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

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
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data_170411_mfh_451_173_3_sq
_database_code_depnum_ccdc_archive 'CCDC 1563770'
_audit_update_record             
;
2017-07-21 deposited with the CCDC.
2017-12-12 downloaded from the CCDC.
;
_audit_creation_date             2017-04-11
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H17 Cl N2 O3 S2'
_chemical_formula_sum            'C23 H17 Cl N2 O3 S2'
_chemical_formula_weight         468.95
_chemical_melting_point          ?
_chemical_oxdiff_formula         'c10 h10 n2 o8 S1 CL1'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      trigonal
_space_group_IT_number           148
_space_group_name_H-M_alt        'R -3'
_space_group_name_Hall           '-R 3'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'

_cell_length_a                   31.8220(18)
_cell_length_b                   31.8220(18)
_cell_length_c                   13.3046(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     11667.7(14)
_cell_formula_units_Z            18
_cell_measurement_reflns_used    7060
_cell_measurement_temperature    170.1
_cell_measurement_theta_max      29.3013
_cell_measurement_theta_min      3.3232
_shelx_estimated_absorpt_T_max   0.907
_shelx_estimated_absorpt_T_min   0.857
_exptl_absorpt_coefficient_mu    0.332
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80412
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
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    1.201
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             4356
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.3
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0550
_diffrn_reflns_av_unetI/netI     0.0784
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       37
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       36
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            8077
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.348
_diffrn_reflns_theta_min         3.330
_diffrn_ambient_temperature      170.1
_diffrn_detector_area_resol_mean 5.1796
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -39.00   53.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.6246   35.0000 -155.0000 92
;
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0221289000
_diffrn_orient_matrix_UB_12      -0.0207242000
_diffrn_orient_matrix_UB_13      0.0144058000
_diffrn_orient_matrix_UB_21      -0.0130756000
_diffrn_orient_matrix_UB_22      0.0108687000
_diffrn_orient_matrix_UB_23      -0.0193720000
_diffrn_orient_matrix_UB_31      -0.0013481000
_diffrn_orient_matrix_UB_32      -0.0107036000
_diffrn_orient_matrix_UB_33      -0.0475300000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3650
_reflns_number_total             4730
_reflns_odcompleteness_completeness 99.53
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         0.302
_refine_diff_density_min         -0.523
_refine_diff_density_rms         0.058
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     281
_refine_ls_number_reflns         4730
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0660
_refine_ls_R_factor_gt           0.0515
_refine_ls_restrained_S_all      1.024
_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)+(0.0557P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1215
_refine_ls_wR_factor_ref         0.1335
_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:
 C15(H15A,H15B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C10(H10), C11(H11), C12(H12), C13(H13),
 C19(H19), C20(H20), C22(H22), C23(H23)
2.c Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C)
;
_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
Cl1 Cl 0.38489(3) 0.10628(4) 0.90051(5) 0.0623(3) Uani 1 1 d . . . . .
S1 S 0.40179(2) -0.05733(2) 0.83421(4) 0.03352(19) Uani 1 1 d . . . . .
S2 S 0.43180(2) 0.00759(2) 0.55062(4) 0.02888(19) Uani 1 1 d . . . . .
O1 O 0.51199(6) 0.02508(6) 0.68321(11) 0.0321(4) Uani 1 1 d . . . . .
O2 O 0.47553(7) 0.04138(6) 0.50196(11) 0.0373(4) Uani 1 1 d . . . . .
O3 O 0.38848(7) -0.02131(7) 0.49394(12) 0.0400(5) Uani 1 1 d . . . . .
N1 N 0.38019(7) -0.11597(7) 0.56446(14) 0.0276(5) Uani 1 1 d . . . . .
N2 N 0.44192(7) -0.03373(7) 0.60939(13) 0.0262(4) Uani 1 1 d . . . . .
C1 C 0.31938(9) -0.18189(10) 0.7866(2) 0.0396(7) Uani 1 1 d . . . . .
H1 H 0.319412 -0.174816 0.856030 0.048 Uiso 1 1 calc R . . . .
C2 C 0.29132(10) -0.22828(10) 0.7518(2) 0.0466(7) Uani 1 1 d . . . . .
H2 H 0.272835 -0.253592 0.798231 0.056 Uiso 1 1 calc R . . . .
C3 C 0.28918(10) -0.23938(10) 0.6490(2) 0.0453(7) Uani 1 1 d . . . . .
H3 H 0.268762 -0.271800 0.626925 0.054 Uiso 1 1 calc R . . . .
C4 C 0.31639(9) -0.20372(10) 0.5798(2) 0.0390(7) Uani 1 1 d . . . . .
H4 H 0.314602 -0.210905 0.510070 0.047 Uiso 1 1 calc R . . . .
C5 C 0.34651(9) -0.15696(9) 0.61531(17) 0.0307(6) Uani 1 1 d . . . . .
C6 C 0.34794(8) -0.14514(9) 0.71871(18) 0.0313(6) Uani 1 1 d . . . . .
C7 C 0.38328(8) -0.09463(9) 0.72776(17) 0.0290(6) Uani 1 1 d . . . . .
C8 C 0.40154(8) -0.07890(9) 0.63323(16) 0.0263(5) Uani 1 1 d . . . . .
C9 C 0.45053(9) -0.06282(9) 0.88523(16) 0.0301(6) Uani 1 1 d . . . . .
C10 C 0.45174(10) -0.06416(10) 0.99055(17) 0.0380(6) Uani 1 1 d . . . . .
H10 H 0.426080 -0.065033 1.028691 0.046 Uiso 1 1 calc R . . . .
C11 C 0.49013(11) -0.06420(11) 1.03901(19) 0.0469(7) Uani 1 1 d . . . . .
H11 H 0.491212 -0.064070 1.110368 0.056 Uiso 1 1 calc R . . . .
C12 C 0.52665(11) -0.06444(11) 0.98484(19) 0.0458(7) Uani 1 1 d . . . . .
H12 H 0.552398 -0.065604 1.018404 0.055 Uiso 1 1 calc R . . . .
C13 C 0.52576(9) -0.06294(9) 0.87980(17) 0.0349(6) Uani 1 1 d . . . . .
H13 H 0.551060 -0.063195 0.842395 0.042 Uiso 1 1 calc R . . . .
C14 C 0.48849(9) -0.06109(8) 0.82922(15) 0.0268(5) Uani 1 1 d . . . . .
C15 C 0.49170(9) -0.05723(9) 0.71462(16) 0.0270(5) Uani 1 1 d . . . . .
H15A H 0.524085 -0.051182 0.693468 0.032 Uiso 1 1 calc R . . . .
H15B H 0.467193 -0.088734 0.685615 0.032 Uiso 1 1 calc R . . . .
C16 C 0.48378(8) -0.01762(9) 0.67149(16) 0.0257(5) Uani 1 1 d . . . . .
C17 C 0.39187(10) -0.11392(10) 0.45787(16) 0.0358(6) Uani 1 1 d . . . . .
H17A H 0.367883 -0.110373 0.418167 0.054 Uiso 1 1 calc GR . . . .
H17B H 0.391306 -0.143896 0.438380 0.054 Uiso 1 1 calc GR . . . .
H17C H 0.424256 -0.086116 0.445461 0.054 Uiso 1 1 calc GR . . . .
C18 C 0.41862(9) 0.03628(8) 0.64745(15) 0.0256(5) Uani 1 1 d . . . . .
C19 C 0.45575(9) 0.07845(9) 0.68885(16) 0.0311(6) Uani 1 1 d . . . . .
H19 H 0.487905 0.092377 0.663628 0.037 Uiso 1 1 calc R . . . .
C20 C 0.44505(10) 0.10004(10) 0.76817(17) 0.0358(6) Uani 1 1 d . . . . .
H20 H 0.469842 0.128993 0.798057 0.043 Uiso 1 1 calc R . . . .
C21 C 0.39802(10) 0.07887(10) 0.80276(17) 0.0352(6) Uani 1 1 d . . . . .
C22 C 0.36089(10) 0.03688(10) 0.76161(18) 0.0360(6) Uani 1 1 d . . . . .
H22 H 0.328784 0.023016 0.787068 0.043 Uiso 1 1 calc R . . . .
C23 C 0.37134(9) 0.01533(9) 0.68242(18) 0.0332(6) Uani 1 1 d . . . . .
H23 H 0.346388 -0.013490 0.652421 0.040 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
Cl1 C21 1.730(2) . ?
S1 C7 1.750(2) . ?
S1 C9 1.780(2) . ?
S2 O2 1.4195(18) . ?
S2 O3 1.4309(18) . ?
S2 N2 1.693(2) . ?
S2 C18 1.747(2) . ?
O1 C16 1.207(3) . ?
N1 C5 1.382(3) . ?
N1 C8 1.374(3) . ?
N1 C17 1.459(3) . ?
N2 C8 1.404(3) . ?
N2 C16 1.427(3) . ?
C1 H1 0.9500 . ?
C1 C2 1.369(4) . ?
C1 C6 1.396(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.406(4) . ?
C3 H3 0.9500 . ?
C3 C4 1.379(4) . ?
C4 H4 0.9500 . ?
C4 C5 1.389(3) . ?
C5 C6 1.421(3) . ?
C6 C7 1.434(3) . ?
C7 C8 1.371(3) . ?
C9 C10 1.403(3) . ?
C9 C14 1.397(3) . ?
C10 H10 0.9500 . ?
C10 C11 1.382(4) . ?
C11 H11 0.9500 . ?
C11 C12 1.371(4) . ?
C12 H12 0.9500 . ?
C12 C13 1.399(3) . ?
C13 H13 0.9500 . ?
C13 C14 1.390(3) . ?
C14 C15 1.529(3) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C16 1.516(3) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 C19 1.384(3) . ?
C18 C23 1.386(3) . ?
C19 H19 0.9500 . ?
C19 C20 1.391(3) . ?
C20 H20 0.9500 . ?
C20 C21 1.377(4) . ?
C21 C22 1.379(4) . ?
C22 H22 0.9500 . ?
C22 C23 1.385(3) . ?
C23 H23 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
C7 S1 C9 104.85(11) . . ?
O2 S2 O3 120.73(10) . . ?
O2 S2 N2 107.70(10) . . ?
O2 S2 C18 109.93(11) . . ?
O3 S2 N2 103.91(10) . . ?
O3 S2 C18 108.57(11) . . ?
N2 S2 C18 104.71(10) . . ?
C5 N1 C17 125.3(2) . . ?
C8 N1 C5 107.54(18) . . ?
C8 N1 C17 127.1(2) . . ?
C8 N2 S2 117.86(16) . . ?
C8 N2 C16 116.70(18) . . ?
C16 N2 S2 119.60(16) . . ?
C2 C1 H1 120.5 . . ?
C2 C1 C6 119.0(2) . . ?
C6 C1 H1 120.5 . . ?
C1 C2 H2 119.2 . . ?
C1 C2 C3 121.6(3) . . ?
C3 C2 H2 119.2 . . ?
C2 C3 H3 119.6 . . ?
C4 C3 C2 120.7(3) . . ?
C4 C3 H3 119.6 . . ?
C3 C4 H4 121.1 . . ?
C3 C4 C5 117.8(2) . . ?
C5 C4 H4 121.1 . . ?
N1 C5 C4 129.7(2) . . ?
N1 C5 C6 108.5(2) . . ?
C4 C5 C6 121.8(2) . . ?
C1 C6 C5 118.9(2) . . ?
C1 C6 C7 134.6(2) . . ?
C5 C6 C7 106.4(2) . . ?
C6 C7 S1 129.62(18) . . ?
C8 C7 S1 123.88(19) . . ?
C8 C7 C6 106.5(2) . . ?
N1 C8 N2 122.34(19) . . ?
C7 C8 N1 111.1(2) . . ?
C7 C8 N2 125.8(2) . . ?
C10 C9 S1 114.99(19) . . ?
C14 C9 S1 124.86(16) . . ?
C14 C9 C10 119.8(2) . . ?
C9 C10 H10 119.9 . . ?
C11 C10 C9 120.3(2) . . ?
C11 C10 H10 119.9 . . ?
C10 C11 H11 119.8 . . ?
C12 C11 C10 120.5(2) . . ?
C12 C11 H11 119.8 . . ?
C11 C12 H12 120.2 . . ?
C11 C12 C13 119.6(3) . . ?
C13 C12 H12 120.2 . . ?
C12 C13 H13 119.4 . . ?
C14 C13 C12 121.1(2) . . ?
C14 C13 H13 119.4 . . ?
C9 C14 C15 123.8(2) . . ?
C13 C14 C9 118.64(19) . . ?
C13 C14 C15 117.5(2) . . ?
C14 C15 H15A 108.7 . . ?
C14 C15 H15B 108.7 . . ?
H15A C15 H15B 107.6 . . ?
C16 C15 C14 114.33(19) . . ?
C16 C15 H15A 108.7 . . ?
C16 C15 H15B 108.7 . . ?
O1 C16 N2 121.0(2) . . ?
O1 C16 C15 123.2(2) . . ?
N2 C16 C15 115.7(2) . . ?
N1 C17 H17A 109.5 . . ?
N1 C17 H17B 109.5 . . ?
N1 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C19 C18 S2 119.25(18) . . ?
C19 C18 C23 121.9(2) . . ?
C23 C18 S2 118.85(19) . . ?
C18 C19 H19 120.7 . . ?
C18 C19 C20 118.7(2) . . ?
C20 C19 H19 120.7 . . ?
C19 C20 H20 120.5 . . ?
C21 C20 C19 119.1(2) . . ?
C21 C20 H20 120.5 . . ?
C20 C21 Cl1 118.8(2) . . ?
C20 C21 C22 122.4(2) . . ?
C22 C21 Cl1 118.8(2) . . ?
C21 C22 H22 120.7 . . ?
C21 C22 C23 118.7(2) . . ?
C23 C22 H22 120.7 . . ?
C18 C23 H23 120.4 . . ?
C22 C23 C18 119.2(2) . . ?
C22 C23 H23 120.4 . . ?

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

data_170113_mfh_451_132_3
_database_code_depnum_ccdc_archive 'CCDC 1563781'
_audit_update_record             
;
2017-07-21 deposited with the CCDC.
2017-12-12 downloaded from the CCDC.
;
_audit_creation_date             2017-01-13
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.01.04 svn.r3372 for OlexSys, GUI svn.r5289)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H19 F N2 O3 S2'
_chemical_formula_sum            'C23 H19 F N2 O3 S2'
_chemical_formula_weight         454.52
_chemical_melting_point          ?
_chemical_oxdiff_formula         'c10 h10 n2 o8 s1 f1'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   14.9465(16)
_cell_length_b                   9.9560(8)
_cell_length_c                   14.9447(12)
_cell_angle_alpha                90.0
_cell_angle_beta                 105.076(10)
_cell_angle_gamma                90.0
_cell_volume                     2147.3(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5872
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.5387
_cell_measurement_theta_min      2.8028
_cell_oxdiff_angle_alpha         90.036(5)
_cell_oxdiff_angle_beta          105.125(5)
_cell_oxdiff_angle_gamma         90.039(5)
_cell_oxdiff_length_a            14.9342(10)
_cell_oxdiff_length_b            9.9581(6)
_cell_oxdiff_length_c            14.9572(8)
_cell_oxdiff_measurement_reflns_used 5633
_cell_oxdiff_volume              2147.3(2)
_shelx_estimated_absorpt_T_max   0.905
_shelx_estimated_absorpt_T_min   0.876
_exptl_absorpt_coefficient_mu    0.284
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90718
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
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    1.403
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             944
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.36
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0434
_diffrn_reflns_av_unetI/netI     0.0391
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            12822
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.348
_diffrn_reflns_theta_min         3.435
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean 5.1796
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -48.00   42.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -12.7965   85.0000   26.0000 90

#__ type_ start__ end____ width___ exp.time_
  2 omega  -87.00   16.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -12.7965  -77.0000  150.0000 103

#__ type_ start__ end____ width___ exp.time_
  3 omega  -45.00   38.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -12.7965   85.0000  -88.0000 83
;
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0394956000
_diffrn_orient_matrix_UB_12      -0.0356027000
_diffrn_orient_matrix_UB_13      0.0051602000
_diffrn_orient_matrix_UB_21      0.0209210000
_diffrn_orient_matrix_UB_22      -0.0614234000
_diffrn_orient_matrix_UB_23      -0.0075468000
_diffrn_orient_matrix_UB_31      0.0205682000
_diffrn_orient_matrix_UB_32      -0.0057389000
_diffrn_orient_matrix_UB_33      0.0482600000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3096
_reflns_number_total             3906
_reflns_odcompleteness_completeness 99.74
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.206
_refine_diff_density_min         -0.290
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     282
_refine_ls_number_reflns         3906
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0580
_refine_ls_R_factor_gt           0.0441
_refine_ls_restrained_S_all      1.058
_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)+(0.0496P)²+0.5528P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1048
_refine_ls_wR_factor_ref         0.1151
_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), C2(H2), C3(H3), C4(H4), C10(H10), C11(H11), C12(H12), C13(H13),
 C14(H14), C18(H18), C19(H19), C21(H21), C22(H22)
2.b Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C23(H23A,H23B,H23C)
;
_atom_sites_solution_hydrogens   geom
_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 0.24480(4) 0.53331(6) 0.10404(4) 0.04621(19) Uani 1 1 d . . . . .
S2 S 0.18282(5) 0.35229(6) -0.16365(4) 0.04936(19) Uani 1 1 d . . . . .
F1 F 0.10287(12) -0.11242(15) 0.03515(12) 0.0820(5) Uani 1 1 d . . . . .
O1 O -0.00375(11) 0.40387(17) -0.15497(12) 0.0608(5) Uani 1 1 d . . . . .
O2 O 0.28020(12) 0.37406(18) -0.13970(14) 0.0684(5) Uani 1 1 d . . . . .
O3 O 0.13329(15) 0.34183(17) -0.25814(11) 0.0695(5) Uani 1 1 d . . . . .
N1 N 0.21814(12) 0.69069(18) -0.14278(12) 0.0413(4) Uani 1 1 d . . . . .
N2 N 0.14162(12) 0.48708(16) -0.11689(11) 0.0387(4) Uani 1 1 d . . . . .
C1 C 0.35886(17) 0.8248(3) 0.06794(19) 0.0584(7) Uani 1 1 d . . . . .
H1 H 0.374973 0.800463 0.130149 0.070 Uiso 1 1 calc R . . . .
C2 C 0.39260(19) 0.9409(3) 0.0388(2) 0.0723(8) Uani 1 1 d . . . . .
H2 H 0.432201 0.995463 0.082073 0.087 Uiso 1 1 calc R . . . .
C3 C 0.36846(19) 0.9781(3) -0.0541(2) 0.0691(8) Uani 1 1 d . . . . .
H3 H 0.392214 1.057290 -0.071522 0.083 Uiso 1 1 calc R . . . .
C4 C 0.31138(16) 0.9022(2) -0.11995(19) 0.0536(6) Uani 1 1 d . . . . .
H4 H 0.295473 0.927896 -0.181879 0.064 Uiso 1 1 calc R . . . .
C5 C 0.27744(14) 0.7844(2) -0.09150(15) 0.0412(5) Uani 1 1 d . . . . .
C6 C 0.29994(14) 0.7447(2) 0.00158(15) 0.0426(5) Uani 1 1 d . . . . .
C7 C 0.25193(14) 0.6215(2) 0.00580(14) 0.0389(5) Uani 1 1 d . . . . .
C8 C 0.20356(14) 0.5936(2) -0.08311(14) 0.0368(5) Uani 1 1 d . . . . .
C9 C 0.34640(15) 0.4330(2) 0.13423(14) 0.0421(5) Uani 1 1 d . . . . .
C10 C 0.35106(18) 0.3408(2) 0.20360(16) 0.0536(6) Uani 1 1 d . . . . .
H10 H 0.303185 0.335929 0.232680 0.064 Uiso 1 1 calc R . . . .
C11 C 0.4257(2) 0.2557(3) 0.23056(18) 0.0667(7) Uani 1 1 d . . . . .
H11 H 0.428061 0.194128 0.277853 0.080 Uiso 1 1 calc R . . . .
C12 C 0.4957(2) 0.2612(3) 0.18850(19) 0.0739(8) Uani 1 1 d . . . . .
H12 H 0.546214 0.203733 0.206560 0.089 Uiso 1 1 calc R . . . .
C13 C 0.4911(2) 0.3521(4) 0.1193(2) 0.0923(11) Uani 1 1 d . . . . .
H13 H 0.538894 0.355684 0.090144 0.111 Uiso 1 1 calc R . . . .
C14 C 0.41711(19) 0.4388(3) 0.09161(19) 0.0709(8) Uani 1 1 d . . . . .
H14 H 0.415300 0.500518 0.044522 0.085 Uiso 1 1 calc R . . . .
C15 C 0.04669(16) 0.4951(2) -0.12212(15) 0.0429(5) Uani 1 1 d . . . . .
C16 C 0.01514(16) 0.6204(2) -0.08521(18) 0.0525(6) Uani 1 1 d . . . . .
H16A H 0.046303 0.629448 -0.020697 0.079 Uiso 1 1 calc GR . . . .
H16B H -0.050553 0.616114 -0.092527 0.079 Uiso 1 1 calc GR . . . .
H16C H 0.029344 0.696169 -0.118640 0.079 Uiso 1 1 calc GR . . . .
C17 C 0.15693(16) 0.2137(2) -0.10353(15) 0.0432(5) Uani 1 1 d . . . . .
C18 C 0.09404(19) 0.1204(2) -0.14874(18) 0.0618(7) Uani 1 1 d . . . . .
H18 H 0.063579 0.132270 -0.210903 0.074 Uiso 1 1 calc R . . . .
C19 C 0.0761(2) 0.0092(3) -0.1021(2) 0.0668(8) Uani 1 1 d . . . . .
H19 H 0.034378 -0.055797 -0.132128 0.080 Uiso 1 1 calc R . . . .
C20 C 0.12061(19) -0.0032(2) -0.01128(19) 0.0560(6) Uani 1 1 d . . . . .
C21 C 0.1826(2) 0.0879(3) 0.03542(18) 0.0630(7) Uani 1 1 d . . . . .
H21 H 0.211483 0.076201 0.097986 0.076 Uiso 1 1 calc R . . . .
C22 C 0.20177(18) 0.1979(2) -0.01165(16) 0.0575(7) Uani 1 1 d . . . . .
H22 H 0.244831 0.261170 0.018526 0.069 Uiso 1 1 calc R . . . .
C23 C 0.18191(18) 0.6939(3) -0.24281(15) 0.0600(7) Uani 1 1 d . . . . .
H23A H 0.232301 0.689101 -0.271519 0.090 Uiso 1 1 calc GR . . . .
H23B H 0.148275 0.775859 -0.260661 0.090 Uiso 1 1 calc GR . . . .
H23C H 0.141205 0.618992 -0.262366 0.090 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 C7 1.739(2) . ?
S1 C9 1.776(2) . ?
S2 O2 1.4221(19) . ?
S2 O3 1.4178(18) . ?
S2 N2 1.7024(17) . ?
S2 C17 1.746(2) . ?
F1 C20 1.354(3) . ?
O1 C15 1.202(3) . ?
N1 C5 1.376(3) . ?
N1 C8 1.372(3) . ?
N1 C23 1.452(3) . ?
N2 C8 1.413(3) . ?
N2 C15 1.403(3) . ?
C1 H1 0.9300 . ?
C1 C2 1.378(4) . ?
C1 C6 1.394(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.392(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.354(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.389(3) . ?
C5 C6 1.401(3) . ?
C6 C7 1.432(3) . ?
C7 C8 1.366(3) . ?
C9 C10 1.374(3) . ?
C9 C14 1.370(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.376(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.355(4) . ?
C12 H12 0.9300 . ?
C12 C13 1.363(4) . ?
C13 H13 0.9300 . ?
C13 C14 1.380(4) . ?
C14 H14 0.9300 . ?
C15 C16 1.491(3) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 C18 1.370(3) . ?
C17 C22 1.372(3) . ?
C18 H18 0.9300 . ?
C18 C19 1.372(4) . ?
C19 H19 0.9300 . ?
C19 C20 1.353(4) . ?
C20 C21 1.354(4) . ?
C21 H21 0.9300 . ?
C21 C22 1.373(3) . ?
C22 H22 0.9300 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 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
C7 S1 C9 105.28(10) . . ?
O2 S2 N2 103.40(10) . . ?
O2 S2 C17 109.90(12) . . ?
O3 S2 O2 119.80(12) . . ?
O3 S2 N2 108.44(10) . . ?
O3 S2 C17 109.05(11) . . ?
N2 S2 C17 105.16(9) . . ?
C5 N1 C23 124.90(18) . . ?
C8 N1 C5 107.79(17) . . ?
C8 N1 C23 127.26(19) . . ?
C8 N2 S2 117.83(14) . . ?
C15 N2 S2 119.37(14) . . ?
C15 N2 C8 122.44(17) . . ?
C2 C1 H1 120.9 . . ?
C2 C1 C6 118.2(3) . . ?
C6 C1 H1 120.9 . . ?
C1 C2 H2 119.4 . . ?
C1 C2 C3 121.2(2) . . ?
C3 C2 H2 119.4 . . ?
C2 C3 H3 119.1 . . ?
C4 C3 C2 121.8(3) . . ?
C4 C3 H3 119.1 . . ?
C3 C4 H4 121.2 . . ?
C3 C4 C5 117.5(2) . . ?
C5 C4 H4 121.2 . . ?
N1 C5 C4 129.6(2) . . ?
N1 C5 C6 108.33(18) . . ?
C4 C5 C6 122.1(2) . . ?
C1 C6 C5 119.3(2) . . ?
C1 C6 C7 133.7(2) . . ?
C5 C6 C7 107.02(19) . . ?
C6 C7 S1 127.77(17) . . ?
C8 C7 S1 125.81(17) . . ?
C8 C7 C6 106.07(18) . . ?
N1 C8 N2 119.88(18) . . ?
C7 C8 N1 110.79(18) . . ?
C7 C8 N2 129.26(19) . . ?
C10 C9 S1 116.16(17) . . ?
C14 C9 S1 124.77(18) . . ?
C14 C9 C10 119.0(2) . . ?
C9 C10 H10 119.6 . . ?
C9 C10 C11 120.8(2) . . ?
C11 C10 H10 119.6 . . ?
C10 C11 H11 119.9 . . ?
C12 C11 C10 120.3(3) . . ?
C12 C11 H11 119.9 . . ?
C11 C12 H12 120.5 . . ?
C11 C12 C13 119.1(3) . . ?
C13 C12 H12 120.5 . . ?
C12 C13 H13 119.2 . . ?
C12 C13 C14 121.6(3) . . ?
C14 C13 H13 119.2 . . ?
C9 C14 C13 119.2(3) . . ?
C9 C14 H14 120.4 . . ?
C13 C14 H14 120.4 . . ?
O1 C15 N2 119.9(2) . . ?
O1 C15 C16 124.1(2) . . ?
N2 C15 C16 116.08(19) . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C18 C17 S2 119.96(18) . . ?
C18 C17 C22 120.7(2) . . ?
C22 C17 S2 119.36(18) . . ?
C17 C18 H18 120.1 . . ?
C17 C18 C19 119.9(2) . . ?
C19 C18 H18 120.1 . . ?
C18 C19 H19 120.9 . . ?
C20 C19 C18 118.3(2) . . ?
C20 C19 H19 120.9 . . ?
F1 C20 C21 118.3(2) . . ?
C19 C20 F1 118.5(2) . . ?
C19 C20 C21 123.2(2) . . ?
C20 C21 H21 120.7 . . ?
C20 C21 C22 118.5(2) . . ?
C22 C21 H21 120.7 . . ?
C17 C22 C21 119.5(2) . . ?
C17 C22 H22 120.3 . . ?
C21 C22 H22 120.3 . . ?
N1 C23 H23A 109.5 . . ?
N1 C23 H23B 109.5 . . ?
N1 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
