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_2019166
_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          '2C6 H13 N2 O + , C6 H8 O4 - , 2H2 O'
_chemical_formula_moiety         '2(C6 H13 N2 O +), C6 H8 O4 -, 2(H2 O)'
_chemical_formula_sum            'C18 H38 N4 O8'
_chemical_formula_weight         438.52
_chemical_melting_point          353
_chemical_name_common            'isonipecotamide adipate dihydrate'
_chemical_name_systematic
;
Bis(4-carbamoylpiperidinium) butane-1,4-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                75.336(5)
_cell_angle_beta                 81.763(5)
_cell_angle_gamma                78.448(5)
_cell_formula_units_Z            1
_cell_length_a                   5.8454(4)
_cell_length_b                   7.7696(5)
_cell_length_c                   13.0987(7)
_cell_measurement_reflns_used    3402
_cell_measurement_temperature    200.0(10)
_cell_measurement_theta_max      28.66
_cell_measurement_theta_min      3.49
_cell_volume                     561.16(6)
_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  0.0265
_diffrn_reflns_av_sigmaI/netI    0.0332
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            6679
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         3.50
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_T_max  0.983
_exptl_absorpt_correction_T_min  0.955
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrysAlis PRO; Agilent, 2012)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.298
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             238
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.196
_refine_diff_density_min         -0.164
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.979
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     160
_refine_ls_number_reflns         2204
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.979
_refine_ls_R_factor_all          0.0515
_refine_ls_R_factor_gt           0.0348
_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^)+(0.0527P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0829
_refine_ls_wR_factor_ref         0.0876
_reflns_number_gt                1683
_reflns_number_total             2204
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            cu3038.cif
_cod_data_source_block           II
_cod_original_cell_volume        561.17(6)
_cod_database_code               2019166