organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890

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

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[Ali, Q., Ibad, F., Shah, M. R. & VanDerveer, D. (2008). Acta Cryst. E64, o1408.]).

[Scheme 1]

Experimental

Crystal data
  • C15H14O4

  • Mr = 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)

  • Rint = 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

  • Δρmax = 0.21 e Å−3

  • Δρmin = −0.19 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA 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[Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2008[Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: X-SEED (Barbour, 2001[Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.]); software used to prepare material for publication: publCIF (Westrip, 2009[Westrip, S. P. (2009). publCIF. In preparation.]).

Supporting information


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).

Refinement top

Carbon-bound H-atoms were placed in calculated positions (C—H 0.93 to 0.99 Å) and were included in the refinement in the riding model approximation, with U(H) set to 1.2 to 1.5Ueq(C). The hydroxy H-atoms were refined with a distance restraint of O–H 0.84±0.01 Å; their temperature factors were refined. In the absence of significant anomalous scattering effects, 3704 Friedel pairs were averaged in the final refinement.

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
[Figure 1] 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
C15H14O4F(000) = 816
Mr = 258.26Dx = 1.350 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 6021 reflections
a = 10.9221 (2) Åθ = 2.2–28.2°
b = 7.5592 (1) ŵ = 0.10 mm1
c = 23.3470 (4) ÅT = 125 K
β = 98.465 (1)°Block, colorless
V = 1906.58 (5) Å30.45 × 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 tubeRint = 0.025
Graphite monochromatorθmax = 27.5°, θmin = 0.9°
ω scansh = 1414
13392 measured reflectionsk = 99
4639 independent reflectionsl = 2929
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.031Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.090H atoms treated by a mixture of independent and constrained refinement
S = 1.05 w = 1/[σ2(Fo2) + (0.0585P)2 + 0.1469P]
where P = (Fo2 + 2Fc2)/3
4639 reflections(Δ/σ)max = 0.001
529 parametersΔρmax = 0.21 e Å3
4 restraintsΔρmin = 0.19 e Å3
Crystal data top
C15H14O4V = 1906.58 (5) Å3
Mr = 258.26Z = 6
Monoclinic, P21Mo Kα radiation
a = 10.9221 (2) ŵ = 0.10 mm1
b = 7.5592 (1) ÅT = 125 K
c = 23.3470 (4) Å0.45 × 0.40 × 0.10 mm
β = 98.465 (1)°
Data collection top
Bruker SMART APEX
diffractometer
4276 reflections with I > 2σ(I)
13392 measured reflectionsRint = 0.025
4639 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0314 restraints
wR(F2) = 0.090H atoms treated by a mixture of independent and constrained refinement
S = 1.05Δρmax = 0.21 e Å3
4639 reflectionsΔρmin = 0.19 e Å3
529 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.71809 (15)0.5002 (2)0.08306 (7)0.0281 (3)
O20.91376 (15)0.3602 (2)0.17515 (7)0.0308 (3)
O30.96802 (18)0.7736 (2)0.24751 (8)0.0403 (4)
O40.89043 (18)0.7116 (2)0.15551 (8)0.0415 (4)
O50.29708 (14)0.6042 (2)0.28983 (7)0.0257 (3)
O60.50479 (13)0.7375 (2)0.23064 (6)0.0246 (3)
O70.64332 (15)0.3191 (2)0.21256 (7)0.0325 (4)
O80.45161 (15)0.3890 (2)0.22975 (7)0.0326 (4)
O90.78564 (13)0.4140 (2)0.49000 (6)0.0245 (3)
O100.62876 (12)0.3744 (2)0.37611 (6)0.0221 (3)
O110.35403 (13)0.3858 (2)0.44207 (6)0.0255 (3)
O120.54504 (14)0.2888 (2)0.47747 (7)0.0296 (3)
C10.69918 (19)0.3221 (3)0.07567 (8)0.0224 (4)
C20.5761 (2)0.2690 (3)0.06425 (9)0.0252 (4)
H20.51210.35470.06320.030*
C30.5456 (2)0.0929 (3)0.05441 (9)0.0284 (5)
H30.46120.05830.04650.034*
C40.6386 (2)0.0334 (3)0.05609 (9)0.0270 (5)
H40.61820.15480.05010.032*
C50.7613 (2)0.0199 (3)0.06665 (9)0.0246 (4)
H5A0.82450.06660.06720.029*
C60.79483 (19)0.1973 (3)0.07651 (8)0.0215 (4)
C70.92776 (19)0.2461 (3)0.08343 (9)0.0244 (4)
C80.9994 (2)0.1989 (3)0.04093 (10)0.0322 (5)
H80.96190.13580.00770.039*
C91.1239 (2)0.2421 (4)0.04609 (13)0.0405 (6)
H9A1.17140.20730.01700.049*
C101.1781 (2)0.3356 (4)0.09370 (14)0.0447 (7)
H101.26280.36830.09660.054*
C111.1116 (2)0.3832 (3)0.13741 (13)0.0387 (6)
H111.15000.44760.17010.046*
C120.9875 (2)0.3348 (3)0.13249 (10)0.0280 (4)
C130.9554 (3)0.4753 (3)0.22167 (11)0.0371 (6)
H13A1.04460.45470.23500.045*
H13B0.90990.45020.25440.045*
C140.9352 (2)0.6664 (3)0.20314 (10)0.0291 (5)
C150.9453 (3)0.9596 (4)0.23748 (14)0.0428 (6)
H15A1.00831.02850.26220.064*
H15B0.86310.98980.24670.064*
H15C0.94890.98700.19670.064*
C160.28539 (18)0.7837 (3)0.29631 (9)0.0220 (4)
C170.26399 (19)0.8417 (3)0.35043 (9)0.0263 (4)
H170.26470.75950.38130.032*
C180.24159 (19)1.0195 (3)0.35955 (10)0.0289 (5)
H180.22611.05850.39650.035*
C190.24183 (19)1.1403 (3)0.31486 (10)0.0268 (5)
H190.22551.26180.32080.032*
C200.26621 (18)1.0815 (3)0.26122 (9)0.0231 (4)
H200.26811.16480.23090.028*
C210.28794 (17)0.9034 (3)0.25074 (8)0.0200 (4)
C220.30778 (18)0.8449 (3)0.19194 (8)0.0206 (4)
C230.2185 (2)0.8801 (3)0.14421 (9)0.0266 (4)
H230.14570.94270.14950.032*
C240.2343 (2)0.8250 (3)0.08907 (9)0.0325 (5)
H240.17240.84960.05700.039*
C250.3398 (2)0.7348 (3)0.08079 (9)0.0305 (5)
H250.34960.69530.04310.037*
C260.4317 (2)0.7011 (3)0.12718 (9)0.0264 (4)
H260.50490.63980.12140.032*
C270.41578 (19)0.7577 (3)0.18212 (9)0.0217 (4)
C280.6021 (2)0.6175 (3)0.22633 (10)0.0278 (5)
H28A0.66690.63090.26040.033*
H28B0.63960.64450.19120.033*
C290.5549 (2)0.4293 (3)0.22318 (9)0.0250 (4)
C300.6092 (3)0.1327 (3)0.20667 (12)0.0405 (6)
H30A0.66840.07020.18630.061*
H30B0.52590.12210.18460.061*
H30C0.61020.08060.24520.061*
C310.87045 (17)0.4344 (3)0.45300 (8)0.0198 (4)
C320.95512 (19)0.5718 (3)0.46605 (9)0.0240 (4)
H320.95010.64540.49860.029*
C331.0468 (2)0.6019 (3)0.43176 (10)0.0275 (5)
H331.10290.69750.44040.033*
C341.05647 (19)0.4928 (3)0.38491 (10)0.0283 (5)
H341.11910.51270.36140.034*
C350.97378 (18)0.3543 (3)0.37285 (9)0.0236 (4)
H350.98180.27820.34120.028*
C360.87894 (17)0.3229 (3)0.40565 (8)0.0193 (4)
C370.79318 (18)0.1725 (3)0.38900 (8)0.0200 (4)
C380.83849 (19)0.0013 (3)0.38485 (9)0.0239 (4)
H380.92490.01950.39420.029*
C390.7602 (2)0.1396 (3)0.36738 (9)0.0265 (4)
H390.79250.25540.36470.032*
C400.6336 (2)0.1087 (3)0.35387 (8)0.0262 (4)
H400.57940.20450.34230.031*
C410.5858 (2)0.0602 (3)0.35716 (9)0.0236 (4)
H410.49930.08010.34780.028*
C420.66532 (18)0.2002 (3)0.37430 (8)0.0201 (4)
C430.50249 (18)0.4079 (3)0.38061 (8)0.0236 (4)
H43A0.44910.34240.34980.028*
H43B0.48520.53570.37480.028*
C440.47157 (18)0.3521 (3)0.43910 (9)0.0224 (4)
C450.3151 (2)0.3513 (3)0.49790 (9)0.0308 (5)
H45A0.22740.38140.49610.046*
H45B0.36450.42340.52770.046*
H45C0.32730.22570.50760.046*
H10.7905 (13)0.520 (4)0.0996 (12)0.042 (8)*
H50.335 (2)0.578 (4)0.2620 (9)0.041 (8)*
H90.726 (2)0.350 (4)0.4765 (14)0.057 (10)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0296 (8)0.0196 (7)0.0321 (8)0.0012 (6)0.0059 (7)0.0010 (6)
O20.0364 (8)0.0248 (8)0.0291 (8)0.0027 (7)0.0023 (7)0.0023 (7)
O30.0474 (10)0.0352 (10)0.0352 (9)0.0064 (8)0.0041 (8)0.0110 (8)
O40.0560 (11)0.0263 (9)0.0356 (10)0.0014 (8)0.0153 (8)0.0008 (7)
O50.0293 (8)0.0234 (8)0.0261 (8)0.0014 (6)0.0100 (6)0.0045 (6)
O60.0228 (7)0.0254 (8)0.0252 (7)0.0010 (6)0.0024 (6)0.0064 (6)
O70.0353 (8)0.0285 (8)0.0353 (8)0.0088 (7)0.0108 (7)0.0002 (7)
O80.0338 (8)0.0261 (8)0.0405 (9)0.0011 (7)0.0143 (7)0.0006 (7)
O90.0245 (7)0.0295 (8)0.0198 (7)0.0006 (6)0.0039 (6)0.0026 (6)
O100.0181 (6)0.0238 (7)0.0242 (7)0.0004 (6)0.0025 (5)0.0043 (6)
O110.0221 (7)0.0315 (8)0.0238 (7)0.0007 (6)0.0068 (6)0.0009 (6)
O120.0261 (7)0.0383 (9)0.0240 (7)0.0024 (7)0.0020 (6)0.0073 (7)
C10.0300 (10)0.0207 (10)0.0158 (9)0.0006 (8)0.0009 (8)0.0010 (7)
C20.0273 (10)0.0279 (11)0.0198 (10)0.0021 (9)0.0013 (8)0.0001 (8)
C30.0290 (11)0.0322 (12)0.0234 (10)0.0065 (9)0.0023 (8)0.0002 (9)
C40.0375 (12)0.0209 (10)0.0224 (10)0.0057 (9)0.0033 (9)0.0012 (8)
C50.0332 (11)0.0217 (10)0.0188 (10)0.0022 (9)0.0036 (8)0.0019 (8)
C60.0275 (10)0.0208 (10)0.0155 (9)0.0008 (8)0.0002 (8)0.0018 (8)
C70.0266 (10)0.0192 (10)0.0269 (10)0.0027 (8)0.0023 (8)0.0080 (8)
C80.0363 (12)0.0282 (11)0.0330 (12)0.0058 (10)0.0083 (10)0.0102 (10)
C90.0351 (13)0.0334 (13)0.0562 (16)0.0079 (11)0.0173 (12)0.0196 (12)
C100.0292 (12)0.0296 (13)0.076 (2)0.0025 (10)0.0090 (13)0.0175 (13)
C110.0311 (11)0.0216 (11)0.0594 (16)0.0034 (10)0.0062 (11)0.0084 (11)
C120.0300 (10)0.0174 (9)0.0348 (11)0.0003 (9)0.0015 (9)0.0062 (9)
C130.0480 (14)0.0317 (13)0.0265 (11)0.0004 (11)0.0118 (10)0.0005 (10)
C140.0269 (11)0.0286 (12)0.0300 (12)0.0030 (9)0.0016 (9)0.0043 (9)
C150.0384 (14)0.0340 (14)0.0566 (17)0.0058 (11)0.0088 (12)0.0198 (12)
C160.0176 (9)0.0238 (10)0.0246 (10)0.0014 (8)0.0028 (8)0.0001 (8)
C170.0228 (9)0.0353 (12)0.0216 (10)0.0054 (9)0.0059 (8)0.0011 (9)
C180.0224 (10)0.0399 (12)0.0258 (10)0.0074 (9)0.0083 (8)0.0131 (9)
C190.0196 (9)0.0272 (11)0.0340 (12)0.0033 (8)0.0050 (9)0.0108 (9)
C200.0189 (9)0.0224 (10)0.0269 (10)0.0008 (8)0.0001 (8)0.0013 (8)
C210.0160 (8)0.0242 (10)0.0196 (9)0.0006 (8)0.0014 (7)0.0019 (8)
C220.0249 (9)0.0170 (9)0.0197 (9)0.0037 (8)0.0023 (7)0.0002 (7)
C230.0323 (11)0.0203 (10)0.0251 (10)0.0007 (9)0.0025 (8)0.0009 (8)
C240.0522 (14)0.0225 (11)0.0198 (10)0.0049 (10)0.0050 (9)0.0022 (8)
C250.0533 (14)0.0198 (10)0.0192 (10)0.0063 (10)0.0082 (9)0.0013 (8)
C260.0375 (12)0.0195 (10)0.0242 (10)0.0046 (9)0.0108 (9)0.0030 (8)
C270.0273 (10)0.0169 (9)0.0209 (9)0.0049 (8)0.0040 (8)0.0008 (7)
C280.0202 (10)0.0314 (11)0.0316 (11)0.0023 (9)0.0031 (9)0.0072 (9)
C290.0275 (10)0.0301 (11)0.0177 (9)0.0020 (9)0.0044 (8)0.0016 (8)
C300.0626 (17)0.0237 (11)0.0387 (13)0.0098 (12)0.0189 (12)0.0034 (10)
C310.0180 (9)0.0219 (9)0.0182 (9)0.0030 (8)0.0016 (7)0.0005 (7)
C320.0228 (10)0.0245 (10)0.0232 (10)0.0014 (8)0.0016 (8)0.0058 (8)
C330.0208 (10)0.0276 (11)0.0331 (11)0.0038 (9)0.0007 (8)0.0063 (9)
C340.0227 (10)0.0318 (12)0.0316 (11)0.0034 (9)0.0077 (9)0.0054 (9)
C350.0212 (9)0.0260 (10)0.0235 (10)0.0014 (8)0.0032 (8)0.0031 (8)
C360.0178 (9)0.0192 (9)0.0194 (9)0.0017 (8)0.0021 (7)0.0005 (7)
C370.0224 (9)0.0222 (10)0.0152 (9)0.0021 (8)0.0027 (7)0.0006 (7)
C380.0256 (10)0.0251 (10)0.0201 (9)0.0017 (9)0.0006 (8)0.0007 (8)
C390.0360 (11)0.0219 (10)0.0215 (10)0.0008 (9)0.0035 (9)0.0003 (8)
C400.0358 (11)0.0271 (11)0.0150 (9)0.0108 (10)0.0018 (8)0.0011 (8)
C410.0237 (10)0.0284 (11)0.0181 (9)0.0054 (8)0.0013 (8)0.0015 (8)
C420.0228 (9)0.0237 (10)0.0138 (9)0.0014 (8)0.0028 (7)0.0024 (8)
C430.0178 (9)0.0290 (11)0.0232 (9)0.0023 (8)0.0006 (7)0.0060 (8)
C440.0220 (9)0.0212 (10)0.0239 (10)0.0022 (8)0.0030 (8)0.0004 (8)
C450.0336 (11)0.0356 (12)0.0258 (10)0.0028 (10)0.0125 (9)0.0006 (9)
Geometric parameters (Å, º) top
O1—C11.369 (3)C17—H170.9500
O1—H10.842 (10)C18—C191.387 (3)
O2—C121.383 (3)C18—H180.9500
O2—C131.414 (3)C19—C201.391 (3)
O3—C141.322 (3)C19—H190.9500
O3—C151.441 (3)C20—C211.394 (3)
O4—C141.197 (3)C20—H200.9500
O5—C161.373 (3)C21—C221.488 (3)
O5—H50.843 (10)C22—C231.394 (3)
O6—C271.388 (3)C22—C271.400 (3)
O6—C281.412 (3)C23—C241.388 (3)
O7—C291.326 (3)C23—H230.9500
O7—C301.458 (3)C24—C251.376 (4)
O8—C291.200 (3)C24—H240.9500
O9—C311.365 (2)C25—C261.388 (3)
O9—H90.839 (10)C25—H250.9500
O10—C421.379 (3)C26—C271.387 (3)
O10—C431.421 (2)C26—H260.9500
O11—C441.321 (2)C28—C291.511 (3)
O11—C451.453 (2)C28—H28A0.9900
O12—C441.210 (3)C28—H28B0.9900
C1—C21.391 (3)C30—H30A0.9800
C1—C61.406 (3)C30—H30B0.9800
C2—C31.383 (3)C30—H30C0.9800
C2—H20.9500C31—C321.394 (3)
C3—C41.390 (3)C31—C361.404 (3)
C3—H30.9500C32—C331.389 (3)
C4—C51.387 (3)C32—H320.9500
C4—H40.9500C33—C341.387 (3)
C5—C61.400 (3)C33—H330.9500
C5—H5A0.9500C34—C351.384 (3)
C6—C71.484 (3)C34—H340.9500
C7—C81.397 (3)C35—C361.396 (3)
C7—C121.402 (3)C35—H350.9500
C8—C91.386 (3)C36—C371.488 (3)
C8—H80.9500C37—C381.394 (3)
C9—C101.376 (4)C37—C421.404 (3)
C9—H9A0.9500C38—C391.389 (3)
C10—C111.384 (4)C38—H380.9500
C10—H100.9500C39—C401.391 (3)
C11—C121.393 (3)C39—H390.9500
C11—H110.9500C40—C411.386 (3)
C13—C141.515 (3)C40—H400.9500
C13—H13A0.9900C41—C421.390 (3)
C13—H13B0.9900C41—H410.9500
C15—H15A0.9800C43—C441.514 (3)
C15—H15B0.9800C43—H43A0.9900
C15—H15C0.9800C43—H43B0.9900
C16—C171.389 (3)C45—H45A0.9800
C16—C211.400 (3)C45—H45B0.9800
C17—C181.388 (3)C45—H45C0.9800
C1—O1—H1110 (2)C24—C23—C22121.1 (2)
C12—O2—C13118.89 (19)C24—C23—H23119.4
C14—O3—C15116.7 (2)C22—C23—H23119.4
C16—O5—H5112 (2)C25—C24—C23120.0 (2)
C27—O6—C28117.16 (16)C25—C24—H24120.0
C29—O7—C30116.2 (2)C23—C24—H24120.0
C31—O9—H9113 (2)C24—C25—C26120.4 (2)
C42—O10—C43117.45 (16)C24—C25—H25119.8
C44—O11—C45115.29 (17)C26—C25—H25119.8
O1—C1—C2115.58 (19)C27—C26—C25119.3 (2)
O1—C1—C6124.08 (19)C27—C26—H26120.3
C2—C1—C6120.3 (2)C25—C26—H26120.3
C3—C2—C1120.8 (2)O6—C27—C26123.53 (19)
C3—C2—H2119.6O6—C27—C22115.08 (17)
C1—C2—H2119.6C26—C27—C22121.37 (19)
C2—C3—C4120.0 (2)O6—C28—C29110.71 (17)
C2—C3—H3120.0O6—C28—H28A109.5
C4—C3—H3120.0C29—C28—H28A109.5
C5—C4—C3119.2 (2)O6—C28—H28B109.5
C5—C4—H4120.4C29—C28—H28B109.5
C3—C4—H4120.4H28A—C28—H28B108.1
C4—C5—C6122.0 (2)O8—C29—O7126.0 (2)
C4—C5—H5A119.0O8—C29—C28123.6 (2)
C6—C5—H5A119.0O7—C29—C28110.38 (18)
C5—C6—C1117.69 (19)O7—C30—H30A109.5
C5—C6—C7118.99 (19)O7—C30—H30B109.5
C1—C6—C7123.20 (19)H30A—C30—H30B109.5
C8—C7—C12117.4 (2)O7—C30—H30C109.5
C8—C7—C6120.0 (2)H30A—C30—H30C109.5
C12—C7—C6122.56 (19)H30B—C30—H30C109.5
C9—C8—C7121.5 (2)O9—C31—C32115.83 (18)
C9—C8—H8119.2O9—C31—C36124.07 (18)
C7—C8—H8119.2C32—C31—C36120.05 (18)
C10—C9—C8119.4 (2)C33—C32—C31120.46 (19)
C10—C9—H9A120.3C33—C32—H32119.8
C8—C9—H9A120.3C31—C32—H32119.8
C9—C10—C11121.3 (2)C34—C33—C32120.1 (2)
C9—C10—H10119.3C34—C33—H33119.9
C11—C10—H10119.3C32—C33—H33119.9
C10—C11—C12118.7 (3)C35—C34—C33119.1 (2)
C10—C11—H11120.6C35—C34—H34120.4
C12—C11—H11120.6C33—C34—H34120.4
O2—C12—C11124.5 (2)C34—C35—C36122.13 (19)
O2—C12—C7113.84 (18)C34—C35—H35118.9
C11—C12—C7121.5 (2)C36—C35—H35118.9
O2—C13—C14110.53 (18)C35—C36—C31118.03 (18)
O2—C13—H13A109.5C35—C36—C37118.44 (18)
C14—C13—H13A109.5C31—C36—C37123.53 (17)
O2—C13—H13B109.5C38—C37—C42118.14 (19)
C14—C13—H13B109.5C38—C37—C36120.75 (18)
H13A—C13—H13B108.1C42—C37—C36121.04 (18)
O4—C14—O3125.4 (2)C39—C38—C37121.50 (19)
O4—C14—C13124.1 (2)C39—C38—H38119.2
O3—C14—C13110.4 (2)C37—C38—H38119.2
O3—C15—H15A109.5C38—C39—C40119.1 (2)
O3—C15—H15B109.5C38—C39—H39120.5
H15A—C15—H15B109.5C40—C39—H39120.5
O3—C15—H15C109.5C41—C40—C39120.8 (2)
H15A—C15—H15C109.5C41—C40—H40119.6
H15B—C15—H15C109.5C39—C40—H40119.6
O5—C16—C17116.29 (19)C40—C41—C42119.49 (19)
O5—C16—C21122.86 (19)C40—C41—H41120.3
C17—C16—C21120.8 (2)C42—C41—H41120.3
C18—C17—C16120.2 (2)O10—C42—C41124.37 (18)
C18—C17—H17119.9O10—C42—C37114.63 (18)
C16—C17—H17119.9C41—C42—C37120.9 (2)
C19—C18—C17120.1 (2)O10—C43—C44111.40 (16)
C19—C18—H18119.9O10—C43—H43A109.3
C17—C18—H18119.9C44—C43—H43A109.3
C18—C19—C20119.3 (2)O10—C43—H43B109.3
C18—C19—H19120.4C44—C43—H43B109.3
C20—C19—H19120.4H43A—C43—H43B108.0
C19—C20—C21121.8 (2)O12—C44—O11125.55 (18)
C19—C20—H20119.1O12—C44—C43124.49 (18)
C21—C20—H20119.1O11—C44—C43109.95 (17)
C20—C21—C16117.88 (18)O11—C45—H45A109.5
C20—C21—C22120.02 (18)O11—C45—H45B109.5
C16—C21—C22122.04 (18)H45A—C45—H45B109.5
C23—C22—C27117.76 (18)O11—C45—H45C109.5
C23—C22—C21120.09 (18)H45A—C45—H45C109.5
C27—C22—C21122.14 (17)H45B—C45—H45C109.5
O1—C1—C2—C3178.20 (19)C22—C23—C24—C250.3 (3)
C6—C1—C2—C31.0 (3)C23—C24—C25—C261.2 (3)
C1—C2—C3—C40.2 (3)C24—C25—C26—C270.6 (3)
C2—C3—C4—C51.2 (3)C28—O6—C27—C2615.6 (3)
C3—C4—C5—C60.9 (3)C28—O6—C27—C22166.09 (18)
C4—C5—C6—C10.3 (3)C25—C26—C27—O6176.90 (19)
C4—C5—C6—C7175.76 (18)C25—C26—C27—C221.3 (3)
O1—C1—C6—C5178.19 (19)C23—C22—C27—O6175.67 (18)
C2—C1—C6—C51.2 (3)C21—C22—C27—O62.9 (3)
O1—C1—C6—C72.3 (3)C23—C22—C27—C262.7 (3)
C2—C1—C6—C7174.66 (18)C21—C22—C27—C26178.75 (19)
C5—C6—C7—C854.1 (3)C27—O6—C28—C2969.6 (2)
C1—C6—C7—C8121.7 (2)C30—O7—C29—O82.0 (3)
C5—C6—C7—C12123.8 (2)C30—O7—C29—C28178.2 (2)
C1—C6—C7—C1260.4 (3)O6—C28—C29—O87.3 (3)
C12—C7—C8—C91.8 (3)O6—C28—C29—O7172.94 (18)
C6—C7—C8—C9179.8 (2)O9—C31—C32—C33178.82 (19)
C7—C8—C9—C100.9 (4)C36—C31—C32—C331.3 (3)
C8—C9—C10—C111.9 (4)C31—C32—C33—C341.4 (3)
C9—C10—C11—C120.1 (4)C32—C33—C34—C350.1 (3)
C13—O2—C12—C1114.5 (3)C33—C34—C35—C361.4 (3)
C13—O2—C12—C7168.49 (19)C34—C35—C36—C311.4 (3)
C10—C11—C12—O2174.1 (2)C34—C35—C36—C37179.1 (2)
C10—C11—C12—C72.7 (3)O9—C31—C36—C35177.18 (18)
C8—C7—C12—O2173.51 (19)C32—C31—C36—C350.1 (3)
C6—C7—C12—O24.5 (3)O9—C31—C36—C372.2 (3)
C8—C7—C12—C113.6 (3)C32—C31—C36—C37179.51 (19)
C6—C7—C12—C11178.4 (2)C35—C36—C37—C3856.0 (3)
C12—O2—C13—C1478.3 (3)C31—C36—C37—C38123.5 (2)
C15—O3—C14—O41.3 (4)C35—C36—C37—C42120.9 (2)
C15—O3—C14—C13175.5 (2)C31—C36—C37—C4259.7 (3)
O2—C13—C14—O40.2 (4)C42—C37—C38—C390.8 (3)
O2—C13—C14—O3176.7 (2)C36—C37—C38—C39177.68 (19)
O5—C16—C17—C18175.07 (19)C37—C38—C39—C400.1 (3)
C21—C16—C17—C181.7 (3)C38—C39—C40—C410.6 (3)
C16—C17—C18—C190.7 (3)C39—C40—C41—C420.2 (3)
C17—C18—C19—C200.8 (3)C43—O10—C42—C4122.8 (3)
C18—C19—C20—C211.4 (3)C43—O10—C42—C37159.91 (16)
C19—C20—C21—C160.4 (3)C40—C41—C42—O10176.38 (18)
C19—C20—C21—C22177.11 (18)C40—C41—C42—C370.8 (3)
O5—C16—C21—C20175.43 (19)C38—C37—C42—O10176.20 (16)
C17—C16—C21—C201.1 (3)C36—C37—C42—O100.7 (3)
O5—C16—C21—C222.0 (3)C38—C37—C42—C411.2 (3)
C17—C16—C21—C22178.58 (18)C36—C37—C42—C41178.14 (18)
C20—C21—C22—C2356.7 (3)C42—O10—C43—C4468.5 (2)
C16—C21—C22—C23120.7 (2)C45—O11—C44—O123.6 (3)
C20—C21—C22—C27121.8 (2)C45—O11—C44—C43175.28 (18)
C16—C21—C22—C2760.7 (3)O10—C43—C44—O120.7 (3)
C27—C22—C23—C242.2 (3)O10—C43—C44—O11179.63 (17)
C21—C22—C23—C24179.24 (19)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O40.84 (1)2.14 (2)2.832 (2)140 (3)
O5—H5···O80.84 (1)2.12 (2)2.856 (2)145 (3)
O9—H9···O120.84 (1)2.03 (2)2.768 (2)146 (3)

Experimental details

Crystal data
Chemical formulaC15H14O4
Mr258.26
Crystal system, space groupMonoclinic, P21
Temperature (K)125
a, b, c (Å)10.9221 (2), 7.5592 (1), 23.3470 (4)
β (°) 98.465 (1)
V3)1906.58 (5)
Z6
Radiation typeMo Kα
µ (mm1)0.10
Crystal size (mm)0.45 × 0.40 × 0.10
Data collection
DiffractometerBruker SMART APEX
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
13392, 4639, 4276
Rint0.025
(sin θ/λ)max1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.031, 0.090, 1.05
No. of reflections4639
No. of parameters529
No. of restraints4
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)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···AD—HH···AD···AD—H···A
O1—H1···O40.84 (1)2.14 (2)2.832 (2)140 (3)
O5—H5···O80.84 (1)2.12 (2)2.856 (2)145 (3)
O9—H9···O120.84 (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

First citationAli, Q., Ibad, F., Shah, M. R. & VanDerveer, D. (2008). Acta Cryst. E64, o1408.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationBarbour, L. J. (2001). J. Supramol. Chem. 1, 189–191.  CrossRef CAS Google Scholar
First citationBruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationWestrip, S. P. (2009). publCIF. In preparation.  Google Scholar

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