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

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

data_200903_sja20200812_2_0ma
_database_code_depnum_ccdc_archive 'CCDC 2040979'
loop_
_audit_author_name
_audit_author_address
'Huajian zhu'
;Zhejiang university city college
China
;
_audit_update_record             
;
2020-10-28 deposited with the CCDC.	2021-02-03 downloaded from the CCDC.
;
_audit_creation_date             2020-09-03
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H16 N2 O5 S'
_chemical_formula_sum            'C18 H16 N2 O5 S'
_chemical_formula_weight         372.39
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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                   8.2430(2)
_cell_length_b                   28.1258(8)
_cell_length_c                   7.5353(2)
_cell_angle_alpha                90
_cell_angle_beta                 105.1650(10)
_cell_angle_gamma                90
_cell_volume                     1686.15(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9436
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      27.10
_cell_measurement_theta_min      2.66
_shelx_estimated_absorpt_T_max   0.944
_shelx_estimated_absorpt_T_min   0.899
_exptl_absorpt_coefficient_mu    0.226
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.7021
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1491 before and 0.0410 after correction.
The Ratio of minimum to maximum transmission is 0.9418.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'light yellow'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.467
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.42
_exptl_crystal_size_min          0.26
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0319
_diffrn_reflns_av_unetI/netI     0.0271
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       36
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            14151
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.113
_diffrn_reflns_theta_min         2.560
_diffrn_ambient_temperature      170.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3463
_reflns_number_total             3723
_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       'SAINT V8.38A (?, 2016)'
_computing_data_collection       'Bruker Instrument Service vV6.2.10'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_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         0.379
_refine_diff_density_min         -0.355
_refine_diff_density_rms         0.071
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         3723
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0393
_refine_ls_R_factor_gt           0.0367
_refine_ls_restrained_S_all      1.065
_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)+(0.0518P)²+0.5713P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0936
_refine_ls_wR_factor_ref         0.0962
_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 Ternary CH refined with riding coordinates:
 C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C4(H4), C5(H5), C14(H14), C15(H15), C17(H17), C18(H18)
2.d X=CH2 refined with riding coordinates:
 C12(H12A,H12B)
2.e Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.65506(4) 0.63174(2) 1.10961(4) 0.02328(11) Uani 1 1 d . . . . .
O1 O 0.80768(12) 0.65862(4) 1.14725(14) 0.0328(2) Uani 1 1 d . . . . .
O2 O 0.63580(13) 0.59423(4) 1.23137(13) 0.0309(2) Uani 1 1 d . . . . .
O3 O 0.34412(12) 0.63409(3) 0.66913(14) 0.0276(2) Uani 1 1 d . . . . .
O4 O -0.04951(16) 0.42475(4) 0.16449(17) 0.0464(3) Uani 1 1 d . . . . .
O5 O -0.18703(13) 0.48779(4) 0.05089(14) 0.0371(3) Uani 1 1 d . . . . .
N1 N 0.63477(14) 0.60592(4) 0.90791(15) 0.0235(2) Uani 1 1 d . . . . .
N2 N -0.06850(15) 0.46782(4) 0.15830(16) 0.0297(3) Uani 1 1 d . . . . .
C1 C 0.50461(18) 0.71897(5) 1.0470(2) 0.0291(3) Uani 1 1 d . . . . .
H1 H 0.608498 0.730372 1.031387 0.035 Uiso 1 1 calc R . . . .
C2 C 0.36969(19) 0.74950(5) 1.0286(2) 0.0325(3) Uani 1 1 d . . . . .
H2 H 0.381671 0.781955 0.999389 0.039 Uiso 1 1 calc R . . . .
C3 C 0.21669(18) 0.73362(5) 1.05202(18) 0.0287(3) Uani 1 1 d . . . . .
C4 C 0.20079(17) 0.68569(5) 1.09280(18) 0.0271(3) Uani 1 1 d . . . . .
H4 H 0.097093 0.674358 1.109154 0.033 Uiso 1 1 calc R . . . .
C5 C 0.33398(16) 0.65435(5) 1.10983(18) 0.0244(3) Uani 1 1 d . . . . .
H5 H 0.321323 0.621706 1.135692 0.029 Uiso 1 1 calc R . . . .
C6 C 0.48657(15) 0.67136(4) 1.08850(16) 0.0221(2) Uani 1 1 d . . . . .
C7 C 0.0724(2) 0.76767(6) 1.0369(2) 0.0409(4) Uani 1 1 d . . . . .
H7A H -0.024219 0.750500 1.058154 0.061 Uiso 1 1 calc GR . . . .
H7B H 0.041479 0.781771 0.913647 0.061 Uiso 1 1 calc GR . . . .
H7C H 0.106210 0.792879 1.128931 0.061 Uiso 1 1 calc GR . . . .
C8 C 0.64799(17) 0.63354(4) 0.75158(18) 0.0247(3) Uani 1 1 d . . . . .
C9 C 0.49233(17) 0.62492(4) 0.60514(18) 0.0254(3) Uani 1 1 d . . . . .
H9 H 0.489927 0.629310 0.472787 0.030 Uiso 1 1 calc R . . . .
C10 C 0.39913(16) 0.58564(4) 0.66305(17) 0.0222(3) Uani 1 1 d . . . . .
C11 C 0.50175(16) 0.56901(5) 0.84963(18) 0.0255(3) Uani 1 1 d . . . . .
H11A H 0.431378 0.567040 0.937604 0.031 Uiso 1 1 calc R . . . .
H11B H 0.552009 0.537421 0.840704 0.031 Uiso 1 1 calc R . . . .
C12 C 0.7770(2) 0.65960(6) 0.7360(2) 0.0362(3) Uani 1 1 d . . . . .
H12A H 0.875161 0.661483 0.835548 0.043 Uiso 1 1 calc R . . . .
H12B H 0.771533 0.676442 0.625353 0.043 Uiso 1 1 calc R . . . .
C13 C 0.28068(15) 0.55392(4) 0.53161(17) 0.0220(3) Uani 1 1 d . . . . .
C14 C 0.14689(17) 0.57450(5) 0.40044(18) 0.0260(3) Uani 1 1 d . . . . .
H14 H 0.133731 0.608066 0.396415 0.031 Uiso 1 1 calc R . . . .
C15 C 0.03394(16) 0.54643(5) 0.27693(18) 0.0270(3) Uani 1 1 d . . . . .
H15 H -0.056463 0.560300 0.187011 0.032 Uiso 1 1 calc R . . . .
C16 C 0.05527(16) 0.49758(5) 0.28693(17) 0.0242(3) Uani 1 1 d . . . . .
C17 C 0.18522(16) 0.47587(5) 0.41507(18) 0.0251(3) Uani 1 1 d . . . . .
H17 H 0.196625 0.442244 0.418808 0.030 Uiso 1 1 calc R . . . .
C18 C 0.29864(16) 0.50448(4) 0.53817(18) 0.0241(3) Uani 1 1 d . . . . .
H18 H 0.389000 0.490369 0.627406 0.029 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O1 1.4311(10) . ?
S1 O2 1.4339(10) . ?
S1 N1 1.6530(11) . ?
S1 C6 1.7551(13) . ?
O3 C9 1.4490(16) . ?
O3 C10 1.4407(14) . ?
O4 N2 1.2208(17) . ?
O5 N2 1.2294(16) . ?
N1 C8 1.4387(16) . ?
N1 C11 1.4903(16) . ?
N2 C16 1.4710(16) . ?
C1 H1 0.9500 . ?
C1 C2 1.383(2) . ?
C1 C6 1.3920(18) . ?
C2 H2 0.9500 . ?
C2 C3 1.392(2) . ?
C3 C4 1.397(2) . ?
C3 C7 1.5078(19) . ?
C4 H4 0.9500 . ?
C4 C5 1.3875(18) . ?
C5 H5 0.9500 . ?
C5 C6 1.3937(17) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 C9 1.4771(19) . ?
C8 C12 1.3216(19) . ?
C9 H9 1.0000 . ?
C9 C10 1.4754(17) . ?
C10 C11 1.5129(17) . ?
C10 C13 1.4914(17) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 H12A 0.9500 . ?
C12 H12B 0.9500 . ?
C13 C14 1.3992(18) . ?
C13 C18 1.3978(17) . ?
C14 H14 0.9500 . ?
C14 C15 1.3795(19) . ?
C15 H15 0.9500 . ?
C15 C16 1.3847(19) . ?
C16 C17 1.3825(19) . ?
C17 H17 0.9500 . ?
C17 C18 1.3887(18) . ?
C18 H18 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 S1 O2 120.04(6) . . ?
O1 S1 N1 106.65(6) . . ?
O1 S1 C6 108.44(6) . . ?
O2 S1 N1 105.29(6) . . ?
O2 S1 C6 107.92(6) . . ?
N1 S1 C6 107.95(6) . . ?
C10 O3 C9 61.40(8) . . ?
C8 N1 S1 120.30(9) . . ?
C8 N1 C11 110.02(10) . . ?
C11 N1 S1 117.82(8) . . ?
O4 N2 O5 123.40(12) . . ?
O4 N2 C16 118.65(12) . . ?
O5 N2 C16 117.94(12) . . ?
C2 C1 H1 120.3 . . ?
C2 C1 C6 119.30(13) . . ?
C6 C1 H1 120.3 . . ?
C1 C2 H2 119.3 . . ?
C1 C2 C3 121.30(13) . . ?
C3 C2 H2 119.3 . . ?
C2 C3 C4 118.55(12) . . ?
C2 C3 C7 120.63(13) . . ?
C4 C3 C7 120.81(14) . . ?
C3 C4 H4 119.5 . . ?
C5 C4 C3 121.07(12) . . ?
C5 C4 H4 119.5 . . ?
C4 C5 H5 120.4 . . ?
C4 C5 C6 119.17(12) . . ?
C6 C5 H5 120.4 . . ?
C1 C6 S1 120.17(10) . . ?
C1 C6 C5 120.59(12) . . ?
C5 C6 S1 119.23(10) . . ?
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 C9 106.62(11) . . ?
C12 C8 N1 127.37(13) . . ?
C12 C8 C9 125.91(13) . . ?
O3 C9 C8 111.44(11) . . ?
O3 C9 H9 120.8 . . ?
O3 C9 C10 59.02(8) . . ?
C8 C9 H9 120.8 . . ?
C10 C9 C8 108.65(11) . . ?
C10 C9 H9 120.8 . . ?
O3 C10 C9 59.58(8) . . ?
O3 C10 C11 111.53(10) . . ?
O3 C10 C13 115.48(10) . . ?
C9 C10 C11 107.37(11) . . ?
C9 C10 C13 123.55(11) . . ?
C13 C10 C11 122.82(11) . . ?
N1 C11 C10 104.35(10) . . ?
N1 C11 H11A 110.9 . . ?
N1 C11 H11B 110.9 . . ?
C10 C11 H11A 110.9 . . ?
C10 C11 H11B 110.9 . . ?
H11A C11 H11B 108.9 . . ?
C8 C12 H12A 120.0 . . ?
C8 C12 H12B 120.0 . . ?
H12A C12 H12B 120.0 . . ?
C14 C13 C10 118.67(11) . . ?
C18 C13 C10 121.78(11) . . ?
C18 C13 C14 119.54(12) . . ?
C13 C14 H14 119.7 . . ?
C15 C14 C13 120.53(12) . . ?
C15 C14 H14 119.7 . . ?
C14 C15 H15 120.7 . . ?
C14 C15 C16 118.52(12) . . ?
C16 C15 H15 120.7 . . ?
C15 C16 N2 118.19(12) . . ?
C17 C16 N2 119.08(12) . . ?
C17 C16 C15 122.71(12) . . ?
C16 C17 H17 120.9 . . ?
C16 C17 C18 118.28(12) . . ?
C18 C17 H17 120.9 . . ?
C13 C18 H18 119.8 . . ?
C17 C18 C13 120.42(12) . . ?
C17 C18 H18 119.8 . . ?

_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_200903_sja20200812_1_0m
_database_code_depnum_ccdc_archive 'CCDC 2040984'
loop_
_audit_author_name
_audit_author_address
'Huajian zhu'
;Zhejiang Universtiy City College
China
;
_audit_update_record             
;
2020-10-28 deposited with the CCDC.	2021-02-03 downloaded from the CCDC.
;
_audit_creation_date             2020-09-03
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H21 N O3 S2'
_chemical_formula_sum            'C20 H21 N O3 S2'
_chemical_formula_weight         387.50
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   14.1295(4)
_cell_length_b                   9.5636(3)
_cell_length_c                   14.5227(4)
_cell_angle_alpha                90
_cell_angle_beta                 102.4220(10)
_cell_angle_gamma                90
_cell_volume                     1916.49(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9870
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      27.11
_cell_measurement_theta_min      2.80
_shelx_estimated_absorpt_T_max   0.946
_shelx_estimated_absorpt_T_min   0.875
_exptl_absorpt_coefficient_mu    0.297
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6772
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1227 before and 0.0629 after correction.
The Ratio of minimum to maximum transmission is 0.9084.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.343
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.19
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0277
_diffrn_reflns_av_unetI/netI     0.0196
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            29095
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.112
_diffrn_reflns_theta_min         2.569
_diffrn_ambient_temperature      170.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3884
_reflns_number_total             4226
_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       'SAINT V8.38A (?, 2016)'
_computing_data_collection       'Bruker Instrument Service vV6.2.10'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_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         0.454
_refine_diff_density_min         -0.316
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     239
_refine_ls_number_reflns         4226
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0338
_refine_ls_R_factor_gt           0.0308
_refine_ls_restrained_S_all      1.051
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0416P)²+0.9375P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0852
_refine_ls_wR_factor_ref         0.0878
_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), C11(H11), C15(H15), C16(H16), C18(H18),
 C19(H19)
2.b Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C12(H12A,H12B,H12C), C13(H13A,H13B,H13C), C20(H20A,H20B,H20C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.81374(2) 0.81993(3) 0.37262(2) 0.02473(10) Uani 1 1 d . . . . .
S2 S 0.50025(3) 0.74557(4) 0.08105(3) 0.03477(11) Uani 1 1 d . . . . .
O1 O 0.86901(7) 0.90502(11) 0.32255(8) 0.0337(2) Uani 1 1 d . . . . .
O2 O 0.80384(7) 0.85896(11) 0.46500(7) 0.0329(2) Uani 1 1 d . . . . .
O3 O 0.15811(7) 0.78025(11) 0.34334(8) 0.0327(2) Uani 1 1 d . . . . .
N1 N 0.70041(8) 0.81414(12) 0.30932(8) 0.0250(2) Uani 1 1 d . . . . .
C1 C 0.81589(11) 0.54545(16) 0.42066(12) 0.0361(3) Uani 1 1 d . . . . .
H1 H 0.762504 0.566706 0.448341 0.043 Uiso 1 1 calc R . . . .
C2 C 0.85335(12) 0.41125(16) 0.42520(13) 0.0390(4) Uani 1 1 d . . . . .
H2 H 0.824530 0.340012 0.455611 0.047 Uiso 1 1 calc R . . . .
C3 C 0.93220(10) 0.37854(15) 0.38622(10) 0.0291(3) Uani 1 1 d . . . . .
C4 C 0.97316(11) 0.48385(16) 0.34221(11) 0.0339(3) Uani 1 1 d . . . . .
H4 H 1.027589 0.463306 0.315899 0.041 Uiso 1 1 calc R . . . .
C5 C 0.93628(10) 0.61877(15) 0.33579(11) 0.0310(3) Uani 1 1 d . . . . .
H5 H 0.964674 0.689884 0.304875 0.037 Uiso 1 1 calc R . . . .
C6 C 0.85762(9) 0.64830(14) 0.37502(9) 0.0239(3) Uani 1 1 d . . . . .
C7 C 0.97191(13) 0.23206(16) 0.39046(12) 0.0392(4) Uani 1 1 d . . . . .
H7A H 0.937816 0.179177 0.335462 0.059 Uiso 1 1 calc GR . . . .
H7B H 0.962532 0.186244 0.448198 0.059 Uiso 1 1 calc GR . . . .
H7C H 1.041241 0.235412 0.390497 0.059 Uiso 1 1 calc GR . . . .
C8 C 0.67003(10) 0.79300(14) 0.21197(9) 0.0267(3) Uani 1 1 d . . . . .
C9 C 0.57164(10) 0.77536(14) 0.19426(9) 0.0261(3) Uani 1 1 d . . . . .
C10 C 0.53959(10) 0.78487(14) 0.28217(10) 0.0249(3) Uani 1 1 d . . . . .
C11 C 0.61985(10) 0.80754(14) 0.35091(10) 0.0258(3) Uani 1 1 d . . . . .
H11 H 0.621142 0.817290 0.416269 0.031 Uiso 1 1 calc R . . . .
C12 C 0.73722(11) 0.79555(19) 0.14586(11) 0.0370(3) Uani 1 1 d . . . . .
H12A H 0.769869 0.886455 0.149898 0.055 Uiso 1 1 calc GR . . . .
H12B H 0.700374 0.780566 0.081312 0.055 Uiso 1 1 calc GR . . . .
H12C H 0.785641 0.721323 0.162854 0.055 Uiso 1 1 calc GR . . . .
C13 C 0.42316(13) 0.8978(2) 0.06549(13) 0.0477(4) Uani 1 1 d . . . . .
H13A H 0.382414 0.897600 0.001692 0.072 Uiso 1 1 calc GR . . . .
H13B H 0.463246 0.982351 0.074552 0.072 Uiso 1 1 calc GR . . . .
H13C H 0.381901 0.896093 0.111775 0.072 Uiso 1 1 calc GR . . . .
C14 C 0.43972(10) 0.78255(14) 0.29776(9) 0.0253(3) Uani 1 1 d . . . . .
C15 C 0.37220(10) 0.67960(15) 0.25957(10) 0.0299(3) Uani 1 1 d . . . . .
H15 H 0.390273 0.607543 0.221734 0.036 Uiso 1 1 calc R . . . .
C16 C 0.27936(10) 0.68160(15) 0.27632(11) 0.0305(3) Uani 1 1 d . . . . .
H16 H 0.234337 0.610961 0.250017 0.037 Uiso 1 1 calc R . . . .
C17 C 0.25166(10) 0.78655(15) 0.33150(10) 0.0257(3) Uani 1 1 d . . . . .
C18 C 0.31804(10) 0.88865(15) 0.37107(10) 0.0287(3) Uani 1 1 d . . . . .
H18 H 0.300158 0.959812 0.409684 0.034 Uiso 1 1 calc R . . . .
C19 C 0.41088(10) 0.88544(15) 0.35349(10) 0.0285(3) Uani 1 1 d . . . . .
H19 H 0.455981 0.955661 0.380376 0.034 Uiso 1 1 calc R . . . .
C20 C 0.12751(11) 0.89338(17) 0.39372(12) 0.0370(3) Uani 1 1 d . . . . .
H20A H 0.136221 0.981699 0.362340 0.056 Uiso 1 1 calc GR . . . .
H20B H 0.166300 0.894780 0.458357 0.056 Uiso 1 1 calc GR . . . .
H20C H 0.058942 0.881499 0.395131 0.056 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 1.4301(11) . ?
S1 O2 1.4282(10) . ?
S1 N1 1.6670(11) . ?
S1 C6 1.7523(13) . ?
S2 C9 1.7573(14) . ?
S2 C13 1.8029(18) . ?
O3 C17 1.3705(16) . ?
O3 C20 1.4244(18) . ?
N1 C8 1.4010(17) . ?
N1 C11 1.4001(17) . ?
C1 H1 0.9500 . ?
C1 C2 1.384(2) . ?
C1 C6 1.387(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.390(2) . ?
C3 C4 1.384(2) . ?
C3 C7 1.505(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.387(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.3828(19) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 C9 1.3687(19) . ?
C8 C12 1.4886(19) . ?
C9 C10 1.4465(19) . ?
C10 C11 1.3574(19) . ?
C10 C14 1.4766(18) . ?
C11 H11 0.9500 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 C15 1.3998(19) . ?
C14 C19 1.3897(19) . ?
C15 H15 0.9500 . ?
C15 C16 1.385(2) . ?
C16 H16 0.9500 . ?
C16 C17 1.392(2) . ?
C17 C18 1.3898(19) . ?
C18 H18 0.9500 . ?
C18 C19 1.3895(19) . ?
C19 H19 0.9500 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?

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 107.66(6) . . ?
O1 S1 C6 108.27(6) . . ?
O2 S1 O1 120.23(7) . . ?
O2 S1 N1 104.49(6) . . ?
O2 S1 C6 109.38(6) . . ?
N1 S1 C6 105.88(6) . . ?
C9 S2 C13 101.31(8) . . ?
C17 O3 C20 116.02(11) . . ?
C8 N1 S1 127.64(10) . . ?
C11 N1 S1 122.50(9) . . ?
C11 N1 C8 109.13(11) . . ?
C2 C1 H1 120.6 . . ?
C2 C1 C6 118.88(13) . . ?
C6 C1 H1 120.6 . . ?
C1 C2 H2 119.3 . . ?
C1 C2 C3 121.41(14) . . ?
C3 C2 H2 119.3 . . ?
C2 C3 C7 121.15(14) . . ?
C4 C3 C2 118.40(13) . . ?
C4 C3 C7 120.45(13) . . ?
C3 C4 H4 119.4 . . ?
C3 C4 C5 121.30(13) . . ?
C5 C4 H4 119.4 . . ?
C4 C5 H5 120.5 . . ?
C6 C5 C4 119.07(13) . . ?
C6 C5 H5 120.5 . . ?
C1 C6 S1 119.28(10) . . ?
C5 C6 S1 119.70(11) . . ?
C5 C6 C1 120.94(13) . . ?
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 C12 123.30(13) . . ?
C9 C8 N1 106.61(12) . . ?
C9 C8 C12 130.07(13) . . ?
C8 C9 S2 123.45(11) . . ?
C8 C9 C10 108.94(12) . . ?
C10 C9 S2 127.62(11) . . ?
C9 C10 C14 128.71(12) . . ?
C11 C10 C9 106.77(12) . . ?
C11 C10 C14 124.37(12) . . ?
N1 C11 H11 125.7 . . ?
C10 C11 N1 108.55(12) . . ?
C10 C11 H11 125.7 . . ?
C8 C12 H12A 109.5 . . ?
C8 C12 H12B 109.5 . . ?
C8 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
S2 C13 H13A 109.5 . . ?
S2 C13 H13B 109.5 . . ?
S2 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C15 C14 C10 122.84(12) . . ?
C19 C14 C10 119.22(12) . . ?
C19 C14 C15 117.94(12) . . ?
C14 C15 H15 119.6 . . ?
C16 C15 C14 120.75(13) . . ?
C16 C15 H15 119.6 . . ?
C15 C16 H16 119.8 . . ?
C15 C16 C17 120.36(13) . . ?
C17 C16 H16 119.8 . . ?
O3 C17 C16 116.03(12) . . ?
O3 C17 C18 124.22(13) . . ?
C18 C17 C16 119.75(13) . . ?
C17 C18 H18 120.4 . . ?
C19 C18 C17 119.23(13) . . ?
C19 C18 H18 120.4 . . ?
C14 C19 H19 119.0 . . ?
C18 C19 C14 121.96(13) . . ?
C18 C19 H19 119.0 . . ?
O3 C20 H20A 109.5 . . ?
O3 C20 H20B 109.5 . . ?
O3 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'
