Convenient Synthesis of 2-Amino-3-(arylthio)indoles via Rh-Catalyzed Reaction of 3-Diazoindol-2-imines with Thioesters
Ma, Fanghui; Qian, Jing; Lu, Ping; Wang, Yanguang; Organic & Biomolecular Chemistry  (2017) –; doi:10.1039/C7OB02597A

data_7156032
_publ_section_title
;
 Convenient Synthesis of 2-Amino-3-(arylthio)indoles via Rh-Catalyzed
 Reaction of 3-Diazoindol-2-imines with Thioesters
;
_journal_name_full               'Organic &amp; Biomolecular Chemistry'
_journal_paper_doi               10.1039/C7OB02597A
_journal_year                    2017
_chemical_formula_moiety         'C23 H17 Cl N2 O3 S2'
_chemical_formula_sum            'C23 H17 Cl N2 O3 S2'
_chemical_formula_weight         468.95
_space_group_crystal_system      trigonal
_space_group_IT_number           148
_space_group_name_Hall           '-R 3'
_space_group_name_H-M_alt        'R -3'
_symmetry_space_group_name_Hall  '-R 3'
_symmetry_space_group_name_H-M   'R -3 :H'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2017-04-11
_audit_creation_method
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Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_audit_update_record
;
2017-07-21 deposited with the CCDC.
2017-12-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            18
_cell_length_a                   31.8220(18)
_cell_length_b                   31.8220(18)
_cell_length_c                   13.3046(5)
_cell_measurement_reflns_used    7060
_cell_measurement_temperature    170.1
_cell_measurement_theta_max      29.3013
_cell_measurement_theta_min      3.3232
_cell_volume                     11667.8(10)
_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
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CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction
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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, 2015)'
_diffrn_ambient_temperature      170.1
_diffrn_detector_area_resol_mean 5.1796
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details
;
  1 omega  -39.00   53.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.6246   35.0000 -155.0000 92
;
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0221289000
_diffrn_orient_matrix_UB_12      -0.0207242000
_diffrn_orient_matrix_UB_13      0.0144058000
_diffrn_orient_matrix_UB_21      -0.0130756000
_diffrn_orient_matrix_UB_22      0.0108687000
_diffrn_orient_matrix_UB_23      -0.0193720000
_diffrn_orient_matrix_UB_31      -0.0013481000
_diffrn_orient_matrix_UB_32      -0.0107036000
_diffrn_orient_matrix_UB_33      -0.0475300000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0550
_diffrn_reflns_av_unetI/netI     0.0784
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       37
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       36
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            8077
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.348
_diffrn_reflns_theta_min         3.330
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.332
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80412
_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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.201
_exptl_crystal_description       block
_exptl_crystal_F_000             4356
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.302
_refine_diff_density_min         -0.523
_refine_diff_density_rms         0.058
_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     281
_refine_ls_number_reflns         4730
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0660
_refine_ls_R_factor_gt           0.0515
_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^)+(0.0557P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1215
_refine_ls_wR_factor_ref         0.1335
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3650
_reflns_number_total             4730
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7ob02597a2.cif
_cod_data_source_block           170411_mfh_451_173_3_sq
_cod_original_cell_volume        11667.7(14)
_cod_database_code               7156032
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         'c10 h10 n2 o8 S1 CL1'
_shelx_estimated_absorpt_t_max   0.907
_shelx_estimated_absorpt_t_min   0.857
_reflns_odcompleteness_completeness 99.53
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C10(H10), C11(H11), C12(H12), C13(H13),
 C19(H19), C20(H20), C22(H22), C23(H23)
2.c Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C)
;
_shelx_res_checksum              35903
_shelx_fab_checksum              61081
_olex2_submission_special_instructions 'No special instructions were received'