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

Isloor, A.M.; Malladi, S.; Gerber, T.; Brecht, B. van; Betz, R.

doi:10.1107/S1600536812003960

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 68| Part 3| March 2012| Pages o616-o617

doi:10.1107/S1600536812003960

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

Arun M. Isloor,^a Shridhar Malladi,^a Thomas Gerber,^b Benjamin van Brecht ^b and Richard Betz ^b ^*

^aOrganic Electronics Division, Department of Chemistry, National Institute of Technology - Karnataka, Surathkal, Mangalore 575 025, India, and ^bNelson Mandela Metropolitan University, Summerstrand Campus, Department of Chemistry, University Way, Summerstrand, PO Box 77000, Port Elizabeth 6031, South Africa
^*Correspondence e-mail: richard.betz@webmail.co.za

(Received 18 January 2012; accepted 30 January 2012; online 4 February 2012)

In the title compound, C₂₄H₁₅Cl₂N₃O₃, 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 intercentroid distance between two aromatic systems is 3.5455 (7) Å and is apparent between two pyrazole systems. Further π–π interactions are manifest between a pair of 4-nitrophenyl rings [centroid-to-centroid distance = 3.6443 (7) Å] and a pair of 2,4-dichlorophenyl 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_r = 464.29
Triclinic, $[P \overline 1]$
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[F² > 2σ(F²)] = 0.030
wR(F²) = 0.086
S = 1.02
5116 reflections
304 parameters
H-atom parameters constrained
Δρ_max = 0.36 e Å⁻³
Δρ_min = −0.21 e Å⁻³

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

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 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812003960/su2371sup1.cif

Supporting information file. DOI: 10.1107/S1600536812003960/su2371Isup2.cdx

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

Supporting information file. DOI: 10.1107/S1600536812003960/su2371Isup4.cml

checkCIF report

Comment top

The pyrazole ring is an important structural motif found in several pharmaceutically active compounds. Because of its easy preparation and rich biological activity, the pyrazole skeleton plays an important role in biologically active compounds such as antibacterial (Isloor et al., 2009; Vijesh et al., 2010), anti-inflammatory (Sharma et al., 2010), analgesic (Rostom et al., 2003), anticancer, radioprotective (Ghorab et al., 2010) and anti-convulsant agents (Amnekar & Bhusari, 2010). Prompted by the diverse activities of pyrazole derivatives, we have synthesized the title compound to study its crystal structure.

In the title compound the C═C double bond in the Michael system adopts (E)-configuration (Fig. 1). The 1-phenyl-1H-pyrazole moiety is essentially planar (r.m.s. deviation of all fitted non-hydrogen atoms = 0.0780 Å). However, the mean planes of the two components are inclined at an angle of 9.95 (7)°.

The N-bonded phenyl ring B (C21–C26), the 4-nitrophenyl ring C (C11–C16), and the 2,4-dichlorophenyl ring D (C31–C36) are inclined to the mean plane of the central heterocyclic five-membered ring A (N1,N2,C4–C6) by 9.95 (7), 24.54 (6) and 43.06 (6) °, respectively. The mean planes defined the phenyl rings (B, C and D) are inclined to one another by angles of B/C = 16.28 (6)°, C/D = 28.40 (6)° and B/D = 40.14 (6)°.

In the crystal, C—H···O contacts whose range falls by more than 0.3 Å below the sum of van der Waals radii of the corresponding atoms are present. They are supported by one of the H atoms of the pyrazole system on the one hand and one of the H atoms on the dichlorophenyl moiety on the other hand. While the former of these contacts applies exclusively to one of the O atoms (O1) on the nitro group as acceptor, the latter ones are apparent in conjunction with the O atom (O3) on the Michael system (Table 1 and Fig. 2). In terms of graph-set analysis (Etter et al., 1990; Bernstein et al., 1995), the descriptor for the C—H···O contacts is C¹₁(11)R²₂(10) on the unitary level.

The shortest intercentroid distance between two aromatic systems is 3.5455 (7) Å involving inversion related pyrazole systems [CgA···CgAⁱ]. Further π–π interactions are manifest between inversion related 4-nitrophenyl rings (CgC···CgCⁱⁱ = 3.6443 (7) Å) and inversion related 2,4-dichlorophenyl rings (CgD···CgDⁱⁱⁱ = 3.7797 (7) Å) [symmetry codes: (i) -x + 2, -y + 1, -z + 1; (ii) -x + 2, -y + 2, -z + 1; (iii) -x + 1, -y, -z].

In total, the molecules are connected into a double layer two-dimensional network lying parallel to plane (110) [Fig. 3].

Related literature top

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 top

To a cold, stirred mixture of methanol (20 ml) and sodium hydroxide (12.09 mmol) was added 2,4-dichloroacetophenone (4.03 mmol). The reaction mixture was stirred for 10 min. To this was added 3-(4-nitrophenyl)-1-phenyl-1H-pyrazole-4-carbaldehyde (4.03 mmol) followed by tetrahydrofuran (30 ml). The solution was further stirred at 0°C for 2 h and then at room temperature for 5 h. It was then poured into ice cold water. The resulting solution was neutralized with diluted hydrochloric acid. The solid that separated was filtered, washed with water, dried and crystallized from ethanol. Yield: 1.48 g, 79.39% (m.p. 478–480 K).

Computing details top

Data collection: APEX2 (Bruker, 2010); cell refinement: SAINT (Bruker, 2010); data reduction: SAINT (Bruker, 2010); 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 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound, with atom labels and displacement ellipsoids drawn at the 50% probability level.
	Fig. 2. A partial view along the a axis of the crystal packing of the title compound, showing the C—H···O intermolecular contacts [Symmetry operators: (i) x - 1, y - 1, z; (ii) x + 1, y + 1, z; (iii) -x + 1, -y + 1, -z].
	Fig. 3. A view along the a axis of the crystal packing of the title compound (displacement ellipsoids are drawn at 50% probability level).

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

Crystal data top

C₂₄H₁₅Cl₂N₃O₃	Z = 2
M_r = 464.29	F(000) = 476
Triclinic, P1	D_x = 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

Data collection top

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

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)] = 0.030	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.086	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.046P)² + 0.3579P] where P = (F_o² + 2F_c²)/3
5116 reflections	(Δ/σ)_max = 0.001
304 parameters	Δρ_max = 0.36 e Å⁻³
0 restraints	Δρ_min = −0.21 e Å⁻³

Crystal data top

C₂₄H₁₅Cl₂N₃O₃	γ = 96.060 (2)°
M_r = 464.29	V = 1032.12 (7) Å³
Triclinic, P1	Z = 2
a = 8.3343 (3) Å	Mo Kα radiation
b = 9.3115 (4) Å	µ = 0.35 mm⁻¹
c = 13.8699 (6) Å	T = 200 K
α = 92.896 (2)°	0.53 × 0.30 × 0.13 mm
β = 104.669 (2)°

Data collection top

Bruker APEXII CCD diffractometer	5116 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2008)	4588 reflections with I > 2σ(I)
T_min = 0.931, T_max = 1.000	R_int = 0.013
18344 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.030	0 restraints
wR(F²) = 0.086	H-atom parameters constrained
S = 1.02	Δρ_max = 0.36 e Å⁻³
5116 reflections	Δρ_min = −0.21 e Å⁻³
304 parameters

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

	x	y	z	U_iso*/U_eq
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)*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) x−1, y−1, z; (ii) −x+1, −y+1, −z.

Experimental details

Crystal data
Chemical formula	C₂₄H₁₅Cl₂N₃O₃
M_r	464.29
Crystal system, space group	Triclinic, P1
Temperature (K)	200
a, b, c (Å)	8.3343 (3), 9.3115 (4), 13.8699 (6)
α, β, γ (°)	92.896 (2), 104.669 (2), 96.060 (2)
V (Å³)	1032.12 (7)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.35
Crystal size (mm)	0.53 × 0.30 × 0.13

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2008)
T_min, T_max	0.931, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	18344, 5116, 4588
R_int	0.013
(sin θ/λ)_max (Å⁻¹)	0.668

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.030, 0.086, 1.02
No. of reflections	5116
No. of parameters	304
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.36, −0.21

Computer programs: APEX2 (Bruker, 2010), SAINT (Bruker, 2010), SHELXS97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2008), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O1ⁱ	0.95	2.39	3.3421 (14)	175.8
C36—H36···O3ⁱⁱ	0.95	2.41	3.3139 (15)	159.8

Symmetry codes: (i) x−1, y−1, z; (ii) −x+1, −y+1, −z.

Acknowledgements

AMI is grateful to the Department of Atomic Energy, Board for Research in Nuclear Sciences, Government of India, for a Young Scientist award.

References

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Volume 68| Part 3| March 2012| Pages o616-o617

doi:10.1107/S1600536812003960

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

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

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Experimental

Crystal data

Data collection

Refinement

Supporting information

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References

organic compounds

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