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_2017889
_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         'C7 H3 N2 O7, C6 H13 N2 O'
_chemical_formula_sum            'C13 H16 N4 O8'
_chemical_formula_weight         356.30
_chemical_melting_point          475
_chemical_name_common
'isonipecotamide 3,5-dinitrosalicylate: polymorph 2'
_chemical_name_systematic
;
4-carbamoylpiperidinium 2-carboxy-4,6-dinitrophenolate
;
_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                98.644(4)
_cell_angle_beta                 96.905(5)
_cell_angle_gamma                100.753(5)
_cell_formula_units_Z            4
_cell_length_a                   6.4628(4)
_cell_length_b                   10.2375(5)
_cell_length_c                   23.8964(12)
_cell_measurement_reflns_used    6525
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      26.32
_cell_measurement_theta_min      3.23
_cell_volume                     1517.65(15)
_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
;
<i>SHELXL97</i> (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_detector_area_resol_mean 16.0774
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0263
_diffrn_reflns_av_sigmaI/netI    0.0331
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_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            19052
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         3.23
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.131
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_correction_T_min  0.96
_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    1.559
_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          0.30
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.230
_refine_diff_density_min         -0.230
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.819
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     475
_refine_ls_number_reflns         5940
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.819
_refine_ls_R_factor_all          0.0598
_refine_ls_R_factor_gt           0.0387
_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^)+(0.0513P)^2^+0.9420P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0875
_refine_ls_wR_factor_ref         0.0948
_reflns_number_gt                4477
_reflns_number_total             5940
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            fg3206.cif
_cod_data_source_block           III
_cod_database_code               2017889
_cod_database_fobs_code          2017889