#------------------------------------------------------------------------------
#$Date: 2016-02-16 22:30:59 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176467 $
#$URL: svn://www.crystallography.net/cod/cif/4/08/05/4080550.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_4080550
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         'C17 H19 Ag1 Cl1 F3 N3 O1'
_chemical_formula_sum            'C17.5 H20 Ag Cl F3 N3 O'
_chemical_formula_weight         488.69
_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      2.3
_audit_creation_date             2013-01-15T15:02:00-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                91.22(4)
_cell_angle_beta                 109.88(4)
_cell_angle_gamma                107.34(3)
_cell_formula_units_Z            2
_cell_length_a                   8.529(4)
_cell_length_b                   10.391(3)
_cell_length_c                   12.512(7)
_cell_measurement_reflns_used    20
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      35
_cell_measurement_theta_min      30
_cell_measurement_wavelength     1.54176
_cell_volume                     986.1(9)
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      193(2)
_diffrn_measured_fraction_theta_full 0.96
_diffrn_measured_fraction_theta_max 0.958
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54176
_diffrn_reflns_av_R_equivalents  0
_diffrn_reflns_av_unetI/netI     0.0624
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            3595
_diffrn_reflns_theta_full        70
_diffrn_reflns_theta_max         70.11
_diffrn_reflns_theta_min         3.79
_exptl_absorpt_coefficient_mu    9.805
_exptl_absorpt_correction_T_max  0.2445
_exptl_absorpt_correction_T_min  0.111
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            tan
_exptl_crystal_density_diffrn    1.646
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             490
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         1.399
_refine_diff_density_min         -2.577
_refine_diff_density_rms         0.165
_refine_ls_extinction_coef       0.0095(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     243
_refine_ls_number_reflns         3595
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.14
_refine_ls_R_factor_gt           0.0947
_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)+(0.1898P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2494
_refine_ls_wR_factor_ref         0.285
_reflns_number_gt                2278
_reflns_number_total             3595
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om400078f_si_002.cif
_cod_data_source_block           complex_3b
_cod_original_cell_volume        986.1(7)
_cod_original_formula_sum        'C17.50 H20 Ag Cl F3 N3 O'
_cod_database_code               4080550
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
Cl1 Cl 0.6014(7) 0.0812(7) 0.4365(5) 0.126(3) Uani 0.944(15) 1 d PD
C20 C 0.444(4) -0.0837 0.430(3) 0.126(3) Uani 0.472(8) 1 d PD
H20A H 0.4944 -0.1569 0.4235 0.152 Uiso 0.472(8) 1 calc PR
H20B H 0.3346 -0.0999 0.3623 0.152 Uiso 0.472(8) 1 calc PR
C1 C 0.8120(17) 0.5829(16) 0.2196(11) 0.081(4) Uani 1 1 d .
C2 C 0.8240(18) 0.5666(16) 0.1139(11) 0.086(4) Uani 1 1 d .
H2 H 0.8903 0.5121 0.1027 0.103 Uiso 1 1 calc R
C3 C 0.742(2) 0.6272(17) 0.0224(12) 0.094(5) Uani 1 1 d .
H3 H 0.7546 0.6161 -0.0496 0.113 Uiso 1 1 calc R
C4 C 0.643(2) 0.7039(16) 0.0393(13) 0.090(4) Uani 1 1 d .
H4 H 0.5847 0.7439 -0.0231 0.107 Uiso 1 1 calc R
C5 C 0.6258(17) 0.7248(14) 0.1441(12) 0.080(3) Uani 1 1 d .
C6 C 0.7142(16) 0.6584(13) 0.2330(10) 0.069(3) Uani 1 1 d .
C7 C 0.8980(16) 0.5080(15) 0.3189(11) 0.078(3) Uani 1 1 d .
H7 H 0.8749 0.5351 0.3878 0.093 Uiso 1 1 calc R
C8 C 0.823(2) 0.3571(16) 0.2917(15) 0.112(6) Uani 1 1 d .
H8A H 0.8064 0.3298 0.212 0.169 Uiso 1 1 calc R
H8B H 0.7099 0.3257 0.3021 0.169 Uiso 1 1 calc R
H8C H 0.9051 0.3163 0.3432 0.169 Uiso 1 1 calc R
C9 C 1.097(2) 0.556(2) 0.3492(16) 0.119(6) Uani 1 1 d .
H9A H 1.1527 0.5167 0.4164 0.179 Uiso 1 1 calc R
H9B H 1.1434 0.6559 0.3666 0.179 Uiso 1 1 calc R
H9C H 1.1242 0.5278 0.2841 0.179 Uiso 1 1 calc R
C10 C 0.526(2) 0.8175(17) 0.1654(13) 0.089(4) Uani 1 1 d .
H10 H 0.526 0.8121 0.245 0.107 Uiso 1 1 calc R
C11 C 0.330(2) 0.765(2) 0.0804(15) 0.111(5) Uani 1 1 d .
H11A H 0.2783 0.8374 0.0766 0.166 Uiso 1 1 calc R
H11B H 0.2639 0.6867 0.1074 0.166 Uiso 1 1 calc R
H11C H 0.3264 0.7366 0.004 0.166 Uiso 1 1 calc R
C12 C 0.610(2) 0.9614(16) 0.1570(17) 0.111(6) Uani 1 1 d .
H12A H 0.6022 0.9708 0.0777 0.166 Uiso 1 1 calc R
H12B H 0.7341 0.9915 0.2079 0.166 Uiso 1 1 calc R
H12C H 0.5492 1.0174 0.1797 0.166 Uiso 1 1 calc R
C13 C 0.5604(13) 0.6043(12) 0.3744(10) 0.065(3) Uani 1 1 d .
H13 H 0.4645 0.5271 0.3299 0.078 Uiso 1 1 calc R
C14 C 0.5889(15) 0.6614(13) 0.4800(11) 0.072(3) Uani 1 1 d .
H14 H 0.5164 0.6326 0.524 0.087 Uiso 1 1 calc R
C15 C 0.8142(14) 0.7867(12) 0.4285(8) 0.060(3) Uani 1 1 d .
C16 C 1.1982(16) 1.1853(14) 0.2919(10) 0.072(3) Uani 1 1 d .
C17 C 1.127(2) 1.0833(19) 0.1858(12) 0.097(5) Uani 1 1 d .
Ag1 Ag 1.00900(11) 0.94110(10) 0.40278(8) 0.0721(5) Uani 1 1 d .
F1 F 1.0604(13) 0.9516(10) 0.1985(7) 0.108(3) Uani 1 1 d .
F2 F 1.0033(13) 1.1124(12) 0.1002(7) 0.118(3) Uani 1 1 d .
F3 F 1.2548(12) 1.0882(10) 0.1455(8) 0.105(3) Uani 1 1 d .
N1 N 0.6974(12) 0.6797(10) 0.3438(8) 0.066(2) Uani 1 1 d .
N2 N 0.7448(11) 0.7704(10) 0.5121(8) 0.063(2) Uani 1 1 d .
N3 N 1.1819(13) 1.1343(11) 0.3858(8) 0.069(2) Uani 1 1 d .
O1 O 1.2651(13) 1.3036(11) 0.2794(8) 0.093(3) 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 0.0181 0.0091 '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 0.1306 4.282 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
C20 Cl1 C20 73.3(13) . 2_656
Cl1 C20 Cl1 106.7(13) . 2_656
C6 C1 C2 117.8(14) . .
C6 C1 C7 121.0(12) . .
C2 C1 C7 121.0(13) . .
C1 C2 C3 122.4(15) . .
C4 C3 C2 118.1(14) . .
C3 C4 C5 122.5(15) . .
C4 C5 C6 115.4(14) . .
C4 C5 C10 122.6(14) . .
C6 C5 C10 122.0(13) . .
C1 C6 C5 123.8(12) . .
C1 C6 N1 120.2(11) . .
C5 C6 N1 116.0(11) . .
C8 C7 C9 111.0(14) . .
C8 C7 C1 113.2(11) . .
C9 C7 C1 109.3(13) . .
C12 C10 C5 112.8(14) . .
C12 C10 C11 110.5(13) . .
C5 C10 C11 109.9(13) . .
C14 C13 N1 106.6(10) . .
C13 C14 N2 106.8(10) . .
N2 C15 N1 102.7(9) . .
N2 C15 Ag1 133.4(8) . .
N1 C15 Ag1 122.9(7) . .
O1 C16 N3 129.5(12) . .
O1 C16 C17 115.0(12) . .
N3 C16 C17 115.5(12) . .
F3 C17 F2 104.8(11) . .
F3 C17 F1 105.7(14) . .
F2 C17 F1 107.6(14) . .
F3 C17 C16 109.9(13) . .
F2 C17 C16 111.9(15) . .
F1 C17 C16 116.2(11) . .
C15 Ag1 N3 166.3(4) . .
C15 Ag1 Ag1 79.2(3) . 2_776
N3 Ag1 Ag1 90.6(3) . 2_776
C13 N1 C15 111.7(10) . .
C13 N1 C6 125.2(10) . .
C15 N1 C6 122.9(9) . .
C15 N2 C14 112.1(10) . .
C15 N2 N3 121.8(9) . 2_776
C14 N2 N3 125.8(9) . 2_776
C16 N3 N2 115.9(10) . 2_776
C16 N3 Ag1 129.9(8) . .
N2 N3 Ag1 112.4(6) 2_776 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cl1 C20 1.813(12) .
Cl1 C20 1.84(4) 2_656
C20 Cl1 1.84(4) 2_656
C1 C6 1.349(19) .
C1 C2 1.371(18) .
C1 C7 1.565(19) .
C2 C3 1.39(2) .
C3 C4 1.38(2) .
C4 C5 1.39(2) .
C5 C6 1.433(19) .
C5 C10 1.53(2) .
C6 N1 1.459(16) .
C7 C8 1.49(2) .
C7 C9 1.528(18) .
C10 C12 1.48(2) .
C10 C11 1.56(2) .
C13 C14 1.349(18) .
C13 N1 1.379(13) .
C14 N2 1.390(14) .
C15 N2 1.357(13) .
C15 N1 1.387(14) .
C15 Ag1 2.058(11) .
C16 O1 1.229(15) .
C16 N3 1.332(15) .
C16 C17 1.504(19) .
C17 F3 1.336(16) .
C17 F2 1.337(18) .
C17 F1 1.352(18) .
Ag1 N3 2.172(10) .
Ag1 Ag1 2.771(2) 2_776
N2 N3 1.428(14) 2_776
N3 N2 1.428(14) 2_776
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
C20 Cl1 C20 Cl1 0 2_656 2_656
C6 C1 C2 C3 1(2) . .
C7 C1 C2 C3 177.1(13) . .
C1 C2 C3 C4 -1(2) . .
C2 C3 C4 C5 1(2) . .
C3 C4 C5 C6 -2(2) . .
C3 C4 C5 C10 175.8(14) . .
C2 C1 C6 C5 -1(2) . .
C7 C1 C6 C5 -177.3(12) . .
C2 C1 C6 N1 -179.7(12) . .
C7 C1 C6 N1 5(2) . .
C4 C5 C6 C1 2(2) . .
C10 C5 C6 C1 -175.8(14) . .
C4 C5 C6 N1 179.9(12) . .
C10 C5 C6 N1 2.5(18) . .
C6 C1 C7 C8 113.9(16) . .
C2 C1 C7 C8 -61.8(19) . .
C6 C1 C7 C9 -121.9(15) . .
C2 C1 C7 C9 62.5(18) . .
C4 C5 C10 C12 -64.2(19) . .
C6 C5 C10 C12 113.0(16) . .
C4 C5 C10 C11 60(2) . .
C6 C5 C10 C11 -123.2(15) . .
N1 C13 C14 N2 -0.6(13) . .
O1 C16 C17 F3 57.1(19) . .
N3 C16 C17 F3 -122.1(14) . .
O1 C16 C17 F2 -59.0(17) . .
N3 C16 C17 F2 121.9(14) . .
O1 C16 C17 F1 176.9(13) . .
N3 C16 C17 F1 -2(2) . .
N2 C15 Ag1 N3 -47(2) . .
N1 C15 Ag1 N3 120.1(15) . .
N2 C15 Ag1 Ag1 -4.8(11) . 2_776
N1 C15 Ag1 Ag1 162.1(10) . 2_776
C14 C13 N1 C15 -0.6(14) . .
C14 C13 N1 C6 -176.3(11) . .
N2 C15 N1 C13 1.6(13) . .
Ag1 C15 N1 C13 -168.6(8) . .
N2 C15 N1 C6 177.4(10) . .
Ag1 C15 N1 C6 7.1(16) . .
C1 C6 N1 C13 -95.9(15) . .
C5 C6 N1 C13 85.7(15) . .
C1 C6 N1 C15 88.9(16) . .
C5 C6 N1 C15 -89.5(14) . .
N1 C15 N2 C14 -1.9(13) . .
Ag1 C15 N2 C14 166.8(9) . .
N1 C15 N2 N3 -175.7(9) . 2_776
Ag1 C15 N2 N3 -7.0(18) . 2_776
C13 C14 N2 C15 1.6(14) . .
C13 C14 N2 N3 175.1(10) . 2_776
O1 C16 N3 N2 -1(2) . 2_776
C17 C16 N3 N2 177.7(11) . 2_776
O1 C16 N3 Ag1 161.9(11) . .
C17 C16 N3 Ag1 -19.1(18) . .
C15 Ag1 N3 C16 -107.1(18) . .
Ag1 Ag1 N3 C16 -148.2(11) 2_776 .
C15 Ag1 N3 N2 56.6(18) . 2_776
Ag1 Ag1 N3 N2 15.6(7) 2_776 2_776
