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The title compound, C8H6O4, consists of a cyclic diether fused to benzoic acid and crystallizes as a hydrogen-bonded carboxylic acid dimer.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806019933/hg2033sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806019933/hg2033Isup2.hkl
Contains datablock I

CCDC reference: 613708

Key indicators

  • Single-crystal X-ray study
  • T = 173 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.063
  • wR factor = 0.176
  • Data-to-parameter ratio = 10.0

checkCIF/PLATON results

No syntax errors found



Alert level B RINTA01_ALERT_3_B The value of Rint is greater than 0.15 Rint given 0.154 PLAT020_ALERT_3_B The value of Rint is greater than 0.10 ......... 0.15
Alert level C CELLV02_ALERT_1_C The supplied cell volume s.u. differs from that calculated from the cell parameter s.u.'s by > 2 Calculated cell volume su = 18.91 Cell volume su given = 16.00 PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ? PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 3.15
0 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: EXPOSE in IPDS Software (Stoe & Cie, 2000); cell refinement: CELL in IPDS Software; data reduction: INTEGRATE in IPDS Software; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97.

2,3-Methylenedioxybenzoic acid top
Crystal data top
C8H6O4F(000) = 344
Mr = 166.13Dx = 1.630 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 5689 reflections
a = 9.7327 (13) Åθ = 2.6–26.0°
b = 7.2600 (7) ŵ = 0.13 mm1
c = 12.394 (2) ÅT = 173 K
β = 129.395 (11)°Prism, colourless
V = 676.77 (16) Å30.50 × 0.40 × 0.20 mm
Z = 4
Data collection top
Stoe IPDS
diffractometer
957 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.154
Graphite monochromatorθmax = 25.9°, θmin = 2.7°
Detector resolution: 0.81 pixels mm-1h = 1111
φ scansk = 88
4940 measured reflectionsl = 1515
1302 independent reflections
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)] = 0.063Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.176H atoms treated by a mixture of independent and constrained refinement
S = 1.03 w = 1/[σ2(Fo2) + (0.1155P)2]
where P = (Fo2 + 2Fc2)/3
1302 reflections(Δ/σ)max < 0.001
130 parametersΔρmax = 0.33 e Å3
0 restraintsΔρmin = 0.54 e Å3
Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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
O10.3597 (2)0.5043 (2)0.03568 (18)0.0279 (6)
O20.4902 (2)0.2614 (2)0.02229 (19)0.0283 (6)
O30.0839 (2)0.2475 (2)0.22587 (19)0.0298 (6)
O40.1959 (3)0.4490 (2)0.1528 (2)0.0291 (6)
C10.3920 (3)0.3348 (3)0.0469 (2)0.0215 (7)
C20.3175 (3)0.2086 (3)0.0916 (2)0.0204 (7)
C30.3351 (3)0.0164 (3)0.0898 (2)0.0234 (7)
C40.2642 (3)0.1031 (4)0.1308 (3)0.0256 (7)
C50.1765 (3)0.0377 (3)0.1783 (2)0.0248 (8)
C60.1621 (3)0.1500 (3)0.1819 (2)0.0217 (7)
C70.2295 (3)0.2715 (3)0.1388 (2)0.0209 (7)
C80.1013 (4)0.4384 (3)0.2058 (3)0.0278 (8)
H20.529200.344100.000700.0430*
H30.395 (3)0.039 (4)0.057 (2)0.021 (6)*
H40.270 (3)0.222 (4)0.125 (3)0.031 (7)*
H50.121 (4)0.115 (4)0.205 (3)0.046 (8)*
H8A0.020 (4)0.482 (4)0.134 (3)0.036 (7)*
H8B0.164 (4)0.501 (5)0.290 (4)0.054 (9)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0409 (10)0.0120 (9)0.0451 (10)0.0030 (7)0.0340 (9)0.0040 (7)
O20.0418 (11)0.0181 (9)0.0474 (11)0.0005 (7)0.0388 (10)0.0003 (7)
O30.0474 (11)0.0163 (10)0.0516 (11)0.0012 (7)0.0436 (10)0.0017 (7)
O40.0485 (11)0.0090 (9)0.0560 (11)0.0018 (7)0.0455 (10)0.0006 (7)
C10.0307 (13)0.0152 (12)0.0295 (12)0.0008 (9)0.0242 (11)0.0007 (9)
C20.0282 (12)0.0103 (12)0.0289 (12)0.0009 (8)0.0210 (11)0.0006 (8)
C30.0322 (12)0.0146 (12)0.0296 (12)0.0018 (9)0.0226 (11)0.0012 (9)
C40.0367 (13)0.0102 (12)0.0348 (13)0.0005 (10)0.0250 (11)0.0003 (9)
C50.0333 (13)0.0132 (13)0.0335 (13)0.0029 (9)0.0239 (11)0.0010 (9)
C60.0290 (13)0.0147 (13)0.0268 (12)0.0003 (9)0.0203 (11)0.0006 (8)
C70.0298 (13)0.0115 (12)0.0314 (13)0.0001 (8)0.0242 (11)0.0010 (8)
C80.0453 (15)0.0132 (13)0.0454 (15)0.0037 (10)0.0385 (14)0.0037 (10)
Geometric parameters (Å, º) top
O1—C11.256 (3)C3—C41.390 (4)
O2—C11.289 (4)C4—C51.392 (5)
O3—C61.380 (4)C5—C61.374 (3)
O3—C81.437 (3)C6—C71.392 (4)
O4—C71.367 (3)C3—H30.98 (3)
O4—C81.433 (5)C4—H40.87 (3)
O2—H20.8400C5—H50.97 (4)
C1—C21.477 (4)C8—H8A0.98 (4)
C2—C71.386 (4)C8—H8B0.93 (4)
C2—C31.408 (3)
O1···O42.783 (4)C5···C5xii3.516 (3)
O1···O2i2.622 (3)C5···O2x3.338 (3)
O1···C1i3.375 (4)C5···C1x3.455 (4)
O2···O1i2.622 (3)C5···C6xii3.575 (3)
O2···C6ii3.363 (3)C6···O2v3.363 (3)
O2···C5iii3.338 (3)C6···C5xii3.575 (3)
O3···O42.324 (3)C6···C4xii3.455 (4)
O3···C8iv3.308 (4)C6···C1v3.555 (3)
O3···C1v3.168 (3)C8···O3ix3.308 (4)
O4···O32.324 (3)C1···H2i2.6400
O4···C4vi3.365 (3)C1···H8Avii3.10 (4)
O4···O12.783 (4)C3···H8Bii2.96 (4)
O1···H4vi2.68 (3)C8···H5ix3.02 (4)
O1···H8Avii2.56 (4)H2···O1i1.7900
O1···H2i1.7900H2···O2i2.8700
O2···H3viii2.49 (3)H2···C1i2.6400
O2···H2i2.8700H2···H2i2.3300
O2···H32.51 (3)H2···H3viii2.5800
O3···H8Aiv2.91 (4)H3···O22.51 (3)
O3···H8Biv2.91 (5)H3···O2viii2.49 (3)
O3···H5ix2.81 (4)H3···H2viii2.5800
O4···H4vi2.58 (3)H3···H8Bii2.58 (4)
O4···H8Avii2.85 (3)H4···O1xi2.68 (3)
C1···C4iii3.223 (4)H4···O4xi2.58 (3)
C1···C5iii3.455 (4)H5···O3iv2.81 (4)
C1···O1i3.375 (4)H5···C8iv3.02 (4)
C1···C6ii3.555 (3)H8A···O3ix2.91 (4)
C1···O3ii3.168 (3)H8A···O1vii2.56 (4)
C2···C4iii3.536 (4)H8A···O4vii2.85 (3)
C4···C1x3.223 (4)H8A···C1vii3.10 (4)
C4···C2x3.536 (4)H8B···O3ix2.91 (5)
C4···O4xi3.365 (3)H8B···C3v2.96 (4)
C4···C6xii3.455 (4)H8B···H3v2.58 (4)
C6—O3—C8105.7 (2)O4—C7—C2128.7 (3)
C7—O4—C8106.4 (2)C2—C7—C6121.4 (2)
C1—O2—H2109.00O4—C7—C6109.9 (3)
O1—C1—O2123.4 (3)O3—C8—O4108.2 (2)
O2—C1—C2116.5 (2)C2—C3—H3121.5 (17)
O1—C1—C2120.1 (3)C4—C3—H3117.2 (17)
C1—C2—C7122.4 (2)C3—C4—H4121 (2)
C3—C2—C7116.6 (3)C5—C4—H4118 (2)
C1—C2—C3121.0 (3)C4—C5—H5125 (2)
C2—C3—C4121.3 (3)C6—C5—H5118 (2)
C3—C4—C5121.4 (3)O3—C8—H8A105.3 (19)
C4—C5—C6117.0 (3)O3—C8—H8B110 (2)
O3—C6—C7109.8 (2)O4—C8—H8A109 (2)
C5—C6—C7122.2 (3)O4—C8—H8B110 (3)
O3—C6—C5128.0 (3)H8A—C8—H8B115 (3)
C8—O3—C6—C5178.8 (2)C1—C2—C3—C4179.5 (2)
C8—O3—C6—C71.2 (3)C3—C2—C7—O4179.2 (2)
C6—O3—C8—O41.6 (3)C1—C2—C7—O40.0 (4)
C8—O4—C7—C2180.0 (2)C1—C2—C7—C6179.3 (2)
C8—O4—C7—C60.6 (3)C2—C3—C4—C51.5 (4)
C7—O4—C8—O31.4 (3)C3—C4—C5—C60.4 (4)
O2—C1—C2—C37.8 (3)C4—C5—C6—C70.8 (3)
O1—C1—C2—C3172.8 (2)C4—C5—C6—O3179.2 (2)
O1—C1—C2—C78.1 (3)C5—C6—C7—C21.0 (3)
O2—C1—C2—C7171.4 (2)O3—C6—C7—O40.4 (3)
C3—C2—C7—C60.1 (3)O3—C6—C7—C2179.0 (2)
C7—C2—C3—C41.3 (3)C5—C6—C7—O4179.7 (2)
Symmetry codes: (i) x+1, y+1, z; (ii) x, y+1/2, z1/2; (iii) x+1, y+1/2, z+1/2; (iv) x, y1/2, z+1/2; (v) x, y+1/2, z+1/2; (vi) x, y+1, z; (vii) x, y+1, z; (viii) x+1, y, z; (ix) x, y+1/2, z+1/2; (x) x+1, y1/2, z+1/2; (xi) x, y1, z; (xii) x, y, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2···O1i0.841.792.622 (3)171
C3—H3···O2viii0.98 (3)2.49 (3)3.448 (4)164 (2)
C4—H4···O4xi0.87 (3)2.58 (3)3.365 (3)150 (3)
C8—H8A···O1vii0.98 (4)2.56 (4)3.495 (4)161 (3)
Symmetry codes: (i) x+1, y+1, z; (vii) x, y+1, z; (viii) x+1, y, z; (xi) x, y1, z.
 

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