Threefold helical assembly via hy­droxy hydrogen bonds: the 2:1 co-crystal of bi­cyclo­[3.3.0]octane-endo-3,endo-7-diol and bi­cyclo­[3.3.0]octane-endo-3,exo-7-diol

The structure of bi­cyclo­[3.3.0]octane-endo-3,endo-7-diol and bi­cyclo­[3.3.0]octane-endo-3,exo-7-diol, C₈H₁₄O₂ form 2:1 co-crystals in the monoclinic P2₁/n space group rather than undergoing separation by means of fractional recrystallization or column chromatography.

Key indicators

Structure: I

• Single-crystal synchrotron study
• T = 100 K
• Mean [sigma](C-C) = 0.002 Å
• Disorder in main residue
• R factor = 0.049
• wR factor = 0.127
• Data-to-parameter ratio = 8.1

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT417_ALERT_2_A Short Inter D-H..H-D       H1A      ..H2C      .       1.24 Ang.
                                                    x,y,1+z  =      1_556 Check

Alert level B
PLAT411_ALERT_2_B Short Inter H...H Contact  H3A      ..H5C      .       1.95 Ang.
                                                      x,y,z  =      1_555 Check
PLAT411_ALERT_2_B Short Inter H...H Contact  H3A      ..H1CA     .       1.94 Ang.
                                                1-x,1-y,1-z  =      3_666 Check

Alert level C
PLAT088_ALERT_3_C Poor Data / Parameter Ratio ....................       8.14 Note
PLAT213_ALERT_2_C Atom C3B             has ADP max/min Ratio .....        3.1 prolat
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....        3.3 Note
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....        3.2 Note
PLAT411_ALERT_2_C Short Inter H...H Contact  H2AB     ..H7C      .       2.04 Ang.
                                                1-x,1-y,1-z  =      3_666 Check
PLAT411_ALERT_2_C Short Inter H...H Contact  H8AA     ..H6CB     .       2.06 Ang.
                                                   -1+x,y,z  =      1_455 Check
PLAT415_ALERT_2_C Short Inter D-H..H-X       H2AA     ..H2C      .       2.03 Ang.
                                                    x,y,1+z  =      1_556 Check
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600         60 Report

Alert level G
ABSMU01_ALERT_1_G  Calculation of _exptl_absorpt_correction_mu
                not performed for this radiation type.
PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite         30 Note
PLAT003_ALERT_2_G Number of Uiso or Uij Restrained non-H Atoms ...         20 Report
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          6 Report
PLAT066_ALERT_1_G Predicted and Reported Tmin&Tmax Range Identical          ? Check
PLAT171_ALERT_4_G The CIF-Embedded .res File Contains EADP Records          1 Report
PLAT175_ALERT_4_G The CIF-Embedded .res File Contains SAME Records          2 Report
PLAT178_ALERT_4_G The CIF-Embedded .res File Contains SIMU Records          1 Report
PLAT301_ALERT_3_G Main Residue  Disorder ..............(Resd  2  )       100% Note
PLAT301_ALERT_3_G Main Residue  Disorder ..............(Resd  3  )       100% Note
PLAT304_ALERT_4_G Non-Integer Number of Atoms in ..... (Resd  2  )      11.11 Check
PLAT304_ALERT_4_G Non-Integer Number of Atoms in ..... (Resd  3  )       0.89 Check
PLAT720_ALERT_4_G Number of Unusual/Non-Standard Labels ..........         27 Note
PLAT789_ALERT_4_G Atoms with Negative _atom_site_disorder_group  #         48 Check
PLAT811_ALERT_5_G No ADDSYM Analysis: Too Many Excluded Atoms ....          ! Info
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............        399 Note
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          3 Note
PLAT913_ALERT_3_G Missing # of Very Strong Reflections in FCF ....          3 Note
PLAT933_ALERT_2_G Number of OMIT Records in Embedded .res File ...          3 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.         13 Info

   1 ALERT level A = Most likely a serious problem - resolve or explain
   2 ALERT level B = A potentially serious problem, consider carefully
   8 ALERT level C = Check. Ensure it is not caused by an omission or oversight
  20 ALERT level G = General information/check it is not something unexpected

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

---

Computing details

Data collection: XDS (Kabsch, 2010); cell refinement: XDS (Kabsch, 2010); data reduction: XDS (Kabsch, 2010); program(s) used to solve structure: SHELXT2018/2 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL (Sheldrick, 2015b); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

Bicyclo[3.3.0]octane-endo-3,endo-7-diol–bicyclo[3.3.0]octane-endo-3,exo-7-diol (2/1)

Crystal data

0.66C8H14O2·0.33C8H14O2	F(000) = 468
Mr = 142.19	Dx = 1.226 Mg m^−3
Monoclinic, P21/n	Synchrotron radiation, λ = 0.71073 Å
a = 6.2758 (3) Å	Cell parameters from 1189 reflections
b = 23.6912 (10) Å	θ = 1–22°
c = 7.776 (4) Å	µ = 0.09 mm^−1
β = 91.21 (2)°	T = 100 K
V = 1155.9 (6) Å^3	Plate, colourless
Z = 6	0.02 × 0.02 × 0.01 mm

Data collection

Area detector at Australian Synchrotron diffractometer	Rint = 0.066
phi scan	θmax = 26.0°, θmin = 3.4°
16006 measured reflections	h = −7→7
2215 independent reflections	k = −29→29
2021 reflections with I > 2σ(I)	l = −9→9

Refinement

Refinement on F^2	Primary atom site location: dual
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.127	H-atom parameters constrained
S = 1.06	w = 1/[σ^2(Fo^2) + (0.0636P)^2 + 0.7974P] where P = (Fo^2 + 2Fc^2)/3
2215 reflections	(Δ/σ)max = 0.002
272 parameters	Δρmax = 0.35 e Å^−3
399 restraints	Δρmin = −0.23 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
O1A	0.06519 (17)	0.34885 (4)	1.12882 (14)	0.0164 (3)
H1A	0.172045	0.360542	1.185108	0.025*
C1A	0.0032 (2)	0.39024 (6)	1.00232 (19)	0.0153 (3)
H1AA	−0.038281	0.426466	1.058451	0.018*
C2A	0.1778 (3)	0.40019 (6)	0.8703 (2)	0.0180 (3)
H2AA	0.320485	0.399805	0.927147	0.022*
H2AB	0.157043	0.437020	0.812196	0.022*
C3A	0.1565 (2)	0.35136 (6)	0.73977 (19)	0.0156 (3)
H3A	0.178227	0.365690	0.620455	0.019*
C4A	0.3023 (2)	0.30022 (6)	0.7759 (2)	0.0159 (3)
H4AA	0.428771	0.301068	0.701986	0.019*
H4AB	0.350225	0.299338	0.897950	0.019*
C5A	0.1606 (2)	0.24957 (6)	0.73260 (18)	0.0139 (3)
H5A	0.145630	0.245438	0.604934	0.017*
O2A	0.23565 (18)	0.19773 (4)	0.80652 (14)	0.0176 (3)
H2A	0.341384	0.186208	0.752123	0.026*
C6A	−0.0529 (2)	0.26608 (6)	0.80698 (19)	0.0144 (3)
H6AA	−0.051514	0.261229	0.933452	0.017*
H6AB	−0.169963	0.243131	0.755956	0.017*
C7A	−0.0780 (2)	0.32858 (6)	0.75773 (18)	0.0141 (3)
H7A	−0.157303	0.332025	0.645327	0.017*
C8A	−0.1819 (2)	0.36634 (6)	0.89395 (19)	0.0153 (3)
H8AA	−0.264574	0.397163	0.838265	0.018*
H8AB	−0.278621	0.343960	0.966281	0.018*
O1B	0.5861 (19)	0.6170 (5)	0.6823 (12)	0.0159 (13)	0.463 (2)
H1B	0.498753	0.642917	0.659004	0.024*	0.463 (2)
C1B	0.4722 (14)	0.5665 (4)	0.7261 (9)	0.0135 (13)	0.463 (2)
H1BA	0.406620	0.569882	0.841688	0.016*	0.463 (2)
C2B	0.3060 (7)	0.55080 (17)	0.5881 (6)	0.0158 (8)	0.463 (2)
H2BA	0.223017	0.584327	0.550656	0.019*	0.463 (2)
H2BB	0.206747	0.521799	0.630977	0.019*	0.463 (2)
C3B	0.4388 (6)	0.52750 (15)	0.4400 (5)	0.0160 (8)	0.463 (2)
H3B	0.476345	0.558519	0.358849	0.019*	0.463 (2)
C4B	0.3360 (11)	0.4772 (3)	0.3397 (8)	0.0190 (15)	0.463 (2)
H4BA	0.220722	0.459703	0.406427	0.023*	0.463 (2)
H4BB	0.276787	0.489721	0.227031	0.023*	0.463 (2)
C5B	0.5197 (18)	0.4358 (4)	0.3161 (10)	0.0224 (17)	0.463 (2)
H5B	0.609958	0.448721	0.219222	0.027*	0.463 (2)
O2B	0.4395 (19)	0.3804 (5)	0.2803 (13)	0.0159 (13)	0.463 (2)
H2B	0.540541	0.357204	0.283188	0.024*	0.463 (2)
C6B	0.6454 (9)	0.4400 (3)	0.4836 (9)	0.0144 (10)	0.463 (2)
H6BA	0.792494	0.425919	0.469432	0.017*	0.463 (2)
H6BB	0.576485	0.417681	0.574584	0.017*	0.463 (2)
C7B	0.6468 (6)	0.50277 (15)	0.5295 (5)	0.0150 (7)	0.463 (2)
H7B	0.775856	0.521342	0.481846	0.018*	0.463 (2)
C8B	0.6282 (9)	0.5170 (2)	0.7203 (7)	0.0143 (11)	0.463 (2)
H8BA	0.768645	0.527798	0.770467	0.017*	0.463 (2)
H8BB	0.572815	0.484252	0.784767	0.017*	0.463 (2)
O1C	0.530 (10)	0.605 (2)	0.791 (7)	0.013 (3)	0.037 (2)
H1C	0.438106	0.630366	0.780166	0.019*	0.037 (2)
C1C	0.560 (7)	0.5784 (17)	0.631 (6)	0.016 (2)	0.037 (2)
H1CA	0.635742	0.605584	0.554858	0.019*	0.037 (2)
C2C	0.359 (8)	0.559 (3)	0.536 (11)	0.016 (3)	0.037 (2)
H2CA	0.283622	0.591060	0.480986	0.019*	0.037 (2)
H2CB	0.260712	0.539825	0.615503	0.019*	0.037 (2)
C3C	0.438 (7)	0.5170 (14)	0.399 (6)	0.016 (2)	0.037 (2)
H3C	0.450647	0.536264	0.284838	0.020*	0.037 (2)
C4C	0.302 (6)	0.4632 (16)	0.380 (7)	0.018 (3)	0.037 (2)
H4CA	0.204899	0.459624	0.478460	0.022*	0.037 (2)
H4CB	0.215178	0.464396	0.272447	0.022*	0.037 (2)
C5C	0.457 (7)	0.4142 (14)	0.377 (6)	0.018 (3)	0.037 (2)
H5C	0.394294	0.384475	0.452572	0.022*	0.037 (2)
O2C	0.478 (11)	0.389 (3)	0.215 (8)	0.016 (4)	0.037 (2)
H2C	0.357848	0.377921	0.178129	0.024*	0.037 (2)
C6C	0.657 (9)	0.4329 (17)	0.468 (10)	0.017 (3)	0.037 (2)
H6CA	0.782747	0.417484	0.408304	0.020*	0.037 (2)
H6CB	0.660553	0.418732	0.587501	0.020*	0.037 (2)
C7C	0.666 (6)	0.4971 (16)	0.467 (6)	0.016 (3)	0.037 (2)
H7C	0.778980	0.510540	0.388575	0.019*	0.037 (2)
C8C	0.694 (11)	0.525 (2)	0.646 (7)	0.014 (3)	0.037 (2)
H8CA	0.641416	0.500103	0.737544	0.017*	0.037 (2)
H8CB	0.845499	0.534256	0.670060	0.017*	0.037 (2)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1A	0.0158 (6)	0.0160 (5)	0.0173 (6)	−0.0030 (4)	−0.0062 (4)	0.0011 (4)
C1A	0.0169 (8)	0.0098 (7)	0.0189 (7)	0.0002 (5)	−0.0027 (6)	−0.0011 (5)
C2A	0.0200 (8)	0.0097 (7)	0.0242 (8)	−0.0038 (6)	−0.0005 (6)	0.0022 (6)
C3A	0.0170 (8)	0.0143 (7)	0.0156 (7)	−0.0034 (6)	0.0009 (5)	0.0026 (6)
C4A	0.0124 (7)	0.0159 (8)	0.0193 (7)	−0.0024 (5)	0.0007 (5)	−0.0022 (6)
C5A	0.0144 (7)	0.0132 (7)	0.0140 (7)	−0.0007 (5)	−0.0003 (5)	−0.0006 (5)
O2A	0.0198 (6)	0.0121 (5)	0.0211 (6)	0.0023 (4)	0.0014 (4)	−0.0002 (4)
C6A	0.0127 (7)	0.0126 (7)	0.0179 (7)	−0.0032 (5)	−0.0005 (5)	−0.0019 (6)
C7A	0.0145 (7)	0.0146 (7)	0.0130 (7)	−0.0007 (5)	−0.0039 (5)	0.0005 (5)
C8A	0.0138 (7)	0.0132 (7)	0.0186 (7)	0.0024 (5)	−0.0038 (6)	0.0005 (6)
O1B	0.014 (2)	0.0119 (10)	0.022 (4)	0.0030 (13)	−0.003 (2)	−0.0091 (19)
C1B	0.012 (2)	0.009 (2)	0.019 (3)	0.0011 (15)	−0.008 (2)	−0.004 (2)
C2B	0.0156 (19)	0.0079 (17)	0.024 (2)	−0.0010 (13)	−0.0016 (15)	0.0003 (15)
C3B	0.0218 (16)	0.0037 (16)	0.0220 (18)	−0.0016 (15)	−0.0110 (14)	0.0005 (14)
C4B	0.023 (3)	0.014 (2)	0.020 (3)	0.005 (2)	−0.009 (2)	0.000 (2)
C5B	0.029 (3)	0.012 (2)	0.026 (3)	0.0004 (19)	−0.005 (3)	−0.006 (2)
O2B	0.014 (2)	0.0119 (10)	0.022 (4)	0.0030 (13)	−0.003 (2)	−0.0091 (19)
C6B	0.0140 (19)	0.009 (2)	0.020 (2)	0.0024 (14)	−0.0048 (17)	−0.0043 (18)
C7B	0.0167 (16)	0.0077 (15)	0.0202 (19)	0.0013 (13)	−0.0088 (14)	−0.0041 (15)
C8B	0.020 (2)	0.0069 (18)	0.016 (2)	0.0010 (14)	−0.0075 (19)	−0.0003 (18)
O1C	0.011 (6)	0.010 (6)	0.017 (6)	0.003 (6)	0.000 (6)	−0.008 (6)
C1C	0.016 (4)	0.011 (4)	0.020 (4)	0.001 (4)	−0.006 (4)	−0.003 (4)
C2C	0.017 (5)	0.008 (5)	0.022 (5)	0.002 (5)	−0.004 (5)	−0.001 (5)
C3C	0.019 (4)	0.008 (4)	0.022 (4)	0.004 (4)	−0.006 (4)	0.000 (4)
C4C	0.021 (5)	0.010 (5)	0.023 (5)	0.002 (5)	−0.009 (5)	−0.001 (5)
C5C	0.020 (4)	0.012 (4)	0.023 (5)	0.003 (4)	−0.005 (4)	−0.005 (4)
O2C	0.018 (6)	0.010 (6)	0.020 (6)	0.001 (6)	−0.001 (6)	−0.007 (6)
C6C	0.020 (5)	0.008 (5)	0.022 (5)	0.004 (5)	−0.004 (5)	−0.005 (5)
C7C	0.018 (5)	0.008 (5)	0.021 (5)	0.002 (4)	−0.008 (5)	−0.003 (5)
C8C	0.015 (5)	0.008 (5)	0.020 (5)	0.002 (5)	−0.008 (5)	−0.002 (5)

Geometric parameters (Å, º)

O1A—H1A	0.8400	C4B—C5B	1.527 (11)
O1A—C1A	1.4365 (18)	C5B—H5B	1.0000
C1A—H1AA	1.0000	C5B—O2B	1.431 (12)
C1A—C2A	1.535 (2)	C5B—C6B	1.511 (9)
C1A—C8A	1.530 (2)	O2B—H2B	0.8400
C2A—H2AA	0.9900	C6B—H6BA	0.9900
C2A—H2AB	0.9900	C6B—H6BB	0.9900
C2A—C3A	1.543 (2)	C6B—C7B	1.529 (6)
C3A—H3A	1.0000	C7B—H7B	1.0000
C3A—C4A	1.540 (2)	C7B—C8B	1.528 (6)
C3A—C7A	1.577 (2)	C8B—H8BA	0.9900
C4A—H4AA	0.9900	C8B—H8BB	0.9900
C4A—H4AB	0.9900	O1C—H1C	0.8400
C4A—C5A	1.527 (2)	O1C—C1C	1.412 (18)
C5A—H5A	1.0000	C1C—H1CA	1.0000
C5A—O2A	1.4316 (18)	C1C—C2C	1.522 (18)
C5A—C6A	1.522 (2)	C1C—C8C	1.521 (18)
O2A—H2A	0.8400	C2C—H2CA	0.9900
C6A—H6AA	0.9900	C2C—H2CB	0.9900
C6A—H6AB	0.9900	C2C—C3C	1.547 (18)
C6A—C7A	1.537 (2)	C3C—H3C	1.0000
C7A—H7A	1.0000	C3C—C4C	1.540 (18)
C7A—C8A	1.542 (2)	C3C—C7C	1.585 (16)
C8A—H8AA	0.9900	C4C—H4CA	0.9900
C8A—H8AB	0.9900	C4C—H4CB	0.9900
O1B—H1B	0.8400	C4C—C5C	1.516 (17)
O1B—C1B	1.438 (12)	C5C—H5C	1.0000
C1B—H1BA	1.0000	C5C—O2C	1.410 (18)
C1B—C2B	1.527 (8)	C5C—C6C	1.496 (17)
C1B—C8B	1.530 (9)	O2C—H2C	0.8400
C2B—H2BA	0.9900	C6C—H6CA	0.9900
C2B—H2BB	0.9900	C6C—H6CB	0.9900
C2B—C3B	1.538 (6)	C6C—C7C	1.522 (17)
C3B—H3B	1.0000	C7C—H7C	1.0000
C3B—C4B	1.557 (7)	C7C—C8C	1.542 (18)
C3B—C7B	1.579 (4)	C8C—H8CA	0.9900
C4B—H4BA	0.9900	C8C—H8CB	0.9900
C4B—H4BB	0.9900
C1A—O1A—H1A	109.5	C4B—C5B—H5B	109.6
O1A—C1A—H1AA	110.9	O2B—C5B—C4B	110.4 (9)
O1A—C1A—C2A	112.09 (12)	O2B—C5B—H5B	109.6
O1A—C1A—C8A	108.43 (11)	O2B—C5B—C6B	113.8 (9)
C2A—C1A—H1AA	110.9	C6B—C5B—C4B	103.7 (5)
C8A—C1A—H1AA	110.9	C6B—C5B—H5B	109.6
C8A—C1A—C2A	103.49 (12)	C5B—O2B—H2B	109.5
C1A—C2A—H2AA	110.6	C5B—C6B—H6BA	110.7
C1A—C2A—H2AB	110.6	C5B—C6B—H6BB	110.7
C1A—C2A—C3A	105.75 (12)	C5B—C6B—C7B	105.4 (5)
H2AA—C2A—H2AB	108.7	H6BA—C6B—H6BB	108.8
C3A—C2A—H2AA	110.6	C7B—C6B—H6BA	110.7
C3A—C2A—H2AB	110.6	C7B—C6B—H6BB	110.7
C2A—C3A—H3A	110.1	C3B—C7B—H7B	110.0
C2A—C3A—C7A	105.45 (12)	C6B—C7B—C3B	104.9 (3)
C4A—C3A—C2A	115.28 (12)	C6B—C7B—H7B	110.0
C4A—C3A—H3A	110.1	C8B—C7B—C3B	105.5 (3)
C4A—C3A—C7A	105.45 (11)	C8B—C7B—C6B	116.1 (4)
C7A—C3A—H3A	110.1	C8B—C7B—H7B	110.0
C3A—C4A—H4AA	111.0	C1B—C8B—H8BA	110.7
C3A—C4A—H4AB	111.0	C1B—C8B—H8BB	110.7
H4AA—C4A—H4AB	109.0	C7B—C8B—C1B	105.0 (4)
C5A—C4A—C3A	103.72 (12)	C7B—C8B—H8BA	110.7
C5A—C4A—H4AA	111.0	C7B—C8B—H8BB	110.7
C5A—C4A—H4AB	111.0	H8BA—C8B—H8BB	108.8
C4A—C5A—H5A	109.7	C1C—O1C—H1C	109.5
O2A—C5A—C4A	113.61 (12)	O1C—C1C—H1CA	108.1
O2A—C5A—H5A	109.7	O1C—C1C—C2C	116 (3)
O2A—C5A—C6A	110.66 (12)	O1C—C1C—C8C	113 (2)
C6A—C5A—C4A	103.16 (11)	C2C—C1C—H1CA	108.1
C6A—C5A—H5A	109.7	C8C—C1C—H1CA	108.1
C5A—O2A—H2A	109.5	C8C—C1C—C2C	104 (2)
C5A—C6A—H6AA	111.0	C1C—C2C—H2CA	110.8
C5A—C6A—H6AB	111.0	C1C—C2C—H2CB	110.8
C5A—C6A—C7A	103.84 (12)	C1C—C2C—C3C	104.6 (18)
H6AA—C6A—H6AB	109.0	H2CA—C2C—H2CB	108.9
C7A—C6A—H6AA	111.0	C3C—C2C—H2CA	110.8
C7A—C6A—H6AB	111.0	C3C—C2C—H2CB	110.8
C3A—C7A—H7A	110.1	C2C—C3C—H3C	110.4
C6A—C7A—C3A	105.14 (11)	C2C—C3C—C7C	105.0 (16)
C6A—C7A—H7A	110.1	C4C—C3C—C2C	114 (3)
C6A—C7A—C8A	115.49 (12)	C4C—C3C—H3C	110.4
C8A—C7A—C3A	105.76 (11)	C4C—C3C—C7C	106.3 (15)
C8A—C7A—H7A	110.1	C7C—C3C—H3C	110.4
C1A—C8A—C7A	105.40 (12)	C3C—C4C—H4CA	110.5
C1A—C8A—H8AA	110.7	C3C—C4C—H4CB	110.5
C1A—C8A—H8AB	110.7	H4CA—C4C—H4CB	108.7
C7A—C8A—H8AA	110.7	C5C—C4C—C3C	106.2 (16)
C7A—C8A—H8AB	110.7	C5C—C4C—H4CA	110.5
H8AA—C8A—H8AB	108.8	C5C—C4C—H4CB	110.5
C1B—O1B—H1B	109.5	C4C—C5C—H5C	105.7
O1B—C1B—H1BA	111.3	O2C—C5C—C4C	114 (2)
O1B—C1B—C2B	111.9 (8)	O2C—C5C—H5C	105.7
O1B—C1B—C8B	108.1 (8)	O2C—C5C—C6C	117 (3)
C2B—C1B—H1BA	111.3	C6C—C5C—C4C	107.4 (17)
C2B—C1B—C8B	102.7 (5)	C6C—C5C—H5C	105.7
C8B—C1B—H1BA	111.3	C5C—O2C—H2C	109.5
C1B—C2B—H2BA	111.0	C5C—C6C—H6CA	109.9
C1B—C2B—H2BB	111.0	C5C—C6C—H6CB	109.9
C1B—C2B—C3B	103.9 (4)	C5C—C6C—C7C	108.9 (17)
H2BA—C2B—H2BB	109.0	H6CA—C6C—H6CB	108.3
C3B—C2B—H2BA	111.0	C7C—C6C—H6CA	109.9
C3B—C2B—H2BB	111.0	C7C—C6C—H6CB	109.9
C2B—C3B—H3B	110.3	C3C—C7C—H7C	110.1
C2B—C3B—C4B	115.1 (4)	C6C—C7C—C3C	105.5 (15)
C2B—C3B—C7B	105.0 (3)	C6C—C7C—H7C	110.1
C4B—C3B—H3B	110.3	C6C—C7C—C8C	116 (3)
C4B—C3B—C7B	105.5 (3)	C8C—C7C—C3C	105.1 (16)
C7B—C3B—H3B	110.3	C8C—C7C—H7C	110.1
C3B—C4B—H4BA	110.9	C1C—C8C—C7C	103.6 (18)
C3B—C4B—H4BB	110.9	C1C—C8C—H8CA	111.0
H4BA—C4B—H4BB	108.9	C1C—C8C—H8CB	111.0
C5B—C4B—C3B	104.2 (6)	C7C—C8C—H8CA	111.0
C5B—C4B—H4BA	110.9	C7C—C8C—H8CB	111.0
C5B—C4B—H4BB	110.9	H8CA—C8C—H8CB	109.0
O1A—C1A—C2A—C3A	80.65 (15)	C3B—C7B—C8B—C1B	−21.7 (5)
O1A—C1A—C8A—C7A	−82.34 (14)	C4B—C3B—C7B—C6B	−2.7 (5)
C1A—C2A—C3A—C4A	−94.67 (15)	C4B—C3B—C7B—C8B	−125.9 (4)
C1A—C2A—C3A—C7A	21.20 (15)	C4B—C5B—C6B—C7B	−40.4 (9)
C2A—C1A—C8A—C7A	36.83 (14)	C5B—C6B—C7B—C3B	26.3 (7)
C2A—C3A—C4A—C5A	140.20 (13)	C5B—C6B—C7B—C8B	142.3 (6)
C2A—C3A—C7A—C6A	−121.19 (12)	O2B—C5B—C6B—C7B	−160.3 (8)
C2A—C3A—C7A—C8A	1.47 (15)	C6B—C7B—C8B—C1B	−137.4 (5)
C3A—C4A—C5A—O2A	−161.11 (12)	C7B—C3B—C4B—C5B	−21.4 (7)
C3A—C4A—C5A—C6A	−41.26 (14)	C8B—C1B—C2B—C3B	−41.7 (6)
C3A—C7A—C8A—C1A	−23.66 (14)	O1C—C1C—C2C—C3C	−163 (4)
C4A—C3A—C7A—C6A	1.22 (14)	O1C—C1C—C8C—C7C	168 (4)
C4A—C3A—C7A—C8A	123.88 (12)	C1C—C2C—C3C—C4C	137 (5)
C4A—C5A—C6A—C7A	42.17 (14)	C1C—C2C—C3C—C7C	21 (5)
C5A—C6A—C7A—C3A	−26.43 (14)	C2C—C1C—C8C—C7C	42 (5)
C5A—C6A—C7A—C8A	−142.58 (12)	C2C—C3C—C4C—C5C	−134 (4)
O2A—C5A—C6A—C7A	164.03 (11)	C2C—C3C—C7C—C6C	127 (5)
C6A—C7A—C8A—C1A	92.14 (14)	C2C—C3C—C7C—C8C	4 (5)
C7A—C3A—C4A—C5A	24.33 (14)	C3C—C4C—C5C—O2C	−107 (4)
C8A—C1A—C2A—C3A	−35.97 (14)	C3C—C4C—C5C—C6C	24 (5)
O1B—C1B—C2B—C3B	74.0 (7)	C3C—C7C—C8C—C1C	−28 (5)
O1B—C1B—C8B—C7B	−79.0 (7)	C4C—C3C—C7C—C6C	6 (5)
C1B—C2B—C3B—C4B	143.5 (5)	C4C—C3C—C7C—C8C	−117 (5)
C1B—C2B—C3B—C7B	28.0 (5)	C4C—C5C—C6C—C7C	−21 (6)
C2B—C1B—C8B—C7B	39.4 (6)	C5C—C6C—C7C—C3C	9 (6)
C2B—C3B—C4B—C5B	−136.7 (5)	C5C—C6C—C7C—C8C	125 (5)
C2B—C3B—C7B—C6B	119.3 (4)	O2C—C5C—C6C—C7C	109 (5)
C2B—C3B—C7B—C8B	−3.9 (4)	C6C—C7C—C8C—C1C	−144 (4)
C3B—C4B—C5B—O2B	160.1 (7)	C7C—C3C—C4C—C5C	−18 (4)
C3B—C4B—C5B—C6B	38.0 (9)	C8C—C1C—C2C—C3C	−40 (5)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1A—H1A···O1B^i	0.84	1.89	2.732 (12)	177
O1A—H1A···O2B^ii	0.84	1.88	2.710 (12)	170
O1A—H1A···O1C^i	0.84	2.05	2.83 (6)	154
O1A—H1A···O2C^ii	0.84	2.04	2.82 (7)	155
C2A—H2AA···O1C^i	0.99	2.37	3.18 (5)	139
C2A—H2AA···O2C^ii	0.99	2.44	3.25 (6)	139
O2A—H2A···O1A^iii	0.84	1.91	2.7432 (16)	173
O1B—H1B···O2A^iv	0.84	1.98	2.784 (12)	159
O2B—H2B···O2A^iii	0.84	1.79	2.629 (12)	173
O1C—H1C···O2A^iv	0.84	2.04	2.86 (5)	164

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