(E)-3-[3-(4-Bromo­phen­yl)-1-phenyl-1H-pyrazol-4-yl]-1-(2,4-dichloro­phen­yl)prop-2-en-1-one

Fun, H.-K.; Quah, C.K.; Malladi, S.; Isloor, A.M.; Shivananda, K.N.

doi:10.1107/S1600536811044424

organic compounds

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ISSN: 2056-9890

Volume 67| Part 11| November 2011| Page o3104

doi:10.1107/S1600536811044424

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(E)-3-[3-(4-Bromophenyl)-1-phenyl-1H-pyrazol-4-yl]-1-(2,4-dichlorophenyl)prop-2-en-1-one

Hoong-Kun Fun,^a ^*‡ Ching Kheng Quah,^a § Shridhar Malladi,^b Arun M. Isloor ^b and Kammasandra N. Shivananda ^c

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, ^bMedicinal Chemistry Division, Department of Chemistry, National Institute of Technology-Karnataka, Surathkal, Mangalore 575 025, India, and ^cSchulich Faculty of Chemistry, Technion Israel Institute of Technology, Haifa 32000, Israel
^*Correspondence e-mail: hkfun@usm.my

(Received 19 October 2011; accepted 25 October 2011; online 29 October 2011)

In the title molecule, C₂₄H₁₅BrCl₂N₂O, the dihedral angles betwen the pyrazole ring and its N-bonded phenyl (A) and C-bonded bromobenzene (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 molecule exists in a trans conformation with respect to the acyclic C=C bond. In the crystal, molecules are linked into inversion dimers by pairs of C—H⋯O hydrogen bonds, generating R²₂(14) loops. The crystal structure is further consolidated by C—H⋯π interactions.

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_r = 498.19
Monoclinic, P 2₁ /c
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[F² > 2σ(F²)] = 0.052
wR(F²) = 0.140
S = 0.98
6480 reflections
271 parameters
H-atom parameters constrained
Δρ_max = 0.44 e Å⁻³
Δρ_min = −0.52 e Å⁻³

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) -x, -y+1, -z+1; (ii) x, y-1, z.

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 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811044424/hb6462sup1.cif

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

Supporting information file. DOI: 10.1107/S1600536811044424/hb6462Isup3.cml

checkCIF report

Comment top

As part of our ongoing studies of pyrazole derivatives with potential biological activities (Fun et al., 2011), we have synthesized the title compound, (I), to study its crystal structure.

In the title molecule (Fig. 1), the benzene (C19-C24) ring and the two phenyl (C1-C6 and C13-C18) rings form dihedral angles of 10.34 (16), 50.23 (16) and 40.95 (15)°, respectively, with the pyrazole ring (N1/N2/C10-C12). The benzene ring also forms dihedral angles of 56.89 (17) and 38.81 (16)° with dichloro-bound phenyl (C1-C6) and bromo-bound phenyl (C13-C18) rings, respectively. The phenyl rings form a dihedral angle of 89.57 (17)°. The title molecule exists in trans configuration with respect to the acyclic C8═C9 bond [bond length = 1.336 (4) Å]. Bond lengths (Allen et al., 1987) and angles are within normal ranges and are comparable to a related structure (Fun et al., 2011).

In the crystal (Fig. 2), molecules are linked into inversion dimers by pairs of intermolecular C11–H11A···O1 hydrogen bonds (Table 1), generating fourteen-membered D²₂(14) ring motifs (Bernstein et al., 1995). The crystal structure is further consolidated by C15–H15A···Cg1 (Table 1) interactions, where Cg1 is the centroid of C1-C6 phenyl ring.

Related literature top

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 top

To a cold, stirred mixture of methanol (20 ml) and sodium hydroxide (12.09 mmol), 2,4-dichloroacetophenone (4.03 mmol) was added. The reaction mixture was stirred for 10 min. 3-(4-Bromophenyl)-1-phenyl-1H-pyrazole-4- carbaldehyde (4.03 mmol) was added to this solution followed by tetrahydrofuran (30 ml). The solution was further stirred for 2 h at 273 K and then at room temperature for 5 h. It was then poured into ice cold water. The resulting solution was neutralized with dil. HCl. The solid that separated out was filtered, washed with water, dried and crystallized from ethanol to yield colourless blocks. Yield: 1.6 g, 80 %. M.p.: 457-458 K.

Computing details top

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

Figures top

	Fig. 1. The molecular structure of the title compound showing 30% probability displacement ellipsoids for non-H atoms.
	Fig. 2. The crystal structure of the title compound, viewed along the b axis. H atoms not involved in hydrogen bonds (dashed lines) have been omitted for clarity.

(E)-3-[3-(4-Bromophenyl)-1-phenyl-1H-pyrazol-4-yl]-1- (2,4-dichlorophenyl)prop-2-en-1-one top

Crystal data top

C₂₄H₁₅BrCl₂N₂O	F(000) = 1000
M_r = 498.19	D_x = 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

Data collection top

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

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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.140	H-atom parameters constrained
S = 0.98	w = 1/[σ²(F_o²) + (0.0493P)² + 0.6604P] where P = (F_o² + 2F_c²)/3
6480 reflections	(Δ/σ)_max = 0.001
271 parameters	Δρ_max = 0.44 e Å⁻³
0 restraints	Δρ_min = −0.52 e Å⁻³

Crystal data top

C₂₄H₁₅BrCl₂N₂O	V = 2222.9 (5) Å³
M_r = 498.19	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 11.4203 (14) Å	µ = 2.11 mm⁻¹
b = 9.9357 (13) Å	T = 296 K
c = 19.656 (3) Å	0.38 × 0.21 × 0.11 mm
β = 94.653 (3)°

Data collection top

Bruker SMART APEXII DUO CCD diffractometer	6480 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	2743 reflections with I > 2σ(I)
T_min = 0.504, T_max = 0.803	R_int = 0.056
23842 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.052	0 restraints
wR(F²) = 0.140	H-atom parameters constrained
S = 0.98	Δρ_max = 0.44 e Å⁻³
6480 reflections	Δρ_min = −0.52 e Å⁻³
271 parameters

Special details top

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.

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

	x	y	z	U_iso*/U_eq
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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x, −y+1, −z+1; (ii) x, y−1, z.

Experimental details

Crystal data
Chemical formula	C₂₄H₁₅BrCl₂N₂O
M_r	498.19
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	11.4203 (14), 9.9357 (13), 19.656 (3)
β (°)	94.653 (3)
V (Å³)	2222.9 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	2.11
Crystal size (mm)	0.38 × 0.21 × 0.11

Data collection
Diffractometer	Bruker SMART APEXII DUO CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.504, 0.803
No. of measured, independent and observed [I > 2σ(I)] reflections	23842, 6480, 2743
R_int	0.056
(sin θ/λ)_max (Å⁻¹)	0.705

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.052, 0.140, 0.98
No. of reflections	6480
No. of parameters	271
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.44, −0.52

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

Hydrogen-bond geometry (Å, º) top

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) −x, −y+1, −z+1; (ii) x, y−1, z.

Footnotes

‡Thomson Reuters ResearcherID: A-3561-2009.

§Thomson Reuters ResearcherID: A-5525-2009.

Acknowledgements

HKF and CKQ thank Universiti Sains Malaysia for the Research University Grant (No. 1001/PFIZIK/811160). AMI is thankful to the Department of Atomic Energy, Board for Research in Nuclear Sciences, Government of India, for the Young Scientist award.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CrossRef Web of Science Google Scholar
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573. CrossRef CAS Web of Science Google Scholar
Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Fun, H.-K., Quah, C. K., Malladi, S., Isloor, A. M. & Shivananda, K. N. (2011). Acta Cryst. E67, o3102–o3103. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 67| Part 11| November 2011| Page o3104

doi:10.1107/S1600536811044424

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

(E)-3-[3-(4-Bromo­phen­yl)-1-phenyl-1H-pyrazol-4-yl]-1-(2,4-di­chloro­phen­yl)prop-2-en-1-one

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Experimental

Crystal data

Data collection

Refinement

Supporting information

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Acknowledgements

References

organic compounds

(E)-3-[3-(4-Bromophenyl)-1-phenyl-1H-pyrazol-4-yl]-1-(2,4-dichlorophenyl)prop-2-en-1-one