tert-Butyl 2-[4-(2-{4-[(tert-butoxycar­bonyl)methoxy]-3-methylphenyl}-2-propyl)-2-methylphenoxy]acetate

Ali, Q.; Yousuf, S.; Raza Shah, M.; Ng, S.W.

doi:10.1107/S1600536810023433

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 66| Part 7| July 2010| Page o1750

doi:10.1107/S1600536810023433

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tert-Butyl 2-[4-(2-{4-[(tert-butoxycarbonyl)methoxy]-3-methylphenyl}-2-propyl)-2-methylphenoxy]acetate

Qamar Ali,^a Sammer Yousuf,^a Muhammad Raza Shah ^a and Seik Weng Ng ^b ^*

^aHEJ Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, Karachi 75270, Pakistan, and ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 14 June 2010; accepted 17 June 2010; online 23 June 2010)

In the molecule of the title compound, C₂₉H₄₀O₆, the carbon atom belonging to the propyl chain is connected to two aromatic rings that open up the C_aryl—C—C_aryl angle to 111.5 (1)°. The four-atom –O–CH₂–C(=O)–O– linkage between the aromatic ring and the tert-butyl group assumes a (−)anti-periplanar conformation for one substituent and a (−)syn-periplanar conformation for the other substituent; the O–C–C–O torsion angles are −173.7 (2) and −10.2 (3)°.

Related literature

For the crystal structure of a related V-shaped molecule, see: Shah et al. (2010 ).

Experimental

Crystal data

C₂₉H₄₀O₆
M_r = 484.61
Triclinic, $[P \overline 1]$
a = 8.3154 (6) Å
b = 12.5589 (8) Å
c = 13.9410 (9) Å
α = 101.782 (1)°
β = 97.529 (1)°
γ = 94.156 (1)°
V = 1405.52 (16) Å³
Z = 2
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 293 K
0.45 × 0.35 × 0.30 mm

Data collection

Bruker SMART APEX diffractometer
13784 measured reflections
6428 independent reflections
4482 reflections with I > 2σ(I)
R_int = 0.021

Refinement

R[F² > 2σ(F²)] = 0.060
wR(F²) = 0.184
S = 1.03
6428 reflections
318 parameters
H-atom parameters constrained
Δρ_max = 0.35 e Å⁻³
Δρ_min = −0.19 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: X-SEED (Barbour, 2001 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810023433/ci5103sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810023433/ci5103Isup2.hkl

checkCIF report

Comment top

We are interested in the solid-state structures of V-shaped molecules. A recent study reported the crystal structure of 9,9-bis[4-(tert-butoxycarbonylmethyloxy)phenyl]fluorene, a compound used as dissolution inhibitor for protecting photosensitive poly(benzoxazole)s (Shah et al., 2010). The V shape induced by the fluorenyl portion is now replaced by an i-propyl unit to furnish a similarly shaped molecule (Scheme I, Fig. 1). In the title molecule, the carbon atom belonging to the propyl chain is connected to two aromatic rings that open up the C_aryl–C–C_aryl to 111.5 (1)°. The four-atom –O–CH₂–C(═O)–O– chain between the aromatic ring and the tert-butyl group assumes a W shape for one substituent and a U shape for the other substituent [O–C–C–O torsion angle -173.7 (2)° and -10.2 (3)°].

Related literature top

For the crystal structure of a related V-shaped molecule, see: Shah et al. (2010).

Experimental top

2,2-Bis(4-hydroxy-3-methylphenyl)propane (0.50 g) and potassium carbonate (0.85 g) were placed in acetone (25 ml) and to this was added tert-butyl bromoacetate (0.75 ml, 5 mmol). The mixture was stirred at room temperature for 3 h. The solvent was evaporated under reduced pressure and the residue was dissolved in a mixture of water (50 ml) and dichloromethane (50 ml). The aqueous layer was extracted three times with dichloromethane. The combined organic phases were evaporated under reduced pressure and the solid material was recrystallized from n-hexane. Colourless crystals were obtained in 80% yield.

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

Fig. 1. Displacement ellipsoid plot (Barbour, 2001) of C₂₉H₄₀O₆ at the 50% probability level. H atoms are drawn as spheres of arbitrary radius.

tert-Butyl 2-[4-(2-{4-[(tert-butoxycarbonyl)methoxy]- 3-methylphenyl}-2-propyl)-2-methylphenoxy]acetate top

Crystal data top

C₂₉H₄₀O₆	Z = 2
M_r = 484.61	F(000) = 524
Triclinic, P1	D_x = 1.145 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.3154 (6) Å	Cell parameters from 4014 reflections
b = 12.5589 (8) Å	θ = 2.5–27.3°
c = 13.9410 (9) Å	µ = 0.08 mm⁻¹
α = 101.782 (1)°	T = 293 K
β = 97.529 (1)°	Block, colourless
γ = 94.156 (1)°	0.45 × 0.35 × 0.30 mm
V = 1405.52 (16) Å³

Data collection top

Bruker SMART APEX diffractometer	4482 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.021
Graphite monochromator	θ_max = 27.5°, θ_min = 1.7°
ω scans	h = −10→10
13784 measured reflections	k = −16→14
6428 independent reflections	l = −18→17

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)] = 0.060	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.184	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0989P)² + 0.2549P] where P = (F_o² + 2F_c²)/3
6428 reflections	(Δ/σ)_max = 0.001
318 parameters	Δρ_max = 0.35 e Å⁻³
0 restraints	Δρ_min = −0.19 e Å⁻³

Crystal data top

C₂₉H₄₀O₆	γ = 94.156 (1)°
M_r = 484.61	V = 1405.52 (16) Å³
Triclinic, P1	Z = 2
a = 8.3154 (6) Å	Mo Kα radiation
b = 12.5589 (8) Å	µ = 0.08 mm⁻¹
c = 13.9410 (9) Å	T = 293 K
α = 101.782 (1)°	0.45 × 0.35 × 0.30 mm
β = 97.529 (1)°

Data collection top

Bruker SMART APEX diffractometer	4482 reflections with I > 2σ(I)
13784 measured reflections	R_int = 0.021
6428 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.060	0 restraints
wR(F²) = 0.184	H-atom parameters constrained
S = 1.03	Δρ_max = 0.35 e Å⁻³
6428 reflections	Δρ_min = −0.19 e Å⁻³
318 parameters

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

	x	y	z	U_iso*/U_eq
O1	0.54867 (16)	0.16145 (12)	0.44990 (9)	0.0584 (4)
O2	0.28231 (18)	0.17998 (13)	0.40617 (11)	0.0644 (4)
O3	0.22035 (16)	0.13010 (10)	0.58548 (10)	0.0537 (3)
O4	0.13940 (17)	0.83903 (11)	1.01874 (10)	0.0608 (4)
O5	0.4354 (2)	0.79162 (18)	1.21064 (11)	0.0891 (6)
O6	0.43525 (16)	0.77133 (14)	1.04833 (10)	0.0665 (4)
C1	0.6069 (3)	0.17993 (18)	0.35761 (14)	0.0571 (5)
C2	0.7872 (3)	0.1715 (3)	0.3802 (2)	0.1093 (12)
H2A	0.8337	0.2275	0.4369	0.164*
H2B	0.8384	0.1808	0.3242	0.164*
H2C	0.8044	0.1010	0.3939	0.164*
C3	0.5730 (4)	0.29242 (19)	0.34262 (19)	0.0811 (7)
H3A	0.6249	0.3465	0.3994	0.122*
H3B	0.4575	0.2972	0.3344	0.122*
H3C	0.6150	0.3051	0.2846	0.122*
C4	0.5265 (4)	0.0919 (2)	0.27129 (18)	0.0882 (8)
H4A	0.4108	0.0961	0.2625	0.132*
H4B	0.5486	0.0216	0.2839	0.132*
H4C	0.5685	0.1016	0.2124	0.132*
C5	0.3936 (2)	0.16414 (14)	0.46314 (13)	0.0459 (4)
C6	0.3813 (2)	0.14131 (16)	0.56480 (14)	0.0516 (4)
H6A	0.4307	0.0747	0.5700	0.062*
H6B	0.4434	0.2005	0.6146	0.062*
C7	0.1432 (2)	0.22212 (13)	0.61535 (12)	0.0424 (4)
C8	0.2100 (2)	0.32846 (15)	0.62278 (14)	0.0501 (4)
H8	0.3146	0.3418	0.6082	0.060*
C9	0.1196 (2)	0.41480 (14)	0.65211 (14)	0.0506 (4)
H9	0.1661	0.4860	0.6585	0.061*
C10	−0.0379 (2)	0.39793 (13)	0.67218 (12)	0.0429 (4)
C11	−0.0997 (2)	0.29071 (14)	0.66524 (12)	0.0432 (4)
H11	−0.2045	0.2775	0.6795	0.052*
C12	−0.0121 (2)	0.20183 (13)	0.63788 (12)	0.0423 (4)
C13	−0.0854 (3)	0.08640 (15)	0.63031 (16)	0.0593 (5)
H13A	−0.1955	0.0875	0.6441	0.089*
H13B	−0.0223	0.0540	0.6774	0.089*
H13C	−0.0851	0.0443	0.5646	0.089*
C14	−0.1407 (2)	0.49513 (14)	0.69162 (14)	0.0480 (4)
C15	−0.3066 (2)	0.46110 (18)	0.7189 (2)	0.0755 (7)
H15A	−0.3641	0.4036	0.6669	0.113*
H15B	−0.3691	0.5228	0.7274	0.113*
H15C	−0.2904	0.4356	0.7796	0.113*
C16	−0.1702 (3)	0.53592 (18)	0.59406 (15)	0.0711 (7)
H16A	−0.0673	0.5558	0.5749	0.107*
H16B	−0.2309	0.5985	0.6037	0.107*
H16C	−0.2308	0.4788	0.5429	0.107*
C17	−0.0548 (2)	0.58614 (13)	0.77766 (12)	0.0403 (4)
C18	−0.0610 (2)	0.69584 (13)	0.77638 (12)	0.0402 (4)
H18	−0.1110	0.7143	0.7192	0.048*
C19	0.0042 (2)	0.77945 (13)	0.85692 (12)	0.0420 (4)
C20	0.0800 (2)	0.75110 (14)	0.94170 (13)	0.0445 (4)
C21	0.0898 (2)	0.64272 (16)	0.94550 (14)	0.0522 (4)
H21	0.1415	0.6243	1.0023	0.063*
C22	0.0220 (2)	0.56143 (15)	0.86392 (14)	0.0494 (4)
H22	0.0281	0.4886	0.8671	0.059*
C23	−0.0095 (3)	0.89746 (16)	0.85277 (17)	0.0642 (6)
H23A	0.0977	0.9358	0.8633	0.096*
H23B	−0.0696	0.9303	0.9034	0.096*
H23C	−0.0651	0.9015	0.7890	0.096*
C24	0.1975 (2)	0.8205 (2)	1.11273 (14)	0.0632 (6)
H24A	0.1263	0.7618	1.1251	0.076*
H24B	0.1881	0.8857	1.1619	0.076*
C25	0.3708 (2)	0.79182 (16)	1.12921 (13)	0.0527 (5)
C26	0.6032 (2)	0.7409 (2)	1.04549 (17)	0.0702 (6)
C27	0.6246 (5)	0.6415 (3)	1.0903 (3)	0.1357 (14)
H27A	0.6150	0.6602	1.1595	0.203*
H27B	0.7303	0.6178	1.0827	0.203*
H27C	0.5419	0.5836	1.0572	0.203*
C28	0.7205 (4)	0.8347 (3)	1.1020 (3)	0.1313 (15)
H28A	0.7017	0.8982	1.0754	0.197*
H28B	0.8299	0.8172	1.0967	0.197*
H28C	0.7055	0.8493	1.1704	0.197*
C29	0.6096 (4)	0.7084 (4)	0.9371 (2)	0.1321 (15)
H29A	0.5931	0.7701	0.9073	0.198*
H29B	0.5257	0.6502	0.9072	0.198*
H29C	0.7142	0.6842	0.9270	0.198*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0552 (8)	0.0840 (10)	0.0451 (7)	0.0226 (7)	0.0167 (6)	0.0235 (7)
O2	0.0593 (8)	0.0816 (10)	0.0560 (8)	0.0185 (7)	0.0039 (7)	0.0224 (7)
O3	0.0603 (8)	0.0434 (7)	0.0634 (8)	0.0169 (6)	0.0273 (6)	0.0100 (6)
O4	0.0636 (8)	0.0574 (8)	0.0506 (8)	0.0147 (6)	−0.0056 (6)	−0.0076 (6)
O5	0.0735 (11)	0.1484 (18)	0.0461 (9)	0.0218 (11)	0.0038 (7)	0.0219 (9)
O6	0.0487 (8)	0.1064 (12)	0.0437 (7)	0.0157 (7)	0.0103 (6)	0.0098 (7)
C1	0.0673 (12)	0.0676 (13)	0.0446 (10)	0.0186 (10)	0.0208 (9)	0.0193 (9)
C2	0.0730 (17)	0.195 (4)	0.093 (2)	0.048 (2)	0.0443 (15)	0.075 (2)
C3	0.113 (2)	0.0603 (14)	0.0764 (16)	0.0089 (13)	0.0251 (14)	0.0213 (12)
C4	0.136 (2)	0.0705 (15)	0.0585 (14)	0.0123 (15)	0.0343 (15)	0.0028 (11)
C5	0.0526 (10)	0.0408 (9)	0.0452 (9)	0.0152 (7)	0.0102 (8)	0.0055 (7)
C6	0.0563 (11)	0.0560 (11)	0.0490 (10)	0.0241 (9)	0.0171 (8)	0.0141 (8)
C7	0.0503 (9)	0.0407 (9)	0.0375 (8)	0.0122 (7)	0.0120 (7)	0.0055 (7)
C8	0.0454 (9)	0.0462 (10)	0.0595 (11)	0.0042 (8)	0.0177 (8)	0.0074 (8)
C9	0.0538 (10)	0.0344 (9)	0.0622 (11)	0.0019 (7)	0.0144 (8)	0.0049 (8)
C10	0.0462 (9)	0.0370 (8)	0.0426 (9)	0.0070 (7)	0.0067 (7)	0.0004 (7)
C11	0.0430 (9)	0.0422 (9)	0.0429 (9)	0.0042 (7)	0.0113 (7)	0.0029 (7)
C12	0.0540 (10)	0.0355 (8)	0.0372 (8)	0.0059 (7)	0.0112 (7)	0.0041 (6)
C13	0.0721 (13)	0.0401 (10)	0.0686 (13)	0.0044 (9)	0.0302 (10)	0.0066 (9)
C14	0.0489 (10)	0.0385 (9)	0.0524 (10)	0.0110 (7)	0.0031 (8)	0.0010 (7)
C15	0.0450 (11)	0.0517 (12)	0.119 (2)	0.0112 (9)	0.0138 (11)	−0.0087 (12)
C16	0.0976 (17)	0.0548 (12)	0.0504 (11)	0.0289 (11)	−0.0129 (11)	−0.0050 (9)
C17	0.0419 (8)	0.0387 (8)	0.0405 (8)	0.0093 (7)	0.0107 (7)	0.0048 (7)
C18	0.0458 (9)	0.0396 (9)	0.0369 (8)	0.0100 (7)	0.0101 (7)	0.0079 (6)
C19	0.0441 (9)	0.0388 (9)	0.0443 (9)	0.0086 (7)	0.0130 (7)	0.0061 (7)
C20	0.0413 (9)	0.0461 (9)	0.0428 (9)	0.0090 (7)	0.0075 (7)	−0.0005 (7)
C21	0.0564 (11)	0.0567 (11)	0.0432 (9)	0.0166 (8)	0.0007 (8)	0.0105 (8)
C22	0.0586 (11)	0.0391 (9)	0.0525 (10)	0.0141 (8)	0.0060 (8)	0.0129 (8)
C23	0.0833 (15)	0.0417 (10)	0.0646 (13)	0.0103 (10)	0.0068 (11)	0.0058 (9)
C24	0.0547 (11)	0.0802 (15)	0.0449 (10)	0.0143 (10)	0.0049 (8)	−0.0102 (9)
C25	0.0516 (10)	0.0627 (12)	0.0382 (9)	0.0016 (8)	0.0045 (8)	0.0010 (8)
C26	0.0450 (11)	0.0988 (18)	0.0643 (13)	0.0143 (11)	0.0131 (9)	0.0065 (12)
C27	0.140 (3)	0.116 (3)	0.163 (4)	0.069 (2)	0.040 (3)	0.029 (3)
C28	0.0605 (16)	0.132 (3)	0.174 (4)	−0.0194 (17)	0.0303 (19)	−0.027 (3)
C29	0.087 (2)	0.228 (5)	0.081 (2)	0.045 (2)	0.0380 (17)	0.007 (2)

Geometric parameters (Å, º) top

O1—C5	1.328 (2)	C13—H13C	0.96
O1—C1	1.488 (2)	C14—C15	1.533 (3)
O2—C5	1.194 (2)	C14—C17	1.534 (2)
O3—C7	1.379 (2)	C14—C16	1.545 (3)
O3—C6	1.409 (2)	C15—H15A	0.96
O4—C20	1.384 (2)	C15—H15B	0.96
O4—C24	1.407 (3)	C15—H15C	0.96
O5—C25	1.191 (2)	C16—H16A	0.96
O6—C25	1.298 (2)	C16—H16B	0.96
O6—C26	1.478 (2)	C16—H16C	0.96
C1—C4	1.502 (3)	C17—C18	1.386 (2)
C1—C2	1.507 (3)	C17—C22	1.389 (2)
C1—C3	1.511 (3)	C18—C19	1.391 (2)
C2—H2A	0.96	C18—H18	0.93
C2—H2B	0.96	C19—C20	1.389 (2)
C2—H2C	0.96	C19—C23	1.507 (3)
C3—H3A	0.96	C20—C21	1.381 (3)
C3—H3B	0.96	C21—C22	1.389 (3)
C3—H3C	0.96	C21—H21	0.93
C4—H4A	0.96	C22—H22	0.93
C4—H4B	0.96	C23—H23A	0.96
C4—H4C	0.96	C23—H23B	0.96
C5—C6	1.517 (3)	C23—H23C	0.96
C6—H6A	0.97	C24—C25	1.510 (3)
C6—H6B	0.97	C24—H24A	0.97
C7—C12	1.387 (2)	C24—H24B	0.97
C7—C8	1.387 (3)	C26—C28	1.488 (4)
C8—C9	1.388 (3)	C26—C29	1.492 (4)
C8—H8	0.93	C26—C27	1.517 (5)
C9—C10	1.385 (3)	C27—H27A	0.96
C9—H9	0.93	C27—H27B	0.96
C10—C11	1.386 (2)	C27—H27C	0.96
C10—C14	1.540 (2)	C28—H28A	0.96
C11—C12	1.392 (2)	C28—H28B	0.96
C11—H11	0.93	C28—H28C	0.96
C12—C13	1.509 (2)	C29—H29A	0.96
C13—H13A	0.96	C29—H29B	0.96
C13—H13B	0.96	C29—H29C	0.96

C5—O1—C1	122.52 (14)	C14—C15—H15B	109.5
C7—O3—C6	119.71 (14)	H15A—C15—H15B	109.5
C20—O4—C24	119.61 (16)	C14—C15—H15C	109.5
C25—O6—C26	123.23 (16)	H15A—C15—H15C	109.5
O1—C1—C4	109.56 (18)	H15B—C15—H15C	109.5
O1—C1—C2	101.98 (16)	C14—C16—H16A	109.5
C4—C1—C2	111.8 (2)	C14—C16—H16B	109.5
O1—C1—C3	109.83 (17)	H16A—C16—H16B	109.5
C4—C1—C3	111.7 (2)	C14—C16—H16C	109.5
C2—C1—C3	111.5 (2)	H16A—C16—H16C	109.5
C1—C2—H2A	109.5	H16B—C16—H16C	109.5
C1—C2—H2B	109.5	C18—C17—C22	117.09 (15)
H2A—C2—H2B	109.5	C18—C17—C14	121.98 (15)
C1—C2—H2C	109.5	C22—C17—C14	120.75 (15)
H2A—C2—H2C	109.5	C17—C18—C19	122.83 (15)
H2B—C2—H2C	109.5	C17—C18—H18	118.6
C1—C3—H3A	109.5	C19—C18—H18	118.6
C1—C3—H3B	109.5	C20—C19—C18	118.19 (15)
H3A—C3—H3B	109.5	C20—C19—C23	120.99 (16)
C1—C3—H3C	109.5	C18—C19—C23	120.81 (16)
H3A—C3—H3C	109.5	C21—C20—O4	124.86 (16)
H3B—C3—H3C	109.5	C21—C20—C19	120.66 (16)
C1—C4—H4A	109.5	O4—C20—C19	114.47 (15)
C1—C4—H4B	109.5	C20—C21—C22	119.52 (16)
H4A—C4—H4B	109.5	C20—C21—H21	120.2
C1—C4—H4C	109.5	C22—C21—H21	120.2
H4A—C4—H4C	109.5	C21—C22—C17	121.70 (16)
H4B—C4—H4C	109.5	C21—C22—H22	119.2
O2—C5—O1	127.28 (17)	C17—C22—H22	119.2
O2—C5—C6	125.41 (17)	C19—C23—H23A	109.5
O1—C5—C6	107.31 (15)	C19—C23—H23B	109.5
O3—C6—C5	113.92 (15)	H23A—C23—H23B	109.5
O3—C6—H6A	108.8	C19—C23—H23C	109.5
C5—C6—H6A	108.8	H23A—C23—H23C	109.5
O3—C6—H6B	108.8	H23B—C23—H23C	109.5
C5—C6—H6B	108.8	O4—C24—C25	116.98 (17)
H6A—C6—H6B	107.7	O4—C24—H24A	108.1
O3—C7—C12	114.91 (15)	C25—C24—H24A	108.1
O3—C7—C8	124.60 (16)	O4—C24—H24B	108.1
C12—C7—C8	120.48 (15)	C25—C24—H24B	108.1
C7—C8—C9	119.50 (17)	H24A—C24—H24B	107.3
C7—C8—H8	120.2	O5—C25—O6	126.65 (19)
C9—C8—H8	120.2	O5—C25—C24	120.14 (18)
C10—C9—C8	121.84 (16)	O6—C25—C24	113.20 (16)
C10—C9—H9	119.1	O6—C26—C28	109.1 (2)
C8—C9—H9	119.1	O6—C26—C29	102.79 (19)
C9—C10—C11	116.96 (15)	C28—C26—C29	116.1 (3)
C9—C10—C14	119.77 (15)	O6—C26—C27	109.7 (2)
C11—C10—C14	123.03 (15)	C28—C26—C27	110.2 (3)
C10—C11—C12	123.05 (16)	C29—C26—C27	108.5 (3)
C10—C11—H11	118.5	C26—C27—H27A	109.5
C12—C11—H11	118.5	C26—C27—H27B	109.5
C7—C12—C11	118.11 (15)	H27A—C27—H27B	109.5
C7—C12—C13	120.80 (15)	C26—C27—H27C	109.5
C11—C12—C13	121.08 (16)	H27A—C27—H27C	109.5
C12—C13—H13A	109.5	H27B—C27—H27C	109.5
C12—C13—H13B	109.5	C26—C28—H28A	109.5
H13A—C13—H13B	109.5	C26—C28—H28B	109.5
C12—C13—H13C	109.5	H28A—C28—H28B	109.5
H13A—C13—H13C	109.5	C26—C28—H28C	109.5
H13B—C13—H13C	109.5	H28A—C28—H28C	109.5
C15—C14—C17	106.90 (16)	H28B—C28—H28C	109.5
C15—C14—C10	111.80 (15)	C26—C29—H29A	109.5
C17—C14—C10	111.47 (14)	C26—C29—H29B	109.5
C15—C14—C16	108.36 (18)	H29A—C29—H29B	109.5
C17—C14—C16	111.53 (15)	C26—C29—H29C	109.5
C10—C14—C16	106.79 (15)	H29A—C29—H29C	109.5
C14—C15—H15A	109.5	H29B—C29—H29C	109.5

C5—O1—C1—C4	−62.9 (2)	C15—C14—C17—C18	−95.7 (2)
C5—O1—C1—C2	178.6 (2)	C10—C14—C17—C18	141.89 (16)
C5—O1—C1—C3	60.2 (3)	C16—C14—C17—C18	22.6 (2)
C1—O1—C5—O2	0.6 (3)	C15—C14—C17—C22	79.1 (2)
C1—O1—C5—C6	179.73 (16)	C10—C14—C17—C22	−43.3 (2)
C7—O3—C6—C5	−80.1 (2)	C16—C14—C17—C22	−162.58 (17)
O2—C5—C6—O3	5.4 (3)	C22—C17—C18—C19	−0.6 (3)
O1—C5—C6—O3	−173.69 (15)	C14—C17—C18—C19	174.44 (15)
C6—O3—C7—C12	−177.31 (15)	C17—C18—C19—C20	0.6 (3)
C6—O3—C7—C8	3.2 (3)	C17—C18—C19—C23	−178.41 (17)
O3—C7—C8—C9	178.89 (17)	C24—O4—C20—C21	−8.0 (3)
C12—C7—C8—C9	−0.6 (3)	C24—O4—C20—C19	170.98 (16)
C7—C8—C9—C10	−1.5 (3)	C18—C19—C20—C21	0.0 (3)
C8—C9—C10—C11	2.3 (3)	C23—C19—C20—C21	178.97 (18)
C8—C9—C10—C14	−172.32 (17)	C18—C19—C20—O4	−179.11 (15)
C9—C10—C11—C12	−1.1 (3)	C23—C19—C20—O4	−0.1 (2)
C14—C10—C11—C12	173.34 (16)	O4—C20—C21—C22	178.45 (17)
O3—C7—C12—C11	−177.78 (14)	C19—C20—C21—C22	−0.5 (3)
C8—C7—C12—C11	1.8 (3)	C20—C21—C22—C17	0.6 (3)
O3—C7—C12—C13	0.7 (2)	C18—C17—C22—C21	0.0 (3)
C8—C7—C12—C13	−179.79 (18)	C14—C17—C22—C21	−175.09 (17)
C10—C11—C12—C7	−0.9 (3)	C20—O4—C24—C25	82.9 (2)
C10—C11—C12—C13	−179.34 (17)	C26—O6—C25—O5	1.7 (4)
C9—C10—C14—C15	−176.28 (18)	C26—O6—C25—C24	−179.7 (2)
C11—C10—C14—C15	9.4 (3)	O4—C24—C25—O5	168.5 (2)
C9—C10—C14—C17	−56.7 (2)	O4—C24—C25—O6	−10.2 (3)
C11—C10—C14—C17	129.00 (18)	C25—O6—C26—C28	−65.1 (3)
C9—C10—C14—C16	65.4 (2)	C25—O6—C26—C29	171.0 (3)
C11—C10—C14—C16	−109.0 (2)	C25—O6—C26—C27	55.7 (3)

Experimental details

Crystal data
Chemical formula	C₂₉H₄₀O₆
M_r	484.61
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	8.3154 (6), 12.5589 (8), 13.9410 (9)
α, β, γ (°)	101.782 (1), 97.529 (1), 94.156 (1)
V (Å³)	1405.52 (16)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.45 × 0.35 × 0.30

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	13784, 6428, 4482
R_int	0.021
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.060, 0.184, 1.03
No. of reflections	6428
No. of parameters	318
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.35, −0.19

Computer programs: SMART (Bruker, 2002), SAINT (Bruker, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).

Acknowledgements

The authors thank the Higher Education Commission of Pakistan and the University of Malaya for supporting this study.

References

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
Bruker (2002). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Shah, K., Yousuf, S., Raza Shah, M. & Ng, S. W. (2010). Acta Cryst. E66, o1705. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2010). publCIF. In preparation. Google Scholar

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