Synthesis of N-Functionalized/NH-Multisubstituted Indoles, Thienopyrroles, Pyrroloindoles, and Pyrazolopyrroles via Sequential One-Pot Base-Mediated and Copper-Catalyzed Inter- and Intramolecular Amination of 2-[2-Bromo(het)aryl]-3-(het)aryl-3-(methylthio)acrylonitriles.
Vijay Kumar, S.; Saraiah, B.; Parameshwarappa, G.; Ila, H.; Verma, Girijesh K.; The Journal of organic chemistry 79 (2014) 7961–7978; doi:10.1021/jo501114a

data_4029869
_publ_section_title
;
 Synthesis of N-Functionalized/NH-Multisubstituted Indoles,
 Thienopyrroles, Pyrroloindoles, and Pyrazolopyrroles via Sequential
 One-Pot Base-Mediated and Copper-Catalyzed Inter- and Intramolecular
 Amination of
 2-[2-Bromo(het)aryl]-3-(het)aryl-3-(methylthio)acrylonitriles.
;
_journal_issue                   17
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              7961
_journal_page_last               7978
_journal_paper_doi               10.1021/jo501114a
_journal_volume                  79
_journal_year                    2014
_chemical_formula_moiety         'C19 H10 Cl F N2 O'
_chemical_formula_sum            'C19 H10 Cl F N2 O'
_chemical_formula_weight         336.74
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2014-07-25
_audit_creation_method
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Olex2 1.2
(compiled 2014.07.22 svn.r2960 for OlexSys, GUI svn.r4862)
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_cell_angle_alpha                90
_cell_angle_beta                 100.875(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.1675(3)
_cell_length_b                   12.4426(3)
_cell_length_c                   12.6642(3)
_cell_measurement_reflns_used    4156
_cell_measurement_temperature    105.00(10)
_cell_measurement_theta_max      27.4600
_cell_measurement_theta_min      3.2720
_cell_volume                     1573.38(7)
_computing_cell_refinement
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
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_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
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_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
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_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
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_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      105.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0419
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
  1 omega  -25.00   16.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.2100   37.0000  120.0000 41

  2 omega  -45.00   48.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       24.5538  -57.0000 -150.0000 93

  3 omega    3.00   94.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       24.5538   57.0000    0.0000 91
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Nova'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0646811000
_diffrn_orient_matrix_UB_12      0.0201263000
_diffrn_orient_matrix_UB_13      -0.0219224000
_diffrn_orient_matrix_UB_21      0.0105563000
_diffrn_orient_matrix_UB_22      0.0437299000
_diffrn_orient_matrix_UB_23      0.0365689000
_diffrn_orient_matrix_UB_31      0.0274328000
_diffrn_orient_matrix_UB_32      0.0305405000
_diffrn_orient_matrix_UB_33      -0.0378650000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0203
_diffrn_reflns_av_unetI/netI     0.0362
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            6542
_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         27.483
_diffrn_reflns_theta_min         2.615
_diffrn_source                   'Mova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.261
_exptl_absorpt_correction_T_max  0.935
_exptl_absorpt_correction_T_min  0.913
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
Numerical absorption correction based on gaussian integration over
            a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.422
_exptl_crystal_description
;
;
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.5749
_exptl_crystal_size_mid          0.3061
_exptl_crystal_size_min          0.3011
_refine_diff_density_max         0.298
_refine_diff_density_min         -0.326
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         3594
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0450
_refine_ls_R_factor_gt           0.0390
_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^)+(0.0387P)^2^+0.5973P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0900
_refine_ls_wR_factor_ref         0.0954
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3196
_reflns_number_total             3594
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo501114a_si_003.cif
_cod_data_source_block           6d
_cod_depositor_comments
'Adding full bibliography for 4029867--4029869.cif.'
_cod_original_cell_volume        1573.39(7)
_cod_database_code               4029869
_shelxl_version_number           2014-1
_chemical_oxdiff_formula         'c18 h10 n2 cl1 f1 o1'
_chemical_oxdiff_usercomment     105K
_reflns_odcompleteness_completeness 99.76
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C10(H10), C2(H2), C6(H6), C7(H7), C18(H18), C20(H20),
 C19(H19), C9(H9)
;
_shelx_res_checksum              55481
_shelx_hkl_checksum              27748
_olex2_submission_special_instructions 'No special instructions were received'