# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 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 
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data_cu_5685g
_database_code_depnum_ccdc_archive 'CCDC 1941597'
loop_
_audit_author_name
_audit_author_address
'Gregor Schnakenburg'
;University of Bonn
Germany
;
_audit_update_record             
;
2019-07-18 deposited with the CCDC.	2020-08-28 downloaded from the CCDC.
;
_audit_creation_date             2018-09-12
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.04.18 svn.r3501 for OlexSys, GUI svn.r5488)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        IB-305
_chemical_formula_moiety         'C22 H21 N3 O2 P2 S4'
_chemical_formula_sum            'C22 H21 N3 O2 P2 S4'
_chemical_formula_weight         549.60
_chemical_absolute_configuration ad
_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'
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'
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      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
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'

_cell_length_a                   15.3334(4)
_cell_length_b                   11.3840(3)
_cell_length_c                   27.2807(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4762.0(2)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    8683
_cell_measurement_temperature    150
_cell_measurement_theta_max      72.13
_cell_measurement_theta_min      3.24
_shelx_estimated_absorpt_T_max   0.904
_shelx_estimated_absorpt_T_min   0.492
_exptl_absorpt_coefficient_mu    5.167
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.3233
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.1844 before and 0.1276 after correction. The Ratio of minimum to maximum transmission is 0.4290. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.533
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             2272
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.3257
_diffrn_reflns_av_unetI/netI     0.1444
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            76930
_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         67.721
_diffrn_reflns_theta_min         3.240
_diffrn_ambient_temperature      150.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker D8-Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.952
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.996
_reflns_number_gt                6010
_reflns_number_total             8617
_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 v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_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         0.639
_refine_diff_density_min         -1.147
_refine_diff_density_rms         0.167
_refine_ls_abs_structure_details 
;
 Flack x determined using 1965 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.45(5)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     599
_refine_ls_number_reflns         8617
_refine_ls_number_restraints     121
_refine_ls_R_factor_all          0.1461
_refine_ls_R_factor_gt           0.0954
_refine_ls_restrained_S_all      1.015
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1175P)²+54.3529P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2203
_refine_ls_wR_factor_ref         0.2659
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C15') \\sim Ueq, Uanis(C10) \\sim Ueq, Uanis(C6') \\sim Ueq, Uanis(C5')
\\sim Ueq, Uanis(C12) \\sim Ueq, Uanis(C7') \\sim Ueq, Uanis(C2') \\sim Ueq,
Uanis(C1) \\sim Ueq, Uanis(C17') \\sim Ueq, Uanis(C21') \\sim Ueq, Uanis(C13)
\\sim Ueq, Uanis(C9') \\sim Ueq, Uanis(N2') \\sim Ueq: with sigma of 0.002 and
sigma for terminal atoms of 0.004
Uanis(C10') \\sim Ueq, Uanis(C11) \\sim Ueq: with sigma of 0.002 and sigma for
terminal atoms of 0.004
Uanis(C13') \\sim Ueq, Uanis(C18) \\sim Ueq, Uanis(C21) \\sim Ueq, Uanis(C5)
\\sim Ueq, Uanis(C22') \\sim Ueq: with sigma of 0.002 and sigma for terminal
atoms of 0.004
3.a Ternary CH refined with riding coordinates:
 C13(H13), C14(H14), C13'(H13'), C14'(H14')
3.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C5(H5A,H5B), C10(H10A,H10B), C11(H11A,H11B), C4'(H4'A,H4'B),
 C5'(H5'A,H5'B), C10'(H10C,H10D), C11'(H11C,H11D)
3.c Aromatic/amide H refined with riding coordinates:
 C18(H18), C19(H19), C20(H20), C21(H21), C22(H22), C18'(H18'), C19'(H19'),
 C20'(H20'), C21'(H21'), C22'(H22')
3.d Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C12(H12A,H12B,H12C), C6'(H6'A,H6'B,H6'C), C12'(H12D,H12E,H12F)
;
_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 0.7537(3) 0.0083(4) 0.56500(17) 0.0202(10) Uani 1 1 d . . . . .
S2 S 0.7446(3) -0.1013(5) 0.46543(19) 0.0272(11) Uani 1 1 d . . . . .
S3 S 0.4986(3) 0.4222(4) 0.57491(16) 0.0190(9) Uani 1 1 d . . . . .
S4 S 0.3949(3) 0.4232(5) 0.66851(17) 0.0233(10) Uani 1 1 d . . . . .
P1 P 0.7230(3) 0.2335(4) 0.63055(19) 0.0158(11) Uani 1 1 d . . . . .
P2 P 0.6782(3) 0.3595(4) 0.52375(16) 0.0158(9) Uani 1 1 d . . . . .
O1 O 0.7118(10) 0.6190(13) 0.5536(4) 0.028(3) Uani 1 1 d . . . . .
O2 O 0.8227(9) 0.4430(13) 0.6899(5) 0.027(3) Uani 1 1 d . . . . .
N1 N 0.7160(10) 0.1278(15) 0.4902(6) 0.021(4) Uani 1 1 d . . . . .
N2 N 0.5551(10) 0.3280(14) 0.6528(5) 0.015(3) Uani 1 1 d . . . . .
N3 N 0.7524(9) 0.5476(14) 0.6299(6) 0.019(3) Uani 1 1 d . . . . .
C1 C 0.7293(12) 0.1534(16) 0.5729(7) 0.019(4) Uani 1 1 d . U . . .
C2 C 0.7109(10) 0.2052(17) 0.5290(7) 0.015(4) Uani 1 1 d . . . . .
C3 C 0.7367(11) 0.0144(16) 0.5019(6) 0.015(4) Uani 1 1 d . . . . .
C4 C 0.6974(12) 0.1645(17) 0.4391(6) 0.019(4) Uani 1 1 d . . . . .
H4A H 0.6482 0.2208 0.4391 0.022 Uiso 1 1 calc R . . . .
H4B H 0.6797 0.0950 0.4197 0.022 Uiso 1 1 calc R . . . .
C5 C 0.7763(13) 0.2215(19) 0.4153(7) 0.022(4) Uani 1 1 d . U . . .
H5A H 0.7943 0.2906 0.4349 0.027 Uiso 1 1 calc R . . . .
H5B H 0.8253 0.1649 0.4151 0.027 Uiso 1 1 calc R . . . .
C6 C 0.7572(16) 0.260(2) 0.3638(8) 0.032(6) Uani 1 1 d . . . . .
H6A H 0.7434 0.1906 0.3438 0.048 Uiso 1 1 calc GR . . . .
H6B H 0.8084 0.2995 0.3502 0.048 Uiso 1 1 calc GR . . . .
H6C H 0.7074 0.3135 0.3638 0.048 Uiso 1 1 calc GR . . . .
C7 C 0.6206(11) 0.3117(16) 0.6175(7) 0.016(4) Uani 1 1 d . . . . .
C8 C 0.5997(10) 0.3561(14) 0.5737(6) 0.011(3) Uani 1 1 d . . . . .
C9 C 0.4832(11) 0.3890(16) 0.6366(6) 0.015(4) Uani 1 1 d . . . . .
C10 C 0.5614(13) 0.2898(18) 0.7053(7) 0.022(4) Uani 1 1 d . U . . .
H10A H 0.5382 0.3529 0.7265 0.026 Uiso 1 1 calc R . . . .
H10B H 0.6236 0.2781 0.7138 0.026 Uiso 1 1 calc R . . . .
C11 C 0.5123(14) 0.1782(18) 0.7155(8) 0.025(4) Uani 1 1 d . U . . .
H11A H 0.5171 0.1601 0.7509 0.030 Uiso 1 1 calc R . . . .
H11B H 0.4499 0.1912 0.7080 0.030 Uiso 1 1 calc R . . . .
C12 C 0.5435(17) 0.074(2) 0.6869(10) 0.045(6) Uani 1 1 d . U . . .
H12A H 0.5321 0.0867 0.6520 0.067 Uiso 1 1 calc GR . . . .
H12B H 0.5124 0.0036 0.6979 0.067 Uiso 1 1 calc GR . . . .
H12C H 0.6062 0.0636 0.6921 0.067 Uiso 1 1 calc GR . . . .
C13 C 0.7965(12) 0.3569(16) 0.6093(6) 0.016(4) Uani 1 1 d . U . . .
H13 H 0.8574 0.3268 0.6058 0.020 Uiso 1 1 calc R . . . .
C14 C 0.7696(11) 0.4199(16) 0.5622(6) 0.015(4) Uani 1 1 d . . . . .
H14 H 0.8224 0.4285 0.5410 0.018 Uiso 1 1 calc R . . . .
C15 C 0.7412(11) 0.5417(18) 0.5789(7) 0.020(4) Uani 1 1 d . . . . .
C16 C 0.7943(12) 0.4511(17) 0.6482(6) 0.019(4) Uani 1 1 d . . . . .
C17 C 0.7246(12) 0.6415(17) 0.6611(7) 0.019(4) Uani 1 1 d . . . . .
C18 C 0.7428(14) 0.7584(16) 0.6476(9) 0.019(5) Uani 1 1 d . U . . .
H18 H 0.7729 0.7766 0.6182 0.023 Uiso 1 1 calc R . . . .
C19 C 0.7145(12) 0.8460(19) 0.6795(7) 0.023(4) Uani 1 1 d . . . . .
H19 H 0.7266 0.9256 0.6715 0.027 Uiso 1 1 calc R . . . .
C20 C 0.6695(12) 0.8220(19) 0.7223(8) 0.023(4) Uani 1 1 d . . . . .
H20 H 0.6505 0.8838 0.7432 0.027 Uiso 1 1 calc R . . . .
C21 C 0.6524(14) 0.704(2) 0.7344(8) 0.027(5) Uani 1 1 d . U . . .
H21 H 0.6232 0.6847 0.7641 0.032 Uiso 1 1 calc R . . . .
C22 C 0.6785(12) 0.6164(18) 0.7029(7) 0.022(4) Uani 1 1 d . . . . .
H22 H 0.6643 0.5370 0.7102 0.027 Uiso 1 1 calc R . . . .
S1' S 0.4896(3) 0.9867(4) 0.43485(17) 0.0206(10) Uani 1 1 d . . . . .
S2' S 0.4977(3) 1.0922(5) 0.53554(18) 0.0256(11) Uani 1 1 d . . . . .
S3' S 0.7409(3) 0.5668(4) 0.42549(16) 0.0180(9) Uani 1 1 d . . . . .
S4' S 0.8480(3) 0.5659(4) 0.33311(16) 0.0228(10) Uani 1 1 d . . . . .
P1' P 0.5215(3) 0.7647(5) 0.36748(19) 0.0172(11) Uani 1 1 d . . . . .
P2' P 0.5600(3) 0.6317(4) 0.47468(16) 0.0142(9) Uani 1 1 d . . . . .
O1' O 0.5228(9) 0.3754(13) 0.4426(5) 0.026(3) Uani 1 1 d . . . . .
O2' O 0.4327(9) 0.5619(13) 0.3037(5) 0.028(3) Uani 1 1 d . . . . .
N1' N 0.5262(9) 0.8630(15) 0.5099(5) 0.017(3) Uani 1 1 d . . . . .
N2' N 0.6891(9) 0.6640(13) 0.3462(5) 0.014(3) Uani 1 1 d . U . . .
N3' N 0.4900(9) 0.4482(14) 0.3657(5) 0.017(3) Uani 1 1 d . . . . .
C1' C 0.5133(11) 0.8386(16) 0.4266(7) 0.018(4) Uani 1 1 d . . . . .
C2' C 0.5306(11) 0.7851(16) 0.4702(6) 0.013(3) Uani 1 1 d . U . . .
C3' C 0.5063(12) 0.9774(16) 0.4979(6) 0.017(4) Uani 1 1 d . . . . .
C4' C 0.5423(11) 0.8263(18) 0.5607(6) 0.019(4) Uani 1 1 d . . . . .
H4'A H 0.5601 0.8953 0.5804 0.023 Uiso 1 1 calc R . . . .
H4'B H 0.5905 0.7686 0.5615 0.023 Uiso 1 1 calc R . . . .
C5' C 0.4609(13) 0.7718(18) 0.5830(7) 0.021(4) Uani 1 1 d . U . . .
H5'A H 0.4421 0.7035 0.5631 0.025 Uiso 1 1 calc R . . . .
H5'B H 0.4129 0.8299 0.5834 0.025 Uiso 1 1 calc R . . . .
C6' C 0.4819(18) 0.732(2) 0.6359(10) 0.038(6) Uani 1 1 d . U . . .
H6'A H 0.4889 0.8012 0.6569 0.056 Uiso 1 1 calc GR . . . .
H6'B H 0.5360 0.6862 0.6359 0.056 Uiso 1 1 calc GR . . . .
H6'C H 0.4340 0.6834 0.6483 0.056 Uiso 1 1 calc GR . . . .
C7' C 0.6228(11) 0.6839(16) 0.3818(6) 0.016(4) Uani 1 1 d . U . . .
C8' C 0.6394(11) 0.6339(14) 0.4255(6) 0.012(3) Uani 1 1 d . . . . .
C9' C 0.7588(12) 0.6013(16) 0.3648(7) 0.019(4) Uani 1 1 d . U . . .
C10' C 0.6858(12) 0.7042(16) 0.2952(6) 0.017(4) Uani 1 1 d . U . . .
H10C H 0.6244 0.7203 0.2862 0.021 Uiso 1 1 calc R . . . .
H10D H 0.7076 0.6409 0.2735 0.021 Uiso 1 1 calc R . . . .
C11' C 0.7398(13) 0.814(2) 0.2870(8) 0.030(5) Uani 1 1 d . . . . .
H11C H 0.7382 0.8346 0.2518 0.036 Uiso 1 1 calc R . . . .
H11D H 0.8011 0.7974 0.2959 0.036 Uiso 1 1 calc R . . . .
C12' C 0.7084(15) 0.919(2) 0.3166(9) 0.039(6) Uani 1 1 d . . . . .
H12D H 0.6474 0.9360 0.3083 0.059 Uiso 1 1 calc GR . . . .
H12E H 0.7445 0.9878 0.3089 0.059 Uiso 1 1 calc GR . . . .
H12F H 0.7130 0.9015 0.3517 0.059 Uiso 1 1 calc GR . . . .
C13' C 0.4462(12) 0.6427(17) 0.3862(7) 0.021(4) Uani 1 1 d . U . . .
H13' H 0.3850 0.6728 0.3885 0.025 Uiso 1 1 calc R . . . .
C14' C 0.4698(11) 0.5748(17) 0.4334(6) 0.016(4) Uani 1 1 d . . . . .
H14' H 0.4157 0.5664 0.4536 0.019 Uiso 1 1 calc R . . . .
C15' C 0.4975(11) 0.4532(16) 0.4165(6) 0.013(4) Uani 1 1 d . U . . .
C16' C 0.4524(12) 0.5504(18) 0.3460(7) 0.022(4) Uani 1 1 d . . . . .
C17' C 0.5197(12) 0.3520(17) 0.3360(7) 0.019(4) Uani 1 1 d . U . . .
C18' C 0.4996(14) 0.2351(19) 0.3465(9) 0.026(5) Uani 1 1 d . . . . .
H18' H 0.4660 0.2170 0.3748 0.031 Uiso 1 1 calc R . . . .
C19' C 0.5275(13) 0.1464(19) 0.3168(8) 0.025(5) Uani 1 1 d . . . . .
H19' H 0.5136 0.0674 0.3248 0.031 Uiso 1 1 calc R . . . .
C20' C 0.5761(15) 0.170(2) 0.2749(7) 0.029(5) Uani 1 1 d . . . . .
H20' H 0.5950 0.1085 0.2539 0.034 Uiso 1 1 calc R . . . .
C21' C 0.5963(14) 0.2867(19) 0.2645(7) 0.024(4) Uani 1 1 d . U . . .
H21' H 0.6306 0.3041 0.2365 0.028 Uiso 1 1 calc R . . . .
C22' C 0.5681(13) 0.3767(19) 0.2936(7) 0.024(4) Uani 1 1 d . U . . .
H22' H 0.5813 0.4557 0.2852 0.029 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 1.708(19) . ?
S1 C3 1.743(17) . ?
S2 C3 1.655(18) . ?
S3 C8 1.723(16) . ?
S3 C9 1.741(17) . ?
S4 C9 1.657(16) . ?
P1 C1 1.82(2) . ?
P1 C7 1.839(18) . ?
P1 C13 1.892(18) . ?
P2 C2 1.833(19) . ?
P2 C8 1.819(16) . ?
P2 C14 1.880(18) . ?
O1 C15 1.21(2) . ?
O2 C16 1.22(2) . ?
N1 C2 1.38(2) . ?
N1 C3 1.37(3) . ?
N1 C4 1.48(2) . ?
N2 C7 1.40(2) . ?
N2 C9 1.37(2) . ?
N2 C10 1.50(2) . ?
N3 C15 1.40(2) . ?
N3 C16 1.37(2) . ?
N3 C17 1.43(2) . ?
C1 C2 1.36(3) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.52(3) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C6 1.50(3) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 C8 1.34(2) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.50(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.50(3) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13 1.0000 . ?
C13 C14 1.53(2) . ?
C13 C16 1.51(2) . ?
C14 H14 1.0000 . ?
C14 C15 1.52(3) . ?
C17 C18 1.41(3) . ?
C17 C22 1.37(3) . ?
C18 H18 0.9500 . ?
C18 C19 1.39(3) . ?
C19 H19 0.9500 . ?
C19 C20 1.39(3) . ?
C20 H20 0.9500 . ?
C20 C21 1.41(3) . ?
C21 H21 0.9500 . ?
C21 C22 1.37(3) . ?
C22 H22 0.9500 . ?
S1' C1' 1.739(19) . ?
S1' C3' 1.744(18) . ?
S2' C3' 1.667(18) . ?
S3' C8' 1.734(16) . ?
S3' C9' 1.722(18) . ?
S4' C9' 1.669(18) . ?
P1' C1' 1.824(19) . ?
P1' C7' 1.848(18) . ?
P1' C13' 1.877(19) . ?
P2' C2' 1.807(19) . ?
P2' C8' 1.813(16) . ?
P2' C14' 1.896(18) . ?
O1' C15' 1.20(2) . ?
O2' C16' 1.20(2) . ?
N1' C2' 1.40(2) . ?
N1' C3' 1.38(2) . ?
N1' C4' 1.47(2) . ?
N2' C7' 1.42(2) . ?
N2' C9' 1.38(2) . ?
N2' C10' 1.46(2) . ?
N3' C15' 1.39(2) . ?
N3' C16' 1.41(2) . ?
N3' C17' 1.44(2) . ?
C1' C2' 1.36(3) . ?
C4' H4'A 0.9900 . ?
C4' H4'B 0.9900 . ?
C4' C5' 1.52(3) . ?
C5' H5'A 0.9900 . ?
C5' H5'B 0.9900 . ?
C5' C6' 1.55(3) . ?
C6' H6'A 0.9800 . ?
C6' H6'B 0.9800 . ?
C6' H6'C 0.9800 . ?
C7' C8' 1.35(2) . ?
C10' H10C 0.9900 . ?
C10' H10D 0.9900 . ?
C10' C11' 1.52(3) . ?
C11' H11C 0.9900 . ?
C11' H11D 0.9900 . ?
C11' C12' 1.52(3) . ?
C12' H12D 0.9800 . ?
C12' H12E 0.9800 . ?
C12' H12F 0.9800 . ?
C13' H13' 1.0000 . ?
C13' C14' 1.55(2) . ?
C13' C16' 1.52(3) . ?
C14' H14' 1.0000 . ?
C14' C15' 1.52(2) . ?
C17' C18' 1.40(3) . ?
C17' C22' 1.40(3) . ?
C18' H18' 0.9500 . ?
C18' C19' 1.36(3) . ?
C19' H19' 0.9500 . ?
C19' C20' 1.39(3) . ?
C20' H20' 0.9500 . ?
C20' C21' 1.39(3) . ?
C21' H21' 0.9500 . ?
C21' C22' 1.37(3) . ?
C22' H22' 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 C3 93.0(9) . . ?
C8 S3 C9 92.6(8) . . ?
C1 P1 C7 96.9(9) . . ?
C1 P1 C13 94.3(8) . . ?
C7 P1 C13 95.2(8) . . ?
C2 P2 C14 95.9(8) . . ?
C8 P2 C2 95.8(8) . . ?
C8 P2 C14 94.8(8) . . ?
C2 N1 C4 122.0(16) . . ?
C3 N1 C2 116.0(15) . . ?
C3 N1 C4 121.9(15) . . ?
C7 N2 C10 124.7(15) . . ?
C9 N2 C7 114.9(14) . . ?
C9 N2 C10 120.3(14) . . ?
C15 N3 C17 126.2(16) . . ?
C16 N3 C15 112.4(16) . . ?
C16 N3 C17 121.5(15) . . ?
S1 C1 P1 127.2(11) . . ?
C2 C1 S1 110.6(14) . . ?
C2 C1 P1 122.1(15) . . ?
N1 C2 P2 124.6(13) . . ?
C1 C2 P2 122.7(15) . . ?
C1 C2 N1 112.7(17) . . ?
S2 C3 S1 123.4(11) . . ?
N1 C3 S1 107.6(12) . . ?
N1 C3 S2 129.0(14) . . ?
N1 C4 H4A 109.3 . . ?
N1 C4 H4B 109.3 . . ?
N1 C4 C5 111.7(15) . . ?
H4A C4 H4B 107.9 . . ?
C5 C4 H4A 109.3 . . ?
C5 C4 H4B 109.3 . . ?
C4 C5 H5A 109.3 . . ?
C4 C5 H5B 109.3 . . ?
H5A C5 H5B 107.9 . . ?
C6 C5 C4 111.7(17) . . ?
C6 C5 H5A 109.3 . . ?
C6 C5 H5B 109.3 . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
N2 C7 P1 122.9(13) . . ?
C8 C7 P1 124.1(13) . . ?
C8 C7 N2 113.0(15) . . ?
S3 C8 P2 126.9(9) . . ?
C7 C8 S3 111.3(12) . . ?
C7 C8 P2 121.3(13) . . ?
S4 C9 S3 124.6(11) . . ?
N2 C9 S3 108.1(11) . . ?
N2 C9 S4 127.2(13) . . ?
N2 C10 H10A 109.0 . . ?
N2 C10 H10B 109.0 . . ?
N2 C10 C11 112.9(16) . . ?
H10A C10 H10B 107.8 . . ?
C11 C10 H10A 109.0 . . ?
C11 C10 H10B 109.0 . . ?
C10 C11 H11A 108.7 . . ?
C10 C11 H11B 108.7 . . ?
H11A C11 H11B 107.6 . . ?
C12 C11 C10 114.4(19) . . ?
C12 C11 H11A 108.7 . . ?
C12 C11 H11B 108.7 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
P1 C13 H13 109.4 . . ?
C14 C13 P1 116.4(12) . . ?
C14 C13 H13 109.4 . . ?
C16 C13 P1 107.4(13) . . ?
C16 C13 H13 109.4 . . ?
C16 C13 C14 104.6(14) . . ?
P2 C14 H14 108.4 . . ?
C13 C14 P2 119.9(13) . . ?
C13 C14 H14 108.4 . . ?
C15 C14 P2 106.7(12) . . ?
C15 C14 C13 104.6(14) . . ?
C15 C14 H14 108.4 . . ?
O1 C15 N3 125.4(19) . . ?
O1 C15 C14 126.8(17) . . ?
N3 C15 C14 107.8(16) . . ?
O2 C16 N3 124.6(17) . . ?
O2 C16 C13 126.4(17) . . ?
N3 C16 C13 109.0(15) . . ?
C18 C17 N3 119.4(17) . . ?
C22 C17 N3 119.5(18) . . ?
C22 C17 C18 121.1(19) . . ?
C17 C18 H18 121.6 . . ?
C19 C18 C17 117(2) . . ?
C19 C18 H18 121.6 . . ?
C18 C19 H19 118.6 . . ?
C20 C19 C18 123(2) . . ?
C20 C19 H19 118.6 . . ?
C19 C20 H20 120.7 . . ?
C19 C20 C21 118.5(18) . . ?
C21 C20 H20 120.7 . . ?
C20 C21 H21 120.3 . . ?
C22 C21 C20 119.4(19) . . ?
C22 C21 H21 120.3 . . ?
C17 C22 C21 121(2) . . ?
C17 C22 H22 119.4 . . ?
C21 C22 H22 119.4 . . ?
C1' S1' C3' 92.2(9) . . ?
C9' S3' C8' 92.4(8) . . ?
C1' P1' C7' 95.8(8) . . ?
C1' P1' C13' 93.3(8) . . ?
C7' P1' C13' 95.3(8) . . ?
C2' P2' C8' 96.0(8) . . ?
C2' P2' C14' 96.2(8) . . ?
C8' P2' C14' 93.2(8) . . ?
C2' N1' C4' 122.8(16) . . ?
C3' N1' C2' 115.3(14) . . ?
C3' N1' C4' 122.0(15) . . ?
C7' N2' C10' 124.9(14) . . ?
C9' N2' C7' 112.5(14) . . ?
C9' N2' C10' 122.6(14) . . ?
C15' N3' C16' 112.3(15) . . ?
C15' N3' C17' 124.6(15) . . ?
C16' N3' C17' 123.1(15) . . ?
S1' C1' P1' 125.2(11) . . ?
C2' C1' S1' 111.2(14) . . ?
C2' C1' P1' 123.5(14) . . ?
N1' C2' P2' 124.9(13) . . ?
C1' C2' P2' 122.7(14) . . ?
C1' C2' N1' 112.4(16) . . ?
S2' C3' S1' 123.3(11) . . ?
N1' C3' S1' 108.9(12) . . ?
N1' C3' S2' 127.9(14) . . ?
N1' C4' H4'A 109.5 . . ?
N1' C4' H4'B 109.5 . . ?
N1' C4' C5' 110.8(14) . . ?
H4'A C4' H4'B 108.1 . . ?
C5' C4' H4'A 109.5 . . ?
C5' C4' H4'B 109.5 . . ?
C4' C5' H5'A 109.9 . . ?
C4' C5' H5'B 109.9 . . ?
C4' C5' C6' 108.7(17) . . ?
H5'A C5' H5'B 108.3 . . ?
C6' C5' H5'A 109.9 . . ?
C6' C5' H5'B 109.9 . . ?
C5' C6' H6'A 109.5 . . ?
C5' C6' H6'B 109.5 . . ?
C5' C6' H6'C 109.5 . . ?
H6'A C6' H6'B 109.5 . . ?
H6'A C6' H6'C 109.5 . . ?
H6'B C6' H6'C 109.5 . . ?
N2' C7' P1' 122.4(13) . . ?
C8' C7' P1' 123.8(13) . . ?
C8' C7' N2' 113.7(15) . . ?
S3' C8' P2' 126.6(9) . . ?
C7' C8' S3' 110.9(12) . . ?
C7' C8' P2' 122.4(13) . . ?
S4' C9' S3' 125.0(11) . . ?
N2' C9' S3' 110.4(13) . . ?
N2' C9' S4' 124.6(14) . . ?
N2' C10' H10C 109.2 . . ?
N2' C10' H10D 109.2 . . ?
N2' C10' C11' 112.2(15) . . ?
H10C C10' H10D 107.9 . . ?
C11' C10' H10C 109.2 . . ?
C11' C10' H10D 109.2 . . ?
C10' C11' H11C 108.9 . . ?
C10' C11' H11D 108.9 . . ?
C10' C11' C12' 113.5(17) . . ?
H11C C11' H11D 107.7 . . ?
C12' C11' H11C 108.9 . . ?
C12' C11' H11D 108.9 . . ?
C11' C12' H12D 109.5 . . ?
C11' C12' H12E 109.5 . . ?
C11' C12' H12F 109.5 . . ?
H12D C12' H12E 109.5 . . ?
H12D C12' H12F 109.5 . . ?
H12E C12' H12F 109.5 . . ?
P1' C13' H13' 109.9 . . ?
C14' C13' P1' 116.9(13) . . ?
C14' C13' H13' 109.9 . . ?
C16' C13' P1' 106.0(13) . . ?
C16' C13' H13' 109.9 . . ?
C16' C13' C14' 103.9(15) . . ?
P2' C14' H14' 108.1 . . ?
C13' C14' P2' 119.7(13) . . ?
C13' C14' H14' 108.1 . . ?
C15' C14' P2' 106.8(12) . . ?
C15' C14' C13' 105.5(15) . . ?
C15' C14' H14' 108.1 . . ?
O1' C15' N3' 125.9(17) . . ?
O1' C15' C14' 125.5(16) . . ?
N3' C15' C14' 108.5(15) . . ?
O2' C16' N3' 124.1(18) . . ?
O2' C16' C13' 127.0(18) . . ?
N3' C16' C13' 108.8(15) . . ?
C18' C17' N3' 122.7(18) . . ?
C18' C17' C22' 118.5(19) . . ?
C22' C17' N3' 118.7(18) . . ?
C17' C18' H18' 119.5 . . ?
C19' C18' C17' 121(2) . . ?
C19' C18' H18' 119.5 . . ?
C18' C19' H19' 119.6 . . ?
C18' C19' C20' 121(2) . . ?
C20' C19' H19' 119.6 . . ?
C19' C20' H20' 121.0 . . ?
C19' C20' C21' 118(2) . . ?
C21' C20' H20' 121.0 . . ?
C20' C21' H21' 119.1 . . ?
C22' C21' C20' 122(2) . . ?
C22' C21' H21' 119.1 . . ?
C17' C22' H22' 120.1 . . ?
C21' C22' C17' 120(2) . . ?
C21' C22' H22' 120.1 . . ?

_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_5246f
_database_code_depnum_ccdc_archive 'CCDC 1941598'
loop_
_audit_author_name
_audit_author_address
'Gregor Schnakenburg'
;University of Bonn
Germany
;
_audit_update_record             
;
2019-07-18 deposited with the CCDC.	2020-08-28 downloaded from the CCDC.
;
_audit_creation_date             2017-07-03
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.01.04 svn.r3372 for OlexSys, GUI svn.r5292)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        IB-282
_chemical_formula_moiety         'C18 H20 N2 O4 P2 S4'
_chemical_formula_sum            'C18 H20 N2 O4 P2 S4'
_chemical_formula_weight         518.54
_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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   10.1125(6)
_cell_length_b                   10.1260(6)
_cell_length_c                   11.9070(7)
_cell_angle_alpha                77.826(3)
_cell_angle_beta                 75.301(3)
_cell_angle_gamma                89.011(3)
_cell_volume                     1151.99(12)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    7410
_cell_measurement_temperature    100
_cell_measurement_theta_max      30.11
_cell_measurement_theta_min      2.38
_shelx_estimated_absorpt_T_max   0.955
_shelx_estimated_absorpt_T_min   0.873
_exptl_absorpt_coefficient_mu    0.579
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.6499
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.1266 before and 0.0704 after correction. The Ratio of minimum to maximum transmission is 0.8712. 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    1.495
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0723
_diffrn_reflns_av_unetI/netI     0.0597
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            29215
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.000
_diffrn_reflns_theta_min         2.084
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker X8-KappaApexII'
_diffrn_measurement_method       'fine slicing ω and φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed tube'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4440
_reflns_number_total             5556
_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    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.537
_refine_diff_density_min         -0.440
_refine_diff_density_rms         0.100
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     275
_refine_ls_number_reflns         5556
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0710
_refine_ls_R_factor_gt           0.0515
_refine_ls_restrained_S_all      1.061
_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)+(0.0225P)²+2.7851P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1003
_refine_ls_wR_factor_ref         0.1105
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C5(H5A,H5B), C10(H10A,H10B), C11(H11A,H11B)
2.b Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C12(H12A,H12B,H12C), C16(H16A,H16B,H16C), C18(H18A,H18B,H18C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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 0.77063(7) 0.41497(7) 0.46110(7) 0.01457(16) Uani 1 1 d . . . . .
S2 S 1.04703(8) 0.29394(8) 0.42373(7) 0.01877(17) Uani 1 1 d . . . . .
S3 S 0.82988(7) 1.00763(7) 0.44698(7) 0.01596(16) Uani 1 1 d . . . . .
S4 S 0.63181(9) 1.06619(8) 0.66405(7) 0.02227(19) Uani 1 1 d . . . . .
P1 P 0.90183(7) 0.81954(8) 0.26054(7) 0.01362(16) Uani 1 1 d . . . . .
P2 P 0.59824(7) 0.67539(7) 0.40214(7) 0.01221(16) Uani 1 1 d . . . . .
O1 O 0.8173(2) 0.8000(2) -0.01963(19) 0.0212(5) Uani 1 1 d . . . . .
O2 O 0.8309(2) 1.0041(2) 0.0252(2) 0.0219(5) Uani 1 1 d . . . . .
O3 O 0.5354(2) 0.8388(2) 0.08672(19) 0.0181(5) Uani 1 1 d . . . . .
O4 O 0.4527(2) 0.6416(2) 0.2119(2) 0.0209(5) Uani 1 1 d . . . . .
N1 N 0.9857(2) 0.5507(2) 0.3335(2) 0.0134(5) Uani 1 1 d . . . . .
N2 N 0.6040(2) 0.8743(2) 0.5410(2) 0.0139(5) Uani 1 1 d . . . . .
C1 C 0.8796(3) 0.6382(3) 0.3323(3) 0.0138(6) Uani 1 1 d . . . . .
C2 C 0.9468(3) 0.4233(3) 0.3999(3) 0.0144(6) Uani 1 1 d . . . . .
C3 C 0.7555(3) 0.5823(3) 0.3940(3) 0.0137(6) Uani 1 1 d . . . . .
C4 C 1.1290(3) 0.5853(3) 0.2648(3) 0.0172(6) Uani 1 1 d . . . . .
H4A H 1.1916 0.5365 0.3097 0.021 Uiso 1 1 calc R . . . .
H4B H 1.1477 0.6835 0.2537 0.021 Uiso 1 1 calc R . . . .
C5 C 1.1562(3) 0.5476(3) 0.1434(3) 0.0206(7) Uani 1 1 d . . . . .
H5A H 1.2550 0.5622 0.1038 0.025 Uiso 1 1 calc R . . . .
H5B H 1.1331 0.4501 0.1555 0.025 Uiso 1 1 calc R . . . .
C6 C 1.0755(3) 0.6278(3) 0.0616(3) 0.0235(7) Uani 1 1 d . . . . .
H6A H 1.0998 0.6001 -0.0149 0.035 Uiso 1 1 calc GR . . . .
H6B H 1.0976 0.7245 0.0490 0.035 Uiso 1 1 calc GR . . . .
H6C H 0.9774 0.6102 0.0980 0.035 Uiso 1 1 calc GR . . . .
C7 C 0.7909(3) 0.8780(3) 0.3849(3) 0.0143(6) Uani 1 1 d . . . . .
C8 C 0.6775(3) 0.9784(3) 0.5572(3) 0.0166(6) Uani 1 1 d . . . . .
C9 C 0.6671(3) 0.8193(3) 0.4452(3) 0.0137(6) Uani 1 1 d . . . . .
C10 C 0.4745(3) 0.8181(3) 0.6259(3) 0.0167(6) Uani 1 1 d . . . . .
H10A H 0.4129 0.7891 0.5822 0.020 Uiso 1 1 calc R . . . .
H10B H 0.4290 0.8892 0.6661 0.020 Uiso 1 1 calc R . . . .
C11 C 0.4985(3) 0.6983(3) 0.7185(3) 0.0217(7) Uani 1 1 d . . . . .
H11A H 0.5623 0.7261 0.7607 0.026 Uiso 1 1 calc R . . . .
H11B H 0.5406 0.6255 0.6789 0.026 Uiso 1 1 calc R . . . .
C12 C 0.3633(4) 0.6454(4) 0.8076(3) 0.0297(8) Uani 1 1 d . . . . .
H12A H 0.3023 0.6128 0.7663 0.045 Uiso 1 1 calc GR . . . .
H12B H 0.3203 0.7184 0.8446 0.045 Uiso 1 1 calc GR . . . .
H12C H 0.3806 0.5710 0.8690 0.045 Uiso 1 1 calc GR . . . .
C13 C 0.7647(3) 0.8123(3) 0.1818(3) 0.0132(6) Uani 1 1 d . . . . .
C14 C 0.6416(3) 0.7551(3) 0.2399(3) 0.0130(6) Uani 1 1 d . . . . .
C15 C 0.8056(3) 0.8841(3) 0.0541(3) 0.0155(6) Uani 1 1 d . . . . .
C16 C 0.8614(5) 0.8631(4) -0.1453(3) 0.0355(9) Uani 1 1 d . . . . .
H16A H 0.8677 0.7937 -0.1925 0.053 Uiso 1 1 calc GR . . . .
H16B H 0.9513 0.9085 -0.1623 0.053 Uiso 1 1 calc GR . . . .
H16C H 0.7951 0.9295 -0.1658 0.053 Uiso 1 1 calc GR . . . .
C17 C 0.5323(3) 0.7381(3) 0.1796(3) 0.0148(6) Uani 1 1 d . . . . .
C18 C 0.4407(4) 0.8223(4) 0.0169(3) 0.0278(8) Uani 1 1 d . . . . .
H18A H 0.4596 0.8936 -0.0556 0.042 Uiso 1 1 calc GR . . . .
H18B H 0.3467 0.8285 0.0636 0.042 Uiso 1 1 calc GR . . . .
H18C H 0.4517 0.7337 -0.0045 0.042 Uiso 1 1 calc GR . . . .


_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 1.741(3) . ?
S1 C3 1.737(3) . ?
S2 C2 1.663(3) . ?
S3 C7 1.732(3) . ?
S3 C8 1.735(3) . ?
S4 C8 1.670(3) . ?
P1 C1 1.846(3) . ?
P1 C7 1.818(3) . ?
P1 C13 1.870(3) . ?
P2 C3 1.826(3) . ?
P2 C9 1.845(3) . ?
P2 C14 1.871(3) . ?
O1 C15 1.330(4) . ?
O1 C16 1.454(4) . ?
O2 C15 1.203(4) . ?
O3 C17 1.331(4) . ?
O3 C18 1.451(3) . ?
O4 C17 1.209(3) . ?
N1 C1 1.381(4) . ?
N1 C2 1.369(4) . ?
N1 C4 1.479(4) . ?
N2 C8 1.373(4) . ?
N2 C9 1.381(4) . ?
N2 C10 1.474(4) . ?
C1 C3 1.348(4) . ?
C4 C5 1.529(4) . ?
C5 C6 1.523(4) . ?
C7 C9 1.350(4) . ?
C10 C11 1.520(4) . ?
C11 C12 1.526(4) . ?
C13 C14 1.336(4) . ?
C13 C15 1.495(4) . ?
C14 C17 1.493(4) . ?

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 C2 91.97(14) . . ?
C7 S3 C8 91.83(14) . . ?
C1 P1 C13 93.48(12) . . ?
C7 P1 C1 95.63(13) . . ?
C7 P1 C13 94.77(13) . . ?
C3 P2 C9 93.88(13) . . ?
C3 P2 C14 94.79(13) . . ?
C9 P2 C14 94.61(13) . . ?
C15 O1 C16 115.2(2) . . ?
C17 O3 C18 115.2(2) . . ?
C1 N1 C4 124.4(2) . . ?
C2 N1 C1 114.3(2) . . ?
C2 N1 C4 121.3(2) . . ?
C8 N2 C9 114.5(3) . . ?
C8 N2 C10 122.3(3) . . ?
C9 N2 C10 122.9(2) . . ?
N1 C1 P1 124.3(2) . . ?
C3 C1 P1 121.2(2) . . ?
C3 C1 N1 114.4(3) . . ?
S2 C2 S1 123.47(18) . . ?
N1 C2 S1 109.2(2) . . ?
N1 C2 S2 127.3(2) . . ?
S1 C3 P2 127.01(17) . . ?
C1 C3 S1 110.1(2) . . ?
C1 C3 P2 122.9(2) . . ?
N1 C4 C5 110.9(2) . . ?
C6 C5 C4 114.0(3) . . ?
S3 C7 P1 125.92(17) . . ?
C9 C7 S3 110.8(2) . . ?
C9 C7 P1 123.2(2) . . ?
S4 C8 S3 123.84(18) . . ?
N2 C8 S3 109.2(2) . . ?
N2 C8 S4 126.9(2) . . ?
N2 C9 P2 125.3(2) . . ?
C7 C9 P2 121.1(2) . . ?
C7 C9 N2 113.5(3) . . ?
N2 C10 C11 111.4(2) . . ?
C10 C11 C12 110.2(3) . . ?
C14 C13 P1 121.1(2) . . ?
C14 C13 C15 125.6(3) . . ?
C15 C13 P1 113.1(2) . . ?
C13 C14 P2 122.2(2) . . ?
C13 C14 C17 123.1(3) . . ?
C17 C14 P2 114.5(2) . . ?
O1 C15 C13 112.5(2) . . ?
O2 C15 O1 125.6(3) . . ?
O2 C15 C13 121.8(3) . . ?
O3 C17 C14 112.3(2) . . ?
O4 C17 O3 125.0(3) . . ?
O4 C17 C14 122.7(3) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
