# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_171222_syy_11_22_7
_database_code_depnum_ccdc_archive 'CCDC 1828914'
_audit_update_record             
;
2018-03-12 deposited with the CCDC.
2018-11-12 downloaded from the CCDC.
;
_audit_creation_date             2017-12-22
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H16 N2 O6 S'
_chemical_formula_sum            'C19 H16 N2 O6 S'
_chemical_formula_weight         400.40
_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 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   9.7218(8)
_cell_length_b                   7.7915(6)
_cell_length_c                   24.097(2)
_cell_angle_alpha                90
_cell_angle_beta                 99.734(8)
_cell_angle_gamma                90
_cell_volume                     1799.0(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2218
_cell_measurement_temperature    155.9
_cell_measurement_theta_max      29.4696
_cell_measurement_theta_min      3.0419
_shelx_estimated_absorpt_T_max   0.941
_shelx_estimated_absorpt_T_min   0.913
_exptl_absorpt_coefficient_mu    0.221
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84470
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.478
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             832
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.28
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0415
_diffrn_reflns_av_unetI/netI     0.0490
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            7376
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.350
_diffrn_reflns_theta_min         3.431
_diffrn_ambient_temperature      155.9
_diffrn_detector_area_resol_mean 10.3592
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -85.00    1.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.4683  -38.0000  150.0000 86

#__ type_ start__ end____ width___ exp.time_
  2 omega  -88.00   17.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.4683  -77.0000   60.0000 105
;
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0454323000
_diffrn_orient_matrix_UB_12      0.0084607000
_diffrn_orient_matrix_UB_13      -0.0262257000
_diffrn_orient_matrix_UB_21      -0.0034587000
_diffrn_orient_matrix_UB_22      -0.0905404000
_diffrn_orient_matrix_UB_23      -0.0026403000
_diffrn_orient_matrix_UB_31      -0.0583080000
_diffrn_orient_matrix_UB_32      -0.0012270000
_diffrn_orient_matrix_UB_33      0.0141374000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2495
_reflns_number_total             3285
_reflns_odcompleteness_completeness 99.52
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.387
_refine_diff_density_min         -0.456
_refine_diff_density_rms         0.060
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         3285
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0666
_refine_ls_R_factor_gt           0.0484
_refine_ls_restrained_S_all      1.041
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0654P)²+0.4966P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1183
_refine_ls_wR_factor_ref         0.1359
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C8(H8), C9(H9), C10(H10), C11(H11), C12(H12), C15(H15),
 C16(H16), C18(H18), C19(H19)
2.c Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.14429(6) 0.67871(8) 0.23064(3) 0.0276(2) Uani 1 1 d . . . . .
O1 O 0.19584(19) 0.7482(2) 0.01195(8) 0.0401(5) Uani 1 1 d . . . . .
O2 O 0.10938(17) 0.6952(2) 0.08979(7) 0.0293(4) Uani 1 1 d . . . . .
O3 O 0.21855(17) 0.5203(2) 0.23703(8) 0.0330(4) Uani 1 1 d . . . . .
O4 O 0.07327(17) 0.7399(2) 0.27404(7) 0.0345(5) Uani 1 1 d . . . . .
O5 O 0.4803(2) 1.3782(3) 0.17601(10) 0.0548(6) Uani 1 1 d . . . . .
O6 O 0.6094(2) 1.1917(3) 0.14441(12) 0.0670(7) Uani 1 1 d . . . . .
N1 N 0.02291(19) 0.6623(3) 0.17310(9) 0.0277(5) Uani 1 1 d . . . . .
N2 N 0.5103(2) 1.2307(3) 0.16636(10) 0.0395(6) Uani 1 1 d . . . . .
C1 C 0.1607(2) 0.6392(3) 0.04174(10) 0.0298(6) Uani 1 1 d . . . . .
C2 C 0.1645(2) 0.4561(3) 0.03451(11) 0.0305(6) Uani 1 1 d . . . . .
H2 H 0.200218 0.411407 0.003131 0.037 Uiso 1 1 calc R . . . .
C3 C 0.1190(2) 0.3448(3) 0.07077(10) 0.0288(6) Uani 1 1 d . . . . .
C4 C 0.0663(2) 0.4118(3) 0.11835(10) 0.0293(6) Uani 1 1 d . . . . .
H4 H 0.032269 0.336756 0.143985 0.035 Uiso 1 1 calc R . . . .
C5 C 0.0656(2) 0.5808(3) 0.12612(10) 0.0272(6) Uani 1 1 d . . . . .
C6 C -0.0706(2) 0.8140(3) 0.16103(11) 0.0310(6) Uani 1 1 d . . . . .
H6A H -0.017608 0.909788 0.147757 0.037 Uiso 1 1 calc R . . . .
H6B H -0.101406 0.851138 0.196264 0.037 Uiso 1 1 calc R . . . .
C7 C -0.1967(2) 0.7768(3) 0.11740(11) 0.0297(6) Uani 1 1 d . . . . .
C8 C -0.2412(3) 0.9027(4) 0.07719(12) 0.0369(7) Uani 1 1 d . . . . .
H8 H -0.188972 1.005635 0.076775 0.044 Uiso 1 1 calc R . . . .
C9 C -0.3607(3) 0.8786(4) 0.03802(13) 0.0439(7) Uani 1 1 d . . . . .
H9 H -0.389454 0.964677 0.010575 0.053 Uiso 1 1 calc R . . . .
C10 C -0.4388(3) 0.7310(4) 0.03828(13) 0.0440(7) Uani 1 1 d . . . . .
H10 H -0.521796 0.715966 0.011608 0.053 Uiso 1 1 calc R . . . .
C11 C -0.3951(3) 0.6048(4) 0.07780(12) 0.0404(7) Uani 1 1 d . . . . .
H11 H -0.448090 0.502457 0.078118 0.049 Uiso 1 1 calc R . . . .
C12 C -0.2746(3) 0.6271(4) 0.11682(11) 0.0346(6) Uani 1 1 d . . . . .
H12 H -0.244772 0.539164 0.143469 0.042 Uiso 1 1 calc R . . . .
C13 C 0.1208(3) 0.1542(3) 0.06228(12) 0.0388(7) Uani 1 1 d . . . . .
H13A H 0.024725 0.111267 0.054054 0.058 Uiso 1 1 calc GR . . . .
H13B H 0.169927 0.099175 0.096541 0.058 Uiso 1 1 calc GR . . . .
H13C H 0.168779 0.127576 0.030691 0.058 Uiso 1 1 calc GR . . . .
C14 C 0.2599(2) 0.8401(3) 0.21479(10) 0.0264(6) Uani 1 1 d . . . . .
C15 C 0.3693(3) 0.7957(3) 0.18740(11) 0.0314(6) Uani 1 1 d . . . . .
H15 H 0.386013 0.678963 0.179342 0.038 Uiso 1 1 calc R . . . .
C16 C 0.4536(2) 0.9239(3) 0.17201(11) 0.0328(6) Uani 1 1 d . . . . .
H16 H 0.529576 0.897411 0.153356 0.039 Uiso 1 1 calc R . . . .
C17 C 0.4245(2) 1.0914(3) 0.18444(11) 0.0300(6) Uani 1 1 d . . . . .
C18 C 0.3174(2) 1.1370(3) 0.21225(11) 0.0317(6) Uani 1 1 d . . . . .
H18 H 0.301818 1.253768 0.220669 0.038 Uiso 1 1 calc R . . . .
C19 C 0.2333(2) 1.0088(3) 0.22759(11) 0.0295(6) Uani 1 1 d . . . . .
H19 H 0.158146 1.035897 0.246660 0.035 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O3 1.4249(18) . ?
S1 O4 1.4290(17) . ?
S1 N1 1.667(2) . ?
S1 C14 1.771(2) . ?
O1 C1 1.199(3) . ?
O2 C1 1.406(3) . ?
O2 C5 1.367(3) . ?
O5 N2 1.218(3) . ?
O6 N2 1.214(3) . ?
N1 C5 1.420(3) . ?
N1 C6 1.490(3) . ?
N2 C17 1.478(3) . ?
C1 C2 1.438(4) . ?
C2 H2 0.9500 . ?
C2 C3 1.357(3) . ?
C3 C4 1.431(3) . ?
C3 C13 1.500(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.330(3) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C7 1.502(4) . ?
C7 C8 1.395(4) . ?
C7 C12 1.389(4) . ?
C8 H8 0.9500 . ?
C8 C9 1.380(4) . ?
C9 H9 0.9500 . ?
C9 C10 1.379(4) . ?
C10 H10 0.9500 . ?
C10 C11 1.384(4) . ?
C11 H11 0.9500 . ?
C11 C12 1.384(4) . ?
C12 H12 0.9500 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 C15 1.387(3) . ?
C14 C19 1.384(3) . ?
C15 H15 0.9500 . ?
C15 C16 1.382(3) . ?
C16 H16 0.9500 . ?
C16 C17 1.378(3) . ?
C17 C18 1.376(3) . ?
C18 H18 0.9500 . ?
C18 C19 1.381(4) . ?
C19 H19 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O3 S1 O4 120.56(11) . . ?
O3 S1 N1 107.34(11) . . ?
O3 S1 C14 108.05(11) . . ?
O4 S1 N1 105.83(10) . . ?
O4 S1 C14 108.90(11) . . ?
N1 S1 C14 105.13(11) . . ?
C5 O2 C1 121.19(19) . . ?
C5 N1 S1 115.87(15) . . ?
C5 N1 C6 116.8(2) . . ?
C6 N1 S1 115.10(16) . . ?
O5 N2 C17 118.1(2) . . ?
O6 N2 O5 123.6(2) . . ?
O6 N2 C17 118.3(2) . . ?
O1 C1 O2 116.8(2) . . ?
O1 C1 C2 127.9(2) . . ?
O2 C1 C2 115.3(2) . . ?
C1 C2 H2 118.7 . . ?
C3 C2 C1 122.5(2) . . ?
C3 C2 H2 118.7 . . ?
C2 C3 C4 118.8(2) . . ?
C2 C3 C13 122.2(2) . . ?
C4 C3 C13 119.0(2) . . ?
C3 C4 H4 120.5 . . ?
C5 C4 C3 119.0(2) . . ?
C5 C4 H4 120.5 . . ?
O2 C5 N1 112.6(2) . . ?
C4 C5 O2 123.1(2) . . ?
C4 C5 N1 124.3(2) . . ?
N1 C6 H6A 109.1 . . ?
N1 C6 H6B 109.1 . . ?
N1 C6 C7 112.5(2) . . ?
H6A C6 H6B 107.8 . . ?
C7 C6 H6A 109.1 . . ?
C7 C6 H6B 109.1 . . ?
C8 C7 C6 118.1(2) . . ?
C12 C7 C6 123.2(2) . . ?
C12 C7 C8 118.6(2) . . ?
C7 C8 H8 119.8 . . ?
C9 C8 C7 120.4(3) . . ?
C9 C8 H8 119.8 . . ?
C8 C9 H9 119.6 . . ?
C10 C9 C8 120.7(3) . . ?
C10 C9 H9 119.6 . . ?
C9 C10 H10 120.3 . . ?
C9 C10 C11 119.4(3) . . ?
C11 C10 H10 120.3 . . ?
C10 C11 H11 119.9 . . ?
C12 C11 C10 120.3(3) . . ?
C12 C11 H11 119.9 . . ?
C7 C12 H12 119.7 . . ?
C11 C12 C7 120.6(3) . . ?
C11 C12 H12 119.7 . . ?
C3 C13 H13A 109.5 . . ?
C3 C13 H13B 109.5 . . ?
C3 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C15 C14 S1 119.44(19) . . ?
C19 C14 S1 118.45(18) . . ?
C19 C14 C15 122.0(2) . . ?
C14 C15 H15 120.5 . . ?
C16 C15 C14 119.0(2) . . ?
C16 C15 H15 120.5 . . ?
C15 C16 H16 120.9 . . ?
C17 C16 C15 118.2(2) . . ?
C17 C16 H16 120.9 . . ?
C16 C17 N2 118.9(2) . . ?
C18 C17 N2 117.7(2) . . ?
C18 C17 C16 123.4(2) . . ?
C17 C18 H18 120.8 . . ?
C17 C18 C19 118.3(2) . . ?
C19 C18 H18 120.8 . . ?
C14 C19 H19 120.5 . . ?
C18 C19 C14 119.0(2) . . ?
C18 C19 H19 120.5 . . ?

_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_170104_syy_11_25_2
_database_code_depnum_ccdc_archive 'CCDC 1828915'
_audit_update_record             
;
2018-03-12 deposited with the CCDC.
2018-11-12 downloaded from the CCDC.
;
_audit_creation_date             2018-01-04
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H19 N O4 S'
_chemical_formula_sum            'C20 H19 N O4 S'
_chemical_formula_weight         369.42
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N O S'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   6.4452(7)
_cell_length_b                   11.7323(11)
_cell_length_c                   12.5163(12)
_cell_angle_alpha                105.865(8)
_cell_angle_beta                 90.612(8)
_cell_angle_gamma                93.872(8)
_cell_volume                     907.90(15)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1480
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.1736
_cell_measurement_theta_min      3.3656
_shelx_estimated_absorpt_T_max   0.960
_shelx_estimated_absorpt_T_min   0.907
_exptl_absorpt_coefficient_mu    0.203
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83932
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.351
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             388
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0327
_diffrn_reflns_av_unetI/netI     0.0556
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            5868
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.346
_diffrn_reflns_theta_min         3.372
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean 10.3592
_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  -56.00   33.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -       11.7808  -38.0000  120.0000 89

#__ type_ start__ end____ width___ exp.time_
  2 omega  -19.00   81.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -       11.7808   77.0000   30.0000 100

#__ type_ start__ end____ width___ exp.time_
  3 omega  -15.00   82.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -       11.7808   38.0000  -60.0000 97
;
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0233447000
_diffrn_orient_matrix_UB_12      -0.0263082000
_diffrn_orient_matrix_UB_13      0.0435892000
_diffrn_orient_matrix_UB_21      0.0305297000
_diffrn_orient_matrix_UB_22      0.0546412000
_diffrn_orient_matrix_UB_23      0.0396745000
_diffrn_orient_matrix_UB_31      -0.1034452000
_diffrn_orient_matrix_UB_32      0.0171391000
_diffrn_orient_matrix_UB_33      -0.0000370000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2365
_reflns_number_total             3319
_reflns_odcompleteness_completeness 99.52
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.171
_refine_diff_density_min         -0.313
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     238
_refine_ls_number_reflns         3319
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0762
_refine_ls_R_factor_gt           0.0508
_refine_ls_restrained_S_all      1.031
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0597P)²+0.0974P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1158
_refine_ls_wR_factor_ref         0.1339
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C4(H4), C5(H5), C12(H12), C15(H15), C16(H16), C17(H17),
 C18(H18), C19(H19)
2.b Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C8(H8A,H8B,H8C), C20(H20A,H20B,H20C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.22720(10) 0.27312(6) 0.83116(5) 0.0492(2) Uani 1 1 d . . . . .
O1 O 0.2504(3) 0.30327(18) 0.94931(15) 0.0714(6) Uani 1 1 d . . . . .
O2 O 0.0262(3) 0.25868(16) 0.77839(16) 0.0598(5) Uani 1 1 d . . . . .
O3 O 0.2979(2) 0.13298(13) 0.60095(13) 0.0380(4) Uani 1 1 d . . . . .
O4 O 0.2760(3) 0.14175(16) 0.42711(14) 0.0495(5) Uani 1 1 d . . . . .
N1 N 0.3300(3) 0.14409(17) 0.78669(16) 0.0419(5) Uani 1 1 d . . . . .
C1 C 0.5737(4) 0.4215(2) 0.8401(2) 0.0556(7) Uani 1 1 d . . . . .
H1 H 0.609821 0.402689 0.905040 0.067 Uiso 1 1 calc R . . . .
C2 C 0.7074(4) 0.4945(2) 0.7979(2) 0.0562(7) Uani 1 1 d . . . . .
H2 H 0.834546 0.523477 0.834322 0.067 Uiso 1 1 calc R . . . .
C3 C 0.6555(4) 0.5252(2) 0.7024(2) 0.0498(7) Uani 1 1 d . . . . .
C4 C 0.4632(4) 0.4837(2) 0.6522(2) 0.0536(7) Uani 1 1 d . . . . .
H4 H 0.422970 0.507085 0.590212 0.064 Uiso 1 1 calc R . . . .
C5 C 0.3287(4) 0.4085(2) 0.6912(2) 0.0502(7) Uani 1 1 d . . . . .
H5 H 0.201526 0.379744 0.654697 0.060 Uiso 1 1 calc R . . . .
C6 C 0.3860(4) 0.3767(2) 0.7852(2) 0.0436(6) Uani 1 1 d . . . . .
C7 C 0.8068(5) 0.5990(3) 0.6533(3) 0.0730(9) Uani 1 1 d . . . . .
H7A H 0.888899 0.547611 0.599815 0.109 Uiso 1 1 calc GR . . . .
H7B H 0.896431 0.649562 0.711272 0.109 Uiso 1 1 calc GR . . . .
H7C H 0.731474 0.646851 0.617487 0.109 Uiso 1 1 calc GR . . . .
C8 C 0.5171(5) 0.1234(3) 0.8449(2) 0.0657(8) Uani 1 1 d . . . . .
H8A H 0.633455 0.171863 0.830412 0.099 Uiso 1 1 calc GR . . . .
H8B H 0.545039 0.041149 0.819022 0.099 Uiso 1 1 calc GR . . . .
H8C H 0.494807 0.143509 0.923402 0.099 Uiso 1 1 calc GR . . . .
C9 C 0.2836(3) 0.0715(2) 0.67864(19) 0.0356(5) Uani 1 1 d . . . . .
C10 C 0.2429(3) -0.0472(2) 0.65296(19) 0.0346(5) Uani 1 1 d . . . . .
C11 C 0.2253(3) -0.1104(2) 0.53608(19) 0.0349(5) Uani 1 1 d . . . . .
C12 C 0.2349(3) -0.0487(2) 0.45954(19) 0.0374(6) Uani 1 1 d . . . . .
H12 H 0.219461 -0.090475 0.384843 0.045 Uiso 1 1 calc R . . . .
C13 C 0.2676(3) 0.0773(2) 0.4878(2) 0.0370(6) Uani 1 1 d . . . . .
C14 C 0.2119(4) -0.1082(2) 0.74213(19) 0.0377(6) Uani 1 1 d . . . . .
C15 C 0.0392(4) -0.0879(2) 0.8081(2) 0.0467(6) Uani 1 1 d . . . . .
H15 H -0.056488 -0.036484 0.796078 0.056 Uiso 1 1 calc R . . . .
C16 C 0.0080(4) -0.1434(3) 0.8912(2) 0.0577(7) Uani 1 1 d . . . . .
H16 H -0.108379 -0.129101 0.934880 0.069 Uiso 1 1 calc R . . . .
C17 C 0.1478(5) -0.2194(3) 0.9099(2) 0.0578(8) Uani 1 1 d . . . . .
H17 H 0.125427 -0.257474 0.965314 0.069 Uiso 1 1 calc R . . . .
C18 C 0.3205(5) -0.2391(3) 0.8466(2) 0.0585(8) Uani 1 1 d . . . . .
H18 H 0.417047 -0.289239 0.860268 0.070 Uiso 1 1 calc R . . . .
C19 C 0.3522(4) -0.1848(2) 0.7623(2) 0.0490(7) Uani 1 1 d . . . . .
H19 H 0.468664 -0.199849 0.718772 0.059 Uiso 1 1 calc R . . . .
C20 C 0.1945(4) -0.2434(2) 0.5004(2) 0.0501(7) Uani 1 1 d . . . . .
H20A H 0.315373 -0.276546 0.521656 0.075 Uiso 1 1 calc GR . . . .
H20B H 0.173537 -0.270364 0.421152 0.075 Uiso 1 1 calc GR . . . .
H20C H 0.074892 -0.268560 0.535496 0.075 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O1 1.427(2) . ?
S1 O2 1.426(2) . ?
S1 N1 1.650(2) . ?
S1 C6 1.756(3) . ?
O3 C9 1.360(2) . ?
O3 C13 1.393(3) . ?
O4 C13 1.209(3) . ?
N1 C8 1.470(3) . ?
N1 C9 1.404(3) . ?
C1 H1 0.9300 . ?
C1 C2 1.383(4) . ?
C1 C6 1.382(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.382(4) . ?
C3 C4 1.380(4) . ?
C3 C7 1.506(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.382(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.382(3) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 C10 1.348(3) . ?
C10 C11 1.447(3) . ?
C10 C14 1.489(3) . ?
C11 C12 1.349(3) . ?
C11 C20 1.500(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.424(3) . ?
C14 C15 1.387(3) . ?
C14 C19 1.384(3) . ?
C15 H15 0.9300 . ?
C15 C16 1.380(3) . ?
C16 H16 0.9300 . ?
C16 C17 1.371(4) . ?
C17 H17 0.9300 . ?
C17 C18 1.369(4) . ?
C18 H18 0.9300 . ?
C18 C19 1.384(3) . ?
C19 H19 0.9300 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 S1 N1 104.86(12) . . ?
O1 S1 C6 107.57(12) . . ?
O2 S1 O1 120.85(12) . . ?
O2 S1 N1 106.31(11) . . ?
O2 S1 C6 109.64(12) . . ?
N1 S1 C6 106.73(10) . . ?
C9 O3 C13 122.09(18) . . ?
C8 N1 S1 118.62(18) . . ?
C9 N1 S1 120.33(15) . . ?
C9 N1 C8 118.19(19) . . ?
C2 C1 H1 120.2 . . ?
C6 C1 H1 120.2 . . ?
C6 C1 C2 119.6(3) . . ?
C1 C2 H2 119.4 . . ?
C3 C2 C1 121.2(3) . . ?
C3 C2 H2 119.4 . . ?
C2 C3 C7 120.9(3) . . ?
C4 C3 C2 118.0(2) . . ?
C4 C3 C7 121.1(3) . . ?
C3 C4 H4 119.0 . . ?
C3 C4 C5 121.9(3) . . ?
C5 C4 H4 119.0 . . ?
C4 C5 H5 120.5 . . ?
C6 C5 C4 119.0(3) . . ?
C6 C5 H5 120.5 . . ?
C1 C6 S1 119.6(2) . . ?
C5 C6 S1 120.1(2) . . ?
C5 C6 C1 120.2(2) . . ?
C3 C7 H7A 109.5 . . ?
C3 C7 H7B 109.5 . . ?
C3 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N1 C8 H8A 109.5 . . ?
N1 C8 H8B 109.5 . . ?
N1 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
O3 C9 N1 112.56(19) . . ?
C10 C9 O3 123.2(2) . . ?
C10 C9 N1 124.1(2) . . ?
C9 C10 C11 116.9(2) . . ?
C9 C10 C14 120.6(2) . . ?
C11 C10 C14 122.5(2) . . ?
C10 C11 C20 120.2(2) . . ?
C12 C11 C10 119.5(2) . . ?
C12 C11 C20 120.3(2) . . ?
C11 C12 H12 118.5 . . ?
C11 C12 C13 123.0(2) . . ?
C13 C12 H12 118.5 . . ?
O3 C13 C12 115.06(19) . . ?
O4 C13 O3 116.1(2) . . ?
O4 C13 C12 128.9(2) . . ?
C15 C14 C10 119.8(2) . . ?
C19 C14 C10 121.8(2) . . ?
C19 C14 C15 118.4(2) . . ?
C14 C15 H15 119.7 . . ?
C16 C15 C14 120.6(2) . . ?
C16 C15 H15 119.7 . . ?
C15 C16 H16 119.8 . . ?
C17 C16 C15 120.3(2) . . ?
C17 C16 H16 119.8 . . ?
C16 C17 H17 120.1 . . ?
C18 C17 C16 119.8(2) . . ?
C18 C17 H17 120.1 . . ?
C17 C18 H18 119.8 . . ?
C17 C18 C19 120.3(2) . . ?
C19 C18 H18 119.8 . . ?
C14 C19 C18 120.5(2) . . ?
C14 C19 H19 119.7 . . ?
C18 C19 H19 119.7 . . ?
C11 C20 H20A 109.5 . . ?
C11 C20 H20B 109.5 . . ?
C11 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?

_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_180321_syy_11_77_a
_database_code_depnum_ccdc_archive 'CCDC 1831664'
_audit_update_record             
;
2018-03-22 deposited with the CCDC.
2018-11-12 downloaded from the CCDC.
;
_audit_creation_date             2018-03-22
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C33 H26 Cl N O2 S'
_chemical_formula_sum            'C33 H26 Cl N O2 S'
_chemical_formula_weight         536.06
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H O N S Cl'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   10.2302(8)
_cell_length_b                   24.9417(18)
_cell_length_c                   10.5320(7)
_cell_angle_alpha                90
_cell_angle_beta                 94.660(6)
_cell_angle_gamma                90
_cell_volume                     2678.4(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2723
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.3114
_cell_measurement_theta_min      3.0029
_shelx_estimated_absorpt_T_max   0.951
_shelx_estimated_absorpt_T_min   0.906
_exptl_absorpt_coefficient_mu    0.252
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.93763
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.329
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1120
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0349
_diffrn_reflns_av_unetI/netI     0.0445
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            11836
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.346
_diffrn_reflns_theta_min         3.009
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean 10.3592
_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  -41.00   15.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.4683  101.0000 -151.0000 56

#__ type_ start__ end____ width___ exp.time_
  2 omega  -11.00   49.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       11.7808   38.0000    0.0000 60

#__ type_ start__ end____ width___ exp.time_
  3 omega  -11.00   73.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       11.7808   38.0000  120.0000 84
;
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0335795000
_diffrn_orient_matrix_UB_12      -0.0247886000
_diffrn_orient_matrix_UB_13      -0.0032253000
_diffrn_orient_matrix_UB_21      -0.0546517000
_diffrn_orient_matrix_UB_22      -0.0109896000
_diffrn_orient_matrix_UB_23      -0.0368037000
_diffrn_orient_matrix_UB_31      0.0269068000
_diffrn_orient_matrix_UB_32      0.0085789000
_diffrn_orient_matrix_UB_33      -0.0565761000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3528
_reflns_number_total             4895
_reflns_odcompleteness_completeness 99.59
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.199
_refine_diff_density_min         -0.352
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     344
_refine_ls_number_reflns         4895
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0692
_refine_ls_R_factor_gt           0.0439
_refine_ls_restrained_S_all      1.041
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0404P)²+0.6266P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0958
_refine_ls_wR_factor_ref         0.1088
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C8(H8A,H8B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C10(H10), C11(H11), C13(H13), C14(H14), C16(H16), C17(H17), C18(H18),
 C19(H19), C20(H20), C22(H22), C23(H23), C24(H24), C25(H25), C26(H26), C28(H28),
  C29(H29), C31(H31), C32(H32)
2.c Idealised Me refined as rotating group:
 C33(H33A,H33B,H33C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.51138(6) 0.56181(3) -0.23178(5) 0.05455(19) Uani 1 1 d . . . . .
S1 S 0.81896(7) 0.72446(2) 0.62862(6) 0.0557(2) Uani 1 1 d . . . . .
O1 O 0.8368(2) 0.69278(8) 0.74096(15) 0.0742(6) Uani 1 1 d . . . . .
O2 O 0.87526(19) 0.77681(7) 0.6245(2) 0.0802(6) Uani 1 1 d . . . . .
N1 N 0.88250(18) 0.68963(7) 0.51380(17) 0.0481(5) Uani 1 1 d . . . . .
C1 C 0.71406(19) 0.58629(8) 0.31701(19) 0.0378(5) Uani 1 1 d . . . . .
C2 C 0.7267(2) 0.54168(9) 0.39688(19) 0.0392(5) Uani 1 1 d . . . . .
H2 H 0.688719 0.509614 0.367817 0.047 Uiso 1 1 calc R . . . .
C3 C 0.79284(19) 0.54247(8) 0.51767(18) 0.0357(5) Uani 1 1 d . . . . .
C4 C 0.85387(19) 0.59055(9) 0.56402(18) 0.0371(5) Uani 1 1 d . . . . .
C5 C 0.83174(19) 0.63579(8) 0.48685(19) 0.0384(5) Uani 1 1 d . . . . .
C6 C 0.76495(19) 0.63442(9) 0.36593(19) 0.0393(5) Uani 1 1 d . . . . .
C7 C 0.7704(2) 0.68861(9) 0.3031(2) 0.0516(6) Uani 1 1 d . . . . .
H7A H 0.687488 0.707419 0.304384 0.062 Uiso 1 1 calc R . . . .
H7B H 0.793087 0.685477 0.215766 0.062 Uiso 1 1 calc R . . . .
C8 C 0.8790(3) 0.71678(10) 0.3868(2) 0.0616(7) Uani 1 1 d . . . . .
H8A H 0.962638 0.713116 0.350436 0.074 Uiso 1 1 calc R . . . .
H8B H 0.859410 0.754624 0.394871 0.074 Uiso 1 1 calc R . . . .
C9 C 0.65926(19) 0.58068(8) 0.18228(19) 0.0376(5) Uani 1 1 d . . . . .
C10 C 0.6944(2) 0.53687(9) 0.1107(2) 0.0411(5) Uani 1 1 d . . . . .
H10 H 0.750603 0.511216 0.148946 0.049 Uiso 1 1 calc R . . . .
C11 C 0.6485(2) 0.53025(9) -0.0149(2) 0.0427(5) Uani 1 1 d . . . . .
H11 H 0.672289 0.500404 -0.060710 0.051 Uiso 1 1 calc R . . . .
C12 C 0.5664(2) 0.56901(9) -0.07149(19) 0.0408(5) Uani 1 1 d . . . . .
C13 C 0.5280(2) 0.61297(9) -0.0038(2) 0.0451(5) Uani 1 1 d . . . . .
H13 H 0.471695 0.638453 -0.042586 0.054 Uiso 1 1 calc R . . . .
C14 C 0.5745(2) 0.61852(9) 0.1227(2) 0.0446(5) Uani 1 1 d . . . . .
H14 H 0.548896 0.647982 0.168793 0.053 Uiso 1 1 calc R . . . .
C15 C 0.7996(2) 0.49077(9) 0.58961(18) 0.0388(5) Uani 1 1 d . . . . .
C16 C 0.9159(2) 0.46914(9) 0.6460(2) 0.0471(6) Uani 1 1 d . . . . .
H16 H 0.994177 0.487670 0.640846 0.057 Uiso 1 1 calc R . . . .
C17 C 0.9168(3) 0.42078(11) 0.7093(2) 0.0607(7) Uani 1 1 d . . . . .
H17 H 0.995436 0.407223 0.746725 0.073 Uiso 1 1 calc R . . . .
C18 C 0.8024(3) 0.39228(11) 0.7177(2) 0.0687(8) Uani 1 1 d . . . . .
H18 H 0.803323 0.359808 0.761179 0.082 Uiso 1 1 calc R . . . .
C19 C 0.6870(3) 0.41244(11) 0.6611(3) 0.0660(7) Uani 1 1 d . . . . .
H19 H 0.609519 0.393242 0.665263 0.079 Uiso 1 1 calc R . . . .
C20 C 0.6852(2) 0.46102(10) 0.5979(2) 0.0503(6) Uani 1 1 d . . . . .
H20 H 0.606219 0.474130 0.560187 0.060 Uiso 1 1 calc R . . . .
C21 C 0.9433(2) 0.59163(8) 0.68300(19) 0.0388(5) Uani 1 1 d . . . . .
C22 C 1.0735(2) 0.60618(10) 0.6773(2) 0.0487(6) Uani 1 1 d . . . . .
H22 H 1.103376 0.616505 0.599939 0.058 Uiso 1 1 calc R . . . .
C23 C 1.1591(2) 0.60549(11) 0.7856(3) 0.0595(7) Uani 1 1 d . . . . .
H23 H 1.246075 0.615559 0.780688 0.071 Uiso 1 1 calc R . . . .
C24 C 1.1164(3) 0.58992(10) 0.9011(2) 0.0604(7) Uani 1 1 d . . . . .
H24 H 1.174420 0.589304 0.973767 0.072 Uiso 1 1 calc R . . . .
C25 C 0.9884(3) 0.57545(10) 0.9077(2) 0.0570(7) Uani 1 1 d . . . . .
H25 H 0.959271 0.564869 0.985225 0.068 Uiso 1 1 calc R . . . .
C26 C 0.9019(2) 0.57641(10) 0.8000(2) 0.0480(6) Uani 1 1 d . . . . .
H26 H 0.814822 0.566745 0.805928 0.058 Uiso 1 1 calc R . . . .
C27 C 0.6491(2) 0.73000(9) 0.5903(2) 0.0470(6) Uani 1 1 d . . . . .
C28 C 0.5691(3) 0.68731(10) 0.6159(3) 0.0651(7) Uani 1 1 d . . . . .
H28 H 0.604975 0.656433 0.654004 0.078 Uiso 1 1 calc R . . . .
C29 C 0.4363(3) 0.69079(11) 0.5846(3) 0.0700(8) Uani 1 1 d . . . . .
H29 H 0.383182 0.661851 0.601854 0.084 Uiso 1 1 calc R . . . .
C30 C 0.3791(3) 0.73626(11) 0.5280(2) 0.0567(6) Uani 1 1 d . . . . .
C31 C 0.4607(3) 0.77890(10) 0.5055(2) 0.0576(7) Uani 1 1 d . . . . .
H31 H 0.424623 0.810256 0.469963 0.069 Uiso 1 1 calc R . . . .
C32 C 0.5942(3) 0.77581(9) 0.5347(2) 0.0537(6) Uani 1 1 d . . . . .
H32 H 0.647516 0.804605 0.516930 0.064 Uiso 1 1 calc R . . . .
C33 C 0.2333(3) 0.73891(13) 0.4932(3) 0.0786(9) Uani 1 1 d . . . . .
H33A H 0.208729 0.775133 0.471585 0.118 Uiso 1 1 calc GR . . . .
H33B H 0.187445 0.727309 0.564268 0.118 Uiso 1 1 calc GR . . . .
H33C H 0.210874 0.715981 0.421473 0.118 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C12 1.745(2) . ?
S1 O1 1.4221(18) . ?
S1 O2 1.4293(18) . ?
S1 N1 1.664(2) . ?
S1 C27 1.758(2) . ?
N1 C5 1.459(3) . ?
N1 C8 1.497(3) . ?
C1 C2 1.394(3) . ?
C1 C6 1.391(3) . ?
C1 C9 1.489(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.392(3) . ?
C3 C4 1.420(3) . ?
C3 C15 1.494(3) . ?
C4 C5 1.398(3) . ?
C4 C21 1.491(3) . ?
C5 C6 1.396(3) . ?
C6 C7 1.508(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C8 1.532(3) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.391(3) . ?
C9 C14 1.395(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.377(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.384(3) . ?
C12 C13 1.382(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.385(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.394(3) . ?
C15 C20 1.395(3) . ?
C16 H16 0.9300 . ?
C16 C17 1.378(3) . ?
C17 H17 0.9300 . ?
C17 C18 1.378(4) . ?
C18 H18 0.9300 . ?
C18 C19 1.374(4) . ?
C19 H19 0.9300 . ?
C19 C20 1.382(3) . ?
C20 H20 0.9300 . ?
C21 C22 1.386(3) . ?
C21 C26 1.388(3) . ?
C22 H22 0.9300 . ?
C22 C23 1.380(3) . ?
C23 H23 0.9300 . ?
C23 C24 1.381(4) . ?
C24 H24 0.9300 . ?
C24 C25 1.366(4) . ?
C25 H25 0.9300 . ?
C25 C26 1.381(3) . ?
C26 H26 0.9300 . ?
C27 C28 1.382(3) . ?
C27 C32 1.382(3) . ?
C28 H28 0.9300 . ?
C28 C29 1.375(4) . ?
C29 H29 0.9300 . ?
C29 C30 1.388(4) . ?
C30 C31 1.384(3) . ?
C30 C33 1.508(4) . ?
C31 H31 0.9300 . ?
C31 C32 1.378(3) . ?
C32 H32 0.9300 . ?
C33 H33A 0.9600 . ?
C33 H33B 0.9600 . ?
C33 H33C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 S1 O2 120.54(12) . . ?
O1 S1 N1 106.47(10) . . ?
O1 S1 C27 106.99(12) . . ?
O2 S1 N1 105.83(12) . . ?
O2 S1 C27 108.33(11) . . ?
N1 S1 C27 108.16(10) . . ?
C5 N1 S1 117.91(14) . . ?
C5 N1 C8 105.07(17) . . ?
C8 N1 S1 115.52(16) . . ?
C2 C1 C9 120.59(19) . . ?
C6 C1 C2 116.85(19) . . ?
C6 C1 C9 122.33(19) . . ?
C1 C2 H2 118.2 . . ?
C3 C2 C1 123.7(2) . . ?
C3 C2 H2 118.2 . . ?
C2 C3 C4 119.59(19) . . ?
C2 C3 C15 116.77(18) . . ?
C4 C3 C15 123.60(18) . . ?
C3 C4 C21 121.80(19) . . ?
C5 C4 C3 115.83(18) . . ?
C5 C4 C21 122.23(19) . . ?
C4 C5 N1 126.25(18) . . ?
C6 C5 N1 109.88(18) . . ?
C6 C5 C4 123.69(19) . . ?
C1 C6 C5 120.00(19) . . ?
C1 C6 C7 129.57(19) . . ?
C5 C6 C7 110.23(18) . . ?
C6 C7 H7A 111.4 . . ?
C6 C7 H7B 111.4 . . ?
C6 C7 C8 102.09(18) . . ?
H7A C7 H7B 109.2 . . ?
C8 C7 H7A 111.4 . . ?
C8 C7 H7B 111.4 . . ?
N1 C8 C7 105.69(18) . . ?
N1 C8 H8A 110.6 . . ?
N1 C8 H8B 110.6 . . ?
C7 C8 H8A 110.6 . . ?
C7 C8 H8B 110.6 . . ?
H8A C8 H8B 108.7 . . ?
C10 C9 C1 119.75(19) . . ?
C10 C9 C14 117.78(19) . . ?
C14 C9 C1 122.5(2) . . ?
C9 C10 H10 118.9 . . ?
C11 C10 C9 122.1(2) . . ?
C11 C10 H10 118.9 . . ?
C10 C11 H11 120.7 . . ?
C10 C11 C12 118.5(2) . . ?
C12 C11 H11 120.7 . . ?
C11 C12 Cl1 118.79(17) . . ?
C13 C12 Cl1 119.87(17) . . ?
C13 C12 C11 121.3(2) . . ?
C12 C13 H13 120.5 . . ?
C12 C13 C14 119.1(2) . . ?
C14 C13 H13 120.5 . . ?
C9 C14 H14 119.4 . . ?
C13 C14 C9 121.1(2) . . ?
C13 C14 H14 119.4 . . ?
C16 C15 C3 123.57(19) . . ?
C16 C15 C20 117.3(2) . . ?
C20 C15 C3 119.07(19) . . ?
C15 C16 H16 119.4 . . ?
C17 C16 C15 121.1(2) . . ?
C17 C16 H16 119.4 . . ?
C16 C17 H17 119.7 . . ?
C16 C17 C18 120.7(2) . . ?
C18 C17 H17 119.7 . . ?
C17 C18 H18 120.4 . . ?
C19 C18 C17 119.2(3) . . ?
C19 C18 H18 120.4 . . ?
C18 C19 H19 119.8 . . ?
C18 C19 C20 120.5(2) . . ?
C20 C19 H19 119.8 . . ?
C15 C20 H20 119.4 . . ?
C19 C20 C15 121.2(2) . . ?
C19 C20 H20 119.4 . . ?
C22 C21 C4 119.66(18) . . ?
C22 C21 C26 118.2(2) . . ?
C26 C21 C4 122.05(19) . . ?
C21 C22 H22 119.7 . . ?
C23 C22 C21 120.6(2) . . ?
C23 C22 H22 119.7 . . ?
C22 C23 H23 119.8 . . ?
C22 C23 C24 120.4(2) . . ?
C24 C23 H23 119.8 . . ?
C23 C24 H24 120.3 . . ?
C25 C24 C23 119.5(2) . . ?
C25 C24 H24 120.3 . . ?
C24 C25 H25 119.8 . . ?
C24 C25 C26 120.4(2) . . ?
C26 C25 H25 119.8 . . ?
C21 C26 H26 119.6 . . ?
C25 C26 C21 120.8(2) . . ?
C25 C26 H26 119.6 . . ?
C28 C27 S1 118.96(19) . . ?
C32 C27 S1 121.49(19) . . ?
C32 C27 C28 119.5(2) . . ?
C27 C28 H28 120.2 . . ?
C29 C28 C27 119.6(2) . . ?
C29 C28 H28 120.2 . . ?
C28 C29 H29 119.1 . . ?
C28 C29 C30 121.9(2) . . ?
C30 C29 H29 119.1 . . ?
C29 C30 C33 120.9(2) . . ?
C31 C30 C29 117.5(2) . . ?
C31 C30 C33 121.5(3) . . ?
C30 C31 H31 119.4 . . ?
C32 C31 C30 121.3(2) . . ?
C32 C31 H31 119.4 . . ?
C27 C32 H32 119.9 . . ?
C31 C32 C27 120.1(2) . . ?
C31 C32 H32 119.9 . . ?
C30 C33 H33A 109.5 . . ?
C30 C33 H33B 109.5 . . ?
C30 C33 H33C 109.5 . . ?
H33A C33 H33B 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
