Synthesis of 3-Aminotetrahydro-1H-carbazols by Visible-Light Photocatalyzed Cycloaddition of Cyclopropylanilines with 2-Alkenylarylisocyanides
Zhang, Xiaofei; Wang, Yao; Liu, Jiaxin; Tian, Chengpeng; Li, Xiang; Xie, Pan; Zhu, Zhen-Yu; Yao, Tuanli; Chemical Communications  (2023) –; doi:10.1039/D3CC04674E

data_7132334
_publ_section_title
;
 Synthesis of 3-Aminotetrahydro-1H-carbazols by Visible-Light
 Photocatalyzed Cycloaddition of Cyclopropylanilines with
 2-Alkenylarylisocyanides
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D3CC04674E
_journal_year                    2023
_chemical_formula_sum            'C24 H22 N2'
_chemical_formula_weight         338.43
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2023-05-26 deposited with the CCDC.	2023-11-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.556(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.4607(7)
_cell_length_b                   10.9217(8)
_cell_length_c                   17.9906(14)
_cell_measurement_reflns_used    4011
_cell_measurement_temperature    276(2)
_cell_measurement_theta_max      27.45
_cell_measurement_theta_min      2.86
_cell_volume                     1846.8(2)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      276(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.5287
_diffrn_reflns_av_unetI/netI     0.1492
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            52227
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.100
_diffrn_reflns_theta_max         25.100
_diffrn_reflns_theta_min         2.185
_exptl_absorpt_coefficient_mu    0.071
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.217
_exptl_crystal_description       block
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.233
_refine_diff_density_min         -0.242
_refine_diff_density_rms         0.103
_refine_ls_extinction_coef       0.0202(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   0.828
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         3280
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.828
_refine_ls_R_factor_all          0.1220
_refine_ls_R_factor_gt           0.0419
_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^)] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0816
_refine_ls_wR_factor_ref         0.0978
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1488
_reflns_number_total             3280
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc04674e2.cif
_cod_data_source_block           SUST_3497_0m
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7132334
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.992
_shelx_estimated_absorpt_t_max   0.993
_shelx_res_checksum              62748
_shelx_hkl_checksum              49597