Methyl (2′-hydroxy­biphenyl-2-yl­oxy)acetate

Rabnawaz, M.; Khan, B.; Shah, M.R.; Anis, I.; Ng, S.W.

doi:10.1107/S1600536809011362

organic compounds

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ISSN: 2056-9890

Volume 65| Part 4| April 2009| Page o931

doi:10.1107/S1600536809011362

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Methyl (2′-hydroxybiphenyl-2-yloxy)acetate

Muhammad Rabnawaz,^a Burhan Khan,^a Muhammad Raza Shah,^a Itrat Anis ^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 26 March 2009; accepted 27 March 2009; online 31 March 2009)

The three independent molecules of the title compound, C₁₅H₁₄O₄, have similar orientations of their aromatic rings, the dihedral angles between the rings being 57.0 (1), 58.1 (1) and 58.2 (1)°. In each molecule, the hydroxy group forms an intramolecular hydrogen bond to the carbonyl O atom, forming an S(10) ring motif.

Related literature

Only one of the two hydroxy groups of 2,2′-biphenyl-2,2′-diol underwent reaction to yield the mono-acetate title compound; a similar synthesis with tert-butyl bromoacetate gave di-tert-butyl 2,2′-(biphenyl-2,2′-diyldioxy)diacetate; see: Ali et al. (2008 ).

Experimental

Crystal data

C₁₅H₁₄O₄
M_r = 258.26
Monoclinic, P 2₁
a = 10.9221 (2) Å
b = 7.5592 (1) Å
c = 23.3470 (4) Å
β = 98.465 (1)°
V = 1906.58 (5) Å³
Z = 6
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 125 K
0.45 × 0.40 × 0.10 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: none
13392 measured reflections
4639 independent reflections
4276 reflections with I > 2σ(I)
R_int = 0.025

Refinement

R[F² > 2σ(F²)] = 0.031
wR(F²) = 0.090
S = 1.05
4639 reflections
529 parameters
4 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.21 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
O1—H1⋯O4	0.84 (1)	2.14 (2)	2.832 (2)	140 (3)
O5—H5⋯O8	0.84 (1)	2.12 (2)	2.856 (2)	145 (3)
O9—H9⋯O12	0.84 (1)	2.03 (2)	2.768 (2)	146 (3)

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/S1600536809011362/tk2406sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809011362/tk2406Isup2.hkl

checkCIF report

Related literature top

Only one of the two hydroxy groups of 2,2'-biphenyl-2,2'-diol underwent reaction to yield the mono-acetate title compound; a similar synthesis with tert-butyl bromoacetate gave di-tert-butyl 2,2'-(biphenyl-2,2'-diyldioxy)diacetate; see: Ali et al. (2008).

Experimental top

Potassium carbonate (0.69 g, 5 mmol) and 2,2'-biphenyl-2,2'-diol (0.93 mg, 5 mmol) in acetone (15 ml) were stirred for 20 minutes. Methyl 2-chloroacetate (0.22 g, 2 mmol) was added and the mixture was stirred at 323 K for 24 h. 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 (0.20 g, 30% 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 the independent molecules of C₁₄H₁₄O₄ at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.

Methyl (2'-hydroxybiphenyl-2-yloxy)acetate top

Crystal data top

C₁₅H₁₄O₄	F(000) = 816
M_r = 258.26	D_x = 1.350 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 6021 reflections
a = 10.9221 (2) Å	θ = 2.2–28.2°
b = 7.5592 (1) Å	µ = 0.10 mm⁻¹
c = 23.3470 (4) Å	T = 125 K
β = 98.465 (1)°	Block, colorless
V = 1906.58 (5) Å³	0.45 × 0.40 × 0.10 mm
Z = 6

Data collection top

Bruker SMART APEX diffractometer	4276 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.025
Graphite monochromator	θ_max = 27.5°, θ_min = 0.9°
ω scans	h = −14→14
13392 measured reflections	k = −9→9
4639 independent reflections	l = −29→29

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)] = 0.031	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.090	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ²(F_o²) + (0.0585P)² + 0.1469P] where P = (F_o² + 2F_c²)/3
4639 reflections	(Δ/σ)_max = 0.001
529 parameters	Δρ_max = 0.21 e Å⁻³
4 restraints	Δρ_min = −0.19 e Å⁻³

Crystal data top

C₁₅H₁₄O₄	V = 1906.58 (5) Å³
M_r = 258.26	Z = 6
Monoclinic, P2₁	Mo Kα radiation
a = 10.9221 (2) Å	µ = 0.10 mm⁻¹
b = 7.5592 (1) Å	T = 125 K
c = 23.3470 (4) Å	0.45 × 0.40 × 0.10 mm
β = 98.465 (1)°

Data collection top

Bruker SMART APEX diffractometer	4276 reflections with I > 2σ(I)
13392 measured reflections	R_int = 0.025
4639 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.031	4 restraints
wR(F²) = 0.090	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	Δρ_max = 0.21 e Å⁻³
4639 reflections	Δρ_min = −0.19 e Å⁻³
529 parameters

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

	x	y	z	U_iso*/U_eq
O1	0.71809 (15)	0.5002 (2)	0.08306 (7)	0.0281 (3)
O2	0.91376 (15)	0.3602 (2)	0.17515 (7)	0.0308 (3)
O3	0.96802 (18)	0.7736 (2)	0.24751 (8)	0.0403 (4)
O4	0.89043 (18)	0.7116 (2)	0.15551 (8)	0.0415 (4)
O5	0.29708 (14)	0.6042 (2)	0.28983 (7)	0.0257 (3)
O6	0.50479 (13)	0.7375 (2)	0.23064 (6)	0.0246 (3)
O7	0.64332 (15)	0.3191 (2)	0.21256 (7)	0.0325 (4)
O8	0.45161 (15)	0.3890 (2)	0.22975 (7)	0.0326 (4)
O9	0.78564 (13)	0.4140 (2)	0.49000 (6)	0.0245 (3)
O10	0.62876 (12)	0.3744 (2)	0.37611 (6)	0.0221 (3)
O11	0.35403 (13)	0.3858 (2)	0.44207 (6)	0.0255 (3)
O12	0.54504 (14)	0.2888 (2)	0.47747 (7)	0.0296 (3)
C1	0.69918 (19)	0.3221 (3)	0.07567 (8)	0.0224 (4)
C2	0.5761 (2)	0.2690 (3)	0.06425 (9)	0.0252 (4)
H2	0.5121	0.3547	0.0632	0.030*
C3	0.5456 (2)	0.0929 (3)	0.05441 (9)	0.0284 (5)
H3	0.4612	0.0583	0.0465	0.034*
C4	0.6386 (2)	−0.0334 (3)	0.05609 (9)	0.0270 (5)
H4	0.6182	−0.1548	0.0501	0.032*
C5	0.7613 (2)	0.0199 (3)	0.06665 (9)	0.0246 (4)
H5A	0.8245	−0.0666	0.0672	0.029*
C6	0.79483 (19)	0.1973 (3)	0.07651 (8)	0.0215 (4)
C7	0.92776 (19)	0.2461 (3)	0.08343 (9)	0.0244 (4)
C8	0.9994 (2)	0.1989 (3)	0.04093 (10)	0.0322 (5)
H8	0.9619	0.1358	0.0077	0.039*
C9	1.1239 (2)	0.2421 (4)	0.04609 (13)	0.0405 (6)
H9A	1.1714	0.2073	0.0170	0.049*
C10	1.1781 (2)	0.3356 (4)	0.09370 (14)	0.0447 (7)
H10	1.2628	0.3683	0.0966	0.054*
C11	1.1116 (2)	0.3832 (3)	0.13741 (13)	0.0387 (6)
H11	1.1500	0.4476	0.1701	0.046*
C12	0.9875 (2)	0.3348 (3)	0.13249 (10)	0.0280 (4)
C13	0.9554 (3)	0.4753 (3)	0.22167 (11)	0.0371 (6)
H13A	1.0446	0.4547	0.2350	0.045*
H13B	0.9099	0.4502	0.2544	0.045*
C14	0.9352 (2)	0.6664 (3)	0.20314 (10)	0.0291 (5)
C15	0.9453 (3)	0.9596 (4)	0.23748 (14)	0.0428 (6)
H15A	1.0083	1.0285	0.2622	0.064*
H15B	0.8631	0.9898	0.2467	0.064*
H15C	0.9489	0.9870	0.1967	0.064*
C16	0.28539 (18)	0.7837 (3)	0.29631 (9)	0.0220 (4)
C17	0.26399 (19)	0.8417 (3)	0.35043 (9)	0.0263 (4)
H17	0.2647	0.7595	0.3813	0.032*
C18	0.24159 (19)	1.0195 (3)	0.35955 (10)	0.0289 (5)
H18	0.2261	1.0585	0.3965	0.035*
C19	0.24183 (19)	1.1403 (3)	0.31486 (10)	0.0268 (5)
H19	0.2255	1.2618	0.3208	0.032*
C20	0.26621 (18)	1.0815 (3)	0.26122 (9)	0.0231 (4)
H20	0.2681	1.1648	0.2309	0.028*
C21	0.28794 (17)	0.9034 (3)	0.25074 (8)	0.0200 (4)
C22	0.30778 (18)	0.8449 (3)	0.19194 (8)	0.0206 (4)
C23	0.2185 (2)	0.8801 (3)	0.14421 (9)	0.0266 (4)
H23	0.1457	0.9427	0.1495	0.032*
C24	0.2343 (2)	0.8250 (3)	0.08907 (9)	0.0325 (5)
H24	0.1724	0.8496	0.0570	0.039*
C25	0.3398 (2)	0.7348 (3)	0.08079 (9)	0.0305 (5)
H25	0.3496	0.6953	0.0431	0.037*
C26	0.4317 (2)	0.7011 (3)	0.12718 (9)	0.0264 (4)
H26	0.5049	0.6398	0.1214	0.032*
C27	0.41578 (19)	0.7577 (3)	0.18212 (9)	0.0217 (4)
C28	0.6021 (2)	0.6175 (3)	0.22633 (10)	0.0278 (5)
H28A	0.6669	0.6309	0.2604	0.033*
H28B	0.6396	0.6445	0.1912	0.033*
C29	0.5549 (2)	0.4293 (3)	0.22318 (9)	0.0250 (4)
C30	0.6092 (3)	0.1327 (3)	0.20667 (12)	0.0405 (6)
H30A	0.6684	0.0702	0.1863	0.061*
H30B	0.5259	0.1221	0.1846	0.061*
H30C	0.6102	0.0806	0.2452	0.061*
C31	0.87045 (17)	0.4344 (3)	0.45300 (8)	0.0198 (4)
C32	0.95512 (19)	0.5718 (3)	0.46605 (9)	0.0240 (4)
H32	0.9501	0.6454	0.4986	0.029*
C33	1.0468 (2)	0.6019 (3)	0.43176 (10)	0.0275 (5)
H33	1.1029	0.6975	0.4404	0.033*
C34	1.05647 (19)	0.4928 (3)	0.38491 (10)	0.0283 (5)
H34	1.1191	0.5127	0.3614	0.034*
C35	0.97378 (18)	0.3543 (3)	0.37285 (9)	0.0236 (4)
H35	0.9818	0.2782	0.3412	0.028*
C36	0.87894 (17)	0.3229 (3)	0.40565 (8)	0.0193 (4)
C37	0.79318 (18)	0.1725 (3)	0.38900 (8)	0.0200 (4)
C38	0.83849 (19)	0.0013 (3)	0.38485 (9)	0.0239 (4)
H38	0.9249	−0.0195	0.3942	0.029*
C39	0.7602 (2)	−0.1396 (3)	0.36738 (9)	0.0265 (4)
H39	0.7925	−0.2554	0.3647	0.032*
C40	0.6336 (2)	−0.1087 (3)	0.35387 (8)	0.0262 (4)
H40	0.5794	−0.2045	0.3423	0.031*
C41	0.5858 (2)	0.0602 (3)	0.35716 (9)	0.0236 (4)
H41	0.4993	0.0801	0.3478	0.028*
C42	0.66532 (18)	0.2002 (3)	0.37430 (8)	0.0201 (4)
C43	0.50249 (18)	0.4079 (3)	0.38061 (8)	0.0236 (4)
H43A	0.4491	0.3424	0.3498	0.028*
H43B	0.4852	0.5357	0.3748	0.028*
C44	0.47157 (18)	0.3521 (3)	0.43910 (9)	0.0224 (4)
C45	0.3151 (2)	0.3513 (3)	0.49790 (9)	0.0308 (5)
H45A	0.2274	0.3814	0.4961	0.046*
H45B	0.3645	0.4234	0.5277	0.046*
H45C	0.3273	0.2257	0.5076	0.046*
H1	0.7905 (13)	0.520 (4)	0.0996 (12)	0.042 (8)*
H5	0.335 (2)	0.578 (4)	0.2620 (9)	0.041 (8)*
H9	0.726 (2)	0.350 (4)	0.4765 (14)	0.057 (10)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0296 (8)	0.0196 (7)	0.0321 (8)	0.0012 (6)	−0.0059 (7)	−0.0010 (6)
O2	0.0364 (8)	0.0248 (8)	0.0291 (8)	−0.0027 (7)	−0.0023 (7)	−0.0023 (7)
O3	0.0474 (10)	0.0352 (10)	0.0352 (9)	−0.0064 (8)	−0.0041 (8)	−0.0110 (8)
O4	0.0560 (11)	0.0263 (9)	0.0356 (10)	−0.0014 (8)	−0.0153 (8)	0.0008 (7)
O5	0.0293 (8)	0.0234 (8)	0.0261 (8)	0.0014 (6)	0.0100 (6)	0.0045 (6)
O6	0.0228 (7)	0.0254 (8)	0.0252 (7)	0.0010 (6)	0.0024 (6)	−0.0064 (6)
O7	0.0353 (8)	0.0285 (8)	0.0353 (8)	0.0088 (7)	0.0108 (7)	−0.0002 (7)
O8	0.0338 (8)	0.0261 (8)	0.0405 (9)	−0.0011 (7)	0.0143 (7)	0.0006 (7)
O9	0.0245 (7)	0.0295 (8)	0.0198 (7)	−0.0006 (6)	0.0039 (6)	−0.0026 (6)
O10	0.0181 (6)	0.0238 (7)	0.0242 (7)	0.0004 (6)	0.0025 (5)	0.0043 (6)
O11	0.0221 (7)	0.0315 (8)	0.0238 (7)	0.0007 (6)	0.0068 (6)	−0.0009 (6)
O12	0.0261 (7)	0.0383 (9)	0.0240 (7)	0.0024 (7)	0.0020 (6)	0.0073 (7)
C1	0.0300 (10)	0.0207 (10)	0.0158 (9)	−0.0006 (8)	0.0009 (8)	0.0010 (7)
C2	0.0273 (10)	0.0279 (11)	0.0198 (10)	0.0021 (9)	0.0013 (8)	−0.0001 (8)
C3	0.0290 (11)	0.0322 (12)	0.0234 (10)	−0.0065 (9)	0.0023 (8)	0.0002 (9)
C4	0.0375 (12)	0.0209 (10)	0.0224 (10)	−0.0057 (9)	0.0033 (9)	−0.0012 (8)
C5	0.0332 (11)	0.0217 (10)	0.0188 (10)	0.0022 (9)	0.0036 (8)	0.0019 (8)
C6	0.0275 (10)	0.0208 (10)	0.0155 (9)	−0.0008 (8)	0.0002 (8)	0.0018 (8)
C7	0.0266 (10)	0.0192 (10)	0.0269 (10)	0.0027 (8)	0.0023 (8)	0.0080 (8)
C8	0.0363 (12)	0.0282 (11)	0.0330 (12)	0.0058 (10)	0.0083 (10)	0.0102 (10)
C9	0.0351 (13)	0.0334 (13)	0.0562 (16)	0.0079 (11)	0.0173 (12)	0.0196 (12)
C10	0.0292 (12)	0.0296 (13)	0.076 (2)	−0.0025 (10)	0.0090 (13)	0.0175 (13)
C11	0.0311 (11)	0.0216 (11)	0.0594 (16)	−0.0034 (10)	−0.0062 (11)	0.0084 (11)
C12	0.0300 (10)	0.0174 (9)	0.0348 (11)	−0.0003 (9)	−0.0015 (9)	0.0062 (9)
C13	0.0480 (14)	0.0317 (13)	0.0265 (11)	0.0004 (11)	−0.0118 (10)	−0.0005 (10)
C14	0.0269 (11)	0.0286 (12)	0.0300 (12)	−0.0030 (9)	−0.0016 (9)	−0.0043 (9)
C15	0.0384 (14)	0.0340 (14)	0.0566 (17)	−0.0058 (11)	0.0088 (12)	−0.0198 (12)
C16	0.0176 (9)	0.0238 (10)	0.0246 (10)	−0.0014 (8)	0.0028 (8)	−0.0001 (8)
C17	0.0228 (9)	0.0353 (12)	0.0216 (10)	−0.0054 (9)	0.0059 (8)	0.0011 (9)
C18	0.0224 (10)	0.0399 (12)	0.0258 (10)	−0.0074 (9)	0.0083 (8)	−0.0131 (9)
C19	0.0196 (9)	0.0272 (11)	0.0340 (12)	−0.0033 (8)	0.0050 (9)	−0.0108 (9)
C20	0.0189 (9)	0.0224 (10)	0.0269 (10)	−0.0008 (8)	−0.0001 (8)	−0.0013 (8)
C21	0.0160 (8)	0.0242 (10)	0.0196 (9)	−0.0006 (8)	0.0014 (7)	−0.0019 (8)
C22	0.0249 (9)	0.0170 (9)	0.0197 (9)	−0.0037 (8)	0.0023 (7)	−0.0002 (7)
C23	0.0323 (11)	0.0203 (10)	0.0251 (10)	−0.0007 (9)	−0.0025 (8)	0.0009 (8)
C24	0.0522 (14)	0.0225 (11)	0.0198 (10)	−0.0049 (10)	−0.0050 (9)	0.0022 (8)
C25	0.0533 (14)	0.0198 (10)	0.0192 (10)	−0.0063 (10)	0.0082 (9)	−0.0013 (8)
C26	0.0375 (12)	0.0195 (10)	0.0242 (10)	−0.0046 (9)	0.0108 (9)	−0.0030 (8)
C27	0.0273 (10)	0.0169 (9)	0.0209 (9)	−0.0049 (8)	0.0040 (8)	−0.0008 (7)
C28	0.0202 (10)	0.0314 (11)	0.0316 (11)	0.0023 (9)	0.0031 (9)	−0.0072 (9)
C29	0.0275 (10)	0.0301 (11)	0.0177 (9)	0.0020 (9)	0.0044 (8)	−0.0016 (8)
C30	0.0626 (17)	0.0237 (11)	0.0387 (13)	0.0098 (12)	0.0189 (12)	0.0034 (10)
C31	0.0180 (9)	0.0219 (9)	0.0182 (9)	0.0030 (8)	−0.0016 (7)	0.0005 (7)
C32	0.0228 (10)	0.0245 (10)	0.0232 (10)	0.0014 (8)	−0.0016 (8)	−0.0058 (8)
C33	0.0208 (10)	0.0276 (11)	0.0331 (11)	−0.0038 (9)	0.0007 (8)	−0.0063 (9)
C34	0.0227 (10)	0.0318 (12)	0.0316 (11)	−0.0034 (9)	0.0077 (9)	−0.0054 (9)
C35	0.0212 (9)	0.0260 (10)	0.0235 (10)	0.0014 (8)	0.0032 (8)	−0.0031 (8)
C36	0.0178 (9)	0.0192 (9)	0.0194 (9)	0.0017 (8)	−0.0021 (7)	0.0005 (7)
C37	0.0224 (9)	0.0222 (10)	0.0152 (9)	−0.0021 (8)	0.0027 (7)	0.0006 (7)
C38	0.0256 (10)	0.0251 (10)	0.0201 (9)	0.0017 (9)	0.0006 (8)	−0.0007 (8)
C39	0.0360 (11)	0.0219 (10)	0.0215 (10)	−0.0008 (9)	0.0035 (9)	−0.0003 (8)
C40	0.0358 (11)	0.0271 (11)	0.0150 (9)	−0.0108 (10)	0.0018 (8)	−0.0011 (8)
C41	0.0237 (10)	0.0284 (11)	0.0181 (9)	−0.0054 (8)	0.0013 (8)	0.0015 (8)
C42	0.0228 (9)	0.0237 (10)	0.0138 (9)	−0.0014 (8)	0.0028 (7)	0.0024 (8)
C43	0.0178 (9)	0.0290 (11)	0.0232 (9)	0.0023 (8)	0.0006 (7)	0.0060 (8)
C44	0.0220 (9)	0.0212 (10)	0.0239 (10)	−0.0022 (8)	0.0030 (8)	0.0004 (8)
C45	0.0336 (11)	0.0356 (12)	0.0258 (10)	−0.0028 (10)	0.0125 (9)	−0.0006 (9)

Geometric parameters (Å, º) top

O1—C1	1.369 (3)	C17—H17	0.9500
O1—H1	0.842 (10)	C18—C19	1.387 (3)
O2—C12	1.383 (3)	C18—H18	0.9500
O2—C13	1.414 (3)	C19—C20	1.391 (3)
O3—C14	1.322 (3)	C19—H19	0.9500
O3—C15	1.441 (3)	C20—C21	1.394 (3)
O4—C14	1.197 (3)	C20—H20	0.9500
O5—C16	1.373 (3)	C21—C22	1.488 (3)
O5—H5	0.843 (10)	C22—C23	1.394 (3)
O6—C27	1.388 (3)	C22—C27	1.400 (3)
O6—C28	1.412 (3)	C23—C24	1.388 (3)
O7—C29	1.326 (3)	C23—H23	0.9500
O7—C30	1.458 (3)	C24—C25	1.376 (4)
O8—C29	1.200 (3)	C24—H24	0.9500
O9—C31	1.365 (2)	C25—C26	1.388 (3)
O9—H9	0.839 (10)	C25—H25	0.9500
O10—C42	1.379 (3)	C26—C27	1.387 (3)
O10—C43	1.421 (2)	C26—H26	0.9500
O11—C44	1.321 (2)	C28—C29	1.511 (3)
O11—C45	1.453 (2)	C28—H28A	0.9900
O12—C44	1.210 (3)	C28—H28B	0.9900
C1—C2	1.391 (3)	C30—H30A	0.9800
C1—C6	1.406 (3)	C30—H30B	0.9800
C2—C3	1.383 (3)	C30—H30C	0.9800
C2—H2	0.9500	C31—C32	1.394 (3)
C3—C4	1.390 (3)	C31—C36	1.404 (3)
C3—H3	0.9500	C32—C33	1.389 (3)
C4—C5	1.387 (3)	C32—H32	0.9500
C4—H4	0.9500	C33—C34	1.387 (3)
C5—C6	1.400 (3)	C33—H33	0.9500
C5—H5A	0.9500	C34—C35	1.384 (3)
C6—C7	1.484 (3)	C34—H34	0.9500
C7—C8	1.397 (3)	C35—C36	1.396 (3)
C7—C12	1.402 (3)	C35—H35	0.9500
C8—C9	1.386 (3)	C36—C37	1.488 (3)
C8—H8	0.9500	C37—C38	1.394 (3)
C9—C10	1.376 (4)	C37—C42	1.404 (3)
C9—H9A	0.9500	C38—C39	1.389 (3)
C10—C11	1.384 (4)	C38—H38	0.9500
C10—H10	0.9500	C39—C40	1.391 (3)
C11—C12	1.393 (3)	C39—H39	0.9500
C11—H11	0.9500	C40—C41	1.386 (3)
C13—C14	1.515 (3)	C40—H40	0.9500
C13—H13A	0.9900	C41—C42	1.390 (3)
C13—H13B	0.9900	C41—H41	0.9500
C15—H15A	0.9800	C43—C44	1.514 (3)
C15—H15B	0.9800	C43—H43A	0.9900
C15—H15C	0.9800	C43—H43B	0.9900
C16—C17	1.389 (3)	C45—H45A	0.9800
C16—C21	1.400 (3)	C45—H45B	0.9800
C17—C18	1.388 (3)	C45—H45C	0.9800

C1—O1—H1	110 (2)	C24—C23—C22	121.1 (2)
C12—O2—C13	118.89 (19)	C24—C23—H23	119.4
C14—O3—C15	116.7 (2)	C22—C23—H23	119.4
C16—O5—H5	112 (2)	C25—C24—C23	120.0 (2)
C27—O6—C28	117.16 (16)	C25—C24—H24	120.0
C29—O7—C30	116.2 (2)	C23—C24—H24	120.0
C31—O9—H9	113 (2)	C24—C25—C26	120.4 (2)
C42—O10—C43	117.45 (16)	C24—C25—H25	119.8
C44—O11—C45	115.29 (17)	C26—C25—H25	119.8
O1—C1—C2	115.58 (19)	C27—C26—C25	119.3 (2)
O1—C1—C6	124.08 (19)	C27—C26—H26	120.3
C2—C1—C6	120.3 (2)	C25—C26—H26	120.3
C3—C2—C1	120.8 (2)	O6—C27—C26	123.53 (19)
C3—C2—H2	119.6	O6—C27—C22	115.08 (17)
C1—C2—H2	119.6	C26—C27—C22	121.37 (19)
C2—C3—C4	120.0 (2)	O6—C28—C29	110.71 (17)
C2—C3—H3	120.0	O6—C28—H28A	109.5
C4—C3—H3	120.0	C29—C28—H28A	109.5
C5—C4—C3	119.2 (2)	O6—C28—H28B	109.5
C5—C4—H4	120.4	C29—C28—H28B	109.5
C3—C4—H4	120.4	H28A—C28—H28B	108.1
C4—C5—C6	122.0 (2)	O8—C29—O7	126.0 (2)
C4—C5—H5A	119.0	O8—C29—C28	123.6 (2)
C6—C5—H5A	119.0	O7—C29—C28	110.38 (18)
C5—C6—C1	117.69 (19)	O7—C30—H30A	109.5
C5—C6—C7	118.99 (19)	O7—C30—H30B	109.5
C1—C6—C7	123.20 (19)	H30A—C30—H30B	109.5
C8—C7—C12	117.4 (2)	O7—C30—H30C	109.5
C8—C7—C6	120.0 (2)	H30A—C30—H30C	109.5
C12—C7—C6	122.56 (19)	H30B—C30—H30C	109.5
C9—C8—C7	121.5 (2)	O9—C31—C32	115.83 (18)
C9—C8—H8	119.2	O9—C31—C36	124.07 (18)
C7—C8—H8	119.2	C32—C31—C36	120.05 (18)
C10—C9—C8	119.4 (2)	C33—C32—C31	120.46 (19)
C10—C9—H9A	120.3	C33—C32—H32	119.8
C8—C9—H9A	120.3	C31—C32—H32	119.8
C9—C10—C11	121.3 (2)	C34—C33—C32	120.1 (2)
C9—C10—H10	119.3	C34—C33—H33	119.9
C11—C10—H10	119.3	C32—C33—H33	119.9
C10—C11—C12	118.7 (3)	C35—C34—C33	119.1 (2)
C10—C11—H11	120.6	C35—C34—H34	120.4
C12—C11—H11	120.6	C33—C34—H34	120.4
O2—C12—C11	124.5 (2)	C34—C35—C36	122.13 (19)
O2—C12—C7	113.84 (18)	C34—C35—H35	118.9
C11—C12—C7	121.5 (2)	C36—C35—H35	118.9
O2—C13—C14	110.53 (18)	C35—C36—C31	118.03 (18)
O2—C13—H13A	109.5	C35—C36—C37	118.44 (18)
C14—C13—H13A	109.5	C31—C36—C37	123.53 (17)
O2—C13—H13B	109.5	C38—C37—C42	118.14 (19)
C14—C13—H13B	109.5	C38—C37—C36	120.75 (18)
H13A—C13—H13B	108.1	C42—C37—C36	121.04 (18)
O4—C14—O3	125.4 (2)	C39—C38—C37	121.50 (19)
O4—C14—C13	124.1 (2)	C39—C38—H38	119.2
O3—C14—C13	110.4 (2)	C37—C38—H38	119.2
O3—C15—H15A	109.5	C38—C39—C40	119.1 (2)
O3—C15—H15B	109.5	C38—C39—H39	120.5
H15A—C15—H15B	109.5	C40—C39—H39	120.5
O3—C15—H15C	109.5	C41—C40—C39	120.8 (2)
H15A—C15—H15C	109.5	C41—C40—H40	119.6
H15B—C15—H15C	109.5	C39—C40—H40	119.6
O5—C16—C17	116.29 (19)	C40—C41—C42	119.49 (19)
O5—C16—C21	122.86 (19)	C40—C41—H41	120.3
C17—C16—C21	120.8 (2)	C42—C41—H41	120.3
C18—C17—C16	120.2 (2)	O10—C42—C41	124.37 (18)
C18—C17—H17	119.9	O10—C42—C37	114.63 (18)
C16—C17—H17	119.9	C41—C42—C37	120.9 (2)
C19—C18—C17	120.1 (2)	O10—C43—C44	111.40 (16)
C19—C18—H18	119.9	O10—C43—H43A	109.3
C17—C18—H18	119.9	C44—C43—H43A	109.3
C18—C19—C20	119.3 (2)	O10—C43—H43B	109.3
C18—C19—H19	120.4	C44—C43—H43B	109.3
C20—C19—H19	120.4	H43A—C43—H43B	108.0
C19—C20—C21	121.8 (2)	O12—C44—O11	125.55 (18)
C19—C20—H20	119.1	O12—C44—C43	124.49 (18)
C21—C20—H20	119.1	O11—C44—C43	109.95 (17)
C20—C21—C16	117.88 (18)	O11—C45—H45A	109.5
C20—C21—C22	120.02 (18)	O11—C45—H45B	109.5
C16—C21—C22	122.04 (18)	H45A—C45—H45B	109.5
C23—C22—C27	117.76 (18)	O11—C45—H45C	109.5
C23—C22—C21	120.09 (18)	H45A—C45—H45C	109.5
C27—C22—C21	122.14 (17)	H45B—C45—H45C	109.5

O1—C1—C2—C3	178.20 (19)	C22—C23—C24—C25	−0.3 (3)
C6—C1—C2—C3	1.0 (3)	C23—C24—C25—C26	−1.2 (3)
C1—C2—C3—C4	0.2 (3)	C24—C25—C26—C27	0.6 (3)
C2—C3—C4—C5	−1.2 (3)	C28—O6—C27—C26	−15.6 (3)
C3—C4—C5—C6	0.9 (3)	C28—O6—C27—C22	166.09 (18)
C4—C5—C6—C1	0.3 (3)	C25—C26—C27—O6	−176.90 (19)
C4—C5—C6—C7	−175.76 (18)	C25—C26—C27—C22	1.3 (3)
O1—C1—C6—C5	−178.19 (19)	C23—C22—C27—O6	175.67 (18)
C2—C1—C6—C5	−1.2 (3)	C21—C22—C27—O6	−2.9 (3)
O1—C1—C6—C7	−2.3 (3)	C23—C22—C27—C26	−2.7 (3)
C2—C1—C6—C7	174.66 (18)	C21—C22—C27—C26	178.75 (19)
C5—C6—C7—C8	54.1 (3)	C27—O6—C28—C29	−69.6 (2)
C1—C6—C7—C8	−121.7 (2)	C30—O7—C29—O8	2.0 (3)
C5—C6—C7—C12	−123.8 (2)	C30—O7—C29—C28	−178.2 (2)
C1—C6—C7—C12	60.4 (3)	O6—C28—C29—O8	−7.3 (3)
C12—C7—C8—C9	−1.8 (3)	O6—C28—C29—O7	172.94 (18)
C6—C7—C8—C9	−179.8 (2)	O9—C31—C32—C33	178.82 (19)
C7—C8—C9—C10	−0.9 (4)	C36—C31—C32—C33	1.3 (3)
C8—C9—C10—C11	1.9 (4)	C31—C32—C33—C34	−1.4 (3)
C9—C10—C11—C12	−0.1 (4)	C32—C33—C34—C35	0.1 (3)
C13—O2—C12—C11	14.5 (3)	C33—C34—C35—C36	1.4 (3)
C13—O2—C12—C7	−168.49 (19)	C34—C35—C36—C31	−1.4 (3)
C10—C11—C12—O2	174.1 (2)	C34—C35—C36—C37	179.1 (2)
C10—C11—C12—C7	−2.7 (3)	O9—C31—C36—C35	−177.18 (18)
C8—C7—C12—O2	−173.51 (19)	C32—C31—C36—C35	0.1 (3)
C6—C7—C12—O2	4.5 (3)	O9—C31—C36—C37	2.2 (3)
C8—C7—C12—C11	3.6 (3)	C32—C31—C36—C37	179.51 (19)
C6—C7—C12—C11	−178.4 (2)	C35—C36—C37—C38	56.0 (3)
C12—O2—C13—C14	78.3 (3)	C31—C36—C37—C38	−123.5 (2)
C15—O3—C14—O4	1.3 (4)	C35—C36—C37—C42	−120.9 (2)
C15—O3—C14—C13	−175.5 (2)	C31—C36—C37—C42	59.7 (3)
O2—C13—C14—O4	−0.2 (4)	C42—C37—C38—C39	−0.8 (3)
O2—C13—C14—O3	176.7 (2)	C36—C37—C38—C39	−177.68 (19)
O5—C16—C17—C18	−175.07 (19)	C37—C38—C39—C40	−0.1 (3)
C21—C16—C17—C18	1.7 (3)	C38—C39—C40—C41	0.6 (3)
C16—C17—C18—C19	−0.7 (3)	C39—C40—C41—C42	−0.2 (3)
C17—C18—C19—C20	−0.8 (3)	C43—O10—C42—C41	22.8 (3)
C18—C19—C20—C21	1.4 (3)	C43—O10—C42—C37	−159.91 (16)
C19—C20—C21—C16	−0.4 (3)	C40—C41—C42—O10	176.38 (18)
C19—C20—C21—C22	177.11 (18)	C40—C41—C42—C37	−0.8 (3)
O5—C16—C21—C20	175.43 (19)	C38—C37—C42—O10	−176.20 (16)
C17—C16—C21—C20	−1.1 (3)	C36—C37—C42—O10	0.7 (3)
O5—C16—C21—C22	−2.0 (3)	C38—C37—C42—C41	1.2 (3)
C17—C16—C21—C22	−178.58 (18)	C36—C37—C42—C41	178.14 (18)
C20—C21—C22—C23	−56.7 (3)	C42—O10—C43—C44	68.5 (2)
C16—C21—C22—C23	120.7 (2)	C45—O11—C44—O12	3.6 (3)
C20—C21—C22—C27	121.8 (2)	C45—O11—C44—C43	−175.28 (18)
C16—C21—C22—C27	−60.7 (3)	O10—C43—C44—O12	0.7 (3)
C27—C22—C23—C24	2.2 (3)	O10—C43—C44—O11	179.63 (17)
C21—C22—C23—C24	−179.24 (19)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O4	0.84 (1)	2.14 (2)	2.832 (2)	140 (3)
O5—H5···O8	0.84 (1)	2.12 (2)	2.856 (2)	145 (3)
O9—H9···O12	0.84 (1)	2.03 (2)	2.768 (2)	146 (3)

Experimental details

Crystal data
Chemical formula	C₁₅H₁₄O₄
M_r	258.26
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	125
a, b, c (Å)	10.9221 (2), 7.5592 (1), 23.3470 (4)
β (°)	98.465 (1)
V (Å³)	1906.58 (5)
Z	6
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.45 × 0.40 × 0.10

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	13392, 4639, 4276
R_int	0.025
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.031, 0.090, 1.05
No. of reflections	4639
No. of parameters	529
No. of restraints	4
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.21, −0.19

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
O1—H1···O4	0.84 (1)	2.14 (2)	2.832 (2)	140 (3)
O5—H5···O8	0.84 (1)	2.12 (2)	2.856 (2)	145 (3)
O9—H9···O12	0.84 (1)	2.03 (2)	2.768 (2)	146 (3)

Acknowledgements

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

References

Ali, Q., Ibad, F., Shah, M. R. & VanDerveer, D. (2008). Acta Cryst. E64, o1408. Web of Science CSD CrossRef IUCr Journals Google Scholar
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