Rhodium(III)-catalyzed intramolecular amidoarylation and hydroarylation of alkyne via C-H activation: switchable synthesis of 3,4-fused tricyclic indoles and chromans
Xue Zhang; Yifei Li; Hui Shi; Lunan Zhang; Shanshan Zhang; Xianxiu Xu; Qun Liu; Chem.Commun. 50 (2014) 7306–; doi:10.1039/C4CC02398F

data_7114625
_publ_section_title
;
 Rhodium(III)-catalyzed intramolecular amidoarylation and hydroarylation
 of alkyne via C-H activation: switchable synthesis of 3,4-fused tricyclic
 indoles and chromans
;
_journal_name_full               Chem.Commun.
_journal_page_first              7306
_journal_paper_doi               10.1039/C4CC02398F
_journal_volume                  50
_journal_year                    2014
_chemical_formula_sum            'C13 H15 N O2'
_chemical_formula_weight         217.26
_space_group_IT_number           161
_symmetry_cell_setting           rhombohedral
_symmetry_space_group_name_Hall  'R 3 -2"c'
_symmetry_space_group_name_H-M   'R 3 c :H'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_formula_units_Z            18
_cell_length_a                   25.053(2)
_cell_length_b                   25.053(2)
_cell_length_c                   9.6450(13)
_cell_measurement_temperature    293(2)
_cell_volume                     5242.7(9)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0592
_diffrn_reflns_av_sigmaI/netI    0.0456
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            9716
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.03
_diffrn_reflns_theta_min         1.63
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  0.9900
_exptl_absorpt_correction_T_min  0.9786
_exptl_crystal_density_diffrn    1.239
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2088
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.307
_refine_diff_density_min         -0.338
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0(3)
_refine_ls_extinction_coef       0.0016(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     151
_refine_ls_number_reflns         2054
_refine_ls_number_restraints     7
_refine_ls_restrained_S_all      1.086
_refine_ls_R_factor_all          0.0843
_refine_ls_R_factor_gt           0.0552
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0782P)^2^+5.0595P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1344
_refine_ls_wR_factor_ref         0.1525
_reflns_number_gt                1481
_reflns_number_total             2054
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4cc02398f2.cif
_cod_data_source_block           22
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_hydrogen_treatment' value 'MIXED' changed to 'mixed'
according to the built-in table from CIF Core dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 

2018-02-22
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_sg_symbol_H-M      R3C
_cod_original_formula_sum        'C39 H45 N3 O6'
_cod_original_formula_units_Z    6
_cod_original_formula_weight     651.78
_cod_database_code               7114625