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_2019230
_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          'C7 H10 N + , C6 H Br2 O4 -'
_chemical_formula_moiety         'C7 H10 N +, C6 H Br2 O4 -'
_chemical_formula_sum            'C13 H11 Br2 N O4'
_chemical_formula_weight         405.04
_chemical_name_common
;
3,5-Lutidinium bromanilate
;
_chemical_name_systematic
;
3,5-Dimethylpyridinium 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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 98.834(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.6766(5)
_cell_length_b                   10.4926(5)
_cell_length_c                   11.5221(5)
_cell_measurement_temperature    100(2)
_cell_volume                     1394.92(11)
_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 0.955
_diffrn_measured_fraction_theta_max 0.82
_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  0.0309
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            14020
_diffrn_reflns_theta_full        25
_diffrn_reflns_theta_max         31.54
_diffrn_reflns_theta_min         1.76
_exptl_absorpt_coefficient_mu    5.82
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.684360
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Blessing, 1995)'
_exptl_crystal_colour            purple
_exptl_crystal_density_diffrn    1.929
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.581
_refine_diff_density_min         -0.452
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.05
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         3817
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.05
_refine_ls_R_factor_all          0.0395
_refine_ls_R_factor_gt           0.0271
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[\s^2^(Fo^2^)+(0.0335P)^2^+0.6408P] where P = (Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.0666
_reflns_number_gt                3131
_reflns_number_total             3817
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            fm3015.cif
_cod_data_source_block           ba_35lut
_cod_database_code               2019230