# 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_200720_zlw_12_22_25_0ma
_database_code_depnum_ccdc_archive 'CCDC 2045517'
loop_
_audit_author_name
_audit_author_address
'linwei Zeng'
;zhejiang university
China
;
_audit_update_record             
;
2020-11-20 deposited with the CCDC.	2021-06-03 downloaded from the CCDC.
;
_audit_creation_date             2020-07-21
_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         'C15 H15 N O4 S2'
_chemical_formula_sum            'C15 H15 N O4 S2'
_chemical_formula_weight         337.40
_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                   17.0004(4)
_cell_length_b                   11.7535(3)
_cell_length_c                   7.8717(2)
_cell_angle_alpha                90
_cell_angle_beta                 102.6240(10)
_cell_angle_gamma                90
_cell_volume                     1534.85(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9949
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      32.81
_cell_measurement_theta_min      2.46
_shelx_estimated_absorpt_T_max   0.931
_shelx_estimated_absorpt_T_min   0.845
_exptl_absorpt_coefficient_mu    0.364
_exptl_absorpt_correction_T_max  0.7466
_exptl_absorpt_correction_T_min  0.7082
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0757 before and 0.0458 after correction.
The Ratio of minimum to maximum transmission is 0.9486.
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    1.460
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0254
_diffrn_reflns_av_unetI/netI     0.0158
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            26119
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.484
_diffrn_reflns_theta_min         2.455
_diffrn_ambient_temperature      170.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'zju Bruker D8 Venture Ims3.0'
_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                3263
_reflns_number_total             3520
_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
_computing.data_collection       Bruker
_computing.data_reduction        SAINT
_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         0.262
_refine_diff_density_min         -0.351
_refine_diff_density_rms         0.059
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         3520
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0320
_refine_ls_R_factor_gt           0.0296
_refine_ls_restrained_S_all      1.060
_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)+(0.0332P)²+0.7956P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0756
_refine_ls_wR_factor_ref         0.0778
_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)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C9(H9), C10(H10), C12(H12), C13(H13)
2.c Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C15(H15A,H15B,H15C)
;
_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 -0.04992(2) 0.28091(3) 0.58009(6) 0.03768(11) Uani 1 1 d . . . . .
S2 S 0.32447(2) 0.42274(3) 0.48945(4) 0.02178(9) Uani 1 1 d . . . . .
O1 O 0.11872(6) 0.24282(9) 0.62451(16) 0.0376(3) Uani 1 1 d . . . . .
O2 O 0.30803(6) 0.41463(10) 0.86480(13) 0.0376(3) Uani 1 1 d . . . . .
O3 O 0.30611(6) 0.53949(8) 0.52068(14) 0.0308(2) Uani 1 1 d . . . . .
O4 O 0.31169(6) 0.38340(9) 0.31202(12) 0.0313(2) Uani 1 1 d . . . . .
N1 N 0.17216(6) 0.39557(9) 0.78659(14) 0.0236(2) Uani 1 1 d . . . . .
C1 C -0.12389(9) 0.37548(17) 0.5956(2) 0.0435(4) Uani 1 1 d . . . . .
H1 H -0.179816 0.360816 0.555211 0.052 Uiso 1 1 calc R . . . .
C2 C -0.09371(10) 0.47401(16) 0.6722(2) 0.0410(4) Uani 1 1 d . . . . .
H2 H -0.126320 0.536401 0.690911 0.049 Uiso 1 1 calc R . . . .
C3 C -0.00857(9) 0.47437(13) 0.72158(18) 0.0320(3) Uani 1 1 d . . . . .
H3 H 0.022313 0.536970 0.776082 0.038 Uiso 1 1 calc R . . . .
C4 C 0.02443(8) 0.37345(11) 0.68146(16) 0.0248(3) Uani 1 1 d . . . . .
C5 C 0.10736(8) 0.33206(11) 0.69494(17) 0.0248(3) Uani 1 1 d . . . . .
C6 C 0.25035(8) 0.38147(12) 0.75784(17) 0.0253(3) Uani 1 1 d . . . . .
C7 C 0.26057(7) 0.33355(11) 0.58585(16) 0.0239(2) Uani 1 1 d . . . . .
H7A H 0.207126 0.326894 0.505552 0.029 Uiso 1 1 calc R . . . .
H7B H 0.284312 0.256432 0.604365 0.029 Uiso 1 1 calc R . . . .
C8 C 0.42468(7) 0.39328(11) 0.59399(16) 0.0210(2) Uani 1 1 d . . . . .
C9 C 0.46129(8) 0.29473(11) 0.55094(17) 0.0246(3) Uani 1 1 d . . . . .
H9 H 0.432540 0.243014 0.467148 0.030 Uiso 1 1 calc R . . . .
C10 C 0.54070(8) 0.27385(11) 0.63325(17) 0.0266(3) Uani 1 1 d . . . . .
H10 H 0.566293 0.206647 0.605478 0.032 Uiso 1 1 calc R . . . .
C11 C 0.58391(8) 0.34908(12) 0.75579(17) 0.0259(3) Uani 1 1 d . . . . .
C12 C 0.54590(8) 0.44773(12) 0.79470(18) 0.0281(3) Uani 1 1 d . . . . .
H12 H 0.574865 0.500199 0.876936 0.034 Uiso 1 1 calc R . . . .
C13 C 0.46641(8) 0.47027(11) 0.71497(17) 0.0262(3) Uani 1 1 d . . . . .
H13 H 0.440738 0.537438 0.742597 0.031 Uiso 1 1 calc R . . . .
C14 C 0.67009(8) 0.32389(14) 0.8436(2) 0.0365(3) Uani 1 1 d . . . . .
H14A H 0.705322 0.341714 0.763915 0.055 Uiso 1 1 calc GR . . . .
H14B H 0.675427 0.243155 0.875127 0.055 Uiso 1 1 calc GR . . . .
H14C H 0.685597 0.370421 0.948940 0.055 Uiso 1 1 calc GR . . . .
C15 C 0.16620(9) 0.46795(12) 0.93601(18) 0.0297(3) Uani 1 1 d . . . . .
H15A H 0.165911 0.548148 0.901817 0.045 Uiso 1 1 calc GR . . . .
H15B H 0.212482 0.453545 1.032177 0.045 Uiso 1 1 calc GR . . . .
H15C H 0.116249 0.450314 0.973450 0.045 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 C1 1.7026(17) . ?
S1 C4 1.7252(14) . ?
S2 O3 1.4403(10) . ?
S2 O4 1.4419(10) . ?
S2 C7 1.7930(13) . ?
S2 C8 1.7570(13) . ?
O1 C5 1.2213(17) . ?
O2 C6 1.2089(16) . ?
N1 C5 1.3942(16) . ?
N1 C6 1.4061(16) . ?
N1 C15 1.4729(17) . ?
C1 H1 0.9500 . ?
C1 C2 1.354(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.414(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.3780(19) . ?
C4 C5 1.4731(17) . ?
C6 C7 1.5110(18) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.3914(17) . ?
C8 C13 1.3905(17) . ?
C9 H9 0.9500 . ?
C9 C10 1.3857(18) . ?
C10 H10 0.9500 . ?
C10 C11 1.3937(19) . ?
C11 C12 1.394(2) . ?
C11 C14 1.5064(18) . ?
C12 H12 0.9500 . ?
C12 C13 1.3855(18) . ?
C13 H13 0.9500 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 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
C1 S1 C4 91.91(8) . . ?
O3 S2 O4 118.59(6) . . ?
O3 S2 C7 108.11(6) . . ?
O3 S2 C8 109.39(6) . . ?
O4 S2 C7 104.21(6) . . ?
O4 S2 C8 108.41(6) . . ?
C8 S2 C7 107.56(6) . . ?
C5 N1 C6 121.43(11) . . ?
C5 N1 C15 122.55(11) . . ?
C6 N1 C15 115.40(11) . . ?
S1 C1 H1 123.9 . . ?
C2 C1 S1 112.11(12) . . ?
C2 C1 H1 123.9 . . ?
C1 C2 H2 123.5 . . ?
C1 C2 C3 112.99(14) . . ?
C3 C2 H2 123.5 . . ?
C2 C3 H3 123.9 . . ?
C4 C3 C2 112.20(14) . . ?
C4 C3 H3 123.9 . . ?
C3 C4 S1 110.79(10) . . ?
C3 C4 C5 134.33(13) . . ?
C5 C4 S1 114.71(10) . . ?
O1 C5 N1 120.62(12) . . ?
O1 C5 C4 119.65(12) . . ?
N1 C5 C4 119.73(11) . . ?
O2 C6 N1 120.09(12) . . ?
O2 C6 C7 120.64(12) . . ?
N1 C6 C7 119.08(11) . . ?
S2 C7 H7A 109.4 . . ?
S2 C7 H7B 109.4 . . ?
C6 C7 S2 111.11(9) . . ?
C6 C7 H7A 109.4 . . ?
C6 C7 H7B 109.4 . . ?
H7A C7 H7B 108.0 . . ?
C9 C8 S2 119.31(10) . . ?
C13 C8 S2 119.33(10) . . ?
C13 C8 C9 121.35(12) . . ?
C8 C9 H9 120.8 . . ?
C10 C9 C8 118.39(12) . . ?
C10 C9 H9 120.8 . . ?
C9 C10 H10 119.2 . . ?
C9 C10 C11 121.57(12) . . ?
C11 C10 H10 119.2 . . ?
C10 C11 C12 118.71(12) . . ?
C10 C11 C14 120.37(13) . . ?
C12 C11 C14 120.92(13) . . ?
C11 C12 H12 119.6 . . ?
C13 C12 C11 120.85(12) . . ?
C13 C12 H12 119.6 . . ?
C8 C13 H13 120.4 . . ?
C12 C13 C8 119.13(12) . . ?
C12 C13 H13 120.4 . . ?
C11 C14 H14A 109.5 . . ?
C11 C14 H14B 109.5 . . ?
C11 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N1 C15 H15A 109.5 . . ?
N1 C15 H15B 109.5 . . ?
N1 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 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_200629_zlw_12_100_0m
_database_code_depnum_ccdc_archive 'CCDC 2045518'
loop_
_audit_author_name
_audit_author_address
'linwei Zeng'
;zhejiang university
China
;
_audit_update_record             
;
2020-11-20 deposited with the CCDC.	2021-06-03 downloaded from the CCDC.
;
_audit_creation_date             2020-06-29
_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         'C22 H22 N2 O7 S'
_chemical_formula_sum            'C22 H22 N2 O7 S'
_chemical_formula_weight         458.47
_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      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                   7.266(3)
_cell_length_b                   11.193(4)
_cell_length_c                   14.501(5)
_cell_angle_alpha                70.164(13)
_cell_angle_beta                 79.380(16)
_cell_angle_gamma                81.797(18)
_cell_volume                     1086.2(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9956
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      27.09
_cell_measurement_theta_min      2.82
_shelx_estimated_absorpt_T_max   0.986
_shelx_estimated_absorpt_T_min   0.929
_exptl_absorpt_coefficient_mu    0.196
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.7160
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0682 before and 0.0390 after correction.
The Ratio of minimum to maximum transmission is 0.9604.
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    1.402
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             480
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.07
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0254
_diffrn_reflns_av_unetI/netI     0.0265
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            18134
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.114
_diffrn_reflns_theta_min         2.817
_diffrn_ambient_temperature      170.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'zju Bruker D8 Venture Ims3.0'
_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                4349
_reflns_number_total             4787
_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       ?
_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         0.471
_refine_diff_density_min         -0.556
_refine_diff_density_rms         0.053
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     293
_refine_ls_number_reflns         4787
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0391
_refine_ls_R_factor_gt           0.0356
_refine_ls_restrained_S_all      1.060
_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)+(0.0375P)²+0.5180P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0880
_refine_ls_wR_factor_ref         0.0909
_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:
 C12(H12A,H12B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C14(H14), C15(H15), C17(H17), C18(H18)
2.c Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C20(H20A,H20B,H20C), C21(H21A,H21B,H21C), C22(H22A,H22B,
 H22C)
;
_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 0.30001(5) 0.35831(3) 1.04412(2) 0.02605(10) Uani 1 1 d . . . . .
O1 O 0.56107(14) 0.65818(9) 0.56159(7) 0.0321(2) Uani 1 1 d . . . . .
O2 O 0.20678(14) 0.60353(9) 0.53840(7) 0.0268(2) Uani 1 1 d . . . . .
O3 O 0.23393(14) 0.64497(8) 0.75180(7) 0.0263(2) Uani 1 1 d . . . . .
O4 O 0.48822(16) 0.29627(10) 0.86181(8) 0.0389(3) Uani 1 1 d . . . . .
O5 O 0.17754(17) 0.42974(10) 1.10097(7) 0.0366(3) Uani 1 1 d . . . . .
O6 O 0.49341(16) 0.32859(10) 1.05957(8) 0.0380(3) Uani 1 1 d . . . . .
O7 O 0.06153(15) 0.81689(11) 0.39106(8) 0.0352(2) Uani 1 1 d . . . . .
N1 N 0.28006(16) 0.72067(10) 0.49874(8) 0.0247(2) Uani 1 1 d . . . . .
N2 N 0.33392(16) 0.44453(10) 0.74643(8) 0.0241(2) Uani 1 1 d . . . . .
C1 C 0.6519(2) 0.93538(14) 0.41851(10) 0.0297(3) Uani 1 1 d . . . . .
H1 H 0.757715 0.901884 0.452250 0.036 Uiso 1 1 calc R . . . .
C2 C 0.6449(2) 1.05686(15) 0.34769(11) 0.0352(3) Uani 1 1 d . . . . .
H2 H 0.748658 1.106589 0.332563 0.042 Uiso 1 1 calc R . . . .
C3 C 0.4898(2) 1.10629(14) 0.29909(11) 0.0362(3) Uani 1 1 d . . . . .
H3 H 0.488235 1.189738 0.252312 0.043 Uiso 1 1 calc R . . . .
C4 C 0.3361(2) 1.03559(14) 0.31773(10) 0.0318(3) Uani 1 1 d . . . . .
H4 H 0.230014 1.068903 0.284210 0.038 Uiso 1 1 calc R . . . .
C5 C 0.34416(19) 0.91496(13) 0.38697(9) 0.0251(3) Uani 1 1 d . . . . .
C6 C 0.49862(19) 0.86634(12) 0.43720(9) 0.0244(3) Uani 1 1 d . . . . .
C7 C 0.46329(19) 0.73659(12) 0.50752(9) 0.0240(3) Uani 1 1 d . . . . .
C8 C 0.20518(19) 0.81814(13) 0.42066(9) 0.0255(3) Uani 1 1 d . . . . .
C9 C 0.09530(19) 0.58561(13) 0.63764(9) 0.0249(3) Uani 1 1 d . . . . .
C10 C 0.22970(18) 0.56377(12) 0.71483(9) 0.0214(2) Uani 1 1 d . . . . .
C11 C 0.38164(19) 0.39173(12) 0.84189(10) 0.0243(3) Uani 1 1 d . . . . .
C12 C 0.28534(19) 0.45302(12) 0.91843(9) 0.0231(3) Uani 1 1 d . . . . .
H12A H 0.151004 0.474268 0.910335 0.028 Uiso 1 1 calc R . . . .
H12B H 0.341094 0.534060 0.904900 0.028 Uiso 1 1 calc R . . . .
C13 C 0.2012(2) 0.21419(12) 1.06637(9) 0.0254(3) Uani 1 1 d . . . . .
C14 C 0.0070(2) 0.21304(14) 1.08564(11) 0.0334(3) Uani 1 1 d . . . . .
H14 H -0.071236 0.289692 1.081854 0.040 Uiso 1 1 calc R . . . .
C15 C -0.0709(2) 0.09813(16) 1.11050(12) 0.0391(4) Uani 1 1 d . . . . .
H15 H -0.203766 0.096895 1.122388 0.047 Uiso 1 1 calc R . . . .
C16 C 0.0412(3) -0.01500(14) 1.11835(11) 0.0379(4) Uani 1 1 d . . . . .
C17 C 0.2350(3) -0.01139(14) 1.09736(12) 0.0389(4) Uani 1 1 d . . . . .
H17 H 0.313103 -0.088101 1.101152 0.047 Uiso 1 1 calc R . . . .
C18 C 0.3165(2) 0.10292(14) 1.07086(11) 0.0329(3) Uani 1 1 d . . . . .
H18 H 0.449198 0.104778 1.056033 0.039 Uiso 1 1 calc R . . . .
C19 C -0.0415(2) 0.70108(14) 0.63862(10) 0.0305(3) Uani 1 1 d . . . . .
H19A H 0.028563 0.775670 0.623593 0.046 Uiso 1 1 calc GR . . . .
H19B H -0.117221 0.685204 0.704260 0.046 Uiso 1 1 calc GR . . . .
H19C H -0.124196 0.716999 0.588646 0.046 Uiso 1 1 calc GR . . . .
C20 C -0.0103(2) 0.47007(15) 0.65544(12) 0.0398(4) Uani 1 1 d . . . . .
H20A H -0.099837 0.491305 0.608118 0.060 Uiso 1 1 calc GR . . . .
H20B H -0.078347 0.445223 0.723131 0.060 Uiso 1 1 calc GR . . . .
H20C H 0.079248 0.399192 0.646547 0.060 Uiso 1 1 calc GR . . . .
C21 C 0.4238(2) 0.37595(14) 0.67700(11) 0.0343(3) Uani 1 1 d . . . . .
H21A H 0.560625 0.369928 0.673582 0.052 Uiso 1 1 calc GR . . . .
H21B H 0.389364 0.422222 0.611048 0.052 Uiso 1 1 calc GR . . . .
H21C H 0.381195 0.290049 0.700153 0.052 Uiso 1 1 calc GR . . . .
C22 C -0.0461(4) -0.14021(18) 1.15167(14) 0.0589(6) Uani 1 1 d . . . . .
H22A H -0.081735 -0.168094 1.223811 0.088 Uiso 1 1 calc GR . . . .
H22B H 0.044937 -0.204546 1.132926 0.088 Uiso 1 1 calc GR . . . .
H22C H -0.158041 -0.129233 1.119904 0.088 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 O5 1.4438(12) . ?
S1 O6 1.4378(13) . ?
S1 C12 1.7847(14) . ?
S1 C13 1.7643(15) . ?
O1 C7 1.2042(17) . ?
O2 N1 1.3812(15) . ?
O2 C9 1.4792(16) . ?
O3 C10 1.2079(16) . ?
O4 C11 1.2090(17) . ?
O7 C8 1.2029(18) . ?
N1 C7 1.4021(18) . ?
N1 C8 1.4098(17) . ?
N2 C10 1.4103(17) . ?
N2 C11 1.3960(17) . ?
N2 C21 1.4726(17) . ?
C1 H1 0.9500 . ?
C1 C2 1.399(2) . ?
C1 C6 1.380(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.387(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.393(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.3833(19) . ?
C5 C6 1.3943(19) . ?
C5 C8 1.485(2) . ?
C6 C7 1.4898(18) . ?
C9 C10 1.5541(18) . ?
C9 C19 1.516(2) . ?
C9 C20 1.5203(19) . ?
C11 C12 1.5117(19) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.388(2) . ?
C13 C18 1.387(2) . ?
C14 H14 0.9500 . ?
C14 C15 1.386(2) . ?
C15 H15 0.9500 . ?
C15 C16 1.386(3) . ?
C16 C17 1.388(3) . ?
C16 C22 1.510(2) . ?
C17 H17 0.9500 . ?
C17 C18 1.391(2) . ?
C18 H18 0.9500 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 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
O5 S1 C12 103.97(7) . . ?
O5 S1 C13 108.02(7) . . ?
O6 S1 O5 118.32(7) . . ?
O6 S1 C12 110.13(7) . . ?
O6 S1 C13 108.24(7) . . ?
C13 S1 C12 107.70(6) . . ?
N1 O2 C9 112.51(9) . . ?
O2 N1 C7 121.96(10) . . ?
O2 N1 C8 121.00(11) . . ?
C7 N1 C8 113.64(11) . . ?
C10 N2 C21 122.03(11) . . ?
C11 N2 C10 122.56(11) . . ?
C11 N2 C21 114.83(11) . . ?
C2 C1 H1 121.4 . . ?
C6 C1 H1 121.4 . . ?
C6 C1 C2 117.11(14) . . ?
C1 C2 H2 119.3 . . ?
C3 C2 C1 121.47(14) . . ?
C3 C2 H2 119.3 . . ?
C2 C3 H3 119.5 . . ?
C2 C3 C4 121.10(14) . . ?
C4 C3 H3 119.5 . . ?
C3 C4 H4 121.3 . . ?
C5 C4 C3 117.36(14) . . ?
C5 C4 H4 121.3 . . ?
C4 C5 C6 121.49(14) . . ?
C4 C5 C8 129.47(13) . . ?
C6 C5 C8 109.04(11) . . ?
C1 C6 C5 121.46(13) . . ?
C1 C6 C7 129.97(13) . . ?
C5 C6 C7 108.57(12) . . ?
O1 C7 N1 124.62(13) . . ?
O1 C7 C6 131.25(13) . . ?
N1 C7 C6 104.14(11) . . ?
O7 C8 N1 125.49(13) . . ?
O7 C8 C5 130.69(12) . . ?
N1 C8 C5 103.83(11) . . ?
O2 C9 C10 109.45(11) . . ?
O2 C9 C19 111.17(10) . . ?
O2 C9 C20 103.70(11) . . ?
C19 C9 C10 109.04(11) . . ?
C19 C9 C20 110.46(13) . . ?
C20 C9 C10 112.97(11) . . ?
O3 C10 N2 120.93(12) . . ?
O3 C10 C9 119.94(12) . . ?
N2 C10 C9 118.93(11) . . ?
O4 C11 N2 119.76(13) . . ?
O4 C11 C12 122.64(12) . . ?
N2 C11 C12 117.47(11) . . ?
S1 C12 H12A 108.5 . . ?
S1 C12 H12B 108.5 . . ?
C11 C12 S1 115.21(9) . . ?
C11 C12 H12A 108.5 . . ?
C11 C12 H12B 108.5 . . ?
H12A C12 H12B 107.5 . . ?
C14 C13 S1 118.66(11) . . ?
C18 C13 S1 120.25(12) . . ?
C18 C13 C14 120.95(13) . . ?
C13 C14 H14 120.6 . . ?
C15 C14 C13 118.88(15) . . ?
C15 C14 H14 120.6 . . ?
C14 C15 H15 119.3 . . ?
C16 C15 C14 121.31(16) . . ?
C16 C15 H15 119.3 . . ?
C15 C16 C17 118.82(14) . . ?
C15 C16 C22 120.48(18) . . ?
C17 C16 C22 120.68(17) . . ?
C16 C17 H17 119.5 . . ?
C16 C17 C18 120.94(15) . . ?
C18 C17 H17 119.5 . . ?
C13 C18 C17 119.05(15) . . ?
C13 C18 H18 120.5 . . ?
C17 C18 H18 120.5 . . ?
C9 C19 H19A 109.5 . . ?
C9 C19 H19B 109.5 . . ?
C9 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C9 C20 H20A 109.5 . . ?
C9 C20 H20B 109.5 . . ?
C9 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
N2 C21 H21A 109.5 . . ?
N2 C21 H21B 109.5 . . ?
N2 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C16 C22 H22A 109.5 . . ?
C16 C22 H22B 109.5 . . ?
C16 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
