Chiral carbon–sulfur center formation via Pd-catalyzed asymmetric allylic thioetherification: synthesis of allylic thioethers
Cai, Junmei; Cai, Juewang; Zheng, Purui; Wang, Xiaorong; Zhao, Xiaoming; RSC Adv. 7 (2017) 256–; doi:10.1039/C6RA26877C

data_7227327
_publ_section_title
;
 Chiral carbon--sulfur center formation via Pd-catalyzed asymmetric
 allylic thioetherification: synthesis of allylic thioethers
;
_journal_issue                   1
_journal_name_full               'RSC Adv.'
_journal_page_first              256
_journal_paper_doi               10.1039/C6RA26877C
_journal_volume                  7
_journal_year                    2017
_chemical_formula_sum            'C18 H16 Br2 S'
_chemical_formula_weight         424.19
_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'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_block_doi                 10.5517/ccdc.csd.cc1lvl56
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2016-06-14 deposited with the CCDC.
2016-12-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.604(8)
_cell_length_b                   9.541(10)
_cell_length_c                   24.58(3)
_cell_measurement_reflns_used    5794
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      23.43
_cell_measurement_theta_min      3.28
_cell_volume                     1783(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-III CMOS'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0662
_diffrn_reflns_av_unetI/netI     0.0711
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            21002
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.099
_diffrn_reflns_theta_min         2.804
_exptl_absorpt_coefficient_mu    4.654
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.580
_exptl_crystal_description       block
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.410
_exptl_crystal_size_mid          0.380
_exptl_crystal_size_min          0.100
_exptl_transmission_factor_max   0.7454
_exptl_transmission_factor_min   0.3804
_refine_diff_density_max         0.371
_refine_diff_density_min         -0.404
_refine_diff_density_rms         0.079
_refine_ls_abs_structure_details
; 
 Flack x determined using 638 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   -0.012(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         3893
_refine_ls_number_restraints     18
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.1302
_refine_ls_R_factor_gt           0.0528
_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^)+(0.0484P)^2^+0.8306P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0964
_refine_ls_wR_factor_ref         0.1194
_reflns_Friedel_coverage         0.718
_reflns_Friedel_fraction_full    0.993
_reflns_Friedel_fraction_max     0.980
_reflns_number_gt                2092
_reflns_number_total             3893
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6ra26877c2.cif
_cod_data_source_block           mo_160425b
_cod_database_code               7227327
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.251
_shelx_estimated_absorpt_t_max   0.653
_shelx_res_checksum              96562