# Electronic Supplementary Material (ESI) for Inorganic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_17
_database_code_depnum_ccdc_archive 'CCDC 2051041'
loop_
_audit_author_name
_audit_author_address
'Felix Hennersdorf'
;TU Dresden
Germany
;
_audit_update_record             
;
2020-12-17 deposited with the CCDC.	2021-04-01 downloaded from the CCDC.
;
_audit_creation_date             2019-07-19
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H16 N2 O2 S'
_chemical_formula_sum            'C19 H16 N2 O2 S'
_chemical_formula_weight         336.40
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C80 H68 N4 O8 S4 '
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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                   16.5728(2)
_cell_length_b                   5.43550(10)
_cell_length_c                   18.1303(2)
_cell_angle_alpha                90
_cell_angle_beta                 101.7630(10)
_cell_angle_gamma                90
_cell_volume                     1598.91(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7734
_cell_measurement_temperature    100.00(11)
_cell_measurement_theta_max      76.2580
_cell_measurement_theta_min      2.7150
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.912
_exptl_absorpt_correction_T_max  0.893
_exptl_absorpt_correction_T_min  0.676
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.397
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             704
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
2 -3 0 0.2034
-4 0 -5 0.0922
4 0 5 0.1045
-3 -1 -5 0.1143
-5 0 2 0.0616
-5 -1 2 0.0976
-2 0 5 0.0684
2 1 5 0.1241
-3 0 -5 0.0895
5 1 1 0.0917
5 0 1 0.0826
5 0 -2 0.0450
-5 0 4 0.0540
5 0 -4 0.0342
3 0 -5 0.0242
-5 -2 -2 0.1364
5 1 -4 0.0400

_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.196
_exptl_crystal_size_min          0.088
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
1.9928 -2.9998 -0.0005 -0.0262 -0.0036 -0.8706
-4.0012 -0.0005 -4.9976 0.5823 0.2316 0.0830
4.0012 0.0005 4.9976 -0.5823 -0.2316 -0.0830
-3.0036 -1.0005 -4.9981 0.5602 0.2025 -0.2136
-4.9988 0.0004 2.0049 0.0325 0.4607 0.0925
-5.0011 -0.9995 2.0054 0.0505 0.5154 -0.1850
-1.9981 0.0007 5.0030 -0.3411 0.2714 0.0313
2.0037 1.0005 4.9990 -0.5200 -0.1187 0.2326
-3.0013 -0.0006 -4.9985 0.5421 0.1478 0.0640
5.0021 0.9999 0.9954 -0.3034 -0.4532 0.1809
4.9998 -0.0000 0.9958 -0.2854 -0.3984 -0.0966
4.9988 -0.0004 -2.0049 -0.0325 -0.4607 -0.0925
-4.9981 0.0007 4.0054 -0.1361 0.5022 0.0898
4.9981 -0.0007 -4.0054 0.1361 -0.5022 -0.0898
2.9980 -0.0008 -5.0039 0.3009 -0.3552 -0.0504
-5.0047 -1.9999 -1.9952 0.4058 0.4871 -0.4570
5.0004 0.9992 -4.0059 0.1181 -0.5569 0.1877

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0237
_diffrn_reflns_av_unetI/netI     0.0185
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            13858
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.657
_diffrn_reflns_theta_min         2.723
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(11)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.5700
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -28.00  65.00   0.50    1.00    --   42.75 -38.00 -30.00  186
  2  ω     40.00  82.00   0.50    1.00    --   42.75 -99.00  30.00   84
  3  ω     48.00  94.00   0.50    4.00    --  111.00-125.00  60.00   92
  4  ω     77.00 115.00   0.50    4.00    --  111.00-125.00  90.00   76
  5  ω     88.00 139.00   0.50    4.00    --  111.00 -77.00  90.00  102
  6  ω    110.00 135.00   0.50    4.00    --  111.00 -45.00  90.00   50
  7  ω    119.00 155.00   0.50    4.00    --  111.00  15.00 150.00   72
  8  ω     78.00 109.00   0.50    4.00    --  111.00 -94.00  90.00   62
  9  ω     50.00  87.00   0.50    4.00    --  111.00 -45.00  90.00   74
 10  ω     41.00 148.00   0.50    4.00    --  111.00 -15.00 150.00  214
 11  ω     68.00 106.00   0.50    4.00    --  111.00  15.00 150.00   76
 12  ω     45.00  70.00   0.50    4.00    --  111.00 -77.00  90.00   50
 13  ω     41.00  68.00   0.50    4.00    --  111.00 -94.00  90.00   54
 14  ω     34.00 107.00   0.50    4.00    --  111.00 -94.00 -30.00  146
 15  ω     71.00 102.00   0.50    4.00    --  111.00 -94.00 -90.00   62
 16  ω     45.00 131.00   0.50    4.00    --  111.00 -45.00 -60.00  172
 17  ω    111.00 152.00   0.50    4.00    --  111.00 -15.00 -90.00   82
 18  ω     95.00 170.00   0.50    4.00    --  111.00  45.00-180.00  150
 19  ω     95.00 163.00   0.50    4.00    --  111.00 125.00-120.00  136
 20  ω     81.00 111.00   0.50    4.00    --  111.00  77.00-180.00   60
 21  ω     41.00  91.00   0.50    4.00    --  111.00 -15.00 -90.00  100
 22  ω     40.00 128.00   0.50    4.00    --  111.00 -45.00-150.00  176
 23  ω     46.00  91.00   0.50    4.00    --  111.00 -94.00-120.00   90
 24  ω     33.00  61.00   0.50    1.00    --   42.75 -38.00-120.00   56
 25  ω    -30.00  -3.00   0.50    1.00    --   42.75 -38.00-120.00   54
 26  ω    -65.00  28.00   0.50    1.00    --  -38.50  57.00 -90.00  186
 27  ω   -109.00 -17.00   0.50    1.00    --  -38.50 -57.00 120.00  184
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0402939000
_diffrn_orient_matrix_UB_12      -0.0180176000
_diffrn_orient_matrix_UB_13      -0.0842623000
_diffrn_orient_matrix_UB_21      -0.0838310000
_diffrn_orient_matrix_UB_22      -0.0545062000
_diffrn_orient_matrix_UB_23      0.0207711000
_diffrn_orient_matrix_UB_31      -0.0190465000
_diffrn_orient_matrix_UB_32      0.2775758000
_diffrn_orient_matrix_UB_33      -0.0013911000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3156
_reflns_number_total             3338
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_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         0.320
_refine_diff_density_min         -0.493
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         3338
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0338
_refine_ls_R_factor_gt           0.0322
_refine_ls_restrained_S_all      1.040
_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)+(0.0529P)²+0.6166P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0872
_refine_ls_wR_factor_ref         0.0887
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C7(H7), C9(H9), C10(H10), C11(H11),
 C12(H12), C13(H13), C15(H15), C16(H16), C17(H17), C18(H18), C19(H19)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.42061(7) 0.3752(2) 0.37073(7) 0.0185(2) Uani 1 1 d . . . . .
C2 C 0.47755(9) 0.2537(3) 0.42552(8) 0.0261(3) Uani 1 1 d . . . . .
H2 H 0.4618 0.1168 0.4499 0.031 Uiso 1 1 calc R . . . .
C3 C 0.55800(9) 0.3385(3) 0.44337(9) 0.0317(3) Uani 1 1 d . . . . .
H3 H 0.5964 0.2598 0.4804 0.038 Uiso 1 1 calc R . . . .
C4 C 0.58118(9) 0.5402(3) 0.40608(9) 0.0307(3) Uani 1 1 d . . . . .
H4 H 0.6352 0.5966 0.4181 0.037 Uiso 1 1 calc R . . . .
C5 C 0.52417(9) 0.6591(3) 0.35071(10) 0.0319(3) Uani 1 1 d . . . . .
H5 H 0.5404 0.7935 0.3255 0.038 Uiso 1 1 calc R . . . .
C6 C 0.44287(9) 0.5776(3) 0.33279(8) 0.0254(3) Uani 1 1 d . . . . .
H6 H 0.4043 0.6573 0.2961 0.030 Uiso 1 1 calc R . . . .
C7 C 0.21327(7) 0.5590(2) 0.38071(6) 0.0158(2) Uani 1 1 d . . . . .
H7 H 0.1995 0.5745 0.3286 0.019 Uiso 1 1 calc R . . . .
C8 C 0.19258(7) 0.6736(2) 0.50428(6) 0.0159(2) Uani 1 1 d . . . . .
C9 C 0.23821(7) 0.8676(2) 0.54100(7) 0.0179(2) Uani 1 1 d . . . . .
H9 H 0.2536 0.9981 0.5137 0.021 Uiso 1 1 calc R . . . .
C10 C 0.26071(8) 0.8645(2) 0.61940(7) 0.0200(3) Uani 1 1 d . . . . .
H10 H 0.2910 0.9940 0.6448 0.024 Uiso 1 1 calc R . . . .
C11 C 0.23790(8) 0.6676(2) 0.65955(7) 0.0203(3) Uani 1 1 d . . . . .
H11 H 0.2534 0.6651 0.7118 0.024 Uiso 1 1 calc R . . . .
C12 C 0.19206(8) 0.4744(2) 0.62207(7) 0.0205(3) Uani 1 1 d . . . . .
H12 H 0.1770 0.3432 0.6493 0.025 Uiso 1 1 calc R . . . .
C13 C 0.16863(7) 0.4769(2) 0.54370(7) 0.0185(2) Uani 1 1 d . . . . .
H13 H 0.1375 0.3490 0.5183 0.022 Uiso 1 1 calc R . . . .
C14 C 0.10520(7) 0.8494(2) 0.39022(6) 0.0159(2) Uani 1 1 d . . . . .
C15 C 0.03338(8) 0.8588(2) 0.41951(7) 0.0194(2) Uani 1 1 d . . . . .
H15 H 0.0264 0.7512 0.4576 0.023 Uiso 1 1 calc R . . . .
C16 C -0.02736(8) 1.0296(2) 0.39136(7) 0.0210(3) Uani 1 1 d . . . . .
H16 H -0.0748 1.0378 0.4112 0.025 Uiso 1 1 calc R . . . .
C17 C -0.01770(8) 1.1888(2) 0.33366(7) 0.0205(3) Uani 1 1 d . . . . .
H17 H -0.0582 1.3045 0.3154 0.025 Uiso 1 1 calc R . . . .
C18 C 0.05280(8) 1.1739(2) 0.30351(7) 0.0197(2) Uani 1 1 d . . . . .
H18 H 0.0587 1.2772 0.2641 0.024 Uiso 1 1 calc R . . . .
C19 C 0.11458(7) 1.0053(2) 0.33194(7) 0.0175(2) Uani 1 1 d . . . . .
H19 H 0.1619 0.9972 0.3120 0.021 Uiso 1 1 calc R . . . .
N1 N 0.27476(6) 0.41903(19) 0.41052(5) 0.0165(2) Uani 1 1 d . . . . .
N2 N 0.16907(6) 0.68176(19) 0.42298(6) 0.0161(2) Uani 1 1 d . . . . .
O1 O 0.31906(6) 0.01245(16) 0.37144(5) 0.0220(2) Uani 1 1 d . . . . .
O2 O 0.28147(6) 0.32985(18) 0.27347(5) 0.0218(2) Uani 1 1 d . . . . .
S1 S 0.31818(2) 0.26807(5) 0.35057(2) 0.01582(10) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.3897(19) . ?
C1 C6 1.3867(19) . ?
C1 S1 1.7610(12) . ?
C2 H2 0.9300 . ?
C2 C3 1.385(2) . ?
C3 H3 0.9300 . ?
C3 C4 1.383(2) . ?
C4 H4 0.9300 . ?
C4 C5 1.390(2) . ?
C5 H5 0.9300 . ?
C5 C6 1.392(2) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C7 N1 1.2979(16) . ?
C7 N2 1.3410(16) . ?
C8 C9 1.3863(17) . ?
C8 C13 1.3883(17) . ?
C8 N2 1.4465(14) . ?
C9 H9 0.9300 . ?
C9 C10 1.3941(17) . ?
C10 H10 0.9300 . ?
C10 C11 1.3892(19) . ?
C11 H11 0.9300 . ?
C11 C12 1.3898(19) . ?
C12 H12 0.9300 . ?
C12 C13 1.3946(17) . ?
C13 H13 0.9300 . ?
C14 C15 1.3997(17) . ?
C14 C19 1.3876(17) . ?
C14 N2 1.4309(15) . ?
C15 H15 0.9300 . ?
C15 C16 1.3881(18) . ?
C16 H16 0.9300 . ?
C16 C17 1.3915(18) . ?
C17 H17 0.9300 . ?
C17 C18 1.3895(18) . ?
C18 H18 0.9300 . ?
C18 C19 1.3923(17) . ?
C19 H19 0.9300 . ?
N1 S1 1.6404(10) . ?
O1 S1 1.4393(9) . ?
O2 S1 1.4457(9) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 S1 118.46(10) . . ?
C6 C1 C2 121.40(12) . . ?
C6 C1 S1 120.14(10) . . ?
C1 C2 H2 120.3 . . ?
C3 C2 C1 119.33(14) . . ?
C3 C2 H2 120.3 . . ?
C2 C3 H3 120.0 . . ?
C4 C3 C2 119.98(14) . . ?
C4 C3 H3 120.0 . . ?
C3 C4 H4 119.8 . . ?
C3 C4 C5 120.39(13) . . ?
C5 C4 H4 119.8 . . ?
C4 C5 H5 119.9 . . ?
C4 C5 C6 120.25(14) . . ?
C6 C5 H5 119.9 . . ?
C1 C6 C5 118.64(13) . . ?
C1 C6 H6 120.7 . . ?
C5 C6 H6 120.7 . . ?
N1 C7 H7 119.1 . . ?
N1 C7 N2 121.85(11) . . ?
N2 C7 H7 119.1 . . ?
C9 C8 C13 121.59(11) . . ?
C9 C8 N2 118.25(11) . . ?
C13 C8 N2 120.15(11) . . ?
C8 C9 H9 120.4 . . ?
C8 C9 C10 119.12(11) . . ?
C10 C9 H9 120.4 . . ?
C9 C10 H10 120.0 . . ?
C11 C10 C9 119.93(12) . . ?
C11 C10 H10 120.0 . . ?
C10 C11 H11 119.8 . . ?
C10 C11 C12 120.40(11) . . ?
C12 C11 H11 119.8 . . ?
C11 C12 H12 119.9 . . ?
C11 C12 C13 120.11(12) . . ?
C13 C12 H12 119.9 . . ?
C8 C13 C12 118.86(12) . . ?
C8 C13 H13 120.6 . . ?
C12 C13 H13 120.6 . . ?
C15 C14 N2 118.68(11) . . ?
C19 C14 C15 120.18(11) . . ?
C19 C14 N2 121.11(11) . . ?
C14 C15 H15 120.2 . . ?
C16 C15 C14 119.59(11) . . ?
C16 C15 H15 120.2 . . ?
C15 C16 H16 119.8 . . ?
C15 C16 C17 120.43(12) . . ?
C17 C16 H16 119.8 . . ?
C16 C17 H17 120.2 . . ?
C18 C17 C16 119.62(12) . . ?
C18 C17 H17 120.2 . . ?
C17 C18 H18 119.8 . . ?
C17 C18 C19 120.44(12) . . ?
C19 C18 H18 119.8 . . ?
C14 C19 C18 119.71(11) . . ?
C14 C19 H19 120.1 . . ?
C18 C19 H19 120.1 . . ?
C7 N1 S1 115.50(8) . . ?
C7 N2 C8 120.14(10) . . ?
C7 N2 C14 121.60(10) . . ?
C14 N2 C8 117.72(9) . . ?
N1 S1 C1 103.39(5) . . ?
O1 S1 C1 107.88(6) . . ?
O1 S1 N1 106.92(5) . . ?
O1 S1 O2 117.27(6) . . ?
O2 S1 C1 108.77(6) . . ?
O2 S1 N1 111.68(5) . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.480
_oxdiff_exptl_absorpt_empirical_full_min 0.643
####################################################################### 
# 
# 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_23b
_database_code_depnum_ccdc_archive 'CCDC 2051044'
loop_
_audit_author_name
_audit_author_address
'Felix Hennersdorf'
;TU Dresden
Germany
;
_audit_update_record             
;
2020-12-17 deposited with the CCDC.	2021-04-01 downloaded from the CCDC.
;
_audit_creation_date             2018-02-13
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C10 H14 N2 O2 S'
_chemical_formula_sum            'C10 H14 N2 O2 S'
_chemical_formula_weight         226.29
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C136 H180 N8 O24 S12 '
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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                   7.49968(10)
_cell_length_b                   25.7462(3)
_cell_length_c                   17.1284(3)
_cell_angle_alpha                90
_cell_angle_beta                 94.8660(13)
_cell_angle_gamma                90
_cell_volume                     3295.39(8)
_cell_formula_units_Z            12
_cell_measurement_reflns_used    11368
_cell_measurement_temperature    100.0(2)
_cell_measurement_theta_max      76.3110
_cell_measurement_theta_min      3.0940
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.488
_exptl_absorpt_correction_T_max  0.620
_exptl_absorpt_correction_T_min  0.394
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.368
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1440
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 16 -3 0.0380
0 -16 3 0.0275
5 1 3 0.0509
-4 5 -4 0.0630
0 3 11 0.0324
0 -3 -11 0.0324
2 -15 -3 0.0526
-2 15 3 0.0475
-1 -6 10 0.0295
-3 12 2 0.0540
-5 2 3 0.0572
5 -3 -2 0.0559
0 16 4 0.0310
3 -1 9 0.0395

_exptl_crystal_size_max          0.128
_exptl_crystal_size_mid          0.065
_exptl_crystal_size_min          0.065
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-0.0003 16.0028 -2.9976 0.0226 -0.5122 -0.8522
0.0003 -16.0028 2.9976 -0.0226 0.5122 0.8522
4.9955 1.0016 3.0043 -0.0525 -0.9123 0.5917
-3.9964 5.0000 -4.0022 0.0093 0.5515 -0.8025
-0.0027 2.9937 10.9920 0.9279 -0.2626 0.2956
0.0027 -2.9937 -10.9920 -0.9279 0.2626 -0.2956
2.0001 -14.9978 -2.9954 -0.6089 0.2302 0.7778
-2.0001 14.9978 2.9954 0.6089 -0.2302 -0.7778
-1.0012 -6.0070 9.9913 0.7622 0.2311 0.5653
-2.9989 11.9976 1.9948 0.5416 0.0552 -0.7834
-4.9970 1.9950 2.9914 0.5810 0.7217 -0.4930
4.9969 -2.9957 -1.9921 -0.5175 -0.7014 0.5783
-0.0019 15.9986 3.9973 0.5817 -0.6130 -0.5765
2.9958 -1.0034 8.9973 0.5174 -0.5955 0.7120

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0195
_diffrn_reflns_av_unetI/netI     0.0213
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            18870
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.587
_diffrn_reflns_theta_min         3.107
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.0(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2850
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -68.00  30.00   0.50    2.00    --  -38.50  77.00  30.00  196
  2  ω    -49.00  32.00   0.50    2.00    --  -38.50  38.00 -60.00  162
  3  ω     32.00  79.00   0.50    2.00    --   42.50-125.00-180.00   94
  4  ω     39.00  66.00   0.50    2.00    --   42.50-125.00-120.00   54
  5  ω     32.00 108.00   0.50    8.00    --  111.00 -94.00 150.00  152
  6  ω     89.00 175.00   0.50    8.00    --  111.00  45.00   0.00  172
  7  ω    102.00 168.00   0.50    8.00    --  111.00  45.00 -30.00  132
  8  ω     38.00  84.00   0.50    8.00    --  111.00 -94.00-180.00   92
  9  ω    115.00 165.00   0.50    8.00    --  111.00 125.00-120.00  100
 10  ω     39.00  64.00   0.50    8.00    --  111.00 -94.00 -30.00   50
 11  ω     44.00 135.00   0.50    8.00    --  111.00 -45.00-180.00  182
 12  ω     95.00 178.00   0.50    8.00    --  111.00  30.00 -60.00  166
 13  ω     39.00 105.00   0.50    8.00    --  111.00-125.00  90.00  132
 14  ω     36.00 102.00   0.50    8.00    --  111.00 -94.00-150.00  132
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0618744000
_diffrn_orient_matrix_UB_12      0.0163824000
_diffrn_orient_matrix_UB_13      0.0799344000
_diffrn_orient_matrix_UB_21      -0.1669513000
_diffrn_orient_matrix_UB_22      -0.0347208000
_diffrn_orient_matrix_UB_23      -0.0144715000
_diffrn_orient_matrix_UB_31      0.1039477000
_diffrn_orient_matrix_UB_32      -0.0458682000
_diffrn_orient_matrix_UB_33      0.0394132000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                6491
_reflns_number_total             6884
_reflns_odcompleteness_completeness 99.99
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_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 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_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         0.712
_refine_diff_density_min         -0.452
_refine_diff_density_rms         0.074
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.148
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     415
_refine_ls_number_reflns         6884
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0516
_refine_ls_R_factor_gt           0.0495
_refine_ls_restrained_S_all      1.148
_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)+(0.0386P)²+7.0425P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1341
_refine_ls_wR_factor_ref         0.1353
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1A(H1A), C5A(H5A), C6A(H6A), C8A(H8A), C9A(H9A), C1B(H1B), C5B(H5B),
 C6B(H6B), C8B(H8B), C9B(H9B), C1C(H1C), C5C(H5C), C6C(H6C), C8C(H8C), C9C(H9C)
2.b Idealised Me refined as rotating group:
 C2A(H2AA,H2AB,H2AC), C3A(H3AA,H3AB,H3AC), C10A(H10A,H10B,H10C), C2B(H2BA,H2BB,
 H2BC), C3B(H3BA,H3BB,H3BC), C10B(H10D,H10E,H10F), C2C(H2CA,H2CB,H2CC),
 C3C(H3CA,H3CB,H3CC), C10C(H10G,H10H,H10I)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1A S 0.32919(8) 0.39825(2) 0.55221(3) 0.01646(14) Uani 1 1 d . . . . .
O1A O 0.3652(3) 0.40120(7) 0.63633(10) 0.0236(4) Uani 1 1 d . . . . .
O2A O 0.1799(2) 0.42780(7) 0.51708(11) 0.0209(4) Uani 1 1 d . . . . .
N1A N 0.5140(3) 0.41230(8) 0.51471(12) 0.0181(4) Uani 1 1 d . . . . .
N2A N 0.6350(3) 0.44292(8) 0.40427(12) 0.0170(4) Uani 1 1 d . . . . .
C1A C 0.4969(3) 0.43051(9) 0.44217(14) 0.0162(5) Uani 1 1 d . . . . .
H1A H 0.3826 0.4346 0.4173 0.019 Uiso 1 1 calc R . . . .
C2A C 0.6142(4) 0.46522(10) 0.32561(15) 0.0212(5) Uani 1 1 d . . . . .
H2AA H 0.4930 0.4606 0.3038 0.032 Uiso 1 1 calc GR . . . .
H2AB H 0.6940 0.4481 0.2930 0.032 Uiso 1 1 calc GR . . . .
H2AC H 0.6420 0.5016 0.3283 0.032 Uiso 1 1 calc GR . . . .
C3A C 0.8180(3) 0.43826(10) 0.44099(15) 0.0199(5) Uani 1 1 d . . . . .
H3AA H 0.8528 0.4704 0.4664 0.030 Uiso 1 1 calc GR . . . .
H3AB H 0.8979 0.4306 0.4016 0.030 Uiso 1 1 calc GR . . . .
H3AC H 0.8231 0.4108 0.4790 0.030 Uiso 1 1 calc GR . . . .
C4A C 0.2876(3) 0.33215(9) 0.52898(14) 0.0163(5) Uani 1 1 d . . . . .
C5A C 0.1667(3) 0.31894(10) 0.46613(14) 0.0187(5) Uani 1 1 d . . . . .
H5A H 0.1073 0.3447 0.4359 0.022 Uiso 1 1 calc R . . . .
C6A C 0.1358(3) 0.26674(10) 0.44901(14) 0.0193(5) Uani 1 1 d . . . . .
H6A H 0.0536 0.2577 0.4075 0.023 Uiso 1 1 calc R . . . .
C7A C 0.2254(3) 0.22779(10) 0.49281(15) 0.0193(5) Uani 1 1 d . . . . .
C8A C 0.3458(3) 0.24189(10) 0.55595(15) 0.0210(5) Uani 1 1 d . . . . .
H8A H 0.4054 0.2162 0.5861 0.025 Uiso 1 1 calc R . . . .
C9A C 0.3774(3) 0.29375(10) 0.57430(14) 0.0193(5) Uani 1 1 d . . . . .
H9A H 0.4578 0.3028 0.6164 0.023 Uiso 1 1 calc R . . . .
C10A C 0.1928(4) 0.17165(10) 0.47280(18) 0.0283(6) Uani 1 1 d . . . . .
H10A H 0.1266 0.1558 0.5121 0.042 Uiso 1 1 calc GR . . . .
H10B H 0.3053 0.1542 0.4708 0.042 Uiso 1 1 calc GR . . . .
H10C H 0.1255 0.1691 0.4227 0.042 Uiso 1 1 calc GR . . . .
S1B S 0.23309(8) 0.39810(2) 0.88688(3) 0.01643(14) Uani 1 1 d . . . . .
O1B O 0.2303(2) 0.40331(7) 0.97080(10) 0.0216(4) Uani 1 1 d . . . . .
O2B O 0.3834(2) 0.42041(7) 0.85124(11) 0.0213(4) Uani 1 1 d . . . . .
N1B N 0.0422(3) 0.41906(8) 0.84845(12) 0.0171(4) Uani 1 1 d . . . . .
N2B N -0.1171(3) 0.44322(8) 0.73395(12) 0.0162(4) Uani 1 1 d . . . . .
C1B C 0.0367(3) 0.43333(9) 0.77422(14) 0.0165(5) Uani 1 1 d . . . . .
H1B H 0.1427 0.4364 0.7501 0.020 Uiso 1 1 calc R . . . .
C2B C -0.1232(4) 0.46213(10) 0.65346(14) 0.0208(5) Uani 1 1 d . . . . .
H2BA H -0.1520 0.4985 0.6523 0.031 Uiso 1 1 calc GR . . . .
H2BB H -0.2130 0.4434 0.6216 0.031 Uiso 1 1 calc GR . . . .
H2BC H -0.0087 0.4570 0.6335 0.031 Uiso 1 1 calc GR . . . .
C3B C -0.2865(3) 0.43691(10) 0.76929(15) 0.0188(5) Uani 1 1 d . . . . .
H3BA H -0.2762 0.4089 0.8063 0.028 Uiso 1 1 calc GR . . . .
H3BB H -0.3800 0.4293 0.7291 0.028 Uiso 1 1 calc GR . . . .
H3BC H -0.3145 0.4684 0.7956 0.028 Uiso 1 1 calc GR . . . .
C4B C 0.2259(3) 0.33107(10) 0.86429(14) 0.0168(5) Uani 1 1 d . . . . .
C5B C 0.2804(3) 0.31439(10) 0.79281(15) 0.0207(5) Uani 1 1 d . . . . .
H5B H 0.3296 0.3377 0.7591 0.025 Uiso 1 1 calc R . . . .
C6B C 0.2600(3) 0.26238(10) 0.77267(15) 0.0212(5) Uani 1 1 d . . . . .
H6B H 0.2962 0.2510 0.7250 0.025 Uiso 1 1 calc R . . . .
C7B C 0.1866(3) 0.22680(10) 0.82231(15) 0.0197(5) Uani 1 1 d . . . . .
C8B C 0.1349(3) 0.24439(10) 0.89394(15) 0.0219(5) Uani 1 1 d . . . . .
H8B H 0.0871 0.2211 0.9281 0.026 Uiso 1 1 calc R . . . .
C9B C 0.1542(3) 0.29633(10) 0.91478(15) 0.0206(5) Uani 1 1 d . . . . .
H9B H 0.1189 0.3078 0.9626 0.025 Uiso 1 1 calc R . . . .
C10B C 0.1655(4) 0.17094(10) 0.79857(18) 0.0278(6) Uani 1 1 d . . . . .
H10D H 0.1293 0.1689 0.7435 0.042 Uiso 1 1 calc GR . . . .
H10E H 0.0761 0.1550 0.8276 0.042 Uiso 1 1 calc GR . . . .
H10F H 0.2774 0.1532 0.8094 0.042 Uiso 1 1 calc GR . . . .
S1C S 0.14233(8) 0.40363(2) 0.21773(3) 0.01569(14) Uani 1 1 d . . . . .
O1C O 0.1324(2) 0.40634(7) 0.30145(10) 0.0223(4) Uani 1 1 d . . . . .
O2C O 0.2714(2) 0.43645(7) 0.18395(11) 0.0204(4) Uani 1 1 d . . . . .
N1C N -0.0579(3) 0.41349(8) 0.17812(12) 0.0174(4) Uani 1 1 d . . . . .
N2C N -0.2227(3) 0.44430(8) 0.06796(12) 0.0160(4) Uani 1 1 d . . . . .
C1C C -0.0687(3) 0.43160(9) 0.10530(14) 0.0155(5) Uani 1 1 d . . . . .
H1C H 0.0356 0.4354 0.0801 0.019 Uiso 1 1 calc R . . . .
C2C C -0.2329(3) 0.46471(10) -0.01187(14) 0.0197(5) Uani 1 1 d . . . . .
H2CA H -0.2598 0.5012 -0.0111 0.030 Uiso 1 1 calc GR . . . .
H2CB H -0.3253 0.4468 -0.0435 0.030 Uiso 1 1 calc GR . . . .
H2CC H -0.1202 0.4596 -0.0335 0.030 Uiso 1 1 calc GR . . . .
C3C C -0.3901(3) 0.44217(10) 0.10578(15) 0.0205(5) Uani 1 1 d . . . . .
H3CA H -0.3799 0.4168 0.1469 0.031 Uiso 1 1 calc GR . . . .
H3CB H -0.4862 0.4328 0.0678 0.031 Uiso 1 1 calc GR . . . .
H3CC H -0.4140 0.4756 0.1274 0.031 Uiso 1 1 calc GR . . . .
C4C C 0.2008(3) 0.33893(9) 0.19610(14) 0.0159(5) Uani 1 1 d . . . . .
C5C C 0.2825(3) 0.32803(10) 0.12799(14) 0.0190(5) Uani 1 1 d . . . . .
H5C H 0.3019 0.3543 0.0925 0.023 Uiso 1 1 calc R . . . .
C6C C 0.3347(3) 0.27752(10) 0.11370(15) 0.0215(5) Uani 1 1 d . . . . .
H6C H 0.3877 0.2701 0.0678 0.026 Uiso 1 1 calc R . . . .
C7C C 0.3097(3) 0.23744(10) 0.16659(16) 0.0202(5) Uani 1 1 d . . . . .
C8C C 0.2280(4) 0.24935(10) 0.23411(16) 0.0240(5) Uani 1 1 d . . . . .
H8C H 0.2096 0.2231 0.2699 0.029 Uiso 1 1 calc R . . . .
C9C C 0.1732(4) 0.29952(10) 0.24928(15) 0.0212(5) Uani 1 1 d . . . . .
H9C H 0.1184 0.3068 0.2947 0.025 Uiso 1 1 calc R . . . .
C10C C 0.3674(4) 0.18282(11) 0.14977(19) 0.0292(6) Uani 1 1 d . . . . .
H10G H 0.2800 0.1668 0.1132 0.044 Uiso 1 1 calc GR . . . .
H10H H 0.3780 0.1632 0.1976 0.044 Uiso 1 1 calc GR . . . .
H10I H 0.4810 0.1836 0.1278 0.044 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1A O1A 1.4452(18) . ?
S1A O2A 1.4424(18) . ?
S1A N1A 1.617(2) . ?
S1A C4A 1.769(2) . ?
N1A C1A 1.324(3) . ?
N2A C1A 1.308(3) . ?
N2A C2A 1.461(3) . ?
N2A C3A 1.465(3) . ?
C1A H1A 0.9300 . ?
C2A H2AA 0.9600 . ?
C2A H2AB 0.9600 . ?
C2A H2AC 0.9600 . ?
C3A H3AA 0.9600 . ?
C3A H3AB 0.9600 . ?
C3A H3AC 0.9600 . ?
C4A C5A 1.390(3) . ?
C4A C9A 1.394(3) . ?
C5A H5A 0.9300 . ?
C5A C6A 1.391(4) . ?
C6A H6A 0.9300 . ?
C6A C7A 1.391(4) . ?
C7A C8A 1.397(4) . ?
C7A C10A 1.501(4) . ?
C8A H8A 0.9300 . ?
C8A C9A 1.388(4) . ?
C9A H9A 0.9300 . ?
C10A H10A 0.9600 . ?
C10A H10B 0.9600 . ?
C10A H10C 0.9600 . ?
S1B O1B 1.4456(18) . ?
S1B O2B 1.4460(18) . ?
S1B N1B 1.617(2) . ?
S1B C4B 1.768(3) . ?
N1B C1B 1.321(3) . ?
N2B C1B 1.318(3) . ?
N2B C2B 1.459(3) . ?
N2B C3B 1.462(3) . ?
C1B H1B 0.9300 . ?
C2B H2BA 0.9600 . ?
C2B H2BB 0.9600 . ?
C2B H2BC 0.9600 . ?
C3B H3BA 0.9600 . ?
C3B H3BB 0.9600 . ?
C3B H3BC 0.9600 . ?
C4B C5B 1.391(3) . ?
C4B C9B 1.384(3) . ?
C5B H5B 0.9300 . ?
C5B C6B 1.388(4) . ?
C6B H6B 0.9300 . ?
C6B C7B 1.394(4) . ?
C7B C8B 1.393(4) . ?
C7B C10B 1.499(4) . ?
C8B H8B 0.9300 . ?
C8B C9B 1.388(4) . ?
C9B H9B 0.9300 . ?
C10B H10D 0.9600 . ?
C10B H10E 0.9600 . ?
C10B H10F 0.9600 . ?
S1C O1C 1.4438(18) . ?
S1C O2C 1.4426(18) . ?
S1C N1C 1.614(2) . ?
S1C C4C 1.770(2) . ?
N1C C1C 1.328(3) . ?
N2C C1C 1.313(3) . ?
N2C C2C 1.461(3) . ?
N2C C3C 1.462(3) . ?
C1C H1C 0.9300 . ?
C2C H2CA 0.9600 . ?
C2C H2CB 0.9600 . ?
C2C H2CC 0.9600 . ?
C3C H3CA 0.9600 . ?
C3C H3CB 0.9600 . ?
C3C H3CC 0.9600 . ?
C4C C5C 1.391(3) . ?
C4C C9C 1.391(3) . ?
C5C H5C 0.9300 . ?
C5C C6C 1.386(4) . ?
C6C H6C 0.9300 . ?
C6C C7C 1.396(4) . ?
C7C C8C 1.388(4) . ?
C7C C10C 1.506(4) . ?
C8C H8C 0.9300 . ?
C8C C9C 1.387(4) . ?
C9C H9C 0.9300 . ?
C10C H10G 0.9600 . ?
C10C H10H 0.9600 . ?
C10C H10I 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
O1A S1A N1A 106.87(11) . . ?
O1A S1A C4A 106.80(11) . . ?
O2A S1A O1A 117.46(11) . . ?
O2A S1A N1A 112.18(11) . . ?
O2A S1A C4A 107.33(11) . . ?
N1A S1A C4A 105.45(11) . . ?
C1A N1A S1A 115.69(17) . . ?
C1A N2A C2A 121.8(2) . . ?
C1A N2A C3A 121.3(2) . . ?
C2A N2A C3A 116.8(2) . . ?
N1A C1A H1A 118.9 . . ?
N2A C1A N1A 122.3(2) . . ?
N2A C1A H1A 118.9 . . ?
N2A C2A H2AA 109.5 . . ?
N2A C2A H2AB 109.5 . . ?
N2A C2A H2AC 109.5 . . ?
H2AA C2A H2AB 109.5 . . ?
H2AA C2A H2AC 109.5 . . ?
H2AB C2A H2AC 109.5 . . ?
N2A C3A H3AA 109.5 . . ?
N2A C3A H3AB 109.5 . . ?
N2A C3A H3AC 109.5 . . ?
H3AA C3A H3AB 109.5 . . ?
H3AA C3A H3AC 109.5 . . ?
H3AB C3A H3AC 109.5 . . ?
C5A C4A S1A 120.02(19) . . ?
C5A C4A C9A 120.7(2) . . ?
C9A C4A S1A 119.29(19) . . ?
C4A C5A H5A 120.5 . . ?
C4A C5A C6A 119.1(2) . . ?
C6A C5A H5A 120.5 . . ?
C5A C6A H6A 119.4 . . ?
C5A C6A C7A 121.2(2) . . ?
C7A C6A H6A 119.4 . . ?
C6A C7A C8A 118.8(2) . . ?
C6A C7A C10A 120.6(2) . . ?
C8A C7A C10A 120.6(2) . . ?
C7A C8A H8A 119.6 . . ?
C9A C8A C7A 120.8(2) . . ?
C9A C8A H8A 119.6 . . ?
C4A C9A H9A 120.3 . . ?
C8A C9A C4A 119.4(2) . . ?
C8A C9A H9A 120.3 . . ?
C7A C10A H10A 109.5 . . ?
C7A C10A H10B 109.5 . . ?
C7A C10A H10C 109.5 . . ?
H10A C10A H10B 109.5 . . ?
H10A C10A H10C 109.5 . . ?
H10B C10A H10C 109.5 . . ?
O1B S1B O2B 117.42(11) . . ?
O1B S1B N1B 106.67(11) . . ?
O1B S1B C4B 107.78(11) . . ?
O2B S1B N1B 113.00(11) . . ?
O2B S1B C4B 107.81(11) . . ?
N1B S1B C4B 103.12(11) . . ?
C1B N1B S1B 116.04(17) . . ?
C1B N2B C2B 121.0(2) . . ?
C1B N2B C3B 121.0(2) . . ?
C2B N2B C3B 118.0(2) . . ?
N1B C1B H1B 119.6 . . ?
N2B C1B N1B 120.8(2) . . ?
N2B C1B H1B 119.6 . . ?
N2B C2B H2BA 109.5 . . ?
N2B C2B H2BB 109.5 . . ?
N2B C2B H2BC 109.5 . . ?
H2BA C2B H2BB 109.5 . . ?
H2BA C2B H2BC 109.5 . . ?
H2BB C2B H2BC 109.5 . . ?
N2B C3B H3BA 109.5 . . ?
N2B C3B H3BB 109.5 . . ?
N2B C3B H3BC 109.5 . . ?
H3BA C3B H3BB 109.5 . . ?
H3BA C3B H3BC 109.5 . . ?
H3BB C3B H3BC 109.5 . . ?
C5B C4B S1B 119.20(19) . . ?
C9B C4B S1B 120.02(19) . . ?
C9B C4B C5B 120.6(2) . . ?
C4B C5B H5B 120.6 . . ?
C6B C5B C4B 118.8(2) . . ?
C6B C5B H5B 120.6 . . ?
C5B C6B H6B 119.2 . . ?
C5B C6B C7B 121.5(2) . . ?
C7B C6B H6B 119.2 . . ?
C6B C7B C10B 120.2(2) . . ?
C8B C7B C6B 118.5(2) . . ?
C8B C7B C10B 121.3(2) . . ?
C7B C8B H8B 119.7 . . ?
C9B C8B C7B 120.6(2) . . ?
C9B C8B H8B 119.7 . . ?
C4B C9B C8B 119.9(2) . . ?
C4B C9B H9B 120.0 . . ?
C8B C9B H9B 120.0 . . ?
C7B C10B H10D 109.5 . . ?
C7B C10B H10E 109.5 . . ?
C7B C10B H10F 109.5 . . ?
H10D C10B H10E 109.5 . . ?
H10D C10B H10F 109.5 . . ?
H10E C10B H10F 109.5 . . ?
O1C S1C N1C 106.58(11) . . ?
O1C S1C C4C 106.74(11) . . ?
O2C S1C O1C 117.57(11) . . ?
O2C S1C N1C 111.78(11) . . ?
O2C S1C C4C 106.30(11) . . ?
N1C S1C C4C 107.36(11) . . ?
C1C N1C S1C 115.50(17) . . ?
C1C N2C C2C 121.3(2) . . ?
C1C N2C C3C 121.9(2) . . ?
C2C N2C C3C 116.7(2) . . ?
N1C C1C H1C 119.1 . . ?
N2C C1C N1C 121.7(2) . . ?
N2C C1C H1C 119.1 . . ?
N2C C2C H2CA 109.5 . . ?
N2C C2C H2CB 109.5 . . ?
N2C C2C H2CC 109.5 . . ?
H2CA C2C H2CB 109.5 . . ?
H2CA C2C H2CC 109.5 . . ?
H2CB C2C H2CC 109.5 . . ?
N2C C3C H3CA 109.5 . . ?
N2C C3C H3CB 109.5 . . ?
N2C C3C H3CC 109.5 . . ?
H3CA C3C H3CB 109.5 . . ?
H3CA C3C H3CC 109.5 . . ?
H3CB C3C H3CC 109.5 . . ?
C5C C4C S1C 120.00(19) . . ?
C9C C4C S1C 119.75(19) . . ?
C9C C4C C5C 120.2(2) . . ?
C4C C5C H5C 120.4 . . ?
C6C C5C C4C 119.2(2) . . ?
C6C C5C H5C 120.4 . . ?
C5C C6C H6C 119.2 . . ?
C5C C6C C7C 121.5(2) . . ?
C7C C6C H6C 119.2 . . ?
C6C C7C C10C 120.6(2) . . ?
C8C C7C C6C 118.1(2) . . ?
C8C C7C C10C 121.3(2) . . ?
C7C C8C H8C 119.3 . . ?
C9C C8C C7C 121.4(2) . . ?
C9C C8C H8C 119.3 . . ?
C4C C9C H9C 120.2 . . ?
C8C C9C C4C 119.6(2) . . ?
C8C C9C H9C 120.2 . . ?
C7C C10C H10G 109.5 . . ?
C7C C10C H10H 109.5 . . ?
C7C C10C H10I 109.5 . . ?
H10G C10C H10H 109.5 . . ?
H10G C10C H10I 109.5 . . ?
H10H C10C H10I 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
S1A N1A C1A N2A -179.22(18) . . . . ?
S1A C4A C5A C6A -179.87(19) . . . . ?
S1A C4A C9A C8A -179.66(19) . . . . ?
O1A S1A N1A C1A -155.74(18) . . . . ?
O1A S1A C4A C5A 147.0(2) . . . . ?
O1A S1A C4A C9A -33.1(2) . . . . ?
O2A S1A N1A C1A -25.7(2) . . . . ?
O2A S1A C4A C5A 20.2(2) . . . . ?
O2A S1A C4A C9A -159.84(19) . . . . ?
N1A S1A C4A C5A -99.6(2) . . . . ?
N1A S1A C4A C9A 80.4(2) . . . . ?
C2A N2A C1A N1A -177.1(2) . . . . ?
C3A N2A C1A N1A -1.2(4) . . . . ?
C4A S1A N1A C1A 90.9(2) . . . . ?
C4A C5A C6A C7A -1.0(4) . . . . ?
C5A C4A C9A C8A 0.3(4) . . . . ?
C5A C6A C7A C8A 1.3(4) . . . . ?
C5A C6A C7A C10A -179.0(2) . . . . ?
C6A C7A C8A C9A -0.8(4) . . . . ?
C7A C8A C9A C4A 0.0(4) . . . . ?
C9A C4A C5A C6A 0.2(4) . . . . ?
C10A C7A C8A C9A 179.5(2) . . . . ?
S1B N1B C1B N2B 169.34(18) . . . . ?
S1B C4B C5B C6B -174.6(2) . . . . ?
S1B C4B C9B C8B 174.7(2) . . . . ?
O1B S1B N1B C1B 159.01(18) . . . . ?
O1B S1B C4B C5B -160.8(2) . . . . ?
O1B S1B C4B C9B 24.0(2) . . . . ?
O2B S1B N1B C1B 28.5(2) . . . . ?
O2B S1B C4B C5B -33.1(2) . . . . ?
O2B S1B C4B C9B 151.7(2) . . . . ?
N1B S1B C4B C5B 86.6(2) . . . . ?
N1B S1B C4B C9B -88.6(2) . . . . ?
C2B N2B C1B N1B 176.1(2) . . . . ?
C3B N2B C1B N1B -2.2(3) . . . . ?
C4B S1B N1B C1B -87.6(2) . . . . ?
C4B C5B C6B C7B 0.0(4) . . . . ?
C5B C4B C9B C8B -0.5(4) . . . . ?
C5B C6B C7B C8B -0.7(4) . . . . ?
C5B C6B C7B C10B 179.6(2) . . . . ?
C6B C7B C8B C9B 0.8(4) . . . . ?
C7B C8B C9B C4B -0.2(4) . . . . ?
C9B C4B C5B C6B 0.6(4) . . . . ?
C10B C7B C8B C9B -179.5(2) . . . . ?
S1C N1C C1C N2C -175.78(18) . . . . ?
S1C C4C C5C C6C 177.12(19) . . . . ?
S1C C4C C9C C8C -176.6(2) . . . . ?
O1C S1C N1C C1C 155.81(18) . . . . ?
O1C S1C C4C C5C -156.7(2) . . . . ?
O1C S1C C4C C9C 20.0(2) . . . . ?
O2C S1C N1C C1C 26.1(2) . . . . ?
O2C S1C C4C C5C -30.5(2) . . . . ?
O2C S1C C4C C9C 146.3(2) . . . . ?
N1C S1C C4C C5C 89.3(2) . . . . ?
N1C S1C C4C C9C -94.0(2) . . . . ?
C2C N2C C1C N1C 179.3(2) . . . . ?
C3C N2C C1C N1C 3.6(4) . . . . ?
C4C S1C N1C C1C -90.1(2) . . . . ?
C4C C5C C6C C7C -0.9(4) . . . . ?
C5C C4C C9C C8C 0.2(4) . . . . ?
C5C C6C C7C C8C 0.9(4) . . . . ?
C5C C6C C7C C10C 180.0(2) . . . . ?
C6C C7C C8C C9C -0.3(4) . . . . ?
C7C C8C C9C C4C -0.2(4) . . . . ?
C9C C4C C5C C6C 0.4(4) . . . . ?
C10C C7C C8C C9C -179.4(3) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.768
_oxdiff_exptl_absorpt_empirical_full_min 0.772
####################################################################### 
# 
# 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_23e
_database_code_depnum_ccdc_archive 'CCDC 2051042'
loop_
_audit_author_name
_audit_author_address
'Felix Hennersdorf'
;TU Dresden
Germany
;
_audit_update_record             
;
2020-12-17 deposited with the CCDC.	2021-04-01 downloaded from the CCDC.
;
_audit_creation_date             2018-04-18
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C9 H11 F N2 O2 S'
_chemical_formula_sum            'C9 H11 F N2 O2 S'
_chemical_formula_weight         230.26
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C72 H88 F8 N16 O16 S8 '
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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                   13.0075(5)
_cell_length_b                   13.3299(5)
_cell_length_c                   11.8029(4)
_cell_angle_alpha                90
_cell_angle_beta                 91.320(3)
_cell_angle_gamma                90
_cell_volume                     2045.96(12)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    4643
_cell_measurement_temperature    100.3(7)
_cell_measurement_theta_max      76.1950
_cell_measurement_theta_min      3.3700
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.830
_exptl_absorpt_correction_T_max  0.897
_exptl_absorpt_correction_T_min  0.633
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.495
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             960
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 9 1 0.0565
-1 0 -8 0.1312
0 -6 5 0.1167
1 6 5 0.0832
-8 0 0 0.0217
8 0 0 0.0217
-6 3 5 0.0918
-7 -5 0 0.0308
1 -9 0 0.0515
7 -5 0 0.0382
5 7 0 0.0548
-1 9 0 0.0638
-8 3 1 0.0255

_exptl_crystal_size_max          0.283
_exptl_crystal_size_mid          0.117
_exptl_crystal_size_min          0.043
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0.0034 8.9975 0.9952 0.1632 0.8663 0.5667
-0.9770 -0.0057 -7.9808 0.0760 0.4477 -0.9479
-0.0176 -5.9945 4.9919 -0.2434 -0.8740 0.2848
0.9892 6.0016 4.9850 0.1199 0.3217 0.8969
-7.9892 -0.0023 0.0251 -0.9118 0.2333 -0.0990
7.9892 0.0023 -0.0251 0.9118 -0.2333 0.0990
-6.0033 3.0006 5.0079 -0.7403 0.2196 0.6603
-6.9939 -5.0003 0.0235 -0.9017 -0.3062 -0.3365
0.9925 -8.9966 -0.0003 -0.0730 -0.9478 -0.4374
6.9871 -4.9962 -0.0204 0.6940 -0.7144 -0.1632
4.9980 6.9990 -0.0179 0.7153 0.5687 0.4117
-0.9925 8.9966 0.0003 0.0730 0.9478 0.4374
-7.9898 2.9973 1.0221 -0.8732 0.4871 0.1678

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0389
_diffrn_reflns_av_unetI/netI     0.0416
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            10625
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.808
_diffrn_reflns_theta_min         3.399
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.3(7)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2850
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     21.00  65.00   0.50    0.75    --   42.25  38.00 120.00   88
  2  ω     90.00 115.00   0.50    0.75    --   42.25  38.00 120.00   50
  3  ω     91.00 169.00   0.50    3.00    --  111.00  30.00  90.00  156
  4  ω    153.00 178.00   0.50    3.00    --  111.00  45.00  90.00   50
  5  ω    134.00 166.00   0.50    3.00    --  111.00  61.00  30.00   64
  6  ω    151.00 178.00   0.50    3.00    --  111.00 125.00  30.00   54
  7  ω    119.00 146.00   0.50    3.00    --  111.00 125.00  30.00   54
  8  ω    102.00 129.00   0.50    3.00    --  111.00  61.00  30.00   54
  9  ω     96.00 123.00   0.50    3.00    --  111.00  45.00  90.00   54
 10  ω    101.00 155.00   0.50    3.00    --  111.00  89.00 -43.00  108
 11  ω     95.00 177.00   0.50    3.00    --  111.00 125.00 -90.00  164
 12  ω    109.00 134.00   0.50    3.00    --  111.00 -45.00-150.00   50
 13  ω     58.00 118.00   0.50    3.00    --  111.00-125.00-120.00  120
 14  ω     46.00  74.00   0.50    0.75    --   42.25-125.00 -60.00   56
 15  ω      1.00  40.00   0.50    0.75    --   42.25 -99.00 -30.00   78
 16  ω     36.00  76.00   0.50    3.00    --  111.00 -94.00 -30.00   80
 17  ω     48.00  97.00   0.50    3.00    --  111.00-125.00 -30.00   98
 18  ω     41.00  79.00   0.50    3.00    --  111.00 -45.00-150.00   76
 19  ω     34.00  67.00   0.50    3.00    --  111.00 -94.00-180.00   66
 20  ω     38.00  96.00   0.50    0.75    --   42.25-125.00 150.00  116
 21  ω   -110.00 -19.00   0.50    0.75    --  -38.50 -38.00 120.00  182
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1140512000
_diffrn_orient_matrix_UB_12      0.0206975000
_diffrn_orient_matrix_UB_13      -0.0235005000
_diffrn_orient_matrix_UB_21      -0.0293908000
_diffrn_orient_matrix_UB_22      0.1021071000
_diffrn_orient_matrix_UB_23      -0.0525667000
_diffrn_orient_matrix_UB_31      0.0127482000
_diffrn_orient_matrix_UB_32      0.0500223000
_diffrn_orient_matrix_UB_33      0.1171719000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3826
_reflns_number_total             4243
_reflns_odcompleteness_completeness 99.61
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_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 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_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         0.407
_refine_diff_density_min         -0.478
_refine_diff_density_rms         0.084
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.122
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     275
_refine_ls_number_reflns         4243
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0610
_refine_ls_R_factor_gt           0.0569
_refine_ls_restrained_S_all      1.122
_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)+(0.0497P)²+5.0163P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1536
_refine_ls_wR_factor_ref         0.1561
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3A(H3A), C4A(H4A), C5A(H5A), C6A(H6A), C7A(H7A), C3B(H3B), C4B(H4B),
 C5B(H5B), C6B(H6B), C7B(H7B)
2.b Idealised Me refined as rotating group:
 C8A(H8AA,H8AB,H8AC), C9A(H9AA,H9AB,H9AC), C8B(H8BA,H8BB,H8BC), C9B(H9BA,H9BB,
 H9BC)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1A S 0.63846(6) 0.22195(5) 0.34420(7) 0.0237(2) Uani 1 1 d . . . . .
F1A F 0.52579(15) 0.37656(15) 0.47789(15) 0.0289(4) Uani 1 1 d . . . . .
O1A O 0.6622(2) 0.15919(19) 0.2489(2) 0.0353(6) Uani 1 1 d . . . . .
O2A O 0.61520(19) 0.17313(18) 0.4495(2) 0.0299(5) Uani 1 1 d . . . . .
N1A N 0.7293(2) 0.3044(2) 0.3577(2) 0.0246(5) Uani 1 1 d . . . . .
N2A N 0.8236(2) 0.4013(2) 0.4840(2) 0.0245(5) Uani 1 1 d . . . . .
C1A C 0.5290(2) 0.2931(2) 0.3013(3) 0.0222(6) Uani 1 1 d . . . . .
C2A C 0.4823(2) 0.3608(2) 0.3739(3) 0.0234(6) Uani 1 1 d . . . . .
C3A C 0.3955(3) 0.4142(3) 0.3433(3) 0.0308(7) Uani 1 1 d . . . . .
H3A H 0.3664 0.4594 0.3933 0.037 Uiso 1 1 calc R . . . .
C4A C 0.3528(3) 0.3991(3) 0.2363(3) 0.0351(8) Uani 1 1 d . . . . .
H4A H 0.2934 0.4335 0.2145 0.042 Uiso 1 1 calc R . . . .
C5A C 0.3978(3) 0.3328(3) 0.1612(3) 0.0340(8) Uani 1 1 d . . . . .
H5A H 0.3686 0.3232 0.0893 0.041 Uiso 1 1 calc R . . . .
C6A C 0.4865(3) 0.2808(2) 0.1934(3) 0.0274(7) Uani 1 1 d . . . . .
H6A H 0.5175 0.2377 0.1424 0.033 Uiso 1 1 calc R . . . .
C7A C 0.7539(2) 0.3313(2) 0.4622(3) 0.0233(6) Uani 1 1 d . . . . .
H7A H 0.7214 0.3003 0.5222 0.028 Uiso 1 1 calc R . . . .
C8A C 0.8812(3) 0.4484(3) 0.3939(3) 0.0286(7) Uani 1 1 d . . . . .
H8AA H 0.9455 0.4141 0.3855 0.043 Uiso 1 1 calc GR . . . .
H8AB H 0.8940 0.5174 0.4128 0.043 Uiso 1 1 calc GR . . . .
H8AC H 0.8421 0.4448 0.3241 0.043 Uiso 1 1 calc GR . . . .
C9A C 0.8537(3) 0.4275(3) 0.6001(3) 0.0296(7) Uani 1 1 d . . . . .
H9AA H 0.8090 0.3943 0.6518 0.044 Uiso 1 1 calc GR . . . .
H9AB H 0.8484 0.4988 0.6100 0.044 Uiso 1 1 calc GR . . . .
H9AC H 0.9233 0.4067 0.6149 0.044 Uiso 1 1 calc GR . . . .
S1B S 0.84748(6) 0.75499(6) 0.06718(6) 0.02296(19) Uani 1 1 d . . . . .
F1B F 0.95966(16) 0.60355(16) 0.20762(17) 0.0343(5) Uani 1 1 d . . . . .
O1B O 0.87244(18) 0.80850(17) 0.17040(19) 0.0269(5) Uani 1 1 d . . . . .
O2B O 0.8201(2) 0.8146(2) -0.0310(2) 0.0347(6) Uani 1 1 d . . . . .
N1B N 0.7598(2) 0.6711(2) 0.0820(2) 0.0238(5) Uani 1 1 d . . . . .
N2B N 0.6643(2) 0.5812(2) 0.2091(2) 0.0235(5) Uani 1 1 d . . . . .
C1B C 0.9581(2) 0.6862(2) 0.0308(3) 0.0254(6) Uani 1 1 d . . . . .
C2B C 1.0043(3) 0.6194(3) 0.1072(3) 0.0283(7) Uani 1 1 d . . . . .
C3B C 1.0937(3) 0.5686(3) 0.0838(4) 0.0407(9) Uani 1 1 d . . . . .
H3B H 1.1227 0.5235 0.1355 0.049 Uiso 1 1 calc R . . . .
C4B C 1.1385(3) 0.5872(3) -0.0192(4) 0.0484(11) Uani 1 1 d . . . . .
H4B H 1.1997 0.5551 -0.0362 0.058 Uiso 1 1 calc R . . . .
C5B C 1.0946(3) 0.6520(4) -0.0975(4) 0.0458(11) Uani 1 1 d . . . . .
H5B H 1.1263 0.6632 -0.1662 0.055 Uiso 1 1 calc R . . . .
C6B C 1.0028(3) 0.7008(3) -0.0736(3) 0.0346(8) Uani 1 1 d . . . . .
H6B H 0.9717 0.7428 -0.1272 0.042 Uiso 1 1 calc R . . . .
C7B C 0.7343(2) 0.6504(2) 0.1861(3) 0.0219(6) Uani 1 1 d . . . . .
H7B H 0.7660 0.6851 0.2457 0.026 Uiso 1 1 calc R . . . .
C8B C 0.6075(3) 0.5263(3) 0.1211(3) 0.0291(7) Uani 1 1 d . . . . .
H8BA H 0.5360 0.5441 0.1232 0.044 Uiso 1 1 calc GR . . . .
H8BB H 0.6149 0.4555 0.1340 0.044 Uiso 1 1 calc GR . . . .
H8BC H 0.6340 0.5431 0.0483 0.044 Uiso 1 1 calc GR . . . .
C9B C 0.6364(3) 0.5604(3) 0.3255(3) 0.0274(7) Uani 1 1 d . . . . .
H9BA H 0.6762 0.6023 0.3760 0.041 Uiso 1 1 calc GR . . . .
H9BB H 0.6501 0.4912 0.3426 0.041 Uiso 1 1 calc GR . . . .
H9BC H 0.5646 0.5740 0.3345 0.041 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1A O1A 1.441(2) . ?
S1A O2A 1.441(2) . ?
S1A N1A 1.619(3) . ?
S1A C1A 1.774(3) . ?
F1A C2A 1.356(4) . ?
N1A C7A 1.316(4) . ?
N2A C7A 1.322(4) . ?
N2A C8A 1.457(4) . ?
N2A C9A 1.459(4) . ?
C1A C2A 1.394(4) . ?
C1A C6A 1.387(4) . ?
C2A C3A 1.375(5) . ?
C3A H3A 0.9300 . ?
C3A C4A 1.383(5) . ?
C4A H4A 0.9300 . ?
C4A C5A 1.391(6) . ?
C5A H5A 0.9300 . ?
C5A C6A 1.392(5) . ?
C6A H6A 0.9300 . ?
C7A H7A 0.9300 . ?
C8A H8AA 0.9600 . ?
C8A H8AB 0.9600 . ?
C8A H8AC 0.9600 . ?
C9A H9AA 0.9600 . ?
C9A H9AB 0.9600 . ?
C9A H9AC 0.9600 . ?
S1B O1B 1.442(2) . ?
S1B O2B 1.444(2) . ?
S1B N1B 1.609(3) . ?
S1B C1B 1.768(3) . ?
F1B C2B 1.349(4) . ?
N1B C7B 1.310(4) . ?
N2B C7B 1.329(4) . ?
N2B C8B 1.458(4) . ?
N2B C9B 1.455(4) . ?
C1B C2B 1.392(5) . ?
C1B C6B 1.389(5) . ?
C2B C3B 1.379(5) . ?
C3B H3B 0.9300 . ?
C3B C4B 1.383(7) . ?
C4B H4B 0.9300 . ?
C4B C5B 1.379(7) . ?
C5B H5B 0.9300 . ?
C5B C6B 1.395(6) . ?
C6B H6B 0.9300 . ?
C7B H7B 0.9300 . ?
C8B H8BA 0.9600 . ?
C8B H8BB 0.9600 . ?
C8B H8BC 0.9600 . ?
C9B H9BA 0.9600 . ?
C9B H9BB 0.9600 . ?
C9B H9BC 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
O1A S1A O2A 117.65(16) . . ?
O1A S1A N1A 107.59(15) . . ?
O1A S1A C1A 105.81(15) . . ?
O2A S1A N1A 112.87(14) . . ?
O2A S1A C1A 107.70(14) . . ?
N1A S1A C1A 104.15(14) . . ?
C7A N1A S1A 116.0(2) . . ?
C7A N2A C8A 121.6(3) . . ?
C7A N2A C9A 121.3(3) . . ?
C8A N2A C9A 116.8(3) . . ?
C2A C1A S1A 122.0(2) . . ?
C6A C1A S1A 119.9(3) . . ?
C6A C1A C2A 118.1(3) . . ?
F1A C2A C1A 118.5(3) . . ?
F1A C2A C3A 118.7(3) . . ?
C3A C2A C1A 122.7(3) . . ?
C2A C3A H3A 120.8 . . ?
C2A C3A C4A 118.3(3) . . ?
C4A C3A H3A 120.8 . . ?
C3A C4A H4A 119.7 . . ?
C3A C4A C5A 120.6(3) . . ?
C5A C4A H4A 119.7 . . ?
C4A C5A H5A 120.0 . . ?
C4A C5A C6A 120.1(3) . . ?
C6A C5A H5A 120.0 . . ?
C1A C6A C5A 120.2(3) . . ?
C1A C6A H6A 119.9 . . ?
C5A C6A H6A 119.9 . . ?
N1A C7A N2A 121.7(3) . . ?
N1A C7A H7A 119.2 . . ?
N2A C7A H7A 119.2 . . ?
N2A C8A H8AA 109.5 . . ?
N2A C8A H8AB 109.5 . . ?
N2A C8A H8AC 109.5 . . ?
H8AA C8A H8AB 109.5 . . ?
H8AA C8A H8AC 109.5 . . ?
H8AB C8A H8AC 109.5 . . ?
N2A C9A H9AA 109.5 . . ?
N2A C9A H9AB 109.5 . . ?
N2A C9A H9AC 109.5 . . ?
H9AA C9A H9AB 109.5 . . ?
H9AA C9A H9AC 109.5 . . ?
H9AB C9A H9AC 109.5 . . ?
O1B S1B O2B 116.92(15) . . ?
O1B S1B N1B 113.46(14) . . ?
O1B S1B C1B 107.03(15) . . ?
O2B S1B N1B 107.88(15) . . ?
O2B S1B C1B 106.16(16) . . ?
N1B S1B C1B 104.41(15) . . ?
C7B N1B S1B 116.3(2) . . ?
C7B N2B C8B 122.8(3) . . ?
C7B N2B C9B 120.8(3) . . ?
C9B N2B C8B 116.3(3) . . ?
C2B C1B S1B 121.0(3) . . ?
C6B C1B S1B 120.1(3) . . ?
C6B C1B C2B 118.8(3) . . ?
F1B C2B C1B 118.8(3) . . ?
F1B C2B C3B 118.7(3) . . ?
C3B C2B C1B 122.5(4) . . ?
C2B C3B H3B 121.3 . . ?
C2B C3B C4B 117.5(4) . . ?
C4B C3B H3B 121.3 . . ?
C3B C4B H4B 119.2 . . ?
C5B C4B C3B 121.7(4) . . ?
C5B C4B H4B 119.2 . . ?
C4B C5B H5B 120.0 . . ?
C4B C5B C6B 120.0(4) . . ?
C6B C5B H5B 120.0 . . ?
C1B C6B C5B 119.4(4) . . ?
C1B C6B H6B 120.3 . . ?
C5B C6B H6B 120.3 . . ?
N1B C7B N2B 121.8(3) . . ?
N1B C7B H7B 119.1 . . ?
N2B C7B H7B 119.1 . . ?
N2B C8B H8BA 109.5 . . ?
N2B C8B H8BB 109.5 . . ?
N2B C8B H8BC 109.5 . . ?
H8BA C8B H8BB 109.5 . . ?
H8BA C8B H8BC 109.5 . . ?
H8BB C8B H8BC 109.5 . . ?
N2B C9B H9BA 109.5 . . ?
N2B C9B H9BB 109.5 . . ?
N2B C9B H9BC 109.5 . . ?
H9BA C9B H9BB 109.5 . . ?
H9BA C9B H9BC 109.5 . . ?
H9BB C9B H9BC 109.5 . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.488
_oxdiff_exptl_absorpt_empirical_full_min 0.700
####################################################################### 
# 
# 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_25
_database_code_depnum_ccdc_archive 'CCDC 2051049'
loop_
_audit_author_name
_audit_author_address
'Felix Hennersdorf'
;TU Dresden
Germany
;
_audit_update_record             
;
2020-12-17 deposited with the CCDC.	2021-04-01 downloaded from the CCDC.
;
_audit_creation_date             2016-05-31
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H13 N O4 S2'
_chemical_formula_sum            'C13 H13 N O4 S2'
_chemical_formula_weight         311.36
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C52 H52 N4 O16 S8 '
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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                   10.92417(13)
_cell_length_b                   8.34450(8)
_cell_length_c                   15.03139(17)
_cell_angle_alpha                90
_cell_angle_beta                 103.0225(12)
_cell_angle_gamma                90
_cell_volume                     1334.97(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5268
_cell_measurement_temperature    99.97(10)
_cell_measurement_theta_max      76.2320
_cell_measurement_theta_min      4.5350
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    3.747
_exptl_absorpt_correction_T_max  0.742
_exptl_absorpt_correction_T_min  0.501
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.549
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             648
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 0 1 0.0464
-1 0 -1 0.0504
1 0 -1 0.0725
0 1 -2 0.0996
0 -1 -2 0.0984
0 0 -1 0.0923
-4 0 9 0.0475
-7 -2 3 0.0838
-3 -5 3 0.1869

_exptl_crystal_size_max          0.427
_exptl_crystal_size_mid          0.147
_exptl_crystal_size_min          0.097
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0.9979 0.0008 1.0012 -0.0916 0.1746 0.0034
-0.9979 -0.0008 -1.0012 0.0916 -0.1746 -0.0034
1.0002 -0.0003 -0.9983 0.1044 0.1120 -0.0410
0.0013 0.9985 -2.0009 0.1490 -0.0838 -0.2214
0.0033 -1.0006 -1.9981 0.2430 -0.0414 0.1326
0.0012 -0.0005 -0.9998 0.0980 -0.0313 -0.0222
-4.0068 0.0039 8.9921 -0.9078 -0.2914 0.2751
-6.9949 -1.9991 2.9921 -0.2450 -0.8665 0.5524
-2.9956 -4.9968 3.0021 -0.0781 -0.2298 1.0081

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0185
_diffrn_reflns_av_unetI/netI     0.0205
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            6529
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.508
_diffrn_reflns_theta_min         4.552
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.97(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2850
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -63.00  32.00   0.50    0.50    --  -38.50  57.00 -30.00  190
  2  ω     63.00  97.00   0.50    0.50    --   42.75-125.00-180.00   68
  3  ω     68.00  98.00   0.50    2.00    --  111.00 -94.00 -30.00   60
  4  ω     53.00  80.00   0.50    2.00    --  111.00 -94.00  30.00   54
  5  ω     42.00 108.00   0.50    2.00    --  111.00 -94.00   0.00  132
  6  ω     41.00 114.00   0.50    2.00    --  111.00 -61.00 120.00  146
  7  ω     41.00 139.00   0.50    2.00    --  111.00 -61.00   0.00  196
  8  ω     92.00 178.00   0.50    2.00    --  111.00  30.00 -60.00  172
  9  ω     99.00 126.00   0.50    2.00    --  111.00 125.00 -60.00   54
 10  ω     36.00 132.00   0.50    2.00    --  111.00 -30.00 120.00  192
 11  ω     38.00 114.00   0.50    2.00    --  111.00 -30.00   0.00  152
 12  ω   -110.00 -23.00   0.50    0.50    --  -38.50 -77.00-150.00  174
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0065931000
_diffrn_orient_matrix_UB_12      -0.0471995000
_diffrn_orient_matrix_UB_13      -0.0979928000
_diffrn_orient_matrix_UB_21      0.1433571000
_diffrn_orient_matrix_UB_22      -0.0210305000
_diffrn_orient_matrix_UB_23      0.0314857000
_diffrn_orient_matrix_UB_31      -0.0188291000
_diffrn_orient_matrix_UB_32      -0.1770806000
_diffrn_orient_matrix_UB_33      0.0222797000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2732
_reflns_number_total             2778
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_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         0.477
_refine_diff_density_min         -0.595
_refine_diff_density_rms         0.069
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.112
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     233
_refine_ls_number_reflns         2778
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0353
_refine_ls_R_factor_gt           0.0348
_refine_ls_restrained_S_all      1.112
_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)+(0.0404P)²+1.1201P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0879
_refine_ls_wR_factor_ref         0.0883
_refine_special_details          ?
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.51995(4) 0.29645(5) 0.66836(3) 0.01562(12) Uani 1 1 d . . . . .
S2 S 0.34297(4) 0.52442(5) 0.72077(3) 0.01948(12) Uani 1 1 d . . . . .
O2 O 0.57210(11) 0.43604(15) 0.63596(9) 0.0195(3) Uani 1 1 d . . . . .
O1 O 0.60178(12) 0.18036(16) 0.72139(9) 0.0228(3) Uani 1 1 d . . . . .
O3 O 0.32797(13) 0.56943(17) 0.62734(9) 0.0255(3) Uani 1 1 d . . . . .
O4 O 0.23503(13) 0.49560(19) 0.75779(10) 0.0294(3) Uani 1 1 d . . . . .
N1 N 0.42423(14) 0.35352(19) 0.73594(10) 0.0198(3) Uani 1 1 d . . . . .
C1 C 0.42136(15) 0.1980(2) 0.57580(11) 0.0154(3) Uani 1 1 d . . . . .
C2 C 0.39970(16) 0.0350(2) 0.58340(12) 0.0178(3) Uani 1 1 d . . . . .
C6 C 0.37024(16) 0.2844(2) 0.49697(12) 0.0181(3) Uani 1 1 d . . . . .
C5 C 0.29379(17) 0.2036(2) 0.42420(12) 0.0224(4) Uani 1 1 d . . . . .
C7 C 0.44020(16) 0.6634(2) 0.79225(12) 0.0187(3) Uani 1 1 d . . . . .
C3 C 0.32382(17) -0.0439(2) 0.50996(13) 0.0220(4) Uani 1 1 d . . . . .
C12 C 0.53783(17) 0.7362(2) 0.76176(13) 0.0221(4) Uani 1 1 d . . . . .
C4 C 0.27090(17) 0.0407(2) 0.43075(13) 0.0232(4) Uani 1 1 d . . . . .
C9 C 0.4979(2) 0.8015(2) 0.93434(14) 0.0295(4) Uani 1 1 d . . . . .
C11 C 0.61630(18) 0.8416(2) 0.81905(15) 0.0270(4) Uani 1 1 d . . . . .
C10 C 0.59698(19) 0.8733(2) 0.90558(15) 0.0292(4) Uani 1 1 d . . . . .
C8 C 0.41860(19) 0.6949(2) 0.87806(13) 0.0242(4) Uani 1 1 d . . . . .
C13 C 0.4430(2) 0.2807(3) 0.82794(13) 0.0293(4) Uani 1 1 d . . . . .
H2 H 0.434(2) -0.019(3) 0.6353(17) 0.025(6) Uiso 1 1 d . . . . .
H6 H 0.390(2) 0.396(3) 0.4956(15) 0.021(5) Uiso 1 1 d . . . . .
H3 H 0.307(2) -0.157(3) 0.5155(17) 0.028(6) Uiso 1 1 d . . . . .
H8 H 0.353(3) 0.644(3) 0.8971(17) 0.031(6) Uiso 1 1 d . . . . .
H4 H 0.221(2) -0.015(3) 0.3790(17) 0.028(6) Uiso 1 1 d . . . . .
H5 H 0.259(2) 0.262(3) 0.3693(17) 0.029(6) Uiso 1 1 d . . . . .
H9 H 0.481(3) 0.826(3) 0.995(2) 0.040(7) Uiso 1 1 d . . . . .
H11 H 0.683(2) 0.890(3) 0.7990(17) 0.029(6) Uiso 1 1 d . . . . .
H13A H 0.519(2) 0.333(3) 0.8720(17) 0.028(6) Uiso 1 1 d . . . . .
H10 H 0.652(3) 0.944(3) 0.9473(18) 0.035(7) Uiso 1 1 d . . . . .
H12 H 0.549(2) 0.714(3) 0.6982(17) 0.024(6) Uiso 1 1 d . . . . .
H13B H 0.364(3) 0.308(3) 0.8457(19) 0.038(7) Uiso 1 1 d . . . . .
H13C H 0.454(3) 0.156(4) 0.820(2) 0.056(9) 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 O2 1.4295(13) . ?
S1 O1 1.4324(13) . ?
S1 N1 1.6826(15) . ?
S1 C1 1.7593(17) . ?
S2 O3 1.4271(13) . ?
S2 O4 1.4331(14) . ?
S2 N1 1.6681(16) . ?
S2 C7 1.7644(18) . ?
N1 C13 1.482(2) . ?
C1 C2 1.390(2) . ?
C1 C6 1.392(2) . ?
C2 C3 1.388(3) . ?
C2 H2 0.91(3) . ?
C6 C5 1.392(3) . ?
C6 H6 0.96(2) . ?
C5 C4 1.390(3) . ?
C5 H5 0.96(3) . ?
C7 C12 1.392(3) . ?
C7 C8 1.388(3) . ?
C3 C4 1.393(3) . ?
C3 H3 0.97(3) . ?
C12 C11 1.384(3) . ?
C12 H12 1.01(2) . ?
C4 H4 0.96(3) . ?
C9 C10 1.389(3) . ?
C9 C8 1.388(3) . ?
C9 H9 0.99(3) . ?
C11 C10 1.389(3) . ?
C11 H11 0.94(3) . ?
C10 H10 0.97(3) . ?
C8 H8 0.93(3) . ?
C13 H13A 1.04(3) . ?
C13 H13B 0.99(3) . ?
C13 H13C 1.05(4) . ?

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
O2 S1 O1 119.60(8) . . ?
O2 S1 N1 108.94(8) . . ?
O2 S1 C1 109.33(8) . . ?
O1 S1 N1 104.49(8) . . ?
O1 S1 C1 108.57(8) . . ?
N1 S1 C1 104.88(8) . . ?
O3 S2 O4 120.28(9) . . ?
O3 S2 N1 107.41(8) . . ?
O3 S2 C7 110.25(9) . . ?
O4 S2 N1 105.22(9) . . ?
O4 S2 C7 107.99(8) . . ?
N1 S2 C7 104.47(8) . . ?
S2 N1 S1 122.91(9) . . ?
C13 N1 S1 118.23(13) . . ?
C13 N1 S2 115.85(13) . . ?
C2 C1 S1 118.50(13) . . ?
C2 C1 C6 122.27(16) . . ?
C6 C1 S1 119.21(13) . . ?
C1 C2 H2 121.1(16) . . ?
C3 C2 C1 118.75(17) . . ?
C3 C2 H2 120.2(16) . . ?
C1 C6 H6 118.3(14) . . ?
C5 C6 C1 118.21(17) . . ?
C5 C6 H6 123.5(14) . . ?
C6 C5 H5 118.7(16) . . ?
C4 C5 C6 120.26(17) . . ?
C4 C5 H5 121.1(16) . . ?
C12 C7 S2 119.16(14) . . ?
C8 C7 S2 119.04(14) . . ?
C8 C7 C12 121.78(17) . . ?
C2 C3 C4 119.88(17) . . ?
C2 C3 H3 119.0(15) . . ?
C4 C3 H3 121.0(15) . . ?
C7 C12 H12 120.0(14) . . ?
C11 C12 C7 119.04(18) . . ?
C11 C12 H12 121.0(14) . . ?
C5 C4 C3 120.63(17) . . ?
C5 C4 H4 119.4(15) . . ?
C3 C4 H4 119.9(15) . . ?
C10 C9 H9 121.0(17) . . ?
C8 C9 C10 120.66(19) . . ?
C8 C9 H9 118.3(17) . . ?
C12 C11 C10 120.01(18) . . ?
C12 C11 H11 119.3(16) . . ?
C10 C11 H11 120.7(16) . . ?
C9 C10 C11 120.16(18) . . ?
C9 C10 H10 118.3(16) . . ?
C11 C10 H10 121.5(16) . . ?
C7 C8 C9 118.33(18) . . ?
C7 C8 H8 120.3(16) . . ?
C9 C8 H8 121.4(16) . . ?
N1 C13 H13A 110.2(14) . . ?
N1 C13 H13B 102.3(16) . . ?
N1 C13 H13C 107.3(17) . . ?
H13A C13 H13B 111(2) . . ?
H13A C13 H13C 113(2) . . ?
H13B C13 H13C 113(2) . . ?

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 C1 C2 C3 -178.86(13) . . . . ?
S1 C1 C6 C5 179.21(13) . . . . ?
S2 C7 C12 C11 -178.07(13) . . . . ?
S2 C7 C8 C9 178.42(15) . . . . ?
O2 S1 N1 S2 31.23(12) . . . . ?
O2 S1 N1 C13 -128.30(14) . . . . ?
O2 S1 C1 C2 155.72(13) . . . . ?
O2 S1 C1 C6 -22.79(16) . . . . ?
O1 S1 N1 S2 160.14(10) . . . . ?
O1 S1 N1 C13 0.61(16) . . . . ?
O1 S1 C1 C2 23.65(16) . . . . ?
O1 S1 C1 C6 -154.86(14) . . . . ?
O3 S2 N1 S1 23.77(13) . . . . ?
O3 S2 N1 C13 -176.25(13) . . . . ?
O3 S2 C7 C12 -33.76(16) . . . . ?
O3 S2 C7 C8 147.39(15) . . . . ?
O4 S2 N1 S1 153.04(10) . . . . ?
O4 S2 N1 C13 -46.98(15) . . . . ?
O4 S2 C7 C12 -166.99(14) . . . . ?
O4 S2 C7 C8 14.16(18) . . . . ?
N1 S1 C1 C2 -87.60(14) . . . . ?
N1 S1 C1 C6 93.90(14) . . . . ?
N1 S2 C7 C12 81.36(15) . . . . ?
N1 S2 C7 C8 -97.49(15) . . . . ?
C1 S1 N1 S2 -85.72(11) . . . . ?
C1 S1 N1 C13 114.74(14) . . . . ?
C1 C2 C3 C4 -0.1(3) . . . . ?
C1 C6 C5 C4 -0.6(3) . . . . ?
C2 C1 C6 C5 0.8(3) . . . . ?
C2 C3 C4 C5 0.3(3) . . . . ?
C6 C1 C2 C3 -0.4(3) . . . . ?
C6 C5 C4 C3 0.1(3) . . . . ?
C7 S2 N1 S1 -93.33(11) . . . . ?
C7 S2 N1 C13 66.65(15) . . . . ?
C7 C12 C11 C10 0.0(3) . . . . ?
C12 C7 C8 C9 -0.4(3) . . . . ?
C12 C11 C10 C9 -1.0(3) . . . . ?
C10 C9 C8 C7 -0.6(3) . . . . ?
C8 C7 C12 C11 0.7(3) . . . . ?
C8 C9 C10 C11 1.3(3) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.290
_oxdiff_exptl_absorpt_empirical_full_min 0.680
####################################################################### 
# 
# 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_23h
_database_code_depnum_ccdc_archive 'CCDC 2051045'
loop_
_audit_author_name
_audit_author_address
'Felix Hennersdorf'
;TU Dresden
Germany
;
_audit_update_record             
;
2020-12-17 deposited with the CCDC.	2021-04-01 downloaded from the CCDC.
;
_audit_creation_date             2018-05-13
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H16 N2 O2 S'
_chemical_formula_sum            'C15 H16 N2 O2 S'
_chemical_formula_weight         288.36
_chemical_melting_point          ?
_chemical_oxdiff_formula         C15H17N2O2S
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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                   6.7867(3)
_cell_length_b                   8.5309(4)
_cell_length_c                   12.6966(6)
_cell_angle_alpha                76.999(4)
_cell_angle_beta                 77.348(4)
_cell_angle_gamma                83.351(4)
_cell_volume                     697.15(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3223
_cell_measurement_temperature    99.97(15)
_cell_measurement_theta_max      75.9880
_cell_measurement_theta_min      3.6580
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.089
_exptl_absorpt_correction_T_max  0.914
_exptl_absorpt_correction_T_min  0.759
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.374
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       irregular
_exptl_crystal_F_000             304
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -1 0 0.0360
0 1 0 0.0130
-4 -3 -4 0.0949
1 1 -2 0.0270
0 -2 -5 0.0380
-1 2 5 0.0336
2 -1 5 0.0887
1 -4 4 0.0580
1 -5 -3 0.0395

_exptl_crystal_size_max          0.223
_exptl_crystal_size_mid          0.089
_exptl_crystal_size_min          0.049
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0.0006 -0.9992 0.0022 0.1011 -0.0049 0.1557
-0.0006 0.9992 -0.0022 -0.1011 0.0049 -0.1557
-3.9997 -3.0048 -4.0023 -0.5873 0.0540 0.8447
1.0006 1.0000 -1.9990 -0.0423 -0.3564 -0.2485
0.0026 -2.0002 -4.9939 -0.0710 -0.5832 0.3142
-1.0032 1.9987 4.9914 -0.0970 0.7151 -0.2203
2.0004 -0.9947 5.0056 0.7102 0.3049 -0.0347
1.0018 -3.9942 4.0099 0.7908 0.3074 0.5269
1.0044 -4.9958 -2.9855 0.5095 -0.5004 0.6864

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0108
_diffrn_reflns_av_unetI/netI     0.0141
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            5616
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.464
_diffrn_reflns_theta_min         3.646
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.97(15)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.5700
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -125.00  44.00   0.50    4.00    --  -38.50   0.00 120.00  338
  2  ω     34.00  67.00   0.50    4.00    --   42.50-125.00  90.00   66
  3  ω     29.00 103.00   0.50    4.00    --   42.50-135.00-148.00  148
  4  ω     38.00  75.00   0.50    4.00    --   42.50-134.00  31.00   74
  5  ω     -1.00  60.00   0.50    4.00    --   42.50 -38.00-150.00  122
  6  ω     54.00  96.00   0.50   16.00    --  111.00 -30.00 -60.00   84
  7  ω     90.00 168.00   0.50   16.00    --  111.00  30.00 -60.00  156
  8  ω     52.00 138.00   0.50   16.00    --  111.00 -61.00 -90.00  172
  9  ω     62.00  99.00   0.50   16.00    --  111.00 -94.00-180.00   74
 10  ω     92.00 156.00   0.50   16.00    --  111.00  30.00   0.00  128
 11  ω     94.00 129.00   0.50   16.00    --  111.00 -45.00 120.00   70
 12  ω    117.00 177.00   0.50   16.00    --  111.00 125.00-180.00  120
 13  ω    141.00 178.00   0.50   16.00    --  111.00  77.00-120.00   74
 14  ω     30.00 109.00   0.50   16.00    --  111.00 -94.00 -90.00  158
 15  ω     87.00 175.00   0.50   16.00    --  111.00  30.00-120.00  176
 16  ω     47.00  89.00   0.50   16.00    --  111.00-125.00-180.00   84
 17  ω     78.00 119.00   0.50   16.00    --  111.00-125.00 -90.00   82
 18  ω     53.00  93.00   0.50   16.00    --  111.00 -45.00 120.00   80
 19  ω     90.00 118.00   0.50   16.00    --  111.00-125.00  60.00   56
 20  ω    126.00 169.00   0.50   16.00    --  111.00 125.00-150.00   86
 21  ω     83.00 115.00   0.50   16.00    --  111.00  61.00 -60.00   64
 22  ω    146.00 178.00   0.50   16.00    --  111.00  61.00 -60.00   64
 23  ω     90.00 121.00   0.50   16.00    --  111.00-125.00 150.00   62
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1679167000
_diffrn_orient_matrix_UB_12      -0.1009347000
_diffrn_orient_matrix_UB_13      0.0547252000
_diffrn_orient_matrix_UB_21      -0.1320652000
_diffrn_orient_matrix_UB_22      0.0050640000
_diffrn_orient_matrix_UB_23      0.1146927000
_diffrn_orient_matrix_UB_31      -0.0935576000
_diffrn_orient_matrix_UB_32      -0.1559002000
_diffrn_orient_matrix_UB_33      -0.0005145000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2813
_reflns_number_total             2876
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_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         0.294
_refine_diff_density_min         -0.442
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         2876
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0291
_refine_ls_R_factor_gt           0.0286
_refine_ls_restrained_S_all      1.077
_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)+(0.0418P)²+0.2654P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0778
_refine_ls_wR_factor_ref         0.0783
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C5(H5), C6(H6), C8(H8), C9(H9), C11(H11), C12(H12), C13(H13),
 C14(H14), C15(H15)
2.b Idealised Me refined as rotating group:
 C2(H2A,H2B,H2C), C3(H3A,H3B,H3C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.30583(4) 0.70644(3) 0.84407(2) 0.01499(10) Uani 1 1 d . . . . .
O1 O 0.16536(13) 0.84093(10) 0.81445(7) 0.02073(19) Uani 1 1 d . . . . .
O2 O 0.37822(13) 0.69420(10) 0.94511(7) 0.01909(18) Uani 1 1 d . . . . .
N1 N 0.20343(15) 0.54483(11) 0.84259(8) 0.0168(2) Uani 1 1 d . . . . .
N2 N 0.19032(14) 0.27141(11) 0.91153(8) 0.0160(2) Uani 1 1 d . . . . .
C1 C 0.25739(16) 0.41141(13) 0.90861(9) 0.0150(2) Uani 1 1 d . . . . .
H1 H 0.3453 0.4164 0.9544 0.018 Uiso 1 1 calc R . . . .
C2 C 0.04969(19) 0.25492(15) 0.84307(10) 0.0216(2) Uani 1 1 d . . . . .
H2A H -0.0861 0.2568 0.8853 0.032 Uiso 1 1 calc GR . . . .
H2B H 0.0823 0.1546 0.8188 0.032 Uiso 1 1 calc GR . . . .
H2C H 0.0605 0.3426 0.7801 0.032 Uiso 1 1 calc GR . . . .
C3 C 0.24568(18) 0.12614(14) 0.98860(10) 0.0197(2) Uani 1 1 d . . . . .
H3A H 0.3484 0.1487 1.0233 0.030 Uiso 1 1 calc GR . . . .
H3B H 0.2964 0.0413 0.9492 0.030 Uiso 1 1 calc GR . . . .
H3C H 0.1286 0.0931 1.0438 0.030 Uiso 1 1 calc GR . . . .
C4 C 0.51969(17) 0.71953(13) 0.73490(9) 0.0152(2) Uani 1 1 d . . . . .
C5 C 0.49578(17) 0.78858(13) 0.62763(10) 0.0173(2) Uani 1 1 d . . . . .
H5 H 0.3681 0.8267 0.6135 0.021 Uiso 1 1 calc R . . . .
C6 C 0.66383(18) 0.80014(13) 0.54195(10) 0.0174(2) Uani 1 1 d . . . . .
H6 H 0.6479 0.8460 0.4703 0.021 Uiso 1 1 calc R . . . .
C7 C 0.85695(17) 0.74357(13) 0.56213(9) 0.0157(2) Uani 1 1 d . . . . .
C8 C 0.87712(17) 0.67356(13) 0.67044(10) 0.0171(2) Uani 1 1 d . . . . .
H8 H 1.0045 0.6351 0.6848 0.020 Uiso 1 1 calc R . . . .
C9 C 0.71017(18) 0.66060(13) 0.75659(9) 0.0171(2) Uani 1 1 d . . . . .
H9 H 0.7252 0.6131 0.8281 0.020 Uiso 1 1 calc R . . . .
C10 C 1.03816(17) 0.75821(14) 0.47119(9) 0.0164(2) Uani 1 1 d . . . . .
C11 C 1.05406(18) 0.89290(14) 0.38396(10) 0.0184(2) Uani 1 1 d . . . . .
H11 H 0.9490 0.9731 0.3822 0.022 Uiso 1 1 calc R . . . .
C12 C 1.2252(2) 0.90788(15) 0.30008(10) 0.0220(3) Uani 1 1 d . . . . .
H12 H 1.2349 0.9985 0.2430 0.026 Uiso 1 1 calc R . . . .
C13 C 1.38156(19) 0.78795(16) 0.30134(10) 0.0234(3) Uani 1 1 d . . . . .
H13 H 1.4961 0.7982 0.2452 0.028 Uiso 1 1 calc R . . . .
C14 C 1.36732(19) 0.65225(15) 0.38652(11) 0.0227(3) Uani 1 1 d . . . . .
H14 H 1.4714 0.5711 0.3868 0.027 Uiso 1 1 calc R . . . .
C15 C 1.19723(18) 0.63818(14) 0.47121(10) 0.0192(2) Uani 1 1 d . . . . .
H15 H 1.1891 0.5480 0.5285 0.023 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 1.4409(8) . ?
S1 O2 1.4499(8) . ?
S1 N1 1.6197(10) . ?
S1 C4 1.7683(12) . ?
N1 C1 1.3194(15) . ?
N2 C1 1.3167(15) . ?
N2 C2 1.4614(15) . ?
N2 C3 1.4636(14) . ?
C1 H1 0.9300 . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?
C4 C5 1.3935(16) . ?
C4 C9 1.3939(16) . ?
C5 H5 0.9300 . ?
C5 C6 1.3886(17) . ?
C6 H6 0.9300 . ?
C6 C7 1.4005(16) . ?
C7 C8 1.4002(16) . ?
C7 C10 1.4865(16) . ?
C8 H8 0.9300 . ?
C8 C9 1.3872(17) . ?
C9 H9 0.9300 . ?
C10 C11 1.4008(16) . ?
C10 C15 1.3993(16) . ?
C11 H11 0.9300 . ?
C11 C12 1.3897(17) . ?
C12 H12 0.9300 . ?
C12 C13 1.3861(18) . ?
C13 H13 0.9300 . ?
C13 C14 1.3914(18) . ?
C14 H14 0.9300 . ?
C14 C15 1.3905(18) . ?
C15 H15 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 O2 117.43(5) . . ?
O1 S1 N1 106.93(5) . . ?
O1 S1 C4 107.15(5) . . ?
O2 S1 N1 112.17(5) . . ?
O2 S1 C4 107.35(5) . . ?
N1 S1 C4 105.03(5) . . ?
C1 N1 S1 116.33(8) . . ?
C1 N2 C2 122.04(10) . . ?
C1 N2 C3 120.95(10) . . ?
C2 N2 C3 116.93(9) . . ?
N1 C1 H1 119.1 . . ?
N2 C1 N1 121.89(10) . . ?
N2 C1 H1 119.1 . . ?
N2 C2 H2A 109.5 . . ?
N2 C2 H2B 109.5 . . ?
N2 C2 H2C 109.5 . . ?
H2A C2 H2B 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
N2 C3 H3A 109.5 . . ?
N2 C3 H3B 109.5 . . ?
N2 C3 H3C 109.5 . . ?
H3A C3 H3B 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C5 C4 S1 119.50(9) . . ?
C5 C4 C9 120.58(11) . . ?
C9 C4 S1 119.92(9) . . ?
C4 C5 H5 120.2 . . ?
C6 C5 C4 119.56(10) . . ?
C6 C5 H5 120.2 . . ?
C5 C6 H6 119.6 . . ?
C5 C6 C7 120.78(10) . . ?
C7 C6 H6 119.6 . . ?
C6 C7 C10 121.12(10) . . ?
C8 C7 C6 118.66(11) . . ?
C8 C7 C10 120.22(10) . . ?
C7 C8 H8 119.5 . . ?
C9 C8 C7 121.06(10) . . ?
C9 C8 H8 119.5 . . ?
C4 C9 H9 120.3 . . ?
C8 C9 C4 119.35(10) . . ?
C8 C9 H9 120.3 . . ?
C11 C10 C7 120.76(10) . . ?
C15 C10 C7 120.71(10) . . ?
C15 C10 C11 118.53(11) . . ?
C10 C11 H11 119.7 . . ?
C12 C11 C10 120.70(11) . . ?
C12 C11 H11 119.7 . . ?
C11 C12 H12 120.0 . . ?
C13 C12 C11 120.06(11) . . ?
C13 C12 H12 120.0 . . ?
C12 C13 H13 120.0 . . ?
C12 C13 C14 120.07(11) . . ?
C14 C13 H13 120.0 . . ?
C13 C14 H14 120.1 . . ?
C15 C14 C13 119.89(11) . . ?
C15 C14 H14 120.1 . . ?
C10 C15 H15 119.6 . . ?
C14 C15 C10 120.75(11) . . ?
C14 C15 H15 119.6 . . ?

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 N1 C1 N2 -177.37(8) . . . . ?
S1 C4 C5 C6 179.47(8) . . . . ?
S1 C4 C9 C8 -179.14(8) . . . . ?
O1 S1 N1 C1 -152.27(9) . . . . ?
O1 S1 C4 C5 -30.15(10) . . . . ?
O1 S1 C4 C9 150.00(9) . . . . ?
O2 S1 N1 C1 -22.19(10) . . . . ?
O2 S1 C4 C5 -157.12(9) . . . . ?
O2 S1 C4 C9 23.03(10) . . . . ?
N1 S1 C4 C5 83.32(10) . . . . ?
N1 S1 C4 C9 -96.53(10) . . . . ?
C2 N2 C1 N1 -0.87(17) . . . . ?
C3 N2 C1 N1 -177.50(10) . . . . ?
C4 S1 N1 C1 94.10(9) . . . . ?
C4 C5 C6 C7 -0.15(17) . . . . ?
C5 C4 C9 C8 1.01(17) . . . . ?
C5 C6 C7 C8 0.61(16) . . . . ?
C5 C6 C7 C10 -178.86(10) . . . . ?
C6 C7 C8 C9 -0.27(16) . . . . ?
C6 C7 C10 C11 35.66(15) . . . . ?
C6 C7 C10 C15 -144.74(11) . . . . ?
C7 C8 C9 C4 -0.54(17) . . . . ?
C7 C10 C11 C12 178.78(10) . . . . ?
C7 C10 C15 C14 -179.61(10) . . . . ?
C8 C7 C10 C11 -143.80(11) . . . . ?
C8 C7 C10 C15 35.80(15) . . . . ?
C9 C4 C5 C6 -0.68(17) . . . . ?
C10 C7 C8 C9 179.21(10) . . . . ?
C10 C11 C12 C13 0.79(18) . . . . ?
C11 C10 C15 C14 0.00(17) . . . . ?
C11 C12 C13 C14 0.08(18) . . . . ?
C12 C13 C14 C15 -0.90(18) . . . . ?
C13 C14 C15 C10 0.86(18) . . . . ?
C15 C10 C11 C12 -0.82(17) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.359
_oxdiff_exptl_absorpt_empirical_full_min 0.813
####################################################################### 
# 
# 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_21a
_database_code_depnum_ccdc_archive 'CCDC 2051043'
loop_
_audit_author_name
_audit_author_address
'Felix Hennersdorf'
;TU Dresden
Germany
;
_audit_update_record             
;
2020-12-17 deposited with the CCDC.	2021-04-01 downloaded from the CCDC.
;
_audit_creation_date             2019-08-28
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C8 H10 N2 O2 S'
_chemical_formula_sum            'C8 H10 N2 O2 S'
_chemical_formula_weight         198.24
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C32 H44 N8 O8 S4 '
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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                   8.40980(10)
_cell_length_b                   7.39730(10)
_cell_length_c                   15.1632(2)
_cell_angle_alpha                90
_cell_angle_beta                 95.8890(10)
_cell_angle_gamma                90
_cell_volume                     938.32(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5829
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      75.9830
_cell_measurement_theta_min      5.7750
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.835
_exptl_absorpt_correction_T_max  0.879
_exptl_absorpt_correction_T_min  0.660
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.403
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             416
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
5 0 1 0.0431
-5 -1 -1 0.0326
0 -1 0 0.1363
-1 5 0 0.1824
0 0 1 0.0578
0 0 -1 0.0184
-1 -1 -5 0.0365
-1 -1 10 0.0738
1 1 0 0.1661
2 0 -5 0.0010
1 -1 -5 0.0455
0 2 5 0.1463
-5 2 3 0.0648
-4 3 -4 0.0927
1 -2 5 0.1063
-3 -1 5 0.0605

_exptl_crystal_size_max          0.328
_exptl_crystal_size_mid          0.108
_exptl_crystal_size_min          0.075
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
5.0000 -0.0000 1.0000 0.5389 0.4196 -0.6418
-5.0000 -1.0000 -1.0000 -0.4279 -0.3302 0.7935
0.0000 -1.0000 0.0000 0.1110 0.0894 0.1517
-1.0000 5.0000 -0.0000 -0.6728 -0.5133 -0.6333
0.0000 -0.0000 1.0000 -0.0497 0.0879 -0.0156
-0.0000 0.0000 -1.0000 0.0497 -0.0879 0.0156
-1.0000 -1.0000 -5.0000 0.2416 -0.4164 0.3551
-1.0000 -1.0000 10.0000 -0.5033 0.9020 0.1206
1.0000 1.0000 -0.0000 0.0067 -0.0230 -0.2769
2.0000 -0.0000 -5.0000 0.4837 -0.3068 -0.1723
1.0000 -1.0000 -5.0000 0.4770 -0.2837 0.1046
-0.0000 2.0000 5.0000 -0.4703 0.2607 -0.3816
-5.0000 2.0000 3.0000 -0.9596 -0.2468 0.2759
-4.0000 3.0000 -4.0000 -0.6053 -0.8851 0.1084
1.0000 -2.0000 5.0000 0.0914 0.6846 0.1000
-3.0000 -1.0000 5.0000 -0.4904 0.3298 0.4492

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0213
_diffrn_reflns_av_unetI/netI     0.0177
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            8201
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.608
_diffrn_reflns_theta_min         5.779
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2850
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -59.00  33.00   1.00    1.50    --  -38.50  38.00 -30.00   92
  2  ω    -64.00  32.00   1.00    1.50    --  -38.50  57.00-180.00   96
  3  ω      7.00  37.00   1.00    1.50    --   42.50 -99.00-120.00   30
  4  ω     56.00  98.00   1.00    1.50    --   42.50-125.00 -30.00   42
  5  ω     41.00  68.00   1.00    6.00    --  111.00 -45.00   0.00   27
  6  ω     51.00 137.00   1.00    6.00    --  111.00 -61.00  30.00   86
  7  ω     77.00 104.00   1.00    6.00    --  111.00 -94.00 120.00   27
  8  ω     66.00 135.00   1.00    6.00    --  111.00 -45.00 150.00   69
  9  ω     87.00 156.00   1.00    6.00    --  111.00  30.00  60.00   69
 10  ω    100.00 149.00   1.00    6.00    --  111.00  30.00 -30.00   49
 11  ω     91.00 171.00   1.00    6.00    --  111.00  45.00   0.00   80
 12  ω    128.00 178.00   1.00    6.00    --  111.00 125.00-120.00   50
 13  ω    119.00 146.00   1.00    6.00    --  111.00 125.00-150.00   27
 14  ω     87.00 137.00   1.00    6.00    --  111.00  30.00-180.00   50
 15  ω     91.00 178.00   1.00    6.00    --  111.00  30.00 -90.00   87
 16  ω    111.00 138.00   1.00    6.00    --  111.00 -77.00-180.00   27
 17  ω     67.00 104.00   1.00    6.00    --  111.00 -94.00-120.00   37
 18  ω     57.00  90.00   1.00    6.00    --  111.00 -77.00-180.00   33
 19  ω     60.00  86.00   1.00    6.00    --  111.00-125.00-150.00   26
 20  ω     39.00 114.00   1.00    6.00    --  111.00-125.00-120.00   75
 21  ω     74.00 121.00   1.00    6.00    --  111.00-125.00   0.00   47
 22  ω     65.00 109.00   1.00    6.00    --  111.00 -94.00  30.00   44
 23  ω     54.00 109.00   1.00    6.00    --  111.00 -94.00   0.00   55
 24  ω     54.00 132.00   1.00    6.00    --  111.00 -45.00-120.00   78
 25  ω     40.00  67.00   1.00    6.00    --  111.00-125.00 120.00   27
 26  ω   -109.00 -18.00   1.00    1.50    --  -38.50 -57.00  30.00   91
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1177141000
_diffrn_orient_matrix_UB_12      -0.1110161000
_diffrn_orient_matrix_UB_13      -0.0496630000
_diffrn_orient_matrix_UB_21      0.0663390000
_diffrn_orient_matrix_UB_22      -0.0893861000
_diffrn_orient_matrix_UB_23      0.0878948000
_diffrn_orient_matrix_UB_31      -0.1252344000
_diffrn_orient_matrix_UB_32      -0.1516976000
_diffrn_orient_matrix_UB_33      -0.0156315000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1910
_reflns_number_total             1957
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_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         0.394
_refine_diff_density_min         -0.413
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     123
_refine_ls_number_reflns         1957
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0314
_refine_ls_R_factor_gt           0.0308
_refine_ls_restrained_S_all      1.056
_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)+(0.0351P)²+0.7220P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0792
_refine_ls_wR_factor_ref         0.0797
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C7(H7)
2.b Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.37507(16) 0.57688(18) 0.34046(9) 0.0141(3) Uani 1 1 d . . . . .
C2 C 0.32609(16) 0.47050(18) 0.40819(9) 0.0151(3) Uani 1 1 d . . . . .
H2 H 0.4006 0.4083 0.4464 0.018 Uiso 1 1 calc R . . . .
C3 C 0.16394(17) 0.4586(2) 0.41786(10) 0.0186(3) Uani 1 1 d . . . . .
H3 H 0.1295 0.3890 0.4633 0.022 Uiso 1 1 calc R . . . .
C4 C 0.05322(17) 0.5499(2) 0.36016(11) 0.0210(3) Uani 1 1 d . . . . .
H4 H -0.0552 0.5407 0.3668 0.025 Uiso 1 1 calc R . . . .
C5 C 0.10370(18) 0.6551(2) 0.29236(11) 0.0248(3) Uani 1 1 d . . . . .
H5 H 0.0290 0.7156 0.2536 0.030 Uiso 1 1 calc R . . . .
C6 C 0.26557(18) 0.6700(2) 0.28236(10) 0.0215(3) Uani 1 1 d . . . . .
H6 H 0.3001 0.7412 0.2375 0.026 Uiso 1 1 calc R . . . .
C7 C 0.67999(19) 0.9096(2) 0.36604(11) 0.0243(3) Uani 1 1 d . . . . .
H7 H 0.6775 0.9201 0.3048 0.029 Uiso 1 1 calc R . . . .
C8 C 0.7348(2) 1.0503(2) 0.51131(12) 0.0325(4) Uani 1 1 d . . . . .
H8A H 0.6449 0.9866 0.5303 0.049 Uiso 1 1 calc GR . . . .
H8B H 0.7342 1.1728 0.5322 0.049 Uiso 1 1 calc GR . . . .
H8C H 0.8319 0.9920 0.5350 0.049 Uiso 1 1 calc GR . . . .
N1 N 0.63864(13) 0.75642(16) 0.39980(8) 0.0158(2) Uani 1 1 d . . . . .
N2 N 0.72499(19) 1.04945(19) 0.41585(11) 0.0314(3) Uani 1 1 d . . . . .
H2A H 0.748(3) 1.142(3) 0.3927(16) 0.044(6) Uiso 1 1 d . . . . .
O1 O 0.59971(13) 0.64831(17) 0.23949(7) 0.0252(3) Uani 1 1 d . . . . .
O2 O 0.65712(12) 0.43291(14) 0.36236(8) 0.0217(2) Uani 1 1 d . . . . .
S1 S 0.58152(4) 0.59837(4) 0.32985(2) 0.01504(12) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.3894(19) . ?
C1 C6 1.390(2) . ?
C1 S1 1.7672(14) . ?
C2 H2 0.9300 . ?
C2 C3 1.3891(19) . ?
C3 H3 0.9300 . ?
C3 C4 1.386(2) . ?
C4 H4 0.9300 . ?
C4 C5 1.390(2) . ?
C5 H5 0.9300 . ?
C5 C6 1.389(2) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C7 N1 1.3052(19) . ?
C7 N2 1.313(2) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C8 N2 1.441(2) . ?
N1 S1 1.6180(12) . ?
N2 H2A 0.80(3) . ?
O1 S1 1.4423(11) . ?
O2 S1 1.4425(11) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 121.45(13) . . ?
C2 C1 S1 119.13(10) . . ?
C6 C1 S1 119.40(11) . . ?
C1 C2 H2 120.6 . . ?
C3 C2 C1 118.85(13) . . ?
C3 C2 H2 120.6 . . ?
C2 C3 H3 119.8 . . ?
C4 C3 C2 120.38(13) . . ?
C4 C3 H3 119.8 . . ?
C3 C4 H4 119.9 . . ?
C3 C4 C5 120.21(14) . . ?
C5 C4 H4 119.9 . . ?
C4 C5 H5 119.9 . . ?
C6 C5 C4 120.14(14) . . ?
C6 C5 H5 119.9 . . ?
C1 C6 H6 120.5 . . ?
C5 C6 C1 118.97(14) . . ?
C5 C6 H6 120.5 . . ?
N1 C7 H7 119.0 . . ?
N1 C7 N2 122.07(15) . . ?
N2 C7 H7 119.0 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N2 C8 H8A 109.5 . . ?
N2 C8 H8B 109.5 . . ?
N2 C8 H8C 109.5 . . ?
C7 N1 S1 116.32(11) . . ?
C7 N2 C8 124.35(14) . . ?
C7 N2 H2A 119.1(17) . . ?
C8 N2 H2A 116.5(17) . . ?
N1 S1 C1 103.52(6) . . ?
O1 S1 C1 108.09(6) . . ?
O1 S1 N1 112.61(7) . . ?
O1 S1 O2 117.13(7) . . ?
O2 S1 C1 107.17(6) . . ?
O2 S1 N1 107.35(6) . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.752
_oxdiff_exptl_absorpt_empirical_full_min 0.577
####################################################################### 
# 
# 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_14
_database_code_depnum_ccdc_archive 'CCDC 2051047'
loop_
_audit_author_name
_audit_author_address
'Felix Hennersdorf'
;TU Dresden
Germany
;
_audit_update_record             
;
2020-12-17 deposited with the CCDC.	2021-04-01 downloaded from the CCDC.
;
_audit_creation_date             2017-08-30
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H24 N2 O2 S'
_chemical_formula_sum            'C15 H24 N2 O2 S'
_chemical_formula_weight         296.42
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C60 H96 N8 O8 S4 '
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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                   9.91994(16)
_cell_length_b                   7.80758(13)
_cell_length_c                   20.4247(4)
_cell_angle_alpha                90
_cell_angle_beta                 100.3314(17)
_cell_angle_gamma                90
_cell_volume                     1556.26(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5455
_cell_measurement_temperature    100.0(3)
_cell_measurement_theta_max      76.2060
_cell_measurement_theta_min      4.3990
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.873
_exptl_absorpt_correction_T_max  0.955
_exptl_absorpt_correction_T_min  0.685
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.265
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             640
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-5 0 -5 0.0499
1 5 -4 0.1484
0 0 13 0.0154
6 0 -8 0.0035
-6 0 8 0.0235
-3 3 -6 0.1160
-2 -5 2 0.1430
5 0 5 0.0010
0 0 -13 0.0308

_exptl_crystal_size_max          0.315
_exptl_crystal_size_mid          0.055
_exptl_crystal_size_min          0.027
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-4.9996 0.0028 -5.0018 0.1152 0.3806 -0.8487
0.9874 4.9984 -3.9864 0.2115 0.9264 0.4131
-0.0009 -0.0100 12.9975 -0.8828 -0.2661 0.3761
6.0005 0.0074 -7.9951 0.8125 -0.1702 0.6134
-6.0005 -0.0074 7.9951 -0.8125 0.1702 -0.6134
-3.0073 3.0011 -5.9931 0.2099 0.8299 -0.3632
-1.9872 -4.9971 1.9862 -0.1206 -0.8299 -0.6118
4.9996 -0.0028 5.0018 -0.1152 -0.3806 0.8487
0.0009 0.0100 -12.9975 0.8828 0.2661 -0.3761

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0299
_diffrn_reflns_av_unetI/netI     0.0257
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            10157
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.380
_diffrn_reflns_theta_min         4.401
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.0(3)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2850
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -111.00 -16.00   0.50    9.00    --  -38.50 -38.00   0.00  190
  2  ω   -111.00 -16.00   0.50    9.00    --  -38.50 -38.00-150.00  190
  3  ω    -61.00  34.00   0.50    9.00    --  -38.50  38.00  90.00  190
  4  ω     43.00  79.00   0.50   36.00    --  111.00 -61.00-150.00   72
  5  ω      1.00  82.00   0.50    9.00    --   42.00 -99.00-120.00  162
  6  ω     87.00 178.00   0.50   36.00    --  111.00  30.00  60.00  182
  7  ω     83.00 178.00   0.50   36.00    --  111.00  61.00   0.00  190
  8  ω     66.00 178.00   0.50   36.00    --  111.00  15.00 -60.00  224
  9  ω     36.00 135.00   0.50   36.00    --  111.00 -30.00-150.00  198
 10  ω     30.00 109.00   0.50   36.00    --  111.00 -94.00-150.00  158
 11  ω     43.00 139.00   0.50   36.00    --  111.00 -61.00-150.00  192
 12  ω    110.00 139.00   0.50   36.00    --  111.00 -61.00-150.00   58
 13  ω     93.00 130.00   0.50   36.00    --  111.00 -61.00-180.00   74
 14  ω     69.00 114.00   0.50   36.00    --  111.00 -30.00 -30.00   90
 15  ω     51.00 108.00   0.50   36.00    --  111.00 -94.00 -90.00  114
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0449054000
_diffrn_orient_matrix_UB_12      -0.0207342000
_diffrn_orient_matrix_UB_13      -0.0679374000
_diffrn_orient_matrix_UB_21      -0.0556803000
_diffrn_orient_matrix_UB_22      0.1801282000
_diffrn_orient_matrix_UB_23      -0.0203361000
_diffrn_orient_matrix_UB_31      0.1407772000
_diffrn_orient_matrix_UB_32      0.0779685000
_diffrn_orient_matrix_UB_33      0.0290065000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2978
_reflns_number_total             3210
_reflns_odcompleteness_completeness 98.87
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_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 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_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         0.589
_refine_diff_density_min         -0.805
_refine_diff_density_rms         0.076
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         3210
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0463
_refine_ls_R_factor_gt           0.0439
_refine_ls_restrained_S_all      1.057
_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)+(0.0830P)²+0.4257P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1178
_refine_ls_wR_factor_ref         0.1211
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C6(H6A,H6B), C7(H7A,H7B), C8(H8A,H8B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C11(H11), C12(H12), C13(H13), C14(H14), C15(H15)
2.c Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C), C9(H9A,H9B,H9C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.36098(3) 0.30996(4) 0.42392(2) 0.01593(14) Uani 1 1 d . . . . .
O1 O 0.50464(10) 0.28313(14) 0.45114(5) 0.0207(2) Uani 1 1 d . . . . .
O2 O 0.32955(11) 0.43146(13) 0.37025(5) 0.0225(2) Uani 1 1 d . . . . .
N1 N 0.27224(12) 0.35834(16) 0.48069(6) 0.0180(3) Uani 1 1 d . . . . .
N2 N 0.28055(12) 0.39971(16) 0.59363(6) 0.0179(3) Uani 1 1 d . . . . .
C1 C 0.34009(14) 0.36757(17) 0.54197(7) 0.0169(3) Uani 1 1 d . . . . .
H1 H 0.4344 0.3507 0.5494 0.020 Uiso 1 1 calc R . . . .
C2 C 0.36407(15) 0.4029(2) 0.66083(7) 0.0206(3) Uani 1 1 d . . . . .
H2A H 0.3322 0.4950 0.6860 0.025 Uiso 1 1 calc R . . . .
H2B H 0.4585 0.4269 0.6574 0.025 Uiso 1 1 calc R . . . .
C3 C 0.35851(15) 0.2346(2) 0.69855(8) 0.0219(3) Uani 1 1 d . . . . .
H3A H 0.4049 0.2502 0.7442 0.026 Uiso 1 1 calc R . . . .
H3B H 0.2635 0.2072 0.6995 0.026 Uiso 1 1 calc R . . . .
C4 C 0.42387(15) 0.0842(2) 0.66832(8) 0.0222(3) Uani 1 1 d . . . . .
H4A H 0.5182 0.1124 0.6662 0.027 Uiso 1 1 calc R . . . .
H4B H 0.3756 0.0654 0.6232 0.027 Uiso 1 1 calc R . . . .
C5 C 0.42068(18) -0.0803(2) 0.70841(9) 0.0295(4) Uani 1 1 d . . . . .
H5A H 0.4611 -0.1718 0.6872 0.044 Uiso 1 1 calc GR . . . .
H5B H 0.3275 -0.1087 0.7107 0.044 Uiso 1 1 calc GR . . . .
H5C H 0.4715 -0.0638 0.7526 0.044 Uiso 1 1 calc GR . . . .
C6 C 0.13132(14) 0.4232(2) 0.58645(8) 0.0210(3) Uani 1 1 d . . . . .
H6A H 0.0957 0.3401 0.6143 0.025 Uiso 1 1 calc R . . . .
H6B H 0.0893 0.4004 0.5406 0.025 Uiso 1 1 calc R . . . .
C7 C 0.09003(15) 0.6023(2) 0.60528(8) 0.0218(3) Uani 1 1 d . . . . .
H7A H -0.0092 0.6082 0.5987 0.026 Uiso 1 1 calc R . . . .
H7B H 0.1250 0.6207 0.6522 0.026 Uiso 1 1 calc R . . . .
C8 C 0.14164(15) 0.7461(2) 0.56569(8) 0.0233(3) Uani 1 1 d . . . . .
H8A H 0.2410 0.7476 0.5753 0.028 Uiso 1 1 calc R . . . .
H8B H 0.1132 0.7236 0.5185 0.028 Uiso 1 1 calc R . . . .
C9 C 0.08783(17) 0.9210(2) 0.58191(9) 0.0299(4) Uani 1 1 d . . . . .
H9A H 0.1239 1.0075 0.5564 0.045 Uiso 1 1 calc GR . . . .
H9B H 0.1161 0.9442 0.6285 0.045 Uiso 1 1 calc GR . . . .
H9C H -0.0104 0.9214 0.5710 0.045 Uiso 1 1 calc GR . . . .
C10 C 0.29102(13) 0.11136(18) 0.39348(7) 0.0163(3) Uani 1 1 d . . . . .
C11 C 0.31080(14) -0.03174(19) 0.43502(7) 0.0174(3) Uani 1 1 d . . . . .
H11 H 0.3559 -0.0215 0.4789 0.021 Uiso 1 1 calc R . . . .
C12 C 0.26225(15) -0.18948(18) 0.40998(8) 0.0198(3) Uani 1 1 d . . . . .
H12 H 0.2749 -0.2861 0.4370 0.024 Uiso 1 1 calc R . . . .
C13 C 0.19421(16) -0.20331(19) 0.34400(8) 0.0226(3) Uani 1 1 d . . . . .
H13 H 0.1622 -0.3094 0.3273 0.027 Uiso 1 1 calc R . . . .
C14 C 0.17406(15) -0.0599(2) 0.30332(8) 0.0231(3) Uani 1 1 d . . . . .
H14 H 0.1285 -0.0701 0.2595 0.028 Uiso 1 1 calc R . . . .
C15 C 0.22215(15) 0.09955(19) 0.32805(7) 0.0200(3) Uani 1 1 d . . . . .
H15 H 0.2084 0.1964 0.3012 0.024 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 1.4490(10) . ?
S1 O2 1.4408(11) . ?
S1 N1 1.6213(12) . ?
S1 C10 1.7657(14) . ?
N1 C1 1.3124(18) . ?
N2 C1 1.3225(19) . ?
N2 C2 1.4708(17) . ?
N2 C6 1.4727(18) . ?
C1 H1 0.9300 . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C3 1.529(2) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.525(2) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 C5 1.527(2) . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 C7 1.525(2) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C8 1.525(2) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C9 1.524(2) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 C11 1.3953(19) . ?
C10 C15 1.391(2) . ?
C11 H11 0.9300 . ?
C11 C12 1.386(2) . ?
C12 H12 0.9300 . ?
C12 C13 1.399(2) . ?
C13 H13 0.9300 . ?
C13 C14 1.387(2) . ?
C14 H14 0.9300 . ?
C14 C15 1.395(2) . ?
C15 H15 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 N1 112.46(6) . . ?
O1 S1 C10 107.79(6) . . ?
O2 S1 O1 116.80(7) . . ?
O2 S1 N1 108.63(6) . . ?
O2 S1 C10 107.01(7) . . ?
N1 S1 C10 103.11(7) . . ?
C1 N1 S1 116.32(10) . . ?
C1 N2 C2 119.37(12) . . ?
C1 N2 C6 121.94(12) . . ?
C2 N2 C6 118.61(12) . . ?
N1 C1 N2 123.04(13) . . ?
N1 C1 H1 118.5 . . ?
N2 C1 H1 118.5 . . ?
N2 C2 H2A 109.0 . . ?
N2 C2 H2B 109.0 . . ?
N2 C2 C3 113.00(12) . . ?
H2A C2 H2B 107.8 . . ?
C3 C2 H2A 109.0 . . ?
C3 C2 H2B 109.0 . . ?
C2 C3 H3A 108.8 . . ?
C2 C3 H3B 108.8 . . ?
H3A C3 H3B 107.7 . . ?
C4 C3 C2 113.66(13) . . ?
C4 C3 H3A 108.8 . . ?
C4 C3 H3B 108.8 . . ?
C3 C4 H4A 109.1 . . ?
C3 C4 H4B 109.1 . . ?
C3 C4 C5 112.31(13) . . ?
H4A C4 H4B 107.9 . . ?
C5 C4 H4A 109.1 . . ?
C5 C4 H4B 109.1 . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
N2 C6 H6A 108.9 . . ?
N2 C6 H6B 108.9 . . ?
N2 C6 C7 113.56(12) . . ?
H6A C6 H6B 107.7 . . ?
C7 C6 H6A 108.9 . . ?
C7 C6 H6B 108.9 . . ?
C6 C7 H7A 108.7 . . ?
C6 C7 H7B 108.7 . . ?
H7A C7 H7B 107.6 . . ?
C8 C7 C6 114.21(13) . . ?
C8 C7 H7A 108.7 . . ?
C8 C7 H7B 108.7 . . ?
C7 C8 H8A 109.1 . . ?
C7 C8 H8B 109.1 . . ?
H8A C8 H8B 107.9 . . ?
C9 C8 C7 112.35(13) . . ?
C9 C8 H8A 109.1 . . ?
C9 C8 H8B 109.1 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C11 C10 S1 119.05(11) . . ?
C15 C10 S1 119.40(11) . . ?
C15 C10 C11 121.50(13) . . ?
C10 C11 H11 120.5 . . ?
C12 C11 C10 119.04(13) . . ?
C12 C11 H11 120.5 . . ?
C11 C12 H12 120.0 . . ?
C11 C12 C13 119.97(14) . . ?
C13 C12 H12 120.0 . . ?
C12 C13 H13 119.8 . . ?
C14 C13 C12 120.50(13) . . ?
C14 C13 H13 119.8 . . ?
C13 C14 H14 120.0 . . ?
C13 C14 C15 120.01(13) . . ?
C15 C14 H14 120.0 . . ?
C10 C15 C14 118.97(13) . . ?
C10 C15 H15 120.5 . . ?
C14 C15 H15 120.5 . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.010
_oxdiff_exptl_absorpt_empirical_full_min 0.470
####################################################################### 
# 
# 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_24a
_database_code_depnum_ccdc_archive 'CCDC 2051053'
loop_
_audit_author_name
_audit_author_address
'Felix Hennersdorf'
;TU Dresden
Germany
;
_audit_update_record             
;
2020-12-17 deposited with the CCDC.	2021-04-01 downloaded from the CCDC.
;
_audit_creation_date             2017-08-30
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H13 N O5 S2'
_chemical_formula_sum            'C13 H13 N O5 S2'
_chemical_formula_weight         327.36
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C26 H24 N2 O10 S4 '
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   8.12358(8)
_cell_length_b                   7.45938(6)
_cell_length_c                   11.44023(10)
_cell_angle_alpha                90
_cell_angle_beta                 97.7219(8)
_cell_angle_gamma                90
_cell_volume                     686.956(11)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5443
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      76.4230
_cell_measurement_theta_min      3.8970
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    3.730
_exptl_absorpt_correction_T_max  0.766
_exptl_absorpt_correction_T_min  0.709
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.583
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             340
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 5 -2 0.0486
-1 -5 2 0.0484
3 -4 0 0.0461
-3 4 1 0.0652
0 0 -7 0.0461
0 0 7 0.0580
2 -3 -5 0.0596
-2 3 -5 0.0655
5 0 -1 0.0220
-5 -2 0 0.0667
-2 -4 -1 0.0451
4 0 4 0.0364
-5 -1 3 0.0743
-5 2 0 0.0701
-2 -1 7 0.0729

_exptl_crystal_size_max          0.126
_exptl_crystal_size_mid          0.105
_exptl_crystal_size_min          0.097
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0.9990 4.9986 -1.9980 0.4175 -0.5624 -0.8194
-0.9990 -4.9986 1.9980 -0.4175 0.5624 0.8194
2.9997 -3.9993 -0.0032 -0.2456 -0.2114 0.9523
-2.9994 3.9993 1.0028 0.3538 0.2742 -0.8995
-0.0016 0.0002 -6.9970 -0.7580 -0.4395 -0.3697
0.0016 -0.0002 6.9970 0.7580 0.4395 0.3697
1.9987 -2.9993 -5.0001 -0.7428 -0.4356 0.4250
-2.0010 2.9996 -4.9956 -0.3400 -0.1923 -0.9532
4.9987 -0.0006 -1.0025 0.2360 -0.8008 0.4489
-4.9988 -1.9988 0.0022 -0.5704 0.8537 -0.1760
-1.9995 -3.9986 -0.9998 -0.6981 0.4638 0.3978
4.0001 -0.0007 3.9960 0.7086 -0.3392 0.6126
-4.9982 -0.9992 3.0013 -0.1325 0.9842 -0.1804
-4.9991 2.0001 0.0036 -0.1182 0.6223 -0.8273
-1.9979 -0.9997 6.9978 0.5072 0.7926 0.3319

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0148
_diffrn_reflns_av_unetI/netI     0.0197
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6494
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.591
_diffrn_reflns_theta_min         3.899
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2850
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -53.00  34.00   0.50    0.50    --  -38.50  38.00  60.00  174
  2  ω     17.00 106.00   0.50    0.50    --   42.75  57.00 150.00  178
  3  ω     81.00 108.00   0.50    2.00    --  111.00  77.00 150.00   54
  4  ω     83.00 109.00   0.50    2.00    --  111.00  61.00 150.00   52
  5  ω     89.00 163.00   0.50    2.00    --  111.00  45.00 120.00  148
  6  ω    152.00 178.00   0.50    2.00    --  111.00  61.00 150.00   52
  7  ω    135.00 172.00   0.50    2.00    --  111.00  45.00  90.00   74
  8  ω     96.00 127.00   0.50    2.00    --  111.00 125.00   0.00   62
  9  ω     84.00 152.00   0.50    2.00    --  111.00  61.00   0.00  136
 10  ω     91.00 131.00   0.50    2.00    --  111.00  45.00 -90.00   80
 11  ω     85.00 152.00   0.50    2.00    --  111.00  61.00 -60.00  134
 12  ω     96.00 169.00   0.50    2.00    --  111.00  77.00-180.00  146
 13  ω     83.00 128.00   0.50    2.00    --  111.00  61.00-180.00   90
 14  ω     88.00 115.00   0.50    2.00    --  111.00  45.00-180.00   54
 15  ω     34.00  98.00   0.50    2.00    --  111.00 -94.00 -30.00  128
 16  ω     84.00 109.00   0.50    2.00    --  111.00 -94.00   0.00   50
 17  ω     82.00 134.00   0.50    2.00    --  111.00 -30.00  90.00  104
 18  ω     87.00 168.00   0.50    2.00    --  111.00  45.00 150.00  162
 19  ω     88.00 126.00   0.50    2.00    --  111.00  45.00  90.00   76
 20  ω     86.00 113.00   0.50    2.00    --  111.00  61.00  90.00   54
 21  ω     83.00 110.00   0.50    2.00    --  111.00  61.00 120.00   54
 22  ω     80.00 107.00   0.50    2.00    --  111.00  77.00 120.00   54
 23  ω     51.00  76.00   0.50    2.00    --  111.00 -30.00  90.00   50
 24  ω     30.00  64.00   0.50    2.00    --  111.00 -94.00   0.00   68
 25  ω     30.00  76.00   0.50    2.00    --  111.00 -94.00 -90.00   92
 26  ω     33.00 107.00   0.50    2.00    --  111.00 -94.00-180.00  148
 27  ω    -59.00  -9.00   0.50    0.50    --  -38.50 125.00  60.00  100
 28  ω    -90.00 -60.00   0.50    0.50    --  -38.50 125.00  60.00   60
 29  ω   -108.00 -13.00   0.50    0.50    --  -38.50 -50.00-100.00  190
 30  ω     45.00  87.00   0.50    2.00    --  111.00-125.00 150.00   84
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0689504000
_diffrn_orient_matrix_UB_12      0.1130292000
_diffrn_orient_matrix_UB_13      0.1083143000
_diffrn_orient_matrix_UB_21      -0.1475998000
_diffrn_orient_matrix_UB_22      -0.0579011000
_diffrn_orient_matrix_UB_23      0.0628458000
_diffrn_orient_matrix_UB_31      0.1003654000
_diffrn_orient_matrix_UB_32      -0.1628803000
_diffrn_orient_matrix_UB_33      0.0528132000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.831
_reflns_Friedel_fraction_full    0.991
_reflns_Friedel_fraction_max     0.968
_reflns_number_gt                2820
_reflns_number_total             2836
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_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 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_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         0.181
_refine_diff_density_min         -0.293
_refine_diff_density_rms         0.059
_refine_ls_abs_structure_details 
;
 Flack x determined using 1269 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.224(7)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         2836
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0233
_refine_ls_R_factor_gt           0.0231
_refine_ls_restrained_S_all      1.092
_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)+(0.0362P)²+0.1976P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0604
_refine_ls_wR_factor_ref         0.0606
_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.a Riding coordinates:
 N1(H1)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C8(H8), C9(H9), C11(H11), C12(H12)
2.c Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.42190(6) 0.71702(7) 0.14444(4) 0.01160(12) Uani 1 1 d . . . . .
S2 S 0.47495(6) 0.37057(7) 0.26310(4) 0.01329(13) Uani 1 1 d . . . . .
O1 O 0.5092(2) 0.8023(2) 0.05842(15) 0.0172(3) Uani 1 1 d . . . . .
O2 O 0.4397(2) 0.7811(2) 0.26297(14) 0.0162(3) Uani 1 1 d . . . . .
O3 O 0.3251(2) 0.4068(2) 0.31134(15) 0.0189(4) Uani 1 1 d . . . . .
O4 O 0.4998(2) 0.1975(2) 0.21391(15) 0.0201(3) Uani 1 1 d . . . . .
O5 O 1.0426(2) 0.4892(2) 0.62849(14) 0.0175(3) Uani 1 1 d . . . . .
N1 N 0.4925(2) 0.5090(2) 0.15083(16) 0.0136(4) Uani 1 1 d . . . . .
H1 H 0.5062 0.4608 0.0816 0.016 Uiso 1 1 d R . . . .
C1 C 0.2108(3) 0.7034(3) 0.08590(19) 0.0141(4) Uani 1 1 d . . . . .
C2 C 0.0906(3) 0.7157(3) 0.16131(19) 0.0168(4) Uani 1 1 d . . . . .
H2 H 0.1207 0.7299 0.2421 0.020 Uiso 1 1 calc R . . . .
C3 C -0.0755(3) 0.7063(4) 0.1131(2) 0.0198(5) Uani 1 1 d . . . . .
H3 H -0.1581 0.7160 0.1617 0.024 Uiso 1 1 calc R . . . .
C4 C -0.1188(3) 0.6824(3) -0.0079(2) 0.0199(5) Uani 1 1 d . . . . .
H4 H -0.2302 0.6756 -0.0395 0.024 Uiso 1 1 calc R . . . .
C5 C 0.0032(3) 0.6684(3) -0.0818(2) 0.0199(5) Uani 1 1 d . . . . .
H5 H -0.0269 0.6521 -0.1624 0.024 Uiso 1 1 calc R . . . .
C6 C 0.1702(3) 0.6789(3) -0.0353(2) 0.0172(5) Uani 1 1 d . . . . .
H6 H 0.2528 0.6697 -0.0839 0.021 Uiso 1 1 calc R . . . .
C7 C 0.6459(3) 0.4235(3) 0.3675(2) 0.0138(4) Uani 1 1 d . . . . .
C8 C 0.8047(3) 0.4078(3) 0.3368(2) 0.0159(4) Uani 1 1 d . . . . .
H8 H 0.8192 0.3816 0.2594 0.019 Uiso 1 1 calc R . . . .
C9 C 0.9421(3) 0.4312(3) 0.4217(2) 0.0158(4) Uani 1 1 d . . . . .
H9 H 1.0489 0.4206 0.4017 0.019 Uiso 1 1 calc R . . . .
C10 C 0.9182(3) 0.4708(3) 0.53758(19) 0.0139(4) Uani 1 1 d . . . . .
C11 C 0.7575(3) 0.4925(3) 0.5669(2) 0.0159(4) Uani 1 1 d . . . . .
H11 H 0.7424 0.5235 0.6435 0.019 Uiso 1 1 calc R . . . .
C12 C 0.6214(3) 0.4681(3) 0.4821(2) 0.0157(4) Uani 1 1 d . . . . .
H12 H 0.5144 0.4813 0.5014 0.019 Uiso 1 1 calc R . . . .
C13 C 1.2090(3) 0.4610(4) 0.6036(2) 0.0219(5) Uani 1 1 d . . . . .
H13A H 1.2354 0.5488 0.5476 0.033 Uiso 1 1 calc GR . . . .
H13B H 1.2181 0.3431 0.5714 0.033 Uiso 1 1 calc GR . . . .
H13C H 1.2850 0.4723 0.6751 0.033 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O1 1.4367(17) . ?
S1 O2 1.4268(16) . ?
S1 N1 1.6528(19) . ?
S1 C1 1.758(2) . ?
S2 O3 1.4285(17) . ?
S2 O4 1.4334(18) . ?
S2 N1 1.6688(19) . ?
S2 C7 1.751(2) . ?
O5 C10 1.356(3) . ?
O5 C13 1.434(3) . ?
N1 H1 0.8897 . ?
C1 C2 1.390(3) . ?
C1 C6 1.393(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.389(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.393(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.390(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.391(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.387(3) . ?
C7 C12 1.393(3) . ?
C8 H8 0.9300 . ?
C8 C9 1.389(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.397(3) . ?
C10 C11 1.400(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.381(3) . ?
C12 H12 0.9300 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 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 104.23(10) . . ?
O1 S1 C1 108.11(10) . . ?
O2 S1 O1 120.41(11) . . ?
O2 S1 N1 106.41(10) . . ?
O2 S1 C1 110.53(10) . . ?
N1 S1 C1 106.10(11) . . ?
O3 S2 O4 119.64(10) . . ?
O3 S2 N1 110.22(10) . . ?
O3 S2 C7 109.43(11) . . ?
O4 S2 N1 102.93(10) . . ?
O4 S2 C7 109.29(10) . . ?
N1 S2 C7 104.12(10) . . ?
C10 O5 C13 117.26(18) . . ?
S1 N1 S2 123.36(11) . . ?
S1 N1 H1 115.1 . . ?
S2 N1 H1 118.0 . . ?
C2 C1 S1 119.36(17) . . ?
C2 C1 C6 122.3(2) . . ?
C6 C1 S1 118.37(16) . . ?
C1 C2 H2 120.8 . . ?
C3 C2 C1 118.4(2) . . ?
C3 C2 H2 120.8 . . ?
C2 C3 H3 119.9 . . ?
C2 C3 C4 120.2(2) . . ?
C4 C3 H3 119.9 . . ?
C3 C4 H4 119.7 . . ?
C5 C4 C3 120.6(2) . . ?
C5 C4 H4 119.7 . . ?
C4 C5 H5 120.0 . . ?
C4 C5 C6 120.1(2) . . ?
C6 C5 H5 120.0 . . ?
C1 C6 H6 120.8 . . ?
C5 C6 C1 118.5(2) . . ?
C5 C6 H6 120.8 . . ?
C8 C7 S2 119.18(17) . . ?
C8 C7 C12 120.9(2) . . ?
C12 C7 S2 119.73(17) . . ?
C7 C8 H8 120.0 . . ?
C7 C8 C9 120.0(2) . . ?
C9 C8 H8 120.0 . . ?
C8 C9 H9 120.4 . . ?
C8 C9 C10 119.3(2) . . ?
C10 C9 H9 120.4 . . ?
O5 C10 C9 124.4(2) . . ?
O5 C10 C11 115.30(19) . . ?
C9 C10 C11 120.3(2) . . ?
C10 C11 H11 120.0 . . ?
C12 C11 C10 120.1(2) . . ?
C12 C11 H11 120.0 . . ?
C7 C12 H12 120.3 . . ?
C11 C12 C7 119.4(2) . . ?
C11 C12 H12 120.3 . . ?
O5 C13 H13A 109.5 . . ?
O5 C13 H13B 109.5 . . ?
O5 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.397
_oxdiff_exptl_absorpt_empirical_full_min 0.848
####################################################################### 
# 
# 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_24e
_database_code_depnum_ccdc_archive 'CCDC 2051056'
loop_
_audit_author_name
_audit_author_address
'Felix Hennersdorf'
;TU Dresden
Germany
;
_audit_update_record             
;
2020-12-17 deposited with the CCDC.	2021-04-01 downloaded from the CCDC.
;
_audit_creation_date             2020-12-16
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H10 F N O4 S2'
_chemical_formula_sum            'C12 H10 F N O4 S2'
_chemical_formula_weight         315.33
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C84 H72 F8 N8 O44 S16 '
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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                   15.93411(17)
_cell_length_b                   11.15685(12)
_cell_length_c                   14.40620(14)
_cell_angle_alpha                90
_cell_angle_beta                 99.6810(10)
_cell_angle_gamma                90
_cell_volume                     2524.58(5)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    16772
_cell_measurement_temperature    100.0(4)
_cell_measurement_theta_max      76.4000
_cell_measurement_theta_min      5.0270
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    4.092
_exptl_absorpt_correction_T_max  0.902
_exptl_absorpt_correction_T_min  0.545
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.659
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1296
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
4 7 0 0.0451
-4 -7 0 0.0563
-1 -1 -9 0.0795
-3 -6 6 0.0800
10 0 0 0.0177
-10 0 0 0.0097
7 -5 1 0.0475
-6 5 -1 0.0411
-10 -2 3 0.0385
-3 2 9 0.1138
2 1 9 0.1090
9 -1 3 0.0418
10 -2 -2 0.0237

_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.114
_exptl_crystal_size_min          0.027
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
4.0032 6.9963 -0.0078 -0.0567 0.0978 1.0366
-4.0032 -6.9963 0.0078 0.0567 -0.0978 -1.0366
-0.9897 -1.0040 -8.9912 0.6015 -0.7974 -0.1190
-3.0100 -5.9938 6.0017 -0.3589 0.4332 -0.9028
9.9882 -0.0009 0.0059 -0.8364 -0.3625 0.3587
-9.9882 0.0009 -0.0059 0.8364 0.3625 -0.3587
6.9850 -4.9977 1.0106 -0.8458 -0.3385 -0.3918
-5.9862 4.9976 -1.0100 0.7622 0.3022 0.4277
-9.9939 -1.9966 2.9943 0.5711 0.5595 -0.6287
-3.0044 2.0039 8.9873 -0.2273 0.9771 0.1031
1.9886 1.0040 8.9917 -0.6851 0.7611 0.1549
8.9849 -0.9988 3.0041 -0.9783 -0.0947 0.1804
9.9883 -2.0010 -1.9894 -0.7918 -0.6095 0.1134

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0277
_diffrn_reflns_av_unetI/netI     0.0230
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            29126
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.690
_diffrn_reflns_theta_min         2.813
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.0(4)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2850
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     16.00 111.00   0.50    3.00    --   42.50  57.00  90.00  190
  2  ω     83.00 110.00   0.50   12.00    --  111.00  61.00  90.00   54
  3  ω    118.00 172.00   0.50   12.00    --  111.00  77.00  60.00  108
  4  ω    153.00 178.00   0.50   12.00    --  111.00  61.00  90.00   50
  5  ω    146.00 173.00   0.50   12.00    --  111.00  77.00   0.00   54
  6  ω    144.00 173.00   0.50   12.00    --  111.00  45.00   0.00   58
  7  ω    135.00 164.00   0.50   12.00    --  111.00  61.00  30.00   58
  8  ω    124.00 174.00   0.50   12.00    --  111.00  77.00 -30.00  100
  9  ω    129.00 178.00   0.50   12.00    --  111.00  45.00 120.00   98
 10  ω     87.00 115.00   0.50   12.00    --  111.00  30.00   0.00   56
 11  ω     88.00 116.00   0.50   12.00    --  111.00  45.00  30.00   56
 12  ω     89.00 116.00   0.50   12.00    --  111.00  45.00  60.00   54
 13  ω     89.00 118.00   0.50   12.00    --  111.00  30.00  30.00   58
 14  ω     83.00 111.00   0.50   12.00    --  111.00  61.00  30.00   56
 15  ω     89.00 165.00   0.50   12.00    --  111.00  30.00  60.00  152
 16  ω     89.00 118.00   0.50   12.00    --  111.00  45.00 120.00   58
 17  ω     83.00 110.00   0.50   12.00    --  111.00  61.00  60.00   54
 18  ω     87.00 113.00   0.50   12.00    --  111.00  45.00  90.00   52
 19  ω     88.00 116.00   0.50   12.00    --  111.00  30.00 120.00   56
 20  ω     87.00 115.00   0.50   12.00    --  111.00  30.00  90.00   56
 21  ω     80.00 107.00   0.50   12.00    --  111.00  77.00  60.00   54
 22  ω     80.00 106.00   0.50   12.00    --  111.00  77.00  30.00   52
 23  ω     83.00 110.00   0.50   12.00    --  111.00  61.00   0.00   54
 24  ω     88.00 113.00   0.50   12.00    --  111.00  45.00 -30.00   50
 25  ω     87.00 114.00   0.50   12.00    --  111.00  45.00   0.00   54
 26  ω     80.00 107.00   0.50   12.00    --  111.00  77.00 -30.00   54
 27  ω     80.00 108.00   0.50   12.00    --  111.00  77.00   0.00   56
 28  ω     83.00 111.00   0.50   12.00    --  111.00  61.00 -30.00   56
 29  ω     80.00 107.00   0.50   12.00    --  111.00  77.00  90.00   54
 30  ω     23.00  70.00   0.50    3.00    --   42.50  57.00  60.00   94
 31  ω     19.00  55.00   0.50    3.00    --   42.50  19.00  60.00   72
 32  ω     21.00 101.00   0.50    3.00    --   42.50  38.00  60.00  160
 33  ω     67.00 140.00   0.50   12.00    --  111.00 -77.00-120.00  146
 34  ω     80.00 178.00   0.50   12.00    --  111.00  15.00-150.00  196
 35  ω     64.00 105.00   0.50   12.00    --  111.00 -94.00-120.00   82
 36  ω     40.00 130.00   0.50   12.00    --  111.00 -45.00-150.00  180
 37  ω     52.00  79.00   0.50   12.00    --  111.00 -94.00  30.00   54
 38  ω     48.00 101.00   0.50   12.00    --  111.00 -94.00  60.00  106
 39  ω     50.00  92.00   0.50   12.00    --  111.00 -94.00 150.00   84
 40  ω     40.00  65.00   0.50   12.00    --  111.00 -94.00  90.00   50
 41  ω    -28.00  59.00   0.50    3.00    --   42.50 -77.00  30.00  174
 42  ω     35.00  60.00   0.50   12.00    --  111.00 -94.00-120.00   50
 43  ω     42.00 107.00   0.50   12.00    --  111.00 -94.00-180.00  130
 44  ω    -59.00  33.00   0.50    3.00    --  -38.50  38.00-180.00  184
 45  ω    -90.00 -57.00   0.50    3.00    --  -38.50 -38.00-180.00   66
 46  ω   -111.00 -61.00   0.50    3.00    --  -38.50 -38.00-120.00  100
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0836946000
_diffrn_orient_matrix_UB_12      0.0397081000
_diffrn_orient_matrix_UB_13      -0.0621190000
_diffrn_orient_matrix_UB_21      -0.0363467000
_diffrn_orient_matrix_UB_22      0.0348818000
_diffrn_orient_matrix_UB_23      0.0887932000
_diffrn_orient_matrix_UB_31      0.0359275000
_diffrn_orient_matrix_UB_32      0.1276048000
_diffrn_orient_matrix_UB_33      -0.0049708000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5113
_reflns_number_total             5280
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_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 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_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         0.903
_refine_diff_density_min         -0.559
_refine_diff_density_rms         0.079
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.128
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     374
_refine_ls_number_reflns         5280
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0362
_refine_ls_R_factor_gt           0.0351
_refine_ls_restrained_S_all      1.128
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0332P)²+3.5911P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0904
_refine_ls_wR_factor_ref         0.0911
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 F1C-C8B \\sim F1B-C2B
 with sigma of 0.001
3. Others
 Sof(H2B)=Sof(F1C)=1-FVAR(1)
 Sof(H8B)=Sof(F1B)=FVAR(1)
4.a Aromatic/amide H refined with riding coordinates:
 C3A(H3A), C4A(H4A), C5A(H5A), C6A(H6A), C8A(H8A), C9A(H9A), C10A(H10A),
 C11A(H11A), C12A(H12A), C2B(H2B), C3B(H3B), C4B(H4B), C5B(H5B), C6B(H6B),
 C8B(H8B), C9B(H9B), C10B(H10B), C11B(H11B), C12B(H12B)
;
_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
S1A S 1.01073(3) 0.29127(4) 0.50206(3) 0.01402(11) Uani 1 1 d . . . . .
S2A S 1.04399(3) 0.32371(4) 0.30650(3) 0.01403(11) Uani 1 1 d . . . . .
F1A F 0.85311(8) 0.43016(11) 0.44044(10) 0.0249(3) Uani 1 1 d . . . . .
O1A O 1.06777(9) 0.19267(13) 0.52023(11) 0.0206(3) Uani 1 1 d . . . . .
O2A O 1.00732(9) 0.37864(13) 0.57441(10) 0.0189(3) Uani 1 1 d . . . . .
O3A O 1.07723(9) 0.20501(13) 0.31750(11) 0.0197(3) Uani 1 1 d . . . . .
O4A O 1.08966(9) 0.41720(13) 0.26886(10) 0.0201(3) Uani 1 1 d . . . . .
N1A N 1.03650(10) 0.37219(15) 0.41467(12) 0.0152(3) Uani 1 1 d . . . . .
C1A C 0.90808(12) 0.23427(17) 0.46153(14) 0.0145(4) Uani 1 1 d . . . . .
C2A C 0.83940(13) 0.31099(17) 0.43513(14) 0.0158(4) Uani 1 1 d . . . . .
C3A C 0.75900(13) 0.2685(2) 0.40337(15) 0.0199(4) Uani 1 1 d . . . . .
H3A H 0.713687 0.320952 0.386225 0.024 Uiso 1 1 calc R . . . .
C4A C 0.74672(13) 0.1451(2) 0.39736(15) 0.0220(4) Uani 1 1 d . . . . .
H4A H 0.692490 0.114791 0.376314 0.026 Uiso 1 1 calc R . . . .
C5A C 0.81418(14) 0.06689(19) 0.42231(15) 0.0227(4) Uani 1 1 d . . . . .
H5A H 0.805089 -0.015378 0.417435 0.027 Uiso 1 1 calc R . . . .
C6A C 0.89537(13) 0.11085(18) 0.45460(15) 0.0189(4) Uani 1 1 d . . . . .
H6A H 0.940778 0.058455 0.471425 0.023 Uiso 1 1 calc R . . . .
C7A C 0.93913(12) 0.31900(18) 0.24463(14) 0.0155(4) Uani 1 1 d . . . . .
C8A C 0.89939(14) 0.42692(19) 0.21524(15) 0.0217(4) Uani 1 1 d . . . . .
H8A H 0.927720 0.499552 0.227535 0.026 Uiso 1 1 calc R . . . .
C9A C 0.81632(15) 0.4230(2) 0.16709(16) 0.0287(5) Uani 1 1 d . . . . .
H9A H 0.788373 0.493797 0.146524 0.034 Uiso 1 1 calc R . . . .
C10A C 0.77490(14) 0.3142(3) 0.14956(16) 0.0297(5) Uani 1 1 d . . . . .
H10A H 0.719268 0.312417 0.117157 0.036 Uiso 1 1 calc R . . . .
C11A C 0.81556(14) 0.2078(2) 0.17985(16) 0.0261(5) Uani 1 1 d . . . . .
H11A H 0.787007 0.135319 0.167957 0.031 Uiso 1 1 calc R . . . .
C12A C 0.89882(13) 0.20927(19) 0.22790(14) 0.0190(4) Uani 1 1 d . . . . .
H12A H 0.926732 0.138416 0.248289 0.023 Uiso 1 1 calc R . . . .
S1B S 0.51887(3) 0.20384(4) 0.47694(3) 0.01511(11) Uani 1 1 d . . . . .
S2B S 0.53846(3) 0.22280(4) 0.68515(3) 0.01643(11) Uani 1 1 d . . . . .
O1B O 0.58043(9) 0.29522(14) 0.47192(11) 0.0219(3) Uani 1 1 d . . . . .
O2B O 0.51651(9) 0.10053(14) 0.41716(10) 0.0206(3) Uani 1 1 d . . . . .
O3B O 0.57766(9) 0.33545(14) 0.67343(11) 0.0218(3) Uani 1 1 d . . . . .
O4B O 0.57591(10) 0.13953(15) 0.75546(11) 0.0259(3) Uani 1 1 d . . . . .
N1B N 0.53552(11) 0.14669(17) 0.58458(12) 0.0170(3) Uani 1 1 d . . . . .
C1B C 0.41824(12) 0.27168(18) 0.46327(13) 0.0145(4) Uani 1 1 d . . . . .
C2B C 0.34579(13) 0.20494(17) 0.47023(14) 0.0159(4) Uani 1 1 d D . . . .
H2B H 0.350242 0.122302 0.478002 0.019 Uiso 0.121(4) 1 calc R . P A 2
C3B C 0.26748(13) 0.25930(19) 0.46579(14) 0.0192(4) Uani 1 1 d . . . . .
H3B H 0.219249 0.214191 0.470289 0.023 Uiso 1 1 calc R . . . .
C4B C 0.26216(13) 0.3830(2) 0.45446(15) 0.0224(4) Uani 1 1 d . . . . .
H4B H 0.209908 0.420995 0.452302 0.027 Uiso 1 1 calc R . . . .
C5B C 0.33353(14) 0.45061(19) 0.44633(15) 0.0225(4) Uani 1 1 d . . . . .
H5B H 0.328831 0.533192 0.438336 0.027 Uiso 1 1 calc R . . . .
C6B C 0.41207(13) 0.39516(18) 0.45009(14) 0.0183(4) Uani 1 1 d . . . . .
H6B H 0.460001 0.440029 0.443881 0.022 Uiso 1 1 calc R . . . .
C7B C 0.43186(12) 0.24697(19) 0.69712(13) 0.0169(4) Uani 1 1 d . . . . .
C8B C 0.38141(15) 0.1495(2) 0.71299(15) 0.0238(4) Uani 1 1 d D . . . .
H8B H 0.403703 0.072286 0.716802 0.029 Uiso 0.879(4) 1 calc R . P A 1
C9B C 0.29787(15) 0.1693(2) 0.72297(16) 0.0289(5) Uani 1 1 d . . . . .
H9B H 0.263386 0.105074 0.733311 0.035 Uiso 1 1 calc R . . . .
C10B C 0.26530(15) 0.2850(3) 0.71759(17) 0.0319(6) Uani 1 1 d . . . . .
H10B H 0.208843 0.297859 0.723802 0.038 Uiso 1 1 calc R . . . .
C11B C 0.31650(15) 0.3815(2) 0.70300(17) 0.0289(5) Uani 1 1 d . . . . .
H11B H 0.294390 0.458808 0.700368 0.035 Uiso 1 1 calc R . . . .
C12B C 0.40044(14) 0.3632(2) 0.69231(15) 0.0215(4) Uani 1 1 d . . . . .
H12B H 0.434938 0.427526 0.682153 0.026 Uiso 1 1 calc R . . . .
F1B F 0.35254(9) 0.08618(12) 0.48302(10) 0.0218(4) Uani 0.879(4) 1 d D . P A 1
F1C F 0.4061(9) 0.0353(5) 0.7086(11) 0.049(4) Uiso 0.121(4) 1 d D . P A 2
H1A H 1.0240(18) 0.441(3) 0.417(2) 0.027(7) Uiso 1 1 d . . . . .
H1B H 0.5242(18) 0.080(3) 0.588(2) 0.027(8) 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
S1A O1A 1.4230(15) . ?
S1A O2A 1.4349(14) . ?
S1A N1A 1.6561(17) . ?
S1A C1A 1.7605(19) . ?
S2A O3A 1.4252(14) . ?
S2A O4A 1.4298(15) . ?
S2A N1A 1.6726(17) . ?
S2A C7A 1.757(2) . ?
F1A C2A 1.348(2) . ?
N1A H1A 0.79(3) . ?
C1A C2A 1.391(3) . ?
C1A C6A 1.393(3) . ?
C2A C3A 1.370(3) . ?
C3A H3A 0.9300 . ?
C3A C4A 1.391(3) . ?
C4A H4A 0.9300 . ?
C4A C5A 1.384(3) . ?
C5A H5A 0.9300 . ?
C5A C6A 1.389(3) . ?
C6A H6A 0.9300 . ?
C7A C8A 1.393(3) . ?
C7A C12A 1.385(3) . ?
C8A H8A 0.9300 . ?
C8A C9A 1.388(3) . ?
C9A H9A 0.9300 . ?
C9A C10A 1.385(4) . ?
C10A H10A 0.9300 . ?
C10A C11A 1.387(4) . ?
C11A H11A 0.9300 . ?
C11A C12A 1.390(3) . ?
C12A H12A 0.9300 . ?
S1B O1B 1.4250(15) . ?
S1B O2B 1.4356(15) . ?
S1B N1B 1.6563(18) . ?
S1B C1B 1.7539(19) . ?
S2B O3B 1.4261(16) . ?
S2B O4B 1.4288(16) . ?
S2B N1B 1.6732(18) . ?
S2B C7B 1.757(2) . ?
N1B H1B 0.77(3) . ?
C1B C2B 1.392(3) . ?
C1B C6B 1.392(3) . ?
C2B H2B 0.9300 . ?
C2B C3B 1.379(3) . ?
C2B F1B 1.340(2) . ?
C3B H3B 0.9300 . ?
C3B C4B 1.391(3) . ?
C4B H4B 0.9300 . ?
C4B C5B 1.386(3) . ?
C5B H5B 0.9300 . ?
C5B C6B 1.389(3) . ?
C6B H6B 0.9300 . ?
C7B C8B 1.394(3) . ?
C7B C12B 1.388(3) . ?
C8B H8B 0.9300 . ?
C8B C9B 1.380(3) . ?
C8B F1C 1.338(3) . ?
C9B H9B 0.9300 . ?
C9B C10B 1.388(4) . ?
C10B H10B 0.9300 . ?
C10B C11B 1.388(4) . ?
C11B H11B 0.9300 . ?
C11B C12B 1.387(3) . ?
C12B H12B 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
O1A S1A O2A 119.51(9) . . ?
O1A S1A N1A 109.20(9) . . ?
O1A S1A C1A 108.12(9) . . ?
O2A S1A N1A 103.08(9) . . ?
O2A S1A C1A 109.86(9) . . ?
N1A S1A C1A 106.27(9) . . ?
O3A S2A O4A 121.11(9) . . ?
O3A S2A N1A 106.28(9) . . ?
O3A S2A C7A 109.42(9) . . ?
O4A S2A N1A 103.77(9) . . ?
O4A S2A C7A 109.31(9) . . ?
N1A S2A C7A 105.75(9) . . ?
S1A N1A S2A 126.70(11) . . ?
S1A N1A H1A 114(2) . . ?
S2A N1A H1A 114(2) . . ?
C2A C1A S1A 120.85(15) . . ?
C2A C1A C6A 119.38(18) . . ?
C6A C1A S1A 119.77(15) . . ?
F1A C2A C1A 118.62(17) . . ?
F1A C2A C3A 119.60(18) . . ?
C3A C2A C1A 121.78(19) . . ?
C2A C3A H3A 120.8 . . ?
C2A C3A C4A 118.49(19) . . ?
C4A C3A H3A 120.8 . . ?
C3A C4A H4A 119.6 . . ?
C5A C4A C3A 120.85(19) . . ?
C5A C4A H4A 119.6 . . ?
C4A C5A H5A 119.9 . . ?
C4A C5A C6A 120.2(2) . . ?
C6A C5A H5A 119.9 . . ?
C1A C6A H6A 120.4 . . ?
C5A C6A C1A 119.28(19) . . ?
C5A C6A H6A 120.4 . . ?
C8A C7A S2A 118.25(16) . . ?
C12A C7A S2A 119.23(16) . . ?
C12A C7A C8A 122.52(19) . . ?
C7A C8A H8A 120.9 . . ?
C9A C8A C7A 118.1(2) . . ?
C9A C8A H8A 120.9 . . ?
C8A C9A H9A 119.9 . . ?
C10A C9A C8A 120.2(2) . . ?
C10A C9A H9A 119.9 . . ?
C9A C10A H10A 119.7 . . ?
C9A C10A C11A 120.6(2) . . ?
C11A C10A H10A 119.7 . . ?
C10A C11A H11A 119.9 . . ?
C10A C11A C12A 120.2(2) . . ?
C12A C11A H11A 119.9 . . ?
C7A C12A C11A 118.2(2) . . ?
C7A C12A H12A 120.9 . . ?
C11A C12A H12A 120.9 . . ?
O1B S1B O2B 119.52(9) . . ?
O1B S1B N1B 108.65(9) . . ?
O1B S1B C1B 108.04(9) . . ?
O2B S1B N1B 103.68(9) . . ?
O2B S1B C1B 110.36(9) . . ?
N1B S1B C1B 105.71(9) . . ?
O3B S2B O4B 121.19(10) . . ?
O3B S2B N1B 107.08(9) . . ?
O3B S2B C7B 109.04(10) . . ?
O4B S2B N1B 103.38(9) . . ?
O4B S2B C7B 109.01(10) . . ?
N1B S2B C7B 106.03(9) . . ?
S1B N1B S2B 126.31(12) . . ?
S1B N1B H1B 116(2) . . ?
S2B N1B H1B 114(2) . . ?
C2B C1B S1B 120.99(15) . . ?
C2B C1B C6B 119.94(18) . . ?
C6B C1B S1B 118.99(15) . . ?
C1B C2B H2B 119.5 . . ?
C3B C2B C1B 121.09(19) . . ?
C3B C2B H2B 119.5 . . ?
F1B C2B C1B 119.39(18) . . ?
F1B C2B C3B 119.51(18) . . ?
C2B C3B H3B 120.7 . . ?
C2B C3B C4B 118.60(19) . . ?
C4B C3B H3B 120.7 . . ?
C3B C4B H4B 119.5 . . ?
C5B C4B C3B 121.01(19) . . ?
C5B C4B H4B 119.5 . . ?
C4B C5B H5B 120.0 . . ?
C4B C5B C6B 120.1(2) . . ?
C6B C5B H5B 120.0 . . ?
C1B C6B H6B 120.4 . . ?
C5B C6B C1B 119.26(19) . . ?
C5B C6B H6B 120.4 . . ?
C8B C7B S2B 119.35(17) . . ?
C12B C7B S2B 119.03(16) . . ?
C12B C7B C8B 121.6(2) . . ?
C7B C8B H8B 120.5 . . ?
C9B C8B C7B 119.0(2) . . ?
C9B C8B H8B 120.5 . . ?
F1C C8B C7B 123.6(7) . . ?
F1C C8B C9B 117.0(7) . . ?
C8B C9B H9B 120.0 . . ?
C8B C9B C10B 120.1(2) . . ?
C10B C9B H9B 120.0 . . ?
C9B C10B H10B 119.8 . . ?
C11B C10B C9B 120.4(2) . . ?
C11B C10B H10B 119.8 . . ?
C10B C11B H11B 119.8 . . ?
C12B C11B C10B 120.3(2) . . ?
C12B C11B H11B 119.8 . . ?
C7B C12B H12B 120.7 . . ?
C11B C12B C7B 118.6(2) . . ?
C11B C12B H12B 120.7 . . ?

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
S1A C1A C2A F1A 0.5(3) . . . . ?
S1A C1A C2A C3A 179.98(16) . . . . ?
S1A C1A C6A C5A -179.83(16) . . . . ?
S2A C7A C8A C9A -179.46(16) . . . . ?
S2A C7A C12A C11A 179.23(16) . . . . ?
F1A C2A C3A C4A 179.16(18) . . . . ?
O1A S1A N1A S2A 56.44(15) . . . . ?
O1A S1A C1A C2A -177.88(16) . . . . ?
O1A S1A C1A C6A 1.33(19) . . . . ?
O2A S1A N1A S2A -175.50(12) . . . . ?
O2A S1A C1A C2A 50.11(19) . . . . ?
O2A S1A C1A C6A -130.68(16) . . . . ?
O3A S2A N1A S1A -35.88(15) . . . . ?
O3A S2A C7A C8A -171.29(16) . . . . ?
O3A S2A C7A C12A 9.49(19) . . . . ?
O4A S2A N1A S1A -164.62(12) . . . . ?
O4A S2A C7A C8A -36.53(19) . . . . ?
O4A S2A C7A C12A 144.24(16) . . . . ?
N1A S1A C1A C2A -60.75(18) . . . . ?
N1A S1A C1A C6A 118.46(17) . . . . ?
N1A S2A C7A C8A 74.62(18) . . . . ?
N1A S2A C7A C12A -104.61(17) . . . . ?
C1A S1A N1A S2A -59.96(14) . . . . ?
C1A C2A C3A C4A -0.3(3) . . . . ?
C2A C1A C6A C5A -0.6(3) . . . . ?
C2A C3A C4A C5A -0.4(3) . . . . ?
C3A C4A C5A C6A 0.5(3) . . . . ?
C4A C5A C6A C1A 0.0(3) . . . . ?
C6A C1A C2A F1A -178.67(18) . . . . ?
C6A C1A C2A C3A 0.8(3) . . . . ?
C7A S2A N1A S1A 80.37(14) . . . . ?
C7A C8A C9A C10A 0.2(3) . . . . ?
C8A C7A C12A C11A 0.0(3) . . . . ?
C8A C9A C10A C11A 0.1(3) . . . . ?
C9A C10A C11A C12A -0.3(3) . . . . ?
C10A C11A C12A C7A 0.3(3) . . . . ?
C12A C7A C8A C9A -0.3(3) . . . . ?
S1B C1B C2B C3B 175.62(16) . . . . ?
S1B C1B C2B F1B -3.3(3) . . . . ?
S1B C1B C6B C5B -175.19(15) . . . . ?
S2B C7B C8B C9B 179.55(16) . . . . ?
S2B C7B C8B F1C -8.3(8) . . . . ?
S2B C7B C12B C11B -179.22(17) . . . . ?
O1B S1B N1B S2B 55.94(15) . . . . ?
O1B S1B C1B C2B -176.48(16) . . . . ?
O1B S1B C1B C6B 0.21(19) . . . . ?
O2B S1B N1B S2B -175.94(12) . . . . ?
O2B S1B C1B C2B 51.17(19) . . . . ?
O2B S1B C1B C6B -132.14(16) . . . . ?
O3B S2B N1B S1B -36.44(15) . . . . ?
O3B S2B C7B C8B -177.62(16) . . . . ?
O3B S2B C7B C12B 1.14(19) . . . . ?
O4B S2B N1B S1B -165.49(13) . . . . ?
O4B S2B C7B C8B -43.32(19) . . . . ?
O4B S2B C7B C12B 135.44(16) . . . . ?
N1B S1B C1B C2B -60.32(18) . . . . ?
N1B S1B C1B C6B 116.37(17) . . . . ?
N1B S2B C7B C8B 67.39(18) . . . . ?
N1B S2B C7B C12B -113.85(17) . . . . ?
C1B S1B N1B S2B -59.81(15) . . . . ?
C1B C2B C3B C4B -0.2(3) . . . . ?
C2B C1B C6B C5B 1.5(3) . . . . ?
C2B C3B C4B C5B 1.0(3) . . . . ?
C3B C4B C5B C6B -0.5(3) . . . . ?
C4B C5B C6B C1B -0.8(3) . . . . ?
C6B C1B C2B C3B -1.0(3) . . . . ?
C6B C1B C2B F1B -179.92(18) . . . . ?
C7B S2B N1B S1B 79.88(15) . . . . ?
C7B C8B C9B C10B -0.3(3) . . . . ?
C8B C7B C12B C11B -0.5(3) . . . . ?
C8B C9B C10B C11B -0.6(3) . . . . ?
C9B C10B C11B C12B 0.9(4) . . . . ?
C10B C11B C12B C7B -0.4(3) . . . . ?
C12B C7B C8B C9B 0.8(3) . . . . ?
C12B C7B C8B F1C 172.9(8) . . . . ?
F1B C2B C3B C4B 178.67(19) . . . . ?
F1C C8B C9B C10B -172.9(8) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.733
_oxdiff_exptl_absorpt_empirical_full_min 0.778
####################################################################### 
# 
# 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_23c
_database_code_depnum_ccdc_archive 'CCDC 2051052'
loop_
_audit_author_name
_audit_author_address
'Felix Hennersdorf'
;TU Dresden
Germany
;
_audit_update_record             
;
2020-12-17 deposited with the CCDC.	2021-04-01 downloaded from the CCDC.
;
_audit_creation_date             2017-09-20
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C9 H11 F N2 O2 S'
_chemical_formula_sum            'C9 H11 F N2 O2 S'
_chemical_formula_weight         230.26
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C36 H44 F4 N8 O8 S4 '
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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                   9.8618(4)
_cell_length_b                   13.77947(14)
_cell_length_c                   12.7595(6)
_cell_angle_alpha                90
_cell_angle_beta                 144.027(10)
_cell_angle_gamma                90
_cell_volume                     1018.50(16)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3464
_cell_measurement_temperature    99.99(10)
_cell_measurement_theta_max      76.1290
_cell_measurement_theta_min      5.5100
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.843
_exptl_absorpt_correction_T_max  0.915
_exptl_absorpt_correction_T_min  0.761
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.502
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             480
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-5 -5 5 0.0245
6 4 -6 0.0184
4 -6 -6 0.0354
-4 6 6 0.0508
-6 -1 7 0.0314
-2 3 6 0.0624
2 -1 -7 0.0719
1 3 -6 0.0738
-2 9 2 0.0495
2 -9 -2 0.0231
-6 2 6 0.0241
-6 -3 5 0.0311
5 -5 -5 0.0141

_exptl_crystal_size_max          0.159
_exptl_crystal_size_mid          0.078
_exptl_crystal_size_min          0.042
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-4.9921 -5.0003 4.9911 -0.0311 0.9198 0.2769
5.9923 4.0012 -5.9913 0.0983 -1.0265 -0.1317
4.0029 -5.9960 -6.0017 -0.0593 -0.3800 0.9108
-4.0029 5.9960 6.0017 0.0593 0.3800 -0.9108
-5.9952 -1.0022 6.9937 0.0047 0.9258 -0.2339
-2.0018 2.9989 5.9987 0.6127 0.2358 -0.6494
2.0001 -1.0000 -6.9960 -0.8679 -0.3284 0.5135
0.9972 2.9978 -5.9927 -1.0263 -0.3376 0.0674
-2.0067 8.9952 2.0077 -0.3473 -0.0571 -0.9926
2.0067 -8.9952 -2.0077 0.3473 0.0571 0.9926
-5.9977 1.9962 5.9975 -0.2809 0.7946 -0.4701
-5.9931 -3.0019 4.9931 -0.3230 0.9726 0.0961
5.0011 -4.9954 -5.0013 0.3356 -0.5334 0.7261

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0158
_diffrn_reflns_av_unetI/netI     0.0207
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            4910
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.405
_diffrn_reflns_theta_min         4.492
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2850
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -56.00  34.00   0.50    0.50    --  -38.50  38.00  30.00  180
  2  ω    -68.00 -18.00   0.50    0.50    --  -38.50 -57.00  30.00  100
  3  ω   -105.00 -76.00   0.50    0.50    --  -38.50 -57.00  30.00   58
  4  ω   -107.00 -25.00   0.50    0.50    --  -38.50 -57.00-120.00  164
  5  ω     37.00 101.00   0.50    2.00    --  111.00 -30.00 150.00  128
  6  ω     71.00 103.00   0.50    2.00    --  111.00 -94.00  90.00   64
  7  ω     92.00 134.00   0.50    2.00    --  111.00 -45.00   0.00   84
  8  ω     88.00 175.00   0.50    2.00    --  111.00  30.00  30.00  174
  9  ω    133.00 160.00   0.50    2.00    --  111.00  30.00 -60.00   54
 10  ω     91.00 132.00   0.50    2.00    --  111.00  30.00 -60.00   82
 11  ω     90.00 172.00   0.50    2.00    --  111.00  45.00 -30.00  164
 12  ω    124.00 154.00   0.50    2.00    --  111.00 125.00 120.00   60
 13  ω     40.00  73.00   0.50    2.00    --  111.00 -45.00   0.00   66
 14  ω     61.00  93.00   0.50    2.00    --  111.00 -94.00  60.00   64
 15  ω     33.00  60.00   0.50    2.00    --  111.00 -94.00  90.00   54
 16  ω     98.00 140.00   0.50    2.00    --  111.00 -77.00-180.00   84
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.2312023000
_diffrn_orient_matrix_UB_12      -0.0304487000
_diffrn_orient_matrix_UB_13      0.1945068000
_diffrn_orient_matrix_UB_21      -0.1301213000
_diffrn_orient_matrix_UB_22      -0.0387878000
_diffrn_orient_matrix_UB_23      0.0152775000
_diffrn_orient_matrix_UB_31      -0.0196935000
_diffrn_orient_matrix_UB_32      -0.1002991000
_diffrn_orient_matrix_UB_33      -0.0646940000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1971
_reflns_number_total             2108
_reflns_odcompleteness_completeness 99.91
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_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 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_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         0.413
_refine_diff_density_min         -0.346
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     138
_refine_ls_number_reflns         2108
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0287
_refine_ls_R_factor_gt           0.0267
_refine_ls_restrained_S_all      1.071
_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)+(0.0367P)²+0.3592P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0701
_refine_ls_wR_factor_ref         0.0721
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C7(H7)
2.b Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C9(H9A,H9B,H9C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.04666(5) 0.61188(2) 0.28081(4) 0.01417(10) Uani 1 1 d . . . . .
F1 F 0.80676(14) 0.81558(6) 0.55063(11) 0.02556(19) Uani 1 1 d . . . . .
O1 O -0.12934(15) 0.68125(7) 0.20061(12) 0.0194(2) Uani 1 1 d . . . . .
O2 O -0.02166(16) 0.53236(7) 0.17166(12) 0.0201(2) Uani 1 1 d . . . . .
N1 N 0.17481(18) 0.56403(7) 0.46149(14) 0.0161(2) Uani 1 1 d . . . . .
N2 N 0.26689(18) 0.58384(8) 0.69343(14) 0.0162(2) Uani 1 1 d . . . . .
C1 C 0.2692(2) 0.67574(9) 0.35475(15) 0.0146(2) Uani 1 1 d . . . . .
C2 C 0.4342(2) 0.62218(9) 0.40406(17) 0.0174(2) Uani 1 1 d . . . . .
H2 H 0.4210 0.5550 0.3912 0.021 Uiso 1 1 calc R . . . .
C3 C 0.6184(2) 0.66947(10) 0.47249(17) 0.0190(3) Uani 1 1 d . . . . .
H3 H 0.7332 0.6350 0.5096 0.023 Uiso 1 1 calc R . . . .
C4 C 0.6261(2) 0.76961(10) 0.48390(16) 0.0182(3) Uani 1 1 d . . . . .
C5 C 0.4613(2) 0.82456(9) 0.43147(17) 0.0197(3) Uani 1 1 d . . . . .
H5 H 0.4709 0.8919 0.4388 0.024 Uiso 1 1 calc R . . . .
C6 C 0.2805(2) 0.77633(9) 0.36743(16) 0.0175(3) Uani 1 1 d . . . . .
H6 H 0.1682 0.8110 0.3334 0.021 Uiso 1 1 calc R . . . .
C7 C 0.1628(2) 0.61306(8) 0.54241(16) 0.0146(2) Uani 1 1 d . . . . .
H7 H 0.0779 0.6703 0.4910 0.018 Uiso 1 1 calc R . . . .
C8 C 0.4069(2) 0.49568(9) 0.78380(17) 0.0201(3) Uani 1 1 d . . . . .
H8A H 0.3423 0.4510 0.7930 0.030 Uiso 1 1 calc GR . . . .
H8B H 0.5617 0.5118 0.9011 0.030 Uiso 1 1 calc GR . . . .
H8C H 0.4087 0.4664 0.7166 0.030 Uiso 1 1 calc GR . . . .
C9 C 0.2525(2) 0.63853(9) 0.78223(17) 0.0193(3) Uani 1 1 d . . . . .
H9A H 0.1659 0.6970 0.7167 0.029 Uiso 1 1 calc GR . . . .
H9B H 0.4052 0.6547 0.9012 0.029 Uiso 1 1 calc GR . . . .
H9C H 0.1769 0.5998 0.7872 0.029 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O1 1.4488(9) . ?
S1 O2 1.4405(9) . ?
S1 N1 1.6220(11) . ?
S1 C1 1.7690(12) . ?
F1 C4 1.3585(15) . ?
N1 C7 1.3167(16) . ?
N2 C7 1.3144(16) . ?
N2 C8 1.4611(16) . ?
N2 C9 1.4604(16) . ?
C1 C2 1.3895(17) . ?
C1 C6 1.3895(17) . ?
C2 H2 0.9300 . ?
C2 C3 1.3859(18) . ?
C3 H3 0.9300 . ?
C3 C4 1.3832(19) . ?
C4 C5 1.3794(19) . ?
C5 H5 0.9300 . ?
C5 C6 1.3895(18) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 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 112.46(5) . . ?
O1 S1 C1 107.97(6) . . ?
O2 S1 O1 117.61(6) . . ?
O2 S1 N1 106.36(5) . . ?
O2 S1 C1 107.57(6) . . ?
N1 S1 C1 103.94(6) . . ?
C7 N1 S1 116.41(9) . . ?
C7 N2 C8 121.98(11) . . ?
C7 N2 C9 121.92(11) . . ?
C9 N2 C8 116.10(10) . . ?
C2 C1 S1 118.02(10) . . ?
C2 C1 C6 121.54(11) . . ?
C6 C1 S1 120.41(10) . . ?
C1 C2 H2 120.2 . . ?
C3 C2 C1 119.55(12) . . ?
C3 C2 H2 120.2 . . ?
C2 C3 H3 121.1 . . ?
C4 C3 C2 117.88(12) . . ?
C4 C3 H3 121.1 . . ?
F1 C4 C3 117.62(12) . . ?
F1 C4 C5 118.75(12) . . ?
C5 C4 C3 123.64(12) . . ?
C4 C5 H5 121.0 . . ?
C4 C5 C6 118.06(12) . . ?
C6 C5 H5 121.0 . . ?
C1 C6 C5 119.29(12) . . ?
C1 C6 H6 120.4 . . ?
C5 C6 H6 120.4 . . ?
N1 C7 H7 118.9 . . ?
N2 C7 N1 122.23(11) . . ?
N2 C7 H7 118.9 . . ?
N2 C8 H8A 109.5 . . ?
N2 C8 H8B 109.5 . . ?
N2 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N2 C9 H9A 109.5 . . ?
N2 C9 H9B 109.5 . . ?
N2 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.419
_oxdiff_exptl_absorpt_empirical_full_min 0.830
####################################################################### 
# 
# 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_16
_database_code_depnum_ccdc_archive 'CCDC 2051048'
loop_
_audit_author_name
_audit_author_address
'Felix Hennersdorf'
;TU Dresden
Germany
;
_audit_update_record             
;
2020-12-17 deposited with the CCDC.	2021-04-01 downloaded from the CCDC.
;
_audit_creation_date             2017-09-22
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H14 N2 O2 S'
_chemical_formula_sum            'C14 H14 N2 O2 S'
_chemical_formula_weight         274.33
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C60 H60 N4 O8 S4 '
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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                   10.77093(12)
_cell_length_b                   11.69446(14)
_cell_length_c                   10.46614(12)
_cell_angle_alpha                90
_cell_angle_beta                 91.3982(10)
_cell_angle_gamma                90
_cell_volume                     1317.92(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4888
_cell_measurement_temperature    99.99(10)
_cell_measurement_theta_max      76.3040
_cell_measurement_theta_min      5.5720
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.183
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.95833
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.383
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             576
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-5 5 0 0.0395
1 -6 4 0.0556
-1 6 -4 0.0652
5 1 -5 0.0973
4 2 5 0.0450
0 7 2 0.0395
-4 4 -3 0.0575
-1 -7 -2 0.0371
-4 -4 -5 0.0650
-2 7 -1 0.0463
1 7 3 0.0364
7 1 1 0.0499
5 6 0 0.0495
2 7 -1 0.0510
-7 1 -1 0.0580
-1 -7 1 0.0490
2 -7 -2 0.0385
-2 -2 -6 0.0681

_exptl_crystal_size_max          0.211
_exptl_crystal_size_mid          0.117
_exptl_crystal_size_min          0.078
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-4.9967 5.0043 -0.0033 -0.3183 0.2262 0.8904
1.0001 -6.0005 4.0000 -0.3942 0.1818 -0.8984
-1.0001 6.0005 -4.0000 0.3942 -0.1818 0.8984
4.9958 0.9952 -4.9959 0.8952 -0.4921 -0.0174
3.9959 1.9941 5.0019 -0.5374 -0.7712 -0.2758
-0.0014 6.9979 1.9997 -0.3993 -0.5644 0.6767
-3.9972 4.0041 -3.0022 0.1560 0.2782 0.8433
-0.9977 -6.9968 -2.0004 0.3536 0.6809 -0.6077
-3.9956 -3.9936 -5.0019 0.5733 0.9139 0.0575
-1.9996 7.0007 -1.0012 -0.0801 -0.2339 0.9455
0.9977 6.9966 3.0002 -0.4905 -0.7134 0.5641
6.9938 0.9918 1.0045 0.1653 -0.9199 -0.4171
4.9946 5.9930 0.0034 0.1210 -1.0111 0.3101
1.9970 6.9963 -0.9985 0.1028 -0.7002 0.6697
-6.9942 1.0077 -1.0045 -0.2012 0.7772 0.6354
-0.9979 -6.9974 0.9992 -0.0571 0.5837 -0.7387
1.9997 -7.0001 -1.9983 0.4908 0.3312 -0.8146
-1.9976 -1.9961 -6.0004 0.7657 0.5705 0.1815

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0170
_diffrn_reflns_av_unetI/netI     0.0202
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            6774
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.537
_diffrn_reflns_theta_min         4.106
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2850
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -22.00  64.00   0.50    0.80    --   42.62 -38.00  90.00  172
  2  ω      1.00  69.00   0.50    0.80    --   42.62 -99.00   0.00  136
  3  ω      1.00  49.00   0.50    0.80    --   42.62 -99.00  90.00   96
  4  ω     70.00 106.00   0.50    3.20    --  111.00 -94.00  90.00   72
  5  ω     77.00 102.00   0.50    3.20    --  111.00 -94.00  60.00   50
  6  ω     40.00  87.00   0.50    3.20    --  111.00-125.00 -60.00   94
  7  ω     51.00  93.00   0.50    3.20    --  111.00-125.00-180.00   84
  8  ω     46.00  98.00   0.50    3.20    --  111.00 -45.00 -90.00  104
  9  ω    132.00 176.00   0.50    3.20    --  111.00  30.00 -30.00   88
 10  ω     97.00 123.00   0.50    3.20    --  111.00  30.00 -30.00   52
 11  ω     89.00 149.00   0.50    3.20    --  111.00  45.00  30.00  120
 12  ω     87.00 161.00   0.50    3.20    --  111.00  45.00 120.00  148
 13  ω     30.00  86.00   0.50    3.20    --  111.00 -94.00 -60.00  112
 14  ω     36.00  64.00   0.50    3.20    --  111.00 -94.00  60.00   56
 15  ω     47.00  95.00   0.50    0.80    --   42.62-125.00-150.00   96
 16  ω     89.00 175.00   0.50    3.20    --  111.00  77.00-150.00  172
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0458423000
_diffrn_orient_matrix_UB_12      -0.0179311000
_diffrn_orient_matrix_UB_13      -0.1369119000
_diffrn_orient_matrix_UB_21      -0.1167438000
_diffrn_orient_matrix_UB_22      -0.0713959000
_diffrn_orient_matrix_UB_23      -0.0324581000
_diffrn_orient_matrix_UB_31      -0.0688568000
_diffrn_orient_matrix_UB_32      0.1091537000
_diffrn_orient_matrix_UB_33      -0.0436389000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2622
_reflns_number_total             2729
_reflns_odcompleteness_completeness 99.89
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_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 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_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         0.336
_refine_diff_density_min         -0.424
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2729
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0295
_refine_ls_R_factor_gt           0.0284
_refine_ls_restrained_S_all      1.048
_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)+(0.0372P)²+0.5257P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0740
_refine_ls_wR_factor_ref         0.0750
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C7(H7), C10(H10), C11(H11), C12(H12),
 C13(H13), C14(H14)
2.b Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.26873(2) 0.67292(2) 0.89651(3) 0.01583(10) Uani 1 1 d . . . . .
O1 O 0.26118(8) 0.63582(8) 1.02741(8) 0.02155(19) Uani 1 1 d . . . . .
O2 O 0.27231(8) 0.79457(7) 0.87235(9) 0.0220(2) Uani 1 1 d . . . . .
N1 N 0.38621(9) 0.60557(8) 0.83710(9) 0.0177(2) Uani 1 1 d . . . . .
N2 N 0.54119(9) 0.60525(8) 0.69090(9) 0.0158(2) Uani 1 1 d . . . . .
C1 C 0.14011(10) 0.61610(10) 0.80995(11) 0.0168(2) Uani 1 1 d . . . . .
C2 C 0.10818(12) 0.66292(11) 0.69140(12) 0.0217(3) Uani 1 1 d . . . . .
H2 H 0.1525 0.7244 0.6594 0.026 Uiso 1 1 calc R . . . .
C3 C 0.00921(12) 0.61652(12) 0.62154(13) 0.0269(3) Uani 1 1 d . . . . .
H3 H -0.0136 0.6474 0.5425 0.032 Uiso 1 1 calc R . . . .
C4 C -0.05579(12) 0.52395(12) 0.66948(13) 0.0274(3) Uani 1 1 d . . . . .
H4 H -0.1215 0.4926 0.6219 0.033 Uiso 1 1 calc R . . . .
C5 C -0.02336(12) 0.47806(12) 0.78757(13) 0.0266(3) Uani 1 1 d . . . . .
H5 H -0.0677 0.4165 0.8194 0.032 Uiso 1 1 calc R . . . .
C6 C 0.07554(11) 0.52386(11) 0.85884(12) 0.0210(2) Uani 1 1 d . . . . .
H6 H 0.0980 0.4931 0.9380 0.025 Uiso 1 1 calc R . . . .
C7 C 0.44330(10) 0.65525(10) 0.74326(11) 0.0156(2) Uani 1 1 d . . . . .
H7 H 0.4156 0.7257 0.7129 0.019 Uiso 1 1 calc R . . . .
C8 C 0.58365(11) 0.49397(10) 0.73976(12) 0.0191(2) Uani 1 1 d . . . . .
H8A H 0.5455 0.4340 0.6900 0.029 Uiso 1 1 calc GR . . . .
H8B H 0.5610 0.4862 0.8275 0.029 Uiso 1 1 calc GR . . . .
H8C H 0.6723 0.4890 0.7337 0.029 Uiso 1 1 calc GR . . . .
C9 C 0.60677(10) 0.65669(10) 0.58835(11) 0.0156(2) Uani 1 1 d . . . . .
C10 C 0.62229(11) 0.77476(10) 0.58180(11) 0.0181(2) Uani 1 1 d . . . . .
H10 H 0.5873 0.8219 0.6428 0.022 Uiso 1 1 calc R . . . .
C11 C 0.69033(11) 0.82175(11) 0.48368(12) 0.0209(2) Uani 1 1 d . . . . .
H11 H 0.6996 0.9007 0.4785 0.025 Uiso 1 1 calc R . . . .
C12 C 0.74450(12) 0.75204(12) 0.39339(11) 0.0225(3) Uani 1 1 d . . . . .
H12 H 0.7910 0.7839 0.3287 0.027 Uiso 1 1 calc R . . . .
C13 C 0.72881(11) 0.63437(12) 0.40034(11) 0.0223(3) Uani 1 1 d . . . . .
H13 H 0.7646 0.5874 0.3397 0.027 Uiso 1 1 calc R . . . .
C14 C 0.66001(11) 0.58612(10) 0.49732(11) 0.0193(2) Uani 1 1 d . . . . .
H14 H 0.6496 0.5073 0.5014 0.023 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 1.4413(9) . ?
S1 O2 1.4455(9) . ?
S1 N1 1.6268(10) . ?
S1 C1 1.7664(12) . ?
N1 C7 1.3075(15) . ?
N2 C7 1.3349(15) . ?
N2 C8 1.4673(14) . ?
N2 C9 1.4317(14) . ?
C1 C2 1.3916(17) . ?
C1 C6 1.3880(17) . ?
C2 H2 0.9300 . ?
C2 C3 1.3883(19) . ?
C3 H3 0.9300 . ?
C3 C4 1.390(2) . ?
C4 H4 0.9300 . ?
C4 C5 1.384(2) . ?
C5 H5 0.9300 . ?
C5 C6 1.3926(18) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 C10 1.3928(17) . ?
C9 C14 1.3944(16) . ?
C10 H10 0.9300 . ?
C10 C11 1.3894(17) . ?
C11 H11 0.9300 . ?
C11 C12 1.3874(18) . ?
C12 H12 0.9300 . ?
C12 C13 1.3886(19) . ?
C13 H13 0.9300 . ?
C13 C14 1.3908(17) . ?
C14 H14 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 O2 117.70(5) . . ?
O1 S1 N1 106.26(5) . . ?
O1 S1 C1 108.21(5) . . ?
O2 S1 N1 112.66(5) . . ?
O2 S1 C1 107.72(6) . . ?
N1 S1 C1 103.26(5) . . ?
C7 N1 S1 117.15(8) . . ?
C7 N2 C8 119.21(10) . . ?
C7 N2 C9 122.20(10) . . ?
C9 N2 C8 118.59(9) . . ?
C2 C1 S1 118.88(9) . . ?
C6 C1 S1 119.81(9) . . ?
C6 C1 C2 121.28(11) . . ?
C1 C2 H2 120.5 . . ?
C3 C2 C1 119.06(12) . . ?
C3 C2 H2 120.5 . . ?
C2 C3 H3 120.0 . . ?
C2 C3 C4 120.10(12) . . ?
C4 C3 H3 120.0 . . ?
C3 C4 H4 119.8 . . ?
C5 C4 C3 120.40(12) . . ?
C5 C4 H4 119.8 . . ?
C4 C5 H5 119.9 . . ?
C4 C5 C6 120.14(12) . . ?
C6 C5 H5 119.9 . . ?
C1 C6 C5 119.02(12) . . ?
C1 C6 H6 120.5 . . ?
C5 C6 H6 120.5 . . ?
N1 C7 N2 120.29(11) . . ?
N1 C7 H7 119.9 . . ?
N2 C7 H7 119.9 . . ?
N2 C8 H8A 109.5 . . ?
N2 C8 H8B 109.5 . . ?
N2 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C10 C9 N2 121.02(10) . . ?
C10 C9 C14 120.08(11) . . ?
C14 C9 N2 118.84(11) . . ?
C9 C10 H10 120.2 . . ?
C11 C10 C9 119.64(11) . . ?
C11 C10 H10 120.2 . . ?
C10 C11 H11 119.7 . . ?
C12 C11 C10 120.62(11) . . ?
C12 C11 H11 119.7 . . ?
C11 C12 H12 120.2 . . ?
C11 C12 C13 119.53(11) . . ?
C13 C12 H12 120.2 . . ?
C12 C13 H13 119.7 . . ?
C12 C13 C14 120.53(11) . . ?
C14 C13 H13 119.7 . . ?
C9 C14 H14 120.2 . . ?
C13 C14 C9 119.59(11) . . ?
C13 C14 H14 120.2 . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.085
_oxdiff_exptl_absorpt_empirical_full_min 0.921
####################################################################### 
# 
# 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_24f
_database_code_depnum_ccdc_archive 'CCDC 2051055'
loop_
_audit_author_name
_audit_author_address
'Felix Hennersdorf'
;TU Dresden
Germany
;
_audit_update_record             
;
2020-12-17 deposited with the CCDC.	2021-04-01 downloaded from the CCDC.
;
_audit_creation_date             2018-04-19
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H10.01 F0.99 N O4 S2, H2 O'
_chemical_formula_sum            'C12 H12.01 F0.99 N O5 S2'
_chemical_formula_weight         333.21
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C96 F32 N8 O24 S16 H1 '
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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                   13.2220(3)
_cell_length_b                   13.3607(3)
_cell_length_c                   16.1071(4)
_cell_angle_alpha                90
_cell_angle_beta                 103.931(2)
_cell_angle_gamma                90
_cell_volume                     2761.72(11)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    10311
_cell_measurement_temperature    100.5(8)
_cell_measurement_theta_max      76.7140
_cell_measurement_theta_min      3.3010
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    3.828
_exptl_absorpt_correction_T_max  0.792
_exptl_absorpt_correction_T_min  0.527
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.603
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1376
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
9 1 -3 0.0998
0 9 -1 0.0834
-9 -1 3 0.0708
5 -7 -1 0.0973
0 -9 1 0.1229
1 0 10 0.0396
-1 0 -10 0.0217
0 7 6 0.0830
0 1 10 0.0432
3 2 -10 0.0660

_exptl_crystal_size_max          0.219
_exptl_crystal_size_mid          0.171
_exptl_crystal_size_min          0.061
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
8.9862 1.0246 -3.0196 0.3622 -0.3122 0.9394
-0.0105 9.0052 -0.9995 -0.6147 0.6149 0.5763
-8.9862 -1.0246 3.0196 -0.3622 0.3122 -0.9394
5.0011 -6.9908 -1.0111 0.7282 -0.6767 0.0389
0.0105 -9.0052 0.9995 0.6147 -0.6149 -0.5763
1.0024 0.0093 9.9862 -0.6066 -0.8190 0.0503
-1.0024 -0.0093 -9.9862 0.6066 0.8190 -0.0503
-0.0057 7.0084 5.9927 -0.9078 -0.0318 0.4173
0.0025 1.0071 9.9887 -0.7094 -0.6926 0.0180
2.9902 2.0035 -9.9965 0.5658 0.6732 0.4600

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0251
_diffrn_reflns_av_unetI/netI     0.0265
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            16013
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.652
_diffrn_reflns_theta_min         3.895
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.5(8)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2850
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -60.00  34.00   0.50    0.50    --  -38.50  38.00  90.00  188
  2  ω     24.00  50.00   0.50    0.50    --   42.62-125.00 -90.00   52
  3  ω     40.00 133.00   0.50    2.00    --  111.00 -30.00 -90.00  186
  4  ω     92.00 178.00   0.50    2.00    --  111.00  30.00-180.00  172
  5  ω    149.00 176.00   0.50    2.00    --  111.00 125.00 -60.00   54
  6  ω     98.00 132.00   0.50    2.00    --  111.00 125.00 -60.00   68
  7  ω     94.00 149.00   0.50    2.00    --  111.00 125.00   0.00  110
  8  ω     88.00 121.00   0.50    2.00    --  111.00  30.00 120.00   66
  9  ω    146.00 172.00   0.50    2.00    --  111.00  30.00 120.00   52
 10  ω     80.00 157.00   0.50    2.00    --  111.00  77.00 120.00  154
 11  ω     69.00 139.00   0.50    2.00    --  111.00 -61.00 -90.00  140
 12  ω     55.00 121.00   0.50    2.00    --  111.00-125.00 -30.00  132
 13  ω     50.00 110.00   0.50    2.00    --  111.00-125.00 -90.00  120
 14  ω     45.00  72.00   0.50    2.00    --  111.00 -94.00 -90.00   54
 15  ω     34.00  76.00   0.50    2.00    --  111.00 -94.00-150.00   84
 16  ω   -101.00 -74.00   0.50    0.50    --  -38.50-141.00  21.00   54
 17  ω   -102.00 -17.00   0.50    0.50    --  -38.50 -38.00 -90.00  170
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0275667000
_diffrn_orient_matrix_UB_12      -0.0752674000
_diffrn_orient_matrix_UB_13      -0.0634370000
_diffrn_orient_matrix_UB_21      -0.0668831000
_diffrn_orient_matrix_UB_22      0.0598435000
_diffrn_orient_matrix_UB_23      -0.0753534000
_diffrn_orient_matrix_UB_31      0.0957251000
_diffrn_orient_matrix_UB_32      0.0635902000
_diffrn_orient_matrix_UB_33      -0.0046356000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5473
_reflns_number_total             5763
_reflns_odcompleteness_completeness 99.83
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_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 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_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         0.806
_refine_diff_density_min         -0.870
_refine_diff_density_rms         0.118
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.136
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     427
_refine_ls_number_reflns         5763
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0646
_refine_ls_R_factor_gt           0.0629
_refine_ls_restrained_S_all      1.136
_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)+(0.0223P)²+20.4859P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1669
_refine_ls_wR_factor_ref         0.1676
_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 O(H,H) groups
2. Others
 1*[Sof(F1D)+Sof(H3D)]+1*[Sof(F1F)+Sof(H11D)]+1*[Sof(F1E)+Sof(H9D)]=1 with esd
 of 0.01
 1*[Sof(F1B)+Sof(H3A)]+1*[Sof(F2B)+Sof(H5A)]+1*[Sof(F1A)+Sof(H9A)]=1 with esd
 of 0.01
 Sof(H3D)=1-FVAR(1)
 Sof(F1D)=FVAR(1)
 Sof(H11D)=1-FVAR(2)
 Sof(F1F)=FVAR(2)
 Sof(H9D)=1-FVAR(3)
 Sof(F1E)=FVAR(3)
 Sof(H3A)=1-FVAR(4)
 Sof(F1B)=FVAR(4)
 Sof(H5A)=1-FVAR(5)
 Sof(F2B)=FVAR(5)
 Sof(H9A)=1-FVAR(6)
 Sof(F1A)=FVAR(6)
3.a Riding coordinates:
 N1A(H1A), N1D(H1D)
3.b Free rotating group:
 O5A(H5AA,H5AB), O5D(H5DA,H5DB)
3.c Aromatic/amide H refined with riding coordinates:
 C2A(H2A), C3A(H3A), C4A(H4A), C5A(H5A), C6A(H6A), C8A(H8A), C9A(H9A),
 C10A(H10A), C11A(H11A), C12A(H12A), C2D(H2D), C3D(H3D), C4D(H4D), C5D(H5D),
 C6D(H6D), C8D(H8D), C9D(H9D), C10D(H10D), C11D(H11D), C12D(H12D)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1A S 0.15425(8) 0.67135(7) 0.71981(6) 0.0158(2) Uani 1 1 d . . . . .
S2A S 0.36434(8) 0.57929(7) 0.75633(6) 0.0162(2) Uani 1 1 d . . . . .
F1A F 0.3615(6) 0.3738(5) 0.4941(4) 0.030(2) Uani 0.399(10) 1 d . . P A 1
F1B F 0.1364(5) 0.8945(4) 0.4657(4) 0.031(2) Uani 0.458(10) 1 d . . P B 2
F2B F 0.079(2) 0.5487(19) 0.4148(17) 0.047(9) Uani 0.132(11) 1 d . . P C 3
O1A O 0.1205(2) 0.7577(2) 0.75780(19) 0.0214(6) Uani 1 1 d . . . . .
O2A O 0.1162(2) 0.5738(2) 0.73245(19) 0.0207(6) Uani 1 1 d . . . . .
O3A O 0.4625(2) 0.6191(2) 0.80291(19) 0.0217(6) Uani 1 1 d . . . . .
O4A O 0.3252(2) 0.4899(2) 0.78559(19) 0.0212(6) Uani 1 1 d . . . . .
N1A N 0.2823(3) 0.6712(3) 0.7593(2) 0.0158(7) Uani 1 1 d . . . . .
H1A H 0.3072 0.7250 0.7426 0.019 Uiso 1 1 d R . . . .
C1A C 0.1358(3) 0.6917(3) 0.6092(3) 0.0165(8) Uani 1 1 d . . . . .
C2A C 0.1441(3) 0.7889(3) 0.5808(3) 0.0198(8) Uani 1 1 d . . . . .
H2A H 0.1572 0.8426 0.6185 0.024 Uiso 1 1 calc R . . . .
C3A C 0.1321(3) 0.8021(3) 0.4935(3) 0.0224(9) Uani 1 1 d . . . . .
H3A H 0.1362 0.8665 0.4725 0.027 Uiso 0.542(10) 1 calc R . P B 1
C4A C 0.1143(3) 0.7232(4) 0.4370(3) 0.0224(9) Uani 1 1 d . . . . .
H4A H 0.1069 0.7343 0.3788 0.027 Uiso 1 1 calc R . . . .
C5A C 0.1073(3) 0.6268(4) 0.4676(3) 0.0227(9) Uani 1 1 d . . . . .
H5A H 0.0958 0.5732 0.4297 0.027 Uiso 0.868(11) 1 calc R . P C 4
C6A C 0.1175(3) 0.6101(3) 0.5542(3) 0.0187(8) Uani 1 1 d . . . . .
H6A H 0.1122 0.5458 0.5749 0.022 Uiso 1 1 calc R . . . .
C7A C 0.3681(3) 0.5639(3) 0.6487(3) 0.0172(8) Uani 1 1 d . . . . .
C8A C 0.3557(3) 0.4684(3) 0.6138(3) 0.0201(8) Uani 1 1 d . . . . .
H8A H 0.3441 0.4133 0.6455 0.024 Uiso 1 1 calc R . . . .
C9A C 0.3616(4) 0.4591(4) 0.5292(3) 0.0248(10) Uani 1 1 d . . . . .
H9A H 0.3547 0.3960 0.5042 0.030 Uiso 0.601(10) 1 calc R . P A 2
C10A C 0.3773(4) 0.5406(4) 0.4812(3) 0.0271(10) Uani 1 1 d . . . . .
H10A H 0.3799 0.5322 0.4244 0.033 Uiso 1 1 calc R . . . .
C11A C 0.3890(4) 0.6352(4) 0.5180(3) 0.0256(10) Uani 1 1 d . . . . .
H11A H 0.3991 0.6903 0.4856 0.031 Uiso 1 1 calc R . . . .
C12A C 0.3858(3) 0.6478(3) 0.6023(3) 0.0216(9) Uani 1 1 d . . . . .
H12A H 0.3952 0.7107 0.6277 0.026 Uiso 1 1 calc R . . . .
S1D S 0.65165(8) 0.91350(7) 0.72294(6) 0.0154(2) Uani 1 1 d . . . . .
S2D S 0.86504(7) 0.82804(7) 0.75894(6) 0.0152(2) Uani 1 1 d . . . . .
F1D F 0.6385(5) 1.1203(5) 0.4577(4) 0.034(2) Uani 0.464(10) 1 d . . P D 1
F1E F 0.8650(6) 0.6011(5) 0.5098(5) 0.029(2) Uani 0.401(10) 1 d . . P E 2
F1F F 0.9034(18) 0.9446(17) 0.4724(12) 0.030(7) Uani 0.131(10) 1 d . . P F 3
O1D O 0.6897(2) 1.0049(2) 0.76511(19) 0.0217(6) Uani 1 1 d . . . . .
O2D O 0.5575(2) 0.8705(2) 0.7365(2) 0.0219(6) Uani 1 1 d . . . . .
O3D O 0.9058(2) 0.7452(2) 0.81234(19) 0.0213(6) Uani 1 1 d . . . . .
O4D O 0.9000(2) 0.9278(2) 0.78101(19) 0.0211(6) Uani 1 1 d . . . . .
N1D N 0.7379(3) 0.8247(3) 0.7559(2) 0.0164(7) Uani 1 1 d . . . . .
H1D H 0.7128 0.7696 0.7319 0.020 Uiso 1 1 d R . . . .
C1D C 0.6387(3) 0.9281(3) 0.6124(3) 0.0166(8) Uani 1 1 d . . . . .
C2D C 0.6499(3) 1.0228(3) 0.5803(3) 0.0205(9) Uani 1 1 d . . . . .
H2D H 0.6666 1.0780 0.6162 0.025 Uiso 1 1 calc R . . . .
C3D C 0.6350(4) 1.0314(4) 0.4925(3) 0.0276(10) Uani 1 1 d . . . . .
H3D H 0.6405 1.0943 0.4692 0.033 Uiso 0.536(10) 1 calc R . P D 2
C4D C 0.6124(4) 0.9502(4) 0.4386(3) 0.0271(10) Uani 1 1 d . . . . .
H4D H 0.6039 0.9581 0.3800 0.033 Uiso 1 1 calc R . . . .
C5D C 0.6024(4) 0.8561(4) 0.4727(3) 0.0251(10) Uani 1 1 d . . . . .
H5D H 0.5873 0.8008 0.4368 0.030 Uiso 1 1 calc R . . . .
C6D C 0.6149(3) 0.8446(3) 0.5600(3) 0.0207(9) Uani 1 1 d . . . . .
H6D H 0.6075 0.7820 0.5831 0.025 Uiso 1 1 calc R . . . .
C7D C 0.8740(3) 0.8049(3) 0.6535(3) 0.0157(8) Uani 1 1 d . . . . .
C8D C 0.8651(3) 0.7067(3) 0.6241(3) 0.0194(8) Uani 1 1 d . . . . .
H8D H 0.8582 0.6536 0.6597 0.023 Uiso 1 1 calc R . . . .
C9D C 0.8670(3) 0.6915(4) 0.5392(3) 0.0231(9) Uani 1 1 d . . . . .
H9D H 0.8621 0.6264 0.5180 0.028 Uiso 0.599(10) 1 calc R . P E 1
C10D C 0.8759(3) 0.7692(4) 0.4855(3) 0.0249(10) Uani 1 1 d . . . . .
H10D H 0.8756 0.7569 0.4286 0.030 Uiso 1 1 calc R . . . .
C11D C 0.8854(4) 0.8662(4) 0.5172(3) 0.0249(10) Uani 1 1 d . . . . .
H11D H 0.8917 0.9191 0.4812 0.030 Uiso 0.869(10) 1 calc R . P F 4
C12D C 0.8855(3) 0.8852(3) 0.6017(3) 0.0191(8) Uani 1 1 d . . . . .
H12D H 0.8930 0.9501 0.6233 0.023 Uiso 1 1 calc R . . . .
O5A O 0.3597(3) 0.8576(3) 0.7760(3) 0.0381(9) Uani 1 1 d . . . . .
H5AA H 0.4168 0.8655 0.7614 0.057 Uiso 1 1 d G . . . .
H5AB H 0.3147 0.8985 0.7485 0.057 Uiso 1 1 d G . . . .
O5D O 0.6452(3) 0.6447(3) 0.7332(3) 0.0354(9) Uani 1 1 d . . . . .
H5DA H 0.5912 0.6380 0.7525 0.053 Uiso 1 1 d G . . . .
H5DB H 0.6774 0.5892 0.7368 0.053 Uiso 1 1 d G . . . .


_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
S1A O1A 1.427(3) . ?
S1A O2A 1.430(3) . ?
S1A N1A 1.660(4) . ?
S1A C1A 1.760(4) . ?
S2A O3A 1.436(3) . ?
S2A O4A 1.427(3) . ?
S2A N1A 1.647(3) . ?
S2A C7A 1.759(4) . ?
F1A C9A 1.272(8) . ?
F1B C3A 1.319(7) . ?
F2B C5A 1.34(3) . ?
N1A H1A 0.8599 . ?
C1A C2A 1.390(6) . ?
C1A C6A 1.389(6) . ?
C2A H2A 0.9300 . ?
C2A C3A 1.387(6) . ?
C3A H3A 0.9300 . ?
C3A C4A 1.376(6) . ?
C4A H4A 0.9300 . ?
C4A C5A 1.390(7) . ?
C5A H5A 0.9300 . ?
C5A C6A 1.387(6) . ?
C6A H6A 0.9300 . ?
C7A C8A 1.388(6) . ?
C7A C12A 1.397(6) . ?
C8A H8A 0.9300 . ?
C8A C9A 1.388(6) . ?
C9A H9A 0.9300 . ?
C9A C10A 1.381(7) . ?
C10A H10A 0.9300 . ?
C10A C11A 1.388(7) . ?
C11A H11A 0.9300 . ?
C11A C12A 1.380(6) . ?
C12A H12A 0.9300 . ?
S1D O1D 1.428(3) . ?
S1D O2D 1.434(3) . ?
S1D N1D 1.642(4) . ?
S1D C1D 1.759(4) . ?
S2D O3D 1.426(3) . ?
S2D O4D 1.428(3) . ?
S2D N1D 1.671(4) . ?
S2D C7D 1.758(4) . ?
F1D C3D 1.319(8) . ?
F1E C9D 1.295(8) . ?
F1F C11D 1.33(2) . ?
N1D H1D 0.8601 . ?
C1D C2D 1.388(6) . ?
C1D C6D 1.389(6) . ?
C2D H2D 0.9300 . ?
C2D C3D 1.385(6) . ?
C3D H3D 0.9300 . ?
C3D C4D 1.377(7) . ?
C4D H4D 0.9300 . ?
C4D C5D 1.391(7) . ?
C5D H5D 0.9300 . ?
C5D C6D 1.383(6) . ?
C6D H6D 0.9300 . ?
C7D C8D 1.390(6) . ?
C7D C12D 1.389(6) . ?
C8D H8D 0.9300 . ?
C8D C9D 1.388(6) . ?
C9D H9D 0.9300 . ?
C9D C10D 1.375(7) . ?
C10D H10D 0.9300 . ?
C10D C11D 1.387(7) . ?
C11D H11D 0.9300 . ?
C11D C12D 1.385(6) . ?
C12D H12D 0.9300 . ?
O5A H5AA 0.8493 . ?
O5A H5AB 0.8493 . ?
O5D H5DA 0.8493 . ?
O5D H5DB 0.8498 . ?

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
O1A S1A O2A 121.30(19) . . ?
O1A S1A N1A 103.39(18) . . ?
O1A S1A C1A 109.12(19) . . ?
O2A S1A N1A 107.82(18) . . ?
O2A S1A C1A 108.49(19) . . ?
N1A S1A C1A 105.57(18) . . ?
O3A S2A N1A 103.14(18) . . ?
O3A S2A C7A 108.77(19) . . ?
O4A S2A O3A 119.46(19) . . ?
O4A S2A N1A 108.74(18) . . ?
O4A S2A C7A 109.1(2) . . ?
N1A S2A C7A 106.92(19) . . ?
S1A N1A H1A 108.1 . . ?
S2A N1A S1A 127.4(2) . . ?
S2A N1A H1A 108.1 . . ?
C2A C1A S1A 118.4(3) . . ?
C6A C1A S1A 119.0(3) . . ?
C6A C1A C2A 122.6(4) . . ?
C1A C2A H2A 121.5 . . ?
C3A C2A C1A 117.0(4) . . ?
C3A C2A H2A 121.5 . . ?
F1B C3A C2A 117.4(5) . . ?
F1B C3A C4A 120.5(5) . . ?
C2A C3A H3A 118.9 . . ?
C4A C3A C2A 122.1(4) . . ?
C4A C3A H3A 118.9 . . ?
C3A C4A H4A 120.3 . . ?
C3A C4A C5A 119.4(4) . . ?
C5A C4A H4A 120.3 . . ?
F2B C5A C4A 121.9(12) . . ?
F2B C5A C6A 117.1(12) . . ?
C4A C5A H5A 119.7 . . ?
C6A C5A C4A 120.5(4) . . ?
C6A C5A H5A 119.7 . . ?
C1A C6A H6A 120.8 . . ?
C5A C6A C1A 118.3(4) . . ?
C5A C6A H6A 120.8 . . ?
C8A C7A S2A 118.5(3) . . ?
C8A C7A C12A 122.7(4) . . ?
C12A C7A S2A 118.8(3) . . ?
C7A C8A H8A 121.6 . . ?
C9A C8A C7A 116.8(4) . . ?
C9A C8A H8A 121.6 . . ?
F1A C9A C8A 121.5(5) . . ?
F1A C9A C10A 116.2(5) . . ?
C8A C9A H9A 119.0 . . ?
C10A C9A C8A 122.1(4) . . ?
C10A C9A H9A 119.0 . . ?
C9A C10A H10A 120.2 . . ?
C9A C10A C11A 119.7(4) . . ?
C11A C10A H10A 120.2 . . ?
C10A C11A H11A 119.8 . . ?
C12A C11A C10A 120.3(4) . . ?
C12A C11A H11A 119.8 . . ?
C7A C12A H12A 120.8 . . ?
C11A C12A C7A 118.5(4) . . ?
C11A C12A H12A 120.8 . . ?
O1D S1D O2D 119.30(19) . . ?
O1D S1D N1D 109.02(19) . . ?
O1D S1D C1D 108.9(2) . . ?
O2D S1D N1D 102.81(18) . . ?
O2D S1D C1D 108.80(19) . . ?
N1D S1D C1D 107.35(18) . . ?
O3D S2D O4D 121.48(19) . . ?
O3D S2D N1D 103.23(18) . . ?
O3D S2D C7D 110.02(19) . . ?
O4D S2D N1D 107.20(18) . . ?
O4D S2D C7D 108.15(19) . . ?
N1D S2D C7D 105.57(18) . . ?
S1D N1D S2D 127.3(2) . . ?
S1D N1D H1D 108.1 . . ?
S2D N1D H1D 108.2 . . ?
C2D C1D S1D 119.0(3) . . ?
C2D C1D C6D 122.4(4) . . ?
C6D C1D S1D 118.6(3) . . ?
C1D C2D H2D 121.5 . . ?
C3D C2D C1D 117.0(4) . . ?
C3D C2D H2D 121.5 . . ?
F1D C3D C2D 119.9(5) . . ?
F1D C3D C4D 117.8(5) . . ?
C2D C3D H3D 118.9 . . ?
C4D C3D C2D 122.3(4) . . ?
C4D C3D H3D 118.9 . . ?
C3D C4D H4D 120.3 . . ?
C3D C4D C5D 119.4(4) . . ?
C5D C4D H4D 120.3 . . ?
C4D C5D H5D 119.9 . . ?
C6D C5D C4D 120.1(4) . . ?
C6D C5D H5D 119.9 . . ?
C1D C6D H6D 120.6 . . ?
C5D C6D C1D 118.8(4) . . ?
C5D C6D H6D 120.6 . . ?
C8D C7D S2D 118.4(3) . . ?
C12D C7D S2D 119.1(3) . . ?
C12D C7D C8D 122.5(4) . . ?
C7D C8D H8D 121.5 . . ?
C9D C8D C7D 117.0(4) . . ?
C9D C8D H8D 121.5 . . ?
F1E C9D C8D 119.6(5) . . ?
F1E C9D C10D 118.1(5) . . ?
C8D C9D H9D 118.9 . . ?
C10D C9D C8D 122.2(4) . . ?
C10D C9D H9D 118.9 . . ?
C9D C10D H10D 120.4 . . ?
C9D C10D C11D 119.2(4) . . ?
C11D C10D H10D 120.4 . . ?
F1F C11D C10D 123.4(10) . . ?
F1F C11D C12D 115.6(10) . . ?
C10D C11D H11D 119.6 . . ?
C12D C11D C10D 120.8(4) . . ?
C12D C11D H11D 119.6 . . ?
C7D C12D H12D 120.8 . . ?
C11D C12D C7D 118.3(4) . . ?
C11D C12D H12D 120.8 . . ?
H5AA O5A H5AB 109.6 . . ?
H5DA O5D H5DB 109.6 . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.246
_oxdiff_exptl_absorpt_empirical_full_min 0.837
####################################################################### 
# 
# 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_23d
_database_code_depnum_ccdc_archive 'CCDC 2051050'
loop_
_audit_author_name
_audit_author_address
'Felix Hennersdorf'
;TU Dresden
Germany
;
_audit_update_record             
;
2020-12-17 deposited with the CCDC.	2021-04-01 downloaded from the CCDC.
;
_audit_creation_date             2017-09-21
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C10 H11 F3 N2 O2 S'
_chemical_formula_sum            'C10 H11 F3 N2 O2 S'
_chemical_formula_weight         280.27
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C20 H22 N4 O4 F6 S2 '
_chemical_oxdiff_usercomment     'C10 H11 N2 O2 S F3'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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                   6.5646(3)
_cell_length_b                   8.3986(3)
_cell_length_c                   11.3918(6)
_cell_angle_alpha                105.687(4)
_cell_angle_beta                 96.554(4)
_cell_angle_gamma                98.490(4)
_cell_volume                     590.16(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2873
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      76.3200
_cell_measurement_theta_min      4.0800
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.821
_exptl_absorpt_correction_T_max  0.916
_exptl_absorpt_correction_T_min  0.735
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.577
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             288
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
2 5 -1 0.0389
1 5 -2 0.0342
0 5 -3 0.0342
-3 -3 0 0.0590
0 -5 3 0.0621
3 -2 4 0.0832
-3 2 -4 0.0742
2 4 -4 0.0314
0 3 -7 0.0348
2 -2 6 0.0710
-1 -4 6 0.0540
2 -1 -7 0.0166
-2 1 7 0.0166

_exptl_crystal_size_max          0.172
_exptl_crystal_size_mid          0.096
_exptl_crystal_size_min          0.033
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
2.0025 4.9966 -0.9979 -0.7549 -0.5237 -0.6469
1.0037 4.9977 -2.0005 -0.7536 -0.5410 -0.3489
0.0050 4.9987 -3.0032 -0.7524 -0.5584 -0.0509
-3.0005 -2.9957 -0.0063 0.3983 0.4123 0.8285
-0.0050 -4.9987 3.0032 0.7524 0.5584 0.0509
2.9944 -2.0027 4.0093 0.3068 0.2538 -0.8575
-2.9944 2.0027 -4.0093 -0.3068 -0.2538 0.8575
2.0054 3.9958 -3.9965 -0.4340 -0.7998 -0.3487
0.0088 2.9976 -7.0009 -0.2053 -0.8952 0.3855
1.9923 -2.0007 6.0060 0.1660 0.5597 -0.7996
-1.0078 -3.9965 5.9990 0.3854 0.9249 -0.0293
2.0070 -1.0048 -6.9922 0.6025 -0.8878 0.1824
-2.0070 1.0048 6.9922 -0.6025 0.8878 -0.1824

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0188
_diffrn_reflns_av_unetI/netI     0.0283
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            4954
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.425
_diffrn_reflns_theta_min         4.085
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2850
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -50.00  33.00   0.50    1.00    --  -38.50  38.00   0.00  166
  2  ω    -61.00  29.00   0.50    1.00    --  -38.50  57.00-150.00  180
  3  ω     45.00  82.00   0.50    1.00    --   42.50 -99.00 -30.00   74
  4  ω     42.00 108.00   0.50    4.00    --  111.00 -61.00  60.00  132
  5  ω    114.00 139.00   0.50    4.00    --  111.00 -61.00  60.00   50
  6  ω     95.00 121.00   0.50    4.00    --  111.00-125.00  90.00   52
  7  ω     80.00 109.00   0.50    4.00    --  111.00 -94.00 120.00   58
  8  ω     75.00 119.00   0.50    4.00    --  111.00-125.00   0.00   88
  9  ω     74.00 118.00   0.50    4.00    --  111.00-125.00-120.00   88
 10  ω     96.00 139.00   0.50    4.00    --  111.00 -77.00-180.00   86
 11  ω     78.00 109.00   0.50    4.00    --  111.00 -94.00-150.00   62
 12  ω     42.00  69.00   0.50    4.00    --  111.00 -30.00 -90.00   54
 13  ω     42.00 134.00   0.50    4.00    --  111.00 -77.00 -30.00  184
 14  ω     92.00 173.00   0.50    4.00    --  111.00  30.00-120.00  162
 15  ω     88.00 178.00   0.50    4.00    --  111.00  45.00-180.00  180
 16  ω    146.00 173.00   0.50    4.00    --  111.00  61.00  60.00   54
 17  ω    122.00 177.00   0.50    4.00    --  111.00  45.00  90.00  110
 18  ω     92.00 175.00   0.50    4.00    --  111.00  30.00 150.00  166
 19  ω     86.00 119.00   0.50    4.00    --  111.00  61.00  60.00   66
 20  ω     92.00 117.00   0.50    4.00    --  111.00  45.00  90.00   50
 21  ω     30.00  64.00   0.50    4.00    --  111.00 -94.00  30.00   68
 22  ω      7.00  50.00   0.50    1.00    --   42.50 -99.00 -90.00   86
 23  ω     46.00 132.00   0.50    4.00    --  111.00 -45.00-180.00  172
 24  ω     33.00  63.00   0.50    4.00    --  111.00 -94.00-150.00   60
 25  ω   -108.00 -14.00   0.50    1.00    --  -38.50 -57.00  60.00  188
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0460092000
_diffrn_orient_matrix_UB_12      -0.1789476000
_diffrn_orient_matrix_UB_13      -0.0472385000
_diffrn_orient_matrix_UB_21      -0.0907665000
_diffrn_orient_matrix_UB_22      -0.0469355000
_diffrn_orient_matrix_UB_23      0.1076558000
_diffrn_orient_matrix_UB_31      -0.2178520000
_diffrn_orient_matrix_UB_32      -0.0581848000
_diffrn_orient_matrix_UB_33      -0.0802497000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2298
_reflns_number_total             2450
_reflns_odcompleteness_completeness 99.83
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_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 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_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         0.476
_refine_diff_density_min         -0.524
_refine_diff_density_rms         0.061
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     193
_refine_ls_number_reflns         2450
_refine_ls_number_restraints     57
_refine_ls_R_factor_all          0.0408
_refine_ls_R_factor_gt           0.0387
_refine_ls_restrained_S_all      1.142
_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)+(0.0544P)²+0.4385P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1021
_refine_ls_wR_factor_ref         0.1043
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 F1A-C7 \\sim F1B-C7 \\sim F2A-C7 \\sim F2B-C7 \\sim F3B-C7 \\sim F3A-C7
 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
F1A \\sim F1B \\sim F2A \\sim F2B \\sim F3A \\sim F3B: within 2A with sigma of
0.01 and sigma for terminal atoms of 0.02
4. Others
 Sof(F1B)=Sof(F2B)=Sof(F3B)=1-FVAR(1)
 Sof(F1A)=Sof(F2A)=Sof(F3A)=FVAR(1)
5.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C8(H8)
5.b Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C10(H10A,H10B,H10C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.19285(6) 0.26173(5) 0.81340(3) 0.01678(14) Uani 1 1 d . . . . .
F1A F 0.8077(4) 0.2205(6) 0.3812(4) 0.0555(12) Uani 0.792(7) 1 d D U P A 1
F1B F 0.782(2) 0.167(2) 0.3587(19) 0.057(4) Uani 0.208(7) 1 d D U P A 2
F2A F 0.5194(4) 0.0981(3) 0.26674(17) 0.0440(6) Uani 0.792(7) 1 d D U P A 1
F2B F 0.4958(13) 0.197(2) 0.2609(7) 0.072(4) Uani 0.208(7) 1 d D U P A 2
F3A F 0.5858(5) 0.3637(3) 0.3280(2) 0.0486(8) Uani 0.792(7) 1 d D U P A 1
F3B F 0.717(2) 0.3926(8) 0.3805(11) 0.068(3) Uani 0.208(7) 1 d D U P A 2
O1 O 0.3506(2) 0.28801(16) 0.91995(11) 0.0215(3) Uani 1 1 d . . . . .
O2 O 0.0297(2) 0.11561(15) 0.78330(12) 0.0227(3) Uani 1 1 d . . . . .
N1 N 0.0811(2) 0.42165(18) 0.82032(13) 0.0181(3) Uani 1 1 d . . . . .
N2 N 0.1205(2) 0.70957(18) 0.89923(13) 0.0180(3) Uani 1 1 d . . . . .
C1 C 0.3227(3) 0.2450(2) 0.68332(15) 0.0172(3) Uani 1 1 d . . . . .
C2 C 0.5371(3) 0.2948(2) 0.69864(16) 0.0205(4) Uani 1 1 d . . . . .
H2 H 0.6164 0.3324 0.7773 0.025 Uiso 1 1 calc R . . . .
C3 C 0.6323(3) 0.2879(2) 0.59497(17) 0.0228(4) Uani 1 1 d . . . . .
H3 H 0.7759 0.3224 0.6039 0.027 Uiso 1 1 calc R . . . .
C4 C 0.5124(3) 0.2294(2) 0.47781(16) 0.0215(4) Uani 1 1 d . . . . .
C5 C 0.2975(3) 0.1754(2) 0.46305(16) 0.0234(4) Uani 1 1 d . . . . .
H5 H 0.2186 0.1338 0.3844 0.028 Uiso 1 1 calc R . . . .
C6 C 0.2026(3) 0.1840(2) 0.56606(16) 0.0220(4) Uani 1 1 d . . . . .
H6 H 0.0590 0.1492 0.5572 0.026 Uiso 1 1 calc R . . . .
C7 C 0.6120(3) 0.2322(2) 0.36641(18) 0.0274(4) Uani 1 1 d D . . . .
C8 C 0.1891(3) 0.5689(2) 0.89106(15) 0.0173(3) Uani 1 1 d . . . . .
H8 H 0.3177 0.5725 0.9364 0.021 Uiso 1 1 calc R . . . .
C9 C 0.2387(3) 0.8701(2) 0.98179(16) 0.0219(4) Uani 1 1 d . . . . .
H9A H 0.1625 0.9114 1.0472 0.033 Uiso 1 1 calc GR . . . .
H9B H 0.2593 0.9502 0.9360 0.033 Uiso 1 1 calc GR . . . .
H9C H 0.3717 0.8539 1.0163 0.033 Uiso 1 1 calc GR . . . .
C10 C -0.0814(3) 0.7129(2) 0.83192(17) 0.0223(4) Uani 1 1 d . . . . .
H10A H -0.1141 0.6212 0.7570 0.034 Uiso 1 1 calc GR . . . .
H10B H -0.0752 0.8175 0.8123 0.034 Uiso 1 1 calc GR . . . .
H10C H -0.1874 0.7020 0.8822 0.034 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O1 1.4474(12) . ?
S1 O2 1.4392(13) . ?
S1 N1 1.6109(15) . ?
S1 C1 1.7759(17) . ?
F1A C7 1.298(3) . ?
F1B C7 1.313(7) . ?
F2A C7 1.370(3) . ?
F2B C7 1.283(6) . ?
F3A C7 1.319(3) . ?
F3B C7 1.378(7) . ?
N1 C8 1.324(2) . ?
N2 C8 1.309(2) . ?
N2 C9 1.464(2) . ?
N2 C10 1.461(2) . ?
C1 C2 1.385(2) . ?
C1 C6 1.392(2) . ?
C2 H2 0.9300 . ?
C2 C3 1.389(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.390(3) . ?
C4 C5 1.393(3) . ?
C4 C7 1.496(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.380(3) . ?
C6 H6 0.9300 . ?
C8 H8 0.9300 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 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 112.76(7) . . ?
O1 S1 C1 107.23(8) . . ?
O2 S1 O1 117.49(8) . . ?
O2 S1 N1 107.02(8) . . ?
O2 S1 C1 107.13(8) . . ?
N1 S1 C1 104.29(8) . . ?
C8 N1 S1 116.15(12) . . ?
C8 N2 C9 121.12(15) . . ?
C8 N2 C10 121.87(14) . . ?
C10 N2 C9 116.94(14) . . ?
C2 C1 S1 120.68(13) . . ?
C2 C1 C6 121.12(16) . . ?
C6 C1 S1 118.19(13) . . ?
C1 C2 H2 120.4 . . ?
C1 C2 C3 119.11(16) . . ?
C3 C2 H2 120.4 . . ?
C2 C3 H3 120.0 . . ?
C2 C3 C4 119.90(17) . . ?
C4 C3 H3 120.0 . . ?
C3 C4 C5 120.61(17) . . ?
C3 C4 C7 120.11(17) . . ?
C5 C4 C7 119.21(16) . . ?
C4 C5 H5 120.3 . . ?
C6 C5 C4 119.50(16) . . ?
C6 C5 H5 120.3 . . ?
C1 C6 H6 120.1 . . ?
C5 C6 C1 119.72(17) . . ?
C5 C6 H6 120.1 . . ?
F1A C7 F2A 104.9(2) . . ?
F1A C7 F3A 110.9(3) . . ?
F1A C7 C4 113.2(3) . . ?
F1B C7 F3B 93.4(10) . . ?
F1B C7 C4 115.9(9) . . ?
F2A C7 C4 111.34(17) . . ?
F2B C7 F1B 112.2(10) . . ?
F2B C7 F3B 102.2(8) . . ?
F2B C7 C4 119.2(5) . . ?
F3A C7 F2A 103.4(2) . . ?
F3A C7 C4 112.38(17) . . ?
F3B C7 C4 109.7(4) . . ?
N1 C8 H8 119.0 . . ?
N2 C8 N1 122.08(15) . . ?
N2 C8 H8 119.0 . . ?
N2 C9 H9A 109.5 . . ?
N2 C9 H9B 109.5 . . ?
N2 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N2 C10 H10A 109.5 . . ?
N2 C10 H10B 109.5 . . ?
N2 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.322
_oxdiff_exptl_absorpt_empirical_full_min 0.809
####################################################################### 
# 
# 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_19
_database_code_depnum_ccdc_archive 'CCDC 2051051'
loop_
_audit_author_name
_audit_author_address
'Felix Hennersdorf'
;TU Dresden
Germany
;
_audit_update_record             
;
2020-12-17 deposited with the CCDC.	2021-04-01 downloaded from the CCDC.
;
_audit_creation_date             2019-08-21
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H18 N2 O2 S'
_chemical_formula_sum            'C20 H18 N2 O2 S'
_chemical_formula_weight         350.42
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C40 H36 N4 O4 S2 '
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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                   9.37570(10)
_cell_length_b                   10.2532(2)
_cell_length_c                   11.0768(2)
_cell_angle_alpha                115.593(2)
_cell_angle_beta                 91.0640(10)
_cell_angle_gamma                113.686(2)
_cell_volume                     855.33(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4025
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      76.3940
_cell_measurement_theta_min      5.0880
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.808
_exptl_absorpt_correction_T_max  0.824
_exptl_absorpt_correction_T_min  0.700
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.361
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             368
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-3 5 -1 0.1263
3 -5 1 0.1261
4 2 -3 0.1207
0 -1 5 0.0816
4 2 -1 0.1135
-2 -1 1 0.1039
1 1 -5 0.0797
3 1 4 0.0784
0 1 -5 0.0652
-3 -1 -4 0.0733
4 -1 5 0.0986
-4 1 -5 0.0742
0 2 -5 0.0813
-2 2 -5 0.0684
2 -5 5 0.1278
5 -3 2 0.1059
-3 5 -5 0.0918
4 -4 -3 0.1019
-5 1 3 0.1226
-3 5 2 0.1139
2 -2 -5 0.0821
0 0 -6 0.0648

_exptl_crystal_size_max          0.262
_exptl_crystal_size_mid          0.219
_exptl_crystal_size_min          0.147
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-3.0023 4.9991 -0.9986 0.7477 -0.2703 0.0445
3.0023 -4.9991 0.9986 -0.7477 0.2703 -0.0445
4.0004 1.9992 -3.0005 -0.0254 -0.0234 0.9090
-0.0012 -1.0030 5.0023 0.2638 0.6465 -0.1842
3.9997 1.9978 -0.9995 0.1417 0.2442 0.8768
-2.0000 -0.9992 1.0000 -0.0291 -0.0552 -0.4465
1.0013 1.0025 -5.0022 -0.2844 -0.5633 0.3475
2.9985 0.9953 4.0028 0.4261 0.8075 0.5293
0.0012 1.0030 -5.0023 -0.2638 -0.6465 0.1842
-2.9985 -0.9953 -4.0028 -0.4261 -0.8075 -0.5293
3.9992 -1.0047 5.0025 0.1812 0.9793 0.4692
-3.9992 1.0047 -5.0025 -0.1812 -0.9793 -0.4692
0.0007 2.0024 -5.0019 -0.1099 -0.6239 0.2878
-1.9995 2.0033 -5.0020 -0.0686 -0.7903 -0.0388
2.0009 -5.0015 5.0007 -0.3929 0.7224 -0.2722
5.0012 -3.0019 2.0001 -0.3977 0.6158 0.4735
-3.0009 5.0019 -5.0008 0.4136 -0.8056 0.1088
4.0032 -3.9973 -3.0031 -0.9485 -0.1591 0.2870
-5.0019 0.9995 3.0018 0.5076 0.0081 -0.7613
-3.0033 4.9970 2.0030 0.9982 0.1312 -0.0038
2.0028 -1.9962 -5.0034 -0.7666 -0.5480 0.1998
0.0020 0.0043 -6.0033 -0.5012 -0.8029 0.0966

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0208
_diffrn_reflns_av_unetI/netI     0.0261
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7531
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.746
_diffrn_reflns_theta_min         4.551
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.5700
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -18.00  34.00   0.50    0.50    --  -38.50  38.00  60.00  104
  2  ω    -64.00  30.00   0.50    0.50    --  -38.50  57.00 -90.00  188
  3  ω     43.00  70.00   0.50    0.50    --   42.50 -99.00   0.00   54
  4  ω     28.00  96.00   0.50    0.50    --   42.50-125.00  90.00  136
  5  ω     52.00 129.00   0.50    1.00    --  111.00 -30.00 -30.00  154
  6  ω     87.00 118.00   0.50    1.00    --  111.00 -61.00 -30.00   62
  7  ω     94.00 121.00   0.50    1.00    --  111.00-125.00  60.00   54
  8  ω     66.00 109.00   0.50    1.00    --  111.00 -94.00  90.00   86
  9  ω     66.00 104.00   0.50    1.00    --  111.00 -45.00 120.00   76
 10  ω     88.00 115.00   0.50    1.00    --  111.00  15.00  60.00   54
 11  ω    138.00 178.00   0.50    1.00    --  111.00  30.00 150.00   80
 12  ω    135.00 178.00   0.50    1.00    --  111.00 125.00  30.00   86
 13  ω     87.00 171.00   0.50    1.00    --  111.00  30.00-150.00  168
 14  ω     87.00 178.00   0.50    1.00    --  111.00  45.00 -60.00  182
 15  ω     86.00 131.00   0.50    1.00    --  111.00 -61.00-150.00   90
 16  ω     67.00 109.00   0.50    1.00    --  111.00 -94.00-150.00   84
 17  ω     53.00  84.00   0.50    1.00    --  111.00 -61.00-150.00   62
 18  ω     45.00  73.00   0.50    1.00    --  111.00-125.00-180.00   56
 19  ω     47.00 121.00   0.50    1.00    --  111.00-125.00-150.00  148
 20  ω     44.00 117.00   0.50    1.00    --  111.00-122.00  17.00  146
 21  ω     40.00  75.00   0.50    1.00    --  111.00 -94.00 120.00   70
 22  ω     30.00 107.00   0.50    1.00    --  111.00 -94.00  30.00  154
 23  ω     84.00 178.00   0.50    1.00    --  111.00  61.00-120.00  188
 24  ω   -109.00 -14.00   0.50    0.50    --  -38.50 -57.00 120.00  190
 25  ω   -104.00 -58.00   0.50    0.50    --  -38.50-151.00-143.00   92
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0205654000
_diffrn_orient_matrix_UB_12      0.1539042000
_diffrn_orient_matrix_UB_13      0.0835821000
_diffrn_orient_matrix_UB_21      0.0831964000
_diffrn_orient_matrix_UB_22      0.0226179000
_diffrn_orient_matrix_UB_23      0.1337929000
_diffrn_orient_matrix_UB_31      0.1633760000
_diffrn_orient_matrix_UB_32      0.1038213000
_diffrn_orient_matrix_UB_33      -0.0159624000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3301
_reflns_number_total             3540
_reflns_odcompleteness_completeness 99.87
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_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         0.383
_refine_diff_density_min         -0.565
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3540
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0380
_refine_ls_R_factor_gt           0.0355
_refine_ls_restrained_S_all      1.039
_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)+(0.0497P)²+0.3180P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0904
_refine_ls_wR_factor_ref         0.0927
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C10(H10), C11(H11), C12(H12),
 C13(H13), C14(H14), C16(H16), C17(H17), C18(H18), C19(H19), C20(H20)
2.b Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.78683(17) 0.75809(16) 0.25277(14) 0.0202(3) Uani 1 1 d . . . . .
C2 C 0.7189(2) 0.6745(2) 0.11292(16) 0.0299(3) Uani 1 1 d . . . . .
H2 H 0.6130 0.6469 0.0814 0.036 Uiso 1 1 calc R . . . .
C3 C 0.8108(3) 0.6323(2) 0.02020(18) 0.0423(5) Uani 1 1 d . . . . .
H3 H 0.7665 0.5767 -0.0739 0.051 Uiso 1 1 calc R . . . .
C4 C 0.9681(3) 0.6729(2) 0.0679(2) 0.0412(4) Uani 1 1 d . . . . .
H4 H 1.0299 0.6465 0.0056 0.049 Uiso 1 1 calc R . . . .
C5 C 1.0340(2) 0.7529(2) 0.2084(2) 0.0337(4) Uani 1 1 d . . . . .
H5 H 1.1391 0.7775 0.2396 0.040 Uiso 1 1 calc R . . . .
C6 C 0.94412(17) 0.79640(17) 0.30250(16) 0.0247(3) Uani 1 1 d . . . . .
H6 H 0.9877 0.8499 0.3966 0.030 Uiso 1 1 calc R . . . .
C7 C 0.64163(15) 0.81685(16) 0.58887(14) 0.0177(3) Uani 1 1 d . . . . .
C8 C 0.53772(17) 0.90185(18) 0.61783(15) 0.0220(3) Uani 1 1 d . . . . .
H8A H 0.4297 0.8249 0.5661 0.033 Uiso 1 1 calc GR . . . .
H8B H 0.5773 0.9854 0.5915 0.033 Uiso 1 1 calc GR . . . .
H8C H 0.5399 0.9494 0.7143 0.033 Uiso 1 1 calc GR . . . .
C9 C 0.59130(16) 0.78207(16) 0.79222(14) 0.0189(3) Uani 1 1 d . . . . .
C10 C 0.67620(17) 0.89559(17) 0.92681(15) 0.0223(3) Uani 1 1 d . . . . .
H10 H 0.7829 0.9693 0.9454 0.027 Uiso 1 1 calc R . . . .
C11 C 0.60018(18) 0.89797(18) 1.03346(15) 0.0252(3) Uani 1 1 d . . . . .
H11 H 0.6561 0.9739 1.1240 0.030 Uiso 1 1 calc R . . . .
C12 C 0.44090(18) 0.78750(19) 1.00562(15) 0.0245(3) Uani 1 1 d . . . . .
H12 H 0.3908 0.7890 1.0775 0.029 Uiso 1 1 calc R . . . .
C13 C 0.35674(17) 0.67518(18) 0.87100(15) 0.0235(3) Uani 1 1 d . . . . .
H13 H 0.2499 0.6021 0.8527 0.028 Uiso 1 1 calc R . . . .
C14 C 0.43143(16) 0.67123(17) 0.76294(14) 0.0216(3) Uani 1 1 d . . . . .
H14 H 0.3753 0.5956 0.6724 0.026 Uiso 1 1 calc R . . . .
C15 C 0.77918(15) 0.69999(16) 0.66862(13) 0.0179(3) Uani 1 1 d . . . . .
C16 C 0.94042(16) 0.78578(17) 0.67443(15) 0.0222(3) Uani 1 1 d . . . . .
H16 H 0.9800 0.8888 0.6824 0.027 Uiso 1 1 calc R . . . .
C17 C 1.04119(16) 0.71530(18) 0.66819(16) 0.0245(3) Uani 1 1 d . . . . .
H17 H 1.1488 0.7711 0.6711 0.029 Uiso 1 1 calc R . . . .
C18 C 0.98270(17) 0.56204(18) 0.65763(15) 0.0231(3) Uani 1 1 d . . . . .
H18 H 1.0511 0.5158 0.6539 0.028 Uiso 1 1 calc R . . . .
C19 C 0.82210(17) 0.47797(17) 0.65272(15) 0.0224(3) Uani 1 1 d . . . . .
H19 H 0.7829 0.3756 0.6461 0.027 Uiso 1 1 calc R . . . .
C20 C 0.71972(16) 0.54692(17) 0.65762(14) 0.0201(3) Uani 1 1 d . . . . .
H20 H 0.6119 0.4904 0.6535 0.024 Uiso 1 1 calc R . . . .
N1 N 0.70328(13) 0.78059(14) 0.48103(12) 0.0187(2) Uani 1 1 d . . . . .
N2 N 0.67304(13) 0.77339(14) 0.68149(12) 0.0185(2) Uani 1 1 d . . . . .
O1 O 0.51143(11) 0.75040(13) 0.29393(11) 0.0236(2) Uani 1 1 d . . . . .
O2 O 0.75478(12) 1.00809(12) 0.42468(10) 0.0223(2) Uani 1 1 d . . . . .
S1 S 0.67688(3) 0.83348(4) 0.36761(3) 0.01693(10) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.385(2) . ?
C1 C6 1.396(2) . ?
C1 S1 1.7658(14) . ?
C2 H2 0.9300 . ?
C2 C3 1.390(2) . ?
C3 H3 0.9300 . ?
C3 C4 1.384(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.390(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.389(2) . ?
C6 H6 0.9300 . ?
C7 C8 1.5046(19) . ?
C7 N1 1.3091(18) . ?
C7 N2 1.3518(18) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 C10 1.387(2) . ?
C9 C14 1.3922(19) . ?
C9 N2 1.4474(17) . ?
C10 H10 0.9300 . ?
C10 C11 1.387(2) . ?
C11 H11 0.9300 . ?
C11 C12 1.389(2) . ?
C12 H12 0.9300 . ?
C12 C13 1.384(2) . ?
C13 H13 0.9300 . ?
C13 C14 1.3916(19) . ?
C14 H14 0.9300 . ?
C15 C16 1.3937(18) . ?
C15 C20 1.3850(19) . ?
C15 N2 1.4461(17) . ?
C16 H16 0.9300 . ?
C16 C17 1.388(2) . ?
C17 H17 0.9300 . ?
C17 C18 1.389(2) . ?
C18 H18 0.9300 . ?
C18 C19 1.388(2) . ?
C19 H19 0.9300 . ?
C19 C20 1.392(2) . ?
C20 H20 0.9300 . ?
N1 S1 1.6182(12) . ?
O1 S1 1.4452(10) . ?
O2 S1 1.4466(10) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 121.32(14) . . ?
C2 C1 S1 118.33(12) . . ?
C6 C1 S1 120.06(11) . . ?
C1 C2 H2 120.3 . . ?
C1 C2 C3 119.30(16) . . ?
C3 C2 H2 120.3 . . ?
C2 C3 H3 120.0 . . ?
C4 C3 C2 120.04(17) . . ?
C4 C3 H3 120.0 . . ?
C3 C4 H4 119.8 . . ?
C3 C4 C5 120.31(15) . . ?
C5 C4 H4 119.8 . . ?
C4 C5 H5 119.8 . . ?
C6 C5 C4 120.41(16) . . ?
C6 C5 H5 119.8 . . ?
C1 C6 H6 120.7 . . ?
C5 C6 C1 118.59(15) . . ?
C5 C6 H6 120.7 . . ?
N1 C7 C8 125.44(12) . . ?
N1 C7 N2 117.30(12) . . ?
N2 C7 C8 117.26(12) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C10 C9 C14 120.98(13) . . ?
C10 C9 N2 119.26(12) . . ?
C14 C9 N2 119.67(12) . . ?
C9 C10 H10 120.4 . . ?
C9 C10 C11 119.26(13) . . ?
C11 C10 H10 120.4 . . ?
C10 C11 H11 119.8 . . ?
C10 C11 C12 120.31(14) . . ?
C12 C11 H11 119.8 . . ?
C11 C12 H12 120.0 . . ?
C13 C12 C11 120.08(13) . . ?
C13 C12 H12 120.0 . . ?
C12 C13 H13 119.9 . . ?
C12 C13 C14 120.26(13) . . ?
C14 C13 H13 119.9 . . ?
C9 C14 H14 120.4 . . ?
C13 C14 C9 119.11(13) . . ?
C13 C14 H14 120.4 . . ?
C16 C15 N2 120.29(12) . . ?
C20 C15 C16 120.75(13) . . ?
C20 C15 N2 118.88(12) . . ?
C15 C16 H16 120.5 . . ?
C17 C16 C15 119.08(13) . . ?
C17 C16 H16 120.5 . . ?
C16 C17 H17 119.7 . . ?
C16 C17 C18 120.56(13) . . ?
C18 C17 H17 119.7 . . ?
C17 C18 H18 120.0 . . ?
C19 C18 C17 119.92(14) . . ?
C19 C18 H18 120.0 . . ?
C18 C19 H19 120.0 . . ?
C18 C19 C20 119.98(13) . . ?
C20 C19 H19 120.0 . . ?
C15 C20 C19 119.71(12) . . ?
C15 C20 H20 120.1 . . ?
C19 C20 H20 120.1 . . ?
C7 N1 S1 120.62(10) . . ?
C7 N2 C9 122.45(11) . . ?
C7 N2 C15 122.05(11) . . ?
C15 N2 C9 115.23(11) . . ?
N1 S1 C1 100.47(6) . . ?
O1 S1 C1 108.10(7) . . ?
O1 S1 N1 112.36(6) . . ?
O1 S1 O2 115.97(6) . . ?
O2 S1 C1 107.07(6) . . ?
O2 S1 N1 111.51(6) . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.242
_oxdiff_exptl_absorpt_empirical_full_min 0.786
####################################################################### 
# 
# 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_9a[OTf]
_database_code_depnum_ccdc_archive 'CCDC 2051046'
loop_
_audit_author_name
_audit_author_address
'Felix Hennersdorf'
;TU Dresden
Germany
;
_audit_update_record             
;
2020-12-17 deposited with the CCDC.	2021-04-01 downloaded from the CCDC.
;
_audit_creation_date             2018-01-04
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H7 F16 N O P, C F3 O3 S'
_chemical_formula_sum            'C22 H7 F19 N O4 P S'
_chemical_formula_weight         773.32
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C22 H7 F18 N O4 P S'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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                   8.82043(6)
_cell_length_b                   15.38084(11)
_cell_length_c                   19.59298(12)
_cell_angle_alpha                90
_cell_angle_beta                 93.0239(6)
_cell_angle_gamma                90
_cell_volume                     2654.39(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    11629
_cell_measurement_temperature    100.00(19)
_cell_measurement_theta_max      76.4090
_cell_measurement_theta_min      2.2510
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    3.268
_exptl_absorpt_correction_T_max  0.523
_exptl_absorpt_correction_T_min  0.341
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.935
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1520
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -5 -1 0.1790
0 5 1 0.1790
-1 1 -5 0.1941
1 -1 5 0.1941
-5 1 2 0.1418
5 -1 -2 0.1418
-1 -3 -5 0.2085
1 3 5 0.2085
-1 5 -2 0.1778
1 -5 2 0.1778
1 -1 -5 0.1990
-2 4 5 0.1820

_exptl_crystal_size_max          0.477
_exptl_crystal_size_mid          0.399
_exptl_crystal_size_min          0.284
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-0.0008 -4.9986 -0.9963 -0.1478 -0.4734 0.1041
0.0008 4.9986 0.9963 0.1478 0.4734 -0.1041
-0.9983 0.9976 -5.0016 -0.0088 0.1359 0.4291
0.9983 -0.9976 5.0016 0.0088 -0.1359 -0.4291
-4.9961 1.0043 1.9896 0.8263 -0.0654 0.3115
4.9961 -1.0043 -1.9896 -0.8263 0.0654 -0.3115
-0.9991 -3.0009 -4.9988 -0.0986 -0.2533 0.4572
0.9991 3.0009 4.9988 0.0986 0.2533 -0.4572
-0.9980 4.9977 -2.0050 0.1877 0.4857 0.1941
0.9980 -4.9977 2.0050 -0.1877 -0.4857 -0.1941
0.9997 -1.0031 -4.9965 -0.3468 -0.0042 0.2606
-1.9983 4.0026 4.9925 0.5607 0.2689 -0.1904

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0238
_diffrn_reflns_av_unetI/netI     0.0220
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            15070
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.665
_diffrn_reflns_theta_min         3.655
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(19)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2850
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -87.00 -13.00   0.50    0.50    --  -38.50 125.00 150.00  148
  2  ω   -109.00 -69.00   0.50    0.50    --  -38.50 -38.00 -98.00   80
  3  ω   -112.00 -10.00   0.50    0.50    --  -38.50 -77.00  30.00  204
  4  ω     37.00 135.00   0.50    0.75    --  111.00 -30.00 120.00  196
  5  ω     76.00 118.00   0.50    0.75    --  111.00-126.00  38.00   84
  6  ω     39.00 120.00   0.50    0.75    --  111.00-125.00 120.00  162
  7  ω     40.00  70.00   0.50    0.75    --  111.00-126.00  38.00   60
  8  ω     39.00  85.00   0.50    0.75    --  111.00 -94.00 120.00   92
  9  ω     30.00  93.00   0.50    0.75    --  111.00 -94.00  30.00  126
 10  ω    121.00 175.00   0.50    0.75    --  111.00  15.00 -30.00  108
 11  ω    120.00 167.00   0.50    0.75    --  111.00 125.00 -60.00   94
 12  ω     95.00 122.00   0.50    0.75    --  111.00 125.00   0.00   54
 13  ω     96.00 173.00   0.50    0.75    --  111.00 125.00  60.00  154
 14  ω     72.00  97.00   0.50    0.75    --  111.00  15.00 -30.00   50
 15  ω    100.00 127.00   0.50    0.75    --  111.00 -45.00-150.00   54
 16  ω     42.00 118.00   0.50    0.75    --  111.00-125.00-180.00  152
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1467086000
_diffrn_orient_matrix_UB_12      0.0225140000
_diffrn_orient_matrix_UB_13      0.0355385000
_diffrn_orient_matrix_UB_21      0.0273865000
_diffrn_orient_matrix_UB_22      0.0973449000
_diffrn_orient_matrix_UB_23      -0.0132308000
_diffrn_orient_matrix_UB_31      -0.0912432000
_diffrn_orient_matrix_UB_32      -0.0070622000
_diffrn_orient_matrix_UB_33      -0.0689875000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5402
_reflns_number_total             5520
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_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         0.498
_refine_diff_density_min         -0.495
_refine_diff_density_rms         0.076
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.108
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     439
_refine_ls_number_reflns         5520
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0360
_refine_ls_R_factor_gt           0.0351
_refine_ls_restrained_S_all      1.108
_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)+(0.0487P)²+1.5115P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0901
_refine_ls_wR_factor_ref         0.0908
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.5 times of:
  All C(H,H,H) groups
2.a Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C21(H21A,H21B,H21C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P 0.44127(4) 0.32459(2) 0.51770(2) 0.01029(9) Uani 1 1 d . . . . .
F1 F 0.51213(10) 0.41046(6) 0.48195(4) 0.01369(18) Uani 1 1 d . . . . .
F2 F 0.64570(10) 0.42421(6) 0.61714(5) 0.01618(19) Uani 1 1 d . . . . .
F3 F 0.92820(11) 0.38479(7) 0.66469(5) 0.0216(2) Uani 1 1 d . . . . .
F4 F 1.06605(11) 0.23858(7) 0.62146(5) 0.0222(2) Uani 1 1 d . . . . .
F5 F 0.91794(11) 0.12956(7) 0.53192(5) 0.0217(2) Uani 1 1 d . . . . .
F6 F 0.62838(11) 0.16628(6) 0.48652(5) 0.0174(2) Uani 1 1 d . . . . .
F7 F 0.22691(11) 0.46521(6) 0.46948(5) 0.0175(2) Uani 1 1 d . . . . .
F8 F 0.08446(12) 0.58358(7) 0.54226(6) 0.0238(2) Uani 1 1 d . . . . .
F9 F 0.09662(13) 0.57435(7) 0.68090(6) 0.0284(2) Uani 1 1 d . . . . .
F10 F 0.26041(13) 0.44614(7) 0.74608(5) 0.0245(2) Uani 1 1 d . . . . .
F11 F 0.41224(11) 0.33101(6) 0.67501(5) 0.01590(19) Uani 1 1 d . . . . .
F12 F 0.60482(11) 0.29950(7) 0.38717(5) 0.0204(2) Uani 1 1 d . . . . .
F13 F 0.48511(14) 0.26511(8) 0.26151(5) 0.0282(2) Uani 1 1 d . . . . .
F14 F 0.18280(15) 0.23986(8) 0.24060(5) 0.0307(3) Uani 1 1 d . . . . .
F15 F -0.00082(12) 0.24194(7) 0.34798(6) 0.0263(2) Uani 1 1 d . . . . .
F16 F 0.11666(10) 0.27486(6) 0.47460(5) 0.0177(2) Uani 1 1 d . . . . .
O1 O 0.37018(12) 0.23381(7) 0.56326(5) 0.0127(2) Uani 1 1 d . . . . .
N00Q N 0.29988(15) 0.09884(9) 0.59133(7) 0.0143(3) Uani 1 1 d . . . . .
C1 C 0.62967(17) 0.29544(10) 0.55099(7) 0.0123(3) Uani 1 1 d . . . . .
C2 C 0.70961(17) 0.35092(10) 0.59570(8) 0.0135(3) Uani 1 1 d . . . . .
C3 C 0.85517(18) 0.33159(11) 0.62031(8) 0.0154(3) Uani 1 1 d . . . . .
C4 C 0.92423(18) 0.25660(11) 0.59871(8) 0.0167(3) Uani 1 1 d . . . . .
C5 C 0.84850(18) 0.20077(11) 0.55353(8) 0.0161(3) Uani 1 1 d . . . . .
C6 C 0.70148(18) 0.22021(10) 0.53078(8) 0.0142(3) Uani 1 1 d . . . . .
C7 C 0.32535(17) 0.39323(10) 0.56913(8) 0.0125(3) Uani 1 1 d . . . . .
C8 C 0.23911(17) 0.45931(10) 0.53758(8) 0.0141(3) Uani 1 1 d . . . . .
C9 C 0.16380(18) 0.52038(10) 0.57455(9) 0.0166(3) Uani 1 1 d . . . . .
C10 C 0.17074(19) 0.51621(11) 0.64500(9) 0.0187(3) Uani 1 1 d . . . . .
C11 C 0.25354(18) 0.45081(11) 0.67810(8) 0.0172(3) Uani 1 1 d . . . . .
C12 C 0.32903(17) 0.39040(10) 0.64030(8) 0.0135(3) Uani 1 1 d . . . . .
C13 C 0.36423(17) 0.28821(10) 0.43513(7) 0.0126(3) Uani 1 1 d . . . . .
C14 C 0.45536(19) 0.28552(10) 0.37912(8) 0.0160(3) Uani 1 1 d . . . . .
C15 C 0.3954(2) 0.26789(11) 0.31411(8) 0.0199(3) Uani 1 1 d . . . . .
C16 C 0.2410(2) 0.25476(11) 0.30366(8) 0.0211(3) Uani 1 1 d . . . . .
C17 C 0.1478(2) 0.25649(11) 0.35788(9) 0.0191(3) Uani 1 1 d . . . . .
C18 C 0.21013(18) 0.27262(10) 0.42271(8) 0.0150(3) Uani 1 1 d . . . . .
C19 C 0.32877(16) 0.15545(10) 0.54543(8) 0.0126(3) Uani 1 1 d . . . . .
C20 C 0.2473(2) 0.01120(11) 0.57202(9) 0.0215(3) Uani 1 1 d . . . . .
H20A H 0.1487 0.0014 0.5892 0.032 Uiso 1 1 calc GR . . . .
H20B H 0.3173 -0.0311 0.5912 0.032 Uiso 1 1 calc GR . . . .
H20C H 0.2413 0.0060 0.5231 0.032 Uiso 1 1 calc GR . . . .
C21 C 0.3214(2) 0.11561(11) 0.66509(8) 0.0193(3) Uani 1 1 d . . . . .
H21A H 0.3649 0.1723 0.6723 0.029 Uiso 1 1 calc GR . . . .
H21B H 0.3882 0.0725 0.6855 0.029 Uiso 1 1 calc GR . . . .
H21C H 0.2250 0.1129 0.6856 0.029 Uiso 1 1 calc GR . . . .
S1 S 0.68536(5) -0.01998(3) 0.63667(2) 0.01872(10) Uani 1 1 d . . . . .
F17 F 0.92609(15) 0.06420(9) 0.68556(7) 0.0408(3) Uani 1 1 d . . . . .
F18 F 0.88300(15) -0.05639(9) 0.73710(6) 0.0365(3) Uani 1 1 d . . . . .
F19 F 0.74532(19) 0.05578(9) 0.75478(7) 0.0450(3) Uani 1 1 d . . . . .
O2 O 0.63558(15) 0.06204(9) 0.60751(7) 0.0276(3) Uani 1 1 d . . . . .
O3 O 0.78109(18) -0.07068(9) 0.59425(7) 0.0305(3) Uani 1 1 d . . . . .
O4 O 0.57100(16) -0.06886(9) 0.66968(8) 0.0331(3) Uani 1 1 d . . . . .
C22 C 0.8163(2) 0.01241(12) 0.70719(9) 0.0248(4) Uani 1 1 d . . . . .
H19 H 0.315(2) 0.1386(13) 0.4968(10) 0.011(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
P1 F1 1.6347(9) . ?
P1 O1 1.7884(11) . ?
P1 C1 1.8093(15) . ?
P1 C7 1.8121(15) . ?
P1 C13 1.8100(15) . ?
F2 C2 1.3379(18) . ?
F3 C3 1.3348(19) . ?
F4 C4 1.3347(18) . ?
F5 C5 1.3347(19) . ?
F6 C6 1.3405(18) . ?
F7 C8 1.3361(18) . ?
F8 C9 1.3373(18) . ?
F9 C10 1.3305(19) . ?
F10 C11 1.3322(19) . ?
F11 C12 1.3352(18) . ?
F12 C14 1.3368(19) . ?
F13 C15 1.333(2) . ?
F14 C16 1.3325(19) . ?
F15 C17 1.334(2) . ?
F16 C18 1.3428(18) . ?
O1 C19 1.3017(19) . ?
N00Q C19 1.287(2) . ?
N00Q C20 1.469(2) . ?
N00Q C21 1.470(2) . ?
C1 C2 1.388(2) . ?
C1 C6 1.387(2) . ?
C2 C3 1.380(2) . ?
C3 C4 1.381(2) . ?
C4 C5 1.380(2) . ?
C5 C6 1.382(2) . ?
C7 C8 1.394(2) . ?
C7 C12 1.394(2) . ?
C8 C9 1.378(2) . ?
C9 C10 1.380(2) . ?
C10 C11 1.384(2) . ?
C11 C12 1.381(2) . ?
C13 C14 1.395(2) . ?
C13 C18 1.389(2) . ?
C14 C15 1.380(2) . ?
C15 C16 1.382(3) . ?
C16 C17 1.377(3) . ?
C17 C18 1.380(2) . ?
C19 H19 0.99(2) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
S1 O2 1.4437(13) . ?
S1 O3 1.4442(14) . ?
S1 O4 1.4387(14) . ?
S1 C22 1.8230(19) . ?
F17 C22 1.340(2) . ?
F18 C22 1.331(2) . ?
F19 C22 1.330(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
F1 P1 O1 175.38(5) . . ?
F1 P1 C1 89.43(6) . . ?
F1 P1 C7 90.42(6) . . ?
F1 P1 C13 90.04(6) . . ?
O1 P1 C1 88.06(6) . . ?
O1 P1 C7 87.39(6) . . ?
O1 P1 C13 94.57(6) . . ?
C1 P1 C7 118.58(7) . . ?
C1 P1 C13 122.68(7) . . ?
C13 P1 C7 118.74(7) . . ?
C19 O1 P1 133.61(10) . . ?
C19 N00Q C20 120.83(14) . . ?
C19 N00Q C21 123.24(14) . . ?
C20 N00Q C21 115.90(13) . . ?
C2 C1 P1 120.09(12) . . ?
C6 C1 P1 121.90(12) . . ?
C6 C1 C2 117.94(14) . . ?
F2 C2 C1 120.51(13) . . ?
F2 C2 C3 118.14(14) . . ?
C3 C2 C1 121.35(15) . . ?
F3 C3 C2 120.25(15) . . ?
F3 C3 C4 120.40(14) . . ?
C2 C3 C4 119.36(15) . . ?
F4 C4 C3 119.47(15) . . ?
F4 C4 C5 119.89(15) . . ?
C5 C4 C3 120.65(15) . . ?
F5 C5 C4 119.96(14) . . ?
F5 C5 C6 120.93(15) . . ?
C4 C5 C6 119.10(15) . . ?
F6 C6 C1 119.32(14) . . ?
F6 C6 C5 119.07(14) . . ?
C5 C6 C1 121.58(15) . . ?
C8 C7 P1 119.26(12) . . ?
C12 C7 P1 123.64(12) . . ?
C12 C7 C8 116.72(14) . . ?
F7 C8 C7 120.37(14) . . ?
F7 C8 C9 117.58(14) . . ?
C9 C8 C7 122.05(15) . . ?
F8 C9 C8 120.11(15) . . ?
F8 C9 C10 120.09(15) . . ?
C8 C9 C10 119.80(15) . . ?
F9 C10 C9 120.04(15) . . ?
F9 C10 C11 120.17(15) . . ?
C9 C10 C11 119.79(15) . . ?
F10 C11 C10 120.18(15) . . ?
F10 C11 C12 120.14(15) . . ?
C12 C11 C10 119.68(15) . . ?
F11 C12 C7 120.94(14) . . ?
F11 C12 C11 117.05(14) . . ?
C11 C12 C7 121.94(15) . . ?
C14 C13 P1 120.51(12) . . ?
C18 C13 P1 121.85(12) . . ?
C18 C13 C14 117.15(14) . . ?
F12 C14 C13 120.54(14) . . ?
F12 C14 C15 117.89(15) . . ?
C15 C14 C13 121.57(15) . . ?
F13 C15 C14 120.41(16) . . ?
F13 C15 C16 120.09(15) . . ?
C14 C15 C16 119.48(16) . . ?
F14 C16 C15 119.43(17) . . ?
F14 C16 C17 120.12(17) . . ?
C17 C16 C15 120.45(15) . . ?
F15 C17 C16 120.44(15) . . ?
F15 C17 C18 120.32(16) . . ?
C16 C17 C18 119.24(16) . . ?
F16 C18 C13 119.82(14) . . ?
F16 C18 C17 118.09(15) . . ?
C17 C18 C13 122.08(15) . . ?
O1 C19 H19 121.3(12) . . ?
N00Q C19 O1 120.13(14) . . ?
N00Q C19 H19 118.5(12) . . ?
N00Q C20 H20A 109.5 . . ?
N00Q C20 H20B 109.5 . . ?
N00Q C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
N00Q C21 H21A 109.5 . . ?
N00Q C21 H21B 109.5 . . ?
N00Q C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
O2 S1 O3 114.77(9) . . ?
O2 S1 C22 103.21(9) . . ?
O3 S1 C22 102.55(9) . . ?
O4 S1 O2 115.38(9) . . ?
O4 S1 O3 114.94(10) . . ?
O4 S1 C22 103.49(9) . . ?
F17 C22 S1 111.25(13) . . ?
F18 C22 S1 111.35(13) . . ?
F18 C22 F17 107.59(17) . . ?
F19 C22 S1 111.43(14) . . ?
F19 C22 F17 107.37(16) . . ?
F19 C22 F18 107.66(16) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
P1 O1 C19 N00Q 170.90(11) . . . . ?
P1 C1 C2 F2 3.2(2) . . . . ?
P1 C1 C2 C3 -178.06(12) . . . . ?
P1 C1 C6 F6 -1.6(2) . . . . ?
P1 C1 C6 C5 176.38(12) . . . . ?
P1 C7 C8 F7 8.3(2) . . . . ?
P1 C7 C8 C9 -171.73(12) . . . . ?
P1 C7 C12 F11 -5.1(2) . . . . ?
P1 C7 C12 C11 171.77(12) . . . . ?
P1 C13 C14 F12 8.2(2) . . . . ?
P1 C13 C14 C15 -172.30(13) . . . . ?
P1 C13 C18 F16 -7.6(2) . . . . ?
P1 C13 C18 C17 170.95(12) . . . . ?
F1 P1 C1 C2 61.39(12) . . . . ?
F1 P1 C1 C6 -115.56(13) . . . . ?
F1 P1 C7 C8 49.16(13) . . . . ?
F1 P1 C7 C12 -123.60(13) . . . . ?
F1 P1 C13 C14 49.20(13) . . . . ?
F1 P1 C13 C18 -122.53(13) . . . . ?
F2 C2 C3 F3 0.6(2) . . . . ?
F2 C2 C3 C4 -179.62(14) . . . . ?
F3 C3 C4 F4 -1.4(2) . . . . ?
F3 C3 C4 C5 179.13(14) . . . . ?
F4 C4 C5 F5 -1.0(2) . . . . ?
F4 C4 C5 C6 179.67(14) . . . . ?
F5 C5 C6 F6 0.2(2) . . . . ?
F5 C5 C6 C1 -177.80(14) . . . . ?
F7 C8 C9 F8 -1.2(2) . . . . ?
F7 C8 C9 C10 178.91(14) . . . . ?
F8 C9 C10 F9 1.0(2) . . . . ?
F8 C9 C10 C11 -179.76(15) . . . . ?
F9 C10 C11 F10 -0.5(2) . . . . ?
F9 C10 C11 C12 179.48(15) . . . . ?
F10 C11 C12 F11 -2.7(2) . . . . ?
F10 C11 C12 C7 -179.68(14) . . . . ?
F12 C14 C15 F13 0.0(2) . . . . ?
F12 C14 C15 C16 -178.76(14) . . . . ?
F13 C15 C16 F14 -0.4(3) . . . . ?
F13 C15 C16 C17 179.22(15) . . . . ?
F14 C16 C17 F15 1.1(2) . . . . ?
F14 C16 C17 C18 -179.56(15) . . . . ?
F15 C17 C18 F16 -1.3(2) . . . . ?
F15 C17 C18 C13 -179.90(14) . . . . ?
O1 P1 C1 C2 -114.73(13) . . . . ?
O1 P1 C1 C6 68.32(13) . . . . ?
O1 P1 C7 C8 -134.91(13) . . . . ?
O1 P1 C7 C12 52.33(13) . . . . ?
O1 P1 C13 C14 -130.78(13) . . . . ?
O1 P1 C13 C18 57.50(13) . . . . ?
C1 P1 O1 C19 -100.35(14) . . . . ?
C1 P1 C7 C8 138.73(12) . . . . ?
C1 P1 C7 C12 -34.03(16) . . . . ?
C1 P1 C13 C14 -40.15(16) . . . . ?
C1 P1 C13 C18 148.12(12) . . . . ?
C1 C2 C3 F3 -178.17(14) . . . . ?
C1 C2 C3 C4 1.6(2) . . . . ?
C2 C1 C6 F6 -178.60(13) . . . . ?
C2 C1 C6 C5 -0.6(2) . . . . ?
C2 C3 C4 F4 178.76(14) . . . . ?
C2 C3 C4 C5 -0.7(2) . . . . ?
C3 C4 C5 F5 178.49(14) . . . . ?
C3 C4 C5 C6 -0.9(2) . . . . ?
C4 C5 C6 F6 179.53(14) . . . . ?
C4 C5 C6 C1 1.6(2) . . . . ?
C6 C1 C2 F2 -179.69(13) . . . . ?
C6 C1 C2 C3 -1.0(2) . . . . ?
C7 P1 O1 C19 140.92(14) . . . . ?
C7 P1 C1 C2 -28.77(15) . . . . ?
C7 P1 C1 C6 154.28(12) . . . . ?
C7 P1 C13 C14 139.70(13) . . . . ?
C7 P1 C13 C18 -32.03(16) . . . . ?
C7 C8 C9 F8 178.84(14) . . . . ?
C7 C8 C9 C10 -1.0(2) . . . . ?
C8 C7 C12 F11 -177.98(13) . . . . ?
C8 C7 C12 C11 -1.2(2) . . . . ?
C8 C9 C10 F9 -179.12(15) . . . . ?
C8 C9 C10 C11 0.1(2) . . . . ?
C9 C10 C11 F10 -179.78(15) . . . . ?
C9 C10 C11 C12 0.2(2) . . . . ?
C10 C11 C12 F11 177.25(14) . . . . ?
C10 C11 C12 C7 0.3(2) . . . . ?
C12 C7 C8 F7 -178.42(13) . . . . ?
C12 C7 C8 C9 1.5(2) . . . . ?
C13 P1 O1 C19 22.29(14) . . . . ?
C13 P1 C1 C2 151.08(12) . . . . ?
C13 P1 C1 C6 -25.87(16) . . . . ?
C13 P1 C7 C8 -41.12(15) . . . . ?
C13 P1 C7 C12 146.12(13) . . . . ?
C13 C14 C15 F13 -179.54(14) . . . . ?
C13 C14 C15 C16 1.7(3) . . . . ?
C14 C13 C18 F16 -179.61(13) . . . . ?
C14 C13 C18 C17 -1.0(2) . . . . ?
C14 C15 C16 F14 178.36(15) . . . . ?
C14 C15 C16 C17 -2.0(3) . . . . ?
C15 C16 C17 F15 -178.54(15) . . . . ?
C15 C16 C17 C18 0.8(3) . . . . ?
C16 C17 C18 F16 179.32(14) . . . . ?
C16 C17 C18 C13 0.7(2) . . . . ?
C18 C13 C14 F12 -179.71(14) . . . . ?
C18 C13 C14 C15 -0.2(2) . . . . ?
C20 N00Q C19 O1 177.58(14) . . . . ?
C21 N00Q C19 O1 -4.5(2) . . . . ?
O2 S1 C22 F17 -55.20(16) . . . . ?
O2 S1 C22 F18 -175.20(14) . . . . ?
O2 S1 C22 F19 64.58(15) . . . . ?
O3 S1 C22 F17 64.34(15) . . . . ?
O3 S1 C22 F18 -55.66(16) . . . . ?
O3 S1 C22 F19 -175.88(14) . . . . ?
O4 S1 C22 F17 -175.81(14) . . . . ?
O4 S1 C22 F18 64.19(16) . . . . ?
O4 S1 C22 F19 -56.03(16) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.455
_oxdiff_exptl_absorpt_empirical_full_min 0.698
####################################################################### 
# 
# 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_24c
_database_code_depnum_ccdc_archive 'CCDC 2051054'
loop_
_audit_author_name
_audit_author_address
'Felix Hennersdorf'
;TU Dresden
Germany
;
_audit_update_record             
;
2020-12-21 deposited with the CCDC.	2021-04-01 downloaded from the CCDC.
;
_audit_creation_date             2020-12-21
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H10 F N O4 S2'
_chemical_formula_sum            'C12 H10 F N O4 S2'
_chemical_formula_weight         315.33
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C12 H9 F N O4 S2'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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           15
_space_group_name_H-M_alt        'I 1 2/a 1'
_space_group_name_Hall           '-I 2ya'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'x, -y+1/2, z+1/2'

_cell_length_a                   7.56523(13)
_cell_length_b                   13.96865(19)
_cell_length_c                   24.4631(3)
_cell_angle_alpha                90
_cell_angle_beta                 93.8142(13)
_cell_angle_gamma                90
_cell_volume                     2579.44(7)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    4225
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      76.1230
_cell_measurement_theta_min      3.6130
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    4.005
_exptl_absorpt_correction_T_max  0.977
_exptl_absorpt_correction_T_min  0.965
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.624
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1296
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
4 -1 5 0.0433
2 -8 -5 0.0324
0 8 8 0.0308
-4 1 -5 0.0199
-1 -8 7 0.0285
2 -3 -14 0.0293
1 5 -12 0.0579
2 -5 11 0.0354

_exptl_crystal_size_max          0.125
_exptl_crystal_size_mid          0.075
_exptl_crystal_size_min          0.063
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
4.0008 -1.0105 4.9980 -0.8929 -0.0849 0.0905
2.0045 -8.0022 -4.9952 -0.2578 -0.0695 0.9787
-0.0044 7.9968 7.9939 -0.2012 0.0289 -0.9957
-4.0008 1.0105 -4.9980 0.8929 0.0849 -0.0905
-0.9989 -7.9940 6.9963 0.0325 -0.8466 0.5331
2.0046 -3.0043 -13.9902 -0.0457 0.6596 0.7561
1.0010 4.9952 -11.9928 0.0912 0.9373 -0.1026
2.0003 -5.0034 10.9942 -0.6471 -0.7189 0.2341

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0199
_diffrn_reflns_av_unetI/netI     0.0244
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            6394
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.642
_diffrn_reflns_theta_min         3.622
_diffrn_ambient_temperature      100
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2850
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -53.00  34.00   0.50    2.00    --  -38.50  38.00 -30.00  174
  2  ω    -61.00 -10.00   0.50    2.00    --  -38.50 125.00  30.00  102
  3  ω   -111.00 -24.00   0.50    2.00    --  -38.50 -77.00-150.00  174
  4  ω     58.00 116.00   0.50    8.00    --  111.00 -61.00-120.00  116
  5  ω     85.00 125.00   0.50    8.00    --  111.00 -30.00-150.00   80
  6  ω     88.00 169.00   0.50    8.00    --  111.00  45.00-180.00  162
  7  ω    125.00 154.00   0.50    8.00    --  111.00  77.00-120.00   58
  8  ω     80.00 120.00   0.50    8.00    --  111.00  77.00-120.00   80
  9  ω     38.00 135.00   0.50    8.00    --  111.00 -30.00   0.00  194
 10  ω     41.00  90.00   0.50    8.00    --  111.00 -30.00 150.00   98
 11  ω     40.00 142.00   0.50    8.00    --  111.00 -77.00  30.00  204
 12  ω     41.00 118.00   0.50    8.00    --  111.00-125.00 -30.00  154
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1932458000
_diffrn_orient_matrix_UB_12      -0.0010866000
_diffrn_orient_matrix_UB_13      -0.0241895000
_diffrn_orient_matrix_UB_21      0.0560120000
_diffrn_orient_matrix_UB_22      0.0544334000
_diffrn_orient_matrix_UB_23      -0.0508099000
_diffrn_orient_matrix_UB_31      0.0340602000
_diffrn_orient_matrix_UB_32      -0.0959420000
_diffrn_orient_matrix_UB_33      -0.0285625000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2585
_reflns_number_total             2677
_reflns_odcompleteness_completeness 99.75
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_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 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_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         0.415
_refine_diff_density_min         -0.371
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     194
_refine_ls_number_reflns         2677
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0311
_refine_ls_R_factor_gt           0.0300
_refine_ls_restrained_S_all      1.084
_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)+(0.0327P)²+3.0859P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0750
_refine_ls_wR_factor_ref         0.0760
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Others
 Sof(F1B)=Sof(H4)=1-FVAR(1)
 Sof(F1A)=Sof(H10)=FVAR(1)
3.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C8(H8), C9(H9), C10(H10), C11(H11),
 C12(H12)
;
_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
S1 S 0.32635(5) 0.64949(3) 0.67492(2) 0.01810(11) Uani 1 1 d . . . . .
S2 S 0.60076(5) 0.61890(3) 0.59715(2) 0.01667(11) Uani 1 1 d . . . . .
F1A F 0.66870(18) 0.50751(10) 0.87872(5) 0.0336(4) Uani 0.869(4) 1 d . . P A 1
F1B F 0.4004(15) 0.9021(6) 0.4329(3) 0.041(3) Uani 0.131(4) 1 d . . P A 2
O1 O 0.14668(16) 0.61760(9) 0.67164(5) 0.0245(3) Uani 1 1 d . . . . .
O2 O 0.36505(17) 0.74908(8) 0.67009(5) 0.0254(3) Uani 1 1 d . . . . .
O3 O 0.71376(15) 0.66008(9) 0.63992(5) 0.0230(2) Uani 1 1 d . . . . .
O4 O 0.65384(16) 0.53321(8) 0.57001(5) 0.0229(2) Uani 1 1 d . . . . .
N1 N 0.41439(18) 0.59054(10) 0.62430(5) 0.0187(3) Uani 1 1 d . . . . .
C1 C 0.4366(2) 0.60548(11) 0.73524(6) 0.0179(3) Uani 1 1 d . . . . .
C2 C 0.4334(2) 0.50761(11) 0.74567(6) 0.0195(3) Uani 1 1 d . . . . .
H2 H 0.377337 0.464746 0.719818 0.023 Uiso 1 1 calc R . . . .
C3 C 0.5137(2) 0.47381(12) 0.79459(7) 0.0227(3) Uani 1 1 d . . . . .
H3 H 0.516041 0.407287 0.802676 0.027 Uiso 1 1 calc R . . . .
C4 C 0.5901(2) 0.53945(14) 0.83120(7) 0.0254(3) Uani 1 1 d . . . . .
H4 H 0.643954 0.516349 0.864840 0.031 Uiso 0.131(4) 1 calc R . P A 2
C5 C 0.5925(2) 0.63637(13) 0.82159(7) 0.0271(4) Uani 1 1 d . . . . .
H5 H 0.645537 0.679092 0.848077 0.032 Uiso 1 1 calc R . . . .
C6 C 0.5155(2) 0.67036(12) 0.77229(7) 0.0239(3) Uani 1 1 d . . . . .
H6 H 0.516657 0.736804 0.764056 0.029 Uiso 1 1 calc R . . . .
C7 C 0.5459(2) 0.70483(11) 0.54645(6) 0.0176(3) Uani 1 1 d . . . . .
C8 C 0.5443(3) 0.80077(12) 0.56082(7) 0.0260(4) Uani 1 1 d . . . . .
H8 H 0.574129 0.820134 0.597513 0.031 Uiso 1 1 calc R . . . .
C9 C 0.4986(3) 0.86780(13) 0.52074(8) 0.0353(4) Uani 1 1 d . . . . .
H9 H 0.496768 0.933919 0.529775 0.042 Uiso 1 1 calc R . . . .
C10 C 0.4554(3) 0.83834(14) 0.46717(7) 0.0311(4) Uani 1 1 d . . . . .
H10 H 0.423727 0.884666 0.439816 0.037 Uiso 0.869(4) 1 calc R . P A 1
C11 C 0.4579(2) 0.74271(13) 0.45333(6) 0.0247(3) Uani 1 1 d . . . . .
H11 H 0.428897 0.723500 0.416576 0.030 Uiso 1 1 calc R . . . .
C12 C 0.5029(2) 0.67447(12) 0.49312(6) 0.0209(3) Uani 1 1 d . . . . .
H12 H 0.504203 0.608351 0.484063 0.025 Uiso 1 1 calc R . . . .
H1 H 0.349(3) 0.5532(16) 0.6087(9) 0.025 Uiso 1 1 d 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 1.4276(13) . ?
S1 O2 1.4281(12) . ?
S1 N1 1.6629(13) . ?
S1 C1 1.7572(16) . ?
S2 O3 1.4273(12) . ?
S2 O4 1.4388(12) . ?
S2 N1 1.6464(14) . ?
S2 C7 1.7557(15) . ?
F1A C4 1.346(2) . ?
F1B C10 1.274(8) . ?
N1 H1 0.80(2) . ?
C1 C2 1.391(2) . ?
C1 C6 1.388(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.388(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.381(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.374(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.388(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.386(2) . ?
C7 C12 1.390(2) . ?
C8 H8 0.9500 . ?
C8 C9 1.383(2) . ?
C9 H9 0.9500 . ?
C9 C10 1.392(3) . ?
C10 H10 0.9500 . ?
C10 C11 1.378(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.388(2) . ?
C12 H12 0.9500 . ?

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 O2 119.93(8) . . ?
O1 S1 N1 103.33(7) . . ?
O1 S1 C1 109.58(7) . . ?
O2 S1 N1 109.04(7) . . ?
O2 S1 C1 108.77(7) . . ?
N1 S1 C1 105.12(7) . . ?
O3 S2 O4 120.10(7) . . ?
O3 S2 N1 106.77(7) . . ?
O3 S2 C7 110.14(7) . . ?
O4 S2 N1 104.99(7) . . ?
O4 S2 C7 107.64(7) . . ?
N1 S2 C7 106.31(7) . . ?
S1 N1 H1 114.2(16) . . ?
S2 N1 S1 125.27(9) . . ?
S2 N1 H1 119.1(15) . . ?
C2 C1 S1 118.98(12) . . ?
C6 C1 S1 118.64(12) . . ?
C6 C1 C2 122.28(15) . . ?
C1 C2 H2 120.7 . . ?
C3 C2 C1 118.69(15) . . ?
C3 C2 H2 120.7 . . ?
C2 C3 H3 120.9 . . ?
C4 C3 C2 118.26(15) . . ?
C4 C3 H3 120.9 . . ?
F1A C4 C3 118.80(16) . . ?
F1A C4 C5 117.66(16) . . ?
C3 C4 H4 118.2 . . ?
C5 C4 C3 123.54(16) . . ?
C5 C4 H4 118.2 . . ?
C4 C5 H5 120.8 . . ?
C4 C5 C6 118.44(16) . . ?
C6 C5 H5 120.8 . . ?
C1 C6 H6 120.6 . . ?
C5 C6 C1 118.78(16) . . ?
C5 C6 H6 120.6 . . ?
C8 C7 S2 119.18(12) . . ?
C8 C7 C12 121.86(14) . . ?
C12 C7 S2 118.96(12) . . ?
C7 C8 H8 120.6 . . ?
C9 C8 C7 118.74(15) . . ?
C9 C8 H8 120.6 . . ?
C8 C9 H9 120.0 . . ?
C8 C9 C10 119.97(17) . . ?
C10 C9 H9 120.0 . . ?
F1B C10 C9 117.3(5) . . ?
F1B C10 C11 121.7(5) . . ?
C9 C10 H10 119.6 . . ?
C11 C10 C9 120.76(16) . . ?
C11 C10 H10 119.6 . . ?
C10 C11 H11 120.0 . . ?
C10 C11 C12 120.00(15) . . ?
C12 C11 H11 120.0 . . ?
C7 C12 H12 120.7 . . ?
C11 C12 C7 118.67(15) . . ?
C11 C12 H12 120.7 . . ?

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
S1 C1 C2 C3 -177.03(12) . . . . ?
S1 C1 C6 C5 175.79(13) . . . . ?
S2 C7 C8 C9 -179.15(15) . . . . ?
S2 C7 C12 C11 179.38(12) . . . . ?
F1A C4 C5 C6 178.61(15) . . . . ?
F1B C10 C11 C12 -174.0(6) . . . . ?
O1 S1 N1 S2 162.34(10) . . . . ?
O1 S1 C1 C2 53.77(14) . . . . ?
O1 S1 C1 C6 -122.63(13) . . . . ?
O2 S1 N1 S2 33.71(12) . . . . ?
O2 S1 C1 C2 -173.36(12) . . . . ?
O2 S1 C1 C6 10.24(15) . . . . ?
O3 S2 N1 S1 32.12(12) . . . . ?
O3 S2 C7 C8 -27.24(16) . . . . ?
O3 S2 C7 C12 153.60(12) . . . . ?
O4 S2 N1 S1 160.66(9) . . . . ?
O4 S2 C7 C8 -159.86(13) . . . . ?
O4 S2 C7 C12 20.98(15) . . . . ?
N1 S1 C1 C2 -56.70(14) . . . . ?
N1 S1 C1 C6 126.90(13) . . . . ?
N1 S2 C7 C8 88.06(14) . . . . ?
N1 S2 C7 C12 -91.10(13) . . . . ?
C1 S1 N1 S2 -82.77(11) . . . . ?
C1 C2 C3 C4 1.3(2) . . . . ?
C2 C1 C6 C5 -0.5(2) . . . . ?
C2 C3 C4 F1A -179.86(15) . . . . ?
C2 C3 C4 C5 -0.7(3) . . . . ?
C3 C4 C5 C6 -0.6(3) . . . . ?
C4 C5 C6 C1 1.2(3) . . . . ?
C6 C1 C2 C3 -0.8(2) . . . . ?
C7 S2 N1 S1 -85.44(11) . . . . ?
C7 C8 C9 C10 0.0(3) . . . . ?
C8 C7 C12 C11 0.2(2) . . . . ?
C8 C9 C10 F1B 174.4(6) . . . . ?
C8 C9 C10 C11 -0.2(3) . . . . ?
C9 C10 C11 C12 0.4(3) . . . . ?
C10 C11 C12 C7 -0.4(3) . . . . ?
C12 C7 C8 C9 0.0(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.525
_oxdiff_exptl_absorpt_empirical_full_min 0.846
