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_2242604
_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          'C7 H4 N2 O7, C12 H8 N2'
_chemical_formula_moiety         'C7 H4 N2 O7, C12 H8 N2'
_chemical_formula_sum            'C19 H12 N4 O7'
_chemical_formula_weight         408.33
_chemical_melting_point          471
_chemical_name_common
;
3,5-Dinitrosalicylic acid--phenazine (1/1)
;
_chemical_name_systematic
;
3,5-Dinitrosalicylic acid--phenazine (1/1)
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yab'
_symmetry_space_group_name_H-M   'P 1 21/a 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 96.395(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.8002(15)
_cell_length_b                   7.4029(16)
_cell_length_c                   16.0091(16)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      12
_cell_measurement_theta_min      5
_cell_volume                     1743.1(5)
_computing_cell_refinement
;
CAD-4 Software (Enraf-Nonius, 1989)
;
_computing_data_collection
;
CAD-4 Software (Enraf-Nonius, 1989)
;
_computing_data_reduction
;
Xtal3.5 (Hall et al., 1995)
;
_computing_structure_refinement
;
JANA2006 (Petricek et al., 2014)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Enraf-Nonius CAD-4'
_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  0.0559
_diffrn_reflns_av_sigmaI/netI    0.0791
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            8396
_diffrn_reflns_theta_full        27.97
_diffrn_reflns_theta_max         28.0
_diffrn_reflns_theta_min         1.50
_diffrn_standards_decay_%        2
_diffrn_standards_interval_count 150
_diffrn_standards_interval_time  90
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.122
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.556
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rhombic
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.26
_refine_diff_density_max         0.29
_refine_diff_density_min         -0.31
_refine_ls_extinction_coef       51E2(5)
_refine_ls_extinction_method
;
B-C type 1 Lorentzian isotropic (Becker & Coppens, 1974)
;
_refine_ls_goodness_of_fit_ref   1.08
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    40
_refine_ls_number_parameters     274
_refine_ls_number_reflns         4202
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1521
_refine_ls_R_factor_gt           0.0437
_refine_ls_shift/su_max          0.0057
_refine_ls_shift/su_mean         0.0006
_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          0.0681
_refine_ls_wR_factor_ref         0.0825
_reflns_number_gt                1587
_reflns_number_total             4202
_reflns_threshold_expression     I>3\s(I)
_cod_data_source_file            su5452sup1.cif
_cod_data_source_block           LUDFUL
_cod_original_sg_symbol_H-M      'P 21/a'
_cod_database_code               2242604