# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_ans-687
_database_code_depnum_ccdc_archive 'CCDC 2064004'
loop_
_audit_author_name
_audit_author_address
'Ekaterina S. Mescheryakova'
;Institute Petrochemistry and Catalysis UFRC RAS
Russia
;
_audit_update_record             
;
2021-02-20 deposited with the CCDC.	2021-05-17 downloaded from the CCDC.
;
_audit_creation_date             2020-12-23
_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         'C24 H22 F2 N4 S4, 4(C2 H6 O S)'
_chemical_formula_sum            'C32 H46 F2 N4 O4 S8'
_chemical_formula_weight         845.21
_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      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                   8.1311(4)
_cell_length_b                   11.9456(7)
_cell_length_c                   12.1000(12)
_cell_angle_alpha                103.820(7)
_cell_angle_beta                 109.146(6)
_cell_angle_gamma                93.699(4)
_cell_volume                     1064.98(14)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    2283
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.0900
_cell_measurement_theta_min      2.6700
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.466
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.94759
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.318
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prizm
_exptl_crystal_F_000             444
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0209
_diffrn_reflns_av_unetI/netI     0.0536
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.849
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8840
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.849
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.199
_diffrn_reflns_theta_min         2.186
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1709
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega    7.00   43.00   1.0000   17.7500
omega____ theta____ kappa____ phi______ frames
    -       16.9480  -19.0000   30.0000 36

#__ type_ start__ end____ width___ exp.time_
  2 omega   55.00   87.00   1.0000   17.7500
omega____ theta____ kappa____ phi______ frames
    -       16.9480   19.0000  -60.0000 32

#__ type_ start__ end____ width___ exp.time_
  3 omega    4.00   74.00   1.0000   17.7500
omega____ theta____ kappa____ phi______ frames
    -       16.9480   38.0000 -150.0000 70

#__ type_ start__ end____ width___ exp.time_
  4 omega   -7.00   21.00   1.0000   17.7500
omega____ theta____ kappa____ phi______ frames
    -       16.9480   19.0000  -60.0000 28

#__ type_ start__ end____ width___ exp.time_
  5 omega  -54.00   -6.00   1.0000   17.7500
omega____ theta____ kappa____ phi______ frames
    -       16.9480  -19.0000   30.0000 48

#__ type_ start__ end____ width___ exp.time_
  6 omega  -23.00   20.00   1.0000   17.7500
omega____ theta____ kappa____ phi______ frames
    -      -16.2449  -99.0000   30.0000 43

#__ type_ start__ end____ width___ exp.time_
  7 omega  -20.00   49.00   1.0000   17.7500
omega____ theta____ kappa____ phi______ frames
    -       16.9480  -99.0000    0.0000 69

#__ type_ start__ end____ width___ exp.time_
  8 omega  -23.00   17.00   1.0000   17.7500
omega____ theta____ kappa____ phi______ frames
    -      -16.2449  -99.0000 -150.0000 40
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0017184000
_diffrn_orient_matrix_UB_12      -0.0360820000
_diffrn_orient_matrix_UB_13      0.0385529000
_diffrn_orient_matrix_UB_21      -0.0292974000
_diffrn_orient_matrix_UB_22      -0.0498175000
_diffrn_orient_matrix_UB_23      -0.0511756000
_diffrn_orient_matrix_UB_31      0.0887591000
_diffrn_orient_matrix_UB_32      -0.0069894000
_diffrn_orient_matrix_UB_33      0.0079543000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3195
_reflns_number_total             4905
_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.338
_refine_diff_density_min         -0.370
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.877
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     250
_refine_ls_number_reflns         4905
_refine_ls_number_restraints     21
_refine_ls_R_factor_all          0.0815
_refine_ls_R_factor_gt           0.0477
_refine_ls_restrained_S_all      0.875
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1315
_refine_ls_wR_factor_ref         0.1572
_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,H) groups
 At 1.5 times of:
  All C(H,H,H,H,H,H) groups
2. Rigid body (RIGU) restrains
 S3A, S3, O2, C16, C17
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
3. Others
 Sof(S3A)=1-FVAR(1)
 Sof(S3)=FVAR(1)
 Fixed Sof: S2(0.6154) H14A(0.6154) H14B(0.6154) H14C(0.6154) H14D(0.3846)
 H14E(0.3846) H14F(0.3846) H16A(0.94915) H16B(0.94915) H16C(0.94915)
 H16D(0.05085) H16E(0.05085) H16F(0.05085) H15A(0.6154) H15B(0.6154)
 H15C(0.6154) H15D(0.3846) H15E(0.3846) H15F(0.3846) H17A(0.94915)
 H17B(0.94915) H17C(0.94915) H17D(0.05085) H17E(0.05085) H17F(0.05085)
 S2A(0.3846)
4.a Rotating group:
 N2(H2A,H2B)
4.b Ternary CH refined with riding coordinates:
 C4(H4)
4.c Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C6(H6A,H6B)
4.d Aromatic/amide H refined with riding coordinates:
 C9(H9), C13(H13), C10(H10), C12(H12)
4.e Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C14(H14D,H14E,H14F), C16(H16A,H16B,H16C), C16(H16D,H16E,
 H16F), C15(H15A,H15B,H15C), C15(H15D,H15E,H15F), C17(H17A,H17B,H17C), C17(H17D,
 H17E,H17F)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S5 S 0.43401(9) 0.28860(5) 0.47856(7) 0.0486(2) Uani 1 1 d . . . . .
S1 S 0.76547(8) -0.05590(6) 0.34727(7) 0.0499(2) Uani 1 1 d . . . . .
S3 S 1.12785(11) 0.66439(7) 0.10082(8) 0.0698(4) Uani 0.949(3) 1 d . U P A 1
S2 S 0.98129(14) 0.13438(11) 0.10751(12) 0.0584(3) Uani 0.6154 1 d . . P B 1
C8 C 0.5438(3) 0.31566(19) 0.2940(2) 0.0376(5) Uani 1 1 d . . . . .
C7 C 0.6744(3) -0.1845(2) 0.3744(3) 0.0460(6) Uani 1 1 d . . . . .
H7A H 0.563734 -0.219448 0.308525 0.055 Uiso 1 1 calc R . . . .
H7B H 0.754819 -0.241124 0.375323 0.055 Uiso 1 1 calc R . . . .
C4 C 0.4894(3) 0.22227(19) 0.3448(2) 0.0370(5) Uani 1 1 d . . . . .
H4 H 0.381384 0.174514 0.282538 0.044 Uiso 1 1 calc R . . . .
C3 C 0.6240(3) 0.1418(2) 0.3712(2) 0.0373(5) Uani 1 1 d . . . . .
C2 C 0.5879(3) 0.0248(2) 0.3224(2) 0.0379(5) Uani 1 1 d . . . . .
C6 C 0.3564(4) 0.1557(2) 0.5072(3) 0.0509(6) Uani 1 1 d . . . . .
H6A H 0.247554 0.116333 0.441578 0.061 Uiso 1 1 calc R . . . .
H6B H 0.443230 0.103410 0.509866 0.061 Uiso 1 1 calc R . . . .
N2 N 0.4276(3) -0.03503(18) 0.2498(2) 0.0558(6) Uani 1 1 d . . . . .
H2A H 0.417242 -0.102996 0.261567 0.067 Uiso 1 1 d GR . . . .
H2B H 0.348384 0.002270 0.267350 0.067 Uiso 1 1 d GR . . . .
C9 C 0.6630(3) 0.4156(2) 0.3658(3) 0.0495(6) Uani 1 1 d . . . . .
H9 H 0.705546 0.429134 0.449882 0.059 Uiso 1 1 calc R . . . .
F1 F 0.7122(3) 0.55134(18) 0.1415(2) 0.0960(7) Uani 1 1 d . . . . .
C3' C 0.7951(3) 0.1965(2) 0.4552(3) 0.0485(6) Uani 1 1 d . . . . .
C13 C 0.4804(3) 0.2991(2) 0.1693(3) 0.0493(6) Uani 1 1 d . . . . .
H13 H 0.398489 0.233418 0.119469 0.059 Uiso 1 1 calc R . . . .
C11 C 0.6551(4) 0.4738(3) 0.1927(3) 0.0605(8) Uani 1 1 d . . . . .
O1 O 1.1013(2) 0.0625(2) 0.1670(2) 0.0871(8) Uani 1 1 d . . . . .
O2 O 1.2973(3) 0.72594(19) 0.1083(2) 0.0804(7) Uani 1 1 d . U . . .
C10 C 0.7199(4) 0.4954(2) 0.3153(3) 0.0577(8) Uani 1 1 d . . . . .
H10 H 0.800323 0.562025 0.364009 0.069 Uiso 1 1 calc R . . . .
C12 C 0.5363(4) 0.3780(3) 0.1173(3) 0.0627(8) Uani 1 1 d . . . . .
H12 H 0.494131 0.366190 0.033391 0.075 Uiso 1 1 calc R . . . .
C14 C 0.9837(5) 0.2586(3) 0.2196(4) 0.0950(13) Uani 1 1 d . . . . .
H14A H 0.956881 0.235447 0.283298 0.142 Uiso 0.6154 1 calc GR . P B 1
H14B H 0.897160 0.303268 0.184378 0.142 Uiso 0.6154 1 calc GR . P B 1
H14C H 1.098302 0.305325 0.252769 0.142 Uiso 0.6154 1 calc GR . P B 1
H14D H 1.085994 0.298219 0.288981 0.142 Uiso 0.3846 1 calc GR . P B 2
H14E H 0.880720 0.287337 0.230264 0.142 Uiso 0.3846 1 calc GR . P B 2
H14F H 0.995714 0.272597 0.147559 0.142 Uiso 0.3846 1 calc GR . P B 2
C16 C 1.0354(6) 0.7677(4) 0.1842(5) 0.1105(16) Uani 1 1 d . U . . .
H16A H 1.112558 0.793748 0.267791 0.166 Uiso 0.9491 1 calc GR . P A 1
H16B H 0.922927 0.732269 0.179403 0.166 Uiso 0.9491 1 calc GR . P A 1
H16C H 1.020391 0.833137 0.150708 0.166 Uiso 0.9491 1 calc GR . P A 1
H16D H 1.053914 0.849966 0.222709 0.166 Uiso 0.0508 1 calc GR . P A 2
H16E H 0.958695 0.727752 0.213038 0.166 Uiso 0.0508 1 calc GR . P A 2
H16F H 0.982451 0.753600 0.097639 0.166 Uiso 0.0508 1 calc GR . P A 2
C15 C 0.7648(3) 0.0644(3) 0.0729(3) 0.0788(10) Uani 1 1 d . . . . .
H15A H 0.740627 -0.007107 0.009651 0.118 Uiso 0.6154 1 calc GR . P B 1
H15B H 0.682015 0.114667 0.045950 0.118 Uiso 0.6154 1 calc GR . P B 1
H15C H 0.754403 0.047752 0.144311 0.118 Uiso 0.6154 1 calc GR . P B 1
H15D H 0.774996 0.098692 0.010834 0.118 Uiso 0.3846 1 calc GR . P B 2
H15E H 0.665845 0.087642 0.094175 0.118 Uiso 0.3846 1 calc GR . P B 2
H15F H 0.748002 -0.019064 0.043077 0.118 Uiso 0.3846 1 calc GR . P B 2
C17 C 1.1776(5) 0.5736(3) 0.2001(4) 0.0940(12) Uani 1 1 d . U . . .
H17A H 1.222724 0.507373 0.164814 0.141 Uiso 0.9491 1 calc GR . P A 1
H17B H 1.072541 0.547365 0.212475 0.141 Uiso 0.9491 1 calc GR . P A 1
H17C H 1.264461 0.616850 0.276870 0.141 Uiso 0.9491 1 calc GR . P A 1
H17D H 1.160360 0.530772 0.118189 0.141 Uiso 0.0508 1 calc GR . P A 2
H17E H 1.077258 0.551926 0.220007 0.141 Uiso 0.0508 1 calc GR . P A 2
H17F H 1.281476 0.555915 0.255073 0.141 Uiso 0.0508 1 calc GR . P A 2
N1 N 0.9259(3) 0.2494(2) 0.5227(3) 0.0758(9) Uani 1 1 d . . . . .
S2A S 0.9636(2) 0.11333(17) 0.20572(17) 0.0533(4) Uani 0.3846 1 d . . P B 2
S3A S 1.203(3) 0.7251(16) 0.213(2) 0.088(8) Uani 0.051(3) 1 d . U 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
S5 C4 1.834(3) . ?
S5 C6 1.821(3) . ?
S1 C7 1.808(3) . ?
S1 C2 1.771(2) . ?
S3 O2 1.484(2) . ?
S3 C16 1.769(4) . ?
S3 C17 1.773(4) . ?
S2 O1 1.466(2) . ?
S2 C14 1.750(4) . ?
S2 C15 1.769(3) . ?
C8 C4 1.503(3) . ?
C8 C9 1.386(3) . ?
C8 C13 1.384(4) . ?
C7 C6 1.499(4) 2_656 ?
C4 C3 1.509(3) . ?
C3 C2 1.352(3) . ?
C3 C3' 1.426(3) . ?
C2 N2 1.345(3) . ?
C9 C10 1.379(4) . ?
F1 C11 1.365(3) . ?
C3' N1 1.138(3) . ?
C13 C12 1.382(4) . ?
C11 C10 1.353(4) . ?
C11 C12 1.362(4) . ?
O1 S2A 1.462(3) . ?
O2 S3A 1.69(2) . ?
C14 S2A 1.695(4) . ?
C16 S3A 1.45(2) . ?
C15 S2A 1.806(3) . ?
C17 S3A 1.771(19) . ?

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
C6 S5 C4 98.74(12) . . ?
C2 S1 C7 102.82(10) . . ?
O2 S3 C16 106.57(17) . . ?
O2 S3 C17 107.61(17) . . ?
C16 S3 C17 98.2(2) . . ?
O1 S2 C14 107.86(18) . . ?
O1 S2 C15 106.55(18) . . ?
C14 S2 C15 98.7(2) . . ?
C9 C8 C4 123.0(2) . . ?
C13 C8 C4 119.0(2) . . ?
C13 C8 C9 117.9(2) . . ?
C6 C7 S1 111.46(18) 2_656 . ?
C8 C4 S5 109.96(15) . . ?
C8 C4 C3 113.09(18) . . ?
C3 C4 S5 112.13(16) . . ?
C2 C3 C4 123.58(18) . . ?
C2 C3 C3' 120.74(19) . . ?
C3' C3 C4 115.7(2) . . ?
C3 C2 S1 118.19(16) . . ?
N2 C2 S1 116.90(17) . . ?
N2 C2 C3 124.79(19) . . ?
C7 C6 S5 110.04(18) 2_656 . ?
C10 C9 C8 121.5(3) . . ?
N1 C3' C3 173.9(3) . . ?
C12 C13 C8 121.3(2) . . ?
C10 C11 F1 118.6(3) . . ?
C10 C11 C12 123.3(3) . . ?
C12 C11 F1 118.1(3) . . ?
C11 C10 C9 118.0(3) . . ?
C11 C12 C13 118.0(3) . . ?
O1 S2A C14 110.9(2) . . ?
O1 S2A C15 104.90(18) . . ?
C14 S2A C15 99.34(19) . . ?
O2 S3A C17 99.2(9) . . ?
C16 S3A O2 112.7(15) . . ?
C16 S3A C17 112.1(12) . . ?


####################################################################### 
# 
# 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_ans-257
_database_code_depnum_ccdc_archive 'CCDC 2064003'
loop_
_audit_author_name
_audit_author_address
'Ekaterina S. Mescheryakova'
;Institute Petrochemistry and Catalysis UFRC RAS
Russia
;
_audit_update_record             
;
2021-02-20 deposited with the CCDC.	2021-05-17 downloaded from the CCDC.
;
_audit_creation_date             2020-12-23
_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         'C10 H5 F N2'
_chemical_formula_sum            'C10 H5 F N2'
_chemical_formula_weight         172.16
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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                   6.9541(7)
_cell_length_b                   7.3664(5)
_cell_length_c                   9.1492(10)
_cell_angle_alpha                107.194(8)
_cell_angle_beta                 99.036(9)
_cell_angle_gamma                102.848(8)
_cell_volume                     423.86(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1411
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      31.0147
_cell_measurement_theta_min      2.3951
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91595
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.349
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prizm
_exptl_crystal_F_000             176.0
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0132
_diffrn_reflns_av_unetI/netI     0.0236
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.879
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            3675
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.879
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.084
_diffrn_reflns_theta_min         2.400
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.1709
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -92.00  -12.00   1.0000    5.2300
omega____ theta____ kappa____ phi______ frames
    -      -23.6098  -57.0000  -30.0000 80

#__ type_ start__ end____ width___ exp.time_
  2 omega  -97.00   13.00   1.0000    5.2300
omega____ theta____ kappa____ phi______ frames
    -      -23.6098  -19.0000   30.0000 110

#__ type_ start__ end____ width___ exp.time_
  3 omega  -71.00  -33.00   1.0000    5.2300
omega____ theta____ kappa____ phi______ frames
    -      -23.6098  115.0000   58.0000 38

#__ type_ start__ end____ width___ exp.time_
  4 omega  -42.00   36.00   1.0000    5.2300
omega____ theta____ kappa____ phi______ frames
    -      -23.6098   57.0000 -150.0000 78

#__ type_ start__ end____ width___ exp.time_
  5 omega    5.00   76.00   1.0000    5.2300
omega____ theta____ kappa____ phi______ frames
    -       24.5473 -115.0000  -58.0000 71
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0428398000
_diffrn_orient_matrix_UB_12      0.0182415000
_diffrn_orient_matrix_UB_13      0.0804229000
_diffrn_orient_matrix_UB_21      -0.0955171000
_diffrn_orient_matrix_UB_22      0.0020252000
_diffrn_orient_matrix_UB_23      0.0174240000
_diffrn_orient_matrix_UB_31      -0.0254958000
_diffrn_orient_matrix_UB_32      -0.1035371000
_diffrn_orient_matrix_UB_33      -0.0146284000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1863
_reflns_number_total             2396
_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.211
_refine_diff_density_min         -0.184
_refine_diff_density_rms         0.034
_refine_ls_extinction_coef       0.17(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     139
_refine_ls_number_reflns         2396
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0605
_refine_ls_R_factor_gt           0.0460
_refine_ls_restrained_S_all      1.049
_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)+(0.0623P)²+0.0418P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1190
_refine_ls_wR_factor_ref         0.1335
_refine_special_details          ?
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.45413(17) 0.75582(15) 0.51296(12) 0.0371(3) Uani 1 1 d . . . . .
C2 C 0.51128(17) 0.89025(16) 0.67488(13) 0.0383(3) Uani 1 1 d . . . . .
C3 C 0.69530(17) 0.99448(16) 0.77126(12) 0.0379(3) Uani 1 1 d . . . . .
C4 C 0.5893(2) 0.71981(19) 0.41732(15) 0.0462(3) Uani 1 1 d . . . . .
C5 C 0.70847(18) 1.11995(18) 0.92842(14) 0.0460(3) Uani 1 1 d . . . . .
C6 C 0.88627(18) 0.99413(18) 0.73218(14) 0.0470(3) Uani 1 1 d . . . . .
F7 F 0.24899(18) 0.36543(14) 0.05995(10) 0.0871(4) Uani 1 1 d . . . . .
N8 N 0.7196(2) 1.22080(19) 1.05250(14) 0.0655(4) Uani 1 1 d . . . . .
C9 C 0.5198(2) 0.5884(2) 0.26389(16) 0.0562(4) Uani 1 1 d . . . . .
C10 C 0.2480(2) 0.65921(19) 0.44985(15) 0.0491(3) Uani 1 1 d . . . . .
N11 N 1.0405(2) 0.9958(2) 0.70443(17) 0.0743(4) Uani 1 1 d . . . . .
C12 C 0.1775(2) 0.5278(2) 0.29733(18) 0.0592(4) Uani 1 1 d . . . . .
C13 C 0.3156(3) 0.49484(19) 0.20890(15) 0.0563(4) Uani 1 1 d . . . . .
H2 H 0.399(2) 0.902(2) 0.7178(17) 0.046(3) Uiso 1 1 d . . . . .
H10 H 0.153(3) 0.684(2) 0.515(2) 0.065(4) Uiso 1 1 d . . . . .
H9 H 0.609(3) 0.559(3) 0.194(2) 0.077(5) Uiso 1 1 d . . . . .
H12 H 0.037(3) 0.462(3) 0.253(2) 0.087(6) Uiso 1 1 d . . . . .
H4 H 0.735(3) 0.784(2) 0.4552(18) 0.059(4) 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
C1 C2 1.4512(14) . ?
C1 C4 1.3970(16) . ?
C1 C10 1.3923(16) . ?
C2 C3 1.3465(16) . ?
C3 C5 1.4371(15) . ?
C3 C6 1.4289(16) . ?
C4 C9 1.3844(18) . ?
C5 N8 1.1380(16) . ?
C6 N11 1.1384(18) . ?
F7 C13 1.3482(14) . ?
C9 C13 1.371(2) . ?
C10 C12 1.3785(18) . ?
C12 C13 1.366(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C4 C1 C2 124.93(11) . . ?
C10 C1 C2 116.48(10) . . ?
C10 C1 C4 118.59(11) . . ?
C3 C2 C1 130.87(10) . . ?
C2 C3 C5 119.31(10) . . ?
C2 C3 C6 125.82(10) . . ?
C6 C3 C5 114.87(10) . . ?
C9 C4 C1 120.60(13) . . ?
N8 C5 C3 179.37(14) . . ?
N11 C6 C3 178.51(14) . . ?
C13 C9 C4 118.28(13) . . ?
C12 C10 C1 121.17(13) . . ?
C13 C12 C10 118.21(14) . . ?
F7 C13 C9 118.04(14) . . ?
F7 C13 C12 118.83(14) . . ?
C12 C13 C9 123.13(12) . . ?


####################################################################### 
# 
# 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_ans-763
_database_code_depnum_ccdc_archive 'CCDC 2064005'
loop_
_audit_author_name
_audit_author_address
'Ekaterina S. Mescheryakova'
;Institute Petrochemistry and Catalysis UFRC RAS
Russia
;
_audit_update_record             
;
2021-02-20 deposited with the CCDC.	2021-05-17 downloaded from the CCDC.
;
_audit_creation_date             2020-12-23
_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         'C24 H22 Cl2 N4 S4, 6(C2 H6 O S)'
_chemical_formula_sum            'C36 H58 Cl2 N4 O6 S10'
_chemical_formula_weight         1034.36
_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'
Cl Cl 0.1484 0.1585 '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           61
_space_group_name_H-M_alt        'P b c a'
_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'
'-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                   18.600(2)
_cell_length_b                   9.7722(10)
_cell_length_c                   28.091(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     5105.9(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1892
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.9470
_cell_measurement_theta_min      2.4800
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.580
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.53548
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.346
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plank
_exptl_crystal_F_000             2176
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1149
_diffrn_reflns_av_unetI/netI     0.1509
_diffrn_reflns_Laue_measured_fraction_full 0.970
_diffrn_reflns_Laue_measured_fraction_max 0.851
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            15833
_diffrn_reflns_point_group_measured_fraction_full 0.970
_diffrn_reflns_point_group_measured_fraction_max 0.851
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.390
_diffrn_reflns_theta_min         2.190
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1709
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -18.25   23.00   0.7500   46.0600
omega____ theta____ kappa____ phi______ frames
    -      -16.2449  -99.0000   60.0000 55

#__ type_ start__ end____ width___ exp.time_
  2 omega    2.00   52.25   0.7500   46.0600
omega____ theta____ kappa____ phi______ frames
    -       16.9480   57.0000 -120.0000 67

#__ type_ start__ end____ width___ exp.time_
  3 omega  -40.00   30.50   0.7500   46.0600
omega____ theta____ kappa____ phi______ frames
    -       16.9480  -57.0000  -90.0000 94
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0193217000
_diffrn_orient_matrix_UB_12      -0.0206468000
_diffrn_orient_matrix_UB_13      0.0205503000
_diffrn_orient_matrix_UB_21      -0.0326632000
_diffrn_orient_matrix_UB_22      -0.0200831000
_diffrn_orient_matrix_UB_23      0.0110984000
_diffrn_orient_matrix_UB_31      0.0038536000
_diffrn_orient_matrix_UB_32      -0.0665871000
_diffrn_orient_matrix_UB_33      -0.0096524000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1864
_reflns_number_total             5993
_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.436
_refine_diff_density_min         -0.252
_refine_diff_density_rms         0.072
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.901
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     295
_refine_ls_number_reflns         5993
_refine_ls_number_restraints     145
_refine_ls_R_factor_all          0.2347
_refine_ls_R_factor_gt           0.0998
_refine_ls_restrained_S_all      0.908
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1129P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2187
_refine_ls_wR_factor_ref         0.2941
_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,H) groups
 At 1.5 times of:
  All C(H,H,H,H,H,H) groups
2. Restrained distances
 O2-S3 \\sim O2-S3A
 with sigma of 0.02
3. Rigid bond restraints
 S2, O1, C14, C15, S2A
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 O2
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 S3, O2, S3A, C16, C17
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
S2A \\sim S2 \\sim O1 \\sim C14 \\sim C15: within 2A with sigma of 0.04 and
sigma for terminal atoms of 0.08
O2: within 2A with sigma of 0.04 and sigma for terminal atoms of 0.08
S3 \\sim O2 \\sim S3A \\sim C16 \\sim C17: within 2A with sigma of 0.04 and
sigma for terminal atoms of 0.08
5. Rigid body (RIGU) restrains
 S2A, S2, O1, C14, C15
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 O2
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 S3A, O2, S3, C16, C17
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
6. Others
 Fixed Sof: S2(0.91555) S4(0.5994) H19A(0.5994) H19B(0.5994) H19C(0.5994)
 H19D(0.4006) H19E(0.4006) H19F(0.4006) H14A(0.91555) H14B(0.91555)
 H14C(0.91555) H14D(0.08445) H14E(0.08445) H14F(0.08445) H18A(0.5994)
 H18B(0.5994) H18C(0.5994) H18D(0.4006) H18E(0.4006) H18F(0.4006) H15A(0.91555)
 H15B(0.91555) H15C(0.91555) H15D(0.08445) H15E(0.08445) H15F(0.08445)
 S4A(0.4006) S2A(0.08445) S3(0.53652) S3A(0.46348) H16A(0.53652) H16B(0.53652)
 H16C(0.53652) H16D(0.46348) H16E(0.46348) H16F(0.46348) H17A(0.53652)
 H17B(0.53652) H17C(0.53652) H17D(0.46348) H17E(0.46348) H17F(0.46348)
7.a Ternary CH refined with riding coordinates:
 C4(H4)
7.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C6(H6A,H6B)
7.c Aromatic/amide H refined with riding coordinates:
 C12(H12), C9(H9), C13(H13), C10(H10)
7.d X=CH2 refined with riding coordinates:
 N1(H1A,H1B)
7.e Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C19(H19D,H19E,H19F), C14(H14A,H14B,H14C), C14(H14D,H14E,
 H14F), C18(H18A,H18B,H18C), C18(H18D,H18E,H18F), C15(H15A,H15B,H15C), C15(H15D,
 H15E,H15F), C16(H16A,H16B,H16C), C16(H16D,H16E,H16F), C17(H17A,H17B,H17C),
 C17(H17D,H17E,H17F)
;
_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 0.55109(9) 0.79756(16) 0.54899(6) 0.0727(5) Uani 1 1 d . . . . .
S5 S 0.47550(11) 0.29942(16) 0.60078(6) 0.0764(6) Uani 1 1 d . . . . .
S2 S 0.30098(11) 0.9119(2) 0.46692(9) 0.0908(7) Uani 0.9155 1 d . U P A 1
Cl1 Cl 0.49508(12) 0.4483(2) 0.83524(7) 0.1107(8) Uani 1 1 d . . . . .
S4 S 0.2451(3) 0.7075(5) 0.78503(18) 0.1128(13) Uani 0.5994 1 d . . P B 1
O1 O 0.3613(2) 0.9106(5) 0.50091(17) 0.0938(14) Uani 1 1 d . U . . .
N1 N 0.4222(3) 0.6860(5) 0.55594(19) 0.0803(16) Uani 1 1 d . . . . .
H1A H 0.390460 0.630014 0.566672 0.096 Uiso 1 1 calc R . . . .
H1B H 0.409776 0.750522 0.536826 0.096 Uiso 1 1 calc R . . . .
C3 C 0.5150(3) 0.5740(5) 0.59886(19) 0.0539(14) Uani 1 1 d . . . . .
C8 C 0.4767(3) 0.4685(5) 0.6766(2) 0.0586(15) Uani 1 1 d . . . . .
C4 C 0.4671(3) 0.4730(5) 0.6235(2) 0.0592(15) Uani 1 1 d . . . . .
H4 H 0.417456 0.502007 0.617505 0.071 Uiso 1 1 calc R . . . .
C2 C 0.4905(3) 0.6728(6) 0.5689(2) 0.0610(15) Uani 1 1 d . . . . .
C7 C 0.4677(3) 0.1938(5) 0.5128(2) 0.0638(15) Uani 1 1 d . . . . .
H7A H 0.437297 0.124013 0.526820 0.077 Uiso 1 1 calc R . . . .
H7B H 0.517215 0.164603 0.516830 0.077 Uiso 1 1 calc R . . . .
C11 C 0.4891(4) 0.4595(6) 0.7732(2) 0.0660(17) Uani 1 1 d . . . . .
C6 C 0.4575(3) 0.3214(6) 0.53945(19) 0.0674(16) Uani 1 1 d . . . . .
H6A H 0.408309 0.352529 0.535429 0.081 Uiso 1 1 calc R . . . .
H6B H 0.489107 0.391225 0.526686 0.081 Uiso 1 1 calc R . . . .
C12 C 0.5373(3) 0.3919(6) 0.7472(2) 0.0678(16) Uani 1 1 d . . . . .
H12 H 0.574372 0.344227 0.761978 0.081 Uiso 1 1 calc R . . . .
C9 C 0.4298(3) 0.5387(6) 0.7051(2) 0.0687(16) Uani 1 1 d . . . . .
H9 H 0.393157 0.589802 0.691304 0.082 Uiso 1 1 calc R . . . .
C13 C 0.5316(4) 0.3931(6) 0.6981(2) 0.0723(17) Uani 1 1 d . . . . .
H13 H 0.564155 0.344307 0.679517 0.087 Uiso 1 1 calc R . . . .
C3' C 0.5900(4) 0.5597(6) 0.6066(2) 0.0713(17) Uani 1 1 d . . . . .
C10 C 0.4359(4) 0.5349(7) 0.7535(3) 0.0757(18) Uani 1 1 d . . . . .
H10 H 0.403989 0.583328 0.772616 0.091 Uiso 1 1 calc R . . . .
N2 N 0.6484(3) 0.5424(8) 0.6140(3) 0.114(2) Uani 1 1 d . . . . .
O3 O 0.2903(4) 0.7449(11) 0.7477(5) 0.224(5) Uani 1 1 d . . . . .
C19 C 0.2181(6) 0.8434(11) 0.8182(5) 0.157(4) Uani 1 1 d . . . . .
H19A H 0.256103 0.869891 0.839347 0.235 Uiso 0.5994 1 calc GR . P B 1
H19B H 0.176379 0.818557 0.836334 0.235 Uiso 0.5994 1 calc GR . P B 1
H19C H 0.206521 0.918472 0.797502 0.235 Uiso 0.5994 1 calc GR . P B 1
H19D H 0.178095 0.904381 0.822137 0.235 Uiso 0.4006 1 calc GR . P B 2
H19E H 0.261478 0.888302 0.828062 0.235 Uiso 0.4006 1 calc GR . P B 2
H19F H 0.210731 0.762907 0.837148 0.235 Uiso 0.4006 1 calc GR . P B 2
C14 C 0.3328(6) 0.8815(12) 0.4108(3) 0.150(4) Uani 1 1 d . U . . .
H14A H 0.374766 0.824545 0.412636 0.225 Uiso 0.9155 1 calc GR . P A 1
H14B H 0.345099 0.966819 0.395935 0.225 Uiso 0.9155 1 calc GR . P A 1
H14C H 0.296462 0.836198 0.392391 0.225 Uiso 0.9155 1 calc GR . P A 1
H14D H 0.352625 0.971147 0.415735 0.225 Uiso 0.0844 1 calc GR . P A 2
H14E H 0.285277 0.889604 0.397812 0.225 Uiso 0.0844 1 calc GR . P A 2
H14F H 0.362731 0.831535 0.389075 0.225 Uiso 0.0844 1 calc GR . P A 2
C18 C 0.1592(5) 0.6762(10) 0.7592(4) 0.151(4) Uani 1 1 d . . . . .
H18A H 0.123081 0.724996 0.776780 0.226 Uiso 0.5994 1 calc GR . P B 1
H18B H 0.148999 0.579971 0.760208 0.226 Uiso 0.5994 1 calc GR . P B 1
H18C H 0.159191 0.706889 0.726750 0.226 Uiso 0.5994 1 calc GR . P B 1
H18D H 0.160644 0.628210 0.729420 0.226 Uiso 0.4006 1 calc GR . P B 2
H18E H 0.113110 0.719182 0.762921 0.226 Uiso 0.4006 1 calc GR . P B 2
H18F H 0.166835 0.612799 0.784817 0.226 Uiso 0.4006 1 calc GR . P B 2
C15 C 0.2534(6) 0.7679(12) 0.4773(5) 0.183(5) Uani 1 1 d . U . . .
H15A H 0.280858 0.689749 0.467398 0.274 Uiso 0.9155 1 calc GR . P A 1
H15B H 0.209138 0.771067 0.459711 0.274 Uiso 0.9155 1 calc GR . P A 1
H15C H 0.243006 0.760865 0.510690 0.274 Uiso 0.9155 1 calc GR . P A 1
H15D H 0.249470 0.768275 0.511375 0.274 Uiso 0.0844 1 calc GR . P A 2
H15E H 0.239705 0.679599 0.465322 0.274 Uiso 0.0844 1 calc GR . P A 2
H15F H 0.222153 0.836471 0.464212 0.274 Uiso 0.0844 1 calc GR . P A 2
S4A S 0.2251(4) 0.7983(8) 0.7601(4) 0.148(3) Uani 0.4006 1 d . . P B 2
S2A S 0.3290(18) 0.798(3) 0.4633(12) 0.128(6) Uani 0.0844 1 d . U P A 2
O2 O 0.2985(3) 0.5324(8) 0.5836(3) 0.165(3) Uani 1 1 d D U . . .
S3 S 0.2503(3) 0.4289(7) 0.5962(2) 0.145(2) Uani 0.5365 1 d D U P C 1
S3A S 0.2577(4) 0.5139(9) 0.6250(3) 0.146(2) Uani 0.4635 1 d D U P C 2
C16 C 0.1695(5) 0.5113(15) 0.6101(4) 0.206(5) Uani 1 1 d . U . . .
H16A H 0.176539 0.608596 0.609255 0.309 Uiso 0.5365 1 calc GR . P C 1
H16B H 0.154139 0.484407 0.641317 0.309 Uiso 0.5365 1 calc GR . P C 1
H16C H 0.133456 0.486125 0.587221 0.309 Uiso 0.5365 1 calc GR . P C 1
H16D H 0.162157 0.565148 0.581894 0.309 Uiso 0.4635 1 calc GR . P C 2
H16E H 0.141564 0.548606 0.635702 0.309 Uiso 0.4635 1 calc GR . P C 2
H16F H 0.154763 0.418704 0.604144 0.309 Uiso 0.4635 1 calc GR . P C 2
C17 C 0.2620(9) 0.3758(19) 0.6537(6) 0.264(7) Uani 1 1 d . U . . .
H17A H 0.306261 0.325874 0.656219 0.396 Uiso 0.5365 1 calc GR . P C 1
H17B H 0.222664 0.317620 0.662735 0.396 Uiso 0.5365 1 calc GR . P C 1
H17C H 0.263507 0.453909 0.674363 0.396 Uiso 0.5365 1 calc GR . P C 1
H17D H 0.282623 0.305903 0.633929 0.396 Uiso 0.4635 1 calc GR . P C 2
H17E H 0.214484 0.348656 0.663216 0.396 Uiso 0.4635 1 calc GR . P C 2
H17F H 0.291360 0.388493 0.681420 0.396 Uiso 0.4635 1 calc GR . 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 C2 1.752(6) . ?
S1 C7 1.773(6) 5_666 ?
S5 C4 1.819(6) . ?
S5 C6 1.768(6) . ?
S2 O1 1.473(5) . ?
S2 C14 1.709(10) . ?
S2 C15 1.688(9) . ?
Cl1 C11 1.749(6) . ?
S4 O3 1.392(12) . ?
S4 C19 1.697(12) . ?
S4 C18 1.781(11) . ?
O1 S2A 1.64(3) . ?
N1 C2 1.326(7) . ?
C3 C4 1.499(7) . ?
C3 C2 1.361(7) . ?
C3 C3' 1.419(9) . ?
C8 C4 1.504(8) . ?
C8 C9 1.368(8) . ?
C8 C13 1.397(8) . ?
C7 C6 1.466(7) . ?
C11 C12 1.330(8) . ?
C11 C10 1.353(9) . ?
C12 C13 1.386(8) . ?
C9 C10 1.364(9) . ?
C3' N2 1.118(7) . ?
O3 S4A 1.365(10) . ?
C19 S4A 1.694(14) . ?
C14 S2A 1.69(3) . ?
C18 S4A 1.711(11) . ?
C15 S2A 1.49(3) . ?
O2 S3 1.397(8) . ?
O2 S3A 1.400(9) . ?
S3 C16 1.749(12) . ?
S3 C17 1.710(15) . ?
S3A C16 1.694(12) . ?
S3A C17 1.575(16) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 S1 C7 102.6(3) . 5_666 ?
C6 S5 C4 102.3(3) . . ?
O1 S2 C14 109.4(4) . . ?
O1 S2 C15 106.3(5) . . ?
C15 S2 C14 101.3(6) . . ?
O3 S4 C19 112.7(7) . . ?
O3 S4 C18 106.3(6) . . ?
C19 S4 C18 95.3(6) . . ?
C2 C3 C4 123.6(5) . . ?
C2 C3 C3' 119.7(5) . . ?
C3'K C3 C4 116.7(5) . . ?
C9 C8 C4 119.4(6) . . ?
C9 C8 C13 118.6(6) . . ?
C13 C8 C4 122.0(6) . . ?
C3 C4 S5 113.6(4) . . ?
C3 C4 C8 114.0(5) . . ?
C8 C4 S5 108.1(4) . . ?
N1 C2 S1 117.5(4) . . ?
N1 C2 C3 124.0(5) . . ?
C3 C2 S1 118.4(5) . . ?
C6 C7 S1 115.7(4) . 5_666 ?
C12 C11 Cl1 118.2(5) . . ?
C12 C11 C10 122.5(6) . . ?
C10 C11 Cl1 119.2(5) . . ?
C7 C6 S5 111.7(4) . . ?
C11 C12 C13 119.5(6) . . ?
C10 C9 C8 121.1(6) . . ?
C12 C13 C8 119.3(6) . . ?
N2 C3' C3 176.4(8) . . ?
C11 C10 C9 118.9(6) . . ?
O3 S4A C19 114.4(9) . . ?
O3 S4A C18 111.5(8) . . ?
C19 S4A C18 98.0(7) . . ?
O1 S2A C14 102.7(17) . . ?
C15 S2A O1 108(2) . . ?
C15 S2A C14 111(2) . . ?
O2 S3 C16 106.0(7) . . ?
O2 S3 C17 112.2(8) . . ?
C17 S3 C16 92.2(8) . . ?
O2 S3A C16 108.8(7) . . ?
O2 S3A C17 120.6(9) . . ?
C17 S3A C16 99.4(9) . . ?


