(4Z)-4-[(2E)-1-Hy-droxy-3-(3-nitro-phen-yl)prop-2-en-1-yl-idene]-3-methyl-1-(4-methyl-phen-yl)-1H-pyrazol-5(4H)-one.

In the title compound, C(20)H(17)N(3)O(4), the dihedral angles between the heterocyclic ring and the toluene and nitro-benzene rings are 4.21 (15) and 11.43 (14)°, respectively. The whole mol-ecule is close to planar (r.m.s. deviation for the 27 non-H atoms = 0.171 Å). Two S(6) rings are formed due to intra-molecular C-H⋯O and O-H⋯O hydrogen bonds. In the crystal, inversion dimers linked by pairs of C-H⋯O bonds generate R(2) (2)(10) loops and further C-H⋯O bonds link the dimers along the b-axis direction. There exist π-π inter-actions between the heterocyclic rings at a centroid-centroid distance of 3.7126 (10) Å and between the centroids of the benzene rings at a distance of 3.8710 (16) Å.

Related literature

For background and a related structure, see: Mukhtar et al. (2010 ▶). For other related structures, see: Udaya Lakshmi et al. (2005 ▶); Jadeja & Shah (2007 ▶).

Experimental

Crystal data

C20H17N3O4

M = 363.37

Monoclinic,

a = 19.8712 (16) Å

b = 12.1917 (10) Å

c = 16.733 (2) Å

β = 121.188 (4)°

V = 3467.9 (6) Å3

Z = 8

Mo Kα radiation

μ = 0.10 mm−1

T = 296 K

0.35 × 0.18 × 0.17 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.972, T max = 0.983

12231 measured reflections

3328 independent reflections

1823 reflections with I > 2σ(I)

R int = 0.039

Refinement

R[F 2 > 2σ(F 2)] = 0.052

wR(F 2) = 0.143

S = 1.02

3328 reflections

247 parameters

H-atom parameters constrained

Δρmax = 0.16 e Å−3

Δρmin = −0.22 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812025238/hb6835sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812025238/hb6835Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812025238/hb6835Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C20H17N3O4	F(000) = 1520
Mr = 363.37	Dx = 1.390 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 1823 reflections
a = 19.8712 (16) Å	θ = 2.1–26.0°
b = 12.1917 (10) Å	µ = 0.10 mm−1
c = 16.733 (2) Å	T = 296 K
β = 121.188 (4)°	Rod, orange
V = 3467.9 (6) Å3	0.35 × 0.18 × 0.17 mm
Z = 8

Bruker Kappa APEXII CCD diffractometer	3328 independent reflections
Radiation source: fine-focus sealed tube	1823 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.039
Detector resolution: 8.00 pixels mm-1	θmax = 26.0°, θmin = 2.1°
ω scans	h = −22→24
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −15→15
Tmin = 0.972, Tmax = 0.983	l = −20→13
12231 measured reflections

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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.143	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0688P)2] where P = (Fo2 + 2Fc2)/3
3328 reflections	(Δ/σ)max < 0.001
247 parameters	Δρmax = 0.16 e Å−3
0 restraints	Δρmin = −0.22 e Å−3

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 e.s.d.'s 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 > 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	−0.08035 (9)	0.17748 (13)	0.26833 (13)	0.0730 (6)
O2	0.04784 (9)	0.17674 (14)	0.42872 (13)	0.0821 (7)
O3	0.36766 (10)	0.22769 (14)	0.89614 (12)	0.0776 (7)
O4	0.45928 (10)	0.10845 (15)	0.95844 (14)	0.0945 (8)
N1	−0.12499 (10)	−0.00138 (14)	0.21735 (13)	0.0471 (6)
N2	−0.09808 (10)	−0.10774 (14)	0.24985 (14)	0.0569 (7)
N3	0.39439 (11)	0.13844 (17)	0.89657 (14)	0.0581 (8)
C1	−0.19601 (12)	0.01116 (18)	0.12989 (15)	0.0455 (8)
C2	−0.23410 (13)	−0.0800 (2)	0.07708 (16)	0.0553 (8)
C3	−0.30350 (13)	−0.0687 (2)	−0.00721 (17)	0.0605 (9)
C4	−0.33702 (12)	0.0320 (2)	−0.04231 (17)	0.0580 (9)
C5	−0.29776 (13)	0.1220 (2)	0.01114 (18)	0.0625 (9)
C6	−0.22799 (13)	0.11356 (19)	0.09640 (17)	0.0570 (9)
C7	−0.41344 (14)	0.0434 (3)	−0.13425 (18)	0.0807 (10)
C8	−0.03201 (13)	−0.09808 (19)	0.32890 (17)	0.0529 (8)
C9	0.01174 (15)	−0.19835 (19)	0.3795 (2)	0.0829 (10)
C10	−0.01225 (12)	0.01440 (18)	0.35383 (16)	0.0470 (7)
C11	−0.07411 (12)	0.07485 (18)	0.27784 (16)	0.0498 (8)
C12	0.04790 (12)	0.06930 (19)	0.42923 (16)	0.0529 (8)
C13	0.11229 (12)	0.01857 (19)	0.51147 (15)	0.0524 (8)
C14	0.16670 (12)	0.07441 (19)	0.58368 (16)	0.0558 (8)
C15	0.23504 (12)	0.03180 (18)	0.66822 (15)	0.0468 (8)
C16	0.28189 (12)	0.10222 (17)	0.74142 (16)	0.0484 (7)
C17	0.34695 (11)	0.06209 (17)	0.82033 (15)	0.0462 (7)
C18	0.36860 (12)	−0.04585 (19)	0.83085 (17)	0.0533 (8)
C19	0.32218 (13)	−0.11635 (19)	0.75823 (18)	0.0594 (9)
C20	0.25664 (13)	−0.07833 (19)	0.67876 (17)	0.0558 (8)
H2	−0.21290	−0.14941	0.09841	0.0664*
H2A	0.00843	0.19892	0.38131	0.0985*
H3	−0.32857	−0.13128	−0.04158	0.0726*
H5	−0.31886	0.19129	−0.01079	0.0749*
H6	−0.20295	0.17621	0.13074	0.0684*
H7A	−0.41585	−0.01104	−0.17713	0.1210*
H7B	−0.41647	0.11515	−0.15951	0.1210*
H7C	−0.45667	0.03326	−0.12467	0.1210*
H9A	0.01385	−0.20300	0.43799	0.1245*
H9B	0.06423	−0.19504	0.39072	0.1245*
H9C	−0.01457	−0.26184	0.34237	0.1245*
H13	0.11552	−0.05758	0.51357	0.0629*
H14	0.16074	0.15024	0.58025	0.0669*
H16	0.26930	0.17631	0.73710	0.0581*
H18	0.41302	−0.07088	0.88501	0.0640*
H19	0.33541	−0.19024	0.76316	0.0712*
H20	0.22594	−0.12729	0.63083	0.0669*

	U11	U22	U33	U12	U13	U23
O1	0.0611 (11)	0.0537 (9)	0.0678 (13)	0.0053 (8)	0.0077 (10)	0.0014 (9)
O2	0.0631 (12)	0.0662 (11)	0.0690 (15)	0.0031 (8)	0.0003 (10)	−0.0037 (10)
O3	0.0780 (12)	0.0638 (11)	0.0603 (13)	0.0089 (9)	0.0141 (10)	−0.0164 (10)
O4	0.0616 (12)	0.0917 (13)	0.0686 (14)	0.0114 (10)	−0.0097 (11)	−0.0236 (11)
N1	0.0395 (10)	0.0538 (10)	0.0368 (11)	0.0017 (8)	0.0119 (9)	0.0074 (9)
N2	0.0505 (11)	0.0524 (11)	0.0455 (13)	−0.0008 (9)	0.0091 (11)	0.0111 (10)
N3	0.0515 (12)	0.0620 (13)	0.0438 (14)	0.0006 (10)	0.0127 (11)	−0.0069 (11)
C1	0.0357 (11)	0.0600 (14)	0.0367 (14)	0.0024 (10)	0.0158 (11)	0.0056 (12)
C2	0.0492 (13)	0.0615 (14)	0.0434 (15)	0.0006 (11)	0.0156 (13)	0.0049 (13)
C3	0.0494 (14)	0.0755 (17)	0.0424 (16)	−0.0071 (12)	0.0138 (13)	−0.0026 (14)
C4	0.0393 (12)	0.0889 (18)	0.0383 (14)	0.0042 (13)	0.0147 (12)	0.0052 (15)
C5	0.0512 (14)	0.0725 (17)	0.0488 (17)	0.0145 (12)	0.0154 (14)	0.0123 (14)
C6	0.0497 (14)	0.0627 (15)	0.0462 (16)	0.0065 (11)	0.0161 (13)	0.0020 (12)
C7	0.0519 (14)	0.118 (2)	0.0482 (17)	0.0107 (15)	0.0090 (14)	0.0060 (17)
C8	0.0438 (13)	0.0600 (14)	0.0410 (15)	−0.0024 (10)	0.0121 (12)	0.0089 (12)
C9	0.0701 (17)	0.0590 (15)	0.071 (2)	−0.0015 (13)	0.0023 (16)	0.0208 (15)
C10	0.0364 (11)	0.0599 (14)	0.0382 (13)	−0.0017 (10)	0.0148 (11)	0.0039 (12)
C11	0.0426 (13)	0.0560 (14)	0.0432 (15)	0.0002 (11)	0.0169 (12)	0.0001 (12)
C12	0.0452 (13)	0.0583 (14)	0.0481 (16)	0.0013 (11)	0.0192 (13)	0.0009 (13)
C13	0.0395 (12)	0.0648 (14)	0.0394 (15)	−0.0024 (11)	0.0108 (12)	−0.0002 (13)
C14	0.0469 (13)	0.0640 (14)	0.0457 (16)	0.0008 (11)	0.0164 (13)	0.0018 (13)
C15	0.0394 (12)	0.0590 (14)	0.0367 (13)	−0.0045 (10)	0.0160 (11)	−0.0026 (12)
C16	0.0458 (12)	0.0510 (12)	0.0426 (14)	0.0001 (10)	0.0187 (12)	−0.0044 (12)
C17	0.0406 (12)	0.0556 (13)	0.0352 (13)	−0.0061 (10)	0.0146 (12)	−0.0081 (12)
C18	0.0424 (12)	0.0589 (14)	0.0462 (15)	0.0034 (11)	0.0141 (12)	0.0009 (13)
C19	0.0539 (14)	0.0516 (13)	0.0542 (17)	−0.0058 (11)	0.0150 (14)	−0.0048 (13)
C20	0.0475 (13)	0.0571 (14)	0.0496 (16)	−0.0116 (11)	0.0159 (13)	−0.0092 (13)

O1—C11	1.259 (3)	C14—C15	1.458 (3)
O2—C12	1.310 (3)	C15—C20	1.393 (3)
O3—N3	1.209 (3)	C15—C16	1.387 (3)
O4—N3	1.219 (3)	C16—C17	1.373 (3)
O2—H2A	0.8200	C17—C18	1.367 (3)
N1—C1	1.421 (3)	C18—C19	1.380 (3)
N1—C11	1.360 (3)	C19—C20	1.373 (4)
N1—N2	1.401 (2)	C2—H2	0.9300
N2—C8	1.300 (3)	C3—H3	0.9300
N3—C17	1.462 (3)	C5—H5	0.9300
C1—C2	1.377 (3)	C6—H6	0.9300
C1—C6	1.381 (3)	C7—H7A	0.9600
C2—C3	1.377 (4)	C7—H7B	0.9600
C3—C4	1.375 (3)	C7—H7C	0.9600
C4—C5	1.375 (4)	C9—H9A	0.9600
C4—C7	1.508 (4)	C9—H9B	0.9600
C5—C6	1.386 (4)	C9—H9C	0.9600
C8—C10	1.428 (3)	C13—H13	0.9300
C8—C9	1.485 (4)	C14—H14	0.9300
C10—C11	1.433 (3)	C16—H16	0.9300
C10—C12	1.381 (3)	C18—H18	0.9300
C12—C13	1.446 (3)	C19—H19	0.9300
C13—C14	1.319 (3)	C20—H20	0.9300
C12—O2—H2A	109.00	C16—C17—C18	122.9 (2)
N2—N1—C11	110.88 (18)	N3—C17—C16	118.21 (19)
C1—N1—C11	130.70 (18)	C17—C18—C19	117.6 (2)
N2—N1—C1	118.39 (17)	C18—C19—C20	120.6 (2)
N1—N2—C8	107.02 (18)	C15—C20—C19	121.6 (2)
O3—N3—C17	119.0 (2)	C1—C2—H2	120.00
O4—N3—C17	118.1 (2)	C3—C2—H2	120.00
O3—N3—O4	122.9 (2)	C2—C3—H3	119.00
N1—C1—C6	121.2 (2)	C4—C3—H3	119.00
C2—C1—C6	119.0 (2)	C4—C5—H5	119.00
N1—C1—C2	119.8 (2)	C6—C5—H5	119.00
C1—C2—C3	120.2 (2)	C1—C6—H6	120.00
C2—C3—C4	122.3 (2)	C5—C6—H6	120.00
C3—C4—C7	121.8 (2)	C4—C7—H7A	109.00
C5—C4—C7	121.5 (2)	C4—C7—H7B	109.00
C3—C4—C5	116.7 (2)	C4—C7—H7C	109.00
C4—C5—C6	122.6 (2)	H7A—C7—H7B	109.00
C1—C6—C5	119.3 (2)	H7A—C7—H7C	109.00
N2—C8—C9	119.4 (2)	H7B—C7—H7C	109.00
N2—C8—C10	111.4 (2)	C8—C9—H9A	109.00
C9—C8—C10	129.3 (2)	C8—C9—H9B	109.00
C8—C10—C12	135.2 (2)	C8—C9—H9C	109.00
C11—C10—C12	120.0 (2)	H9A—C9—H9B	110.00
C8—C10—C11	104.8 (2)	H9A—C9—H9C	110.00
O1—C11—C10	127.3 (2)	H9B—C9—H9C	109.00
N1—C11—C10	105.93 (19)	C12—C13—H13	118.00
O1—C11—N1	126.7 (2)	C14—C13—H13	118.00
O2—C12—C13	115.6 (2)	C13—C14—H14	116.00
C10—C12—C13	125.7 (2)	C15—C14—H14	116.00
O2—C12—C10	118.8 (2)	C15—C16—H16	120.00
C12—C13—C14	123.6 (2)	C17—C16—H16	120.00
C13—C14—C15	127.9 (2)	C17—C18—H18	121.00
C14—C15—C20	122.5 (2)	C19—C18—H18	121.00
C16—C15—C20	117.6 (2)	C18—C19—H19	120.00
C14—C15—C16	119.9 (2)	C20—C19—H19	120.00
C15—C16—C17	119.7 (2)	C15—C20—H20	119.00
N3—C17—C18	118.9 (2)	C19—C20—H20	119.00
C1—N1—N2—C8	178.4 (2)	N2—C8—C10—C12	177.5 (3)
C11—N1—N2—C8	0.1 (3)	C9—C8—C10—C11	178.0 (3)
N2—N1—C1—C2	−3.6 (4)	C9—C8—C10—C12	−2.8 (5)
N2—N1—C1—C6	176.3 (2)	C8—C10—C11—O1	−178.1 (3)
C11—N1—C1—C2	174.2 (3)	C8—C10—C11—N1	1.7 (3)
C11—N1—C1—C6	−5.8 (4)	C12—C10—C11—O1	2.6 (4)
N2—N1—C11—O1	178.6 (3)	C12—C10—C11—N1	−177.7 (2)
N2—N1—C11—C10	−1.2 (3)	C8—C10—C12—O2	179.6 (3)
C1—N1—C11—O1	0.6 (5)	C8—C10—C12—C13	−1.2 (5)
C1—N1—C11—C10	−179.1 (3)	C11—C10—C12—O2	−1.3 (4)
N1—N2—C8—C9	−178.7 (2)	C11—C10—C12—C13	177.9 (3)
N1—N2—C8—C10	1.0 (3)	O2—C12—C13—C14	2.3 (4)
O3—N3—C17—C16	14.1 (4)	C10—C12—C13—C14	−177.0 (3)
O3—N3—C17—C18	−165.3 (2)	C12—C13—C14—C15	−177.9 (3)
O4—N3—C17—C16	−166.5 (2)	C13—C14—C15—C16	−173.4 (3)
O4—N3—C17—C18	14.1 (4)	C13—C14—C15—C20	7.5 (5)
N1—C1—C2—C3	179.2 (2)	C14—C15—C16—C17	−178.9 (2)
C6—C1—C2—C3	−0.8 (4)	C20—C15—C16—C17	0.2 (4)
N1—C1—C6—C5	−179.4 (3)	C14—C15—C20—C19	178.6 (3)
C2—C1—C6—C5	0.6 (4)	C16—C15—C20—C19	−0.5 (4)
C1—C2—C3—C4	0.6 (4)	C15—C16—C17—N3	−179.2 (2)
C2—C3—C4—C5	−0.1 (4)	C15—C16—C17—C18	0.1 (4)
C2—C3—C4—C7	−179.4 (3)	N3—C17—C18—C19	179.2 (2)
C3—C4—C5—C6	−0.2 (4)	C16—C17—C18—C19	−0.1 (4)
C7—C4—C5—C6	179.2 (3)	C17—C18—C19—C20	−0.2 (4)
C4—C5—C6—C1	−0.1 (4)	C18—C19—C20—C15	0.5 (4)
N2—C8—C10—C11	−1.7 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2A···O1	0.82	1.82	2.571 (3)	152
C6—H6···O1	0.93	2.33	2.958 (3)	125
C18—H18···O4i	0.93	2.57	3.496 (3)	171
C20—H20···O3ii	0.93	2.43	3.172 (3)	136

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2A⋯O1	0.82	1.82	2.571 (3)	152
C6—H6⋯O1	0.93	2.33	2.958 (3)	125
C18—H18⋯O4i	0.93	2.57	3.496 (3)	171
C20—H20⋯O3ii	0.93	2.43	3.172 (3)	136

Symmetry codes: (i) ; (ii) .