# Electronic Supplementary Material (ESI) for Materials Chemistry Frontiers.
# This journal is © the Partner Organisations 2023

####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 2239763'
loop_
_audit_author_name
_audit_author_address
'YingFeng Han'
;Northwest univeristy
China
;
_audit_update_record             
;
2023-02-03 deposited with the CCDC.	2023-04-04 downloaded from the CCDC.
;
_audit_creation_date             2022-10-11
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H20 Au Br N4 O4'
_chemical_formula_sum            'C15 H20 Au Br N4 O4'
_chemical_formula_weight         597.23
_chemical_melting_point          ?
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'
Br Br -0.2901 2.4595 '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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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                   14.3250(7)
_cell_length_b                   8.8390(4)
_cell_length_c                   14.6957(8)
_cell_angle_alpha                90
_cell_angle_beta                 93.103(2)
_cell_angle_gamma                90
_cell_volume                     1858.02(16)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9447
_cell_measurement_temperature    228(2)
_cell_measurement_theta_max      26.37
_cell_measurement_theta_min      2.69
_shelx_estimated_absorpt_T_max   0.171
_shelx_estimated_absorpt_T_min   0.152
_exptl_absorpt_coefficient_mu    10.095
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.4035
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1268 before and 0.0513 after correction.
The Ratio of minimum to maximum transmission is 0.5413.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.135
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1136
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.27
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0293
_diffrn_reflns_av_unetI/netI     0.0323
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            12793
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.392
_diffrn_reflns_theta_min         2.690
_diffrn_ambient_temperature      228.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3366
_reflns_number_total             3804
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.902
_refine_diff_density_min         -0.635
_refine_diff_density_rms         0.114
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.132
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         3804
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0334
_refine_ls_R_factor_gt           0.0273
_refine_ls_restrained_S_all      1.132
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0142P)²+4.5419P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0573
_refine_ls_wR_factor_ref         0.0591
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C9(H9A,H9B), C10(H10A,H10B), C11(H11A,H11B), C12(H12A,H12B),
 C13(H13A,H13B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C7(H7)
2.c Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C15(H15A,H15B,H15C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
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 0.37274(2) 0.82157(2) 0.88152(2) 0.03147(7) Uani 1 1 d . . . . .
Br1 Br 0.31346(4) 0.86691(6) 1.03433(4) 0.04218(14) Uani 1 1 d . . . . .
N1 N 0.4971(3) 0.8350(4) 0.7223(3) 0.0278(8) Uani 1 1 d . . . . .
O1 O 0.4002(3) 0.5142(4) 0.3535(3) 0.0528(10) Uani 1 1 d . . . . .
O2 O 0.6232(3) 0.6741(4) 0.3624(3) 0.0468(9) Uani 1 1 d . . . . .
N2 N 0.3668(3) 0.7167(4) 0.6881(3) 0.0258(8) Uani 1 1 d . . . . .
O3 O 0.4362(3) 0.7377(5) 0.3059(3) 0.0504(10) Uani 1 1 d . . . . .
N3 N 0.4301(3) 0.6419(5) 0.3652(3) 0.0349(10) Uani 1 1 d . . . . .
O4 O 0.6485(3) 0.9068(5) 0.4050(3) 0.0566(11) Uani 1 1 d . . . . .
N4 N 0.6083(3) 0.7850(5) 0.4095(3) 0.0375(10) Uani 1 1 d . . . . .
C1 C 0.4150(3) 0.7186(5) 0.6098(3) 0.0253(10) Uani 1 1 d . . . . .
C2 C 0.4984(3) 0.7965(5) 0.6305(3) 0.0298(10) Uani 1 1 d . . . . .
C3 C 0.3927(3) 0.6617(5) 0.5240(3) 0.0293(10) Uani 1 1 d . . . . .
H3 H 0.337071 0.608002 0.510402 0.035 Uiso 1 1 calc R . . . .
C4 C 0.4568(3) 0.6884(5) 0.4595(3) 0.0300(10) Uani 1 1 d . . . . .
C5 C 0.4163(3) 0.7880(5) 0.7576(3) 0.0309(11) Uani 1 1 d . . . . .
C6 C 0.5395(3) 0.7679(5) 0.4789(3) 0.0312(11) Uani 1 1 d . . . . .
C7 C 0.5629(3) 0.8219(5) 0.5654(3) 0.0325(11) Uani 1 1 d . . . . .
H7 H 0.619404 0.873014 0.579220 0.039 Uiso 1 1 calc R . . . .
C8 C 0.6568(3) 0.8053(5) 0.7945(4) 0.0348(11) Uani 1 1 d . . . . .
H8A H 0.674422 0.757086 0.737902 0.042 Uiso 1 1 calc R . . . .
H8B H 0.710363 0.865114 0.818289 0.042 Uiso 1 1 calc R . . . .
C9 C 0.5745(3) 0.9111(5) 0.7732(4) 0.0346(11) Uani 1 1 d . . . . .
H9A H 0.552106 0.950639 0.830444 0.041 Uiso 1 1 calc R . . . .
H9B H 0.595501 0.997043 0.737546 0.041 Uiso 1 1 calc R . . . .
C10 C 0.1021(3) 0.7438(6) 0.6404(4) 0.0357(12) Uani 1 1 d . . . . .
H10A H 0.095010 0.668056 0.591757 0.043 Uiso 1 1 calc R . . . .
H10B H 0.083024 0.697301 0.696968 0.043 Uiso 1 1 calc R . . . .
C11 C 0.2038(3) 0.7917(5) 0.6518(3) 0.0312(11) Uani 1 1 d . . . . .
H11A H 0.225229 0.822620 0.592396 0.037 Uiso 1 1 calc R . . . .
H11B H 0.208513 0.879941 0.692237 0.037 Uiso 1 1 calc R . . . .
C12 C 0.2680(3) 0.6687(5) 0.6906(3) 0.0279(10) Uani 1 1 d . . . . .
H12A H 0.253129 0.647357 0.753693 0.034 Uiso 1 1 calc R . . . .
H12B H 0.258239 0.575662 0.655078 0.034 Uiso 1 1 calc R . . . .
C13 C 0.6360(4) 0.6839(6) 0.8629(4) 0.0440(13) Uani 1 1 d . . . . .
H13A H 0.621049 0.732228 0.920374 0.053 Uiso 1 1 calc R . . . .
H13B H 0.580665 0.627188 0.840380 0.053 Uiso 1 1 calc R . . . .
C14 C 0.7158(4) 0.5744(6) 0.8814(4) 0.0510(15) Uani 1 1 d . . . . .
H14A H 0.734938 0.532955 0.824185 0.077 Uiso 1 1 calc GR . . . .
H14B H 0.695558 0.492935 0.919930 0.077 Uiso 1 1 calc GR . . . .
H14C H 0.768033 0.626977 0.911852 0.077 Uiso 1 1 calc GR . . . .
C15 C 0.0396(4) 0.8782(7) 0.6169(5) 0.0558(17) Uani 1 1 d . . . . .
H15A H 0.058318 0.923977 0.560737 0.084 Uiso 1 1 calc GR . . . .
H15B H 0.045347 0.951969 0.665765 0.084 Uiso 1 1 calc GR . . . .
H15C H -0.024806 0.844675 0.609235 0.084 Uiso 1 1 calc GR . . . .


_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 2.4761(6) . ?
Au1 C5 1.980(5) . ?
N1 C2 1.393(6) . ?
N1 C5 1.358(6) . ?
N1 C9 1.467(6) . ?
O1 N3 1.216(5) . ?
O2 N4 1.225(6) . ?
N2 C1 1.374(6) . ?
N2 C5 1.365(6) . ?
N2 C12 1.480(5) . ?
O3 N3 1.221(5) . ?
N3 C4 1.476(6) . ?
O4 N4 1.224(6) . ?
N4 C6 1.464(6) . ?
C1 C2 1.397(6) . ?
C1 C3 1.379(7) . ?
C2 C7 1.384(7) . ?
C3 H3 0.9400 . ?
C3 C4 1.375(7) . ?
C4 C6 1.394(7) . ?
C6 C7 1.381(7) . ?
C7 H7 0.9400 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 C9 1.524(7) . ?
C8 C13 1.512(7) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 C11 1.518(6) . ?
C10 C15 1.516(7) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 C12 1.515(6) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 C14 1.511(7) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 H14C 0.9700 . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 H15C 0.9700 . ?

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
C5 Au1 Br1 178.14(13) . . ?
C2 N1 C9 123.8(4) . . ?
C5 N1 C2 110.6(4) . . ?
C5 N1 C9 125.6(4) . . ?
C1 N2 C12 123.3(4) . . ?
C5 N2 C1 110.8(4) . . ?
C5 N2 C12 124.9(4) . . ?
O1 N3 O3 125.6(5) . . ?
O1 N3 C4 117.5(4) . . ?
O3 N3 C4 116.9(4) . . ?
O2 N4 C6 117.1(4) . . ?
O4 N4 O2 125.2(5) . . ?
O4 N4 C6 117.7(5) . . ?
N2 C1 C2 106.7(4) . . ?
N2 C1 C3 131.2(4) . . ?
C3 C1 C2 122.1(5) . . ?
N1 C2 C1 106.0(4) . . ?
C7 C2 N1 132.4(5) . . ?
C7 C2 C1 121.6(5) . . ?
C1 C3 H3 122.0 . . ?
C4 C3 C1 115.9(4) . . ?
C4 C3 H3 122.0 . . ?
C3 C4 N3 116.8(4) . . ?
C3 C4 C6 122.5(5) . . ?
C6 C4 N3 120.4(4) . . ?
N1 C5 Au1 128.5(3) . . ?
N1 C5 N2 106.0(4) . . ?
N2 C5 Au1 125.5(4) . . ?
C4 C6 N4 120.4(5) . . ?
C7 C6 N4 117.8(4) . . ?
C7 C6 C4 121.6(5) . . ?
C2 C7 H7 121.9 . . ?
C6 C7 C2 116.3(5) . . ?
C6 C7 H7 121.9 . . ?
H8A C8 H8B 107.8 . . ?
C9 C8 H8A 108.9 . . ?
C9 C8 H8B 108.9 . . ?
C13 C8 H8A 108.9 . . ?
C13 C8 H8B 108.9 . . ?
C13 C8 C9 113.2(4) . . ?
N1 C9 C8 112.3(4) . . ?
N1 C9 H9A 109.2 . . ?
N1 C9 H9B 109.2 . . ?
C8 C9 H9A 109.2 . . ?
C8 C9 H9B 109.2 . . ?
H9A C9 H9B 107.9 . . ?
H10A C10 H10B 108.0 . . ?
C11 C10 H10A 109.4 . . ?
C11 C10 H10B 109.4 . . ?
C15 C10 H10A 109.4 . . ?
C15 C10 H10B 109.4 . . ?
C15 C10 C11 111.0(4) . . ?
C10 C11 H11A 108.8 . . ?
C10 C11 H11B 108.8 . . ?
H11A C11 H11B 107.7 . . ?
C12 C11 C10 113.6(4) . . ?
C12 C11 H11A 108.8 . . ?
C12 C11 H11B 108.8 . . ?
N2 C12 C11 110.2(4) . . ?
N2 C12 H12A 109.6 . . ?
N2 C12 H12B 109.6 . . ?
C11 C12 H12A 109.6 . . ?
C11 C12 H12B 109.6 . . ?
H12A C12 H12B 108.1 . . ?
C8 C13 H13A 108.9 . . ?
C8 C13 H13B 108.9 . . ?
H13A C13 H13B 107.7 . . ?
C14 C13 C8 113.5(5) . . ?
C14 C13 H13A 108.9 . . ?
C14 C13 H13B 108.9 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C10 C15 H15A 109.5 . . ?
C10 C15 H15B 109.5 . . ?
C10 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 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
N1 C2 C7 C6 -179.1(4) . . . . ?
O1 N3 C4 C3 -49.6(6) . . . . ?
O1 N3 C4 C6 136.2(5) . . . . ?
O2 N4 C6 C4 -41.2(6) . . . . ?
O2 N4 C6 C7 133.6(5) . . . . ?
N2 C1 C2 N1 1.4(5) . . . . ?
N2 C1 C2 C7 -178.6(4) . . . . ?
N2 C1 C3 C4 177.9(4) . . . . ?
O3 N3 C4 C3 127.3(5) . . . . ?
O3 N3 C4 C6 -46.9(6) . . . . ?
N3 C4 C6 N4 -10.0(6) . . . . ?
N3 C4 C6 C7 175.4(4) . . . . ?
O4 N4 C6 C4 141.1(5) . . . . ?
O4 N4 C6 C7 -44.1(6) . . . . ?
N4 C6 C7 C2 -176.6(4) . . . . ?
C1 N2 C5 Au1 177.1(3) . . . . ?
C1 N2 C5 N1 -0.2(5) . . . . ?
C1 N2 C12 C11 -75.8(5) . . . . ?
C1 C2 C7 C6 0.9(7) . . . . ?
C1 C3 C4 N3 -174.1(4) . . . . ?
C1 C3 C4 C6 0.0(7) . . . . ?
C2 N1 C5 Au1 -176.1(3) . . . . ?
C2 N1 C5 N2 1.1(5) . . . . ?
C2 N1 C9 C8 -73.9(6) . . . . ?
C2 C1 C3 C4 -1.0(6) . . . . ?
C3 C1 C2 N1 -179.5(4) . . . . ?
C3 C1 C2 C7 0.6(7) . . . . ?
C3 C4 C6 N4 176.1(4) . . . . ?
C3 C4 C6 C7 1.5(7) . . . . ?
C4 C6 C7 C2 -1.9(7) . . . . ?
C5 N1 C2 C1 -1.6(5) . . . . ?
C5 N1 C2 C7 178.4(5) . . . . ?
C5 N1 C9 C8 103.8(5) . . . . ?
C5 N2 C1 C2 -0.7(5) . . . . ?
C5 N2 C1 C3 -179.8(4) . . . . ?
C5 N2 C12 C11 92.3(5) . . . . ?
C9 N1 C2 C1 176.5(4) . . . . ?
C9 N1 C2 C7 -3.6(8) . . . . ?
C9 N1 C5 Au1 5.9(6) . . . . ?
C9 N1 C5 N2 -176.9(4) . . . . ?
C9 C8 C13 C14 177.5(5) . . . . ?
C10 C11 C12 N2 172.4(4) . . . . ?
C12 N2 C1 C2 168.9(4) . . . . ?
C12 N2 C1 C3 -10.2(7) . . . . ?
C12 N2 C5 Au1 7.7(6) . . . . ?
C12 N2 C5 N1 -169.6(4) . . . . ?
C13 C8 C9 N1 -68.9(6) . . . . ?
C15 C10 C11 C12 170.3(5) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_4
_database_code_depnum_ccdc_archive 'CCDC 2239765'
loop_
_audit_author_name
_audit_author_address
'YingFeng Han'
;Northwest univeristy
China
;
_audit_update_record             
;
2023-02-03 deposited with the CCDC.	2023-04-04 downloaded from the CCDC.
;
_audit_creation_date             2022-10-15
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C25 H22 Au Br N2, C H2 Cl2'
_chemical_formula_sum            'C26 H24 Au Br Cl2 N2'
_chemical_formula_weight         712.25
_chemical_melting_point          ?
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'
Br Br -0.2901 2.4595 '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'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.3079(5)
_cell_length_b                   11.3455(6)
_cell_length_c                   12.2406(7)
_cell_angle_alpha                111.256(2)
_cell_angle_beta                 104.585(2)
_cell_angle_gamma                90.394(2)
_cell_volume                     1283.47(12)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9934
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      25.51
_cell_measurement_theta_min      2.36
_shelx_estimated_absorpt_T_max   0.245
_shelx_estimated_absorpt_T_min   0.212
_exptl_absorpt_coefficient_mu    7.512
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_correction_T_min  0.5427
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1182 before and 0.0629 after correction.
The Ratio of minimum to maximum transmission is 0.7282.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.843
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             684
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.26
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0412
_diffrn_reflns_av_unetI/netI     0.0400
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            19305
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.636
_diffrn_reflns_theta_min         2.363
_diffrn_ambient_temperature      200.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4255
_reflns_number_total             4821
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         1.175
_refine_diff_density_min         -1.193
_refine_diff_density_rms         0.117
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     290
_refine_ls_number_reflns         4821
_refine_ls_number_restraints     13
_refine_ls_R_factor_all          0.0378
_refine_ls_R_factor_gt           0.0309
_refine_ls_restrained_S_all      1.074
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0279P)²+2.7720P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0689
_refine_ls_wR_factor_ref         0.0723
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(Cl1) \\sim Ueq: with sigma of 0.001 and sigma for terminal atoms of 0.01
3. Rigid body (RIGU) restrains
 C26, Cl2, Cl1
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
4.a Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B), C23(H23A,H23B), C25(H25A,H25B), C26(H26A,H26B)
4.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C9(H9), C10(H10), C11(H11), C14(H14), C15(H15), C17(H17),
 C18(H18), C19(H19), C20(H20), C21(H21), C22(H22)
4.c Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
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 0.36222(2) 0.87296(2) 0.48224(2) 0.03647(8) Uani 1 1 d . . . . .
Br1 Br 0.30530(6) 0.89880(6) 0.66679(5) 0.04853(15) Uani 1 1 d . . . . .
N1 N 0.3652(4) 0.9064(4) 0.2498(4) 0.0357(9) Uani 1 1 d . . . . .
N2 N 0.4817(4) 0.7558(4) 0.2748(4) 0.0329(9) Uani 1 1 d . . . . .
C1 C 0.4153(5) 0.8561(5) 0.1490(5) 0.0377(12) Uani 1 1 d . . . . .
C2 C 0.4896(5) 0.7588(5) 0.1642(4) 0.0344(11) Uani 1 1 d . . . . .
C3 C 0.5557(5) 0.6880(5) 0.0800(5) 0.0429(12) Uani 1 1 d . . . . .
H3 H 0.606049 0.621274 0.090831 0.051 Uiso 1 1 calc R . . . .
C4 C 0.4053(6) 0.8866(5) 0.0464(5) 0.0465(13) Uani 1 1 d . . . . .
H4 H 0.355419 0.953285 0.034994 0.056 Uiso 1 1 calc R . . . .
C5 C 0.4514(5) 0.5572(5) 0.3044(4) 0.0353(11) Uani 1 1 d . . . . .
C6 C 0.4070(5) 0.8461(5) 0.3271(5) 0.0358(11) Uani 1 1 d . . . . .
C7 C 0.5373(5) 0.6625(4) 0.3231(4) 0.0318(10) Uani 1 1 d . . . . .
C8 C 0.6748(5) 0.6791(5) 0.3823(4) 0.0336(11) Uani 1 1 d . . . . .
C9 C 0.4695(6) 0.8171(6) -0.0365(5) 0.0526(15) Uani 1 1 d . . . . .
H9 H 0.463454 0.835286 -0.107473 0.063 Uiso 1 1 calc R . . . .
C10 C 0.5442(6) 0.7199(6) -0.0196(5) 0.0506(14) Uani 1 1 d . . . . .
H10 H 0.588452 0.674296 -0.079011 0.061 Uiso 1 1 calc R . . . .
C11 C 0.3102(5) 0.5393(5) 0.2433(5) 0.0435(13) Uani 1 1 d . . . . .
H11 H 0.271058 0.601107 0.213458 0.052 Uiso 1 1 calc R . . . .
C12 C 0.7278(5) 0.5851(5) 0.4276(4) 0.0367(11) Uani 1 1 d . . . . .
C13 C 0.5079(5) 0.4625(5) 0.3482(4) 0.0354(11) Uani 1 1 d . . . . .
C14 C 0.7638(5) 0.7859(5) 0.3988(5) 0.0433(13) Uani 1 1 d . . . . .
H14 H 0.730170 0.848728 0.367910 0.052 Uiso 1 1 calc R . . . .
C15 C 0.4202(5) 0.3542(5) 0.3286(5) 0.0423(12) Uani 1 1 d . . . . .
H15 H 0.455836 0.290013 0.356463 0.051 Uiso 1 1 calc R . . . .
C16 C 0.2831(6) 1.0128(5) 0.2716(6) 0.0504(14) Uani 1 1 d . . . . .
H16A H 0.323320 1.080939 0.253748 0.060 Uiso 1 1 calc R . . . .
H16B H 0.284867 1.047742 0.358812 0.060 Uiso 1 1 calc R . . . .
C17 C 0.2324(6) 0.4350(6) 0.2279(6) 0.0512(14) Uani 1 1 d . . . . .
H17 H 0.138937 0.424407 0.187392 0.061 Uiso 1 1 calc R . . . .
C18 C 0.6433(5) 0.4791(5) 0.4084(5) 0.0393(12) Uani 1 1 d . . . . .
H18 H 0.680069 0.416190 0.437674 0.047 Uiso 1 1 calc R . . . .
C19 C 0.8972(6) 0.7967(6) 0.4591(6) 0.0532(15) Uani 1 1 d . . . . .
H19 H 0.956227 0.866578 0.468574 0.064 Uiso 1 1 calc R . . . .
C20 C 0.2878(6) 0.3418(5) 0.2711(5) 0.0482(14) Uani 1 1 d . . . . .
H20 H 0.231243 0.269436 0.259676 0.058 Uiso 1 1 calc R . . . .
C21 C 0.8666(6) 0.6039(6) 0.4920(5) 0.0515(14) Uani 1 1 d . . . . .
H21 H 0.902786 0.543331 0.524917 0.062 Uiso 1 1 calc R . . . .
C22 C 0.9486(6) 0.7056(6) 0.5076(5) 0.0522(15) Uani 1 1 d . . . . .
H22 H 1.040959 0.715791 0.551305 0.063 Uiso 1 1 calc R . . . .
C23 C 0.1381(7) 0.9755(8) 0.1949(9) 0.087(3) Uani 1 1 d . . . . .
H23A H 0.090716 1.052989 0.213002 0.105 Uiso 1 1 calc R . . . .
H23B H 0.138030 0.946707 0.108266 0.105 Uiso 1 1 calc R . . . .
C24 C -0.0880(8) 0.8558(11) 0.1238(10) 0.137(5) Uani 1 1 d . . . . .
H24A H -0.087368 0.821526 0.038043 0.205 Uiso 1 1 calc GR . . . .
H24B H -0.129208 0.935777 0.141437 0.205 Uiso 1 1 calc GR . . . .
H24C H -0.140148 0.794356 0.139834 0.205 Uiso 1 1 calc GR . . . .
C25 C 0.0618(8) 0.8811(9) 0.2079(10) 0.113(3) Uani 1 1 d . . . . .
H25A H 0.060425 0.907698 0.294026 0.135 Uiso 1 1 calc R . . . .
H25B H 0.104992 0.801188 0.186431 0.135 Uiso 1 1 calc R . . . .
Cl1 Cl 0.1053(2) 0.7101(4) -0.1849(3) 0.1421(12) Uani 1 1 d . U . . .
Cl2 Cl 0.1416(3) 0.5428(4) -0.0550(3) 0.1431(12) Uani 1 1 d . U . . .
C26 C 0.1810(9) 0.5788(10) -0.1568(8) 0.098(3) Uani 1 1 d . U . . .
H26A H 0.155877 0.503282 -0.233930 0.118 Uiso 1 1 calc R . . . .
H26B H 0.280155 0.598462 -0.133248 0.118 Uiso 1 1 calc R . . . .


_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 2.3922(6) . ?
Au1 C6 1.983(5) . ?
N1 C1 1.389(7) . ?
N1 C6 1.349(6) . ?
N1 C16 1.463(7) . ?
N2 C2 1.389(6) . ?
N2 C6 1.355(6) . ?
N2 C7 1.446(6) . ?
C1 C2 1.389(7) . ?
C1 C4 1.398(7) . ?
C2 C3 1.391(7) . ?
C3 H3 0.9500 . ?
C3 C10 1.370(8) . ?
C4 H4 0.9500 . ?
C4 C9 1.363(8) . ?
C5 C7 1.396(7) . ?
C5 C11 1.435(7) . ?
C5 C13 1.432(7) . ?
C7 C8 1.396(7) . ?
C8 C12 1.424(7) . ?
C8 C14 1.437(7) . ?
C9 H9 0.9500 . ?
C9 C10 1.397(9) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C11 C17 1.352(8) . ?
C12 C18 1.391(7) . ?
C12 C21 1.421(7) . ?
C13 C15 1.430(7) . ?
C13 C18 1.380(7) . ?
C14 H14 0.9500 . ?
C14 C19 1.369(8) . ?
C15 H15 0.9500 . ?
C15 C20 1.349(8) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 C23 1.514(9) . ?
C17 H17 0.9500 . ?
C17 C20 1.409(8) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C19 C22 1.413(8) . ?
C20 H20 0.9500 . ?
C21 H21 0.9500 . ?
C21 C22 1.352(8) . ?
C22 H22 0.9500 . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C23 C25 1.401(11) . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C24 C25 1.583(12) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
Cl1 C26 1.789(10) . ?
Cl2 C26 1.582(9) . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?

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
C6 Au1 Br1 178.25(14) . . ?
C1 N1 C16 125.0(4) . . ?
C6 N1 C1 110.4(4) . . ?
C6 N1 C16 124.6(4) . . ?
C2 N2 C7 124.3(4) . . ?
C6 N2 C2 111.1(4) . . ?
C6 N2 C7 124.4(4) . . ?
N1 C1 C2 106.9(4) . . ?
N1 C1 C4 132.9(5) . . ?
C2 C1 C4 120.2(5) . . ?
N2 C2 C3 132.2(5) . . ?
C1 C2 N2 105.4(4) . . ?
C1 C2 C3 122.4(5) . . ?
C2 C3 H3 121.9 . . ?
C10 C3 C2 116.2(5) . . ?
C10 C3 H3 121.9 . . ?
C1 C4 H4 121.2 . . ?
C9 C4 C1 117.6(5) . . ?
C9 C4 H4 121.2 . . ?
C7 C5 C11 123.3(5) . . ?
C7 C5 C13 118.0(4) . . ?
C13 C5 C11 118.7(5) . . ?
N1 C6 Au1 128.3(4) . . ?
N1 C6 N2 106.2(4) . . ?
N2 C6 Au1 125.4(4) . . ?
C5 C7 N2 118.2(4) . . ?
C5 C7 C8 123.0(4) . . ?
C8 C7 N2 118.8(4) . . ?
C7 C8 C12 117.9(4) . . ?
C7 C8 C14 122.9(5) . . ?
C12 C8 C14 119.2(5) . . ?
C4 C9 H9 119.3 . . ?
C4 C9 C10 121.4(5) . . ?
C10 C9 H9 119.3 . . ?
C3 C10 C9 122.2(6) . . ?
C3 C10 H10 118.9 . . ?
C9 C10 H10 118.9 . . ?
C5 C11 H11 119.8 . . ?
C17 C11 C5 120.4(5) . . ?
C17 C11 H11 119.8 . . ?
C18 C12 C8 119.6(5) . . ?
C18 C12 C21 122.3(5) . . ?
C21 C12 C8 118.1(5) . . ?
C15 C13 C5 118.2(5) . . ?
C18 C13 C5 119.3(5) . . ?
C18 C13 C15 122.5(5) . . ?
C8 C14 H14 120.2 . . ?
C19 C14 C8 119.6(5) . . ?
C19 C14 H14 120.2 . . ?
C13 C15 H15 119.5 . . ?
C20 C15 C13 121.0(5) . . ?
C20 C15 H15 119.5 . . ?
N1 C16 H16A 109.0 . . ?
N1 C16 H16B 109.0 . . ?
N1 C16 C23 113.0(5) . . ?
H16A C16 H16B 107.8 . . ?
C23 C16 H16A 109.0 . . ?
C23 C16 H16B 109.0 . . ?
C11 C17 H17 119.5 . . ?
C11 C17 C20 121.0(5) . . ?
C20 C17 H17 119.5 . . ?
C12 C18 H18 118.9 . . ?
C13 C18 C12 122.2(5) . . ?
C13 C18 H18 118.9 . . ?
C14 C19 H19 119.5 . . ?
C14 C19 C22 121.0(5) . . ?
C22 C19 H19 119.5 . . ?
C15 C20 C17 120.8(5) . . ?
C15 C20 H20 119.6 . . ?
C17 C20 H20 119.6 . . ?
C12 C21 H21 119.1 . . ?
C22 C21 C12 121.8(5) . . ?
C22 C21 H21 119.1 . . ?
C19 C22 H22 119.9 . . ?
C21 C22 C19 120.1(5) . . ?
C21 C22 H22 119.9 . . ?
C16 C23 H23A 107.8 . . ?
C16 C23 H23B 107.8 . . ?
H23A C23 H23B 107.1 . . ?
C25 C23 C16 118.1(8) . . ?
C25 C23 H23A 107.8 . . ?
C25 C23 H23B 107.8 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C25 C24 H24A 109.5 . . ?
C25 C24 H24B 109.5 . . ?
C25 C24 H24C 109.5 . . ?
C23 C25 C24 111.7(9) . . ?
C23 C25 H25A 109.3 . . ?
C23 C25 H25B 109.3 . . ?
C24 C25 H25A 109.3 . . ?
C24 C25 H25B 109.3 . . ?
H25A C25 H25B 107.9 . . ?
Cl1 C26 H26A 108.3 . . ?
Cl1 C26 H26B 108.3 . . ?
Cl2 C26 Cl1 115.8(6) . . ?
Cl2 C26 H26A 108.3 . . ?
Cl2 C26 H26B 108.3 . . ?
H26A C26 H26B 107.4 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_3
_database_code_depnum_ccdc_archive 'CCDC 2239764'
loop_
_audit_author_name
_audit_author_address
'YingFeng Han'
;Northwest univeristy
China
;
_audit_update_record             
;
2023-02-03 deposited with the CCDC.	2023-04-04 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT342_3                   
;
PROBLEM: Low Bond Precision on  C-C Bonds     0.0375 Ang.  
RESPONSE: The low bond precision arises from the mobile of nBu group. 
;
# end Validation Reply Form

_audit_creation_date             2022-06-22
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H26 Au Br N2'
_chemical_formula_sum            'C17 H26 Au Br N2'
_chemical_formula_weight         535.27
_chemical_melting_point          ?
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'
Br Br -0.2901 2.4595 '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'

_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.
;
_space_group_crystal_system      tetragonal
_space_group_IT_number           86
_space_group_name_H-M_alt        'P 42/n'
_space_group_name_Hall           '-P 4bc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z'
'-y, x+1/2, z+1/2'
'y+1/2, -x, z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z'
'y, -x-1/2, -z-1/2'
'-y-1/2, x, -z-1/2'

_cell_length_a                   12.1551(9)
_cell_length_b                   12.1551(9)
_cell_length_c                   28.806(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4255.9(7)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9831
_cell_measurement_temperature    222(2)
_cell_measurement_theta_max      24.53
_cell_measurement_theta_min      2.37
_shelx_estimated_absorpt_T_max   0.301
_shelx_estimated_absorpt_T_min   0.237
_exptl_absorpt_coefficient_mu    8.788
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_correction_T_min  0.4811
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1046 before and 0.0668 after correction.
The Ratio of minimum to maximum transmission is 0.6455.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.671
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             2048
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.18
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0889
_diffrn_reflns_av_unetI/netI     0.0508
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            41503
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.047
_diffrn_reflns_theta_min         1.818
_diffrn_ambient_temperature      222.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2820
_reflns_number_total             4138
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         3.140
_refine_diff_density_min         -2.127
_refine_diff_density_rms         0.323
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.100
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     203
_refine_ls_number_reflns         4138
_refine_ls_number_restraints     269
_refine_ls_R_factor_all          0.1805
_refine_ls_R_factor_gt           0.1478
_refine_ls_restrained_S_all      1.066
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0640P)²+399.3654P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3342
_refine_ls_wR_factor_ref         0.3510
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C15-C2 = C12-C8
 1.47 with sigma of 0.01
 C17-C18 = C19-C16 = C18-C14 = C16-C14 = C14-C9 = C11-C1 = C10-C1 = C13-C10
 1.54 with sigma of 0.01
 N1-C5 \\sim N2-C5
 with sigma of 0.02
 N1-C4 \\sim N2-C6
 with sigma of 0.02
3. Restrained planarity
 C2, C8, C12, C7, C6, C4, C3, C5, N1, N2
 with sigma of 0.01
4. Uiso/Uaniso restraints and constraints
Uanis(C9) \\sim Ueq, Uanis(C14) \\sim Ueq, Uanis(N1) \\sim Ueq, Uanis(C16)
\\sim Ueq, Uanis(C6) \\sim Ueq, Uanis(C5) \\sim Ueq, Uanis(N2) \\sim Ueq,
Uanis(C8) \\sim Ueq, Uanis(C12) \\sim Ueq, Uanis(C2) \\sim Ueq, Uanis(C15)
\\sim Ueq, Uanis(C3) \\sim Ueq: with sigma of 0.001 and sigma for terminal
atoms of 0.002
Uanis(C18) \\sim Ueq, Uanis(C17) \\sim Ueq, Uanis(C19) \\sim Ueq, Uanis(C16)
\\sim Ueq: with sigma of 0.001 and sigma for terminal atoms of 0.002
5. Rigid body (RIGU) restrains
 C12, C8, C2, C15, C3, C4, C6, C7, N2, C11, C1, C10, C13, C5, N1, Au1, Br1, C9,
  C14, C16
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
 C14, C18, C17, C19, C16
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
6. Others
 Fixed Sof: H14C(0.5) H14D(0.5) H14A(0.5) H14B(0.5) C16(0.5) H16A(0.5)
 H16B(0.5) C17(0.5) H17A(0.5) H17B(0.5) H17C(0.5) C18(0.5) H18A(0.5) H18B(0.5)
 C19(0.5) H19A(0.5) H19B(0.5) H19C(0.5)
7.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C9(H9A,H9B), C10(H10A,H10B), C11(H11A,H11B), C14(H14C,H14D),
 C14(H14A,H14B), C16(H16A,H16B), C18(H18A,H18B)
7.b Me refined with riding coordinates:
 C17(H17A,H17B,H17C)
7.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C7(H7)
7.d Fitted pentagon refined as free rotating group:
 C4(N1,C5,N2,C6)
7.e Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C13(H13A,H13B,H13C), C15(H15A,H15B,H15C), C19(H19A,H19B,
 H19C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
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 -0.02317(10) 0.51109(12) 0.66140(4) 0.0690(5) Uani 1 1 d . U . . .
Br1 Br -0.2052(3) 0.4444(5) 0.66032(16) 0.1045(15) Uani 1 1 d . U . . .
C1 C 0.197(2) 0.4864(18) 0.7706(8) 0.052(5) Uani 1 1 d D U . . .
H1A H 0.169436 0.421338 0.754084 0.063 Uiso 1 1 calc R . . . .
H1B H 0.277222 0.484115 0.770038 0.063 Uiso 1 1 calc R . . . .
C2 C 0.493(2) 0.6619(14) 0.6320(10) 0.064(3) Uani 1 1 d D U . . .
C3 C 0.393(3) 0.6308(17) 0.6062(11) 0.064(3) Uani 1 1 d . U . . .
H3 H 0.391624 0.626151 0.573675 0.077 Uiso 1 1 calc R . . . .
C4 C 0.2999(13) 0.6088(10) 0.6328(6) 0.060(5) Uani 1 1 d D U . . .
N1 N 0.1915(15) 0.5772(13) 0.6201(5) 0.064(3) Uani 1 1 d DG U . . .
C5 C 0.1288(11) 0.5654(13) 0.6614(7) 0.062(3) Uani 1 1 d DG U . . .
N2 N 0.1984(15) 0.5897(14) 0.6996(5) 0.061(3) Uani 1 1 d DG U . . .
C6 C 0.3041(12) 0.6165(9) 0.6820(6) 0.061(3) Uani 1 1 d DG U . . .
C7 C 0.397(2) 0.6454(12) 0.7062(10) 0.052(4) Uani 1 1 d . U . . .
H7 H 0.398190 0.650093 0.738780 0.063 Uiso 1 1 calc R . . . .
C8 C 0.489(2) 0.6670(9) 0.6796(10) 0.063(3) Uani 1 1 d D U . . .
C9 C 0.162(3) 0.546(2) 0.5728(11) 0.066(3) Uani 1 1 d D U . . .
H9A H 0.205873 0.591078 0.551578 0.079 Uiso 1 1 calc R . . . .
H9B H 0.084944 0.565084 0.567978 0.079 Uiso 1 1 calc R . . . .
C10 C 0.157(3) 0.482(3) 0.8212(9) 0.079(9) Uani 1 1 d D U . . .
H10A H 0.078160 0.499963 0.821233 0.094 Uiso 1 1 calc R . . . .
H10B H 0.194263 0.541642 0.838056 0.094 Uiso 1 1 calc R . . . .
C11 C 0.157(2) 0.5907(19) 0.7450(10) 0.056(5) Uani 1 1 d D U . . .
H11A H 0.076528 0.592585 0.744369 0.067 Uiso 1 1 calc R . . . .
H11B H 0.183204 0.656414 0.761395 0.067 Uiso 1 1 calc R . . . .
C12 C 0.588(2) 0.6978(13) 0.7058(10) 0.062(4) Uani 1 1 d D U . . .
H12A H 0.617289 0.633404 0.721431 0.094 Uiso 1 1 calc GR . . . .
H12B H 0.569229 0.753298 0.728713 0.094 Uiso 1 1 calc GR . . . .
H12C H 0.642888 0.727008 0.684728 0.094 Uiso 1 1 calc GR . . . .
C13 C 0.172(4) 0.376(3) 0.8492(14) 0.101(13) Uani 1 1 d D U . . .
H13A H 0.186658 0.315233 0.828075 0.151 Uiso 1 1 calc GR . . . .
H13B H 0.106183 0.360649 0.866848 0.151 Uiso 1 1 calc GR . . . .
H13C H 0.234101 0.384219 0.870213 0.151 Uiso 1 1 calc GR . . . .
C14 C 0.177(3) 0.425(2) 0.5579(10) 0.068(3) Uani 1 1 d D U . . .
H14C H 0.254457 0.404316 0.561984 0.082 Uiso 0.5 1 calc R . P A 2
H14D H 0.133511 0.378035 0.578799 0.082 Uiso 0.5 1 calc R . P A 2
H14A H 0.113883 0.399521 0.539555 0.082 Uiso 0.5 1 calc R . P B 1
H14B H 0.184842 0.376645 0.585091 0.082 Uiso 0.5 1 calc R . P B 1
C15 C 0.585(2) 0.694(3) 0.6015(10) 0.067(4) Uani 1 1 d D U . . .
H15A H 0.561759 0.687518 0.569382 0.100 Uiso 1 1 calc GR . . . .
H15B H 0.646779 0.645623 0.607121 0.100 Uiso 1 1 calc GR . . . .
H15C H 0.605503 0.769210 0.608045 0.100 Uiso 1 1 calc GR . . . .
C16 C 0.143(4) 0.398(6) 0.5076(12) 0.068(4) Uani 0.5 1 d D U P C 2
H16A H 0.105239 0.461570 0.493829 0.082 Uiso 0.5 1 calc R . P C 2
H16B H 0.093842 0.334889 0.506853 0.082 Uiso 0.5 1 calc R . P C 2
C17 C 0.330(5) 0.445(6) 0.4796(16) 0.070(5) Uani 0.5 1 d D U P C 1
H17A H 0.408391 0.431342 0.479693 0.104 Uiso 0.5 1 calc R . P C 1
H17B H 0.294364 0.396407 0.457526 0.104 Uiso 0.5 1 calc R . P C 1
H17C H 0.316075 0.520931 0.470901 0.104 Uiso 0.5 1 calc R . P C 1
C18 C 0.283(4) 0.424(6) 0.5284(17) 0.069(4) Uani 0.5 1 d D U P C 1
H18A H 0.330987 0.470742 0.547285 0.083 Uiso 0.5 1 calc R . P C 1
H18B H 0.309757 0.348977 0.534206 0.083 Uiso 0.5 1 calc R . P C 1
C19 C 0.250(5) 0.373(6) 0.480(2) 0.069(5) Uani 0.5 1 d D U P C 2
H19A H 0.277350 0.440409 0.466514 0.103 Uiso 0.5 1 calc GR . P C 2
H19B H 0.233828 0.320045 0.456172 0.103 Uiso 0.5 1 calc GR . P C 2
H19C H 0.304382 0.343277 0.501353 0.103 Uiso 0.5 1 calc GR . P C 2


_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 2.357(5) . ?
Au1 C5 1.962(13) . ?
C1 C10 1.537(10) . ?
C1 C11 1.542(10) . ?
C2 C3 1.48(4) . ?
C2 C8 1.37(4) . ?
C2 C15 1.471(10) . ?
C3 C4 1.39(3) . ?
C4 N1 1.4200 . ?
C4 C6 1.4200 . ?
N1 C5 1.4200 . ?
N1 C9 1.46(3) . ?
C5 N2 1.4200 . ?
N2 C6 1.4200 . ?
N2 C11 1.40(3) . ?
C6 C7 1.37(3) . ?
C7 C8 1.38(4) . ?
C8 C12 1.471(10) . ?
C9 C14 1.543(10) . ?
C10 C13 1.538(10) . ?
C14 C16 1.539(10) . ?
C14 C18 1.543(10) . ?
C16 C19 1.541(10) . ?
C17 C18 1.538(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
C5 Au1 Br1 179.1(6) . . ?
C10 C1 C11 112(2) . . ?
C8 C2 C3 119(2) . . ?
C8 C2 C15 128(3) . . ?
C15 C2 C3 113(3) . . ?
C4 C3 C2 116(3) . . ?
C3 C4 N1 131(2) . . ?
C3 C4 C6 121(2) . . ?
N1 C4 C6 108.0 . . ?
C4 N1 C5 108.0 . . ?
C4 N1 C9 122.5(19) . . ?
C5 N1 C9 128.6(19) . . ?
N1 C5 Au1 122.7(12) . . ?
N2 C5 Au1 129.1(12) . . ?
N2 C5 N1 108.0 . . ?
C6 N2 C5 108.0 . . ?
C11 N2 C5 120.8(19) . . ?
C11 N2 C6 131.0(19) . . ?
N2 C6 C4 108.0 . . ?
C7 C6 C4 123.6(19) . . ?
C7 C6 N2 128.4(19) . . ?
C6 C7 C8 116(2) . . ?
C2 C8 C7 125(2) . . ?
C2 C8 C12 120(3) . . ?
C7 C8 C12 115(3) . . ?
N1 C9 C14 119(2) . . ?
C1 C10 C13 119(3) . . ?
N2 C11 C1 109(2) . . ?
C9 C14 C18 105(3) . . ?
C16 C14 C9 115(3) . . ?
C14 C16 C19 107(4) . . ?
C17 C18 C14 144(5) . . ?

_platon_squeeze_details          ?
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.250 0.750 0.449 148 40 ' '
2 -0.250 0.250 0.551 149 40 ' '
3 0.250 0.750 0.949 148 40 ' '
4 0.750 0.250 0.051 149 40 ' '

_platon_squeeze_void_probe_radius 1.20
_olex2_submission_special_instructions 'No special instructions were received'
