A mechanistic investigation of the photoinduced, copper-mediated cross-coupling of an aryl thiol with an aryl halide.
Johnson, Miles W.; Hannoun, Kareem I.; Tan, Yichen; Fu, Gregory C.; Peters, Jonas C.; Chemical science 7 (2016) 4091–4100; doi:10.1039/C5SC04709A

data_1542546
_publ_section_title
;
 A mechanistic investigation of the photoinduced, copper-mediated
 cross-coupling of an aryl thiol with an aryl halide.
;
_journal_issue                   7
_journal_name_full               'Chemical science'
_journal_page_first              4091
_journal_page_last               4100
_journal_paper_doi               10.1039/C5SC04709A
_journal_volume                  7
_journal_year                    2016
_chemical_formula_moiety         'C16 H32 Na O8, C16 H18 Cu S2'
_chemical_formula_sum            'C32 H50 Cu Na O8 S2'
_chemical_formula_weight         713.37
_chemical_name_common            '[Cu(SAr)2][Na(12-crown-4)2]'
_chemical_name_systematic        '[Cu(SAr)2][Na(12-crown-4)2]'
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2015-06-17
_audit_creation_method
;
?
;
_audit_update_record
;
2015-12-07 deposited with the CCDC.
2016-02-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.682(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.5883(14)
_cell_length_b                   21.967(2)
_cell_length_c                   14.4286(16)
_cell_measurement_reflns_used    9920
_cell_measurement_temperature    100
_cell_measurement_theta_max      33.392
_cell_measurement_theta_min      2.678
_cell_volume                     3339.5(7)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.01
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1233
_diffrn_reflns_av_unetI/netI     0.1205
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       36
_diffrn_reflns_limit_k_min       -37
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            154949
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         37.007
_diffrn_reflns_theta_min         2.335
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.841
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9531
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/3 (Bruker,2014/3) was used for absorption correction.
wR2(int) was 0.0810 before and 0.0634 after correction.
The Ratio of minimum to maximum transmission is 0.9531.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.419
_exptl_crystal_description       block
_exptl_crystal_F_000             1512
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.640
_refine_diff_density_min         -0.547
_refine_diff_density_rms         0.111
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     401
_refine_ls_number_reflns         16419
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.1503
_refine_ls_R_factor_gt           0.0666
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0290P)^2^+3.2510P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0928
_refine_ls_wR_factor_ref         0.1104
_reflns_Friedel_coverage         0.000
_reflns_number_gt                9776
_reflns_number_total             16419
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5sc04709a2.cif
_cod_data_source_block           1
_cod_depositor_comments
;Adding full bibliography for 1542546.cif.

 Adding full bibliography for 1542546.cif.
;
_cod_original_cell_volume        3339.6(7)
_cod_database_code               1542546
_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 Secondary CH2 refined with riding coordinates:
 C25(H25A,H25B), C19(H19A,H19B), C00G(H00A,H00B), C24(H24A,H24B), C28(H28A,
 H28B), C22(H22A,H22B), C18(H18A,H18B), C27(H27A,H27B), C29(H29A,H29B),
 C23(H23A,H23B), C17(H17A,H17B), C31(H31A,H31B), C26(H26A,H26B), C30(H30A,H30B),
  C21(H21A,H21B), C20(H20A,H20B)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C3(H3), C12(H12), C11(H11), C13(H13), C5(H5)
2.c Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C7(H7A,H7B,H7C), C8(H8A,H8B,H8C), C15(H15A,H15B,H15C)
;
_shelx_res_checksum              89015
_shelx_shelxl_version_number     2014/7
_olex2_submission_original_sample_id '[Cu(SAr)2][Na(12-c-4)2] (1)'
_olex2_submission_special_instructions 'No special instructions were received'