(2RS,3SR,5RS,6SR)-Bicyclo­[2.2.1]heptane-2,3,5,6-tetryl tetra­acetate

In the title compound, C₁₅H₂₀O₈, 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.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](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

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Computing details

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

Crystal data

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) Å^3	0.35 × 0.34 × 0.19 mm
Z = 4

Data collection

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

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.099	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.312	H-atom parameters constrained
S = 0.93	w = 1/[σ^2(Fo^2) + (0.1627P)^2] where P = (Fo^2 + 2Fc^2)/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

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 (Ų)

	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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)

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···O5^i	0.98	2.51	3.428 (7)	156
C13—H13B···O6^ii	0.96	2.51	3.287 (8)	138
C14—H14B···O8^iii	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.