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

In the title mol-ecule, C(25)H(18)Cl(2)N(2)O(2), the dihedral angles between the pyrazole ring and its N- and C-bonded benzene rings are 8.28 (11) and 40.89 (10)°, respectively. The dihedral angle between the benzene rings is 39.03 (11)°. 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 inter-molecular C-H⋯O hydrogen bonds, generating R(2) (2)(14) loops.

Related literature

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

Experimental

Crystal data

C25H18Cl2N2O2

M = 449.31

Monoclinic,

a = 11.5037 (9) Å

b = 9.9197 (8) Å

c = 19.6867 (16) Å

β = 94.986 (2)°

V = 2238.0 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.31 mm−1

T = 296 K

0.42 × 0.26 × 0.20 mm

Data collection

Bruker SMART APEXII DUO CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.879, T max = 0.940

24117 measured reflections

6481 independent reflections

3796 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.053

wR(F 2) = 0.155

S = 1.02

6481 reflections

281 parameters

H-atom parameters constrained

Δρmax = 0.30 e Å−3

Δρmin = −0.40 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/S1600536811044400/hb6463sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811044400/hb6463Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811044400/hb6463Isup3.cml

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

C25H18Cl2N2O2	F(000) = 928
Mr = 449.31	Dx = 1.334 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4457 reflections
a = 11.5037 (9) Å	θ = 2.6–24.4°
b = 9.9197 (8) Å	µ = 0.31 mm−1
c = 19.6867 (16) Å	T = 296 K
β = 94.986 (2)°	Block, colourless
V = 2238.0 (3) Å3	0.42 × 0.26 × 0.20 mm
Z = 4

Bruker SMART APEXII DUO CCD diffractometer	6481 independent reflections
Radiation source: fine-focus sealed tube	3796 reflections with I > 2σ(I)
graphite	Rint = 0.031
φ and ω scans	θmax = 30.0°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −16→16
Tmin = 0.879, Tmax = 0.940	k = −11→13
24117 measured reflections	l = −27→27

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)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.155	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.059P)2 + 0.6136P] where P = (Fo2 + 2Fc2)/3
6481 reflections	(Δ/σ)max = 0.001
281 parameters	Δρmax = 0.30 e Å−3
0 restraints	Δρmin = −0.40 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	−0.00506 (8)	0.00115 (14)	0.29747 (5)	0.1569 (5)
Cl2	0.10909 (6)	−0.10965 (8)	0.04695 (4)	0.1029 (3)
O1	0.37565 (15)	−0.14366 (14)	0.07044 (8)	0.0792 (5)
O2	0.22210 (16)	0.57128 (19)	0.35788 (8)	0.0895 (5)
N1	0.60809 (12)	0.46755 (15)	0.06399 (7)	0.0491 (3)
N2	0.55921 (13)	0.53315 (15)	0.11542 (7)	0.0503 (3)
C1	0.29601 (17)	0.0166 (2)	0.21442 (10)	0.0587 (5)
H1A	0.3728	0.0399	0.2281	0.070*
C2	0.2134 (2)	0.0251 (3)	0.26089 (11)	0.0758 (6)
H2A	0.2339	0.0536	0.3053	0.091*
C3	0.1008 (2)	−0.0092 (3)	0.24031 (14)	0.0864 (8)
C4	0.06896 (18)	−0.0522 (3)	0.17537 (14)	0.0815 (7)
H4A	−0.0080	−0.0758	0.1623	0.098*
C5	0.15265 (18)	−0.0601 (2)	0.12960 (11)	0.0630 (5)
C6	0.26828 (15)	−0.02566 (18)	0.14784 (9)	0.0503 (4)
C7	0.36214 (17)	−0.03724 (19)	0.09968 (10)	0.0544 (4)
C8	0.43666 (16)	0.07857 (18)	0.08997 (10)	0.0556 (4)
H8A	0.5025	0.0649	0.0666	0.067*
C9	0.41725 (15)	0.20262 (18)	0.11213 (9)	0.0506 (4)
H9A	0.3518	0.2145	0.1361	0.061*
C10	0.48768 (14)	0.32072 (17)	0.10265 (9)	0.0484 (4)
C11	0.56707 (15)	0.34103 (18)	0.05548 (9)	0.0521 (4)
H11A	0.5886	0.2788	0.0235	0.063*
C12	0.48548 (14)	0.44448 (17)	0.13854 (9)	0.0464 (4)
C13	0.41627 (15)	0.47995 (17)	0.19521 (9)	0.0474 (4)
C14	0.40070 (18)	0.3886 (2)	0.24752 (10)	0.0600 (5)
H14A	0.4345	0.3035	0.2465	0.072*
C15	0.3361 (2)	0.4226 (2)	0.30053 (10)	0.0692 (6)
H15A	0.3265	0.3604	0.3350	0.083*
C16	0.28559 (18)	0.5482 (2)	0.30297 (10)	0.0621 (5)
C17	0.30101 (18)	0.6408 (2)	0.25277 (10)	0.0602 (5)
H17A	0.2681	0.7263	0.2546	0.072*
C18	0.36598 (16)	0.60618 (18)	0.19929 (10)	0.0536 (4)
H18A	0.3760	0.6692	0.1653	0.064*
C20	0.69679 (15)	0.5328 (2)	0.03000 (9)	0.0523 (4)
C21	0.7582 (2)	0.4611 (2)	−0.01461 (12)	0.0750 (6)
H21A	0.7418	0.3706	−0.0231	0.090*
C22	0.8442 (2)	0.5251 (3)	−0.04652 (15)	0.0998 (9)
H22A	0.8861	0.4773	−0.0769	0.120*
C23	0.8693 (2)	0.6584 (3)	−0.03433 (15)	0.0954 (9)
H23A	0.9278	0.7005	−0.0563	0.114*
C24	0.8083 (2)	0.7289 (3)	0.01009 (13)	0.0868 (8)
H24A	0.8260	0.8190	0.0191	0.104*
C25	0.7199 (2)	0.6667 (2)	0.04183 (11)	0.0701 (6)
H25A	0.6765	0.7155	0.0710	0.084*
C19	0.1650 (3)	0.6978 (3)	0.36102 (15)	0.1027 (9)
H19A	0.1246	0.7019	0.4016	0.154*
H19B	0.1101	0.7081	0.3218	0.154*
H19C	0.2217	0.7688	0.3618	0.154*

	U11	U22	U33	U12	U13	U23
Cl1	0.0996 (6)	0.2564 (14)	0.1240 (7)	0.0561 (7)	0.0633 (5)	0.0367 (8)
Cl2	0.0988 (5)	0.1161 (6)	0.0880 (5)	−0.0188 (4)	−0.0244 (4)	−0.0211 (4)
O1	0.1073 (12)	0.0476 (8)	0.0883 (11)	−0.0132 (8)	0.0403 (9)	−0.0177 (7)
O2	0.1016 (12)	0.1057 (14)	0.0668 (10)	−0.0030 (10)	0.0394 (9)	−0.0014 (9)
N1	0.0534 (8)	0.0454 (8)	0.0492 (8)	−0.0048 (6)	0.0081 (6)	−0.0045 (6)
N2	0.0573 (8)	0.0455 (8)	0.0490 (8)	−0.0038 (7)	0.0088 (6)	−0.0049 (6)
C1	0.0565 (10)	0.0626 (12)	0.0565 (11)	0.0029 (9)	0.0020 (8)	−0.0010 (9)
C2	0.0789 (14)	0.0938 (17)	0.0554 (12)	0.0208 (13)	0.0093 (10)	−0.0001 (11)
C3	0.0659 (13)	0.118 (2)	0.0787 (17)	0.0219 (13)	0.0242 (12)	0.0180 (15)
C4	0.0486 (11)	0.0994 (19)	0.0966 (19)	0.0007 (11)	0.0074 (11)	0.0119 (15)
C5	0.0606 (11)	0.0604 (12)	0.0665 (12)	−0.0041 (9)	−0.0029 (9)	0.0034 (9)
C6	0.0542 (9)	0.0415 (9)	0.0554 (10)	−0.0023 (7)	0.0057 (8)	0.0001 (7)
C7	0.0650 (11)	0.0438 (10)	0.0555 (10)	−0.0032 (8)	0.0108 (8)	−0.0046 (8)
C8	0.0578 (10)	0.0458 (10)	0.0648 (11)	−0.0031 (8)	0.0153 (8)	−0.0049 (8)
C9	0.0497 (9)	0.0469 (10)	0.0556 (10)	−0.0028 (7)	0.0071 (7)	−0.0034 (8)
C10	0.0489 (9)	0.0416 (9)	0.0548 (10)	−0.0016 (7)	0.0054 (7)	−0.0034 (7)
C11	0.0551 (9)	0.0448 (10)	0.0570 (11)	−0.0029 (8)	0.0079 (8)	−0.0092 (8)
C12	0.0498 (9)	0.0409 (9)	0.0482 (9)	−0.0011 (7)	0.0032 (7)	−0.0005 (7)
C13	0.0517 (9)	0.0438 (9)	0.0467 (9)	−0.0055 (7)	0.0050 (7)	−0.0024 (7)
C14	0.0737 (12)	0.0477 (11)	0.0587 (11)	0.0003 (9)	0.0058 (9)	0.0060 (8)
C15	0.0894 (15)	0.0674 (14)	0.0521 (11)	−0.0092 (11)	0.0145 (10)	0.0130 (9)
C16	0.0651 (11)	0.0712 (14)	0.0519 (11)	−0.0090 (10)	0.0161 (9)	−0.0051 (9)
C17	0.0676 (11)	0.0531 (11)	0.0622 (12)	0.0009 (9)	0.0184 (9)	−0.0050 (9)
C18	0.0636 (10)	0.0436 (10)	0.0551 (10)	−0.0034 (8)	0.0132 (8)	0.0018 (8)
C20	0.0517 (9)	0.0572 (11)	0.0478 (10)	−0.0065 (8)	0.0037 (7)	0.0017 (8)
C21	0.0760 (14)	0.0707 (14)	0.0826 (15)	−0.0097 (11)	0.0314 (12)	−0.0063 (12)
C22	0.0927 (18)	0.112 (2)	0.102 (2)	−0.0194 (17)	0.0487 (16)	−0.0093 (17)
C23	0.0801 (16)	0.119 (2)	0.0897 (19)	−0.0360 (16)	0.0247 (14)	0.0108 (16)
C24	0.0942 (17)	0.0819 (17)	0.0840 (17)	−0.0398 (14)	0.0068 (14)	0.0048 (13)
C25	0.0831 (14)	0.0645 (14)	0.0639 (13)	−0.0221 (11)	0.0124 (10)	−0.0057 (10)
C19	0.110 (2)	0.113 (2)	0.0925 (19)	0.0034 (18)	0.0490 (16)	−0.0307 (16)

Cl1—C3	1.732 (2)	C11—H11A	0.9300
Cl2—C5	1.732 (2)	C12—C13	1.469 (2)
O1—C7	1.219 (2)	C13—C18	1.385 (2)
O2—C16	1.375 (2)	C13—C14	1.395 (3)
O2—C19	1.420 (3)	C14—C15	1.374 (3)
N1—C11	1.346 (2)	C14—H14A	0.9300
N1—N2	1.3652 (19)	C15—C16	1.378 (3)
N1—C20	1.423 (2)	C15—H15A	0.9300
N2—C12	1.329 (2)	C16—C17	1.372 (3)
C1—C2	1.377 (3)	C17—C18	1.386 (3)
C1—C6	1.387 (3)	C17—H17A	0.9300
C1—H1A	0.9300	C18—H18A	0.9300
C2—C3	1.367 (4)	C20—C25	1.371 (3)
C2—H2A	0.9300	C20—C21	1.372 (3)
C3—C4	1.367 (4)	C21—C22	1.373 (3)
C4—C5	1.377 (3)	C21—H21A	0.9300
C4—H4A	0.9300	C22—C23	1.370 (4)
C5—C6	1.390 (3)	C22—H22A	0.9300
C6—C7	1.502 (3)	C23—C24	1.361 (4)
C7—C8	1.456 (3)	C23—H23A	0.9300
C8—C9	1.331 (2)	C24—C25	1.384 (3)
C8—H8A	0.9300	C24—H24A	0.9300
C9—C10	1.446 (2)	C25—H25A	0.9300
C9—H9A	0.9300	C19—H19A	0.9600
C10—C11	1.373 (2)	C19—H19B	0.9600
C10—C12	1.418 (2)	C19—H19C	0.9600
C16—O2—C19	117.41 (19)	C18—C13—C12	121.17 (15)
C11—N1—N2	111.97 (14)	C14—C13—C12	121.21 (16)
C11—N1—C20	128.54 (15)	C15—C14—C13	120.91 (19)
N2—N1—C20	119.37 (14)	C15—C14—H14A	119.5
C12—N2—N1	104.76 (14)	C13—C14—H14A	119.5
C2—C1—C6	122.08 (19)	C14—C15—C16	120.39 (18)
C2—C1—H1A	119.0	C14—C15—H15A	119.8
C6—C1—H1A	119.0	C16—C15—H15A	119.8
C3—C2—C1	118.6 (2)	C17—C16—O2	124.4 (2)
C3—C2—H2A	120.7	C17—C16—C15	119.95 (18)
C1—C2—H2A	120.7	O2—C16—C15	115.61 (19)
C2—C3—C4	121.7 (2)	C16—C17—C18	119.53 (19)
C2—C3—Cl1	119.7 (2)	C16—C17—H17A	120.2
C4—C3—Cl1	118.7 (2)	C18—C17—H17A	120.2
C3—C4—C5	118.9 (2)	C13—C18—C17	121.60 (17)
C3—C4—H4A	120.5	C13—C18—H18A	119.2
C5—C4—H4A	120.5	C17—C18—H18A	119.2
C4—C5—C6	121.7 (2)	C25—C20—C21	120.49 (19)
C4—C5—Cl2	117.99 (17)	C25—C20—N1	119.80 (17)
C6—C5—Cl2	120.32 (16)	C21—C20—N1	119.71 (18)
C1—C6—C5	117.05 (17)	C20—C21—C22	119.0 (2)
C1—C6—C7	120.06 (16)	C20—C21—H21A	120.5
C5—C6—C7	122.85 (17)	C22—C21—H21A	120.5
O1—C7—C8	121.38 (17)	C23—C22—C21	121.0 (3)
O1—C7—C6	119.50 (17)	C23—C22—H22A	119.5
C8—C7—C6	119.10 (16)	C21—C22—H22A	119.5
C9—C8—C7	124.68 (17)	C24—C23—C22	119.7 (2)
C9—C8—H8A	117.7	C24—C23—H23A	120.1
C7—C8—H8A	117.7	C22—C23—H23A	120.1
C8—C9—C10	126.51 (16)	C23—C24—C25	120.1 (2)
C8—C9—H9A	116.7	C23—C24—H24A	120.0
C10—C9—H9A	116.7	C25—C24—H24A	120.0
C11—C10—C12	104.58 (15)	C20—C25—C24	119.6 (2)
C11—C10—C9	128.28 (16)	C20—C25—H25A	120.2
C12—C10—C9	127.08 (15)	C24—C25—H25A	120.2
N1—C11—C10	107.42 (15)	O2—C19—H19A	109.5
N1—C11—H11A	126.3	O2—C19—H19B	109.5
C10—C11—H11A	126.3	H19A—C19—H19B	109.5
N2—C12—C10	111.27 (15)	O2—C19—H19C	109.5
N2—C12—C13	120.38 (15)	H19A—C19—H19C	109.5
C10—C12—C13	128.34 (15)	H19B—C19—H19C	109.5
C18—C13—C14	117.61 (16)
C11—N1—N2—C12	−0.55 (19)	C9—C10—C12—N2	−178.05 (16)
C20—N1—N2—C12	−176.84 (15)	C11—C10—C12—C13	−179.56 (17)
C6—C1—C2—C3	−0.1 (4)	C9—C10—C12—C13	3.1 (3)
C1—C2—C3—C4	0.4 (4)	N2—C12—C13—C18	40.9 (2)
C1—C2—C3—Cl1	−179.74 (18)	C10—C12—C13—C18	−140.33 (19)
C2—C3—C4—C5	−0.5 (4)	N2—C12—C13—C14	−137.87 (19)
Cl1—C3—C4—C5	179.7 (2)	C10—C12—C13—C14	40.9 (3)
C3—C4—C5—C6	0.1 (4)	C18—C13—C14—C15	1.0 (3)
C3—C4—C5—Cl2	−178.0 (2)	C12—C13—C14—C15	179.78 (18)
C2—C1—C6—C5	−0.3 (3)	C13—C14—C15—C16	−0.1 (3)
C2—C1—C6—C7	−178.16 (19)	C19—O2—C16—C17	2.7 (3)
C4—C5—C6—C1	0.2 (3)	C19—O2—C16—C15	−177.7 (2)
Cl2—C5—C6—C1	178.28 (15)	C14—C15—C16—C17	−0.9 (3)
C4—C5—C6—C7	178.1 (2)	C14—C15—C16—O2	179.47 (19)
Cl2—C5—C6—C7	−3.9 (3)	O2—C16—C17—C18	−179.4 (2)
C1—C6—C7—O1	125.1 (2)	C15—C16—C17—C18	1.0 (3)
C5—C6—C7—O1	−52.7 (3)	C14—C13—C18—C17	−0.9 (3)
C1—C6—C7—C8	−53.7 (3)	C12—C13—C18—C17	−179.66 (17)
C5—C6—C7—C8	128.5 (2)	C16—C17—C18—C13	−0.1 (3)
O1—C7—C8—C9	169.9 (2)	C11—N1—C20—C25	174.64 (19)
C6—C7—C8—C9	−11.3 (3)	N2—N1—C20—C25	−9.8 (3)
C7—C8—C9—C10	−178.89 (18)	C11—N1—C20—C21	−5.1 (3)
C8—C9—C10—C11	19.4 (3)	N2—N1—C20—C21	170.51 (18)
C8—C9—C10—C12	−163.87 (19)	C25—C20—C21—C22	0.9 (4)
N2—N1—C11—C10	0.1 (2)	N1—C20—C21—C22	−179.4 (2)
C20—N1—C11—C10	175.99 (17)	C20—C21—C22—C23	0.1 (4)
C12—C10—C11—N1	0.32 (19)	C21—C22—C23—C24	0.0 (5)
C9—C10—C11—N1	177.64 (17)	C22—C23—C24—C25	−1.1 (4)
N1—N2—C12—C10	0.75 (19)	C21—C20—C25—C24	−2.0 (3)
N1—N2—C12—C13	179.72 (15)	N1—C20—C25—C24	178.3 (2)
C11—C10—C12—N2	−0.7 (2)	C23—C24—C25—C20	2.1 (4)

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11A···O1i	0.93	2.35	3.271 (2)	171

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C11—H11A⋯O1i	0.93	2.35	3.271 (2)	171

Symmetry code: (i) .