Buy article online - an online subscription or single-article purchase is required to access this article.
The title compound, C
9H
10O
3, also known as (
m-methoxyphenyl)acetic acid, has been found to crystallize in the monoclinic space group
P2
1/
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 O—H
O hydrogen bonds between the carboxyl groups, across a crystallographic centre of symmetry.
Supporting information
CCDC reference: 193761
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.002 Å
- R factor = 0.040
- wR factor = 0.117
- Data-to-parameter ratio = 11.5
checkCIF results
No syntax errors found
ADDSYM reports no extra symmetry
Data collection: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and CAMERON (Watkin et al., 1993); software used to prepare material for publication: PLATON (Spek, 1990).
(3-methoxyphenyl) acetic acid
top
Crystal data top
C9H10O3 | F(000) = 352 |
Mr = 166.17 | Dx = 1.317 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 3478 reflections |
a = 16.266 (3) Å | θ = 2.4–21.3° |
b = 5.1024 (11) Å | µ = 0.10 mm−1 |
c = 10.095 (2) Å | T = 293 K |
β = 90.73 (1)° | Prism, colourless |
V = 837.8 (3) Å3 | 0.40 × 0.35 × 0.20 mm |
Z = 4 | |
Data collection top
Bruker SMART CCD area-detector diffractometer | 1310 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.037 |
Graphite monochromator | θmax = 26.4°, θmin = 1.3° |
φ and ω scans | h = −20→20 |
6276 measured reflections | k = −6→6 |
1714 independent reflections | l = −12→12 |
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)] = 0.040 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.117 | H-atom parameters constrained |
S = 1.03 | w = 1/[σ2(Fo2) + (0.077P)2 + 0.0041P] where P = (Fo2 + 2Fc2)/3 |
1714 reflections | (Δ/σ)max = 0.003 |
149 parameters | Δρmax = 0.15 e Å−3 |
0 restraints | Δρmin = −0.16 e Å−3 |
Special details top
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes. |
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) top | 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) top | U11 | U22 | U33 | U12 | U13 | U23 |
O2 | 0.0590 (7) | 0.0726 (7) | 0.0871 (8) | 0.0166 (5) | −0.0215 (5) | −0.0202 (6) |
O3 | 0.0543 (7) | 0.0820 (8) | 0.0850 (8) | 0.0105 (5) | 0.0109 (5) | 0.0118 (6) |
O1 | 0.0562 (6) | 0.0795 (8) | 0.0780 (7) | 0.0159 (5) | −0.0183 (5) | −0.0306 (6) |
C1 | 0.0419 (7) | 0.0573 (8) | 0.0493 (7) | −0.0005 (6) | 0.0024 (5) | −0.0014 (6) |
C4 | 0.0533 (8) | 0.0482 (7) | 0.0444 (6) | −0.0007 (6) | −0.0058 (5) | 0.0013 (5) |
C5 | 0.0499 (8) | 0.0530 (8) | 0.0501 (7) | −0.0013 (6) | −0.0057 (6) | −0.0037 (6) |
C3 | 0.0475 (7) | 0.0537 (7) | 0.0465 (7) | −0.0063 (6) | −0.0071 (5) | −0.0094 (6) |
C6 | 0.0640 (10) | 0.0567 (8) | 0.0623 (8) | 0.0035 (7) | −0.0177 (7) | 0.0029 (7) |
C8 | 0.0626 (9) | 0.0702 (10) | 0.0517 (8) | −0.0193 (8) | −0.0005 (7) | 0.0006 (7) |
C2 | 0.0506 (8) | 0.0656 (9) | 0.0602 (8) | 0.0027 (6) | −0.0023 (6) | −0.0155 (7) |
C7 | 0.0833 (12) | 0.0611 (9) | 0.0580 (8) | −0.0110 (8) | −0.0152 (8) | 0.0138 (7) |
C9 | 0.0743 (11) | 0.0746 (11) | 0.0963 (13) | −0.0069 (9) | 0.0283 (10) | 0.0097 (10) |
Geometric parameters (Å, º) top
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) top
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2···O1i | 0.82 | 1.87 | 2.687 (2) | 173 |
Symmetry code: (i) −x, −y+1, −z+1. |
Subscribe to Acta Crystallographica Section E: Crystallographic Communications
The full text of this article is available to subscribers to the journal.
If you have already registered and are using a computer listed in your registration details, please email
support@iucr.org for assistance.