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#$Date: 2023-04-20 14:53:48 +0300 (Thu, 20 Apr 2023) $
#$Revision: 282777 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/10/08/1100866.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_1100866
loop_
_publ_author_name
'de Frémont, Pierre'
'Scott, Natalie M.'
'Stevens, Edwin D.'
'Nolan, Steven P.'
_publ_section_title
;
 Synthesis and Structural Characterization of N -Heterocyclic
 Carbene Gold(I) Complexes
;
_journal_issue                   10
_journal_name_full               Organometallics
_journal_page_first              2411
_journal_page_last               2418
_journal_paper_doi               10.1021/om050111c
_journal_volume                  24
_journal_year                    2005
_chemical_formula_sum            'C11 H11 Au Cl N3'
_chemical_formula_weight         417.64
_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
_cell_angle_alpha                91.9290(10)
_cell_angle_beta                 91.3230(10)
_cell_angle_gamma                101.5470(10)
_cell_formula_units_Z            4
_cell_length_a                   7.3539(4)
_cell_length_b                   10.8603(5)
_cell_length_c                   14.5517(7)
_cell_measurement_reflns_used    17736
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      30.728
_cell_measurement_theta_min      2.329
_cell_volume                     1137.48(10)
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0420
_diffrn_reflns_av_sigmaI/netI    0.0368
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            10117
_diffrn_reflns_theta_full        22.50
_diffrn_reflns_theta_max         22.50
_diffrn_reflns_theta_min         2.33
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_exptl_absorpt_coefficient_mu    13.141
_exptl_absorpt_correction_T_max  1.000000
_exptl_absorpt_correction_T_min  0.384732
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    2.439
_exptl_crystal_density_meas      0
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.8
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.4
_refine_diff_density_max         1.036
_refine_diff_density_min         -1.294
_refine_diff_density_rms         0.147
_refine_ls_extinction_coef       0.0040(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     290
_refine_ls_number_reflns         2972
_refine_ls_number_restraints     278
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0218
_refine_ls_R_factor_gt           0.0214
_refine_ls_shift/su_max          0.186
_refine_ls_shift/su_mean         0.006
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0312P)²+3.4083P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0634
_refine_ls_wR_factor_ref         0.0637
_reflns_number_gt                2924
_reflns_number_total             2972
_reflns_threshold_expression     >2sigma(I)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               1100866
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
Au1 Au 0.20267(3) 0.036777(17) 0.074184(13) 0.01374(12) Uani 1 1 d U . .
Cl1 Cl 0.16155(19) 0.22419(12) 0.13824(9) 0.0202(3) Uani 1 1 d U . .
N1 N 0.2896(6) -0.1246(4) -0.0782(3) 0.0139(9) Uani 1 1 d U . .
C1 C 0.2484(7) -0.1179(5) 0.0111(4) 0.0137(10) Uani 1 1 d U . .
Au2 Au 0.26622(3) 0.521694(18) 0.548074(13) 0.01682(12) Uani 1 1 d U . .
Cl2 Cl 0.2656(2) 0.73160(12) 0.54384(9) 0.0253(3) Uani 1 1 d U . .
N2 N 0.2476(6) -0.2371(4) 0.0375(3) 0.0155(9) Uani 1 1 d U . .
C2 C 0.3043(7) -0.2426(5) -0.1039(4) 0.0160(11) Uani 1 1 d U . .
N3 N 0.2804(6) -0.3165(4) -0.0349(3) 0.0179(10) Uani 1 1 d U . .
C3 C 0.3406(8) -0.2527(5) -0.2043(4) 0.0213(12) Uani 1 1 d U . .
H3A H 0.2312 -0.3021 -0.2390 0.026 Uiso 1 1 calc R . .
H3B H 0.4495 -0.2914 -0.2153 0.026 Uiso 1 1 calc R . .
N4 N 0.2453(6) 0.2526(4) 0.4843(3) 0.0172(9) Uani 1 1 d U . .
C4 C 0.3792(9) -0.1125(5) -0.2307(4) 0.0246(13) Uani 1 1 d U . .
H4A H 0.5143 -0.0800 -0.2350 0.030 Uiso 1 1 calc R . .
H4B H 0.3184 -0.1034 -0.2908 0.030 Uiso 1 1 calc R . .
N5 N 0.2915(6) 0.2725(4) 0.6280(3) 0.0168(9) Uani 1 1 d U . .
C5 C 0.2997(8) -0.0403(5) -0.1547(4) 0.0182(12) Uani 1 1 d U . .
H5A H 0.3828 0.0417 -0.1391 0.022 Uiso 1 1 calc R . .
H5B H 0.1752 -0.0260 -0.1729 0.022 Uiso 1 1 calc R . .
N6 N 0.2848(7) 0.1454(4) 0.6068(3) 0.0202(10) Uani 1 1 d U . .
C6 C 0.2128(7) -0.2877(5) 0.1261(4) 0.0143(10) Uani 1 1 d U . .
C7 C 0.2692(7) -0.2136(5) 0.2051(4) 0.0170(11) Uani 1 1 d U . .
H7 H 0.3339 -0.1292 0.2006 0.020 Uiso 1 1 calc R . .
C8 C 0.2303(8) -0.2636(5) 0.2909(4) 0.0201(12) Uani 1 1 d U . .
H8 H 0.2670 -0.2131 0.3453 0.024 Uiso 1 1 calc R . .
C9 C 0.1376(8) -0.3878(5) 0.2968(4) 0.0216(12) Uani 1 1 d U . .
H9 H 0.1105 -0.4223 0.3552 0.026 Uiso 1 1 calc R . .
C10 C 0.0849(7) -0.4611(5) 0.2170(4) 0.0204(12) Uani 1 1 d U . .
H10 H 0.0223 -0.5461 0.2211 0.024 Uiso 1 1 calc R . .
C11 C 0.1227(7) -0.4118(5) 0.1316(4) 0.0168(11) Uani 1 1 d U . .
H11 H 0.0872 -0.4626 0.0772 0.020 Uiso 1 1 calc R . .
C12 C 0.2685(7) 0.3409(5) 0.5546(4) 0.0160(11) Uani 1 1 d U . .
C13 C 0.2589(8) 0.1389(5) 0.5181(4) 0.0200(11) Uani 1 1 d U . .
C14 C 0.2404(9) 0.0412(6) 0.4425(4) 0.0278(13) Uani 1 1 d U . .
H14A H 0.1595 -0.0386 0.4594 0.033 Uiso 1 1 calc R . .
H14B H 0.3628 0.0249 0.4247 0.033 Uiso 1 1 calc R . .
C15 C 0.1482(9) 0.1062(6) 0.3643(4) 0.0292(13) Uani 1 1 d U . .
H15A H 0.1885 0.0815 0.3032 0.035 Uiso 1 1 calc R . .
H15B H 0.0111 0.0825 0.3658 0.035 Uiso 1 1 calc R . .
C16 C 0.2141(9) 0.2477(6) 0.3842(4) 0.0247(13) Uani 1 1 d U . .
H16A H 0.3300 0.2809 0.3522 0.030 Uiso 1 1 calc R . .
H16B H 0.1178 0.2950 0.3663 0.030 Uiso 1 1 calc R . .
C17 C 0.3100(8) 0.3133(5) 0.7227(4) 0.0154(11) Uani 1 1 d U . .
C18 C 0.2116(8) 0.2357(5) 0.7862(4) 0.0179(12) Uani 1 1 d U . .
H18 H 0.1312 0.1593 0.7663 0.021 Uiso 1 1 calc R . .
C19 C 0.2314(8) 0.2704(5) 0.8789(4) 0.0201(12) Uani 1 1 d U . .
H19 H 0.1660 0.2174 0.9230 0.024 Uiso 1 1 calc R . .
C20 C 0.3476(8) 0.3835(5) 0.9073(4) 0.0217(12) Uani 1 1 d U . .
H20 H 0.3603 0.4081 0.9707 0.026 Uiso 1 1 calc R . .
C21 C 0.4446(8) 0.4601(5) 0.8433(4) 0.0218(12) Uani 1 1 d U . .
H21 H 0.5237 0.5371 0.8631 0.026 Uiso 1 1 calc R . .
C22 C 0.4274(7) 0.4257(5) 0.7512(4) 0.0161(11) Uani 1 1 d U . .
H22 H 0.4951 0.4781 0.7075 0.019 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'
Au Au -2.0133 8.8022 '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 Au1 Cl1 175.59(15) . . ?
C1 N1 C2 110.6(4) . . ?
C1 N1 C5 135.4(4) . . ?
C2 N1 C5 113.4(4) . . ?
N1 C1 N2 102.3(4) . . ?
N1 C1 Au1 123.4(4) . . ?
N2 C1 Au1 134.3(4) . . ?
C12 Au2 Cl2 178.74(16) . . ?
C1 N2 N3 112.7(4) . . ?
C1 N2 C6 128.4(4) . . ?
N3 N2 C6 118.8(4) . . ?
N3 C2 N1 111.3(5) . . ?
N3 C2 C3 137.6(5) . . ?
N1 C2 C3 111.2(4) . . ?
C2 N3 N2 103.0(4) . . ?
C2 C3 C4 101.9(4) . . ?
C13 N4 C12 109.5(5) . . ?
C13 N4 C16 113.0(5) . . ?
C12 N4 C16 137.5(5) . . ?
C5 C4 C3 106.6(5) . . ?
C12 N5 N6 114.3(4) . . ?
C12 N5 C17 127.8(4) . . ?
N6 N5 C17 117.8(4) . . ?
N1 C5 C4 102.5(4) . . ?
C13 N6 N5 102.4(4) . . ?
C11 C6 C7 120.7(5) . . ?
C11 C6 N2 118.9(5) . . ?
C7 C6 N2 120.4(5) . . ?
C6 C7 C8 119.7(5) . . ?
C9 C8 C7 119.8(5) . . ?
C8 C9 C10 119.8(5) . . ?
C11 C10 C9 120.7(5) . . ?
C10 C11 C6 119.4(5) . . ?
N5 C12 N4 102.0(4) . . ?
N5 C12 Au2 129.9(4) . . ?
N4 C12 Au2 128.1(4) . . ?
N6 C13 N4 111.8(5) . . ?
N6 C13 C14 137.4(5) . . ?
N4 C13 C14 110.8(5) . . ?
C13 C14 C15 100.7(5) . . ?
C16 C15 C14 105.3(5) . . ?
N4 C16 C15 101.4(4) . . ?
C18 C17 C22 120.7(5) . . ?
C18 C17 N5 118.2(5) . . ?
C22 C17 N5 121.1(5) . . ?
C17 C18 C19 119.6(5) . . ?
C20 C19 C18 119.7(5) . . ?
C21 C20 C19 120.2(5) . . ?
C22 C21 C20 120.5(5) . . ?
C21 C22 C17 119.4(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
Au1 C1 1.979(5) . ?
Au1 Cl1 2.2880(13) . ?
N1 C1 1.344(7) . ?
N1 C2 1.349(7) . ?
N1 C5 1.459(7) . ?
C1 N2 1.361(7) . ?
Au2 C12 1.972(5) . ?
Au2 Cl2 2.2835(13) . ?
N2 N3 1.395(6) . ?
N2 C6 1.426(7) . ?
C2 N3 1.299(7) . ?
C2 C3 1.496(8) . ?
C3 C4 1.555(8) . ?
N4 C13 1.365(7) . ?
N4 C12 1.363(7) . ?
N4 C16 1.467(7) . ?
C4 C5 1.527(8) . ?
N5 C12 1.347(7) . ?
N5 N6 1.395(6) . ?
N5 C17 1.429(7) . ?
N6 C13 1.298(7) . ?
C6 C11 1.384(8) . ?
C6 C7 1.387(8) . ?
C7 C8 1.392(8) . ?
C8 C9 1.390(8) . ?
C9 C10 1.388(8) . ?
C10 C11 1.381(8) . ?
C13 C14 1.487(8) . ?
C14 C15 1.570(9) . ?
C15 C16 1.531(8) . ?
C17 C18 1.388(8) . ?
C17 C22 1.391(8) . ?
C18 C19 1.385(8) . ?
C19 C20 1.392(8) . ?
C20 C21 1.384(8) . ?
C21 C22 1.374(8) . ?
