# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_JS223_a
_database_code_depnum_ccdc_archive 'CCDC 1983601'
loop_
_audit_author_name
_audit_author_address
'Manuela Weber'
;Freie Universitaet Berlin Anorganische Chemie
Germany
;
_audit_update_record             
;
2020-02-12 deposited with the CCDC.	2021-11-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H32 Au2 Cl2 N2 O4 P2 S2'
_chemical_formula_weight         1003.41

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   8.8016(5)
_cell_length_b                   9.8055(4)
_cell_length_c                   17.4622(9)
_cell_angle_alpha                90
_cell_angle_beta                 96.710(2)
_cell_angle_gamma                90
_cell_volume                     1496.74(13)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9356
_cell_measurement_theta_max      26.43
_cell_measurement_theta_min      2.35
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.226
_exptl_crystal_F_000             952
_exptl_transmission_factor_min   0.5995
_exptl_transmission_factor_max   0.7454
_exptl_crystal_colour            yellow
_exptl_crystal_description       needle
_exptl_crystal_size_max          0.115
_exptl_crystal_size_mid          0.035
_exptl_crystal_size_min          0.02
_exptl_absorpt_coefficient_mu    10.250
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_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 ?
_diffrn_reflns_number            18922
_diffrn_reflns_av_unetI/netI     0.0245
_diffrn_reflns_av_R_equivalents  0.0423
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.349
_diffrn_reflns_theta_max         26.446
_diffrn_reflns_theta_full        26.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3072
_reflns_number_gt                2653
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+14.0319P] 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         3072
_refine_ls_number_parameters     176
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0434
_refine_ls_R_factor_gt           0.0335
_refine_ls_wR_factor_ref         0.0582
_refine_ls_wR_factor_gt          0.0557
_refine_ls_goodness_of_fit_ref   1.187
_refine_ls_restrained_S_all      1.187
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Au1 Au 0.48580(3) 0.25567(2) 0.38438(2) 0.01426(7) Uani 1 1 d . . . . .
S1 S 0.26937(16) 0.62610(15) 0.40444(8) 0.0108(3) Uani 1 1 d . . . . .
P1 P 0.43420(17) 0.38076(15) 0.48288(8) 0.0096(3) Uani 1 1 d . . . . .
Cl1 Cl 0.55748(19) 0.12895(17) 0.28603(9) 0.0240(4) Uani 1 1 d . . . . .
O1 O 0.2502(5) 0.7591(5) 0.4366(2) 0.0172(9) Uani 1 1 d . . . . .
O2 O 0.1481(5) 0.5282(5) 0.3961(2) 0.0171(9) Uani 1 1 d . . . . .
N1 N 0.4056(5) 0.5514(5) 0.4634(3) 0.0092(10) Uani 1 1 d . . . . .
C8 C 0.3921(7) 0.5566(6) 0.1940(4) 0.0148(13) Uani 1 1 d . . . . .
H8 H 0.381869 0.485310 0.156871 0.018 Uiso 1 1 calc R U . . .
C2 C 0.2667(7) 0.2027(6) 0.5605(4) 0.0190(14) Uani 1 1 d . . . . .
C6 C 0.3463(6) 0.6454(6) 0.3170(3) 0.0108(12) Uani 1 1 d . . . . .
C12 C 0.5331(8) 0.6966(7) 0.1015(4) 0.0219(15) Uani 1 1 d . . . . .
H12A H 0.644237 0.707974 0.111847 0.033 Uiso 1 1 calc R U . . .
H12B H 0.488032 0.778399 0.075800 0.033 Uiso 1 1 calc R U . . .
H12C H 0.510070 0.617183 0.068042 0.033 Uiso 1 1 calc R U . . .
C7 C 0.3326(7) 0.5391(6) 0.2632(3) 0.0129(12) Uani 1 1 d . . . . .
H7 H 0.283267 0.456299 0.274030 0.015 Uiso 1 1 calc R U . . .
C10 C 0.4789(7) 0.7805(6) 0.2321(3) 0.0143(13) Uani 1 1 d . . . . .
H10 H 0.529541 0.862597 0.221352 0.017 Uiso 1 1 calc R U . . .
C11 C 0.4186(6) 0.7662(6) 0.3014(3) 0.0149(12) Uani 1 1 d . . . . .
H11 H 0.426665 0.838432 0.337918 0.018 Uiso 1 1 calc R U . . .
C9 C 0.4658(7) 0.6750(6) 0.1777(3) 0.0123(12) Uani 1 1 d . . . . .
C5 C 0.2547(7) 0.4468(6) 0.6031(4) 0.0206(14) Uani 1 1 d . . . . .
H5A H 0.299951 0.431682 0.656378 0.031 Uiso 1 1 calc R U . . .
H5B H 0.142943 0.445994 0.600687 0.031 Uiso 1 1 calc R U . . .
H5C H 0.288423 0.535258 0.585109 0.031 Uiso 1 1 calc R U . . .
C1 C 0.3064(7) 0.3327(7) 0.5512(4) 0.0177(14) Uani 1 1 d . . . . .
C4 C 0.1637(8) 0.1681(7) 0.6212(4) 0.0247(15) Uani 1 1 d . . . . .
H4A H 0.181424 0.233051 0.663942 0.037 Uiso 1 1 calc R U . . .
H4B H 0.186276 0.075531 0.640367 0.037 Uiso 1 1 calc R U . . .
H4C H 0.056568 0.173322 0.598558 0.037 Uiso 1 1 calc R U . . .
C3 C 0.3166(8) 0.0811(7) 0.5180(4) 0.0251(16) Uani 1 1 d . . . . .
H3A H 0.359780 0.111346 0.471566 0.038 Uiso 1 1 calc R U . . .
H3B H 0.228432 0.021824 0.503185 0.038 Uiso 1 1 calc R U . . .
H3C H 0.394414 0.030537 0.551318 0.038 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Au1 P1 2.2027(15) . ?
Au1 Cl1 2.2682(16) . ?
S1 O2 1.430(4) . ?
S1 O1 1.437(5) . ?
S1 N1 1.658(5) . ?
S1 C6 1.751(6) . ?
P1 N1 1.720(5) . ?
P1 N1 1.732(5) 3_666 ?
P1 C1 1.796(7) . ?
P1 P1 2.647(3) 3_666 ?
C8 C9 1.376(8) . ?
C8 C7 1.383(8) . ?
C8 H8 0.9500 . ?
C2 C1 1.337(9) . ?
C2 C3 1.497(9) . ?
C2 C4 1.512(9) . ?
C6 C11 1.387(8) . ?
C6 C7 1.399(8) . ?
C12 C9 1.534(9) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C7 H7 0.9500 . ?
C10 C11 1.384(8) . ?
C10 C9 1.400(8) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C5 C1 1.541(9) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
P1 Au1 Cl1 175.78(6) . . ?
O2 S1 O1 121.9(3) . . ?
O2 S1 N1 104.1(3) . . ?
O1 S1 N1 105.6(2) . . ?
O2 S1 C6 110.1(3) . . ?
O1 S1 C6 108.5(3) . . ?
N1 S1 C6 105.3(3) . . ?
N1 P1 N1 79.9(2) . 3_666 ?
N1 P1 C1 107.3(3) . . ?
N1 P1 C1 105.9(3) 3_666 . ?
N1 P1 Au1 115.23(17) . . ?
N1 P1 Au1 114.04(17) 3_666 . ?
C1 P1 Au1 125.1(2) . . ?
N1 P1 P1 40.11(16) . 3_666 ?
N1 P1 P1 39.76(16) 3_666 3_666 ?
C1 P1 P1 111.9(2) . 3_666 ?
Au1 P1 P1 122.93(9) . 3_666 ?
S1 N1 P1 129.2(3) . . ?
S1 N1 P1 130.6(3) . 3_666 ?
P1 N1 P1 100.1(2) . 3_666 ?
C9 C8 C7 121.4(6) . . ?
C9 C8 H8 119.3 . . ?
C7 C8 H8 119.3 . . ?
C1 C2 C3 127.1(6) . . ?
C1 C2 C4 119.1(6) . . ?
C3 C2 C4 113.8(6) . . ?
C11 C6 C7 120.7(5) . . ?
C11 C6 S1 119.8(4) . . ?
C7 C6 S1 119.6(5) . . ?
C9 C12 H12A 109.5 . . ?
C9 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C9 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C8 C7 C6 118.9(5) . . ?
C8 C7 H7 120.6 . . ?
C6 C7 H7 120.6 . . ?
C11 C10 C9 120.6(5) . . ?
C11 C10 H10 119.7 . . ?
C9 C10 H10 119.7 . . ?
C10 C11 C6 119.3(6) . . ?
C10 C11 H11 120.3 . . ?
C6 C11 H11 120.3 . . ?
C8 C9 C10 119.1(5) . . ?
C8 C9 C12 122.3(5) . . ?
C10 C9 C12 118.5(5) . . ?
C1 C5 H5A 109.5 . . ?
C1 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C1 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C2 C1 C5 121.5(6) . . ?
C2 C1 P1 121.6(5) . . ?
C5 C1 P1 116.8(5) . . ?
C2 C4 H4A 109.5 . . ?
C2 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C2 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C2 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C2 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 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
O2 S1 N1 P1 22.2(4) . . . . ?
O1 S1 N1 P1 151.7(4) . . . . ?
C6 S1 N1 P1 -93.7(4) . . . . ?
O2 S1 N1 P1 -163.2(4) . . . 3_666 ?
O1 S1 N1 P1 -33.7(4) . . . 3_666 ?
C6 S1 N1 P1 81.0(4) . . . 3_666 ?
N1 P1 N1 S1 175.9(5) 3_666 . . . ?
C1 P1 N1 S1 -80.5(4) . . . . ?
Au1 P1 N1 S1 63.9(4) . . . . ?
P1 P1 N1 S1 175.9(5) 3_666 . . . ?
N1 P1 N1 P1 0.001(1) 3_666 . . 3_666 ?
C1 P1 N1 P1 103.7(3) . . . 3_666 ?
Au1 P1 N1 P1 -111.92(19) . . . 3_666 ?
O2 S1 C6 C11 154.7(4) . . . . ?
O1 S1 C6 C11 19.0(5) . . . . ?
N1 S1 C6 C11 -93.6(5) . . . . ?
O2 S1 C6 C7 -24.6(5) . . . . ?
O1 S1 C6 C7 -160.3(4) . . . . ?
N1 S1 C6 C7 87.0(5) . . . . ?
C9 C8 C7 C6 0.9(9) . . . . ?
C11 C6 C7 C8 -0.2(9) . . . . ?
S1 C6 C7 C8 179.1(4) . . . . ?
C9 C10 C11 C6 0.7(9) . . . . ?
C7 C6 C11 C10 -0.6(8) . . . . ?
S1 C6 C11 C10 -179.9(4) . . . . ?
C7 C8 C9 C10 -0.9(9) . . . . ?
C7 C8 C9 C12 179.8(6) . . . . ?
C11 C10 C9 C8 0.0(9) . . . . ?
C11 C10 C9 C12 179.3(5) . . . . ?
C3 C2 C1 C5 -175.8(6) . . . . ?
C4 C2 C1 C5 2.4(10) . . . . ?
C3 C2 C1 P1 -0.6(10) . . . . ?
C4 C2 C1 P1 177.6(5) . . . . ?
N1 P1 C1 C2 159.4(6) . . . . ?
N1 P1 C1 C2 -116.5(6) 3_666 . . . ?
Au1 P1 C1 C2 19.5(7) . . . . ?
P1 P1 C1 C2 -158.2(5) 3_666 . . . ?
N1 P1 C1 C5 -25.2(5) . . . . ?
N1 P1 C1 C5 58.9(5) 3_666 . . . ?
Au1 P1 C1 C5 -165.1(4) . . . . ?
P1 P1 C1 C5 17.2(5) 3_666 . . . ?

_refine_diff_density_max         1.832
_refine_diff_density_min         -1.617
_refine_diff_density_rms         0.157

####################################################################### 
# 
# 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_YEL115_a
_database_code_depnum_ccdc_archive 'CCDC 1983602'
loop_
_audit_author_name
_audit_author_address
'Manuela Weber'
;Freie Universitaet Berlin Anorganische Chemie
Germany
;
_audit_update_record             
;
2020-02-12 deposited with the CCDC.	2021-11-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H40 Au2 Cl2 N2 O4 P2 S2'
_chemical_formula_weight         1059.51

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'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   9.6463(2)
_cell_length_b                   17.8725(4)
_cell_length_c                   10.9159(2)
_cell_angle_alpha                90
_cell_angle_beta                 114.0878(7)
_cell_angle_gamma                90
_cell_volume                     1718.06(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    102(2)
_cell_measurement_reflns_used    9910
_cell_measurement_theta_min      2.31
_cell_measurement_theta_max      25.71
_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.048
_exptl_crystal_F_000             1016
_exptl_transmission_factor_min   0.4924
_exptl_transmission_factor_max   0.7241
_exptl_crystal_size_max          0.170
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    8.935
_shelx_estimated_absorpt_T_min   0.312
_shelx_estimated_absorpt_T_max   0.716
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      102(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker Photon CMOS Detector, D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            24932
_diffrn_reflns_av_unetI/netI     0.0236
_diffrn_reflns_av_R_equivalents  0.0452
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.313
_diffrn_reflns_theta_max         25.719
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3267
_reflns_number_gt                2929
_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 APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    Mercury
_computing_publication_material  'Microsoft Word'
_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)+(0.0152P)²+4.5054P] 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         3267
_refine_ls_number_parameters     196
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0296
_refine_ls_R_factor_gt           0.0233
_refine_ls_wR_factor_ref         0.0465
_refine_ls_wR_factor_gt          0.0451
_refine_ls_goodness_of_fit_ref   1.133
_refine_ls_restrained_S_all      1.133
_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
C1 C 0.8681(5) 0.4674(2) 0.2798(4) 0.0119(8) Uani 1 1 d . . . . .
C2 C 0.8402(5) 0.4513(2) 0.3948(4) 0.0148(9) Uani 1 1 d . . . . .
C3 C 0.8946(5) 0.3838(3) 0.4606(4) 0.0194(10) Uani 1 1 d . . . . .
H3 H 0.877019 0.372140 0.537910 0.023 Uiso 1 1 calc R U . . .
C4 C 0.9735(5) 0.3330(3) 0.4174(4) 0.0218(10) Uani 1 1 d . . . . .
C5 C 1.0013(5) 0.3503(2) 0.3060(4) 0.0181(10) Uani 1 1 d . . . . .
H5 H 1.055764 0.315659 0.276452 0.022 Uiso 1 1 calc R U . . .
C6 C 0.9517(5) 0.4175(2) 0.2356(4) 0.0157(9) Uani 1 1 d . . . . .
C7 C 0.7589(5) 0.5018(3) 0.4547(4) 0.0197(10) Uani 1 1 d . . . . .
H7A H 0.659164 0.515216 0.385612 0.030 Uiso 1 1 calc R U . . .
H7AB H 0.818927 0.547267 0.489355 0.030 Uiso 1 1 calc R U . . .
H7AC H 0.745857 0.475611 0.528221 0.030 Uiso 1 1 calc R U . . .
C8 C 1.0309(6) 0.2611(3) 0.4933(5) 0.0323(12) Uani 1 1 d . . . . .
H8A H 1.041479 0.223226 0.432760 0.048 Uiso 1 1 calc R U . . .
H8AB H 0.958628 0.243376 0.529121 0.048 Uiso 1 1 calc R U . . .
H8AC H 1.129811 0.269838 0.567530 0.048 Uiso 1 1 calc R U . . .
C9 C 0.9957(5) 0.4307(3) 0.1198(4) 0.0216(10) Uani 1 1 d . . . . .
H9A H 0.903915 0.433492 0.036159 0.032 Uiso 1 1 calc R U . . .
H9AB H 1.059657 0.389348 0.114312 0.032 Uiso 1 1 calc R U . . .
H9AC H 1.052084 0.477786 0.133704 0.032 Uiso 1 1 calc R U . . .
C10 C 0.4872(5) 0.3928(2) 0.1559(4) 0.0150(9) Uani 1 1 d . . . . .
C11 C 0.5493(6) 0.3418(3) 0.0794(5) 0.0260(11) Uani 1 1 d . . . . .
H11A H 0.539677 0.366449 -0.003905 0.039 Uiso 1 1 calc R U . . .
H11B H 0.491842 0.294879 0.058042 0.039 Uiso 1 1 calc R U . . .
H11C H 0.656551 0.331235 0.134576 0.039 Uiso 1 1 calc R U . . .
C12 C 0.4604(5) 0.3666(3) 0.2605(4) 0.0178(9) Uani 1 1 d . . . . .
C13 C 0.4000(5) 0.4079(3) 0.3477(4) 0.0228(11) Uani 1 1 d . . . . .
H13A H 0.371496 0.458763 0.313244 0.034 Uiso 1 1 calc R U . . .
H13B H 0.478314 0.410118 0.439653 0.034 Uiso 1 1 calc R U . . .
H13C H 0.310533 0.381697 0.347411 0.034 Uiso 1 1 calc R U . . .
C14 C 0.4957(7) 0.2873(3) 0.3058(6) 0.0415(15) Uani 1 1 d . . . . .
H14A H 0.425929 0.253825 0.237060 0.062 Uiso 1 1 calc R U . . .
H14B H 0.483749 0.280250 0.389995 0.062 Uiso 1 1 calc R U . . .
H14C H 0.600416 0.275686 0.319917 0.062 Uiso 1 1 calc R U . . .
Au1 Au 0.36218(2) 0.57096(2) 0.19181(2) 0.01388(6) Uani 1 1 d . . . . .
Cl1 Cl 0.26904(13) 0.65697(6) 0.29158(11) 0.0227(2) Uani 1 1 d . . . . .
N1 N 0.6153(4) 0.5142(2) 0.0753(3) 0.0124(7) Uani 1 1 d . . . . .
O1 O 0.7547(4) 0.60275(17) 0.2628(3) 0.0202(7) Uani 1 1 d . . . . .
O2 O 0.8558(3) 0.56850(17) 0.0965(3) 0.0183(6) Uani 1 1 d . . . . .
P1 P 0.45535(12) 0.48676(6) 0.09780(10) 0.0113(2) Uani 1 1 d . . . . .
S1 S 0.78364(12) 0.54735(6) 0.18232(10) 0.0132(2) 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
C1 C6 1.413(6) . ?
C1 C2 1.416(6) . ?
C1 S1 1.769(4) . ?
C2 C3 1.393(6) . ?
C2 C7 1.508(6) . ?
C3 C4 1.385(7) . ?
C3 H3 0.9500 . ?
C4 C5 1.383(6) . ?
C4 C8 1.507(6) . ?
C5 C6 1.400(6) . ?
C5 H5 0.9500 . ?
C6 C9 1.507(6) . ?
C7 H7A 0.9800 . ?
C7 H7AB 0.9800 . ?
C7 H7AC 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8AB 0.9800 . ?
C8 H8AC 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9AB 0.9800 . ?
C9 H9AC 0.9800 . ?
C10 C12 1.352(6) . ?
C10 C11 1.514(6) . ?
C10 P1 1.778(4) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C14 1.495(7) . ?
C12 C13 1.498(6) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
Au1 P1 2.2087(11) . ?
Au1 Cl1 2.2704(11) . ?
N1 S1 1.675(3) . ?
N1 P1 1.727(3) 3_665 ?
N1 P1 1.730(3) . ?
O1 S1 1.425(3) . ?
O2 S1 1.427(3) . ?
P1 P1 2.651(2) 3_665 ?

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 C1 C2 121.1(4) . . ?
C6 C1 S1 119.5(3) . . ?
C2 C1 S1 119.3(3) . . ?
C3 C2 C1 117.7(4) . . ?
C3 C2 C7 116.6(4) . . ?
C1 C2 C7 125.7(4) . . ?
C4 C3 C2 122.4(4) . . ?
C4 C3 H3 118.8 . . ?
C2 C3 H3 118.8 . . ?
C5 C4 C3 118.9(4) . . ?
C5 C4 C8 121.0(4) . . ?
C3 C4 C8 120.1(4) . . ?
C4 C5 C6 122.0(4) . . ?
C4 C5 H5 119.0 . . ?
C6 C5 H5 119.0 . . ?
C5 C6 C1 118.0(4) . . ?
C5 C6 C9 116.4(4) . . ?
C1 C6 C9 125.6(4) . . ?
C2 C7 H7A 109.5 . . ?
C2 C7 H7AB 109.5 . . ?
H7A C7 H7AB 109.5 . . ?
C2 C7 H7AC 109.5 . . ?
H7A C7 H7AC 109.5 . . ?
H7AB C7 H7AC 109.5 . . ?
C4 C8 H8A 109.5 . . ?
C4 C8 H8AB 109.5 . . ?
H8A C8 H8AB 109.5 . . ?
C4 C8 H8AC 109.5 . . ?
H8A C8 H8AC 109.5 . . ?
H8AB C8 H8AC 109.5 . . ?
C6 C9 H9A 109.5 . . ?
C6 C9 H9AB 109.5 . . ?
H9A C9 H9AB 109.5 . . ?
C6 C9 H9AC 109.5 . . ?
H9A C9 H9AC 109.5 . . ?
H9AB C9 H9AC 109.5 . . ?
C12 C10 C11 120.9(4) . . ?
C12 C10 P1 124.3(3) . . ?
C11 C10 P1 114.9(3) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C12 C14 120.7(4) . . ?
C10 C12 C13 128.7(4) . . ?
C14 C12 C13 110.6(4) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
P1 Au1 Cl1 179.13(4) . . ?
S1 N1 P1 127.2(2) . 3_665 ?
S1 N1 P1 131.9(2) . . ?
P1 N1 P1 100.13(18) 3_665 . ?
N1 P1 N1 79.87(18) 3_665 . ?
N1 P1 C10 108.36(18) 3_665 . ?
N1 P1 C10 106.51(19) . . ?
N1 P1 Au1 117.45(13) 3_665 . ?
N1 P1 Au1 115.40(13) . . ?
C10 P1 Au1 121.45(14) . . ?
N1 P1 P1 39.97(11) 3_665 3_665 ?
N1 P1 P1 39.90(11) . 3_665 ?
C10 P1 P1 112.99(15) . 3_665 ?
Au1 P1 P1 125.47(7) . 3_665 ?
O1 S1 O2 119.44(19) . . ?
O1 S1 N1 107.36(18) . . ?
O2 S1 N1 103.26(17) . . ?
O1 S1 C1 110.39(19) . . ?
O2 S1 C1 112.36(19) . . ?
N1 S1 C1 102.16(18) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 -1.7(6) . . . . ?
S1 C1 C2 C3 173.1(3) . . . . ?
C6 C1 C2 C7 177.0(4) . . . . ?
S1 C1 C2 C7 -8.2(6) . . . . ?
C1 C2 C3 C4 0.0(6) . . . . ?
C7 C2 C3 C4 -178.9(4) . . . . ?
C2 C3 C4 C5 1.0(7) . . . . ?
C2 C3 C4 C8 179.5(4) . . . . ?
C3 C4 C5 C6 -0.2(7) . . . . ?
C8 C4 C5 C6 -178.7(4) . . . . ?
C4 C5 C6 C1 -1.4(6) . . . . ?
C4 C5 C6 C9 177.4(4) . . . . ?
C2 C1 C6 C5 2.4(6) . . . . ?
S1 C1 C6 C5 -172.4(3) . . . . ?
C2 C1 C6 C9 -176.4(4) . . . . ?
S1 C1 C6 C9 8.9(6) . . . . ?
C11 C10 C12 C14 1.8(7) . . . . ?
P1 C10 C12 C14 -177.8(4) . . . . ?
C11 C10 C12 C13 180.0(4) . . . . ?
P1 C10 C12 C13 0.4(7) . . . . ?
S1 N1 P1 N1 170.2(4) . . . 3_665 ?
P1 N1 P1 N1 0.000(2) 3_665 . . 3_665 ?
S1 N1 P1 C10 -83.5(3) . . . . ?
P1 N1 P1 C10 106.3(2) 3_665 . . . ?
S1 N1 P1 Au1 54.5(3) . . . . ?
P1 N1 P1 Au1 -115.69(14) 3_665 . . . ?
S1 N1 P1 P1 170.2(4) . . . 3_665 ?
C12 C10 P1 N1 -141.8(4) . . . 3_665 ?
C11 C10 P1 N1 38.6(4) . . . 3_665 ?
C12 C10 P1 N1 133.6(4) . . . . ?
C11 C10 P1 N1 -46.0(4) . . . . ?
C12 C10 P1 Au1 -1.3(5) . . . . ?
C11 C10 P1 Au1 179.1(3) . . . . ?
C12 C10 P1 P1 175.6(3) . . . 3_665 ?
C11 C10 P1 P1 -4.0(4) . . . 3_665 ?
P1 N1 S1 O1 122.8(3) 3_665 . . . ?
P1 N1 S1 O1 -45.1(3) . . . . ?
P1 N1 S1 O2 -4.3(3) 3_665 . . . ?
P1 N1 S1 O2 -172.2(3) . . . . ?
P1 N1 S1 C1 -121.1(3) 3_665 . . . ?
P1 N1 S1 C1 71.0(3) . . . . ?
C6 C1 S1 O1 -158.7(3) . . . . ?
C2 C1 S1 O1 26.4(4) . . . . ?
C6 C1 S1 O2 -22.7(4) . . . . ?
C2 C1 S1 O2 162.5(3) . . . . ?
C6 C1 S1 N1 87.4(3) . . . . ?
C2 C1 S1 N1 -87.5(3) . . . . ?

_refine_diff_density_max         1.369
_refine_diff_density_min         -0.778
_refine_diff_density_rms         0.121

####################################################################### 
# 
# 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_YEL1151
_database_code_depnum_ccdc_archive 'CCDC 1983603'
loop_
_audit_author_name
_audit_author_address
'Manuela Weber'
;Freie Universitaet Berlin Anorganische Chemie
Germany
;
_audit_update_record             
;
2020-02-12 deposited with the CCDC.	2021-11-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H20 N3 O2 P S'
_chemical_formula_weight         325.36

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'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   10.6589(3)
_cell_length_b                   17.7200(4)
_cell_length_c                   8.8396(2)
_cell_angle_alpha                90
_cell_angle_beta                 102.6651(9)
_cell_angle_gamma                90
_cell_volume                     1628.96(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    104(2)
_cell_measurement_reflns_used    7390
_cell_measurement_theta_min      2.27
_cell_measurement_theta_max      26.40
_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.327
_exptl_crystal_F_000             688
_exptl_transmission_factor_min   0.8814
_exptl_transmission_factor_max   0.9420
_exptl_crystal_size_max          0.660
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.304
_shelx_estimated_absorpt_T_min   0.824
_shelx_estimated_absorpt_T_max   0.985
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      104(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker Photon CMOS Detector, D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17318
_diffrn_reflns_av_unetI/netI     0.0408
_diffrn_reflns_av_R_equivalents  0.0524
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.271
_diffrn_reflns_theta_max         26.414
_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             3335
_reflns_number_gt                2636
_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 APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    Mercury
_computing_publication_material  'Microsoft Word'
_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)+(0.0375P)²+1.1014P] 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         3335
_refine_ls_number_parameters     196
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0575
_refine_ls_R_factor_gt           0.0370
_refine_ls_wR_factor_ref         0.0896
_refine_ls_wR_factor_gt          0.0817
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.033
_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
C1 C 0.47629(18) 0.21673(11) 0.3923(2) 0.0130(4) Uani 1 1 d . . . . .
O1 O 0.27216(14) 0.44068(8) 0.19715(15) 0.0186(3) Uani 1 1 d . . . . .
C3 C 0.20527(19) 0.46350(11) 0.5079(2) 0.0138(4) Uani 1 1 d . . . . .
C5 C 0.06309(19) 0.43471(12) 0.6823(2) 0.0169(4) Uani 1 1 d . . . . .
C4 C 0.15698(19) 0.47796(11) 0.6392(2) 0.0169(4) Uani 1 1 d . . . . .
H4 H 0.190478 0.519832 0.702378 0.020 Uiso 1 1 calc R U . . .
C13 C 0.0173(2) 0.45182(13) 0.8279(2) 0.0257(5) Uani 1 1 d . . . . .
H13A H -0.076618 0.456670 0.803092 0.039 Uiso 1 1 calc R U . . .
H13B H 0.055895 0.499183 0.872894 0.039 Uiso 1 1 calc R U . . .
H13C H 0.042625 0.410745 0.902593 0.039 Uiso 1 1 calc R U . . .
C12 C -0.0024(2) 0.28556(12) 0.3688(2) 0.0220(5) Uani 1 1 d . . . . .
H12A H -0.056491 0.300938 0.269111 0.033 Uiso 1 1 calc R U . . .
H12B H -0.054907 0.258731 0.429573 0.033 Uiso 1 1 calc R U . . .
H12C H 0.066163 0.252198 0.350601 0.033 Uiso 1 1 calc R U . . .
C11 C 0.6929(2) 0.16751(13) 0.3861(3) 0.0270(5) Uani 1 1 d . . . . .
H11A H 0.677919 0.178256 0.274795 0.040 Uiso 1 1 calc R U . . .
H11B H 0.751058 0.124266 0.411002 0.040 Uiso 1 1 calc R U . . .
H11C H 0.731664 0.211728 0.444811 0.040 Uiso 1 1 calc R U . . .
C8 C 0.56463(19) 0.14918(11) 0.4292(2) 0.0159(4) Uani 1 1 d . . . . .
C7 C 0.05652(19) 0.35477(11) 0.4569(2) 0.0144(4) Uani 1 1 d . . . . .
C6 C 0.01421(19) 0.37372(11) 0.5892(2) 0.0162(4) Uani 1 1 d . . . . .
H6 H -0.050952 0.343781 0.617449 0.019 Uiso 1 1 calc R U . . .
C9 C 0.5868(2) 0.13229(12) 0.6032(2) 0.0244(5) Uani 1 1 d . . . . .
H9A H 0.504432 0.120761 0.629937 0.037 Uiso 1 1 calc R U . . .
H9AB H 0.625641 0.176404 0.662282 0.037 Uiso 1 1 calc R U . . .
H9AC H 0.644652 0.088900 0.628495 0.037 Uiso 1 1 calc R U . . .
C14 C 0.3091(2) 0.51560(11) 0.4771(2) 0.0197(5) Uani 1 1 d . . . . .
H14A H 0.382072 0.485631 0.460277 0.030 Uiso 1 1 calc R U . . .
H14B H 0.337583 0.548966 0.566485 0.030 Uiso 1 1 calc R U . . .
H14C H 0.274926 0.546012 0.384671 0.030 Uiso 1 1 calc R U . . .
C10 C 0.5026(2) 0.08094(12) 0.3368(2) 0.0236(5) Uani 1 1 d . . . . .
H10A H 0.485980 0.092446 0.225725 0.035 Uiso 1 1 calc R U . . .
H10B H 0.421318 0.069037 0.366068 0.035 Uiso 1 1 calc R U . . .
H10C H 0.560664 0.037525 0.359201 0.035 Uiso 1 1 calc R U . . .
N1 N 0.32799(15) 0.31281(9) 0.31793(17) 0.0129(3) Uani 1 1 d . . . . .
N2 N 0.43329(16) 0.33864(9) 0.42188(18) 0.0159(4) Uani 1 1 d . . . . .
C2 C 0.15283(18) 0.40102(10) 0.4167(2) 0.0116(4) Uani 1 1 d . . . . .
O2 O 0.11797(13) 0.33577(8) 0.14117(14) 0.0184(3) Uani 1 1 d . . . . .
N3 N 0.51539(16) 0.28424(9) 0.46227(18) 0.0158(4) Uani 1 1 d . . . . .
P1 P 0.32841(5) 0.21998(3) 0.26748(6) 0.01615(14) Uani 1 1 d . . . . .
S1 S 0.21049(5) 0.37785(3) 0.25009(5) 0.01325(13) 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
C1 N3 1.369(2) . ?
C1 C8 1.514(3) . ?
C1 P1 1.715(2) . ?
O1 S1 1.4232(14) . ?
C3 C4 1.393(3) . ?
C3 C2 1.411(3) . ?
C3 C14 1.511(3) . ?
C5 C4 1.379(3) . ?
C5 C6 1.389(3) . ?
C5 C13 1.505(3) . ?
C4 H4 0.9500 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C12 C7 1.513(3) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C11 C8 1.532(3) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C8 C10 1.526(3) . ?
C8 C9 1.533(3) . ?
C7 C6 1.384(3) . ?
C7 C2 1.418(3) . ?
C6 H6 0.9500 . ?
C9 H9A 0.9800 . ?
C9 H9AB 0.9800 . ?
C9 H9AC 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
N1 N2 1.364(2) . ?
N1 P1 1.7047(16) . ?
N1 S1 1.7108(16) . ?
N2 N3 1.298(2) . ?
C2 S1 1.7638(18) . ?
O2 S1 1.4280(14) . ?

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
N3 C1 C8 118.70(16) . . ?
N3 C1 P1 114.01(14) . . ?
C8 C1 P1 127.28(14) . . ?
C4 C3 C2 116.63(18) . . ?
C4 C3 C14 117.18(17) . . ?
C2 C3 C14 126.19(17) . . ?
C4 C5 C6 118.01(18) . . ?
C4 C5 C13 121.05(19) . . ?
C6 C5 C13 120.92(19) . . ?
C5 C4 C3 123.45(19) . . ?
C5 C4 H4 118.3 . . ?
C3 C4 H4 118.3 . . ?
C5 C13 H13A 109.5 . . ?
C5 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C5 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C7 C12 H12A 109.5 . . ?
C7 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C7 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C8 C11 H11A 109.5 . . ?
C8 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C8 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C1 C8 C10 109.58(16) . . ?
C1 C8 C11 108.99(17) . . ?
C10 C8 C11 109.88(17) . . ?
C1 C8 C9 108.82(16) . . ?
C10 C8 C9 109.62(17) . . ?
C11 C8 C9 109.94(18) . . ?
C6 C7 C2 117.36(18) . . ?
C6 C7 C12 117.15(18) . . ?
C2 C7 C12 125.48(17) . . ?
C7 C6 C5 122.70(19) . . ?
C7 C6 H6 118.7 . . ?
C5 C6 H6 118.7 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9AB 109.5 . . ?
H9A C9 H9AB 109.5 . . ?
C8 C9 H9AC 109.5 . . ?
H9A C9 H9AC 109.5 . . ?
H9AB C9 H9AC 109.5 . . ?
C3 C14 H14A 109.5 . . ?
C3 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C3 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N2 N1 P1 116.81(12) . . ?
N2 N1 S1 116.17(12) . . ?
P1 N1 S1 127.02(10) . . ?
N3 N2 N1 109.97(15) . . ?
C3 C2 C7 121.85(17) . . ?
C3 C2 S1 119.53(14) . . ?
C7 C2 S1 118.60(14) . . ?
N2 N3 C1 113.86(16) . . ?
N1 P1 C1 85.35(9) . . ?
O1 S1 O2 119.16(8) . . ?
O1 S1 N1 106.67(8) . . ?
O2 S1 N1 103.22(8) . . ?
O1 S1 C2 111.29(9) . . ?
O2 S1 C2 111.64(9) . . ?
N1 S1 C2 103.09(8) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C5 C4 C3 -0.2(3) . . . . ?
C13 C5 C4 C3 178.29(18) . . . . ?
C2 C3 C4 C5 0.2(3) . . . . ?
C14 C3 C4 C5 -179.38(18) . . . . ?
N3 C1 C8 C10 -179.13(17) . . . . ?
P1 C1 C8 C10 0.0(2) . . . . ?
N3 C1 C8 C11 -58.9(2) . . . . ?
P1 C1 C8 C11 120.31(18) . . . . ?
N3 C1 C8 C9 61.0(2) . . . . ?
P1 C1 C8 C9 -119.81(18) . . . . ?
C2 C7 C6 C5 -0.7(3) . . . . ?
C12 C7 C6 C5 178.28(18) . . . . ?
C4 C5 C6 C7 0.4(3) . . . . ?
C13 C5 C6 C7 -178.05(18) . . . . ?
P1 N1 N2 N3 0.0(2) . . . . ?
S1 N1 N2 N3 -179.13(12) . . . . ?
C4 C3 C2 C7 -0.5(3) . . . . ?
C14 C3 C2 C7 179.07(18) . . . . ?
C4 C3 C2 S1 -178.98(14) . . . . ?
C14 C3 C2 S1 0.6(3) . . . . ?
C6 C7 C2 C3 0.7(3) . . . . ?
C12 C7 C2 C3 -178.16(18) . . . . ?
C6 C7 C2 S1 179.22(14) . . . . ?
C12 C7 C2 S1 0.3(3) . . . . ?
N1 N2 N3 C1 -0.1(2) . . . . ?
C8 C1 N3 N2 179.46(16) . . . . ?
P1 C1 N3 N2 0.2(2) . . . . ?
N2 N1 P1 C1 0.12(14) . . . . ?
S1 N1 P1 C1 179.08(13) . . . . ?
N3 C1 P1 N1 -0.16(14) . . . . ?
C8 C1 P1 N1 -179.36(17) . . . . ?
N2 N1 S1 O1 51.22(15) . . . . ?
P1 N1 S1 O1 -127.75(12) . . . . ?
N2 N1 S1 O2 177.58(13) . . . . ?
P1 N1 S1 O2 -1.39(14) . . . . ?
N2 N1 S1 C2 -66.08(15) . . . . ?
P1 N1 S1 C2 114.95(12) . . . . ?
C3 C2 S1 O1 -20.70(18) . . . . ?
C7 C2 S1 O1 160.77(14) . . . . ?
C3 C2 S1 O2 -156.52(14) . . . . ?
C7 C2 S1 O2 24.94(17) . . . . ?
C3 C2 S1 N1 93.30(16) . . . . ?
C7 C2 S1 N1 -85.24(16) . . . . ?

_refine_diff_density_max         0.292
_refine_diff_density_min         -0.408
_refine_diff_density_rms         0.065

