Copper-Catalyzed Intermolecular C-H Amination of (Hetero)arenes via Transient Unsymmetrical λ(3)-Iodanes.
Sokolovs, Igors; Lubriks, Dmitrijs; Suna, Edgars; Journal of the American Chemical Society 136 (2014) 6920–6928; doi:10.1021/ja502174d

data_4121758
_publ_section_title
;
 Copper-Catalyzed Intermolecular C-H Amination of (Hetero)arenes via
 Transient Unsymmetrical \l(3)-Iodanes.
;
_journal_issue                   19
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              6920
_journal_page_last               6928
_journal_paper_doi               10.1021/ja502174d
_journal_volume                  136
_journal_year                    2014
_chemical_compound_source        'Local laboratory'
_chemical_formula_moiety         'C21 H22 Br I N O2, C7 H7 O3 S '
_chemical_formula_sum            'C28 H29 Br I N O5 S'
_chemical_formula_weight         698.41
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           maXus
_cell_angle_alpha                90.00
_cell_angle_beta                 104.197(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.9499(5)
_cell_length_b                   13.1575(4)
_cell_length_c                   15.5683(7)
_cell_measurement_reflns_used    29351
_cell_measurement_temperature    173
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      0.9
_cell_volume                     2770.22(18)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       KappaCCD
_computing_data_reduction        'Denzo and Scalepak (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'Ortep (Johnson, 1976)'
_computing_publication_material  'maXus(Mackay et al., 1999)'
_computing_structure_refinement  'maXus(Mackay et al., 1999)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.99
_diffrn_measured_fraction_theta_max 0.99
_diffrn_measurement_device_type  'Bruker-Nonius KappaCCD'
_diffrn_measurement_method       '\f and \w scan'
_diffrn_orient_matrix_type       X=UH
_diffrn_orient_matrix_UB_11      -0.01654
_diffrn_orient_matrix_UB_12      -0.07207
_diffrn_orient_matrix_UB_13      0.00000
_diffrn_orient_matrix_UB_21      0.00000
_diffrn_orient_matrix_UB_22      0.00000
_diffrn_orient_matrix_UB_23      -0.07600
_diffrn_orient_matrix_UB_31      0.05897
_diffrn_orient_matrix_UB_32      -0.03020
_diffrn_orient_matrix_UB_33      0.00000
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           ' MoK\a'
_diffrn_radiation_wavelength_id  all
_diffrn_reflns_av_R_equivalents  0.037
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            11273
_diffrn_reflns_theta_full        27.5
_diffrn_reflns_theta_max         27.5
_diffrn_reflns_theta_min         2.7
_exptl_absorpt_coefficient_mu    2.712
_exptl_absorpt_correction_T_max  0.742
_exptl_absorpt_correction_T_min  0.683
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details
;
By Gaussian integration based on twelve indexed crystal faces (NUMABS;
Coppens, 1970)
;
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.675
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'Parallelepiped '
_exptl_crystal_F_000             1392
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_refine_diff_density_max         3.73
_refine_diff_density_min         -4.89
_refine_diff_density_rms         0.29
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.094
_refine_ls_goodness_of_fit_gt    1.133
_refine_ls_goodness_of_fit_ref   1.124
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    29
_refine_ls_number_parameters     334
_refine_ls_number_reflns         3735
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.124
_refine_ls_R_factor_gt           0.064
_refine_ls_shift/su_max          0.029
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef F^2^
_refine_ls_weighting_details     ' w = 1 / ( s^2^(Fo^2^) + 0.10000 * Fo^2^)'
_refine_ls_weighting_scheme      sigma
_refine_ls_wR_factor_all         0.128
_refine_ls_wR_factor_gt          0.114
_refine_ls_wR_factor_ref         0.114
_reflns_d_resolution_high        0.62
_reflns_d_resolution_low         1.93
_reflns_limit_h_max              18
_reflns_limit_h_min              0
_reflns_limit_k_max              17
_reflns_limit_k_min              0
_reflns_limit_l_max              19
_reflns_limit_l_min              -20
_reflns_number_gt                3752
_reflns_number_total             6335
_reflns_threshold_expression     'I> 3.00 sigma(I)'
_cod_data_source_file            ja502174d_si_002.cif
_cod_data_source_block           iodonium
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 

 Adding full bibliography for 4121758.cif.

The following automatic conversions were performed:

'_atom_sites_solution_hydrogens' value 'geom, diff' was changed to
'mixed'.

Automatic conversion script
Id: cif_fix_values 6452 2018-10-05 10:23:21Z andrius 
;
_cod_original_cell_volume        2770.2(2)
_cod_original_sg_symbol_H-M      'P 21/c        '
_cod_original_formula_sum        'C28 H29 Br I N O5 S '
_cod_database_code               4121758