Crystal structure of (4E)-4-(8-meth-oxy-2H-chromen-2-yl-idene)-3-methyl-1-phenyl-1H-pyrazol-5(4H)-one.

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 mol-ecule. In the crystal, mol-ecules are connected into inversion dimers of the R 2 (2)(14) type by pairs of C-H⋯O inter-actions. π-π inter-actions exist between the benzene and pyrazole rings at a distance of 3.701 (1) Å. Similarly, π-π inter-actions are present at a centroid-centroid distance of 3.601 (1) Å between the oxygen-containing heterocyclic ring and meth-oxy substituted aromatic ring of a neighbouring mol-ecule. Additional C-H⋯π and C=O⋯π inter-actions are also observed.

Related literature

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

Experimental

Crystal data

C20H16N2O3

M = 332.35

Monoclinic,

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

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

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.127

S = 1.06

3419 reflections

229 parameters

H-atom parameters constrained

Δρmax = 0.22 e Å−3

Δρmin = −0.16 e Å−3

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/S2056989015009445/im2465sup1.cif

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

Click here for additional data file.

Supporting information file. DOI: 10.1107/S2056989015009445/im2465Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S2056989015009445/im2465fig1.tif

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.

Click here for additional data file.

PLATON . DOI: 10.1107/S2056989015009445/im2465fig2.tif

Partial packing (PLATON; Spek, 2009) which shows that mol­ecules are dimerized due to C—H⋯O bondings.

CCDC reference: 1401584

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

C20H16N2O3	F(000) = 1392
Mr = 332.35	Dx = 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

Bruker Kappa APEXII CCD diffractometer	3419 independent reflections
Radiation source: fine-focus sealed tube	2389 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.033
Detector resolution: 7.70 pixels mm-1	θmax = 27.0°, θmin = 2.9°
ω scans	h = −35→35
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −6→5
Tmin = 0.961, Tmax = 0.985	l = −24→30
13056 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)] = 0.042	H-atom parameters constrained
wR(F2) = 0.127	w = 1/[σ2(Fo2) + (0.0648P)2 + 0.6123P] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max < 0.001
3419 reflections	Δρmax = 0.22 e Å−3
229 parameters	Δρmin = −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)

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
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*

	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)

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)

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)

Table 1

Hydrogen-bond geometry and CH and CO interactions (, )

Cg1 and Cg2 are the centroids of the N1/N2/C7C9 and C11C14/C19/O2 rings, respectively.

DHA	DH	HA	D A	DHA
C6H6O1	0.93	2.28	2.911(2)	124
C12H12O1	0.93	2.38	3.004(2)	124
C13H13O1i	0.93	2.53	3.2577(19)	136
C10H10A Cg1ii	0.96	2.79	3.6812(17)	155
C7O1Cg2iii	1.23(1)	3.65(1)	3.9797(18)	96(1)

Symmetry codes: (i) ; (ii) ; (iii) .