#------------------------------------------------------------------------------
#$Date: 2019-10-11 10:57:29 +0300 (Fri, 11 Oct 2019) $
#$Revision: 219282 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/10/60/4106011.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_4106011
loop_
_publ_author_name
'Tardito, Saverio'
'Bassanetti, Irene'
'Bignardi, Chiara'
'Elviri, Lisa'
'Tegoni, Matteo'
'Mucchino, Claudio'
'Bussolati, Ovidio'
'Franchi-Gazzola, Renata'
'Marchiò, Luciano'
_publ_section_title
;
 Copper Binding Agents Acting as Copper Ionophores Lead to Caspase
 Inhibition and Paraptotic Cell Death in Human Cancer Cells
;
_journal_coden_ASTM              JACSAT
_journal_issue                   16
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              6235
_journal_page_last               6242
_journal_paper_doi               10.1021/ja109413c
_journal_volume                  133
_journal_year                    2011
_chemical_formula_moiety         'C28 H38 Cl4 Cu2 N6 O2 S2'
_chemical_formula_sum            'C28 H38 Cl4 Cu2 N6 O2 S2'
_chemical_formula_weight         823.64
_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           SHELXL-97
_cell_angle_alpha                93.069(3)
_cell_angle_beta                 109.670(2)
_cell_angle_gamma                110.080(2)
_cell_formula_units_Z            1
_cell_length_a                   8.576(1)
_cell_length_b                   10.448(2)
_cell_length_c                   11.856(2)
_cell_measurement_reflns_used    9615
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.87
_cell_measurement_theta_min      1.86
_cell_volume                     922.2(3)
_computing_cell_refinement       Saint
_computing_data_collection       Smart
_computing_data_reduction        Saint
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    Sir2004
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker Smart APEXII'
_diffrn_measurement_method       'theta & omega scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0375
_diffrn_reflns_av_sigmaI/netI    0.0483
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            14292
_diffrn_reflns_theta_full        29.87
_diffrn_reflns_theta_max         29.87
_diffrn_reflns_theta_min         1.86
_diffrn_standards_decay_%        none
_exptl_absorpt_coefficient_mu    1.590
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.928
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.483
_exptl_crystal_description       block
_exptl_crystal_F_000             422
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.406
_refine_diff_density_min         -0.378
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     223
_refine_ls_number_reflns         5266
_refine_ls_number_restraints     16
_refine_ls_restrained_S_all      1.004
_refine_ls_R_factor_all          0.0545
_refine_ls_R_factor_gt           0.0357
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0346P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0787
_refine_ls_wR_factor_ref         0.0843
_reflns_number_gt                3801
_reflns_number_total             5266
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja109413c_si_007.cif
_cod_data_source_block           ib142
_cod_depositor_comments
;
 Updated bibliographic information.

 Antanas Vaitkus,
 2019-10-11
;
_cod_database_code               4106011
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu Cu 0.32739(3) 0.47503(3) 0.34519(2) 0.03340(8) Uani 1 1 d . . .
Cl2 Cl 0.45096(7) 0.33114(6) 0.44404(5) 0.04047(13) Uani 1 1 d . . .
S12 S -0.25358(8) 0.18895(6) 0.07317(6) 0.04636(15) Uani 1 1 d . . .
Cl1 Cl 0.47205(9) 0.49388(8) 0.21560(6) 0.05974(18) Uani 1 1 d . . .
N13 N 0.2358(2) 0.62300(17) 0.28032(15) 0.0330(4) Uani 1 1 d . . .
C13 C 0.0623(2) 0.6058(2) 0.22548(17) 0.0308(4) Uani 1 1 d . . .
N11 N -0.0484(2) 0.40724(17) 0.32048(14) 0.0310(4) Uani 1 1 d . . .
C23 C 0.0126(3) 0.7124(2) 0.1833(2) 0.0418(5) Uani 1 1 d . A .
N21 N 0.1067(2) 0.38994(18) 0.38096(15) 0.0350(4) Uani 1 1 d . . .
C43 C 0.3288(3) 0.8641(2) 0.2641(2) 0.0440(5) Uani 1 1 d . A .
C53 C 0.3621(3) 0.7493(2) 0.2968(2) 0.0393(5) Uani 1 1 d . . .
H53 H 0.4814 0.7598 0.3333 0.047 Uiso 1 1 calc R . .
C33 C 0.1484(3) 0.8441(2) 0.2056(2) 0.0502(6) Uani 1 1 d D . .
C11 C 0.0799(3) 0.3260(2) 0.4716(2) 0.0432(5) Uani 1 1 d . . .
H11 H 0.1642 0.3013 0.5288 0.052 Uiso 1 1 calc R . .
C22 C -0.0879(3) 0.3616(2) 0.10359(19) 0.0388(5) Uani 1 1 d . . .
H22A H 0.0286 0.3561 0.1229 0.047 Uiso 1 1 calc R . .
H22B H -0.1138 0.4000 0.0299 0.047 Uiso 1 1 calc R . .
C31 C -0.1695(3) 0.3540(2) 0.3715(2) 0.0381(5) Uani 1 1 d . . .
H31 H -0.2850 0.3531 0.3454 0.046 Uiso 1 1 calc R . .
C12 C -0.0773(2) 0.4616(2) 0.20820(18) 0.0322(4) Uani 1 1 d . . .
H12 H -0.1939 0.4699 0.1844 0.039 Uiso 1 1 calc R . .
C32 C -0.4561(3) 0.2201(3) 0.0057(3) 0.0621(7) Uani 1 1 d . . .
H32A H -0.4748 0.2690 0.0677 0.093 Uiso 1 1 calc R . .
H32B H -0.5560 0.1330 -0.0306 0.093 Uiso 1 1 calc R . .
H32C H -0.4453 0.2749 -0.0558 0.093 Uiso 1 1 calc R . .
C21 C -0.0919(3) 0.3015(2) 0.4683(2) 0.0442(5) Uani 1 1 d . . .
H21 H -0.1431 0.2584 0.5210 0.053 Uiso 1 1 calc R . .
C83 C 0.4824(4) 1.0019(3) 0.2896(3) 0.0754(9) Uani 1 1 d . . .
H83A H 0.4756 1.0345 0.2146 0.113 Uiso 1 1 calc R A .
H83B H 0.5941 0.9906 0.3255 0.113 Uiso 1 1 calc R . .
H83C H 0.4751 1.0681 0.3448 0.113 Uiso 1 1 calc R . .
C63 C -0.1805(3) 0.6911(3) 0.1128(3) 0.0715(9) Uani 1 1 d . . .
H63A H -0.2393 0.6049 0.0553 0.107 Uiso 1 1 calc R A .
H63B H -0.1844 0.7662 0.0701 0.107 Uiso 1 1 calc R . .
H63C H -0.2406 0.6887 0.1684 0.107 Uiso 1 1 calc R . .
O13A O 0.0986(9) 0.9416(6) 0.1491(5) 0.0720(16) Uani 0.698(9) 1 d PDU A 1
C73A C 0.0757(12) 1.0312(9) 0.2311(9) 0.189(7) Uani 0.698(9) 1 d PDU A 1
H73A H 0.1022 1.0041 0.3093 0.283 Uiso 0.698(9) 1 calc PR A 1
H73B H -0.0460 1.0250 0.1999 0.283 Uiso 0.698(9) 1 calc PR A 1
H73C H 0.1554 1.1250 0.2396 0.283 Uiso 0.698(9) 1 calc PR A 1
O13B O 0.1046(19) 0.9636(12) 0.2038(12) 0.056(3) Uani 0.302(9) 1 d PDU A 2
C73B C 0.1754(15) 1.0674(10) 0.1456(10) 0.067(3) Uani 0.302(9) 1 d PDU A 2
H73D H 0.0806 1.0894 0.0911 0.100 Uiso 0.302(9) 1 calc PR A 2
H73E H 0.2334 1.0358 0.1001 0.100 Uiso 0.302(9) 1 calc PR A 2
H73F H 0.2613 1.1488 0.2054 0.100 Uiso 0.302(9) 1 calc PR A 2
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'
S S 0.1246 0.1234 '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'
Cu Cu 0.3201 1.2651 '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_3
N21 Cu N13 88.58(6) .
N21 Cu Cl1 150.16(6) .
N13 Cu Cl1 90.54(5) .
N21 Cu Cl2 91.76(5) .
N13 Cu Cl2 171.76(5) .
Cl1 Cu Cl2 93.24(2) .
N21 Cu Cl2 101.01(5) 2_666
N13 Cu Cl2 87.11(5) 2_666
Cl1 Cu Cl2 108.73(3) 2_666
Cl2 Cu Cl2 84.74(2) 2_666
Cu Cl2 Cu 95.26(2) 2_666
C22 S12 C32 100.48(12) .
C53 N13 C13 118.07(17) .
C53 N13 Cu 115.81(13) .
C13 N13 Cu 126.11(13) .
N13 C13 C23 122.08(18) .
N13 C13 C12 116.76(17) .
C23 C13 C12 121.13(17) .
C31 N11 N21 110.77(16) .
C31 N11 C12 127.12(17) .
N21 N11 C12 121.72(14) .
C13 C23 C33 118.09(19) .
C13 C23 C63 122.4(2) .
C33 C23 C63 119.5(2) .
C11 N21 N11 105.47(15) .
C11 N21 Cu 131.38(14) .
N11 N21 Cu 122.51(12) .
C53 C43 C33 116.21(19) .
C53 C43 C83 120.3(2) .
C33 C43 C83 123.5(2) .
N13 C53 C43 125.03(19) .
N13 C53 H53 117.5 .
C43 C53 H53 117.5 .
O13A C33 C43 121.9(3) .
O13A C33 C23 116.7(3) .
C43 C33 C23 120.4(2) .
O13A C33 O13B 27.1(4) .
C43 C33 O13B 117.5(6) .
C23 C33 O13B 119.3(6) .
N21 C11 C21 110.5(2) .
N21 C11 H11 124.7 .
C21 C11 H11 124.7 .
C12 C22 S12 114.63(14) .
C12 C22 H22A 108.6 .
S12 C22 H22A 108.6 .
C12 C22 H22B 108.6 .
S12 C22 H22B 108.6 .
H22A C22 H22B 107.6 .
N11 C31 C21 107.65(19) .
N11 C31 H31 126.2 .
C21 C31 H31 126.2 .
N11 C12 C13 112.23(16) .
N11 C12 C22 111.80(17) .
C13 C12 C22 111.16(16) .
N11 C12 H12 107.1 .
C13 C12 H12 107.1 .
C22 C12 H12 107.1 .
S12 C32 H32A 109.5 .
S12 C32 H32B 109.5 .
H32A C32 H32B 109.5 .
S12 C32 H32C 109.5 .
H32A C32 H32C 109.5 .
H32B C32 H32C 109.5 .
C31 C21 C11 105.59(18) .
C31 C21 H21 127.2 .
C11 C21 H21 127.2 .
C43 C83 H83A 109.5 .
C43 C83 H83B 109.5 .
H83A C83 H83B 109.5 .
C43 C83 H83C 109.5 .
H83A C83 H83C 109.5 .
H83B C83 H83C 109.5 .
C23 C63 H63A 109.5 .
C23 C63 H63B 109.5 .
H63A C63 H63B 109.5 .
C23 C63 H63C 109.5 .
H63A C63 H63C 109.5 .
H63B C63 H63C 109.5 .
C33 O13A C73A 110.3(7) .
C73B O13B C33 119.9(9) .
O13B C73B H73D 109.5 .
O13B C73B H73E 109.5 .
H73D C73B H73E 109.5 .
O13B C73B H73F 109.5 .
H73D C73B H73F 109.5 .
H73E C73B H73F 109.5 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cu N21 1.9941(16) .
Cu N13 2.0378(17) .
Cu Cl1 2.2553(6) .
Cu Cl2 2.2811(6) .
Cu Cl2 2.7524(7) 2_666
Cl2 Cu 2.7524(7) 2_666
S12 C22 1.797(2) .
S12 C32 1.801(3) .
N13 C53 1.342(3) .
N13 C13 1.350(2) .
C13 C23 1.384(3) .
C13 C12 1.520(3) .
N11 C31 1.347(2) .
N11 N21 1.362(2) .
N11 C12 1.453(2) .
C23 C33 1.405(3) .
C23 C63 1.512(3) .
N21 C11 1.339(3) .
C43 C53 1.372(3) .
C43 C33 1.400(3) .
C43 C83 1.510(3) .
C53 H53 0.9300 .
C33 O13A 1.359(6) .
C33 O13B 1.422(11) .
C11 C21 1.392(3) .
C11 H11 0.9300 .
C22 C12 1.536(3) .
C22 H22A 0.9700 .
C22 H22B 0.9700 .
C31 C21 1.366(3) .
C31 H31 0.9300 .
C12 H12 0.9800 .
C32 H32A 0.9600 .
C32 H32B 0.9600 .
C32 H32C 0.9600 .
C21 H21 0.9300 .
C83 H83A 0.9600 .
C83 H83B 0.9600 .
C83 H83C 0.9600 .
C63 H63A 0.9600 .
C63 H63B 0.9600 .
C63 H63C 0.9600 .
O13A C73A 1.420(11) .
C73A H73A 0.9600 .
C73A H73B 0.9600 .
C73A H73C 0.9600 .
O13B C73B 1.390(13) .
C73B H73D 0.9600 .
C73B H73E 0.9600 .
C73B H73F 0.9600 .
