Crystal structure of (4E)-4-(8-meth­oxy-2H-chromen-2-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/S2056989015009445

organic compounds

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ISSN: 2056-9890

Volume 71| Part 6| June 2015| Pages o414-o415

doi:10.1107/S2056989015009445

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Crystal structure of (4E)-4-(8-methoxy-2H-chromen-2-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. Imhof, University Koblenz-Landau, Germany (Received 6 May 2015; accepted 18 May 2015; online 23 May 2015)

In the title compound, C₂₀H₁₆N₂O₃, the phenyl substituent attached to the pyrazole ring makes a dihedral angle of 4.87 (7)° with the rest of the molecule. In the crystal, molecules are connected into inversion dimers of the R₂²(14) type by pairs of C—H⋯O interactions. π–π interactions exist between the benzene and pyrazole rings at a distance of 3.701 (1) Å. Similarly, π–π interactions are present at a centroid–centroid distance of 3.601 (1) Å between the oxygen-containing heterocyclic ring and methoxy substituted aromatic ring of a neighbouring molecule. Additional C—H⋯π and C=O⋯π interactions are also observed.

Keywords: crystal structure; pyrazolone; π–π interactions.

CCDC reference: 1401584

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

C₂₀H₁₆N₂O₃
M_r = 332.35
Monoclinic, C 2/c
a = 28.179 (5) Å
b = 4.7108 (8) Å
c = 23.819 (5) Å
β = 92.957 (7)°
V = 3157.7 (10) Å³
Z = 8
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 296 K
0.40 × 0.22 × 0.18 mm

2.2. Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.961, T_max = 0.985
13056 measured reflections
3419 independent reflections
2389 reflections with I > 2σ(I)
R_int = 0.033

2.3. Refinement

R[F² > 2σ(F²)] = 0.042
wR(F²) = 0.127
S = 1.06
3419 reflections
229 parameters
H-atom parameters constrained
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.16 e Å⁻³

Table 1
Hydrogen-bond geometry and C—H⋯π and C=O⋯π interactions (Å, °)

Cg1 and Cg2 are the centroids of the N1/N2/C7–C9 and C11–C14/C19/O2 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯O1	0.93	2.28	2.911 (2)	124
C12—H12⋯O1	0.93	2.38	3.004 (2)	124
C13—H13⋯O1ⁱ	0.93	2.53	3.2577 (19)	136
C10—H10A⋯Cg1ⁱⁱ	0.96	2.79	3.6812 (17)	155
C7—O1⋯Cg2ⁱⁱⁱ	1.23 (1)	3.65 (1)	3.9797 (18)	96 (1)
Symmetry codes: (i) -x, -y+2, -z; (ii) x, y-1, z; (iii) x, y+1, z.

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: 1401584

Crystal structure: contains datablocks global, I. DOI: 10.1107/S2056989015009445/im2465sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S2056989015009445/im2465Isup2.hkl

Supporting information file. DOI: 10.1107/S2056989015009445/im2465Isup3.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). No crystal structure has been found containing a 8-methoxy-2H-chromene subunit. (I) is synthesized for the biological studies etc.

In (I), the benzene ring A (C1–C6) and the (4E)-4-(8-methoxy-2H-chromen-2-ylidene)-5-methyl-2,4-dihydro-3H-pyrazol-3-one (C7 –C20/N1/N2/O1/O2/O3) part of the molecule are planar with r. m. s. deviations of 0.0053 and 0.0108 Å, respectively. The dihedral angle between A/B is 4.87 (7)°. The molecules are dimerized due to C—H···O interactions completing R₂² (14) Molecules are connected to inversion dimers dimerized of the R₂² (14) type by C—H···O interactions. There exist π–π interactions at a distance of 3.7011 (12) Å between the centeroids of Cg1—Cg3ⁱ and Cg3—Cg1ⁱⁱ [i = x, - 1 + y, z and ii = x, 1 + y, z], where Cg1 and Cg3 are the centroids of heterocyclic ring C (N1/N2/C7/C8/C9) and benzene ring A, respectively. Similarly, there exist π–π interaction at a distance of 3.6012 (11) Å between the centeroids of Cg2—Cg4ⁱⁱ and Cg4—Cg2ⁱ [i = x, - 1 + y, z and ii = x, 1 + y, z], where Cg2 and Cg4 are the centroids of heterocyclic ring D (C11—C14/C19/O2) and methoxy containing benzene ring E (C14—C19), respectively. There exist C—H···π and C=O···π interactions (Table 1).

Related literature top

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

Experimental top

For the preparation of title compound (I), a mixture of 4-acetyl-3-methyl-1-phenyl-5-hydroxy pyrazole (0.218 g, 1 mmoL), 2-methoxybenzaldehyde (0.205 g, 1.5 mmoL) was refluxed for 8 h in glacial acetic acid (15 ml) and concentrated sulfuric acid (0.2 ml). The reaction mixture was diluted with distilled water (60 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 using n-hexane to afford red needles (yield = 63%, m.p. 503 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 the atom numbering scheme. Thermal ellipsoids are drawn at the 50% probability level. H-atoms are shown by small circles of arbitrary radii.
	Fig. 2. Partial packing (PLATON; Spek, 2009) which shows that molecules are dimerized due to C—H···O bondings.

(4E)-4-(8-Methoxy-2H-chromen-2-ylidene)-3-methyl-1-phenyl-1H-pyrazol-5(4H)-one top

Crystal data top

C₂₀H₁₆N₂O₃	F(000) = 1392
M_r = 332.35	D_x = 1.398 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 28.179 (5) Å	Cell parameters from 2389 reflections
b = 4.7108 (8) Å	θ = 2.9–27.0°
c = 23.819 (5) Å	µ = 0.10 mm⁻¹
β = 92.957 (7)°	T = 296 K
V = 3157.7 (10) Å³	Needle, red
Z = 8	0.40 × 0.22 × 0.18 mm

Data collection top

Bruker Kappa APEXII CCD diffractometer	3419 independent reflections
Radiation source: fine-focus sealed tube	2389 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.033
Detector resolution: 7.70 pixels mm^-1	θ_max = 27.0°, θ_min = 2.9°
ω scans	h = −35→35
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −6→5
T_min = 0.961, T_max = 0.985	l = −24→30
13056 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)] = 0.042	H-atom parameters constrained
wR(F²) = 0.127	w = 1/[σ²(F_o²) + (0.0648P)² + 0.6123P] where P = (F_o² + 2F_c²)/3
S = 1.06	(Δ/σ)_max < 0.001
3419 reflections	Δρ_max = 0.22 e Å⁻³
229 parameters	Δρ_min = −0.16 e Å⁻³
0 restraints	Extinction correction: SHELXL2014 (Sheldrick, 2015), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0021 (4)

Crystal data top

C₂₀H₁₆N₂O₃	V = 3157.7 (10) Å³
M_r = 332.35	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 28.179 (5) Å	µ = 0.10 mm⁻¹
b = 4.7108 (8) Å	T = 296 K
c = 23.819 (5) Å	0.40 × 0.22 × 0.18 mm
β = 92.957 (7)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	3419 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	2389 reflections with I > 2σ(I)
T_min = 0.961, T_max = 0.985	R_int = 0.033
13056 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	0 restraints
wR(F²) = 0.127	H-atom parameters constrained
S = 1.06	Δρ_max = 0.22 e Å⁻³
3419 reflections	Δρ_min = −0.16 e Å⁻³
229 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	0.06562 (4)	1.0410 (2)	0.06364 (5)	0.0601 (4)
O2	0.11680 (3)	0.3975 (2)	−0.05229 (4)	0.0405 (3)
O3	0.16619 (4)	0.0352 (2)	−0.10799 (5)	0.0504 (3)
N1	0.14466 (4)	0.9876 (2)	0.09568 (5)	0.0407 (3)
N2	0.18451 (4)	0.8288 (2)	0.08158 (6)	0.0417 (3)
C1	0.14967 (6)	1.1800 (3)	0.14142 (6)	0.0410 (4)
C2	0.19424 (6)	1.2193 (3)	0.16813 (7)	0.0501 (4)
H2	0.2202	1.1180	0.1563	0.060*
C3	0.19992 (7)	1.4086 (4)	0.21225 (8)	0.0575 (5)
H3	0.2298	1.4329	0.2301	0.069*
C4	0.16197 (8)	1.5617 (4)	0.23019 (8)	0.0593 (5)
H4	0.1661	1.6913	0.2595	0.071*
C5	0.11808 (7)	1.5206 (4)	0.20427 (8)	0.0619 (5)
H5	0.0923	1.6222	0.2164	0.074*
C6	0.11134 (7)	1.3295 (3)	0.16006 (7)	0.0541 (5)
H6	0.0812	1.3025	0.1431	0.065*
C7	0.10494 (5)	0.9304 (3)	0.06052 (7)	0.0410 (4)
C8	0.12183 (5)	0.7169 (3)	0.02175 (6)	0.0372 (4)
C9	0.17098 (5)	0.6713 (3)	0.03861 (7)	0.0370 (4)
C10	0.20563 (5)	0.4738 (3)	0.01377 (7)	0.0451 (4)
H10A	0.1932	0.2840	0.0139	0.068*
H10B	0.2352	0.4800	0.0356	0.068*
H10C	0.2108	0.5304	−0.0242	0.068*
C11	0.09468 (5)	0.5939 (3)	−0.02107 (6)	0.0368 (4)
C12	0.04599 (5)	0.6554 (3)	−0.03528 (7)	0.0455 (4)
H12	0.0304	0.7917	−0.0149	0.055*
C13	0.02230 (6)	0.5199 (3)	−0.07759 (7)	0.0492 (4)
H13	−0.0096	0.5601	−0.0856	0.059*
C14	0.04580 (5)	0.3138 (3)	−0.11063 (7)	0.0435 (4)
C15	0.02414 (6)	0.1660 (4)	−0.15629 (8)	0.0562 (5)
H15	−0.0078	0.1959	−0.1664	0.067*
C16	0.05019 (7)	−0.0228 (4)	−0.18596 (8)	0.0583 (5)
H16	0.0357	−0.1184	−0.2164	0.070*
C17	0.09766 (6)	−0.0735 (3)	−0.17137 (7)	0.0490 (4)
H17	0.1146	−0.2024	−0.1921	0.059*
C18	0.12003 (5)	0.0664 (3)	−0.12619 (7)	0.0404 (4)
C19	0.09317 (5)	0.2600 (3)	−0.09639 (6)	0.0373 (4)
C20	0.19362 (6)	−0.1685 (4)	−0.13639 (8)	0.0533 (5)
H20A	0.1797	−0.3531	−0.1328	0.080*
H20B	0.2255	−0.1704	−0.1201	0.080*
H20C	0.1942	−0.1191	−0.1754	0.080*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0403 (7)	0.0647 (7)	0.0753 (9)	0.0165 (6)	0.0028 (6)	−0.0223 (7)
O2	0.0332 (6)	0.0421 (5)	0.0463 (7)	0.0051 (4)	0.0011 (5)	−0.0075 (5)
O3	0.0370 (6)	0.0583 (7)	0.0556 (7)	0.0076 (5)	0.0004 (5)	−0.0180 (6)
N1	0.0402 (7)	0.0393 (6)	0.0429 (8)	0.0073 (5)	0.0044 (6)	−0.0023 (6)
N2	0.0404 (8)	0.0400 (6)	0.0450 (8)	0.0098 (5)	0.0040 (6)	0.0006 (6)
C1	0.0522 (10)	0.0341 (7)	0.0372 (9)	0.0036 (6)	0.0069 (7)	0.0040 (7)
C2	0.0550 (11)	0.0476 (9)	0.0477 (10)	−0.0008 (7)	0.0044 (8)	−0.0021 (8)
C3	0.0697 (13)	0.0533 (10)	0.0496 (11)	−0.0105 (9)	0.0030 (9)	−0.0022 (9)
C4	0.0898 (16)	0.0451 (9)	0.0432 (11)	−0.0025 (9)	0.0052 (10)	−0.0037 (8)
C5	0.0816 (15)	0.0547 (10)	0.0501 (11)	0.0199 (9)	0.0104 (10)	−0.0039 (9)
C6	0.0592 (11)	0.0539 (9)	0.0491 (11)	0.0147 (8)	0.0022 (9)	−0.0044 (9)
C7	0.0380 (9)	0.0383 (7)	0.0472 (10)	0.0053 (6)	0.0059 (7)	0.0001 (7)
C8	0.0347 (8)	0.0346 (7)	0.0427 (9)	0.0040 (6)	0.0070 (7)	0.0010 (7)
C9	0.0369 (8)	0.0331 (7)	0.0413 (9)	0.0045 (6)	0.0063 (7)	0.0037 (7)
C10	0.0390 (9)	0.0433 (8)	0.0531 (10)	0.0080 (6)	0.0040 (7)	−0.0034 (7)
C11	0.0342 (8)	0.0340 (7)	0.0430 (9)	0.0046 (6)	0.0084 (7)	0.0028 (7)
C12	0.0368 (9)	0.0446 (8)	0.0554 (11)	0.0090 (7)	0.0066 (8)	0.0007 (8)
C13	0.0324 (9)	0.0537 (9)	0.0609 (11)	0.0080 (7)	−0.0020 (8)	0.0042 (8)
C14	0.0364 (9)	0.0443 (8)	0.0493 (10)	0.0028 (6)	−0.0020 (7)	0.0039 (7)
C15	0.0417 (10)	0.0619 (10)	0.0634 (12)	0.0029 (8)	−0.0131 (9)	0.0000 (9)
C16	0.0561 (11)	0.0632 (11)	0.0541 (12)	−0.0012 (9)	−0.0139 (9)	−0.0080 (9)
C17	0.0504 (10)	0.0507 (9)	0.0457 (10)	0.0016 (7)	0.0004 (8)	−0.0065 (8)
C18	0.0358 (9)	0.0419 (8)	0.0434 (9)	0.0002 (6)	0.0017 (7)	0.0006 (7)
C19	0.0366 (8)	0.0362 (7)	0.0388 (9)	−0.0014 (6)	0.0000 (7)	0.0013 (7)
C20	0.0453 (10)	0.0585 (10)	0.0565 (11)	0.0111 (8)	0.0060 (8)	−0.0096 (9)

Geometric parameters (Å, º) top

O1—C7	1.2299 (17)	C8—C9	1.438 (2)
O2—C11	1.3584 (17)	C9—C10	1.4931 (19)
O2—C19	1.3766 (17)	C10—H10A	0.9600
O3—C18	1.3578 (18)	C10—H10B	0.9600
O3—C20	1.4244 (18)	C10—H10C	0.9600
N1—C7	1.389 (2)	C11—C12	1.426 (2)
N1—N2	1.4046 (16)	C12—C13	1.341 (2)
N1—C1	1.419 (2)	C12—H12	0.9300
N2—C9	1.3048 (19)	C13—C14	1.433 (2)
C1—C6	1.382 (2)	C13—H13	0.9300
C1—C2	1.390 (2)	C14—C19	1.384 (2)
C2—C3	1.381 (2)	C14—C15	1.404 (2)
C2—H2	0.9300	C15—C16	1.372 (2)
C3—C4	1.376 (3)	C15—H15	0.9300
C3—H3	0.9300	C16—C17	1.385 (2)
C4—C5	1.367 (3)	C16—H16	0.9300
C4—H4	0.9300	C17—C18	1.385 (2)
C5—C6	1.391 (2)	C17—H17	0.9300
C5—H5	0.9300	C18—C19	1.401 (2)
C6—H6	0.9300	C20—H20A	0.9600
C7—C8	1.462 (2)	C20—H20B	0.9600
C8—C11	1.371 (2)	C20—H20C	0.9600

C11—O2—C19	121.38 (11)	C9—C10—H10C	109.5
C18—O3—C20	117.11 (12)	H10A—C10—H10C	109.5
C7—N1—N2	112.43 (12)	H10B—C10—H10C	109.5
C7—N1—C1	129.21 (13)	O2—C11—C8	116.14 (13)
N2—N1—C1	118.35 (12)	O2—C11—C12	118.14 (14)
C9—N2—N1	106.59 (12)	C8—C11—C12	125.72 (14)
C6—C1—C2	119.19 (15)	C13—C12—C11	121.15 (15)
C6—C1—N1	121.59 (15)	C13—C12—H12	119.4
C2—C1—N1	119.22 (14)	C11—C12—H12	119.4
C3—C2—C1	120.04 (16)	C12—C13—C14	120.59 (14)
C3—C2—H2	120.0	C12—C13—H13	119.7
C1—C2—H2	120.0	C14—C13—H13	119.7
C4—C3—C2	120.87 (18)	C19—C14—C15	118.31 (15)
C4—C3—H3	119.6	C19—C14—C13	117.17 (14)
C2—C3—H3	119.6	C15—C14—C13	124.52 (15)
C5—C4—C3	118.99 (17)	C16—C15—C14	119.84 (16)
C5—C4—H4	120.5	C16—C15—H15	120.1
C3—C4—H4	120.5	C14—C15—H15	120.1
C4—C5—C6	121.25 (18)	C15—C16—C17	121.19 (16)
C4—C5—H5	119.4	C15—C16—H16	119.4
C6—C5—H5	119.4	C17—C16—H16	119.4
C1—C6—C5	119.64 (18)	C16—C17—C18	120.50 (16)
C1—C6—H6	120.2	C16—C17—H17	119.7
C5—C6—H6	120.2	C18—C17—H17	119.7
O1—C7—N1	125.57 (15)	O3—C18—C17	125.90 (14)
O1—C7—C8	130.78 (15)	O3—C18—C19	116.25 (13)
N1—C7—C8	103.65 (12)	C17—C18—C19	117.84 (14)
C11—C8—C9	129.57 (13)	O2—C19—C14	121.56 (13)
C11—C8—C7	124.98 (13)	O2—C19—C18	116.12 (13)
C9—C8—C7	105.45 (13)	C14—C19—C18	122.31 (14)
N2—C9—C8	111.87 (13)	O3—C20—H20A	109.5
N2—C9—C10	119.63 (13)	O3—C20—H20B	109.5
C8—C9—C10	128.50 (14)	H20A—C20—H20B	109.5
C9—C10—H10A	109.5	O3—C20—H20C	109.5
C9—C10—H10B	109.5	H20A—C20—H20C	109.5
H10A—C10—H10B	109.5	H20B—C20—H20C	109.5

C7—N1—N2—C9	−0.36 (16)	C19—O2—C11—C12	−0.2 (2)
C1—N1—N2—C9	−179.67 (12)	C9—C8—C11—O2	0.7 (2)
C7—N1—C1—C6	5.1 (2)	C7—C8—C11—O2	−179.45 (13)
N2—N1—C1—C6	−175.68 (14)	C9—C8—C11—C12	−179.11 (15)
C7—N1—C1—C2	−174.84 (15)	C7—C8—C11—C12	0.8 (2)
N2—N1—C1—C2	4.3 (2)	O2—C11—C12—C13	1.2 (2)
C6—C1—C2—C3	−0.8 (2)	C8—C11—C12—C13	−179.03 (15)
N1—C1—C2—C3	179.12 (14)	C11—C12—C13—C14	−1.5 (2)
C1—C2—C3—C4	−0.4 (3)	C12—C13—C14—C19	0.8 (2)
C2—C3—C4—C5	1.1 (3)	C12—C13—C14—C15	−178.71 (16)
C3—C4—C5—C6	−0.6 (3)	C19—C14—C15—C16	−1.0 (3)
C2—C1—C6—C5	1.4 (2)	C13—C14—C15—C16	178.53 (16)
N1—C1—C6—C5	−178.61 (14)	C14—C15—C16—C17	0.7 (3)
C4—C5—C6—C1	−0.7 (3)	C15—C16—C17—C18	0.0 (3)
N2—N1—C7—O1	−179.78 (15)	C20—O3—C18—C17	−2.8 (2)
C1—N1—C7—O1	−0.6 (3)	C20—O3—C18—C19	177.68 (14)
N2—N1—C7—C8	0.35 (16)	C16—C17—C18—O3	−179.84 (15)
C1—N1—C7—C8	179.58 (13)	C16—C17—C18—C19	−0.3 (2)
O1—C7—C8—C11	0.0 (3)	C11—O2—C19—C14	−0.5 (2)
N1—C7—C8—C11	179.86 (14)	C11—O2—C19—C18	178.69 (12)
O1—C7—C8—C9	179.92 (17)	C15—C14—C19—O2	179.76 (14)
N1—C7—C8—C9	−0.22 (15)	C13—C14—C19—O2	0.2 (2)
N1—N2—C9—C8	0.20 (16)	C15—C14—C19—C18	0.6 (2)
N1—N2—C9—C10	−179.44 (12)	C13—C14—C19—C18	−178.94 (14)
C11—C8—C9—N2	179.93 (14)	O3—C18—C19—O2	0.4 (2)
C7—C8—C9—N2	0.02 (17)	C17—C18—C19—O2	−179.14 (13)
C11—C8—C9—C10	−0.5 (3)	O3—C18—C19—C14	179.59 (14)
C7—C8—C9—C10	179.61 (14)	C17—C18—C19—C14	0.0 (2)
C19—O2—C11—C8	−179.97 (12)

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of the N1/N2/C7–C9 and C11–C14/C19/O2 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O1	0.93	2.28	2.911 (2)	124
C12—H12···O1	0.93	2.38	3.004 (2)	124
C13—H13···O1ⁱ	0.93	2.53	3.2577 (19)	136
C10—H10A···Cg1ⁱⁱ	0.96	2.79	3.6812 (17)	155
C7—O1···Cg2ⁱⁱⁱ	1.23 (1)	3.65 (1)	3.9797 (18)	96 (1)

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

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of the N1/N2/C7–C9 and C11–C14/C19/O2 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O1	0.93	2.28	2.911 (2)	124.4
C12—H12···O1	0.93	2.38	3.004 (2)	124.2
C13—H13···O1ⁱ	0.93	2.53	3.2577 (19)	135.9
C10—H10A···Cg1ⁱⁱ	0.96	2.79	3.6812 (17)	155
C7—O1···Cg2ⁱⁱⁱ	1.2299 (17)	3.6544 (15)	3.9797 (18)	96.2 (1)

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

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 o414-o415

doi:10.1107/S2056989015009445

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

Crystal structure of (4E)-4-(8-meth­­oxy-2H-chromen-2-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 (4E)-4-(8-methoxy-2H-chromen-2-ylidene)-3-methyl-1-phenyl-1H-pyrazol-5(4H)-one