Chemo- and regioselective [3~+~2]-cycloadditions of thiocarbonyl ylides: crystal structures of <i>trans</i>-8-benzoyl-1,1,3,3-tetramethyl-7-trifluoromethyl-5-thiaspiro[3.4]octan-2-one and <i>trans</i>-3-benzoyl-2,2-diphenyl-4-(trifluoromethyl)tetrahydrothiophene
Linden, Anthony; Mlostoń, Grzegorz; Grzelak, Paulina; Heimgartner, Heinz; Acta Crystallographica Section E 74 (2018) 1705–1709; doi:10.1107/S2056989018015335

data_2242710
_publ_section_title
;
 Chemo- and regioselective [3~+~2]-cycloadditions of thiocarbonyl ylides:
 crystal structures of
 <i>trans</i>-8-benzoyl-1,1,3,3-tetramethyl-7-trifluoromethyl-5-thiaspiro[3.4]octan-2-one
 and
 <i>trans</i>-3-benzoyl-2,2-diphenyl-4-(trifluoromethyl)tetrahydrothiophene
;
_journal_coeditor_code           VM2212
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              1705
_journal_page_last               1709
_journal_paper_doi               10.1107/S2056989018015335
_journal_volume                  74
_journal_year                    2018
_chemical_formula_iupac          'C19 H21 F3 O2 S'
_chemical_formula_moiety         'C19 H21 F3 O2 S'
_chemical_formula_sum            'C19 H21 F3 O2 S'
_chemical_formula_weight         370.42
_chemical_melting_point          387.3
_chemical_name_systematic
<i>trans</i>-8-Benzoyl-1,1,3,3-tetramethyl-7-trifluoromethyl-5-thiaspiro[3.4]octan-2-one
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 103.8526(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.48510(10)
_cell_length_b                   15.4106(2)
_cell_length_c                   11.45570(10)
_cell_measurement_reflns_used    41828
_cell_measurement_temperature    160(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      2.0
_cell_volume                     1797.19(3)
_computing_cell_refinement
;
DENZO-SMN (Otwinowski & Minor, 1997)
;
_computing_data_collection
;
COLLECT (Nonius, 2000)
;
_computing_data_reduction
;
DENZO-SMN and SCALEPACK (Otwinowski & Minor, 1997)
;
_computing_molecular_graphics
;
ORTEPII (Johnson, 1976)
;
_computing_publication_material
;
SHELXL2018 (Sheldrick, 2015) and PLATON (Spek, 2015)
;
_computing_structure_refinement
;
SHELXL2018 (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      160(2)
_diffrn_detector                 '65 mm CCD camera on \k goniostat'
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Nonius KappaCCD area-detector'
_diffrn_measurement_method       '\w scans with \k offsets'
_diffrn_radiation_monochromator  'horizontally mounted graphite crystal'
_diffrn_radiation_source         'Nonius FR590 sealed tube generator'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0528
_diffrn_reflns_av_unetI/netI     0.0280
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            40775
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.499
_diffrn_reflns_theta_min         2.258
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.219
_exptl_absorpt_correction_T_max  0.949
_exptl_absorpt_correction_T_min  0.895
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(Blessing, 1995)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.369
_exptl_crystal_description       prism
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.323
_refine_diff_density_min         -0.390
_refine_ls_extinction_coef       0.0172(19)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method
;
SHELXL2018 (Sheldrick, 2015)
;
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     231
_refine_ls_number_reflns         4119
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0598
_refine_ls_R_factor_gt           0.0428
_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^)+(0.0563P)^2^+0.7139P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1030
_refine_ls_wR_factor_ref         0.1141
_reflns_number_gt                3322
_reflns_number_total             4120
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            vm2212sup1.cif
_cod_data_source_block           1a
_cod_database_code               2242710
_cod_database_fobs_code          2242710
_shelx_hkl_checksum              56324
_shelx_res_checksum              11173