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_7050785
_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            'C7 H8 Br2'
_chemical_formula_weight         251.95
_chemical_melting_point_lt       233.15
_chemical_name_systematic
; 
Toluene/Dibromine Molecular Complex 1:1
;
_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
_cell_angle_alpha                79.761(3)
_cell_angle_beta                 80.887(3)
_cell_angle_gamma                85.556(4)
_cell_formula_units_Z            4
_cell_length_a                   5.5163(12)
_cell_length_b                   11.715(2)
_cell_length_c                   13.551(3)
_cell_measurement_reflns_used    6941
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      28
_cell_measurement_theta_min      2
_cell_volume                     849.8(3)
_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
;
eight omega-scans, frame range 0.3 deg, full sphere 
;
_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  0.0766
_diffrn_reflns_av_sigmaI/netI    0.0534
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            19282
_diffrn_reflns_theta_max         29.23
_diffrn_reflns_theta_min         1.54
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    9.454
_exptl_absorpt_correction_T_max  1.0
_exptl_absorpt_correction_T_min  0.056
_exptl_absorpt_correction_type   'Semi-empirical (SADABS procedure)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.969
_exptl_crystal_density_method    none
_exptl_crystal_description       'long prism grown along capillary'
_exptl_crystal_F_000             480
_exptl_crystal_size_max          7.0
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.900
_refine_diff_density_min         -1.151
_refine_diff_density_rms         0.151
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.037
_refine_ls_goodness_of_fit_obs   1.056
_refine_ls_hydrogen_treatment
;
riding and rotating model with Uiso=1.2Uiso/eq of an adjacent carbon atom
(1.5Uiso/eq for Me-hydrogens)
;
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         4350
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.115
_refine_ls_restrained_S_obs      1.056
_refine_ls_R_factor_all          0.0755
_refine_ls_R_factor_obs          0.0385
_refine_ls_shift/esd_max         -0.005
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0463P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1018
_refine_ls_wR_factor_obs         0.0803
_reflns_number_observed          3051
_reflns_number_total             4356
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            b110169m.txt
_cod_data_source_block           alexbsx
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' tag was changed to
'_chemical_melting_point_lt' since the value was specified 'less
than' ('<') a certain temperature. The value '< -40C' was changed to
'233.15' - it was converted from degrees Celsius(C) to Kelvins(K).

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 

The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.0463P)^2^+0.0000P] 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^)+(0.0463P)^2^+0.0000P] 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      P-1
_cod_database_code               7050785