#------------------------------------------------------------------------------
#$Date: 2016-03-25 13:34:00 +0200 (Fri, 25 Mar 2016) $
#$Revision: 179851 $
#$URL: svn://www.crystallography.net/cod/cif/7/01/47/7014700.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_7014700
loop_
_publ_author_name
'Li, Yanbo'
'Chen, Xiaofeng'
'Song, Yin'
'Fang, Ling'
'Zou, Gang'
_publ_section_title
;
 Well-defined N-heterocyclic carbene silver halides of
 1-cyclohexyl-3-arylmethylimidazolylidenes: synthesis, structure and
 catalysis in A(3)-reaction of aldehydes, amines and alkynes.
;
_journal_issue                   9
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              2046
_journal_page_last               2052
_journal_paper_doi               10.1039/c0dt01074j
_journal_volume                  40
_journal_year                    2011
_chemical_formula_sum            'C20 H22 Ag Cl N2'
_chemical_formula_weight         433.72
_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                91.356(2)
_cell_angle_beta                 105.679(2)
_cell_angle_gamma                97.504(2)
_cell_formula_units_Z            2
_cell_length_a                   8.6763(10)
_cell_length_b                   9.2220(11)
_cell_length_c                   12.2495(15)
_cell_measurement_reflns_used    2755
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      55.295
_cell_measurement_theta_min      4.464
_cell_volume                     933.78(19)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_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      293(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  0.0257
_diffrn_reflns_av_sigmaI/netI    0.0299
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            4911
_diffrn_reflns_theta_full        25.49
_diffrn_reflns_theta_max         25.49
_diffrn_reflns_theta_min         2.23
_exptl_absorpt_coefficient_mu    1.225
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.44611
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.543
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             440
_exptl_crystal_size_max          0.450
_exptl_crystal_size_mid          0.382
_exptl_crystal_size_min          0.317
_refine_diff_density_max         1.219
_refine_diff_density_min         -1.813
_refine_diff_density_rms         0.140
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         3428
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.071
_refine_ls_R_factor_all          0.0868
_refine_ls_R_factor_gt           0.0773
_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)+(0.1296P)²+2.3398P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2171
_refine_ls_wR_factor_ref         0.2278
_reflns_number_gt                2885
_reflns_number_total             3428
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            C0DT01074J.TXT
_cod_data_source_block           cd29590
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1555 2011-01-17 13:19:09Z saulius 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7014700
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
Ag Ag 0.59947(9) 0.85085(6) 0.94275(6) 0.0692(3) Uani 1 1 d P . .
Cl1 Cl 0.5168(2) 1.06875(17) 0.85923(13) 0.0622(5) Uani 1 1 d . . .
N1 N 0.6697(7) 0.5270(6) 0.9395(5) 0.0623(14) Uani 1 1 d . . .
N2 N 0.8274(9) 0.6507(7) 1.0841(5) 0.0755(17) Uani 1 1 d . . .
C1 C 0.7054(10) 0.6625(8) 0.9892(6) 0.0673(18) Uani 1 1 d . . .
C2 C 0.7621(10) 0.4315(9) 0.9990(7) 0.0720(19) Uani 1 1 d . . .
H2 H 0.7576 0.3326 0.9796 0.086 Uiso 1 1 calc R . .
C3 C 0.8610(10) 0.5086(10) 1.0914(7) 0.080(2) Uani 1 1 d . . .
H3 H 0.9376 0.4730 1.1493 0.096 Uiso 1 1 calc R . .
C4 C 0.9010(16) 0.7739(13) 1.1690(8) 0.120(4) Uani 1 1 d D . .
H4 H 0.8142 0.8348 1.1488 0.144 Uiso 1 1 calc R . .
C5 C 0.8997(19) 0.7534(13) 1.2774(8) 0.124(5) Uani 1 1 d . . .
H5A H 0.9586 0.6725 1.3030 0.149 Uiso 1 1 calc R . .
H5B H 0.7886 0.7238 1.2782 0.149 Uiso 1 1 calc R . .
C6 C 0.9698(15) 0.8818(13) 1.3622(8) 0.108(3) Uani 1 1 d . . .
H6A H 0.8828 0.9356 1.3672 0.129 Uiso 1 1 calc R . .
H6B H 1.0123 0.8446 1.4361 0.129 Uiso 1 1 calc R . .
C7 C 1.096(2) 0.9822(17) 1.3381(12) 0.146(8) Uani 1 1 d D . .
H7A H 1.0919 1.0776 1.3717 0.181 Uiso 1 1 calc R . .
H7B H 1.1978 0.9522 1.3785 0.181 Uiso 1 1 calc R . .
C8 C 1.100(2) 1.0019(14) 1.2234(12) 0.144(6) Uani 1 1 d D . .
H8A H 1.2119 1.0284 1.2235 0.173 Uiso 1 1 calc R . .
H8B H 1.0438 1.0841 1.1966 0.173 Uiso 1 1 calc R . .
C9 C 1.0270(14) 0.8719(11) 1.1390(10) 0.106(4) Uani 1 1 d D . .
H9A H 0.9820 0.9077 1.0649 0.127 Uiso 1 1 calc R . .
H9B H 1.1124 0.8166 1.1330 0.127 Uiso 1 1 calc R . .
C10 C 0.5457(9) 0.4877(10) 0.8321(6) 0.0719(19) Uani 1 1 d . . .
H10A H 0.4761 0.5634 0.8173 0.086 Uiso 1 1 calc R . .
H10B H 0.4796 0.3971 0.8392 0.086 Uiso 1 1 calc R . .
C11 C 0.6125(9) 0.4689(8) 0.7328(6) 0.0621(16) Uani 1 1 d . . .
C12 C 0.5565(9) 0.3484(8) 0.6604(6) 0.0656(17) Uani 1 1 d . . .
H12 H 0.4813 0.2759 0.6757 0.079 Uiso 1 1 calc R . .
C13 C 0.6097(9) 0.3302(9) 0.5621(6) 0.0697(19) Uani 1 1 d . . .
C14 C 0.5508(14) 0.2036(13) 0.4862(8) 0.104(3) Uani 1 1 d . . .
H14 H 0.4749 0.1309 0.5004 0.125 Uiso 1 1 calc R . .
C15 C 0.6052(17) 0.1885(17) 0.3925(9) 0.118(4) Uani 1 1 d . . .
H15 H 0.5654 0.1061 0.3427 0.142 Uiso 1 1 calc R . .
C16 C 0.7193(18) 0.2952(17) 0.3714(8) 0.115(4) Uani 1 1 d . . .
H16 H 0.7560 0.2841 0.3074 0.138 Uiso 1 1 calc R . .
C17 C 0.7772(13) 0.4149(14) 0.4425(8) 0.098(3) Uani 1 1 d . . .
H17 H 0.8545 0.4851 0.4271 0.118 Uiso 1 1 calc R . .
C18 C 0.7243(10) 0.4370(9) 0.5397(7) 0.0731(19) Uani 1 1 d . . .
C19 C 0.7812(11) 0.5626(10) 0.6160(8) 0.083(2) Uani 1 1 d . . .
H19 H 0.8558 0.6365 0.6018 0.099 Uiso 1 1 calc R . .
C20 C 0.7271(10) 0.5762(8) 0.7107(7) 0.0730(19) Uani 1 1 d . . .
H20 H 0.7675 0.6582 0.7609 0.088 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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ag Ag -0.8971 1.1015 '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
C1 Ag Cl1 166.5(2) . . ?
C1 N1 C2 112.8(6) . . ?
C1 N1 C10 123.1(7) . . ?
C2 N1 C10 124.1(6) . . ?
C1 N2 C3 110.5(6) . . ?
C1 N2 C4 122.8(9) . . ?
C3 N2 C4 126.6(9) . . ?
N1 C1 N2 103.6(7) . . ?
N1 C1 Ag 130.3(6) . . ?
N2 C1 Ag 126.0(5) . . ?
C3 C2 N1 106.1(7) . . ?
C3 C2 H2 126.9 . . ?
N1 C2 H2 126.9 . . ?
C2 C3 N2 106.9(7) . . ?
C2 C3 H3 126.6 . . ?
N2 C3 H3 126.6 . . ?
C5 C4 C9 122.9(10) . . ?
C5 C4 N2 117.5(9) . . ?
C9 C4 N2 113.3(7) . . ?
C5 C4 H4 98.4 . . ?
C9 C4 H4 98.4 . . ?
N2 C4 H4 98.4 . . ?
C4 C5 C6 116.9(10) . . ?
C4 C5 H5A 108.1 . . ?
C6 C5 H5A 108.1 . . ?
C4 C5 H5B 108.1 . . ?
C6 C5 H5B 108.1 . . ?
H5A C5 H5B 107.3 . . ?
C7 C6 C5 115.8(10) . . ?
C7 C6 H6A 108.3 . . ?
C5 C6 H6A 108.3 . . ?
C7 C6 H6B 108.3 . . ?
C5 C6 H6B 108.3 . . ?
H6A C6 H6B 107.4 . . ?
C8 C7 C6 120.5(11) . . ?
C8 C7 H7A 107.2 . . ?
C6 C7 H7A 107.2 . . ?
C8 C7 H7B 107.2 . . ?
C6 C7 H7B 107.2 . . ?
H7A C7 H7B 106.8 . . ?
C7 C8 C9 116.5(10) . . ?
C7 C8 H8A 108.2 . . ?
C9 C8 H8A 108.2 . . ?
C7 C8 H8B 108.2 . . ?
C9 C8 H8B 108.2 . . ?
H8A C8 H8B 107.3 . . ?
C4 C9 C8 113.9(8) . . ?
C4 C9 H9A 108.8 . . ?
C8 C9 H9A 108.8 . . ?
C4 C9 H9B 108.8 . . ?
C8 C9 H9B 108.8 . . ?
H9A C9 H9B 107.7 . . ?
N1 C10 C11 113.7(6) . . ?
N1 C10 H10A 108.8 . . ?
C11 C10 H10A 108.8 . . ?
N1 C10 H10B 108.8 . . ?
C11 C10 H10B 108.8 . . ?
H10A C10 H10B 107.7 . . ?
C12 C11 C20 119.1(7) . . ?
C12 C11 C10 119.7(7) . . ?
C20 C11 C10 121.1(7) . . ?
C11 C12 C13 121.6(7) . . ?
C11 C12 H12 119.2 . . ?
C13 C12 H12 119.2 . . ?
C18 C13 C12 119.6(7) . . ?
C18 C13 C14 119.0(8) . . ?
C12 C13 C14 121.5(9) . . ?
C15 C14 C13 120.2(12) . . ?
C15 C14 H14 119.9 . . ?
C13 C14 H14 119.9 . . ?
C14 C15 C16 120.3(11) . . ?
C14 C15 H15 119.9 . . ?
C16 C15 H15 119.9 . . ?
C17 C16 C15 120.4(10) . . ?
C17 C16 H16 119.8 . . ?
C15 C16 H16 119.8 . . ?
C16 C17 C18 121.8(11) . . ?
C16 C17 H17 119.1 . . ?
C18 C17 H17 119.1 . . ?
C13 C18 C17 118.4(9) . . ?
C13 C18 C19 118.2(7) . . ?
C17 C18 C19 123.4(9) . . ?
C20 C19 C18 120.6(8) . . ?
C20 C19 H19 119.7 . . ?
C18 C19 H19 119.7 . . ?
C19 C20 C11 121.0(7) . . ?
C19 C20 H20 119.5 . . ?
C11 C20 H20 119.5 . . ?
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
Ag C1 2.090(8) . ?
Ag Cl1 2.3824(16) . ?
N1 C1 1.337(9) . ?
N1 C2 1.360(10) . ?
N1 C10 1.460(9) . ?
N2 C1 1.362(11) . ?
N2 C3 1.379(11) . ?
N2 C4 1.475(10) . ?
C2 C3 1.342(11) . ?
C2 H2 0.9300 . ?
C3 H3 0.9300 . ?
C4 C5 1.348(13) . ?
C4 C9 1.457(11) . ?
C4 H4 0.9800 . ?
C5 C6 1.504(14) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 C7 1.434(19) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.431(14) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.516(13) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.497(10) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.356(10) . ?
C11 C20 1.393(11) . ?
C12 C13 1.415(11) . ?
C12 H12 0.9300 . ?
C13 C18 1.392(12) . ?
C13 C14 1.423(12) . ?
C14 C15 1.365(17) . ?
C14 H14 0.9300 . ?
C15 C16 1.383(19) . ?
C15 H15 0.9300 . ?
C16 C17 1.343(17) . ?
C16 H16 0.9300 . ?
C17 C18 1.406(12) . ?
C17 H17 0.9300 . ?
C18 C19 1.418(12) . ?
C19 C20 1.373(12) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C15 H15 Cl1 0.93 2.79 3.673(10) 159.0 2_666
C12 H12 Cl1 0.93 2.96 3.636(8) 130.4 1_545
C8 H8A Cl1 0.97 3.03 3.855(16) 144.0 2_777
C2 H2 Cl1 0.93 3.05 3.814(8) 140.7 1_545
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
C2 N1 C1 N2 0.5(8) . . . . ?
C10 N1 C1 N2 -178.8(6) . . . . ?
C2 N1 C1 Ag -176.9(6) . . . . ?
C10 N1 C1 Ag 3.8(11) . . . . ?
C3 N2 C1 N1 -1.2(9) . . . . ?
C4 N2 C1 N1 -177.1(7) . . . . ?
C3 N2 C1 Ag 176.4(6) . . . . ?
C4 N2 C1 Ag 0.5(11) . . . . ?
Cl1 Ag C1 N1 -80.0(13) . . . . ?
Cl1 Ag C1 N2 103.1(9) . . . . ?
C1 N1 C2 C3 0.4(9) . . . . ?
C10 N1 C2 C3 179.6(7) . . . . ?
N1 C2 C3 N2 -1.1(9) . . . . ?
C1 N2 C3 C2 1.4(10) . . . . ?
C4 N2 C3 C2 177.2(8) . . . . ?
C1 N2 C4 C5 123.3(14) . . . . ?
C3 N2 C4 C5 -51.9(18) . . . . ?
C1 N2 C4 C9 -83.8(14) . . . . ?
C3 N2 C4 C9 101.0(13) . . . . ?
C9 C4 C5 C6 32(2) . . . . ?
N2 C4 C5 C6 -177.8(12) . . . . ?
C4 C5 C6 C7 -29(2) . . . . ?
C5 C6 C7 C8 29(2) . . . . ?
C6 C7 C8 C9 -29(3) . . . . ?
C5 C4 C9 C8 -31(2) . . . . ?
N2 C4 C9 C8 178.0(12) . . . . ?
C7 C8 C9 C4 27(2) . . . . ?
C1 N1 C10 C11 104.3(8) . . . . ?
C2 N1 C10 C11 -74.9(10) . . . . ?
N1 C10 C11 C12 131.7(7) . . . . ?
N1 C10 C11 C20 -50.9(10) . . . . ?
C20 C11 C12 C13 -1.0(11) . . . . ?
C10 C11 C12 C13 176.4(7) . . . . ?
C11 C12 C13 C18 1.1(11) . . . . ?
C11 C12 C13 C14 -180.0(8) . . . . ?
C18 C13 C14 C15 -0.6(14) . . . . ?
C12 C13 C14 C15 -179.5(9) . . . . ?
C13 C14 C15 C16 0.7(17) . . . . ?
C14 C15 C16 C17 -0.2(18) . . . . ?
C15 C16 C17 C18 -0.5(16) . . . . ?
C12 C13 C18 C17 178.9(8) . . . . ?
C14 C13 C18 C17 -0.1(12) . . . . ?
C12 C13 C18 C19 -1.3(11) . . . . ?
C14 C13 C18 C19 179.7(8) . . . . ?
C16 C17 C18 C13 0.6(14) . . . . ?
C16 C17 C18 C19 -179.2(9) . . . . ?
C13 C18 C19 C20 1.5(13) . . . . ?
C17 C18 C19 C20 -178.7(9) . . . . ?
C18 C19 C20 C11 -1.5(13) . . . . ?
C12 C11 C20 C19 1.3(12) . . . . ?
C10 C11 C20 C19 -176.2(8) . . . . ?
