(4Z)-4-[(2E)-1-Hydr-oxy-3-(4-methoxy-phen-yl)prop-2-en-ylidene]-3-methyl-1-phenyl-1H-pyrazol-5(4H)-one.

The title compound, C(20)H(18)N(2)O(4), is a chalcone derivative of pyrazole. The pyrazole ring is inclined at a dihedral angle of 19.29 (12)° to the methoxy-phenyl ring mean plane, and by 1.19 (13)° to the phenyl ring. The mol-ecular structure is stabilized by an intra-molecular 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 = 334.36

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.094

S = 1.05

2056 reflections

229 parameters

2 restraints

H-atom parameters constrained

Δρmax = 0.10 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: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON.

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

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

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

C20H18N2O3	F(000) = 704
Mr = 334.36	Dx = 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

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

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(Fo2) + (0.0492P)2 + 0.0958P] where P = (Fo2 + 2Fc2)/3
2056 reflections	(Δ/σ)max < 0.001
229 parameters	Δρmax = 0.10 e Å−3
2 restraints	Δρmin = −0.16 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 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.

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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

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