2-Hydro­xy­cyclo­hexene-1-carboxyl­ic acid: the enol isomer of 2-oxo­cyclo­hexane-1-carboxyl­ic acid

There are four independent mol­ecules in the asymmetric unit of the title compound, C₇H₁₀O₃, and two of the molecules are disordered. Molecules form two independent O—H...O hydrogen-bonded dimers, through the carboxyl groups, with O...O distances of 2.669 (3), 2.661 (3), 2.653 (3) and 2.654 (3) Å. Each hydrogen-bonded dimer contains a disordered mol­ecule.

Key indicators

• Single-crystal X-ray study
• T = 150 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.046
• wR factor = 0.118
• Data-to-parameter ratio = 8.1

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

General Notes



REFLT_03
         From the CIF: _diffrn_reflns_theta_max           27.46
         From the CIF: _reflns_number_total               3220
         Count of symmetry unique reflns         3236
         Completeness (_total/calc)             99.51%
         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
          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.

---

Computing details

Data collection: COLLECT (Nonius BV, 1997-2002); cell refinement: DENZO–SMN (Otwinowski & Minor, 1997); data reduction: DENZO–SMN; program(s) used to solve structure: SHELXTL (Sheldrick, 2001); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

2-Hydroxycyclohexene-1-carboxylic acid

Crystal data

C7H10O3	F(000) = 1216
Mr = 142.15	Dx = 1.336 Mg m^−3
Monoclinic, Cc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2yc	Cell parameters from 2659 reflections
a = 11.1360 (4) Å	θ = 2.6–27.5°
b = 11.1049 (3) Å	µ = 0.10 mm^−1
c = 22.8774 (9) Å	T = 150 K
β = 91.9072 (12)°	Block, colourless
V = 2827.55 (17) Å^3	0.40 × 0.35 × 0.30 mm
Z = 16

Data collection

Nonius KappaCCD diffractometer	2554 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.039
Graphite monochromator	θmax = 27.5°, θmin = 2.6°
Detector resolution: 9 pixels mm^-1	h = −14→14
φ scans and ω scans with κ offsets	k = −14→14
8426 measured reflections	l = −29→29
3220 independent reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.046	H-atom parameters constrained
wR(F^2) = 0.118	w = 1/[σ^2(Fo^2) + (0.052P)^2 + 1.6672P] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max < 0.001
3220 reflections	Δρmax = 0.41 e Å^−3
400 parameters	Δρmin = −0.20 e Å^−3
32 restraints	Extinction correction: SHELXTL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0047 (12)

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	Occ. (<1)
O1A	0.5025 (2)	0.4443 (2)	0.99826 (11)	0.0384 (6)
H1A	0.4503	0.4572	0.9716	0.058*
O2A	0.3979 (2)	0.4165 (2)	0.89731 (11)	0.0403 (6)
O3A	0.4585 (3)	0.2646 (2)	0.84107 (11)	0.0443 (7)
H3A	0.4025	0.2917	0.8194	0.066*
C1A	0.5592 (3)	0.2919 (3)	0.93167 (14)	0.0327 (7)
C2A	0.5721 (3)	0.3514 (3)	0.98299 (14)	0.0319 (7)
C3A	0.6637 (4)	0.3198 (3)	1.02951 (16)	0.0412 (8)
H3AA	0.7046	0.3944	1.0430	0.049*
H3AB	0.6221	0.2853	1.0633	0.049*
C4A	0.7558 (4)	0.2324 (5)	1.01036 (19)	0.0592 (12)
H4AA	0.8175	0.2757	0.9884	0.071*
H4AB	0.7960	0.1955	1.0452	0.071*
C5A	0.7025 (4)	0.1365 (4)	0.9731 (2)	0.0618 (12)
H5AA	0.6443	0.0904	0.9960	0.074*
H5AB	0.7668	0.0804	0.9617	0.074*
C6A	0.6381 (4)	0.1853 (4)	0.91744 (17)	0.0433 (9)
H6AA	0.6984	0.2102	0.8890	0.052*
H6AB	0.5881	0.1208	0.8993	0.052*
C7A	0.4671 (3)	0.3288 (3)	0.88942 (14)	0.0351 (8)
O1B	0.2544 (2)	−0.2838 (2)	0.66286 (11)	0.0400 (6)
H1B	0.2419	−0.2345	0.6898	0.060*
O2B	0.2888 (2)	−0.1846 (2)	0.76381 (11)	0.0384 (6)
O3B	0.4427 (2)	−0.2498 (3)	0.82081 (11)	0.0449 (7)
H3B	0.4164	−0.1956	0.8425	0.067*
C1B	0.4111 (3)	−0.3451 (3)	0.73005 (14)	0.0328 (7)
C2B	0.3481 (3)	−0.3553 (3)	0.67850 (15)	0.0315 (7)
C3B	0.3760 (4)	−0.4448 (3)	0.63269 (15)	0.0396 (8)
H3BA	0.4086	−0.4020	0.5987	0.048*
H3BB	0.3006	−0.4850	0.6194	0.048*
C4B	0.4649 (4)	−0.5396 (4)	0.65305 (18)	0.0563 (11)
H4BA	0.4229	−0.6017	0.6757	0.068*
H4BB	0.4992	−0.5792	0.6186	0.068*
C5B	0.5633 (4)	−0.4871 (4)	0.6898 (2)	0.0577 (11)
H5BA	0.6074	−0.4275	0.6665	0.069*
H5BB	0.6204	−0.5517	0.7017	0.069*
C6B	0.5172 (4)	−0.4254 (3)	0.74483 (17)	0.0412 (9)
H6BA	0.4933	−0.4875	0.7732	0.049*
H6BB	0.5826	−0.3768	0.7633	0.049*
C7B	0.3754 (3)	−0.2552 (3)	0.77191 (14)	0.0343 (8)
O1C	0.1713 (2)	0.3068 (2)	0.66833 (11)	0.0423 (6)
H1C	0.2215	0.2906	0.6955	0.063*
O2C	0.2761 (2)	0.3325 (2)	0.76997 (11)	0.0384 (6)
O3C	0.2192 (3)	0.4868 (2)	0.82564 (11)	0.0443 (7)
H3C	0.2743	0.4591	0.8477	0.066*
C1C	0.1165 (3)	0.4595 (3)	0.73599 (14)	0.0317 (7)
C2C	0.1048 (3)	0.4018 (3)	0.68371 (14)	0.0337 (7)
C3C	0.0160 (4)	0.4388 (3)	0.63633 (17)	0.0438 (9)
H3CA	−0.0520	0.3813	0.6351	0.053*	0.762 (7)
H3CB	0.0550	0.4354	0.5981	0.053*	0.762 (7)
C3C*	0.0160 (4)	0.4388 (3)	0.63633 (17)	0.0438 (9)	0.00
H3CC	−0.0202	0.3655	0.6185	0.053*	0.238 (7)
H3CD	0.0593	0.4817	0.6055	0.053*	0.238 (7)
C4C	−0.0320 (5)	0.5663 (4)	0.6461 (2)	0.0442 (13)	0.762 (7)
H4CA	0.0314	0.6260	0.6380	0.053*	0.762 (7)
H4CB	−0.1013	0.5817	0.6190	0.053*	0.762 (7)
C5C	−0.0709 (4)	0.5801 (6)	0.7092 (2)	0.0461 (15)	0.762 (7)
H5CA	−0.1068	0.6607	0.7147	0.055*	0.762 (7)
H5CB	−0.1323	0.5187	0.7178	0.055*	0.762 (7)
C4C*	−0.0847 (9)	0.5200 (14)	0.6577 (7)	0.0439 (17)	0.238 (7)
H4CC	−0.1286	0.5574	0.6240	0.053*	0.238 (7)
H4CD	−0.1423	0.4725	0.6803	0.053*	0.238 (7)
C5C*	−0.0255 (17)	0.6168 (12)	0.6964 (5)	0.0454 (19)	0.238 (7)
H5CC	0.0336	0.6616	0.6733	0.054*	0.238 (7)
H5CD	−0.0876	0.6747	0.7085	0.054*	0.238 (7)
C6C	0.0380 (4)	0.5647 (3)	0.75087 (16)	0.0388 (9)
H6CA	0.0867	0.6392	0.7503	0.047*	0.762 (7)
H6CB	0.0097	0.5540	0.7911	0.047*	0.762 (7)
C6C*	0.0380 (4)	0.5647 (3)	0.75087 (16)	0.0388 (9)	0.00
H6CC	0.0878	0.6280	0.7701	0.047*	0.238 (7)
H6CD	−0.0228	0.5383	0.7788	0.047*	0.238 (7)
C7C	0.2094 (3)	0.4203 (3)	0.77745 (14)	0.0333 (7)
O1D	0.4100 (2)	0.0251 (2)	0.99417 (11)	0.0418 (6)
H1D	0.4245	−0.0236	0.9672	0.063*
O2D	0.3796 (2)	−0.0729 (2)	0.89199 (11)	0.0405 (6)
O3D	0.2241 (3)	−0.0106 (2)	0.83577 (11)	0.0442 (7)
H3D	0.2506	−0.0647	0.8141	0.066*
C1D	0.2553 (3)	0.0860 (3)	0.92558 (14)	0.0308 (7)
C2D	0.3145 (3)	0.0939 (3)	0.97808 (14)	0.0326 (7)
C3D	0.2811 (4)	0.1792 (4)	1.02524 (17)	0.0436 (9)
H3DA	0.3395	0.2464	1.0271	0.052*	0.661 (6)
H3DB	0.2850	0.1370	1.0634	0.052*	0.661 (6)
C3D*	0.2811 (4)	0.1792 (4)	1.02524 (17)	0.0436 (9)	0.00
H3DC	0.3553	0.2128	1.0439	0.052*	0.339 (6)
H3DD	0.2379	0.1345	1.0555	0.052*	0.339 (6)
C4D	0.1529 (4)	0.2304 (5)	1.0141 (2)	0.0426 (14)	0.661 (6)
H4DA	0.0926	0.1670	1.0212	0.051*	0.661 (6)
H4DB	0.1388	0.2978	1.0414	0.051*	0.661 (6)
C5D	0.1395 (6)	0.2746 (5)	0.9512 (2)	0.0419 (15)	0.661 (6)
H5DA	0.2033	0.3339	0.9431	0.050*	0.661 (6)
H5DB	0.0606	0.3143	0.9448	0.050*	0.661 (6)
C5D*	0.1008 (8)	0.2264 (11)	0.9649 (3)	0.0412 (17)	0.339 (6)
H5DC	0.0415	0.2889	0.9529	0.049*	0.339 (6)
H5DD	0.0590	0.1655	0.9884	0.049*	0.339 (6)
C4D*	0.2010 (9)	0.2840 (7)	1.0023 (5)	0.0419 (17)	0.339 (6)
H4DC	0.1672	0.3291	1.0353	0.050*	0.339 (6)
H4DD	0.2482	0.3404	0.9786	0.050*	0.339 (6)
C6D	0.1496 (3)	0.1660 (3)	0.91009 (16)	0.0378 (8)
H6DA	0.0749	0.1179	0.9115	0.045*	0.661 (6)
H6DB	0.1571	0.1953	0.8695	0.045*	0.661 (6)
C6D*	0.1496 (3)	0.1660 (3)	0.91009 (16)	0.0378 (8)	0.00
H6DC	0.0852	0.1174	0.8907	0.045*	0.339 (6)
H6DD	0.1745	0.2287	0.8822	0.045*	0.339 (6)
C7D	0.2915 (3)	−0.0040 (3)	0.88395 (14)	0.0332 (7)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1A	0.0465 (14)	0.0384 (13)	0.0299 (12)	0.0081 (12)	−0.0028 (10)	−0.0049 (10)
O2A	0.0443 (15)	0.0430 (14)	0.0330 (13)	0.0133 (13)	−0.0054 (11)	−0.0069 (11)
O3A	0.0492 (16)	0.0508 (15)	0.0322 (14)	0.0160 (13)	−0.0080 (11)	−0.0128 (11)
C1A	0.0352 (18)	0.0354 (17)	0.0274 (16)	0.0049 (15)	0.0000 (14)	−0.0001 (13)
C2A	0.0325 (18)	0.0316 (16)	0.0315 (17)	−0.0050 (15)	0.0020 (14)	0.0007 (13)
C3A	0.048 (2)	0.0455 (19)	0.0297 (18)	−0.0004 (18)	−0.0046 (15)	0.0029 (15)
C4A	0.052 (3)	0.078 (3)	0.048 (2)	0.019 (2)	−0.0076 (19)	0.001 (2)
C5A	0.059 (3)	0.058 (3)	0.067 (3)	0.025 (2)	−0.016 (2)	−0.007 (2)
C6A	0.040 (2)	0.047 (2)	0.043 (2)	0.0077 (18)	−0.0030 (17)	−0.0047 (17)
C7A	0.040 (2)	0.0352 (17)	0.0304 (16)	0.0039 (16)	0.0004 (14)	−0.0035 (14)
O1B	0.0408 (14)	0.0489 (14)	0.0298 (11)	0.0114 (12)	−0.0053 (10)	−0.0009 (10)
O2B	0.0404 (15)	0.0430 (13)	0.0314 (13)	0.0129 (12)	−0.0073 (10)	−0.0044 (10)
O3B	0.0463 (15)	0.0552 (16)	0.0324 (13)	0.0199 (13)	−0.0102 (11)	−0.0074 (11)
C1B	0.0363 (19)	0.0343 (16)	0.0276 (16)	0.0062 (15)	0.0004 (14)	0.0006 (13)
C2B	0.0325 (18)	0.0322 (16)	0.0299 (16)	0.0008 (15)	0.0014 (13)	0.0018 (13)
C3B	0.044 (2)	0.0458 (19)	0.0294 (17)	0.0019 (17)	0.0025 (15)	−0.0026 (15)
C4B	0.076 (3)	0.053 (2)	0.041 (2)	0.021 (2)	0.000 (2)	−0.0079 (18)
C5B	0.058 (3)	0.055 (2)	0.060 (2)	0.022 (2)	−0.008 (2)	−0.015 (2)
C6B	0.044 (2)	0.040 (2)	0.039 (2)	0.0116 (18)	−0.0068 (16)	−0.0019 (16)
C7B	0.0353 (19)	0.0372 (17)	0.0300 (17)	0.0014 (16)	−0.0034 (14)	0.0017 (13)
O1C	0.0465 (15)	0.0428 (14)	0.0371 (13)	0.0115 (12)	−0.0081 (11)	−0.0127 (11)
O2C	0.0445 (14)	0.0380 (13)	0.0321 (13)	0.0119 (13)	−0.0069 (11)	−0.0079 (11)
O3C	0.0568 (18)	0.0471 (14)	0.0282 (12)	0.0202 (13)	−0.0109 (11)	−0.0106 (11)
C1C	0.0347 (18)	0.0301 (16)	0.0303 (17)	0.0023 (15)	0.0002 (14)	−0.0024 (13)
C2C	0.0346 (19)	0.0356 (17)	0.0308 (16)	0.0026 (15)	−0.0003 (14)	−0.0024 (14)
C3C	0.044 (2)	0.051 (2)	0.0354 (19)	0.0043 (18)	−0.0107 (16)	−0.0040 (16)
C3C*	0.044 (2)	0.051 (2)	0.0354 (19)	0.0043 (18)	−0.0107 (16)	−0.0040 (16)
C4C	0.047 (3)	0.044 (3)	0.040 (3)	0.007 (2)	−0.012 (2)	−0.002 (2)
C5C	0.045 (3)	0.042 (3)	0.051 (3)	0.016 (3)	−0.010 (2)	−0.007 (2)
C4C*	0.046 (4)	0.045 (4)	0.040 (3)	0.007 (3)	−0.012 (3)	−0.002 (3)
C5C*	0.044 (4)	0.041 (4)	0.050 (3)	0.015 (3)	−0.010 (3)	−0.006 (3)
C6C	0.038 (2)	0.0384 (19)	0.039 (2)	0.0094 (17)	−0.0049 (16)	−0.0032 (15)
C6C*	0.038 (2)	0.0384 (19)	0.039 (2)	0.0094 (17)	−0.0049 (16)	−0.0032 (15)
C7C	0.0389 (19)	0.0335 (16)	0.0275 (16)	0.0032 (16)	0.0024 (14)	−0.0013 (13)
O1D	0.0423 (14)	0.0446 (14)	0.0377 (14)	0.0116 (12)	−0.0112 (11)	−0.0059 (11)
O2D	0.0375 (15)	0.0477 (14)	0.0359 (14)	0.0126 (13)	−0.0064 (11)	−0.0068 (11)
O3D	0.0510 (16)	0.0511 (15)	0.0296 (13)	0.0181 (13)	−0.0120 (11)	−0.0099 (11)
C1D	0.0315 (17)	0.0321 (16)	0.0286 (16)	0.0010 (15)	−0.0019 (13)	−0.0017 (13)
C2D	0.0336 (19)	0.0332 (16)	0.0305 (17)	0.0029 (14)	−0.0040 (14)	0.0006 (13)
C3D	0.047 (2)	0.046 (2)	0.0374 (19)	0.0060 (18)	−0.0064 (16)	−0.0092 (16)
C3D*	0.047 (2)	0.046 (2)	0.0374 (19)	0.0060 (18)	−0.0064 (16)	−0.0092 (16)
C4D	0.047 (4)	0.037 (3)	0.044 (3)	0.010 (3)	0.001 (3)	−0.009 (2)
C5D	0.044 (4)	0.034 (3)	0.047 (3)	0.014 (3)	−0.006 (3)	−0.006 (2)
C5D*	0.045 (4)	0.032 (4)	0.046 (4)	0.013 (3)	−0.006 (3)	−0.005 (3)
C4D*	0.047 (4)	0.035 (4)	0.044 (3)	0.010 (3)	0.001 (3)	−0.008 (3)
C6D	0.036 (2)	0.0425 (19)	0.0340 (18)	0.0085 (17)	−0.0039 (15)	−0.0030 (15)
C6D*	0.036 (2)	0.0425 (19)	0.0340 (18)	0.0085 (17)	−0.0039 (15)	−0.0030 (15)
C7D	0.0325 (18)	0.0389 (17)	0.0279 (16)	0.0054 (15)	−0.0030 (13)	−0.0027 (14)

Geometric parameters (Å, º)

O1A—C2A	1.344 (4)	C1C—C2C	1.359 (4)
O1A—H1A	0.8400	C1C—C7C	1.447 (5)
O2A—C7A	1.259 (4)	C1C—C6C	1.505 (5)
O3A—C7A	1.317 (4)	C2C—C3C	1.500 (5)
O3A—H3A	0.8400	C3C—C4C	1.533 (6)
C1A—C2A	1.350 (4)	C3C—H3CA	0.9900
C1A—C7A	1.445 (5)	C3C—H3CB	0.9900
C1A—C6A	1.516 (5)	C4C—C5C	1.528 (6)
C2A—C3A	1.491 (5)	C4C—H4CA	0.9900
C3A—C4A	1.489 (6)	C4C—H4CB	0.9900
C3A—H3AA	0.9900	C5C—C6C	1.527 (6)
C3A—H3AB	0.9900	C5C—H5CA	0.9900
C4A—C5A	1.476 (6)	C5C—H5CB	0.9900
C4A—H4AA	0.9900	C4C*—C5C*	1.528 (6)
C4A—H4AB	0.9900	C4C*—H4CC	0.9900
C5A—C6A	1.539 (6)	C4C*—H4CD	0.9900
C5A—H5AA	0.9900	C5C*—H5CC	0.9900
C5A—H5AB	0.9900	C5C*—H5CD	0.9900
C6A—H6AA	0.9900	C6C—H6CA	0.9900
C6A—H6AB	0.9900	C6C—H6CB	0.9900
O1B—C2B	1.349 (4)	O1D—C2D	1.350 (4)
O1B—H1B	0.8400	O1D—H1D	0.8400
O2B—C7B	1.251 (4)	O2D—C7D	1.253 (4)
O3B—C7B	1.327 (4)	O3D—C7D	1.314 (4)
O3B—H3B	0.8400	O3D—H3D	0.8400
C1B—C2B	1.357 (5)	C1D—C2D	1.353 (4)
C1B—C7B	1.448 (5)	C1D—C7D	1.448 (4)
C1B—C6B	1.511 (5)	C1D—C6D	1.507 (5)
C2B—C3B	1.485 (5)	C2D—C3D	1.492 (5)
C3B—C4B	1.508 (6)	C3D—C4D	1.550 (6)
C3B—H3BA	0.9900	C3D—H3DA	0.9900
C3B—H3BB	0.9900	C3D—H3DB	0.9900
C4B—C5B	1.479 (6)	C4D—C5D	1.524 (6)
C4B—H4BA	0.9900	C4D—H4DA	0.9900
C4B—H4BB	0.9900	C4D—H4DB	0.9900
C5B—C6B	1.536 (6)	C5D—C6D	1.536 (5)
C5B—H5BA	0.9900	C5D—H5DA	0.9900
C5B—H5BB	0.9900	C5D—H5DB	0.9900
C6B—H6BA	0.9900	C5D*—C4D*	1.524 (6)
C6B—H6BB	0.9900	C5D*—H5DC	0.9900
O1C—C2C	1.343 (4)	C5D*—H5DD	0.9900
O1C—H1C	0.8400	C4D*—H4DC	0.9900
O2C—C7C	1.241 (4)	C4D*—H4DD	0.9900
O3C—C7C	1.328 (4)	C6D—H6DA	0.9900
O3C—H3C	0.8400	C6D—H6DB	0.9900
C2A—O1A—H1A	109.5	O1C—C2C—C3C	112.4 (3)
C7A—O3A—H3A	109.5	C1C—C2C—C3C	123.3 (3)
C2A—C1A—C7A	119.7 (3)	C2C—C3C—C4C	111.8 (3)
C2A—C1A—C6A	121.5 (3)	C2C—C3C—H3CA	109.3
C7A—C1A—C6A	118.8 (3)	C4C—C3C—H3CA	109.3
O1A—C2A—C1A	123.7 (3)	C2C—C3C—H3CB	109.3
O1A—C2A—C3A	112.5 (3)	C4C—C3C—H3CB	109.3
C1A—C2A—C3A	123.8 (3)	H3CA—C3C—H3CB	107.9
C4A—C3A—C2A	113.9 (3)	C5C—C4C—C3C	110.0 (4)
C4A—C3A—H3AA	108.8	C5C—C4C—H4CA	109.7
C2A—C3A—H3AA	108.8	C3C—C4C—H4CA	109.7
C4A—C3A—H3AB	108.8	C5C—C4C—H4CB	109.7
C2A—C3A—H3AB	108.8	C3C—C4C—H4CB	109.7
H3AA—C3A—H3AB	107.7	H4CA—C4C—H4CB	108.2
C5A—C4A—C3A	111.8 (4)	C6C—C5C—C4C	109.5 (4)
C5A—C4A—H4AA	109.2	C6C—C5C—H5CA	109.8
C3A—C4A—H4AA	109.2	C4C—C5C—H5CA	109.8
C5A—C4A—H4AB	109.2	C6C—C5C—H5CB	109.8
C3A—C4A—H4AB	109.2	C4C—C5C—H5CB	109.8
H4AA—C4A—H4AB	107.9	H5CA—C5C—H5CB	108.2
C4A—C5A—C6A	113.1 (4)	C5C*—C4C*—H4CC	110.3
C4A—C5A—H5AA	109.0	C5C*—C4C*—H4CD	110.3
C6A—C5A—H5AA	109.0	H4CC—C4C*—H4CD	108.6
C4A—C5A—H5AB	109.0	C4C*—C5C*—H5CC	109.1
C6A—C5A—H5AB	109.0	C4C*—C5C*—H5CD	109.1
H5AA—C5A—H5AB	107.8	H5CC—C5C*—H5CD	107.8
C1A—C6A—C5A	110.8 (3)	C1C—C6C—C5C	113.7 (3)
C1A—C6A—H6AA	109.5	C1C—C6C—H6CA	108.8
C5A—C6A—H6AA	109.5	C5C—C6C—H6CA	108.8
C1A—C6A—H6AB	109.5	C1C—C6C—H6CB	108.8
C5A—C6A—H6AB	109.5	C5C—C6C—H6CB	108.8
H6AA—C6A—H6AB	108.1	H6CA—C6C—H6CB	107.7
O2A—C7A—O3A	120.8 (3)	O2C—C7C—O3C	121.2 (3)
O2A—C7A—C1A	123.2 (3)	O2C—C7C—C1C	124.3 (3)
O3A—C7A—C1A	116.0 (3)	O3C—C7C—C1C	114.5 (3)
C2B—O1B—H1B	109.5	C2D—O1D—H1D	109.5
C7B—O3B—H3B	109.5	C7D—O3D—H3D	109.5
C2B—C1B—C7B	119.2 (3)	C2D—C1D—C7D	119.4 (3)
C2B—C1B—C6B	121.6 (3)	C2D—C1D—C6D	121.6 (3)
C7B—C1B—C6B	119.3 (3)	C7D—C1D—C6D	119.0 (3)
O1B—C2B—C1B	123.7 (3)	O1D—C2D—C1D	124.2 (3)
O1B—C2B—C3B	112.6 (3)	O1D—C2D—C3D	112.0 (3)
C1B—C2B—C3B	123.7 (3)	C1D—C2D—C3D	123.8 (3)
C2B—C3B—C4B	113.6 (3)	C2D—C3D—C4D	111.4 (3)
C2B—C3B—H3BA	108.8	C2D—C3D—H3DA	109.4
C4B—C3B—H3BA	108.8	C4D—C3D—H3DA	109.4
C2B—C3B—H3BB	108.8	C2D—C3D—H3DB	109.4
C4B—C3B—H3BB	108.8	C4D—C3D—H3DB	109.4
H3BA—C3B—H3BB	107.7	H3DA—C3D—H3DB	108.0
C5B—C4B—C3B	111.6 (3)	C5D—C4D—C3D	109.5 (4)
C5B—C4B—H4BA	109.3	C5D—C4D—H4DA	109.8
C3B—C4B—H4BA	109.3	C3D—C4D—H4DA	109.8
C5B—C4B—H4BB	109.3	C5D—C4D—H4DB	109.8
C3B—C4B—H4BB	109.3	C3D—C4D—H4DB	109.8
H4BA—C4B—H4BB	108.0	H4DA—C4D—H4DB	108.2
C4B—C5B—C6B	112.3 (4)	C4D—C5D—C6D	108.6 (4)
C4B—C5B—H5BA	109.1	C4D—C5D—H5DA	110.0
C6B—C5B—H5BA	109.1	C6D—C5D—H5DA	110.0
C4B—C5B—H5BB	109.1	C4D—C5D—H5DB	110.0
C6B—C5B—H5BB	109.1	C6D—C5D—H5DB	110.0
H5BA—C5B—H5BB	107.9	H5DA—C5D—H5DB	108.4
C1B—C6B—C5B	111.1 (3)	C4D*—C5D*—H5DC	109.3
C1B—C6B—H6BA	109.4	C4D*—C5D*—H5DD	109.3
C5B—C6B—H6BA	109.4	H5DC—C5D*—H5DD	108.0
C1B—C6B—H6BB	109.4	C5D*—C4D*—H4DC	110.5
C5B—C6B—H6BB	109.4	C5D*—C4D*—H4DD	110.5
H6BA—C6B—H6BB	108.0	H4DC—C4D*—H4DD	108.7
O2B—C7B—O3B	120.5 (3)	C1D—C6D—C5D	113.0 (4)
O2B—C7B—C1B	124.1 (3)	C1D—C6D—H6DA	109.0
O3B—C7B—C1B	115.4 (3)	C5D—C6D—H6DA	109.0
C2C—O1C—H1C	109.5	C1D—C6D—H6DB	109.0
C7C—O3C—H3C	109.5	C5D—C6D—H6DB	109.0
C2C—C1C—C7C	118.7 (3)	H6DA—C6D—H6DB	107.8
C2C—C1C—C6C	121.7 (3)	O2D—C7D—O3D	120.8 (3)
C7C—C1C—C6C	119.6 (3)	O2D—C7D—C1D	124.0 (3)
O1C—C2C—C1C	124.3 (3)	O3D—C7D—C1D	115.2 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1A—H1A···O2A	0.84	1.84	2.570 (3)	145
O3A—H3A···O2C	0.84	1.83	2.669 (3)	173
O1B—H1B···O2B	0.84	1.84	2.576 (3)	145
O3B—H3B···O2D	0.84	1.83	2.661 (3)	173
O1C—H1C···O2C	0.84	1.85	2.582 (3)	145
O3C—H3C···O2A	0.84	1.82	2.653 (3)	174
O1D—H1D···O2D	0.84	1.86	2.591 (3)	145
O3D—H3D···O2B	0.84	1.82	2.654 (3)	173