Rhodium-catalyzed C-H activation of 3-(indolin-1-yl)-3-oxopropanenitriles with diazo compounds and tandem cyclization leading to hydrogenated azepino[3,2,1-hi]indoles.
Zhou, Tao; Li, Bin; Wang, Baiquan; Chemical communications (Cambridge, England) 52 (2016) 14117–14120; doi:10.1039/c6cc07758g

data_7125235
_publ_section_title
;
 Rhodium-catalyzed C-H activation of 3-(indolin-1-yl)-3-oxopropanenitriles
 with diazo compounds and tandem cyclization leading to hydrogenated
 azepino[3,2,1-hi]indoles.
;
_journal_issue                   98
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              14117
_journal_page_last               14120
_journal_paper_doi               10.1039/c6cc07758g
_journal_volume                  52
_journal_year                    2016
_chemical_formula_moiety         'C17 H16 N2 O3'
_chemical_formula_sum            'C17 H16 N2 O3'
_chemical_formula_weight         296.32
_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
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2016-08-11 deposited with the CCDC.
2016-11-10 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.126(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.5064(9)
_cell_length_b                   17.8133(19)
_cell_length_c                   9.4824(10)
_cell_measurement_reflns_used    4505
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      27.50
_cell_measurement_theta_min      3.20
_cell_volume                     1418.7(3)
_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    'CrystalStructure 4.2'
_computing_publication_material  'CrystalStructure 4.2 (Rigaku, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT Version 2014/4 (Sheldrick, 2014)'
_diffrn_ambient_temperature      113(2)
_diffrn_detector_area_resol_mean 5.814
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       \w
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.1108
_diffrn_reflns_av_unetI/netI     0.0503
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            18579
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.737
_diffrn_reflns_theta_min         2.458
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_T_max  0.981
_exptl_absorpt_correction_T_min  0.926
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.387
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.430
_refine_diff_density_min         -0.240
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         3671
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0473
_refine_ls_R_factor_gt           0.0437
_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^)+(0.0565P)^2^+0.4807P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1179
_refine_ls_wR_factor_ref         0.1210
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3307
_reflns_number_total             3671
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6cc07758g2.cif
_cod_data_source_block           m20151113b
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7125235
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.977
_shelx_estimated_absorpt_t_max   0.981
_shelx_res_checksum              7246