Proton-transfer compounds of isonipecotamide with the aromatic dicarboxylic acids 4-nitrophthalic, 4,5-dichlorophthalic, 5-nitroisophthalic and terephthalic acid
Smith, Graham; Wermuth, Urs D.; Acta Crystallographica Section C 67 (2011) o259–o264; doi:10.1107/S0108270111020518

data_2018161
_publ_section_title
;
 Proton-transfer compounds of isonipecotamide with the aromatic
 dicarboxylic acids 4-nitrophthalic, 4,5-dichlorophthalic,
 5-nitroisophthalic and terephthalic acid
;
_journal_coeditor_code           SU3064
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o259
_journal_page_last               o264
_journal_paper_doi               10.1107/S0108270111020518
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          '2C6 H13 N2 O8 + , C8 H4 O4 2- , 2H2 O'
_chemical_formula_moiety         'C8 H4 O4, 2(C6 H13 N2 O), 2(H2 O)'
_chemical_formula_sum            'C20 H34 N4 O8'
_chemical_formula_weight         458.51
_chemical_melting_point          531
_chemical_name_common            'isonipecotamide terephthalate dihydrate'
_chemical_name_systematic
;
bis(4-carbamoylpiperidinium) benzene-1,2-dicarboxylate dihydrate
;
_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           SHELXL97
_cell_angle_alpha                76.429(8)
_cell_angle_beta                 76.968(7)
_cell_angle_gamma                80.885(7)
_cell_formula_units_Z            1
_cell_length_a                   6.5099(5)
_cell_length_b                   7.7777(6)
_cell_length_c                   11.6865(12)
_cell_measurement_reflns_used    3616
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      28.70
_cell_measurement_theta_min      3.37
_cell_volume                     556.89(9)
_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    'PLATON (Spek, 2009)'
_computing_publication_material  'PLATON (Spek, 2009)'
_computing_structure_refinement
;
SHELXL97 (Sheldrick, 2008) within WinGX (Farrugia, 1999)
;
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Oxford Gemini-S CCD are-detector'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0236
_diffrn_reflns_av_sigmaI/netI    0.0259
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6562
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         3.39
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.106
_exptl_absorpt_correction_T_max  0.990
_exptl_absorpt_correction_T_min  0.965
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrysAlis PRO; Oxford Diffraction, 2009)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.367
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             246
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.234
_refine_diff_density_min         -0.160
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     169
_refine_ls_number_reflns         2177
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0473
_refine_ls_R_factor_gt           0.0337
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[\s^2^(Fo^2^)+(0.0583P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0885
_refine_ls_wR_factor_ref         0.0926
_reflns_number_gt                1746
_reflns_number_total             2177
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            su3064.cif
_cod_data_source_block           IV
_cod_database_code               2018161
_cod_database_fobs_code          2018161