1-(4-Fluoro-phen-yl)-3-hydr-oxy-3-phenyl-prop-2-en-1-one.

In the crystal structure the title compound, C(15)H(11)FO(2), the molecule exists in the enol form. It is stabilized by an intra-molecular O-H⋯O hydrogen bond, in which the donor O-H and acceptor H⋯O distances are almost equal. The dihedral angle between the two benzene rings is 22.30 (4)°.

Related literature

For background to the uses and characteristics of 1,3-diketones, see: Gilli et al. (2004 ▶); Hasegawa et al. (1997 ▶); Jang et al. (2006 ▶); Ma et al. (1999 ▶); Yoshida et al. (2005 ▶). For geometric data, see: Bertolasi et al. (1991 ▶); Wang et al. (2006 ▶).

Experimental

Crystal data

C15H11FO2

M = 242.24

Monoclinic,

a = 11.8526 (5) Å

b = 11.7192 (5) Å

c = 9.4164 (4) Å

β = 113.405 (1)°

V = 1200.35 (9) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 298 K

0.30 × 0.10 × 0.04 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.991, T max = 0.996

11206 measured reflections

2109 independent reflections

1295 reflections with I > 2σ(I)

R int = 0.106

Refinement

R[F 2 > 2σ(F 2)] = 0.051

wR(F 2) = 0.140

S = 0.93

2109 reflections

166 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.25 e Å−3

Δρmin = −0.19 e Å−3

Data collection: SMART (Bruker, 1997 ▶); cell refinement: SAINT (Bruker, 1999 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809004747/kj2112sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809004747/kj2112Isup2.hkl

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

C15H11FO2	F(000) = 504
Mr = 242.24	Dx = 1.340 Mg m−3
Monoclinic, P21/c	Melting point: 351 K
Hall symbol: -P2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 11.8526 (5) Å	Cell parameters from 2616 reflections
b = 11.7192 (5) Å	θ = 2.6–22.7°
c = 9.4164 (4) Å	µ = 0.10 mm−1
β = 113.405 (1)°	T = 298 K
V = 1200.35 (9) Å3	Plate, colourless
Z = 4	0.30 × 0.10 × 0.04 mm

Bruker SMART CCD area-detector diffractometer	2109 independent reflections
Radiation source: fine-focus sealed tube	1295 reflections with I > 2σ(I)
graphite	Rint = 0.106
φ and ω scans	θmax = 25.0°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −14→14
Tmin = 0.991, Tmax = 0.996	k = −13→13
11206 measured reflections	l = −11→11

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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.140	H atoms treated by a mixture of independent and constrained refinement
S = 0.93	w = 1/[σ2(Fo2) + (0.0849P)2] where P = (Fo2 + 2Fc2)/3
2109 reflections	(Δ/σ)max < 0.001
166 parameters	Δρmax = 0.25 e Å−3
0 restraints	Δρmin = −0.19 e Å−3

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
C1	0.27135 (19)	0.29172 (18)	0.4883 (2)	0.0742 (6)
C2	0.29882 (19)	0.17926 (17)	0.4841 (2)	0.0804 (6)
H2	0.2565	0.1236	0.5136	0.096*
C3	0.38951 (19)	0.14902 (16)	0.4358 (2)	0.0753 (6)
H3	0.4082	0.0722	0.4329	0.090*
C4	0.45487 (16)	0.23125 (14)	0.39078 (19)	0.0600 (5)
C5	0.42305 (18)	0.34513 (15)	0.3965 (2)	0.0694 (6)
H5	0.4645	0.4018	0.3673	0.083*
C6	0.33131 (19)	0.37574 (17)	0.4446 (2)	0.0781 (6)
H6	0.3106	0.4520	0.4473	0.094*
C7	0.55320 (17)	0.19568 (14)	0.3396 (2)	0.0634 (5)
C8	0.63154 (16)	0.27122 (14)	0.3102 (2)	0.0627 (5)
H8	0.6220	0.3491	0.3208	0.075*
C9	0.72513 (17)	0.23318 (15)	0.2648 (2)	0.0664 (5)
C10	0.81581 (16)	0.30949 (15)	0.2408 (2)	0.0635 (5)
C11	0.8874 (2)	0.26895 (18)	0.1647 (2)	0.0811 (6)
H11	0.8778	0.1941	0.1291	0.097*
C12	0.9732 (2)	0.3393 (2)	0.1414 (3)	0.0959 (7)
H12	1.0190	0.3116	0.0883	0.115*
C13	0.99055 (19)	0.4487 (2)	0.1958 (3)	0.0909 (7)
H13	1.0486	0.4952	0.1811	0.109*
C14	0.92093 (19)	0.48972 (18)	0.2731 (2)	0.0901 (7)
H14	0.9329	0.5639	0.3112	0.108*
C15	0.83398 (19)	0.42134 (17)	0.2941 (2)	0.0781 (6)
H15	0.7869	0.4505	0.3445	0.094*
F1	0.18286 (12)	0.32154 (11)	0.53824 (16)	0.1081 (5)
O1	0.56461 (14)	0.08669 (11)	0.32400 (18)	0.0923 (5)
O2	0.73642 (15)	0.12538 (11)	0.24314 (19)	0.0931 (5)
H2A	0.650 (2)	0.087 (2)	0.270 (3)	0.140*

	U11	U22	U33	U12	U13	U23
C1	0.0767 (13)	0.0819 (14)	0.0718 (13)	−0.0013 (11)	0.0378 (11)	0.0039 (10)
C2	0.0866 (15)	0.0725 (14)	0.0856 (15)	−0.0167 (11)	0.0379 (12)	0.0098 (11)
C3	0.0870 (14)	0.0523 (12)	0.0853 (14)	−0.0058 (10)	0.0329 (12)	0.0056 (9)
C4	0.0695 (11)	0.0483 (10)	0.0548 (11)	−0.0051 (8)	0.0170 (9)	0.0040 (8)
C5	0.0849 (14)	0.0483 (11)	0.0837 (14)	−0.0008 (9)	0.0428 (11)	0.0040 (9)
C6	0.0959 (15)	0.0591 (12)	0.0938 (15)	0.0021 (10)	0.0530 (13)	0.0009 (10)
C7	0.0750 (12)	0.0442 (10)	0.0667 (12)	0.0046 (9)	0.0235 (10)	0.0011 (8)
C8	0.0714 (12)	0.0430 (10)	0.0733 (12)	0.0053 (8)	0.0284 (10)	−0.0035 (8)
C9	0.0777 (13)	0.0523 (11)	0.0640 (12)	0.0101 (9)	0.0227 (10)	−0.0037 (9)
C10	0.0660 (12)	0.0605 (12)	0.0621 (11)	0.0125 (9)	0.0236 (9)	−0.0006 (9)
C11	0.0863 (14)	0.0781 (14)	0.0830 (15)	0.0148 (12)	0.0380 (12)	−0.0110 (11)
C12	0.0910 (16)	0.114 (2)	0.0986 (18)	0.0141 (14)	0.0549 (15)	−0.0037 (14)
C13	0.0850 (15)	0.0948 (17)	0.0980 (17)	0.0036 (13)	0.0418 (14)	0.0061 (13)
C14	0.0968 (15)	0.0715 (13)	0.1198 (19)	−0.0030 (11)	0.0617 (15)	−0.0042 (12)
C15	0.0875 (14)	0.0619 (12)	0.1025 (16)	0.0039 (10)	0.0562 (13)	−0.0060 (11)
F1	0.1104 (10)	0.1162 (11)	0.1240 (11)	−0.0001 (8)	0.0742 (9)	0.0031 (8)
O1	0.1175 (12)	0.0406 (8)	0.1328 (13)	0.0027 (7)	0.0647 (10)	−0.0009 (7)
O2	0.1094 (12)	0.0522 (8)	0.1332 (13)	0.0088 (7)	0.0645 (11)	−0.0136 (8)

C1—F1	1.354 (2)	C8—H8	0.9300
C1—C2	1.362 (3)	C9—C10	1.483 (3)
C1—C6	1.370 (3)	C10—C15	1.389 (3)
C2—C3	1.369 (3)	C10—C11	1.393 (3)
C2—H2	0.9300	C11—C12	1.393 (3)
C3—C4	1.404 (3)	C11—H11	0.9300
C3—H3	0.9300	C12—C13	1.365 (3)
C4—C5	1.394 (2)	C12—H12	0.9300
C4—C7	1.487 (3)	C13—C14	1.386 (3)
C5—C6	1.381 (3)	C13—H13	0.9300
C5—H5	0.9300	C14—C15	1.380 (3)
C6—H6	0.9300	C14—H14	0.9300
O1—C7	1.299 (2)	C15—H15	0.9300
O2—C9	1.295 (2)	O1—H2A	1.30 (3)
C7—C8	1.388 (2)	O2—H2A	1.23 (3)
C8—C9	1.410 (3)
F1—C1—C2	119.14 (18)	O2—C9—C8	119.94 (18)
F1—C1—C6	118.98 (18)	O2—C9—C10	115.95 (17)
C2—C1—C6	121.88 (18)	C8—C9—C10	124.11 (16)
C1—C2—C3	119.24 (18)	C15—C10—C11	117.95 (18)
C1—C2—H2	120.4	C15—C10—C9	122.10 (16)
C3—C2—H2	120.4	C11—C10—C9	119.94 (17)
C2—C3—C4	121.53 (19)	C12—C11—C10	120.73 (19)
C2—C3—H3	119.2	C12—C11—H11	119.6
C4—C3—H3	119.2	C10—C11—H11	119.6
C5—C4—C3	117.09 (18)	C13—C12—C11	120.5 (2)
C5—C4—C7	122.68 (16)	C13—C12—H12	119.8
C3—C4—C7	120.22 (17)	C11—C12—H12	119.8
C6—C5—C4	121.45 (18)	C12—C13—C14	119.4 (2)
C6—C5—H5	119.3	C12—C13—H13	120.3
C4—C5—H5	119.3	C14—C13—H13	120.3
C1—C6—C5	118.82 (18)	C15—C14—C13	120.5 (2)
C1—C6—H6	120.6	C15—C14—H14	119.7
C5—C6—H6	120.6	C13—C14—H14	119.7
O1—C7—C8	119.79 (17)	C14—C15—C10	120.90 (18)
O1—C7—C4	116.27 (16)	C14—C15—H15	119.5
C8—C7—C4	123.94 (15)	C10—C15—H15	119.5
C7—C8—C9	121.86 (16)	C7—O1—H2A	99.8 (11)
C7—C8—H8	119.1	C9—O2—H2A	100.1 (12)
C9—C8—H8	119.1
F1—C1—C2—C3	−179.05 (18)	C4—C7—C8—C9	178.70 (16)
C6—C1—C2—C3	0.5 (3)	C7—C8—C9—O2	2.9 (3)
C1—C2—C3—C4	0.0 (3)	C7—C8—C9—C10	−176.33 (17)
C2—C3—C4—C5	−0.3 (3)	O2—C9—C10—C15	−164.43 (17)
C2—C3—C4—C7	179.74 (17)	C8—C9—C10—C15	14.9 (3)
C3—C4—C5—C6	0.1 (3)	O2—C9—C10—C11	14.5 (3)
C7—C4—C5—C6	−179.97 (17)	C8—C9—C10—C11	−166.16 (17)
F1—C1—C6—C5	178.82 (17)	C15—C10—C11—C12	−0.8 (3)
C2—C1—C6—C5	−0.7 (3)	C9—C10—C11—C12	−179.86 (19)
C4—C5—C6—C1	0.4 (3)	C10—C11—C12—C13	1.5 (3)
C5—C4—C7—O1	−172.91 (17)	C11—C12—C13—C14	−0.8 (4)
C3—C4—C7—O1	7.0 (2)	C12—C13—C14—C15	−0.6 (4)
C5—C4—C7—C8	7.8 (3)	C13—C14—C15—C10	1.2 (3)
C3—C4—C7—C8	−172.31 (18)	C11—C10—C15—C14	−0.5 (3)
O1—C7—C8—C9	−0.6 (3)	C9—C10—C15—C14	178.53 (19)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2A···O1	1.23 (3)	1.30 (3)	2.4827 (19)	157 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2A⋯O1	1.23 (3)	1.30 (3)	2.4827 (19)	157 (2)