# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_added_by_encifer
_database_code_depnum_ccdc_archive 'CCDC 1424341'
_audit_update_record             
;
2015-09-14 deposited with the CCDC.
2015-11-17 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C28 H48 N8 P4 S4, 4(C F3 O3 S), 3(C2 H3 N)'
_chemical_formula_sum            'C38 H57 F12 N11 O12 P4 S8'
_chemical_formula_weight         1468.31

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'
F F 0.0171 0.0103 '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'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.1184(7)
_cell_length_b                   13.9277(10)
_cell_length_c                   25.5013(18)
_cell_angle_alpha                101.1170(10)
_cell_angle_beta                 91.8260(10)
_cell_angle_gamma                94.6210(10)
_cell_volume                     3163.8(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    153(2)
_cell_measurement_reflns_used    900
_cell_measurement_theta_min      1
_cell_measurement_theta_max      22.5

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.541
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1508
_exptl_absorpt_coefficient_mu    0.480
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8854
_exptl_absorpt_correction_T_max  0.9718
_exptl_absorpt_process_details   
; 
 Corrections were done with the SADABS program, utilizing the none merged
 raw data obtained from the integration process. Integration and final cell
 refinement were done with SAINT.

 SADABS reports ratio of Tmin/Tmax =  0.887127

;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      153(1)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'Omega and Phi scans'
_diffrn_detector_area_resol_mean 80
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            32464
_diffrn_reflns_av_R_equivalents  0.0340
_diffrn_reflns_av_sigmaI/netI    0.0520
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_theta_min         0.81
_diffrn_reflns_theta_max         27.88
_reflns_number_total             15043
_reflns_number_gt                11173
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2(Bruker AXS, 2007)'
_computing_cell_refinement       'APEX2(Bruker AXS, 2007)'
_computing_data_reduction        'SAINT,SADABS (Bruker AXS, 2007 )'
_computing_structure_solution    
;
SHELXS-97 , G. M. Sheldrick, Acta Cryst. (2008) A64, 112-122
;
_computing_structure_refinement  
;
SHELXL-97, G. M. Sheldrick, Acta Cryst. (2008) A64, 112-122
;
_computing_molecular_graphics    
;
ORTEP3,L.J. Farrugia, J. Appl. Cryst. (1997) 30, 565
;
_computing_publication_material  ?


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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0528P)²+1.9067P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    noref
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         15043
_refine_ls_number_parameters     785
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0651
_refine_ls_R_factor_gt           0.0456
_refine_ls_wR_factor_ref         0.1207
_refine_ls_wR_factor_gt          0.1102
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C33 C 0.7465(5) 0.3225(4) 0.65685(16) 0.0737(14) Uani 1 1 d . . .
C34 C 0.6275(4) 0.2480(3) 0.63829(15) 0.0531(9) Uani 1 1 d . . .
H34A H 0.5360 0.2695 0.6539 0.080 Uiso 1 1 calc R . .
H34B H 0.6493 0.1867 0.6492 0.080 Uiso 1 1 calc R . .
H34C H 0.6162 0.2370 0.5992 0.080 Uiso 1 1 calc R . .
C35 C 0.5326(4) 0.1029(3) 0.47352(15) 0.0500(9) Uani 1 1 d . . .
C36 C 0.6128(4) 0.0533(3) 0.43013(14) 0.0543(10) Uani 1 1 d . . .
H36A H 0.5517 0.0422 0.3968 0.081 Uiso 1 1 calc R . .
H36B H 0.6380 -0.0100 0.4376 0.081 Uiso 1 1 calc R . .
H36C H 0.7033 0.0939 0.4264 0.081 Uiso 1 1 calc R . .
C37 C 0.5570(5) 0.2937(3) 0.89296(16) 0.0516(9) Uani 1 1 d . . .
C38 C 0.4310(4) 0.2393(3) 0.86126(13) 0.0451(8) Uani 1 1 d . . .
H38A H 0.3590 0.2171 0.8851 0.068 Uiso 1 1 calc R . .
H38B H 0.4636 0.1822 0.8371 0.068 Uiso 1 1 calc R . .
H38C H 0.3855 0.2818 0.8402 0.068 Uiso 1 1 calc R . .
N9 N 0.8362(6) 0.3832(5) 0.67201(18) 0.155(3) Uani 1 1 d . . .
N10 N 0.4676(4) 0.1429(3) 0.50811(15) 0.0664(10) Uani 1 1 d . . .
N11 N 0.6556(5) 0.3358(3) 0.91812(18) 0.0875(13) Uani 1 1 d . . .
C1 C 0.6718(3) 0.38168(18) 0.34055(10) 0.0199(5) Uani 1 1 d . . .
C2 C 0.4687(3) 0.4341(2) 0.37899(11) 0.0296(6) Uani 1 1 d . . .
C3 C 0.5844(3) 0.4989(2) 0.39988(11) 0.0269(6) Uani 1 1 d . . .
C4 C 0.3090(4) 0.4328(3) 0.38986(16) 0.0543(10) Uani 1 1 d . . .
H4A H 0.2915 0.4923 0.4156 0.081 Uiso 1 1 calc R . .
H4B H 0.2790 0.3747 0.4047 0.081 Uiso 1 1 calc R . .
H4C H 0.2515 0.4306 0.3565 0.081 Uiso 1 1 calc R . .
C5 C 0.5893(4) 0.5915(2) 0.44090(13) 0.0397(8) Uani 1 1 d . . .
H5A H 0.4904 0.6008 0.4539 0.060 Uiso 1 1 calc R . .
H5B H 0.6239 0.6472 0.4249 0.060 Uiso 1 1 calc R . .
H5C H 0.6568 0.5872 0.4709 0.060 Uiso 1 1 calc R . .
C6 C 0.4348(3) 0.2794(2) 0.30916(13) 0.0400(8) Uani 1 1 d . . .
H6A H 0.4974 0.2400 0.2846 0.060 Uiso 1 1 calc R . .
H6B H 0.3590 0.3043 0.2886 0.060 Uiso 1 1 calc R . .
H6C H 0.3877 0.2385 0.3322 0.060 Uiso 1 1 calc R . .
C7 C 0.8581(3) 0.5159(2) 0.38619(11) 0.0277(6) Uani 1 1 d . . .
H7A H 0.9308 0.4673 0.3800 0.042 Uiso 1 1 calc R . .
H7B H 0.8695 0.5517 0.4234 0.042 Uiso 1 1 calc R . .
H7C H 0.8736 0.5623 0.3620 0.042 Uiso 1 1 calc R . .
C8 C 0.9780(3) 0.03707(18) 0.33866(10) 0.0200(5) Uani 1 1 d . . .
C9 C 0.9417(3) -0.08770(19) 0.38146(11) 0.0268(6) Uani 1 1 d . . .
C10 C 1.0636(3) -0.0307(2) 0.40455(11) 0.0270(6) Uani 1 1 d . . .
C11 C 0.8679(4) -0.1791(2) 0.39412(14) 0.0432(8) Uani 1 1 d . . .
H11A H 0.9220 -0.1971 0.4241 0.065 Uiso 1 1 calc R . .
H11B H 0.8664 -0.2323 0.3627 0.065 Uiso 1 1 calc R . .
H11C H 0.7667 -0.1680 0.4039 0.065 Uiso 1 1 calc R . .
C12 C 1.1628(4) -0.0400(2) 0.45074(12) 0.0410(8) Uani 1 1 d . . .
H12A H 1.1291 -0.0988 0.4643 0.061 Uiso 1 1 calc R . .
H12B H 1.1609 0.0182 0.4792 0.061 Uiso 1 1 calc R . .
H12C H 1.2636 -0.0455 0.4390 0.061 Uiso 1 1 calc R . .
C13 C 0.7636(3) -0.0868(2) 0.30394(11) 0.0287(6) Uani 1 1 d . . .
H13A H 0.7387 -0.0394 0.2819 0.043 Uiso 1 1 calc R . .
H13B H 0.6790 -0.1016 0.3247 0.043 Uiso 1 1 calc R . .
H13C H 0.7888 -0.1473 0.2808 0.043 Uiso 1 1 calc R . .
C14 C 1.2071(3) 0.1229(2) 0.39067(11) 0.0292(6) Uani 1 1 d . . .
H14A H 1.2990 0.0972 0.3776 0.044 Uiso 1 1 calc R . .
H14B H 1.2174 0.1454 0.4296 0.044 Uiso 1 1 calc R . .
H14C H 1.1859 0.1780 0.3737 0.044 Uiso 1 1 calc R . .
C15 C 1.1724(3) 0.05865(17) 0.13742(9) 0.0174(5) Uani 1 1 d . . .
C16 C 1.2270(3) -0.06041(19) 0.07130(10) 0.0239(6) Uani 1 1 d . . .
C17 C 1.3559(3) -0.00826(19) 0.09197(10) 0.0247(6) Uani 1 1 d . . .
C18 C 1.2000(4) -0.1463(2) 0.02579(12) 0.0381(7) Uani 1 1 d . . .
H18A H 1.2931 -0.1608 0.0091 0.057 Uiso 1 1 calc R . .
H18B H 1.1303 -0.1307 -0.0007 0.057 Uiso 1 1 calc R . .
H18C H 1.1588 -0.2036 0.0392 0.057 Uiso 1 1 calc R . .
C19 C 1.5109(3) -0.0187(2) 0.07675(12) 0.0356(7) Uani 1 1 d . . .
H19A H 1.5140 -0.0759 0.0477 0.053 Uiso 1 1 calc R . .
H19B H 1.5707 -0.0277 0.1078 0.053 Uiso 1 1 calc R . .
H19C H 1.5502 0.0406 0.0647 0.053 Uiso 1 1 calc R . .
C20 C 0.9587(3) -0.0515(2) 0.08942(12) 0.0322(7) Uani 1 1 d . . .
H20A H 0.9386 -0.1147 0.1005 0.048 Uiso 1 1 calc R . .
H20B H 0.9336 -0.0592 0.0511 0.048 Uiso 1 1 calc R . .
H20C H 0.8992 -0.0030 0.1096 0.048 Uiso 1 1 calc R . .
C21 C 1.4276(3) 0.1404(2) 0.16294(11) 0.0245(6) Uani 1 1 d . . .
H21A H 1.3780 0.1840 0.1903 0.037 Uiso 1 1 calc R . .
H21B H 1.4743 0.1788 0.1386 0.037 Uiso 1 1 calc R . .
H21C H 1.5029 0.1090 0.1802 0.037 Uiso 1 1 calc R . .
C22 C 0.8924(3) 0.41855(17) 0.14995(9) 0.0179(5) Uani 1 1 d . . .
C23 C 0.8014(3) 0.50010(19) 0.09084(10) 0.0239(5) Uani 1 1 d . . .
C24 C 0.9131(3) 0.55917(19) 0.12037(11) 0.0233(5) Uani 1 1 d . . .
C25 C 0.7003(4) 0.5180(2) 0.04737(12) 0.0361(7) Uani 1 1 d . . .
H25A H 0.7253 0.5840 0.0404 0.054 Uiso 1 1 calc R . .
H25B H 0.5984 0.5126 0.0583 0.054 Uiso 1 1 calc R . .
H25C H 0.7106 0.4691 0.0148 0.054 Uiso 1 1 calc R . .
C26 C 0.9712(4) 0.6616(2) 0.11846(14) 0.0378(7) Uani 1 1 d . . .
H26A H 0.9169 0.6847 0.0902 0.057 Uiso 1 1 calc R . .
H26B H 1.0760 0.6629 0.1110 0.057 Uiso 1 1 calc R . .
H26C H 0.9588 0.7046 0.1530 0.057 Uiso 1 1 calc R . .
C27 C 0.6784(3) 0.33231(19) 0.09020(11) 0.0257(6) Uani 1 1 d . . .
H27A H 0.7097 0.2718 0.0996 0.039 Uiso 1 1 calc R . .
H27B H 0.6648 0.3234 0.0512 0.039 Uiso 1 1 calc R . .
H27C H 0.5853 0.3474 0.1067 0.039 Uiso 1 1 calc R . .
C28 C 1.0894(3) 0.5467(2) 0.19596(12) 0.0340(7) Uani 1 1 d . . .
H28A H 1.1123 0.4964 0.2163 0.051 Uiso 1 1 calc R . .
H28B H 1.0598 0.6044 0.2204 0.051 Uiso 1 1 calc R . .
H28C H 1.1768 0.5657 0.1776 0.051 Uiso 1 1 calc R . .
C29 C 0.5383(3) 0.5498(2) 0.22865(11) 0.0295(6) Uani 1 1 d . . .
C30 C 0.8192(4) 0.3365(3) 0.48788(14) 0.0484(9) Uani 1 1 d . . .
C31 C 0.2427(3) 0.8701(2) 0.23717(11) 0.0278(6) Uani 1 1 d . . .
C32 C 0.2540(3) 0.3308(2) 0.06740(11) 0.0270(6) Uani 1 1 d . . .
N1 N 0.5246(2) 0.36152(16) 0.34203(9) 0.0243(5) Uani 1 1 d . . .
N2 N 0.7085(2) 0.46558(15) 0.37598(8) 0.0209(4) Uani 1 1 d . . .
N3 N 0.8902(2) -0.04469(15) 0.34061(8) 0.0215(5) Uani 1 1 d . . .
N4 N 1.0859(2) 0.04501(15) 0.37743(8) 0.0219(5) Uani 1 1 d . . .
N5 N 1.1154(2) -0.01803(15) 0.09998(8) 0.0202(4) Uani 1 1 d . . .
N6 N 1.3194(2) 0.06495(15) 0.13264(8) 0.0193(4) Uani 1 1 d . . .
N7 N 0.7911(2) 0.41334(15) 0.10971(8) 0.0188(4) Uani 1 1 d . . .
N8 N 0.9686(2) 0.50733(15) 0.15632(8) 0.0211(4) Uani 1 1 d . . .
O1 O 0.8011(2) 0.52423(14) 0.26153(8) 0.0331(5) Uani 1 1 d . . .
O2 O 0.7634(3) 0.67453(16) 0.23010(9) 0.0432(5) Uani 1 1 d . . .
O3 O 0.6677(3) 0.64940(17) 0.31473(8) 0.0450(6) Uani 1 1 d . . .
O4 O 0.9871(2) 0.31194(16) 0.41063(8) 0.0389(5) Uani 1 1 d . . .
O5 O 0.9268(3) 0.17712(15) 0.45590(9) 0.0431(5) Uani 1 1 d . . .
O6 O 1.0931(3) 0.31597(19) 0.49964(10) 0.0550(7) Uani 1 1 d . . .
O7 O 0.4094(2) 0.96429(16) 0.31699(8) 0.0375(5) Uani 1 1 d . . .
O8 O 0.4881(2) 0.96734(15) 0.22702(8) 0.0350(5) Uani 1 1 d . . .
O9 O 0.2840(2) 1.05934(13) 0.26195(8) 0.0289(4) Uani 1 1 d . . .
O10 O 0.4275(2) 0.19545(14) 0.03932(8) 0.0312(4) Uani 1 1 d . . .
O11 O 0.1653(2) 0.14631(13) 0.03749(7) 0.0261(4) Uani 1 1 d . . .
O12 O 0.2619(2) 0.23489(14) -0.02882(7) 0.0301(4) Uani 1 1 d . . .
F1 F 0.4753(2) 0.48213(13) 0.25314(8) 0.0450(5) Uani 1 1 d . . .
F2 F 0.5572(2) 0.50549(14) 0.17827(7) 0.0454(5) Uani 1 1 d . . .
F3 F 0.4425(2) 0.61643(14) 0.22673(8) 0.0459(5) Uani 1 1 d . . .
F4 F 0.6969(2) 0.31468(18) 0.45675(10) 0.0648(6) Uani 1 1 d . . .
F5 F 0.7856(3) 0.31477(18) 0.53527(9) 0.0710(7) Uani 1 1 d . . .
F6 F 0.8415(3) 0.43675(15) 0.49764(9) 0.0703(7) Uani 1 1 d . . .
F7 F 0.1931(2) 0.87093(12) 0.18753(7) 0.0391(4) Uani 1 1 d . . .
F8 F 0.1255(2) 0.86577(13) 0.26697(8) 0.0422(4) Uani 1 1 d . . .
F9 F 0.3071(2) 0.78684(12) 0.23567(7) 0.0402(4) Uani 1 1 d . . .
F10 F 0.2713(2) 0.32616(12) 0.11944(6) 0.0365(4) Uani 1 1 d . . .
F11 F 0.11916(19) 0.35923(13) 0.05983(7) 0.0389(4) Uani 1 1 d . . .
F12 F 0.35210(19) 0.40200(11) 0.05884(7) 0.0351(4) Uani 1 1 d . . .
P1 P 0.80971(7) 0.31576(5) 0.30191(3) 0.01905(14) Uani 1 1 d . . .
P2 P 0.96854(7) 0.13132(5) 0.29839(3) 0.01947(14) Uani 1 1 d . . .
P3 P 1.08603(7) 0.14430(5) 0.18778(2) 0.01771(13) Uani 1 1 d . . .
P4 P 0.92948(7) 0.33249(5) 0.19320(3) 0.01818(14) Uani 1 1 d . . .
S1 S 0.75477(7) 0.17280(5) 0.31770(3) 0.02353(14) Uani 1 1 d . . .
S2 S 0.93667(7) 0.04649(5) 0.21917(2) 0.02079(13) Uani 1 1 d . . .
S3 S 0.95346(7) 0.20523(5) 0.13420(2) 0.02220(14) Uani 1 1 d . . .
S4 S 0.71910(7) 0.30181(5) 0.22223(2) 0.02080(13) Uani 1 1 d . . .
S5 S 0.71275(8) 0.60619(5) 0.26263(3) 0.02886(16) Uani 1 1 d . . .
S6 S 0.97498(8) 0.27977(5) 0.46061(3) 0.02987(16) Uani 1 1 d . . .
S7 S 0.37089(8) 0.97733(5) 0.26375(3) 0.02577(15) Uani 1 1 d . . .
S8 S 0.27963(7) 0.21321(5) 0.02380(2) 0.02077(13) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C33 N9 1.130(6) . ?
C33 C34 1.440(6) . ?
C34 H34A 0.9800 . ?
C34 H34B 0.9800 . ?
C34 H34C 0.9800 . ?
C35 N10 1.156(5) . ?
C35 C36 1.441(6) . ?
C36 H36A 0.9800 . ?
C36 H36B 0.9800 . ?
C36 H36C 0.9800 . ?
C37 N11 1.138(5) . ?
C37 C38 1.454(5) . ?
C38 H38A 0.9800 . ?
C38 H38B 0.9800 . ?
C38 H38C 0.9800 . ?
C1 N2 1.343(3) . ?
C1 N1 1.353(3) . ?
C1 P1 1.820(3) . ?
C2 C3 1.355(4) . ?
C2 N1 1.384(3) . ?
C2 C4 1.490(4) . ?
C3 N2 1.373(3) . ?
C3 C5 1.492(4) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 N1 1.455(3) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 N2 1.475(3) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 N3 1.348(3) . ?
C8 N4 1.355(3) . ?
C8 P2 1.822(3) . ?
C9 C10 1.360(4) . ?
C9 N3 1.385(3) . ?
C9 C11 1.487(4) . ?
C10 N4 1.374(3) . ?
C10 C12 1.494(4) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 N3 1.470(3) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 N4 1.467(3) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 N5 1.345(3) . ?
C15 N6 1.348(3) . ?
C15 P3 1.821(2) . ?
C16 C17 1.364(4) . ?
C16 N5 1.377(3) . ?
C16 C18 1.496(4) . ?
C17 N6 1.376(3) . ?
C17 C19 1.489(4) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 N5 1.467(3) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 N6 1.465(3) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 N7 1.345(3) . ?
C22 N8 1.347(3) . ?
C22 P4 1.822(2) . ?
C23 C24 1.363(4) . ?
C23 N7 1.382(3) . ?
C23 C25 1.490(4) . ?
C24 N8 1.379(3) . ?
C24 C26 1.492(4) . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C27 N7 1.463(3) . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C28 N8 1.468(3) . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
C29 F3 1.331(3) . ?
C29 F1 1.331(3) . ?
C29 F2 1.337(3) . ?
C29 S5 1.830(3) . ?
C30 F4 1.327(4) . ?
C30 F5 1.340(4) . ?
C30 F6 1.367(4) . ?
C30 S6 1.777(4) . ?
C31 F7 1.333(3) . ?
C31 F8 1.336(3) . ?
C31 F9 1.336(3) . ?
C31 S7 1.826(3) . ?
C32 F12 1.336(3) . ?
C32 F11 1.341(3) . ?
C32 F10 1.346(3) . ?
C32 S8 1.830(3) . ?
O1 S5 1.446(2) . ?
O2 S5 1.437(2) . ?
O3 S5 1.436(2) . ?
O4 S6 1.435(2) . ?
O5 S6 1.442(2) . ?
O6 S6 1.434(2) . ?
O7 S7 1.440(2) . ?
O8 S7 1.441(2) . ?
O9 S7 1.4487(19) . ?
O10 S8 1.446(2) . ?
O11 S8 1.4385(19) . ?
O12 S8 1.4382(19) . ?
P1 S1 2.1306(9) . ?
P1 S4 2.1364(9) . ?
P2 S1 2.1234(9) . ?
P2 S2 2.1326(9) . ?
P3 S2 2.1314(9) . ?
P3 S3 2.1343(9) . ?
P4 S4 2.1192(9) . ?
P4 S3 2.1232(9) . ?

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
N9 C33 C34 177.5(7) . . ?
C33 C34 H34A 109.5 . . ?
C33 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
C33 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
N10 C35 C36 179.6(4) . . ?
C35 C36 H36A 109.5 . . ?
C35 C36 H36B 109.5 . . ?
H36A C36 H36B 109.5 . . ?
C35 C36 H36C 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
N11 C37 C38 179.4(5) . . ?
C37 C38 H38A 109.5 . . ?
C37 C38 H38B 109.5 . . ?
H38A C38 H38B 109.5 . . ?
C37 C38 H38C 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
N2 C1 N1 107.0(2) . . ?
N2 C1 P1 121.60(19) . . ?
N1 C1 P1 131.44(19) . . ?
C3 C2 N1 106.6(2) . . ?
C3 C2 C4 131.1(3) . . ?
N1 C2 C4 122.2(3) . . ?
C2 C3 N2 107.6(2) . . ?
C2 C3 C5 130.2(3) . . ?
N2 C3 C5 122.3(3) . . ?
C2 C4 H4A 109.5 . . ?
C2 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C2 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C3 C5 H5A 109.5 . . ?
C3 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C3 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
N1 C6 H6A 109.5 . . ?
N1 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
N1 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
N2 C7 H7A 109.5 . . ?
N2 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
N2 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N3 C8 N4 106.8(2) . . ?
N3 C8 P2 132.66(19) . . ?
N4 C8 P2 120.48(19) . . ?
C10 C9 N3 106.9(2) . . ?
C10 C9 C11 130.6(2) . . ?
N3 C9 C11 122.6(2) . . ?
C9 C10 N4 107.3(2) . . ?
C9 C10 C12 130.7(3) . . ?
N4 C10 C12 122.0(2) . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N3 C13 H13A 109.5 . . ?
N3 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
N3 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N4 C14 H14A 109.5 . . ?
N4 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
N4 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N5 C15 N6 106.8(2) . . ?
N5 C15 P3 131.65(19) . . ?
N6 C15 P3 121.50(18) . . ?
C17 C16 N5 107.0(2) . . ?
C17 C16 C18 130.0(3) . . ?
N5 C16 C18 123.0(3) . . ?
C16 C17 N6 106.6(2) . . ?
C16 C17 C19 131.3(3) . . ?
N6 C17 C19 122.0(2) . . ?
C16 C18 H18A 109.5 . . ?
C16 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C16 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C17 C19 H19A 109.5 . . ?
C17 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C17 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
N5 C20 H20A 109.5 . . ?
N5 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
N5 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
N6 C21 H21A 109.5 . . ?
N6 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
N6 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
N7 C22 N8 106.9(2) . . ?
N7 C22 P4 131.45(18) . . ?
N8 C22 P4 121.58(18) . . ?
C24 C23 N7 106.5(2) . . ?
C24 C23 C25 130.9(2) . . ?
N7 C23 C25 122.5(2) . . ?
C23 C24 N8 107.2(2) . . ?
C23 C24 C26 130.3(2) . . ?
N8 C24 C26 122.6(2) . . ?
C23 C25 H25A 109.5 . . ?
C23 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C23 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C24 C26 H26A 109.5 . . ?
C24 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C24 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
N7 C27 H27A 109.5 . . ?
N7 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
N7 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
N8 C28 H28A 109.5 . . ?
N8 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
N8 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
F3 C29 F1 107.5(2) . . ?
F3 C29 F2 107.3(2) . . ?
F1 C29 F2 107.0(2) . . ?
F3 C29 S5 111.4(2) . . ?
F1 C29 S5 111.9(2) . . ?
F2 C29 S5 111.5(2) . . ?
F4 C30 F5 106.4(3) . . ?
F4 C30 F6 105.3(3) . . ?
F5 C30 F6 104.6(3) . . ?
F4 C30 S6 114.5(3) . . ?
F5 C30 S6 113.2(2) . . ?
F6 C30 S6 112.1(2) . . ?
F7 C31 F8 107.3(2) . . ?
F7 C31 F9 107.4(2) . . ?
F8 C31 F9 107.3(2) . . ?
F7 C31 S7 111.62(19) . . ?
F8 C31 S7 111.83(19) . . ?
F9 C31 S7 111.21(19) . . ?
F12 C32 F11 107.7(2) . . ?
F12 C32 F10 106.6(2) . . ?
F11 C32 F10 107.3(2) . . ?
F12 C32 S8 111.50(19) . . ?
F11 C32 S8 111.74(19) . . ?
F10 C32 S8 111.68(18) . . ?
C1 N1 C2 109.3(2) . . ?
C1 N1 C6 126.6(2) . . ?
C2 N1 C6 124.1(2) . . ?
C1 N2 C3 109.6(2) . . ?
C1 N2 C7 125.2(2) . . ?
C3 N2 C7 125.3(2) . . ?
C8 N3 C9 109.5(2) . . ?
C8 N3 C13 126.5(2) . . ?
C9 N3 C13 123.9(2) . . ?
C8 N4 C10 109.6(2) . . ?
C8 N4 C14 126.6(2) . . ?
C10 N4 C14 123.8(2) . . ?
C15 N5 C16 109.6(2) . . ?
C15 N5 C20 126.2(2) . . ?
C16 N5 C20 124.1(2) . . ?
C15 N6 C17 109.8(2) . . ?
C15 N6 C21 126.8(2) . . ?
C17 N6 C21 123.3(2) . . ?
C22 N7 C23 109.8(2) . . ?
C22 N7 C27 126.6(2) . . ?
C23 N7 C27 123.5(2) . . ?
C22 N8 C24 109.5(2) . . ?
C22 N8 C28 126.7(2) . . ?
C24 N8 C28 123.7(2) . . ?
C1 P1 S1 99.31(8) . . ?
C1 P1 S4 101.26(9) . . ?
S1 P1 S4 101.99(4) . . ?
C8 P2 S1 98.30(9) . . ?
C8 P2 S2 102.39(8) . . ?
S1 P2 S2 103.63(4) . . ?
C15 P3 S2 101.12(8) . . ?
C15 P3 S3 97.37(8) . . ?
S2 P3 S3 104.79(4) . . ?
C22 P4 S4 102.37(8) . . ?
C22 P4 S3 99.62(8) . . ?
S4 P4 S3 102.97(4) . . ?
P2 S1 P1 91.11(4) . . ?
P3 S2 P2 92.54(3) . . ?
P4 S3 P3 92.15(3) . . ?
P4 S4 P1 91.76(3) . . ?
O3 S5 O2 115.48(14) . . ?
O3 S5 O1 114.79(13) . . ?
O2 S5 O1 114.63(14) . . ?
O3 S5 C29 102.35(14) . . ?
O2 S5 C29 103.38(13) . . ?
O1 S5 C29 103.80(12) . . ?
O6 S6 O4 115.59(15) . . ?
O6 S6 O5 114.79(15) . . ?
O4 S6 O5 114.73(14) . . ?
O6 S6 C30 104.76(17) . . ?
O4 S6 C30 102.93(14) . . ?
O5 S6 C30 101.52(16) . . ?
O7 S7 O8 115.21(13) . . ?
O7 S7 O9 114.26(12) . . ?
O8 S7 O9 115.16(12) . . ?
O7 S7 C31 103.38(13) . . ?
O8 S7 C31 102.98(13) . . ?
O9 S7 C31 103.54(12) . . ?
O12 S8 O11 114.94(11) . . ?
O12 S8 O10 115.23(12) . . ?
O11 S8 O10 114.73(12) . . ?
O12 S8 C32 102.68(12) . . ?
O11 S8 C32 104.19(12) . . ?
O10 S8 C32 102.64(12) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        27.88
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         1.374
_refine_diff_density_min         -0.821
_refine_diff_density_rms         0.078
####################################################################### 
# 
# 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_added_by_encifer
_database_code_depnum_ccdc_archive 'CCDC 1424342'
_audit_update_record             
;
2015-09-14 deposited with the CCDC.
2015-11-17 downloaded from the CCDC.
;
_audit_creation_date             2015-09-07
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H20 N4 P S2, C F3 O3 S'
_chemical_formula_sum            'C15 H20 F3 N4 O3 P S3'
_chemical_formula_weight         488.50
_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'
F F 0.0171 0.0103 '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      monoclinic
_space_group_IT_number           11
_space_group_name_H-M_alt        'P 1 21/m 1'
_space_group_name_Hall           '-P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'
'-x, -y, -z'
'x, -y-1/2, z'

_cell_length_a                   6.5855(4)
_cell_length_b                   12.5308(6)
_cell_length_c                   12.4698(7)
_cell_angle_alpha                90
_cell_angle_beta                 91.568(2)
_cell_angle_gamma                90
_cell_volume                     1028.64(10)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4744
_cell_measurement_temperature    153
_cell_measurement_theta_max      29.476
_cell_measurement_theta_min      2.304
_shelx_estimated_absorpt_T_max   0.911
_shelx_estimated_absorpt_T_min   0.852
_exptl_absorpt_coefficient_mu    0.490
_exptl_absorpt_correction_T_max  0.7459
_exptl_absorpt_correction_T_min  0.7001
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0611 before and 0.0288 after correction.
The Ratio of minimum to maximum transmission is 0.9386.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.577
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.338
_exptl_crystal_size_mid          0.236
_exptl_crystal_size_min          0.194
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0158
_diffrn_reflns_av_unetI/netI     0.0189
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.869
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            8389
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.869
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         29.529
_diffrn_reflns_theta_min         2.305
_diffrn_ambient_temperature      153
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.869
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2345
_reflns_number_total             2607
_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  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         1.102
_refine_diff_density_min         -0.403
_refine_diff_density_rms         0.071
_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     144
_refine_ls_number_reflns         2607
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0406
_refine_ls_R_factor_gt           0.0369
_refine_ls_restrained_S_all      1.061
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0582P)²+0.7676P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1027
_refine_ls_wR_factor_ref         0.1055
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C5(H5), C2(H2), C4(H4)
2.b Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C7(H7A,H7B,H7C)
;
_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
P1 P 0.48697(9) 0.2500 0.45344(5) 0.01582(15) Uani 1 2 d S T P . .
S1 S 0.77276(9) 0.2500 0.42265(5) 0.02213(16) Uani 1 2 d S T P . .
S3 S -0.09108(10) 0.2500 0.86247(5) 0.02430(16) Uani 1 2 d S T P . .
S2 S 0.27385(10) 0.2500 0.34414(5) 0.02233(16) Uani 1 2 d S T P . .
F2 F 0.1696(3) 0.2500 1.02539(14) 0.0453(5) Uani 1 2 d S T P . .
N1 N 0.4387(2) 0.35539(11) 0.54608(11) 0.0167(3) Uani 1 1 d . . . . .
F1 F 0.2679(3) 0.33556(15) 0.89084(16) 0.0712(6) Uani 1 1 d . . . . .
N2 N 0.3133(2) 0.55446(12) 0.80079(11) 0.0213(3) Uani 1 1 d . . . . .
O1 O -0.0669(4) 0.2500 0.74946(16) 0.0447(6) Uani 1 2 d S T P . .
O2 O -0.1747(3) 0.34621(18) 0.90531(15) 0.0600(6) Uani 1 1 d . . . . .
C3 C 0.3542(3) 0.49407(13) 0.71668(13) 0.0186(3) Uani 1 1 d . . . . .
C1 C 0.5886(3) 0.38768(15) 0.61667(14) 0.0209(3) Uani 1 1 d . . . . .
H1 H 0.7227 0.3617 0.6079 0.025 Uiso 1 1 calc R . . . .
C5 C 0.2470(3) 0.39338(14) 0.55972(14) 0.0214(4) Uani 1 1 d . . . . .
H5 H 0.1415 0.3716 0.5110 0.026 Uiso 1 1 calc R . . . .
C2 C 0.5531(3) 0.45542(14) 0.69870(14) 0.0221(4) Uani 1 1 d . . . . .
H2 H 0.6626 0.4773 0.7448 0.027 Uiso 1 1 calc R . . . .
C4 C 0.2019(3) 0.46105(15) 0.64036(14) 0.0231(4) Uani 1 1 d . . . . .
H4 H 0.0670 0.4868 0.6461 0.028 Uiso 1 1 calc R . . . .
C8 C 0.1681(4) 0.2500 0.9178(2) 0.0255(5) Uani 1 2 d S T P . .
C6 C 0.4750(3) 0.58724(17) 0.87681(14) 0.0292(4) Uani 1 1 d . . . . .
H6A H 0.5485 0.5240 0.9030 0.044 Uiso 1 1 calc GR . . . .
H6B H 0.4153 0.6246 0.9374 0.044 Uiso 1 1 calc GR . . . .
H6C H 0.5692 0.6351 0.8409 0.044 Uiso 1 1 calc GR . . . .
C7 C 0.1056(3) 0.58731(18) 0.82266(16) 0.0324(4) Uani 1 1 d . . . . .
H7A H 0.0519 0.6304 0.7628 0.049 Uiso 1 1 calc GR . . . .
H7B H 0.1053 0.6296 0.8887 0.049 Uiso 1 1 calc GR . . . .
H7C H 0.0204 0.5239 0.8311 0.049 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
P1 S1 1.9311(9) . ?
P1 S2 1.9294(8) . ?
P1 N1 1.7888(14) 4_565 ?
P1 N1 1.7888(14) . ?
S3 O1 1.422(2) . ?
S3 O2 1.4345(19) 4_565 ?
S3 O2 1.4345(19) . ?
S3 C8 1.824(3) . ?
F2 C8 1.341(3) . ?
N1 C1 1.366(2) . ?
N1 C5 1.364(2) . ?
F1 C8 1.307(2) . ?
N2 C3 1.327(2) . ?
N2 C6 1.465(2) . ?
N2 C7 1.461(2) . ?
C3 C2 1.420(2) . ?
C3 C4 1.425(2) . ?
C1 H1 0.9500 . ?
C1 C2 1.354(2) . ?
C5 H5 0.9500 . ?
C5 C4 1.355(2) . ?
C2 H2 0.9500 . ?
C4 H4 0.9500 . ?
C8 F1 1.306(2) 4_565 ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 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
S2 P1 S1 123.62(4) . . ?
N1 P1 S1 108.65(5) 4_565 . ?
N1 P1 S1 108.65(5) . . ?
N1 P1 S2 108.51(5) 4_565 . ?
N1 P1 S2 108.51(5) . . ?
N1 P1 N1 95.17(9) . 4_565 ?
O1 S3 O2 115.05(10) . . ?
O1 S3 O2 115.05(10) . 4_565 ?
O1 S3 C8 104.25(14) . . ?
O2 S3 O2 114.4(2) 4_565 . ?
O2 S3 C8 102.93(9) . . ?
O2 S3 C8 102.93(9) 4_565 . ?
C1 N1 P1 119.79(12) . . ?
C5 N1 P1 121.30(12) . . ?
C5 N1 C1 118.12(14) . . ?
C3 N2 C6 120.77(15) . . ?
C3 N2 C7 121.31(15) . . ?
C7 N2 C6 117.88(15) . . ?
N2 C3 C2 121.84(16) . . ?
N2 C3 C4 122.60(16) . . ?
C2 C3 C4 115.53(15) . . ?
N1 C1 H1 118.8 . . ?
C2 C1 N1 122.38(16) . . ?
C2 C1 H1 118.8 . . ?
N1 C5 H5 118.9 . . ?
C4 C5 N1 122.23(16) . . ?
C4 C5 H5 118.9 . . ?
C3 C2 H2 119.6 . . ?
C1 C2 C3 120.80(16) . . ?
C1 C2 H2 119.6 . . ?
C3 C4 H4 119.6 . . ?
C5 C4 C3 120.86(16) . . ?
C5 C4 H4 119.6 . . ?
F2 C8 S3 111.08(19) . . ?
F1 C8 S3 112.02(14) 4_565 . ?
F1 C8 S3 112.02(14) . . ?
F1 C8 F2 105.53(17) 4_565 . ?
F1 C8 F2 105.53(17) . . ?
F1 C8 F1 110.3(3) 4_565 . ?
N2 C6 H6A 109.5 . . ?
N2 C6 H6B 109.5 . . ?
N2 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
N2 C7 H7A 109.5 . . ?
N2 C7 H7B 109.5 . . ?
N2 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 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
P1 N1 C1 C2 -169.98(14) . . . . ?
P1 N1 C5 C4 169.63(14) . . . . ?
S1 P1 N1 C1 -28.60(14) . . . . ?
S1 P1 N1 C5 161.77(12) . . . . ?
S2 P1 N1 C1 -165.42(12) . . . . ?
S2 P1 N1 C5 24.95(14) . . . . ?
N1 P1 N1 C1 83.08(14) 4_565 . . . ?
N1 P1 N1 C5 -86.55(14) 4_565 . . . ?
N1 C1 C2 C3 1.7(3) . . . . ?
N1 C5 C4 C3 -1.3(3) . . . . ?
N2 C3 C2 C1 175.21(17) . . . . ?
N2 C3 C4 C5 -175.38(17) . . . . ?
O1 S3 C8 F2 180.000(1) . . . . ?
O1 S3 C8 F1 62.27(18) . . . . ?
O1 S3 C8 F1 -62.27(18) . . . 4_565 ?
O2 S3 C8 F2 59.57(10) . . . . ?
O2 S3 C8 F2 -59.57(10) 4_565 . . . ?
O2 S3 C8 F1 177.30(19) . . . 4_565 ?
O2 S3 C8 F1 58.2(2) 4_565 . . 4_565 ?
O2 S3 C8 F1 -58.2(2) . . . . ?
O2 S3 C8 F1 -177.30(19) 4_565 . . . ?
C1 N1 C5 C4 -0.2(3) . . . . ?
C5 N1 C1 C2 0.0(3) . . . . ?
C2 C3 C4 C5 2.8(3) . . . . ?
C4 C3 C2 C1 -3.0(3) . . . . ?
C6 N2 C3 C2 2.4(3) . . . . ?
C6 N2 C3 C4 -179.52(17) . . . . ?
C7 N2 C3 C2 -175.50(17) . . . . ?
C7 N2 C3 C4 2.6(3) . . . . ?

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

data_added_by_encifer
_database_code_depnum_ccdc_archive 'CCDC 1424343'
_audit_update_record             
;
2015-09-14 deposited with the CCDC.
2015-11-17 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H20 F3 N4 O3 P S3 '
_chemical_formula_sum            'C15 H20 F3 N4 O3 P S3'
_chemical_formula_weight         488.50

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'
F F 0.0171 0.0103 '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'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.3991(6)
_cell_length_b                   10.1015(7)
_cell_length_c                   13.5475(9)
_cell_angle_alpha                69.1580(10)
_cell_angle_beta                 78.1620(10)
_cell_angle_gamma                84.5940(10)
_cell_volume                     1051.08(13)
_cell_formula_units_Z            2
_cell_measurement_temperature    153(2)
_cell_measurement_reflns_used    900
_cell_measurement_theta_min      1
_cell_measurement_theta_max      22.5

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.544
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             504
_exptl_absorpt_coefficient_mu    0.480
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9359
_exptl_absorpt_correction_T_max  0.9858
_exptl_absorpt_process_details   
; 
 Corrections were done with the SADABS program, utilizing the none merged
 raw data obtained from the integration process. Integration and final cell
 refinement were done with SAINT.

 SADABS reports ratio of Tmin/Tmax =  0.92356

;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      153(1)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'Omega and Phi scans'
_diffrn_detector_area_resol_mean 80
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10111
_diffrn_reflns_av_R_equivalents  0.0241
_diffrn_reflns_av_sigmaI/netI    0.0388
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.64
_diffrn_reflns_theta_max         27.88
_reflns_number_total             4929
_reflns_number_gt                3819
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2(Bruker AXS, 2007)'
_computing_cell_refinement       'APEX2(Bruker AXS, 2007)'
_computing_data_reduction        'SAINT,SADABS (Bruker AXS, 2007 )'
_computing_structure_solution    
;
SHELXS-97 , G. M. Sheldrick, Acta Cryst. (2008) A64, 112-122
;
_computing_structure_refinement  
;
SHELXL-97, G. M. Sheldrick, Acta Cryst. (2008) A64, 112-122
;
_computing_molecular_graphics    
;
ORTEP3,L.J. Farrugia, J. Appl. Cryst. (1997) 30, 565
;
_computing_publication_material  ?

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0448P)²+0.6336P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    noref
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4929
_refine_ls_number_parameters     266
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0568
_refine_ls_R_factor_gt           0.0412
_refine_ls_wR_factor_ref         0.1064
_refine_ls_wR_factor_gt          0.0975
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.029
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.4562(3) 0.1520(2) 0.86244(17) 0.0273(5) Uani 1 1 d . . .
H1 H 0.4395 0.1121 0.8117 0.033 Uiso 1 1 calc R . .
C2 C 0.3254(3) 0.1945(2) 0.92134(18) 0.0282(5) Uani 1 1 d . . .
H2 H 0.2194 0.1826 0.9118 0.034 Uiso 1 1 calc R . .
C3 C 0.3435(3) 0.2570(2) 0.99739(16) 0.0260(4) Uani 1 1 d . . .
C4 C 0.5064(3) 0.2620(2) 1.01099(17) 0.0288(5) Uani 1 1 d . . .
H4 H 0.5266 0.2971 1.0635 0.035 Uiso 1 1 calc R . .
C5 C 0.6324(3) 0.2173(2) 0.94993(17) 0.0277(5) Uani 1 1 d . . .
H5 H 0.7396 0.2228 0.9605 0.033 Uiso 1 1 calc R . .
C6 C 0.0526(3) 0.3070(3) 1.0306(2) 0.0365(5) Uani 1 1 d . . .
H6A H 0.0501 0.3608 0.9548 0.055 Uiso 1 1 calc R . .
H6B H -0.0239 0.3506 1.0759 0.055 Uiso 1 1 calc R . .
H6C H 0.0216 0.2091 1.0477 0.055 Uiso 1 1 calc R . .
C7 C 0.2401(3) 0.3768(3) 1.1251(2) 0.0388(6) Uani 1 1 d . . .
H7A H 0.2963 0.3110 1.1806 0.058 Uiso 1 1 calc R . .
H7B H 0.1338 0.4042 1.1590 0.058 Uiso 1 1 calc R . .
H7C H 0.3054 0.4614 1.0855 0.058 Uiso 1 1 calc R . .
C8 C 0.8814(3) 0.4042(2) 0.69913(17) 0.0271(5) Uani 1 1 d . . .
H8 H 0.9357 0.3790 0.7585 0.033 Uiso 1 1 calc R . .
C9 C 0.8866(3) 0.5400(2) 0.63104(17) 0.0260(4) Uani 1 1 d . . .
H9 H 0.9449 0.6072 0.6431 0.031 Uiso 1 1 calc R . .
C10 C 0.8060(3) 0.5835(2) 0.54158(17) 0.0258(4) Uani 1 1 d . . .
C11 C 0.7313(3) 0.4731(2) 0.52613(17) 0.0270(5) Uani 1 1 d . . .
H11 H 0.6820 0.4936 0.4650 0.032 Uiso 1 1 calc R . .
C12 C 0.7300(3) 0.3398(2) 0.59753(17) 0.0277(5) Uani 1 1 d . . .
H12 H 0.6772 0.2690 0.5858 0.033 Uiso 1 1 calc R . .
C13 C 0.8756(3) 0.8305(3) 0.4942(2) 0.0406(6) Uani 1 1 d . . .
H13A H 0.8049 0.8538 0.5533 0.061 Uiso 1 1 calc R . .
H13B H 0.8874 0.9147 0.4289 0.061 Uiso 1 1 calc R . .
H13C H 0.9827 0.7988 0.5131 0.061 Uiso 1 1 calc R . .
C14 C 0.7088(3) 0.7622(3) 0.3888(2) 0.0439(6) Uani 1 1 d . . .
H14A H 0.7277 0.6945 0.3506 0.066 Uiso 1 1 calc R . .
H14B H 0.7426 0.8564 0.3387 0.066 Uiso 1 1 calc R . .
H14C H 0.5928 0.7656 0.4194 0.066 Uiso 1 1 calc R . .
C15 C 1.3291(4) -0.2327(3) 0.6751(2) 0.0507(7) Uani 1 1 d . . .
N1 N 0.6120(2) 0.16414(18) 0.87328(14) 0.0239(4) Uani 1 1 d . . .
N2 N 0.2173(2) 0.3077(2) 1.05088(15) 0.0299(4) Uani 1 1 d . . .
N3 N 0.8013(2) 0.30207(19) 0.68581(14) 0.0244(4) Uani 1 1 d . . .
N4 N 0.8033(2) 0.7174(2) 0.47532(15) 0.0316(4) Uani 1 1 d . . .
O1 O 1.1551(2) -0.4524(2) 0.76117(16) 0.0515(5) Uani 1 1 d . . .
O2 O 1.4351(3) -0.4820(3) 0.68999(19) 0.0662(6) Uani 1 1 d . . .
O3 O 1.3570(3) -0.4242(2) 0.85387(15) 0.0497(5) Uani 1 1 d . . .
F1 F 1.2872(3) -0.2033(2) 0.57994(14) 0.0831(7) Uani 1 1 d . . .
F2 F 1.4803(3) -0.1864(3) 0.6543(2) 0.1079(9) Uani 1 1 d . . .
F3 F 1.2368(4) -0.1543(2) 0.72356(17) 0.1074(10) Uani 1 1 d . . .
P1 P 0.78220(7) 0.12621(6) 0.78385(5) 0.02601(14) Uani 1 1 d . . .
S1 S 0.71358(8) 0.00444(6) 0.71897(5) 0.03506(15) Uani 1 1 d . . .
S2 S 0.96814(7) 0.08645(7) 0.85433(5) 0.03521(15) Uani 1 1 d . . .
S3 S 1.31959(7) -0.41915(6) 0.75453(5) 0.02878(14) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.351(3) . ?
C1 N1 1.367(3) . ?
C1 H1 0.9500 . ?
C2 C3 1.424(3) . ?
C2 H2 0.9500 . ?
C3 N2 1.326(3) . ?
C3 C4 1.426(3) . ?
C4 C5 1.351(3) . ?
C4 H4 0.9500 . ?
C5 N1 1.372(3) . ?
C5 H5 0.9500 . ?
C6 N2 1.465(3) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 N2 1.462(3) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 C9 1.352(3) . ?
C8 N3 1.365(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.422(3) . ?
C9 H9 0.9500 . ?
C10 N4 1.332(3) . ?
C10 C11 1.426(3) . ?
C11 C12 1.349(3) . ?
C11 H11 0.9500 . ?
C12 N3 1.364(3) . ?
C12 H12 0.9500 . ?
C13 N4 1.464(3) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 N4 1.464(3) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 F3 1.306(4) . ?
C15 F1 1.330(3) . ?
C15 F2 1.335(4) . ?
C15 S3 1.807(3) . ?
N1 P1 1.7820(18) . ?
N3 P1 1.7980(19) . ?
O1 S3 1.4294(18) . ?
O2 S3 1.428(2) . ?
O3 S3 1.4263(17) . ?
P1 S1 1.9309(8) . ?
P1 S2 1.9321(8) . ?

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 C1 N1 122.4(2) . . ?
C2 C1 H1 118.8 . . ?
N1 C1 H1 118.8 . . ?
C1 C2 C3 121.2(2) . . ?
C1 C2 H2 119.4 . . ?
C3 C2 H2 119.4 . . ?
N2 C3 C2 122.1(2) . . ?
N2 C3 C4 122.7(2) . . ?
C2 C3 C4 115.25(19) . . ?
C5 C4 C3 120.7(2) . . ?
C5 C4 H4 119.6 . . ?
C3 C4 H4 119.6 . . ?
C4 C5 N1 122.7(2) . . ?
C4 C5 H5 118.6 . . ?
N1 C5 H5 118.6 . . ?
N2 C6 H6A 109.5 . . ?
N2 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
N2 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
N2 C7 H7A 109.5 . . ?
N2 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
N2 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C9 C8 N3 122.5(2) . . ?
C9 C8 H8 118.7 . . ?
N3 C8 H8 118.7 . . ?
C8 C9 C10 120.9(2) . . ?
C8 C9 H9 119.5 . . ?
C10 C9 H9 119.5 . . ?
N4 C10 C9 122.5(2) . . ?
N4 C10 C11 122.2(2) . . ?
C9 C10 C11 115.3(2) . . ?
C12 C11 C10 120.6(2) . . ?
C12 C11 H11 119.7 . . ?
C10 C11 H11 119.7 . . ?
C11 C12 N3 122.9(2) . . ?
C11 C12 H12 118.5 . . ?
N3 C12 H12 118.5 . . ?
N4 C13 H13A 109.5 . . ?
N4 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
N4 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N4 C14 H14A 109.5 . . ?
N4 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
N4 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
F3 C15 F1 107.5(3) . . ?
F3 C15 F2 106.5(3) . . ?
F1 C15 F2 105.8(3) . . ?
F3 C15 S3 112.7(2) . . ?
F1 C15 S3 113.0(2) . . ?
F2 C15 S3 110.9(2) . . ?
C1 N1 C5 117.58(18) . . ?
C1 N1 P1 121.13(14) . . ?
C5 N1 P1 121.09(15) . . ?
C3 N2 C7 120.9(2) . . ?
C3 N2 C6 120.97(19) . . ?
C7 N2 C6 117.93(19) . . ?
C12 N3 C8 117.57(19) . . ?
C12 N3 P1 120.98(15) . . ?
C8 N3 P1 121.40(15) . . ?
C10 N4 C13 121.6(2) . . ?
C10 N4 C14 121.6(2) . . ?
C13 N4 C14 116.2(2) . . ?
N1 P1 N3 96.77(8) . . ?
N1 P1 S1 108.69(6) . . ?
N3 P1 S1 107.97(6) . . ?
N1 P1 S2 107.84(6) . . ?
N3 P1 S2 108.05(7) . . ?
S1 P1 S2 124.09(4) . . ?
O3 S3 O2 117.46(14) . . ?
O3 S3 O1 114.23(13) . . ?
O2 S3 O1 113.21(13) . . ?
O3 S3 C15 103.23(12) . . ?
O2 S3 C15 103.03(14) . . ?
O1 S3 C15 103.24(14) . . ?

_diffrn_measured_fraction_theta_max 0.985
_diffrn_reflns_theta_full        27.88
_diffrn_measured_fraction_theta_full 0.985
_refine_diff_density_max         0.528
_refine_diff_density_min         -0.342
_refine_diff_density_rms         0.061
####################################################################### 
# 
# 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_added_by_encifer
_database_code_depnum_ccdc_archive 'CCDC 1426199'
_audit_update_record             
;
2015-09-21 deposited with the CCDC.
2015-11-17 downloaded from the CCDC.
;
_audit_creation_date             2015-09-21
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C44 H80 N8 P4 S4, 4(C F3 O3 S)'
_chemical_formula_sum            'C48 H80 F12 N8 O12 P4 S8'
_chemical_formula_weight         1569.56
_chemical_absolute_configuration .
_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'
F F 0.0171 0.0103 '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      tetragonal
_space_group_IT_number           79
_space_group_name_H-M_alt        'I 4'
_space_group_name_Hall           'I 4'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x, z'
'-x, -y, z'
'y, -x, z'
'x+1/2, y+1/2, z+1/2'
'-y+1/2, x+1/2, z+1/2'
'-x+1/2, -y+1/2, z+1/2'
'y+1/2, -x+1/2, z+1/2'

_cell_length_a                   17.5055(4)
_cell_length_b                   17.5055(4)
_cell_length_c                   13.3734(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4098.2(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    ?
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      ?
_cell_measurement_theta_min      ?
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.374
_exptl_absorpt_correction_T_max  0.93618
_exptl_absorpt_correction_T_min  0.93618
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.272
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1632
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0264
_diffrn_reflns_av_unetI/netI     0.0226
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            18047
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         28.281
_diffrn_reflns_theta_min         1.645
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.919
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                4006
_reflns_number_total             5071
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         1.052
_refine_diff_density_min         -0.282
_refine_diff_density_rms         0.085
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.32(18)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     378
_refine_ls_number_reflns         5071
_refine_ls_number_restraints     523
_refine_ls_R_factor_all          0.0784
_refine_ls_R_factor_gt           0.0623
_refine_ls_restrained_S_all      1.097
_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)+(0.1052P)²+3.3272P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1627
_refine_ls_wR_factor_ref         0.1761
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.68(18) 0.32(18)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All C(H,H,H,H,H,H) groups
3. Restrained distances
 C2A-C4A \\sim C4B-C2B \\sim C5B-C3B \\sim C5A-C3A
 with sigma of 0.02
4. Uiso/Uaniso restraints and constraints
C12A \\sim S2 \\sim O2B \\sim O3A \\sim O1B \\sim O2A \\sim O1A \\sim O3B \\sim
C12B \\sim F2A \\sim F1A \\sim F3A \\sim F2B \\sim F3B \\sim F1B: within 2A
with sigma of 0.01 and sigma for terminal atoms of 0.02
N1B \\sim C1B \\sim N2B \\sim C2B \\sim C6B \\sim C3B \\sim C9B \\sim C4B \\sim
C7 \\sim C8 \\sim C5B \\sim C11 \\sim C10 \\sim C6A \\sim C9A \\sim N1A \\sim
N2A \\sim C1A \\sim C2A \\sim C3A \\sim C4A \\sim C5A: within 2A with sigma of
0.01 and sigma for terminal atoms of 0.02
5. Others
 Sof(P1B)=Sof(C3B)=Sof(N1B)=Sof(C2B)=Sof(N2B)=Sof(H10D)=Sof(H10E)=Sof(H10F)=
 Sof(H7BD)=Sof(H7BE)=Sof(H7BF)=Sof(H8BD)=Sof(H8BE)=Sof(H8BF)=Sof(C5B)=Sof(H5BA)=
 Sof(H5BB)=Sof(H5BC)=Sof(H11D)=Sof(H11E)=Sof(H11F)=Sof(C9B)=Sof(H9B)=Sof(C6B)=
 Sof(H6B)=Sof(S1B)=Sof(C1B)=Sof(C4B)=Sof(H4BA)=Sof(H4BB)=Sof(H4BC)=1-FVAR(1)
 Sof(P1A)=Sof(S1A)=Sof(C1A)=Sof(H10A)=Sof(H10B)=Sof(H10C)=Sof(H7AA)=Sof(H7AB)=
 Sof(H7AC)=Sof(H8AA)=Sof(H8AB)=Sof(H8AC)=Sof(H11A)=Sof(H11B)=Sof(H11C)=Sof(C4A)=
 Sof(H4AA)=Sof(H4AB)=Sof(H4AC)=Sof(N2A)=Sof(N1A)=Sof(C3A)=Sof(C2A)=Sof(C9A)=
 Sof(H9A)=Sof(C6A)=Sof(H6A)=Sof(C5A)=Sof(H5AA)=Sof(H5AB)=Sof(H5AC)=FVAR(1)
 Sof(O1B)=Sof(O3B)=Sof(F2B)=Sof(F3B)=Sof(F1B)=Sof(C12B)=Sof(O2B)=1-FVAR(2)
 Sof(O2A)=Sof(C12A)=Sof(F2A)=Sof(F1A)=Sof(F3A)=Sof(O3A)=Sof(O1A)=FVAR(2)
6.a Ternary CH refined with riding coordinates:
 C9B(H9B), C6B(H6B), C9A(H9A), C6A(H6A)
6.b Me refined with riding coordinates:
 C10(H10D,H10E,H10F), C10(H10A,H10B,H10C), C7(H7BD,H7BE,H7BF), C7(H7AA,H7AB,
 H7AC), C8(H8BD,H8BE,H8BF), C8(H8AA,H8AB,H8AC)
6.c Idealised Me refined as rotating group:
 C5B(H5BA,H5BB,H5BC), C11(H11D,H11E,H11F), C11(H11A,H11B,H11C), C4A(H4AA,H4AB,
 H4AC), C5A(H5AA,H5AB,H5AC), C4B(H4BA,H4BB,H4BC)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
P1B P 0.55097(15) 0.38312(16) 0.3448(2) 0.0200(8) Uani 0.428(4) 1 d . . P A 2
S2 S 0.67475(6) -0.14204(7) 0.2968(2) 0.0536(3) Uani 1 1 d . U . . .
P1A P 0.55097(12) 0.38357(11) 0.24844(19) 0.0251(7) Uani 0.572(4) 1 d . . P A 1
S1A S 0.44999(14) 0.37304(18) 0.3361(2) 0.0419(9) Uani 0.572(4) 1 d . . P A 1
C3B C 0.6489(11) 0.1756(15) 0.345(2) 0.035(3) Uani 0.428(4) 1 d D U P A 2
N1B N 0.6033(9) 0.2550(9) 0.2268(12) 0.029(2) Uani 0.428(4) 1 d . U P A 2
C2B C 0.6356(17) 0.1878(12) 0.2343(17) 0.034(3) Uani 0.428(4) 1 d D U P A 2
N2B N 0.6185(10) 0.2418(10) 0.3847(14) 0.032(3) Uani 0.428(4) 1 d . U P A 2
C1A C 0.5941(7) 0.2897(8) 0.2750(10) 0.0249(18) Uani 0.572(4) 1 d . U P A 1
C10 C 0.5289(4) 0.2491(5) 0.5307(6) 0.0634(19) Uani 1 1 d . U . . .
H10D H 0.5076 0.2031 0.4998 0.095 Uiso 0.428(4) 1 calc R . P A 2
H10E H 0.5245 0.2453 0.6036 0.095 Uiso 0.428(4) 1 calc R . P A 2
H10F H 0.5007 0.2940 0.5073 0.095 Uiso 0.428(4) 1 calc R . P A 2
H10A H 0.5231 0.2778 0.5932 0.095 Uiso 0.572(4) 1 calc R . P A 1
H10B H 0.4795 0.2463 0.4964 0.095 Uiso 0.572(4) 1 calc R . P A 1
H10C H 0.5469 0.1974 0.5457 0.095 Uiso 0.572(4) 1 calc R . P A 1
C7 C 0.5292(4) 0.2471(4) 0.0662(6) 0.0598(18) Uani 1 1 d . U . . .
H7BD H 0.5220 0.2748 0.0033 0.090 Uiso 0.428(4) 1 calc R . P A 2
H7BE H 0.5481 0.1955 0.0520 0.090 Uiso 0.428(4) 1 calc R . P A 2
H7BF H 0.4803 0.2437 0.1016 0.090 Uiso 0.428(4) 1 calc R . P A 2
H7AA H 0.5096 0.1985 0.0919 0.090 Uiso 0.572(4) 1 calc R . P A 1
H7AB H 0.5007 0.2894 0.0965 0.090 Uiso 0.572(4) 1 calc R . P A 1
H7AC H 0.5229 0.2486 -0.0066 0.090 Uiso 0.572(4) 1 calc R . P A 1
C8 C 0.6572(4) 0.3203(5) 0.0638(5) 0.0536(16) Uani 1 1 d . U . . .
H8BD H 0.6378 0.3416 0.0010 0.080 Uiso 0.428(4) 1 calc R . P A 2
H8BE H 0.6844 0.3602 0.1011 0.080 Uiso 0.428(4) 1 calc R . P A 2
H8BF H 0.6923 0.2781 0.0492 0.080 Uiso 0.428(4) 1 calc R . P A 2
H8AA H 0.6548 0.3264 -0.0089 0.080 Uiso 0.572(4) 1 calc R . P A 1
H8AB H 0.6357 0.3657 0.0962 0.080 Uiso 0.572(4) 1 calc R . P A 1
H8AC H 0.7106 0.3141 0.0844 0.080 Uiso 0.572(4) 1 calc R . P A 1
C5B C 0.6741(14) 0.1079(12) 0.406(2) 0.057(5) Uani 0.428(4) 1 d D U P A 2
H5BA H 0.6776 0.0630 0.3622 0.086 Uiso 0.428(4) 1 calc GR . P A 2
H5BB H 0.6368 0.0982 0.4589 0.086 Uiso 0.428(4) 1 calc GR . P A 2
H5BC H 0.7242 0.1184 0.4353 0.086 Uiso 0.428(4) 1 calc GR . P A 2
O1B O 0.7244(10) -0.0837(11) 0.2893(19) 0.087(5) Uani 0.487(10) 1 d . U P B 2
O2A O 0.6606(9) -0.1729(9) 0.4010(10) 0.072(4) Uani 0.513(10) 1 d . U P B 1
C11 C 0.6616(4) 0.3072(5) 0.5252(6) 0.066(2) Uani 1 1 d . U . . .
H11D H 0.6761 0.2999 0.5953 0.099 Uiso 0.428(4) 1 calc GR . P A 2
H11E H 0.6366 0.3570 0.5173 0.099 Uiso 0.428(4) 1 calc GR . P A 2
H11F H 0.7074 0.3053 0.4831 0.099 Uiso 0.428(4) 1 calc GR . P A 2
H11A H 0.6506 0.3456 0.5765 0.099 Uiso 0.572(4) 1 calc GR . P A 1
H11B H 0.7004 0.3270 0.4791 0.099 Uiso 0.572(4) 1 calc GR . P A 1
H11C H 0.6805 0.2605 0.5570 0.099 Uiso 0.572(4) 1 calc GR . P A 1
C9B C 0.6180(9) 0.2573(9) 0.5002(11) 0.042(3) Uani 0.428(4) 1 d . U P A 2
H9B H 0.6417 0.2101 0.5288 0.050 Uiso 0.428(4) 1 calc R . P A 2
C6B C 0.5863(8) 0.2889(8) 0.1304(10) 0.035(2) Uani 0.428(4) 1 d . U P A 2
H6B H 0.5584 0.3368 0.1489 0.041 Uiso 0.428(4) 1 calc R . P A 2
S1B S 0.44946(18) 0.3703(2) 0.2616(3) 0.0397(12) Uani 0.428(4) 1 d . . P A 2
C4A C 0.6707(11) 0.1092(10) 0.1889(15) 0.054(4) Uani 0.572(4) 1 d D U P A 1
H4AA H 0.6304 0.0919 0.1433 0.081 Uiso 0.572(4) 1 calc GR . P A 1
H4AB H 0.6855 0.0671 0.2330 0.081 Uiso 0.572(4) 1 calc GR . P A 1
H4AC H 0.7151 0.1259 0.1500 0.081 Uiso 0.572(4) 1 calc GR . P A 1
N2A N 0.6039(7) 0.2553(8) 0.3654(10) 0.031(2) Uani 0.572(4) 1 d . U P A 1
N1A N 0.6160(7) 0.2424(7) 0.2004(9) 0.030(2) Uani 0.572(4) 1 d . U P A 1
C3A C 0.6316(9) 0.1818(11) 0.3445(17) 0.036(3) Uani 0.572(4) 1 d D U P A 1
C1B C 0.5907(11) 0.2898(11) 0.3160(13) 0.024(3) Uani 0.428(4) 1 d . U P A 2
C2A C 0.6413(12) 0.1751(8) 0.2511(15) 0.034(2) Uani 0.572(4) 1 d D U P A 1
C9A C 0.5857(6) 0.2886(6) 0.4649(7) 0.0341(18) Uani 0.572(4) 1 d . U P A 1
H9A H 0.5625 0.3395 0.4500 0.041 Uiso 0.572(4) 1 calc R . P A 1
C6A C 0.6146(6) 0.2547(6) 0.0926(8) 0.0369(18) Uani 0.572(4) 1 d . U P A 1
H6A H 0.6409 0.2097 0.0618 0.044 Uiso 0.572(4) 1 calc R . P A 1
C5A C 0.6532(10) 0.1249(10) 0.4226(14) 0.059(4) Uani 0.572(4) 1 d D U P A 1
H5AA H 0.6616 0.1512 0.4863 0.088 Uiso 0.572(4) 1 calc GR . P A 1
H5AB H 0.7002 0.0987 0.4024 0.088 Uiso 0.572(4) 1 calc GR . P A 1
H5AC H 0.6120 0.0875 0.4302 0.088 Uiso 0.572(4) 1 calc GR . P A 1
C4B C 0.6529(15) 0.1239(13) 0.1618(19) 0.056(5) Uani 0.428(4) 1 d D U P A 2
H4BA H 0.7032 0.1324 0.1315 0.083 Uiso 0.428(4) 1 calc GR . P A 2
H4BB H 0.6139 0.1228 0.1093 0.083 Uiso 0.428(4) 1 calc GR . P A 2
H4BC H 0.6530 0.0750 0.1975 0.083 Uiso 0.428(4) 1 calc GR . P A 2
C12A C 0.5831(10) -0.1173(11) 0.2548(14) 0.067(3) Uani 0.513(10) 1 d . U P B 1
F2A F 0.5885(7) -0.0882(10) 0.1640(9) 0.115(5) Uani 0.513(10) 1 d . U P B 1
F1A F 0.5388(7) -0.1821(7) 0.2524(11) 0.105(4) Uani 0.513(10) 1 d . U P B 1
F3A F 0.5445(6) -0.0704(8) 0.3120(10) 0.104(4) Uani 0.513(10) 1 d . U P B 1
O3B O 0.6580(8) -0.1773(9) 0.1942(9) 0.072(4) Uani 0.487(10) 1 d . U P B 2
F2B F 0.5646(9) -0.0566(10) 0.2409(14) 0.128(5) Uani 0.487(10) 1 d . U P B 2
F3B F 0.5793(8) -0.0798(9) 0.4098(10) 0.124(5) Uani 0.487(10) 1 d . U P B 2
F1B F 0.5307(5) -0.1611(8) 0.3202(9) 0.102(4) Uani 0.487(10) 1 d . U P B 2
C12B C 0.5802(10) -0.1080(12) 0.3137(16) 0.074(3) Uani 0.487(10) 1 d . U P B 2
O3A O 0.6935(11) -0.2023(9) 0.2355(14) 0.109(5) Uani 0.513(10) 1 d . U P B 1
O1A O 0.7072(9) -0.0649(8) 0.3048(16) 0.071(4) Uani 0.513(10) 1 d . U P B 1
O2B O 0.7042(12) -0.1850(10) 0.3680(13) 0.094(5) Uani 0.487(10) 1 d . U P B 2


_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
P1B S1B 2.119(4) 2_655 ?
P1B S1B 2.109(4) . ?
P1B C1B 1.82(2) . ?
S2 O1B 1.345(19) . ?
S2 O2A 1.515(14) . ?
S2 C12A 1.754(19) . ?
S2 O3B 1.533(12) . ?
S2 C12B 1.773(19) . ?
S2 O3A 1.377(14) . ?
S2 O1A 1.470(15) . ?
S2 O2B 1.318(15) . ?
P1A S1A 2.121(3) 2_655 ?
P1A S1A 2.129(3) . ?
P1A C1A 1.843(14) . ?
S1A P1A 2.121(3) 4_565 ?
C3B C2B 1.52(4) . ?
C3B N2B 1.38(3) . ?
C3B C5B 1.501(18) . ?
N1B C2B 1.31(3) . ?
N1B C6B 1.45(2) . ?
N1B C1B 1.36(2) . ?
C2B C4B 1.512(17) . ?
N2B C9B 1.57(2) . ?
N2B C1B 1.34(2) . ?
C1A N2A 1.362(16) . ?
C1A N1A 1.352(16) . ?
C10 H10D 0.9800 . ?
C10 H10E 0.9800 . ?
C10 H10F 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C10 C9B 1.619(17) . ?
C10 C9A 1.497(12) . ?
C7 H7BD 0.9800 . ?
C7 H7BE 0.9800 . ?
C7 H7BF 0.9800 . ?
C7 H7AA 0.9800 . ?
C7 H7AB 0.9800 . ?
C7 H7AC 0.9800 . ?
C7 C6B 1.508(13) . ?
C7 C6A 1.542(12) . ?
C8 H8BD 0.9800 . ?
C8 H8BE 0.9800 . ?
C8 H8BF 0.9800 . ?
C8 H8AA 0.9800 . ?
C8 H8AB 0.9800 . ?
C8 H8AC 0.9800 . ?
C8 C6B 1.624(15) . ?
C8 C6A 1.423(13) . ?
C5B H5BA 0.9800 . ?
C5B H5BB 0.9800 . ?
C5B H5BC 0.9800 . ?
C11 H11D 0.9800 . ?
C11 H11E 0.9800 . ?
C11 H11F 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C11 C9B 1.206(18) . ?
C11 C9A 1.587(12) . ?
C9B H9B 1.0000 . ?
C6B H6B 1.0000 . ?
S1B P1B 2.119(4) 4_565 ?
C4A H4AA 0.9800 . ?
C4A H4AB 0.9800 . ?
C4A H4AC 0.9800 . ?
C4A C2A 1.513(14) . ?
N2A C3A 1.40(2) . ?
N2A C9A 1.488(17) . ?
N1A C2A 1.428(18) . ?
N1A C6A 1.458(16) . ?
C3A C2A 1.27(3) . ?
C3A C5A 1.491(15) . ?
C9A H9A 1.0000 . ?
C6A H6A 1.0000 . ?
C5A H5AA 0.9800 . ?
C5A H5AB 0.9800 . ?
C5A H5AC 0.9800 . ?
C4B H4BA 0.9800 . ?
C4B H4BB 0.9800 . ?
C4B H4BC 0.9800 . ?
C12A F2A 1.32(2) . ?
C12A F1A 1.375(19) . ?
C12A F3A 1.31(2) . ?
F2B C12B 1.35(3) . ?
F3B C12B 1.38(2) . ?
F1B C12B 1.27(2) . ?

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
S1B P1B S1B 109.2(3) . 2_655 ?
C1B P1B S1B 96.6(6) . . ?
C1B P1B S1B 97.6(6) . 2_655 ?
O1B S2 O3B 111.3(12) . . ?
O1B S2 C12B 110.9(10) . . ?
O2A S2 C12A 103.4(8) . . ?
O3B S2 C12B 94.1(9) . . ?
O3A S2 O2A 108.3(10) . . ?
O3A S2 C12A 102.5(11) . . ?
O3A S2 O1A 131.0(11) . . ?
O1A S2 O2A 108.9(10) . . ?
O1A S2 C12A 98.7(8) . . ?
O2B S2 O1B 103.6(13) . . ?
O2B S2 O3B 119.4(10) . . ?
O2B S2 C12B 117.7(11) . . ?
S1A P1A S1A 105.3(3) 2_655 . ?
C1A P1A S1A 97.2(5) . 2_655 ?
C1A P1A S1A 99.0(4) . . ?
P1A S1A P1A 95.52(17) 4_565 . ?
C2B C3B C5B 133(3) . . ?
N2B C3B C2B 101.4(17) . . ?
N2B C3B C5B 125(2) . . ?
C2B N1B C6B 121.7(16) . . ?
C2B N1B C1B 114.0(18) . . ?
C1B N1B C6B 124.3(16) . . ?
C3B C2B C4B 120(2) . . ?
N1B C2B C3B 105.5(19) . . ?
N1B C2B C4B 135(2) . . ?
C3B N2B C9B 121.6(17) . . ?
C1B N2B C3B 113.9(18) . . ?
C1B N2B C9B 124.5(16) . . ?
N2A C1A P1A 128.1(12) . . ?
N1A C1A P1A 121.4(10) . . ?
N1A C1A N2A 110.4(13) . . ?
H10D C10 H10E 109.5 . . ?
H10D C10 H10F 109.5 . . ?
H10E C10 H10F 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C9B C10 H10D 109.5 . . ?
C9B C10 H10E 109.5 . . ?
C9B C10 H10F 109.5 . . ?
C9A C10 H10A 109.5 . . ?
C9A C10 H10B 109.5 . . ?
C9A C10 H10C 109.5 . . ?
H7BD C7 H7BE 109.5 . . ?
H7BD C7 H7BF 109.5 . . ?
H7BE C7 H7BF 109.5 . . ?
H7AA C7 H7AB 109.5 . . ?
H7AA C7 H7AC 109.5 . . ?
H7AB C7 H7AC 109.5 . . ?
C6B C7 H7BD 109.5 . . ?
C6B C7 H7BE 109.5 . . ?
C6B C7 H7BF 109.5 . . ?
C6A C7 H7AA 109.5 . . ?
C6A C7 H7AB 109.5 . . ?
C6A C7 H7AC 109.5 . . ?
H8BD C8 H8BE 109.5 . . ?
H8BD C8 H8BF 109.5 . . ?
H8BE C8 H8BF 109.5 . . ?
H8AA C8 H8AB 109.5 . . ?
H8AA C8 H8AC 109.5 . . ?
H8AB C8 H8AC 109.5 . . ?
C6B C8 H8BD 109.5 . . ?
C6B C8 H8BE 109.5 . . ?
C6B C8 H8BF 109.5 . . ?
C6A C8 H8AA 109.5 . . ?
C6A C8 H8AB 109.5 . . ?
C6A C8 H8AC 109.5 . . ?
C3B C5B H5BA 109.5 . . ?
C3B C5B H5BB 109.5 . . ?
C3B C5B H5BC 109.5 . . ?
H5BA C5B H5BB 109.5 . . ?
H5BA C5B H5BC 109.5 . . ?
H5BB C5B H5BC 109.5 . . ?
H11D C11 H11E 109.5 . . ?
H11D C11 H11F 109.5 . . ?
H11E C11 H11F 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C9B C11 H11D 109.5 . . ?
C9B C11 H11E 109.5 . . ?
C9B C11 H11F 109.5 . . ?
C9A C11 H11A 109.5 . . ?
C9A C11 H11B 109.5 . . ?
C9A C11 H11C 109.5 . . ?
N2B C9B C10 103.8(11) . . ?
N2B C9B H9B 103.3 . . ?
C10 C9B H9B 103.3 . . ?
C11 C9B N2B 113.2(13) . . ?
C11 C9B C10 127.1(13) . . ?
C11 C9B H9B 103.3 . . ?
N1B C6B C7 116.3(12) . . ?
N1B C6B C8 118.0(11) . . ?
N1B C6B H6B 103.0 . . ?
C7 C6B C8 111.0(9) . . ?
C7 C6B H6B 103.0 . . ?
C8 C6B H6B 103.0 . . ?
P1B S1B P1B 96.6(2) . 4_565 ?
H4AA C4A H4AB 109.5 . . ?
H4AA C4A H4AC 109.5 . . ?
H4AB C4A H4AC 109.5 . . ?
C2A C4A H4AA 109.5 . . ?
C2A C4A H4AB 109.5 . . ?
C2A C4A H4AC 109.5 . . ?
C1A N2A C3A 105.8(13) . . ?
C1A N2A C9A 126.4(13) . . ?
C3A N2A C9A 127.7(13) . . ?
C1A N1A C2A 104.0(13) . . ?
C1A N1A C6A 129.4(11) . . ?
C2A N1A C6A 126.6(11) . . ?
N2A C3A C5A 124.1(18) . . ?
C2A C3A N2A 109.1(14) . . ?
C2A C3A C5A 126.5(17) . . ?
N1B C1B P1B 130.7(16) . . ?
N2B C1B P1B 124.0(14) . . ?
N2B C1B N1B 105.2(17) . . ?
N1A C2A C4A 118.2(15) . . ?
C3A C2A C4A 131.2(15) . . ?
C3A C2A N1A 110.5(14) . . ?
C10 C9A C11 110.6(7) . . ?
C10 C9A H9A 105.0 . . ?
C11 C9A H9A 105.0 . . ?
N2A C9A C10 119.2(9) . . ?
N2A C9A C11 110.8(8) . . ?
N2A C9A H9A 105.0 . . ?
C7 C6A H6A 106.5 . . ?
C8 C6A C7 121.1(9) . . ?
C8 C6A N1A 112.2(8) . . ?
C8 C6A H6A 106.5 . . ?
N1A C6A C7 103.3(8) . . ?
N1A C6A H6A 106.5 . . ?
C3A C5A H5AA 109.5 . . ?
C3A C5A H5AB 109.5 . . ?
C3A C5A H5AC 109.5 . . ?
H5AA C5A H5AB 109.5 . . ?
H5AA C5A H5AC 109.5 . . ?
H5AB C5A H5AC 109.5 . . ?
C2B C4B H4BA 109.5 . . ?
C2B C4B H4BB 109.5 . . ?
C2B C4B H4BC 109.5 . . ?
H4BA C4B H4BB 109.5 . . ?
H4BA C4B H4BC 109.5 . . ?
H4BB C4B H4BC 109.5 . . ?
F2A C12A S2 108.9(11) . . ?
F2A C12A F1A 109.7(15) . . ?
F1A C12A S2 108.7(13) . . ?
F3A C12A S2 116.1(14) . . ?
F3A C12A F2A 109.4(19) . . ?
F3A C12A F1A 103.9(14) . . ?
F2B C12B S2 108.7(14) . . ?
F2B C12B F3B 116(2) . . ?
F3B C12B S2 104.5(13) . . ?
F1B C12B S2 113.5(15) . . ?
F1B C12B F2B 113.4(18) . . ?
F1B C12B F3B 100.9(16) . . ?

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
P1A C1A N2A C3A 173.9(11) . . . . ?
P1A C1A N2A C9A -4(2) . . . . ?
P1A C1A N1A C2A -176.3(12) . . . . ?
P1A C1A N1A C6A 3.3(18) . . . . ?
S1A P1A C1A N2A -48.1(12) . . . . ?
S1A P1A C1A N2A 58.7(12) 2_655 . . . ?
S1A P1A C1A N1A -126.2(10) 2_655 . . . ?
S1A P1A C1A N1A 127.0(10) . . . . ?
C3B N2B C9B C10 -109.0(17) . . . . ?
C3B N2B C9B C11 109.7(19) . . . . ?
C3B N2B C1B P1B -177.2(15) . . . . ?
C3B N2B C1B N1B 0(2) . . . . ?
C2B C3B N2B C9B 179.8(18) . . . . ?
C2B C3B N2B C1B 0(2) . . . . ?
C2B N1B C6B C7 64(2) . . . . ?
C2B N1B C6B C8 -72(2) . . . . ?
C2B N1B C1B P1B 177.8(19) . . . . ?
C2B N1B C1B N2B 1(2) . . . . ?
N2B C3B C2B N1B 1(2) . . . . ?
N2B C3B C2B C4B -173(2) . . . . ?
C1A N2A C3A C2A 3.4(19) . . . . ?
C1A N2A C3A C5A 177.6(15) . . . . ?
C1A N2A C9A C10 120.2(14) . . . . ?
C1A N2A C9A C11 -109.8(13) . . . . ?
C1A N1A C2A C4A -179.7(16) . . . . ?
C1A N1A C2A C3A 3(2) . . . . ?
C1A N1A C6A C7 -74.6(14) . . . . ?
C1A N1A C6A C8 57.4(16) . . . . ?
C5B C3B C2B N1B 171(2) . . . . ?
C5B C3B C2B C4B -4(4) . . . . ?
C5B C3B N2B C9B 9(3) . . . . ?
C5B C3B N2B C1B -171(2) . . . . ?
O1B S2 C12B F2B 52(2) . . . . ?
O1B S2 C12B F3B -71.7(18) . . . . ?
O1B S2 C12B F1B 179.3(18) . . . . ?
O2A S2 C12A F2A 179.0(14) . . . . ?
O2A S2 C12A F1A -61.5(15) . . . . ?
O2A S2 C12A F3A 55.1(16) . . . . ?
C9B N2B C1B P1B 3(3) . . . . ?
C9B N2B C1B N1B 179.3(14) . . . . ?
C6B N1B C2B C3B 175.9(17) . . . . ?
C6B N1B C2B C4B -11(4) . . . . ?
C6B N1B C1B P1B 0(3) . . . . ?
C6B N1B C1B N2B -176.1(15) . . . . ?
S1B P1B C1B N1B -57.2(18) 2_655 . . . ?
S1B P1B C1B N1B 53.3(18) . . . . ?
S1B P1B C1B N2B 118.7(16) 2_655 . . . ?
S1B P1B C1B N2B -130.8(17) . . . . ?
N2A C1A N1A C2A -0.5(16) . . . . ?
N2A C1A N1A C6A 179.1(11) . . . . ?
N2A C3A C2A C4A 179.1(19) . . . . ?
N2A C3A C2A N1A -4(2) . . . . ?
N1A C1A N2A C3A -1.6(16) . . . . ?
N1A C1A N2A C9A -179.4(11) . . . . ?
C3A N2A C9A C10 -57.1(17) . . . . ?
C3A N2A C9A C11 72.9(16) . . . . ?
C1B N1B C2B C3B -2(3) . . . . ?
C1B N1B C2B C4B 172(3) . . . . ?
C1B N1B C6B C7 -119.2(16) . . . . ?
C1B N1B C6B C8 105.1(17) . . . . ?
C1B N2B C9B C10 71(2) . . . . ?
C1B N2B C9B C11 -70(2) . . . . ?
C2A N1A C6A C7 104.9(15) . . . . ?
C2A N1A C6A C8 -123.1(16) . . . . ?
C9A N2A C3A C2A -178.9(16) . . . . ?
C9A N2A C3A C5A -5(2) . . . . ?
C6A N1A C2A C4A 1(2) . . . . ?
C6A N1A C2A C3A -176.9(15) . . . . ?
C5A C3A C2A C4A 5(4) . . . . ?
C5A C3A C2A N1A -177.9(16) . . . . ?
O3B S2 C12B F2B -62.5(17) . . . . ?
O3B S2 C12B F3B 173.7(14) . . . . ?
O3B S2 C12B F1B 64.7(17) . . . . ?
O3A S2 C12A F2A -68.4(17) . . . . ?
O3A S2 C12A F1A 51.0(15) . . . . ?
O3A S2 C12A F3A 167.6(15) . . . . ?
O1A S2 C12A F2A 67.1(16) . . . . ?
O1A S2 C12A F1A -173.5(14) . . . . ?
O1A S2 C12A F3A -56.8(17) . . . . ?
O2B S2 C12B F2B 171.1(15) . . . . ?
O2B S2 C12B F3B 47.2(17) . . . . ?
O2B S2 C12B F1B -61.8(19) . . . . ?

# start Validation Reply Form
_vrf_STRVA01_jjw0369             
;
PROBLEM: Flack test results are ambiguous.
RESPONSE: The crystal was refined as an inversion twin. However, the resulting BASF of 0.32(18) could not be precisely determined.
;
_vrf_PLAT089_jjw0369             
;
PROBLEM: Poor Data / Parameter Ratio (Zmax < 18) ........       7.03 Note  
RESPONSE: 378 Parameter were refined with 4006 Data > 4 sigma.
;
_vrf_PLAT869_jjw0369             
;
PROBLEM: ALERTS Related to the use of SQUEEZE Suppressed           ! Info 
RESPONSE: Squeeze was applied to remove electron density of solvent molecules, which could not be determined.
Total Potential Solvent Accessible Void Vol ..................   627.1 Ang^3
Electron Count / Cell =    229
;
# end Validation Reply Form

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'

loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.68(18)
2 0.32(18)

