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[1,1′-Bicyclohexane]-1,1′-diol

Z. Mtendeni, E. C. Hosten and R. Betz

The title compound, C₁₂H₂₂O₂, is a symmetric diol derived from the pinacol coupling of cyclohexanone. The asymmetric unit contains three complete molecules. The cyclohexane moieties adopt chair conformations. Cooperative hydrogen bonding connects the individual molecules to infinite chains propagating along the crystallographic a-axis direction.

Keywords: crystal structure.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S2414314623009690/bt4141sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S2414314623009690/bt4141Isup2.hkl Contains datablock I
	Chemical Markup Language (CML) file https://doi.org/10.1107/S2414314623009690/bt4141Isup3.cml Supplementary material

CCDC reference: 2306283

checkCIF report

Key indicators

Structure: I

Single-crystal X-ray study
T = 200 K
Mean (C-C) = 0.002 Å
R factor = 0.042
wR factor = 0.110
Data-to-parameter ratio = 22.4

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600          6 Report

Alert level G
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............         12 Report

Author Response: H atoms on hydroxyl groups disordered over two positions

PLAT300_ALERT_4_G Atom Site Occupancy of H1A        Constrained at        0.5 Check

Author Response: H atoms on hydroxyl groups disordered over two positions

PLAT300_ALERT_4_G Atom Site Occupancy of H1B        Constrained at        0.5 Check

Author Response: H atoms on hydroxyl groups disordered over two positions

PLAT300_ALERT_4_G Atom Site Occupancy of H2A        Constrained at        0.5 Check

Author Response: H atoms on hydroxyl groups disordered over two positions

PLAT300_ALERT_4_G Atom Site Occupancy of H2B        Constrained at        0.5 Check

Author Response: H atoms on hydroxyl groups disordered over two positions

PLAT300_ALERT_4_G Atom Site Occupancy of H3A        Constrained at        0.5 Check

Author Response: H atoms on hydroxyl groups disordered over two positions

PLAT300_ALERT_4_G Atom Site Occupancy of H3B        Constrained at        0.5 Check

Author Response: H atoms on hydroxyl groups disordered over two positions

PLAT300_ALERT_4_G Atom Site Occupancy of H4A        Constrained at        0.5 Check

Author Response: H atoms on hydroxyl groups disordered over two positions

PLAT300_ALERT_4_G Atom Site Occupancy of H4B        Constrained at        0.5 Check

Author Response: H atoms on hydroxyl groups disordered over two positions

PLAT300_ALERT_4_G Atom Site Occupancy of H5A        Constrained at        0.5 Check

Author Response: H atoms on hydroxyl groups disordered over two positions

PLAT300_ALERT_4_G Atom Site Occupancy of H5B        Constrained at        0.5 Check

Author Response: H atoms on hydroxyl groups disordered over two positions

PLAT300_ALERT_4_G Atom Site Occupancy of H6A        Constrained at        0.5 Check

Author Response: H atoms on hydroxyl groups disordered over two positions

PLAT300_ALERT_4_G Atom Site Occupancy of H6B        Constrained at        0.5 Check

Author Response: H atoms on hydroxyl groups disordered over two positions

PLAT414_ALERT_2_G Short Intra D-H..H-X       H2B      ..H16B     .       2.04 Ang.
                                                      x,y,z  =      1_555 Check

Author Response: situation checked

PLAT414_ALERT_2_G Short Intra D-H..H-X       H3A      ..H42B     .       2.12 Ang.
                                                      x,y,z  =      1_555 Check

Author Response: situation checked

PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          1 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         57 Note
PLAT933_ALERT_2_G Number of HKL-OMIT Records in Embedded .res File          1 Note

Author Response: one obnoxious reflection omitted from final refinement cycles

PLAT941_ALERT_3_G Average HKL Measurement Multiplicity ...........        3.6 Low

Author Response: situation checked

PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.         22 Info
PLAT992_ALERT_5_G Repd & Actual _reflns_number_gt Values Differ by          3 Check

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

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

Computing details top

[1,1'-Bicyclohexane]-1,1'-diol top

Crystal data top

C₁₂H₂₂O₂	Z = 6
M_r = 198.29	F(000) = 660
Triclinic, P1	D_x = 1.160 Mg m⁻³
a = 9.8996 (7) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.0299 (7) Å	Cell parameters from 9559 reflections
c = 17.9841 (13) Å	θ = 2.4–28.3°
α = 73.810 (3)°	µ = 0.08 mm⁻¹
β = 86.774 (4)°	T = 200 K
γ = 83.592 (3)°	Blocks, colourless
V = 1703.6 (2) Å³	0.60 × 0.49 × 0.18 mm

Data collection top

Bruker APEXII CCD diffractometer	8498 independent reflections
Radiation source: sealed tube	6202 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.024
φ and ω scans	θ_max = 28.4°, θ_min = 2.1°
Absorption correction: numerical (SADABS; Krause et al., 2015)	h = −13→13
T_min = 0.941, T_max = 1.000	k = −13→13
30730 measured reflections	l = −23→24

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.110	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0505P)² + 0.3176P] where P = (F_o² + 2F_c²)/3
8498 reflections	(Δ/σ)_max = 0.001
380 parameters	Δρ_max = 0.29 e Å⁻³
0 restraints	Δρ_min = −0.19 e Å⁻³

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
O1	0.56808 (8)	0.29971 (10)	0.76040 (6)	0.0365 (2)
H1A	0.515794	0.361612	0.741310	0.055*	0.5
H1B	0.523094	0.239516	0.778010	0.055*	0.5
O2	0.93801 (8)	0.22716 (9)	0.73920 (6)	0.0348 (2)
H2A	0.988346	0.221703	0.703067	0.052*	0.5
H2B	0.963946	0.239903	0.772366	0.052*	0.5
O3	0.14540 (8)	0.28120 (8)	0.82788 (4)	0.02719 (19)
H3A	0.078291	0.237734	0.817663	0.041*	0.5
H3B	0.198291	0.321434	0.789254	0.027*	0.5
O4	0.36472 (8)	0.11455 (8)	0.79255 (5)	0.02812 (19)
H4A	0.435244	0.154297	0.788666	0.042*	0.5
H4B	0.332044	0.165297	0.754866	0.042*	0.5
O5	0.31219 (8)	0.43533 (8)	0.70791 (5)	0.02771 (19)
H5A	0.268910	0.380544	0.744571	0.042*	0.5
H5B	0.393910	0.423744	0.706071	0.042*	0.5
O6	0.19507 (8)	0.23358 (8)	0.66154 (5)	0.02741 (19)
H6A	0.243395	0.208154	0.700916	0.041*	0.5
H6B	0.101960	0.234254	0.678021	0.041*	0.5
C11	0.70830 (10)	0.32190 (11)	0.76342 (6)	0.0201 (2)
C12	0.72690 (12)	0.46897 (12)	0.71186 (7)	0.0286 (3)
H12A	0.825354	0.479829	0.704790	0.034*
H12B	0.690309	0.479139	0.660247	0.034*
C13	0.65728 (14)	0.58557 (14)	0.74410 (9)	0.0384 (3)
H13A	0.679433	0.676950	0.710034	0.046*
H13B	0.557472	0.583494	0.744701	0.046*
C14	0.70274 (14)	0.56951 (15)	0.82538 (9)	0.0405 (3)
H14A	0.655153	0.644961	0.845533	0.049*
H14B	0.801703	0.577072	0.824556	0.049*
C15	0.67119 (14)	0.42892 (15)	0.87778 (8)	0.0374 (3)
H15A	0.571577	0.424348	0.881147	0.045*
H15B	0.702873	0.418494	0.930530	0.045*
C16	0.73978 (13)	0.30961 (13)	0.84762 (7)	0.0304 (3)
H16A	0.710496	0.220570	0.880910	0.037*
H16B	0.839411	0.306066	0.852129	0.037*
C21	0.79768 (10)	0.20756 (11)	0.73319 (6)	0.0195 (2)
C22	0.77309 (13)	0.06019 (12)	0.78313 (7)	0.0305 (3)
H22A	0.806832	0.047227	0.835712	0.037*
H22B	0.673976	0.052434	0.788016	0.037*
C23	0.84177 (14)	−0.05635 (13)	0.75082 (8)	0.0367 (3)
H23A	0.941711	−0.057487	0.752324	0.044*
H23B	0.815950	−0.147337	0.783547	0.044*
C24	0.80068 (15)	−0.03633 (14)	0.66817 (9)	0.0403 (3)
H24A	0.846954	−0.112472	0.648114	0.048*
H24B	0.701294	−0.039465	0.666676	0.048*
C25	0.83963 (14)	0.10308 (15)	0.61805 (8)	0.0374 (3)
H25A	0.811717	0.116417	0.564250	0.045*
H25B	0.939634	0.103575	0.617425	0.045*
C26	0.77213 (12)	0.22312 (13)	0.64813 (7)	0.0273 (3)
H26A	0.805802	0.311191	0.616424	0.033*
H26B	0.672844	0.230645	0.641055	0.033*
C31	0.21725 (11)	0.18418 (11)	0.89152 (6)	0.0200 (2)
C32	0.11161 (12)	0.14108 (13)	0.95726 (7)	0.0301 (3)
H32A	0.038665	0.099471	0.938646	0.036*
H32B	0.155602	0.068901	1.000863	0.036*
C33	0.04866 (13)	0.26421 (15)	0.98627 (8)	0.0373 (3)
H33A	−0.004750	0.331300	0.944500	0.045*
H33B	−0.014316	0.230173	1.030580	0.045*
C34	0.15628 (14)	0.33828 (16)	1.01140 (8)	0.0386 (3)
H34A	0.204689	0.274007	1.056236	0.046*
H34B	0.112317	0.419662	1.027632	0.046*
C35	0.25723 (13)	0.38674 (13)	0.94504 (8)	0.0325 (3)
H35A	0.329264	0.430854	0.962745	0.039*
H35B	0.210061	0.457459	0.902040	0.039*
C36	0.32149 (11)	0.26445 (12)	0.91615 (7)	0.0256 (2)
H36A	0.376900	0.199415	0.957738	0.031*
H36B	0.383335	0.299910	0.871499	0.031*
C41	0.28844 (11)	0.05912 (11)	0.86257 (6)	0.0204 (2)
C42	0.18433 (12)	−0.02606 (12)	0.84183 (7)	0.0278 (3)
H42A	0.126505	−0.062742	0.888178	0.033*
H42B	0.124784	0.036153	0.801333	0.033*
C43	0.25017 (14)	−0.14774 (13)	0.81273 (8)	0.0358 (3)
H43A	0.178583	−0.200925	0.802082	0.043*
H43B	0.301525	−0.111365	0.763725	0.043*
C44	0.34571 (15)	−0.24392 (13)	0.87229 (9)	0.0387 (3)
H44A	0.390810	−0.319501	0.851373	0.046*
H44B	0.293121	−0.287081	0.919707	0.046*
C45	0.45267 (14)	−0.16253 (13)	0.89230 (8)	0.0359 (3)
H45A	0.511192	−0.128125	0.845925	0.043*
H45B	0.510917	−0.225632	0.933167	0.043*
C46	0.38887 (13)	−0.03865 (13)	0.92049 (7)	0.0301 (3)
H46A	0.461886	0.014868	0.929086	0.036*
H46B	0.340597	−0.073931	0.970704	0.036*
C51	0.24752 (10)	0.47484 (11)	0.63405 (6)	0.0207 (2)
C52	0.09989 (11)	0.52910 (12)	0.64770 (7)	0.0245 (2)
H52A	0.051896	0.555035	0.598091	0.029*
H52B	0.054060	0.453345	0.684257	0.029*
C53	0.08875 (13)	0.65513 (13)	0.68017 (7)	0.0301 (3)
H53A	−0.008295	0.686594	0.687308	0.036*
H53B	0.131466	0.628397	0.731396	0.036*
C54	0.15860 (13)	0.77386 (13)	0.62562 (8)	0.0343 (3)
H54A	0.154109	0.853302	0.648551	0.041*
H54B	0.111170	0.806044	0.575789	0.041*
C55	0.30656 (13)	0.72491 (13)	0.61147 (8)	0.0353 (3)
H55A	0.355879	0.704091	0.660420	0.042*
H55B	0.348864	0.801160	0.573165	0.042*
C56	0.32183 (12)	0.59495 (13)	0.58173 (7)	0.0294 (3)
H56A	0.419645	0.562844	0.578249	0.035*
H56B	0.285412	0.619887	0.528935	0.035*
C61	0.25485 (10)	0.34261 (12)	0.60330 (6)	0.0209 (2)
C62	0.17544 (12)	0.36547 (13)	0.52915 (7)	0.0280 (3)
H62A	0.078056	0.390171	0.539822	0.034*
H62B	0.208641	0.444956	0.488752	0.034*
C63	0.18968 (13)	0.23674 (15)	0.49851 (8)	0.0352 (3)
H63A	0.144320	0.161208	0.535547	0.042*
H63B	0.143072	0.259795	0.448569	0.042*
C64	0.33798 (14)	0.18484 (16)	0.48677 (8)	0.0391 (3)
H64A	0.342635	0.098089	0.470299	0.047*
H64B	0.381297	0.255816	0.445447	0.047*
C65	0.41386 (13)	0.15677 (15)	0.56150 (8)	0.0353 (3)
H65A	0.510863	0.127499	0.552576	0.042*
H65B	0.375663	0.079819	0.601439	0.042*
C66	0.40235 (11)	0.28693 (14)	0.59025 (7)	0.0283 (3)
H66A	0.447745	0.360803	0.551963	0.034*
H66B	0.450876	0.265098	0.639524	0.034*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0136 (4)	0.0469 (6)	0.0588 (6)	−0.0060 (4)	0.0016 (4)	−0.0298 (5)
O2	0.0141 (4)	0.0387 (5)	0.0583 (6)	−0.0014 (3)	−0.0053 (4)	−0.0238 (4)
O3	0.0292 (4)	0.0283 (4)	0.0214 (4)	0.0039 (3)	−0.0054 (3)	−0.0041 (3)
O4	0.0303 (4)	0.0261 (4)	0.0248 (4)	−0.0019 (3)	0.0046 (3)	−0.0031 (3)
O5	0.0307 (4)	0.0289 (4)	0.0224 (4)	−0.0032 (3)	−0.0099 (3)	−0.0032 (3)
O6	0.0322 (4)	0.0269 (4)	0.0224 (4)	−0.0062 (3)	0.0028 (3)	−0.0049 (3)
C11	0.0134 (5)	0.0236 (5)	0.0237 (5)	−0.0030 (4)	−0.0018 (4)	−0.0068 (4)
C12	0.0285 (6)	0.0220 (6)	0.0339 (6)	−0.0021 (5)	0.0011 (5)	−0.0060 (5)
C13	0.0366 (7)	0.0257 (7)	0.0540 (9)	0.0016 (5)	−0.0029 (6)	−0.0142 (6)
C14	0.0332 (7)	0.0404 (8)	0.0595 (9)	−0.0046 (6)	−0.0007 (6)	−0.0323 (7)
C15	0.0332 (7)	0.0497 (8)	0.0378 (7)	−0.0039 (6)	0.0011 (6)	−0.0266 (6)
C16	0.0319 (6)	0.0357 (7)	0.0258 (6)	−0.0004 (5)	−0.0023 (5)	−0.0127 (5)
C21	0.0133 (5)	0.0227 (5)	0.0230 (5)	−0.0023 (4)	−0.0023 (4)	−0.0066 (4)
C22	0.0346 (6)	0.0224 (6)	0.0320 (6)	−0.0028 (5)	0.0004 (5)	−0.0037 (5)
C23	0.0400 (7)	0.0225 (6)	0.0479 (8)	0.0022 (5)	−0.0084 (6)	−0.0107 (6)
C24	0.0390 (7)	0.0350 (7)	0.0544 (9)	0.0052 (6)	−0.0131 (6)	−0.0258 (7)
C25	0.0381 (7)	0.0459 (8)	0.0327 (7)	0.0054 (6)	−0.0043 (6)	−0.0211 (6)
C26	0.0273 (6)	0.0307 (6)	0.0245 (6)	0.0022 (5)	−0.0043 (5)	−0.0096 (5)
C31	0.0200 (5)	0.0220 (5)	0.0174 (5)	−0.0045 (4)	−0.0033 (4)	−0.0030 (4)
C32	0.0308 (6)	0.0334 (7)	0.0259 (6)	−0.0116 (5)	0.0050 (5)	−0.0055 (5)
C33	0.0333 (7)	0.0467 (8)	0.0339 (7)	−0.0088 (6)	0.0116 (5)	−0.0149 (6)
C34	0.0420 (7)	0.0470 (8)	0.0325 (7)	−0.0024 (6)	0.0015 (6)	−0.0215 (6)
C35	0.0337 (6)	0.0318 (7)	0.0379 (7)	−0.0071 (5)	−0.0035 (5)	−0.0172 (5)
C36	0.0231 (5)	0.0305 (6)	0.0263 (6)	−0.0070 (5)	−0.0026 (4)	−0.0110 (5)
C41	0.0212 (5)	0.0202 (5)	0.0191 (5)	−0.0043 (4)	−0.0039 (4)	−0.0025 (4)
C42	0.0269 (6)	0.0230 (6)	0.0344 (6)	−0.0051 (5)	−0.0087 (5)	−0.0069 (5)
C43	0.0387 (7)	0.0278 (6)	0.0465 (8)	−0.0048 (5)	−0.0130 (6)	−0.0164 (6)
C44	0.0456 (8)	0.0222 (6)	0.0478 (8)	0.0008 (6)	−0.0074 (6)	−0.0091 (6)
C45	0.0379 (7)	0.0282 (7)	0.0399 (7)	0.0069 (5)	−0.0160 (6)	−0.0077 (6)
C46	0.0344 (6)	0.0276 (6)	0.0279 (6)	0.0010 (5)	−0.0127 (5)	−0.0061 (5)
C51	0.0169 (5)	0.0250 (6)	0.0178 (5)	−0.0011 (4)	−0.0032 (4)	−0.0016 (4)
C52	0.0184 (5)	0.0263 (6)	0.0276 (6)	0.0000 (4)	−0.0014 (4)	−0.0060 (5)
C53	0.0290 (6)	0.0286 (6)	0.0325 (6)	0.0009 (5)	−0.0008 (5)	−0.0094 (5)
C54	0.0400 (7)	0.0252 (6)	0.0362 (7)	−0.0019 (5)	−0.0056 (6)	−0.0060 (5)
C55	0.0360 (7)	0.0294 (7)	0.0380 (7)	−0.0108 (5)	−0.0008 (6)	−0.0025 (5)
C56	0.0265 (6)	0.0310 (6)	0.0265 (6)	−0.0056 (5)	0.0023 (5)	−0.0003 (5)
C61	0.0156 (5)	0.0271 (6)	0.0182 (5)	−0.0001 (4)	−0.0011 (4)	−0.0038 (4)
C62	0.0237 (5)	0.0370 (7)	0.0232 (6)	0.0034 (5)	−0.0064 (4)	−0.0094 (5)
C63	0.0309 (6)	0.0469 (8)	0.0321 (7)	0.0050 (6)	−0.0098 (5)	−0.0196 (6)
C64	0.0362 (7)	0.0531 (9)	0.0330 (7)	0.0083 (6)	−0.0047 (6)	−0.0246 (6)
C65	0.0266 (6)	0.0467 (8)	0.0343 (7)	0.0107 (6)	−0.0036 (5)	−0.0189 (6)
C66	0.0171 (5)	0.0435 (7)	0.0247 (6)	0.0029 (5)	−0.0018 (4)	−0.0119 (5)

Geometric parameters (Å, º) top

O1—C11	1.4366 (12)	C33—H33B	0.9900
O1—H1A	0.7750	C34—C35	1.5199 (18)
O1—H1B	0.7750	C34—H34A	0.9900
O2—C21	1.4387 (12)	C34—H34B	0.9900
O2—H2A	0.8069	C35—C36	1.5242 (17)
O2—H2B	0.7106	C35—H35A	0.9900
O3—C31	1.4418 (13)	C35—H35B	0.9900
O3—H3A	0.8879	C36—H36A	0.9900
O3—H3B	0.8772	C36—H36B	0.9900
O4—C41	1.4357 (12)	C41—C42	1.5325 (15)
O4—H4A	0.8321	C41—C46	1.5377 (16)
O4—H4B	0.7865	C42—C43	1.5259 (18)
O5—C51	1.4412 (13)	C42—H42A	0.9900
O5—H5A	0.8596	C42—H42B	0.9900
O5—H5B	0.8045	C43—C44	1.5187 (19)
O6—C61	1.4419 (12)	C43—H43A	0.9900
O6—H6A	0.8399	C43—H43B	0.9900
O6—H6B	0.9521	C44—C45	1.5220 (19)
C11—C16	1.5317 (16)	C44—H44A	0.9900
C11—C12	1.5324 (15)	C44—H44B	0.9900
C11—C21	1.5685 (15)	C45—C46	1.5296 (18)
C12—C13	1.5270 (18)	C45—H45A	0.9900
C12—H12A	0.9900	C45—H45B	0.9900
C12—H12B	0.9900	C46—H46A	0.9900
C13—C14	1.514 (2)	C46—H46B	0.9900
C13—H13A	0.9900	C51—C52	1.5326 (15)
C13—H13B	0.9900	C51—C56	1.5380 (15)
C14—C15	1.516 (2)	C51—C61	1.5662 (16)
C14—H14A	0.9900	C52—C53	1.5246 (17)
C14—H14B	0.9900	C52—H52A	0.9900
C15—C16	1.5252 (18)	C52—H52B	0.9900
C15—H15A	0.9900	C53—C54	1.5214 (17)
C15—H15B	0.9900	C53—H53A	0.9900
C16—H16A	0.9900	C53—H53B	0.9900
C16—H16B	0.9900	C54—C55	1.5226 (18)
C21—C26	1.5265 (16)	C54—H54A	0.9900
C21—C22	1.5382 (15)	C54—H54B	0.9900
C22—C23	1.5241 (18)	C55—C56	1.5309 (18)
C22—H22A	0.9900	C55—H55A	0.9900
C22—H22B	0.9900	C55—H55B	0.9900
C23—C24	1.516 (2)	C56—H56A	0.9900
C23—H23A	0.9900	C56—H56B	0.9900
C23—H23B	0.9900	C61—C66	1.5335 (15)
C24—C25	1.515 (2)	C61—C62	1.5350 (16)
C24—H24A	0.9900	C62—C63	1.5290 (18)
C24—H24B	0.9900	C62—H62A	0.9900
C25—C26	1.5270 (18)	C62—H62B	0.9900
C25—H25A	0.9900	C63—C64	1.5254 (18)
C25—H25B	0.9900	C63—H63A	0.9900
C26—H26A	0.9900	C63—H63B	0.9900
C26—H26B	0.9900	C64—C65	1.5183 (18)
C31—C36	1.5314 (15)	C64—H64A	0.9900
C31—C32	1.5346 (14)	C64—H64B	0.9900
C31—C41	1.5705 (16)	C65—C66	1.5236 (18)
C32—C33	1.5287 (18)	C65—H65A	0.9900
C32—H32A	0.9900	C65—H65B	0.9900
C32—H32B	0.9900	C66—H66A	0.9900
C33—C34	1.5196 (19)	C66—H66B	0.9900
C33—H33A	0.9900

C11—O1—H1A	120.0	C34—C35—H35B	109.5
C11—O1—H1B	136.4	C36—C35—H35B	109.5
H1A—O1—H1B	103.2	H35A—C35—H35B	108.1
C21—O2—H2A	117.1	C35—C36—C31	113.42 (10)
C21—O2—H2B	123.0	C35—C36—H36A	108.9
H2A—O2—H2B	119.9	C31—C36—H36A	108.9
C31—O3—H3A	106.4	C35—C36—H36B	108.9
C31—O3—H3B	114.1	C31—C36—H36B	108.9
H3A—O3—H3B	118.1	H36A—C36—H36B	107.7
C41—O4—H4A	126.5	O4—C41—C42	106.37 (9)
C41—O4—H4B	123.6	O4—C41—C46	107.05 (9)
H4A—O4—H4B	95.3	C42—C41—C46	109.45 (9)
C51—O5—H5A	114.5	O4—C41—C31	108.51 (8)
C51—O5—H5B	115.3	C42—C41—C31	111.61 (9)
H5A—O5—H5B	118.9	C46—C41—C31	113.48 (9)
C61—O6—H6A	109.8	C43—C42—C41	112.97 (10)
C61—O6—H6B	126.1	C43—C42—H42A	109.0
H6A—O6—H6B	108.6	C41—C42—H42A	109.0
O1—C11—C16	108.21 (9)	C43—C42—H42B	109.0
O1—C11—C12	107.43 (9)	C41—C42—H42B	109.0
C16—C11—C12	110.59 (10)	H42A—C42—H42B	107.8
O1—C11—C21	108.01 (9)	C44—C43—C42	110.78 (11)
C16—C11—C21	110.92 (9)	C44—C43—H43A	109.5
C12—C11—C21	111.52 (8)	C42—C43—H43A	109.5
C13—C12—C11	113.94 (10)	C44—C43—H43B	109.5
C13—C12—H12A	108.8	C42—C43—H43B	109.5
C11—C12—H12A	108.8	H43A—C43—H43B	108.1
C13—C12—H12B	108.8	C43—C44—C45	110.29 (11)
C11—C12—H12B	108.8	C43—C44—H44A	109.6
H12A—C12—H12B	107.7	C45—C44—H44A	109.6
C14—C13—C12	111.01 (11)	C43—C44—H44B	109.6
C14—C13—H13A	109.4	C45—C44—H44B	109.6
C12—C13—H13A	109.4	H44A—C44—H44B	108.1
C14—C13—H13B	109.4	C44—C45—C46	112.07 (11)
C12—C13—H13B	109.4	C44—C45—H45A	109.2
H13A—C13—H13B	108.0	C46—C45—H45A	109.2
C13—C14—C15	109.87 (11)	C44—C45—H45B	109.2
C13—C14—H14A	109.7	C46—C45—H45B	109.2
C15—C14—H14A	109.7	H45A—C45—H45B	107.9
C13—C14—H14B	109.7	C45—C46—C41	112.44 (10)
C15—C14—H14B	109.7	C45—C46—H46A	109.1
H14A—C14—H14B	108.2	C41—C46—H46A	109.1
C14—C15—C16	111.40 (11)	C45—C46—H46B	109.1
C14—C15—H15A	109.3	C41—C46—H46B	109.1
C16—C15—H15A	109.3	H46A—C46—H46B	107.8
C14—C15—H15B	109.3	O5—C51—C52	107.05 (9)
C16—C15—H15B	109.3	O5—C51—C56	106.55 (9)
H15A—C15—H15B	108.0	C52—C51—C56	109.20 (9)
C15—C16—C11	114.03 (11)	O5—C51—C61	108.20 (8)
C15—C16—H16A	108.7	C52—C51—C61	111.28 (9)
C11—C16—H16A	108.7	C56—C51—C61	114.21 (9)
C15—C16—H16B	108.7	C53—C52—C51	112.79 (10)
C11—C16—H16B	108.7	C53—C52—H52A	109.0
H16A—C16—H16B	107.6	C51—C52—H52A	109.0
O2—C21—C26	107.70 (9)	C53—C52—H52B	109.0
O2—C21—C22	108.24 (9)	C51—C52—H52B	109.0
C26—C21—C22	110.64 (10)	H52A—C52—H52B	107.8
O2—C21—C11	107.67 (8)	C54—C53—C52	110.60 (10)
C26—C21—C11	111.40 (9)	C54—C53—H53A	109.5
C22—C21—C11	111.03 (9)	C52—C53—H53A	109.5
C23—C22—C21	113.89 (10)	C54—C53—H53B	109.5
C23—C22—H22A	108.8	C52—C53—H53B	109.5
C21—C22—H22A	108.8	H53A—C53—H53B	108.1
C23—C22—H22B	108.8	C53—C54—C55	110.03 (10)
C21—C22—H22B	108.8	C53—C54—H54A	109.7
H22A—C22—H22B	107.7	C55—C54—H54A	109.7
C24—C23—C22	111.02 (11)	C53—C54—H54B	109.7
C24—C23—H23A	109.4	C55—C54—H54B	109.7
C22—C23—H23A	109.4	H54A—C54—H54B	108.2
C24—C23—H23B	109.4	C54—C55—C56	112.60 (11)
C22—C23—H23B	109.4	C54—C55—H55A	109.1
H23A—C23—H23B	108.0	C56—C55—H55A	109.1
C25—C24—C23	109.52 (11)	C54—C55—H55B	109.1
C25—C24—H24A	109.8	C56—C55—H55B	109.1
C23—C24—H24A	109.8	H55A—C55—H55B	107.8
C25—C24—H24B	109.8	C55—C56—C51	112.75 (10)
C23—C24—H24B	109.8	C55—C56—H56A	109.0
H24A—C24—H24B	108.2	C51—C56—H56A	109.0
C24—C25—C26	111.29 (11)	C55—C56—H56B	109.0
C24—C25—H25A	109.4	C51—C56—H56B	109.0
C26—C25—H25A	109.4	H56A—C56—H56B	107.8
C24—C25—H25B	109.4	O6—C61—C66	106.78 (9)
C26—C25—H25B	109.4	O6—C61—C62	106.53 (9)
H25A—C25—H25B	108.0	C66—C61—C62	109.43 (9)
C21—C26—C25	114.23 (10)	O6—C61—C51	108.35 (8)
C21—C26—H26A	108.7	C66—C61—C51	111.55 (9)
C25—C26—H26A	108.7	C62—C61—C51	113.83 (9)
C21—C26—H26B	108.7	C63—C62—C61	112.64 (10)
C25—C26—H26B	108.7	C63—C62—H62A	109.1
H26A—C26—H26B	107.6	C61—C62—H62A	109.1
O3—C31—C36	106.58 (9)	C63—C62—H62B	109.1
O3—C31—C32	106.55 (9)	C61—C62—H62B	109.1
C36—C31—C32	109.71 (9)	H62A—C62—H62B	107.8
O3—C31—C41	108.42 (8)	C64—C63—C62	112.29 (11)
C36—C31—C41	111.44 (9)	C64—C63—H63A	109.1
C32—C31—C41	113.76 (9)	C62—C63—H63A	109.1
C33—C32—C31	112.37 (10)	C64—C63—H63B	109.1
C33—C32—H32A	109.1	C62—C63—H63B	109.1
C31—C32—H32A	109.1	H63A—C63—H63B	107.9
C33—C32—H32B	109.1	C65—C64—C63	110.19 (10)
C31—C32—H32B	109.1	C65—C64—H64A	109.6
H32A—C32—H32B	107.9	C63—C64—H64A	109.6
C34—C33—C32	111.83 (11)	C65—C64—H64B	109.6
C34—C33—H33A	109.3	C63—C64—H64B	109.6
C32—C33—H33A	109.3	H64A—C64—H64B	108.1
C34—C33—H33B	109.3	C64—C65—C66	110.68 (11)
C32—C33—H33B	109.3	C64—C65—H65A	109.5
H33A—C33—H33B	107.9	C66—C65—H65A	109.5
C33—C34—C35	110.14 (11)	C64—C65—H65B	109.5
C33—C34—H34A	109.6	C66—C65—H65B	109.5
C35—C34—H34A	109.6	H65A—C65—H65B	108.1
C33—C34—H34B	109.6	C65—C66—C61	113.16 (10)
C35—C34—H34B	109.6	C65—C66—H66A	108.9
H34A—C34—H34B	108.1	C61—C66—H66A	108.9
C34—C35—C36	110.82 (10)	C65—C66—H66B	108.9
C34—C35—H35A	109.5	C61—C66—H66B	108.9
C36—C35—H35A	109.5	H66A—C66—H66B	107.8

O1—C11—C12—C13	69.48 (13)	C32—C31—C41—C42	52.39 (12)
C16—C11—C12—C13	−48.41 (13)	O3—C31—C41—C46	169.81 (9)
C21—C11—C12—C13	−172.34 (10)	C36—C31—C41—C46	52.81 (12)
C11—C12—C13—C14	54.76 (14)	C32—C31—C41—C46	−71.85 (12)
C12—C13—C14—C15	−58.26 (14)	O4—C41—C42—C43	61.27 (12)
C13—C14—C15—C16	57.90 (15)	C46—C41—C42—C43	−54.06 (13)
C14—C15—C16—C11	−53.81 (14)	C31—C41—C42—C43	179.46 (9)
O1—C11—C16—C15	−69.52 (13)	C41—C42—C43—C44	57.10 (14)
C12—C11—C16—C15	47.90 (13)	C42—C43—C44—C45	−56.49 (15)
C21—C11—C16—C15	172.17 (9)	C43—C44—C45—C46	55.87 (15)
O1—C11—C21—O2	−177.82 (9)	C44—C45—C46—C41	−54.71 (14)
C16—C11—C21—O2	−59.39 (11)	O4—C41—C46—C45	−62.50 (12)
C12—C11—C21—O2	64.35 (11)	C42—C41—C46—C45	52.40 (13)
O1—C11—C21—C26	64.30 (11)	C31—C41—C46—C45	177.81 (9)
C16—C11—C21—C26	−177.27 (9)	O5—C51—C52—C53	60.10 (11)
C12—C11—C21—C26	−53.53 (12)	C56—C51—C52—C53	−54.88 (12)
O1—C11—C21—C22	−59.50 (12)	C61—C51—C52—C53	178.14 (9)
C16—C11—C21—C22	58.93 (12)	C51—C52—C53—C54	58.53 (13)
C12—C11—C21—C22	−177.33 (10)	C52—C53—C54—C55	−56.80 (14)
O2—C21—C22—C23	−69.88 (13)	C53—C54—C55—C56	54.94 (14)
C26—C21—C22—C23	47.91 (14)	C54—C55—C56—C51	−53.52 (14)
C11—C21—C22—C23	172.14 (10)	O5—C51—C56—C55	−63.46 (12)
C21—C22—C23—C24	−54.81 (15)	C52—C51—C56—C55	51.84 (13)
C22—C23—C24—C25	58.89 (15)	C61—C51—C56—C55	177.14 (10)
C23—C24—C25—C26	−58.37 (15)	O5—C51—C61—O6	55.14 (10)
O2—C21—C26—C25	70.69 (12)	C52—C51—C61—O6	−62.20 (11)
C22—C21—C26—C25	−47.43 (13)	C56—C51—C61—O6	173.61 (9)
C11—C21—C26—C25	−171.45 (10)	O5—C51—C61—C66	−62.12 (10)
C24—C25—C26—C21	53.99 (14)	C52—C51—C61—C66	−179.45 (9)
O3—C31—C32—C33	−62.96 (13)	C56—C51—C61—C66	56.35 (12)
C36—C31—C32—C33	52.04 (13)	O5—C51—C61—C62	173.45 (8)
C41—C31—C32—C33	177.62 (10)	C52—C51—C61—C62	56.11 (11)
C31—C32—C33—C34	−55.49 (15)	C56—C51—C61—C62	−68.09 (12)
C32—C33—C34—C35	56.84 (15)	O6—C61—C62—C63	−63.23 (12)
C33—C34—C35—C36	−56.50 (15)	C66—C61—C62—C63	51.86 (13)
C34—C35—C36—C31	56.00 (14)	C51—C61—C62—C63	177.42 (9)
O3—C31—C36—C35	62.11 (12)	C61—C62—C63—C64	−54.15 (14)
C32—C31—C36—C35	−52.88 (13)	C62—C63—C64—C65	55.53 (16)
C41—C31—C36—C35	−179.78 (9)	C63—C64—C65—C66	−56.49 (15)
O3—C31—C41—O4	50.95 (11)	C64—C65—C66—C61	57.40 (14)
C36—C31—C41—O4	−66.05 (11)	O6—C61—C66—C65	60.90 (12)
C32—C31—C41—O4	169.29 (9)	C62—C61—C66—C65	−54.03 (13)
O3—C31—C41—C42	−65.95 (11)	C51—C61—C66—C65	179.10 (9)
C36—C31—C41—C42	177.05 (9)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···O5	0.78	2.13	2.8182 (12)	149
O1—H1B···O4	0.77	2.08	2.8179 (11)	161
O2—H2A···O6ⁱ	0.81	2.14	2.8315 (11)	143
O2—H2B···O3ⁱ	0.71	2.23	2.8551 (12)	147
O3—H3A···O2ⁱⁱ	0.89	2.07	2.8551 (12)	148
O3—H3B···O5	0.88	1.97	2.8425 (11)	172
O4—H4A···O1	0.83	2.01	2.8179 (11)	162
O4—H4B···O5	0.79	2.59	3.1501 (12)	130
O4—H4B···O6	0.79	2.13	2.8681 (12)	157
O5—H5A···O3	0.86	1.99	2.8425 (11)	170
O5—H5B···O1	0.80	2.12	2.8182 (12)	145
O6—H6A···O4	0.84	2.04	2.8681 (12)	170
O6—H6A···O5	0.84	2.49	2.7763 (12)	101
O6—H6B···O2ⁱⁱ	0.95	1.91	2.8315 (11)	164
C12—H12A···O2	0.99	2.57	2.9683 (15)	104
C16—H16B···O2	0.99	2.49	2.9056 (15)	105
C22—H22B···O1	0.99	2.51	2.9180 (15)	105
C26—H26B···O1	0.99	2.57	2.9676 (14)	104
C42—H42B···O2ⁱⁱ	0.99	2.57	3.5090 (15)	159
C52—H52B···O2ⁱⁱ	0.99	2.58	3.5291 (14)	161
C52—H52B···O6	0.99	2.59	2.9541 (14)	102

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

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