Asymmetric rhodium-catalyzed click cycloaddition to access C-N axially chiral <i>N</i>-triazolyl indoles.
Zhou, Li; Li, Yankun; Li, Shunian; Shi, Zhenwei; Zhang, Xue; Tung, Chen-Ho; Xu, Zhenghu; Chemical science 14 (2023) 5182–5187; doi:10.1039/d3sc00610g

data_1568913
_publ_section_title
;
 Asymmetric rhodium-catalyzed click cycloaddition to access C-N axially
 chiral <i>N</i>-triazolyl indoles.
;
_journal_issue                   19
_journal_name_full               'Chemical science'
_journal_page_first              5182
_journal_page_last               5187
_journal_paper_doi               10.1039/d3sc00610g
_journal_volume                  14
_journal_year                    2023
_chemical_formula_moiety         'C31 H26 N4 O3 S'
_chemical_formula_sum            'C31 H26 N4 O3 S'
_chemical_formula_weight         534.62
_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             2022-07-25
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2022-07-25 deposited with the CCDC.	2023-04-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.2557(5)
_cell_length_b                   14.5568(9)
_cell_length_c                   21.8087(12)
_cell_measurement_reflns_used    5787
_cell_measurement_temperature    173.0
_cell_measurement_theta_max      68.519
_cell_measurement_theta_min      3.651
_cell_volume                     2620.9(3)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      173.0
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker D8 VENTURE PHOTON III'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0404
_diffrn_reflns_av_unetI/netI     0.0476
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            12512
_diffrn_reflns_point_group_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.513
_diffrn_reflns_theta_min         3.651
_diffrn_source_current           1.1
_diffrn_source_power             0.055
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    1.431
_exptl_absorpt_correction_T_max  0.7530
_exptl_absorpt_correction_T_min  0.6091
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0911 before and 0.0637 after correction.
The Ratio of minimum to maximum transmission is 0.8089.
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    1.355
_exptl_crystal_description       cube
_exptl_crystal_F_000             1120
_exptl_crystal_size_max          0.03
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.331
_refine_diff_density_min         -0.276
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details
;
 Flack x determined using 1684 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.020(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.104
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     354
_refine_ls_number_reflns         4693
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.104
_refine_ls_R_factor_all          0.0400
_refine_ls_R_factor_gt           0.0350
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0382P)^2^+0.1959P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0842
_refine_ls_wR_factor_ref         0.0878
_reflns_Friedel_coverage         0.727
_reflns_Friedel_fraction_full    0.962
_reflns_Friedel_fraction_max     0.954
_reflns_number_gt                4270
_reflns_number_total             4693
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3sc00610g2.cif
_cod_data_source_block           cu_220715c_0m
_cod_depositor_comments
'Adding full bibliography for 1568912--1568913.cif.'
_cod_database_code               1568913
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.972
_shelx_estimated_absorpt_t_min   0.958
_olex2_refinement_description
;
1.a Secondary CH2 refined with riding coordinates:
 C21(H21A,H21B)
1.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C9(H9), C10(H10), C12(H12), C14(H14), C16(H16), C17(H17), C18(H18),
 C19(H19), C20(H20), C22(H22), C23(H23), C25(H25), C26(H26), C27(H27), C28(H28),
  C29(H29), C30(H30)
1.c Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C), C31(H31A,H31B,H31C)
;
_shelx_res_checksum              55705
_shelx_hkl_checksum              72280
_olex2_submission_special_instructions 'No special instructions were received'