4-(4-Propoxybenzo-yloxy)benzoic acid.

The title compound, C(17)H(16)O(5), is an important inter-mediate for the synthesis of side-chain ligands for polymeric liquid crystals. The prop-oxy and benzoic acid groups subtend dihedral angles of 4.36 (6) and 55.35 (6)°, respectively, with the central benzo-yloxy unit. The crystal structure is stabilized by an inter-molecular O-H⋯O hydrogen bond.

Related literature

For related literature, see: Ahmad et al. (2003 ▶); Aranzazu et al. (2006 ▶); Cady et al. (2002 ▶); Hameed & Rama (2004 ▶); Hartung et al. (1997 ▶); Hussain et al. (2003 ▶, 2005 ▶); Kong & Tang (1998 ▶); Nazir et al. (2008a ▶,b ▶); Ribeiro et al. (2008 ▶); Shafiq et al. (2003 ▶, 2005 ▶); Wu & Hsu (2007 ▶); Wu & Lin (2007 ▶).

Experimental

Crystal data

C17H16O5

M = 300.30

Monoclinic,

a = 21.063 (15) Å

b = 5.703 (4) Å

c = 24.437 (18) Å

β = 99.790 (9)°

V = 2893 (3) Å3

Z = 8

Mo Kα radiation

μ = 0.10 mm−1

T = 123 (2) K

0.30 × 0.19 × 0.15 mm

Data collection

Rigaku/MSC Mercury CCD diffractometer

Absorption correction: empirical (NUMABS; Higashi, 1999 ▶) T min = 0.970, T max = 0.985

11426 measured reflections

3297 independent reflections

2824 reflections with I > 2σ(I)

R int = 0.051

Refinement

R[F 2 > 2σ(F 2)] = 0.084

wR(F 2) = 0.146

S = 1.26

3297 reflections

201 parameters

H-atom parameters constrained

Δρmax = 0.29 e Å−3

Δρmin = −0.28 e Å−3

Data collection: CrystalClear (Molecular Structure Corporation & Rigaku, 2001 ▶); cell refinement: CrystalClear; data reduction: TEXSAN (Molecular Structure Corporation & 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/S1600536808016942/hg2407sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808016942/hg2407Isup2.hkl

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

C17H16O5	F(000) = 1264
Mr = 300.30	Dx = 1.379 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71070 Å
Hall symbol: -C 2yc	Cell parameters from 3169 reflections
a = 21.063 (15) Å	θ = 3.4–27.5°
b = 5.703 (4) Å	µ = 0.10 mm−1
c = 24.437 (18) Å	T = 123 K
β = 99.790 (9)°	Rod, colorless
V = 2893 (3) Å3	0.30 × 0.19 × 0.15 mm
Z = 8

Rigaku/MSC Mercury CCD diffractometer	3297 independent reflections
Radiation source: fine-focus sealed tube	2824 reflections with I > 2σ(I)
graphite	Rint = 0.051
ω scans	θmax = 27.5°, θmin = 3.4°
Absorption correction: empirical (using intensity measurements) (NUMABS; Higashi, 1999)	h = −23→27
Tmin = 0.970, Tmax = 0.985	k = −7→5
11426 measured reflections	l = −31→31

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)] = 0.084	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.146	H-atom parameters constrained
S = 1.26	w = 1/[σ2(Fo2) + (0.026P)2 + 6.5341P] where P = (Fo2 + 2Fc2)/3
3297 reflections	(Δ/σ)max < 0.001
201 parameters	Δρmax = 0.29 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	0.12026 (11)	0.2626 (4)	0.39828 (9)	0.0171 (5)
C2	0.15716 (12)	0.4515 (4)	0.42065 (10)	0.0223 (5)
H2	0.1686	0.5699	0.3968	0.027*
C3	0.17771 (13)	0.4698 (4)	0.47766 (10)	0.0229 (5)
H3	0.2030	0.6000	0.4926	0.027*
C4	0.16099 (12)	0.2958 (4)	0.51274 (10)	0.0198 (5)
C5	0.12360 (12)	0.1058 (4)	0.49037 (10)	0.0229 (5)
H5	0.1120	−0.0124	0.5142	0.027*
C6	0.10351 (12)	0.0891 (4)	0.43378 (10)	0.0212 (5)
H6	0.0781	−0.0408	0.4188	0.025*
C7	0.09682 (11)	0.2342 (4)	0.33803 (10)	0.0176 (5)
O1	0.06221 (9)	0.0793 (3)	0.31697 (7)	0.0250 (4)
O2	0.11946 (8)	0.4078 (3)	0.30793 (7)	0.0216 (4)
C8	0.09736 (11)	0.4149 (4)	0.25035 (9)	0.0181 (5)
C9	0.06788 (11)	0.6204 (4)	0.22986 (10)	0.0192 (5)
H9	0.0624	0.7460	0.2542	0.023*
C10	0.04640 (11)	0.6402 (4)	0.17308 (10)	0.0177 (5)
H10	0.0254	0.7794	0.1583	0.021*
C11	0.05562 (11)	0.4570 (4)	0.13782 (10)	0.0169 (5)
C12	0.08634 (11)	0.2523 (4)	0.15939 (10)	0.0188 (5)
H12	0.0928	0.1274	0.1352	0.023*
C13	0.10753 (12)	0.2303 (4)	0.21606 (10)	0.0202 (5)
H13	0.1286	0.0915	0.2310	0.024*
C14	0.03310 (11)	0.4762 (4)	0.07712 (10)	0.0177 (5)
O3	0.00181 (9)	0.6673 (3)	0.06089 (7)	0.0272 (4)
H3O	−0.0102	0.6630	0.0263	0.041*
O4	0.04427 (9)	0.3198 (3)	0.04501 (7)	0.0244 (4)
O5	0.17781 (9)	0.2955 (3)	0.56890 (7)	0.0238 (4)
C15	0.21608 (12)	0.4869 (4)	0.59482 (10)	0.0202 (5)
H15A	0.1923	0.6365	0.5875	0.024*
H15B	0.2568	0.4988	0.5799	0.024*
C16	0.22997 (12)	0.4371 (4)	0.65666 (10)	0.0207 (5)
H16A	0.2560	0.2922	0.6636	0.025*
H16B	0.1889	0.4117	0.6704	0.025*
C17	0.26641 (13)	0.6408 (5)	0.68816 (11)	0.0277 (6)
H17A	0.3098	0.6505	0.6788	0.042*
H17B	0.2696	0.6153	0.7282	0.042*
H17C	0.2433	0.7875	0.6777	0.042*

	U11	U22	U33	U12	U13	U23
C1	0.0169 (12)	0.0177 (11)	0.0174 (12)	0.0001 (9)	0.0053 (9)	−0.0012 (9)
C2	0.0269 (13)	0.0199 (12)	0.0207 (13)	−0.0054 (10)	0.0062 (10)	0.0038 (10)
C3	0.0262 (13)	0.0212 (12)	0.0214 (13)	−0.0056 (10)	0.0042 (10)	0.0002 (10)
C4	0.0189 (12)	0.0255 (13)	0.0156 (12)	0.0005 (10)	0.0044 (10)	0.0003 (10)
C5	0.0275 (14)	0.0237 (12)	0.0184 (13)	−0.0057 (10)	0.0061 (10)	0.0025 (10)
C6	0.0220 (13)	0.0210 (12)	0.0213 (13)	−0.0045 (10)	0.0051 (10)	−0.0004 (10)
C7	0.0181 (12)	0.0163 (11)	0.0192 (12)	0.0005 (9)	0.0058 (10)	0.0002 (9)
O1	0.0298 (10)	0.0258 (9)	0.0203 (9)	−0.0100 (8)	0.0067 (8)	−0.0043 (7)
O2	0.0274 (10)	0.0236 (9)	0.0134 (8)	−0.0069 (7)	0.0024 (7)	0.0006 (7)
C8	0.0174 (12)	0.0232 (12)	0.0138 (12)	−0.0057 (9)	0.0031 (9)	0.0022 (9)
C9	0.0193 (12)	0.0188 (11)	0.0203 (12)	−0.0009 (9)	0.0063 (10)	−0.0032 (9)
C10	0.0175 (12)	0.0176 (11)	0.0184 (12)	0.0006 (9)	0.0045 (9)	0.0013 (9)
C11	0.0136 (11)	0.0193 (11)	0.0181 (12)	−0.0008 (9)	0.0040 (9)	0.0014 (9)
C12	0.0204 (12)	0.0173 (11)	0.0198 (12)	−0.0009 (9)	0.0072 (10)	−0.0012 (9)
C13	0.0208 (12)	0.0199 (12)	0.0200 (12)	−0.0007 (9)	0.0036 (10)	0.0021 (9)
C14	0.0153 (11)	0.0190 (11)	0.0196 (12)	0.0013 (9)	0.0055 (9)	−0.0009 (9)
O3	0.0382 (11)	0.0267 (10)	0.0155 (9)	0.0145 (8)	0.0012 (8)	0.0001 (7)
O4	0.0296 (10)	0.0244 (9)	0.0193 (9)	0.0073 (8)	0.0043 (7)	−0.0031 (7)
O5	0.0281 (10)	0.0259 (9)	0.0168 (9)	−0.0071 (8)	0.0024 (7)	0.0004 (7)
C15	0.0200 (12)	0.0220 (12)	0.0184 (12)	−0.0036 (10)	0.0029 (10)	−0.0007 (10)
C16	0.0181 (12)	0.0269 (13)	0.0174 (12)	0.0002 (10)	0.0035 (10)	0.0009 (10)
C17	0.0284 (14)	0.0338 (15)	0.0200 (13)	−0.0014 (11)	0.0012 (11)	0.0000 (11)

C1—C2	1.385 (3)	C10—H10	0.9500
C1—C6	1.400 (3)	C11—C12	1.394 (3)
C1—C7	1.480 (3)	C11—C14	1.482 (3)
C2—C3	1.391 (4)	C12—C13	1.387 (3)
C2—H2	0.9500	C12—H12	0.9500
C3—C4	1.395 (3)	C13—H13	0.9500
C3—H3	0.9500	C14—O4	1.237 (3)
C4—O5	1.358 (3)	C14—O3	1.300 (3)
C4—C5	1.395 (3)	O3—H3O	0.8400
C5—C6	1.379 (3)	O5—C15	1.438 (3)
C5—H5	0.9500	C15—C16	1.516 (3)
C6—H6	0.9500	C15—H15A	0.9900
C7—O1	1.204 (3)	C15—H15B	0.9900
C7—O2	1.367 (3)	C16—C17	1.527 (4)
O2—C8	1.406 (3)	C16—H16A	0.9900
C8—C9	1.380 (3)	C16—H16B	0.9900
C8—C13	1.385 (3)	C17—H17A	0.9800
C9—C10	1.389 (3)	C17—H17B	0.9800
C9—H9	0.9500	C17—H17C	0.9800
C10—C11	1.389 (3)
C2—C1—C6	119.3 (2)	C10—C11—C14	120.7 (2)
C2—C1—C7	123.2 (2)	C12—C11—C14	119.3 (2)
C6—C1—C7	117.6 (2)	C13—C12—C11	120.2 (2)
C1—C2—C3	120.8 (2)	C13—C12—H12	119.9
C1—C2—H2	119.6	C11—C12—H12	119.9
C3—C2—H2	119.6	C8—C13—C12	118.6 (2)
C2—C3—C4	119.6 (2)	C8—C13—H13	120.7
C2—C3—H3	120.2	C12—C13—H13	120.7
C4—C3—H3	120.2	O4—C14—O3	123.5 (2)
O5—C4—C3	124.9 (2)	O4—C14—C11	121.2 (2)
O5—C4—C5	115.3 (2)	O3—C14—C11	115.3 (2)
C3—C4—C5	119.7 (2)	C14—O3—H3O	109.5
C6—C5—C4	120.2 (2)	C4—O5—C15	118.32 (19)
C6—C5—H5	119.9	O5—C15—C16	107.18 (19)
C4—C5—H5	119.9	O5—C15—H15A	110.3
C5—C6—C1	120.4 (2)	C16—C15—H15A	110.3
C5—C6—H6	119.8	O5—C15—H15B	110.3
C1—C6—H6	119.8	C16—C15—H15B	110.3
O1—C7—O2	122.9 (2)	H15A—C15—H15B	108.5
O1—C7—C1	125.5 (2)	C15—C16—C17	110.8 (2)
O2—C7—C1	111.61 (19)	C15—C16—H16A	109.5
C7—O2—C8	118.23 (18)	C17—C16—H16A	109.5
C9—C8—C13	122.2 (2)	C15—C16—H16B	109.5
C9—C8—O2	116.1 (2)	C17—C16—H16B	109.5
C13—C8—O2	121.7 (2)	H16A—C16—H16B	108.1
C8—C9—C10	118.8 (2)	C16—C17—H17A	109.5
C8—C9—H9	120.6	C16—C17—H17B	109.5
C10—C9—H9	120.6	H17A—C17—H17B	109.5
C11—C10—C9	120.2 (2)	C16—C17—H17C	109.5
C11—C10—H10	119.9	H17A—C17—H17C	109.5
C9—C10—H10	119.9	H17B—C17—H17C	109.5
C10—C11—C12	120.0 (2)
C6—C1—C2—C3	0.2 (4)	C13—C8—C9—C10	1.5 (4)
C7—C1—C2—C3	179.7 (2)	O2—C8—C9—C10	178.5 (2)
C1—C2—C3—C4	0.0 (4)	C8—C9—C10—C11	−1.1 (3)
C2—C3—C4—O5	−179.5 (2)	C9—C10—C11—C12	0.2 (3)
C2—C3—C4—C5	−0.3 (4)	C9—C10—C11—C14	−179.8 (2)
O5—C4—C5—C6	179.7 (2)	C10—C11—C12—C13	0.3 (3)
C3—C4—C5—C6	0.3 (4)	C14—C11—C12—C13	−179.7 (2)
C4—C5—C6—C1	−0.1 (4)	C9—C8—C13—C12	−1.1 (4)
C2—C1—C6—C5	−0.1 (4)	O2—C8—C13—C12	−177.8 (2)
C7—C1—C6—C5	−179.7 (2)	C11—C12—C13—C8	0.2 (4)
C2—C1—C7—O1	−176.3 (2)	C10—C11—C14—O4	175.9 (2)
C6—C1—C7—O1	3.3 (4)	C12—C11—C14—O4	−4.1 (3)
C2—C1—C7—O2	3.8 (3)	C10—C11—C14—O3	−3.7 (3)
C6—C1—C7—O2	−176.6 (2)	C12—C11—C14—O3	176.3 (2)
O1—C7—O2—C8	4.9 (3)	C3—C4—O5—C15	−0.4 (4)
C1—C7—O2—C8	−175.2 (2)	C5—C4—O5—C15	−179.7 (2)
C7—O2—C8—C9	122.6 (2)	C4—O5—C15—C16	−177.7 (2)
C7—O2—C8—C13	−60.5 (3)	O5—C15—C16—C17	−175.9 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3O···O4i	0.84	1.77	2.606 (3)	172.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3O⋯O4i	0.84	1.77	2.606 (3)	172

Symmetry code: (i) .