Water soluble Ru(ii)‒arene complexes of the antidiabetic drug metformin: DNA and protein binding, molecular docking, cytotoxicity and apoptosis-inducing activity
Gopalakrishnan, Durairaj; Ganeshpandian, Mani; Loganathan, Rangasamy; Bhuvanesh, Nattamai S. P.; Sabina, Xavier Janet; Karthikeyan, J.; RSC Adv. 7 (2017) 37706–; doi:10.1039/C7RA06514K

data_7228818
_publ_section_title
;
 Water soluble Ru(ii)--arene complexes of the antidiabetic drug metformin:
 DNA and protein binding, molecular docking, cytotoxicity and
 apoptosis-inducing activity
;
_journal_issue                   60
_journal_name_full               'RSC Adv.'
_journal_page_first              37706
_journal_paper_doi               10.1039/C7RA06514K
_journal_volume                  7
_journal_year                    2017
_chemical_formula_moiety
'0.5(C14 H25 Cl N5 Ru), 0.5(C14 H25 N5 Ru), 1.5(Cl), H2 O'
_chemical_formula_sum            'C14 H27 Cl2 N5 O Ru'
_chemical_formula_weight         453.37
_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'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2017-04-28
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_audit_update_record
;
2017-05-02 deposited with the CCDC.
2017-07-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 111.576(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   16.876(4)
_cell_length_b                   12.155(3)
_cell_length_c                   19.495(4)
_cell_measurement_reflns_used    9942
_cell_measurement_temperature    110.0
_cell_measurement_theta_max      27.420
_cell_measurement_theta_min      2.595
_cell_volume                     3718.8(15)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      110.0
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0571
_diffrn_reflns_av_unetI/netI     0.0500
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            41081
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.495
_diffrn_reflns_theta_min         1.369
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.141
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5164
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/3 (Bruker,2014/3) was used for absorption correction.
wR2(int) was 0.1195 before and 0.0591 after correction.
The Ratio of minimum to maximum transmission is 0.6926.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            brown
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.620
_exptl_crystal_description       block
_exptl_crystal_F_000             1856
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.464
_exptl_crystal_size_min          0.254
_refine_diff_density_max         0.559
_refine_diff_density_min         -0.559
_refine_diff_density_rms         0.110
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     519
_refine_ls_number_reflns         8480
_refine_ls_number_restraints     478
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.0611
_refine_ls_R_factor_gt           0.0416
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0174P)^2^+6.5707P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0699
_refine_ls_wR_factor_ref         0.0767
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6714
_reflns_number_total             8480
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7ra06514k2.cif
_cod_data_source_block           gp1
_cod_original_cell_volume        3718.6(14)
_cod_database_code               7228818
_shelx_shelxl_version_number     2014/7
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, H2 of N2, H7 of N7
 At 1.5 times of:
  All C(H,H,H) groups, H1 of N1, H3 of N3, H6 of N6, H8 of N8, All N(H,H)
  groups, All O(H,H) groups
2. Restrained distances
 C26A-C25A = C26-C25 = C27A-C25A = C27-C25
 1.54 with sigma of 0.02
 C26A-C25A \\sim C27A-C25A \\sim C27-C25 \\sim C26-C25
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
C19 \\sim C20 \\sim C21 \\sim C22 \\sim C23 \\sim C24 \\sim C25 \\sim C26 \\sim
C27 \\sim C28 \\sim C19A \\sim C20A \\sim C21A \\sim C22A \\sim C23A \\sim C24A
\\sim C25A \\sim C26A \\sim C27A \\sim C28A: within 2A with sigma of 0.04 and
sigma for terminal atoms of 0.08
4. Rigid body (RIGU) restrains
 C19, C20, C21, C22, C23, C24, C25, C26, C27, C28, C19A, C20A, C21A, C22A,
 C23A, C24A, C25A, C26A, C27A, C28A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Same fragment restrains
{C19, C20, C21, C22, C23, C24, C25, C26, C27, C28} sigma for 1-2: 0.02, 1-3:
0.04
as
{C19A, C20A, C21A, C22A, C23A, C24A, C25A, C26A, C27A, C28A}
6. Others
 Sof(C19A)=Sof(C20A)=Sof(H20A)=Sof(C21A)=Sof(H21A)=Sof(C22A)=Sof(C23A)=
 Sof(H23A)=Sof(C24A)=Sof(H24A)=Sof(C25A)=Sof(H25A)=Sof(C26A)=Sof(H26D)=
 Sof(H26E)=Sof(H26F)=Sof(C27A)=Sof(H27D)=Sof(H27E)=Sof(H27F)=Sof(C28A)=
 Sof(H28D)=Sof(H28E)=Sof(H28F)=1-FVAR(1)
 Sof(C19)=Sof(C20)=Sof(H20)=Sof(C21)=Sof(H21)=Sof(C22)=Sof(C23)=Sof(H23)=
 Sof(C24)=Sof(H24)=Sof(C25)=Sof(H25)=Sof(C26)=Sof(H26A)=Sof(H26B)=Sof(H26C)=
 Sof(C27)=Sof(H27A)=Sof(H27B)=Sof(H27C)=Sof(C28)=Sof(H28A)=Sof(H28B)=Sof(H28C)=
 FVAR(1)
7.a Riding coordinates:
 N1(H1), N3(H3), N5(H5A,H5B), N6(H6), N8(H8), N10(H10A,H10B), O2(H2A,H2B),
 O1(H1A,H1B)
7.b Ternary CH refined with riding coordinates:
 C11(H11), C25(H25), C25A(H25A)
7.c Aromatic/amide H refined with riding coordinates:
 N2(H2), C6(H6A), C7(H7A), C9(H9), C10(H10), N7(H7), C20(H20), C21(H21),
 C23(H23), C24(H24), C20A(H20A), C21A(H21A), C23A(H23A), C24A(H24A)
7.d Idealised Me refined as rotating group:
 C3(H3A,H3B,H3C), C4(H4A,H4B,H4C), C12(H12A,H12B,H12C), C13(H13A,H13B,H13C),
 C14(H14A,H14B,H14C), C17(H17A,H17B,H17C), C18(H18A,H18B,H18C), C26(H26A,H26B,
 H26C), C27(H27A,H27B,H27C), C28(H28A,H28B,H28C), C26A(H26D,H26E,H26F),
 C27A(H27D,H27E,H27F), C28A(H28D,H28E,H28F)
;
_shelx_res_checksum              90304
_olex2_submission_special_instructions 'No special instructions were received'