# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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. 
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data_mo_gb032_0m
_database_code_depnum_ccdc_archive 'CCDC 1877446'
loop_
_audit_author_name
_audit_author_address
'Giorgio Baggi'
;University of Windsor
Canada
;
_audit_update_record             
;
2018-11-06 deposited with the CCDC.	2019-04-09 downloaded from the CCDC.
;
_audit_creation_date             2018-10-16
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3

# start Validation Reply Form
_vrf_PLAT411_mo_gb032_0m         
;
PROBLEM: Short Inter H...H Contact H10 ..H17A . 1.67 Ang.
RESPONSE: Due to disorder of the benzothiophene fragment.
;
# end Validation Reply Form

_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C27 H21 N2 S2, B F4'
_chemical_formula_sum            'C27 H21 B F4 N2 S2'
_chemical_formula_weight         524.39
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 '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'
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                   9.1113(4)
_cell_length_b                   14.2082(7)
_cell_length_c                   19.2241(8)
_cell_angle_alpha                90
_cell_angle_beta                 95.410(2)
_cell_angle_gamma                90
_cell_volume                     2477.57(19)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9757
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      28.16
_cell_measurement_theta_min      2.95
_shelx_estimated_absorpt_T_max   0.985
_shelx_estimated_absorpt_T_min   0.901
_exptl_absorpt_coefficient_mu    0.265
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.7003
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0650 before and 0.0609 after correction. The Ratio of minimum to maximum transmission is 0.9391. The λ/2 correction factor is 0.00150.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            white
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.406
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Needle
_exptl_crystal_F_000             1080
_exptl_crystal_size_max          0.402
_exptl_crystal_size_mid          0.086
_exptl_crystal_size_min          0.059
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0725
_diffrn_reflns_av_unetI/netI     0.0228
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            116870
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.354
_diffrn_reflns_theta_min         2.867
_diffrn_ambient_temperature      170.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.995
_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_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4793
_reflns_number_total             6152
_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, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         0.485
_refine_diff_density_min         -0.511
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     420
_refine_ls_number_reflns         6152
_refine_ls_number_restraints     146
_refine_ls_R_factor_all          0.0676
_refine_ls_R_factor_gt           0.0467
_refine_ls_restrained_S_all      1.055
_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)+(0.0391P)²+1.8264P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1024
_refine_ls_wR_factor_ref         0.1130
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
B1A \\sim F1 \\sim B1 \\sim F2 \\sim F3 \\sim F4 \\sim F3A \\sim F1A \\sim F2A:
within 2A with sigma of 0.04 and sigma for terminal atoms of 0.08
Uanis(C13) = Uanis(C13A)
Uanis(C18) = Uanis(C18A)
Uanis(C15) = Uanis(C15A)
Uanis(C19) = Uanis(C19A)
Uanis(C21) = Uanis(C21A)
Uanis(C14) = Uanis(C14A)
3. Same fragment restrains
{C20A, C19A, C13A, C14A, C15A, C16A, C17A, C21A, C18A, S1A} sigma for 1-2:
0.02, 1-3: 0.02
as
{C20, C19, C13, C14, C15, C16, C17, C21, C18, S1}
4. Others
 Sof(F3A)=Sof(F1A)=Sof(F2A)=Sof(B1A)=1-FVAR(1)
 Sof(F1)=Sof(F2)=Sof(F3)=Sof(B1)=FVAR(1)
 Sof(C20A)=Sof(H20D)=Sof(H20E)=Sof(H20F)=Sof(C19A)=Sof(C13A)=Sof(C14A)=
 Sof(C15A)=Sof(H15A)=Sof(C16A)=Sof(H16A)=Sof(C17A)=Sof(H17A)=Sof(C21A)=
 Sof(H21A)=Sof(C18A)=Sof(S1A)=1-FVAR(2)
 Sof(C20)=Sof(H20A)=Sof(H20B)=Sof(H20C)=Sof(C19)=Sof(C13)=Sof(C14)=Sof(C15)=
 Sof(H15)=Sof(C16)=Sof(H16)=Sof(C17)=Sof(H17)=Sof(C21)=Sof(H21)=Sof(C18)=
 Sof(S1)=FVAR(2)
5.a Aromatic/amide H refined with riding coordinates:
 C15(H15), C16(H16), C17(H17), C21(H21), N1(H1), N2(H2), C1(H1A), C2(H2A),
 C3(H3), C9(H9), C10(H10), C11(H11), C25(H25), C26(H26), C27(H27), C15A(H15A),
 C16A(H16A), C17A(H17A), C21A(H21A)
5.b Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C23(H23A,H23B,H23C), C20A(H20D,H20E,H20F)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_special_details      
;
The structure was solved using Direct Methods (ShelXS). RE = 0.2, Nqual =  -1, Ralpha = 0.079
;
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
C20 C -0.1699(3) 0.34063(19) 0.72044(12) 0.0447(6) Uani 0.9371(17) 1 d D . P A
1
H20A H -0.264532 0.368198 0.730031 0.067 Uiso 0.9371(17) 1 calc GR . P A 1
H20B H -0.170239 0.328764 0.670205 0.067 Uiso 0.9371(17) 1 calc GR . P A 1
H20C H -0.089994 0.384342 0.735509 0.067 Uiso 0.9371(17) 1 calc GR . P A 1
C19 C -0.1471(2) 0.25012(17) 0.75938(11) 0.0315(4) Uani 0.9371(17) 1 d D . P A
1
C13 C -0.0559(2) 0.23006(14) 0.81806(10) 0.0265(4) Uani 0.9371(17) 1 d D . P A
1
C14 C -0.06304(19) 0.13264(14) 0.83890(10) 0.0272(4) Uani 0.9371(17) 1 d D . P
A 1
C15 C 0.0124(2) 0.08532(15) 0.89546(11) 0.0305(4) Uani 0.9371(17) 1 d D . P A 1
H15 H 0.082581 0.117674 0.926391 0.037 Uiso 0.9371(17) 1 calc R . P A 1
C16 C -0.0165(2) -0.00890(16) 0.90573(12) 0.0401(5) Uani 0.9371(17) 1 d D . P A
1
H16 H 0.035131 -0.041337 0.943730 0.048 Uiso 0.9371(17) 1 calc R . P A 1
C17 C -0.1205(3) -0.05710(17) 0.86108(15) 0.0481(6) Uani 0.9371(17) 1 d D . P A
1
H17 H -0.140249 -0.121434 0.869913 0.058 Uiso 0.9371(17) 1 calc R . P A 1
C21 C -0.1949(2) -0.01300(16) 0.80442(13) 0.0423(5) Uani 0.9371(17) 1 d D . P A
1
H21 H -0.264688 -0.046205 0.773810 0.051 Uiso 0.9371(17) 1 calc R . P A 1
C18 C -0.1647(2) 0.08208(18) 0.79328(12) 0.0325(5) Uani 0.9371(17) 1 d D . P A
1
S1 S -0.24523(6) 0.15267(5) 0.72741(3) 0.03797(16) Uani 0.9371(17) 1 d D . P A
1
S2 S 0.46379(6) 0.09142(4) 0.83532(3) 0.04624(16) Uani 1 1 d . . . . .
F1 F 0.6947(8) 0.4376(4) 0.8532(4) 0.0436(10) Uani 0.789(18) 1 d . U P B 1
F2 F 0.6054(4) 0.5723(2) 0.8939(3) 0.0664(13) Uani 0.789(18) 1 d . U P B 1
F3 F 0.4631(4) 0.4831(5) 0.81478(18) 0.0604(11) Uani 0.789(18) 1 d . U P B 1
F4 F 0.51049(12) 0.43528(9) 0.92562(6) 0.0418(3) Uani 1 1 d . U . . .
N1 N 0.22165(15) 0.38640(11) 0.90693(8) 0.0264(3) Uani 1 1 d . . . . .
H1 H 0.309248 0.403982 0.925612 0.032 Uiso 1 1 calc R . . . .
N2 N -0.00838(15) 0.38861(11) 0.87167(8) 0.0273(3) Uani 1 1 d . . . . .
H2 H -0.099970 0.408026 0.862911 0.033 Uiso 1 1 calc R . . . .
C1 C 0.0789(2) 0.72261(15) 0.97136(12) 0.0405(5) Uani 1 1 d . . . . .
H1A H 0.074368 0.786260 0.986135 0.049 Uiso 1 1 calc R . . . .
C2 C 0.2044(2) 0.66991(14) 0.98916(11) 0.0370(4) Uani 1 1 d . . . . .
H2A H 0.285627 0.697015 1.016699 0.044 Uiso 1 1 calc R . . . .
C3 C 0.2115(2) 0.57767(14) 0.96680(10) 0.0313(4) Uani 1 1 d . . . . .
H3 H 0.297924 0.541606 0.978865 0.038 Uiso 1 1 calc R . . . .
C4 C 0.09275(18) 0.53740(12) 0.92678(9) 0.0254(3) Uani 1 1 d . . . . .
C5 C 0.10110(17) 0.44055(13) 0.90283(9) 0.0249(3) Uani 1 1 d . . . . .
C6 C 0.18962(19) 0.29884(13) 0.87771(9) 0.0280(4) Uani 1 1 d . . . . .
C7 C 0.30254(19) 0.22572(13) 0.87618(10) 0.0302(4) Uani 1 1 d . . . . .
C8 C 0.39765(19) 0.19830(13) 0.93750(10) 0.0315(4) Uani 1 1 d . . . . .
C9 C 0.4052(2) 0.23187(15) 1.00618(11) 0.0381(4) Uani 1 1 d . . . . .
H9 H 0.342157 0.281466 1.018020 0.046 Uiso 1 1 calc R . . . .
C10 C 0.5049(3) 0.19243(17) 1.05690(13) 0.0477(5) Uani 1 1 d . . . . .
H10 H 0.509202 0.214715 1.103637 0.057 Uiso 1 1 calc R . . . .
C11 C 0.5994(3) 0.12013(16) 1.03979(14) 0.0489(6) Uani 1 1 d . . . . .
H11 H 0.666693 0.093535 1.075148 0.059 Uiso 1 1 calc R . . . .
C12 C 0.04181(19) 0.29985(13) 0.85497(9) 0.0283(4) Uani 1 1 d . . . . .
C22 C 0.3268(2) 0.17543(16) 0.81823(11) 0.0382(5) Uani 1 1 d . . . . .
C23 C 0.2538(3) 0.1853(2) 0.74575(12) 0.0569(7) Uani 1 1 d . . . . .
H23A H 0.174512 0.138793 0.738123 0.085 Uiso 1 1 calc GR . . . .
H23B H 0.326453 0.174878 0.712065 0.085 Uiso 1 1 calc GR . . . .
H23C H 0.212525 0.248781 0.739483 0.085 Uiso 1 1 calc GR . . . .
C24 C 0.4936(2) 0.12503(14) 0.92193(12) 0.0368(4) Uani 1 1 d . . . . .
C25 C 0.5959(2) 0.08732(15) 0.97290(13) 0.0434(5) Uani 1 1 d . . . . .
H25 H 0.662256 0.039498 0.961261 0.052 Uiso 1 1 calc R . . . .
C26 C -0.0344(2) 0.59020(14) 0.90960(11) 0.0351(4) Uani 1 1 d . . . . .
H26 H -0.116508 0.563000 0.882745 0.042 Uiso 1 1 calc R . . . .
C27 C -0.0401(2) 0.68256(15) 0.93199(12) 0.0415(5) Uani 1 1 d . . . . .
H27 H -0.126446 0.718857 0.920244 0.050 Uiso 1 1 calc R . . . .
B1 B 0.5676(9) 0.4831(5) 0.8721(4) 0.0316(14) Uani 0.789(18) 1 d . U P B 1
F3A F 0.4681(16) 0.430(3) 0.8092(8) 0.080(6) Uani 0.211(18) 1 d . U P B 2
F1A F 0.696(3) 0.414(2) 0.8610(17) 0.074(7) Uani 0.211(18) 1 d . U P B 2
F2A F 0.589(2) 0.5579(17) 0.858(2) 0.117(7) Uani 0.211(18) 1 d . U P B 2
B1A B 0.563(4) 0.467(3) 0.859(2) 0.051(8) Uani 0.211(18) 1 d . U P B 2
C20A C 0.102(4) 0.082(2) 0.9324(16) 0.082(19) Uani 0.0629(17) 1 d D . P A 2
H20D H 0.188114 0.054103 0.913402 0.123 Uiso 0.0629(17) 1 calc GR . P A 2
H20E H 0.053279 0.034592 0.959091 0.123 Uiso 0.0629(17) 1 calc GR . P A 2
H20F H 0.134084 0.134715 0.963240 0.123 Uiso 0.0629(17) 1 calc GR . P A 2
C19A C -0.003(3) 0.1174(14) 0.8737(13) 0.0315(4) Uani 0.0629(17) 1 d D . P A 2
C13A C -0.017(3) 0.2077(12) 0.8480(12) 0.0265(4) Uani 0.0629(17) 1 d D . P A 2
C14A C -0.119(3) 0.2150(12) 0.7868(12) 0.0272(4) Uani 0.0629(17) 1 d D . P A 2
C15A C -0.160(3) 0.2916(14) 0.7449(14) 0.0305(4) Uani 0.0629(17) 1 d D . P A 2
H15A H -0.116044 0.351378 0.754827 0.037 Uiso 0.0629(17) 1 calc R . P A 2
C16A C -0.265(4) 0.2809(17) 0.6886(17) 0.065(13) Uani 0.0629(17) 1 d D . P A 2
H16A H -0.293473 0.333730 0.660214 0.078 Uiso 0.0629(17) 1 calc R . P A 2
C17A C -0.329(4) 0.1929(19) 0.6730(16) 0.067(14) Uani 0.0629(17) 1 d D . P A 2
H17A H -0.408911 0.188309 0.637847 0.081 Uiso 0.0629(17) 1 calc R . P A 2
C21A C -0.278(3) 0.1130(15) 0.7077(14) 0.0423(5) Uani 0.0629(17) 1 d D . P A 2
H21A H -0.305528 0.052143 0.690720 0.051 Uiso 0.0629(17) 1 calc R . P A 2
C18A C -0.183(3) 0.1242(12) 0.7690(12) 0.0325(5) Uani 0.0629(17) 1 d D . P A 2
S1A S -0.1131(14) 0.0394(8) 0.8260(7) 0.070(4) Uani 0.0629(17) 1 d D . P 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
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C20 C19 1.493(3) . ?
C19 C13 1.367(3) . ?
C19 S1 1.729(2) . ?
C13 C14 1.444(3) . ?
C13 C12 1.470(3) . ?
C14 C15 1.402(3) . ?
C14 C18 1.411(3) . ?
C15 H15 0.9500 . ?
C15 C16 1.382(3) . ?
C16 H16 0.9500 . ?
C16 C17 1.396(3) . ?
C17 H17 0.9500 . ?
C17 C21 1.378(3) . ?
C21 H21 0.9500 . ?
C21 C18 1.399(3) . ?
C18 S1 1.724(3) . ?
S2 C22 1.736(2) . ?
S2 C24 1.729(2) . ?
F1 B1 1.404(11) . ?
F2 B1 1.369(8) . ?
F3 B1 1.387(8) . ?
F4 B1 1.375(9) . ?
F4 B1A 1.48(3) . ?
N1 H1 0.8800 . ?
N1 C5 1.337(2) . ?
N1 C6 1.385(2) . ?
N2 H2 0.8800 . ?
N2 C5 1.336(2) . ?
N2 C12 1.389(2) . ?
C1 H1A 0.9500 . ?
C1 C2 1.382(3) . ?
C1 C27 1.385(3) . ?
C2 H2A 0.9500 . ?
C2 C3 1.383(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.390(3) . ?
C4 C5 1.455(3) . ?
C4 C26 1.394(2) . ?
C6 C7 1.464(2) . ?
C6 C12 1.376(2) . ?
C7 C8 1.449(3) . ?
C7 C22 1.359(3) . ?
C8 C9 1.399(3) . ?
C8 C24 1.410(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.387(3) . ?
C10 H10 0.9500 . ?
C10 C11 1.399(3) . ?
C11 H11 0.9500 . ?
C11 C25 1.365(3) . ?
C12 C13A 1.416(16) . ?
C22 C23 1.493(3) . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 C25 1.394(3) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
C26 C27 1.384(3) . ?
C27 H27 0.9500 . ?
F3A B1A 1.33(4) . ?
F1A B1A 1.42(5) . ?
F2A B1A 1.31(4) . ?
C20A H20D 0.9800 . ?
C20A H20E 0.9800 . ?
C20A H20F 0.9800 . ?
C20A C19A 1.499(15) . ?
C19A C13A 1.376(16) . ?
C19A S1A 1.702(16) . ?
C13A C14A 1.432(14) . ?
C14A C15A 1.383(15) . ?
C14A C18A 1.444(15) . ?
C15A H15A 0.9500 . ?
C15A C16A 1.383(16) . ?
C16A H16A 0.9500 . ?
C16A C17A 1.400(17) . ?
C17A H17A 0.9500 . ?
C17A C21A 1.376(17) . ?
C21A H21A 0.9500 . ?
C21A C18A 1.402(15) . ?
C18A S1A 1.710(14) . ?

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
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
C20 C19 S1 117.96(15) . . ?
C13 C19 C20 129.7(2) . . ?
C13 C19 S1 112.34(18) . . ?
C19 C13 C14 112.89(18) . . ?
C19 C13 C12 123.45(19) . . ?
C14 C13 C12 123.64(17) . . ?
C15 C14 C13 130.03(18) . . ?
C15 C14 C18 118.9(2) . . ?
C18 C14 C13 111.09(18) . . ?
C14 C15 H15 120.3 . . ?
C16 C15 C14 119.3(2) . . ?
C16 C15 H15 120.3 . . ?
C15 C16 H16 119.5 . . ?
C15 C16 C17 121.0(2) . . ?
C17 C16 H16 119.5 . . ?
C16 C17 H17 119.4 . . ?
C21 C17 C16 121.2(2) . . ?
C21 C17 H17 119.4 . . ?
C17 C21 H21 121.0 . . ?
C17 C21 C18 118.1(2) . . ?
C18 C21 H21 121.0 . . ?
C14 C18 S1 111.67(18) . . ?
C21 C18 C14 121.6(2) . . ?
C21 C18 S1 126.72(17) . . ?
C18 S1 C19 92.00(10) . . ?
C24 S2 C22 92.14(10) . . ?
C5 N1 H1 124.7 . . ?
C5 N1 C6 110.64(14) . . ?
C6 N1 H1 124.7 . . ?
C5 N2 H2 124.5 . . ?
C5 N2 C12 110.91(14) . . ?
C12 N2 H2 124.5 . . ?
C2 C1 H1A 120.0 . . ?
C2 C1 C27 120.0(2) . . ?
C27 C1 H1A 120.0 . . ?
C1 C2 H2A 120.1 . . ?
C1 C2 C3 119.88(19) . . ?
C3 C2 H2A 120.1 . . ?
C2 C3 H3 119.8 . . ?
C2 C3 C4 120.37(17) . . ?
C4 C3 H3 119.8 . . ?
C3 C4 C5 120.21(16) . . ?
C3 C4 C26 119.72(18) . . ?
C26 C4 C5 120.07(17) . . ?
N1 C5 C4 126.33(16) . . ?
N2 C5 N1 106.44(16) . . ?
N2 C5 C4 127.22(15) . . ?
N1 C6 C7 121.59(15) . . ?
C12 C6 N1 106.38(15) . . ?
C12 C6 C7 132.02(18) . . ?
C8 C7 C6 122.81(17) . . ?
C22 C7 C6 123.93(18) . . ?
C22 C7 C8 113.24(17) . . ?
C9 C8 C7 130.40(18) . . ?
C9 C8 C24 118.42(18) . . ?
C24 C8 C7 111.17(18) . . ?
C8 C9 H9 120.1 . . ?
C10 C9 C8 119.7(2) . . ?
C10 C9 H9 120.1 . . ?
C9 C10 H10 119.7 . . ?
C9 C10 C11 120.5(2) . . ?
C11 C10 H10 119.7 . . ?
C10 C11 H11 119.6 . . ?
C25 C11 C10 120.8(2) . . ?
C25 C11 H11 119.6 . . ?
N2 C12 C13 121.77(15) . . ?
N2 C12 C13A 136.9(11) . . ?
C6 C12 C13 132.55(17) . . ?
C6 C12 N2 105.64(16) . . ?
C6 C12 C13A 111.8(9) . . ?
C7 C22 S2 112.07(16) . . ?
C7 C22 C23 128.6(2) . . ?
C23 C22 S2 119.37(16) . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C8 C24 S2 111.35(15) . . ?
C25 C24 S2 127.21(17) . . ?
C25 C24 C8 121.4(2) . . ?
C11 C25 C24 119.0(2) . . ?
C11 C25 H25 120.5 . . ?
C24 C25 H25 120.5 . . ?
C4 C26 H26 120.3 . . ?
C27 C26 C4 119.43(19) . . ?
C27 C26 H26 120.3 . . ?
C1 C27 H27 119.7 . . ?
C26 C27 C1 120.62(18) . . ?
C26 C27 H27 119.7 . . ?
F2 B1 F1 108.4(6) . . ?
F2 B1 F3 112.1(5) . . ?
F2 B1 F4 109.4(6) . . ?
F3 B1 F1 108.3(6) . . ?
F4 B1 F1 110.3(6) . . ?
F4 B1 F3 108.4(6) . . ?
F3A B1A F4 105(2) . . ?
F3A B1A F1A 108(3) . . ?
F1A B1A F4 99(3) . . ?
F2A B1A F4 112(3) . . ?
F2A B1A F3A 119(3) . . ?
F2A B1A F1A 111(3) . . ?
H20D C20A H20E 109.5 . . ?
H20D C20A H20F 109.5 . . ?
H20E C20A H20F 109.5 . . ?
C19A C20A H20D 109.5 . . ?
C19A C20A H20E 109.5 . . ?
C19A C20A H20F 109.5 . . ?
C20A C19A S1A 119.4(14) . . ?
C13A C19A C20A 127.7(15) . . ?
C13A C19A S1A 112.6(9) . . ?
C12 C13A C14A 102.7(11) . . ?
C19A C13A C12 143.8(13) . . ?
C19A C13A C14A 113.1(11) . . ?
C13A C14A C18A 110.2(10) . . ?
C15A C14A C13A 130.8(13) . . ?
C15A C14A C18A 118.9(11) . . ?
C14A C15A H15A 120.1 . . ?
C14A C15A C16A 119.9(14) . . ?
C16A C15A H15A 120.1 . . ?
C15A C16A H16A 119.7 . . ?
C15A C16A C17A 120.6(14) . . ?
C17A C16A H16A 119.7 . . ?
C16A C17A H17A 119.4 . . ?
C21A C17A C16A 121.2(14) . . ?
C21A C17A H17A 119.4 . . ?
C17A C21A H21A 121.1 . . ?
C17A C21A C18A 117.8(14) . . ?
C18A C21A H21A 121.1 . . ?
C14A C18A S1A 111.1(8) . . ?
C21A C18A C14A 120.3(12) . . ?
C21A C18A S1A 128.3(12) . . ?
C19A S1A C18A 92.9(7) . . ?

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
C20 C19 C13 C14 -178.6(2) . . . . ?
C20 C19 C13 C12 0.0(3) . . . . ?
C20 C19 S1 C18 179.09(18) . . . . ?
C19 C13 C14 C15 -179.9(2) . . . . ?
C19 C13 C14 C18 -0.6(2) . . . . ?
C19 C13 C12 N2 47.8(3) . . . . ?
C19 C13 C12 C6 -129.7(2) . . . . ?
C13 C19 S1 C18 0.11(17) . . . . ?
C13 C14 C15 C16 178.2(2) . . . . ?
C13 C14 C18 C21 -177.52(19) . . . . ?
C13 C14 C18 S1 0.6(2) . . . . ?
C14 C13 C12 N2 -133.78(19) . . . . ?
C14 C13 C12 C6 48.8(3) . . . . ?
C14 C15 C16 C17 -0.6(3) . . . . ?
C14 C18 S1 C19 -0.43(16) . . . . ?
C15 C14 C18 C21 1.9(3) . . . . ?
C15 C14 C18 S1 -179.94(15) . . . . ?
C15 C16 C17 C21 1.6(4) . . . . ?
C16 C17 C21 C18 -0.8(4) . . . . ?
C17 C21 C18 C14 -1.0(3) . . . . ?
C17 C21 C18 S1 -178.82(19) . . . . ?
C21 C18 S1 C19 177.6(2) . . . . ?
C18 C14 C15 C16 -1.1(3) . . . . ?
S1 C19 C13 C14 0.2(2) . . . . ?
S1 C19 C13 C12 178.82(14) . . . . ?
S2 C24 C25 C11 -177.07(18) . . . . ?
N1 C6 C7 C8 50.1(3) . . . . ?
N1 C6 C7 C22 -131.5(2) . . . . ?
N1 C6 C12 C13 177.79(19) . . . . ?
N1 C6 C12 N2 0.03(19) . . . . ?
N1 C6 C12 C13A -158.2(11) . . . . ?
N2 C12 C13A C19A -119(4) . . . . ?
N2 C12 C13A C14A 69(2) . . . . ?
C1 C2 C3 C4 -0.3(3) . . . . ?
C2 C1 C27 C26 -0.6(3) . . . . ?
C2 C3 C4 C5 179.46(17) . . . . ?
C2 C3 C4 C26 -0.5(3) . . . . ?
C3 C4 C5 N1 -9.9(3) . . . . ?
C3 C4 C5 N2 171.19(17) . . . . ?
C3 C4 C26 C27 0.8(3) . . . . ?
C4 C26 C27 C1 -0.2(3) . . . . ?
C5 N1 C6 C7 -179.34(16) . . . . ?
C5 N1 C6 C12 -0.2(2) . . . . ?
C5 N2 C12 C13 -177.86(16) . . . . ?
C5 N2 C12 C6 0.2(2) . . . . ?
C5 N2 C12 C13A 149.9(12) . . . . ?
C5 C4 C26 C27 -179.19(18) . . . . ?
C6 N1 C5 N2 0.36(19) . . . . ?
C6 N1 C5 C4 -178.75(16) . . . . ?
C6 C7 C8 C9 -0.5(3) . . . . ?
C6 C7 C8 C24 178.57(17) . . . . ?
C6 C7 C22 S2 -177.68(15) . . . . ?
C6 C7 C22 C23 3.2(4) . . . . ?
C6 C12 C13A C19A 30(5) . . . . ?
C6 C12 C13A C14A -142.4(16) . . . . ?
C7 C6 C12 C13 -3.2(4) . . . . ?
C7 C6 C12 N2 179.00(19) . . . . ?
C7 C6 C12 C13A 20.7(11) . . . . ?
C7 C8 C9 C10 178.6(2) . . . . ?
C7 C8 C24 S2 -0.9(2) . . . . ?
C7 C8 C24 C25 179.72(19) . . . . ?
C8 C7 C22 S2 0.9(2) . . . . ?
C8 C7 C22 C23 -178.2(2) . . . . ?
C8 C9 C10 C11 0.8(3) . . . . ?
C8 C24 C25 C11 2.2(3) . . . . ?
C9 C8 C24 S2 178.31(15) . . . . ?
C9 C8 C24 C25 -1.1(3) . . . . ?
C9 C10 C11 C25 0.4(4) . . . . ?
C10 C11 C25 C24 -1.9(4) . . . . ?
C12 C13 C14 C15 1.5(3) . . . . ?
C12 C13 C14 C18 -179.14(17) . . . . ?
C12 N2 C5 N1 -0.34(19) . . . . ?
C12 N2 C5 C4 178.75(16) . . . . ?
C12 C6 C7 C8 -128.7(2) . . . . ?
C12 C6 C7 C22 49.7(3) . . . . ?
C12 C13A C14A C15A -3(4) . . . . ?
C12 C13A C14A C18A 176(2) . . . . ?
C22 S2 C24 C8 1.16(16) . . . . ?
C22 S2 C24 C25 -179.5(2) . . . . ?
C22 C7 C8 C9 -179.1(2) . . . . ?
C22 C7 C8 C24 0.0(2) . . . . ?
C24 S2 C22 C7 -1.17(17) . . . . ?
C24 S2 C22 C23 178.0(2) . . . . ?
C24 C8 C9 C10 -0.4(3) . . . . ?
C26 C4 C5 N1 170.06(17) . . . . ?
C26 C4 C5 N2 -8.9(3) . . . . ?
C27 C1 C2 C3 0.9(3) . . . . ?
C20A C19A C13A C12 2(7) . . . . ?
C20A C19A C13A C14A 174(3) . . . . ?
C20A C19A S1A C18A -175(3) . . . . ?
C19A C13A C14A C15A -178(4) . . . . ?
C19A C13A C14A C18A 1(4) . . . . ?
C13A C19A S1A C18A 0(3) . . . . ?
C13A C14A C15A C16A -178(3) . . . . ?
C13A C14A C18A C21A -175(3) . . . . ?
C13A C14A C18A S1A -1(3) . . . . ?
C14A C15A C16A C17A -1(6) . . . . ?
C14A C18A S1A C19A 1(3) . . . . ?
C15A C14A C18A C21A 4(5) . . . . ?
C15A C14A C18A S1A 178(3) . . . . ?
C15A C16A C17A C21A -8(7) . . . . ?
C16A C17A C21A C18A 14(6) . . . . ?
C17A C21A C18A C14A -12(5) . . . . ?
C17A C21A C18A S1A 175(3) . . . . ?
C21A C18A S1A C19A 174(3) . . . . ?
C18A C14A C15A C16A 2(5) . . . . ?
S1A C19A C13A C12 -172(3) . . . . ?
S1A C19A C13A C14A -1(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: hexanes ethyl acetate'
####################################################################### 
# 
# 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_mo_gb048_0m
_database_code_depnum_ccdc_archive 'CCDC 1877448'
loop_
_audit_author_name
_audit_author_address
'Giorgio Baggi'
;University of Windsor
Canada
;
_audit_update_record             
;
2018-11-06 deposited with the CCDC.	2019-04-09 downloaded from the CCDC.
;
_audit_creation_date             2018-10-16
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '0.5(C29 H23 N2 O2 S2), C4 H10 O, 0.5(B F4)'
_chemical_formula_sum            'C18.50 H21.50 B0.50 F2 N O2 S'
_chemical_formula_weight         365.33
_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'
B B 0.0013 0.0007 '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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.0211(4)
_cell_length_b                   11.5905(6)
_cell_length_c                   20.2484(11)
_cell_angle_alpha                93.738(2)
_cell_angle_beta                 92.017(2)
_cell_angle_gamma                103.011(2)
_cell_volume                     1827.82(17)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9937
_cell_measurement_temperature    130(2)
_cell_measurement_theta_max      30.54
_cell_measurement_theta_min      2.99
_shelx_estimated_absorpt_T_max   0.980
_shelx_estimated_absorpt_T_min   0.902
_exptl_absorpt_coefficient_mu    0.208
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.7039
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0562 before and 0.0505 after correction. The Ratio of minimum to maximum transmission is 0.9434. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.328
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Needle
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.505
_exptl_crystal_size_mid          0.185
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0403
_diffrn_reflns_av_unetI/netI     0.0200
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            90249
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.588
_diffrn_reflns_theta_min         2.816
_diffrn_ambient_temperature      130.01
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.995
_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_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                9265
_reflns_number_total             11201
_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, 2015)'
_computing_structure_solution    'XM (Sheldrick, 2008)'
_refine_diff_density_max         0.746
_refine_diff_density_min         -0.430
_refine_diff_density_rms         0.058
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     485
_refine_ls_number_reflns         11201
_refine_ls_number_restraints     74
_refine_ls_R_factor_all          0.0627
_refine_ls_R_factor_gt           0.0488
_refine_ls_restrained_S_all      1.053
_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)+(0.0502P)²+1.5706P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1176
_refine_ls_wR_factor_ref         0.1281
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
C2S \\sim C3S \\sim O1S \\sim C4S \\sim C4SA \\sim C5S \\sim C5SA: within 2A
with sigma of 0.04 and sigma for terminal atoms of 0.08
Uanis(F1) = Uanis(F1A)
Uanis(F2) = Uanis(F2A)
Uanis(F3) = Uanis(F3A)
Uanis(F4) = Uanis(F4A)
Uanis(C4S) = Uanis(C4SA)
3. Same fragment restrains
{F2A, F1A, F3A, F4A, B1} sigma for 1-2: 0.02, 1-3: 0.04
as
{F2, F1, F3, F4, B1}
{C2S, C3S, O1S, C4SA, C5SA} sigma for 1-2: 0.02, 1-3: 0.04
as
{C2S, C3S, O1S, C4S, C5S}
4. Others
 Sof(C4SA)=Sof(H4SC)=Sof(H4SD)=Sof(C5SA)=Sof(H5SD)=Sof(H5SE)=Sof(H5SF)=1-FVAR(1)
 Sof(C4S)=Sof(H4SA)=Sof(H4SB)=Sof(C5S)=Sof(H5SA)=Sof(H5SB)=Sof(H5SC)=FVAR(1)
 Sof(F2A)=Sof(F1A)=Sof(F3A)=Sof(F4A)=1-FVAR(2)
 Sof(F2)=Sof(F1)=Sof(F3)=Sof(F4)=FVAR(2)
5.a Secondary CH2 refined with riding coordinates:
 C7S(H7SA,H7SB), C9S(H9SA,H9SB), C2S(H2SA,H2SB), C4S(H4SA,H4SB), C4SA(H4SC,H4SD)
5.b Aromatic/amide H refined with riding coordinates:
 N1(H1), N2(H2), C7(H7), C9(H9), C6(H6), C10(H10), C18(H18), C15(H15),
 C25(H25), C16(H16), C28(H28), C26(H26), C17(H17), C27(H27)
5.c Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C31(H31A,H31B,H31C), C8S(H8SA,H8SB,H8SC), C1(H1A,H1B,
 H1C), C10S(H10A,H10B,H10C), C3S(H3SA,H3SB,H3SC), C5S(H5SA,H5SB,H5SC),
 C5SA(H5SD,H5SE,H5SF)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.53700(5) 0.72356(3) 0.28365(2) 0.02277(8) Uani 1 1 d . . . . .
S2 S 0.35175(5) 1.11998(4) 0.50655(2) 0.02990(10) Uani 1 1 d . . . . .
N1 N 0.49703(15) 1.10803(10) 0.21174(5) 0.0163(2) Uani 1 1 d . . . . .
H1 H 0.491311 1.069855 0.172412 0.020 Uiso 1 1 calc R . . . .
N2 N 0.52252(15) 1.24966(10) 0.28830(5) 0.0157(2) Uani 1 1 d . . . . .
H2 H 0.537052 1.321160 0.308347 0.019 Uiso 1 1 calc R . . . .
C8 C 0.56306(17) 1.31231(11) 0.17312(6) 0.0152(2) Uani 1 1 d . . . . .
O2 O 0.78068(17) 1.53038(10) -0.02011(6) 0.0306(3) Uani 1 1 d . . . . .
O6S O 0.44782(15) 0.97568(10) 0.09239(5) 0.0250(2) Uani 1 1 d . . . . .
C20 C 0.59029(18) 0.87806(12) 0.29367(7) 0.0184(2) Uani 1 1 d . . . . .
C13 C 0.45897(18) 0.92580(12) 0.27307(6) 0.0170(2) Uani 1 1 d . . . . .
C5 C 0.65623(18) 1.47825(12) 0.07999(7) 0.0178(2) Uani 1 1 d . . . . .
C7 C 0.6217(2) 1.27861(12) 0.11244(7) 0.0209(3) Uani 1 1 d . . . . .
H7 H 0.630394 1.198894 0.102889 0.025 Uiso 1 1 calc R . . . .
C9 C 0.54785(19) 1.42900(12) 0.18656(7) 0.0199(3) Uani 1 1 d . . . . .
H9 H 0.505829 1.451884 0.227504 0.024 Uiso 1 1 calc R . . . .
C12 C 0.47795(18) 1.05491(12) 0.27119(6) 0.0165(2) Uani 1 1 d . . . . .
C11 C 0.52542(17) 1.22587(11) 0.22303(6) 0.0154(2) Uani 1 1 d . . . . .
C3 C 0.7142(2) 1.57145(13) 0.03304(7) 0.0223(3) Uani 1 1 d . . . . .
C14 C 0.30903(18) 0.83810(12) 0.24742(7) 0.0185(2) Uani 1 1 d . . . . .
C6 C 0.6675(2) 1.36146(13) 0.06606(7) 0.0214(3) Uani 1 1 d . . . . .
H6 H 0.706590 1.338237 0.024610 0.026 Uiso 1 1 calc R . . . .
C19 C 0.33462(19) 0.72224(13) 0.24961(7) 0.0209(3) Uani 1 1 d . . . . .
C22 C 0.49309(17) 1.14455(12) 0.31983(6) 0.0164(2) Uani 1 1 d . . . . .
C10 C 0.5943(2) 1.51153(12) 0.13998(7) 0.0216(3) Uani 1 1 d . . . . .
H10 H 0.583715 1.590958 0.149042 0.026 Uiso 1 1 calc R . . . .
C23 C 0.48049(18) 1.14369(12) 0.39200(6) 0.0179(2) Uani 1 1 d . . . . .
C24 C 0.62338(19) 1.18399(13) 0.43944(7) 0.0202(3) Uani 1 1 d . . . . .
C29 C 0.5711(2) 1.17530(14) 0.50498(7) 0.0246(3) Uani 1 1 d . . . . .
O4 O 0.7037(2) 1.67308(11) 0.04256(7) 0.0463(4) Uani 1 1 d . . . . .
C21 C 0.7665(2) 0.93949(14) 0.31962(8) 0.0258(3) Uani 1 1 d . . . . .
H21A H 0.766343 0.956670 0.367650 0.039 Uiso 1 1 calc GR . . . .
H21B H 0.803088 1.013955 0.298318 0.039 Uiso 1 1 calc GR . . . .
H21C H 0.845810 0.888202 0.309934 0.039 Uiso 1 1 calc GR . . . .
C18 C 0.2097(2) 0.62255(14) 0.22533(9) 0.0298(3) Uani 1 1 d . . . . .
H18 H 0.229087 0.544839 0.226737 0.036 Uiso 1 1 calc R . . . .
C15 C 0.1518(2) 0.85426(14) 0.22182(8) 0.0243(3) Uani 1 1 d . . . . .
H15 H 0.130803 0.931593 0.220790 0.029 Uiso 1 1 calc R . . . .
C25 C 0.7983(2) 1.22384(14) 0.42878(8) 0.0259(3) Uani 1 1 d . . . . .
H25 H 0.836531 1.231426 0.385065 0.031 Uiso 1 1 calc R . . . .
C30 C 0.32820(19) 1.10611(14) 0.42075(7) 0.0224(3) Uani 1 1 d . . . . .
C16 C 0.0274(2) 0.75491(16) 0.19798(10) 0.0341(4) Uani 1 1 d . . . . .
H16 H -0.079650 0.764711 0.180551 0.041 Uiso 1 1 calc R . . . .
C31 C 0.1549(2) 1.05689(17) 0.38797(8) 0.0314(3) Uani 1 1 d . . . . .
H31A H 0.139973 0.971433 0.377083 0.047 Uiso 1 1 calc GR . . . .
H31B H 0.143867 1.096462 0.347247 0.047 Uiso 1 1 calc GR . . . .
H31C H 0.066986 1.070472 0.418047 0.047 Uiso 1 1 calc GR . . . .
C28 C 0.6883(3) 1.20467(17) 0.55953(8) 0.0338(4) Uani 1 1 d . . . . .
H28 H 0.651053 1.199068 0.603465 0.041 Uiso 1 1 calc R . . . .
C8S C 0.7180(3) 0.92914(19) 0.11581(9) 0.0409(5) Uani 1 1 d . . . . .
H8SA H 0.771564 1.003359 0.096832 0.061 Uiso 1 1 calc GR . . . .
H8SB H 0.786186 0.870081 0.106777 0.061 Uiso 1 1 calc GR . . . .
H8SC H 0.712337 0.943777 0.163801 0.061 Uiso 1 1 calc GR . . . .
C26 C 0.9142(2) 1.25194(17) 0.48292(9) 0.0347(4) Uani 1 1 d . . . . .
H26 H 1.032789 1.278419 0.476025 0.042 Uiso 1 1 calc R . . . .
C17 C 0.0573(2) 0.64061(16) 0.19923(11) 0.0364(4) Uani 1 1 d . . . . .
H17 H -0.029036 0.574287 0.181792 0.044 Uiso 1 1 calc R . . . .
C7S C 0.5406(3) 0.88362(15) 0.08525(9) 0.0340(4) Uani 1 1 d . . . . .
H7SA H 0.546128 0.859528 0.037707 0.041 Uiso 1 1 calc R . . . .
H7SB H 0.481461 0.813312 0.107456 0.041 Uiso 1 1 calc R . . . .
C1 C 0.8459(3) 1.61701(17) -0.06690(9) 0.0361(4) Uani 1 1 d . . . . .
H1A H 0.898147 1.579201 -0.102844 0.054 Uiso 1 1 calc GR . . . .
H1B H 0.932052 1.682440 -0.044205 0.054 Uiso 1 1 calc GR . . . .
H1C H 0.751434 1.647943 -0.085266 0.054 Uiso 1 1 calc GR . . . .
C9S C 0.2802(2) 0.94410(18) 0.06048(8) 0.0357(4) Uani 1 1 d . . . . .
H9SA H 0.211231 0.873233 0.079475 0.043 Uiso 1 1 calc R . . . .
H9SB H 0.288356 0.924767 0.012523 0.043 Uiso 1 1 calc R . . . .
C10S C 0.1959(3) 1.0461(2) 0.07046(10) 0.0456(5) Uani 1 1 d . . . . .
H10A H 0.080238 1.024604 0.049299 0.068 Uiso 1 1 calc GR . . . .
H10B H 0.263281 1.115363 0.050620 0.068 Uiso 1 1 calc GR . . . .
H10C H 0.188921 1.065119 0.118005 0.068 Uiso 1 1 calc GR . . . .
F2 F 0.9035(2) 1.2280(2) 0.26873(9) 0.0499(5) Uani 0.893(3) 1 d D . P A 1
F1 F 1.1109(2) 1.13716(17) 0.23467(7) 0.0462(4) Uani 0.893(3) 1 d D . P A 1
F3 F 1.1505(3) 1.33298(14) 0.22625(9) 0.0657(6) Uani 0.893(3) 1 d D . P A 1
F4 F 0.9514(2) 1.20702(18) 0.15912(8) 0.0510(4) Uani 0.893(3) 1 d D . P A 1
B1 B 1.0280(2) 1.22820(16) 0.22302(9) 0.0266(3) Uani 1 1 d D . . . .
C27 C 0.8594(3) 1.24197(18) 0.54774(9) 0.0376(4) Uani 1 1 d . . . . .
H27 H 0.941555 1.261222 0.584044 0.045 Uiso 1 1 calc R . . . .
C2S C 0.7287(3) 1.51866(19) 0.38940(12) 0.0480(6) Uani 1 1 d D U . . .
H2SA H 0.760567 1.475429 0.426691 0.058 Uiso 1 1 calc R . . . .
H2SB H 0.733561 1.601637 0.406059 0.058 Uiso 1 1 calc R . . . .
C3S C 0.8502(3) 1.5167(2) 0.33529(16) 0.0573(7) Uani 1 1 d D U . . .
H3SA H 0.814800 1.556473 0.297780 0.086 Uiso 1 1 calc GR . . . .
H3SB H 0.849622 1.434183 0.320867 0.086 Uiso 1 1 calc GR . . . .
H3SC H 0.966046 1.557996 0.351755 0.086 Uiso 1 1 calc GR . . . .
O1S O 0.55891(16) 1.46320(11) 0.36343(6) 0.0290(2) Uani 1 1 d D U . . .
C4S C 0.4368(3) 1.4712(2) 0.41160(10) 0.0355(5) Uani 0.855(5) 1 d D U P B 1
H4SA H 0.452209 1.554461 0.429816 0.043 Uiso 0.855(5) 1 calc R . P B 1
H4SB H 0.451806 1.421837 0.448503 0.043 Uiso 0.855(5) 1 calc R . P B 1
C5S C 0.2625(3) 1.4281(3) 0.37878(13) 0.0460(7) Uani 0.855(5) 1 d D U P B 1
H5SA H 0.250309 1.475752 0.341414 0.069 Uiso 0.855(5) 1 calc GR . P B 1
H5SB H 0.175950 1.435691 0.410740 0.069 Uiso 0.855(5) 1 calc GR . P B 1
H5SC H 0.246745 1.344628 0.362606 0.069 Uiso 0.855(5) 1 calc GR . P B 1
C4SA C 0.3877(18) 1.4222(13) 0.4008(7) 0.0355(5) Uani 0.145(5) 1 d D U P B 2
H4SC H 0.306964 1.359621 0.372589 0.043 Uiso 0.145(5) 1 calc R . P B 2
H4SD H 0.414007 1.387524 0.442270 0.043 Uiso 0.145(5) 1 calc R . P B 2
C5SA C 0.306(2) 1.5214(14) 0.4168(7) 0.046(4) Uani 0.145(5) 1 d D U P B 2
H5SD H 0.239647 1.535368 0.377666 0.070 Uiso 0.145(5) 1 calc GR . P B 2
H5SE H 0.393678 1.593220 0.430503 0.070 Uiso 0.145(5) 1 calc GR . P B 2
H5SF H 0.228568 1.501661 0.453034 0.070 Uiso 0.145(5) 1 calc GR . P B 2
F2A F 0.948(2) 1.227(2) 0.2842(8) 0.0499(5) Uani 0.107(3) 1 d D . P A 2
F1A F 1.1605(18) 1.1937(14) 0.2348(7) 0.0462(4) Uani 0.107(3) 1 d D . P A 2
F3A F 1.039(2) 1.3500(10) 0.2150(8) 0.0657(6) Uani 0.107(3) 1 d D . P A 2
F4A F 0.917(2) 1.1699(15) 0.1737(7) 0.0510(4) Uani 0.107(3) 1 d D . P 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 C20 1.7415(14) . ?
S1 C19 1.7376(16) . ?
S2 C29 1.7339(17) . ?
S2 C30 1.7339(15) . ?
N1 H1 0.8800 . ?
N1 C12 1.3852(16) . ?
N1 C11 1.3362(17) . ?
N2 H2 0.8800 . ?
N2 C11 1.3345(16) . ?
N2 C22 1.3893(16) . ?
C8 C7 1.3944(18) . ?
C8 C9 1.3954(18) . ?
C8 C11 1.4606(17) . ?
O2 C3 1.3255(18) . ?
O2 C1 1.4495(19) . ?
O6S C7S 1.435(2) . ?
O6S C9S 1.431(2) . ?
C20 C13 1.3606(19) . ?
C20 C21 1.492(2) . ?
C13 C12 1.4728(18) . ?
C13 C14 1.444(2) . ?
C5 C3 1.4919(19) . ?
C5 C6 1.3882(19) . ?
C5 C10 1.3925(19) . ?
C7 H7 0.9500 . ?
C7 C6 1.3863(19) . ?
C9 H9 0.9500 . ?
C9 C10 1.3874(19) . ?
C12 C22 1.3657(18) . ?
C3 O4 1.2034(19) . ?
C14 C19 1.4066(19) . ?
C14 C15 1.403(2) . ?
C6 H6 0.9500 . ?
C19 C18 1.397(2) . ?
C22 C23 1.4690(18) . ?
C10 H10 0.9500 . ?
C23 C24 1.441(2) . ?
C23 C30 1.365(2) . ?
C24 C29 1.4089(19) . ?
C24 C25 1.404(2) . ?
C29 C28 1.398(2) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C18 H18 0.9500 . ?
C18 C17 1.379(3) . ?
C15 H15 0.9500 . ?
C15 C16 1.390(2) . ?
C25 H25 0.9500 . ?
C25 C26 1.385(2) . ?
C30 C31 1.492(2) . ?
C16 H16 0.9500 . ?
C16 C17 1.400(3) . ?
C31 H31A 0.9800 . ?
C31 H31B 0.9800 . ?
C31 H31C 0.9800 . ?
C28 H28 0.9500 . ?
C28 C27 1.377(3) . ?
C8S H8SA 0.9800 . ?
C8S H8SB 0.9800 . ?
C8S H8SC 0.9800 . ?
C8S C7S 1.498(3) . ?
C26 H26 0.9500 . ?
C26 C27 1.402(3) . ?
C17 H17 0.9500 . ?
C7S H7SA 0.9900 . ?
C7S H7SB 0.9900 . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C9S H9SA 0.9900 . ?
C9S H9SB 0.9900 . ?
C9S C10S 1.494(3) . ?
C10S H10A 0.9800 . ?
C10S H10B 0.9800 . ?
C10S H10C 0.9800 . ?
F2 B1 1.385(2) . ?
F1 B1 1.396(2) . ?
F3 B1 1.376(2) . ?
F4 B1 1.395(2) . ?
B1 F2A 1.415(13) . ?
B1 F1A 1.238(11) . ?
B1 F3A 1.415(12) . ?
B1 F4A 1.350(12) . ?
C27 H27 0.9500 . ?
C2S H2SA 0.9900 . ?
C2S H2SB 0.9900 . ?
C2S C3S 1.495(4) . ?
C2S O1S 1.433(2) . ?
C3S H3SA 0.9800 . ?
C3S H3SB 0.9800 . ?
C3S H3SC 0.9800 . ?
O1S C4S 1.420(2) . ?
O1S C4SA 1.584(12) . ?
C4S H4SA 0.9900 . ?
C4S H4SB 0.9900 . ?
C4S C5S 1.491(4) . ?
C5S H5SA 0.9800 . ?
C5S H5SB 0.9800 . ?
C5S H5SC 0.9800 . ?
C4SA H4SC 0.9900 . ?
C4SA H4SD 0.9900 . ?
C4SA C5SA 1.474(14) . ?
C5SA H5SD 0.9800 . ?
C5SA H5SE 0.9800 . ?
C5SA H5SF 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
C19 S1 C20 91.94(7) . . ?
C29 S2 C30 92.09(7) . . ?
C12 N1 H1 125.1 . . ?
C11 N1 H1 125.1 . . ?
C11 N1 C12 109.85(11) . . ?
C11 N2 H2 125.1 . . ?
C11 N2 C22 109.75(11) . . ?
C22 N2 H2 125.1 . . ?
C7 C8 C9 119.86(12) . . ?
C7 C8 C11 119.32(12) . . ?
C9 C8 C11 120.77(12) . . ?
C3 O2 C1 115.74(13) . . ?
C9S O6S C7S 113.46(14) . . ?
C13 C20 S1 111.87(11) . . ?
C13 C20 C21 129.10(13) . . ?
C21 C20 S1 118.97(11) . . ?
C20 C13 C12 122.01(13) . . ?
C20 C13 C14 113.51(12) . . ?
C14 C13 C12 124.18(12) . . ?
C6 C5 C3 121.71(12) . . ?
C6 C5 C10 119.89(12) . . ?
C10 C5 C3 118.37(12) . . ?
C8 C7 H7 120.0 . . ?
C6 C7 C8 119.99(12) . . ?
C6 C7 H7 120.0 . . ?
C8 C9 H9 120.1 . . ?
C10 C9 C8 119.83(12) . . ?
C10 C9 H9 120.1 . . ?
N1 C12 C13 120.75(11) . . ?
C22 C12 N1 106.53(11) . . ?
C22 C12 C13 132.57(12) . . ?
N1 C11 C8 125.84(11) . . ?
N2 C11 N1 107.43(11) . . ?
N2 C11 C8 126.63(12) . . ?
O2 C3 C5 112.57(12) . . ?
O4 C3 O2 123.56(14) . . ?
O4 C3 C5 123.86(14) . . ?
C19 C14 C13 111.41(12) . . ?
C15 C14 C13 129.35(13) . . ?
C15 C14 C19 119.23(13) . . ?
C5 C6 H6 119.9 . . ?
C7 C6 C5 120.21(13) . . ?
C7 C6 H6 119.9 . . ?
C14 C19 S1 111.25(11) . . ?
C18 C19 S1 126.77(12) . . ?
C18 C19 C14 121.96(14) . . ?
N2 C22 C23 121.67(12) . . ?
C12 C22 N2 106.43(11) . . ?
C12 C22 C23 131.88(12) . . ?
C5 C10 H10 119.9 . . ?
C9 C10 C5 120.19(13) . . ?
C9 C10 H10 119.9 . . ?
C24 C23 C22 124.42(12) . . ?
C30 C23 C22 122.33(13) . . ?
C30 C23 C24 113.23(12) . . ?
C29 C24 C23 111.48(13) . . ?
C25 C24 C23 129.56(13) . . ?
C25 C24 C29 118.91(14) . . ?
C24 C29 S2 111.18(11) . . ?
C28 C29 S2 126.87(12) . . ?
C28 C29 C24 121.91(15) . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C19 C18 H18 121.1 . . ?
C17 C18 C19 117.84(15) . . ?
C17 C18 H18 121.1 . . ?
C14 C15 H15 120.7 . . ?
C16 C15 C14 118.69(14) . . ?
C16 C15 H15 120.7 . . ?
C24 C25 H25 120.5 . . ?
C26 C25 C24 119.02(15) . . ?
C26 C25 H25 120.5 . . ?
C23 C30 S2 112.02(11) . . ?
C23 C30 C31 128.54(13) . . ?
C31 C30 S2 119.44(11) . . ?
C15 C16 H16 119.5 . . ?
C15 C16 C17 121.06(16) . . ?
C17 C16 H16 119.5 . . ?
C30 C31 H31A 109.5 . . ?
C30 C31 H31B 109.5 . . ?
C30 C31 H31C 109.5 . . ?
H31A C31 H31B 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C29 C28 H28 121.0 . . ?
C27 C28 C29 118.07(15) . . ?
C27 C28 H28 121.0 . . ?
H8SA C8S H8SB 109.5 . . ?
H8SA C8S H8SC 109.5 . . ?
H8SB C8S H8SC 109.5 . . ?
C7S C8S H8SA 109.5 . . ?
C7S C8S H8SB 109.5 . . ?
C7S C8S H8SC 109.5 . . ?
C25 C26 H26 119.4 . . ?
C25 C26 C27 121.13(17) . . ?
C27 C26 H26 119.4 . . ?
C18 C17 C16 121.19(16) . . ?
C18 C17 H17 119.4 . . ?
C16 C17 H17 119.4 . . ?
O6S C7S C8S 108.98(14) . . ?
O6S C7S H7SA 109.9 . . ?
O6S C7S H7SB 109.9 . . ?
C8S C7S H7SA 109.9 . . ?
C8S C7S H7SB 109.9 . . ?
H7SA C7S H7SB 108.3 . . ?
O2 C1 H1A 109.5 . . ?
O2 C1 H1B 109.5 . . ?
O2 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O6S C9S H9SA 109.9 . . ?
O6S C9S H9SB 109.9 . . ?
O6S C9S C10S 109.02(15) . . ?
H9SA C9S H9SB 108.3 . . ?
C10S C9S H9SA 109.9 . . ?
C10S C9S H9SB 109.9 . . ?
C9S C10S H10A 109.5 . . ?
C9S C10S H10B 109.5 . . ?
C9S C10S H10C 109.5 . . ?
H10A C10S H10B 109.5 . . ?
H10A C10S H10C 109.5 . . ?
H10B C10S H10C 109.5 . . ?
F2 B1 F1 109.04(16) . . ?
F2 B1 F4 109.66(17) . . ?
F3 B1 F2 113.27(19) . . ?
F3 B1 F1 107.70(18) . . ?
F3 B1 F4 108.67(16) . . ?
F4 B1 F1 108.37(16) . . ?
F2A B1 F3A 95.3(11) . . ?
F1A B1 F2A 104.8(9) . . ?
F1A B1 F3A 119.5(10) . . ?
F1A B1 F4A 118.7(10) . . ?
F4A B1 F2A 111.1(11) . . ?
F4A B1 F3A 104.9(9) . . ?
C28 C27 C26 120.95(16) . . ?
C28 C27 H27 119.5 . . ?
C26 C27 H27 119.5 . . ?
H2SA C2S H2SB 108.3 . . ?
C3S C2S H2SA 110.0 . . ?
C3S C2S H2SB 110.0 . . ?
O1S C2S H2SA 110.0 . . ?
O1S C2S H2SB 110.0 . . ?
O1S C2S C3S 108.62(17) . . ?
C2S C3S H3SA 109.5 . . ?
C2S C3S H3SB 109.5 . . ?
C2S C3S H3SC 109.5 . . ?
H3SA C3S H3SB 109.5 . . ?
H3SA C3S H3SC 109.5 . . ?
H3SB C3S H3SC 109.5 . . ?
C2S O1S C4SA 130.0(6) . . ?
C4S O1S C2S 110.74(17) . . ?
O1S C4S H4SA 110.1 . . ?
O1S C4S H4SB 110.1 . . ?
O1S C4S C5S 108.03(18) . . ?
H4SA C4S H4SB 108.4 . . ?
C5S C4S H4SA 110.1 . . ?
C5S C4S H4SB 110.1 . . ?
C4S C5S H5SA 109.5 . . ?
C4S C5S H5SB 109.5 . . ?
C4S C5S H5SC 109.5 . . ?
H5SA C5S H5SB 109.5 . . ?
H5SA C5S H5SC 109.5 . . ?
H5SB C5S H5SC 109.5 . . ?
O1S C4SA H4SC 109.2 . . ?
O1S C4SA H4SD 109.2 . . ?
H4SC C4SA H4SD 107.9 . . ?
C5SA C4SA O1S 112.0(11) . . ?
C5SA C4SA H4SC 109.2 . . ?
C5SA C4SA H4SD 109.2 . . ?
C4SA C5SA H5SD 109.5 . . ?
C4SA C5SA H5SE 109.5 . . ?
C4SA C5SA H5SF 109.5 . . ?
H5SD C5SA H5SE 109.5 . . ?
H5SD C5SA H5SF 109.5 . . ?
H5SE C5SA H5SF 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
S1 C20 C13 C12 -174.64(10) . . . . ?
S1 C20 C13 C14 -0.63(15) . . . . ?
S1 C19 C18 C17 -179.04(14) . . . . ?
S2 C29 C28 C27 176.82(15) . . . . ?
N1 C12 C22 N2 -0.52(15) . . . . ?
N1 C12 C22 C23 178.27(14) . . . . ?
N2 C22 C23 C24 -71.65(19) . . . . ?
N2 C22 C23 C30 106.90(17) . . . . ?
C8 C7 C6 C5 0.5(2) . . . . ?
C8 C9 C10 C5 -0.1(2) . . . . ?
C20 S1 C19 C14 -1.09(11) . . . . ?
C20 S1 C19 C18 177.50(15) . . . . ?
C20 C13 C12 N1 103.28(16) . . . . ?
C20 C13 C12 C22 -71.5(2) . . . . ?
C20 C13 C14 C19 -0.19(17) . . . . ?
C20 C13 C14 C15 -179.67(14) . . . . ?
C13 C12 C22 N2 174.81(14) . . . . ?
C13 C12 C22 C23 -6.4(3) . . . . ?
C13 C14 C19 S1 0.92(15) . . . . ?
C13 C14 C19 C18 -177.74(14) . . . . ?
C13 C14 C15 C16 178.01(15) . . . . ?
C7 C8 C9 C10 -1.2(2) . . . . ?
C7 C8 C11 N1 -19.1(2) . . . . ?
C7 C8 C11 N2 156.85(14) . . . . ?
C9 C8 C7 C6 1.0(2) . . . . ?
C9 C8 C11 N1 163.62(14) . . . . ?
C9 C8 C11 N2 -20.4(2) . . . . ?
C12 N1 C11 N2 -0.90(15) . . . . ?
C12 N1 C11 C8 175.69(13) . . . . ?
C12 C13 C14 C19 173.66(12) . . . . ?
C12 C13 C14 C15 -5.8(2) . . . . ?
C12 C22 C23 C24 109.71(18) . . . . ?
C12 C22 C23 C30 -71.7(2) . . . . ?
C11 N1 C12 C13 -175.11(12) . . . . ?
C11 N1 C12 C22 0.89(16) . . . . ?
C11 N2 C22 C12 -0.01(16) . . . . ?
C11 N2 C22 C23 -178.95(12) . . . . ?
C11 C8 C7 C6 -176.26(14) . . . . ?
C11 C8 C9 C10 176.06(14) . . . . ?
C3 C5 C6 C7 176.24(14) . . . . ?
C3 C5 C10 C9 -176.47(14) . . . . ?
C14 C13 C12 N1 -70.07(18) . . . . ?
C14 C13 C12 C22 115.13(18) . . . . ?
C14 C19 C18 C17 -0.6(3) . . . . ?
C14 C15 C16 C17 -0.1(3) . . . . ?
C6 C5 C3 O2 -2.3(2) . . . . ?
C6 C5 C3 O4 178.49(17) . . . . ?
C6 C5 C10 C9 1.7(2) . . . . ?
C19 S1 C20 C13 0.99(11) . . . . ?
C19 S1 C20 C21 -176.60(12) . . . . ?
C19 C14 C15 C16 -1.4(2) . . . . ?
C19 C18 C17 C16 -0.9(3) . . . . ?
C22 N2 C11 N1 0.56(15) . . . . ?
C22 N2 C11 C8 -175.99(13) . . . . ?
C22 C23 C24 C29 178.44(13) . . . . ?
C22 C23 C24 C25 -4.3(2) . . . . ?
C22 C23 C30 S2 -177.90(11) . . . . ?
C22 C23 C30 C31 2.4(3) . . . . ?
C10 C5 C3 O2 175.82(14) . . . . ?
C10 C5 C3 O4 -3.4(2) . . . . ?
C10 C5 C6 C7 -1.8(2) . . . . ?
C23 C24 C29 S2 -0.45(17) . . . . ?
C23 C24 C29 C28 177.32(15) . . . . ?
C23 C24 C25 C26 -176.32(16) . . . . ?
C24 C23 C30 S2 0.80(17) . . . . ?
C24 C23 C30 C31 -178.87(16) . . . . ?
C24 C29 C28 C27 -0.6(3) . . . . ?
C24 C25 C26 C27 -0.4(3) . . . . ?
C29 S2 C30 C23 -0.90(13) . . . . ?
C29 S2 C30 C31 178.81(14) . . . . ?
C29 C24 C25 C26 0.8(2) . . . . ?
C29 C28 C27 C26 1.0(3) . . . . ?
C21 C20 C13 C12 2.6(2) . . . . ?
C21 C20 C13 C14 176.65(14) . . . . ?
C15 C14 C19 S1 -179.54(11) . . . . ?
C15 C14 C19 C18 1.8(2) . . . . ?
C15 C16 C17 C18 1.3(3) . . . . ?
C25 C24 C29 S2 -178.07(12) . . . . ?
C25 C24 C29 C28 -0.3(2) . . . . ?
C25 C26 C27 C28 -0.5(3) . . . . ?
C30 S2 C29 C24 0.76(13) . . . . ?
C30 S2 C29 C28 -176.88(17) . . . . ?
C30 C23 C24 C29 -0.22(18) . . . . ?
C30 C23 C24 C25 177.08(16) . . . . ?
C7S O6S C9S C10S -179.52(15) . . . . ?
C1 O2 C3 C5 -177.77(14) . . . . ?
C1 O2 C3 O4 1.5(3) . . . . ?
C9S O6S C7S C8S 175.70(14) . . . . ?
C2S O1S C4S C5S 171.91(19) . . . . ?
C2S O1S C4SA C5SA 82.0(12) . . . . ?
C3S C2S O1S C4S -175.44(18) . . . . ?
C3S C2S O1S C4SA 168.6(7) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetonitrile diethyl ether'
####################################################################### 
# 
# 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_mo_gb033_0m
_database_code_depnum_ccdc_archive 'CCDC 1877447'
loop_
_audit_author_name
_audit_author_address
'Giorgio Baggi'
;University of Windsor
Canada
;
_audit_update_record             
;
2018-11-06 deposited with the CCDC.	2019-04-09 downloaded from the CCDC.
;
_audit_creation_date             2018-10-16
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3

# start Validation Reply Form
_vrf_PLAT411_mo_gb033_0m         
;
PROBLEM: Short Inter H...H Contact H30 ..H23A . 1.41 Ang.
RESPONSE: Due to disorder of the benzothiophene fragment.
;
_vrf_PLAT413_mo_gb033_0m         
;
PROBLEM: Short Inter XH3 .. XHn H2SC ..H24A . 1.89 Ang.
RESPONSE: Due to disorder of the benzothiophene fragment.
;
_vrf_PLAT910_mo_gb033_0m         
;
PROBLEM: Missing # of FCF Reflection(s) Below Theta(Min). 14 Note
RESPONSE: The missing reflections were masked by the beamstop, hence they were not measured.
;
# end Validation Reply Form

_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C27 H21 N2 S2, C24 H32 O8, B F4, C4 H10 O'
_chemical_formula_sum            'C55 H63 B F4 N2 O9 S2'
_chemical_formula_weight         1047.00
_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'
B B 0.0013 0.0007 '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/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   13.2818(6)
_cell_length_b                   19.8213(8)
_cell_length_c                   20.1065(9)
_cell_angle_alpha                90
_cell_angle_beta                 93.248(2)
_cell_angle_gamma                90
_cell_volume                     5284.8(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9987
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      28.22
_cell_measurement_theta_min      3.072
_shelx_estimated_absorpt_T_max   0.958
_shelx_estimated_absorpt_T_min   0.940
_exptl_absorpt_coefficient_mu    0.173
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6937
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0605 before and 0.0562 after correction. The Ratio of minimum to maximum transmission is 0.9303. The λ/2 correction factor is 0.00150.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.316
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Block
_exptl_crystal_F_000             2208
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.252
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0548
_diffrn_reflns_av_unetI/netI     0.0224
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            168940
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.333
_diffrn_reflns_theta_min         2.808
_diffrn_ambient_temperature      173.21
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_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_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                10120
_reflns_number_total             13131
_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, 2015)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.790
_refine_diff_density_min         -0.665
_refine_diff_density_rms         0.075
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.160
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     780
_refine_ls_number_reflns         13131
_refine_ls_number_restraints     363
_refine_ls_R_factor_all          0.1100
_refine_ls_R_factor_gt           0.0836
_refine_ls_restrained_S_all      1.149
_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)+(0.0618P)²+12.3194P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2057
_refine_ls_wR_factor_ref         0.2252
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained planarity
 C27A, C26A, C19A, C20A, C21A, C22A, C23A, C24A, C25A, S2A
 with sigma of 0.1
3. Uiso/Uaniso restraints and constraints
S2 \\sim C19 \\sim C26 \\sim C20 \\sim C21 \\sim C27 \\sim C25 \\sim C24 \\sim
C23 \\sim C22 \\sim S2A \\sim C19A \\sim C26A \\sim C20A \\sim C21A \\sim C27A
\\sim C25A \\sim C24A \\sim C23A \\sim C22A: within 2A with sigma of 0.04 and
sigma for terminal atoms of 0.08
Uanis(C25) = Uanis(C25A)
Uanis(O8) = Uanis(O8A)
Uanis(F3) = Uanis(F3A)
Uanis(F2) = Uanis(F2A)
Uanis(F4) = Uanis(F4A)
4. Rigid body (RIGU) restrains
 O1S, C2S, C1S, C3S, C4S
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Same fragment restrains
{S2A, C19A, C26A, C20A, C21A, C27A, C25A, C24A, C23A, C22A} sigma for 1-2:
0.02, 1-3: 0.02
as
{S2, C19, C26, C20, C21, C27, C25, C24, C23, C22}
{F4A, F3A, F2A, F1, B1} sigma for 1-2: 0.02, 1-3: 0.02
as
{F4, F3, F2, F1, B1}
6. Others
 Sof(H48C)=Sof(H48D)=Sof(H51C)=Sof(H51D)=Sof(O8A)=Sof(C50A)=Sof(H50C)=
 Sof(H50D)=Sof(C49A)=Sof(H49C)=Sof(H49D)=1-FVAR(1)
 Sof(H48A)=Sof(H48B)=Sof(H51A)=Sof(H51B)=Sof(O8)=Sof(C50)=Sof(H50A)=Sof(H50B)=
 Sof(C49)=Sof(H49A)=Sof(H49B)=FVAR(1)
 Sof(S2A)=Sof(C19A)=Sof(C26A)=Sof(C20A)=Sof(C21A)=Sof(H21A)=Sof(C27A)=
 Sof(H27D)=Sof(H27E)=Sof(H27F)=Sof(C25A)=Sof(C24A)=Sof(H24A)=Sof(C23A)=
 Sof(H23A)=Sof(C22A)=Sof(H22A)=1-FVAR(2)
 Sof(S2)=Sof(C19)=Sof(C26)=Sof(C20)=Sof(C21)=Sof(H21)=Sof(C27)=Sof(H27A)=
 Sof(H27B)=Sof(H27C)=Sof(C25)=Sof(C24)=Sof(H24)=Sof(C23)=Sof(H23)=Sof(C22)=
 Sof(H22)=FVAR(2)
 Sof(F4A)=Sof(F3A)=Sof(F2A)=1-FVAR(3)
 Sof(F4)=Sof(F3)=Sof(F2)=FVAR(3)
7.a Secondary CH2 refined with riding coordinates:
 C36(H36A,H36B), C38(H38A,H38B), C47(H47A,H47B), C39(H39A,H39B), C48(H48A,
 H48B), C48(H48C,H48D), C37(H37A,H37B), C34(H34A,H34B), C51(H51A,H51B),
 C51(H51C,H51D), C46(H46A,H46B), C35(H35A,H35B), C50(H50A,H50B), C49(H49A,H49B),
  C50A(H50C,H50D), C49A(H49C,H49D), C1S(H1SA,H1SB), C3S(H3SA,H3SB)
7.b Aromatic/amide H refined with riding coordinates:
 N1(H1), N2(H2), C6(H6), C4(H4), C2(H2A), C3(H3), C32(H32), C5(H5), C14(H14),
 C41(H41), C11(H11), C13(H13), C43(H43), C29(H29), C12(H12), C44(H44), C30(H30),
  C42(H42), C31(H31), C21(H21), C24(H24), C23(H23), C22(H22), C21A(H21A),
 C24A(H24A), C23A(H23A), C22A(H22A)
7.c Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C27(H27A,H27B,H27C), C27A(H27D,H27E,H27F), C2S(H2SA,H2SB,
 H2SC), C4S(H4SA,H4SB,H4SC)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_special_details      
;
The structure was solved using Direct Methods (ShelXS). RE = 0.2, Nqual =  -1, Ralpha = 0.086
;
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 0.49554(6) 0.85844(4) 0.17942(4) 0.03220(18) Uani 1 1 d . . . . .
O6 O 0.25848(17) 1.00199(12) 0.02831(12) 0.0346(5) Uani 1 1 d . . . . .
O4 O -0.04242(17) 1.06670(13) 0.17728(11) 0.0359(5) Uani 1 1 d . . . . .
O2 O 0.20826(18) 1.16351(13) 0.36057(11) 0.0382(5) Uani 1 1 d . . . . .
O5 O 0.08316(17) 0.98918(12) 0.08060(12) 0.0370(5) Uani 1 1 d . . . . .
O3 O 0.02117(17) 1.13184(13) 0.29810(12) 0.0388(5) Uani 1 1 d . . . . .
O1 O 0.35197(19) 1.20536(14) 0.28737(12) 0.0432(6) Uani 1 1 d . . . . .
O7 O 0.4000(2) 1.11309(13) 0.04705(12) 0.0431(6) Uani 1 1 d . . . . .
N1 N 0.18885(19) 1.07730(12) 0.23574(12) 0.0262(5) Uani 1 1 d . . . . .
H1 H 0.137754 1.090586 0.258489 0.031 Uiso 1 1 calc R . . . .
N2 N 0.29788(18) 1.07238(12) 0.16099(12) 0.0260(5) Uani 1 1 d . . . . .
H2 H 0.331873 1.082147 0.125934 0.031 Uiso 1 1 calc R . . . .
C16 C 0.3833(2) 0.90166(15) 0.18824(14) 0.0269(6) Uani 1 1 d . . . . .
C8 C 0.3177(2) 1.01829(15) 0.20328(15) 0.0267(6) Uani 1 1 d . . . . .
C17 C 0.2881(2) 0.86267(17) 0.19249(17) 0.0331(7) Uani 1 1 d . . . . .
H17A H 0.289664 0.823163 0.163257 0.050 Uiso 1 1 calc GR . . . .
H17B H 0.230598 0.891312 0.178485 0.050 Uiso 1 1 calc GR . . . .
H17C H 0.281329 0.847855 0.238525 0.050 Uiso 1 1 calc GR . . . .
C7 C 0.2196(2) 1.10749(14) 0.18125(14) 0.0250(6) Uani 1 1 d . . . . .
C18 C 0.2495(2) 1.02169(15) 0.25130(15) 0.0265(6) Uani 1 1 d . . . . .
C6 C 0.1420(2) 1.22008(15) 0.18744(16) 0.0302(6) Uani 1 1 d . . . . .
H6 H 0.152952 1.219072 0.234537 0.036 Uiso 1 1 calc R . . . .
C1 C 0.1737(2) 1.16668(15) 0.14865(15) 0.0261(6) Uani 1 1 d . . . . .
C10 C 0.5034(2) 0.98839(16) 0.19105(15) 0.0295(6) Uani 1 1 d . . . . .
C9 C 0.3983(2) 0.96956(15) 0.19279(15) 0.0267(6) Uani 1 1 d . . . . .
C4 C 0.0790(3) 1.27583(17) 0.08770(18) 0.0388(8) Uani 1 1 d . . . . .
H4 H 0.045190 1.313155 0.066890 0.047 Uiso 1 1 calc R . . . .
C45 C 0.2222(3) 0.93698(17) 0.03338(16) 0.0340(7) Uani 1 1 d . . . . .
C2 C 0.1589(2) 1.16840(17) 0.07962(16) 0.0321(7) Uani 1 1 d . . . . .
H2A H 0.180926 1.131907 0.053477 0.039 Uiso 1 1 calc R . . . .
C3 C 0.1118(3) 1.22372(18) 0.04916(17) 0.0375(7) Uani 1 1 d . . . . .
H3 H 0.102212 1.225628 0.002015 0.045 Uiso 1 1 calc R . . . .
C36 C -0.0801(3) 1.1363(2) 0.2696(2) 0.0463(9) Uani 1 1 d . . . . .
H36A H -0.110035 1.180002 0.281748 0.056 Uiso 1 1 calc R . . . .
H36B H -0.121416 1.099725 0.287540 0.056 Uiso 1 1 calc R . . . .
C28 C 0.3824(3) 1.17572(18) 0.34689(17) 0.0370(7) Uani 1 1 d . . . . .
C40 C 0.1267(3) 0.93099(17) 0.05929(16) 0.0350(7) Uani 1 1 d . . . . .
C38 C -0.0593(3) 1.0549(2) 0.10782(17) 0.0404(8) Uani 1 1 d . . . . .
H38A H -0.023076 1.089143 0.082503 0.048 Uiso 1 1 calc R . . . .
H38B H -0.132233 1.058688 0.095162 0.048 Uiso 1 1 calc R . . . .
C47 C 0.3709(3) 1.08246(19) -0.01489(16) 0.0390(8) Uani 1 1 d . . . . .
H47A H 0.425262 1.087787 -0.046162 0.047 Uiso 1 1 calc R . . . .
H47B H 0.309393 1.104643 -0.034612 0.047 Uiso 1 1 calc R . . . .
C32 C 0.3299(3) 1.1199(2) 0.44521(18) 0.0450(9) Uani 1 1 d . . . . .
H32 H 0.278259 1.102949 0.471404 0.054 Uiso 1 1 calc R . . . .
C33 C 0.3048(3) 1.15148(18) 0.38528(16) 0.0358(7) Uani 1 1 d . . . . .
C5 C 0.0945(3) 1.27461(17) 0.15623(18) 0.0368(7) Uani 1 1 d . . . . .
H5 H 0.072420 1.311344 0.182031 0.044 Uiso 1 1 calc R . . . .
C14 C 0.6707(3) 0.9389(2) 0.18465(18) 0.0395(8) Uani 1 1 d . . . . .
H14 H 0.712512 0.900668 0.179178 0.047 Uiso 1 1 calc R . . . .
C39 C -0.0227(3) 0.9859(2) 0.09114(18) 0.0400(8) Uani 1 1 d . . . . .
H39A H -0.034751 0.954430 0.128059 0.048 Uiso 1 1 calc R . . . .
H39B H -0.059912 0.969124 0.050400 0.048 Uiso 1 1 calc R . . . .
C48 C 0.4328(3) 1.18119(19) 0.03842(18) 0.0431(8) Uani 1 1 d . . . . .
H48A H 0.373462 1.210950 0.030392 0.052 Uiso 0.691(7) 1 calc R . P A 1
H48B H 0.474414 1.183992 -0.000795 0.052 Uiso 0.691(7) 1 calc R . P A 1
H48C H 0.413851 1.194380 -0.008112 0.052 Uiso 0.309(7) 1 calc R . P A 2
H48D H 0.507356 1.181379 0.043336 0.052 Uiso 0.309(7) 1 calc R . P A 2
C41 C 0.0817(3) 0.86728(18) 0.06168(18) 0.0431(8) Uani 1 1 d . . . . .
H41 H 0.016560 0.862482 0.078374 0.052 Uiso 1 1 calc R . . . .
C11 C 0.5469(3) 1.05266(19) 0.1991(2) 0.0434(8) Uani 1 1 d . . . . .
H11 H 0.505433 1.091300 0.203436 0.052 Uiso 1 1 calc R . . . .
C37 C -0.0807(3) 1.13040(19) 0.1951(2) 0.0412(8) Uani 1 1 d . . . . .
H37A H -0.150407 1.135740 0.175726 0.049 Uiso 1 1 calc R . . . .
H37B H -0.038710 1.166625 0.177134 0.049 Uiso 1 1 calc R . . . .
C15 C 0.5660(2) 0.93233(17) 0.18406(15) 0.0315(6) Uani 1 1 d . . . . .
C13 C 0.7120(3) 1.0024(2) 0.1934(2) 0.0492(9) Uani 1 1 d . . . . .
H13 H 0.783135 1.007743 0.194422 0.059 Uiso 1 1 calc R . . . .
C34 C 0.1283(3) 1.1367(2) 0.39749(18) 0.0441(9) Uani 1 1 d . . . . .
H34A H 0.133961 1.153716 0.443850 0.053 Uiso 1 1 calc R . . . .
H34B H 0.132308 1.086846 0.398711 0.053 Uiso 1 1 calc R . . . .
C51 C 0.4167(3) 1.2555(2) 0.2614(2) 0.0537(11) Uani 1 1 d . . . . .
H51A H 0.456818 1.275495 0.299411 0.064 Uiso 0.691(7) 1 calc R . P A 1
H51B H 0.373472 1.291749 0.241551 0.064 Uiso 0.691(7) 1 calc R . P A 1
H51C H 0.407119 1.298181 0.285737 0.064 Uiso 0.309(7) 1 calc R . P A 2
H51D H 0.487511 1.241115 0.270618 0.064 Uiso 0.309(7) 1 calc R . P A 2
C43 C 0.2274(4) 0.8170(2) 0.0160(2) 0.0530(10) Uani 1 1 d . . . . .
H43 H 0.261994 0.778069 0.001790 0.064 Uiso 1 1 calc R . . . .
C29 C 0.4819(3) 1.1689(2) 0.3704(2) 0.0469(9) Uani 1 1 d . . . . .
H29 H 0.534123 1.186072 0.344778 0.056 Uiso 1 1 calc R . . . .
C46 C 0.3507(3) 1.00921(19) -0.00409(18) 0.0401(8) Uani 1 1 d . . . . .
H46A H 0.345835 0.985359 -0.047417 0.048 Uiso 1 1 calc R . . . .
H46B H 0.406755 0.989030 0.023720 0.048 Uiso 1 1 calc R . . . .
C12 C 0.6504(3) 1.0591(2) 0.2007(2) 0.0538(11) Uani 1 1 d . . . . .
H12 H 0.680251 1.102345 0.206877 0.065 Uiso 1 1 calc R . . . .
C44 C 0.2725(3) 0.88036(19) 0.0130(2) 0.0456(9) Uani 1 1 d . . . . .
H44 H 0.338069 0.884568 -0.003068 0.055 Uiso 1 1 calc R . . . .
C35 C 0.0305(3) 1.1584(2) 0.36418(19) 0.0454(9) Uani 1 1 d . . . . .
H35A H -0.025989 1.141917 0.389912 0.054 Uiso 1 1 calc R . . . .
H35B H 0.027204 1.208238 0.362630 0.054 Uiso 1 1 calc R . . . .
C30 C 0.5064(3) 1.1374(2) 0.4304(2) 0.0536(10) Uani 1 1 d . . . . .
H30 H 0.575000 1.132839 0.445812 0.064 Uiso 1 1 calc R . . . .
C42 C 0.1326(4) 0.81099(19) 0.0395(2) 0.0538(11) Uani 1 1 d . . . . .
H42 H 0.101474 0.767881 0.040691 0.065 Uiso 1 1 calc R . . . .
C31 C 0.4311(4) 1.1127(2) 0.4675(2) 0.0557(11) Uani 1 1 d . . . . .
H31 H 0.447738 1.090666 0.508645 0.067 Uiso 1 1 calc R . . . .
S2 S 0.27791(9) 0.92263(6) 0.42445(5) 0.0472(3) Uani 0.929(3) 1 d D U P B 1
C19 C 0.2389(3) 0.98158(18) 0.31151(17) 0.0270(7) Uani 0.929(3) 1 d D U P B 1
C26 C 0.3174(3) 0.96587(19) 0.35566(18) 0.0319(7) Uani 0.929(3) 1 d D U P B 1
C20 C 0.1438(3) 0.95691(19) 0.33207(19) 0.0347(8) Uani 0.929(3) 1 d D U P B 1
C21 C 0.0476(3) 0.9605(2) 0.2992(2) 0.0447(10) Uani 0.929(3) 1 d D U P B 1
H21 H 0.038975 0.981306 0.256645 0.054 Uiso 0.929(3) 1 calc R . P B 1
C27 C 0.4260(3) 0.9813(2) 0.35260(19) 0.0386(8) Uani 0.929(3) 1 d D U P B 1
H27A H 0.456971 0.984338 0.397909 0.058 Uiso 0.929(3) 1 calc GR . P B 1
H27B H 0.434085 1.024385 0.329609 0.058 Uiso 0.929(3) 1 calc GR . P B 1
H27C H 0.458819 0.945394 0.328267 0.058 Uiso 0.929(3) 1 calc GR . P B 1
C25 C 0.1552(4) 0.9242(2) 0.3942(2) 0.0458(10) Uani 0.929(3) 1 d D U P B 1
C24 C 0.0709(4) 0.8977(3) 0.4251(3) 0.0769(19) Uani 0.929(3) 1 d D U P B 1
H24 H 0.078155 0.877082 0.467746 0.092 Uiso 0.929(3) 1 calc R . P B 1
C23 C -0.0210(4) 0.9028(4) 0.3922(3) 0.083(2) Uani 0.929(3) 1 d D U P B 1
H23 H -0.078203 0.884890 0.412314 0.100 Uiso 0.929(3) 1 calc R . P B 1
C22 C -0.0342(3) 0.9334(3) 0.3294(3) 0.0647(15) Uani 0.929(3) 1 d D U P B 1
H22 H -0.099431 0.935537 0.307602 0.078 Uiso 0.929(3) 1 calc R . P B 1
O8 O 0.4342(4) 1.2092(7) 0.1539(6) 0.0327(13) Uani 0.691(7) 1 d . . P A 1
C50 C 0.4854(4) 1.2353(3) 0.2126(3) 0.0362(12) Uani 0.691(7) 1 d . . P A 1
H50A H 0.526609 1.274605 0.200671 0.043 Uiso 0.691(7) 1 calc R . P A 1
H50B H 0.531557 1.200394 0.232095 0.043 Uiso 0.691(7) 1 calc R . P A 1
C49 C 0.4936(4) 1.2043(3) 0.0998(2) 0.0355(12) Uani 0.691(7) 1 d . . P A 1
H49A H 0.549098 1.171949 0.110010 0.043 Uiso 0.691(7) 1 calc R . P A 1
H49B H 0.523895 1.248857 0.091102 0.043 Uiso 0.691(7) 1 calc R . P A 1
S2A S 0.0947(16) 0.9102(12) 0.3880(12) 0.085(6) Uani 0.071(3) 1 d D U P B 2
C19A C 0.197(2) 0.9783(19) 0.3064(13) 0.033(9) Uani 0.071(3) 1 d D U P B 2
C26A C 0.103(2) 0.9521(18) 0.3130(14) 0.046(8) Uani 0.071(3) 1 d D U P B 2
C20A C 0.264(2) 0.968(2) 0.3639(15) 0.042(7) Uani 0.071(3) 1 d D U P B 2
C21A C 0.367(2) 0.984(2) 0.3737(19) 0.051(10) Uani 0.071(3) 1 d D U P B 2
H21A H 0.403006 1.002013 0.338318 0.061 Uiso 0.071(3) 1 calc R . P B 2
C27A C 0.015(3) 0.952(3) 0.2648(19) 0.10(2) Uani 0.071(3) 1 d D U P B 2
H27D H -0.046151 0.960666 0.288404 0.144 Uiso 0.071(3) 1 calc GR . P B 2
H27E H 0.010077 0.908769 0.242110 0.144 Uiso 0.071(3) 1 calc GR . P B 2
H27F H 0.023336 0.988280 0.231896 0.144 Uiso 0.071(3) 1 calc GR . P B 2
C25A C 0.214(2) 0.935(2) 0.4150(13) 0.0458(10) Uani 0.071(3) 1 d D U P B 2
C24A C 0.266(3) 0.918(3) 0.4753(15) 0.072(11) Uani 0.071(3) 1 d D U P B 2
H24A H 0.235312 0.891490 0.508080 0.086 Uiso 0.071(3) 1 calc R . P B 2
C23A C 0.363(3) 0.939(3) 0.4851(19) 0.080(13) Uani 0.071(3) 1 d D U P B 2
H23A H 0.398196 0.930571 0.526754 0.096 Uiso 0.071(3) 1 calc R . P B 2
C22A C 0.414(2) 0.974(3) 0.436(2) 0.079(14) Uani 0.071(3) 1 d D U P B 2
H22A H 0.480144 0.989996 0.445629 0.095 Uiso 0.071(3) 1 calc R . P B 2
O8A O 0.4102(14) 1.2133(17) 0.1500(16) 0.0327(13) Uani 0.309(7) 1 d . . P A 2
C50A C 0.4022(9) 1.2678(6) 0.1950(6) 0.040(3) Uani 0.309(7) 1 d . . P A 2
H50C H 0.451448 1.302701 0.183165 0.048 Uiso 0.309(7) 1 calc R . P A 2
H50D H 0.334172 1.287709 0.187272 0.048 Uiso 0.309(7) 1 calc R . P A 2
C49A C 0.3960(9) 1.2343(6) 0.0822(6) 0.043(3) Uani 0.309(7) 1 d . . P A 2
H49C H 0.433495 1.276737 0.075463 0.052 Uiso 0.309(7) 1 calc R . P A 2
H49D H 0.323576 1.242905 0.071147 0.052 Uiso 0.309(7) 1 calc R . P A 2
F4 F 0.7571(4) 0.7096(2) 0.0783(3) 0.1222(18) Uani 0.909(5) 1 d D . P C 1
F3 F 0.7959(3) 0.7165(3) 0.1853(3) 0.124(2) Uani 0.909(5) 1 d D . P C 1
F2 F 0.6715(3) 0.78156(18) 0.1398(3) 0.0963(16) Uani 0.909(5) 1 d D . P C 1
F1 F 0.8314(3) 0.8031(2) 0.1163(2) 0.1110(14) Uani 1 1 d D . . . .
B1 B 0.7640(4) 0.7547(3) 0.1317(3) 0.0663(16) Uani 1 1 d D . . . .
C2S C 0.2146(9) 0.9692(5) 0.5890(5) 0.168(5) Uani 1 1 d . U . . .
H2SA H 0.199845 0.975923 0.541129 0.252 Uiso 1 1 calc GR . . . .
H2SB H 0.154043 0.978841 0.612997 0.252 Uiso 1 1 calc GR . . . .
H2SC H 0.235302 0.922298 0.597170 0.252 Uiso 1 1 calc GR . . . .
C1S C 0.2975(5) 1.0154(3) 0.6128(4) 0.0922(19) Uani 1 1 d . U . . .
H1SA H 0.322700 1.001913 0.658100 0.111 Uiso 1 1 calc R . . . .
H1SB H 0.354079 1.011844 0.582924 0.111 Uiso 1 1 calc R . . . .
O1S O 0.2621(3) 1.0848(2) 0.6139(2) 0.0889(12) Uani 1 1 d . U . . .
C3S C 0.3272(6) 1.1286(4) 0.6422(4) 0.106(2) Uani 1 1 d . U . . .
H3SA H 0.385935 1.133166 0.614276 0.127 Uiso 1 1 calc R . . . .
H3SB H 0.351849 1.111300 0.686325 0.127 Uiso 1 1 calc R . . . .
C4S C 0.2787(7) 1.1976(4) 0.6505(5) 0.127(3) Uani 1 1 d . U . . .
H4SA H 0.217537 1.200902 0.621093 0.191 Uiso 1 1 calc GR . . . .
H4SB H 0.326264 1.232996 0.639024 0.191 Uiso 1 1 calc GR . . . .
H4SC H 0.261159 1.203350 0.696898 0.191 Uiso 1 1 calc GR . . . .
F4A F 0.692(2) 0.7519(17) 0.0779(13) 0.1222(18) Uani 0.091(5) 1 d D . P C 2
F3A F 0.796(2) 0.6923(8) 0.142(2) 0.124(2) Uani 0.091(5) 1 d D . P C 2
F2A F 0.711(2) 0.7782(14) 0.1856(14) 0.0963(16) Uani 0.091(5) 1 d D . P C 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 C16 1.737(3) . ?
S1 C15 1.738(3) . ?
O6 C45 1.381(4) . ?
O6 C46 1.427(4) . ?
O4 C38 1.421(4) . ?
O4 C37 1.415(4) . ?
O2 C33 1.370(4) . ?
O2 C34 1.432(4) . ?
O5 C40 1.370(4) . ?
O5 C39 1.435(4) . ?
O3 C36 1.435(4) . ?
O3 C35 1.428(4) . ?
O1 C28 1.373(4) . ?
O1 C51 1.431(4) . ?
O7 C47 1.419(4) . ?
O7 C48 1.432(4) . ?
N1 H1 0.8800 . ?
N1 C7 1.333(4) . ?
N1 C18 1.391(4) . ?
N2 H2 0.8800 . ?
N2 C8 1.384(4) . ?
N2 C7 1.334(4) . ?
C16 C17 1.489(4) . ?
C16 C9 1.363(4) . ?
C8 C18 1.363(4) . ?
C8 C9 1.466(4) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C7 C1 1.460(4) . ?
C18 C19 1.462(4) . ?
C18 C19A 1.59(2) . ?
C6 H6 0.9500 . ?
C6 C1 1.394(4) . ?
C6 C5 1.384(4) . ?
C1 C2 1.391(4) . ?
C10 C9 1.447(4) . ?
C10 C11 1.404(5) . ?
C10 C15 1.400(4) . ?
C4 H4 0.9500 . ?
C4 C3 1.377(5) . ?
C4 C5 1.382(5) . ?
C45 C40 1.404(5) . ?
C45 C44 1.379(5) . ?
C2 H2A 0.9500 . ?
C2 C3 1.388(5) . ?
C3 H3 0.9500 . ?
C36 H36A 0.9900 . ?
C36 H36B 0.9900 . ?
C36 C37 1.500(5) . ?
C28 C33 1.406(5) . ?
C28 C29 1.385(5) . ?
C40 C41 1.399(5) . ?
C38 H38A 0.9900 . ?
C38 H38B 0.9900 . ?
C38 C39 1.495(6) . ?
C47 H47A 0.9900 . ?
C47 H47B 0.9900 . ?
C47 C46 1.495(5) . ?
C32 H32 0.9500 . ?
C32 C33 1.382(5) . ?
C32 C31 1.400(6) . ?
C5 H5 0.9500 . ?
C14 H14 0.9500 . ?
C14 C15 1.397(5) . ?
C14 C13 1.379(5) . ?
C39 H39A 0.9900 . ?
C39 H39B 0.9900 . ?
C48 H48A 0.9900 . ?
C48 H48B 0.9900 . ?
C48 H48C 0.9900 . ?
C48 H48D 0.9900 . ?
C48 C49 1.507(6) . ?
C48 C49A 1.474(13) . ?
C41 H41 0.9500 . ?
C41 C42 1.391(6) . ?
C11 H11 0.9500 . ?
C11 C12 1.379(5) . ?
C37 H37A 0.9900 . ?
C37 H37B 0.9900 . ?
C13 H13 0.9500 . ?
C13 C12 1.403(6) . ?
C34 H34A 0.9900 . ?
C34 H34B 0.9900 . ?
C34 C35 1.491(6) . ?
C51 H51A 0.9900 . ?
C51 H51B 0.9900 . ?
C51 H51C 0.9900 . ?
C51 H51D 0.9900 . ?
C51 C50 1.433(6) . ?
C51 C50A 1.359(13) . ?
C43 H43 0.9500 . ?
C43 C44 1.395(6) . ?
C43 C42 1.375(7) . ?
C29 H29 0.9500 . ?
C29 C30 1.380(6) . ?
C46 H46A 0.9900 . ?
C46 H46B 0.9900 . ?
C12 H12 0.9500 . ?
C44 H44 0.9500 . ?
C35 H35A 0.9900 . ?
C35 H35B 0.9900 . ?
C30 H30 0.9500 . ?
C30 C31 1.372(7) . ?
C42 H42 0.9500 . ?
C31 H31 0.9500 . ?
S2 C26 1.734(4) . ?
S2 C25 1.707(5) . ?
C19 C26 1.367(5) . ?
C19 C20 1.436(5) . ?
C26 C27 1.479(5) . ?
C20 C21 1.407(5) . ?
C20 C25 1.408(5) . ?
C21 H21 0.9500 . ?
C21 C22 1.383(6) . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C25 C24 1.412(6) . ?
C24 H24 0.9500 . ?
C24 C23 1.358(8) . ?
C23 H23 0.9500 . ?
C23 C22 1.402(7) . ?
C22 H22 0.9500 . ?
O8 C50 1.426(12) . ?
O8 C49 1.384(12) . ?
C50 H50A 0.9900 . ?
C50 H50B 0.9900 . ?
C49 H49A 0.9900 . ?
C49 H49B 0.9900 . ?
S2A C26A 1.730(17) . ?
S2A C25A 1.717(16) . ?
C19A C26A 1.366(17) . ?
C19A C20A 1.430(15) . ?
C26A C27A 1.478(16) . ?
C20A C21A 1.405(16) . ?
C20A C25A 1.414(16) . ?
C21A H21A 0.9500 . ?
C21A C22A 1.384(18) . ?
C27A H27D 0.9800 . ?
C27A H27E 0.9800 . ?
C27A H27F 0.9800 . ?
C25A C24A 1.408(16) . ?
C24A H24A 0.9500 . ?
C24A C23A 1.360(18) . ?
C23A H23A 0.9500 . ?
C23A C22A 1.400(19) . ?
C22A H22A 0.9500 . ?
O8A C50A 1.42(3) . ?
O8A C49A 1.43(3) . ?
C50A H50C 0.9900 . ?
C50A H50D 0.9900 . ?
C49A H49C 0.9900 . ?
C49A H49D 0.9900 . ?
F4 B1 1.395(8) . ?
F3 B1 1.365(7) . ?
F2 B1 1.358(6) . ?
F1 B1 1.360(7) . ?
B1 F4A 1.403(17) . ?
B1 F3A 1.317(15) . ?
B1 F2A 1.405(15) . ?
C2S H2SA 0.9800 . ?
C2S H2SB 0.9800 . ?
C2S H2SC 0.9800 . ?
C2S C1S 1.491(11) . ?
C1S H1SA 0.9900 . ?
C1S H1SB 0.9900 . ?
C1S O1S 1.455(7) . ?
O1S C3S 1.330(8) . ?
C3S H3SA 0.9900 . ?
C3S H3SB 0.9900 . ?
C3S C4S 1.526(11) . ?
C4S H4SA 0.9800 . ?
C4S H4SB 0.9800 . ?
C4S H4SC 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
C16 S1 C15 92.37(15) . . ?
C45 O6 C46 116.0(3) . . ?
C37 O4 C38 110.9(3) . . ?
C33 O2 C34 117.0(3) . . ?
C40 O5 C39 116.3(3) . . ?
C35 O3 C36 112.3(3) . . ?
C28 O1 C51 117.5(3) . . ?
C47 O7 C48 111.5(3) . . ?
C7 N1 H1 125.0 . . ?
C7 N1 C18 109.9(2) . . ?
C18 N1 H1 125.0 . . ?
C8 N2 H2 125.0 . . ?
C7 N2 H2 125.0 . . ?
C7 N2 C8 109.9(2) . . ?
C17 C16 S1 119.1(2) . . ?
C9 C16 S1 111.8(2) . . ?
C9 C16 C17 129.1(3) . . ?
N2 C8 C9 122.5(3) . . ?
C18 C8 N2 106.6(3) . . ?
C18 C8 C9 130.9(3) . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
N1 C7 N2 107.3(3) . . ?
N1 C7 C1 126.2(3) . . ?
N2 C7 C1 126.5(3) . . ?
N1 C18 C19 122.4(3) . . ?
N1 C18 C19A 108.4(13) . . ?
C8 C18 N1 106.2(3) . . ?
C8 C18 C19 131.3(3) . . ?
C8 C18 C19A 143.1(14) . . ?
C1 C6 H6 120.5 . . ?
C5 C6 H6 120.5 . . ?
C5 C6 C1 118.9(3) . . ?
C6 C1 C7 119.4(3) . . ?
C2 C1 C7 120.0(3) . . ?
C2 C1 C6 120.7(3) . . ?
C11 C10 C9 128.5(3) . . ?
C15 C10 C9 112.1(3) . . ?
C15 C10 C11 119.3(3) . . ?
C16 C9 C8 123.7(3) . . ?
C16 C9 C10 113.0(3) . . ?
C10 C9 C8 123.1(3) . . ?
C3 C4 H4 119.5 . . ?
C3 C4 C5 120.9(3) . . ?
C5 C4 H4 119.5 . . ?
O6 C45 C40 115.6(3) . . ?
C44 C45 O6 124.1(3) . . ?
C44 C45 C40 120.3(3) . . ?
C1 C2 H2A 120.2 . . ?
C3 C2 C1 119.6(3) . . ?
C3 C2 H2A 120.2 . . ?
C4 C3 C2 119.6(3) . . ?
C4 C3 H3 120.2 . . ?
C2 C3 H3 120.2 . . ?
O3 C36 H36A 109.6 . . ?
O3 C36 H36B 109.6 . . ?
O3 C36 C37 110.2(3) . . ?
H36A C36 H36B 108.1 . . ?
C37 C36 H36A 109.6 . . ?
C37 C36 H36B 109.6 . . ?
O1 C28 C33 115.8(3) . . ?
O1 C28 C29 124.5(3) . . ?
C29 C28 C33 119.6(3) . . ?
O5 C40 C45 116.8(3) . . ?
O5 C40 C41 124.1(3) . . ?
C41 C40 C45 119.1(3) . . ?
O4 C38 H38A 109.7 . . ?
O4 C38 H38B 109.7 . . ?
O4 C38 C39 109.6(3) . . ?
H38A C38 H38B 108.2 . . ?
C39 C38 H38A 109.7 . . ?
C39 C38 H38B 109.7 . . ?
O7 C47 H47A 109.8 . . ?
O7 C47 H47B 109.8 . . ?
O7 C47 C46 109.3(3) . . ?
H47A C47 H47B 108.3 . . ?
C46 C47 H47A 109.8 . . ?
C46 C47 H47B 109.8 . . ?
C33 C32 H32 119.8 . . ?
C33 C32 C31 120.4(4) . . ?
C31 C32 H32 119.8 . . ?
O2 C33 C28 116.2(3) . . ?
O2 C33 C32 124.8(3) . . ?
C32 C33 C28 119.0(3) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 C6 120.3(3) . . ?
C4 C5 H5 119.9 . . ?
C15 C14 H14 120.8 . . ?
C13 C14 H14 120.8 . . ?
C13 C14 C15 118.4(3) . . ?
O5 C39 C38 109.0(3) . . ?
O5 C39 H39A 109.9 . . ?
O5 C39 H39B 109.9 . . ?
C38 C39 H39A 109.9 . . ?
C38 C39 H39B 109.9 . . ?
H39A C39 H39B 108.3 . . ?
O7 C48 H48A 109.7 . . ?
O7 C48 H48B 109.7 . . ?
O7 C48 H48C 107.5 . . ?
O7 C48 H48D 107.5 . . ?
O7 C48 C49 109.9(3) . . ?
O7 C48 C49A 119.2(5) . . ?
H48A C48 H48B 108.2 . . ?
H48C C48 H48D 107.0 . . ?
C49 C48 H48A 109.7 . . ?
C49 C48 H48B 109.7 . . ?
C49A C48 H48C 107.5 . . ?
C49A C48 H48D 107.5 . . ?
C40 C41 H41 120.1 . . ?
C42 C41 C40 119.8(4) . . ?
C42 C41 H41 120.1 . . ?
C10 C11 H11 120.3 . . ?
C12 C11 C10 119.3(4) . . ?
C12 C11 H11 120.3 . . ?
O4 C37 C36 109.9(3) . . ?
O4 C37 H37A 109.7 . . ?
O4 C37 H37B 109.7 . . ?
C36 C37 H37A 109.7 . . ?
C36 C37 H37B 109.7 . . ?
H37A C37 H37B 108.2 . . ?
C10 C15 S1 110.7(2) . . ?
C14 C15 S1 127.8(3) . . ?
C14 C15 C10 121.5(3) . . ?
C14 C13 H13 119.5 . . ?
C14 C13 C12 120.9(3) . . ?
C12 C13 H13 119.5 . . ?
O2 C34 H34A 110.0 . . ?
O2 C34 H34B 110.0 . . ?
O2 C34 C35 108.3(3) . . ?
H34A C34 H34B 108.4 . . ?
C35 C34 H34A 110.0 . . ?
C35 C34 H34B 110.0 . . ?
O1 C51 H51A 107.7 . . ?
O1 C51 H51B 107.7 . . ?
O1 C51 H51C 108.4 . . ?
O1 C51 H51D 108.4 . . ?
O1 C51 C50 118.3(4) . . ?
H51A C51 H51B 107.1 . . ?
H51C C51 H51D 107.5 . . ?
C50 C51 H51A 107.7 . . ?
C50 C51 H51B 107.7 . . ?
C50A C51 O1 115.4(6) . . ?
C50A C51 H51C 108.4 . . ?
C50A C51 H51D 108.4 . . ?
C44 C43 H43 120.1 . . ?
C42 C43 H43 120.1 . . ?
C42 C43 C44 119.8(4) . . ?
C28 C29 H29 119.5 . . ?
C30 C29 C28 121.0(4) . . ?
C30 C29 H29 119.5 . . ?
O6 C46 C47 109.2(3) . . ?
O6 C46 H46A 109.8 . . ?
O6 C46 H46B 109.8 . . ?
C47 C46 H46A 109.8 . . ?
C47 C46 H46B 109.8 . . ?
H46A C46 H46B 108.3 . . ?
C11 C12 C13 120.7(4) . . ?
C11 C12 H12 119.7 . . ?
C13 C12 H12 119.7 . . ?
C45 C44 C43 120.3(4) . . ?
C45 C44 H44 119.9 . . ?
C43 C44 H44 119.9 . . ?
O3 C35 C34 109.8(3) . . ?
O3 C35 H35A 109.7 . . ?
O3 C35 H35B 109.7 . . ?
C34 C35 H35A 109.7 . . ?
C34 C35 H35B 109.7 . . ?
H35A C35 H35B 108.2 . . ?
C29 C30 H30 120.2 . . ?
C31 C30 C29 119.6(4) . . ?
C31 C30 H30 120.2 . . ?
C41 C42 H42 119.6 . . ?
C43 C42 C41 120.8(4) . . ?
C43 C42 H42 119.6 . . ?
C32 C31 H31 119.8 . . ?
C30 C31 C32 120.3(4) . . ?
C30 C31 H31 119.8 . . ?
C25 S2 C26 91.86(19) . . ?
C26 C19 C18 123.7(3) . . ?
C26 C19 C20 112.7(3) . . ?
C20 C19 C18 123.5(3) . . ?
C19 C26 S2 112.1(3) . . ?
C19 C26 C27 129.5(3) . . ?
C27 C26 S2 118.4(3) . . ?
C21 C20 C19 129.5(3) . . ?
C21 C20 C25 119.3(4) . . ?
C25 C20 C19 111.1(3) . . ?
C20 C21 H21 120.4 . . ?
C22 C21 C20 119.2(4) . . ?
C22 C21 H21 120.4 . . ?
C26 C27 H27A 109.5 . . ?
C26 C27 H27B 109.5 . . ?
C26 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C20 C25 S2 112.2(3) . . ?
C20 C25 C24 120.9(4) . . ?
C24 C25 S2 126.9(3) . . ?
C25 C24 H24 121.0 . . ?
C23 C24 C25 118.1(5) . . ?
C23 C24 H24 121.0 . . ?
C24 C23 H23 118.9 . . ?
C24 C23 C22 122.2(4) . . ?
C22 C23 H23 118.9 . . ?
C21 C22 C23 120.2(4) . . ?
C21 C22 H22 119.9 . . ?
C23 C22 H22 119.9 . . ?
C49 O8 C50 114.3(6) . . ?
C51 C50 H50A 109.2 . . ?
C51 C50 H50B 109.2 . . ?
O8 C50 C51 112.1(5) . . ?
O8 C50 H50A 109.2 . . ?
O8 C50 H50B 109.2 . . ?
H50A C50 H50B 107.9 . . ?
C48 C49 H49A 109.4 . . ?
C48 C49 H49B 109.4 . . ?
O8 C49 C48 111.2(5) . . ?
O8 C49 H49A 109.4 . . ?
O8 C49 H49B 109.4 . . ?
H49A C49 H49B 108.0 . . ?
C25A S2A C26A 91.8(8) . . ?
C26A C19A C18 135.2(17) . . ?
C26A C19A C20A 113.1(12) . . ?
C20A C19A C18 111.6(17) . . ?
C19A C26A S2A 112.0(10) . . ?
C19A C26A C27A 129.0(17) . . ?
C27A C26A S2A 118.9(15) . . ?
C21A C20A C19A 129.1(14) . . ?
C21A C20A C25A 119.7(12) . . ?
C25A C20A C19A 111.2(11) . . ?
C20A C21A H21A 120.8 . . ?
C22A C21A C20A 118.5(15) . . ?
C22A C21A H21A 120.8 . . ?
C26A C27A H27D 109.5 . . ?
C26A C27A H27E 109.5 . . ?
C26A C27A H27F 109.5 . . ?
H27D C27A H27E 109.5 . . ?
H27D C27A H27F 109.5 . . ?
H27E C27A H27F 109.5 . . ?
C20A C25A S2A 111.4(10) . . ?
C24A C25A S2A 127.3(13) . . ?
C24A C25A C20A 120.6(13) . . ?
C25A C24A H24A 121.1 . . ?
C23A C24A C25A 117.7(15) . . ?
C23A C24A H24A 121.1 . . ?
C24A C23A H23A 118.7 . . ?
C24A C23A C22A 122.6(15) . . ?
C22A C23A H23A 118.7 . . ?
C21A C22A C23A 120.2(15) . . ?
C21A C22A H22A 119.9 . . ?
C23A C22A H22A 119.9 . . ?
C50A O8A C49A 112(2) . . ?
C51 C50A O8A 118.5(16) . . ?
C51 C50A H50C 107.7 . . ?
C51 C50A H50D 107.7 . . ?
O8A C50A H50C 107.7 . . ?
O8A C50A H50D 107.7 . . ?
H50C C50A H50D 107.1 . . ?
C48 C49A H49C 109.8 . . ?
C48 C49A H49D 109.8 . . ?
O8A C49A C48 109.3(15) . . ?
O8A C49A H49C 109.8 . . ?
O8A C49A H49D 109.8 . . ?
H49C C49A H49D 108.3 . . ?
F3 B1 F4 104.9(5) . . ?
F2 B1 F4 108.9(6) . . ?
F2 B1 F3 111.4(5) . . ?
F2 B1 F1 111.2(5) . . ?
F1 B1 F4 107.0(5) . . ?
F1 B1 F3 113.0(6) . . ?
F1 B1 F4A 106.3(13) . . ?
F1 B1 F2A 107.8(12) . . ?
F4A B1 F2A 105.1(14) . . ?
F3A B1 F1 119.1(13) . . ?
F3A B1 F4A 106.3(15) . . ?
F3A B1 F2A 111.4(15) . . ?
H2SA C2S H2SB 109.5 . . ?
H2SA C2S H2SC 109.5 . . ?
H2SB C2S H2SC 109.5 . . ?
C1S C2S H2SA 109.5 . . ?
C1S C2S H2SB 109.5 . . ?
C1S C2S H2SC 109.5 . . ?
C2S C1S H1SA 109.5 . . ?
C2S C1S H1SB 109.5 . . ?
H1SA C1S H1SB 108.1 . . ?
O1S C1S C2S 110.7(7) . . ?
O1S C1S H1SA 109.5 . . ?
O1S C1S H1SB 109.5 . . ?
C3S O1S C1S 114.8(6) . . ?
O1S C3S H3SA 109.4 . . ?
O1S C3S H3SB 109.4 . . ?
O1S C3S C4S 111.3(6) . . ?
H3SA C3S H3SB 108.0 . . ?
C4S C3S H3SA 109.4 . . ?
C4S C3S H3SB 109.4 . . ?
C3S C4S H4SA 109.5 . . ?
C3S C4S H4SB 109.5 . . ?
C3S C4S H4SC 109.5 . . ?
H4SA C4S H4SB 109.5 . . ?
H4SA C4S H4SC 109.5 . . ?
H4SB C4S H4SC 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
S1 C16 C9 C8 -177.4(2) . . . . ?
S1 C16 C9 C10 -1.6(3) . . . . ?
O6 C45 C40 O5 -4.2(4) . . . . ?
O6 C45 C40 C41 175.6(3) . . . . ?
O6 C45 C44 C43 -175.8(3) . . . . ?
O4 C38 C39 O5 -85.3(3) . . . . ?
O2 C34 C35 O3 61.6(4) . . . . ?
O5 C40 C41 C42 -179.2(3) . . . . ?
O3 C36 C37 O4 62.1(4) . . . . ?
O1 C28 C33 O2 -3.4(5) . . . . ?
O1 C28 C33 C32 178.8(3) . . . . ?
O1 C28 C29 C30 -178.9(4) . . . . ?
O1 C51 C50 O8 61.0(8) . . . . ?
O1 C51 C50A O8A -57.0(14) . . . . ?
O7 C47 C46 O6 72.5(4) . . . . ?
O7 C48 C49 O8 -66.9(7) . . . . ?
O7 C48 C49A O8A 50.1(14) . . . . ?
N1 C7 C1 C6 41.8(4) . . . . ?
N1 C7 C1 C2 -136.1(3) . . . . ?
N1 C18 C19 C26 -128.8(4) . . . . ?
N1 C18 C19 C20 48.4(5) . . . . ?
N1 C18 C19A C26A 51(3) . . . . ?
N1 C18 C19A C20A -125(2) . . . . ?
N2 C8 C18 N1 1.2(3) . . . . ?
N2 C8 C18 C19 -174.7(3) . . . . ?
N2 C8 C18 C19A 160.4(18) . . . . ?
N2 C8 C9 C16 -125.1(3) . . . . ?
N2 C8 C9 C10 59.5(4) . . . . ?
N2 C7 C1 C6 -140.5(3) . . . . ?
N2 C7 C1 C2 41.6(4) . . . . ?
C16 S1 C15 C10 -1.0(2) . . . . ?
C16 S1 C15 C14 175.8(3) . . . . ?
C8 N2 C7 N1 0.2(3) . . . . ?
C8 N2 C7 C1 -177.9(3) . . . . ?
C8 C18 C19 C26 46.4(6) . . . . ?
C8 C18 C19 C20 -136.4(4) . . . . ?
C8 C18 C19A C26A -108(3) . . . . ?
C8 C18 C19A C20A 76(3) . . . . ?
C17 C16 C9 C8 0.0(5) . . . . ?
C17 C16 C9 C10 175.8(3) . . . . ?
C7 N1 C18 C8 -1.1(3) . . . . ?
C7 N1 C18 C19 175.2(3) . . . . ?
C7 N1 C18 C19A -168.1(13) . . . . ?
C7 N2 C8 C18 -0.9(3) . . . . ?
C7 N2 C8 C9 178.6(3) . . . . ?
C7 C1 C2 C3 177.6(3) . . . . ?
C18 N1 C7 N2 0.6(3) . . . . ?
C18 N1 C7 C1 178.6(3) . . . . ?
C18 C8 C9 C16 54.2(5) . . . . ?
C18 C8 C9 C10 -121.2(4) . . . . ?
C18 C19 C26 S2 175.9(3) . . . . ?
C18 C19 C26 C27 -3.1(6) . . . . ?
C18 C19 C20 C21 5.3(7) . . . . ?
C18 C19 C20 C25 -175.7(4) . . . . ?
C18 C19A C26A S2A -179(4) . . . . ?
C18 C19A C26A C27A 5(4) . . . . ?
C18 C19A C20A C21A -8(6) . . . . ?
C18 C19A C20A C25A 174(3) . . . . ?
C6 C1 C2 C3 -0.3(5) . . . . ?
C1 C6 C5 C4 -0.1(5) . . . . ?
C1 C2 C3 C4 -0.9(5) . . . . ?
C10 C11 C12 C13 1.0(7) . . . . ?
C9 C8 C18 N1 -178.2(3) . . . . ?
C9 C8 C18 C19 6.0(6) . . . . ?
C9 C8 C18 C19A -19.0(19) . . . . ?
C9 C10 C11 C12 175.1(4) . . . . ?
C9 C10 C15 S1 0.3(3) . . . . ?
C9 C10 C15 C14 -176.7(3) . . . . ?
C45 O6 C46 C47 171.2(3) . . . . ?
C45 C40 C41 C42 1.1(5) . . . . ?
C3 C4 C5 C6 -1.1(5) . . . . ?
C36 O3 C35 C34 165.4(3) . . . . ?
C28 O1 C51 C50 96.6(5) . . . . ?
C28 O1 C51 C50A 160.0(7) . . . . ?
C28 C29 C30 C31 -0.3(6) . . . . ?
C40 O5 C39 C38 -174.7(3) . . . . ?
C40 C45 C44 C43 2.1(5) . . . . ?
C40 C41 C42 C43 0.8(6) . . . . ?
C38 O4 C37 C36 169.2(3) . . . . ?
C47 O7 C48 C49 -161.6(3) . . . . ?
C47 O7 C48 C49A 134.4(7) . . . . ?
C33 O2 C34 C35 177.2(3) . . . . ?
C33 C28 C29 C30 1.3(6) . . . . ?
C33 C32 C31 C30 0.4(6) . . . . ?
C5 C6 C1 C7 -177.1(3) . . . . ?
C5 C6 C1 C2 0.8(5) . . . . ?
C5 C4 C3 C2 1.6(5) . . . . ?
C14 C13 C12 C11 -0.3(7) . . . . ?
C39 O5 C40 C45 164.9(3) . . . . ?
C39 O5 C40 C41 -14.8(5) . . . . ?
C48 O7 C47 C46 172.5(3) . . . . ?
C11 C10 C9 C16 -175.2(3) . . . . ?
C11 C10 C9 C8 0.6(5) . . . . ?
C11 C10 C15 S1 176.7(3) . . . . ?
C11 C10 C15 C14 -0.3(5) . . . . ?
C37 O4 C38 C39 -177.2(3) . . . . ?
C15 S1 C16 C17 -176.2(2) . . . . ?
C15 S1 C16 C9 1.5(2) . . . . ?
C15 C10 C9 C16 0.9(4) . . . . ?
C15 C10 C9 C8 176.7(3) . . . . ?
C15 C10 C11 C12 -0.7(6) . . . . ?
C15 C14 C13 C12 -0.7(6) . . . . ?
C13 C14 C15 S1 -175.5(3) . . . . ?
C13 C14 C15 C10 1.0(5) . . . . ?
C34 O2 C33 C28 177.4(3) . . . . ?
C34 O2 C33 C32 -4.9(5) . . . . ?
C51 O1 C28 C33 152.8(3) . . . . ?
C51 O1 C28 C29 -27.1(5) . . . . ?
C29 C28 C33 O2 176.4(3) . . . . ?
C29 C28 C33 C32 -1.4(5) . . . . ?
C29 C30 C31 C32 -0.6(7) . . . . ?
C46 O6 C45 C40 -173.9(3) . . . . ?
C46 O6 C45 C44 4.1(5) . . . . ?
C44 C45 C40 O5 177.8(3) . . . . ?
C44 C45 C40 C41 -2.5(5) . . . . ?
C44 C43 C42 C41 -1.2(6) . . . . ?
C35 O3 C36 C37 161.0(3) . . . . ?
C42 C43 C44 C45 -0.2(6) . . . . ?
C31 C32 C33 O2 -177.1(3) . . . . ?
C31 C32 C33 C28 0.6(5) . . . . ?
S2 C25 C24 C23 -178.7(5) . . . . ?
C19 C20 C21 C22 -179.3(5) . . . . ?
C19 C20 C25 S2 -1.2(5) . . . . ?
C19 C20 C25 C24 178.0(5) . . . . ?
C26 S2 C25 C20 0.3(4) . . . . ?
C26 S2 C25 C24 -178.8(5) . . . . ?
C26 C19 C20 C21 -177.2(4) . . . . ?
C26 C19 C20 C25 1.8(5) . . . . ?
C20 C19 C26 S2 -1.6(4) . . . . ?
C20 C19 C26 C27 179.4(4) . . . . ?
C20 C21 C22 C23 0.0(9) . . . . ?
C20 C25 C24 C23 2.3(9) . . . . ?
C21 C20 C25 S2 177.9(4) . . . . ?
C21 C20 C25 C24 -3.0(7) . . . . ?
C25 S2 C26 C19 0.7(3) . . . . ?
C25 S2 C26 C27 179.9(3) . . . . ?
C25 C20 C21 C22 1.8(7) . . . . ?
C25 C24 C23 C22 -0.4(11) . . . . ?
C24 C23 C22 C21 -0.7(11) . . . . ?
C50 O8 C49 C48 -175.9(7) . . . . ?
C49 O8 C50 C51 165.1(7) . . . . ?
S2A C25A C24A C23A 176(4) . . . . ?
C19A C20A C21A C22A 175(4) . . . . ?
C19A C20A C25A S2A 7(5) . . . . ?
C19A C20A C25A C24A 177(4) . . . . ?
C26A S2A C25A C20A -7(4) . . . . ?
C26A S2A C25A C24A -177(4) . . . . ?
C26A C19A C20A C21A 176(4) . . . . ?
C26A C19A C20A C25A -2(4) . . . . ?
C20A C19A C26A S2A -3(3) . . . . ?
C20A C19A C26A C27A -180(2) . . . . ?
C20A C21A C22A C23A 9(7) . . . . ?
C20A C25A C24A C23A 6(7) . . . . ?
C21A C20A C25A S2A -172(4) . . . . ?
C21A C20A C25A C24A -1(7) . . . . ?
C25A S2A C26A C19A 6(3) . . . . ?
C25A S2A C26A C27A -177.1(17) . . . . ?
C25A C20A C21A C22A -7(6) . . . . ?
C25A C24A C23A C22A -4(7) . . . . ?
C24A C23A C22A C21A -3(8) . . . . ?
C50A O8A C49A C48 164.2(12) . . . . ?
C49A O8A C50A C51 -178.3(11) . . . . ?
C2S C1S O1S C3S 172.0(7) . . . . ?
C1S O1S C3S C4S -171.5(6) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetonitrile diethyl ether'
