#------------------------------------------------------------------------------
#$Date: 2019-11-24 05:13:33 +0200 (Sun, 24 Nov 2019) $
#$Revision: 236806 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/08/74/4087458.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_4087458
loop_
_publ_author_name
'Engl, Pascal S.'
'Senn, Remo'
'Otth, Elisabeth'
'Togni, Antonio'
_publ_section_title
;
 Synthesis and Characterization of N-Trifluoromethyl N-Heterocyclic
 Carbene Ligands and Their Complexes
;
_journal_issue                   7
_journal_name_full               Organometallics
_journal_page_first              1384
_journal_paper_doi               10.1021/acs.organomet.5b00137
_journal_volume                  34
_journal_year                    2015
_chemical_formula_moiety         'C9 H7 Au Cl F3 N2'
_chemical_formula_sum            'C9 H7 Au Cl F3 N2'
_chemical_formula_weight         432.58
_chemical_melting_point          324
_space_group_crystal_system      monoclinic
_space_group_IT_number           11
_space_group_name_Hall           '-P 2yb'
_space_group_name_H-M_alt        'P 1 21/m 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2014-12-04
_audit_creation_method
;
Olex2 1.2
(compiled 2014.06.27 svn.r2953 for OlexSys, GUI svn.r4855)
;
_cell_angle_alpha                90
_cell_angle_beta                 108.303(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.0300(15)
_cell_length_b                   6.5561(11)
_cell_length_c                   9.5756(16)
_cell_measurement_reflns_used    3336
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.98
_cell_measurement_theta_min      2.24
_cell_volume                     538.21(16)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0612
_diffrn_reflns_av_unetI/netI     0.0456
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            10085
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.988
_diffrn_reflns_theta_min         2.240
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    13.927
_exptl_absorpt_correction_T_max  0.9978
_exptl_absorpt_correction_T_min  0.5362
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   'SADABS 2004/1'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.669
_exptl_crystal_description       plate
_exptl_crystal_F_000             396
_exptl_crystal_size_max          0.116
_exptl_crystal_size_mid          0.112
_exptl_crystal_size_min          0.048
_refine_diff_density_max         1.888
_refine_diff_density_min         -1.749
_refine_diff_density_rms         0.221
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     95
_refine_ls_number_reflns         1852
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.000
_refine_ls_R_factor_all          0.0337
_refine_ls_R_factor_gt           0.0264
_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)+(0.0272P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0545
_refine_ls_wR_factor_ref         0.0566
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1648
_reflns_number_total             1852
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            om5b00137_si_002.cif
_cod_data_source_block           Compound_9a
_cod_database_code               4087458
_shelxl_version_number           2013-4
_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.
;
_shelx_estimated_absorpt_t_max   0.555
_shelx_estimated_absorpt_t_min   0.295
_olex2_refinement_description
;
1. Others
 Fixed Sof: H9A(0.5) H9B(0.5) H9C(0.5)
 Fixed U12: Au1(0) Cl1(0) C1(0) C2(0) N1(0) F2(0) C5(0) C4(0) C3(0) N2(0)
 C8(0) C7(0) C9(0) C6(0)
 Fixed U23: Au1(0) Cl1(0) C1(0) C2(0) N1(0) F2(0) C5(0) C4(0) C3(0) N2(0)
 C8(0) C7(0) C9(0) C6(0)
 Fixed Uiso: H5(0.029) H4(0.022) H7(0.023) H9A(0.035) H9B(0.035) H9C(0.035)
 H6(0.032)
 Fixed X: H5(0.4505) H4(0.4324) H7(0.9223) H9A(1.1305) H9B(1.1151) H9C(1.1526)
 H6(0.6883)
 Fixed Y: Au1(0.25) Cl1(0.25) C1(0.25) C2(0.25) N1(0.25) F2(0.25) C5(0.25)
 H5(0.25) C4(0.25) H4(0.25) C3(0.25) N2(0.25) C8(0.25) C7(0.25) H7(0.25)
 C9(0.25) H9A(0.3902) H9B(0.1675) H9C(0.1923) C6(0.25) H6(0.25)
 Fixed Z: H5(-0.2246) H4(0.0155) H7(-0.0717) H9A(0.235) H9B(0.1634)
 H9C(0.3374) H6(-0.2653)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'
'-x, -y, -z'
'x, -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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
Au1 Au 0.98848(3) 0.2500 0.54488(2) 0.01389(7) Uani 1 2 d S T P
Cl1 Cl 1.13266(18) 0.2500 0.78736(14) 0.0178(3) Uani 1 2 d S T P
C1 C 0.8665(7) 0.2500 0.3329(6) 0.0157(11) Uani 1 2 d S T P
C2 C 0.6059(7) 0.2500 0.3538(6) 0.0207(12) Uani 1 2 d S T P
N1 N 0.7091(6) 0.2500 0.2687(5) 0.0143(9) Uani 1 2 d S T P
F2 F 0.4599(5) 0.2500 0.2675(4) 0.0295(9) Uani 1 2 d S T P
F1 F 0.6258(3) 0.0873(4) 0.4396(3) 0.0306(6) Uani 1 1 d . . .
C5 C 0.5430(8) 0.2500 -0.1426(7) 0.0242(13) Uani 1 2 d S T P
H5 H 0.4505 0.2500 -0.2246 0.029 Uiso 1 2 calc R U P
C4 C 0.5307(7) 0.2500 -0.0011(6) 0.0187(12) Uani 1 2 d S T P
H4 H 0.4324 0.2500 0.0155 0.022 Uiso 1 2 calc R U P
C3 C 0.6702(7) 0.2500 0.1144(6) 0.0154(11) Uani 1 2 d S T P
N2 N 0.9291(6) 0.2500 0.2226(5) 0.0153(9) Uani 1 2 d S T P
C8 C 0.8122(7) 0.2500 0.0882(6) 0.0166(11) Uani 1 2 d S T P
C7 C 0.8244(8) 0.2500 -0.0543(6) 0.0194(12) Uani 1 2 d S T P
H7 H 0.9223 0.2500 -0.0717 0.023 Uiso 1 2 calc R U P
C9 C 1.0954(7) 0.2500 0.2411(7) 0.0233(13) Uani 1 2 d S T P
H9A H 1.1305 0.3902 0.2350 0.035 Uiso 0.5 1 calc R U P
H9B H 1.1151 0.1675 0.1634 0.035 Uiso 0.5 1 calc R U P
H9C H 1.1526 0.1923 0.3374 0.035 Uiso 0.5 1 calc R U P
C6 C 0.6859(9) 0.2500 -0.1669(7) 0.0264(14) Uani 1 2 d S T P
H6 H 0.6883 0.2500 -0.2653 0.032 Uiso 1 2 calc R U P
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'
F F 0.0171 0.0103 '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
C1 Au1 Cl1 178.98(17) . .
N1 C1 Au1 129.0(4) . .
N2 C1 Au1 124.7(4) . .
N2 C1 N1 106.4(5) . .
F2 C2 N1 110.4(5) . .
F2 C2 F1 107.6(4) . 4_565
F2 C2 F1 107.6(4) . .
F1 C2 N1 111.8(3) 4_565 .
F1 C2 N1 111.8(3) . .
F1 C2 F1 107.3(5) 4_565 .
C1 N1 C2 121.5(5) . .
C1 N1 C3 110.8(5) . .
C3 N1 C2 127.7(5) . .
C6 C5 C4 121.8(6) . .
C3 C4 C5 116.4(6) . .
C4 C3 N1 134.4(6) . .
C8 C3 N1 104.5(5) . .
C8 C3 C4 121.0(5) . .
C1 N2 C8 110.1(5) . .
C1 N2 C9 125.2(5) . .
C8 N2 C9 124.7(5) . .
C3 C8 N2 108.2(5) . .
C3 C8 C7 122.5(6) . .
N2 C8 C7 129.3(6) . .
C6 C7 C8 115.7(6) . .
C7 C6 C5 122.5(6) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Au1 Cl1 2.2777(14) .
Au1 C1 1.982(6) .
C1 N1 1.360(8) .
C1 N2 1.346(7) .
C2 N1 1.417(7) .
C2 F2 1.318(7) .
C2 F1 1.324(4) .
C2 F1 1.324(4) 4_565
N1 C3 1.407(7) .
C5 C4 1.393(9) .
C5 C6 1.381(10) .
C4 C3 1.391(8) .
C3 C8 1.382(8) .
N2 C8 1.384(7) .
N2 C9 1.456(8) .
C8 C7 1.403(8) .
C7 C6 1.370(9) .
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
Au1 C1 N1 C2 0.000(1) .
Au1 C1 N1 C3 180.000(1) .
Au1 C1 N2 C8 180.000(1) .
Au1 C1 N2 C9 0.000(1) .
C1 N1 C3 C4 180.000(1) .
C1 N1 C3 C8 0.000(1) .
C1 N2 C8 C3 0.000(1) .
C1 N2 C8 C7 180.000(1) .
C2 N1 C3 C4 0.000(1) .
C2 N1 C3 C8 180.000(1) .
N1 C1 N2 C8 0.000(1) .
N1 C1 N2 C9 180.000(1) .
N1 C3 C8 N2 0.000(1) .
N1 C3 C8 C7 180.000(1) .
F2 C2 N1 C1 180.000(1) .
F2 C2 N1 C3 0.000(1) .
F1 C2 N1 C1 -60.2(4) .
F1 C2 N1 C1 60.2(4) 4_565
F1 C2 N1 C3 119.8(4) .
F1 C2 N1 C3 -119.8(4) 4_565
C5 C4 C3 N1 180.000(1) .
C5 C4 C3 C8 0.000(0) .
C4 C5 C6 C7 0.000(1) .
C4 C3 C8 N2 180.000(1) .
C4 C3 C8 C7 0.000(1) .
C3 C8 C7 C6 0.000(0) .
N2 C1 N1 C2 180.000(1) .
N2 C1 N1 C3 0.000(1) .
N2 C8 C7 C6 180.000(1) .
C8 C7 C6 C5 0.000(1) .
C9 N2 C8 C3 180.000(1) .
C9 N2 C8 C7 0.000(1) .
C6 C5 C4 C3 0.000(1) .
