1,10-Phenanthrolin-1-ium 2-carboxy-4,5-dichlorobenzoate
Smith, Graham; Wermuth, Urs D.; White, Jonathan M.; Acta Crystallographica Section E 65 (2009) o2333–; doi:10.1107/S1600536809034448

data_2223375
_publ_section_title
;
 1,10-Phenanthrolin-1-ium 2-carboxy-4,5-dichlorobenzoate
;
_journal_coeditor_code           FL2261
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2333
_journal_paper_doi               10.1107/S1600536809034448
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C12 H9 N2 +, C8 H3 Cl2 O4 -'
_chemical_formula_moiety         'C12 H9 N2 +, C8 H3 Cl2 O4 -'
_chemical_formula_sum            'C20 H12 Cl2 N2 O4'
_chemical_formula_weight         415.22
_chemical_melting_point_gt       464
_chemical_melting_point_lt       465
_chemical_name_common
'1,10-phenanthrolinium hydrogen 4,5-dichlorophthalate'
_chemical_name_systematic
;
1,10-Phenanthrolin-1-ium 2-carboxy-4,5-dichlorobenzoate
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 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                 94.978(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   6.4598(11)
_cell_length_b                   7.3696(12)
_cell_length_c                   18.302(3)
_cell_measurement_reflns_used    3630
_cell_measurement_temperature    130(2)
_cell_measurement_theta_max      27.54
_cell_measurement_theta_min      2.23
_cell_volume                     868.0(2)
_computing_cell_refinement       '<i>SAINT</i> (Bruker, 2000)'
_computing_data_collection       '<i>SMART</i> (Bruker, 2000)'
_computing_data_reduction        '<i>SAINT</i> (Bruker, 1999)'
_computing_molecular_graphics    '<i>PLATON</i> (Spek, 2009)'
_computing_publication_material  '<i>PLATON</i> (Spek, 2009)'
_computing_structure_refinement  '<i>SHELXL97</i> (Sheldrick, 2008)'
_computing_structure_solution    '<i>SHELXS97</i> (Sheldrick, 2008)'
_diffrn_ambient_temperature      130(2)
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       '\f and \w'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0170
_diffrn_reflns_av_sigmaI/netI    0.0374
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            5464
_diffrn_reflns_theta_full        27.59
_diffrn_reflns_theta_max         27.59
_diffrn_reflns_theta_min         1.12
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.406
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_correction_T_min  0.81
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(<i>SADABS</i>; Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.589
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.302
_refine_diff_density_min         -0.187
_refine_ls_abs_structure_details 'Flack (1983), 1564 Friedel pairs'
_refine_ls_abs_structure_Flack   0.00(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     261
_refine_ls_number_reflns         3734
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0329
_refine_ls_R_factor_gt           0.0319
_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^)+(0.053P)^2^+0.0522P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0844
_refine_ls_wR_factor_ref         0.0853
_reflns_number_gt                3629
_reflns_number_total             3734
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            fl2261.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               2223375
_cod_database_fobs_code          2223375