The first spontaneous resolution of a sulfoxide: Dianin's compound analogue, (<i>R</i>)-4-(4-hydroxyphenyl)-2,2,4-trimethylthiachroman-1-oxide
Gall, James H.; White, J. Derek; MacNicol, David D.; Frampton, Christopher S.; Acta Crystallographica Section E 74 (2018) 1633–1636; doi:10.1107/S2056989018014366

data_2242685
_publ_section_title
;
 The first spontaneous resolution of a sulfoxide: Dianin's compound
 analogue,
 (<i>R</i>)-4-(4-hydroxyphenyl)-2,2,4-trimethylthiachroman-1-oxide
;
_journal_coeditor_code           KQ2023
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              1633
_journal_page_last               1636
_journal_paper_doi               10.1107/S2056989018014366
_journal_volume                  74
_journal_year                    2018
_chemical_absolute_configuration ad
_chemical_formula_iupac          'C18 H20 O2 S'
_chemical_formula_moiety         'C18 H20 O2 S'
_chemical_formula_sum            'C18 H20 O2 S'
_chemical_formula_weight         300.40
_chemical_name_common
;
(<i>R</i>)-4-(4-Hydroxyphenyl)-2,2,4-trimethylthiachroman-1-oxide,
ThiaDianin's sulfoxide
;
_chemical_name_systematic
(<i>R</i>)-4-(4-Hydroxyphenyl)-2,2,4-trimethyl-3<i>H</i>-1\l^4^-benzothiopyran-1-one
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     difmap
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/6
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.4311(3)
_cell_length_b                   11.0892(3)
_cell_length_c                   12.8868(3)
_cell_measurement_reflns_used    3948
_cell_measurement_temperature    100.0(10)
_cell_measurement_theta_max      74.1550
_cell_measurement_theta_min      5.2510
_cell_volume                     1490.65(7)
_computing_cell_refinement
;
CrysAlisPro  (Rigaku OD, 2015)
;
_computing_data_collection
;
CrysAlisPro  (Rigaku OD, 2015)
;
_computing_data_reduction
;
CrysAlisPro  (Rigaku OD, 2015)
;
_computing_molecular_graphics
;
SHELXTL (Sheldrick, 2008), <i>Mercury</i> (Macrae <i>et al</i>.,
2008)
;
_computing_publication_material
;
SHELXTL (Sheldrick, 2008), <i>Mercury</i> (Macrae <i>et al</i>.,
2008) and
<i>publCIF</i> (Westrip, 2010)
;
_computing_structure_refinement
;
<i>SHELXL2014/6</i> (Sheldrick, 2015)
;
_computing_structure_solution
;
<i>SHELXD2014/6</i> (Schneider & Sheldrick, 2002)
;
_diffrn_ambient_temperature      100.0(10)
_diffrn_detector_area_resol_mean 5.2921
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type
'Rigaku Oxford Diffraction SuperNova, Dualflex, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0162
_diffrn_reflns_av_unetI/netI     0.0264
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            5735
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.498
_diffrn_reflns_theta_min         5.262
_diffrn_source                   'fine-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    1.935
_exptl_absorpt_correction_T_max  0.844
_exptl_absorpt_correction_T_min  0.786
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
(CrysAlisPro; Rigaku OD, 2015)
;
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.339
_exptl_crystal_description       Block
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.179
_exptl_crystal_size_mid          0.116
_exptl_crystal_size_min          0.103
_refine_diff_density_max         0.274
_refine_diff_density_min         -0.290
_refine_ls_abs_structure_details
;
Flack x determined using 1246 quotients
[(<i>I</i>^+^)-(<i>I</i>^-^)]/[(<i>I</i>^+^)+(<i>I</i>^-^)]
(Parsons <i>et al.</i>,  2013)
;
_refine_ls_abs_structure_Flack   -0.002(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     197
_refine_ls_number_reflns         3046
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0291
_refine_ls_R_factor_gt           0.0283
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0407P)^2^+0.4340P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0742
_refine_ls_wR_factor_ref         0.0750
_reflns_number_gt                2982
_reflns_number_total             3046
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            kq2023sup1.cif
_cod_data_source_block           I
_cod_database_code               2242685
_cod_database_fobs_code          2242685
_shelx_estimated_absorpt_t_min   0.723
_shelx_estimated_absorpt_t_max   0.826
_shelx_hkl_checksum              52506
_shelx_res_checksum              8796
_shelxl_version_number           2014/6