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

In the title compound, C(15)H(14)N(2)O(3), 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 mol-ecule shows chirality in one of the carbon atoms but the centrosymmetric space group means the compound is a racemic mixture. In the crystal, inter-molecular O-H⋯O and C-H⋯O hydrogen bonds connect the mol-ecules. The crystal structure is further stabilized by π-π stacking inter-actions 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 = 270.28

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.106

S = 1.03

2495 reflections

221 parameters

10 restraints

H-atom parameters constrained

Δρmax = 0.12 e Å−3

Δρmin = −0.13 e Å−3

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 ▶).

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

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

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

C15H14N2O3	F(000) = 568
Mr = 270.28	Dx = 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

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

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(Fo2) + (0.037P)2 + 0.1913P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max < 0.001
2495 reflections	Δρmax = 0.12 e Å−3
221 parameters	Δρmin = −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)

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.

	x	y	z	Uiso*/Ueq	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)

	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)

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)

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

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) ; (ii) .