The three-dimensional hydrogen-bonded framework structure in the 1:1 proton-transfer compound of the drug quinacrine with 5-sulfosalicylic acid
Smith, Graham; Wermuth, Urs D.; Acta Crystallographica Section C 64 (2008) o428–o430; doi:10.1107/S0108270108020313

data_2016702
_publ_section_title
;
 The three-dimensional hydrogen-bonded framework structure in the 1:1
 proton-transfer compound of the drug quinacrine with 5-sulfosalicylic
 acid
;
_journal_coeditor_code           DN3093
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o428
_journal_page_last               o430
_journal_paper_doi               10.1107/S0108270108020313
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          'C23 H32 Cl N3 O 2+ , C7 H4 O6 S 2- , 2H2 O'
_chemical_formula_moiety         'C23 H32 Cl N3 O 2+ , C7 H4 O6 S 2- , 2H2 O'
_chemical_formula_sum            'C30 H40 Cl N3 O9 S'
_chemical_formula_weight         654.17
_chemical_melting_point          523
_chemical_name_common            'quinacrine 5-sulfosalicylate dihydrate'
_chemical_name_systematic
;
6-chloro-9-[(4-diethylammonio-2-methylbutyl)amino]-2-methoxyacridinium
3-carboxylato-4-hydroxybenzenesulfonate dihydrate
;
_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                 99.966(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.1753(3)
_cell_length_b                   30.8461(7)
_cell_length_c                   10.3671(2)
_cell_measurement_reflns_used    9373
_cell_measurement_temperature    297(2)
_cell_measurement_theta_max      28.92
_cell_measurement_theta_min      2.90
_cell_volume                     3204.80(14)
_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, 2003)'
_computing_publication_material  'PLATON (Spek, 2003)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR92 (Altomare <i>et al.</i>,  1994)'
_diffrn_ambient_temperature      297(2)
_diffrn_measured_fraction_theta_full 0.966
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measurement_device_type
'Oxford Diffraction Gemini-S Ultra CCD detector'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0485
_diffrn_reflns_av_sigmaI/netI    0.0642
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       36
_diffrn_reflns_limit_k_min       -36
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            29865
_diffrn_reflns_theta_full        25.0
_diffrn_reflns_theta_max         25.0
_diffrn_reflns_theta_min         2.9
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.241
_exptl_absorpt_correction_T_max  0.960
_exptl_absorpt_correction_T_min  0.906
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.356
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1384
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.260
_refine_diff_density_min         -0.260
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.986
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     433
_refine_ls_number_reflns         5455
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.986
_refine_ls_R_factor_all          0.0778
_refine_ls_R_factor_gt           0.0399
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[\s^2^(Fo^2^)+(0.0552P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0909
_refine_ls_wR_factor_ref         0.1001
_reflns_number_gt                3568
_reflns_number_total             5455
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            dn3093.cif
_cod_data_source_block           I
_cod_original_cell_volume        3204.81(14)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2016702
_cod_database_fobs_code          2016702