# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_3ab
_database_code_depnum_ccdc_archive 'CCDC 1491616'
_audit_update_record             
;
2017-12-29 deposited with the CCDC.
2018-01-23 downloaded from the CCDC.
;
_audit_creation_date             2017-12-27
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C22 H21 N O3 S'
_chemical_formula_sum            'C22 H21 N O3 S'
_chemical_formula_weight         379.46
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H O N 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'
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'

_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_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z'

_cell_length_a                   7.9842(9)
_cell_length_b                   6.081(2)
_cell_length_c                   20.127(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.170(11)
_cell_angle_gamma                90.00
_cell_volume                     961.9(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    835
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      69.1040
_cell_measurement_theta_min      4.4550
_exptl_absorpt_coefficient_mu    1.673
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.29642
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.310
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             400
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0458
_diffrn_reflns_av_unetI/netI     0.0554
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -3
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            3110
_diffrn_reflns_theta_full        67.03
_diffrn_reflns_theta_max         67.03
_diffrn_reflns_theta_min         4.46
_diffrn_ambient_temperature      294(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3031
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega -111.00  -12.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.2955  -57.0000  -60.0000 99

#__ type_ start__ end____ width___ exp.time_
  2 omega -110.00  -25.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.2955  -38.0000   30.0000 85

#__ type_ start__ end____ width___ exp.time_
  3 omega   40.00   80.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       40.2955 -125.0000 -150.0000 40

#__ type_ start__ end____ width___ exp.time_
  4 omega   59.00   86.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      107.1410  -30.0000   90.0000 27

#__ type_ start__ end____ width___ exp.time_
  5 omega  130.00  172.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      107.1410  125.0000  -30.0000 42

#__ type_ start__ end____ width___ exp.time_
  6 omega   46.00   90.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      107.1410  -30.0000 -120.0000 44

#__ type_ start__ end____ width___ exp.time_
  7 omega   94.00  129.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      107.1410  125.0000  -30.0000 35

#__ type_ start__ end____ width___ exp.time_
  8 omega   31.00   67.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      107.1410  -30.0000  -30.0000 36

#__ type_ start__ end____ width___ exp.time_
  9 omega   48.00   80.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      107.1410  -45.0000 -150.0000 32

#__ type_ start__ end____ width___ exp.time_
 10 omega   43.00   70.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      107.1410  -45.0000  -60.0000 27

#__ type_ start__ end____ width___ exp.time_
 11 omega   81.00  177.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      107.1410   30.0000   90.0000 96

#__ type_ start__ end____ width___ exp.time_
 12 omega   50.00   99.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      107.1410  -95.0000   90.0000 49
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.1673978000
_diffrn_orient_matrix_UB_12      -0.1011666000
_diffrn_orient_matrix_UB_13      0.0372329000
_diffrn_orient_matrix_UB_21      0.0471578000
_diffrn_orient_matrix_UB_22      -0.0665619000
_diffrn_orient_matrix_UB_23      -0.0682209000
_diffrn_orient_matrix_UB_31      0.0902011000
_diffrn_orient_matrix_UB_32      0.2226096000
_diffrn_orient_matrix_UB_33      -0.0035301000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                1654
_reflns_number_total             2346
_reflns_odcompleteness_completeness 99.42
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.196
_refine_diff_density_min         -0.216
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.03(5)
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.990
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         2346
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0813
_refine_ls_R_factor_gt           0.0621
_refine_ls_restrained_S_all      0.990
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0926P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1625
_refine_ls_wR_factor_ref         0.1849
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_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:
 C1(H1A,H1B), C4(H4A,H4B)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C8(H8), C10(H10), C11(H11), C13(H13), C14(H14), C17(H17),
 C18(H18), C20(H20), C21(H21)
2.c Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C22(H22A,H22B,H22C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
C1 C 0.1138(8) 0.3500(14) 0.7325(3) 0.091(2) Uani 1 d . . .
H1A H -0.0055 0.3279 0.7345 0.109 Uiso 1 calc . . R
H1B H 0.1815 0.2451 0.7622 0.109 Uiso 1 calc . . R
C2 C 0.1465(7) 0.3305(10) 0.6609(3) 0.0737(16) Uani 1 d . . .
C3 C 0.2405(8) 0.5066(11) 0.6463(3) 0.0739(15) Uani 1 d . . .
C4 C 0.2828(9) 0.6593(12) 0.7061(3) 0.0870(17) Uani 1 d . . .
H4A H 0.4010 0.6461 0.7276 0.104 Uiso 1 calc . . R
H4B H 0.2583 0.8112 0.6933 0.104 Uiso 1 calc . . R
C5 C 0.0967(8) 0.1721(14) 0.6141(3) 0.096(2) Uani 1 d . . .
H5 H 0.0343 0.0518 0.6245 0.115 Uiso 1 calc . . R
C6 C 0.1402(8) 0.1913(12) 0.5498(3) 0.0862(18) Uani 1 d . . .
H6 H 0.1055 0.0837 0.5175 0.103 Uiso 1 calc . . R
C7 C 0.2336(6) 0.3677(9) 0.5342(3) 0.0675(14) Uani 1 d . . .
C8 C 0.2839(7) 0.5279(9) 0.5828(3) 0.0674(14) Uani 1 d . . .
H8 H 0.3464 0.6488 0.5728 0.081 Uiso 1 calc . . R
C9 C 0.2738(6) 0.3899(9) 0.4640(3) 0.0671(13) Uani 1 d . . .
C10 C 0.2277(9) 0.2330(10) 0.4148(4) 0.0879(19) Uani 1 d . . .
H10 H 0.1791 0.1027 0.4264 0.106 Uiso 1 calc . . R
C11 C 0.2510(10) 0.2618(11) 0.3489(4) 0.0884(18) Uani 1 d . . .
H11 H 0.2137 0.1540 0.3169 0.106 Uiso 1 calc . . R
C12 C 0.3277(8) 0.4461(10) 0.3303(3) 0.0729(15) Uani 1 d . . .
C13 C 0.3810(9) 0.6057(13) 0.3782(3) 0.094(2) Uani 1 d . . .
H13 H 0.4349 0.7323 0.3669 0.113 Uiso 1 calc . . R
C14 C 0.3521(9) 0.5730(12) 0.4443(3) 0.090(2) Uani 1 d . . .
H14 H 0.3879 0.6812 0.4763 0.108 Uiso 1 calc . . R
C15 C 0.3993(13) 0.6683(16) 0.2420(4) 0.118(3) Uani 1 d . . .
H15A H 0.3292 0.7833 0.2549 0.177 Uiso 1 calc . . GR
H15B H 0.3897 0.6669 0.1938 0.177 Uiso 1 calc . . GR
H15C H 0.5157 0.6938 0.2625 0.177 Uiso 1 calc . . GR
C16 C 0.3753(8) 0.5340(11) 0.8734(3) 0.0757(15) Uani 1 d . . .
C17 C 0.3678(8) 0.3377(11) 0.9051(3) 0.0765(15) Uani 1 d . . .
H17 H 0.2638 0.2686 0.9048 0.092 Uiso 1 calc . . R
C18 C 0.5172(9) 0.2422(11) 0.9378(3) 0.0776(16) Uani 1 d . . .
H18 H 0.5124 0.1090 0.9601 0.093 Uiso 1 calc . . R
C19 C 0.6734(9) 0.3406(12) 0.9380(3) 0.0822(17) Uani 1 d . . .
C20 C 0.6757(9) 0.5396(13) 0.9062(4) 0.0912(19) Uani 1 d . . .
H20 H 0.7797 0.6089 0.9065 0.109 Uiso 1 calc . . R
C21 C 0.5284(9) 0.6413(13) 0.8735(3) 0.0856(18) Uani 1 d . . .
H21 H 0.5323 0.7767 0.8523 0.103 Uiso 1 calc . . R
C22 C 0.8355(10) 0.2273(19) 0.9709(4) 0.127(4) Uani 1 d . . .
H22A H 0.8079 0.0931 0.9916 0.191 Uiso 1 calc . . GR
H22B H 0.8980 0.3221 1.0046 0.191 Uiso 1 calc . . GR
H22C H 0.9036 0.1946 0.9373 0.191 Uiso 1 calc . . GR
N1 N 0.1664(7) 0.5757(10) 0.7503(3) 0.0854(15) Uani 1 d . . .
O1 O 0.3459(7) 0.4648(9) 0.2638(3) 0.0994(15) Uani 1 d . . .
O2 O 0.0476(6) 0.5672(13) 0.8540(3) 0.122(2) Uani 1 d . . .
O3 O 0.2137(8) 0.8878(9) 0.8273(3) 0.116(2) Uani 1 d . . .
S1 S 0.1886(3) 0.6570(3) 0.82817(9) 0.0934(6) Uani 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 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C1 C2 1.515(10) . ?
C1 N1 1.461(10) . ?
C2 C3 1.369(9) . ?
C2 C5 1.357(10) . ?
C3 C4 1.510(9) . ?
C3 C8 1.389(8) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 N1 1.484(8) . ?
C5 H5 0.9300 . ?
C5 C6 1.401(9) . ?
C6 H6 0.9300 . ?
C6 C7 1.374(8) . ?
C7 C8 1.388(8) . ?
C7 C9 1.509(8) . ?
C8 H8 0.9300 . ?
C9 C10 1.377(9) . ?
C9 C14 1.370(8) . ?
C10 H10 0.9300 . ?
C10 C11 1.383(9) . ?
C11 H11 0.9300 . ?
C11 C12 1.361(10) . ?
C12 C13 1.381(9) . ?
C12 O1 1.376(8) . ?
C13 H13 0.9300 . ?
C13 C14 1.404(9) . ?
C14 H14 0.9300 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C15 O1 1.404(10) . ?
C16 C17 1.360(8) . ?
C16 C21 1.385(9) . ?
C16 S1 1.769(7) . ?
C17 H17 0.9300 . ?
C17 C18 1.384(9) . ?
C18 H18 0.9300 . ?
C18 C19 1.383(9) . ?
C19 C20 1.371(10) . ?
C19 C22 1.512(11) . ?
C20 H20 0.9300 . ?
C20 C21 1.388(10) . ?
C21 H21 0.9300 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
N1 S1 1.624(6) . ?
O2 S1 1.429(6) . ?
O3 S1 1.418(6) . ?

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
H1A C1 H1B 109.2 . . ?
C2 C1 H1A 111.3 . . ?
C2 C1 H1B 111.3 . . ?
N1 C1 H1A 111.3 . . ?
N1 C1 H1B 111.3 . . ?
N1 C1 C2 102.5(5) . . ?
C3 C2 C1 109.6(6) . . ?
C5 C2 C1 129.6(6) . . ?
C5 C2 C3 120.8(6) . . ?
C2 C3 C4 111.4(6) . . ?
C2 C3 C8 120.3(6) . . ?
C8 C3 C4 128.3(6) . . ?
C3 C4 H4A 111.6 . . ?
C3 C4 H4B 111.6 . . ?
H4A C4 H4B 109.4 . . ?
N1 C4 C3 101.0(6) . . ?
N1 C4 H4A 111.6 . . ?
N1 C4 H4B 111.6 . . ?
C2 C5 H5 120.3 . . ?
C2 C5 C6 119.4(6) . . ?
C6 C5 H5 120.3 . . ?
C5 C6 H6 119.7 . . ?
C7 C6 C5 120.6(6) . . ?
C7 C6 H6 119.7 . . ?
C6 C7 C8 119.2(6) . . ?
C6 C7 C9 119.9(5) . . ?
C8 C7 C9 120.9(5) . . ?
C3 C8 H8 120.2 . . ?
C7 C8 C3 119.6(5) . . ?
C7 C8 H8 120.2 . . ?
C10 C9 C7 122.5(5) . . ?
C14 C9 C7 121.8(5) . . ?
C14 C9 C10 115.6(6) . . ?
C9 C10 H10 118.7 . . ?
C9 C10 C11 122.6(6) . . ?
C11 C10 H10 118.7 . . ?
C10 C11 H11 119.6 . . ?
C12 C11 C10 120.7(6) . . ?
C12 C11 H11 119.6 . . ?
C11 C12 C13 119.0(6) . . ?
C11 C12 O1 117.7(6) . . ?
O1 C12 C13 123.3(6) . . ?
C12 C13 H13 120.6 . . ?
C12 C13 C14 118.7(6) . . ?
C14 C13 H13 120.6 . . ?
C9 C14 C13 123.3(6) . . ?
C9 C14 H14 118.3 . . ?
C13 C14 H14 118.3 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O1 C15 H15A 109.5 . . ?
O1 C15 H15B 109.5 . . ?
O1 C15 H15C 109.5 . . ?
C17 C16 C21 121.7(6) . . ?
C17 C16 S1 120.6(5) . . ?
C21 C16 S1 117.7(5) . . ?
C16 C17 H17 120.5 . . ?
C16 C17 C18 119.1(6) . . ?
C18 C17 H17 120.5 . . ?
C17 C18 H18 119.3 . . ?
C19 C18 C17 121.4(6) . . ?
C19 C18 H18 119.3 . . ?
C18 C19 C22 120.4(7) . . ?
C20 C19 C18 117.9(6) . . ?
C20 C19 C22 121.7(7) . . ?
C19 C20 H20 118.8 . . ?
C19 C20 C21 122.3(7) . . ?
C21 C20 H20 118.8 . . ?
C16 C21 C20 117.7(6) . . ?
C16 C21 H21 121.2 . . ?
C20 C21 H21 121.2 . . ?
C19 C22 H22A 109.5 . . ?
C19 C22 H22B 109.5 . . ?
C19 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C1 N1 C4 111.0(6) . . ?
C1 N1 S1 120.0(4) . . ?
C4 N1 S1 120.1(5) . . ?
C12 O1 C15 117.8(5) . . ?
N1 S1 C16 107.8(3) . . ?
O2 S1 C16 107.3(3) . . ?
O2 S1 N1 106.0(4) . . ?
O3 S1 C16 108.4(4) . . ?
O3 S1 N1 106.4(3) . . ?
O3 S1 O2 120.3(4) . . ?

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
C1 C2 C3 C4 0.8(8) . . . . ?
C1 C2 C3 C8 -178.7(5) . . . . ?
C1 C2 C5 C6 178.9(7) . . . . ?
C1 N1 S1 C16 72.7(6) . . . . ?
C1 N1 S1 O2 -42.0(6) . . . . ?
C1 N1 S1 O3 -171.1(5) . . . . ?
C2 C1 N1 C4 -20.8(6) . . . . ?
C2 C1 N1 S1 -168.1(4) . . . . ?
C2 C3 C4 N1 -13.0(7) . . . . ?
C2 C3 C8 C7 -1.0(9) . . . . ?
C2 C5 C6 C7 0.6(11) . . . . ?
C3 C2 C5 C6 -1.0(10) . . . . ?
C3 C4 N1 C1 21.1(6) . . . . ?
C3 C4 N1 S1 168.3(4) . . . . ?
C4 C3 C8 C7 179.6(6) . . . . ?
C4 N1 S1 C16 -71.6(6) . . . . ?
C4 N1 S1 O2 173.7(5) . . . . ?
C4 N1 S1 O3 44.5(6) . . . . ?
C5 C2 C3 C4 -179.2(6) . . . . ?
C5 C2 C3 C8 1.2(9) . . . . ?
C5 C6 C7 C8 -0.3(9) . . . . ?
C5 C6 C7 C9 -177.8(6) . . . . ?
C6 C7 C8 C3 0.5(8) . . . . ?
C6 C7 C9 C10 -3.4(8) . . . . ?
C6 C7 C9 C14 173.6(6) . . . . ?
C7 C9 C10 C11 174.1(6) . . . . ?
C7 C9 C14 C13 -175.5(6) . . . . ?
C8 C3 C4 N1 166.5(6) . . . . ?
C8 C7 C9 C10 179.2(6) . . . . ?
C8 C7 C9 C14 -3.8(8) . . . . ?
C9 C7 C8 C3 178.0(5) . . . . ?
C9 C10 C11 C12 2.6(11) . . . . ?
C10 C9 C14 C13 1.7(10) . . . . ?
C10 C11 C12 C13 -0.6(11) . . . . ?
C10 C11 C12 O1 -179.6(6) . . . . ?
C11 C12 C13 C14 -0.8(10) . . . . ?
C11 C12 O1 C15 169.9(7) . . . . ?
C12 C13 C14 C9 0.2(11) . . . . ?
C13 C12 O1 C15 -9.1(10) . . . . ?
C14 C9 C10 C11 -3.0(10) . . . . ?
C16 C17 C18 C19 -0.9(9) . . . . ?
C17 C16 C21 C20 1.1(10) . . . . ?
C17 C16 S1 N1 -91.6(5) . . . . ?
C17 C16 S1 O2 22.2(6) . . . . ?
C17 C16 S1 O3 153.6(5) . . . . ?
C17 C18 C19 C20 1.6(9) . . . . ?
C17 C18 C19 C22 -176.7(7) . . . . ?
C18 C19 C20 C21 -1.0(10) . . . . ?
C19 C20 C21 C16 -0.3(10) . . . . ?
C21 C16 C17 C18 -0.5(10) . . . . ?
C21 C16 S1 N1 86.4(6) . . . . ?
C21 C16 S1 O2 -159.7(5) . . . . ?
C21 C16 S1 O3 -28.3(6) . . . . ?
C22 C19 C20 C21 177.4(7) . . . . ?
N1 C1 C2 C3 12.0(7) . . . . ?
N1 C1 C2 C5 -167.9(6) . . . . ?
O1 C12 C13 C14 178.3(7) . . . . ?
S1 C16 C17 C18 177.5(5) . . . . ?
S1 C16 C21 C20 -177.0(5) . . . . ?

_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_3ea
_database_code_depnum_ccdc_archive 'CCDC 1491623'
_audit_update_record             
;
2017-12-29 deposited with the CCDC.
2018-01-23 downloaded from the CCDC.
;
_audit_creation_date             2017-12-27
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C21 H17 N O'
_chemical_formula_sum            'C21 H17 N O'
_chemical_formula_weight         299.36
_chemical_absolute_configuration unk
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H O N 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'
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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_H-M_alt        'P 1 c 1'
_space_group_name_Hall           'P -2yc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 'x, -y, z+1/2'

_cell_length_a                   15.5556(11)
_cell_length_b                   7.0185(5)
_cell_length_c                   7.3310(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.221(6)
_cell_angle_gamma                90.00
_cell_volume                     798.20(10)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1653
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      73.5210
_cell_measurement_theta_min      5.7310
_exptl_absorpt_coefficient_mu    0.595
_exptl_absorpt_correction_T_min  0.8702
_exptl_absorpt_correction_T_max  0.8901
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.246
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             316
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0400
_diffrn_reflns_av_unetI/netI     0.0375
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            2470
_diffrn_reflns_theta_full        67.03
_diffrn_reflns_theta_max         67.03
_diffrn_reflns_theta_min         5.70
_diffrn_ambient_temperature      294(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   16.00  115.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.5455   38.0000  120.0000 99

#__ type_ start__ end____ width___ exp.time_
  2 omega   87.00  163.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.1410   30.0000   60.0000 76

#__ type_ start__ end____ width___ exp.time_
  3 omega   71.00   97.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.5455 -125.0000   30.0000 26

#__ type_ start__ end____ width___ exp.time_
  4 omega   34.00   79.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.5455  -99.0000  120.0000 45

#__ type_ start__ end____ width___ exp.time_
  5 omega   41.00   87.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.1410  -30.0000  120.0000 46

#__ type_ start__ end____ width___ exp.time_
  6 omega   55.00   81.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.1410  -45.0000   90.0000 26

#__ type_ start__ end____ width___ exp.time_
  7 omega    5.00   32.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.5455  -99.0000  120.0000 27

#__ type_ start__ end____ width___ exp.time_
  8 omega   36.00   64.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.1410  -45.0000  -60.0000 28

#__ type_ start__ end____ width___ exp.time_
  9 omega   42.00   73.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.1410  -30.0000  -60.0000 31

#__ type_ start__ end____ width___ exp.time_
 10 omega   51.00   80.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.1410  -30.0000 -120.0000 29

#__ type_ start__ end____ width___ exp.time_
 11 omega   40.00   84.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.1410  -45.0000 -150.0000 44

#__ type_ start__ end____ width___ exp.time_
 12 omega   34.00  121.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.1410 -125.0000  -90.0000 87

#__ type_ start__ end____ width___ exp.time_
 13 omega  -60.00   -2.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.5455  125.0000  -60.0000 58
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0009711000
_diffrn_orient_matrix_UB_12      0.1444963000
_diffrn_orient_matrix_UB_13      0.1582833000
_diffrn_orient_matrix_UB_21      -0.0965038000
_diffrn_orient_matrix_UB_22      -0.0376555000
_diffrn_orient_matrix_UB_23      0.0193610000
_diffrn_orient_matrix_UB_31      0.0235086000
_diffrn_orient_matrix_UB_32      -0.1608611000
_diffrn_orient_matrix_UB_33      0.1376758000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                1508
_reflns_number_total             1658
_reflns_odcompleteness_completeness 99.68
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_refine_diff_density_max         0.235
_refine_diff_density_min         -0.392
_refine_diff_density_rms         0.067
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.3(8)
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.139
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         1658
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0737
_refine_ls_R_factor_gt           0.0712
_refine_ls_restrained_S_all      1.139
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1597P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2176
_refine_ls_wR_factor_ref         0.2227
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C4(H4A,H4B)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C7(H7), C8(H8), C10(H10), C11(H11), C12(H12), C13(H13), C14(H14),
 C16(H16), C17(H17), C18(H18), C19(H19), C20(H20)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
C1 C 0.4874(3) 0.2691(5) 0.3023(7) 0.0437(10) Uani 1 d . . .
H1A H 0.5004 0.3846 0.2370 0.052 Uiso 1 calc . . R
H1B H 0.4998 0.1596 0.2279 0.052 Uiso 1 calc . . R
C2 C 0.5368(4) 0.2608(4) 0.4846(6) 0.0431(10) Uani 1 d . . .
C3 C 0.4810(3) 0.2412(5) 0.6244(7) 0.0432(10) Uani 1 d . . .
C4 C 0.3890(4) 0.2443(6) 0.5482(7) 0.0526(13) Uani 1 d . . .
H4A H 0.3599 0.1261 0.5741 0.063 Uiso 1 calc . . R
H4B H 0.3578 0.3499 0.5976 0.063 Uiso 1 calc . . R
C5 C 0.6257(3) 0.2662(5) 0.5251(7) 0.0468(11) Uani 1 d . . .
H5 H 0.6628 0.2797 0.4320 0.056 Uiso 1 calc . . R
C6 C 0.6587(3) 0.2510(4) 0.7075(7) 0.0465(11) Uani 1 d . . .
C7 C 0.6014(4) 0.2319(5) 0.8438(7) 0.0500(11) Uani 1 d . . .
H7 H 0.6232 0.2212 0.9648 0.060 Uiso 1 calc . . R
C8 C 0.5131(4) 0.2282(6) 0.8050(7) 0.0519(12) Uani 1 d . . .
H8 H 0.4761 0.2173 0.8984 0.062 Uiso 1 calc . . R
C9 C 0.7540(3) 0.2524(5) 0.7557(7) 0.0481(11) Uani 1 d . . .
C10 C 0.8082(3) 0.3712(6) 0.6672(7) 0.0603(11) Uani 1 d . . .
H10 H 0.7855 0.4514 0.5749 0.072 Uiso 1 calc . . R
C11 C 0.8970(3) 0.3721(8) 0.7150(8) 0.0703(14) Uani 1 d . . .
H11 H 0.9333 0.4506 0.6534 0.084 Uiso 1 calc . . R
C12 C 0.9300(4) 0.2553(7) 0.8545(11) 0.0711(16) Uani 1 d . . .
H12 H 0.9887 0.2584 0.8899 0.085 Uiso 1 calc . . R
C13 C 0.8778(4) 0.1366(8) 0.9399(8) 0.0716(14) Uani 1 d . . .
H13 H 0.9011 0.0554 1.0309 0.086 Uiso 1 calc . . R
C14 C 0.7898(4) 0.1343(7) 0.8935(7) 0.0624(12) Uani 1 d . . .
H14 H 0.7545 0.0532 0.9548 0.075 Uiso 1 calc . . R
C15 C 0.2420(4) 0.2543(5) 0.2715(8) 0.0491(11) Uani 1 d . . .
C16 C 0.1866(3) 0.1132(6) 0.1973(7) 0.0588(11) Uani 1 d . . .
H16 H 0.2070 0.0211 0.1202 0.071 Uiso 1 calc . . R
C17 C 0.1008(3) 0.1112(7) 0.2391(7) 0.0671(13) Uani 1 d . . .
H17 H 0.0644 0.0152 0.1920 0.081 Uiso 1 calc . . R
C18 C 0.0692(4) 0.2494(8) 0.3494(9) 0.0740(19) Uani 1 d . . .
H18 H 0.0116 0.2478 0.3754 0.089 Uiso 1 calc . . R
C19 C 0.1235(3) 0.3899(8) 0.4207(7) 0.0673(14) Uani 1 d . . .
H19 H 0.1027 0.4834 0.4958 0.081 Uiso 1 calc . . R
C20 C 0.2098(3) 0.3920(6) 0.3804(7) 0.0581(11) Uani 1 d . . .
H20 H 0.2460 0.4881 0.4280 0.070 Uiso 1 calc . . R
C21 C 0.3336(3) 0.2554(5) 0.2165(7) 0.0472(11) Uani 1 d . . .
N1 N 0.3966(3) 0.2676(4) 0.3506(5) 0.0460(9) Uani 1 d . . .
O1 O 0.3474(3) 0.2481(4) 0.0561(6) 0.0650(11) Uani 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 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C1 C2 1.493(7) . ?
C1 N1 1.481(5) . ?
C2 C3 1.397(6) . ?
C2 C5 1.394(7) . ?
C3 C4 1.499(7) . ?
C3 C8 1.383(7) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 N1 1.471(7) . ?
C5 H5 0.9300 . ?
C5 C6 1.401(7) . ?
C6 C7 1.393(7) . ?
C6 C9 1.498(7) . ?
C7 H7 0.9300 . ?
C7 C8 1.381(8) . ?
C8 H8 0.9300 . ?
C9 C10 1.381(7) . ?
C9 C14 1.391(7) . ?
C10 H10 0.9300 . ?
C10 C11 1.399(7) . ?
C11 H11 0.9300 . ?
C11 C12 1.381(9) . ?
C12 H12 0.9300 . ?
C12 C13 1.349(9) . ?
C13 H13 0.9300 . ?
C13 C14 1.386(7) . ?
C14 H14 0.9300 . ?
C15 C16 1.396(7) . ?
C15 C20 1.371(7) . ?
C15 C21 1.510(7) . ?
C16 H16 0.9300 . ?
C16 C17 1.391(6) . ?
C17 H17 0.9300 . ?
C17 C18 1.376(8) . ?
C18 H18 0.9300 . ?
C18 C19 1.376(8) . ?
C19 H19 0.9300 . ?
C19 C20 1.397(6) . ?
C20 H20 0.9300 . ?
C21 N1 1.339(7) . ?
C21 O1 1.212(6) . ?

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
H1A C1 H1B 109.1 . . ?
C2 C1 H1A 111.2 . . ?
C2 C1 H1B 111.2 . . ?
N1 C1 H1A 111.2 . . ?
N1 C1 H1B 111.2 . . ?
N1 C1 C2 102.8(4) . . ?
C3 C2 C1 110.8(4) . . ?
C5 C2 C1 128.8(4) . . ?
C5 C2 C3 120.4(5) . . ?
C2 C3 C4 110.6(5) . . ?
C8 C3 C2 120.6(5) . . ?
C8 C3 C4 128.7(4) . . ?
C3 C4 H4A 111.2 . . ?
C3 C4 H4B 111.2 . . ?
H4A C4 H4B 109.1 . . ?
N1 C4 C3 103.0(4) . . ?
N1 C4 H4A 111.2 . . ?
N1 C4 H4B 111.2 . . ?
C2 C5 H5 120.4 . . ?
C2 C5 C6 119.3(4) . . ?
C6 C5 H5 120.4 . . ?
C5 C6 C9 120.7(5) . . ?
C7 C6 C5 118.9(5) . . ?
C7 C6 C9 120.4(5) . . ?
C6 C7 H7 118.9 . . ?
C8 C7 C6 122.2(5) . . ?
C8 C7 H7 118.9 . . ?
C3 C8 H8 120.7 . . ?
C7 C8 C3 118.6(4) . . ?
C7 C8 H8 120.7 . . ?
C10 C9 C6 121.4(4) . . ?
C10 C9 C14 118.3(5) . . ?
C14 C9 C6 120.3(4) . . ?
C9 C10 H10 119.6 . . ?
C9 C10 C11 120.7(5) . . ?
C11 C10 H10 119.6 . . ?
C10 C11 H11 120.3 . . ?
C12 C11 C10 119.3(5) . . ?
C12 C11 H11 120.3 . . ?
C11 C12 H12 119.8 . . ?
C13 C12 C11 120.4(6) . . ?
C13 C12 H12 119.8 . . ?
C12 C13 H13 119.7 . . ?
C12 C13 C14 120.7(5) . . ?
C14 C13 H13 119.7 . . ?
C9 C14 H14 119.7 . . ?
C13 C14 C9 120.5(5) . . ?
C13 C14 H14 119.7 . . ?
C16 C15 C21 117.9(4) . . ?
C20 C15 C16 119.1(5) . . ?
C20 C15 C21 122.9(4) . . ?
C15 C16 H16 120.1 . . ?
C17 C16 C15 119.7(4) . . ?
C17 C16 H16 120.1 . . ?
C16 C17 H17 119.6 . . ?
C18 C17 C16 120.8(5) . . ?
C18 C17 H17 119.6 . . ?
C17 C18 H18 120.2 . . ?
C17 C18 C19 119.5(5) . . ?
C19 C18 H18 120.2 . . ?
C18 C19 H19 120.0 . . ?
C18 C19 C20 120.0(4) . . ?
C20 C19 H19 120.0 . . ?
C15 C20 C19 120.9(5) . . ?
C15 C20 H20 119.6 . . ?
C19 C20 H20 119.6 . . ?
N1 C21 C15 117.3(4) . . ?
O1 C21 C15 119.8(5) . . ?
O1 C21 N1 122.9(5) . . ?
C4 N1 C1 112.6(4) . . ?
C21 N1 C1 118.9(4) . . ?
C21 N1 C4 127.5(4) . . ?

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
C1 C2 C3 C4 -2.8(4) . . . . ?
C1 C2 C3 C8 179.2(3) . . . . ?
C1 C2 C5 C6 -178.2(3) . . . . ?
C2 C1 N1 C4 -4.4(4) . . . . ?
C2 C1 N1 C21 -173.6(3) . . . . ?
C2 C3 C4 N1 0.0(4) . . . . ?
C2 C3 C8 C7 -1.1(6) . . . . ?
C2 C5 C6 C7 -0.3(5) . . . . ?
C2 C5 C6 C9 178.8(3) . . . . ?
C3 C2 C5 C6 0.2(5) . . . . ?
C3 C4 N1 C1 2.9(4) . . . . ?
C3 C4 N1 C21 171.0(3) . . . . ?
C4 C3 C8 C7 -178.7(3) . . . . ?
C5 C2 C3 C4 178.5(3) . . . . ?
C5 C2 C3 C8 0.5(5) . . . . ?
C5 C6 C7 C8 -0.3(5) . . . . ?
C5 C6 C9 C10 39.4(6) . . . . ?
C5 C6 C9 C14 -141.4(4) . . . . ?
C6 C7 C8 C3 1.0(6) . . . . ?
C6 C9 C10 C11 179.4(4) . . . . ?
C6 C9 C14 C13 -179.3(5) . . . . ?
C7 C6 C9 C10 -141.5(5) . . . . ?
C7 C6 C9 C14 37.7(6) . . . . ?
C8 C3 C4 N1 177.8(4) . . . . ?
C9 C6 C7 C8 -179.4(3) . . . . ?
C9 C10 C11 C12 -1.2(8) . . . . ?
C10 C9 C14 C13 0.0(7) . . . . ?
C10 C11 C12 C13 2.2(9) . . . . ?
C11 C12 C13 C14 -2.2(9) . . . . ?
C12 C13 C14 C9 1.1(8) . . . . ?
C14 C9 C10 C11 0.1(7) . . . . ?
C15 C16 C17 C18 1.6(8) . . . . ?
C15 C21 N1 C1 180.0(3) . . . . ?
C15 C21 N1 C4 12.5(6) . . . . ?
C16 C15 C20 C19 1.5(8) . . . . ?
C16 C15 C21 N1 -130.9(5) . . . . ?
C16 C15 C21 O1 50.1(6) . . . . ?
C16 C17 C18 C19 -0.8(8) . . . . ?
C17 C18 C19 C20 0.3(8) . . . . ?
C18 C19 C20 C15 -0.7(7) . . . . ?
C20 C15 C16 C17 -1.9(8) . . . . ?
C20 C15 C21 N1 53.5(6) . . . . ?
C20 C15 C21 O1 -125.5(5) . . . . ?
C21 C15 C16 C17 -177.7(4) . . . . ?
C21 C15 C20 C19 177.0(5) . . . . ?
N1 C1 C2 C3 4.3(4) . . . . ?
N1 C1 C2 C5 -177.1(3) . . . . ?
O1 C21 N1 C1 -1.1(6) . . . . ?
O1 C21 N1 C4 -168.6(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_3ah
_database_code_depnum_ccdc_archive 'CCDC 1491621'
_audit_update_record             
;
2017-12-29 deposited with the CCDC.
2018-01-23 downloaded from the CCDC.
;
_audit_creation_date             2017-12-27
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C21 H18 F N O2 S'
_chemical_formula_sum            'C21 H18 F N O2 S'
_chemical_formula_weight         367.42
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H O N 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'
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'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x, -y-1/2, z-1/2'

_cell_length_a                   19.4865(5)
_cell_length_b                   6.17720(10)
_cell_length_c                   15.7523(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 109.925(3)
_cell_angle_gamma                90.00
_cell_volume                     1782.63(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3672
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      73.5060
_cell_measurement_theta_min      4.3980
_exptl_absorpt_coefficient_mu    1.828
_exptl_absorpt_correction_T_max  0.7112
_exptl_absorpt_correction_T_min  0.6578
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.369
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0244
_diffrn_reflns_av_unetI/netI     0.0309
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            6380
_diffrn_reflns_theta_full        73.64
_diffrn_reflns_theta_max         73.64
_diffrn_reflns_theta_min         4.83
_diffrn_ambient_temperature      294(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.968
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -67.00   33.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.5455   57.0000  -60.0000 100

#__ type_ start__ end____ width___ exp.time_
  2 omega   -9.00   34.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.5455   38.0000 -150.0000 43

#__ type_ start__ end____ width___ exp.time_
  3 omega -103.00  -76.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.5455  -57.0000  150.0000 27

#__ type_ start__ end____ width___ exp.time_
  4 omega  -55.00  -12.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.5455  -57.0000  150.0000 43

#__ type_ start__ end____ width___ exp.time_
  5 omega  -83.00  -46.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.5455 -167.0000  -42.0000 37

#__ type_ start__ end____ width___ exp.time_
  6 omega   32.00   84.00   1.0000    1.2500
omega____ theta____ kappa____ phi______ frames
    -      107.1410  -30.0000    0.0000 52

#__ type_ start__ end____ width___ exp.time_
  7 omega   48.00   89.00   1.0000    1.2500
omega____ theta____ kappa____ phi______ frames
    -      107.1410  -45.0000   90.0000 41

#__ type_ start__ end____ width___ exp.time_
  8 omega   55.00   87.00   1.0000    1.2500
omega____ theta____ kappa____ phi______ frames
    -      107.1410  -95.0000   60.0000 32

#__ type_ start__ end____ width___ exp.time_
  9 omega   27.00  102.00   1.0000    1.2500
omega____ theta____ kappa____ phi______ frames
    -      107.1410  -95.0000 -150.0000 75

#__ type_ start__ end____ width___ exp.time_
 10 omega   37.00   88.00   1.0000    1.2500
omega____ theta____ kappa____ phi______ frames
    -      107.1410  -45.0000 -150.0000 51

#__ type_ start__ end____ width___ exp.time_
 11 omega   23.00  169.00   1.0000    1.2500
omega____ theta____ kappa____ phi______ frames
    -      107.1410    0.0000 -150.0000 146
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0697325000
_diffrn_orient_matrix_UB_12      0.0707715000
_diffrn_orient_matrix_UB_13      -0.0764655000
_diffrn_orient_matrix_UB_21      0.0450434000
_diffrn_orient_matrix_UB_22      0.0391385000
_diffrn_orient_matrix_UB_23      -0.0621796000
_diffrn_orient_matrix_UB_31      -0.0134232000
_diffrn_orient_matrix_UB_32      -0.2359368000
_diffrn_orient_matrix_UB_33      -0.0332125000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                3035
_reflns_number_total             3487
_reflns_odcompleteness_completeness 99.89
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_refine_diff_density_max         0.200
_refine_diff_density_min         -0.432
_refine_diff_density_rms         0.063
_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     236
_refine_ls_number_reflns         3487
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0542
_refine_ls_R_factor_gt           0.0492
_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     
'calc w=1/[σ²(Fo²)+(0.0841P)²+0.1884P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1395
_refine_ls_wR_factor_ref         0.1473
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_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:
 C1(H1A,H1B), C4(H4A,H4B)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C7(H7), C8(H8), C10(H10), C12(H12), C13(H13), C14(H14), C16(H16),
 C17(H17), C19(H19), C20(H20)
2.c Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
C1 C 0.69126(10) 0.2839(3) 0.73439(15) 0.0566(5) Uani 1 d . . .
H1A H 0.6817 0.1373 0.7494 0.068 Uiso 1 calc . . R
H1B H 0.7132 0.2796 0.6876 0.068 Uiso 1 calc . . R
C2 C 0.62325(10) 0.4181(3) 0.70627(12) 0.0482(4) Uani 1 d . . .
C3 C 0.63713(10) 0.6183(3) 0.74900(13) 0.0509(4) Uani 1 d . . .
C4 C 0.71514(11) 0.6319(3) 0.81023(15) 0.0603(5) Uani 1 d . . .
H4A H 0.7438 0.7222 0.7845 0.072 Uiso 1 calc . . R
H4B H 0.7189 0.6874 0.8693 0.072 Uiso 1 calc . . R
C5 C 0.55471(10) 0.3680(3) 0.64621(12) 0.0498(4) Uani 1 d . . .
H5 H 0.5463 0.2333 0.6182 0.060 Uiso 1 calc . . R
C6 C 0.49790(10) 0.5194(3) 0.62736(12) 0.0470(4) Uani 1 d . . .
C7 C 0.51356(11) 0.7203(3) 0.67072(14) 0.0563(5) Uani 1 d . . .
H7 H 0.4767 0.8236 0.6587 0.068 Uiso 1 calc . . R
C8 C 0.58187(11) 0.7700(3) 0.73073(15) 0.0588(5) Uani 1 d . . .
H8 H 0.5907 0.9047 0.7587 0.071 Uiso 1 calc . . R
C9 C 0.42279(10) 0.4670(3) 0.56583(11) 0.0488(4) Uani 1 d . . .
C10 C 0.40856(11) 0.2778(3) 0.51490(14) 0.0571(5) Uani 1 d . . .
H10 H 0.4463 0.1830 0.5175 0.069 Uiso 1 calc . . R
C11 C 0.33838(13) 0.2321(4) 0.46083(15) 0.0645(5) Uani 1 d . . .
C12 C 0.28007(13) 0.3612(4) 0.45363(15) 0.0711(6) Uani 1 d . . .
H12 H 0.2332 0.3245 0.4165 0.085 Uiso 1 calc . . R
C13 C 0.29372(13) 0.5486(5) 0.50384(17) 0.0800(7) Uani 1 d . . .
H13 H 0.2553 0.6413 0.5007 0.096 Uiso 1 calc . . R
C14 C 0.36344(12) 0.6007(4) 0.55866(15) 0.0684(6) Uani 1 d . . .
H14 H 0.3711 0.7285 0.5918 0.082 Uiso 1 calc . . R
C15 C 0.86483(9) 0.4209(3) 0.77824(13) 0.0521(4) Uani 1 d . . .
C16 C 0.86462(11) 0.2809(3) 0.70902(15) 0.0597(5) Uani 1 d . . .
H16 H 0.8449 0.1428 0.7059 0.072 Uiso 1 calc . . R
C17 C 0.89389(11) 0.3485(4) 0.64492(15) 0.0645(5) Uani 1 d . . .
H17 H 0.8939 0.2544 0.5988 0.077 Uiso 1 calc . . R
C18 C 0.92331(10) 0.5542(4) 0.64820(14) 0.0628(5) Uani 1 d . . .
C19 C 0.92314(10) 0.6911(3) 0.71831(15) 0.0608(5) Uani 1 d . . .
H19 H 0.9431 0.8290 0.7217 0.073 Uiso 1 calc . . R
C20 C 0.89409(10) 0.6271(3) 0.78288(14) 0.0567(5) Uani 1 d . . .
H20 H 0.8941 0.7211 0.8290 0.068 Uiso 1 calc . . R
C21 C 0.95537(14) 0.6268(6) 0.57821(18) 0.0931(9) Uani 1 d . . .
H21A H 1.0013 0.5555 0.5886 0.140 Uiso 1 calc . . GR
H21B H 0.9628 0.7806 0.5824 0.140 Uiso 1 calc . . GR
H21C H 0.9225 0.5905 0.5191 0.140 Uiso 1 calc . . GR
F1 F 0.32680(9) 0.0468(3) 0.41163(12) 0.1010(5) Uani 1 d . . .
N1 N 0.73798(9) 0.4024(3) 0.81507(11) 0.0559(4) Uani 1 d . . .
O1 O 0.82662(9) 0.1060(3) 0.86059(12) 0.0795(5) Uani 1 d . . .
O2 O 0.85438(9) 0.4623(3) 0.93748(10) 0.0793(5) Uani 1 d . . .
S1 S 0.82392(3) 0.33787(9) 0.85687(3) 0.06063(19) Uani 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 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C1 C2 1.496(3) . ?
C1 N1 1.480(2) . ?
C2 C3 1.390(2) . ?
C2 C5 1.383(2) . ?
C3 C4 1.500(3) . ?
C3 C8 1.382(3) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 N1 1.480(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.401(2) . ?
C6 C7 1.399(3) . ?
C6 C9 1.490(3) . ?
C7 H7 0.9300 . ?
C7 C8 1.379(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.391(3) . ?
C9 C14 1.394(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.372(3) . ?
C11 C12 1.361(3) . ?
C11 F1 1.357(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.376(4) . ?
C13 H13 0.9300 . ?
C13 C14 1.377(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.391(3) . ?
C15 C20 1.387(3) . ?
C15 S1 1.762(2) . ?
C16 H16 0.9300 . ?
C16 C17 1.383(3) . ?
C17 H17 0.9300 . ?
C17 C18 1.388(3) . ?
C18 C19 1.392(3) . ?
C18 C21 1.509(3) . ?
C19 H19 0.9300 . ?
C19 C20 1.380(3) . ?
C20 H20 0.9300 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
N1 S1 1.6264(17) . ?
O1 S1 1.4340(17) . ?
O2 S1 1.4291(16) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
H1A C1 H1B 109.3 . . ?
C2 C1 H1A 111.4 . . ?
C2 C1 H1B 111.4 . . ?
N1 C1 H1A 111.4 . . ?
N1 C1 H1B 111.4 . . ?
N1 C1 C2 101.77(15) . . ?
C3 C2 C1 110.06(16) . . ?
C5 C2 C1 129.03(16) . . ?
C5 C2 C3 120.90(17) . . ?
C2 C3 C4 110.41(16) . . ?
C8 C3 C2 119.56(18) . . ?
C8 C3 C4 130.03(17) . . ?
C3 C4 H4A 111.5 . . ?
C3 C4 H4B 111.5 . . ?
H4A C4 H4B 109.3 . . ?
N1 C4 C3 101.56(15) . . ?
N1 C4 H4A 111.5 . . ?
N1 C4 H4B 111.5 . . ?
C2 C5 H5 119.9 . . ?
C2 C5 C6 120.30(16) . . ?
C6 C5 H5 119.9 . . ?
C5 C6 C9 121.53(16) . . ?
C7 C6 C5 117.60(17) . . ?
C7 C6 C9 120.84(17) . . ?
C6 C7 H7 119.0 . . ?
C8 C7 C6 122.07(18) . . ?
C8 C7 H7 119.0 . . ?
C3 C8 H8 120.2 . . ?
C7 C8 C3 119.57(17) . . ?
C7 C8 H8 120.2 . . ?
C10 C9 C6 121.07(17) . . ?
C10 C9 C14 117.02(18) . . ?
C14 C9 C6 121.88(17) . . ?
C9 C10 H10 120.3 . . ?
C11 C10 C9 119.45(19) . . ?
C11 C10 H10 120.3 . . ?
C12 C11 C10 123.9(2) . . ?
F1 C11 C10 117.7(2) . . ?
F1 C11 C12 118.4(2) . . ?
C11 C12 H12 121.5 . . ?
C11 C12 C13 116.9(2) . . ?
C13 C12 H12 121.5 . . ?
C12 C13 H13 119.5 . . ?
C12 C13 C14 120.9(2) . . ?
C14 C13 H13 119.5 . . ?
C9 C14 H14 119.1 . . ?
C13 C14 C9 121.8(2) . . ?
C13 C14 H14 119.1 . . ?
C16 C15 S1 119.27(15) . . ?
C20 C15 C16 120.24(19) . . ?
C20 C15 S1 120.44(15) . . ?
C15 C16 H16 120.2 . . ?
C17 C16 C15 119.6(2) . . ?
C17 C16 H16 120.2 . . ?
C16 C17 H17 119.4 . . ?
C16 C17 C18 121.1(2) . . ?
C18 C17 H17 119.4 . . ?
C17 C18 C19 118.3(2) . . ?
C17 C18 C21 120.9(2) . . ?
C19 C18 C21 120.8(2) . . ?
C18 C19 H19 119.2 . . ?
C20 C19 C18 121.5(2) . . ?
C20 C19 H19 119.2 . . ?
C15 C20 H20 120.4 . . ?
C19 C20 C15 119.27(19) . . ?
C19 C20 H20 120.4 . . ?
C18 C21 H21A 109.5 . . ?
C18 C21 H21B 109.5 . . ?
C18 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C1 N1 C4 110.06(16) . . ?
C1 N1 S1 118.27(13) . . ?
C4 N1 S1 120.37(13) . . ?
N1 S1 C15 107.11(8) . . ?
O1 S1 C15 107.49(10) . . ?
O1 S1 N1 106.25(9) . . ?
O2 S1 C15 108.51(10) . . ?
O2 S1 N1 106.65(10) . . ?
O2 S1 O1 120.18(11) . . ?

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
C1 C2 C3 C4 -1.0(2) . . . . ?
C1 C2 C3 C8 178.41(18) . . . . ?
C1 C2 C5 C6 -178.62(18) . . . . ?
C1 N1 S1 C15 68.70(16) . . . . ?
C1 N1 S1 O1 -45.95(17) . . . . ?
C1 N1 S1 O2 -175.28(14) . . . . ?
C2 C1 N1 C4 -24.6(2) . . . . ?
C2 C1 N1 S1 -168.45(12) . . . . ?
C2 C3 C4 N1 -13.8(2) . . . . ?
C2 C3 C8 C7 0.4(3) . . . . ?
C2 C5 C6 C7 0.5(3) . . . . ?
C2 C5 C6 C9 -177.54(15) . . . . ?
C3 C2 C5 C6 0.1(3) . . . . ?
C3 C4 N1 C1 24.0(2) . . . . ?
C3 C4 N1 S1 166.96(13) . . . . ?
C4 C3 C8 C7 179.66(19) . . . . ?
C4 N1 S1 C15 -71.35(17) . . . . ?
C4 N1 S1 O1 174.00(16) . . . . ?
C4 N1 S1 O2 44.67(18) . . . . ?
C5 C2 C3 C4 -179.92(16) . . . . ?
C5 C2 C3 C8 -0.5(3) . . . . ?
C5 C6 C7 C8 -0.6(3) . . . . ?
C5 C6 C9 C10 -9.2(3) . . . . ?
C5 C6 C9 C14 168.76(18) . . . . ?
C6 C7 C8 C3 0.2(3) . . . . ?
C6 C9 C10 C11 178.23(18) . . . . ?
C6 C9 C14 C13 -178.0(2) . . . . ?
C7 C6 C9 C10 172.83(17) . . . . ?
C7 C6 C9 C14 -9.2(3) . . . . ?
C8 C3 C4 N1 166.90(19) . . . . ?
C9 C6 C7 C8 177.41(17) . . . . ?
C9 C10 C11 C12 -0.4(3) . . . . ?
C9 C10 C11 F1 179.47(19) . . . . ?
C10 C9 C14 C13 0.1(3) . . . . ?
C10 C11 C12 C13 0.4(4) . . . . ?
C11 C12 C13 C14 -0.1(4) . . . . ?
C12 C13 C14 C9 -0.1(4) . . . . ?
C14 C9 C10 C11 0.2(3) . . . . ?
C15 C16 C17 C18 -0.2(3) . . . . ?
C16 C15 C20 C19 -0.2(3) . . . . ?
C16 C15 S1 N1 -87.51(16) . . . . ?
C16 C15 S1 O1 26.31(18) . . . . ?
C16 C15 S1 O2 157.71(16) . . . . ?
C16 C17 C18 C19 0.5(3) . . . . ?
C16 C17 C18 C21 179.8(2) . . . . ?
C17 C18 C19 C20 -0.6(3) . . . . ?
C18 C19 C20 C15 0.5(3) . . . . ?
C20 C15 C16 C17 0.1(3) . . . . ?
C20 C15 S1 N1 89.68(16) . . . . ?
C20 C15 S1 O1 -156.50(16) . . . . ?
C20 C15 S1 O2 -25.10(19) . . . . ?
C21 C18 C19 C20 -180.0(2) . . . . ?
F1 C11 C12 C13 -179.5(2) . . . . ?
N1 C1 C2 C3 15.3(2) . . . . ?
N1 C1 C2 C5 -165.87(17) . . . . ?
S1 C15 C16 C17 177.31(15) . . . . ?
S1 C15 C20 C19 -177.39(14) . . . . ?

_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_3ad
_database_code_depnum_ccdc_archive 'CCDC 1491618'
_audit_update_record             
;
2017-12-29 deposited with the CCDC.
2018-01-23 downloaded from the CCDC.
;
_audit_creation_date             2017-12-27
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C22 H21 N O2 S'
_chemical_formula_sum            'C22 H21 N O2 S'
_chemical_formula_weight         363.46
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H O N 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'
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'

_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_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z'

_cell_length_a                   7.9693(2)
_cell_length_b                   6.1218(2)
_cell_length_c                   19.3280(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 101.204(2)
_cell_angle_gamma                90.00
_cell_volume                     924.97(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    7272
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      73.3580
_cell_measurement_theta_min      4.6670
_exptl_absorpt_coefficient_mu    1.674
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.54914
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.305
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             384
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.18
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0323
_diffrn_reflns_av_unetI/netI     0.0231
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            13752
_diffrn_reflns_theta_full        67.07
_diffrn_reflns_theta_max         67.07
_diffrn_reflns_theta_min         4.66
_diffrn_ambient_temperature      294(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3031
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -37.00   17.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      -40.5455   38.0000  -90.0000 54

#__ type_ start__ end____ width___ exp.time_
  2 omega  -50.00   34.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      -40.5455   38.0000   30.0000 84

#__ type_ start__ end____ width___ exp.time_
  3 omega  -95.00   -6.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      -40.5455  125.0000  120.0000 89

#__ type_ start__ end____ width___ exp.time_
  4 omega  -67.00   31.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      -40.5455   19.0000  150.0000 98

#__ type_ start__ end____ width___ exp.time_
  5 omega   23.00   49.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -       40.5455 -125.0000  -60.0000 26

#__ type_ start__ end____ width___ exp.time_
  6 omega   53.00   91.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -       40.5455 -125.0000   30.0000 38

#__ type_ start__ end____ width___ exp.time_
  7 omega   23.00   50.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -       40.5455 -125.0000  -30.0000 27

#__ type_ start__ end____ width___ exp.time_
  8 omega   42.00   91.00   1.0000   70.0000
omega____ theta____ kappa____ phi______ frames
    -      107.1410  -45.0000  -90.0000 49

#__ type_ start__ end____ width___ exp.time_
  9 omega   49.00  104.00   1.0000   70.0000
omega____ theta____ kappa____ phi______ frames
    -      107.1410  -95.0000  120.0000 55

#__ type_ start__ end____ width___ exp.time_
 10 omega   42.00   90.00   1.0000   70.0000
omega____ theta____ kappa____ phi______ frames
    -      107.1410  -30.0000   90.0000 48

#__ type_ start__ end____ width___ exp.time_
 11 omega   25.00  109.00   1.0000   70.0000
omega____ theta____ kappa____ phi______ frames
    -      107.1410  -95.0000   30.0000 84

#__ type_ start__ end____ width___ exp.time_
 12 omega   44.00   90.00   1.0000   70.0000
omega____ theta____ kappa____ phi______ frames
    -      107.1410  -30.0000   30.0000 46

#__ type_ start__ end____ width___ exp.time_
 13 omega   47.00  139.00   1.0000   70.0000
omega____ theta____ kappa____ phi______ frames
    -      107.1410  -77.0000 -180.0000 92

#__ type_ start__ end____ width___ exp.time_
 14 omega   54.00  160.00   1.0000   70.0000
omega____ theta____ kappa____ phi______ frames
    -      107.1410   15.0000    0.0000 106

#__ type_ start__ end____ width___ exp.time_
 15 omega   94.00  121.00   1.0000   70.0000
omega____ theta____ kappa____ phi______ frames
    -      107.1410 -125.0000  -60.0000 27

#__ type_ start__ end____ width___ exp.time_
 16 omega   84.00  171.00   1.0000   70.0000
omega____ theta____ kappa____ phi______ frames
    -      107.1410   30.0000   60.0000 87

#__ type_ start__ end____ width___ exp.time_
 17 omega   42.00   70.00   1.0000   70.0000
omega____ theta____ kappa____ phi______ frames
    -      107.1410 -125.0000  -60.0000 28

#__ type_ start__ end____ width___ exp.time_
 18 omega   39.00   81.00   1.0000   70.0000
omega____ theta____ kappa____ phi______ frames
    -      107.1410  -45.0000   90.0000 42

#__ type_ start__ end____ width___ exp.time_
 19 omega   31.00   85.00   1.0000   70.0000
omega____ theta____ kappa____ phi______ frames
    -      107.1410  -30.0000  150.0000 54

#__ type_ start__ end____ width___ exp.time_
 20 omega   45.00   88.00   1.0000   70.0000
omega____ theta____ kappa____ phi______ frames
    -      107.1410  -45.0000    0.0000 43

#__ type_ start__ end____ width___ exp.time_
 21 omega   71.00  109.00   1.0000   70.0000
omega____ theta____ kappa____ phi______ frames
    -      107.1410 -125.0000   30.0000 38

#__ type_ start__ end____ width___ exp.time_
 22 omega    8.00   48.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       40.7955   77.0000 -180.0000 40

#__ type_ start__ end____ width___ exp.time_
 23 omega    1.00   26.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       38.0000   90.0000    0.7496 25

#__ type_ start__ end____ width___ exp.time_
 24 omega   -1.00   25.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       38.0000   94.0000  129.9724 26

#__ type_ start__ end____ width___ exp.time_
 25 omega -100.00  -47.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      -40.7955  -57.0000  -30.0000 53

#__ type_ start__ end____ width___ exp.time_
 26 omega  -79.00  -53.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      -40.7955  -38.0000   90.0000 26

#__ type_ start__ end____ width___ exp.time_
 27 omega  -42.00  -16.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      -40.7955  -38.0000   90.0000 26

#__ type_ start__ end____ width___ exp.time_
 28 omega  -41.00  -13.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      -40.7955  -57.0000  -30.0000 28

#__ type_ start__ end____ width___ exp.time_
 29 omega  -40.00  -14.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      -40.7955  -57.0000  150.0000 26

#__ type_ start__ end____ width___ exp.time_
 30 omega -114.00  -88.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      -40.7955  -38.0000   90.0000 26

#__ type_ start__ end____ width___ exp.time_
 31 omega   18.00   45.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       50.0000   80.0000   38.7730 27

#__ type_ start__ end____ width___ exp.time_
 32 omega   19.00   44.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       50.0000   81.0000 -112.1148 25

#__ type_ start__ end____ width___ exp.time_
 33 omega   21.00   47.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   79.0000  164.2213 26

#__ type_ start__ end____ width___ exp.time_
 34 omega   21.00   46.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   79.0000  100.8808 25

#__ type_ start__ end____ width___ exp.time_
 35 omega   34.00   60.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       58.0000   76.0000 -125.8833 26

#__ type_ start__ end____ width___ exp.time_
 36 omega   34.00   68.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       62.0000   75.0000  -26.7581 34

#__ type_ start__ end____ width___ exp.time_
 37 omega   31.00   81.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       62.0000   77.0000 -167.1431 50

#__ type_ start__ end____ width___ exp.time_
 38 omega   33.00   64.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       66.0000   77.0000   25.4504 31

#__ type_ start__ end____ width___ exp.time_
 39 omega   33.00   72.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       66.0000   77.0000  -86.7803 39

#__ type_ start__ end____ width___ exp.time_
 40 omega   88.00  130.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       70.0000   77.0000   69.9721 42

#__ type_ start__ end____ width___ exp.time_
 41 omega   37.00   71.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       70.0000   77.0000   69.9721 34

#__ type_ start__ end____ width___ exp.time_
 42 omega   47.00   94.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       78.0000   72.0000  116.2167 47

#__ type_ start__ end____ width___ exp.time_
 43 omega   76.00  153.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      107.1410   77.0000 -150.0000 77

#__ type_ start__ end____ width___ exp.time_
 44 omega   75.00  100.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      107.1410   77.0000    0.0000 25

#__ type_ start__ end____ width___ exp.time_
 45 omega  125.00  151.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      107.1410   77.0000  120.0000 26

#__ type_ start__ end____ width___ exp.time_
 46 omega   75.00  114.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      107.1410   77.0000  120.0000 39

#__ type_ start__ end____ width___ exp.time_
 47 omega   80.00  163.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      107.1410   61.0000 -180.0000 83

#__ type_ start__ end____ width___ exp.time_
 48 omega   83.00  147.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      107.1410   61.0000  150.0000 64

#__ type_ start__ end____ width___ exp.time_
 49 omega   80.00  105.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      107.1410   61.0000  120.0000 25

#__ type_ start__ end____ width___ exp.time_
 50 omega   75.00  100.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      107.1410   77.0000  -90.0000 25

#__ type_ start__ end____ width___ exp.time_
 51 omega   76.00  101.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      107.1410   77.0000 -180.0000 25

#__ type_ start__ end____ width___ exp.time_
 52 omega   82.00  108.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      107.1410   61.0000  -60.0000 26

#__ type_ start__ end____ width___ exp.time_
 53 omega   75.00  100.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      107.1410   77.0000   30.0000 25

#__ type_ start__ end____ width___ exp.time_
 54 omega   75.00  101.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      107.1410   77.0000  150.0000 26

#__ type_ start__ end____ width___ exp.time_
 55 omega   75.00  101.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      107.1410   77.0000  -60.0000 26

#__ type_ start__ end____ width___ exp.time_
 56 omega  151.00  177.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      107.1410   61.0000   60.0000 26

#__ type_ start__ end____ width___ exp.time_
 57 omega   78.00  104.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      107.1410   61.0000   60.0000 26

#__ type_ start__ end____ width___ exp.time_
 58 omega   87.00  113.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      107.1410   61.0000  -30.0000 26

#__ type_ start__ end____ width___ exp.time_
 59 omega   80.00  111.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      107.1410   61.0000   90.0000 31

#__ type_ start__ end____ width___ exp.time_
 60 omega  117.00  173.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      107.1410   61.0000   90.0000 56

#__ type_ start__ end____ width___ exp.time_
 61 omega   75.00  128.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      107.1410   77.0000 -120.0000 53

#__ type_ start__ end____ width___ exp.time_
 62 omega   78.00  104.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      107.1410   77.0000  -30.0000 26
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.1632940000
_diffrn_orient_matrix_UB_12      -0.0187297000
_diffrn_orient_matrix_UB_13      -0.0311392000
_diffrn_orient_matrix_UB_21      0.1104180000
_diffrn_orient_matrix_UB_22      0.0245388000
_diffrn_orient_matrix_UB_23      0.0744462000
_diffrn_orient_matrix_UB_31      -0.0014526000
_diffrn_orient_matrix_UB_32      -0.2496345000
_diffrn_orient_matrix_UB_33      0.0096929000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2969
_reflns_number_total             3178
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'SIR2004 (Burla et al., 2007)'
_refine_diff_density_max         0.086
_refine_diff_density_min         -0.169
_refine_diff_density_rms         0.027
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.002(15)
_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     237
_refine_ls_number_reflns         3178
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0345
_refine_ls_R_factor_gt           0.0307
_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     
'calc w=1/[σ²(Fo²)+(0.0514P)²+0.0493P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0818
_refine_ls_wR_factor_ref         0.0845
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_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:
 C1(H1A,H1B), C4(H4A,H4B)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C7(H7), C8(H8), C10(H10), C11(H11), C13(H13), C14(H14), C17(H17),
 C18(H18), C20(H20), C21(H21)
2.c Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C22(H22A,H22B,H22C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
C1 C 0.0737(3) 0.5101(4) 0.30138(10) 0.0683(5) Uani 1 d . . .
H1A H 0.1679 0.5178 0.2764 0.082 Uiso 1 calc . . R
H1B H 0.0538 0.3589 0.3124 0.082 Uiso 1 calc . . R
C2 C 0.1065(2) 0.6502(3) 0.36694(9) 0.0550(4) Uani 1 d . . .
C3 C 0.0124(2) 0.8405(3) 0.35514(9) 0.0569(4) Uani 1 d . . .
C4 C -0.0972(3) 0.8409(4) 0.28272(10) 0.0663(5) Uani 1 d . . .
H4A H -0.2148 0.8783 0.2841 0.080 Uiso 1 calc . . R
H4B H -0.0537 0.9416 0.2517 0.080 Uiso 1 calc . . R
C5 C 0.2152(2) 0.6113(3) 0.43083(9) 0.0565(4) Uani 1 d . . .
H5 H 0.2780 0.4824 0.4377 0.068 Uiso 1 calc . . R
C6 C 0.2309(2) 0.7662(3) 0.48533(9) 0.0519(4) Uani 1 d . . .
C7 C 0.1351(3) 0.9568(4) 0.47160(10) 0.0630(5) Uani 1 d . . .
H7 H 0.1439 1.0620 0.5069 0.076 Uiso 1 calc . . R
C8 C 0.0276(3) 0.9961(4) 0.40782(10) 0.0665(5) Uani 1 d . . .
H8 H -0.0340 1.1259 0.4003 0.080 Uiso 1 calc . . R
C9 C 0.3385(2) 0.7239(3) 0.55600(10) 0.0519(4) Uani 1 d . . .
C10 C 0.4227(3) 0.5273(5) 0.57240(10) 0.0755(6) Uani 1 d . . .
H10 H 0.4204 0.4236 0.5371 0.091 Uiso 1 calc . . R
C11 C 0.5101(3) 0.4807(4) 0.63991(12) 0.0796(7) Uani 1 d . . .
H11 H 0.5646 0.3464 0.6487 0.096 Uiso 1 calc . . R
C12 C 0.5186(2) 0.6274(4) 0.69437(10) 0.0628(5) Uani 1 d . . .
C13 C 0.4380(3) 0.8244(4) 0.67838(12) 0.0770(6) Uani 1 d . . .
H13 H 0.4424 0.9283 0.7138 0.092 Uiso 1 calc . . R
C14 C 0.3508(3) 0.8727(4) 0.61130(12) 0.0747(6) Uani 1 d . . .
H14 H 0.2987 1.0086 0.6027 0.090 Uiso 1 calc . . R
C15 C 0.6055(3) 0.5686(5) 0.76834(12) 0.0867(7) Uani 1 d . . .
H15A H 0.7272 0.5793 0.7725 0.130 Uiso 1 calc . . GR
H15B H 0.5757 0.4217 0.7786 0.130 Uiso 1 calc . . GR
H15C H 0.5690 0.6671 0.8011 0.130 Uiso 1 calc . . GR
C16 C -0.0098(2) 0.6568(3) 0.12930(9) 0.0557(4) Uani 1 d . . .
C17 C 0.1378(2) 0.5432(4) 0.12374(9) 0.0624(4) Uani 1 d . . .
H17 H 0.1565 0.4039 0.1429 0.075 Uiso 1 calc . . R
C18 C 0.2563(3) 0.6372(4) 0.08982(10) 0.0664(5) Uani 1 d . . .
H18 H 0.3553 0.5608 0.0865 0.080 Uiso 1 calc . . R
C19 C 0.2303(3) 0.8439(4) 0.06058(10) 0.0629(5) Uani 1 d . . .
C20 C 0.0800(3) 0.9526(4) 0.06521(10) 0.0618(4) Uani 1 d . . .
H20 H 0.0591 1.0893 0.0443 0.074 Uiso 1 calc . . R
C21 C -0.0392(2) 0.8630(3) 0.10005(9) 0.0576(4) Uani 1 d . . .
H21 H -0.1377 0.9398 0.1038 0.069 Uiso 1 calc . . R
C22 C 0.3624(3) 0.9465(6) 0.02515(14) 0.0955(8) Uani 1 d . . .
H22A H 0.4746 0.9108 0.0509 0.143 Uiso 1 calc . . GR
H22B H 0.3479 1.1022 0.0241 0.143 Uiso 1 calc . . GR
H22C H 0.3492 0.8922 -0.0222 0.143 Uiso 1 calc . . GR
N1 N -0.0822(2) 0.6127(3) 0.26069(8) 0.0629(4) Uani 1 d . . .
O1 O -0.1380(3) 0.3111(3) 0.17618(9) 0.0877(5) Uani 1 d . . .
O2 O -0.31447(18) 0.6476(3) 0.15774(8) 0.0838(5) Uani 1 d . . .
S1 S -0.15209(6) 0.54349(9) 0.17887(2) 0.06553(15) Uani 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 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C1 C2 1.510(3) . ?
C1 N1 1.475(3) . ?
C2 C3 1.380(3) . ?
C2 C5 1.385(3) . ?
C3 C4 1.499(3) . ?
C3 C8 1.382(3) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 N1 1.472(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.404(3) . ?
C6 C7 1.392(3) . ?
C6 C9 1.488(3) . ?
C7 H7 0.9300 . ?
C7 C8 1.379(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.385(3) . ?
C9 C14 1.393(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.384(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.375(3) . ?
C12 C13 1.373(3) . ?
C12 C15 1.506(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.379(3) . ?
C14 H14 0.9300 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 C17 1.388(3) . ?
C16 C21 1.384(3) . ?
C16 S1 1.7628(19) . ?
C17 H17 0.9300 . ?
C17 C18 1.376(3) . ?
C18 H18 0.9300 . ?
C18 C19 1.385(3) . ?
C19 C20 1.388(3) . ?
C19 C22 1.500(3) . ?
C20 H20 0.9300 . ?
C20 C21 1.381(3) . ?
C21 H21 0.9300 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
N1 S1 1.6273(16) . ?
O1 S1 1.429(2) . ?
O2 S1 1.4290(17) . ?

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
H1A C1 H1B 109.3 . . ?
C2 C1 H1A 111.5 . . ?
C2 C1 H1B 111.5 . . ?
N1 C1 H1A 111.5 . . ?
N1 C1 H1B 111.5 . . ?
N1 C1 C2 101.30(17) . . ?
C3 C2 C1 109.94(17) . . ?
C3 C2 C5 121.20(18) . . ?
C5 C2 C1 128.84(17) . . ?
C2 C3 C4 110.79(18) . . ?
C2 C3 C8 119.54(18) . . ?
C8 C3 C4 129.67(18) . . ?
C3 C4 H4A 111.4 . . ?
C3 C4 H4B 111.4 . . ?
H4A C4 H4B 109.3 . . ?
N1 C4 C3 101.72(16) . . ?
N1 C4 H4A 111.4 . . ?
N1 C4 H4B 111.4 . . ?
C2 C5 H5 119.9 . . ?
C2 C5 C6 120.13(17) . . ?
C6 C5 H5 119.9 . . ?
C5 C6 C9 121.51(16) . . ?
C7 C6 C5 117.24(17) . . ?
C7 C6 C9 121.18(17) . . ?
C6 C7 H7 118.7 . . ?
C8 C7 C6 122.63(18) . . ?
C8 C7 H7 118.7 . . ?
C3 C8 H8 120.4 . . ?
C7 C8 C3 119.25(18) . . ?
C7 C8 H8 120.4 . . ?
C10 C9 C6 121.91(16) . . ?
C10 C9 C14 115.70(19) . . ?
C14 C9 C6 122.23(18) . . ?
C9 C10 H10 119.1 . . ?
C11 C10 C9 121.8(2) . . ?
C11 C10 H10 119.1 . . ?
C10 C11 H11 119.1 . . ?
C12 C11 C10 121.9(2) . . ?
C12 C11 H11 119.1 . . ?
C11 C12 C15 121.0(2) . . ?
C13 C12 C11 116.7(2) . . ?
C13 C12 C15 122.2(2) . . ?
C12 C13 H13 119.1 . . ?
C12 C13 C14 121.9(2) . . ?
C14 C13 H13 119.1 . . ?
C9 C14 H14 119.0 . . ?
C13 C14 C9 121.9(2) . . ?
C13 C14 H14 119.0 . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C17 C16 S1 119.28(15) . . ?
C21 C16 C17 120.27(18) . . ?
C21 C16 S1 120.32(14) . . ?
C16 C17 H17 120.1 . . ?
C18 C17 C16 119.8(2) . . ?
C18 C17 H17 120.1 . . ?
C17 C18 H18 119.5 . . ?
C17 C18 C19 120.95(19) . . ?
C19 C18 H18 119.5 . . ?
C18 C19 C20 118.32(19) . . ?
C18 C19 C22 120.4(2) . . ?
C20 C19 C22 121.3(2) . . ?
C19 C20 H20 119.2 . . ?
C21 C20 C19 121.66(19) . . ?
C21 C20 H20 119.2 . . ?
C16 C21 H21 120.5 . . ?
C20 C21 C16 118.92(18) . . ?
C20 C21 H21 120.5 . . ?
C19 C22 H22A 109.5 . . ?
C19 C22 H22B 109.5 . . ?
C19 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C1 N1 S1 120.07(14) . . ?
C4 N1 C1 110.92(16) . . ?
C4 N1 S1 119.76(13) . . ?
N1 S1 C16 106.91(8) . . ?
O1 S1 C16 107.98(11) . . ?
O1 S1 N1 106.27(10) . . ?
O1 S1 O2 120.44(12) . . ?
O2 S1 C16 108.16(9) . . ?
O2 S1 N1 106.36(10) . . ?

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
C1 C2 C3 C4 2.7(2) . . . . ?
C1 C2 C3 C8 -177.93(18) . . . . ?
C1 C2 C5 C6 178.38(19) . . . . ?
C1 N1 S1 C16 -72.23(18) . . . . ?
C1 N1 S1 O1 42.90(19) . . . . ?
C1 N1 S1 O2 172.37(16) . . . . ?
C2 C1 N1 C4 23.3(2) . . . . ?
C2 C1 N1 S1 169.99(13) . . . . ?
C2 C3 C4 N1 11.4(2) . . . . ?
C2 C3 C8 C7 -0.8(3) . . . . ?
C2 C5 C6 C7 -0.7(3) . . . . ?
C2 C5 C6 C9 176.31(16) . . . . ?
C3 C2 C5 C6 0.4(3) . . . . ?
C3 C4 N1 C1 -21.9(2) . . . . ?
C3 C4 N1 S1 -168.68(12) . . . . ?
C4 C3 C8 C7 178.4(2) . . . . ?
C4 N1 S1 C16 71.50(17) . . . . ?
C4 N1 S1 O1 -173.36(16) . . . . ?
C4 N1 S1 O2 -43.89(18) . . . . ?
C5 C2 C3 C4 -178.92(17) . . . . ?
C5 C2 C3 C8 0.4(3) . . . . ?
C5 C6 C7 C8 0.3(3) . . . . ?
C5 C6 C9 C10 -2.7(3) . . . . ?
C5 C6 C9 C14 -177.82(19) . . . . ?
C6 C7 C8 C3 0.5(3) . . . . ?
C6 C9 C10 C11 -174.1(2) . . . . ?
C6 C9 C14 C13 174.0(2) . . . . ?
C7 C6 C9 C10 174.26(19) . . . . ?
C7 C6 C9 C14 -0.9(3) . . . . ?
C8 C3 C4 N1 -167.91(19) . . . . ?
C9 C6 C7 C8 -176.72(18) . . . . ?
C9 C10 C11 C12 -0.2(4) . . . . ?
C10 C9 C14 C13 -1.5(3) . . . . ?
C10 C11 C12 C13 -0.9(4) . . . . ?
C10 C11 C12 C15 176.4(2) . . . . ?
C11 C12 C13 C14 0.8(4) . . . . ?
C12 C13 C14 C9 0.4(4) . . . . ?
C14 C9 C10 C11 1.4(3) . . . . ?
C15 C12 C13 C14 -176.4(2) . . . . ?
C16 C17 C18 C19 -0.4(3) . . . . ?
C17 C16 C21 C20 0.2(3) . . . . ?
C17 C16 S1 N1 85.07(16) . . . . ?
C17 C16 S1 O1 -28.91(18) . . . . ?
C17 C16 S1 O2 -160.75(15) . . . . ?
C17 C18 C19 C20 -1.1(3) . . . . ?
C17 C18 C19 C22 178.6(2) . . . . ?
C18 C19 C20 C21 2.3(3) . . . . ?
C19 C20 C21 C16 -1.8(3) . . . . ?
C21 C16 C17 C18 0.9(3) . . . . ?
C21 C16 S1 N1 -90.81(16) . . . . ?
C21 C16 S1 O1 155.21(15) . . . . ?
C21 C16 S1 O2 23.37(18) . . . . ?
C22 C19 C20 C21 -177.5(2) . . . . ?
N1 C1 C2 C3 -15.5(2) . . . . ?
N1 C1 C2 C5 166.28(19) . . . . ?
S1 C16 C17 C18 -175.00(15) . . . . ?
S1 C16 C21 C20 176.06(14) . . . . ?

_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_3ac
_database_code_depnum_ccdc_archive 'CCDC 1491617'
_audit_update_record             
;
2017-12-29 deposited with the CCDC.
2018-01-23 downloaded from the CCDC.
;
_audit_creation_date             2017-12-27
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C23 H23 N O3 S'
_chemical_formula_sum            'C23 H23 N O3 S'
_chemical_formula_weight         393.48
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H O N S'
_chemical_oxdiff_usercomment     ZYY-2
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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, -y, z+1/2'
3 '-x, y+1/2, -z+1/2'
4 'x+1/2, -y+1/2, -z'

_cell_length_a                   8.4634(2)
_cell_length_b                   9.3587(2)
_cell_length_c                   25.6617(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2032.57(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3141
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      73.4470
_cell_measurement_theta_min      5.0360
_exptl_absorpt_coefficient_mu    1.601
_exptl_absorpt_correction_T_min  0.87136
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.286
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             832
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.23
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0134
_diffrn_reflns_av_unetI/netI     0.0216
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            5167
_diffrn_reflns_theta_full        73.57
_diffrn_reflns_theta_max         73.57
_diffrn_reflns_theta_min         3.44
_diffrn_ambient_temperature      294(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega -114.00  -12.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.5455  -57.0000   60.0000 102

#__ type_ start__ end____ width___ exp.time_
  2 omega  -48.00  -12.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.5455   38.0000 -150.0000 36

#__ type_ start__ end____ width___ exp.time_
  3 omega   65.00   91.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       40.5455 -125.0000  -30.0000 26

#__ type_ start__ end____ width___ exp.time_
  4 omega   70.00   96.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      107.1410  -45.0000  -60.0000 26

#__ type_ start__ end____ width___ exp.time_
  5 omega   26.00   95.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      107.1410  -95.0000  -30.0000 69

#__ type_ start__ end____ width___ exp.time_
  6 omega   51.00   78.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      107.1410  -30.0000  150.0000 27

#__ type_ start__ end____ width___ exp.time_
  7 omega   56.00  175.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      107.1410   15.0000  120.0000 119

#__ type_ start__ end____ width___ exp.time_
  8 omega   51.00   76.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      107.1410  -30.0000 -150.0000 25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0629723000
_diffrn_orient_matrix_UB_12      0.1043621000
_diffrn_orient_matrix_UB_13      0.0415084000
_diffrn_orient_matrix_UB_21      -0.0034959000
_diffrn_orient_matrix_UB_22      0.1206450000
_diffrn_orient_matrix_UB_23      -0.0408545000
_diffrn_orient_matrix_UB_31      -0.1707756000
_diffrn_orient_matrix_UB_32      -0.0407837000
_diffrn_orient_matrix_UB_33      -0.0144732000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                3184
_reflns_number_total             3393
_reflns_odcompleteness_completeness 99.81
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.098
_refine_diff_density_min         -0.318
_refine_diff_density_rms         0.030
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.004(18)
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         3393
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0349
_refine_ls_R_factor_gt           0.0325
_refine_ls_restrained_S_all      1.028
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0493P)²+0.1851P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0859
_refine_ls_wR_factor_ref         0.0885
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_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:
 C1(H1A,H1B), C4(H4A,H4B), C15(H15A,H15B)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C7(H7), C8(H8), C10(H10), C11(H11), C13(H13), C14(H14), C18(H18),
 C19(H19), C21(H21), C22(H22)
2.c 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   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
C1 C -0.0432(2) 0.9084(3) 0.63083(8) 0.0566(5) Uani 1 d . . .
H1A H -0.0142 1.0070 0.6241 0.068 Uiso 1 calc . . R
H1B H -0.0058 0.8487 0.6025 0.068 Uiso 1 calc . . R
C2 C 0.0194(2) 0.85796(19) 0.68279(7) 0.0477(4) Uani 1 d . . .
C3 C -0.0996(2) 0.7899(2) 0.71041(8) 0.0489(4) Uani 1 d . . .
C4 C -0.2526(2) 0.7912(2) 0.68087(8) 0.0572(5) Uani 1 d . . .
H4A H -0.2781 0.6973 0.6673 0.069 Uiso 1 calc . . R
H4B H -0.3391 0.8249 0.7024 0.069 Uiso 1 calc . . R
C5 C 0.1699(2) 0.87195(19) 0.70324(7) 0.0485(4) Uani 1 d . . .
H5 H 0.2491 0.9165 0.6841 0.058 Uiso 1 calc . . R
C6 C 0.2016(2) 0.81805(19) 0.75322(7) 0.0460(4) Uani 1 d . . .
C7 C 0.0808(2) 0.7480(2) 0.77988(8) 0.0546(4) Uani 1 d . . .
H7 H 0.1016 0.7103 0.8127 0.065 Uiso 1 calc . . R
C8 C -0.0697(2) 0.7328(2) 0.75893(8) 0.0556(5) Uani 1 d . . .
H8 H -0.1486 0.6851 0.7772 0.067 Uiso 1 calc . . R
C9 C 0.3571(2) 0.83748(19) 0.77934(7) 0.0457(4) Uani 1 d . . .
C10 C 0.4486(2) 0.9591(2) 0.77213(7) 0.0500(4) Uani 1 d . . .
H10 H 0.4149 1.0281 0.7486 0.060 Uiso 1 calc . . R
C11 C 0.5890(2) 0.9808(2) 0.79909(7) 0.0528(4) Uani 1 d . . .
H11 H 0.6483 1.0630 0.7934 0.063 Uiso 1 calc . . R
C12 C 0.6401(2) 0.8790(2) 0.83456(7) 0.0491(4) Uani 1 d . . .
C13 C 0.5521(2) 0.7550(2) 0.84159(8) 0.0515(4) Uani 1 d . . .
H13 H 0.5871 0.6852 0.8646 0.062 Uiso 1 calc . . R
C14 C 0.4135(2) 0.7354(2) 0.81459(7) 0.0496(4) Uani 1 d . . .
H14 H 0.3557 0.6522 0.8199 0.060 Uiso 1 calc . . R
C15 C 0.8695(3) 1.0131(3) 0.86019(10) 0.0711(6) Uani 1 d . . .
H15A H 0.8089 1.0985 0.8680 0.085 Uiso 1 calc . . R
H15B H 0.9117 1.0213 0.8252 0.085 Uiso 1 calc . . R
C16 C 1.0008(4) 0.9940(3) 0.89905(13) 0.0984(10) Uani 1 d . . .
H16A H 0.9576 0.9922 0.9336 0.148 Uiso 1 calc . . GR
H16B H 1.0740 1.0719 0.8961 0.148 Uiso 1 calc . . GR
H16C H 1.0547 0.9057 0.8923 0.148 Uiso 1 calc . . GR
C17 C -0.3453(2) 0.7471(2) 0.55649(7) 0.0515(4) Uani 1 d . . .
C18 C -0.2521(3) 0.7286(3) 0.51256(8) 0.0650(5) Uani 1 d . . .
H18 H -0.1887 0.8024 0.5003 0.078 Uiso 1 calc . . R
C19 C -0.2554(3) 0.5974(3) 0.48731(8) 0.0731(6) Uani 1 d . . .
H19 H -0.1945 0.5847 0.4575 0.088 Uiso 1 calc . . R
C20 C -0.3458(3) 0.4863(3) 0.50501(8) 0.0682(6) Uani 1 d . . .
C21 C -0.4393(3) 0.5087(2) 0.54902(8) 0.0666(6) Uani 1 d . . .
H21 H -0.5026 0.4349 0.5614 0.080 Uiso 1 calc . . R
C22 C -0.4393(3) 0.6377(2) 0.57423(8) 0.0582(5) Uani 1 d . . .
H22 H -0.5029 0.6512 0.6034 0.070 Uiso 1 calc . . R
C23 C -0.3474(5) 0.3428(3) 0.47779(12) 0.1104(12) Uani 1 d . . .
H23A H -0.4541 0.3177 0.4690 0.166 Uiso 1 calc . . GR
H23B H -0.3039 0.2715 0.5005 0.166 Uiso 1 calc . . GR
H23C H -0.2852 0.3482 0.4466 0.166 Uiso 1 calc . . GR
N1 N -0.2162(2) 0.8930(2) 0.63857(7) 0.0576(4) Uani 1 d . . .
O1 O 0.77253(18) 0.88844(16) 0.86477(6) 0.0632(4) Uani 1 d . . .
O2 O -0.2781(3) 1.01862(18) 0.55750(8) 0.0867(6) Uani 1 d . . .
O3 O -0.49235(19) 0.9277(2) 0.61504(7) 0.0799(5) Uani 1 d . . .
S1 S -0.34033(7) 0.91053(6) 0.59094(2) 0.06198(15) Uani 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 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C1 C2 1.511(3) . ?
C1 N1 1.484(3) . ?
C2 C3 1.386(3) . ?
C2 C5 1.384(3) . ?
C3 C4 1.501(3) . ?
C3 C8 1.378(3) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 N1 1.477(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.404(3) . ?
C6 C7 1.393(3) . ?
C6 C9 1.488(3) . ?
C7 H7 0.9300 . ?
C7 C8 1.390(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.389(3) . ?
C9 C14 1.399(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.390(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.387(3) . ?
C12 C13 1.391(3) . ?
C12 O1 1.366(2) . ?
C13 H13 0.9300 . ?
C13 C14 1.374(3) . ?
C14 H14 0.9300 . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 C16 1.504(3) . ?
C15 O1 1.431(3) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 C18 1.387(3) . ?
C17 C22 1.374(3) . ?
C17 S1 1.767(2) . ?
C18 H18 0.9300 . ?
C18 C19 1.388(4) . ?
C19 H19 0.9300 . ?
C19 C20 1.368(4) . ?
C20 C21 1.395(3) . ?
C20 C23 1.514(3) . ?
C21 H21 0.9300 . ?
C21 C22 1.370(3) . ?
C22 H22 0.9300 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
N1 S1 1.6201(17) . ?
O2 S1 1.4273(19) . ?
O3 S1 1.4366(18) . ?

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
H1A C1 H1B 109.3 . . ?
C2 C1 H1A 111.5 . . ?
C2 C1 H1B 111.5 . . ?
N1 C1 H1A 111.5 . . ?
N1 C1 H1B 111.5 . . ?
N1 C1 C2 101.38(16) . . ?
C3 C2 C1 109.90(17) . . ?
C5 C2 C1 128.91(18) . . ?
C5 C2 C3 121.19(17) . . ?
C2 C3 C4 111.40(16) . . ?
C8 C3 C2 120.48(18) . . ?
C8 C3 C4 128.12(18) . . ?
C3 C4 H4A 111.5 . . ?
C3 C4 H4B 111.5 . . ?
H4A C4 H4B 109.3 . . ?
N1 C4 C3 101.33(16) . . ?
N1 C4 H4A 111.5 . . ?
N1 C4 H4B 111.5 . . ?
C2 C5 H5 120.4 . . ?
C2 C5 C6 119.22(17) . . ?
C6 C5 H5 120.4 . . ?
C5 C6 C9 122.43(17) . . ?
C7 C6 C5 118.52(17) . . ?
C7 C6 C9 119.01(16) . . ?
C6 C7 H7 119.0 . . ?
C8 C7 C6 122.04(18) . . ?
C8 C7 H7 119.0 . . ?
C3 C8 C7 118.50(19) . . ?
C3 C8 H8 120.7 . . ?
C7 C8 H8 120.7 . . ?
C10 C9 C6 122.22(17) . . ?
C10 C9 C14 117.07(17) . . ?
C14 C9 C6 120.63(17) . . ?
C9 C10 H10 119.0 . . ?
C9 C10 C11 122.00(18) . . ?
C11 C10 H10 119.0 . . ?
C10 C11 H11 120.2 . . ?
C12 C11 C10 119.53(17) . . ?
C12 C11 H11 120.2 . . ?
C11 C12 C13 119.43(18) . . ?
O1 C12 C11 125.72(17) . . ?
O1 C12 C13 114.84(17) . . ?
C12 C13 H13 119.9 . . ?
C14 C13 C12 120.21(18) . . ?
C14 C13 H13 119.9 . . ?
C9 C14 H14 119.1 . . ?
C13 C14 C9 121.73(17) . . ?
C13 C14 H14 119.1 . . ?
H15A C15 H15B 108.7 . . ?
C16 C15 H15A 110.6 . . ?
C16 C15 H15B 110.6 . . ?
O1 C15 H15A 110.6 . . ?
O1 C15 H15B 110.6 . . ?
O1 C15 C16 105.8(2) . . ?
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 S1 120.08(17) . . ?
C22 C17 C18 120.4(2) . . ?
C22 C17 S1 119.53(15) . . ?
C17 C18 H18 120.7 . . ?
C17 C18 C19 118.6(2) . . ?
C19 C18 H18 120.7 . . ?
C18 C19 H19 119.1 . . ?
C20 C19 C18 121.9(2) . . ?
C20 C19 H19 119.1 . . ?
C19 C20 C21 118.2(2) . . ?
C19 C20 C23 121.7(3) . . ?
C21 C20 C23 120.1(3) . . ?
C20 C21 H21 119.5 . . ?
C22 C21 C20 121.0(2) . . ?
C22 C21 H21 119.5 . . ?
C17 C22 H22 120.0 . . ?
C21 C22 C17 120.00(19) . . ?
C21 C22 H22 120.0 . . ?
C20 C23 H23A 109.5 . . ?
C20 C23 H23B 109.5 . . ?
C20 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C1 N1 S1 121.92(15) . . ?
C4 N1 C1 111.54(16) . . ?
C4 N1 S1 119.00(14) . . ?
C12 O1 C15 118.47(16) . . ?
N1 S1 C17 107.75(9) . . ?
O2 S1 C17 108.75(10) . . ?
O2 S1 N1 106.62(11) . . ?
O2 S1 O3 120.67(13) . . ?
O3 S1 C17 106.92(11) . . ?
O3 S1 N1 105.51(10) . . ?

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
C1 C2 C3 C4 -1.5(2) . . . . ?
C1 C2 C3 C8 179.11(18) . . . . ?
C1 C2 C5 C6 179.11(19) . . . . ?
C1 N1 S1 C17 81.5(2) . . . . ?
C1 N1 S1 O2 -35.2(2) . . . . ?
C1 N1 S1 O3 -164.60(18) . . . . ?
C2 C1 N1 C4 -21.2(2) . . . . ?
C2 C1 N1 S1 -170.55(14) . . . . ?
C2 C3 C4 N1 -11.2(2) . . . . ?
C2 C3 C8 C7 1.5(3) . . . . ?
C2 C5 C6 C7 2.0(3) . . . . ?
C2 C5 C6 C9 -175.80(17) . . . . ?
C3 C2 C5 C6 -1.0(3) . . . . ?
C3 C4 N1 C1 20.4(2) . . . . ?
C3 C4 N1 S1 170.70(13) . . . . ?
C4 C3 C8 C7 -177.8(2) . . . . ?
C4 N1 S1 C17 -65.67(17) . . . . ?
C4 N1 S1 O2 177.73(16) . . . . ?
C4 N1 S1 O3 48.28(18) . . . . ?
C5 C2 C3 C4 178.62(17) . . . . ?
C5 C2 C3 C8 -0.8(3) . . . . ?
C5 C6 C7 C8 -1.3(3) . . . . ?
C5 C6 C9 C10 33.5(3) . . . . ?
C5 C6 C9 C14 -149.78(18) . . . . ?
C6 C7 C8 C3 -0.4(3) . . . . ?
C6 C9 C10 C11 175.91(17) . . . . ?
C6 C9 C14 C13 -175.96(17) . . . . ?
C7 C6 C9 C10 -144.31(19) . . . . ?
C7 C6 C9 C14 32.4(3) . . . . ?
C8 C3 C4 N1 168.1(2) . . . . ?
C9 C6 C7 C8 176.57(19) . . . . ?
C9 C10 C11 C12 -0.4(3) . . . . ?
C10 C9 C14 C13 0.9(3) . . . . ?
C10 C11 C12 C13 1.7(3) . . . . ?
C10 C11 C12 O1 -177.86(18) . . . . ?
C11 C12 C13 C14 -1.7(3) . . . . ?
C11 C12 O1 C15 -0.1(3) . . . . ?
C12 C13 C14 C9 0.4(3) . . . . ?
C13 C12 O1 C15 -179.64(19) . . . . ?
C14 C9 C10 C11 -0.9(3) . . . . ?
C16 C15 O1 C12 178.2(2) . . . . ?
C17 C18 C19 C20 -1.0(4) . . . . ?
C18 C17 C22 C21 1.1(3) . . . . ?
C18 C17 S1 N1 -95.49(18) . . . . ?
C18 C17 S1 O2 19.7(2) . . . . ?
C18 C17 S1 O3 151.51(18) . . . . ?
C18 C19 C20 C21 1.6(4) . . . . ?
C18 C19 C20 C23 -179.1(3) . . . . ?
C19 C20 C21 C22 -0.8(4) . . . . ?
C20 C21 C22 C17 -0.5(4) . . . . ?
C22 C17 C18 C19 -0.3(3) . . . . ?
C22 C17 S1 N1 83.04(19) . . . . ?
C22 C17 S1 O2 -161.75(17) . . . . ?
C22 C17 S1 O3 -30.0(2) . . . . ?
C23 C20 C21 C22 179.9(3) . . . . ?
N1 C1 C2 C3 13.4(2) . . . . ?
N1 C1 C2 C5 -166.67(19) . . . . ?
O1 C12 C13 C14 177.90(17) . . . . ?
S1 C17 C18 C19 178.17(18) . . . . ?
S1 C17 C22 C21 -177.42(18) . . . . ?

_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_3af
_database_code_depnum_ccdc_archive 'CCDC 1491619'
_audit_update_record             
;
2017-12-29 deposited with the CCDC.
2018-01-23 downloaded from the CCDC.
;
_audit_creation_date             2017-12-27
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C21 H18 F N O2 S'
_chemical_formula_sum            'C21 H18 F N O2 S'
_chemical_formula_weight         367.42
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H O N S'
_chemical_oxdiff_usercomment     1-41
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'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x, -y-1/2, z-1/2'

_cell_length_a                   20.5689(8)
_cell_length_b                   10.9975(6)
_cell_length_c                   7.9534(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.984(4)
_cell_angle_gamma                90.00
_cell_volume                     1798.03(14)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2167
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      73.3730
_cell_measurement_theta_min      4.5630
_exptl_absorpt_coefficient_mu    1.813
_exptl_absorpt_correction_T_min  0.6702
_exptl_absorpt_correction_T_max  0.7132
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.357
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0250
_diffrn_reflns_av_unetI/netI     0.0364
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            6155
_diffrn_reflns_theta_full        67.07
_diffrn_reflns_theta_max         67.07
_diffrn_reflns_theta_min         4.30
_diffrn_ambient_temperature      294(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            AtlasS2
_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  -30.00    4.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.5455   38.0000  -90.0000 34

#__ type_ start__ end____ width___ exp.time_
  2 omega  -42.00   34.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.5455   38.0000   30.0000 76

#__ type_ start__ end____ width___ exp.time_
  3 omega -112.00   -8.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.5455  -77.0000  -60.0000 104

#__ type_ start__ end____ width___ exp.time_
  4 omega  105.00  175.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      107.1410  125.0000  -30.0000 70

#__ type_ start__ end____ width___ exp.time_
  5 omega   90.00  159.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      107.1410   45.0000 -180.0000 69

#__ type_ start__ end____ width___ exp.time_
  6 omega   43.00   69.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      107.1410  -30.0000  -30.0000 26

#__ type_ start__ end____ width___ exp.time_
  7 omega   37.00   95.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      107.1410  -45.0000   30.0000 58

#__ type_ start__ end____ width___ exp.time_
  8 omega   80.00  109.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      107.1410 -125.0000  -30.0000 29

#__ type_ start__ end____ width___ exp.time_
  9 omega   42.00   68.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      107.1410 -125.0000  -30.0000 26

#__ type_ start__ end____ width___ exp.time_
 10 omega   35.00  138.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      107.1410  -77.0000  -60.0000 103

#__ type_ start__ end____ width___ exp.time_
 11 omega   37.00   73.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      107.1410  -45.0000   90.0000 36
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_orient_matrix_UB_11      0.0650050000
_diffrn_orient_matrix_UB_12      -0.0691015000
_diffrn_orient_matrix_UB_13      -0.0061775000
_diffrn_orient_matrix_UB_21      0.0336933000
_diffrn_orient_matrix_UB_22      0.1166096000
_diffrn_orient_matrix_UB_23      -0.0593360000
_diffrn_orient_matrix_UB_31      0.0157937000
_diffrn_orient_matrix_UB_32      0.0352840000
_diffrn_orient_matrix_UB_33      0.1845481000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2454
_reflns_number_total             3201
_reflns_odcompleteness_completeness 99.79
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_refine_diff_density_max         0.205
_refine_diff_density_min         -0.267
_refine_diff_density_rms         0.071
_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     236
_refine_ls_number_reflns         3201
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0603
_refine_ls_R_factor_gt           0.0414
_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     
'calc w=1/[σ²(Fo²)+(0.0676P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1070
_refine_ls_wR_factor_ref         0.1312
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_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:
 C1(H1A,H1B), C4(H4A,H4B)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C7(H7), C8(H8), C10(H10), C11(H11), C13(H13), C14(H14), C16(H16),
 C17(H17), C19(H19), C20(H20)
2.c Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
C1 C 0.29098(11) 0.7811(2) 0.2929(3) 0.0547(5) Uani 1 d . . .
H1A H 0.3067 0.8187 0.1917 0.066 Uiso 1 calc . . R
H1B H 0.3229 0.7925 0.3842 0.066 Uiso 1 calc . . R
C2 C 0.22561(10) 0.8306(2) 0.3370(3) 0.0470(5) Uani 1 d . . .
C3 C 0.18198(10) 0.7373(2) 0.3626(3) 0.0494(5) Uani 1 d . . .
C4 C 0.21311(11) 0.6162(2) 0.3360(3) 0.0570(6) Uani 1 d . . .
H4A H 0.2193 0.5722 0.4411 0.068 Uiso 1 calc . . R
H4B H 0.1876 0.5668 0.2571 0.068 Uiso 1 calc . . R
C5 C 0.20735(10) 0.9512(2) 0.3527(3) 0.0485(5) Uani 1 d . . .
H5 H 0.2371 1.0131 0.3345 0.058 Uiso 1 calc . . R
C6 C 0.14371(10) 0.9792(2) 0.3961(3) 0.0482(5) Uani 1 d . . .
C7 C 0.10051(11) 0.8838(2) 0.4238(3) 0.0572(6) Uani 1 d . . .
H7 H 0.0582 0.9016 0.4535 0.069 Uiso 1 calc . . R
C8 C 0.11912(11) 0.7633(2) 0.4082(3) 0.0595(6) Uani 1 d . . .
H8 H 0.0899 0.7009 0.4281 0.071 Uiso 1 calc . . R
C9 C 0.12308(10) 1.1078(2) 0.4099(3) 0.0493(5) Uani 1 d . . .
C10 C 0.16485(11) 1.1950(2) 0.4804(3) 0.0556(6) Uani 1 d . . .
H10 H 0.2055 1.1715 0.5238 0.067 Uiso 1 calc . . R
C11 C 0.14686(13) 1.3163(2) 0.4868(4) 0.0659(6) Uani 1 d . . .
H11 H 0.1749 1.3743 0.5338 0.079 Uiso 1 calc . . R
C12 C 0.08702(13) 1.3487(2) 0.4226(4) 0.0671(7) Uani 1 d . . .
C13 C 0.04343(12) 1.2664(3) 0.3557(4) 0.0668(7) Uani 1 d . . .
H13 H 0.0025 1.2912 0.3156 0.080 Uiso 1 calc . . R
C14 C 0.06171(11) 1.1460(2) 0.3493(3) 0.0580(6) Uani 1 d . . .
H14 H 0.0327 1.0889 0.3039 0.070 Uiso 1 calc . . R
C15 C 0.36275(10) 0.5046(2) 0.4407(3) 0.0542(5) Uani 1 d . . .
C16 C 0.41448(12) 0.5651(3) 0.5194(3) 0.0629(6) Uani 1 d . . .
H16 H 0.4322 0.6338 0.4705 0.076 Uiso 1 calc . . R
C17 C 0.43946(12) 0.5216(3) 0.6718(4) 0.0680(7) Uani 1 d . . .
H17 H 0.4742 0.5622 0.7245 0.082 Uiso 1 calc . . R
C18 C 0.41442(12) 0.4202(3) 0.7478(3) 0.0639(6) Uani 1 d . . .
C19 C 0.36137(13) 0.3637(3) 0.6694(4) 0.0688(7) Uani 1 d . . .
H19 H 0.3426 0.2969 0.7205 0.083 Uiso 1 calc . . R
C20 C 0.33559(12) 0.4047(3) 0.5164(4) 0.0650(6) Uani 1 d . . .
H20 H 0.3002 0.3652 0.4650 0.078 Uiso 1 calc . . R
C21 C 0.44499(16) 0.3690(4) 0.9081(4) 0.0866(9) Uani 1 d . . .
H21A H 0.4908 0.3858 0.9118 0.130 Uiso 1 calc . . GR
H21B H 0.4382 0.2827 0.9112 0.130 Uiso 1 calc . . GR
H21C H 0.4254 0.4060 1.0033 0.130 Uiso 1 calc . . GR
F1 F 0.06940(10) 1.46814(16) 0.4270(3) 0.1018(7) Uani 1 d . . .
N1 N 0.27613(9) 0.65179(19) 0.2660(3) 0.0579(5) Uani 1 d . . .
O1 O 0.38394(9) 0.6149(2) 0.1590(2) 0.0743(5) Uani 1 d . . .
O2 O 0.30241(10) 0.44774(18) 0.1641(3) 0.0762(6) Uani 1 d . . .
S1 S 0.33262(3) 0.55225(6) 0.24089(8) 0.0592(2) Uani 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 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C1 C2 1.503(3) . ?
C1 N1 1.469(3) . ?
C2 C3 1.383(3) . ?
C2 C5 1.385(3) . ?
C3 C4 1.496(3) . ?
C3 C8 1.385(3) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 N1 1.481(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.399(3) . ?
C6 C7 1.397(3) . ?
C6 C9 1.483(3) . ?
C7 H7 0.9300 . ?
C7 C8 1.386(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.392(3) . ?
C9 C14 1.400(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.386(4) . ?
C11 H11 0.9300 . ?
C11 C12 1.363(4) . ?
C12 C13 1.368(4) . ?
C12 F1 1.364(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.378(4) . ?
C14 H14 0.9300 . ?
C15 C16 1.386(3) . ?
C15 C20 1.380(4) . ?
C15 S1 1.765(2) . ?
C16 H16 0.9300 . ?
C16 C17 1.385(4) . ?
C17 H17 0.9300 . ?
C17 C18 1.377(4) . ?
C18 C19 1.385(4) . ?
C18 C21 1.511(4) . ?
C19 H19 0.9300 . ?
C19 C20 1.386(4) . ?
C20 H20 0.9300 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
N1 S1 1.6137(19) . ?
O1 S1 1.436(2) . ?
O2 S1 1.433(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
H1A C1 H1B 109.3 . . ?
C2 C1 H1A 111.4 . . ?
C2 C1 H1B 111.4 . . ?
N1 C1 H1A 111.4 . . ?
N1 C1 H1B 111.4 . . ?
N1 C1 C2 101.63(18) . . ?
C3 C2 C1 110.8(2) . . ?
C3 C2 C5 121.2(2) . . ?
C5 C2 C1 128.0(2) . . ?
C2 C3 C4 110.92(19) . . ?
C2 C3 C8 120.1(2) . . ?
C8 C3 C4 129.0(2) . . ?
C3 C4 H4A 111.4 . . ?
C3 C4 H4B 111.4 . . ?
H4A C4 H4B 109.3 . . ?
N1 C4 C3 101.65(19) . . ?
N1 C4 H4A 111.4 . . ?
N1 C4 H4B 111.4 . . ?
C2 C5 H5 120.3 . . ?
C2 C5 C6 119.4(2) . . ?
C6 C5 H5 120.3 . . ?
C5 C6 C9 120.0(2) . . ?
C7 C6 C5 118.7(2) . . ?
C7 C6 C9 121.30(19) . . ?
C6 C7 H7 119.2 . . ?
C8 C7 C6 121.6(2) . . ?
C8 C7 H7 119.2 . . ?
C3 C8 C7 118.9(2) . . ?
C3 C8 H8 120.5 . . ?
C7 C8 H8 120.5 . . ?
C10 C9 C6 120.86(19) . . ?
C10 C9 C14 118.0(2) . . ?
C14 C9 C6 121.2(2) . . ?
C9 C10 H10 119.5 . . ?
C11 C10 C9 121.1(2) . . ?
C11 C10 H10 119.5 . . ?
C10 C11 H11 120.8 . . ?
C12 C11 C10 118.4(3) . . ?
C12 C11 H11 120.8 . . ?
C11 C12 C13 123.0(2) . . ?
C11 C12 F1 118.6(3) . . ?
F1 C12 C13 118.4(2) . . ?
C12 C13 H13 120.9 . . ?
C12 C13 C14 118.3(2) . . ?
C14 C13 H13 120.9 . . ?
C9 C14 H14 119.4 . . ?
C13 C14 C9 121.3(2) . . ?
C13 C14 H14 119.4 . . ?
C16 C15 S1 120.3(2) . . ?
C20 C15 C16 120.1(2) . . ?
C20 C15 S1 119.61(18) . . ?
C15 C16 H16 120.5 . . ?
C17 C16 C15 119.0(3) . . ?
C17 C16 H16 120.5 . . ?
C16 C17 H17 119.0 . . ?
C18 C17 C16 122.0(2) . . ?
C18 C17 H17 119.0 . . ?
C17 C18 C19 117.8(3) . . ?
C17 C18 C21 121.4(3) . . ?
C19 C18 C21 120.8(3) . . ?
C18 C19 H19 119.3 . . ?
C18 C19 C20 121.4(3) . . ?
C20 C19 H19 119.3 . . ?
C15 C20 C19 119.6(2) . . ?
C15 C20 H20 120.2 . . ?
C19 C20 H20 120.2 . . ?
C18 C21 H21A 109.5 . . ?
C18 C21 H21B 109.5 . . ?
C18 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C1 N1 C4 112.44(19) . . ?
C1 N1 S1 121.86(15) . . ?
C4 N1 S1 120.68(17) . . ?
N1 S1 C15 108.79(11) . . ?
O1 S1 C15 108.07(12) . . ?
O1 S1 N1 105.92(12) . . ?
O2 S1 C15 106.20(12) . . ?
O2 S1 N1 107.06(11) . . ?
O2 S1 O1 120.42(13) . . ?

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
C1 C2 C3 C4 -0.8(3) . . . . ?
C1 C2 C3 C8 178.6(2) . . . . ?
C1 C2 C5 C6 -179.6(2) . . . . ?
C1 N1 S1 C15 84.4(2) . . . . ?
C1 N1 S1 O1 -31.6(2) . . . . ?
C1 N1 S1 O2 -161.2(2) . . . . ?
C2 C1 N1 C4 -16.0(2) . . . . ?
C2 C1 N1 S1 -171.03(16) . . . . ?
C2 C3 C4 N1 -8.7(2) . . . . ?
C2 C3 C8 C7 1.5(4) . . . . ?
C2 C5 C6 C7 0.5(3) . . . . ?
C2 C5 C6 C9 -178.77(19) . . . . ?
C3 C2 C5 C6 0.4(3) . . . . ?
C3 C4 N1 C1 15.6(2) . . . . ?
C3 C4 N1 S1 170.96(16) . . . . ?
C4 C3 C8 C7 -179.2(2) . . . . ?
C4 N1 S1 C15 -68.6(2) . . . . ?
C4 N1 S1 O1 175.41(18) . . . . ?
C4 N1 S1 O2 45.7(2) . . . . ?
C5 C2 C3 C4 179.2(2) . . . . ?
C5 C2 C3 C8 -1.4(3) . . . . ?
C5 C6 C7 C8 -0.4(4) . . . . ?
C5 C6 C9 C10 -39.2(3) . . . . ?
C5 C6 C9 C14 139.3(2) . . . . ?
C6 C7 C8 C3 -0.6(4) . . . . ?
C6 C9 C10 C11 177.1(2) . . . . ?
C6 C9 C14 C13 -177.3(2) . . . . ?
C7 C6 C9 C10 141.5(2) . . . . ?
C7 C6 C9 C14 -40.0(3) . . . . ?
C8 C3 C4 N1 172.0(2) . . . . ?
C9 C6 C7 C8 178.9(2) . . . . ?
C9 C10 C11 C12 0.1(4) . . . . ?
C10 C9 C14 C13 1.3(4) . . . . ?
C10 C11 C12 C13 1.5(5) . . . . ?
C10 C11 C12 F1 -179.3(3) . . . . ?
C11 C12 C13 C14 -1.7(4) . . . . ?
C12 C13 C14 C9 0.2(4) . . . . ?
C14 C9 C10 C11 -1.5(4) . . . . ?
C15 C16 C17 C18 -0.1(4) . . . . ?
C16 C15 C20 C19 -1.5(4) . . . . ?
C16 C15 S1 N1 -90.1(2) . . . . ?
C16 C15 S1 O1 24.5(2) . . . . ?
C16 C15 S1 O2 155.0(2) . . . . ?
C16 C17 C18 C19 -2.0(4) . . . . ?
C16 C17 C18 C21 175.9(3) . . . . ?
C17 C18 C19 C20 2.4(4) . . . . ?
C18 C19 C20 C15 -0.6(4) . . . . ?
C20 C15 C16 C17 1.9(4) . . . . ?
C20 C15 S1 N1 91.6(2) . . . . ?
C20 C15 S1 O1 -153.8(2) . . . . ?
C20 C15 S1 O2 -23.3(2) . . . . ?
C21 C18 C19 C20 -175.5(3) . . . . ?
F1 C12 C13 C14 179.1(3) . . . . ?
N1 C1 C2 C3 10.0(2) . . . . ?
N1 C1 C2 C5 -170.0(2) . . . . ?
S1 C15 C16 C17 -176.5(2) . . . . ?
S1 C15 C20 C19 176.8(2) . . . . ?

_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_3ba
_database_code_depnum_ccdc_archive 'CCDC 1491622'
_audit_update_record             
;
2017-12-29 deposited with the CCDC.
2018-01-23 downloaded from the CCDC.
;
_audit_creation_date             2017-12-27
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C20 H16 Cl N O2 S'
_chemical_formula_sum            'C20 H16 Cl N O2 S'
_chemical_formula_weight         369.85
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H O N S'
_chemical_oxdiff_usercomment     1-95
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'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, -z'

_cell_length_a                   7.5142(2)
_cell_length_b                   12.7251(4)
_cell_length_c                   18.0220(5)
_cell_angle_alpha                88.481(2)
_cell_angle_beta                 84.657(2)
_cell_angle_gamma                89.958(2)
_cell_volume                     1715.15(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6983
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      73.6600
_cell_measurement_theta_min      4.9200
_exptl_absorpt_coefficient_mu    3.218
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.57132
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.432
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.2
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0330
_diffrn_reflns_av_unetI/netI     0.0429
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            11482
_diffrn_reflns_theta_full        73.78
_diffrn_reflns_theta_max         73.78
_diffrn_reflns_theta_min         3.47
_diffrn_ambient_temperature      294(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3031
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.963
_diffrn_measured_fraction_theta_max 0.963
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -35.00   15.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.5455   38.0000  -60.0000 50

#__ type_ start__ end____ width___ exp.time_
  2 omega  -48.00   33.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.5455   38.0000    0.0000 81

#__ type_ start__ end____ width___ exp.time_
  3 omega   39.00   81.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.5455  -99.0000  -30.0000 42

#__ type_ start__ end____ width___ exp.time_
  4 omega   72.00   97.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.5455 -125.0000    0.0000 25

#__ type_ start__ end____ width___ exp.time_
  5 omega   42.00   98.00   1.0000    2.4200
omega____ theta____ kappa____ phi______ frames
    -      107.1410  -45.0000   60.0000 56

#__ type_ start__ end____ width___ exp.time_
  6 omega   57.00   90.00   1.0000    2.4200
omega____ theta____ kappa____ phi______ frames
    -      107.1410  -30.0000  -30.0000 33

#__ type_ start__ end____ width___ exp.time_
  7 omega   49.00   84.00   1.0000    2.4200
omega____ theta____ kappa____ phi______ frames
    -      107.1410  -45.0000  -30.0000 35

#__ type_ start__ end____ width___ exp.time_
  8 omega   52.00  102.00   1.0000    2.4200
omega____ theta____ kappa____ phi______ frames
    -      107.1410  -95.0000  -30.0000 50

#__ type_ start__ end____ width___ exp.time_
  9 omega   90.00  120.00   1.0000    2.4200
omega____ theta____ kappa____ phi______ frames
    -      107.1410 -125.0000  -60.0000 30

#__ type_ start__ end____ width___ exp.time_
 10 omega   41.00  108.00   1.0000    2.4200
omega____ theta____ kappa____ phi______ frames
    -      107.1410  -95.0000   90.0000 67

#__ type_ start__ end____ width___ exp.time_
 11 omega   52.00  136.00   1.0000    2.4200
omega____ theta____ kappa____ phi______ frames
    -      107.1410  -77.0000  150.0000 84

#__ type_ start__ end____ width___ exp.time_
 12 omega   56.00  160.00   1.0000    2.4200
omega____ theta____ kappa____ phi______ frames
    -      107.1410   15.0000  150.0000 104

#__ type_ start__ end____ width___ exp.time_
 13 omega   94.00  131.00   1.0000    2.4200
omega____ theta____ kappa____ phi______ frames
    -      107.1410  125.0000    0.0000 37

#__ type_ start__ end____ width___ exp.time_
 14 omega   83.00  109.00   1.0000    2.4200
omega____ theta____ kappa____ phi______ frames
    -      107.1410   45.0000    0.0000 26

#__ type_ start__ end____ width___ exp.time_
 15 omega  130.00  162.00   1.0000    2.4200
omega____ theta____ kappa____ phi______ frames
    -      107.1410   45.0000    0.0000 32

#__ type_ start__ end____ width___ exp.time_
 16 omega   39.00   68.00   1.0000    2.4200
omega____ theta____ kappa____ phi______ frames
    -      107.1410  -30.0000  -60.0000 29

#__ type_ start__ end____ width___ exp.time_
 17 omega   37.00   88.00   1.0000    2.4200
omega____ theta____ kappa____ phi______ frames
    -      107.1410  -45.0000 -120.0000 51

#__ type_ start__ end____ width___ exp.time_
 18 omega   35.00   84.00   1.0000    2.4200
omega____ theta____ kappa____ phi______ frames
    -      107.1410  -30.0000 -180.0000 49

#__ type_ start__ end____ width___ exp.time_
 19 omega   32.00   90.00   1.0000    2.4200
omega____ theta____ kappa____ phi______ frames
    -      107.1410  -30.0000  120.0000 58

#__ type_ start__ end____ width___ exp.time_
 20 omega  -68.00   29.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.5455   57.0000 -150.0000 97

#__ type_ start__ end____ width___ exp.time_
 21 omega -111.00  -21.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.5455  -57.0000   60.0000 90
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0722086000
_diffrn_orient_matrix_UB_12      0.0554796000
_diffrn_orient_matrix_UB_13      0.0660098000
_diffrn_orient_matrix_UB_21      0.0292259000
_diffrn_orient_matrix_UB_22      -0.1075667000
_diffrn_orient_matrix_UB_23      0.0381914000
_diffrn_orient_matrix_UB_31      0.1906102000
_diffrn_orient_matrix_UB_32      -0.0042970000
_diffrn_orient_matrix_UB_33      -0.0395026000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                5953
_reflns_number_total             6691
_reflns_odcompleteness_completeness 99.87
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.248
_refine_diff_density_min         -0.616
_refine_diff_density_rms         0.098
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     451
_refine_ls_number_reflns         6691
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0506
_refine_ls_R_factor_gt           0.0465
_refine_ls_restrained_S_all      1.045
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0716P)²+0.2538P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1196
_refine_ls_wR_factor_ref         0.1257
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C4(H4A,H4B), C21(H21A,H21B), C24(H24A,H24B)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C7(H7), C8(H8), C10(H10), C11(H11), C12(H12), C13(H13), C14(H14),
 C16(H16), C17(H17), C18(H18), C19(H19), C25(H25), C27(H27), C28(H28), C30(H30),
  C31(H31), C32(H32), C33(H33), C34(H34), C36(H36), C37(H37), C38(H38), C39(H39)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
C1 C 0.6648(3) 0.29632(15) 0.30697(10) 0.0432(4) Uani 1 d . . .
H1A H 0.7626 0.2486 0.2936 0.052 Uiso 1 calc . . R
H1B H 0.5541 0.2567 0.3152 0.052 Uiso 1 calc . . R
C2 C 0.6985(2) 0.35864(15) 0.37418(10) 0.0386(4) Uani 1 d . . .
C3 C 0.7394(3) 0.46172(16) 0.35313(11) 0.0448(4) Uani 1 d . . .
C4 C 0.7368(3) 0.47894(17) 0.27087(12) 0.0526(5) Uani 1 d . . .
H4A H 0.6657 0.5399 0.2593 0.063 Uiso 1 calc . . R
H4B H 0.8566 0.4873 0.2463 0.063 Uiso 1 calc . . R
C5 C 0.6984(3) 0.32422(15) 0.44780(10) 0.0405(4) Uani 1 d . . .
H5 H 0.6702 0.2548 0.4614 0.049 Uiso 1 calc . . R
C6 C 0.7413(3) 0.39533(16) 0.50145(11) 0.0441(4) Uani 1 d . . .
C7 C 0.7815(4) 0.49891(18) 0.47912(13) 0.0585(6) Uani 1 d . . .
H7 H 0.8081 0.5466 0.5147 0.070 Uiso 1 calc . . R
C8 C 0.7828(4) 0.53303(17) 0.40512(13) 0.0597(6) Uani 1 d . . .
H8 H 0.8122 0.6021 0.3910 0.072 Uiso 1 calc . . R
C9 C 0.7546(3) 0.36130(17) 0.58063(11) 0.0455(4) Uani 1 d . . .
C10 C 0.8263(3) 0.26440(18) 0.59843(12) 0.0512(5) Uani 1 d . . .
H10 H 0.8581 0.2175 0.5608 0.061 Uiso 1 calc . . R
C11 C 0.8512(3) 0.2366(2) 0.67201(14) 0.0616(6) Uani 1 d . . .
H11 H 0.8998 0.1714 0.6830 0.074 Uiso 1 calc . . R
C12 C 0.8045(3) 0.3049(2) 0.72874(13) 0.0659(7) Uani 1 d . . .
H12 H 0.8226 0.2863 0.7777 0.079 Uiso 1 calc . . R
C13 C 0.7310(4) 0.4008(2) 0.71211(13) 0.0665(7) Uani 1 d . . .
H13 H 0.6981 0.4470 0.7501 0.080 Uiso 1 calc . . R
C14 C 0.7056(3) 0.4291(2) 0.63875(13) 0.0566(5) Uani 1 d . . .
H14 H 0.6554 0.4940 0.6282 0.068 Uiso 1 calc . . R
C15 C 0.8586(2) 0.31111(14) 0.12560(9) 0.0342(3) Uani 1 d . . .
C16 C 0.8863(3) 0.20349(15) 0.11868(10) 0.0404(4) Uani 1 d . . .
H16 H 0.7937 0.1571 0.1339 0.049 Uiso 1 calc . . R
C17 C 1.0492(3) 0.16442(16) 0.08953(11) 0.0486(5) Uani 1 d . . .
H17 H 1.0657 0.0923 0.0851 0.058 Uiso 1 calc . . R
C18 C 1.1870(3) 0.23299(17) 0.06704(11) 0.0489(5) Uani 1 d . . .
H18 H 1.2971 0.2069 0.0481 0.059 Uiso 1 calc . . R
C19 C 1.1622(3) 0.34019(17) 0.07255(11) 0.0479(4) Uani 1 d . . .
H19 H 1.2556 0.3859 0.0570 0.058 Uiso 1 calc . . R
C20 C 0.9987(3) 0.37996(15) 0.10111(10) 0.0396(4) Uani 1 d . . .
C21 C 0.6619(3) 0.80677(17) 0.29568(11) 0.0504(5) Uani 1 d . . .
H21A H 0.7355 0.7442 0.2916 0.060 Uiso 1 calc . . R
H21B H 0.5370 0.7867 0.2975 0.060 Uiso 1 calc . . R
C22 C 0.6983(2) 0.86856(15) 0.36254(10) 0.0390(4) Uani 1 d . . .
C23 C 0.7555(3) 0.96916(15) 0.34105(11) 0.0409(4) Uani 1 d . . .
C24 C 0.7629(3) 0.98670(15) 0.25844(11) 0.0483(5) Uani 1 d . . .
H24A H 0.6794 1.0407 0.2452 0.058 Uiso 1 calc . . R
H24B H 0.8823 1.0059 0.2374 0.058 Uiso 1 calc . . R
C25 C 0.6890(3) 0.83456(15) 0.43646(11) 0.0414(4) Uani 1 d . . .
H25 H 0.6496 0.7669 0.4501 0.050 Uiso 1 calc . . R
C26 C 0.7392(3) 0.90283(16) 0.49025(11) 0.0419(4) Uani 1 d . . .
C27 C 0.7933(3) 1.00501(16) 0.46796(12) 0.0492(5) Uani 1 d . . .
H27 H 0.8237 1.0515 0.5037 0.059 Uiso 1 calc . . R
C28 C 0.8026(3) 1.03874(15) 0.39384(12) 0.0487(5) Uani 1 d . . .
H28 H 0.8396 1.1067 0.3799 0.058 Uiso 1 calc . . R
C29 C 0.7513(3) 0.86604(18) 0.56874(11) 0.0465(4) Uani 1 d . . .
C30 C 0.8167(3) 0.76640(19) 0.58425(12) 0.0531(5) Uani 1 d . . .
H30 H 0.8453 0.7210 0.5453 0.064 Uiso 1 calc . . R
C31 C 0.8404(4) 0.7331(3) 0.65708(15) 0.0684(7) Uani 1 d . . .
H31 H 0.8830 0.6659 0.6664 0.082 Uiso 1 calc . . R
C32 C 0.8004(4) 0.8000(3) 0.71502(14) 0.0774(9) Uani 1 d . . .
H32 H 0.8170 0.7785 0.7636 0.093 Uiso 1 calc . . R
C33 C 0.7360(4) 0.8988(3) 0.70073(14) 0.0786(9) Uani 1 d . . .
H33 H 0.7092 0.9440 0.7399 0.094 Uiso 1 calc . . R
C34 C 0.7102(3) 0.9321(2) 0.62832(13) 0.0615(6) Uani 1 d . . .
H34 H 0.6652 0.9990 0.6197 0.074 Uiso 1 calc . . R
C35 C 0.5748(2) 0.80430(14) 0.11423(9) 0.0338(3) Uani 1 d . . .
C36 C 0.5487(3) 0.69849(15) 0.10179(10) 0.0406(4) Uani 1 d . . .
H36 H 0.6337 0.6493 0.1138 0.049 Uiso 1 calc . . R
C37 C 0.3950(3) 0.66617(17) 0.07127(11) 0.0477(4) Uani 1 d . . .
H37 H 0.3777 0.5954 0.0625 0.057 Uiso 1 calc . . R
C38 C 0.2687(3) 0.73872(18) 0.05405(11) 0.0492(5) Uani 1 d . . .
H38 H 0.1657 0.7165 0.0341 0.059 Uiso 1 calc . . R
C39 C 0.2932(3) 0.84451(18) 0.06605(11) 0.0472(5) Uani 1 d . . .
H39 H 0.2074 0.8931 0.0539 0.057 Uiso 1 calc . . R
C40 C 0.4463(3) 0.87783(15) 0.09625(10) 0.0382(4) Uani 1 d . . .
Cl1 Cl 0.97818(8) 0.51569(4) 0.10385(3) 0.05965(17) Uani 1 d . . .
Cl2 Cl 0.46957(8) 1.01089(4) 0.11102(3) 0.05428(15) Uani 1 d . . .
N1 N 0.6532(2) 0.38079(13) 0.24965(9) 0.0425(4) Uani 1 d . . .
N2 N 0.7105(3) 0.88243(13) 0.23389(9) 0.0470(4) Uani 1 d . . .
O1 O 0.5326(2) 0.25825(12) 0.16475(8) 0.0501(3) Uani 1 d . . .
O2 O 0.5912(2) 0.44381(12) 0.12460(8) 0.0530(4) Uani 1 d . . .
O3 O 0.8732(2) 0.74469(13) 0.15849(10) 0.0582(4) Uani 1 d . . .
O4 O 0.8576(2) 0.92683(12) 0.10938(9) 0.0527(4) Uani 1 d . . .
S1 S 0.64178(6) 0.35067(4) 0.16317(2) 0.03839(12) Uani 1 d . . .
S2 S 0.77497(6) 0.84016(4) 0.15174(2) 0.04003(13) Uani 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 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C1 C2 1.506(3) . ?
C1 N1 1.479(2) . ?
C2 C3 1.383(3) . ?
C2 C5 1.386(3) . ?
C3 C4 1.495(3) . ?
C3 C8 1.382(3) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 N1 1.474(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.401(3) . ?
C6 C7 1.393(3) . ?
C6 C9 1.492(3) . ?
C7 H7 0.9300 . ?
C7 C8 1.391(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.387(3) . ?
C9 C14 1.397(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.393(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.379(4) . ?
C12 H12 0.9300 . ?
C12 C13 1.377(4) . ?
C13 H13 0.9300 . ?
C13 C14 1.391(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.392(3) . ?
C15 C20 1.402(3) . ?
C15 S1 1.7827(18) . ?
C16 H16 0.9300 . ?
C16 C17 1.384(3) . ?
C17 H17 0.9300 . ?
C17 C18 1.379(3) . ?
C18 H18 0.9300 . ?
C18 C19 1.382(3) . ?
C19 H19 0.9300 . ?
C19 C20 1.388(3) . ?
C20 Cl1 1.7355(19) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C21 C22 1.502(3) . ?
C21 N2 1.472(3) . ?
C22 C23 1.384(3) . ?
C22 C25 1.385(3) . ?
C23 C24 1.496(3) . ?
C23 C28 1.386(3) . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C24 N2 1.475(2) . ?
C25 H25 0.9300 . ?
C25 C26 1.397(3) . ?
C26 C27 1.400(3) . ?
C26 C29 1.489(3) . ?
C27 H27 0.9300 . ?
C27 C28 1.388(3) . ?
C28 H28 0.9300 . ?
C29 C30 1.391(3) . ?
C29 C34 1.393(3) . ?
C30 H30 0.9300 . ?
C30 C31 1.395(3) . ?
C31 H31 0.9300 . ?
C31 C32 1.376(4) . ?
C32 H32 0.9300 . ?
C32 C33 1.373(5) . ?
C33 H33 0.9300 . ?
C33 C34 1.392(4) . ?
C34 H34 0.9300 . ?
C35 C36 1.388(3) . ?
C35 C40 1.398(2) . ?
C35 S2 1.7705(18) . ?
C36 H36 0.9300 . ?
C36 C37 1.392(3) . ?
C37 H37 0.9300 . ?
C37 C38 1.374(3) . ?
C38 H38 0.9300 . ?
C38 C39 1.384(3) . ?
C39 H39 0.9300 . ?
C39 C40 1.389(3) . ?
C40 Cl2 1.7324(19) . ?
N1 S1 1.6248(16) . ?
N2 S2 1.6200(17) . ?
O1 S1 1.4326(15) . ?
O2 S1 1.4272(15) . ?
O3 S2 1.4295(15) . ?
O4 S2 1.4326(15) . ?

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
H1A C1 H1B 109.3 . . ?
C2 C1 H1A 111.5 . . ?
C2 C1 H1B 111.5 . . ?
N1 C1 H1A 111.5 . . ?
N1 C1 H1B 111.5 . . ?
N1 C1 C2 101.45(15) . . ?
C3 C2 C1 110.20(17) . . ?
C3 C2 C5 121.09(17) . . ?
C5 C2 C1 128.67(18) . . ?
C2 C3 C4 111.22(17) . . ?
C8 C3 C2 120.7(2) . . ?
C8 C3 C4 128.1(2) . . ?
C3 C4 H4A 111.5 . . ?
C3 C4 H4B 111.5 . . ?
H4A C4 H4B 109.3 . . ?
N1 C4 C3 101.52(16) . . ?
N1 C4 H4A 111.5 . . ?
N1 C4 H4B 111.5 . . ?
C2 C5 H5 120.4 . . ?
C2 C5 C6 119.17(18) . . ?
C6 C5 H5 120.4 . . ?
C5 C6 C9 121.58(19) . . ?
C7 C6 C5 118.82(19) . . ?
C7 C6 C9 119.52(18) . . ?
C6 C7 H7 119.1 . . ?
C8 C7 C6 121.9(2) . . ?
C8 C7 H7 119.1 . . ?
C3 C8 C7 118.4(2) . . ?
C3 C8 H8 120.8 . . ?
C7 C8 H8 120.8 . . ?
C10 C9 C6 121.10(18) . . ?
C10 C9 C14 118.0(2) . . ?
C14 C9 C6 120.7(2) . . ?
C9 C10 H10 119.6 . . ?
C9 C10 C11 120.8(2) . . ?
C11 C10 H10 119.6 . . ?
C10 C11 H11 119.7 . . ?
C12 C11 C10 120.6(2) . . ?
C12 C11 H11 119.7 . . ?
C11 C12 H12 120.3 . . ?
C13 C12 C11 119.3(2) . . ?
C13 C12 H12 120.3 . . ?
C12 C13 H13 119.8 . . ?
C12 C13 C14 120.4(2) . . ?
C14 C13 H13 119.8 . . ?
C9 C14 H14 119.6 . . ?
C13 C14 C9 120.9(2) . . ?
C13 C14 H14 119.6 . . ?
C16 C15 C20 118.60(17) . . ?
C16 C15 S1 116.45(14) . . ?
C20 C15 S1 124.92(14) . . ?
C15 C16 H16 119.4 . . ?
C17 C16 C15 121.13(18) . . ?
C17 C16 H16 119.4 . . ?
C16 C17 H17 120.2 . . ?
C18 C17 C16 119.62(18) . . ?
C18 C17 H17 120.2 . . ?
C17 C18 H18 119.8 . . ?
C17 C18 C19 120.34(19) . . ?
C19 C18 H18 119.8 . . ?
C18 C19 H19 119.8 . . ?
C18 C19 C20 120.4(2) . . ?
C20 C19 H19 119.8 . . ?
C15 C20 Cl1 122.92(15) . . ?
C19 C20 C15 119.93(18) . . ?
C19 C20 Cl1 117.14(15) . . ?
H21A C21 H21B 109.2 . . ?
C22 C21 H21A 111.3 . . ?
C22 C21 H21B 111.3 . . ?
N2 C21 H21A 111.3 . . ?
N2 C21 H21B 111.3 . . ?
N2 C21 C22 102.11(16) . . ?
C23 C22 C21 110.53(17) . . ?
C23 C22 C25 121.24(17) . . ?
C25 C22 C21 128.15(18) . . ?
C22 C23 C24 111.88(16) . . ?
C22 C23 C28 120.22(18) . . ?
C28 C23 C24 127.87(18) . . ?
C23 C24 H24A 111.5 . . ?
C23 C24 H24B 111.5 . . ?
H24A C24 H24B 109.3 . . ?
N2 C24 C23 101.58(15) . . ?
N2 C24 H24A 111.5 . . ?
N2 C24 H24B 111.5 . . ?
C22 C25 H25 120.3 . . ?
C22 C25 C26 119.37(18) . . ?
C26 C25 H25 120.3 . . ?
C25 C26 C27 118.76(18) . . ?
C25 C26 C29 121.20(19) . . ?
C27 C26 C29 119.82(18) . . ?
C26 C27 H27 119.2 . . ?
C28 C27 C26 121.66(18) . . ?
C28 C27 H27 119.2 . . ?
C23 C28 C27 118.72(19) . . ?
C23 C28 H28 120.6 . . ?
C27 C28 H28 120.6 . . ?
C30 C29 C26 120.46(18) . . ?
C30 C29 C34 117.9(2) . . ?
C34 C29 C26 121.5(2) . . ?
C29 C30 H30 119.3 . . ?
C29 C30 C31 121.3(2) . . ?
C31 C30 H30 119.3 . . ?
C30 C31 H31 120.1 . . ?
C32 C31 C30 119.9(3) . . ?
C32 C31 H31 120.1 . . ?
C31 C32 H32 120.2 . . ?
C33 C32 C31 119.6(2) . . ?
C33 C32 H32 120.2 . . ?
C32 C33 H33 119.6 . . ?
C32 C33 C34 120.8(3) . . ?
C34 C33 H33 119.6 . . ?
C29 C34 H34 119.8 . . ?
C33 C34 C29 120.5(3) . . ?
C33 C34 H34 119.8 . . ?
C36 C35 C40 119.83(17) . . ?
C36 C35 S2 117.47(14) . . ?
C40 C35 S2 122.69(14) . . ?
C35 C36 H36 120.1 . . ?
C35 C36 C37 119.85(18) . . ?
C37 C36 H36 120.1 . . ?
C36 C37 H37 120.0 . . ?
C38 C37 C36 120.07(19) . . ?
C38 C37 H37 120.0 . . ?
C37 C38 H38 119.7 . . ?
C37 C38 C39 120.67(19) . . ?
C39 C38 H38 119.7 . . ?
C38 C39 H39 120.1 . . ?
C38 C39 C40 119.82(19) . . ?
C40 C39 H39 120.1 . . ?
C35 C40 Cl2 122.23(15) . . ?
C39 C40 C35 119.76(18) . . ?
C39 C40 Cl2 118.01(15) . . ?
C1 N1 S1 119.75(13) . . ?
C4 N1 C1 111.71(15) . . ?
C4 N1 S1 122.27(13) . . ?
C21 N2 C24 113.77(16) . . ?
C21 N2 S2 119.80(14) . . ?
C24 N2 S2 122.11(14) . . ?
N1 S1 C15 108.19(8) . . ?
O1 S1 C15 105.63(9) . . ?
O1 S1 N1 106.07(9) . . ?
O2 S1 C15 109.20(9) . . ?
O2 S1 N1 107.07(9) . . ?
O2 S1 O1 120.18(10) . . ?
N2 S2 C35 104.58(9) . . ?
O3 S2 C35 105.60(9) . . ?
O3 S2 N2 109.69(10) . . ?
O3 S2 O4 118.97(10) . . ?
O4 S2 C35 109.94(9) . . ?
O4 S2 N2 107.19(9) . . ?

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
C1 C2 C3 C4 0.2(2) . . . . ?
C1 C2 C3 C8 -177.3(2) . . . . ?
C1 C2 C5 C6 177.2(2) . . . . ?
C1 N1 S1 C15 -75.43(17) . . . . ?
C1 N1 S1 O1 37.51(18) . . . . ?
C1 N1 S1 O2 166.99(15) . . . . ?
C2 C1 N1 C4 19.6(2) . . . . ?
C2 C1 N1 S1 172.41(13) . . . . ?
C2 C3 C4 N1 11.4(2) . . . . ?
C2 C3 C8 C7 -1.0(4) . . . . ?
C2 C5 C6 C7 0.5(3) . . . . ?
C2 C5 C6 C9 -176.12(18) . . . . ?
C3 C2 C5 C6 -0.3(3) . . . . ?
C3 C4 N1 C1 -19.5(2) . . . . ?
C3 C4 N1 S1 -171.51(14) . . . . ?
C4 C3 C8 C7 -178.1(2) . . . . ?
C4 N1 S1 C15 74.46(18) . . . . ?
C4 N1 S1 O1 -172.60(17) . . . . ?
C4 N1 S1 O2 -43.1(2) . . . . ?
C5 C2 C3 C4 178.05(19) . . . . ?
C5 C2 C3 C8 0.5(3) . . . . ?
C5 C6 C7 C8 -1.1(4) . . . . ?
C5 C6 C9 C10 37.6(3) . . . . ?
C5 C6 C9 C14 -146.6(2) . . . . ?
C6 C7 C8 C3 1.3(4) . . . . ?
C6 C9 C10 C11 174.9(2) . . . . ?
C6 C9 C14 C13 -174.9(2) . . . . ?
C7 C6 C9 C10 -139.0(2) . . . . ?
C7 C6 C9 C14 36.8(3) . . . . ?
C8 C3 C4 N1 -171.3(2) . . . . ?
C9 C6 C7 C8 175.7(2) . . . . ?
C9 C10 C11 C12 0.2(4) . . . . ?
C10 C9 C14 C13 1.1(4) . . . . ?
C10 C11 C12 C13 0.7(4) . . . . ?
C11 C12 C13 C14 -0.6(4) . . . . ?
C12 C13 C14 C9 -0.2(4) . . . . ?
C14 C9 C10 C11 -1.1(3) . . . . ?
C15 C16 C17 C18 0.1(3) . . . . ?
C16 C15 C20 C19 -1.7(3) . . . . ?
C16 C15 C20 Cl1 177.76(14) . . . . ?
C16 C15 S1 N1 102.47(14) . . . . ?
C16 C15 S1 O1 -10.77(16) . . . . ?
C16 C15 S1 O2 -141.32(14) . . . . ?
C16 C17 C18 C19 -0.9(3) . . . . ?
C17 C18 C19 C20 0.3(3) . . . . ?
C18 C19 C20 C15 1.0(3) . . . . ?
C18 C19 C20 Cl1 -178.49(16) . . . . ?
C20 C15 C16 C17 1.1(3) . . . . ?
C20 C15 S1 N1 -79.38(17) . . . . ?
C20 C15 S1 O1 167.38(15) . . . . ?
C20 C15 S1 O2 36.83(18) . . . . ?
C21 C22 C23 C24 0.4(2) . . . . ?
C21 C22 C23 C28 -177.9(2) . . . . ?
C21 C22 C25 C26 176.0(2) . . . . ?
C21 N2 S2 C35 78.56(18) . . . . ?
C21 N2 S2 O3 -34.3(2) . . . . ?
C21 N2 S2 O4 -164.74(17) . . . . ?
C22 C21 N2 C24 -3.5(3) . . . . ?
C22 C21 N2 S2 153.71(15) . . . . ?
C22 C23 C24 N2 -2.4(2) . . . . ?
C22 C23 C28 C27 0.8(3) . . . . ?
C22 C25 C26 C27 1.7(3) . . . . ?
C22 C25 C26 C29 -172.94(18) . . . . ?
C23 C22 C25 C26 -0.4(3) . . . . ?
C23 C24 N2 C21 3.6(2) . . . . ?
C23 C24 N2 S2 -152.93(15) . . . . ?
C24 C23 C28 C27 -177.1(2) . . . . ?
C24 N2 S2 C35 -126.23(17) . . . . ?
C24 N2 S2 O3 120.93(17) . . . . ?
C24 N2 S2 O4 -9.5(2) . . . . ?
C25 C22 C23 C24 177.34(19) . . . . ?
C25 C22 C23 C28 -0.9(3) . . . . ?
C25 C26 C27 C28 -1.8(3) . . . . ?
C25 C26 C29 C30 38.1(3) . . . . ?
C25 C26 C29 C34 -146.6(2) . . . . ?
C26 C27 C28 C23 0.5(3) . . . . ?
C26 C29 C30 C31 175.6(2) . . . . ?
C26 C29 C34 C33 -174.9(2) . . . . ?
C27 C26 C29 C30 -136.4(2) . . . . ?
C27 C26 C29 C34 38.9(3) . . . . ?
C28 C23 C24 N2 175.7(2) . . . . ?
C29 C26 C27 C28 172.9(2) . . . . ?
C29 C30 C31 C32 -0.7(4) . . . . ?
C30 C29 C34 C33 0.6(4) . . . . ?
C30 C31 C32 C33 0.6(4) . . . . ?
C31 C32 C33 C34 0.1(4) . . . . ?
C32 C33 C34 C29 -0.7(4) . . . . ?
C34 C29 C30 C31 0.1(3) . . . . ?
C35 C36 C37 C38 -0.5(3) . . . . ?
C36 C35 C40 C39 0.0(3) . . . . ?
C36 C35 C40 Cl2 179.45(14) . . . . ?
C36 C35 S2 N2 -113.58(15) . . . . ?
C36 C35 S2 O3 2.14(17) . . . . ?
C36 C35 S2 O4 131.64(14) . . . . ?
C36 C37 C38 C39 0.7(3) . . . . ?
C37 C38 C39 C40 -0.4(3) . . . . ?
C38 C39 C40 C35 0.1(3) . . . . ?
C38 C39 C40 Cl2 -179.36(16) . . . . ?
C40 C35 C36 C37 0.2(3) . . . . ?
C40 C35 S2 N2 67.28(16) . . . . ?
C40 C35 S2 O3 -177.00(15) . . . . ?
C40 C35 S2 O4 -47.49(17) . . . . ?
N1 C1 C2 C3 -11.7(2) . . . . ?
N1 C1 C2 C5 170.65(19) . . . . ?
N2 C21 C22 C23 1.8(2) . . . . ?
N2 C21 C22 C25 -174.9(2) . . . . ?
S1 C15 C16 C17 179.40(15) . . . . ?
S1 C15 C20 C19 -179.79(15) . . . . ?
S1 C15 C20 Cl1 -0.4(2) . . . . ?
S2 C35 C36 C37 -178.97(14) . . . . ?
S2 C35 C40 C39 179.14(14) . . . . ?
S2 C35 C40 Cl2 -1.4(2) . . . . ?

_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_3ag
_database_code_depnum_ccdc_archive 'CCDC 1491620'
_audit_update_record             
;
2017-12-29 deposited with the CCDC.
2018-01-23 downloaded from the CCDC.
;
_audit_creation_date             2017-12-27
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C21 H18 Cl N O2 S'
_chemical_formula_sum            'C21 H18 Cl N O2 S'
_chemical_formula_weight         383.87
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H O N 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'
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'
Cl Cl 0.3639 0.7018 '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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, -y, z+1/2'
3 '-x, y+1/2, -z+1/2'
4 'x+1/2, -y+1/2, -z'

_cell_length_a                   7.08143(9)
_cell_length_b                   9.08409(11)
_cell_length_c                   29.0369(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1867.89(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    18135
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      73.6170
_cell_measurement_theta_min      4.8540
_exptl_absorpt_coefficient_mu    2.975
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.37839
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.365
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0701
_diffrn_reflns_av_unetI/netI     0.0232
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            30484
_diffrn_reflns_theta_full        66.99
_diffrn_reflns_theta_max         66.99
_diffrn_reflns_theta_min         5.10
_diffrn_ambient_temperature      294(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3031
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega    2.00   27.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       40.5455  -99.0000  -90.0000 25

#__ type_ start__ end____ width___ exp.time_
  2 omega   34.00   98.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      107.1410  -45.0000 -180.0000 64

#__ type_ start__ end____ width___ exp.time_
  3 omega   25.00   96.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      107.1410  -95.0000 -150.0000 71

#__ type_ start__ end____ width___ exp.time_
  4 omega   36.00   78.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      107.1410  -45.0000  -30.0000 42

#__ type_ start__ end____ width___ exp.time_
  5 omega   55.00   85.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      107.1410  -30.0000   90.0000 30

#__ type_ start__ end____ width___ exp.time_
  6 omega   34.00   77.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       40.5455 -125.0000  150.0000 43

#__ type_ start__ end____ width___ exp.time_
  7 omega  -43.00   14.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.5455   38.0000  150.0000 57

#__ type_ start__ end____ width___ exp.time_
  8 omega   50.00   88.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       40.5455   77.0000  150.0000 38

#__ type_ start__ end____ width___ exp.time_
  9 omega  106.00  177.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      107.1410  125.0000 -150.0000 71

#__ type_ start__ end____ width___ exp.time_
 10 omega -104.00  -19.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -40.7955  -38.0000   60.0000 85

#__ type_ start__ end____ width___ exp.time_
 11 omega  -33.00   -8.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -40.7955  -77.0000  -30.0000 25

#__ type_ start__ end____ width___ exp.time_
 12 omega -120.00   -2.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -40.7955  -19.0000  150.0000 118

#__ type_ start__ end____ width___ exp.time_
 13 omega -107.00  -60.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -40.7955  -77.0000  -30.0000 47

#__ type_ start__ end____ width___ exp.time_
 14 omega  -49.00   33.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -40.7955   38.0000 -120.0000 82

#__ type_ start__ end____ width___ exp.time_
 15 omega    5.00   30.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       40.7955   88.0000  112.0905 25

#__ type_ start__ end____ width___ exp.time_
 16 omega   24.00   95.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       40.7955 -125.0000    0.0000 71

#__ type_ start__ end____ width___ exp.time_
 17 omega    8.00   33.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       42.0000   82.0000  -40.8064 25

#__ type_ start__ end____ width___ exp.time_
 18 omega   18.00   43.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       50.0000   80.0000   36.1259 25

#__ type_ start__ end____ width___ exp.time_
 19 omega   16.00   41.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       50.0000   82.0000   91.7644 25

#__ type_ start__ end____ width___ exp.time_
 20 omega   21.00   47.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   79.0000 -116.3879 26

#__ type_ start__ end____ width___ exp.time_
 21 omega   21.00   46.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   79.0000  156.8730 25

#__ type_ start__ end____ width___ exp.time_
 22 omega   31.00   57.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       58.0000   77.0000  -59.9348 26

#__ type_ start__ end____ width___ exp.time_
 23 omega   29.00   64.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       58.0000   75.0000 -146.2639 35

#__ type_ start__ end____ width___ exp.time_
 24 omega  109.00  134.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       58.0000   77.0000  -59.9348 25

#__ type_ start__ end____ width___ exp.time_
 25 omega   30.00   70.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       62.0000   75.0000  -89.0240 40

#__ type_ start__ end____ width___ exp.time_
 26 omega   33.00   77.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       66.0000   77.0000  174.3629 44

#__ type_ start__ end____ width___ exp.time_
 27 omega  100.00  126.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       66.0000   77.0000  102.2897 26

#__ type_ start__ end____ width___ exp.time_
 28 omega   34.00   82.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       66.0000   76.0000  -26.5652 48

#__ type_ start__ end____ width___ exp.time_
 29 omega   33.00   59.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       66.0000   77.0000  102.2897 26

#__ type_ start__ end____ width___ exp.time_
 30 omega  110.00  140.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       66.0000   77.0000  174.3629 30

#__ type_ start__ end____ width___ exp.time_
 31 omega   38.00   79.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       70.0000   77.0000  115.5086 41

#__ type_ start__ end____ width___ exp.time_
 32 omega  118.00  144.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       70.0000   75.0000   49.9610 26

#__ type_ start__ end____ width___ exp.time_
 33 omega   38.00   67.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       70.0000   75.0000   49.9610 29

#__ type_ start__ end____ width___ exp.time_
 34 omega   42.00   80.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       74.0000   76.0000   18.5036 38

#__ type_ start__ end____ width___ exp.time_
 35 omega   75.00  106.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      107.1410   77.0000 -180.0000 31

#__ type_ start__ end____ width___ exp.time_
 36 omega   75.00  163.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      107.1410   77.0000  150.0000 88

#__ type_ start__ end____ width___ exp.time_
 37 omega   75.00  170.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      107.1410   77.0000   90.0000 95

#__ type_ start__ end____ width___ exp.time_
 38 omega   58.00   95.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      107.1410  -45.0000  -90.0000 37

#__ type_ start__ end____ width___ exp.time_
 39 omega   75.00  101.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      107.1410   77.0000  -30.0000 26

#__ type_ start__ end____ width___ exp.time_
 40 omega   72.00   98.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      107.1410 -125.0000   90.0000 26

#__ type_ start__ end____ width___ exp.time_
 41 omega   76.00  143.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      107.1410   77.0000    0.0000 67

#__ type_ start__ end____ width___ exp.time_
 42 omega   34.00   67.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      107.1410 -125.0000   90.0000 33

#__ type_ start__ end____ width___ exp.time_
 43 omega   75.00  178.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      107.1410   77.0000  -60.0000 103

#__ type_ start__ end____ width___ exp.time_
 44 omega   79.00  122.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      107.1410   61.0000 -120.0000 43

#__ type_ start__ end____ width___ exp.time_
 45 omega   31.00  111.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      107.1410 -101.0000  -52.0000 80

#__ type_ start__ end____ width___ exp.time_
 46 omega   79.00  104.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      107.1410   61.0000   60.0000 25

#__ type_ start__ end____ width___ exp.time_
 47 omega   78.00  117.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      107.1410   61.0000    0.0000 39

#__ type_ start__ end____ width___ exp.time_
 48 omega   75.00  104.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      107.1410   77.0000 -150.0000 29

#__ type_ start__ end____ width___ exp.time_
 49 omega   78.00  156.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      107.1410   61.0000 -150.0000 78

#__ type_ start__ end____ width___ exp.time_
 50 omega   42.00  121.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      107.1410 -125.0000 -180.0000 79

#__ type_ start__ end____ width___ exp.time_
 51 omega   75.00  146.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      107.1410   77.0000  -90.0000 71

#__ type_ start__ end____ width___ exp.time_
 52 omega  148.00  175.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      107.1410   77.0000 -120.0000 27

#__ type_ start__ end____ width___ exp.time_
 53 omega   75.00  152.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      107.1410   77.0000   30.0000 77

#__ type_ start__ end____ width___ exp.time_
 54 omega   78.00  104.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      107.1410   61.0000 -180.0000 26

#__ type_ start__ end____ width___ exp.time_
 55 omega   79.00  124.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      107.1410   61.0000  150.0000 45

#__ type_ start__ end____ width___ exp.time_
 56 omega  122.00  149.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      107.1410   77.0000  120.0000 27

#__ type_ start__ end____ width___ exp.time_
 57 omega   75.00  130.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      107.1410   77.0000 -120.0000 55

#__ type_ start__ end____ width___ exp.time_
 58 omega   75.00  101.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      107.1410   77.0000  120.0000 26

#__ type_ start__ end____ width___ exp.time_
 59 omega   75.00  143.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      107.1410   77.0000   60.0000 68

#__ type_ start__ end____ width___ exp.time_
 60 omega  118.00  143.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      107.1410   77.0000  -30.0000 25

#__ type_ start__ end____ width___ exp.time_
 61 omega   84.00  109.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      107.1410  -95.0000 -150.0000 25

#__ type_ start__ end____ width___ exp.time_
 62 omega   84.00  109.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      107.1410  -95.0000  120.0000 25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0598143000
_diffrn_orient_matrix_UB_12      -0.0179338000
_diffrn_orient_matrix_UB_13      -0.0507045000
_diffrn_orient_matrix_UB_21      0.0662621000
_diffrn_orient_matrix_UB_22      0.1615083000
_diffrn_orient_matrix_UB_23      -0.0009226000
_diffrn_orient_matrix_UB_31      0.1983507000
_diffrn_orient_matrix_UB_32      -0.0485259000
_diffrn_orient_matrix_UB_33      0.0156195000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                3241
_reflns_number_total             3334
_reflns_odcompleteness_completeness 99.90
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_refine_diff_density_max         0.143
_refine_diff_density_min         -0.246
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.005(14)
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         3334
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0345
_refine_ls_R_factor_gt           0.0337
_refine_ls_restrained_S_all      1.030
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0611P)²+0.2179P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0923
_refine_ls_wR_factor_ref         0.0935
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_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:
 C1(H1A,H1B), C4(H4A,H4B)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C8(H8), C10(H10), C11(H11), C13(H13), C14(H14), C16(H16),
 C17(H17), C19(H19), C20(H20)
2.c Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
C1 C 0.2633(3) 0.7806(2) 0.32233(7) 0.0542(4) Uani 1 d . . .
H1A H 0.1457 0.8072 0.3074 0.065 Uiso 1 calc . . R
H1B H 0.2505 0.6841 0.3363 0.065 Uiso 1 calc . . R
C2 C 0.4258(3) 0.78581(19) 0.28948(6) 0.0454(4) Uani 1 d . . .
C3 C 0.5780(3) 0.86058(18) 0.30854(6) 0.0431(4) Uani 1 d . . .
C4 C 0.5299(3) 0.9084(2) 0.35688(6) 0.0515(4) Uani 1 d . . .
H4A H 0.5878 0.8447 0.3797 0.062 Uiso 1 calc . . R
H4B H 0.5676 1.0094 0.3626 0.062 Uiso 1 calc . . R
C5 C 0.4372(3) 0.7295(2) 0.24529(7) 0.0546(5) Uani 1 d . . .
H5 H 0.3358 0.6789 0.2325 0.066 Uiso 1 calc . . R
C6 C 0.6008(3) 0.7496(2) 0.22049(7) 0.0515(4) Uani 1 d . . .
H6 H 0.6085 0.7114 0.1908 0.062 Uiso 1 calc . . R
C7 C 0.7561(3) 0.82582(18) 0.23860(6) 0.0421(4) Uani 1 d . . .
C8 C 0.7433(2) 0.88048(18) 0.28394(6) 0.0426(4) Uani 1 d . . .
H8 H 0.8451 0.9294 0.2972 0.051 Uiso 1 calc . . R
C9 C 0.9258(3) 0.84983(18) 0.20977(6) 0.0434(4) Uani 1 d . . .
C10 C 0.9721(3) 0.7522(2) 0.17423(7) 0.0497(4) Uani 1 d . . .
H10 H 0.8986 0.6684 0.1699 0.060 Uiso 1 calc . . R
C11 C 1.1244(3) 0.7768(2) 0.14531(7) 0.0557(5) Uani 1 d . . .
H11 H 1.1533 0.7102 0.1220 0.067 Uiso 1 calc . . R
C12 C 1.2322(3) 0.9011(2) 0.15148(7) 0.0565(5) Uani 1 d . . .
C13 C 1.1929(3) 0.9979(2) 0.18686(8) 0.0600(5) Uani 1 d . . .
H13 H 1.2691 1.0801 0.1914 0.072 Uiso 1 calc . . R
C14 C 1.0410(3) 0.9728(2) 0.21541(7) 0.0524(4) Uani 1 d . . .
H14 H 1.0148 1.0393 0.2389 0.063 Uiso 1 calc . . R
C15 C 0.2090(3) 0.7445(2) 0.43384(6) 0.0490(4) Uani 1 d . . .
C16 C 0.0730(3) 0.6377(3) 0.42745(8) 0.0646(6) Uani 1 d . . .
H16 H -0.0252 0.6535 0.4068 0.078 Uiso 1 calc . . R
C17 C 0.0830(4) 0.5077(3) 0.45169(8) 0.0680(6) Uani 1 d . . .
H17 H -0.0093 0.4363 0.4472 0.082 Uiso 1 calc . . R
C18 C 0.2274(4) 0.4811(2) 0.48266(7) 0.0605(5) Uani 1 d . . .
C19 C 0.3642(4) 0.5869(3) 0.48777(8) 0.0718(6) Uani 1 d . . .
H19 H 0.4646 0.5697 0.5077 0.086 Uiso 1 calc . . R
C20 C 0.3561(4) 0.7192(3) 0.46381(8) 0.0675(6) Uani 1 d . . .
H20 H 0.4492 0.7901 0.4680 0.081 Uiso 1 calc . . R
C21 C 0.2328(6) 0.3402(3) 0.51024(10) 0.0910(9) Uani 1 d . . .
H21A H 0.1204 0.3327 0.5286 0.137 Uiso 1 calc . . GR
H21B H 0.3415 0.3406 0.5300 0.137 Uiso 1 calc . . GR
H21C H 0.2399 0.2577 0.4897 0.137 Uiso 1 calc . . GR
Cl1 Cl 1.42119(11) 0.93557(9) 0.11493(2) 0.0897(2) Uani 1 d . . .
N1 N 0.3214(2) 0.89235(18) 0.35640(5) 0.0504(4) Uani 1 d . . .
O1 O 0.0051(2) 0.92894(19) 0.38830(6) 0.0708(5) Uani 1 d . . .
O2 O 0.2854(3) 1.02390(17) 0.42954(6) 0.0753(5) Uani 1 d . . .
S1 S 0.19644(7) 0.91133(5) 0.403115(17) 0.05525(15) Uani 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 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C1 C2 1.495(3) . ?
C1 N1 1.476(3) . ?
C2 C3 1.389(3) . ?
C2 C5 1.383(3) . ?
C3 C4 1.508(2) . ?
C3 C8 1.383(3) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 N1 1.484(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.376(3) . ?
C6 H6 0.9300 . ?
C6 C7 1.402(3) . ?
C7 C8 1.410(2) . ?
C7 C9 1.481(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.400(3) . ?
C9 C14 1.393(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.385(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.375(3) . ?
C12 C13 1.381(3) . ?
C12 Cl1 1.737(2) . ?
C13 H13 0.9300 . ?
C13 C14 1.377(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.379(3) . ?
C15 C20 1.376(3) . ?
C15 S1 1.7613(19) . ?
C16 H16 0.9300 . ?
C16 C17 1.377(3) . ?
C17 H17 0.9300 . ?
C17 C18 1.383(3) . ?
C18 C19 1.373(3) . ?
C18 C21 1.510(3) . ?
C19 H19 0.9300 . ?
C19 C20 1.390(3) . ?
C20 H20 0.9300 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
N1 S1 1.6287(16) . ?
O1 S1 1.4309(17) . ?
O2 S1 1.4251(17) . ?

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
H1A C1 H1B 109.4 . . ?
C2 C1 H1A 111.6 . . ?
C2 C1 H1B 111.6 . . ?
N1 C1 H1A 111.6 . . ?
N1 C1 H1B 111.6 . . ?
N1 C1 C2 101.03(15) . . ?
C3 C2 C1 111.01(16) . . ?
C5 C2 C1 128.68(17) . . ?
C5 C2 C3 120.31(18) . . ?
C2 C3 C4 109.66(16) . . ?
C8 C3 C2 120.99(16) . . ?
C8 C3 C4 129.35(16) . . ?
C3 C4 H4A 111.6 . . ?
C3 C4 H4B 111.6 . . ?
H4A C4 H4B 109.4 . . ?
N1 C4 C3 100.81(15) . . ?
N1 C4 H4A 111.6 . . ?
N1 C4 H4B 111.6 . . ?
C2 C5 H5 120.5 . . ?
C6 C5 C2 119.07(18) . . ?
C6 C5 H5 120.5 . . ?
C5 C6 H6 119.0 . . ?
C5 C6 C7 121.97(17) . . ?
C7 C6 H6 119.0 . . ?
C6 C7 C8 118.28(17) . . ?
C6 C7 C9 119.84(16) . . ?
C8 C7 C9 121.87(16) . . ?
C3 C8 C7 119.36(16) . . ?
C3 C8 H8 120.3 . . ?
C7 C8 H8 120.3 . . ?
C10 C9 C7 120.91(16) . . ?
C14 C9 C7 121.81(16) . . ?
C14 C9 C10 117.23(18) . . ?
C9 C10 H10 119.1 . . ?
C11 C10 C9 121.81(18) . . ?
C11 C10 H10 119.1 . . ?
C10 C11 H11 120.5 . . ?
C12 C11 C10 119.07(18) . . ?
C12 C11 H11 120.5 . . ?
C11 C12 C13 120.58(19) . . ?
C11 C12 Cl1 119.76(17) . . ?
C13 C12 Cl1 119.65(17) . . ?
C12 C13 H13 120.0 . . ?
C14 C13 C12 120.0(2) . . ?
C14 C13 H13 120.0 . . ?
C9 C14 H14 119.3 . . ?
C13 C14 C9 121.31(19) . . ?
C13 C14 H14 119.3 . . ?
C16 C15 S1 120.12(15) . . ?
C20 C15 C16 119.76(19) . . ?
C20 C15 S1 120.11(17) . . ?
C15 C16 H16 120.0 . . ?
C17 C16 C15 119.9(2) . . ?
C17 C16 H16 120.0 . . ?
C16 C17 H17 119.3 . . ?
C16 C17 C18 121.3(2) . . ?
C18 C17 H17 119.3 . . ?
C17 C18 C21 120.7(2) . . ?
C19 C18 C17 118.03(19) . . ?
C19 C18 C21 121.2(2) . . ?
C18 C19 H19 119.3 . . ?
C18 C19 C20 121.5(2) . . ?
C20 C19 H19 119.3 . . ?
C15 C20 C19 119.5(2) . . ?
C15 C20 H20 120.3 . . ?
C19 C20 H20 120.3 . . ?
C18 C21 H21A 109.5 . . ?
C18 C21 H21B 109.5 . . ?
C18 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C1 N1 C4 110.55(15) . . ?
C1 N1 S1 118.67(13) . . ?
C4 N1 S1 121.49(13) . . ?
N1 S1 C15 107.66(9) . . ?
O1 S1 C15 107.23(10) . . ?
O1 S1 N1 106.02(9) . . ?
O2 S1 C15 108.82(10) . . ?
O2 S1 N1 106.52(10) . . ?
O2 S1 O1 120.02(12) . . ?

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
C1 C2 C3 C4 1.5(2) . . . . ?
C1 C2 C3 C8 -179.19(16) . . . . ?
C1 C2 C5 C6 178.7(2) . . . . ?
C1 N1 S1 C15 62.65(17) . . . . ?
C1 N1 S1 O1 -51.87(17) . . . . ?
C1 N1 S1 O2 179.23(15) . . . . ?
C2 C1 N1 C4 -25.4(2) . . . . ?
C2 C1 N1 S1 -172.66(13) . . . . ?
C2 C3 C4 N1 -16.5(2) . . . . ?
C2 C3 C8 C7 1.0(3) . . . . ?
C2 C5 C6 C7 -0.2(3) . . . . ?
C3 C2 C5 C6 -0.4(3) . . . . ?
C3 C4 N1 C1 26.3(2) . . . . ?
C3 C4 N1 S1 172.41(12) . . . . ?
C4 C3 C8 C7 -179.88(17) . . . . ?
C4 N1 S1 C15 -80.87(18) . . . . ?
C4 N1 S1 O1 164.62(16) . . . . ?
C4 N1 S1 O2 35.71(19) . . . . ?
C5 C2 C3 C4 -179.26(18) . . . . ?
C5 C2 C3 C8 0.1(3) . . . . ?
C5 C6 C7 C8 1.2(3) . . . . ?
C5 C6 C7 C9 -177.41(18) . . . . ?
C6 C7 C8 C3 -1.6(2) . . . . ?
C6 C7 C9 C10 -27.3(3) . . . . ?
C6 C7 C9 C14 149.86(19) . . . . ?
C7 C9 C10 C11 176.50(18) . . . . ?
C7 C9 C14 C13 -176.62(19) . . . . ?
C8 C3 C4 N1 164.30(17) . . . . ?
C8 C7 C9 C10 154.07(17) . . . . ?
C8 C7 C9 C14 -28.7(3) . . . . ?
C9 C7 C8 C3 177.04(15) . . . . ?
C9 C10 C11 C12 -0.5(3) . . . . ?
C10 C9 C14 C13 0.7(3) . . . . ?
C10 C11 C12 C13 1.9(3) . . . . ?
C10 C11 C12 Cl1 -178.87(16) . . . . ?
C11 C12 C13 C14 -2.1(3) . . . . ?
C12 C13 C14 C9 0.7(3) . . . . ?
C14 C9 C10 C11 -0.8(3) . . . . ?
C15 C16 C17 C18 0.0(4) . . . . ?
C16 C15 C20 C19 -0.9(3) . . . . ?
C16 C15 S1 N1 -92.81(19) . . . . ?
C16 C15 S1 O1 20.9(2) . . . . ?
C16 C15 S1 O2 152.12(18) . . . . ?
C16 C17 C18 C19 -1.7(4) . . . . ?
C16 C17 C18 C21 177.9(3) . . . . ?
C17 C18 C19 C20 2.0(4) . . . . ?
C18 C19 C20 C15 -0.8(4) . . . . ?
C20 C15 C16 C17 1.2(4) . . . . ?
C20 C15 S1 N1 86.21(18) . . . . ?
C20 C15 S1 O1 -160.08(18) . . . . ?
C20 C15 S1 O2 -28.9(2) . . . . ?
C21 C18 C19 C20 -177.5(3) . . . . ?
Cl1 C12 C13 C14 178.71(17) . . . . ?
N1 C1 C2 C3 14.2(2) . . . . ?
N1 C1 C2 C5 -164.91(19) . . . . ?
S1 C15 C16 C17 -179.72(19) . . . . ?
S1 C15 C20 C19 -179.90(19) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
