organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

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

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[Bai, X., Zhou, C.-H. & Mi, J.-L. (2007). Chem. Res. Appl. 19, 721-729.]); Chang et al. (2011[Chang, J.-J., Wang, Y., Zhang, H.-Z., Zhou, C.-H., Geng, R.-X. & Ji, Q.-G. (2011). Chem. J. Chin. Univ. 32, 1970-1985.]); Wang & Zhou (2011[Wang, Y. & Zhou, C.-H. (2011). Sci. Sin. Chim. 41, 1429-1456.]); Zhou & Wang (2012[Zhou, C.-H. & Wang, Y. (2012). Curr. Med. Chem. 19, 239-280.]). For the pharmacological activity of chalcones, see: Jin et al. (2010[Jin, L., Yan, C.-Y., Gan, L.-L. & Zhou, C.-H. (2010). Chin. J. Biochem. Pharm. 31, 358-361.]). For the synthesis of the title compound, see: Yan et al. (2009[Yan, C.-Y., Wang, G.-Z. & Zhou, C.-H. (2009). Acta Cryst. E65, o2054.]). For related structures, see: Wang et al. (2009[Wang, G., Lu, Y., Zhou, C. & Zhang, Y. (2009). Acta Cryst. E65, o1113.]); Yan et al. (2009[Yan, C.-Y., Wang, G.-Z. & Zhou, C.-H. (2009). Acta Cryst. E65, o2054.]).

[Scheme 1]

Experimental

Crystal data
  • C17H10ClF2N3O

  • Mr = 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[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.939, Tmax = 0.955

  • 25352 measured reflections

  • 9200 independent reflections

  • 5656 reflections with I > 2σ(I)

  • Rint = 0.032

Refinement
  • R[F2 > 2σ(F2)] = 0.045

  • wR(F2) = 0.133

  • S = 1.01

  • 9200 reflections

  • 650 parameters

  • H-atom parameters constrained

  • Δρmax = 0.34 e Å−3

  • Δρmin = −0.35 e Å−3

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]).

Supporting information


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 CC 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.

Refinement top

H atoms were placed in calculated positions with C—H = 0.93 Å. The Uiso(H) value was set equal to 1.2Ueq(C).

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
[Figure 1] 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
C17H10ClF2N3OF(000) = 2112
Mr = 345.73Dx = 1.472 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 5332 reflections
a = 17.237 (3) Åθ = 2.2–22.9°
b = 10.466 (2) ŵ = 0.28 mm1
c = 26.554 (5) ÅT = 296 K
β = 102.378 (4)°Block, colorless
V = 4679.2 (16) Å30.23 × 0.21 × 0.17 mm
Z = 12
Data collection top
Bruker APEXII CCD
diffractometer
9200 independent reflections
Radiation source: fine-focus sealed tube5656 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.032
ϕ and ω scansθmax = 26.0°, θmin = 1.6°
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
h = 2021
Tmin = 0.939, Tmax = 0.955k = 1210
25352 measured reflectionsl = 3230
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.045H-atom parameters constrained
wR(F2) = 0.133 w = 1/[σ2(Fo2) + (0.0626P)2 + 0.7017P]
where P = (Fo2 + 2Fc2)/3
S = 1.01(Δ/σ)max = 0.001
9200 reflectionsΔρmax = 0.34 e Å3
650 parametersΔρmin = 0.35 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0015 (2)
Crystal data top
C17H10ClF2N3OV = 4679.2 (16) Å3
Mr = 345.73Z = 12
Monoclinic, P21/cMo Kα radiation
a = 17.237 (3) ŵ = 0.28 mm1
b = 10.466 (2) ÅT = 296 K
c = 26.554 (5) Å0.23 × 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)
Tmin = 0.939, Tmax = 0.955Rint = 0.032
25352 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0450 restraints
wR(F2) = 0.133H-atom parameters constrained
S = 1.01Δρmax = 0.34 e Å3
9200 reflectionsΔρmin = 0.35 e Å3
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
xyzUiso*/Ueq
F10.20468 (8)0.35283 (12)0.14981 (5)0.0668 (4)
F20.05967 (9)0.66430 (13)0.21328 (7)0.0874 (5)
F30.78892 (9)0.56839 (13)0.52214 (5)0.0708 (4)
F40.92930 (10)0.25782 (15)0.45456 (8)0.1080 (6)
F50.92861 (9)0.25932 (13)0.09951 (7)0.0901 (5)
F60.80518 (9)0.56279 (12)0.18279 (5)0.0717 (4)
C10.52331 (16)0.0907 (3)0.29462 (11)0.0747 (7)
C20.49247 (17)0.2060 (3)0.30181 (12)0.0815 (8)
H2A0.52430.26940.32020.098*
C30.41327 (15)0.2288 (2)0.28162 (10)0.0694 (7)
H3A0.39220.30830.28680.083*
C40.36428 (13)0.1379 (2)0.25404 (8)0.0509 (5)
C50.39820 (17)0.0207 (2)0.24830 (11)0.0806 (8)
H5A0.36680.04410.23060.097*
C60.47705 (18)0.0022 (3)0.26816 (13)0.0909 (9)
H6A0.49880.08150.26350.109*
C70.28127 (13)0.1712 (2)0.23551 (8)0.0506 (5)
H7A0.26780.25200.24540.061*
C80.22060 (13)0.10637 (19)0.20677 (8)0.0474 (5)
C90.26059 (15)0.1494 (2)0.13538 (10)0.0628 (7)
H9A0.28120.18700.10930.075*
C100.20371 (17)0.1289 (2)0.19568 (12)0.0769 (8)
H10A0.17550.14420.22130.092*
C110.13747 (13)0.1504 (2)0.19983 (8)0.0492 (5)
C120.11973 (12)0.2886 (2)0.20359 (8)0.0460 (5)
C130.15149 (13)0.3843 (2)0.17871 (8)0.0480 (5)
C140.13213 (14)0.5102 (2)0.18068 (9)0.0560 (6)
H14A0.15410.57230.16290.067*
C150.07866 (14)0.5404 (2)0.21011 (10)0.0604 (6)
C160.04492 (14)0.4512 (2)0.23620 (10)0.0637 (7)
H16A0.00930.47500.25630.076*
C170.06485 (13)0.3261 (2)0.23190 (9)0.0566 (6)
H17A0.04080.26410.24850.068*
C180.45770 (14)0.8091 (3)0.38261 (11)0.0663 (7)
C190.49635 (14)0.8600 (2)0.42844 (11)0.0712 (7)
H19A0.46880.90980.44780.085*
C200.57613 (14)0.8375 (2)0.44587 (10)0.0660 (7)
H20A0.60260.87350.47680.079*
C210.61753 (12)0.76197 (19)0.41791 (9)0.0496 (5)
C220.57591 (14)0.7066 (2)0.37302 (10)0.0659 (7)
H22A0.60190.65160.35470.079*
C230.49680 (15)0.7317 (3)0.35512 (11)0.0761 (8)
H23A0.46980.69590.32420.091*
C240.70225 (12)0.7339 (2)0.43406 (8)0.0491 (5)
H24A0.71710.65260.42560.059*
C250.72815 (15)1.0924 (2)0.51513 (10)0.0626 (6)
H25A0.71571.14250.54120.075*
C260.75847 (19)1.0413 (2)0.44775 (11)0.0860 (9)
H26A0.77281.04340.41590.103*
C270.76129 (12)0.80666 (19)0.45894 (8)0.0454 (5)
C280.84596 (13)0.7695 (2)0.46558 (8)0.0495 (5)
C290.86721 (12)0.6328 (2)0.46420 (8)0.0478 (5)
C300.92034 (13)0.5955 (2)0.43433 (10)0.0598 (6)
H30A0.94220.65730.41640.072*
C310.94140 (15)0.4701 (3)0.43059 (11)0.0717 (7)
H31A0.97620.44630.40990.086*
C320.91002 (15)0.3813 (2)0.45796 (11)0.0697 (7)
C330.85911 (14)0.4115 (2)0.48906 (10)0.0621 (6)
H33A0.83930.34940.50800.075*
C340.83867 (12)0.5369 (2)0.49113 (9)0.0507 (5)
C350.48083 (14)0.8658 (3)0.05895 (10)0.0672 (7)
C360.53758 (16)0.9580 (3)0.06771 (10)0.0712 (7)
H36A0.52321.04340.06230.085*
C370.61618 (15)0.9259 (2)0.08456 (10)0.0654 (7)
H37A0.65450.98990.09050.078*
C380.63907 (13)0.8001 (2)0.09278 (9)0.0535 (6)
C390.58004 (16)0.7084 (3)0.08339 (11)0.0749 (8)
H39A0.59400.62270.08820.090*
C400.50156 (16)0.7403 (3)0.06715 (12)0.0795 (8)
H40A0.46270.67710.06180.095*
C410.72159 (13)0.7588 (2)0.10696 (9)0.0537 (6)
H41A0.73060.67630.09650.064*
C420.78625 (13)0.81873 (19)0.13225 (8)0.0486 (5)
C430.74745 (15)1.0733 (2)0.20480 (10)0.0635 (7)
H43A0.72351.11140.22920.076*
C440.81640 (15)1.0507 (2)0.15076 (10)0.0627 (7)
H44A0.85071.06440.12860.075*
C450.86757 (14)0.7726 (2)0.13301 (9)0.0529 (6)
C460.88146 (12)0.6337 (2)0.12470 (8)0.0470 (5)
C470.85120 (13)0.5356 (2)0.14879 (8)0.0507 (5)
C480.86624 (13)0.4091 (2)0.14169 (9)0.0555 (6)
H48A0.84530.34440.15880.067*
C490.91392 (14)0.3839 (2)0.10796 (10)0.0605 (6)
C500.94698 (14)0.4753 (3)0.08309 (10)0.0646 (7)
H50A0.97950.45360.06060.078*
C510.93108 (13)0.6008 (2)0.09209 (9)0.0579 (6)
H51A0.95410.66500.07600.069*
Cl10.62306 (5)0.05800 (11)0.31895 (4)0.1276 (4)
Cl20.35746 (4)0.84070 (10)0.36066 (4)0.1091 (3)
Cl30.38200 (4)0.90807 (9)0.03691 (4)0.0978 (3)
N10.22974 (11)0.01526 (15)0.18508 (7)0.0500 (5)
N20.26661 (11)0.02714 (17)0.14488 (7)0.0547 (5)
N30.22279 (14)0.21717 (19)0.16551 (10)0.0817 (7)
N40.74910 (10)0.93572 (15)0.47265 (7)0.0467 (4)
N50.72995 (12)0.96812 (17)0.51768 (7)0.0587 (5)
N60.74517 (17)1.1429 (2)0.47318 (11)0.0942 (8)
N70.78198 (11)0.93912 (15)0.15638 (7)0.0489 (4)
N80.73630 (11)0.95284 (17)0.19205 (7)0.0548 (5)
N90.79562 (13)1.13848 (18)0.18044 (9)0.0696 (6)
O10.08400 (10)0.07287 (15)0.19375 (7)0.0703 (5)
O20.89650 (9)0.85179 (15)0.46908 (7)0.0690 (5)
O30.92184 (10)0.84789 (16)0.13720 (7)0.0728 (5)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
F10.0852 (10)0.0554 (8)0.0731 (9)0.0047 (7)0.0466 (8)0.0060 (7)
F20.0891 (11)0.0574 (9)0.1196 (14)0.0236 (8)0.0306 (10)0.0069 (8)
F30.0855 (10)0.0639 (9)0.0737 (9)0.0103 (7)0.0411 (8)0.0058 (7)
F40.1029 (13)0.0660 (10)0.1600 (18)0.0361 (9)0.0389 (12)0.0070 (10)
F50.0972 (12)0.0578 (9)0.1217 (14)0.0124 (8)0.0375 (10)0.0182 (9)
F60.0993 (11)0.0597 (8)0.0698 (9)0.0010 (7)0.0486 (8)0.0020 (7)
C10.0620 (17)0.089 (2)0.0703 (18)0.0014 (16)0.0085 (14)0.0089 (16)
C20.0697 (19)0.079 (2)0.093 (2)0.0155 (16)0.0105 (16)0.0116 (16)
C30.0668 (17)0.0624 (16)0.0796 (19)0.0030 (13)0.0170 (14)0.0114 (13)
C40.0609 (14)0.0462 (13)0.0474 (13)0.0010 (11)0.0155 (11)0.0011 (10)
C50.0762 (19)0.0583 (16)0.095 (2)0.0095 (14)0.0097 (16)0.0104 (15)
C60.080 (2)0.0715 (19)0.109 (2)0.0242 (16)0.0054 (18)0.0060 (17)
C70.0635 (15)0.0403 (12)0.0516 (13)0.0008 (11)0.0203 (11)0.0007 (10)
C80.0603 (14)0.0358 (11)0.0504 (13)0.0037 (10)0.0213 (11)0.0001 (9)
C90.0751 (17)0.0405 (13)0.0768 (17)0.0004 (12)0.0248 (14)0.0078 (12)
C100.098 (2)0.0397 (14)0.108 (2)0.0073 (13)0.0561 (18)0.0052 (14)
C110.0546 (13)0.0476 (13)0.0498 (13)0.0083 (11)0.0211 (11)0.0019 (10)
C120.0453 (12)0.0454 (12)0.0489 (13)0.0030 (10)0.0136 (10)0.0028 (10)
C130.0509 (13)0.0481 (13)0.0488 (13)0.0009 (10)0.0191 (11)0.0019 (10)
C140.0609 (15)0.0461 (13)0.0628 (15)0.0013 (11)0.0169 (12)0.0022 (11)
C150.0559 (15)0.0523 (15)0.0716 (16)0.0128 (12)0.0104 (13)0.0089 (12)
C160.0534 (14)0.0699 (17)0.0732 (17)0.0086 (12)0.0251 (13)0.0118 (13)
C170.0502 (13)0.0612 (15)0.0630 (15)0.0028 (11)0.0221 (12)0.0025 (11)
C180.0450 (13)0.0761 (17)0.0757 (18)0.0005 (12)0.0081 (13)0.0074 (14)
C190.0517 (15)0.0742 (17)0.088 (2)0.0079 (13)0.0147 (14)0.0202 (15)
C200.0500 (14)0.0764 (17)0.0701 (17)0.0039 (13)0.0099 (12)0.0214 (13)
C210.0471 (13)0.0438 (12)0.0575 (14)0.0006 (10)0.0107 (11)0.0043 (10)
C220.0574 (15)0.0715 (16)0.0687 (17)0.0019 (13)0.0131 (13)0.0196 (13)
C230.0577 (16)0.096 (2)0.0688 (18)0.0033 (15)0.0013 (13)0.0230 (15)
C240.0492 (13)0.0443 (12)0.0545 (14)0.0041 (10)0.0131 (11)0.0022 (10)
C250.0736 (17)0.0462 (15)0.0695 (17)0.0032 (12)0.0188 (14)0.0100 (12)
C260.139 (3)0.0516 (16)0.085 (2)0.0185 (16)0.062 (2)0.0197 (15)
C270.0529 (13)0.0390 (12)0.0460 (12)0.0029 (10)0.0141 (10)0.0009 (9)
C280.0470 (13)0.0525 (13)0.0493 (13)0.0041 (11)0.0110 (10)0.0030 (10)
C290.0383 (11)0.0519 (13)0.0518 (13)0.0040 (10)0.0065 (10)0.0028 (10)
C300.0436 (13)0.0695 (16)0.0689 (16)0.0039 (12)0.0178 (12)0.0007 (12)
C310.0531 (15)0.0789 (19)0.086 (2)0.0196 (14)0.0214 (14)0.0113 (16)
C320.0599 (16)0.0566 (16)0.090 (2)0.0202 (13)0.0109 (15)0.0109 (14)
C330.0591 (15)0.0538 (15)0.0720 (17)0.0072 (12)0.0107 (13)0.0035 (12)
C340.0461 (13)0.0543 (14)0.0530 (13)0.0073 (10)0.0133 (11)0.0021 (11)
C350.0549 (15)0.0831 (19)0.0667 (17)0.0069 (14)0.0197 (13)0.0031 (14)
C360.0665 (17)0.0618 (16)0.0816 (19)0.0002 (14)0.0075 (14)0.0038 (14)
C370.0626 (16)0.0576 (15)0.0721 (17)0.0108 (12)0.0059 (13)0.0026 (12)
C380.0561 (14)0.0512 (14)0.0550 (14)0.0074 (11)0.0160 (11)0.0104 (11)
C390.0683 (18)0.0578 (15)0.097 (2)0.0115 (13)0.0143 (15)0.0122 (14)
C400.0622 (18)0.077 (2)0.100 (2)0.0216 (15)0.0173 (16)0.0139 (16)
C410.0628 (15)0.0460 (13)0.0543 (14)0.0061 (11)0.0173 (12)0.0040 (10)
C420.0592 (14)0.0384 (12)0.0502 (13)0.0063 (10)0.0165 (11)0.0016 (10)
C430.0783 (18)0.0427 (14)0.0684 (16)0.0042 (12)0.0133 (14)0.0033 (12)
C440.0692 (16)0.0396 (13)0.0810 (18)0.0086 (12)0.0201 (14)0.0077 (12)
C450.0592 (15)0.0503 (13)0.0510 (14)0.0097 (11)0.0159 (11)0.0015 (10)
C460.0475 (12)0.0463 (12)0.0478 (12)0.0021 (10)0.0117 (10)0.0003 (10)
C470.0555 (14)0.0523 (14)0.0467 (13)0.0020 (11)0.0164 (11)0.0036 (10)
C480.0587 (14)0.0469 (13)0.0605 (15)0.0021 (11)0.0123 (12)0.0019 (11)
C490.0589 (15)0.0497 (14)0.0719 (17)0.0040 (12)0.0117 (13)0.0118 (12)
C500.0548 (15)0.0729 (18)0.0718 (17)0.0045 (13)0.0260 (13)0.0102 (14)
C510.0512 (14)0.0644 (16)0.0603 (15)0.0047 (12)0.0167 (12)0.0004 (12)
Cl10.0659 (5)0.1549 (9)0.1484 (9)0.0093 (5)0.0074 (5)0.0063 (7)
Cl20.0478 (4)0.1542 (8)0.1166 (7)0.0082 (5)0.0016 (4)0.0248 (6)
Cl30.0559 (4)0.1225 (7)0.1150 (7)0.0003 (4)0.0183 (4)0.0045 (5)
N10.0602 (12)0.0345 (10)0.0607 (12)0.0031 (8)0.0250 (10)0.0001 (8)
N20.0673 (13)0.0431 (11)0.0587 (12)0.0010 (9)0.0246 (10)0.0015 (9)
N30.0952 (17)0.0379 (11)0.126 (2)0.0095 (11)0.0542 (16)0.0073 (12)
N40.0548 (11)0.0395 (10)0.0483 (11)0.0019 (8)0.0165 (9)0.0025 (8)
N50.0820 (14)0.0457 (12)0.0506 (12)0.0018 (10)0.0192 (10)0.0016 (9)
N60.143 (2)0.0438 (13)0.114 (2)0.0119 (13)0.0683 (19)0.0111 (13)
N70.0567 (11)0.0364 (10)0.0544 (11)0.0046 (8)0.0138 (9)0.0038 (8)
N80.0693 (13)0.0418 (11)0.0559 (12)0.0011 (9)0.0193 (10)0.0016 (9)
N90.0769 (15)0.0384 (11)0.0924 (16)0.0040 (10)0.0157 (13)0.0009 (11)
O10.0655 (11)0.0531 (10)0.0987 (14)0.0161 (9)0.0317 (10)0.0087 (9)
O20.0545 (10)0.0589 (10)0.0935 (13)0.0102 (8)0.0158 (9)0.0070 (9)
O30.0633 (11)0.0564 (10)0.1024 (14)0.0139 (9)0.0257 (10)0.0045 (9)
Geometric parameters (Å, º) top
F1—C131.356 (2)C25—N61.321 (3)
F2—C151.345 (3)C25—H25A0.9300
F3—C341.351 (2)C26—N61.306 (3)
F4—C321.343 (3)C26—N41.315 (3)
F5—C491.356 (3)C26—H26A0.9300
F6—C471.354 (2)C27—N41.426 (3)
C1—C61.354 (4)C27—C281.484 (3)
C1—C21.349 (4)C28—O21.214 (2)
C1—Cl11.736 (3)C28—C291.479 (3)
C2—C31.376 (4)C29—C301.390 (3)
C2—H2A0.9300C29—C341.383 (3)
C3—C41.374 (3)C30—C311.371 (3)
C3—H3A0.9300C30—H30A0.9300
C4—C51.382 (3)C31—C321.361 (4)
C4—C71.452 (3)C31—H31A0.9300
C5—C61.369 (4)C32—C331.365 (3)
C5—H5A0.9300C33—C341.363 (3)
C6—H6A0.9300C33—H33A0.9300
C7—C81.339 (3)C35—C361.358 (3)
C7—H7A0.9300C35—C401.367 (4)
C8—N11.420 (3)C35—Cl31.736 (3)
C8—C111.479 (3)C36—C371.374 (3)
C9—N21.304 (3)C36—H36A0.9300
C9—N31.339 (3)C37—C381.378 (3)
C9—H9A0.9300C37—H37A0.9300
C10—N31.310 (3)C38—C391.382 (3)
C10—N11.323 (3)C38—C411.457 (3)
C10—H10A0.9300C39—C401.370 (4)
C11—O11.212 (2)C39—H39A0.9300
C11—C121.486 (3)C40—H40A0.9300
C12—C131.376 (3)C41—C421.329 (3)
C12—C171.385 (3)C41—H41A0.9300
C13—C141.363 (3)C42—N71.423 (3)
C14—C151.367 (3)C42—C451.479 (3)
C14—H14A0.9300C43—N81.308 (3)
C15—C161.364 (3)C43—N91.343 (3)
C16—C171.365 (3)C43—H43A0.9300
C16—H16A0.9300C44—N91.310 (3)
C17—H17A0.9300C44—N71.332 (3)
C18—C191.365 (3)C44—H44A0.9300
C18—C231.362 (3)C45—O31.210 (3)
C18—Cl21.733 (2)C45—C461.497 (3)
C19—C201.374 (3)C46—C471.371 (3)
C19—H19A0.9300C46—C511.385 (3)
C20—C211.383 (3)C47—C481.370 (3)
C20—H20A0.9300C48—C491.365 (3)
C21—C221.380 (3)C48—H48A0.9300
C21—C241.461 (3)C49—C501.356 (3)
C22—C231.370 (3)C50—C511.373 (3)
C22—H22A0.9300C50—H50A0.9300
C23—H23A0.9300C51—H51A0.9300
C24—C271.328 (3)N1—N21.360 (2)
C24—H24A0.9300N4—N51.350 (2)
C25—N51.303 (3)N7—N81.363 (2)
C6—C1—C2120.6 (3)C30—C29—C34116.2 (2)
C6—C1—Cl1118.5 (2)C30—C29—C28118.9 (2)
C2—C1—Cl1120.8 (2)C34—C29—C28124.89 (19)
C3—C2—C1119.2 (3)C29—C30—C31121.8 (2)
C3—C2—H2A120.4C29—C30—H30A119.1
C1—C2—H2A120.4C31—C30—H30A119.1
C2—C3—C4122.2 (3)C32—C31—C30118.2 (2)
C2—C3—H3A118.9C32—C31—H31A120.9
C4—C3—H3A118.9C30—C31—H31A120.9
C5—C4—C3116.6 (2)C31—C32—F4119.3 (2)
C5—C4—C7125.8 (2)C31—C32—C33123.1 (2)
C3—C4—C7117.6 (2)F4—C32—C33117.6 (3)
C4—C5—C6121.4 (3)C32—C33—C34116.9 (2)
C4—C5—H5A119.3C32—C33—H33A121.6
C6—C5—H5A119.3C34—C33—H33A121.6
C1—C6—C5120.0 (3)F3—C34—C33117.6 (2)
C1—C6—H6A120.0F3—C34—C29118.71 (19)
C5—C6—H6A120.0C33—C34—C29123.7 (2)
C8—C7—C4131.6 (2)C36—C35—C40120.1 (3)
C8—C7—H7A114.2C36—C35—Cl3119.7 (2)
C4—C7—H7A114.2C40—C35—Cl3120.2 (2)
C7—C8—N1123.0 (2)C35—C36—C37120.3 (2)
C7—C8—C11122.05 (19)C35—C36—H36A119.8
N1—C8—C11114.69 (19)C37—C36—H36A119.8
N2—C9—N3115.7 (2)C36—C37—C38120.9 (2)
N2—C9—H9A122.2C36—C37—H37A119.5
N3—C9—H9A122.2C38—C37—H37A119.5
N3—C10—N1111.3 (2)C39—C38—C37117.4 (2)
N3—C10—H10A124.4C39—C38—C41118.7 (2)
N1—C10—H10A124.4C37—C38—C41123.7 (2)
O1—C11—C8119.8 (2)C40—C39—C38121.8 (3)
O1—C11—C12119.9 (2)C40—C39—H39A119.1
C8—C11—C12120.18 (18)C38—C39—H39A119.1
C13—C12—C17116.3 (2)C35—C40—C39119.4 (2)
C13—C12—C11124.56 (18)C35—C40—H40A120.3
C17—C12—C11119.10 (19)C39—C40—H40A120.3
F1—C13—C14117.20 (19)C42—C41—C38131.1 (2)
F1—C13—C12118.81 (18)C42—C41—H41A114.4
C14—C13—C12124.0 (2)C38—C41—H41A114.4
C15—C14—C13116.5 (2)C41—C42—N7121.8 (2)
C15—C14—H14A121.8C41—C42—C45122.9 (2)
C13—C14—H14A121.8N7—C42—C45115.06 (19)
F2—C15—C14117.5 (2)N8—C43—N9115.9 (2)
F2—C15—C16119.5 (2)N8—C43—H43A122.1
C14—C15—C16123.0 (2)N9—C43—H43A122.1
C15—C16—C17118.1 (2)N9—C44—N7111.2 (2)
C15—C16—H16A120.9N9—C44—H44A124.4
C17—C16—H16A120.9N7—C44—H44A124.4
C16—C17—C12122.1 (2)O3—C45—C42120.0 (2)
C16—C17—H17A119.0O3—C45—C46120.1 (2)
C12—C17—H17A119.0C42—C45—C46119.76 (19)
C19—C18—C23120.5 (2)C47—C46—C51117.0 (2)
C19—C18—Cl2119.1 (2)C47—C46—C45124.74 (19)
C23—C18—Cl2120.4 (2)C51—C46—C45118.3 (2)
C20—C19—C18119.7 (2)F6—C47—C46119.30 (19)
C20—C19—H19A120.1F6—C47—C48116.8 (2)
C18—C19—H19A120.1C46—C47—C48123.9 (2)
C19—C20—C21120.8 (2)C47—C48—C49115.8 (2)
C19—C20—H20A119.6C47—C48—H48A122.1
C21—C20—H20A119.6C49—C48—H48A122.1
C20—C21—C22118.1 (2)F5—C49—C50119.0 (2)
C20—C21—C24123.7 (2)F5—C49—C48117.0 (2)
C22—C21—C24118.1 (2)C50—C49—C48124.0 (2)
C23—C22—C21120.9 (2)C49—C50—C51118.0 (2)
C23—C22—H22A119.5C49—C50—H50A121.0
C21—C22—H22A119.5C51—C50—H50A121.0
C22—C23—C18119.9 (2)C46—C51—C50121.3 (2)
C22—C23—H23A120.1C46—C51—H51A119.3
C18—C23—H23A120.1C50—C51—H51A119.3
C27—C24—C21129.9 (2)C10—N1—N2108.76 (19)
C27—C24—H24A115.0C10—N1—C8130.4 (2)
C21—C24—H24A115.0N2—N1—C8120.77 (16)
N5—C25—N6115.8 (2)C9—N2—N1102.15 (18)
N5—C25—H25A122.1C10—N3—C9102.13 (19)
N6—C25—H25A122.1C26—N4—N5108.30 (18)
N6—C26—N4111.7 (2)C26—N4—C27128.79 (19)
N6—C26—H26A124.1N5—N4—C27122.78 (17)
N4—C26—H26A124.1C25—N5—N4102.26 (19)
C24—C27—N4122.06 (19)C26—N6—C25101.9 (2)
C24—C27—C28122.56 (19)C44—N7—N8108.84 (19)
N4—C27—C28114.39 (18)C44—N7—C42131.2 (2)
O2—C28—C29120.7 (2)N8—N7—C42119.98 (16)
O2—C28—C27119.6 (2)C43—N8—N7101.92 (19)
C29—C28—C27119.55 (19)C44—N9—C43102.13 (19)
C6—C1—C2—C30.4 (5)C28—C29—C34—C33179.8 (2)
Cl1—C1—C2—C3179.5 (2)C40—C35—C36—C370.4 (4)
C1—C2—C3—C40.3 (4)Cl3—C35—C36—C37179.2 (2)
C2—C3—C4—C51.2 (4)C35—C36—C37—C380.2 (4)
C2—C3—C4—C7178.6 (2)C36—C37—C38—C390.0 (4)
C3—C4—C5—C61.4 (4)C36—C37—C38—C41175.4 (2)
C7—C4—C5—C6178.6 (3)C37—C38—C39—C400.8 (4)
C2—C1—C6—C50.2 (5)C41—C38—C39—C40176.3 (2)
Cl1—C1—C6—C5179.7 (2)C36—C35—C40—C391.1 (4)
C4—C5—C6—C10.8 (5)Cl3—C35—C40—C39178.5 (2)
C5—C4—C7—C85.3 (4)C38—C39—C40—C351.3 (4)
C3—C4—C7—C8177.5 (2)C39—C38—C41—C42157.0 (3)
C4—C7—C8—N14.1 (4)C37—C38—C41—C4227.8 (4)
C4—C7—C8—C11169.3 (2)C38—C41—C42—N77.8 (4)
C7—C8—C11—O1148.9 (2)C38—C41—C42—C45165.9 (2)
N1—C8—C11—O125.1 (3)C41—C42—C45—O3150.1 (2)
C7—C8—C11—C1227.3 (3)N7—C42—C45—O324.0 (3)
N1—C8—C11—C12158.77 (18)C41—C42—C45—C4625.4 (3)
O1—C11—C12—C13135.5 (2)N7—C42—C45—C46160.52 (18)
C8—C11—C12—C1348.3 (3)O3—C45—C46—C47137.4 (2)
O1—C11—C12—C1741.3 (3)C42—C45—C46—C4747.1 (3)
C8—C11—C12—C17134.8 (2)O3—C45—C46—C5139.7 (3)
C17—C12—C13—F1179.06 (19)C42—C45—C46—C51135.8 (2)
C11—C12—C13—F12.1 (3)C51—C46—C47—F6177.1 (2)
C17—C12—C13—C140.1 (3)C45—C46—C47—F60.0 (3)
C11—C12—C13—C14177.0 (2)C51—C46—C47—C481.1 (3)
F1—C13—C14—C15179.8 (2)C45—C46—C47—C48178.2 (2)
C12—C13—C14—C151.0 (3)F6—C47—C48—C49178.9 (2)
C13—C14—C15—F2178.9 (2)C46—C47—C48—C490.6 (3)
C13—C14—C15—C160.6 (4)C47—C48—C49—F5178.9 (2)
F2—C15—C16—C17179.5 (2)C47—C48—C49—C501.4 (4)
C14—C15—C16—C171.0 (4)F5—C49—C50—C51179.8 (2)
C15—C16—C17—C122.3 (4)C48—C49—C50—C510.5 (4)
C13—C12—C17—C161.8 (3)C47—C46—C51—C502.1 (3)
C11—C12—C17—C16178.9 (2)C45—C46—C51—C50179.4 (2)
C23—C18—C19—C202.8 (4)C49—C50—C51—C461.4 (4)
Cl2—C18—C19—C20178.9 (2)N3—C10—N1—N21.5 (3)
C18—C19—C20—C211.1 (4)N3—C10—N1—C8177.9 (2)
C19—C20—C21—C222.1 (4)C7—C8—N1—C10112.1 (3)
C19—C20—C21—C24180.0 (2)C11—C8—N1—C1061.8 (3)
C20—C21—C22—C233.7 (4)C7—C8—N1—N271.9 (3)
C24—C21—C22—C23178.4 (2)C11—C8—N1—N2114.2 (2)
C21—C22—C23—C182.0 (4)N3—C9—N2—N10.4 (3)
C19—C18—C23—C221.3 (4)C10—N1—N2—C91.1 (3)
Cl2—C18—C23—C22179.6 (2)C8—N1—N2—C9177.9 (2)
C20—C21—C24—C2734.9 (4)N1—C10—N3—C91.2 (3)
C22—C21—C24—C27147.3 (3)N2—C9—N3—C100.4 (3)
C21—C24—C27—N42.8 (4)N6—C26—N4—N51.2 (3)
C21—C24—C27—C28170.8 (2)N6—C26—N4—C27177.1 (2)
C24—C27—C28—O2150.8 (2)C24—C27—N4—C2695.4 (3)
N4—C27—C28—O218.0 (3)C28—C27—N4—C2673.4 (3)
C24—C27—C28—C2925.0 (3)C24—C27—N4—N589.2 (3)
N4—C27—C28—C29166.23 (18)C28—C27—N4—N5101.9 (2)
O2—C28—C29—C3042.7 (3)N6—C25—N5—N40.8 (3)
C27—C28—C29—C30133.0 (2)C26—N4—N5—C251.1 (3)
O2—C28—C29—C34136.6 (2)C27—N4—N5—C25177.3 (2)
C27—C28—C29—C3447.7 (3)N4—C26—N6—C250.7 (4)
C34—C29—C30—C311.9 (3)N5—C25—N6—C260.1 (4)
C28—C29—C30—C31178.8 (2)N9—C44—N7—N80.6 (3)
C29—C30—C31—C321.3 (4)N9—C44—N7—C42179.4 (2)
C30—C31—C32—F4179.5 (2)C41—C42—N7—C44123.7 (3)
C30—C31—C32—C330.4 (4)C45—C42—N7—C4450.4 (3)
C31—C32—C33—C341.4 (4)C41—C42—N7—N856.2 (3)
F4—C32—C33—C34178.5 (2)C45—C42—N7—N8129.6 (2)
C32—C33—C34—F3179.4 (2)N9—C43—N8—N70.4 (3)
C32—C33—C34—C290.7 (4)C44—N7—N8—C430.1 (2)
C30—C29—C34—F3177.8 (2)C42—N7—N8—C43179.89 (19)
C28—C29—C34—F31.5 (3)N7—C44—N9—C430.7 (3)
C30—C29—C34—C330.8 (3)N8—C43—N9—C440.7 (3)

Experimental details

Crystal data
Chemical formulaC17H10ClF2N3O
Mr345.73
Crystal system, space groupMonoclinic, P21/c
Temperature (K)296
a, b, c (Å)17.237 (3), 10.466 (2), 26.554 (5)
β (°) 102.378 (4)
V3)4679.2 (16)
Z12
Radiation typeMo Kα
µ (mm1)0.28
Crystal size (mm)0.23 × 0.21 × 0.17
Data collection
DiffractometerBruker APEXII CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2009)
Tmin, Tmax0.939, 0.955
No. of measured, independent and
observed [I > 2σ(I)] reflections
25352, 9200, 5656
Rint0.032
(sin θ/λ)max1)0.617
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.045, 0.133, 1.01
No. of reflections9200
No. of parameters650
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)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).

References

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