3-[(E)-3-(4-Meth­oxy­phen­yl)prop-2-eno­yl]-1-(4-methyl­phen­yl)-5-phenyl-1H-pyrazole-4-carbonitrile

Abdel-Aziz, H.A.; Bari, A.; Ng, S.W.

doi:10.1107/S1600536811005770

organic compounds

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ISSN: 2056-9890

Volume 67| Part 3| March 2011| Page o694

doi:10.1107/S1600536811005770

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3-[(E)-3-(4-Methoxyphenyl)prop-2-enoyl]-1-(4-methylphenyl)-5-phenyl-1H-pyrazole-4-carbonitrile

Hatem A. Abdel-Aziz,^a Ahmed Bari ^a and Seik Weng Ng ^b ^*

^aDepartment of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, Riyadh 11451, Saudi Arabia, and ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 14 February 2011; accepted 16 February 2011; online 23 February 2011)

In the title compound, C₂₇H₂₁N₃O₂, the non-H atoms of the methoxyphenylacryloyl substitutent of the pyrazolyl ring are almost co-planar (r.m.s. deviation = 0.070 Å), and the mean plane is twisted by 18.7 (1)° with respect to the pyrazolyl ring. The phenyl and tolyl substituents are aligned at 48.9 (1) and 44.5 (1)° with respect to the pyrazolyl ring. Weak intermolecular C—H⋯O and C—H⋯N hydrogen bonding is present in the crystal structure.

Related literature

For background to the biological properties of aryl-substituted pyrazoles, see: Abdel-Aziz et al. (2010 , 2011 ).

Experimental

Crystal data

C₂₇H₂₁N₃O₂
M_r = 419.47
Triclinic, $[P \overline 1]$
a = 10.9995 (7) Å
b = 11.0531 (8) Å
c = 11.4381 (8) Å
α = 95.113 (6)°
β = 111.582 (6)°
γ = 118.219 (7)°
V = 1079.13 (18) Å³
Z = 2
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 100 K
0.20 × 0.15 × 0.05 mm

Data collection

Agilent SuperNova Dual diffractometer with Atlas detector
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010 ) T_min = 0.984, T_max = 0.996
8250 measured reflections
4779 independent reflections
3346 reflections with I > 2σ(I)
R_int = 0.033

Refinement

R[F² > 2σ(F²)] = 0.053
wR(F²) = 0.133
S = 1.05
4779 reflections
291 parameters
H-atom parameters constrained
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.22 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C12—H12⋯O1ⁱ	0.95	2.59	3.350 (3)	137
C22—H22⋯N3ⁱⁱ	0.95	2.61	3.487 (3)	154
C25—H25⋯O2ⁱⁱⁱ	0.95	2.56	3.484 (3)	164
Symmetry codes: (i) -x+1, -y+2, -z+1; (ii) -x+1, -y+1, -z+1; (iii) -x, -y+1, -z+2.

Data collection: CrysAlis PRO (Agilent, 2010); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811005770/xu5162sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811005770/xu5162Isup2.hkl

checkCIF report

Comment top

We have reported the antitumor activity of aryl-pyrazoles against CaCo-2 and HEP-2 cell lines (Abdel-Aziz et al., 2010). Among these is the title compound (Scheme I), whose biological properties will be reported elsewhere (Abdel-Aziz et al., 2011). The compound has methoxyphenylacryloyl, phenyl and tolyl substituents in the pyrazolyl ring. The methoxyphenylacryloyl substituent is twisted by 18.7 (1)° with respect to the pyrazolyl ring; the phenyl and tolyl substituents are aligned at 48.9 (1)° and 44.5 (1)° with respect to the five-membered ring (Fig. 1).

Related literature top

For background to the biological properties of aryl-substituted pyrazoles, see: Abdel-Aziz et al. (2010, 2011).

Experimental top

The synthesis will be reported elsewhere (Abdel-Aziz et al., 2011). 3-Acetyl-5-phenyl-1-p-tolyl-1H-pyrazole-4-carbonitrile (10 mmol) was reacted with 4-methoxybenzaldehyde (10 mmol) in presence of sodium ethoxide solution (prepared by dissolving 0.23 g sodium metal in 50 ml absolute ethanol). The compound was recrystallized from an ethanol-DMF (3:1) mixture.

Computing details top

Data collection: CrysAlis PRO (Agilent, 2010); cell refinement: CrysAlis PRO (Agilent, 2010); data reduction: CrysAlis PRO (Agilent, 2010); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of C₂₇H₂₁N₃O₂ at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.

3-[(E)-3-(4-Methoxyphenyl)prop-2-enoyl]-1-(4-methylphenyl)-5- phenyl-1H-pyrazole-4-carbonitrile top

Crystal data top

C₂₇H₂₁N₃O₂	Z = 2
M_r = 419.47	F(000) = 440
Triclinic, P1	D_x = 1.291 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.9995 (7) Å	Cell parameters from 2764 reflections
b = 11.0531 (8) Å	θ = 2.2–29.3°
c = 11.4381 (8) Å	µ = 0.08 mm⁻¹
α = 95.113 (6)°	T = 100 K
β = 111.582 (6)°	Prism, colorless
γ = 118.219 (7)°	0.20 × 0.15 × 0.05 mm
V = 1079.13 (18) Å³

Data collection top

Agilent SuperNova Dual diffractometer with Atlas detector	4779 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	3346 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.033
Detector resolution: 10.4041 pixels mm^-1	θ_max = 27.5°, θ_min = 2.2°
ω scan	h = −10→13
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	k = −13→14
T_min = 0.984, T_max = 0.996	l = −14→14
8250 measured reflections

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)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.133	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0431P)² + 0.3112P] where P = (F_o² + 2F_c²)/3
4779 reflections	(Δ/σ)_max = 0.001
291 parameters	Δρ_max = 0.21 e Å⁻³
0 restraints	Δρ_min = −0.22 e Å⁻³

Crystal data top

C₂₇H₂₁N₃O₂	γ = 118.219 (7)°
M_r = 419.47	V = 1079.13 (18) Å³
Triclinic, P1	Z = 2
a = 10.9995 (7) Å	Mo Kα radiation
b = 11.0531 (8) Å	µ = 0.08 mm⁻¹
c = 11.4381 (8) Å	T = 100 K
α = 95.113 (6)°	0.20 × 0.15 × 0.05 mm
β = 111.582 (6)°

Data collection top

Agilent SuperNova Dual diffractometer with Atlas detector	4779 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	3346 reflections with I > 2σ(I)
T_min = 0.984, T_max = 0.996	R_int = 0.033
8250 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.053	0 restraints
wR(F²) = 0.133	H-atom parameters constrained
S = 1.05	Δρ_max = 0.21 e Å⁻³
4779 reflections	Δρ_min = −0.22 e Å⁻³
291 parameters

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

	x	y	z	U_iso*/U_eq
O1	0.38684 (16)	0.57825 (15)	0.44798 (13)	0.0300 (3)
O2	0.12051 (18)	0.40793 (16)	1.05036 (14)	0.0367 (4)
N1	0.23698 (18)	0.80105 (17)	0.43686 (15)	0.0234 (4)
N2	0.24257 (18)	0.88927 (17)	0.36089 (15)	0.0224 (4)
N3	0.5147 (2)	0.73362 (19)	0.22677 (18)	0.0346 (4)
C1	0.3312 (2)	0.9656 (2)	0.19190 (18)	0.0240 (4)
C2	0.4740 (2)	1.0450 (2)	0.1918 (2)	0.0279 (4)
H2	0.5633	1.0516	0.2562	0.033*
C3	0.4859 (3)	1.1146 (2)	0.0974 (2)	0.0333 (5)
H3	0.5835	1.1689	0.0975	0.040*
C4	0.3566 (3)	1.1051 (2)	0.0037 (2)	0.0345 (5)
H4	0.3654	1.1535	−0.0602	0.041*
C5	0.2142 (3)	1.0253 (2)	0.0027 (2)	0.0351 (5)
H5	0.1252	1.0183	−0.0626	0.042*
C6	0.2004 (2)	0.9555 (2)	0.09631 (19)	0.0296 (5)
H6	0.1024	0.9011	0.0954	0.036*
C7	0.3174 (2)	0.8880 (2)	0.28932 (18)	0.0232 (4)
C8	0.3647 (2)	0.7940 (2)	0.32243 (18)	0.0231 (4)
C9	0.3105 (2)	0.7419 (2)	0.41342 (18)	0.0230 (4)
C10	0.4468 (2)	0.7579 (2)	0.26995 (19)	0.0253 (4)
C11	0.1709 (2)	0.9692 (2)	0.36361 (17)	0.0219 (4)
C12	0.2558 (2)	1.1174 (2)	0.39088 (18)	0.0242 (4)
H12	0.3621	1.1678	0.4095	0.029*
C13	0.1838 (2)	1.1919 (2)	0.39070 (18)	0.0258 (4)
H13	0.2418	1.2942	0.4103	0.031*
C14	0.0275 (2)	1.1190 (2)	0.36219 (18)	0.0237 (4)
C15	−0.0541 (2)	0.9696 (2)	0.33824 (18)	0.0254 (4)
H15	−0.1599	0.9188	0.3211	0.031*
C16	0.0174 (2)	0.8946 (2)	0.33918 (17)	0.0235 (4)
H16	−0.0386	0.7929	0.3232	0.028*
C17	−0.0532 (3)	1.1984 (2)	0.3558 (2)	0.0328 (5)
H17A	0.0250	1.3027	0.3984	0.049*
H17B	−0.1163	1.1647	0.4020	0.049*
H17C	−0.1209	1.1796	0.2627	0.049*
C18	0.3238 (2)	0.6344 (2)	0.47637 (18)	0.0238 (4)
C19	0.2638 (2)	0.6043 (2)	0.57209 (19)	0.0258 (4)
H19	0.1994	0.6368	0.5774	0.031*
C20	0.2979 (2)	0.5315 (2)	0.65250 (18)	0.0250 (4)
H20	0.3597	0.4983	0.6416	0.030*
C21	0.2506 (2)	0.4980 (2)	0.75476 (18)	0.0235 (4)
C22	0.3173 (2)	0.4435 (2)	0.84454 (19)	0.0259 (4)
H22	0.3919	0.4272	0.8368	0.031*
C23	0.2780 (2)	0.4123 (2)	0.94527 (19)	0.0274 (4)
H23	0.3254	0.3755	1.0058	0.033*
C24	0.1695 (2)	0.4353 (2)	0.95637 (19)	0.0285 (5)
C25	0.0980 (2)	0.4876 (2)	0.8662 (2)	0.0309 (5)
H25	0.0217	0.5016	0.8729	0.037*
C26	0.1392 (2)	0.5187 (2)	0.7676 (2)	0.0280 (4)
H26	0.0911	0.5550	0.7069	0.034*
C27	0.1885 (3)	0.3532 (3)	1.1453 (2)	0.0384 (5)
H27A	0.1401	0.3340	1.2040	0.058*
H27B	0.3008	0.4251	1.1981	0.058*
H27C	0.1710	0.2632	1.0988	0.058*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0359 (8)	0.0295 (8)	0.0345 (8)	0.0213 (7)	0.0202 (7)	0.0137 (7)
O2	0.0487 (10)	0.0439 (9)	0.0351 (8)	0.0303 (8)	0.0269 (8)	0.0228 (8)
N1	0.0264 (9)	0.0237 (8)	0.0233 (8)	0.0147 (8)	0.0126 (7)	0.0115 (7)
N2	0.0256 (9)	0.0241 (8)	0.0229 (8)	0.0154 (8)	0.0130 (7)	0.0111 (7)
N3	0.0394 (11)	0.0351 (10)	0.0423 (11)	0.0239 (9)	0.0255 (9)	0.0159 (9)
C1	0.0312 (11)	0.0218 (10)	0.0229 (10)	0.0155 (9)	0.0147 (9)	0.0080 (8)
C2	0.0316 (11)	0.0246 (10)	0.0310 (11)	0.0152 (9)	0.0178 (9)	0.0103 (9)
C3	0.0456 (13)	0.0264 (11)	0.0382 (12)	0.0187 (11)	0.0295 (11)	0.0137 (10)
C4	0.0575 (15)	0.0328 (12)	0.0295 (11)	0.0293 (12)	0.0278 (11)	0.0166 (10)
C5	0.0473 (14)	0.0437 (13)	0.0271 (11)	0.0306 (12)	0.0201 (10)	0.0170 (10)
C6	0.0328 (11)	0.0357 (12)	0.0274 (10)	0.0208 (10)	0.0170 (9)	0.0135 (10)
C7	0.0232 (10)	0.0252 (10)	0.0221 (9)	0.0132 (9)	0.0112 (8)	0.0080 (8)
C8	0.0227 (10)	0.0243 (10)	0.0236 (10)	0.0129 (9)	0.0116 (8)	0.0087 (8)
C9	0.0214 (10)	0.0238 (10)	0.0227 (10)	0.0118 (9)	0.0102 (8)	0.0070 (8)
C10	0.0283 (11)	0.0235 (10)	0.0289 (10)	0.0149 (9)	0.0159 (9)	0.0125 (9)
C11	0.0254 (10)	0.0271 (10)	0.0196 (9)	0.0179 (9)	0.0112 (8)	0.0099 (8)
C12	0.0213 (10)	0.0260 (10)	0.0255 (10)	0.0117 (9)	0.0122 (8)	0.0106 (9)
C13	0.0314 (11)	0.0242 (10)	0.0223 (10)	0.0155 (9)	0.0122 (9)	0.0089 (9)
C14	0.0302 (11)	0.0295 (11)	0.0186 (9)	0.0198 (9)	0.0127 (8)	0.0111 (8)
C15	0.0226 (10)	0.0335 (11)	0.0233 (10)	0.0160 (9)	0.0120 (8)	0.0123 (9)
C16	0.0252 (10)	0.0224 (10)	0.0218 (9)	0.0116 (9)	0.0113 (8)	0.0091 (8)
C17	0.0401 (13)	0.0365 (12)	0.0334 (11)	0.0266 (11)	0.0196 (10)	0.0147 (10)
C18	0.0215 (10)	0.0212 (10)	0.0251 (10)	0.0106 (9)	0.0093 (8)	0.0063 (8)
C19	0.0289 (11)	0.0245 (10)	0.0287 (10)	0.0156 (9)	0.0161 (9)	0.0108 (9)
C20	0.0250 (10)	0.0223 (10)	0.0267 (10)	0.0129 (9)	0.0114 (9)	0.0065 (9)
C21	0.0242 (10)	0.0197 (9)	0.0255 (10)	0.0120 (9)	0.0106 (8)	0.0072 (8)
C22	0.0254 (10)	0.0233 (10)	0.0291 (10)	0.0145 (9)	0.0111 (9)	0.0087 (9)
C23	0.0271 (11)	0.0253 (10)	0.0266 (10)	0.0145 (9)	0.0088 (9)	0.0098 (9)
C24	0.0341 (12)	0.0273 (11)	0.0258 (10)	0.0158 (10)	0.0164 (9)	0.0111 (9)
C25	0.0345 (12)	0.0343 (12)	0.0380 (12)	0.0236 (10)	0.0220 (10)	0.0181 (10)
C26	0.0334 (11)	0.0284 (11)	0.0308 (11)	0.0207 (10)	0.0164 (9)	0.0158 (9)
C27	0.0477 (14)	0.0395 (13)	0.0306 (11)	0.0243 (12)	0.0184 (11)	0.0185 (11)

Geometric parameters (Å, º) top

O1—C18	1.228 (2)	C13—C14	1.393 (3)
O2—C24	1.367 (2)	C13—H13	0.9500
O2—C27	1.432 (2)	C14—C15	1.394 (3)
N1—C9	1.335 (2)	C14—C17	1.505 (3)
N1—N2	1.358 (2)	C15—C16	1.386 (3)
N2—C7	1.361 (2)	C15—H15	0.9500
N2—C11	1.440 (2)	C16—H16	0.9500
N3—C10	1.146 (2)	C17—H17A	0.9800
C1—C2	1.391 (3)	C17—H17B	0.9800
C1—C6	1.396 (3)	C17—H17C	0.9800
C1—C7	1.474 (3)	C18—C19	1.461 (3)
C2—C3	1.390 (3)	C19—C20	1.340 (3)
C2—H2	0.9500	C19—H19	0.9500
C3—C4	1.378 (3)	C20—C21	1.456 (3)
C3—H3	0.9500	C20—H20	0.9500
C4—C5	1.382 (3)	C21—C22	1.390 (3)
C4—H4	0.9500	C21—C26	1.402 (3)
C5—C6	1.386 (3)	C22—C23	1.389 (3)
C5—H5	0.9500	C22—H22	0.9500
C6—H6	0.9500	C23—C24	1.378 (3)
C7—C8	1.389 (3)	C23—H23	0.9500
C8—C9	1.417 (3)	C24—C25	1.399 (3)
C8—C10	1.425 (3)	C25—C26	1.376 (3)
C9—C18	1.481 (3)	C25—H25	0.9500
C11—C12	1.379 (3)	C26—H26	0.9500
C11—C16	1.380 (3)	C27—H27A	0.9800
C12—C13	1.387 (3)	C27—H27B	0.9800
C12—H12	0.9500	C27—H27C	0.9800

C24—O2—C27	117.63 (16)	C16—C15—C14	120.69 (18)
C9—N1—N2	105.08 (14)	C16—C15—H15	119.7
N1—N2—C7	112.95 (14)	C14—C15—H15	119.7
N1—N2—C11	118.61 (14)	C11—C16—C15	119.32 (18)
C7—N2—C11	128.44 (15)	C11—C16—H16	120.3
C2—C1—C6	119.62 (18)	C15—C16—H16	120.3
C2—C1—C7	119.97 (17)	C14—C17—H17A	109.5
C6—C1—C7	120.36 (18)	C14—C17—H17B	109.5
C3—C2—C1	119.9 (2)	H17A—C17—H17B	109.5
C3—C2—H2	120.0	C14—C17—H17C	109.5
C1—C2—H2	120.0	H17A—C17—H17C	109.5
C4—C3—C2	120.2 (2)	H17B—C17—H17C	109.5
C4—C3—H3	119.9	O1—C18—C19	123.83 (18)
C2—C3—H3	119.9	O1—C18—C9	118.84 (17)
C5—C4—C3	120.02 (19)	C19—C18—C9	117.31 (16)
C5—C4—H4	120.0	C20—C19—C18	121.14 (18)
C3—C4—H4	120.0	C20—C19—H19	119.4
C4—C5—C6	120.5 (2)	C18—C19—H19	119.4
C4—C5—H5	119.8	C19—C20—C21	127.01 (18)
C6—C5—H5	119.8	C19—C20—H20	116.5
C5—C6—C1	119.7 (2)	C21—C20—H20	116.5
C5—C6—H6	120.1	C22—C21—C26	117.69 (18)
C1—C6—H6	120.1	C22—C21—C20	119.60 (17)
N2—C7—C8	105.58 (16)	C26—C21—C20	122.71 (17)
N2—C7—C1	124.52 (16)	C21—C22—C23	121.73 (18)
C8—C7—C1	129.79 (17)	C21—C22—H22	119.1
C7—C8—C9	105.63 (16)	C23—C22—H22	119.1
C7—C8—C10	125.37 (17)	C24—C23—C22	119.28 (18)
C9—C8—C10	128.98 (17)	C24—C23—H23	120.4
N1—C9—C8	110.75 (16)	C22—C23—H23	120.4
N1—C9—C18	120.93 (16)	O2—C24—C23	124.75 (18)
C8—C9—C18	128.29 (17)	O2—C24—C25	114.80 (18)
N3—C10—C8	177.4 (2)	C23—C24—C25	120.44 (18)
C12—C11—C16	121.29 (17)	C26—C25—C24	119.41 (19)
C12—C11—N2	119.98 (17)	C26—C25—H25	120.3
C16—C11—N2	118.73 (17)	C24—C25—H25	120.3
C11—C12—C13	119.05 (18)	C25—C26—C21	121.43 (18)
C11—C12—H12	120.5	C25—C26—H26	119.3
C13—C12—H12	120.5	C21—C26—H26	119.3
C12—C13—C14	120.95 (18)	O2—C27—H27A	109.5
C12—C13—H13	119.5	O2—C27—H27B	109.5
C14—C13—H13	119.5	H27A—C27—H27B	109.5
C13—C14—C15	118.65 (17)	O2—C27—H27C	109.5
C13—C14—C17	121.14 (18)	H27A—C27—H27C	109.5
C15—C14—C17	120.21 (18)	H27B—C27—H27C	109.5

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12···O1ⁱ	0.95	2.59	3.350 (3)	137
C22—H22···N3ⁱⁱ	0.95	2.61	3.487 (3)	154
C25—H25···O2ⁱⁱⁱ	0.95	2.56	3.484 (3)	164

Symmetry codes: (i) −x+1, −y+2, −z+1; (ii) −x+1, −y+1, −z+1; (iii) −x, −y+1, −z+2.

Experimental details

Crystal data
Chemical formula	C₂₇H₂₁N₃O₂
M_r	419.47
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	10.9995 (7), 11.0531 (8), 11.4381 (8)
α, β, γ (°)	95.113 (6), 111.582 (6), 118.219 (7)
V (Å³)	1079.13 (18)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.20 × 0.15 × 0.05

Data collection
Diffractometer	Agilent SuperNova Dual diffractometer with Atlas detector
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2010)
T_min, T_max	0.984, 0.996
No. of measured, independent and observed [I > 2σ(I)] reflections	8250, 4779, 3346
R_int	0.033
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.053, 0.133, 1.05
No. of reflections	4779
No. of parameters	291
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.21, −0.22

Computer programs: CrysAlis PRO (Agilent, 2010), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12···O1ⁱ	0.95	2.59	3.350 (3)	137
C22—H22···N3ⁱⁱ	0.95	2.61	3.487 (3)	154
C25—H25···O2ⁱⁱⁱ	0.95	2.56	3.484 (3)	164

Symmetry codes: (i) −x+1, −y+2, −z+1; (ii) −x+1, −y+1, −z+1; (iii) −x, −y+1, −z+2.

Acknowledgements

We thank King Saud University and the University of Malaya for supporting this study.

References

Abdel-Aziz, H. A., El-Zahabi, H. S. A. & Dawood, K. M. (2010). Eur. J. Med. Chem. 45, 2427–2432. Web of Science CAS PubMed Google Scholar
Abdel-Aziz, H. A., Nassar, E., Ibrahim, H. S. & Mansour, A. M. (2011). Bioorg. Med. Chem. Submitted. Google Scholar
Agilent (2010). CrysAlis PRO. Agilent Technologies, Yarnton, England. Google Scholar
Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 67| Part 3| March 2011| Page o694

doi:10.1107/S1600536811005770

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

3-[(E)-3-(4-Meth­­oxy­phen­yl)prop-2-eno­yl]-1-(4-methyl­phen­yl)-5-phenyl-1H-pyrazole-4-carbo­nitrile

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

3-[(E)-3-(4-Methoxyphenyl)prop-2-enoyl]-1-(4-methylphenyl)-5-phenyl-1H-pyrazole-4-carbonitrile