#------------------------------------------------------------------------------
#$Date: 2016-03-25 13:32:58 +0200 (Fri, 25 Mar 2016) $
#$Revision: 179850 $
#$URL: svn://www.crystallography.net/cod/cif/7/01/46/7014699.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_7014699
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            'C32 H40 Ag2 Cl2 N4'
_chemical_formula_weight         767.32
_chemical_name_systematic
;
?
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 94.549(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.1326(10)
_cell_length_b                   16.0862(16)
_cell_length_c                   19.984(2)
_cell_measurement_reflns_used    3979
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      53.019
_cell_measurement_theta_min      4.762
_cell_volume                     3247.0(6)
_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 0.996
_diffrn_measured_fraction_theta_max 0.996
_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  0.0742
_diffrn_reflns_av_sigmaI/netI    0.0577
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            9413
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         2.04
_exptl_absorpt_coefficient_mu    1.398
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75715
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.570
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             1552
_exptl_crystal_size_max          0.498
_exptl_crystal_size_mid          0.427
_exptl_crystal_size_min          0.234
_refine_diff_density_max         1.577
_refine_diff_density_min         -0.850
_refine_diff_density_rms         0.093
_refine_ls_extinction_coef       0.0012(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         3523
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.099
_refine_ls_R_factor_all          0.0595
_refine_ls_R_factor_gt           0.0501
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0697P)²+2.5341P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1380
_refine_ls_wR_factor_ref         0.1442
_reflns_number_gt                2781
_reflns_number_total             3523
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            C0DT01074J.TXT
_cod_data_source_block           cd26330
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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      C2/c
_cod_database_code               7014699
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
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 0.86865(3) 0.24421(2) 0.716157(17) 0.06072(19) Uani 1 1 d . . .
Cl Cl 0.96083(13) 0.14506(7) 0.64882(6) 0.0744(4) Uani 1 1 d . . .
N1 N 0.7515(3) 0.3622(2) 0.82332(16) 0.0578(8) Uani 1 1 d . . .
N2 N 0.7481(3) 0.4159(2) 0.72566(17) 0.0604(9) Uani 1 1 d . . .
C1 C 0.7842(4) 0.3466(3) 0.7597(2) 0.0551(9) Uani 1 1 d . . .
C2 C 0.6959(5) 0.4738(3) 0.7662(2) 0.0712(12) Uani 1 1 d . . .
H2 H 0.6654 0.5265 0.7538 0.085 Uiso 1 1 calc R . .
C3 C 0.6974(4) 0.4399(3) 0.8271(2) 0.0701(12) Uani 1 1 d . . .
H3 H 0.6673 0.4645 0.8651 0.084 Uiso 1 1 calc R . .
C4 C 0.7648(4) 0.3022(3) 0.8780(2) 0.0654(11) Uani 1 1 d . . .
H4A H 0.8070 0.3289 0.9176 0.078 Uiso 1 1 calc R . .
H4B H 0.8215 0.2570 0.8657 0.078 Uiso 1 1 calc R . .
C5 C 0.6348(5) 0.2677(3) 0.8942(2) 0.0594(10) Uani 1 1 d . . .
C6 C 0.5580(5) 0.2217(3) 0.8463(2) 0.0693(12) Uani 1 1 d . . .
H6 H 0.5885 0.2131 0.8042 0.083 Uiso 1 1 calc R . .
C7 C 0.4387(5) 0.1892(4) 0.8603(3) 0.0839(15) Uani 1 1 d . . .
H7 H 0.3888 0.1584 0.8281 0.101 Uiso 1 1 calc R . .
C8 C 0.3928(5) 0.2026(4) 0.9231(3) 0.0893(17) Uani 1 1 d . . .
H8 H 0.3105 0.1819 0.9325 0.107 Uiso 1 1 calc R . .
C9 C 0.4671(7) 0.2456(3) 0.9709(3) 0.0877(19) Uani 1 1 d . . .
H9 H 0.4374 0.2525 1.0135 0.105 Uiso 1 1 calc R . .
C10 C 0.5865(5) 0.2790(4) 0.9562(2) 0.0704(12) Uani 1 1 d . . .
H10 H 0.6357 0.3097 0.9887 0.084 Uiso 1 1 calc R . .
C11 C 0.7724(4) 0.4274(3) 0.6544(2) 0.0602(10) Uani 1 1 d . . .
H11 H 0.7972 0.3725 0.6384 0.072 Uiso 1 1 calc R . .
C12 C 0.6532(5) 0.4504(5) 0.6132(3) 0.105(2) Uani 1 1 d . . .
H12A H 0.6167 0.5011 0.6306 0.126 Uiso 1 1 calc R . .
H12B H 0.5875 0.4068 0.6152 0.126 Uiso 1 1 calc R . .
C13 C 0.6839(7) 0.4641(7) 0.5398(3) 0.131(3) Uani 1 1 d . . .
H13A H 0.6998 0.4107 0.5193 0.157 Uiso 1 1 calc R . .
H13B H 0.6078 0.4893 0.5152 0.157 Uiso 1 1 calc R . .
C14 C 0.8003(12) 0.5177(5) 0.5348(4) 0.153(4) Uani 1 1 d . . .
H14A H 0.8213 0.5196 0.4883 0.184 Uiso 1 1 calc R . .
H14B H 0.7780 0.5737 0.5479 0.184 Uiso 1 1 calc R . .
C15 C 0.9147(8) 0.4913(6) 0.5752(3) 0.138(3) Uani 1 1 d . . .
H15A H 0.9846 0.5320 0.5720 0.166 Uiso 1 1 calc R . .
H15B H 0.9454 0.4389 0.5580 0.166 Uiso 1 1 calc R . .
C16 C 0.8881(6) 0.4805(5) 0.6480(2) 0.106(2) Uani 1 1 d . . .
H16A H 0.9649 0.4557 0.6723 0.127 Uiso 1 1 calc R . .
H16B H 0.8730 0.5344 0.6676 0.127 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'
Ag Ag -0.8971 1.1015 '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'
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 Cl 169.00(11) . . ?
C1 Ag Ag 101.44(11) . 2_756 ?
Cl Ag Ag 82.74(4) . 2_756 ?
C1 N1 C3 110.3(4) . . ?
C1 N1 C4 124.3(4) . . ?
C3 N1 C4 125.3(4) . . ?
C1 N2 C2 111.5(3) . . ?
C1 N2 C11 122.3(3) . . ?
C2 N2 C11 126.1(4) . . ?
N2 C1 N1 104.1(3) . . ?
N2 C1 Ag 123.4(3) . . ?
N1 C1 Ag 132.5(3) . . ?
C3 C2 N2 106.6(4) . . ?
C3 C2 H2 126.7 . . ?
N2 C2 H2 126.7 . . ?
C2 C3 N1 107.5(4) . . ?
C2 C3 H3 126.3 . . ?
N1 C3 H3 126.3 . . ?
N1 C4 C5 112.3(3) . . ?
N1 C4 H4A 109.1 . . ?
C5 C4 H4A 109.2 . . ?
N1 C4 H4B 109.1 . . ?
C5 C4 H4B 109.1 . . ?
H4A C4 H4B 107.9 . . ?
C10 C5 C6 117.8(5) . . ?
C10 C5 C4 121.9(4) . . ?
C6 C5 C4 120.2(4) . . ?
C7 C6 C5 121.1(5) . . ?
C7 C6 H6 119.4 . . ?
C5 C6 H6 119.4 . . ?
C6 C7 C8 119.4(5) . . ?
C6 C7 H7 120.3 . . ?
C8 C7 H7 120.3 . . ?
C9 C8 C7 120.5(5) . . ?
C9 C8 H8 119.7 . . ?
C7 C8 H8 119.7 . . ?
C8 C9 C10 119.7(5) . . ?
C8 C9 H9 120.1 . . ?
C10 C9 H9 120.1 . . ?
C9 C10 C5 121.4(5) . . ?
C9 C10 H10 119.3 . . ?
C5 C10 H10 119.3 . . ?
C12 C11 C16 115.9(5) . . ?
C12 C11 N2 112.5(4) . . ?
C16 C11 N2 110.7(4) . . ?
C12 C11 H11 105.6 . . ?
C16 C11 H11 105.6 . . ?
N2 C11 H11 105.6 . . ?
C11 C12 C13 110.7(4) . . ?
C11 C12 H12A 109.5 . . ?
C13 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C13 C12 H12B 109.5 . . ?
H12A C12 H12B 108.1 . . ?
C14 C13 C12 111.8(6) . . ?
C14 C13 H13A 109.3 . . ?
C12 C13 H13A 109.3 . . ?
C14 C13 H13B 109.3 . . ?
C12 C13 H13B 109.3 . . ?
H13A C13 H13B 107.9 . . ?
C15 C14 C13 114.1(6) . . ?
C15 C14 H14A 108.7 . . ?
C13 C14 H14A 108.7 . . ?
C15 C14 H14B 108.7 . . ?
C13 C14 H14B 108.7 . . ?
H14A C14 H14B 107.6 . . ?
C14 C15 C16 112.3(7) . . ?
C14 C15 H15A 109.1 . . ?
C16 C15 H15A 109.1 . . ?
C14 C15 H15B 109.1 . . ?
C16 C15 H15B 109.1 . . ?
H15A C15 H15B 107.9 . . ?
C11 C16 C15 110.9(5) . . ?
C11 C16 H16A 109.5 . . ?
C15 C16 H16A 109.5 . . ?
C11 C16 H16B 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 108.0 . . ?
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 2.079(4) . ?
Ag Cl 2.3296(11) . ?
Ag Ag 2.8886(7) 2_756 ?
N1 C1 1.362(5) . ?
N1 C3 1.370(6) . ?
N1 C4 1.456(5) . ?
N2 C1 1.342(5) . ?
N2 C2 1.368(5) . ?
N2 C11 1.476(5) . ?
C2 C3 1.331(6) . ?
C2 H2 0.9300 . ?
C3 H3 0.9300 . ?
C4 C5 1.489(6) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C10 1.380(6) . ?
C5 C6 1.396(7) . ?
C6 C7 1.365(7) . ?
C6 H6 0.9300 . ?
C7 C8 1.390(7) . ?
C7 H7 0.9300 . ?
C8 C9 1.359(9) . ?
C8 H8 0.9300 . ?
C9 C10 1.376(8) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C11 C12 1.454(6) . ?
C11 C16 1.464(6) . ?
C11 H11 0.9800 . ?
C12 C13 1.540(8) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.471(12) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C15 1.423(12) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C16 1.511(7) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
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
C4 H4B Cl 0.97 2.88 3.827(5) 165.4 2_756
C12 H12A Cl 0.97 2.84 3.785(7) 163.9 3_455
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 N2 C1 N1 0.8(5) . . . . ?
C11 N2 C1 N1 176.9(3) . . . . ?
C2 N2 C1 Ag -179.7(3) . . . . ?
C11 N2 C1 Ag -3.6(6) . . . . ?
C3 N1 C1 N2 -0.4(5) . . . . ?
C4 N1 C1 N2 176.0(4) . . . . ?
C3 N1 C1 Ag -179.9(3) . . . . ?
C4 N1 C1 Ag -3.5(6) . . . . ?
Cl Ag C1 N2 2.5(9) . . . . ?
Ag Ag C1 N2 114.0(3) 2_756 . . . ?
Cl Ag C1 N1 -178.1(4) . . . . ?
Ag Ag C1 N1 -66.6(4) 2_756 . . . ?
C1 N2 C2 C3 -0.9(5) . . . . ?
C11 N2 C2 C3 -176.8(4) . . . . ?
N2 C2 C3 N1 0.6(5) . . . . ?
C1 N1 C3 C2 -0.1(5) . . . . ?
C4 N1 C3 C2 -176.5(4) . . . . ?
C1 N1 C4 C5 -105.6(5) . . . . ?
C3 N1 C4 C5 70.3(6) . . . . ?
N1 C4 C5 C10 -118.0(5) . . . . ?
N1 C4 C5 C6 62.6(6) . . . . ?
C10 C5 C6 C7 0.2(8) . . . . ?
C4 C5 C6 C7 179.7(5) . . . . ?
C5 C6 C7 C8 0.4(8) . . . . ?
C6 C7 C8 C9 -1.8(9) . . . . ?
C7 C8 C9 C10 2.5(9) . . . . ?
C8 C9 C10 C5 -1.9(8) . . . . ?
C6 C5 C10 C9 0.5(8) . . . . ?
C4 C5 C10 C9 -178.9(5) . . . . ?
C1 N2 C11 C12 127.5(5) . . . . ?
C2 N2 C11 C12 -57.1(7) . . . . ?
C1 N2 C11 C16 -101.1(6) . . . . ?
C2 N2 C11 C16 74.4(6) . . . . ?
C16 C11 C12 C13 49.7(8) . . . . ?
N2 C11 C12 C13 178.5(6) . . . . ?
C11 C12 C13 C14 -48.2(10) . . . . ?
C12 C13 C14 C15 52.4(11) . . . . ?
C13 C14 C15 C16 -54.3(11) . . . . ?
C12 C11 C16 C15 -51.2(8) . . . . ?
N2 C11 C16 C15 179.1(6) . . . . ?
C14 C15 C16 C11 51.8(10) . . . . ?
