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The bi­cyclo­[3.1.0]­hexane fragment of the title mol­ecule, C9H12O4, adopts a boat-like conformation, with its methoxy­carbonyl substituent in the endo position. In the crystal structure, mol­ecules form centrosymmetric O—H...O hydrogen-bonded dimers, which are arranged in layers.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803021433/lh6117sup1.cif
Contains datablocks global, 1

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803021433/lh61171sup2.hkl
Contains datablock 1

CCDC reference: 226938

Key indicators

  • Single-crystal X-ray study
  • T = 120 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.036
  • wR factor = 0.096
  • Data-to-parameter ratio = 13.9

checkCIF/PLATON results

No syntax errors found



Alert level C CRYSR01_ALERT_1_C _exptl_crystal_size_rad not in the CIF when expected. PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.99 PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ?
0 ALERT level A = In general: serious problem 0 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 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 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: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Methyl exo-bicyclo[3.1.0]hexane-6,6-dicarboxylate top
Crystal data top
C9H12O4F(000) = 392
Mr = 184.19Dx = 1.395 Mg m3
Monoclinic, P21/nMelting point: 137-137.5 °C K
Hall symbol: -P 2ynMo Kα radiation, λ = 0.71073 Å
a = 9.1290 (2) ÅCell parameters from 3387 reflections
b = 8.7002 (2) Åθ = 2.9–30.4°
c = 11.6958 (3) ŵ = 0.11 mm1
β = 109.28 (1)°T = 120 K
V = 876.82 (5) Å3Spheroid, colourless
Z = 40.20 × 0.12 × 0.10 mm
Data collection top
Bruker APEX CCD
diffractometer
1972 reflections with I > 2σ(I)
Radiation source: Bede MicrosourceRint = 0.026
Graphite monochromatorθmax = 29.0°, θmin = 2.5°
ω scansh = 1212
7793 measured reflectionsk = 1111
2315 independent reflectionsl = 1515
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)] = 0.036Hydrogen site location: difference Fourier map
wR(F2) = 0.096All H-atom parameters refined
S = 1.06 w = 1/[σ2(Fo2) + (0.06P)2]
where P = (Fo2 + 2Fc2)/3
2315 reflections(Δ/σ)max = 0.001
166 parametersΔρmax = 0.40 e Å3
0 restraintsΔρmin = 0.22 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
O10.56934 (8)0.81807 (8)0.06779 (7)0.01908 (18)
O20.43344 (8)1.00819 (8)0.11562 (7)0.01799 (18)
O30.48494 (8)0.53779 (8)0.21678 (7)0.01845 (18)
O40.73269 (8)0.61765 (8)0.29348 (7)0.02120 (19)
C10.41044 (11)0.84333 (11)0.31905 (9)0.0159 (2)
C20.39190 (12)0.73181 (12)0.41298 (10)0.0197 (2)
C30.55839 (12)0.69629 (12)0.49713 (11)0.0211 (2)
C40.65681 (12)0.83671 (12)0.48726 (10)0.0194 (2)
C50.57194 (11)0.90835 (11)0.36532 (9)0.0158 (2)
C60.52596 (10)0.80223 (11)0.25450 (9)0.0144 (2)
C70.50433 (11)0.88582 (10)0.13938 (9)0.0149 (2)
C80.59577 (11)0.64477 (11)0.25921 (9)0.0149 (2)
C90.54336 (14)0.38410 (12)0.20918 (12)0.0236 (2)
H1O0.5571 (19)0.8779 (19)0.0041 (18)0.045 (4)*
H10.3215 (15)0.9056 (15)0.2706 (12)0.021 (3)*
H210.3315 (15)0.7849 (14)0.4607 (12)0.023 (3)*
H220.3327 (15)0.6383 (15)0.3752 (12)0.024 (3)*
H310.5621 (16)0.6776 (17)0.5811 (14)0.032 (4)*
H320.5989 (14)0.6017 (15)0.4717 (12)0.021 (3)*
H410.6611 (15)0.9116 (16)0.5507 (14)0.028 (3)*
H420.7641 (16)0.8085 (14)0.4976 (12)0.022 (3)*
H50.5925 (13)1.0142 (14)0.3498 (12)0.017 (3)*
H910.6165 (16)0.3547 (17)0.2865 (14)0.029 (4)*
H920.4548 (16)0.3188 (17)0.1882 (13)0.031 (4)*
H930.5964 (15)0.3841 (15)0.1523 (13)0.025 (3)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0255 (4)0.0178 (4)0.0163 (4)0.0039 (3)0.0100 (3)0.0015 (3)
O20.0191 (3)0.0172 (3)0.0183 (4)0.0040 (3)0.0070 (3)0.0035 (3)
O30.0172 (3)0.0139 (3)0.0234 (4)0.0003 (3)0.0056 (3)0.0030 (3)
O40.0165 (3)0.0175 (3)0.0293 (5)0.0018 (3)0.0072 (3)0.0015 (3)
C10.0154 (4)0.0158 (4)0.0176 (5)0.0013 (3)0.0068 (4)0.0001 (4)
C20.0198 (5)0.0203 (5)0.0210 (6)0.0008 (4)0.0094 (4)0.0022 (4)
C30.0233 (5)0.0224 (5)0.0185 (6)0.0014 (4)0.0081 (4)0.0048 (4)
C40.0195 (5)0.0219 (5)0.0156 (5)0.0002 (4)0.0043 (4)0.0001 (4)
C50.0172 (4)0.0143 (4)0.0161 (5)0.0001 (3)0.0059 (4)0.0007 (4)
C60.0147 (4)0.0134 (4)0.0156 (5)0.0009 (3)0.0055 (4)0.0003 (3)
C70.0132 (4)0.0150 (4)0.0151 (5)0.0012 (3)0.0029 (4)0.0013 (4)
C80.0173 (4)0.0141 (4)0.0142 (5)0.0002 (3)0.0065 (4)0.0008 (4)
C90.0253 (5)0.0145 (5)0.0318 (7)0.0008 (4)0.0109 (5)0.0045 (4)
Geometric parameters (Å, º) top
O1—C71.3149 (12)C3—C41.5432 (14)
O1—H1O0.885 (19)C3—H310.985 (15)
O2—C71.2291 (11)C3—H320.988 (13)
O3—C81.3434 (11)C4—C51.5143 (14)
O3—C91.4531 (12)C4—H410.979 (15)
O4—C81.2032 (12)C4—H420.978 (13)
C1—C51.5032 (13)C5—C61.5327 (14)
C1—C21.5165 (14)C5—H50.969 (12)
C1—C61.5284 (13)C6—C71.4849 (14)
C1—H10.985 (13)C6—C81.5043 (13)
C2—C31.5448 (15)C9—H910.964 (15)
C2—H211.016 (12)C9—H920.951 (15)
C2—H220.996 (14)C9—H930.944 (14)
C7—O1—H1O108.3 (11)H41—C4—H42106.6 (11)
C8—O3—C9114.41 (8)C1—C5—C4108.67 (8)
C5—C1—C2108.11 (8)C1—C5—C660.45 (6)
C5—C1—C660.73 (6)C4—C5—C6117.42 (8)
C2—C1—C6117.93 (8)C1—C5—H5121.2 (7)
C5—C1—H1121.6 (8)C4—C5—H5119.8 (8)
C2—C1—H1120.0 (8)C6—C5—H5115.5 (8)
C6—C1—H1114.6 (8)C7—C6—C8114.02 (8)
C1—C2—C3105.54 (8)C7—C6—C1115.24 (8)
C1—C2—H21108.5 (7)C8—C6—C1123.24 (8)
C3—C2—H21109.8 (8)C7—C6—C5112.89 (8)
C1—C2—H22112.0 (8)C8—C6—C5121.55 (8)
C3—C2—H22113.2 (8)C1—C6—C558.82 (6)
H21—C2—H22107.6 (10)O2—C7—O1123.98 (9)
C4—C3—C2105.58 (8)O2—C7—C6122.12 (9)
C4—C3—H31112.1 (8)O1—C7—C6113.89 (8)
C2—C3—H31111.8 (8)O4—C8—O3124.06 (9)
C4—C3—H32110.6 (7)O4—C8—C6124.87 (9)
C2—C3—H32111.2 (8)O3—C8—C6111.05 (8)
H31—C3—H32105.7 (12)O3—C9—H91110.0 (9)
C5—C4—C3105.48 (8)O3—C9—H92105.5 (9)
C5—C4—H41108.6 (8)H91—C9—H92110.5 (12)
C3—C4—H41110.4 (8)O3—C9—H93109.1 (8)
C5—C4—H42113.6 (8)H91—C9—H93107.7 (12)
C3—C4—H42112.1 (7)H92—C9—H93114.1 (12)
C5—C1—C2—C316.28 (10)C4—C5—C6—C815.43 (12)
C6—C1—C2—C349.59 (12)C4—C5—C6—C196.91 (9)
C1—C2—C3—C425.21 (11)C8—C6—C7—O2171.84 (8)
C2—C3—C4—C524.63 (11)C1—C6—C7—O220.96 (13)
C2—C1—C5—C40.89 (11)C5—C6—C7—O244.06 (12)
C6—C1—C5—C4111.55 (9)C8—C6—C7—O19.08 (12)
C2—C1—C5—C6112.44 (9)C1—C6—C7—O1159.95 (8)
C3—C4—C5—C114.87 (10)C5—C6—C7—O1135.02 (8)
C3—C4—C5—C650.85 (11)C9—O3—C8—O43.02 (14)
C5—C1—C6—C7102.56 (9)C9—O3—C8—C6175.28 (9)
C2—C1—C6—C7161.35 (9)C7—C6—C8—O488.30 (12)
C5—C1—C6—C8109.55 (10)C1—C6—C8—O4123.46 (11)
C2—C1—C6—C813.46 (14)C5—C6—C8—O452.36 (13)
C2—C1—C6—C596.09 (10)C7—C6—C8—O389.98 (10)
C1—C5—C6—C7106.59 (9)C1—C6—C8—O358.26 (12)
C4—C5—C6—C7156.50 (8)C5—C6—C8—O3129.35 (9)
C1—C5—C6—C8112.35 (10)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1O···O2i0.885 (19)1.74 (2)2.6175 (11)170.4 (16)
Symmetry code: (i) x+1, y+2, z.
 

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