(2-exo,7-exo,9-endo,10-endo)-11-Oxatri­cyclo­[6.2.1.0^2,7]­undec-4-ene-9,10-diyl di­acetate

The title compound, C₁₄H₁₈O₅, shows a non-planar geometry.

Key indicators

• Single-crystal X-ray study
• T = 150 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.032
• wR factor = 0.084
• Data-to-parameter ratio = 12.2

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.30 Ratio

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   2 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   1 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

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

(2-exo,7-exo,9-endo,10-endo)-11-Oxatricyclo[6.2.1.0^2,7]undec-4-ene-9,10-diyl diacetate

Crystal data

C14H18O5	F(000) = 568
Mr = 266.28	Dx = 1.352 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2988 reflections
a = 5.8430 (3) Å	θ = 1.6–27.6°
b = 12.8501 (8) Å	µ = 0.10 mm^−1
c = 17.5767 (11) Å	T = 150 K
β = 97.449 (5)°	Prism, colorless
V = 1308.58 (13) Å^3	0.57 × 0.40 × 0.27 mm
Z = 4

Data collection

Stoe IPDS-II diffractometer	2988 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus	2624 reflections with I > 2σ(I)
Plane graphite monochromator	Rint = 0.027
Detector resolution: 6.67 pixels mm^-1	θmax = 27.5°, θmin = 2.0°
ω scans	h = −7→7
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	k = −16→16
Tmin = 0.944, Tmax = 0.973	l = −22→22
18334 measured reflections

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)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.084	All H-atom parameters refined
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0437P)^2 + 0.2964P] where P = (Fo^2 + 2Fc^2)/3
2988 reflections	(Δ/σ)max < 0.001
244 parameters	Δρmax = 0.22 e Å^−3
0 restraints	Δρmin = −0.18 e Å^−3

Special details

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F² for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > 2σ(F²) is used only for calculating -R-factor-obs 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
O1	0.48132 (12)	0.63003 (6)	0.45262 (4)	0.0281 (2)
O2	0.57775 (12)	0.58123 (6)	0.26059 (4)	0.0260 (2)
O3	0.82973 (12)	0.45963 (5)	0.35702 (4)	0.0246 (2)
O4	0.23150 (14)	0.60181 (7)	0.19010 (5)	0.0419 (3)
O5	0.59197 (13)	0.34430 (6)	0.29131 (5)	0.0358 (3)
C1	0.47188 (16)	0.56786 (8)	0.32919 (6)	0.0248 (3)
C2	0.46256 (17)	0.66961 (8)	0.37478 (6)	0.0246 (3)
C3	0.68437 (16)	0.73200 (7)	0.37466 (5)	0.0231 (2)
C4	0.6587 (2)	0.84389 (8)	0.40308 (7)	0.0314 (3)
C5	0.8881 (2)	0.89057 (9)	0.43211 (7)	0.0346 (3)
C6	1.0378 (2)	0.83403 (9)	0.47737 (7)	0.0358 (3)
C7	0.9761 (2)	0.72545 (9)	0.49856 (6)	0.0320 (3)
C8	0.85803 (16)	0.66476 (8)	0.42874 (5)	0.0236 (3)
C9	0.70085 (17)	0.57803 (8)	0.45189 (6)	0.0258 (3)
C10	0.63198 (17)	0.50064 (8)	0.38717 (6)	0.0250 (3)
C11	0.43822 (19)	0.59999 (8)	0.19485 (6)	0.0289 (3)
C12	0.5770 (2)	0.61705 (11)	0.13010 (7)	0.0381 (3)
C13	0.78279 (18)	0.37948 (8)	0.30738 (6)	0.0269 (3)
C14	0.9934 (2)	0.34322 (10)	0.27563 (8)	0.0355 (3)
H1	0.319 (2)	0.5365 (10)	0.3166 (7)	0.026 (3)*
H2	0.318 (2)	0.7090 (9)	0.3641 (7)	0.026 (3)*
H3	0.728 (2)	0.7353 (9)	0.3235 (7)	0.023 (3)*
H4A	0.576 (2)	0.8847 (11)	0.3605 (8)	0.040 (4)*
H4B	0.561 (2)	0.8441 (11)	0.4457 (8)	0.037 (3)*
H5	0.923 (3)	0.9619 (12)	0.4184 (8)	0.043 (4)*
H6	1.187 (3)	0.8609 (12)	0.4988 (9)	0.047 (4)*
H7A	1.110 (3)	0.6863 (12)	0.5212 (8)	0.042 (4)*
H7B	0.868 (2)	0.7301 (10)	0.5371 (8)	0.033 (3)*
H8	0.980 (2)	0.6348 (10)	0.3999 (7)	0.026 (3)*
H9	0.749 (2)	0.5464 (10)	0.5016 (7)	0.027 (3)*
H10	0.546 (2)	0.4437 (10)	0.4060 (7)	0.028 (3)*
H12A	0.541 (3)	0.6835 (17)	0.1108 (11)	0.076 (6)*
H12B	0.533 (3)	0.5668 (15)	0.0900 (11)	0.068 (5)*
H12C	0.737 (3)	0.6092 (14)	0.1444 (11)	0.067 (5)*
H13A	1.009 (3)	0.3832 (15)	0.2316 (12)	0.069 (5)*
H13B	0.975 (3)	0.2718 (15)	0.2627 (10)	0.062 (5)*
H13C	1.133 (3)	0.3556 (12)	0.3101 (9)	0.049 (4)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0282 (4)	0.0288 (4)	0.0302 (4)	0.0049 (3)	0.0148 (3)	0.0055 (3)
O2	0.0252 (3)	0.0291 (4)	0.0240 (3)	−0.0011 (3)	0.0041 (3)	0.0023 (3)
O3	0.0241 (3)	0.0234 (3)	0.0276 (3)	0.0022 (3)	0.0081 (3)	0.0002 (3)
O4	0.0317 (4)	0.0475 (5)	0.0439 (5)	−0.0001 (4)	−0.0047 (4)	0.0021 (4)
O5	0.0283 (4)	0.0332 (4)	0.0461 (5)	−0.0027 (3)	0.0059 (3)	−0.0059 (3)
C1	0.0210 (4)	0.0253 (5)	0.0292 (5)	−0.0021 (4)	0.0072 (4)	0.0027 (4)
C2	0.0220 (4)	0.0248 (5)	0.0280 (5)	0.0024 (4)	0.0067 (4)	0.0041 (4)
C3	0.0239 (4)	0.0237 (4)	0.0220 (4)	−0.0005 (4)	0.0045 (3)	0.0024 (4)
C4	0.0339 (5)	0.0239 (5)	0.0352 (6)	0.0023 (4)	0.0000 (5)	0.0007 (4)
C5	0.0402 (6)	0.0279 (5)	0.0356 (6)	−0.0052 (4)	0.0048 (5)	−0.0059 (4)
C6	0.0329 (6)	0.0373 (6)	0.0363 (6)	−0.0027 (5)	0.0011 (5)	−0.0118 (5)
C7	0.0324 (5)	0.0366 (6)	0.0258 (5)	0.0073 (4)	−0.0010 (4)	−0.0038 (4)
C8	0.0235 (4)	0.0259 (5)	0.0223 (4)	0.0030 (4)	0.0060 (4)	0.0006 (4)
C9	0.0291 (5)	0.0265 (5)	0.0236 (5)	0.0064 (4)	0.0103 (4)	0.0056 (4)
C10	0.0250 (5)	0.0226 (4)	0.0296 (5)	0.0020 (4)	0.0121 (4)	0.0046 (4)
C11	0.0336 (5)	0.0218 (5)	0.0297 (5)	−0.0014 (4)	−0.0017 (4)	−0.0007 (4)
C12	0.0478 (7)	0.0391 (6)	0.0266 (5)	−0.0025 (5)	0.0024 (5)	0.0027 (5)
C13	0.0283 (5)	0.0240 (5)	0.0289 (5)	0.0013 (4)	0.0062 (4)	0.0009 (4)
C14	0.0310 (6)	0.0361 (6)	0.0413 (6)	0.0012 (5)	0.0121 (5)	−0.0086 (5)

Geometric parameters (Å, º)

O1—C2	1.450 (1)	C13—C14	1.4903 (16)
O1—C9	1.448 (1)	C1—H1	0.979 (12)
O2—C1	1.435 (1)	C2—H2	0.982 (12)
O2—C11	1.347 (1)	C3—H3	0.967 (12)
O3—C10	1.433 (1)	C4—H4A	0.987 (14)
O3—C13	1.355 (1)	C4—H4B	0.999 (13)
O4—C11	1.200 (1)	C5—H5	0.976 (16)
O5—C13	1.202 (1)	C6—H6	0.967 (17)
C1—C2	1.5382 (15)	C7—H7A	0.971 (17)
C1—C10	1.5533 (14)	C7—H7B	0.986 (13)
C2—C3	1.5242 (14)	C8—H8	1.003 (12)
C3—C4	1.5358 (14)	C9—H9	0.972 (12)
C3—C8	1.5587 (13)	C10—H10	0.970 (12)
C4—C5	1.4965 (17)	C12—H12A	0.93 (2)
C5—C6	1.3211 (17)	C12—H12B	0.966 (19)
C6—C7	1.5001 (16)	C12—H12C	0.942 (18)
C7—C8	1.5397 (14)	C14—H13A	0.94 (2)
C8—C9	1.5323 (14)	C14—H13B	0.948 (19)
C9—C10	1.5252 (15)	C14—H13C	0.964 (17)
C11—C12	1.4967 (16)
O1···C7^i	3.3894 (14)	C14···H3^ix	2.889 (12)
O1···C9^ii	3.4002 (13)	H1···O4	2.370 (12)
O1···C10^ii	3.4162 (13)	H1···H13C^i	2.56 (2)
O2···C8	3.3637 (12)	H2···H4B	2.561 (18)
O2···O3	2.6144 (10)	H2···H8^i	2.351 (17)
O2···O5	3.0913 (11)	H3···O2	2.379 (12)
O2···C13	2.9287 (13)	H3···C14^vii	2.889 (12)
O3···O2	2.6144 (10)	H3···H13B^vii	2.49 (2)
O5···C11^iii	3.1555 (13)	H4A···O5^v	2.770 (14)
O5···C1	3.0512 (13)	H4A···C11^v	2.930 (14)
O5···O2	3.0913 (11)	H4B···O1	2.795 (14)
O1···H7A^i	2.713 (17)	H4B···C7	2.913 (13)
O1···H10^ii	2.684 (12)	H4B···H2	2.561 (18)
O1···H4B	2.795 (14)	H4B···H6^i	2.49 (2)
O1···H9^ii	2.807 (13)	H5···O4^v	2.690 (15)
O1···H7B	2.845 (13)	H6···H4B^vi	2.49 (2)
O2···H3	2.379 (12)	H6···C12^x	3.039 (17)
O3···H7A^iv	2.833 (15)	H6···H12B^x	2.59 (2)
O3···H8	2.497 (13)	H7A···O1^vi	2.713 (17)
O4···H1	2.370 (12)	H7A···O3^iv	2.833 (15)
O4···H13B^v	2.679 (19)	H7B···O1	2.845 (13)
O4···H5^iii	2.690 (15)	H7B···C4	2.904 (14)
O4···H12C^i	2.898 (18)	H7B···H9	2.517 (18)
O5···H10	2.431 (12)	H8···O3	2.497 (13)
O5···H13C^i	2.748 (18)	H8···C2^vi	2.944 (12)
O5···H4A^iii	2.770 (14)	H8···H2^vi	2.351 (17)
O5···H12A^iii	2.86 (2)	H9···H7B	2.517 (18)
C1···O5	3.0512 (13)	H9···O1^ii	2.807 (13)
C7···O1^vi	3.3894 (14)	H9···H10^ii	2.520 (17)
C8···O2	3.3637 (12)	H10···O5	2.431 (12)
C9···O1^ii	3.4002 (13)	H10···O1^ii	2.684 (12)
C10···O1^ii	3.4162 (13)	H10···C9^ii	3.055 (12)
C11···O5^v	3.1555 (13)	H10···H9^ii	2.520 (17)
C13···O2	2.9287 (13)	H12A···O5^v	2.86 (2)
C2···H8^i	2.944 (12)	H12B···C4^iii	3.084 (19)
C4···H12B^v	3.084 (19)	H12B···H6^viii	2.59 (2)
C4···H7B	2.904 (14)	H12C···O4^vi	2.898 (18)
C5···H13A^vii	3.02 (2)	H13A···C5^ix	3.02 (2)
C7···H4B	2.913 (13)	H13B···O4^iii	2.679 (19)
C9···H10^ii	3.055 (12)	H13B···H3^ix	2.49 (2)
C11···H4A^iii	2.930 (14)	H13C···O5^vi	2.748 (18)
C12···H6^viii	3.039 (17)	H13C···H1^vi	2.56 (2)
C2—O1—C9	96.44 (7)	C4—C3—H3	108.1 (7)
C1—O2—C11	117.61 (8)	C8—C3—H3	111.2 (7)
C10—O3—C13	114.35 (8)	C3—C4—H4A	108.0 (8)
O2—C1—C2	112.59 (8)	C3—C4—H4B	109.6 (8)
O2—C1—C10	109.23 (8)	C5—C4—H4A	112.0 (8)
C2—C1—C10	100.95 (8)	C5—C4—H4B	108.5 (8)
O1—C2—C1	100.95 (8)	H4A—C4—H4B	107.2 (11)
O1—C2—C3	103.03 (8)	C4—C5—H5	119.9 (10)
C1—C2—C3	111.03 (8)	C6—C5—H5	121.5 (10)
C2—C3—C4	111.90 (8)	C5—C6—H6	122.1 (9)
C2—C3—C8	101.19 (7)	C7—C6—H6	118.0 (9)
C4—C3—C8	113.82 (8)	C6—C7—H7A	112.1 (10)
C3—C4—C5	111.42 (9)	C6—C7—H7B	108.1 (8)
C4—C5—C6	118.60 (10)	C8—C7—H7A	108.6 (9)
C5—C6—C7	119.96 (11)	C8—C7—H7B	108.5 (8)
C6—C7—C8	111.75 (9)	H7A—C7—H7B	107.7 (12)
C3—C8—C7	113.22 (8)	C3—C8—H8	110.7 (7)
C3—C8—C9	101.53 (7)	C7—C8—H8	108.8 (7)
C7—C8—C9	112.26 (8)	C9—C8—H8	110.2 (7)
O1—C9—C8	103.23 (8)	O1—C9—H9	109.8 (7)
O1—C9—C10	99.16 (8)	C8—C9—H9	115.4 (7)
C8—C9—C10	112.67 (8)	C10—C9—H9	114.6 (8)
O3—C10—C1	114.07 (8)	O3—C10—H10	109.1 (7)
O3—C10—C9	111.61 (8)	C1—C10—H10	110.4 (7)
C1—C10—C9	101.83 (8)	C9—C10—H10	109.6 (7)
O2—C11—O4	123.71 (10)	C11—C12—H12A	107.0 (11)
O2—C11—C12	110.56 (9)	C11—C12—H12B	109.7 (11)
O4—C11—C12	125.72 (10)	C11—C12—H12C	113.5 (12)
O3—C13—O5	122.77 (10)	H12A—C12—H12B	108.7 (17)
O3—C13—C14	111.77 (9)	H12A—C12—H12C	111.4 (16)
O5—C13—C14	125.46 (10)	H12B—C12—H12C	106.5 (16)
O2—C1—H1	109.9 (7)	C13—C14—H13A	108.0 (11)
C2—C1—H1	112.0 (7)	C13—C14—H13B	108.6 (11)
C10—C1—H1	112.0 (7)	C13—C14—H13C	112.7 (10)
O1—C2—H2	108.6 (7)	H13A—C14—H13B	110.5 (16)
C1—C2—H2	115.2 (7)	H13A—C14—H13C	105.2 (15)
C3—C2—H2	116.1 (7)	H13B—C14—H13C	111.8 (14)
C2—C3—H3	110.6 (7)
C2—O1—C9—C8	54.87 (8)	O1—C2—C3—C8	35.61 (9)
C2—O1—C9—C10	−61.17 (8)	O1—C2—C3—C4	−85.94 (9)
C9—O1—C2—C1	58.52 (8)	C4—C3—C8—C7	−2.12 (12)
C9—O1—C2—C3	−56.31 (8)	C8—C3—C4—C5	43.60 (12)
C11—O2—C1—C10	154.62 (9)	C2—C3—C8—C7	−122.32 (9)
C1—O2—C11—O4	−3.18 (15)	C4—C3—C8—C9	118.42 (9)
C1—O2—C11—C12	177.21 (9)	C2—C3—C8—C9	−1.78 (9)
C11—O2—C1—C2	−94.10 (10)	C2—C3—C4—C5	157.56 (9)
C10—O3—C13—C14	177.64 (9)	C3—C4—C5—C6	−44.92 (15)
C13—O3—C10—C1	−74.50 (10)	C4—C5—C6—C7	0.03 (17)
C13—O3—C10—C9	170.77 (8)	C5—C6—C7—C8	43.92 (15)
C10—O3—C13—O5	−1.55 (14)	C6—C7—C8—C3	−39.92 (12)
O2—C1—C10—O3	−6.08 (11)	C6—C7—C8—C9	−154.16 (9)
C10—C1—C2—O1	−32.23 (9)	C3—C8—C9—C10	73.39 (9)
C2—C1—C10—C9	−4.51 (9)	C7—C8—C9—C10	−165.39 (9)
C10—C1—C2—C3	76.46 (9)	C7—C8—C9—O1	88.63 (9)
O2—C1—C2—O1	−148.58 (8)	C3—C8—C9—O1	−32.59 (9)
C2—C1—C10—O3	−124.88 (8)	C8—C9—C10—O3	53.31 (11)
O2—C1—C10—C9	114.30 (9)	O1—C9—C10—C1	39.80 (9)
O2—C1—C2—C3	−39.89 (11)	O1—C9—C10—O3	161.89 (8)
C1—C2—C3—C4	166.74 (8)	C8—C9—C10—C1	−68.77 (10)
C1—C2—C3—C8	−71.71 (9)

Symmetry codes: (i) x−1, y, z; (ii) −x+1, −y+1, −z+1; (iii) −x+1, y−1/2, −z+1/2; (iv) −x+2, −y+1, −z+1; (v) −x+1, y+1/2, −z+1/2; (vi) x+1, y, z; (vii) −x+2, y+1/2, −z+1/2; (viii) x−1, −y+3/2, z−1/2; (ix) −x+2, y−1/2, −z+1/2; (x) x+1, −y+3/2, z+1/2.