Energetic analysis of the molecular packing of 5,5'-dibromo-2,2'-bis[4-(methylsulfanyl)phenyl]-4,4'-bipyridine: the role of π–π and halogen interactions
Abboud, Mohamed; Mamane, Victor; Aubert, Emmanuel; Acta Crystallographica Section C 69 (2013) 56–60; doi:10.1107/S0108270112048196

data_2018744
_publ_section_title
;
 Energetic analysis of the molecular packing of
 5,5'-dibromo-2,2'-bis[4-(methylsulfanyl)phenyl]-4,4'-bipyridine: the role
 of \p--\p and halogen interactions
;
_journal_coeditor_code           FG3278
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              56
_journal_page_last               60
_journal_paper_doi               10.1107/S0108270112048196
_journal_volume                  69
_journal_year                    2013
_chemical_formula_iupac          'C24 H18 Br2 N2 S2'
_chemical_formula_moiety         'C24 H18 Br2 N2 S2'
_chemical_formula_sum            'C24 H18 Br2 N2 S2'
_chemical_formula_weight         558.34
_chemical_name_systematic
;
5,5'-Dibromo-2,2'-bis[4-(methylsulfanyl)phenyl]-4,4'-bipyridine
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 106.6480(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   21.4175(2)
_cell_length_b                   5.97790(10)
_cell_length_c                   17.6539(2)
_cell_measurement_reflns_used    18560
_cell_measurement_temperature    110(2)
_cell_measurement_theta_max      76.2623
_cell_measurement_theta_min      4.3067
_cell_volume                     2165.51(5)
_computing_cell_refinement       'CrysAlis PRO (Oxford Diffraction, 2009)'
_computing_data_collection       'CrysAlis PRO (Oxford Diffraction, 2009)'
_computing_data_reduction        'CrysAlis PRO (Oxford Diffraction, 2009)'
_computing_molecular_graphics    'Mercury (Macrae <i>et al.</i>, 2008)'
_computing_publication_material  'publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR92 (Altomare <i>et al.</i>, 1994)'
_diffrn_ambient_temperature      110(2)
_diffrn_detector_area_resol_mean 10.4508
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type
'Oxford SuperNova dual diffractometer with Atlas detector'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_source         'SuperNova (Cu) X-ray Source'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54180
_diffrn_reflns_av_R_equivalents  0.0189
_diffrn_reflns_av_sigmaI/netI    0.0246
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            21521
_diffrn_reflns_theta_full        76.46
_diffrn_reflns_theta_max         76.46
_diffrn_reflns_theta_min         4.31
_exptl_absorpt_coefficient_mu    6.658
_exptl_absorpt_correction_T_max  0.706
_exptl_absorpt_correction_T_min  0.338
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
[CrysAlis PRO (Oxford Diffraction, 2009), using a multifaceted crystal
model (Clark & Reid, 1995)]
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.713
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1112
_exptl_crystal_size_max          0.2480
_exptl_crystal_size_mid          0.1591
_exptl_crystal_size_min          0.0622
_refine_diff_density_max         0.351
_refine_diff_density_min         -0.332
_refine_ls_extinction_coef       0.00063(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     138
_refine_ls_number_reflns         2281
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0168
_refine_ls_R_factor_gt           0.0166
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[\s^2^(Fo^2^)+(0.0218P)^2^+2.9248P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0442
_refine_ls_wR_factor_ref         0.0443
_reflns_number_gt                2255
_reflns_number_total             2281
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            fg3278.cif
_cod_data_source_block           I
_cod_original_cell_volume        2165.52(5)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2018744
_cod_database_fobs_code          2018744