Chemoselective Ullmann Coupling at Room Temperature: A Facile Access to 2-Aminobenzo[b]thiophenes
Janni, Manojkumar; Thriupathi, Annaram; Arora, Sahil; Peruncheralathan, Saravanan; Chem. Commun.  (2017) –; doi:10.1039/C7CC03273K

data_7120373
_publ_section_title
;
 Chemoselective Ullmann Coupling at Room Temperature: A Facile Access to
 2-Aminobenzo[b]thiophenes
;
_journal_name_full               'Chem. Commun.'
_journal_paper_doi               10.1039/C7CC03273K
_journal_year                    2017
_chemical_formula_moiety         'C15 H10 N2 S'
_chemical_formula_sum            'C15 H10 N2 S'
_chemical_formula_weight         250.31
_chemical_melting_point          135.0(10)
_chemical_name_systematic        2-anilino-3-cyanobenzo[b]thiophene
_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             2017-04-20
_audit_creation_method
;
Olex2 1.2-alpha
(compiled 2016.02.24 svn.r3266 for OlexSys, GUI svn.r5155)
;
_audit_update_record
;
2017-04-21 deposited with the CCDC.
2017-07-03 downloaded from the CCDC.
;
_cell_angle_alpha                74.773(5)
_cell_angle_beta                 83.574(5)
_cell_angle_gamma                81.477(5)
_cell_formula_units_Z            2
_cell_length_a                   3.905(5)
_cell_length_b                   12.317(5)
_cell_length_c                   13.486(5)
_cell_measurement_reflns_used    6962
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      19.069
_cell_measurement_theta_min      3.140
_cell_volume                     617.2(9)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT  A'
_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_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0443
_diffrn_reflns_av_unetI/netI     0.0726
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            6942
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.63
_diffrn_reflns_theta_min         1.57
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.243
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_correction_T_min  0.6554
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.347
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             260
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Hexane & Dichloromethane'
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.222
_refine_diff_density_min         -0.234
_refine_diff_density_rms         0.053
_refine_ls_extinction_coef       0.023(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     168
_refine_ls_number_reflns         2311
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.0923
_refine_ls_R_factor_gt           0.0448
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0619P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1007
_refine_ls_wR_factor_ref         0.1369
_reflns_number_gt                1376
_reflns_number_total             2311
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            c7cc03273k2.cif
_cod_data_source_block           s_peru_mj_513a_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '134-136' was changed to '135.0(10)'
- the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 
;
_cod_database_code               7120373
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C15(H15), C6(H6), C3(H3), C11(H11), C14(H14), C5(H5), C4(H4),
 C12(H12), C13(H13)
;
_olex2_submission_special_instructions 'No special instructions were received'