(4Z)-4-[(2E)-1-Hydr­oxy-3-(4-methoxy­phen­yl)prop-2-en­ylidene]-3-methyl-1-phenyl-1H-pyrazol-5(4H)-one

Malik, K.I.; Munawar, M.A.; Khan, M.A.; Nadeem, S.; Mukhtar-ul-Hassan

doi:10.1107/S1600536809046200

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 65| Part 12| December 2009| Page o3046

doi:10.1107/S1600536809046200

Open

access

(4Z)-4-[(2E)-1-Hydroxy-3-(4-methoxyphenyl)prop-2-enylidene]-3-methyl-1-phenyl-1H-pyrazol-5(4H)-one

Khizar Iqbal Malik,^a Munawar Ali Munawar,^a ^* Misbahul Ain Khan,^a Sohail Nadeem ^a and Mukhtar-ul-Hassan ^a

^aInstitute of Chemistry, University of the Punjab, New Campus, Lahore, Pakistan
^*Correspondence e-mail: munawaralimunawar@yahoo.com

(Received 7 October 2009; accepted 3 November 2009; online 11 November 2009)

The title compound, C₂₀H₁₈N₂O₄, is a chalcone derivative of pyrazole. The pyrazole ring is inclined at a dihedral angle of 19.29 (12)° to the methoxyphenyl ring mean plane, and by 1.19 (13)° to the phenyl ring. The molecular structure is stabilized by an intramolecular O—H⋯O hydrogen bond, making an almost planar (r.m.s. deviation = 0.0243 Å) six membered ring.

Related literature

For the antimicrobial activity of chalcones, see: Mityurina1 et al. (1981 ). For the syntheses of chalcones, see: Konieczny et al. (2007 ). For a heterocyclic chalcone, see: Arshad et al. (2008 ). For details concerning graphset analysis, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₂₀H₁₈N₂O₃
M_r = 334.36
Monoclinic, C c
a = 5.0803 (2) Å
b = 22.7645 (9) Å
c = 14.5880 (6) Å
β = 97.626 (2)°
V = 1672.19 (12) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 296 K
0.33 × 0.24 × 0.18 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ) T_min = 0.971, T_max = 0.984
9137 measured reflections
2056 independent reflections
2628 reflections with I > 2σ(I)
R_int = 0.027

Refinement

R[F² > 2σ(F²)] = 0.037
wR(F²) = 0.094
S = 1.05
2056 reflections
229 parameters
2 restraints
H-atom parameters constrained
Δρ_max = 0.10 e Å⁻³
Δρ_min = −0.16 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2O⋯O1	0.82	1.77	2.529 (3)	153

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: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ) and PLATON.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809046200/su2151sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809046200/su2151Isup2.hkl

checkCIF report

Comment top

Pyranopyrazole derivatives have been reported as being antimicrobial agents (Mityurina1 et al., 1981). The title compound is a heterocyclic chalcone (Arshad et al., 2008), and was synthesized as we are interested in the synthesis of pyranopyrazole derivatives.

The molecular structure of the title compound is illustrated in Fig. 1, and the geometrical parameters are available in the archived CIF. The title molecule, besides the methoxy phenyl ring A (C13-C18) attached to the pyrazole ring, is almost planar. The dihedral angle between the pyrazole ring B (N1/N2/C10-C12) and phenyl ring A is 19.29 (12) °. Phenyl ring C (C1-C6) lies in the plane of the pyrazole ring B, with a dihedral angle of 1.19 (13)°. There is an intramolecular O-H···O hydrogen bond stabilizing the molecule (Fig. 1 and Table 1). It forms a six membered ring motif which can be described as S(6) (Bernstein, et al., 1995).

Related literature top

For the antimicrobial activity of chalcones, see: Mityurina1 et al. (1981). For the syntheses of chalcones, see: Konieczny et al. (2007). For a hereocyclic chalcone, see: Arshad et al. (2008). For details concerning graphset analysis, see: Bernstein et al. (1995).

Experimental top

The title compound was prepared according to the literature method (Konieczny et al., 2007). 1 mmol (0.216 g) of 3-methyl-1-phenyl-acetyl-5-hydroxy pyrazole and 1.5 mmol (0.204 g) of 4-methoxybenzaldehyde was added to the mixture of 2 ml of glacial acetic acid and 0.2 ml of concentrated sulfuric acid and heated at 353-358 K for 9 h with stirring. The progress of the reaction was followed by TLC. On completion, the mixture was added to ice cold water. The precipitate obtained was filtered off, washed with methanol and purified by column chromatography using n-hexane:ethyl acetate(3:2). Red needle-like crystals, suitable for X-ray analysis, were obtained by slow evaporation of a solution in chloroform at r.t.

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: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Figures top

Fig. 1. The molecular structure of the title compound, with thermal ellipsoids drawn at the 50% probability level. The intramolecular O-H···O hydrogen bond is shown as a dashed line.

(4Z)-4-[(2E)-1-Hydroxy-3-(4-methoxyphenyl)prop-2-enylidene]-3-methyl-1-phenyl-1H-pyrazol-5(4H)-one top

Crystal data top

C₂₀H₁₈N₂O₃	F(000) = 704
M_r = 334.36	D_x = 1.328 Mg m⁻³
Monoclinic, Cc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2yc	Cell parameters from 3228 reflections
a = 5.0803 (2) Å	θ = 2.3–25.8°
b = 22.7645 (9) Å	µ = 0.09 mm⁻¹
c = 14.5880 (6) Å	T = 296 K
β = 97.626 (2)°	Needle, red
V = 1672.19 (12) Å³	0.33 × 0.24 × 0.18 mm
Z = 4

Data collection top

Bruker Kappa APEXII CCD diffractometer	2056 independent reflections
Radiation source: fine-focus sealed tube	2628 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.027
ϕ and ω scans	θ_max = 28.3°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −6→6
T_min = 0.971, T_max = 0.984	k = −30→30
9137 measured reflections	l = −18→18

Refinement top

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.094	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0492P)² + 0.0958P] where P = (F_o² + 2F_c²)/3
2056 reflections	(Δ/σ)_max < 0.001
229 parameters	Δρ_max = 0.10 e Å⁻³
2 restraints	Δρ_min = −0.16 e Å⁻³

Crystal data top

C₂₀H₁₈N₂O₃	V = 1672.19 (12) Å³
M_r = 334.36	Z = 4
Monoclinic, Cc	Mo Kα radiation
a = 5.0803 (2) Å	µ = 0.09 mm⁻¹
b = 22.7645 (9) Å	T = 296 K
c = 14.5880 (6) Å	0.33 × 0.24 × 0.18 mm
β = 97.626 (2)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	2056 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	2628 reflections with I > 2σ(I)
T_min = 0.971, T_max = 0.984	R_int = 0.027
9137 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	2 restraints
wR(F²) = 0.094	H-atom parameters constrained
S = 1.05	Δρ_max = 0.10 e Å⁻³
2056 reflections	Δρ_min = −0.16 e Å⁻³
229 parameters

Special details top

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 esds are taken into account in the estimation of distances, angles and torsion angles

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 > 2σ(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
O1	−0.0176 (4)	0.44681 (8)	0.51341 (14)	0.0664 (7)
O2	0.3841 (4)	0.46097 (8)	0.63360 (16)	0.0711 (7)
O3	1.6238 (3)	0.37711 (9)	1.04514 (13)	0.0698 (7)
N1	−0.1696 (3)	0.34974 (9)	0.51051 (14)	0.0509 (7)
N2	−0.0989 (4)	0.29740 (9)	0.55796 (15)	0.0553 (7)
C1	1.0015 (4)	0.41049 (11)	0.83769 (17)	0.0485 (7)
C2	1.0508 (5)	0.35476 (12)	0.8761 (2)	0.0582 (9)
C3	1.2597 (5)	0.34518 (11)	0.9444 (2)	0.0596 (9)
C4	1.4271 (4)	0.39123 (12)	0.97629 (17)	0.0525 (8)
C5	1.3838 (4)	0.44665 (10)	0.93893 (17)	0.0493 (8)
C6	1.1739 (4)	0.45543 (11)	0.87062 (17)	0.0503 (8)
C7	0.7813 (4)	0.42297 (12)	0.76621 (17)	0.0509 (8)
C8	0.5954 (4)	0.38652 (12)	0.72645 (17)	0.0520 (8)
C9	0.3848 (4)	0.40523 (12)	0.65663 (17)	0.0520 (8)
C10	0.1866 (4)	0.36961 (11)	0.61184 (16)	0.0476 (7)
C11	0.1116 (4)	0.30908 (11)	0.61679 (17)	0.0499 (8)
C12	−0.0042 (4)	0.39408 (11)	0.54131 (16)	0.0508 (8)
C13	−0.3813 (4)	0.34899 (10)	0.43652 (17)	0.0495 (8)
C14	−0.5624 (5)	0.30347 (11)	0.43192 (19)	0.0546 (8)
C15	−0.7691 (5)	0.30167 (13)	0.3600 (2)	0.0689 (10)
C16	−0.7933 (6)	0.34472 (14)	0.2929 (2)	0.0789 (11)
C17	−0.6134 (6)	0.38955 (15)	0.2983 (2)	0.0745 (11)
C18	−0.4058 (5)	0.39282 (13)	0.3700 (2)	0.0646 (10)
C19	1.8035 (5)	0.42227 (14)	1.0791 (2)	0.0716 (10)
C20	0.2392 (5)	0.26103 (12)	0.6752 (2)	0.0690 (10)
H2	0.94040	0.32360	0.85510	0.0700*
H2O	0.25380	0.46790	0.59560	0.1070*
H3	1.28940	0.30780	0.96930	0.0720*
H5	1.49530	0.47760	0.95970	0.0590*
H6	1.14600	0.49280	0.84550	0.0600*
H7	0.76850	0.46160	0.74540	0.0610*
H8	0.60180	0.34730	0.74450	0.0620*
H14	−0.54550	0.27420	0.47690	0.0650*
H15	−0.89240	0.27130	0.35690	0.0830*
H16	−0.93130	0.34320	0.24420	0.0950*
H17	−0.63050	0.41850	0.25290	0.0890*
H18	−0.28550	0.42380	0.37350	0.0770*
H19A	1.87980	0.43950	1.02860	0.1080*
H19B	1.94210	0.40600	1.12290	0.1080*
H19C	1.71030	0.45190	1.10880	0.1080*
H20A	0.14180	0.22520	0.66150	0.1040*
H20B	0.23990	0.27080	0.73920	0.1040*
H20C	0.41850	0.25590	0.66260	0.1040*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0690 (11)	0.0494 (10)	0.0744 (13)	−0.0022 (9)	−0.0138 (9)	0.0081 (9)
O2	0.0694 (11)	0.0573 (11)	0.0793 (14)	−0.0111 (9)	−0.0170 (10)	0.0090 (10)
O3	0.0580 (10)	0.0666 (12)	0.0776 (13)	−0.0102 (9)	−0.0174 (9)	0.0148 (10)
N1	0.0482 (10)	0.0453 (12)	0.0552 (13)	0.0029 (8)	−0.0083 (9)	0.0015 (9)
N2	0.0576 (11)	0.0460 (11)	0.0581 (13)	0.0010 (9)	−0.0075 (10)	0.0045 (10)
C1	0.0451 (11)	0.0504 (13)	0.0490 (14)	−0.0043 (10)	0.0021 (10)	−0.0069 (11)
C2	0.0532 (13)	0.0502 (14)	0.0680 (17)	−0.0098 (11)	−0.0042 (12)	−0.0042 (13)
C3	0.0554 (13)	0.0447 (13)	0.0749 (18)	−0.0041 (11)	−0.0053 (13)	0.0066 (13)
C4	0.0452 (12)	0.0557 (15)	0.0550 (15)	−0.0021 (11)	0.0012 (11)	0.0037 (12)
C5	0.0464 (12)	0.0465 (13)	0.0527 (14)	−0.0076 (10)	−0.0014 (10)	−0.0036 (11)
C6	0.0510 (11)	0.0453 (13)	0.0529 (15)	−0.0055 (10)	0.0005 (11)	0.0022 (11)
C7	0.0465 (13)	0.0520 (14)	0.0521 (15)	−0.0015 (10)	−0.0010 (10)	0.0000 (12)
C8	0.0477 (12)	0.0537 (15)	0.0529 (15)	−0.0022 (10)	0.0007 (11)	−0.0045 (11)
C9	0.0479 (12)	0.0563 (15)	0.0510 (15)	−0.0013 (10)	0.0038 (11)	−0.0039 (11)
C10	0.0428 (11)	0.0498 (13)	0.0483 (14)	0.0020 (10)	−0.0012 (10)	−0.0018 (11)
C11	0.0490 (12)	0.0469 (13)	0.0511 (14)	0.0014 (10)	−0.0038 (10)	−0.0008 (11)
C12	0.0505 (12)	0.0450 (14)	0.0550 (16)	0.0021 (10)	0.0003 (11)	0.0002 (11)
C13	0.0448 (12)	0.0528 (14)	0.0484 (14)	0.0112 (10)	−0.0027 (10)	−0.0070 (11)
C14	0.0518 (13)	0.0520 (14)	0.0560 (15)	0.0073 (11)	−0.0073 (11)	−0.0062 (12)
C15	0.0585 (14)	0.0662 (17)	0.075 (2)	0.0023 (12)	−0.0167 (13)	−0.0126 (15)
C16	0.0740 (18)	0.077 (2)	0.074 (2)	0.0172 (16)	−0.0334 (16)	−0.0075 (17)
C17	0.0805 (18)	0.072 (2)	0.0643 (19)	0.0138 (16)	−0.0156 (15)	0.0063 (15)
C18	0.0625 (16)	0.0652 (18)	0.0615 (17)	0.0041 (13)	−0.0082 (13)	0.0047 (14)
C19	0.0574 (14)	0.081 (2)	0.0697 (18)	−0.0097 (14)	−0.0168 (13)	0.0025 (16)
C20	0.0720 (17)	0.0543 (16)	0.0721 (18)	−0.0016 (13)	−0.0225 (14)	0.0081 (14)

Geometric parameters (Å, º) top

O1—C12	1.266 (3)	C13—C14	1.381 (3)
O2—C9	1.313 (3)	C14—C15	1.383 (4)
O3—C4	1.358 (3)	C15—C16	1.379 (4)
O3—C19	1.420 (3)	C16—C17	1.365 (5)
O2—H2O	0.8200	C17—C18	1.385 (4)
N1—N2	1.401 (3)	C2—H2	0.9300
N1—C13	1.419 (3)	C3—H3	0.9300
N1—C12	1.352 (3)	C5—H5	0.9300
N2—C11	1.307 (3)	C6—H6	0.9300
C1—C2	1.396 (4)	C7—H7	0.9300
C1—C7	1.453 (3)	C8—H8	0.9300
C1—C6	1.390 (3)	C14—H14	0.9300
C2—C3	1.373 (4)	C15—H15	0.9300
C3—C4	1.391 (4)	C16—H16	0.9300
C4—C5	1.380 (4)	C17—H17	0.9300
C5—C6	1.374 (3)	C18—H18	0.9300
C7—C8	1.331 (3)	C19—H19A	0.9600
C8—C9	1.440 (3)	C19—H19B	0.9600
C9—C10	1.387 (3)	C19—H19C	0.9600
C10—C11	1.434 (3)	C20—H20A	0.9600
C10—C12	1.430 (3)	C20—H20B	0.9600
C11—C20	1.482 (4)	C20—H20C	0.9600
C13—C18	1.386 (4)

C4—O3—C19	117.6 (2)	C16—C17—C18	121.4 (3)
C9—O2—H2O	109.00	C13—C18—C17	118.6 (3)
N2—N1—C12	111.33 (18)	C1—C2—H2	119.00
N2—N1—C13	118.97 (19)	C3—C2—H2	119.00
C12—N1—C13	129.6 (2)	C2—C3—H3	120.00
N1—N2—C11	106.58 (19)	C4—C3—H3	120.00
C2—C1—C6	117.3 (2)	C4—C5—H5	120.00
C6—C1—C7	119.6 (2)	C6—C5—H5	120.00
C2—C1—C7	123.1 (2)	C1—C6—H6	119.00
C1—C2—C3	121.1 (2)	C5—C6—H6	119.00
C2—C3—C4	120.2 (2)	C1—C7—H7	116.00
O3—C4—C3	115.2 (2)	C8—C7—H7	116.00
O3—C4—C5	124.9 (2)	C7—C8—H8	119.00
C3—C4—C5	119.9 (2)	C9—C8—H8	119.00
C4—C5—C6	119.1 (2)	C13—C14—H14	120.00
C1—C6—C5	122.4 (2)	C15—C14—H14	120.00
C1—C7—C8	128.7 (2)	C14—C15—H15	120.00
C7—C8—C9	122.8 (2)	C16—C15—H15	120.00
O2—C9—C8	116.3 (2)	C15—C16—H16	120.00
O2—C9—C10	117.9 (2)	C17—C16—H16	120.00
C8—C9—C10	125.8 (2)	C16—C17—H17	119.00
C9—C10—C11	136.0 (2)	C18—C17—H17	119.00
C9—C10—C12	119.5 (2)	C13—C18—H18	121.00
C11—C10—C12	104.56 (19)	C17—C18—H18	121.00
N2—C11—C20	119.0 (2)	O3—C19—H19A	110.00
C10—C11—C20	129.7 (2)	O3—C19—H19B	109.00
N2—C11—C10	111.2 (2)	O3—C19—H19C	109.00
O1—C12—N1	126.6 (2)	H19A—C19—H19B	109.00
N1—C12—C10	106.3 (2)	H19A—C19—H19C	109.00
O1—C12—C10	127.1 (2)	H19B—C19—H19C	109.00
N1—C13—C14	118.6 (2)	C11—C20—H20A	109.00
C14—C13—C18	120.6 (2)	C11—C20—H20B	109.00
N1—C13—C18	120.8 (2)	C11—C20—H20C	109.00
C13—C14—C15	119.5 (2)	H20A—C20—H20B	110.00
C14—C15—C16	120.3 (3)	H20A—C20—H20C	109.00
C15—C16—C17	119.6 (3)	H20B—C20—H20C	109.00

C19—O3—C4—C3	178.9 (2)	C4—C5—C6—C1	0.3 (4)
C19—O3—C4—C5	−2.2 (3)	C1—C7—C8—C9	179.2 (2)
C12—N1—N2—C11	−1.0 (3)	C7—C8—C9—C10	179.4 (2)
C13—N1—N2—C11	175.09 (19)	C7—C8—C9—O2	−0.1 (4)
N2—N1—C12—C10	0.6 (2)	O2—C9—C10—C11	−178.3 (3)
C13—N1—C12—C10	−174.9 (2)	C8—C9—C10—C12	−177.7 (2)
N2—N1—C13—C14	20.3 (3)	O2—C9—C10—C12	1.8 (3)
C12—N1—C13—C14	−164.5 (2)	C8—C9—C10—C11	2.3 (4)
N2—N1—C13—C18	−159.5 (2)	C12—C10—C11—C20	178.0 (2)
C12—N1—C13—C18	15.8 (4)	C9—C10—C12—O1	−0.5 (4)
N2—N1—C12—O1	−178.9 (2)	C9—C10—C12—N1	179.9 (2)
C13—N1—C12—O1	5.5 (4)	C11—C10—C12—O1	179.5 (2)
N1—N2—C11—C20	−177.8 (2)	C11—C10—C12—N1	−0.1 (2)
N1—N2—C11—C10	0.9 (3)	C9—C10—C11—N2	179.5 (3)
C7—C1—C2—C3	−179.2 (2)	C9—C10—C11—C20	−2.0 (5)
C2—C1—C6—C5	−0.8 (4)	C12—C10—C11—N2	−0.5 (3)
C6—C1—C2—C3	0.7 (4)	N1—C13—C14—C15	−179.5 (2)
C6—C1—C7—C8	−179.5 (2)	C18—C13—C14—C15	0.2 (4)
C2—C1—C7—C8	0.4 (4)	N1—C13—C18—C17	178.9 (2)
C7—C1—C6—C5	179.2 (2)	C14—C13—C18—C17	−0.8 (4)
C1—C2—C3—C4	−0.2 (4)	C13—C14—C15—C16	0.5 (4)
C2—C3—C4—C5	−0.3 (4)	C14—C15—C16—C17	−0.7 (4)
C2—C3—C4—O3	178.7 (2)	C15—C16—C17—C18	0.0 (5)
O3—C4—C5—C6	−178.7 (2)	C16—C17—C18—C13	0.7 (4)
C3—C4—C5—C6	0.2 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2O···O1	0.82	1.77	2.529 (3)	153
C7—H7···O2	0.93	2.37	2.743 (3)	104
C14—H14···N2	0.93	2.47	2.792 (3)	100
C18—H18···O1	0.93	2.36	2.947 (3)	121

Experimental details

Crystal data
Chemical formula	C₂₀H₁₈N₂O₃
M_r	334.36
Crystal system, space group	Monoclinic, Cc
Temperature (K)	296
a, b, c (Å)	5.0803 (2), 22.7645 (9), 14.5880 (6)
β (°)	97.626 (2)
V (Å³)	1672.19 (12)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.33 × 0.24 × 0.18

Data collection
Diffractometer	Bruker Kappa APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.971, 0.984
No. of measured, independent and observed [I > 2σ(I)] reflections	9137, 2056, 2628
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.666

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.094, 1.05
No. of reflections	2056
No. of parameters	229
No. of restraints	2
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.10, −0.16

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2O···O1	0.82	1.77	2.529 (3)	153

Acknowledgements

KIM acknowledges the Institute of Chemistry, University of the Punjab, for providing research facilities, and the Education Department, Government of the Punjab, for their co-operation.

References

Arshad, M. N., Tahir, M. N., Asghar, M. N., Khan, I. U. & Ashfaq, M. (2008). Acta Cryst. E64, o1413. Web of Science CSD CrossRef IUCr Journals Google Scholar
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573. CrossRef CAS Web of Science Google Scholar
Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. CrossRef CAS IUCr Journals Google Scholar
Konieczny, T. M., Konieczny, W., Sabisz, M., Skladanowski, A., Wakiec, R., Augustynowicz-Kopec, E. & Zwolska, Z. (2007). Eur. J. Med. Chem. 65, 729–733. Web of Science CrossRef Google Scholar
Mityurina1, K. V., Kulikova1, L. K., Krasheninnikova1, M. K., & Kharchenko1, V. G. (1981). Pharm. Chem. J. 15, 861–863. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 65| Part 12| December 2009| Page o3046

doi:10.1107/S1600536809046200

Open

access

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

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

(4Z)-4-[(2E)-1-Hydr­­oxy-3-(4-meth­oxy­phen­yl)prop-2-en­yl­idene]-3-methyl-1-phenyl-1H-pyrazol-5(4H)-one

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

(4Z)-4-[(2E)-1-Hydroxy-3-(4-methoxyphenyl)prop-2-enylidene]-3-methyl-1-phenyl-1H-pyrazol-5(4H)-one