(E)-3-[3-(4-Bromo-phen-yl)-1-phenyl-1H-pyrazol-4-yl]-1-(2,4-dichloro-phen-yl)prop-2-en-1-one.

In the title mol-ecule, C(24)H(15)BrCl(2)N(2)O, the dihedral angles betwen the pyrazole ring and its N-bonded phenyl (A) and C-bonded bromo-benzene (B) rings are 10.34 (16) and 40.95 (15)°, respectively. The dihedral angle between rings A and B is 56.89 (17)°. The title mol-ecule exists in a trans conformation with respect to the acyclic C=C bond. In the crystal, mol-ecules are linked into inversion dimers by pairs of C-H⋯O hydrogen bonds, generating R(2) (2)(14) loops. The crystal structure is further consolidated by C-H⋯π inter-actions.

Related literature

For a related structure and background references to pyrazoles, see: Fun et al. (2011 ▶). For standard bond-length data, see: Allen et al. (1987 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C24H15BrCl2N2O

M = 498.19

Monoclinic,

a = 11.4203 (14) Å

b = 9.9357 (13) Å

c = 19.656 (3) Å

β = 94.653 (3)°

V = 2222.9 (5) Å3

Z = 4

Mo Kα radiation

μ = 2.11 mm−1

T = 296 K

0.38 × 0.21 × 0.11 mm

Data collection

Bruker SMART APEXII DUO CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.504, T max = 0.803

23842 measured reflections

6480 independent reflections

2743 reflections with I > 2σ(I)

R int = 0.056

Refinement

R[F 2 > 2σ(F 2)] = 0.052

wR(F 2) = 0.140

S = 0.98

6480 reflections

271 parameters

H-atom parameters constrained

Δρmax = 0.44 e Å−3

Δρmin = −0.52 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/S1600536811044424/hb6462sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811044424/hb6462Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811044424/hb6462Isup3.cml

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

C24H15BrCl2N2O	F(000) = 1000
Mr = 498.19	Dx = 1.489 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2554 reflections
a = 11.4203 (14) Å	θ = 2.9–22.2°
b = 9.9357 (13) Å	µ = 2.11 mm−1
c = 19.656 (3) Å	T = 296 K
β = 94.653 (3)°	Block, colourless
V = 2222.9 (5) Å3	0.38 × 0.21 × 0.11 mm
Z = 4

Bruker SMART APEXII DUO CCD diffractometer	6480 independent reflections
Radiation source: fine-focus sealed tube	2743 reflections with I > 2σ(I)
graphite	Rint = 0.056
φ and ω scans	θmax = 30.1°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −15→16
Tmin = 0.504, Tmax = 0.803	k = −13→13
23842 measured reflections	l = −27→22

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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.140	H-atom parameters constrained
S = 0.98	w = 1/[σ2(Fo2) + (0.0493P)2 + 0.6604P] where P = (Fo2 + 2Fc2)/3
6480 reflections	(Δ/σ)max = 0.001
271 parameters	Δρmax = 0.44 e Å−3
0 restraints	Δρmin = −0.52 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
Br1	0.29004 (5)	−0.10153 (6)	0.11448 (2)	0.1353 (3)
O1	0.12637 (19)	0.64502 (19)	0.42799 (11)	0.0738 (6)
N1	−0.10263 (19)	0.0347 (2)	0.43425 (11)	0.0521 (5)
N2	−0.05301 (19)	−0.0315 (2)	0.38311 (10)	0.0532 (6)
C1	0.2092 (3)	0.4905 (3)	0.28237 (14)	0.0621 (7)
H1A	0.1332	0.4616	0.2693	0.075*
C2	0.2907 (3)	0.4908 (4)	0.23478 (16)	0.0844 (10)
H2A	0.2701	0.4629	0.1903	0.101*
C3	0.4027 (3)	0.5329 (5)	0.2538 (2)	0.0960 (12)
C4	0.4336 (3)	0.5741 (4)	0.31980 (19)	0.0865 (11)
H4A	0.5097	0.6028	0.3325	0.104*
C5	0.3506 (3)	0.5722 (3)	0.36638 (15)	0.0624 (8)
C6	0.2362 (2)	0.5316 (3)	0.34922 (13)	0.0509 (6)
C7	0.1426 (2)	0.5391 (3)	0.39854 (14)	0.0535 (7)
C8	0.0702 (2)	0.4217 (3)	0.40921 (15)	0.0562 (7)
H8A	0.0056	0.4330	0.4346	0.067*
C9	0.0901 (2)	0.2988 (3)	0.38512 (14)	0.0528 (7)
H9A	0.1547	0.2885	0.3597	0.063*
C10	0.0198 (2)	0.1802 (3)	0.39515 (14)	0.0510 (6)
C11	−0.0605 (2)	0.1606 (3)	0.44253 (14)	0.0546 (7)
H11A	−0.0818	0.2231	0.4745	0.065*
C12	0.0218 (2)	0.0567 (3)	0.35954 (13)	0.0499 (6)
C13	0.0901 (2)	0.0206 (3)	0.30199 (13)	0.0513 (6)
C14	0.1383 (3)	−0.1062 (3)	0.29778 (16)	0.0647 (8)
H14A	0.1302	−0.1678	0.3327	0.078*
C15	0.1984 (3)	−0.1429 (3)	0.24257 (18)	0.0773 (9)
H15A	0.2302	−0.2288	0.2401	0.093*
C16	0.2106 (3)	−0.0517 (4)	0.19150 (16)	0.0771 (10)
C17	0.1647 (3)	0.0740 (4)	0.19476 (17)	0.0854 (11)
H17A	0.1741	0.1356	0.1600	0.102*
C18	0.1042 (3)	0.1099 (3)	0.24994 (15)	0.0700 (8)
H18A	0.0724	0.1959	0.2519	0.084*
C19	−0.1936 (2)	−0.0283 (3)	0.46832 (13)	0.0538 (7)
C20	−0.2579 (3)	0.0449 (3)	0.51087 (17)	0.0778 (9)
H20A	−0.2423	0.1359	0.5180	0.093*
C21	−0.3459 (3)	−0.0174 (4)	0.54300 (19)	0.0943 (12)
H21A	−0.3899	0.0325	0.5718	0.113*
C22	−0.3699 (3)	−0.1507 (4)	0.53335 (19)	0.0871 (10)
H22A	−0.4294	−0.1918	0.5554	0.105*
C23	−0.3047 (3)	−0.2235 (4)	0.49049 (19)	0.0845 (10)
H23A	−0.3209	−0.3142	0.4830	0.101*
C24	−0.2153 (3)	−0.1630 (3)	0.45838 (16)	0.0695 (8)
H24A	−0.1702	−0.2131	0.4302	0.083*
Cl1	0.50704 (12)	0.5349 (2)	0.19526 (7)	0.1885 (8)
Cl2	0.39593 (8)	0.61893 (11)	0.44937 (5)	0.0945 (3)

	U11	U22	U33	U12	U13	U23
Br1	0.1461 (4)	0.1639 (5)	0.1070 (4)	−0.0726 (3)	0.0781 (3)	−0.0677 (3)
O1	0.0941 (15)	0.0484 (12)	0.0836 (15)	−0.0100 (11)	0.0363 (12)	−0.0172 (11)
N1	0.0620 (14)	0.0463 (13)	0.0487 (13)	−0.0033 (11)	0.0081 (11)	−0.0024 (10)
N2	0.0659 (14)	0.0474 (13)	0.0470 (12)	−0.0023 (11)	0.0095 (11)	−0.0052 (10)
C1	0.0677 (18)	0.0636 (19)	0.0544 (17)	0.0069 (15)	0.0012 (15)	−0.0050 (14)
C2	0.094 (3)	0.111 (3)	0.0498 (18)	0.027 (2)	0.0131 (18)	−0.0086 (18)
C3	0.077 (3)	0.145 (4)	0.070 (2)	0.030 (2)	0.029 (2)	0.007 (2)
C4	0.061 (2)	0.122 (3)	0.078 (2)	0.0072 (19)	0.0142 (18)	0.008 (2)
C5	0.0647 (19)	0.069 (2)	0.0535 (17)	0.0039 (15)	0.0037 (15)	0.0011 (14)
C6	0.0591 (17)	0.0442 (15)	0.0496 (15)	0.0033 (13)	0.0059 (13)	−0.0035 (12)
C7	0.0624 (17)	0.0453 (16)	0.0533 (16)	−0.0009 (13)	0.0083 (13)	−0.0038 (13)
C8	0.0584 (17)	0.0479 (17)	0.0641 (18)	−0.0018 (13)	0.0156 (14)	−0.0037 (13)
C9	0.0557 (16)	0.0499 (17)	0.0529 (16)	−0.0017 (13)	0.0058 (13)	−0.0014 (13)
C10	0.0548 (16)	0.0441 (16)	0.0539 (16)	−0.0021 (12)	0.0032 (13)	−0.0049 (12)
C11	0.0648 (17)	0.0405 (16)	0.0590 (17)	−0.0009 (13)	0.0086 (14)	−0.0088 (12)
C12	0.0584 (16)	0.0434 (16)	0.0476 (15)	0.0007 (13)	0.0028 (13)	0.0002 (12)
C13	0.0616 (16)	0.0436 (16)	0.0487 (15)	−0.0071 (13)	0.0037 (13)	−0.0040 (12)
C14	0.077 (2)	0.0516 (19)	0.0670 (19)	−0.0017 (15)	0.0178 (16)	0.0001 (14)
C15	0.089 (2)	0.060 (2)	0.087 (2)	−0.0033 (17)	0.034 (2)	−0.0154 (18)
C16	0.083 (2)	0.086 (3)	0.065 (2)	−0.0349 (19)	0.0275 (17)	−0.0257 (18)
C17	0.126 (3)	0.079 (3)	0.0539 (19)	−0.032 (2)	0.021 (2)	0.0017 (17)
C18	0.099 (2)	0.0571 (19)	0.0543 (18)	−0.0068 (17)	0.0096 (17)	0.0015 (14)
C19	0.0604 (17)	0.0539 (17)	0.0463 (15)	−0.0079 (14)	−0.0007 (13)	0.0022 (13)
C20	0.089 (2)	0.065 (2)	0.084 (2)	−0.0081 (17)	0.0355 (19)	−0.0082 (17)
C21	0.093 (3)	0.096 (3)	0.100 (3)	−0.016 (2)	0.045 (2)	−0.012 (2)
C22	0.084 (2)	0.098 (3)	0.082 (2)	−0.030 (2)	0.020 (2)	0.003 (2)
C23	0.093 (2)	0.076 (2)	0.084 (2)	−0.032 (2)	0.006 (2)	−0.0035 (19)
C24	0.084 (2)	0.061 (2)	0.0650 (19)	−0.0174 (17)	0.0129 (17)	−0.0086 (15)
Cl1	0.1164 (9)	0.351 (2)	0.1079 (9)	0.0464 (13)	0.0678 (8)	0.0086 (13)
Cl2	0.0853 (6)	0.1270 (8)	0.0694 (6)	−0.0180 (5)	−0.0044 (5)	−0.0168 (5)

Br1—C16	1.893 (3)	C10—C12	1.414 (4)
O1—C7	1.222 (3)	C11—H11A	0.9300
N1—C11	1.346 (3)	C12—C13	1.469 (4)
N1—N2	1.363 (3)	C13—C18	1.374 (4)
N1—C19	1.425 (3)	C13—C14	1.380 (4)
N2—C12	1.333 (3)	C14—C15	1.379 (4)
C1—C2	1.372 (4)	C14—H14A	0.9300
C1—C6	1.387 (4)	C15—C16	1.368 (5)
C1—H1A	0.9300	C15—H15A	0.9300
C2—C3	1.369 (5)	C16—C17	1.358 (5)
C2—H2A	0.9300	C17—C18	1.380 (4)
C3—C4	1.378 (5)	C17—H17A	0.9300
C3—Cl1	1.723 (3)	C18—H18A	0.9300
C4—C5	1.370 (4)	C19—C20	1.367 (4)
C4—H4A	0.9300	C19—C24	1.373 (4)
C5—C6	1.384 (4)	C20—C21	1.377 (4)
C5—Cl2	1.734 (3)	C20—H20A	0.9300
C6—C7	1.502 (4)	C21—C22	1.363 (5)
C7—C8	1.455 (4)	C21—H21A	0.9300
C8—C9	1.336 (4)	C22—C23	1.374 (5)
C8—H8A	0.9300	C22—H22A	0.9300
C9—C10	1.448 (4)	C23—C24	1.380 (4)
C9—H9A	0.9300	C23—H23A	0.9300
C10—C11	1.373 (4)	C24—H24A	0.9300
C11—N1—N2	111.8 (2)	N2—C12—C13	120.2 (2)
C11—N1—C19	128.2 (2)	C10—C12—C13	128.6 (2)
N2—N1—C19	119.8 (2)	C18—C13—C14	118.3 (3)
C12—N2—N1	104.8 (2)	C18—C13—C12	121.1 (3)
C2—C1—C6	122.3 (3)	C14—C13—C12	120.5 (2)
C2—C1—H1A	118.8	C15—C14—C13	121.0 (3)
C6—C1—H1A	118.8	C15—C14—H14A	119.5
C3—C2—C1	119.0 (3)	C13—C14—H14A	119.5
C3—C2—H2A	120.5	C16—C15—C14	119.3 (3)
C1—C2—H2A	120.5	C16—C15—H15A	120.4
C2—C3—C4	120.7 (3)	C14—C15—H15A	120.4
C2—C3—Cl1	120.2 (3)	C17—C16—C15	120.8 (3)
C4—C3—Cl1	119.2 (3)	C17—C16—Br1	119.4 (3)
C5—C4—C3	119.1 (3)	C15—C16—Br1	119.8 (3)
C5—C4—H4A	120.4	C16—C17—C18	119.7 (3)
C3—C4—H4A	120.4	C16—C17—H17A	120.2
C4—C5—C6	122.1 (3)	C18—C17—H17A	120.2
C4—C5—Cl2	117.1 (3)	C13—C18—C17	121.0 (3)
C6—C5—Cl2	120.7 (2)	C13—C18—H18A	119.5
C5—C6—C1	116.7 (3)	C17—C18—H18A	119.5
C5—C6—C7	122.4 (2)	C20—C19—C24	120.4 (3)
C1—C6—C7	120.8 (2)	C20—C19—N1	120.1 (3)
O1—C7—C8	120.8 (3)	C24—C19—N1	119.5 (3)
O1—C7—C6	119.4 (2)	C19—C20—C21	119.3 (3)
C8—C7—C6	119.7 (2)	C19—C20—H20A	120.3
C9—C8—C7	124.5 (3)	C21—C20—H20A	120.3
C9—C8—H8A	117.7	C22—C21—C20	121.3 (3)
C7—C8—H8A	117.7	C22—C21—H21A	119.4
C8—C9—C10	125.7 (3)	C20—C21—H21A	119.4
C8—C9—H9A	117.2	C21—C22—C23	119.0 (3)
C10—C9—H9A	117.2	C21—C22—H22A	120.5
C11—C10—C12	104.6 (2)	C23—C22—H22A	120.5
C11—C10—C9	128.0 (2)	C22—C23—C24	120.6 (3)
C12—C10—C9	127.4 (2)	C22—C23—H23A	119.7
N1—C11—C10	107.6 (2)	C24—C23—H23A	119.7
N1—C11—H11A	126.2	C19—C24—C23	119.4 (3)
C10—C11—H11A	126.2	C19—C24—H24A	120.3
N2—C12—C10	111.2 (2)	C23—C24—H24A	120.3
C11—N1—N2—C12	0.1 (3)	C11—C10—C12—N2	0.7 (3)
C19—N1—N2—C12	176.1 (2)	C9—C10—C12—N2	178.7 (2)
C6—C1—C2—C3	0.1 (5)	C11—C10—C12—C13	178.5 (3)
C1—C2—C3—C4	0.1 (6)	C9—C10—C12—C13	−3.5 (4)
C1—C2—C3—Cl1	−179.9 (3)	N2—C12—C13—C18	136.9 (3)
C2—C3—C4—C5	0.1 (6)	C10—C12—C13—C18	−40.7 (4)
Cl1—C3—C4—C5	−179.8 (3)	N2—C12—C13—C14	−40.7 (4)
C3—C4—C5—C6	−0.7 (5)	C10—C12—C13—C14	141.6 (3)
C3—C4—C5—Cl2	177.6 (3)	C18—C13—C14—C15	−0.5 (5)
C4—C5—C6—C1	1.0 (4)	C12—C13—C14—C15	177.3 (3)
Cl2—C5—C6—C1	−177.2 (2)	C13—C14—C15—C16	0.3 (5)
C4—C5—C6—C7	−175.3 (3)	C14—C15—C16—C17	0.2 (5)
Cl2—C5—C6—C7	6.5 (4)	C14—C15—C16—Br1	−178.7 (2)
C2—C1—C6—C5	−0.7 (4)	C15—C16—C17—C18	−0.6 (5)
C2—C1—C6—C7	175.6 (3)	Br1—C16—C17—C18	178.4 (2)
C5—C6—C7—O1	51.9 (4)	C14—C13—C18—C17	0.1 (5)
C1—C6—C7—O1	−124.2 (3)	C12—C13—C18—C17	−177.6 (3)
C5—C6—C7—C8	−129.9 (3)	C16—C17—C18—C13	0.4 (5)
C1—C6—C7—C8	54.0 (4)	C11—N1—C19—C20	6.9 (4)
O1—C7—C8—C9	−172.3 (3)	N2—N1—C19—C20	−168.4 (3)
C6—C7—C8—C9	9.5 (4)	C11—N1—C19—C24	−172.7 (3)
C7—C8—C9—C10	179.8 (3)	N2—N1—C19—C24	12.0 (4)
C8—C9—C10—C11	−16.9 (5)	C24—C19—C20—C21	−0.9 (5)
C8—C9—C10—C12	165.5 (3)	N1—C19—C20—C21	179.6 (3)
N2—N1—C11—C10	0.3 (3)	C19—C20—C21—C22	0.2 (6)
C19—N1—C11—C10	−175.3 (2)	C20—C21—C22—C23	−0.2 (6)
C12—C10—C11—N1	−0.6 (3)	C21—C22—C23—C24	0.8 (6)
C9—C10—C11—N1	−178.6 (2)	C20—C19—C24—C23	1.5 (5)
N1—N2—C12—C10	−0.5 (3)	N1—C19—C24—C23	−178.9 (3)
N1—N2—C12—C13	−178.5 (2)	C22—C23—C24—C19	−1.5 (5)

Cg1 is the centroid of C1–C6 phenyl ring.

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11A···O1i	0.93	2.41	3.329 (4)	170
C15—H15A···Cg1ii	0.93	2.82	3.666 (3)	152

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of C1–C6 phenyl ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C11—H11A⋯O1i	0.93	2.41	3.329 (4)	170
C15—H15A⋯Cg1ii	0.93	2.82	3.666 (3)	152

Symmetry codes: (i) ; (ii) .