# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2021

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_Me-Malten
_database_code_depnum_ccdc_archive 'CCDC 2040416'
loop_
_audit_author_name
_audit_author_address
'Patrizia Rossi'
;University of Firenze
Italy
;
_audit_update_record             
;
2020-12-19 deposited with the CCDC.	2020-12-30 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT910_Me-Malten           
;
PROBLEM: Missing # of FCF Reflection(s) Below Theta(Min). 12 Note
RESPONSE: the missing of these few low angle
reflections is probably missing due to the beamstop
;
# end Validation Reply Form

_publ_section_title_             
;
Bis-maltol-polyamine Family: Structural Modifications at Strategic 
Positions. Synthesis, Coordination and Antineoplastic Activity 
of Two New Ligands
;


_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '(C18 H26 O6 N2) 2(H2O) 2(ClO4-))'
_chemical_formula_sum            'C18 H30 Cl2 N2 O16'
_chemical_formula_weight         601.34


loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.0335(7)
_cell_length_b                   8.3743(8)
_cell_length_c                   10.4076(10)
_cell_angle_alpha                104.296(9)
_cell_angle_beta                 104.670(8)
_cell_angle_gamma                105.419(8)
_cell_volume                     614.77(11)
_cell_formula_units_Z            1
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3301
_cell_measurement_theta_min      4.7600
_cell_measurement_theta_max      29.1830


_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.624
_exptl_crystal_F_000             314
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.18
_exptl_absorpt_coefficient_mu    0.348
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.97714
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41r (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            2905
_diffrn_reflns_av_unetI/netI     0.0434
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         4.255
_diffrn_reflns_theta_max         29.532
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.847
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.847
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.847
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             2905
_reflns_number_gt                2491
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;

_computing_data_collection       'CrysAlisPro 1.171.38.41r (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41r (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41r (Rigaku OD, 2015)'
_computing_structure_solution    'SIR-2004 (Burla, 2005)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Mercury (Macrae, 2008)'
_computing_publication_material  'Parst-97 (Nardelli, 1995)'
_refine_special_details          
;
 Refined as a 2-component twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0452P)²+0.8705P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2905
_refine_ls_number_parameters     218
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0606
_refine_ls_R_factor_gt           0.0505
_refine_ls_wR_factor_ref         0.1371
_refine_ls_wR_factor_gt          0.1325
_refine_ls_goodness_of_fit_ref   1.188
_refine_ls_restrained_S_all      1.188
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.9249(3) 0.2157(3) 0.5864(2) 0.0141(4) Uani 1 1 d . . . . .
H1O H 1.005(5) 0.192(5) 0.610(4) 0.017 Uiso 1 1 d . U . . .
O2 O 1.2052(3) 0.2268(3) 0.4807(2) 0.0157(4) Uani 1 1 d . . . . .
O3 O 0.7734(3) 0.3452(2) 0.2861(2) 0.0122(4) Uani 1 1 d . . . . .
N1 N 0.4576(3) 0.1368(3) 0.3818(2) 0.0102(5) Uani 1 1 d . . . . .
H1N H 0.376(5) 0.165(4) 0.417(3) 0.012 Uiso 1 1 d . U . . .
C1 C 0.9085(4) 0.3477(3) 0.2314(3) 0.0134(6) Uani 1 1 d . . . . .
C2 C 1.0560(4) 0.3103(4) 0.2932(3) 0.0129(5) Uani 1 1 d . . . . .
H2 H 1.143(5) 0.317(4) 0.258(4) 0.015 Uiso 1 1 d . U . . .
C3 C 1.0733(4) 0.2637(3) 0.4164(3) 0.0119(5) Uani 1 1 d . . . . .
C4 C 0.9222(4) 0.2588(3) 0.4700(3) 0.0108(5) Uani 1 1 d . . . . .
C5 C 0.7805(4) 0.2998(3) 0.4040(3) 0.0101(5) Uani 1 1 d . . . . .
C6 C 0.6201(4) 0.3060(3) 0.4495(3) 0.0110(5) Uani 1 1 d . . . . .
H6A H 0.653(4) 0.338(4) 0.547(4) 0.013 Uiso 1 1 d . U . . .
H6B H 0.577(4) 0.392(4) 0.424(3) 0.013 Uiso 1 1 d . U . . .
C7 C 0.4898(4) -0.0141(4) 0.4232(3) 0.0118(5) Uani 1 1 d . . . . .
H7A H 0.382(5) -0.114(4) 0.366(4) 0.014 Uiso 1 1 d . U . . .
H7B H 0.596(5) -0.025(4) 0.407(3) 0.014 Uiso 1 1 d . U . . .
C15 C 0.3892(4) 0.0863(4) 0.2241(3) 0.0150(6) Uani 1 1 d . . . . .
H15A H 0.382(5) 0.191(5) 0.204(4) 0.022 Uiso 1 1 d . U . . .
H15B H 0.474(5) 0.041(5) 0.194(4) 0.022 Uiso 1 1 d . U . . .
H15C H 0.274(5) 0.004(5) 0.202(4) 0.022 Uiso 1 1 d . U . . .
C16 C 0.8730(5) 0.3927(5) 0.1006(4) 0.0203(6) Uani 1 1 d . . . . .
H16A H 0.950(5) 0.365(5) 0.043(4) 0.030 Uiso 1 1 d . U . . .
H16B H 0.750(6) 0.321(5) 0.034(4) 0.030 Uiso 1 1 d . U . . .
H16C H 0.890(5) 0.502(6) 0.118(4) 0.030 Uiso 1 1 d . U . . .
O1W O 1.5450(3) 0.4433(3) 0.7414(3) 0.0224(5) Uani 1 1 d . . . . .
H1WA H 1.577(6) 0.496(5) 0.835(5) 0.034 Uiso 1 1 d . U . . .
H1WB H 1.452(6) 0.378(6) 0.720(5) 0.034 Uiso 1 1 d . U . . .
Cl1 Cl 1.23754(9) 0.15992(8) 0.88243(7) 0.01202(18) Uani 1 1 d . . . . .
O11 O 1.2163(3) 0.1424(3) 0.7358(2) 0.0187(5) Uani 1 1 d . . . . .
O12 O 1.3679(4) 0.3317(3) 0.9691(3) 0.0306(6) Uani 1 1 d . . . . .
O13 O 1.3052(3) 0.0285(3) 0.9158(2) 0.0213(5) Uani 1 1 d . . . . .
O14 O 1.0649(3) 0.1400(4) 0.9012(3) 0.0321(6) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C4 1.344(3) . ?
O1 H1O 0.72(4) . ?
O2 C3 1.258(3) . ?
O3 C1 1.345(3) . ?
O3 C5 1.364(3) . ?
N1 C7 1.495(3) . ?
N1 C15 1.501(4) . ?
N1 C6 1.505(3) . ?
N1 H1N 0.88(3) . ?
C1 C2 1.351(4) . ?
C1 C16 1.480(4) . ?
C2 C3 1.415(4) . ?
C2 H2 0.87(3) . ?
C3 C4 1.454(4) . ?
C4 C5 1.347(4) . ?
C5 C6 1.490(4) . ?
C6 H6A 0.93(3) . ?
C6 H6B 0.94(3) . ?
C7 C7 1.517(5) 2_656 ?
C7 H7A 0.95(3) . ?
C7 H7B 0.94(3) . ?
C15 H15A 0.96(4) . ?
C15 H15B 0.94(4) . ?
C15 H15C 0.92(4) . ?
C16 H16A 1.00(4) . ?
C16 H16B 0.97(4) . ?
C16 H16C 0.85(4) . ?
O1W H1WA 0.90(5) . ?
O1W H1WB 0.74(5) . ?
Cl1 O14 1.421(2) . ?
Cl1 O13 1.428(2) . ?
Cl1 O12 1.435(2) . ?
Cl1 O11 1.457(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C4 O1 H1O 110(3) . . ?
C1 O3 C5 120.3(2) . . ?
C7 N1 C15 110.1(2) . . ?
C7 N1 C6 114.3(2) . . ?
C15 N1 C6 111.6(2) . . ?
C7 N1 H1N 108(2) . . ?
C15 N1 H1N 110(2) . . ?
C6 N1 H1N 102(2) . . ?
O3 C1 C2 121.3(2) . . ?
O3 C1 C16 112.4(2) . . ?
C2 C1 C16 126.3(3) . . ?
C1 C2 C3 121.5(2) . . ?
C1 C2 H2 119(2) . . ?
C3 C2 H2 119(2) . . ?
O2 C3 C2 125.9(2) . . ?
O2 C3 C4 118.9(2) . . ?
C2 C3 C4 115.3(2) . . ?
O1 C4 C5 119.9(2) . . ?
O1 C4 C3 120.1(2) . . ?
C5 C4 C3 120.0(2) . . ?
C4 C5 O3 121.6(2) . . ?
C4 C5 C6 125.8(2) . . ?
O3 C5 C6 112.5(2) . . ?
C5 C6 N1 113.9(2) . . ?
C5 C6 H6A 111(2) . . ?
N1 C6 H6A 109(2) . . ?
C5 C6 H6B 110.1(19) . . ?
N1 C6 H6B 105(2) . . ?
H6A C6 H6B 107(3) . . ?
N1 C7 C7 111.3(3) . 2_656 ?
N1 C7 H7A 105(2) . . ?
C7 C7 H7A 108(2) 2_656 . ?
N1 C7 H7B 108(2) . . ?
C7 C7 H7B 110(2) 2_656 . ?
H7A C7 H7B 113(3) . . ?
N1 C15 H15A 106(2) . . ?
N1 C15 H15B 105(2) . . ?
H15A C15 H15B 116(3) . . ?
N1 C15 H15C 101(2) . . ?
H15A C15 H15C 112(3) . . ?
H15B C15 H15C 115(3) . . ?
C1 C16 H16A 115(2) . . ?
C1 C16 H16B 112(2) . . ?
H16A C16 H16B 101(3) . . ?
C1 C16 H16C 112(3) . . ?
H16A C16 H16C 107(3) . . ?
H16B C16 H16C 110(3) . . ?
H1WA O1W H1WB 105(4) . . ?
O14 Cl1 O13 110.80(14) . . ?
O14 Cl1 O12 110.28(16) . . ?
O13 Cl1 O12 109.85(15) . . ?
O14 Cl1 O11 109.24(14) . . ?
O13 Cl1 O11 108.72(12) . . ?
O12 Cl1 O11 107.87(14) . . ?

_refine_diff_density_max         0.515
_refine_diff_density_min         -0.418
_refine_diff_density_rms         0.087



