#------------------------------------------------------------------------------
#$Date: 2016-03-21 07:22:22 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178561 $
#$URL: svn://www.crystallography.net/cod/cif/4/06/69/4066951.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_4066951
loop_
_publ_author_name
'Fortman, George C.'
'Slawin, Alexandra M. Z.'
'Nolan, Steven P.'
_publ_section_title
;
 A Versatile Cuprous Synthon: [Cu(IPr)(OH)] (IPr = 1,3
 bis(diisopropylphenyl)imidazol-2-ylidene)
;
_journal_issue                   17
_journal_name_full               Organometallics
_journal_page_first              3966
_journal_paper_doi               10.1021/om100733n
_journal_volume                  29
_journal_year                    2010
_chemical_formula_moiety         'C29 H36 Cu F6 N3 O4 S2'
_chemical_formula_sum            'C29 H36 Cu F6 N3 O4 S2'
_chemical_formula_weight         732.27
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 112.500(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   16.188(6)
_cell_length_b                   10.971(3)
_cell_length_c                   19.954(7)
_cell_measurement_reflns_used    5564
_cell_measurement_temperature    93(2)
_cell_measurement_theta_max      28.6
_cell_measurement_theta_min      2.8
_cell_volume                     3274.0(19)
_computing_cell_refinement       'CrystalClear (Rigaku Corp., 2004)'
_computing_data_collection       'CrystalClear (Rigaku Corp., 2004)'
_computing_data_reduction        'CrystalClear (Rigaku Corp., 2004)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      93(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  CCD
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1219
_diffrn_reflns_av_sigmaI/netI    0.1270
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            9884
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_min         2.81
_exptl_absorpt_coefficient_mu    0.867
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.547
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.486
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             1512
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.708
_refine_diff_density_min         -0.708
_refine_diff_density_rms         0.141
_refine_ls_extinction_coef       0.0063(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     207
_refine_ls_number_reflns         2972
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0838
_refine_ls_R_factor_gt           0.0715
_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)+(0.1091P)²+2.7397P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1768
_refine_ls_wR_factor_ref         0.1882
_reflns_number_gt                2441
_reflns_number_total             2972
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om100733n_si_002.cif
_cod_data_source_block           11
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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_original_cell_volume        3274(2)
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               4066951
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
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 0.0000 1.02244(5) 0.2500 0.0316(3) Uani 1 2 d S
C1 C 0.0000 0.8530(5) 0.2500 0.0400(15) Uani 1 2 d S
N2 N 0.0495(3) 0.7760(3) 0.30434(16) 0.0428(9) Uani 1 1 d .
C3 C 0.0302(4) 0.6545(3) 0.2838(2) 0.0473(12) Uani 1 1 d .
H3A H 0.0555 0.5849 0.3126 0.057 Uiso 1 1 calc R
C4 C 0.1076(3) 0.8190(3) 0.3751(2) 0.0369(10) Uani 1 1 d .
C5 C 0.0722(3) 0.8152(3) 0.42934(18) 0.0311(8) Uani 1 1 d .
C6 C 0.1279(3) 0.8601(3) 0.49761(19) 0.0331(8) Uani 1 1 d .
H6A H 0.1073 0.8580 0.5362 0.040 Uiso 1 1 calc R
C7 C 0.2103(3) 0.9067(3) 0.5101(2) 0.0362(9) Uani 1 1 d .
H7A H 0.2459 0.9379 0.5567 0.043 Uiso 1 1 calc R
C8 C 0.2424(3) 0.9084(3) 0.4549(2) 0.0411(10) Uani 1 1 d .
H8A H 0.3003 0.9404 0.4643 0.049 Uiso 1 1 calc R
C9 C 0.1915(4) 0.8642(3) 0.3859(3) 0.0485(13) Uani 1 1 d .
C10 C -0.0195(3) 0.7670(4) 0.4167(2) 0.0441(10) Uani 1 1 d .
H10A H -0.0490 0.7465 0.3640 0.053 Uiso 1 1 calc R
C11 C -0.0137(3) 0.6496(4) 0.4594(3) 0.0513(11) Uani 1 1 d .
H11A H 0.0240 0.5905 0.4474 0.077 Uiso 1 1 calc R
H11B H -0.0737 0.6156 0.4467 0.077 Uiso 1 1 calc R
H11C H 0.0125 0.6674 0.5115 0.077 Uiso 1 1 calc R
C12 C -0.0778(3) 0.8624(5) 0.4336(3) 0.0604(13) Uani 1 1 d .
H12A H -0.0802 0.9365 0.4055 0.091 Uiso 1 1 calc R
H12B H -0.0522 0.8817 0.4855 0.091 Uiso 1 1 calc R
H12C H -0.1384 0.8300 0.4206 0.091 Uiso 1 1 calc R
C13 C 0.2280(7) 0.8662(5) 0.3262(4) 0.118(4) Uani 1 1 d .
H13A H 0.1687 0.8804 0.2860 0.141 Uiso 1 1 calc R
C14 C 0.2434(3) 0.7465(4) 0.2990(2) 0.0394(9) Uani 1 1 d .
H14A H 0.2629 0.7586 0.2587 0.059 Uiso 1 1 calc R
H14B H 0.1877 0.6994 0.2822 0.059 Uiso 1 1 calc R
H14C H 0.2896 0.7022 0.3382 0.059 Uiso 1 1 calc R
C15 C 0.2664(5) 0.9698(4) 0.3136(4) 0.086(2) Uani 1 1 d .
H15A H 0.2819 0.9579 0.2711 0.130 Uiso 1 1 calc R
H15B H 0.3208 0.9881 0.3560 0.130 Uiso 1 1 calc R
H15C H 0.2243 1.0378 0.3047 0.130 Uiso 1 1 calc R
N16 N 0.0000 1.1966(3) 0.2500 0.0282(9) Uani 1 2 d S
S17 S 0.00580(6) 1.26674(7) 0.32324(5) 0.0308(3) Uani 1 1 d .
O16 O -0.0222(2) 1.1819(2) 0.36474(15) 0.0403(7) Uani 1 1 d .
O17 O -0.0283(2) 1.3877(2) 0.31101(17) 0.0449(8) Uani 1 1 d .
C18 C 0.1267(3) 1.2837(3) 0.3748(2) 0.0359(9) Uani 1 1 d .
F1 F 0.16598(19) 1.1764(2) 0.38888(16) 0.0600(8) Uani 1 1 d .
F2 F 0.13990(19) 1.3391(2) 0.43685(14) 0.0551(7) Uani 1 1 d .
F3 F 0.16342(18) 1.3500(3) 0.33841(15) 0.0575(7) Uani 1 1 d .
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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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'
Cu Cu 0.3201 1.2651 '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
C1 Cu1 N16 180.000(1) . .
N2 C1 N2 103.6(4) 2 .
N2 C1 Cu1 128.2(2) 2 .
N2 C1 Cu1 128.2(2) . .
C1 N2 C3 111.1(4) . .
C1 N2 C4 122.6(3) . .
C3 N2 C4 126.1(3) . .
C3 C3 N2 107.1(2) 2 .
C3 C3 H3A 126.5 2 .
N2 C3 H3A 126.5 . .
C9 C4 C5 123.7(4) . .
C9 C4 N2 120.2(3) . .
C5 C4 N2 116.0(4) . .
C6 C5 C4 116.0(4) . .
C6 C5 C10 120.8(3) . .
C4 C5 C10 123.2(3) . .
C7 C6 C5 122.0(3) . .
C7 C6 H6A 119.0 . .
C5 C6 H6A 119.0 . .
C6 C7 C8 119.9(4) . .
C6 C7 H7A 120.0 . .
C8 C7 H7A 120.0 . .
C7 C8 C9 121.4(4) . .
C7 C8 H8A 119.3 . .
C9 C8 H8A 119.3 . .
C4 C9 C8 117.0(3) . .
C4 C9 C13 122.4(5) . .
C8 C9 C13 120.6(5) . .
C5 C10 C11 110.9(3) . .
C5 C10 C12 112.1(4) . .
C11 C10 C12 111.4(4) . .
C5 C10 H10A 107.4 . .
C11 C10 H10A 107.4 . .
C12 C10 H10A 107.4 . .
C10 C11 H11A 109.5 . .
C10 C11 H11B 109.5 . .
H11A C11 H11B 109.5 . .
C10 C11 H11C 109.5 . .
H11A C11 H11C 109.5 . .
H11B C11 H11C 109.5 . .
C10 C12 H12A 109.5 . .
C10 C12 H12B 109.5 . .
H12A C12 H12B 109.5 . .
C10 C12 H12C 109.5 . .
H12A C12 H12C 109.5 . .
H12B C12 H12C 109.5 . .
C15 C13 C14 121.4(4) . .
C15 C13 C9 119.9(5) . .
C14 C13 C9 116.4(4) . .
C15 C13 H13A 95.1 . .
C14 C13 H13A 95.1 . .
C9 C13 H13A 95.1 . .
C13 C14 H14A 109.5 . .
C13 C14 H14B 109.5 . .
H14A C14 H14B 109.5 . .
C13 C14 H14C 109.5 . .
H14A C14 H14C 109.5 . .
H14B C14 H14C 109.5 . .
C13 C15 H15A 109.5 . .
C13 C15 H15B 109.5 . .
H15A C15 H15B 109.5 . .
C13 C15 H15C 109.5 . .
H15A C15 H15C 109.5 . .
H15B C15 H15C 109.5 . .
S17 N16 S17 123.4(2) . 2
S17 N16 Cu1 118.30(12) . .
S17 N16 Cu1 118.30(12) 2 .
O17 S17 O16 121.25(18) . .
O17 S17 N16 113.76(18) . .
O16 S17 N16 106.95(16) . .
O17 S17 C18 105.14(18) . .
O16 S17 C18 104.32(18) . .
N16 S17 C18 103.55(12) . .
F1 C18 F3 109.1(3) . .
F1 C18 F2 108.6(3) . .
F3 C18 F2 108.5(3) . .
F1 C18 S17 110.6(3) . .
F3 C18 S17 110.8(3) . .
F2 C18 S17 109.1(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cu1 C1 1.859(5) .
Cu1 N16 1.911(4) .
C1 N2 1.366(4) 2
C1 N2 1.366(4) .
N2 C3 1.395(5) .
N2 C4 1.443(5) .
C3 C3 1.328(10) 2
C3 H3A 0.9500 .
C4 C9 1.384(7) .
C4 C5 1.406(5) .
C5 C6 1.404(5) .
C5 C10 1.503(6) .
C6 C7 1.360(6) .
C6 H6A 0.9500 .
C7 C8 1.386(5) .
C7 H7A 0.9500 .
C8 C9 1.393(7) .
C8 H8A 0.9500 .
C9 C13 1.520(5) .
C10 C11 1.527(7) .
C10 C12 1.531(6) .
C10 H10A 1.0000 .
C11 H11A 0.9800 .
C11 H11B 0.9800 .
C11 H11C 0.9800 .
C12 H12A 0.9800 .
C12 H12B 0.9800 .
C12 H12C 0.9800 .
C13 C15 1.364(7) .
C13 C14 1.477(6) .
C13 H13A 1.0000 .
C14 H14A 0.9800 .
C14 H14B 0.9800 .
C14 H14C 0.9800 .
C15 H15A 0.9800 .
C15 H15B 0.9800 .
C15 H15C 0.9800 .
N16 S17 1.622(2) .
N16 S17 1.622(2) 2
S17 O17 1.422(3) .
S17 O16 1.429(3) .
S17 C18 1.839(4) .
C18 F1 1.316(5) .
C18 F3 1.319(5) .
C18 F2 1.321(4) .
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
N2 C1 N2 C3 -0.4(2) 2 .
Cu1 C1 N2 C3 179.6(2) . .
N2 C1 N2 C4 -175.5(4) 2 .
Cu1 C1 N2 C4 4.5(4) . .
C1 N2 C3 C3 1.0(6) . 2
C4 N2 C3 C3 175.9(5) . 2
C1 N2 C4 C9 -80.0(5) . .
C3 N2 C4 C9 105.7(5) . .
C1 N2 C4 C5 98.0(4) . .
C3 N2 C4 C5 -76.4(5) . .
C9 C4 C5 C6 -0.4(5) . .
N2 C4 C5 C6 -178.3(3) . .
C9 C4 C5 C10 179.3(4) . .
N2 C4 C5 C10 1.4(5) . .
C4 C5 C6 C7 1.2(5) . .
C10 C5 C6 C7 -178.5(4) . .
C5 C6 C7 C8 -1.3(6) . .
C6 C7 C8 C9 0.6(6) . .
C5 C4 C9 C8 -0.3(5) . .
N2 C4 C9 C8 177.5(3) . .
C5 C4 C9 C13 179.6(4) . .
N2 C4 C9 C13 -2.6(6) . .
C7 C8 C9 C4 0.2(6) . .
C7 C8 C9 C13 -179.6(5) . .
C6 C5 C10 C11 -67.5(4) . .
C4 C5 C10 C11 112.8(4) . .
C6 C5 C10 C12 57.7(5) . .
C4 C5 C10 C12 -122.0(4) . .
C4 C9 C13 C15 132.3(8) . .
C8 C9 C13 C15 -47.8(11) . .
C4 C9 C13 C14 -64.8(9) . .
C8 C9 C13 C14 115.1(7) . .
S17 N16 S17 O17 22.91(14) 2 .
Cu1 N16 S17 O17 -157.10(14) . .
S17 N16 S17 O16 159.51(15) 2 .
Cu1 N16 S17 O16 -20.49(15) . .
S17 N16 S17 C18 -90.65(13) 2 .
Cu1 N16 S17 C18 89.34(13) . .
O17 S17 C18 F1 -179.4(3) . .
O16 S17 C18 F1 52.0(3) . .
N16 S17 C18 F1 -59.8(3) . .
O17 S17 C18 F3 -58.3(3) . .
O16 S17 C18 F3 173.2(3) . .
N16 S17 C18 F3 61.4(3) . .
O17 S17 C18 F2 61.1(3) . .
O16 S17 C18 F2 -67.5(3) . .
N16 S17 C18 F2 -179.2(3) . .
