Rhodium-catalyzed atroposelective access to trisubstituted olefins <i>via</i> C-H bond olefination of diverse arenes.
Zhu, Xiaohan; Mi, Ruijie; Yin, Jie; Wang, Fen; Li, Xingwei; Chemical science 14 (2023) 7999–8005; doi:10.1039/d3sc02714g

data_1569428
_publ_section_title
;
 Rhodium-catalyzed atroposelective access to trisubstituted olefins
 <i>via</i> C-H bond olefination of diverse arenes.
;
_journal_issue                   29
_journal_name_full               'Chemical science'
_journal_page_first              7999
_journal_page_last               8005
_journal_paper_doi               10.1039/d3sc02714g
_journal_volume                  14
_journal_year                    2023
_chemical_formula_moiety         'C35 H31 N3 O4 S'
_chemical_formula_sum            'C35 H31 N3 O4 S'
_chemical_formula_weight         589.69
_space_group_crystal_system      hexagonal
_space_group_IT_number           170
_space_group_name_Hall           'P 65'
_space_group_name_H-M_alt        'P 65'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_block_doi                 10.5517/ccdc.csd.cc2fw0q2
_audit_creation_date             2023-05-03
_audit_creation_method
;
Olex2 1.5-alpha
(compiled 2022.06.10 svn.r3fa896fb for OlexSys, GUI svn.r6535)
;
_audit_update_record
;
2023-05-03 deposited with the CCDC.	2023-07-03 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            6
_cell_length_a                   21.8313(6)
_cell_length_b                   21.8313(6)
_cell_length_c                   11.5605(4)
_cell_measurement_reflns_used    9243
_cell_measurement_temperature    255.00
_cell_measurement_theta_max      68.356
_cell_measurement_theta_min      4.678
_cell_volume                     4771.6(2)
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      255.00
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0426
_diffrn_reflns_av_unetI/netI     0.0131
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            149628
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.492
_diffrn_reflns_theta_min         4.483
_diffrn_source_current           50.0
_diffrn_source_power             2.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.241
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.6421
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1066 before and 0.0743 after correction.
The Ratio of minimum to maximum transmission is 0.8526.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.231
_exptl_crystal_description       block
_exptl_crystal_F_000             1860
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.145
_refine_diff_density_min         -0.243
_refine_diff_density_rms         0.031
_refine_ls_abs_structure_details
;
 Flack x determined using 2601 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.036(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     396
_refine_ls_number_reflns         5768
_refine_ls_number_restraints     350
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0274
_refine_ls_R_factor_gt           0.0268
_refine_ls_shift/su_max          0.012
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0444P)^2^+0.5683P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0710
_refine_ls_wR_factor_ref         0.0715
_reflns_Friedel_coverage         0.874
_reflns_Friedel_fraction_full    0.976
_reflns_Friedel_fraction_max     0.969
_reflns_number_gt                5658
_reflns_number_total             5768
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3sc02714g2.cif
_cod_data_source_block           s
_cod_depositor_comments
'Adding full bibliography for 1569428--1569430.cif.'
_cod_original_cell_volume        4771.6(3)
_cod_database_code               1569428
_shelx_shelxl_version_number     2019/2
_shelx_estimated_absorpt_t_max   0.707
_shelx_estimated_absorpt_t_min   0.637
_olex2_refinement_description
;
1. Rigid bond restraints
 S1
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
2. Uiso/Uaniso restraints and constraints
S1: within 2A with sigma of 0.04 and sigma for terminal atoms of 0.08 within 2A
3. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C24(H24), C28(H28), C30(H30), C32(H32), C34(H34), C9(H9), C19(H19),
 C21(H21), C11(H11), C25(H25), C27(H27), C7(H7), C29(H29), C2(H2), C33(H33),
 C17(H17), C35(H35)
4.b Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C), C13(H13A,H13B,H13C), C15(H15A,H15B,H15C), C31(H31A,H31B,H31C)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              72972
_shelx_fab_checksum              2478
_olex2_submission_special_instructions 'No special instructions were received'