Catalytic hydroaminations of alkynes: A facile protocol to vinyl- carbazole derivatives via a frustrated Lewis pair mechanism
Zhao, Yunbo; Jin, Lvnan; Guo, Jing; Stephan, Douglas W.; Chemical Communications  (2022) –; doi:10.1039/D1CC07171H

data_7129680
_publ_section_title
;
 Catalytic hydroaminations of alkynes: A facile protocol to vinyl-
 carbazole derivatives via a frustrated Lewis pair mechanism
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D1CC07171H
_journal_year                    2022
_chemical_formula_moiety         'C20 H14 Cl N'
_chemical_formula_sum            'C20 H14 Cl N'
_chemical_formula_weight         303.793
_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'
_symmetry_Int_Tables_number      14
_audit_creation_date             2021-12-02
_audit_creation_method
;
Olex2 1.5
(compiled 2021.11.18 svn.ra9532c28 for OlexSys, GUI svn.r6429)
;
_audit_update_record
;
2021-12-20 deposited with the CCDC.	2022-02-07 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 106.317(1)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   11.7513(3)
_cell_length_b                   13.5528(3)
_cell_length_c                   19.9224(5)
_cell_measurement_reflns_used    520
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      41.19
_cell_measurement_theta_min      4.00
_cell_volume                     3045.10(13)
_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  'olex2.refine 1.5 (Bourhis et al., 2015)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_diffrn_ambient_temperature      150.00
_diffrn_measured_fraction_theta_full 0.9998
_diffrn_measured_fraction_theta_max 0.9987
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5417800000000002
_diffrn_reflns_av_R_equivalents  0.0877
_diffrn_reflns_av_unetI/netI     0.0326
_diffrn_reflns_Laue_measured_fraction_full 0.9998
_diffrn_reflns_Laue_measured_fraction_max 0.9987
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            66916
_diffrn_reflns_point_group_measured_fraction_full 0.9998
_diffrn_reflns_point_group_measured_fraction_max 0.9987
_diffrn_reflns_theta_full        67.6786
_diffrn_reflns_theta_max         68.29
_diffrn_reflns_theta_min         3.95
_diffrn_source_current           1.2
_diffrn_source_power             0.06
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.160
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.6288
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1170 before and 0.0781 after correction.
The Ratio of minimum to maximum transmission is 0.8349.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.325
_exptl_crystal_description       block
_exptl_crystal_F_000             1270.220
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.3407
_refine_diff_density_min         -0.4016
_refine_diff_density_rms         0.0533
_refine_ls_d_res_high            0.8298
_refine_ls_d_res_low             11.1861
_refine_ls_goodness_of_fit_ref   1.0376
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    54
_refine_ls_number_parameters     397
_refine_ls_number_reflns         5575
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0376
_refine_ls_R_factor_all          0.0554
_refine_ls_R_factor_gt           0.0413
_refine_ls_shift/su_max          0.0001
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0465P)^2^+1.5277P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1005
_refine_ls_wR_factor_ref         0.1106
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              10
_reflns_limit_h_min              -14
_reflns_limit_k_max              16
_reflns_limit_k_min              0
_reflns_limit_l_max              24
_reflns_limit_l_min              -9
_reflns_number_gt                4426
_reflns_number_total             5575
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d1cc07171h2.cif
_cod_data_source_block           11
_cod_depositor_comments
;

2024-06-28
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C40 H28 Cl2 N2'
_cod_original_formula_weight         607.587
_cod_original_formula_moiety         '2(C20 H14 Cl N)'
_cod_original_formula_units_Z            4
_cod_original_sg_symbol_Hall     '-P 2ybc (x-z,y,z)'
_cod_database_code               7129680
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C00C(H00C), C00D(H00D), C00F(H00F), C00G(H00G), C00H(H00H), C00I(H00I),
 C00J(H00J), C00K(H00K), C00L(H00L), C00N(H00N), C00O(H00O), C00P(H00P),
 C00R(H00R), C00S(H00S), C00T(H00T), C00V(H00V), C00X(H00X), C010(H010),
 C011(H011), C012(H012), C014(H014), C015(H015), C016(H016), C018(H018)
2.b X=CH2 refined with riding coordinates:
 C00Z(H00a,H00b), C017(H01a,H01b)
;
_olex2_submission_special_instructions 'No special instructions were received'