N—H···O, O—H···O hydrogen-bonded supramolecular sheet formation in the bis(2-aminoanilinium) fumarate, 3-methylanilinium hydrogen fumarate and 4-chloroanilinium hydrogen fumarate salts
Sathya, D.; Jagan, R.; Padmavathy, R.; Kumar, R. Mohan; Sivakumar, K.; Acta Crystallographica Section C 69 (2013) 904–909; doi:10.1107/S0108270113017629

data_2019106
_publ_section_title
;
 N---H&#x00B7;&#x00B7;&#x00B7;O, O---H&#x00B7;&#x00B7;&#x00B7;O
 hydrogen-bonded supramolecular sheet formation in the
 bis(2-aminoanilinium) fumarate, 3-methylanilinium hydrogen fumarate and
 4-chloroanilinium hydrogen fumarate salts
;
_journal_coeditor_code           UK3068
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              904
_journal_page_last               909
_journal_paper_doi               10.1107/S0108270113017629
_journal_volume                  69
_journal_year                    2013
_chemical_formula_iupac          'C7 H10 N + , C4 H3 O4 -'
_chemical_formula_moiety         'C7 H10 N +, C4 H3 O4 -'
_chemical_formula_sum            'C11 H13 N O4'
_chemical_formula_weight         223.22
_chemical_name_systematic
;
3-Methylanilinium hydrogen fumarate
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 92.611(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   9.4576(3)
_cell_length_b                   20.8915(6)
_cell_length_c                   10.8787(3)
_cell_measurement_reflns_used    5904
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      30.50
_cell_measurement_theta_min      2.36
_cell_volume                     2147.22(11)
_computing_cell_refinement       'APEX2 and SAINT (Bruker, 2004)'
_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_data_reduction        'SAINT and XPREP (Bruker, 2004)'
_computing_molecular_graphics
;
ORTEP-3 (Farrugia, 2012) and Mercury (Macrae <i>et al.</i>,
2008)
;
_computing_publication_material  'PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker Kappa APEXII CCD area-detector'
_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  0.0360
_diffrn_reflns_av_sigmaI/netI    0.0252
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            37301
_diffrn_reflns_theta_full        30.80
_diffrn_reflns_theta_max         30.80
_diffrn_reflns_theta_min         2.11
_exptl_absorpt_coefficient_mu    0.106
_exptl_absorpt_correction_T_max  0.9740
_exptl_absorpt_correction_T_min  0.9039
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2004)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.381
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             944
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.379
_refine_diff_density_min         -0.212
_refine_ls_extinction_coef       0.0060(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     322
_refine_ls_number_reflns         6714
_refine_ls_number_restraints     10
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0627
_refine_ls_R_factor_gt           0.0439
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[\s^2^(Fo^2^)+(0.0656P)^2^+0.4207P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1182
_refine_ls_wR_factor_ref         0.1303
_reflns_number_gt                5066
_reflns_number_total             6714
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            uk3068.cif
_cod_data_source_block           II
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2019106
_cod_database_fobs_code          2019106