The title compound, C14H12O8, exists in the crystal structure in the enol form, as hydrogen-bonded dimers.
Supporting information
CCDC reference: 200762
Key indicators
- Single-crystal X-ray study
- T = 100 K
- Mean (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
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
C14H12O8 | F(000) = 320 |
Mr = 308.24 | Dx = 1.554 Mg m−3 |
Triclinic, P1 | Melting point: 130° c K |
a = 6.862 (1) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 7.335 (1) Å | Cell parameters from 180 reflections |
c = 13.323 (3) Å | θ = 10.3–21.1° |
α = 80.73 (1)° | µ = 0.13 mm−1 |
β = 85.30 (1)° | T = 100 K |
γ = 86.60 (1)° | Needle, colourless |
V = 658.9 (2) Å3 | 0.40 × 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 tube | Rint = 0.094 |
Graphite monochromator | θmax = 25.1°, θmin = 1.6° |
Detector resolution: 8 pixels mm-1 | h = −8→7 |
ω scans | k = −8→8 |
3856 measured reflections | l = −15→14 |
2328 independent reflections | |
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)] = 0.066 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.171 | H 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 parameters | Δρmax = 0.32 e Å−3 |
0 restraints | Δρmin = −0.34 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
O1 | 0.2366 (5) | 0.6253 (4) | 0.3429 (2) | 0.0158 (8) | |
O2 | 0.3986 (6) | 0.1485 (5) | 0.3613 (3) | 0.0220 (9) | |
H02 | 0.428 (10) | 0.141 (9) | 0.305 (5) | 0.05 (2)* | |
O3 | 0.2554 (5) | 0.6451 (4) | 0.1398 (2) | 0.0190 (9) | |
O4 | 0.3503 (5) | 0.3417 (4) | 0.1498 (3) | 0.0216 (9) | |
O5 | 0.0797 (5) | 0.8712 (4) | 0.6781 (2) | 0.0192 (9) | |
O6 | 0.1459 (5) | 0.6253 (4) | 0.7964 (3) | 0.0220 (9) | |
O7 | 0.1232 (5) | 1.0983 (4) | 0.8935 (3) | 0.0218 (9) | |
O8 | 0.3601 (5) | 0.9942 (4) | 0.7869 (3) | 0.0218 (9) | |
C2 | 0.2970 (7) | 0.4714 (6) | 0.2985 (4) | 0.0153 (12) | |
C3 | 0.3363 (7) | 0.3220 (6) | 0.3723 (4) | 0.0150 (11) | |
C4 | 0.3096 (7) | 0.2983 (7) | 0.5700 (4) | 0.0159 (12) | |
H4 | 0.3517 | 0.1725 | 0.5872 | 0.019* | |
C5 | 0.2575 (7) | 0.4064 (7) | 0.6440 (4) | 0.0194 (12) | |
H5 | 0.2638 | 0.3529 | 0.7134 | 0.023* | |
C6 | 0.1950 (7) | 0.5938 (6) | 0.6205 (4) | 0.0137 (11) | |
C7 | 0.1855 (7) | 0.6798 (7) | 0.5196 (4) | 0.0184 (12) | |
H7 | 0.1452 | 0.8062 | 0.5025 | 0.022* | |
C8 | 0.2386 (7) | 0.5692 (6) | 0.4457 (4) | 0.0147 (12) | |
C9 | 0.2982 (7) | 0.3806 (6) | 0.4690 (4) | 0.0160 (12) | |
C10 | 0.3058 (7) | 0.4778 (7) | 0.1903 (4) | 0.0182 (12) | |
C11 | 0.1409 (8) | 0.6935 (7) | 0.7080 (4) | 0.0191 (12) | |
C12 | 0.0154 (8) | 0.9703 (7) | 0.7599 (4) | 0.0191 (12) | |
H121 | −0.0730 | 0.8940 | 0.8097 | 0.025* | |
H122 | −0.0584 | 1.0851 | 0.7329 | 0.025* | |
C13 | 0.1879 (8) | 1.0177 (6) | 0.8122 (4) | 0.0185 (12) | |
C14 | 0.2700 (9) | 1.1704 (7) | 0.9467 (4) | 0.0322 (15) | |
H141 | 0.2086 | 1.2114 | 1.0086 | 0.070 (13)* | |
H142 | 0.3296 | 1.2751 | 0.9024 | 0.070 (13)* | |
H143 | 0.3709 | 1.0736 | 0.9650 | 0.070 (13)* | |
C15 | 0.2432 (8) | 0.6532 (7) | 0.0305 (4) | 0.0247 (14) | |
H151 | 0.1607 | 0.5558 | 0.0184 | 0.042 (10)* | |
H152 | 0.3745 | 0.6353 | −0.0020 | 0.042 (10)* | |
H153 | 0.1864 | 0.7739 | 0.0017 | 0.042 (10)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.014 (2) | 0.0165 (18) | 0.018 (2) | 0.0036 (15) | −0.0010 (15) | −0.0054 (16) |
O2 | 0.028 (2) | 0.017 (2) | 0.022 (2) | 0.0113 (16) | −0.0005 (18) | −0.0095 (18) |
O3 | 0.023 (2) | 0.0206 (19) | 0.012 (2) | 0.0030 (15) | −0.0024 (15) | −0.0007 (16) |
O4 | 0.023 (2) | 0.0191 (19) | 0.023 (2) | 0.0043 (16) | −0.0002 (16) | −0.0070 (17) |
O5 | 0.029 (2) | 0.0151 (18) | 0.0142 (19) | 0.0048 (15) | −0.0046 (16) | −0.0049 (15) |
O6 | 0.028 (2) | 0.0192 (19) | 0.017 (2) | 0.0043 (16) | −0.0042 (17) | −0.0009 (17) |
O7 | 0.022 (2) | 0.0253 (19) | 0.020 (2) | 0.0069 (16) | −0.0033 (16) | −0.0131 (17) |
O8 | 0.018 (2) | 0.0179 (19) | 0.030 (2) | 0.0021 (16) | −0.0016 (17) | −0.0070 (17) |
C2 | 0.018 (3) | 0.012 (3) | 0.018 (3) | −0.001 (2) | 0.001 (2) | −0.011 (2) |
C3 | 0.014 (3) | 0.016 (3) | 0.016 (3) | −0.001 (2) | −0.002 (2) | −0.003 (2) |
C4 | 0.012 (3) | 0.016 (3) | 0.020 (3) | 0.006 (2) | −0.007 (2) | −0.001 (2) |
C5 | 0.016 (3) | 0.022 (3) | 0.020 (3) | −0.006 (2) | −0.001 (2) | −0.003 (2) |
C6 | 0.011 (3) | 0.014 (2) | 0.017 (3) | 0.003 (2) | −0.001 (2) | −0.007 (2) |
C7 | 0.018 (3) | 0.016 (3) | 0.023 (3) | −0.003 (2) | −0.003 (2) | −0.007 (2) |
C8 | 0.012 (3) | 0.016 (3) | 0.015 (3) | −0.001 (2) | −0.003 (2) | 0.000 (2) |
C9 | 0.010 (3) | 0.016 (3) | 0.025 (3) | 0.005 (2) | −0.004 (2) | −0.010 (2) |
C10 | 0.017 (3) | 0.016 (3) | 0.020 (3) | 0.005 (2) | −0.003 (2) | −0.002 (2) |
C11 | 0.019 (3) | 0.014 (3) | 0.025 (3) | −0.003 (2) | −0.002 (2) | −0.003 (2) |
C12 | 0.024 (3) | 0.017 (3) | 0.017 (3) | 0.008 (2) | 0.000 (2) | −0.009 (2) |
C13 | 0.025 (4) | 0.010 (2) | 0.019 (3) | 0.006 (2) | −0.001 (2) | −0.002 (2) |
C14 | 0.035 (4) | 0.028 (3) | 0.039 (4) | 0.002 (3) | −0.015 (3) | −0.018 (3) |
C15 | 0.027 (4) | 0.027 (3) | 0.019 (3) | 0.009 (2) | −0.003 (2) | −0.003 (3) |
Geometric parameters (Å, º) top
O1—C8 | 1.367 (6) | O8—C13 | 1.212 (6) |
O1—C2 | 1.384 (5) | C2—C3 | 1.380 (6) |
O2—H02 | 0.77 (6) | C2—C10 | 1.431 (7) |
O2—C3 | 1.345 (6) | C3—C9 | 1.421 (7) |
O3—C10 | 1.342 (5) | C4—C5 | 1.374 (7) |
O3—C15 | 1.457 (6) | C4—C9 | 1.390 (7) |
O4—C10 | 1.221 (6) | C5—C6 | 1.409 (7) |
O5—C11 | 1.353 (6) | C6—C7 | 1.395 (6) |
O5—C12 | 1.432 (5) | C6—C11 | 1.485 (7) |
O6—C11 | 1.205 (6) | C7—C8 | 1.386 (7) |
O7—C13 | 1.348 (6) | C8—C9 | 1.411 (6) |
O7—C14 | 1.448 (6) | C12—C13 | 1.506 (7) |
| | | |
C8—O1—C2 | 105.8 (3) | O1—C8—C7 | 125.2 (4) |
H02—O2—C3 | 111 (5) | O1—C8—C9 | 111.5 (4) |
C10—O3—C15 | 115.0 (4) | C7—C8—C9 | 123.2 (4) |
C11—O5—C12 | 114.6 (4) | C4—C9—C8 | 120.0 (4) |
C13—O7—C14 | 116.8 (4) | C4—C9—C3 | 135.6 (4) |
C3—C2—O1 | 110.4 (4) | C8—C9—C3 | 104.4 (4) |
C3—C2—C10 | 128.2 (4) | O4—C10—O3 | 124.4 (5) |
O1—C2—C10 | 121.3 (4) | O4—C10—C2 | 122.3 (4) |
O2—C3—C2 | 129.2 (4) | O3—C10—C2 | 113.2 (4) |
O2—C3—C9 | 123.1 (4) | O6—C11—O5 | 122.8 (5) |
C2—C3—C9 | 107.8 (4) | O6—C11—C6 | 124.7 (4) |
C5—C4—C9 | 117.4 (4) | O5—C11—C6 | 112.5 (4) |
C4—C5—C6 | 122.4 (5) | O5—C12—C13 | 110.5 (4) |
C7—C6—C5 | 121.1 (4) | O8—C13—O7 | 123.0 (5) |
C7—C6—C11 | 122.2 (4) | O8—C13—C12 | 127.6 (5) |
C5—C6—C11 | 116.7 (4) | O7—C13—C12 | 109.4 (4) |
C8—C7—C6 | 115.9 (4) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H02···O8i | 0.77 (6) | 2.13 (6) | 2.768 (5) | 141 (6) |
Symmetry code: (i) −x+1, −y+1, −z+1. |