# Electronic Supplementary Material (ESI) for Physical Chemistry Chemical Physics.
# This journal is © the Owner Societies 2017

####################################################################### 
# 
# 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_I
_database_code_depnum_ccdc_archive 'CCDC 1574617'
_audit_update_record             
;
2017-09-14 deposited with the CCDC.
2017-11-07 downloaded from the CCDC.
;
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C45 H38 S2'
_chemical_formula_sum            'C45 H38 S2'
_chemical_formula_weight         642.87

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'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   22.8514(4)
_cell_length_b                   12.0435(2)
_cell_length_c                   13.7823(3)
_cell_angle_alpha                90
_cell_angle_beta                 115.7690(10)
_cell_angle_gamma                90
_cell_volume                     3415.83(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    193(2)
_cell_measurement_reflns_used    26203
_cell_measurement_theta_min      3.56
_cell_measurement_theta_max      68.11

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.250
_exptl_crystal_F_000             1360
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    1.641
_shelx_estimated_absorpt_T_min   0.597
_shelx_estimated_absorpt_T_max   0.791
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'NUMABS (Rigaku, 1999)'
_exptl_absorpt_correction_T_min  0.621
_exptl_absorpt_correction_T_max  0.782

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      193(2)
_diffrn_radiation_wavelength     1.54187
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Rotating anode'
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.000
_diffrn_reflns_number            29606
_diffrn_reflns_av_unetI/netI     0.0103
_diffrn_reflns_av_R_equivalents  0.0174
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         4.253
_diffrn_reflns_theta_max         68.240
_diffrn_reflns_theta_full        67.687
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             3113
_reflns_number_gt                2836
_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       'RAPID AUTO (Rigaku, 2004)'
_computing_cell_refinement       'RAPID AUTO'
_computing_data_reduction        'RAPID AUTO'
_computing_structure_solution    'Il Milione (Burla, et al., 2007)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_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)+(0.0656P)²+1.9835P] 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     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3113
_refine_ls_number_parameters     216
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0415
_refine_ls_R_factor_gt           0.0388
_refine_ls_wR_factor_ref         0.1098
_refine_ls_wR_factor_gt          0.1075
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_restrained_S_all      1.070
_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
S1 S 0.44657(2) 0.28971(3) 0.40147(3) 0.03746(15) Uani 1 1 d . . . . .
C1 C 0.5000 0.22381(16) 0.2500 0.0308(4) Uani 1 2 d S T P . .
C2 C 0.47883(7) 0.30728(12) 0.31116(12) 0.0300(3) Uani 1 1 d . . . . .
C3 C 0.48242(6) 0.41578(11) 0.28460(11) 0.0268(3) Uani 1 1 d . . . . .
C4 C 0.44965(7) 0.48915(12) 0.32750(11) 0.0290(3) Uani 1 1 d . . . . .
C5 C 0.43057(7) 0.43096(13) 0.39723(12) 0.0344(3) Uani 1 1 d . . . . .
C6 C 0.39999(8) 0.48301(17) 0.45471(13) 0.0448(4) Uani 1 1 d . . . . .
H6 H 0.3886 0.4415 0.5026 0.054 Uiso 1 1 calc R U . . .
C7 C 0.38712(8) 0.59289(17) 0.44053(14) 0.0498(5) Uani 1 1 d . . . . .
H7 H 0.3695 0.6295 0.4830 0.060 Uiso 1 1 calc R U . . .
C8 C 0.39932(8) 0.65504(15) 0.36342(13) 0.0424(4) Uani 1 1 d . . . . .
C9 C 0.38067(10) 0.76754(16) 0.34176(18) 0.0575(5) Uani 1 1 d . . . . .
H9 H 0.3635 0.8047 0.3845 0.069 Uiso 1 1 calc R U . . .
C10 C 0.38679(10) 0.82406(16) 0.26091(19) 0.0617(6) Uani 1 1 d . . . . .
H10 H 0.3748 0.9001 0.2487 0.074 Uiso 1 1 calc R U . . .
C11 C 0.41069(9) 0.76973(14) 0.19607(16) 0.0498(5) Uani 1 1 d . . . . .
H11 H 0.4131 0.8080 0.1376 0.060 Uiso 1 1 calc R U . . .
C12 C 0.43074(7) 0.66123(13) 0.21645(13) 0.0365(4) Uani 1 1 d . . . . .
H12 H 0.4466 0.6252 0.1713 0.044 Uiso 1 1 calc R U . . .
C13 C 0.42838(7) 0.60234(12) 0.30257(12) 0.0330(3) Uani 1 1 d . . . . .
C14 C 0.44309(7) 0.15366(11) 0.17016(12) 0.0324(3) Uani 1 1 d . . . . .
C15 C 0.37885(7) 0.17965(13) 0.14509(14) 0.0391(4) Uani 1 1 d . . . . .
H15 H 0.3695 0.2387 0.1819 0.047 Uiso 1 1 calc R U . . .
C16 C 0.32821(7) 0.12054(13) 0.06715(14) 0.0408(4) Uani 1 1 d . . . . .
H16 H 0.2848 0.1395 0.0526 0.049 Uiso 1 1 calc R U . . .
C17 C 0.33878(7) 0.03434(12) 0.00950(13) 0.0352(3) Uani 1 1 d . . . . .
C18 C 0.40333(7) 0.00905(12) 0.03498(13) 0.0358(3) Uani 1 1 d . . . . .
H18 H 0.4126 -0.0491 -0.0028 0.043 Uiso 1 1 calc R U . . .
C19 C 0.45445(7) 0.06680(12) 0.11427(13) 0.0354(3) Uani 1 1 d . . . . .
H19 H 0.4979 0.0465 0.1305 0.042 Uiso 1 1 calc R U . . .
C20 C 0.28067(8) -0.02774(14) -0.07656(15) 0.0447(4) Uani 1 1 d . . . . .
C21 C 0.23448(11) 0.05482(19) -0.15873(19) 0.0719(7) Uani 1 1 d . . . . .
H21A H 0.1973 0.0147 -0.2128 0.086 Uiso 1 1 calc R U . . .
H21B H 0.2575 0.0938 -0.1943 0.086 Uiso 1 1 calc R U . . .
H21C H 0.2191 0.1088 -0.1218 0.086 Uiso 1 1 calc R U . . .
C22 C 0.30101(11) -0.1152(2) -0.1353(2) 0.0843(9) Uani 1 1 d . . . . .
H22A H 0.3232 -0.0793 -0.1738 0.101 Uiso 1 1 calc R U . . .
H22B H 0.2624 -0.1543 -0.1869 0.101 Uiso 1 1 calc R U . . .
H22C H 0.3305 -0.1683 -0.0830 0.101 Uiso 1 1 calc R U . . .
C23 C 0.24427(11) -0.08634(19) -0.0201(2) 0.0680(6) Uani 1 1 d . . . . .
H23A H 0.2066 -0.1259 -0.0737 0.082 Uiso 1 1 calc R U . . .
H23B H 0.2296 -0.0311 0.0167 0.082 Uiso 1 1 calc R U . . .
H23C H 0.2734 -0.1394 0.0327 0.082 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
S1 C2 1.7132(15) . ?
S1 C5 1.7357(17) . ?
C1 C2 1.5198(19) 2_655 ?
C1 C2 1.5198(19) . ?
C1 C14 1.5401(17) . ?
C1 C14 1.5401(17) 2_655 ?
C2 C3 1.369(2) . ?
C3 C4 1.4410(19) . ?
C3 C3 1.491(3) 2_655 ?
C4 C5 1.403(2) . ?
C4 C13 1.438(2) . ?
C5 C6 1.411(2) . ?
C6 C7 1.351(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.423(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.413(3) . ?
C8 C13 1.425(2) . ?
C9 C10 1.364(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.396(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.373(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.404(2) . ?
C12 H12 0.9500 . ?
C14 C19 1.389(2) . ?
C14 C15 1.390(2) . ?
C15 C16 1.385(2) . ?
C15 H15 0.9500 . ?
C16 C17 1.391(2) . ?
C16 H16 0.9500 . ?
C17 C18 1.393(2) . ?
C17 C20 1.536(2) . ?
C18 C19 1.390(2) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C20 C22 1.519(3) . ?
C20 C21 1.532(3) . ?
C20 C23 1.536(3) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 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
C2 S1 C5 90.31(7) . . ?
C2 C1 C2 97.18(15) 2_655 . ?
C2 C1 C14 109.89(8) 2_655 . ?
C2 C1 C14 112.68(8) . . ?
C2 C1 C14 112.68(8) 2_655 2_655 ?
C2 C1 C14 109.89(8) . 2_655 ?
C14 C1 C14 113.46(16) . 2_655 ?
C3 C2 C1 114.36(13) . . ?
C3 C2 S1 114.01(11) . . ?
C1 C2 S1 131.49(11) . . ?
C2 C3 C4 111.92(12) . . ?
C2 C3 C3 106.43(9) . 2_655 ?
C4 C3 C3 141.58(8) . 2_655 ?
C5 C4 C13 117.64(13) . . ?
C5 C4 C3 110.26(13) . . ?
C13 C4 C3 131.71(13) . . ?
C4 C5 C6 122.68(15) . . ?
C4 C5 S1 112.89(11) . . ?
C6 C5 S1 124.41(13) . . ?
C7 C6 C5 118.93(16) . . ?
C7 C6 H6 120.5 . . ?
C5 C6 H6 120.5 . . ?
C6 C7 C8 121.47(15) . . ?
C6 C7 H7 119.3 . . ?
C8 C7 H7 119.3 . . ?
C9 C8 C7 121.55(17) . . ?
C9 C8 C13 118.53(18) . . ?
C7 C8 C13 119.86(16) . . ?
C10 C9 C8 121.52(18) . . ?
C10 C9 H9 119.2 . . ?
C8 C9 H9 119.2 . . ?
C9 C10 C11 119.78(17) . . ?
C9 C10 H10 120.1 . . ?
C11 C10 H10 120.1 . . ?
C12 C11 C10 120.24(19) . . ?
C12 C11 H11 119.9 . . ?
C10 C11 H11 119.9 . . ?
C11 C12 C13 121.46(16) . . ?
C11 C12 H12 119.3 . . ?
C13 C12 H12 119.3 . . ?
C12 C13 C8 118.13(14) . . ?
C12 C13 C4 123.22(14) . . ?
C8 C13 C4 118.50(15) . . ?
C19 C14 C15 117.63(14) . . ?
C19 C14 C1 120.41(12) . . ?
C15 C14 C1 121.78(13) . . ?
C16 C15 C14 120.86(15) . . ?
C16 C15 H15 119.6 . . ?
C14 C15 H15 119.6 . . ?
C15 C16 C17 122.19(14) . . ?
C15 C16 H16 118.9 . . ?
C17 C16 H16 118.9 . . ?
C16 C17 C18 116.54(14) . . ?
C16 C17 C20 119.86(14) . . ?
C18 C17 C20 123.60(14) . . ?
C19 C18 C17 121.63(14) . . ?
C19 C18 H18 119.2 . . ?
C17 C18 H18 119.2 . . ?
C14 C19 C18 121.14(14) . . ?
C14 C19 H19 119.4 . . ?
C18 C19 H19 119.4 . . ?
C22 C20 C21 109.16(19) . . ?
C22 C20 C23 108.07(19) . . ?
C21 C20 C23 108.80(17) . . ?
C22 C20 C17 112.74(14) . . ?
C21 C20 C17 109.96(14) . . ?
C23 C20 C17 108.01(15) . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C20 C22 H22A 109.5 . . ?
C20 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C20 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C20 C23 H23A 109.5 . . ?
C20 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C20 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 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
C2 C1 C2 C3 3.92(7) 2_655 . . . ?
C14 C1 C2 C3 -111.18(14) . . . . ?
C14 C1 C2 C3 121.24(13) 2_655 . . . ?
C2 C1 C2 S1 179.33(16) 2_655 . . . ?
C14 C1 C2 S1 64.22(15) . . . . ?
C14 C1 C2 S1 -63.36(15) 2_655 . . . ?
C5 S1 C2 C3 4.67(12) . . . . ?
C5 S1 C2 C1 -170.74(12) . . . . ?
C1 C2 C3 C4 168.05(10) . . . . ?
S1 C2 C3 C4 -8.18(16) . . . . ?
C1 C2 C3 C3 -9.55(18) . . . 2_655 ?
S1 C2 C3 C3 174.22(11) . . . 2_655 ?
C2 C3 C4 C5 8.04(17) . . . . ?
C3 C3 C4 C5 -175.7(2) 2_655 . . . ?
C2 C3 C4 C13 -164.41(15) . . . . ?
C3 C3 C4 C13 11.9(3) 2_655 . . . ?
C13 C4 C5 C6 -9.3(2) . . . . ?
C3 C4 C5 C6 177.08(14) . . . . ?
C13 C4 C5 S1 169.04(11) . . . . ?
C3 C4 C5 S1 -4.61(15) . . . . ?
C2 S1 C5 C4 0.17(12) . . . . ?
C2 S1 C5 C6 178.45(14) . . . . ?
C4 C5 C6 C7 1.5(2) . . . . ?
S1 C5 C6 C7 -176.60(13) . . . . ?
C5 C6 C7 C8 4.7(3) . . . . ?
C6 C7 C8 C9 174.36(17) . . . . ?
C6 C7 C8 C13 -2.8(3) . . . . ?
C7 C8 C9 C10 -173.74(18) . . . . ?
C13 C8 C9 C10 3.5(3) . . . . ?
C8 C9 C10 C11 1.4(3) . . . . ?
C9 C10 C11 C12 -2.9(3) . . . . ?
C10 C11 C12 C13 -0.5(3) . . . . ?
C11 C12 C13 C8 5.3(2) . . . . ?
C11 C12 C13 C4 -179.20(15) . . . . ?
C9 C8 C13 C12 -6.7(2) . . . . ?
C7 C8 C13 C12 170.59(14) . . . . ?
C9 C8 C13 C4 177.62(15) . . . . ?
C7 C8 C13 C4 -5.1(2) . . . . ?
C5 C4 C13 C12 -164.71(14) . . . . ?
C3 C4 C13 C12 7.3(2) . . . . ?
C5 C4 C13 C8 10.8(2) . . . . ?
C3 C4 C13 C8 -177.22(14) . . . . ?
C2 C1 C14 C19 78.42(17) 2_655 . . . ?
C2 C1 C14 C19 -174.41(13) . . . . ?
C14 C1 C14 C19 -48.73(11) 2_655 . . . ?
C2 C1 C14 C15 -96.50(15) 2_655 . . . ?
C2 C1 C14 C15 10.67(19) . . . . ?
C14 C1 C14 C15 136.35(16) 2_655 . . . ?
C19 C14 C15 C16 0.1(2) . . . . ?
C1 C14 C15 C16 175.15(14) . . . . ?
C14 C15 C16 C17 -1.0(3) . . . . ?
C15 C16 C17 C18 0.8(2) . . . . ?
C15 C16 C17 C20 -179.58(16) . . . . ?
C16 C17 C18 C19 0.3(2) . . . . ?
C20 C17 C18 C19 -179.36(15) . . . . ?
C15 C14 C19 C18 0.9(2) . . . . ?
C1 C14 C19 C18 -174.19(13) . . . . ?
C17 C18 C19 C14 -1.1(2) . . . . ?
C16 C17 C20 C22 177.11(19) . . . . ?
C18 C17 C20 C22 -3.3(3) . . . . ?
C16 C17 C20 C21 55.0(2) . . . . ?
C18 C17 C20 C21 -125.35(19) . . . . ?
C16 C17 C20 C23 -63.6(2) . . . . ?
C18 C17 C20 C23 116.05(19) . . . . ?

_refine_diff_density_max         0.287
_refine_diff_density_min         -0.179
_refine_diff_density_rms         0.044

_shelxl_version_number           2014-3

####################################################################### 
# 
# 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_I_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1574619'
_audit_update_record             
;
2017-09-14 deposited with the CCDC.
2017-11-07 downloaded from the CCDC.
;
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C30 H17 O P S2'
_chemical_formula_sum            'C30 H17 O P S2'
_chemical_formula_weight         488.52

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'
O O 0.0492 0.0322 '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'

_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                   12.0140(2)
_cell_length_b                   9.11776(17)
_cell_length_c                   21.2612(4)
_cell_angle_alpha                90
_cell_angle_beta                 104.4257(7)
_cell_angle_gamma                90
_cell_volume                     2255.54(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    193(2)
_cell_measurement_reflns_used    37085
_cell_measurement_theta_min      3.80
_cell_measurement_theta_max      68.25

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.439
_exptl_crystal_F_000             1008
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    2.985
_shelx_estimated_absorpt_T_min   0.317
_shelx_estimated_absorpt_T_max   0.663
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'NUMABS (Rigaku, 1999)'
_exptl_absorpt_correction_T_min  0.220
_exptl_absorpt_correction_T_max  0.639

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      193(2)
_diffrn_radiation_wavelength     1.54187
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Rotating anode'
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.000
_diffrn_reflns_number            40480
_diffrn_reflns_av_unetI/netI     0.0152
_diffrn_reflns_av_R_equivalents  0.0337
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         3.870
_diffrn_reflns_theta_max         68.249
_diffrn_reflns_theta_full        67.687
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4121
_reflns_number_gt                3964
_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       'RAPID AUTO (Rigaku, ????)'
_computing_cell_refinement       'RAPID AUTO'
_computing_data_reduction        'RAPID AUTO'
_computing_structure_solution    'Il Milione (Burla, et al., 2007)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_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)+(0.0548P)²+1.1119P] 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         4121
_refine_ls_number_parameters     307
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0352
_refine_ls_R_factor_gt           0.0344
_refine_ls_wR_factor_ref         0.0931
_refine_ls_wR_factor_gt          0.0924
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_restrained_S_all      1.062
_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
S1 S 0.45725(3) -0.05005(5) 0.34625(2) 0.02987(12) Uani 1 1 d . . . . .
S2 S 0.85572(3) 0.25506(4) 0.51475(2) 0.02686(12) Uani 1 1 d . . . . .
P1 P 0.60179(3) 0.12797(5) 0.46814(2) 0.02540(12) Uani 1 1 d . . . . .
O1 O 0.60462(10) 0.06996(14) 0.53338(5) 0.0324(3) Uani 1 1 d . . . . .
C1 C 0.58205(13) 0.01612(18) 0.39604(8) 0.0263(3) Uani 1 1 d . . . . .
C2 C 0.66774(13) 0.04177(17) 0.36420(8) 0.0237(3) Uani 1 1 d . . . . .
C3 C 0.62874(13) 0.01564(17) 0.29531(8) 0.0246(3) Uani 1 1 d . . . . .
C4 C 0.68119(14) 0.04312(17) 0.24221(8) 0.0255(3) Uani 1 1 d . . . . .
C5 C 0.78314(14) 0.12366(18) 0.24858(8) 0.0273(3) Uani 1 1 d . . . . .
H5 H 0.8192 0.1669 0.2892 0.033 Uiso 1 1 calc R U . . .
C6 C 0.83149(16) 0.1407(2) 0.19677(9) 0.0336(4) Uani 1 1 d . . . . .
H6 H 0.9017 0.1928 0.2024 0.040 Uiso 1 1 calc R U . . .
C7 C 0.77835(17) 0.0821(2) 0.13601(9) 0.0385(4) Uani 1 1 d . . . . .
H7 H 0.8135 0.0918 0.1008 0.046 Uiso 1 1 calc R U . . .
C8 C 0.67519(17) 0.0104(2) 0.12740(8) 0.0362(4) Uani 1 1 d . . . . .
H8 H 0.6382 -0.0268 0.0857 0.043 Uiso 1 1 calc R U . . .
C9 C 0.62326(15) -0.00870(19) 0.17921(8) 0.0300(4) Uani 1 1 d . . . . .
C10 C 0.51253(16) -0.0749(2) 0.16855(9) 0.0353(4) Uani 1 1 d . . . . .
H10 H 0.4762 -0.1111 0.1266 0.042 Uiso 1 1 calc R U . . .
C11 C 0.45809(15) -0.0873(2) 0.21693(9) 0.0343(4) Uani 1 1 d . . . . .
H11 H 0.3827 -0.1269 0.2086 0.041 Uiso 1 1 calc R U . . .
C12 C 0.51569(14) -0.04005(18) 0.28008(8) 0.0281(3) Uani 1 1 d . . . . .
C13 C 0.74147(13) 0.18042(18) 0.45916(7) 0.0257(3) Uani 1 1 d . . . . .
C14 C 0.77161(13) 0.10887(17) 0.40877(7) 0.0237(3) Uani 1 1 d . . . . .
C15 C 0.89449(13) 0.10615(17) 0.41691(7) 0.0233(3) Uani 1 1 d . . . . .
C16 C 0.96612(13) 0.02737(17) 0.38294(7) 0.0244(3) Uani 1 1 d . . . . .
C17 C 0.92577(14) -0.08667(19) 0.33811(8) 0.0277(3) Uani 1 1 d . . . . .
H17 H 0.8479 -0.1172 0.3301 0.033 Uiso 1 1 calc R U . . .
C18 C 0.99804(15) -0.1540(2) 0.30598(9) 0.0332(4) Uani 1 1 d . . . . .
H18 H 0.9697 -0.2308 0.2761 0.040 Uiso 1 1 calc R U . . .
C19 C 1.11347(15) -0.1101(2) 0.31694(9) 0.0361(4) Uani 1 1 d . . . . .
H19 H 1.1615 -0.1528 0.2925 0.043 Uiso 1 1 calc R U . . .
C20 C 1.15633(14) -0.0060(2) 0.36277(9) 0.0330(4) Uani 1 1 d . . . . .
H20 H 1.2350 0.0214 0.3710 0.040 Uiso 1 1 calc R U . . .
C21 C 1.08511(13) 0.06161(19) 0.39814(8) 0.0275(3) Uani 1 1 d . . . . .
C22 C 1.13430(14) 0.1552(2) 0.45162(8) 0.0307(4) Uani 1 1 d . . . . .
H22 H 1.2142 0.1765 0.4612 0.037 Uiso 1 1 calc R U . . .
C23 C 1.06963(14) 0.21440(19) 0.48919(8) 0.0294(4) Uani 1 1 d . . . . .
H23 H 1.1041 0.2710 0.5265 0.035 Uiso 1 1 calc R U . . .
C24 C 0.94948(13) 0.18962(18) 0.47136(8) 0.0252(3) Uani 1 1 d . . . . .
C25 C 0.50112(13) 0.27617(19) 0.44231(8) 0.0280(3) Uani 1 1 d . . . . .
C26 C 0.49535(17) 0.3500(2) 0.38415(9) 0.0401(4) Uani 1 1 d . . . . .
H26 H 0.5447 0.3223 0.3576 0.048 Uiso 1 1 calc R U . . .
C27 C 0.41779(19) 0.4637(2) 0.36501(10) 0.0466(5) Uani 1 1 d . . . . .
H27 H 0.4142 0.5141 0.3254 0.056 Uiso 1 1 calc R U . . .
C28 C 0.34543(17) 0.5039(2) 0.40364(10) 0.0433(5) Uani 1 1 d . . . . .
H28 H 0.2921 0.5817 0.3904 0.052 Uiso 1 1 calc R U . . .
C29 C 0.35074(16) 0.4316(2) 0.46101(10) 0.0386(4) Uani 1 1 d . . . . .
H29 H 0.3008 0.4594 0.4873 0.046 Uiso 1 1 calc R U . . .
C30 C 0.42877(14) 0.3177(2) 0.48089(9) 0.0320(4) Uani 1 1 d . . . . .
H30 H 0.4325 0.2685 0.5208 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
S1 C1 1.7152(16) . ?
S1 C12 1.7241(17) . ?
S2 C13 1.7133(16) . ?
S2 C24 1.7302(16) . ?
P1 O1 1.4770(12) . ?
P1 C13 1.8002(16) . ?
P1 C25 1.8053(17) . ?
P1 C1 1.8069(17) . ?
C1 C2 1.386(2) . ?
C2 C3 1.442(2) . ?
C2 C14 1.497(2) . ?
C3 C12 1.410(2) . ?
C3 C4 1.445(2) . ?
C4 C5 1.405(2) . ?
C4 C9 1.427(2) . ?
C5 C6 1.376(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.397(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.372(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.405(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.427(2) . ?
C10 C11 1.354(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.416(2) . ?
C11 H11 0.9500 . ?
C13 C14 1.378(2) . ?
C14 C15 1.443(2) . ?
C15 C24 1.405(2) . ?
C15 C16 1.445(2) . ?
C16 C17 1.412(2) . ?
C16 C21 1.420(2) . ?
C17 C18 1.376(2) . ?
C17 H17 0.9500 . ?
C18 C19 1.406(2) . ?
C18 H18 0.9500 . ?
C19 C20 1.366(3) . ?
C19 H19 0.9500 . ?
C20 C21 1.413(2) . ?
C20 H20 0.9500 . ?
C21 C22 1.426(2) . ?
C22 C23 1.357(3) . ?
C22 H22 0.9500 . ?
C23 C24 1.416(2) . ?
C23 H23 0.9500 . ?
C25 C30 1.388(2) . ?
C25 C26 1.394(3) . ?
C26 C27 1.386(3) . ?
C26 H26 0.9500 . ?
C27 C28 1.386(3) . ?
C27 H27 0.9500 . ?
C28 C29 1.374(3) . ?
C28 H28 0.9500 . ?
C29 C30 1.392(3) . ?
C29 H29 0.9500 . ?
C30 H30 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 C12 90.80(8) . . ?
C13 S2 C24 90.65(8) . . ?
O1 P1 C13 113.00(7) . . ?
O1 P1 C25 114.24(8) . . ?
C13 P1 C25 109.91(8) . . ?
O1 P1 C1 124.20(8) . . ?
C13 P1 C1 89.36(7) . . ?
C25 P1 C1 103.18(8) . . ?
C2 C1 S1 113.55(12) . . ?
C2 C1 P1 111.27(12) . . ?
S1 C1 P1 129.19(9) . . ?
C1 C2 C3 112.05(14) . . ?
C1 C2 C14 111.31(14) . . ?
C3 C2 C14 135.99(14) . . ?
C12 C3 C2 110.08(14) . . ?
C12 C3 C4 117.74(14) . . ?
C2 C3 C4 132.08(14) . . ?
C5 C4 C9 118.22(15) . . ?
C5 C4 C3 123.67(14) . . ?
C9 C4 C3 118.04(15) . . ?
C6 C5 C4 120.88(16) . . ?
C6 C5 H5 119.6 . . ?
C4 C5 H5 119.6 . . ?
C5 C6 C7 120.69(17) . . ?
C5 C6 H6 119.7 . . ?
C7 C6 H6 119.7 . . ?
C8 C7 C6 119.66(16) . . ?
C8 C7 H7 120.2 . . ?
C6 C7 H7 120.2 . . ?
C7 C8 C9 121.14(16) . . ?
C7 C8 H8 119.4 . . ?
C9 C8 H8 119.4 . . ?
C8 C9 C10 120.43(16) . . ?
C8 C9 C4 119.11(16) . . ?
C10 C9 C4 120.44(15) . . ?
C11 C10 C9 121.48(16) . . ?
C11 C10 H10 119.3 . . ?
C9 C10 H10 119.3 . . ?
C10 C11 C12 118.73(16) . . ?
C10 C11 H11 120.6 . . ?
C12 C11 H11 120.6 . . ?
C3 C12 C11 122.87(16) . . ?
C3 C12 S1 113.35(12) . . ?
C11 C12 S1 123.75(13) . . ?
C14 C13 S2 113.83(12) . . ?
C14 C13 P1 112.90(12) . . ?
S2 C13 P1 129.80(9) . . ?
C13 C14 C15 111.97(14) . . ?
C13 C14 C2 110.29(13) . . ?
C15 C14 C2 137.35(14) . . ?
C24 C15 C14 110.27(14) . . ?
C24 C15 C16 117.69(14) . . ?
C14 C15 C16 131.87(14) . . ?
C17 C16 C21 118.19(15) . . ?
C17 C16 C15 123.80(14) . . ?
C21 C16 C15 117.92(15) . . ?
C18 C17 C16 120.69(15) . . ?
C18 C17 H17 119.7 . . ?
C16 C17 H17 119.7 . . ?
C17 C18 C19 120.63(17) . . ?
C17 C18 H18 119.7 . . ?
C19 C18 H18 119.7 . . ?
C20 C19 C18 119.79(16) . . ?
C20 C19 H19 120.1 . . ?
C18 C19 H19 120.1 . . ?
C19 C20 C21 120.79(16) . . ?
C19 C20 H20 119.6 . . ?
C21 C20 H20 119.6 . . ?
C20 C21 C16 119.46(16) . . ?
C20 C21 C22 119.94(15) . . ?
C16 C21 C22 120.44(15) . . ?
C23 C22 C21 121.52(15) . . ?
C23 C22 H22 119.2 . . ?
C21 C22 H22 119.2 . . ?
C22 C23 C24 118.27(15) . . ?
C22 C23 H23 120.9 . . ?
C24 C23 H23 120.9 . . ?
C15 C24 C23 123.06(15) . . ?
C15 C24 S2 113.02(12) . . ?
C23 C24 S2 123.91(13) . . ?
C30 C25 C26 119.49(16) . . ?
C30 C25 P1 119.67(13) . . ?
C26 C25 P1 120.84(13) . . ?
C27 C26 C25 120.19(18) . . ?
C27 C26 H26 119.9 . . ?
C25 C26 H26 119.9 . . ?
C26 C27 C28 119.95(19) . . ?
C26 C27 H27 120.0 . . ?
C28 C27 H27 120.0 . . ?
C29 C28 C27 120.11(18) . . ?
C29 C28 H28 119.9 . . ?
C27 C28 H28 119.9 . . ?
C28 C29 C30 120.44(18) . . ?
C28 C29 H29 119.8 . . ?
C30 C29 H29 119.8 . . ?
C25 C30 C29 119.82(17) . . ?
C25 C30 H30 120.1 . . ?
C29 C30 H30 120.1 . . ?

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
C12 S1 C1 C2 -1.65(14) . . . . ?
C12 S1 C1 P1 148.32(13) . . . . ?
O1 P1 C1 C2 -127.51(12) . . . . ?
C13 P1 C1 C2 -9.81(13) . . . . ?
C25 P1 C1 C2 100.50(13) . . . . ?
O1 P1 C1 S1 81.98(14) . . . . ?
C13 P1 C1 S1 -160.32(13) . . . . ?
C25 P1 C1 S1 -50.01(14) . . . . ?
S1 C1 C2 C3 3.85(19) . . . . ?
P1 C1 C2 C3 -151.56(12) . . . . ?
S1 C1 C2 C14 176.11(11) . . . . ?
P1 C1 C2 C14 20.70(17) . . . . ?
C1 C2 C3 C12 -4.5(2) . . . . ?
C14 C2 C3 C12 -174.09(17) . . . . ?
C1 C2 C3 C4 171.79(16) . . . . ?
C14 C2 C3 C4 2.2(3) . . . . ?
C12 C3 C4 C5 167.35(15) . . . . ?
C2 C3 C4 C5 -8.7(3) . . . . ?
C12 C3 C4 C9 -9.6(2) . . . . ?
C2 C3 C4 C9 174.31(16) . . . . ?
C9 C4 C5 C6 -5.9(2) . . . . ?
C3 C4 C5 C6 177.17(16) . . . . ?
C4 C5 C6 C7 2.0(3) . . . . ?
C5 C6 C7 C8 1.9(3) . . . . ?
C6 C7 C8 C9 -1.8(3) . . . . ?
C7 C8 C9 C10 175.90(18) . . . . ?
C7 C8 C9 C4 -2.2(3) . . . . ?
C5 C4 C9 C8 5.9(2) . . . . ?
C3 C4 C9 C8 -176.98(15) . . . . ?
C5 C4 C9 C10 -172.18(16) . . . . ?
C3 C4 C9 C10 5.0(2) . . . . ?
C8 C9 C10 C11 -176.35(18) . . . . ?
C4 C9 C10 C11 1.7(3) . . . . ?
C9 C10 C11 C12 -3.3(3) . . . . ?
C2 C3 C12 C11 -174.74(16) . . . . ?
C4 C3 C12 C11 8.4(2) . . . . ?
C2 C3 C12 S1 3.30(18) . . . . ?
C4 C3 C12 S1 -173.58(12) . . . . ?
C10 C11 C12 C3 -1.8(3) . . . . ?
C10 C11 C12 S1 -179.67(14) . . . . ?
C1 S1 C12 C3 -1.04(13) . . . . ?
C1 S1 C12 C11 176.99(16) . . . . ?
C24 S2 C13 C14 -0.48(13) . . . . ?
C24 S2 C13 P1 156.70(13) . . . . ?
O1 P1 C13 C14 122.83(12) . . . . ?
C25 P1 C13 C14 -108.26(13) . . . . ?
C1 P1 C13 C14 -4.46(13) . . . . ?
O1 P1 C13 S2 -34.51(15) . . . . ?
C25 P1 C13 S2 94.40(13) . . . . ?
C1 P1 C13 S2 -161.80(13) . . . . ?
S2 C13 C14 C15 3.51(18) . . . . ?
P1 C13 C14 C15 -157.61(11) . . . . ?
S2 C13 C14 C2 177.59(11) . . . . ?
P1 C13 C14 C2 16.47(17) . . . . ?
C1 C2 C14 C13 -24.18(19) . . . . ?
C3 C2 C14 C13 145.48(18) . . . . ?
C1 C2 C14 C15 147.70(19) . . . . ?
C3 C2 C14 C15 -42.6(3) . . . . ?
C13 C14 C15 C24 -5.46(19) . . . . ?
C2 C14 C15 C24 -177.25(17) . . . . ?
C13 C14 C15 C16 169.54(16) . . . . ?
C2 C14 C15 C16 -2.2(3) . . . . ?
C24 C15 C16 C17 164.23(15) . . . . ?
C14 C15 C16 C17 -10.5(3) . . . . ?
C24 C15 C16 C21 -12.3(2) . . . . ?
C14 C15 C16 C21 172.95(16) . . . . ?
C21 C16 C17 C18 -5.5(2) . . . . ?
C15 C16 C17 C18 177.97(16) . . . . ?
C16 C17 C18 C19 -0.3(3) . . . . ?
C17 C18 C19 C20 4.0(3) . . . . ?
C18 C19 C20 C21 -1.9(3) . . . . ?
C19 C20 C21 C16 -4.0(3) . . . . ?
C19 C20 C21 C22 171.58(17) . . . . ?
C17 C16 C21 C20 7.5(2) . . . . ?
C15 C16 C21 C20 -175.71(15) . . . . ?
C17 C16 C21 C22 -168.00(15) . . . . ?
C15 C16 C21 C22 8.8(2) . . . . ?
C20 C21 C22 C23 -175.76(17) . . . . ?
C16 C21 C22 C23 -0.3(3) . . . . ?
C21 C22 C23 C24 -4.4(3) . . . . ?
C14 C15 C24 C23 -176.07(15) . . . . ?
C16 C15 C24 C23 8.1(2) . . . . ?
C14 C15 C24 S2 5.15(17) . . . . ?
C16 C15 C24 S2 -170.65(11) . . . . ?
C22 C23 C24 C15 0.3(3) . . . . ?
C22 C23 C24 S2 178.97(13) . . . . ?
C13 S2 C24 C15 -2.79(13) . . . . ?
C13 S2 C24 C23 178.45(15) . . . . ?
O1 P1 C25 C30 -4.96(17) . . . . ?
C13 P1 C25 C30 -133.19(14) . . . . ?
C1 P1 C25 C30 132.65(14) . . . . ?
O1 P1 C25 C26 174.79(14) . . . . ?
C13 P1 C25 C26 46.56(17) . . . . ?
C1 P1 C25 C26 -47.60(16) . . . . ?
C30 C25 C26 C27 -0.1(3) . . . . ?
P1 C25 C26 C27 -179.89(16) . . . . ?
C25 C26 C27 C28 -0.2(3) . . . . ?
C26 C27 C28 C29 0.2(3) . . . . ?
C27 C28 C29 C30 0.1(3) . . . . ?
C26 C25 C30 C29 0.5(3) . . . . ?
P1 C25 C30 C29 -179.76(14) . . . . ?
C28 C29 C30 C25 -0.5(3) . . . . ?

_refine_diff_density_max         0.361
_refine_diff_density_min         -0.254
_refine_diff_density_rms         0.054

_shelxl_version_number           2014-3

####################################################################### 
# 
# 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_I_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 1574618'
_audit_update_record             
;
2017-09-14 deposited with the CCDC.
2017-11-07 downloaded from the CCDC.
;
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H15 N O S2, 0.5(C H Cl3)'
_chemical_formula_sum            'C26.50 H15.50 Cl1.50 N O S2'
_chemical_formula_weight         481.19

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'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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'
Cl Cl 0.3639 0.7018 '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                   12.1314(2)
_cell_length_b                   12.3033(2)
_cell_length_c                   14.3697(3)
_cell_angle_alpha                83.5273(7)
_cell_angle_beta                 85.5012(7)
_cell_angle_gamma                81.3505(7)
_cell_volume                     2102.72(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    193(2)
_cell_measurement_reflns_used    34275
_cell_measurement_theta_min      3.10
_cell_measurement_theta_max      68.23

_exptl_crystal_description       platelet
_exptl_crystal_colour            brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.520
_exptl_crystal_F_000             988
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    4.217
_shelx_estimated_absorpt_T_min   0.320
_shelx_estimated_absorpt_T_max   0.729
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'NUMABS (Rigaku, 1999)'
_exptl_absorpt_correction_T_min  0.304
_exptl_absorpt_correction_T_max  0.714

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      193(2)
_diffrn_radiation_wavelength     1.54187
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Rotating anode'
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.000
_diffrn_reflns_number            39772
_diffrn_reflns_av_unetI/netI     0.0178
_diffrn_reflns_av_R_equivalents  0.0247
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.101
_diffrn_reflns_theta_max         68.229
_diffrn_reflns_theta_full        67.687
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measured_fraction_theta_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_point_group_measured_fraction_full 0.986
_reflns_number_total             7590
_reflns_number_gt                6354
_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       'RAPID AUTO (Rigaku, 2004)'
_computing_cell_refinement       'RAPID AUTO'
_computing_data_reduction        'RAPID AUTO'
_computing_structure_solution    'SIR2004 (Burla, et al., 2005)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_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)+(0.0896P)²+3.7989P] 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     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7590
_refine_ls_number_parameters     577
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0762
_refine_ls_R_factor_gt           0.0673
_refine_ls_wR_factor_ref         0.1917
_refine_ls_wR_factor_gt          0.1837
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_restrained_S_all      1.088
_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
Cl1 Cl 0.31561(12) 0.12739(12) 0.72213(11) 0.0810(4) Uani 1 1 d . . . . .
Cl2 Cl 0.50659(12) 0.23354(13) 0.74515(9) 0.0776(4) Uani 1 1 d . . . . .
Cl3 Cl 0.41998(12) 0.24792(14) 0.56378(8) 0.0793(4) Uani 1 1 d . . . . .
S1 S 0.18070(10) 0.58172(8) 0.39499(7) 0.0502(3) Uani 1 1 d . . . . .
S2 S -0.13180(8) 0.30482(9) 0.35245(7) 0.0457(3) Uani 1 1 d . . . . .
S3 S 0.10926(9) 0.56189(7) 0.13895(7) 0.0449(3) Uani 1 1 d . . . . .
S4 S -0.21046(7) 0.29146(9) 0.10305(7) 0.0438(2) Uani 1 1 d . . . . .
O1 O -0.1916(3) 0.5411(3) 0.3591(2) 0.0587(8) Uani 1 1 d . . . . .
O2 O -0.1260(3) 0.6402(2) 0.1504(2) 0.0579(8) Uani 1 1 d . . . . .
N1 N -0.0107(3) 0.4778(3) 0.3742(2) 0.0405(7) Uani 1 1 d . . . . .
N2 N -0.0818(3) 0.4622(2) 0.1224(2) 0.0374(7) Uani 1 1 d . . . . .
C1 C 0.1033(3) 0.4784(3) 0.3806(3) 0.0389(8) Uani 1 1 d . . . . .
C2 C 0.1642(3) 0.3750(3) 0.3733(2) 0.0323(7) Uani 1 1 d . . . . .
C3 C 0.2823(3) 0.3821(3) 0.3663(2) 0.0351(7) Uani 1 1 d . . . . .
C4 C 0.3772(3) 0.3074(3) 0.3362(2) 0.0362(8) Uani 1 1 d . . . . .
C5 C 0.3682(3) 0.2106(3) 0.2954(2) 0.0389(8) Uani 1 1 d . . . . .
H5 H 0.2961 0.1925 0.2884 0.047 Uiso 1 1 calc R U . . .
C6 C 0.4603(4) 0.1417(4) 0.2655(3) 0.0533(10) Uani 1 1 d . . . . .
H6 H 0.4518 0.0766 0.2387 0.064 Uiso 1 1 calc R U . . .
C7 C 0.5669(4) 0.1675(4) 0.2745(3) 0.0631(13) Uani 1 1 d . . . . .
H7 H 0.6309 0.1186 0.2555 0.076 Uiso 1 1 calc R U . . .
C8 C 0.5794(3) 0.2612(5) 0.3098(3) 0.0604(13) Uani 1 1 d . . . . .
H8 H 0.6526 0.2777 0.3147 0.073 Uiso 1 1 calc R U . . .
C9 C 0.4859(3) 0.3365(4) 0.3400(3) 0.0483(10) Uani 1 1 d . . . . .
C10 C 0.4993(4) 0.4399(4) 0.3699(3) 0.0594(12) Uani 1 1 d . . . . .
H10 H 0.5722 0.4562 0.3768 0.071 Uiso 1 1 calc R U . . .
C11 C 0.4098(4) 0.5149(4) 0.3885(3) 0.0571(12) Uani 1 1 d . . . . .
H11 H 0.4192 0.5857 0.4043 0.069 Uiso 1 1 calc R U . . .
C12 C 0.3014(4) 0.4871(3) 0.3842(3) 0.0455(9) Uani 1 1 d . . . . .
C13 C -0.0195(3) 0.3688(3) 0.3664(2) 0.0394(8) Uani 1 1 d . . . . .
C14 C 0.0825(3) 0.3003(3) 0.3710(2) 0.0339(7) Uani 1 1 d . . . . .
C15 C 0.0675(3) 0.1850(3) 0.3758(2) 0.0365(8) Uani 1 1 d . . . . .
C16 C 0.1393(3) 0.0858(3) 0.4047(2) 0.0405(9) Uani 1 1 d . . . . .
C17 C 0.2401(3) 0.0841(3) 0.4474(3) 0.0442(9) Uani 1 1 d . . . . .
H17 H 0.2629 0.1521 0.4577 0.053 Uiso 1 1 calc R U . . .
C18 C 0.3067(4) -0.0133(4) 0.4747(3) 0.0578(11) Uani 1 1 d . . . . .
H18 H 0.3748 -0.0130 0.5031 0.069 Uiso 1 1 calc R U . . .
C19 C 0.2707(5) -0.1151(4) 0.4593(4) 0.0676(15) Uani 1 1 d . . . . .
H19 H 0.3169 -0.1833 0.4747 0.081 Uiso 1 1 calc R U . . .
C20 C 0.1714(5) -0.1145(4) 0.4229(3) 0.0647(14) Uani 1 1 d . . . . .
H20 H 0.1484 -0.1831 0.4146 0.078 Uiso 1 1 calc R U . . .
C21 C 0.1009(4) -0.0167(3) 0.3968(3) 0.0503(10) Uani 1 1 d . . . . .
C22 C -0.0097(4) -0.0167(4) 0.3673(3) 0.0538(11) Uani 1 1 d . . . . .
H22 H -0.0326 -0.0852 0.3583 0.065 Uiso 1 1 calc R U . . .
C23 C -0.0818(4) 0.0765(4) 0.3519(3) 0.0521(11) Uani 1 1 d . . . . .
H23 H -0.1561 0.0736 0.3369 0.062 Uiso 1 1 calc R U . . .
C24 C -0.0451(4) 0.1791(4) 0.3584(3) 0.0487(10) Uani 1 1 d . . . . .
C25 C -0.1011(4) 0.5643(4) 0.3709(3) 0.0495(10) Uani 1 1 d . . . . .
C26 C -0.0753(4) 0.6769(4) 0.3797(3) 0.0603(12) Uani 1 1 d . . . . .
H26A H 0.0045 0.6730 0.3888 0.072 Uiso 1 1 calc R U . . .
H26B H -0.0942 0.7252 0.3225 0.072 Uiso 1 1 calc R U . . .
H26C H -0.1193 0.7066 0.4337 0.072 Uiso 1 1 calc R U . . .
C27 C 0.0333(3) 0.4603(3) 0.1224(2) 0.0374(8) Uani 1 1 d . . . . .
C28 C 0.0917(3) 0.3584(3) 0.1083(2) 0.0329(7) Uani 1 1 d . . . . .
C29 C 0.2101(3) 0.3652(3) 0.0986(2) 0.0340(7) Uani 1 1 d . . . . .
C30 C 0.3039(3) 0.2933(3) 0.0611(2) 0.0358(8) Uani 1 1 d . . . . .
C31 C 0.2915(3) 0.2018(3) 0.0143(2) 0.0379(8) Uani 1 1 d . . . . .
H31 H 0.2188 0.1845 0.0084 0.045 Uiso 1 1 calc R U . . .
C32 C 0.3827(3) 0.1371(4) -0.0231(3) 0.0477(9) Uani 1 1 d . . . . .
H32 H 0.3726 0.0755 -0.0542 0.057 Uiso 1 1 calc R U . . .
C33 C 0.4905(3) 0.1613(4) -0.0156(3) 0.0543(11) Uani 1 1 d . . . . .
H33 H 0.5535 0.1142 -0.0389 0.065 Uiso 1 1 calc R U . . .
C34 C 0.5046(3) 0.2521(4) 0.0249(3) 0.0548(11) Uani 1 1 d . . . . .
H34 H 0.5781 0.2690 0.0279 0.066 Uiso 1 1 calc R U . . .
C35 C 0.4135(3) 0.3221(4) 0.0628(3) 0.0454(9) Uani 1 1 d . . . . .
C36 C 0.4277(4) 0.4230(4) 0.0973(3) 0.0537(11) Uani 1 1 d . . . . .
H36 H 0.5010 0.4386 0.1031 0.064 Uiso 1 1 calc R U . . .
C37 C 0.3387(4) 0.4970(4) 0.1221(3) 0.0502(10) Uani 1 1 d . . . . .
H37 H 0.3491 0.5666 0.1401 0.060 Uiso 1 1 calc R U . . .
C38 C 0.2301(3) 0.4689(3) 0.1205(2) 0.0407(8) Uani 1 1 d . . . . .
C39 C -0.0946(3) 0.3531(3) 0.1113(2) 0.0357(7) Uani 1 1 d . . . . .
C40 C 0.0064(3) 0.2849(3) 0.1077(2) 0.0315(7) Uani 1 1 d . . . . .
C41 C -0.0115(3) 0.1705(3) 0.1103(2) 0.0340(7) Uani 1 1 d . . . . .
C42 C 0.0608(3) 0.0688(3) 0.1298(2) 0.0356(8) Uani 1 1 d . . . . .
C43 C 0.1690(3) 0.0618(3) 0.1605(2) 0.0392(8) Uani 1 1 d . . . . .
H43 H 0.1973 0.1279 0.1682 0.047 Uiso 1 1 calc R U . . .
C44 C 0.2347(4) -0.0378(3) 0.1795(3) 0.0491(10) Uani 1 1 d . . . . .
H44 H 0.3077 -0.0401 0.2000 0.059 Uiso 1 1 calc R U . . .
C45 C 0.1939(4) -0.1368(3) 0.1687(3) 0.0576(12) Uani 1 1 d . . . . .
H45 H 0.2405 -0.2058 0.1793 0.069 Uiso 1 1 calc R U . . .
C46 C 0.0874(4) -0.1336(3) 0.1431(3) 0.0535(11) Uani 1 1 d . . . . .
H46 H 0.0603 -0.2008 0.1372 0.064 Uiso 1 1 calc R U . . .
C47 C 0.0169(4) -0.0330(3) 0.1254(3) 0.0448(9) Uani 1 1 d . . . . .
C48 C -0.0971(4) -0.0307(4) 0.1086(3) 0.0501(10) Uani 1 1 d . . . . .
H48 H -0.1241 -0.0981 0.1031 0.060 Uiso 1 1 calc R U . . .
C49 C -0.1678(4) 0.0644(4) 0.1002(3) 0.0475(10) Uani 1 1 d . . . . .
H49 H -0.2449 0.0643 0.0927 0.057 Uiso 1 1 calc R U . . .
C50 C -0.1249(3) 0.1653(3) 0.1027(3) 0.0391(8) Uani 1 1 d . . . . .
C51 C -0.1600(4) 0.5558(3) 0.1382(3) 0.0469(9) Uani 1 1 d . . . . .
C52 C -0.2799(4) 0.5410(4) 0.1407(3) 0.0547(11) Uani 1 1 d . . . . .
H52A H -0.2854 0.4653 0.1287 0.066 Uiso 1 1 calc R U . . .
H52B H -0.3156 0.5549 0.2027 0.066 Uiso 1 1 calc R U . . .
H52C H -0.3174 0.5932 0.0925 0.066 Uiso 1 1 calc R U . . .
C53 C 0.3856(5) 0.2404(5) 0.6842(4) 0.0697(13) Uani 1 1 d . . . . .
H53 H 0.3348 0.3094 0.6978 0.084 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
Cl1 C53 1.750(6) . ?
Cl2 C53 1.754(5) . ?
Cl3 C53 1.743(5) . ?
S1 C1 1.729(4) . ?
S1 C12 1.737(4) . ?
S2 C13 1.708(4) . ?
S2 C24 1.732(5) . ?
S3 C27 1.707(4) . ?
S3 C38 1.741(4) . ?
S4 C39 1.713(4) . ?
S4 C50 1.733(4) . ?
O1 C25 1.205(5) . ?
O2 C51 1.207(5) . ?
N1 C13 1.378(5) . ?
N1 C1 1.395(5) . ?
N1 C25 1.408(5) . ?
N2 C27 1.393(5) . ?
N2 C39 1.402(5) . ?
N2 C51 1.405(5) . ?
C1 C2 1.382(5) . ?
C2 C3 1.443(5) . ?
C2 C14 1.454(5) . ?
C3 C12 1.402(5) . ?
C3 C4 1.432(5) . ?
C4 C5 1.407(5) . ?
C4 C9 1.424(5) . ?
C5 C6 1.368(6) . ?
C5 H5 0.9500 . ?
C6 C7 1.395(7) . ?
C6 H6 0.9500 . ?
C7 C8 1.344(7) . ?
C7 H7 0.9500 . ?
C8 C9 1.425(7) . ?
C8 H8 0.9500 . ?
C9 C10 1.424(6) . ?
C10 C11 1.345(7) . ?
C10 H10 0.9500 . ?
C11 C12 1.415(6) . ?
C11 H11 0.9500 . ?
C13 C14 1.390(5) . ?
C14 C15 1.451(5) . ?
C15 C24 1.421(5) . ?
C15 C16 1.429(6) . ?
C16 C17 1.407(6) . ?
C16 C21 1.427(5) . ?
C17 C18 1.377(6) . ?
C17 H17 0.9500 . ?
C18 C19 1.432(7) . ?
C18 H18 0.9500 . ?
C19 C20 1.349(8) . ?
C19 H19 0.9500 . ?
C20 C21 1.399(7) . ?
C20 H20 0.9500 . ?
C21 C22 1.440(7) . ?
C22 C23 1.341(7) . ?
C22 H22 0.9500 . ?
C23 C24 1.416(5) . ?
C23 H23 0.9500 . ?
C25 C26 1.486(6) . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C27 C28 1.372(5) . ?
C28 C29 1.446(5) . ?
C28 C40 1.474(5) . ?
C29 C38 1.407(5) . ?
C29 C30 1.441(5) . ?
C30 C31 1.408(5) . ?
C30 C35 1.428(5) . ?
C31 C32 1.373(5) . ?
C31 H31 0.9500 . ?
C32 C33 1.398(6) . ?
C32 H32 0.9500 . ?
C33 C34 1.355(7) . ?
C33 H33 0.9500 . ?
C34 C35 1.409(6) . ?
C34 H34 0.9500 . ?
C35 C36 1.426(6) . ?
C36 C37 1.356(7) . ?
C36 H36 0.9500 . ?
C37 C38 1.414(5) . ?
C37 H37 0.9500 . ?
C39 C40 1.378(5) . ?
C40 C41 1.452(5) . ?
C41 C50 1.400(5) . ?
C41 C42 1.430(5) . ?
C42 C43 1.404(5) . ?
C42 C47 1.442(5) . ?
C43 C44 1.370(5) . ?
C43 H43 0.9500 . ?
C44 C45 1.411(6) . ?
C44 H44 0.9500 . ?
C45 C46 1.365(7) . ?
C45 H45 0.9500 . ?
C46 C47 1.404(6) . ?
C46 H46 0.9500 . ?
C47 C48 1.418(6) . ?
C48 C49 1.342(6) . ?
C48 H48 0.9500 . ?
C49 C50 1.421(5) . ?
C49 H49 0.9500 . ?
C51 C52 1.490(6) . ?
C52 H52A 0.9800 . ?
C52 H52B 0.9800 . ?
C52 H52C 0.9800 . ?
C53 H53 1.0000 . ?

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 C12 88.88(18) . . ?
C13 S2 C24 89.26(19) . . ?
C27 S3 C38 88.36(17) . . ?
C39 S4 C50 88.85(17) . . ?
C13 N1 C1 104.3(3) . . ?
C13 N1 C25 124.4(3) . . ?
C1 N1 C25 131.2(3) . . ?
C27 N2 C39 104.3(3) . . ?
C27 N2 C51 123.5(3) . . ?
C39 N2 C51 132.0(3) . . ?
C2 C1 N1 111.9(3) . . ?
C2 C1 S1 115.4(3) . . ?
N1 C1 S1 132.7(3) . . ?
C1 C2 C3 110.2(3) . . ?
C1 C2 C14 105.8(3) . . ?
C3 C2 C14 143.8(3) . . ?
C12 C3 C4 117.1(3) . . ?
C12 C3 C2 110.7(3) . . ?
C4 C3 C2 131.9(3) . . ?
C5 C4 C9 117.9(4) . . ?
C5 C4 C3 123.1(3) . . ?
C9 C4 C3 118.8(3) . . ?
C6 C5 C4 121.9(4) . . ?
C6 C5 H5 119.0 . . ?
C4 C5 H5 119.0 . . ?
C5 C6 C7 119.8(4) . . ?
C5 C6 H6 120.1 . . ?
C7 C6 H6 120.1 . . ?
C8 C7 C6 120.3(4) . . ?
C8 C7 H7 119.8 . . ?
C6 C7 H7 119.8 . . ?
C7 C8 C9 121.8(4) . . ?
C7 C8 H8 119.1 . . ?
C9 C8 H8 119.1 . . ?
C10 C9 C8 121.6(4) . . ?
C10 C9 C4 120.4(4) . . ?
C8 C9 C4 118.0(4) . . ?
C11 C10 C9 120.6(4) . . ?
C11 C10 H10 119.7 . . ?
C9 C10 H10 119.7 . . ?
C10 C11 C12 119.3(4) . . ?
C10 C11 H11 120.4 . . ?
C12 C11 H11 120.4 . . ?
C3 C12 C11 122.9(4) . . ?
C3 C12 S1 114.0(3) . . ?
C11 C12 S1 123.0(3) . . ?
N1 C13 C14 112.8(3) . . ?
N1 C13 S2 131.7(3) . . ?
C14 C13 S2 115.5(3) . . ?
C13 C14 C15 111.0(3) . . ?
C13 C14 C2 104.7(3) . . ?
C15 C14 C2 144.2(3) . . ?
C24 C15 C16 119.3(3) . . ?
C24 C15 C14 108.7(3) . . ?
C16 C15 C14 131.4(3) . . ?
C17 C16 C21 118.7(4) . . ?
C17 C16 C15 123.6(3) . . ?
C21 C16 C15 117.5(4) . . ?
C18 C17 C16 121.9(4) . . ?
C18 C17 H17 119.1 . . ?
C16 C17 H17 119.1 . . ?
C17 C18 C19 118.3(5) . . ?
C17 C18 H18 120.8 . . ?
C19 C18 H18 120.8 . . ?
C20 C19 C18 120.2(4) . . ?
C20 C19 H19 119.9 . . ?
C18 C19 H19 119.9 . . ?
C19 C20 C21 122.6(4) . . ?
C19 C20 H20 118.7 . . ?
C21 C20 H20 118.7 . . ?
C20 C21 C16 118.1(4) . . ?
C20 C21 C22 122.2(4) . . ?
C16 C21 C22 119.6(4) . . ?
C23 C22 C21 122.4(4) . . ?
C23 C22 H22 118.8 . . ?
C21 C22 H22 118.8 . . ?
C22 C23 C24 118.8(4) . . ?
C22 C23 H23 120.6 . . ?
C24 C23 H23 120.6 . . ?
C23 C24 C15 121.2(4) . . ?
C23 C24 S2 124.1(4) . . ?
C15 C24 S2 114.6(3) . . ?
O1 C25 N1 117.3(4) . . ?
O1 C25 C26 125.9(4) . . ?
N1 C25 C26 116.8(4) . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C28 C27 N2 112.5(3) . . ?
C28 C27 S3 117.1(3) . . ?
N2 C27 S3 130.4(3) . . ?
C27 C28 C29 109.6(3) . . ?
C27 C28 C40 105.4(3) . . ?
C29 C28 C40 145.0(3) . . ?
C38 C29 C30 117.2(3) . . ?
C38 C29 C28 110.3(3) . . ?
C30 C29 C28 132.0(3) . . ?
C31 C30 C35 118.2(3) . . ?
C31 C30 C29 122.7(3) . . ?
C35 C30 C29 118.8(3) . . ?
C32 C31 C30 121.1(4) . . ?
C32 C31 H31 119.5 . . ?
C30 C31 H31 119.5 . . ?
C31 C32 C33 120.4(4) . . ?
C31 C32 H32 119.8 . . ?
C33 C32 H32 119.8 . . ?
C34 C33 C32 119.8(4) . . ?
C34 C33 H33 120.1 . . ?
C32 C33 H33 120.1 . . ?
C33 C34 C35 121.9(4) . . ?
C33 C34 H34 119.1 . . ?
C35 C34 H34 119.1 . . ?
C34 C35 C36 121.6(4) . . ?
C34 C35 C30 118.4(4) . . ?
C36 C35 C30 119.9(4) . . ?
C37 C36 C35 121.4(4) . . ?
C37 C36 H36 119.3 . . ?
C35 C36 H36 119.3 . . ?
C36 C37 C38 118.8(4) . . ?
C36 C37 H37 120.6 . . ?
C38 C37 H37 120.6 . . ?
C29 C38 C37 123.0(4) . . ?
C29 C38 S3 114.0(3) . . ?
C37 C38 S3 123.0(3) . . ?
C40 C39 N2 112.0(3) . . ?
C40 C39 S4 116.0(3) . . ?
N2 C39 S4 132.0(3) . . ?
C39 C40 C41 110.2(3) . . ?
C39 C40 C28 105.3(3) . . ?
C41 C40 C28 144.4(3) . . ?
C50 C41 C42 117.7(3) . . ?
C50 C41 C40 110.0(3) . . ?
C42 C41 C40 131.8(3) . . ?
C43 C42 C41 123.8(3) . . ?
C43 C42 C47 117.9(4) . . ?
C41 C42 C47 118.1(3) . . ?
C44 C43 C42 121.7(4) . . ?
C44 C43 H43 119.1 . . ?
C42 C43 H43 119.1 . . ?
C43 C44 C45 119.9(4) . . ?
C43 C44 H44 120.0 . . ?
C45 C44 H44 120.0 . . ?
C46 C45 C44 120.0(4) . . ?
C46 C45 H45 120.0 . . ?
C44 C45 H45 120.0 . . ?
C45 C46 C47 121.5(4) . . ?
C45 C46 H46 119.3 . . ?
C47 C46 H46 119.3 . . ?
C46 C47 C48 121.1(4) . . ?
C46 C47 C42 118.7(4) . . ?
C48 C47 C42 120.1(4) . . ?
C49 C48 C47 121.7(3) . . ?
C49 C48 H48 119.2 . . ?
C47 C48 H48 119.2 . . ?
C48 C49 C50 118.6(4) . . ?
C48 C49 H49 120.7 . . ?
C50 C49 H49 120.7 . . ?
C41 C50 C49 123.1(4) . . ?
C41 C50 S4 114.5(3) . . ?
C49 C50 S4 122.4(3) . . ?
O2 C51 N2 118.6(4) . . ?
O2 C51 C52 125.2(4) . . ?
N2 C51 C52 116.2(4) . . ?
C51 C52 H52A 109.5 . . ?
C51 C52 H52B 109.5 . . ?
H52A C52 H52B 109.5 . . ?
C51 C52 H52C 109.5 . . ?
H52A C52 H52C 109.5 . . ?
H52B C52 H52C 109.5 . . ?
Cl3 C53 Cl1 111.4(3) . . ?
Cl3 C53 Cl2 109.9(3) . . ?
Cl1 C53 Cl2 110.7(3) . . ?
Cl3 C53 H53 108.2 . . ?
Cl1 C53 H53 108.2 . . ?
Cl2 C53 H53 108.2 . . ?

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
C13 N1 C1 C2 2.3(4) . . . . ?
C25 N1 C1 C2 -174.5(4) . . . . ?
C13 N1 C1 S1 -178.1(3) . . . . ?
C25 N1 C1 S1 5.1(6) . . . . ?
C12 S1 C1 C2 3.4(3) . . . . ?
C12 S1 C1 N1 -176.2(4) . . . . ?
N1 C1 C2 C3 171.5(3) . . . . ?
S1 C1 C2 C3 -8.2(4) . . . . ?
N1 C1 C2 C14 -5.7(4) . . . . ?
S1 C1 C2 C14 174.6(2) . . . . ?
C1 C2 C3 C12 9.7(4) . . . . ?
C14 C2 C3 C12 -174.9(4) . . . . ?
C1 C2 C3 C4 -163.2(4) . . . . ?
C14 C2 C3 C4 12.2(8) . . . . ?
C12 C3 C4 C5 -164.9(3) . . . . ?
C2 C3 C4 C5 7.6(6) . . . . ?
C12 C3 C4 C9 9.6(5) . . . . ?
C2 C3 C4 C9 -177.9(4) . . . . ?
C9 C4 C5 C6 4.2(5) . . . . ?
C3 C4 C5 C6 178.7(4) . . . . ?
C4 C5 C6 C7 -0.6(6) . . . . ?
C5 C6 C7 C8 -1.9(7) . . . . ?
C6 C7 C8 C9 0.7(7) . . . . ?
C7 C8 C9 C10 -174.6(4) . . . . ?
C7 C8 C9 C4 3.0(6) . . . . ?
C5 C4 C9 C10 172.4(4) . . . . ?
C3 C4 C9 C10 -2.4(5) . . . . ?
C5 C4 C9 C8 -5.2(5) . . . . ?
C3 C4 C9 C8 180.0(3) . . . . ?
C8 C9 C10 C11 172.7(4) . . . . ?
C4 C9 C10 C11 -4.8(6) . . . . ?
C9 C10 C11 C12 4.3(7) . . . . ?
C4 C3 C12 C11 -10.5(6) . . . . ?
C2 C3 C12 C11 175.5(4) . . . . ?
C4 C3 C12 S1 166.6(3) . . . . ?
C2 C3 C12 S1 -7.4(4) . . . . ?
C10 C11 C12 C3 3.6(7) . . . . ?
C10 C11 C12 S1 -173.3(3) . . . . ?
C1 S1 C12 C3 2.5(3) . . . . ?
C1 S1 C12 C11 179.6(4) . . . . ?
C1 N1 C13 C14 2.2(4) . . . . ?
C25 N1 C13 C14 179.4(3) . . . . ?
C1 N1 C13 S2 -177.9(3) . . . . ?
C25 N1 C13 S2 -0.8(6) . . . . ?
C24 S2 C13 N1 -177.0(4) . . . . ?
C24 S2 C13 C14 2.9(3) . . . . ?
N1 C13 C14 C15 172.0(3) . . . . ?
S2 C13 C14 C15 -7.9(4) . . . . ?
N1 C13 C14 C2 -5.6(4) . . . . ?
S2 C13 C14 C2 174.5(2) . . . . ?
C1 C2 C14 C13 6.6(4) . . . . ?
C3 C2 C14 C13 -168.9(5) . . . . ?
C1 C2 C14 C15 -169.5(4) . . . . ?
C3 C2 C14 C15 15.0(9) . . . . ?
C13 C14 C15 C24 9.6(4) . . . . ?
C2 C14 C15 C24 -174.4(4) . . . . ?
C13 C14 C15 C16 -161.8(3) . . . . ?
C2 C14 C15 C16 14.2(7) . . . . ?
C24 C15 C16 C17 -162.3(3) . . . . ?
C14 C15 C16 C17 8.4(6) . . . . ?
C24 C15 C16 C21 12.1(5) . . . . ?
C14 C15 C16 C21 -177.2(3) . . . . ?
C21 C16 C17 C18 5.3(5) . . . . ?
C15 C16 C17 C18 179.6(3) . . . . ?
C16 C17 C18 C19 -0.4(6) . . . . ?
C17 C18 C19 C20 -3.0(6) . . . . ?
C18 C19 C20 C21 1.4(7) . . . . ?
C19 C20 C21 C16 3.5(6) . . . . ?
C19 C20 C21 C22 -173.4(4) . . . . ?
C17 C16 C21 C20 -6.7(5) . . . . ?
C15 C16 C21 C20 178.6(3) . . . . ?
C17 C16 C21 C22 170.2(3) . . . . ?
C15 C16 C21 C22 -4.5(5) . . . . ?
C20 C21 C22 C23 172.7(4) . . . . ?
C16 C21 C22 C23 -4.1(6) . . . . ?
C21 C22 C23 C24 4.7(6) . . . . ?
C22 C23 C24 C15 3.4(6) . . . . ?
C22 C23 C24 S2 -173.1(3) . . . . ?
C16 C15 C24 C23 -12.0(5) . . . . ?
C14 C15 C24 C23 175.4(3) . . . . ?
C16 C15 C24 S2 164.8(3) . . . . ?
C14 C15 C24 S2 -7.8(4) . . . . ?
C13 S2 C24 C23 179.8(3) . . . . ?
C13 S2 C24 C15 3.1(3) . . . . ?
C13 N1 C25 O1 -1.0(6) . . . . ?
C1 N1 C25 O1 175.3(4) . . . . ?
C13 N1 C25 C26 -179.5(4) . . . . ?
C1 N1 C25 C26 -3.2(6) . . . . ?
C39 N2 C27 C28 2.4(4) . . . . ?
C51 N2 C27 C28 178.0(3) . . . . ?
C39 N2 C27 S3 -176.2(3) . . . . ?
C51 N2 C27 S3 -0.6(5) . . . . ?
C38 S3 C27 C28 3.1(3) . . . . ?
C38 S3 C27 N2 -178.3(4) . . . . ?
N2 C27 C28 C29 173.6(3) . . . . ?
S3 C27 C28 C29 -7.6(4) . . . . ?
N2 C27 C28 C40 -5.5(4) . . . . ?
S3 C27 C28 C40 173.4(2) . . . . ?
C27 C28 C29 C38 8.9(4) . . . . ?
C40 C28 C29 C38 -172.6(4) . . . . ?
C27 C28 C29 C30 -162.5(4) . . . . ?
C40 C28 C29 C30 15.9(8) . . . . ?
C38 C29 C30 C31 -163.2(3) . . . . ?
C28 C29 C30 C31 7.8(6) . . . . ?
C38 C29 C30 C35 10.2(5) . . . . ?
C28 C29 C30 C35 -178.8(3) . . . . ?
C35 C30 C31 C32 4.5(5) . . . . ?
C29 C30 C31 C32 178.0(3) . . . . ?
C30 C31 C32 C33 -0.3(6) . . . . ?
C31 C32 C33 C34 -3.1(6) . . . . ?
C32 C33 C34 C35 1.9(6) . . . . ?
C33 C34 C35 C36 -174.0(4) . . . . ?
C33 C34 C35 C30 2.4(6) . . . . ?
C31 C30 C35 C34 -5.5(5) . . . . ?
C29 C30 C35 C34 -179.2(3) . . . . ?
C31 C30 C35 C36 170.9(3) . . . . ?
C29 C30 C35 C36 -2.8(5) . . . . ?
C34 C35 C36 C37 171.1(4) . . . . ?
C30 C35 C36 C37 -5.2(6) . . . . ?
C35 C36 C37 C38 5.2(6) . . . . ?
C30 C29 C38 C37 -10.7(5) . . . . ?
C28 C29 C38 C37 176.5(3) . . . . ?
C30 C29 C38 S3 165.8(3) . . . . ?
C28 C29 C38 S3 -7.0(4) . . . . ?
C36 C37 C38 C29 3.0(6) . . . . ?
C36 C37 C38 S3 -173.2(3) . . . . ?
C27 S3 C38 C29 2.5(3) . . . . ?
C27 S3 C38 C37 179.0(3) . . . . ?
C27 N2 C39 C40 1.9(4) . . . . ?
C51 N2 C39 C40 -173.1(3) . . . . ?
C27 N2 C39 S4 -178.8(3) . . . . ?
C51 N2 C39 S4 6.1(6) . . . . ?
C50 S4 C39 C40 4.1(3) . . . . ?
C50 S4 C39 N2 -175.1(4) . . . . ?
N2 C39 C40 C41 171.5(3) . . . . ?
S4 C39 C40 C41 -7.8(4) . . . . ?
N2 C39 C40 C28 -5.1(4) . . . . ?
S4 C39 C40 C28 175.5(2) . . . . ?
C27 C28 C40 C39 6.3(4) . . . . ?
C29 C28 C40 C39 -172.2(5) . . . . ?
C27 C28 C40 C41 -168.3(4) . . . . ?
C29 C28 C40 C41 13.2(9) . . . . ?
C39 C40 C41 C50 8.2(4) . . . . ?
C28 C40 C41 C50 -177.4(4) . . . . ?
C39 C40 C41 C42 -163.4(3) . . . . ?
C28 C40 C41 C42 11.1(7) . . . . ?
C50 C41 C42 C43 -164.8(3) . . . . ?
C40 C41 C42 C43 6.2(6) . . . . ?
C50 C41 C42 C47 9.8(5) . . . . ?
C40 C41 C42 C47 -179.2(3) . . . . ?
C41 C42 C43 C44 179.1(3) . . . . ?
C47 C42 C43 C44 4.5(5) . . . . ?
C42 C43 C44 C45 -0.2(6) . . . . ?
C43 C44 C45 C46 -2.8(6) . . . . ?
C44 C45 C46 C47 1.1(6) . . . . ?
C45 C46 C47 C48 -173.3(4) . . . . ?
C45 C46 C47 C42 3.3(6) . . . . ?
C43 C42 C47 C46 -6.0(5) . . . . ?
C41 C42 C47 C46 179.1(3) . . . . ?
C43 C42 C47 C48 170.6(3) . . . . ?
C41 C42 C47 C48 -4.3(5) . . . . ?
C46 C47 C48 C49 173.8(4) . . . . ?
C42 C47 C48 C49 -2.8(6) . . . . ?
C47 C48 C49 C50 3.9(6) . . . . ?
C42 C41 C50 C49 -9.1(5) . . . . ?
C40 C41 C50 C49 178.0(3) . . . . ?
C42 C41 C50 S4 167.4(2) . . . . ?
C40 C41 C50 S4 -5.5(4) . . . . ?
C48 C49 C50 C41 2.2(6) . . . . ?
C48 C49 C50 S4 -174.1(3) . . . . ?
C39 S4 C50 C41 1.1(3) . . . . ?
C39 S4 C50 C49 177.6(3) . . . . ?
C27 N2 C51 O2 1.7(5) . . . . ?
C39 N2 C51 O2 176.0(4) . . . . ?
C27 N2 C51 C52 -176.8(3) . . . . ?
C39 N2 C51 C52 -2.6(6) . . . . ?

_refine_diff_density_max         1.753
_refine_diff_density_min         -0.719
_refine_diff_density_rms         0.081

_shelxl_version_number           2014-3

