#------------------------------------------------------------------------------
#$Date: 2021-04-18 01:53:29 +0300 (Sun, 18 Apr 2021) $
#$Revision: 264279 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/18/1561876.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_1561876
loop_
_publ_author_name
'Gou, Yi'
'Chen, MeiRong'
'Li, Shanhe'
'Deng, JunGang'
'Li, Jinlong'
'Fang, GuiHua'
'Yang, Feng'
'Huang, GuoJin'
_publ_section_title
;
 Dithiocarbazate-Copper Complexes for Bioimaging and Treatment of
 Pancreatic Cancer.
;
_journal_name_full               'Journal of medicinal chemistry'
_journal_paper_doi               10.1021/acs.jmedchem.0c01936
_journal_year                    2021
_chemical_formula_moiety         'C13 H11 Cl Cu N4 S2'
_chemical_formula_sum            'C13 H11 Cl Cu N4 S2'
_chemical_formula_weight         386.37
_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   geom
_atom_sites_solution_primary     heavy
_atom_sites_solution_secondary   difmap
_audit_creation_date             2019-09-30
_audit_creation_method
;
Olex2 1.2
(compiled 2016.08.25 svn.r3337 for OlexSys, GUI svn.r5221)
;
_cell_angle_alpha                68.887(5)
_cell_angle_beta                 71.065(5)
_cell_angle_gamma                82.137(6)
_cell_formula_units_Z            2
_cell_length_a                   8.6462(14)
_cell_length_b                   9.7989(15)
_cell_length_c                   10.1011(18)
_cell_measurement_reflns_used    10444
_cell_measurement_temperature    296
_cell_measurement_theta_max      26.32
_cell_measurement_theta_min      3.04
_cell_volume                     755.0(2)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      296
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'SuperNova, Single source at offset), Eos'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.70932
_diffrn_reflns_av_R_equivalents  0.0609
_diffrn_reflns_av_unetI/netI     0.0610
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            10444
_diffrn_reflns_theta_full        26.32
_diffrn_reflns_theta_max         26.32
_diffrn_reflns_theta_min         3.04
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    1.896
_exptl_absorpt_correction_T_max  0.7641
_exptl_absorpt_correction_T_min  0.6805
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            'dark blue'
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    blue
_exptl_crystal_density_diffrn    1.700
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             390
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.917
_refine_diff_density_min         -2.272
_refine_diff_density_rms         0.164
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.116
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         3079
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.116
_refine_ls_R_factor_all          0.1097
_refine_ls_R_factor_gt           0.0887
_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)+(0.1593P)²+1.8714P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2520
_refine_ls_wR_factor_ref         0.2749
_reflns_number_gt                2355
_reflns_number_total             3079
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jm0c01936_si_003.cif
_cod_data_source_block           shelx
_cod_database_code               1561876
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C5(H5), C10(H10), C13(H13), C6(H6), C12(H12), C11(H11), C8(H8), C7(H7)
2.b Idealised Me refined as rotating group:
 C1(H1a,H1b,H1c)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
Cu1 Cu 0.69329(11) 0.52878(10) 0.00796(10) 0.0436(4) Uani 1 d . . .
Cl1 Cl 0.4958(3) 0.3843(2) 0.1926(2) 0.0538(6) Uani 1 d . . .
S1 S 0.8330(3) 0.3477(2) -0.0739(2) 0.0536(6) Uani 1 d . . .
N2 N 0.8814(8) 0.6474(7) -0.1338(7) 0.0425(15) Uani 1 d . . .
S2 S 1.1243(3) 0.3762(3) -0.3251(3) 0.0642(7) Uani 1 d . . .
C2 C 0.9815(10) 0.4619(9) -0.2115(8) 0.0447(18) Uani 1 d . . .
N1 N 1.0007(8) 0.5985(7) -0.2366(7) 0.0478(16) Uani 1 d . . .
N4 N 0.6395(8) 0.7139(7) 0.0613(7) 0.0432(15) Uani 1 d . . .
C3 C 0.8834(9) 0.7801(8) -0.1399(8) 0.0398(16) Uani 1 d . . .
C9 C 0.7510(9) 0.8181(9) -0.0201(8) 0.0423(17) Uani 1 d . . .
N3 N 0.9373(9) 1.0219(7) -0.3165(7) 0.0512(17) Uani 1 d . . .
C4 C 1.0031(9) 0.8917(8) -0.2550(8) 0.0415(17) Uani 1 d . . .
C5 C 1.1691(10) 0.8567(9) -0.2984(9) 0.0483(19) Uani 1 d . . .
H5 H 1.2097 0.7660 -0.2503 0.058 Uiso 1 calc . . R
C10 C 0.7440(11) 0.9461(9) 0.0100(9) 0.0502(19) Uani 1 d . . .
H10 H 0.8245 1.0157 -0.0455 0.060 Uiso 1 calc . . R
C13 C 0.5138(10) 0.7368(10) 0.1702(9) 0.051(2) Uani 1 d . . .
H13 H 0.4343 0.6659 0.2238 0.061 Uiso 1 calc . . R
C6 C 1.2711(12) 0.9591(11) -0.4137(11) 0.065(3) Uani 1 d . . .
H6 H 1.3825 0.9388 -0.4463 0.078 Uiso 1 calc . . R
C12 C 0.4979(12) 0.8635(11) 0.2058(9) 0.059(2) Uani 1 d . . .
H12 H 0.4101 0.8769 0.2831 0.071 Uiso 1 calc . . R
C11 C 0.6141(12) 0.9682(11) 0.1250(9) 0.058(2) Uani 1 d . . .
H11 H 0.6060 1.0537 0.1471 0.070 Uiso 1 calc . . R
C8 C 1.0413(13) 1.1191(10) -0.4282(10) 0.062(2) Uani 1 d . . .
H8 H 0.9992 1.2104 -0.4733 0.074 Uiso 1 calc . . R
C7 C 1.2057(14) 1.0930(11) -0.4806(10) 0.068(3) Uani 1 d . . .
H7 H 1.2720 1.1641 -0.5598 0.082 Uiso 1 calc . . R
C1 C 1.2618(14) 0.5192(12) -0.4530(12) 0.082(4) Uani 1 d . . .
H1A H 1.2068 0.5906 -0.5175 0.122 Uiso 1 calc . . GR
H1B H 1.3546 0.4788 -0.5113 0.122 Uiso 1 calc . . GR
H1C H 1.2978 0.5650 -0.3989 0.122 Uiso 1 calc . . GR
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'
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'
N N 0.0061 0.0033 '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'
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
Cl1 Cu1 S1 95.55(9) . . ?
N2 Cu1 Cl1 172.5(2) . . ?
N2 Cu1 S1 84.1(2) . . ?
N2 Cu1 N4 79.9(3) . . ?
N4 Cu1 Cl1 99.29(18) . . ?
N4 Cu1 S1 162.1(2) . . ?
C2 S1 Cu1 93.8(3) . . ?
N1 N2 Cu1 122.4(5) . . ?
C3 N2 Cu1 118.0(5) . . ?
C3 N2 N1 119.2(6) . . ?
C2 S2 C1 103.4(4) . . ?
S1 C2 S2 113.8(5) . . ?
N1 C2 S1 128.1(6) . . ?
N1 C2 S2 118.1(6) . . ?
C2 N1 N2 110.6(6) . . ?
C9 N4 Cu1 113.6(5) . . ?
C13 N4 Cu1 127.0(6) . . ?
C13 N4 C9 119.2(7) . . ?
N2 C3 C9 114.0(6) . . ?
N2 C3 C4 125.2(7) . . ?
C9 C3 C4 120.9(7) . . ?
N4 C9 C3 113.9(7) . . ?
N4 C9 C10 122.0(7) . . ?
C10 C9 C3 124.1(7) . . ?
C8 N3 C4 115.9(8) . . ?
N3 C4 C3 115.2(7) . . ?
N3 C4 C5 123.8(7) . . ?
C5 C4 C3 120.9(7) . . ?
C6 C5 C4 118.4(8) . . ?
C9 C10 C11 118.4(8) . . ?
N4 C13 C12 121.9(8) . . ?
C5 C6 C7 118.8(9) . . ?
C11 C12 C13 118.7(8) . . ?
C12 C11 C10 119.7(9) . . ?
N3 C8 C7 124.3(9) . . ?
C8 C7 C6 118.8(8) . . ?
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
Cu1 Cl1 2.257(2) . ?
Cu1 S1 2.261(2) . ?
Cu1 N2 1.963(6) . ?
Cu1 N4 2.026(7) . ?
S1 C2 1.717(8) . ?
N2 N1 1.379(9) . ?
N2 C3 1.281(10) . ?
S2 C2 1.743(8) . ?
S2 C1 1.789(10) . ?
C2 N1 1.294(10) . ?
N4 C9 1.341(10) . ?
N4 C13 1.333(10) . ?
C3 C9 1.491(10) . ?
C3 C4 1.494(10) . ?
C9 C10 1.382(11) . ?
N3 C4 1.341(10) . ?
N3 C8 1.338(11) . ?
C4 C5 1.391(11) . ?
C5 C6 1.369(11) . ?
C10 C11 1.388(12) . ?
C13 C12 1.391(13) . ?
C6 C7 1.380(15) . ?
C12 C11 1.369(14) . ?
C8 C7 1.369(15) . ?
