(Furan-2-yl)(5-hy­droxy-3-methyl-5-phenyl-4,5-dihydro-1H-pyrazol-1-yl)methanone

Kargar, H.; Kia, R.; Moghadamm, M.; Tahir, M.N.

doi:10.1107/S1600536811000948

organic compounds

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ISSN: 2056-9890

Volume 67| Part 2| February 2011| Page o367

doi:10.1107/S1600536811000948

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(Furan-2-yl)(5-hydroxy-3-methyl-5-phenyl-4,5-dihydro-1H-pyrazol-1-yl)methanone

Hadi Kargar,^a Reza Kia,^b,^c ^* Majid Moghadamm ^d and Muhammad Nawaz Tahir ^e ^*

^aDepartment of Chemistry, School of Science, Payame Noor University (PNU), Ardakan, Yazd, Iran, ^bX-ray Crystallography Lab., Plasma Physics Research Center, Science and Research Branch, Islamic Azad University, Tehran, Iran, ^cDepartment of Chemistry, Science and Research Branch, Islamic Azad University, Tehran, Iran, ^dDepartment of Chemistry, Catalysis Division, University of Isfahan, Isfahan 81746-73441, Iran, and ^eDepartment of Physics, University of Sargodha, Punjab, Pakistan
^*Correspondence e-mail: rkia@srbiau.ac.ir, zsrkk@yahoo.com, dmntahir_uos@yahoo.com

(Received 2 January 2011; accepted 7 January 2011; online 12 January 2011)

In the title compound, C₁₅H₁₄N₂O₃, the furan ring is disordered over two positions with a refined site-occupancy ratio of 0.587 (11):0.413 (11). The mean plane of the approximately planar pyrazole ring [maximum deviation = 0.0469 (11) Å] makes dihedral angles of 86.13 (11) and 4.5 (5)° with the phenyl and furan rings, respectively. The dihedral angle between the phenyl ring and the major component of the disordered furan ring is 81.8 (5)°. The molecule shows chirality in one of the carbon atoms but the centrosymmetric space group means the compound is a racemic mixture. In the crystal, intermolecular O—H⋯O and C—H⋯O hydrogen bonds connect the molecules. The crystal structure is further stabilized by π–π stacking interactions with a centroid–centroid distance of 3.8646 (12) Å.

Related literature

For standard bond lengths, see: Allen et al. (1987 ).

Experimental

Crystal data

C₁₅H₁₄N₂O₃
M_r = 270.28
Monoclinic, P 2₁ /n
a = 10.6844 (10) Å
b = 8.4700 (7) Å
c = 15.3022 (16) Å
β = 95.266 (3)°
V = 1379.0 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 296 K
0.28 × 0.22 × 0.16 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.975, T_max = 0.985
10534 measured reflections
2495 independent reflections
1615 reflections with I > 2σ(I)
R_int = 0.044

Refinement

R[F² > 2σ(F²)] = 0.042
wR(F²) = 0.106
S = 1.03
2495 reflections
221 parameters
10 restraints
H-atom parameters constrained
Δρ_max = 0.12 e Å⁻³
Δρ_min = −0.13 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O2ⁱ	0.82	2.02	2.7786 (18)	153
C14—H14A⋯O1ⁱⁱ	0.93	2.36	3.271 (9)	168
Symmetry codes: (i) -x+1, -y+2, -z; (ii) $[x-{\script{1\over 2}}, -y+{\script{5\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811000948/jh2253sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811000948/jh2253Isup2.hkl

checkCIF report

Comment top

The asymmetric unit of the title compound, Fig. 1, comprises a substituted pyrazole. The furane ring shows flip-flop rotational disorder in two positions with refined site occupancy ratio of 0.587 (11)/0.413 (11). The mean plane of the approximately planar pyrazole ring [maximum deviation = 0.0469 (11)Å] makes dihedral angles of 86.13 (11) and 4.5 (5)° with phenyl and the major component of the furane rings, respectively. The dihedral angle between the phenyl ring and the major component of the disordered furane ring is 81.8 (5)°.

In the crystal structure, intermolecular O—H···O and C—H···O hydrogen bonds connect the components of the structure. The crystal structure is further stabilized by π–π stacking interactions [Cg1···Cg2ⁱⁱⁱ = 3.8646 (12)Å, (iii) x, y, z; Cg1 and Cg2 are the centroid of pyrazole and phenyl rings, respectively].

Related literature top

For standard bond lengths, see: Allen et al. (1987).

Experimental top

The title compound was synthesized by adding furan-2-carbohydrazide (2 mmol) to a solution of benzoylacetone (2 mmol) in ethanol (20 ml). The mixture was refluxed with stirring for half an hour. The resultant solution was filtered and the white single crystals suitable for X-ray structure determination were recrystallized from ethanol by slow evaporation of the solvents at room temperature over several days.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular of the title compound, showing 40% probability displacement ellipsoids and the atomic numbering. The open bonds show the minor component of disordered furane ring.
	Fig. 2. The packing of the compound viewed along the b-axis showing connecting of molecules through hydrogen bonds. All H atoms removed except those involved in the hydrogen bonds. Hydrogen bonds are shown as dashed lines.

(Furan-2-yl)(5-hydroxy-3-methyl-5-phenyl-4,5-dihydro-1H- pyrazol-1-yl)methanone top

Crystal data top

C₁₅H₁₄N₂O₃	F(000) = 568
M_r = 270.28	D_x = 1.302 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2245 reflections
a = 10.6844 (10) Å	θ = 2.5–29.5°
b = 8.4700 (7) Å	µ = 0.09 mm⁻¹
c = 15.3022 (16) Å	T = 296 K
β = 95.266 (3)°	Block, white
V = 1379.0 (2) Å³	0.28 × 0.22 × 0.16 mm
Z = 4

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	2495 independent reflections
Radiation source: fine-focus sealed tube	1615 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.044
ϕ and ω scans	θ_max = 25.2°, θ_min = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −12→12
T_min = 0.975, T_max = 0.985	k = −10→10
10534 measured reflections	l = −18→18

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)] = 0.042	H-atom parameters constrained
wR(F²) = 0.106	w = 1/[σ²(F_o²) + (0.037P)² + 0.1913P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max < 0.001
2495 reflections	Δρ_max = 0.12 e Å⁻³
221 parameters	Δρ_min = −0.13 e Å⁻³
10 restraints	Extinction correction: SHELXTL (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0132 (14)

Crystal data top

C₁₅H₁₄N₂O₃	V = 1379.0 (2) Å³
M_r = 270.28	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 10.6844 (10) Å	µ = 0.09 mm⁻¹
b = 8.4700 (7) Å	T = 296 K
c = 15.3022 (16) Å	0.28 × 0.22 × 0.16 mm
β = 95.266 (3)°

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	2495 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	1615 reflections with I > 2σ(I)
T_min = 0.975, T_max = 0.985	R_int = 0.044
10534 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	10 restraints
wR(F²) = 0.106	H-atom parameters constrained
S = 1.03	Δρ_max = 0.12 e Å⁻³
2495 reflections	Δρ_min = −0.13 e Å⁻³
221 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	Occ. (<1)
O1	0.39871 (12)	1.05521 (16)	0.13086 (9)	0.0564 (4)
H1	0.4501	1.0373	0.0954	0.085*
O2	0.37249 (12)	0.97468 (15)	−0.05954 (9)	0.0540 (4)
N1	0.11933 (14)	1.14352 (17)	0.03952 (12)	0.0530 (5)
N2	0.22305 (14)	1.04995 (17)	0.02389 (10)	0.0463 (4)
C1	0.30125 (18)	0.8002 (2)	0.09202 (12)	0.0467 (5)
C2	0.4147 (2)	0.7260 (2)	0.10936 (14)	0.0605 (6)
H2	0.4856	0.7842	0.1289	0.073*
C3	0.4242 (3)	0.5637 (3)	0.09779 (18)	0.0803 (8)
H3	0.5016	0.5142	0.1091	0.096*
C4	0.3208 (3)	0.4768 (3)	0.0700 (2)	0.0916 (9)
H4	0.3272	0.3682	0.0630	0.110*
C5	0.2085 (3)	0.5500 (3)	0.0528 (2)	0.0909 (9)
H5	0.1378	0.4910	0.0337	0.109*
C6	0.1979 (2)	0.7105 (2)	0.06307 (16)	0.0704 (7)
H6	0.1203	0.7591	0.0504	0.085*
C7	0.28639 (17)	0.9765 (2)	0.10487 (13)	0.0455 (5)
C8	0.19276 (18)	1.0218 (2)	0.17109 (14)	0.0569 (6)
H8A	0.1500	0.9292	0.1909	0.068*
H8B	0.2350	1.0751	0.2216	0.068*
C9	0.10301 (18)	1.1294 (2)	0.12079 (15)	0.0545 (5)
C10	0.0004 (2)	1.2167 (3)	0.15998 (16)	0.0818 (8)
H10A	−0.0483	1.1441	0.1912	0.123*
H10B	−0.0530	1.2667	0.1142	0.123*
H10C	0.0363	1.2955	0.1998	0.123*
C11	0.27454 (17)	1.0491 (2)	−0.05355 (13)	0.0436 (5)
C12	0.21378 (16)	1.1311 (2)	−0.12971 (12)	0.0497 (5)
C13	0.1182 (12)	1.2333 (18)	−0.1440 (6)	0.071 (3)	0.587 (11)
H13A	0.0724	1.2811	−0.1024	0.085*	0.587 (11)
C14	0.1026 (12)	1.2525 (13)	−0.2367 (6)	0.071 (3)	0.587 (11)
H14A	0.0360	1.3042	−0.2680	0.086*	0.587 (11)
C15	0.1996 (12)	1.1838 (19)	−0.2715 (7)	0.076 (3)	0.587 (11)
H15A	0.2191	1.1926	−0.3293	0.092*	0.587 (11)
O3	0.2646 (7)	1.0983 (13)	−0.2065 (3)	0.072 (2)	0.587 (11)
C13X	0.2557 (15)	1.136 (2)	−0.2096 (5)	0.060 (4)	0.413 (11)
H13B	0.3305	1.0955	−0.2267	0.072*	0.413 (11)
C14X	0.1599 (14)	1.2180 (19)	−0.2623 (9)	0.058 (3)	0.413 (11)
H14B	0.1533	1.2220	−0.3233	0.070*	0.413 (11)
C15X	0.0807 (19)	1.2883 (19)	−0.2115 (8)	0.079 (4)	0.413 (11)
H15B	0.0241	1.3695	−0.2263	0.095*	0.413 (11)
O3X	0.1028 (10)	1.212 (2)	−0.1327 (7)	0.078 (4)	0.413 (11)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0494 (8)	0.0629 (8)	0.0569 (10)	−0.0070 (7)	0.0048 (7)	−0.0151 (7)
O2	0.0469 (8)	0.0640 (9)	0.0518 (9)	0.0075 (7)	0.0087 (7)	0.0015 (7)
N1	0.0495 (10)	0.0503 (9)	0.0598 (12)	0.0080 (8)	0.0091 (9)	−0.0036 (8)
N2	0.0456 (9)	0.0460 (9)	0.0478 (10)	0.0066 (7)	0.0073 (8)	0.0019 (7)
C1	0.0492 (12)	0.0482 (11)	0.0430 (12)	0.0013 (9)	0.0049 (9)	0.0042 (9)
C2	0.0586 (14)	0.0577 (13)	0.0655 (15)	0.0065 (11)	0.0072 (11)	0.0096 (11)
C3	0.0848 (18)	0.0643 (15)	0.094 (2)	0.0285 (14)	0.0197 (15)	0.0189 (14)
C4	0.117 (2)	0.0473 (14)	0.112 (2)	0.0000 (16)	0.020 (2)	0.0009 (14)
C5	0.095 (2)	0.0573 (15)	0.118 (3)	−0.0145 (14)	−0.0025 (18)	−0.0073 (15)
C6	0.0640 (15)	0.0533 (13)	0.0916 (19)	−0.0053 (11)	−0.0059 (13)	−0.0008 (12)
C7	0.0431 (11)	0.0502 (11)	0.0433 (12)	−0.0004 (9)	0.0034 (9)	−0.0034 (9)
C8	0.0566 (13)	0.0637 (13)	0.0514 (13)	0.0015 (10)	0.0109 (10)	−0.0045 (10)
C9	0.0485 (12)	0.0564 (12)	0.0592 (15)	0.0021 (10)	0.0083 (11)	−0.0080 (11)
C10	0.0691 (16)	0.1043 (19)	0.0746 (18)	0.0238 (14)	0.0214 (13)	−0.0108 (14)
C11	0.0408 (11)	0.0404 (10)	0.0495 (13)	−0.0054 (9)	0.0034 (9)	−0.0008 (9)
C12	0.0458 (12)	0.0492 (12)	0.0540 (14)	−0.0057 (10)	0.0041 (10)	0.0066 (10)
C13	0.063 (5)	0.076 (5)	0.075 (7)	0.026 (4)	0.016 (4)	0.030 (5)
C14	0.070 (7)	0.082 (6)	0.060 (6)	0.034 (5)	−0.006 (5)	0.013 (6)
C15	0.062 (7)	0.118 (10)	0.050 (4)	−0.013 (4)	0.009 (4)	0.022 (5)
O3	0.075 (3)	0.082 (6)	0.057 (3)	−0.007 (2)	−0.001 (2)	0.0081 (18)
C13X	0.075 (7)	0.050 (6)	0.061 (8)	0.000 (4)	0.032 (7)	0.006 (4)
C14X	0.062 (12)	0.065 (8)	0.051 (6)	0.005 (7)	0.016 (5)	0.011 (5)
C15X	0.106 (9)	0.073 (7)	0.059 (7)	0.033 (5)	0.009 (6)	0.010 (6)
O3X	0.066 (5)	0.100 (7)	0.067 (5)	0.015 (4)	0.003 (4)	0.038 (4)

Geometric parameters (Å, º) top

O1—C7	1.398 (2)	C8—H8B	0.9700
O1—H1	0.8200	C9—C10	1.493 (3)
O2—C11	1.232 (2)	C10—H10A	0.9600
N1—C9	1.277 (2)	C10—H10B	0.9600
N1—N2	1.401 (2)	C10—H10C	0.9600
N2—C11	1.352 (2)	C11—C12	1.457 (2)
N2—C7	1.492 (2)	C12—C13X	1.3407 (11)
C1—C2	1.370 (3)	C12—C13	1.3407 (10)
C1—C6	1.380 (3)	C12—O3	1.3670 (10)
C1—C7	1.516 (3)	C12—O3X	1.3677 (10)
C2—C3	1.390 (3)	C13—C14	1.4230 (11)
C2—H2	0.9300	C13—H13A	0.9300
C3—C4	1.363 (3)	C14—C15	1.3407 (10)
C3—H3	0.9300	C14—H14A	0.9300
C4—C5	1.355 (4)	C15—O3	1.3679 (10)
C4—H4	0.9300	C15—H15A	0.9300
C5—C6	1.374 (3)	C13X—C14X	1.4230 (10)
C5—H5	0.9300	C13X—H13B	0.9300
C6—H6	0.9300	C14X—C15X	1.3406 (10)
C7—C8	1.536 (3)	C14X—H14B	0.9300
C8—C9	1.486 (3)	C15X—O3X	1.3679 (10)
C8—H8A	0.9700	C15X—H15B	0.9300

C7—O1—H1	109.5	C9—C10—H10A	109.5
C9—N1—N2	107.11 (16)	C9—C10—H10B	109.5
C11—N2—N1	123.00 (16)	H10A—C10—H10B	109.5
C11—N2—C7	122.41 (15)	C9—C10—H10C	109.5
N1—N2—C7	113.55 (15)	H10A—C10—H10C	109.5
C2—C1—C6	118.50 (19)	H10B—C10—H10C	109.5
C2—C1—C7	121.90 (18)	O2—C11—N2	118.98 (17)
C6—C1—C7	119.60 (17)	O2—C11—C12	120.23 (17)
C1—C2—C3	120.2 (2)	N2—C11—C12	120.77 (16)
C1—C2—H2	119.9	C13X—C12—C13	98.3 (7)
C3—C2—H2	119.9	C13—C12—O3	110.4 (5)
C4—C3—C2	120.5 (2)	C13X—C12—O3X	108.3 (7)
C4—C3—H3	119.8	O3—C12—O3X	119.0 (6)
C2—C3—H3	119.8	C13X—C12—C11	125.7 (6)
C5—C4—C3	119.5 (2)	C13—C12—C11	135.6 (4)
C5—C4—H4	120.3	O3—C12—C11	114.0 (4)
C3—C4—H4	120.3	O3X—C12—C11	126.0 (5)
C4—C5—C6	120.7 (2)	C12—C13—C14	104.7 (6)
C4—C5—H5	119.6	C12—C13—H13A	127.7
C6—C5—H5	119.6	C14—C13—H13A	127.7
C5—C6—C1	120.7 (2)	C15—C14—C13	108.8 (9)
C5—C6—H6	119.7	C15—C14—H14A	125.6
C1—C6—H6	119.7	C13—C14—H14A	125.6
O1—C7—N2	110.47 (15)	C14—C15—O3	107.5 (8)
O1—C7—C1	114.13 (15)	C14—C15—H15A	126.3
N2—C7—C1	110.34 (15)	O3—C15—H15A	126.3
O1—C7—C8	106.70 (15)	C12—O3—C15	107.6 (7)
N2—C7—C8	99.82 (14)	C12—C13X—C14X	104.4 (8)
C1—C7—C8	114.43 (16)	C12—C13X—H13B	127.8
C9—C8—C7	103.87 (17)	C14X—C13X—H13B	127.8
C9—C8—H8A	111.0	C15X—C14X—C13X	110.3 (13)
C7—C8—H8A	111.0	C15X—C14X—H14B	124.8
C9—C8—H8B	111.0	C13X—C14X—H14B	124.8
C7—C8—H8B	111.0	C14X—C15X—O3X	103.6 (11)
H8A—C8—H8B	109.0	C14X—C15X—H15B	128.2
N1—C9—C8	114.99 (17)	O3X—C15X—H15B	128.2
N1—C9—C10	121.0 (2)	C12—O3X—C15X	110.2 (10)
C8—C9—C10	124.0 (2)

C9—N1—N2—C11	−173.27 (17)	C7—N2—C11—C12	−175.89 (16)
C9—N1—N2—C7	−4.7 (2)	O2—C11—C12—C13X	−0.8 (13)
C6—C1—C2—C3	0.0 (3)	N2—C11—C12—C13X	−179.1 (12)
C7—C1—C2—C3	179.19 (19)	O2—C11—C12—C13	−171.2 (12)
C1—C2—C3—C4	−0.7 (4)	N2—C11—C12—C13	10.5 (13)
C2—C3—C4—C5	0.7 (4)	O2—C11—C12—O3	8.7 (6)
C3—C4—C5—C6	−0.1 (4)	N2—C11—C12—O3	−169.6 (5)
C4—C5—C6—C1	−0.6 (4)	O2—C11—C12—O3X	177.3 (10)
C2—C1—C6—C5	0.6 (3)	N2—C11—C12—O3X	−1.0 (11)
C7—C1—C6—C5	−178.6 (2)	C13X—C12—C13—C14	13.4 (15)
C11—N2—C7—O1	64.3 (2)	O3—C12—C13—C14	5.6 (16)
N1—N2—C7—O1	−104.43 (16)	O3X—C12—C13—C14	−128 (6)
C11—N2—C7—C1	−62.9 (2)	C11—C12—C13—C14	−174.5 (6)
N1—N2—C7—C1	128.44 (15)	C12—C13—C14—C15	−9.9 (18)
C11—N2—C7—C8	176.34 (16)	C13—C14—C15—O3	10.3 (19)
N1—N2—C7—C8	7.66 (18)	C13X—C12—O3—C15	−33 (5)
C2—C1—C7—O1	3.3 (3)	C13—C12—O3—C15	0.5 (15)
C6—C1—C7—O1	−177.48 (18)	O3X—C12—O3—C15	11.1 (13)
C2—C1—C7—N2	128.39 (19)	C11—C12—O3—C15	−179.5 (9)
C6—C1—C7—N2	−52.4 (2)	C14—C15—O3—C12	−6.8 (17)
C2—C1—C7—C8	−120.0 (2)	C13—C12—C13X—C14X	−11.5 (17)
C6—C1—C7—C8	59.2 (2)	O3—C12—C13X—C14X	137 (6)
O1—C7—C8—C9	107.68 (17)	O3X—C12—C13X—C14X	−3 (2)
N2—C7—C8—C9	−7.31 (18)	C11—C12—C13X—C14X	175.3 (9)
C1—C7—C8—C9	−125.09 (17)	C12—C13X—C14X—C15X	14 (2)
N2—N1—C9—C8	−0.9 (2)	C13X—C14X—C15X—O3X	−18 (2)
N2—N1—C9—C10	179.00 (18)	C13X—C12—O3X—C15X	−8 (2)
C7—C8—C9—N1	5.7 (2)	C13—C12—O3X—C15X	32 (5)
C7—C8—C9—C10	−174.22 (19)	O3—C12—O3X—C15X	−18.4 (19)
N1—N2—C11—O2	173.43 (16)	C11—C12—O3X—C15X	173.5 (11)
C7—N2—C11—O2	5.8 (2)	C14X—C15X—O3X—C12	16 (2)
N1—N2—C11—C12	−8.3 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2ⁱ	0.82	2.02	2.7786 (18)	153
C14—H14A···O1ⁱⁱ	0.93	2.36	3.271 (9)	168

Symmetry codes: (i) −x+1, −y+2, −z; (ii) x−1/2, −y+5/2, z−1/2.

Experimental details

Crystal data
Chemical formula	C₁₅H₁₄N₂O₃
M_r	270.28
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	296
a, b, c (Å)	10.6844 (10), 8.4700 (7), 15.3022 (16)
β (°)	95.266 (3)
V (Å³)	1379.0 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.28 × 0.22 × 0.16

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.975, 0.985
No. of measured, independent and observed [I > 2σ(I)] reflections	10534, 2495, 1615
R_int	0.044
(sin θ/λ)_max (Å⁻¹)	0.600

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.106, 1.03
No. of reflections	2495
No. of parameters	221
No. of restraints	10
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.12, −0.13

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2ⁱ	0.82	2.02	2.7786 (18)	153
C14—H14A···O1ⁱⁱ	0.93	2.36	3.271 (9)	168

Symmetry codes: (i) −x+1, −y+2, −z; (ii) x−1/2, −y+5/2, z−1/2.

Acknowledgements

HK thanks PNU for financial support. RK thanks the Science and Branch, Islamic Azad University. MM thanks the University of Isfahan for the facilities and MNT thanks the University of Sargodha for the research facilities.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CrossRef Web of Science Google Scholar
Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 67| Part 2| February 2011| Page o367

doi:10.1107/S1600536811000948

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

(Furan-2-yl)(5-hy­dr­oxy-3-methyl-5-phenyl-4,5-di­hydro-1H-pyrazol-1-yl)methanone

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

(Furan-2-yl)(5-hydroxy-3-methyl-5-phenyl-4,5-dihydro-1H-pyrazol-1-yl)methanone