#------------------------------------------------------------------------------
#$Date: 2017-02-03 22:10:06 +0200 (Fri, 03 Feb 2017) $
#$Revision: 191231 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/40/4514016.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_4514016
loop_
_publ_author_name
'Trose, Michael'
'Lazreg, Faïma'
'Chang, Tao'
'Nahra, Fady'
'Cordes, David B.'
'Slawin, Alexandra M. Z.'
'Cazin, Catherine S. J.'
_publ_section_title
;
 Neutral Dinuclear Copper(I)-NHC Complexes: Synthesis and Application in
 the Hydrosilylation of Ketones
;
_journal_issue                   1
_journal_name_full               'ACS Catalysis'
_journal_page_first              238
_journal_paper_doi               10.1021/acscatal.6b02723
_journal_volume                  7
_journal_year                    2017
_chemical_formula_moiety         'C46 H56 Cu2 N10'
_chemical_formula_sum            'C46 H56 Cu2 N10'
_chemical_formula_weight         876.11
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2015-11-09
_audit_creation_method           'by CrystalStructure 4.1'
_cell_angle_alpha                90.0000
_cell_angle_beta                 108.686(4)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            2
_cell_length_a                   11.3017(15)
_cell_length_b                   13.5088(15)
_cell_length_c                   14.966(2)
_cell_measurement_reflns_used    5097
_cell_measurement_temperature    173
_cell_measurement_theta_max      25.30
_cell_measurement_theta_min      1.90
_cell_volume                     2164.5(5)
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b32'
_computing_data_collection
'CrystalClear-SM Expert 2.1 b32 (Rigaku, 2014)'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b32'
_computing_molecular_graphics    'CrystalStructure 4.1'
_computing_publication_material  'CrystalStructure 4.1 (Rigaku, 2014)'
_computing_structure_refinement  'SHELXL2013 (Sheldrick, 2008)'
_computing_structure_solution    'SIR2011 (Burla, et al., 2012)'
_diffrn_ambient_temperature      173
_diffrn_detector_area_resol_mean 5.814
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ω
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0379
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            25768
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.336
_diffrn_reflns_theta_min         1.902
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.028
_exptl_absorpt_correction_T_max  0.940
_exptl_absorpt_correction_T_min  0.852
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.344
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             920.00
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.060
_refine_diff_density_max         0.30
_refine_diff_density_min         -0.27
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     268
_refine_ls_number_reflns         3935
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0422
_refine_ls_R_factor_gt           0.0315
_refine_ls_shift/su_max          0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0378P)²+1.6423P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0766
_refine_ls_wR_factor_ref         0.0816
_reflns_number_gt                3309
_reflns_number_total             3935
_reflns_threshold_expression     F²>2.0σ(F²)
_cod_data_source_file            cs6b02723_si_004.cif
_cod_data_source_block           2c
_cod_database_code               4514016
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,1/2+Y,1/2-Z
3 -X,-Y,-Z
4 +X,-1/2-Y,-1/2+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
Cu1 Cu 0.05942(2) 0.12559(2) 0.47923(2) 0.02563(10) Uani 1 1 d . .
N2 N 0.23922(15) 0.28193(12) 0.47813(12) 0.0217(4) Uani 1 1 d . .
N5 N 0.05169(15) 0.33703(12) 0.44721(13) 0.0227(4) Uani 1 1 d . .
N31 N 0.10629(17) 0.04939(13) 0.59951(13) 0.0274(4) Uani 1 1 d . .
N32 N 0.06711(17) -0.04426(13) 0.61223(13) 0.0282(4) Uani 1 1 d . .
N34 N 0.2211(2) -0.00245(18) 0.74319(15) 0.0499(6) Uani 1 1 d . .
C1 C 0.12061(18) 0.25366(15) 0.46494(14) 0.0208(4) Uani 1 1 d . .
C3 C 0.25136(19) 0.38823(14) 0.45856(17) 0.0271(5) Uani 1 1 d . .
H3A H 0.2620 0.3983 0.3960 0.033 Uiso 1 1 calc R U
H3B H 0.3222 0.4192 0.5077 0.033 Uiso 1 1 calc R U
C4 C 0.12752(19) 0.42820(15) 0.46090(17) 0.0279(5) Uani 1 1 d . .
H4A H 0.1355 0.4599 0.5222 0.033 Uiso 1 1 calc R U
H4B H 0.0918 0.4763 0.4094 0.033 Uiso 1 1 calc R U
C6 C 0.34135(18) 0.21853(14) 0.47886(15) 0.0225(5) Uani 1 1 d . .
C7 C 0.3387(2) 0.16724(16) 0.39756(16) 0.0271(5) Uani 1 1 d . .
C8 C 0.4459(2) 0.11665(16) 0.39718(18) 0.0331(5) Uani 1 1 d . .
H8 H 0.4450 0.0810 0.3422 0.040 Uiso 1 1 calc R U
C9 C 0.5537(2) 0.11665(16) 0.47447(18) 0.0338(6) Uani 1 1 d . .
C10 C 0.5519(2) 0.16708(17) 0.55389(18) 0.0323(5) Uani 1 1 d . .
H10 H 0.6247 0.1663 0.6078 0.039 Uiso 1 1 calc R U
C11 C 0.44755(19) 0.21933(16) 0.55848(16) 0.0274(5) Uani 1 1 d . .
C12 C 0.2251(2) 0.16754(19) 0.31071(17) 0.0366(6) Uani 1 1 d . .
H12A H 0.1968 0.2358 0.2949 0.044 Uiso 1 1 calc R U
H12B H 0.1584 0.1290 0.3227 0.044 Uiso 1 1 calc R U
H12C H 0.2464 0.1380 0.2580 0.044 Uiso 1 1 calc R U
C13 C 0.6701(2) 0.0652(2) 0.4702(2) 0.0475(7) Uani 1 1 d . .
H13A H 0.7009 0.0982 0.4237 0.057 Uiso 1 1 calc R U
H13B H 0.6507 -0.0041 0.4517 0.057 Uiso 1 1 calc R U
H13C H 0.7343 0.0678 0.5323 0.057 Uiso 1 1 calc R U
C14 C 0.4532(2) 0.2758(2) 0.64646(17) 0.0393(6) Uani 1 1 d . .
H14A H 0.3698 0.2783 0.6531 0.047 Uiso 1 1 calc R U
H14B H 0.4827 0.3433 0.6421 0.047 Uiso 1 1 calc R U
H14C H 0.5109 0.2426 0.7015 0.047 Uiso 1 1 calc R U
C15 C -0.07991(18) 0.34490(14) 0.42918(16) 0.0221(5) Uani 1 1 d . .
C16 C -0.1310(2) 0.32848(15) 0.50090(17) 0.0285(5) Uani 1 1 d . .
C17 C -0.2582(2) 0.34514(17) 0.4819(2) 0.0366(6) Uani 1 1 d . .
H17 H -0.2944 0.3333 0.5301 0.044 Uiso 1 1 calc R U
C18 C -0.3334(2) 0.37837(16) 0.3949(2) 0.0362(6) Uani 1 1 d . .
C19 C -0.2797(2) 0.39417(17) 0.32544(18) 0.0343(6) Uani 1 1 d . .
H19 H -0.3306 0.4174 0.2656 0.041 Uiso 1 1 calc R U
C20 C -0.1532(2) 0.37721(15) 0.34005(16) 0.0269(5) Uani 1 1 d . .
C21 C -0.0511(3) 0.2989(2) 0.59786(18) 0.0449(7) Uani 1 1 d . .
H21A H 0.0240 0.3404 0.6175 0.054 Uiso 1 1 calc R U
H21B H -0.0267 0.2293 0.5974 0.054 Uiso 1 1 calc R U
H21C H -0.0981 0.3076 0.6421 0.054 Uiso 1 1 calc R U
C22 C -0.4708(2) 0.3974(2) 0.3773(3) 0.0561(8) Uani 1 1 d . .
H22A H -0.5160 0.3343 0.3668 0.067 Uiso 1 1 calc R U
H22B H -0.5036 0.4395 0.3215 0.067 Uiso 1 1 calc R U
H22C H -0.4820 0.4307 0.4322 0.067 Uiso 1 1 calc R U
C23 C -0.0989(2) 0.3946(2) 0.26193(18) 0.0410(6) Uani 1 1 d . .
H23A H -0.0614 0.4607 0.2686 0.049 Uiso 1 1 calc R U
H23B H -0.1651 0.3896 0.2009 0.049 Uiso 1 1 calc R U
H23C H -0.0347 0.3446 0.2653 0.049 Uiso 1 1 calc R U
C33 C 0.1384(2) -0.0706(2) 0.69773(18) 0.0410(6) Uani 1 1 d . .
H33 H 0.1312 -0.1331 0.7246 0.049 Uiso 1 1 calc R U
C35 C 0.1964(2) 0.06961(19) 0.67900(18) 0.0386(6) Uani 1 1 d . .
H35 H 0.2401 0.1308 0.6895 0.046 Uiso 1 1 calc R U
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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
Cu Cu 0.3201 1.2651
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(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
C1 Cu1 N32 129.76(8) . 3_556
C1 Cu1 N31 124.82(8) . .
N32 Cu1 N31 105.29(7) 3_556 .
C1 N2 C6 126.35(17) . .
C1 N2 C3 113.40(16) . .
C6 N2 C3 117.08(16) . .
C1 N5 C15 126.96(17) . .
C1 N5 C4 113.38(16) . .
C15 N5 C4 119.16(16) . .
C35 N31 N32 104.77(19) . .
C35 N31 Cu1 127.66(16) . .
N32 N31 Cu1 126.65(14) . .
C33 N32 N31 104.95(19) . .
C33 N32 Cu1 127.17(16) . 3_556
N31 N32 Cu1 127.77(14) . 3_556
C35 N34 C33 100.7(2) . .
N2 C1 N5 106.11(17) . .
N2 C1 Cu1 128.53(15) . .
N5 C1 Cu1 125.11(14) . .
N2 C3 C4 101.35(16) . .
N2 C3 H3A 111.5 . .
C4 C3 H3A 111.5 . .
N2 C3 H3B 111.5 . .
C4 C3 H3B 111.5 . .
H3A C3 H3B 109.3 . .
N5 C4 C3 101.51(16) . .
N5 C4 H4A 111.5 . .
C3 C4 H4A 111.5 . .
N5 C4 H4B 111.5 . .
C3 C4 H4B 111.5 . .
H4A C4 H4B 109.3 . .
C7 C6 C11 121.49(19) . .
C7 C6 N2 119.89(19) . .
C11 C6 N2 118.18(19) . .
C6 C7 C8 118.2(2) . .
C6 C7 C12 121.80(19) . .
C8 C7 C12 120.0(2) . .
C9 C8 C7 122.0(2) . .
C9 C8 H8 119.0 . .
C7 C8 H8 119.0 . .
C10 C9 C8 118.0(2) . .
C10 C9 C13 121.3(2) . .
C8 C9 C13 120.7(2) . .
C9 C10 C11 122.6(2) . .
C9 C10 H10 118.7 . .
C11 C10 H10 118.7 . .
C6 C11 C10 117.6(2) . .
C6 C11 C14 122.37(19) . .
C10 C11 C14 120.0(2) . .
C7 C12 H12A 109.5 . .
C7 C12 H12B 109.5 . .
H12A C12 H12B 109.5 . .
C7 C12 H12C 109.5 . .
H12A C12 H12C 109.5 . .
H12B C12 H12C 109.5 . .
C9 C13 H13A 109.5 . .
C9 C13 H13B 109.5 . .
H13A C13 H13B 109.5 . .
C9 C13 H13C 109.5 . .
H13A C13 H13C 109.5 . .
H13B C13 H13C 109.5 . .
C11 C14 H14A 109.5 . .
C11 C14 H14B 109.5 . .
H14A C14 H14B 109.5 . .
C11 C14 H14C 109.5 . .
H14A C14 H14C 109.5 . .
H14B C14 H14C 109.5 . .
C16 C15 C20 121.44(19) . .
C16 C15 N5 120.5(2) . .
C20 C15 N5 117.87(19) . .
C15 C16 C17 118.3(2) . .
C15 C16 C21 121.4(2) . .
C17 C16 C21 120.3(2) . .
C18 C17 C16 121.9(2) . .
C18 C17 H17 119.0 . .
C16 C17 H17 119.0 . .
C19 C18 C17 118.3(2) . .
C19 C18 C22 121.2(3) . .
C17 C18 C22 120.4(3) . .
C18 C19 C20 122.3(2) . .
C18 C19 H19 118.9 . .
C20 C19 H19 118.9 . .
C19 C20 C15 117.8(2) . .
C19 C20 C23 120.4(2) . .
C15 C20 C23 121.8(2) . .
C16 C21 H21A 109.5 . .
C16 C21 H21B 109.5 . .
H21A C21 H21B 109.5 . .
C16 C21 H21C 109.5 . .
H21A C21 H21C 109.5 . .
H21B C21 H21C 109.5 . .
C18 C22 H22A 109.5 . .
C18 C22 H22B 109.5 . .
H22A C22 H22B 109.5 . .
C18 C22 H22C 109.5 . .
H22A C22 H22C 109.5 . .
H22B C22 H22C 109.5 . .
C20 C23 H23A 109.5 . .
C20 C23 H23B 109.5 . .
H23A C23 H23B 109.5 . .
C20 C23 H23C 109.5 . .
H23A C23 H23C 109.5 . .
H23B C23 H23C 109.5 . .
N32 C33 N34 114.7(2) . .
N32 C33 H33 122.6 . .
N34 C33 H33 122.6 . .
N31 C35 N34 114.9(2) . .
N31 C35 H35 122.6 . .
N34 C35 H35 122.6 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cu1 C1 1.900(2) .
Cu1 N32 1.9676(18) 3_556
Cu1 N31 1.9923(19) .
N2 C1 1.346(3) .
N2 C6 1.434(3) .
N2 C3 1.481(2) .
N5 C1 1.347(3) .
N5 C15 1.428(3) .
N5 C4 1.477(3) .
N31 C35 1.323(3) .
N31 N32 1.374(2) .
N32 C33 1.324(3) .
N32 Cu1 1.9676(18) 3_556
N34 C35 1.333(3) .
N34 C33 1.333(3) .
C3 C4 1.511(3) .
C3 H3A 0.9900 .
C3 H3B 0.9900 .
C4 H4A 0.9900 .
C4 H4B 0.9900 .
C6 C7 1.392(3) .
C6 C11 1.394(3) .
C7 C8 1.392(3) .
C7 C12 1.506(3) .
C8 C9 1.385(3) .
C8 H8 0.9500 .
C9 C10 1.376(4) .
C9 C13 1.508(3) .
C10 C11 1.395(3) .
C10 H10 0.9500 .
C11 C14 1.505(3) .
C12 H12A 0.9800 .
C12 H12B 0.9800 .
C12 H12C 0.9800 .
C13 H13A 0.9800 .
C13 H13B 0.9800 .
C13 H13C 0.9800 .
C14 H14A 0.9800 .
C14 H14B 0.9800 .
C14 H14C 0.9800 .
C15 C16 1.390(3) .
C15 C20 1.396(3) .
C16 C17 1.392(3) .
C16 C21 1.497(3) .
C17 C18 1.382(4) .
C17 H17 0.9500 .
C18 C19 1.378(4) .
C18 C22 1.511(3) .
C19 C20 1.394(3) .
C19 H19 0.9500 .
C20 C23 1.503(3) .
C21 H21A 0.9800 .
C21 H21B 0.9800 .
C21 H21C 0.9800 .
C22 H22A 0.9800 .
C22 H22B 0.9800 .
C22 H22C 0.9800 .
C23 H23A 0.9800 .
C23 H23B 0.9800 .
C23 H23C 0.9800 .
C33 H33 0.9500 .
C35 H35 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
C35 N31 N32 C33 -0.4(2) . .
Cu1 N31 N32 C33 169.20(16) . .
C35 N31 N32 Cu1 -176.77(16) . 3_556
Cu1 N31 N32 Cu1 -7.1(3) . 3_556
C6 N2 C1 N5 -165.64(19) . .
C3 N2 C1 N5 -6.5(2) . .
C6 N2 C1 Cu1 19.8(3) . .
C3 N2 C1 Cu1 178.96(16) . .
C15 N5 C1 N2 -179.6(2) . .
C4 N5 C1 N2 -7.9(2) . .
C15 N5 C1 Cu1 -4.8(3) . .
C4 N5 C1 Cu1 166.88(16) . .
C1 N2 C3 C4 17.2(2) . .
C6 N2 C3 C4 178.39(18) . .
C1 N5 C4 C3 18.1(2) . .
C15 N5 C4 C3 -169.52(19) . .
N2 C3 C4 N5 -19.2(2) . .
C1 N2 C6 C7 64.0(3) . .
C3 N2 C6 C7 -94.5(2) . .
C1 N2 C6 C11 -123.5(2) . .
C3 N2 C6 C11 78.1(2) . .
C11 C6 C7 C8 -0.4(3) . .
N2 C6 C7 C8 171.89(19) . .
C11 C6 C7 C12 -178.9(2) . .
N2 C6 C7 C12 -6.6(3) . .
C6 C7 C8 C9 -0.4(3) . .
C12 C7 C8 C9 178.1(2) . .
C7 C8 C9 C10 1.3(3) . .
C7 C8 C9 C13 -177.1(2) . .
C8 C9 C10 C11 -1.4(3) . .
C13 C9 C10 C11 176.9(2) . .
C7 C6 C11 C10 0.3(3) . .
N2 C6 C11 C10 -172.16(19) . .
C7 C6 C11 C14 178.8(2) . .
N2 C6 C11 C14 6.4(3) . .
C9 C10 C11 C6 0.7(3) . .
C9 C10 C11 C14 -177.9(2) . .
C1 N5 C15 C16 70.2(3) . .
C4 N5 C15 C16 -101.1(2) . .
C1 N5 C15 C20 -114.9(2) . .
C4 N5 C15 C20 73.8(3) . .
C20 C15 C16 C17 0.0(3) . .
N5 C15 C16 C17 174.69(19) . .
C20 C15 C16 C21 -176.8(2) . .
N5 C15 C16 C21 -2.1(3) . .
C15 C16 C17 C18 -0.8(3) . .
C21 C16 C17 C18 176.0(2) . .
C16 C17 C18 C19 0.7(3) . .
C16 C17 C18 C22 -178.9(2) . .
C17 C18 C19 C20 0.4(3) . .
C22 C18 C19 C20 180.0(2) . .
C18 C19 C20 C15 -1.2(3) . .
C18 C19 C20 C23 179.4(2) . .
C16 C15 C20 C19 1.0(3) . .
N5 C15 C20 C19 -173.84(18) . .
C16 C15 C20 C23 -179.6(2) . .
N5 C15 C20 C23 5.5(3) . .
N31 N32 C33 N34 0.3(3) . .
Cu1 N32 C33 N34 176.70(17) 3_556 .
C35 N34 C33 N32 -0.1(3) . .
N32 N31 C35 N34 0.4(3) . .
Cu1 N31 C35 N34 -169.06(17) . .
C33 N34 C35 N31 -0.2(3) . .
