2-(1H-Benzotriazol-1-yl)-1-(4-fluoro­benzo­yl)ethyl 2,4-dichloro­benzoate

Bi, S.; Li, J.; Zeng, W.-L.; Wan, J.

doi:10.1107/S1600536807047046

2-(1H-Benzotriazol-1-yl)-1-(4-fluorobenzoyl)ethyl 2,4-dichlorobenzoate

In the title compound, C₂₂H₁₄Cl₂FN₃O₃, the two molecules in the asymmetric unit are linked into infinite chains along the a axis by intermolecular C—H

N and C—H

Cl hydrogen bonds.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807047046/sg2192sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807047046/sg2192Isup2.hkl Contains datablock I

CCDC reference: 667258

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.005 Å
R factor = 0.060
wR factor = 0.151
Data-to-parameter ratio = 14.5

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.59 Ratio
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         C4
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C3
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C3'
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C6'
PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...          5
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          1
              C22 H14 Cl2 F N3 O3

Alert level G
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K
PLAT793_ALERT_1_G Check the Absolute Configuration of C8     = ...          S
PLAT793_ALERT_1_G Check the Absolute Configuration of C8'    = ...          R

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   8 ALERT level C = Check and explain
   4 ALERT level G = General alerts; check

   4 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   5 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Comment top

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).

Related literature top

For related literature, see: Zhang et al. (2006); Allen et al. (1987).

Experimental top

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.

Structure description top

For related literature, see: Zhang et al. (2006); Allen et al. (1987).

Computing details top

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).

Figures top

	Fig. 1. The structure of the compound (I) showing 50% probability displacement ellipsoids and the atom numbering scheme.
	Fig. 2. A packing diagram of (I), viewed down the b axis. Hydrogen bonds are indicated by dashed lines.

2-(1H-Benzotriazol-1-yl)-1-(4-fluorobenzoyl)ethyl 2,4-dichlorobenzoate top

Crystal data top

C₂₂H₁₄Cl₂FN₃O₃	F(000) = 1872
M_r = 458.26	D_x = 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

Data collection top

Siemens SMART 1000 CCD area-detector diffractometer	8111 independent reflections
Radiation source: fine-focus sealed tube	4644 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.039
Detector resolution: 8.33 pixels mm^-1	θ_max = 26.0°, θ_min = 1.6°
ω scans	h = −14→8
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −31→31
T_min = 0.889, T_max = 0.952	l = −16→17
23035 measured reflections

Refinement top

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(F_o²) + (0.0623P)² + 0.2266P] where P = (F_o² + 2F_c²)/3
8111 reflections	(Δ/σ)_max = 0.001
559 parameters	Δρ_max = 0.22 e Å⁻³
0 restraints	Δρ_min = −0.17 e Å⁻³

Crystal data top

C₂₂H₁₄Cl₂FN₃O₃	V = 4123.8 (4) Å³
M_r = 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)°

Data collection top

Siemens SMART 1000 CCD area-detector diffractometer	8111 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	4644 reflections with I > 2σ(I)
T_min = 0.889, T_max = 0.952	R_int = 0.039
23035 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.060	0 restraints
wR(F²) = 0.151	H-atom parameters constrained
S = 1.03	Δρ_max = 0.22 e Å⁻³
8111 reflections	Δρ_min = −0.17 e Å⁻³
559 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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
M_r	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)
T_min, T_max	0.889, 0.952
No. of measured, independent and observed [I > 2σ(I)] reflections	23035, 8111, 4644
R_int	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
Δρ_max, Δρ_min (e Å⁻³)	0.22, −0.17

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 1997a), SHELXL97 (Sheldrick, 1997a), SHELXTL (Sheldrick, 1997b).