Molecular structures of the metastable charge-transfer complexes of benzene (and toluene) with bromine as the pre-reactive intermediates in electrophilic aromatic bromination
Vasilyev, Alexandr V.; Lindeman, Sergey V.; Kochi, Jay K.; New Journal of Chemistry 26 (2002) 582–; doi:10.1039/b110169m

data_7050784
_publ_section_title
;
 Molecular structures of the metastable charge-transfer complexes of
 benzene (and toluene) with bromine as the pre-reactive intermediates
 in electrophilic aromatic bromination
;
_journal_issue                   5
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              582
_journal_paper_doi               10.1039/b110169m
_journal_volume                  26
_journal_year                    2002
_chemical_compound_source        'chemical synthesis'
_chemical_formula_sum            'C6 H6 Br2'
_chemical_formula_weight         237.93
_chemical_melting_point          'below -15C'
_chemical_name_systematic
; 
Benzene/Dibromine Molecular Complex 1:1 
;
_space_group_IT_number           154
_symmetry_cell_setting           trigonal
_symmetry_space_group_name_Hall  'P 32 2"'
_symmetry_space_group_name_H-M   'P 32 2 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_formula_units_Z            3
_cell_length_a                   8.721(2)
_cell_length_b                   8.721(2)
_cell_length_c                   8.701(2)
_cell_measurement_reflns_used    4035
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      28.6
_cell_measurement_theta_min      2.6
_cell_volume                     573.1(2)
_computing_cell_refinement       'SAINT V6.01 (BrukerAXS, 1997-99)'
_computing_data_collection       'SMART V5.054 (BrukerAXS, 1997-98)'
_computing_data_reduction        'SAINT & SADABS V2.06 (Sheldrick, 2000)'
_computing_molecular_graphics    'XP V5.06 (BrukerAXS, 1997-99)'
_computing_publication_material  'SHELXL-93, XCIF V5.05 (BrukerAXS, 1997-99)'
_computing_structure_refinement  'SHELXL-93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      123(2)
_diffrn_measurement_device       'Siemens/Bruker SMART 1K'
_diffrn_measurement_method
;
omega-scan, frame range 0.3 deg, hemisphere + two additional phi-scans
;
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0482
_diffrn_reflns_av_sigmaI/netI    0.0187
_diffrn_reflns_limit_h_max       0
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            7294
_diffrn_reflns_theta_max         29.03
_diffrn_reflns_theta_min         2.70
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    10.508
_exptl_absorpt_correction_T_max  1.0
_exptl_absorpt_correction_T_min  0.11
_exptl_absorpt_correction_type   'Semi-empirical (SADABS procedure)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    2.068
_exptl_crystal_density_method    none
_exptl_crystal_description       'crystal grown along capillary'
_exptl_crystal_F_000             336
_exptl_crystal_size_max          7.0
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.4
_refine_diff_density_max         0.985
_refine_diff_density_min         -2.206
_refine_diff_density_rms         0.220
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.15(26)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.171
_refine_ls_goodness_of_fit_obs   1.180
_refine_ls_hydrogen_treatment
;
riding model with Uiso=1.2Uiso/eq of an adjacent carbon atom
;
_refine_ls_matrix_type           full
_refine_ls_number_parameters     22
_refine_ls_number_reflns         581
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.409
_refine_ls_restrained_S_obs      1.180
_refine_ls_R_factor_all          0.0759
_refine_ls_R_factor_obs          0.0634
_refine_ls_shift/esd_max         -0.002
_refine_ls_shift/esd_mean        0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0388P)^2^+8.9084P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1781
_refine_ls_wR_factor_obs         0.1438
_reflns_number_observed          549
_reflns_number_total             597
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            b110169m.txt
_cod_data_source_block           alexasx
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.0388P)^2^+8.9084P] where P=(Fo^2^+2Fc^2^)/3' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to
'w=1/[\s^2^(Fo^2^)+(0.0388P)^2^+8.9084P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_sg_symbol_H-M      P3(2)21
_cod_database_code               7050784