Crystal structure of [1-(3-chloro-phen-yl)-5-hy-droxy-3-methyl-1H-pyrazol-4-yl](p-tol-yl)methanone.

In the title compound C18H15ClN2O2, the dihedral angles between the central pyrazole ring and the pendant chloro-benzene and p-tolyl rings are 17.68 (10) and 51.26 (12)°, respectively. An intra-molecular O-H⋯O hydrogen bond is observed, which closes an S(6) ring.

Related literature

For background to 4-acyl­pyrazolone derivatives, see: Jadeja et al. (2012 ▸); Chiba et al. (1998 ▸); Marchetti et al. (2005 ▸). For related structures, see: Sharma et al. (2014 ▸); Abdel-Aziz et al. (2012 ▸).

Experimental

Crystal data

C18H15ClN2O2

M = 326.77

Triclinic,

a = 5.1469 (5) Å

b = 12.0773 (12) Å

c = 13.0892 (11) Å

α = 87.247 (7)°

β = 84.396 (7)°

γ = 79.024 (9)°

V = 794.57 (13) Å3

Z = 2

Mo Kα radiation

μ = 0.25 mm−1

T = 293 K

0.30 × 0.20 × 0.20 mm

Data collection

Oxford Diffraction Xcalibur, Sapphire3 diffractometer

Absorption correction: multi-scan (SCALE3 ABSPACK in CrysAlis PRO; Oxford Diffraction, 2010 ▸) T min = 0.745, T max = 1.000

5633 measured reflections

3099 independent reflections

1411 reflections with I > 2σ(I)

R int = 0.041

Refinement

R[F 2 > 2σ(F 2)] = 0.062

wR(F 2) = 0.164

S = 1.00

3099 reflections

210 parameters

H-atom parameters constrained

Δρmax = 0.17 e Å−3

Δρmin = −0.20 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 ▸); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▸); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▸); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▸); software used to prepare material for publication: PLATON (Spek, 2009 ▸).

Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S2056989015006258/hb7373sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015006258/hb7373Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S2056989015006258/hb7373Isup3.cml

Click here for additional data file.

ORTEP . DOI: 10.1107/S2056989015006258/hb7373fig1.tif

ORTEP view of the title mol­ecule with displacement ellipsoids drawn at the 40% probability level.

Click here for additional data file.

a . DOI: 10.1107/S2056989015006258/hb7373fig2.tif

The packing arrangement of mol­ecules viewed down the a axis.

CCDC reference: 1056475

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

C18H15ClN2O2	Z = 2
Mr = 326.77	F(000) = 340
Triclinic, P1	Dx = 1.366 Mg m−3Dm = 1.37 Mg m−3Dm measured by not measured
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.1469 (5) Å	Cell parameters from 1318 reflections
b = 12.0773 (12) Å	θ = 4.1–26.7°
c = 13.0892 (11) Å	µ = 0.25 mm−1
α = 87.247 (7)°	T = 293 K
β = 84.396 (7)°	Block, yellow
γ = 79.024 (9)°	0.30 × 0.20 × 0.20 mm
V = 794.57 (13) Å3

Oxford Diffraction Xcalibur, Sapphire3 diffractometer	3099 independent reflections
Radiation source: fine-focus sealed tube	1411 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.041
Detector resolution: 16.1049 pixels mm-1	θmax = 26.0°, θmin = 3.4°
ω Scan scans	h = −6→6
Absorption correction: multi-scan (SCALE3 ABSPACK in CrysAlis PRO; Oxford Diffraction, 2010)	k = −14→12
Tmin = 0.745, Tmax = 1.000	l = −16→15
5633 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)] = 0.062	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.164	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.0513P)2] where P = (Fo2 + 2Fc2)/3
3099 reflections	(Δ/σ)max < 0.001
210 parameters	Δρmax = 0.17 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	0.3593 (2)	0.51342 (10)	0.37363 (9)	0.1138 (5)
O14	0.9153 (4)	0.0200 (2)	−0.12991 (19)	0.0789 (8)
N2	0.6078 (5)	0.2834 (2)	0.0517 (2)	0.0628 (8)
O3	0.5663 (4)	0.10070 (19)	0.01592 (18)	0.0789 (8)
H3	0.6322	0.0518	−0.0252	0.118*
N1	0.7645 (5)	0.3616 (2)	0.0144 (2)	0.0660 (8)
C7	0.4381 (6)	0.3048 (3)	0.1427 (3)	0.0612 (9)
C14	0.9791 (6)	0.1164 (3)	−0.1490 (3)	0.0661 (10)
C8	0.4715 (6)	0.3904 (3)	0.2042 (3)	0.0671 (10)
H8	0.5998	0.4340	0.1850	0.080*
C15	1.1641 (6)	0.1285 (3)	−0.2406 (3)	0.0584 (9)
C4	0.8677 (6)	0.2055 (3)	−0.0821 (3)	0.0596 (9)
C5	0.9158 (6)	0.3162 (3)	−0.0646 (3)	0.0591 (9)
C18	1.5098 (7)	0.1494 (4)	−0.4158 (3)	0.0759 (11)
C16	1.3803 (7)	0.0454 (3)	−0.2639 (3)	0.0721 (10)
H16	1.4115	−0.0190	−0.2217	0.087*
C9	0.3107 (7)	0.4095 (3)	0.2944 (3)	0.0751 (11)
C11	0.0854 (7)	0.2626 (4)	0.2618 (3)	0.0858 (12)
H11	−0.0425	0.2188	0.2814	0.103*
C20	1.1174 (7)	0.2212 (3)	−0.3063 (3)	0.0737 (10)
H20	0.9691	0.2774	−0.2921	0.088*
C3	0.6724 (6)	0.1890 (3)	−0.0040 (3)	0.0626 (9)
C12	0.2420 (6)	0.2418 (3)	0.1708 (3)	0.0733 (11)
H12	0.2166	0.1859	0.1284	0.088*
C6	1.1176 (6)	0.3801 (3)	−0.1179 (3)	0.0733 (11)
H6A	1.0483	0.4191	−0.1780	0.110*
H6B	1.2784	0.3282	−0.1377	0.110*
H6C	1.1544	0.4338	−0.0721	0.110*
C10	0.1147 (7)	0.3465 (4)	0.3240 (3)	0.0851 (13)
H10	0.0058	0.3612	0.3847	0.102*
C17	1.5527 (7)	0.0571 (4)	−0.3503 (3)	0.0835 (12)
H17	1.7012	0.0009	−0.3641	0.100*
C19	1.2894 (8)	0.2317 (4)	−0.3935 (3)	0.0827 (12)
H19	1.2552	0.2949	−0.4370	0.099*
C21	1.6955 (8)	0.1619 (4)	−0.5112 (3)	0.1139 (16)
H21A	1.6488	0.1217	−0.5661	0.171*
H21B	1.8752	0.1316	−0.4970	0.171*
H21C	1.6802	0.2404	−0.5308	0.171*

	U11	U22	U33	U12	U13	U23
Cl1	0.1352 (10)	0.1143 (10)	0.0849 (9)	−0.0078 (7)	0.0057 (7)	−0.0276 (8)
O14	0.0959 (17)	0.0706 (17)	0.0744 (18)	−0.0365 (14)	0.0131 (13)	−0.0027 (14)
N2	0.0660 (17)	0.0642 (19)	0.0591 (19)	−0.0223 (14)	0.0078 (14)	0.0016 (16)
O3	0.0893 (16)	0.0740 (17)	0.0770 (19)	−0.0360 (14)	0.0159 (14)	−0.0026 (15)
N1	0.0724 (17)	0.064 (2)	0.063 (2)	−0.0256 (15)	0.0060 (15)	0.0046 (15)
C7	0.0538 (19)	0.071 (2)	0.053 (2)	−0.0069 (17)	0.0046 (16)	0.0139 (18)
C14	0.068 (2)	0.079 (3)	0.054 (2)	−0.0241 (19)	−0.0048 (17)	0.008 (2)
C8	0.070 (2)	0.065 (2)	0.062 (2)	−0.0086 (18)	0.0025 (18)	0.0011 (19)
C15	0.069 (2)	0.061 (2)	0.049 (2)	−0.0225 (17)	−0.0024 (17)	−0.0053 (18)
C4	0.0609 (19)	0.065 (2)	0.056 (2)	−0.0222 (17)	0.0037 (16)	−0.0032 (18)
C5	0.065 (2)	0.063 (2)	0.050 (2)	−0.0180 (17)	0.0011 (16)	0.0082 (17)
C18	0.078 (2)	0.103 (3)	0.056 (3)	−0.041 (2)	0.000 (2)	−0.008 (2)
C16	0.083 (2)	0.070 (3)	0.061 (3)	−0.015 (2)	0.0024 (19)	0.006 (2)
C9	0.085 (2)	0.080 (3)	0.050 (2)	0.007 (2)	−0.0008 (19)	0.002 (2)
C11	0.071 (2)	0.104 (3)	0.078 (3)	−0.017 (2)	0.014 (2)	0.008 (3)
C20	0.089 (2)	0.075 (3)	0.056 (3)	−0.014 (2)	−0.0051 (19)	0.006 (2)
C3	0.064 (2)	0.070 (2)	0.058 (2)	−0.0267 (18)	0.0003 (17)	0.0068 (19)
C12	0.062 (2)	0.084 (3)	0.072 (3)	−0.0156 (19)	0.0028 (19)	0.007 (2)
C6	0.086 (2)	0.072 (3)	0.065 (2)	−0.0315 (19)	0.0070 (19)	0.007 (2)
C10	0.078 (3)	0.100 (3)	0.064 (3)	0.002 (2)	0.016 (2)	0.018 (2)
C17	0.078 (2)	0.095 (3)	0.073 (3)	−0.011 (2)	0.006 (2)	−0.007 (3)
C19	0.106 (3)	0.088 (3)	0.059 (3)	−0.035 (2)	−0.006 (2)	0.012 (2)
C21	0.112 (3)	0.170 (5)	0.071 (3)	−0.069 (3)	0.024 (2)	−0.011 (3)

Cl1—C9	1.735 (4)	C18—C19	1.376 (5)
O14—C14	1.276 (4)	C18—C21	1.516 (5)
N2—C3	1.352 (4)	C16—C17	1.386 (4)
N2—N1	1.397 (3)	C16—H16	0.9300
N2—C7	1.410 (4)	C9—C10	1.390 (5)
O3—C3	1.293 (3)	C11—C10	1.369 (5)
O3—H3	0.8200	C11—C12	1.377 (4)
N1—C5	1.307 (4)	C11—H11	0.9300
C7—C8	1.386 (4)	C20—C19	1.391 (4)
C7—C12	1.388 (4)	C20—H20	0.9300
C14—C4	1.418 (4)	C12—H12	0.9300
C14—C15	1.477 (4)	C6—H6A	0.9600
C8—C9	1.376 (4)	C6—H6B	0.9600
C8—H8	0.9300	C6—H6C	0.9600
C15—C16	1.370 (4)	C10—H10	0.9300
C15—C20	1.376 (5)	C17—H17	0.9300
C4—C3	1.396 (4)	C19—H19	0.9300
C4—C5	1.438 (4)	C21—H21A	0.9600
C5—C6	1.508 (4)	C21—H21B	0.9600
C18—C17	1.371 (5)	C21—H21C	0.9600
C3—N2—N1	110.0 (2)	C10—C11—H11	119.4
C3—N2—C7	129.8 (3)	C12—C11—H11	119.4
N1—N2—C7	119.7 (3)	C15—C20—C19	120.8 (3)
C3—O3—H3	109.5	C15—C20—H20	119.6
C5—N1—N2	106.5 (2)	C19—C20—H20	119.6
C8—C7—C12	120.3 (3)	O3—C3—N2	123.5 (3)
C8—C7—N2	118.6 (3)	O3—C3—C4	128.3 (3)
C12—C7—N2	121.1 (3)	N2—C3—C4	108.2 (3)
O14—C14—C4	118.5 (3)	C11—C12—C7	119.6 (4)
O14—C14—C15	117.6 (3)	C11—C12—H12	120.2
C4—C14—C15	123.9 (3)	C7—C12—H12	120.2
C9—C8—C7	118.6 (3)	C5—C6—H6A	109.5
C9—C8—H8	120.7	C5—C6—H6B	109.5
C7—C8—H8	120.7	H6A—C6—H6B	109.5
C16—C15—C20	118.8 (3)	C5—C6—H6C	109.5
C16—C15—C14	120.4 (3)	H6A—C6—H6C	109.5
C20—C15—C14	120.8 (3)	H6B—C6—H6C	109.5
C3—C4—C14	119.5 (3)	C11—C10—C9	118.5 (3)
C3—C4—C5	103.9 (3)	C11—C10—H10	120.7
C14—C4—C5	136.4 (3)	C9—C10—H10	120.7
N1—C5—C4	111.3 (3)	C18—C17—C16	121.7 (4)
N1—C5—C6	118.3 (3)	C18—C17—H17	119.2
C4—C5—C6	130.2 (3)	C16—C17—H17	119.2
C17—C18—C19	118.1 (4)	C18—C19—C20	120.5 (4)
C17—C18—C21	121.9 (4)	C18—C19—H19	119.7
C19—C18—C21	120.0 (4)	C20—C19—H19	119.7
C15—C16—C17	120.1 (4)	C18—C21—H21A	109.5
C15—C16—H16	119.9	C18—C21—H21B	109.5
C17—C16—H16	119.9	H21A—C21—H21B	109.5
C8—C9—C10	121.7 (4)	C18—C21—H21C	109.5
C8—C9—Cl1	118.7 (3)	H21A—C21—H21C	109.5
C10—C9—Cl1	119.5 (3)	H21B—C21—H21C	109.5
C10—C11—C12	121.2 (4)
C3—N2—N1—C5	1.8 (4)	C7—C8—C9—C10	−1.0 (6)
C7—N2—N1—C5	174.8 (3)	C7—C8—C9—Cl1	177.9 (3)
C3—N2—C7—C8	158.0 (4)	C16—C15—C20—C19	−1.4 (5)
N1—N2—C7—C8	−13.5 (5)	C14—C15—C20—C19	−179.0 (3)
C3—N2—C7—C12	−21.7 (5)	N1—N2—C3—O3	177.2 (3)
N1—N2—C7—C12	166.8 (3)	C7—N2—C3—O3	5.1 (6)
C12—C7—C8—C9	1.5 (5)	N1—N2—C3—C4	−2.2 (4)
N2—C7—C8—C9	−178.3 (3)	C7—N2—C3—C4	−174.3 (3)
O14—C14—C15—C16	−41.9 (5)	C14—C4—C3—O3	−2.2 (6)
C4—C14—C15—C16	138.7 (4)	C5—C4—C3—O3	−177.7 (4)
O14—C14—C15—C20	135.7 (4)	C14—C4—C3—N2	177.1 (3)
C4—C14—C15—C20	−43.8 (5)	C5—C4—C3—N2	1.7 (4)
O14—C14—C4—C3	−6.5 (5)	C10—C11—C12—C7	1.8 (6)
C15—C14—C4—C3	173.0 (3)	C8—C7—C12—C11	−1.8 (5)
O14—C14—C4—C5	167.1 (4)	N2—C7—C12—C11	177.9 (3)
C15—C14—C4—C5	−13.5 (7)	C12—C11—C10—C9	−1.3 (6)
N2—N1—C5—C4	−0.7 (4)	C8—C9—C10—C11	1.0 (6)
N2—N1—C5—C6	−177.1 (3)	Cl1—C9—C10—C11	−178.0 (3)
C3—C4—C5—N1	−0.6 (4)	C19—C18—C17—C16	0.3 (6)
C14—C4—C5—N1	−174.9 (4)	C21—C18—C17—C16	−179.1 (3)
C3—C4—C5—C6	175.3 (4)	C15—C16—C17—C18	−1.7 (5)
C14—C4—C5—C6	1.0 (7)	C17—C18—C19—C20	0.5 (5)
C20—C15—C16—C17	2.2 (5)	C21—C18—C19—C20	179.9 (3)
C14—C15—C16—C17	179.8 (3)	C15—C20—C19—C18	0.1 (5)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O14	0.82	1.90	2.581 (3)	140

Table 1

Hydrogen-bond geometry (, )

DHA	DH	HA	D A	DHA
O3H3O14	0.82	1.90	2.581(3)	140