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The title compound, C12H12O5, exists as two independent, relatively planar mol­ecules in the asymmetric unit; these differ in the orientation of the ester group.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803016490/bt6315sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803016490/bt6315Isup2.hkl
Contains datablock I

CCDC reference: 221721

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.006 Å
  • R factor = 0.051
  • wR factor = 0.123
  • Data-to-parameter ratio = 7.0

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

General Notes

REFLT_03 From the CIF: _diffrn_reflns_theta_max 25.00 From the CIF: _reflns_number_total 2154 Count of symmetry unique reflns 2155 Completeness (_total/calc) 99.95% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 0 Fraction of Friedel pairs measured 0.000 Are heavy atom types Z>Si present no Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SMART; data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.

Methyl 8-hydroxy-(S)-3-methyl-1-oxo-isochromane-5-carboxylate top
Crystal data top
C12H12O5F(000) = 496
Mr = 236.22Dx = 1.398 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
a = 10.9633 (7) ÅCell parameters from 2648 reflections
b = 7.1890 (5) Åθ = 2.5–23.7°
c = 14.425 (1) ŵ = 0.11 mm1
β = 99.088 (1)°T = 298 K
V = 1122.7 (1) Å3Needle, colorless
Z = 40.53 × 0.19 × 0.11 mm
Data collection top
Bruker AXS area-detector
diffractometer
1700 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.039
Graphite monochromatorθmax = 25.0°, θmin = 1.4°
φ and ω scansh = 1213
8222 measured reflectionsk = 88
2154 independent reflectionsl = 1617
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.051H-atom parameters constrained
wR(F2) = 0.123 w = 1/[σ2(Fo2) + (0.069P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max = 0.001
2154 reflectionsΔρmax = 0.18 e Å3
309 parametersΔρmin = 0.18 e Å3
1 restraintAbsolute structure: Calculation of Flack parameter suppressed by MERG 4.
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O1a0.1124 (3)0.4999 (5)0.6625 (2)0.077 (1)
O2a0.1380 (3)0.5214 (7)0.8156 (2)0.101 (1)
O3a0.6899 (3)0.6521 (8)0.7795 (2)0.098 (1)
O4a0.6744 (3)0.6316 (5)0.5996 (2)0.071 (1)
O5a0.4977 (3)0.6341 (5)0.5074 (2)0.056 (1)
C1a0.0178 (4)0.4653 (9)0.6593 (4)0.088 (2)
C2a0.1806 (4)0.5259 (6)0.7453 (3)0.060 (1)
C3a0.3133 (4)0.5603 (6)0.7431 (3)0.050 (1)
C4a0.3863 (4)0.5739 (7)0.8306 (3)0.066 (1)
C5a0.5099 (4)0.6048 (9)0.8418 (3)0.075 (2)
C6a0.5681 (4)0.6260 (8)0.7638 (3)0.063 (1)
C7a0.4970 (3)0.6143 (6)0.6743 (3)0.050 (1)
C8a0.3687 (3)0.5825 (5)0.6631 (2)0.044 (1)
C9a0.3045 (3)0.5693 (7)0.5634 (2)0.051 (1)
C10a0.3670 (3)0.6817 (6)0.4978 (3)0.047 (1)
C11a0.3147 (4)0.6541 (8)0.3962 (3)0.067 (1)
C12a0.5621 (4)0.6278 (6)0.5927 (3)0.052 (1)
O1b0.4391 (3)0.6033 (6)0.1957 (2)0.084 (1)
O2b0.5196 (3)0.5765 (8)0.0678 (2)0.104 (2)
O3b0.9688 (3)0.4868 (6)0.4095 (2)0.079 (1)
O4b1.0793 (3)0.4120 (6)0.2699 (2)0.084 (1)
O5b0.9985 (3)0.4847 (5)0.1266 (2)0.073 (1)
C1b0.3190 (4)0.618 (1)0.1384 (4)0.113 (3)
C2b0.5343 (4)0.5818 (7)0.1513 (3)0.060 (1)
C3b0.6521 (3)0.5661 (6)0.2157 (3)0.047 (1)
C4b0.6543 (4)0.5808 (7)0.3119 (3)0.055 (1)
C5b0.7589 (4)0.5598 (6)0.3755 (3)0.054 (1)
C6b0.8683 (4)0.5180 (6)0.3445 (3)0.055 (1)
C7b0.8713 (4)0.5077 (6)0.2479 (3)0.050 (1)
C8b0.7634 (3)0.5321 (6)0.1834 (3)0.049 (1)
C9b0.7770 (4)0.5170 (8)0.0819 (3)0.064 (1)
C10b0.9012 (4)0.5847 (8)0.0650 (3)0.064 (1)
C11b0.9244 (4)0.5530 (9)0.0334 (3)0.082 (2)
C12b0.9888 (4)0.4651 (7)0.2161 (3)0.060 (1)
H3a0.71560.65860.72920.118*
H1aa0.05620.44850.59530.131*
H1ab0.05490.56930.68600.131*
H1ac0.02890.35500.69460.131*
H4a0.34890.56140.88390.079*
H5a0.55560.61160.90180.090*
H9aa0.30200.44020.54380.062*
H9ab0.22000.61210.56000.062*
H10a0.35990.81350.51330.056*
H11a0.35920.73000.35810.101*
H11b0.22910.68910.38570.101*
H11c0.32230.52570.37980.101*
H3b1.02700.45660.38330.095*
H1ba0.25710.63310.17800.169*
H1bb0.30230.50630.10180.169*
H1bc0.31770.72270.09720.169*
H4b0.58080.60610.33380.066*
H5b0.75670.57360.43930.065*
H9ba0.71290.58970.04440.076*
H9bb0.76650.38820.06220.076*
H10b0.90830.71790.07920.077*
H11d1.00370.60290.04030.123*
H11e0.86140.61380.07660.123*
H11f0.92310.42200.04630.123*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O1a0.053 (2)0.103 (3)0.078 (2)0.013 (2)0.026 (2)0.001 (2)
O2a0.088 (2)0.155 (4)0.072 (2)0.011 (3)0.049 (2)0.007 (3)
O3a0.052 (2)0.175 (4)0.066 (2)0.000 (2)0.008 (2)0.007 (3)
O4a0.047 (2)0.105 (3)0.066 (2)0.005 (2)0.020 (1)0.006 (2)
O5a0.051 (2)0.076 (2)0.043 (2)0.002 (2)0.017 (1)0.004 (2)
C1a0.052 (3)0.109 (5)0.106 (4)0.013 (3)0.028 (3)0.000 (4)
C2a0.070 (3)0.055 (3)0.060 (3)0.001 (2)0.032 (2)0.009 (2)
C3a0.059 (2)0.046 (2)0.048 (2)0.006 (2)0.021 (2)0.003 (2)
C4a0.084 (3)0.073 (3)0.047 (3)0.007 (3)0.031 (2)0.011 (2)
C5a0.069 (3)0.112 (4)0.041 (2)0.008 (3)0.000 (2)0.005 (3)
C6a0.062 (3)0.085 (4)0.043 (3)0.012 (3)0.010 (2)0.001 (2)
C7a0.051 (2)0.053 (3)0.047 (2)0.008 (2)0.015 (2)0.001 (2)
C8a0.051 (2)0.038 (2)0.046 (2)0.005 (2)0.019 (2)0.005 (2)
C9a0.052 (2)0.060 (3)0.044 (2)0.002 (2)0.014 (2)0.007 (2)
C10a0.048 (2)0.048 (2)0.047 (2)0.006 (2)0.015 (2)0.000 (2)
C11a0.069 (3)0.089 (4)0.046 (3)0.015 (3)0.014 (2)0.003 (2)
C12a0.051 (2)0.054 (3)0.052 (3)0.002 (2)0.015 (2)0.004 (2)
O1b0.054 (2)0.142 (3)0.060 (2)0.018 (2)0.023 (2)0.010 (2)
O2b0.065 (2)0.202 (5)0.045 (2)0.018 (3)0.013 (2)0.006 (3)
O3b0.069 (2)0.114 (3)0.052 (2)0.004 (2)0.001 (2)0.002 (2)
O4b0.049 (2)0.132 (3)0.067 (2)0.001 (2)0.002 (2)0.009 (2)
O5b0.054 (2)0.108 (3)0.060 (2)0.006 (2)0.022 (2)0.007 (2)
C1b0.054 (3)0.205 (8)0.079 (4)0.022 (4)0.012 (2)0.020 (5)
C2b0.063 (3)0.070 (3)0.053 (3)0.002 (2)0.023 (2)0.007 (2)
C3b0.055 (2)0.045 (2)0.045 (2)0.001 (2)0.021 (2)0.004 (2)
C4b0.060 (3)0.058 (3)0.053 (2)0.011 (2)0.024 (2)0.000 (2)
C5b0.073 (3)0.054 (3)0.039 (2)0.013 (2)0.019 (2)0.003 (2)
C6b0.060 (3)0.059 (3)0.044 (2)0.013 (2)0.008 (2)0.000 (2)
C7b0.049 (2)0.053 (3)0.051 (2)0.007 (2)0.017 (2)0.001 (2)
C8b0.053 (2)0.048 (3)0.047 (2)0.008 (2)0.015 (2)0.004 (2)
C9b0.056 (3)0.090 (4)0.048 (2)0.003 (3)0.020 (2)0.000 (3)
C10b0.059 (3)0.077 (3)0.062 (3)0.005 (3)0.026 (2)0.004 (3)
C11b0.076 (3)0.114 (5)0.064 (3)0.005 (3)0.039 (2)0.005 (3)
C12b0.053 (3)0.074 (3)0.056 (3)0.013 (2)0.011 (2)0.013 (2)
Geometric parameters (Å, º) top
O1a—C2a1.319 (5)C6b—C7b1.401 (5)
O1a—C1a1.443 (5)C7b—C8b1.396 (5)
O2a—C2a1.182 (5)C7b—C12b1.467 (6)
O3a—C6a1.332 (5)C8b—C9b1.499 (5)
O4a—C12a1.219 (4)C9b—C10b1.501 (5)
O5a—C12a1.320 (5)C10b—C11b1.498 (6)
O5a—C10a1.458 (5)O3a—H3a0.82
C2a—C3a1.481 (5)C1a—H1aa0.96
C3a—C4a1.387 (6)C1a—H1ab0.96
C3a—C8a1.396 (5)C1a—H1ac0.96
C4a—C5a1.358 (6)C4a—H4a0.93
C5a—C6a1.387 (6)C5a—H5a0.93
C6a—C7a1.401 (5)C9a—H9aa0.97
C7a—C8a1.409 (5)C9a—H9ab0.97
C7a—C12a1.473 (5)C10a—H10a0.98
C8a—C9a1.501 (5)C11a—H11a0.96
C9a—C10a1.491 (5)C11a—H11b0.96
C10a—C11a1.500 (5)C11a—H11c0.96
O1b—C2b1.318 (5)O3b—H3b0.82
O1b—C1b1.444 (5)C1b—H1ba0.96
O2b—C2b1.191 (5)C1b—H1bb0.96
O3b—C6b1.348 (5)C1b—H1bc0.96
O4b—C12b1.220 (5)C4b—H4b0.93
O5b—C12b1.319 (5)C5b—H5b0.93
O5b—C10b1.465 (6)C9b—H9ba0.97
C2b—C3b1.471 (5)C9b—H9bb0.97
C3b—C4b1.388 (5)C10b—H10b0.98
C3b—C8b1.394 (5)C11b—H11d0.96
C4b—C5b1.359 (6)C11b—H11e0.96
C5b—C6b1.377 (6)C11b—H11f0.96
C2a—O1a—C1a118.0 (3)O5b—C12b—C7b119.6 (4)
C12a—O5a—C10a118.0 (3)C6a—O3a—H3a109.5
O1a—C2a—O2a121.9 (4)O1a—C1a—H1aa109.5
O1a—C2a—C3a115.0 (3)O1a—C1a—H1ab109.5
O2a—C2a—C3a123.1 (5)H1aa—C1a—H1ab109.5
C4a—C3a—C8a118.7 (4)O1a—C1a—H1ac109.5
C4a—C3a—C2a114.8 (4)H1aa—C1a—H1ac109.5
C8a—C3a—C2a126.5 (4)H1ab—C1a—H1ac109.5
C5a—C4a—C3a122.8 (4)C5a—C4a—H4a118.6
C4a—C5a—C6a120.0 (4)C3a—C4a—H4a118.6
O3a—C6a—C5a117.1 (4)C4a—C5a—H5a120.0
O3a—C6a—C7a124.2 (4)C6a—C5a—H5a120.0
C5a—C6a—C7a118.7 (4)C10a—C9a—H9aa109.1
C6a—C7a—C8a121.0 (3)C8a—C9a—H9aa109.1
C6a—C7a—C12a117.6 (4)C10a—C9a—H9ab109.1
C8a—C7a—C12a121.4 (4)C8a—C9a—H9ab109.1
C3a—C8a—C7a118.8 (3)H9aa—C9a—H9ab107.9
C3a—C8a—C9a125.8 (3)O5a—C10a—H10a108.5
C7a—C8a—C9a115.4 (3)C9a—C10a—H10a108.5
C10a—C9a—C8a112.4 (3)C11a—C10a—H10a108.5
O5a—C10a—C9a110.9 (3)C10a—C11a—H11a109.5
O5a—C10a—C11a106.2 (3)C10a—C11a—H11b109.5
C9a—C10a—C11a113.9 (4)H11a—C11a—H11b109.5
O4a—C12a—O5a117.3 (3)C10a—C11a—H11c109.5
O4a—C12a—C7a123.2 (4)H11a—C11a—H11c109.5
O5a—C12a—C7a119.5 (4)H11b—C11a—H11c109.5
C2b—O1b—C1b116.8 (3)C6b—O3b—H3b109.5
C12b—O5b—C10b118.9 (3)O1b—C1b—H1ba109.5
O1b—C2b—O2b120.3 (4)O1b—C1b—H1bb109.5
O1b—C2b—C3b112.7 (3)H1ba—C1b—H1bb109.5
O2b—C2b—C3b126.9 (4)O1b—C1b—H1bc109.5
C4b—C3b—C8b118.0 (4)H1ba—C1b—H1bc109.5
C4b—C3b—C2b120.0 (3)H1bb—C1b—H1bc109.5
C8b—C3b—C2b122.0 (3)C5b—C4b—H4b118.4
C5b—C4b—C3b123.1 (4)C3b—C4b—H4b118.4
C4b—C5b—C6b119.4 (4)C4b—C5b—H5b120.3
O3b—C6b—C5b117.9 (4)C6b—C5b—H5b120.3
O3b—C6b—C7b122.5 (4)C8b—C9b—H9ba109.3
C5b—C6b—C7b119.5 (4)C10b—C9b—H9ba109.3
C8b—C7b—C6b120.4 (3)C8b—C9b—H9bb109.3
C8b—C7b—C12b120.8 (4)C10b—C9b—H9bb109.3
C6b—C7b—C12b118.8 (4)H9ba—C9b—H9bb108.0
C3b—C8b—C7b119.6 (3)O5b—C10b—H10b109.1
C3b—C8b—C9b124.5 (4)C11b—C10b—H10b109.1
C7b—C8b—C9b115.9 (3)C9b—C10b—H10b109.1
C8b—C9b—C10b111.6 (3)C10b—C11b—H11d109.5
O5b—C10b—C11b106.5 (4)C10b—C11b—H11e109.5
O5b—C10b—C9b109.5 (4)H11d—C11b—H11e109.5
C11b—C10b—C9b113.5 (4)C10b—C11b—H11f109.5
O4b—C12b—O5b118.2 (4)H11d—C11b—H11f109.5
O4b—C12b—C7b122.2 (4)H11e—C11b—H11f109.5
C1a—O1a—C2a—O2a0.1 (7)C1b—O1b—C2b—O2b0.7 (9)
C1a—O1a—C2a—C3a179.9 (4)C1b—O1b—C2b—C3b179.2 (5)
O2a—C2a—C3a—C4a4.4 (7)O2b—C2b—C3b—C4b178.0 (6)
O1a—C2a—C3a—C4a175.5 (4)O1b—C2b—C3b—C4b2.1 (6)
O2a—C2a—C3a—C8a174.5 (5)O2b—C2b—C3b—C8b3.6 (8)
O1a—C2a—C3a—C8a5.7 (6)O1b—C2b—C3b—C8b176.3 (4)
C8a—C3a—C4a—C5a1.2 (7)C8b—C3b—C4b—C5b1.4 (6)
C2a—C3a—C4a—C5a179.9 (5)C2b—C3b—C4b—C5b177.1 (4)
C3a—C4a—C5a—C6a0.7 (9)C3b—C4b—C5b—C6b1.5 (7)
C4a—C5a—C6a—O3a178.7 (6)C4b—C5b—C6b—O3b176.0 (4)
C4a—C5a—C6a—C7a0.2 (8)C4b—C5b—C6b—C7b3.4 (7)
O3a—C6a—C7a—C8a178.6 (5)O3b—C6b—C7b—C8b176.8 (4)
C5a—C6a—C7a—C8a0.3 (7)C5b—C6b—C7b—C8b2.5 (6)
O3a—C6a—C7a—C12a1.4 (8)O3b—C6b—C7b—C12b1.3 (7)
C5a—C6a—C7a—C12a176.9 (5)C5b—C6b—C7b—C12b179.3 (4)
C4a—C3a—C8a—C7a1.2 (6)C4b—C3b—C8b—C7b2.2 (6)
C2a—C3a—C8a—C7a180.0 (4)C2b—C3b—C8b—C7b176.2 (4)
C4a—C3a—C8a—C9a179.0 (4)C4b—C3b—C8b—C9b178.5 (4)
C2a—C3a—C8a—C9a2.2 (7)C2b—C3b—C8b—C9b3.0 (7)
C6a—C7a—C8a—C3a0.8 (6)C6b—C7b—C8b—C3b0.3 (6)
C12a—C7a—C8a—C3a176.3 (4)C12b—C7b—C8b—C3b177.8 (4)
C6a—C7a—C8a—C9a178.8 (4)C6b—C7b—C8b—C9b179.6 (4)
C12a—C7a—C8a—C9a1.7 (6)C12b—C7b—C8b—C9b1.5 (6)
C3a—C8a—C9a—C10a153.0 (4)C3b—C8b—C9b—C10b148.4 (4)
C7a—C8a—C9a—C10a29.2 (5)C7b—C8b—C9b—C10b32.4 (6)
C12a—O5a—C10a—C9a48.5 (5)C12b—O5b—C10b—C11b169.4 (4)
C12a—O5a—C10a—C11a172.8 (4)C12b—O5b—C10b—C9b46.3 (6)
C8a—C9a—C10a—O5a53.3 (4)C8b—C9b—C10b—O5b54.8 (5)
C8a—C9a—C10a—C11a173.1 (4)C8b—C9b—C10b—C11b173.7 (4)
C10a—O5a—C12a—O4a163.2 (4)C10b—O5b—C12b—O4b167.1 (4)
C10a—O5a—C12a—C7a17.5 (6)C10b—O5b—C12b—C7b12.7 (7)
C6a—C7a—C12a—O4a6.8 (7)C8b—C7b—C12b—O4b167.2 (4)
C8a—C7a—C12a—O4a170.4 (4)C6b—C7b—C12b—O4b11.0 (7)
C6a—C7a—C12a—O5a174.0 (4)C8b—C7b—C12b—O5b13.0 (7)
C8a—C7a—C12a—O5a8.8 (6)C6b—C7b—C12b—O5b168.9 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3a—H3a···O4a0.821.862.578 (4)145
O3b—H3b···O4b0.821.842.565 (4)146
 

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