4-(4-Octyloxybenzo­yloxy)benzoic acid

Muhammad, K.; Khawar Rauf, M.; Ebihara, M.; Hameed, S.

doi:10.1107/S1600536809003298

organic compounds

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ISSN: 2056-9890

Volume 65| Part 2| February 2009| Page o424

doi:10.1107/S1600536809003298

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4-(4-Octyloxybenzoyloxy)benzoic acid

Khushi Muhammad,^a M. Khawar Rauf,^a Masahiro Ebihara ^b and Shahid Hameed ^a ^*

^aDepartment of Chemistry, Quaid-i-Azam University, Islamabad 45320, Pakistan, and ^bDepartment of Chemistry, Faculty of Engineering, Gifu University, Yanagido, Gifu 501-1193, Japan
^*Correspondence e-mail: shameed@qau.edu.pk

(Received 22 January 2009; accepted 27 January 2009; online 31 January 2009)

The title compound, C₂₂H₂₆O₅, is an important intermediate for the synthesis of side-chain ligands for polymeric liquid crystals. The octyl group is coplanar with the central C₆O moiety, where the maximum deviation of a C atom in the octyl group from the C₆O plane is 0.161 (5) Å. The crystal structure is stabilized by intermolecular 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_r = 370.43
Monoclinic, P 2₁ /n
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[F² > 2σ(F²)] = 0.081
wR(F²) = 0.138
S = 1.31
4358 reflections
247 parameters
H-atom parameters constrained
Δρ_max = 0.28 e Å⁻³
Δρ_min = −0.19 e Å⁻³

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) -x+2, -y+1, -z+1.

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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809003298/hg2473sup1.cif

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

checkCIF report

Comment top

Aromatic carboxylic acids bearing different substituents have been investigated for their liquid crystalline properties (Naoum et al., 2008; Nazir et al., 2008a,b). Such acids have been utilized in the synthesis of both side-chain (Gabert et al., 2006) and main-chain (Aranzazu et al., 2006) liquid crystal polymers. In addition to their use as intermediates in the synthesis of a large number of organic compounds (Hussain et al., 2005; Shafiq et al., 2005; Ahmad et al., 2003), carboxylic acids has also been used in the pharmaceutical industry (Ribeiro et al., 2008; Hameed & Rama 2004). The title compound (I) was synthesized as an intermediate in the synthesis of side-chain liquid crystal polymers. In the present report, the crystal structure of (I) is being presented. Bond lengths and angles are within the normal ranges as given for benzoyloxybenzoic acids (Muhammad et al., 2008; Hartung et al., 1997). The C7—O1 and C7—O2 bond lengths are 1.205 (3) and 1.369 (3) Å, respectively, that reflect their double and single bond character. The very similar bond lengths of C14—O4 and C14—O3, 1.287 (3) and 1.261 (3) Å, are due to disorder of CO₂H moiety. The octyl group is coplanar with the central C₆O moiety where the max dviation of C atom in octyl group from the C₆O moiety is 0.161 (5) Å. Two molecules related by an inversion center form a dimer via two hydrogen bonds composed of two carboxyl groups as shown in Fig. 2.

Related literature top

For studies of aromatic carboxylic acids wand 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 top

To a solution of 4-hydroxybenzaldehyde (0.032 moles) in 50 ml of triethylamine (TEA), was added an equivalent amount of 4-octyloxybenzoylchloride with stirring and the mixture heated at 60°C for 1 h. The excess TEA was removed in vacuo and the product, after recrystallization from hot ethanol, was subjected to KMnO₄ oxidation.The 4-(4-octyloxybenzoyloxy)benzaldehyde (0.025 moles) was dissolved in acetone (100 ml) and aqueous KMnO₄ (0.025 moles) was added dropwise at room temperature with stirring. The stirring was continued for three hours when the reaction mixture was filtered and the filtrate acidified using 6M HCl. The precipitated product was purified by recrystallization from acetone.

Computing details top

Data collection: CrystalClear (Molecular Structure Corporation & Rigaku, 2001); cell refinement: CrystalClear (Molecular Structure Corporation & Rigaku, 2001); 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 (Sheldrick, 2008) and TEXSAN (Molecular Structure Corporation & Rigaku, 2004).

Figures top

	Fig. 1. Molecular structure of (I) showing atom-labelling scheme and displacement ellipsoids at the 30% probability level.
	Fig. 2. Showing hydrogen bonded molecules through O—H···O.

4-(4-Octyloxybenzoyloxy)benzoic acid top

Crystal data top

C₂₂H₂₆O₅	F(000) = 792
M_r = 370.43	D_x = 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

Data collection top

Rigaku/MSC Mercury CCD diffractometer	3870 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.048
Graphite monochromator	θ_max = 27.5°, θ_min = 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 top

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(F_o²) + (0.0263P)² + 1.5055P] where P = (F_o² + 2F_c²)/3
4358 reflections	(Δ/σ)_max < 0.001
247 parameters	Δρ_max = 0.28 e Å⁻³
0 restraints	Δρ_min = −0.19 e Å⁻³

Crystal data top

C₂₂H₂₆O₅	V = 1907.5 (18) Å³
M_r = 370.43	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 13.528 (8) Å	µ = 0.09 mm⁻¹
b = 7.245 (4) Å	T = 123 K
c = 20.903 (12) Å	0.40 × 0.30 × 0.15 mm
β = 111.407 (8)°

Data collection top

Rigaku/MSC Mercury CCD diffractometer	3870 reflections with I > 2σ(I)
14669 measured reflections	R_int = 0.048
4358 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.081	0 restraints
wR(F²) = 0.138	H-atom parameters constrained
S = 1.31	Δρ_max = 0.28 e Å⁻³
4358 reflections	Δρ_min = −0.19 e Å⁻³
247 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x+2, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₂₂H₂₆O₅
M_r	370.43
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	123
a, b, c (Å)	13.528 (8), 7.245 (4), 20.903 (12)
β (°)	111.407 (8)
V (Å³)	1907.5 (18)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.40 × 0.30 × 0.15

Data collection
Diffractometer	Rigaku/MSC Mercury CCD diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	14669, 4358, 3870
R_int	0.048
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.081, 0.138, 1.31
No. of reflections	4358
No. of parameters	247
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.28, −0.19

Computer programs: CrystalClear (Molecular Structure Corporation & Rigaku, 2001), SIR97 (Altomare et al., 1999), ORTEPII (Johnson, 1976), SHELXL97 (Sheldrick, 2008) and TEXSAN (Molecular Structure Corporation & Rigaku, 2004).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3O···O4ⁱ	0.84	1.85	2.659 (3)	161.2
O4—H4O···O3ⁱ	0.84	1.83	2.659 (3)	171.1

Symmetry code: (i) −x+2, −y+1, −z+1.

Acknowledgements

MKR is grateful to the Higher Education Commission of Pakistan for financial support under the International Support Initiative Programme for a doctoral fellowship at Gifu University, Japan.

References

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