3-Acetyl-1,5-diphenyl-1H-pyrazole-4-carbonitrile.

The title compound, C(18)H(13)N(3)O, has a butterfly-like structure, in which the pyrazole ring forms dihedral angles of 59.31 (8) and 57.24 (8)° with the two phenyl rings. The dihedral angle between the two phenyl rings is 64.03 (8)°. The pyrazole ring and the C-C=O plane of the acetyl group are twisted slightly, making a dihedral angle of 7.95 (18)°. In the crystal, mol-ecules are linked through weak C-H⋯N and C-H⋯O inter-actions into a helical chain along the a-axis direction.

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 ▶); Bharate et al. (2008 ▶); Dawood et al. (2003 ▶); Fu et al. (2010 ▶); Thumar & Patel (2011 ▶). For a related structure, see: Abdel-Aziz et al. (2011 ▶).

Experimental

Crystal data

C18H13N3O

M = 287.31

Orthorhombic,

a = 6.8322 (2) Å

b = 16.8974 (5) Å

c = 25.7968 (6) Å

V = 2978.15 (14) Å3

Z = 8

Cu Kα radiation

μ = 0.66 mm−1

T = 296 K

0.56 × 0.35 × 0.23 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.708, T max = 0.863

10678 measured reflections

2782 independent reflections

2338 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.116

S = 1.08

2782 reflections

201 parameters

H-atom parameters constrained

Δρmax = 0.18 e Å−3

Δρmin = −0.17 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/S1600536812010938/is5091sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812010938/is5091Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812010938/is5091Isup3.cml

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

C18H13N3O	F(000) = 1200
Mr = 287.31	Dx = 1.282 Mg m−3
Orthorhombic, Pbca	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 2782 reflections
a = 6.8322 (2) Å	θ = 3.4–69.9°
b = 16.8974 (5) Å	µ = 0.66 mm−1
c = 25.7968 (6) Å	T = 296 K
V = 2978.15 (14) Å3	Block, colorless
Z = 8	0.56 × 0.35 × 0.23 mm

Bruker SMART APEXII CCD area-detector diffractometer	2782 independent reflections
Radiation source: sealed tube	2338 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.026
φ and ω scans	θmax = 69.9°, θmin = 3.4°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −6→8
Tmin = 0.708, Tmax = 0.863	k = −20→20
10678 measured reflections	l = −31→23

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)] = 0.039	H-atom parameters constrained
wR(F2) = 0.116	w = 1/[σ2(Fo2) + (0.0586P)2 + 0.4109P] where P = (Fo2 + 2Fc2)/3
S = 1.08	(Δ/σ)max = 0.001
2782 reflections	Δρmax = 0.18 e Å−3
201 parameters	Δρmin = −0.17 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: 0.0012 (2)

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
N1	0.04907 (16)	0.77988 (6)	0.34667 (4)	0.0461 (3)
N2	0.03430 (17)	0.83315 (7)	0.30758 (4)	0.0501 (3)
N3	0.1596 (2)	0.59304 (10)	0.21580 (6)	0.0737 (4)
O1	0.05198 (19)	0.78631 (8)	0.17444 (4)	0.0747 (4)
C1	0.06117 (18)	0.79131 (8)	0.26452 (5)	0.0480 (3)
C2	0.09573 (19)	0.71052 (8)	0.27627 (5)	0.0463 (3)
C3	0.08526 (18)	0.70532 (8)	0.32961 (5)	0.0441 (3)
C4	0.1299 (2)	0.64619 (10)	0.24210 (5)	0.0536 (4)
C5	0.0947 (2)	0.63535 (8)	0.36354 (5)	0.0458 (3)
C6	0.2582 (2)	0.58729 (10)	0.36412 (6)	0.0628 (4)
H6A	0.3661	0.5995	0.3436	0.075*
C7	0.2603 (3)	0.52048 (10)	0.39553 (8)	0.0783 (5)
H7A	0.3702	0.4880	0.3961	0.094*
C8	0.1016 (4)	0.50213 (10)	0.42561 (7)	0.0785 (6)
H8A	0.1043	0.4575	0.4467	0.094*
C9	−0.0597 (3)	0.54911 (10)	0.42477 (7)	0.0741 (5)
H9A	−0.1675	0.5363	0.4451	0.089*
C10	−0.0647 (2)	0.61553 (9)	0.39400 (6)	0.0580 (4)
H10A	−0.1758	0.6473	0.3937	0.070*
C11	0.0388 (2)	0.80605 (8)	0.39950 (5)	0.0466 (3)
C12	0.1957 (2)	0.79135 (9)	0.43180 (6)	0.0566 (4)
H12A	0.3064	0.7656	0.4194	0.068*
C13	0.1858 (3)	0.81549 (10)	0.48280 (6)	0.0650 (4)
H13A	0.2901	0.8055	0.5050	0.078*
C14	0.0225 (3)	0.85426 (9)	0.50097 (6)	0.0658 (4)
H14A	0.0164	0.8703	0.5354	0.079*
C15	−0.1319 (3)	0.86926 (10)	0.46807 (6)	0.0662 (4)
H15A	−0.2414	0.8961	0.4803	0.079*
C16	−0.1254 (2)	0.84480 (9)	0.41697 (6)	0.0576 (4)
H16A	−0.2302	0.8544	0.3948	0.069*
C17	0.0492 (2)	0.82851 (10)	0.21251 (5)	0.0568 (4)
C18	0.0336 (3)	0.91591 (11)	0.20952 (7)	0.0755 (5)
H18A	−0.0431	0.9303	0.1798	0.113*
H18C	0.1621	0.9384	0.2065	0.113*
H18D	−0.0284	0.9356	0.2403	0.113*

	U11	U22	U33	U12	U13	U23
N1	0.0550 (6)	0.0450 (6)	0.0383 (5)	−0.0011 (5)	−0.0011 (4)	0.0056 (4)
N2	0.0541 (6)	0.0525 (6)	0.0438 (6)	−0.0019 (5)	−0.0021 (5)	0.0112 (5)
N3	0.0732 (9)	0.0852 (10)	0.0626 (8)	0.0025 (8)	0.0026 (7)	−0.0182 (8)
O1	0.0859 (8)	0.0965 (9)	0.0417 (6)	−0.0136 (7)	−0.0014 (5)	0.0109 (6)
C1	0.0429 (6)	0.0603 (8)	0.0407 (7)	−0.0073 (6)	−0.0012 (5)	0.0096 (6)
C2	0.0429 (6)	0.0566 (8)	0.0395 (6)	−0.0071 (6)	0.0003 (5)	0.0014 (6)
C3	0.0446 (6)	0.0474 (7)	0.0404 (6)	−0.0036 (5)	0.0002 (5)	0.0014 (5)
C4	0.0479 (7)	0.0701 (9)	0.0429 (7)	−0.0050 (7)	0.0009 (6)	−0.0026 (7)
C5	0.0579 (7)	0.0430 (7)	0.0363 (6)	−0.0014 (6)	−0.0021 (5)	−0.0020 (5)
C6	0.0642 (9)	0.0621 (9)	0.0622 (9)	0.0079 (7)	−0.0024 (7)	−0.0025 (7)
C7	0.0960 (13)	0.0558 (9)	0.0832 (12)	0.0250 (9)	−0.0237 (11)	−0.0051 (9)
C8	0.1315 (17)	0.0486 (9)	0.0554 (9)	0.0027 (10)	−0.0064 (10)	0.0067 (7)
C9	0.1125 (14)	0.0530 (9)	0.0568 (9)	−0.0034 (9)	0.0177 (9)	0.0085 (7)
C10	0.0738 (9)	0.0493 (8)	0.0508 (8)	0.0007 (7)	0.0113 (7)	0.0040 (6)
C11	0.0603 (7)	0.0395 (6)	0.0400 (6)	−0.0025 (6)	−0.0011 (6)	0.0034 (5)
C12	0.0651 (9)	0.0520 (8)	0.0526 (8)	0.0055 (7)	−0.0077 (6)	−0.0043 (6)
C13	0.0863 (11)	0.0575 (9)	0.0511 (8)	0.0016 (8)	−0.0186 (8)	−0.0037 (7)
C14	0.0962 (12)	0.0568 (9)	0.0445 (8)	−0.0048 (8)	−0.0002 (8)	−0.0051 (7)
C15	0.0801 (10)	0.0616 (9)	0.0571 (9)	0.0084 (8)	0.0100 (8)	−0.0040 (7)
C16	0.0650 (9)	0.0580 (8)	0.0499 (8)	0.0069 (7)	−0.0005 (6)	0.0038 (7)
C17	0.0460 (7)	0.0792 (10)	0.0451 (8)	−0.0084 (7)	−0.0012 (6)	0.0152 (7)
C18	0.0816 (11)	0.0821 (12)	0.0627 (10)	0.0030 (9)	0.0005 (8)	0.0291 (9)

N1—N2	1.3555 (15)	C9—C10	1.375 (2)
N1—C3	1.3572 (17)	C9—H9A	0.9300
N1—C11	1.4346 (17)	C10—H10A	0.9300
N2—C1	1.3294 (18)	C11—C16	1.375 (2)
N3—C4	1.144 (2)	C11—C12	1.380 (2)
O1—C17	1.214 (2)	C12—C13	1.379 (2)
C1—C2	1.418 (2)	C12—H12A	0.9300
C1—C17	1.4840 (18)	C13—C14	1.376 (3)
C2—C3	1.3807 (18)	C13—H13A	0.9300
C2—C4	1.419 (2)	C14—C15	1.378 (2)
C3—C5	1.4724 (18)	C14—H14A	0.9300
C5—C6	1.381 (2)	C15—C16	1.382 (2)
C5—C10	1.384 (2)	C15—H15A	0.9300
C6—C7	1.390 (2)	C16—H16A	0.9300
C6—H6A	0.9300	C17—C18	1.483 (2)
C7—C8	1.369 (3)	C18—H18A	0.9600
C7—H7A	0.9300	C18—H18C	0.9600
C8—C9	1.359 (3)	C18—H18D	0.9600
C8—H8A	0.9300
N2—N1—C3	112.88 (11)	C9—C10—H10A	119.8
N2—N1—C11	119.90 (10)	C5—C10—H10A	119.8
C3—N1—C11	127.08 (11)	C16—C11—C12	121.44 (13)
C1—N2—N1	104.96 (11)	C16—C11—N1	119.87 (12)
N2—C1—C2	110.88 (11)	C12—C11—N1	118.69 (12)
N2—C1—C17	121.50 (13)	C13—C12—C11	118.99 (15)
C2—C1—C17	127.60 (13)	C13—C12—H12A	120.5
C3—C2—C1	105.40 (12)	C11—C12—H12A	120.5
C3—C2—C4	125.39 (13)	C14—C13—C12	120.36 (15)
C1—C2—C4	129.20 (13)	C14—C13—H13A	119.8
N1—C3—C2	105.88 (11)	C12—C13—H13A	119.8
N1—C3—C5	124.11 (11)	C13—C14—C15	119.91 (14)
C2—C3—C5	129.87 (12)	C13—C14—H14A	120.0
N3—C4—C2	177.90 (16)	C15—C14—H14A	120.0
C6—C5—C10	119.21 (14)	C14—C15—C16	120.54 (15)
C6—C5—C3	120.93 (13)	C14—C15—H15A	119.7
C10—C5—C3	119.83 (12)	C16—C15—H15A	119.7
C5—C6—C7	119.48 (16)	C11—C16—C15	118.75 (15)
C5—C6—H6A	120.3	C11—C16—H16A	120.6
C7—C6—H6A	120.3	C15—C16—H16A	120.6
C8—C7—C6	120.43 (17)	O1—C17—C18	122.97 (14)
C8—C7—H7A	119.8	O1—C17—C1	118.81 (15)
C6—C7—H7A	119.8	C18—C17—C1	118.22 (14)
C9—C8—C7	120.07 (16)	C17—C18—H18A	109.5
C9—C8—H8A	120.0	C17—C18—H18C	109.5
C7—C8—H8A	120.0	H18A—C18—H18C	109.5
C8—C9—C10	120.41 (18)	C17—C18—H18D	109.5
C8—C9—H9A	119.8	H18A—C18—H18D	109.5
C10—C9—H9A	119.8	H18C—C18—H18D	109.5
C9—C10—C5	120.39 (16)
C3—N1—N2—C1	0.20 (14)	C5—C6—C7—C8	0.2 (3)
C11—N1—N2—C1	176.31 (11)	C6—C7—C8—C9	0.3 (3)
N1—N2—C1—C2	−0.67 (14)	C7—C8—C9—C10	−0.4 (3)
N1—N2—C1—C17	177.93 (11)	C8—C9—C10—C5	0.0 (3)
N2—C1—C2—C3	0.89 (15)	C6—C5—C10—C9	0.5 (2)
C17—C1—C2—C3	−177.61 (12)	C3—C5—C10—C9	178.21 (14)
N2—C1—C2—C4	179.54 (13)	N2—N1—C11—C16	59.51 (17)
C17—C1—C2—C4	1.0 (2)	C3—N1—C11—C16	−124.99 (15)
N2—N1—C3—C2	0.34 (14)	N2—N1—C11—C12	−120.59 (14)
C11—N1—C3—C2	−175.42 (12)	C3—N1—C11—C12	54.91 (19)
N2—N1—C3—C5	−175.66 (11)	C16—C11—C12—C13	0.7 (2)
C11—N1—C3—C5	8.6 (2)	N1—C11—C12—C13	−179.21 (13)
C1—C2—C3—N1	−0.71 (14)	C11—C12—C13—C14	−0.6 (2)
C4—C2—C3—N1	−179.43 (12)	C12—C13—C14—C15	−0.1 (3)
C1—C2—C3—C5	174.97 (13)	C13—C14—C15—C16	0.8 (3)
C4—C2—C3—C5	−3.7 (2)	C12—C11—C16—C15	0.0 (2)
N1—C3—C5—C6	−124.42 (15)	N1—C11—C16—C15	179.86 (14)
C2—C3—C5—C6	60.6 (2)	C14—C15—C16—C11	−0.7 (3)
N1—C3—C5—C10	57.90 (18)	N2—C1—C17—O1	−171.47 (13)
C2—C3—C5—C10	−117.09 (16)	C2—C1—C17—O1	6.9 (2)
C10—C5—C6—C7	−0.5 (2)	N2—C1—C17—C18	8.3 (2)
C3—C5—C6—C7	−178.24 (14)	C2—C1—C17—C18	−173.32 (14)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6A···N3i	0.93	2.53	3.432 (2)	165
C16—H16A···O1ii	0.93	2.59	3.3758 (19)	142

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6A⋯N3i	0.93	2.53	3.432 (2)	165
C16—H16A⋯O1ii	0.93	2.59	3.3758 (19)	142

Symmetry codes: (i) ; (ii) .