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In the title compound, C
15H
20O
8, the bicyclo system has a six-membered ring with a boat conformation. Three types of intermolecular C—H
O hydrogen bonds and one intramolecular C—H
O hydrogen bond are present in the crystal structure.
Supporting information
CCDC reference: 601230
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.007 Å
- R factor = 0.099
- wR factor = 0.312
- Data-to-parameter ratio = 15.5
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT026_ALERT_3_B Ratio Observed / Unique Reflections too Low .... 38 Perc.
Alert level C
RFACR01_ALERT_3_C The value of the weighted R factor is > 0.25
Weighted R factor given 0.312
RINTA01_ALERT_3_C The value of Rint is greater than 0.10
Rint given 0.124
PLAT020_ALERT_3_C The value of Rint is greater than 0.10 ......... 0.12
PLAT084_ALERT_2_C High R2 Value .................................. 0.31
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature 293 K
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature . 293 K
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C10
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C11
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 7
Alert level G
REFLT03_ALERT_1_G ALERT: Expected hkl max differ from CIF values
From the CIF: _diffrn_reflns_theta_max 28.00
From the CIF: _reflns_number_total 3216
From the CIF: _diffrn_reflns_limit_ max hkl 17. 15. 12.
From the CIF: _diffrn_reflns_limit_ min hkl -12. -12. -12.
TEST1: Expected hkl limits for theta max
Calculated maximum hkl 17. 15. 14.
Calculated minimum hkl -17. -15. -14.
0 ALERT level A = In general: serious problem
1 ALERT level B = Potentially serious problem
9 ALERT level C = Check and explain
1 ALERT level G = General alerts; check
3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
3 ALERT type 2 Indicator that the structure model may be wrong or deficient
5 ALERT type 3 Indicator that the structure quality may be low
0 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Bruker, 1997); cell refinement: SMART; data reduction: SAINT (Bruker, 1997) and SHELXTL (Sheldrick, 1997b); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).
(2RS,3SR,5RS,6SR)-Bicyclo[2.2.1]heptane-2,3,5,6-tetryl tetraacetate
top
Crystal data top
C15H20O8 | F(000) = 696 |
Mr = 328.31 | Dx = 1.316 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 1210 reflections |
a = 13.5589 (15) Å | θ = 1.5–28.0° |
b = 11.6620 (12) Å | µ = 0.11 mm−1 |
c = 10.7025 (11) Å | T = 293 K |
β = 101.758 (2)° | Prism, colourless |
V = 1656.8 (3) Å3 | 0.35 × 0.34 × 0.19 mm |
Z = 4 | |
Data collection top
Bruker SMART CCD area-detector diffractometer | 1210 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.124 |
Graphite monochromator | θmax = 28.0°, θmin = 1.5° |
φ and ω scans | h = −12→17 |
7428 measured reflections | k = −12→15 |
3216 independent reflections | l = −12→12 |
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)] = 0.099 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.312 | H-atom parameters constrained |
S = 0.93 | w = 1/[σ2(Fo2) + (0.1627P)2] where P = (Fo2 + 2Fc2)/3 |
3216 reflections | (Δ/σ)max = 0.021 |
208 parameters | Δρmax = 0.30 e Å−3 |
0 restraints | Δρmin = −0.44 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
O2 | 0.7153 (2) | 0.6604 (3) | 0.0378 (3) | 0.0922 (10) | |
O3 | 0.8070 (3) | 1.0925 (3) | −0.0424 (3) | 0.0912 (10) | |
O4 | 0.9058 (2) | 1.0005 (3) | 0.1682 (3) | 0.0883 (9) | |
O1 | 0.5789 (3) | 0.7736 (3) | −0.1182 (3) | 0.0981 (10) | |
C4 | 0.6356 (4) | 0.8489 (4) | −0.0224 (4) | 0.0855 (13) | |
H4 | 0.5902 | 0.8968 | 0.0159 | 0.103* | |
C2 | 0.7079 (4) | 0.9224 (4) | −0.0778 (4) | 0.0885 (13) | |
H2 | 0.6825 | 0.9475 | −0.1659 | 0.106* | |
C6 | 0.7445 (4) | 1.0193 (4) | 0.0166 (4) | 0.0860 (12) | |
H6 | 0.6879 | 1.0618 | 0.0381 | 0.103* | |
C7 | 0.8045 (4) | 0.9533 (4) | 0.1344 (4) | 0.0842 (13) | |
H7 | 0.7702 | 0.9568 | 0.2066 | 0.101* | |
O8 | 0.9195 (3) | 0.9179 (4) | 0.3595 (4) | 0.1200 (14) | |
C11 | 0.6433 (4) | 0.5853 (5) | 0.0534 (5) | 0.0945 (14) | |
O6 | 0.5766 (3) | 0.6074 (4) | 0.1058 (4) | 0.1212 (14) | |
C3 | 0.8072 (4) | 0.8298 (4) | 0.0839 (4) | 0.0845 (13) | |
H3 | 0.8645 | 0.7839 | 0.1276 | 0.101* | |
O7 | 0.7978 (3) | 1.2320 (3) | 0.0984 (4) | 0.1200 (13) | |
O5 | 0.4518 (3) | 0.8988 (4) | −0.1539 (4) | 0.1328 (15) | |
C5 | 0.7054 (3) | 0.7762 (4) | 0.0815 (5) | 0.0856 (12) | |
H5 | 0.6856 | 0.7792 | 0.1645 | 0.103* | |
C9 | 0.9565 (4) | 0.9734 (4) | 0.2889 (4) | 0.0911 (14) | |
C8 | 0.8293 (4) | 1.1981 (4) | 0.0085 (6) | 0.0976 (15) | |
C1 | 0.8038 (4) | 0.8489 (4) | −0.0584 (5) | 0.0932 (14) | |
H1A | 0.7947 | 0.7784 | −0.1075 | 0.112* | |
H1B | 0.8618 | 0.8907 | −0.0746 | 0.112* | |
C15 | 1.0580 (4) | 1.0242 (5) | 0.3109 (5) | 0.1099 (17) | |
H15A | 1.0662 | 1.0658 | 0.2363 | 0.165* | |
H15B | 1.1076 | 0.9645 | 0.3285 | 0.165* | |
H15C | 1.0663 | 1.0756 | 0.3824 | 0.165* | |
C10 | 0.4862 (5) | 0.8078 (6) | −0.1731 (6) | 0.1042 (16) | |
C13 | 0.6589 (5) | 0.4735 (5) | −0.0095 (7) | 0.125 (2) | |
H13A | 0.7194 | 0.4774 | −0.0427 | 0.187* | |
H13B | 0.6025 | 0.4589 | −0.0780 | 0.187* | |
H13C | 0.6645 | 0.4127 | 0.0520 | 0.187* | |
C14 | 0.8960 (5) | 1.2611 (5) | −0.0618 (6) | 0.1203 (19) | |
H14A | 0.9102 | 1.2137 | −0.1293 | 0.181* | |
H14B | 0.9578 | 1.2803 | −0.0043 | 0.181* | |
H14C | 0.8630 | 1.3301 | −0.0973 | 0.181* | |
C12 | 0.4338 (5) | 0.7181 (6) | −0.2618 (6) | 0.131 (2) | |
H12A | 0.4768 | 0.6523 | −0.2590 | 0.196* | |
H12B | 0.4185 | 0.7480 | −0.3472 | 0.196* | |
H12C | 0.3725 | 0.6963 | −0.2365 | 0.196* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O2 | 0.070 (2) | 0.0844 (18) | 0.120 (2) | −0.0046 (16) | 0.0142 (19) | 0.0013 (17) |
O3 | 0.093 (2) | 0.0864 (19) | 0.093 (2) | −0.0088 (17) | 0.0161 (18) | 0.0063 (16) |
O4 | 0.070 (2) | 0.096 (2) | 0.098 (2) | −0.0065 (16) | 0.0147 (17) | 0.0011 (16) |
O1 | 0.083 (2) | 0.092 (2) | 0.110 (2) | −0.0019 (18) | −0.002 (2) | −0.0020 (18) |
C4 | 0.071 (3) | 0.089 (3) | 0.092 (3) | −0.003 (2) | 0.006 (3) | −0.002 (2) |
C2 | 0.083 (3) | 0.089 (3) | 0.091 (3) | 0.003 (3) | 0.012 (3) | 0.003 (2) |
C6 | 0.077 (3) | 0.089 (3) | 0.093 (3) | 0.006 (2) | 0.020 (3) | −0.002 (2) |
C7 | 0.074 (3) | 0.094 (3) | 0.084 (3) | 0.007 (2) | 0.016 (2) | 0.001 (2) |
O8 | 0.100 (3) | 0.147 (3) | 0.107 (2) | −0.034 (2) | 0.005 (2) | 0.028 (2) |
C11 | 0.068 (3) | 0.113 (4) | 0.093 (3) | −0.009 (3) | −0.005 (3) | 0.012 (3) |
O6 | 0.104 (3) | 0.144 (3) | 0.121 (3) | −0.030 (3) | 0.034 (3) | −0.018 (2) |
C3 | 0.072 (3) | 0.090 (3) | 0.088 (3) | 0.009 (2) | 0.008 (2) | −0.002 (2) |
O7 | 0.139 (3) | 0.091 (2) | 0.135 (3) | −0.009 (2) | 0.038 (3) | −0.017 (2) |
O5 | 0.084 (3) | 0.169 (4) | 0.139 (3) | 0.020 (3) | 0.007 (2) | −0.026 (3) |
C5 | 0.074 (3) | 0.082 (3) | 0.103 (3) | −0.007 (2) | 0.021 (3) | −0.002 (2) |
C9 | 0.078 (3) | 0.103 (3) | 0.089 (3) | −0.013 (3) | 0.009 (3) | 0.000 (3) |
C8 | 0.099 (4) | 0.078 (3) | 0.111 (4) | −0.001 (3) | 0.011 (3) | −0.004 (3) |
C1 | 0.083 (4) | 0.094 (3) | 0.108 (3) | −0.006 (3) | 0.033 (3) | −0.003 (3) |
C15 | 0.094 (4) | 0.127 (4) | 0.104 (3) | −0.026 (3) | 0.010 (3) | 0.000 (3) |
C10 | 0.080 (4) | 0.117 (4) | 0.115 (4) | −0.009 (3) | 0.019 (3) | 0.001 (3) |
C13 | 0.105 (4) | 0.093 (3) | 0.169 (5) | −0.013 (3) | 0.012 (4) | −0.018 (4) |
C14 | 0.124 (5) | 0.112 (4) | 0.124 (4) | −0.032 (4) | 0.023 (4) | 0.009 (3) |
C12 | 0.110 (5) | 0.138 (5) | 0.129 (4) | −0.040 (4) | −0.009 (4) | 0.005 (4) |
Geometric parameters (Å, º) top
O2—C11 | 1.347 (6) | C3—C1 | 1.530 (6) |
O2—C5 | 1.444 (5) | C3—H3 | 0.9800 |
O3—C8 | 1.356 (6) | O7—C8 | 1.197 (6) |
O3—C6 | 1.437 (5) | O5—C10 | 1.194 (7) |
O4—C9 | 1.372 (5) | C5—H5 | 0.9800 |
O4—C7 | 1.456 (5) | C9—C15 | 1.472 (7) |
O1—C10 | 1.335 (6) | C8—C14 | 1.483 (7) |
O1—C4 | 1.446 (5) | C1—H1A | 0.9700 |
C4—C2 | 1.512 (6) | C1—H1B | 0.9700 |
C4—C5 | 1.557 (6) | C15—H15A | 0.9600 |
C4—H4 | 0.9800 | C15—H15B | 0.9600 |
C2—C6 | 1.530 (6) | C15—H15C | 0.9600 |
C2—C1 | 1.536 (7) | C10—C12 | 1.492 (8) |
C2—H2 | 0.9800 | C13—H13A | 0.9600 |
C6—C7 | 1.557 (6) | C13—H13B | 0.9600 |
C6—H6 | 0.9800 | C13—H13C | 0.9600 |
C7—C3 | 1.542 (6) | C14—H14A | 0.9600 |
C7—H7 | 0.9800 | C14—H14B | 0.9600 |
O8—C9 | 1.182 (5) | C14—H14C | 0.9600 |
C11—O6 | 1.186 (6) | C12—H12A | 0.9600 |
C11—C13 | 1.502 (8) | C12—H12B | 0.9600 |
C3—C5 | 1.510 (6) | C12—H12C | 0.9600 |
| | | |
C11—O2—C5 | 116.8 (4) | C3—C5—H5 | 112.8 |
C8—O3—C6 | 117.8 (4) | C4—C5—H5 | 112.8 |
C9—O4—C7 | 114.4 (3) | O8—C9—O4 | 122.2 (5) |
C10—O1—C4 | 116.5 (4) | O8—C9—C15 | 128.5 (5) |
O1—C4—C2 | 111.0 (4) | O4—C9—C15 | 109.3 (4) |
O1—C4—C5 | 109.5 (4) | O7—C8—O3 | 122.5 (5) |
C2—C4—C5 | 103.9 (4) | O7—C8—C14 | 126.8 (5) |
O1—C4—H4 | 110.7 | O3—C8—C14 | 110.8 (5) |
C2—C4—H4 | 110.7 | C3—C1—C2 | 93.9 (4) |
C5—C4—H4 | 110.8 | C3—C1—H1A | 112.9 |
C4—C2—C6 | 108.0 (4) | C2—C1—H1A | 112.9 |
C4—C2—C1 | 103.3 (4) | C3—C1—H1B | 112.9 |
C6—C2—C1 | 99.8 (4) | C2—C1—H1B | 112.9 |
C4—C2—H2 | 114.7 | H1A—C1—H1B | 110.4 |
C6—C2—H2 | 114.7 | C9—C15—H15A | 109.5 |
C1—C2—H2 | 114.7 | C9—C15—H15B | 109.5 |
O3—C6—C2 | 106.8 (3) | H15A—C15—H15B | 109.5 |
O3—C6—C7 | 113.1 (4) | C9—C15—H15C | 109.5 |
C2—C6—C7 | 102.5 (4) | H15A—C15—H15C | 109.5 |
O3—C6—H6 | 111.3 | H15B—C15—H15C | 109.5 |
C2—C6—H6 | 111.3 | O5—C10—O1 | 123.8 (6) |
C7—C6—H6 | 111.3 | O5—C10—C12 | 125.5 (6) |
O4—C7—C3 | 110.6 (4) | O1—C10—C12 | 110.7 (6) |
O4—C7—C6 | 108.9 (4) | C11—C13—H13A | 109.5 |
C3—C7—C6 | 102.9 (4) | C11—C13—H13B | 109.5 |
O4—C7—H7 | 111.4 | H13A—C13—H13B | 109.5 |
C3—C7—H7 | 111.4 | C11—C13—H13C | 109.5 |
C6—C7—H7 | 111.4 | H13A—C13—H13C | 109.5 |
O6—C11—O2 | 124.0 (5) | H13B—C13—H13C | 109.5 |
O6—C11—C13 | 126.2 (5) | C8—C14—H14A | 109.5 |
O2—C11—C13 | 109.7 (5) | C8—C14—H14B | 109.5 |
C5—C3—C1 | 101.6 (4) | H14A—C14—H14B | 109.5 |
C5—C3—C7 | 107.8 (4) | C8—C14—H14C | 109.5 |
C1—C3—C7 | 102.4 (4) | H14A—C14—H14C | 109.5 |
C5—C3—H3 | 114.5 | H14B—C14—H14C | 109.5 |
C1—C3—H3 | 114.5 | C10—C12—H12A | 109.5 |
C7—C3—H3 | 114.5 | C10—C12—H12B | 109.5 |
O2—C5—C3 | 104.4 (4) | H12A—C12—H12B | 109.5 |
O2—C5—C4 | 111.2 (4) | C10—C12—H12C | 109.5 |
C3—C5—C4 | 102.0 (4) | H12A—C12—H12C | 109.5 |
O2—C5—H5 | 112.8 | H12B—C12—H12C | 109.5 |
| | | |
C10—O1—C4—C2 | −98.7 (5) | O4—C7—C3—C1 | −86.9 (4) |
C10—O1—C4—C5 | 147.2 (4) | C6—C7—C3—C1 | 29.2 (5) |
O1—C4—C2—C6 | 165.7 (4) | C11—O2—C5—C3 | 165.7 (4) |
C5—C4—C2—C6 | −76.7 (4) | C11—O2—C5—C4 | −85.1 (5) |
O1—C4—C2—C1 | −89.2 (4) | C1—C3—C5—O2 | 74.7 (4) |
C5—C4—C2—C1 | 28.4 (5) | C7—C3—C5—O2 | −178.0 (3) |
C8—O3—C6—C2 | 164.8 (4) | C1—C3—C5—C4 | −41.1 (4) |
C8—O3—C6—C7 | −83.2 (5) | C7—C3—C5—C4 | 66.1 (4) |
C4—C2—C6—O3 | −175.8 (4) | O1—C4—C5—O2 | 15.5 (5) |
C1—C2—C6—O3 | 76.7 (4) | C2—C4—C5—O2 | −103.2 (4) |
C4—C2—C6—C7 | 65.1 (5) | O1—C4—C5—C3 | 126.3 (4) |
C1—C2—C6—C7 | −42.5 (4) | C2—C4—C5—C3 | 7.6 (4) |
C9—O4—C7—C3 | −85.1 (5) | C7—O4—C9—O8 | −1.3 (7) |
C9—O4—C7—C6 | 162.6 (4) | C7—O4—C9—C15 | 179.2 (4) |
O3—C6—C7—O4 | 10.8 (5) | C6—O3—C8—O7 | −1.1 (7) |
C2—C6—C7—O4 | 125.5 (4) | C6—O3—C8—C14 | 178.8 (4) |
O3—C6—C7—C3 | −106.5 (4) | C5—C3—C1—C2 | 57.1 (4) |
C2—C6—C7—C3 | 8.1 (5) | C7—C3—C1—C2 | −54.3 (4) |
C5—O2—C11—O6 | −3.9 (7) | C4—C2—C1—C3 | −51.9 (4) |
C5—O2—C11—C13 | 173.9 (4) | C6—C2—C1—C3 | 59.3 (4) |
O4—C7—C3—C5 | 166.4 (3) | C4—O1—C10—O5 | 5.5 (8) |
C6—C7—C3—C5 | −77.5 (4) | C4—O1—C10—C12 | −175.5 (4) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C1—H1B···O3 | 0.97 | 2.51 | 2.846 (6) | 100 |
C6—H6···O5i | 0.98 | 2.51 | 3.428 (7) | 156 |
C13—H13B···O6ii | 0.96 | 2.51 | 3.287 (8) | 138 |
C14—H14B···O8iii | 0.96 | 2.59 | 3.476 (8) | 154 |
Symmetry codes: (i) −x+1, −y+2, −z; (ii) −x+1, −y+1, −z; (iii) −x+2, y+1/2, −z+1/2. |
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