# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_HL3PF6
_database_code_depnum_ccdc_archive 'CCDC 1831224'
_audit_update_record             
;
2018-03-20 deposited with the CCDC.
2018-11-22 downloaded from the CCDC.
;

#2015ncs0695

_audit_creation_date             2018-03-16
_audit_creation_method           
;
Olex2 1.2-alpha
(compiled 2018.03.09 svn.r3491 for OlexSys, GUI svn.r5479)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H22 N3 O2, F6 P'
_chemical_formula_sum            'C20 H22 F6 N3 O2 P'
_chemical_formula_weight         481.37
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C20 H22 N3 O2 P F6'
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'
F F 0.0171 0.0103 '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'
P P 0.1023 0.0942 '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                   15.6492(11)
_cell_length_b                   8.2325(6)
_cell_length_c                   16.7492(11)
_cell_angle_alpha                90
_cell_angle_beta                 104.075(7)
_cell_angle_gamma                90
_cell_volume                     2093.1(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4820
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.5810
_cell_measurement_theta_min      2.5890
_shelx_estimated_absorpt_T_max   0.998
_shelx_estimated_absorpt_T_min   0.978
_exptl_absorpt_coefficient_mu    0.208
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.63096
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'CrysAlisPro 1.171.39.34b (Rigaku Oxford Diffraction, 2017) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.528
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             992
_exptl_crystal_recrystallization_method 
'The material was obtained by vapour diffusion of ether into acetone.'
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0679
_diffrn_reflns_av_unetI/netI     0.0699
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            15009
_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         26.023
_diffrn_reflns_theta_min         2.507
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type            'Rigaku HG Saturn724+ (2x2 bin mode)'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -35.00  55.00   1.00   80.00    --  -17.00  72.00  30.00   90
  2  ω    -69.00  22.00   1.00   80.00    --  -17.00 -72.00  90.00   91
  3  ω    -18.00   2.00   1.00   80.00    --  -17.00  54.00-150.00   20
  4  ω    -35.00  73.00   1.00   80.00    --  -17.00  72.00 -60.00  108
  5  ω    -68.00  -7.00   1.00   80.00    --  -17.00 -72.00-180.00   61
;
_diffrn_measurement_device       'four-circle κ goniometer'
_diffrn_measurement_device_type  
'Rigaku FRE+ equipped with VHF Varimax confocal mirrors and an AFC12 goniometer and HG Saturn 724+ detector'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support 'MiTeGen MicroLoop'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0418936000
_diffrn_orient_matrix_UB_12      0.0364210000
_diffrn_orient_matrix_UB_13      0.0040437000
_diffrn_orient_matrix_UB_21      0.0013111000
_diffrn_orient_matrix_UB_22      -0.0300433000
_diffrn_orient_matrix_UB_23      -0.0393651000
_diffrn_orient_matrix_UB_31      -0.0206218000
_diffrn_orient_matrix_UB_32      0.0721573000
_diffrn_orient_matrix_UB_33      -0.0184117000
_diffrn_radiation_collimation    0.2
_diffrn_radiation_monochromator  'Confocal mirrors, VHF Varimax'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           55.0
_diffrn_source_power             2.475
_diffrn_source_target            Mo
_diffrn_source_type              'Rigaku FRE+'
_diffrn_source_voltage           45.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2687
_reflns_number_total             4111
_reflns_odcompleteness_completeness 99.90
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.42
_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       'CrysAlisPro 1.171.39.34b (Rigaku OD, 2017)'
_computing_data_collection       'CrystalClear-SM Expert 3.1 b27 (Rigaku, 2013)'
_computing_data_reduction        'CrysAlisPro 1.171.39.34b (Rigaku OD, 2017)'
_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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.988
_refine_diff_density_min         -0.374
_refine_diff_density_rms         0.109
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.103
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     355
_refine_ls_number_reflns         4111
_refine_ls_number_restraints     378
_refine_ls_R_factor_all          0.1438
_refine_ls_R_factor_gt           0.0969
_refine_ls_restrained_S_all      1.064
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1067P)²+7.5167P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2411
_refine_ls_wR_factor_ref         0.2652
_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
P1 \\sim P1A \\sim F1 \\sim F2 \\sim F3 \\sim F4 \\sim F5 \\sim F6 \\sim F1A
\\sim F2A \\sim F3A \\sim F4A \\sim F5A \\sim F6A: within 2A with sigma of 0.04
and sigma for terminal atoms of 0.08
P1 \\sim P1A: within 2A with sigma of 0.003 and sigma for terminal atoms of
0.006
3. Rigid body (RIGU) restrains
 P1, P1A, F1, F2, F3, F4, F5, F6, F1A, F2A, F3A, F4A, F5A, F6A
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Others
 Sof(P1A)=Sof(F1A)=Sof(F2A)=Sof(F3A)=Sof(F4A)=Sof(F5A)=Sof(F6A)=1-FVAR(1)
 Sof(P1)=Sof(F1)=Sof(F2)=Sof(F3)=Sof(F4)=Sof(F5)=Sof(F6)=FVAR(1)
5.a Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C14(H14A,H14B), C17(H17A,H17B), C18(H18A,H18B), C19(H19A,H19B)
5.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C8(H8), C11(H11), C12(H12), C16(H16)
5.c Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C20(H20A,H20B,H20C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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
O1 O 0.5200(2) 0.8998(5) 0.4063(2) 0.0362(10) Uani 1 1 d . . . . .
O2 O 0.4369(2) 0.3798(5) 0.3374(2) 0.0339(9) Uani 1 1 d . . . . .
N1 N 0.4789(3) 0.6415(5) 0.3714(2) 0.0250(10) Uani 1 1 d . . . . .
N2 N 0.0587(3) 0.6826(5) 0.3345(2) 0.0250(10) Uani 1 1 d . . . . .
N3 N -0.0846(3) 0.6830(6) 0.2884(3) 0.0306(11) Uani 1 1 d . . . . .
C1 C 0.4611(3) 0.8018(7) 0.3901(3) 0.0288(12) Uani 1 1 d . . . . .
C2 C 0.4157(3) 0.5186(7) 0.3496(3) 0.0252(12) Uani 1 1 d . . . . .
C3 C 0.3225(3) 0.5649(6) 0.3425(3) 0.0227(11) Uani 1 1 d . . . . .
C4 C 0.3024(3) 0.7247(7) 0.3655(3) 0.0250(11) Uani 1 1 d . . . . .
C5 C 0.3686(3) 0.8410(7) 0.3912(3) 0.0276(12) Uani 1 1 d . . . . .
C6 C 0.3493(4) 0.9949(7) 0.4123(3) 0.0322(13) Uani 1 1 d . . . . .
H6 H 0.3949 1.0727 0.4294 0.039 Uiso 1 1 calc R . . . .
C7 C 0.2617(4) 1.0366(7) 0.4086(3) 0.0342(14) Uani 1 1 d . . . . .
H7 H 0.2483 1.1433 0.4234 0.041 Uiso 1 1 calc R . . . .
C8 C 0.1947(4) 0.9256(7) 0.3839(3) 0.0316(13) Uani 1 1 d . . . . .
H8 H 0.1356 0.9568 0.3813 0.038 Uiso 1 1 calc R . . . .
C9 C 0.2129(3) 0.7659(6) 0.3625(3) 0.0249(12) Uani 1 1 d . . . . .
C10 C 0.1481(3) 0.6446(7) 0.3359(3) 0.0253(12) Uani 1 1 d . . . . .
C11 C 0.1689(3) 0.4943(7) 0.3118(3) 0.0265(12) Uani 1 1 d . . . . .
H11 H 0.1235 0.4173 0.2918 0.032 Uiso 1 1 calc R . . . .
C12 C 0.2571(3) 0.4526(7) 0.3162(3) 0.0269(12) Uani 1 1 d . . . . .
H12 H 0.2713 0.3466 0.3011 0.032 Uiso 1 1 calc R . . . .
C13 C 0.5702(3) 0.6014(7) 0.3713(3) 0.0302(13) Uani 1 1 d . . . . .
H13A H 0.5973 0.6957 0.3502 0.036 Uiso 1 1 calc R . . . .
H13B H 0.5702 0.5092 0.3333 0.036 Uiso 1 1 calc R . . . .
C14 C 0.6257(3) 0.5567(8) 0.4560(3) 0.0330(14) Uani 1 1 d . . . . .
H14A H 0.6060 0.4507 0.4730 0.040 Uiso 1 1 calc R . . . .
H14B H 0.6179 0.6396 0.4965 0.040 Uiso 1 1 calc R . . . .
C15 C 0.7225(4) 0.5464(8) 0.4551(3) 0.0397(15) Uani 1 1 d . . . . .
H15A H 0.7576 0.5205 0.5104 0.060 Uiso 1 1 calc GR . . . .
H15B H 0.7417 0.6508 0.4374 0.060 Uiso 1 1 calc GR . . . .
H15C H 0.7305 0.4611 0.4167 0.060 Uiso 1 1 calc GR . . . .
C16 C -0.0090(3) 0.6650(6) 0.2705(3) 0.0263(12) Uani 1 1 d . . . . .
H16 H -0.0030 0.6414 0.2166 0.032 Uiso 1 1 calc R . . . .
C17 C 0.0264(4) 0.7054(8) 0.4114(3) 0.0382(14) Uani 1 1 d . . . . .
H17A H 0.0497 0.8068 0.4404 0.046 Uiso 1 1 calc R . . . .
H17B H 0.0431 0.6123 0.4495 0.046 Uiso 1 1 calc R . . . .
C18 C -0.0725(3) 0.7142(7) 0.3773(3) 0.0321(13) Uani 1 1 d . . . . .
H18A H -0.1029 0.6307 0.4029 0.038 Uiso 1 1 calc R . . . .
H18B H -0.0953 0.8227 0.3869 0.038 Uiso 1 1 calc R . . . .
C19 C -0.1718(4) 0.6750(7) 0.2333(4) 0.0367(14) Uani 1 1 d . . . . .
H19A H -0.2003 0.7826 0.2321 0.044 Uiso 1 1 calc R . . . .
H19B H -0.2076 0.5958 0.2555 0.044 Uiso 1 1 calc R . . . .
C20 C -0.1721(4) 0.6265(9) 0.1458(4) 0.0488(18) Uani 1 1 d . . . . .
H20A H -0.1461 0.5182 0.1460 0.073 Uiso 1 1 calc GR . . . .
H20B H -0.1376 0.7051 0.1228 0.073 Uiso 1 1 calc GR . . . .
H20C H -0.2329 0.6250 0.1122 0.073 Uiso 1 1 calc GR . . . .
P1 P 0.5509(18) 0.728(2) 0.1411(16) 0.0267(19) Uani 0.478(12) 1 d . U P A 1
P1A P 0.5500(16) 0.6960(16) 0.1451(14) 0.0225(16) Uani 0.522(12) 1 d . U P A 2
F1 F 0.5119(9) 0.5925(11) 0.0710(5) 0.057(3) Uani 0.478(12) 1 d . U P A 1
F2 F 0.6154(8) 0.5824(12) 0.1926(7) 0.039(3) Uani 0.478(12) 1 d . U P A 1
F3 F 0.4753(5) 0.6530(16) 0.1881(5) 0.048(3) Uani 0.478(12) 1 d . U P A 1
F4 F 0.4841(7) 0.8448(14) 0.0956(6) 0.045(3) Uani 0.478(12) 1 d . U P A 1
F5 F 0.6211(7) 0.7750(17) 0.0996(7) 0.049(3) Uani 0.478(12) 1 d . U P A 1
F6 F 0.5818(10) 0.8418(12) 0.2172(6) 0.060(3) Uani 0.478(12) 1 d . U P A 1
F1A F 0.5808(8) 0.5950(9) 0.0765(4) 0.052(3) Uani 0.522(12) 1 d . U P A 2
F2A F 0.6367(7) 0.6525(17) 0.2087(7) 0.054(3) Uani 0.522(12) 1 d . U P A 2
F3A F 0.5032(6) 0.5567(11) 0.1725(5) 0.047(2) Uani 0.522(12) 1 d . U P A 2
F4A F 0.4636(7) 0.7515(19) 0.0781(6) 0.070(3) Uani 0.522(12) 1 d . U P A 2
F5A F 0.6043(9) 0.8501(13) 0.1144(7) 0.063(3) Uani 0.522(12) 1 d . U P A 2
F6A F 0.5258(8) 0.8190(11) 0.2108(5) 0.048(3) Uani 0.522(12) 1 d . U P A 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
O1 C1 1.205(6) . ?
O2 C2 1.221(6) . ?
N1 C1 1.400(7) . ?
N1 C2 1.400(7) . ?
N1 C13 1.467(6) . ?
N2 C10 1.428(6) . ?
N2 C16 1.318(6) . ?
N2 C17 1.506(7) . ?
N3 C16 1.299(7) . ?
N3 C18 1.477(7) . ?
N3 C19 1.451(7) . ?
C1 C5 1.487(7) . ?
C2 C3 1.484(7) . ?
C3 C4 1.428(7) . ?
C3 C12 1.370(7) . ?
C4 C5 1.399(7) . ?
C4 C9 1.429(7) . ?
C5 C6 1.369(8) . ?
C6 H6 0.9500 . ?
C6 C7 1.399(8) . ?
C7 H7 0.9500 . ?
C7 C8 1.377(8) . ?
C8 H8 0.9500 . ?
C8 C9 1.410(8) . ?
C9 C10 1.417(7) . ?
C10 C11 1.366(8) . ?
C11 H11 0.9500 . ?
C11 C12 1.406(7) . ?
C12 H12 0.9500 . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C14 1.518(7) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 C15 1.520(8) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16 0.9500 . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C17 C18 1.516(7) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C19 C20 1.517(9) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
P1 F1 1.63(2) . ?
P1 F2 1.67(2) . ?
P1 F3 1.69(3) . ?
P1 F4 1.49(2) . ?
P1 F5 1.49(3) . ?
P1 F6 1.56(3) . ?
P1A F1A 1.58(2) . ?
P1A F2A 1.55(2) . ?
P1A F3A 1.492(19) . ?
P1A F4A 1.60(2) . ?
P1A F5A 1.68(2) . ?
P1A F6A 1.61(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C2 124.9(4) . . ?
C1 N1 C13 117.4(4) . . ?
C2 N1 C13 117.6(5) . . ?
C10 N2 C17 123.0(4) . . ?
C16 N2 C10 125.4(4) . . ?
C16 N2 C17 109.8(4) . . ?
C16 N3 C18 110.6(4) . . ?
C16 N3 C19 128.0(5) . . ?
C19 N3 C18 121.4(5) . . ?
O1 C1 N1 119.9(5) . . ?
O1 C1 C5 123.0(5) . . ?
N1 C1 C5 117.1(5) . . ?
O2 C2 N1 121.1(5) . . ?
O2 C2 C3 121.9(5) . . ?
N1 C2 C3 117.0(5) . . ?
C4 C3 C2 119.5(4) . . ?
C12 C3 C2 119.7(5) . . ?
C12 C3 C4 120.8(5) . . ?
C3 C4 C9 119.2(5) . . ?
C5 C4 C3 121.2(5) . . ?
C5 C4 C9 119.6(5) . . ?
C4 C5 C1 119.9(5) . . ?
C6 C5 C1 118.7(5) . . ?
C6 C5 C4 121.3(5) . . ?
C5 C6 H6 120.3 . . ?
C5 C6 C7 119.4(5) . . ?
C7 C6 H6 120.3 . . ?
C6 C7 H7 119.4 . . ?
C8 C7 C6 121.1(6) . . ?
C8 C7 H7 119.4 . . ?
C7 C8 H8 119.7 . . ?
C7 C8 C9 120.5(5) . . ?
C9 C8 H8 119.7 . . ?
C8 C9 C4 118.0(5) . . ?
C8 C9 C10 124.2(5) . . ?
C10 C9 C4 117.7(5) . . ?
C9 C10 N2 118.4(5) . . ?
C11 C10 N2 119.8(5) . . ?
C11 C10 C9 121.8(5) . . ?
C10 C11 H11 119.8 . . ?
C10 C11 C12 120.5(5) . . ?
C12 C11 H11 119.8 . . ?
C3 C12 C11 119.9(5) . . ?
C3 C12 H12 120.0 . . ?
C11 C12 H12 120.0 . . ?
N1 C13 H13A 109.0 . . ?
N1 C13 H13B 109.0 . . ?
N1 C13 C14 112.9(4) . . ?
H13A C13 H13B 107.8 . . ?
C14 C13 H13A 109.0 . . ?
C14 C13 H13B 109.0 . . ?
C13 C14 H14A 109.6 . . ?
C13 C14 H14B 109.6 . . ?
C13 C14 C15 110.4(5) . . ?
H14A C14 H14B 108.1 . . ?
C15 C14 H14A 109.6 . . ?
C15 C14 H14B 109.6 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N2 C16 H16 123.3 . . ?
N3 C16 N2 113.4(5) . . ?
N3 C16 H16 123.3 . . ?
N2 C17 H17A 111.4 . . ?
N2 C17 H17B 111.4 . . ?
N2 C17 C18 102.0(4) . . ?
H17A C17 H17B 109.2 . . ?
C18 C17 H17A 111.4 . . ?
C18 C17 H17B 111.4 . . ?
N3 C18 C17 103.9(4) . . ?
N3 C18 H18A 111.0 . . ?
N3 C18 H18B 111.0 . . ?
C17 C18 H18A 111.0 . . ?
C17 C18 H18B 111.0 . . ?
H18A C18 H18B 109.0 . . ?
N3 C19 H19A 108.7 . . ?
N3 C19 H19B 108.7 . . ?
N3 C19 C20 114.1(5) . . ?
H19A C19 H19B 107.6 . . ?
C20 C19 H19A 108.7 . . ?
C20 C19 H19B 108.7 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
F1 P1 F2 87.3(10) . . ?
F1 P1 F3 84.4(11) . . ?
F2 P1 F3 84.3(10) . . ?
F4 P1 F1 88.8(14) . . ?
F4 P1 F2 172.9(18) . . ?
F4 P1 F3 89.4(15) . . ?
F4 P1 F6 94.1(12) . . ?
F5 P1 F1 91.7(15) . . ?
F5 P1 F2 90.3(15) . . ?
F5 P1 F3 173.5(15) . . ?
F5 P1 F4 95.7(13) . . ?
F5 P1 F6 96.3(14) . . ?
F6 P1 F1 171.2(17) . . ?
F6 P1 F2 88.9(13) . . ?
F6 P1 F3 87.3(14) . . ?
F1A P1A F4A 89.8(13) . . ?
F1A P1A F5A 84.8(12) . . ?
F1A P1A F6A 172.2(14) . . ?
F2A P1A F1A 90.5(13) . . ?
F2A P1A F4A 176.2(14) . . ?
F2A P1A F5A 87.8(13) . . ?
F2A P1A F6A 89.3(13) . . ?
F3A P1A F1A 94.5(10) . . ?
F3A P1A F2A 91.4(11) . . ?
F3A P1A F4A 92.3(13) . . ?
F3A P1A F5A 178.9(17) . . ?
F3A P1A F6A 93.3(14) . . ?
F4A P1A F5A 88.5(10) . . ?
F4A P1A F6A 90.0(12) . . ?
F6A P1A F5A 87.4(9) . . ?

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
O1 C1 C5 C4 175.1(5) . . . . ?
O1 C1 C5 C6 -0.7(8) . . . . ?
O2 C2 C3 C4 173.7(5) . . . . ?
O2 C2 C3 C12 -4.4(8) . . . . ?
N1 C1 C5 C4 -6.7(7) . . . . ?
N1 C1 C5 C6 177.5(4) . . . . ?
N1 C2 C3 C4 -6.1(7) . . . . ?
N1 C2 C3 C12 175.8(4) . . . . ?
N1 C13 C14 C15 -169.8(5) . . . . ?
N2 C10 C11 C12 -177.2(4) . . . . ?
N2 C17 C18 N3 4.3(6) . . . . ?
C1 N1 C2 O2 -177.0(5) . . . . ?
C1 N1 C2 C3 2.8(7) . . . . ?
C1 N1 C13 C14 85.8(6) . . . . ?
C1 C5 C6 C7 176.0(5) . . . . ?
C2 N1 C1 O1 -178.3(5) . . . . ?
C2 N1 C1 C5 3.5(7) . . . . ?
C2 N1 C13 C14 -96.7(6) . . . . ?
C2 C3 C4 C5 3.0(7) . . . . ?
C2 C3 C4 C9 -176.8(4) . . . . ?
C2 C3 C12 C11 178.1(4) . . . . ?
C3 C4 C5 C1 3.5(7) . . . . ?
C3 C4 C5 C6 179.2(5) . . . . ?
C3 C4 C9 C8 -178.7(4) . . . . ?
C3 C4 C9 C10 -0.5(7) . . . . ?
C4 C3 C12 C11 0.0(7) . . . . ?
C4 C5 C6 C7 0.3(8) . . . . ?
C4 C9 C10 N2 178.5(4) . . . . ?
C4 C9 C10 C11 -1.6(7) . . . . ?
C5 C4 C9 C8 1.5(7) . . . . ?
C5 C4 C9 C10 179.7(4) . . . . ?
C5 C6 C7 C8 -0.1(8) . . . . ?
C6 C7 C8 C9 0.7(8) . . . . ?
C7 C8 C9 C4 -1.3(7) . . . . ?
C7 C8 C9 C10 -179.4(5) . . . . ?
C8 C9 C10 N2 -3.4(7) . . . . ?
C8 C9 C10 C11 176.5(5) . . . . ?
C9 C4 C5 C1 -176.7(4) . . . . ?
C9 C4 C5 C6 -1.0(7) . . . . ?
C9 C10 C11 C12 2.9(8) . . . . ?
C10 N2 C16 N3 169.5(5) . . . . ?
C10 N2 C17 C18 -170.8(5) . . . . ?
C10 C11 C12 C3 -2.1(8) . . . . ?
C12 C3 C4 C5 -179.0(5) . . . . ?
C12 C3 C4 C9 1.2(7) . . . . ?
C13 N1 C1 O1 -1.1(7) . . . . ?
C13 N1 C1 C5 -179.3(4) . . . . ?
C13 N1 C2 O2 5.7(7) . . . . ?
C13 N1 C2 C3 -174.4(4) . . . . ?
C16 N2 C10 C9 127.0(5) . . . . ?
C16 N2 C10 C11 -53.0(7) . . . . ?
C16 N2 C17 C18 -5.5(6) . . . . ?
C16 N3 C18 C17 -2.1(6) . . . . ?
C16 N3 C19 C20 5.1(9) . . . . ?
C17 N2 C10 C9 -70.1(7) . . . . ?
C17 N2 C10 C11 110.0(6) . . . . ?
C17 N2 C16 N3 4.6(6) . . . . ?
C18 N3 C16 N2 -1.6(6) . . . . ?
C18 N3 C19 C20 -174.6(5) . . . . ?
C19 N3 C16 N2 178.7(5) . . . . ?
C19 N3 C18 C17 177.7(5) . . . . ?

_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a MITIGEN holder in perfluoroether oil'
_olex2_submission_original_sample_id LG215
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_full_max 2.646
_oxdiff_exptl_absorpt_empirical_full_min 0.435
####################################################################### 
# 
# 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_AuClL3
_database_code_depnum_ccdc_archive 'CCDC 1831225'
_audit_update_record             
;
2018-03-20 deposited with the CCDC.
2018-11-22 downloaded from the CCDC.
;

#2017ncs0222

_audit_creation_date             2018-03-19
_audit_creation_method           
;
Olex2 1.2-alpha
(compiled 2018.03.09 svn.r3491 for OlexSys, GUI svn.r5480)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H21 Au Cl N3 O2'
_chemical_formula_sum            'C20 H21 Au Cl N3 O2'
_chemical_formula_weight         567.81
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C20 H21 N3 O2 Cl Au'
_chemical_oxdiff_usercomment     'LG220 - recollection previously split crystal'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Au Au -2.0133 8.8022 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   9.0951(2)
_cell_length_b                   10.0127(2)
_cell_length_c                   12.2157(3)
_cell_angle_alpha                67.576(2)
_cell_angle_beta                 72.828(2)
_cell_angle_gamma                76.121(2)
_cell_volume                     972.23(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    31702
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      31.7040
_cell_measurement_theta_min      1.8590
_shelx_estimated_absorpt_T_max   0.927
_shelx_estimated_absorpt_T_min   0.577
_exptl_absorpt_coefficient_mu    7.723
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.61492
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;


CrysAlisPro 1.171.39.28e (Rigaku Oxford Diffraction, 2015)

Empirical absorption correction using spherical harmonics,

 implemented in SCALE3 ABSPACK scaling algorithm.

;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'light yellow'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.940
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             548
_exptl_crystal_recrystallization_method 
'The material was recrystallised from ether'
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0413
_diffrn_reflns_av_unetI/netI     0.0162
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            50364
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.483
_diffrn_reflns_theta_min         1.852
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'hybrid pixel detector'
_diffrn_detector_area_resol_mean 10
_diffrn_detector_dtime           0.000
_diffrn_detector_type            'Rigaku, HyPix 6000'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;


List of Runs (angles in degrees, time in seconds):



  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames

#--------------------------------------------------------------------------

  1  ω    -45.00  81.00   0.50    2.00    --   -8.10  38.00  60.00  252

  2  ω    -45.00  81.00   0.50    2.00    --   -8.10  38.00 -90.00  252

  3  ω    -97.00  26.00   0.50    2.00    --   -8.10 -65.00 -60.00  246

  4  ω    -97.00  26.00   0.50    2.00    --   -8.10 -65.00  60.00  246

  5  ω    -97.00  25.00   0.50    2.00    --   -8.10 -57.00-150.00  244

  6  ω    -42.00  81.00   0.50    2.00    --   -8.10  65.00 -30.00  246

  7  ω    -45.00  81.00   0.50    2.00    --   -8.10  38.00 150.00  252

  8  ω    -84.00  94.00   0.50    2.00    --    5.00   0.00-180.00  356

  9  ω    -41.00  81.00   0.50    2.00    --   -8.10  57.00  90.00  244

 10  ω    -42.00  81.00   0.50    2.00    --   -8.10  65.00 -90.00  246

 11  ω    -97.00  29.00   0.50    2.00    --   -8.10 -38.00 120.00  252

 12  ω    -41.00  81.00   0.50    2.00    --   -8.10  57.00 -60.00  244

 13  ω    -41.00  81.00   0.50    2.00    --   -8.10  57.00-180.00  244

 14  ω    -84.00 -59.00   0.50    2.00    --    5.00   0.00-150.00   50

;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_details 'Rigaku, AFC12 κ goniometer'
_diffrn_measurement_device_type  
'Rigaku FRE+ equipped with VHF Varimax confocal mirrors and an AFC12 goniometer and HyPix 6000 detector'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support 'MiTeGen MicroLoop'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0506954000
_diffrn_orient_matrix_UB_12      -0.0502732000
_diffrn_orient_matrix_UB_13      0.0418373000
_diffrn_orient_matrix_UB_21      0.0118171000
_diffrn_orient_matrix_UB_22      0.0149560000
_diffrn_orient_matrix_UB_23      0.0488064000
_diffrn_orient_matrix_UB_31      -0.0639866000
_diffrn_orient_matrix_UB_32      0.0569767000
_diffrn_orient_matrix_UB_33      -0.0052567000
_diffrn_radiation_collimation    0.2
_diffrn_radiation_monochromator  'Confocal mirrors, VHF Varimax'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           55.0
_diffrn_source_power             2.475
_diffrn_source_target            Mo
_diffrn_source_type              'Rigaku FRE+'
_diffrn_source_voltage           45.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4313
_reflns_number_total             4450
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.42
_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       'CrysAlisPro 1.171.39.28e (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.28e (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.28e (Rigaku OD, 2015)'
_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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.731
_refine_diff_density_min         -0.747
_refine_diff_density_rms         0.083
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     275
_refine_ls_number_reflns         4450
_refine_ls_number_restraints     35
_refine_ls_R_factor_all          0.0142
_refine_ls_R_factor_gt           0.0133
_refine_ls_restrained_S_all      1.045
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0166P)²+0.7625P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0322
_refine_ls_wR_factor_ref         0.0324
_refine_special_details          
'The propyl chain is disordered over 2 positions. As such various restraints (SADI, RIGU) have been applied.'
_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. Restrained distances
 C19B-C20B \\sim C20-C19
 with sigma of 0.02
 C19B-N3 \\sim N3-C19
 with sigma of 0.02
 C18B-C20B \\sim C20-C18
 with sigma of 0.02
 C18B-N3 \\sim N3-C18
 with sigma of 0.02
 C19B-C18B \\sim C18-C19
 with sigma of 0.02
3. Rigid body (RIGU) restrains
 N3, C18, C19, C20, C19B, C20B, C18B
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4. Others
 Sof(C19B)=Sof(H19C)=Sof(H19D)=Sof(C20B)=Sof(H20D)=Sof(H20E)=Sof(H20F)=
 Sof(C18B)=Sof(H18C)=Sof(H18D)=1-FVAR(1)
 Sof(C18)=Sof(H18A)=Sof(H18B)=Sof(C19)=Sof(H19A)=Sof(H19B)=Sof(C20)=Sof(H20A)=
 Sof(H20B)=Sof(H20C)=FVAR(1)
5.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C16(H16A,H16B), C18(H18A,H18B), C19(H19A,H19B),
 C19B(H19C,H19D), C18B(H18C,H18D)
5.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C11(H11), C12(H12), C13(H13)
5.c Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C20(H20A,H20B,H20C), C20B(H20D,H20E,H20F)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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 0.19101(2) 0.47344(2) 0.48438(2) 0.01246(3) Uani 1 1 d . . . . .
Cl1 Cl 0.24144(6) 0.40958(5) 0.31405(4) 0.01749(10) Uani 1 1 d . . . . .
O1 O 0.63586(18) 1.10753(17) 0.24440(15) 0.0235(3) Uani 1 1 d . . . . .
O2 O 0.20511(19) 1.25811(17) 0.08819(14) 0.0236(3) Uani 1 1 d . . . . .
N1 N 0.2136(2) 0.63159(18) 0.64094(15) 0.0146(3) Uani 1 1 d . . . . .
N2 N 0.1217(2) 0.42737(18) 0.74734(15) 0.0158(3) Uani 1 1 d . . . . .
N3 N 0.4234(2) 1.17904(18) 0.16263(16) 0.0168(3) Uani 1 1 d D U . . .
C1 C 0.1687(2) 0.5146(2) 0.63544(18) 0.0135(4) Uani 1 1 d . . . . .
C2 C 0.2263(3) 0.6033(2) 0.76624(18) 0.0201(4) Uani 1 1 d . . . . .
H2A H 0.1937 0.6931 0.7884 0.024 Uiso 1 1 calc R . . . .
H2B H 0.3332 0.5607 0.7773 0.024 Uiso 1 1 calc R . . . .
C3 C 0.1127(3) 0.4940(2) 0.83812(19) 0.0196(4) Uani 1 1 d . . . . .
H3A H 0.1466 0.4211 0.9111 0.024 Uiso 1 1 calc R . . . .
H3B H 0.0064 0.5430 0.8628 0.024 Uiso 1 1 calc R . . . .
C4 C 0.2852(2) 0.7431(2) 0.54080(18) 0.0140(4) Uani 1 1 d . . . . .
C5 C 0.4333(2) 0.7611(2) 0.53358(19) 0.0180(4) Uani 1 1 d . . . . .
H5 H 0.4875 0.6966 0.5940 0.022 Uiso 1 1 calc R . . . .
C6 C 0.5050(2) 0.8734(2) 0.4382(2) 0.0188(4) Uani 1 1 d . . . . .
H6 H 0.6075 0.8843 0.4343 0.023 Uiso 1 1 calc R . . . .
C7 C 0.4289(2) 0.9683(2) 0.35012(18) 0.0143(4) Uani 1 1 d . . . . .
C8 C 0.5056(2) 1.0878(2) 0.25100(19) 0.0173(4) Uani 1 1 d . . . . .
C9 C 0.2714(3) 1.1707(2) 0.16602(18) 0.0168(4) Uani 1 1 d . . . . .
C10 C 0.1951(2) 1.0528(2) 0.26775(18) 0.0143(4) Uani 1 1 d . . . . .
C11 C 0.0442(2) 1.0415(2) 0.27551(19) 0.0179(4) Uani 1 1 d . . . . .
H11 H -0.0080 1.1066 0.2141 0.021 Uiso 1 1 calc R . . . .
C12 C -0.0325(2) 0.9342(2) 0.3737(2) 0.0188(4) Uani 1 1 d . . . . .
H12 H -0.1379 0.9296 0.3800 0.023 Uiso 1 1 calc R . . . .
C13 C 0.0427(2) 0.8356(2) 0.46102(19) 0.0153(4) Uani 1 1 d . . . . .
H13 H -0.0109 0.7634 0.5270 0.018 Uiso 1 1 calc R . . . .
C14 C 0.2003(2) 0.8409(2) 0.45345(17) 0.0125(4) Uani 1 1 d . . . . .
C15 C 0.2754(2) 0.9538(2) 0.35661(17) 0.0122(4) Uani 1 1 d . . . . .
C16 C 0.0473(3) 0.2989(2) 0.7817(2) 0.0214(4) Uani 1 1 d . . . . .
H16A H 0.0434 0.2837 0.7072 0.026 Uiso 1 1 calc R . . . .
H16B H -0.0609 0.3161 0.8276 0.026 Uiso 1 1 calc R . . . .
C17 C 0.1328(3) 0.1629(2) 0.8585(2) 0.0301(5) Uani 1 1 d . . . . .
H17A H 0.2403 0.1460 0.8137 0.045 Uiso 1 1 calc GR . . . .
H17B H 0.0809 0.0789 0.8775 0.045 Uiso 1 1 calc GR . . . .
H17C H 0.1324 0.1756 0.9343 0.045 Uiso 1 1 calc GR . . . .
C18 C 0.5006(7) 1.3030(4) 0.0697(3) 0.0199(13) Uani 0.868(7) 1 d D U P A 1
H18A H 0.5536 1.3411 0.1093 0.024 Uiso 0.868(7) 1 calc R . P A 1
H18B H 0.4202 1.3822 0.0364 0.024 Uiso 0.868(7) 1 calc R . P A 1
C19 C 0.6187(4) 1.2633(3) -0.0346(3) 0.0338(9) Uani 0.868(7) 1 d D U P A 1
H19A H 0.6732 1.3483 -0.0873 0.041 Uiso 0.868(7) 1 calc R . P A 1
H19B H 0.6972 1.1822 -0.0008 0.041 Uiso 0.868(7) 1 calc R . P A 1
C20 C 0.5508(5) 1.2183(4) -0.1124(3) 0.0462(11) Uani 0.868(7) 1 d D U P A 1
H20A H 0.6338 1.1979 -0.1788 0.069 Uiso 0.868(7) 1 calc GR . P A 1
H20B H 0.4724 1.2974 -0.1462 0.069 Uiso 0.868(7) 1 calc GR . P A 1
H20C H 0.5023 1.1303 -0.0624 0.069 Uiso 0.868(7) 1 calc GR . P A 1
C19B C 0.535(2) 1.2799(17) -0.0628(12) 0.024(4) Uani 0.132(7) 1 d D U P A 2
H19C H 0.4481 1.2648 -0.0879 0.029 Uiso 0.132(7) 1 calc R . P A 2
H19D H 0.5768 1.3679 -0.1253 0.029 Uiso 0.132(7) 1 calc R . P A 2
C20B C 0.660(2) 1.1518(18) -0.0610(16) 0.028(5) Uani 0.132(7) 1 d D U P A 2
H20D H 0.7110 1.1555 -0.1447 0.042 Uiso 0.132(7) 1 calc GR . P A 2
H20E H 0.6138 1.0614 -0.0172 0.042 Uiso 0.132(7) 1 calc GR . P A 2
H20F H 0.7364 1.1544 -0.0201 0.042 Uiso 0.132(7) 1 calc GR . P A 2
C18B C 0.471(4) 1.309(2) 0.0580(17) 0.015(6) Uani 0.132(7) 1 d D U P A 2
H18C H 0.5511 1.3459 0.0744 0.018 Uiso 0.132(7) 1 calc R . P A 2
H18D H 0.3798 1.3869 0.0502 0.018 Uiso 0.132(7) 1 calc R . P A 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 Au1 3.31459(15) 2_566 ?
Au1 Cl1 2.2933(5) . ?
Au1 C1 1.984(2) . ?
O1 C8 1.222(3) . ?
O2 C9 1.218(3) . ?
N1 C1 1.359(2) . ?
N1 C2 1.481(2) . ?
N1 C4 1.416(3) . ?
N2 C1 1.318(3) . ?
N2 C3 1.472(3) . ?
N2 C16 1.458(3) . ?
N3 C8 1.398(3) . ?
N3 C9 1.392(3) . ?
N3 C18 1.481(4) . ?
N3 C18B 1.481(17) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.519(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.374(3) . ?
C4 C14 1.422(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.396(3) . ?
C6 H6 0.9500 . ?
C6 C7 1.373(3) . ?
C7 C8 1.477(3) . ?
C7 C15 1.413(3) . ?
C9 C10 1.478(3) . ?
C10 C11 1.377(3) . ?
C10 C15 1.412(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.401(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.372(3) . ?
C13 H13 0.9500 . ?
C13 C14 1.421(3) . ?
C14 C15 1.421(3) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 C17 1.513(3) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C18 C19 1.520(4) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C19 C20 1.514(5) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C19B H19C 0.9900 . ?
C19B H19D 0.9900 . ?
C19B C20B 1.492(16) . ?
C19B C18B 1.531(16) . ?
C20B H20D 0.9800 . ?
C20B H20E 0.9800 . ?
C20B H20F 0.9800 . ?
C18B H18C 0.9900 . ?
C18B H18D 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
Cl1 Au1 Au1 93.510(13) . 2_566 ?
C1 Au1 Au1 91.94(6) . 2_566 ?
C1 Au1 Cl1 173.76(6) . . ?
C1 N1 C2 109.93(16) . . ?
C1 N1 C4 126.02(17) . . ?
C4 N1 C2 121.29(16) . . ?
C1 N2 C3 111.84(16) . . ?
C1 N2 C16 125.76(18) . . ?
C16 N2 C3 120.53(17) . . ?
C8 N3 C18 115.3(3) . . ?
C8 N3 C18B 127.9(17) . . ?
C9 N3 C8 124.58(17) . . ?
C9 N3 C18 119.6(3) . . ?
C9 N3 C18B 107.2(17) . . ?
N1 C1 Au1 125.36(14) . . ?
N2 C1 Au1 125.93(15) . . ?
N2 C1 N1 108.44(17) . . ?
N1 C2 H2A 111.7 . . ?
N1 C2 H2B 111.7 . . ?
N1 C2 C3 100.34(16) . . ?
H2A C2 H2B 109.5 . . ?
C3 C2 H2A 111.7 . . ?
C3 C2 H2B 111.7 . . ?
N2 C3 C2 100.69(16) . . ?
N2 C3 H3A 111.6 . . ?
N2 C3 H3B 111.6 . . ?
C2 C3 H3A 111.6 . . ?
C2 C3 H3B 111.6 . . ?
H3A C3 H3B 109.4 . . ?
N1 C4 C14 119.88(17) . . ?
C5 C4 N1 119.27(18) . . ?
C5 C4 C14 120.72(18) . . ?
C4 C5 H5 119.7 . . ?
C4 C5 C6 120.58(19) . . ?
C6 C5 H5 119.7 . . ?
C5 C6 H6 119.6 . . ?
C7 C6 C5 120.75(19) . . ?
C7 C6 H6 119.6 . . ?
C6 C7 C8 119.96(18) . . ?
C6 C7 C15 119.81(18) . . ?
C15 C7 C8 120.20(18) . . ?
O1 C8 N3 120.37(19) . . ?
O1 C8 C7 122.4(2) . . ?
N3 C8 C7 117.27(18) . . ?
O2 C9 N3 120.77(19) . . ?
O2 C9 C10 122.0(2) . . ?
N3 C9 C10 117.21(18) . . ?
C11 C10 C9 119.19(18) . . ?
C11 C10 C15 120.37(18) . . ?
C15 C10 C9 120.44(18) . . ?
C10 C11 H11 119.9 . . ?
C10 C11 C12 120.18(19) . . ?
C12 C11 H11 119.9 . . ?
C11 C12 H12 119.6 . . ?
C13 C12 C11 120.81(19) . . ?
C13 C12 H12 119.6 . . ?
C12 C13 H13 119.8 . . ?
C12 C13 C14 120.46(18) . . ?
C14 C13 H13 119.8 . . ?
C13 C14 C4 123.58(18) . . ?
C15 C14 C4 117.87(17) . . ?
C15 C14 C13 118.48(18) . . ?
C7 C15 C14 120.23(18) . . ?
C10 C15 C7 120.17(18) . . ?
C10 C15 C14 119.59(17) . . ?
N2 C16 H16A 109.2 . . ?
N2 C16 H16B 109.2 . . ?
N2 C16 C17 112.15(19) . . ?
H16A C16 H16B 107.9 . . ?
C17 C16 H16A 109.2 . . ?
C17 C16 H16B 109.2 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
N3 C18 H18A 108.8 . . ?
N3 C18 H18B 108.8 . . ?
N3 C18 C19 113.7(3) . . ?
H18A C18 H18B 107.7 . . ?
C19 C18 H18A 108.8 . . ?
C19 C18 H18B 108.8 . . ?
C18 C19 H19A 108.6 . . ?
C18 C19 H19B 108.6 . . ?
H19A C19 H19B 107.6 . . ?
C20 C19 C18 114.8(4) . . ?
C20 C19 H19A 108.6 . . ?
C20 C19 H19B 108.6 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
H19C C19B H19D 107.5 . . ?
C20B C19B H19C 108.4 . . ?
C20B C19B H19D 108.4 . . ?
C20B C19B C18B 115.4(15) . . ?
C18B C19B H19C 108.4 . . ?
C18B C19B H19D 108.4 . . ?
C19B C20B H20D 109.5 . . ?
C19B C20B H20E 109.5 . . ?
C19B C20B H20F 109.5 . . ?
H20D C20B H20E 109.5 . . ?
H20D C20B H20F 109.5 . . ?
H20E C20B H20F 109.5 . . ?
N3 C18B C19B 113.6(14) . . ?
N3 C18B H18C 108.8 . . ?
N3 C18B H18D 108.8 . . ?
C19B C18B H18C 108.8 . . ?
C19B C18B H18D 108.8 . . ?
H18C C18B H18D 107.7 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 C9 C10 C11 -0.3(3) . . . . ?
O2 C9 C10 C15 -179.74(18) . . . . ?
N1 C2 C3 N2 27.69(19) . . . . ?
N1 C4 C5 C6 -177.72(19) . . . . ?
N1 C4 C14 C13 1.1(3) . . . . ?
N1 C4 C14 C15 178.09(17) . . . . ?
N3 C9 C10 C11 179.26(18) . . . . ?
N3 C9 C10 C15 -0.1(3) . . . . ?
N3 C18 C19 C20 64.7(5) . . . . ?
C1 N1 C2 C3 -25.9(2) . . . . ?
C1 N1 C4 C5 -116.8(2) . . . . ?
C1 N1 C4 C14 67.3(3) . . . . ?
C1 N2 C3 C2 -23.6(2) . . . . ?
C1 N2 C16 C17 124.6(2) . . . . ?
C2 N1 C1 Au1 -161.98(15) . . . . ?
C2 N1 C1 N2 12.3(2) . . . . ?
C2 N1 C4 C5 42.4(3) . . . . ?
C2 N1 C4 C14 -133.50(19) . . . . ?
C3 N2 C1 Au1 -177.81(14) . . . . ?
C3 N2 C1 N1 7.9(2) . . . . ?
C3 N2 C16 C17 -72.3(3) . . . . ?
C4 N1 C1 Au1 -0.8(3) . . . . ?
C4 N1 C1 N2 173.54(18) . . . . ?
C4 N1 C2 C3 171.83(17) . . . . ?
C4 C5 C6 C7 0.2(3) . . . . ?
C4 C14 C15 C7 -1.1(3) . . . . ?
C4 C14 C15 C10 179.78(17) . . . . ?
C5 C4 C14 C13 -174.75(19) . . . . ?
C5 C4 C14 C15 2.2(3) . . . . ?
C5 C6 C7 C8 179.04(19) . . . . ?
C5 C6 C7 C15 0.9(3) . . . . ?
C6 C7 C8 O1 -0.8(3) . . . . ?
C6 C7 C8 N3 178.73(18) . . . . ?
C6 C7 C15 C10 178.67(18) . . . . ?
C6 C7 C15 C14 -0.4(3) . . . . ?
C8 N3 C9 O2 176.87(18) . . . . ?
C8 N3 C9 C10 -2.7(3) . . . . ?
C8 N3 C18 C19 83.8(5) . . . . ?
C8 N3 C18B C19B 101(3) . . . . ?
C8 C7 C15 C10 0.5(3) . . . . ?
C8 C7 C15 C14 -178.58(17) . . . . ?
C9 N3 C8 O1 -176.10(19) . . . . ?
C9 N3 C8 C7 4.3(3) . . . . ?
C9 N3 C18 C19 -103.9(4) . . . . ?
C9 N3 C18B C19B -86(3) . . . . ?
C9 C10 C11 C12 -177.47(19) . . . . ?
C9 C10 C15 C7 1.1(3) . . . . ?
C9 C10 C15 C14 -179.76(17) . . . . ?
C10 C11 C12 C13 -2.5(3) . . . . ?
C11 C10 C15 C7 -178.27(18) . . . . ?
C11 C10 C15 C14 0.9(3) . . . . ?
C11 C12 C13 C14 0.1(3) . . . . ?
C12 C13 C14 C4 179.56(18) . . . . ?
C12 C13 C14 C15 2.6(3) . . . . ?
C13 C14 C15 C7 176.05(17) . . . . ?
C13 C14 C15 C10 -3.1(3) . . . . ?
C14 C4 C5 C6 -1.9(3) . . . . ?
C15 C7 C8 O1 177.31(19) . . . . ?
C15 C7 C8 N3 -3.1(3) . . . . ?
C15 C10 C11 C12 1.9(3) . . . . ?
C16 N2 C1 Au1 -13.4(3) . . . . ?
C16 N2 C1 N1 172.31(19) . . . . ?
C16 N2 C3 C2 171.08(18) . . . . ?
C18 N3 C8 O1 -4.3(3) . . . . ?
C18 N3 C8 C7 176.2(2) . . . . ?
C18 N3 C9 O2 5.4(3) . . . . ?
C18 N3 C9 C10 -174.2(2) . . . . ?
C20B C19B C18B N3 -51(3) . . . . ?
C18B N3 C8 O1 -3.3(9) . . . . ?
C18B N3 C8 C7 177.1(9) . . . . ?
C18B N3 C9 O2 2.8(8) . . . . ?
C18B N3 C9 C10 -176.8(8) . . . . ?

_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a MITIGEN holder in perfluoroether oil'
_olex2_submission_original_sample_id LG220
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;


Empirical correction (ABSPACK) includes:

- Absorption correction using spherical harmonics

- Frame scaling

;
_oxdiff_exptl_absorpt_empirical_full_max 2.197
_oxdiff_exptl_absorpt_empirical_full_min 0.530
