(E)-3-Phenyl-3-(3-phenyl-1H-1-pyrazol-yl)-2-propenal.

In the title compound C(18)H(14)N(2)O, the pendant rings make dihedral angles of 66.1 (1)° and 13.9 (1) with the central ring. In the crystal, two mol-ecules form a cyclic centrosymmetric R(2) (2)(22) dimer through pairs of C-H⋯O bonds. These dimers are further connected into zigzag chains extending along the b axis through C-H⋯π and C-H⋯O inter-actions.

Related literature

For the pharmacological and medicinal properties of the title compound, see: Baraldi et al. (1998 ▶); Bruno et al. (1990 ▶); Chen & Li (1998 ▶); Cottineau et al. (2002 ▶); Londershausen (1996 ▶); Mishra et al. (1998 ▶); Smith et al. (2001 ▶). For hybridization and electron delocalization, see: Beddoes et al. (1986 ▶); Jin et al. (2004 ▶). For ring and chain motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C18H14N2O

M = 274.31

Monoclinic,

a = 8.6157 (7) Å

b = 18.0969 (12) Å

c = 10.0861 (6) Å

β = 113.091 (6)°

V = 1446.61 (19) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 293 K

0.23 × 0.21 × 0.18 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2001 ▶) T min = 0.863, T max = 0.994

13719 measured reflections

2547 independent reflections

2262 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.105

S = 1.05

2547 reflections

190 parameters

H-atom parameters constrained

Δρmax = 0.14 e Å−3

Δρmin = −0.15 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL/PC (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL/PC; molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXTL/PC.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810004332/fj2268sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810004332/fj2268Isup2.hkl

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

C18H14N2O	F(000) = 576
Mr = 274.31	Dx = 1.260 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5126 reflections
a = 8.6157 (7) Å	θ = 1.7–27.6°
b = 18.0969 (12) Å	µ = 0.08 mm−1
c = 10.0861 (6) Å	T = 293 K
β = 113.091 (6)°	Block, colourless
V = 1446.61 (19) Å3	0.23 × 0.21 × 0.18 mm
Z = 4

Bruker SMART APEX CCD area-detector diffractometer	2547 independent reflections
Radiation source: fine-focus sealed tube	2262 reflections with I > 2σ(I)
graphite	Rint = 0.024
ω scans	θmax = 25.0°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 2001)	h = −10→10
Tmin = 0.863, Tmax = 0.994	k = −21→21
13719 measured reflections	l = −11→11

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.105	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0509P)2 + 0.2744P] where P = (Fo2 + 2Fc2)/3
2547 reflections	(Δ/σ)max = 0.001
190 parameters	Δρmax = 0.14 e Å−3
0 restraints	Δρmin = −0.14 e Å−3

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'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 > σ(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	0.61426 (14)	0.02209 (6)	0.24676 (12)	0.0463 (3)
N2	0.74924 (13)	−0.01152 (6)	0.23393 (12)	0.0447 (3)
C3	0.81474 (17)	−0.05400 (8)	0.34980 (14)	0.0467 (3)
C4	0.7236 (2)	−0.04724 (11)	0.43775 (17)	0.0663 (5)
H4	0.7448	−0.0712	0.5247	0.080*
C5	0.5990 (2)	0.00119 (10)	0.37010 (17)	0.0649 (5)
H5	0.5172	0.0174	0.4022	0.078*
C11	0.52083 (16)	0.07517 (7)	0.14569 (14)	0.0432 (3)
C12	0.36253 (17)	0.10037 (7)	0.15681 (14)	0.0442 (3)
C13	0.3380 (2)	0.17479 (9)	0.17313 (18)	0.0573 (4)
H13	0.4230	0.2085	0.1821	0.069*
C14	0.1874 (2)	0.19915 (10)	0.17617 (19)	0.0690 (5)
H14	0.1716	0.2493	0.1871	0.083*
C15	0.0613 (2)	0.14992 (10)	0.16317 (18)	0.0653 (5)
H15	−0.0406	0.1667	0.1633	0.078*
C16	0.08564 (19)	0.07612 (10)	0.14998 (17)	0.0595 (4)
H16	0.0008	0.0427	0.1428	0.071*
C17	0.23541 (18)	0.05101 (8)	0.14726 (15)	0.0510 (4)
H17	0.2513	0.0007	0.1390	0.061*
C31	0.96351 (17)	−0.09984 (7)	0.37111 (16)	0.0478 (4)
C32	1.0553 (2)	−0.13183 (9)	0.50393 (17)	0.0626 (4)
H32	1.0215	−0.1250	0.5801	0.075*
C33	1.1966 (2)	−0.17376 (10)	0.5237 (2)	0.0757 (5)
H33	1.2567	−0.1955	0.6128	0.091*
C34	1.2482 (2)	−0.18350 (11)	0.4134 (3)	0.0815 (6)
H34	1.3454	−0.2106	0.4281	0.098*
C35	1.1569 (2)	−0.15340 (10)	0.2805 (2)	0.0772 (5)
H35	1.1913	−0.1608	0.2048	0.093*
C36	1.0147 (2)	−0.11233 (9)	0.25925 (19)	0.0598 (4)
H36	0.9524	−0.0928	0.1686	0.072*
C1A	0.57622 (17)	0.10007 (8)	0.04689 (15)	0.0483 (3)
H1A	0.6831	0.0854	0.0552	0.058*
C2A	0.48155 (19)	0.14796 (8)	−0.07132 (16)	0.0524 (4)
H2A	0.3733	0.1617	−0.0819	0.063*
O1	0.53501 (16)	0.17125 (7)	−0.15736 (13)	0.0747 (4)

	U11	U22	U33	U12	U13	U23
N1	0.0437 (6)	0.0521 (7)	0.0449 (6)	0.0073 (5)	0.0193 (5)	0.0021 (5)
N2	0.0409 (6)	0.0464 (7)	0.0471 (7)	0.0035 (5)	0.0174 (5)	−0.0006 (5)
C3	0.0451 (8)	0.0474 (8)	0.0438 (8)	0.0006 (6)	0.0133 (6)	0.0000 (6)
C4	0.0683 (10)	0.0862 (12)	0.0498 (9)	0.0222 (9)	0.0291 (8)	0.0186 (8)
C5	0.0647 (10)	0.0859 (12)	0.0543 (9)	0.0226 (9)	0.0344 (8)	0.0143 (8)
C11	0.0404 (7)	0.0424 (7)	0.0439 (7)	−0.0005 (6)	0.0136 (6)	−0.0044 (6)
C12	0.0424 (7)	0.0479 (8)	0.0406 (7)	0.0033 (6)	0.0147 (6)	−0.0014 (6)
C13	0.0544 (9)	0.0491 (8)	0.0668 (10)	0.0023 (7)	0.0221 (8)	−0.0055 (7)
C14	0.0715 (11)	0.0548 (10)	0.0816 (12)	0.0193 (8)	0.0312 (9)	−0.0035 (8)
C15	0.0508 (9)	0.0807 (12)	0.0679 (11)	0.0188 (8)	0.0270 (8)	0.0051 (9)
C16	0.0470 (8)	0.0715 (11)	0.0627 (10)	0.0010 (7)	0.0244 (7)	0.0055 (8)
C17	0.0495 (8)	0.0499 (8)	0.0554 (9)	0.0015 (6)	0.0227 (7)	−0.0002 (7)
C31	0.0434 (8)	0.0411 (7)	0.0539 (8)	−0.0011 (6)	0.0137 (6)	−0.0006 (6)
C32	0.0595 (10)	0.0632 (10)	0.0544 (9)	0.0050 (8)	0.0106 (8)	0.0007 (7)
C33	0.0610 (11)	0.0675 (11)	0.0761 (12)	0.0148 (9)	0.0025 (9)	0.0085 (9)
C34	0.0601 (11)	0.0664 (11)	0.1134 (17)	0.0207 (9)	0.0290 (11)	0.0097 (11)
C35	0.0775 (12)	0.0679 (11)	0.1003 (15)	0.0211 (9)	0.0500 (11)	0.0127 (10)
C36	0.0612 (10)	0.0552 (9)	0.0675 (10)	0.0123 (7)	0.0301 (8)	0.0106 (7)
C1A	0.0406 (7)	0.0501 (8)	0.0541 (8)	0.0016 (6)	0.0186 (6)	0.0003 (6)
C2A	0.0518 (8)	0.0488 (8)	0.0570 (9)	−0.0003 (7)	0.0216 (7)	0.0008 (7)
O1	0.0825 (9)	0.0766 (8)	0.0753 (8)	0.0041 (6)	0.0420 (7)	0.0219 (6)

N1—C5	1.3552 (19)	C16—C17	1.378 (2)
N1—N2	1.3627 (15)	C16—H16	0.9300
N1—C11	1.4023 (18)	C17—H17	0.9300
N2—C3	1.3259 (17)	C31—C36	1.382 (2)
C3—C4	1.402 (2)	C31—C32	1.387 (2)
C3—C31	1.470 (2)	C32—C33	1.380 (2)
C4—C5	1.346 (2)	C32—H32	0.9300
C4—H4	0.9300	C33—C34	1.363 (3)
C5—H5	0.9300	C33—H33	0.9300
C11—C1A	1.340 (2)	C34—C35	1.373 (3)
C11—C12	1.4835 (18)	C34—H34	0.9300
C12—C13	1.383 (2)	C35—C36	1.376 (2)
C12—C17	1.387 (2)	C35—H35	0.9300
C13—C14	1.381 (2)	C36—H36	0.9300
C13—H13	0.9300	C1A—C2A	1.440 (2)
C14—C15	1.371 (3)	C1A—H1A	0.9300
C14—H14	0.9300	C2A—O1	1.2068 (18)
C15—C16	1.366 (2)	C2A—H2A	0.9300
C15—H15	0.9300
C5—N1—N2	110.89 (11)	C15—C16—H16	119.8
C5—N1—C11	128.59 (12)	C17—C16—H16	119.8
N2—N1—C11	120.31 (11)	C16—C17—C12	120.40 (14)
C3—N2—N1	105.02 (11)	C16—C17—H17	119.8
N2—C3—C4	110.90 (13)	C12—C17—H17	119.8
N2—C3—C31	120.10 (13)	C36—C31—C32	118.46 (14)
C4—C3—C31	129.01 (13)	C36—C31—C3	120.81 (13)
C5—C4—C3	105.64 (14)	C32—C31—C3	120.73 (14)
C5—C4—H4	127.2	C33—C32—C31	120.37 (17)
C3—C4—H4	127.2	C33—C32—H32	119.8
C4—C5—N1	107.55 (14)	C31—C32—H32	119.8
C4—C5—H5	126.2	C34—C33—C32	120.31 (17)
N1—C5—H5	126.2	C34—C33—H33	119.8
C1A—C11—N1	120.03 (12)	C32—C33—H33	119.8
C1A—C11—C12	123.97 (13)	C33—C34—C35	120.04 (17)
N1—C11—C12	116.00 (12)	C33—C34—H34	120.0
C13—C12—C17	118.80 (13)	C35—C34—H34	120.0
C13—C12—C11	119.78 (13)	C34—C35—C36	120.04 (18)
C17—C12—C11	121.40 (12)	C34—C35—H35	120.0
C14—C13—C12	120.15 (15)	C36—C35—H35	120.0
C14—C13—H13	119.9	C35—C36—C31	120.73 (16)
C12—C13—H13	119.9	C35—C36—H36	119.6
C15—C14—C13	120.42 (16)	C31—C36—H36	119.6
C15—C14—H14	119.8	C11—C1A—C2A	124.51 (13)
C13—C14—H14	119.8	C11—C1A—H1A	117.7
C16—C15—C14	119.87 (15)	C2A—C1A—H1A	117.7
C16—C15—H15	120.1	O1—C2A—C1A	123.61 (14)
C14—C15—H15	120.1	O1—C2A—H2A	118.2
C15—C16—C17	120.33 (16)	C1A—C2A—H2A	118.2
C5—N1—N2—C3	0.88 (16)	C13—C14—C15—C16	1.3 (3)
C11—N1—N2—C3	175.96 (12)	C14—C15—C16—C17	−1.1 (3)
N1—N2—C3—C4	−0.64 (16)	C15—C16—C17—C12	−0.5 (2)
N1—N2—C3—C31	179.26 (12)	C13—C12—C17—C16	1.8 (2)
N2—C3—C4—C5	0.2 (2)	C11—C12—C17—C16	−176.44 (13)
C31—C3—C4—C5	−179.71 (15)	N2—C3—C31—C36	−14.4 (2)
C3—C4—C5—N1	0.4 (2)	C4—C3—C31—C36	165.51 (16)
N2—N1—C5—C4	−0.8 (2)	N2—C3—C31—C32	165.91 (14)
C11—N1—C5—C4	−175.36 (15)	C4—C3—C31—C32	−14.2 (2)
C5—N1—C11—C1A	165.51 (15)	C36—C31—C32—C33	1.4 (2)
N2—N1—C11—C1A	−8.60 (19)	C3—C31—C32—C33	−178.88 (15)
C5—N1—C11—C12	−14.5 (2)	C31—C32—C33—C34	0.7 (3)
N2—N1—C11—C12	171.43 (11)	C32—C33—C34—C35	−1.9 (3)
C1A—C11—C12—C13	−56.2 (2)	C33—C34—C35—C36	1.1 (3)
N1—C11—C12—C13	123.79 (15)	C34—C35—C36—C31	1.1 (3)
C1A—C11—C12—C17	122.03 (16)	C32—C31—C36—C35	−2.3 (2)
N1—C11—C12—C17	−58.00 (17)	C3—C31—C36—C35	178.02 (15)
C17—C12—C13—C14	−1.6 (2)	N1—C11—C1A—C2A	172.66 (13)
C11—C12—C13—C14	176.68 (14)	C12—C11—C1A—C2A	−7.4 (2)
C12—C13—C14—C15	0.0 (3)	C11—C1A—C2A—O1	178.19 (15)

Cg is the centroid of the C31–C36 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C35—H35···O1i	0.93	2.59	3.358 (2)	140
C13—H13···O1ii	0.93	2.66	3.360 (2)	133
C14—H14···Cgiii	0.93	2.95	3.703 (2)	139

Table 1

Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C31–C36 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C35—H35⋯O1i	0.93	2.59	3.358 (2)	140
C13—H13⋯O1ii	0.93	2.66	3.360 (2)	133
C14—H14⋯Cgiii	0.93	2.95	3.703 (2)	139

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