(1S)-(−)-N-Trifluoromethylthio-2,10-camphorsultam and its derivatives: easily available, optically pure reagents for asymmetric trifluoromethylthiolation
Zhang, He; Leng, Xuebing; Wan, Xiaolong; Shen, Qilong; Organic Chemistry Frontiers 4 (2017) 1051–; doi:10.1039/C7QO00042A

data_1553729
_publ_section_title
;
 (1S)-(&#x2212;)-N-Trifluoromethylthio-2,10-camphorsultam and its
 derivatives: easily available, optically pure reagents for asymmetric
 trifluoromethylthiolation
;
_journal_issue                   6
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              1051
_journal_paper_doi               10.1039/C7QO00042A
_journal_volume                  4
_journal_year                    2017
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C19 H10 F4 O2 S'
_chemical_formula_sum            'C19 H10 F4 O2 S'
_chemical_formula_weight         378.33
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2016-10-19
_audit_creation_method
;
Olex2 1.2
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_audit_update_record
;
2017-01-15 deposited with the CCDC.
2017-02-10 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.6977(5)
_cell_length_b                   8.1914(6)
_cell_length_c                   30.513(2)
_cell_measurement_reflns_used    9943
_cell_measurement_temperature    130
_cell_measurement_theta_max      30.639
_cell_measurement_theta_min      2.57
_cell_volume                     1674.1(2)
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      130
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0202
_diffrn_reflns_av_unetI/netI     0.0206
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       41
_diffrn_reflns_limit_l_min       -43
_diffrn_reflns_number            17063
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         30.677
_diffrn_reflns_theta_min         2.575
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.246
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6139
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0524 before and 0.0394 after correction.
The Ratio of minimum to maximum transmission is 0.8228.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.501
_exptl_crystal_description       block
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.327
_refine_diff_density_min         -0.250
_refine_diff_density_rms         0.050
_refine_ls_abs_structure_details
;
 Flack x determined using 1989 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.004(19)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         5168
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0353
_refine_ls_R_factor_gt           0.0334
_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^)+(0.0483P)^2^+0.3678P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0865
_refine_ls_wR_factor_ref         0.0875
_reflns_Friedel_coverage         0.734
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.992
_reflns_number_gt                4931
_reflns_number_total             5168
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7qo00042a2.cif
_cod_data_source_block           mo_dm16671_0m
_cod_original_cell_volume        1674.0(2)
_cod_database_code               1553729
_shelx_estimated_absorpt_t_max   0.953
_shelx_estimated_absorpt_t_min   0.941
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C7(H7), C8(H8), C11(H11), C13(H13), C14(H14), C16(H16),
 C18(H18), C19(H19)
;
_shelx_res_checksum              25270
_shelx_hkl_checksum              23887
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'