Crystal structure of (4Z)-4-[(2E)-3-(2-chloro-phen-yl)-1-hy-droxy-prop-2-en-1-yl-idene]-3-methyl-1-phenyl-1H-pyrazol-5(4H)-one.

In the title compound, C19H15ClN2O2, the pyrazole ring is almost planar (r.m.s. deviation = 0.002 Å) and subtends dihedral angles of 5.31 (16) and 1.86 (16)° with the phenyl and chloro-benzene rings, respectively. An intra-molecular O-H⋯O hydrogen bond closes an S(6) ring and a short C-H⋯O contact is also observed. In the crystal, mol-ecules are linked by weak C-H⋯O inter-actions to generate (001) sheets. Weak aromatic π-π inter-actions between the chloro-benzene and pyrazole rings, with a centroid-centroid distance of 3.7956 (17) Å are also observed.

Related literature

For related structures, see: Chaudhry et al. (2012 ▸); Holzer et al. (1999 ▸); Malik et al. (2009 ▸).

Experimental

Crystal data

C19H15ClN2O2

M = 338.78

Orthorhombic,

a = 7.2348 (3) Å

b = 12.8737 (6) Å

c = 17.7843 (7) Å

V = 1656.41 (12) Å3

Z = 4

Mo Kα radiation

μ = 0.24 mm−1

T = 296 K

0.34 × 0.28 × 0.16 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▸) T min = 0.923, T max = 0.960

8199 measured reflections

3593 independent reflections

2455 reflections with I > 2σ(I)

R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.091

S = 1.00

3593 reflections

219 parameters

H-atom parameters constrained

Δρmax = 0.13 e Å−3

Δρmin = −0.17 e Å−3

Absolute structure: Flack x determined using 771 quotients [(I +)−(I −)]/[(I +)+(I −)] (Parsons et al., 2013 ▸)

Absolute structure parameter: −0.06 (4)

Data collection: APEX2 (Bruker, 2007 ▸); cell refinement: SAINT (Bruker, 2007 ▸); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▸); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015 ▸); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▸) and PLATON (Spek, 2009 ▸); software used to prepare material for publication: WinGX (Farrugia, 2012 ▸) and PLATON.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S2056989015009020/hb7419sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015009020/hb7419Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S2056989015009020/hb7419Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S2056989015009020/hb7419fig1.tif

View of the title compound with displacement ellipsoids drawn at the 50% probability level.

Click here for additional data file.

. DOI: 10.1107/S2056989015009020/hb7419fig2.tif

The partial packing, which shows that mol­ecules are inter­linked due to O—H⋯O bondings.

CCDC reference: 1400008

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

C19H15ClN2O2	Dx = 1.358 Mg m−3
Mr = 338.78	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121	Cell parameters from 2455 reflections
a = 7.2348 (3) Å	θ = 2.3–27.0°
b = 12.8737 (6) Å	µ = 0.24 mm−1
c = 17.7843 (7) Å	T = 296 K
V = 1656.41 (12) Å3	Plate, yellow
Z = 4	0.34 × 0.28 × 0.16 mm
F(000) = 704

Bruker Kappa APEXII CCD diffractometer	3593 independent reflections
Radiation source: fine-focus sealed tube	2455 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.034
Detector resolution: 7.70 pixels mm-1	θmax = 27.0°, θmin = 2.3°
ω scans	h = −8→9
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −16→13
Tmin = 0.923, Tmax = 0.960	l = −22→20
8199 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)] = 0.043	H-atom parameters constrained
wR(F2) = 0.091	w = 1/[σ2(Fo2) + (0.0369P)2] where P = (Fo2 + 2Fc2)/3
S = 1.00	(Δ/σ)max < 0.001
3593 reflections	Δρmax = 0.13 e Å−3
219 parameters	Δρmin = −0.17 e Å−3
0 restraints	Absolute structure: Flack x determined using 771 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.06 (4)

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
C1	1.0397 (4)	0.0392 (2)	0.44274 (15)	0.0467 (7)
C2	1.1377 (5)	−0.0394 (3)	0.47830 (17)	0.0585 (9)
H2	1.0927	−0.1070	0.4786	0.070*
C3	1.3019 (5)	−0.0158 (3)	0.5130 (2)	0.0757 (11)
H3	1.3684	−0.0684	0.5366	0.091*
C4	1.3695 (5)	0.0835 (4)	0.51358 (19)	0.0788 (11)
H4	1.4806	0.0983	0.5376	0.095*
C5	1.2721 (5)	0.1611 (3)	0.47842 (19)	0.0754 (11)
H5	1.3174	0.2287	0.4786	0.091*
C6	1.1075 (5)	0.1391 (3)	0.44288 (18)	0.0612 (9)
H6	1.0421	0.1918	0.4190	0.073*
C7	0.7566 (4)	0.0745 (2)	0.36469 (16)	0.0472 (7)
C8	0.6056 (4)	0.0103 (2)	0.34325 (16)	0.0454 (7)
C9	0.6447 (4)	−0.0886 (2)	0.37664 (16)	0.0495 (7)
C10	0.5360 (5)	−0.1872 (2)	0.37362 (19)	0.0705 (10)
H10A	0.5947	−0.2387	0.4045	0.106*
H10B	0.5305	−0.2115	0.3226	0.106*
H10C	0.4130	−0.1747	0.3918	0.106*
C11	0.4645 (4)	0.0533 (2)	0.29952 (16)	0.0492 (8)
C12	0.3000 (4)	−0.0007 (3)	0.27371 (16)	0.0512 (8)
H12	0.2835	−0.0702	0.2864	0.061*
C13	0.1726 (4)	0.0468 (3)	0.23235 (17)	0.0507 (8)
H13	0.1955	0.1162	0.2212	0.061*
C14	0.0018 (4)	0.0040 (2)	0.20232 (15)	0.0455 (8)
C15	−0.0492 (5)	−0.0993 (3)	0.21263 (16)	0.0572 (8)
H15	0.0281	−0.1428	0.2400	0.069*
C16	−0.2102 (5)	−0.1386 (3)	0.18351 (18)	0.0649 (10)
H16	−0.2405	−0.2080	0.1912	0.078*
C17	−0.3274 (5)	−0.0754 (3)	0.1427 (2)	0.0672 (10)
H17	−0.4368	−0.1020	0.1232	0.081*
C18	−0.2818 (5)	0.0269 (3)	0.13120 (18)	0.0625 (9)
H18	−0.3598	0.0699	0.1036	0.075*
C19	−0.1203 (4)	0.0655 (2)	0.16072 (15)	0.0481 (8)
Cl1	−0.06694 (12)	0.19522 (6)	0.14234 (5)	0.0687 (3)
N1	0.8699 (3)	0.01404 (19)	0.40719 (13)	0.0472 (6)
N2	0.7992 (4)	−0.0870 (2)	0.41388 (14)	0.0539 (7)
O1	0.7814 (3)	0.16964 (16)	0.34743 (13)	0.0638 (6)
O2	0.4797 (3)	0.15046 (17)	0.28011 (14)	0.0659 (7)
H2A	0.5725	0.1754	0.2995	0.099*

	U11	U22	U33	U12	U13	U23
C1	0.0501 (18)	0.0511 (19)	0.0389 (15)	0.0025 (16)	−0.0027 (14)	−0.0056 (14)
C2	0.065 (2)	0.060 (2)	0.0516 (18)	0.0003 (18)	−0.0134 (17)	0.0015 (16)
C3	0.078 (3)	0.083 (3)	0.065 (2)	0.009 (2)	−0.030 (2)	0.005 (2)
C4	0.067 (2)	0.097 (3)	0.072 (2)	−0.009 (2)	−0.028 (2)	0.000 (2)
C5	0.076 (3)	0.075 (3)	0.076 (2)	−0.018 (2)	−0.020 (2)	−0.003 (2)
C6	0.063 (2)	0.059 (2)	0.062 (2)	−0.0041 (17)	−0.0131 (18)	−0.0029 (17)
C7	0.0489 (18)	0.0464 (19)	0.0461 (16)	0.0063 (15)	−0.0043 (15)	−0.0001 (15)
C8	0.0464 (18)	0.0436 (18)	0.0463 (16)	0.0051 (14)	−0.0026 (14)	−0.0017 (14)
C9	0.0484 (18)	0.0452 (18)	0.0549 (18)	0.0022 (15)	−0.0027 (15)	−0.0021 (15)
C10	0.071 (2)	0.048 (2)	0.093 (3)	−0.0056 (19)	−0.021 (2)	0.0053 (19)
C11	0.0522 (19)	0.0455 (19)	0.0500 (17)	0.0059 (16)	0.0014 (15)	−0.0019 (14)
C12	0.0507 (19)	0.049 (2)	0.0538 (17)	0.0027 (16)	−0.0040 (16)	0.0020 (16)
C13	0.049 (2)	0.051 (2)	0.0522 (17)	0.0037 (16)	−0.0020 (15)	0.0016 (15)
C14	0.0431 (18)	0.051 (2)	0.0422 (15)	0.0051 (15)	0.0016 (13)	−0.0021 (14)
C15	0.060 (2)	0.056 (2)	0.0559 (19)	0.0020 (19)	0.0010 (17)	0.0079 (16)
C16	0.067 (2)	0.060 (2)	0.068 (2)	−0.015 (2)	0.007 (2)	−0.0019 (18)
C17	0.051 (2)	0.079 (3)	0.072 (2)	−0.009 (2)	0.0011 (18)	−0.016 (2)
C18	0.053 (2)	0.070 (2)	0.064 (2)	0.0112 (18)	−0.0118 (17)	−0.0112 (19)
C19	0.0488 (18)	0.045 (2)	0.0500 (17)	0.0073 (15)	0.0004 (15)	−0.0081 (15)
Cl1	0.0766 (6)	0.0463 (5)	0.0832 (6)	0.0147 (5)	−0.0178 (5)	−0.0019 (5)
N1	0.0470 (15)	0.0445 (16)	0.0502 (14)	0.0025 (12)	−0.0078 (12)	−0.0009 (12)
N2	0.0547 (16)	0.0438 (16)	0.0631 (17)	−0.0022 (14)	−0.0102 (13)	0.0033 (13)
O1	0.0687 (14)	0.0432 (13)	0.0794 (15)	−0.0022 (11)	−0.0151 (13)	0.0083 (12)
O2	0.0594 (15)	0.0523 (15)	0.0860 (17)	0.0026 (11)	−0.0196 (13)	0.0104 (13)

C1—C6	1.377 (4)	C10—H10C	0.9600
C1—C2	1.387 (4)	C11—O2	1.302 (3)
C1—N1	1.419 (4)	C11—C12	1.453 (4)
C2—C3	1.372 (4)	C12—C13	1.328 (4)
C2—H2	0.9300	C12—H12	0.9300
C3—C4	1.370 (5)	C13—C14	1.454 (4)
C3—H3	0.9300	C13—H13	0.9300
C4—C5	1.373 (5)	C14—C15	1.392 (4)
C4—H4	0.9300	C14—C19	1.398 (4)
C5—C6	1.377 (4)	C15—C16	1.372 (5)
C5—H5	0.9300	C15—H15	0.9300
C6—H6	0.9300	C16—C17	1.381 (5)
C7—O1	1.276 (3)	C16—H16	0.9300
C7—N1	1.360 (3)	C17—C18	1.373 (5)
C7—C8	1.421 (4)	C17—H17	0.9300
C8—C11	1.397 (4)	C18—C19	1.374 (4)
C8—C9	1.433 (4)	C18—H18	0.9300
C9—N2	1.299 (4)	C19—Cl1	1.745 (3)
C9—C10	1.494 (4)	N1—N2	1.403 (3)
C10—H10A	0.9600	O2—H2A	0.8200
C10—H10B	0.9600
C6—C1—C2	119.9 (3)	O2—C11—C8	117.8 (3)
C6—C1—N1	121.5 (3)	O2—C11—C12	116.4 (3)
C2—C1—N1	118.6 (3)	C8—C11—C12	125.8 (3)
C3—C2—C1	119.1 (3)	C13—C12—C11	121.6 (3)
C3—C2—H2	120.4	C13—C12—H12	119.2
C1—C2—H2	120.4	C11—C12—H12	119.2
C4—C3—C2	121.2 (4)	C12—C13—C14	128.2 (3)
C4—C3—H3	119.4	C12—C13—H13	115.9
C2—C3—H3	119.4	C14—C13—H13	115.9
C3—C4—C5	119.5 (4)	C15—C14—C19	116.3 (3)
C3—C4—H4	120.2	C15—C14—C13	122.6 (3)
C5—C4—H4	120.2	C19—C14—C13	121.1 (3)
C4—C5—C6	120.2 (4)	C16—C15—C14	121.9 (3)
C4—C5—H5	119.9	C16—C15—H15	119.1
C6—C5—H5	119.9	C14—C15—H15	119.1
C1—C6—C5	120.0 (3)	C15—C16—C17	120.1 (3)
C1—C6—H6	120.0	C15—C16—H16	119.9
C5—C6—H6	120.0	C17—C16—H16	119.9
O1—C7—N1	126.8 (3)	C18—C17—C16	119.8 (3)
O1—C7—C8	127.0 (3)	C18—C17—H17	120.1
N1—C7—C8	106.3 (3)	C16—C17—H17	120.1
C11—C8—C7	118.8 (3)	C17—C18—C19	119.6 (3)
C11—C8—C9	136.6 (3)	C17—C18—H18	120.2
C7—C8—C9	104.7 (3)	C19—C18—H18	120.2
N2—C9—C8	111.5 (3)	C18—C19—C14	122.4 (3)
N2—C9—C10	118.9 (3)	C18—C19—Cl1	117.5 (2)
C8—C9—C10	129.5 (3)	C14—C19—Cl1	120.1 (2)
C9—C10—H10A	109.5	C7—N1—N2	111.0 (2)
C9—C10—H10B	109.5	C7—N1—C1	129.7 (3)
H10A—C10—H10B	109.5	N2—N1—C1	119.3 (2)
C9—C10—H10C	109.5	C9—N2—N1	106.5 (2)
H10A—C10—H10C	109.5	C11—O2—H2A	109.5
H10B—C10—H10C	109.5
C6—C1—C2—C3	−0.2 (5)	C12—C13—C14—C19	178.7 (3)
N1—C1—C2—C3	−179.9 (3)	C19—C14—C15—C16	0.1 (4)
C1—C2—C3—C4	0.5 (5)	C13—C14—C15—C16	−179.6 (3)
C2—C3—C4—C5	−0.4 (6)	C14—C15—C16—C17	−0.1 (5)
C3—C4—C5—C6	0.0 (6)	C15—C16—C17—C18	0.3 (5)
C2—C1—C6—C5	−0.1 (5)	C16—C17—C18—C19	−0.3 (5)
N1—C1—C6—C5	179.5 (3)	C17—C18—C19—C14	0.3 (5)
C4—C5—C6—C1	0.2 (5)	C17—C18—C19—Cl1	178.5 (2)
O1—C7—C8—C11	−1.1 (5)	C15—C14—C19—C18	−0.2 (4)
N1—C7—C8—C11	179.1 (2)	C13—C14—C19—C18	179.5 (3)
O1—C7—C8—C9	179.7 (3)	C15—C14—C19—Cl1	−178.3 (2)
N1—C7—C8—C9	−0.1 (3)	C13—C14—C19—Cl1	1.3 (4)
C11—C8—C9—N2	−179.1 (3)	O1—C7—N1—N2	−179.5 (3)
C7—C8—C9—N2	−0.1 (3)	C8—C7—N1—N2	0.3 (3)
C11—C8—C9—C10	1.1 (6)	O1—C7—N1—C1	0.2 (5)
C7—C8—C9—C10	−179.8 (3)	C8—C7—N1—C1	−180.0 (2)
C7—C8—C11—O2	0.5 (4)	C6—C1—N1—C7	5.6 (5)
C9—C8—C11—O2	179.4 (3)	C2—C1—N1—C7	−174.8 (3)
C7—C8—C11—C12	−179.1 (3)	C6—C1—N1—N2	−174.8 (3)
C9—C8—C11—C12	−0.2 (5)	C2—C1—N1—N2	4.9 (4)
O2—C11—C12—C13	0.2 (5)	C8—C9—N2—N1	0.3 (3)
C8—C11—C12—C13	179.8 (3)	C10—C9—N2—N1	−179.9 (2)
C11—C12—C13—C14	180.0 (3)	C7—N1—N2—C9	−0.4 (3)
C12—C13—C14—C15	−1.7 (5)	C1—N1—N2—C9	179.9 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2A···O1	0.82	1.74	2.501 (3)	154
C6—H6···O1	0.93	2.29	2.933 (4)	126
C10—H10B···O2i	0.96	2.55	3.444 (4)	155
C16—H16···O2ii	0.93	2.56	3.405 (4)	151

Table 1

Hydrogen-bond geometry (, )

DHA	DH	HA	D A	DHA
O2H2AO1	0.82	1.74	2.501(3)	154
C6H6O1	0.93	2.29	2.933(4)	126
C10H10BO2i	0.96	2.55	3.444(4)	155
C16H16O2ii	0.93	2.56	3.405(4)	151

Symmetry codes: (i) ; (ii) .