Copper-catalyzed tri- or tetrafunctionalization of alkenylboronic acids to prepare tetrahydrocarbazol-1-ones and indolo[2,3-a]carbazoles
Bi, Hong-Yan; Li, Cheng-Jing; Wei, Cui; Liang, Cui; Mo, Dong-Liang; Green Chemistry 22 (2020) 5815–5821; doi:10.1039/D0GC01514H

data_7241086
_publ_section_title
;
 Copper-catalyzed tri- or tetrafunctionalization of alkenylboronic acids
 to prepare tetrahydrocarbazol-1-ones and indolo[2,3-a]carbazoles
;
_journal_issue                   17
_journal_name_full               'Green Chemistry'
_journal_page_first              5815
_journal_page_last               5821
_journal_paper_doi               10.1039/D0GC01514H
_journal_volume                  22
_journal_year                    2020
_chemical_formula_moiety         'C13 H13 N O'
_chemical_formula_sum            'C13 H13 N O'
_chemical_formula_weight         199.24
_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     direct
_audit_creation_date             2018-05-28
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.18 svn.r3508 for OlexSys, GUI svn.r5497)
;
_audit_update_record
;
2020-05-03 deposited with the CCDC.	2020-08-20 downloaded from the CCDC.
;
_cell_angle_alpha                78.722(6)
_cell_angle_beta                 76.248(6)
_cell_angle_gamma                86.236(6)
_cell_formula_units_Z            2
_cell_length_a                   5.923(3)
_cell_length_b                   8.454(4)
_cell_length_c                   10.773(5)
_cell_measurement_reflns_used    4504
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      1.00000
_cell_measurement_theta_min      0.10312
_cell_volume                     513.8(4)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0291
_diffrn_reflns_av_unetI/netI     0.0276
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6136
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.461
_diffrn_reflns_theta_min         1.981
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.10000
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            white
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.288
_exptl_crystal_description       irregular
_exptl_crystal_F_000             212
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.18
_exptl_transmission_factor_max   1.00000
_exptl_transmission_factor_min   0.10000
_refine_diff_density_max         0.425
_refine_diff_density_min         -0.283
_refine_diff_density_rms         0.073
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     137
_refine_ls_number_reflns         2125
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.082
_refine_ls_R_factor_all          0.0549
_refine_ls_R_factor_gt           0.0507
_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^)+(0.0764P)^2^+0.1226P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1390
_refine_ls_wR_factor_ref         0.1435
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1903
_reflns_number_total             2125
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0gc01514h2.cif
_cod_data_source_block           aaaa
_cod_depositor_comments
;Adding full bibliography for 7241086.cif.

 Adding full bibliography for 7241086.cif.
;
_cod_database_code               7241086
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.985
_shelx_estimated_absorpt_t_min   0.976
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C12(H12)
2.b Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C6(H6A,H6B)
2.c Aromatic/amide H refined with riding coordinates:
 N2(H2), C7(H7), C10(H10), C13(H13), C14(H14)
2.d Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C)
;
_shelx_res_checksum              87000
_olex2_submission_special_instructions 'No special instructions were received'