# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_dm17172_0m
_audit_block_doi                 10.5517/ccdc.csd.cc20htn0
_database_code_depnum_ccdc_archive 'CCDC 1862252'
_audit_update_record             
;
2018-08-15 deposited with the CCDC.
2018-09-26 downloaded from the CCDC.
;
_audit_creation_date             2017-03-20
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.01.04 svn.r3372 for OlexSys, GUI svn.r5324)
;
_shelxl_version_number           2014-3
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C31 H28 F2 N2 O S'
_chemical_formula_sum            'C31 H28 F2 N2 O S'
_chemical_formula_weight         514.61
_chemical_absolute_configuration rmad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   9.0912(17)
_cell_length_b                   17.553(3)
_cell_length_c                   20.148(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3215.1(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3136
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      20.640
_cell_measurement_theta_min      2.331
_shelx_estimated_absorpt_T_max   0.980
_shelx_estimated_absorpt_T_min   0.974
_exptl_absorpt_coefficient_mu    0.134
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6151
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2008/1 (Bruker,2008) was used for absorption correction. wR2(int) was 0.0621 before and 0.0516 after correction. The Ratio of minimum to maximum transmission is 0.8250. The λ/2 correction factor is 0.0015.'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.063
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1080
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0773
_diffrn_reflns_av_unetI/netI     0.0804
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            25952
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.518
_diffrn_reflns_theta_min         2.022
_diffrn_ambient_temperature      296
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.784
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.997
_reflns_number_gt                3365
_reflns_number_total             7376
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.437
_refine_diff_density_min         -0.274
_refine_diff_density_rms         0.050
_refine_ls_abs_structure_details 
;
 Flack x determined using 1132 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.09(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.998
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     337
_refine_ls_number_reflns         7376
_refine_ls_number_restraints     36
_refine_ls_R_factor_all          0.1577
_refine_ls_R_factor_gt           0.0670
_refine_ls_restrained_S_all      1.025
_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)+(0.1173P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1780
_refine_ls_wR_factor_ref         0.2264
_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
Uanis(C26) \\sim Ueq, Uanis(C31) \\sim Ueq, Uanis(C30) \\sim Ueq, Uanis(C29)
\\sim Ueq, Uanis(C28) \\sim Ueq, Uanis(C27) \\sim Ueq: with sigma of 0.005 and
sigma for terminal atoms of 0.01
3.a Ternary CH refined with riding coordinates:
 C1(H1), C14(H14)
3.b Aromatic/amide H refined with riding coordinates:
 N2(H2), C3(H3), C4(H4), C6(H6), C9(H9), C11(H11), C12(H12), C21(H21),
 C22(H22), C23(H23), C24(H24), C25(H25), C27(H27), C28(H28), C29(H29), C30(H30),
  C31(H31)
3.c Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C17(H17A,H17B,H17C), C18(H18A,H18B,H18C)
;
_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 0.10499(14) 0.81562(9) 0.46707(8) 0.0618(5) Uani 1 1 d . . . . .
F1 F 0.1384(9) 0.5221(4) 0.1200(3) 0.177(3) Uani 1 1 d . . . . .
F2 F 0.2356(8) 0.4082(3) 0.4522(3) 0.144(2) Uani 1 1 d . . . . .
O1 O 0.0400(4) 0.7718(3) 0.5240(2) 0.0769(13) Uani 1 1 d . . . . .
N1 N 0.2731(5) 0.8079(3) 0.2968(2) 0.0621(14) Uani 1 1 d . . . . .
N2 N 0.2413(4) 0.7680(3) 0.4321(2) 0.0576(13) Uani 1 1 d . . . . .
H2 H 0.3310 0.7741 0.4446 0.069 Uiso 1 1 calc R . . . .
C1 C 0.2985(6) 0.7294(4) 0.3176(3) 0.0543(15) Uani 1 1 d . . . . .
H1 H 0.4024 0.7221 0.3288 0.065 Uiso 1 1 calc R . . . .
C2 C 0.2546(7) 0.6755(4) 0.2641(3) 0.0666(17) Uani 1 1 d . . . . .
C3 C 0.2504(10) 0.6982(6) 0.1972(4) 0.102(3) Uani 1 1 d . . . . .
H3 H 0.2716 0.7484 0.1860 0.123 Uiso 1 1 calc R . . . .
C4 C 0.2154(14) 0.6472(8) 0.1487(5) 0.129(4) Uani 1 1 d . . . . .
H4 H 0.2158 0.6609 0.1041 0.155 Uiso 1 1 calc R . . . .
C5 C 0.1790(13) 0.5733(7) 0.1689(6) 0.123(4) Uani 1 1 d . . . . .
C6 C 0.1815(9) 0.5484(6) 0.2314(5) 0.096(3) Uani 1 1 d . . . . .
H6 H 0.1581 0.4982 0.2416 0.115 Uiso 1 1 calc R . . . .
C7 C 0.2199(7) 0.5992(4) 0.2800(3) 0.0696(18) Uani 1 1 d . . . . .
C8 C 0.2252(6) 0.5768(4) 0.3502(3) 0.0631(17) Uani 1 1 d . . . . .
C9 C 0.2313(9) 0.5003(5) 0.3692(5) 0.088(2) Uani 1 1 d . . . . .
H9 H 0.2393 0.4621 0.3374 0.106 Uiso 1 1 calc R . . . .
C10 C 0.2256(10) 0.4824(5) 0.4344(6) 0.097(3) Uani 1 1 d . . . . .
C11 C 0.2103(8) 0.5345(5) 0.4837(5) 0.091(2) Uani 1 1 d . . . . .
H11 H 0.2051 0.5195 0.5279 0.109 Uiso 1 1 calc R . . . .
C12 C 0.2029(6) 0.6100(4) 0.4663(4) 0.0643(17) Uani 1 1 d . . . . .
H12 H 0.1913 0.6466 0.4993 0.077 Uiso 1 1 calc R . . . .
C13 C 0.2123(5) 0.6331(4) 0.3999(3) 0.0537(15) Uani 1 1 d . . . . .
C14 C 0.2021(5) 0.7150(3) 0.3789(3) 0.0520(15) Uani 1 1 d . . . . .
H14 H 0.0998 0.7251 0.3664 0.062 Uiso 1 1 calc R . . . .
C15 C 0.2117(7) 0.8912(4) 0.5050(4) 0.0736(19) Uani 1 1 d . . . . .
C16 C 0.3165(8) 0.8586(5) 0.5580(4) 0.093(3) Uani 1 1 d . . . . .
H16A H 0.2613 0.8286 0.5891 0.140 Uiso 1 1 calc GR . . . .
H16B H 0.3641 0.8997 0.5810 0.140 Uiso 1 1 calc GR . . . .
H16C H 0.3893 0.8272 0.5370 0.140 Uiso 1 1 calc GR . . . .
C17 C 0.0980(8) 0.9429(4) 0.5379(5) 0.098(2) Uani 1 1 d . . . . .
H17A H 0.0218 0.9548 0.5066 0.147 Uiso 1 1 calc GR . . . .
H17B H 0.1447 0.9891 0.5523 0.147 Uiso 1 1 calc GR . . . .
H17C H 0.0560 0.9172 0.5755 0.147 Uiso 1 1 calc GR . . . .
C18 C 0.2939(10) 0.9350(5) 0.4513(5) 0.110(3) Uani 1 1 d . . . . .
H18A H 0.3713 0.9037 0.4337 0.166 Uiso 1 1 calc GR . . . .
H18B H 0.3354 0.9805 0.4699 0.166 Uiso 1 1 calc GR . . . .
H18C H 0.2270 0.9483 0.4163 0.166 Uiso 1 1 calc GR . . . .
C19 C 0.3779(7) 0.8520(4) 0.2834(3) 0.0605(16) Uani 1 1 d . . . . .
C20 C 0.5407(6) 0.8329(4) 0.2837(3) 0.0644(17) Uani 1 1 d . . . . .
C21 C 0.6098(9) 0.8182(5) 0.2233(4) 0.093(2) Uani 1 1 d . . . . .
H21 H 0.5559 0.8173 0.1841 0.111 Uiso 1 1 calc R . . . .
C22 C 0.7618(9) 0.8049(6) 0.2226(6) 0.113(3) Uani 1 1 d . . . . .
H22 H 0.8086 0.7938 0.1827 0.135 Uiso 1 1 calc R . . . .
C23 C 0.8410(8) 0.8079(5) 0.2794(6) 0.106(3) Uani 1 1 d . . . . .
H23 H 0.9424 0.8007 0.2786 0.127 Uiso 1 1 calc R . . . .
C24 C 0.7719(8) 0.8213(6) 0.3363(5) 0.107(3) Uani 1 1 d . . . . .
H24 H 0.8258 0.8224 0.3755 0.129 Uiso 1 1 calc R . . . .
C25 C 0.6235(7) 0.8334(5) 0.3387(4) 0.095(3) Uani 1 1 d . . . . .
H25 H 0.5789 0.8423 0.3795 0.114 Uiso 1 1 calc R . . . .
C26 C 0.3423(7) 0.9319(4) 0.2647(3) 0.0686(18) Uani 1 1 d . U . . .
C27 C 0.4378(10) 0.9895(5) 0.2692(5) 0.109(3) Uani 1 1 d . U . . .
H27 H 0.5337 0.9790 0.2825 0.130 Uiso 1 1 calc R . . . .
C28 C 0.4009(12) 1.0622(6) 0.2554(5) 0.121(3) Uani 1 1 d . U . . .
H28 H 0.4706 1.1002 0.2620 0.145 Uiso 1 1 calc R . . . .
C29 C 0.2671(12) 1.0818(6) 0.2325(5) 0.119(3) Uani 1 1 d . U . . .
H29 H 0.2387 1.1324 0.2279 0.143 Uiso 1 1 calc R . . . .
C30 C 0.1722(14) 1.0210(7) 0.2156(7) 0.147(4) Uani 1 1 d . U . . .
H30 H 0.0858 1.0300 0.1923 0.176 Uiso 1 1 calc R . . . .
C31 C 0.2110(11) 0.9468(6) 0.2349(5) 0.121(3) Uani 1 1 d . U . . .
H31 H 0.1457 0.9070 0.2271 0.145 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O1 1.501(5) . ?
S1 N2 1.652(4) . ?
S1 C15 1.813(7) . ?
F1 C5 1.385(10) . ?
F2 C10 1.356(9) . ?
N1 C1 1.459(8) . ?
N1 C19 1.257(8) . ?
N2 H2 0.8600 . ?
N2 C14 1.463(7) . ?
C1 H1 0.9800 . ?
C1 C2 1.488(9) . ?
C1 C14 1.536(8) . ?
C2 C3 1.405(11) . ?
C2 C7 1.413(10) . ?
C3 H3 0.9300 . ?
C3 C4 1.364(13) . ?
C4 H4 0.9300 . ?
C4 C5 1.398(14) . ?
C5 C6 1.334(14) . ?
C6 H6 0.9300 . ?
C6 C7 1.371(10) . ?
C7 C8 1.468(10) . ?
C8 C9 1.399(10) . ?
C8 C13 1.411(9) . ?
C9 H9 0.9300 . ?
C9 C10 1.351(12) . ?
C10 C11 1.356(12) . ?
C11 H11 0.9300 . ?
C11 C12 1.373(10) . ?
C12 H12 0.9300 . ?
C12 C13 1.400(9) . ?
C13 C14 1.502(8) . ?
C14 H14 0.9800 . ?
C15 C16 1.542(10) . ?
C15 C17 1.526(10) . ?
C15 C18 1.523(11) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 C20 1.518(8) . ?
C19 C26 1.486(10) . ?
C20 C21 1.393(10) . ?
C20 C25 1.340(9) . ?
C21 H21 0.9300 . ?
C21 C22 1.401(11) . ?
C22 H22 0.9300 . ?
C22 C23 1.354(13) . ?
C23 H23 0.9300 . ?
C23 C24 1.328(13) . ?
C24 H24 0.9300 . ?
C24 C25 1.367(10) . ?
C25 H25 0.9300 . ?
C26 C27 1.336(10) . ?
C26 C31 1.362(11) . ?
C27 H27 0.9300 . ?
C27 C28 1.349(12) . ?
C28 H28 0.9300 . ?
C28 C29 1.346(14) . ?
C29 H29 0.9300 . ?
C29 C30 1.413(15) . ?
C30 H30 0.9300 . ?
C30 C31 1.404(14) . ?
C31 H31 0.9300 . ?

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
O1 S1 N2 111.2(3) . . ?
O1 S1 C15 105.3(3) . . ?
N2 S1 C15 98.6(3) . . ?
C19 N1 C1 121.6(5) . . ?
S1 N2 H2 121.6 . . ?
C14 N2 S1 116.9(3) . . ?
C14 N2 H2 121.6 . . ?
N1 C1 H1 110.0 . . ?
N1 C1 C2 110.5(5) . . ?
N1 C1 C14 107.2(5) . . ?
C2 C1 H1 110.0 . . ?
C2 C1 C14 109.0(5) . . ?
C14 C1 H1 110.0 . . ?
C3 C2 C1 121.4(7) . . ?
C3 C2 C7 118.7(7) . . ?
C7 C2 C1 119.8(6) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 C2 120.5(9) . . ?
C4 C3 H3 119.7 . . ?
C3 C4 H4 121.4 . . ?
C3 C4 C5 117.1(9) . . ?
C5 C4 H4 121.4 . . ?
F1 C5 C4 117.3(11) . . ?
C6 C5 F1 117.6(11) . . ?
C6 C5 C4 125.1(9) . . ?
C5 C6 H6 121.1 . . ?
C5 C6 C7 117.8(9) . . ?
C7 C6 H6 121.1 . . ?
C2 C7 C8 117.7(6) . . ?
C6 C7 C2 120.7(7) . . ?
C6 C7 C8 121.5(7) . . ?
C9 C8 C7 121.4(7) . . ?
C9 C8 C13 118.8(7) . . ?
C13 C8 C7 119.5(6) . . ?
C8 C9 H9 120.4 . . ?
C10 C9 C8 119.1(8) . . ?
C10 C9 H9 120.4 . . ?
F2 C10 C11 117.4(9) . . ?
C9 C10 F2 118.5(9) . . ?
C9 C10 C11 124.0(8) . . ?
C10 C11 H11 121.0 . . ?
C10 C11 C12 117.9(8) . . ?
C12 C11 H11 121.0 . . ?
C11 C12 H12 119.3 . . ?
C11 C12 C13 121.4(7) . . ?
C13 C12 H12 119.3 . . ?
C8 C13 C14 118.4(5) . . ?
C12 C13 C8 118.7(6) . . ?
C12 C13 C14 122.9(6) . . ?
N2 C14 C1 110.3(4) . . ?
N2 C14 C13 112.8(5) . . ?
N2 C14 H14 107.7 . . ?
C1 C14 H14 107.7 . . ?
C13 C14 C1 110.4(5) . . ?
C13 C14 H14 107.7 . . ?
C16 C15 S1 110.5(5) . . ?
C17 C15 S1 104.8(5) . . ?
C17 C15 C16 109.8(7) . . ?
C18 C15 S1 109.4(5) . . ?
C18 C15 C16 112.1(7) . . ?
C18 C15 C17 110.0(7) . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C15 C17 H17A 109.5 . . ?
C15 C17 H17B 109.5 . . ?
C15 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C15 C18 H18A 109.5 . . ?
C15 C18 H18B 109.5 . . ?
C15 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
N1 C19 C20 127.0(6) . . ?
N1 C19 C26 118.1(6) . . ?
C26 C19 C20 114.9(5) . . ?
C21 C20 C19 118.6(6) . . ?
C25 C20 C19 123.3(6) . . ?
C25 C20 C21 118.0(6) . . ?
C20 C21 H21 120.5 . . ?
C20 C21 C22 119.0(8) . . ?
C22 C21 H21 120.5 . . ?
C21 C22 H22 119.7 . . ?
C23 C22 C21 120.6(9) . . ?
C23 C22 H22 119.7 . . ?
C22 C23 H23 120.5 . . ?
C24 C23 C22 119.0(7) . . ?
C24 C23 H23 120.5 . . ?
C23 C24 H24 119.1 . . ?
C23 C24 C25 121.7(9) . . ?
C25 C24 H24 119.1 . . ?
C20 C25 C24 121.6(8) . . ?
C20 C25 H25 119.2 . . ?
C24 C25 H25 119.2 . . ?
C27 C26 C19 123.7(6) . . ?
C27 C26 C31 117.0(8) . . ?
C31 C26 C19 118.9(7) . . ?
C26 C27 H27 118.6 . . ?
C26 C27 C28 122.7(9) . . ?
C28 C27 H27 118.6 . . ?
C27 C28 H28 118.7 . . ?
C29 C28 C27 122.5(11) . . ?
C29 C28 H28 118.7 . . ?
C28 C29 H29 121.9 . . ?
C28 C29 C30 116.2(10) . . ?
C30 C29 H29 121.9 . . ?
C29 C30 H30 120.6 . . ?
C31 C30 C29 118.7(11) . . ?
C31 C30 H30 120.6 . . ?
C26 C31 C30 121.4(11) . . ?
C26 C31 H31 119.3 . . ?
C30 C31 H31 119.3 . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 -0.427 -0.250 0.000 404.3 113.3 ?
2 -0.058 0.250 0.500 404.3 113.3 ?

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

data_cd17233
_audit_block_doi                 10.5517/ccdc.csd.cc20htp1
_database_code_depnum_ccdc_archive 'CCDC 1862253'
_audit_update_record             
;
2018-08-15 deposited with the CCDC.
2018-09-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C31 H28 F2 N2 O S'
_chemical_formula_weight         514.61

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   11.2418(17)
_cell_length_b                   11.3491(16)
_cell_length_c                   11.7184(18)
_cell_angle_alpha                98.339(3)
_cell_angle_beta                 114.149(3)
_cell_angle_gamma                93.521(3)
_cell_volume                     1337.7(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2293
_cell_measurement_theta_min      4.810
_cell_measurement_theta_max      50.140

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.278
_exptl_crystal_F_000             540
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.162
_shelx_estimated_absorpt_T_min   0.968
_shelx_estimated_absorpt_T_max   0.984
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6315
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7414
_diffrn_reflns_av_unetI/netI     0.0435
_diffrn_reflns_av_R_equivalents  0.0232
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.830
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.972
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.972
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.972
_reflns_number_total             4701
_reflns_number_gt                3721
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 ? 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0546P)²+0.8157P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4701
_refine_ls_number_parameters     350
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0755
_refine_ls_R_factor_gt           0.0588
_refine_ls_wR_factor_ref         0.1492
_refine_ls_wR_factor_gt          0.1384
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.049
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.21889(7) 0.25114(7) 0.01491(6) 0.0571(2) Uani 1 1 d . . . . .
F1 F 0.16298(19) 0.00269(19) 0.57842(17) 0.0834(6) Uani 1 1 d . . . . .
F2 F 0.4838(2) -0.30888(17) 0.2448(2) 0.0957(7) Uani 1 1 d . . . . .
N1 N 0.2195(2) 0.1711(2) 0.1236(2) 0.0497(6) Uani 1 1 d . . . . .
N2 N 0.5567(2) 0.2474(2) 0.3883(2) 0.0498(5) Uani 1 1 d . . . . .
O1 O 0.3262(3) 0.2435(3) -0.0171(3) 0.0855(9) Uani 0.8 1 d . . P A 1
O1' O 0.2177(15) 0.3635(8) 0.0274(11) 0.100(5) Uani 0.2 1 d . . P A 2
C1 C 0.3247(3) 0.2147(2) 0.2543(2) 0.0479(6) Uani 1 1 d . . . . .
H1 H 0.3302 0.3022 0.2749 0.058 Uiso 1 1 calc R U . . .
C2 C 0.4578(3) 0.1834(2) 0.2624(2) 0.0487(6) Uani 1 1 d . . . . .
H2 H 0.4751 0.2107 0.1943 0.058 Uiso 1 1 calc R U . . .
C3 C 0.4597(2) 0.0494(2) 0.2526(2) 0.0448(6) Uani 1 1 d . . . . .
C4 C 0.3996(2) -0.0139(2) 0.3132(2) 0.0423(6) Uani 1 1 d . . . . .
C5 C 0.3229(2) 0.0488(2) 0.3740(2) 0.0416(6) Uani 1 1 d . . . . .
C6 C 0.2871(2) 0.1602(2) 0.3469(2) 0.0458(6) Uani 1 1 d . . . . .
C7 C 0.2119(3) 0.2171(3) 0.4006(3) 0.0627(8) Uani 1 1 d . . . . .
H7 H 0.1890 0.2920 0.3830 0.075 Uiso 1 1 calc R U . . .
C8 C 0.1702(3) 0.1658(3) 0.4792(3) 0.0690(9) Uani 1 1 d . . . . .
H8 H 0.1197 0.2047 0.5150 0.083 Uiso 1 1 calc R U . . .
C9 C 0.2052(3) 0.0562(3) 0.5030(2) 0.0579(8) Uani 1 1 d . . . . .
C10 C 0.2802(3) -0.0028(3) 0.4540(2) 0.0497(7) Uani 1 1 d . . . . .
H10 H 0.3030 -0.0771 0.4737 0.060 Uiso 1 1 calc R U . . .
C11 C 0.4098(3) -0.1353(2) 0.3102(3) 0.0545(7) Uani 1 1 d . . . . .
H11 H 0.3726 -0.1788 0.3515 0.065 Uiso 1 1 calc R U . . .
C12 C 0.4745(3) -0.1900(3) 0.2466(3) 0.0616(8) Uani 1 1 d . . . . .
C13 C 0.5300(3) -0.1322(3) 0.1830(3) 0.0648(8) Uani 1 1 d . . . . .
H13 H 0.5718 -0.1728 0.1384 0.078 Uiso 1 1 calc R U . . .
C14 C 0.5219(3) -0.0109(3) 0.1870(3) 0.0565(7) Uani 1 1 d . . . . .
H14 H 0.5592 0.0310 0.1445 0.068 Uiso 1 1 calc R U . . .
C15 C 0.6501(2) 0.3218(2) 0.3948(2) 0.0460(6) Uani 1 1 d . . . . .
C16 C 0.7414(3) 0.3912(2) 0.5229(2) 0.0483(6) Uani 1 1 d . . . . .
C17 C 0.6982(3) 0.4131(2) 0.6178(3) 0.0583(7) Uani 1 1 d . . . . .
H17 H 0.6116 0.3866 0.6006 0.070 Uiso 1 1 calc R U . . .
C18 C 0.7824(4) 0.4740(3) 0.7376(3) 0.0718(9) Uani 1 1 d . . . . .
H18 H 0.7530 0.4870 0.8014 0.086 Uiso 1 1 calc R U . . .
C19 C 0.9094(4) 0.5154(3) 0.7629(3) 0.0781(10) Uani 1 1 d . . . . .
H19 H 0.9659 0.5569 0.8438 0.094 Uiso 1 1 calc R U . . .
C20 C 0.9533(3) 0.4961(3) 0.6705(3) 0.0727(9) Uani 1 1 d . . . . .
H20 H 1.0396 0.5244 0.6882 0.087 Uiso 1 1 calc R U . . .
C21 C 0.8698(3) 0.4343(3) 0.5500(3) 0.0601(8) Uani 1 1 d . . . . .
H21 H 0.9001 0.4216 0.4869 0.072 Uiso 1 1 calc R U . . .
C22 C 0.6752(3) 0.3462(2) 0.2839(2) 0.0512(7) Uani 1 1 d . . . . .
C23 C 0.7301(3) 0.2670(3) 0.2262(3) 0.0734(9) Uani 1 1 d . . . . .
H23 H 0.7548 0.1974 0.2578 0.088 Uiso 1 1 calc R U . . .
C24 C 0.7488(5) 0.2893(5) 0.1227(4) 0.1071(16) Uani 1 1 d . . . . .
H24 H 0.7860 0.2349 0.0841 0.128 Uiso 1 1 calc R U . . .
C25 C 0.7131(5) 0.3908(6) 0.0763(4) 0.120(2) Uani 1 1 d . . . . .
H25 H 0.7247 0.4053 0.0052 0.144 Uiso 1 1 calc R U . . .
C26 C 0.6608(4) 0.4708(5) 0.1330(5) 0.1074(16) Uani 1 1 d . . . . .
H26 H 0.6373 0.5404 0.1011 0.129 Uiso 1 1 calc R U . . .
C27 C 0.6419(3) 0.4501(3) 0.2375(3) 0.0757(10) Uani 1 1 d . . . . .
H27 H 0.6068 0.5060 0.2767 0.091 Uiso 1 1 calc R U . . .
C28 C 0.0733(3) 0.1664(3) -0.1211(2) 0.0576(7) Uani 1 1 d . . . . .
C29 C 0.0683(4) 0.2229(3) -0.2322(3) 0.0824(11) Uani 1 1 d . . . . .
H29A H -0.0118 0.1907 -0.3058 0.124 Uiso 1 1 calc R U . . .
H29B H 0.1422 0.2056 -0.2500 0.124 Uiso 1 1 calc R U . . .
H29C H 0.0714 0.3084 -0.2111 0.124 Uiso 1 1 calc R U . . .
C30 C -0.0442(3) 0.1881(5) -0.0938(4) 0.1049(14) Uani 1 1 d . . . . .
H30A H -0.0480 0.2729 -0.0785 0.157 Uiso 1 1 calc R U . . .
H30B H -0.0363 0.1561 -0.0200 0.157 Uiso 1 1 calc R U . . .
H30C H -0.1230 0.1492 -0.1656 0.157 Uiso 1 1 calc R U . . .
C31 C 0.0887(5) 0.0353(3) -0.1448(3) 0.0999(14) Uani 1 1 d . . . . .
H31A H 0.0174 -0.0049 -0.2228 0.150 Uiso 1 1 calc R U . . .
H31B H 0.0880 -0.0005 -0.0756 0.150 Uiso 1 1 calc R U . . .
H31C H 0.1706 0.0277 -0.1509 0.150 Uiso 1 1 calc R U . . .
H1A H 0.234(3) 0.106(3) 0.097(3) 0.080(12) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O1' 1.264(10) . ?
S1 O1 1.406(3) . ?
S1 N1 1.666(2) . ?
S1 C28 1.836(3) . ?
F1 C9 1.356(3) . ?
F2 C12 1.357(3) . ?
N1 C1 1.489(3) . ?
N1 H1A 0.82(3) . ?
N2 C15 1.276(3) . ?
N2 C2 1.480(3) . ?
C1 C6 1.508(3) . ?
C1 C2 1.528(4) . ?
C1 H1 0.9800 . ?
C2 C3 1.511(4) . ?
C2 H2 0.9800 . ?
C3 C14 1.376(4) . ?
C3 C4 1.399(3) . ?
C4 C11 1.386(4) . ?
C4 C5 1.479(4) . ?
C5 C6 1.392(4) . ?
C5 C10 1.394(3) . ?
C6 C7 1.383(4) . ?
C7 C8 1.371(4) . ?
C7 H7 0.9300 . ?
C8 C9 1.360(4) . ?
C8 H8 0.9300 . ?
C9 C10 1.358(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.354(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.360(4) . ?
C13 C14 1.380(4) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C15 C16 1.491(3) . ?
C15 C22 1.496(4) . ?
C16 C17 1.382(4) . ?
C16 C21 1.384(4) . ?
C17 C18 1.377(4) . ?
C17 H17 0.9300 . ?
C18 C19 1.371(5) . ?
C18 H18 0.9300 . ?
C19 C20 1.359(5) . ?
C19 H19 0.9300 . ?
C20 C21 1.383(4) . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?
C22 C23 1.371(4) . ?
C22 C27 1.378(4) . ?
C23 C24 1.368(5) . ?
C23 H23 0.9300 . ?
C24 C25 1.358(7) . ?
C24 H24 0.9300 . ?
C25 C26 1.349(7) . ?
C25 H25 0.9300 . ?
C26 C27 1.374(5) . ?
C26 H26 0.9300 . ?
C27 H27 0.9300 . ?
C28 C30 1.506(5) . ?
C28 C31 1.507(5) . ?
C28 C29 1.515(4) . ?
C29 H29A 0.9600 . ?
C29 H29B 0.9600 . ?
C29 H29C 0.9600 . ?
C30 H30A 0.9600 . ?
C30 H30B 0.9600 . ?
C30 H30C 0.9600 . ?
C31 H31A 0.9600 . ?
C31 H31B 0.9600 . ?
C31 H31C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1' S1 N1 124.1(6) . . ?
O1 S1 N1 114.83(16) . . ?
O1' S1 C28 113.0(6) . . ?
O1 S1 C28 107.31(16) . . ?
N1 S1 C28 98.14(12) . . ?
C1 N1 S1 115.48(18) . . ?
C1 N1 H1A 108(3) . . ?
S1 N1 H1A 103(3) . . ?
C15 N2 C2 119.6(2) . . ?
N1 C1 C6 108.6(2) . . ?
N1 C1 C2 110.8(2) . . ?
C6 C1 C2 111.6(2) . . ?
N1 C1 H1 108.6 . . ?
C6 C1 H1 108.6 . . ?
C2 C1 H1 108.6 . . ?
N2 C2 C3 110.1(2) . . ?
N2 C2 C1 106.0(2) . . ?
C3 C2 C1 109.9(2) . . ?
N2 C2 H2 110.2 . . ?
C3 C2 H2 110.2 . . ?
C1 C2 H2 110.2 . . ?
C14 C3 C4 119.6(3) . . ?
C14 C3 C2 120.9(2) . . ?
C4 C3 C2 119.5(2) . . ?
C11 C4 C3 118.6(2) . . ?
C11 C4 C5 121.9(2) . . ?
C3 C4 C5 119.5(2) . . ?
C6 C5 C10 118.6(2) . . ?
C6 C5 C4 119.4(2) . . ?
C10 C5 C4 121.9(2) . . ?
C7 C6 C5 119.4(2) . . ?
C7 C6 C1 120.7(2) . . ?
C5 C6 C1 119.8(2) . . ?
C8 C7 C6 121.6(3) . . ?
C8 C7 H7 119.2 . . ?
C6 C7 H7 119.2 . . ?
C9 C8 C7 117.8(3) . . ?
C9 C8 H8 121.1 . . ?
C7 C8 H8 121.1 . . ?
F1 C9 C10 118.2(3) . . ?
F1 C9 C8 118.8(3) . . ?
C10 C9 C8 123.0(3) . . ?
C9 C10 C5 119.5(3) . . ?
C9 C10 H10 120.2 . . ?
C5 C10 H10 120.2 . . ?
C12 C11 C4 119.6(3) . . ?
C12 C11 H11 120.2 . . ?
C4 C11 H11 120.2 . . ?
C11 C12 F2 118.8(3) . . ?
C11 C12 C13 123.3(3) . . ?
F2 C12 C13 117.9(3) . . ?
C12 C13 C14 117.5(3) . . ?
C12 C13 H13 121.2 . . ?
C14 C13 H13 121.2 . . ?
C3 C14 C13 121.4(3) . . ?
C3 C14 H14 119.3 . . ?
C13 C14 H14 119.3 . . ?
N2 C15 C16 117.6(2) . . ?
N2 C15 C22 125.3(2) . . ?
C16 C15 C22 117.0(2) . . ?
C17 C16 C21 118.6(3) . . ?
C17 C16 C15 119.9(2) . . ?
C21 C16 C15 121.6(3) . . ?
C18 C17 C16 120.5(3) . . ?
C18 C17 H17 119.7 . . ?
C16 C17 H17 119.7 . . ?
C19 C18 C17 120.0(3) . . ?
C19 C18 H18 120.0 . . ?
C17 C18 H18 120.0 . . ?
C20 C19 C18 120.4(3) . . ?
C20 C19 H19 119.8 . . ?
C18 C19 H19 119.8 . . ?
C19 C20 C21 120.0(3) . . ?
C19 C20 H20 120.0 . . ?
C21 C20 H20 120.0 . . ?
C20 C21 C16 120.4(3) . . ?
C20 C21 H21 119.8 . . ?
C16 C21 H21 119.8 . . ?
C23 C22 C27 118.8(3) . . ?
C23 C22 C15 121.5(3) . . ?
C27 C22 C15 119.7(3) . . ?
C24 C23 C22 120.6(4) . . ?
C24 C23 H23 119.7 . . ?
C22 C23 H23 119.7 . . ?
C25 C24 C23 119.9(5) . . ?
C25 C24 H24 120.0 . . ?
C23 C24 H24 120.0 . . ?
C26 C25 C24 120.3(4) . . ?
C26 C25 H25 119.8 . . ?
C24 C25 H25 119.8 . . ?
C25 C26 C27 120.5(5) . . ?
C25 C26 H26 119.8 . . ?
C27 C26 H26 119.8 . . ?
C26 C27 C22 119.8(4) . . ?
C26 C27 H27 120.1 . . ?
C22 C27 H27 120.1 . . ?
C30 C28 C31 113.4(3) . . ?
C30 C28 C29 110.8(3) . . ?
C31 C28 C29 110.1(3) . . ?
C30 C28 S1 107.2(2) . . ?
C31 C28 S1 111.1(2) . . ?
C29 C28 S1 103.9(2) . . ?
C28 C29 H29A 109.5 . . ?
C28 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C28 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C28 C30 H30A 109.5 . . ?
C28 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
C28 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C28 C31 H31A 109.5 . . ?
C28 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
C28 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 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
O1' S1 N1 C1 -53.1(9) . . . . ?
O1 S1 N1 C1 68.5(3) . . . . ?
C28 S1 N1 C1 -178.1(2) . . . . ?
S1 N1 C1 C6 162.13(19) . . . . ?
S1 N1 C1 C2 -75.0(3) . . . . ?
C15 N2 C2 C3 119.1(3) . . . . ?
C15 N2 C2 C1 -122.0(3) . . . . ?
N1 C1 C2 N2 171.0(2) . . . . ?
C6 C1 C2 N2 -68.0(3) . . . . ?
N1 C1 C2 C3 -70.1(3) . . . . ?
C6 C1 C2 C3 51.0(3) . . . . ?
N2 C2 C3 C14 -101.4(3) . . . . ?
C1 C2 C3 C14 142.2(2) . . . . ?
N2 C2 C3 C4 77.4(3) . . . . ?
C1 C2 C3 C4 -39.0(3) . . . . ?
C14 C3 C4 C11 3.0(4) . . . . ?
C2 C3 C4 C11 -175.8(2) . . . . ?
C14 C3 C4 C5 -174.7(2) . . . . ?
C2 C3 C4 C5 6.5(3) . . . . ?
C11 C4 C5 C6 -163.5(2) . . . . ?
C3 C4 C5 C6 14.1(3) . . . . ?
C11 C4 C5 C10 13.8(4) . . . . ?
C3 C4 C5 C10 -168.7(2) . . . . ?
C10 C5 C6 C7 0.6(4) . . . . ?
C4 C5 C6 C7 178.0(2) . . . . ?
C10 C5 C6 C1 -176.2(2) . . . . ?
C4 C5 C6 C1 1.1(3) . . . . ?
N1 C1 C6 C7 -88.8(3) . . . . ?
C2 C1 C6 C7 148.8(3) . . . . ?
N1 C1 C6 C5 88.1(3) . . . . ?
C2 C1 C6 C5 -34.3(3) . . . . ?
C5 C6 C7 C8 -0.7(4) . . . . ?
C1 C6 C7 C8 176.2(3) . . . . ?
C6 C7 C8 C9 -0.1(5) . . . . ?
C7 C8 C9 F1 -178.7(3) . . . . ?
C7 C8 C9 C10 0.9(5) . . . . ?
F1 C9 C10 C5 178.7(2) . . . . ?
C8 C9 C10 C5 -1.0(4) . . . . ?
C6 C5 C10 C9 0.1(4) . . . . ?
C4 C5 C10 C9 -177.1(2) . . . . ?
C3 C4 C11 C12 -1.6(4) . . . . ?
C5 C4 C11 C12 176.0(2) . . . . ?
C4 C11 C12 F2 179.9(2) . . . . ?
C4 C11 C12 C13 -0.8(5) . . . . ?
C11 C12 C13 C14 1.7(5) . . . . ?
F2 C12 C13 C14 -179.0(3) . . . . ?
C4 C3 C14 C13 -2.1(4) . . . . ?
C2 C3 C14 C13 176.7(3) . . . . ?
C12 C13 C14 C3 -0.2(4) . . . . ?
C2 N2 C15 C16 175.3(2) . . . . ?
C2 N2 C15 C22 -4.1(4) . . . . ?
N2 C15 C16 C17 -26.4(4) . . . . ?
C22 C15 C16 C17 153.1(3) . . . . ?
N2 C15 C16 C21 153.3(3) . . . . ?
C22 C15 C16 C21 -27.2(4) . . . . ?
C21 C16 C17 C18 -1.6(4) . . . . ?
C15 C16 C17 C18 178.1(2) . . . . ?
C16 C17 C18 C19 1.3(5) . . . . ?
C17 C18 C19 C20 -0.4(5) . . . . ?
C18 C19 C20 C21 0.0(5) . . . . ?
C19 C20 C21 C16 -0.4(5) . . . . ?
C17 C16 C21 C20 1.2(4) . . . . ?
C15 C16 C21 C20 -178.5(3) . . . . ?
N2 C15 C22 C23 -75.6(4) . . . . ?
C16 C15 C22 C23 104.9(3) . . . . ?
N2 C15 C22 C27 103.9(3) . . . . ?
C16 C15 C22 C27 -75.5(3) . . . . ?
C27 C22 C23 C24 -1.4(5) . . . . ?
C15 C22 C23 C24 178.1(3) . . . . ?
C22 C23 C24 C25 0.1(6) . . . . ?
C23 C24 C25 C26 0.9(7) . . . . ?
C24 C25 C26 C27 -0.6(7) . . . . ?
C25 C26 C27 C22 -0.7(6) . . . . ?
C23 C22 C27 C26 1.7(5) . . . . ?
C15 C22 C27 C26 -177.8(3) . . . . ?
O1' S1 C28 C30 -64.6(7) . . . . ?
O1 S1 C28 C30 -172.7(3) . . . . ?
N1 S1 C28 C30 68.0(3) . . . . ?
O1' S1 C28 C31 171.1(7) . . . . ?
O1 S1 C28 C31 62.9(3) . . . . ?
N1 S1 C28 C31 -56.3(3) . . . . ?
O1' S1 C28 C29 52.7(7) . . . . ?
O1 S1 C28 C29 -55.4(3) . . . . ?
N1 S1 C28 C29 -174.7(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C13 H13 O1 0.93 2.26 3.178(4) 170.6 2_655
C2 H2 O1 0.98 2.45 3.191(4) 131.6 .
C13 H13 O1 0.93 2.26 3.178(4) 170.6 2_655
C2 H2 O1 0.98 2.45 3.191(4) 131.6 .
C2 H2 O1 0.98 2.45 3.191(4) 131.6 .
C13 H13 O1 0.93 2.26 3.178(4) 170.6 2_655

_refine_diff_density_max         0.499
_refine_diff_density_min         -0.331
_refine_diff_density_rms         0.041

_shelxl_version_number           2013-4

