3-Acetyl-5-phenyl-1-p-tolyl-1H-pyrazole-4-carbonitrile.

In the title pyrazole derivative, C(19)H(15)N(3)O, the central pyrazole ring makes dihedral angles of 42.71 (9) and 61.34 (9)°, respectively, with the phenyl and p-tolyl rings. The dihedral angle between the phenyl and p-tolyl rings is 58.22 (9)°. The 3-acetyl-1H-pyrazole-4-carbonitrile unit is essentially planar, with an r.m.s. deviation of 0.0295 (1) Å for the ten non-H atoms.

Related literature

For bond-length data, see: Allen et al. (1987 ▶). For background to and the bioactivity of pyrazole derivatives, see: Abdel-Aziz et al. (2009 ▶, 2010 ▶); Abdel-Wahab et al. (2009 ▶); Dawood et al. (2003 ▶). For a related structure, see: Abdel-Aziz et al. (2012 ▶).

Experimental

Crystal data

C19H15N3O

M = 301.34

Monoclinic,

a = 10.2433 (2) Å

b = 10.6467 (2) Å

c = 15.7547 (3) Å

β = 109.684 (1)°

V = 1617.76 (5) Å3

Z = 4

Cu Kα radiation

μ = 0.63 mm−1

T = 296 K

0.57 × 0.28 × 0.22 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.718, T max = 0.876

10344 measured reflections

2720 independent reflections

2427 reflections with I > 2σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.118

S = 1.05

2720 reflections

213 parameters

H-atom parameters constrained

Δρmax = 0.20 e Å−3

Δρmin = −0.14 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/S1600536812011762/is5093sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812011762/is5093Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812011762/is5093Isup3.cml

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

C19H15N3O	F(000) = 632
Mr = 301.34	Dx = 1.237 Mg m−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: -P 2ybc	Cell parameters from 272 reflections
a = 10.2433 (2) Å	θ = 4.6–65.0°
b = 10.6467 (2) Å	µ = 0.63 mm−1
c = 15.7547 (3) Å	T = 296 K
β = 109.684 (1)°	Block, colorless
V = 1617.76 (5) Å3	0.57 × 0.28 × 0.22 mm
Z = 4

Bruker SMART APEXII CCD area-detector diffractometer	2720 independent reflections
Radiation source: sealed tube	2427 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.032
φ and ω scans	θmax = 65.0°, θmin = 4.6°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −12→11
Tmin = 0.718, Tmax = 0.876	k = −12→12
10344 measured reflections	l = −18→18

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)] = 0.042	H-atom parameters constrained
wR(F2) = 0.118	w = 1/[σ2(Fo2) + (0.050P)2 + 0.2871P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max = 0.001
2720 reflections	Δρmax = 0.20 e Å−3
213 parameters	Δρmin = −0.14 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: 0.0113 (9)

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
O1	−0.28761 (14)	0.55281 (14)	0.42141 (9)	0.0837 (4)
N1	0.05513 (13)	0.54275 (12)	0.68539 (8)	0.0536 (3)
N2	−0.05757 (13)	0.47588 (13)	0.63730 (8)	0.0585 (3)
N3	−0.07458 (17)	0.81153 (17)	0.43476 (10)	0.0795 (5)
C1	−0.11442 (15)	0.54122 (15)	0.56191 (10)	0.0544 (4)
C2	−0.03698 (14)	0.65058 (14)	0.56181 (9)	0.0513 (4)
C3	0.07256 (14)	0.64969 (14)	0.64318 (9)	0.0499 (4)
C4	−0.05890 (15)	0.74023 (16)	0.49130 (10)	0.0578 (4)
C5	0.18570 (15)	0.74010 (15)	0.67940 (9)	0.0521 (4)
C6	0.15724 (18)	0.86766 (16)	0.67039 (11)	0.0637 (4)
H6A	0.0669	0.8947	0.6412	0.076*
C7	0.2610 (2)	0.9544 (2)	0.70412 (14)	0.0833 (6)
H7A	0.2405	1.0398	0.6983	0.100*
C8	0.3956 (2)	0.9150 (2)	0.74673 (14)	0.0876 (6)
H8A	0.4659	0.9736	0.7699	0.105*
C9	0.42553 (18)	0.7887 (2)	0.75483 (13)	0.0781 (6)
H9A	0.5165	0.7624	0.7828	0.094*
C10	0.32237 (16)	0.70133 (18)	0.72207 (11)	0.0644 (4)
H10A	0.3435	0.6161	0.7283	0.077*
C11	0.13953 (15)	0.49602 (15)	0.77206 (9)	0.0530 (4)
C12	0.15432 (17)	0.56511 (16)	0.84811 (10)	0.0587 (4)
H12A	0.1096	0.6420	0.8442	0.070*
C13	0.23678 (17)	0.51883 (17)	0.93088 (10)	0.0625 (4)
H13A	0.2470	0.5654	0.9827	0.075*
C14	0.30436 (16)	0.40481 (17)	0.93820 (10)	0.0605 (4)
C15	0.2845 (2)	0.33649 (18)	0.86054 (12)	0.0723 (5)
H15A	0.3274	0.2587	0.8644	0.087*
C16	0.2024 (2)	0.38067 (17)	0.77706 (11)	0.0690 (5)
H16A	0.1900	0.3334	0.7253	0.083*
C17	−0.24206 (18)	0.49704 (17)	0.49213 (11)	0.0641 (4)
C18	−0.3103 (2)	0.3819 (2)	0.51218 (15)	0.0947 (7)
H18A	−0.3925	0.3639	0.4621	0.142*
H18B	−0.3346	0.3959	0.5652	0.142*
H18C	−0.2475	0.3122	0.5222	0.142*
C19	0.39693 (19)	0.3572 (2)	1.02859 (12)	0.0778 (5)
H19C	0.3602	0.2800	1.0425	0.117*
H19A	0.4011	0.4185	1.0741	0.117*
H19B	0.4884	0.3429	1.0266	0.117*

	U11	U22	U33	U12	U13	U23
O1	0.0771 (8)	0.0812 (9)	0.0701 (8)	0.0013 (7)	−0.0049 (6)	0.0061 (7)
N1	0.0510 (7)	0.0597 (7)	0.0486 (6)	0.0035 (5)	0.0147 (5)	0.0065 (5)
N2	0.0554 (7)	0.0637 (8)	0.0545 (7)	0.0002 (6)	0.0162 (6)	0.0032 (6)
N3	0.0781 (10)	0.0908 (11)	0.0680 (9)	0.0115 (8)	0.0223 (7)	0.0254 (9)
C1	0.0505 (8)	0.0616 (9)	0.0511 (8)	0.0074 (7)	0.0171 (6)	0.0015 (7)
C2	0.0465 (7)	0.0596 (8)	0.0488 (7)	0.0116 (6)	0.0171 (6)	0.0055 (6)
C3	0.0453 (7)	0.0566 (8)	0.0503 (7)	0.0093 (6)	0.0194 (6)	0.0063 (6)
C4	0.0488 (8)	0.0695 (10)	0.0540 (8)	0.0105 (7)	0.0161 (6)	0.0076 (8)
C5	0.0471 (7)	0.0632 (9)	0.0467 (7)	0.0054 (6)	0.0169 (6)	0.0085 (6)
C6	0.0585 (9)	0.0638 (10)	0.0639 (9)	0.0070 (7)	0.0144 (7)	0.0091 (7)
C7	0.0894 (14)	0.0662 (11)	0.0825 (12)	−0.0095 (10)	0.0134 (10)	0.0130 (9)
C8	0.0761 (12)	0.0946 (15)	0.0774 (12)	−0.0279 (11)	0.0067 (9)	0.0208 (11)
C9	0.0497 (9)	0.1040 (15)	0.0710 (10)	−0.0060 (9)	0.0075 (7)	0.0297 (10)
C10	0.0502 (8)	0.0743 (10)	0.0661 (9)	0.0068 (7)	0.0163 (7)	0.0184 (8)
C11	0.0500 (8)	0.0608 (9)	0.0486 (7)	0.0026 (6)	0.0172 (6)	0.0099 (6)
C12	0.0587 (9)	0.0603 (9)	0.0573 (8)	0.0057 (7)	0.0198 (7)	0.0049 (7)
C13	0.0638 (9)	0.0709 (10)	0.0504 (8)	−0.0040 (8)	0.0162 (7)	0.0027 (7)
C14	0.0503 (8)	0.0732 (10)	0.0569 (8)	−0.0028 (7)	0.0168 (7)	0.0164 (8)
C15	0.0816 (12)	0.0679 (10)	0.0680 (10)	0.0210 (9)	0.0259 (9)	0.0178 (8)
C16	0.0836 (12)	0.0681 (10)	0.0553 (9)	0.0156 (9)	0.0234 (8)	0.0060 (8)
C17	0.0581 (9)	0.0690 (10)	0.0606 (9)	0.0049 (8)	0.0139 (7)	−0.0033 (8)
C18	0.0866 (14)	0.1014 (16)	0.0848 (13)	−0.0296 (12)	0.0139 (11)	0.0028 (12)
C19	0.0634 (10)	0.0968 (14)	0.0650 (10)	0.0000 (9)	0.0110 (8)	0.0238 (10)

O1—C17	1.209 (2)	C9—H9A	0.9300
N1—N2	1.3507 (18)	C10—H10A	0.9300
N1—C3	1.3603 (19)	C11—C12	1.370 (2)
N1—C11	1.4367 (18)	C11—C16	1.377 (2)
N2—C1	1.330 (2)	C12—C13	1.384 (2)
N3—C4	1.140 (2)	C12—H12A	0.9300
C1—C2	1.409 (2)	C13—C14	1.383 (3)
C1—C17	1.473 (2)	C13—H13A	0.9300
C2—C3	1.390 (2)	C14—C15	1.378 (3)
C2—C4	1.424 (2)	C14—C19	1.508 (2)
C3—C5	1.466 (2)	C15—C16	1.383 (2)
C5—C6	1.386 (2)	C15—H15A	0.9300
C5—C10	1.396 (2)	C16—H16A	0.9300
C6—C7	1.373 (3)	C17—C18	1.496 (3)
C6—H6A	0.9300	C18—H18A	0.9600
C7—C8	1.380 (3)	C18—H18B	0.9600
C7—H7A	0.9300	C18—H18C	0.9600
C8—C9	1.375 (3)	C19—H19C	0.9600
C8—H8A	0.9300	C19—H19A	0.9600
C9—C10	1.372 (3)	C19—H19B	0.9600
N2—N1—C3	113.27 (12)	C12—C11—N1	119.94 (14)
N2—N1—C11	118.53 (12)	C16—C11—N1	118.91 (14)
C3—N1—C11	128.20 (13)	C11—C12—C13	119.05 (15)
C1—N2—N1	105.05 (13)	C11—C12—H12A	120.5
N2—C1—C2	110.85 (13)	C13—C12—H12A	120.5
N2—C1—C17	120.73 (15)	C14—C13—C12	121.38 (16)
C2—C1—C17	128.41 (14)	C14—C13—H13A	119.3
C3—C2—C1	105.85 (13)	C12—C13—H13A	119.3
C3—C2—C4	126.16 (14)	C15—C14—C13	117.98 (14)
C1—C2—C4	127.87 (13)	C15—C14—C19	121.26 (17)
N1—C3—C2	104.97 (13)	C13—C14—C19	120.77 (17)
N1—C3—C5	125.17 (13)	C14—C15—C16	121.69 (16)
C2—C3—C5	129.86 (13)	C14—C15—H15A	119.2
N3—C4—C2	178.98 (17)	C16—C15—H15A	119.2
C6—C5—C10	118.77 (16)	C11—C16—C15	118.74 (16)
C6—C5—C3	119.47 (13)	C11—C16—H16A	120.6
C10—C5—C3	121.76 (15)	C15—C16—H16A	120.6
C7—C6—C5	120.73 (16)	O1—C17—C1	120.06 (17)
C7—C6—H6A	119.6	O1—C17—C18	122.28 (17)
C5—C6—H6A	119.6	C1—C17—C18	117.66 (16)
C6—C7—C8	119.97 (19)	C17—C18—H18A	109.5
C6—C7—H7A	120.0	C17—C18—H18B	109.5
C8—C7—H7A	120.0	H18A—C18—H18B	109.5
C9—C8—C7	119.85 (19)	C17—C18—H18C	109.5
C9—C8—H8A	120.1	H18A—C18—H18C	109.5
C7—C8—H8A	120.1	H18B—C18—H18C	109.5
C10—C9—C8	120.58 (17)	C14—C19—H19C	109.5
C10—C9—H9A	119.7	C14—C19—H19A	109.5
C8—C9—H9A	119.7	H19C—C19—H19A	109.5
C9—C10—C5	120.08 (17)	C14—C19—H19B	109.5
C9—C10—H10A	120.0	H19C—C19—H19B	109.5
C5—C10—H10A	120.0	H19A—C19—H19B	109.5
C12—C11—C16	121.13 (14)
C3—N1—N2—C1	0.11 (16)	C6—C7—C8—C9	0.4 (3)
C11—N1—N2—C1	179.67 (13)	C7—C8—C9—C10	−1.0 (3)
N1—N2—C1—C2	0.18 (16)	C8—C9—C10—C5	0.5 (3)
N1—N2—C1—C17	−179.55 (13)	C6—C5—C10—C9	0.5 (2)
N2—C1—C2—C3	−0.39 (16)	C3—C5—C10—C9	179.78 (15)
C17—C1—C2—C3	179.31 (15)	N2—N1—C11—C12	−117.95 (16)
N2—C1—C2—C4	175.73 (14)	C3—N1—C11—C12	61.5 (2)
C17—C1—C2—C4	−4.6 (2)	N2—N1—C11—C16	60.91 (19)
N2—N1—C3—C2	−0.35 (16)	C3—N1—C11—C16	−119.60 (18)
C11—N1—C3—C2	−179.86 (13)	C16—C11—C12—C13	1.6 (2)
N2—N1—C3—C5	−179.96 (13)	N1—C11—C12—C13	−179.59 (14)
C11—N1—C3—C5	0.5 (2)	C11—C12—C13—C14	0.1 (3)
C1—C2—C3—N1	0.43 (15)	C12—C13—C14—C15	−1.6 (2)
C4—C2—C3—N1	−175.78 (13)	C12—C13—C14—C19	178.34 (16)
C1—C2—C3—C5	−179.98 (14)	C13—C14—C15—C16	1.5 (3)
C4—C2—C3—C5	3.8 (2)	C19—C14—C15—C16	−178.44 (18)
N1—C3—C5—C6	−138.02 (15)	C12—C11—C16—C15	−1.7 (3)
C2—C3—C5—C6	42.5 (2)	N1—C11—C16—C15	179.48 (16)
N1—C3—C5—C10	42.7 (2)	C14—C15—C16—C11	0.1 (3)
C2—C3—C5—C10	−136.79 (16)	N2—C1—C17—O1	−175.12 (16)
C10—C5—C6—C7	−1.1 (3)	C2—C1—C17—O1	5.2 (3)
C3—C5—C6—C7	179.61 (16)	N2—C1—C17—C18	4.4 (2)
C5—C6—C7—C8	0.7 (3)	C2—C1—C17—C18	−175.32 (18)