#------------------------------------------------------------------------------
#$Date: 2016-03-21 06:51:35 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178537 $
#$URL: svn://www.crystallography.net/cod/cif/4/06/43/4064302.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_4064302
loop_
_publ_author_name
'Liu, Xianghao'
'Pattacini, Roberto'
'Deglmann, Peter'
'Braunstein, Pierre'
_publ_section_title
;
 Do Short C--H--M (M = Cu(I), Ag(I)) Distances Represent Agostic
 Interactions in Pincer-Type Complexes? Unusual NHC Transmetalation from
 Cu(I) to Ag(I)
;
_journal_issue                   12
_journal_name_full               Organometallics
_journal_page_first              3302
_journal_paper_doi               10.1021/om200033m
_journal_volume                  30
_journal_year                    2011
_chemical_formula_moiety         'C18 H22 Cu N4 , F6 P'
_chemical_formula_sum            'C18 H22 Cu F6 N4 P'
_chemical_formula_weight         502.91
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_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                69.90(1)
_cell_angle_beta                 81.25(2)
_cell_angle_gamma                79.82(2)
_cell_formula_units_Z            2
_cell_length_a                   8.553(2)
_cell_length_b                   11.092(3)
_cell_length_c                   11.628(3)
_cell_measurement_reflns_used    2504
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      26.373
_cell_measurement_theta_min      0.998
_cell_volume                     1014.7(5)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Bruker AXS BV, 1997-2004)'
_computing_data_reduction
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_molecular_graphics    ORTEP
_computing_publication_material  PLATON
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       CCD
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0338
_diffrn_reflns_av_sigmaI/netI    0.0714
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            5948
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.95
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    1.222
_exptl_absorpt_correction_T_max  0.901
_exptl_absorpt_correction_T_min  0.715
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'L. Spek, J. Appl.Cryst. 2003, 36, 7, B. Blessing, Acta Cryst, 1995, A51, 33'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.646
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.691
_refine_diff_density_min         -0.628
_refine_diff_density_rms         0.105
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     277
_refine_ls_number_reflns         3942
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0902
_refine_ls_R_factor_gt           0.0579
_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)+(0.0978P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1499
_refine_ls_wR_factor_ref         0.1653
_reflns_number_gt                2819
_reflns_number_total             3942
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om200033m_si_001.cif
_cod_data_source_block           CuL
_cod_database_code               4064302
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 0.42042(6) 0.18005(5) -0.00105(4) 0.0291(2) Uani 1 1 d .
C1 C 0.4195(5) 0.3095(4) -0.1609(4) 0.0272(9) Uani 1 1 d .
C2 C 0.3966(5) 0.0561(4) 0.1604(4) 0.0275(9) Uani 1 1 d .
C3 C 0.4944(6) 0.4595(4) -0.3402(4) 0.0338(10) Uani 1 1 d .
H3 H 0.5592 0.5120 -0.4052 0.041 Uiso 1 1 calc R
C4 C 0.3351(6) 0.4618(4) -0.3343(4) 0.0353(11) Uani 1 1 d .
H4 H 0.2664 0.5157 -0.3942 0.042 Uiso 1 1 calc R
C5 C 0.4522(6) -0.0914(5) 0.3455(4) 0.0359(11) Uani 1 1 d .
H5 H 0.5109 -0.1493 0.4104 0.043 Uiso 1 1 calc R
C6 C 0.2935(6) -0.0687(5) 0.3453(4) 0.0359(11) Uani 1 1 d .
H6 H 0.2179 -0.1068 0.4108 0.043 Uiso 1 1 calc R
C7 C 0.7137(5) 0.3310(4) -0.2110(3) 0.0295(10) Uani 1 1 d .
H7A H 0.7738 0.4043 -0.2579 0.035 Uiso 1 1 calc R
H7B H 0.7599 0.2564 -0.2392 0.035 Uiso 1 1 calc R
C8 C 0.7309(5) 0.2955(4) -0.0763(3) 0.0243(9) Uani 1 1 d .
C9 C 0.7289(5) 0.1670(4) -0.0045(4) 0.0272(9) Uani 1 1 d .
H9 H 0.7372 0.1039 -0.0442 0.033 Uiso 1 1 calc R
C10 C 0.7151(5) 0.1268(4) 0.1236(4) 0.0262(9) Uani 1 1 d .
C11 C 0.7097(5) 0.2188(4) 0.1824(3) 0.0264(9) Uani 1 1 d .
C12 C 0.7201(5) 0.3464(4) 0.1096(4) 0.0290(10) Uani 1 1 d .
H12 H 0.7233 0.4082 0.1487 0.035 Uiso 1 1 calc R
C13 C 0.7262(5) 0.3884(4) -0.0195(4) 0.0275(9) Uani 1 1 d .
C14 C 0.7220(6) 0.5303(4) -0.0903(4) 0.0375(11) Uani 1 1 d .
H14A H 0.8112 0.5433 -0.1552 0.056 Uiso 1 1 calc R
H14B H 0.7312 0.5772 -0.0345 0.056 Uiso 1 1 calc R
H14C H 0.6210 0.5632 -0.1275 0.056 Uiso 1 1 calc R
C15 C 0.6831(6) 0.1824(5) 0.3222(4) 0.0359(11) Uani 1 1 d .
H15A H 0.7142 0.2498 0.3475 0.054 Uiso 1 1 calc R
H15B H 0.7480 0.0995 0.3596 0.054 Uiso 1 1 calc R
H15C H 0.5701 0.1744 0.3494 0.054 Uiso 1 1 calc R
C16 C 0.6856(5) -0.0101(4) 0.1946(4) 0.0306(10) Uani 1 1 d .
H16A H 0.7236 -0.0657 0.1426 0.037 Uiso 1 1 calc R
H16B H 0.7458 -0.0436 0.2680 0.037 Uiso 1 1 calc R
C17 C 0.1269(5) 0.3482(5) -0.1819(4) 0.0391(11) Uani 1 1 d .
H17A H 0.1174 0.3045 -0.0926 0.059 Uiso 1 1 calc R
H17B H 0.0952 0.2937 -0.2228 0.059 Uiso 1 1 calc R
H17C H 0.0571 0.4313 -0.2013 0.059 Uiso 1 1 calc R
C18 C 0.0992(6) 0.0742(5) 0.1986(4) 0.0441(13) Uani 1 1 d .
H18A H 0.0240 0.0142 0.2475 0.066 Uiso 1 1 calc R
H18B H 0.0967 0.0879 0.1110 0.066 Uiso 1 1 calc R
H18C H 0.0690 0.1572 0.2140 0.066 Uiso 1 1 calc R
N1 N 0.5447(4) 0.3678(3) -0.2355(3) 0.0277(8) Uani 1 1 d .
N2 N 0.2922(4) 0.3707(4) -0.2248(3) 0.0297(8) Uani 1 1 d .
N3 N 0.5141(4) -0.0147(3) 0.2333(3) 0.0274(8) Uani 1 1 d .
N4 N 0.2599(4) 0.0197(3) 0.2334(3) 0.0284(8) Uani 1 1 d .
P1 P 0.09960(15) 0.27446(12) 0.46241(10) 0.0349(3) Uani 1 1 d .
F1 F 0.0223(6) 0.3019(5) 0.3403(4) 0.1088(16) Uani 1 1 d .
F2 F 0.2651(4) 0.2419(4) 0.3928(4) 0.1028(15) Uani 1 1 d .
F3 F 0.1225(5) 0.4227(3) 0.4178(3) 0.0790(11) Uani 1 1 d .
F4 F 0.1762(7) 0.2530(5) 0.5815(4) 0.132(2) Uani 1 1 d .
F5 F -0.0699(5) 0.3091(4) 0.5280(4) 0.0889(13) Uani 1 1 d .
F6 F 0.0743(5) 0.1278(3) 0.5055(4) 0.1016(15) 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
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0033 0.0016 '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'
P P 0.1023 0.0942 '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'
H H 0.0000 0.0000 '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
C2 Cu1 C1 173.74(17)
C2 Cu1 C9 94.24(16)
C1 Cu1 C9 91.80(15)
N2 C1 N1 103.1(3)
N2 C1 Cu1 127.9(3)
N1 C1 Cu1 128.9(3)
N3 C2 N4 102.8(3)
N3 C2 Cu1 127.8(3)
N4 C2 Cu1 129.3(3)
C4 C3 N1 107.2(4)
C4 C3 H3 126.4
N1 C3 H3 126.4
C3 C4 N2 106.4(4)
C3 C4 H4 126.8
N2 C4 H4 126.8
C6 C5 N3 106.6(4)
C6 C5 H5 126.7
N3 C5 H5 126.7
C5 C6 N4 107.4(4)
C5 C6 H6 126.3
N4 C6 H6 126.3
N1 C7 C8 111.2(3)
N1 C7 H7A 109.4
C8 C7 H7A 109.4
N1 C7 H7B 109.4
C8 C7 H7B 109.4
H7A C7 H7B 108.0
C9 C8 C13 119.4(4)
C9 C8 C7 117.7(4)
C13 C8 C7 122.4(4)
C8 C9 C10 122.5(4)
C8 C9 Cu1 93.6(2)
C10 C9 Cu1 90.3(2)
C8 C9 H9 118.8
C10 C9 H9 118.8
Cu1 C9 H9 86.0
C9 C10 C11 119.0(4)
C9 C10 C16 118.9(4)
C11 C10 C16 121.6(4)
C12 C11 C10 118.1(3)
C12 C11 C15 120.4(4)
C10 C11 C15 121.4(4)
C11 C12 C13 123.0(4)
C11 C12 H12 118.5
C13 C12 H12 118.5
C8 C13 C12 117.9(4)
C8 C13 C14 122.7(4)
C12 C13 C14 119.4(4)
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
C11 C15 H15A 109.5
C11 C15 H15B 109.5
H15A C15 H15B 109.5
C11 C15 H15C 109.5
H15A C15 H15C 109.5
H15B C15 H15C 109.5
N3 C16 C10 110.2(3)
N3 C16 H16A 109.6
C10 C16 H16A 109.6
N3 C16 H16B 109.6
C10 C16 H16B 109.6
H16A C16 H16B 108.1
N2 C17 H17A 109.5
N2 C17 H17B 109.5
H17A C17 H17B 109.5
N2 C17 H17C 109.5
H17A C17 H17C 109.5
H17B C17 H17C 109.5
N4 C18 H18A 109.5
N4 C18 H18B 109.5
H18A C18 H18B 109.5
N4 C18 H18C 109.5
H18A C18 H18C 109.5
H18B C18 H18C 109.5
C3 N1 C1 111.3(4)
C3 N1 C7 123.6(3)
C1 N1 C7 125.1(3)
C1 N2 C4 112.0(4)
C1 N2 C17 124.9(4)
C4 N2 C17 123.0(4)
C2 N3 C5 111.7(4)
C2 N3 C16 123.6(3)
C5 N3 C16 124.6(4)
C6 N4 C2 111.4(4)
C6 N4 C18 124.4(4)
C2 N4 C18 124.0(4)
F4 P1 F2 92.3(3)
F4 P1 F1 177.8(3)
F2 P1 F1 87.9(3)
F4 P1 F6 91.2(3)
F2 P1 F6 89.8(2)
F1 P1 F6 91.0(3)
F4 P1 F5 89.7(3)
F2 P1 F5 177.9(2)
F1 P1 F5 90.1(3)
F6 P1 F5 90.5(2)
F4 P1 F3 89.6(3)
F2 P1 F3 90.6(2)
F1 P1 F3 88.2(2)
F6 P1 F3 179.1(3)
F5 P1 F3 89.0(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cu1 C2 1.914(4)
Cu1 C1 1.919(4)
Cu1 C9 2.611(4)
C1 N2 1.355(5)
C1 N1 1.377(5)
C2 N3 1.367(5)
C2 N4 1.371(5)
C3 C4 1.349(6)
C3 N1 1.362(5)
C3 H3 0.9500
C4 N2 1.372(6)
C4 H4 0.9500
C5 C6 1.336(7)
C5 N3 1.375(5)
C5 H5 0.9500
C6 N4 1.369(6)
C6 H6 0.9500
C7 N1 1.474(5)
C7 C8 1.502(5)
C7 H7A 0.9900
C7 H7B 0.9900
C8 C9 1.383(6)
C8 C13 1.394(5)
C9 C10 1.393(5)
C9 H9 0.9500
C10 C11 1.402(5)
C10 C16 1.504(6)
C11 C12 1.388(6)
C11 C15 1.525(5)
C12 C13 1.407(5)
C12 H12 0.9500
C13 C14 1.502(6)
C14 H14A 0.9800
C14 H14B 0.9800
C14 H14C 0.9800
C15 H15A 0.9800
C15 H15B 0.9800
C15 H15C 0.9800
C16 N3 1.472(5)
C16 H16A 0.9900
C16 H16B 0.9900
C17 N2 1.461(6)
C17 H17A 0.9800
C17 H17B 0.9800
C17 H17C 0.9800
C18 N4 1.458(6)
C18 H18A 0.9800
C18 H18B 0.9800
C18 H18C 0.9800
P1 F4 1.549(4)
P1 F2 1.569(4)
P1 F1 1.570(4)
P1 F6 1.573(4)
P1 F5 1.580(3)
P1 F3 1.584(4)
