5-(4-Chloro-phen-oxy)-3-methyl-1-phenyl-1H-pyrazole-4-carbaldehyde.

In the title compound, C17H13ClN2O2, the phenyl and chloro-benzene rings are inclined to the central pyrazole ring at 40.84 (9) and 65.30 (9)°, respectively. In the crystal, pairs of C-H⋯π inter-actions link the mol-ecules into inversion dimers and C-H⋯O hydrogen bonds link these dimers into columns extended in [010]. The crystal packing exhibits short inter-molecular O⋯Cl contacts of 3.0913 (16) Å.

Related literature

For biological properties and pharmocological applications of ar­yloxy pyrazole derivatives, see: Rai et al. (2008 ▶); Girisha et al. (2010 ▶); Isloor et al. (2009 ▶, 2010 ▶); Shobhitha et al. (2013 ▶). For related structures, see: Shahani, Fun, Ragavan et al. (2011 ▶); Shahani, Fun, Shetty et al. (2011 ▶); Prasath et al. (2011 ▶).

Experimental

Crystal data

C17H13ClN2O2

M = 312.74

Monoclinic,

a = 9.1016 (7) Å

b = 7.5298 (6) Å

c = 22.1242 (16) Å

β = 93.908 (3)°

V = 1512.7 (2) Å3

Z = 4

Cu Kα radiation

μ = 2.31 mm−1

T = 296 K

0.23 × 0.22 × 0.21 mm

Data collection

Bruker X8 Proteum diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2013 ▶) T min = 0.619, T max = 0.643

9744 measured reflections

2501 independent reflections

2314 reflections with I > 2σ(I)

R int = 0.041

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.105

S = 1.03

2501 reflections

200 parameters

H-atom parameters constrained

Δρmax = 0.25 e Å−3

Δρmin = −0.38 e Å−3

Data collection: APEX2 (Bruker, 2013 ▶); cell refinement: SAINT (Bruker, 2013 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536814007879/cv5447sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814007879/cv5447Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814007879/cv5447Isup3.cml

CCDC reference: 996262

Additional supporting information: crystallographic information; 3D view; checkCIF report

C17H13ClN2O2	F(000) = 648
Mr = 312.74	Dx = 1.373 Mg m−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: -P 2ybc	Cell parameters from 2501 reflections
a = 9.1016 (7) Å	θ = 4.0–64.4°
b = 7.5298 (6) Å	µ = 2.31 mm−1
c = 22.1242 (16) Å	T = 296 K
β = 93.908 (3)°	Block, brown
V = 1512.7 (2) Å3	0.23 × 0.22 × 0.21 mm
Z = 4

Bruker X8 Proteum diffractometer	2501 independent reflections
Radiation source: Bruker MicroStar microfocus rotating anode	2314 reflections with I > 2σ(I)
Helios multilayer optics monochromator	Rint = 0.041
Detector resolution: 18.4 pixels mm-1	θmax = 64.5°, θmin = 4.0°
φ and ω scans	h = −10→10
Absorption correction: multi-scan (SADABS; Bruker, 2013)	k = −3→8
Tmin = 0.619, Tmax = 0.643	l = −25→25
9744 measured reflections

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)] = 0.039	H-atom parameters constrained
wR(F2) = 0.105	w = 1/[σ2(Fo2) + (0.0555P)2 + 0.5076P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max < 0.001
2501 reflections	Δρmax = 0.25 e Å−3
200 parameters	Δρmin = −0.38 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), FC*=KFC[1+0.001XFC2Λ3/SIN(2Θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0171 (10)

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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	0.33674 (5)	0.67384 (7)	0.29951 (2)	0.0525 (2)
O1	0.96938 (13)	0.67414 (15)	0.37256 (6)	0.0417 (4)
O2	0.96678 (16)	0.16557 (19)	0.27222 (7)	0.0579 (5)
N1	1.15356 (14)	0.51714 (19)	0.42604 (6)	0.0354 (4)
N2	1.23196 (16)	0.3599 (2)	0.42482 (7)	0.0420 (5)
C1	0.81860 (18)	0.6650 (2)	0.35492 (7)	0.0335 (5)
C2	0.72891 (19)	0.5340 (3)	0.37544 (8)	0.0419 (5)
C3	0.58011 (19)	0.5360 (3)	0.35785 (8)	0.0417 (5)
C4	0.52407 (19)	0.6712 (2)	0.32108 (7)	0.0378 (5)
C5	0.6139 (2)	0.8024 (2)	0.30129 (8)	0.0438 (6)
C6	0.7637 (2)	0.8000 (2)	0.31799 (8)	0.0403 (6)
C7	1.04684 (16)	0.5223 (2)	0.38079 (7)	0.0332 (5)
C8	1.05021 (18)	0.3640 (2)	0.34914 (7)	0.0354 (5)
C9	1.16849 (19)	0.2680 (2)	0.37941 (8)	0.0398 (5)
C10	0.9588 (2)	0.3101 (3)	0.29611 (8)	0.0407 (6)
C11	1.20153 (18)	0.6520 (2)	0.46814 (7)	0.0336 (5)
C12	1.3510 (2)	0.6767 (2)	0.47974 (8)	0.0407 (6)
C13	1.4008 (2)	0.8051 (3)	0.52092 (9)	0.0488 (6)
C14	1.3028 (2)	0.9086 (3)	0.54945 (9)	0.0533 (7)
C15	1.1529 (2)	0.8822 (3)	0.53819 (8)	0.0495 (6)
C16	1.10095 (19)	0.7530 (2)	0.49751 (7)	0.0404 (5)
C17	1.2243 (2)	0.0881 (3)	0.36473 (11)	0.0592 (7)
H02A	1.30480	0.05740	0.39310	0.0890*
H2	0.76800	0.44510	0.40090	0.0500*
H02B	1.25740	0.08840	0.32440	0.0890*
H3	0.51850	0.44700	0.37070	0.0500*
H02C	1.14670	0.00270	0.36720	0.0890*
H5	0.57430	0.89290	0.27670	0.0530*
H6	0.82560	0.88770	0.30450	0.0480*
H10	0.89020	0.39080	0.27940	0.0490*
H12	1.41770	0.60760	0.46010	0.0490*
H13	1.50150	0.82140	0.52930	0.0590*
H14	1.33690	0.99660	0.57640	0.0640*
H15	1.08660	0.95150	0.55800	0.0590*
H16	1.00030	0.73440	0.49010	0.0480*

	U11	U22	U33	U12	U13	U23
Cl1	0.0314 (3)	0.0597 (4)	0.0649 (3)	0.0089 (2)	−0.0083 (2)	−0.0045 (2)
O1	0.0335 (6)	0.0355 (7)	0.0536 (7)	0.0015 (5)	−0.0141 (5)	0.0023 (5)
O2	0.0543 (9)	0.0558 (9)	0.0619 (9)	−0.0033 (6)	−0.0090 (7)	−0.0195 (7)
N1	0.0304 (7)	0.0367 (8)	0.0378 (7)	0.0046 (6)	−0.0069 (5)	−0.0024 (6)
N2	0.0365 (8)	0.0382 (8)	0.0497 (8)	0.0084 (6)	−0.0094 (6)	−0.0035 (6)
C1	0.0294 (8)	0.0379 (9)	0.0321 (8)	0.0039 (6)	−0.0057 (6)	−0.0005 (6)
C2	0.0382 (9)	0.0447 (10)	0.0418 (9)	0.0044 (8)	−0.0038 (7)	0.0129 (7)
C3	0.0342 (9)	0.0454 (10)	0.0456 (9)	0.0018 (7)	0.0038 (7)	0.0068 (8)
C4	0.0316 (9)	0.0442 (10)	0.0368 (8)	0.0072 (7)	−0.0034 (7)	−0.0030 (7)
C5	0.0423 (10)	0.0432 (10)	0.0445 (9)	0.0091 (8)	−0.0071 (8)	0.0099 (8)
C6	0.0390 (10)	0.0379 (10)	0.0435 (9)	0.0020 (7)	−0.0014 (7)	0.0076 (7)
C7	0.0258 (7)	0.0365 (9)	0.0364 (8)	0.0000 (6)	−0.0044 (6)	0.0037 (7)
C8	0.0302 (8)	0.0366 (9)	0.0386 (8)	−0.0034 (7)	−0.0030 (6)	0.0003 (7)
C9	0.0340 (9)	0.0393 (10)	0.0453 (9)	0.0013 (7)	−0.0021 (7)	−0.0040 (7)
C10	0.0360 (9)	0.0442 (11)	0.0409 (9)	−0.0062 (7)	−0.0037 (7)	−0.0020 (8)
C11	0.0350 (9)	0.0340 (9)	0.0308 (8)	0.0012 (6)	−0.0042 (6)	0.0031 (6)
C12	0.0340 (9)	0.0490 (11)	0.0386 (9)	0.0006 (7)	−0.0020 (7)	−0.0009 (7)
C13	0.0440 (10)	0.0539 (12)	0.0468 (10)	−0.0090 (9)	−0.0097 (8)	−0.0019 (8)
C14	0.0658 (13)	0.0454 (12)	0.0467 (10)	−0.0040 (9)	−0.0104 (9)	−0.0069 (8)
C15	0.0623 (12)	0.0430 (11)	0.0429 (9)	0.0136 (9)	0.0021 (8)	−0.0035 (8)
C16	0.0360 (9)	0.0432 (10)	0.0412 (9)	0.0062 (7)	−0.0023 (7)	0.0021 (8)
C17	0.0530 (12)	0.0482 (12)	0.0741 (13)	0.0116 (10)	−0.0122 (10)	−0.0135 (10)

Cl1—C4	1.7390 (18)	C11—C16	1.386 (2)
O1—C1	1.403 (2)	C12—C13	1.384 (3)
O1—C7	1.3490 (19)	C13—C14	1.370 (3)
O2—C10	1.214 (3)	C14—C15	1.384 (3)
N1—N2	1.384 (2)	C15—C16	1.386 (3)
N1—C7	1.347 (2)	C2—H2	0.9300
N1—C11	1.426 (2)	C3—H3	0.9300
N2—C9	1.320 (2)	C5—H5	0.9300
C1—C2	1.377 (3)	C6—H6	0.9300
C1—C6	1.377 (2)	C10—H10	0.9300
C2—C3	1.384 (2)	C12—H12	0.9300
C3—C4	1.379 (3)	C13—H13	0.9300
C4—C5	1.373 (2)	C14—H14	0.9300
C5—C6	1.388 (3)	C15—H15	0.9300
C7—C8	1.384 (2)	C16—H16	0.9300
C8—C9	1.425 (2)	C17—H02A	0.9600
C8—C10	1.449 (2)	C17—H02B	0.9600
C9—C17	1.490 (3)	C17—H02C	0.9600
C11—C12	1.380 (2)
C1—O1—C7	119.23 (12)	C13—C14—C15	119.99 (19)
N2—N1—C7	110.91 (13)	C14—C15—C16	120.39 (18)
N2—N1—C11	119.12 (13)	C11—C16—C15	118.86 (16)
C7—N1—C11	129.64 (14)	C1—C2—H2	120.00
N1—N2—C9	105.30 (13)	C3—C2—H2	120.00
O1—C1—C2	122.29 (14)	C2—C3—H3	120.00
O1—C1—C6	115.95 (14)	C4—C3—H3	120.00
C2—C1—C6	121.69 (16)	C4—C5—H5	120.00
C1—C2—C3	119.37 (18)	C6—C5—H5	120.00
C2—C3—C4	119.31 (18)	C1—C6—H6	121.00
Cl1—C4—C3	119.12 (13)	C5—C6—H6	121.00
Cl1—C4—C5	119.89 (13)	O2—C10—H10	118.00
C3—C4—C5	121.00 (16)	C8—C10—H10	118.00
C4—C5—C6	120.08 (15)	C11—C12—H12	120.00
C1—C6—C5	118.54 (15)	C13—C12—H12	120.00
O1—C7—N1	117.94 (14)	C12—C13—H13	120.00
O1—C7—C8	133.72 (14)	C14—C13—H13	120.00
N1—C7—C8	108.15 (13)	C13—C14—H14	120.00
C7—C8—C9	103.96 (14)	C15—C14—H14	120.00
C7—C8—C10	128.28 (16)	C14—C15—H15	120.00
C9—C8—C10	127.72 (15)	C16—C15—H15	120.00
N2—C9—C8	111.66 (14)	C11—C16—H16	121.00
N2—C9—C17	120.29 (16)	C15—C16—H16	121.00
C8—C9—C17	128.05 (16)	C9—C17—H02A	109.00
O2—C10—C8	123.73 (18)	C9—C17—H02B	109.00
N1—C11—C12	118.14 (14)	C9—C17—H02C	109.00
N1—C11—C16	120.96 (14)	H02A—C17—H02B	110.00
C12—C11—C16	120.89 (15)	H02A—C17—H02C	109.00
C11—C12—C13	119.43 (16)	H02B—C17—H02C	109.00
C12—C13—C14	120.43 (17)
C7—O1—C1—C2	36.1 (2)	C2—C3—C4—C5	0.6 (3)
C7—O1—C1—C6	−146.92 (15)	Cl1—C4—C5—C6	−179.47 (13)
C1—O1—C7—N1	−143.39 (14)	C3—C4—C5—C6	0.3 (3)
C1—O1—C7—C8	42.4 (2)	C4—C5—C6—C1	−0.6 (2)
C7—N1—N2—C9	−1.81 (18)	O1—C7—C8—C9	174.01 (17)
C11—N1—N2—C9	−175.88 (14)	O1—C7—C8—C10	−3.9 (3)
N2—N1—C7—O1	−174.08 (13)	N1—C7—C8—C9	−0.60 (17)
N2—N1—C7—C8	1.51 (18)	N1—C7—C8—C10	−178.50 (16)
C11—N1—C7—O1	−0.8 (2)	C7—C8—C9—N2	−0.55 (19)
C11—N1—C7—C8	174.78 (15)	C7—C8—C9—C17	−179.41 (17)
N2—N1—C11—C12	37.2 (2)	C10—C8—C9—N2	177.37 (17)
N2—N1—C11—C16	−141.54 (15)	C10—C8—C9—C17	−1.5 (3)
C7—N1—C11—C12	−135.63 (17)	C7—C8—C10—O2	−177.79 (18)
C7—N1—C11—C16	45.7 (2)	C9—C8—C10—O2	4.8 (3)
N1—N2—C9—C8	1.42 (19)	N1—C11—C12—C13	−179.23 (16)
N1—N2—C9—C17	−179.62 (16)	C16—C11—C12—C13	−0.5 (2)
O1—C1—C2—C3	177.88 (16)	N1—C11—C16—C15	179.80 (15)
C6—C1—C2—C3	1.0 (3)	C12—C11—C16—C15	1.1 (2)
O1—C1—C6—C5	−177.13 (15)	C11—C12—C13—C14	−0.8 (3)
C2—C1—C6—C5	−0.1 (3)	C12—C13—C14—C15	1.5 (3)
C1—C2—C3—C4	−1.3 (3)	C13—C14—C15—C16	−0.9 (3)
C2—C3—C4—Cl1	−179.59 (14)	C14—C15—C16—C11	−0.4 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O2i	0.93	2.58	3.503 (2)	171
C2—H2···Cgii	0.93	2.63	3.476 (2)	152

Table 1

Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C11–C16 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯O2i	0.93	2.58	3.503 (2)	171
C2—H2⋯Cg ii	0.93	2.63	3.476 (2)	152

Symmetry codes: (i) ; (ii) .