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The title compound, C18H20O10, has crystallographically imposed \overline{4} mol­ecular symmetry. It is a dioxoadamantane with its two C=O bonds lying along the twofold axis. It is symmetrically substituted with four methoxy­carbonyl groups, and the ester groups form CH2-C-C=O torsion angles of 26.21 (7)° with the adamantane core.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806025980/cf2047sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806025980/cf2047Isup2.hkl
Contains datablock I

CCDC reference: 618150

Key indicators

  • Single-crystal X-ray study
  • T = 110 K
  • Mean [sigma](C-C) = 0.001 Å
  • R factor = 0.042
  • wR factor = 0.127
  • Data-to-parameter ratio = 55.6

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT230_ALERT_2_C Hirshfeld Test Diff for C2 - C4 .. 5.65 su PLAT764_ALERT_4_C Overcomplete CIF Bond List Detected (Rep/Expd) . 1.11 Ratio
Alert level G REFLT03_ALERT_1_G ALERT: Expected hkl max differ from CIF values From the CIF: _diffrn_reflns_theta_max 45.30 From the CIF: _reflns_number_total 3672 From the CIF: _diffrn_reflns_limit_ max hkl 25. 17. 21. From the CIF: _diffrn_reflns_limit_ min hkl -25. -17. -21. TEST1: Expected hkl limits for theta max Calculated maximum hkl 25. 25. 21. Calculated minimum hkl -25. -25. -21.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: COLLECT (Nonius, 2000); cell refinement: DENZO and SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO and SCALEPACK; program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX publication routines (Farrugia, 1999).

Tetramethyl 2,6-dioxoadamantane-1,3,5,7-tetracarboxylate top
Crystal data top
C18H20O10Dx = 1.494 Mg m3
Mr = 396.34Mo Kα radiation, λ = 0.71073 Å
Tetragonal, I41/aCell parameters from 3719 reflections
Hall symbol: -I 4adθ = 2.5–45.3°
a = 12.7635 (8) ŵ = 0.12 mm1
c = 10.8158 (6) ÅT = 110 K
V = 1761.97 (18) Å3Bicapped square prism, colorless
Z = 40.43 × 0.40 × 0.40 mm
F(000) = 832
Data collection top
Nonius KappaCCD
diffractometer with an Oxford Cryosystems Cryostream cooler
Rint = 0.024
ω scans with κ offsetsθmax = 45.3°, θmin = 4°
22791 measured reflectionsh = 2525
3672 independent reflectionsk = 1717
2858 reflections with I > 2σ(I)l = 2121
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.042 w = 1/[σ2(Fo2) + (0.063P)2 + 0.5219P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.127(Δ/σ)max = 0.001
S = 1.06Δρmax = 0.45 e Å3
3672 reflectionsΔρmin = 0.32 e Å3
66 parameters
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
O10.50.750.89856 (5)0.01866 (11)
O20.70033 (4)0.59472 (4)0.82004 (5)0.02193 (10)
O30.54614 (3)0.51067 (3)0.83016 (4)0.01676 (8)
C10.50.750.78628 (6)0.01146 (10)
C20.55318 (4)0.66568 (3)0.70754 (4)0.01060 (8)
C30.46702 (4)0.61431 (4)0.62789 (4)0.01150 (8)
H3A0.41310.5830.68230.014*
H3B0.49790.55760.57720.014*
C40.60900 (4)0.58740 (4)0.79163 (5)0.01262 (8)
C50.59624 (5)0.43064 (5)0.90454 (7)0.02149 (11)
H5A0.65040.39550.85550.032*
H5B0.54380.37920.93110.032*
H5C0.62840.46310.97740.032*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0318 (3)0.0154 (2)0.00875 (19)0.0012 (2)00
O20.01919 (18)0.01829 (17)0.0283 (2)0.00477 (14)0.01265 (16)0.00807 (16)
O30.01609 (15)0.01436 (14)0.01984 (18)0.00030 (12)0.00064 (13)0.00717 (13)
C10.0152 (2)0.0098 (2)0.0094 (2)0.00152 (17)00
C20.01213 (15)0.00969 (14)0.00997 (15)0.00025 (11)0.00151 (12)0.00039 (11)
C30.01228 (15)0.01049 (14)0.01174 (17)0.00030 (12)0.00167 (12)0.00088 (12)
C40.01545 (17)0.01037 (15)0.01203 (17)0.00070 (12)0.00238 (13)0.00091 (12)
C50.0249 (3)0.0158 (2)0.0237 (3)0.00219 (18)0.0004 (2)0.00891 (18)
Geometric parameters (Å, º) top
O1—C11.2144 (9)C2—C3ii1.5467 (7)
O2—C41.2092 (7)C3—C2iii1.5466 (7)
O3—C41.3329 (6)C3—H3A0.99
O3—C51.4489 (7)C3—H3B0.99
C1—C2i1.5310 (6)C5—H5A0.98
C1—C21.5310 (6)C5—H5B0.98
C2—C41.5274 (6)C5—H5C0.98
C2—C31.5432 (6)
C4—O3—C5115.21 (5)C2—C3—H3B109.6
O1—C1—C2i123.79 (3)C2iii—C3—H3B109.6
O1—C1—C2123.79 (3)H3A—C3—H3B108.1
C2i—C1—C2112.41 (5)O2—C4—O3123.90 (5)
C4—C2—C1109.60 (4)O2—C4—C2123.39 (4)
C4—C2—C3112.76 (4)O3—C4—C2112.71 (4)
C1—C2—C3107.05 (3)O3—C5—H5A109.5
C4—C2—C3ii108.38 (4)O3—C5—H5B109.5
C1—C2—C3ii109.66 (3)H5A—C5—H5B109.5
C3—C2—C3ii109.37 (3)O3—C5—H5C109.5
C2—C3—C2iii110.25 (4)H5A—C5—H5C109.5
C2—C3—H3A109.6H5B—C5—H5C109.5
C2iii—C3—H3A109.6
O1—C1—C2—C42.77 (4)C5—O3—C4—O23.50 (9)
C2i—C1—C2—C4177.23 (4)C5—O3—C4—C2176.61 (5)
O1—C1—C2—C3119.83 (3)C1—C2—C4—O293.44 (6)
C2i—C1—C2—C360.17 (3)C3—C2—C4—O2147.43 (6)
O1—C1—C2—C3ii121.63 (3)C3ii—C2—C4—O226.21 (7)
C2i—C1—C2—C3ii58.38 (3)C1—C2—C4—O386.45 (5)
C4—C2—C3—C2iii178.45 (4)C3—C2—C4—O332.68 (6)
C1—C2—C3—C2iii60.95 (5)C3ii—C2—C4—O3153.91 (4)
C3ii—C2—C3—C2iii57.78 (4)
Symmetry codes: (i) x+1, y+3/2, z; (ii) y+5/4, x+1/4, z+5/4; (iii) y1/4, x+5/4, z+5/4.
 

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