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_7120146
_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         'C25 H14 F2 N2 O'
_chemical_formula_sum            'C25 H14 F2 N2 O'
_chemical_formula_weight         396.38
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -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                112.27(3)
_cell_angle_beta                 97.74(3)
_cell_angle_gamma                97.06(3)
_cell_formula_units_Z            8
_cell_length_a                   9.2966(19)
_cell_length_b                   19.662(4)
_cell_length_c                   23.710(5)
_cell_measurement_reflns_used    9511
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      27.8465
_cell_measurement_theta_min      1.7505
_cell_volume                     3902.0(18)
_computing_cell_refinement       crystalclear
_computing_data_collection       crystalclear
_computing_data_reduction        crystalclear
_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_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Rigaku Saturn 70 CCD'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0511
_diffrn_reflns_av_unetI/netI     0.0833
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            30163
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        25.019
_diffrn_reflns_theta_max         25.019
_diffrn_reflns_theta_min         1.750
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_T_max  0.9885
_exptl_absorpt_correction_T_min  0.9809
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   crystalclear
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.350
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1632
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.277
_refine_diff_density_min         -0.285
_refine_diff_density_rms         0.062
_refine_ls_extinction_coef       0.0152(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/8 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1098
_refine_ls_number_reflns         13575
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      15.905
_refine_ls_R_factor_all          0.1000
_refine_ls_R_factor_gt           0.0719
_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^)+(0.0652P)^2^+3.0020P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1622
_refine_ls_wR_factor_ref         0.1803
_reflns_Friedel_coverage         0.000
_reflns_number_gt                9840
_reflns_number_total             13575
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7cc02808c2.cif
_cod_data_source_block           r150714d1
_cod_original_cell_volume        3901.8(16)
_cod_database_code               7120146
_shelx_shelxl_version_number     2014/8
_shelx_estimated_absorpt_t_max   0.989
_shelx_estimated_absorpt_t_min   0.981
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All O(H) groups
2. Restrained distances
 N3-H3B = N5-H5A = N7-H7
 0.9 with sigma of 0.01
3.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C15(H15), C16(H16), C18(H18), C19(H19),
 C21(H21), C22(H22), C24(H24), C25(H25), C27(H27), C28(H28), C29(H29), C30(H30),
  C40(H40), C41(H41), C43(H43), C44(H44), C46(H46), C47(H47), C49(H49),
 C50(H50), C52(H52), C53(H53), C54(H54), C55(H55), C65(H65), C66(H66), C68(H68),
  C69(H69), C71(H71), C72(H72), C74(H74), C75(H75), C77(H77), C78(H78),
 C79(H79), C80(H80), C90(H90), C91(H91), C93(H93), C94(H94), C96(H96), C97(H97),
  C99(H99), C100(H100)
3.b Idealised tetrahedral OH refined as rotating group:
 O1(H1), O2(H2A), O3(H3B), O4(H4A)
;
_shelx_res_checksum              98566
_olex2_submission_special_instructions 'No special instructions were received'