Aerobic C-H amination of tetrahydrocarbazole derivatives via photochemically generated hydroperoxides.
Gulzar, Naeem; Klussmann, Martin; Organic & biomolecular chemistry 11 (2013) 4516–4520; doi:10.1039/c3ob40919h

data_7152973
_publ_section_title
;
 Aerobic C-H amination of tetrahydrocarbazole derivatives via
 photochemically generated hydroperoxides.
;
_journal_issue                   27
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              4516
_journal_page_last               4520
_journal_paper_doi               10.1039/c3ob40919h
_journal_volume                  11
_journal_year                    2013
_chemical_compound_source        dimethylsulfoxide
_chemical_formula_moiety         'C20 H21 N3, C2 H6 S O'
_chemical_formula_sum            'C22 H27 N3 O S'
_chemical_formula_weight         381.52
_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_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_block_code                GUL-GC-702-01
_audit_creation_date             2012-09-11
_cell_angle_alpha                90
_cell_angle_beta                 99.489(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   17.059(2)
_cell_length_b                   7.2199(9)
_cell_length_c                   17.196(2)
_cell_measurement_reflns_used    7194
_cell_measurement_temperature    100
_cell_measurement_theta_max      29.3858
_cell_measurement_theta_min      2.4017
_cell_volume                     2089.0(4)
_computing_cell_refinement       'SAINT software (Bruker AXS, 2004)'
_computing_data_collection       'APEX2 (Bruker AXS, 2008)'
_computing_data_reduction        'SAINT software (Bruker AXS, 2004)'
_computing_molecular_graphics    'DIAMOND (Crystal Impact GbR, 2005)'
_computing_structure_refinement  'SHELXL-2012-4 (Sheldrick, 2012)'
_computing_structure_solution    'SHELXS-97 (G. M. Sheldrick, 2008)'
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean 66.67
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker-AXS Kappa Mach3 APEX-II'
_diffrn_measurement_method       'CCD \f- and \w-scans'
_diffrn_radiation_monochromator  'Incoatec Helios mirrors'
_diffrn_radiation_source         '0.2 x 2mm^2^ focus rotating anode'
_diffrn_radiation_type           Mo-K\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0845
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            43886
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.744
_diffrn_reflns_theta_min         2.402
_exptl_absorpt_coefficient_mu    0.171
_exptl_absorpt_correction_T_max  0.99836
_exptl_absorpt_correction_T_min  0.98637
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   'SADABS (Bruker AXS, 2008)'
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.213
_exptl_crystal_description       needle
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.550
_refine_diff_density_min         -0.473
_refine_diff_density_rms         0.066
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     256
_refine_ls_number_reflns         6489
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.011
_refine_ls_R_factor_all          0.0851
_refine_ls_R_factor_gt           0.0491
_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^)+(0.0677P)^2^+0.7086P]
where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1164
_refine_ls_wR_factor_ref         0.1354
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4506
_reflns_number_total             6489
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c3ob40919h.txt
_cod_data_source_block           7982
_cod_original_sg_symbol_Hall     '-p 2yn'
_cod_original_sg_symbol_H-M      'p 21/n'
_cod_database_code               7152973
_shelx_estimated_absorpt_t_min   0.7662
_shelx_estimated_absorpt_t_max   1.0000
_diffrn_reflns_sigmai/neti       0.0544