Hydrogen-bonded structures of the isomeric 2-, 3- and 4-carbamoylpyridinium hydrogen chloranilates
Gotoh, Kazuma; Nagoshi, Hirokazu; Ishida, Hiroyuki; Acta Crystallographica Section C 65 (2009) o273–o277; doi:10.1107/S010827010901525X

data_2017133
_publ_section_title
;
 Hydrogen-bonded structures of the isomeric 2-, 3- and
 4-carbamoylpyridinium hydrogen chloranilates
;
_journal_coeditor_code           GD3286
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o273
_journal_page_last               o277
_journal_paper_doi               10.1107/S010827010901525X
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C6 H7 N2 O + , C6 H Cl2 O4 -'
_chemical_formula_moiety         'C6 H7 N2 O + , C6 H Cl2 O4 -'
_chemical_formula_sum            'C12 H8 Cl2 N2 O5'
_chemical_formula_weight         331.11
_chemical_name_common
;
3-carbamoylpyridinium hydrogen chloranilate
;
_chemical_name_systematic
;
3-carbamoylpyridinium 2,5-dichloro-4-hydroxy-3,6-dioxocyclohexa-1,4-dienolate
;
_space_group_IT_number           7
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P -2yc'
_symmetry_space_group_name_H-M   'P 1 c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.0000
_cell_angle_beta                 114.8583(16)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            2
_cell_length_a                   9.9861(5)
_cell_length_b                   6.1438(3)
_cell_length_c                   11.6027(5)
_cell_measurement_reflns_used    5350
_cell_measurement_temperature    100.0(10)
_cell_measurement_theta_max      29.9
_cell_measurement_theta_min      3.3
_cell_volume                     645.90(5)
_computing_cell_refinement       'PROCESS-AUTO (Rigaku/MSC, 2004)'
_computing_data_collection       'PROCESS-AUTO (Rigaku/MSC, 2004)'
_computing_data_reduction        'CrystalStructure (Rigaku/MSC, 2004)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material
'CrystalStructure (Rigaku/MSC, 2004) and PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID II'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0187
_diffrn_reflns_av_sigmaI/netI    0.0250
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            5606
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         29.94
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.526
_exptl_absorpt_correction_T_max  0.959
_exptl_absorpt_correction_T_min  0.753
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(ABSCOR; Higashi, 1995)'
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    1.702
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platelet
_exptl_crystal_F_000             336.00
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.449
_refine_diff_density_min         -0.335
_refine_ls_abs_structure_details 'Flack (1983), with 1354 Friedel pairs'
_refine_ls_abs_structure_Flack   0.09(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     206
_refine_ls_number_reflns         3191
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.004
_refine_ls_R_factor_all          0.0382
_refine_ls_R_factor_gt           0.0328
_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^)+(0.1346P)^2^+0.0410P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1119
_refine_ls_wR_factor_ref         0.1492
_reflns_number_gt                2991
_reflns_number_total             3191
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            gd3286.cif
_cod_data_source_block           II
_cod_original_sg_symbol_H-M      'P c'
_cod_original_formula_sum        'C12 H8 Cl2 N2 O5 '
_cod_database_code               2017133
_cod_database_fobs_code          2017133