3-(2-Hydroxy-phen-yl)-5-(2-methoxy-phenyl)-1H-pyrazole.

The title compound, C(16)H(14)N(2)O(2), was derived from 1-(2-hydroxy-phen-yl)-3-(2-methoxy-phen-yl)propane-1,3-dione. The mol-ecule is essentially planar (r.m.s. deviation for all non-H atoms = 0.089 Å). Two intra-molecular hydrogen bonds stabilize the mol-ecular conformation and one N-H⋯O hydrogen bond stabilizes the crystal structure.

Related literature

For related literature, see: Ahmad et al. (1990 ▶, 1997 ▶); Ezava et al. (2005 ▶); Feierman & Cederbaum (1986 ▶); Sanz et al. (1998 ▶); Alcaraz et al. (1993 ▶); Hamper et al. (1997 ▶); Fujio (1999 ▶).

Experimental

Crystal data

C16H14N2O2

M = 266.29

Orthorhombic,

a = 17.5626 (15) Å

b = 10.2239 (7) Å

c = 7.4513 (7) Å

V = 1337.94 (19) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 173 (2) K

0.27 × 0.25 × 0.24 mm

Data collection

Stoe IPDSII two-circle diffractometer

Absorption correction: none

10969 measured reflections

1777 independent reflections

1620 reflections with I > 2σ(I)

R int = 0.057

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.090

S = 1.03

1777 reflections

191 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.18 e Å−3

Δρmin = −0.16 e Å−3

Data collection: X-AREA (Stoe & Cie, 2001 ▶); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: XP in SHELXTL-Plus (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808025725/bx2163sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808025725/bx2163Isup2.hkl

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

C16H14N2O2	Dx = 1.322 Mg m−3
Mr = 266.29	Melting point: 456 K
Orthorhombic, Pna21	Mo Kα radiation λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 11915 reflections
a = 17.5626 (15) Å	θ = 3.4–29.6º
b = 10.2239 (7) Å	µ = 0.09 mm−1
c = 7.4513 (7) Å	T = 173 (2) K
V = 1337.94 (19) Å3	Block, light yellow
Z = 4	0.27 × 0.25 × 0.24 mm
F000 = 560

Stoe IPDSII two-circle diffractometer	1620 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.057
Monochromator: graphite	θmax = 28.3º
T = 173(2) K	θmin = 3.6º
ω scans	h = −20→23
Absorption correction: none	k = −11→13
10969 measured reflections	l = −8→9
1777 independent 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)] = 0.034	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.091	w = 1/[σ2(Fo2) + (0.0644P)2 + 0.0395P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max < 0.001
1777 reflections	Δρmax = 0.18 e Å−3
191 parameters	Δρmin = −0.16 e Å−3
1 restraint	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.049 (6)

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	0.49830 (7)	0.72482 (13)	0.76358 (19)	0.0401 (3)
O2	0.42612 (9)	1.04511 (15)	0.0584 (2)	0.0507 (4)
H2	0.441 (2)	0.992 (4)	0.165 (6)	0.093 (11)*
N1	0.44362 (8)	0.80017 (15)	0.4520 (2)	0.0340 (3)
H1	0.4833 (15)	0.825 (3)	0.525 (4)	0.058 (7)*
N2	0.43083 (8)	0.86611 (15)	0.2984 (2)	0.0369 (3)
C1	0.39489 (9)	0.69783 (15)	0.4736 (2)	0.0289 (3)
C2	0.34823 (9)	0.69776 (15)	0.3232 (2)	0.0306 (3)
H2A	0.3083	0.6381	0.2968	0.037*
C3	0.37225 (9)	0.80434 (16)	0.2179 (2)	0.0304 (3)
C11	0.39509 (9)	0.61110 (16)	0.6314 (2)	0.0306 (3)
C12	0.44651 (9)	0.62379 (17)	0.7757 (2)	0.0339 (3)
C13	0.44373 (11)	0.5373 (2)	0.9203 (3)	0.0425 (4)
H13	0.4788	0.5461	1.0165	0.051*
C14	0.38945 (12)	0.4381 (2)	0.9235 (3)	0.0461 (5)
H14	0.3882	0.3786	1.0214	0.055*
C15	0.33733 (11)	0.42539 (19)	0.7852 (3)	0.0437 (4)
H15	0.2998	0.3585	0.7891	0.052*
C16	0.34031 (10)	0.51098 (17)	0.6410 (3)	0.0353 (4)
H16	0.3045	0.5018	0.5463	0.042*
C17	0.55036 (12)	0.7438 (3)	0.9090 (3)	0.0520 (5)
H17A	0.5825	0.6660	0.9222	0.078*
H17B	0.5218	0.7583	1.0202	0.078*
H17C	0.5825	0.8201	0.8843	0.078*
C31	0.34524 (9)	0.85273 (17)	0.0429 (2)	0.0314 (3)
C32	0.37398 (10)	0.96997 (18)	−0.0313 (3)	0.0367 (4)
C33	0.34958 (11)	1.0130 (2)	−0.1993 (3)	0.0438 (4)
H33	0.3693	1.0919	−0.2482	0.053*
C34	0.29652 (12)	0.9407 (2)	−0.2952 (3)	0.0437 (4)
H34	0.2805	0.9700	−0.4102	0.052*
C35	0.26648 (11)	0.82574 (19)	−0.2245 (3)	0.0417 (4)
H35	0.2297	0.7772	−0.2900	0.050*
C36	0.29090 (10)	0.78266 (17)	−0.0569 (2)	0.0354 (4)
H36	0.2704	0.7041	−0.0089	0.042*

	U11	U22	U33	U12	U13	U23
O1	0.0371 (6)	0.0507 (8)	0.0327 (6)	−0.0037 (5)	−0.0084 (5)	0.0025 (6)
O2	0.0531 (8)	0.0541 (8)	0.0448 (8)	−0.0219 (7)	−0.0050 (7)	0.0142 (7)
N1	0.0363 (7)	0.0385 (7)	0.0273 (7)	−0.0070 (6)	−0.0052 (6)	0.0026 (6)
N2	0.0390 (7)	0.0402 (7)	0.0314 (8)	−0.0087 (6)	−0.0060 (6)	0.0038 (6)
C1	0.0298 (7)	0.0302 (7)	0.0268 (8)	0.0005 (6)	−0.0005 (6)	−0.0037 (6)
C2	0.0306 (7)	0.0329 (7)	0.0283 (8)	−0.0029 (6)	−0.0024 (6)	−0.0014 (6)
C3	0.0304 (7)	0.0336 (8)	0.0271 (8)	−0.0008 (6)	−0.0013 (6)	−0.0018 (6)
C11	0.0325 (7)	0.0330 (7)	0.0263 (7)	0.0057 (6)	0.0020 (6)	−0.0017 (6)
C12	0.0325 (7)	0.0394 (8)	0.0299 (8)	0.0063 (6)	0.0008 (6)	−0.0018 (7)
C13	0.0413 (9)	0.0537 (11)	0.0326 (9)	0.0113 (8)	−0.0018 (7)	0.0071 (8)
C14	0.0493 (10)	0.0513 (11)	0.0378 (10)	0.0074 (8)	0.0033 (8)	0.0156 (9)
C15	0.0476 (9)	0.0410 (9)	0.0426 (11)	−0.0005 (7)	0.0046 (8)	0.0065 (8)
C16	0.0389 (8)	0.0333 (8)	0.0337 (9)	0.0004 (7)	0.0005 (7)	−0.0010 (7)
C17	0.0431 (10)	0.0746 (14)	0.0384 (11)	−0.0055 (10)	−0.0137 (8)	0.0031 (10)
C31	0.0314 (7)	0.0365 (8)	0.0263 (8)	0.0041 (6)	0.0016 (6)	−0.0006 (6)
C32	0.0357 (8)	0.0434 (9)	0.0310 (9)	−0.0011 (7)	0.0048 (7)	0.0015 (7)
C33	0.0483 (10)	0.0488 (10)	0.0342 (10)	0.0069 (8)	0.0084 (8)	0.0103 (8)
C34	0.0510 (10)	0.0530 (10)	0.0271 (8)	0.0189 (9)	−0.0001 (7)	0.0001 (8)
C35	0.0464 (9)	0.0464 (9)	0.0324 (9)	0.0122 (7)	−0.0083 (7)	−0.0067 (8)
C36	0.0384 (8)	0.0370 (8)	0.0307 (8)	0.0036 (7)	−0.0040 (7)	−0.0037 (7)

O1—C12	1.379 (2)	C14—C15	1.384 (3)
O1—C17	1.431 (2)	C14—H14	0.9500
O2—C32	1.369 (2)	C15—C16	1.387 (3)
O2—H2	0.99 (4)	C15—H15	0.9500
N1—N2	1.347 (2)	C16—H16	0.9500
N1—C1	1.361 (2)	C17—H17A	0.9800
N1—H1	0.92 (3)	C17—H17B	0.9800
N2—C3	1.348 (2)	C17—H17C	0.9800
C1—C2	1.388 (2)	C31—C36	1.406 (2)
C1—C11	1.473 (2)	C31—C32	1.413 (2)
C2—C3	1.408 (2)	C32—C33	1.395 (3)
C2—H2A	0.9500	C33—C34	1.387 (3)
C3—C31	1.473 (2)	C33—H33	0.9500
C11—C16	1.407 (2)	C34—C35	1.392 (3)
C11—C12	1.410 (2)	C34—H34	0.9500
C12—C13	1.394 (3)	C35—C36	1.392 (3)
C13—C14	1.392 (3)	C35—H35	0.9500
C13—H13	0.9500	C36—H36	0.9500
C12—O1—C17	118.24 (16)	C16—C15—H15	120.2
C32—O2—H2	105 (2)	C15—C16—C11	121.61 (18)
N2—N1—C1	112.35 (14)	C15—C16—H16	119.2
N2—N1—H1	119.2 (18)	C11—C16—H16	119.2
C1—N1—H1	128.3 (18)	O1—C17—H17A	109.5
N1—N2—C3	105.72 (14)	O1—C17—H17B	109.5
N1—C1—C2	106.03 (15)	H17A—C17—H17B	109.5
N1—C1—C11	123.76 (15)	O1—C17—H17C	109.5
C2—C1—C11	130.20 (14)	H17A—C17—H17C	109.5
C1—C2—C3	105.82 (14)	H17B—C17—H17C	109.5
C1—C2—H2A	127.1	C36—C31—C32	117.91 (16)
C3—C2—H2A	127.1	C36—C31—C3	121.03 (15)
N2—C3—C2	110.08 (15)	C32—C31—C3	121.05 (16)
N2—C3—C31	118.85 (15)	O2—C32—C33	117.80 (17)
C2—C3—C31	131.07 (15)	O2—C32—C31	121.61 (17)
C16—C11—C12	117.79 (16)	C33—C32—C31	120.59 (18)
C16—C11—C1	118.49 (15)	C34—C33—C32	120.02 (18)
C12—C11—C1	123.71 (15)	C34—C33—H33	120.0
O1—C12—C13	123.28 (17)	C32—C33—H33	120.0
O1—C12—C11	116.16 (15)	C33—C34—C35	120.64 (18)
C13—C12—C11	120.56 (17)	C33—C34—H34	119.7
C14—C13—C12	119.95 (18)	C35—C34—H34	119.7
C14—C13—H13	120.0	C36—C35—C34	119.34 (18)
C12—C13—H13	120.0	C36—C35—H35	120.3
C15—C14—C13	120.55 (18)	C34—C35—H35	120.3
C15—C14—H14	119.7	C35—C36—C31	121.49 (17)
C13—C14—H14	119.7	C35—C36—H36	119.3
C14—C15—C16	119.51 (18)	C31—C36—H36	119.3
C14—C15—H15	120.2
C1—N1—N2—C3	−0.2 (2)	C12—C13—C14—C15	−0.9 (3)
N2—N1—C1—C2	0.46 (19)	C13—C14—C15—C16	1.2 (3)
N2—N1—C1—C11	−178.61 (14)	C14—C15—C16—C11	−0.1 (3)
N1—C1—C2—C3	−0.50 (18)	C12—C11—C16—C15	−1.2 (3)
C11—C1—C2—C3	178.48 (16)	C1—C11—C16—C15	179.75 (16)
N1—N2—C3—C2	−0.1 (2)	N2—C3—C31—C36	172.07 (16)
N1—N2—C3—C31	−179.01 (14)	C2—C3—C31—C36	−6.5 (3)
C1—C2—C3—N2	0.4 (2)	N2—C3—C31—C32	−7.0 (2)
C1—C2—C3—C31	179.10 (16)	C2—C3—C31—C32	174.43 (18)
N1—C1—C11—C16	178.05 (15)	C36—C31—C32—O2	178.95 (17)
C2—C1—C11—C16	−0.8 (3)	C3—C31—C32—O2	−2.0 (3)
N1—C1—C11—C12	−0.9 (2)	C36—C31—C32—C33	−0.8 (2)
C2—C1—C11—C12	−179.75 (17)	C3—C31—C32—C33	178.21 (15)
C17—O1—C12—C13	−1.8 (3)	O2—C32—C33—C34	−179.68 (18)
C17—O1—C12—C11	178.37 (16)	C31—C32—C33—C34	0.1 (3)
C16—C11—C12—O1	−178.60 (15)	C32—C33—C34—C35	0.7 (3)
C1—C11—C12—O1	0.4 (2)	C33—C34—C35—C36	−0.8 (3)
C16—C11—C12—C13	1.5 (2)	C34—C35—C36—C31	0.1 (3)
C1—C11—C12—C13	−179.50 (16)	C32—C31—C36—C35	0.8 (2)
O1—C12—C13—C14	179.62 (17)	C3—C31—C36—C35	−178.30 (16)
C11—C12—C13—C14	−0.5 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···N2	0.99 (4)	1.64 (4)	2.560 (2)	152 (3)
N1—H1···O1	0.92 (3)	2.07 (3)	2.628 (2)	118 (2)
N1—H1···O2i	0.92 (3)	2.09 (3)	2.892 (2)	146 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯N2	0.99 (4)	1.64 (4)	2.560 (2)	152 (3)
N1—H1⋯O1	0.92 (3)	2.07 (3)	2.628 (2)	118 (2)
N1—H1⋯O2i	0.92 (3)	2.09 (3)	2.892 (2)	146 (3)

Symmetry code: (i) .