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_2017888
_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 +, C7 H3 N2 O7 -'
_chemical_formula_moiety         'C6 H13 N2 O +, C7 H3 N2 O7 -'
_chemical_formula_sum            'C13 H16 N4 O8'
_chemical_formula_weight         356.30
_chemical_melting_point          475
_chemical_name_common
'isonipecotamide 3,5-dinitrosalicylate (polymorph 1)'
_chemical_name_systematic
;
4-carbamoylpiperidinium 2-carboxy-4,6-dinitrophenolate
;
_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                 118.196(14)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.7131(12)
_cell_length_b                   12.6450(11)
_cell_length_c                   11.8521(14)
_cell_measurement_reflns_used    5903
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      28.90
_cell_measurement_theta_min      3.09
_cell_volume                     1547.1(3)
_computing_cell_refinement
'<i>CrysAlis PRO</i> (Oxford Diffraction,  2009)'
_computing_data_collection
'<i>CrysAlis PRO</i> (Oxford Diffraction,  2009)'
_computing_data_reduction
'<i>CrysAlis PRO</i> (Oxford Diffraction,  2009)'
_computing_molecular_graphics    '<i>PLATON</i> (Spek, 2009)'
_computing_publication_material  '<i>PLATON</i> (Spek, 2009)'
_computing_structure_refinement
'SHELXL97 (Sheldrick, 2008) within <i>WinGX</i> (Farrugia, 1999)'
_computing_structure_solution    '<i>SIR92</i> (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 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  0.0329
_diffrn_reflns_av_sigmaI/netI    0.0208
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            19733
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         3.22
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.129
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_correction_T_min  0.93
_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    1.530
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.307
_refine_diff_density_min         -0.239
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     242
_refine_ls_number_reflns         3048
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0560
_refine_ls_R_factor_gt           0.0388
_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^)+(0.0505P)^2^+0.3254P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0921
_refine_ls_wR_factor_ref         0.0983
_reflns_number_gt                2456
_reflns_number_total             3048
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            fg3206.cif
_cod_data_source_block           II
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2017888
_cod_database_fobs_code          2017888