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_2018159
_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          'C6 H13 N2 O + , C8 H3 Cl2 O4 -'
_chemical_formula_moiety         'C6 H13 N2 O +, C8 H3 Cl2 O4 -'
_chemical_formula_sum            'C14 H16 Cl2 N2 O5'
_chemical_formula_weight         363.19
_chemical_name_common
'isonipecotamide hydrogen 4,5-dichlorophthalate'
_chemical_name_systematic
;
4-carbamoylpiperidinium 2-carboxy-4,5-dichlorobenzoate
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 92.479(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.6897(4)
_cell_length_b                   9.7392(5)
_cell_length_c                   24.1222(13)
_cell_measurement_reflns_used    8871
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      28.89
_cell_measurement_theta_min      3.14
_cell_volume                     1570.15(15)
_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 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Oxford Gemini S 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  0.0277
_diffrn_reflns_av_sigmaI/netI    0.0159
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            19231
_diffrn_reflns_theta_full        25.99
_diffrn_reflns_theta_max         25.99
_diffrn_reflns_theta_min         3.13
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.440
_exptl_absorpt_correction_T_max  0.980
_exptl_absorpt_correction_T_min  0.908
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrysAlis PRO; Oxford Diffraction, 2009)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.536
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.367
_refine_diff_density_min         -0.292
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.299
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     224
_refine_ls_number_reflns         3084
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.299
_refine_ls_R_factor_all          0.0531
_refine_ls_R_factor_gt           0.0460
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[\s^2^(Fo^2^)+(0.0177P)^2^+2.7340P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1108
_refine_ls_wR_factor_ref         0.1131
_reflns_number_gt                2777
_reflns_number_total             3084
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            su3064.cif
_cod_data_source_block           II
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2018159
_cod_database_fobs_code          2018159