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_7152972
_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_absolute_configuration rmad
_chemical_compound_source        dimethylsulfoxid
_chemical_formula_moiety         'C19 H16 Cl N3 , C2 H6 O S'
_chemical_formula_sum            'C21 H22 Cl N3 O S'
_chemical_formula_weight         399.93
_space_group_IT_number           2
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_block_code                GUL-GC-528-01
_audit_creation_date             2011-12-19
_audit_creation_method           SHELXL-97
_cell_angle_alpha                83.171(2)
_cell_angle_beta                 75.762(2)
_cell_angle_gamma                89.106(2)
_cell_formula_units_Z            4
_cell_length_a                   10.3396(3)
_cell_length_b                   11.1324(3)
_cell_length_c                   18.1230(5)
_cell_measurement_reflns_used    6505
_cell_measurement_temperature    100
_cell_measurement_theta_max      63.8067
_cell_measurement_theta_min      3.9997
_cell_volume                     2007.42(10)
_computing_cell_refinement       'SAINT software (Bruker AXS, 2004)'
_computing_data_collection       'PROTEUM2 (Bruker AXS, 2008)'
_computing_data_reduction        'SAINT software (Bruker AXS, 2004)'
_computing_molecular_graphics    'DIAMOND (Crystal Impact GbR, 2005)'
_computing_structure_refinement  'SHELXL-97 (G. M. Sheldrick, 2008)'
_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 0.965
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measurement_device_type  'Bruker AXS X8 Proteum'
_diffrn_measurement_method       'CCD \f- and \w-scans'
_diffrn_radiation_monochromator  'focusing multilayer optic'
_diffrn_radiation_source         '0.2 x 2mm^2^ focus rotating anode'
_diffrn_radiation_type           Cu-K\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0823
_diffrn_reflns_av_sigmaI/netI    0.0554
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            41515
_diffrn_reflns_theta_full        64.60
_diffrn_reflns_theta_max         64.60
_diffrn_reflns_theta_min         2.53
_exptl_absorpt_coefficient_mu    2.777
_exptl_absorpt_correction_T_max  0.87281
_exptl_absorpt_correction_T_min  0.60398
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   'SADABS (Bruker AXS, 2008)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.323
_exptl_crystal_description       plate
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.238
_refine_diff_density_min         -0.368
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     491
_refine_ls_number_reflns         6514
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0622
_refine_ls_R_factor_gt           0.0414
_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^)+(0.0343P)^2^+1.6515P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0946
_refine_ls_wR_factor_ref         0.1051
_reflns_number_gt                5028
_reflns_number_total             6514
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3ob40919h.txt
_cod_data_source_block           7642sadabs
_cod_original_sg_symbol_Hall     '-p 1'
_cod_original_sg_symbol_H-M      'p -1'
_cod_database_code               7152972