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

The title compound, C(22)H(26)O(5), is an important inter-mediate for the synthesis of side-chain ligands for polymeric liquid crystals. The octyl group is coplanar with the central C(6)O moiety, where the maximum deviation of a C atom in the octyl group from the C(6)O plane is 0.161 (5) Å. The crystal structure is stabilized by inter-molecular O-H⋯O hydrogen bonds.

Related literature

For studies of aromatic carboxylic acids and their applications, see: Naoum et al. (2008 ▶); Nazir et al. (2008a ▶,b ▶); Gabert et al. (2006 ▶); Aranzazu et al. (2006 ▶); Hussain et al. (2005 ▶); Shafiq et al. (2005 ▶); Ahmad et al. (2003 ▶); Ribeiro et al. (2008 ▶); Hameed & Rama (2004 ▶); For related structures, see: Muhammad et al. (2008 ▶); Hartung et al. (1997 ▶)

Experimental

Crystal data

C22H26O5

M = 370.43

Monoclinic,

a = 13.528 (8) Å

b = 7.245 (4) Å

c = 20.903 (12) Å

β = 111.407 (8)°

V = 1907.5 (18) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 123 K

0.40 × 0.30 × 0.15 mm

Data collection

Rigaku/MSC Mercury CCD diffractometer

Absorption correction: none

14669 measured reflections

4358 independent reflections

3870 reflections with I > 2σ(I)

R int = 0.048

Refinement

R[F 2 > 2σ(F 2)] = 0.081

wR(F 2) = 0.138

S = 1.31

4358 reflections

247 parameters

H-atom parameters constrained

Δρmax = 0.28 e Å−3

Δρmin = −0.19 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/S1600536809003298/hg2473sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809003298/hg2473Isup2.hkl

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

C22H26O5	F(000) = 792
Mr = 370.43	Dx = 1.290 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71070 Å
Hall symbol: -P 2yn	Cell parameters from 4339 reflections
a = 13.528 (8) Å	θ = 3.0–27.5°
b = 7.245 (4) Å	µ = 0.09 mm−1
c = 20.903 (12) Å	T = 123 K
β = 111.407 (8)°	Chip, colourless
V = 1907.5 (18) Å3	0.40 × 0.30 × 0.15 mm
Z = 4

Rigaku/MSC Mercury CCD diffractometer	3870 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.048
graphite	θmax = 27.5°, θmin = 3.2°
Detector resolution: 14.62 pixels mm-1	h = −17→15
ω scans	k = −7→9
14669 measured reflections	l = −25→27
4358 independent reflections

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)] = 0.081	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.138	H-atom parameters constrained
S = 1.31	w = 1/[σ2(Fo2) + (0.0263P)2 + 1.5055P] where P = (Fo2 + 2Fc2)/3
4358 reflections	(Δ/σ)max < 0.001
247 parameters	Δρmax = 0.28 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	Occ. (<1)
C1	0.22298 (16)	0.5733 (3)	0.30577 (10)	0.0181 (4)
C2	0.19154 (16)	0.5148 (3)	0.23723 (10)	0.0218 (5)
H2	0.2435	0.4795	0.2189	0.026*
C3	0.08502 (17)	0.5086 (3)	0.19644 (11)	0.0239 (5)
H3	0.0638	0.4695	0.1500	0.029*
C4	0.00858 (16)	0.5596 (3)	0.22337 (10)	0.0202 (5)
C5	0.03873 (16)	0.6186 (3)	0.29139 (10)	0.0204 (5)
H5	−0.0132	0.6530	0.3099	0.024*
C6	0.14626 (17)	0.6261 (3)	0.33158 (10)	0.0211 (5)
H6	0.1676	0.6683	0.3777	0.025*
C7	0.33624 (16)	0.5860 (3)	0.35119 (10)	0.0189 (4)
O1	0.36934 (12)	0.6558 (2)	0.40736 (7)	0.0245 (4)
O2	0.40082 (11)	0.5073 (2)	0.32137 (7)	0.0231 (4)
C8	0.51107 (16)	0.5074 (3)	0.35729 (10)	0.0198 (5)
C9	0.55644 (17)	0.4315 (3)	0.42229 (11)	0.0218 (5)
H9	0.5133	0.3826	0.4453	0.026*
C10	0.66633 (16)	0.4284 (3)	0.45304 (11)	0.0201 (4)
H10	0.6987	0.3783	0.4979	0.024*
C11	0.72990 (16)	0.4980 (3)	0.41892 (10)	0.0174 (4)
C12	0.68191 (16)	0.5711 (3)	0.35287 (10)	0.0191 (4)
H12	0.7246	0.6174	0.3291	0.023*
C13	0.57211 (17)	0.5762 (3)	0.32203 (10)	0.0210 (5)
H13	0.5392	0.6262	0.2772	0.025*
C14	0.84738 (16)	0.4969 (3)	0.45311 (10)	0.0182 (4)
O3	0.88859 (12)	0.4343 (2)	0.51339 (7)	0.0257 (4)
H3O	0.9550	0.4364	0.5257	0.038*	0.50
O4	0.90241 (12)	0.5614 (2)	0.41929 (8)	0.0258 (4)
H4O	0.9671	0.5599	0.4443	0.039*	0.50
O5	−0.09388 (11)	0.5459 (2)	0.17868 (7)	0.0249 (4)
C15	−0.17837 (16)	0.5852 (3)	0.20264 (10)	0.0205 (5)
H15A	−0.1738	0.7146	0.2188	0.025*
H15B	−0.1743	0.5023	0.2412	0.025*
C16	−0.28096 (16)	0.5541 (3)	0.14232 (10)	0.0196 (4)
H16A	−0.2839	0.4239	0.1273	0.024*
H16B	−0.2814	0.6332	0.1036	0.024*
C17	−0.37919 (16)	0.5958 (3)	0.15880 (10)	0.0214 (5)
H17A	−0.3764	0.7258	0.1740	0.026*
H17B	−0.3792	0.5161	0.1973	0.026*
C18	−0.48182 (16)	0.5646 (3)	0.09742 (10)	0.0212 (5)
H18A	−0.4790	0.6383	0.0582	0.025*
H18B	−0.4857	0.4329	0.0841	0.025*
C19	−0.58294 (16)	0.6147 (3)	0.10966 (10)	0.0219 (5)
H19A	−0.5865	0.5417	0.1488	0.026*
H19B	−0.5806	0.7470	0.1221	0.026*
C20	−0.68233 (16)	0.5782 (3)	0.04655 (10)	0.0205 (5)
H20A	−0.6752	0.6432	0.0068	0.025*
H20B	−0.6864	0.4443	0.0364	0.025*
C21	−0.78576 (17)	0.6380 (4)	0.05333 (11)	0.0264 (5)
H21A	−0.7825	0.7718	0.0635	0.032*
H21B	−0.7944	0.5718	0.0924	0.032*
C22	−0.88171 (17)	0.5991 (3)	−0.01178 (12)	0.0261 (5)
H22A	−0.8708	0.6557	−0.0513	0.039*
H22B	−0.9456	0.6510	−0.0070	0.039*
H22C	−0.8904	0.4654	−0.0189	0.039*

	U11	U22	U33	U12	U13	U23
C1	0.0150 (10)	0.0197 (11)	0.0193 (9)	−0.0018 (8)	0.0060 (8)	−0.0005 (8)
C2	0.0153 (10)	0.0294 (13)	0.0218 (10)	0.0000 (9)	0.0080 (8)	−0.0036 (9)
C3	0.0195 (11)	0.0332 (13)	0.0178 (10)	−0.0005 (10)	0.0055 (8)	−0.0049 (9)
C4	0.0153 (10)	0.0229 (12)	0.0202 (10)	−0.0004 (9)	0.0039 (8)	−0.0010 (9)
C5	0.0156 (10)	0.0266 (12)	0.0201 (10)	0.0003 (9)	0.0078 (8)	0.0002 (8)
C6	0.0190 (11)	0.0273 (12)	0.0170 (10)	0.0002 (9)	0.0066 (8)	−0.0008 (8)
C7	0.0176 (10)	0.0195 (11)	0.0204 (10)	−0.0012 (9)	0.0080 (8)	0.0012 (8)
O1	0.0180 (8)	0.0345 (10)	0.0195 (7)	−0.0007 (7)	0.0049 (6)	−0.0042 (7)
O2	0.0122 (7)	0.0339 (10)	0.0212 (7)	0.0011 (7)	0.0037 (6)	−0.0064 (7)
C8	0.0124 (10)	0.0240 (12)	0.0208 (10)	0.0011 (9)	0.0035 (8)	−0.0050 (9)
C9	0.0169 (10)	0.0244 (12)	0.0255 (10)	−0.0020 (9)	0.0095 (8)	−0.0002 (9)
C10	0.0174 (10)	0.0210 (11)	0.0210 (10)	0.0011 (9)	0.0059 (8)	0.0006 (9)
C11	0.0153 (10)	0.0159 (11)	0.0206 (9)	0.0005 (8)	0.0060 (8)	−0.0026 (8)
C12	0.0184 (10)	0.0219 (11)	0.0179 (9)	0.0005 (9)	0.0077 (8)	−0.0030 (8)
C13	0.0191 (10)	0.0266 (12)	0.0151 (9)	0.0021 (9)	0.0036 (8)	−0.0026 (8)
C14	0.0180 (10)	0.0172 (10)	0.0200 (9)	0.0004 (9)	0.0075 (8)	−0.0022 (8)
O3	0.0160 (7)	0.0338 (10)	0.0232 (8)	0.0005 (7)	0.0024 (6)	0.0036 (7)
O4	0.0140 (7)	0.0347 (10)	0.0291 (8)	−0.0015 (7)	0.0084 (6)	0.0029 (7)
O5	0.0130 (7)	0.0395 (10)	0.0206 (7)	0.0009 (7)	0.0042 (6)	−0.0046 (7)
C15	0.0158 (10)	0.0259 (12)	0.0203 (10)	0.0000 (9)	0.0071 (8)	0.0012 (9)
C16	0.0154 (10)	0.0211 (11)	0.0205 (10)	0.0005 (9)	0.0045 (8)	−0.0001 (8)
C17	0.0162 (10)	0.0266 (12)	0.0194 (10)	0.0008 (9)	0.0042 (8)	−0.0015 (9)
C18	0.0170 (10)	0.0253 (12)	0.0189 (10)	−0.0003 (9)	0.0038 (8)	−0.0007 (9)
C19	0.0173 (10)	0.0267 (13)	0.0201 (10)	−0.0004 (9)	0.0050 (8)	−0.0019 (9)
C20	0.0158 (10)	0.0248 (12)	0.0198 (10)	−0.0002 (9)	0.0050 (8)	0.0003 (9)
C21	0.0191 (11)	0.0376 (14)	0.0231 (11)	0.0044 (10)	0.0084 (9)	0.0004 (10)
C22	0.0152 (10)	0.0282 (13)	0.0333 (12)	0.0005 (9)	0.0068 (9)	−0.0001 (10)

C1—C6	1.387 (3)	O3—H3O	0.8400
C1—C2	1.403 (3)	O4—H4O	0.8400
C1—C7	1.482 (3)	O5—C15	1.434 (3)
C2—C3	1.382 (3)	C15—C16	1.513 (3)
C2—H2	0.9500	C15—H15A	0.9900
C3—C4	1.396 (3)	C15—H15B	0.9900
C3—H3	0.9500	C16—C17	1.520 (3)
C4—O5	1.363 (2)	C16—H16A	0.9900
C4—C5	1.396 (3)	C16—H16B	0.9900
C5—C6	1.390 (3)	C17—C18	1.525 (3)
C5—H5	0.9500	C17—H17A	0.9900
C6—H6	0.9500	C17—H17B	0.9900
C7—O1	1.205 (3)	C18—C19	1.525 (3)
C7—O2	1.369 (3)	C18—H18A	0.9900
O2—C8	1.404 (2)	C18—H18B	0.9900
C8—C9	1.384 (3)	C19—C20	1.524 (3)
C8—C13	1.385 (3)	C19—H19A	0.9900
C9—C10	1.388 (3)	C19—H19B	0.9900
C9—H9	0.9500	C20—C21	1.520 (3)
C10—C11	1.397 (3)	C20—H20A	0.9900
C10—H10	0.9500	C20—H20B	0.9900
C11—C12	1.398 (3)	C21—C22	1.526 (3)
C11—C14	1.486 (3)	C21—H21A	0.9900
C12—C13	1.387 (3)	C21—H21B	0.9900
C12—H12	0.9500	C22—H22A	0.9800
C13—H13	0.9500	C22—H22B	0.9800
C14—O3	1.261 (3)	C22—H22C	0.9800
C14—O4	1.287 (3)
C6—C1—C2	119.32 (19)	O5—C15—H15A	110.4
C6—C1—C7	118.64 (19)	C16—C15—H15A	110.4
C2—C1—C7	122.02 (19)	O5—C15—H15B	110.4
C3—C2—C1	119.9 (2)	C16—C15—H15B	110.4
C3—C2—H2	120.0	H15A—C15—H15B	108.6
C1—C2—H2	120.0	C15—C16—C17	113.15 (18)
C2—C3—C4	120.1 (2)	C15—C16—H16A	108.9
C2—C3—H3	119.9	C17—C16—H16A	108.9
C4—C3—H3	119.9	C15—C16—H16B	108.9
O5—C4—C5	124.50 (19)	C17—C16—H16B	108.9
O5—C4—C3	114.96 (19)	H16A—C16—H16B	107.8
C5—C4—C3	120.54 (19)	C16—C17—C18	112.50 (18)
C6—C5—C4	118.7 (2)	C16—C17—H17A	109.1
C6—C5—H5	120.7	C18—C17—H17A	109.1
C4—C5—H5	120.7	C16—C17—H17B	109.1
C1—C6—C5	121.39 (19)	C18—C17—H17B	109.1
C1—C6—H6	119.3	H17A—C17—H17B	107.8
C5—C6—H6	119.3	C19—C18—C17	114.88 (18)
O1—C7—O2	123.14 (19)	C19—C18—H18A	108.5
O1—C7—C1	125.5 (2)	C17—C18—H18A	108.5
O2—C7—C1	111.40 (17)	C19—C18—H18B	108.5
C7—O2—C8	119.08 (16)	C17—C18—H18B	108.5
C9—C8—C13	121.90 (19)	H18A—C18—H18B	107.5
C9—C8—O2	121.9 (2)	C20—C19—C18	112.06 (18)
C13—C8—O2	116.03 (18)	C20—C19—H19A	109.2
C8—C9—C10	118.5 (2)	C18—C19—H19A	109.2
C8—C9—H9	120.8	C20—C19—H19B	109.2
C10—C9—H9	120.8	C18—C19—H19B	109.2
C9—C10—C11	120.9 (2)	H19A—C19—H19B	107.9
C9—C10—H10	119.6	C21—C20—C19	114.91 (18)
C11—C10—H10	119.6	C21—C20—H20A	108.5
C10—C11—C12	119.38 (19)	C19—C20—H20A	108.5
C10—C11—C14	120.15 (19)	C21—C20—H20B	108.5
C12—C11—C14	120.46 (19)	C19—C20—H20B	108.5
C13—C12—C11	120.1 (2)	H20A—C20—H20B	107.5
C13—C12—H12	119.9	C20—C21—C22	112.13 (19)
C11—C12—H12	119.9	C20—C21—H21A	109.2
C8—C13—C12	119.24 (19)	C22—C21—H21A	109.2
C8—C13—H13	120.4	C20—C21—H21B	109.2
C12—C13—H13	120.4	C22—C21—H21B	109.2
O3—C14—O4	123.08 (19)	H21A—C21—H21B	107.9
O3—C14—C11	119.19 (19)	C21—C22—H22A	109.5
O4—C14—C11	117.73 (18)	C21—C22—H22B	109.5
C14—O3—H3O	109.5	H22A—C22—H22B	109.5
C14—O4—H4O	109.5	C21—C22—H22C	109.5
C4—O5—C15	119.13 (17)	H22A—C22—H22C	109.5
O5—C15—C16	106.55 (17)	H22B—C22—H22C	109.5
C6—C1—C2—C3	−0.6 (3)	C9—C10—C11—C12	−0.2 (3)
C7—C1—C2—C3	−178.8 (2)	C9—C10—C11—C14	178.9 (2)
C1—C2—C3—C4	−0.3 (4)	C10—C11—C12—C13	0.8 (3)
C2—C3—C4—O5	−179.2 (2)	C14—C11—C12—C13	−178.3 (2)
C2—C3—C4—C5	0.5 (4)	C9—C8—C13—C12	−0.8 (3)
O5—C4—C5—C6	179.9 (2)	O2—C8—C13—C12	−176.44 (19)
C3—C4—C5—C6	0.2 (3)	C11—C12—C13—C8	−0.3 (3)
C2—C1—C6—C5	1.4 (3)	C10—C11—C14—O3	−0.8 (3)
C7—C1—C6—C5	179.6 (2)	C12—C11—C14—O3	178.3 (2)
C4—C5—C6—C1	−1.2 (3)	C10—C11—C14—O4	179.5 (2)
C6—C1—C7—O1	−7.8 (4)	C12—C11—C14—O4	−1.4 (3)
C2—C1—C7—O1	170.4 (2)	C5—C4—O5—C15	−3.2 (3)
C6—C1—C7—O2	172.24 (19)	C3—C4—O5—C15	176.5 (2)
C2—C1—C7—O2	−9.6 (3)	C4—O5—C15—C16	−178.78 (19)
O1—C7—O2—C8	−0.1 (3)	O5—C15—C16—C17	−178.28 (18)
C1—C7—O2—C8	179.84 (18)	C15—C16—C17—C18	179.72 (19)
C7—O2—C8—C9	56.4 (3)	C16—C17—C18—C19	−176.7 (2)
C7—O2—C8—C13	−128.0 (2)	C17—C18—C19—C20	−179.4 (2)
C13—C8—C9—C10	1.4 (3)	C18—C19—C20—C21	−175.8 (2)
O2—C8—C9—C10	176.7 (2)	C19—C20—C21—C22	179.5 (2)
C8—C9—C10—C11	−0.8 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3O···O4i	0.84	1.85	2.659 (3)	161
O4—H4O···O3i	0.84	1.83	2.659 (3)	171

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3O⋯O4i	0.84	1.85	2.659 (3)	161
O4—H4O⋯O3i	0.84	1.83	2.659 (3)	171

Symmetry code: (i) .