Acta Cryst.(2002). E58, o889±o890 DOI: 10.1107/S1600536802012102 Choudhury and Row C9H10O3
o889
organic papers
Acta Crystallographica Section E Structure Reports Online
ISSN 1600-5368
(3-Methoxyphenyl)acetic acid
A. R Choudhury and T. N. Guru Row*
Solid State and Structural Chemistry Unit, Indian Institute of Science, Bangalore 560 012, Karnataka, India
Correspondence e-mail: ssctng@sscu.iisc.ernet.in
Key indicators Single-crystal X-ray study
T= 293 K
Mean(C±C) = 0.002 AÊ
Rfactor = 0.040
wRfactor = 0.117
Data-to-parameter ratio = 11.5
For details of how these key indicators were automatically derived from the article, see http://journals.iucr.org/e.
#2002 International Union of Crystallography Printed in Great Britain ± all rights reserved
The title compound, C9H10O3, also known as (m
-methoxy-phenyl)acetic acid, has been found to crystallize in the monoclinic space groupP21/c at room temperature. It is the
starting material for the synthesis of a large number of
1,2,3,4-tetrahydroisoquinoline compounds [Nagarajan et al. (1985).
Indian J. Chem. Sect. B, 24, 83±97]. The compound forms
dimers in the crystalline state, with OÐH O hydrogen
bonds between the carboxyl groups, across a crystallographic centre of symmetry.
Experimental
The 98% pure compound was bought from Sigma Aldrich. Single crystals were grown from a mixture of ethyl acetate and hexane at room temperature, by slow evaporation. The compound crystallizes as prisms.
Crystal data
C9H10O3
Mr= 166.17 Monoclinic,P21=c
a= 16.266 (3) AÊ b= 5.1024 (11) AÊ c= 10.095 (2) AÊ
= 90.73 (1)
V= 837.8 (3) AÊ3
Z= 4
Dx= 1.317 Mg mÿ3 MoKradiation Cell parameters from 3478
re¯ections
= 2.4±21.3
= 0.10 mmÿ1
T= 293 (2) K Prism, colourless 0.400.350.20 mm
Received 5 July 2002 Accepted 9 July 2002 Online 19 July 2002
Figure 1
Data collection
Bruker SMART CCD area-detector diffractometer
'and!scans
Absorption correction: none 6276 measured re¯ections 1714 independent re¯ections
1310 re¯ections withI> 2(I) Rint= 0.037
max= 26.4
h=ÿ20!20 k=ÿ6!6 l=ÿ12!12
Re®nement
Re®nement onF2
R[F2> 2(F2)] = 0.040
wR(F2) = 0.117
S= 1.03 1714 re¯ections 149 parameters
H-atom parameters constrained
w= 1/[2(F
o2) + (0.077P)2 + 0.0041P]
whereP= (Fo2+ 2Fc2)/3 (/)max= 0.003
max= 0.15 e AÊÿ3
min=ÿ0.16 e AÊÿ3
Table 1
Hydrogen-bonding geometry (AÊ,).
DÐH A DÐH H A D A DÐH A
O2ÐH2 O1i 0.82 1.87 2.687 (2) 173
Symmetry code: (i)ÿx;1ÿy;1ÿz.
Data collection:SMART(Bruker, 1998); cell re®nement:SMART; data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to re®ne structure: SHELXL97 (Sheldrick, 1997); molecular graphics:
ORTEP-3 for Windows (Farrugia, 1997) andCAMERON(Watkinet al., 1993); software used to prepare material for publication:
PLATON(Spek, 1990).
The authors thank the Department of Science and Tech-nology, India, for the data collection on the CCD facility set up under the IRFA-DST programme.
References
Bruker (1998).SMARTandSAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Farrugia, L. J. (1997).J. Appl. Cryst.30, 565.
Nagarajan, K., Talwalker, P. K., Kulkarni, C. L., Shah, R. K., Shenoy, S. J. & Pravu, S. S. (1985).Indian J. Chem. Sect. B,24, 83±97.
Sheldrick, G. M. (1997). SHELXL97 and SHELXS97. University of GoÈttingen, Germany.
Spek, A. L. (1990).Acta Cryst.A46, C-34.
Watkin, D. J., Pearce, L. & Prout, C. K. (1993). CAMERON. Chemical Crystallography Laboratory, University of Oxford, England.
Figure 2
supporting information
sup-1 Acta Cryst. (2002). E58, o889–o890
supporting information
Acta Cryst. (2002). E58, o889–o890 [https://doi.org/10.1107/S1600536802012102]
(3-Methoxyphenyl)acetic acid
A. R Choudhury and T. N. Guru Row
(3-methoxyphenyl) acetic acid
Crystal data
C9H10O3 Mr = 166.17
Monoclinic, P21/c
Hall symbol: -P 2ybc a = 16.266 (3) Å b = 5.1024 (11) Å c = 10.095 (2) Å β = 90.73 (1)° V = 837.8 (3) Å3 Z = 4
F(000) = 352 Dx = 1.317 Mg m−3
Mo Kα radiation, λ = 0.71073 Å Cell parameters from 3478 reflections θ = 2.4–21.3°
µ = 0.10 mm−1 T = 293 K Prism, colourless 0.40 × 0.35 × 0.20 mm
Data collection
Bruker SMART CCD area-detector diffractometer
Radiation source: fine-focus sealed tube Graphite monochromator
φ and ω scans
6276 measured reflections 1714 independent reflections
1310 reflections with I > 2σ(I) Rint = 0.037
θmax = 26.4°, θmin = 1.3° h = −20→20
k = −6→6 l = −12→12
Refinement
Refinement on F2
Least-squares matrix: full R[F2 > 2σ(F2)] = 0.040 wR(F2) = 0.117 S = 1.03 1714 reflections 149 parameters 0 restraints
Primary atom site location: structure-invariant direct methods
Secondary atom site location: difference Fourier map
Hydrogen site location: inferred from neighbouring sites
H-atom parameters constrained w = 1/[σ2(F
o2) + (0.077P)2 + 0.0041P]
where P = (Fo2 + 2Fc2)/3
(Δ/σ)max = 0.003
Δρmax = 0.15 e Å−3
Δρmin = −0.16 e Å−3
Special details
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)
x y z Uiso*/Ueq
O2 0.00838 (6) 0.7832 (2) 0.60937 (12) 0.0731 (4)
H2 −0.0185 0.7149 0.5493 0.110*
O3 0.41770 (7) 0.5419 (2) 0.63480 (11) 0.0737 (4) O1 0.08963 (6) 0.4467 (2) 0.57274 (11) 0.0714 (4) C1 0.07511 (8) 0.6489 (3) 0.63060 (13) 0.0495 (3) C4 0.27706 (8) 0.6621 (3) 0.68455 (12) 0.0487 (3)
H4 0.2764 0.7924 0.6201 0.058*
C5 0.34717 (8) 0.5141 (3) 0.70481 (13) 0.0511 (4) C3 0.20771 (8) 0.6175 (3) 0.75966 (12) 0.0493 (3) C6 0.34836 (9) 0.3195 (3) 0.80052 (15) 0.0612 (4)
H6 0.3950 0.2170 0.8134 0.073*
C8 0.21015 (10) 0.4272 (3) 0.85640 (14) 0.0615 (4)
H8 0.1644 0.3982 0.9086 0.074*
C2 0.13036 (9) 0.7699 (3) 0.73258 (15) 0.0588 (4)
H2A 0.1004 0.7872 0.8145 0.071*
H2B 0.1451 0.9447 0.7035 0.071*
C7 0.28013 (11) 0.2797 (3) 0.87604 (15) 0.0676 (5)
H7 0.2811 0.1513 0.9414 0.081*
C9 0.42115 (11) 0.7507 (3) 0.5427 (2) 0.0815 (5)
H9A 0.3779 0.7310 0.4780 0.122*
H9B 0.4733 0.7485 0.4993 0.122*
H9C 0.4146 0.9143 0.5884 0.122*
Atomic displacement parameters (Å2)
U11 U22 U33 U12 U13 U23
supporting information
sup-3 Acta Cryst. (2002). E58, o889–o890
Geometric parameters (Å, º)
O2—C1 1.2991 (16) C3—C2 1.5011 (19)
O2—H2 0.820 C6—C7 1.370 (2)
O3—C5 1.3626 (17) C6—H6 0.930
O3—C9 1.415 (2) C8—C7 1.377 (2)
O1—C1 1.2104 (16) C8—H8 0.930
C1—C2 1.4917 (19) C2—H2A 0.970
C4—C5 1.3809 (19) C2—H2B 0.970
C4—C3 1.3860 (19) C7—H7 0.930
C4—H4 0.930 C9—H9A 0.960
C5—C6 1.385 (2) C9—H9B 0.960
C3—C8 1.377 (2) C9—H9C 0.960
C1—O2—H2 109.5 C7—C8—H8 119.9
C5—O3—C9 117.39 (12) C3—C8—H8 119.9
O1—C1—O2 122.53 (12) C1—C2—C3 114.05 (11)
O1—C1—C2 124.49 (12) C1—C2—H2A 108.7
O2—C1—C2 112.98 (12) C3—C2—H2A 108.7
C5—C4—C3 120.38 (12) C1—C2—H2B 108.7
C5—C4—H4 119.8 C3—C2—H2B 108.7
C3—C4—H4 119.8 H2A—C2—H2B 107.6
O3—C5—C4 124.42 (12) C6—C7—C8 120.86 (14)
O3—C5—C6 115.61 (13) C6—C7—H7 119.6
C4—C5—C6 119.96 (13) C8—C7—H7 119.6
C8—C3—C4 119.16 (13) O3—C9—H9A 109.5
C8—C3—C2 120.72 (13) O3—C9—H9B 109.5
C4—C3—C2 120.10 (12) H9A—C9—H9B 109.5
C7—C6—C5 119.37 (14) O3—C9—H9C 109.5
C7—C6—H6 120.3 H9A—C9—H9C 109.5
C5—C6—H6 120.3 H9B—C9—H9C 109.5
C7—C8—C3 120.25 (14)
Hydrogen-bond geometry (Å, º)
D—H···A D—H H···A D···A D—H···A
O2—H2···O1i 0.82 1.87 2.687 (2) 173
