Hydrogen bonding in the anhydrous 1:1 proton-transfer compounds of isonipecotamide with nitro-substituted benzoic acids: the salts of the three isomeric mononitrobenzoic acids and of 3,5-dinitrobenzoic acid
Smith, Graham; Wermuth, Urs D.; Acta Crystallographica Section C 66 (2010) o614–o618; doi:10.1107/S0108270110045750

data_2017907
_publ_section_title
;
 Hydrogen bonding in the anhydrous 1:1 proton-transfer compounds of
 isonipecotamide with nitro-substituted benzoic acids: the salts of the
 three isomeric mononitrobenzoic acids and of 3,5-dinitrobenzoic acid
;
_journal_coeditor_code           SU3056
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o614
_journal_page_last               o618
_journal_paper_doi               10.1107/S0108270110045750
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C6 H13 N2 O + , C7 H4 N O4 -'
_chemical_formula_moiety         'C6 H13 N2 O +, C7 H4 N O4 -'
_chemical_formula_sum            'C13 H17 N3 O5'
_chemical_formula_weight         295.30
_chemical_melting_point          452
_chemical_name_common            'isonipecotamide 3-nitrobenzoate'
_chemical_name_systematic
;
4-carbamoylpiperidinium 3-nitrobenzoate
;
_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           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 115.410(13)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.2504(15)
_cell_length_b                   6.8276(5)
_cell_length_c                   15.4580(17)
_cell_measurement_reflns_used    3622
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      28.76
_cell_measurement_theta_min      3.15
_cell_volume                     1358.5(3)
_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    'SIR92 (Altomare <i>et al.</i>, 1994)'
_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 Ultra CCD area-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  0.0260
_diffrn_reflns_av_sigmaI/netI    0.0299
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            9250
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         3.17
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.112
_exptl_absorpt_correction_T_max  0.980
_exptl_absorpt_correction_T_min  0.948
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrysAlis Pro; Oxford Diffraction, 2009)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.444
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.209
_refine_diff_density_min         -0.199
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     206
_refine_ls_number_reflns         2669
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0584
_refine_ls_R_factor_gt           0.0379
_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^)+(0.0550P)^2^ + 0.0538P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0877
_refine_ls_wR_factor_ref         0.0931
_reflns_number_gt                1982
_reflns_number_total             2669
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            su3056.cif
_cod_data_source_block           II
_cod_original_cell_volume        1358.5(2)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2017907
_cod_database_fobs_code          2017907