#------------------------------------------------------------------------------
#$Date: 2016-03-26 03:23:13 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180180 $
#$URL: svn://www.crystallography.net/cod/cif/7/10/76/7107651.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_7107651
loop_
_publ_author_name
'Benjamin R. M. Lake'
'Emma K. Bullough'
'Thomas J. Williams'
'Adrian C. Whitwood'
'Marc A. Little'
'Charlotte E. Willans'
_publ_section_title
;
 Simple and versatile selective synthesis of neutral and cationic
 copper(I) N-heterocyclic carbene complexes using an electrochemical
 procedure
;
_journal_name_full               Chem.Commun.
_journal_page_first              4887
_journal_paper_doi               10.1039/c2cc30862b
_journal_volume                  48
_journal_year                    2012
_chemical_formula_moiety         'C44 H40 Cu2 N8, 2(F6 P)'
_chemical_formula_sum            'C44 H40 Cu2 F12 N8 P2'
_chemical_formula_weight         1097.88
_chemical_name_systematic
;
?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_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_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 92.910(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.7429(13)
_cell_length_b                   11.0137(17)
_cell_length_c                   23.226(4)
_cell_measurement_reflns_used    7576
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      28.366
_cell_measurement_theta_min      2.548
_cell_volume                     2233.6(6)
_computing_cell_refinement
;
APEX 2 software, Bruker Nonius 2004
;
_computing_data_collection
;
APEX 2 software, Bruker Nonius 2004
;
_computing_data_reduction
;
SAINT - Bruker Integration program embedded in
APEX 2 software, Bruker Nonius 2004
;
_computing_molecular_graphics    'ORTEP-III Version 1.08 (Farrugia, 2005)'
_computing_publication_material
;
enCIFer: A program for viewing, editing and visualising CIFs.
F. H. Allen, O. Johnson, G. P. Shields, B. R. Smith, M. Towler,
J. Applied Cryst., 37, 331-334, 2004
;
_computing_structure_refinement
;
SHELXS-97 (Sheldrick, G. M. Acta Cryst. (2008). A64, 112)
XSeed (L.J.Barbour, J.Supramol. Chem., 2003, 1, 189.)
;
_computing_structure_solution
;
SHELXS-97 (Sheldrick, G. M. Acta Cryst. (2008). A64, 112)
XSeed (L.J.Barbour, J.Supramol. Chem., 2003, 1, 189.)
;
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean
;
120 microns
;
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'ApexII camera'
_diffrn_measurement_method       'rotation images'
_diffrn_radiation_monochromator
;
Mach3 kappa-type 4-circle goniostat.
;
_diffrn_radiation_source
;
Bruker Nonius FR591 rotating anode generator
;
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0332
_diffrn_reflns_av_sigmaI/netI    0.0197
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            38495
_diffrn_reflns_theta_full        28.38
_diffrn_reflns_theta_max         28.38
_diffrn_reflns_theta_min         2.05
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.118
_exptl_absorpt_correction_T_max  0.8592
_exptl_absorpt_correction_T_min  0.6696
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
See Sheldrick, G. M. (2002). SADABS.
University of Gottingen, Germany.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.632
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1112
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.360
_refine_diff_density_min         -0.302
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     307
_refine_ls_number_reflns         5563
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.099
_refine_ls_R_factor_all          0.0345
_refine_ls_R_factor_gt           0.0298
_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)+(0.0265P)²+2.2380P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0775
_refine_ls_wR_factor_ref         0.0799
_reflns_number_gt                4989
_reflns_number_total             5563
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2cc30862b.txt
_cod_data_source_block           brml95
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7107651
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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 0.29745(2) 0.52798(2) 0.005293(9) 0.02099(7) Uani 1 1 d .
N3 N 0.28486(16) 0.48011(14) 0.12903(6) 0.0195(3) Uani 1 1 d .
N4 N 0.31431(16) 0.31651(13) 0.08179(6) 0.0189(3) Uani 1 1 d .
N2 N 0.30111(16) 0.57114(14) -0.11874(6) 0.0191(3) Uani 1 1 d .
C12 C 0.29887(18) 0.43813(16) 0.07491(7) 0.0184(3) Uani 1 1 d .
C1 C 0.29077(18) 0.61606(16) -0.06496(7) 0.0186(3) Uani 1 1 d .
C7 C -0.1062(2) 0.37619(16) -0.16985(7) 0.0216(3) Uani 1 1 d .
N1 N 0.27038(16) 0.73686(13) -0.07315(6) 0.0203(3) Uani 1 1 d .
C3 C 0.2863(2) 0.66143(18) -0.15957(8) 0.0273(4) Uani 1 1 d .
H3 H 0.2890 0.6516 -0.2001 0.033 Uiso 1 1 calc R
C4 C 0.3128(2) 0.44215(17) -0.13354(8) 0.0239(4) Uani 1 1 d .
H4A H 0.3313 0.3940 -0.0979 0.029 Uiso 1 1 calc R
H4B H 0.4009 0.4298 -0.1581 0.029 Uiso 1 1 calc R
C11 C 0.2550(2) 0.82536(17) -0.02711(9) 0.0269(4) Uani 1 1 d .
H11A H 0.2745 0.9073 -0.0427 0.032 Uiso 1 1 calc R
H11B H 0.3351 0.8089 0.0036 0.032 Uiso 1 1 calc R
C5 C 0.16846(19) 0.39848(16) -0.16510(7) 0.0206(3) Uani 1 1 d .
C15 C 0.3259(2) 0.23136(17) 0.03410(8) 0.0223(3) Uani 1 1 d .
H15A H 0.3737 0.1554 0.0491 0.027 Uiso 1 1 calc R
H15B H 0.3945 0.2664 0.0058 0.027 Uiso 1 1 calc R
C21 C 0.0344(2) 0.20982(16) 0.02959(7) 0.0205(3) Uani 1 1 d .
H21 H 0.0314 0.2410 0.0677 0.025 Uiso 1 1 calc R
C16 C 0.17396(19) 0.20046(15) 0.00330(7) 0.0196(3) Uani 1 1 d .
C6 C 0.0278(2) 0.41262(17) -0.14071(7) 0.0223(3) Uani 1 1 d .
H6 H 0.0236 0.4478 -0.1035 0.027 Uiso 1 1 calc R
C13 C 0.2909(2) 0.38689(18) 0.16882(8) 0.0252(4) Uani 1 1 d .
H13 H 0.2834 0.3942 0.2093 0.030 Uiso 1 1 calc R
C2 C 0.2672(2) 0.76601(18) -0.13119(8) 0.0273(4) Uani 1 1 d .
H2 H 0.2542 0.8445 -0.1477 0.033 Uiso 1 1 calc R
C14 C 0.3094(2) 0.28348(18) 0.13900(8) 0.0247(4) Uani 1 1 d .
H14 H 0.3175 0.2036 0.1543 0.030 Uiso 1 1 calc R
P1 P 0.50954(5) 0.42726(5) 0.32793(2) 0.02360(10) Uani 1 1 d .
F5 F 0.32744(13) 0.42481(13) 0.32594(6) 0.0384(3) Uani 1 1 d .
F4 F 0.51651(15) 0.32403(11) 0.37656(5) 0.0357(3) Uani 1 1 d .
F6 F 0.50146(18) 0.53133(14) 0.28005(6) 0.0534(4) Uani 1 1 d .
F1 F 0.5082(2) 0.52725(12) 0.37794(7) 0.0540(4) Uani 1 1 d .
F2 F 0.50994(17) 0.32600(14) 0.27900(6) 0.0486(4) Uani 1 1 d .
F3 F 0.69143(15) 0.43131(19) 0.32975(7) 0.0621(5) Uani 1 1 d .
C20 C -0.1005(2) 0.17361(16) 0.00015(8) 0.0219(3) Uani 1 1 d .
C22 C 0.2594(2) 0.60726(17) 0.14392(8) 0.0241(4) Uani 1 1 d .
H22A H 0.2637 0.6579 0.1088 0.029 Uiso 1 1 calc R
H22B H 0.3416 0.6347 0.1718 0.029 Uiso 1 1 calc R
C17 C 0.1773(2) 0.15684(17) -0.05268(8) 0.0254(4) Uani 1 1 d .
H17 H 0.2719 0.1514 -0.0709 0.030 Uiso 1 1 calc R
C18 C 0.0424(2) 0.12120(19) -0.08210(8) 0.0312(4) Uani 1 1 d .
H18 H 0.0448 0.0914 -0.1204 0.037 Uiso 1 1 calc R
C19 C -0.0951(2) 0.12909(18) -0.05568(8) 0.0282(4) Uani 1 1 d .
H19 H -0.1869 0.1039 -0.0758 0.034 Uiso 1 1 calc R
C10 C 0.1747(2) 0.3463(2) -0.21880(9) 0.0415(6) Uani 1 1 d .
H10 H 0.2705 0.3359 -0.2357 0.050 Uiso 1 1 calc R
C8 C -0.0990(2) 0.3248(3) -0.22366(10) 0.0470(7) Uani 1 1 d .
H8 H -0.1904 0.3000 -0.2442 0.056 Uiso 1 1 calc R
C9 C 0.0409(3) 0.3090(3) -0.24800(12) 0.0662(10) Uani 1 1 d .
H9 H 0.0452 0.2724 -0.2849 0.079 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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 '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
C12 Cu1 C1 178.45(7) . .
C12 N3 C13 111.48(15) . .
C12 N3 C22 124.75(15) . .
C13 N3 C22 123.71(15) . .
C12 N4 C14 111.49(15) . .
C12 N4 C15 123.80(15) . .
C14 N4 C15 124.63(15) . .
C1 N2 C3 111.36(15) . .
C1 N2 C4 125.47(15) . .
C3 N2 C4 122.96(15) . .
N3 C12 N4 103.99(14) . .
N3 C12 Cu1 128.19(13) . .
N4 C12 Cu1 127.82(13) . .
N2 C1 N1 104.14(14) . .
N2 C1 Cu1 127.42(13) . .
N1 C1 Cu1 128.41(13) . .
C8 C7 C6 119.12(17) . .
C8 C7 C22 119.71(16) . 3_565
C6 C7 C22 121.17(16) . 3_565
C1 N1 C2 111.13(15) . .
C1 N1 C11 124.74(15) . .
C2 N1 C11 124.13(16) . .
C2 C3 N2 106.97(16) . .
C2 C3 H3 126.5 . .
N2 C3 H3 126.5 . .
N2 C4 C5 110.89(14) . .
N2 C4 H4A 109.5 . .
C5 C4 H4A 109.5 . .
N2 C4 H4B 109.5 . .
C5 C4 H4B 109.5 . .
H4A C4 H4B 108.0 . .
N1 C11 C20 115.13(15) . 3_565
N1 C11 H11A 108.5 . .
C20 C11 H11A 108.5 3_565 .
N1 C11 H11B 108.5 . .
C20 C11 H11B 108.5 3_565 .
H11A C11 H11B 107.5 . .
C10 C5 C6 119.54(17) . .
C10 C5 C4 120.22(16) . .
C6 C5 C4 120.23(16) . .
N4 C15 C16 114.21(14) . .
N4 C15 H15A 108.7 . .
C16 C15 H15A 108.7 . .
N4 C15 H15B 108.7 . .
C16 C15 H15B 108.7 . .
H15A C15 H15B 107.6 . .
C20 C21 C16 120.12(16) . .
C20 C21 H21 119.9 . .
C16 C21 H21 119.9 . .
C17 C16 C21 119.70(16) . .
C17 C16 C15 117.44(15) . .
C21 C16 C15 122.81(15) . .
C7 C6 C5 120.93(16) . .
C7 C6 H6 119.5 . .
C5 C6 H6 119.5 . .
C14 C13 N3 106.62(15) . .
C14 C13 H13 126.7 . .
N3 C13 H13 126.7 . .
C3 C2 N1 106.40(16) . .
C3 C2 H2 126.8 . .
N1 C2 H2 126.8 . .
C13 C14 N4 106.41(16) . .
C13 C14 H14 126.8 . .
N4 C14 H14 126.8 . .
F3 P1 F5 179.35(10) . .
F3 P1 F2 90.01(9) . .
F5 P1 F2 90.33(8) . .
F3 P1 F6 90.41(8) . .
F5 P1 F6 89.04(8) . .
F2 P1 F6 90.43(9) . .
F3 P1 F1 90.31(10) . .
F5 P1 F1 89.35(8) . .
F2 P1 F1 178.96(9) . .
F6 P1 F1 90.56(9) . .
F3 P1 F4 89.94(8) . .
F5 P1 F4 90.60(7) . .
F2 P1 F4 90.27(8) . .
F6 P1 F4 179.22(9) . .
F1 P1 F4 88.74(7) . .
C19 C20 C21 119.50(17) . .
C19 C20 C11 117.40(16) . 3_565
C21 C20 C11 123.03(16) . 3_565
N3 C22 C7 111.07(14) . 3_565
N3 C22 H22A 109.4 . .
C7 C22 H22A 109.4 3_565 .
N3 C22 H22B 109.4 . .
C7 C22 H22B 109.4 3_565 .
H22A C22 H22B 108.0 . .
C16 C17 C18 120.08(17) . .
C16 C17 H17 120.0 . .
C18 C17 H17 120.0 . .
C19 C18 C17 120.03(18) . .
C19 C18 H18 120.0 . .
C17 C18 H18 120.0 . .
C18 C19 C20 120.55(18) . .
C18 C19 H19 119.7 . .
C20 C19 H19 119.7 . .
C5 C10 C9 119.75(19) . .
C5 C10 H10 120.1 . .
C9 C10 H10 120.1 . .
C7 C8 C9 120.33(19) . .
C7 C8 H8 119.8 . .
C9 C8 H8 119.8 . .
C10 C9 C8 120.3(2) . .
C10 C9 H9 119.8 . .
C8 C9 H9 119.8 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cu1 C12 1.8952(17) .
Cu1 C1 1.8966(17) .
N3 C12 1.351(2) .
N3 C13 1.381(2) .
N3 C22 1.462(2) .
N4 C12 1.355(2) .
N4 C14 1.380(2) .
N4 C15 1.459(2) .
N2 C1 1.351(2) .
N2 C3 1.376(2) .
N2 C4 1.467(2) .
C1 N1 1.355(2) .
C7 C8 1.376(3) .
C7 C6 1.383(2) .
C7 C22 1.507(2) 3_565
N1 C2 1.385(2) .
N1 C11 1.458(2) .
C3 C2 1.342(3) .
C3 H3 0.9500 .
C4 C5 1.506(2) .
C4 H4A 0.9900 .
C4 H4B 0.9900 .
C11 C20 1.518(2) 3_565
C11 H11A 0.9900 .
C11 H11B 0.9900 .
C5 C10 1.377(3) .
C5 C6 1.389(2) .
C15 C16 1.515(2) .
C15 H15A 0.9900 .
C15 H15B 0.9900 .
C21 C20 1.391(2) .
C21 C16 1.396(2) .
C21 H21 0.9500 .
C16 C17 1.388(2) .
C6 H6 0.9500 .
C13 C14 1.347(3) .
C13 H13 0.9500 .
C2 H2 0.9500 .
C14 H14 0.9500 .
P1 F3 1.5893(14) .
P1 F5 1.5907(13) .
P1 F2 1.5923(14) .
P1 F6 1.5960(14) .
P1 F1 1.6011(14) .
P1 F4 1.6017(12) .
C20 C19 1.389(3) .
C20 C11 1.518(2) 3_565
C22 C7 1.507(2) 3_565
C22 H22A 0.9900 .
C22 H22B 0.9900 .
C17 C18 1.389(3) .
C17 H17 0.9500 .
C18 C19 1.380(3) .
C18 H18 0.9500 .
C19 H19 0.9500 .
C10 C9 1.384(3) .
C10 H10 0.9500 .
C8 C9 1.384(3) .
C8 H8 0.9500 .
C9 H9 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
C13 N3 C12 N4 -0.19(18) . .
C22 N3 C12 N4 -177.55(14) . .
C13 N3 C12 Cu1 179.83(12) . .
C22 N3 C12 Cu1 2.5(2) . .
C14 N4 C12 N3 0.23(18) . .
C15 N4 C12 N3 177.01(14) . .
C14 N4 C12 Cu1 -179.79(12) . .
C15 N4 C12 Cu1 -3.0(2) . .
C3 N2 C1 N1 -0.50(18) . .
C4 N2 C1 N1 -175.36(14) . .
C3 N2 C1 Cu1 177.84(13) . .
C4 N2 C1 Cu1 3.0(2) . .
N2 C1 N1 C2 0.36(18) . .
Cu1 C1 N1 C2 -177.95(13) . .
N2 C1 N1 C11 -179.14(14) . .
Cu1 C1 N1 C11 2.5(2) . .
C1 N2 C3 C2 0.5(2) . .
C4 N2 C3 C2 175.47(16) . .
C1 N2 C4 C5 110.49(18) . .
C3 N2 C4 C5 -63.8(2) . .
C1 N1 C11 C20 -76.1(2) . 3_565
C2 N1 C11 C20 104.5(2) . 3_565
N2 C4 C5 C10 123.3(2) . .
N2 C4 C5 C6 -55.5(2) . .
C12 N4 C15 C16 -79.3(2) . .
C14 N4 C15 C16 97.11(19) . .
C20 C21 C16 C17 1.1(3) . .
C20 C21 C16 C15 -176.36(16) . .
N4 C15 C16 C17 158.00(16) . .
N4 C15 C16 C21 -24.5(2) . .
C8 C7 C6 C5 0.3(3) . .
C22 C7 C6 C5 -179.22(17) 3_565 .
C10 C5 C6 C7 -0.7(3) . .
C4 C5 C6 C7 178.12(17) . .
C12 N3 C13 C14 0.1(2) . .
C22 N3 C13 C14 177.48(15) . .
N2 C3 C2 N1 -0.2(2) . .
C1 N1 C2 C3 -0.1(2) . .
C11 N1 C2 C3 179.41(16) . .
N3 C13 C14 N4 0.06(19) . .
C12 N4 C14 C13 -0.2(2) . .
C15 N4 C14 C13 -176.93(15) . .
C16 C21 C20 C19 -0.5(3) . .
C16 C21 C20 C11 176.53(17) . 3_565
C12 N3 C22 C7 115.73(18) . 3_565
C13 N3 C22 C7 -61.3(2) . 3_565
C21 C16 C17 C18 -0.8(3) . .
C15 C16 C17 C18 176.76(17) . .
C16 C17 C18 C19 0.0(3) . .
C17 C18 C19 C20 0.6(3) . .
C21 C20 C19 C18 -0.3(3) . .
C11 C20 C19 C18 -177.56(18) 3_565 .
C6 C5 C10 C9 0.3(4) . .
C4 C5 C10 C9 -178.5(3) . .
C6 C7 C8 C9 0.5(4) . .
C22 C7 C8 C9 -180.0(3) 3_565 .
C5 C10 C9 C8 0.5(5) . .
C7 C8 C9 C10 -0.9(5) . .
