(2E)-3-(1,3-Diphenyl-1H-pyrazol-4-yl)-1-phenyl-prop-2-en-1-one.

In the title compound, C(24)H(18)N(2)O, the pyrazole ring is essentially planar [maximum deviation = 0.004 (1) Å] and makes dihedral angles of 18.07 (4), 48.60 (4) and 9.13 (5)° with the phenyl rings. In the crystal, adjacent mol-ecules are connected via inter-molecular C-H⋯O hydrogen bonds, forming dimers. Furthermore, the crystal structure is stabilized by weak C-H⋯π and π-π inter-actions, with centroid-centroid distances of 3.6808 (5) Å.

Related literature

For applications of pyrazoles, see: Patel et al. (2004 ▶); Isloor et al. (2009 ▶); Vijesh et al. (2010 ▶); Sharma et al. (2010 ▶); Rostom et al. (2003 ▶); Ghorab et al. (2010 ▶); Amnekar & Bhusari (2010 ▶). For the synthetic procedure, see: Sharma et al. (2010 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C24H18N2O

M = 350.40

Triclinic,

a = 8.1027 (2) Å

b = 9.3157 (2) Å

c = 12.9634 (3) Å

α = 73.630 (1)°

β = 74.713 (1)°

γ = 74.820 (1)°

V = 886.83 (4) Å3

Z = 2

Mo Kα radiation

μ = 0.08 mm−1

T = 100 K

0.66 × 0.23 × 0.16 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.949, T max = 0.988

27273 measured reflections

7371 independent reflections

6190 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.131

S = 1.04

7371 reflections

244 parameters

H-atom parameters constrained

Δρmax = 0.50 e Å−3

Δρmin = −0.30 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/S1600536811023282/rz2615sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811023282/rz2615Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811023282/rz2615Isup3.cml

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

C24H18N2O	Z = 2
Mr = 350.40	F(000) = 368
Triclinic, P1	Dx = 1.312 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.1027 (2) Å	Cell parameters from 9964 reflections
b = 9.3157 (2) Å	θ = 2.3–34.3°
c = 12.9634 (3) Å	µ = 0.08 mm−1
α = 73.630 (1)°	T = 100 K
β = 74.713 (1)°	Block, colourless
γ = 74.820 (1)°	0.66 × 0.23 × 0.16 mm
V = 886.83 (4) Å3

Bruker SMART APEXII CCD area-detector diffractometer	7371 independent reflections
Radiation source: fine-focus sealed tube	6190 reflections with I > 2σ(I)
graphite	Rint = 0.024
φ and ω scans	θmax = 34.4°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −12→12
Tmin = 0.949, Tmax = 0.988	k = −14→14
27273 measured reflections	l = −20→19

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.131	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0751P)2 + 0.1576P] where P = (Fo2 + 2Fc2)/3
7371 reflections	(Δ/σ)max = 0.001
244 parameters	Δρmax = 0.50 e Å−3
0 restraints	Δρmin = −0.30 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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	0.62674 (8)	0.29923 (7)	0.35790 (5)	0.02264 (13)
N1	−0.05079 (9)	0.77669 (8)	0.50245 (5)	0.01568 (12)
N2	−0.12324 (9)	0.77040 (8)	0.42026 (5)	0.01623 (12)
C1	0.70994 (10)	0.10968 (9)	0.21010 (6)	0.01851 (14)
H1A	0.7701	0.0780	0.2690	0.022*
C2	0.75836 (11)	0.02845 (9)	0.12812 (7)	0.02144 (15)
H2A	0.8514	−0.0584	0.1312	0.026*
C3	0.67086 (12)	0.07414 (10)	0.04162 (7)	0.02281 (16)
H3A	0.7029	0.0177	−0.0137	0.027*
C4	0.53661 (12)	0.20236 (11)	0.03622 (7)	0.02424 (16)
H4A	0.4781	0.2345	−0.0235	0.029*
C5	0.48746 (11)	0.28408 (10)	0.11820 (7)	0.02067 (15)
H5A	0.3953	0.3716	0.1142	0.025*
C6	0.57315 (10)	0.23783 (8)	0.20632 (6)	0.01585 (13)
C7	0.52409 (10)	0.31976 (8)	0.29762 (6)	0.01587 (13)
C8	0.35228 (10)	0.42396 (9)	0.31234 (6)	0.01641 (13)
H8A	0.2708	0.4290	0.2698	0.020*
C9	0.31000 (10)	0.51223 (9)	0.38577 (6)	0.01634 (13)
H9A	0.3974	0.5030	0.4251	0.020*
C10	0.14917 (10)	0.61871 (8)	0.41212 (6)	0.01493 (12)
C11	−0.00317 (10)	0.67559 (8)	0.36519 (6)	0.01476 (12)
C12	0.11129 (10)	0.68879 (8)	0.49939 (6)	0.01588 (13)
H12A	0.1858	0.6770	0.5481	0.019*
C13	−0.04028 (10)	0.65220 (8)	0.26639 (6)	0.01507 (12)
C14	0.08119 (10)	0.67017 (9)	0.16654 (6)	0.01730 (13)
H14A	0.1920	0.6890	0.1640	0.021*
C15	0.04095 (11)	0.66063 (9)	0.07101 (6)	0.02009 (14)
H15A	0.1240	0.6731	0.0037	0.024*
C16	−0.12143 (12)	0.63272 (10)	0.07439 (7)	0.02177 (15)
H16A	−0.1498	0.6271	0.0092	0.026*
C17	−0.24183 (11)	0.61317 (9)	0.17338 (7)	0.02090 (15)
H17A	−0.3518	0.5928	0.1758	0.025*
C18	−0.20240 (10)	0.62324 (9)	0.26905 (6)	0.01804 (14)
H18A	−0.2858	0.6104	0.3362	0.022*
C19	−0.14395 (10)	0.87250 (9)	0.57610 (6)	0.01661 (13)
C20	−0.29759 (11)	0.97422 (9)	0.55476 (7)	0.01987 (14)
H20A	−0.3394	0.9800	0.4915	0.024*
C21	−0.38932 (12)	1.06744 (10)	0.62720 (7)	0.02283 (16)
H21A	−0.4949	1.1362	0.6136	0.027*
C22	−0.32750 (12)	1.06055 (10)	0.71912 (8)	0.02431 (17)
H22A	−0.3906	1.1241	0.7684	0.029*
C23	−0.17285 (12)	0.96010 (12)	0.73845 (8)	0.02685 (18)
H23A	−0.1295	0.9565	0.8007	0.032*
C24	−0.08031 (11)	0.86448 (11)	0.66779 (7)	0.02333 (16)
H24A	0.0245	0.7949	0.6820	0.028*

	U11	U22	U33	U12	U13	U23
O1	0.0202 (3)	0.0266 (3)	0.0242 (3)	0.0010 (2)	−0.0109 (2)	−0.0099 (2)
N1	0.0156 (3)	0.0183 (3)	0.0144 (3)	−0.0022 (2)	−0.0034 (2)	−0.0065 (2)
N2	0.0160 (3)	0.0189 (3)	0.0151 (3)	−0.0022 (2)	−0.0045 (2)	−0.0059 (2)
C1	0.0177 (3)	0.0176 (3)	0.0184 (3)	0.0004 (2)	−0.0047 (2)	−0.0039 (2)
C2	0.0221 (4)	0.0182 (3)	0.0214 (3)	0.0009 (3)	−0.0033 (3)	−0.0062 (3)
C3	0.0245 (4)	0.0245 (4)	0.0203 (3)	−0.0032 (3)	−0.0022 (3)	−0.0103 (3)
C4	0.0233 (4)	0.0310 (4)	0.0191 (3)	−0.0001 (3)	−0.0069 (3)	−0.0093 (3)
C5	0.0184 (3)	0.0238 (4)	0.0193 (3)	0.0014 (3)	−0.0069 (3)	−0.0066 (3)
C6	0.0149 (3)	0.0161 (3)	0.0163 (3)	−0.0012 (2)	−0.0042 (2)	−0.0042 (2)
C7	0.0152 (3)	0.0157 (3)	0.0169 (3)	−0.0017 (2)	−0.0048 (2)	−0.0040 (2)
C8	0.0144 (3)	0.0171 (3)	0.0183 (3)	−0.0010 (2)	−0.0046 (2)	−0.0056 (2)
C9	0.0148 (3)	0.0180 (3)	0.0166 (3)	−0.0020 (2)	−0.0041 (2)	−0.0050 (2)
C10	0.0144 (3)	0.0158 (3)	0.0152 (3)	−0.0024 (2)	−0.0035 (2)	−0.0046 (2)
C11	0.0151 (3)	0.0156 (3)	0.0140 (3)	−0.0028 (2)	−0.0035 (2)	−0.0036 (2)
C12	0.0152 (3)	0.0180 (3)	0.0153 (3)	−0.0025 (2)	−0.0036 (2)	−0.0054 (2)
C13	0.0157 (3)	0.0149 (3)	0.0151 (3)	−0.0014 (2)	−0.0049 (2)	−0.0042 (2)
C14	0.0170 (3)	0.0189 (3)	0.0161 (3)	−0.0016 (2)	−0.0040 (2)	−0.0054 (2)
C15	0.0225 (3)	0.0214 (3)	0.0162 (3)	0.0002 (3)	−0.0047 (3)	−0.0076 (3)
C16	0.0265 (4)	0.0213 (3)	0.0207 (3)	−0.0010 (3)	−0.0099 (3)	−0.0087 (3)
C17	0.0226 (4)	0.0206 (3)	0.0231 (4)	−0.0050 (3)	−0.0104 (3)	−0.0048 (3)
C18	0.0180 (3)	0.0190 (3)	0.0182 (3)	−0.0039 (2)	−0.0060 (3)	−0.0037 (2)
C19	0.0165 (3)	0.0183 (3)	0.0160 (3)	−0.0045 (2)	−0.0007 (2)	−0.0070 (2)
C20	0.0200 (3)	0.0191 (3)	0.0196 (3)	−0.0020 (3)	−0.0025 (3)	−0.0065 (3)
C21	0.0220 (4)	0.0198 (3)	0.0249 (4)	−0.0023 (3)	0.0004 (3)	−0.0089 (3)
C22	0.0237 (4)	0.0251 (4)	0.0257 (4)	−0.0073 (3)	0.0036 (3)	−0.0140 (3)
C23	0.0239 (4)	0.0377 (5)	0.0240 (4)	−0.0064 (3)	−0.0012 (3)	−0.0182 (3)
C24	0.0198 (4)	0.0321 (4)	0.0212 (4)	−0.0022 (3)	−0.0038 (3)	−0.0143 (3)

O1—C7	1.2305 (9)	C11—C13	1.4742 (10)
N1—C12	1.3508 (10)	C12—H12A	0.9500
N1—N2	1.3661 (8)	C13—C18	1.3985 (11)
N1—C19	1.4232 (9)	C13—C14	1.4016 (11)
N2—C11	1.3325 (10)	C14—C15	1.3921 (10)
C1—C2	1.3906 (11)	C14—H14A	0.9500
C1—C6	1.3995 (11)	C15—C16	1.3939 (12)
C1—H1A	0.9500	C15—H15A	0.9500
C2—C3	1.3904 (12)	C16—C17	1.3903 (13)
C2—H2A	0.9500	C16—H16A	0.9500
C3—C4	1.3883 (13)	C17—C18	1.3926 (11)
C3—H3A	0.9500	C17—H17A	0.9500
C4—C5	1.3935 (11)	C18—H18A	0.9500
C4—H4A	0.9500	C19—C24	1.3918 (11)
C5—C6	1.3989 (11)	C19—C20	1.3930 (11)
C5—H5A	0.9500	C20—C21	1.3936 (11)
C6—C7	1.4978 (10)	C20—H20A	0.9500
C7—C8	1.4742 (11)	C21—C22	1.3892 (13)
C8—C9	1.3496 (10)	C21—H21A	0.9500
C8—H8A	0.9500	C22—C23	1.3885 (14)
C9—C10	1.4416 (10)	C22—H22A	0.9500
C9—H9A	0.9500	C23—C24	1.3937 (12)
C10—C12	1.3886 (10)	C23—H23A	0.9500
C10—C11	1.4305 (10)	C24—H24A	0.9500
C12—N1—N2	111.99 (6)	N1—C12—H12A	126.2
C12—N1—C19	127.99 (6)	C10—C12—H12A	126.2
N2—N1—C19	119.98 (6)	C18—C13—C14	119.08 (7)
C11—N2—N1	105.17 (6)	C18—C13—C11	120.35 (7)
C2—C1—C6	120.43 (7)	C14—C13—C11	120.39 (7)
C2—C1—H1A	119.8	C15—C14—C13	120.62 (7)
C6—C1—H1A	119.8	C15—C14—H14A	119.7
C3—C2—C1	120.10 (7)	C13—C14—H14A	119.7
C3—C2—H2A	119.9	C14—C15—C16	119.86 (8)
C1—C2—H2A	119.9	C14—C15—H15A	120.1
C4—C3—C2	119.96 (7)	C16—C15—H15A	120.1
C4—C3—H3A	120.0	C17—C16—C15	119.82 (7)
C2—C3—H3A	120.0	C17—C16—H16A	120.1
C3—C4—C5	120.16 (8)	C15—C16—H16A	120.1
C3—C4—H4A	119.9	C16—C17—C18	120.51 (7)
C5—C4—H4A	119.9	C16—C17—H17A	119.7
C4—C5—C6	120.30 (7)	C18—C17—H17A	119.7
C4—C5—H5A	119.8	C17—C18—C13	120.11 (7)
C6—C5—H5A	119.8	C17—C18—H18A	119.9
C5—C6—C1	119.04 (7)	C13—C18—H18A	119.9
C5—C6—C7	122.63 (7)	C24—C19—C20	120.83 (7)
C1—C6—C7	118.34 (6)	C24—C19—N1	119.87 (7)
O1—C7—C8	121.76 (7)	C20—C19—N1	119.30 (7)
O1—C7—C6	119.81 (7)	C19—C20—C21	119.29 (8)
C8—C7—C6	118.43 (6)	C19—C20—H20A	120.4
C9—C8—C7	120.44 (7)	C21—C20—H20A	120.4
C9—C8—H8A	119.8	C22—C21—C20	120.50 (8)
C7—C8—H8A	119.8	C22—C21—H21A	119.7
C8—C9—C10	128.27 (7)	C20—C21—H21A	119.7
C8—C9—H9A	115.9	C23—C22—C21	119.52 (8)
C10—C9—H9A	115.9	C23—C22—H22A	120.2
C12—C10—C11	103.95 (6)	C21—C22—H22A	120.2
C12—C10—C9	123.14 (7)	C22—C23—C24	120.88 (8)
C11—C10—C9	132.89 (7)	C22—C23—H23A	119.6
N2—C11—C10	111.32 (6)	C24—C23—H23A	119.6
N2—C11—C13	117.90 (6)	C19—C24—C23	118.96 (8)
C10—C11—C13	130.69 (7)	C19—C24—H24A	120.5
N1—C12—C10	107.56 (6)	C23—C24—H24A	120.5
C12—N1—N2—C11	0.28 (8)	C11—C10—C12—N1	0.79 (8)
C19—N1—N2—C11	178.30 (7)	C9—C10—C12—N1	−178.05 (7)
C6—C1—C2—C3	−0.03 (13)	N2—C11—C13—C18	−47.06 (10)
C1—C2—C3—C4	0.94 (13)	C10—C11—C13—C18	136.80 (8)
C2—C3—C4—C5	−1.00 (14)	N2—C11—C13—C14	128.07 (8)
C3—C4—C5—C6	0.15 (14)	C10—C11—C13—C14	−48.06 (11)
C4—C5—C6—C1	0.76 (12)	C18—C13—C14—C15	0.52 (11)
C4—C5—C6—C7	−179.03 (8)	C11—C13—C14—C15	−174.68 (7)
C2—C1—C6—C5	−0.82 (12)	C13—C14—C15—C16	−0.10 (12)
C2—C1—C6—C7	178.98 (7)	C14—C15—C16—C17	−0.59 (12)
C5—C6—C7—O1	−162.50 (8)	C15—C16—C17—C18	0.85 (12)
C1—C6—C7—O1	17.72 (11)	C16—C17—C18—C13	−0.43 (12)
C5—C6—C7—C8	17.37 (11)	C14—C13—C18—C17	−0.26 (11)
C1—C6—C7—C8	−162.41 (7)	C11—C13—C18—C17	174.95 (7)
O1—C7—C8—C9	6.89 (12)	C12—N1—C19—C24	−10.42 (12)
C6—C7—C8—C9	−172.98 (7)	N2—N1—C19—C24	171.91 (7)
C7—C8—C9—C10	−179.26 (7)	C12—N1—C19—C20	169.10 (8)
C8—C9—C10—C12	171.25 (8)	N2—N1—C19—C20	−8.57 (11)
C8—C9—C10—C11	−7.21 (14)	C24—C19—C20—C21	−0.83 (12)
N1—N2—C11—C10	0.25 (8)	N1—C19—C20—C21	179.65 (7)
N1—N2—C11—C13	−176.60 (6)	C19—C20—C21—C22	0.74 (13)
C12—C10—C11—N2	−0.66 (9)	C20—C21—C22—C23	0.16 (13)
C9—C10—C11—N2	178.01 (8)	C21—C22—C23—C24	−1.00 (14)
C12—C10—C11—C13	175.68 (8)	C20—C19—C24—C23	0.02 (13)
C9—C10—C11—C13	−5.65 (14)	N1—C19—C24—C23	179.53 (8)
N2—N1—C12—C10	−0.70 (9)	C22—C23—C24—C19	0.91 (14)
C19—N1—C12—C10	−178.53 (7)

Cg2 and Cg3 are the centroids of the C20–C25 and C13–C18 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12A···O1i	0.95	2.27	3.2019 (11)	167
C15—H15A···Cg2ii	0.95	2.81	3.6171 (9)	143
C2—H2A···Cg3iii	0.95	2.63	3.4304 (9)	143

Table 1

Hydrogen-bond geometry (Å, °)

Cg2 and Cg3 are the centroids of the C20–C25 and C13–C18 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C12—H12A⋯O1i	0.95	2.27	3.2019 (11)	167
C15—H15A⋯Cg2ii	0.95	2.81	3.6171 (9)	143
C2—H2A⋯Cg3iii	0.95	2.63	3.4304 (9)	143

Symmetry codes: (i) ; (ii) ; (iii) .