1-(4-Chloro-phen-yl)-3-phenyl-1H-pyrazol-5(4H)-one.

In the crystal of the title compound, C(15)H(11)ClN(2)O, the molecules are linked by C-H⋯O and weak C-H⋯π inter-actions. The chloro-phenyl and phenyl rings are twisted with respect to the central pyrazolone ring, making dihedral angles of 18.23 (8) and 8.35 (8)°, respectively. The N-N and C=O bond lengths are comparable to those reported for pyrazolone compounds.

Related literature

For the properties and applications of pyrazolones and their derivatives, see: Bao et al. (2006 ▶); Bose et al. (2005 ▶); Ito et al. (2001 ▶); Li et al. (2000 ▶); Shi, et al. (2005 ▶); Whitaker (1995 ▶). For the synthesis, see: Jensen (1959 ▶). For related structures, see: Bovio et al. (1974 ▶); Dardonville et al. (1998 ▶); Ferretti et al. (1985 ▶); Holzer et al. (1999 ▶).

Experimental

Crystal data

C15H11ClN2O

M = 270.71

Monoclinic,

a = 11.2593 (4) Å

b = 12.1848 (4) Å

c = 9.5498 (3) Å

β = 103.053 (1)°

V = 1276.31 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.29 mm−1

T = 296 K

0.32 × 0.28 × 0.15 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

17039 measured reflections

3172 independent reflections

2578 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.111

S = 1.04

3172 reflections

172 parameters

H-atom parameters constrained

Δρmax = 0.23 e Å−3

Δρmin = −0.20 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809055263/dn2522sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809055263/dn2522Isup2.hkl

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

C15H11ClN2O	F(000) = 560.0
Mr = 270.71	Dx = 1.409 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 8730 reflections
a = 11.2593 (4) Å	θ = 2.5–28.4°
b = 12.1848 (4) Å	µ = 0.29 mm−1
c = 9.5498 (3) Å	T = 296 K
β = 103.053 (1)°	Block, yellow
V = 1276.31 (7) Å3	0.32 × 0.28 × 0.15 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	2578 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.021
graphite	θmax = 28.4°, θmin = 1.9°
φ and ω scans	h = −14→15
17039 measured reflections	k = −15→16
3172 independent reflections	l = −12→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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.111	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0526P)2 + 0.3591P] where P = (Fo2 + 2Fc2)/3
3172 reflections	(Δ/σ)max < 0.001
172 parameters	Δρmax = 0.23 e Å−3
0 restraints	Δρmin = −0.20 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
Cl1	0.49588 (4)	0.36865 (4)	0.10838 (4)	0.06295 (16)
N2	0.73364 (11)	0.53865 (9)	0.68321 (12)	0.0405 (3)
N1	0.75985 (10)	0.46368 (9)	0.79773 (12)	0.0396 (3)
C7	0.76387 (14)	0.64516 (11)	0.72628 (15)	0.0442 (3)
C8	0.82119 (14)	0.63688 (11)	0.88421 (15)	0.0434 (3)
H8A	0.9060	0.6593	0.9047	0.052*
H8B	0.7777	0.6811	0.9407	0.052*
C1	0.67906 (12)	0.49854 (11)	0.54432 (14)	0.0380 (3)
C4	0.56921 (13)	0.41944 (13)	0.27598 (14)	0.0445 (3)
O1	0.74620 (13)	0.72658 (9)	0.65145 (12)	0.0620 (3)
C5	0.56870 (15)	0.35700 (12)	0.39612 (16)	0.0491 (3)
H5	0.5317	0.2883	0.3866	0.059*
C10	0.85009 (12)	0.46390 (11)	1.05204 (14)	0.0392 (3)
C9	0.80911 (12)	0.51759 (11)	0.91237 (14)	0.0375 (3)
C3	0.62544 (16)	0.51956 (13)	0.28785 (16)	0.0538 (4)
H3	0.6260	0.5607	0.2060	0.065*
C15	0.82395 (14)	0.35388 (12)	1.07152 (17)	0.0476 (3)
H15	0.7787	0.3135	0.9952	0.057*
C6	0.62340 (13)	0.39676 (12)	0.53086 (15)	0.0448 (3)
H6	0.6228	0.3551	0.6123	0.054*
C11	0.91727 (14)	0.52294 (13)	1.16804 (15)	0.0481 (3)
H11	0.9340	0.5967	1.1569	0.058*
C13	0.93286 (17)	0.36390 (16)	1.31805 (18)	0.0617 (4)
H13	0.9606	0.3304	1.4069	0.074*
C2	0.68150 (16)	0.55939 (13)	0.42195 (16)	0.0531 (4)
H2	0.7209	0.6270	0.4303	0.064*
C12	0.95927 (16)	0.47258 (15)	1.29984 (16)	0.0582 (4)
H12	1.0054	0.5122	1.3763	0.070*
C14	0.86514 (16)	0.30462 (15)	1.20418 (18)	0.0594 (4)
H14	0.8472	0.2313	1.2168	0.071*

	U11	U22	U33	U12	U13	U23
Cl1	0.0769 (3)	0.0676 (3)	0.0378 (2)	0.0076 (2)	−0.00071 (18)	−0.01026 (16)
N2	0.0514 (6)	0.0331 (5)	0.0348 (5)	−0.0008 (5)	0.0052 (5)	0.0022 (4)
N1	0.0474 (6)	0.0345 (6)	0.0352 (5)	−0.0001 (5)	0.0058 (5)	0.0031 (4)
C7	0.0551 (8)	0.0358 (7)	0.0416 (7)	−0.0025 (6)	0.0108 (6)	−0.0011 (5)
C8	0.0559 (8)	0.0347 (7)	0.0392 (7)	−0.0025 (6)	0.0101 (6)	−0.0032 (5)
C1	0.0415 (7)	0.0371 (7)	0.0347 (6)	0.0030 (5)	0.0071 (5)	−0.0001 (5)
C4	0.0479 (7)	0.0494 (8)	0.0342 (6)	0.0093 (6)	0.0053 (5)	−0.0045 (6)
O1	0.0983 (9)	0.0359 (5)	0.0487 (6)	−0.0051 (5)	0.0098 (6)	0.0068 (5)
C5	0.0574 (9)	0.0413 (7)	0.0435 (7)	−0.0040 (6)	0.0007 (6)	−0.0003 (6)
C10	0.0409 (7)	0.0420 (7)	0.0354 (6)	0.0008 (5)	0.0100 (5)	0.0003 (5)
C9	0.0408 (6)	0.0354 (6)	0.0369 (6)	−0.0001 (5)	0.0099 (5)	−0.0018 (5)
C3	0.0736 (10)	0.0533 (9)	0.0353 (7)	−0.0010 (7)	0.0141 (7)	0.0050 (6)
C15	0.0506 (8)	0.0447 (8)	0.0452 (7)	−0.0065 (6)	0.0059 (6)	0.0028 (6)
C6	0.0535 (8)	0.0408 (7)	0.0370 (7)	−0.0022 (6)	0.0035 (6)	0.0048 (5)
C11	0.0593 (9)	0.0468 (8)	0.0380 (7)	−0.0041 (6)	0.0106 (6)	−0.0038 (6)
C13	0.0682 (10)	0.0733 (12)	0.0418 (8)	0.0019 (8)	0.0088 (7)	0.0161 (7)
C2	0.0733 (10)	0.0446 (8)	0.0422 (7)	−0.0109 (7)	0.0144 (7)	0.0013 (6)
C12	0.0662 (10)	0.0706 (11)	0.0355 (7)	−0.0048 (8)	0.0067 (7)	−0.0033 (7)
C14	0.0665 (10)	0.0543 (9)	0.0559 (9)	−0.0069 (8)	0.0106 (8)	0.0155 (7)

Cl1—C4	1.7406 (14)	C10—C11	1.3923 (19)
N2—C7	1.3806 (17)	C10—C15	1.394 (2)
N2—N1	1.4042 (15)	C10—C9	1.4635 (18)
N2—C1	1.4169 (16)	C3—C2	1.382 (2)
N1—C9	1.2897 (17)	C3—H3	0.9300
C7—O1	1.2126 (17)	C15—C14	1.384 (2)
C7—C8	1.504 (2)	C15—H15	0.9300
C8—C9	1.4900 (18)	C6—H6	0.9300
C8—H8A	0.9700	C11—C12	1.384 (2)
C8—H8B	0.9700	C11—H11	0.9300
C1—C6	1.3824 (19)	C13—C12	1.377 (3)
C1—C2	1.3894 (19)	C13—C14	1.382 (3)
C4—C3	1.367 (2)	C13—H13	0.9300
C4—C5	1.378 (2)	C2—H2	0.9300
C5—C6	1.383 (2)	C12—H12	0.9300
C5—H5	0.9300	C14—H14	0.9300
C7—N2—N1	112.65 (11)	N1—C9—C8	112.52 (11)
C7—N2—C1	128.96 (11)	C10—C9—C8	125.29 (12)
N1—N2—C1	118.37 (10)	C4—C3—C2	119.75 (14)
C9—N1—N2	107.72 (11)	C4—C3—H3	120.1
O1—C7—N2	126.65 (14)	C2—C3—H3	120.1
O1—C7—C8	128.47 (13)	C14—C15—C10	120.14 (15)
N2—C7—C8	104.88 (11)	C14—C15—H15	119.9
C9—C8—C7	102.15 (11)	C10—C15—H15	119.9
C9—C8—H8A	111.3	C1—C6—C5	119.88 (13)
C7—C8—H8A	111.3	C1—C6—H6	120.1
C9—C8—H8B	111.3	C5—C6—H6	120.1
C7—C8—H8B	111.3	C12—C11—C10	120.47 (15)
H8A—C8—H8B	109.2	C12—C11—H11	119.8
C6—C1—C2	119.68 (13)	C10—C11—H11	119.8
C6—C1—N2	119.22 (12)	C12—C13—C14	119.98 (15)
C2—C1—N2	121.10 (12)	C12—C13—H13	120.0
C3—C4—C5	120.84 (13)	C14—C13—H13	120.0
C3—C4—Cl1	120.53 (11)	C3—C2—C1	120.03 (14)
C5—C4—Cl1	118.63 (12)	C3—C2—H2	120.0
C4—C5—C6	119.79 (14)	C1—C2—H2	120.0
C4—C5—H5	120.1	C13—C12—C11	120.14 (16)
C6—C5—H5	120.1	C13—C12—H12	119.9
C11—C10—C15	118.94 (13)	C11—C12—H12	119.9
C11—C10—C9	119.80 (13)	C13—C14—C15	120.32 (16)
C15—C10—C9	121.26 (13)	C13—C14—H14	119.8
N1—C9—C10	122.18 (12)	C15—C14—H14	119.8
C7—N2—N1—C9	−1.81 (16)	C15—C10—C9—C8	173.39 (14)
C1—N2—N1—C9	179.69 (11)	C7—C8—C9—N1	1.93 (16)
N1—N2—C7—O1	−176.48 (15)	C7—C8—C9—C10	−179.50 (13)
C1—N2—C7—O1	1.8 (3)	C5—C4—C3—C2	−0.7 (2)
N1—N2—C7—C8	2.95 (16)	Cl1—C4—C3—C2	178.94 (13)
C1—N2—C7—C8	−178.75 (13)	C11—C10—C15—C14	−0.4 (2)
O1—C7—C8—C9	176.62 (16)	C9—C10—C15—C14	179.13 (14)
N2—C7—C8—C9	−2.79 (15)	C2—C1—C6—C5	−1.1 (2)
C7—N2—C1—C6	−160.62 (14)	N2—C1—C6—C5	179.36 (13)
N1—N2—C1—C6	17.60 (18)	C4—C5—C6—C1	−0.5 (2)
C7—N2—C1—C2	19.9 (2)	C15—C10—C11—C12	1.2 (2)
N1—N2—C1—C2	−161.90 (13)	C9—C10—C11—C12	−178.37 (13)
C3—C4—C5—C6	1.4 (2)	C4—C3—C2—C1	−1.0 (3)
Cl1—C4—C5—C6	−178.24 (12)	C6—C1—C2—C3	1.9 (2)
N2—N1—C9—C10	−178.86 (11)	N2—C1—C2—C3	−178.65 (14)
N2—N1—C9—C8	−0.24 (15)	C14—C13—C12—C11	0.6 (3)
C11—C10—C9—N1	171.35 (13)	C10—C11—C12—C13	−1.3 (3)
C15—C10—C9—N1	−8.2 (2)	C12—C13—C14—C15	0.2 (3)
C11—C10—C9—C8	−7.1 (2)	C10—C15—C14—C13	−0.3 (3)

Cg1 is the centroid of the C10–C15 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8B···O1i	0.97	2.40	3.3115 (19)	156
C8—H8A···Cg1ii	0.97	2.76	3.5026 (17)	134

Compound	C═O	N—N
C13H14N2O2a	1.313 (2)	1.395 (2)
C19H16N2O2a	1.261 (2)	1.404 (2)
C15H12N2O2Sa	1.246 (2)	1.373 (2)
C22H15ClN2Oc	1.228 (2)	1.405 (2)
C16H11N3Oc	1.252 (3)	1.412 (4)
C16H10ClN3Oc	1.250 (5)	1.420 (5)
C10H8N4O5d	1.207 (3)	1.412 (2)
C15H11ClN2Oe	1.213 (2)	1.404 (2)

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—H8B⋯O1i	0.97	2.40	3.3115 (19)	156
C8—H8A⋯Cg1ii	0.97	2.76	3.5026 (17)	134

Symmetry codes: (i) ; (ii) .

Table 2

Comparison of C=O and N—N bond lengths (Å) between the title compound and reported pyrazolone compounds.

Compound	C=O	N—N
C13H14N2O2a	1.313 (2)	1.395 (2)
C19H16N2O2a	1.261 (2)	1.404 (2)
C15H12N2O2Sa	1.246 (2)	1.373 (2)
C22H15ClN2Oc	1.228 (2)	1.405 (2)
C16H11N3Oc	1.252 (3)	1.412 (4)
C16H10ClN3Oc	1.250 (5)	1.420 (5)
C10H8N4O5d	1.207 (3)	1.412 (2)
C15H11ClN2Oe	1.213 (2)	1.404 (2)

Notes: (a) Holzer et al. (1999 ▶); (b) Bovio et al. (1974 ▶); (c) Ferretti et al. (1985 ▶); (d) Dardonville et al. (1998 ▶); (e) this work.