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_2019231
_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          'C6 H7 Br N + , C6 H Br2 O4 -'
_chemical_formula_moiety         'C6 H7 Br N +, C6 H Br2 O4 -'
_chemical_formula_sum            'C12 H8 Br3 N O4'
_chemical_formula_weight         469.91
_chemical_name_systematic
;
3-Bromo-4-methylpyridinium bromanilate
;
_space_group_IT_number           14
_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
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 95.802(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.2229(4)
_cell_length_b                   5.5760(2)
_cell_length_c                   24.5300(9)
_cell_measurement_temperature    100(2)
_cell_volume                     1391.12(9)
_computing_cell_refinement       'APEX2 (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_data_reduction        'APEX2 (Bruker, 2009)'
_computing_structure_refinement  'SHELXL2013 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.99
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_device_type  'Bruker APEXII CCD area-detector'
_diffrn_measurement_method       'CCD; rotation images'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0571
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            19916
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.153
_diffrn_reflns_theta_min         1.669
_exptl_absorpt_coefficient_mu    8.710
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.498695
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Blessing, 1995)'
_exptl_crystal_colour            purple
_exptl_crystal_density_diffrn    2.244
_exptl_crystal_description       block
_exptl_crystal_F_000             896
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_refine_diff_density_max         1.233
_refine_diff_density_min         -1.128
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         4796
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0739
_refine_ls_R_factor_gt           0.0412
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0482P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1013
_reflns_number_gt                3311
_reflns_number_total             4796
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            fm3015.cif
_cod_data_source_block           ba_3br4mepyr
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2019231