Regioselective Csp(2)-H dual functionalization of indoles using hypervalent iodine(iii): bromo-amination via 1,3-migration of imides on indolyl(phenyl)iodonium imides.
Moriyama, Katsuhiko; Ishida, Kazuma; Togo, Hideo; Chemical communications (Cambridge, England) 51 (2015) 2273–2276; doi:10.1039/c4cc09077b

data_7116302
_publ_section_title
;
 Regioselective Csp(2)-H dual functionalization of indoles using
 hypervalent iodine(iii): bromo-amination via 1,3-migration of imides on
 indolyl(phenyl)iodonium imides.
;
_journal_issue                   12
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              2273
_journal_page_last               2276
_journal_paper_doi               10.1039/c4cc09077b
_journal_volume                  51
_journal_year                    2015
_chemical_formula_sum            'C35 H35 Cl6 I N2 O5 S2'
_chemical_formula_weight         967.37
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_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
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2014-09-08 deposited with the CCDC.
2014-12-16 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 97.187(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
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_cell_length_b                   9.5783(15)
_cell_length_c                   23.967(4)
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_cell_measurement_temperature    173
_cell_measurement_theta_max      23.95
_cell_measurement_theta_min      2.25
_cell_volume                     4157.5(12)
_computing_cell_refinement       'APEX2 (Bruker AXS, 2006)'
_computing_data_collection       'APEX2 (Bruker AXS, 2006)'
_computing_data_reduction        'SAINT (Bruker AXS, 2004)'
_computing_molecular_graphics    'XSHEL (Bruker AXS,2002)'
_computing_publication_material  'XCIF (Bruker AXS, 2001)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      173
_diffrn_detector_area_resol_mean 8.333
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_device_type  'Bruker APEXII CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
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_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            22389
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         27.56
_diffrn_reflns_theta_min         1.33
_exptl_absorpt_coefficient_mu    1.298
_exptl_absorpt_correction_T_max  0.8812
_exptl_absorpt_correction_T_min  0.6969
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
;
SADABS Sheldrick 1996
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.545
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             1944
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         2.669
_refine_diff_density_min         -1.029
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_refine_ls_extinction_method     none
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_refine_ls_matrix_type           full
_refine_ls_number_parameters     539
_refine_ls_number_reflns         9335
_refine_ls_number_restraints     24
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.1171
_refine_ls_R_factor_gt           0.0678
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1180P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1797
_refine_ls_wR_factor_ref         0.2139
_reflns_number_gt                5611
_reflns_number_total             9335
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4cc09077b2.cif
_cod_data_source_block           a130112mor2
_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/RSC/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 2935 2014-11-11 08:27:57Z andrius 

 Adding full bibliography for 7116301--7116305.cif.
;
_cod_original_cell_volume        4157.7(11)
_cod_original_sg_symbol_H-M      'P2(1)/n  '
_cod_database_code               7116302