Rhodium-Catalyzed C2 and C4 C–H Activation/Annulation of 3-(1H-Indol-3-yl)-3-oxopropanenitriles with Internal Alkynes: A Facile Access to Substituted and Fused Carbazoles
Zhou, Tao; Li, Bin; Wang, Baiquan; Chem. Commun.  (2017) –; doi:10.1039/C7CC02808C

data_7120147
_publ_section_title
;
 Rhodium-Catalyzed C2 and C4 C--H Activation/Annulation of
 3-(1H-Indol-3-yl)-3-oxopropanenitriles with Internal Alkynes: A Facile
 Access to Substituted and Fused Carbazoles
;
_journal_name_full               'Chem. Commun.'
_journal_paper_doi               10.1039/C7CC02808C
_journal_year                    2017
_chemical_formula_moiety         'C39 H24 N2 O'
_chemical_formula_sum            'C39 H24 N2 O'
_chemical_formula_weight         536.60
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2017-03-07
_audit_creation_method
;
Olex2 1.2
(compiled 2017.02.23 svn.r3390 for OlexSys, GUI svn.r5320)
;
_audit_update_record
;
2017-03-11 deposited with the CCDC.
2017-05-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.622(4)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   18.329(3)
_cell_length_b                   21.067(3)
_cell_length_c                   16.730(3)
_cell_measurement_reflns_used    7416
_cell_measurement_temperature    113.15
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.0
_cell_volume                     6369.2(18)
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b42'
_computing_data_collection       'CrystalClear-SM Expert 2.1 b42 (Rigaku, 2015)'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b42'
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      113.15
_diffrn_detector_area_resol_mean 5.814
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Rigaku Xtalab P200'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0288
_diffrn_reflns_av_unetI/netI     0.0219
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            42665
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.697
_diffrn_reflns_theta_min         2.048
_exptl_absorpt_coefficient_mu    0.067
_exptl_absorpt_correction_T_max  0.9893
_exptl_absorpt_correction_T_min  0.9867
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.119
_exptl_crystal_density_method    "'not measured'"
_exptl_crystal_description       prism
_exptl_crystal_F_000             2240
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_platon_squeeze_details
;

;
_refine_diff_density_max         0.360
_refine_diff_density_min         -0.287
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     383
_refine_ls_number_reflns         8222
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0602
_refine_ls_R_factor_gt           0.0450
_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^)+(0.0802P)^2^+3.5208P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1097
_refine_ls_wR_factor_ref         0.1182
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6565
_reflns_number_total             8222
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7cc02808c2.cif
_cod_data_source_block           m20150512a
_cod_original_cell_volume        6369.3(17)
_cod_database_code               7120147
_shelx_shelxl_version_number     2014/8
_shelx_estimated_absorpt_t_max   0.989
_shelx_estimated_absorpt_t_min   0.987
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C17(H17), C18(H18), C19(H19), C20(H20), C21(H21),
 C23(H23), C24(H24), C25(H25), C26(H26), C27(H27), C29(H29), C30(H30), C31(H31),
  C32(H32), C33(H33), C35(H35), C36(H36), C37(H37), C38(H38), C39(H39)
;
_shelx_res_checksum              67955
_shelx_fab_checksum              69294
_olex2_submission_special_instructions 'No special instructions were received'