Crystal structure of (4Z)-4-[(2E)-3-(2-chloro­phen­yl)-1-hy­droxy­prop-2-en-1-yl­idene]-3-methyl-1-phenyl-1H-pyrazol-5(4H)-one

Shahid, M.; Munawar, M.A.; Tahir, M.N.; Salim, M.; Malik, K.I.

doi:10.1107/S2056989015009020

organic compounds

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ISSN: 2056-9890

Volume 71| Part 6| June 2015| Pages o407-o408

doi:10.1107/S2056989015009020

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Crystal structure of (4Z)-4-[(2E)-3-(2-chlorophenyl)-1-hydroxyprop-2-en-1-ylidene]-3-methyl-1-phenyl-1H-pyrazol-5(4H)-one

Muhammad Shahid,^a Munawar Ali Munawar,^a Muhammad Nawaz Tahir,^b ^* Muhammad Salim ^a and Khizar Iqbal Malik ^a

^aDepartment of Chemistry, University of the Punjab, Lahore, Punjab, Pakistan, and ^bDepartment of Physics, University of Sargodha, Sargodha, Punjab, Pakistan
^*Correspondence e-mail: dmntahir_uos@yahoo.com

Edited by W. T. A. Harrison, University of Aberdeen, Scotland (Received 6 May 2015; accepted 11 May 2015; online 20 May 2015)

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 chlorobenzene rings, respectively. An intramolecular O—H⋯O hydrogen bond closes an S(6) ring and a short C—H⋯O contact is also observed. In the crystal, molecules are linked by weak C—H⋯O interactions to generate (001) sheets. Weak aromatic π–π interactions between the chlorobenzene and pyrazole rings, with a centroid–centroid distance of 3.7956 (17) Å are also observed.

Keywords: crystal structure; pyrazole; hydrogen bonding; π–π interactions.

CCDC reference: 1400008

1. Related literature

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

2. Experimental

2.1. Crystal data

C₁₉H₁₅ClN₂O₂
M_r = 338.78
Orthorhombic, P 2₁ 2₁ 2₁
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

2.2. 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

2.3. Refinement

R[F² > 2σ(F²)] = 0.043
wR(F²) = 0.091
S = 1.00
3593 reflections
219 parameters
H-atom parameters constrained
Δρ_max = 0.13 e Å⁻³
Δρ_min = −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)

Table 1
Hydrogen-bond geometry (Å, °)

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
Symmetry codes: (i) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[-x, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

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.

Supporting information

CCDC reference: 1400008

Crystal structure: contains datablocks global, I. DOI: 10.1107/S2056989015009020/hb7419sup1.cif

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

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

checkCIF report

Comment top

The crystal structures of 5-methyl-2-phenyl-4-((E)-3-phenyl-2-hydroxy- prop-2-enylidene)-1,2-dihydro-3H-pyrazol-3-one (Holzer et al., 1999), (4Z)-4-((2E)-1-hydroxy-3-(4-methoxyphenyl)prop-2-en-1- ylidene)-3-methyl-1-phenyl-1H-pyrazol-5(4H)-one (Malik et al., 2009) and (4Z)-4-((2E)-1-hydroxy-3-(3-nitrophenyl)prop- 2-en-1-ylidene)-3-methyl-1-(4-methylphenyl)-1H-pyrazol-5(4H)-one (Chaudhry, et al., 2012) have been published which are related to the title compound (I, Fig. 1). (I) is synthesized for the biological studies as well as for the preparation of different metal complexes.

In (I), the benzene ring A (C1–C6) and the 4-[(2E)-3-(2-chlorophenyl)-1- hydroxyprop-2-en-1-ylidene]-5-methyl-2,4-dihydro-3H-pyrazol-3-one moiety (C7 –C19/N1/N2/O1/O2/CL1) are planar with r. m. s. deviation of 0.0016 and 0.0158 Å, respectively. The dihedral angle between A/B is 4.87 (14)°. There exist intramolecular H-bonding of O—H···O type completing S (6) loop (Bernstein et al., 1995). The molecules are interlimked due to C—H···O interactions (Table 1, Fig. 2). There exist π–π interactions at a distance of 3.7956 (17) Å between the centeroids of Cg1—Cg2ⁱ and Cg2— Cg1ⁱⁱ [i = 1 + x, y, z and ii = -1 + x, y, z], where Cg1 and Cg2 are the centroids of heterocyclic ring C (N1/N2/C7/C8/C9) and chloro containing benzene ring D (C14–C19), respectively.

Related literature top

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

Experimental top

4-Acetyl-3-methyl-1-phenyl-5-hydroxypyrazole (0.218 g, 1 mmol), 2-chlorobenzaldehyde (0.211 g, 1.5 mmol) in glacial acetic acid (10 ml) and concentrated sulfuric acid (0.2 ml) was stirred at 353–360 K for 6 h. The reaction mixture was diluted with distilled water (50 ml). The precipitate was filtered, washed with methanol and dried. The crude product was purified by column chromatography using n-hexane and ethyl acetate mixtures as eluents. The product was recrystallized from n-hexane solution to afford yellow plates. Yield = 60%; m.p. 453 K

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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 (Spek, 2009).

Figures top

	Fig. 1. View of the title compound with displacement ellipsoids drawn at the 50% probability level.
	Fig. 2. The partial packing, which shows that molecules are interlinked due to O—H···O bondings.

(4Z)-4-[(2E)-3-(2-Chlorophenyl)-1-hydroxyprop-2-en-1-ylidene]-3-methyl-1-phenyl-1H-pyrazol-5(4H)-one top

Crystal data top

C₁₉H₁₅ClN₂O₂	D_x = 1.358 Mg m⁻³
M_r = 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

Data collection top

Bruker Kappa APEXII CCD diffractometer	3593 independent reflections
Radiation source: fine-focus sealed tube	2455 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.034
Detector resolution: 7.70 pixels mm^-1	θ_max = 27.0°, θ_min = 2.3°
ω scans	h = −8→9
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −16→13
T_min = 0.923, T_max = 0.960	l = −22→20
8199 measured reflections

Refinement top

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(F_o²) + (0.0369P)²] where P = (F_o² + 2F_c²)/3
S = 1.00	(Δ/σ)_max < 0.001
3593 reflections	Δρ_max = 0.13 e Å⁻³
219 parameters	Δρ_min = −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)

Crystal data top

C₁₉H₁₅ClN₂O₂	V = 1656.41 (12) Å³
M_r = 338.78	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 7.2348 (3) Å	µ = 0.24 mm⁻¹
b = 12.8737 (6) Å	T = 296 K
c = 17.7843 (7) Å	0.34 × 0.28 × 0.16 mm

Data collection top

Bruker Kappa APEXII CCD diffractometer	3593 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	2455 reflections with I > 2σ(I)
T_min = 0.923, T_max = 0.960	R_int = 0.034
8199 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.043	H-atom parameters constrained
wR(F²) = 0.091	Δρ_max = 0.13 e Å⁻³
S = 1.00	Δρ_min = −0.17 e Å⁻³
3593 reflections	Absolute structure: Flack x determined using 771 quotients [(I⁺)-(I^-)]/[(I⁺)+(I^-)] (Parsons et al., 2013)
219 parameters	Absolute structure parameter: −0.06 (4)
0 restraints

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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

Symmetry codes: (i) −x+1, y−1/2, −z+1/2; (ii) −x, y−1/2, −z+1/2.

Hydrogen-bond geometry (Å, º) top

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

Symmetry codes: (i) −x+1, y−1/2, −z+1/2; (ii) −x, y−1/2, −z+1/2.

Acknowledgements

The authors acknowledge the provision of funds for the purchase of the diffractometer and encouragement by Dr Muhammad Akram Chaudhary, Vice Chancellor, University of Sargodha, Pakistan.

References

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Volume 71| Part 6| June 2015| Pages o407-o408

doi:10.1107/S2056989015009020

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Crystal structure of (4Z)-4-[(2E)-3-(2-chloro­phen­yl)-1-hy­dr­oxy­prop-2-en-1-yl­­idene]-3-methyl-1-phenyl-1H-pyrazol-5(4H)-one

1. Related literature

2. Experimental

2.1. Crystal data

2.2. Data collection

2.3. Refinement

Supporting information

Acknowledgements

References

organic compounds

Crystal structure of (4Z)-4-[(2E)-3-(2-chlorophenyl)-1-hydroxyprop-2-en-1-ylidene]-3-methyl-1-phenyl-1H-pyrazol-5(4H)-one