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_2017710
_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          'C4 H12 N +, C8 H3 Cl2 O4 -'
_chemical_formula_moiety         'C4 H12 N +, C8 H3 Cl2 O4 -'
_chemical_formula_sum            'C12 H15 Cl2 N O4'
_chemical_formula_weight         308.14
_chemical_melting_point          443
_chemical_name_common            'diethylaminium hydrogen 4,5-dichlorophthalate'
_chemical_name_systematic
;
diethylaminium 2-carboxy-4,5-dichlorobenzoate
;
_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                 104.580(14)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.9588(13)
_cell_length_b                   9.9042(11)
_cell_length_c                   17.062(3)
_cell_measurement_reflns_used    2315
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      32.40
_cell_measurement_theta_min      2.90
_cell_volume                     1465.2(4)
_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_measured_fraction_theta_full 0.973
_diffrn_measured_fraction_theta_max 0.973
_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  0.0222
_diffrn_reflns_av_sigmaI/netI    0.0284
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            5638
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.95
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.451
_exptl_absorpt_correction_T_max  0.980
_exptl_absorpt_correction_T_min  0.926
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(<i>SADABS</i>; Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.392
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.379
_refine_diff_density_min         -0.260
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     184
_refine_ls_number_reflns         2802
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0507
_refine_ls_R_factor_gt           0.0373
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0641P)^2^+0.1213P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1027
_refine_ls_wR_factor_ref         0.1062
_reflns_number_gt                2159
_reflns_number_total             2802
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            gd3347.cif
_cod_data_source_block           II
_cod_original_cell_volume        1465.2(3)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2017710
_cod_database_fobs_code          2017710