#------------------------------------------------------------------------------
#$Date: 2025-08-21 23:13:44 +0200 (Thu 21 de Aug de 2025) $
#$Revision: 301852 $
#$URL: svn://www.crystallography.net/cod/cif/7/06/02/7060224.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7060224
loop_
_publ_author_name
'Giorgi, Luca'
'Ambrosi, Gianluca'
'Paderni, Daniele'
'Conti, Luca'
'Amatori, Stefano'
'Romagnoli, Francesca'
'Rossi, Patrizia'
'Formica, Mauro'
'Macedi, Eleonora'
'Giorgi, Claudia'
'Paoli, Paola'
'Fanelli, Mirco'
'Fusi, Vieri'
_publ_section_title
;
 Bis-maltol-polyamine family: structural modifications at strategic
 positions. Synthesis, coordination and antineoplastic activity of two new
 ligands
;
_journal_issue                   5
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              2659
_journal_page_last               2669
_journal_paper_doi               10.1039/D0NJ05327A
_journal_volume                  45
_journal_year                    2021
_chemical_formula_moiety         '(C18 H26 O6 N2) 2(H2O) 2(ClO4-))'
_chemical_formula_sum            'C18 H30 Cl2 N2 O16'
_chemical_formula_weight         601.34
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   difmap
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2020-12-19 deposited with the CCDC.	2020-12-30 downloaded from the CCDC.
;
_cell_angle_alpha                104.296(9)
_cell_angle_beta                 104.670(8)
_cell_angle_gamma                105.419(8)
_cell_formula_units_Z            1
_cell_length_a                   8.0335(7)
_cell_length_b                   8.3743(8)
_cell_length_c                   10.4076(10)
_cell_measurement_reflns_used    3301
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.1830
_cell_measurement_theta_min      4.7600
_cell_volume                     614.77(12)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41r (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41r (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41r (Rigaku OD, 2015)'
_computing_molecular_graphics    'Mercury (Macrae, 2008)'
_computing_publication_material  'Parst-97 (Nardelli, 1995)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SIR-2004 (Burla, 2005)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.847
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_unetI/netI     0.0434
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.847
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            2905
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.847
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.532
_diffrn_reflns_theta_min         4.255
_diffrn_source                   'fine-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.348
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.97714
_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_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.624
_exptl_crystal_description       prism
_exptl_crystal_F_000             314
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.515
_refine_diff_density_min         -0.418
_refine_diff_density_rms         0.087
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.188
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         2905
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.188
_refine_ls_R_factor_all          0.0606
_refine_ls_R_factor_gt           0.0505
_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/[σ²(Fo²)+(0.0452P)²+0.8705P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1325
_refine_ls_wR_factor_ref         0.1371
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2491
_reflns_number_total             2905
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0nj05327a2.cif
_cod_data_source_block           Me-Malten
_cod_depositor_comments          'Adding full bibliography for 7060224.cif.'
_cod_original_cell_volume        614.77(11)
_cod_database_code               7060224
_shelx_shelxl_version_number     2018/3
_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'
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 . . . . .
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'
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) . . ?
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_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168350036
