organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoIUCrDATA
ISSN: 2414-3146

[1,1′-Bi­cyclo­hexa­ne]-1,1′-diol

crossmark logo

aNelson Mandela University, Summerstrand Campus, Department of Chemistry, University Way, Summerstrand, PO Box 77000, Port Elizabeth, 6031, South Africa
*Correspondence e-mail: richard.betz@mandela.ac.za

Edited by M. Bolte, Goethe-Universität Frankfurt, Germany (Received 10 October 2023; accepted 7 November 2023; online 14 November 2023)

This article is part of a collection of articles to commemorate the founding of the African Crystallographic Association and the 75th anniversary of the IUCr.

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.

3D view (loading...)
[Scheme 3D1]
Chemical scheme
[Scheme 1]

Structure description

Chelating ligands have found widespread use in coordination chemistry due to the increased stability of coordination compounds they can form in comparison to monodentate ligands (Gade, 1998[Gade, L. H. (1998). Koordinationschemie, 1. Auflage. Weinheim: Wiley-VCH.]). Diols are particularly inter­esting in this aspect as they offer two hydroxyl groups that – depending on the experimental conditions – can either act as fully neutral, fully anionic or mixed neutral-anionic ligands. Upon varying the substitution pattern on the hydro­carbon backbone, the acidity of the respective hydroxyl groups can be fine-tuned over a wide range and they may, thus, serve as probes for establishing the rules in which pKa range coordination to various central atoms can be observed. Furthermore, the steric pretence of potential substituents may give rise to unique coordination and bonding patterns. To allow for comparisons of metrical parameters of the title compound in envisioned coordination compounds, the crystal and mol­ecular structure of the free ligand was determined. The crystal structures of the related pinacols derived from cyclo­penta­none (Hosten & Betz, 2021[Hosten, E. C. & Betz, R. (2021). Z. Krist. New Cryst. Struct. 236, 197-199.]), cyclo­hepta­none (Betz & Klüfers, 2007[Betz, R. & Klüfers, P. (2007). Acta Cryst. E63, o4752.]) and cyclo­dodeca­none (Yang et al., 2016[Yang, M., Zhang, X., Wang, M. & Wang, M. (2016). Chin. J. Org. Chem. 36, 399-405.]) are apparent in the literature. Structural data of symmetric pinacols derived from methyl-substituted (Bruss et al., 1987[Bruss, D. R., Larsen, R., Walsh, R. J., Fait, J., Mundy, B. P., Ekeland, R. A. & Fitzgerald, A. (1987). Acta Cryst. C43, 1932-1936.]) and phenyl-substituted cyclo­hexa­nones (Nieger et al., 2004[Nieger, M., Herold, D. & Vogtle, F. (2004). CSD Communication (refcode YAFNID) CCDC, Cambridge, England.]) have been reported. Furthermore, metrical information based on diffraction studies of other sterically demanding diols such as 1,2-di-tert-butyl-ethane-1,2-diol (Kerscher et al., 2009[Kerscher, T., Betz, R., Klüfers, P. & Mayer, P. (2009). Acta Cryst. E65, o211.]), 1,2-di­cyclo­pentyl-ethane-1,2-diol (Betz et al., 2007[Betz, R., Herdlicka, S. & Klüfers, P. (2007). Acta Cryst. E63, o3986.]), as well as cis-1,2-dimethyl-cyclo­butane-1,2-diol (Allscher et al., 2008[Allscher, T., Betz, R., Herdlicka, S. & Klüfers, P. (2008). Acta Cryst. C64, o111-o113.]) are available. The crystal and mol­ecular structure of a coordination compound of osmium featuring the title compound as chelating ligand is apparent in the literature (Lehtonen et al., 1999[Lehtonen, A., Jokela, J., Edwards, P. G. & Sillanpää, R. (1999). J. Chem. Soc. Dalton Trans. pp. 2785-2788.]).

The asymmetric unit of the title compound is shown in Fig. 1[link] and contains three complete mol­ecules. Bond lengths and angles are normal and in good agreement with values reported for other symmetric pinacols. The hydrogen atoms of the hydroxyl groups are disordered over two orientations. A conformational analysis of the cyclo­hexane rings (Cremer & Pople, 1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1375-1358.]) shows the latter to invariably adopt chair conformations (Boeyens, 1978[Boeyens, J. C. A. (1978). J. Cryst. Mol. Struct. 8, 317-320.]) with each of the three mol­ecules featuring one ring in a 1C4 and the second ring in a 4C1 conformation. In two of the three mol­ecules, the hydroxyl groups adopt a somewhat staggered conformation with respective O—C—C—O torsion angles of 50.95 (11) and 55.14 (10)°, while in the third mol­ecule the two alcoholic groups are arranged in an almost perfect anti conformation with the pertaining O—C—C—O angle measuring −177.82 (9)°.

[Figure 1]
Figure 1
The mol­ecular structure of the title compound, with atom labels and anisotropic displacement ellipsoids (drawn at the 50% probability level). For clarity, only one of the two disordered hydrogen-atom positions is depicted.

In the crystal, classical hydrogen bonds of the O—H⋯O type are apparent that involve all hydroxyl groups as donors and acceptors (Table 1[link]), forming cooperative cyclic patterns. In terms of graph-set analysis (Etter et al., 1990[Etter, M. C., MacDonald, J. C. & Bernstein, J. (1990). Acta Cryst. B46, 256-262.]; Bernstein et al., 1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]), the descriptor for these hydrogen bonds is DDDDDD on the unary level while an R66(12) descriptor is required on the hexa­nary level. The mol­ecule featuring the anti-orientated hydroxyl groups acts as a linker between these various trimeric arrangements, thus giving rise to infinite chains of the hitherto hydrogen-bonded mol­ecules along the crystallographic a-axis direction. A depiction of the pattern is shown in Fig. 2[link].

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA 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].
[Figure 2]
Figure 2
Inter­molecular contacts, viewed approximately along [011]. For clarity, only one of the two disordered hydrogen-atom positions is depicted.

Synthesis and crystallization

The title compound was synthesized from cyclo­hexa­none according to a published procedure (Criegee et al., 1952[Criegee, R., Vogel, E. & Höger, H. (1952). Chem. Ber. 85, 144-152.]). Crystals suitable for the diffraction study were obtained upon slow evaporation of a solution of the compound in THF at room temperature.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2[link]. The carbon-bound H atoms of the methyl­ene groups were placed in calculated positions (C–H 0.99 Å) and were included in the refinement in the riding model approximation, with Uiso(H) set to 1.2Ueq(C). The H atoms of the hydroxyl groups were located in a DFM accounting for the equal disorder over two positions, with Uiso(H) set to 1.5Ueq(O).

Table 2
Experimental details

Crystal data
Chemical formula C12H22O2
Mr 198.29
Crystal system, space group Triclinic, P[\overline{1}]
Temperature (K) 200
a, b, c (Å) 9.8996 (7), 10.0299 (7), 17.9841 (13)
α, β, γ (°) 73.810 (3), 86.774 (4), 83.592 (3)
V3) 1703.6 (2)
Z 6
Radiation type Mo Kα
μ (mm−1) 0.08
Crystal size (mm) 0.60 × 0.49 × 0.18
 
Data collection
Diffractometer Bruker APEXII CCD
Absorption correction Numerical (SADABS; Krause et al., 2015[Krause, L., Herbst-Irmer, R., Sheldrick, G. M. & Stalke, D. (2015). J. Appl. Cryst. 48, 3-10.])
Tmin, Tmax 0.941, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections 30730, 8498, 6202
Rint 0.024
(sin θ/λ)max−1) 0.669
 
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.042, 0.110, 1.02
No. of reflections 8498
No. of parameters 380
H-atom treatment H-atom parameters constrained
Δρmax, Δρmin (e Å−3) 0.29, −0.19
Computer programs: APEX2 and SAINT (Bruker, 2010[Bruker (2010). APEX2 and SAINT. Bruker AXS Inc., Madison, USA.]), SHELXS97 and SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]), PLATON (Spek, 2020[Spek, A. L. (2020). Acta Cryst. E76, 1-11.]), Mercury (Macrae et al., 2020[Macrae, C. F., Sovago, I., Cottrell, S. J., Galek, P. T. A., McCabe, P., Pidcock, E., Platings, M., Shields, G. P., Stevens, J. S., Towler, M. & Wood, P. A. (2020). J. Appl. Cryst. 53, 226-235.]) and SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]).

Structural data


Computing details top

[1,1'-Bicyclohexane]-1,1'-diol top
Crystal data top
C12H22O2Z = 6
Mr = 198.29F(000) = 660
Triclinic, P1Dx = 1.160 Mg m3
a = 9.8996 (7) ÅMo Kα radiation, λ = 0.71073 Å
b = 10.0299 (7) ÅCell parameters from 9559 reflections
c = 17.9841 (13) Åθ = 2.4–28.3°
α = 73.810 (3)°µ = 0.08 mm1
β = 86.774 (4)°T = 200 K
γ = 83.592 (3)°Blocks, colourless
V = 1703.6 (2) Å30.60 × 0.49 × 0.18 mm
Data collection top
Bruker APEXII CCD
diffractometer
8498 independent reflections
Radiation source: sealed tube6202 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.024
φ and ω scansθmax = 28.4°, θmin = 2.1°
Absorption correction: numerical
(SADABS; Krause et al., 2015)
h = 1313
Tmin = 0.941, Tmax = 1.000k = 1313
30730 measured reflectionsl = 2324
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.042Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.110H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.0505P)2 + 0.3176P]
where P = (Fo2 + 2Fc2)/3
8498 reflections(Δ/σ)max = 0.001
380 parametersΔρmax = 0.29 e Å3
0 restraintsΔρmin = 0.19 e Å3
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
xyzUiso*/UeqOcc. (<1)
O10.56808 (8)0.29971 (10)0.76040 (6)0.0365 (2)
H1A0.5157940.3616120.7413100.055*0.5
H1B0.5230940.2395160.7780100.055*0.5
O20.93801 (8)0.22716 (9)0.73920 (6)0.0348 (2)
H2A0.9883460.2217030.7030670.052*0.5
H2B0.9639460.2399030.7723660.052*0.5
O30.14540 (8)0.28120 (8)0.82788 (4)0.02719 (19)
H3A0.0782910.2377340.8176630.041*0.5
H3B0.1982910.3214340.7892540.027*0.5
O40.36472 (8)0.11455 (8)0.79255 (5)0.02812 (19)
H4A0.4352440.1542970.7886660.042*0.5
H4B0.3320440.1652970.7548660.042*0.5
O50.31219 (8)0.43533 (8)0.70791 (5)0.02771 (19)
H5A0.2689100.3805440.7445710.042*0.5
H5B0.3939100.4237440.7060710.042*0.5
O60.19507 (8)0.23358 (8)0.66154 (5)0.02741 (19)
H6A0.2433950.2081540.7009160.041*0.5
H6B0.1019600.2342540.6780210.041*0.5
C110.70830 (10)0.32190 (11)0.76342 (6)0.0201 (2)
C120.72690 (12)0.46897 (12)0.71186 (7)0.0286 (3)
H12A0.8253540.4798290.7047900.034*
H12B0.6903090.4791390.6602470.034*
C130.65728 (14)0.58557 (14)0.74410 (9)0.0384 (3)
H13A0.6794330.6769500.7100340.046*
H13B0.5574720.5834940.7447010.046*
C140.70274 (14)0.56951 (15)0.82538 (9)0.0405 (3)
H14A0.6551530.6449610.8455330.049*
H14B0.8017030.5770720.8245560.049*
C150.67119 (14)0.42892 (15)0.87778 (8)0.0374 (3)
H15A0.5715770.4243480.8811470.045*
H15B0.7028730.4184940.9305300.045*
C160.73978 (13)0.30961 (13)0.84762 (7)0.0304 (3)
H16A0.7104960.2205700.8809100.037*
H16B0.8394110.3060660.8521290.037*
C210.79768 (10)0.20756 (11)0.73319 (6)0.0195 (2)
C220.77309 (13)0.06019 (12)0.78313 (7)0.0305 (3)
H22A0.8068320.0472270.8357120.037*
H22B0.6739760.0524340.7880160.037*
C230.84177 (14)0.05635 (13)0.75082 (8)0.0367 (3)
H23A0.9417110.0574870.7523240.044*
H23B0.8159500.1473370.7835470.044*
C240.80068 (15)0.03633 (14)0.66817 (9)0.0403 (3)
H24A0.8469540.1124720.6481140.048*
H24B0.7012940.0394650.6666760.048*
C250.83963 (14)0.10308 (15)0.61805 (8)0.0374 (3)
H25A0.8117170.1164170.5642500.045*
H25B0.9396340.1035750.6174250.045*
C260.77213 (12)0.22312 (13)0.64813 (7)0.0273 (3)
H26A0.8058020.3111910.6164240.033*
H26B0.6728440.2306450.6410550.033*
C310.21725 (11)0.18418 (11)0.89152 (6)0.0200 (2)
C320.11161 (12)0.14108 (13)0.95726 (7)0.0301 (3)
H32A0.0386650.0994710.9386460.036*
H32B0.1556020.0689011.0008630.036*
C330.04866 (13)0.26421 (15)0.98627 (8)0.0373 (3)
H33A0.0047500.3313000.9445000.045*
H33B0.0143160.2301731.0305800.045*
C340.15628 (14)0.33828 (16)1.01140 (8)0.0386 (3)
H34A0.2046890.2740071.0562360.046*
H34B0.1123170.4196621.0276320.046*
C350.25723 (13)0.38674 (13)0.94504 (8)0.0325 (3)
H35A0.3292640.4308540.9627450.039*
H35B0.2100610.4574590.9020400.039*
C360.32149 (11)0.26445 (12)0.91615 (7)0.0256 (2)
H36A0.3769000.1994150.9577380.031*
H36B0.3833350.2999100.8714990.031*
C410.28844 (11)0.05912 (11)0.86257 (6)0.0204 (2)
C420.18433 (12)0.02606 (12)0.84183 (7)0.0278 (3)
H42A0.1265050.0627420.8881780.033*
H42B0.1247840.0361530.8013330.033*
C430.25017 (14)0.14774 (13)0.81273 (8)0.0358 (3)
H43A0.1785830.2009250.8020820.043*
H43B0.3015250.1113650.7637250.043*
C440.34571 (15)0.24392 (13)0.87229 (9)0.0387 (3)
H44A0.3908100.3195010.8513730.046*
H44B0.2931210.2870810.9197070.046*
C450.45267 (14)0.16253 (13)0.89230 (8)0.0359 (3)
H45A0.5111920.1281250.8459250.043*
H45B0.5109170.2256320.9331670.043*
C460.38887 (13)0.03865 (13)0.92049 (7)0.0301 (3)
H46A0.4618860.0148680.9290860.036*
H46B0.3405970.0739310.9707040.036*
C510.24752 (10)0.47484 (11)0.63405 (6)0.0207 (2)
C520.09989 (11)0.52910 (12)0.64770 (7)0.0245 (2)
H52A0.0518960.5550350.5980910.029*
H52B0.0540600.4533450.6842570.029*
C530.08875 (13)0.65513 (13)0.68017 (7)0.0301 (3)
H53A0.0082950.6865940.6873080.036*
H53B0.1314660.6283970.7313960.036*
C540.15860 (13)0.77386 (13)0.62562 (8)0.0343 (3)
H54A0.1541090.8533020.6485510.041*
H54B0.1111700.8060440.5757890.041*
C550.30656 (13)0.72491 (13)0.61147 (8)0.0353 (3)
H55A0.3558790.7040910.6604200.042*
H55B0.3488640.8011600.5731650.042*
C560.32183 (12)0.59495 (13)0.58173 (7)0.0294 (3)
H56A0.4196450.5628440.5782490.035*
H56B0.2854120.6198870.5289350.035*
C610.25485 (10)0.34261 (12)0.60330 (6)0.0209 (2)
C620.17544 (12)0.36547 (13)0.52915 (7)0.0280 (3)
H62A0.0780560.3901710.5398220.034*
H62B0.2086410.4449560.4887520.034*
C630.18968 (13)0.23674 (15)0.49851 (8)0.0352 (3)
H63A0.1443200.1612080.5355470.042*
H63B0.1430720.2597950.4485690.042*
C640.33798 (14)0.18484 (16)0.48677 (8)0.0391 (3)
H64A0.3426350.0980890.4702990.047*
H64B0.3812970.2558160.4454470.047*
C650.41386 (13)0.15677 (15)0.56150 (8)0.0353 (3)
H65A0.5108630.1274990.5525760.042*
H65B0.3756630.0798190.6014390.042*
C660.40235 (11)0.28693 (14)0.59025 (7)0.0283 (3)
H66A0.4477450.3608030.5519630.034*
H66B0.4508760.2650980.6395240.034*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0136 (4)0.0469 (6)0.0588 (6)0.0060 (4)0.0016 (4)0.0298 (5)
O20.0141 (4)0.0387 (5)0.0583 (6)0.0014 (3)0.0053 (4)0.0238 (4)
O30.0292 (4)0.0283 (4)0.0214 (4)0.0039 (3)0.0054 (3)0.0041 (3)
O40.0303 (4)0.0261 (4)0.0248 (4)0.0019 (3)0.0046 (3)0.0031 (3)
O50.0307 (4)0.0289 (4)0.0224 (4)0.0032 (3)0.0099 (3)0.0032 (3)
O60.0322 (4)0.0269 (4)0.0224 (4)0.0062 (3)0.0028 (3)0.0049 (3)
C110.0134 (5)0.0236 (5)0.0237 (5)0.0030 (4)0.0018 (4)0.0068 (4)
C120.0285 (6)0.0220 (6)0.0339 (6)0.0021 (5)0.0011 (5)0.0060 (5)
C130.0366 (7)0.0257 (7)0.0540 (9)0.0016 (5)0.0029 (6)0.0142 (6)
C140.0332 (7)0.0404 (8)0.0595 (9)0.0046 (6)0.0007 (6)0.0323 (7)
C150.0332 (7)0.0497 (8)0.0378 (7)0.0039 (6)0.0011 (6)0.0266 (6)
C160.0319 (6)0.0357 (7)0.0258 (6)0.0004 (5)0.0023 (5)0.0127 (5)
C210.0133 (5)0.0227 (5)0.0230 (5)0.0023 (4)0.0023 (4)0.0066 (4)
C220.0346 (6)0.0224 (6)0.0320 (6)0.0028 (5)0.0004 (5)0.0037 (5)
C230.0400 (7)0.0225 (6)0.0479 (8)0.0022 (5)0.0084 (6)0.0107 (6)
C240.0390 (7)0.0350 (7)0.0544 (9)0.0052 (6)0.0131 (6)0.0258 (7)
C250.0381 (7)0.0459 (8)0.0327 (7)0.0054 (6)0.0043 (6)0.0211 (6)
C260.0273 (6)0.0307 (6)0.0245 (6)0.0022 (5)0.0043 (5)0.0096 (5)
C310.0200 (5)0.0220 (5)0.0174 (5)0.0045 (4)0.0033 (4)0.0030 (4)
C320.0308 (6)0.0334 (7)0.0259 (6)0.0116 (5)0.0050 (5)0.0055 (5)
C330.0333 (7)0.0467 (8)0.0339 (7)0.0088 (6)0.0116 (5)0.0149 (6)
C340.0420 (7)0.0470 (8)0.0325 (7)0.0024 (6)0.0015 (6)0.0215 (6)
C350.0337 (6)0.0318 (7)0.0379 (7)0.0071 (5)0.0035 (5)0.0172 (5)
C360.0231 (5)0.0305 (6)0.0263 (6)0.0070 (5)0.0026 (4)0.0110 (5)
C410.0212 (5)0.0202 (5)0.0191 (5)0.0043 (4)0.0039 (4)0.0025 (4)
C420.0269 (6)0.0230 (6)0.0344 (6)0.0051 (5)0.0087 (5)0.0069 (5)
C430.0387 (7)0.0278 (6)0.0465 (8)0.0048 (5)0.0130 (6)0.0164 (6)
C440.0456 (8)0.0222 (6)0.0478 (8)0.0008 (6)0.0074 (6)0.0091 (6)
C450.0379 (7)0.0282 (7)0.0399 (7)0.0069 (5)0.0160 (6)0.0077 (6)
C460.0344 (6)0.0276 (6)0.0279 (6)0.0010 (5)0.0127 (5)0.0061 (5)
C510.0169 (5)0.0250 (6)0.0178 (5)0.0011 (4)0.0032 (4)0.0016 (4)
C520.0184 (5)0.0263 (6)0.0276 (6)0.0000 (4)0.0014 (4)0.0060 (5)
C530.0290 (6)0.0286 (6)0.0325 (6)0.0009 (5)0.0008 (5)0.0094 (5)
C540.0400 (7)0.0252 (6)0.0362 (7)0.0019 (5)0.0056 (6)0.0060 (5)
C550.0360 (7)0.0294 (7)0.0380 (7)0.0108 (5)0.0008 (6)0.0025 (5)
C560.0265 (6)0.0310 (6)0.0265 (6)0.0056 (5)0.0023 (5)0.0003 (5)
C610.0156 (5)0.0271 (6)0.0182 (5)0.0001 (4)0.0011 (4)0.0038 (4)
C620.0237 (5)0.0370 (7)0.0232 (6)0.0034 (5)0.0064 (4)0.0094 (5)
C630.0309 (6)0.0469 (8)0.0321 (7)0.0050 (6)0.0098 (5)0.0196 (6)
C640.0362 (7)0.0531 (9)0.0330 (7)0.0083 (6)0.0047 (6)0.0246 (6)
C650.0266 (6)0.0467 (8)0.0343 (7)0.0107 (6)0.0036 (5)0.0189 (6)
C660.0171 (5)0.0435 (7)0.0247 (6)0.0029 (5)0.0018 (4)0.0119 (5)
Geometric parameters (Å, º) top
O1—C111.4366 (12)C33—H33B0.9900
O1—H1A0.7750C34—C351.5199 (18)
O1—H1B0.7750C34—H34A0.9900
O2—C211.4387 (12)C34—H34B0.9900
O2—H2A0.8069C35—C361.5242 (17)
O2—H2B0.7106C35—H35A0.9900
O3—C311.4418 (13)C35—H35B0.9900
O3—H3A0.8879C36—H36A0.9900
O3—H3B0.8772C36—H36B0.9900
O4—C411.4357 (12)C41—C421.5325 (15)
O4—H4A0.8321C41—C461.5377 (16)
O4—H4B0.7865C42—C431.5259 (18)
O5—C511.4412 (13)C42—H42A0.9900
O5—H5A0.8596C42—H42B0.9900
O5—H5B0.8045C43—C441.5187 (19)
O6—C611.4419 (12)C43—H43A0.9900
O6—H6A0.8399C43—H43B0.9900
O6—H6B0.9521C44—C451.5220 (19)
C11—C161.5317 (16)C44—H44A0.9900
C11—C121.5324 (15)C44—H44B0.9900
C11—C211.5685 (15)C45—C461.5296 (18)
C12—C131.5270 (18)C45—H45A0.9900
C12—H12A0.9900C45—H45B0.9900
C12—H12B0.9900C46—H46A0.9900
C13—C141.514 (2)C46—H46B0.9900
C13—H13A0.9900C51—C521.5326 (15)
C13—H13B0.9900C51—C561.5380 (15)
C14—C151.516 (2)C51—C611.5662 (16)
C14—H14A0.9900C52—C531.5246 (17)
C14—H14B0.9900C52—H52A0.9900
C15—C161.5252 (18)C52—H52B0.9900
C15—H15A0.9900C53—C541.5214 (17)
C15—H15B0.9900C53—H53A0.9900
C16—H16A0.9900C53—H53B0.9900
C16—H16B0.9900C54—C551.5226 (18)
C21—C261.5265 (16)C54—H54A0.9900
C21—C221.5382 (15)C54—H54B0.9900
C22—C231.5241 (18)C55—C561.5309 (18)
C22—H22A0.9900C55—H55A0.9900
C22—H22B0.9900C55—H55B0.9900
C23—C241.516 (2)C56—H56A0.9900
C23—H23A0.9900C56—H56B0.9900
C23—H23B0.9900C61—C661.5335 (15)
C24—C251.515 (2)C61—C621.5350 (16)
C24—H24A0.9900C62—C631.5290 (18)
C24—H24B0.9900C62—H62A0.9900
C25—C261.5270 (18)C62—H62B0.9900
C25—H25A0.9900C63—C641.5254 (18)
C25—H25B0.9900C63—H63A0.9900
C26—H26A0.9900C63—H63B0.9900
C26—H26B0.9900C64—C651.5183 (18)
C31—C361.5314 (15)C64—H64A0.9900
C31—C321.5346 (14)C64—H64B0.9900
C31—C411.5705 (16)C65—C661.5236 (18)
C32—C331.5287 (18)C65—H65A0.9900
C32—H32A0.9900C65—H65B0.9900
C32—H32B0.9900C66—H66A0.9900
C33—C341.5196 (19)C66—H66B0.9900
C33—H33A0.9900
C11—O1—H1A120.0C34—C35—H35B109.5
C11—O1—H1B136.4C36—C35—H35B109.5
H1A—O1—H1B103.2H35A—C35—H35B108.1
C21—O2—H2A117.1C35—C36—C31113.42 (10)
C21—O2—H2B123.0C35—C36—H36A108.9
H2A—O2—H2B119.9C31—C36—H36A108.9
C31—O3—H3A106.4C35—C36—H36B108.9
C31—O3—H3B114.1C31—C36—H36B108.9
H3A—O3—H3B118.1H36A—C36—H36B107.7
C41—O4—H4A126.5O4—C41—C42106.37 (9)
C41—O4—H4B123.6O4—C41—C46107.05 (9)
H4A—O4—H4B95.3C42—C41—C46109.45 (9)
C51—O5—H5A114.5O4—C41—C31108.51 (8)
C51—O5—H5B115.3C42—C41—C31111.61 (9)
H5A—O5—H5B118.9C46—C41—C31113.48 (9)
C61—O6—H6A109.8C43—C42—C41112.97 (10)
C61—O6—H6B126.1C43—C42—H42A109.0
H6A—O6—H6B108.6C41—C42—H42A109.0
O1—C11—C16108.21 (9)C43—C42—H42B109.0
O1—C11—C12107.43 (9)C41—C42—H42B109.0
C16—C11—C12110.59 (10)H42A—C42—H42B107.8
O1—C11—C21108.01 (9)C44—C43—C42110.78 (11)
C16—C11—C21110.92 (9)C44—C43—H43A109.5
C12—C11—C21111.52 (8)C42—C43—H43A109.5
C13—C12—C11113.94 (10)C44—C43—H43B109.5
C13—C12—H12A108.8C42—C43—H43B109.5
C11—C12—H12A108.8H43A—C43—H43B108.1
C13—C12—H12B108.8C43—C44—C45110.29 (11)
C11—C12—H12B108.8C43—C44—H44A109.6
H12A—C12—H12B107.7C45—C44—H44A109.6
C14—C13—C12111.01 (11)C43—C44—H44B109.6
C14—C13—H13A109.4C45—C44—H44B109.6
C12—C13—H13A109.4H44A—C44—H44B108.1
C14—C13—H13B109.4C44—C45—C46112.07 (11)
C12—C13—H13B109.4C44—C45—H45A109.2
H13A—C13—H13B108.0C46—C45—H45A109.2
C13—C14—C15109.87 (11)C44—C45—H45B109.2
C13—C14—H14A109.7C46—C45—H45B109.2
C15—C14—H14A109.7H45A—C45—H45B107.9
C13—C14—H14B109.7C45—C46—C41112.44 (10)
C15—C14—H14B109.7C45—C46—H46A109.1
H14A—C14—H14B108.2C41—C46—H46A109.1
C14—C15—C16111.40 (11)C45—C46—H46B109.1
C14—C15—H15A109.3C41—C46—H46B109.1
C16—C15—H15A109.3H46A—C46—H46B107.8
C14—C15—H15B109.3O5—C51—C52107.05 (9)
C16—C15—H15B109.3O5—C51—C56106.55 (9)
H15A—C15—H15B108.0C52—C51—C56109.20 (9)
C15—C16—C11114.03 (11)O5—C51—C61108.20 (8)
C15—C16—H16A108.7C52—C51—C61111.28 (9)
C11—C16—H16A108.7C56—C51—C61114.21 (9)
C15—C16—H16B108.7C53—C52—C51112.79 (10)
C11—C16—H16B108.7C53—C52—H52A109.0
H16A—C16—H16B107.6C51—C52—H52A109.0
O2—C21—C26107.70 (9)C53—C52—H52B109.0
O2—C21—C22108.24 (9)C51—C52—H52B109.0
C26—C21—C22110.64 (10)H52A—C52—H52B107.8
O2—C21—C11107.67 (8)C54—C53—C52110.60 (10)
C26—C21—C11111.40 (9)C54—C53—H53A109.5
C22—C21—C11111.03 (9)C52—C53—H53A109.5
C23—C22—C21113.89 (10)C54—C53—H53B109.5
C23—C22—H22A108.8C52—C53—H53B109.5
C21—C22—H22A108.8H53A—C53—H53B108.1
C23—C22—H22B108.8C53—C54—C55110.03 (10)
C21—C22—H22B108.8C53—C54—H54A109.7
H22A—C22—H22B107.7C55—C54—H54A109.7
C24—C23—C22111.02 (11)C53—C54—H54B109.7
C24—C23—H23A109.4C55—C54—H54B109.7
C22—C23—H23A109.4H54A—C54—H54B108.2
C24—C23—H23B109.4C54—C55—C56112.60 (11)
C22—C23—H23B109.4C54—C55—H55A109.1
H23A—C23—H23B108.0C56—C55—H55A109.1
C25—C24—C23109.52 (11)C54—C55—H55B109.1
C25—C24—H24A109.8C56—C55—H55B109.1
C23—C24—H24A109.8H55A—C55—H55B107.8
C25—C24—H24B109.8C55—C56—C51112.75 (10)
C23—C24—H24B109.8C55—C56—H56A109.0
H24A—C24—H24B108.2C51—C56—H56A109.0
C24—C25—C26111.29 (11)C55—C56—H56B109.0
C24—C25—H25A109.4C51—C56—H56B109.0
C26—C25—H25A109.4H56A—C56—H56B107.8
C24—C25—H25B109.4O6—C61—C66106.78 (9)
C26—C25—H25B109.4O6—C61—C62106.53 (9)
H25A—C25—H25B108.0C66—C61—C62109.43 (9)
C21—C26—C25114.23 (10)O6—C61—C51108.35 (8)
C21—C26—H26A108.7C66—C61—C51111.55 (9)
C25—C26—H26A108.7C62—C61—C51113.83 (9)
C21—C26—H26B108.7C63—C62—C61112.64 (10)
C25—C26—H26B108.7C63—C62—H62A109.1
H26A—C26—H26B107.6C61—C62—H62A109.1
O3—C31—C36106.58 (9)C63—C62—H62B109.1
O3—C31—C32106.55 (9)C61—C62—H62B109.1
C36—C31—C32109.71 (9)H62A—C62—H62B107.8
O3—C31—C41108.42 (8)C64—C63—C62112.29 (11)
C36—C31—C41111.44 (9)C64—C63—H63A109.1
C32—C31—C41113.76 (9)C62—C63—H63A109.1
C33—C32—C31112.37 (10)C64—C63—H63B109.1
C33—C32—H32A109.1C62—C63—H63B109.1
C31—C32—H32A109.1H63A—C63—H63B107.9
C33—C32—H32B109.1C65—C64—C63110.19 (10)
C31—C32—H32B109.1C65—C64—H64A109.6
H32A—C32—H32B107.9C63—C64—H64A109.6
C34—C33—C32111.83 (11)C65—C64—H64B109.6
C34—C33—H33A109.3C63—C64—H64B109.6
C32—C33—H33A109.3H64A—C64—H64B108.1
C34—C33—H33B109.3C64—C65—C66110.68 (11)
C32—C33—H33B109.3C64—C65—H65A109.5
H33A—C33—H33B107.9C66—C65—H65A109.5
C33—C34—C35110.14 (11)C64—C65—H65B109.5
C33—C34—H34A109.6C66—C65—H65B109.5
C35—C34—H34A109.6H65A—C65—H65B108.1
C33—C34—H34B109.6C65—C66—C61113.16 (10)
C35—C34—H34B109.6C65—C66—H66A108.9
H34A—C34—H34B108.1C61—C66—H66A108.9
C34—C35—C36110.82 (10)C65—C66—H66B108.9
C34—C35—H35A109.5C61—C66—H66B108.9
C36—C35—H35A109.5H66A—C66—H66B107.8
O1—C11—C12—C1369.48 (13)C32—C31—C41—C4252.39 (12)
C16—C11—C12—C1348.41 (13)O3—C31—C41—C46169.81 (9)
C21—C11—C12—C13172.34 (10)C36—C31—C41—C4652.81 (12)
C11—C12—C13—C1454.76 (14)C32—C31—C41—C4671.85 (12)
C12—C13—C14—C1558.26 (14)O4—C41—C42—C4361.27 (12)
C13—C14—C15—C1657.90 (15)C46—C41—C42—C4354.06 (13)
C14—C15—C16—C1153.81 (14)C31—C41—C42—C43179.46 (9)
O1—C11—C16—C1569.52 (13)C41—C42—C43—C4457.10 (14)
C12—C11—C16—C1547.90 (13)C42—C43—C44—C4556.49 (15)
C21—C11—C16—C15172.17 (9)C43—C44—C45—C4655.87 (15)
O1—C11—C21—O2177.82 (9)C44—C45—C46—C4154.71 (14)
C16—C11—C21—O259.39 (11)O4—C41—C46—C4562.50 (12)
C12—C11—C21—O264.35 (11)C42—C41—C46—C4552.40 (13)
O1—C11—C21—C2664.30 (11)C31—C41—C46—C45177.81 (9)
C16—C11—C21—C26177.27 (9)O5—C51—C52—C5360.10 (11)
C12—C11—C21—C2653.53 (12)C56—C51—C52—C5354.88 (12)
O1—C11—C21—C2259.50 (12)C61—C51—C52—C53178.14 (9)
C16—C11—C21—C2258.93 (12)C51—C52—C53—C5458.53 (13)
C12—C11—C21—C22177.33 (10)C52—C53—C54—C5556.80 (14)
O2—C21—C22—C2369.88 (13)C53—C54—C55—C5654.94 (14)
C26—C21—C22—C2347.91 (14)C54—C55—C56—C5153.52 (14)
C11—C21—C22—C23172.14 (10)O5—C51—C56—C5563.46 (12)
C21—C22—C23—C2454.81 (15)C52—C51—C56—C5551.84 (13)
C22—C23—C24—C2558.89 (15)C61—C51—C56—C55177.14 (10)
C23—C24—C25—C2658.37 (15)O5—C51—C61—O655.14 (10)
O2—C21—C26—C2570.69 (12)C52—C51—C61—O662.20 (11)
C22—C21—C26—C2547.43 (13)C56—C51—C61—O6173.61 (9)
C11—C21—C26—C25171.45 (10)O5—C51—C61—C6662.12 (10)
C24—C25—C26—C2153.99 (14)C52—C51—C61—C66179.45 (9)
O3—C31—C32—C3362.96 (13)C56—C51—C61—C6656.35 (12)
C36—C31—C32—C3352.04 (13)O5—C51—C61—C62173.45 (8)
C41—C31—C32—C33177.62 (10)C52—C51—C61—C6256.11 (11)
C31—C32—C33—C3455.49 (15)C56—C51—C61—C6268.09 (12)
C32—C33—C34—C3556.84 (15)O6—C61—C62—C6363.23 (12)
C33—C34—C35—C3656.50 (15)C66—C61—C62—C6351.86 (13)
C34—C35—C36—C3156.00 (14)C51—C61—C62—C63177.42 (9)
O3—C31—C36—C3562.11 (12)C61—C62—C63—C6454.15 (14)
C32—C31—C36—C3552.88 (13)C62—C63—C64—C6555.53 (16)
C41—C31—C36—C35179.78 (9)C63—C64—C65—C6656.49 (15)
O3—C31—C41—O450.95 (11)C64—C65—C66—C6157.40 (14)
C36—C31—C41—O466.05 (11)O6—C61—C66—C6560.90 (12)
C32—C31—C41—O4169.29 (9)C62—C61—C66—C6554.03 (13)
O3—C31—C41—C4265.95 (11)C51—C61—C66—C65179.10 (9)
C36—C31—C41—C42177.05 (9)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1A···O50.782.132.8182 (12)149
O1—H1B···O40.772.082.8179 (11)161
O2—H2A···O6i0.812.142.8315 (11)143
O2—H2B···O3i0.712.232.8551 (12)147
O3—H3A···O2ii0.892.072.8551 (12)148
O3—H3B···O50.881.972.8425 (11)172
O4—H4A···O10.832.012.8179 (11)162
O4—H4B···O50.792.593.1501 (12)130
O4—H4B···O60.792.132.8681 (12)157
O5—H5A···O30.861.992.8425 (11)170
O5—H5B···O10.802.122.8182 (12)145
O6—H6A···O40.842.042.8681 (12)170
O6—H6A···O50.842.492.7763 (12)101
O6—H6B···O2ii0.951.912.8315 (11)164
C12—H12A···O20.992.572.9683 (15)104
C16—H16B···O20.992.492.9056 (15)105
C22—H22B···O10.992.512.9180 (15)105
C26—H26B···O10.992.572.9676 (14)104
C42—H42B···O2ii0.992.573.5090 (15)159
C52—H52B···O2ii0.992.583.5291 (14)161
C52—H52B···O60.992.592.9541 (14)102
Symmetry codes: (i) x+1, y, z; (ii) x1, y, z.
 

Acknowledgements

The authors thank Mr Matthias Schmidt for useful discussions.

References

First citationAllscher, T., Betz, R., Herdlicka, S. & Klüfers, P. (2008). Acta Cryst. C64, o111–o113.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationBernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573.  CrossRef CAS Web of Science Google Scholar
First citationBetz, R., Herdlicka, S. & Klüfers, P. (2007). Acta Cryst. E63, o3986.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationBetz, R. & Klüfers, P. (2007). Acta Cryst. E63, o4752.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationBoeyens, J. C. A. (1978). J. Cryst. Mol. Struct. 8, 317–320.  CrossRef Web of Science Google Scholar
First citationBruker (2010). APEX2 and SAINT. Bruker AXS Inc., Madison, USA.  Google Scholar
First citationBruss, D. R., Larsen, R., Walsh, R. J., Fait, J., Mundy, B. P., Ekeland, R. A. & Fitzgerald, A. (1987). Acta Cryst. C43, 1932–1936.  CSD CrossRef CAS Web of Science IUCr Journals Google Scholar
First citationCremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1375–1358.  Google Scholar
First citationCriegee, R., Vogel, E. & Höger, H. (1952). Chem. Ber. 85, 144–152.  CrossRef CAS Web of Science Google Scholar
First citationEtter, M. C., MacDonald, J. C. & Bernstein, J. (1990). Acta Cryst. B46, 256–262.  CrossRef ICSD CAS Web of Science IUCr Journals Google Scholar
First citationGade, L. H. (1998). Koordinationschemie, 1. Auflage. Weinheim: Wiley-VCH.  Google Scholar
First citationHosten, E. C. & Betz, R. (2021). Z. Krist. New Cryst. Struct. 236, 197–199.  CAS Google Scholar
First citationKerscher, T., Betz, R., Klüfers, P. & Mayer, P. (2009). Acta Cryst. E65, o211.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationKrause, L., Herbst-Irmer, R., Sheldrick, G. M. & Stalke, D. (2015). J. Appl. Cryst. 48, 3–10.  Web of Science CSD CrossRef ICSD CAS IUCr Journals Google Scholar
First citationLehtonen, A., Jokela, J., Edwards, P. G. & Sillanpää, R. (1999). J. Chem. Soc. Dalton Trans. pp. 2785–2788.  Web of Science CSD CrossRef Google Scholar
First citationMacrae, C. F., Sovago, I., Cottrell, S. J., Galek, P. T. A., McCabe, P., Pidcock, E., Platings, M., Shields, G. P., Stevens, J. S., Towler, M. & Wood, P. A. (2020). J. Appl. Cryst. 53, 226–235.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationNieger, M., Herold, D. & Vogtle, F. (2004). CSD Communication (refcode YAFNID) CCDC, Cambridge, England.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSpek, A. L. (2020). Acta Cryst. E76, 1–11.  Web of Science CrossRef IUCr Journals Google Scholar
First citationYang, M., Zhang, X., Wang, M. & Wang, M. (2016). Chin. J. Org. Chem. 36, 399–405.  Web of Science CSD CrossRef CAS Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

Journal logoIUCrDATA
ISSN: 2414-3146