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Both carboxyl groups in the title mol­ecule, C9H12O4, have gauche orientations [relative to the (HOOC-)C-C(-COOH) bond] and participate in hydrogen bonds, linking the mol­ecules into an infinite chain.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802019086/cv6157sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536802019086/cv6157Isup2.hkl
Contains datablock I

CCDC reference: 200777

Key indicators

  • Single-crystal X-ray study
  • T = 295 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.044
  • wR factor = 0.113
  • Data-to-parameter ratio = 14.1

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry








Computing details top

Data collection: SMART (Siemens, 1995); cell refinement: SMART; data reduction: SAINT (Siemens, 1995); program(s) used to solve structure: SHELXS86 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1998); software used to prepare material for publication: SHELXTL.

bicyclo[2.2.1]heptane-exo-cis-2,3-dicarboxylic acid top
Crystal data top
C9H12O4F(000) = 784
Mr = 184.19Dx = 1.368 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
a = 15.327 (2) ÅCell parameters from 443 reflections
b = 11.503 (2) Åθ = 10.2–20.8°
c = 10.643 (2) ŵ = 0.11 mm1
β = 107.57 (1)°T = 295 K
V = 1788.9 (5) Å3Prism, colourless
Z = 80.40 × 0.26 × 0.22 mm
Data collection top
Siemens SMART 1K CCD area-detector
diffractometer
1895 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.030
Graphite monochromatorθmax = 29.0°, θmin = 2.3°
Detector resolution: 8 pixels mm-1h = 1720
ω scansk = 1515
6844 measured reflectionsl = 1414
2358 independent reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.044All H-atom parameters refined
wR(F2) = 0.113 w = 1/[σ2(Fo2) + (0.0351P)2 + 1.2379P]
where P = (Fo2 + 2Fc2)/3
S = 1.10(Δ/σ)max < 0.001
2358 reflectionsΔρmax = 0.26 e Å3
167 parametersΔρmin = 0.17 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0175 (12)
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 (15 s exposure) covering 0.3° in ω. Crystal to detector distance 4.52 cm. Crystal decay was monitored by repeating 50 initial frames at the end of data collection and comparing 112 duplicate reflections.

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
C10.28662 (10)0.21617 (16)0.82808 (15)0.0461 (4)
H10.2852 (13)0.2597 (17)0.9044 (19)0.057 (5)*
C20.20857 (9)0.24928 (13)0.70414 (13)0.0364 (3)
H20.2223 (11)0.3203 (14)0.6617 (16)0.042 (4)*
C30.20419 (9)0.14329 (12)0.60976 (13)0.0360 (3)
H30.2193 (11)0.1681 (13)0.5296 (15)0.040 (4)*
C40.27957 (11)0.06231 (15)0.69545 (18)0.0486 (4)
H40.2725 (13)0.0185 (18)0.6611 (19)0.062 (5)*
C50.37253 (11)0.1166 (2)0.7035 (2)0.0605 (5)
H510.4220 (16)0.059 (2)0.747 (2)0.082 (7)*
H520.3776 (15)0.137 (2)0.616 (2)0.078 (7)*
C60.37689 (11)0.22366 (19)0.79305 (18)0.0565 (5)
H610.4283 (15)0.2176 (18)0.872 (2)0.071 (6)*
H620.3813 (14)0.2983 (19)0.7476 (19)0.064 (6)*
C70.27357 (12)0.08507 (17)0.83437 (17)0.0543 (5)
H710.3228 (15)0.0479 (17)0.902 (2)0.068 (6)*
H720.2138 (13)0.0620 (16)0.8476 (18)0.057 (5)*
C80.11836 (10)0.27697 (13)0.72779 (14)0.0394 (3)
C90.11375 (9)0.08057 (12)0.56364 (13)0.0370 (3)
O10.05313 (8)0.30401 (12)0.62254 (11)0.0558 (3)
H010.006 (2)0.305 (3)0.642 (3)0.124 (10)*
O20.10967 (8)0.27751 (12)0.83953 (11)0.0556 (3)
O30.08654 (9)0.06000 (12)0.43818 (11)0.0581 (4)
H030.029 (2)0.021 (2)0.415 (3)0.108 (9)*
O40.07213 (8)0.04906 (12)0.63960 (11)0.0584 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0348 (7)0.0667 (10)0.0328 (7)0.0098 (7)0.0044 (5)0.0004 (7)
C20.0353 (7)0.0409 (7)0.0318 (6)0.0091 (6)0.0085 (5)0.0007 (5)
C30.0331 (6)0.0414 (7)0.0347 (7)0.0075 (5)0.0119 (5)0.0004 (5)
C40.0372 (8)0.0464 (9)0.0602 (10)0.0003 (6)0.0116 (7)0.0052 (7)
C50.0338 (8)0.0809 (13)0.0666 (12)0.0001 (8)0.0146 (8)0.0041 (10)
C60.0327 (8)0.0805 (13)0.0506 (9)0.0158 (8)0.0039 (7)0.0045 (9)
C70.0384 (8)0.0699 (11)0.0498 (9)0.0024 (8)0.0061 (7)0.0243 (8)
C80.0392 (7)0.0429 (8)0.0350 (7)0.0068 (6)0.0094 (6)0.0028 (6)
C90.0366 (7)0.0387 (7)0.0353 (7)0.0070 (5)0.0105 (5)0.0012 (5)
O10.0415 (6)0.0796 (9)0.0447 (6)0.0082 (6)0.0104 (5)0.0124 (6)
O20.0439 (6)0.0870 (9)0.0367 (6)0.0062 (6)0.0133 (5)0.0108 (6)
O30.0527 (7)0.0839 (9)0.0390 (6)0.0303 (6)0.0157 (5)0.0146 (6)
O40.0529 (7)0.0826 (9)0.0413 (6)0.0347 (6)0.0165 (5)0.0052 (6)
Geometric parameters (Å, º) top
C1—C71.525 (3)C5—C61.546 (3)
C1—C21.5373 (19)C5—H511.01 (2)
C1—C61.540 (2)C5—H520.99 (2)
C1—H10.960 (19)C6—H610.97 (2)
C2—C81.512 (2)C6—H621.00 (2)
C2—C31.568 (2)C7—H710.97 (2)
C2—H20.986 (17)C7—H721.003 (19)
C3—C91.5074 (18)C8—O21.2361 (17)
C3—C41.549 (2)C8—O11.2942 (18)
C3—H30.991 (16)C9—O41.2261 (17)
C4—C71.531 (3)C9—O31.2948 (17)
C4—C51.534 (2)O1—H010.99 (3)
C4—H40.99 (2)O3—H030.95 (3)
C7—C1—C2101.78 (12)C4—C5—H51108.5 (13)
C7—C1—C6101.84 (15)C6—C5—H51110.4 (13)
C2—C1—C6107.56 (13)C4—C5—H52112.3 (13)
C7—C1—H1116.3 (11)C6—C5—H52113.0 (14)
C2—C1—H1112.7 (12)H51—C5—H52109.3 (18)
C6—C1—H1115.2 (11)C1—C6—C5103.28 (14)
C8—C2—C1115.04 (12)C1—C6—H61110.1 (13)
C8—C2—C3113.95 (11)C5—C6—H61110.5 (13)
C1—C2—C3103.23 (12)C1—C6—H62111.3 (12)
C8—C2—H2103.6 (9)C5—C6—H62112.5 (12)
C1—C2—H2112.3 (9)H61—C6—H62109.1 (17)
C3—C2—H2108.9 (9)C1—C7—C494.57 (12)
C9—C3—C4110.68 (12)C1—C7—H71112.6 (12)
C9—C3—C2115.98 (11)C4—C7—H71112.3 (13)
C4—C3—C2102.14 (12)C1—C7—H72113.9 (11)
C9—C3—H3106.7 (9)C4—C7—H72114.4 (11)
C4—C3—H3110.7 (9)H71—C7—H72108.6 (16)
C2—C3—H3110.6 (9)O2—C8—O1123.51 (14)
C7—C4—C5101.64 (14)O2—C8—C2122.05 (13)
C7—C4—C3102.37 (13)O1—C8—C2114.39 (12)
C5—C4—C3107.66 (14)O4—C9—O3123.80 (13)
C7—C4—H4119.0 (11)O4—C9—C3122.49 (12)
C5—C4—H4113.4 (11)O3—C9—C3113.67 (12)
C3—C4—H4111.6 (11)C8—O1—H01110.0 (16)
C4—C5—C6103.02 (14)C9—O3—H03109.5 (16)
O1—C8—C2—C360.67 (17)C2—C3—C9—O3133.33 (14)
C8—C2—C3—C93.63 (17)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H01···O2i0.99 (3)1.68 (3)2.6628 (16)168 (3)
O3—H03···O4ii0.95 (3)1.69 (3)2.6378 (16)175 (3)
Symmetry codes: (i) x, y, z+3/2; (ii) x, y, z+1.
 

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