# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_170929LT
_database_code_depnum_ccdc_archive 'CCDC 1829190'
_audit_update_record             
;
2018-03-13 deposited with the CCDC.
2018-12-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H15 N O3'
_chemical_formula_weight         305.32

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

_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   14.3845(14)
_cell_length_b                   4.3448(4)
_cell_length_c                   23.199(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1449.9(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    1821
_cell_measurement_theta_min      2.8321
_cell_measurement_theta_max      24.9996

_exptl_crystal_description       Tabullar
_exptl_crystal_colour            Red
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.399
_exptl_crystal_F_000             640
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.06
_exptl_absorpt_coefficient_mu    0.095
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8324
_exptl_absorpt_correction_T_max  0.9485
_exptl_absorpt_process_details   'SADABS V2014/4 (Bruker AXS Inc.)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.3333
_diffrn_reflns_number            10448
_diffrn_reflns_av_unetI/netI     0.0478
_diffrn_reflns_av_R_equivalents  0.0542
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -3
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         1.756
_diffrn_reflns_theta_max         26.337
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2941
_reflns_number_gt                2484
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.950
_reflns_Friedel_fraction_max     1.000
_reflns_Friedel_fraction_full    1.000

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0379P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   -1.7(17)
_chemical_absolute_configuration RM
_refine_ls_number_reflns         2941
_refine_ls_number_parameters     211
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0510
_refine_ls_R_factor_gt           0.0375
_refine_ls_wR_factor_ref         0.0802
_refine_ls_wR_factor_gt          0.0747
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.034
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.85729(14) 1.2185(5) 0.62935(10) 0.0281(6) Uani 1 1 d . . . . .
O2 O 1.15204(13) 1.2421(5) 0.47904(9) 0.0216(5) Uani 1 1 d . . . . .
O3 O 1.17221(12) 1.0118(5) 0.39226(9) 0.0209(5) Uani 1 1 d . . . . .
N1 N 1.02950(15) 0.6371(5) 0.36250(10) 0.0150(5) Uani 1 1 d . . . . .
H5 H 1.0859 0.7082 0.3562 0.018 Uiso 1 1 calc R U . . .
C1 C 0.7812(2) 1.0168(8) 0.61799(14) 0.0298(8) Uani 1 1 d . . . . .
H3 H 0.7530 1.0706 0.5809 0.045 Uiso 1 1 calc R U . . .
H1 H 0.7347 1.0374 0.6486 0.045 Uiso 1 1 calc R U . . .
H15 H 0.8036 0.8039 0.6167 0.045 Uiso 1 1 calc R U . . .
C2 C 0.9297(2) 1.2156(7) 0.59033(14) 0.0217(7) Uani 1 1 d . . . . .
C3 C 0.9268(2) 1.0583(7) 0.53834(13) 0.0191(7) Uani 1 1 d . . . . .
H4 H 0.8736 0.9421 0.5276 0.023 Uiso 1 1 calc R U . . .
C4 C 1.00477(19) 1.0757(6) 0.50196(13) 0.0172(6) Uani 1 1 d . . . . .
C5 C 1.02996(19) 0.9439(7) 0.44687(12) 0.0151(6) Uani 1 1 d . . . . .
C6 C 0.98403(18) 0.7400(7) 0.41029(12) 0.0147(6) Uani 1 1 d . . . . .
C7 C 0.9940(2) 0.4304(6) 0.32324(12) 0.0146(6) Uani 1 1 d . . . . .
C8 C 1.04851(19) 0.3318(6) 0.27636(13) 0.0162(6) Uani 1 1 d . . . . .
C9 C 1.0085(2) 0.1257(7) 0.23825(13) 0.0201(7) Uani 1 1 d . . . . .
H12 H 1.0437 0.0575 0.2060 0.024 Uiso 1 1 calc R U . . .
C10 C 0.9179(2) 0.0142(7) 0.24564(13) 0.0213(7) Uani 1 1 d . . . . .
H2 H 0.8927 -0.1282 0.2188 0.026 Uiso 1 1 calc R U . . .
C11 C 1.08035(19) 1.2496(7) 0.51968(13) 0.0195(7) Uani 1 1 d . . . . .
C12 C 1.12146(19) 1.0544(6) 0.43422(13) 0.0180(7) Uani 1 1 d . . . . .
C13 C 1.1464(2) 0.4482(7) 0.26875(13) 0.0207(7) Uani 1 1 d . . . . .
H6 H 1.1743 0.3520 0.2346 0.031 Uiso 1 1 calc R U . . .
H7 H 1.1833 0.3960 0.3029 0.031 Uiso 1 1 calc R U . . .
H8 H 1.1454 0.6721 0.2637 0.031 Uiso 1 1 calc R U . . .
C14 C 0.8657(2) 0.1107(7) 0.29172(13) 0.0191(7) Uani 1 1 d . . . . .
H9 H 0.8041 0.0359 0.2966 0.023 Uiso 1 1 calc R U . . .
C15 C 0.90296(19) 0.3193(6) 0.33151(12) 0.0164(6) Uani 1 1 d . . . . .
C16 C 0.85295(18) 0.4288(7) 0.38079(12) 0.0178(6) Uani 1 1 d . . . . .
H10 H 0.7912 0.3590 0.3871 0.021 Uiso 1 1 calc R U . . .
C17 C 0.89094(19) 0.6273(7) 0.41830(13) 0.0166(6) Uani 1 1 d . . . . .
H11 H 0.8558 0.6943 0.4506 0.020 Uiso 1 1 calc R U . . .
C18 C 1.0844(2) 1.4051(7) 0.57116(14) 0.0247(7) Uani 1 1 d . . . . .
H13 H 1.1379 1.5197 0.5819 0.030 Uiso 1 1 calc R U . . .
C19 C 1.0073(2) 1.3878(7) 0.60662(13) 0.0257(8) Uani 1 1 d . . . . .
H14 H 1.0071 1.4941 0.6424 0.031 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C2 1.380(4) . ?
O1 C1 1.427(4) . ?
O2 C12 1.392(4) . ?
O2 C11 1.398(3) . ?
O3 C12 1.231(3) . ?
N1 C6 1.363(3) . ?
N1 C7 1.378(4) . ?
N1 H5 0.8800 . ?
C1 H3 0.9800 . ?
C1 H1 0.9800 . ?
C1 H15 0.9800 . ?
C2 C3 1.387(4) . ?
C2 C19 1.396(5) . ?
C3 C4 1.406(4) . ?
C3 H4 0.9500 . ?
C4 C11 1.386(4) . ?
C4 C5 1.446(4) . ?
C5 C6 1.393(4) . ?
C5 C12 1.431(4) . ?
C6 C17 1.438(4) . ?
C7 C8 1.408(4) . ?
C7 C15 1.408(4) . ?
C8 C9 1.384(4) . ?
C8 C13 1.507(4) . ?
C9 C10 1.401(4) . ?
C9 H12 0.9500 . ?
C10 C14 1.373(4) . ?
C10 H2 0.9500 . ?
C11 C18 1.373(4) . ?
C13 H6 0.9800 . ?
C13 H7 0.9800 . ?
C13 H8 0.9800 . ?
C14 C15 1.400(4) . ?
C14 H9 0.9500 . ?
C15 C16 1.432(4) . ?
C16 C17 1.341(4) . ?
C16 H10 0.9500 . ?
C17 H11 0.9500 . ?
C18 C19 1.383(5) . ?
C18 H13 0.9500 . ?
C19 H14 0.9500 . ?

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
C2 O1 C1 116.9(2) . . ?
C12 O2 C11 106.5(2) . . ?
C6 N1 C7 125.0(2) . . ?
C6 N1 H5 117.5 . . ?
C7 N1 H5 117.5 . . ?
O1 C1 H3 109.5 . . ?
O1 C1 H1 109.5 . . ?
H3 C1 H1 109.5 . . ?
O1 C1 H15 109.5 . . ?
H3 C1 H15 109.5 . . ?
H1 C1 H15 109.5 . . ?
O1 C2 C3 123.5(3) . . ?
O1 C2 C19 114.9(3) . . ?
C3 C2 C19 121.6(3) . . ?
C2 C3 C4 118.1(3) . . ?
C2 C3 H4 120.9 . . ?
C4 C3 H4 120.9 . . ?
C11 C4 C3 118.5(3) . . ?
C11 C4 C5 106.3(2) . . ?
C3 C4 C5 135.2(3) . . ?
C6 C5 C12 121.6(2) . . ?
C6 C5 C4 132.1(3) . . ?
C12 C5 C4 106.2(2) . . ?
N1 C6 C5 118.5(2) . . ?
N1 C6 C17 116.1(2) . . ?
C5 C6 C17 125.4(3) . . ?
N1 C7 C8 120.1(3) . . ?
N1 C7 C15 118.6(2) . . ?
C8 C7 C15 121.3(3) . . ?
C9 C8 C7 117.3(3) . . ?
C9 C8 C13 122.1(3) . . ?
C7 C8 C13 120.6(3) . . ?
C8 C9 C10 122.2(3) . . ?
C8 C9 H12 118.9 . . ?
C10 C9 H12 118.9 . . ?
C14 C10 C9 119.9(3) . . ?
C14 C10 H2 120.0 . . ?
C9 C10 H2 120.0 . . ?
C18 C11 C4 124.0(3) . . ?
C18 C11 O2 124.5(3) . . ?
C4 C11 O2 111.5(2) . . ?
O3 C12 O2 119.4(2) . . ?
O3 C12 C5 131.1(3) . . ?
O2 C12 C5 109.5(2) . . ?
C8 C13 H6 109.5 . . ?
C8 C13 H7 109.5 . . ?
H6 C13 H7 109.5 . . ?
C8 C13 H8 109.5 . . ?
H6 C13 H8 109.5 . . ?
H7 C13 H8 109.5 . . ?
C10 C14 C15 120.1(3) . . ?
C10 C14 H9 119.9 . . ?
C15 C14 H9 119.9 . . ?
C14 C15 C7 119.2(3) . . ?
C14 C15 C16 123.3(3) . . ?
C7 C15 C16 117.5(3) . . ?
C17 C16 C15 121.8(3) . . ?
C17 C16 H10 119.1 . . ?
C15 C16 H10 119.1 . . ?
C16 C17 C6 121.0(3) . . ?
C16 C17 H11 119.5 . . ?
C6 C17 H11 119.5 . . ?
C11 C18 C19 117.2(3) . . ?
C11 C18 H13 121.4 . . ?
C19 C18 H13 121.4 . . ?
C18 C19 C2 120.6(3) . . ?
C18 C19 H14 119.7 . . ?
C2 C19 H14 119.7 . . ?

_refine_diff_density_max         0.147
_refine_diff_density_min         -0.211
_refine_diff_density_rms         0.041

_shelxl_version_number           2014/6



####################################################################### 
# 
# 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_d19251
_database_code_depnum_ccdc_archive 'CCDC 1829191'
_audit_update_record             
;
2018-03-13 deposited with the CCDC.
2018-12-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H15 N O2'
_chemical_formula_sum            'C19 H15 N O2'
_chemical_formula_weight         289.32

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P c'

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

_cell_length_a                   21.0827(15)
_cell_length_b                   8.2829(6)
_cell_length_c                   8.2169(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.222(2)
_cell_angle_gamma                90.00
_cell_volume                     1428.93(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    6280
_cell_measurement_theta_min      2.645
_cell_measurement_theta_max      24.599

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.79
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.345
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             608
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9341
_exptl_absorpt_correction_T_max  0.9965
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'D8 Venture'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            16223
_diffrn_reflns_av_R_equivalents  0.0851
_diffrn_reflns_av_sigmaI/netI    0.0823
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.46
_diffrn_reflns_theta_max         25.06
_reflns_number_total             4764
_reflns_number_gt                3974
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SIR92 (Giacovazzo et al, 1993)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0399P)²+0.2051P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.052(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.3(12)
_refine_ls_number_reflns         4764
_refine_ls_number_parameters     398
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0603
_refine_ls_R_factor_gt           0.0448
_refine_ls_wR_factor_ref         0.1156
_refine_ls_wR_factor_gt          0.1034
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_restrained_S_all      1.012
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.26476(14) 0.1027(3) 0.5570(3) 0.0343(6) Uani 1 1 d . . .
C2 C 0.30240(16) -0.0120(4) 0.6685(3) 0.0402(7) Uani 1 1 d . . .
H2A H 0.2731 -0.0923 0.7102 0.048 Uiso 1 1 calc R . .
H2B H 0.3329 -0.0709 0.6055 0.048 Uiso 1 1 calc R . .
C3 C 0.37499(14) 0.1901(4) 0.7562(3) 0.0373(7) Uani 1 1 d . . .
C4 C 0.43318(15) 0.2124(4) 0.8454(4) 0.0460(8) Uani 1 1 d . . .
H4 H 0.4454 0.1455 0.9368 0.055 Uiso 1 1 calc R . .
C5 C 0.47362(15) 0.3337(4) 0.8001(4) 0.0483(8) Uani 1 1 d . . .
H5 H 0.5135 0.3506 0.8613 0.058 Uiso 1 1 calc R . .
C6 C 0.45583(14) 0.4295(4) 0.6665(4) 0.0462(8) Uani 1 1 d . . .
H6 H 0.4836 0.5116 0.6347 0.055 Uiso 1 1 calc R . .
C7 C 0.39702(13) 0.4055(4) 0.5785(3) 0.0386(7) Uani 1 1 d . . .
H7 H 0.3859 0.4695 0.4843 0.046 Uiso 1 1 calc R . .
C8 C 0.35356(13) 0.2893(3) 0.6247(3) 0.0329(6) Uani 1 1 d . . .
C9 C 0.28955(13) 0.2602(3) 0.5418(3) 0.0317(6) Uani 1 1 d . . .
C10 C 0.25181(12) 0.3831(3) 0.4625(3) 0.0310(6) Uani 1 1 d . . .
C11 C 0.26256(14) 0.5528(3) 0.4779(3) 0.0355(6) Uani 1 1 d . . .
H11 H 0.2995 0.5910 0.5411 0.043 Uiso 1 1 calc R . .
C12 C 0.22104(14) 0.6600(4) 0.4042(3) 0.0365(7) Uani 1 1 d . . .
H12 H 0.2292 0.7722 0.4179 0.044 Uiso 1 1 calc R . .
C13 C 0.16556(13) 0.6091(4) 0.3069(3) 0.0343(7) Uani 1 1 d . . .
C14 C 0.15453(13) 0.4432(3) 0.2908(3) 0.0322(6) Uani 1 1 d . . .
C15 C 0.10090(13) 0.3801(4) 0.1956(3) 0.0379(7) Uani 1 1 d . . .
C16 C 0.09203(14) 0.2025(4) 0.1743(4) 0.0480(8) Uani 1 1 d . . .
C17 C 0.05924(15) 0.4928(4) 0.1198(4) 0.0485(8) Uani 1 1 d . . .
H17 H 0.0228 0.4552 0.0542 0.058 Uiso 1 1 calc R . .
C18 C 0.06874(15) 0.6589(4) 0.1361(4) 0.0487(8) Uani 1 1 d . . .
H18 H 0.0386 0.7316 0.0837 0.058 Uiso 1 1 calc R . .
C19 C 0.12117(15) 0.7176(4) 0.2271(3) 0.0425(7) Uani 1 1 d . . .
H19 H 0.1278 0.8308 0.2367 0.051 Uiso 1 1 calc R . .
C20 C 0.73511(14) 0.6044(3) 0.6664(3) 0.0338(6) Uani 1 1 d . . .
C21 C 0.69690(16) 0.4888(4) 0.7611(3) 0.0404(7) Uani 1 1 d . . .
H21A H 0.6662 0.4307 0.6838 0.049 Uiso 1 1 calc R . .
H21B H 0.7260 0.4079 0.8161 0.049 Uiso 1 1 calc R . .
C22 C 0.62450(13) 0.6915(3) 0.8146(3) 0.0355(7) Uani 1 1 d . . .
C23 C 0.56601(14) 0.7130(4) 0.8767(4) 0.0453(8) Uani 1 1 d . . .
H23 H 0.5538 0.6459 0.9622 0.054 Uiso 1 1 calc R . .
C24 C 0.52575(14) 0.8338(4) 0.8122(4) 0.0487(8) Uani 1 1 d . . .
H24 H 0.4858 0.8509 0.8542 0.058 Uiso 1 1 calc R . .
C25 C 0.54379(14) 0.9287(4) 0.6872(4) 0.0447(8) Uani 1 1 d . . .
H25 H 0.5159 1.0104 0.6421 0.054 Uiso 1 1 calc R . .
C26 C 0.60264(13) 0.9062(4) 0.6262(3) 0.0392(7) Uani 1 1 d . . .
H26 H 0.6138 0.9705 0.5374 0.047 Uiso 1 1 calc R . .
C27 C 0.64555(13) 0.7902(3) 0.6938(3) 0.0333(6) Uani 1 1 d . . .
C28 C 0.71006(13) 0.7612(3) 0.6410(3) 0.0309(6) Uani 1 1 d . . .
C29 C 0.74806(12) 0.8841(3) 0.5788(3) 0.0303(6) Uani 1 1 d . . .
C30 C 0.73704(13) 1.0543(3) 0.5894(3) 0.0350(7) Uani 1 1 d . . .
H30 H 0.7000 1.0922 0.6352 0.042 Uiso 1 1 calc R . .
C31 C 0.77841(13) 1.1617(4) 0.5352(3) 0.0368(7) Uani 1 1 d . . .
H31 H 0.7702 1.2739 0.5447 0.044 Uiso 1 1 calc R . .
C32 C 0.83436(13) 1.1102(4) 0.4637(3) 0.0333(6) Uani 1 1 d . . .
C33 C 0.84531(13) 0.9447(3) 0.4538(3) 0.0324(6) Uani 1 1 d . . .
C34 C 0.89934(13) 0.8820(4) 0.3844(3) 0.0364(7) Uani 1 1 d . . .
C35 C 0.90839(14) 0.7041(4) 0.3694(4) 0.0460(8) Uani 1 1 d . . .
C36 C 0.94106(14) 0.9941(4) 0.3288(4) 0.0448(8) Uani 1 1 d . . .
H36 H 0.9777 0.9561 0.2811 0.054 Uiso 1 1 calc R . .
C37 C 0.93171(15) 1.1592(4) 0.3398(4) 0.0477(8) Uani 1 1 d . . .
H37 H 0.9620 1.2318 0.3020 0.057 Uiso 1 1 calc R . .
C38 C 0.87851(14) 1.2183(4) 0.4053(4) 0.0429(8) Uani 1 1 d . . .
H38 H 0.8717 1.3314 0.4111 0.051 Uiso 1 1 calc R . .
N1 N 0.19780(10) 0.3388(3) 0.3705(3) 0.0313(5) Uani 1 1 d . . .
H1 H 0.1898 0.2348 0.3610 0.038 Uiso 1 1 calc R . .
N2 N 0.80212(10) 0.8397(3) 0.5127(2) 0.0315(5) Uani 1 1 d . . .
H2 H 0.8102 0.7358 0.5070 0.038 Uiso 1 1 calc R . .
O1 O 0.21303(10) 0.0512(2) 0.4827(2) 0.0398(5) Uani 1 1 d . . .
O2 O 0.33690(10) 0.0673(2) 0.8045(2) 0.0425(5) Uani 1 1 d . . .
O3 O 0.78673(9) 0.5522(2) 0.6177(2) 0.0389(5) Uani 1 1 d . . .
O4 O 0.66296(10) 0.5680(2) 0.8809(2) 0.0418(5) Uani 1 1 d . . .
H16A H 0.0507 0.1857 0.1072 0.050 Uiso 1 1 d R . .
H16B H 0.0869 0.1495 0.2726 0.050 Uiso 1 1 d R . .
H16C H 0.1249 0.1524 0.1207 0.050 Uiso 1 1 d R . .
H35A H 0.8687 0.6592 0.2965 0.050 Uiso 1 1 d R . .
H35B H 0.9110 0.6433 0.4709 0.050 Uiso 1 1 d R . .
H35C H 0.9467 0.6863 0.3051 0.050 Uiso 1 1 d 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
C1 O1 1.274(3) . ?
C1 C9 1.415(4) . ?
C1 C2 1.496(4) . ?
C2 O2 1.436(4) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 O2 1.377(4) . ?
C3 C4 1.383(4) . ?
C3 C8 1.399(4) . ?
C4 C5 1.390(5) . ?
C4 H4 0.9500 . ?
C5 C6 1.378(5) . ?
C5 H5 0.9500 . ?
C6 C7 1.392(4) . ?
C6 H6 0.9500 . ?
C7 C8 1.405(4) . ?
C7 H7 0.9500 . ?
C8 C9 1.475(4) . ?
C9 C10 1.414(4) . ?
C10 N1 1.358(3) . ?
C10 C11 1.428(4) . ?
C11 C12 1.350(4) . ?
C11 H11 0.9500 . ?
C12 C13 1.419(4) . ?
C12 H12 0.9500 . ?
C13 C14 1.398(4) . ?
C13 C19 1.415(4) . ?
C14 N1 1.378(3) . ?
C14 C15 1.415(4) . ?
C15 C17 1.389(4) . ?
C15 C16 1.491(4) . ?
C16 H16A 0.9984 . ?
C16 H16B 0.9343 . ?
C16 H16C 0.9491 . ?
C17 C18 1.395(5) . ?
C17 H17 0.9500 . ?
C18 C19 1.366(4) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C20 O3 1.269(3) . ?
C20 C28 1.411(4) . ?
C20 C21 1.511(4) . ?
C21 O4 1.428(3) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 O4 1.386(3) . ?
C22 C23 1.388(4) . ?
C22 C27 1.390(4) . ?
C23 C24 1.385(5) . ?
C23 H23 0.9500 . ?
C24 C25 1.374(5) . ?
C24 H24 0.9500 . ?
C25 C26 1.393(4) . ?
C25 H25 0.9500 . ?
C26 C27 1.400(4) . ?
C26 H26 0.9500 . ?
C27 C28 1.485(4) . ?
C28 C29 1.419(4) . ?
C29 N2 1.357(3) . ?
C29 C30 1.433(4) . ?
C30 C31 1.350(4) . ?
C30 H30 0.9500 . ?
C31 C32 1.430(4) . ?
C31 H31 0.9500 . ?
C32 C33 1.394(4) . ?
C32 C38 1.407(4) . ?
C33 N2 1.378(3) . ?
C33 C34 1.418(4) . ?
C34 C36 1.384(4) . ?
C34 C35 1.492(4) . ?
C35 H35A 1.0528 . ?
C35 H35B 0.9714 . ?
C35 H35C 1.0150 . ?
C36 C37 1.386(5) . ?
C36 H36 0.9500 . ?
C37 C38 1.378(5) . ?
C37 H37 0.9500 . ?
C38 H38 0.9500 . ?
N1 H1 0.8800 . ?
N2 H2 0.8800 . ?

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
O1 C1 C9 125.0(3) . . ?
O1 C1 C2 117.7(3) . . ?
C9 C1 C2 117.4(3) . . ?
O2 C2 C1 112.9(2) . . ?
O2 C2 H2A 109.0 . . ?
C1 C2 H2A 109.0 . . ?
O2 C2 H2B 109.0 . . ?
C1 C2 H2B 109.0 . . ?
H2A C2 H2B 107.8 . . ?
O2 C3 C4 117.3(3) . . ?
O2 C3 C8 120.1(3) . . ?
C4 C3 C8 122.7(3) . . ?
C3 C4 C5 119.4(3) . . ?
C3 C4 H4 120.3 . . ?
C5 C4 H4 120.3 . . ?
C6 C5 C4 120.0(3) . . ?
C6 C5 H5 120.0 . . ?
C4 C5 H5 120.0 . . ?
C5 C6 C7 119.8(3) . . ?
C5 C6 H6 120.1 . . ?
C7 C6 H6 120.1 . . ?
C6 C7 C8 122.0(3) . . ?
C6 C7 H7 119.0 . . ?
C8 C7 H7 119.0 . . ?
C3 C8 C7 116.0(3) . . ?
C3 C8 C9 118.6(2) . . ?
C7 C8 C9 125.4(3) . . ?
C10 C9 C1 120.5(2) . . ?
C10 C9 C8 123.2(3) . . ?
C1 C9 C8 116.1(2) . . ?
N1 C10 C9 118.1(2) . . ?
N1 C10 C11 115.7(2) . . ?
C9 C10 C11 126.1(3) . . ?
C12 C11 C10 121.0(3) . . ?
C12 C11 H11 119.5 . . ?
C10 C11 H11 119.5 . . ?
C11 C12 C13 121.7(3) . . ?
C11 C12 H12 119.2 . . ?
C13 C12 H12 119.2 . . ?
C14 C13 C19 118.9(3) . . ?
C14 C13 C12 117.8(3) . . ?
C19 C13 C12 123.3(3) . . ?
N1 C14 C13 118.3(2) . . ?
N1 C14 C15 119.5(2) . . ?
C13 C14 C15 122.2(3) . . ?
C17 C15 C14 116.1(3) . . ?
C17 C15 C16 122.9(3) . . ?
C14 C15 C16 121.0(3) . . ?
C15 C16 H16A 107.2 . . ?
C15 C16 H16B 112.7 . . ?
H16A C16 H16B 104.3 . . ?
C15 C16 H16C 113.4 . . ?
H16A C16 H16C 108.7 . . ?
H16B C16 H16C 110.1 . . ?
C15 C17 C18 122.7(3) . . ?
C15 C17 H17 118.7 . . ?
C18 C17 H17 118.7 . . ?
C19 C18 C17 120.4(3) . . ?
C19 C18 H18 119.8 . . ?
C17 C18 H18 119.8 . . ?
C18 C19 C13 119.7(3) . . ?
C18 C19 H19 120.1 . . ?
C13 C19 H19 120.1 . . ?
O3 C20 C28 125.9(3) . . ?
O3 C20 C21 117.4(2) . . ?
C28 C20 C21 116.7(3) . . ?
O4 C21 C20 112.8(2) . . ?
O4 C21 H21A 109.0 . . ?
C20 C21 H21A 109.0 . . ?
O4 C21 H21B 109.0 . . ?
C20 C21 H21B 109.0 . . ?
H21A C21 H21B 107.8 . . ?
O4 C22 C23 117.3(3) . . ?
O4 C22 C27 120.1(2) . . ?
C23 C22 C27 122.6(3) . . ?
C24 C23 C22 119.1(3) . . ?
C24 C23 H23 120.5 . . ?
C22 C23 H23 120.5 . . ?
C25 C24 C23 119.8(3) . . ?
C25 C24 H24 120.1 . . ?
C23 C24 H24 120.1 . . ?
C24 C25 C26 120.6(3) . . ?
C24 C25 H25 119.7 . . ?
C26 C25 H25 119.7 . . ?
C25 C26 C27 120.9(3) . . ?
C25 C26 H26 119.6 . . ?
C27 C26 H26 119.6 . . ?
C22 C27 C26 116.8(3) . . ?
C22 C27 C28 118.3(2) . . ?
C26 C27 C28 124.8(3) . . ?
C20 C28 C29 119.9(2) . . ?
C20 C28 C27 116.5(2) . . ?
C29 C28 C27 123.5(2) . . ?
N2 C29 C28 118.2(2) . . ?
N2 C29 C30 115.9(2) . . ?
C28 C29 C30 125.8(2) . . ?
C31 C30 C29 121.0(3) . . ?
C31 C30 H30 119.5 . . ?
C29 C30 H30 119.5 . . ?
C30 C31 C32 121.4(3) . . ?
C30 C31 H31 119.3 . . ?
C32 C31 H31 119.3 . . ?
C33 C32 C38 119.2(3) . . ?
C33 C32 C31 117.7(2) . . ?
C38 C32 C31 123.1(3) . . ?
N2 C33 C32 118.8(2) . . ?
N2 C33 C34 119.4(2) . . ?
C32 C33 C34 121.8(3) . . ?
C36 C34 C33 116.4(3) . . ?
C36 C34 C35 123.0(3) . . ?
C33 C34 C35 120.5(3) . . ?
C34 C35 H35A 107.2 . . ?
C34 C35 H35B 116.1 . . ?
H35A C35 H35B 106.5 . . ?
C34 C35 H35C 107.5 . . ?
H35A C35 H35C 106.3 . . ?
H35B C35 H35C 112.7 . . ?
C34 C36 C37 122.8(3) . . ?
C34 C36 H36 118.6 . . ?
C37 C36 H36 118.6 . . ?
C38 C37 C36 120.1(3) . . ?
C38 C37 H37 119.9 . . ?
C36 C37 H37 119.9 . . ?
C37 C38 C32 119.7(3) . . ?
C37 C38 H38 120.2 . . ?
C32 C38 H38 120.2 . . ?
C10 N1 C14 125.5(2) . . ?
C10 N1 H1 117.3 . . ?
C14 N1 H1 117.3 . . ?
C29 N2 C33 125.2(2) . . ?
C29 N2 H2 117.4 . . ?
C33 N2 H2 117.4 . . ?
C3 O2 C2 112.4(2) . . ?
C22 O4 C21 112.4(2) . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        25.06
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.168
_refine_diff_density_min         -0.149
_refine_diff_density_rms         0.038
####################################################################### 
# 
# 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_170934lt_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1829192'
_audit_update_record             
;
2018-03-13 deposited with the CCDC.
2018-12-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H33 Au Cl O2 P'
_chemical_formula_weight         664.93

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'
Cl Cl 0.1484 0.1585 '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'
Au Au -2.0133 8.8022 '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'

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

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   9.2179(4)
_cell_length_b                   10.4777(5)
_cell_length_c                   14.2247(7)
_cell_angle_alpha                100.062(2)
_cell_angle_beta                 92.031(2)
_cell_angle_gamma                103.287(2)
_cell_volume                     1312.41(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9907
_cell_measurement_theta_min      2.6059
_cell_measurement_theta_max      26.3845

_exptl_crystal_description       Tabullar
_exptl_crystal_colour            Yellow
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.683
_exptl_crystal_F_000             656
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.02
_exptl_absorpt_coefficient_mu    5.790
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7527
_exptl_absorpt_correction_T_max  0.9485
_exptl_absorpt_process_details   'SADABS V2014/4 (Bruker AXS Inc.)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.3333
_diffrn_reflns_number            19696
_diffrn_reflns_av_unetI/netI     0.0181
_diffrn_reflns_av_R_equivalents  0.0197
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.458
_diffrn_reflns_theta_max         26.432
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             5361
_reflns_number_gt                5204
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0115P)²+3.5262P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5361
_refine_ls_number_parameters     304
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0196
_refine_ls_R_factor_gt           0.0186
_refine_ls_wR_factor_ref         0.0480
_refine_ls_wR_factor_gt          0.0442
_refine_ls_goodness_of_fit_ref   1.137
_refine_ls_restrained_S_all      1.137
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Au1 Au 0.31400(2) 0.54081(2) 0.69721(2) 0.01684(4) Uani 1 1 d . . . . .
C1 C 0.2097(3) 0.2113(3) 0.6056(2) 0.0178(6) Uani 1 1 d . . . . .
C2 C 0.2330(4) 0.2483(4) 0.5063(2) 0.0238(7) Uani 1 1 d . . . . .
H2A H 0.3242 0.2254 0.4829 0.036 Uiso 1 1 calc R U . . .
H2B H 0.2426 0.3444 0.5112 0.036 Uiso 1 1 calc R U . . .
H2C H 0.1471 0.1988 0.4616 0.036 Uiso 1 1 calc R U . . .
C3 C 0.0575(3) 0.2337(3) 0.6360(2) 0.0224(7) Uani 1 1 d . . . . .
H3A H -0.0224 0.1758 0.5900 0.034 Uiso 1 1 calc R U . . .
H3B H 0.0560 0.3272 0.6376 0.034 Uiso 1 1 calc R U . . .
H3C H 0.0419 0.2122 0.6998 0.034 Uiso 1 1 calc R U . . .
C4 C 0.2074(4) 0.0639(3) 0.6001(2) 0.0253(7) Uani 1 1 d . . . . .
H4A H 0.1322 0.0094 0.5496 0.038 Uiso 1 1 calc R U . . .
H4B H 0.1823 0.0383 0.6617 0.038 Uiso 1 1 calc R U . . .
H4C H 0.3060 0.0493 0.5854 0.038 Uiso 1 1 calc R U . . .
C5 C 0.5537(3) 0.3355(3) 0.6690(2) 0.0181(6) Uani 1 1 d . . . . .
C6 C 0.5907(4) 0.2010(3) 0.6323(2) 0.0242(7) Uani 1 1 d . . . . .
H6A H 0.6974 0.2156 0.6221 0.036 Uiso 1 1 calc R U . . .
H6B H 0.5316 0.1583 0.5717 0.036 Uiso 1 1 calc R U . . .
H6C H 0.5667 0.1432 0.6796 0.036 Uiso 1 1 calc R U . . .
C7 C 0.6483(4) 0.4054(4) 0.7629(2) 0.0271(7) Uani 1 1 d . . . . .
H7A H 0.6284 0.3480 0.8108 0.041 Uiso 1 1 calc R U . . .
H7B H 0.6223 0.4902 0.7865 0.041 Uiso 1 1 calc R U . . .
H7C H 0.7546 0.4224 0.7513 0.041 Uiso 1 1 calc R U . . .
C8 C 0.5959(4) 0.4232(3) 0.5930(2) 0.0231(7) Uani 1 1 d . . . . .
H8A H 0.7031 0.4368 0.5848 0.035 Uiso 1 1 calc R U . . .
H8B H 0.5722 0.5098 0.6138 0.035 Uiso 1 1 calc R U . . .
H8C H 0.5391 0.3787 0.5319 0.035 Uiso 1 1 calc R U . . .
C9 C 0.3258(3) 0.2718(3) 0.8088(2) 0.0166(6) Uani 1 1 d . . . . .
C10 C 0.3610(3) 0.1508(3) 0.8177(2) 0.0193(6) Uani 1 1 d . . . . .
H10 H 0.3978 0.1027 0.7646 0.023 Uiso 1 1 calc R U . . .
C11 C 0.3443(4) 0.0990(3) 0.9009(2) 0.0234(7) Uani 1 1 d . . . . .
H11 H 0.3696 0.0170 0.9047 0.028 Uiso 1 1 calc R U . . .
C12 C 0.2904(4) 0.1681(4) 0.9784(2) 0.0285(8) Uani 1 1 d . . . . .
H12 H 0.2776 0.1337 1.0359 0.034 Uiso 1 1 calc R U . . .
C13 C 0.2555(4) 0.2875(4) 0.9714(2) 0.0259(7) Uani 1 1 d . . . . .
H13 H 0.2190 0.3345 1.0251 0.031 Uiso 1 1 calc R U . . .
C14 C 0.2717(3) 0.3418(3) 0.8882(2) 0.0190(6) Uani 1 1 d . . . . .
C15 C 0.2301(3) 0.4726(3) 0.8930(2) 0.0200(6) Uani 1 1 d . . . . .
C16 C 0.0850(4) 0.4779(4) 0.8661(2) 0.0242(7) Uani 1 1 d . . . . .
H16 H 0.0137 0.3980 0.8382 0.029 Uiso 1 1 calc R U . . .
C17 C 0.0438(4) 0.5986(4) 0.8794(2) 0.0278(7) Uani 1 1 d . . . . .
H17 H -0.0551 0.6010 0.8600 0.033 Uiso 1 1 calc R U . . .
C18 C 0.1456(4) 0.7153(4) 0.9208(3) 0.0310(8) Uani 1 1 d . . . . .
H18 H 0.1167 0.7977 0.9305 0.037 Uiso 1 1 calc R U . . .
C19 C 0.2898(4) 0.7116(4) 0.9481(3) 0.0312(8) Uani 1 1 d . . . . .
H19 H 0.3605 0.7918 0.9762 0.037 Uiso 1 1 calc R U . . .
C20 C 0.3315(4) 0.5909(4) 0.9347(2) 0.0265(7) Uani 1 1 d . . . . .
H20 H 0.4306 0.5892 0.9541 0.032 Uiso 1 1 calc R U . . .
C21 C 0.2721(4) 0.7275(3) 0.6875(2) 0.0211(6) Uani 1 1 d . . . . .
H21 H 0.2280 0.7617 0.7472 0.025 Uiso 1 1 calc R U . . .
C22 C 0.4155(4) 0.8173(3) 0.6815(2) 0.0195(6) Uani 1 1 d . . . . .
C23 C 0.6431(4) 0.9040(3) 0.7805(2) 0.0212(6) Uani 1 1 d . . . . .
C24 C 0.7236(4) 0.8114(4) 0.7464(2) 0.0296(8) Uani 1 1 d . . . . .
H24 H 0.6737 0.7254 0.7120 0.035 Uiso 1 1 calc R U . . .
C25 C 0.8771(4) 0.8457(5) 0.7630(3) 0.0374(9) Uani 1 1 d . . . . .
H25 H 0.9338 0.7832 0.7401 0.045 Uiso 1 1 calc R U . . .
C26 C 0.9491(4) 0.9721(5) 0.8135(3) 0.0413(10) Uani 1 1 d . . . . .
H26 H 1.0548 0.9961 0.8251 0.050 Uiso 1 1 calc R U . . .
C27 C 0.8653(4) 1.0631(4) 0.8468(3) 0.0340(9) Uani 1 1 d . . . . .
H27 H 0.9142 1.1491 0.8817 0.041 Uiso 1 1 calc R U . . .
C28 C 0.7136(4) 1.0298(3) 0.8296(2) 0.0262(7) Uani 1 1 d . . . . .
H28 H 0.6568 1.0927 0.8514 0.031 Uiso 1 1 calc R U . . .
Cl1 Cl 0.14279(9) 0.71155(8) 0.58670(6) 0.02753(17) Uani 1 1 d . . . . .
O1 O 0.4864(3) 0.8669(2) 0.77269(16) 0.0247(5) Uani 1 1 d . . . . .
O2 O 0.4749(3) 0.8478(2) 0.61113(17) 0.0264(5) Uani 1 1 d . . . . .
P1 P 0.35333(8) 0.33228(8) 0.69521(5) 0.01399(15) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Au1 C21 2.105(3) . ?
Au1 P1 2.2911(8) . ?
C1 C4 1.528(4) . ?
C1 C2 1.538(4) . ?
C1 C3 1.539(4) . ?
C1 P1 1.879(3) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 C6 1.533(4) . ?
C5 C7 1.537(4) . ?
C5 C8 1.542(4) . ?
C5 P1 1.891(3) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 C10 1.403(4) . ?
C9 C14 1.408(4) . ?
C9 P1 1.841(3) . ?
C10 C11 1.386(4) . ?
C10 H10 0.9500 . ?
C11 C12 1.382(5) . ?
C11 H11 0.9500 . ?
C12 C13 1.380(5) . ?
C12 H12 0.9500 . ?
C13 C14 1.398(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.497(5) . ?
C15 C20 1.390(5) . ?
C15 C16 1.395(4) . ?
C16 C17 1.387(5) . ?
C16 H16 0.9500 . ?
C17 C18 1.380(5) . ?
C17 H17 0.9500 . ?
C18 C19 1.383(5) . ?
C18 H18 0.9500 . ?
C19 C20 1.388(5) . ?
C19 H19 0.9500 . ?
C20 H20 0.9500 . ?
C21 C22 1.450(5) . ?
C21 Cl1 1.791(3) . ?
C21 H21 1.0000 . ?
C22 O2 1.214(4) . ?
C22 O1 1.389(4) . ?
C23 C28 1.378(5) . ?
C23 C24 1.385(5) . ?
C23 O1 1.402(4) . ?
C24 C25 1.378(5) . ?
C24 H24 0.9500 . ?
C25 C26 1.392(6) . ?
C25 H25 0.9500 . ?
C26 C27 1.392(6) . ?
C26 H26 0.9500 . ?
C27 C28 1.364(5) . ?
C27 H27 0.9500 . ?
C28 H28 0.9500 . ?

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
C21 Au1 P1 175.48(9) . . ?
C4 C1 C2 109.7(3) . . ?
C4 C1 C3 108.5(3) . . ?
C2 C1 C3 108.5(3) . . ?
C4 C1 P1 115.7(2) . . ?
C2 C1 P1 108.6(2) . . ?
C3 C1 P1 105.6(2) . . ?
C1 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
C1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C1 C3 H3A 109.5 . . ?
C1 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C1 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C1 C4 H4A 109.5 . . ?
C1 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C1 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C6 C5 C7 110.1(3) . . ?
C6 C5 C8 107.3(3) . . ?
C7 C5 C8 108.3(3) . . ?
C6 C5 P1 117.1(2) . . ?
C7 C5 P1 105.7(2) . . ?
C8 C5 P1 108.0(2) . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C5 C7 H7A 109.5 . . ?
C5 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C5 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C5 C8 H8A 109.5 . . ?
C5 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C5 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C10 C9 C14 117.9(3) . . ?
C10 C9 P1 119.0(2) . . ?
C14 C9 P1 123.1(2) . . ?
C11 C10 C9 122.5(3) . . ?
C11 C10 H10 118.7 . . ?
C9 C10 H10 118.7 . . ?
C12 C11 C10 119.2(3) . . ?
C12 C11 H11 120.4 . . ?
C10 C11 H11 120.4 . . ?
C13 C12 C11 119.3(3) . . ?
C13 C12 H12 120.4 . . ?
C11 C12 H12 120.4 . . ?
C12 C13 C14 122.5(3) . . ?
C12 C13 H13 118.8 . . ?
C14 C13 H13 118.8 . . ?
C13 C14 C9 118.6(3) . . ?
C13 C14 C15 115.6(3) . . ?
C9 C14 C15 125.8(3) . . ?
C20 C15 C16 118.4(3) . . ?
C20 C15 C14 120.2(3) . . ?
C16 C15 C14 121.1(3) . . ?
C17 C16 C15 120.7(3) . . ?
C17 C16 H16 119.7 . . ?
C15 C16 H16 119.7 . . ?
C18 C17 C16 120.3(3) . . ?
C18 C17 H17 119.8 . . ?
C16 C17 H17 119.8 . . ?
C17 C18 C19 119.7(3) . . ?
C17 C18 H18 120.2 . . ?
C19 C18 H18 120.2 . . ?
C18 C19 C20 120.1(3) . . ?
C18 C19 H19 119.9 . . ?
C20 C19 H19 119.9 . . ?
C19 C20 C15 120.8(3) . . ?
C19 C20 H20 119.6 . . ?
C15 C20 H20 119.6 . . ?
C22 C21 Cl1 112.8(2) . . ?
C22 C21 Au1 106.9(2) . . ?
Cl1 C21 Au1 110.37(16) . . ?
C22 C21 H21 108.9 . . ?
Cl1 C21 H21 108.9 . . ?
Au1 C21 H21 108.9 . . ?
O2 C22 O1 121.1(3) . . ?
O2 C22 C21 129.2(3) . . ?
O1 C22 C21 109.7(3) . . ?
C28 C23 C24 121.3(3) . . ?
C28 C23 O1 118.4(3) . . ?
C24 C23 O1 120.0(3) . . ?
C25 C24 C23 119.1(4) . . ?
C25 C24 H24 120.4 . . ?
C23 C24 H24 120.4 . . ?
C24 C25 C26 119.9(4) . . ?
C24 C25 H25 120.0 . . ?
C26 C25 H25 120.0 . . ?
C27 C26 C25 119.7(3) . . ?
C27 C26 H26 120.2 . . ?
C25 C26 H26 120.2 . . ?
C28 C27 C26 120.5(4) . . ?
C28 C27 H27 119.8 . . ?
C26 C27 H27 119.8 . . ?
C27 C28 C23 119.5(3) . . ?
C27 C28 H28 120.3 . . ?
C23 C28 H28 120.3 . . ?
C22 O1 C23 117.3(2) . . ?
C9 P1 C1 105.15(14) . . ?
C9 P1 C5 106.37(13) . . ?
C1 P1 C5 114.52(14) . . ?
C9 P1 Au1 114.75(10) . . ?
C1 P1 Au1 107.44(10) . . ?
C5 P1 Au1 108.78(10) . . ?

_refine_diff_density_max         1.390
_refine_diff_density_min         -0.666
_refine_diff_density_rms         0.102

_shelxl_version_number           2014/6



