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_2242601
_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          'C8 H13 N2 O +, C7 H3 N2 O7 -, H2 O'
_chemical_formula_moiety         'C8 H13 N2 O +, C7 H3 N2 O7 -, H2 O'
_chemical_formula_sum            'C15 H18 N4 O9'
_chemical_formula_weight         398.33
_chemical_name_systematic
;
2-Isopropyl-6-methyl-4-oxo-3,4-dihydropyrimidin-1-ium
2-carboxy-4,6-dinitrophenolate monohydrate
;
_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           SHELXL-97
_cell_angle_alpha                89.727(2)
_cell_angle_beta                 76.771(2)
_cell_angle_gamma                76.930(2)
_cell_formula_units_Z            2
_cell_length_a                   6.6691(3)
_cell_length_b                   11.3831(4)
_cell_length_c                   12.2900(5)
_cell_measurement_reflns_used    6994
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      31.63
_cell_measurement_theta_min      2.44
_cell_volume                     883.62(6)
_computing_cell_refinement
;
SAINT (Bruker, 2009)
;
_computing_data_collection
;
APEX2 (Bruker, 2009)
;
_computing_data_reduction
;
SAINT (Bruker, 2009)
;
_computing_structure_refinement
;
JANA2006 (Petricek et al., 2014)
;
_computing_structure_solution
;
SHELXTL (Sheldrick, 2008)
;
_diffrn_ambient_temperature      100.00(10)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type
;
Bruker SMART APEXII CCD area-detector
;
_diffrn_measurement_method       '\f and \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  0.0297
_diffrn_reflns_av_sigmaI/netI    0.0293
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            17014
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         1.70
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.126
_exptl_absorpt_correction_T_max  0.9872
_exptl_absorpt_correction_T_min  0.9374
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2009)
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.497
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             416
_exptl_crystal_size_max          0.52
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.46
_refine_diff_density_min         -0.23
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.77
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_constraints    52
_refine_ls_number_parameters     258
_refine_ls_number_reflns         4061
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0552
_refine_ls_R_factor_gt           0.0378
_refine_ls_shift/su_max          0.0140
_refine_ls_shift/su_mean         0.0012
_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          0.0804
_refine_ls_wR_factor_ref         0.0855
_reflns_number_gt                3042
_reflns_number_total             4061
_reflns_threshold_expression     I>3\s(I)
_cod_data_source_file            su5452sup1.cif
_cod_data_source_block           VABZIJ
_cod_database_code               2242601