Utilizing proton transfer to produce molecular salts in bromanilic acid substituted-pyridine molecular complexes – predictable synthons?
Thomas, Lynne H.; Adam, Martin S.; O'Neill, Andrew; Wilson, Chick C.; Acta Crystallographica Section C 69 (2013) 1279–1288; doi:10.1107/S0108270113029533

data_2019226
_publ_section_title
;
 Utilizing proton transfer to produce molecular salts in bromanilic acid
 substituted-pyridine molecular complexes -- predictable synthons?
;
_journal_coeditor_code           FM3015
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1279
_journal_page_last               1288
_journal_paper_doi               10.1107/S0108270113029533
_journal_volume                  69
_journal_year                    2013
_chemical_formula_iupac          '2C6 H8 N + , C6 Br2 O4 2-'
_chemical_formula_moiety         '2(C6 H8 N) +, C6 Br2 O4 2-'
_chemical_formula_sum            'C18 H16 Br2 N2 O4'
_chemical_formula_weight         484.15
_chemical_name_common
;
Bis(3-methylpyridinium) bromanilate
;
_chemical_name_systematic
;
Bis(3-picolinium) bromanilate
;
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 103.935(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.9526(7)
_cell_length_b                   9.6149(8)
_cell_length_c                   10.4275(8)
_cell_measurement_temperature    100(2)
_cell_volume                     871.17(12)
_computing_cell_refinement       'APEX2 (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_data_reduction        'APEX2 (Bruker, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (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  'Bruker APEXII CCD area-detector'
_diffrn_measurement_method       'CCD; rotation images'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0331
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            9784
_diffrn_reflns_theta_full        28.87
_diffrn_reflns_theta_max         28.87
_diffrn_reflns_theta_min         2.34
_exptl_absorpt_coefficient_mu    4.68
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.671438
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Blessing, 1995)'
_exptl_crystal_colour            purple
_exptl_crystal_density_diffrn    1.846
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             480
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.446
_refine_diff_density_min         -0.633
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     123
_refine_ls_number_reflns         2280
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.081
_refine_ls_R_factor_all          0.0288
_refine_ls_R_factor_gt           0.0232
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0286P)^2^+0.5432P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.0606
_reflns_number_gt                2018
_reflns_number_total             2280
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            fm3015.cif
_cod_data_source_block           ba3pic100k1121apr_0m
_cod_database_code               2019226