Palladium-catalyzed difluoromethylthiolation of heteroaryl bromides, iodides, triflates and aryl iodides
Wu, Jiang; Liu, Yafei; Lu, Changhui; Shen, Qilong; Chem. Sci. 7 (2016) 3757–; doi:10.1039/C6SC00082G

data_1542595
_publ_section_title
;
 Palladium-catalyzed difluoromethylthiolation of heteroaryl bromides,
 iodides, triflates and aryl iodides
;
_journal_issue                   6
_journal_name_full               'Chem. Sci.'
_journal_page_first              3757
_journal_paper_doi               10.1039/C6SC00082G
_journal_volume                  7
_journal_year                    2016
_chemical_formula_moiety         'C44 H36 Br N O P2 Pd'
_chemical_formula_sum            'C44 H36 Br N O P2 Pd'
_chemical_formula_weight         842.99
_chemical_name_systematic
;
 ?
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2015-10-16
_audit_creation_method
;
Olex2 1.2
(compiled 2014.07.22 svn.r2960 for OlexSys, GUI svn.r4862)
;
_audit_update_record
;
2015-11-13 deposited with the CCDC.
2016-02-26 downloaded from the CCDC.
;
_cell_angle_alpha                69.218(4)
_cell_angle_beta                 72.309(4)
_cell_angle_gamma                70.811(4)
_cell_formula_units_Z            2
_cell_length_a                   11.120(2)
_cell_length_b                   12.074(3)
_cell_length_c                   15.487(4)
_cell_measurement_reflns_used    2120
_cell_measurement_temperature    130
_cell_measurement_theta_max      23.55
_cell_measurement_theta_min      2.66
_cell_volume                     1794.3(7)
_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  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      130
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_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  0.0553
_diffrn_reflns_av_unetI/netI     0.0996
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            14978
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.714
_diffrn_reflns_theta_min         1.862
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.757
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.4851
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0854 before and 0.0487 after correction.
The Ratio of minimum to maximum transmission is 0.6506.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.560
_exptl_crystal_description       block
_exptl_crystal_F_000             852
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_refine_diff_density_max         1.368
_refine_diff_density_min         -1.253
_refine_diff_density_rms         0.138
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.972
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     453
_refine_ls_number_reflns         8389
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.972
_refine_ls_R_factor_all          0.0928
_refine_ls_R_factor_gt           0.0544
_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^)+(0.0637P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1207
_refine_ls_wR_factor_ref         0.1383
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5641
_reflns_number_total             8389
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6sc00082g2.cif
_cod_data_source_block           mo_dm15772_0m
_cod_depositor_comments          'Adding full bibliography for 1542595.cif.'
_cod_original_cell_volume        1794.2(7)
_cod_database_code               1542595
_shelxl_version_number           2014-3
_shelx_estimated_absorpt_t_max   0.872
_shelx_estimated_absorpt_t_min   0.779
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C9(H9), C10(H10), C11(H11), C17(H17), C18(H18),
 C19(H19), C20(H20), C21(H21), C23(H23), C24(H24), C25(H25), C26(H26), C27(H27),
  C29(H29), C30(H30), C31(H31), C32(H32), C33(H33), C35(H35), C36(H36),
 C37(H37), C38(H38), C39(H39), C41(H41), C42(H42), C43(H43), C44(H44)
2.b Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C15(H15A,H15B,H15C)
;
_shelx_res_checksum              46571
_olex2_submission_special_instructions 'No special instructions were received'