N—H···O and O—H···O hydrogen-bonded supramolecular networks in 4-chloroanilinium, 2-hydroxyanilinium and 3-hydroxyanilinium hydrogen phthalates
Jagan, R.; Sivakumar, K.; Acta Crystallographica Section C 65 (2009) o414–o418; doi:10.1107/S0108270109025724

data_2017261
_publ_section_title
;
 N---H&#x00B7;&#x00B7;&#x00B7;O and O---H&#x00B7;&#x00B7;&#x00B7;O
 hydrogen-bonded supramolecular networks in 4-chloroanilinium,
 2-hydroxyanilinium and 3-hydroxyanilinium hydrogen phthalates
;
_journal_coeditor_code           SK3331
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o414
_journal_page_last               o418
_journal_paper_doi               10.1107/S0108270109025724
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C6 H8 N O +, C8 H5 O4 -'
_chemical_formula_moiety         'C6 H8 N O +, C8 H5 O4 -'
_chemical_formula_sum            'C14 H13 N O5'
_chemical_formula_weight         275.25
_chemical_name_systematic
;
3-hydroxyanilinium hydrogen phthalate
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 95.984(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.8924(3)
_cell_length_b                   8.1467(4)
_cell_length_c                   25.6509(15)
_cell_measurement_reflns_used    5610
_cell_measurement_temperature    292(2)
_cell_measurement_theta_max      30.62
_cell_measurement_theta_min      2.62
_cell_volume                     1224.63(11)
_computing_cell_refinement       'APEX2 and SAINT-Plus (Bruker, 2004)'
_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_data_reduction        'XPREP in SAINT-Plus (Bruker, 2004)'
_computing_molecular_graphics
'ORTEP3 for Windows (Farrugia, 1997) and Mercury (Macrae <i>et al.</i>,  2006)'
_computing_publication_material  'PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      292(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker KAPPA APEXII CCD diffractometer'
_diffrn_measurement_method       '\w and \f scan'
_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  0.0292
_diffrn_reflns_av_sigmaI/netI    0.0266
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            16385
_diffrn_reflns_theta_full        30.77
_diffrn_reflns_theta_max         30.77
_diffrn_reflns_theta_min         2.62
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.115
_exptl_absorpt_correction_T_max  0.9774
_exptl_absorpt_correction_T_min  0.8903
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 1999)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.493
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.344
_refine_diff_density_min         -0.185
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         3812
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0576
_refine_ls_R_factor_gt           0.0434
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
' w=1/[\s\^2\^(Fo\^2\^)+(0.0545P)\^2\^+0.2907P] where P=(Fo\^2\^+2Fc\^2\^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1074
_refine_ls_wR_factor_ref         0.1169
_reflns_number_gt                3009
_reflns_number_total             3812
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            sk3331.cif
_cod_data_source_block           III
_cod_original_sg_symbol_Hall     -P2ybc
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2017261
_cod_database_fobs_code          2017261