(Z)-3-(4-Chloro­phen­yl)-1-(2,4-difluoro­phen­yl)-2-(1H-1,2,4-triazol-1-yl)prop-2-en-1-one

Peng, X.-M.; Yin, B.-T.; Zhou, C.-H.

doi:10.1107/S1600536812022118

organic compounds

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ISSN: 2056-9890

Volume 68| Part 6| June 2012| Page o1828

doi:10.1107/S1600536812022118

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(Z)-3-(4-Chlorophenyl)-1-(2,4-difluorophenyl)-2-(1H-1,2,4-triazol-1-yl)prop-2-en-1-one

Xin-Mei Peng,^a Ben-Tao Yin ^a and Cheng-He Zhou ^a ^*

^aLaboratory of Bioorganic & Medicinal Chemistry, School of Chemistry and Chemical Engineering, Southwest University, Chongqing 400715, People's Republic of China
^*Correspondence e-mail: zhouch@swu.edu.cn

(Received 6 May 2012; accepted 16 May 2012; online 19 May 2012)

The asymmetric unit of the title compound, C₁₇H₁₀ClF₂N₃O, contains three independent molecules. In each molecule, the C=C bond has a cis conformation with respect to the triazole and chlorophenyl groups. The dihedral angles formed by the triazole ring with the diflurophenyl and chlorophenyl benzene rings, respectively, are 20.10 (14) and 73.22 (15), 25.31 (15) and 84.44 (15), and 16.44 (13) and 61.72 (14)° in the three molecules while the dihedral angles between the benzene rings are 66.54 (13), 85.82 (12) and 58.37 (12)°.

Related literature

For applications of triazole compounds in chemistry and medicinal chemistry, see: Bai et al. (2007 ); Chang et al. (2011 ); Wang & Zhou (2011 ); Zhou & Wang (2012 ). For the pharmacological activity of chalcones, see: Jin et al. (2010 ). For the synthesis of the title compound, see: Yan et al. (2009 ). For related structures, see: Wang et al. (2009 ); Yan et al. (2009).

Experimental

Crystal data

C₁₇H₁₀ClF₂N₃O
M_r = 345.73
Monoclinic, P 2₁ /c
a = 17.237 (3) Å
b = 10.466 (2) Å
c = 26.554 (5) Å
β = 102.378 (4)°
V = 4679.2 (16) Å³
Z = 12
Mo Kα radiation
μ = 0.28 mm⁻¹
T = 296 K
0.23 × 0.21 × 0.17 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.939, T_max = 0.955
25352 measured reflections
9200 independent reflections
5656 reflections with I > 2σ(I)
R_int = 0.032

Refinement

R[F² > 2σ(F²)] = 0.045
wR(F²) = 0.133
S = 1.01
9200 reflections
650 parameters
H-atom parameters constrained
Δρ_max = 0.34 e Å⁻³
Δρ_min = −0.35 e Å⁻³

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009 ); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812022118/lh5474sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812022118/lh5474Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812022118/lh5474Isup3.cml

checkCIF report

Comment top

Triazole-based derivatives exhibit extensive potential applications in chemical, medincinal, biological, supramolecular and material sciences (Bai et al., 2007; Chang et al., 2011; Wang et al., 2011; Zhou et al., 2012) and therefore related research has been attracting great attention. Our interest is to invesigate the hybrids of triazole with chalcones (Jin et al., 2010). Some triazole-based chalcones have been reported in our group (Wang et al., 2009; Yan et al., 2009). Herein, the crystal structure of the title compound (I) is reported.

The asymmetric unit of (I) is shown in Fig. 1. In each, the C═C bond has a cis conformation with respect the the triazole and chlorophenyl groups. The dihedral angles formed in each molecule by the triazole ring with the diflurophenyl and chlorophenyl benzene rings respectively, is 20.10 (14) and 73.22 (15) Å [N1/N2/N3/C9/C10 with C12-C17 and C1-C6], 25.31 (15) and 84.44 (15)Å [N4/N5/N6/C25/C26 with C29-C34 and C18-C23], 16.44 (13) and 61.72 (14)Å [N7/N8/N9/C43C44 with C46-C51 and C35-C40]. The dihedral angles between the two benzene rings in each molecule is 66.54 (13) [C1-C6 and C12-C17], 85.82 (12)Å [C18-C23 and C29-C34] and 58.37 (12)Å [C35-C40 and C46-C51].

Related literature top

For applications of triazole compounds in chemistry and medicinal chemistry, see: Bai et al. (2007); Chang et al. (2011); Wang & Zhou (2011); Zhou & Wang (2012). For the pharmacological activity of chalcones, see: Jin et al. (2010). For the synthesis of the title compound, see: Yan et al. (2009). For related structures, see: Wang et al. (2009); Yan et al. (2009).

Experimental top

The title compound was prepared according to the procedure of Yan et al. (2009). Single crystals were grown from slow evaporation of a solution of (I) in ethyl acetate and petroleum ether (1:10, V/V) at room temperature.

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. The asymmetric unit of (I), showing the displacement ellipsoids drawn at the 30% probability level.

(Z)-3-(4-Chlorophenyl)-1-(2,4-difluorophenyl)-2-(1H-1,2,4- triazol-1-yl)prop-2-en-1-one top

Crystal data top

C₁₇H₁₀ClF₂N₃O	F(000) = 2112
M_r = 345.73	D_x = 1.472 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5332 reflections
a = 17.237 (3) Å	θ = 2.2–22.9°
b = 10.466 (2) Å	µ = 0.28 mm⁻¹
c = 26.554 (5) Å	T = 296 K
β = 102.378 (4)°	Block, colorless
V = 4679.2 (16) Å³	0.23 × 0.21 × 0.17 mm
Z = 12

Data collection top

Bruker APEXII CCD diffractometer	9200 independent reflections
Radiation source: fine-focus sealed tube	5656 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.032
ϕ and ω scans	θ_max = 26.0°, θ_min = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −20→21
T_min = 0.939, T_max = 0.955	k = −12→10
25352 measured reflections	l = −32→30

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.045	H-atom parameters constrained
wR(F²) = 0.133	w = 1/[σ²(F_o²) + (0.0626P)² + 0.7017P] where P = (F_o² + 2F_c²)/3
S = 1.01	(Δ/σ)_max = 0.001
9200 reflections	Δρ_max = 0.34 e Å⁻³
650 parameters	Δρ_min = −0.35 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0015 (2)

Crystal data top

C₁₇H₁₀ClF₂N₃O	V = 4679.2 (16) Å³
M_r = 345.73	Z = 12
Monoclinic, P2₁/c	Mo Kα radiation
a = 17.237 (3) Å	µ = 0.28 mm⁻¹
b = 10.466 (2) Å	T = 296 K
c = 26.554 (5) Å	0.23 × 0.21 × 0.17 mm
β = 102.378 (4)°

Data collection top

Bruker APEXII CCD diffractometer	9200 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	5656 reflections with I > 2σ(I)
T_min = 0.939, T_max = 0.955	R_int = 0.032
25352 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	0 restraints
wR(F²) = 0.133	H-atom parameters constrained
S = 1.01	Δρ_max = 0.34 e Å⁻³
9200 reflections	Δρ_min = −0.35 e Å⁻³
650 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
F1	0.20468 (8)	0.35283 (12)	0.14981 (5)	0.0668 (4)
F2	0.05967 (9)	0.66430 (13)	0.21328 (7)	0.0874 (5)
F3	0.78892 (9)	0.56839 (13)	0.52214 (5)	0.0708 (4)
F4	0.92930 (10)	0.25782 (15)	0.45456 (8)	0.1080 (6)
F5	0.92861 (9)	0.25932 (13)	0.09951 (7)	0.0901 (5)
F6	0.80518 (9)	0.56279 (12)	0.18279 (5)	0.0717 (4)
C1	0.52331 (16)	0.0907 (3)	0.29462 (11)	0.0747 (7)
C2	0.49247 (17)	0.2060 (3)	0.30181 (12)	0.0815 (8)
H2A	0.5243	0.2694	0.3202	0.098*
C3	0.41327 (15)	0.2288 (2)	0.28162 (10)	0.0694 (7)
H3A	0.3922	0.3083	0.2868	0.083*
C4	0.36428 (13)	0.1379 (2)	0.25404 (8)	0.0509 (5)
C5	0.39820 (17)	0.0207 (2)	0.24830 (11)	0.0806 (8)
H5A	0.3668	−0.0441	0.2306	0.097*
C6	0.47705 (18)	−0.0022 (3)	0.26816 (13)	0.0909 (9)
H6A	0.4988	−0.0815	0.2635	0.109*
C7	0.28127 (13)	0.1712 (2)	0.23551 (8)	0.0506 (5)
H7A	0.2678	0.2520	0.2454	0.061*
C8	0.22060 (13)	0.10637 (19)	0.20677 (8)	0.0474 (5)
C9	0.26059 (15)	−0.1494 (2)	0.13538 (10)	0.0628 (7)
H9A	0.2812	−0.1870	0.1093	0.075*
C10	0.20371 (17)	−0.1289 (2)	0.19568 (12)	0.0769 (8)
H10A	0.1755	−0.1442	0.2213	0.092*
C11	0.13747 (13)	0.1504 (2)	0.19983 (8)	0.0492 (5)
C12	0.11973 (12)	0.2886 (2)	0.20359 (8)	0.0460 (5)
C13	0.15149 (13)	0.3843 (2)	0.17871 (8)	0.0480 (5)
C14	0.13213 (14)	0.5102 (2)	0.18068 (9)	0.0560 (6)
H14A	0.1541	0.5723	0.1629	0.067*
C15	0.07866 (14)	0.5404 (2)	0.21011 (10)	0.0604 (6)
C16	0.04492 (14)	0.4512 (2)	0.23620 (10)	0.0637 (7)
H16A	0.0093	0.4750	0.2563	0.076*
C17	0.06485 (13)	0.3261 (2)	0.23190 (9)	0.0566 (6)
H17A	0.0408	0.2641	0.2485	0.068*
C18	0.45770 (14)	0.8091 (3)	0.38261 (11)	0.0663 (7)
C19	0.49635 (14)	0.8600 (2)	0.42844 (11)	0.0712 (7)
H19A	0.4688	0.9098	0.4478	0.085*
C20	0.57613 (14)	0.8375 (2)	0.44587 (10)	0.0660 (7)
H20A	0.6026	0.8735	0.4768	0.079*
C21	0.61753 (12)	0.76197 (19)	0.41791 (9)	0.0496 (5)
C22	0.57591 (14)	0.7066 (2)	0.37302 (10)	0.0659 (7)
H22A	0.6019	0.6516	0.3547	0.079*
C23	0.49680 (15)	0.7317 (3)	0.35512 (11)	0.0761 (8)
H23A	0.4698	0.6959	0.3242	0.091*
C24	0.70225 (12)	0.7339 (2)	0.43406 (8)	0.0491 (5)
H24A	0.7171	0.6526	0.4256	0.059*
C25	0.72815 (15)	1.0924 (2)	0.51513 (10)	0.0626 (6)
H25A	0.7157	1.1425	0.5412	0.075*
C26	0.75847 (19)	1.0413 (2)	0.44775 (11)	0.0860 (9)
H26A	0.7728	1.0434	0.4159	0.103*
C27	0.76129 (12)	0.80666 (19)	0.45894 (8)	0.0454 (5)
C28	0.84596 (13)	0.7695 (2)	0.46558 (8)	0.0495 (5)
C29	0.86721 (12)	0.6328 (2)	0.46420 (8)	0.0478 (5)
C30	0.92034 (13)	0.5955 (2)	0.43433 (10)	0.0598 (6)
H30A	0.9422	0.6573	0.4164	0.072*
C31	0.94140 (15)	0.4701 (3)	0.43059 (11)	0.0717 (7)
H31A	0.9762	0.4463	0.4099	0.086*
C32	0.91002 (15)	0.3813 (2)	0.45796 (11)	0.0697 (7)
C33	0.85911 (14)	0.4115 (2)	0.48906 (10)	0.0621 (6)
H33A	0.8393	0.3494	0.5080	0.075*
C34	0.83867 (12)	0.5369 (2)	0.49113 (9)	0.0507 (5)
C35	0.48083 (14)	0.8658 (3)	0.05895 (10)	0.0672 (7)
C36	0.53758 (16)	0.9580 (3)	0.06771 (10)	0.0712 (7)
H36A	0.5232	1.0434	0.0623	0.085*
C37	0.61618 (15)	0.9259 (2)	0.08456 (10)	0.0654 (7)
H37A	0.6545	0.9899	0.0905	0.078*
C38	0.63907 (13)	0.8001 (2)	0.09278 (9)	0.0535 (6)
C39	0.58004 (16)	0.7084 (3)	0.08339 (11)	0.0749 (8)
H39A	0.5940	0.6227	0.0882	0.090*
C40	0.50156 (16)	0.7403 (3)	0.06715 (12)	0.0795 (8)
H40A	0.4627	0.6771	0.0618	0.095*
C41	0.72159 (13)	0.7588 (2)	0.10696 (9)	0.0537 (6)
H41A	0.7306	0.6763	0.0965	0.064*
C42	0.78625 (13)	0.81873 (19)	0.13225 (8)	0.0486 (5)
C43	0.74745 (15)	1.0733 (2)	0.20480 (10)	0.0635 (7)
H43A	0.7235	1.1114	0.2292	0.076*
C44	0.81640 (15)	1.0507 (2)	0.15076 (10)	0.0627 (7)
H44A	0.8507	1.0644	0.1286	0.075*
C45	0.86757 (14)	0.7726 (2)	0.13301 (9)	0.0529 (6)
C46	0.88146 (12)	0.6337 (2)	0.12470 (8)	0.0470 (5)
C47	0.85120 (13)	0.5356 (2)	0.14879 (8)	0.0507 (5)
C48	0.86624 (13)	0.4091 (2)	0.14169 (9)	0.0555 (6)
H48A	0.8453	0.3444	0.1588	0.067*
C49	0.91392 (14)	0.3839 (2)	0.10796 (10)	0.0605 (6)
C50	0.94698 (14)	0.4753 (3)	0.08309 (10)	0.0646 (7)
H50A	0.9795	0.4536	0.0606	0.078*
C51	0.93108 (13)	0.6008 (2)	0.09209 (9)	0.0579 (6)
H51A	0.9541	0.6650	0.0760	0.069*
Cl1	0.62306 (5)	0.05800 (11)	0.31895 (4)	0.1276 (4)
Cl2	0.35746 (4)	0.84070 (10)	0.36066 (4)	0.1091 (3)
Cl3	0.38200 (4)	0.90807 (9)	0.03691 (4)	0.0978 (3)
N1	0.22974 (11)	−0.01526 (15)	0.18508 (7)	0.0500 (5)
N2	0.26661 (11)	−0.02714 (17)	0.14488 (7)	0.0547 (5)
N3	0.22279 (14)	−0.21717 (19)	0.16551 (10)	0.0817 (7)
N4	0.74910 (10)	0.93572 (15)	0.47265 (7)	0.0467 (4)
N5	0.72995 (12)	0.96812 (17)	0.51768 (7)	0.0587 (5)
N6	0.74517 (17)	1.1429 (2)	0.47318 (11)	0.0942 (8)
N7	0.78198 (11)	0.93912 (15)	0.15638 (7)	0.0489 (4)
N8	0.73630 (11)	0.95284 (17)	0.19205 (7)	0.0548 (5)
N9	0.79562 (13)	1.13848 (18)	0.18044 (9)	0.0696 (6)
O1	0.08400 (10)	0.07287 (15)	0.19375 (7)	0.0703 (5)
O2	0.89650 (9)	0.85179 (15)	0.46908 (7)	0.0690 (5)
O3	0.92184 (10)	0.84789 (16)	0.13720 (7)	0.0728 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
F1	0.0852 (10)	0.0554 (8)	0.0731 (9)	0.0047 (7)	0.0466 (8)	0.0060 (7)
F2	0.0891 (11)	0.0574 (9)	0.1196 (14)	0.0236 (8)	0.0306 (10)	−0.0069 (8)
F3	0.0855 (10)	0.0639 (9)	0.0737 (9)	0.0103 (7)	0.0411 (8)	0.0058 (7)
F4	0.1029 (13)	0.0660 (10)	0.1600 (18)	0.0361 (9)	0.0389 (12)	−0.0070 (10)
F5	0.0972 (12)	0.0578 (9)	0.1217 (14)	0.0124 (8)	0.0375 (10)	−0.0182 (9)
F6	0.0993 (11)	0.0597 (8)	0.0698 (9)	0.0010 (7)	0.0486 (8)	0.0020 (7)
C1	0.0620 (17)	0.089 (2)	0.0703 (18)	−0.0014 (16)	0.0085 (14)	0.0089 (16)
C2	0.0697 (19)	0.079 (2)	0.093 (2)	−0.0155 (16)	0.0105 (16)	−0.0116 (16)
C3	0.0668 (17)	0.0624 (16)	0.0796 (19)	−0.0030 (13)	0.0170 (14)	−0.0114 (13)
C4	0.0609 (14)	0.0462 (13)	0.0474 (13)	−0.0010 (11)	0.0155 (11)	0.0011 (10)
C5	0.0762 (19)	0.0583 (16)	0.095 (2)	0.0095 (14)	−0.0097 (16)	−0.0104 (15)
C6	0.080 (2)	0.0715 (19)	0.109 (2)	0.0242 (16)	−0.0054 (18)	−0.0060 (17)
C7	0.0635 (15)	0.0403 (12)	0.0516 (13)	0.0008 (11)	0.0203 (11)	0.0007 (10)
C8	0.0603 (14)	0.0358 (11)	0.0504 (13)	−0.0037 (10)	0.0213 (11)	0.0001 (9)
C9	0.0751 (17)	0.0405 (13)	0.0768 (17)	0.0004 (12)	0.0248 (14)	−0.0078 (12)
C10	0.098 (2)	0.0397 (14)	0.108 (2)	−0.0073 (13)	0.0561 (18)	0.0052 (14)
C11	0.0546 (13)	0.0476 (13)	0.0498 (13)	−0.0083 (11)	0.0211 (11)	−0.0019 (10)
C12	0.0453 (12)	0.0454 (12)	0.0489 (13)	−0.0030 (10)	0.0136 (10)	−0.0028 (10)
C13	0.0509 (13)	0.0481 (13)	0.0488 (13)	0.0009 (10)	0.0191 (11)	−0.0019 (10)
C14	0.0609 (15)	0.0461 (13)	0.0628 (15)	0.0013 (11)	0.0169 (12)	0.0022 (11)
C15	0.0559 (15)	0.0523 (15)	0.0716 (16)	0.0128 (12)	0.0104 (13)	−0.0089 (12)
C16	0.0534 (14)	0.0699 (17)	0.0732 (17)	0.0086 (12)	0.0251 (13)	−0.0118 (13)
C17	0.0502 (13)	0.0612 (15)	0.0630 (15)	−0.0028 (11)	0.0221 (12)	−0.0025 (11)
C18	0.0450 (13)	0.0761 (17)	0.0757 (18)	−0.0005 (12)	0.0081 (13)	−0.0074 (14)
C19	0.0517 (15)	0.0742 (17)	0.088 (2)	0.0079 (13)	0.0147 (14)	−0.0202 (15)
C20	0.0500 (14)	0.0764 (17)	0.0701 (17)	0.0039 (13)	0.0099 (12)	−0.0214 (13)
C21	0.0471 (13)	0.0438 (12)	0.0575 (14)	0.0006 (10)	0.0107 (11)	−0.0043 (10)
C22	0.0574 (15)	0.0715 (16)	0.0687 (17)	−0.0019 (13)	0.0131 (13)	−0.0196 (13)
C23	0.0577 (16)	0.096 (2)	0.0688 (18)	−0.0033 (15)	0.0013 (13)	−0.0230 (15)
C24	0.0492 (13)	0.0443 (12)	0.0545 (14)	0.0041 (10)	0.0131 (11)	−0.0022 (10)
C25	0.0736 (17)	0.0462 (15)	0.0695 (17)	0.0032 (12)	0.0188 (14)	−0.0100 (12)
C26	0.139 (3)	0.0516 (16)	0.085 (2)	0.0185 (16)	0.062 (2)	0.0197 (15)
C27	0.0529 (13)	0.0390 (12)	0.0460 (12)	0.0029 (10)	0.0141 (10)	0.0009 (9)
C28	0.0470 (13)	0.0525 (13)	0.0493 (13)	−0.0041 (11)	0.0110 (10)	−0.0030 (10)
C29	0.0383 (11)	0.0519 (13)	0.0518 (13)	0.0040 (10)	0.0065 (10)	−0.0028 (10)
C30	0.0436 (13)	0.0695 (16)	0.0689 (16)	0.0039 (12)	0.0178 (12)	0.0007 (12)
C31	0.0531 (15)	0.0789 (19)	0.086 (2)	0.0196 (14)	0.0214 (14)	−0.0113 (16)
C32	0.0599 (16)	0.0566 (16)	0.090 (2)	0.0202 (13)	0.0109 (15)	−0.0109 (14)
C33	0.0591 (15)	0.0538 (15)	0.0720 (17)	0.0072 (12)	0.0107 (13)	0.0035 (12)
C34	0.0461 (13)	0.0543 (14)	0.0530 (13)	0.0073 (10)	0.0133 (11)	−0.0021 (11)
C35	0.0549 (15)	0.0831 (19)	0.0667 (17)	−0.0069 (14)	0.0197 (13)	−0.0031 (14)
C36	0.0665 (17)	0.0618 (16)	0.0816 (19)	0.0002 (14)	0.0075 (14)	0.0038 (14)
C37	0.0626 (16)	0.0576 (15)	0.0721 (17)	−0.0108 (12)	0.0059 (13)	0.0026 (12)
C38	0.0561 (14)	0.0512 (14)	0.0550 (14)	−0.0074 (11)	0.0160 (11)	−0.0104 (11)
C39	0.0683 (18)	0.0578 (15)	0.097 (2)	−0.0115 (13)	0.0143 (15)	−0.0122 (14)
C40	0.0622 (18)	0.077 (2)	0.100 (2)	−0.0216 (15)	0.0173 (16)	−0.0139 (16)
C41	0.0628 (15)	0.0460 (13)	0.0543 (14)	−0.0061 (11)	0.0173 (12)	−0.0040 (10)
C42	0.0592 (14)	0.0384 (12)	0.0502 (13)	−0.0063 (10)	0.0165 (11)	0.0016 (10)
C43	0.0783 (18)	0.0427 (14)	0.0684 (16)	0.0042 (12)	0.0133 (14)	−0.0033 (12)
C44	0.0692 (16)	0.0396 (13)	0.0810 (18)	−0.0086 (12)	0.0201 (14)	0.0077 (12)
C45	0.0592 (15)	0.0503 (13)	0.0510 (14)	−0.0097 (11)	0.0159 (11)	0.0015 (10)
C46	0.0475 (12)	0.0463 (12)	0.0478 (12)	−0.0021 (10)	0.0117 (10)	0.0003 (10)
C47	0.0555 (14)	0.0523 (14)	0.0467 (13)	−0.0020 (11)	0.0164 (11)	−0.0036 (10)
C48	0.0587 (14)	0.0469 (13)	0.0605 (15)	−0.0021 (11)	0.0123 (12)	0.0019 (11)
C49	0.0589 (15)	0.0497 (14)	0.0719 (17)	0.0040 (12)	0.0117 (13)	−0.0118 (12)
C50	0.0548 (15)	0.0729 (18)	0.0718 (17)	0.0045 (13)	0.0260 (13)	−0.0102 (14)
C51	0.0512 (14)	0.0644 (16)	0.0603 (15)	−0.0047 (12)	0.0167 (12)	0.0004 (12)
Cl1	0.0659 (5)	0.1549 (9)	0.1484 (9)	0.0093 (5)	−0.0074 (5)	0.0063 (7)
Cl2	0.0478 (4)	0.1542 (8)	0.1166 (7)	0.0082 (5)	−0.0016 (4)	−0.0248 (6)
Cl3	0.0559 (4)	0.1225 (7)	0.1150 (7)	−0.0003 (4)	0.0183 (4)	0.0045 (5)
N1	0.0602 (12)	0.0345 (10)	0.0607 (12)	−0.0031 (8)	0.0250 (10)	0.0001 (8)
N2	0.0673 (13)	0.0431 (11)	0.0587 (12)	−0.0010 (9)	0.0246 (10)	−0.0015 (9)
N3	0.0952 (17)	0.0379 (11)	0.126 (2)	−0.0095 (11)	0.0542 (16)	−0.0073 (12)
N4	0.0548 (11)	0.0395 (10)	0.0483 (11)	0.0019 (8)	0.0165 (9)	0.0025 (8)
N5	0.0820 (14)	0.0457 (12)	0.0506 (12)	0.0018 (10)	0.0192 (10)	−0.0016 (9)
N6	0.143 (2)	0.0438 (13)	0.114 (2)	0.0119 (13)	0.0683 (19)	0.0111 (13)
N7	0.0567 (11)	0.0364 (10)	0.0544 (11)	−0.0046 (8)	0.0138 (9)	0.0038 (8)
N8	0.0693 (13)	0.0418 (11)	0.0559 (12)	0.0011 (9)	0.0193 (10)	0.0016 (9)
N9	0.0769 (15)	0.0384 (11)	0.0924 (16)	−0.0040 (10)	0.0157 (13)	0.0009 (11)
O1	0.0655 (11)	0.0531 (10)	0.0987 (14)	−0.0161 (9)	0.0317 (10)	−0.0087 (9)
O2	0.0545 (10)	0.0589 (10)	0.0935 (13)	−0.0102 (8)	0.0158 (9)	−0.0070 (9)
O3	0.0633 (11)	0.0564 (10)	0.1024 (14)	−0.0139 (9)	0.0257 (10)	−0.0045 (9)

Geometric parameters (Å, º) top

F1—C13	1.356 (2)	C25—N6	1.321 (3)
F2—C15	1.345 (3)	C25—H25A	0.9300
F3—C34	1.351 (2)	C26—N6	1.306 (3)
F4—C32	1.343 (3)	C26—N4	1.315 (3)
F5—C49	1.356 (3)	C26—H26A	0.9300
F6—C47	1.354 (2)	C27—N4	1.426 (3)
C1—C6	1.354 (4)	C27—C28	1.484 (3)
C1—C2	1.349 (4)	C28—O2	1.214 (2)
C1—Cl1	1.736 (3)	C28—C29	1.479 (3)
C2—C3	1.376 (4)	C29—C30	1.390 (3)
C2—H2A	0.9300	C29—C34	1.383 (3)
C3—C4	1.374 (3)	C30—C31	1.371 (3)
C3—H3A	0.9300	C30—H30A	0.9300
C4—C5	1.382 (3)	C31—C32	1.361 (4)
C4—C7	1.452 (3)	C31—H31A	0.9300
C5—C6	1.369 (4)	C32—C33	1.365 (3)
C5—H5A	0.9300	C33—C34	1.363 (3)
C6—H6A	0.9300	C33—H33A	0.9300
C7—C8	1.339 (3)	C35—C36	1.358 (3)
C7—H7A	0.9300	C35—C40	1.367 (4)
C8—N1	1.420 (3)	C35—Cl3	1.736 (3)
C8—C11	1.479 (3)	C36—C37	1.374 (3)
C9—N2	1.304 (3)	C36—H36A	0.9300
C9—N3	1.339 (3)	C37—C38	1.378 (3)
C9—H9A	0.9300	C37—H37A	0.9300
C10—N3	1.310 (3)	C38—C39	1.382 (3)
C10—N1	1.323 (3)	C38—C41	1.457 (3)
C10—H10A	0.9300	C39—C40	1.370 (4)
C11—O1	1.212 (2)	C39—H39A	0.9300
C11—C12	1.486 (3)	C40—H40A	0.9300
C12—C13	1.376 (3)	C41—C42	1.329 (3)
C12—C17	1.385 (3)	C41—H41A	0.9300
C13—C14	1.363 (3)	C42—N7	1.423 (3)
C14—C15	1.367 (3)	C42—C45	1.479 (3)
C14—H14A	0.9300	C43—N8	1.308 (3)
C15—C16	1.364 (3)	C43—N9	1.343 (3)
C16—C17	1.365 (3)	C43—H43A	0.9300
C16—H16A	0.9300	C44—N9	1.310 (3)
C17—H17A	0.9300	C44—N7	1.332 (3)
C18—C19	1.365 (3)	C44—H44A	0.9300
C18—C23	1.362 (3)	C45—O3	1.210 (3)
C18—Cl2	1.733 (2)	C45—C46	1.497 (3)
C19—C20	1.374 (3)	C46—C47	1.371 (3)
C19—H19A	0.9300	C46—C51	1.385 (3)
C20—C21	1.383 (3)	C47—C48	1.370 (3)
C20—H20A	0.9300	C48—C49	1.365 (3)
C21—C22	1.380 (3)	C48—H48A	0.9300
C21—C24	1.461 (3)	C49—C50	1.356 (3)
C22—C23	1.370 (3)	C50—C51	1.373 (3)
C22—H22A	0.9300	C50—H50A	0.9300
C23—H23A	0.9300	C51—H51A	0.9300
C24—C27	1.328 (3)	N1—N2	1.360 (2)
C24—H24A	0.9300	N4—N5	1.350 (2)
C25—N5	1.303 (3)	N7—N8	1.363 (2)

C6—C1—C2	120.6 (3)	C30—C29—C34	116.2 (2)
C6—C1—Cl1	118.5 (2)	C30—C29—C28	118.9 (2)
C2—C1—Cl1	120.8 (2)	C34—C29—C28	124.89 (19)
C3—C2—C1	119.2 (3)	C29—C30—C31	121.8 (2)
C3—C2—H2A	120.4	C29—C30—H30A	119.1
C1—C2—H2A	120.4	C31—C30—H30A	119.1
C2—C3—C4	122.2 (3)	C32—C31—C30	118.2 (2)
C2—C3—H3A	118.9	C32—C31—H31A	120.9
C4—C3—H3A	118.9	C30—C31—H31A	120.9
C5—C4—C3	116.6 (2)	C31—C32—F4	119.3 (2)
C5—C4—C7	125.8 (2)	C31—C32—C33	123.1 (2)
C3—C4—C7	117.6 (2)	F4—C32—C33	117.6 (3)
C4—C5—C6	121.4 (3)	C32—C33—C34	116.9 (2)
C4—C5—H5A	119.3	C32—C33—H33A	121.6
C6—C5—H5A	119.3	C34—C33—H33A	121.6
C1—C6—C5	120.0 (3)	F3—C34—C33	117.6 (2)
C1—C6—H6A	120.0	F3—C34—C29	118.71 (19)
C5—C6—H6A	120.0	C33—C34—C29	123.7 (2)
C8—C7—C4	131.6 (2)	C36—C35—C40	120.1 (3)
C8—C7—H7A	114.2	C36—C35—Cl3	119.7 (2)
C4—C7—H7A	114.2	C40—C35—Cl3	120.2 (2)
C7—C8—N1	123.0 (2)	C35—C36—C37	120.3 (2)
C7—C8—C11	122.05 (19)	C35—C36—H36A	119.8
N1—C8—C11	114.69 (19)	C37—C36—H36A	119.8
N2—C9—N3	115.7 (2)	C36—C37—C38	120.9 (2)
N2—C9—H9A	122.2	C36—C37—H37A	119.5
N3—C9—H9A	122.2	C38—C37—H37A	119.5
N3—C10—N1	111.3 (2)	C39—C38—C37	117.4 (2)
N3—C10—H10A	124.4	C39—C38—C41	118.7 (2)
N1—C10—H10A	124.4	C37—C38—C41	123.7 (2)
O1—C11—C8	119.8 (2)	C40—C39—C38	121.8 (3)
O1—C11—C12	119.9 (2)	C40—C39—H39A	119.1
C8—C11—C12	120.18 (18)	C38—C39—H39A	119.1
C13—C12—C17	116.3 (2)	C35—C40—C39	119.4 (2)
C13—C12—C11	124.56 (18)	C35—C40—H40A	120.3
C17—C12—C11	119.10 (19)	C39—C40—H40A	120.3
F1—C13—C14	117.20 (19)	C42—C41—C38	131.1 (2)
F1—C13—C12	118.81 (18)	C42—C41—H41A	114.4
C14—C13—C12	124.0 (2)	C38—C41—H41A	114.4
C15—C14—C13	116.5 (2)	C41—C42—N7	121.8 (2)
C15—C14—H14A	121.8	C41—C42—C45	122.9 (2)
C13—C14—H14A	121.8	N7—C42—C45	115.06 (19)
F2—C15—C14	117.5 (2)	N8—C43—N9	115.9 (2)
F2—C15—C16	119.5 (2)	N8—C43—H43A	122.1
C14—C15—C16	123.0 (2)	N9—C43—H43A	122.1
C15—C16—C17	118.1 (2)	N9—C44—N7	111.2 (2)
C15—C16—H16A	120.9	N9—C44—H44A	124.4
C17—C16—H16A	120.9	N7—C44—H44A	124.4
C16—C17—C12	122.1 (2)	O3—C45—C42	120.0 (2)
C16—C17—H17A	119.0	O3—C45—C46	120.1 (2)
C12—C17—H17A	119.0	C42—C45—C46	119.76 (19)
C19—C18—C23	120.5 (2)	C47—C46—C51	117.0 (2)
C19—C18—Cl2	119.1 (2)	C47—C46—C45	124.74 (19)
C23—C18—Cl2	120.4 (2)	C51—C46—C45	118.3 (2)
C20—C19—C18	119.7 (2)	F6—C47—C46	119.30 (19)
C20—C19—H19A	120.1	F6—C47—C48	116.8 (2)
C18—C19—H19A	120.1	C46—C47—C48	123.9 (2)
C19—C20—C21	120.8 (2)	C47—C48—C49	115.8 (2)
C19—C20—H20A	119.6	C47—C48—H48A	122.1
C21—C20—H20A	119.6	C49—C48—H48A	122.1
C20—C21—C22	118.1 (2)	F5—C49—C50	119.0 (2)
C20—C21—C24	123.7 (2)	F5—C49—C48	117.0 (2)
C22—C21—C24	118.1 (2)	C50—C49—C48	124.0 (2)
C23—C22—C21	120.9 (2)	C49—C50—C51	118.0 (2)
C23—C22—H22A	119.5	C49—C50—H50A	121.0
C21—C22—H22A	119.5	C51—C50—H50A	121.0
C22—C23—C18	119.9 (2)	C46—C51—C50	121.3 (2)
C22—C23—H23A	120.1	C46—C51—H51A	119.3
C18—C23—H23A	120.1	C50—C51—H51A	119.3
C27—C24—C21	129.9 (2)	C10—N1—N2	108.76 (19)
C27—C24—H24A	115.0	C10—N1—C8	130.4 (2)
C21—C24—H24A	115.0	N2—N1—C8	120.77 (16)
N5—C25—N6	115.8 (2)	C9—N2—N1	102.15 (18)
N5—C25—H25A	122.1	C10—N3—C9	102.13 (19)
N6—C25—H25A	122.1	C26—N4—N5	108.30 (18)
N6—C26—N4	111.7 (2)	C26—N4—C27	128.79 (19)
N6—C26—H26A	124.1	N5—N4—C27	122.78 (17)
N4—C26—H26A	124.1	C25—N5—N4	102.26 (19)
C24—C27—N4	122.06 (19)	C26—N6—C25	101.9 (2)
C24—C27—C28	122.56 (19)	C44—N7—N8	108.84 (19)
N4—C27—C28	114.39 (18)	C44—N7—C42	131.2 (2)
O2—C28—C29	120.7 (2)	N8—N7—C42	119.98 (16)
O2—C28—C27	119.6 (2)	C43—N8—N7	101.92 (19)
C29—C28—C27	119.55 (19)	C44—N9—C43	102.13 (19)

C6—C1—C2—C3	−0.4 (5)	C28—C29—C34—C33	179.8 (2)
Cl1—C1—C2—C3	179.5 (2)	C40—C35—C36—C37	0.4 (4)
C1—C2—C3—C4	−0.3 (4)	Cl3—C35—C36—C37	−179.2 (2)
C2—C3—C4—C5	1.2 (4)	C35—C36—C37—C38	0.2 (4)
C2—C3—C4—C7	178.6 (2)	C36—C37—C38—C39	0.0 (4)
C3—C4—C5—C6	−1.4 (4)	C36—C37—C38—C41	175.4 (2)
C7—C4—C5—C6	−178.6 (3)	C37—C38—C39—C40	−0.8 (4)
C2—C1—C6—C5	0.2 (5)	C41—C38—C39—C40	−176.3 (2)
Cl1—C1—C6—C5	−179.7 (2)	C36—C35—C40—C39	−1.1 (4)
C4—C5—C6—C1	0.8 (5)	Cl3—C35—C40—C39	178.5 (2)
C5—C4—C7—C8	−5.3 (4)	C38—C39—C40—C35	1.3 (4)
C3—C4—C7—C8	177.5 (2)	C39—C38—C41—C42	−157.0 (3)
C4—C7—C8—N1	−4.1 (4)	C37—C38—C41—C42	27.8 (4)
C4—C7—C8—C11	169.3 (2)	C38—C41—C42—N7	7.8 (4)
C7—C8—C11—O1	−148.9 (2)	C38—C41—C42—C45	−165.9 (2)
N1—C8—C11—O1	25.1 (3)	C41—C42—C45—O3	150.1 (2)
C7—C8—C11—C12	27.3 (3)	N7—C42—C45—O3	−24.0 (3)
N1—C8—C11—C12	−158.77 (18)	C41—C42—C45—C46	−25.4 (3)
O1—C11—C12—C13	−135.5 (2)	N7—C42—C45—C46	160.52 (18)
C8—C11—C12—C13	48.3 (3)	O3—C45—C46—C47	137.4 (2)
O1—C11—C12—C17	41.3 (3)	C42—C45—C46—C47	−47.1 (3)
C8—C11—C12—C17	−134.8 (2)	O3—C45—C46—C51	−39.7 (3)
C17—C12—C13—F1	−179.06 (19)	C42—C45—C46—C51	135.8 (2)
C11—C12—C13—F1	−2.1 (3)	C51—C46—C47—F6	177.1 (2)
C17—C12—C13—C14	0.1 (3)	C45—C46—C47—F6	0.0 (3)
C11—C12—C13—C14	177.0 (2)	C51—C46—C47—C48	−1.1 (3)
F1—C13—C14—C15	−179.8 (2)	C45—C46—C47—C48	−178.2 (2)
C12—C13—C14—C15	1.0 (3)	F6—C47—C48—C49	−178.9 (2)
C13—C14—C15—F2	178.9 (2)	C46—C47—C48—C49	−0.6 (3)
C13—C14—C15—C16	−0.6 (4)	C47—C48—C49—F5	−178.9 (2)
F2—C15—C16—C17	179.5 (2)	C47—C48—C49—C50	1.4 (4)
C14—C15—C16—C17	−1.0 (4)	F5—C49—C50—C51	179.8 (2)
C15—C16—C17—C12	2.3 (4)	C48—C49—C50—C51	−0.5 (4)
C13—C12—C17—C16	−1.8 (3)	C47—C46—C51—C50	2.1 (3)
C11—C12—C17—C16	−178.9 (2)	C45—C46—C51—C50	179.4 (2)
C23—C18—C19—C20	2.8 (4)	C49—C50—C51—C46	−1.4 (4)
Cl2—C18—C19—C20	−178.9 (2)	N3—C10—N1—N2	1.5 (3)
C18—C19—C20—C21	−1.1 (4)	N3—C10—N1—C8	177.9 (2)
C19—C20—C21—C22	−2.1 (4)	C7—C8—N1—C10	112.1 (3)
C19—C20—C21—C24	−180.0 (2)	C11—C8—N1—C10	−61.8 (3)
C20—C21—C22—C23	3.7 (4)	C7—C8—N1—N2	−71.9 (3)
C24—C21—C22—C23	−178.4 (2)	C11—C8—N1—N2	114.2 (2)
C21—C22—C23—C18	−2.0 (4)	N3—C9—N2—N1	0.4 (3)
C19—C18—C23—C22	−1.3 (4)	C10—N1—N2—C9	−1.1 (3)
Cl2—C18—C23—C22	−179.6 (2)	C8—N1—N2—C9	−177.9 (2)
C20—C21—C24—C27	−34.9 (4)	N1—C10—N3—C9	−1.2 (3)
C22—C21—C24—C27	147.3 (3)	N2—C9—N3—C10	0.4 (3)
C21—C24—C27—N4	−2.8 (4)	N6—C26—N4—N5	−1.2 (3)
C21—C24—C27—C28	−170.8 (2)	N6—C26—N4—C27	−177.1 (2)
C24—C27—C28—O2	150.8 (2)	C24—C27—N4—C26	−95.4 (3)
N4—C27—C28—O2	−18.0 (3)	C28—C27—N4—C26	73.4 (3)
C24—C27—C28—C29	−25.0 (3)	C24—C27—N4—N5	89.2 (3)
N4—C27—C28—C29	166.23 (18)	C28—C27—N4—N5	−101.9 (2)
O2—C28—C29—C30	−42.7 (3)	N6—C25—N5—N4	−0.8 (3)
C27—C28—C29—C30	133.0 (2)	C26—N4—N5—C25	1.1 (3)
O2—C28—C29—C34	136.6 (2)	C27—N4—N5—C25	177.3 (2)
C27—C28—C29—C34	−47.7 (3)	N4—C26—N6—C25	0.7 (4)
C34—C29—C30—C31	1.9 (3)	N5—C25—N6—C26	0.1 (4)
C28—C29—C30—C31	−178.8 (2)	N9—C44—N7—N8	−0.6 (3)
C29—C30—C31—C32	−1.3 (4)	N9—C44—N7—C42	179.4 (2)
C30—C31—C32—F4	179.5 (2)	C41—C42—N7—C44	−123.7 (3)
C30—C31—C32—C33	−0.4 (4)	C45—C42—N7—C44	50.4 (3)
C31—C32—C33—C34	1.4 (4)	C41—C42—N7—N8	56.2 (3)
F4—C32—C33—C34	−178.5 (2)	C45—C42—N7—N8	−129.6 (2)
C32—C33—C34—F3	−179.4 (2)	N9—C43—N8—N7	0.4 (3)
C32—C33—C34—C29	−0.7 (4)	C44—N7—N8—C43	0.1 (2)
C30—C29—C34—F3	177.8 (2)	C42—N7—N8—C43	−179.89 (19)
C28—C29—C34—F3	−1.5 (3)	N7—C44—N9—C43	0.7 (3)
C30—C29—C34—C33	−0.8 (3)	N8—C43—N9—C44	−0.7 (3)

Experimental details

Crystal data
Chemical formula	C₁₇H₁₀ClF₂N₃O
M_r	345.73
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	17.237 (3), 10.466 (2), 26.554 (5)
β (°)	102.378 (4)
V (Å³)	4679.2 (16)
Z	12
Radiation type	Mo Kα
µ (mm⁻¹)	0.28
Crystal size (mm)	0.23 × 0.21 × 0.17

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.939, 0.955
No. of measured, independent and observed [I > 2σ(I)] reflections	25352, 9200, 5656
R_int	0.032
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.133, 1.01
No. of reflections	9200
No. of parameters	650
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.34, −0.35

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009), SHELXTL (Sheldrick, 2008).

Acknowledgements

This work was partially supported by the National Natural Science Foundation of China (No. 21172181), the key program of the Natural Science Foundation of Chongqing (CSTC2012jjB10026), the Specialized Research Fund for the Doctoral Program of Higher Education of China (SRFDP 20110182110007) and the Research Funds for the Central Universities (XDJK2011D007, XDJK2012B026).

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