#------------------------------------------------------------------------------
#$Date: 2023-04-20 14:53:48 +0300 (Thu, 20 Apr 2023) $
#$Revision: 282777 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/10/08/1100865.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_1100865
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            'C23 H32 Au Cl N2'
_chemical_formula_weight         568.92
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 111.4490(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.5735(7)
_cell_length_b                   11.7626(6)
_cell_length_c                   12.9098(6)
_cell_measurement_reflns_used    28583
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      30.466
_cell_measurement_theta_min      2.292
_cell_volume                     2059.76(17)
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean ?
_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  0.0364
_diffrn_reflns_av_sigmaI/netI    0.0230
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            32039
_diffrn_reflns_theta_full        30.47
_diffrn_reflns_theta_max         30.47
_diffrn_reflns_theta_min         2.29
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_exptl_absorpt_coefficient_mu    7.283
_exptl_absorpt_correction_T_max  1.000000
_exptl_absorpt_correction_T_min  0.287418
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.835
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1120
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_refine_diff_density_max         2.094
_refine_diff_density_min         -1.338
_refine_diff_density_rms         0.115
_refine_ls_extinction_coef       0.00428(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         6242
_refine_ls_number_restraints     273
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.0225
_refine_ls_R_factor_gt           0.0207
_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)+(0.0203P)²+3.4771P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0524
_refine_ls_wR_factor_ref         0.0535
_reflns_number_gt                5883
_reflns_number_total             6242
_reflns_threshold_expression     >2sigma(I)
_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 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               1100865
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
Au1 Au 0.195987(6) 0.052787(7) 0.361363(6) 0.01650(4) Uani 1 1 d U . .
Cl1 Cl 0.23231(5) -0.04848(5) 0.52166(5) 0.02295(11) Uani 1 1 d U . .
C4 C -0.02174(16) 0.1305(2) 0.14926(19) 0.0175(4) Uani 1 1 d U . .
N1 N 0.07522(14) 0.16829(17) 0.14611(16) 0.0172(3) Uani 1 1 d U . .
N2 N 0.23134(14) 0.20234(17) 0.19072(16) 0.0170(3) Uani 1 1 d U . .
C12 C -0.02789(17) 0.0004(2) 0.14720(19) 0.0191(4) Uani 1 1 d U . .
H12A H 0.0259 -0.0313 0.2124 0.023 Uiso 1 1 calc R . .
H12B H -0.0202 -0.0289 0.0789 0.023 Uiso 1 1 calc R . .
C13 C -0.12866(19) -0.0366(2) 0.1498(2) 0.0216(4) Uani 1 1 d U . .
H13 H -0.1326 -0.1215 0.1490 0.026 Uiso 1 1 calc R . .
C7 C -0.21069(19) 0.0109(2) 0.0474(2) 0.0262(5) Uani 1 1 d U . .
H7A H -0.2757 -0.0141 0.0469 0.031 Uiso 1 1 calc R . .
H7B H -0.2030 -0.0177 -0.0211 0.031 Uiso 1 1 calc R . .
C6 C -0.20481(18) 0.1412(2) 0.0507(2) 0.0255(5) Uani 1 1 d U . .
H6 H -0.2587 0.1726 -0.0161 0.031 Uiso 1 1 calc R . .
C8 C -0.2172(2) 0.1861(2) 0.1554(3) 0.0295(5) Uani 1 1 d U . .
H8A H -0.2818 0.1621 0.1568 0.035 Uiso 1 1 calc R . .
H8B H -0.2148 0.2702 0.1562 0.035 Uiso 1 1 calc R . .
C9 C -0.13364(19) 0.1387(2) 0.2578(2) 0.0254(5) Uani 1 1 d U . .
H9 H -0.1411 0.1679 0.3271 0.030 Uiso 1 1 calc R . .
C10 C -0.13785(19) 0.0085(2) 0.2569(2) 0.0250(5) Uani 1 1 d U . .
H10A H -0.0835 -0.0219 0.3224 0.030 Uiso 1 1 calc R . .
H10B H -0.2010 -0.0170 0.2614 0.030 Uiso 1 1 calc R . .
C11 C -0.03412(18) 0.1771(2) 0.2549(2) 0.0214(4) Uani 1 1 d U . .
H11A H 0.0200 0.1486 0.3218 0.026 Uiso 1 1 calc R . .
H11B H -0.0309 0.2611 0.2552 0.026 Uiso 1 1 calc R . .
C5 C -0.10501(17) 0.1784(2) 0.0477(2) 0.0219(4) Uani 1 1 d U . .
H5A H -0.0980 0.1503 -0.0214 0.026 Uiso 1 1 calc R . .
H5B H -0.1012 0.2624 0.0480 0.026 Uiso 1 1 calc R . .
C1 C 0.16563(16) 0.14601(19) 0.22436(18) 0.0175(4) Uani 1 1 d U . .
C2 C 0.08535(17) 0.2382(2) 0.06427(19) 0.0208(4) Uani 1 1 d U . .
H2 H 0.0334 0.2660 0.0005 0.025 Uiso 1 1 calc R . .
C3 C 0.18193(17) 0.2592(2) 0.09174(19) 0.0205(4) Uani 1 1 d U . .
H3 H 0.2110 0.3045 0.0510 0.025 Uiso 1 1 calc R . .
C15 C 0.33924(16) 0.21345(19) 0.25489(18) 0.0166(4) Uani 1 1 d U . .
C23 C 0.39011(17) 0.0967(2) 0.2761(2) 0.0195(4) Uani 1 1 d U . .
H23A H 0.3600 0.0475 0.3173 0.023 Uiso 1 1 calc R . .
H23B H 0.3811 0.0595 0.2043 0.023 Uiso 1 1 calc R . .
C20 C 0.50048(17) 0.1113(2) 0.3440(2) 0.0215(4) Uani 1 1 d U . .
H20 H 0.5331 0.0351 0.3587 0.026 Uiso 1 1 calc R . .
C21 C 0.51430(18) 0.1699(2) 0.4553(2) 0.0240(5) Uani 1 1 d U . .
H21A H 0.4843 0.1229 0.4982 0.029 Uiso 1 1 calc R . .
H21B H 0.5855 0.1782 0.4999 0.029 Uiso 1 1 calc R . .
C22 C 0.46526(18) 0.2874(2) 0.4330(2) 0.0234(4) Uani 1 1 d U . .
H22 H 0.4747 0.3255 0.5054 0.028 Uiso 1 1 calc R . .
C18 C 0.51118(19) 0.3607(2) 0.3664(2) 0.0262(5) Uani 1 1 d U . .
H18A H 0.4791 0.4362 0.3517 0.031 Uiso 1 1 calc R . .
H18B H 0.5823 0.3718 0.4096 0.031 Uiso 1 1 calc R . .
C17 C 0.49721(17) 0.3012(2) 0.2564(2) 0.0231(5) Uani 1 1 d U . .
H17 H 0.5274 0.3486 0.2129 0.028 Uiso 1 1 calc R . .
C19 C 0.54744(18) 0.1849(2) 0.2792(2) 0.0240(5) Uani 1 1 d U . .
H19A H 0.5401 0.1474 0.2079 0.029 Uiso 1 1 calc R . .
H19B H 0.6187 0.1943 0.3228 0.029 Uiso 1 1 calc R . .
C16 C 0.38644(17) 0.2866(2) 0.1888(2) 0.0214(4) Uani 1 1 d U . .
H16A H 0.3771 0.2494 0.1169 0.026 Uiso 1 1 calc R . .
H16B H 0.3541 0.3620 0.1733 0.026 Uiso 1 1 calc R . .
C24 C 0.35473(17) 0.2732(2) 0.36595(19) 0.0203(4) Uani 1 1 d U . .
H24A H 0.3225 0.3487 0.3515 0.024 Uiso 1 1 calc R . .
H24B H 0.3242 0.2276 0.4093 0.024 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 178.07(7) . . ?
N1 C4 C12 110.27(18) . . ?
N1 C4 C5 109.13(18) . . ?
C12 C4 C5 109.24(19) . . ?
N1 C4 C11 109.62(18) . . ?
C12 C4 C11 110.22(18) . . ?
C5 C4 C11 108.33(19) . . ?
C1 N1 C2 109.59(19) . . ?
C1 N1 C4 126.18(19) . . ?
C2 N1 C4 124.13(19) . . ?
C1 N2 C3 109.88(19) . . ?
C1 N2 C15 126.02(18) . . ?
C3 N2 C15 123.79(19) . . ?
C4 C12 C13 109.36(19) . . ?
C7 C13 C10 110.8(2) . . ?
C7 C13 C12 109.1(2) . . ?
C10 C13 C12 108.7(2) . . ?
C13 C7 C6 108.9(2) . . ?
C8 C6 C5 110.2(2) . . ?
C8 C6 C7 110.3(2) . . ?
C5 C6 C7 109.2(2) . . ?
C6 C8 C9 108.9(2) . . ?
C10 C9 C11 109.3(2) . . ?
C10 C9 C8 109.8(2) . . ?
C11 C9 C8 109.3(2) . . ?
C13 C10 C9 109.7(2) . . ?
C9 C11 C4 109.6(2) . . ?
C4 C5 C6 109.60(19) . . ?
N2 C1 N1 105.84(19) . . ?
N2 C1 Au1 126.81(16) . . ?
N1 C1 Au1 127.34(16) . . ?
C3 C2 N1 107.5(2) . . ?
C2 C3 N2 107.2(2) . . ?
N2 C15 C24 108.88(17) . . ?
N2 C15 C23 111.26(18) . . ?
C24 C15 C23 110.18(18) . . ?
N2 C15 C16 109.59(18) . . ?
C24 C15 C16 108.57(19) . . ?
C23 C15 C16 108.30(18) . . ?
C20 C23 C15 109.75(19) . . ?
C19 C20 C23 109.7(2) . . ?
C19 C20 C21 109.0(2) . . ?
C23 C20 C21 109.61(19) . . ?
C22 C21 C20 109.56(19) . . ?
C24 C22 C18 109.2(2) . . ?
C24 C22 C21 109.2(2) . . ?
C18 C22 C21 110.1(2) . . ?
C17 C18 C22 109.0(2) . . ?
C18 C17 C19 109.8(2) . . ?
C18 C17 C16 109.5(2) . . ?
C19 C17 C16 109.8(2) . . ?
C20 C19 C17 109.5(2) . . ?
C17 C16 C15 109.71(19) . . ?
C22 C24 C15 109.99(19) . . ?
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 1.989(2) . ?
Au1 Cl1 2.2761(6) . ?
C4 N1 1.496(3) . ?
C4 C12 1.532(3) . ?
C4 C5 1.532(3) . ?
C4 C11 1.541(3) . ?
N1 C1 1.361(3) . ?
N1 C2 1.388(3) . ?
N2 C1 1.360(3) . ?
N2 C3 1.388(3) . ?
N2 C15 1.491(3) . ?
C12 C13 1.544(3) . ?
C13 C7 1.528(4) . ?
C13 C10 1.532(4) . ?
C7 C6 1.534(4) . ?
C6 C8 1.522(4) . ?
C6 C5 1.533(3) . ?
C8 C9 1.537(4) . ?
C9 C10 1.532(4) . ?
C9 C11 1.533(3) . ?
C2 C3 1.343(3) . ?
C15 C24 1.537(3) . ?
C15 C23 1.537(3) . ?
C15 C16 1.539(3) . ?
C23 C20 1.534(3) . ?
C20 C19 1.529(3) . ?
C20 C21 1.539(4) . ?
C21 C22 1.533(4) . ?
C22 C24 1.534(3) . ?
C22 C18 1.533(4) . ?
C18 C17 1.529(4) . ?
C17 C19 1.528(4) . ?
C17 C16 1.538(3) . ?
