Hydrogen bonding in 4-nitrobenzene-1,2-diamine and two hydrohalide salts
Geiger, David K.; Parsons, Dylan E.; Acta Crystallographica Section C 70 (2014) 681–688; doi:10.1107/S2053229614013485

data_2019593
_publ_section_title
;
 Hydrogen bonding in 4-nitrobenzene-1,2-diamine and two hydrohalide salts
;
_journal_coeditor_code           SK3544
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              681
_journal_page_last               688
_journal_paper_doi               10.1107/S2053229614013485
_journal_volume                  70
_journal_year                    2014
_chemical_formula_iupac          'C6 H8 N3 O2 +, Br -, H2 O'
_chemical_formula_moiety         'C6 H8 N3 O2 +, Br -, H2 O'
_chemical_formula_sum            'C6 H10 Br N3 O3'
_chemical_formula_weight         252.08
_chemical_name_common
'4-nitro-o-phenylene diamine hydrobromide monohydrate'
_chemical_name_systematic
;
2-Amino-4-nitroanilinium bromide monohydrate
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           45
_space_group_name_Hall           'I 2 -2c'
_space_group_name_H-M_alt        'I b a 2'
_symmetry_space_group_name_Hall  'I 2 -2c'
_symmetry_space_group_name_H-M   'I b a 2'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   14.352(2)
_cell_length_b                   20.086(3)
_cell_length_c                   6.4851(9)
_cell_measurement_reflns_used    3357
_cell_measurement_temperature    200.(2)
_cell_measurement_theta_max      24.6148
_cell_measurement_theta_min      2.8346
_cell_volume                     1869.5(5)
_computing_cell_refinement       'APEX2 (Bruker, 2013)'
_computing_data_collection       '<i>APEX2</i> (Bruker, 2013)'
_computing_data_reduction        'SAINT (Bruker, 2013)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL2013 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      200.(2)
_diffrn_detector_area_resol_mean 8.3330
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker SMART X2S benchtop'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  'doubly curved silicon crystal'
_diffrn_radiation_type           'Mo Ka'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0691
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            8617
_diffrn_reflns_theta_full        25.31
_diffrn_reflns_theta_max         25.31
_diffrn_reflns_theta_min         2.84
_exptl_absorpt_coefficient_mu    4.378
_exptl_absorpt_correction_T_max  0.81
_exptl_absorpt_correction_T_min  0.48
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2013)'
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_density_diffrn    1.791
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1008
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.396
_refine_diff_density_min         -0.341
_refine_ls_abs_structure_details
;
Flack <i>x</i> determined using 554 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons <i>et al.</i>, 2013)
;
_refine_ls_abs_structure_Flack   0.006(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.955
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         1695
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.954
_refine_ls_R_factor_all          0.0416
_refine_ls_R_factor_gt           0.0303
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0314P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0671
_refine_ls_wR_factor_ref         0.0709
_reflns_number_gt                1387
_reflns_number_total             1695
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            sk3544sup1.cif
_cod_data_source_block           III
_cod_depositor_comments
'Adding full bibliography for 2019591--2019593.cif.'
_cod_database_code               2019593
_cod_database_fobs_code          2019593
_shelx_hkl_checksum              77843
_shelx_res_checksum              24709