#------------------------------------------------------------------------------
#$Date: 2016-03-21 07:12:46 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178553 $
#$URL: svn://www.crystallography.net/cod/cif/4/06/61/4066153.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_4066153
loop_
_publ_author_name
'Al Thagfi, Jameel'
'Dastgir, Sarim'
'Lough, Alan J.'
'Lavoie, Gino G.'
_publ_section_title
;
 Synthesis and Structural Characterization of the First Copper(I)
 Complexes with Bis(imino)-N-heterocyclic Carbene NCN Pincer Ligands
;
_journal_issue                   14
_journal_name_full               Organometallics
_journal_page_first              3133
_journal_paper_doi               10.1021/om100321n
_journal_volume                  29
_journal_year                    2010
_chemical_formula_moiety         'C46 H52 Cu2 I2 N8, 2(C H2 Cl2)'
_chemical_formula_sum            'C48 H56 Cl4 Cu2 I2 N8'
_chemical_formula_weight         1267.69
_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                87.1930(15)
_cell_angle_beta                 73.0400(13)
_cell_angle_gamma                80.1890(13)
_cell_formula_units_Z            1
_cell_length_a                   9.3771(2)
_cell_length_b                   10.1743(3)
_cell_length_c                   14.8030(4)
_cell_measurement_reflns_used    12467
_cell_measurement_temperature    150(1)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      2.8
_cell_volume                     1331.11(6)
_computing_cell_refinement       'Denzo-SMN (Otwinowski & Minor, 1997)'
_computing_data_collection       'Collect (Nonius B.V., 1997-2002)'
_computing_data_reduction        Denzo-SMN
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXTL V6.1'
_computing_structure_refinement  'SHELXTL V6.1 (Sheldrick, 2008)'
_computing_structure_solution    'SIR-92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      150(1)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'φ scans and ω scans with κ offsets'
_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  0.0402
_diffrn_reflns_av_sigmaI/netI    0.0562
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            12467
_diffrn_reflns_theta_full        25.24
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         2.81
_exptl_absorpt_coefficient_mu    2.199
_exptl_absorpt_correction_T_max  0.813
_exptl_absorpt_correction_T_min  0.698
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
multi-scan from symmetry-related measurements 
Sortav (Blessing 1995)
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.581
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_refine_diff_density_max         1.966
_refine_diff_density_min         -1.403
_refine_diff_density_rms         0.131
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     295
_refine_ls_number_reflns         6014
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0736
_refine_ls_R_factor_gt           0.0466
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0567P)²+2.1966P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1081
_refine_ls_wR_factor_ref         0.1272
_reflns_number_gt                4452
_reflns_number_total             6014
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            om100321n_si_002.cif
_cod_data_source_block           k1022
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               4066153
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
I1 I 0.83351(3) 0.37059(3) 0.08162(2) 0.03481(12) Uani 1 1 d .
Cu1 Cu 1.09642(6) 0.45199(5) 0.04748(4) 0.02714(14) Uani 1 1 d .
N1 N 1.2879(4) 0.3235(4) 0.1520(2) 0.0245(7) Uani 1 1 d .
N2 N 1.1320(4) 0.4648(4) 0.2502(2) 0.0259(8) Uani 1 1 d .
N3 N 1.2943(4) 0.2798(3) 0.0012(2) 0.0240(7) Uani 1 1 d .
N4 N 0.9605(5) 0.5627(4) 0.3814(3) 0.0342(9) Uani 1 1 d .
C1 C 1.1696(5) 0.4263(4) 0.1583(3) 0.0243(9) Uani 1 1 d .
C2 C 1.3235(5) 0.3016(5) 0.2375(3) 0.0315(10) Uani 1 1 d .
H2A H 1.4024 0.2375 0.2493 0.038 Uiso 1 1 calc R
C3 C 1.2249(5) 0.3883(5) 0.2992(3) 0.0326(10) Uani 1 1 d .
H3A H 1.2186 0.3968 0.3639 0.039 Uiso 1 1 calc R
C4 C 1.3602(4) 0.2541(4) 0.0643(3) 0.0247(9) Uani 1 1 d .
C5 C 1.5026(5) 0.1603(5) 0.0613(3) 0.0337(10) Uani 1 1 d .
H5A H 1.5465 0.1211 -0.0019 0.051 Uiso 1 1 calc R
H5B H 1.4801 0.0893 0.1079 0.051 Uiso 1 1 calc R
H5C H 1.5746 0.2091 0.0761 0.051 Uiso 1 1 calc R
C6 C 1.0087(5) 0.5673(4) 0.2924(3) 0.0279(9) Uani 1 1 d .
C7 C 0.9582(5) 0.6677(5) 0.2273(3) 0.0365(11) Uani 1 1 d .
H7A H 0.8890 0.7424 0.2639 0.055 Uiso 1 1 calc R
H7B H 0.9061 0.6265 0.1903 0.055 Uiso 1 1 calc R
H7C H 1.0462 0.7004 0.1845 0.055 Uiso 1 1 calc R
C8 C 0.8384(6) 0.6602(5) 0.4309(3) 0.0344(11) Uani 1 1 d .
C9 C 0.8699(6) 0.7657(5) 0.4755(3) 0.0395(12) Uani 1 1 d .
C10 C 0.7482(7) 0.8543(5) 0.5291(4) 0.0474(14) Uani 1 1 d .
H10A H 0.7670 0.9268 0.5597 0.057 Uiso 1 1 calc R
C11 C 0.6021(7) 0.8394(6) 0.5389(4) 0.0507(15) Uani 1 1 d .
H11A H 0.5209 0.9011 0.5760 0.061 Uiso 1 1 calc R
C12 C 0.5724(6) 0.7351(6) 0.4950(4) 0.0464(13) Uani 1 1 d .
H12A H 0.4706 0.7252 0.5025 0.056 Uiso 1 1 calc R
C13 C 0.6901(6) 0.6438(5) 0.4395(3) 0.0417(12) Uani 1 1 d .
C14 C 1.0307(7) 0.7786(6) 0.4645(4) 0.0530(15) Uani 1 1 d .
H14A H 1.0335 0.8500 0.5057 0.080 Uiso 1 1 calc R
H14B H 1.0799 0.7999 0.3987 0.080 Uiso 1 1 calc R
H14C H 1.0840 0.6943 0.4820 0.080 Uiso 1 1 calc R
C15 C 0.6569(6) 0.5324(6) 0.3893(4) 0.0536(15) Uani 1 1 d .
H15A H 0.7132 0.4473 0.4033 0.080 Uiso 1 1 calc R
H15B H 0.6876 0.5484 0.3210 0.080 Uiso 1 1 calc R
H15C H 0.5484 0.5290 0.4108 0.080 Uiso 1 1 calc R
C16 C 1.3640(5) 0.2260(4) -0.0921(3) 0.0275(9) Uani 1 1 d .
C17 C 1.4862(5) 0.2786(5) -0.1526(3) 0.0337(10) Uani 1 1 d .
C18 C 1.5433(6) 0.2304(6) -0.2454(4) 0.0460(13) Uani 1 1 d .
H18A H 1.6246 0.2659 -0.2882 0.055 Uiso 1 1 calc R
C19 C 1.4833(7) 0.1328(6) -0.2752(4) 0.0509(15) Uani 1 1 d .
H19A H 1.5247 0.0999 -0.3380 0.061 Uiso 1 1 calc R
C20 C 1.3642(6) 0.0822(5) -0.2153(4) 0.0461(14) Uani 1 1 d .
H20A H 1.3242 0.0145 -0.2374 0.055 Uiso 1 1 calc R
C21 C 1.2998(5) 0.1277(5) -0.1222(4) 0.0343(11) Uani 1 1 d .
C22 C 1.5535(5) 0.3852(5) -0.1211(4) 0.0405(12) Uani 1 1 d .
H22A H 1.4730 0.4479 -0.0793 0.061 Uiso 1 1 calc R
H22B H 1.6066 0.4331 -0.1763 0.061 Uiso 1 1 calc R
H22C H 1.6250 0.3443 -0.0869 0.061 Uiso 1 1 calc R
C23 C 1.1676(5) 0.0746(5) -0.0569(4) 0.0447(13) Uani 1 1 d .
H23A H 1.1936 0.0385 -0.0001 0.067 Uiso 1 1 calc R
H23B H 1.1417 0.0038 -0.0888 0.067 Uiso 1 1 calc R
H23C H 1.0809 0.1468 -0.0390 0.067 Uiso 1 1 calc R
Cl1 Cl 1.1533(3) 0.0121(2) 0.22621(16) 0.0861(6) Uani 1 1 d .
Cl2 Cl 0.8424(2) 0.0937(2) 0.34118(13) 0.0876(7) Uani 1 1 d .
C1S C 1.0008(8) 0.1442(8) 0.2610(6) 0.082(2) Uani 1 1 d .
H1SA H 1.0327 0.2154 0.2901 0.099 Uiso 1 1 calc R
H1SB H 0.9730 0.1822 0.2044 0.099 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'
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'
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
Cu1 I1 Cu1 60.65(2) 2_765 .
C1 Cu1 N3 77.86(15) . .
C1 Cu1 I1 124.85(12) . 2_765
N3 Cu1 I1 102.89(9) . 2_765
C1 Cu1 Cu1 155.29(13) . 2_765
N3 Cu1 Cu1 126.19(9) . 2_765
I1 Cu1 Cu1 60.65(2) 2_765 2_765
C1 Cu1 I1 110.38(12) . .
N3 Cu1 I1 111.83(9) . .
I1 Cu1 I1 119.35(2) 2_765 .
Cu1 Cu1 I1 58.70(2) 2_765 .
C1 N1 C2 112.1(4) . .
C1 N1 C4 120.1(3) . .
C2 N1 C4 127.9(4) . .
C1 N2 C3 111.9(4) . .
C1 N2 C6 123.8(4) . .
C3 N2 C6 124.2(4) . .
C4 N3 C16 120.2(3) . .
C4 N3 Cu1 110.5(3) . .
C16 N3 Cu1 127.7(3) . .
C6 N4 C8 119.9(4) . .
N2 C1 N1 102.7(3) . .
N2 C1 Cu1 141.3(3) . .
N1 C1 Cu1 115.3(3) . .
C3 C2 N1 106.4(4) . .
C2 C3 N2 106.9(4) . .
N3 C4 N1 115.6(4) . .
N3 C4 C5 129.2(4) . .
N1 C4 C5 115.2(4) . .
N4 C6 N2 115.1(4) . .
N4 C6 C7 128.4(4) . .
N2 C6 C7 116.4(4) . .
C13 C8 C9 121.5(5) . .
C13 C8 N4 119.5(4) . .
C9 C8 N4 118.9(5) . .
C10 C9 C8 117.9(5) . .
C10 C9 C14 122.6(5) . .
C8 C9 C14 119.5(5) . .
C11 C10 C9 121.5(5) . .
C10 C11 C12 120.2(5) . .
C11 C12 C13 120.8(5) . .
C8 C13 C12 118.2(5) . .
C8 C13 C15 121.3(5) . .
C12 C13 C15 120.5(5) . .
C21 C16 C17 121.8(4) . .
C21 C16 N3 118.2(4) . .
C17 C16 N3 119.8(4) . .
C18 C17 C16 118.0(5) . .
C18 C17 C22 120.1(5) . .
C16 C17 C22 121.9(4) . .
C19 C18 C17 120.8(5) . .
C20 C19 C18 120.6(5) . .
C19 C20 C21 121.5(5) . .
C20 C21 C16 117.3(5) . .
C20 C21 C23 121.8(5) . .
C16 C21 C23 121.0(4) . .
Cl2 C1S Cl1 112.5(4) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
I1 Cu1 2.5838(6) 2_765
I1 Cu1 2.6357(6) .
Cu1 C1 1.945(4) .
Cu1 N3 2.292(3) .
Cu1 I1 2.5838(6) 2_765
Cu1 Cu1 2.6357(10) 2_765
N1 C1 1.374(5) .
N1 C2 1.398(5) .
N1 C4 1.435(5) .
N2 C1 1.362(5) .
N2 C3 1.404(5) .
N2 C6 1.430(6) .
N3 C4 1.257(5) .
N3 C16 1.435(5) .
N4 C6 1.263(6) .
N4 C8 1.423(6) .
C2 C3 1.333(7) .
C4 C5 1.494(6) .
C6 C7 1.484(6) .
C8 C13 1.397(7) .
C8 C9 1.402(7) .
C9 C10 1.392(7) .
C9 C14 1.497(8) .
C10 C11 1.369(8) .
C11 C12 1.379(8) .
C12 C13 1.397(7) .
C13 C15 1.508(8) .
C16 C21 1.402(6) .
C16 C17 1.402(7) .
C17 C18 1.401(7) .
C17 C22 1.499(7) .
C18 C19 1.369(8) .
C19 C20 1.368(8) .
C20 C21 1.401(7) .
C21 C23 1.497(7) .
Cl1 C1S 1.761(8) .
Cl2 C1S 1.747(7) .
