C2/C4 Regioselective Heteroarylation of Indoles by Tuning C–H Metalation Modes
Chen, Shuyou; Zhang, Min; Su, Rongchuan; Chen, Xingyu; Feng, Boya; Yang, Yudong; You, Jingsong; ACS Catalysis 9 (2019) 6372–; doi:10.1021/acscatal.9b01273

data_4514795
_publ_section_title
;
 C2/C4 Regioselective Heteroarylation of Indoles by Tuning C--H Metalation
 Modes
;
_journal_issue                   7
_journal_name_full               'ACS Catalysis'
_journal_page_first              6372
_journal_paper_doi               10.1021/acscatal.9b01273
_journal_volume                  9
_journal_year                    2019
_chemical_formula_moiety         'C19 H21 N O S'
_chemical_formula_sum            'C19 H21 N O S'
_chemical_formula_weight         311.43
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2017-06-07
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   10.7285(2)
_cell_length_b                   17.9511(7)
_cell_length_c                   18.0222(6)
_cell_measurement_reflns_used    3212
_cell_measurement_temperature    296.31(10)
_cell_measurement_theta_max      72.3400
_cell_measurement_theta_min      5.3600
_cell_volume                     3470.87(19)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      296.31(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_details
;
  1 omega    2.00   29.00   1.0000    3.3200
omega____ theta____ kappa____ phi______ frames
    -       36.2921   91.0000   64.6159 27

  2 omega  -31.00   63.00   1.0000    3.3200
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -77.0000 -180.0000 94

  3 omega    1.00   75.00   1.0000    3.3200
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -99.0000  -30.0000 74

  4 omega    2.00   29.00   1.0000    3.3200
omega____ theta____ kappa____ phi______ frames
    -       36.2921   91.0000  138.2828 27

  5 omega   20.00  104.00   1.0000    3.3200
omega____ theta____ kappa____ phi______ frames
    -       36.2921   57.0000  -30.0000 84

  6 omega  -33.00   55.00   1.0000    3.3200
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -38.0000   60.0000 88

  7 omega   38.00  116.00   1.0000   13.2700
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000  -30.0000 78

  8 omega   39.00  109.00   1.0000   13.2700
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000 -180.0000 70

  9 omega   38.00   91.00   1.0000   13.2700
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   90.0000 53

 10 omega   40.00  144.00   1.0000   13.2700
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -15.0000  -60.0000 104
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Gemini, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0072527000
_diffrn_orient_matrix_UB_12      0.0092104000
_diffrn_orient_matrix_UB_13      -0.0848729000
_diffrn_orient_matrix_UB_21      -0.0130253000
_diffrn_orient_matrix_UB_22      -0.0849571000
_diffrn_orient_matrix_UB_23      -0.0095917000
_diffrn_orient_matrix_UB_31      -0.1427589000
_diffrn_orient_matrix_UB_32      0.0082910000
_diffrn_orient_matrix_UB_33      -0.0033998000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0491
_diffrn_reflns_av_unetI/netI     0.0377
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            9697
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.551
_diffrn_reflns_theta_min         4.908
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.652
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.56285
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.192
_exptl_crystal_description       needle
_exptl_crystal_F_000             1328
_exptl_crystal_size_max          0.75
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.661
_refine_diff_density_min         -0.357
_refine_diff_density_rms         0.115
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     204
_refine_ls_number_reflns         3371
_refine_ls_number_restraints     48
_refine_ls_restrained_S_all      1.148
_refine_ls_R_factor_all          0.1103
_refine_ls_R_factor_gt           0.0865
_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^)+(0.1629P)^2^+1.3091P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2504
_refine_ls_wR_factor_ref         0.2749
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2295
_reflns_number_total             3371
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs9b01273_si_002.cif
_cod_data_source_block           yjs-csy-001
_cod_original_cell_volume        3470.9(2)
_cod_database_code               4514795
_shelx_shelxl_version_number     2014/7
_reflns_odcompleteness_completeness 99.60
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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. Rigid bond restraints
 C00A, C00K, C00M, C00L
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.001
3. Uiso/Uaniso restraints and constraints
C00A \\sim C00K \\sim C00M \\sim C00L: within 2A with sigma of 0.01 and sigma
for terminal atoms of 0.02
Uanis(C00A) \\sim Ueq, Uanis(C00K) \\sim Ueq, Uanis(C00M) \\sim Ueq,
Uanis(C00L) \\sim Ueq: with sigma of 0.001 and sigma for terminal atoms of 0.002
4.a Aromatic/amide H refined with riding coordinates:
 C008(H008), C00C(H00C), C00D(H00D), C00E(H00E), C00F(H00F), C00G(H00G)
4.b Idealised Me refined as rotating group:
 C00I(H00A,H00B,H00H), C00J(H00I,H00J,H00K), C00K(H00L,H00M,H00N), C00L(H00O,
 H00P,H00Q), C00M(H00R,H00S,H00T)
;
_olex2_date_sample_data_collection 2017-06-06
_olex2_submission_special_instructions 'No special instructions were received'