Cu(II)/Proline-Catalyzed Reductive Coupling of Sulfuryl Chloride and P(O)-H for P-S-C Bond Formation.
Zhang, Xinghua; Wang, Dungai; An, Duo; Han, Boshi; Song, Xiang; Li, Liang; Zhang, Gaoqi; Wang, Lixian; The Journal of organic chemistry 83 (2018) 1532–1537; doi:10.1021/acs.joc.7b02608

data_4033390
_publ_section_title
;
 Cu(II)/Proline-Catalyzed Reductive Coupling of Sulfuryl Chloride and
 P(O)-H for P-S-C Bond Formation.
;
_journal_issue                   3
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              1532
_journal_page_last               1537
_journal_paper_doi               10.1021/acs.joc.7b02608
_journal_volume                  83
_journal_year                    2018
_chemical_absolute_configuration rmad
_chemical_formula_sum            'C22 H15 O2 P S'
_chemical_formula_weight         374.37
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.4640(7)
_cell_length_b                   13.667(2)
_cell_length_c                   20.093(3)
_cell_measurement_reflns_used    1014
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      20.1520
_cell_measurement_theta_min      3.3860
_cell_volume                     1775.1(4)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0851
_diffrn_reflns_av_sigmaI/netI    0.1355
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            7393
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.98
_exptl_absorpt_coefficient_mu    0.286
_exptl_absorpt_correction_T_max  0.9557
_exptl_absorpt_correction_T_min  0.9345
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.401
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.200
_refine_diff_density_min         -0.190
_refine_diff_density_rms         0.049
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.8(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.854
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         3114
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.855
_refine_ls_R_factor_all          0.1255
_refine_ls_R_factor_gt           0.0678
_refine_ls_shift/su_max          0.010
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1486
_refine_ls_wR_factor_ref         0.1886
_reflns_number_gt                1846
_reflns_number_total             3114
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo7b02608_si_002.cif
_cod_data_source_block           a
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 

 Adding full bibliography for 4033390.cif.
;
_cod_original_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_database_code               4033390