Dimethyl (1,1′-binaphthyl-2,2′-di­oxy)diacetate

Mustafa, A.; Shah, M.R.; Khatoon, M.; Ng, S.W.

doi:10.1107/S1600536809010824

organic compounds

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ISSN: 2056-9890

Volume 65| Part 4| April 2009| Page o911

doi:10.1107/S1600536809010824

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Dimethyl (1,1′-binaphthyl-2,2′-dioxy)diacetate

Asra Mustafa,^a Muhammad Raza Shah,^a Maimoona Khatoon ^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 20 March 2009; accepted 24 March 2009; online 28 March 2009)

The two naphthyl fused-ring systems in the title compound, C₂₂H₂₆O₆, are aligned at 86.7 (1)°. Weak intermolecular C—H⋯O hydrogen bonding is present in the crystal structure.

Related literature

For the crystal structure of the parent carboxylic acid, see: Wu et al. (2007 ).

Experimental

Crystal data

C₂₆H₂₂O₆
M_r = 430.44
Orthorhombic, P c c n
a = 17.1288 (5) Å
b = 29.439 (1) Å
c = 8.3518 (3) Å
V = 4211.5 (3) Å³
Z = 8
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 123 K
0.27 × 0.12 × 0.05 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: none
17329 measured reflections
3700 independent reflections
2613 reflections with I > 2σ(I)
R_int = 0.069

Refinement

R[F² > 2σ(F²)] = 0.085
wR(F²) = 0.195
S = 1.23
3700 reflections
244 parameters
H-atom parameters constrained
Δρ_max = 0.57 e Å⁻³
Δρ_min = −0.50 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯O6ⁱ	0.95	2.38	3.330 (3)	174
C21—H21A⋯O6ⁱ	0.99	2.48	3.326 (5)	143
C26—H26B⋯O1ⁱⁱ	0.98	2.46	3.338 (6)	149
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) $[-x+{\script{3\over 2}}, y, z-{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2008 ); cell refinement: SAINT (Bruker, 2008); 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, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809010824/xu2498sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809010824/xu2498Isup2.hkl

checkCIF report

Related literature top

For the crystal structure of the parent carboxylic acid, see: Wu et al. (2007).

Experimental top

Potassium carbonate (0.55 g, 4 mmol) and 1,1'-binaphthyl-2,2'-diol (0.29 mg, 1 mmol) in acetone (10 ml) were stirred for 15 minutes. Methyl 2-chloroacetate (0.54 g, 10 mmol) was added and the mixture was stirred at 323 K for 24twenty-four hours. The solvent was removed and the residue was dissolved in a mixture of water (25 ml) and dichloromethane (25 ml). The two phases were separated and the aqueous layer was extracted with dichloromethane. The combined organic phases were dried and the solvent evaporated. The residue was dissolved recrystallized from dichloromethane (0.33 g, 80% yield).

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); 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, 2009).

Figures top

Fig. 1. Thermal ellipsoid plot (Barbour, 2001) plot of C₂₆H₂₂O₆ at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.

Dimethyl (1,1'-binaphthyl-2,2'-dioxy)diacetate top

Crystal data top

C₂₆H₂₂O₆	F(000) = 1808
M_r = 430.44	D_x = 1.358 Mg m⁻³
Orthorhombic, Pccn	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ab 2ac	Cell parameters from 1966 reflections
a = 17.1288 (5) Å	θ = 2.3–21.8°
b = 29.439 (1) Å	µ = 0.10 mm⁻¹
c = 8.3518 (3) Å	T = 123 K
V = 4211.5 (3) Å³	Prism, colorless
Z = 8	0.27 × 0.12 × 0.05 mm

Data collection top

Bruker SMART APEX diffractometer	2613 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.069
Graphite monochromator	θ_max = 25.0°, θ_min = 1.4°
ω scans	h = −19→20
17329 measured reflections	k = −35→34
3700 independent reflections	l = −9→9

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.085	H-atom parameters constrained
wR(F²) = 0.195	w = 1/[σ²(F_o²) + (0.05P)² + 9P] where P = (F_o² + 2F_c²)/3
S = 1.23	(Δ/σ)_max = 0.001
3700 reflections	Δρ_max = 0.57 e Å⁻³
244 parameters	Δρ_min = −0.50 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0039 (6)

Crystal data top

C₂₆H₂₂O₆	V = 4211.5 (3) Å³
M_r = 430.44	Z = 8
Orthorhombic, Pccn	Mo Kα radiation
a = 17.1288 (5) Å	µ = 0.10 mm⁻¹
b = 29.439 (1) Å	T = 123 K
c = 8.3518 (3) Å	0.27 × 0.12 × 0.05 mm

Data collection top

Bruker SMART APEX diffractometer	2613 reflections with I > 2σ(I)
17329 measured reflections	R_int = 0.069
3700 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.085	0 restraints
wR(F²) = 0.195	H-atom parameters constrained
S = 1.23	Δρ_max = 0.57 e Å⁻³
3700 reflections	Δρ_min = −0.50 e Å⁻³
244 parameters

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

	x	y	z	U_iso*/U_eq
O1	0.49537 (14)	0.44569 (9)	0.6224 (3)	0.0253 (7)
O2	0.41229 (16)	0.50497 (10)	0.9571 (4)	0.0349 (8)
O3	0.43431 (17)	0.43116 (9)	0.9055 (4)	0.0334 (7)
O4	0.56053 (15)	0.38327 (10)	0.2796 (4)	0.0331 (7)
O5	0.75115 (16)	0.41527 (10)	0.1635 (4)	0.0367 (8)
O6	0.67299 (16)	0.44878 (10)	0.3437 (4)	0.0351 (8)
C1	0.44243 (9)	0.38011 (6)	0.4970 (3)	0.0247 (9)
C2	0.43217 (11)	0.42447 (6)	0.5501 (3)	0.0232 (9)
C3	0.36353 (12)	0.44760 (5)	0.5150 (3)	0.0260 (9)
H3	0.3565	0.4779	0.5512	0.031*
C4	0.30515 (10)	0.42638 (5)	0.4268 (3)	0.0293 (10)
H4	0.2582	0.4422	0.4028	0.035*
C5	0.31541 (8)	0.38203 (5)	0.3738 (2)	0.0289 (10)
C6	0.38405 (8)	0.35890 (5)	0.4089 (2)	0.0267 (9)
C7	0.39431 (11)	0.31454 (5)	0.3558 (3)	0.0370 (11)
H7	0.4412	0.2987	0.3798	0.044*
C8	0.33593 (14)	0.29333 (6)	0.2677 (3)	0.0478 (13)
H8	0.3429	0.2630	0.2314	0.057*
C9	0.26729 (13)	0.31646 (7)	0.2326 (3)	0.0453 (13)
H9	0.2274	0.3020	0.1723	0.054*
C10	0.25703 (10)	0.36081 (7)	0.2856 (3)	0.0366 (11)
H10	0.2101	0.3766	0.2616	0.044*
C11	0.52100 (10)	0.35656 (7)	0.5345 (2)	0.0251 (9)
C12	0.57926 (12)	0.36020 (7)	0.4193 (2)	0.0278 (10)
C13	0.65175 (11)	0.34032 (8)	0.4455 (2)	0.0334 (11)
H13	0.6916	0.3428	0.3668	0.040*
C14	0.66599 (9)	0.31681 (7)	0.5869 (3)	0.0342 (11)
H14	0.7155	0.3032	0.6048	0.041*
C15	0.60774 (9)	0.31317 (5)	0.7020 (2)	0.0304 (10)
C16	0.53524 (8)	0.33305 (5)	0.6758 (2)	0.0281 (10)
C17	0.47698 (10)	0.32941 (8)	0.7910 (2)	0.0365 (11)
H17	0.4274	0.3430	0.7731	0.044*
C18	0.49122 (14)	0.30589 (8)	0.9323 (2)	0.0446 (13)
H18	0.4514	0.3034	1.0110	0.054*
C19	0.56372 (15)	0.28602 (8)	0.9585 (2)	0.0493 (14)
H19	0.5734	0.2699	1.0551	0.059*
C20	0.62197 (12)	0.28966 (7)	0.8434 (2)	0.0426 (12)
H20	0.6715	0.2761	0.8613	0.051*
C21	0.4810 (2)	0.48465 (13)	0.7182 (5)	0.0251 (9)
H21A	0.4502	0.5067	0.6547	0.030*
H21B	0.5316	0.4991	0.7444	0.030*
C22	0.4379 (2)	0.47498 (14)	0.8724 (5)	0.0277 (10)
C23	0.4005 (3)	0.41876 (16)	1.0604 (5)	0.0378 (11)
H23A	0.3838	0.3869	1.0577	0.057*
H23B	0.3553	0.4382	1.0825	0.057*
H23C	0.4397	0.4229	1.1447	0.057*
C24	0.6217 (2)	0.39136 (15)	0.1669 (5)	0.0312 (10)
H24A	0.5997	0.4056	0.0694	0.037*
H24B	0.6457	0.3621	0.1358	0.037*
C25	0.6833 (2)	0.42214 (14)	0.2373 (5)	0.0279 (10)
C26	0.8161 (3)	0.44240 (17)	0.2228 (6)	0.0441 (13)
H26A	0.8058	0.4746	0.2020	0.066*
H26B	0.8642	0.4333	0.1681	0.066*
H26C	0.8219	0.4376	0.3383	0.066*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0193 (13)	0.0271 (15)	0.0295 (17)	0.0006 (11)	0.0016 (12)	−0.0053 (13)
O2	0.0353 (16)	0.0398 (17)	0.0297 (18)	0.0082 (14)	0.0038 (14)	−0.0048 (15)
O3	0.0429 (17)	0.0302 (16)	0.0271 (17)	−0.0061 (13)	0.0034 (14)	0.0016 (14)
O4	0.0216 (14)	0.0433 (18)	0.0346 (18)	0.0013 (12)	0.0041 (13)	0.0074 (15)
O5	0.0238 (14)	0.0423 (17)	0.044 (2)	−0.0057 (13)	0.0102 (14)	−0.0114 (16)
O6	0.0338 (16)	0.0358 (17)	0.0356 (18)	0.0062 (13)	0.0020 (14)	−0.0068 (16)
C1	0.022 (2)	0.025 (2)	0.027 (2)	0.0001 (16)	0.0015 (17)	0.0037 (19)
C2	0.0209 (19)	0.028 (2)	0.020 (2)	−0.0054 (16)	0.0017 (17)	0.0017 (18)
C3	0.023 (2)	0.029 (2)	0.025 (2)	0.0010 (17)	0.0026 (17)	0.0002 (19)
C4	0.020 (2)	0.036 (2)	0.031 (2)	0.0028 (17)	0.0018 (18)	0.009 (2)
C5	0.022 (2)	0.036 (2)	0.029 (2)	−0.0070 (17)	−0.0004 (18)	0.009 (2)
C6	0.026 (2)	0.027 (2)	0.027 (2)	−0.0061 (16)	0.0037 (18)	0.0028 (19)
C7	0.031 (2)	0.035 (2)	0.045 (3)	−0.0047 (19)	−0.005 (2)	0.002 (2)
C8	0.045 (3)	0.033 (3)	0.065 (4)	−0.015 (2)	−0.005 (3)	0.000 (3)
C9	0.038 (3)	0.045 (3)	0.053 (3)	−0.021 (2)	−0.011 (2)	0.004 (3)
C10	0.025 (2)	0.043 (3)	0.043 (3)	−0.0110 (19)	−0.002 (2)	0.012 (2)
C11	0.023 (2)	0.022 (2)	0.030 (2)	−0.0037 (16)	−0.0040 (18)	−0.0036 (19)
C12	0.025 (2)	0.024 (2)	0.034 (3)	−0.0029 (16)	−0.0050 (19)	−0.001 (2)
C13	0.022 (2)	0.029 (2)	0.049 (3)	−0.0001 (17)	0.000 (2)	−0.006 (2)
C14	0.025 (2)	0.021 (2)	0.056 (3)	0.0032 (17)	−0.011 (2)	−0.003 (2)
C15	0.031 (2)	0.020 (2)	0.041 (3)	0.0019 (17)	−0.012 (2)	−0.003 (2)
C16	0.029 (2)	0.021 (2)	0.034 (3)	−0.0037 (16)	−0.0042 (19)	0.000 (2)
C17	0.040 (3)	0.028 (2)	0.042 (3)	0.0017 (19)	−0.003 (2)	0.005 (2)
C18	0.056 (3)	0.035 (3)	0.043 (3)	0.002 (2)	0.002 (2)	0.011 (2)
C19	0.069 (4)	0.028 (2)	0.051 (3)	0.003 (2)	−0.020 (3)	0.008 (2)
C20	0.043 (3)	0.027 (2)	0.058 (3)	0.005 (2)	−0.015 (3)	−0.005 (2)
C21	0.026 (2)	0.022 (2)	0.027 (2)	−0.0015 (16)	0.0001 (18)	−0.0026 (18)
C22	0.023 (2)	0.034 (2)	0.026 (2)	0.0006 (17)	−0.0042 (18)	−0.001 (2)
C23	0.039 (3)	0.044 (3)	0.030 (3)	−0.010 (2)	0.000 (2)	0.006 (2)
C24	0.026 (2)	0.036 (2)	0.032 (3)	0.0001 (17)	0.0076 (19)	−0.002 (2)
C25	0.030 (2)	0.025 (2)	0.029 (2)	0.0056 (17)	0.0039 (19)	0.003 (2)
C26	0.032 (2)	0.053 (3)	0.046 (3)	−0.011 (2)	0.002 (2)	−0.007 (3)

Geometric parameters (Å, º) top

O1—C2	1.388 (3)	C11—C16	1.3900
O1—C21	1.420 (5)	C12—C13	1.3900
O2—C22	1.213 (5)	C13—C14	1.3900
O3—C22	1.321 (5)	C13—H13	0.9500
O3—C23	1.464 (5)	C14—C15	1.3900
O4—C12	1.388 (3)	C14—H14	0.9500
O4—C24	1.428 (5)	C15—C16	1.3900
O5—C25	1.330 (5)	C15—C20	1.3900
O5—C26	1.456 (5)	C16—C17	1.3900
O6—C25	1.199 (5)	C17—C18	1.3900
C1—C2	1.3900	C17—H17	0.9500
C1—C6	1.3900	C18—C19	1.3900
C2—C3	1.3900	C18—H18	0.9500
C3—C4	1.3900	C19—C20	1.3900
C3—H3	0.9500	C19—H19	0.9500
C4—C5	1.3900	C20—H20	0.9500
C4—H4	0.9500	C21—C22	1.511 (6)
C5—C6	1.3900	C21—H21A	0.9900
C5—C10	1.3900	C21—H21B	0.9900
C6—C7	1.3900	C23—H23A	0.9800
C7—C8	1.3900	C23—H23B	0.9800
C7—H7	0.9500	C23—H23C	0.9800
C8—C9	1.3900	C24—C25	1.511 (6)
C8—H8	0.9500	C24—H24A	0.9900
C9—C10	1.3900	C24—H24B	0.9900
C9—H9	0.9500	C26—H26A	0.9800
C10—H10	0.9500	C26—H26B	0.9800
C11—C12	1.3900	C26—H26C	0.9800

C2—O1—C21	118.3 (2)	C17—C16—C15	120.0
C22—O3—C23	116.5 (3)	C17—C16—C11	120.0
C12—O4—C24	117.8 (3)	C15—C16—C11	120.0
C25—O5—C26	115.2 (3)	C16—C17—C18	120.0
C2—C1—C6	120.0	C16—C17—H17	120.0
O1—C2—C1	117.57 (16)	C18—C17—H17	120.0
O1—C2—C3	122.06 (16)	C19—C18—C17	120.0
C1—C2—C3	120.0	C19—C18—H18	120.0
C4—C3—C2	120.0	C17—C18—H18	120.0
C4—C3—H3	120.0	C18—C19—C20	120.0
C2—C3—H3	120.0	C18—C19—H19	120.0
C3—C4—C5	120.0	C20—C19—H19	120.0
C3—C4—H4	120.0	C19—C20—C15	120.0
C5—C4—H4	120.0	C19—C20—H20	120.0
C6—C5—C4	120.0	C15—C20—H20	120.0
C6—C5—C10	120.0	O1—C21—C22	114.4 (3)
C4—C5—C10	120.0	O1—C21—H21A	108.7
C7—C6—C5	120.0	C22—C21—H21A	108.7
C7—C6—C1	120.0	O1—C21—H21B	108.7
C5—C6—C1	120.0	C22—C21—H21B	108.7
C8—C7—C6	120.0	H21A—C21—H21B	107.6
C8—C7—H7	120.0	O2—C22—O3	124.9 (4)
C6—C7—H7	120.0	O2—C22—C21	122.4 (4)
C7—C8—C9	120.0	O3—C22—C21	112.6 (3)
C7—C8—H8	120.0	O3—C23—H23A	109.5
C9—C8—H8	120.0	O3—C23—H23B	109.5
C10—C9—C8	120.0	H23A—C23—H23B	109.5
C10—C9—H9	120.0	O3—C23—H23C	109.5
C8—C9—H9	120.0	H23A—C23—H23C	109.5
C9—C10—C5	120.0	H23B—C23—H23C	109.5
C9—C10—H10	120.0	O4—C24—C25	110.9 (4)
C5—C10—H10	120.0	O4—C24—H24A	109.5
C12—C11—C16	120.0	C25—C24—H24A	109.5
O4—C12—C13	123.01 (16)	O4—C24—H24B	109.5
O4—C12—C11	116.98 (16)	C25—C24—H24B	109.5
C13—C12—C11	120.0	H24A—C24—H24B	108.0
C12—C13—C14	120.0	O6—C25—O5	124.9 (4)
C12—C13—H13	120.0	O6—C25—C24	125.3 (4)
C14—C13—H13	120.0	O5—C25—C24	109.8 (4)
C15—C14—C13	120.0	O5—C26—H26A	109.5
C15—C14—H14	120.0	O5—C26—H26B	109.5
C13—C14—H14	120.0	H26A—C26—H26B	109.5
C14—C15—C16	120.0	O5—C26—H26C	109.5
C14—C15—C20	120.0	H26A—C26—H26C	109.5
C16—C15—C20	120.0	H26B—C26—H26C	109.5

C21—O1—C2—C1	−161.7 (2)	C11—C12—C13—C14	0.0
C21—O1—C2—C3	25.3 (4)	C12—C13—C14—C15	0.0
C6—C1—C2—O1	−173.2 (2)	C13—C14—C15—C16	0.0
C6—C1—C2—C3	0.0	C13—C14—C15—C20	180.0
O1—C2—C3—C4	172.9 (2)	C14—C15—C16—C17	180.0
C1—C2—C3—C4	0.0	C20—C15—C16—C17	0.0
C2—C3—C4—C5	0.0	C14—C15—C16—C11	0.0
C3—C4—C5—C6	0.0	C20—C15—C16—C11	180.0
C3—C4—C5—C10	180.0	C12—C11—C16—C17	180.0
C4—C5—C6—C7	180.0	C12—C11—C16—C15	0.0
C10—C5—C6—C7	0.0	C15—C16—C17—C18	0.0
C4—C5—C6—C1	0.0	C11—C16—C17—C18	180.0
C10—C5—C6—C1	180.0	C16—C17—C18—C19	0.0
C2—C1—C6—C7	180.0	C17—C18—C19—C20	0.0
C2—C1—C6—C5	0.0	C18—C19—C20—C15	0.0
C5—C6—C7—C8	0.0	C14—C15—C20—C19	180.0
C1—C6—C7—C8	180.0	C16—C15—C20—C19	0.0
C6—C7—C8—C9	0.0	C2—O1—C21—C22	68.8 (4)
C7—C8—C9—C10	0.0	C23—O3—C22—O2	−3.5 (6)
C8—C9—C10—C5	0.0	C23—O3—C22—C21	174.1 (3)
C6—C5—C10—C9	0.0	O1—C21—C22—O2	−170.2 (4)
C4—C5—C10—C9	180.0	O1—C21—C22—O3	12.1 (5)
C24—O4—C12—C13	−7.6 (4)	C12—O4—C24—C25	−64.1 (4)
C24—O4—C12—C11	173.8 (2)	C26—O5—C25—O6	1.1 (6)
C16—C11—C12—O4	178.6 (2)	C26—O5—C25—C24	−178.8 (4)
C16—C11—C12—C13	0.0	O4—C24—C25—O6	−24.5 (6)
O4—C12—C13—C14	−178.5 (2)	O4—C24—C25—O5	155.4 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O6ⁱ	0.95	2.38	3.330 (3)	174
C21—H21A···O6ⁱ	0.99	2.48	3.326 (5)	143
C26—H26B···O1ⁱⁱ	0.98	2.46	3.338 (6)	149

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+3/2, y, z−1/2.

Experimental details

Crystal data
Chemical formula	C₂₆H₂₂O₆
M_r	430.44
Crystal system, space group	Orthorhombic, Pccn
Temperature (K)	123
a, b, c (Å)	17.1288 (5), 29.439 (1), 8.3518 (3)
V (Å³)	4211.5 (3)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.27 × 0.12 × 0.05

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	17329, 3700, 2613
R_int	0.069
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.085, 0.195, 1.23
No. of reflections	3700
No. of parameters	244
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.57, −0.50

Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O6ⁱ	0.95	2.38	3.330 (3)	174
C21—H21A···O6ⁱ	0.99	2.48	3.326 (5)	143
C26—H26B···O1ⁱⁱ	0.98	2.46	3.338 (6)	149

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+3/2, y, z−1/2.

Acknowledgements

We 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 (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2009). publCIF. In preparation. Google Scholar
Wu, Y.-M., Cao, G.-Q., Qian, M.-Y. & Zhu, H.-J. (2007). Acta Cryst. E63, o3446. Web of Science CSD CrossRef IUCr Journals Google Scholar