Preparation of 3-Diazoindolin-2-imines via Cascade Reaction between Indoles and Sulfonylazides and Their Extensions to 2,3-Diaminoindoles and Imidazo[4,5-b]indoles.
Sheng, Guorong; Huang, Kai; Chi, Zhihao; Ding, Hualong; Xing, Yanpeng; Lu, Ping; Wang, Yanguang; Organic letters 16 (2014) 5096–5099; doi:10.1021/ol502423k

data_1517933
_publ_section_title
;
 Preparation of 3-Diazoindolin-2-imines via Cascade Reaction between
 Indoles and Sulfonylazides and Their Extensions to 2,3-Diaminoindoles and
 Imidazo[4,5-b]indoles.
;
_journal_issue                   19
_journal_name_full               'Organic letters'
_journal_page_first              5096
_journal_page_last               5099
_journal_paper_doi               10.1021/ol502423k
_journal_volume                  16
_journal_year                    2014
_chemical_formula_moiety         'C17 H16 N4 O2 S'
_chemical_formula_sum            'C17 H16 N4 O2 S'
_chemical_formula_weight         340.40
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_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                 95.860(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            16
_cell_length_a                   24.442(2)
_cell_length_b                   18.0516(14)
_cell_length_c                   14.9991(11)
_cell_measurement_reflns_used    6373
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.7175
_cell_measurement_theta_min      3.0483
_cell_volume                     6583.3(9)
_computing_cell_refinement       'CrysAlis PRO (Agilent Technologies, 2011)'
_computing_data_collection       'CrysAlis PRO'
_computing_data_reduction        'CrysAlis PRO'
_computing_molecular_graphics    'OLEX2 (Dolomanov et al., 2009)'
_computing_publication_material  OLEX2
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 10.3592
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0379
_diffrn_reflns_av_sigmaI/netI    0.0501
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            28732
_diffrn_reflns_theta_full        25.35
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_min         3.05
_exptl_absorpt_coefficient_mu    0.214
_exptl_absorpt_correction_T_max  0.9524
_exptl_absorpt_correction_T_min  0.9347
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlis PRO (Agilent Technologies, 2011) 
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.374
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             2848
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.23
_refine_diff_density_max         0.208
_refine_diff_density_min         -0.254
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       0.00018(6)
_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   1.012
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     878
_refine_ls_number_reflns         12023
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.012
_refine_ls_R_factor_all          0.1034
_refine_ls_R_factor_gt           0.0516
_refine_ls_shift/su_max          0.012
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0628P)^2^+1.1699P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1251
_refine_ls_wR_factor_ref         0.1554
_reflns_number_gt                6945
_reflns_number_total             12023
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol502423k_si_003.cif
_cod_data_source_block           140317_hr067
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1517933