |
C18'—C19'—C20'—C21' | 1.2 (5) | C5—C4—C3—F1 | 179.8 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
C9—H9A···N3′i | 0.97 | 2.46 | 3.191 (4) | 132 |
C4′—H26A···Cl1ii | 0.93 | 2.73 | 3.632 (5) | 164 |
C9′—H31B···N3iii | 0.97 | 2.58 | 3.323 (4) | 134 |
Symmetry codes: (i) −x−1, y−1/2, −z+3/2; (ii) −x−1, y+1/2, −z+3/2; (iii) −x, y+1/2, −z+3/2. |
Experimental details
Crystal data | |
Chemical formula | C22H14Cl2FN3O3 |
Mr | 458.26 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 293 |
a, b, c (Å) | 11.9859 (7), 25.1527 (16), 13.8358 (9) |
β (°) | 98.647 (1) |
V (Å3) | 4123.8 (4) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.35 |
Crystal size (mm) | 0.34 × 0.30 × 0.14 |
Data collection | |
Diffractometer | Siemens SMART 1000 CCD area-detector |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.889, 0.952 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 23035, 8111, 4644 |
Rint | 0.039 |
(sin θ/λ)max (Å−1) | 0.618 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.060, 0.151, 1.03 |
No. of reflections | 8111 |
No. of parameters | 559 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.22, −0.17 |
Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 1997a), SHELXL97 (Sheldrick, 1997a), SHELXTL (Sheldrick, 1997b).
D—H···A | D—H | H···A | D···A | D—H···A |
C9—H9A···N3'i | 0.97 | 2.463 | 3.191 (4) | 131.65 |
C4'—H26A···Cl1ii | 0.93 | 2.730 | 3.632 (5) | 163.86 |
C9'—H31B···N3iii | 0.97 | 2.579 | 3.323 (4) | 133.72 |
Symmetry codes: (i) −x−1, y−1/2, −z+3/2; (ii) −x−1, y+1/2, −z+3/2; (iii) −x, y+1/2, −z+3/2. |
Recently we have reported the structure of 3-(benzotriazol-1-yl)-1-(4-chlorophenyl)-1-oxopropan-2-yl 2-chlorobenzoate (II) (Zhang et al., 2006). As part of our ongoing studies of searching for triazole derivatives with higher pharmacological activities, the title compound, (I), was synthesized and its structure is presented here.
All bond lengths and angles are within normal ranges (Allen et al., 1987) and are comparable with those in the related compound, (II). In the molecule of (I), the asymmetric unit contains two molecules, A and B. The benzotriazole system is essentially planar, with a dihedral of 0.70 (2) and 0.73 (2)/% between the triazole rings (N1—N3/C10/C11 and N1'-N3'/C10'/C11') and benzne rings (C10—C15 and C10'-C15') in A and B, respectively. In A, the mean plane of the benzotriazole group makes dihedral angles of 17.55 (2) and 17.02 (1)/% with the C1—C6 and C17—C22 benzene rings, respectively. The corresponding dihedral angles in B are 26.66 (1) and 11.21 (1)/%. The dihedral angles between the latter two benzene rings are 30.88 (2) and 32.44 (2)/% in A and B, respectively.
In the crystal structure, the intermolecular C9—H9A···N3', C9'-H31B···N3 and C4'-H26A···Cl1 hydrogen bonds link the molecules, forming infinite chains along the a axis. The packing is further stabilized by π-π interactions, with Cg1···Cg7 (x, 1/2 - y, -1/2 + z) and Cg2···Cg6 (-x, 1 - y, 2 - z) distances of 3.710 (1) and 3.661 (1) /%A, respectively (Cg1, Cg2, Cg6 and Cg7 are the centroids of the rings N1—N3/C10/C11, N1'-N3'/C10'/C11', C10'-C15' and C17—C22, respectively).