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The title compound, C14H12O8, exists in the crystal structure in the enol form, as hydrogen-bonded dimers.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802018524/cf6216sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536802018524/cf6216Isup2.hkl
Contains datablock I

CCDC reference: 200762

Key indicators

  • Single-crystal X-ray study
  • T = 100 K
  • Mean [sigma](C-C) = 0.007 Å
  • R factor = 0.066
  • wR factor = 0.171
  • Data-to-parameter ratio = 11.2

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry








Computing details top

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

Methoxycarbonylmethyl 2-methoxycarbonyl-3-Hydroxybenzo[b]furan-6-carboxylate top
Crystal data top
C14H12O8F(000) = 320
Mr = 308.24Dx = 1.554 Mg m3
Triclinic, P1Melting point: 130° c K
a = 6.862 (1) ÅMo Kα radiation, λ = 0.71073 Å
b = 7.335 (1) ÅCell parameters from 180 reflections
c = 13.323 (3) Åθ = 10.3–21.1°
α = 80.73 (1)°µ = 0.13 mm1
β = 85.30 (1)°T = 100 K
γ = 86.60 (1)°Needle, colourless
V = 658.9 (2) Å30.40 × 0.06 × 0.02 mm
Z = 2
Data collection top
SMART 1K CCD area-detector
diffractometer
1173 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.094
Graphite monochromatorθmax = 25.1°, θmin = 1.6°
Detector resolution: 8 pixels mm-1h = 87
ω scansk = 88
3856 measured reflectionsl = 1514
2328 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)] = 0.066Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.171H atoms treated by a mixture of independent and constrained refinement
S = 0.99 w = 1/[σ2(Fo2) + (0.0618P)2]
where P = (Fo2 + 2Fc2)/3
2328 reflections(Δ/σ)max < 0.001
207 parametersΔρmax = 0.32 e Å3
0 restraintsΔρmin = 0.34 e Å3
Special details top

Experimental. The data collection nominally covered more than a hemisphere of reciprocal space, by a combination of 4 sets of ω scans; each set at different φ and/or 2θ angles and each scan (20 sec exposure) covering 0.3° in ω. Crystal to detector distance 4.42 cm.

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.2366 (5)0.6253 (4)0.3429 (2)0.0158 (8)
O20.3986 (6)0.1485 (5)0.3613 (3)0.0220 (9)
H020.428 (10)0.141 (9)0.305 (5)0.05 (2)*
O30.2554 (5)0.6451 (4)0.1398 (2)0.0190 (9)
O40.3503 (5)0.3417 (4)0.1498 (3)0.0216 (9)
O50.0797 (5)0.8712 (4)0.6781 (2)0.0192 (9)
O60.1459 (5)0.6253 (4)0.7964 (3)0.0220 (9)
O70.1232 (5)1.0983 (4)0.8935 (3)0.0218 (9)
O80.3601 (5)0.9942 (4)0.7869 (3)0.0218 (9)
C20.2970 (7)0.4714 (6)0.2985 (4)0.0153 (12)
C30.3363 (7)0.3220 (6)0.3723 (4)0.0150 (11)
C40.3096 (7)0.2983 (7)0.5700 (4)0.0159 (12)
H40.35170.17250.58720.019*
C50.2575 (7)0.4064 (7)0.6440 (4)0.0194 (12)
H50.26380.35290.71340.023*
C60.1950 (7)0.5938 (6)0.6205 (4)0.0137 (11)
C70.1855 (7)0.6798 (7)0.5196 (4)0.0184 (12)
H70.14520.80620.50250.022*
C80.2386 (7)0.5692 (6)0.4457 (4)0.0147 (12)
C90.2982 (7)0.3806 (6)0.4690 (4)0.0160 (12)
C100.3058 (7)0.4778 (7)0.1903 (4)0.0182 (12)
C110.1409 (8)0.6935 (7)0.7080 (4)0.0191 (12)
C120.0154 (8)0.9703 (7)0.7599 (4)0.0191 (12)
H1210.07300.89400.80970.025*
H1220.05841.08510.73290.025*
C130.1879 (8)1.0177 (6)0.8122 (4)0.0185 (12)
C140.2700 (9)1.1704 (7)0.9467 (4)0.0322 (15)
H1410.20861.21141.00860.070 (13)*
H1420.32961.27510.90240.070 (13)*
H1430.37091.07360.96500.070 (13)*
C150.2432 (8)0.6532 (7)0.0305 (4)0.0247 (14)
H1510.16070.55580.01840.042 (10)*
H1520.37450.63530.00200.042 (10)*
H1530.18640.77390.00170.042 (10)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.014 (2)0.0165 (18)0.018 (2)0.0036 (15)0.0010 (15)0.0054 (16)
O20.028 (2)0.017 (2)0.022 (2)0.0113 (16)0.0005 (18)0.0095 (18)
O30.023 (2)0.0206 (19)0.012 (2)0.0030 (15)0.0024 (15)0.0007 (16)
O40.023 (2)0.0191 (19)0.023 (2)0.0043 (16)0.0002 (16)0.0070 (17)
O50.029 (2)0.0151 (18)0.0142 (19)0.0048 (15)0.0046 (16)0.0049 (15)
O60.028 (2)0.0192 (19)0.017 (2)0.0043 (16)0.0042 (17)0.0009 (17)
O70.022 (2)0.0253 (19)0.020 (2)0.0069 (16)0.0033 (16)0.0131 (17)
O80.018 (2)0.0179 (19)0.030 (2)0.0021 (16)0.0016 (17)0.0070 (17)
C20.018 (3)0.012 (3)0.018 (3)0.001 (2)0.001 (2)0.011 (2)
C30.014 (3)0.016 (3)0.016 (3)0.001 (2)0.002 (2)0.003 (2)
C40.012 (3)0.016 (3)0.020 (3)0.006 (2)0.007 (2)0.001 (2)
C50.016 (3)0.022 (3)0.020 (3)0.006 (2)0.001 (2)0.003 (2)
C60.011 (3)0.014 (2)0.017 (3)0.003 (2)0.001 (2)0.007 (2)
C70.018 (3)0.016 (3)0.023 (3)0.003 (2)0.003 (2)0.007 (2)
C80.012 (3)0.016 (3)0.015 (3)0.001 (2)0.003 (2)0.000 (2)
C90.010 (3)0.016 (3)0.025 (3)0.005 (2)0.004 (2)0.010 (2)
C100.017 (3)0.016 (3)0.020 (3)0.005 (2)0.003 (2)0.002 (2)
C110.019 (3)0.014 (3)0.025 (3)0.003 (2)0.002 (2)0.003 (2)
C120.024 (3)0.017 (3)0.017 (3)0.008 (2)0.000 (2)0.009 (2)
C130.025 (4)0.010 (2)0.019 (3)0.006 (2)0.001 (2)0.002 (2)
C140.035 (4)0.028 (3)0.039 (4)0.002 (3)0.015 (3)0.018 (3)
C150.027 (4)0.027 (3)0.019 (3)0.009 (2)0.003 (2)0.003 (3)
Geometric parameters (Å, º) top
O1—C81.367 (6)O8—C131.212 (6)
O1—C21.384 (5)C2—C31.380 (6)
O2—H020.77 (6)C2—C101.431 (7)
O2—C31.345 (6)C3—C91.421 (7)
O3—C101.342 (5)C4—C51.374 (7)
O3—C151.457 (6)C4—C91.390 (7)
O4—C101.221 (6)C5—C61.409 (7)
O5—C111.353 (6)C6—C71.395 (6)
O5—C121.432 (5)C6—C111.485 (7)
O6—C111.205 (6)C7—C81.386 (7)
O7—C131.348 (6)C8—C91.411 (6)
O7—C141.448 (6)C12—C131.506 (7)
C8—O1—C2105.8 (3)O1—C8—C7125.2 (4)
H02—O2—C3111 (5)O1—C8—C9111.5 (4)
C10—O3—C15115.0 (4)C7—C8—C9123.2 (4)
C11—O5—C12114.6 (4)C4—C9—C8120.0 (4)
C13—O7—C14116.8 (4)C4—C9—C3135.6 (4)
C3—C2—O1110.4 (4)C8—C9—C3104.4 (4)
C3—C2—C10128.2 (4)O4—C10—O3124.4 (5)
O1—C2—C10121.3 (4)O4—C10—C2122.3 (4)
O2—C3—C2129.2 (4)O3—C10—C2113.2 (4)
O2—C3—C9123.1 (4)O6—C11—O5122.8 (5)
C2—C3—C9107.8 (4)O6—C11—C6124.7 (4)
C5—C4—C9117.4 (4)O5—C11—C6112.5 (4)
C4—C5—C6122.4 (5)O5—C12—C13110.5 (4)
C7—C6—C5121.1 (4)O8—C13—O7123.0 (5)
C7—C6—C11122.2 (4)O8—C13—C12127.6 (5)
C5—C6—C11116.7 (4)O7—C13—C12109.4 (4)
C8—C7—C6115.9 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H02···O8i0.77 (6)2.13 (6)2.768 (5)141 (6)
Symmetry code: (i) x+1, y+1, z+1.
 

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