1,3-Diphenyl-4,5-dihydro-1H-pyrazol-5-one.

In the title pyrazolone derivative, C(15)H(12)N(2)O, the five-membered ring is approximately planar (r.m.s. deviation = 0.018 Å), and the N- and C-bound benzene rings are inclined to this plane [dihedral angles = 21.45 (10) and 6.96 (10)°, respectively] and form a dihedral angle of 20.42 (10)° with each other. Supra-molecular layers are formed in the crystal structure via C-H⋯O and C-H⋯N inter-actions, and these are assembled into double layers by C-H⋯π and π-π inter-actions between the pyrazole and C-bound benzene rings [ring centroid-centroid distance = 3.6476 (12) Å]. The double layers stack along the a axis being connected by π-π inter-actions between the N- and C-bound benzene rings [ring centroid-centroid distance = 3.7718 (12) Å].

Related literature

For the therapeutic importance of pyrazoles, see: Sil et al. (2005 ▶); Haddad et al. (2004 ▶). For their diverse pharmacological activities, see: Bekhit et al. (2012 ▶); Castagnolo et al. (2008 ▶); Ramajayam et al. (2010 ▶). For background to the synthesis, see: Nef (1891 ▶); Katritzky et al. (1997 ▶); Wardell et al. (2007 ▶); de Lima et al. (2010 ▶). For evaluation of tautomeric forms using NMR MO calculations and crystallography, see: Feeney et al. (1970 ▶); Hawkes et al. (1977 ▶); Freyer et al. (1983 ▶); Dardonville et al. (1998 ▶); Kleinpeter & Koch (2001 ▶); Bechtel et al. (1973a ▶,b ▶); Chmutova et al. (2001 ▶); Wardell et al. (2007 ▶); Gallardo et al. (2009 ▶); Ding & Zhao (2010 ▶). For a previous synthesis, see: Kimata et al. (2007 ▶). For a recently reported structure, see: Wardell et al. (2012 ▶).

Experimental

Crystal data

C15H12N2O

M = 236.27

Monoclinic,

a = 11.1823 (3) Å

b = 11.7503 (4) Å

c = 9.6443 (2) Å

β = 113.998 (2)°

V = 1157.68 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 120 K

0.34 × 0.10 × 0.08 mm

Data collection

Rigaku Saturn724+ diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2007 ▶) T min = 0.790, T max = 1.000

12058 measured reflections

2024 independent reflections

1829 reflections with I > 2σ(I)

R int = 0.042

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.127

S = 1.07

2024 reflections

163 parameters

H-atom parameters constrained

Δρmax = 0.74 e Å−3

Δρmin = −0.20 e Å−3

Data collection: COLLECT (Hooft, 1998 ▶); cell refinement: DENZO (Otwinowski & Minor, 1997 ▶) and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812009567/hg5186sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812009567/hg5186Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812009567/hg5186Isup3.cml

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

C15H12N2O	F(000) = 496
Mr = 236.27	Dx = 1.356 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9201 reflections
a = 11.1823 (3) Å	θ = 2.9–27.5°
b = 11.7503 (4) Å	µ = 0.09 mm−1
c = 9.6443 (2) Å	T = 120 K
β = 113.998 (2)°	Rod, light-yellow
V = 1157.68 (6) Å3	0.34 × 0.10 × 0.08 mm
Z = 4

Rigaku Saturn724+ diffractometer	2024 independent reflections
Radiation source: Rotating Anode	1829 reflections with I > 2σ(I)
Confocal monochromator	Rint = 0.042
Detector resolution: 28.5714 pixels mm-1	θmax = 25.0°, θmin = 2.9°
profile data from ω–scans	h = −13→13
Absorption correction: multi-scan (SADABS; Sheldrick, 2007)	k = −13→12
Tmin = 0.790, Tmax = 1.000	l = −11→11
12058 measured reflections

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.127	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.0598P)2 + 0.8279P] where P = (Fo2 + 2Fc2)/3
2024 reflections	(Δ/σ)max < 0.001
163 parameters	Δρmax = 0.74 e Å−3
0 restraints	Δρmin = −0.20 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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	0.22694 (13)	0.27778 (11)	0.57957 (14)	0.0312 (4)
N1	0.21383 (13)	0.47099 (12)	0.62331 (15)	0.0198 (4)
N2	0.24220 (13)	0.54258 (12)	0.74837 (15)	0.0196 (3)
C1	0.15405 (16)	0.51898 (14)	0.47568 (18)	0.0195 (4)
C2	0.16304 (18)	0.46485 (15)	0.35195 (19)	0.0247 (4)
H2	0.2084	0.3946	0.3650	0.030*
C3	0.1051 (2)	0.51443 (17)	0.2092 (2)	0.0302 (5)
H3	0.1101	0.4771	0.1243	0.036*
C4	0.03995 (18)	0.61747 (16)	0.1888 (2)	0.0292 (5)
H4	0.0002	0.6507	0.0907	0.035*
C5	0.03356 (17)	0.67148 (16)	0.3133 (2)	0.0272 (4)
H5	−0.0094	0.7429	0.3004	0.033*
C6	0.08893 (17)	0.62284 (15)	0.4563 (2)	0.0232 (4)
H6	0.0826	0.6600	0.5405	0.028*
C7	0.24708 (16)	0.35860 (14)	0.66481 (19)	0.0200 (4)
C8	0.30948 (17)	0.35961 (14)	0.83575 (18)	0.0202 (4)
H8A	0.2618	0.3096	0.8787	0.024*
H8B	0.4023	0.3357	0.8752	0.024*
C9	0.29726 (16)	0.48130 (14)	0.86983 (18)	0.0187 (4)
C10	0.34323 (16)	0.53258 (14)	1.02117 (18)	0.0204 (4)
C11	0.31799 (17)	0.64722 (15)	1.0390 (2)	0.0231 (4)
H11	0.2693	0.6921	0.9523	0.028*
C12	0.36371 (18)	0.69541 (16)	1.1822 (2)	0.0259 (4)
H12	0.3452	0.7729	1.1937	0.031*
C13	0.43659 (18)	0.63072 (16)	1.3092 (2)	0.0271 (4)
H13	0.4688	0.6642	1.4073	0.033*
C14	0.46240 (18)	0.51717 (16)	1.2925 (2)	0.0260 (4)
H14	0.5127	0.4731	1.3794	0.031*
C15	0.41501 (17)	0.46785 (15)	1.14959 (19)	0.0225 (4)
H15	0.4315	0.3897	1.1390	0.027*

	U11	U22	U33	U12	U13	U23
O1	0.0396 (8)	0.0244 (7)	0.0291 (7)	0.0014 (6)	0.0134 (6)	−0.0030 (6)
N1	0.0215 (7)	0.0188 (8)	0.0177 (7)	−0.0005 (6)	0.0064 (6)	−0.0021 (5)
N2	0.0202 (7)	0.0191 (8)	0.0195 (7)	−0.0009 (6)	0.0079 (6)	−0.0019 (5)
C1	0.0169 (8)	0.0201 (9)	0.0201 (9)	−0.0037 (6)	0.0061 (7)	0.0006 (7)
C2	0.0271 (9)	0.0236 (9)	0.0244 (9)	−0.0011 (7)	0.0113 (7)	0.0003 (7)
C3	0.0357 (11)	0.0335 (11)	0.0214 (9)	−0.0065 (8)	0.0117 (8)	−0.0026 (8)
C4	0.0280 (10)	0.0302 (10)	0.0225 (9)	−0.0072 (8)	0.0031 (8)	0.0067 (7)
C5	0.0235 (9)	0.0233 (9)	0.0294 (10)	−0.0014 (7)	0.0053 (7)	0.0042 (7)
C6	0.0216 (9)	0.0230 (9)	0.0243 (9)	−0.0013 (7)	0.0086 (7)	−0.0014 (7)
C7	0.0217 (9)	0.0170 (8)	0.0221 (9)	−0.0005 (7)	0.0099 (7)	−0.0007 (7)
C8	0.0231 (9)	0.0174 (9)	0.0207 (8)	0.0006 (7)	0.0094 (7)	0.0010 (7)
C9	0.0170 (8)	0.0201 (9)	0.0195 (8)	0.0000 (6)	0.0079 (7)	0.0015 (7)
C10	0.0191 (8)	0.0230 (9)	0.0214 (9)	−0.0013 (7)	0.0106 (7)	0.0000 (7)
C11	0.0214 (9)	0.0241 (9)	0.0233 (9)	0.0026 (7)	0.0086 (7)	0.0018 (7)
C12	0.0272 (9)	0.0235 (9)	0.0294 (10)	0.0012 (7)	0.0140 (8)	−0.0040 (7)
C13	0.0286 (10)	0.0316 (11)	0.0217 (9)	−0.0024 (8)	0.0108 (8)	−0.0062 (7)
C14	0.0273 (10)	0.0305 (10)	0.0199 (9)	0.0018 (8)	0.0093 (7)	0.0035 (7)
C15	0.0257 (9)	0.0205 (9)	0.0232 (9)	0.0012 (7)	0.0120 (7)	0.0016 (7)

O1—C7	1.216 (2)	C7—C8	1.506 (2)
N1—C7	1.386 (2)	C8—C9	1.486 (2)
N1—N2	1.3970 (19)	C8—H8A	0.9900
N1—C1	1.421 (2)	C8—H8B	0.9900
N2—C9	1.297 (2)	C9—C10	1.465 (2)
C1—C2	1.391 (2)	C10—C15	1.396 (2)
C1—C6	1.394 (2)	C10—C11	1.401 (2)
C2—C3	1.389 (3)	C11—C12	1.384 (2)
C2—H2	0.9500	C11—H11	0.9500
C3—C4	1.385 (3)	C12—C13	1.389 (3)
C3—H3	0.9500	C12—H12	0.9500
C4—C5	1.386 (3)	C13—C14	1.388 (3)
C4—H4	0.9500	C13—H13	0.9500
C5—C6	1.384 (2)	C14—C15	1.387 (2)
C5—H5	0.9500	C14—H14	0.9500
C6—H6	0.9500	C15—H15	0.9500
C7—N1—N2	112.61 (13)	C9—C8—H8A	111.4
C7—N1—C1	128.99 (14)	C7—C8—H8A	111.4
N2—N1—C1	118.38 (14)	C9—C8—H8B	111.4
C9—N2—N1	107.64 (14)	C7—C8—H8B	111.4
C2—C1—C6	120.06 (16)	H8A—C8—H8B	109.3
C2—C1—N1	120.63 (15)	N2—C9—C10	121.10 (15)
C6—C1—N1	119.29 (15)	N2—C9—C8	112.77 (14)
C3—C2—C1	119.40 (17)	C10—C9—C8	126.12 (15)
C3—C2—H2	120.3	C15—C10—C11	119.15 (15)
C1—C2—H2	120.3	C15—C10—C9	120.12 (16)
C4—C3—C2	120.92 (17)	C11—C10—C9	120.72 (15)
C4—C3—H3	119.5	C12—C11—C10	120.30 (16)
C2—C3—H3	119.5	C12—C11—H11	119.8
C3—C4—C5	119.12 (16)	C10—C11—H11	119.8
C3—C4—H4	120.4	C11—C12—C13	120.13 (17)
C5—C4—H4	120.4	C11—C12—H12	119.9
C6—C5—C4	120.94 (17)	C13—C12—H12	119.9
C6—C5—H5	119.5	C14—C13—C12	119.95 (16)
C4—C5—H5	119.5	C14—C13—H13	120.0
C5—C6—C1	119.52 (17)	C12—C13—H13	120.0
C5—C6—H6	120.2	C13—C14—C15	120.21 (16)
C1—C6—H6	120.2	C13—C14—H14	119.9
O1—C7—N1	126.50 (15)	C15—C14—H14	119.9
O1—C7—C8	128.48 (15)	C14—C15—C10	120.24 (17)
N1—C7—C8	105.00 (13)	C14—C15—H15	119.9
C9—C8—C7	101.91 (13)	C10—C15—H15	119.9
C7—N1—N2—C9	2.34 (18)	O1—C7—C8—C9	−176.47 (18)
C1—N1—N2—C9	−179.20 (14)	N1—C7—C8—C9	2.23 (16)
C7—N1—C1—C2	−23.6 (3)	N1—N2—C9—C10	177.90 (14)
N2—N1—C1—C2	158.25 (15)	N1—N2—C9—C8	−0.70 (18)
C7—N1—C1—C6	158.12 (17)	C7—C8—C9—N2	−0.98 (18)
N2—N1—C1—C6	−20.0 (2)	C7—C8—C9—C10	−179.50 (15)
C6—C1—C2—C3	−0.9 (3)	N2—C9—C10—C15	−172.87 (15)
N1—C1—C2—C3	−179.19 (15)	C8—C9—C10—C15	5.5 (3)
C1—C2—C3—C4	0.8 (3)	N2—C9—C10—C11	6.0 (2)
C2—C3—C4—C5	0.3 (3)	C8—C9—C10—C11	−175.62 (16)
C3—C4—C5—C6	−1.3 (3)	C15—C10—C11—C12	0.0 (3)
C4—C5—C6—C1	1.1 (3)	C9—C10—C11—C12	−178.90 (16)
C2—C1—C6—C5	0.0 (3)	C10—C11—C12—C13	0.9 (3)
N1—C1—C6—C5	178.26 (15)	C11—C12—C13—C14	−0.7 (3)
N2—N1—C7—O1	175.85 (16)	C12—C13—C14—C15	−0.4 (3)
C1—N1—C7—O1	−2.4 (3)	C13—C14—C15—C10	1.2 (3)
N2—N1—C7—C8	−2.88 (18)	C11—C10—C15—C14	−1.0 (3)
C1—N1—C7—C8	178.87 (15)	C9—C10—C15—C14	177.83 (16)

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8A···O1i	0.99	2.36	3.279 (2)	154
C12—H12···N2ii	0.95	2.61	3.527 (2)	163
C8—H8B···Cg1iii	0.99	2.69	3.437 (2)	132

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C10–C15 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8A⋯O1i	0.99	2.36	3.279 (2)	154
C12—H12⋯N2ii	0.95	2.61	3.527 (2)	163
C8—H8B⋯Cg1iii	0.99	2.69	3.437 (2)	132

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