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The title compound, C11H12O6, is a key inter­mediate for the synthesis of naturally occurring biologically active isocoumarin derivatives. In the crystal packing, mol­ecules are linked into a two-dimensional network structure via inter­molecular C—H...O hydrogen bonds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806003345/rz6167sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806003345/rz6167Isup2.hkl
Contains datablock I

CCDC reference: 601234

Key indicators

  • Single-crystal X-ray study
  • T = 292 K
  • Mean [sigma](C-C)= 0.002 Å
  • R factor = 0.044
  • wR factor = 0.125
  • Data-to-parameter ratio = 14.7

checkCIF/PLATON results

No syntax errors found


No errors found in this datablock

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1999); software used to prepare material for publication: SHELXTL.

2-(Carboxymethyl)-4,6-dimethoxybenzoic acid top
Crystal data top
C11H12O6Z = 2
Mr = 240.21F(000) = 252
Triclinic, P1Dx = 1.442 Mg m3
Hall symbol: -P 1Melting point: 170 K
a = 7.2886 (10) ÅMo Kα radiation, λ = 0.71073 Å
b = 7.9631 (11) ÅCell parameters from 2688 reflections
c = 10.2758 (14) Åθ = 2.7–28.2°
α = 105.937 (2)°µ = 0.12 mm1
β = 103.444 (2)°T = 292 K
γ = 93.211 (2)°Block, light yellow
V = 553.17 (13) Å30.24 × 0.20 × 0.20 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer
2380 independent reflections
Radiation source: fine-focus sealed tube2074 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.048
φ and ω scansθmax = 27.0°, θmin = 2.1°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 99
Tmin = 0.966, Tmax = 0.977k = 1010
4782 measured reflectionsl = 1213
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)] = 0.044Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.126H atoms treated by a mixture of independent and constrained refinement
S = 1.08 w = 1/[σ2(Fo2) + (0.0658P)2 + 0.0652P]
where P = (Fo2 + 2Fc2)/3
2380 reflections(Δ/σ)max < 0.001
162 parametersΔρmax = 0.24 e Å3
2 restraintsΔρmin = 0.19 e Å3
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
xyzUiso*/Ueq
C10.28940 (18)0.75801 (16)0.68898 (14)0.0361 (3)
C20.10780 (19)0.81130 (16)0.68927 (13)0.0364 (3)
C30.02643 (18)0.77948 (17)0.55930 (14)0.0368 (3)
C40.01674 (18)0.69458 (18)0.43471 (14)0.0382 (3)
H40.07340.67360.34960.046*
C50.19461 (19)0.64154 (17)0.43824 (14)0.0375 (3)
C60.33021 (19)0.67400 (17)0.56503 (14)0.0383 (3)
H60.44980.63850.56610.046*
C70.4516 (2)0.80226 (18)0.82010 (15)0.0422 (3)
H7A0.57050.81070.79380.051*
H7B0.44200.91710.88030.051*
C80.45863 (19)0.67338 (17)0.90187 (14)0.0395 (3)
C90.0631 (2)0.89595 (17)0.82393 (14)0.0400 (3)
C100.3249 (2)0.8280 (2)0.43127 (17)0.0485 (4)
H10A0.26020.89180.38470.073*
H10B0.43480.88220.44830.073*
H10C0.36380.70840.37330.073*
C110.1312 (3)0.5536 (3)0.18904 (16)0.0577 (4)
H11A0.01210.48290.17220.087*
H11B0.19260.50360.11680.087*
H11C0.10880.67110.18870.087*
O10.57813 (17)0.73299 (14)1.02706 (11)0.0586 (3)
H10.591 (3)0.649 (2)1.064 (2)0.088*
O20.37228 (14)0.52591 (12)0.85679 (10)0.0478 (3)
O30.13985 (17)0.86083 (14)0.93203 (11)0.0546 (3)
O40.05790 (19)1.00945 (16)0.82345 (12)0.0623 (4)
H4A0.071 (3)1.045 (3)0.9062 (13)0.093*
O50.20053 (14)0.83024 (15)0.56072 (11)0.0512 (3)
O60.24990 (14)0.55808 (15)0.32166 (10)0.0505 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0413 (7)0.0335 (6)0.0330 (7)0.0039 (5)0.0072 (5)0.0113 (5)
C20.0448 (7)0.0334 (6)0.0310 (7)0.0060 (5)0.0112 (6)0.0082 (5)
C30.0376 (7)0.0392 (6)0.0344 (7)0.0079 (5)0.0113 (5)0.0099 (5)
C40.0381 (7)0.0452 (7)0.0292 (6)0.0062 (5)0.0066 (5)0.0094 (5)
C50.0410 (7)0.0388 (6)0.0331 (7)0.0064 (5)0.0132 (6)0.0081 (5)
C60.0358 (6)0.0422 (7)0.0380 (7)0.0094 (5)0.0102 (5)0.0120 (6)
C70.0437 (7)0.0420 (7)0.0356 (7)0.0031 (6)0.0035 (6)0.0089 (6)
C80.0406 (7)0.0405 (7)0.0319 (7)0.0103 (5)0.0037 (5)0.0056 (5)
C90.0512 (8)0.0359 (6)0.0325 (7)0.0083 (6)0.0119 (6)0.0080 (5)
C100.0413 (7)0.0565 (9)0.0503 (9)0.0160 (6)0.0114 (6)0.0186 (7)
C110.0642 (10)0.0761 (11)0.0323 (8)0.0200 (8)0.0165 (7)0.0096 (7)
O10.0744 (8)0.0453 (6)0.0393 (6)0.0015 (5)0.0142 (5)0.0113 (5)
O20.0556 (6)0.0400 (5)0.0383 (5)0.0034 (4)0.0041 (4)0.0105 (4)
O30.0777 (8)0.0583 (6)0.0332 (5)0.0286 (6)0.0187 (5)0.0148 (5)
O40.0877 (9)0.0680 (8)0.0366 (6)0.0429 (7)0.0223 (6)0.0127 (5)
O50.0411 (5)0.0721 (7)0.0379 (6)0.0195 (5)0.0121 (4)0.0082 (5)
O60.0472 (6)0.0686 (7)0.0333 (5)0.0188 (5)0.0145 (4)0.0057 (5)
Geometric parameters (Å, º) top
C1—C61.3743 (19)C8—O21.2136 (17)
C1—C21.4128 (18)C8—O11.3177 (16)
C1—C71.5131 (18)C9—O31.2346 (17)
C2—C31.4085 (18)C9—O41.2979 (17)
C2—C91.4822 (18)C10—O51.4197 (17)
C3—O51.3552 (15)C10—H10A0.9600
C3—C41.3896 (18)C10—H10B0.9600
C4—C51.3814 (18)C10—H10C0.9600
C4—H40.9300C11—O61.4243 (18)
C5—O61.3625 (16)C11—H11A0.9600
C5—C61.3888 (19)C11—H11B0.9600
C6—H60.9300C11—H11C0.9600
C7—C81.490 (2)O1—H10.853 (10)
C7—H7A0.9700O4—H4A0.850 (10)
C7—H7B0.9700
C6—C1—C2120.35 (12)H7A—C7—H7B107.5
C6—C1—C7116.69 (12)O2—C8—O1122.97 (13)
C2—C1—C7122.77 (12)O2—C8—C7124.33 (12)
C3—C2—C1117.97 (12)O1—C8—C7112.59 (12)
C3—C2—C9122.14 (12)O3—C9—O4121.67 (12)
C1—C2—C9119.88 (12)O3—C9—C2121.09 (12)
O5—C3—C4121.37 (12)O4—C9—C2117.24 (12)
O5—C3—C2117.53 (11)O5—C10—H10A109.5
C4—C3—C2121.07 (12)O5—C10—H10B109.5
C5—C4—C3119.49 (12)H10A—C10—H10B109.5
C5—C4—H4120.3O5—C10—H10C109.5
C3—C4—H4120.3H10A—C10—H10C109.5
O6—C5—C4123.65 (12)H10B—C10—H10C109.5
O6—C5—C6115.93 (11)O6—C11—H11A109.5
C4—C5—C6120.42 (12)O6—C11—H11B109.5
C1—C6—C5120.66 (12)H11A—C11—H11B109.5
C1—C6—H6119.7O6—C11—H11C109.5
C5—C6—H6119.7H11A—C11—H11C109.5
C8—C7—C1114.89 (11)H11B—C11—H11C109.5
C8—C7—H7A108.5C8—O1—H1108.8 (16)
C1—C7—H7A108.5C9—O4—H4A107.1 (16)
C8—C7—H7B108.5C3—O5—C10117.93 (11)
C1—C7—H7B108.5C5—O6—C11117.71 (11)
C6—C1—C2—C31.54 (19)O6—C5—C6—C1179.77 (11)
C7—C1—C2—C3173.28 (12)C4—C5—C6—C10.5 (2)
C6—C1—C2—C9177.77 (12)C6—C1—C7—C897.26 (15)
C7—C1—C2—C97.40 (19)C2—C1—C7—C887.74 (15)
C1—C2—C3—O5179.67 (11)C1—C7—C8—O215.7 (2)
C9—C2—C3—O50.37 (19)C1—C7—C8—O1167.93 (11)
C1—C2—C3—C41.48 (19)C3—C2—C9—O3149.68 (14)
C9—C2—C3—C4177.82 (12)C1—C2—C9—O329.6 (2)
O5—C3—C4—C5178.56 (12)C3—C2—C9—O431.08 (19)
C2—C3—C4—C50.4 (2)C1—C2—C9—O4149.64 (13)
C3—C4—C5—O6179.78 (12)C4—C3—O5—C1012.8 (2)
C3—C4—C5—C60.6 (2)C2—C3—O5—C10168.99 (12)
C2—C1—C6—C50.6 (2)C4—C5—O6—C1111.6 (2)
C7—C1—C6—C5174.55 (11)C6—C5—O6—C11167.67 (13)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C7—H7B···O30.972.432.7829 (19)101
C10—H10C···O2i0.962.563.4144 (19)148
O4—H4A···O3ii0.85 (1)1.82 (1)2.6606 (14)169 (2)
O1—H1···O2iii0.85 (1)1.80 (1)2.6532 (14)178 (2)
Symmetry codes: (i) x, y+1, z+1; (ii) x, y+2, z+2; (iii) x+1, y+1, z+2.
 

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