#------------------------------------------------------------------------------
#$Date: 2017-02-04 15:54:00 +0200 (Sat, 04 Feb 2017) $
#$Revision: 191616 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/04/15/7041588.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_7041588
loop_
_publ_author_name
'Aulakh, Jaspreet K.'
'Lobana, Tarlok S.'
'Sood, Henna'
'Arora, Daljit S.'
'Garcia-Santos, Isabel'
'Hundal, Geeta'
'Kaur, Manpreet'
'Smolenski, Victoria A.'
'Jasinski, Jerry P.'
_publ_section_title
;
 Variable coordination and C-S bond cleavage activity of N-substituted
 imidazolidine-2-thiones towards copper: synthesis, spectroscopy,
 structures, ESI-mass and antimicrobial studies.
;
_journal_issue                   4
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              1324
_journal_page_last               1339
_journal_paper_doi               10.1039/c6dt04103e
_journal_volume                  46
_journal_year                    2017
_chemical_formula_moiety         'C20 H36 Cu5 I6 N8 S2'
_chemical_formula_sum            'C20 H36 Cu5 I6 N8 S2'
_chemical_formula_weight         1531.79
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_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
_audit_creation_date             2016-07-13
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_audit_update_record
;
2016-09-29 deposited with the CCDC.
2016-12-26 downloaded from the CCDC.
;
_cell_angle_alpha                99.126(5)
_cell_angle_beta                 102.165(5)
_cell_angle_gamma                111.425(5)
_cell_formula_units_Z            1
_cell_length_a                   8.0690(4)
_cell_length_b                   9.9078(6)
_cell_length_c                   13.1167(8)
_cell_measurement_reflns_used    3786
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      32.2280
_cell_measurement_theta_min      3.1450
_cell_volume                     921.71(11)
_computing_cell_refinement
'CrysAlis PRO (Rigaku OxfordDiffraction, 2015)'
_computing_data_collection
'CrysAlis PRO (Rigaku OxfordDiffraction, 2015)'
_computing_data_reduction
'CrysAlis RED (Rigaku OxfordDiffraction, 2015)'
_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      173(2)
_diffrn_detector_area_resol_mean 16.0416
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.897
_diffrn_measurement_device_type  Rigaku-OxfordDiffracti0on
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0343
_diffrn_reflns_av_unetI/netI     0.0566
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.897
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            6080
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.897
_diffrn_reflns_theta_full        25.500
_diffrn_reflns_theta_max         32.706
_diffrn_reflns_theta_min         3.290
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    8.002
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.36790
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            black
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    2.760
_exptl_crystal_description       prism
_exptl_crystal_F_000             707
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.08
_refine_diff_density_max         3.114
_refine_diff_density_min         -2.036
_refine_diff_density_rms         0.248
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     189
_refine_ls_number_reflns         6080
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.0616
_refine_ls_R_factor_gt           0.0463
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0482P)²+2.1039P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1075
_refine_ls_wR_factor_ref         0.1201
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4853
_reflns_number_total             6080
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c6dt04103e2.cif
_cod_data_source_block           tsl-432
_cod_depositor_comments
'Adding full bibliography for 7041581--7041593.cif.'
_cod_original_cell_volume        921.71(10)
_cod_database_code               7041588
_shelxl_version_number           2014/6
_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.
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C3(H3A,H3B), C6(H6A,H6B), C7(H7A,H7B), C9(H9A,H9B)
2.b Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C), C10(H10A,H10B,H10C)
;
_olex2_exptl_crystal_mounting_method 'Nylon Loop'
_olex2_submission_original_sample_id TSL-432
_olex2_submission_special_instructions 'No special instructions were received'
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
I1 I 0.24158(5) 0.35074(4) 0.37989(3) 0.02170(9) Uani 1 1 d . . .
I2 I 0.60537(6) 0.75106(4) 0.30014(3) 0.02594(10) Uani 1 1 d . . .
I3 I 0.31469(6) 0.32176(4) 0.04104(3) 0.02734(10) Uani 1 1 d . . .
Cu1 Cu 1.0000 0.5000 0.5000 0.01752(18) Uani 1 2 d S T P
Cu2 Cu 0.58240(11) 0.55041(9) 0.40805(7) 0.03050(18) Uani 1 1 d . . .
Cu3 Cu 0.54781(12) 0.59935(9) 0.11181(7) 0.03146(18) Uani 1 1 d . . .
S1 S 0.72528(18) 0.38962(14) 0.35120(11) 0.0170(2) Uani 1 1 d . . .
N1 N 1.0820(7) 0.6789(5) 0.4460(4) 0.0178(9) Uani 1 1 d . . .
N2 N 1.1316(7) 0.8311(5) 0.3341(4) 0.0200(9) Uani 1 1 d . . .
N3 N 0.9610(6) 0.5698(5) 0.2557(4) 0.0169(8) Uani 1 1 d . . .
N4 N 0.7968(6) 0.3341(5) 0.1626(4) 0.0187(9) Uani 1 1 d . . .
C1 C 1.1884(11) 0.8342(6) 0.5163(5) 0.0336(15) Uani 1 1 d . . .
H1A H 1.3101 0.8457 0.5614 0.040 Uiso 1 1 calc R . .
H1B H 1.1180 0.8587 0.5643 0.040 Uiso 1 1 calc R . .
C2 C 1.2155(11) 0.9353(7) 0.4410(5) 0.0332(15) Uani 1 1 d . . .
H2A H 1.1519 1.0029 0.4510 0.040 Uiso 1 1 calc R . .
H2B H 1.3494 0.9966 0.4529 0.040 Uiso 1 1 calc R . .
C3 C 1.0737(8) 0.8847(6) 0.2411(5) 0.0234(11) Uani 1 1 d . . .
H3A H 1.0211 0.9571 0.2623 0.028 Uiso 1 1 calc R . .
H3B H 0.9749 0.7990 0.1831 0.028 Uiso 1 1 calc R . .
C4 C 1.2364(10) 0.9603(8) 0.1984(6) 0.0332(14) Uani 1 1 d . . .
H4A H 1.1934 0.9960 0.1368 0.050 Uiso 1 1 calc GR . .
H4B H 1.2863 0.8880 0.1753 0.050 Uiso 1 1 calc GR . .
H4C H 1.3341 1.0456 0.2555 0.050 Uiso 1 1 calc GR . .
C5 C 1.0527(7) 0.6893(5) 0.3466(4) 0.0149(9) Uani 1 1 d . . .
C6 C 1.0429(8) 0.5516(7) 0.1659(5) 0.0242(11) Uani 1 1 d . . .
H6A H 1.1660 0.5492 0.1920 0.029 Uiso 1 1 calc R . .
H6B H 1.0566 0.6336 0.1295 0.029 Uiso 1 1 calc R . .
C7 C 0.9005(9) 0.4009(7) 0.0906(5) 0.0243(11) Uani 1 1 d . . .
H7A H 0.8185 0.4143 0.0291 0.029 Uiso 1 1 calc R . .
H7B H 0.9619 0.3391 0.0628 0.029 Uiso 1 1 calc R . .
C8 C 0.8315(7) 0.4314(6) 0.2536(4) 0.0151(9) Uani 1 1 d . . .
C9 C 0.6684(8) 0.1748(6) 0.1299(5) 0.0240(11) Uani 1 1 d . . .
H9A H 0.5920 0.1486 0.0540 0.029 Uiso 1 1 calc R . .
H9B H 0.5834 0.1566 0.1756 0.029 Uiso 1 1 calc R . .
C10 C 0.7722(11) 0.0762(8) 0.1404(7) 0.0439(19) Uani 1 1 d . . .
H10A H 0.6852 -0.0290 0.1077 0.066 Uiso 1 1 calc GR . .
H10B H 0.8306 0.0897 0.2169 0.066 Uiso 1 1 calc GR . .
H10C H 0.8685 0.1039 0.1033 0.066 Uiso 1 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'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 '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
Cu2 I1 Cu2 71.81(3) . 2_666
Cu3 I2 Cu2 101.08(3) . .
Cu3 I3 Cu3 71.95(3) . 2_665
S1 Cu1 S1 180.0 . 2_766
N1 Cu1 S1 90.55(14) . 2_766
N1 Cu1 S1 89.45(14) 2_766 2_766
N1 Cu1 S1 90.55(14) 2_766 .
N1 Cu1 S1 89.45(14) . .
N1 Cu1 N1 180.0 2_766 .
I1 Cu2 I1 108.19(3) . 2_666
I2 Cu2 I1 117.14(3) . 2_666
I2 Cu2 I1 115.25(3) . .
S1 Cu2 I1 100.93(4) . 2_666
S1 Cu2 I1 100.74(4) . .
S1 Cu2 I2 112.47(5) . .
I2 Cu3 I3 130.17(4) . 2_665
I2 Cu3 I3 121.76(4) . .
I2 Cu3 Cu3 175.66(5) . 2_665
I3 Cu3 I3 108.05(3) . 2_665
I3 Cu3 Cu3 54.10(3) . 2_665
I3 Cu3 Cu3 53.96(3) 2_665 2_665
Cu1 S1 Cu2 96.89(5) . .
C8 S1 Cu1 96.85(17) . .
C8 S1 Cu2 115.74(18) . .
C1 N1 Cu1 124.1(4) . .
C5 N1 Cu1 129.0(4) . .
C5 N1 C1 106.9(4) . .
C2 N2 C3 119.3(5) . .
C5 N2 C2 107.9(4) . .
C5 N2 C3 126.8(5) . .
C5 N3 C6 122.2(4) . .
C8 N3 C5 124.3(4) . .
C8 N3 C6 108.8(4) . .
C8 N4 C7 112.9(4) . .
C8 N4 C9 126.5(5) . .
C9 N4 C7 120.6(5) . .
N1 C1 H1A 110.6 . .
N1 C1 H1B 110.6 . .
N1 C1 C2 105.9(5) . .
H1A C1 H1B 108.7 . .
C2 C1 H1A 110.6 . .
C2 C1 H1B 110.6 . .
N2 C2 C1 103.6(5) . .
N2 C2 H2A 111.0 . .
N2 C2 H2B 111.0 . .
C1 C2 H2A 111.0 . .
C1 C2 H2B 111.0 . .
H2A C2 H2B 109.0 . .
N2 C3 H3A 109.3 . .
N2 C3 H3B 109.3 . .
N2 C3 C4 111.5(5) . .
H3A C3 H3B 108.0 . .
C4 C3 H3A 109.3 . .
C4 C3 H3B 109.3 . .
C3 C4 H4A 109.5 . .
C3 C4 H4B 109.5 . .
C3 C4 H4C 109.5 . .
H4A C4 H4B 109.5 . .
H4A C4 H4C 109.5 . .
H4B C4 H4C 109.5 . .
N1 C5 N2 115.4(5) . .
N1 C5 N3 125.5(4) . .
N2 C5 N3 118.9(5) . .
N3 C6 H6A 111.2 . .
N3 C6 H6B 111.2 . .
N3 C6 C7 102.8(4) . .
H6A C6 H6B 109.1 . .
C7 C6 H6A 111.2 . .
C7 C6 H6B 111.2 . .
N4 C7 C6 101.8(4) . .
N4 C7 H7A 111.4 . .
N4 C7 H7B 111.4 . .
C6 C7 H7A 111.4 . .
C6 C7 H7B 111.4 . .
H7A C7 H7B 109.3 . .
N3 C8 S1 126.3(4) . .
N4 C8 S1 124.0(4) . .
N4 C8 N3 109.7(5) . .
N4 C9 H9A 109.4 . .
N4 C9 H9B 109.4 . .
N4 C9 C10 111.3(5) . .
H9A C9 H9B 108.0 . .
C10 C9 H9A 109.4 . .
C10 C9 H9B 109.4 . .
C9 C10 H10A 109.5 . .
C9 C10 H10B 109.5 . .
C9 C10 H10C 109.5 . .
H10A C10 H10B 109.5 . .
H10A C10 H10C 109.5 . .
H10B C10 H10C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
I1 Cu2 2.6417(9) .
I1 Cu2 2.6773(10) 2_666
I2 Cu2 2.5931(9) .
I2 Cu3 2.5309(10) .
I3 Cu3 2.5811(10) 2_665
I3 Cu3 2.5766(10) .
Cu1 S1 2.3765(14) .
Cu1 S1 2.3765(14) 2_766
Cu1 N1 1.955(4) 2_766
Cu1 N1 1.955(4) .
Cu2 I1 2.6773(9) 2_666
Cu2 S1 2.3980(16) .
Cu3 I3 2.5811(10) 2_665
Cu3 Cu3 3.0297(17) 2_665
S1 C8 1.708(5) .
N1 C1 1.485(7) .
N1 C5 1.302(7) .
N2 C2 1.456(8) .
N2 C3 1.461(7) .
N2 C5 1.368(6) .
N3 C5 1.382(7) .
N3 C6 1.485(7) .
N3 C8 1.379(6) .
N4 C7 1.468(7) .
N4 C8 1.316(7) .
N4 C9 1.467(7) .
C1 H1A 0.9900 .
C1 H1B 0.9900 .
C1 C2 1.506(8) .
C2 H2A 0.9900 .
C2 H2B 0.9900 .
C3 H3A 0.9900 .
C3 H3B 0.9900 .
C3 C4 1.525(8) .
C4 H4A 0.9800 .
C4 H4B 0.9800 .
C4 H4C 0.9800 .
C6 H6A 0.9900 .
C6 H6B 0.9900 .
C6 C7 1.525(8) .
C7 H7A 0.9900 .
C7 H7B 0.9900 .
C9 H9A 0.9900 .
C9 H9B 0.9900 .
C9 C10 1.506(9) .
C10 H10A 0.9800 .
C10 H10B 0.9800 .
C10 H10C 0.9800 .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C1 H1A S1 0.99 2.71 3.204(7) 111.4 2_766
C1 H1B I1 0.99 3.20 3.923(7) 131.1 2_666
C3 H3B I3 0.99 3.08 3.966(6) 149.7 2_665
C6 H6A I2 0.99 3.22 4.072(6) 144.9 1_655
C7 H7B I3 0.99 2.98 3.857(6) 147.8 1_655
C10 H10A I3 0.98 3.23 4.000(7) 136.8 2_655
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
Cu1 S1 C8 N3 -49.5(5)
Cu1 S1 C8 N4 132.1(4)
Cu1 N1 C1 C2 -178.2(5)
Cu1 N1 C5 N2 -178.8(4)
Cu1 N1 C5 N3 -3.3(8)
Cu2 S1 C8 N3 51.6(5)
Cu2 S1 C8 N4 -126.8(4)
N1 C1 C2 N2 -2.7(8)
N3 C6 C7 N4 -18.3(6)
C1 N1 C5 N2 3.2(7)
C1 N1 C5 N3 178.7(6)
C2 N2 C3 C4 83.3(7)
C2 N2 C5 N1 -5.1(7)
C2 N2 C5 N3 179.0(5)
C3 N2 C2 C1 159.2(6)
C3 N2 C5 N1 -157.3(5)
C3 N2 C5 N3 26.8(8)
C5 N1 C1 C2 -0.1(7)
C5 N2 C2 C1 4.5(7)
C5 N2 C3 C4 -127.3(6)
C5 N3 C6 C7 175.7(5)
C5 N3 C8 S1 13.6(8)
C5 N3 C8 N4 -167.8(5)
C6 N3 C5 N1 -128.4(6)
C6 N3 C5 N2 47.0(7)
C6 N3 C8 S1 169.8(4)
C6 N3 C8 N4 -11.7(6)
C7 N4 C8 S1 177.2(4)
C7 N4 C8 N3 -1.4(6)
C7 N4 C9 C10 76.6(7)
C8 N3 C5 N1 24.8(8)
C8 N3 C5 N2 -159.8(5)
C8 N3 C6 C7 19.0(6)
C8 N4 C7 C6 13.0(6)
C8 N4 C9 C10 -104.3(7)
C9 N4 C7 C6 -167.7(5)
C9 N4 C8 S1 -1.9(8)
C9 N4 C8 N3 179.5(5)
