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_7156033
_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 H19 F N2 O3 S2'
_chemical_formula_sum            'C23 H19 F N2 O3 S2'
_chemical_formula_weight         454.52
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_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
_audit_creation_date             2017-01-13
_audit_creation_method
;
Olex2 1.2
(compiled 2017.01.04 svn.r3372 for OlexSys, GUI svn.r5289)
;
_audit_update_record
;
2017-07-21 deposited with the CCDC.
2017-12-12 downloaded from the CCDC.
;
_cell_angle_alpha                90.0
_cell_angle_beta                 105.076(10)
_cell_angle_gamma                90.0
_cell_formula_units_Z            4
_cell_length_a                   14.9465(16)
_cell_length_b                   9.9560(8)
_cell_length_c                   14.9447(12)
_cell_measurement_reflns_used    5872
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.5387
_cell_measurement_theta_min      2.8028
_cell_volume                     2147.3(4)
_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, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean 5.1796
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
  1 omega  -48.00   42.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -12.7965   85.0000   26.0000 90

  2 omega  -87.00   16.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -12.7965  -77.0000  150.0000 103

  3 omega  -45.00   38.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -12.7965   85.0000  -88.0000 83
;
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0394956000
_diffrn_orient_matrix_UB_12      -0.0356027000
_diffrn_orient_matrix_UB_13      0.0051602000
_diffrn_orient_matrix_UB_21      0.0209210000
_diffrn_orient_matrix_UB_22      -0.0614234000
_diffrn_orient_matrix_UB_23      -0.0075468000
_diffrn_orient_matrix_UB_31      0.0205682000
_diffrn_orient_matrix_UB_32      -0.0057389000
_diffrn_orient_matrix_UB_33      0.0482600000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0434
_diffrn_reflns_av_unetI/netI     0.0391
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            12822
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.348
_diffrn_reflns_theta_min         3.435
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.284
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90718
_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    1.403
_exptl_crystal_description       block
_exptl_crystal_F_000             944
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.36
_refine_diff_density_max         0.206
_refine_diff_density_min         -0.290
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     282
_refine_ls_number_reflns         3906
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0580
_refine_ls_R_factor_gt           0.0441
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0496P)^2^+0.5528P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1048
_refine_ls_wR_factor_ref         0.1151
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3096
_reflns_number_total             3906
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7ob02597a2.cif
_cod_data_source_block           170113_mfh_451_132_3
_cod_original_cell_volume        2147.3(2)
_cod_database_code               7156033
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         'c10 h10 n2 o8 s1 f1'
_cell_oxdiff_angle_alpha         90.036(5)
_cell_oxdiff_angle_beta          105.125(5)
_cell_oxdiff_angle_gamma         90.039(5)
_cell_oxdiff_length_a            14.9342(10)
_cell_oxdiff_length_b            9.9581(6)
_cell_oxdiff_length_c            14.9572(8)
_cell_oxdiff_measurement_reflns_used 5633
_cell_oxdiff_volume              2147.3(2)
_shelx_estimated_absorpt_t_max   0.905
_shelx_estimated_absorpt_t_min   0.876
_reflns_odcompleteness_completeness 99.74
_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.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C10(H10), C11(H11), C12(H12), C13(H13),
 C14(H14), C18(H18), C19(H19), C21(H21), C22(H22)
2.b Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C23(H23A,H23B,H23C)
;
_shelx_res_checksum              14738
_olex2_submission_special_instructions 'No special instructions were received'