Ru(ii)-catalyzed regioselective oxidative Heck reaction with internal olefins that tolerated strongly coordinating heterocycles.
Chen, Ci; Zhang, Qiaoya; Huang, Zhiwei; Ouyang, Wensen; Gao, Yang; Luo, Jiye; Liu, Yuan; Huo, Yanping; Chen, Qian; Li, Xianwei; Chemical science 15 (2024) 20064–20072; doi:10.1039/d4sc07036d

data_1573213
_publ_section_title
;
 Ru(ii)-catalyzed regioselective oxidative Heck reaction with internal
 olefins that tolerated strongly coordinating heterocycles.
;
_journal_issue                   47
_journal_name_full               'Chemical science'
_journal_page_first              20064
_journal_page_last               20072
_journal_paper_doi               10.1039/d4sc07036d
_journal_volume                  15
_journal_year                    2024
_chemical_absolute_configuration rm
_chemical_formula_moiety         'C10 H8 Br N O2 S'
_chemical_formula_sum            'C10 H8 Br N O2 S'
_chemical_formula_weight         286.14
_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'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2024-05-27
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2024-06-05 deposited with the CCDC.	2024-11-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   3.99710(10)
_cell_length_b                   7.0195(2)
_cell_length_c                   40.9871(10)
_cell_measurement_reflns_used    9171
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      27.14
_cell_measurement_theta_min      2.94
_cell_volume                     1150.00(5)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      297.97
_diffrn_measured_fraction_theta_full 0.945
_diffrn_measured_fraction_theta_max 0.936
_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  0.0440
_diffrn_reflns_av_unetI/netI     0.0562
_diffrn_reflns_Laue_measured_fraction_full 0.945
_diffrn_reflns_Laue_measured_fraction_max 0.936
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       45
_diffrn_reflns_limit_l_min       -52
_diffrn_reflns_number            7436
_diffrn_reflns_point_group_measured_fraction_full 0.950
_diffrn_reflns_point_group_measured_fraction_max 0.941
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.277
_diffrn_reflns_theta_min         2.944
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.734
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.5298
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0991 before and 0.0745 after correction.
The Ratio of minimum to maximum transmission is 0.7107.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.653
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.270
_refine_diff_density_min         -0.370
_refine_diff_density_rms         0.050
_refine_ls_abs_structure_details
;
 Flack x determined using 791 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.044(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     138
_refine_ls_number_reflns         2426
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0360
_refine_ls_R_factor_gt           0.0317
_refine_ls_shift/su_max          0.060
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0286P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0786
_refine_ls_wR_factor_ref         0.0805
_reflns_Friedel_coverage         0.636
_reflns_Friedel_fraction_full    0.958
_reflns_Friedel_fraction_max     0.950
_reflns_number_gt                2194
_reflns_number_total             2426
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc07036d2.cif
_cod_data_source_block           mo_20240527_lixw_0ma_a
_cod_depositor_comments          'Adding full bibliography for 1573213.cif.'
_cod_database_code               1573213
_shelx_shelxl_version_number     2018/3
_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:
 C2(H2), C8(H8)
2.b Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C10(H10A,H10B,H10C)
;
_shelx_res_checksum              49364
_shelx_hkl_checksum              88587
_olex2_submission_special_instructions 'No special instructions were received'