(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_1553732
_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         'C11 H14 Cl2 F3 N O2 S2'
_chemical_formula_sum            'C11 H14 Cl2 F3 N O2 S2'
_chemical_formula_weight         384.25
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2016-07-21
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_audit_update_record
;
2017-01-15 deposited with the CCDC.
2017-02-10 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.0620(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.7869(6)
_cell_length_b                   10.8732(8)
_cell_length_c                   8.8809(7)
_cell_measurement_reflns_used    5654
_cell_measurement_temperature    130
_cell_measurement_theta_max      30.67
_cell_measurement_theta_min      2.63
_cell_volume                     749.00(10)
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      130
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_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  0.0147
_diffrn_reflns_av_unetI/netI     0.0251
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            7661
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.672
_diffrn_reflns_theta_min         2.302
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.746
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6619
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0582 before and 0.0304 after correction.
The Ratio of minimum to maximum transmission is 0.8871.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.704
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             392
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.428
_refine_diff_density_min         -0.616
_refine_diff_density_rms         0.060
_refine_ls_abs_structure_details
;
 Flack x determined using 1940 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.056(19)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         4461
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0292
_refine_ls_R_factor_gt           0.0285
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0371P)^2^+0.3150P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0720
_refine_ls_wR_factor_ref         0.0725
_reflns_Friedel_coverage         0.840
_reflns_Friedel_fraction_full    0.967
_reflns_Friedel_fraction_max     0.923
_reflns_number_gt                4364
_reflns_number_total             4461
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7qo00042a2.cif
_cod_data_source_block           mo_dm16474_0m
_cod_database_code               1553732
_shelx_estimated_absorpt_t_max   0.853
_shelx_estimated_absorpt_t_min   0.807
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2), C6(H6)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C7(H7A,H7B), C8(H8A,H8B)
2.c Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C10(H10A,H10B,H10C)
;
_shelx_res_checksum              16466
_shelx_hkl_checksum              91092
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'