# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_sm27db
_audit_block_doi                 10.5517/ccdc.csd.cc2hkdxd
_database_code_depnum_ccdc_archive 'CCDC 2310644'
loop_
_audit_author_name
_audit_author_address
'Dirk Bockfeld'
;TU Braunschweig
Germany
;
_audit_update_record             
;
2023-12-27 deposited with the CCDC.	2024-01-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H14 Au K N4 O4, 4(H2 O)'
_chemical_formula_sum            'C12 H22 Au K N4 O8'
_chemical_formula_weight         586.40

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'
K K 0.2009 0.2494 '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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   3.78331(13)
_cell_length_b                   11.0885(5)
_cell_length_c                   11.4646(7)
_cell_angle_alpha                79.885(5)
_cell_angle_beta                 82.696(4)
_cell_angle_gamma                80.471(3)
_cell_volume                     464.56(4)
_cell_formula_units_Z            1
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    16710
_cell_measurement_theta_min      2.3890
_cell_measurement_theta_max      32.6680

_exptl_crystal_description       irregular
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.096
_exptl_crystal_F_000             284
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    8.188
_shelx_estimated_absorpt_T_min   0.394
_shelx_estimated_absorpt_T_max   0.853
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 1 -15 0.0256
0 -15 1 0.0097
5 4 2 0.0574
0 0 -16 0.0129
-5 -4 -3 0.0818
0 15 -1 0.0097
-1 -1 16 0.0116
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
1.3368 0.9885 -14.7506 -0.0090 0.0005 1.0000
0.1891 -15.0365 0.5861 0.9793 0.0767 -0.1874
5.3113 3.8611 1.6462 0.0754 -0.9541 0.2899
-0.2720 -0.3447 -15.9483 -0.0225 0.3018 0.9531
-5.3135 -3.8719 -2.6406 -0.0766 0.9703 -0.2294
-0.1891 15.0365 -0.5861 -0.9793 -0.0767 0.1874
-0.5282 -0.5256 15.5027 0.0294 -0.1527 -0.9878
_exptl_absorpt_correction_T_min  0.414
_exptl_absorpt_correction_T_max  1.000
_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.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.814
_oxdiff_exptl_absorpt_empirical_full_max 1.340
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_diffrn_ambient_temperature      100(2)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at offset/far, HyPix'
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_type            HyPix
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_number            4572
_diffrn_reflns_av_unetI/netI     0.0197
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.401
_diffrn_reflns_theta_max         32.576
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.869
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.869
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.869
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4572
_reflns_number_gt                4439
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;

_computing_structure_solution    
'SHELXT 2018/2 (G. M. Sheldrick, Acta Cryst., 2015, A71, 3-8)'
_computing_structure_refinement  
'SHELXL-2018/3 (G. M. Sheldrick, Acta Cryst., 2015, C71, 3-8)'
_computing_molecular_graphics    ?
_computing_publication_material  
'OLEX2 v1.3 (O. V. Dolomanov et al., J. Appl. Cryst., 2009, 42, 339-341)'

_refine_special_details          
;
 All H atoms were placed in idealised positions and refined using a riding
 model, with a common U restrained to be 1.2 (1.5 for methyl groups) times
 the equivalent isotropic displacement parameter of the parent atom.
 Ordered methyl groups were treated as rigid bodies and allowed to
 rotate around the E-CH3 bond.

 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.

 Some water molecules as well as the potassium atom were found disordered.

 Refined as a 2-component twin. Component 2 rotated by 179.6494°
 around [0.85 0.42 0.32] (reciprocal) or [1.00 0.00 -0.00] (direct).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+7.0826P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4572
_refine_ls_number_parameters     163
_refine_ls_number_restraints     24
_refine_ls_R_factor_all          0.0430
_refine_ls_R_factor_gt           0.0411
_refine_ls_wR_factor_ref         0.1022
_refine_ls_wR_factor_gt          0.1013
_refine_ls_goodness_of_fit_ref   1.155
_refine_ls_restrained_S_all      1.157
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 1.000000 0.000000 0.500000 0.01929(10) Uani 1 2 d S . P . .
K1 K 0.000000 0.500000 0.000000 0.033(3) Uani 0.51(5) 2 d S U P A 1
K1A K -0.026(5) 0.553(3) 0.0082(14) 0.041(4) Uani 0.25(2) 1 d . U P A -2
O1 O 0.4834(15) 0.4357(5) 0.1595(5) 0.0327(12) Uani 1 1 d . . . . .
O2 O 0.1893(15) 0.5539(5) 0.2914(5) 0.0319(12) Uani 1 1 d . . . . .
O3 O 0.016(9) 0.7020(18) 0.0816(15) 0.050(6) Uani 0.51(5) 1 d . . P A 1
H3A H -0.207690 0.702276 0.114741 0.075 Uiso 0.51(5) 1 d R U P A 1
H3B H 0.146640 0.642186 0.128740 0.075 Uiso 0.51(5) 1 d R U P A 1
O3A O 0.221(11) 0.726(2) 0.095(2) 0.065(9) Uani 0.49(5) 1 d G . P A -2
H3AA H 0.468499 0.716322 0.093709 0.097 Uiso 0.49(5) 1 d G U P A -2
H3AB H 0.190103 0.669774 0.166017 0.097 Uiso 0.49(5) 1 d G U P A -2
N1 N 0.6973(15) 0.2434(5) 0.3540(6) 0.0214(12) Uani 1 1 d . . . . .
N2 N 0.5253(14) 0.2410(5) 0.5403(6) 0.0202(11) Uani 1 1 d . . . . .
C1 C 0.7259(17) 0.1723(6) 0.4621(6) 0.0175(12) Uani 1 1 d . U . . .
C2 C 0.4800(18) 0.3562(6) 0.3647(7) 0.0222(13) Uani 1 1 d . . . . .
C3 C 0.3747(18) 0.3533(6) 0.4822(7) 0.0222(13) Uani 1 1 d . . . . .
H3 H 0.224248 0.417113 0.518039 0.027 Uiso 1 1 calc R U . . .
C4 C 0.8848(19) 0.2033(7) 0.2426(7) 0.0269(15) Uani 1 1 d . . . . .
H4A H 1.029135 0.121770 0.261412 0.040 Uiso 1 1 calc R U . . .
H4B H 1.042743 0.263366 0.203441 0.040 Uiso 1 1 calc R U . . .
H4C H 0.706518 0.198354 0.189307 0.040 Uiso 1 1 calc R U . . .
C5 C 0.461(2) 0.1989(7) 0.6670(7) 0.0275(15) Uani 1 1 d . . . . .
H5A H 0.202591 0.199107 0.689281 0.041 Uiso 1 1 calc R U . . .
H5B H 0.549659 0.254293 0.710815 0.041 Uiso 1 1 calc R U . . .
H5C H 0.589023 0.114631 0.686652 0.041 Uiso 1 1 calc R U . . .
C6 C 0.379(2) 0.4566(6) 0.2630(6) 0.0238(13) Uani 1 1 d . . . . .
O4 O 0.436(9) 1.025(3) 0.056(3) 0.093(14) Uani 0.37(3) 1 d G . P B -4
H4D H 0.628788 0.980407 0.082876 0.139 Uiso 0.37(3) 1 d G U P B -4
H4E H 0.246239 0.996161 0.094209 0.139 Uiso 0.37(3) 1 d G U P B -4
O4A O 0.580(8) 0.849(3) 0.002(2) 0.144(12) Uani 0.63(3) 1 d G U P B 3
H4AA H 0.757653 0.873304 0.028258 0.216 Uiso 0.63(3) 1 d G U P B 3
H4AB H 0.390038 0.876051 0.046193 0.216 Uiso 0.63(3) 1 d G U P B 3


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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 2.021(7) . ?
Au1 C1 2.021(7) 2_756 ?
K1 O3 2.59(2) 2_565 ?
K1 O3 2.59(2) . ?
K1 O1 2.601(6) 2_665 ?
K1 O1 2.601(6) 1_455 ?
K1 O1 2.675(6) 2_565 ?
K1 O1 2.675(6) . ?
K1 C6 3.426(7) 2_565 ?
K1 K1 3.78331(13) 1_455 ?
K1 K1 3.78331(13) 1_655 ?
K1A O3A 2.65(3) . ?
K1A O1 2.767(19) . ?
O1 C6 1.252(9) . ?
O2 C6 1.261(9) . ?
N1 C1 1.353(9) . ?
N1 C2 1.394(9) . ?
N1 C4 1.482(10) . ?
N2 C1 1.355(9) . ?
N2 C3 1.374(8) . ?
N2 C5 1.448(9) . ?
C2 C3 1.352(10) . ?
C2 C6 1.504(10) . ?

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 C1 180.0(2) . 2_756 ?
O3 K1 O3 180.0 2_565 . ?
O3 K1 O1 93.0(7) 2_565 2_665 ?
O3 K1 O1 87.0(7) . 2_665 ?
O3 K1 O1 87.0(7) 2_565 1_455 ?
O3 K1 O1 93.0(7) . 1_455 ?
O1 K1 O1 180.0 2_665 1_455 ?
O3 K1 O1 75.5(5) 2_565 2_565 ?
O3 K1 O1 104.5(5) . 2_565 ?
O1 K1 O1 91.60(18) 2_665 2_565 ?
O1 K1 O1 88.40(18) 1_455 2_565 ?
O3 K1 O1 104.5(5) 2_565 . ?
O3 K1 O1 75.5(5) . . ?
O1 K1 O1 88.40(18) 2_665 . ?
O1 K1 O1 91.60(18) 1_455 . ?
O1 K1 O1 180.00(16) 2_565 . ?
O3 K1 C6 65.6(4) 2_565 2_565 ?
O3 K1 C6 114.4(4) . 2_565 ?
O1 K1 C6 76.40(18) 2_665 2_565 ?
O1 K1 C6 103.60(18) 1_455 2_565 ?
O1 K1 C6 19.04(18) 2_565 2_565 ?
O1 K1 C6 160.96(18) . 2_565 ?
O3 K1 K1 77.7(7) 2_565 1_455 ?
O3 K1 K1 102.3(7) . 1_455 ?
O1 K1 K1 135.02(12) 2_665 1_455 ?
O1 K1 K1 44.98(12) 1_455 1_455 ?
O1 K1 K1 43.42(12) 2_565 1_455 ?
O1 K1 K1 136.58(12) . 1_455 ?
C6 K1 K1 59.55(13) 2_565 1_455 ?
O3 K1 K1 102.3(7) 2_565 1_655 ?
O3 K1 K1 77.7(7) . 1_655 ?
O1 K1 K1 44.98(12) 2_665 1_655 ?
O1 K1 K1 135.02(12) 1_455 1_655 ?
O1 K1 K1 136.58(12) 2_565 1_655 ?
O1 K1 K1 43.42(12) . 1_655 ?
C6 K1 K1 120.45(13) 2_565 1_655 ?
K1 K1 K1 180.0 1_455 1_655 ?
O3A K1A O1 72.1(6) . . ?
C6 O1 K1 134.7(5) . 1_655 ?
C6 O1 K1 116.7(5) . . ?
K1 O1 K1 91.60(18) 1_655 . ?
C6 O1 K1A 109.4(6) . . ?
C1 N1 C2 110.7(6) . . ?
C1 N1 C4 122.6(6) . . ?
C2 N1 C4 126.6(6) . . ?
C1 N2 C3 110.8(6) . . ?
C1 N2 C5 124.5(6) . . ?
C3 N2 C5 124.6(6) . . ?
N1 C1 N2 105.0(6) . . ?
N1 C1 Au1 127.9(5) . . ?
N2 C1 Au1 127.0(5) . . ?
C3 C2 N1 106.1(6) . . ?
C3 C2 C6 128.4(7) . . ?
N1 C2 C6 125.6(7) . . ?
C2 C3 N2 107.4(6) . . ?
O1 C6 O2 126.4(7) . . ?
O1 C6 C2 117.7(6) . . ?
O2 C6 C2 115.9(7) . . ?

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 0.1(7) . . . . ?
C4 N1 C1 N2 178.7(6) . . . . ?
C2 N1 C1 Au1 179.2(4) . . . . ?
C4 N1 C1 Au1 -2.2(9) . . . . ?
C3 N2 C1 N1 -0.2(7) . . . . ?
C5 N2 C1 N1 176.5(6) . . . . ?
C3 N2 C1 Au1 -179.3(4) . . . . ?
C5 N2 C1 Au1 -2.6(9) . . . . ?
C1 N1 C2 C3 0.0(7) . . . . ?
C4 N1 C2 C3 -178.5(6) . . . . ?
C1 N1 C2 C6 -178.0(6) . . . . ?
C4 N1 C2 C6 3.5(10) . . . . ?
N1 C2 C3 N2 -0.1(7) . . . . ?
C6 C2 C3 N2 177.8(6) . . . . ?
C1 N2 C3 C2 0.2(7) . . . . ?
C5 N2 C3 C2 -176.4(6) . . . . ?
K1 O1 C6 O2 79.3(10) 1_655 . . . ?
K1 O1 C6 O2 -43.5(9) . . . . ?
K1A O1 C6 O2 -32.3(11) . . . . ?
K1 O1 C6 C2 -101.9(7) 1_655 . . . ?
K1 O1 C6 C2 135.2(5) . . . . ?
K1A O1 C6 C2 146.5(7) . . . . ?
C3 C2 C6 O1 -174.1(7) . . . . ?
N1 C2 C6 O1 3.5(10) . . . . ?
C3 C2 C6 O2 4.8(11) . . . . ?
N1 C2 C6 O2 -177.6(6) . . . . ?

_refine_diff_density_max         2.007
_refine_diff_density_min         -2.056
_refine_diff_density_rms         0.254

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_sm14db
_audit_block_doi                 10.5517/ccdc.csd.cc2hkdt9
_database_code_depnum_ccdc_archive 'CCDC 2310641'
loop_
_audit_author_name
_audit_author_address
'Dirk Bockfeld'
;TU Braunschweig
Germany
;
_audit_update_record             
;
2023-12-27 deposited with the CCDC.	2024-01-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H16 Au N4 O4, Cl, H2 O'
_chemical_formula_sum            'C12 H18 Au Cl N4 O5'
_chemical_formula_weight         530.72

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 -4.4197 7.2980 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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.
;

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'

_cell_length_a                   3.6946(5)
_cell_length_b                   20.679(2)
_cell_length_c                   10.7340(11)
_cell_angle_alpha                90
_cell_angle_beta                 99.603(11)
_cell_angle_gamma                90
_cell_volume                     808.59(16)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6019
_cell_measurement_theta_min      4.2740
_cell_measurement_theta_max      75.4220

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.180
_exptl_crystal_F_000             508
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.043
_exptl_crystal_size_mid          0.014
_exptl_crystal_size_min          0.011
_exptl_absorpt_coefficient_mu    18.908
_shelx_estimated_absorpt_T_min   0.497
_shelx_estimated_absorpt_T_max   0.819
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -12 3 0.0013
0 12 -3 0.0105
2 -5 3 0.0054
0 9 5 0.0021
-2 7 -2 0.0070
0 -7 -6 0.0123
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
0.0873 -12.3635 2.6214 0.2033 -0.6840 0.7006
-0.0873 12.3635 -2.6214 -0.2033 0.6840 -0.7006
1.8011 -5.3374 2.7517 -0.5004 -0.1488 0.8529
-0.1819 8.8453 5.2285 -0.8537 -0.2531 -0.4551
-1.8280 6.5426 -2.0465 0.3853 0.1147 -0.9156
-0.2503 -7.1827 -5.6357 0.9322 0.2765 0.2335
_exptl_absorpt_correction_T_min  0.59375
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.101a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.370
_oxdiff_exptl_absorpt_empirical_full_max 2.901
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
- B-factor correction
;
_diffrn_ambient_temperature      100(2)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at home/near, HyPix'
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_type            HyPix
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_number            20080
_diffrn_reflns_av_unetI/netI     0.0353
_diffrn_reflns_av_R_equivalents  0.0905
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         4.276
_diffrn_reflns_theta_max         77.572
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             1721
_reflns_number_gt                1316
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlisPro 1.171.42.101a (Rigaku OD, 2023)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.101a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.101a (Rigaku OD, 2023)'

_computing_structure_solution    
'SHELXS-2013/1 (G. M. Sheldrick, Acta Cryst., 2008, A64, 112-122)'
_computing_structure_refinement  
'SHELXL-2018/3 (G. M. Sheldrick, Acta Cryst., 2015, C71, 3-8)'
_computing_molecular_graphics    ?
_computing_publication_material  
'OLEX2 v1.3 (O. V. Dolomanov et al., J. Appl. Cryst., 2009, 42, 339-341)'

_refine_special_details          
;
 All H atoms were placed in idealised positions and refined using a riding
 model, with a common U restrained to be 1.2 (1.5 for methyl groups) times
 the equivalent isotropic displacement parameter of the parent atom.
 Ordered methyl groups were treated as rigid bodies and allowed to 
 rotate around the E-CH3 bond.

 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.

 In the first runs (and during the pre-experiment) a second component with
 different cell parameters (doubled a axis) and a different orientation was
 present. The corresponding reflections are missing in the following runs.
 Possibly a small fragment of the (multi)crystal was blown away by the N2
 stream or phase transition took place during the during the first part of
 the experiment. For data reduction the first runs and some sunburst frames
 were skipped.
 
 The Cl atom was refined with a disorder model with one cl atom and a molecule 
 of water with occupancies of 50 % each. Unfortunately, this model needs
 rather strong restraints to the Cl and O atoms (EADP). 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+7.9885P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     patterson
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1721
_refine_ls_number_parameters     115
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0735
_refine_ls_R_factor_gt           0.0553
_refine_ls_wR_factor_ref         0.1013
_refine_ls_wR_factor_gt          0.0962
_refine_ls_goodness_of_fit_ref   1.246
_refine_ls_restrained_S_all      1.246
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.500000 0.500000 0.500000 0.04114(18) Uani 1 2 d S . P . .
O2 O 0.366(2) 0.2147(3) 0.4163(7) 0.0491(19) Uani 1 1 d . . . . .
O1 O 0.700(2) 0.1903(4) 0.6040(6) 0.0442(17) Uani 1 1 d . . . . .
H1 H 0.698540 0.153212 0.572114 0.066 Uiso 1 1 calc R U . . .
N1 N 0.482(3) 0.3529(4) 0.4859(7) 0.0357(16) Uani 1 1 d . . . . .
N2 N 0.778(2) 0.3852(4) 0.6657(6) 0.0355(18) Uani 1 1 d . . . . .
C1 C 0.586(2) 0.4073(5) 0.5529(8) 0.037(2) Uani 1 1 d . . . . .
C2 C 0.602(2) 0.2976(5) 0.5575(7) 0.035(2) Uani 1 1 d . . . . .
C3 C 0.790(2) 0.3199(5) 0.6692(8) 0.035(2) Uani 1 1 d . . . . .
H3 H 0.908269 0.294191 0.737383 0.042 Uiso 1 1 calc R U . . .
C4 C 0.264(3) 0.3531(6) 0.3589(8) 0.044(2) Uani 1 1 d . . . . .
H4A H 0.162631 0.396373 0.339335 0.066 Uiso 1 1 calc R U . . .
H4B H 0.063032 0.321820 0.354991 0.066 Uiso 1 1 calc R U . . .
H4C H 0.420608 0.341119 0.297297 0.066 Uiso 1 1 calc R U . . .
C5 C 0.535(3) 0.2312(5) 0.5190(7) 0.036(2) Uani 1 1 d . . . . .
C6 C 0.954(3) 0.4287(6) 0.7681(8) 0.048(3) Uani 1 1 d . . . . .
H6A H 1.066538 0.465399 0.731235 0.072 Uiso 1 1 calc R U . . .
H6B H 1.142413 0.404901 0.824928 0.072 Uiso 1 1 calc R U . . .
H6C H 0.767423 0.444706 0.815717 0.072 Uiso 1 1 calc R U . . .
Cl1 Cl 0.549(6) 0.0557(7) 0.5854(16) 0.065(3) Uani 0.5 1 d . . P A -2
O3 O 0.624(17) 0.064(2) 0.578(5) 0.065(3) Uani 0.5 1 d G . P B -1
H3A H 0.858764 0.068764 0.579397 0.097 Uiso 0.5 1 d G U P B -1
H3B H 0.568267 0.029013 0.533270 0.097 Uiso 0.5 1 d G U P B -1


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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 2.010(10) 3_666 ?
Au1 C1 2.010(10) . ?
O2 C5 1.221(10) . ?
O1 C5 1.316(10) . ?
N1 C1 1.356(12) . ?
N1 C2 1.407(12) . ?
N1 C4 1.463(10) . ?
N2 C3 1.351(12) . ?
N2 C1 1.375(11) . ?
N2 C6 1.483(11) . ?
C2 C3 1.363(11) . ?
C2 C5 1.443(13) . ?

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 C1 180.0 3_666 . ?
C1 N1 C2 110.4(7) . . ?
C1 N1 C4 123.8(8) . . ?
C2 N1 C4 125.8(8) . . ?
C3 N2 C1 111.5(8) . . ?
C3 N2 C6 125.3(8) . . ?
C1 N2 C6 123.2(9) . . ?
N1 C1 N2 104.5(8) . . ?
N1 C1 Au1 128.6(6) . . ?
N2 C1 Au1 126.8(7) . . ?
C3 C2 N1 105.9(8) . . ?
C3 C2 C5 127.7(8) . . ?
N1 C2 C5 126.4(7) . . ?
N2 C3 C2 107.7(8) . . ?
O2 C5 O1 123.7(9) . . ?
O2 C5 C2 124.1(8) . . ?
O1 C5 C2 112.1(7) . . ?

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 1.1(10) . . . . ?
C4 N1 C1 N2 179.1(10) . . . . ?
C2 N1 C1 Au1 179.2(7) . . . . ?
C4 N1 C1 Au1 -2.7(15) . . . . ?
C3 N2 C1 N1 -0.5(11) . . . . ?
C6 N2 C1 N1 178.4(9) . . . . ?
C3 N2 C1 Au1 -178.7(6) . . . . ?
C6 N2 C1 Au1 0.2(13) . . . . ?
C1 N1 C2 C3 -1.3(11) . . . . ?
C4 N1 C2 C3 -179.3(10) . . . . ?
C1 N1 C2 C5 178.5(9) . . . . ?
C4 N1 C2 C5 0.5(16) . . . . ?
C1 N2 C3 C2 -0.3(11) . . . . ?
C6 N2 C3 C2 -179.2(8) . . . . ?
N1 C2 C3 N2 1.0(10) . . . . ?
C5 C2 C3 N2 -178.8(9) . . . . ?
C3 C2 C5 O2 -179.4(10) . . . . ?
N1 C2 C5 O2 0.9(18) . . . . ?
C3 C2 C5 O1 -3.7(15) . . . . ?
N1 C2 C5 O1 176.6(9) . . . . ?

_refine_diff_density_max         1.628
_refine_diff_density_min         -0.968
_refine_diff_density_rms         0.139

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_sm13db
_audit_block_doi                 10.5517/ccdc.csd.cc2hkdyf
_database_code_depnum_ccdc_archive 'CCDC 2310645'
loop_
_audit_author_name
_audit_author_address
'Dirk Bockfeld'
;TU Braunschweig
Germany
;
_audit_update_record             
;
2023-11-27 deposited with the CCDC.	2024-01-15 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT971_sm13db              
;
PROBLEM: Check Calcd Resid. Dens.
RESPONSE: Cu K\a radiation was necessary to observe at least weak diffraction
 spots leading to strong absorption effects compared to f. e. Mo K\a radiation.
;
_vrf_PLAT972_sm13db              
;
PROBLEM: Check Calcd Resid. Dens.
RESPONSE: Cu K\a radiation was necessary to observe at least weak diffraction
 spots leading to strong absorption effects compared to f. e. Mo K\a radiation.
;
_vrf_PLAT973_sm13db              
;
PROBLEM: Check Calcd Positive Resid. Density on
RESPONSE: Cu K\a radiation was necessary to observe at least weak diffraction
 spots leading to strong absorption effects compared to f. e. Mo K\a radiation.
;
_vrf_PLAT097_sm13db              
;
PROBLEM: Large Reported Max.  (Positive) Residual Density
RESPONSE: Cu K\a radiation was necessary to observe at least weak diffraction
 spots leading to strong absorption effects compared to f. e. Mo K\a radiation.
;
_vrf_PLAT342_sm13db              
;
PROBLEM: Low Bond Precision on  C-C Bonds
RESPONSE: The crystal structure suffers from poor resolution. Despite several
 attempts only very small crystals were obtained from this compound.
 Accordingly, this structure is verifying the connectivity of the given
 compound but not suitable for deriving any metric parameters.
;
_vrf_PLAT420_sm13db              
;
PROBLEM: D-H Without Acceptor
RESPONSE:  Because of the low resolution, H atoms which are possibly involved in
 hydrogen bonding were not refined freely. Solvent H atom positions are not
 reliable.
;
# end Validation Reply Form

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H14 Au K N4 O4, 2(H2 O), C H4 O'
_chemical_formula_sum            'C13 H22 Au K N4 O7'
_chemical_formula_weight         582.41

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 -4.4197 7.2980 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
K K 0.3868 1.0657 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   3.8030(2)
_cell_length_b                   10.9370(12)
_cell_length_c                   11.4861(8)
_cell_angle_alpha                79.722(7)
_cell_angle_beta                 82.574(5)
_cell_angle_gamma                81.366(7)
_cell_volume                     462.17(7)
_cell_formula_units_Z            1
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    1869
_cell_measurement_theta_min      4.1470
_cell_measurement_theta_max      69.5760

_exptl_crystal_description       irregular
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.093
_exptl_crystal_F_000             282
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.059
_exptl_crystal_size_mid          0.024
_exptl_crystal_size_min          0.013
_exptl_absorpt_coefficient_mu    17.375
_shelx_estimated_absorpt_T_min   0.427
_shelx_estimated_absorpt_T_max   0.806
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 3 -6 0.0056
0 -3 6 0.0059
2 -1 5 0.0198
-2 -1 -3 0.0191
0 4 7 0.0137
0 -3 -7 0.0033
0 7 0 0.0100
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
-0.0428 3.1671 -5.9719 -0.0278 0.1529 0.9879
-0.3402 -3.4118 5.6886 0.0556 -0.3025 -0.9515
1.8190 -0.8385 5.0666 -0.1127 0.6043 -0.7888
-2.3959 -1.0363 -2.6925 0.1692 -0.9095 0.3796
-0.0400 3.9635 6.6720 0.8613 0.1599 -0.4823
-0.0076 -3.4362 -6.9527 -0.8130 -0.1508 0.5624
-0.4640 6.6533 0.2172 0.8231 0.1531 0.5469
_exptl_absorpt_correction_T_min  0.554
_exptl_absorpt_correction_T_max  0.874
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.81a (Rigaku Oxford Diffraction, 2020)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.506
_oxdiff_exptl_absorpt_empirical_full_max 1.731
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_diffrn_ambient_temperature      100(2)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at home/near, HyPix'
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_type            HyPix
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_number            5680
_diffrn_reflns_av_unetI/netI     0.0755
_diffrn_reflns_av_R_equivalents  0.0884
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         4.143
_diffrn_reflns_theta_max         76.221
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.924
_diffrn_measured_fraction_theta_full 0.975
_diffrn_reflns_Laue_measured_fraction_max 0.924
_diffrn_reflns_Laue_measured_fraction_full 0.975
_diffrn_reflns_point_group_measured_fraction_max 0.924
_diffrn_reflns_point_group_measured_fraction_full 0.975
_reflns_number_total             1792
_reflns_number_gt                1634
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlisPro 1.171.40.81a (Rigaku OD, 2020)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.81a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.81a (Rigaku OD, 2020)'

_computing_structure_solution    
'SHELXT 2018/2 (G. M. Sheldrick, Acta Cryst., 2015, A71, 3-8)'
_computing_structure_refinement  
'SHELXL-2018/3 (G. M. Sheldrick, Acta Cryst., 2015, C71, 3-8)'
_computing_molecular_graphics    ?
_computing_publication_material  
'OLEX2 v1.2 (O. V. Dolomanov et al., J. Appl. Cryst., 2009, 42, 339-341)'

_refine_special_details          
;
 Because of the low resolution, H atoms which are possibly involved in
 hydrogen bonding were not refined freely. Solvent H atom positions are
 not reliable.
 
 All H atoms were placed in idealised positions and refined using a riding
 model, with a common U restrained to be 1.2 (1.5 for methyl groups) times
 the equivalent isotropic displacement parameter of the parent atom.
 Ordered methyl groups were treated as rigid bodies and allowed to
 rotate around the E-CH3 bond.

 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.

 The crystal structure suffers from poor resolution. Despite several attempts
 only very small crystals were obtained from this compound. Additionally, Cu Kα
 radiation was necessary to observe at least weak diffraction spots leading to
 strong absorption effects compared to f. e. Mo Kα radiation. Accordingly, this
 structure is verifying the connectivity of the given compound but not suitable
 for deriving any metric parameters.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1792
_refine_ls_number_parameters     146
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1125
_refine_ls_R_factor_gt           0.1068
_refine_ls_wR_factor_ref         0.2801
_refine_ls_wR_factor_gt          0.2720
_refine_ls_goodness_of_fit_ref   1.209
_refine_ls_restrained_S_all      1.209
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 1.000000 0.000000 0.500000 0.0391(5) Uani 1 2 d S . P . .
K1 K 0.000000 0.500000 0.000000 0.068(2) Uani 1 2 d S . P . .
O1 O 0.173(5) 0.5529(15) 0.2950(13) 0.050(4) Uani 1 1 d . . . . .
O2 O 0.471(4) 0.4370(14) 0.1628(12) 0.044(3) Uani 1 1 d . . . . .
N1 N 0.688(4) 0.2444(14) 0.3543(15) 0.035(3) Uani 1 1 d . . . . .
N2 N 0.531(4) 0.2393(14) 0.5403(15) 0.037(3) Uani 1 1 d . . . . .
C1 C 0.716(5) 0.1726(14) 0.4591(19) 0.037(4) Uani 1 1 d . . . . .
C2 C 0.469(5) 0.355(2) 0.3657(17) 0.040(4) Uani 1 1 d . . . . .
C3 C 0.366(4) 0.3538(18) 0.4849(17) 0.036(4) Uani 1 1 d . . . . .
H3 H 0.215313 0.416752 0.521548 0.044 Uiso 1 1 calc R U . . .
C4 C 0.862(7) 0.203(2) 0.245(2) 0.052(5) Uani 1 1 d . . . . .
H4A H 1.055063 0.252819 0.211353 0.078 Uiso 1 1 calc R U . . .
H4B H 0.686777 0.212505 0.187318 0.078 Uiso 1 1 calc R U . . .
H4C H 0.962180 0.114049 0.262258 0.078 Uiso 1 1 calc R U . . .
C5 C 0.479(5) 0.199(2) 0.671(2) 0.049(5) Uani 1 1 d . . . . .
H5A H 0.363078 0.123087 0.689455 0.074 Uiso 1 1 calc R U . . .
H5B H 0.328254 0.266135 0.708092 0.074 Uiso 1 1 calc R U . . .
H5C H 0.711885 0.182746 0.703201 0.074 Uiso 1 1 calc R U . . .
C6 C 0.364(5) 0.4569(19) 0.2639(19) 0.042(4) Uani 1 1 d . . . . .
O3A O -0.048(17) 0.709(4) 0.087(3) 0.054(16) Uani 0.46(11) 1 d . . P A 1
H3AA H -0.239542 0.717323 0.145841 0.081 Uiso 0.46(11) 1 d R U P A 1
H3AB H 0.146338 0.709213 0.128101 0.081 Uiso 0.46(11) 1 d R U P A 1
O3B O 0.181(19) 0.723(3) 0.092(3) 0.068(19) Uani 0.54(11) 1 d . . P A 2
H3BA H 0.417405 0.725453 0.080529 0.102 Uiso 0.54(11) 1 d R U P A 2
H3BB H 0.134065 0.713149 0.171802 0.102 Uiso 0.54(11) 1 d R U P A 2
O99 O 0.424(14) 0.157(4) -0.006(4) 0.081(12) Uani 0.5 1 d . . P B -1
H99 H 0.291208 0.188162 0.048965 0.122 Uiso 0.5 1 calc R U P B -1
C99 C 0.450(16) 0.027(5) 0.019(8) 0.074(18) Uani 0.5 1 d . . P B -1
H99A H 0.445854 -0.006233 -0.054215 0.111 Uiso 0.5 1 calc R U P B -1
H99B H 0.246969 0.002448 0.076192 0.111 Uiso 0.5 1 calc R U P B -1
H99C H 0.673660 -0.007092 0.053797 0.111 Uiso 0.5 1 calc R U P B -1


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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 2.037(15) . ?
Au1 C1 2.037(15) 2_756 ?
K1 O3A 2.62(4) . ?
K1 O3A 2.62(4) 2_565 ?
K1 O2 2.646(14) 2_665 ?
K1 O2 2.646(14) 1_455 ?
K1 O2 2.687(15) 2_565 ?
K1 O2 2.687(15) . ?
K1 O3B 3.03(6) 2_565 ?
K1 O3B 3.03(6) . ?
K1 C6 3.42(2) . ?
K1 C6 3.42(2) 2_565 ?
K1 K1 3.8030(2) 1_455 ?
K1 K1 3.8030(2) 1_655 ?
O1 C6 1.26(3) . ?
O2 C6 1.23(3) . ?
N1 C1 1.32(3) . ?
N1 C2 1.38(3) . ?
N1 C4 1.46(3) . ?
N2 C1 1.35(3) . ?
N2 C3 1.40(2) . ?
N2 C5 1.49(3) . ?
C2 C3 1.37(3) . ?
C2 C6 1.51(3) . ?
O99 C99 1.39(8) . ?

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 C1 180.0 . 2_756 ?
O3A K1 O3A 180.0 . 2_565 ?
O3A K1 O2 92.7(13) . 2_665 ?
O3A K1 O2 87.3(13) 2_565 2_665 ?
O3A K1 O2 87.3(13) . 1_455 ?
O3A K1 O2 92.7(13) 2_565 1_455 ?
O2 K1 O2 180.0 2_665 1_455 ?
O3A K1 O2 101.7(11) . 2_565 ?
O3A K1 O2 78.3(11) 2_565 2_565 ?
O2 K1 O2 91.0(4) 2_665 2_565 ?
O2 K1 O2 89.0(4) 1_455 2_565 ?
O3A K1 O2 78.3(11) . . ?
O3A K1 O2 101.7(11) 2_565 . ?
O2 K1 O2 89.0(4) 2_665 . ?
O2 K1 O2 91.0(4) 1_455 . ?
O2 K1 O2 180.0 2_565 . ?
O3A K1 O3B 163.1(10) . 2_565 ?
O3A K1 O3B 16.9(10) 2_565 2_565 ?
O2 K1 O3B 99.4(10) 2_665 2_565 ?
O2 K1 O3B 80.6(10) 1_455 2_565 ?
O2 K1 O3B 66.7(10) 2_565 2_565 ?
O2 K1 O3B 113.3(10) . 2_565 ?
O2 K1 O3B 80.6(10) 2_665 . ?
O2 K1 O3B 99.4(10) 1_455 . ?
O2 K1 O3B 113.3(10) 2_565 . ?
O2 K1 O3B 66.7(10) . . ?
O3B K1 O3B 180(2) 2_565 . ?
O3A K1 C6 67.4(10) . . ?
O3A K1 C6 112.6(10) 2_565 . ?
O2 K1 C6 104.2(5) 2_665 . ?
O2 K1 C6 75.8(5) 1_455 . ?
O2 K1 C6 161.4(4) 2_565 . ?
O2 K1 C6 18.6(4) . . ?
O3B K1 C6 119.9(9) 2_565 . ?
O3B K1 C6 60.1(9) . . ?
O3A K1 C6 112.6(10) . 2_565 ?
O3A K1 C6 67.4(10) 2_565 2_565 ?
O2 K1 C6 75.8(4) 2_665 2_565 ?
O2 K1 C6 104.2(5) 1_455 2_565 ?
O2 K1 C6 18.6(4) 2_565 2_565 ?
O2 K1 C6 161.4(4) . 2_565 ?
C6 K1 C6 180.0 . 2_565 ?
O3A K1 K1 96.3(14) . 1_455 ?
O3A K1 K1 83.7(14) 2_565 1_455 ?
O2 K1 K1 135.1(3) 2_665 1_455 ?
O2 K1 K1 44.9(3) 1_455 1_455 ?
O2 K1 K1 44.1(3) 2_565 1_455 ?
O2 K1 K1 135.9(3) . 1_455 ?
C6 K1 K1 119.9(3) . 1_455 ?
C6 K1 K1 60.1(3) 2_565 1_455 ?
O3A K1 K1 83.7(14) . 1_655 ?
O3A K1 K1 96.3(14) 2_565 1_655 ?
O2 K1 K1 44.9(3) 2_665 1_655 ?
O2 K1 K1 135.1(3) 1_455 1_655 ?
O2 K1 K1 135.9(3) 2_565 1_655 ?
O2 K1 K1 44.1(3) . 1_655 ?
C6 K1 K1 60.1(3) . 1_655 ?
C6 K1 K1 119.9(3) 2_565 1_655 ?
K1 K1 K1 180.0 1_455 1_655 ?
C6 O2 K1 136.3(14) . 1_655 ?
C6 O2 K1 117.0(12) . . ?
K1 O2 K1 91.0(4) 1_655 . ?
C1 N1 C2 110.8(16) . . ?
C1 N1 C4 121.4(17) . . ?
C2 N1 C4 127.7(17) . . ?
C1 N2 C3 110.8(16) . . ?
C1 N2 C5 127.2(16) . . ?
C3 N2 C5 121.9(16) . . ?
N1 C1 N2 106.3(14) . . ?
N1 C1 Au1 129.3(15) . . ?
N2 C1 Au1 124.3(14) . . ?
C3 C2 N1 107.2(17) . . ?
C3 C2 C6 127.5(18) . . ?
N1 C2 C6 125.3(17) . . ?
C2 C3 N2 104.8(16) . . ?
O2 C6 O1 128.1(19) . . ?
O2 C6 C2 117.2(17) . . ?
O1 C6 C2 114.7(18) . . ?
O2 C6 K1 44.4(10) . . ?
O1 C6 K1 92.2(13) . . ?
C2 C6 K1 141.1(14) . . ?

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 -4(2) . . . . ?
C4 N1 C1 N2 179.0(18) . . . . ?
C2 N1 C1 Au1 -179.8(14) . . . . ?
C4 N1 C1 Au1 3(3) . . . . ?
C3 N2 C1 N1 3(2) . . . . ?
C5 N2 C1 N1 179.5(17) . . . . ?
C3 N2 C1 Au1 179.9(12) . . . . ?
C5 N2 C1 Au1 -4(3) . . . . ?
C1 N1 C2 C3 2(2) . . . . ?
C4 N1 C2 C3 179.7(19) . . . . ?
C1 N1 C2 C6 -177.3(18) . . . . ?
C4 N1 C2 C6 0(3) . . . . ?
N1 C2 C3 N2 0(2) . . . . ?
C6 C2 C3 N2 179.4(19) . . . . ?
C1 N2 C3 C2 -2(2) . . . . ?
C5 N2 C3 C2 -178.3(17) . . . . ?
K1 O2 C6 O1 81(3) 1_655 . . . ?
K1 O2 C6 O1 -43(3) . . . . ?
K1 O2 C6 C2 -99(2) 1_655 . . . ?
K1 O2 C6 C2 136.5(15) . . . . ?
K1 O2 C6 K1 124(2) 1_655 . . . ?
C3 C2 C6 O2 -176.3(19) . . . . ?
N1 C2 C6 O2 3(3) . . . . ?
C3 C2 C6 O1 3(3) . . . . ?
N1 C2 C6 O1 -177.1(19) . . . . ?
C3 C2 C6 K1 -126(2) . . . . ?
N1 C2 C6 K1 53(3) . . . . ?

_refine_diff_density_max         8.532
_refine_diff_density_min         -5.490
_refine_diff_density_rms         0.596

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_sm01db2
_audit_block_doi                 10.5517/ccdc.csd.cc2hkdr7
_database_code_depnum_ccdc_archive 'CCDC 2310639'
loop_
_audit_author_name
_audit_author_address
'Dirk Bockfeld'
;TU Braunschweig
Germany
;
_audit_update_record             
;
2023-11-27 deposited with the CCDC.	2024-01-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H8 N2 O2, 2(H2 O)'
_chemical_formula_sum            'C6 H12 N2 O4'
_chemical_formula_weight         176.18

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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.
;

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'

_cell_length_a                   4.81570(10)
_cell_length_b                   17.5289(3)
_cell_length_c                   10.0642(2)
_cell_angle_alpha                90
_cell_angle_beta                 98.656(2)
_cell_angle_gamma                90
_cell_volume                     839.88(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    17858
_cell_measurement_theta_min      5.0930
_cell_measurement_theta_max      77.0640

_exptl_crystal_description       irregular
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.393
_exptl_crystal_F_000             376
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.183
_exptl_crystal_size_mid          0.087
_exptl_crystal_size_min          0.033
_exptl_absorpt_coefficient_mu    1.005
_shelx_estimated_absorpt_T_min   0.838
_shelx_estimated_absorpt_T_max   0.968
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -11 -1 0.0095
0 11 1 0.0187
2 -3 5 0.0211
2 -4 -4 0.0684
0 1 -6 0.0697
-2 3 -5 0.0720
-1 2 6 0.0093
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
0.1592 -11.2814 -0.8279 0.8758 0.0696 0.4776
-0.3670 11.2065 0.9411 -0.8418 -0.0670 -0.5355
1.6999 -3.4437 4.5202 0.0685 -0.8691 0.4898
2.4143 -3.8252 -4.2413 -0.0321 0.3993 0.9163
-0.1406 0.8858 -6.3873 -0.0787 0.9934 0.0839
-1.6500 3.3660 -4.6226 -0.0694 0.8796 -0.4706
-1.3560 1.7710 6.1579 0.0639 -0.8029 -0.5927
_exptl_absorpt_correction_T_min  0.47044
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.45a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.596
_oxdiff_exptl_absorpt_empirical_full_max 1.760
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_diffrn_ambient_temperature      100(2)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at home/near, HyPix'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            HyPix
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measurement_method       'ω scan'
_diffrn_reflns_number            3755
_diffrn_reflns_av_unetI/netI     0.0036
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         5.112
_diffrn_reflns_theta_max         77.909
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3755
_reflns_number_gt                3322
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;

_computing_data_collection       'CrysAlisPro 1.171.40.45a (Rigaku OD, 2019)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.45a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.45a (Rigaku OD, 2019)'
_computing_structure_solution    
'SHELXT 2018/2 (G. M. Sheldrick, Acta Cryst., 2015, A71, 3-8)'
_computing_structure_refinement  
'SHELXL-2018/3 (G. M. Sheldrick, Acta Cryst., 2015, C71, 3-8)'
_computing_molecular_graphics    ?
_computing_publication_material  
'OLEX2 v1.2 (O. V. Dolomanov et al., J. Appl. Cryst., 2009, 42, 339-341)'

_refine_special_details          
;
The hydrogen atoms of the water molecules were refined freely. All other
H atoms were placed in idealised positions and refined using a riding
model, with a common U restrained to be 1.2 (1.5 for methyl groups) times
the equivalent isotropic displacement parameter of the parent atom.
Ordered methyl groups were treated as rigid bodies and allowed to
rotate around the E-CH3 bond.

Refinement of F² against ALL reflections.  The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement.  R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.

Refined as a 2-component twin. Component 2 rotated by 175.7235°
around [-0.00 1.00 0.01] (reciprocal) or [-0.05 1.00 0.02] (direct)
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0870P)²+0.0851P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3755
_refine_ls_number_parameters     128
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0474
_refine_ls_R_factor_gt           0.0448
_refine_ls_wR_factor_ref         0.1475
_refine_ls_wR_factor_gt          0.1439
_refine_ls_goodness_of_fit_ref   1.143
_refine_ls_restrained_S_all      1.143
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
O1 O 0.3431(2) 0.66128(5) 0.75206(10) 0.0263(3) Uani 1 1 d . . . . .
O2 O 0.2489(2) 0.78288(5) 0.79684(10) 0.0233(3) Uani 1 1 d . . . . .
O3 O 0.3581(2) 0.50463(6) 0.74566(12) 0.0323(3) Uani 1 1 d . . . . .
H3A H 0.185(6) 0.4864(13) 0.720(2) 0.050(6) Uiso 1 1 d . . . . .
H3B H 0.343(5) 0.5562(13) 0.738(2) 0.040(5) Uiso 1 1 d . . . . .
N1 N 0.7132(2) 0.71498(6) 0.56781(11) 0.0197(3) Uani 1 1 d . . . . .
N2 N 0.8022(2) 0.83292(6) 0.52579(11) 0.0200(3) Uani 1 1 d . . . . .
C1 C 0.8575(3) 0.76059(7) 0.49749(12) 0.0199(3) Uani 1 1 d . . . . .
H1 H 0.979590 0.744367 0.437170 0.024 Uiso 1 1 calc R U . . .
C2 C 0.5585(3) 0.75973(7) 0.64422(12) 0.0181(3) Uani 1 1 d . . . . .
C3 C 0.6168(3) 0.83373(7) 0.61685(13) 0.0196(3) Uani 1 1 d . . . . .
H3 H 0.542712 0.877741 0.654001 0.023 Uiso 1 1 calc R U . . .
C4 C 0.7242(3) 0.63158(7) 0.55963(14) 0.0243(3) Uani 1 1 d . . . . .
H4A H 0.796460 0.610637 0.648395 0.037 Uiso 1 1 calc R U . . .
H4B H 0.848517 0.616711 0.495407 0.037 Uiso 1 1 calc R U . . .
H4C H 0.535081 0.611629 0.529603 0.037 Uiso 1 1 calc R U . . .
C5 C 0.3677(3) 0.73171(7) 0.73871(12) 0.0187(3) Uani 1 1 d . . . . .
C6 C 0.9199(3) 0.90022(8) 0.46879(14) 0.0252(3) Uani 1 1 d . . . . .
H6A H 0.767558 0.930636 0.419317 0.038 Uiso 1 1 calc R U . . .
H6B H 1.048647 0.884079 0.407481 0.038 Uiso 1 1 calc R U . . .
H6C H 1.022334 0.931031 0.541391 0.038 Uiso 1 1 calc R U . . .
H4D H 0.317(6) 0.9599(14) 0.806(3) 0.061(7) Uiso 1 1 d . . . . .
O4 O 0.1584(2) 0.93666(6) 0.81563(12) 0.0314(3) Uani 1 1 d . . . . .
H4E H 0.192(5) 0.8883(15) 0.803(2) 0.046(6) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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
O1 C5 1.2493(16) . ?
O2 C5 1.2550(15) . ?
N1 C1 1.3309(17) . ?
N1 C2 1.3905(15) . ?
N1 C4 1.4656(17) . ?
N2 C1 1.3352(16) . ?
N2 C3 1.3723(18) . ?
N2 C6 1.4628(17) . ?
C2 C3 1.3640(17) . ?
C2 C5 1.5011(17) . ?

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 N1 C2 108.74(11) . . ?
C1 N1 C4 122.89(11) . . ?
C2 N1 C4 128.37(11) . . ?
C1 N2 C3 108.84(11) . . ?
C1 N2 C6 125.50(11) . . ?
C3 N2 C6 125.66(11) . . ?
N1 C1 N2 108.67(11) . . ?
C3 C2 N1 106.33(11) . . ?
C3 C2 C5 127.11(12) . . ?
N1 C2 C5 126.56(11) . . ?
C2 C3 N2 107.42(11) . . ?
O1 C5 O2 126.78(12) . . ?
O1 C5 C2 117.94(12) . . ?
O2 C5 C2 115.28(10) . . ?

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 0.10(14) . . . . ?
C4 N1 C1 N2 179.55(11) . . . . ?
C3 N2 C1 N1 -0.04(15) . . . . ?
C6 N2 C1 N1 -179.97(11) . . . . ?
C1 N1 C2 C3 -0.11(14) . . . . ?
C4 N1 C2 C3 -179.53(12) . . . . ?
C1 N1 C2 C5 -179.65(12) . . . . ?
C4 N1 C2 C5 0.93(19) . . . . ?
N1 C2 C3 N2 0.09(14) . . . . ?
C5 C2 C3 N2 179.62(11) . . . . ?
C1 N2 C3 C2 -0.03(15) . . . . ?
C6 N2 C3 C2 179.90(11) . . . . ?
C3 C2 C5 O1 -179.10(12) . . . . ?
N1 C2 C5 O1 0.34(18) . . . . ?
C3 C2 C5 O2 0.73(19) . . . . ?
N1 C2 C5 O2 -179.82(11) . . . . ?

_refine_diff_density_max         0.333
_refine_diff_density_min         -0.312
_refine_diff_density_rms         0.060

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_sm09db
_audit_block_doi                 10.5517/ccdc.csd.cc2hkdvb
_database_code_depnum_ccdc_archive 'CCDC 2310642'
loop_
_audit_author_name
_audit_author_address
'Dirk Bockfeld'
;TU Braunschweig
Germany
;
_audit_update_record             
;
2023-11-27 deposited with the CCDC.	2024-01-15 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT971_sm09db              
;
PROBLEM: Check Calcd Resid. Dens. ...
RESPONSE: The residual electron density is caused by absorption effects. An
 increase in residual electron density is observed for diffraction data from
 higher theta angles. Cutting the resolution to e.g. 0.8 \%A results in a
 residual density maximum of about 0.8 e\%A^-3^.
;
_vrf_PLAT972_sm09db              
;
PROBLEM: Check Calcd Resid. Dens. ...
RESPONSE: The residual electron density is caused by absorption effects. An
 increase in residual electron density is observed for diffraction data from
 higher theta angles. Cutting the resolution to e.g. 0.8 \%A results in a
 residual density maximum of about 0.8 e\%A^-3^.
;
# end Validation Reply Form

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H8 Au Cl N2 O2'

_chemical_formula_sum            'C6 H8 Au Cl N2 O2'
_chemical_formula_weight         372.56

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   6.76910(10)
_cell_length_b                   12.2956(2)
_cell_length_c                   11.0786(2)
_cell_angle_alpha                90
_cell_angle_beta                 102.935(2)
_cell_angle_gamma                90
_cell_volume                     898.68(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    63220
_cell_measurement_theta_min      3.2100
_cell_measurement_theta_max      58.7470

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.754
_exptl_crystal_F_000             680
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.264
_exptl_crystal_size_mid          0.119
_exptl_crystal_size_min          0.099
_exptl_absorpt_coefficient_mu    16.627
_shelx_estimated_absorpt_T_min   0.097
_shelx_estimated_absorpt_T_max   0.290
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 17 4 0.0595
1 15 7 0.0571
6 -9 -11 0.0996
0 -15 -8 0.0496
-7 7 11 0.0996
7 5 -11 0.1124
0 5 -15 0.0586
-9 -7 6 0.1093
0 -5 15 0.0610
0 10 -13 0.0533
1 -9 12 0.0598
-4 12 -8 0.0808
7 -11 1 0.0981
7 -12 -3 0.0972
-6 14 2 0.0947
6 13 -1 0.0919
6 12 3 0.0878
1 12 11 0.0533
-1 11 12 0.0541
0 -12 -11 0.0448
8 -2 4 0.1052
0 -10 13 0.0587
-6 5 -8 0.1033
0 13 -10 0.0566
3 13 -10 0.0766
-3 -13 10 0.0726
0 16 -6 0.0603
0 -16 6 0.0603
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
-1.1723 16.8000 3.6997 0.7428 0.6341 0.2150
0.6436 15.4018 6.6810 0.4975 0.8111 0.3077
6.1554 -8.7961 -10.9487 -0.4510 -0.7367 0.5039
0.3242 -15.0941 -7.5918 -0.5119 -0.8349 -0.2021
-6.9717 6.9562 10.9591 0.4105 0.6708 -0.6177
7.3414 5.3666 -11.1989 0.1464 -0.3512 0.9248
0.4650 5.1306 -14.6943 0.6088 -0.7125 0.3489
-8.6292 -6.6011 6.0992 0.0051 -0.0075 -1.0000
-0.1895 -4.9704 14.6518 -0.6155 0.7202 -0.3201
0.0322 9.6738 -12.6480 0.7878 -0.4825 0.3828
0.6847 -9.4012 12.4957 -0.8106 0.4965 -0.3105
-3.9315 11.7471 -7.8338 0.9723 -0.2335 0.0090
6.9169 -11.1545 1.1997 -0.9302 -0.0728 0.3597
6.6472 -12.4180 -2.9801 -0.8610 -0.3562 0.3630
-5.9038 13.6149 2.3791 0.8917 0.3690 -0.2621
6.4866 12.6236 -1.0090 0.2544 0.4168 0.8727
6.1892 11.9838 2.5864 0.1441 0.6033 0.7844
0.8721 12.0913 10.5013 0.2284 0.9518 0.2049
-0.8346 11.0301 11.9742 0.2335 0.9723 0.0090
0.1007 -11.5419 -11.3947 -0.2324 -0.9681 -0.0938
8.2684 -1.6085 4.4277 -0.6498 0.3975 0.6479
-0.3398 -9.7615 12.6973 -0.7763 0.4763 -0.4130
-6.1762 5.1129 -8.4334 0.8049 -0.4930 -0.3302
-0.4623 13.3157 -9.5570 0.9003 -0.2166 0.3775
3.3291 12.9022 -9.9000 0.6815 -0.1644 0.7132
-3.0063 -13.0274 9.9360 -0.7060 0.1702 -0.6874
0.0346 15.9366 -6.0174 0.8987 0.0702 0.4329
-0.0346 -15.9366 6.0174 -0.8987 -0.0702 -0.4329
_exptl_absorpt_correction_T_min  0.055
_exptl_absorpt_correction_T_max  0.638
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.81a (Rigaku Oxford Diffraction, 2020)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.632
_oxdiff_exptl_absorpt_empirical_full_max 1.627
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_diffrn_ambient_temperature      100(2)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at offset/far, HyPix'
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_type            HyPix
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_number            127069
_diffrn_reflns_av_unetI/netI     0.0252
_diffrn_reflns_av_R_equivalents  0.0576
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         3.238
_diffrn_reflns_theta_max         58.805
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             13013
_reflns_number_gt                10944
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlisPro 1.171.40.81a (Rigaku OD, 2020)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.81a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.81a (Rigaku OD, 2020)'

_computing_structure_solution    
'SHELXT 2018/2 (G. M. Sheldrick, Acta Cryst., 2015, A71, 3-8)'
_computing_structure_refinement  
'SHELXL-2018/3 (G. M. Sheldrick, Acta Cryst., 2015, C71, 3-8)'
_computing_molecular_graphics    ?
_computing_publication_material  
'OLEX2 v1.2 (O. V. Dolomanov et al., J. Appl. Cryst., 2009, 42, 339-341)'

_refine_special_details          
;
 All H atoms were placed in idealised positions and refined using a riding
 model, with a common U restrained to be 1.2 (1.5 for methyl groups) times
 the equivalent isotropic displacement parameter of the parent atom.
 Ordered methyl groups were treated as rigid bodies and allowed to
 rotate around the E-CH3 bond.

 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0202P)²+0.7823P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         13013
_refine_ls_number_parameters     112
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0335
_refine_ls_R_factor_gt           0.0254
_refine_ls_wR_factor_ref         0.0596
_refine_ls_wR_factor_gt          0.0576
_refine_ls_goodness_of_fit_ref   1.113
_refine_ls_restrained_S_all      1.113
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000

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 0.69162(2) 0.56373(2) 0.58329(2) 0.01283(1) Uani 1 1 d . . . . .
Cl1 Cl 0.84411(6) 0.64912(3) 0.44437(3) 0.01852(5) Uani 1 1 d . . . . .
O1 O 0.0929(2) 0.55849(10) 0.89506(13) 0.02046(18) Uani 1 1 d . . . . .
O2 O 0.2032(2) 0.40173(11) 0.99269(12) 0.02106(19) Uani 1 1 d . . . . .
H2 H 0.116592 0.416811 1.033816 0.032 Uiso 1 1 calc R U . . .
N1 N 0.41138(17) 0.53565(9) 0.75596(10) 0.01323(13) Uani 1 1 d . . . . .
N2 N 0.62292(19) 0.40165(10) 0.77267(11) 0.01533(15) Uani 1 1 d . . . . .
C1 C 0.56651(19) 0.49672(10) 0.71115(11) 0.01346(15) Uani 1 1 d . . . . .
C2 C 0.3695(2) 0.46512(11) 0.84480(11) 0.01409(15) Uani 1 1 d . . . . .
C3 C 0.5035(2) 0.38071(11) 0.85445(13) 0.01588(17) Uani 1 1 d . . . . .
H3 H 0.512066 0.319444 0.907613 0.019 Uiso 1 1 calc R U . . .
C4 C 0.2090(2) 0.48063(11) 0.91213(12) 0.01541(17) Uani 1 1 d . . . . .
C5 C 0.2954(2) 0.63288(12) 0.70817(14) 0.01755(19) Uani 1 1 d . . . . .
H5A H 0.355665 0.667012 0.644971 0.026 Uiso 1 1 calc R U . . .
H5B H 0.298071 0.684301 0.776098 0.026 Uiso 1 1 calc R U . . .
H5C H 0.154895 0.612462 0.671427 0.026 Uiso 1 1 calc R U . . .
C6 C 0.7763(3) 0.32776(14) 0.74639(19) 0.0239(3) Uani 1 1 d . . . . .
H6A H 0.869289 0.368004 0.706529 0.036 Uiso 1 1 calc R U . . .
H6B H 0.710402 0.269816 0.691022 0.036 Uiso 1 1 calc R U . . .
H6C H 0.852423 0.295758 0.823958 0.036 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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 1.9849(12) . ?
Au1 Cl1 2.2908(3) . ?
Au1 Au1 3.23241(11) 3_666 ?
O1 C4 1.2260(18) . ?
O2 C4 1.3247(18) . ?
O2 H2 0.8400 . ?
N1 C1 1.3460(16) . ?
N1 C2 1.3878(16) . ?
N1 C5 1.4626(18) . ?
N2 C1 1.3639(17) . ?
N2 C3 1.3666(17) . ?
N2 C6 1.4573(19) . ?
C2 C3 1.3670(19) . ?
C2 C4 1.4613(18) . ?
C3 H3 0.9500 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?

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 176.50(4) . . ?
C1 Au1 Au1 77.88(4) . 3_666 ?
Cl1 Au1 Au1 105.273(10) . 3_666 ?
C4 O2 H2 109.5 . . ?
C1 N1 C2 109.84(11) . . ?
C1 N1 C5 123.84(11) . . ?
C2 N1 C5 126.10(11) . . ?
C1 N2 C3 110.60(11) . . ?
C1 N2 C6 124.53(12) . . ?
C3 N2 C6 124.64(12) . . ?
N1 C1 N2 105.95(11) . . ?
N1 C1 Au1 127.47(9) . . ?
N2 C1 Au1 126.58(9) . . ?
C3 C2 N1 107.00(11) . . ?
C3 C2 C4 127.99(12) . . ?
N1 C2 C4 125.01(12) . . ?
N2 C3 C2 106.60(11) . . ?
N2 C3 H3 126.7 . . ?
C2 C3 H3 126.7 . . ?
O1 C4 O2 124.14(13) . . ?
O1 C4 C2 123.17(13) . . ?
O2 C4 C2 112.69(12) . . ?
N1 C5 H5A 109.5 . . ?
N1 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
N1 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
N2 C6 H6A 109.5 . . ?
N2 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
N2 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?

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 -0.33(15) . . . . ?
C5 N1 C1 N2 -175.25(12) . . . . ?
C2 N1 C1 Au1 -179.65(9) . . . . ?
C5 N1 C1 Au1 5.43(19) . . . . ?
C3 N2 C1 N1 0.48(15) . . . . ?
C6 N2 C1 N1 175.11(15) . . . . ?
C3 N2 C1 Au1 179.80(10) . . . . ?
C6 N2 C1 Au1 -5.6(2) . . . . ?
C1 N1 C2 C3 0.08(15) . . . . ?
C5 N1 C2 C3 174.85(13) . . . . ?
C1 N1 C2 C4 -179.24(12) . . . . ?
C5 N1 C2 C4 -4.5(2) . . . . ?
C1 N2 C3 C2 -0.43(16) . . . . ?
C6 N2 C3 C2 -175.06(15) . . . . ?
N1 C2 C3 N2 0.21(15) . . . . ?
C4 C2 C3 N2 179.50(13) . . . . ?
C3 C2 C4 O1 -178.42(15) . . . . ?
N1 C2 C4 O1 0.8(2) . . . . ?
C3 C2 C4 O2 1.5(2) . . . . ?
N1 C2 C4 O2 -179.34(13) . . . . ?

_refine_diff_density_max         4.381
_refine_diff_density_min         -3.580
_refine_diff_density_rms         0.217

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_sm07db
_audit_block_doi                 10.5517/ccdc.csd.cc2hkds8
_database_code_depnum_ccdc_archive 'CCDC 2310640'
loop_
_audit_author_name
_audit_author_address
'Dirk Bockfeld'
;TU Braunschweig
Germany
;
_audit_update_record             
;
2023-11-27 deposited with the CCDC.	2024-01-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H8 N2 O2, C H4 O'
_chemical_formula_sum            'C7 H12 N2 O3'
_chemical_formula_weight         172.19

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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.
;

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'

_cell_length_a                   4.43360(10)
_cell_length_b                   17.9129(2)
_cell_length_c                   10.4981(2)
_cell_angle_alpha                90
_cell_angle_beta                 95.263(2)
_cell_angle_gamma                90
_cell_volume                     830.23(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    10805
_cell_measurement_theta_min      4.2390
_cell_measurement_theta_max      76.7440

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.378
_exptl_crystal_F_000             368
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.707
_exptl_crystal_size_mid          0.304
_exptl_crystal_size_min          0.175
_exptl_absorpt_coefficient_mu    0.913
_shelx_estimated_absorpt_T_min   0.565
_shelx_estimated_absorpt_T_max   0.857
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 12 0 0.0617
-2 -4 -5 0.3600
0 -12 0 0.0975
2 0 5 0.2980
1 8 4 0.2093
2 1 -5 0.1491
2 4 4 0.2684
2 4 5 0.2864
-2 -4 -4 0.3428
-2 -1 4 0.1519
-1 -11 1 0.0998
2 8 3 0.2111
1 -3 5 0.3160
1 11 -1 0.0747
-1 2 -6 0.4140
1 -10 -2 0.1219
-1 10 2 0.0987
-2 0 -4 0.3712
2 -2 4 0.2925
-2 4 4 0.1397
-2 4 4 0.1354
2 -4 -4 0.1440
-1 -5 -5 0.3691
-2 -3 -4 0.3465
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
-0.1593 11.6079 0.1517 -0.8746 -0.3632 0.3212
-1.5948 -4.4162 -4.6803 0.0387 0.0171 -0.9991
0.2428 -11.5835 0.0827 0.8876 0.3686 -0.2762
1.7773 -0.2888 4.9479 0.3367 0.1387 0.9313
1.1424 8.3661 3.6199 -0.4070 -0.1698 0.8975
2.3151 0.7659 -4.5095 -0.3830 0.9231 0.0344
2.1035 4.0052 3.5414 -0.0886 0.2116 0.9733
1.5003 3.9253 4.9928 0.0206 -0.0516 0.9985
-2.0118 -4.0149 -3.8124 0.0703 -0.1674 -0.9834
-2.3326 -0.8107 4.4535 0.3828 -0.9227 -0.0458
-0.5273 -11.2852 1.1788 0.9457 0.0753 -0.3161
1.5037 7.7665 3.2709 -0.3881 -0.0316 0.9211
1.2910 -3.2004 5.4888 0.5999 0.0468 0.7987
0.6035 11.2918 -0.9079 -0.9288 -0.0740 0.3631
-1.3781 2.1709 -5.5209 -0.5227 -0.0407 -0.8516
1.1059 -10.4049 -1.7779 0.6646 0.7016 -0.2570
-1.1128 10.4002 1.7624 -0.6652 -0.7022 0.2537
-2.1332 0.4116 -4.0843 -0.2848 -0.2991 -0.9107
2.2026 -1.5268 3.7960 0.3499 0.3679 0.8615
-2.1641 4.2754 4.1817 -0.0253 -0.9936 0.1101
-2.2451 4.1165 3.9870 -0.0255 -0.9975 0.0661
2.2067 -4.1940 -4.0816 0.0254 0.9959 -0.0873
-1.1727 -4.5843 -5.3352 0.0036 0.1818 -0.9833
-2.0222 -3.1968 -4.0140 -0.0056 -0.1778 -0.9840
_exptl_absorpt_correction_T_min  0.207
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.61a (Rigaku Oxford Diffraction, 2019)
Numerical absorption correction based on gaussian integration over
            a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.804
_oxdiff_exptl_absorpt_empirical_full_max 1.418
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_diffrn_ambient_temperature      100(2)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at home/near, HyPix'
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_type            HyPix
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measurement_method       'ω scan'
_diffrn_reflns_number            17690
_diffrn_reflns_av_unetI/netI     0.0138
_diffrn_reflns_av_R_equivalents  0.0358
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         4.898
_diffrn_reflns_theta_max         77.597
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             1745
_reflns_number_gt                1687
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlisPro 1.171.40.61a (Rigaku OD, 2019)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.61a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.61a (Rigaku OD, 2019)'

_computing_structure_solution    
'SHELXT 2018/2 (G. M. Sheldrick, Acta Cryst., 2015, A71, 3-8)'
_computing_structure_refinement  
'SHELXL-2018/3 (G. M. Sheldrick, Acta Cryst., 2015, C71, 3-8)'
_computing_molecular_graphics    ?
_computing_publication_material  
'OLEX2 v1.2 (O. V. Dolomanov et al., J. Appl. Cryst., 2009, 42, 339-341)'

_refine_special_details          
;
 The hydrogen atom H3A of teh methanol molecule was refined freely.
 All H atoms were placed in idealised positions and refined using a riding
 model, with a common U restrained to be 1.2 (1.5 for methyl groups) times
 the equivalent isotropic displacement parameter of the parent atom.
 Ordered methyl groups were treated as rigid bodies and allowed to
 rotate around the E-CH3 bond.

 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.

;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0474P)²+0.2290P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1745
_refine_ls_number_parameters     116
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0330
_refine_ls_R_factor_gt           0.0321
_refine_ls_wR_factor_ref         0.0885
_refine_ls_wR_factor_gt          0.0878
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_restrained_S_all      1.067
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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
O1 O 0.91800(17) 0.18972(4) 0.28027(7) 0.0248(2) Uani 1 1 d . . . . .
O2 O 1.02347(17) 0.30920(4) 0.23840(7) 0.02327(19) Uani 1 1 d . . . . .
N1 N 0.55174(18) 0.23920(5) 0.47904(7) 0.0183(2) Uani 1 1 d . . . . .
N2 N 0.45064(17) 0.35318(5) 0.52782(7) 0.0181(2) Uani 1 1 d . . . . .
C1 C 0.4012(2) 0.28207(6) 0.55520(9) 0.0189(2) Uani 1 1 d . . . . .
H1 H 0.278596 0.264676 0.618648 0.023 Uiso 1 1 calc R U . . .
C2 C 0.7059(2) 0.28490(5) 0.39960(9) 0.0175(2) Uani 1 1 d . . . . .
C3 C 0.6400(2) 0.35620(5) 0.43134(9) 0.0179(2) Uani 1 1 d . . . . .
H3 H 0.711803 0.400217 0.393655 0.021 Uiso 1 1 calc R U . . .
C4 C 0.5445(2) 0.15753(6) 0.48410(10) 0.0241(2) Uani 1 1 d . . . . .
H4A H 0.445896 0.138086 0.403500 0.036 Uiso 1 1 calc R U . . .
H4B H 0.430735 0.141587 0.555102 0.036 Uiso 1 1 calc R U . . .
H4C H 0.751885 0.138265 0.497078 0.036 Uiso 1 1 calc R U . . .
C5 C 0.3273(2) 0.41706(6) 0.59272(9) 0.0226(2) Uani 1 1 d . . . . .
H5A H 0.493319 0.445076 0.638573 0.034 Uiso 1 1 calc R U . . .
H5B H 0.188735 0.399275 0.653671 0.034 Uiso 1 1 calc R U . . .
H5C H 0.217252 0.449599 0.529392 0.034 Uiso 1 1 calc R U . . .
C6 C 0.8986(2) 0.25815(6) 0.29785(9) 0.0183(2) Uani 1 1 d . . . . .
O3 O 1.12493(18) 0.45588(4) 0.28512(7) 0.0271(2) Uani 1 1 d . . . . .
C7 C 1.0314(3) 0.49197(6) 0.16874(10) 0.0275(3) Uani 1 1 d . . . . .
H7A H 1.140060 0.470686 0.100094 0.041 Uiso 1 1 calc R U . . .
H7B H 1.076105 0.545435 0.176657 0.041 Uiso 1 1 calc R U . . .
H7C H 0.813067 0.484862 0.148604 0.041 Uiso 1 1 calc R U . . .
H3A H 1.098(3) 0.4073(10) 0.2734(15) 0.041(4) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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
O1 C6 1.2437(12) . ?
O2 C6 1.2632(12) . ?
N1 C1 1.3314(13) . ?
N1 C2 1.3920(12) . ?
N1 C4 1.4643(13) . ?
N2 C1 1.3285(13) . ?
N2 C3 1.3746(12) . ?
N2 C5 1.4632(12) . ?
C1 H1 0.9500 . ?
C2 C3 1.3585(13) . ?
C2 C6 1.5059(13) . ?
C3 H3 0.9500 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
O3 C7 1.4106(13) . ?
O3 H3A 0.885(18) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?

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 N1 C2 108.74(8) . . ?
C1 N1 C4 122.72(8) . . ?
C2 N1 C4 128.54(8) . . ?
C1 N2 C3 108.75(8) . . ?
C1 N2 C5 124.95(8) . . ?
C3 N2 C5 126.29(8) . . ?
N2 C1 N1 108.74(9) . . ?
N2 C1 H1 125.6 . . ?
N1 C1 H1 125.6 . . ?
C3 C2 N1 106.11(8) . . ?
C3 C2 C6 128.46(9) . . ?
N1 C2 C6 125.41(9) . . ?
C2 C3 N2 107.65(8) . . ?
C2 C3 H3 126.2 . . ?
N2 C3 H3 126.2 . . ?
N1 C4 H4A 109.5 . . ?
N1 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
N1 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
N2 C5 H5A 109.5 . . ?
N2 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
N2 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
O1 C6 O2 126.92(9) . . ?
O1 C6 C2 118.06(9) . . ?
O2 C6 C2 115.02(9) . . ?
C7 O3 H3A 107.7(10) . . ?
O3 C7 H7A 109.5 . . ?
O3 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
O3 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?

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
C3 N2 C1 N1 -0.25(11) . . . . ?
C5 N2 C1 N1 -178.99(8) . . . . ?
C2 N1 C1 N2 0.29(10) . . . . ?
C4 N1 C1 N2 -179.72(8) . . . . ?
C1 N1 C2 C3 -0.21(10) . . . . ?
C4 N1 C2 C3 179.79(9) . . . . ?
C1 N1 C2 C6 -178.85(9) . . . . ?
C4 N1 C2 C6 1.16(15) . . . . ?
N1 C2 C3 N2 0.06(10) . . . . ?
C6 C2 C3 N2 178.65(9) . . . . ?
C1 N2 C3 C2 0.11(11) . . . . ?
C5 N2 C3 C2 178.83(9) . . . . ?
C3 C2 C6 O1 -176.57(9) . . . . ?
N1 C2 C6 O1 1.76(14) . . . . ?
C3 C2 C6 O2 3.08(15) . . . . ?
N1 C2 C6 O2 -178.59(8) . . . . ?

_refine_diff_density_max         0.247
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.040

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_sm18db
_audit_block_doi                 10.5517/ccdc.csd.cc2hkdwc
_database_code_depnum_ccdc_archive 'CCDC 2310643'
loop_
_audit_author_name
_audit_author_address
'Dirk Bockfeld'
;TU Braunschweig
Germany
;
_audit_update_record             
;
2023-11-27 deposited with the CCDC.	2024-01-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H15 Au N4 O4, 6(H2 O)'
_chemical_formula_sum            'C12 H27 Au N4 O10'
_chemical_formula_weight         584.34

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 -4.4197 7.2980 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   4.3054(4)
_cell_length_b                   20.233(3)
_cell_length_c                   11.3141(11)
_cell_angle_alpha                90
_cell_angle_beta                 91.190(9)
_cell_angle_gamma                90
_cell_volume                     985.4(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2380
_cell_measurement_theta_min      4.3750
_cell_measurement_theta_max      75.3950

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.969
_exptl_crystal_F_000             572
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.020
_exptl_crystal_size_min          0.010
_exptl_absorpt_coefficient_mu    14.559
_shelx_estimated_absorpt_T_min   0.204
_shelx_estimated_absorpt_T_max   0.868
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-3 -3 1 0.0145
3 0 -1 0.1362
0 13 -2 0.0076
0 -13 2 0.0035
0 0 7 0.0076
0 0 -7 0.0057
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
-2.6768 -3.0127 1.4463 0.1663 0.3479 0.9226
2.7714 -0.3708 -1.1113 -0.0567 -0.1176 -0.9914
0.3945 12.6933 -1.5684 -0.4301 -0.9027 -0.0090
-0.3945 -12.6933 1.5684 0.4301 0.9027 0.0090
0.2629 -0.1564 7.2970 -0.7936 0.6084 0.0093
-0.2629 0.1564 -7.2970 0.7936 -0.6084 -0.0093
_exptl_absorpt_correction_T_min  0.43715
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.112a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.544
_oxdiff_exptl_absorpt_empirical_full_max 3.079
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
- B-factor correction
;
_diffrn_ambient_temperature      100(2)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at home/near, HyPix'
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_type            HyPix
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_number            14935
_diffrn_reflns_av_unetI/netI     0.0460
_diffrn_reflns_av_R_equivalents  0.0664
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         4.370
_diffrn_reflns_theta_max         75.892
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.950
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.950
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.950
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             1958
_reflns_number_gt                1302
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlisPro 1.171.41.112a (Rigaku OD, 2021)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.112a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.112a (Rigaku OD, 2021)'

_computing_structure_solution    
'SHELXT 2018/2 (G. M. Sheldrick, Acta Cryst., 2015, A71, 3-8)'
_computing_structure_refinement  
'SHELXL-2018/3 (G. M. Sheldrick, Acta Cryst., 2015, C71, 3-8)'
_computing_molecular_graphics    ?
_computing_publication_material  
'OLEX2 v1.3 (O. V. Dolomanov et al., J. Appl. Cryst., 2009, 42, 339-341)'

_refine_special_details          
;
 All H atoms were placed in idealised positions and refined using a riding
 model, with a common U restrained to be 1.2 (1.5 for methyl groups) times
 the equivalent isotropic displacement parameter of the parent atom.
 Ordered methyl groups were treated as rigid bodies and allowed to
 rotate around the E-CH3 bond.

 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.

 The observed reflections were relatively broad. This was taken into account
 by overriding the peak integration mask sizes by factor 2.00.
 
 Because of the low data resolution H-atoms have not been refined freely.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0322P)²+10.2934P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1958
_refine_ls_number_parameters     136
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0705
_refine_ls_R_factor_gt           0.0432
_refine_ls_wR_factor_ref         0.1073
_refine_ls_wR_factor_gt          0.0975
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_restrained_S_all      1.074
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.500000 0.500000 0.000000 0.03114(17) Uani 1 2 d S . P . .
O1 O -0.3303(14) 0.4994(4) 0.4143(5) 0.0413(14) Uani 1 1 d . . . . .
H1 H -0.500000 0.500000 0.500000 0.11(7) Uiso 1 2 d S . P . .
O2 O -0.2277(17) 0.6048(4) 0.4660(6) 0.0461(17) Uani 1 1 d . . . . .
N1 N 0.1092(17) 0.5151(3) 0.2209(6) 0.0274(19) Uani 1 1 d . . . . .
N2 N 0.272(2) 0.6091(4) 0.1585(6) 0.0376(19) Uani 1 1 d . . . . .
C1 C 0.276(2) 0.5430(5) 0.1359(7) 0.0294(19) Uani 1 1 d . . . . .
C2 C 0.004(2) 0.5640(5) 0.2984(8) 0.033(2) Uani 1 1 d . . . . .
C3 C 0.108(3) 0.6225(6) 0.2553(8) 0.043(2) Uani 1 1 d . . . . .
H3 H 0.071795 0.665034 0.287693 0.052 Uiso 1 1 calc R U . . .
C4 C 0.064(2) 0.4444(5) 0.2327(8) 0.037(2) Uani 1 1 d . . . . .
H4A H 0.161557 0.421587 0.166805 0.056 Uiso 1 1 calc R U . . .
H4B H -0.159360 0.434599 0.231787 0.056 Uiso 1 1 calc R U . . .
H4C H 0.157717 0.429300 0.307539 0.056 Uiso 1 1 calc R U . . .
C5 C 0.423(3) 0.6594(6) 0.0853(9) 0.052(3) Uani 1 1 d . . . . .
H5A H 0.264225 0.685131 0.042419 0.079 Uiso 1 1 calc R U . . .
H5B H 0.558635 0.637676 0.028644 0.079 Uiso 1 1 calc R U . . .
H5C H 0.547155 0.688951 0.136163 0.079 Uiso 1 1 calc R U . . .
C6 C -0.199(2) 0.5553(5) 0.3999(8) 0.037(2) Uani 1 1 d . . . . .
O3 O 0.2850(19) 0.6747(4) 0.5431(6) 0.053(2) Uani 1 1 d G . . . .
H3A H 0.432968 0.649861 0.516481 0.079 Uiso 1 1 d G U . . .
H3B H 0.118427 0.661051 0.505772 0.079 Uiso 1 1 d G U . . .
O4 O 0.373(4) 0.7822(6) 0.3918(9) 0.109(4) Uani 1 1 d G . . . .
H4D H 0.204045 0.772996 0.351328 0.163 Uiso 1 1 d G U . . .
H4E H 0.372347 0.754452 0.450571 0.163 Uiso 1 1 d G U . . .
O5 O -0.127(4) 0.7820(6) 0.2679(10) 0.119(5) Uani 1 1 d G . . . .
H5D H -0.315913 0.788429 0.290741 0.178 Uiso 1 1 d G U . . .
H5E H -0.102588 0.811018 0.195002 0.178 Uiso 1 1 d G U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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 2.027(8) . ?
Au1 C1 2.027(8) 3_665 ?
O1 C6 1.277(12) . ?
O2 C6 1.257(12) . ?
N1 C1 1.337(11) . ?
N1 C2 1.402(11) . ?
N1 C4 1.451(13) . ?
N2 C3 1.342(13) . ?
N2 C1 1.362(12) . ?
N2 C5 1.472(13) . ?
C2 C3 1.360(14) . ?
C2 C6 1.469(13) . ?

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 C1 180.0 . 3_665 ?
C1 N1 C2 109.7(7) . . ?
C1 N1 C4 123.9(7) . . ?
C2 N1 C4 126.2(7) . . ?
C3 N2 C1 111.1(8) . . ?
C3 N2 C5 124.4(9) . . ?
C1 N2 C5 124.5(8) . . ?
N1 C1 N2 105.6(7) . . ?
N1 C1 Au1 129.5(7) . . ?
N2 C1 Au1 124.9(6) . . ?
C3 C2 N1 106.0(8) . . ?
C3 C2 C6 126.2(10) . . ?
N1 C2 C6 127.6(9) . . ?
N2 C3 C2 107.4(10) . . ?
O2 C6 O1 125.5(9) . . ?
O2 C6 C2 115.9(10) . . ?
O1 C6 C2 118.5(8) . . ?

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 -1.2(10) . . . . ?
C4 N1 C1 N2 -177.6(7) . . . . ?
C2 N1 C1 Au1 178.4(6) . . . . ?
C4 N1 C1 Au1 1.9(12) . . . . ?
C3 N2 C1 N1 0.4(10) . . . . ?
C5 N2 C1 N1 -178.8(9) . . . . ?
C3 N2 C1 Au1 -179.2(6) . . . . ?
C5 N2 C1 Au1 1.6(13) . . . . ?
C1 N1 C2 C3 1.5(10) . . . . ?
C4 N1 C2 C3 177.9(8) . . . . ?
C1 N1 C2 C6 176.6(9) . . . . ?
C4 N1 C2 C6 -7.0(14) . . . . ?
C1 N2 C3 C2 0.6(11) . . . . ?
C5 N2 C3 C2 179.7(9) . . . . ?
N1 C2 C3 N2 -1.2(10) . . . . ?
C6 C2 C3 N2 -176.4(9) . . . . ?
C3 C2 C6 O2 -15.1(14) . . . . ?
N1 C2 C6 O2 170.7(8) . . . . ?
C3 C2 C6 O1 165.1(9) . . . . ?
N1 C2 C6 O1 -9.1(14) . . . . ?

_refine_diff_density_max         2.224
_refine_diff_density_min         -0.923
_refine_diff_density_rms         0.171

