Two diastereomers of ()-cis-2-(3-oxo-1,3,4,5,6,7-hexa­hydro­isobenzo­furan-1-yl)cyclo­hexane­carboxyl­ic acid

The structures are presented for both diastereomers of the title compound, C₁₅H₂₀O₄, produced by base-catalyzed self-condensation of cyclo­hexane-cis-1,2-di­carboxyl­ic anhydride in refluxing triethyl­amine. Equilibration of either diastereomer under the condensation conditions yielded the same 5:3 mixture. In the crystal, one diastereomer, (II), is ordered, while the other, (I), displays both flexional ring disorder and carboxyl disorder; both aggregate as centrosymmetric hydrogen-bonded dimers [for (I), O...O = 2.680 (2) Å; for (II), O...O = 2.635 (4) Å].

Computing details

For both compounds, data collection: XSCANS (Siemens, 1996); cell refinement: XSCANS; data reduction: XSCANS; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97; molecular graphics: SHELXL97; software used to prepare material for publication: SHELXL97.

(I) (±)-cis-2-(3-Oxo-1,3,4,5,6,7-hexahydroisobenzofuran-1-yl)- cyclohexanecarboxylic acid

Crystal data

C15H20O4	F(000) = 284
Mr = 264.32	Dx = 1.235 Mg m^−3
Triclinic, P1	Melting point = 444–446 K
a = 6.652 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.616 (4) Å	Cell parameters from 33 reflections
c = 11.038 (4) Å	θ = 3.8–13.3°
α = 66.18 (1)°	µ = 0.09 mm^−1
β = 88.20 (1)°	T = 293 K
γ = 85.61 (2)°	Rectangular prism, colorless
V = 711.0 (4) Å^3	0.60 × 0.18 × 0.16 mm
Z = 2

Data collection

Siemens P4 diffractometer	1790 reflections with I > 2σ(I)
Radiation source: normal-focus sealed tube	Rint = 0.034
Graphite monochromator	θmax = 25.0°, θmin = 2.0°
2θ/θ scans	h = −7→7
Absorption correction: numerical XPREP (Sheldrick, 1997)	k = −11→11
Tmin = 0.98, Tmax = 0.99	l = 0→13
4844 measured reflections	3 standard reflections every 97 reflections
2422 independent reflections	intensity decay: variation < 1%

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.088	H-atom parameters constrained
S = 1.01	w = 1/[σ^2(Fo^2) + (0.0272P)^2 + 0.1159P] where P = (Fo^2 + 2Fc^2)/3
2422 reflections	(Δ/σ)max = 0.01
192 parameters	Δρmax = 0.14 e Å^−3
0 restraints	Δρmin = −0.12 e Å^−3

Special details

Experimental. Crystal mounted on glass fiber using epoxy resin

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	Occ. (<1)
O1	0.80540 (18)	0.56041 (14)	0.60286 (13)	0.0579 (4)
O2	0.48334 (16)	0.64264 (11)	0.60146 (11)	0.0407 (3)
O3	0.4272 (2)	0.91003 (14)	0.65943 (12)	0.0586 (4)
O4	0.2717 (2)	0.93710 (13)	0.47315 (12)	0.0570 (4)
C1	0.2882 (2)	0.58538 (16)	0.64482 (15)	0.0359 (4)
C3	0.6301 (3)	0.53716 (18)	0.62922 (16)	0.0395 (4)
C3A	0.5355 (2)	0.40492 (17)	0.69056 (15)	0.0362 (4)
C4	0.6387 (3)	0.26234 (17)	0.73623 (17)	0.0463 (4)
C5	0.489 (3)	0.1550 (14)	0.7665 (14)	0.061 (3)	0.351 (11)
C6	0.3114 (15)	0.1823 (7)	0.8462 (14)	0.067 (3)	0.351 (11)
C5'	0.4905 (13)	0.1563 (8)	0.8223 (7)	0.0594 (15)	0.649 (11)
C6'	0.2806 (6)	0.1866 (4)	0.7606 (8)	0.0654 (15)	0.649 (11)
C7	0.1887 (3)	0.32496 (18)	0.7541 (2)	0.0552 (5)
C7A	0.3382 (2)	0.43209 (16)	0.69956 (15)	0.0367 (4)
C8	0.1894 (2)	0.64056 (16)	0.74287 (15)	0.0355 (4)
C9	0.1195 (2)	0.79612 (16)	0.67575 (16)	0.0390 (4)
C10	0.0184 (3)	0.84559 (19)	0.77873 (18)	0.0512 (5)
C11	0.1440 (3)	0.80718 (18)	0.90404 (17)	0.0512 (5)
C12	0.2033 (3)	0.65251 (18)	0.96661 (17)	0.0504 (5)
C13	0.3154 (3)	0.60468 (17)	0.86779 (16)	0.0430 (4)
C14	0.2863 (3)	0.88605 (16)	0.60161 (16)	0.0410 (4)
H1	0.2002	0.6121	0.5676	0.043*
H3	0.5059	0.9579	0.6045	0.088*	0.31 (3)
H4	0.3690	0.9821	0.4401	0.086*	0.69 (3)
H4A	0.7303	0.2578	0.6678	0.056*	0.351 (11)
H4B	0.7174	0.2436	0.8149	0.056*	0.351 (11)
H4A'	0.7579	0.2565	0.7864	0.056*	0.649 (11)
H4B'	0.6798	0.2431	0.6609	0.056*	0.649 (11)
H5A	0.5550	0.0646	0.8167	0.073*	0.351 (11)
H5B	0.4404	0.1556	0.6845	0.073*	0.351 (11)
H6A	0.3601	0.1893	0.9251	0.080*	0.351 (11)
H6B	0.2235	0.1068	0.8735	0.080*	0.351 (11)
H5'A	0.5421	0.0645	0.8330	0.071*	0.649 (11)
H5'B	0.4813	0.1582	0.9094	0.071*	0.649 (11)
H6'A	0.2897	0.1883	0.6720	0.078*	0.649 (11)
H6'B	0.1948	0.1140	0.8131	0.078*	0.649 (11)
H7A	0.1217	0.3138	0.6826	0.066*	0.351 (11)
H7B	0.0875	0.3519	0.8059	0.066*	0.351 (11)
H7A'	0.0696	0.3526	0.7001	0.066*	0.649 (11)
H7B'	0.1503	0.3157	0.8419	0.066*	0.649 (11)
H8	0.0659	0.5920	0.7731	0.043*
H9	0.0161	0.8058	0.6107	0.047*
H10A	−0.0067	0.9451	0.7377	0.061*
H10B	−0.1109	0.8059	0.8036	0.061*
H11A	0.2647	0.8578	0.8820	0.061*
H11B	0.0667	0.8334	0.9673	0.061*
H12A	0.0831	0.6023	0.9972	0.061*
H12B	0.2889	0.6319	1.0428	0.061*
H13A	0.3460	0.5056	0.9092	0.052*
H13B	0.4418	0.6485	0.8435	0.052*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0404 (8)	0.0617 (9)	0.0710 (9)	−0.0131 (6)	0.0074 (6)	−0.0250 (7)
O2	0.0421 (6)	0.0362 (6)	0.0420 (6)	−0.0092 (5)	0.0084 (5)	−0.0133 (5)
O3	0.0761 (9)	0.0606 (9)	0.0415 (7)	−0.0308 (7)	0.0040 (7)	−0.0188 (6)
O4	0.0671 (9)	0.0560 (8)	0.0349 (7)	−0.0091 (7)	−0.0014 (6)	−0.0038 (6)
C1	0.0362 (9)	0.0386 (9)	0.0336 (8)	−0.0070 (7)	0.0013 (7)	−0.0148 (7)
C3	0.0400 (10)	0.0465 (10)	0.0358 (9)	−0.0072 (8)	0.0022 (7)	−0.0201 (8)
C3A	0.0412 (10)	0.0385 (9)	0.0330 (8)	−0.0056 (7)	0.0018 (7)	−0.0183 (7)
C4	0.0509 (11)	0.0455 (11)	0.0441 (10)	0.0008 (9)	0.0005 (8)	−0.0203 (9)
C5	0.080 (6)	0.037 (4)	0.069 (8)	−0.005 (3)	0.014 (7)	−0.027 (6)
C6	0.076 (6)	0.040 (4)	0.086 (7)	−0.022 (3)	0.033 (5)	−0.025 (4)
C5'	0.072 (3)	0.036 (2)	0.065 (4)	−0.0037 (18)	0.000 (4)	−0.015 (3)
C6'	0.067 (3)	0.0391 (19)	0.093 (4)	−0.0160 (16)	0.004 (2)	−0.027 (2)
C7	0.0501 (11)	0.0438 (11)	0.0762 (14)	−0.0140 (9)	0.0143 (10)	−0.0281 (10)
C7A	0.0423 (10)	0.0372 (9)	0.0361 (9)	−0.0091 (7)	0.0037 (7)	−0.0194 (7)
C8	0.0384 (9)	0.0326 (9)	0.0348 (9)	−0.0079 (7)	0.0038 (7)	−0.0122 (7)
C9	0.0413 (9)	0.0373 (9)	0.0364 (9)	−0.0009 (7)	−0.0039 (7)	−0.0128 (7)
C10	0.0579 (12)	0.0431 (10)	0.0506 (11)	0.0040 (9)	0.0055 (9)	−0.0185 (9)
C11	0.0699 (13)	0.0437 (11)	0.0428 (10)	−0.0041 (9)	0.0098 (9)	−0.0209 (9)
C12	0.0709 (13)	0.0450 (11)	0.0347 (9)	−0.0040 (9)	0.0028 (9)	−0.0154 (8)
C13	0.0549 (11)	0.0362 (9)	0.0361 (9)	0.0010 (8)	−0.0024 (8)	−0.0132 (7)
C14	0.0569 (11)	0.0282 (9)	0.0351 (9)	−0.0008 (8)	−0.0020 (8)	−0.0100 (7)

Geometric parameters (Å, º)

O1—C3	1.212 (2)	C4—H4A	0.9700
O2—C3	1.369 (2)	C4—H4B	0.9700
O2—C1	1.4596 (19)	C4—H4A'	0.9650
O3—C14	1.248 (2)	C4—H4B'	0.9605
O4—C14	1.301 (2)	C5—H5A	0.9700
C1—C7A	1.503 (2)	C5—H5B	0.9700
C1—C8	1.535 (2)	C6—H6A	0.9700
C3—C3A	1.472 (2)	C6—H6B	0.9700
C3A—C7A	1.331 (2)	C5'—H5'A	0.9700
C3A—C4	1.504 (2)	C5'—H5'B	0.9700
C4—C5	1.497 (15)	C6'—H6'A	0.9700
C4—C5'	1.545 (8)	C6'—H6'B	0.9700
C5—C6	1.533 (19)	C7—H7A	0.9700
C6—C7	1.617 (10)	C7—H7B	0.9700
C5'—C6'	1.527 (11)	C7—H7A'	0.9601
C6'—C7	1.523 (5)	C7—H7B'	0.9626
C7—C7A	1.492 (2)	C8—H8	0.9800
C8—C13	1.532 (2)	C9—H9	0.9800
C8—C9	1.552 (2)	C10—H10A	0.9700
C9—C14	1.512 (2)	C10—H10B	0.9700
C9—C10	1.549 (2)	C11—H11A	0.9700
C10—C11	1.530 (3)	C11—H11B	0.9700
C11—C12	1.527 (3)	C12—H12A	0.9700
C12—C13	1.530 (2)	C12—H12B	0.9700
O3—H3	0.8200	C13—H13A	0.9700
O4—H4	0.8200	C13—H13B	0.9700
C1—H1	0.9800
C3—O2—C1	109.39 (12)	C6—C5—H5B	109.5
O2—C1—C7A	103.45 (12)	H5A—C5—H5B	108.1
O2—C1—C8	110.41 (12)	C5—C6—H6A	110.0
C7A—C1—C8	115.43 (13)	C7—C6—H6A	110.0
O1—C3—O2	121.03 (16)	C5—C6—H6B	110.0
O1—C3—C3A	130.20 (17)	C7—C6—H6B	110.0
O2—C3—C3A	108.77 (14)	H6A—C6—H6B	108.4
C7A—C3A—C3	108.09 (15)	C6'—C5'—H5'A	109.3
C7A—C3A—C4	124.73 (15)	C4—C5'—H5'A	109.3
C3—C3A—C4	127.18 (15)	C6'—C5'—H5'B	109.3
C5—C4—C3A	111.4 (6)	C4—C5'—H5'B	109.3
C5—C4—C5'	23.5 (4)	H5'A—C5'—H5'B	107.9
C3A—C4—C5'	109.0 (3)	C7—C6'—H6'A	109.6
C4—C5—C6	110.8 (10)	C5'—C6'—H6'A	109.6
C5—C6—C7	108.6 (10)	C7—C6'—H6'B	109.6
C6'—C5'—C4	111.8 (5)	C5'—C6'—H6'B	109.6
C7—C6'—C5'	110.3 (5)	H6'A—C6'—H6'B	108.1
C7A—C7—C6'	110.2 (2)	C7A—C7—H7A	110.3
C7A—C7—C6	107.2 (3)	C6'—C7—H7A	76.8
C6'—C7—C6	35.3 (3)	C6—C7—H7A	110.3
C3A—C7A—C7	124.51 (16)	C7A—C7—H7B	110.3
C3A—C7A—C1	110.29 (14)	C6'—C7—H7B	133.9
C7—C7A—C1	125.19 (15)	C6—C7—H7B	110.3
C13—C8—C1	113.43 (13)	H7A—C7—H7B	108.5
C13—C8—C9	112.93 (13)	C7A—C7—H7A'	110.1
C1—C8—C9	112.55 (13)	C6'—C7—H7A'	110.3
C14—C9—C10	111.48 (14)	C6—C7—H7A'	137.4
C14—C9—C8	113.31 (14)	H7A—C7—H7A'	36.5
C10—C9—C8	110.30 (14)	H7B—C7—H7A'	75.0
C11—C10—C9	113.83 (15)	C7A—C7—H7B'	109.3
C12—C11—C10	111.12 (15)	C6'—C7—H7B'	109.1
C11—C12—C13	111.34 (15)	C6—C7—H7B'	77.6
C12—C13—C8	111.30 (14)	H7A—C7—H7B'	134.7
O3—C14—O4	122.43 (16)	H7B—C7—H7B'	35.2
O3—C14—C9	122.41 (15)	H7A'—C7—H7B'	108.0
O4—C14—C9	115.16 (15)	C13—C8—H8	105.7
C14—O3—H3	109.5	C1—C8—H8	105.7
C14—O4—H4	109.5	C9—C8—H8	105.7
O2—C1—H1	109.1	C14—C9—H9	107.1
C7A—C1—H1	109.1	C10—C9—H9	107.1
C8—C1—H1	109.1	C8—C9—H9	107.1
C5—C4—H4A	109.3	C11—C10—H10A	108.8
C3A—C4—H4A	109.3	C9—C10—H10A	108.8
C5'—C4—H4A	129.1	C11—C10—H10B	108.8
C5—C4—H4B	109.3	C9—C10—H10B	108.8
C3A—C4—H4B	109.3	H10A—C10—H10B	107.7
C5'—C4—H4B	89.2	C12—C11—H11A	109.4
H4A—C4—H4B	108.0	C10—C11—H11A	109.4
C5—C4—H4A'	126.9	C12—C11—H11B	109.4
C3A—C4—H4A'	110.0	C10—C11—H11B	109.4
C5'—C4—H4A'	110.3	H11A—C11—H11B	108.0
H4A—C4—H4A'	86.2	C11—C12—H12A	109.4
H4B—C4—H4A'	23.5	C13—C12—H12A	109.4
C5—C4—H4B'	87.7	C11—C12—H12B	109.4
C3A—C4—H4B'	109.8	C13—C12—H12B	109.4
C5'—C4—H4B'	109.9	H12A—C12—H12B	108.0
H4A—C4—H4B'	24.1	C12—C13—H13A	109.4
H4B—C4—H4B'	127.1	C8—C13—H13A	109.4
H4A'—C4—H4B'	107.9	C12—C13—H13B	109.4
C4—C5—H5A	109.5	C8—C13—H13B	109.4
C6—C5—H5A	109.5	H13A—C13—H13B	108.0
C4—C5—H5B	109.5
C3—O2—C1—C7A	−1.03 (15)	C6—C7—C7A—C3A	21.1 (6)
C3—O2—C1—C8	123.03 (14)	C6'—C7—C7A—C1	162.7 (4)
C1—O2—C3—O1	−179.32 (15)	C6—C7—C7A—C1	−160.1 (5)
C1—O2—C3—C3A	0.96 (16)	O2—C1—C7A—C3A	0.74 (17)
O1—C3—C3A—C7A	179.84 (17)	C8—C1—C7A—C3A	−119.97 (15)
O2—C3—C3A—C7A	−0.48 (18)	O2—C1—C7A—C7	−178.19 (15)
O1—C3—C3A—C4	−0.2 (3)	C8—C1—C7A—C7	61.1 (2)
O2—C3—C3A—C4	179.52 (15)	O2—C1—C8—C13	−59.94 (17)
C7A—C3A—C4—C5	12.1 (6)	C7A—C1—C8—C13	56.91 (18)
C3—C3A—C4—C5	−167.9 (6)	O2—C1—C8—C9	69.83 (17)
C7A—C3A—C4—C5'	−12.8 (4)	C7A—C1—C8—C9	−173.32 (13)
C3—C3A—C4—C5'	167.2 (3)	C13—C8—C9—C14	74.98 (18)
C3A—C4—C5—C6	−44.4 (14)	C1—C8—C9—C14	−55.04 (18)
C5'—C4—C5—C6	44.1 (17)	C13—C8—C9—C10	−50.79 (19)
C4—C5—C6—C7	65.8 (15)	C1—C8—C9—C10	179.19 (14)
C5—C4—C5'—C6'	−56 (2)	C14—C9—C10—C11	−76.23 (19)
C3A—C4—C5'—C6'	44.4 (7)	C8—C9—C10—C11	50.6 (2)
C4—C5'—C6'—C7	−64.0 (9)	C9—C10—C11—C12	−53.7 (2)
C5'—C6'—C7—C7A	47.0 (7)	C10—C11—C12—C13	55.9 (2)
C5'—C6'—C7—C6	−44.6 (6)	C11—C12—C13—C8	−56.7 (2)
C5—C6—C7—C7A	−51.4 (12)	C1—C8—C13—C12	−175.74 (13)
C5—C6—C7—C6'	49.3 (9)	C9—C8—C13—C12	54.69 (19)
C3—C3A—C7A—C7	178.75 (16)	C10—C9—C14—O3	53.4 (2)
C4—C3A—C7A—C7	−1.2 (3)	C8—C9—C14—O3	−71.7 (2)
C3—C3A—C7A—C1	−0.20 (18)	C10—C9—C14—O4	−126.31 (16)
C4—C3A—C7A—C1	179.80 (15)	C8—C9—C14—O4	108.56 (17)
C6'—C7—C7A—C3A	−16.1 (4)

(II) (±)-cis-2-(3-Oxo-1,3,4,5,6,7-hexahydroisobenzofuran-1-yl)- cyclohexanecarboxylic acid

Crystal data

C15H20O4	Dx = 1.240 Mg m^−3
Mr = 264.32	Melting point = 472–476 K
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 11.372 (7) Å	Cell parameters from 41 reflections
b = 10.467 (9) Å	θ = 1.7–16.7°
c = 11.901 (16) Å	µ = 0.09 mm^−1
β = 91.11 (7)°	T = 293 K
V = 1416 (2) Å^3	Rectangular prism, colorless
Z = 4	0.50 × 0.30 × 0.25 mm
F(000) = 568

Data collection

Siemens P4 diffractometer	Rint = 0.025
Radiation source: normal-focus sealed tube	θmax = 25.0°, θmin = 2.6°
Graphite monochromator	h = −13→13
2θ/θ scans	k = 0→12
3242 measured reflections	l = 0→14
2498 independent reflections	3 standard reflections every 97 reflections
1151 reflections with I > 2σ(I)	intensity decay: variation < 3.0%

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)] = 0.065	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.237	H-atom parameters constrained
S = 1.09	w = 1/[σ^2(Fo^2) + (0.0941P)^2 + 0.6553P] where P = (Fo^2 + 2Fc^2)/3
2498 reflections	(Δ/σ)max < 0.001
175 parameters	Δρmax = 0.42 e Å^−3
0 restraints	Δρmin = −0.32 e Å^−3

Special details

Experimental. Crystal mounted on glass fiber using epoxy resin

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
O1	0.5226 (3)	0.7519 (4)	0.5555 (3)	0.1007 (11)
O2	0.6491 (2)	0.6445 (3)	0.4484 (2)	0.0717 (8)
O3	0.8875 (2)	0.4831 (3)	0.4112 (3)	0.0849 (9)
O4	0.9972 (3)	0.6557 (3)	0.4385 (3)	0.0884 (10)
C1	0.6439 (3)	0.5640 (4)	0.3489 (3)	0.0614 (10)
C3	0.5380 (3)	0.6856 (4)	0.4745 (3)	0.0701 (11)
C3A	0.4564 (3)	0.6343 (4)	0.3910 (3)	0.0637 (10)
C4	0.3269 (3)	0.6592 (5)	0.3855 (4)	0.0858 (13)
C5	0.2799 (5)	0.6207 (9)	0.2736 (6)	0.151 (3)
C6	0.3251 (5)	0.5033 (6)	0.2291 (6)	0.129 (2)
C7A	0.5148 (3)	0.5630 (4)	0.3177 (3)	0.0632 (10)
C7	0.4592 (4)	0.4927 (4)	0.2213 (4)	0.0815 (13)
C8	0.7280 (3)	0.6140 (4)	0.2594 (3)	0.0640 (10)
C9	0.8393 (3)	0.6770 (4)	0.3083 (3)	0.0619 (10)
C10	0.9204 (4)	0.7220 (4)	0.2126 (4)	0.0837 (13)
C11	0.9509 (4)	0.6126 (5)	0.1344 (4)	0.1010 (16)
C12	0.8406 (5)	0.5556 (6)	0.0836 (4)	0.1101 (18)
C13	0.7563 (4)	0.5088 (4)	0.1740 (3)	0.0832 (13)
C14	0.9083 (3)	0.5958 (4)	0.3896 (3)	0.0645 (10)
H1	0.6678	0.4772	0.3701	0.074*
H4	1.044 (3)	0.593 (4)	0.498 (3)	0.080*
H4A	0.2881	0.6109	0.4437	0.103*
H4B	0.3118	0.7493	0.3979	0.103*
H5A	0.1951	0.6131	0.2781	0.181*
H5B	0.2962	0.6886	0.2207	0.181*
H6A	0.2913	0.4911	0.1544	0.155*
H6B	0.2976	0.4337	0.2756	0.155*
H7A	0.4826	0.4036	0.2237	0.098*
H7B	0.4849	0.5289	0.1509	0.098*
H8A	0.6852	0.6807	0.2177	0.077*
H9A	0.8146	0.7535	0.3490	0.074*
H10A	0.8813	0.7890	0.1698	0.100*
H10B	0.9923	0.7573	0.2451	0.100*
H11A	1.0007	0.6439	0.0751	0.121*
H11B	0.9941	0.5475	0.1760	0.121*
H12A	0.8614	0.4844	0.0357	0.132*
H12B	0.8011	0.6192	0.0372	0.132*
H13A	0.7915	0.4367	0.2133	0.100*
H13B	0.6838	0.4797	0.1382	0.100*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.094 (2)	0.119 (3)	0.089 (2)	−0.0041 (19)	0.0186 (17)	−0.031 (2)
O2	0.0554 (14)	0.097 (2)	0.0625 (15)	−0.0054 (14)	−0.0015 (12)	−0.0066 (14)
O3	0.0748 (19)	0.0740 (19)	0.105 (2)	0.0019 (16)	−0.0281 (16)	0.0185 (17)
O4	0.0767 (19)	0.0802 (19)	0.107 (2)	−0.0083 (16)	−0.0293 (17)	0.0167 (17)
C1	0.060 (2)	0.068 (2)	0.057 (2)	0.0058 (19)	−0.0041 (16)	−0.0042 (18)
C3	0.064 (2)	0.074 (3)	0.072 (2)	−0.003 (2)	0.007 (2)	−0.002 (2)
C3A	0.054 (2)	0.064 (2)	0.073 (2)	−0.0038 (19)	−0.0023 (18)	0.008 (2)
C4	0.054 (2)	0.101 (3)	0.102 (3)	0.000 (2)	−0.002 (2)	0.023 (3)
C5	0.067 (3)	0.210 (8)	0.175 (6)	0.019 (4)	−0.041 (4)	−0.019 (6)
C6	0.091 (4)	0.129 (5)	0.165 (6)	−0.019 (4)	−0.055 (4)	−0.023 (4)
C7A	0.060 (2)	0.059 (2)	0.070 (2)	−0.0066 (19)	−0.0123 (18)	0.0085 (19)
C7	0.086 (3)	0.071 (3)	0.086 (3)	−0.012 (2)	−0.025 (2)	−0.003 (2)
C8	0.059 (2)	0.076 (2)	0.057 (2)	0.0153 (19)	−0.0013 (16)	0.0016 (19)
C9	0.057 (2)	0.066 (2)	0.062 (2)	0.0115 (18)	0.0054 (17)	0.0067 (18)
C10	0.074 (3)	0.090 (3)	0.087 (3)	0.018 (2)	0.015 (2)	0.023 (2)
C11	0.089 (3)	0.130 (4)	0.085 (3)	0.033 (3)	0.027 (3)	0.022 (3)
C12	0.122 (4)	0.144 (5)	0.064 (3)	0.041 (4)	0.011 (3)	−0.010 (3)
C13	0.086 (3)	0.092 (3)	0.072 (3)	0.020 (3)	−0.004 (2)	−0.017 (2)
C14	0.054 (2)	0.074 (3)	0.065 (2)	0.011 (2)	0.0003 (18)	0.003 (2)

Geometric parameters (Å, º)

O1—C3	1.203 (5)	O4—H4	1.09 (4)
O2—C3	1.375 (5)	C1—H1	0.9800
O2—C1	1.454 (4)	C4—H4A	0.9700
O3—C14	1.231 (5)	C4—H4B	0.9700
O4—C14	1.315 (5)	C5—H5A	0.9700
C1—C7A	1.508 (5)	C5—H5B	0.9700
C1—C8	1.537 (5)	C6—H6A	0.9700
C3—C3A	1.449 (6)	C6—H6B	0.9700
C3A—C7A	1.334 (5)	C7—H7A	0.9700
C3A—C4	1.496 (5)	C7—H7B	0.9700
C4—C5	1.482 (8)	C8—H8A	0.9800
C5—C6	1.436 (8)	C9—H9A	0.9800
C6—C7	1.534 (7)	C10—H10A	0.9700
C7A—C7	1.493 (5)	C10—H10B	0.9700
C8—C9	1.532 (5)	C11—H11A	0.9700
C8—C13	1.536 (5)	C11—H11B	0.9700
C9—C14	1.498 (5)	C12—H12A	0.9700
C9—C10	1.552 (5)	C12—H12B	0.9700
C10—C11	1.520 (6)	C13—H13A	0.9700
C11—C12	1.506 (7)	C13—H13B	0.9700
C12—C13	1.535 (6)
C3—O2—C1	110.0 (3)	C4—C5—H5A	108.3
O2—C1—C7A	103.2 (3)	C6—C5—H5B	108.3
O2—C1—C8	110.6 (3)	C4—C5—H5B	108.3
C7A—C1—C8	116.6 (3)	H5A—C5—H5B	107.4
O1—C3—O2	120.7 (4)	C5—C6—H6A	108.1
O1—C3—C3A	131.4 (4)	C7—C6—H6A	108.1
O2—C3—C3A	107.9 (3)	C5—C6—H6B	108.1
C7A—C3A—C3	109.6 (3)	C7—C6—H6B	108.1
C7A—C3A—C4	124.8 (4)	H6A—C6—H6B	107.3
C3—C3A—C4	125.6 (4)	C7A—C7—H7A	109.9
C5—C4—C3A	109.2 (4)	C6—C7—H7A	109.9
C6—C5—C4	116.0 (5)	C7A—C7—H7B	109.9
C5—C6—C7	116.6 (5)	C6—C7—H7B	109.9
C3A—C7A—C7	124.7 (4)	H7A—C7—H7B	108.3
C3A—C7A—C1	109.3 (3)	C9—C8—H8A	106.5
C7—C7A—C1	126.0 (4)	C13—C8—H8A	106.5
C7A—C7—C6	108.9 (4)	C1—C8—H8A	106.5
C9—C8—C13	112.2 (3)	C14—C9—H9A	107.2
C9—C8—C1	113.8 (3)	C8—C9—H9A	107.2
C13—C8—C1	110.8 (3)	C10—C9—H9A	107.2
C14—C9—C8	114.8 (3)	C11—C10—H10A	109.3
C14—C9—C10	109.6 (3)	C9—C10—H10A	109.3
C8—C9—C10	110.5 (3)	C11—C10—H10B	109.3
C11—C10—C9	111.5 (4)	C9—C10—H10B	109.3
C12—C11—C10	110.3 (4)	H10A—C10—H10B	108.0
C11—C12—C13	111.8 (4)	C12—C11—H11A	109.6
C12—C13—C8	112.2 (4)	C10—C11—H11A	109.6
O3—C14—O4	120.9 (4)	C12—C11—H11B	109.6
O3—C14—C9	125.3 (4)	C10—C11—H11B	109.6
O4—C14—C9	113.8 (4)	H11A—C11—H11B	108.1
C14—O4—H4	111 (2)	C11—C12—H12A	109.2
O2—C1—H1	108.7	C13—C12—H12A	109.2
C7A—C1—H1	108.7	C11—C12—H12B	109.2
C8—C1—H1	108.7	C13—C12—H12B	109.2
C5—C4—H4A	109.8	H12A—C12—H12B	107.9
C3A—C4—H4A	109.8	C12—C13—H13A	109.2
C5—C4—H4B	109.8	C8—C13—H13A	109.2
C3A—C4—H4B	109.8	C12—C13—H13B	109.2
H4A—C4—H4B	108.3	C8—C13—H13B	109.2
C6—C5—H5A	108.3	H13A—C13—H13B	107.9
C3—O2—C1—C7A	0.6 (4)	C1—C7A—C7—C6	172.6 (4)
C3—O2—C1—C8	125.9 (3)	C5—C6—C7—C7A	34.1 (7)
C1—O2—C3—O1	178.8 (4)	O2—C1—C8—C9	32.7 (4)
C1—O2—C3—C3A	−0.9 (4)	C7A—C1—C8—C9	150.1 (3)
O1—C3—C3A—C7A	−178.7 (4)	O2—C1—C8—C13	160.2 (3)
O2—C3—C3A—C7A	0.9 (4)	C7A—C1—C8—C13	−82.4 (4)
O1—C3—C3A—C4	2.6 (7)	C13—C8—C9—C14	−72.6 (4)
O2—C3—C3A—C4	−177.8 (4)	C1—C8—C9—C14	54.2 (4)
C7A—C3A—C4—C5	−13.9 (7)	C13—C8—C9—C10	51.9 (4)
C3—C3A—C4—C5	164.7 (5)	C1—C8—C9—C10	178.7 (3)
C3A—C4—C5—C6	41.4 (8)	C14—C9—C10—C11	71.6 (5)
C4—C5—C6—C7	−54.8 (9)	C8—C9—C10—C11	−55.9 (4)
C3—C3A—C7A—C7	178.6 (4)	C9—C10—C11—C12	58.5 (5)
C4—C3A—C7A—C7	−2.6 (6)	C10—C11—C12—C13	−57.2 (6)
C3—C3A—C7A—C1	−0.6 (4)	C11—C12—C13—C8	53.9 (5)
C4—C3A—C7A—C1	178.2 (4)	C9—C8—C13—C12	−51.4 (5)
O2—C1—C7A—C3A	0.0 (4)	C1—C8—C13—C12	−179.8 (3)
C8—C1—C7A—C3A	−121.3 (4)	C8—C9—C14—O3	6.3 (5)
O2—C1—C7A—C7	−179.2 (3)	C10—C9—C14—O3	−118.8 (4)
C8—C1—C7A—C7	59.5 (5)	C8—C9—C14—O4	−173.9 (3)
C3A—C7A—C7—C6	−6.5 (6)	C10—C9—C14—O4	61.1 (4)