A resonance-assisted intramolecular hydrogen bond in compounds containing 2-hydroxy-3,5-dinitrobenzoic acid and its various deprotonated forms: redetermination of several related structures
Fábry, Jan; Acta Crystallographica Section E 74 (2018) 1344–1357; doi:10.1107/S2056989018011544

data_2242599
_publ_section_title
;
 A resonance-assisted intramolecular hydrogen bond in compounds containing
 2-hydroxy-3,5-dinitrobenzoic acid and its various deprotonated forms:
 redetermination of several related structures
;
_journal_coeditor_code           SU5452
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              1344
_journal_page_last               1357
_journal_paper_doi               10.1107/S2056989018011544
_journal_volume                  74
_journal_year                    2018
_chemical_formula_iupac          'C9 H8 Cl2 N5 + , C7 H3 N2 O7 - , C3 H7 N O'
_chemical_formula_moiety         'C9 H8 Cl2 N5 +, C7 H3 N2 O7 -, C3 H7 N O'
_chemical_formula_sum            'C19 H18 Cl2 N8 O8'
_chemical_formula_weight         557.31
_chemical_name_common
;
Lamotriginium 3,5-dinitro-2-hydroxybenzoate <i>N</i>,<i>N</i>-dimethylformamide
monosolvate
;
_chemical_name_systematic
;
3,5-Diamino-6-(2,3-dichlorophenyl)-1,2,4-triazin-2-ium
3,5-dinitro-2-hydroxybenzoate <i>N</i>,<i>N</i>-dimethylformamide
monosolvate
;
_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   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                81.8580(10)
_cell_angle_beta                 71.8880(10)
_cell_angle_gamma                70.0090(10)
_cell_formula_units_Z            2
_cell_length_a                   10.0227(5)
_cell_length_b                   10.5507(5)
_cell_length_c                   12.5359(6)
_cell_measurement_reflns_used    6413
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      28.15
_cell_measurement_theta_min      2.25
_cell_volume                     1183.10(10)
_computing_cell_refinement
;
SAINT (Bruker, 2001)
;
_computing_data_collection
;
SMART (Bruker, 2001)
;
_computing_data_reduction
;
SAINT (Bruker, 2001)
;
_computing_structure_refinement
;
JANA2006 (Petricek et al., 2014)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.962
_diffrn_measurement_device       'Bruker SMART APEX CCD area-detector'
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area-detector'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0194
_diffrn_reflns_av_sigmaI/netI    0.0220
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            13936
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         28.01
_diffrn_reflns_theta_min         1.71
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.339
_exptl_absorpt_correction_T_max  0.97
_exptl_absorpt_correction_T_min  0.93
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2001)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.564
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             572
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.80
_refine_diff_density_min         -0.36
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   3.41
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_constraints    48
_refine_ls_number_parameters     340
_refine_ls_number_reflns         5507
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0649
_refine_ls_R_factor_gt           0.0559
_refine_ls_shift/su_max          0.0204
_refine_ls_shift/su_mean         0.0026
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     w=1/(\s^2^(I)+0.0004I^2^)
_refine_ls_weighting_scheme      sigma
_refine_ls_wR_factor_gt          0.1449
_refine_ls_wR_factor_ref         0.1473
_reflns_number_gt                4441
_reflns_number_total             5507
_reflns_threshold_expression     I>3\s(I)
_cod_data_source_file            su5452sup1.cif
_cod_data_source_block           QIQJAD
_cod_database_code               2242599