#------------------------------------------------------------------------------
#$Date: 2017-07-11 14:26:40 +0300 (Tue, 11 Jul 2017) $
#$Revision: 198632 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/54/36/1543653.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_1543653
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            4
_cell_length_a                   7.5537(2)
_cell_length_b                   14.1240(5)
_cell_length_c                   18.0020(6)
_cell_measurement_reflns_used    9953
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      32.92
_cell_measurement_theta_min      2.68
_cell_volume                     1920.61(11)
_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 0.989
_diffrn_measured_fraction_theta_max 0.992
_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  0.0208
_diffrn_reflns_av_unetI/netI     0.0170
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            19840
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.281
_diffrn_reflns_theta_min         5.103
_exptl_absorpt_coefficient_mu    7.918
_exptl_absorpt_correction_T_max  0.7465
_exptl_absorpt_correction_T_min  0.5276
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker-AXS)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.929
_exptl_crystal_description       block
_exptl_crystal_F_000             1072
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.302
_refine_diff_density_min         -0.256
_refine_diff_density_rms         0.052
_refine_ls_abs_structure_details
; 
 Flack x determined using 1997 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   -0.019(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         4737
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0108
_refine_ls_R_factor_gt           0.0104
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0096P)²+0.2787P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0240
_refine_ls_wR_factor_ref         0.0241
_reflns_Friedel_coverage         0.759
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                4656
_reflns_number_total             4737
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ol6b01555_si_003.cif
_cod_data_source_block           mfp821m
_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               1543653
#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 0.44093(2) 0.77811(2) 0.45109(2) 0.01573(3) Uani 1 1 d . .
Cl1 Cl 0.44009(10) 0.86118(4) 0.34238(3) 0.02501(13) Uani 1 1 d . .
C1 C 0.4557(3) 0.70562(16) 0.54500(14) 0.0163(4) Uani 1 1 d . .
C2 C 0.4979(3) 0.61254(17) 0.55897(14) 0.0168(5) Uani 1 1 d . .
N1 N 0.5067(3) 0.60098(15) 0.63435(12) 0.0182(5) Uani 1 1 d . .
N2 N 0.4704(3) 0.68004(15) 0.66917(12) 0.0191(5) Uani 1 1 d . .
N3 N 0.4389(3) 0.74185(14) 0.61521(11) 0.0164(4) Uani 1 1 d . .
C3 C 0.5571(5) 0.51731(18) 0.67710(14) 0.0253(6) Uani 1 1 d . .
H3A H 0.5851 0.5360 0.7282 0.038 Uiso 1 1 calc R U
H3B H 0.6612 0.4878 0.6544 0.038 Uiso 1 1 calc R U
H3C H 0.4587 0.4721 0.6774 0.038 Uiso 1 1 calc R U
S1 S 0.52831(10) 0.52332(4) 0.49048(4) 0.02210(14) Uani 1 1 d . .
O1 O 0.7104(3) 0.48375(14) 0.49641(13) 0.0345(5) Uani 1 1 d . .
C4 C 0.3830(3) 0.43734(17) 0.53135(14) 0.0167(5) Uani 1 1 d . .
C5 C 0.4495(4) 0.34769(17) 0.54565(15) 0.0247(5) Uani 1 1 d . .
H5 H 0.5688 0.3323 0.5340 0.030 Uiso 1 1 calc R U
C6 C 0.3379(4) 0.2808(2) 0.57746(15) 0.0302(6) Uani 1 1 d . .
H6 H 0.3820 0.2191 0.5875 0.036 Uiso 1 1 calc R U
C7 C 0.1649(4) 0.3019(2) 0.59470(16) 0.0307(7) Uani 1 1 d . .
C8 C 0.1000(4) 0.3912(2) 0.57785(16) 0.0273(7) Uani 1 1 d . .
H8 H -0.0203 0.4057 0.5882 0.033 Uiso 1 1 calc R U
C9 C 0.2079(3) 0.45969(18) 0.54615(16) 0.0213(5) Uani 1 1 d . .
H9 H 0.1626 0.5207 0.5348 0.026 Uiso 1 1 calc R U
C10 C 0.0494(6) 0.2291(3) 0.63295(18) 0.0503(10) Uani 1 1 d . .
H10A H 0.0901 0.1654 0.6199 0.075 Uiso 1 1 calc R U
H10B H -0.0736 0.2372 0.6169 0.075 Uiso 1 1 calc R U
H10C H 0.0569 0.2377 0.6869 0.075 Uiso 1 1 calc R U
C11 C 0.3885(3) 0.84000(19) 0.63503(16) 0.0197(5) Uani 1 1 d . .
H11 H 0.3251 0.8682 0.5916 0.024 Uiso 1 1 calc R U
C12 C 0.2605(4) 0.8386(2) 0.70062(19) 0.0332(7) Uani 1 1 d . .
H12A H 0.1610 0.7965 0.6893 0.050 Uiso 1 1 calc R U
H12B H 0.2161 0.9028 0.7097 0.050 Uiso 1 1 calc R U
H12C H 0.3222 0.8156 0.7450 0.050 Uiso 1 1 calc R U
C13 C 0.5479(3) 0.90137(16) 0.65176(13) 0.0145(4) Uani 1 1 d . .
C14 C 0.5454(4) 0.99437(18) 0.62631(14) 0.0197(5) Uani 1 1 d . .
H14 H 0.4534 1.0151 0.5942 0.024 Uiso 1 1 calc R U
C15 C 0.6784(4) 1.05711(19) 0.64800(16) 0.0237(6) Uani 1 1 d . .
H15 H 0.6771 1.1205 0.6304 0.028 Uiso 1 1 calc R U
C16 C 0.8117(4) 1.0274(2) 0.69484(15) 0.0230(6) Uani 1 1 d . .
H16 H 0.9007 1.0706 0.7104 0.028 Uiso 1 1 calc R U
C17 C 0.8155(4) 0.93446(19) 0.71918(14) 0.0194(5) Uani 1 1 d . .
H17 H 0.9083 0.9139 0.7509 0.023 Uiso 1 1 calc R U
C18 C 0.6850(3) 0.87107(18) 0.69769(14) 0.0176(5) Uani 1 1 d . .
H18 H 0.6890 0.8072 0.7142 0.021 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'
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'
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
C1 Au1 Cl1 176.92(7)
N3 C1 C2 102.1(2)
N3 C1 Au1 126.13(16)
C2 C1 Au1 131.55(19)
N1 C2 C1 107.9(2)
N1 C2 S1 126.64(19)
C1 C2 S1 125.5(2)
N2 N1 C2 111.3(2)
N2 N1 C3 119.5(2)
C2 N1 C3 129.2(2)
N1 N2 N3 104.37(19)
N2 N3 C1 114.39(19)
N2 N3 C11 119.0(2)
C1 N3 C11 126.6(2)
N1 C3 H3A 109.5
N1 C3 H3B 109.5
H3A C3 H3B 109.5
N1 C3 H3C 109.5
H3A C3 H3C 109.5
H3B C3 H3C 109.5
O1 S1 C2 109.63(12)
O1 S1 C4 106.37(12)
C2 S1 C4 96.67(11)
C9 C4 C5 121.2(2)
C9 C4 S1 120.6(2)
C5 C4 S1 118.2(2)
C4 C5 C6 118.5(3)
C4 C5 H5 120.7
C6 C5 H5 120.7
C7 C6 C5 121.4(3)
C7 C6 H6 119.3
C5 C6 H6 119.3
C6 C7 C8 118.9(3)
C6 C7 C10 120.2(3)
C8 C7 C10 120.9(3)
C7 C8 C9 121.1(3)
C7 C8 H8 119.4
C9 C8 H8 119.4
C4 C9 C8 118.7(3)
C4 C9 H9 120.6
C8 C9 H9 120.6
C7 C10 H10A 109.5
C7 C10 H10B 109.5
H10A C10 H10B 109.5
C7 C10 H10C 109.5
H10A C10 H10C 109.5
H10B C10 H10C 109.5
N3 C11 C13 112.26(19)
N3 C11 C12 109.7(2)
C13 C11 C12 110.9(2)
N3 C11 H11 107.9
C13 C11 H11 107.9
C12 C11 H11 107.9
C11 C12 H12A 109.5
C11 C12 H12B 109.5
H12A C12 H12B 109.5
C11 C12 H12C 109.5
H12A C12 H12C 109.5
H12B C12 H12C 109.5
C14 C13 C18 119.7(2)
C14 C13 C11 117.7(2)
C18 C13 C11 122.3(2)
C13 C14 C15 119.9(2)
C13 C14 H14 120.1
C15 C14 H14 120.1
C16 C15 C14 120.2(2)
C16 C15 H15 119.9
C14 C15 H15 119.9
C15 C16 C17 119.8(3)
C15 C16 H16 120.1
C17 C16 H16 120.1
C16 C17 C18 120.6(3)
C16 C17 H17 119.7
C18 C17 H17 119.7
C17 C18 C13 119.7(2)
C17 C18 H18 120.1
C13 C18 H18 120.1
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Au1 C1 1.980(2)
Au1 Cl1 2.2817(6)
C1 N3 1.370(3)
C1 C2 1.376(3)
C2 N1 1.368(3)
C2 S1 1.778(3)
N1 N2 1.310(3)
N1 C3 1.461(3)
N2 N3 1.327(3)
N3 C11 1.481(3)
C3 H3A 0.9800
C3 H3B 0.9800
C3 H3C 0.9800
S1 O1 1.489(2)
S1 C4 1.795(3)
C4 C9 1.385(4)
C4 C5 1.387(3)
C5 C6 1.390(4)
C5 H5 0.9500
C6 C7 1.376(5)
C6 H6 0.9500
C7 C8 1.387(5)
C7 C10 1.514(4)
C8 C9 1.388(4)
C8 H8 0.9500
C9 H9 0.9500
C10 H10A 0.9800
C10 H10B 0.9800
C10 H10C 0.9800
C11 C13 1.514(3)
C11 C12 1.526(4)
C11 H11 1.0000
C12 H12A 0.9800
C12 H12B 0.9800
C12 H12C 0.9800
C13 C14 1.391(3)
C13 C18 1.392(4)
C14 C15 1.395(4)
C14 H14 0.9500
C15 C16 1.379(4)
C15 H15 0.9500
C16 C17 1.384(4)
C16 H16 0.9500
C17 C18 1.387(4)
C17 H17 0.9500
C18 H18 0.9500
