cis-Per­hydro-1,4-benzodioxin-2,3-dione

The title compound, C₈H₁₀O₄, crystallizes in the non-centrosymmetric space group Pna2₁ with two mol­ecules in the asymmetric unit. The structure is characterized by fused cyclo­hexyl and cyclic diester rings. There is a twist of 60° about the ring fusion. The mol­ecules are characterized by an average C=O bond of 1.199 (8) Å, an average sp² C-O bond of 1.328 (8) Å, and an average sp³ C-O bond of 1.469 (8) Å.

Key indicators

• Single-crystal X-ray study
• T = 110 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.061
• wR factor = 0.141
• Data-to-parameter ratio = 8.9

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT432_ALERT_2_B Short Inter X...Y Contact  O1A    ..  C1B     ..       2.79 Ang.

Alert level C
PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size .......       0.65 mm
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.01
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          5
PLAT369_ALERT_2_C Long   C(sp2)-C(sp2) Bond  C1A    -   C8A    ...       1.56 Ang.
PLAT369_ALERT_2_C Long   C(sp2)-C(sp2) Bond  C1B    -   C8B    ...       1.55 Ang.
PLAT432_ALERT_2_C Short Inter X...Y Contact  O2B    ..  C1A     ..       2.98 Ang.

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           27.53
           From the CIF: _reflns_number_total               1930
           Count of symmetry unique reflns         1956
           Completeness (_total/calc)             98.67%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured         0
           Fraction of Friedel pairs measured     0.000
           Are heavy atom types Z>Si present           no

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

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   5 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion

---

Computing details

Data collection: SMART (Bruker, 1999); cell refinement: SAINT-Plus (Bruker, 1999); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1999); software used to prepare material for publication: WinGX (Farrugia, 1999).

(I)

Crystal data

C8H10O4	F(000) = 720
Mr = 170.16	Dx = 1.451 Mg m^−3
Orthorhombic, Pna21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 54 reflections
a = 12.088 (5) Å	θ = 5.2–46.1°
b = 20.492 (9) Å	µ = 0.12 mm^−1
c = 6.289 (3) Å	T = 110 K
V = 1557.8 (12) Å^3	Needle, colorless
Z = 8	0.65 × 0.25 × 0.05 mm

Data collection

Bruker SMART 1000 CCD diffractometer	Rint = 0.033
ω andφ scans	θmax = 27.5°, θmin = 2.0°
9120 measured reflections	h = −15→14
1930 independent reflections	k = −23→26
1657 reflections with I > 2σ(I)	l = −8→6

Refinement

Refinement on F^2	1 restraint
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.061	w = 1/[σ^2(Fo^2) + (0.0926P)^2 + 0.117P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.141	(Δ/σ)max < 0.001
S = 1.11	Δρmax = 0.50 e Å^−3
1930 reflections	Δρmin = −0.25 e Å^−3
217 parameters

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C1A	0.7569 (2)	0.68040 (15)	0.3566 (5)	0.0262 (7)
O1A	0.85182 (18)	0.67086 (12)	0.3130 (5)	0.0347 (6)
O2A	0.7573 (2)	0.79222 (12)	0.2519 (5)	0.0411 (7)
O3A	0.69505 (17)	0.63568 (10)	0.4524 (4)	0.0294 (5)
C2A	0.5870 (2)	0.65713 (15)	0.5332 (6)	0.0270 (7)
H2A	0.5977	0.6866	0.6582	0.032*
C3A	0.5253 (3)	0.59582 (16)	0.6016 (6)	0.0315 (8)
H311	0.4568	0.6085	0.6772	0.038*
H312	0.572	0.5707	0.7019	0.038*
C4A	0.4954 (3)	0.55234 (15)	0.4118 (6)	0.0343 (8)
H411	0.5638	0.5342	0.3488	0.041*
H412	0.4491	0.5155	0.461	0.041*
C5A	0.4326 (3)	0.59113 (16)	0.2434 (6)	0.0323 (8)
H511	0.3613	0.6061	0.3034	0.039*
H512	0.4164	0.5624	0.1207	0.039*
C6A	0.4992 (3)	0.65043 (15)	0.1670 (6)	0.0306 (7)
H611	0.5684	0.6358	0.0975	0.037*
H612	0.4555	0.6756	0.0623	0.037*
C7A	0.5263 (2)	0.69313 (15)	0.3587 (6)	0.0284 (7)
H7A	0.4549	0.7094	0.419	0.034*
O4A	0.59147 (17)	0.74990 (10)	0.2932 (5)	0.0328 (5)
C8A	0.7007 (2)	0.74630 (15)	0.2972 (6)	0.0303 (7)
O1B	0.2605 (2)	0.90774 (14)	0.8997 (5)	0.0426 (6)
O2B	0.3060 (2)	0.77847 (12)	0.8009 (5)	0.0432 (7)
C1B	0.3529 (3)	0.88706 (18)	0.9114 (5)	0.0314 (7)
O3B	0.43689 (18)	0.92364 (11)	0.9785 (4)	0.0301 (5)
C2B	0.5397 (2)	0.88891 (16)	1.0296 (6)	0.0275 (7)
H2B	0.5277	0.8598	1.1552	0.033*
C3B	0.6265 (3)	0.94048 (16)	1.0826 (6)	0.0300 (7)
H321	0.693	0.9187	1.1412	0.036*
H322	0.5969	0.97	1.1935	0.036*
C4B	0.6600 (3)	0.98098 (17)	0.8881 (6)	0.0345 (8)
H421	0.5971	1.0089	0.8446	0.041*
H422	0.7226	1.0098	0.9264	0.041*
C5B	0.6933 (3)	0.93794 (18)	0.7046 (7)	0.0378 (8)
H521	0.7605	0.9131	0.7437	0.045*
H522	0.7116	0.9655	0.5802	0.045*
C6B	0.6007 (3)	0.89001 (18)	0.6436 (6)	0.0338 (8)
H621	0.5343	0.9143	0.5966	0.041*
H622	0.6254	0.8616	0.5253	0.041*
C7B	0.5732 (3)	0.84855 (16)	0.8389 (6)	0.0304 (7)
H7B	0.641	0.8233	0.8781	0.036*
O4B	0.4844 (2)	0.80134 (11)	0.7919 (4)	0.0354 (6)
C8B	0.3796 (3)	0.81694 (17)	0.8320 (6)	0.0330 (8)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1A	0.0209 (14)	0.0308 (15)	0.0269 (17)	0.0008 (12)	−0.0035 (12)	−0.0050 (13)
O1A	0.0240 (11)	0.0416 (13)	0.0386 (14)	0.0013 (9)	−0.0001 (11)	−0.0045 (12)
O2A	0.0330 (13)	0.0353 (13)	0.0550 (18)	−0.0066 (10)	0.0022 (12)	0.0062 (12)
O3A	0.0227 (11)	0.0299 (11)	0.0358 (14)	0.0025 (9)	−0.0008 (10)	0.0005 (10)
C2A	0.0239 (15)	0.0264 (15)	0.0306 (17)	0.0003 (12)	0.0009 (13)	−0.0035 (13)
C3A	0.0310 (17)	0.0324 (17)	0.0311 (19)	−0.0046 (13)	−0.0007 (14)	0.0023 (14)
C4A	0.0356 (17)	0.0252 (15)	0.042 (2)	−0.0017 (14)	−0.0058 (16)	−0.0019 (15)
C5A	0.0286 (16)	0.0315 (16)	0.037 (2)	0.0015 (13)	−0.0048 (14)	−0.0054 (14)
C6A	0.0261 (15)	0.0331 (17)	0.0324 (19)	0.0057 (13)	−0.0038 (14)	−0.0028 (14)
C7A	0.0204 (14)	0.0258 (15)	0.039 (2)	0.0011 (11)	0.0021 (13)	−0.0019 (14)
O4A	0.0258 (11)	0.0271 (10)	0.0454 (14)	−0.0013 (9)	0.0000 (11)	0.0042 (11)
C8A	0.0239 (15)	0.0313 (15)	0.0358 (18)	−0.0002 (12)	0.0001 (15)	−0.0022 (16)
O1B	0.0265 (12)	0.0565 (15)	0.0447 (16)	0.0037 (11)	−0.0042 (11)	−0.0010 (13)
O2B	0.0459 (14)	0.0423 (13)	0.0413 (16)	−0.0155 (12)	−0.0138 (13)	0.0055 (14)
C1B	0.0289 (17)	0.0434 (18)	0.0218 (16)	−0.0037 (14)	−0.0005 (13)	0.0056 (15)
O3B	0.0227 (11)	0.0331 (11)	0.0343 (13)	0.0034 (9)	−0.0019 (9)	0.0002 (10)
C2B	0.0214 (15)	0.0306 (16)	0.0304 (17)	0.0031 (13)	−0.0036 (13)	0.0041 (13)
C3B	0.0260 (16)	0.0349 (17)	0.0291 (17)	0.0002 (13)	−0.0040 (13)	0.0001 (14)
C4B	0.0295 (16)	0.0325 (16)	0.041 (2)	−0.0038 (14)	0.0005 (15)	0.0047 (16)
C5B	0.0307 (18)	0.0416 (19)	0.041 (2)	0.0045 (15)	0.0087 (16)	0.0084 (16)
C6B	0.0343 (18)	0.0382 (18)	0.0288 (18)	0.0040 (15)	0.0042 (15)	−0.0019 (15)
C7B	0.0294 (16)	0.0283 (14)	0.0333 (19)	0.0002 (14)	−0.0019 (14)	−0.0007 (14)
O4B	0.0383 (13)	0.0328 (12)	0.0351 (14)	−0.0027 (10)	−0.0036 (12)	−0.0015 (11)
C8B	0.0385 (18)	0.0363 (18)	0.0240 (18)	−0.0028 (15)	−0.0067 (14)	0.0052 (15)

Geometric parameters (Å, º)

C1A—O1A	1.196 (4)	O1B—C1B	1.197 (4)
C1A—O3A	1.327 (4)	O2B—C8B	1.205 (4)
C1A—C8A	1.557 (4)	C1B—O3B	1.331 (4)
O2A—C8A	1.197 (4)	C1B—C8B	1.555 (5)
O3A—C2A	1.468 (4)	O3B—C2B	1.467 (4)
C2A—C7A	1.512 (5)	C2B—C7B	1.512 (5)
C2A—C3A	1.524 (4)	C2B—C3B	1.526 (4)
C2A—H2A	1	C2B—H2B	1
C3A—C4A	1.533 (5)	C3B—C4B	1.532 (5)
C3A—H311	0.99	C3B—H321	0.99
C3A—H312	0.99	C3B—H322	0.99
C4A—C5A	1.526 (5)	C4B—C5B	1.508 (6)
C4A—H411	0.99	C4B—H421	0.99
C4A—H412	0.99	C4B—H422	0.99
C5A—C6A	1.535 (5)	C5B—C6B	1.537 (5)
C5A—H511	0.99	C5B—H521	0.99
C5A—H512	0.99	C5B—H522	0.99
C6A—C7A	1.525 (5)	C6B—C7B	1.530 (5)
C6A—H611	0.99	C6B—H621	0.99
C6A—H612	0.99	C6B—H622	0.99
C7A—O4A	1.464 (4)	C7B—O4B	1.475 (4)
C7A—H7A	1	C7B—H7B	1
O4A—C8A	1.323 (4)	O4B—C8B	1.331 (4)
O1A—C1A—O3A	122.1 (3)	O1B—C1B—O3B	122.1 (3)
O1A—C1A—C8A	120.3 (3)	O1B—C1B—C8B	120.1 (3)
O3A—C1A—C8A	117.5 (3)	O3B—C1B—C8B	117.6 (3)
C1A—O3A—C2A	116.8 (2)	C1B—O3B—C2B	116.2 (3)
O3A—C2A—C7A	109.1 (3)	O3B—C2B—C7B	108.6 (3)
O3A—C2A—C3A	106.6 (2)	O3B—C2B—C3B	107.1 (3)
C7A—C2A—C3A	111.7 (3)	C7B—C2B—C3B	111.6 (3)
O3A—C2A—H2A	109.8	O3B—C2B—H2B	109.8
C7A—C2A—H2A	109.8	C7B—C2B—H2B	109.8
C3A—C2A—H2A	109.8	C3B—C2B—H2B	109.8
C2A—C3A—C4A	112.0 (3)	C2B—C3B—C4B	112.5 (3)
C2A—C3A—H311	109.2	C2B—C3B—H321	109.1
C4A—C3A—H311	109.2	C4B—C3B—H321	109.1
C2A—C3A—H312	109.2	C2B—C3B—H322	109.1
C4A—C3A—H312	109.2	C4B—C3B—H322	109.1
H311—C3A—H312	107.9	H321—C3B—H322	107.8
C5A—C4A—C3A	110.8 (3)	C5B—C4B—C3B	111.4 (3)
C5A—C4A—H411	109.5	C5B—C4B—H421	109.3
C3A—C4A—H411	109.5	C3B—C4B—H421	109.3
C5A—C4A—H412	109.5	C5B—C4B—H422	109.3
C3A—C4A—H412	109.5	C3B—C4B—H422	109.3
H411—C4A—H412	108.1	H421—C4B—H422	108
C4A—C5A—C6A	111.6 (3)	C4B—C5B—C6B	111.7 (3)
C4A—C5A—H511	109.3	C4B—C5B—H521	109.3
C6A—C5A—H511	109.3	C6B—C5B—H521	109.3
C4A—C5A—H512	109.3	C4B—C5B—H522	109.3
C6A—C5A—H512	109.3	C6B—C5B—H522	109.3
H511—C5A—H512	108	H521—C5B—H522	107.9
C7A—C6A—C5A	108.6 (3)	C7B—C6B—C5B	108.2 (3)
C7A—C6A—H611	110	C7B—C6B—H621	110.1
C5A—C6A—H611	110	C5B—C6B—H621	110.1
C7A—C6A—H612	110	C7B—C6B—H622	110.1
C5A—C6A—H612	110	C5B—C6B—H622	110.1
H611—C6A—H612	108.3	H621—C6B—H622	108.4
O4A—C7A—C2A	109.3 (3)	O4B—C7B—C2B	108.8 (3)
O4A—C7A—C6A	110.4 (3)	O4B—C7B—C6B	111.2 (3)
C2A—C7A—C6A	113.4 (3)	C2B—C7B—C6B	113.0 (3)
O4A—C7A—H7A	107.8	O4B—C7B—H7B	107.9
C2A—C7A—H7A	107.8	C2B—C7B—H7B	107.9
C6A—C7A—H7A	107.8	C6B—C7B—H7B	107.9
C8A—O4A—C7A	119.2 (2)	C8B—O4B—C7B	119.8 (3)
O2A—C8A—O4A	121.5 (3)	O2B—C8B—O4B	121.0 (3)
O2A—C8A—C1A	119.3 (3)	O2B—C8B—C1B	120.2 (3)
O4A—C8A—C1A	119.2 (3)	O4B—C8B—C1B	118.7 (3)
O1A—C1A—O3A—C2A	168.9 (3)	O1B—C1B—O3B—C2B	167.0 (3)
C8A—C1A—O3A—C2A	−12.4 (4)	C8B—C1B—O3B—C2B	−17.2 (4)
C1A—O3A—C2A—C7A	50.2 (3)	C1B—O3B—C2B—C7B	54.3 (4)
C1A—O3A—C2A—C3A	170.9 (3)	C1B—O3B—C2B—C3B	174.9 (3)
O3A—C2A—C3A—C4A	−67.4 (3)	O3B—C2B—C3B—C4B	−68.3 (3)
C7A—C2A—C3A—C4A	51.6 (4)	C7B—C2B—C3B—C4B	50.4 (4)
C2A—C3A—C4A—C5A	−53.5 (4)	C2B—C3B—C4B—C5B	−52.2 (4)
C3A—C4A—C5A—C6A	57.2 (4)	C3B—C4B—C5B—C6B	56.8 (4)
C4A—C5A—C6A—C7A	−57.4 (4)	C4B—C5B—C6B—C7B	−58.3 (4)
O3A—C2A—C7A—O4A	−60.0 (3)	O3B—C2B—C7B—O4B	−60.3 (3)
C3A—C2A—C7A—O4A	−177.6 (3)	C3B—C2B—C7B—O4B	−178.1 (3)
O3A—C2A—C7A—C6A	63.7 (3)	O3B—C2B—C7B—C6B	63.8 (4)
C3A—C2A—C7A—C6A	−53.9 (4)	C3B—C2B—C7B—C6B	−54.0 (4)
C5A—C6A—C7A—O4A	179.1 (2)	C5B—C6B—C7B—O4B	179.9 (3)
C5A—C6A—C7A—C2A	56.0 (3)	C5B—C6B—C7B—C2B	57.1 (4)
C2A—C7A—O4A—C8A	33.6 (4)	C2B—C7B—O4B—C8B	31.9 (4)
C6A—C7A—O4A—C8A	−91.9 (4)	C6B—C7B—O4B—C8B	−93.3 (4)
C7A—O4A—C8A—O2A	−177.4 (4)	C7B—O4B—C8B—O2B	−177.8 (3)
C7A—O4A—C8A—C1A	4.1 (5)	C7B—O4B—C8B—C1B	4.8 (5)
O1A—C1A—C8A—O2A	−16.6 (5)	O1B—C1B—C8B—O2B	−15.7 (5)
O3A—C1A—C8A—O2A	164.7 (3)	O3B—C1B—C8B—O2B	168.5 (3)
O1A—C1A—C8A—O4A	161.9 (3)	O1B—C1B—C8B—O4B	161.8 (3)
O3A—C1A—C8A—O4A	−16.8 (5)	O3B—C1B—C8B—O4B	−14.0 (5)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C2B—H2B···O4A^i	1.00	2.53	3.355 (4)	139
C2B—H2B···O1A^ii	1.00	2.43	3.136 (4)	127
C5A—H511···O2A^iii	0.99	2.45	3.195 (4)	131

Symmetry codes: (i) x, y, z+1; (ii) x−1/2, −y+3/2, z+1; (iii) x−1/2, −y+3/2, z.