#------------------------------------------------------------------------------
#$Date: 2017-07-11 14:26:40 +0300 (Tue, 11 Jul 2017) $
#$Revision: 198632 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/54/36/1543654.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_1543654
loop_
_publ_author_name
'Frutos, María'
'Avello, Marta G.'
'Viso, Alma'
'Fernández de la Pradilla, Roberto'
'de la Torre, María C'
'Sierra, Miguel A.'
'Gornitzka, Heinz'
'Hemmert, Catherine'
_publ_section_title
;
 Gold Sulfinyl Mesoionic Carbenes: Synthesis, Structure, and Catalytic
 Activity.
;
_journal_issue                   15
_journal_name_full               'Organic letters'
_journal_page_first              3570
_journal_page_last               3573
_journal_paper_doi               10.1021/acs.orglett.6b01555
_journal_volume                  18
_journal_year                    2016
_chemical_formula_sum            'C18 H19 Au Cl N3 O S'
_chemical_formula_weight         557.84
_chemical_name_systematic
; 
 ? 
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   10.9737(4)
_cell_length_b                   17.4658(7)
_cell_length_c                   19.9371(7)
_cell_measurement_reflns_used    9884
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.78
_cell_measurement_theta_min      2.19
_cell_volume                     3821.2(2)
_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-2014 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.986
_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  0.0795
_diffrn_reflns_av_unetI/netI     0.0756
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            39145
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.731
_diffrn_reflns_theta_min         5.097
_exptl_absorpt_coefficient_mu    7.960
_exptl_absorpt_correction_T_max  0.7459
_exptl_absorpt_correction_T_min  0.5952
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker-AXS)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.939
_exptl_crystal_description       block
_exptl_crystal_F_000             2144
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         3.896
_refine_diff_density_min         -3.426
_refine_diff_density_rms         0.265
_refine_ls_abs_structure_details
; 
 Flack x determined using 2663 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   -0.019(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     457
_refine_ls_number_reflns         7919
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.085
_refine_ls_R_factor_all          0.0649
_refine_ls_R_factor_gt           0.0498
_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)+(0.0118P)²+11.4607P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0607
_refine_ls_wR_factor_ref         0.0639
_reflns_Friedel_coverage         0.779
_reflns_Friedel_fraction_full    0.988
_reflns_Friedel_fraction_max     0.965
_reflns_number_gt                6845
_reflns_number_total             7919
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ol6b01555_si_004.cif
_cod_data_source_block           mfp660c_0m
_cod_depositor_comments
;Adding full bibliography for 1543653--1543655.cif.

The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'multi-scans' was replaced
with the value 'multi-scan' as specified in the replacement file
'src/cod-tools/trunk/data/replacement-values/replacement_values.lst'.

Automatic conversion script
Id: cif_fix_values 5376 2017-05-30 11:51:03Z andrius 
;
_cod_database_code               1543654
#BEGIN Tags that were not found in dictionaries:
_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. 
;
_shelxl_version_number           2014-3
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
Au1 Au 0.23467(3) 0.97122(2) 0.13640(2) 0.01479(11) Uani 1 1 d . .
Cl1 Cl 0.1206(2) 1.03145(16) 0.05727(15) 0.0264(6) Uani 1 1 d . .
Au2 Au 0.37998(4) 1.10234(2) 0.21728(2) 0.01565(11) Uani 1 1 d . .
Cl2 Cl 0.2022(2) 1.13919(15) 0.26707(17) 0.0302(8) Uani 1 1 d . .
C1 C 0.3446(9) 0.9169(5) 0.1998(6) 0.014(3) Uani 1 1 d . .
C2 C 0.4526(10) 0.8802(5) 0.1851(6) 0.014(2) Uani 1 1 d . .
N1 N 0.3352(8) 0.9085(5) 0.2668(5) 0.017(2) Uani 1 1 d . .
N2 N 0.4275(8) 0.8701(5) 0.2951(5) 0.016(2) Uani 1 1 d . .
N3 N 0.4975(9) 0.8530(5) 0.2432(6) 0.021(2) Uani 1 1 d . .
C3 C 0.2369(10) 0.9359(6) 0.3111(5) 0.018(3) Uani 1 1 d . .
H3 H 0.1897 0.9753 0.2856 0.022 Uiso 1 1 calc R U
C4 C 0.2902(10) 0.9756(6) 0.3730(6) 0.027(3) Uani 1 1 d . .
H4A H 0.3399 0.9390 0.3983 0.040 Uiso 1 1 calc R U
H4B H 0.2237 0.9943 0.4014 0.040 Uiso 1 1 calc R U
H4C H 0.3410 1.0188 0.3588 0.040 Uiso 1 1 calc R U
C5 C 0.1498(10) 0.8701(6) 0.3269(5) 0.016(3) Uani 1 1 d . .
C6 C 0.0302(10) 0.8732(7) 0.3046(6) 0.025(3) Uani 1 1 d . .
H6 H 0.0012 0.9171 0.2815 0.030 Uiso 1 1 calc R U
C7 C -0.0477(11) 0.8109(8) 0.3165(7) 0.036(4) Uani 1 1 d . .
H7 H -0.1292 0.8124 0.3003 0.043 Uiso 1 1 calc R U
C8 C -0.0075(10) 0.7481(7) 0.3510(6) 0.027(3) Uani 1 1 d . .
H8 H -0.0608 0.7061 0.3587 0.033 Uiso 1 1 calc R U
C9 C 0.1114(11) 0.7457(6) 0.3749(6) 0.025(3) Uani 1 1 d . .
H9 H 0.1393 0.7024 0.3994 0.030 Uiso 1 1 calc R U
C10 C 0.1890(9) 0.8067(6) 0.3629(6) 0.021(3) Uani 1 1 d . .
H10 H 0.2701 0.8051 0.3795 0.025 Uiso 1 1 calc R U
C11 C 0.6085(11) 0.8066(6) 0.2558(7) 0.032(3) Uani 1 1 d . .
H11A H 0.6259 0.8059 0.3040 0.047 Uiso 1 1 calc R U
H11B H 0.6776 0.8291 0.2317 0.047 Uiso 1 1 calc R U
H11C H 0.5952 0.7541 0.2399 0.047 Uiso 1 1 calc R U
S1 S 0.5236(3) 0.87678(15) 0.10456(16) 0.0216(7) Uani 1 1 d . .
O1 O 0.6575(6) 0.8747(4) 0.1156(4) 0.028(2) Uani 1 1 d . .
C12 C 0.4739(10) 0.7838(6) 0.0801(6) 0.018(3) Uani 1 1 d . .
C13 C 0.3567(10) 0.7766(6) 0.0536(6) 0.019(3) Uani 1 1 d . .
H13 H 0.3053 0.8201 0.0494 0.023 Uiso 1 1 calc R U
C14 C 0.3169(10) 0.7046(6) 0.0336(6) 0.021(3) Uani 1 1 d . .
H14 H 0.2370 0.6991 0.0159 0.025 Uiso 1 1 calc R U
C15 C 0.3913(10) 0.6405(6) 0.0389(6) 0.018(3) Uani 1 1 d . .
C16 C 0.5082(11) 0.6500(6) 0.0642(6) 0.026(3) Uani 1 1 d . .
H16 H 0.5608 0.6069 0.0671 0.032 Uiso 1 1 calc R U
C17 C 0.5499(11) 0.7211(6) 0.0854(6) 0.022(3) Uani 1 1 d . .
H17 H 0.6296 0.7265 0.1034 0.027 Uiso 1 1 calc R U
C18 C 0.3465(11) 0.5631(6) 0.0171(6) 0.024(3) Uani 1 1 d . .
H18A H 0.3039 0.5383 0.0545 0.036 Uiso 1 1 calc R U
H18B H 0.4159 0.5314 0.0034 0.036 Uiso 1 1 calc R U
H18C H 0.2904 0.5690 -0.0208 0.036 Uiso 1 1 calc R U
C19 C 0.5401(10) 1.0742(5) 0.1773(6) 0.016(3) Uani 1 1 d . .
C20 C 0.6480(9) 1.0533(5) 0.2082(6) 0.014(2) Uani 1 1 d . .
N4 N 0.5696(8) 1.0756(5) 0.1109(5) 0.014(2) Uani 1 1 d . .
N5 N 0.6867(8) 1.0582(5) 0.0987(5) 0.019(2) Uani 1 1 d . .
N6 N 0.7318(8) 1.0455(5) 0.1582(4) 0.015(2) Uani 1 1 d . .
C21 C 0.4844(9) 1.0927(6) 0.0551(5) 0.016(2) Uani 1 1 d . .
H21 H 0.4061 1.0655 0.0648 0.019 Uiso 1 1 calc R U
C22 C 0.5328(11) 1.0623(6) -0.0107(6) 0.024(3) Uani 1 1 d . .
H22A H 0.6105 1.0872 -0.0211 0.037 Uiso 1 1 calc R U
H22B H 0.4740 1.0730 -0.0465 0.037 Uiso 1 1 calc R U
H22C H 0.5452 1.0068 -0.0072 0.037 Uiso 1 1 calc R U
C23 C 0.4573(9) 1.1780(6) 0.0540(5) 0.013(2) Uani 1 1 d . .
C24 C 0.5486(10) 1.2305(6) 0.0388(6) 0.019(3) Uani 1 1 d . .
H24 H 0.6292 1.2131 0.0307 0.023 Uiso 1 1 calc R U
C25 C 0.5226(12) 1.3075(7) 0.0355(6) 0.028(3) Uani 1 1 d . .
H25 H 0.5847 1.3429 0.0237 0.034 Uiso 1 1 calc R U
C26 C 0.4059(12) 1.3336(6) 0.0495(6) 0.028(3) Uani 1 1 d . .
H26 H 0.3884 1.3868 0.0479 0.033 Uiso 1 1 calc R U
C27 C 0.3153(11) 1.2820(6) 0.0658(6) 0.023(3) Uani 1 1 d . .
H27 H 0.2357 1.2999 0.0761 0.028 Uiso 1 1 calc R U
C28 C 0.3397(10) 1.2049(6) 0.0674(6) 0.020(3) Uani 1 1 d . .
H28 H 0.2763 1.1697 0.0775 0.023 Uiso 1 1 calc R U
C29 C 0.8601(10) 1.0217(7) 0.1640(6) 0.028(3) Uani 1 1 d . .
H29A H 0.8641 0.9664 0.1720 0.043 Uiso 1 1 calc R U
H29B H 0.8984 1.0488 0.2015 0.043 Uiso 1 1 calc R U
H29C H 0.9033 1.0340 0.1223 0.043 Uiso 1 1 calc R U
S2 S 0.6697(2) 1.03468(16) 0.29414(15) 0.0200(6) Uani 1 1 d . .
O2 O 0.7360(7) 0.9602(4) 0.3000(4) 0.0284(19) Uani 1 1 d . .
C30 C 0.7781(9) 1.1087(6) 0.3116(5) 0.017(2) Uani 1 1 d . .
C31 C 0.8810(10) 1.0896(6) 0.3492(5) 0.020(3) Uani 1 1 d . .
H31 H 0.8960 1.0380 0.3617 0.024 Uiso 1 1 calc R U
C32 C 0.9603(10) 1.1467(6) 0.3680(7) 0.023(3) Uani 1 1 d . .
H32 H 1.0306 1.1340 0.3935 0.027 Uiso 1 1 calc R U
C33 C 0.9397(10) 1.2232(6) 0.3502(6) 0.020(3) Uani 1 1 d . .
C34 C 0.8363(10) 1.2401(6) 0.3138(6) 0.023(3) Uani 1 1 d . .
H34 H 0.8204 1.2919 0.3021 0.028 Uiso 1 1 calc R U
C35 C 0.7554(10) 1.1845(6) 0.2940(5) 0.019(2) Uani 1 1 d . .
H35 H 0.6851 1.1976 0.2687 0.023 Uiso 1 1 calc R U
C36 C 1.0267(11) 1.2850(7) 0.3711(7) 0.033(3) Uani 1 1 d . .
H36A H 1.0976 1.2847 0.3412 0.050 Uiso 1 1 calc R U
H36B H 1.0534 1.2758 0.4173 0.050 Uiso 1 1 calc R U
H36C H 0.9860 1.3348 0.3684 0.050 Uiso 1 1 calc R U
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'
Au Au -2.0133 8.8022 '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'
O O 0.0106 0.0060 '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_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C1 Au1 Cl1 175.3(3)
C1 Au1 Au2 73.8(3)
Cl1 Au1 Au2 106.92(7)
C19 Au2 Cl2 176.8(3)
C19 Au2 Au1 93.5(3)
Cl2 Au2 Au1 89.72(8)
N1 C1 C2 103.1(9)
N1 C1 Au1 129.4(8)
C2 C1 Au1 127.5(8)
N3 C2 C1 107.2(10)
N3 C2 S1 127.0(8)
C1 C2 S1 125.6(9)
N2 N1 C1 114.5(9)
N2 N1 C3 117.5(9)
C1 N1 C3 128.0(9)
N3 N2 N1 102.8(8)
N2 N3 C2 112.4(9)
N2 N3 C11 117.8(10)
C2 N3 C11 129.7(10)
N1 C3 C5 109.6(8)
N1 C3 C4 110.6(9)
C5 C3 C4 114.4(9)
C6 C5 C10 119.3(10)
C6 C5 C3 119.9(10)
C10 C5 C3 120.8(9)
C5 C6 C7 119.6(11)
C8 C7 C6 120.6(11)
C7 C8 C9 120.0(11)
C10 C9 C8 119.6(11)
C9 C10 C5 120.9(10)
O1 S1 C12 108.7(5)
O1 S1 C2 107.4(5)
C12 S1 C2 98.3(5)
C17 C12 C13 121.0(10)
C17 C12 S1 121.1(9)
C13 C12 S1 117.8(8)
C14 C13 C12 118.6(10)
C15 C14 C13 121.4(10)
C16 C15 C14 118.4(10)
C16 C15 C18 120.9(10)
C14 C15 C18 120.7(10)
C15 C16 C17 121.4(11)
C12 C17 C16 119.1(11)
N4 C19 C20 103.6(9)
N4 C19 Au2 126.5(8)
C20 C19 Au2 129.9(9)
N6 C20 C19 106.1(10)
N6 C20 S2 127.0(8)
C19 C20 S2 126.8(9)
N5 N4 C19 113.6(9)
N5 N4 C21 120.8(9)
C19 N4 C21 125.6(9)
N6 N5 N4 103.7(9)
N5 N6 C20 113.1(9)
N5 N6 C29 118.9(8)
C20 N6 C29 128.0(9)
N4 C21 C22 111.0(9)
N4 C21 C23 109.4(8)
C22 C21 C23 113.6(9)
C24 C23 C28 118.9(9)
C24 C23 C21 120.6(10)
C28 C23 C21 120.5(9)
C25 C24 C23 120.3(11)
C24 C25 C26 120.2(11)
C27 C26 C25 119.9(10)
C28 C27 C26 120.3(11)
C27 C28 C23 120.3(10)
O2 S2 C20 107.6(4)
O2 S2 C30 106.9(5)
C20 S2 C30 98.4(5)
C35 C30 C31 120.5(10)
C35 C30 S2 121.3(8)
C31 C30 S2 118.0(8)
C32 C31 C30 119.0(10)
C31 C32 C33 121.3(11)
C34 C33 C32 118.1(10)
C34 C33 C36 121.1(10)
C32 C33 C36 120.8(11)
C35 C34 C33 122.1(10)
C34 C35 C30 119.0(10)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Au1 C1 1.988(11)
Au1 Cl1 2.272(3)
Au1 Au2 3.2230(6)
Au2 C19 1.991(11)
Au2 Cl2 2.282(3)
C1 N1 1.348(14)
C1 C2 1.378(14)
C2 N3 1.346(14)
C2 S1 1.785(12)
N1 N2 1.340(11)
N1 C3 1.475(13)
N2 N3 1.324(13)
N3 C11 1.484(14)
C3 C5 1.528(14)
C3 C4 1.530(15)
C5 C6 1.386(15)
C5 C10 1.389(15)
C6 C7 1.403(17)
C7 C8 1.369(17)
C8 C9 1.389(16)
C9 C10 1.385(14)
S1 O1 1.486(8)
S1 C12 1.782(11)
C12 C17 1.380(15)
C12 C13 1.395(15)
C13 C14 1.391(14)
C14 C15 1.389(15)
C15 C16 1.389(16)
C15 C18 1.504(14)
C16 C17 1.390(15)
C19 N4 1.362(14)
C19 C20 1.384(14)
C20 N6 1.365(13)
C20 S2 1.760(12)
N4 N5 1.343(11)
N4 C21 1.484(13)
N5 N6 1.304(12)
N6 C29 1.472(13)
C21 C22 1.512(15)
C21 C23 1.519(14)
C23 C24 1.391(14)
C23 C28 1.400(15)
C24 C25 1.377(15)
C25 C26 1.387(17)
C26 C27 1.380(16)
C27 C28 1.373(15)
S2 O2 1.494(7)
S2 C30 1.791(11)
C30 C35 1.392(13)
C30 C31 1.396(14)
C31 C32 1.375(15)
C32 C33 1.401(15)
C33 C34 1.378(15)
C33 C36 1.500(15)
C34 C35 1.373(15)
