Zero-, one- and two-dimensional hydrogen-bonded structures in the 1:1 proton-transfer compounds of 4,5-dichlorophthalic acid with the monocyclic heteroaromatic Lewis bases 2-aminopyrimidine, nicotinamide and isonicotinamide
Smith, Graham; Wermuth, Urs D.; White, Jonathan M.; Acta Crystallographica Section C 65 (2009) o103–o107; doi:10.1107/S0108270109004405

data_2017005
_publ_section_title
;
 Zero-, one- and two-dimensional hydrogen-bonded structures in the 1:1
 proton-transfer compounds of 4,5-dichlorophthalic acid with the
 monocyclic heteroaromatic Lewis bases 2-aminopyrimidine, nicotinamide
 and isonicotinamide
;
_journal_coeditor_code           GD3270
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o103
_journal_page_last               o107
_journal_paper_doi               10.1107/S0108270109004405
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C4 H6 N3 +, C8 H3 Cl2 O4 -'
_chemical_formula_moiety         'C4 H6 N3 +, C8 H3 Cl2 O4 -'
_chemical_formula_sum            'C12 H9 Cl2 N3 O4'
_chemical_formula_weight         330.12
_chemical_melting_point          337
_chemical_name_common
'2-aminopyrimidinium hydrogen 4,5-dichlorophthalate'
_chemical_name_systematic
;
2-aminopyrimidininium 2-carboxy-4,5-dichlorobenzoate
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
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_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_cell_angle_beta                 100.527(5)
_cell_angle_gamma                109.473(5)
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_cell_length_b                   9.4413(4)
_cell_length_c                   10.8900(7)
_cell_measurement_reflns_used    3656
_cell_measurement_temperature    180(2)
_cell_measurement_theta_max      73.1630
_cell_measurement_theta_min      4.2083
_cell_volume                     650.51(7)
_computing_cell_refinement       'CrysAlis RED (Oxford Diffraction, 2008)'
_computing_data_collection       'CrysAlis CCD (Oxford Diffraction, 2008)'
_computing_data_reduction        'CrysAlis RED (Oxford Diffraction, 2008)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      180(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_device_type
'Oxford Diffraction Gemini-S Ultra CCD-detector'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Cu) X-ray tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0201
_diffrn_reflns_av_sigmaI/netI    0.0217
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            4955
_diffrn_reflns_theta_full        67.68
_diffrn_reflns_theta_max         73.32
_diffrn_reflns_theta_min         4.22
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    4.704
_exptl_absorpt_correction_T_max  0.750
_exptl_absorpt_correction_T_min  0.263
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.685
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             336
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.06
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_refine_diff_density_min         -0.268
_refine_ls_extinction_method     none
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_refine_ls_number_reflns         2542
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.093
_refine_ls_R_factor_all          0.0362
_refine_ls_R_factor_gt           0.0331
_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^)+(0.0638P)^2^+0.0923P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0929
_refine_ls_wR_factor_ref         0.0946
_reflns_number_gt                2300
_reflns_number_total             2542
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            gd3270.cif
_cod_data_source_block           I
_cod_original_cell_volume        650.50(7)
_cod_database_code               2017005
_cod_database_fobs_code          2017005