#------------------------------------------------------------------------------
#$Date: 2019-11-26 04:08:01 +0200 (Tue, 26 Nov 2019) $
#$Revision: 242573 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/13/26/4132626.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_4132626
loop_
_publ_author_name
'Doud, Evan A.'
'Inkpen, Michael S.'
'Lovat, Giacomo'
'Montes, Enrique'
'Paley, Daniel W.'
'Steigerwald, Michael L.'
'Vázquez, Héctor'
'Venkataraman, Latha'
'Roy, Xavier'
_publ_section_title
;
 In Situ Formation of N-Heterocyclic Carbene-Bound Single-Molecule
 Junctions.
;
_journal_issue                   28
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              8944
_journal_page_last               8949
_journal_paper_doi               10.1021/jacs.8b05184
_journal_volume                  140
_journal_year                    2018
_chemical_formula_moiety         'C40 H48 Ag2 Cl2 N4 S2, 2(C H2 Cl2)'
_chemical_formula_sum            'C42 H52 Ag2 Cl6 N4 S2'
_chemical_formula_weight         1105.43
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-03-14
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_cell_angle_alpha                90
_cell_angle_beta                 106.365(5)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   14.2598(6)
_cell_length_b                   11.7679(5)
_cell_length_c                   15.0014(7)
_cell_measurement_reflns_used    3301
_cell_measurement_temperature    293.94(19)
_cell_measurement_theta_max      24.9530
_cell_measurement_theta_min      4.0790
_cell_volume                     2415.37(19)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      293.94(19)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0549
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.823
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
--------------------------------------------------------------------------
  1  ω    -12.00  45.00   1.00   10.00    --   17.19  19.00  90.00   57
  2  ω    -42.00  -9.00   1.00   10.00    --   17.19 -77.00  90.00   33
  3  ω    -50.00  31.00   1.00   10.00    --   17.19 -37.00 -90.00   81
  4  ω     39.00  81.00   1.00   10.00    --   17.19 178.00-150.00   42
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0189058000
_diffrn_orient_matrix_UB_12      0.0021974000
_diffrn_orient_matrix_UB_13      0.0389220000
_diffrn_orient_matrix_UB_21      0.0399554000
_diffrn_orient_matrix_UB_22      -0.0330426000
_diffrn_orient_matrix_UB_23      0.0260523000
_diffrn_orient_matrix_UB_31      0.0270668000
_diffrn_orient_matrix_UB_32      0.0503645000
_diffrn_orient_matrix_UB_33      0.0153719000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0283
_diffrn_reflns_av_unetI/netI     0.0468
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.823
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            11063
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.823
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.602
_diffrn_reflns_theta_min         3.318
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    1.262
_exptl_absorpt_correction_T_max  0.979
_exptl_absorpt_correction_T_min  0.954
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.520
_exptl_crystal_description       prism
_exptl_crystal_F_000             1120
_exptl_crystal_size_max          0.384
_exptl_crystal_size_mid          0.175
_exptl_crystal_size_min          0.088
_refine_diff_density_max         0.813
_refine_diff_density_min         -0.635
_refine_diff_density_rms         0.078
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     258
_refine_ls_number_reflns         5599
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0809
_refine_ls_R_factor_gt           0.0530
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0600P)²+2.0920P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1249
_refine_ls_wR_factor_ref         0.1433
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3954
_reflns_number_total             5599
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ja8b05184_si_005.cif
_cod_data_source_block           ed04199_2_corr
_cod_database_code               4132626
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'H C N S Cl Ag'
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_reflns_odcompleteness_completeness 98.75
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C11(H11), C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C21(H21A,H21B)
2.c Aromatic/amide H refined with riding coordinates:
 C19(H19), C4(H4), C6(H6), C3(H3), C18(H18), C15(H15), C16(H16)
2.d Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C10(H10A,H10B,H10C), C9(H9A,H9B,H9C), C12(H12A,H12B,
 H12C), C13(H13A,H13B,H13C)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.230
_oxdiff_exptl_absorpt_empirical_full_min 0.833
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
Ag1 Ag 0.46857(3) 0.85435(3) 0.53299(3) 0.06311(16) Uani 1 1 d .
Cl1 Cl 0.41998(8) 0.94722(10) 0.38562(7) 0.0570(3) Uani 1 1 d .
S1 S 0.83173(11) 0.14126(13) 1.14586(12) 0.0868(5) Uani 1 1 d .
N1 N 0.5704(2) 0.6876(3) 0.6893(2) 0.0513(8) Uani 1 1 d .
N2 N 0.4168(2) 0.6963(3) 0.6793(2) 0.0482(8) Uani 1 1 d .
C7 C 0.5568(3) 0.6171(3) 0.7590(3) 0.0428(8) Uani 1 1 d .
C5 C 0.5803(3) 0.4831(3) 0.8824(2) 0.0403(8) Uani 1 1 d .
C14 C 0.6428(3) 0.4023(3) 0.9501(2) 0.0415(8) Uani 1 1 d .
C2 C 0.4575(3) 0.6233(3) 0.7526(3) 0.0421(8) Uani 1 1 d .
C1 C 0.4849(3) 0.7352(4) 0.6407(3) 0.0510(10) Uani 1 1 d .
C19 C 0.7416(3) 0.4215(3) 0.9885(3) 0.0468(9) Uani 1 1 d .
H19 H 0.7687 0.4881 0.9733 0.056 Uiso 1 1 calc R
C4 C 0.4797(3) 0.4930(3) 0.8757(3) 0.0444(9) Uani 1 1 d .
H4 H 0.4544 0.4507 0.9160 0.053 Uiso 1 1 calc R
C6 C 0.6191(3) 0.5475(3) 0.8237(3) 0.0444(9) Uani 1 1 d .
H6 H 0.6853 0.5440 0.8278 0.053 Uiso 1 1 calc R
C3 C 0.4180(3) 0.5626(3) 0.8119(3) 0.0456(9) Uani 1 1 d .
H3 H 0.3521 0.5686 0.8088 0.055 Uiso 1 1 calc R
C18 C 0.8013(3) 0.3461(3) 1.0483(3) 0.0511(10) Uani 1 1 d .
H18 H 0.8674 0.3623 1.0733 0.061 Uiso 1 1 calc R
C15 C 0.6054(3) 0.3018(4) 0.9756(3) 0.0531(10) Uani 1 1 d .
H15 H 0.5390 0.2861 0.9522 0.064 Uiso 1 1 calc R
C17 C 0.7628(3) 0.2458(4) 1.0713(3) 0.0527(10) Uani 1 1 d .
C16 C 0.6646(3) 0.2257(4) 1.0346(3) 0.0586(11) Uani 1 1 d .
H16 H 0.6377 0.1591 1.0501 0.070 Uiso 1 1 calc R
C11 C 0.3113(3) 0.7246(4) 0.6474(3) 0.0647(13) Uani 1 1 d .
H11 H 0.2787 0.6788 0.6844 0.078 Uiso 1 1 calc R
C8 C 0.6642(3) 0.7099(5) 0.6685(4) 0.0733(15) Uani 1 1 d .
H8 H 0.6492 0.7605 0.6144 0.088 Uiso 1 1 calc R
C20 C 0.9543(4) 0.1725(6) 1.1520(5) 0.104(2) Uani 1 1 d .
H20A H 0.9613 0.1771 1.0903 0.156 Uiso 1 1 calc GR
H20B H 0.9959 0.1135 1.1858 0.156 Uiso 1 1 calc GR
H20C H 0.9723 0.2438 1.1832 0.156 Uiso 1 1 calc GR
C10 C 0.7043(5) 0.6015(6) 0.6390(5) 0.102(2) Uani 1 1 d .
H10A H 0.7308 0.5545 0.6925 0.153 Uiso 1 1 calc GR
H10B H 0.7550 0.6199 0.6107 0.153 Uiso 1 1 calc GR
H10C H 0.6528 0.5615 0.5953 0.153 Uiso 1 1 calc GR
C9 C 0.7339(4) 0.7727(6) 0.7453(5) 0.103(2) Uani 1 1 d .
H9A H 0.7044 0.8424 0.7569 0.154 Uiso 1 1 calc GR
H9B H 0.7924 0.7893 0.7280 0.154 Uiso 1 1 calc GR
H9C H 0.7499 0.7269 0.8005 0.154 Uiso 1 1 calc GR
C12 C 0.2950(5) 0.8467(6) 0.6667(5) 0.104(2) Uani 1 1 d .
H12A H 0.3224 0.8618 0.7318 0.155 Uiso 1 1 calc GR
H12B H 0.2261 0.8622 0.6494 0.155 Uiso 1 1 calc GR
H12C H 0.3259 0.8944 0.6314 0.155 Uiso 1 1 calc GR
C13 C 0.2682(4) 0.6910(7) 0.5475(5) 0.113(2) Uani 1 1 d .
H13A H 0.3007 0.7316 0.5093 0.169 Uiso 1 1 calc GR
H13B H 0.1998 0.7092 0.5285 0.169 Uiso 1 1 calc GR
H13C H 0.2765 0.6108 0.5409 0.169 Uiso 1 1 calc GR
Cl3 Cl 0.41295(17) 1.0833(2) 0.8367(2) 0.1644(11) Uani 1 1 d .
Cl2 Cl 0.5441(2) 0.8960(3) 0.8730(2) 0.1724(11) Uani 1 1 d .
C21 C 0.5159(6) 1.0239(8) 0.8228(6) 0.135(3) Uani 1 1 d .
H21A H 0.5087 1.0163 0.7568 0.162 Uiso 1 1 calc R
H21B H 0.5701 1.0752 0.8481 0.162 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'
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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -4 -5 0.1360
-5 -5 2 0.2021
2 -1 -5 0.1340
-2 4 -2 0.0010
2 -4 2 0.0873
5 2 -4 0.0775
-2 1 5 0.0410
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_3
Cl1 Ag1 Cl1 90.17(4) 3_676
C1 Ag1 Cl1 163.24(13) .
C1 Ag1 Cl1 106.58(13) 3_676
Ag1 Cl1 Ag1 89.83(4) 3_676
C20 S1 C17 104.7(2) .
C7 N1 C8 126.1(3) .
C1 N1 C7 110.9(3) .
C1 N1 C8 123.0(3) .
C2 N2 C11 123.7(3) .
C1 N2 C2 111.2(3) .
C1 N2 C11 125.1(3) .
N1 C7 C2 105.7(3) .
C6 C7 N1 133.1(3) .
C6 C7 C2 121.2(3) .
C4 C5 C14 120.1(3) .
C6 C5 C14 120.8(3) .
C6 C5 C4 119.2(3) .
C19 C14 C5 121.6(3) .
C19 C14 C15 116.6(4) .
C15 C14 C5 121.8(3) .
N2 C2 C7 106.0(3) .
C3 C2 N2 132.6(3) .
C3 C2 C7 121.4(4) .
N1 C1 Ag1 125.3(3) .
N2 C1 Ag1 128.5(3) .
N2 C1 N1 106.1(3) .
C14 C19 H19 118.7 .
C18 C19 C14 122.5(4) .
C18 C19 H19 118.7 .
C5 C4 H4 118.8 .
C3 C4 C5 122.4(3) .
C3 C4 H4 118.8 .
C7 C6 C5 118.4(3) .
C7 C6 H6 120.8 .
C5 C6 H6 120.8 .
C2 C3 H3 121.3 .
C4 C3 C2 117.4(3) .
C4 C3 H3 121.3 .
C19 C18 H18 120.1 .
C19 C18 C17 119.8(4) .
C17 C18 H18 120.1 .
C14 C15 H15 119.4 .
C16 C15 C14 121.2(4) .
C16 C15 H15 119.4 .
C18 C17 S1 124.3(3) .
C16 C17 S1 117.2(3) .
C16 C17 C18 118.5(4) .
C15 C16 C17 121.4(4) .
C15 C16 H16 119.3 .
C17 C16 H16 119.3 .
N2 C11 H11 107.1 .
N2 C11 C12 110.6(4) .
N2 C11 C13 110.9(4) .
C12 C11 H11 107.1 .
C12 C11 C13 113.8(5) .
C13 C11 H11 107.1 .
N1 C8 H8 106.4 .
N1 C8 C10 110.5(4) .
N1 C8 C9 111.8(5) .
C10 C8 H8 106.4 .
C9 C8 H8 106.4 .
C9 C8 C10 114.8(5) .
S1 C20 H20A 109.5 .
S1 C20 H20B 109.5 .
S1 C20 H20C 109.5 .
H20A C20 H20B 109.5 .
H20A C20 H20C 109.5 .
H20B C20 H20C 109.5 .
C8 C10 H10A 109.5 .
C8 C10 H10B 109.5 .
C8 C10 H10C 109.5 .
H10A C10 H10B 109.5 .
H10A C10 H10C 109.5 .
H10B C10 H10C 109.5 .
C8 C9 H9A 109.5 .
C8 C9 H9B 109.5 .
C8 C9 H9C 109.5 .
H9A C9 H9B 109.5 .
H9A C9 H9C 109.5 .
H9B C9 H9C 109.5 .
C11 C12 H12A 109.5 .
C11 C12 H12B 109.5 .
C11 C12 H12C 109.5 .
H12A C12 H12B 109.5 .
H12A C12 H12C 109.5 .
H12B C12 H12C 109.5 .
C11 C13 H13A 109.5 .
C11 C13 H13B 109.5 .
C11 C13 H13C 109.5 .
H13A C13 H13B 109.5 .
H13A C13 H13C 109.5 .
H13B C13 H13C 109.5 .
Cl3 C21 H21A 108.5 .
Cl3 C21 H21B 108.5 .
Cl2 C21 Cl3 114.9(4) .
Cl2 C21 H21A 108.5 .
Cl2 C21 H21B 108.5 .
H21A C21 H21B 107.5 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Ag1 Cl1 2.3871(11) .
Ag1 Cl1 2.8941(12) 3_676
Ag1 C1 2.102(4) .
Cl1 Ag1 2.8941(12) 3_676
S1 C17 1.764(4) .
S1 C20 1.762(6) .
N1 C7 1.390(5) .
N1 C1 1.353(5) .
N1 C8 1.480(5) .
N2 C2 1.387(5) .
N2 C1 1.343(5) .
N2 C11 1.482(5) .
C7 C2 1.395(5) .
C7 C6 1.384(5) .
C5 C14 1.489(5) .
C5 C4 1.413(5) .
C5 C6 1.390(5) .
C14 C19 1.383(5) .
C14 C15 1.395(6) .
C2 C3 1.378(5) .
C19 H19 0.9300 .
C19 C18 1.374(5) .
C4 H4 0.9300 .
C4 C3 1.374(5) .
C6 H6 0.9300 .
C3 H3 0.9300 .
C18 H18 0.9300 .
C18 C17 1.385(6) .
C15 H15 0.9300 .
C15 C16 1.369(6) .
C17 C16 1.374(6) .
C16 H16 0.9300 .
C11 H11 0.9800 .
C11 C12 1.497(8) .
C11 C13 1.504(8) .
C8 H8 0.9800 .
C8 C10 1.514(8) .
C8 C9 1.489(9) .
C20 H20A 0.9600 .
C20 H20B 0.9600 .
C20 H20C 0.9600 .
C10 H10A 0.9600 .
C10 H10B 0.9600 .
C10 H10C 0.9600 .
C9 H9A 0.9600 .
C9 H9B 0.9600 .
C9 H9C 0.9600 .
C12 H12A 0.9600 .
C12 H12B 0.9600 .
C12 H12C 0.9600 .
C13 H13A 0.9600 .
C13 H13B 0.9600 .
C13 H13C 0.9600 .
Cl3 C21 1.692(8) .
Cl2 C21 1.680(9) .
C21 H21A 0.9700 .
C21 H21B 0.9700 .
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0.0000 -4.0001 -4.9999 -0.2034 0.0019 -0.2783
-5.0000 -5.0000 2.0000 0.1614 0.0175 -0.3564
2.0000 -1.0000 -4.9999 -0.2346 -0.0173 -0.0731
-2.0000 4.0000 -1.9999 -0.0312 -0.2642 0.1166
2.0000 -4.0000 1.9999 0.0312 0.2642 -0.1166
5.0000 2.0000 -4.0000 -0.2458 0.0295 0.1746
-2.0000 1.0000 4.9999 0.2346 0.0173 0.0731
