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_1517931
_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         'C18 H16 N4 O2 S'
_chemical_formula_sum            'C18 H16 N4 O2 S'
_chemical_formula_weight         352.41
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_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_creation_method           SHELXL-97
_cell_angle_alpha                87.148(17)
_cell_angle_beta                 73.581(18)
_cell_angle_gamma                68.814(18)
_cell_formula_units_Z            2
_cell_length_a                   7.9850(15)
_cell_length_b                   9.3841(19)
_cell_length_c                   13.287(3)
_cell_measurement_reflns_used    1546
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.3013
_cell_measurement_theta_min      3.6270
_cell_volume                     888.9(3)
_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 0.996
_diffrn_measured_fraction_theta_max 0.996
_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  0.0230
_diffrn_reflns_av_sigmaI/netI    0.0411
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            5547
_diffrn_reflns_theta_full        25.35
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_min         3.63
_exptl_absorpt_coefficient_mu    0.201
_exptl_absorpt_correction_T_max  0.9609
_exptl_absorpt_correction_T_min  0.9098
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlis PRO (Agilent Technologies, 2011) 
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.317
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platelet
_exptl_crystal_F_000             368
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.302
_refine_diff_density_min         -0.326
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     231
_refine_ls_number_reflns         3241
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0851
_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^)+(0.0683P)^2^+0.2569P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1328
_refine_ls_wR_factor_ref         0.1607
_reflns_number_gt                2220
_reflns_number_total             3241
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol502423k_si_002.cif
_cod_data_source_block           140327_sgr2_076
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to
/home/saulius/struct/COD-crude-data--automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2827 2014-09-09 07:05:25Z andrius 
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_cod_database_code               1517931