3-(4-Chloro-phen-yl)-1-phenyl-1H-pyrazole-4-carbaldehyde.

In the title compound, C(16)H(11)ClN(2)O, the chloro-substituted phenyl ring is disordered over two positions with refined site occupancies of 0.503 (2) and 0.497 (2). The dihedral angle between the pyrazole and phenyl rings is 7.93 (7)°. The pyrazole ring also forms dihedral angles of 24.43 (9)° and 28.67 (9)° with the disordered chloro-substituted benzene ring. In the crystal, mol-ecules are linked by inter-molecular C-H⋯O hydrogen bonds, generating R(2) (1)(7) and R(2) (2)(10) ring motifs. π-π inter-actions between the pyrazole and phenyl rings [centroid-centroid distance = 3.758 (1) Å] further stabilize the crystal structure.

Related literature

For related pharmacological literature, see: Karci & Karci (2008 ▶); Isloor et al. (2000 ▶); Kalluraya et al. (2004 ▶); Isloor et al. (2009 ▶); Comber et al. (1992 ▶). For the experimental preparation, see: Vora et al. (2009 ▶). For reference bond-length data, see: Allen et al. (1987 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C16H11ClN2O

M = 282.72

Monoclinic,

a = 16.0429 (4) Å

b = 4.8585 (1) Å

c = 16.7960 (4) Å

β = 96.581 (1)°

V = 1300.53 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.29 mm−1

T = 100 K

0.55 × 0.16 × 0.08 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.858, T max = 0.979

26528 measured reflections

3859 independent reflections

3302 reflections with I > 2σ(I)

R int = 0.057

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.098

S = 1.03

3859 reflections

218 parameters

H-atom parameters constrained

Δρmax = 0.36 e Å−3

Δρmin = −0.35 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/S1600536811023713/wn2437sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811023713/wn2437Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811023713/wn2437Isup3.cml

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

C16H11ClN2O	F(000) = 584
Mr = 282.72	Dx = 1.444 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9960 reflections
a = 16.0429 (4) Å	θ = 2.4–30.2°
b = 4.8585 (1) Å	µ = 0.29 mm−1
c = 16.7960 (4) Å	T = 100 K
β = 96.581 (1)°	Needle, colourless
V = 1300.53 (5) Å3	0.55 × 0.16 × 0.08 mm
Z = 4

Bruker SMART APEXII CCD area-detector diffractometer	3859 independent reflections
Radiation source: fine-focus sealed tube	3302 reflections with I > 2σ(I)
graphite	Rint = 0.057
φ and ω scans	θmax = 30.2°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −22→22
Tmin = 0.858, Tmax = 0.979	k = −6→6
26528 measured reflections	l = −20→23

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) = 0.098	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0397P)2 + 0.6665P] where P = (Fo2 + 2Fc2)/3
3859 reflections	(Δ/σ)max < 0.001
218 parameters	Δρmax = 0.36 e Å−3
0 restraints	Δρmin = −0.35 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 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	Occ. (<1)
Cl1	−0.055017 (18)	−0.04423 (7)	0.181350 (19)	0.02215 (9)
O1	0.43582 (6)	−0.2143 (2)	0.07840 (6)	0.0270 (2)
N1	0.32027 (6)	0.4298 (2)	−0.06319 (6)	0.0180 (2)
N2	0.24330 (7)	0.4223 (2)	−0.03471 (7)	0.0190 (2)
C1	0.41332 (9)	0.6604 (3)	−0.14732 (9)	0.0241 (3)
H1A	0.4596	0.5576	−0.1225	0.029*
C2	0.42428 (9)	0.8515 (3)	−0.20713 (9)	0.0248 (3)
H2A	0.4785	0.8781	−0.2234	0.030*
C3	0.35726 (9)	1.0028 (3)	−0.24314 (8)	0.0238 (3)
H3A	0.3654	1.1322	−0.2840	0.029*
C4	0.27791 (9)	0.9645 (3)	−0.21919 (8)	0.0276 (3)
H4A	0.2318	1.0693	−0.2434	0.033*
C5	0.26568 (8)	0.7734 (3)	−0.15994 (8)	0.0245 (3)
H5A	0.2114	0.7462	−0.1439	0.029*
C6	0.33339 (8)	0.6232 (3)	−0.12461 (7)	0.0183 (2)
C7	0.37382 (8)	0.2434 (3)	−0.02733 (7)	0.0181 (2)
H7A	0.4300	0.2126	−0.0379	0.022*
C8	0.33170 (7)	0.1040 (3)	0.02808 (7)	0.0171 (2)
C9	0.24994 (7)	0.2247 (3)	0.02049 (7)	0.0167 (2)
C10	0.17600 (7)	0.1594 (3)	0.06219 (7)	0.0160 (2)
C13	0.03440 (7)	0.0390 (3)	0.13674 (7)	0.0158 (2)
C11	0.16431 (15)	−0.0971 (5)	0.09304 (15)	0.0177 (5)	0.503 (2)
H11A	0.2047	−0.2365	0.0871	0.021*	0.503 (2)
C12	0.09495 (15)	−0.1604 (5)	0.13298 (15)	0.0176 (5)	0.503 (2)
H12A	0.0897	−0.3359	0.1569	0.021*	0.503 (2)
C14	0.04106 (15)	0.2993 (5)	0.10535 (15)	0.0187 (5)	0.503 (2)
H14A	−0.0012	0.4336	0.1098	0.022*	0.503 (2)
C15	0.11108 (15)	0.3605 (5)	0.06696 (15)	0.0181 (5)	0.503 (2)
H15A	0.1161	0.5370	0.0436	0.022*	0.503 (2)
C11X	0.18437 (14)	0.0503 (5)	0.14160 (14)	0.0155 (5)	0.497 (2)
H11B	0.2384	0.0184	0.1695	0.019*	0.497 (2)
C12X	0.11256 (15)	−0.0091 (5)	0.17791 (14)	0.0159 (5)	0.497 (2)
H12B	0.1174	−0.0822	0.2307	0.019*	0.497 (2)
C14X	0.02656 (14)	0.1474 (5)	0.05831 (14)	0.0169 (5)	0.497 (2)
H14B	−0.0273	0.1799	0.0301	0.020*	0.497 (2)
C15X	0.09871 (15)	0.2059 (5)	0.02300 (14)	0.0173 (5)	0.497 (2)
H15B	0.0937	0.2799	−0.0297	0.021*	0.497 (2)
C16	0.36592 (8)	−0.1175 (4)	0.07881 (8)	0.0274 (3)
H16A	0.3312	−0.1937	0.1154	0.033*

	U11	U22	U33	U12	U13	U23
Cl1	0.01577 (14)	0.02598 (17)	0.02634 (17)	−0.00049 (11)	0.00943 (11)	0.00063 (13)
O1	0.0174 (4)	0.0356 (6)	0.0282 (5)	0.0042 (4)	0.0033 (4)	0.0034 (4)
N1	0.0180 (5)	0.0166 (5)	0.0209 (5)	−0.0017 (4)	0.0091 (4)	−0.0018 (4)
N2	0.0182 (5)	0.0174 (5)	0.0232 (5)	−0.0007 (4)	0.0105 (4)	−0.0014 (4)
C1	0.0240 (6)	0.0170 (6)	0.0336 (7)	0.0012 (5)	0.0140 (5)	0.0014 (5)
C2	0.0267 (6)	0.0191 (6)	0.0316 (7)	−0.0023 (5)	0.0161 (5)	−0.0004 (6)
C3	0.0300 (7)	0.0229 (7)	0.0197 (6)	−0.0059 (6)	0.0082 (5)	0.0001 (5)
C4	0.0233 (6)	0.0360 (8)	0.0232 (6)	−0.0034 (6)	0.0016 (5)	0.0054 (6)
C5	0.0194 (6)	0.0331 (8)	0.0215 (6)	−0.0046 (5)	0.0041 (5)	0.0029 (6)
C6	0.0223 (6)	0.0149 (6)	0.0193 (6)	−0.0035 (5)	0.0089 (4)	−0.0032 (5)
C7	0.0170 (5)	0.0178 (6)	0.0205 (6)	−0.0017 (5)	0.0061 (4)	−0.0035 (5)
C8	0.0149 (5)	0.0190 (6)	0.0182 (5)	−0.0022 (4)	0.0048 (4)	−0.0039 (5)
C9	0.0164 (5)	0.0165 (6)	0.0180 (5)	−0.0024 (4)	0.0054 (4)	−0.0041 (5)
C10	0.0155 (5)	0.0162 (6)	0.0171 (5)	−0.0009 (4)	0.0053 (4)	−0.0024 (4)
C13	0.0136 (5)	0.0179 (6)	0.0166 (5)	−0.0007 (4)	0.0046 (4)	−0.0015 (4)
C11	0.0130 (10)	0.0192 (12)	0.0209 (12)	0.0028 (9)	0.0021 (8)	0.0000 (9)
C12	0.0169 (10)	0.0169 (12)	0.0192 (11)	−0.0001 (9)	0.0030 (8)	0.0023 (9)
C14	0.0164 (10)	0.0198 (12)	0.0205 (12)	0.0042 (9)	0.0049 (9)	−0.0010 (10)
C15	0.0189 (11)	0.0156 (11)	0.0207 (11)	0.0008 (9)	0.0059 (9)	−0.0002 (10)
C11X	0.0127 (10)	0.0170 (11)	0.0166 (11)	0.0012 (9)	0.0013 (8)	−0.0008 (9)
C12X	0.0161 (10)	0.0176 (12)	0.0145 (10)	0.0003 (9)	0.0037 (8)	0.0018 (9)
C14X	0.0127 (10)	0.0201 (12)	0.0176 (11)	0.0003 (9)	0.0005 (8)	−0.0011 (10)
C15X	0.0170 (11)	0.0197 (12)	0.0152 (11)	−0.0001 (9)	0.0020 (8)	0.0017 (9)
C16	0.0160 (6)	0.0436 (9)	0.0232 (6)	0.0018 (6)	0.0047 (5)	0.0092 (6)

Cl1—C13	1.7405 (12)	C10—C15X	1.355 (3)
O1—C16	1.2168 (16)	C10—C11	1.371 (3)
N1—C7	1.3427 (17)	C10—C11X	1.427 (3)
N1—N2	1.3749 (13)	C10—C15	1.437 (3)
N1—C6	1.4287 (16)	C13—C14	1.379 (3)
N2—C9	1.3301 (16)	C13—C12	1.379 (3)
C1—C6	1.3909 (17)	C13—C12X	1.381 (3)
C1—C2	1.3935 (19)	C13—C14X	1.411 (3)
C1—H1A	0.9500	C11—C12	1.398 (3)
C2—C3	1.383 (2)	C11—H11A	0.9500
C2—H2A	0.9500	C12—H12A	0.9500
C3—C4	1.3908 (18)	C14—C15	1.390 (3)
C3—H3A	0.9500	C14—H14A	0.9500
C4—C5	1.391 (2)	C15—H15A	0.9500
C4—H4A	0.9500	C11X—C12X	1.394 (3)
C5—C6	1.3844 (19)	C11X—H11B	0.9500
C5—H5A	0.9500	C12X—H12B	0.9500
C7—C8	1.3877 (17)	C14X—C15X	1.389 (3)
C7—H7A	0.9500	C14X—H14B	0.9500
C8—C9	1.4292 (16)	C15X—H15B	0.9500
C8—C16	1.441 (2)	C16—H16A	0.9500
C9—C10	1.4795 (16)
C7—N1—N2	112.33 (10)	C15—C10—C9	120.41 (14)
C7—N1—C6	128.90 (10)	C14—C13—C12	122.76 (16)
N2—N1—C6	118.77 (10)	C14—C13—C12X	103.95 (17)
C9—N2—N1	104.97 (10)	C12—C13—C12X	45.55 (15)
C6—C1—C2	118.74 (13)	C14—C13—C14X	45.84 (15)
C6—C1—H1A	120.6	C12—C13—C14X	101.97 (16)
C2—C1—H1A	120.6	C12X—C13—C14X	120.63 (16)
C3—C2—C1	120.88 (12)	C14—C13—Cl1	118.80 (13)
C3—C2—H2A	119.6	C12—C13—Cl1	118.43 (13)
C1—C2—H2A	119.6	C12X—C13—Cl1	119.40 (13)
C2—C3—C4	119.58 (13)	C14X—C13—Cl1	119.94 (12)
C2—C3—H3A	120.2	C10—C11—C12	122.2 (2)
C4—C3—H3A	120.2	C10—C11—H11A	118.9
C3—C4—C5	120.33 (13)	C12—C11—H11A	118.9
C3—C4—H4A	119.8	C13—C12—C11	118.1 (2)
C5—C4—H4A	119.8	C13—C12—H12A	120.9
C6—C5—C4	119.36 (12)	C11—C12—H12A	120.9
C6—C5—H5A	120.3	C13—C14—C15	118.4 (2)
C4—C5—H5A	120.3	C13—C14—H14A	120.8
C5—C6—C1	121.10 (12)	C15—C14—H14A	120.8
C5—C6—N1	118.87 (11)	C14—C15—C10	120.7 (2)
C1—C6—N1	120.02 (12)	C14—C15—H15A	119.7
N1—C7—C8	107.12 (11)	C10—C15—H15A	119.7
N1—C7—H7A	126.4	C12X—C11X—C10	119.5 (2)
C8—C7—H7A	126.4	C12X—C11X—H11B	120.3
C7—C8—C9	104.61 (11)	C10—C11X—H11B	120.3
C7—C8—C16	125.38 (11)	C13—C12X—C11X	119.6 (2)
C9—C8—C16	129.99 (11)	C13—C12X—H12B	120.2
N2—C9—C8	110.96 (10)	C11X—C12X—H12B	120.2
N2—C9—C10	118.70 (11)	C15X—C14X—C13	119.0 (2)
C8—C9—C10	130.32 (11)	C15X—C14X—H14B	120.5
C15X—C10—C11	100.24 (17)	C13—C14X—H14B	120.5
C15X—C10—C11X	119.92 (16)	C10—C15X—C14X	121.3 (2)
C11—C10—C11X	46.48 (15)	C10—C15X—H15B	119.3
C11—C10—C15	117.75 (16)	C14X—C15X—H15B	119.3
C11X—C10—C15	101.05 (15)	O1—C16—C8	125.03 (13)
C15X—C10—C9	118.24 (14)	O1—C16—H16A	117.5
C11—C10—C9	121.72 (14)	C8—C16—H16A	117.5
C11X—C10—C9	121.83 (13)
C7—N1—N2—C9	0.05 (14)	C9—C10—C11—C12	179.58 (18)
C6—N1—N2—C9	179.65 (11)	C14—C13—C12—C11	−2.3 (3)
C6—C1—C2—C3	0.3 (2)	C12X—C13—C12—C11	−79.1 (3)
C1—C2—C3—C4	0.2 (2)	C14X—C13—C12—C11	42.4 (3)
C2—C3—C4—C5	−0.6 (2)	Cl1—C13—C12—C11	176.41 (17)
C3—C4—C5—C6	0.5 (2)	C10—C11—C12—C13	4.0 (3)
C4—C5—C6—C1	0.1 (2)	C12—C13—C14—C15	1.3 (3)
C4—C5—C6—N1	179.29 (13)	C12X—C13—C14—C15	47.0 (3)
C2—C1—C6—C5	−0.5 (2)	C14X—C13—C14—C15	−72.4 (2)
C2—C1—C6—N1	−179.69 (12)	Cl1—C13—C14—C15	−177.43 (17)
C7—N1—C6—C5	172.00 (13)	C13—C14—C15—C10	−1.7 (3)
N2—N1—C6—C5	−7.51 (17)	C15X—C10—C15—C14	78.7 (3)
C7—N1—C6—C1	−8.8 (2)	C11—C10—C15—C14	3.2 (3)
N2—N1—C6—C1	171.72 (12)	C11X—C10—C15—C14	−43.1 (3)
N2—N1—C7—C8	−0.27 (14)	C9—C10—C15—C14	179.34 (18)
C6—N1—C7—C8	−179.81 (12)	C15X—C10—C11X—C12X	0.4 (3)
N1—C7—C8—C9	0.36 (13)	C11—C10—C11X—C12X	−74.3 (3)
N1—C7—C8—C16	178.86 (13)	C15—C10—C11X—C12X	43.6 (3)
N1—N2—C9—C8	0.19 (13)	C9—C10—C11X—C12X	−179.63 (18)
N1—N2—C9—C10	−178.74 (10)	C14—C13—C12X—C11X	−46.5 (3)
C7—C8—C9—N2	−0.34 (14)	C12—C13—C12X—C11X	76.0 (3)
C16—C8—C9—N2	−178.75 (14)	C14X—C13—C12X—C11X	0.1 (3)
C7—C8—C9—C10	178.42 (12)	Cl1—C13—C12X—C11X	178.26 (17)
C16—C8—C9—C10	0.0 (2)	C10—C11X—C12X—C13	−0.2 (3)
N2—C9—C10—C15X	28.1 (2)	C14—C13—C14X—C15X	79.2 (3)
C8—C9—C10—C15X	−150.62 (17)	C12—C13—C14X—C15X	−45.2 (3)
N2—C9—C10—C11	152.77 (16)	C12X—C13—C14X—C15X	−0.2 (3)
C8—C9—C10—C11	−25.9 (2)	Cl1—C13—C14X—C15X	−178.35 (18)
N2—C9—C10—C11X	−151.92 (16)	C11—C10—C15X—C14X	44.8 (3)
C8—C9—C10—C11X	29.4 (2)	C11X—C10—C15X—C14X	−0.5 (3)
N2—C9—C10—C15	−23.2 (2)	C15—C10—C15X—C14X	−74.7 (3)
C8—C9—C10—C15	158.14 (16)	C9—C10—C15X—C14X	179.5 (2)
C15X—C10—C11—C12	−47.8 (3)	C13—C14X—C15X—C10	0.4 (4)
C11X—C10—C11—C12	74.0 (3)	C7—C8—C16—O1	−1.5 (2)
C15—C10—C11—C12	−4.4 (3)	C9—C8—C16—O1	176.61 (14)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1A···O1i	0.95	2.42	3.3545 (18)	167
C7—H7A···O1i	0.95	2.33	3.2684 (16)	169

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1A⋯O1i	0.95	2.42	3.3545 (18)	167
C7—H7A⋯O1i	0.95	2.33	3.2684 (16)	169

Symmetry code: (i) .