Anhydrous 1:1 proton-transfer compounds of isonipecotamide with picric acid and 3,5-dinitrosalicylic acid: 4-carbamoylpiperidinium 2,4,6-trinitrophenolate and two polymorphs of 4-carbamoylpiperidinium 2-carboxy-4,6-dinitrophenolate
Smith, Graham; Wermuth, Urs D.; Acta Crystallographica Section C 66 (2010) o609–o613; doi:10.1107/S010827011004672X

data_2017887
_publ_section_title
;
 Anhydrous 1:1 proton-transfer compounds of isonipecotamide with picric
 acid and 3,5-dinitrosalicylic acid: 4-carbamoylpiperidinium
 2,4,6-trinitrophenolate and two polymorphs of 4-carbamoylpiperidinium
 2-carboxy-4,6-dinitrophenolate
;
_journal_coeditor_code           FG3206
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o609
_journal_page_last               o613
_journal_paper_doi               10.1107/S010827011004672X
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C6 H13 N2 O +, C6 H2 N3 O7 -'
_chemical_formula_moiety         'C6 H13 N2 O +, C6 H2 N3 O7 -'
_chemical_formula_sum            'C12 H15 N5 O8'
_chemical_formula_weight         357.29
_chemical_melting_point          452
_chemical_name_common            'isonipocotamide picrate'
_chemical_name_systematic
;
4-carbamoylpiperidinium 2,4,6-trinitrophenolate
;
_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                 100.752(13)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.4426(11)
_cell_length_b                   13.7495(13)
_cell_length_c                   8.3662(15)
_cell_measurement_reflns_used    3090
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      28.81
_cell_measurement_theta_min      2.88
_cell_volume                     1519.2(3)
_computing_cell_refinement
'<i>CrysAlis PRO</i> (Oxford Diffraction, 2009)'
_computing_data_collection
'<i>CrysAlis PRO</i> (Oxford Diffraction, 2009)'
_computing_data_reduction        'CrysAlis PRO?'
_computing_molecular_graphics    '<i>PLATON</i> (Spek, 2009)'
_computing_publication_material  '<i>PLATON</i> (Spek, 2009)'
_computing_structure_refinement  '<i>SHELXL97</i> (Sheldrick, 2008)'
_computing_structure_solution    '<i>SHELXS97</i> (Sheldrick, 2008)'
_diffrn_ambient_temperature      200(2)
_diffrn_detector_area_resol_mean 16.0774
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type
'Oxford Diffraction Gemini-S Ultra CCD-detector diffractometer'
_diffrn_measurement_method       '\w scans'
_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  0.0335
_diffrn_reflns_av_sigmaI/netI    0.0319
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            10181
_diffrn_reflns_theta_full        26.0
_diffrn_reflns_theta_max         26.0
_diffrn_reflns_theta_min         2.89
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.133
_exptl_absorpt_correction_T_max  0.981
_exptl_absorpt_correction_T_min  0.950
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'(<i>CrysAlis PRO</i>; Oxford Diffraction, 2009)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.562
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.264
_refine_diff_density_min         -0.279
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.933
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     238
_refine_ls_number_reflns         3422
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.933
_refine_ls_R_factor_all          0.0530
_refine_ls_R_factor_gt           0.0359
_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^)+(0.0765P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1011
_refine_ls_wR_factor_ref         0.1070
_reflns_number_gt                2279
_reflns_number_total             2994
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            fg3206.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2017887
_cod_database_fobs_code          2017887