Unusual hydrate stabilization in the two-dimensional layered structure of quinacrinium bis(2-carboxy-4,5-dichlorobenzoate) tetrahydrate, a proton-transfer compound of the drug quinacrine
Smith, Graham; Wermuth, Urs D.; Sagatys, Dalius S.; Acta Crystallographica Section C 65 (2009) o131–o133; doi:10.1107/S0108270109006702

data_2017043
_publ_section_title
;
 Unusual hydrate stabilization in the two-dimensional layered structure
 of quinacrinium bis(2-carboxy-4,5-dichlorobenzoate) tetrahydrate, a
 proton-transfer compound of the drug quinacrine
;
_journal_coeditor_code           GA3117
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o131
_journal_page_last               o133
_journal_paper_doi               10.1107/S0108270109006702
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C23 H32 Cl N3 O 2+ , 2C8 H3 Cl2 O4 - , 4H2 O'
_chemical_formula_moiety         'C23 H32 Cl N3 O 2+ , 2C8 H3 Cl2 O4 - , 4H2 O'
_chemical_formula_sum            'C39 H46 Cl5 N3 O13'
_chemical_formula_weight         942.04
_chemical_melting_point          343
_chemical_name_common
'quinacrinium bis(2-carboxy-4,5-dichlorobenzoate) tetrahydrate'
_chemical_name_systematic
;
[4-(6-chloro-2-methoxyacridin-10-ium-9-ylamino)pentyl]diethylammonium
bis(2-carboxy-4,5-dichlorobenzoate) tetrahydrate
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                77.961(5)
_cell_angle_beta                 89.549(5)
_cell_angle_gamma                76.432(5)
_cell_formula_units_Z            2
_cell_length_a                   10.6392(6)
_cell_length_b                   11.6737(5)
_cell_length_c                   18.2030(12)
_cell_measurement_reflns_used    5030
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      32.41
_cell_measurement_theta_min      3.01
_cell_volume                     2147.4(2)
_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    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.958
_diffrn_measurement_device_type  'Oxford Diffraction Gemini-S 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  0.0567
_diffrn_reflns_av_sigmaI/netI    0.0810
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            14440
_diffrn_reflns_theta_full        30.44
_diffrn_reflns_theta_max         25.25
_diffrn_reflns_theta_min         3.00
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.405
_exptl_absorpt_correction_T_max  0.948
_exptl_absorpt_correction_T_min  0.909
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.457
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             980
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.700
_refine_diff_density_min         -0.430
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     593
_refine_ls_number_reflns         7444
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.008
_refine_ls_R_factor_all          0.1217
_refine_ls_R_factor_gt           0.0779
_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^)+(0.1124P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1774
_refine_ls_wR_factor_ref         0.1947
_reflns_number_gt                4778
_reflns_number_total             7444
_reflns_threshold_expression     I>2\s(I)
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_cod_data_source_block           I
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_cod_database_fobs_code          2017043