(E)-4-(4-Fluoro-styr-yl)benzoic acid.

The title compound, C(15)H(11)FO(2), is an important inter-mediate in the synthesis of side-chain ligands for polymeric liquid crystals. The vinyl group is almost coplanar with both the aromatic rings. The crystal structure is stabilized by inter-molecular O-H⋯O hydrogen bonding.

Related literature

For related literature, see: Ahmad et al. (2003 ▶); Collings & Hird (1997 ▶); Frazee & Foraker (2008 ▶); Hameed & Rama (2004 ▶); Hussain et al. (2005 ▶); Nazir et al. (2008 ▶); Ribeiro et al. (2008 ▶); Wang et al. (2008 ▶); Higashi (1999 ▶); Yasuda et al. (2000 ▶).

Experimental

Crystal data

C15H11FO2

M = 242.24

Monoclinic,

a = 6.261 (4) Å

b = 23.096 (15) Å

c = 8.269 (5) Å

β = 107.072 (8)°

V = 1143.1 (13) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 123 (2) K

0.45 × 0.30 × 0.18 mm

Data collection

Rigaku/MSC Mercury CCD diffractometer

Absorption correction: none

9111 measured reflections

2589 independent reflections

2399 reflections with I > 2σ(I)

R int = 0.036

Refinement

R[F 2 > 2σ(F 2)] = 0.065

wR(F 2) = 0.155

S = 1.16

2589 reflections

167 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.55 e Å−3

Δρmin = −0.28 e Å−3

Data collection: CrystalClear (MSC/Rigaku, 2001 ▶); cell refinement: CrystalClear; data reduction: TEXSAN (MSC/Rigaku, 2004 ▶); program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEPII (Johnson, 1976 ▶); software used to prepare material for publication: SHELXL97 and TEXSAN.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808012920/hg2398sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808012920/hg2398Isup2.hkl

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

C15H11FO2	F(000) = 504
Mr = 242.24	Dx = 1.408 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71070 Å
Hall symbol: -P 2ybc	Cell parameters from 3252 reflections
a = 6.261 (4) Å	θ = 3.1–27.5°
b = 23.096 (15) Å	µ = 0.10 mm−1
c = 8.269 (5) Å	T = 123 K
β = 107.072 (8)°	Needle, colourless
V = 1143.1 (13) Å3	0.45 × 0.30 × 0.18 mm
Z = 4

Rigaku/MSC Mercury CCD diffractometer	2399 reflections with I > 2σ(I)
Radiation source: Rotating anode	Rint = 0.036
graphite	θmax = 27.5°, θmin = 3.1°
ω scans	h = −8→6
9111 measured reflections	k = −25→29
2589 independent reflections	l = −10→9

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)] = 0.065	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.155	H atoms treated by a mixture of independent and constrained refinement
S = 1.16	w = 1/[σ2(Fo2) + (0.0616P)2 + 0.7669P] where P = (Fo2 + 2Fc2)/3
2589 reflections	(Δ/σ)max < 0.001
167 parameters	Δρmax = 0.55 e Å−3
0 restraints	Δρmin = −0.28 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	0.7742 (3)	0.03235 (7)	0.8139 (2)	0.0188 (4)
O1	0.9748 (2)	0.04569 (6)	0.83715 (16)	0.0268 (3)
O2	0.7095 (2)	−0.00358 (6)	0.90952 (16)	0.0258 (3)
H2	0.843 (6)	−0.0202 (16)	1.006 (5)	0.089 (12)*
C2	0.5982 (3)	0.05820 (7)	0.6720 (2)	0.0188 (4)
C3	0.6547 (3)	0.10173 (8)	0.5755 (2)	0.0221 (4)
H3	0.8054	0.1143	0.6002	0.027*
C4	0.4916 (3)	0.12671 (8)	0.4437 (2)	0.0246 (4)
H4	0.5313	0.1568	0.3796	0.030*
C5	0.2699 (3)	0.10851 (8)	0.4031 (2)	0.0231 (4)
C6	0.2149 (3)	0.06476 (8)	0.5012 (2)	0.0232 (4)
H6	0.0645	0.0519	0.4756	0.028*
C7	0.3771 (3)	0.03999 (8)	0.6354 (2)	0.0213 (4)
H7	0.3374	0.0107	0.7020	0.026*
C8	0.1067 (3)	0.13727 (8)	0.2605 (2)	0.0250 (4)
H8	0.1586	0.1694	0.2111	0.030*
C9	−0.1064 (3)	0.12250 (8)	0.1943 (2)	0.0246 (4)
H9	−0.1587	0.0904	0.2436	0.030*
C10	−0.2687 (3)	0.15134 (8)	0.0517 (2)	0.0224 (4)
C11	−0.2127 (3)	0.19609 (8)	−0.0431 (2)	0.0250 (4)
H11	−0.0628	0.2094	−0.0148	0.030*
C12	−0.3734 (3)	0.22120 (8)	−0.1778 (2)	0.0273 (4)
H12	−0.3353	0.2514	−0.2424	0.033*
C13	−0.5900 (3)	0.20104 (8)	−0.2150 (2)	0.0262 (4)
C14	−0.6531 (3)	0.15774 (8)	−0.1256 (2)	0.0257 (4)
H14	−0.8040	0.1451	−0.1539	0.031*
C15	−0.4898 (3)	0.13277 (8)	0.0075 (2)	0.0241 (4)
H15	−0.5300	0.1023	0.0700	0.029*
F1	−0.7470 (2)	0.22525 (6)	−0.34838 (15)	0.0419 (4)

	U11	U22	U33	U12	U13	U23
C1	0.0185 (8)	0.0204 (8)	0.0175 (8)	0.0011 (6)	0.0052 (6)	−0.0007 (6)
O1	0.0173 (6)	0.0346 (8)	0.0269 (7)	0.0001 (5)	0.0040 (5)	0.0061 (5)
O2	0.0227 (6)	0.0285 (7)	0.0251 (6)	0.0005 (5)	0.0053 (5)	0.0084 (5)
C2	0.0190 (8)	0.0200 (8)	0.0165 (8)	0.0030 (6)	0.0038 (6)	−0.0018 (6)
C3	0.0213 (8)	0.0251 (9)	0.0195 (8)	0.0016 (7)	0.0054 (6)	−0.0001 (6)
C4	0.0267 (9)	0.0253 (9)	0.0219 (8)	0.0031 (7)	0.0073 (7)	0.0034 (7)
C5	0.0246 (9)	0.0249 (9)	0.0175 (8)	0.0057 (7)	0.0029 (7)	−0.0022 (6)
C6	0.0175 (8)	0.0265 (9)	0.0237 (8)	0.0019 (7)	0.0032 (7)	−0.0034 (7)
C7	0.0196 (8)	0.0226 (9)	0.0211 (8)	0.0012 (7)	0.0052 (6)	−0.0003 (6)
C8	0.0238 (9)	0.0262 (9)	0.0234 (8)	0.0025 (7)	0.0045 (7)	0.0031 (7)
C9	0.0264 (9)	0.0248 (9)	0.0221 (8)	0.0011 (7)	0.0062 (7)	0.0004 (7)
C10	0.0220 (9)	0.0243 (9)	0.0187 (8)	0.0044 (7)	0.0028 (6)	−0.0041 (6)
C11	0.0216 (9)	0.0259 (10)	0.0265 (9)	−0.0002 (7)	0.0055 (7)	−0.0057 (7)
C12	0.0347 (10)	0.0217 (9)	0.0265 (9)	0.0025 (8)	0.0104 (8)	0.0006 (7)
C13	0.0280 (9)	0.0233 (9)	0.0215 (8)	0.0116 (7)	−0.0018 (7)	−0.0012 (7)
C14	0.0188 (8)	0.0273 (9)	0.0290 (9)	0.0019 (7)	0.0038 (7)	−0.0072 (7)
C15	0.0260 (9)	0.0229 (9)	0.0232 (8)	0.0013 (7)	0.0067 (7)	−0.0006 (7)
F1	0.0413 (7)	0.0402 (8)	0.0330 (7)	0.0202 (6)	−0.0063 (5)	0.0036 (5)

C1—O1	1.252 (2)	C8—C9	1.330 (3)
C1—O2	1.291 (2)	C8—H8	0.9500
C1—C2	1.479 (2)	C9—C10	1.471 (2)
O2—H2	1.04 (4)	C9—H9	0.9500
C2—C3	1.392 (3)	C10—C15	1.392 (3)
C2—C7	1.393 (3)	C10—C11	1.402 (3)
C3—C4	1.382 (2)	C11—C12	1.390 (3)
C3—H3	0.9500	C11—H11	0.9500
C4—C5	1.394 (3)	C12—C13	1.380 (3)
C4—H4	0.9500	C12—H12	0.9500
C5—C6	1.401 (3)	C13—F1	1.363 (2)
C5—C8	1.473 (2)	C13—C14	1.369 (3)
C6—C7	1.389 (2)	C14—C15	1.389 (3)
C6—H6	0.9500	C14—H14	0.9500
C7—H7	0.9500	C15—H15	0.9500
O1—C1—O2	123.07 (15)	C9—C8—H8	116.9
O1—C1—C2	120.16 (15)	C5—C8—H8	116.9
O2—C1—C2	116.78 (15)	C8—C9—C10	125.99 (18)
C1—O2—H2	112 (2)	C8—C9—H9	117.0
C3—C2—C7	119.79 (15)	C10—C9—H9	117.0
C3—C2—C1	119.41 (16)	C15—C10—C11	118.25 (16)
C7—C2—C1	120.80 (16)	C15—C10—C9	118.07 (17)
C4—C3—C2	120.05 (17)	C11—C10—C9	123.68 (17)
C4—C3—H3	120.0	C12—C11—C10	120.96 (18)
C2—C3—H3	120.0	C12—C11—H11	119.5
C3—C4—C5	121.11 (18)	C10—C11—H11	119.5
C3—C4—H4	119.4	C13—C12—C11	118.08 (18)
C5—C4—H4	119.4	C13—C12—H12	121.0
C4—C5—C6	118.38 (16)	C11—C12—H12	121.0
C4—C5—C8	117.69 (17)	F1—C13—C14	118.85 (18)
C6—C5—C8	123.92 (17)	F1—C13—C12	118.02 (18)
C7—C6—C5	120.88 (17)	C14—C13—C12	123.12 (17)
C7—C6—H6	119.6	C13—C14—C15	118.00 (17)
C5—C6—H6	119.6	C13—C14—H14	121.0
C6—C7—C2	119.77 (17)	C15—C14—H14	121.0
C6—C7—H7	120.1	C14—C15—C10	121.58 (18)
C2—C7—H7	120.1	C14—C15—H15	119.2
C9—C8—C5	126.22 (18)	C10—C15—H15	119.2
O1—C1—C2—C3	−6.5 (2)	C6—C5—C8—C9	−7.2 (3)
O2—C1—C2—C3	173.26 (15)	C5—C8—C9—C10	−179.93 (17)
O1—C1—C2—C7	174.23 (16)	C8—C9—C10—C15	−175.06 (18)
O2—C1—C2—C7	−6.0 (2)	C8—C9—C10—C11	5.5 (3)
C7—C2—C3—C4	−0.1 (3)	C15—C10—C11—C12	−0.1 (3)
C1—C2—C3—C4	−179.31 (16)	C9—C10—C11—C12	179.26 (17)
C2—C3—C4—C5	−1.0 (3)	C10—C11—C12—C13	0.4 (3)
C3—C4—C5—C6	1.1 (3)	C11—C12—C13—F1	−179.25 (16)
C3—C4—C5—C8	−179.83 (16)	C11—C12—C13—C14	0.1 (3)
C4—C5—C6—C7	−0.2 (3)	F1—C13—C14—C15	178.64 (16)
C8—C5—C6—C7	−179.19 (17)	C12—C13—C14—C15	−0.7 (3)
C5—C6—C7—C2	−0.9 (3)	C13—C14—C15—C10	0.9 (3)
C3—C2—C7—C6	1.0 (3)	C11—C10—C15—C14	−0.5 (3)
C1—C2—C7—C6	−179.80 (15)	C9—C10—C15—C14	−179.93 (16)
C4—C5—C8—C9	173.72 (19)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O1i	1.04 (4)	1.57 (4)	2.610 (2)	174 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O1i	1.04 (4)	1.57 (4)	2.610 (2)	174 (3)

Symmetry code: (i) .