TfOH-Catalyzed Reaction between 3-Diazoindolin-2-imines and Electron-Rich Arenes: Access to 3-Aryl-2-aminoindoles.
Qi, Jie; Wang, Zaibin; Lang, Bo; Lu, Ping; Wang, Yanguang; The Journal of organic chemistry 82 (2017) 12640–12646; doi:10.1021/acs.joc.7b02423

data_4033163
_publ_section_title
;
 TfOH-Catalyzed Reaction between 3-Diazoindolin-2-imines and Electron-Rich
 Arenes: Access to 3-Aryl-2-aminoindoles.
;
_journal_issue                   23
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              12640
_journal_page_last               12646
_journal_paper_doi               10.1021/acs.joc.7b02423
_journal_volume                  82
_journal_year                    2017
_chemical_formula_moiety         'C20 H17 Cl N2 O2 S2'
_chemical_formula_sum            'C20 H17 Cl N2 O2 S2'
_chemical_formula_weight         416.93
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_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_date             2016-12-15
_audit_creation_method
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_cell_angle_alpha                90.642(7)
_cell_angle_beta                 105.030(7)
_cell_angle_gamma                107.641(8)
_cell_formula_units_Z            2
_cell_length_a                   8.1156(7)
_cell_length_b                   11.1455(10)
_cell_length_c                   11.5815(9)
_cell_measurement_reflns_used    1996
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.4498
_cell_measurement_theta_min      3.0184
_cell_volume                     959.56(15)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293.15
_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_orient_matrix_UB_11      -0.0752006000
_diffrn_orient_matrix_UB_12      -0.0208105000
_diffrn_orient_matrix_UB_13      -0.0513799000
_diffrn_orient_matrix_UB_21      -0.0367173000
_diffrn_orient_matrix_UB_22      -0.0543348000
_diffrn_orient_matrix_UB_23      0.0277106000
_diffrn_orient_matrix_UB_31      -0.0458250000
_diffrn_orient_matrix_UB_32      0.0334243000
_diffrn_orient_matrix_UB_33      0.0255372000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0278
_diffrn_reflns_av_unetI/netI     0.0451
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5951
_diffrn_reflns_theta_full        25.35
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_min         3.02
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.435
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88054
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.443
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             432
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.46
_exptl_crystal_size_min          0.4
_refine_diff_density_max         0.465
_refine_diff_density_min         -0.348
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     250
_refine_ls_number_reflns         3489
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0666
_refine_ls_R_factor_gt           0.0503
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0658P)^2^+0.3034P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1240
_refine_ls_wR_factor_ref         0.1386
_reflns_number_gt                2721
_reflns_number_total             3489
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo7b02423_si_002.cif
_cod_data_source_block           161215_qj2_49_d
_cod_depositor_comments          'Adding full bibliography for 4033163.cif.'
_cod_original_cell_volume        959.55(14)
_cod_database_code               4033163
_chemical_oxdiff_formula         'c10 h10 n2 o8 S1 Cl1'
_reflns_odcompleteness_completeness 99.52
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 N2-H2
 0.86 with sigma of 0.02
3.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2A), C3(H3), C4(H4), C10(H10), C11(H11), C15(H15), C16(H16),
 C18(H18), C19(H19)
3.b Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C20(H20A,H20B,H20C)
;