Copper-Mediated Multiple C–H Functionalization of AromaticN-Heterocycles: Bromoamination of Indoles and Pyrroles
John, Alex; Nicholas, Kenneth M.; Organometallics 31 (2012) 7914–; doi:10.1021/om300553b

data_4079180
_publ_section_title
;
 Copper-Mediated Multiple C--H Functionalization of
 AromaticN-Heterocycles: Bromoamination of Indoles and Pyrroles
;
_journal_issue                   22
_journal_name_full               Organometallics
_journal_page_first              7914
_journal_paper_doi               10.1021/om300553b
_journal_volume                  31
_journal_year                    2012
_chemical_formula_moiety         'C22 H17 Br N2'
_chemical_formula_sum            'C22 H17 Br N2'
_chemical_formula_weight         389.29
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_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_method           SHELXL-97
_cell_angle_alpha                101.861(7)
_cell_angle_beta                 91.029(7)
_cell_angle_gamma                97.388(6)
_cell_formula_units_Z            4
_cell_length_a                   8.590(3)
_cell_length_b                   9.837(3)
_cell_length_c                   21.360(7)
_cell_measurement_reflns_used    7057
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.23
_cell_measurement_theta_min      2.39
_cell_volume                     1749.9(10)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'SMART (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'CCD Bruker APEX'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0638
_diffrn_reflns_av_sigmaI/netI    0.0771
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            17034
_diffrn_reflns_theta_full        25.25
_diffrn_reflns_theta_max         25.30
_diffrn_reflns_theta_min         0.98
_exptl_absorpt_coefficient_mu    2.355
_exptl_absorpt_correction_T_max  0.6376
_exptl_absorpt_correction_T_min  0.4105
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2001)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.478
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.41
_exptl_crystal_size_min          0.21
_refine_diff_density_max         1.190
_refine_diff_density_min         -0.829
_refine_diff_density_rms         0.117
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     451
_refine_ls_number_reflns         6369
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.088
_refine_ls_R_factor_all          0.0840
_refine_ls_R_factor_gt           0.0602
_refine_ls_shift/su_max          0.009
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.1000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1651
_refine_ls_wR_factor_ref         0.1754
_reflns_number_gt                4725
_reflns_number_total             6369
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            om300553b_si_002.cif
_cod_data_source_block           12009
_cod_depositor_comments
;
The following automatic conversions were performed:

data name '_iucr_refine_instruction_details' was replaced with
'_iucr_refine_instructions_details' as specified in the replacement
file 'data/replacement-values/replacement_tags.lst'.

Automatic conversion script
Id: cif_correct_tags 9268 2022-04-12 08:56:07Z antanas 
;
_cod_original_cell_volume        1749.8(10)
_cod_database_code               4079180