Stereoselective rhodium-catalyzed 2-C‒H 1,3-dienylation of indoles: dual functions of the directing group
Zhai, Yizhan; Zhang, Xue; Ma, Shengming; Chemical Science  (2021) –; doi:10.1039/D1SC02167B

data_1564281
_publ_section_title
;
 Stereoselective rhodium-catalyzed 2-C--H 1,3-dienylation of indoles: dual
 functions of the directing group
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D1SC02167B
_journal_year                    2021
_chemical_formula_moiety         'C23 H18 Br N3 O'
_chemical_formula_sum            'C23 H18 Br N3 O'
_chemical_formula_weight         432.31
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-10-12
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-07-04 deposited with the CCDC.	2021-07-16 downloaded from the CCDC.
;
_cell_angle_alpha                95.198(4)
_cell_angle_beta                 91.243(4)
_cell_angle_gamma                108.491(4)
_cell_formula_units_Z            2
_cell_length_a                   7.4828(5)
_cell_length_b                   7.7696(6)
_cell_length_c                   16.9566(12)
_cell_measurement_reflns_used    6086
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      54.86
_cell_measurement_theta_min      4.56
_cell_volume                     929.76(12)
_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 (Sheldrick, 2015)'
_diffrn_ambient_temperature      170.0
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.0670
_diffrn_reflns_av_unetI/netI     0.0740
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            9015
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         54.991
_diffrn_reflns_theta_min         4.563
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.163
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.4688
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1691 before and 0.0925 after correction. The Ratio of minimum to maximum transmission is 0.6244. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.544
_exptl_crystal_description       block
_exptl_crystal_F_000             440
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.06
_refine_diff_density_max         2.110
_refine_diff_density_min         -2.097
_refine_diff_density_rms         0.201
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         3490
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0914
_refine_ls_R_factor_gt           0.0808
_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^)+(0.1960P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2228
_refine_ls_wR_factor_ref         0.2407
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2968
_reflns_number_total             3490
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1sc02167b2.cif
_cod_data_source_block           mj19656_0m
_cod_database_code               1564281
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.881
_shelx_estimated_absorpt_t_min   0.797
_olex2_refinement_description
;
1. 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
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C6(H6), C7(H7), C9(H9), C10(H10), C12(H12), C14(H14),
 C16(H16), C17(H17), C20(H20), C21(H21), C22(H22)
2.b X=CH2 refined with riding coordinates:
 C1(H1A,H1B)
2.c Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C)
;
_shelx_res_checksum              7474
_shelx_hkl_checksum              47589
_olex2_submission_special_instructions 'No special instructions were received'