# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_nd1852
_database_code_depnum_ccdc_archive 'CCDC 2152030'
loop_
_audit_author_name
_audit_author_address
'Allen Oliver'
;University of Notre Dame
United States of America
;
_audit_update_record             
;
2022-02-14 deposited with the CCDC.	2022-04-29 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         'C18 H28 N3 O3, Au Cl4'
_chemical_formula_sum            'C18 H28 Au Cl4 N3 O3'
_chemical_formula_weight         673.20

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Au Au -2.0133 8.8022 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   7.0697(5)
_cell_length_b                   12.8591(8)
_cell_length_c                   13.3357(9)
_cell_angle_alpha                87.564(2)
_cell_angle_beta                 80.1017(19)
_cell_angle_gamma                88.5666(19)
_cell_volume                     1193.03(14)
_cell_formula_units_Z            2
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    8661
_cell_measurement_theta_min      2.17
_cell_measurement_theta_max      26.79

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.874
_exptl_crystal_F_000             656
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.094
_exptl_crystal_size_mid          0.035
_exptl_crystal_size_min          0.033
_exptl_absorpt_coefficient_mu    6.637
_shelx_estimated_absorpt_T_min   0.574
_shelx_estimated_absorpt_T_max   0.811
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.6873
_exptl_absorpt_correction_T_max  0.8721
_exptl_absorpt_process_details   'SADABS (Krause et al., 2015)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_monochromator     'Bruker TRIUMPH curved-graphite'
_diffrn_measurement_device_type  'Bruker APEX-II'
_diffrn_measurement_method       'combination of ω and φ-scans '
_diffrn_detector_area_resol_mean 8.33
_diffrn_reflns_number            34220
_diffrn_reflns_av_unetI/netI     0.0503
_diffrn_reflns_av_R_equivalents  0.0532
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.551
_diffrn_reflns_theta_max         30.560
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             7286
_reflns_number_gt                6065
_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       'Bruker APEX-3 (Bruker, 2015)'
_computing_cell_refinement       'Bruker SAINT (Bruker, 2015)'
_computing_data_reduction        'Bruker SAINT (Bruker, 2015)'
_computing_structure_solution    'SHELXT-2014/5 (Sheldrick, 2015a)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015b)'
_computing_molecular_graphics    'Bruker XP (Bruker, 2015)'
_computing_publication_material  'CIFTAB (Sheldrick, 2008)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0240P)²+0.0136P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_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         7286
_refine_ls_number_parameters     284
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0488
_refine_ls_R_factor_gt           0.0320
_refine_ls_wR_factor_ref         0.0561
_refine_ls_wR_factor_gt          0.0525
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_restrained_S_all      1.020
_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 0.24248(2) 0.80100(2) 0.30963(2) 0.01670(4) Uani 1 1 d . . . . .
Cl1 Cl 0.20530(12) 0.93986(6) 0.41351(7) 0.02495(18) Uani 1 1 d . . . . .
Cl2 Cl 0.28566(11) 0.66084(7) 0.20920(6) 0.02374(17) Uani 1 1 d . . . . .
Cl3 Cl 0.22945(11) 0.69191(7) 0.45051(6) 0.02310(17) Uani 1 1 d . . . . .
Cl4 Cl 0.24442(12) 0.91096(7) 0.17098(7) 0.02682(19) Uani 1 1 d . . . . .
O1 O 0.6594(4) 0.6537(2) -0.1283(2) 0.0444(8) Uani 1 1 d . . . . .
O2 O 0.7199(3) 1.22140(18) 0.3091(2) 0.0240(6) Uani 1 1 d . . . . .
H2O H 0.725(8) 1.283(4) 0.321(4) 0.09(2) Uiso 1 1 d . . . . .
O3 O 0.7628(3) 0.40749(17) 0.31717(19) 0.0229(5) Uani 1 1 d . . . . .
N1 N 0.5688(5) 0.7750(3) -0.0116(2) 0.0273(7) Uani 1 1 d . . . . .
H1N H 0.480(6) 0.799(3) 0.033(3) 0.047(14) Uiso 1 1 d . . . . .
N2 N 0.8600(4) 1.0660(2) 0.3136(2) 0.0194(6) Uani 1 1 d . . . . .
H2N H 0.952(5) 1.036(3) 0.314(3) 0.024(11) Uiso 1 1 d . . . . .
N3 N 0.6243(4) 0.5614(2) 0.3563(2) 0.0172(6) Uani 1 1 d . . . . .
H3N H 0.521(5) 0.593(3) 0.376(3) 0.022(10) Uiso 1 1 d . . . . .
C1 C 0.7691(4) 0.8095(3) 0.1137(3) 0.0188(7) Uani 1 1 d . . . . .
C2 C 0.7407(4) 0.9045(2) 0.1611(3) 0.0186(7) Uani 1 1 d . . . . .
C3 C 0.7228(4) 0.9066(2) 0.2680(2) 0.0154(6) Uani 1 1 d . . . . .
C4 C 0.7427(4) 0.8147(2) 0.3261(2) 0.0143(6) Uani 1 1 d . . . . .
C5 C 0.7792(4) 0.7202(2) 0.2769(2) 0.0160(6) Uani 1 1 d . . . . .
C6 C 0.7881(4) 0.7169(2) 0.1705(3) 0.0183(7) Uani 1 1 d . . . . .
C7 C 0.7621(5) 0.8034(3) 0.0008(3) 0.0265(8) Uani 1 1 d . . . . .
H7A H 0.795356 0.871602 -0.034332 0.032 Uiso 1 1 calc R U . . .
H7B H 0.856565 0.750695 -0.029921 0.032 Uiso 1 1 calc R U . . .
C8 C 0.5331(6) 0.6988(3) -0.0711(3) 0.0306(8) Uani 1 1 d . . . . .
C9 C 0.3232(6) 0.6726(4) -0.0617(3) 0.0462(12) Uani 1 1 d . . . . .
H9A H 0.244854 0.722966 -0.018564 0.069 Uiso 1 1 calc R U . . .
H9B H 0.301964 0.602408 -0.030926 0.069 Uiso 1 1 calc R U . . .
H9C H 0.286866 0.675616 -0.129423 0.069 Uiso 1 1 calc R U . . .
C10 C 0.7290(5) 1.0048(3) 0.0994(3) 0.0280(8) Uani 1 1 d . . . . .
H10A H 0.721632 1.063761 0.144215 0.042 Uiso 1 1 calc R U . . .
H10B H 0.614144 1.004932 0.067409 0.042 Uiso 1 1 calc R U . . .
H10C H 0.843478 1.010805 0.046592 0.042 Uiso 1 1 calc R U . . .
C11 C 0.6819(4) 1.0090(2) 0.3191(3) 0.0201(7) Uani 1 1 d . . . . .
H11A H 0.590256 1.051029 0.285119 0.024 Uiso 1 1 calc R U . . .
H11B H 0.622657 0.996303 0.391289 0.024 Uiso 1 1 calc R U . . .
C12 C 0.8715(5) 1.1676(2) 0.3109(2) 0.0176(6) Uani 1 1 d . . . . .
C13 C 1.0606(5) 1.2166(3) 0.3093(3) 0.0247(7) Uani 1 1 d . . . . .
H13A H 1.157109 1.162561 0.318208 0.037 Uiso 1 1 calc R U . . .
H13B H 1.049888 1.265236 0.364766 0.037 Uiso 1 1 calc R U . . .
H13C H 1.099235 1.254466 0.243925 0.037 Uiso 1 1 calc R U . . .
C14 C 0.7203(5) 0.8190(2) 0.4410(3) 0.0215(7) Uani 1 1 d . . . . .
H14A H 0.775410 0.755379 0.468290 0.032 Uiso 1 1 calc R U . . .
H14B H 0.583679 0.824676 0.470335 0.032 Uiso 1 1 calc R U . . .
H14C H 0.787368 0.879604 0.458607 0.032 Uiso 1 1 calc R U . . .
C15 C 0.8044(4) 0.6192(2) 0.3362(3) 0.0197(7) Uani 1 1 d . . . . .
H15A H 0.906690 0.576074 0.296843 0.024 Uiso 1 1 calc R U . . .
H15B H 0.844330 0.634413 0.401574 0.024 Uiso 1 1 calc R U . . .
C16 C 0.6110(5) 0.4615(2) 0.3436(2) 0.0171(6) Uani 1 1 d . . . . .
C17 C 0.4175(5) 0.4151(3) 0.3567(3) 0.0245(7) Uani 1 1 d . . . . .
H17A H 0.321926 0.463523 0.391998 0.037 Uiso 1 1 calc R U . . .
H17B H 0.416812 0.349524 0.396952 0.037 Uiso 1 1 calc R U . . .
H17C H 0.385981 0.401653 0.289697 0.037 Uiso 1 1 calc R U . . .
C18 C 0.8149(5) 0.6131(3) 0.1196(3) 0.0248(8) Uani 1 1 d . . . . .
H18A H 0.823233 0.624508 0.045806 0.037 Uiso 1 1 calc R U . . .
H18B H 0.705349 0.568805 0.146078 0.037 Uiso 1 1 calc R U . . .
H18C H 0.933379 0.578996 0.133863 0.037 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 Cl2 2.2744(8) . ?
Au1 Cl4 2.2779(9) . ?
Au1 Cl3 2.2866(8) . ?
Au1 Cl1 2.2887(8) . ?
O1 C8 1.221(5) . ?
O2 C12 1.265(4) . ?
O2 H2O 0.82(6) . ?
O3 C16 1.269(4) . ?
N1 C8 1.342(5) . ?
N1 C7 1.462(4) . ?
N1 H1N 0.85(4) . ?
N2 C12 1.309(4) . ?
N2 C11 1.462(4) . ?
N2 H2N 0.75(4) . ?
N3 C16 1.311(4) . ?
N3 C15 1.469(4) . ?
N3 H3N 0.83(4) . ?
C1 C2 1.394(5) . ?
C1 C6 1.400(5) . ?
C1 C7 1.520(5) . ?
C2 C3 1.410(5) . ?
C2 C10 1.508(4) . ?
C3 C4 1.403(4) . ?
C3 C11 1.507(4) . ?
C4 C5 1.402(4) . ?
C4 C14 1.516(4) . ?
C5 C6 1.412(4) . ?
C5 C15 1.515(4) . ?
C6 C18 1.516(4) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.513(5) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.489(4) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.486(4) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 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
Cl2 Au1 Cl4 91.07(3) . . ?
Cl2 Au1 Cl3 89.63(3) . . ?
Cl4 Au1 Cl3 178.01(3) . . ?
Cl2 Au1 Cl1 178.31(3) . . ?
Cl4 Au1 Cl1 90.21(3) . . ?
Cl3 Au1 Cl1 89.13(3) . . ?
C12 O2 H2O 117(4) . . ?
C8 N1 C7 123.5(3) . . ?
C8 N1 H1N 120(3) . . ?
C7 N1 H1N 114(3) . . ?
C12 N2 C11 124.7(3) . . ?
C12 N2 H2N 116(3) . . ?
C11 N2 H2N 119(3) . . ?
C16 N3 C15 124.7(3) . . ?
C16 N3 H3N 116(2) . . ?
C15 N3 H3N 120(2) . . ?
C2 C1 C6 120.7(3) . . ?
C2 C1 C7 120.4(3) . . ?
C6 C1 C7 118.6(3) . . ?
C1 C2 C3 119.5(3) . . ?
C1 C2 C10 120.7(3) . . ?
C3 C2 C10 119.8(3) . . ?
C4 C3 C2 120.6(3) . . ?
C4 C3 C11 120.4(3) . . ?
C2 C3 C11 119.1(3) . . ?
C5 C4 C3 119.3(3) . . ?
C5 C4 C14 121.2(3) . . ?
C3 C4 C14 119.4(3) . . ?
C4 C5 C6 120.4(3) . . ?
C4 C5 C15 121.2(3) . . ?
C6 C5 C15 118.3(3) . . ?
C1 C6 C5 119.4(3) . . ?
C1 C6 C18 120.9(3) . . ?
C5 C6 C18 119.6(3) . . ?
N1 C7 C1 109.1(3) . . ?
N1 C7 H7A 109.9 . . ?
C1 C7 H7A 109.9 . . ?
N1 C7 H7B 109.9 . . ?
C1 C7 H7B 109.9 . . ?
H7A C7 H7B 108.3 . . ?
O1 C8 N1 123.0(4) . . ?
O1 C8 C9 122.4(4) . . ?
N1 C8 C9 114.6(4) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C2 C10 H10A 109.5 . . ?
C2 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C2 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N2 C11 C3 110.1(3) . . ?
N2 C11 H11A 109.6 . . ?
C3 C11 H11A 109.6 . . ?
N2 C11 H11B 109.6 . . ?
C3 C11 H11B 109.6 . . ?
H11A C11 H11B 108.2 . . ?
O2 C12 N2 118.4(3) . . ?
O2 C12 C13 121.8(3) . . ?
N2 C12 C13 119.8(3) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C4 C14 H14A 109.5 . . ?
C4 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C4 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N3 C15 C5 110.6(2) . . ?
N3 C15 H15A 109.5 . . ?
C5 C15 H15A 109.5 . . ?
N3 C15 H15B 109.5 . . ?
C5 C15 H15B 109.5 . . ?
H15A C15 H15B 108.1 . . ?
O3 C16 N3 119.4(3) . . ?
O3 C16 C17 121.6(3) . . ?
N3 C16 C17 118.9(3) . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C6 C18 H18A 109.5 . . ?
C6 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C6 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 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
C6 C1 C2 C3 -2.8(5) . . . . ?
C7 C1 C2 C3 171.8(3) . . . . ?
C6 C1 C2 C10 177.3(3) . . . . ?
C7 C1 C2 C10 -8.2(5) . . . . ?
C1 C2 C3 C4 3.2(4) . . . . ?
C10 C2 C3 C4 -176.9(3) . . . . ?
C1 C2 C3 C11 -176.9(3) . . . . ?
C10 C2 C3 C11 3.1(4) . . . . ?
C2 C3 C4 C5 -0.5(4) . . . . ?
C11 C3 C4 C5 179.5(3) . . . . ?
C2 C3 C4 C14 -179.3(3) . . . . ?
C11 C3 C4 C14 0.7(4) . . . . ?
C3 C4 C5 C6 -2.6(4) . . . . ?
C14 C4 C5 C6 176.2(3) . . . . ?
C3 C4 C5 C15 179.2(3) . . . . ?
C14 C4 C5 C15 -2.0(4) . . . . ?
C2 C1 C6 C5 -0.3(4) . . . . ?
C7 C1 C6 C5 -174.9(3) . . . . ?
C2 C1 C6 C18 178.7(3) . . . . ?
C7 C1 C6 C18 4.1(4) . . . . ?
C4 C5 C6 C1 3.0(4) . . . . ?
C15 C5 C6 C1 -178.7(3) . . . . ?
C4 C5 C6 C18 -176.0(3) . . . . ?
C15 C5 C6 C18 2.2(4) . . . . ?
C8 N1 C7 C1 -131.0(4) . . . . ?
C2 C1 C7 N1 -94.9(4) . . . . ?
C6 C1 C7 N1 79.8(4) . . . . ?
C7 N1 C8 O1 -7.9(6) . . . . ?
C7 N1 C8 C9 172.0(3) . . . . ?
C12 N2 C11 C3 150.6(3) . . . . ?
C4 C3 C11 N2 98.0(3) . . . . ?
C2 C3 C11 N2 -82.0(4) . . . . ?
C11 N2 C12 O2 -2.9(5) . . . . ?
C11 N2 C12 C13 177.7(3) . . . . ?
C16 N3 C15 C5 134.2(3) . . . . ?
C4 C5 C15 N3 97.6(3) . . . . ?
C6 C5 C15 N3 -80.6(4) . . . . ?
C15 N3 C16 O3 3.9(5) . . . . ?
C15 N3 C16 C17 -173.8(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O2 H2O O3 0.82(6) 1.62(6) 2.429(3) 167(6) 1_565 yes
N1 H1N Cl4 0.85(4) 2.70(5) 3.533(3) 168(4) . yes
N2 H2N Cl1 0.75(4) 2.66(4) 3.332(3) 151(4) 1_655 yes
N3 H3N Cl3 0.83(4) 2.48(4) 3.306(3) 173(3) . yes

_refine_diff_density_max         1.714
_refine_diff_density_min         -1.493
_refine_diff_density_rms         0.156



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichloromethane / methanol / diethyl ether'
####################################################################### 
# 
# 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_nd1903
_database_code_depnum_ccdc_archive 'CCDC 2152032'
loop_
_audit_author_name
_audit_author_address
'Allen Oliver'
;University of Notre Dame
United States of America
;
_audit_update_record             
;
2022-02-14 deposited with the CCDC.	2022-04-29 downloaded from the CCDC.
;

_vrf_PLAT410_nd1903              
;
RESPONSE: These two hydrogen atoms are both located on methylene carbon atoms. 
The H atom position is geometrically calculated. Furthermore, inspection of the 
Fourier difference map reveals that these two H atoms are indeed in the
correct location. They are just, surprisingly, spatially close.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H34 N3 O3, Au Cl4'
_chemical_formula_sum            'C21 H34 Au Cl4 N3 O3'
_chemical_formula_weight         715.28

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Au Au -2.0133 8.8022 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   12.3290(9)
_cell_length_b                   16.7583(13)
_cell_length_c                   13.2907(10)
_cell_angle_alpha                90
_cell_angle_beta                 102.9930(10)
_cell_angle_gamma                90
_cell_volume                     2675.7(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    9904
_cell_measurement_theta_min      2.37
_cell_measurement_theta_max      30.43

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.776
_exptl_crystal_F_000             1408
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.236
_exptl_crystal_size_mid          0.212
_exptl_crystal_size_min          0.123
_exptl_absorpt_coefficient_mu    5.925
_shelx_estimated_absorpt_T_min   0.335
_shelx_estimated_absorpt_T_max   0.529
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.1901
_exptl_absorpt_correction_T_max  0.4968
_exptl_absorpt_process_details   'SADABS (Krause et al., 2015)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Kappa X8-APEX-II'
_diffrn_measurement_method       'combination of ω and φ-scans '
_diffrn_detector_area_resol_mean 8.33
_diffrn_reflns_number            55484
_diffrn_reflns_av_unetI/netI     0.0117
_diffrn_reflns_av_R_equivalents  0.0193
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.987
_diffrn_reflns_theta_max         30.465
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             8132
_reflns_number_gt                6347
_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       'Bruker APEX-3 (Bruker, 2015)'
_computing_cell_refinement       'Bruker SAINT (Bruker, 2015)'
_computing_data_reduction        'Bruker SAINT (Bruker, 2015)'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015)'
_computing_molecular_graphics    'Bruker XP (Bruker, 2015)'
_computing_publication_material  'CIFTAB (Sheldrick, 2008)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0092P)²+3.2502P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_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         8132
_refine_ls_number_parameters     314
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0269
_refine_ls_R_factor_gt           0.0167
_refine_ls_wR_factor_ref         0.0380
_refine_ls_wR_factor_gt          0.0346
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_restrained_S_all      1.075
_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
Au1 Au 0.500000 0.500000 0.000000 0.01551(2) Uani 1 2 d S . P . .
Au2 Au 0.500000 0.500000 0.500000 0.01575(2) Uani 1 2 d S . P . .
Cl1 Cl 0.60580(4) 0.39936(3) 0.08716(4) 0.02977(11) Uani 1 1 d . . . . .
Cl2 Cl 0.38831(4) 0.40725(3) -0.09695(5) 0.03028(11) Uani 1 1 d . . . . .
Cl3 Cl 0.39026(4) 0.60804(3) 0.44403(4) 0.02317(9) Uani 1 1 d . . . . .
Cl4 Cl 0.56370(4) 0.50004(3) 0.35128(4) 0.02419(9) Uani 1 1 d . . . . .
O1 O 0.00453(10) 0.59277(7) 0.27152(10) 0.0173(3) Uani 1 1 d . . . . .
H1O H -0.070(3) 0.637(2) 0.246(3) 0.087(12) Uiso 1 1 d . . . . .
O2 O 0.46884(11) 0.18112(8) 0.72666(11) 0.0202(3) Uani 1 1 d . . . . .
O3 O 0.64669(11) 0.18826(8) 0.28034(12) 0.0230(3) Uani 1 1 d . . . . .
N1 N 0.05466(13) 0.46560(9) 0.27963(13) 0.0162(3) Uani 1 1 d . . . . .
H1N H 0.043(2) 0.4261(15) 0.2694(19) 0.025(7) Uiso 1 1 d . . . . .
N2 N 0.40357(13) 0.30181(9) 0.66975(12) 0.0148(3) Uani 1 1 d . . . . .
H2N H 0.4152(18) 0.3497(14) 0.6702(17) 0.019(6) Uiso 1 1 d . . . . .
N3 N 0.55551(13) 0.30208(9) 0.30518(13) 0.0163(3) Uani 1 1 d . . . . .
H3N H 0.564(2) 0.3523(16) 0.326(2) 0.035(7) Uiso 1 1 d . . . . .
C1 C 0.23787(13) 0.41212(10) 0.36276(14) 0.0134(3) Uani 1 1 d . . . . .
C2 C 0.23429(13) 0.37575(10) 0.45752(13) 0.0130(3) Uani 1 1 d . . . . .
C3 C 0.30048(13) 0.30828(10) 0.48986(13) 0.0124(3) Uani 1 1 d . . . . .
C4 C 0.36671(13) 0.27544(9) 0.42726(13) 0.0122(3) Uani 1 1 d . . . . .
C5 C 0.36717(13) 0.31114(10) 0.33193(13) 0.0129(3) Uani 1 1 d . . . . .
C6 C 0.30477(14) 0.38040(10) 0.29945(14) 0.0137(3) Uani 1 1 d . . . . .
C7 C 0.17010(14) 0.48635(10) 0.32938(15) 0.0165(3) Uani 1 1 d . . . . .
H7A H 0.170770 0.520499 0.390302 0.020 Uiso 1 1 calc R U . . .
H7B H 0.203797 0.516955 0.280448 0.020 Uiso 1 1 calc R U . . .
C8 C -0.02279(15) 0.51957(11) 0.25247(14) 0.0159(3) Uani 1 1 d . . . . .
C9 C -0.13825(16) 0.49586(12) 0.20218(18) 0.0258(4) Uani 1 1 d . . . . .
H9A H -0.188700 0.511367 0.246201 0.039 Uiso 1 1 calc R U . . .
H9B H -0.141547 0.437917 0.191967 0.039 Uiso 1 1 calc R U . . .
H9C H -0.160727 0.522634 0.135170 0.039 Uiso 1 1 calc R U . . .
C10 C 0.15593(16) 0.40582(11) 0.52202(15) 0.0200(4) Uani 1 1 d . . . . .
H10A H 0.139206 0.462823 0.506162 0.024 Uiso 1 1 calc R U . . .
H10B H 0.192925 0.401623 0.596090 0.024 Uiso 1 1 calc R U . . .
C11 C 0.04651(16) 0.35835(15) 0.50154(16) 0.0280(5) Uani 1 1 d . . . . .
H11A H -0.004291 0.382400 0.540032 0.042 Uiso 1 1 calc R U . . .
H11B H 0.061949 0.302999 0.524013 0.042 Uiso 1 1 calc R U . . .
H11C H 0.012092 0.359394 0.427527 0.042 Uiso 1 1 calc R U . . .
C12 C 0.30565(14) 0.27208(10) 0.59572(13) 0.0140(3) Uani 1 1 d . . . . .
H12A H 0.237477 0.286214 0.619363 0.017 Uiso 1 1 calc R U . . .
H12B H 0.309436 0.213204 0.591361 0.017 Uiso 1 1 calc R U . . .
C13 C 0.48001(14) 0.25467(10) 0.72782(14) 0.0143(3) Uani 1 1 d . . . . .
C14 C 0.57954(16) 0.29488(12) 0.79456(15) 0.0214(4) Uani 1 1 d . . . . .
H14A H 0.647632 0.268592 0.785318 0.032 Uiso 1 1 calc R U . . .
H14B H 0.575105 0.291125 0.867112 0.032 Uiso 1 1 calc R U . . .
H14C H 0.580797 0.351153 0.774795 0.032 Uiso 1 1 calc R U . . .
C15 C 0.43383(15) 0.20048(10) 0.46103(14) 0.0156(3) Uani 1 1 d . . . . .
H15A H 0.460746 0.201060 0.537045 0.019 Uiso 1 1 calc R U . . .
H15B H 0.499664 0.199862 0.429961 0.019 Uiso 1 1 calc R U . . .
C16 C 0.36488(18) 0.12453(11) 0.42888(17) 0.0234(4) Uani 1 1 d . . . . .
H16A H 0.410908 0.077493 0.452221 0.035 Uiso 1 1 calc R U . . .
H16B H 0.339523 0.123132 0.353526 0.035 Uiso 1 1 calc R U . . .
H16C H 0.300241 0.124524 0.460376 0.035 Uiso 1 1 calc R U . . .
C17 C 0.44042(14) 0.27536(11) 0.26637(14) 0.0156(3) Uani 1 1 d . . . . .
H17A H 0.436924 0.216395 0.269026 0.019 Uiso 1 1 calc R U . . .
H17B H 0.413747 0.292273 0.193633 0.019 Uiso 1 1 calc R U . . .
C18 C 0.64667(14) 0.25953(10) 0.30983(14) 0.0152(3) Uani 1 1 d . . . . .
C19 C 0.75572(15) 0.29933(12) 0.35303(18) 0.0241(4) Uani 1 1 d . . . . .
H19A H 0.803049 0.263564 0.402559 0.036 Uiso 1 1 calc R U . . .
H19B H 0.742996 0.348789 0.387996 0.036 Uiso 1 1 calc R U . . .
H19C H 0.792612 0.311727 0.296838 0.036 Uiso 1 1 calc R U . . .
C20 C 0.30703(17) 0.41776(12) 0.19596(15) 0.0223(4) Uani 1 1 d . . . . .
H20A H 0.380477 0.407670 0.179980 0.027 Uiso 1 1 calc R U . . .
H20B H 0.297630 0.476229 0.200403 0.027 Uiso 1 1 calc R U . . .
C21 C 0.21574(19) 0.38471(18) 0.10859(17) 0.0388(6) Uani 1 1 d . . . . .
H21A H 0.221639 0.409284 0.043124 0.058 Uiso 1 1 calc R U . . .
H21B H 0.142696 0.396872 0.122377 0.058 Uiso 1 1 calc R U . . .
H21C H 0.224331 0.326757 0.104220 0.058 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 Cl2 2.2748(5) 3_665 ?
Au1 Cl2 2.2748(5) . ?
Au1 Cl1 2.2822(5) 3_665 ?
Au1 Cl1 2.2822(5) . ?
Au2 Cl3 2.2823(5) 3_666 ?
Au2 Cl3 2.2824(5) . ?
Au2 Cl4 2.2852(5) . ?
Au2 Cl4 2.2852(5) 3_666 ?
O1 C8 1.282(2) . ?
O1 H1O 1.18(4) . ?
O2 C13 1.240(2) . ?
O3 C18 1.257(2) . ?
N1 C8 1.306(2) . ?
N1 C7 1.470(2) . ?
N1 H1N 0.68(3) . ?
N2 C13 1.334(2) . ?
N2 C12 1.463(2) . ?
N2 H2N 0.82(2) . ?
N3 C18 1.321(2) . ?
N3 C17 1.467(2) . ?
N3 H3N 0.89(3) . ?
C1 C6 1.408(2) . ?
C1 C2 1.409(2) . ?
C1 C7 1.509(2) . ?
C2 C3 1.404(2) . ?
C2 C10 1.515(2) . ?
C3 C4 1.403(2) . ?
C3 C12 1.520(2) . ?
C4 C5 1.402(2) . ?
C4 C15 1.516(2) . ?
C5 C6 1.406(2) . ?
C5 C17 1.513(2) . ?
C6 C20 1.517(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.484(2) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C11 1.537(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.502(2) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 C16 1.537(3) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C19 1.495(2) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 C21 1.528(3) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 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
Cl2 Au1 Cl2 180.0 3_665 . ?
Cl2 Au1 Cl1 89.24(2) 3_665 3_665 ?
Cl2 Au1 Cl1 90.76(2) . 3_665 ?
Cl2 Au1 Cl1 90.76(2) 3_665 . ?
Cl2 Au1 Cl1 89.24(2) . . ?
Cl1 Au1 Cl1 180.0 3_665 . ?
Cl3 Au2 Cl3 180.0 3_666 . ?
Cl3 Au2 Cl4 89.328(19) 3_666 . ?
Cl3 Au2 Cl4 90.671(18) . . ?
Cl3 Au2 Cl4 90.672(18) 3_666 3_666 ?
Cl3 Au2 Cl4 89.329(18) . 3_666 ?
Cl4 Au2 Cl4 180.0 . 3_666 ?
C8 O1 H1O 113.3(18) . . ?
C8 N1 C7 122.30(15) . . ?
C8 N1 H1N 120(2) . . ?
C7 N1 H1N 118(2) . . ?
C13 N2 C12 123.79(15) . . ?
C13 N2 H2N 118.6(16) . . ?
C12 N2 H2N 117.2(16) . . ?
C18 N3 C17 126.69(15) . . ?
C18 N3 H3N 117.2(17) . . ?
C17 N3 H3N 116.1(17) . . ?
C6 C1 C2 120.74(15) . . ?
C6 C1 C7 119.71(16) . . ?
C2 C1 C7 119.54(16) . . ?
C3 C2 C1 119.29(16) . . ?
C3 C2 C10 119.69(16) . . ?
C1 C2 C10 120.94(15) . . ?
C4 C3 C2 120.68(16) . . ?
C4 C3 C12 118.91(14) . . ?
C2 C3 C12 120.35(15) . . ?
C5 C4 C3 119.33(15) . . ?
C5 C4 C15 120.54(15) . . ?
C3 C4 C15 120.10(15) . . ?
C4 C5 C6 121.10(16) . . ?
C4 C5 C17 118.40(15) . . ?
C6 C5 C17 120.45(16) . . ?
C5 C6 C1 118.81(16) . . ?
C5 C6 C20 119.92(16) . . ?
C1 C6 C20 121.23(15) . . ?
N1 C7 C1 110.70(14) . . ?
N1 C7 H7A 109.5 . . ?
C1 C7 H7A 109.5 . . ?
N1 C7 H7B 109.5 . . ?
C1 C7 H7B 109.5 . . ?
H7A C7 H7B 108.1 . . ?
O1 C8 N1 117.69(16) . . ?
O1 C8 C9 121.86(16) . . ?
N1 C8 C9 120.45(17) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C2 C10 C11 111.95(16) . . ?
C2 C10 H10A 109.2 . . ?
C11 C10 H10A 109.2 . . ?
C2 C10 H10B 109.2 . . ?
C11 C10 H10B 109.2 . . ?
H10A C10 H10B 107.9 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N2 C12 C3 110.06(14) . . ?
N2 C12 H12A 109.6 . . ?
C3 C12 H12A 109.6 . . ?
N2 C12 H12B 109.6 . . ?
C3 C12 H12B 109.6 . . ?
H12A C12 H12B 108.2 . . ?
O2 C13 N2 121.28(17) . . ?
O2 C13 C14 121.79(16) . . ?
N2 C13 C14 116.93(16) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C4 C15 C16 111.90(15) . . ?
C4 C15 H15A 109.2 . . ?
C16 C15 H15A 109.2 . . ?
C4 C15 H15B 109.2 . . ?
C16 C15 H15B 109.2 . . ?
H15A C15 H15B 107.9 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N3 C17 C5 109.40(14) . . ?
N3 C17 H17A 109.8 . . ?
C5 C17 H17A 109.8 . . ?
N3 C17 H17B 109.8 . . ?
C5 C17 H17B 109.8 . . ?
H17A C17 H17B 108.2 . . ?
O3 C18 N3 123.93(16) . . ?
O3 C18 C19 118.71(16) . . ?
N3 C18 C19 117.36(16) . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C6 C20 C21 112.26(17) . . ?
C6 C20 H20A 109.2 . . ?
C21 C20 H20A 109.2 . . ?
C6 C20 H20B 109.2 . . ?
C21 C20 H20B 109.2 . . ?
H20A C20 H20B 107.9 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 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
C6 C1 C2 C3 1.6(2) . . . . ?
C7 C1 C2 C3 -177.82(15) . . . . ?
C6 C1 C2 C10 -175.30(16) . . . . ?
C7 C1 C2 C10 5.3(2) . . . . ?
C1 C2 C3 C4 -2.2(2) . . . . ?
C10 C2 C3 C4 174.68(15) . . . . ?
C1 C2 C3 C12 174.83(15) . . . . ?
C10 C2 C3 C12 -8.3(2) . . . . ?
C2 C3 C4 C5 0.6(2) . . . . ?
C12 C3 C4 C5 -176.50(15) . . . . ?
C2 C3 C4 C15 -177.31(15) . . . . ?
C12 C3 C4 C15 5.6(2) . . . . ?
C3 C4 C5 C6 1.7(2) . . . . ?
C15 C4 C5 C6 179.63(15) . . . . ?
C3 C4 C5 C17 179.18(15) . . . . ?
C15 C4 C5 C17 -2.9(2) . . . . ?
C4 C5 C6 C1 -2.4(2) . . . . ?
C17 C5 C6 C1 -179.76(15) . . . . ?
C4 C5 C6 C20 179.91(16) . . . . ?
C17 C5 C6 C20 2.5(2) . . . . ?
C2 C1 C6 C5 0.7(2) . . . . ?
C7 C1 C6 C5 -179.92(15) . . . . ?
C2 C1 C6 C20 178.39(16) . . . . ?
C7 C1 C6 C20 -2.2(2) . . . . ?
C8 N1 C7 C1 173.63(18) . . . . ?
C6 C1 C7 N1 97.40(19) . . . . ?
C2 C1 C7 N1 -83.2(2) . . . . ?
C7 N1 C8 O1 -0.6(3) . . . . ?
C7 N1 C8 C9 179.85(18) . . . . ?
C3 C2 C10 C11 -81.4(2) . . . . ?
C1 C2 C10 C11 95.5(2) . . . . ?
C13 N2 C12 C3 -125.91(18) . . . . ?
C4 C3 C12 N2 80.50(19) . . . . ?
C2 C3 C12 N2 -96.61(18) . . . . ?
C12 N2 C13 O2 -4.3(3) . . . . ?
C12 N2 C13 C14 175.89(17) . . . . ?
C5 C4 C15 C16 -91.9(2) . . . . ?
C3 C4 C15 C16 86.0(2) . . . . ?
C18 N3 C17 C5 142.57(18) . . . . ?
C4 C5 C17 N3 -79.91(19) . . . . ?
C6 C5 C17 N3 97.55(18) . . . . ?
C17 N3 C18 O3 0.2(3) . . . . ?
C17 N3 C18 C19 -179.73(18) . . . . ?
C5 C6 C20 C21 90.3(2) . . . . ?
C1 C6 C20 C21 -87.4(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O1 H1O O3 1.18(4) 1.26(4) 2.4360(18) 177(4) 2 yes
N1 H1N O2 0.68(3) 2.04(3) 2.707(2) 166(3) 4_565 yes
N2 H2N Cl4 0.82(2) 2.55(2) 3.3644(16) 173(2) 3_666 yes
N3 H3N Cl4 0.89(3) 2.50(3) 3.3709(16) 168(2) . yes

_refine_diff_density_max         0.475
_refine_diff_density_min         -0.773
_refine_diff_density_rms         0.085



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichloromethane / methanol / diethyl ether'
####################################################################### 
# 
# 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_nd1854_sq
_database_code_depnum_ccdc_archive 'CCDC 2152031'
loop_
_audit_author_name
_audit_author_address
'Allen Oliver'
;University of Notre Dame
United States of America
;
_audit_update_record             
;
2022-02-14 deposited with the CCDC.	2022-04-29 downloaded from the CCDC.
;

_vrf_THETM01_nd1854_sq           
;
RESPONSE: Due to a rapid drop-off in intensity with increasing
sin(theta)/(lambda) data were truncated at 0.9 \%A. Disorder
is likely the cause of this issue. This does not affect the 
final connectivity of the structure.
;

_vrf_PLAT342_nd1854_sq           
;
RESPONSE: There is disorder within the molecules that is exhibited
through exaggerated displacement parameters. This motion affects the 
precision of the bond measurements. However, the strutcure is correct.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '4(C19 H28 N3 O3), 4(Au Br4), C4 H10 O'
_chemical_formula_sum            'C76 H122 Au4 Br16 N12 O13'
_chemical_formula_weight         3478.27

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 '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'

_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                   11.433(3)
_cell_length_b                   14.321(4)
_cell_length_c                   19.606(6)
_cell_angle_alpha                71.990(5)
_cell_angle_beta                 82.849(5)
_cell_angle_gamma                74.244(4)
_cell_volume                     2935.2(15)
_cell_formula_units_Z            1
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    3026
_cell_measurement_theta_min      2.28
_cell_measurement_theta_max      21.43

_exptl_crystal_description       blade
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.968
_exptl_crystal_F_000             1642
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.137
_exptl_crystal_size_mid          0.093
_exptl_crystal_size_min          0.016
_exptl_absorpt_coefficient_mu    10.480
_shelx_estimated_absorpt_T_min   0.328
_shelx_estimated_absorpt_T_max   0.850
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.4190
_exptl_absorpt_correction_T_max  08718
_exptl_absorpt_process_details   'SADABS (Krause et al., 2015)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_monochromator     'Bruker TRIUMPH curved-graphite'
_diffrn_measurement_device_type  'Bruker PHOTON-II'
_diffrn_measurement_method       'combination of ω and φ-scans '
_diffrn_detector_area_resol_mean 7.41
_diffrn_reflns_number            29675
_diffrn_reflns_av_unetI/netI     0.1036
_diffrn_reflns_av_R_equivalents  0.0973
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.093
_diffrn_reflns_theta_max         23.256
_diffrn_reflns_theta_full        23.256
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             8423
_reflns_number_gt                5556
_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.
 
 Structure factors included contributions from the .fab file.
 
 _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       'Bruker APEX-3 (Bruker, 2015)'
_computing_cell_refinement       'Bruker SAINT (Bruker, 2015)'
_computing_data_reduction        'Bruker SAINT (Bruker, 2015)'
_computing_structure_solution    'SHELXT-2014/5 (Sheldrick, 2015a)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015b)'
_computing_molecular_graphics    'Bruker XP (Bruker, 2015)'
_computing_publication_material  'CIFTAB (Sheldrick, 2008)'
_refine_special_details          
;Due to a rpaid decrease in intensity with increasing sin(theta)/lambda
data were truncated at 0.9 Å resolution. Furthermore, to maintain a 
reasonable structure similarity restraints were applied to all 
displacement parameters. Finally, unresolvable solvent disorder
was treated through the SQUEEZE routine, as implemented in PLATON 
(Spek, 2009).

The charge balancing hydrogen atoms were located in ideal positions
where two amide oxygens were proximal to each other on neighboring
molecules. Reasonable locations were found on O3 and O5.,SQUEEZE
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1096P)²+127.0232P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_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         8423
_refine_ls_number_parameters     555
_refine_ls_number_restraints     292
_refine_ls_R_factor_all          0.1279
_refine_ls_R_factor_gt           0.0837
_refine_ls_wR_factor_ref         0.2383
_refine_ls_wR_factor_gt          0.2106
_refine_ls_goodness_of_fit_ref   0.977
_refine_ls_restrained_S_all      0.969
_refine_ls_shift/su_max          0.054
_refine_ls_shift/su_mean         0.002

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 0.79610(7) 0.78108(6) 0.15108(5) 0.0372(3) Uani 1 1 d . . . . .
Br1 Br 0.88195(17) 0.61267(16) 0.22529(13) 0.0382(6) Uani 1 1 d . . . . .
Br2 Br 0.7109(2) 0.83372(19) 0.25690(16) 0.0527(7) Uani 1 1 d . . . . .
Br3 Br 0.8747(2) 0.7274(2) 0.04546(14) 0.0536(7) Uani 1 1 d . . . . .
Br4 Br 0.7182(2) 0.95094(19) 0.07364(18) 0.0672(9) Uani 1 1 d . . . . .
Au2 Au 0.75899(9) 0.66143(7) 0.64648(5) 0.0460(3) Uani 1 1 d . . . . .
Br5 Br 0.6263(2) 0.63564(19) 0.75163(15) 0.0549(7) Uani 1 1 d . . . . .
Br6 Br 0.5954(3) 0.6728(3) 0.57602(17) 0.0813(10) Uani 1 1 d . . . . .
Br7 Br 0.8936(3) 0.6913(3) 0.54209(17) 0.0822(10) Uani 1 1 d . . . . .
Br8 Br 0.9224(3) 0.6437(3) 0.71889(18) 0.0793(10) Uani 1 1 d . . . . .
O1 O 0.2533(15) 1.0755(12) 0.1842(12) 0.065(4) Uani 1 1 d . U . . .
O2 O 0.7550(11) 0.3899(9) 0.0945(8) 0.031(3) Uani 1 1 d . U . . .
O3 O 0.6560(16) 0.4599(16) 0.4498(10) 0.070(5) Uani 1 1 d . U . . .
H3O H 0.706114 0.422496 0.480966 0.105 Uiso 1 1 calc R U . . .
N1 N 0.4235(17) 0.9792(14) 0.1459(12) 0.051(3) Uani 1 1 d . U . . .
H1 H 0.502212 0.971682 0.136224 0.061 Uiso 1 1 calc R U . . .
N2 N 0.5790(13) 0.5084(11) 0.0873(9) 0.025(2) Uani 1 1 d . U . . .
H2 H 0.499176 0.522896 0.086819 0.030 Uiso 1 1 calc R U . . .
N3 N 0.6252(16) 0.6068(16) 0.3644(11) 0.048(3) Uani 1 1 d . U . . .
H3 H 0.649040 0.662723 0.343036 0.057 Uiso 1 1 calc R U . . .
C1 C 0.4412(18) 0.7989(16) 0.1628(14) 0.038(2) Uani 1 1 d . U . . .
C2 C 0.5056(17) 0.7486(15) 0.1125(13) 0.034(3) Uani 1 1 d . U . . .
C3 C 0.5713(16) 0.6467(15) 0.1378(13) 0.030(2) Uani 1 1 d . U . . .
C4 C 0.5710(17) 0.5964(15) 0.2123(13) 0.033(3) Uani 1 1 d . U . . .
C5 C 0.5073(18) 0.6528(16) 0.2607(13) 0.037(2) Uani 1 1 d . U . . .
C6 C 0.4440(18) 0.7521(16) 0.2360(14) 0.038(3) Uani 1 1 d . U . . .
C7 C 0.3681(19) 0.9059(16) 0.1372(15) 0.045(3) Uani 1 1 d . U . . .
H7A H 0.353379 0.921566 0.085641 0.054 Uiso 1 1 calc R U . . .
H7B H 0.288009 0.912008 0.163556 0.054 Uiso 1 1 calc R U . . .
C8 C 0.362(2) 1.0582(18) 0.1678(17) 0.058(3) Uani 1 1 d . U . . .
C9 C 0.443(2) 1.1259(19) 0.1753(18) 0.069(5) Uani 1 1 d . U . . .
H9A H 0.395988 1.196811 0.163244 0.103 Uiso 1 1 calc R U . . .
H9B H 0.514547 1.119191 0.142557 0.103 Uiso 1 1 calc R U . . .
H9C H 0.468383 1.104319 0.224806 0.103 Uiso 1 1 calc R U . . .
C10 C 0.508(2) 0.8037(16) 0.0335(13) 0.042(4) Uani 1 1 d . U . . .
H10A H 0.446856 0.788879 0.010280 0.063 Uiso 1 1 calc R U . . .
H10B H 0.588774 0.781283 0.011995 0.063 Uiso 1 1 calc R U . . .
H10C H 0.489786 0.876811 0.026868 0.063 Uiso 1 1 calc R U . . .
C11 C 0.6362(16) 0.5912(14) 0.0856(12) 0.029(3) Uani 1 1 d . U . . .
H11A H 0.722657 0.562051 0.097761 0.035 Uiso 1 1 calc R U . . .
H11B H 0.633344 0.638922 0.036630 0.035 Uiso 1 1 calc R U . . .
C12 C 0.6392(17) 0.4158(14) 0.0895(12) 0.028(3) Uani 1 1 d . U . . .
C13 C 0.5731(16) 0.3415(14) 0.0895(12) 0.028(4) Uani 1 1 d . U . . .
H13A H 0.613064 0.304712 0.054890 0.042 Uiso 1 1 calc R U . . .
H13B H 0.489189 0.376380 0.076151 0.042 Uiso 1 1 calc R U . . .
H13C H 0.572798 0.293475 0.137611 0.042 Uiso 1 1 calc R U . . .
C14 C 0.6436(18) 0.4894(15) 0.2394(13) 0.038(4) Uani 1 1 d . U . . .
H14A H 0.662606 0.475584 0.289459 0.058 Uiso 1 1 calc R U . . .
H14B H 0.719317 0.479373 0.210080 0.058 Uiso 1 1 calc R U . . .
H14C H 0.596333 0.443183 0.236323 0.058 Uiso 1 1 calc R U . . .
C15 C 0.5124(19) 0.5996(18) 0.3398(13) 0.042(3) Uani 1 1 d . U . . .
H15A H 0.440866 0.632134 0.365754 0.051 Uiso 1 1 calc R U . . .
H15B H 0.512058 0.527717 0.349037 0.051 Uiso 1 1 calc R U . . .
C16 C 0.694(2) 0.540(2) 0.4143(15) 0.054(3) Uani 1 1 d . U . . .
C17 C 0.816(2) 0.552(2) 0.4294(15) 0.059(5) Uani 1 1 d . U . . .
H17A H 0.877812 0.487860 0.433917 0.088 Uiso 1 1 calc R U . . .
H17B H 0.808353 0.570467 0.474098 0.088 Uiso 1 1 calc R U . . .
H17C H 0.840411 0.605228 0.389662 0.088 Uiso 1 1 calc R U . . .
C18 C 0.374(2) 0.8098(17) 0.2874(14) 0.046(4) Uani 1 1 d . U . . .
H18A H 0.391080 0.768546 0.336932 0.068 Uiso 1 1 calc R U . . .
H18B H 0.286212 0.824748 0.280598 0.068 Uiso 1 1 calc R U . . .
H18C H 0.397872 0.873334 0.278027 0.068 Uiso 1 1 calc R U . . .
O4 O 0.6681(11) 0.4580(10) 0.9332(8) 0.031(3) Uani 1 1 d . U . . .
O5 O 1.1463(12) -0.2124(9) 0.8953(8) 0.032(3) Uani 1 1 d . U . . .
H5O H 1.177188 -0.273752 0.898197 0.049 Uiso 1 1 calc R U . . .
O6 O 0.7938(17) 0.3499(16) 0.5401(10) 0.071(5) Uani 1 1 d . U . . .
N4 N 0.8259(14) 0.3979(11) 0.8635(9) 0.028(3) Uani 1 1 d . U . . .
H4 H 0.902303 0.394556 0.848449 0.034 Uiso 1 1 calc R U . . .
N5 N 0.9742(15) -0.0948(12) 0.8665(9) 0.032(3) Uani 1 1 d . U . . .
H5 H 0.898243 -0.078718 0.854330 0.038 Uiso 1 1 calc R U . . .
N6 N 0.895(2) 0.1984(18) 0.5919(12) 0.065(3) Uani 1 1 d . U . . .
H6 H 0.902797 0.132848 0.601613 0.078 Uiso 1 1 calc R U . . .
C21 C 0.8460(17) 0.2572(15) 0.8115(11) 0.028(2) Uani 1 1 d . U . . .
C22 C 0.8999(17) 0.1615(15) 0.8578(11) 0.028(2) Uani 1 1 d . U . . .
C23 C 0.9690(18) 0.0903(15) 0.8293(12) 0.032(2) Uani 1 1 d . U . . .
C24 C 0.9963(19) 0.1082(16) 0.7553(12) 0.036(3) Uani 1 1 d . U . . .
C25 C 0.9466(19) 0.2047(17) 0.7088(13) 0.039(3) Uani 1 1 d . U . . .
C26 C 0.8697(18) 0.2825(15) 0.7378(12) 0.033(3) Uani 1 1 d . U . . .
C27 C 0.7579(17) 0.3402(15) 0.8428(12) 0.029(3) Uani 1 1 d . U . . .
H27A H 0.699611 0.386148 0.806235 0.035 Uiso 1 1 calc R U . . .
H27B H 0.710963 0.307496 0.885095 0.035 Uiso 1 1 calc R U . . .
C28 C 0.7720(17) 0.4563(15) 0.9058(12) 0.029(3) Uani 1 1 d . U . . .
C29 C 0.8469(18) 0.5209(16) 0.9219(13) 0.035(4) Uani 1 1 d . U . . .
H29A H 0.798465 0.591124 0.912924 0.052 Uiso 1 1 calc R U . . .
H29B H 0.920992 0.518898 0.890736 0.052 Uiso 1 1 calc R U . . .
H29C H 0.868926 0.493975 0.972240 0.052 Uiso 1 1 calc R U . . .
C30 C 0.8771(19) 0.1425(17) 0.9373(11) 0.036(4) Uani 1 1 d . U . . .
H30A H 0.824453 0.095427 0.955005 0.053 Uiso 1 1 calc R U . . .
H30B H 0.837201 0.206661 0.947832 0.053 Uiso 1 1 calc R U . . .
H30C H 0.954645 0.113067 0.961117 0.053 Uiso 1 1 calc R U . . .
C31 C 1.0238(19) -0.0158(14) 0.8770(12) 0.034(3) Uani 1 1 d . U . . .
H31A H 1.112908 -0.032588 0.867222 0.041 Uiso 1 1 calc R U . . .
H31B H 1.008902 -0.015818 0.927896 0.041 Uiso 1 1 calc R U . . .
C32 C 1.0382(18) -0.1872(14) 0.8745(12) 0.029(3) Uani 1 1 d . U . . .
C33 C 0.9827(18) -0.2624(14) 0.8639(12) 0.031(4) Uani 1 1 d . U . . .
H33A H 1.026758 -0.287906 0.824560 0.047 Uiso 1 1 calc R U . . .
H33B H 0.897486 -0.230847 0.852067 0.047 Uiso 1 1 calc R U . . .
H33C H 0.986851 -0.318770 0.908084 0.047 Uiso 1 1 calc R U . . .
C34 C 1.076(2) 0.0277(16) 0.7224(13) 0.040(4) Uani 1 1 d . U . . .
H34A H 1.035925 0.027253 0.680993 0.060 Uiso 1 1 calc R U . . .
H34B H 1.086973 -0.038860 0.758181 0.060 Uiso 1 1 calc R U . . .
H34C H 1.154876 0.042941 0.706717 0.060 Uiso 1 1 calc R U . . .
C35 C 0.973(2) 0.231(2) 0.6287(14) 0.054(3) Uani 1 1 d . U . . .
H35A H 0.962263 0.304940 0.609031 0.065 Uiso 1 1 calc R U . . .
H35B H 1.059273 0.197989 0.619110 0.065 Uiso 1 1 calc R U . . .
C36 C 0.815(3) 0.258(2) 0.5460(16) 0.069(4) Uani 1 1 d . U . . .
C37 C 0.741(3) 0.213(3) 0.5149(18) 0.085(6) Uani 1 1 d . U . . .
H37A H 0.658238 0.257204 0.508393 0.127 Uiso 1 1 calc R U . . .
H37B H 0.737012 0.146373 0.547487 0.127 Uiso 1 1 calc R U . . .
H37C H 0.777405 0.205735 0.468379 0.127 Uiso 1 1 calc R U . . .
C38 C 0.8276(19) 0.3885(16) 0.6908(13) 0.044(5) Uani 1 1 d . U . . .
H38A H 0.792261 0.433757 0.720654 0.067 Uiso 1 1 calc R U . . .
H38B H 0.766002 0.391077 0.659190 0.067 Uiso 1 1 calc R U . . .
H38C H 0.896827 0.410115 0.661629 0.067 Uiso 1 1 calc R U . . .
O1S O 0.282(3) 0.906(2) 0.6181(16) 0.042(5) Uiso 0.5 1 d . U P . .
C1S C 0.362(5) 1.033(4) 0.565(3) 0.054(9) Uiso 0.5 1 d . U P . .
H1SA H 0.430898 1.060746 0.564717 0.081 Uiso 0.5 1 calc R U P . .
H1SB H 0.361224 1.020445 0.518079 0.081 Uiso 0.5 1 calc R U P . .
H1SC H 0.285875 1.080596 0.572541 0.081 Uiso 0.5 1 calc R U P . .
C2S C 0.372(4) 0.949(4) 0.614(3) 0.049(6) Uiso 0.5 1 d . U P . .
H2SA H 0.374355 0.962127 0.660834 0.059 Uiso 0.5 1 calc R U P . .
H2SB H 0.449629 0.902035 0.606426 0.059 Uiso 0.5 1 calc R U P . .
C3S C 0.295(4) 0.811(3) 0.683(2) 0.038(6) Uiso 0.5 1 d . U P . .
H3SA H 0.370299 0.759941 0.676385 0.045 Uiso 0.5 1 calc R U P . .
H3SB H 0.302877 0.829366 0.726956 0.045 Uiso 0.5 1 calc R U P . .
C4S C 0.203(4) 0.773(3) 0.691(2) 0.035(8) Uiso 0.5 1 d . U P . .
H4SB H 0.213389 0.713074 0.733197 0.053 Uiso 0.5 1 calc R U P . .
H4SC H 0.129105 0.823605 0.698899 0.053 Uiso 0.5 1 calc R U P . .
H4SD H 0.196425 0.754285 0.648403 0.053 Uiso 0.5 1 calc R U P . .


_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 Br1 2.408(2) . ?
Au1 Br3 2.415(3) . ?
Au1 Br2 2.426(3) . ?
Au1 Br4 2.427(3) . ?
Au2 Br5 2.396(3) . ?
Au2 Br8 2.398(3) . ?
Au2 Br6 2.402(3) . ?
Au2 Br7 2.403(3) . ?
O1 C8 1.22(3) . ?
O2 C12 1.28(2) . ?
O3 C16 1.29(3) . ?
O3 H3O 0.8400 . ?
N1 C8 1.32(3) . ?
N1 C7 1.43(3) . ?
N1 H1 0.8800 . ?
N2 C12 1.31(2) . ?
N2 C11 1.49(2) . ?
N2 H2 0.8800 . ?
N3 C16 1.30(3) . ?
N3 C15 1.47(3) . ?
N3 H3 0.8800 . ?
C1 C2 1.42(3) . ?
C1 C6 1.38(3) . ?
C1 C7 1.49(3) . ?
C2 C3 1.41(3) . ?
C2 C10 1.51(3) . ?
C3 C4 1.42(3) . ?
C3 C11 1.49(3) . ?
C4 C5 1.44(3) . ?
C4 C14 1.49(3) . ?
C5 C6 1.37(3) . ?
C5 C15 1.50(3) . ?
C6 C18 1.52(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.56(3) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.46(3) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.53(3) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
O4 C28 1.24(2) . ?
O5 C32 1.27(2) . ?
O5 H5O 0.8400 . ?
O6 C36 1.24(3) . ?
N4 C28 1.34(3) . ?
N4 C27 1.45(2) . ?
N4 H4 0.8800 . ?
N5 C32 1.30(2) . ?
N5 C31 1.47(3) . ?
N5 H5 0.8800 . ?
N6 C36 1.30(3) . ?
N6 C35 1.46(3) . ?
N6 H6 0.8800 . ?
C21 C26 1.39(3) . ?
C21 C22 1.41(3) . ?
C21 C27 1.57(3) . ?
C22 C23 1.33(3) . ?
C22 C30 1.50(3) . ?
C23 C24 1.40(3) . ?
C23 C31 1.53(3) . ?
C24 C25 1.41(3) . ?
C24 C34 1.52(3) . ?
C25 C26 1.44(3) . ?
C25 C35 1.51(3) . ?
C26 C38 1.50(3) . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
C28 C29 1.54(3) . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 0.9800 . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?
C32 C33 1.46(3) . ?
C33 H33A 0.9800 . ?
C33 H33B 0.9800 . ?
C33 H33C 0.9800 . ?
C34 H34A 0.9800 . ?
C34 H34B 0.9800 . ?
C34 H34C 0.9800 . ?
C35 H35A 0.9900 . ?
C35 H35B 0.9900 . ?
C36 C37 1.48(4) . ?
C37 H37A 0.9800 . ?
C37 H37B 0.9800 . ?
C37 H37C 0.9800 . ?
C38 H38A 0.9800 . ?
C38 H38B 0.9800 . ?
C38 H38C 0.9800 . ?
O1S C2S 1.33(5) . ?
O1S C3S 1.54(5) . ?
C1S C2S 1.27(6) . ?
C1S H1SA 0.9800 . ?
C1S H1SB 0.9800 . ?
C1S H1SC 0.9800 . ?
C2S H2SA 0.9900 . ?
C2S H2SB 0.9900 . ?
C3S C4S 1.28(6) . ?
C3S H3SA 0.9900 . ?
C3S H3SB 0.9900 . ?
C4S H4SB 0.9800 . ?
C4S H4SC 0.9800 . ?
C4S H4SD 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
Br1 Au1 Br3 89.62(9) . . ?
Br1 Au1 Br2 90.47(9) . . ?
Br3 Au1 Br2 178.12(8) . . ?
Br1 Au1 Br4 177.50(9) . . ?
Br3 Au1 Br4 88.88(12) . . ?
Br2 Au1 Br4 91.10(11) . . ?
Br5 Au2 Br8 90.09(12) . . ?
Br5 Au2 Br6 89.09(11) . . ?
Br8 Au2 Br6 177.92(13) . . ?
Br5 Au2 Br7 178.25(12) . . ?
Br8 Au2 Br7 88.85(12) . . ?
Br6 Au2 Br7 92.02(12) . . ?
C16 O3 H3O 109.5 . . ?
C8 N1 C7 123(2) . . ?
C8 N1 H1 118.5 . . ?
C7 N1 H1 118.5 . . ?
C12 N2 C11 124.6(15) . . ?
C12 N2 H2 117.7 . . ?
C11 N2 H2 117.7 . . ?
C16 N3 C15 127(2) . . ?
C16 N3 H3 116.4 . . ?
C15 N3 H3 116.4 . . ?
C2 C1 C6 121.9(19) . . ?
C2 C1 C7 120(2) . . ?
C6 C1 C7 118(2) . . ?
C1 C2 C3 119(2) . . ?
C1 C2 C10 120.8(19) . . ?
C3 C2 C10 120(2) . . ?
C2 C3 C4 119.9(19) . . ?
C2 C3 C11 120(2) . . ?
C4 C3 C11 120.3(18) . . ?
C3 C4 C5 118.4(19) . . ?
C3 C4 C14 119.9(19) . . ?
C5 C4 C14 121(2) . . ?
C6 C5 C4 122(2) . . ?
C6 C5 C15 121(2) . . ?
C4 C5 C15 117.8(19) . . ?
C5 C6 C1 119(2) . . ?
C5 C6 C18 121(2) . . ?
C1 C6 C18 119.7(19) . . ?
N1 C7 C1 114.4(18) . . ?
N1 C7 H7A 108.7 . . ?
C1 C7 H7A 108.7 . . ?
N1 C7 H7B 108.7 . . ?
C1 C7 H7B 108.7 . . ?
H7A C7 H7B 107.6 . . ?
O1 C8 N1 124(2) . . ?
O1 C8 C9 122(2) . . ?
N1 C8 C9 114(2) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.4 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C2 C10 H10A 109.5 . . ?
C2 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C2 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C3 C11 N2 110.5(16) . . ?
C3 C11 H11A 109.6 . . ?
N2 C11 H11A 109.6 . . ?
C3 C11 H11B 109.6 . . ?
N2 C11 H11B 109.6 . . ?
H11A C11 H11B 108.1 . . ?
O2 C12 N2 119.7(16) . . ?
O2 C12 C13 120.6(17) . . ?
N2 C12 C13 119.7(16) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C4 C14 H14A 109.5 . . ?
C4 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C4 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N3 C15 C5 107.6(18) . . ?
N3 C15 H15A 110.2 . . ?
C5 C15 H15A 110.2 . . ?
N3 C15 H15B 110.2 . . ?
C5 C15 H15B 110.2 . . ?
H15A C15 H15B 108.5 . . ?
O3 C16 N3 117(2) . . ?
O3 C16 C17 121(2) . . ?
N3 C16 C17 122(2) . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C6 C18 H18A 109.5 . . ?
C6 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C6 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C32 O5 H5O 109.5 . . ?
C28 N4 C27 119.6(16) . . ?
C28 N4 H4 120.2 . . ?
C27 N4 H4 120.2 . . ?
C32 N5 C31 122.7(17) . . ?
C32 N5 H5 118.7 . . ?
C31 N5 H5 118.7 . . ?
C36 N6 C35 125(3) . . ?
C36 N6 H6 117.4 . . ?
C35 N6 H6 117.3 . . ?
C26 C21 C22 122.3(19) . . ?
C26 C21 C27 117.5(18) . . ?
C22 C21 C27 120.2(19) . . ?
C23 C22 C21 119(2) . . ?
C23 C22 C30 122.0(19) . . ?
C21 C22 C30 119.1(18) . . ?
C22 C23 C24 123(2) . . ?
C22 C23 C31 121(2) . . ?
C24 C23 C31 116.6(19) . . ?
C23 C24 C25 119(2) . . ?
C23 C24 C34 123(2) . . ?
C25 C24 C34 118(2) . . ?
C24 C25 C26 120(2) . . ?
C24 C25 C35 122(2) . . ?
C26 C25 C35 118(2) . . ?
C21 C26 C25 117.4(19) . . ?
C21 C26 C38 121.7(19) . . ?
C25 C26 C38 121(2) . . ?
N4 C27 C21 110.4(15) . . ?
N4 C27 H27A 109.6 . . ?
C21 C27 H27A 109.6 . . ?
N4 C27 H27B 109.6 . . ?
C21 C27 H27B 109.6 . . ?
H27A C27 H27B 108.1 . . ?
O4 C28 N4 123.1(17) . . ?
O4 C28 C29 120.0(18) . . ?
N4 C28 C29 116.9(17) . . ?
C28 C29 H29A 109.5 . . ?
C28 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C28 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C22 C30 H30A 109.5 . . ?
C22 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
C22 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
N5 C31 C23 113.6(16) . . ?
N5 C31 H31A 108.8 . . ?
C23 C31 H31A 108.8 . . ?
N5 C31 H31B 108.8 . . ?
C23 C31 H31B 108.8 . . ?
H31A C31 H31B 107.7 . . ?
O5 C32 N5 119.2(17) . . ?
O5 C32 C33 120.9(16) . . ?
N5 C32 C33 119.8(18) . . ?
C32 C33 H33A 109.5 . . ?
C32 C33 H33B 109.5 . . ?
H33A C33 H33B 109.5 . . ?
C32 C33 H33C 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
C24 C34 H34A 109.5 . . ?
C24 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
C24 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
N6 C35 C25 113(2) . . ?
N6 C35 H35A 109.0 . . ?
C25 C35 H35A 109.1 . . ?
N6 C35 H35B 109.1 . . ?
C25 C35 H35B 109.0 . . ?
H35A C35 H35B 107.8 . . ?
O6 C36 N6 117(3) . . ?
O6 C36 C37 124(3) . . ?
N6 C36 C37 118(3) . . ?
C36 C37 H37A 109.4 . . ?
C36 C37 H37B 109.5 . . ?
H37A C37 H37B 109.5 . . ?
C36 C37 H37C 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
C26 C38 H38A 109.5 . . ?
C26 C38 H38B 109.5 . . ?
H38A C38 H38B 109.5 . . ?
C26 C38 H38C 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
C2S O1S C3S 110(3) . . ?
C2S C1S H1SA 109.5 . . ?
C2S C1S H1SB 109.5 . . ?
H1SA C1S H1SB 109.5 . . ?
C2S C1S H1SC 109.5 . . ?
H1SA C1S H1SC 109.5 . . ?
H1SB C1S H1SC 109.5 . . ?
C1S C2S O1S 114(5) . . ?
C1S C2S H2SA 108.8 . . ?
O1S C2S H2SA 108.8 . . ?
C1S C2S H2SB 108.8 . . ?
O1S C2S H2SB 108.8 . . ?
H2SA C2S H2SB 107.7 . . ?
C4S C3S O1S 111(4) . . ?
C4S C3S H3SA 109.5 . . ?
O1S C3S H3SA 109.5 . . ?
C4S C3S H3SB 109.5 . . ?
O1S C3S H3SB 109.5 . . ?
H3SA C3S H3SB 108.1 . . ?
C3S C4S H4SB 109.5 . . ?
C3S C4S H4SC 109.5 . . ?
H4SB C4S H4SC 109.5 . . ?
C3S C4S H4SD 109.5 . . ?
H4SB C4S H4SD 109.5 . . ?
H4SC C4S H4SD 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
C6 C1 C2 C3 2(3) . . . . ?
C7 C1 C2 C3 -178.2(17) . . . . ?
C6 C1 C2 C10 -175.7(18) . . . . ?
C7 C1 C2 C10 4(3) . . . . ?
C1 C2 C3 C4 1(3) . . . . ?
C10 C2 C3 C4 178.4(17) . . . . ?
C1 C2 C3 C11 177.9(16) . . . . ?
C10 C2 C3 C11 -4(3) . . . . ?
C2 C3 C4 C5 -3(3) . . . . ?
C11 C3 C4 C5 180.0(16) . . . . ?
C2 C3 C4 C14 -178.1(17) . . . . ?
C11 C3 C4 C14 5(3) . . . . ?
C3 C4 C5 C6 2(3) . . . . ?
C14 C4 C5 C6 177.8(18) . . . . ?
C3 C4 C5 C15 -177.4(17) . . . . ?
C14 C4 C5 C15 -2(3) . . . . ?
C4 C5 C6 C1 0(3) . . . . ?
C15 C5 C6 C1 179.9(18) . . . . ?
C4 C5 C6 C18 177.9(18) . . . . ?
C15 C5 C6 C18 -2(3) . . . . ?
C2 C1 C6 C5 -2(3) . . . . ?
C7 C1 C6 C5 177.9(18) . . . . ?
C2 C1 C6 C18 179.7(18) . . . . ?
C7 C1 C6 C18 0(3) . . . . ?
C8 N1 C7 C1 -139(3) . . . . ?
C2 C1 C7 N1 -104(2) . . . . ?
C6 C1 C7 N1 76(3) . . . . ?
C7 N1 C8 O1 2(5) . . . . ?
C7 N1 C8 C9 178(2) . . . . ?
C2 C3 C11 N2 -113.2(19) . . . . ?
C4 C3 C11 N2 64(2) . . . . ?
C12 N2 C11 C3 -134(2) . . . . ?
C11 N2 C12 O2 4(3) . . . . ?
C11 N2 C12 C13 -178.8(19) . . . . ?
C16 N3 C15 C5 -146(2) . . . . ?
C6 C5 C15 N3 -95(2) . . . . ?
C4 C5 C15 N3 84(2) . . . . ?
C15 N3 C16 O3 -5(4) . . . . ?
C15 N3 C16 C17 174(2) . . . . ?
C26 C21 C22 C23 -5(3) . . . . ?
C27 C21 C22 C23 176.2(17) . . . . ?
C26 C21 C22 C30 175.4(18) . . . . ?
C27 C21 C22 C30 -3(3) . . . . ?
C21 C22 C23 C24 4(3) . . . . ?
C30 C22 C23 C24 -176.7(19) . . . . ?
C21 C22 C23 C31 -177.0(17) . . . . ?
C30 C22 C23 C31 3(3) . . . . ?
C22 C23 C24 C25 -1(3) . . . . ?
C31 C23 C24 C25 179.2(18) . . . . ?
C22 C23 C24 C34 179.7(19) . . . . ?
C31 C23 C24 C34 0(3) . . . . ?
C23 C24 C25 C26 0(3) . . . . ?
C34 C24 C25 C26 179.1(19) . . . . ?
C23 C24 C25 C35 179(2) . . . . ?
C34 C24 C25 C35 -2(3) . . . . ?
C22 C21 C26 C25 4(3) . . . . ?
C27 C21 C26 C25 -177.4(17) . . . . ?
C22 C21 C26 C38 -170.5(18) . . . . ?
C27 C21 C26 C38 8(3) . . . . ?
C24 C25 C26 C21 -1(3) . . . . ?
C35 C25 C26 C21 179.9(19) . . . . ?
C24 C25 C26 C38 173(2) . . . . ?
C35 C25 C26 C38 -6(3) . . . . ?
C28 N4 C27 C21 -165.0(18) . . . . ?
C26 C21 C27 N4 -92(2) . . . . ?
C22 C21 C27 N4 87(2) . . . . ?
C27 N4 C28 O4 6(3) . . . . ?
C27 N4 C28 C29 -176.2(18) . . . . ?
C32 N5 C31 C23 148(2) . . . . ?
C22 C23 C31 N5 113(2) . . . . ?
C24 C23 C31 N5 -67(2) . . . . ?
C31 N5 C32 O5 3(3) . . . . ?
C31 N5 C32 C33 179(2) . . . . ?
C36 N6 C35 C25 115(3) . . . . ?
C24 C25 C35 N6 83(3) . . . . ?
C26 C25 C35 N6 -98(3) . . . . ?
C35 N6 C36 O6 -9(5) . . . . ?
C35 N6 C36 C37 -178(3) . . . . ?
C3S O1S C2S C1S -175(4) . . . . ?
C2S O1S C3S C4S 174(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O3 H3O O6 0.84 1.55 2.39(3) 177.0 . yes
N1 H1 Br4 0.88 2.60 3.46(2) 164.3 . yes
N2 H2 O4 0.88 1.93 2.793(19) 166.6 2_666 yes
N3 H3 Br2 0.88 2.73 3.60(2) 170.7 . yes
O5 H5O O2 0.84 1.60 2.441(18) 175.8 2_756 yes
N4 H4 Br1 0.88 2.69 3.557(16) 167.5 2_766 yes
N5 H5 O1 0.88 1.96 2.81(2) 163.7 2_666 yes

_refine_diff_density_max         5.955
_refine_diff_density_min         -3.123
_refine_diff_density_rms         0.275




_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichloromethane / methanol / diethyl ether'
####################################################################### 
# 
# 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_nd1904
_database_code_depnum_ccdc_archive 'CCDC 2152033'
loop_
_audit_author_name
_audit_author_address
'Allen Oliver'
;University of Notre Dame
United States of America
;
_audit_update_record             
;
2022-02-14 deposited with the CCDC.	2022-04-29 downloaded from the CCDC.
;
_vrf_PLAT410_nd1904              
;
RESPONSE: These two hydrogen atoms are both located on methylene carbon atoms. 
The H atom position is geometrically calculated. Furthermore, inspection of the 
Fourier difference map reveals that these two H atoms are indeed in the
correct location. They are just, surprisingly, spatially close.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H34 N3 O3, Au Br4'
_chemical_formula_sum            'C21 H34 Au Br4 N3 O3'
_chemical_formula_weight         893.12

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 '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'

_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                   12.5789(11)
_cell_length_b                   17.0609(15)
_cell_length_c                   13.3931(12)
_cell_angle_alpha                90
_cell_angle_beta                 103.800(2)
_cell_angle_gamma                90
_cell_volume                     2791.3(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    9881
_cell_measurement_theta_min      2.32
_cell_measurement_theta_max      30.61

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.125
_exptl_crystal_F_000             1696
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.189
_exptl_crystal_size_mid          0.149
_exptl_crystal_size_min          0.088
_exptl_absorpt_coefficient_mu    11.023
_shelx_estimated_absorpt_T_min   0.230
_shelx_estimated_absorpt_T_max   0.444
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.2843
_exptl_absorpt_correction_T_max  0.6116
_exptl_absorpt_process_details   'SADABS (Krause et al., 2015)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_monochromator     'Bruker TRIUMPH curved-graphite'
_diffrn_measurement_device_type  'Bruker APEX-II'
_diffrn_measurement_method       'combination of ω and φ-scans '
_diffrn_detector_area_resol_mean 8.33
_diffrn_reflns_number            99093
_diffrn_reflns_av_unetI/netI     0.0182
_diffrn_reflns_av_R_equivalents  0.0379
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.969
_diffrn_reflns_theta_max         30.649
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             8616
_reflns_number_gt                6586
_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       'Bruker APEX-3 (Bruker, 2015)'
_computing_cell_refinement       'Bruker SAINT (Bruker, 2015)'
_computing_data_reduction        'Bruker SAINT (Bruker, 2015)'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015)'
_computing_molecular_graphics    'Bruker XP (Bruker, 2015)'
_computing_publication_material  'CIFTAB (Sheldrick, 2008)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0185P)²+4.0502P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_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         8616
_refine_ls_number_parameters     310
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0373
_refine_ls_R_factor_gt           0.0211
_refine_ls_wR_factor_ref         0.0485
_refine_ls_wR_factor_gt          0.0438
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_restrained_S_all      1.022
_refine_ls_shift/su_max          0.002
_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 0.01476(3) Uani 1 2 d S . P . .
Au2 Au 0.500000 0.500000 0.500000 0.01737(3) Uani 1 2 d S . P . .
Br1 Br 0.61130(2) 0.39468(2) 0.09030(2) 0.02629(6) Uani 1 1 d . . . . .
Br2 Br 0.37777(2) 0.40327(2) -0.09736(2) 0.02683(6) Uani 1 1 d . . . . .
Br3 Br 0.38647(2) 0.61389(2) 0.44344(2) 0.02291(6) Uani 1 1 d . . . . .
Br4 Br 0.55847(2) 0.49856(2) 0.33989(2) 0.02426(6) Uani 1 1 d . . . . .
O1 O 0.01415(14) 0.58718(10) 0.27450(14) 0.0189(4) Uani 1 1 d . . . . .
H1O H -0.054180 0.622802 0.256772 0.028 Uiso 1 1 d R U . . .
O2 O 0.46380(15) 0.18030(10) 0.72801(15) 0.0213(4) Uani 1 1 d . . . . .
O3 O 0.63407(15) 0.18349(10) 0.27285(17) 0.0247(4) Uani 1 1 d . . . . .
N1 N 0.05834(17) 0.46141(12) 0.28052(17) 0.0166(4) Uani 1 1 d . . . . .
H1N H 0.042(2) 0.4144(18) 0.270(2) 0.020(8) Uiso 1 1 d . . . . .
N2 N 0.40278(17) 0.29909(12) 0.66851(16) 0.0152(4) Uani 1 1 d . . . . .
H2N H 0.415(2) 0.3450(19) 0.671(2) 0.024(8) Uiso 1 1 d . . . . .
N3 N 0.54487(17) 0.29379(12) 0.30101(18) 0.0171(4) Uani 1 1 d . . . . .
H3N H 0.554(3) 0.339(2) 0.322(3) 0.031(9) Uiso 1 1 d . . . . .
C1 C 0.23869(19) 0.40593(13) 0.35962(19) 0.0144(5) Uani 1 1 d . . . . .
C2 C 0.23668(19) 0.37195(13) 0.45496(18) 0.0145(4) Uani 1 1 d . . . . .
C3 C 0.30046(18) 0.30510(13) 0.48839(18) 0.0132(4) Uani 1 1 d . . . . .
C4 C 0.36286(18) 0.27104(13) 0.42618(18) 0.0130(4) Uani 1 1 d . . . . .
C5 C 0.36193(18) 0.30411(13) 0.33029(19) 0.0140(4) Uani 1 1 d . . . . .
C6 C 0.30135(19) 0.37247(13) 0.29646(19) 0.0152(5) Uani 1 1 d . . . . .
C7 C 0.1736(2) 0.47967(14) 0.3256(2) 0.0176(5) Uani 1 1 d . . . . .
H7A H 0.179054 0.514802 0.385481 0.021 Uiso 1 1 calc R U . . .
H7B H 0.204827 0.507496 0.274331 0.021 Uiso 1 1 calc R U . . .
C8 C -0.0163(2) 0.51570(14) 0.25713(19) 0.0173(5) Uani 1 1 d . . . . .
C9 C -0.1322(2) 0.49455(16) 0.2120(3) 0.0304(7) Uani 1 1 d . . . . .
H9A H -0.177753 0.512664 0.257389 0.046 Uiso 1 1 calc R U . . .
H9B H -0.138643 0.437506 0.204193 0.046 Uiso 1 1 calc R U . . .
H9C H -0.156744 0.519489 0.144474 0.046 Uiso 1 1 calc R U . . .
C10 C 0.1634(2) 0.40467(16) 0.5201(2) 0.0219(5) Uani 1 1 d . . . . .
H10A H 0.149109 0.460791 0.503325 0.026 Uiso 1 1 calc R U . . .
H10B H 0.201852 0.400925 0.593578 0.026 Uiso 1 1 calc R U . . .
C11 C 0.0538(2) 0.3608(2) 0.5025(2) 0.0295(6) Uani 1 1 d . . . . .
H11A H 0.007435 0.385866 0.542562 0.044 Uiso 1 1 calc R U . . .
H11B H 0.067234 0.306161 0.524430 0.044 Uiso 1 1 calc R U . . .
H11C H 0.016883 0.362430 0.429300 0.044 Uiso 1 1 calc R U . . .
C12 C 0.30543(19) 0.27061(14) 0.59412(18) 0.0150(4) Uani 1 1 d . . . . .
H12A H 0.238921 0.285710 0.616825 0.018 Uiso 1 1 calc R U . . .
H12B H 0.307687 0.212702 0.590464 0.018 Uiso 1 1 calc R U . . .
C13 C 0.4764(2) 0.25214(14) 0.72823(19) 0.0155(5) Uani 1 1 d . . . . .
C14 C 0.5744(2) 0.29105(16) 0.7968(2) 0.0211(5) Uani 1 1 d . . . . .
H14A H 0.641243 0.264359 0.789761 0.032 Uiso 1 1 calc R U . . .
H14B H 0.568751 0.287987 0.868388 0.032 Uiso 1 1 calc R U . . .
H14C H 0.577105 0.346142 0.776817 0.032 Uiso 1 1 calc R U . . .
C15 C 0.4285(2) 0.19730(14) 0.4612(2) 0.0175(5) Uani 1 1 d . . . . .
H15A H 0.454525 0.198066 0.537054 0.021 Uiso 1 1 calc R U . . .
H15B H 0.493464 0.196416 0.431658 0.021 Uiso 1 1 calc R U . . .
C16 C 0.3605(2) 0.12273(15) 0.4284(2) 0.0262(6) Uani 1 1 d . . . . .
H16A H 0.406682 0.076486 0.449209 0.039 Uiso 1 1 calc R U . . .
H16B H 0.332436 0.122637 0.353610 0.039 Uiso 1 1 calc R U . . .
H16C H 0.298978 0.121522 0.461632 0.039 Uiso 1 1 calc R U . . .
C17 C 0.43139(19) 0.26682(15) 0.2651(2) 0.0174(5) Uani 1 1 d . . . . .
H17A H 0.428395 0.209022 0.270448 0.021 Uiso 1 1 calc R U . . .
H17B H 0.402850 0.281552 0.192099 0.021 Uiso 1 1 calc R U . . .
C18 C 0.6344(2) 0.25336(14) 0.3026(2) 0.0158(5) Uani 1 1 d . . . . .
C19 C 0.7415(2) 0.29368(15) 0.3432(2) 0.0218(5) Uani 1 1 d . . . . .
H19A H 0.786580 0.262384 0.398845 0.033 Uiso 1 1 calc R U . . .
H19B H 0.728544 0.345503 0.369576 0.033 Uiso 1 1 calc R U . . .
H19C H 0.779601 0.299609 0.287789 0.033 Uiso 1 1 calc R U . . .
C20 C 0.3003(2) 0.40655(16) 0.1914(2) 0.0228(5) Uani 1 1 d . . . . .
H20A H 0.370470 0.394010 0.173656 0.027 Uiso 1 1 calc R U . . .
H20B H 0.294176 0.464314 0.194248 0.027 Uiso 1 1 calc R U . . .
C21 C 0.2058(3) 0.3747(2) 0.1074(2) 0.0381(8) Uani 1 1 d . . . . .
H21A H 0.209897 0.396496 0.040789 0.057 Uiso 1 1 calc R U . . .
H21B H 0.136016 0.389642 0.122525 0.057 Uiso 1 1 calc R U . . .
H21C H 0.210727 0.317386 0.105174 0.057 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 Br2 2.4148(3) . ?
Au1 Br2 2.4148(3) 3_665 ?
Au1 Br1 2.4173(3) 3_665 ?
Au1 Br1 2.4173(3) . ?
Au2 Br3 2.4234(3) 3_666 ?
Au2 Br3 2.4234(3) . ?
Au2 Br4 2.4274(3) . ?
Au2 Br4 2.4274(3) 3_666 ?
O1 C8 1.283(3) . ?
O1 H1O 1.0330 . ?
O2 C13 1.236(3) . ?
O3 C18 1.257(3) . ?
N1 C8 1.303(3) . ?
N1 C7 1.466(3) . ?
N1 H1N 0.83(3) . ?
N2 C13 1.336(3) . ?
N2 C12 1.465(3) . ?
N2 H2N 0.80(3) . ?
N3 C18 1.317(3) . ?
N3 C17 1.467(3) . ?
N3 H3N 0.82(3) . ?
C1 C6 1.407(3) . ?
C1 C2 1.408(3) . ?
C1 C7 1.511(3) . ?
C2 C3 1.405(3) . ?
C2 C10 1.518(3) . ?
C3 C4 1.400(3) . ?
C3 C12 1.521(3) . ?
C4 C5 1.400(3) . ?
C4 C15 1.516(3) . ?
C5 C6 1.408(3) . ?
C5 C17 1.515(3) . ?
C6 C20 1.520(4) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.483(4) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C11 1.537(4) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.505(3) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 C16 1.538(4) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C19 1.494(3) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 C21 1.529(4) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 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
Br2 Au1 Br2 180.0 . 3_665 ?
Br2 Au1 Br1 91.124(11) . 3_665 ?
Br2 Au1 Br1 88.876(11) 3_665 3_665 ?
Br2 Au1 Br1 88.876(12) . . ?
Br2 Au1 Br1 91.124(11) 3_665 . ?
Br1 Au1 Br1 180.0 3_665 . ?
Br3 Au2 Br3 180.000(14) 3_666 . ?
Br3 Au2 Br4 89.304(10) 3_666 . ?
Br3 Au2 Br4 90.696(10) . . ?
Br3 Au2 Br4 90.696(10) 3_666 3_666 ?
Br3 Au2 Br4 89.304(10) . 3_666 ?
Br4 Au2 Br4 180.0 . 3_666 ?
C8 O1 H1O 108.7 . . ?
C8 N1 C7 122.3(2) . . ?
C8 N1 H1N 120(2) . . ?
C7 N1 H1N 117(2) . . ?
C13 N2 C12 123.8(2) . . ?
C13 N2 H2N 118(2) . . ?
C12 N2 H2N 118(2) . . ?
C18 N3 C17 127.1(2) . . ?
C18 N3 H3N 116(2) . . ?
C17 N3 H3N 117(2) . . ?
C6 C1 C2 120.8(2) . . ?
C6 C1 C7 119.8(2) . . ?
C2 C1 C7 119.4(2) . . ?
C3 C2 C1 119.4(2) . . ?
C3 C2 C10 119.6(2) . . ?
C1 C2 C10 120.9(2) . . ?
C4 C3 C2 120.4(2) . . ?
C4 C3 C12 119.3(2) . . ?
C2 C3 C12 120.3(2) . . ?
C3 C4 C5 119.7(2) . . ?
C3 C4 C15 120.1(2) . . ?
C5 C4 C15 120.2(2) . . ?
C4 C5 C6 121.0(2) . . ?
C4 C5 C17 118.7(2) . . ?
C6 C5 C17 120.3(2) . . ?
C1 C6 C5 118.7(2) . . ?
C1 C6 C20 121.3(2) . . ?
C5 C6 C20 119.9(2) . . ?
N1 C7 C1 111.03(19) . . ?
N1 C7 H7A 109.4 . . ?
C1 C7 H7A 109.4 . . ?
N1 C7 H7B 109.4 . . ?
C1 C7 H7B 109.4 . . ?
H7A C7 H7B 108.0 . . ?
O1 C8 N1 117.7(2) . . ?
O1 C8 C9 121.8(2) . . ?
N1 C8 C9 120.5(2) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C2 C10 C11 112.2(2) . . ?
C2 C10 H10A 109.2 . . ?
C11 C10 H10A 109.2 . . ?
C2 C10 H10B 109.2 . . ?
C11 C10 H10B 109.2 . . ?
H10A C10 H10B 107.9 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N2 C12 C3 110.31(19) . . ?
N2 C12 H12A 109.6 . . ?
C3 C12 H12A 109.6 . . ?
N2 C12 H12B 109.6 . . ?
C3 C12 H12B 109.6 . . ?
H12A C12 H12B 108.1 . . ?
O2 C13 N2 121.5(2) . . ?
O2 C13 C14 121.7(2) . . ?
N2 C13 C14 116.8(2) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C4 C15 C16 111.9(2) . . ?
C4 C15 H15A 109.2 . . ?
C16 C15 H15A 109.2 . . ?
C4 C15 H15B 109.2 . . ?
C16 C15 H15B 109.2 . . ?
H15A C15 H15B 107.9 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N3 C17 C5 109.20(19) . . ?
N3 C17 H17A 109.8 . . ?
C5 C17 H17A 109.8 . . ?
N3 C17 H17B 109.8 . . ?
C5 C17 H17B 109.8 . . ?
H17A C17 H17B 108.3 . . ?
O3 C18 N3 123.6(2) . . ?
O3 C18 C19 119.1(2) . . ?
N3 C18 C19 117.3(2) . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C6 C20 C21 112.2(2) . . ?
C6 C20 H20A 109.2 . . ?
C21 C20 H20A 109.2 . . ?
C6 C20 H20B 109.2 . . ?
C21 C20 H20B 109.2 . . ?
H20A C20 H20B 107.9 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 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
C6 C1 C2 C3 1.8(3) . . . . ?
C7 C1 C2 C3 -177.6(2) . . . . ?
C6 C1 C2 C10 -175.9(2) . . . . ?
C7 C1 C2 C10 4.8(3) . . . . ?
C1 C2 C3 C4 -2.0(3) . . . . ?
C10 C2 C3 C4 175.7(2) . . . . ?
C1 C2 C3 C12 175.9(2) . . . . ?
C10 C2 C3 C12 -6.4(3) . . . . ?
C2 C3 C4 C5 0.3(3) . . . . ?
C12 C3 C4 C5 -177.7(2) . . . . ?
C2 C3 C4 C15 -177.9(2) . . . . ?
C12 C3 C4 C15 4.1(3) . . . . ?
C3 C4 C5 C6 1.7(3) . . . . ?
C15 C4 C5 C6 179.9(2) . . . . ?
C3 C4 C5 C17 179.2(2) . . . . ?
C15 C4 C5 C17 -2.6(3) . . . . ?
C2 C1 C6 C5 0.2(3) . . . . ?
C7 C1 C6 C5 179.5(2) . . . . ?
C2 C1 C6 C20 177.3(2) . . . . ?
C7 C1 C6 C20 -3.3(3) . . . . ?
C4 C5 C6 C1 -1.9(3) . . . . ?
C17 C5 C6 C1 -179.3(2) . . . . ?
C4 C5 C6 C20 -179.1(2) . . . . ?
C17 C5 C6 C20 3.5(3) . . . . ?
C8 N1 C7 C1 171.4(2) . . . . ?
C6 C1 C7 N1 99.1(3) . . . . ?
C2 C1 C7 N1 -81.5(3) . . . . ?
C7 N1 C8 O1 0.3(4) . . . . ?
C7 N1 C8 C9 -179.7(3) . . . . ?
C3 C2 C10 C11 -82.1(3) . . . . ?
C1 C2 C10 C11 95.5(3) . . . . ?
C13 N2 C12 C3 -126.6(2) . . . . ?
C4 C3 C12 N2 81.3(3) . . . . ?
C2 C3 C12 N2 -96.6(2) . . . . ?
C12 N2 C13 O2 -3.7(4) . . . . ?
C12 N2 C13 C14 177.2(2) . . . . ?
C3 C4 C15 C16 88.1(3) . . . . ?
C5 C4 C15 C16 -90.1(3) . . . . ?
C18 N3 C17 C5 145.5(3) . . . . ?
C4 C5 C17 N3 -81.2(3) . . . . ?
C6 C5 C17 N3 96.3(3) . . . . ?
C17 N3 C18 O3 -0.4(4) . . . . ?
C17 N3 C18 C19 -179.9(2) . . . . ?
C1 C6 C20 C21 -85.7(3) . . . . ?
C5 C6 C20 C21 91.4(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O1 H1O O3 1.03 1.43 2.452(2) 168.5 2 yes
N1 H1N O2 0.83(3) 1.90(3) 2.712(3) 164(3) 4_565 yes
N2 H2N Br4 0.80(3) 2.70(3) 3.492(2) 174(3) 3_666 yes
N3 H3N Br4 0.82(3) 2.73(3) 3.530(2) 165(3) . yes

_refine_diff_density_max         1.536
_refine_diff_density_min         -1.161
_refine_diff_density_rms         0.109



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichloromethane / methanol / diethyl ether'
