# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2020

####################################################################### 
# 
# 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_cu_4492f
_database_code_depnum_ccdc_archive 'CCDC 2001006'
loop_
_audit_author_name
_audit_author_address
'Gregor Schnakenburg'
;University of Bonn
Germany
;
_audit_update_record             
;
2020-05-04 deposited with the CCDC.	2020-09-04 downloaded from the CCDC.
;
_audit_creation_date             2016-03-01
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.21 svn.r3230 for OlexSys, GUI svn.r5103)
;
_chemical_name_common            ?
_chemical_name_systematic        AG5-3
_chemical_formula_moiety         'C27 H20 P2 S3'
_chemical_formula_sum            'C27 H20 P2 S3'
_chemical_formula_weight         502.55
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.7418(4)
_cell_length_b                   11.1986(4)
_cell_length_c                   11.7876(5)
_cell_angle_alpha                62.450(2)
_cell_angle_beta                 75.279(2)
_cell_angle_gamma                88.851(2)
_cell_volume                     1208.03(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9708
_cell_measurement_temperature    123
_cell_measurement_theta_max      72.10
_cell_measurement_theta_min      4.28
_shelx_estimated_absorpt_T_max   0.594
_shelx_estimated_absorpt_T_min   0.435
_exptl_absorpt_coefficient_mu    4.157
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.3748
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1690 before and 0.1004 after correction.
The Ratio of minimum to maximum transmission is 0.4973.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.382
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.14
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0740
_diffrn_reflns_av_unetI/netI     0.0389
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            33203
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         67.738
_diffrn_reflns_theta_min         4.283
_diffrn_ambient_temperature      123
_diffrn_detector                 'Bruker Photon100 detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CMOS area detector'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8-Venture'
_diffrn_measurement_method       'fine slicing ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3945
_reflns_number_total             4367
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_refine_diff_density_max         0.394
_refine_diff_density_min         -0.505
_refine_diff_density_rms         0.088
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     289
_refine_ls_number_reflns         4367
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0452
_refine_ls_R_factor_gt           0.0408
_refine_ls_restrained_S_all      1.035
_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)+(0.0689P)²+0.9930P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1103
_refine_ls_wR_factor_ref         0.1142
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C7(H7), C8(H8), C9(H9), C11(H11), C12(H12), C13(H13),
 C14(H14), C15(H15), C17(H17), C18(H18), C19(H19), C20(H20), C21(H21), C23(H23),
  C24(H24), C25(H25), C26(H26), C27(H27)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
S1 S 0.34699(5) 0.45925(5) 0.39822(5) 0.01727(15) Uani 1 1 d . . . . .
S2 S 0.62244(5) 0.53373(5) 0.29130(5) 0.01725(15) Uani 1 1 d . . . . .
S3 S 0.45427(6) 0.74377(6) 0.30413(6) 0.02364(16) Uani 1 1 d . . . . .
P1 P 0.37121(5) 0.15366(6) 0.46256(6) 0.01585(15) Uani 1 1 d . . . . .
P2 P 0.68604(5) 0.24433(6) 0.34360(5) 0.01481(15) Uani 1 1 d . . . . .
C1 C 0.4729(2) 0.5877(2) 0.3295(2) 0.0166(4) Uani 1 1 d . . . . .
C2 C 0.4394(2) 0.3287(2) 0.3991(2) 0.0151(4) Uani 1 1 d . . . . .
C3 C 0.5695(2) 0.3650(2) 0.3485(2) 0.0146(4) Uani 1 1 d . . . . .
C4 C 0.2105(2) 0.1466(2) 0.5681(2) 0.0161(4) Uani 1 1 d . . . . .
C5 C 0.1019(2) 0.0785(2) 0.5695(2) 0.0209(5) Uani 1 1 d . . . . .
H5 H 0.1088 0.0480 0.5054 0.025 Uiso 1 1 calc R . . . .
C6 C -0.0153(2) 0.0551(3) 0.6633(2) 0.0253(5) Uani 1 1 d . . . . .
H6 H -0.0880 0.0075 0.6640 0.030 Uiso 1 1 calc R . . . .
C7 C -0.0271(2) 0.1005(3) 0.7559(2) 0.0272(5) Uani 1 1 d . . . . .
H7 H -0.1082 0.0859 0.8190 0.033 Uiso 1 1 calc R . . . .
C8 C 0.0796(3) 0.1674(3) 0.7567(2) 0.0260(5) Uani 1 1 d . . . . .
H8 H 0.0715 0.1989 0.8202 0.031 Uiso 1 1 calc R . . . .
C9 C 0.1982(2) 0.1883(2) 0.6650(2) 0.0214(5) Uani 1 1 d . . . . .
H9 H 0.2717 0.2314 0.6680 0.026 Uiso 1 1 calc R . . . .
C10 C 0.3368(2) 0.1643(2) 0.3138(2) 0.0170(5) Uani 1 1 d . . . . .
C11 C 0.3914(2) 0.0736(2) 0.2697(2) 0.0211(5) Uani 1 1 d . . . . .
H11 H 0.4393 0.0067 0.3195 0.025 Uiso 1 1 calc R . . . .
C12 C 0.3757(2) 0.0811(2) 0.1531(2) 0.0254(5) Uani 1 1 d . . . . .
H12 H 0.4126 0.0190 0.1238 0.031 Uiso 1 1 calc R . . . .
C13 C 0.3068(3) 0.1786(3) 0.0797(2) 0.0271(6) Uani 1 1 d . . . . .
H13 H 0.2979 0.1846 -0.0009 0.033 Uiso 1 1 calc R . . . .
C14 C 0.2503(3) 0.2677(3) 0.1238(3) 0.0276(6) Uani 1 1 d . . . . .
H14 H 0.2014 0.3335 0.0743 0.033 Uiso 1 1 calc R . . . .
C15 C 0.2653(2) 0.2607(2) 0.2400(2) 0.0214(5) Uani 1 1 d . . . . .
H15 H 0.2267 0.3220 0.2697 0.026 Uiso 1 1 calc R . . . .
C16 C 0.6955(2) 0.2565(2) 0.1817(2) 0.0169(5) Uani 1 1 d . . . . .
C17 C 0.7600(3) 0.1591(3) 0.1548(2) 0.0263(5) Uani 1 1 d . . . . .
H17 H 0.8034 0.0978 0.2155 0.032 Uiso 1 1 calc R . . . .
C18 C 0.7618(3) 0.1505(3) 0.0409(3) 0.0321(6) Uani 1 1 d . . . . .
H18 H 0.8061 0.0836 0.0241 0.039 Uiso 1 1 calc R . . . .
C19 C 0.6991(2) 0.2393(3) -0.0485(2) 0.0268(5) Uani 1 1 d . . . . .
H19 H 0.6989 0.2325 -0.1259 0.032 Uiso 1 1 calc R . . . .
C20 C 0.6369(2) 0.3377(3) -0.0243(2) 0.0239(5) Uani 1 1 d . . . . .
H20 H 0.5952 0.3996 -0.0864 0.029 Uiso 1 1 calc R . . . .
C21 C 0.6345(2) 0.3473(2) 0.0891(2) 0.0194(5) Uani 1 1 d . . . . .
H21 H 0.5914 0.4157 0.1042 0.023 Uiso 1 1 calc R . . . .
C22 C 0.8342(2) 0.3470(2) 0.3117(2) 0.0171(5) Uani 1 1 d . . . . .
C23 C 0.8709(2) 0.3263(2) 0.4243(2) 0.0210(5) Uani 1 1 d . . . . .
H23 H 0.8239 0.2573 0.5096 0.025 Uiso 1 1 calc R . . . .
C24 C 0.9758(2) 0.4059(3) 0.4123(3) 0.0253(5) Uani 1 1 d . . . . .
H24 H 1.0000 0.3919 0.4892 0.030 Uiso 1 1 calc R . . . .
C25 C 1.0449(2) 0.5057(3) 0.2881(3) 0.0245(5) Uani 1 1 d . . . . .
H25 H 1.1155 0.5614 0.2801 0.029 Uiso 1 1 calc R . . . .
C26 C 1.0117(2) 0.5250(3) 0.1747(2) 0.0234(5) Uani 1 1 d . . . . .
H26 H 1.0605 0.5925 0.0894 0.028 Uiso 1 1 calc R . . . .
C27 C 0.9071(2) 0.4453(2) 0.1863(2) 0.0211(5) Uani 1 1 d . . . . .
H27 H 0.8850 0.4578 0.1088 0.025 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C1 1.732(2) . ?
S1 C2 1.748(2) . ?
S2 C1 1.730(2) . ?
S2 C3 1.738(2) . ?
S3 C1 1.648(2) . ?
P1 C2 1.834(2) . ?
P1 C4 1.833(2) . ?
P1 C10 1.833(2) . ?
P2 C3 1.834(2) . ?
P2 C16 1.826(2) . ?
P2 C22 1.835(2) . ?
C2 C3 1.359(3) . ?
C4 C5 1.399(3) . ?
C4 C9 1.398(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.384(3) . ?
C6 H6 0.9500 . ?
C6 C7 1.381(4) . ?
C7 H7 0.9500 . ?
C7 C8 1.386(4) . ?
C8 H8 0.9500 . ?
C8 C9 1.387(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.398(3) . ?
C10 C15 1.396(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.391(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.381(4) . ?
C13 H13 0.9500 . ?
C13 C14 1.389(4) . ?
C14 H14 0.9500 . ?
C14 C15 1.386(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.395(3) . ?
C16 C21 1.402(3) . ?
C17 H17 0.9500 . ?
C17 C18 1.386(4) . ?
C18 H18 0.9500 . ?
C18 C19 1.384(4) . ?
C19 H19 0.9500 . ?
C19 C20 1.381(4) . ?
C20 H20 0.9500 . ?
C20 C21 1.383(3) . ?
C21 H21 0.9500 . ?
C22 C23 1.396(3) . ?
C22 C27 1.396(3) . ?
C23 H23 0.9500 . ?
C23 C24 1.388(3) . ?
C24 H24 0.9500 . ?
C24 C25 1.382(4) . ?
C25 H25 0.9500 . ?
C25 C26 1.390(3) . ?
C26 H26 0.9500 . ?
C26 C27 1.387(3) . ?
C27 H27 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
C1 S1 C2 98.09(11) . . ?
C1 S2 C3 97.96(10) . . ?
C4 P1 C2 102.10(10) . . ?
C10 P1 C2 100.73(10) . . ?
C10 P1 C4 103.28(10) . . ?
C3 P2 C22 98.70(10) . . ?
C16 P2 C3 100.92(10) . . ?
C16 P2 C22 103.42(10) . . ?
S2 C1 S1 112.33(12) . . ?
S3 C1 S1 124.39(14) . . ?
S3 C1 S2 123.27(14) . . ?
S1 C2 P1 124.16(13) . . ?
C3 C2 S1 115.23(17) . . ?
C3 C2 P1 120.61(17) . . ?
S2 C3 P2 120.59(12) . . ?
C2 C3 S2 116.36(17) . . ?
C2 C3 P2 123.03(17) . . ?
C5 C4 P1 120.64(17) . . ?
C9 C4 P1 119.97(17) . . ?
C9 C4 C5 118.5(2) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 C4 120.6(2) . . ?
C6 C5 H5 119.7 . . ?
C5 C6 H6 119.8 . . ?
C7 C6 C5 120.3(2) . . ?
C7 C6 H6 119.8 . . ?
C6 C7 H7 120.1 . . ?
C6 C7 C8 119.9(2) . . ?
C8 C7 H7 120.1 . . ?
C7 C8 H8 119.9 . . ?
C7 C8 C9 120.1(2) . . ?
C9 C8 H8 119.9 . . ?
C4 C9 H9 119.7 . . ?
C8 C9 C4 120.5(2) . . ?
C8 C9 H9 119.7 . . ?
C11 C10 P1 117.07(17) . . ?
C15 C10 P1 123.91(17) . . ?
C15 C10 C11 118.9(2) . . ?
C10 C11 H11 119.9 . . ?
C12 C11 C10 120.2(2) . . ?
C12 C11 H11 119.9 . . ?
C11 C12 H12 119.9 . . ?
C13 C12 C11 120.3(2) . . ?
C13 C12 H12 119.9 . . ?
C12 C13 H13 120.0 . . ?
C12 C13 C14 120.0(2) . . ?
C14 C13 H13 120.0 . . ?
C13 C14 H14 120.0 . . ?
C15 C14 C13 120.0(2) . . ?
C15 C14 H14 120.0 . . ?
C10 C15 H15 119.7 . . ?
C14 C15 C10 120.5(2) . . ?
C14 C15 H15 119.7 . . ?
C17 C16 P2 116.18(17) . . ?
C17 C16 C21 118.3(2) . . ?
C21 C16 P2 125.31(17) . . ?
C16 C17 H17 119.5 . . ?
C18 C17 C16 121.0(2) . . ?
C18 C17 H17 119.5 . . ?
C17 C18 H18 119.9 . . ?
C19 C18 C17 120.1(2) . . ?
C19 C18 H18 119.9 . . ?
C18 C19 H19 120.3 . . ?
C20 C19 C18 119.4(2) . . ?
C20 C19 H19 120.3 . . ?
C19 C20 H20 119.5 . . ?
C19 C20 C21 121.0(2) . . ?
C21 C20 H20 119.5 . . ?
C16 C21 H21 119.9 . . ?
C20 C21 C16 120.2(2) . . ?
C20 C21 H21 119.9 . . ?
C23 C22 P2 115.65(17) . . ?
C27 C22 P2 125.06(17) . . ?
C27 C22 C23 119.2(2) . . ?
C22 C23 H23 119.8 . . ?
C24 C23 C22 120.4(2) . . ?
C24 C23 H23 119.8 . . ?
C23 C24 H24 120.1 . . ?
C25 C24 C23 119.9(2) . . ?
C25 C24 H24 120.1 . . ?
C24 C25 H25 119.8 . . ?
C24 C25 C26 120.4(2) . . ?
C26 C25 H25 119.8 . . ?
C25 C26 H26 120.1 . . ?
C27 C26 C25 119.9(2) . . ?
C27 C26 H26 120.1 . . ?
C22 C27 H27 119.9 . . ?
C26 C27 C22 120.2(2) . . ?
C26 C27 H27 119.9 . . ?

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
S1 C2 C3 S2 -0.2(2) . . . . ?
S1 C2 C3 P2 178.14(11) . . . . ?
P1 C2 C3 S2 179.94(11) . . . . ?
P1 C2 C3 P2 -1.7(3) . . . . ?
P1 C4 C5 C6 170.00(19) . . . . ?
P1 C4 C9 C8 -171.63(19) . . . . ?
P1 C10 C11 C12 -176.22(18) . . . . ?
P1 C10 C15 C14 175.89(19) . . . . ?
P2 C16 C17 C18 173.5(2) . . . . ?
P2 C16 C21 C20 -173.00(18) . . . . ?
P2 C22 C23 C24 -175.05(18) . . . . ?
P2 C22 C27 C26 174.65(18) . . . . ?
C1 S1 C2 P1 179.04(14) . . . . ?
C1 S1 C2 C3 -0.84(19) . . . . ?
C1 S2 C3 P2 -177.26(13) . . . . ?
C1 S2 C3 C2 1.09(19) . . . . ?
C2 S1 C1 S2 1.53(14) . . . . ?
C2 S1 C1 S3 -177.90(15) . . . . ?
C2 P1 C4 C5 139.56(19) . . . . ?
C2 P1 C4 C9 -51.7(2) . . . . ?
C2 P1 C10 C11 124.63(18) . . . . ?
C2 P1 C10 C15 -52.2(2) . . . . ?
C3 S2 C1 S1 -1.59(14) . . . . ?
C3 S2 C1 S3 177.84(14) . . . . ?
C3 P2 C16 C17 -169.23(19) . . . . ?
C3 P2 C16 C21 5.1(2) . . . . ?
C3 P2 C22 C23 93.49(18) . . . . ?
C3 P2 C22 C27 -83.7(2) . . . . ?
C4 P1 C2 S1 -19.25(16) . . . . ?
C4 P1 C2 C3 160.63(18) . . . . ?
C4 P1 C10 C11 -130.07(18) . . . . ?
C4 P1 C10 C15 53.1(2) . . . . ?
C4 C5 C6 C7 0.9(4) . . . . ?
C5 C4 C9 C8 -2.6(3) . . . . ?
C5 C6 C7 C8 -1.3(4) . . . . ?
C6 C7 C8 C9 -0.2(4) . . . . ?
C7 C8 C9 C4 2.2(4) . . . . ?
C9 C4 C5 C6 1.1(4) . . . . ?
C10 P1 C2 S1 86.99(15) . . . . ?
C10 P1 C2 C3 -93.1(2) . . . . ?
C10 P1 C4 C5 35.3(2) . . . . ?
C10 P1 C4 C9 -155.94(18) . . . . ?
C10 C11 C12 C13 0.3(4) . . . . ?
C11 C10 C15 C14 -0.9(3) . . . . ?
C11 C12 C13 C14 -1.4(4) . . . . ?
C12 C13 C14 C15 1.3(4) . . . . ?
C13 C14 C15 C10 -0.1(4) . . . . ?
C15 C10 C11 C12 0.8(3) . . . . ?
C16 P2 C3 S2 -91.94(14) . . . . ?
C16 P2 C3 C2 89.8(2) . . . . ?
C16 P2 C22 C23 -163.01(17) . . . . ?
C16 P2 C22 C27 19.8(2) . . . . ?
C16 C17 C18 C19 0.1(4) . . . . ?
C17 C16 C21 C20 1.2(3) . . . . ?
C17 C18 C19 C20 1.1(4) . . . . ?
C18 C19 C20 C21 -1.1(4) . . . . ?
C19 C20 C21 C16 -0.1(4) . . . . ?
C21 C16 C17 C18 -1.2(4) . . . . ?
C22 P2 C3 S2 13.64(15) . . . . ?
C22 P2 C3 C2 -164.60(19) . . . . ?
C22 P2 C16 C17 89.0(2) . . . . ?
C22 P2 C16 C21 -96.7(2) . . . . ?
C22 C23 C24 C25 -0.4(4) . . . . ?
C23 C22 C27 C26 -2.5(3) . . . . ?
C23 C24 C25 C26 -1.3(4) . . . . ?
C24 C25 C26 C27 1.2(4) . . . . ?
C25 C26 C27 C22 0.7(4) . . . . ?
C27 C22 C23 C24 2.3(3) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_5364
_database_code_depnum_ccdc_archive 'CCDC 2001007'
loop_
_audit_author_name
_audit_author_address
'Gregor Schnakenburg'
;University of Bonn
Germany
;
_audit_update_record             
;
2020-05-04 deposited with the CCDC.	2020-09-04 downloaded from the CCDC.
;
_audit_creation_date             2017-09-22
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelxl_version_number           2013-2
_chemical_name_common            ?
_chemical_name_systematic        AG-174-8
_chemical_formula_moiety         'C15 H11 O P S3'
_chemical_formula_sum            'C15 H11 O P S3'
_chemical_formula_weight         334.39
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

_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/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   8.9993(5)
_cell_length_b                   21.0026(9)
_cell_length_c                   9.2456(5)
_cell_angle_alpha                90
_cell_angle_beta                 118.641(4)
_cell_angle_gamma                90
_cell_volume                     1533.67(15)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6367
_cell_measurement_temperature    123
_cell_measurement_theta_max      29.54
_cell_measurement_theta_min      2.69
_shelx_estimated_absorpt_T_max   0.893
_shelx_estimated_absorpt_T_min   0.846
_exptl_absorpt_coefficient_mu    0.578
_exptl_absorpt_correction_T_max  0.9306
_exptl_absorpt_correction_T_min  0.8079
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   ?
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.448
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.2
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0261
_diffrn_reflns_av_unetI/netI     0.0338
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            7351
_diffrn_reflns_point_group_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.999
_diffrn_reflns_theta_min         2.691
_diffrn_ambient_temperature      123
_diffrn_detector                 'image plate (34 cm diameter)'
_diffrn_detector_area_resol_mean 6.67
_diffrn_detector_type            STOE
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device       '2-circle goniometer'
_diffrn_measurement_device_type  'STOE IPDS-2T'
_diffrn_measurement_method       'rotation method'
_diffrn_radiation_collimation    '0.5 mm diameter, monocapillary'
_diffrn_radiation_monochromator  'plane graphite'
_diffrn_radiation_polarisn_norm  0
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   
'sealed X-ray tube, 12 x 0.4 mm long-fine focus'
_diffrn_source_current           40
_diffrn_source_power             2.00
_diffrn_source_voltage           50
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2861
_reflns_number_total             3619
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_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    'XT (Sheldrick, 2015)'
_refine_diff_density_max         0.373
_refine_diff_density_min         -0.389
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.940
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         3619
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0381
_refine_ls_R_factor_gt           0.0267
_refine_ls_restrained_S_all      0.941
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0420P)²]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0656
_refine_ls_wR_factor_ref         0.0677
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Rigid bond restraints
 S3, C3
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
3.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C5(H5), C6(H6), C7(H7), C8(H8), C9(H9), C11(H11), C12(H12), C13(H13),
 C14(H14), C15(H15)
;
_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
S1 S 0.67242(4) 0.55482(2) 0.86592(4) 0.02566(9) Uani 1 1 d . . . . .
S2 S 0.61875(5) 0.60905(2) 1.12313(5) 0.03521(11) Uani 1 1 d . . . . .
S3 S 0.76716(5) 0.47871(2) 1.16887(5) 0.03829(12) Uani 1 1 d . U . . .
P P 0.54727(4) 0.67659(2) 0.65032(4) 0.01899(9) Uani 1 1 d . . . . .
O O 0.48801(13) 0.74146(5) 0.66045(14) 0.0281(2) Uani 1 1 d . . . . .
C1 C 0.58580(16) 0.63082(7) 0.83022(17) 0.0213(3) Uani 1 1 d . . . . .
C2 C 0.56068(19) 0.65522(8) 0.95062(19) 0.0279(3) Uani 1 1 d . . . . .
H2 H 0.5128 0.6963 0.9411 0.033 Uiso 1 1 calc R . . . .
C3 C 0.68964(16) 0.54398(8) 1.05929(18) 0.0276(3) Uani 1 1 d . U . . .
C4 C 0.39820(16) 0.63233(6) 0.47455(17) 0.0194(3) Uani 1 1 d . . . . .
C5 C 0.30368(17) 0.58248(7) 0.48852(19) 0.0256(3) Uani 1 1 d . . . . .
H5 H 0.3265 0.5675 0.5941 0.031 Uiso 1 1 calc R . . . .
C6 C 0.17582(18) 0.55490(8) 0.3467(2) 0.0322(4) Uani 1 1 d . . . . .
H6 H 0.1114 0.5208 0.3555 0.039 Uiso 1 1 calc R . . . .
C7 C 0.14197(18) 0.57683(8) 0.1934(2) 0.0320(4) Uani 1 1 d . . . . .
H7 H 0.0535 0.5579 0.0973 0.038 Uiso 1 1 calc R . . . .
C8 C 0.23578(19) 0.62617(8) 0.17819(19) 0.0302(3) Uani 1 1 d . . . . .
H8 H 0.2125 0.6409 0.0722 0.036 Uiso 1 1 calc R . . . .
C9 C 0.36393(18) 0.65399(7) 0.31890(18) 0.0244(3) Uani 1 1 d . . . . .
H9 H 0.4285 0.6879 0.3092 0.029 Uiso 1 1 calc R . . . .
C10 C 0.74664(17) 0.67740(7) 0.64926(18) 0.0227(3) Uani 1 1 d . . . . .
C11 C 0.79037(18) 0.63332(8) 0.56454(19) 0.0280(3) Uani 1 1 d . . . . .
H11 H 0.7135 0.6003 0.5037 0.034 Uiso 1 1 calc R . . . .
C12 C 0.9463(2) 0.63722(10) 0.5683(2) 0.0389(4) Uani 1 1 d . . . . .
H12 H 0.9758 0.6072 0.5094 0.047 Uiso 1 1 calc R . . . .
C13 C 1.0588(2) 0.68522(10) 0.6585(2) 0.0459(5) Uani 1 1 d . . . . .
H13 H 1.1650 0.6882 0.6604 0.055 Uiso 1 1 calc R . . . .
C14 C 1.0175(2) 0.72839(10) 0.7451(3) 0.0465(5) Uani 1 1 d . . . . .
H14 H 1.0960 0.7607 0.8079 0.056 Uiso 1 1 calc R . . . .
C15 C 0.8613(2) 0.72504(8) 0.7413(2) 0.0351(4) Uani 1 1 d . . . . .
H15 H 0.8329 0.7550 0.8011 0.042 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C1 1.7372(14) . ?
S1 C3 1.7339(16) . ?
S2 C2 1.7200(17) . ?
S2 C3 1.7275(18) . ?
S3 C3 1.6476(16) . ?
P O 1.4823(10) . ?
P C1 1.8050(15) . ?
P C4 1.7930(14) . ?
P C10 1.7990(14) . ?
C1 C2 1.339(2) . ?
C2 H2 0.9500 . ?
C4 C5 1.394(2) . ?
C4 C9 1.396(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.390(2) . ?
C6 H6 0.9500 . ?
C6 C7 1.379(2) . ?
C7 H7 0.9500 . ?
C7 C8 1.386(2) . ?
C8 H8 0.9500 . ?
C8 C9 1.388(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.386(2) . ?
C10 C15 1.396(2) . ?
C11 H11 0.9500 . ?
C11 C12 1.390(2) . ?
C12 H12 0.9500 . ?
C12 C13 1.388(3) . ?
C13 H13 0.9500 . ?
C13 C14 1.373(3) . ?
C14 H14 0.9500 . ?
C14 C15 1.391(2) . ?
C15 H15 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
C3 S1 C1 97.28(8) . . ?
C2 S2 C3 97.30(8) . . ?
O P C1 110.32(7) . . ?
O P C4 113.47(6) . . ?
O P C10 112.43(7) . . ?
C4 P C1 106.79(6) . . ?
C4 P C10 108.35(7) . . ?
C10 P C1 104.98(6) . . ?
S1 C1 P 122.34(8) . . ?
C2 C1 S1 115.64(12) . . ?
C2 C1 P 121.85(12) . . ?
S2 C2 H2 121.4 . . ?
C1 C2 S2 117.24(13) . . ?
C1 C2 H2 121.4 . . ?
S2 C3 S1 112.54(9) . . ?
S3 C3 S1 123.06(10) . . ?
S3 C3 S2 124.40(10) . . ?
C5 C4 P 122.03(11) . . ?
C5 C4 C9 119.84(13) . . ?
C9 C4 P 117.72(11) . . ?
C4 C5 H5 120.3 . . ?
C6 C5 C4 119.46(15) . . ?
C6 C5 H5 120.3 . . ?
C5 C6 H6 119.8 . . ?
C7 C6 C5 120.37(15) . . ?
C7 C6 H6 119.8 . . ?
C6 C7 H7 119.7 . . ?
C6 C7 C8 120.60(14) . . ?
C8 C7 H7 119.7 . . ?
C7 C8 H8 120.2 . . ?
C7 C8 C9 119.53(15) . . ?
C9 C8 H8 120.2 . . ?
C4 C9 H9 119.9 . . ?
C8 C9 C4 120.20(14) . . ?
C8 C9 H9 119.9 . . ?
C11 C10 P 123.42(11) . . ?
C11 C10 C15 119.74(14) . . ?
C15 C10 P 116.83(12) . . ?
C10 C11 H11 119.9 . . ?
C10 C11 C12 120.22(16) . . ?
C12 C11 H11 119.9 . . ?
C11 C12 H12 120.2 . . ?
C13 C12 C11 119.64(18) . . ?
C13 C12 H12 120.2 . . ?
C12 C13 H13 119.8 . . ?
C14 C13 C12 120.45(16) . . ?
C14 C13 H13 119.8 . . ?
C13 C14 H14 119.9 . . ?
C13 C14 C15 120.29(17) . . ?
C15 C14 H14 119.9 . . ?
C10 C15 H15 120.2 . . ?
C14 C15 C10 119.63(17) . . ?
C14 C15 H15 120.2 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
#END------------------------------------------------------------------------
