Crystal structure of (4Z)-4-[(2E)-1-hydroxy-3-(naphthalen-2-yl)prop-2-en-1-yl­idene]-3-methyl-1-phenyl-1H-pyrazol-5(4H)-one

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

doi:10.1107/S205698901500866X

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 71| Part 6| June 2015| Page o381

doi:10.1107/S205698901500866X

Open

access

Crystal structure of (4Z)-4-[(2E)-1-hydroxy-3-(naphthalen-2-yl)prop-2-en-1-ylidene]-3-methyl-1-phenyl-1H-pyrazol-5(4H)-one

Muhammad Salim,^a Munawar Ali Munawar,^a Muhammad Nawaz Tahir,^b ^* Muhammad Shahid ^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 4 May 2015; accepted 4 May 2015; online 9 May 2015)

In the title compound, C₂₃H₁₈N₂O₂, the pyrazole ring subtends dihedral angles of 2.01 (13) and 1.55 (10)° with the pendant benzene ring and the naphthalene ring system, respectively. The molecule is almost planar (r.m.s. deviation for the 27 non-H atoms = 0.025 Å) and intramolecular O—H⋯O and C—H⋯O hydrogen bonds both close S(6) loops. In the crystal, very weak aromatic π–π stacking interactions between the benzene and the pyrazole rings, with centroid–centroid distances of 3.8913 (14) and 3.9285 (15) Å, are observed.

Keywords: crystal structure; pyrazole; intramolecular hydrogen bonding; π–π stacking.

CCDC reference: 1062997

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

C₂₃H₁₈N₂O₂
M_r = 354.39
Monoclinic, P 2₁ /n
a = 6.7067 (8) Å
b = 17.525 (2) Å
c = 15.784 (2) Å
β = 101.152 (6)°
V = 1820.1 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 296 K
0.40 × 0.16 × 0.14 mm

2.2. Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.968, T_max = 0.986
13979 measured reflections
3574 independent reflections
1855 reflections with I > 2σ(I)
R_int = 0.055

2.3. Refinement

R[F² > 2σ(F²)] = 0.056
wR(F²) = 0.140
S = 0.99
3574 reflections
246 parameters
H-atom parameters constrained
Δρ_max = 0.13 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—H2A⋯O1	0.82	1.80	2.555 (2)	153
C6—H6⋯O1	0.93	2.30	2.940 (3)	126

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: 1062997

Crystal structure: contains datablocks global, I. DOI: 10.1107/S205698901500866X/hb7418sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S205698901500866X/hb7418Isup2.hkl

Supporting information file. DOI: 10.1107/S205698901500866X/hb7418Isup3.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 (4Z)-4-[(2E)-1- hydroxy-3-(naphthalen-2-yl)prop-2-en-1-ylidene]-5-methyl-2,4-dihydro-3H -pyrazol-3-one moiety B (C7 –C23/N1/N2/O1/O2) are almost planar with r.m.s. deviations of 0.0022 and 0.0179 Å, respectively. The dihedral angle between A/B is 2.30 (13)°. There exist intramolecular H-bonding of O—H···O type completing S (6) loop. There exist π–π interactions at a distance of 3.9285 (15) Å between the centroids 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 benzene ring A (Fig. 2). Similarly, there exist π–π interactions at a distance of 3.8913 (14) Å between the centroids of Cg3—Cg1ⁱ and Cg1— Cg3ⁱⁱ [i = 1 + x, y, z and ii = -1 + x, y, z], where Cg3 is the centroids of ring D (C14/C15/C16/C17/C22/C23).

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-hydroxy pyrazole (0.218 g, 1 mmol), 2-naphthaldehyde (0.234 g, 1.5 mmol) in glacial acetic acid (10 ml) and concentrated sulfuric acid (0.2 ml) was stirred at 353–360 K for 8 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 form n-hexane solution to afford purple needle. Yield = 56%, m.p. = 491 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, showing π–π interactions.

(4Z)-4-[(2E)-1-Hydroxy-3-(naphthalen-2-yl)prop-2-en-1-ylidene]-3-methyl-1-phenyl-1H-pyrazol-5(4H)-one top

Crystal data top

C₂₃H₁₈N₂O₂	F(000) = 744
M_r = 354.39	D_x = 1.293 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
a = 6.7067 (8) Å	Cell parameters from 1855 reflections
b = 17.525 (2) Å	θ = 2.6–26.0°
c = 15.784 (2) Å	µ = 0.08 mm⁻¹
β = 101.152 (6)°	T = 296 K
V = 1820.1 (4) Å³	Needle, purple
Z = 4	0.40 × 0.16 × 0.14 mm

Data collection top

Bruker Kappa APEXII CCD diffractometer	3574 independent reflections
Radiation source: fine-focus sealed tube	1855 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.055
Detector resolution: 7.80 pixels mm^-1	θ_max = 26.0°, θ_min = 2.6°
ω scans	h = −8→5
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −21→21
T_min = 0.968, T_max = 0.986	l = −19→19
13979 measured reflections

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)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.140	H-atom parameters constrained
S = 0.99	w = 1/[σ²(F_o²) + (0.0552P)²] where P = (F_o² + 2F_c²)/3
3574 reflections	(Δ/σ)_max < 0.001
246 parameters	Δρ_max = 0.13 e Å⁻³
0 restraints	Δρ_min = −0.16 e Å⁻³

Crystal data top

C₂₃H₁₈N₂O₂	V = 1820.1 (4) Å³
M_r = 354.39	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 6.7067 (8) Å	µ = 0.08 mm⁻¹
b = 17.525 (2) Å	T = 296 K
c = 15.784 (2) Å	0.40 × 0.16 × 0.14 mm
β = 101.152 (6)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	3574 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	1855 reflections with I > 2σ(I)
T_min = 0.968, T_max = 0.986	R_int = 0.055
13979 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.056	0 restraints
wR(F²) = 0.140	H-atom parameters constrained
S = 0.99	Δρ_max = 0.13 e Å⁻³
3574 reflections	Δρ_min = −0.16 e Å⁻³
246 parameters

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
O1	0.1673 (2)	0.54343 (9)	0.17724 (11)	0.0684 (5)
O2	0.4599 (3)	0.49546 (9)	0.10912 (11)	0.0672 (5)
H2A	0.3651	0.5215	0.1186	0.101*
N1	0.1223 (3)	0.46669 (10)	0.29460 (12)	0.0527 (5)
N2	0.2155 (3)	0.40098 (11)	0.33743 (12)	0.0593 (6)
C1	−0.0446 (3)	0.49941 (13)	0.32414 (15)	0.0510 (6)
C2	−0.1094 (4)	0.46827 (15)	0.39423 (17)	0.0714 (8)
H2	−0.0430	0.4260	0.4221	0.086*
C3	−0.2734 (4)	0.49985 (18)	0.42332 (19)	0.0851 (9)
H3	−0.3152	0.4788	0.4711	0.102*
C4	−0.3740 (4)	0.56112 (17)	0.3831 (2)	0.0800 (8)
H4	−0.4843	0.5818	0.4028	0.096*
C5	−0.3108 (4)	0.59203 (15)	0.3130 (2)	0.0764 (8)
H5	−0.3794	0.6339	0.2851	0.092*
C6	−0.1459 (4)	0.56188 (14)	0.28280 (16)	0.0639 (7)
H6	−0.1040	0.5835	0.2353	0.077*
C7	0.2133 (3)	0.48753 (12)	0.22764 (15)	0.0508 (6)
C8	0.3725 (3)	0.43280 (12)	0.22720 (14)	0.0462 (6)
C9	0.3620 (3)	0.38203 (12)	0.29714 (15)	0.0533 (6)
C10	0.4899 (4)	0.31336 (14)	0.32827 (16)	0.0743 (8)
H10A	0.4788	0.2767	0.2824	0.111*
H10B	0.4434	0.2910	0.3764	0.111*
H10C	0.6293	0.3286	0.3458	0.111*
C11	0.4960 (3)	0.43911 (13)	0.16670 (15)	0.0503 (6)
C12	0.6639 (3)	0.38941 (12)	0.15888 (15)	0.0535 (6)
H12	0.6932	0.3489	0.1974	0.064*
C13	0.7796 (3)	0.39858 (13)	0.09910 (15)	0.0532 (6)
H13	0.7481	0.4397	0.0617	0.064*
C14	0.9479 (3)	0.35123 (12)	0.08677 (15)	0.0490 (6)
C15	1.0124 (4)	0.28705 (13)	0.13931 (16)	0.0590 (7)
H15	0.9461	0.2750	0.1841	0.071*
C16	1.1694 (4)	0.24273 (13)	0.12549 (17)	0.0607 (7)
H16	1.2071	0.2005	0.1606	0.073*
C17	1.2762 (3)	0.25934 (13)	0.05903 (16)	0.0519 (6)
C18	1.4400 (4)	0.21453 (14)	0.04322 (18)	0.0667 (7)
H18	1.4792	0.1716	0.0771	0.080*
C19	1.5422 (4)	0.23311 (16)	−0.02099 (19)	0.0730 (8)
H19	1.6492	0.2028	−0.0308	0.088*
C20	1.4857 (4)	0.29768 (17)	−0.07192 (18)	0.0735 (8)
H20	1.5571	0.3104	−0.1149	0.088*
C21	1.3268 (4)	0.34231 (15)	−0.05928 (16)	0.0632 (7)
H21	1.2905	0.3849	−0.0939	0.076*
C22	1.2170 (3)	0.32398 (13)	0.00630 (14)	0.0491 (6)
C23	1.0518 (3)	0.36872 (13)	0.02178 (14)	0.0518 (6)
H23	1.0121	0.4111	−0.0128	0.062*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0733 (12)	0.0593 (11)	0.0730 (12)	0.0127 (9)	0.0152 (9)	0.0219 (9)
O2	0.0714 (14)	0.0630 (12)	0.0694 (12)	0.0042 (9)	0.0190 (9)	0.0172 (10)
N1	0.0513 (13)	0.0557 (12)	0.0505 (12)	0.0075 (10)	0.0082 (10)	0.0075 (10)
N2	0.0575 (14)	0.0632 (13)	0.0577 (13)	0.0130 (11)	0.0125 (10)	0.0150 (11)
C1	0.0440 (16)	0.0540 (15)	0.0523 (15)	0.0045 (12)	0.0028 (11)	−0.0076 (12)
C2	0.066 (2)	0.0815 (19)	0.0692 (19)	0.0154 (16)	0.0189 (15)	0.0112 (16)
C3	0.079 (2)	0.103 (2)	0.079 (2)	0.0145 (19)	0.0293 (17)	0.0075 (18)
C4	0.067 (2)	0.086 (2)	0.089 (2)	0.0127 (18)	0.0177 (17)	−0.0186 (19)
C5	0.073 (2)	0.0635 (18)	0.088 (2)	0.0187 (15)	0.0044 (16)	−0.0115 (17)
C6	0.0651 (18)	0.0612 (16)	0.0645 (17)	0.0099 (14)	0.0105 (13)	−0.0034 (14)
C7	0.0488 (16)	0.0475 (14)	0.0535 (15)	−0.0038 (12)	0.0029 (12)	0.0040 (12)
C8	0.0389 (14)	0.0490 (14)	0.0491 (14)	−0.0021 (12)	0.0051 (11)	0.0045 (11)
C9	0.0494 (16)	0.0521 (14)	0.0568 (15)	0.0034 (12)	0.0065 (12)	0.0079 (13)
C10	0.0706 (19)	0.0756 (18)	0.0787 (19)	0.0235 (15)	0.0194 (14)	0.0298 (15)
C11	0.0480 (16)	0.0451 (14)	0.0533 (15)	−0.0085 (12)	−0.0013 (12)	0.0003 (12)
C12	0.0501 (16)	0.0504 (14)	0.0584 (16)	−0.0051 (13)	0.0064 (12)	0.0034 (12)
C13	0.0521 (16)	0.0483 (14)	0.0581 (16)	−0.0096 (12)	0.0081 (12)	0.0002 (12)
C14	0.0445 (15)	0.0464 (14)	0.0552 (15)	−0.0089 (12)	0.0076 (12)	−0.0017 (12)
C15	0.0578 (17)	0.0536 (15)	0.0682 (17)	−0.0082 (13)	0.0185 (13)	0.0080 (13)
C16	0.0576 (17)	0.0504 (15)	0.0726 (18)	−0.0062 (14)	0.0088 (13)	0.0127 (13)
C17	0.0431 (15)	0.0480 (14)	0.0632 (17)	−0.0093 (12)	0.0070 (12)	−0.0082 (12)
C18	0.0623 (19)	0.0541 (16)	0.082 (2)	−0.0060 (14)	0.0104 (15)	−0.0042 (14)
C19	0.0643 (19)	0.0697 (19)	0.087 (2)	−0.0030 (15)	0.0187 (16)	−0.0200 (17)
C20	0.070 (2)	0.089 (2)	0.0660 (19)	−0.0130 (17)	0.0261 (15)	−0.0147 (17)
C21	0.0609 (18)	0.0693 (17)	0.0593 (17)	−0.0065 (15)	0.0113 (13)	−0.0028 (14)
C22	0.0466 (16)	0.0519 (15)	0.0475 (14)	−0.0113 (13)	0.0057 (11)	−0.0056 (12)
C23	0.0496 (16)	0.0482 (14)	0.0554 (16)	−0.0064 (12)	0.0042 (12)	0.0039 (12)

Geometric parameters (Å, º) top

O1—C7	1.262 (2)	C10—H10C	0.9600
O2—C11	1.332 (2)	C11—C12	1.447 (3)
O2—H2A	0.8200	C12—C13	1.342 (3)
N1—C7	1.368 (3)	C12—H12	0.9300
N1—C1	1.415 (3)	C13—C14	1.444 (3)
N1—N2	1.418 (2)	C13—H13	0.9300
N2—C9	1.312 (3)	C14—C23	1.381 (3)
C1—C2	1.377 (3)	C14—C15	1.414 (3)
C1—C6	1.383 (3)	C15—C16	1.360 (3)
C2—C3	1.387 (3)	C15—H15	0.9300
C2—H2	0.9300	C16—C17	1.410 (3)
C3—C4	1.359 (4)	C16—H16	0.9300
C3—H3	0.9300	C17—C18	1.412 (3)
C4—C5	1.371 (4)	C17—C22	1.416 (3)
C4—H4	0.9300	C18—C19	1.368 (3)
C5—C6	1.390 (3)	C18—H18	0.9300
C5—H5	0.9300	C19—C20	1.397 (3)
C6—H6	0.9300	C19—H19	0.9300
C7—C8	1.436 (3)	C20—C21	1.368 (3)
C8—C11	1.385 (3)	C20—H20	0.9300
C8—C9	1.430 (3)	C21—C22	1.418 (3)
C9—C10	1.504 (3)	C21—H21	0.9300
C10—H10A	0.9600	C22—C23	1.417 (3)
C10—H10B	0.9600	C23—H23	0.9300

C11—O2—H2A	109.5	O2—C11—C12	115.5 (2)
C7—N1—C1	130.2 (2)	C8—C11—C12	126.1 (2)
C7—N1—N2	111.32 (18)	C13—C12—C11	123.6 (2)
C1—N1—N2	118.43 (19)	C13—C12—H12	118.2
C9—N2—N1	106.08 (18)	C11—C12—H12	118.2
C2—C1—C6	119.4 (2)	C12—C13—C14	126.8 (2)
C2—C1—N1	119.8 (2)	C12—C13—H13	116.6
C6—C1—N1	120.8 (2)	C14—C13—H13	116.6
C1—C2—C3	120.1 (3)	C23—C14—C15	118.1 (2)
C1—C2—H2	119.9	C23—C14—C13	119.5 (2)
C3—C2—H2	119.9	C15—C14—C13	122.4 (2)
C4—C3—C2	121.0 (3)	C16—C15—C14	121.2 (2)
C4—C3—H3	119.5	C16—C15—H15	119.4
C2—C3—H3	119.5	C14—C15—H15	119.4
C3—C4—C5	119.1 (3)	C15—C16—C17	121.5 (2)
C3—C4—H4	120.4	C15—C16—H16	119.3
C5—C4—H4	120.4	C17—C16—H16	119.3
C4—C5—C6	121.1 (3)	C16—C17—C18	122.8 (2)
C4—C5—H5	119.4	C16—C17—C22	118.5 (2)
C6—C5—H5	119.4	C18—C17—C22	118.7 (2)
C1—C6—C5	119.3 (3)	C19—C18—C17	121.1 (3)
C1—C6—H6	120.3	C19—C18—H18	119.4
C5—C6—H6	120.3	C17—C18—H18	119.4
O1—C7—N1	127.1 (2)	C18—C19—C20	120.0 (3)
O1—C7—C8	127.3 (2)	C18—C19—H19	120.0
N1—C7—C8	105.57 (19)	C20—C19—H19	120.0
C11—C8—C9	135.0 (2)	C21—C20—C19	120.8 (3)
C11—C8—C7	119.6 (2)	C21—C20—H20	119.6
C9—C8—C7	105.3 (2)	C19—C20—H20	119.6
N2—C9—C8	111.71 (19)	C20—C21—C22	120.4 (2)
N2—C9—C10	118.5 (2)	C20—C21—H21	119.8
C8—C9—C10	129.8 (2)	C22—C21—H21	119.8
C9—C10—H10A	109.5	C17—C22—C23	118.8 (2)
C9—C10—H10B	109.5	C17—C22—C21	118.9 (2)
H10A—C10—H10B	109.5	C23—C22—C21	122.3 (2)
C9—C10—H10C	109.5	C14—C23—C22	121.9 (2)
H10A—C10—H10C	109.5	C14—C23—H23	119.0
H10B—C10—H10C	109.5	C22—C23—H23	119.0
O2—C11—C8	118.4 (2)

C7—N1—N2—C9	0.1 (2)	C7—C8—C11—O2	−1.4 (3)
C1—N1—N2—C9	179.18 (19)	C9—C8—C11—C12	0.3 (4)
C7—N1—C1—C2	−179.6 (2)	C7—C8—C11—C12	178.99 (19)
N2—N1—C1—C2	1.5 (3)	O2—C11—C12—C13	0.8 (3)
C7—N1—C1—C6	1.2 (4)	C8—C11—C12—C13	−179.6 (2)
N2—N1—C1—C6	−177.66 (19)	C11—C12—C13—C14	−179.44 (19)
C6—C1—C2—C3	−0.6 (4)	C12—C13—C14—C23	−180.0 (2)
N1—C1—C2—C3	−179.7 (2)	C12—C13—C14—C15	−0.2 (4)
C1—C2—C3—C4	0.7 (4)	C23—C14—C15—C16	−1.3 (3)
C2—C3—C4—C5	−0.3 (4)	C13—C14—C15—C16	179.0 (2)
C3—C4—C5—C6	−0.2 (4)	C14—C15—C16—C17	0.8 (4)
C2—C1—C6—C5	0.1 (3)	C15—C16—C17—C18	179.8 (2)
N1—C1—C6—C5	179.3 (2)	C15—C16—C17—C22	0.2 (3)
C4—C5—C6—C1	0.3 (4)	C16—C17—C18—C19	−178.9 (2)
C1—N1—C7—O1	1.4 (4)	C22—C17—C18—C19	0.7 (3)
N2—N1—C7—O1	−179.63 (19)	C17—C18—C19—C20	0.4 (4)
C1—N1—C7—C8	−178.9 (2)	C18—C19—C20—C21	−1.0 (4)
N2—N1—C7—C8	0.0 (2)	C19—C20—C21—C22	0.4 (4)
O1—C7—C8—C11	0.5 (3)	C16—C17—C22—C23	−0.7 (3)
N1—C7—C8—C11	−179.13 (19)	C18—C17—C22—C23	179.63 (19)
O1—C7—C8—C9	179.5 (2)	C16—C17—C22—C21	178.4 (2)
N1—C7—C8—C9	−0.1 (2)	C18—C17—C22—C21	−1.3 (3)
N1—N2—C9—C8	−0.2 (2)	C20—C21—C22—C17	0.7 (3)
N1—N2—C9—C10	−179.94 (18)	C20—C21—C22—C23	179.8 (2)
C11—C8—C9—N2	179.0 (2)	C15—C14—C23—C22	0.7 (3)
C7—C8—C9—N2	0.2 (3)	C13—C14—C23—C22	−179.51 (18)
C11—C8—C9—C10	−1.3 (4)	C17—C22—C23—C14	0.2 (3)
C7—C8—C9—C10	179.9 (2)	C21—C22—C23—C14	−178.8 (2)
C9—C8—C11—O2	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	1.80	2.555 (2)	153
C6—H6···O1	0.93	2.30	2.940 (3)	126

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2A···O1	0.82	1.80	2.555 (2)	153
C6—H6···O1	0.93	2.30	2.940 (3)	126

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

Bruker (2005). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Chaudhry, F., Tahir, M. N., Khan, M. A., Ather, A. Q. & Asif, N. (2012). Acta Cryst. E68, o2044. CSD CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Holzer, W., Mereiter, K. & Plagens, B. (1999). Heterocycles, 50, 799–818. CrossRef CAS Google Scholar
Malik, K. I., Munawar, M. A., Khan, M. A., Nadeem, S. & Mukhtar-ul-Hassan (2009). Acta Cryst. E65, o3046. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2015). Acta Cryst. C71, 3–8. Web of Science CrossRef 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 71| Part 6| June 2015| Page o381

doi:10.1107/S205698901500866X

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

Crystal structure of (4Z)-4-[(2E)-1-hy­droxy-3-(naphthalen-2-yl)prop-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)-1-hydroxy-3-(naphthalen-2-yl)prop-2-en-1-ylidene]-3-methyl-1-phenyl-1H-pyrazol-5(4H)-one