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_1569429
_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_absolute_configuration ad
_chemical_formula_moiety         'C34 H33 N O3 S'
_chemical_formula_sum            'C34 H33 N O3 S'
_chemical_formula_weight         535.67
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2022-11-18
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2023-02-19 deposited with the CCDC.	2023-07-03 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.1729(4)
_cell_length_b                   15.6495(7)
_cell_length_c                   19.8440(8)
_cell_measurement_reflns_used    9891
_cell_measurement_temperature    200.00
_cell_measurement_theta_max      68.204
_cell_measurement_theta_min      3.597
_cell_volume                     2848.6(2)
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      200.00
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0538
_diffrn_reflns_av_unetI/netI     0.0255
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            44830
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.202
_diffrn_reflns_theta_min         3.597
_diffrn_source_current           50.0
_diffrn_source_power             2.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.282
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.6768
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0945 before and 0.0776 after correction.
The Ratio of minimum to maximum transmission is 0.8987.
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    1.249
_exptl_crystal_description       block
_exptl_crystal_F_000             1136
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.527
_refine_diff_density_min         -0.183
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details
;
 Flack x determined using 2104 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.038(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     358
_refine_ls_number_reflns         5193
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0436
_refine_ls_R_factor_gt           0.0424
_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^)+(0.0787P)^2^+0.7543P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1180
_refine_ls_wR_factor_ref         0.1191
_reflns_Friedel_coverage         0.763
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                5013
_reflns_number_total             5193
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3sc02714g2.cif
_cod_data_source_block           s_CCDC1
_cod_depositor_comments
'Adding full bibliography for 1569428--1569430.cif.'
_cod_database_code               1569429
_shelx_shelxl_version_number     2019/2
_shelx_estimated_absorpt_t_max   0.882
_shelx_estimated_absorpt_t_min   0.628
_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, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C10(H10), C18(H18), C20(H20), C26(H26), C28(H28), C30(H30), C32(H32),
 C34(H34), C17(H17), C9(H9), C21(H21), C11(H11), C23(H23), C3(H3), C25(H25),
 C13(H13), C27(H27)
2.b Idealised Me refined as rotating group:
 C29(H29A,H29B,H29C), C15(H15A,H15B,H15C), C31(H31A,H31B,H31C), C2(H2A,H2B,
 H2C), C33(H33A,H33B,H33C)
2.c Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_shelx_res_checksum              68012
_olex2_submission_special_instructions 'No special instructions were received'