Low-dimensional hydrogen-bonded structures in the 1:1 and 1:2 proton-transfer compounds of 4,5-dichlorophthalic acid with the aliphatic Lewis bases triethylamine, diethylamine, <i>n</i>-butylamine and piperidine
Smith, Graham; Wermuth, Urs D.; Acta Crystallographica Section C 66 (2010) o374–o380; doi:10.1107/S0108270110022328

data_2017712
_publ_section_title
;
 Low-dimensional hydrogen-bonded structures in the 1:1 and 1:2
 proton-transfer compounds of 4,5-dichlorophthalic acid with the
 aliphatic Lewis bases triethylamine, diethylamine, <i>n</i>-butylamine
 and piperidine
;
_journal_coeditor_code           GD3347
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o374
_journal_page_last               o380
_journal_paper_doi               10.1107/S0108270110022328
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          '2C5 H12 N +, C8 H2 Cl2 O4 2-, H2 O'
_chemical_formula_moiety         '2(C5 H12 N +), C8 H2 Cl2 O4 2-, H2 O'
_chemical_formula_sum            'C18 H28 Cl2 N2 O5'
_chemical_formula_weight         423.32
_chemical_melting_point          405
_chemical_name_common
'piperidinium 4,5-dichlorophthalate monohydrate'
_chemical_name_systematic
;
bis(piperidinium) 4,5-dichlorobenzene-1,2-dicarboxylate monohydrate
;
_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           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 99.903(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.8481(10)
_cell_length_b                   10.5937(8)
_cell_length_c                   14.6129(10)
_cell_measurement_reflns_used    6842
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      28.76
_cell_measurement_theta_min      3.40
_cell_volume                     2111.8(3)
_computing_cell_refinement
'<i>CrysAlis PRO</i> (Oxford Diffraction, 2009)'
_computing_data_collection
'<i>CrysAlis PRO</i> (Oxford Diffraction, 2009)'
_computing_data_reduction
'<i>CrysAlis PRO</i> (Oxford Diffraction, 2009)'
_computing_molecular_graphics    '<i>PLATON</i> (Spek, 2009)'
_computing_publication_material  '<i>PLATON</i> (Spek, 2009)'
_computing_structure_refinement
'<i>SHELXL97</i> (Sheldrick, 2008) within <i>WinGX</i> (Farrugia, 1999)'
_computing_structure_solution    '<i>SHELXS97</i> (Sheldrick, 2008)'
_diffrn_ambient_temperature      200(2)
_diffrn_detector_area_resol_mean 16.077
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type
'Oxford Diffraction Gemini-S CCD-detector diffractometer'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0569
_diffrn_reflns_av_sigmaI/netI    0.0374
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            26626
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         3.42
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.338
_exptl_absorpt_correction_T_max  0.980
_exptl_absorpt_correction_T_min  0.701
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(<i>SADABS</i>; Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.332
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             896
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.258
_refine_diff_density_min         -0.290
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.957
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     268
_refine_ls_number_reflns         4805
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.957
_refine_ls_R_factor_all          0.0591
_refine_ls_R_factor_gt           0.0375
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0644P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0954
_refine_ls_wR_factor_ref         0.1032
_reflns_number_gt                3570
_reflns_number_total             4805
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            gd3347.cif
_cod_data_source_block           IV
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2017712
_cod_database_fobs_code          2017712