(E)-5-Phenyl-N'-(1-phenyl-ethyl-idene)-1H-pyrazole-3-carbohydrazide.

In the mol-ecule of the title compound, C(18)H(16)N(4)O, the intra-molecular N-H⋯N hydrogen bond results in the formation of a planar five-membered ring, which is also co-planar with the adjacent five-membered ring, being oriented at a dihedral angle of 1.23 (3)°. The dihedral angles formed by the planar pyrazole ring with the adjacent phenyl ring and the other phenyl ring are 7.29 and 11.21°, respectively. The dihedral angle between the two phenyl rings is 18.07°. In the crystal structure, inter-molecular N-H⋯O hydrogen bonds link the mol-ecules.

Related literature

For general background, see: Ogretir et al. (2006 ▶); Tarafder et al. (2000 ▶); Deschamps et al. (2003 ▶); Wu et al. (2006 ▶). For related literature, see: Yang & Raptis (2003 ▶); Ali et al. (2005 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C18H16N4O

M = 304.35

Tetragonal,

a = 8.0190 (11) Å

c = 24.147 (5) Å

V = 1552.8 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 294 (2) K

0.25 × 0.20 × 0.18 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: none

3737 measured reflections

1686 independent reflections

1017 reflections with I > 2σ(I)

R int = 0.081

3 standard reflections every 100 reflections intensity decay: 4.1%

Refinement

R[F 2 > 2σ(F 2)] = 0.054

wR(F 2) = 0.143

S = 1.04

1686 reflections

209 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.19 e Å−3

Δρmin = −0.32 e Å−3

Data collection: CAD-4 Software (Enraf–Nonius, 1989 ▶); cell refinement: CAD-4 Software; data reduction: NRCVAX (Gabe et al., 1989 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 ▶); molecular graphics: SHELXTL/PC (Siemens, 1990 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680706223X/hk2398sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680706223X/hk2398Isup2.hkl

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

C18H16N4O	Z = 4
Mr = 304.35	F000 = 640
Tetragonal, P43	Dx = 1.302 Mg m−3
Hall symbol: P 4cw	Mo Kα radiation λ = 0.71073 Å
a = 8.0190 (11) Å	Cell parameters from 25 reflections
b = 8.0190 (11) Å	θ = 1–25º
c = 24.147 (5) Å	µ = 0.08 mm−1
α = 90º	T = 294 (2) K
β = 90º	Block, yellow
γ = 90º	0.25 × 0.20 × 0.18 mm
V = 1552.8 (4) Å3

Enraf–Nonius CAD-4 diffractometer	Rint = 0.081
Radiation source: fine-focus sealed tube	θmax = 26.9º
Monochromator: graphite	θmin = 2.5º
T = 294(2) K	h = 0→9
ω scans	k = 0→9
Absorption correction: none	l = −28→28
3737 measured reflections	3 standard reflections
1686 independent reflections	every 100 reflections
1017 reflections with I > 2σ(I)	intensity decay: 4.1%

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)] = 0.054	H-atom parameters constrained
wR(F2) = 0.143	w = 1/[σ2(Fo2) + (0.0792P)2] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max < 0.001
1686 reflections	Δρmax = 0.19 e Å−3
209 parameters	Δρmin = −0.32 e Å−3
1 restraint	Extinction correction: none
Primary atom site location: structure-invariant direct methods

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
O1	0.6526 (4)	0.7885 (4)	0.19156 (14)	0.0530 (9)
N1	0.8996 (5)	0.5984 (5)	0.14452 (17)	0.0484 (9)
N2	0.7574 (4)	0.6473 (5)	0.11695 (18)	0.0495 (10)
H2A	0.7423	0.6186	0.0830	0.059*
N3	0.4872 (4)	0.7339 (5)	0.05571 (16)	0.0477 (10)
N4	0.3421 (5)	0.7929 (5)	0.03787 (17)	0.0467 (9)
H4A	0.3060	0.7777	0.0047	0.056*
C1	1.2768 (6)	0.3604 (6)	0.1231 (3)	0.0600 (14)
H1B	1.2546	0.3129	0.0888	0.072*
C2	1.4206 (7)	0.3174 (7)	0.1507 (3)	0.0700 (16)
H2B	1.4918	0.2381	0.1355	0.084*
C3	1.4605 (6)	0.3911 (7)	0.2008 (3)	0.0615 (14)
H3B	1.5600	0.3658	0.2187	0.074*
C4	1.3495 (7)	0.5025 (7)	0.2236 (2)	0.0624 (14)
H4B	1.3737	0.5505	0.2578	0.075*
C5	1.2040 (6)	0.5445 (6)	0.1972 (2)	0.0547 (13)
H5A	1.1314	0.6203	0.2135	0.066*
C6	1.1639 (5)	0.4735 (6)	0.1456 (2)	0.0445 (11)
C7	1.0116 (6)	0.5222 (5)	0.1161 (2)	0.0427 (10)
C8	0.9950 (7)	0.4862 (7)	0.0543 (2)	0.0612 (14)
H8A	0.9620	0.5861	0.0354	0.092*
H8B	0.9123	0.4013	0.0487	0.092*
H8C	1.1002	0.4485	0.0401	0.092*
C9	0.6421 (6)	0.7398 (5)	0.1432 (2)	0.0445 (11)
C10	0.4972 (5)	0.7848 (5)	0.10870 (19)	0.0401 (9)
C11	0.3586 (5)	0.8767 (5)	0.12334 (19)	0.0424 (10)
H11A	0.3378	0.9267	0.1574	0.051*
C12	0.2562 (5)	0.8794 (5)	0.07682 (19)	0.0403 (10)
C13	0.0915 (5)	0.9501 (5)	0.06862 (18)	0.0384 (10)
C14	0.0112 (6)	0.9482 (7)	0.0169 (2)	0.0552 (13)
H14A	0.0658	0.9053	−0.0140	0.066*
C15	−0.1487 (7)	1.0101 (7)	0.0119 (3)	0.0645 (15)
H15A	−0.2025	1.0052	−0.0221	0.077*
C16	−0.2297 (6)	1.0789 (7)	0.0566 (2)	0.0594 (14)
H16A	−0.3361	1.1233	0.0525	0.071*
C17	−0.1517 (6)	1.0818 (7)	0.1080 (2)	0.0581 (13)
H17A	−0.2059	1.1264	0.1386	0.070*
C18	0.0066 (6)	1.0182 (6)	0.1129 (2)	0.0514 (12)
H18A	0.0584	1.0211	0.1474	0.062*

	U11	U22	U33	U12	U13	U23
O1	0.064 (2)	0.071 (2)	0.024 (2)	0.0045 (16)	−0.0093 (14)	−0.0017 (15)
N1	0.052 (2)	0.058 (2)	0.035 (3)	0.0014 (18)	−0.0090 (18)	0.0042 (18)
N2	0.052 (2)	0.066 (2)	0.030 (2)	0.0052 (19)	−0.0083 (18)	−0.0035 (19)
N3	0.048 (2)	0.062 (2)	0.033 (2)	0.0054 (18)	−0.0069 (17)	−0.0105 (17)
N4	0.050 (2)	0.061 (2)	0.029 (2)	0.0088 (18)	−0.0065 (17)	−0.0093 (17)
C1	0.056 (3)	0.071 (3)	0.053 (4)	0.002 (3)	−0.003 (3)	−0.012 (3)
C2	0.056 (3)	0.072 (4)	0.082 (5)	0.005 (3)	0.000 (3)	−0.011 (3)
C3	0.055 (3)	0.075 (3)	0.054 (4)	−0.003 (3)	−0.010 (3)	0.009 (3)
C4	0.067 (3)	0.075 (3)	0.044 (4)	−0.008 (3)	−0.008 (3)	0.004 (3)
C5	0.060 (3)	0.056 (3)	0.048 (4)	0.002 (2)	−0.007 (2)	−0.002 (2)
C6	0.045 (2)	0.045 (2)	0.043 (3)	−0.005 (2)	0.004 (2)	0.005 (2)
C7	0.047 (2)	0.052 (2)	0.029 (3)	−0.004 (2)	0.0008 (19)	−0.001 (2)
C8	0.067 (3)	0.076 (3)	0.041 (4)	0.004 (3)	0.001 (2)	−0.004 (2)
C9	0.053 (3)	0.050 (3)	0.031 (3)	−0.009 (2)	−0.004 (2)	0.003 (2)
C10	0.049 (2)	0.050 (2)	0.022 (2)	−0.003 (2)	−0.0065 (18)	−0.0004 (18)
C11	0.055 (3)	0.046 (2)	0.027 (3)	−0.001 (2)	−0.003 (2)	−0.0047 (18)
C12	0.049 (2)	0.047 (2)	0.024 (3)	−0.0011 (19)	−0.0063 (18)	−0.0003 (19)
C13	0.047 (2)	0.042 (2)	0.026 (3)	0.0015 (18)	0.0018 (18)	0.0020 (18)
C14	0.064 (3)	0.074 (3)	0.028 (3)	0.018 (3)	−0.005 (2)	−0.003 (2)
C15	0.068 (3)	0.095 (4)	0.031 (3)	0.022 (3)	−0.011 (2)	0.007 (3)
C16	0.054 (3)	0.075 (3)	0.049 (4)	0.015 (2)	0.001 (2)	0.012 (2)
C17	0.059 (3)	0.077 (3)	0.039 (3)	0.013 (3)	0.009 (2)	0.000 (2)
C18	0.060 (3)	0.068 (3)	0.026 (3)	0.000 (2)	0.002 (2)	−0.002 (2)

O1—C9	1.234 (6)	C7—C8	1.526 (7)
N1—C7	1.285 (6)	C8—H8A	0.9600
N1—N2	1.378 (5)	C8—H8B	0.9600
N2—C9	1.344 (6)	C8—H8C	0.9600
N2—H2A	0.8600	C9—C10	1.474 (6)
N3—N4	1.328 (5)	C10—C11	1.380 (6)
N3—C10	1.346 (6)	C11—C12	1.392 (6)
N4—C12	1.357 (6)	C11—H11A	0.9300
N4—H4A	0.8600	C12—C13	1.451 (6)
C1—C2	1.375 (8)	C13—C18	1.381 (7)
C1—C6	1.391 (7)	C13—C14	1.406 (7)
C1—H1B	0.9300	C14—C15	1.380 (7)
C2—C3	1.385 (8)	C14—H14A	0.9300
C2—H2B	0.9300	C15—C16	1.376 (8)
C3—C4	1.376 (8)	C15—H15A	0.9300
C3—H3B	0.9300	C16—C17	1.389 (7)
C4—C5	1.371 (7)	C16—H16A	0.9300
C4—H4B	0.9300	C17—C18	1.373 (7)
C5—C6	1.408 (7)	C17—H17A	0.9300
C5—H5A	0.9300	C18—H18A	0.9300
C6—C7	1.466 (7)
C7—N1—N2	117.2 (4)	H8A—C8—H8C	109.5
C9—N2—N1	119.9 (4)	H8B—C8—H8C	109.5
C9—N2—H2A	120.1	O1—C9—N2	125.0 (4)
N1—N2—H2A	120.1	O1—C9—C10	120.8 (4)
N4—N3—C10	104.6 (4)	N2—C9—C10	114.2 (4)
N3—N4—C12	113.7 (4)	N3—C10—C11	110.9 (4)
N3—N4—H4A	123.1	N3—C10—C9	120.7 (4)
C12—N4—H4A	123.1	C11—C10—C9	128.4 (4)
C2—C1—C6	121.4 (6)	C10—C11—C12	106.1 (4)
C2—C1—H1B	119.3	C10—C11—H11A	127.0
C6—C1—H1B	119.3	C12—C11—H11A	127.0
C1—C2—C3	120.6 (5)	N4—C12—C11	104.6 (4)
C1—C2—H2B	119.7	N4—C12—C13	124.6 (4)
C3—C2—H2B	119.7	C11—C12—C13	130.8 (4)
C4—C3—C2	118.5 (5)	C18—C13—C14	117.9 (4)
C4—C3—H3B	120.7	C18—C13—C12	119.8 (4)
C2—C3—H3B	120.7	C14—C13—C12	122.3 (4)
C5—C4—C3	121.6 (5)	C15—C14—C13	119.9 (5)
C5—C4—H4B	119.2	C15—C14—H14A	120.1
C3—C4—H4B	119.2	C13—C14—H14A	120.1
C4—C5—C6	120.5 (5)	C16—C15—C14	121.0 (5)
C4—C5—H5A	119.8	C16—C15—H15A	119.5
C6—C5—H5A	119.8	C14—C15—H15A	119.5
C1—C6—C5	117.4 (4)	C15—C16—C17	119.6 (5)
C1—C6—C7	121.8 (5)	C15—C16—H16A	120.2
C5—C6—C7	120.8 (4)	C17—C16—H16A	120.2
N1—C7—C6	116.8 (4)	C18—C17—C16	119.2 (5)
N1—C7—C8	123.4 (4)	C18—C17—H17A	120.4
C6—C7—C8	119.8 (4)	C16—C17—H17A	120.4
C7—C8—H8A	109.5	C17—C18—C13	122.3 (5)
C7—C8—H8B	109.5	C17—C18—H18A	118.8
H8A—C8—H8B	109.5	C13—C18—H18A	118.8
C7—C8—H8C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···N3	0.86	2.34	2.714 (2)	107
N4—H4A···O1i	0.86	1.98	2.788 (2)	157

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯N3	0.86	2.34	2.714 (2)	107
N4—H4A⋯O1i	0.86	1.98	2.788 (2)	157

Symmetry code: (i) .