#------------------------------------------------------------------------------
#$Date: 2016-03-26 03:00:22 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180164 $
#$URL: svn://www.crystallography.net/cod/cif/7/10/60/7106053.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_7106053
loop_
_publ_author_name
'Bin Liu'
'Yin Zhang'
'Daichao Xu'
'Wanzhi Chen'
_publ_section_title
;
 Facile Synthesis of Metal N-Heterocyclic Carbene Complexes
;
_journal_name_full               Chem.Commun.
_journal_page_first              2883
_journal_paper_doi               10.1039/c0cc05260d
_journal_volume                  47
_journal_year                    2011
_chemical_formula_sum            'C16 H16 Cu F12 N8 O2 P2'
_chemical_formula_weight         705.85
_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                101.646(2)
_cell_angle_beta                 106.212(2)
_cell_angle_gamma                98.9490(10)
_cell_formula_units_Z            1
_cell_length_a                   6.8197(6)
_cell_length_b                   8.5461(10)
_cell_length_c                   11.1542(13)
_cell_measurement_temperature    298(2)
_cell_volume                     595.66(11)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_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      298(2)
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0184
_diffrn_reflns_av_sigmaI/netI    0.0347
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            3078
_diffrn_reflns_theta_full        25.01
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_min         1.97
_exptl_absorpt_coefficient_mu    1.181
_exptl_absorpt_correction_T_max  0.7812
_exptl_absorpt_correction_T_min  0.6691
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   Sadabs
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.968
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             351
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.541
_refine_diff_density_min         -0.542
_refine_diff_density_rms         0.085
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     243
_refine_ls_number_reflns         2059
_refine_ls_number_restraints     12
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0519
_refine_ls_R_factor_gt           0.0421
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0689P)²+0.3710P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1083
_refine_ls_wR_factor_ref         0.1170
_reflns_number_gt                1732
_reflns_number_total             2059
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            C0CC05260D.TXT
_cod_data_source_block           080313e
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to the built-in table from CIF Core dictionary named
'cif_core.dic' version 2.4.1 from
2010-06-29.

'_exptl_absorpt_correction_type' value 'Multi-scan'
changed to 'multi-scan' according to the built-in table from CIF Core
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7106053
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
_atom_site_disorder_assembly
_atom_site_disorder_group
F6' F 0.797(4) 0.658(3) 0.3544(19) 0.083(5) Uani 0.50 1 d PD A 2
F1 F 0.847(3) 0.704(3) 0.3865(19) 0.091(6) Uani 0.50 1 d PD A 1
Cu1 Cu 1.0000 0.5000 0.5000 0.0355(2) Uani 1 2 d S . .
P1 P 0.81255(15) 0.77399(11) 0.26229(9) 0.0406(3) Uani 1 1 d D . .
F2 F 0.775(3) 0.843(2) 0.1382(12) 0.076(4) Uani 0.50 1 d PD A 1
F3 F 1.0399(17) 0.762(2) 0.2732(18) 0.099(6) Uani 0.50 1 d PD A 1
F4 F 0.738(2) 0.5972(10) 0.1733(13) 0.107(5) Uani 0.50 1 d PD A 1
F5 F 0.5798(16) 0.7827(15) 0.2464(16) 0.100(5) Uani 0.50 1 d PD A 1
F6 F 0.9013(13) 0.9563(10) 0.3467(9) 0.071(2) Uani 0.50 1 d PD A 1
F1' F 1.024(2) 0.732(2) 0.2450(16) 0.089(5) Uani 0.50 1 d PD A 2
F2' F 0.5968(17) 0.8029(17) 0.2751(13) 0.088(5) Uani 0.50 1 d PD A 2
F3' F 0.692(2) 0.6147(15) 0.1496(12) 0.112(5) Uani 0.50 1 d PD A 2
F4' F 0.833(3) 0.882(2) 0.1672(15) 0.098(6) Uani 0.50 1 d PD A 2
F5' F 0.911(3) 0.9183(16) 0.3763(13) 0.194(9) Uani 0.50 1 d PD A 2
N1 N 0.8034(4) 0.2689(3) 0.2074(3) 0.0366(6) Uani 1 1 d . . .
N2 N 1.0717(5) 0.3505(4) 0.1492(3) 0.0417(7) Uani 1 1 d . . .
N3 N 0.7396(4) 0.3148(3) 0.4071(3) 0.0358(6) Uani 1 1 d . . .
N4 N 0.4964(5) 0.1287(4) 0.2167(3) 0.0449(7) Uani 1 1 d . . .
O1 O 1.1141(4) 0.4303(3) 0.3664(2) 0.0410(6) Uani 1 1 d . . .
C1 C 1.0057(5) 0.3563(4) 0.2511(3) 0.0358(7) Uani 1 1 d . . .
C2 C 0.7444(7) 0.2078(5) 0.0720(3) 0.0498(10) Uani 1 1 d . . .
H2 H 0.6149 0.1442 0.0171 0.060 Uiso 1 1 calc R . .
C3 C 0.9103(7) 0.2590(5) 0.0389(4) 0.0520(10) Uani 1 1 d . . .
H3 H 0.9175 0.2372 -0.0447 0.062 Uiso 1 1 calc R . .
C4 C 0.6740(5) 0.2358(4) 0.2819(3) 0.0354(7) Uani 1 1 d . . .
C5 C 0.3717(6) 0.0905(5) 0.2841(4) 0.0497(9) Uani 1 1 d . . .
H5 H 0.2434 0.0167 0.2412 0.060 Uiso 1 1 calc R . .
C6 C 0.4255(6) 0.1566(5) 0.4155(4) 0.0503(10) Uani 1 1 d . . .
H6 H 0.3397 0.1257 0.4625 0.060 Uiso 1 1 calc R . .
C7 C 0.6098(6) 0.2686(5) 0.4727(4) 0.0459(9) Uani 1 1 d . . .
H7 H 0.6493 0.3161 0.5610 0.055 Uiso 1 1 calc R . .
C8 C 1.2736(6) 0.4414(5) 0.1539(4) 0.0527(10) Uani 1 1 d . . .
H8A H 1.2618 0.5486 0.1431 0.079 Uiso 1 1 calc R . .
H8B H 1.3167 0.3841 0.0859 0.079 Uiso 1 1 calc R . .
H8C H 1.3756 0.4517 0.2359 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'
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'
F F 0.0171 0.0103 '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'
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
_geom_angle_publ_flag
O1 Cu1 O1 180.000(1) 2_766 . ?
O1 Cu1 N3 89.73(10) 2_766 2_766 ?
O1 Cu1 N3 90.27(10) . 2_766 ?
O1 Cu1 N3 90.27(11) 2_766 . ?
O1 Cu1 N3 89.73(10) . . ?
N3 Cu1 N3 180.00(14) 2_766 . ?
F5' P1 F3 85.0(11) . . ?
F5' P1 F4 163.1(8) . . ?
F3 P1 F4 88.3(9) . . ?
F5' P1 F4' 91.5(10) . . ?
F3 P1 F4' 85.8(11) . . ?
F4 P1 F4' 103.4(9) . . ?
F5' P1 F5 96.9(10) . . ?
F3 P1 F5 178.0(9) . . ?
F4 P1 F5 90.1(7) . . ?
F4' P1 F5 93.6(10) . . ?
F5' P1 F2' 86.3(10) . . ?
F3 P1 F2' 170.6(9) . . ?
F4 P1 F2' 99.2(7) . . ?
F4' P1 F2' 97.9(10) . . ?
F5 P1 F2' 11.4(10) . . ?
F5' P1 F6 18.8(8) . . ?
F3 P1 F6 88.2(8) . . ?
F4 P1 F6 175.3(7) . . ?
F4' P1 F6 73.3(8) . . ?
F5 P1 F6 93.4(6) . . ?
F2' P1 F6 84.6(6) . . ?
F5' P1 F3' 173.8(8) . . ?
F3 P1 F3' 99.2(8) . . ?
F4 P1 F3' 15.3(9) . . ?
F4' P1 F3' 93.4(8) . . ?
F5 P1 F3' 79.0(7) . . ?
F2' P1 F3' 89.3(7) . . ?
F6 P1 F3' 164.3(7) . . ?
F5' P1 F6' 90.6(10) . . ?
F3 P1 F6' 92.1(11) . . ?
F4 P1 F6' 74.3(10) . . ?
F4' P1 F6' 176.9(13) . . ?
F5 P1 F6' 88.5(11) . . ?
F2' P1 F6' 84.6(10) . . ?
F6 P1 F6' 108.9(9) . . ?
F3' P1 F6' 84.8(10) . . ?
F5' P1 F2 106.6(9) . . ?
F3 P1 F2 95.0(11) . . ?
F4 P1 F2 89.3(9) . . ?
F4' P1 F2 17.1(12) . . ?
F5 P1 F2 83.9(10) . . ?
F2' P1 F2 90.8(10) . . ?
F6 P1 F2 87.9(8) . . ?
F3' P1 F2 77.7(8) . . ?
F6' P1 F2 161.9(10) . . ?
F5' P1 F1' 97.1(11) . . ?
F3 P1 F1' 12.2(12) . . ?
F4 P1 F1' 77.1(9) . . ?
F4' P1 F1' 83.7(11) . . ?
F5 P1 F1' 165.8(9) . . ?
F2' P1 F1' 176.3(9) . . ?
F6 P1 F1' 99.1(8) . . ?
F3' P1 F1' 87.3(8) . . ?
F6' P1 F1' 93.7(12) . . ?
F2 P1 F1' 89.9(11) . . ?
F5' P1 F1 73.8(10) . . ?
F3 P1 F1 85.7(10) . . ?
F4 P1 F1 90.3(10) . . ?
F4' P1 F1 163.6(11) . . ?
F5 P1 F1 95.4(10) . . ?
F2' P1 F1 88.6(9) . . ?
F6 P1 F1 92.5(9) . . ?
F3' P1 F1 101.8(10) . . ?
F6' P1 F1 17.5(15) . . ?
F2 P1 F1 179.2(10) . . ?
F1' P1 F1 90.7(10) . . ?
C1 N1 C4 127.2(3) . . ?
C1 N1 C2 108.4(3) . . ?
C4 N1 C2 124.3(3) . . ?
C1 N2 C3 109.0(3) . . ?
C1 N2 C8 124.2(3) . . ?
C3 N2 C8 126.4(3) . . ?
C4 N3 C7 114.2(3) . . ?
C4 N3 Cu1 126.1(2) . . ?
C7 N3 Cu1 119.6(2) . . ?
C4 N4 C5 116.2(3) . . ?
C1 O1 Cu1 124.3(2) . . ?
O1 C1 N2 125.2(3) . . ?
O1 C1 N1 127.4(3) . . ?
N2 C1 N1 107.4(3) . . ?
C3 C2 N1 106.3(3) . . ?
C3 C2 H2 126.9 . . ?
N1 C2 H2 126.9 . . ?
C2 C3 N2 108.9(3) . . ?
C2 C3 H3 125.5 . . ?
N2 C3 H3 125.5 . . ?
N4 C4 N3 127.4(3) . . ?
N4 C4 N1 114.2(3) . . ?
N3 C4 N1 118.4(3) . . ?
N4 C5 C6 122.4(4) . . ?
N4 C5 H5 118.8 . . ?
C6 C5 H5 118.8 . . ?
C7 C6 C5 116.6(4) . . ?
C7 C6 H6 121.7 . . ?
C5 C6 H6 121.7 . . ?
C6 C7 N3 123.1(3) . . ?
C6 C7 H7 118.4 . . ?
N3 C7 H7 118.4 . . ?
N2 C8 H8A 109.5 . . ?
N2 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
N2 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F6' P1 1.581(14) . ?
F1 P1 1.592(13) . ?
Cu1 O1 1.901(2) 2_766 ?
Cu1 O1 1.901(2) . ?
Cu1 N3 2.042(3) 2_766 ?
Cu1 N3 2.042(3) . ?
P1 F5' 1.490(12) . ?
P1 F3 1.543(10) . ?
P1 F4 1.549(8) . ?
P1 F4' 1.562(13) . ?
P1 F5 1.562(10) . ?
P1 F2' 1.569(8) . ?
P1 F6 1.574(8) . ?
P1 F3' 1.579(11) . ?
P1 F2 1.583(12) . ?
P1 F1' 1.590(11) . ?
N1 C1 1.363(4) . ?
N1 C4 1.406(4) . ?
N1 C2 1.411(4) . ?
N2 C1 1.329(4) . ?
N2 C3 1.387(5) . ?
N2 C8 1.453(5) . ?
N3 C4 1.335(4) . ?
N3 C7 1.358(4) . ?
N4 C4 1.315(4) . ?
N4 C5 1.329(5) . ?
O1 C1 1.263(4) . ?
C2 C3 1.324(6) . ?
C2 H2 0.9300 . ?
C3 H3 0.9300 . ?
C5 C6 1.380(6) . ?
C5 H5 0.9300 . ?
C6 C7 1.354(5) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 Cu1 N3 C4 158.9(3) 2_766 . . . ?
O1 Cu1 N3 C4 -21.1(3) . . . . ?
N3 Cu1 N3 C4 24(100) 2_766 . . . ?
O1 Cu1 N3 C7 -17.4(3) 2_766 . . . ?
O1 Cu1 N3 C7 162.6(3) . . . . ?
N3 Cu1 N3 C7 -153(100) 2_766 . . . ?
O1 Cu1 O1 C1 41(100) 2_766 . . . ?
N3 Cu1 O1 C1 -152.4(3) 2_766 . . . ?
N3 Cu1 O1 C1 27.6(3) . . . . ?
Cu1 O1 C1 N2 158.1(3) . . . . ?
Cu1 O1 C1 N1 -21.9(5) . . . . ?
C3 N2 C1 O1 -179.8(3) . . . . ?
C8 N2 C1 O1 -5.9(6) . . . . ?
C3 N2 C1 N1 0.2(4) . . . . ?
C8 N2 C1 N1 174.1(3) . . . . ?
C4 N1 C1 O1 -3.1(6) . . . . ?
C2 N1 C1 O1 179.8(3) . . . . ?
C4 N1 C1 N2 176.9(3) . . . . ?
C2 N1 C1 N2 -0.2(4) . . . . ?
C1 N1 C2 C3 0.2(4) . . . . ?
C4 N1 C2 C3 -177.1(3) . . . . ?
N1 C2 C3 N2 0.0(5) . . . . ?
C1 N2 C3 C2 -0.1(5) . . . . ?
C8 N2 C3 C2 -173.9(4) . . . . ?
C5 N4 C4 N3 -2.6(5) . . . . ?
C5 N4 C4 N1 178.3(3) . . . . ?
C7 N3 C4 N4 4.3(5) . . . . ?
Cu1 N3 C4 N4 -172.2(3) . . . . ?
C7 N3 C4 N1 -176.6(3) . . . . ?
Cu1 N3 C4 N1 6.8(4) . . . . ?
C1 N1 C4 N4 -170.5(3) . . . . ?
C2 N1 C4 N4 6.2(5) . . . . ?
C1 N1 C4 N3 10.3(5) . . . . ?
C2 N1 C4 N3 -173.0(3) . . . . ?
C4 N4 C5 C6 -1.1(6) . . . . ?
N4 C5 C6 C7 2.6(6) . . . . ?
C5 C6 C7 N3 -0.7(6) . . . . ?
C4 N3 C7 C6 -2.4(5) . . . . ?
Cu1 N3 C7 C6 174.4(3) . . . . ?
