Complexation of drug amifampridine with Cu(II), Zn(II) and Cd(II) ions, and its dimerization with the magic of Mn(II) salts. Potential anti-COVID-19 and anticancer activities.
Hajibabaei, Farshid; Movafagh, Samaneh Sanei; Salehzadeh, Sadegh; Gable, Robert William; Dalton transactions (Cambridge, England : 2003) 53 (2024) 1066–1086; doi:10.1039/d3dt03281g

data_7714722
_publ_section_title
;
 Complexation of drug amifampridine with Cu(II), Zn(II) and Cd(II) ions,
 and its dimerization with the magic of Mn(II) salts. Potential
 anti-COVID-19 and anticancer activities.
;
_journal_issue                   3
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              1066
_journal_page_last               1086
_journal_paper_doi               10.1039/d3dt03281g
_journal_volume                  53
_journal_year                    2024
_chemical_formula_moiety         '1(C11 H25 Cd N7), 2(Cl O4)'
_chemical_formula_sum            'C11 H25 Cd Cl2 N7 O8'
_chemical_formula_weight         566.68
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2022-03-20
_audit_creation_method
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2023-04-17 deposited with the CCDC.	2023-12-07 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.42(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   7.9100(16)
_cell_length_b                   34.610(7)
_cell_length_c                   14.770(3)
_cell_measurement_reflns_used    1122
_cell_measurement_temperature    100.0(2)
_cell_measurement_theta_max      22.61
_cell_measurement_theta_min      2.23
_cell_volume                     4031.5(14)
_computing_cell_refinement       'XDS (Kabsch, 2010)'
_computing_data_collection       'AS QEGUI'
_computing_data_reduction        'XDS (Kabsch, 2010)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      100.0(2)
_diffrn_detector_area_resol_mean 13.3
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.901
_diffrn_measurement_device_type  'MX1 Beamline Australian Synchrotron'
_diffrn_measurement_method       'Omega Scan'
_diffrn_radiation_monochromator  'Silicon Double Crystal'
_diffrn_radiation_type           Synchrotron
_diffrn_radiation_wavelength     0.71076
_diffrn_reflns_av_R_equivalents  0.0663
_diffrn_reflns_av_unetI/netI     0.0293
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.901
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       45
_diffrn_reflns_limit_k_min       -46
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            102521
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.901
_diffrn_reflns_theta_full        25.243
_diffrn_reflns_theta_max         28.587
_diffrn_reflns_theta_min         1.177
_diffrn_source                   'MX1 Beamline Australian Synchrotron'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.404
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6798
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'XDS (Kabsch, 2010)'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.867
_exptl_crystal_description       needle
_exptl_crystal_F_000             2288
_exptl_crystal_recrystallization_method
'grown by slow evaporation from methanol/ethanol/acetonitrile'
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.824
_refine_diff_density_min         -0.695
_refine_diff_density_rms         0.094
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     922
_refine_ls_number_reflns         9289
_refine_ls_number_restraints     612
_refine_ls_restrained_S_all      1.114
_refine_ls_R_factor_all          0.0476
_refine_ls_R_factor_gt           0.0402
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0555P)^2^+5.6686P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1009
_refine_ls_wR_factor_ref         0.1074
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7914
_reflns_number_total             9289
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3dt03281g2.cif
_cod_data_source_block           rwg2022_ph104_108m
_cod_depositor_comments
'Adding full bibliography for 7714716--7714722.cif.'
_cod_database_code               7714722
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.933
_shelx_estimated_absorpt_t_min   0.767
_exptl_absorpt_special_details
;
XDS does not report the values of _exptl_absorpt_correction_T_min and
_exptl_absorpt_correction_T_max.  Even though the data was processed by XDS
the values of the absorption corrections reported by SADABS (Bruker, 2001) are
reported.
;
_diffrn_measurement_detector_type 'Dectris Eiger2 9M'
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H,H) groups, All N(H,H) groups
2. Restrained distances
 Cl1-O1 = Cl1-O2 = Cl1-O3 = Cl1-O4
 1.42 with sigma of 0.001
 O1-O2 = O1-O3 = O1-O4 = O2-O3 = O2-O4 = O3-O4
 2.31986 with sigma of 0.001
 Cl1A-O1A = Cl1A-O2A = Cl1A-O3A = Cl1A-O4A
 1.42 with sigma of 0.001
 O1A-O2A = O1A-O3A = O1A-O4A = O2A-O3A = O2A-O4A = O3A-O4A
 2.31986 with sigma of 0.001
 Cl1B-O1B = Cl1B-O2B = Cl1B-O3B = Cl1B-O4B
 1.42 with sigma of 0.001
 O1B-O2B = O1B-O3B = O1B-O4B = O2B-O3B = O2B-O4B = O3B-O4B
 2.31986 with sigma of 0.001
 Cl3-O9 = Cl3-O10 = Cl3-O11 = Cl3-O12
 1.42 with sigma of 0.001
 O9-O10 = O9-O11 = O9-O12 = O10-O11 = O10-O12 = O11-O12
 2.31986 with sigma of 0.001
 Cl3A-O9A = Cl3A-O10A = Cl3A-O11A = Cl3A-O12A
 1.42 with sigma of 0.001
 O9A-O10A = O9A-O11A = O9A-O12A = O10A-O11A = O10A-O12A = O11A-O12A
 2.31986 with sigma of 0.001
 Cl3B-O9B = Cl3B-O10B = Cl3B-O11B = Cl3B-O12B
 1.42 with sigma of 0.001
 O9B-O10B = O9B-O11B = O9B-O12B = O10B-O11B = O10B-O12B = O11B-O12B
 2.31986 with sigma of 0.001
 Cl4-O13 = Cl4-O14 = Cl4-O15 = Cl4-O16
 1.42 with sigma of 0.001
 O13-O14 = O13-O15 = O13-O16 = O14-O15 = O14-O16 = O15-O16
 2.31986 with sigma of 0.001
 Cl4A-O13A = Cl4A-O14A = Cl4A-O15A = Cl4A-O16A
 1.42 with sigma of 0.001
 O13A-O14A = O13A-O15A = O13A-O16A = O14A-O15A = O14A-O16A = O15A-O16A
 2.31986 with sigma of 0.001
 N6-H6A = N6-H6B = N7-H7A = N7-H7B
 0.88 with sigma of 0.005
 H6A-H6B = H7A-H7B
 1.41 with sigma of 0.005
 N13-H13A = N13-H13B = N14-H14A = N14-H14B
 0.88 with sigma of 0.005
 H13A-H13B = H14A-H14B
 1.41 with sigma of 0.005
 N13A-H13E = N13A-H13F = N14A-H14E = N14A-H14F
 0.88 with sigma of 0.005
 H13E-H13F = H14E-H14F
 1.41 with sigma of 0.005
 N13B-H13I = N13B-H13J = N14B-H14I = N14B-H14J
 0.88 with sigma of 0.005
 H13I-H13J = H14I-H14J
 1.41 with sigma of 0.005
 C20-H13A = C20-H13B = C21-H14A = C21-H14B
 1.92827 with sigma of 0.005
 C20A-H13E = C20A-H13F = C21A-H14E = C21A-H14F
 1.92827 with sigma of 0.005
 C20B-H13I = C20A-H13J = C21B-H14I = C21A-H14J
 1.92827 with sigma of 0.005
3. Uiso/Uaniso restraints and constraints
Cl1 \\sim Cl1A \\sim Cl1B: within 2A with sigma of 0.001 and sigma for terminal
atoms of 0.002 within 2A
O1 \\sim O2 \\sim O3 \\sim O4 \\sim O1A \\sim O2A \\sim O3A \\sim O4A \\sim O1B
\\sim O2B \\sim O3B \\sim O4B: within 2A with sigma of 0.001 and sigma for
terminal atoms of 0.002 within 2A
Cl3 \\sim Cl3A \\sim Cl3B: within 2A with sigma of 0.001 and sigma for terminal
atoms of 0.002 within 2A
O9 \\sim O10 \\sim O11 \\sim O12 \\sim O9A \\sim O10A \\sim O11A \\sim O12A
\\sim O9B \\sim O10B \\sim O11B \\sim O12B: within 2A with sigma of 0.001 and
sigma for terminal atoms of 0.002 within 2A
Cl4 \\sim Cl4A: within 2A with sigma of 0.001 and sigma for terminal atoms of
0.002 within 2A
O13 \\sim O14 \\sim O15 \\sim O16 \\sim O13A \\sim O14A \\sim O15A \\sim O16A:
within 2A with sigma of 0.001 and sigma for terminal atoms of 0.002 within 2A
Uanis(C20) \\sim Ueq: with sigma of 0.007 and sigma for terminal atoms of 0.014
Uanis(Cd2) = Uanis(Cd2A) = Uanis(Cd2B)
Uanis(N8) = Uanis(N8A) = Uanis(N8B)
Uanis(N9) = Uanis(N9A) = Uanis(N9B)
Uanis(N10) = Uanis(N10A) = Uanis(N10B)
Uanis(N11) = Uanis(N11A) = Uanis(N11B)
Uanis(N12) = Uanis(N12A) = Uanis(N12B)
Uanis(N13) = Uanis(N13A) = Uanis(N13B)
Uanis(N14) = Uanis(N14A) = Uanis(N14B)
Uanis(C12) = Uanis(C12A) = Uanis(C12B)
Uanis(C13) = Uanis(C13A) = Uanis(C13B)
Uanis(C14) = Uanis(C14A) = Uanis(C14B)
Uanis(C15) = Uanis(C15A) = Uanis(C15B)
Uanis(C16) = Uanis(C16A) = Uanis(C16B)
Uanis(C17) = Uanis(C17A) = Uanis(C17B)
Uanis(C18) = Uanis(C18A) = Uanis(C18B)
Uanis(C19) = Uanis(C19A) = Uanis(C19B)
Uanis(C20) = Uanis(C20A) = Uanis(C20B)
Uanis(C21) = Uanis(C21A) = Uanis(C21B)
Uanis(C22) = Uanis(C22A) = Uanis(C22B)
4. Same fragment restrains
{Cd2, N8, N9, N10, N11, N12, N13, N14, C12, C13, C14, C15, C16, C17, C18, C19,
C20, C21, C22} sigma for 1-2: 0.01, 1-3: 0.02
as in
{Cd2A, N8A, N9A, N10A, N11A, N12A, N13A, N14A, C12A, C13A, C14A, C15A, C16A,
C17A, C18A, C19A, C20A, C21A, C22A}
{Cd2, N8, N9, N10, N11, N12, N13, N14, C12, C13, C14, C15, C16, C17, C18, C19,
C20, C21, C22} sigma for 1-2: 0.01, 1-3: 0.02
as in
{Cd2B, N8B, N9B, N10B, N11B, N12B, N13B, N14B, C12B, C13B, C14B, C15B, C16B,
C17B, C18B, C19B, C20B, C21B, C22B}
5. Others
 1*[Sof(Cd2)+Sof(N8)+Sof(N9)+Sof(H9A)+Sof(H9B)+Sof(N10)+Sof(H10A)+Sof(H10B)+
 Sof(N11)+Sof(H11A)+Sof(H11B)+Sof(N12)+Sof(N13)+Sof(N14)+Sof(C12)+Sof(H12A)+
 Sof(H12B)+Sof(C13)+Sof(H13C)+Sof(H13D)+Sof(C14)+Sof(H14C)+Sof(H14D)+Sof(C15)+
 Sof(H15A)+Sof(H15B)+Sof(C16)+Sof(H16A)+Sof(H16B)+Sof(C17)+Sof(H17A)+Sof(H17B)+
 Sof(C18)+Sof(H18)+Sof(C19)+Sof(H19)+Sof(C20)+Sof(C21)+Sof(C22)+Sof(H22)+
 Sof(H13A)+Sof(H13B)+Sof(H14A)+Sof(H14B)]+1*[Sof(Cd2A)+Sof(N8A)+Sof(N9A)+
 Sof(H9AA)+Sof(H9AB)+Sof(N10A)+Sof(H10C)+Sof(H10D)+Sof(N11A)+Sof(H11C)+
 Sof(H11D)+Sof(N12A)+Sof(N13A)+Sof(N14A)+Sof(C12A)+Sof(H12C)+Sof(H12D)+
 Sof(C13A)+Sof(H13G)+Sof(H13H)+Sof(C14A)+Sof(H14G)+Sof(H14H)+Sof(C15A)+
 Sof(H15C)+Sof(H15D)+Sof(C16A)+Sof(H16C)+Sof(H16D)+Sof(C17A)+Sof(H17C)+
 Sof(H17D)+Sof(C18A)+Sof(H18A)+Sof(C19A)+Sof(H19A)+Sof(C20A)+Sof(C21A)+
 Sof(C22A)+Sof(H22A)+Sof(H13E)+Sof(H13F)+Sof(H14E)+Sof(H14F)]+1*[Sof(Cd2B)+
 Sof(N8B)+Sof(N9B)+Sof(H9BA)+Sof(H9BB)+Sof(N10B)+Sof(H10E)+Sof(H10F)+Sof(N11B)+
 Sof(H11E)+Sof(H11F)+Sof(N12B)+Sof(N13B)+Sof(N14B)+Sof(C12B)+Sof(H12E)+
 Sof(H12F)+Sof(C13B)+Sof(H13K)+Sof(H13L)+Sof(C14B)+Sof(H14K)+Sof(H14L)+
 Sof(C15B)+Sof(H15E)+Sof(H15F)+Sof(C16B)+Sof(H16E)+Sof(H16F)+Sof(C17B)+
 Sof(H17E)+Sof(H17F)+Sof(C18B)+Sof(H18B)+Sof(C19B)+Sof(H19B)+Sof(C20B)+
 Sof(C21B)+Sof(C22B)+Sof(H22B)+Sof(H13I)+Sof(H13J)+Sof(H14I)+Sof(H14J)]=1 with
 esd of 0.00001
 1*[Sof(Cl1)+Sof(O1)+Sof(O2)+Sof(O3)+Sof(O4)]+1*[Sof(Cl1A)+Sof(O1A)+Sof(O2A)+
 Sof(O3A)+Sof(O4A)]+1*[Sof(Cl1B)+Sof(O1B)+Sof(O2B)+Sof(O3B)+Sof(O4B)]=1 with
 esd of 0.00001
 1*[Sof(Cl3)+Sof(O9)+Sof(O10)+Sof(O11)+Sof(O12)]+1*[Sof(Cl3A)+Sof(O9A)+
 Sof(O10A)+Sof(O11A)+Sof(O12A)]+1*[Sof(Cl3B)+Sof(O9B)+Sof(O10B)+Sof(O11B)+
 Sof(O12B)]=1 with esd of 0.00001
 Sof(Cd2)=Sof(N8)=Sof(N9)=Sof(H9A)=Sof(H9B)=Sof(N10)=Sof(H10A)=Sof(H10B)=
 Sof(N11)=Sof(H11A)=Sof(H11B)=Sof(N12)=Sof(N13)=Sof(N14)=Sof(C12)=Sof(H12A)=
 Sof(H12B)=Sof(C13)=Sof(H13C)=Sof(H13D)=Sof(C14)=Sof(H14C)=Sof(H14D)=Sof(C15)=
 Sof(H15A)=Sof(H15B)=Sof(C16)=Sof(H16A)=Sof(H16B)=Sof(C17)=Sof(H17A)=Sof(H17B)=
 Sof(C18)=Sof(H18)=Sof(C19)=Sof(H19)=Sof(C20)=Sof(C21)=Sof(C22)=Sof(H22)=
 Sof(H13A)=Sof(H13B)=Sof(H14A)=Sof(H14B)=FVAR(1)
 Sof(Cl3)=Sof(O9)=Sof(O10)=Sof(O11)=Sof(O12)=FVAR(2)
 1(DFIX)=1(DFIX)=1(DFIX)=1(DFIX)=1(DFIX)=1(DFIX)=1(DFIX)=1(DFIX)=FVAR(3)
 Sof(Cl1)=Sof(O1)=Sof(O2)=Sof(O3)=Sof(O4)=FVAR(4)
 Sof(Cd2A)=Sof(N8A)=Sof(N9A)=Sof(H9AA)=Sof(H9AB)=Sof(N10A)=Sof(H10C)=Sof(H10D)=
 Sof(N11A)=Sof(H11C)=Sof(H11D)=Sof(N12A)=Sof(N13A)=Sof(N14A)=Sof(C12A)=
 Sof(H12C)=Sof(H12D)=Sof(C13A)=Sof(H13G)=Sof(H13H)=Sof(C14A)=Sof(H14G)=
 Sof(H14H)=Sof(C15A)=Sof(H15C)=Sof(H15D)=Sof(C16A)=Sof(H16C)=Sof(H16D)=
 Sof(C17A)=Sof(H17C)=Sof(H17D)=Sof(C18A)=Sof(H18A)=Sof(C19A)=Sof(H19A)=
 Sof(C20A)=Sof(C21A)=Sof(C22A)=Sof(H22A)=Sof(H13E)=Sof(H13F)=Sof(H14E)=
 Sof(H14F)=FVAR(5)
 Sof(Cd2B)=Sof(N8B)=Sof(N9B)=Sof(H9BA)=Sof(H9BB)=Sof(N10B)=Sof(H10E)=Sof(H10F)=
 Sof(N11B)=Sof(H11E)=Sof(H11F)=Sof(N12B)=Sof(N13B)=Sof(N14B)=Sof(C12B)=
 Sof(H12E)=Sof(H12F)=Sof(C13B)=Sof(H13K)=Sof(H13L)=Sof(C14B)=Sof(H14K)=
 Sof(H14L)=Sof(C15B)=Sof(H15E)=Sof(H15F)=Sof(C16B)=Sof(H16E)=Sof(H16F)=
 Sof(C17B)=Sof(H17E)=Sof(H17F)=Sof(C18B)=Sof(H18B)=Sof(C19B)=Sof(H19B)=
 Sof(C20B)=Sof(C21B)=Sof(C22B)=Sof(H22B)=Sof(H13I)=Sof(H13J)=Sof(H14I)=
 Sof(H14J)=FVAR(6)
 1(DFIX)=1(DFIX)=1(DFIX)=FVAR(7)
 Sof(Cl1A)=Sof(O1A)=Sof(O2A)=Sof(O3A)=Sof(O4A)=FVAR(8)
 Sof(Cl1B)=Sof(O1B)=Sof(O2B)=Sof(O3B)=Sof(O4B)=FVAR(9)
 Sof(Cl3A)=Sof(O9A)=Sof(O10A)=Sof(O11A)=Sof(O12A)=FVAR(10)
 Sof(Cl3B)=Sof(O9B)=Sof(O10B)=Sof(O11B)=Sof(O12B)=FVAR(11)
 Sof(Cl4A)=Sof(O13A)=Sof(O14A)=Sof(O15A)=Sof(O16A)=1-FVAR(12)
 Sof(Cl4)=Sof(O13)=Sof(O14)=Sof(O15)=Sof(O16)=FVAR(12)
6.a Secondary CH2 refined with riding coordinates:
 N2(H2A,H2B), N3(H3A,H3B), N4(H4A,H4B), C1(H1A,H1B), C2(H2C,H2D), C3(H3C,H3D),
 C4(H4C,H4D), C5(H5A,H5B), C6(H6C,H6D), N9(H9A,H9B), N10(H10A,H10B), N11(H11A,
 H11B), C12(H12A,H12B), C13(H13C,H13D), C14(H14C,H14D), C15(H15A,H15B),
 C16(H16A,H16B), C17(H17A,H17B), N9A(H9AA,H9AB), N10A(H10C,H10D), N11A(H11C,
 H11D), C12A(H12C,H12D), C13A(H13G,H13H), C14A(H14G,H14H), C15A(H15C,H15D),
 C16A(H16C,H16D), C17A(H17C,H17D), N9B(H9BA,H9BB), N10B(H10E,H10F), N11B(H11E,
 H11F), C12B(H12E,H12F), C13B(H13K,H13L), C14B(H14K,H14L), C15B(H15E,H15F),
 C16B(H16E,H16F), C17B(H17E,H17F)
6.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C11(H11), C18(H18), C19(H19), C22(H22), C18A(H18A),
 C19A(H19A), C22A(H22A), C18B(H18B), C19B(H19B), C22B(H22B)
;
_shelx_res_checksum              73912
_olex2_exptl_crystal_mounting_method mounted
_olex2_submission_special_instructions 'No special instructions were received'