#------------------------------------------------------------------------------
#$Date: 2016-03-21 13:13:48 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178694 $
#$URL: svn://www.crystallography.net/cod/cif/4/08/05/4080552.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_4080552
loop_
_publ_author_name
'Guernon, Hannah'
'Legault, Claude Y.'
_publ_section_title
;
 N-Acyliminoimidazolium Ylides as Precursors to AnionicN-Heterocyclic
 Carbene Ligands: Control of Topology and Reactivity
;
_journal_issue                   6
_journal_name_full               Organometallics
_journal_page_first              1988
_journal_paper_doi               10.1021/om400078f
_journal_volume                  32
_journal_year                    2013
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C52 H58 Ag2 N6 O2'
_chemical_formula_sum            'C46 H52 Ag2 N6 O2'
_chemical_formula_weight         936.7
_chemical_name_systematic
;
 ?
;
_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_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_creation_date             2012-09-07T10:09:56-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                101.011(4)
_cell_angle_beta                 109.771(4)
_cell_angle_gamma                98.455(5)
_cell_formula_units_Z            1
_cell_length_a                   10.3921(16)
_cell_length_b                   10.4385(16)
_cell_length_c                   11.1080(17)
_cell_measurement_reflns_used    7153
_cell_measurement_temperature    130(2)
_cell_measurement_theta_max      69.9481
_cell_measurement_theta_min      4.4333
_cell_measurement_wavelength     1.54186
_cell_volume                     1083.5(3)
_computing_cell_refinement       'SAINT V7.68A integration software'
_computing_data_collection       'Bruker APEX2 software'
_computing_data_reduction        'SORTAV (Blessing, 1995)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1986)'
_diffrn_ambient_temperature      130(2)
_diffrn_detector                 'APEX-II CCD'
_diffrn_measured_fraction_theta_full 0.924
_diffrn_measured_fraction_theta_max 0.915
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II'
_diffrn_measurement_method       'φ or ω oscillation scans'
_diffrn_orient_matrix_type       'x-axis to radiation source'
_diffrn_orient_matrix_UB_11      0.938868E-1
_diffrn_orient_matrix_UB_12      0.627538E-1
_diffrn_orient_matrix_UB_13      0.515995E-1
_diffrn_orient_matrix_UB_21      0.394557E-1
_diffrn_orient_matrix_UB_22      -0.479328E-1
_diffrn_orient_matrix_UB_23      -0.612028E-1
_diffrn_orient_matrix_UB_31      -0.257106E-1
_diffrn_orient_matrix_UB_32      0.617908E-1
_diffrn_orient_matrix_UB_33      -0.583408E-1
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54186
_diffrn_reflns_av_R_equivalents  0.0242
_diffrn_reflns_av_unetI/netI     0.0816
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5074
_diffrn_reflns_reduction_process
;
 Scaled and merged with Sortav
 R.H. Blessing, (1987) Cryst. Rev. 1, 3-58
 R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397
;
_diffrn_reflns_theta_full        70
_diffrn_reflns_theta_max         70.5
_diffrn_reflns_theta_min         4.43
_diffrn_source                   'sealed x-ray tube'
_exptl_absorpt_coefficient_mu    7.588
_exptl_absorpt_correction_T_max  0.753
_exptl_absorpt_correction_T_min  0.638
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 - Bruker AXS area detector scaling and absorption correction
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.436
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             480
_exptl_crystal_size_max          0.168
_exptl_crystal_size_mid          0.143
_exptl_crystal_size_min          0.14
_refine_diff_density_max         1.165
_refine_diff_density_min         -0.956
_refine_diff_density_rms         0.167
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     259
_refine_ls_number_reflns         3809
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0603
_refine_ls_R_factor_gt           0.0326
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0592P)²+0.9053P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0892
_refine_ls_wR_factor_ref         0.0998
_reflns_number_gt                3506
_reflns_number_total             3809
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            om400078f_si_002.cif
_cod_data_source_block           complex_3f
_cod_database_code               4080552
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
C18 C 0.3164(5) 0.0534(4) 0.8744(4) 0.0425(9) Uani 1 1 d .
H18 H 0.3215 -0.0377 0.8521 0.051 Uiso 1 1 calc R
C19 C 0.4378(4) 0.1523(5) 0.9353(4) 0.0403(9) Uani 1 1 d .
H19 H 0.5264 0.1294 0.954 0.048 Uiso 1 1 calc R
C20 C 0.4313(4) 0.2858(4) 0.9699(4) 0.0403(9) Uani 1 1 d .
H20 H 0.5152 0.3541 1.0133 0.048 Uiso 1 1 calc R
C21 C 0.3022(4) 0.3186(4) 0.9406(4) 0.0401(9) Uani 1 1 d .
H21 H 0.297 0.4096 0.9635 0.048 Uiso 1 1 calc R
C22 C 0.1790(4) 0.2176(4) 0.8773(4) 0.0402(9) Uani 1 1 d .
H22 H 0.0898 0.2395 0.8562 0.048 Uiso 1 1 calc R
C23 C 0.1884(4) 0.0856(4) 0.8455(4) 0.0409(9) Uani 1 1 d .
H23 H 0.1051 0.0165 0.8032 0.049 Uiso 1 1 calc R
C1 C 0.0046(4) 0.3829(4) 0.2542(4) 0.0370(9) Uani 1 1 d .
C2 C 0.1540(4) 0.4083(5) 0.2574(6) 0.0580(14) Uani 1 1 d .
H2A H 0.1849 0.3239 0.2505 0.087 Uiso 1 1 calc R
H2B H 0.2167 0.4727 0.3409 0.087 Uiso 1 1 calc R
H2C H 0.1566 0.4447 0.183 0.087 Uiso 1 1 calc R
C3 C -0.0042(7) 0.3028(7) 0.3537(5) 0.0770(18) Uani 1 1 d .
H3A H -0.0995 0.2879 0.3536 0.116 Uiso 1 1 calc R
H3B H 0.0628 0.3529 0.4424 0.116 Uiso 1 1 calc R
H3C H 0.0186 0.2163 0.329 0.116 Uiso 1 1 calc R
C4 C -0.0279(6) 0.5198(6) 0.2900(7) 0.085(2) Uani 1 1 d .
H4A H -0.0249 0.5675 0.2227 0.127 Uiso 1 1 calc R
H4B H 0.042 0.5721 0.3766 0.127 Uiso 1 1 calc R
H4C H -0.1217 0.5078 0.2936 0.127 Uiso 1 1 calc R
C5 C -0.1084(4) 0.3044(4) 0.1189(4) 0.0330(8) Uani 1 1 d .
C6 C -0.2543(4) 0.2330(4) -0.1670(4) 0.0333(8) Uani 1 1 d .
H6 H -0.2577 0.3244 -0.1421 0.04 Uiso 1 1 calc R
C7 C -0.3298(4) 0.1443(4) -0.2847(4) 0.0341(8) Uani 1 1 d .
H7 H -0.3974 0.1611 -0.3588 0.041 Uiso 1 1 calc R
C8 C 0.1920(3) -0.0365(3) 0.1560(3) 0.0255(7) Uani 1 1 d .
C9 C -0.3373(3) -0.0918(3) -0.3868(3) 0.0259(7) Uani 1 1 d .
C10 C -0.4389(4) -0.1991(3) -0.3934(3) 0.0273(7) Uani 1 1 d .
C11 C -0.4777(4) -0.3143(4) -0.4972(4) 0.0307(7) Uani 1 1 d .
C12 C -0.4191(4) -0.3219(4) -0.5935(3) 0.0303(7) Uani 1 1 d .
C13 C -0.3208(4) -0.2109(4) -0.5856(3) 0.0299(7) Uani 1 1 d .
C14 C -0.2788(3) -0.0940(4) -0.4838(3) 0.0311(7) Uani 1 1 d .
C15 C -0.5037(5) -0.1915(4) -0.2899(4) 0.0386(9) Uani 1 1 d .
H15A H -0.4359 -0.2006 -0.2075 0.058 Uiso 1 1 calc R
H15B H -0.5881 -0.2641 -0.3215 0.058 Uiso 1 1 calc R
H15C H -0.5292 -0.1049 -0.2735 0.058 Uiso 1 1 calc R
C16 C -0.4646(4) -0.4454(4) -0.7071(4) 0.0363(8) Uani 1 1 d .
H16A H -0.5165 -0.4243 -0.7898 0.054 Uiso 1 1 calc R
H16B H -0.5252 -0.5166 -0.6919 0.054 Uiso 1 1 calc R
H16C H -0.3816 -0.4756 -0.7134 0.054 Uiso 1 1 calc R
C17 C -0.1745(4) 0.0254(4) -0.4782(4) 0.0430(10) Uani 1 1 d .
H17A H -0.221 0.0994 -0.4923 0.064 Uiso 1 1 calc R
H17B H -0.1371 0.0016 -0.5473 0.064 Uiso 1 1 calc R
H17C H -0.0974 0.053 -0.3912 0.064 Uiso 1 1 calc R
Ag1 Ag 0.08861(2) 0.11089(2) 0.09927(2) 0.02540(11) Uani 1 1 d .
N1 N -0.2909(3) 0.0255(3) -0.2775(3) 0.0266(6) Uani 1 1 d .
N2 N -0.1713(3) 0.1651(3) -0.0901(3) 0.0254(6) Uani 1 1 d .
N3 N -0.0641(3) 0.2265(3) 0.0364(3) 0.0276(6) Uani 1 1 d .
O1 O -0.2296(3) 0.3177(4) 0.0937(3) 0.0585(10) 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 0.018 0.009 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ag Ag 0.131 4.282 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.031 0.018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.049 0.032 '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
C23 C18 C19 120.3(4) . .
C18 C19 C20 120.2(4) . .
C21 C20 C19 119.6(4) . .
C20 C21 C22 119.9(4) . .
C23 C22 C21 119.3(4) . .
C18 C23 C22 120.7(4) . .
C2 C1 C4 107.0(4) . .
C2 C1 C3 109.0(4) . .
C4 C1 C3 111.4(5) . .
C2 C1 C5 114.6(3) . .
C4 C1 C5 107.6(3) . .
C3 C1 C5 107.3(4) . .
O1 C5 N3 125.4(3) . .
O1 C5 C1 118.5(3) . .
N3 C5 C1 116.1(3) . .
C7 C6 N2 106.3(3) . .
C6 C7 N1 107.1(3) . .
N2 C8 N1 103.9(3) 2 2
N2 C8 Ag1 129.9(3) 2 .
N1 C8 Ag1 126.0(2) 2 .
C10 C9 C14 122.2(3) . .
C10 C9 N1 119.1(3) . .
C14 C9 N1 118.7(3) . .
C9 C10 C11 118.1(3) . .
C9 C10 C15 120.9(3) . .
C11 C10 C15 121.0(3) . .
C12 C11 C10 121.4(3) . .
C13 C12 C11 118.7(3) . .
C13 C12 C16 120.4(3) . .
C11 C12 C16 120.9(3) . .
C12 C13 C14 121.9(3) . .
C13 C14 C9 117.6(3) . .
C13 C14 C17 121.2(3) . .
C9 C14 C17 121.3(3) . .
C8 Ag1 N3 165.33(12) . .
C8 Ag1 Ag1 80.32(9) . 2
N3 Ag1 Ag1 89.64(7) . 2
C7 N1 C8 111.0(3) . 2
C7 N1 C9 124.7(3) . .
C8 N1 C9 124.0(3) 2 .
C8 N2 C6 111.7(3) 2 .
C8 N2 N3 123.6(3) 2 .
C6 N2 N3 124.2(3) . .
C5 N3 N2 113.0(3) . .
C5 N3 Ag1 124.1(3) . .
N2 N3 Ag1 114.19(19) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C18 C23 1.367(6) .
C18 C19 1.373(6) .
C19 C20 1.391(6) .
C20 C21 1.380(6) .
C21 C22 1.398(6) .
C22 C23 1.382(6) .
C1 C2 1.524(6) .
C1 C4 1.526(5) .
C1 C3 1.525(8) .
C1 C5 1.537(5) .
C5 O1 1.229(5) .
C5 N3 1.351(4) .
C6 C7 1.346(5) .
C6 N2 1.374(5) .
C7 N1 1.368(5) .
C8 N2 1.348(4) 2
C8 N1 1.364(5) 2
C8 Ag1 2.078(4) .
C9 C10 1.394(5) .
C9 C14 1.403(5) .
C9 N1 1.438(4) .
C10 C11 1.397(5) .
C10 C15 1.512(5) .
C11 C12 1.395(5) .
C12 C13 1.394(5) .
C12 C16 1.508(5) .
C13 C14 1.393(5) .
C14 C17 1.503(5) .
Ag1 N3 2.144(3) .
Ag1 Ag1 2.7682(5) 2
N1 C8 1.364(5) 2
N2 C8 1.348(4) 2
N2 N3 1.419(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
C23 C18 C19 C20 0.9(6) . .
C18 C19 C20 C21 -1.0(6) . .
C19 C20 C21 C22 0.3(6) . .
C20 C21 C22 C23 0.5(6) . .
C19 C18 C23 C22 -0.1(6) . .
C21 C22 C23 C18 -0.6(6) . .
C2 C1 C5 O1 -155.7(5) . .
C4 C1 C5 O1 -36.9(6) . .
C3 C1 C5 O1 83.0(5) . .
C2 C1 C5 N3 23.7(6) . .
C4 C1 C5 N3 142.5(5) . .
C3 C1 C5 N3 -97.6(5) . .
N2 C6 C7 N1 -0.4(4) . .
C14 C9 C10 C11 3.1(5) . .
N1 C9 C10 C11 -177.1(3) . .
C14 C9 C10 C15 -177.8(4) . .
N1 C9 C10 C15 2.0(5) . .
C9 C10 C11 C12 -1.3(5) . .
C15 C10 C11 C12 179.6(4) . .
C10 C11 C12 C13 -0.6(5) . .
C10 C11 C12 C16 -178.4(4) . .
C11 C12 C13 C14 0.8(6) . .
C16 C12 C13 C14 178.5(4) . .
C12 C13 C14 C9 1.0(5) . .
C12 C13 C14 C17 -179.0(4) . .
C10 C9 C14 C13 -3.0(5) . .
N1 C9 C14 C13 177.3(3) . .
C10 C9 C14 C17 177.0(4) . .
N1 C9 C14 C17 -2.8(5) . .
N2 C8 Ag1 N3 58.2(6) 2 .
N1 C8 Ag1 N3 -115.4(4) 2 .
N2 C8 Ag1 Ag1 10.8(3) 2 2
N1 C8 Ag1 Ag1 -162.8(3) 2 2
C6 C7 N1 C8 0.5(4) . 2
C6 C7 N1 C9 -173.8(3) . .
C10 C9 N1 C7 -104.4(4) . .
C14 C9 N1 C7 75.4(4) . .
C10 C9 N1 C8 82.1(4) . 2
C14 C9 N1 C8 -98.2(4) . 2
C7 C6 N2 C8 0.2(4) . 2
C7 C6 N2 N3 172.5(3) . .
O1 C5 N3 N2 3.9(6) . .
C1 C5 N3 N2 -175.5(3) . .
O1 C5 N3 Ag1 -141.7(4) . .
C1 C5 N3 Ag1 39.0(5) . .
C8 N2 N3 C5 -137.8(3) 2 .
C6 N2 N3 C5 50.8(5) . .
C8 N2 N3 Ag1 11.4(4) 2 .
C6 N2 N3 Ag1 -160.1(3) . .
C8 Ag1 N3 C5 84.4(5) . .
Ag1 Ag1 N3 C5 131.0(3) 2 .
C8 Ag1 N3 N2 -60.8(5) . .
Ag1 Ag1 N3 N2 -14.2(2) 2 .
