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_1568912
_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         'C29 H24 Fe N4 O2'
_chemical_formula_sum            'C29 H24 Fe N4 O2'
_chemical_formula_weight         516.37
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2022-07-21
_audit_creation_method
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_audit_update_record
;
2022-07-21 deposited with the CCDC.	2023-04-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 109.660(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.5500(9)
_cell_length_b                   10.0510(8)
_cell_length_c                   12.1412(10)
_cell_measurement_reflns_used    8034
_cell_measurement_temperature    173.0
_cell_measurement_theta_max      66.578
_cell_measurement_theta_min      3.866
_cell_volume                     1212.38(18)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_diffrn_ambient_temperature      173.0
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker D8 VENTURE PHOTON III'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0443
_diffrn_reflns_av_unetI/netI     0.0588
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            10500
_diffrn_reflns_point_group_measured_fraction_full 0.825
_diffrn_reflns_point_group_measured_fraction_max 0.825
_diffrn_reflns_theta_full        66.642
_diffrn_reflns_theta_max         66.642
_diffrn_reflns_theta_min         3.866
_exptl_absorpt_coefficient_mu    5.266
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.4256
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1379 before and 0.0855 after correction.
The Ratio of minimum to maximum transmission is 0.5654.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear light orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.414
_exptl_crystal_description       block
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.176
_refine_diff_density_min         -0.341
_refine_diff_density_rms         0.052
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.026(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     327
_refine_ls_number_reflns         3544
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.011
_refine_ls_R_factor_all          0.0399
_refine_ls_R_factor_gt           0.0299
_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^)+(0.0374P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0688
_refine_ls_wR_factor_ref         0.0706
_reflns_Friedel_coverage         0.565
_reflns_Friedel_fraction_full    0.636
_reflns_Friedel_fraction_max     0.636
_reflns_number_gt                3255
_reflns_number_total             3544
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3sc00610g2.cif
_cod_data_source_block           cu_220621e_0m
_cod_depositor_comments
'Adding full bibliography for 1568912--1568913.cif.'
_cod_database_code               1568912
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.858
_shelx_estimated_absorpt_t_min   0.779
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.974(6)
 0.026(6)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3.a Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B)
3.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C7(H7), C9(H9), C10(H10), C11(H11), C12(H12), C14(H14), C16(H16),
 C18(H18), C19(H19), C20(H20), C21(H21), C22(H22), C23(H23), C24(H24), C25(H25),
  C26(H26), C28(H28), C29(H29)
3.c Idealised Me refined as rotating group:
 C27(H27A,H27B,H27C)
;
_shelx_res_checksum              36385
_shelx_hkl_checksum              20252
_olex2_submission_special_instructions 'No special instructions were received'