3-(2-Hydroxy­phen­yl)-5-(2-methoxy­phenyl)-1H-pyrazole

Hasan, A.; Ikram, S.; Badshah, A.; Bolte, M.; Zia, M.

doi:10.1107/S1600536808025725

organic compounds

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ISSN: 2056-9890

Volume 64| Part 9| September 2008| Page o1767

doi:10.1107/S1600536808025725

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3-(2-Hydroxyphenyl)-5-(2-methoxyphenyl)-1H-pyrazole

Aurangzeb Hasan,^a ^* Sumera Ikram,^a Amir Badshah,^a Michael Bolte ^b and Mehwash Zia ^a

^aDepartment of Chemistry, Quaid-i-Azam University, Islamabad 45320, Pakistan, and ^bInstitut für Anorganische Chemie, J. W. Goethe-Universität, Max-von-Laue-Strasse 7, 60438 Frankfurt/Main, Germany
^*Correspondence e-mail: flavonoids@hotmail.com

(Received 18 July 2008; accepted 9 August 2008; online 16 August 2008)

The title compound, C₁₆H₁₄N₂O₂, was derived from 1-(2-hydroxyphenyl)-3-(2-methoxyphenyl)propane-1,3-dione. The molecule is essentially planar (r.m.s. deviation for all non-H atoms = 0.089 Å). Two intramolecular hydrogen bonds stabilize the molecular 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_r = 266.29
Orthorhombic, P n a 2₁
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[F² > 2σ(F²)] = 0.034
wR(F²) = 0.090
S = 1.03
1777 reflections
191 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.16 e Å⁻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) $[-x+1, -y+2, z+{\script{1\over 2}}]$ .

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.

Supporting information

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

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

checkCIF report

Comment top

3,5-substituted Pyrazoles are important class of compounds.These have been proven to be a selective inhibitor of COX in isoenzyme in human blood and are used for the development of anti-inflamatory drugs and analgesic medicines (Ezava et al., 2005). Disubstituted pyrazoles have been reported as an important intermediate in the synthesis of herbicides (US patent 5191087, 1993; US patent 5698708, 1997) and for the treatmet of pain and disorders such as Arthritis (US patent 5908857, 1999).Pyrazoles are inhibitors of alchol dehydrogenase and have been found to be effective inhibitors for the oxidation of ethanol by liver microsomes (Feierman & Cederbaum, 1986). 3,5-disubstituted pyrazoles are also uesd to form solid dinuclear complexes (Sanz et al., 1998). The molecule is essentially planar (r.m.s. deviation for all non-H atoms 0.089 Å). Two intramolecular hydrogen bonds stabilize the molecular conformation and one N—H···O hydrogen bond is stabilizing the crystal structure.

Related literature top

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

Experimental top

1-(2'-hydroxyphenyl)-3-(2''-methoxyphenyl) propane-1,3-dione was prepared by a modified Baker Venkataram rearrangement as reported earlier (Ahmad et al., 1997). Purification was carried out by recrystallization using absolute ethanol. 1-H-3(2-hydroxyphenyl)-5-(2-methoxyphenyl) pyrazole was synthesized by reacting hydrazine hydrate (0.5 g, 10 mmol) with 1-(2-hydroxyphenyl)-3-(2-methoxyphenyl) propane-1,3-dione (2.7 g, 10 mmol) in 100 ml of absolute ethanol. The mixture was refluxed for seven hours. Solvent was removed under reduced pressure. Compound (II) was synthesized by adding 0.1 mole of phenyl hydrazine in 0.1 mole of compound (II) dissolved in 200 ml of absolute ethanol. The mixture was refluxed for 7 h. Solvent was removed under reduced pressure. Highly viscous residue was recrystallized using absolute ethanol. (Yield: 96%, m.p: 456k)

Computing details top

Data collection: X-AREA (Stoe & Cie, 2001); cell refinement: X-AREA (Stoe & Cie, 2001); data reduction: X-AREA (Stoe & Cie, 2001); 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 (Sheldrick, 2008).

Figures top

Fig. 1. Perspective view of the title compound with the atom numbering scheme; displacement ellipsoids are at the 50% probability level; H atoms are drawn as small spheres of arbitrary radii.

3-(2-Hydroxyphenyl)-5-(2-methoxyphenyl)-1H-pyrazole top

Crystal data top

C₁₆H₁₄N₂O₂	D_x = 1.322 Mg m⁻³
M_r = 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 = 3.4–29.6°
b = 10.2239 (7) Å	µ = 0.09 mm⁻¹
c = 7.4513 (7) Å	T = 173 K
V = 1337.94 (19) Å³	Block, light yellow
Z = 4	0.27 × 0.25 × 0.24 mm
F(000) = 560

Data collection top

Stoe IPDSII two-circle diffractometer	1620 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.057
Graphite monochromator	θ_max = 28.3°, θ_min = 3.6°
ω scans	h = −20→23
10969 measured reflections	k = −11→13
1777 independent reflections	l = −8→9

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)] = 0.034	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.091	w = 1/[σ²(F_o²) + (0.0644P)² + 0.0395P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max < 0.001
1777 reflections	Δρ_max = 0.18 e Å⁻³
191 parameters	Δρ_min = −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)

Crystal data top

C₁₆H₁₄N₂O₂	V = 1337.94 (19) Å³
M_r = 266.29	Z = 4
Orthorhombic, Pna2₁	Mo Kα radiation
a = 17.5626 (15) Å	µ = 0.09 mm⁻¹
b = 10.2239 (7) Å	T = 173 K
c = 7.4513 (7) Å	0.27 × 0.25 × 0.24 mm

Data collection top

Stoe IPDSII two-circle diffractometer	1620 reflections with I > 2σ(I)
10969 measured reflections	R_int = 0.057
1777 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.034	1 restraint
wR(F²) = 0.091	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.18 e Å⁻³
1777 reflections	Δρ_min = −0.16 e Å⁻³
191 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	0.49830 (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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x+1, −y+2, z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₆H₁₄N₂O₂
M_r	266.29
Crystal system, space group	Orthorhombic, Pna2₁
Temperature (K)	173
a, b, c (Å)	17.5626 (15), 10.2239 (7), 7.4513 (7)
V (Å³)	1337.94 (19)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.27 × 0.25 × 0.24

Data collection
Diffractometer	Stoe IPDSII two-circle diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	10969, 1777, 1620
R_int	0.057
(sin θ/λ)_max (Å⁻¹)	0.667

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.034, 0.091, 1.03
No. of reflections	1777
No. of parameters	191
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.18, −0.16

Computer programs: X-AREA (Stoe & Cie, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), XP in SHELXTL-Plus (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

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) −x+1, −y+2, z+1/2.

Acknowledgements

AH is grateful to the Higher Education Commission of Pakistan for a grant.

References

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