A Greener and Efficient Access to Substituted Four- and Six-membered Sulfur-bearing Heterocycles
Parisi, Giovanna; Degennaro, Leonardo; Carlucci, Claudia; de Candia, Modesto; Mastrorilli, Pietro; Roller, Alexander; Holzer, Wolfgang; Altomare, Cosimo Damiano; Pace, Vittorio; Luisi, Renzo; Org. Biomol. Chem.  (2017) –; doi:10.1039/C7OB00846E

data_7155649
_publ_section_title
;
 A Greener and Efficient Access to Substituted Four- and Six-membered
 Sulfur-bearing Heterocycles
;
_journal_name_full               'Org. Biomol. Chem.'
_journal_paper_doi               10.1039/C7OB00846E
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C19 H12 F6 O4 S'
_chemical_formula_sum            'C19 H12 F6 O4 S'
_chemical_formula_weight         450.35
_chemical_name_systematic
' (1,1-dioxido-2,4-thietanediyl)bis{[4-(trifluoromethyl)phenyl]}'
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_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
_audit_creation_date             2017-03-21
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.02 svn.r3394 for OlexSys, GUI svn.r5324)
;
_audit_update_record
;
2017-03-31 deposited with the CCDC.
2017-05-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.698(6)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.8749(15)
_cell_length_b                   6.3714(12)
_cell_length_c                   15.789(3)
_cell_measurement_reflns_used    9683
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      31.542
_cell_measurement_theta_min      2.531
_cell_volume                     888.4(3)
_computing_cell_refinement       'APEX2 v2013.6-2'
_computing_data_collection       'APEX2 v2013.6-2'
_computing_data_reduction        'APEX2 v2013.6-2'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.0
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0999
_diffrn_reflns_av_unetI/netI     0.0444
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            68662
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.736
_diffrn_reflns_theta_min         2.306
_diffrn_source                   'sealed  X-ray tube'
_diffrn_source_type              'Incoatec IuSMo'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.269
_exptl_absorpt_correction_T_max  0.7463
_exptl_absorpt_correction_T_min  0.4748
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction. 
wR2(int) was 0.1467 before and 0.1013 after correction. 
The Ratio of minimum to maximum transmission is 0.6362. 
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.684
_exptl_crystal_description       needle
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.636
_exptl_crystal_size_mid          0.087
_exptl_crystal_size_min          0.061
_refine_diff_density_max         0.725
_refine_diff_density_min         -0.465
_refine_diff_density_rms         0.077
_refine_ls_abs_structure_details
;
 Flack x determined using 2278 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.01(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         5989
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0548
_refine_ls_R_factor_gt           0.0461
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[\s^2^(Fo^2^)+(0.0741P)^2^+0.2431P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1158
_refine_ls_wR_factor_ref         0.1203
_reflns_Friedel_coverage         0.846
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.988
_reflns_number_gt                5350
_reflns_number_total             5989
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7ob00846e2.cif
_cod_data_source_block           mo_vipabag1_p21
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7155649
_shelxl_version_number           2013-3
_shelx_estimated_absorpt_t_max   0.984
_shelx_estimated_absorpt_t_min   0.847