# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_mx2512
_database_code_depnum_ccdc_archive 'CCDC 950534'
_audit_update_record             
;
2013-07-16 deposited with the CCDC.
2017-06-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C56 H46 N4 O8 S2'
_chemical_formula_sum            'C56 H46 N4 O8 S2'
_chemical_formula_weight         967.09

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'
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

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

_cell_length_a                   11.660(3)
_cell_length_b                   12.790(2)
_cell_length_c                   20.164(5)
_cell_angle_alpha                75.148(11)
_cell_angle_beta                 83.740(12)
_cell_angle_gamma                72.575(13)
_cell_volume                     2771.6(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    8773
_cell_measurement_theta_min      1.72
_cell_measurement_theta_max      27.46

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.159
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1012
_exptl_absorpt_coefficient_mu    0.150
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7413
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'


_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_monochromator  Confocal
_diffrn_measurement_device_type  'MM007-HF CCD(Saturn 724+)'
_diffrn_measurement_method       'ω scans at fixed χ = 45°'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            29909
_diffrn_reflns_av_R_equivalents  0.0563
_diffrn_reflns_av_sigmaI/netI    0.0558
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         1.05
_diffrn_reflns_theta_max         25.00
_reflns_number_total             9737
_reflns_number_gt                7731
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'Olex2 Ver 1.1'
_computing_molecular_graphics    'Olex2 Ver 1.1'
_computing_publication_material  'SHELX97 (Sheldrick, 2008)'


_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. 
;

loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.000 0.500 0.000 450 109 ' '
_platon_squeeze_details          
;
The unit cell contains 2 acetic ether molecules which have been 
treated as a diffuse conteibution to the scattering without specific 
atom positions by SQUEEZE/PLATON.
;

_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)+(0.0870P)²+1.2265P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         9737
_refine_ls_number_parameters     674
_refine_ls_number_restraints     126
_refine_ls_R_factor_all          0.0873
_refine_ls_R_factor_gt           0.0710
_refine_ls_wR_factor_ref         0.1936
_refine_ls_wR_factor_gt          0.1810
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_restrained_S_all      1.089
_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
S1 S 0.08101(7) 0.87866(7) 0.20633(4) 0.0558(2) Uani 1 1 d . . .
S2 S 0.16490(7) 0.96963(6) 0.24732(4) 0.0532(2) Uani 1 1 d . . .
O1 O 0.2779(2) 0.5432(2) 0.33368(12) 0.0930(9) Uani 1 1 d . . .
O2 O 0.2452(3) 0.4347(2) 0.19677(14) 0.0899(8) Uani 1 1 d D . .
O3 O 0.3825(4) 0.3180(3) 0.27109(17) 0.1195(12) Uani 1 1 d . . .
O4 O 0.4542(2) 0.6982(2) 0.37994(14) 0.0801(7) Uani 1 1 d . . .
O5 O 0.3927(2) 0.8694(2) 0.49174(17) 0.0915(9) Uani 1 1 d U . .
O6 O 0.4877(2) 0.6928(2) 0.53990(14) 0.0804(7) Uani 1 1 d U . .
O7 O 0.3005(2) 0.5600(2) 0.59122(14) 0.0806(7) Uani 1 1 d . . .
O29 O 0.6298(3) 0.3988(3) 0.21776(18) 0.1278(13) Uani 1 1 d . . .
N1 N 0.2707(2) 0.7864(2) 0.12708(12) 0.0517(6) Uani 1 1 d . . .
N2 N 0.5287(3) 0.4900(3) 0.29627(17) 0.0915(10) Uani 1 1 d . . .
H2A H 0.5916 0.4743 0.3197 0.110 Uiso 1 1 calc R . .
H2B H 0.4606 0.5290 0.3098 0.110 Uiso 1 1 calc R . .
N3 N 0.06617(19) 0.90900(17) 0.37515(11) 0.0419(5) Uani 1 1 d . . .
N4 N 0.3475(3) 0.5490(3) 0.48178(19) 0.0936(11) Uani 1 1 d . . .
H4A H 0.3754 0.4775 0.4992 0.112 Uiso 1 1 d R . .
H4B H 0.2867 0.5605 0.4573 0.112 Uiso 1 1 d R . .
C1 C 0.2002(3) 0.7713(2) 0.18605(14) 0.0498(7) Uani 1 1 d . . .
C2 C 0.2468(3) 0.6607(3) 0.22409(15) 0.0530(7) Uani 1 1 d . . .
C3 C 0.3487(3) 0.6090(2) 0.18592(15) 0.0531(7) Uani 1 1 d . A .
C4 C 0.3612(3) 0.6881(3) 0.12659(15) 0.0543(7) Uani 1 1 d . . .
C5 C 0.2034(3) 0.6068(3) 0.29200(16) 0.0608(8) Uani 1 1 d . . .
C6 C 0.0741(3) 0.6226(3) 0.31041(17) 0.0614(8) Uani 1 1 d . . .
C7 C -0.0106(4) 0.6460(4) 0.2620(2) 0.0839(11) Uani 1 1 d . . .
H7 H 0.0118 0.6595 0.2156 0.101 Uiso 1 1 calc R . .
C8 C -0.1285(5) 0.6493(4) 0.2820(3) 0.1095(15) Uani 1 1 d . . .
H8 H -0.1849 0.6640 0.2491 0.131 Uiso 1 1 calc R . .
C9 C -0.1619(5) 0.6312(4) 0.3495(3) 0.1110(17) Uani 1 1 d . . .
H9 H -0.2413 0.6332 0.3628 0.133 Uiso 1 1 calc R . .
C10 C -0.0797(5) 0.6099(4) 0.3985(3) 0.1030(16) Uani 1 1 d . . .
H10 H -0.1040 0.5994 0.4446 0.124 Uiso 1 1 calc R . .
C11 C 0.0387(4) 0.6042(3) 0.37950(19) 0.0770(11) Uani 1 1 d . . .
H11 H 0.0947 0.5880 0.4128 0.092 Uiso 1 1 calc R . .
C12 C 0.4219(3) 0.4864(3) 0.19961(17) 0.0646(9) Uani 1 1 d . . .
H12 H 0.4510 0.4738 0.1540 0.078 Uiso 1 1 calc R A .
C13 C 0.5367(4) 0.4543(3) 0.2400(2) 0.0788(11) Uani 1 1 d . A .
C14 C 0.3490(4) 0.4040(3) 0.22750(19) 0.0805(11) Uani 1 1 d . A .
C15 C 0.1524(7) 0.3763(6) 0.2223(4) 0.095(2) Uani 0.747(10) 1 d PDU A 1
H15A H 0.0733 0.4284 0.2120 0.114 Uiso 0.747(10) 1 calc PR A 1
H15B H 0.1565 0.3482 0.2717 0.114 Uiso 0.747(10) 1 calc PR A 1
C16 C 0.1721(7) 0.2813(6) 0.1892(5) 0.127(3) Uani 0.747(10) 1 d PDU A 1
H16A H 0.1622 0.3101 0.1407 0.190 Uiso 0.747(10) 1 calc PR A 1
H16B H 0.1148 0.2400 0.2079 0.190 Uiso 0.747(10) 1 calc PR A 1
H16C H 0.2521 0.2322 0.1975 0.190 Uiso 0.747(10) 1 calc PR A 1
C17 C 0.4472(3) 0.6755(3) 0.06821(17) 0.0644(9) Uani 1 1 d . . .
C18 C 0.5695(4) 0.6413(4) 0.0791(3) 0.0953(13) Uani 1 1 d . . .
H18 H 0.5976 0.6296 0.1226 0.114 Uiso 1 1 calc R . .
C19 C 0.6507(5) 0.6244(5) 0.0229(4) 0.133(2) Uani 1 1 d . . .
H19 H 0.7332 0.6018 0.0290 0.160 Uiso 1 1 calc R . .
C20 C 0.6069(7) 0.6416(6) -0.0408(4) 0.142(3) Uani 1 1 d . . .
H20 H 0.6609 0.6291 -0.0774 0.171 Uiso 1 1 calc R . .
C21 C 0.4887(7) 0.6760(5) -0.0515(3) 0.127(2) Uani 1 1 d . . .
H21 H 0.4611 0.6882 -0.0952 0.152 Uiso 1 1 calc R . .
C22 C 0.4079(5) 0.6931(4) 0.00281(19) 0.0961(14) Uani 1 1 d . . .
H22 H 0.3258 0.7168 -0.0047 0.115 Uiso 1 1 calc R . .
C23 C 0.2627(3) 0.8932(3) 0.07866(15) 0.0573(8) Uani 1 1 d . . .
C24 C 0.1796(4) 0.9317(3) 0.0284(2) 0.0882(12) Uani 1 1 d . . .
H24 H 0.1281 0.8901 0.0254 0.106 Uiso 1 1 calc R . .
C25 C 0.1742(6) 1.0348(5) -0.0180(3) 0.1189(18) Uani 1 1 d . . .
H25 H 0.1190 1.0620 -0.0527 0.143 Uiso 1 1 calc R . .
C26 C 0.2502(6) 1.0968(4) -0.0128(3) 0.120(2) Uani 1 1 d . . .
H26 H 0.2464 1.1653 -0.0439 0.144 Uiso 1 1 calc R . .
C27 C 0.3308(6) 1.0570(5) 0.0382(3) 0.1260(19) Uani 1 1 d . . .
H27 H 0.3812 1.0989 0.0425 0.151 Uiso 1 1 calc R . .
C28 C 0.3375(4) 0.9543(4) 0.0835(2) 0.0938(13) Uani 1 1 d . . .
H28 H 0.3937 0.9266 0.1177 0.113 Uiso 1 1 calc R . .
C29 C 0.1696(2) 0.9020(2) 0.33451(13) 0.0442(6) Uani 1 1 d . . .
C30 C 0.2659(2) 0.8308(2) 0.37440(14) 0.0447(6) Uani 1 1 d . . .
C31 C 0.2178(2) 0.7942(2) 0.44155(14) 0.0438(6) Uani 1 1 d . B .
C32 C 0.0941(2) 0.8419(2) 0.44055(13) 0.0405(6) Uani 1 1 d . . .
C33 C 0.3925(3) 0.7920(3) 0.35137(16) 0.0546(7) Uani 1 1 d . . .
C34 C 0.4479(3) 0.8639(3) 0.29436(16) 0.0593(8) Uani 1 1 d . . .
C35 C 0.5339(3) 0.8106(4) 0.25138(19) 0.0769(10) Uani 1 1 d . . .
H35 H 0.5539 0.7328 0.2576 0.092 Uiso 1 1 calc R . .
C36 C 0.5893(4) 0.8731(5) 0.1996(2) 0.0974(14) Uani 1 1 d . . .
H36 H 0.6456 0.8372 0.1703 0.117 Uiso 1 1 calc R . .
C37 C 0.5632(4) 0.9874(5) 0.1903(2) 0.0996(14) Uani 1 1 d . . .
H37 H 0.6017 1.0286 0.1550 0.120 Uiso 1 1 calc R . .
C38 C 0.4808(4) 1.0409(4) 0.2329(2) 0.0867(12) Uani 1 1 d . . .
H38 H 0.4635 1.1185 0.2268 0.104 Uiso 1 1 calc R . .
C39 C 0.4228(3) 0.9798(3) 0.28516(18) 0.0646(8) Uani 1 1 d . . .
H39 H 0.3668 1.0165 0.3142 0.077 Uiso 1 1 calc R . .
C40 C 0.2848(3) 0.7329(2) 0.50759(15) 0.0501(7) Uani 1 1 d . . .
H40 H 0.2301 0.7607 0.5437 0.060 Uiso 1 1 calc R B .
C41 C 0.3122(3) 0.6047(3) 0.53072(19) 0.0601(8) Uani 1 1 d . B .
C42 C 0.3971(3) 0.7676(3) 0.51178(17) 0.0639(8) Uani 1 1 d . B .
C43 C 0.5868(6) 0.7349(6) 0.5512(3) 0.084(2) Uani 0.583(6) 1 d PDU B 1
H43A H 0.6373 0.6812 0.5871 0.101 Uiso 0.583(6) 1 calc PR B 1
H43B H 0.5552 0.8061 0.5646 0.101 Uiso 0.583(6) 1 calc PR B 1
C44 C 0.6588(7) 0.7506(9) 0.4835(5) 0.119(3) Uani 0.583(6) 1 d PDU B 1
H44A H 0.6094 0.8080 0.4492 0.179 Uiso 0.583(6) 1 calc PR B 1
H44B H 0.6844 0.6809 0.4691 0.179 Uiso 0.583(6) 1 calc PR B 1
H44C H 0.7280 0.7728 0.4894 0.179 Uiso 0.583(6) 1 calc PR B 1
C45 C 0.0015(2) 0.8287(2) 0.49553(13) 0.0432(6) Uani 1 1 d . . .
C46 C -0.0938(2) 0.9175(2) 0.50801(14) 0.0453(6) Uani 1 1 d . . .
H46 H -0.1007 0.9896 0.4808 0.054 Uiso 1 1 calc R . .
C47 C -0.1788(3) 0.9014(3) 0.55994(16) 0.0566(7) Uani 1 1 d . . .
H47 H -0.2413 0.9624 0.5680 0.068 Uiso 1 1 calc R . .
C48 C -0.1706(3) 0.7943(3) 0.59987(18) 0.0720(10) Uani 1 1 d . . .
H48 H -0.2288 0.7826 0.6341 0.086 Uiso 1 1 calc R . .
C49 C -0.0762(3) 0.7051(3) 0.58896(19) 0.0755(10) Uani 1 1 d . . .
H49 H -0.0697 0.6333 0.6166 0.091 Uiso 1 1 calc R . .
C50 C 0.0089(3) 0.7212(2) 0.53731(16) 0.0554(7) Uani 1 1 d . . .
H50 H 0.0720 0.6600 0.5302 0.066 Uiso 1 1 calc R . .
C51 C -0.0531(2) 0.9765(2) 0.35289(14) 0.0468(6) Uani 1 1 d . . .
C52 C -0.1362(3) 0.9256(3) 0.34485(17) 0.0635(8) Uani 1 1 d . . .
H52 H -0.1157 0.8478 0.3510 0.076 Uiso 1 1 calc R . .
C53 C -0.2519(3) 0.9918(4) 0.3273(2) 0.0933(13) Uani 1 1 d . . .
H53 H -0.3097 0.9580 0.3222 0.112 Uiso 1 1 calc R . .
C54 C -0.2816(4) 1.1065(4) 0.3176(2) 0.0977(14) Uani 1 1 d . . .
H54 H -0.3592 1.1502 0.3058 0.117 Uiso 1 1 calc R . .
C55 C -0.1970(4) 1.1568(3) 0.32516(18) 0.0782(11) Uani 1 1 d . . .
H55 H -0.2176 1.2348 0.3183 0.094 Uiso 1 1 calc R . .
C56 C -0.0807(3) 1.0927(2) 0.34297(15) 0.0573(8) Uani 1 1 d . . .
H56 H -0.0230 1.1266 0.3481 0.069 Uiso 1 1 calc R . .
C44A C 0.5789(13) 0.8994(15) 0.4510(7) 0.145(6) Uani 0.417(6) 1 d PDU B 2
H44D H 0.5389 0.9537 0.4121 0.218 Uiso 0.417(6) 1 calc PR B 2
H44E H 0.6041 0.8259 0.4415 0.218 Uiso 0.417(6) 1 calc PR B 2
H44F H 0.6479 0.9192 0.4600 0.218 Uiso 0.417(6) 1 calc PR B 2
C43A C 0.4940(9) 0.8987(9) 0.5126(6) 0.098(3) Uani 0.417(6) 1 d PDU B 2
H43C H 0.5318 0.8430 0.5524 0.117 Uiso 0.417(6) 1 calc PR B 2
H43D H 0.4675 0.9722 0.5233 0.117 Uiso 0.417(6) 1 calc PR B 2
C15A C 0.217(2) 0.3282(13) 0.2195(16) 0.132(7) Uani 0.253(10) 1 d PDU A 2
H15C H 0.2363 0.2946 0.2673 0.158 Uiso 0.253(10) 1 calc PR A 2
H15D H 0.2620 0.2761 0.1921 0.158 Uiso 0.253(10) 1 calc PR A 2
C16A C 0.082(2) 0.354(3) 0.2107(17) 0.155(9) Uani 0.253(10) 1 d PDU A 2
H16D H 0.0639 0.3845 0.1630 0.232 Uiso 0.253(10) 1 calc PR A 2
H16E H 0.0381 0.4076 0.2366 0.232 Uiso 0.253(10) 1 calc PR A 2
H16F H 0.0580 0.2857 0.2268 0.232 Uiso 0.253(10) 1 calc PR A 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
S1 C1 1.734(3) . ?
S1 S2 2.0843(12) . ?
S2 C29 1.748(3) . ?
O1 C5 1.229(4) . ?
O2 C14 1.325(5) . ?
O2 C15A 1.447(10) . ?
O2 C15 1.469(6) . ?
O3 C14 1.208(4) . ?
O4 C33 1.228(4) . ?
O5 C42 1.247(4) . ?
O5 C43A 1.473(10) . ?
O6 C42 1.265(4) . ?
O6 C43 1.472(7) . ?
O7 C41 1.219(4) . ?
O29 C13 1.217(4) . ?
N1 C1 1.375(4) . ?
N1 C4 1.380(4) . ?
N1 C23 1.445(4) . ?
N2 C13 1.311(5) . ?
N3 C29 1.375(3) . ?
N3 C32 1.388(3) . ?
N3 C51 1.449(3) . ?
N4 C41 1.322(5) . ?
C1 C2 1.399(4) . ?
C2 C3 1.426(4) . ?
C2 C5 1.477(4) . ?
C3 C4 1.380(4) . ?
C3 C12 1.513(4) . ?
C4 C17 1.470(4) . ?
C5 C6 1.478(5) . ?
C6 C7 1.379(5) . ?
C6 C11 1.390(5) . ?
C7 C8 1.381(6) . ?
C8 C9 1.356(7) . ?
C9 C10 1.370(7) . ?
C10 C11 1.377(6) . ?
C12 C14 1.510(6) . ?
C12 C13 1.536(5) . ?
C15 C16 1.480(7) . ?
C17 C22 1.385(5) . ?
C17 C18 1.385(5) . ?
C18 C19 1.413(7) . ?
C19 C20 1.374(9) . ?
C20 C21 1.340(9) . ?
C21 C22 1.382(6) . ?
C23 C28 1.358(5) . ?
C23 C24 1.370(5) . ?
C24 C25 1.397(6) . ?
C25 C26 1.381(8) . ?
C26 C27 1.362(8) . ?
C27 C28 1.380(6) . ?
C29 C30 1.396(4) . ?
C30 C31 1.426(4) . ?
C30 C33 1.474(4) . ?
C31 C32 1.388(4) . ?
C31 C40 1.524(4) . ?
C32 C45 1.475(4) . ?
C33 C34 1.495(4) . ?
C34 C35 1.387(5) . ?
C34 C39 1.389(5) . ?
C35 C36 1.371(6) . ?
C36 C37 1.368(7) . ?
C37 C38 1.362(6) . ?
C38 C39 1.385(5) . ?
C40 C42 1.521(4) . ?
C40 C41 1.528(4) . ?
C43 C44 1.523(8) . ?
C45 C46 1.385(4) . ?
C45 C50 1.399(4) . ?
C46 C47 1.381(4) . ?
C47 C48 1.381(4) . ?
C48 C49 1.372(5) . ?
C49 C50 1.378(4) . ?
C51 C52 1.362(4) . ?
C51 C56 1.388(4) . ?
C52 C53 1.389(5) . ?
C53 C54 1.368(6) . ?
C54 C55 1.369(6) . ?
C55 C56 1.389(5) . ?
C44A C43A 1.501(9) . ?
C15A C16A 1.531(10) . ?

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 S2 103.21(11) . . ?
C29 S2 S1 102.68(10) . . ?
C14 O2 C15A 97.9(10) . . ?
C14 O2 C15 121.4(4) . . ?
C15A O2 C15 32.7(9) . . ?
C42 O5 C43A 114.4(5) . . ?
C42 O6 C43 115.2(4) . . ?
C1 N1 C4 109.4(2) . . ?
C1 N1 C23 125.0(2) . . ?
C4 N1 C23 124.9(2) . . ?
C29 N3 C32 109.4(2) . . ?
C29 N3 C51 125.0(2) . . ?
C32 N3 C51 125.6(2) . . ?
N1 C1 C2 107.8(2) . . ?
N1 C1 S1 122.6(2) . . ?
C2 C1 S1 129.4(2) . . ?
C1 C2 C3 107.0(3) . . ?
C1 C2 C5 127.6(3) . . ?
C3 C2 C5 125.4(3) . . ?
C4 C3 C2 107.5(3) . . ?
C4 C3 C12 123.6(3) . . ?
C2 C3 C12 128.4(3) . . ?
N1 C4 C3 108.3(3) . . ?
N1 C4 C17 122.4(3) . . ?
C3 C4 C17 129.2(3) . . ?
O1 C5 C2 118.5(3) . . ?
O1 C5 C6 119.0(3) . . ?
C2 C5 C6 122.5(3) . . ?
C7 C6 C11 119.1(4) . . ?
C7 C6 C5 122.3(3) . . ?
C11 C6 C5 118.4(3) . . ?
C6 C7 C8 120.4(4) . . ?
C9 C8 C7 120.0(5) . . ?
C8 C9 C10 120.6(5) . . ?
C9 C10 C11 120.2(5) . . ?
C10 C11 C6 119.8(4) . . ?
C14 C12 C3 114.2(3) . . ?
C14 C12 C13 111.2(3) . . ?
C3 C12 C13 116.5(3) . . ?
O29 C13 N2 123.7(4) . . ?
O29 C13 C12 118.5(4) . . ?
N2 C13 C12 117.8(3) . . ?
O3 C14 O2 123.5(4) . . ?
O3 C14 C12 124.2(4) . . ?
O2 C14 C12 112.2(3) . . ?
O2 C15 C16 109.2(5) . . ?
C22 C17 C18 119.4(4) . . ?
C22 C17 C4 121.0(3) . . ?
C18 C17 C4 119.6(3) . . ?
C17 C18 C19 118.7(5) . . ?
C20 C19 C18 119.5(6) . . ?
C21 C20 C19 121.8(5) . . ?
C20 C21 C22 119.5(6) . . ?
C21 C22 C17 121.1(5) . . ?
C28 C23 C24 120.8(3) . . ?
C28 C23 N1 119.6(3) . . ?
C24 C23 N1 119.5(3) . . ?
C23 C24 C25 118.4(5) . . ?
C26 C25 C24 120.5(5) . . ?
C27 C26 C25 119.6(5) . . ?
C26 C27 C28 119.9(5) . . ?
C23 C28 C27 120.6(5) . . ?
N3 C29 C30 108.1(2) . . ?
N3 C29 S2 121.18(19) . . ?
C30 C29 S2 130.6(2) . . ?
C29 C30 C31 107.1(2) . . ?
C29 C30 C33 127.3(3) . . ?
C31 C30 C33 125.4(2) . . ?
C32 C31 C30 107.6(2) . . ?
C32 C31 C40 122.9(2) . . ?
C30 C31 C40 128.6(2) . . ?
C31 C32 N3 107.8(2) . . ?
C31 C32 C45 129.8(2) . . ?
N3 C32 C45 122.5(2) . . ?
O4 C33 C30 119.1(3) . . ?
O4 C33 C34 119.2(3) . . ?
C30 C33 C34 121.8(3) . . ?
C35 C34 C39 118.8(3) . . ?
C35 C34 C33 117.9(3) . . ?
C39 C34 C33 123.2(3) . . ?
C36 C35 C34 119.8(4) . . ?
C37 C36 C35 121.1(4) . . ?
C38 C37 C36 119.9(4) . . ?
C37 C38 C39 120.1(4) . . ?
C38 C39 C34 120.3(3) . . ?
C42 C40 C31 113.3(2) . . ?
C42 C40 C41 109.7(2) . . ?
C31 C40 C41 119.1(2) . . ?
O7 C41 N4 124.1(3) . . ?
O7 C41 C40 119.9(3) . . ?
N4 C41 C40 116.0(3) . . ?
O5 C42 O6 123.2(3) . . ?
O5 C42 C40 118.5(3) . . ?
O6 C42 C40 118.1(3) . . ?
O6 C43 C44 106.7(5) . . ?
C46 C45 C50 117.7(3) . . ?
C46 C45 C32 123.3(2) . . ?
C50 C45 C32 118.9(2) . . ?
C47 C46 C45 121.5(3) . . ?
C46 C47 C48 119.7(3) . . ?
C49 C48 C47 119.9(3) . . ?
C48 C49 C50 120.5(3) . . ?
C49 C50 C45 120.7(3) . . ?
C52 C51 C56 121.7(3) . . ?
C52 C51 N3 120.1(3) . . ?
C56 C51 N3 118.2(3) . . ?
C51 C52 C53 119.0(3) . . ?
C54 C53 C52 120.5(4) . . ?
C53 C54 C55 120.0(3) . . ?
C54 C55 C56 120.7(4) . . ?
C51 C56 C55 118.1(3) . . ?
O5 C43A C44A 103.9(9) . . ?
O2 C15A C16A 106.6(19) . . ?

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
C1 S1 S2 C29 -89.02(14) . . . . ?
C4 N1 C1 C2 0.0(3) . . . . ?
C23 N1 C1 C2 -171.1(3) . . . . ?
C4 N1 C1 S1 177.2(2) . . . . ?
C23 N1 C1 S1 6.1(4) . . . . ?
S2 S1 C1 N1 -80.8(2) . . . . ?
S2 S1 C1 C2 95.8(3) . . . . ?
N1 C1 C2 C3 0.0(3) . . . . ?
S1 C1 C2 C3 -177.0(2) . . . . ?
N1 C1 C2 C5 178.0(3) . . . . ?
S1 C1 C2 C5 1.1(5) . . . . ?
C1 C2 C3 C4 0.0(3) . . . . ?
C5 C2 C3 C4 -178.1(3) . . . . ?
C1 C2 C3 C12 -171.7(3) . . . . ?
C5 C2 C3 C12 10.2(5) . . . . ?
C1 N1 C4 C3 0.0(3) . . . . ?
C23 N1 C4 C3 171.1(3) . . . . ?
C1 N1 C4 C17 176.3(3) . . . . ?
C23 N1 C4 C17 -12.5(5) . . . . ?
C2 C3 C4 N1 0.0(3) . . . . ?
C12 C3 C4 N1 172.2(3) . . . . ?
C2 C3 C4 C17 -176.0(3) . . . . ?
C12 C3 C4 C17 -3.9(6) . . . . ?
C1 C2 C5 O1 -140.6(4) . . . . ?
C3 C2 C5 O1 37.1(5) . . . . ?
C1 C2 C5 C6 42.2(5) . . . . ?
C3 C2 C5 C6 -140.1(3) . . . . ?
O1 C5 C6 C7 -149.5(4) . . . . ?
C2 C5 C6 C7 27.6(5) . . . . ?
O1 C5 C6 C11 25.2(5) . . . . ?
C2 C5 C6 C11 -157.7(3) . . . . ?
C11 C6 C7 C8 -1.0(6) . . . . ?
C5 C6 C7 C8 173.7(4) . . . . ?
C6 C7 C8 C9 1.0(7) . . . . ?
C7 C8 C9 C10 0.3(8) . . . . ?
C8 C9 C10 C11 -1.5(8) . . . . ?
C9 C10 C11 C6 1.5(6) . . . . ?
C7 C6 C11 C10 -0.3(5) . . . . ?
C5 C6 C11 C10 -175.2(3) . . . . ?
C4 C3 C12 C14 -134.2(3) . . . . ?
C2 C3 C12 C14 36.2(5) . . . . ?
C4 C3 C12 C13 93.9(4) . . . . ?
C2 C3 C12 C13 -95.7(4) . . . . ?
C14 C12 C13 O29 95.6(5) . . . . ?
C3 C12 C13 O29 -131.2(4) . . . . ?
C14 C12 C13 N2 -85.4(4) . . . . ?
C3 C12 C13 N2 47.8(5) . . . . ?
C15A O2 C14 O3 -13.0(14) . . . . ?
C15 O2 C14 O3 11.4(6) . . . . ?
C15A O2 C14 C12 164.6(14) . . . . ?
C15 O2 C14 C12 -171.0(4) . . . . ?
C3 C12 C14 O3 -141.5(4) . . . . ?
C13 C12 C14 O3 -7.1(5) . . . . ?
C3 C12 C14 O2 40.9(4) . . . . ?
C13 C12 C14 O2 175.3(3) . . . . ?
C14 O2 C15 C16 -89.6(7) . . . . ?
C15A O2 C15 C16 -40(2) . . . . ?
N1 C4 C17 C22 -56.6(5) . . . . ?
C3 C4 C17 C22 119.0(4) . . . . ?
N1 C4 C17 C18 126.1(4) . . . . ?
C3 C4 C17 C18 -58.4(5) . . . . ?
C22 C17 C18 C19 -0.5(6) . . . . ?
C4 C17 C18 C19 176.9(4) . . . . ?
C17 C18 C19 C20 -0.4(8) . . . . ?
C18 C19 C20 C21 1.1(10) . . . . ?
C19 C20 C21 C22 -1.0(10) . . . . ?
C20 C21 C22 C17 0.1(9) . . . . ?
C18 C17 C22 C21 0.6(7) . . . . ?
C4 C17 C22 C21 -176.8(4) . . . . ?
C1 N1 C23 C28 95.5(4) . . . . ?
C4 N1 C23 C28 -74.3(4) . . . . ?
C1 N1 C23 C24 -84.5(4) . . . . ?
C4 N1 C23 C24 105.8(4) . . . . ?
C28 C23 C24 C25 0.4(6) . . . . ?
N1 C23 C24 C25 -179.6(4) . . . . ?
C23 C24 C25 C26 -0.6(8) . . . . ?
C24 C25 C26 C27 -0.2(9) . . . . ?
C25 C26 C27 C28 1.1(9) . . . . ?
C24 C23 C28 C27 0.5(7) . . . . ?
N1 C23 C28 C27 -179.5(4) . . . . ?
C26 C27 C28 C23 -1.3(9) . . . . ?
C32 N3 C29 C30 -0.9(3) . . . . ?
C51 N3 C29 C30 178.9(2) . . . . ?
C32 N3 C29 S2 175.94(18) . . . . ?
C51 N3 C29 S2 -4.3(4) . . . . ?
S1 S2 C29 N3 -68.5(2) . . . . ?
S1 S2 C29 C30 107.5(3) . . . . ?
N3 C29 C30 C31 -0.2(3) . . . . ?
S2 C29 C30 C31 -176.5(2) . . . . ?
N3 C29 C30 C33 175.2(3) . . . . ?
S2 C29 C30 C33 -1.2(5) . . . . ?
C29 C30 C31 C32 1.1(3) . . . . ?
C33 C30 C31 C32 -174.4(3) . . . . ?
C29 C30 C31 C40 -168.2(3) . . . . ?
C33 C30 C31 C40 16.4(4) . . . . ?
C30 C31 C32 N3 -1.6(3) . . . . ?
C40 C31 C32 N3 168.4(2) . . . . ?
C30 C31 C32 C45 177.9(3) . . . . ?
C40 C31 C32 C45 -12.1(4) . . . . ?
C29 N3 C32 C31 1.5(3) . . . . ?
C51 N3 C32 C31 -178.2(2) . . . . ?
C29 N3 C32 C45 -178.0(2) . . . . ?
C51 N3 C32 C45 2.3(4) . . . . ?
C29 C30 C33 O4 -148.2(3) . . . . ?
C31 C30 C33 O4 26.4(5) . . . . ?
C29 C30 C33 C34 32.1(5) . . . . ?
C31 C30 C33 C34 -153.4(3) . . . . ?
O4 C33 C34 C35 34.6(5) . . . . ?
C30 C33 C34 C35 -145.6(3) . . . . ?
O4 C33 C34 C39 -141.3(3) . . . . ?
C30 C33 C34 C39 38.4(5) . . . . ?
C39 C34 C35 C36 -2.1(5) . . . . ?
C33 C34 C35 C36 -178.2(4) . . . . ?
C34 C35 C36 C37 1.4(7) . . . . ?
C35 C36 C37 C38 -0.1(7) . . . . ?
C36 C37 C38 C39 -0.5(7) . . . . ?
C37 C38 C39 C34 -0.2(6) . . . . ?
C35 C34 C39 C38 1.5(5) . . . . ?
C33 C34 C39 C38 177.4(3) . . . . ?
C32 C31 C40 C42 -133.7(3) . . . . ?
C30 C31 C40 C42 34.1(4) . . . . ?
C32 C31 C40 C41 95.1(3) . . . . ?
C30 C31 C40 C41 -97.1(4) . . . . ?
C42 C40 C41 O7 88.5(4) . . . . ?
C31 C40 C41 O7 -138.8(3) . . . . ?
C42 C40 C41 N4 -91.8(3) . . . . ?
C31 C40 C41 N4 40.9(4) . . . . ?
C43A O5 C42 O6 -8.8(7) . . . . ?
C43A O5 C42 C40 166.1(6) . . . . ?
C43 O6 C42 O5 3.3(6) . . . . ?
C43 O6 C42 C40 -171.6(4) . . . . ?
C31 C40 C42 O5 41.1(4) . . . . ?
C41 C40 C42 O5 176.7(3) . . . . ?
C31 C40 C42 O6 -143.8(3) . . . . ?
C41 C40 C42 O6 -8.1(4) . . . . ?
C42 O6 C43 C44 -82.0(7) . . . . ?
C31 C32 C45 C46 138.1(3) . . . . ?
N3 C32 C45 C46 -42.5(4) . . . . ?
C31 C32 C45 C50 -42.3(4) . . . . ?
N3 C32 C45 C50 137.1(3) . . . . ?
C50 C45 C46 C47 0.2(4) . . . . ?
C32 C45 C46 C47 179.8(3) . . . . ?
C45 C46 C47 C48 -1.2(5) . . . . ?
C46 C47 C48 C49 1.8(6) . . . . ?
C47 C48 C49 C50 -1.6(6) . . . . ?
C48 C49 C50 C45 0.6(6) . . . . ?
C46 C45 C50 C49 0.0(5) . . . . ?
C32 C45 C50 C49 -179.6(3) . . . . ?
C29 N3 C51 C52 109.5(3) . . . . ?
C32 N3 C51 C52 -70.9(4) . . . . ?
C29 N3 C51 C56 -73.1(3) . . . . ?
C32 N3 C51 C56 106.5(3) . . . . ?
C56 C51 C52 C53 -1.0(5) . . . . ?
N3 C51 C52 C53 176.3(3) . . . . ?
C51 C52 C53 C54 0.7(6) . . . . ?
C52 C53 C54 C55 -0.1(7) . . . . ?
C53 C54 C55 C56 -0.2(6) . . . . ?
C52 C51 C56 C55 0.7(4) . . . . ?
N3 C51 C56 C55 -176.7(3) . . . . ?
C54 C55 C56 C51 -0.1(5) . . . . ?
C42 O5 C43A C44A 97.3(10) . . . . ?
C14 O2 C15A C16A 161(2) . . . . ?
C15 O2 C15A C16A 21.8(15) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.268
_refine_diff_density_min         -0.314
_refine_diff_density_rms         0.056
####################################################################### 
# 
# 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_sa4373a
_audit_block_doi                 10.5517/cc1k0kgl
_database_code_depnum_ccdc_archive 'CCDC 1430509'
_audit_update_record             
;
2015-10-09 deposited with the CCDC.
2017-06-16 downloaded from the CCDC.
;
_audit_creation_date             2015-10-09
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C28 H19 F N2 O4 S'
_chemical_formula_sum            'C28 H19 F N2 O4 S'
_chemical_formula_weight         498.51
_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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   18.382(5)
_cell_length_b                   12.608(3)
_cell_length_c                   10.333(3)
_cell_angle_alpha                90
_cell_angle_beta                 97.036(3)
_cell_angle_gamma                90
_cell_volume                     2376.8(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6720
_cell_measurement_temperature    173.1500
_cell_measurement_theta_max      27.4800
_cell_measurement_theta_min      2.1557
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.183
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7754
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.393
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Plate
_exptl_crystal_F_000             1032
_exptl_crystal_size_max          0.52
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.11
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0306
_diffrn_reflns_av_unetI/netI     0.0315
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            16112
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.492
_diffrn_reflns_theta_min         2.756
_diffrn_ambient_temperature      173.1500
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_details      
;
scan:
	Number of images: 360
	           Slice: -110.0000 - 70.0000
	     Image width: 0.5000
	        Exp time: 10.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 270.0000
	             XTD: 45.1096
	          2theta: -19.8130
scan:
	Number of images: 282
	           Slice: -80.0000 - 61.0000
	     Image width: 0.5000
	        Exp time: 10.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 180.0000
	             XTD: 45.1096
	          2theta: -19.8130
;
_diffrn_measurement_device       
;
Saturn724+ (2x2 bin mode)
;
_diffrn_measurement_device_details 
;
AFC10: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  'Saturn724+ CCD'
_diffrn_measurement_method       'ω scans at fixed χ = 45°'
_diffrn_number_total             5669
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      0.0231
_diffrn_orient_matrix_UB_12      0.0824
_diffrn_orient_matrix_UB_13      -0.0468
_diffrn_orient_matrix_UB_21      0.0211
_diffrn_orient_matrix_UB_22      0.0332
_diffrn_orient_matrix_UB_23      0.0689
_diffrn_orient_matrix_UB_31      0.0524
_diffrn_orient_matrix_UB_32      -0.0125
_diffrn_orient_matrix_UB_33      -0.0101
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Sealed Tube'
_diffrn_source_current           30.0000
_diffrn_source_power             1.5000
_diffrn_source_voltage           50.0000
_diffrn_special_details          
;
 ?
;
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4964
_reflns_number_total             5404
_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       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'CIFTAB (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2014)'
_computing_structure_solution    
;
'SHELXT (Sheldrick, 2014)'
;
_refine_diff_density_max         0.433
_refine_diff_density_min         -0.250
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.168
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     326
_refine_ls_number_reflns         5404
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0555
_refine_ls_R_factor_gt           0.0485
_refine_ls_restrained_S_all      1.168
_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)+(0.0200P)²+1.3176P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0899
_refine_ls_wR_factor_ref         0.0939
_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.a Secondary CH2 refined with riding coordinates:
 C27(H27A,H27B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C13(H13), C14(H14), C15(H15), C16(H16),
 C17(H17), C20(H20), C21(H21), C22(H22), C23(H23), C24(H24)
2.c Idealised Me refined as rotating group:
 C28(H28A,H28B,H28C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.04349(2) 0.85376(4) 0.07337(4) 0.02974(11) Uani 1 1 d . . . . .
F1 F 0.44447(6) 0.42914(9) 0.05618(12) 0.0485(3) Uani 1 1 d . . . . .
O1 O 0.11654(7) 1.06586(10) -0.05318(13) 0.0382(3) Uani 1 1 d . . . . .
O2 O 0.32221(7) 1.01612(9) -0.03766(12) 0.0315(3) Uani 1 1 d . . . . .
O3 O 0.41535(7) 0.84585(10) 0.16297(11) 0.0343(3) Uani 1 1 d . . . . .
O4 O 0.43866(6) 0.87785(10) -0.04283(11) 0.0303(3) Uani 1 1 d . . . . .
N1 N 0.17376(7) 0.74638(10) 0.05851(13) 0.0241(3) Uani 1 1 d . . . . .
N2 N -0.02307(9) 0.81306(16) -0.18424(18) 0.0488(4) Uani 1 1 d . . . . .
C1 C 0.39692(9) 0.51184(13) 0.05413(18) 0.0310(4) Uani 1 1 d . . . . .
C2 C 0.38763(9) 0.57542(14) -0.05441(17) 0.0310(4) Uani 1 1 d . . . . .
H2 H 0.4140 0.5633 -0.1242 0.037 Uiso 1 1 calc R . . . .
C3 C 0.33778(9) 0.65828(13) -0.05718(16) 0.0259(3) Uani 1 1 d . . . . .
H3 H 0.3304 0.7024 -0.1297 0.031 Uiso 1 1 calc R . . . .
C4 C 0.29871(8) 0.67571(12) 0.04807(15) 0.0227(3) Uani 1 1 d . . . . .
C5 C 0.31013(9) 0.60886(13) 0.15649(16) 0.0270(3) Uani 1 1 d . . . . .
H5 H 0.2840 0.6199 0.2269 0.032 Uiso 1 1 calc R . . . .
C6 C 0.35987(9) 0.52646(14) 0.16016(17) 0.0301(4) Uani 1 1 d . . . . .
H6 H 0.3680 0.4822 0.2325 0.036 Uiso 1 1 calc R . . . .
C7 C 0.24637(8) 0.76419(12) 0.04762(15) 0.0225(3) Uani 1 1 d . . . . .
C8 C 0.25619(8) 0.87298(12) 0.03532(15) 0.0227(3) Uani 1 1 d . . . . .
C9 C 0.18615(9) 0.92256(13) 0.03718(15) 0.0238(3) Uani 1 1 d . . . . .
C10 C 0.13684(9) 0.84307(13) 0.05092(16) 0.0250(3) Uani 1 1 d . . . . .
C11 C 0.00527(9) 0.83077(14) -0.08119(18) 0.0315(4) Uani 1 1 d . . . . .
C12 C 0.13991(8) 0.64259(13) 0.04521(16) 0.0246(3) Uani 1 1 d . . . . .
C13 C 0.13071(10) 0.59744(15) -0.07731(17) 0.0329(4) Uani 1 1 d . . . . .
H13 H 0.1443 0.6344 -0.1484 0.040 Uiso 1 1 calc R . . . .
C14 C 0.10121(11) 0.49684(16) -0.0935(2) 0.0417(5) Uani 1 1 d . . . . .
H14 H 0.0948 0.4657 -0.1757 0.050 Uiso 1 1 calc R . . . .
C15 C 0.08126(10) 0.44278(15) 0.0126(2) 0.0426(5) Uani 1 1 d . . . . .
H15 H 0.0615 0.3750 0.0018 0.051 Uiso 1 1 calc R . . . .
C16 C 0.09039(10) 0.48848(16) 0.1342(2) 0.0433(5) Uani 1 1 d . . . . .
H16 H 0.0766 0.4514 0.2051 0.052 Uiso 1 1 calc R . . . .
C17 C 0.11999(10) 0.58957(15) 0.15207(18) 0.0337(4) Uani 1 1 d . . . . .
H17 H 0.1262 0.6207 0.2343 0.040 Uiso 1 1 calc R . . . .
C18 C 0.16704(9) 1.03782(13) 0.02704(16) 0.0258(3) Uani 1 1 d . . . . .
C19 C 0.20761(9) 1.11389(13) 0.11911(16) 0.0256(3) Uani 1 1 d . . . . .
C20 C 0.20136(10) 1.22212(14) 0.0910(2) 0.0349(4) Uani 1 1 d . . . . .
H20 H 0.1736 1.2449 0.0148 0.042 Uiso 1 1 calc R . . . .
C21 C 0.23633(11) 1.29510(15) 0.1764(2) 0.0436(5) Uani 1 1 d . . . . .
H21 H 0.2328 1.3670 0.1568 0.052 Uiso 1 1 calc R . . . .
C22 C 0.27648(11) 1.26212(16) 0.2906(2) 0.0438(5) Uani 1 1 d . . . . .
H22 H 0.2994 1.3119 0.3483 0.053 Uiso 1 1 calc R . . . .
C23 C 0.28281(12) 1.15535(16) 0.31957(19) 0.0410(5) Uani 1 1 d . . . . .
H23 H 0.3099 1.1333 0.3968 0.049 Uiso 1 1 calc R . . . .
C24 C 0.24880(10) 1.08124(14) 0.23376(17) 0.0311(4) Uani 1 1 d . . . . .
H24 H 0.2536 1.0093 0.2530 0.037 Uiso 1 1 calc R . . . .
C25 C 0.32287(9) 0.92808(12) 0.01086(15) 0.0230(3) Uani 1 1 d . . . . .
C26 C 0.39754(9) 0.87669(12) 0.05394(16) 0.0245(3) Uani 1 1 d . . . . .
C27 C 0.51271(9) 0.83428(16) -0.01356(19) 0.0365(4) Uani 1 1 d . . . . .
H27A H 0.5108 0.7632 0.0219 0.044 Uiso 1 1 calc R . . . .
H27B H 0.5420 0.8785 0.0497 0.044 Uiso 1 1 calc R . . . .
C28 C 0.54529(11) 0.83209(19) -0.1396(2) 0.0496(5) Uani 1 1 d . . . . .
H28A H 0.5164 0.7870 -0.2006 0.074 Uiso 1 1 calc GR . . . .
H28B H 0.5945 0.8053 -0.1245 0.074 Uiso 1 1 calc GR . . . .
H28C H 0.5459 0.9026 -0.1745 0.074 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 C10 1.7647(17) . ?
S1 C11 1.689(2) . ?
F1 C1 1.3591(19) . ?
O1 C18 1.219(2) . ?
O2 C25 1.2174(19) . ?
O3 C26 1.199(2) . ?
O4 C26 1.3253(19) . ?
O4 C27 1.465(2) . ?
N1 C7 1.372(2) . ?
N1 C10 1.393(2) . ?
N1 C12 1.448(2) . ?
N2 C11 1.148(2) . ?
C1 C2 1.372(2) . ?
C1 C6 1.371(2) . ?
C2 H2 0.9300 . ?
C2 C3 1.388(2) . ?
C3 H3 0.9300 . ?
C3 C4 1.392(2) . ?
C4 C5 1.397(2) . ?
C4 C7 1.473(2) . ?
C5 H5 0.9300 . ?
C5 C6 1.381(2) . ?
C6 H6 0.9300 . ?
C7 C8 1.391(2) . ?
C8 C9 1.434(2) . ?
C8 C25 1.458(2) . ?
C9 C10 1.370(2) . ?
C9 C18 1.496(2) . ?
C12 C13 1.379(2) . ?
C12 C17 1.378(2) . ?
C13 H13 0.9300 . ?
C13 C14 1.382(3) . ?
C14 H14 0.9300 . ?
C14 C15 1.378(3) . ?
C15 H15 0.9300 . ?
C15 C16 1.374(3) . ?
C16 H16 0.9300 . ?
C16 C17 1.389(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.486(2) . ?
C19 C20 1.397(2) . ?
C19 C24 1.388(2) . ?
C20 H20 0.9300 . ?
C20 C21 1.378(3) . ?
C21 H21 0.9300 . ?
C21 C22 1.377(3) . ?
C22 H22 0.9300 . ?
C22 C23 1.381(3) . ?
C23 H23 0.9300 . ?
C23 C24 1.384(3) . ?
C24 H24 0.9300 . ?
C25 C26 1.534(2) . ?
C27 H27A 0.9700 . ?
C27 H27B 0.9700 . ?
C27 C28 1.499(3) . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?

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
C11 S1 C10 99.27(8) . . ?
C26 O4 C27 116.21(13) . . ?
C7 N1 C10 108.93(13) . . ?
C7 N1 C12 123.45(13) . . ?
C10 N1 C12 125.79(13) . . ?
F1 C1 C2 118.45(16) . . ?
F1 C1 C6 118.17(16) . . ?
C6 C1 C2 123.38(16) . . ?
C1 C2 H2 120.9 . . ?
C1 C2 C3 118.19(16) . . ?
C3 C2 H2 120.9 . . ?
C2 C3 H3 119.8 . . ?
C2 C3 C4 120.35(15) . . ?
C4 C3 H3 119.8 . . ?
C3 C4 C5 119.33(15) . . ?
C3 C4 C7 121.09(14) . . ?
C5 C4 C7 119.57(14) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 C4 120.65(15) . . ?
C6 C5 H5 119.7 . . ?
C1 C6 C5 118.10(16) . . ?
C1 C6 H6 121.0 . . ?
C5 C6 H6 121.0 . . ?
N1 C7 C4 121.17(14) . . ?
N1 C7 C8 107.90(13) . . ?
C8 C7 C4 130.92(14) . . ?
C7 C8 C9 107.57(14) . . ?
C7 C8 C25 127.37(14) . . ?
C9 C8 C25 124.77(14) . . ?
C8 C9 C18 128.78(15) . . ?
C10 C9 C8 106.80(14) . . ?
C10 C9 C18 124.42(14) . . ?
N1 C10 S1 122.31(12) . . ?
C9 C10 S1 128.60(12) . . ?
C9 C10 N1 108.79(14) . . ?
N2 C11 S1 177.17(18) . . ?
C13 C12 N1 117.57(14) . . ?
C17 C12 N1 121.03(15) . . ?
C17 C12 C13 121.36(16) . . ?
C12 C13 H13 120.3 . . ?
C12 C13 C14 119.50(17) . . ?
C14 C13 H13 120.3 . . ?
C13 C14 H14 120.1 . . ?
C15 C14 C13 119.75(19) . . ?
C15 C14 H14 120.1 . . ?
C14 C15 H15 119.8 . . ?
C16 C15 C14 120.38(18) . . ?
C16 C15 H15 119.8 . . ?
C15 C16 H16 119.7 . . ?
C15 C16 C17 120.55(18) . . ?
C17 C16 H16 119.7 . . ?
C12 C17 C16 118.47(18) . . ?
C12 C17 H17 120.8 . . ?
C16 C17 H17 120.8 . . ?
O1 C18 C9 118.83(15) . . ?
O1 C18 C19 121.94(15) . . ?
C19 C18 C9 119.16(14) . . ?
C20 C19 C18 118.40(16) . . ?
C24 C19 C18 122.25(15) . . ?
C24 C19 C20 119.30(16) . . ?
C19 C20 H20 120.0 . . ?
C21 C20 C19 119.95(18) . . ?
C21 C20 H20 120.0 . . ?
C20 C21 H21 119.8 . . ?
C22 C21 C20 120.39(18) . . ?
C22 C21 H21 119.8 . . ?
C21 C22 H22 119.9 . . ?
C21 C22 C23 120.14(18) . . ?
C23 C22 H22 119.9 . . ?
C22 C23 H23 120.0 . . ?
C22 C23 C24 120.00(19) . . ?
C24 C23 H23 120.0 . . ?
C19 C24 H24 119.9 . . ?
C23 C24 C19 120.21(17) . . ?
C23 C24 H24 119.9 . . ?
O2 C25 C8 122.67(15) . . ?
O2 C25 C26 117.92(14) . . ?
C8 C25 C26 119.34(13) . . ?
O3 C26 O4 126.67(15) . . ?
O3 C26 C25 122.78(14) . . ?
O4 C26 C25 110.44(14) . . ?
O4 C27 H27A 110.4 . . ?
O4 C27 H27B 110.4 . . ?
O4 C27 C28 106.71(16) . . ?
H27A C27 H27B 108.6 . . ?
C28 C27 H27A 110.4 . . ?
C28 C27 H27B 110.4 . . ?
C27 C28 H28A 109.5 . . ?
C27 C28 H28B 109.5 . . ?
C27 C28 H28C 109.5 . . ?
H28A C28 H28B 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 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
F1 C1 C2 C3 178.56(15) . . . . ?
F1 C1 C6 C5 -178.33(16) . . . . ?
O1 C18 C19 C20 -17.3(2) . . . . ?
O1 C18 C19 C24 160.07(17) . . . . ?
O2 C25 C26 O3 124.16(18) . . . . ?
O2 C25 C26 O4 -52.30(19) . . . . ?
N1 C7 C8 C9 -0.78(18) . . . . ?
N1 C7 C8 C25 -174.73(14) . . . . ?
N1 C12 C13 C14 177.56(16) . . . . ?
N1 C12 C17 C16 -177.49(15) . . . . ?
C1 C2 C3 C4 0.1(3) . . . . ?
C2 C1 C6 C5 0.7(3) . . . . ?
C2 C3 C4 C5 -0.1(2) . . . . ?
C2 C3 C4 C7 179.10(15) . . . . ?
C3 C4 C5 C6 0.3(2) . . . . ?
C3 C4 C7 N1 120.44(17) . . . . ?
C3 C4 C7 C8 -58.4(2) . . . . ?
C4 C5 C6 C1 -0.6(3) . . . . ?
C4 C7 C8 C9 178.17(16) . . . . ?
C4 C7 C8 C25 4.2(3) . . . . ?
C5 C4 C7 N1 -60.4(2) . . . . ?
C5 C4 C7 C8 120.79(19) . . . . ?
C6 C1 C2 C3 -0.5(3) . . . . ?
C7 N1 C10 S1 -175.10(11) . . . . ?
C7 N1 C10 C9 -0.90(18) . . . . ?
C7 N1 C12 C13 -70.1(2) . . . . ?
C7 N1 C12 C17 107.73(19) . . . . ?
C7 C4 C5 C6 -178.87(15) . . . . ?
C7 C8 C9 C10 0.23(18) . . . . ?
C7 C8 C9 C18 -179.97(16) . . . . ?
C7 C8 C25 O2 156.60(16) . . . . ?
C7 C8 C25 C26 -26.7(2) . . . . ?
C8 C9 C10 S1 174.12(12) . . . . ?
C8 C9 C10 N1 0.40(18) . . . . ?
C8 C9 C18 O1 128.59(18) . . . . ?
C8 C9 C18 C19 -54.4(2) . . . . ?
C8 C25 C26 O3 -52.7(2) . . . . ?
C8 C25 C26 O4 130.86(15) . . . . ?
C9 C8 C25 O2 -16.4(2) . . . . ?
C9 C8 C25 C26 160.32(15) . . . . ?
C9 C18 C19 C20 165.77(15) . . . . ?
C9 C18 C19 C24 -16.8(2) . . . . ?
C10 N1 C7 C4 -178.04(14) . . . . ?
C10 N1 C7 C8 1.04(18) . . . . ?
C10 N1 C12 C13 92.76(19) . . . . ?
C10 N1 C12 C17 -89.4(2) . . . . ?
C10 C9 C18 O1 -51.6(2) . . . . ?
C10 C9 C18 C19 125.36(17) . . . . ?
C11 S1 C10 N1 -87.27(14) . . . . ?
C11 S1 C10 C9 99.76(17) . . . . ?
C12 N1 C7 C4 -12.7(2) . . . . ?
C12 N1 C7 C8 166.41(14) . . . . ?
C12 N1 C10 S1 20.0(2) . . . . ?
C12 N1 C10 C9 -165.84(15) . . . . ?
C12 C13 C14 C15 0.1(3) . . . . ?
C13 C12 C17 C16 0.3(3) . . . . ?
C13 C14 C15 C16 0.2(3) . . . . ?
C14 C15 C16 C17 -0.2(3) . . . . ?
C15 C16 C17 C12 0.0(3) . . . . ?
C17 C12 C13 C14 -0.3(3) . . . . ?
C18 C9 C10 S1 -5.7(3) . . . . ?
C18 C9 C10 N1 -179.41(15) . . . . ?
C18 C19 C20 C21 177.91(16) . . . . ?
C18 C19 C24 C23 -176.91(16) . . . . ?
C19 C20 C21 C22 -1.1(3) . . . . ?
C20 C19 C24 C23 0.5(3) . . . . ?
C20 C21 C22 C23 0.9(3) . . . . ?
C21 C22 C23 C24 0.0(3) . . . . ?
C22 C23 C24 C19 -0.7(3) . . . . ?
C24 C19 C20 C21 0.4(3) . . . . ?
C25 C8 C9 C10 174.38(15) . . . . ?
C25 C8 C9 C18 -5.8(3) . . . . ?
C26 O4 C27 C28 173.52(15) . . . . ?
C27 O4 C26 O3 1.7(2) . . . . ?
C27 O4 C26 C25 177.99(13) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
