3-Acetyl-1-(3-methyl-phen-yl)-5-phenyl-1H-pyrazole-4-carbonitrile.

In the title compound, C(19)H(15)N(3)O, the central pyrazole ring makes dihedral angles of 35.52 (12) and 62.21 (11)° with the attached phenyl and methyl-substituted phenyl rings, respectively. The corresponding angle between the phenyl and methyl-substituted phenyl rings is 62.90 (11)°. In the crystal, mol-ecules are connected by weak C-H⋯O hydrogen bonds, forming supra-molecular chains propagating along the a-axis direction.

Related literature

For details and applications of pyrazole compounds, see: Kovbasyuk et al. (2004 ▶); Sachse et al. (2008 ▶); De Geest et al. (2007 ▶); Roy et al. (2008 ▶). For related structures, see: Fun et al. (2011 ▶). For further synthetic details, see: Nassar et al. (2011 ▶).

Experimental

Crystal data

C19H15N3O

M = 301.34

Monoclinic,

a = 11.8544 (8) Å

b = 7.6731 (6) Å

c = 17.4048 (15) Å

β = 96.202 (6)°

V = 1573.9 (2) Å3

Z = 4

Cu Kα radiation

μ = 0.65 mm−1

T = 296 K

0.55 × 0.21 × 0.16 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.717, T max = 0.902

8352 measured reflections

2776 independent reflections

1804 reflections with I > 2σ(I)

R int = 0.091

Refinement

R[F 2 > 2σ(F 2)] = 0.059

wR(F 2) = 0.227

S = 1.05

2776 reflections

209 parameters

H-atom parameters constrained

Δρmax = 0.27 e Å−3

Δρmin = −0.37 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/S160053681200181X/hb6607sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681200181X/hb6607Isup2.hkl

Supplementary material file. DOI: 10.1107/S160053681200181X/hb6607Isup3.cml

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

C19H15N3O	F(000) = 632
Mr = 301.34	Dx = 1.272 Mg m−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: -P 2ybc	Cell parameters from 1651 reflections
a = 11.8544 (8) Å	θ = 6.3–66.5°
b = 7.6731 (6) Å	µ = 0.65 mm−1
c = 17.4048 (15) Å	T = 296 K
β = 96.202 (6)°	Block, colourless
V = 1573.9 (2) Å3	0.55 × 0.21 × 0.16 mm
Z = 4

Bruker SMART APEXII CCD diffractometer	2776 independent reflections
Radiation source: fine-focus sealed tube	1804 reflections with I > 2σ(I)
graphite	Rint = 0.091
φ and ω scans	θmax = 67.4°, θmin = 3.8°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −11→14
Tmin = 0.717, Tmax = 0.902	k = −9→8
8352 measured reflections	l = −19→20

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.059	H-atom parameters constrained
wR(F2) = 0.227	w = 1/[σ2(Fo2) + (0.1264P)2 + 0.0573P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max < 0.001
2776 reflections	Δρmax = 0.27 e Å−3
209 parameters	Δρmin = −0.37 e Å−3
0 restraints	Extinction correction: SHELXTL (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0042 (13)

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 > 2σ(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
C1	0.18649 (19)	−0.0026 (3)	0.85181 (12)	0.0503 (7)
H1A	0.2331	−0.0955	0.8688	0.060*
C2	0.0758 (2)	0.0011 (3)	0.86879 (13)	0.0550 (7)
C3	0.0088 (2)	0.1432 (3)	0.84253 (14)	0.0586 (7)
H3A	−0.0662	0.1492	0.8534	0.070*
C4	0.0527 (2)	0.2746 (3)	0.80077 (14)	0.0590 (7)
H4A	0.0064	0.3677	0.7837	0.071*
C5	0.1629 (2)	0.2711 (3)	0.78384 (13)	0.0538 (6)
H5A	0.1924	0.3604	0.7559	0.065*
C6	0.22883 (19)	0.1295 (3)	0.80997 (12)	0.0461 (6)
N1	0.34545 (16)	0.1197 (2)	0.79402 (11)	0.0489 (6)
N2	0.42757 (17)	0.1217 (2)	0.85538 (11)	0.0523 (6)
C9	0.5249 (2)	0.1171 (3)	0.82443 (14)	0.0482 (6)
C10	0.5062 (2)	0.1118 (3)	0.74350 (13)	0.0496 (7)
C11	0.38934 (19)	0.1128 (2)	0.72492 (13)	0.0458 (6)
C12	0.32137 (19)	0.1023 (3)	0.64932 (13)	0.0480 (6)
C13	0.2211 (2)	0.0089 (3)	0.63772 (13)	0.0521 (6)
H13A	0.1937	−0.0474	0.6792	0.062*
C14	0.1610 (2)	−0.0016 (3)	0.56516 (14)	0.0615 (7)
H14A	0.0931	−0.0634	0.5583	0.074*
C15	0.2016 (2)	0.0791 (4)	0.50341 (16)	0.0684 (8)
H15A	0.1609	0.0724	0.4547	0.082*
C16	0.3012 (2)	0.1689 (3)	0.51313 (15)	0.0687 (8)
H16A	0.3289	0.2213	0.4708	0.082*
C17	0.3613 (2)	0.1829 (3)	0.58552 (13)	0.0588 (7)
H17A	0.4286	0.2462	0.5918	0.071*
C18	0.5895 (2)	0.1047 (3)	0.69062 (17)	0.0593 (7)
N4	0.6559 (2)	0.1033 (3)	0.64697 (16)	0.0835 (8)
C20	0.6343 (2)	0.1168 (3)	0.87444 (16)	0.0569 (7)
O1	0.72089 (16)	0.0876 (3)	0.84499 (12)	0.0754 (6)
C23	0.0279 (3)	−0.1453 (4)	0.91259 (19)	0.0857 (10)
H23A	0.0861	−0.2303	0.9263	0.129*
H23D	−0.0337	−0.1989	0.8808	0.129*
H23B	0.0008	−0.1002	0.9587	0.129*
C21	0.6332 (2)	0.1535 (4)	0.95825 (15)	0.0720 (8)
H21A	0.7093	0.1493	0.9834	0.108*
H21B	0.5877	0.0677	0.9806	0.108*
H21C	0.6018	0.2672	0.9648	0.108*

	U11	U22	U33	U12	U13	U23
C1	0.0445 (16)	0.0626 (13)	0.0437 (14)	0.0026 (10)	0.0046 (11)	0.0018 (9)
C2	0.0493 (16)	0.0690 (14)	0.0472 (13)	−0.0093 (11)	0.0078 (11)	−0.0001 (10)
C3	0.0421 (15)	0.0816 (16)	0.0528 (15)	0.0036 (11)	0.0086 (12)	−0.0018 (11)
C4	0.0484 (16)	0.0692 (14)	0.0592 (16)	0.0083 (12)	0.0045 (12)	0.0040 (11)
C5	0.0506 (15)	0.0614 (13)	0.0499 (14)	0.0022 (11)	0.0078 (11)	0.0052 (10)
C6	0.0397 (15)	0.0631 (12)	0.0358 (13)	0.0000 (9)	0.0048 (10)	−0.0027 (9)
N1	0.0401 (12)	0.0642 (11)	0.0426 (12)	0.0001 (8)	0.0054 (9)	−0.0009 (8)
N2	0.0423 (13)	0.0694 (12)	0.0443 (12)	−0.0013 (9)	0.0009 (10)	−0.0006 (8)
C9	0.0412 (15)	0.0551 (12)	0.0491 (15)	−0.0021 (9)	0.0083 (11)	−0.0004 (9)
C10	0.0449 (15)	0.0538 (12)	0.0515 (15)	0.0006 (9)	0.0112 (11)	−0.0009 (9)
C11	0.0479 (16)	0.0495 (11)	0.0413 (14)	−0.0013 (9)	0.0105 (11)	0.0015 (8)
C12	0.0470 (15)	0.0528 (12)	0.0452 (14)	0.0058 (9)	0.0100 (11)	−0.0015 (8)
C13	0.0524 (15)	0.0598 (13)	0.0446 (13)	0.0006 (11)	0.0080 (11)	−0.0033 (9)
C14	0.0573 (17)	0.0707 (15)	0.0553 (15)	0.0001 (12)	0.0007 (13)	−0.0077 (12)
C15	0.074 (2)	0.0811 (17)	0.0479 (16)	0.0099 (14)	−0.0039 (14)	−0.0015 (12)
C16	0.083 (2)	0.0761 (16)	0.0487 (16)	0.0035 (14)	0.0133 (14)	0.0132 (12)
C17	0.0654 (17)	0.0610 (14)	0.0510 (15)	−0.0043 (11)	0.0112 (12)	0.0052 (10)
C18	0.0510 (18)	0.0670 (15)	0.0610 (18)	−0.0022 (11)	0.0110 (14)	−0.0011 (11)
N4	0.0713 (18)	0.1056 (18)	0.0788 (19)	0.0031 (13)	0.0314 (15)	0.0018 (13)
C20	0.0425 (16)	0.0623 (14)	0.0655 (17)	−0.0066 (11)	0.0044 (13)	0.0035 (11)
O1	0.0429 (13)	0.0973 (14)	0.0857 (15)	−0.0028 (9)	0.0053 (11)	−0.0070 (10)
C23	0.077 (2)	0.096 (2)	0.088 (2)	−0.0160 (16)	0.0272 (18)	0.0198 (16)
C21	0.0598 (17)	0.0930 (19)	0.0603 (17)	−0.0084 (14)	−0.0071 (14)	−0.0044 (14)

C1—C6	1.375 (3)	C12—C13	1.384 (3)
C1—C2	1.376 (3)	C12—C17	1.398 (3)
C1—H1A	0.9300	C13—C14	1.384 (3)
C2—C3	1.396 (3)	C13—H13A	0.9300
C2—C23	1.503 (4)	C14—C15	1.372 (4)
C3—C4	1.377 (3)	C14—H14A	0.9300
C3—H3A	0.9300	C15—C16	1.362 (4)
C4—C5	1.370 (3)	C15—H15A	0.9300
C4—H4A	0.9300	C16—C17	1.383 (4)
C5—C6	1.386 (3)	C16—H16A	0.9300
C5—H5A	0.9300	C17—H17A	0.9300
C6—N1	1.441 (3)	C18—N4	1.151 (3)
N1—C11	1.362 (3)	C20—O1	1.217 (3)
N1—N2	1.365 (3)	C20—C21	1.487 (4)
N2—C9	1.325 (3)	C23—H23A	0.9600
C9—C10	1.403 (3)	C23—H23D	0.9600
C9—C20	1.482 (3)	C23—H23B	0.9600
C10—C11	1.388 (3)	C21—H21A	0.9600
C10—C18	1.422 (4)	C21—H21B	0.9600
C11—C12	1.469 (3)	C21—H21C	0.9600
C6—C1—C2	120.6 (2)	C17—C12—C11	119.2 (2)
C6—C1—H1A	119.7	C14—C13—C12	120.8 (2)
C2—C1—H1A	119.7	C14—C13—H13A	119.6
C1—C2—C3	117.9 (2)	C12—C13—H13A	119.6
C1—C2—C23	121.0 (2)	C15—C14—C13	120.0 (2)
C3—C2—C23	121.2 (2)	C15—C14—H14A	120.0
C4—C3—C2	120.7 (2)	C13—C14—H14A	120.0
C4—C3—H3A	119.6	C16—C15—C14	120.3 (2)
C2—C3—H3A	119.6	C16—C15—H15A	119.9
C5—C4—C3	121.5 (2)	C14—C15—H15A	119.9
C5—C4—H4A	119.3	C15—C16—C17	120.5 (2)
C3—C4—H4A	119.3	C15—C16—H16A	119.8
C4—C5—C6	117.5 (2)	C17—C16—H16A	119.8
C4—C5—H5A	121.3	C16—C17—C12	120.2 (2)
C6—C5—H5A	121.3	C16—C17—H17A	119.9
C1—C6—C5	121.8 (2)	C12—C17—H17A	119.9
C1—C6—N1	118.43 (19)	N4—C18—C10	178.1 (3)
C5—C6—N1	119.8 (2)	O1—C20—C9	118.5 (2)
C11—N1—N2	112.52 (19)	O1—C20—C21	123.0 (2)
C11—N1—C6	129.64 (18)	C9—C20—C21	118.4 (3)
N2—N1—C6	117.81 (19)	C2—C23—H23A	109.5
C9—N2—N1	105.08 (19)	C2—C23—H23D	109.5
N2—C9—C10	111.1 (2)	H23A—C23—H23D	109.5
N2—C9—C20	120.4 (2)	C2—C23—H23B	109.5
C10—C9—C20	128.5 (3)	H23A—C23—H23B	109.5
C11—C10—C9	106.2 (2)	H23D—C23—H23B	109.5
C11—C10—C18	126.5 (2)	C20—C21—H21A	109.5
C9—C10—C18	127.3 (2)	C20—C21—H21B	109.5
N1—C11—C10	105.15 (19)	H21A—C21—H21B	109.5
N1—C11—C12	124.6 (2)	C20—C21—H21C	109.5
C10—C11—C12	130.2 (2)	H21A—C21—H21C	109.5
C13—C12—C17	118.2 (2)	H21B—C21—H21C	109.5
C13—C12—C11	122.6 (2)
C6—C1—C2—C3	−0.3 (3)	C6—N1—C11—C10	177.65 (19)
C6—C1—C2—C23	178.3 (2)	N2—N1—C11—C12	177.50 (17)
C1—C2—C3—C4	0.2 (3)	C6—N1—C11—C12	−4.4 (3)
C23—C2—C3—C4	−178.4 (3)	C9—C10—C11—N1	0.4 (2)
C2—C3—C4—C5	−0.3 (4)	C18—C10—C11—N1	179.7 (2)
C3—C4—C5—C6	0.4 (4)	C9—C10—C11—C12	−177.45 (19)
C2—C1—C6—C5	0.4 (3)	C18—C10—C11—C12	1.9 (3)
C2—C1—C6—N1	179.76 (18)	N1—C11—C12—C13	−36.0 (3)
C4—C5—C6—C1	−0.5 (3)	C10—C11—C12—C13	141.5 (2)
C4—C5—C6—N1	−179.78 (19)	N1—C11—C12—C17	146.9 (2)
C1—C6—N1—C11	119.3 (2)	C10—C11—C12—C17	−35.6 (3)
C5—C6—N1—C11	−61.3 (3)	C17—C12—C13—C14	−1.1 (3)
C1—C6—N1—N2	−62.6 (2)	C11—C12—C13—C14	−178.3 (2)
C5—C6—N1—N2	116.7 (2)	C12—C13—C14—C15	0.9 (4)
C11—N1—N2—C9	0.4 (2)	C13—C14—C15—C16	0.3 (4)
C6—N1—N2—C9	−177.99 (17)	C14—C15—C16—C17	−1.3 (4)
N1—N2—C9—C10	−0.1 (2)	C15—C16—C17—C12	1.1 (4)
N1—N2—C9—C20	−179.71 (19)	C13—C12—C17—C16	0.2 (3)
N2—C9—C10—C11	−0.2 (2)	C11—C12—C17—C16	177.4 (2)
C20—C9—C10—C11	179.4 (2)	N2—C9—C20—O1	169.6 (2)
N2—C9—C10—C18	−179.5 (2)	C10—C9—C20—O1	−9.9 (3)
C20—C9—C10—C18	0.0 (4)	N2—C9—C20—C21	−10.8 (3)
N2—N1—C11—C10	−0.5 (2)	C10—C9—C20—C21	169.7 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3A···O1i	0.93	2.56	3.444 (3)	160

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3A⋯O1i	0.93	2.56	3.444 (3)	160

Symmetry code: (i) .