When two symmetrically independent molecules must be different: “Crystallization-induced diastereomerization” of chiral pinanyl sulfone
Lodochnikova, Olga A.; Startseva, Valeriya A.; Nikitina, Liliya E.; Bodrov, Andrei V.; Klimovitskii, Alexander E.; Klimovitskii, Evgenii N.; Litvinov, Igor A.; CrystEngComm 16 (2014) 4314–; doi:10.1039/c3ce42642d

data_7215741
_publ_section_title
;
 When two symmetrically independent molecules must be different:
 &#x201C;Crystallization-induced diastereomerization&#x201D; of chiral
 pinanyl sulfone
;
_journal_issue                   20
_journal_name_full               CrystEngComm
_journal_page_first              4314
_journal_paper_doi               10.1039/c3ce42642d
_journal_volume                  16
_journal_year                    2014
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C12 H22 O3 S'
_chemical_formula_sum            'C12 H22 O3 S'
_chemical_formula_weight         246.36
_chemical_melting_point          342
_chemical_name_systematic
2-({((1S,2R,5S)-6,6-Dimethylbicyclo[3.1.1]hept-2-yl)methyl}sulfonyl)ethanol
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      4
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 100.430(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.982(3)
_cell_length_b                   6.4735(15)
_cell_length_c                   15.002(4)
_cell_measurement_temperature    296(2)
_cell_volume                     1335.4(6)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'PLATON for Windows (Farrugia, 1998)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    ' Direct_methods_(SIR,_Burla_et_al.,_1989)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.970
_diffrn_measured_fraction_theta_max 0.970
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0524
_diffrn_reflns_av_sigmaI/netI    0.0922
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            11312
_diffrn_reflns_theta_full        27.99
_diffrn_reflns_theta_max         27.99
_diffrn_reflns_theta_min         2.20
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.234
_exptl_absorpt_correction_T_max  0.9770
_exptl_absorpt_correction_T_min  0.9331
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.225
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plates
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.433
_refine_diff_density_min         -0.249
_refine_diff_density_rms         0.052
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.02(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.975
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     294
_refine_ls_number_reflns         5957
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      0.976
_refine_ls_R_factor_all          0.1310
_refine_ls_R_factor_gt           0.0601
_refine_ls_shift/su_max          0.047
_refine_ls_shift/su_mean         0.007
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0842P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1446
_refine_ls_wR_factor_ref         0.1743
_reflns_number_gt                3167
_reflns_number_total             5957
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3ce42642d2.cif
_cod_data_source_block           klim5
_cod_original_cell_volume        1335.4(5)
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7215741