(E)-1-(2,4-Dichloro-phen-yl)-3-(1,3-diphenyl-1H-pyrazol-4-yl)prop-2-en-1-one.

In the title mol-ecule, C(24)H(16)Cl(2)N(2)O, the dihedral angles between the pyrazole ring and its N- and C-bonded phenyl rings are 7.06 (10) and 53.15 (10)°, respectively. The dihedral angle between the two pendant rings is 52.32 (10)°. The mol-ecule exists in a trans conformation with respect to the acyclic C=C bond. In the crystal, inversion dimers occur in which each mol-ecule is linked to the other by two C-H⋯O hydrogen bonds to the same acceptor O atom. There are also short Cl⋯Cl contacts [3.3492 (9) Å] and C-H⋯π inter-actions.

Related literature

For general background to and the biological activity of pyrazoles, see: Patel et al. (2004 ▶); Isloor et al. (2009 ▶); Vijesh et al. (2010 ▶); Sharma et al. (2010 ▶); Rostom et al. (2003 ▶); Ghorab et al. (2010 ▶); Amnekar & Bhusari (2010 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For standard bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C24H16Cl2N2O

M = 419.29

Triclinic,

a = 9.6185 (8) Å

b = 10.6596 (9) Å

c = 11.8537 (10) Å

α = 67.377 (2)°

β = 75.777 (1)°

γ = 69.934 (2)°

V = 1044.64 (15) Å3

Z = 2

Mo Kα radiation

μ = 0.33 mm−1

T = 296 K

0.31 × 0.21 × 0.08 mm

Data collection

Bruker SMART APEXII DUO CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.904, T max = 0.973

22059 measured reflections

6053 independent reflections

3980 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.134

S = 1.04

6053 reflections

262 parameters

H-atom parameters constrained

Δρmax = 0.22 e Å−3

Δρmin = −0.27 e Å−3

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

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811044382/hb6456sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811044382/hb6456Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811044382/hb6456Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C24H16Cl2N2O	Z = 2
Mr = 419.29	F(000) = 432
Triclinic, P1	Dx = 1.333 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.6185 (8) Å	Cell parameters from 5364 reflections
b = 10.6596 (9) Å	θ = 2.4–28.8°
c = 11.8537 (10) Å	µ = 0.33 mm−1
α = 67.377 (2)°	T = 296 K
β = 75.777 (1)°	Block, colourless
γ = 69.934 (2)°	0.31 × 0.21 × 0.08 mm
V = 1044.64 (15) Å3

Bruker SMART APEXII DUO CCD diffractometer	6053 independent reflections
Radiation source: fine-focus sealed tube	3980 reflections with I > 2σ(I)
graphite	Rint = 0.027
φ and ω scans	θmax = 30.0°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −13→13
Tmin = 0.904, Tmax = 0.973	k = −14→14
22059 measured reflections	l = −16→16

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.134	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0581P)2 + 0.1623P] where P = (Fo2 + 2Fc2)/3
6053 reflections	(Δ/σ)max = 0.001
262 parameters	Δρmax = 0.22 e Å−3
0 restraints	Δρmin = −0.27 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	0.72422 (6)	0.23879 (6)	0.46250 (5)	0.08035 (18)
Cl2	0.14184 (5)	0.45480 (9)	0.57917 (6)	0.1019 (3)
O1	0.10827 (16)	0.35212 (16)	0.86276 (14)	0.0787 (4)
N1	0.22996 (13)	0.84151 (14)	1.00579 (11)	0.0461 (3)
N2	0.35901 (14)	0.86410 (14)	0.93127 (12)	0.0496 (3)
C1	0.4853 (2)	0.3081 (2)	0.76848 (16)	0.0634 (5)
H1A	0.5039	0.2962	0.8459	0.076*
C2	0.6034 (2)	0.2677 (2)	0.68476 (17)	0.0677 (5)
H2A	0.7000	0.2286	0.7056	0.081*
C3	0.57655 (18)	0.28591 (17)	0.57036 (15)	0.0537 (4)
C4	0.43478 (18)	0.34217 (18)	0.53839 (16)	0.0565 (4)
H4A	0.4175	0.3541	0.4606	0.068*
C5	0.31849 (17)	0.38071 (18)	0.62408 (16)	0.0526 (4)
C6	0.33961 (17)	0.36581 (16)	0.74104 (14)	0.0470 (3)
C7	0.21224 (19)	0.40361 (18)	0.83561 (15)	0.0536 (4)
C8	0.21287 (19)	0.50151 (19)	0.89386 (15)	0.0570 (4)
H8A	0.1421	0.5086	0.9621	0.068*
C9	0.30613 (17)	0.58143 (16)	0.85751 (13)	0.0466 (3)
H9A	0.3819	0.5680	0.7937	0.056*
C10	0.30113 (16)	0.68689 (16)	0.90744 (13)	0.0452 (3)
C11	0.19295 (17)	0.73726 (17)	0.99304 (14)	0.0481 (3)
H11A	0.1098	0.7049	1.0343	0.058*
C12	0.40123 (16)	0.77075 (16)	0.87221 (14)	0.0452 (3)
C13	0.53890 (16)	0.76264 (17)	0.78363 (14)	0.0478 (3)
C14	0.5637 (2)	0.8813 (2)	0.68817 (19)	0.0703 (5)
H14A	0.4923	0.9684	0.6784	0.084*
C15	0.6947 (3)	0.8706 (3)	0.6070 (2)	0.0862 (7)
H15A	0.7098	0.9505	0.5420	0.103*
C16	0.8019 (2)	0.7449 (3)	0.6209 (2)	0.0785 (6)
H16A	0.8902	0.7395	0.5666	0.094*
C17	0.7792 (2)	0.6270 (2)	0.71462 (19)	0.0711 (5)
H17A	0.8523	0.5410	0.7244	0.085*
C18	0.64774 (18)	0.6348 (2)	0.79530 (16)	0.0580 (4)
H18A	0.6323	0.5535	0.8580	0.070*
C19	0.15658 (16)	0.92254 (17)	1.08631 (14)	0.0488 (4)
C20	0.03696 (19)	0.8896 (2)	1.17154 (17)	0.0612 (4)
H20A	0.0011	0.8173	1.1752	0.073*
C21	−0.0289 (2)	0.9666 (3)	1.25176 (19)	0.0756 (6)
H21A	−0.1097	0.9455	1.3097	0.091*
C22	0.0236 (2)	1.0730 (3)	1.2467 (2)	0.0799 (6)
H22A	−0.0205	1.1228	1.3018	0.096*
C23	0.1411 (2)	1.1064 (2)	1.1603 (2)	0.0755 (6)
H23A	0.1757	1.1797	1.1561	0.091*
C24	0.2084 (2)	1.03114 (19)	1.07925 (17)	0.0609 (4)
H24A	0.2880	1.0538	1.0205	0.073*

	U11	U22	U33	U12	U13	U23
Cl1	0.0657 (3)	0.0801 (3)	0.0695 (3)	0.0003 (2)	0.0118 (2)	−0.0280 (3)
Cl2	0.0469 (3)	0.1805 (7)	0.1026 (4)	0.0004 (3)	−0.0210 (3)	−0.0934 (5)
O1	0.0746 (8)	0.1027 (10)	0.0849 (10)	−0.0569 (8)	0.0247 (7)	−0.0516 (8)
N1	0.0409 (6)	0.0555 (7)	0.0445 (7)	−0.0107 (5)	−0.0034 (5)	−0.0228 (6)
N2	0.0432 (6)	0.0584 (8)	0.0514 (7)	−0.0148 (6)	0.0002 (5)	−0.0258 (6)
C1	0.0607 (10)	0.0753 (11)	0.0465 (9)	−0.0052 (9)	−0.0152 (8)	−0.0190 (8)
C2	0.0498 (9)	0.0772 (12)	0.0580 (10)	0.0050 (8)	−0.0153 (8)	−0.0180 (9)
C3	0.0512 (8)	0.0471 (8)	0.0515 (9)	−0.0044 (7)	0.0001 (7)	−0.0165 (7)
C4	0.0537 (9)	0.0680 (10)	0.0519 (9)	−0.0095 (8)	−0.0069 (7)	−0.0306 (8)
C5	0.0435 (8)	0.0643 (10)	0.0600 (9)	−0.0117 (7)	−0.0080 (7)	−0.0330 (8)
C6	0.0491 (8)	0.0494 (8)	0.0472 (8)	−0.0172 (6)	−0.0011 (6)	−0.0210 (6)
C7	0.0549 (9)	0.0619 (9)	0.0507 (9)	−0.0251 (8)	0.0054 (7)	−0.0255 (7)
C8	0.0576 (9)	0.0704 (10)	0.0515 (9)	−0.0284 (8)	0.0132 (7)	−0.0321 (8)
C9	0.0467 (8)	0.0563 (9)	0.0390 (7)	−0.0165 (7)	0.0010 (6)	−0.0200 (6)
C10	0.0448 (7)	0.0514 (8)	0.0404 (7)	−0.0147 (6)	−0.0022 (6)	−0.0171 (6)
C11	0.0446 (7)	0.0584 (9)	0.0446 (8)	−0.0175 (7)	−0.0006 (6)	−0.0209 (7)
C12	0.0414 (7)	0.0522 (8)	0.0430 (8)	−0.0118 (6)	−0.0037 (6)	−0.0190 (6)
C13	0.0444 (8)	0.0591 (9)	0.0471 (8)	−0.0187 (7)	0.0000 (6)	−0.0250 (7)
C14	0.0740 (12)	0.0622 (11)	0.0730 (12)	−0.0283 (9)	0.0118 (10)	−0.0255 (9)
C15	0.0974 (16)	0.0867 (15)	0.0792 (14)	−0.0554 (13)	0.0292 (12)	−0.0311 (12)
C16	0.0657 (12)	0.1101 (17)	0.0835 (14)	−0.0461 (12)	0.0260 (10)	−0.0599 (14)
C17	0.0497 (9)	0.0921 (14)	0.0775 (13)	−0.0128 (9)	0.0048 (9)	−0.0482 (12)
C18	0.0497 (9)	0.0676 (10)	0.0536 (9)	−0.0132 (8)	−0.0020 (7)	−0.0223 (8)
C19	0.0430 (7)	0.0575 (9)	0.0451 (8)	−0.0012 (6)	−0.0116 (6)	−0.0238 (7)
C20	0.0487 (9)	0.0821 (12)	0.0594 (10)	−0.0145 (8)	−0.0031 (7)	−0.0360 (9)
C21	0.0540 (10)	0.1103 (17)	0.0666 (12)	−0.0113 (10)	0.0016 (9)	−0.0495 (12)
C22	0.0712 (12)	0.0989 (16)	0.0786 (14)	−0.0009 (11)	−0.0085 (11)	−0.0595 (13)
C23	0.0809 (13)	0.0743 (12)	0.0820 (14)	−0.0099 (10)	−0.0114 (11)	−0.0467 (11)
C24	0.0642 (10)	0.0610 (10)	0.0605 (10)	−0.0121 (8)	−0.0050 (8)	−0.0297 (8)

Cl1—C3	1.7369 (16)	C11—H11A	0.9300
Cl2—C5	1.7304 (16)	C12—C13	1.474 (2)
O1—C7	1.2196 (19)	C13—C14	1.382 (2)
N1—C11	1.346 (2)	C13—C18	1.385 (2)
N1—N2	1.3718 (17)	C14—C15	1.385 (3)
N1—C19	1.4283 (19)	C14—H14A	0.9300
N2—C12	1.3282 (19)	C15—C16	1.360 (3)
C1—C2	1.378 (3)	C15—H15A	0.9300
C1—C6	1.388 (2)	C16—C17	1.362 (3)
C1—H1A	0.9300	C16—H16A	0.9300
C2—C3	1.370 (3)	C17—C18	1.384 (2)
C2—H2A	0.9300	C17—H17A	0.9300
C3—C4	1.371 (2)	C18—H18A	0.9300
C4—C5	1.378 (2)	C19—C24	1.377 (2)
C4—H4A	0.9300	C19—C20	1.379 (2)
C5—C6	1.391 (2)	C20—C21	1.388 (3)
C6—C7	1.501 (2)	C20—H20A	0.9300
C7—C8	1.458 (2)	C21—C22	1.368 (3)
C8—C9	1.330 (2)	C21—H21A	0.9300
C8—H8A	0.9300	C22—C23	1.371 (3)
C9—C10	1.441 (2)	C22—H22A	0.9300
C9—H9A	0.9300	C23—C24	1.384 (3)
C10—C11	1.385 (2)	C23—H23A	0.9300
C10—C12	1.416 (2)	C24—H24A	0.9300
C11—N1—N2	111.74 (12)	N2—C12—C13	120.29 (14)
C11—N1—C19	128.80 (13)	C10—C12—C13	127.91 (13)
N2—N1—C19	119.42 (13)	C14—C13—C18	118.39 (15)
C12—N2—N1	104.76 (12)	C14—C13—C12	121.32 (15)
C2—C1—C6	122.13 (16)	C18—C13—C12	120.28 (15)
C2—C1—H1A	118.9	C13—C14—C15	119.99 (19)
C6—C1—H1A	118.9	C13—C14—H14A	120.0
C3—C2—C1	119.06 (16)	C15—C14—H14A	120.0
C3—C2—H2A	120.5	C16—C15—C14	121.0 (2)
C1—C2—H2A	120.5	C16—C15—H15A	119.5
C2—C3—C4	121.28 (15)	C14—C15—H15A	119.5
C2—C3—Cl1	119.79 (13)	C15—C16—C17	119.70 (18)
C4—C3—Cl1	118.92 (13)	C15—C16—H16A	120.1
C3—C4—C5	118.53 (15)	C17—C16—H16A	120.1
C3—C4—H4A	120.7	C16—C17—C18	120.23 (19)
C5—C4—H4A	120.7	C16—C17—H17A	119.9
C4—C5—C6	122.56 (14)	C18—C17—H17A	119.9
C4—C5—Cl2	117.16 (12)	C17—C18—C13	120.67 (17)
C6—C5—Cl2	120.25 (12)	C17—C18—H18A	119.7
C1—C6—C5	116.43 (14)	C13—C18—H18A	119.7
C1—C6—C7	121.05 (14)	C24—C19—C20	120.82 (15)
C5—C6—C7	122.46 (14)	C24—C19—N1	119.36 (15)
O1—C7—C8	120.46 (15)	C20—C19—N1	119.81 (15)
O1—C7—C6	119.38 (15)	C19—C20—C21	118.66 (19)
C8—C7—C6	120.16 (14)	C19—C20—H20A	120.7
C9—C8—C7	125.46 (15)	C21—C20—H20A	120.7
C9—C8—H8A	117.3	C22—C21—C20	120.8 (2)
C7—C8—H8A	117.3	C22—C21—H21A	119.6
C8—C9—C10	126.31 (14)	C20—C21—H21A	119.6
C8—C9—H9A	116.8	C21—C22—C23	120.02 (19)
C10—C9—H9A	116.8	C21—C22—H22A	120.0
C11—C10—C12	104.10 (13)	C23—C22—H22A	120.0
C11—C10—C9	128.48 (14)	C22—C23—C24	120.2 (2)
C12—C10—C9	127.26 (13)	C22—C23—H23A	119.9
N1—C11—C10	107.60 (13)	C24—C23—H23A	119.9
N1—C11—H11A	126.2	C19—C24—C23	119.49 (18)
C10—C11—H11A	126.2	C19—C24—H24A	120.3
N2—C12—C10	111.80 (13)	C23—C24—H24A	120.3
C11—N1—N2—C12	−0.17 (16)	N1—N2—C12—C13	−179.30 (13)
C19—N1—N2—C12	177.93 (12)	C11—C10—C12—N2	0.29 (17)
C6—C1—C2—C3	0.5 (3)	C9—C10—C12—N2	175.95 (14)
C1—C2—C3—C4	−0.6 (3)	C11—C10—C12—C13	179.43 (15)
C1—C2—C3—Cl1	178.80 (15)	C9—C10—C12—C13	−4.9 (3)
C2—C3—C4—C5	0.1 (3)	N2—C12—C13—C14	−52.8 (2)
Cl1—C3—C4—C5	−179.29 (13)	C10—C12—C13—C14	128.08 (19)
C3—C4—C5—C6	0.5 (3)	N2—C12—C13—C18	126.52 (17)
C3—C4—C5—Cl2	178.65 (14)	C10—C12—C13—C18	−52.6 (2)
C2—C1—C6—C5	0.1 (3)	C18—C13—C14—C15	0.1 (3)
C2—C1—C6—C7	177.56 (17)	C12—C13—C14—C15	179.44 (18)
C4—C5—C6—C1	−0.7 (3)	C13—C14—C15—C16	−1.3 (4)
Cl2—C5—C6—C1	−178.70 (14)	C14—C15—C16—C17	1.2 (4)
C4—C5—C6—C7	−178.03 (16)	C15—C16—C17—C18	0.1 (3)
Cl2—C5—C6—C7	3.9 (2)	C16—C17—C18—C13	−1.3 (3)
C1—C6—C7—O1	−123.5 (2)	C14—C13—C18—C17	1.2 (3)
C5—C6—C7—O1	53.8 (2)	C12—C13—C18—C17	−178.17 (16)
C1—C6—C7—C8	56.8 (2)	C11—N1—C19—C24	−176.03 (15)
C5—C6—C7—C8	−125.95 (18)	N2—N1—C19—C24	6.2 (2)
O1—C7—C8—C9	−168.14 (18)	C11—N1—C19—C20	5.2 (2)
C6—C7—C8—C9	11.6 (3)	N2—N1—C19—C20	−172.51 (14)
C7—C8—C9—C10	174.67 (16)	C24—C19—C20—C21	−1.1 (3)
C8—C9—C10—C11	−7.0 (3)	N1—C19—C20—C21	177.64 (16)
C8—C9—C10—C12	178.37 (17)	C19—C20—C21—C22	0.0 (3)
N2—N1—C11—C10	0.35 (17)	C20—C21—C22—C23	1.0 (3)
C19—N1—C11—C10	−177.52 (14)	C21—C22—C23—C24	−1.0 (3)
C12—C10—C11—N1	−0.37 (16)	C20—C19—C24—C23	1.2 (3)
C9—C10—C11—N1	−175.96 (14)	N1—C19—C24—C23	−177.55 (16)
N1—N2—C12—C10	−0.08 (16)	C22—C23—C24—C19	−0.1 (3)

Cg1 and Cg2 are the centroids of the C19–C24 and C13–C18 benzene rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11A···O1i	0.93	2.30	3.230 (2)	174
C20—H20A···O1i	0.93	2.59	3.509 (3)	168
C2—H2A···Cg1ii	0.93	2.75	3.585 (2)	149
C23—H23A···Cg2iii	0.93	2.90	3.655 (2)	140

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C19–C24 and C13–C18 benzene rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C11—H11A⋯O1i	0.93	2.30	3.230 (2)	174
C20—H20A⋯O1i	0.93	2.59	3.509 (3)	168
C2—H2A⋯Cg1ii	0.93	2.75	3.585 (2)	149
C23—H23A⋯Cg2iii	0.93	2.90	3.655 (2)	140

Symmetry codes: (i) ; (ii) ; (iii) .