#------------------------------------------------------------------------------
#$Date: 2024-08-01 02:08:24 +0200 (Thu 01 de Aug de 2024) $
#$Revision: 293611 $
#$URL: svn://www.crystallography.net/cod/cif/7/24/91/7249154.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_7249154
loop_
_publ_author_name
'Mahdavi, Seyedehmahbobeh'
'Bockfeld, Dirk'
'Esarev, Igor V.'
'Lippmann, Petra'
'Frank, René'
'Brönstrup, Mark'
'Ott, Ingo'
'Tamm, Matthias'
_publ_section_title
;
 Gold(I) and Gold(III) Carbene Complexes from the Marine Betaine
 Norzooanemonin: Inhibition of Thioredoxin Reductase, Anti-proliferative
 and Antimicrobial Activity
;
_journal_name_full               'RSC Medicinal Chemistry'
_journal_paper_doi               10.1039/D4MD00358F
_journal_year                    2024
_chemical_formula_moiety         'C8 H12 Au Cl N2 O2'
_chemical_formula_sum            'C8 H12 Au Cl N2 O2'
_chemical_formula_weight         400.61
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2024-05-14 deposited with the CCDC.	2024-07-30 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.314(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   17.5275(4)
_cell_length_b                   7.06271(17)
_cell_length_c                   17.9398(4)
_cell_measurement_reflns_used    39118
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      38.5740
_cell_measurement_theta_min      2.2710
_cell_volume                     2207.33(9)
_computing_cell_refinement       'CrysAlisPro 1.171.42.64a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.64a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.64a (Rigaku OD, 2022)'
_computing_publication_material
'OLEX2 v1.3 (O. V. Dolomanov et al., J. Appl. Cryst., 2009, 42, 339-341)'
_computing_structure_refinement
'SHELXL-2018/3 (G. M. Sheldrick, Acta Cryst., 2015, C71, 3-8)'
_computing_structure_solution
'SHELXT 2018/2 (G. M. Sheldrick, Acta Cryst., 2015, A71, 3-8)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.959
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'XtaLAB Synergy, Single source at offset/far, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0404
_diffrn_reflns_av_unetI/netI     0.0260
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.959
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            114486
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.959
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         38.264
_diffrn_reflns_theta_min         2.284
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    13.548
_exptl_absorpt_correction_T_max  0.794
_exptl_absorpt_correction_T_min  0.413
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.64a (Rigaku Oxford Diffraction, 2022)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.411
_exptl_crystal_description       irregular
_exptl_crystal_F_000             1488
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.090
_exptl_crystal_size_min          0.040
_refine_diff_density_max         1.755
_refine_diff_density_min         -1.499
_refine_diff_density_rms         0.172
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     259
_refine_ls_number_reflns         11729
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0405
_refine_ls_R_factor_gt           0.0262
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0156P)²+2.6447P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0435
_refine_ls_wR_factor_ref         0.0460
_reflns_Friedel_coverage         0.000
_reflns_number_gt                9559
_reflns_number_total             11729
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4md00358f2.cif
_cod_data_source_block           sm24db
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7249154
_shelx_shelxl_version_number     2018/3
_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_min   0.344
_shelx_estimated_absorpt_t_max   0.613
_oxdiff_exptl_absorpt_empirical_full_min 0.893
_oxdiff_exptl_absorpt_empirical_full_max 1.126
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Au1 Au 0.26272(2) 0.15869(2) 0.48331(2) 0.01499(2) Uani 1 1 d . . . . .
Cl1 Cl 0.36861(3) 0.14830(8) 0.41942(3) 0.02042(10) Uani 1 1 d . . . . .
O1 O 0.09886(10) 0.0713(2) 0.75363(9) 0.0230(3) Uani 1 1 d . . . . .
O2 O -0.01790(9) 0.1025(2) 0.68839(9) 0.0192(3) Uani 1 1 d . . . . .
N1 N 0.09770(10) 0.2118(2) 0.50589(10) 0.0144(3) Uani 1 1 d . . . . .
N2 N 0.16274(10) 0.1195(2) 0.60839(10) 0.0149(3) Uani 1 1 d . . . . .
C1 C 0.16909(12) 0.1662(3) 0.53609(11) 0.0152(3) Uani 1 1 d . . . . .
C2 C 0.04622(12) 0.1938(3) 0.55738(11) 0.0157(3) Uani 1 1 d . . . . .
H2 H -0.007342 0.218389 0.549356 0.019 Uiso 1 1 calc R U . . .
C3 C 0.08647(11) 0.1338(3) 0.62256(11) 0.0144(3) Uani 1 1 d . . . . .
C4 C 0.07872(13) 0.2808(3) 0.42940(12) 0.0189(4) Uani 1 1 d . . . . .
H4A H 0.106711 0.398584 0.422699 0.028 Uiso 1 1 calc R U . . .
H4B H 0.023395 0.304603 0.420277 0.028 Uiso 1 1 calc R U . . .
H4C H 0.093301 0.185487 0.393874 0.028 Uiso 1 1 calc R U . . .
C5 C 0.22541(13) 0.0463(3) 0.66077(13) 0.0208(4) Uani 1 1 d . . . . .
H5A H 0.273342 0.050671 0.637387 0.031 Uiso 1 1 calc R U . . .
H5B H 0.214327 -0.084817 0.673802 0.031 Uiso 1 1 calc R U . . .
H5C H 0.230634 0.124046 0.706304 0.031 Uiso 1 1 calc R U . . .
C6 C 0.05902(13) 0.0986(3) 0.69548(12) 0.0167(4) Uani 1 1 d . . . . .
C7 C -0.05335(13) 0.0839(3) 0.75754(13) 0.0203(4) Uani 1 1 d . . . . .
H7A H -0.042515 0.197397 0.789350 0.024 Uiso 1 1 calc R U . . .
H7B H -0.032799 -0.028595 0.785914 0.024 Uiso 1 1 calc R U . . .
C8 C -0.13865(15) 0.0632(4) 0.73632(15) 0.0288(5) Uani 1 1 d . . . . .
H8A H -0.148983 -0.055606 0.708802 0.043 Uiso 1 1 calc R U . . .
H8B H -0.157507 0.169847 0.704554 0.043 Uiso 1 1 calc R U . . .
H8C H -0.164875 0.061731 0.781831 0.043 Uiso 1 1 calc R U . . .
Au1A Au 0.24306(2) 0.67522(2) 0.50943(2) 0.01526(2) Uani 1 1 d . . . . .
Cl1A Cl 0.12758(3) 0.66630(8) 0.55824(3) 0.02030(9) Uani 1 1 d . . . . .
O1A O 0.43082(11) 0.6068(3) 0.25709(9) 0.0267(4) Uani 1 1 d . . . . .
O2A O 0.54380(10) 0.6215(3) 0.33069(9) 0.0239(3) Uani 1 1 d . . . . .
N1A N 0.41268(10) 0.7251(2) 0.50328(10) 0.0148(3) Uani 1 1 d . . . . .
N2A N 0.35580(10) 0.6350(2) 0.39646(10) 0.0157(3) Uani 1 1 d . . . . .
C1A C 0.34298(12) 0.6794(3) 0.46730(11) 0.0146(3) Uani 1 1 d . . . . .
C2A C 0.46869(12) 0.7087(3) 0.45615(12) 0.0162(4) Uani 1 1 d . . . . .
H2A H 0.521904 0.733011 0.468326 0.019 Uiso 1 1 calc R U . . .
C3A C 0.43364(12) 0.6509(3) 0.38863(12) 0.0170(4) Uani 1 1 d . . . . .
C4A C 0.42480(13) 0.8014(3) 0.57911(12) 0.0193(4) Uani 1 1 d . . . . .
H4AA H 0.413940 0.937564 0.577845 0.029 Uiso 1 1 calc R U . . .
H4AB H 0.478210 0.780280 0.599854 0.029 Uiso 1 1 calc R U . . .
H4AC H 0.390418 0.737752 0.610643 0.029 Uiso 1 1 calc R U . . .
C5A C 0.29613(13) 0.5728(3) 0.33888(12) 0.0210(4) Uani 1 1 d . . . . .
H5AA H 0.309774 0.448628 0.319872 0.032 Uiso 1 1 calc R U . . .
H5AB H 0.291201 0.664501 0.297637 0.032 Uiso 1 1 calc R U . . .
H5AC H 0.247214 0.563345 0.360343 0.032 Uiso 1 1 calc R U . . .
C6A C 0.46705(13) 0.6239(3) 0.31799(13) 0.0193(4) Uani 1 1 d . . . . .
C7A C 0.58543(15) 0.6156(4) 0.26471(14) 0.0293(5) Uani 1 1 d . . . . .
H7AA H 0.590598 0.745005 0.244667 0.035 Uiso 1 1 calc R U . . .
H7AB H 0.557166 0.537026 0.225133 0.035 Uiso 1 1 calc R U . . .
C8A C 0.66322(14) 0.5325(4) 0.28727(15) 0.0271(5) Uani 1 1 d . . . . .
H8AA H 0.687057 0.596975 0.332297 0.041 Uiso 1 1 calc R U . . .
H8AB H 0.695412 0.548911 0.246397 0.041 Uiso 1 1 calc R U . . .
H8AC H 0.658052 0.397250 0.297849 0.041 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'
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'
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'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
9 -2 -24 0.0323
11 -9 -7 0.0466
-20 0 16 0.0418
-16 -4 17 0.0341
18 -6 -10 0.0409
20 0 -16 0.0371
24 0 -10 0.0437
-14 -2 -19 0.0401
0 0 -1 0.0233
0 0 1 0.0196
2 -6 20 0.0243
-3 10 6 0.0429
-1 4 -23 0.0365
2 0 1 0.0353
1 -1 1 0.0328
-1 -2 0 0.0468
-11 -2 23 0.0205
-24 -3 3 0.0375
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 178.42(6) . . ?
C6 O2 C7 115.91(17) . . ?
C1 N1 C2 111.04(17) . . ?
C1 N1 C4 124.31(17) . . ?
C2 N1 C4 124.57(18) . . ?
C1 N2 C3 109.81(17) . . ?
C1 N2 C5 124.58(18) . . ?
C3 N2 C5 125.32(17) . . ?
N1 C1 N2 105.84(17) . . ?
N1 C1 Au1 126.52(15) . . ?
N2 C1 Au1 127.58(15) . . ?
C3 C2 N1 106.89(18) . . ?
C2 C3 N2 106.40(17) . . ?
C2 C3 C6 128.94(19) . . ?
N2 C3 C6 124.59(19) . . ?
O1 C6 O2 124.5(2) . . ?
O1 C6 C3 125.8(2) . . ?
O2 C6 C3 109.73(18) . . ?
O2 C7 C8 107.35(19) . . ?
C1A Au1A Cl1A 179.28(6) . . ?
C6A O2A C7A 116.44(19) . . ?
C1A N1A C2A 110.82(17) . . ?
C1A N1A C4A 124.30(17) . . ?
C2A N1A C4A 124.54(18) . . ?
C1A N2A C3A 110.02(18) . . ?
C1A N2A C5A 123.84(18) . . ?
C3A N2A C5A 126.10(18) . . ?
N2A C1A N1A 105.57(17) . . ?
N2A C1A Au1A 126.88(16) . . ?
N1A C1A Au1A 127.54(15) . . ?
C3A C2A N1A 106.93(19) . . ?
C2A C3A N2A 106.65(18) . . ?
C2A C3A C6A 128.7(2) . . ?
N2A C3A C6A 124.5(2) . . ?
O1A C6A O2A 124.8(2) . . ?
O1A C6A C3A 125.1(2) . . ?
O2A C6A C3A 110.1(2) . . ?
O2A C7A C8A 108.3(2) . . ?
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 1.984(2) . ?
Au1 Cl1 2.2873(5) . ?
O1 C6 1.205(3) . ?
O2 C6 1.341(3) . ?
O2 C7 1.453(3) . ?
N1 C1 1.347(3) . ?
N1 C2 1.366(3) . ?
N1 C4 1.460(3) . ?
N2 C1 1.355(3) . ?
N2 C3 1.392(3) . ?
N2 C5 1.459(3) . ?
C2 C3 1.365(3) . ?
C3 C6 1.464(3) . ?
C7 C8 1.509(3) . ?
Au1A C1A 1.982(2) . ?
Au1A Cl1A 2.2930(5) . ?
O1A C6A 1.208(3) . ?
O2A C6A 1.340(3) . ?
O2A C7A 1.458(3) . ?
N1A C1A 1.356(3) . ?
N1A C2A 1.369(3) . ?
N1A C4A 1.457(3) . ?
N2A C1A 1.352(3) . ?
N2A C3A 1.391(3) . ?
N2A C5A 1.455(3) . ?
C2A C3A 1.359(3) . ?
C3A C6A 1.466(3) . ?
C7A C8A 1.499(4) . ?
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
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2 N1 C1 N2 -0.4(2) . . . . ?
C4 N1 C1 N2 176.63(18) . . . . ?
C2 N1 C1 Au1 177.15(15) . . . . ?
C4 N1 C1 Au1 -5.8(3) . . . . ?
C3 N2 C1 N1 0.9(2) . . . . ?
C5 N2 C1 N1 174.99(19) . . . . ?
C3 N2 C1 Au1 -176.61(15) . . . . ?
C5 N2 C1 Au1 -2.5(3) . . . . ?
C1 N1 C2 C3 -0.3(2) . . . . ?
C4 N1 C2 C3 -177.27(19) . . . . ?
N1 C2 C3 N2 0.8(2) . . . . ?
N1 C2 C3 C6 177.8(2) . . . . ?
C1 N2 C3 C2 -1.1(2) . . . . ?
C5 N2 C3 C2 -175.11(19) . . . . ?
C1 N2 C3 C6 -178.27(19) . . . . ?
C5 N2 C3 C6 7.7(3) . . . . ?
C7 O2 C6 O1 4.0(3) . . . . ?
C7 O2 C6 C3 -175.54(17) . . . . ?
C2 C3 C6 O1 -168.9(2) . . . . ?
N2 C3 C6 O1 7.6(3) . . . . ?
C2 C3 C6 O2 10.6(3) . . . . ?
N2 C3 C6 O2 -172.81(18) . . . . ?
C6 O2 C7 C8 -171.91(19) . . . . ?
C3A N2A C1A N1A 0.7(2) . . . . ?
C5A N2A C1A N1A 178.46(18) . . . . ?
C3A N2A C1A Au1A -178.68(14) . . . . ?
C5A N2A C1A Au1A -0.9(3) . . . . ?
C2A N1A C1A N2A -0.4(2) . . . . ?
C4A N1A C1A N2A 173.27(18) . . . . ?
C2A N1A C1A Au1A 178.97(15) . . . . ?
C4A N1A C1A Au1A -7.4(3) . . . . ?
C1A N1A C2A C3A -0.1(2) . . . . ?
C4A N1A C2A C3A -173.69(19) . . . . ?
N1A C2A C3A N2A 0.5(2) . . . . ?
N1A C2A C3A C6A 175.8(2) . . . . ?
C1A N2A C3A C2A -0.7(2) . . . . ?
C5A N2A C3A C2A -178.45(19) . . . . ?
C1A N2A C3A C6A -176.27(19) . . . . ?
C5A N2A C3A C6A 6.0(3) . . . . ?
C7A O2A C6A O1A 6.0(3) . . . . ?
C7A O2A C6A C3A -173.75(19) . . . . ?
C2A C3A C6A O1A -165.3(2) . . . . ?
N2A C3A C6A O1A 9.2(4) . . . . ?
C2A C3A C6A O2A 14.4(3) . . . . ?
N2A C3A C6A O2A -171.06(19) . . . . ?
C6A O2A C7A C8A -156.2(2) . . . . ?
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
8.6385 -1.9674 -23.9987 0.3826 -0.9239 0.0090
10.7742 -8.6994 -6.6517 0.3531 -0.4119 0.8401
-20.4939 0.4753 16.2993 -0.8526 0.5226 -0.0089
-16.3359 -4.3997 17.0841 -0.7408 0.4548 0.4944
18.2821 -5.9554 -9.8038 0.6897 -0.4219 0.5885
20.4939 -0.4753 -16.2993 0.8526 -0.5226 0.0089
23.6699 0.3672 -9.8094 0.9723 -0.2335 0.0089
-13.7488 -1.6557 -18.9151 -0.5197 -0.8480 -0.1037
-0.0002 -0.0008 -0.9999 0.0024 -0.0385 -0.0096
0.0002 0.0008 0.9999 -0.0024 0.0385 0.0096
1.6074 -6.0686 19.6874 -0.0492 0.6157 0.7865
-3.0739 9.5770 6.4882 -0.0361 0.4714 -0.8812
-0.9860 4.2088 -22.6537 0.0614 -0.7728 -0.6317
1.9980 0.0004 0.9987 0.0773 0.0499 0.0214
0.9961 -0.9991 1.0031 0.0266 0.0194 0.1121
-1.0049 -1.9993 0.0083 -0.0615 -0.0553 0.1874
-11.2264 -2.1383 23.0013 -0.5273 0.7682 0.3631
-23.8344 -2.6108 3.2139 -0.9867 -0.0774 0.1432
