4-Hydroxy-phenyl 4-fluoro-benzoate.

In the title compound, C(13)H(9)FO(3), the dihedral angle between the two benzene rings is 59.86 (4)°. In the crystal, inter-molecular O-H⋯H hydrogen bonds lead to molecular chains propagating in [010].

Related literature

For general background to whitening agents, see: Ha et al. (2007 ▶); Dawley et al. (1993 ▶); Nerya et al. (2003 ▶); Hong et al. (2008 ▶); Lee et al. (2007 ▶); Hussain et al. (2003 ▶).

Experimental

Crystal data

C13H9FO3

M = 232.2

Monoclinic,

a = 24.938 (5) Å

b = 5.4789 (11) Å

c = 7.6858 (15) Å

β = 93.59 (3)°

V = 1048.1 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.12 mm−1

T = 174 (2) K

0.12 × 0.09 × 0.06 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: none

10972 measured reflections

2597 independent reflections

2054 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.105

S = 1.05

2597 reflections

158 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.31 e Å−3

Δρmin = −0.24 e Å−3

Data collection: SMART (Bruker, 2002 ▶); cell refinement: SAINT (Bruker, 2002 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809000129/bh2214sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809000129/bh2214Isup2.hkl

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

C13H9FO3	F(000) = 480
Mr = 232.2	Dx = 1.472 Mg m−3
Monoclinic, P21/c	Melting point: 454 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 24.938 (5) Å	Cell parameters from 3698 reflections
b = 5.4789 (11) Å	θ = 2.5–28.0°
c = 7.6858 (15) Å	µ = 0.12 mm−1
β = 93.59 (3)°	T = 174 K
V = 1048.1 (4) Å3	Block, colourless
Z = 4	0.12 × 0.09 × 0.06 mm

Bruker SMART CCD area-detector diffractometer	Rint = 0.027
φ and ω scans	θmax = 28.3°, θmin = 0.8°
10972 measured reflections	h = −31→33
2597 independent reflections	k = −6→7
2054 reflections with I > 2σ(I)	l = −10→10

Refinement on F2	0 restraints
Least-squares matrix: full	0 constraints
R[F2 > 2σ(F2)] = 0.041	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.105	w = 1/[σ2(Fo2) + (0.0431P)2 + 0.436P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max < 0.001
2597 reflections	Δρmax = 0.31 e Å−3
158 parameters	Δρmin = −0.24 e Å−3

	x	y	z	Uiso*/Ueq
C1	0.17529 (5)	0.4464 (2)	0.47353 (17)	0.0219 (3)
C2	0.13428 (5)	0.2841 (3)	0.50782 (18)	0.0249 (3)
H2	0.1423	0.1423	0.5708	0.03*
C3	0.08163 (6)	0.3318 (3)	0.44905 (19)	0.0275 (3)
H3	0.0541	0.224	0.4711	0.033*
C4	0.07154 (5)	0.5443 (3)	0.35679 (18)	0.0270 (3)
C5	0.11101 (6)	0.7093 (3)	0.32085 (18)	0.0278 (3)
H5	0.1026	0.8508	0.2581	0.033*
C6	0.16347 (6)	0.6597 (3)	0.38026 (17)	0.0250 (3)
H6	0.1908	0.7688	0.3579	0.03*
C7	0.23063 (5)	0.3826 (3)	0.54191 (18)	0.0259 (3)
O8	0.24211 (4)	0.2045 (2)	0.62716 (18)	0.0523 (4)
O9	0.26681 (4)	0.55210 (17)	0.49833 (12)	0.0243 (2)
C10	0.32036 (5)	0.5229 (2)	0.56439 (16)	0.0207 (3)
C11	0.35119 (5)	0.3277 (2)	0.51648 (16)	0.0229 (3)
H11	0.3364	0.2065	0.4436	0.027*
C12	0.40460 (5)	0.3149 (2)	0.57859 (17)	0.0226 (3)
H12	0.426	0.1849	0.5474	0.027*
C13	0.42597 (5)	0.4975 (2)	0.68769 (17)	0.0215 (3)
C14	0.39464 (5)	0.6938 (2)	0.73353 (17)	0.0234 (3)
H14	0.4093	0.8157	0.806	0.028*
C15	0.34135 (5)	0.7073 (2)	0.67088 (17)	0.0225 (3)
H15	0.32	0.8385	0.7001	0.027*
O16	0.47887 (4)	0.4939 (2)	0.75328 (14)	0.0302 (3)
H16	0.4915 (8)	0.356 (4)	0.742 (3)	0.052 (6)*
F17	0.02021 (3)	0.59316 (18)	0.29800 (13)	0.0424 (3)

	U11	U22	U33	U12	U13	U23
C1	0.0203 (6)	0.0223 (7)	0.0231 (6)	0.0016 (5)	0.0006 (5)	−0.0004 (5)
C2	0.0238 (7)	0.0220 (7)	0.0289 (7)	0.0006 (5)	0.0015 (5)	0.0022 (5)
C3	0.0209 (7)	0.0267 (7)	0.0349 (7)	−0.0026 (6)	0.0016 (5)	−0.0021 (6)
C4	0.0198 (7)	0.0289 (7)	0.0317 (7)	0.0047 (6)	−0.0043 (5)	−0.0060 (6)
C5	0.0295 (7)	0.0230 (7)	0.0302 (7)	0.0045 (6)	−0.0035 (5)	0.0010 (5)
C6	0.0249 (7)	0.0227 (7)	0.0273 (7)	−0.0019 (5)	0.0005 (5)	0.0011 (5)
C7	0.0208 (7)	0.0285 (7)	0.0284 (7)	0.0003 (6)	0.0017 (5)	0.0061 (6)
O8	0.0238 (6)	0.0539 (8)	0.0787 (9)	0.0006 (5)	−0.0009 (6)	0.0418 (7)
O9	0.0185 (5)	0.0237 (5)	0.0300 (5)	−0.0015 (4)	−0.0038 (4)	0.0041 (4)
C10	0.0169 (6)	0.0239 (7)	0.0210 (6)	−0.0009 (5)	−0.0015 (5)	0.0036 (5)
C11	0.0255 (7)	0.0206 (7)	0.0224 (6)	−0.0028 (5)	−0.0003 (5)	−0.0013 (5)
C12	0.0225 (7)	0.0202 (6)	0.0252 (6)	0.0020 (5)	0.0024 (5)	−0.0001 (5)
C13	0.0174 (6)	0.0231 (7)	0.0237 (6)	−0.0021 (5)	0.0003 (5)	0.0038 (5)
C14	0.0242 (7)	0.0209 (7)	0.0248 (6)	−0.0032 (5)	−0.0013 (5)	−0.0034 (5)
C15	0.0225 (7)	0.0206 (6)	0.0245 (6)	0.0019 (5)	0.0027 (5)	−0.0012 (5)
O16	0.0186 (5)	0.0288 (6)	0.0423 (6)	0.0007 (4)	−0.0052 (4)	−0.0018 (4)
F17	0.0223 (5)	0.0426 (6)	0.0605 (6)	0.0056 (4)	−0.0106 (4)	0.0019 (5)

C1—C2	1.3928 (19)	O9—C10	1.4078 (15)
C1—C6	1.3932 (18)	C10—C11	1.3806 (19)
C1—C7	1.4872 (18)	C10—C15	1.3824 (18)
C2—C3	1.3863 (19)	C11—C12	1.3881 (18)
C2—H2	0.93	C11—H11	0.93
C3—C4	1.378 (2)	C12—C13	1.3900 (18)
C3—H3	0.93	C12—H12	0.93
C4—F17	1.3572 (15)	C13—O16	1.3826 (16)
C4—C5	1.377 (2)	C13—C14	1.3874 (19)
C5—C6	1.3854 (19)	C14—C15	1.3869 (18)
C5—H5	0.93	C14—H14	0.93
C6—H6	0.93	C15—H15	0.93
C7—O8	1.2000 (17)	O16—H16	0.82 (2)
C7—O9	1.3514 (17)
C2—C1—C6	119.93 (12)	C7—O9—C10	117.74 (10)
C2—C1—C7	117.35 (12)	C11—C10—C15	121.83 (12)
C6—C1—C7	122.72 (12)	C11—C10—O9	121.57 (12)
C3—C2—C1	120.65 (13)	C15—C10—O9	116.47 (12)
C3—C2—H2	119.7	C10—C11—C12	119.06 (12)
C1—C2—H2	119.7	C10—C11—H11	120.5
C4—C3—C2	117.74 (13)	C12—C11—H11	120.5
C4—C3—H3	121.1	C11—C12—C13	119.64 (12)
C2—C3—H3	121.1	C11—C12—H12	120.2
F17—C4—C5	118.34 (13)	C13—C12—H12	120.2
F17—C4—C3	118.43 (13)	O16—C13—C14	117.27 (12)
C5—C4—C3	123.23 (13)	O16—C13—C12	122.04 (12)
C4—C5—C6	118.52 (13)	C14—C13—C12	120.68 (12)
C4—C5—H5	120.7	C15—C14—C13	119.72 (12)
C6—C5—H5	120.7	C15—C14—H14	120.1
C5—C6—C1	119.93 (13)	C13—C14—H14	120.1
C5—C6—H6	120	C10—C15—C14	119.05 (12)
C1—C6—H6	120	C10—C15—H15	120.5
O8—C7—O9	123.63 (13)	C14—C15—H15	120.5
O8—C7—C1	124.63 (13)	C13—O16—H16	109.7 (14)
O9—C7—C1	111.73 (11)

D—H···A	D—H	H···A	D···A	D—H···A
O16—H16···O16i	0.82 (2)	2.12 (2)	2.9368 (9)	172 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O16—H16⋯O16i	0.82 (2)	2.12 (2)	2.9368 (9)	172 (2)

Symmetry code: (i) .