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

In the title compound, C(24)H(15)Cl(2)N(3)O(3), the C=C double bond is E configured. The 1-phenyl-1H-pyrazole moiety is roughly planar (r.m.s. deviation of all fitted non-H atoms = 0.0780 Å), but the mean planes of the two components are inclined at an angle of 9.95 (7)°. The mean plane defined by the non-H atoms of the 1H-pyrazole ring encloses angles of 9.95 (7), 24.54 (6) and 43.02 (6)° with the mean planes of the different benzene rings. In the crystal, C-H⋯O contacts are present and result in the formation of a double-layer two-dimensional network lying parallel to (110). The shortest inter-centroid distance between two aromatic systems is 3.5455 (7) Å and is apparent between two pyrazole systems. Further π-π inter-actions are manifest between a pair of 4-nitro-phenyl rings [centroid-to-centroid distance = 3.6443 (7) Å] and a pair of 2,4-dichloro-phenyl rings [centroid-to-centroid distance = 3.7797 (7) Å].

Related literature

For general background on the pharmaceutical and biological activity of pyrazole compounds, see: Isloor et al. (2009 ▶); Vijesh et al. (2010 ▶); Sharma et al. (2010 ▶); Rostom et al. (2003 ▶); Ghorab et al. (2010 ▶); Amnekar & Bhusari (2010 ▶). For graph-set analysis of hydrogen bonds, see: Etter et al. (1990 ▶); Bernstein et al. (1995 ▶).

Experimental

Crystal data

C24H15Cl2N3O3

M = 464.29

Triclinic,

a = 8.3343 (3) Å

b = 9.3115 (4) Å

c = 13.8699 (6) Å

α = 92.896 (2)°

β = 104.669 (2)°

γ = 96.060 (2)°

V = 1032.12 (7) Å3

Z = 2

Mo Kα radiation

μ = 0.35 mm−1

T = 200 K

0.53 × 0.30 × 0.13 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.931, T max = 1.000

18344 measured reflections

5116 independent reflections

4588 reflections with I > 2σ(I)

R int = 0.013

Refinement

R[F 2 > 2σ(F 2)] = 0.030

wR(F 2) = 0.086

S = 1.02

5116 reflections

304 parameters

H-atom parameters constrained

Δρmax = 0.36 e Å−3

Δρmin = −0.21 e Å−3

Data collection: APEX2 (Bruker, 2010 ▶); cell refinement: SAINT (Bruker, 2010 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812003960/su2371sup1.cif

Supplementary material file. DOI: 10.1107/S1600536812003960/su2371Isup2.cdx

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812003960/su2371Isup3.hkl

Supplementary material file. DOI: 10.1107/S1600536812003960/su2371Isup4.cml

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

C24H15Cl2N3O3	Z = 2
Mr = 464.29	F(000) = 476
Triclinic, P1	Dx = 1.494 Mg m−3
Hall symbol: -P 1	Melting point = 478–480 K
a = 8.3343 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.3115 (4) Å	Cell parameters from 9938 reflections
c = 13.8699 (6) Å	θ = 2.6–28.3°
α = 92.896 (2)°	µ = 0.35 mm−1
β = 104.669 (2)°	T = 200 K
γ = 96.060 (2)°	Plate, yellow
V = 1032.12 (7) Å3	0.53 × 0.30 × 0.13 mm

Bruker APEXII CCD diffractometer	5116 independent reflections
Radiation source: fine-focus sealed tube	4588 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.013
φ and ω scans	θmax = 28.4°, θmin = 1.5°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −11→11
Tmin = 0.931, Tmax = 1.000	k = −11→12
18344 measured reflections	l = −18→18

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)] = 0.030	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.086	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.046P)2 + 0.3579P] where P = (Fo2 + 2Fc2)/3
5116 reflections	(Δ/σ)max = 0.001
304 parameters	Δρmax = 0.36 e Å−3
0 restraints	Δρmin = −0.21 e Å−3

	x	y	z	Uiso*/Ueq
Cl1	0.61554 (4)	0.04973 (3)	0.23425 (2)	0.03315 (9)
Cl2	0.09111 (4)	−0.11303 (4)	−0.07809 (2)	0.03888 (9)
O1	1.42080 (12)	1.17926 (10)	0.43746 (8)	0.0407 (2)
O2	1.27245 (13)	1.14934 (11)	0.28397 (7)	0.0398 (2)
O3	0.69233 (12)	0.43425 (10)	0.10434 (6)	0.0350 (2)
N1	0.78730 (12)	0.53362 (9)	0.57632 (7)	0.02186 (18)
N2	0.89358 (12)	0.65279 (10)	0.57207 (7)	0.02233 (18)
N3	1.30319 (13)	1.11802 (11)	0.37064 (8)	0.0286 (2)
C1	0.61545 (15)	0.35986 (12)	0.15177 (8)	0.0248 (2)
C2	0.63269 (15)	0.39188 (12)	0.25920 (8)	0.0256 (2)
H2	0.5617	0.3378	0.2917	0.029 (4)*
C3	0.74872 (14)	0.49747 (12)	0.31106 (8)	0.0238 (2)
H3	0.8177	0.5483	0.2758	0.030 (4)*
C4	0.77783 (13)	0.54064 (11)	0.41643 (8)	0.0219 (2)
C5	0.71502 (14)	0.46538 (11)	0.48506 (8)	0.0233 (2)
H5	0.6355	0.3811	0.4706	0.034 (4)*
C6	0.88826 (13)	0.65830 (11)	0.47531 (8)	0.0205 (2)
C11	0.99209 (13)	0.77692 (11)	0.44612 (8)	0.0206 (2)
C12	0.95250 (15)	0.82678 (12)	0.35047 (8)	0.0261 (2)
H12	0.8545	0.7837	0.3022	0.035 (4)*
C13	1.05435 (15)	0.93829 (12)	0.32506 (8)	0.0271 (2)
H13	1.0283	0.9710	0.2597	0.039 (4)*
C14	1.19461 (13)	1.00064 (11)	0.39712 (8)	0.0236 (2)
C15	1.23561 (14)	0.95718 (12)	0.49328 (8)	0.0252 (2)
H15	1.3312	1.0037	0.5419	0.038 (4)*
C16	1.13429 (14)	0.84452 (12)	0.51712 (8)	0.0239 (2)
H16	1.1616	0.8126	0.5826	0.030 (4)*
C21	0.77030 (14)	0.49032 (12)	0.67088 (8)	0.0240 (2)
C22	0.87694 (18)	0.55949 (14)	0.75788 (9)	0.0331 (3)
H22	0.9608	0.6352	0.7548	0.043 (4)*
C23	0.8601 (2)	0.51708 (15)	0.84967 (10)	0.0414 (3)
H23	0.9330	0.5642	0.9096	0.054 (5)*
C24	0.7381 (2)	0.40681 (15)	0.85476 (10)	0.0414 (3)
H24	0.7266	0.3784	0.9177	0.054 (5)*
C25	0.63317 (19)	0.33854 (16)	0.76723 (11)	0.0403 (3)
H25	0.5493	0.2629	0.7705	0.056 (5)*
C26	0.64836 (16)	0.37876 (14)	0.67454 (9)	0.0322 (3)
H26	0.5764	0.3307	0.6147	0.046 (5)*
C31	0.48885 (14)	0.23647 (12)	0.09753 (8)	0.0237 (2)
C32	0.47465 (14)	0.09718 (12)	0.12861 (8)	0.0240 (2)
C33	0.35401 (15)	−0.01128 (12)	0.07491 (8)	0.0271 (2)
H33	0.3472	−0.1063	0.0968	0.040 (4)*
C34	0.24377 (15)	0.02196 (13)	−0.01124 (8)	0.0277 (2)
C35	0.25331 (16)	0.15887 (14)	−0.04498 (9)	0.0315 (3)
H35	0.1762	0.1799	−0.1043	0.045 (4)*
C36	0.37677 (16)	0.26473 (13)	0.00889 (8)	0.0292 (2)
H36	0.3857	0.3585	−0.0147	0.034 (4)*

	U11	U22	U33	U12	U13	U23
Cl1	0.04021 (17)	0.02982 (15)	0.02282 (14)	0.00229 (11)	−0.00347 (11)	0.00416 (10)
Cl2	0.03790 (17)	0.03595 (17)	0.03315 (16)	−0.01017 (13)	−0.00076 (12)	−0.00578 (12)
O1	0.0281 (4)	0.0329 (5)	0.0548 (6)	−0.0099 (4)	0.0046 (4)	0.0044 (4)
O2	0.0452 (5)	0.0380 (5)	0.0402 (5)	−0.0023 (4)	0.0201 (4)	0.0115 (4)
O3	0.0458 (5)	0.0326 (4)	0.0242 (4)	−0.0089 (4)	0.0100 (4)	0.0028 (3)
N1	0.0256 (4)	0.0183 (4)	0.0212 (4)	−0.0012 (3)	0.0069 (3)	0.0010 (3)
N2	0.0257 (4)	0.0182 (4)	0.0214 (4)	−0.0023 (3)	0.0052 (3)	0.0006 (3)
N3	0.0259 (5)	0.0227 (4)	0.0393 (6)	0.0001 (4)	0.0131 (4)	0.0039 (4)
C1	0.0310 (5)	0.0209 (5)	0.0199 (5)	−0.0009 (4)	0.0040 (4)	−0.0003 (4)
C2	0.0306 (5)	0.0241 (5)	0.0205 (5)	−0.0032 (4)	0.0067 (4)	−0.0015 (4)
C3	0.0284 (5)	0.0207 (5)	0.0211 (5)	−0.0016 (4)	0.0064 (4)	−0.0006 (4)
C4	0.0232 (5)	0.0192 (5)	0.0215 (5)	−0.0013 (4)	0.0045 (4)	−0.0009 (4)
C5	0.0254 (5)	0.0195 (5)	0.0232 (5)	−0.0020 (4)	0.0055 (4)	−0.0010 (4)
C6	0.0219 (5)	0.0183 (4)	0.0198 (5)	0.0003 (4)	0.0040 (4)	0.0000 (4)
C11	0.0225 (5)	0.0175 (4)	0.0205 (5)	−0.0005 (4)	0.0044 (4)	−0.0003 (4)
C12	0.0281 (5)	0.0246 (5)	0.0204 (5)	−0.0048 (4)	0.0006 (4)	0.0010 (4)
C13	0.0322 (6)	0.0259 (5)	0.0207 (5)	−0.0029 (4)	0.0046 (4)	0.0039 (4)
C14	0.0232 (5)	0.0191 (5)	0.0288 (5)	−0.0010 (4)	0.0091 (4)	0.0016 (4)
C15	0.0231 (5)	0.0222 (5)	0.0263 (5)	−0.0016 (4)	0.0010 (4)	−0.0004 (4)
C16	0.0260 (5)	0.0223 (5)	0.0201 (5)	−0.0004 (4)	0.0012 (4)	0.0008 (4)
C21	0.0295 (5)	0.0216 (5)	0.0222 (5)	0.0038 (4)	0.0087 (4)	0.0041 (4)
C22	0.0443 (7)	0.0281 (6)	0.0249 (6)	−0.0043 (5)	0.0092 (5)	0.0008 (4)
C23	0.0618 (9)	0.0359 (7)	0.0228 (6)	−0.0046 (6)	0.0087 (6)	0.0018 (5)
C24	0.0604 (9)	0.0387 (7)	0.0279 (6)	0.0023 (6)	0.0167 (6)	0.0108 (5)
C25	0.0454 (8)	0.0393 (7)	0.0369 (7)	−0.0044 (6)	0.0135 (6)	0.0149 (6)
C26	0.0349 (6)	0.0311 (6)	0.0283 (6)	−0.0030 (5)	0.0062 (5)	0.0073 (5)
C31	0.0304 (5)	0.0217 (5)	0.0169 (5)	−0.0009 (4)	0.0048 (4)	−0.0010 (4)
C32	0.0290 (5)	0.0245 (5)	0.0165 (4)	0.0015 (4)	0.0030 (4)	0.0011 (4)
C33	0.0332 (6)	0.0223 (5)	0.0233 (5)	−0.0012 (4)	0.0050 (4)	0.0012 (4)
C34	0.0291 (5)	0.0274 (5)	0.0225 (5)	−0.0026 (4)	0.0032 (4)	−0.0042 (4)
C35	0.0361 (6)	0.0319 (6)	0.0205 (5)	0.0018 (5)	−0.0023 (4)	0.0009 (4)
C36	0.0398 (6)	0.0233 (5)	0.0209 (5)	0.0013 (5)	0.0022 (5)	0.0030 (4)

Cl1—C32	1.7391 (11)	C13—H13	0.9500
Cl2—C34	1.7336 (11)	C14—C15	1.3829 (16)
O1—N3	1.2302 (14)	C15—C16	1.3829 (15)
O2—N3	1.2210 (14)	C15—H15	0.9500
O3—C1	1.2203 (14)	C16—H16	0.9500
N1—C5	1.3493 (14)	C21—C22	1.3850 (16)
N1—N2	1.3582 (12)	C21—C26	1.3868 (16)
N1—C21	1.4277 (13)	C22—C23	1.3878 (17)
N2—C6	1.3354 (14)	C22—H22	0.9500
N3—C14	1.4657 (14)	C23—C24	1.384 (2)
C1—C2	1.4722 (15)	C23—H23	0.9500
C1—C31	1.5014 (15)	C24—C25	1.382 (2)
C2—C3	1.3397 (15)	C24—H24	0.9500
C2—H2	0.9500	C25—C26	1.3892 (17)
C3—C4	1.4481 (14)	C25—H25	0.9500
C3—H3	0.9500	C26—H26	0.9500
C4—C5	1.3832 (15)	C31—C32	1.3899 (15)
C4—C6	1.4248 (14)	C31—C36	1.3986 (16)
C5—H5	0.9500	C32—C33	1.3842 (15)
C6—C11	1.4675 (14)	C33—C34	1.3817 (16)
C11—C12	1.3990 (15)	C33—H33	0.9500
C11—C16	1.3998 (14)	C34—C35	1.3815 (17)
C12—C13	1.3875 (15)	C35—C36	1.3823 (16)
C12—H12	0.9500	C35—H35	0.9500
C13—C14	1.3815 (16)	C36—H36	0.9500
C5—N1—N2	112.12 (9)	C15—C16—C11	120.93 (10)
C5—N1—C21	127.88 (9)	C15—C16—H16	119.5
N2—N1—C21	119.91 (9)	C11—C16—H16	119.5
C6—N2—N1	105.11 (8)	C22—C21—C26	120.80 (11)
O2—N3—O1	123.73 (10)	C22—C21—N1	119.53 (10)
O2—N3—C14	118.48 (10)	C26—C21—N1	119.66 (10)
O1—N3—C14	117.79 (10)	C21—C22—C23	119.37 (12)
O3—C1—C2	122.78 (10)	C21—C22—H22	120.3
O3—C1—C31	118.98 (10)	C23—C22—H22	120.3
C2—C1—C31	118.10 (10)	C24—C23—C22	120.62 (13)
C3—C2—C1	119.88 (10)	C24—C23—H23	119.7
C3—C2—H2	120.1	C22—C23—H23	119.7
C1—C2—H2	120.1	C25—C24—C23	119.27 (12)
C2—C3—C4	125.46 (10)	C25—C24—H24	120.4
C2—C3—H3	117.3	C23—C24—H24	120.4
C4—C3—H3	117.3	C24—C25—C26	121.08 (12)
C5—C4—C6	104.13 (9)	C24—C25—H25	119.5
C5—C4—C3	126.45 (10)	C26—C25—H25	119.5
C6—C4—C3	129.11 (10)	C21—C26—C25	118.86 (12)
N1—C5—C4	107.48 (9)	C21—C26—H26	120.6
N1—C5—H5	126.3	C25—C26—H26	120.6
C4—C5—H5	126.3	C32—C31—C36	117.80 (10)
N2—C6—C4	111.14 (9)	C32—C31—C1	125.11 (10)
N2—C6—C11	118.25 (9)	C36—C31—C1	117.09 (10)
C4—C6—C11	130.60 (9)	C33—C32—C31	121.95 (10)
C12—C11—C16	118.75 (10)	C33—C32—Cl1	117.05 (9)
C12—C11—C6	122.43 (9)	C31—C32—Cl1	120.93 (8)
C16—C11—C6	118.82 (9)	C34—C33—C32	118.38 (10)
C13—C12—C11	120.93 (10)	C34—C33—H33	120.8
C13—C12—H12	119.5	C32—C33—H33	120.8
C11—C12—H12	119.5	C35—C34—C33	121.64 (11)
C14—C13—C12	118.35 (10)	C35—C34—Cl2	119.80 (9)
C14—C13—H13	120.8	C33—C34—Cl2	118.57 (9)
C12—C13—H13	120.8	C34—C35—C36	118.94 (11)
C13—C14—C15	122.50 (10)	C34—C35—H35	120.5
C13—C14—N3	118.63 (10)	C36—C35—H35	120.5
C15—C14—N3	118.87 (10)	C35—C36—C31	121.26 (11)
C14—C15—C16	118.51 (10)	C35—C36—H36	119.4
C14—C15—H15	120.7	C31—C36—H36	119.4
C16—C15—H15	120.7
C5—N1—N2—C6	−0.46 (12)	C14—C15—C16—C11	−0.82 (17)
C21—N1—N2—C6	176.30 (9)	C12—C11—C16—C15	−0.90 (17)
O3—C1—C2—C3	−6.97 (19)	C6—C11—C16—C15	−179.72 (10)
C31—C1—C2—C3	177.41 (11)	C5—N1—C21—C22	168.36 (12)
C1—C2—C3—C4	179.47 (11)	N2—N1—C21—C22	−7.84 (16)
C2—C3—C4—C5	12.94 (19)	C5—N1—C21—C26	−11.06 (17)
C2—C3—C4—C6	−174.38 (12)	N2—N1—C21—C26	172.74 (10)
N2—N1—C5—C4	1.10 (13)	C26—C21—C22—C23	−0.6 (2)
C21—N1—C5—C4	−175.35 (10)	N1—C21—C22—C23	−179.98 (12)
C6—C4—C5—N1	−1.21 (12)	C21—C22—C23—C24	0.0 (2)
C3—C4—C5—N1	172.94 (10)	C22—C23—C24—C25	0.3 (2)
N1—N2—C6—C4	−0.35 (12)	C23—C24—C25—C26	0.0 (2)
N1—N2—C6—C11	−179.79 (9)	C22—C21—C26—C25	0.87 (19)
C5—C4—C6—N2	0.98 (12)	N1—C21—C26—C25	−179.71 (12)
C3—C4—C6—N2	−172.95 (11)	C24—C25—C26—C21	−0.6 (2)
C5—C4—C6—C11	−179.66 (11)	O3—C1—C31—C32	133.57 (13)
C3—C4—C6—C11	6.41 (19)	C2—C1—C31—C32	−50.63 (16)
N2—C6—C11—C12	−154.77 (11)	O3—C1—C31—C36	−46.48 (16)
C4—C6—C11—C12	25.91 (18)	C2—C1—C31—C36	129.32 (12)
N2—C6—C11—C16	24.00 (15)	C36—C31—C32—C33	−0.28 (17)
C4—C6—C11—C16	−155.32 (11)	C1—C31—C32—C33	179.67 (11)
C16—C11—C12—C13	1.85 (17)	C36—C31—C32—Cl1	176.56 (9)
C6—C11—C12—C13	−179.37 (11)	C1—C31—C32—Cl1	−3.49 (16)
C11—C12—C13—C14	−1.05 (18)	C31—C32—C33—C34	−0.93 (18)
C12—C13—C14—C15	−0.76 (18)	Cl1—C32—C33—C34	−177.88 (9)
C12—C13—C14—N3	179.71 (10)	C32—C33—C34—C35	0.97 (18)
O2—N3—C14—C13	−5.21 (16)	C32—C33—C34—Cl2	−179.36 (9)
O1—N3—C14—C13	174.93 (11)	C33—C34—C35—C36	0.21 (19)
O2—N3—C14—C15	175.23 (11)	Cl2—C34—C35—C36	−179.46 (10)
O1—N3—C14—C15	−4.62 (16)	C34—C35—C36—C31	−1.5 (2)
C13—C14—C15—C16	1.68 (17)	C32—C31—C36—C35	1.50 (18)
N3—C14—C15—C16	−178.78 (10)	C1—C31—C36—C35	−178.46 (11)

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O1i	0.95	2.39	3.3421 (14)	176
C36—H36···O3ii	0.95	2.41	3.3139 (15)	160

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5⋯O1i	0.95	2.39	3.3421 (14)	176
C36—H36⋯O3ii	0.95	2.41	3.3139 (15)	160

Symmetry codes: (i) ; (ii) .