#------------------------------------------------------------------------------
#$Date: 2016-02-14 06:40:26 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176432 $
#$URL: svn://www.crystallography.net/cod/cif/4/06/52/4065228.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_4065228
loop_
_publ_author_name
'Slivarichova, Miriam'
'Ahmad, Ruaa'
'Kuo, Yu-Ying'
'Nunn, Joshua'
'Haddow, Mairi F.'
'Othman, Hafiizah'
'Owen, Gareth R.'
_publ_section_title
;
 New Mixed-Donor Bidentate Ligands Based on N-Heterocyclic Carbene and
 Thione Donors
;
_journal_issue                   17
_journal_name_full               Organometallics
_journal_page_first              4779
_journal_paper_doi               10.1021/om200629j
_journal_volume                  30
_journal_year                    2011
_chemical_formula_moiety         'C42 H40 Cu2 I2 N8 S2'
_chemical_formula_sum            'C42 H40 Cu2 I2 N8 S2'
_chemical_formula_weight         1101.82
_chemical_name_common            ms74_0m
_chemical_name_systematic
; 
 ? 
;
_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                106.642(2)
_cell_angle_beta                 94.523(2)
_cell_angle_gamma                101.486(2)
_cell_formula_units_Z            1
_cell_length_a                   9.6138(4)
_cell_length_b                   10.0759(5)
_cell_length_c                   11.2954(6)
_cell_measurement_reflns_used    7962
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.58
_cell_measurement_theta_min      2.40
_cell_volume                     1016.52(9)
_computing_cell_refinement       'Bruker Apex II'
_computing_data_collection       'Bruker Apex II'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker ShelXTL'
_computing_publication_material  'Bruker ShelXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker Apex II kappa CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0253
_diffrn_reflns_av_sigmaI/netI    0.0237
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            18005
_diffrn_reflns_theta_full        27.62
_diffrn_reflns_theta_max         27.62
_diffrn_reflns_theta_min         1.90
_exptl_absorpt_coefficient_mu    2.710
_exptl_absorpt_correction_T_max  0.5403
_exptl_absorpt_correction_T_min  0.4744
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2008/1'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.800
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.842
_refine_diff_density_min         -0.488
_refine_diff_density_rms         0.081
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         4723
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0255
_refine_ls_R_factor_gt           0.0216
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0261P)²+0.5351P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0510
_refine_ls_wR_factor_ref         0.0528
_reflns_number_gt                4270
_reflns_number_total             4723
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om200629j_si_002.cif
_cod_data_source_block           Complex_4
_cod_original_sg_symbol_Hall     -P1
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               4065228
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
Cu1 Cu 0.58493(3) 0.67995(3) 0.60226(3) 0.01911(7) Uani 1 1 d .
I1 I 0.857172(14) 0.742506(14) 0.581848(13) 0.01906(5) Uani 1 1 d .
N2 N 0.21835(18) 0.61024(18) 0.38444(16) 0.0138(3) Uani 1 1 d .
N1 N 0.25363(19) 0.54941(18) 0.19146(16) 0.0146(3) Uani 1 1 d .
N3 N 0.33126(18) 0.79581(18) 0.57289(15) 0.0136(3) Uani 1 1 d .
N4 N 0.51124(19) 0.96828(19) 0.65953(16) 0.0161(4) Uani 1 1 d .
S1 S 0.47663(5) 0.53552(6) 0.35052(5) 0.01557(11) Uani 1 1 d .
C1 C 0.3145(2) 0.5664(2) 0.30901(19) 0.0137(4) Uani 1 1 d .
C2 C 0.3218(2) 0.5099(2) 0.07902(19) 0.0184(4) Uani 1 1 d .
H2A H 0.4235 0.5120 0.1038 0.022 Uiso 1 1 calc R
H2B H 0.3198 0.5811 0.0344 0.022 Uiso 1 1 calc R
C3 C 0.1190(2) 0.5789(2) 0.1938(2) 0.0174(4) Uani 1 1 d .
H3 H 0.0542 0.5731 0.1235 0.021 Uiso 1 1 calc R
C4 C 0.0969(2) 0.6171(2) 0.3134(2) 0.0162(4) Uani 1 1 d .
H4 H 0.0139 0.6438 0.3438 0.019 Uiso 1 1 calc R
C5 C 0.2424(2) 0.6524(2) 0.51998(18) 0.0145(4) Uani 1 1 d .
H5A H 0.1490 0.6477 0.5516 0.017 Uiso 1 1 calc R
H5B H 0.2897 0.5850 0.5470 0.017 Uiso 1 1 calc R
C6 C 0.4725(2) 0.8238(2) 0.62278(18) 0.0142(4) Uani 1 1 d .
C7 C 0.6527(2) 1.0518(2) 0.7242(2) 0.0184(4) Uani 1 1 d .
H7A H 0.6839 1.1284 0.6868 0.022 Uiso 1 1 calc R
H7B H 0.7212 0.9894 0.7096 0.022 Uiso 1 1 calc R
C8 C 0.3999(2) 1.0275(2) 0.6299(2) 0.0201(4) Uani 1 1 d .
H8 H 0.4037 1.1259 0.6451 0.024 Uiso 1 1 calc R
C9 C 0.2859(2) 0.9192(2) 0.5759(2) 0.0188(4) Uani 1 1 d .
H9 H 0.1932 0.9256 0.5458 0.023 Uiso 1 1 calc R
C10 C 0.2490(2) 0.3644(2) -0.00812(19) 0.0158(4) Uani 1 1 d .
C11 C 0.2078(2) 0.2502(2) 0.0375(2) 0.0187(4) Uani 1 1 d .
H11 H 0.2194 0.2650 0.1249 0.022 Uiso 1 1 calc R
C12 C 0.1499(2) 0.1152(2) -0.0442(2) 0.0260(5) Uani 1 1 d .
H12 H 0.1235 0.0373 -0.0128 0.031 Uiso 1 1 calc R
C13 C 0.1303(2) 0.0930(3) -0.1720(2) 0.0286(5) Uani 1 1 d .
H13 H 0.0902 0.0001 -0.2278 0.034 Uiso 1 1 calc R
C14 C 0.1690(3) 0.2060(3) -0.2179(2) 0.0265(5) Uani 1 1 d .
H14 H 0.1543 0.1909 -0.3054 0.032 Uiso 1 1 calc R
C15 C 0.2295(2) 0.3420(2) -0.1366(2) 0.0201(4) Uani 1 1 d .
H15 H 0.2576 0.4194 -0.1686 0.024 Uiso 1 1 calc R
C16 C 0.6611(2) 1.1190(2) 0.8643(2) 0.0161(4) Uani 1 1 d .
C17 C 0.7974(2) 1.1726(2) 0.9341(2) 0.0201(4) Uani 1 1 d .
H17 H 0.8793 1.1631 0.8933 0.024 Uiso 1 1 calc R
C18 C 0.8159(2) 1.2395(2) 1.0617(2) 0.0224(5) Uani 1 1 d .
H18 H 0.9097 1.2755 1.1078 0.027 Uiso 1 1 calc R
C19 C 0.6967(2) 1.2536(2) 1.1220(2) 0.0209(5) Uani 1 1 d .
H19 H 0.7084 1.3001 1.2093 0.025 Uiso 1 1 calc R
C20 C 0.5602(2) 1.1994(2) 1.0537(2) 0.0199(4) Uani 1 1 d .
H20 H 0.4785 1.2078 1.0949 0.024 Uiso 1 1 calc R
C21 C 0.5423(2) 1.1327(2) 0.9254(2) 0.0177(4) Uani 1 1 d .
H21 H 0.4485 1.0965 0.8795 0.021 Uiso 1 1 calc R
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'
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'
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
C6 Cu1 S1 126.06(6) . 2_666
C6 Cu1 I1 120.77(6) . .
S1 Cu1 I1 110.901(16) 2_666 .
C6 Cu1 S1 96.33(6) . .
S1 Cu1 S1 89.974(18) 2_666 .
I1 Cu1 S1 98.745(14) . .
C1 N2 C4 110.03(17) . .
C1 N2 C5 125.10(17) . .
C4 N2 C5 124.76(17) . .
C1 N1 C3 109.99(17) . .
C1 N1 C2 125.10(18) . .
C3 N1 C2 124.89(17) . .
C6 N3 C9 112.25(18) . .
C6 N3 C5 122.98(17) . .
C9 N3 C5 124.74(17) . .
C6 N4 C8 112.12(18) . .
C6 N4 C7 124.02(17) . .
C8 N4 C7 123.85(18) . .
C1 S1 Cu1 103.48(7) . 2_666
C1 S1 Cu1 111.96(7) . .
Cu1 S1 Cu1 90.025(18) 2_666 .
N1 C1 N2 105.53(17) . .
N1 C1 S1 126.45(16) . .
N2 C1 S1 128.01(15) . .
N1 C2 C10 112.56(18) . .
N1 C2 H2A 109.1 . .
C10 C2 H2A 109.1 . .
N1 C2 H2B 109.1 . .
C10 C2 H2B 109.1 . .
H2A C2 H2B 107.8 . .
C4 C3 N1 107.44(17) . .
C4 C3 H3 126.3 . .
N1 C3 H3 126.3 . .
C3 C4 N2 106.98(19) . .
C3 C4 H4 126.5 . .
N2 C4 H4 126.5 . .
N3 C5 N2 111.31(16) . .
N3 C5 H5A 109.4 . .
N2 C5 H5A 109.4 . .
N3 C5 H5B 109.4 . .
N2 C5 H5B 109.4 . .
H5A C5 H5B 108.0 . .
N4 C6 N3 102.66(17) . .
N4 C6 Cu1 131.96(15) . .
N3 C6 Cu1 123.90(15) . .
N4 C7 C16 115.16(18) . .
N4 C7 H7A 108.5 . .
C16 C7 H7A 108.5 . .
N4 C7 H7B 108.5 . .
C16 C7 H7B 108.5 . .
H7A C7 H7B 107.5 . .
C9 C8 N4 106.98(19) . .
C9 C8 H8 126.5 . .
N4 C8 H8 126.5 . .
C8 C9 N3 105.95(19) . .
C8 C9 H9 127.0 . .
N3 C9 H9 127.0 . .
C11 C10 C15 119.6(2) . .
C11 C10 C2 120.78(19) . .
C15 C10 C2 119.56(19) . .
C12 C11 C10 120.1(2) . .
C12 C11 H11 119.9 . .
C10 C11 H11 119.9 . .
C11 C12 C13 120.3(2) . .
C11 C12 H12 119.8 . .
C13 C12 H12 119.8 . .
C14 C13 C12 119.9(2) . .
C14 C13 H13 120.0 . .
C12 C13 H13 120.0 . .
C13 C14 C15 120.3(2) . .
C13 C14 H14 119.9 . .
C15 C14 H14 119.9 . .
C14 C15 C10 119.8(2) . .
C14 C15 H15 120.1 . .
C10 C15 H15 120.1 . .
C21 C16 C17 118.7(2) . .
C21 C16 C7 124.11(19) . .
C17 C16 C7 117.19(19) . .
C18 C17 C16 121.3(2) . .
C18 C17 H17 119.3 . .
C16 C17 H17 119.3 . .
C17 C18 C19 119.7(2) . .
C17 C18 H18 120.2 . .
C19 C18 H18 120.2 . .
C20 C19 C18 119.6(2) . .
C20 C19 H19 120.2 . .
C18 C19 H19 120.2 . .
C19 C20 C21 120.5(2) . .
C19 C20 H20 119.7 . .
C21 C20 H20 119.7 . .
C16 C21 C20 120.2(2) . .
C16 C21 H21 119.9 . .
C20 C21 H21 119.9 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cu1 C6 1.948(2) .
Cu1 S1 2.3557(6) 2_666
Cu1 I1 2.6119(3) .
Cu1 S1 2.8012(6) .
N2 C1 1.359(3) .
N2 C4 1.389(2) .
N2 C5 1.453(2) .
N1 C1 1.357(3) .
N1 C3 1.385(3) .
N1 C2 1.465(3) .
N3 C6 1.369(3) .
N3 C9 1.389(3) .
N3 C5 1.452(3) .
N4 C6 1.358(3) .
N4 C8 1.387(3) .
N4 C7 1.458(3) .
S1 C1 1.705(2) .
S1 Cu1 2.3557(6) 2_666
C2 C10 1.505(3) .
C2 H2A 0.9900 .
C2 H2B 0.9900 .
C3 C4 1.342(3) .
C3 H3 0.9500 .
C4 H4 0.9500 .
C5 H5A 0.9900 .
C5 H5B 0.9900 .
C7 C16 1.521(3) .
C7 H7A 0.9900 .
C7 H7B 0.9900 .
C8 C9 1.342(3) .
C8 H8 0.9500 .
C9 H9 0.9500 .
C10 C11 1.391(3) .
C10 C15 1.395(3) .
C11 C12 1.382(3) .
C11 H11 0.9500 .
C12 C13 1.387(4) .
C12 H12 0.9500 .
C13 C14 1.381(4) .
C13 H13 0.9500 .
C14 C15 1.392(3) .
C14 H14 0.9500 .
C15 H15 0.9500 .
C16 C21 1.391(3) .
C16 C17 1.393(3) .
C17 C18 1.385(3) .
C17 H17 0.9500 .
C18 C19 1.390(3) .
C18 H18 0.9500 .
C19 C20 1.388(3) .
C19 H19 0.9500 .
C20 C21 1.392(3) .
C20 H20 0.9500 .
C21 H21 0.9500 .
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_4
C6 Cu1 S1 C1 -21.74(10) . .
S1 Cu1 S1 C1 104.57(8) 2_666 .
I1 Cu1 S1 C1 -144.28(8) . .
C6 Cu1 S1 Cu1 -126.31(6) . 2_666
S1 Cu1 S1 Cu1 0.0 2_666 2_666
I1 Cu1 S1 Cu1 111.155(16) . 2_666
C3 N1 C1 N2 -1.6(2) . .
C2 N1 C1 N2 176.73(18) . .
C3 N1 C1 S1 177.40(16) . .
C2 N1 C1 S1 -4.3(3) . .
C4 N2 C1 N1 1.4(2) . .
C5 N2 C1 N1 -175.05(17) . .
C4 N2 C1 S1 -177.58(16) . .
C5 N2 C1 S1 6.0(3) . .
Cu1 S1 C1 N1 -105.22(18) 2_666 .
Cu1 S1 C1 N1 159.20(16) . .
Cu1 S1 C1 N2 73.51(19) 2_666 .
Cu1 S1 C1 N2 -22.1(2) . .
C1 N1 C2 C10 112.8(2) . .
C3 N1 C2 C10 -69.2(3) . .
C1 N1 C3 C4 1.2(2) . .
C2 N1 C3 C4 -177.11(19) . .
N1 C3 C4 N2 -0.3(2) . .
C1 N2 C4 C3 -0.7(2) . .
C5 N2 C4 C3 175.76(18) . .
C6 N3 C5 N2 -105.2(2) . .
C9 N3 C5 N2 72.8(2) . .
C1 N2 C5 N3 78.2(2) . .
C4 N2 C5 N3 -97.7(2) . .
C8 N4 C6 N3 -1.9(2) . .
C7 N4 C6 N3 177.23(18) . .
C8 N4 C6 Cu1 164.16(16) . .
C7 N4 C6 Cu1 -16.7(3) . .
C9 N3 C6 N4 1.6(2) . .
C5 N3 C6 N4 179.84(17) . .
C9 N3 C6 Cu1 -165.94(15) . .
C5 N3 C6 Cu1 12.3(3) . .
S1 Cu1 C6 N4 142.65(17) 2_666 .
I1 Cu1 C6 N4 -18.6(2) . .
S1 Cu1 C6 N4 -122.75(19) . .
S1 Cu1 C6 N3 -53.80(19) 2_666 .
I1 Cu1 C6 N3 144.94(14) . .
S1 Cu1 C6 N3 40.81(17) . .
C6 N4 C7 C16 -101.9(2) . .
C8 N4 C7 C16 77.1(3) . .
C6 N4 C8 C9 1.6(2) . .
C7 N4 C8 C9 -177.57(19) . .
N4 C8 C9 N3 -0.5(2) . .
C6 N3 C9 C8 -0.7(2) . .
C5 N3 C9 C8 -178.93(18) . .
N1 C2 C10 C11 -44.0(3) . .
N1 C2 C10 C15 139.5(2) . .
C15 C10 C11 C12 0.9(3) . .
C2 C10 C11 C12 -175.6(2) . .
C10 C11 C12 C13 -1.1(3) . .
C11 C12 C13 C14 0.2(3) . .
C12 C13 C14 C15 0.9(3) . .
C13 C14 C15 C10 -1.0(3) . .
C11 C10 C15 C14 0.1(3) . .
C2 C10 C15 C14 176.7(2) . .
N4 C7 C16 C21 -15.3(3) . .
N4 C7 C16 C17 166.24(18) . .
C21 C16 C17 C18 -0.5(3) . .
C7 C16 C17 C18 178.1(2) . .
C16 C17 C18 C19 0.1(3) . .
C17 C18 C19 C20 0.6(3) . .
C18 C19 C20 C21 -0.8(3) . .
C17 C16 C21 C20 0.2(3) . .
C7 C16 C21 C20 -178.22(19) . .
C19 C20 C21 C16 0.4(3) . .
