Three-dimensional hydrogen-bonded structures in the hydrated proton-transfer salts of isonipecotamide with the dicarboxylic oxalic and adipic acid homologues
Smith, Graham; Wermuth, Urs D.; Acta Crystallographica Section C 69 (2013) 1192–1195; doi:10.1107/S010827011302430X

data_2019165
_publ_section_title
;
 Three-dimensional hydrogen-bonded structures in the hydrated
 proton-transfer salts of isonipecotamide with the dicarboxylic oxalic and
 adipic acid homologues
;
_journal_coeditor_code           CU3038
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1192
_journal_page_last               1195
_journal_paper_doi               10.1107/S010827011302430X
_journal_volume                  69
_journal_year                    2013
_chemical_formula_iupac          'C6 H13 N2 O + , C2 H O4 - , 2H2 O'
_chemical_formula_moiety         'C6 H13 N2 O +, C2 H O4 -, 2(H2 O)'
_chemical_formula_sum            'C8 H18 N2 O7'
_chemical_formula_weight         254.24
_chemical_melting_point          366
_chemical_name_common            'isonipecotamide hydrogen oxalate dihydrate'
_chemical_name_systematic
;
4-Carbamoylpiperidinium hydrogen oxalate dihydrate
;
_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                 100.327(9)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.7265(5)
_cell_length_b                   28.646(2)
_cell_length_c                   7.4941(7)
_cell_measurement_reflns_used    4129
_cell_measurement_temperature    200.0(10)
_cell_measurement_theta_max      28.82
_cell_measurement_theta_min      3.48
_cell_volume                     1209.43(18)
_computing_cell_refinement       'CrysAlis PRO (Agilent, 2012)'
_computing_data_collection       'CrysAlis PRO (Agilent, 2012)'
_computing_data_reduction        'CrysAlis PRO (Agilent, 2012)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'PLATON (Spek, 2009)'
_computing_structure_refinement
;
SHELXL97 (Sheldrick, 2008) within WinGX (Farrugia, 2012)
;
_computing_structure_solution    'SIR92 (Altomare <i>et al.</i>, 1993)'
_diffrn_ambient_temperature      200.0(10)
_diffrn_detector_area_resol_mean 16.077
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0305
_diffrn_reflns_av_sigmaI/netI    0.0294
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       35
_diffrn_reflns_limit_k_min       -35
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            7562
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         3.49
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.122
_exptl_absorpt_correction_T_max  0.990
_exptl_absorpt_correction_T_min  0.893
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrysAlis PRO; Agilent, 2012)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.396
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.350
_refine_diff_density_min         -0.316
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2369
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0546
_refine_ls_R_factor_gt           0.0418
_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^)+(0.0648P)^2^+0.2236P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1056
_refine_ls_wR_factor_ref         0.1102
_reflns_number_gt                1888
_reflns_number_total             2369
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            cu3038.cif
_cod_data_source_block           I
_cod_original_cell_volume        1209.44(18)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2019165