7,7-[Ethane-1,2-diylbis(oxy)]-2-[hydroxy(phenyl)methyl]bicyclo[3.3.1]nonan-3-one

In the title compound, C18H22O4, the cyclohexane and cyclohexanone rings adopt normal chair and half-chair conformations, respectively. The dioxolane ring is almost planar, with an r.m.s. deviation of 0.094 (3) Å. In the crystal, molecules are connected by O—H⋯O hydrogen bonds, forming 21 helical chains along the a-axis direction. The chains are further connected by C—H⋯O hydrogen bonds.

In the title compound, C 18 H 22 O 4 , the cyclohexane and cyclohexanone rings adopt normal chair and half-chair conformations, respectively. The dioxolane ring is almost planar, with an r.m.s. deviation of 0.094 (3) Å . In the crystal, molecules are connected by O-HÁ Á ÁO hydrogen bonds, forming 2 1 helical chains along the a-axis direction. The chains are further connected by C-HÁ Á ÁO hydrogen bonds.
supplementary materials . E70, o665 [doi:10.1107/S1600536814009040]  Recently. it was synthesized in our lab and the structure was determined.
In the compound (Fig. 1), the C1/C4 cyclohexyl ring adopts a normal chair conformation. The O1/O2 dioxolane ring is almost planar, with a maximum deviation 0.086 (4) Å at the O2 atom. Atoms C3, C7, C8, C9, C5 and O3 are arranged roughly on a plane, with the maximum deviation 0.171 (4) Å at C7 atom. Therefore, the C4/C8 cyclohexanone ring adopts a half-chair conformation, which is different from most known condensed cyclohexanone ring that is part of the complex structure (Lopez-Alvarado et al., 2002;Li et al., 2002), and from free cyclohexanone in solid state (Shallard-Brown et al., 2005).
In the crystal, molecules are linked by O4-H4···O3 i hydrogen bonds ( Fig. 2 and Table 1) to form chiral chains. In addition, C-H···O hydrogen bonds help the stability of the crystal. No π-π packing and C-H···π contacts are observed.

Refinement
The hydroxyl H atom was located in a difference Fourier map and was refined freely. Other H atoms were placed in calculated positions and allowed to ride on their parent atoms at distances 0.93 Å for phenyl, 0.97 Å for methylene and 0.98 Å for methine with U iso (H) = 1.2U eq (C). In the absence of significant anomalous scattering effects, Friedel pairs have been merged.  The molecular structure of the title compound with atom labels, showing 40% probability displacement ellipsoids.

Figure 2
The packing diagram of the title compound viewed down along the a axis. O-H···O hydrogen bonds are shown by thin dashed lines.  3488,2929,2901,2875,1685,1455,1332,1268,1215,1145,1094,1072,1044,1024,948 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 F 2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F 2 , conventional R-factors R are based on F, with F set to zero for negative F 2 . The threshold expression of F 2 > σ(F 2 ) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F 2 are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.