Desulfurative Chlorination of Alkyl Phenyl Sulfides.
Canestrari, Daniele; Lancianesi, Stefano; Badiola, Eider; Strinna, Chiara; Ibrahim, Hasim; Adamo, Mauro F. A.; Organic letters 19 (2017) 918–921; doi:10.1021/acs.orglett.7b00077

data_1545199
_publ_section_title
;
 Desulfurative Chlorination of Alkyl Phenyl Sulfides.
;
_journal_issue                   4
_journal_name_full               'Organic letters'
_journal_page_first              918
_journal_page_last               921
_journal_paper_doi               10.1021/acs.orglett.7b00077
_journal_volume                  19
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C16 H16 Cl N O'
_chemical_formula_sum            'C16 H16 Cl N O'
_chemical_formula_weight         273.75
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 103.1880(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   28.4985(9)
_cell_length_b                   11.4777(4)
_cell_length_c                   9.0995(3)
_cell_measurement_reflns_used    9979
_cell_measurement_temperature    215(2)
_cell_measurement_theta_max      68.36
_cell_measurement_theta_min      3.19
_cell_volume                     2897.92(17)
_computing_cell_refinement       'SAINT+ Ver. 8.34A (Bruker, 2013)'
_computing_data_collection       'APEX2 Ver. 2014.11-0 (Bruker, 2014)'
_computing_data_reduction        'SAINT+ Ver. 8.34A (Bruker, 2013)'
_computing_molecular_graphics    'SHELXTL (Bruker, 2008-2014)'
_computing_publication_material  'SHELXTL (Bruker, 2008-2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT-2014/4 (Sheldrick, 2014)'
_diffrn_ambient_temperature      215(2)
_diffrn_detector_area_resol_mean 8.258
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0391
_diffrn_reflns_av_unetI/netI     0.0348
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            21152
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.525
_diffrn_reflns_theta_min         3.185
_diffrn_source                   'micro-focus sealed tube'
_exptl_absorpt_coefficient_mu    2.254
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.5432
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker, 2014/5) was used for absorption correction.
wR2(int) was 0.1174 before and 0.0707 after correction.
The Ratio of minimum to maximum transmission is 0.7213.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.255
_exptl_crystal_description       plate
_exptl_crystal_F_000             1152
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_min          0.080
_refine_diff_density_max         0.401
_refine_diff_density_min         -0.315
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details
; 
 Refined as an inversion twin. 
;
_refine_ls_abs_structure_Flack   0.06(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     321
_refine_ls_number_reflns         5295
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0438
_refine_ls_R_factor_gt           0.0423
_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^)+(0.0626P)^2^+1.7159P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1148
_refine_ls_wR_factor_ref         0.1166
_reflns_Friedel_coverage         0.898
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.997
_reflns_number_gt                5071
_reflns_number_total             5295
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol7b00077_si_002.cif
_cod_data_source_block           tcd354
_cod_depositor_comments          'Adding full bibliography for 1545199.cif.'
_cod_database_code               1545199
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.532
_shelx_estimated_absorpt_t_max   0.840
_shelx_res_checksum              13457
_shelx_hkl_checksum              12059