#------------------------------------------------------------------------------
#$Date: 2016-03-21 07:34:13 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178571 $
#$URL: svn://www.crystallography.net/cod/cif/4/06/81/4068122.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_4068122
loop_
_publ_author_name
'Keske, Eric C.'
'Zenkina, Olena V.'
'Wang, Ruiyao'
'Crudden, Cathleen M.'
_publ_section_title
;
 Synthesis and Structure of Silver and Rhodium 1,2,3-Triazol-5-ylidene
 Mesoionic Carbene Complexes
;
_journal_issue                   1
_journal_name_full               Organometallics
_journal_page_first              456
_journal_paper_doi               10.1021/om201104f
_journal_volume                  31
_journal_year                    2012
_chemical_formula_sum            'C74 H94 Ag4 Br4 Cl6 N12'
_chemical_formula_weight         2115.43
_space_group_IT_number           12
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2y'
_symmetry_space_group_name_H-M   'C 1 2/m 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                 117.3400(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   17.0605(2)
_cell_length_b                   23.2997(3)
_cell_length_c                   11.8865(3)
_cell_measurement_reflns_used    8546
_cell_measurement_temperature    180(2)
_cell_measurement_theta_max      26.29
_cell_measurement_theta_min      2.49
_cell_volume                     4197.15(13)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      180(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω 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  0.0271
_diffrn_reflns_av_sigmaI/netI    0.0190
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            24206
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         1.75
_exptl_absorpt_coefficient_mu    3.062
_exptl_absorpt_correction_T_max  0.6566
_exptl_absorpt_correction_T_min  0.5149
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.674
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             2104
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         2.755
_refine_diff_density_min         -2.539
_refine_diff_density_rms         0.216
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.108
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     240
_refine_ls_number_reflns         4240
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.109
_refine_ls_R_factor_all          0.0863
_refine_ls_R_factor_gt           0.0752
_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)+(0.1473P)²+41.4858P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2311
_refine_ls_wR_factor_ref         0.2446
_reflns_number_gt                3599
_reflns_number_total             4240
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om201104f_si_002.cif
_cod_data_source_block           cc104
_cod_original_cell_volume        4197.14(13)
_cod_original_sg_symbol_H-M      C2/m
_cod_database_code               4068122
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x, -y, z'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, 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
Ag1 Ag 1.0000 0.65509(3) 0.5000 0.0315(3) Uani 1 2 d S
Ag2 Ag 0.52839(11) 0.5000 0.64985(15) 0.0870(5) Uani 1 2 d S
N1 N 0.7273(4) 0.6235(3) 0.2637(6) 0.0398(13) Uani 1 1 d .
N2 N 0.7315(4) 0.6742(3) 0.2168(6) 0.0403(13) Uani 1 1 d .
N3 N 0.8162(3) 0.6890(2) 0.2871(5) 0.0321(11) Uani 1 1 d .
Br1 Br 0.55546(13) 0.5000 0.8771(2) 0.0863(5) Uani 1 2 d S
Br2 Br 0.63524(12) 0.5000 0.5449(2) 0.0860(5) Uani 1 2 d S
C1 C 0.9030(7) 0.5000 0.6218(10) 0.044(2) Uani 1 2 d S
H1A H 0.9391 0.5000 0.7109 0.053 Uiso 1 2 calc SR
C2 C 0.8768(5) 0.5514(3) 0.5574(7) 0.0398(15) Uani 1 1 d .
H2A H 0.8951 0.5866 0.6023 0.048 Uiso 1 1 calc R
C3 C 0.8239(4) 0.5518(3) 0.4266(7) 0.0355(14) Uani 1 1 d .
C4 C 0.7968(6) 0.5000 0.3613(9) 0.0349(19) Uani 1 2 d S
H4A H 0.7599 0.5000 0.2723 0.042 Uiso 1 2 calc SR
C5 C 0.8063(4) 0.6068(3) 0.3594(6) 0.0330(13) Uani 1 1 d .
C6 C 0.8662(4) 0.6503(3) 0.3756(7) 0.0339(13) Uani 1 1 d .
C7 C 0.6414(5) 0.5937(4) 0.2102(10) 0.057(2) Uani 1 1 d .
H7A H 0.5945 0.6214 0.1953 0.085 Uiso 1 1 calc R
H7B H 0.6424 0.5643 0.2700 0.085 Uiso 1 1 calc R
H7C H 0.6302 0.5754 0.1300 0.085 Uiso 1 1 calc R
C8 C 0.8468(4) 0.7427(3) 0.2574(7) 0.0376(14) Uani 1 1 d .
C9 C 0.8433(5) 0.7920(3) 0.3197(7) 0.0398(15) Uani 1 1 d .
C10 C 0.8716(6) 0.8430(3) 0.2881(9) 0.053(2) Uani 1 1 d .
H10A H 0.8697 0.8779 0.3282 0.063 Uiso 1 1 calc R
C11 C 0.9024(7) 0.8429(4) 0.1987(11) 0.064(3) Uani 1 1 d .
H11A H 0.9205 0.8779 0.1768 0.077 Uiso 1 1 calc R
C12 C 0.9071(6) 0.7928(4) 0.1415(10) 0.062(2) Uani 1 1 d .
H12A H 0.9288 0.7936 0.0809 0.074 Uiso 1 1 calc R
C13 C 0.8802(5) 0.7404(4) 0.1710(8) 0.0471(17) Uani 1 1 d .
C14 C 0.8108(5) 0.7920(3) 0.4206(8) 0.0459(17) Uani 1 1 d .
H14A H 0.7866 0.7530 0.4218 0.055 Uiso 1 1 calc R
C15 C 0.7372(7) 0.8355(5) 0.3882(11) 0.068(3) Uani 1 1 d .
H15A H 0.7090 0.8293 0.4428 0.101 Uiso 1 1 calc R
H15B H 0.6933 0.8309 0.2993 0.101 Uiso 1 1 calc R
H15C H 0.7617 0.8744 0.4014 0.101 Uiso 1 1 calc R
C16 C 0.8869(7) 0.8035(6) 0.5512(10) 0.072(3) Uani 1 1 d .
H16A H 0.8654 0.8020 0.6147 0.109 Uiso 1 1 calc R
H16B H 0.9116 0.8416 0.5522 0.109 Uiso 1 1 calc R
H16C H 0.9328 0.7743 0.5707 0.109 Uiso 1 1 calc R
C17 C 0.8915(6) 0.6843(4) 0.1150(9) 0.058(2) Uani 1 1 d .
H17A H 0.8632 0.6530 0.1411 0.069 Uiso 1 1 calc R
C18 C 0.8491(8) 0.6858(6) -0.0266(10) 0.084(3) Uani 1 1 d .
H18A H 0.7850 0.6820 -0.0605 0.126 Uiso 1 1 calc R
H18B H 0.8717 0.6541 -0.0575 0.126 Uiso 1 1 calc R
H18C H 0.8627 0.7224 -0.0544 0.126 Uiso 1 1 calc R
C19 C 0.9909(8) 0.6717(7) 0.1729(12) 0.099(5) Uani 1 1 d .
H19A H 1.0000 0.6333 0.1473 0.149 Uiso 1 1 calc R
H19B H 1.0170 0.6735 0.2655 0.149 Uiso 1 1 calc R
H19C H 1.0192 0.7003 0.1430 0.149 Uiso 1 1 calc R
Cl2 Cl 0.8224(9) 0.5298(7) 0.0792(11) 0.340(9) Uani 1 1 d D
Cl1 Cl 0.8678(14) 0.5000 -0.0994(17) 0.340(9) Uani 1 2 d SD
C21 C 0.798(2) 0.5000 -0.051(3) 0.146(17) Uani 0.60 2 d SPD
C20 C 0.884(3) 0.5000 0.038(3) 0.146(17) Uani 0.40 2 d SPD
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'
Br Br -0.2901 2.4595 '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
C6 Ag1 C6 173.9(3) . 2_756
Br1 Ag2 Br2 132.80(9) . .
Br1 Ag2 Br2 121.96(8) . 5_666
Br2 Ag2 Br2 105.23(7) . 5_666
Br1 Ag2 Ag2 173.92(10) . 5_666
Br2 Ag2 Ag2 53.27(6) . 5_666
Br2 Ag2 Ag2 51.96(6) 5_666 5_666
N2 N1 C5 112.5(5) . .
N2 N1 C7 118.4(6) . .
C5 N1 C7 129.1(6) . .
N1 N2 N3 102.7(5) . .
N2 N3 C6 115.3(5) . .
N2 N3 C8 118.2(5) . .
C6 N3 C8 126.4(5) . .
Ag2 Br2 Ag2 74.77(7) . 5_666
C2 C1 C2 120.3(9) 6_565 .
C2 C1 H1A 119.8 6_565 .
C2 C1 H1A 119.8 . .
C1 C2 C3 120.3(7) . .
C1 C2 H2A 119.9 . .
C3 C2 H2A 119.9 . .
C2 C3 C4 119.6(6) . .
C2 C3 C5 118.7(6) . .
C4 C3 C5 121.4(6) . .
C3 C4 C3 119.9(9) . 6_565
C3 C4 H4A 120.0 . .
C3 C4 H4A 120.0 6_565 .
N1 C5 C6 106.8(6) . .
N1 C5 C3 125.6(6) . .
C6 C5 C3 127.5(6) . .
N3 C6 C5 102.6(6) . .
N3 C6 Ag1 127.9(5) . .
C5 C6 Ag1 129.5(5) . .
N1 C7 H7A 109.5 . .
N1 C7 H7B 109.5 . .
H7A C7 H7B 109.5 . .
N1 C7 H7C 109.5 . .
H7A C7 H7C 109.5 . .
H7B C7 H7C 109.5 . .
C9 C8 C13 124.2(7) . .
C9 C8 N3 118.3(6) . .
C13 C8 N3 117.5(6) . .
C8 C9 C10 117.2(7) . .
C8 C9 C14 122.6(6) . .
C10 C9 C14 120.2(7) . .
C11 C10 C9 120.3(8) . .
C11 C10 H10A 119.8 . .
C9 C10 H10A 119.8 . .
C12 C11 C10 120.7(8) . .
C12 C11 H11A 119.7 . .
C10 C11 H11A 119.7 . .
C11 C12 C13 121.1(8) . .
C11 C12 H12A 119.4 . .
C13 C12 H12A 119.4 . .
C8 C13 C12 116.4(8) . .
C8 C13 C17 122.4(7) . .
C12 C13 C17 121.2(8) . .
C15 C14 C16 111.1(8) . .
C15 C14 C9 110.8(7) . .
C16 C14 C9 110.6(7) . .
C15 C14 H14A 108.1 . .
C16 C14 H14A 108.1 . .
C9 C14 H14A 108.1 . .
C14 C15 H15A 109.5 . .
C14 C15 H15B 109.5 . .
H15A C15 H15B 109.5 . .
C14 C15 H15C 109.5 . .
H15A C15 H15C 109.5 . .
H15B C15 H15C 109.5 . .
C14 C16 H16A 109.5 . .
C14 C16 H16B 109.5 . .
H16A C16 H16B 109.5 . .
C14 C16 H16C 109.5 . .
H16A C16 H16C 109.5 . .
H16B C16 H16C 109.5 . .
C18 C17 C13 112.3(8) . .
C18 C17 C19 111.9(9) . .
C13 C17 C19 107.7(9) . .
C18 C17 H17A 108.3 . .
C13 C17 H17A 108.3 . .
C19 C17 H17A 108.3 . .
C17 C18 H18A 109.5 . .
C17 C18 H18B 109.5 . .
H18A C18 H18B 109.5 . .
C17 C18 H18C 109.5 . .
H18A C18 H18C 109.5 . .
H18B C18 H18C 109.5 . .
C17 C19 H19A 109.5 . .
C17 C19 H19B 109.5 . .
H19A C19 H19B 109.5 . .
C17 C19 H19C 109.5 . .
H19A C19 H19C 109.5 . .
H19B C19 H19C 109.5 . .
Cl2 Cl2 C20 62.9(8) 6_565 .
Cl2 Cl2 C21 63.7(8) 6_565 .
C20 Cl2 C21 52(3) . .
C20 Cl1 C21 53(3) . .
C20 C21 Cl1 62.8(14) . .
C20 C21 Cl2 62.3(14) . .
Cl1 C21 Cl2 118(2) . .
C20 C21 Cl2 62.3(14) . 6_565
Cl1 C21 Cl2 118(2) . 6_565
Cl2 C21 Cl2 52.6(15) . 6_565
C21 C20 Cl1 64.6(16) . .
C21 C20 Cl2 65.5(16) . 6_565
Cl1 C20 Cl2 122(3) . 6_565
C21 C20 Cl2 65.5(16) . .
Cl1 C20 Cl2 122(3) . .
Cl2 C20 Cl2 54.3(16) 6_565 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Ag1 C6 2.075(7) .
Ag1 C6 2.075(7) 2_756
Ag2 Br1 2.523(3) .
Ag2 Br2 2.640(2) .
Ag2 Br2 2.686(3) 5_666
Ag2 Ag2 3.234(3) 5_666
N1 N2 1.321(9) .
N1 C5 1.362(9) .
N1 C7 1.477(9) .
N2 N3 1.340(8) .
N3 C6 1.350(8) .
N3 C8 1.459(8) .
Br2 Ag2 2.686(3) 5_666
C1 C2 1.381(9) 6_565
C1 C2 1.381(9) .
C1 H1A 0.9500 .
C2 C3 1.393(10) .
C2 H2A 0.9500 .
C3 C4 1.395(8) .
C3 C5 1.466(9) .
C4 C3 1.395(8) 6_565
C4 H4A 0.9500 .
C5 C6 1.389(9) .
C7 H7A 0.9800 .
C7 H7B 0.9800 .
C7 H7C 0.9800 .
C8 C9 1.383(10) .
C8 C13 1.386(11) .
C9 C10 1.398(10) .
C9 C14 1.535(11) .
C10 C11 1.385(14) .
C10 H10A 0.9500 .
C11 C12 1.372(15) .
C11 H11A 0.9500 .
C12 C13 1.404(12) .
C12 H12A 0.9500 .
C13 C17 1.519(12) .
C14 C15 1.520(12) .
C14 C16 1.522(13) .
C14 H14A 1.0000 .
C15 H15A 0.9800 .
C15 H15B 0.9800 .
C15 H15C 0.9800 .
C16 H16A 0.9800 .
C16 H16B 0.9800 .
C16 H16C 0.9800 .
C17 C18 1.496(13) .
C17 C19 1.537(14) .
C17 H17A 1.0000 .
C18 H18A 0.9800 .
C18 H18B 0.9800 .
C18 H18C 0.9800 .
C19 H19A 0.9800 .
C19 H19B 0.9800 .
C19 H19C 0.9800 .
Cl2 Cl2 1.39(3) 6_565
Cl2 C20 1.52(2) .
Cl2 C21 1.56(2) .
Cl1 C20 1.52(2) .
Cl1 C21 1.54(2) .
C21 C20 1.36(8) .
C21 Cl2 1.56(2) 6_565
C20 Cl2 1.52(2) 6_565
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
C5 N1 N2 N3 -0.3(8) . .
C7 N1 N2 N3 178.6(7) . .
N1 N2 N3 C6 0.4(8) . .
N1 N2 N3 C8 177.1(6) . .
Br1 Ag2 Br2 Ag2 180.0 . 5_666
Br2 Ag2 Br2 Ag2 0.0 5_666 5_666
C2 C1 C2 C3 0.0(16) 6_565 .
C1 C2 C3 C4 0.5(12) . .
C1 C2 C3 C5 -172.7(8) . .
C2 C3 C4 C3 -1.0(14) . 6_565
C5 C3 C4 C3 172.0(5) . 6_565
N2 N1 C5 C6 0.1(8) . .
C7 N1 C5 C6 -178.7(8) . .
N2 N1 C5 C3 -177.2(6) . .
C7 N1 C5 C3 4.0(12) . .
C2 C3 C5 N1 -139.3(7) . .
C4 C3 C5 N1 47.6(11) . .
C2 C3 C5 C6 44.0(10) . .
C4 C3 C5 C6 -129.1(8) . .
N2 N3 C6 C5 -0.4(8) . .
C8 N3 C6 C5 -176.7(6) . .
N2 N3 C6 Ag1 178.1(5) . .
C8 N3 C6 Ag1 1.8(10) . .
N1 C5 C6 N3 0.2(7) . .
C3 C5 C6 N3 177.4(6) . .
N1 C5 C6 Ag1 -178.3(5) . .
C3 C5 C6 Ag1 -1.1(11) . .
C6 Ag1 C6 N3 -152.7(6) 2_756 .
C6 Ag1 C6 C5 25.4(6) 2_756 .
N2 N3 C8 C9 91.9(8) . .
C6 N3 C8 C9 -91.9(8) . .
N2 N3 C8 C13 -90.2(8) . .
C6 N3 C8 C13 86.0(9) . .
C13 C8 C9 C10 3.2(11) . .
N3 C8 C9 C10 -179.0(6) . .
C13 C8 C9 C14 -176.2(7) . .
N3 C8 C9 C14 1.5(10) . .
C8 C9 C10 C11 -0.6(12) . .
C14 C9 C10 C11 178.8(8) . .
C9 C10 C11 C12 -1.1(15) . .
C10 C11 C12 C13 0.5(15) . .
C9 C8 C13 C12 -3.8(11) . .
N3 C8 C13 C12 178.4(7) . .
C9 C8 C13 C17 173.5(7) . .
N3 C8 C13 C17 -4.3(11) . .
C11 C12 C13 C8 1.8(13) . .
C11 C12 C13 C17 -175.5(9) . .
C8 C9 C14 C15 -125.8(8) . .
C10 C9 C14 C15 54.7(10) . .
C8 C9 C14 C16 110.6(9) . .
C10 C9 C14 C16 -68.9(10) . .
C8 C13 C17 C18 127.7(9) . .
C12 C13 C17 C18 -55.1(12) . .
C8 C13 C17 C19 -108.7(10) . .
C12 C13 C17 C19 68.5(11) . .
C20 Cl1 C21 Cl2 30.1(13) . .
C20 Cl1 C21 Cl2 -30.1(13) . 6_565
Cl2 Cl2 C21 C20 -74.9(8) 6_565 .
Cl2 Cl2 C21 Cl1 -105.2(17) 6_565 .
C20 Cl2 C21 Cl1 -30.3(13) . .
C20 Cl2 C21 Cl2 74.9(8) . 6_565
Cl2 C21 C20 Cl1 -149.9(8) . .
Cl2 C21 C20 Cl1 149.9(8) 6_565 .
Cl1 C21 C20 Cl2 -149.9(8) . 6_565
Cl2 C21 C20 Cl2 60.1(15) . 6_565
Cl1 C21 C20 Cl2 149.9(8) . .
Cl2 C21 C20 Cl2 -60.1(15) 6_565 .
C21 Cl1 C20 Cl2 32.6(17) . 6_565
C21 Cl1 C20 Cl2 -32.6(17) . .
Cl2 Cl2 C20 C21 76.5(9) 6_565 .
Cl2 Cl2 C20 Cl1 109(2) 6_565 .
C21 Cl2 C20 Cl1 32.3(17) . .
C21 Cl2 C20 Cl2 -76.5(9) . 6_565
