Literature DB >> 21522439

3-[(E)-3-(4-Meth-oxy-phen-yl)prop-2-eno-yl]-1-(4-methyl-phen-yl)-5-phenyl-1H-pyrazole-4-carbonitrile.

Hatem A Abdel-Aziz, Ahmed Bari, Seik Weng Ng.

Abstract

In the title compound, C(27)H(21)N(3)O(2), the non-H atoms of the meth-oxy-phenyl-acryloyl 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 inter-molecular C-H⋯O and C-H⋯N hydrogen bonding is present in the crystal structure.

Entities: CellLine Chemical Disease Gene

Year: 2011 PMID： 21522439 PMCID： PMC3052011 DOI： 10.1107/S1600536811005770

Source DB: PubMed Journal: Acta Crystallogr Sect E Struct Rep Online ISSN： 1600-5368

Related literature

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

Experimental

Crystal data

C27H21N3O2 M = 419.47 Triclinic, 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[F 2 > 2σ(F 2)] = 0.053 wR(F 2) = 0.133 S = 1.05 4779 reflections 291 parameters H-atom parameters constrained Δρmax = 0.21 e Å−3 Δρmin = −0.22 e Å−3 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 ▶). Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811005770/xu5162sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536811005770/xu5162Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report

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

Agilent SuperNova Dual diffractometer with Atlas detector	4779 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	3346 reflections with I > 2σ(I)
Mirror	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 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

	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*

	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)

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

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

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) ; (ii) ; (iii) .

2 in total

1. A short history of SHELX.

Authors: George M Sheldrick
Journal: Acta Crystallogr A Date: 2007-12-21 Impact factor: 2.290

2. Microwave-assisted synthesis and in-vitro anti-tumor activity of 1,3,4-triaryl-5-N-arylpyrazole-carboxamides.

Authors: Hatem A Abdel-Aziz; Heba S A El-Zahabi; Kamal M Dawood
Journal: Eur J Med Chem Date: 2010-02-16 Impact factor: 6.514

2 in total

1 in total

1. Synthesis of Diarylpyrazoles Containing a Phenylsulphone or Carbonitrile Moiety and their Chalcones as Possible Anti-Inflammatory Agents.

Authors: Ekhlass Nassar; Hatem A Abdel-Aziz; Hany S Ibrahim; Ahmed M Mansour
Journal: Sci Pharm Date: 2011-07-03

1 in total