# 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_xiq003
_database_code_depnum_ccdc_archive 'CCDC 2060106'
loop_
_audit_author_name
_audit_author_address
'Yuqiao Zhou'
;College of Chemistry, Sichuan University, Chengdu, China
China
;
_audit_update_record             
;
2021-02-01 deposited with the CCDC.	2021-06-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H26 N2 O4 S'
_chemical_formula_sum            'C17 H26 N2 O4 S'
_chemical_formula_weight         354.46

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_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. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   9.7300(2)
_cell_length_b                   11.7702(3)
_cell_length_c                   16.4807(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1887.44(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    9915
_cell_measurement_theta_min      5.28
_cell_measurement_theta_max      68.25

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.247
_exptl_crystal_F_000             760
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.319
_exptl_crystal_size_mid          0.295
_exptl_crystal_size_min          0.272
_exptl_absorpt_coefficient_mu    1.712
_shelx_estimated_absorpt_T_min   0.611
_shelx_estimated_absorpt_T_max   0.653
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.6374
_exptl_absorpt_correction_T_max  0.7806
_exptl_absorpt_process_details   'SADABS (Krause et al., 2015)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 Venture Photon II'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            25366
_diffrn_reflns_av_unetI/netI     0.0205
_diffrn_reflns_av_R_equivalents  0.0322
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         5.279
_diffrn_reflns_theta_max         68.307
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             3442
_reflns_number_gt                3401
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.740
_reflns_Friedel_fraction_max     0.993
_reflns_Friedel_fraction_full    0.994

_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. 
;

_computing_data_collection       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0390P)²+0.3899P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
; 
 Flack x determined using 1432 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.043(4)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         3442
_refine_ls_number_parameters     226
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0256
_refine_ls_R_factor_gt           0.0252
_refine_ls_wR_factor_ref         0.0704
_refine_ls_wR_factor_gt          0.0699
_refine_ls_goodness_of_fit_ref   1.101
_refine_ls_restrained_S_all      1.101
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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
S S 0.38852(5) 0.72960(4) 0.39686(3) 0.02551(13) Uani 1 1 d . . . . .
O1 O 0.61952(17) 0.76830(14) 0.23605(8) 0.0324(3) Uani 1 1 d . . . . .
O2 O 0.58527(16) 0.93443(12) 0.29994(8) 0.0278(3) Uani 1 1 d . . . . .
O3 O 0.60112(14) 0.90243(12) 0.49329(8) 0.0247(3) Uani 1 1 d . . . . .
O4 O 0.79193(14) 0.94444(12) 0.42376(8) 0.0223(3) Uani 1 1 d . . . . .
N1 N 0.60538(16) 0.60363(13) 0.43743(9) 0.0188(3) Uani 1 1 d . . . . .
N2 N 0.82177(17) 0.53047(14) 0.46559(10) 0.0192(3) Uani 1 1 d D . . . .
H2N H 0.910(2) 0.546(2) 0.4680(16) 0.032(7) Uiso 1 1 d D . . . .
C1 C 0.74223(18) 0.60719(16) 0.43233(11) 0.0160(4) Uani 1 1 d . . . . .
C2 C 0.80160(18) 0.70881(15) 0.38692(11) 0.0167(4) Uani 1 1 d . . . . .
H2 H 0.867576 0.748548 0.423782 0.020 Uiso 1 1 calc R U . . .
C3 C 0.66937(18) 0.78347(15) 0.37968(10) 0.0160(4) Uani 1 1 d . . . . .
C4 C 0.55312(18) 0.70056(15) 0.40659(11) 0.0175(4) Uani 1 1 d . . . . .
C5 C 0.6255(2) 0.82632(17) 0.29590(11) 0.0203(4) Uani 1 1 d . . . . .
C6 C 0.5187(3) 0.9789(2) 0.22774(15) 0.0447(7) Uani 1 1 d . . . . .
H6A H 0.491369 1.057900 0.237143 0.067 Uiso 1 1 calc R U . . .
H6B H 0.437087 0.933197 0.215456 0.067 Uiso 1 1 calc R U . . .
H6C H 0.582726 0.975437 0.181902 0.067 Uiso 1 1 calc R U . . .
C7 C 0.68064(18) 0.88298(16) 0.43926(11) 0.0166(4) Uani 1 1 d . . . . .
C8 C 0.8143(2) 1.04030(18) 0.47705(14) 0.0293(5) Uani 1 1 d . . . . .
H8A H 0.886024 1.089290 0.454236 0.044 Uiso 1 1 calc R U . . .
H8B H 0.843369 1.012937 0.530535 0.044 Uiso 1 1 calc R U . . .
H8C H 0.728817 1.083607 0.482493 0.044 Uiso 1 1 calc R U . . .
C9 C 0.7776(2) 0.43319(17) 0.51752(13) 0.0229(4) Uani 1 1 d . . . . .
C10 C 0.9090(2) 0.3699(2) 0.54058(18) 0.0394(6) Uani 1 1 d . . . . .
H10A H 0.885738 0.303616 0.573793 0.059 Uiso 1 1 calc R U . . .
H10B H 0.969311 0.420677 0.571512 0.059 Uiso 1 1 calc R U . . .
H10C H 0.956397 0.344949 0.491225 0.059 Uiso 1 1 calc R U . . .
C11 C 0.6837(2) 0.35497(18) 0.46921(15) 0.0290(5) Uani 1 1 d . . . . .
H11A H 0.656655 0.290267 0.503070 0.043 Uiso 1 1 calc R U . . .
H11B H 0.732454 0.327363 0.421067 0.043 Uiso 1 1 calc R U . . .
H11C H 0.601459 0.396899 0.452398 0.043 Uiso 1 1 calc R U . . .
C12 C 0.7067(2) 0.4782(2) 0.59344(13) 0.0327(5) Uani 1 1 d . . . . .
H12A H 0.684497 0.414694 0.629562 0.049 Uiso 1 1 calc R U . . .
H12B H 0.622007 0.517738 0.578063 0.049 Uiso 1 1 calc R U . . .
H12C H 0.768179 0.531204 0.621528 0.049 Uiso 1 1 calc R U . . .
C21 C 0.8775(2) 0.68028(17) 0.30708(12) 0.0237(4) Uani 1 1 d . . . . .
H21 H 0.811176 0.645401 0.268010 0.028 Uiso 1 1 calc R U . . .
C22 C 1.0026(2) 0.6012(2) 0.31673(13) 0.0299(5) Uani 1 1 d . . . . .
H22A H 1.052741 0.617814 0.367653 0.036 Uiso 1 1 calc R U . . .
H22B H 0.973975 0.520510 0.316962 0.036 Uiso 1 1 calc R U . . .
C23 C 1.0916(2) 0.6275(2) 0.24284(14) 0.0397(6) Uani 1 1 d . . . . .
H23A H 1.189625 0.612057 0.254460 0.048 Uiso 1 1 calc R U . . .
H23B H 1.062800 0.581178 0.195661 0.048 Uiso 1 1 calc R U . . .
C24 C 1.0688(3) 0.7515(3) 0.2267(3) 0.0704(11) Uani 1 1 d . . . . .
H24A H 1.147902 0.796009 0.247143 0.084 Uiso 1 1 calc R U . . .
H24B H 1.060478 0.764791 0.167624 0.084 Uiso 1 1 calc R U . . .
C25 C 0.9411(3) 0.7880(2) 0.26837(17) 0.0449(7) Uani 1 1 d . . . . .
H25A H 0.876273 0.822156 0.228999 0.054 Uiso 1 1 calc R U . . .
H25B H 0.962253 0.845060 0.310696 0.054 Uiso 1 1 calc R U . . .


_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
S C4 1.6454(18) . ?
O1 C5 1.201(2) . ?
O2 C5 1.333(2) . ?
O2 C6 1.452(3) . ?
O3 C7 1.202(2) . ?
O4 C7 1.327(2) . ?
O4 C8 1.446(2) . ?
N1 C1 1.335(2) . ?
N1 C4 1.349(2) . ?
N2 C1 1.310(3) . ?
N2 C9 1.493(2) . ?
C1 C2 1.525(2) . ?
C2 C21 1.546(3) . ?
C2 C3 1.563(2) . ?
C3 C5 1.531(2) . ?
C3 C7 1.532(2) . ?
C3 C4 1.558(3) . ?
C9 C11 1.522(3) . ?
C9 C12 1.524(3) . ?
C9 C10 1.528(3) . ?
C21 C22 1.541(3) . ?
C21 C25 1.548(3) . ?
C22 C23 1.526(3) . ?
C23 C24 1.500(4) . ?
C24 C25 1.483(4) . ?

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
C5 O2 C6 115.71(17) . . ?
C7 O4 C8 115.55(15) . . ?
C1 N1 C4 109.02(16) . . ?
C1 N2 C9 126.78(16) . . ?
N2 C1 N1 122.78(17) . . ?
N2 C1 C2 121.50(16) . . ?
N1 C1 C2 115.69(16) . . ?
C1 C2 C21 115.37(15) . . ?
C1 C2 C3 99.60(13) . . ?
C21 C2 C3 116.78(15) . . ?
C5 C3 C7 110.25(15) . . ?
C5 C3 C4 105.11(15) . . ?
C7 C3 C4 110.37(14) . . ?
C5 C3 C2 118.94(15) . . ?
C7 C3 C2 108.78(14) . . ?
C4 C3 C2 102.93(14) . . ?
N1 C4 C3 111.31(15) . . ?
N1 C4 S 125.42(14) . . ?
C3 C4 S 123.27(14) . . ?
O1 C5 O2 124.72(18) . . ?
O1 C5 C3 124.53(18) . . ?
O2 C5 C3 110.58(15) . . ?
O3 C7 O4 124.34(18) . . ?
O3 C7 C3 125.06(17) . . ?
O4 C7 C3 110.59(15) . . ?
N2 C9 C11 109.69(17) . . ?
N2 C9 C12 109.53(17) . . ?
C11 C9 C12 111.62(17) . . ?
N2 C9 C10 105.98(16) . . ?
C11 C9 C10 109.75(18) . . ?
C12 C9 C10 110.12(19) . . ?
C22 C21 C2 114.90(16) . . ?
C22 C21 C25 102.81(18) . . ?
C2 C21 C25 111.33(17) . . ?
C23 C22 C21 104.08(18) . . ?
C24 C23 C22 104.8(2) . . ?
C25 C24 C23 108.9(2) . . ?
C24 C25 C21 106.7(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C9 N2 C1 N1 -4.0(3) . . . . ?
C9 N2 C1 C2 174.24(17) . . . . ?
C4 N1 C1 N2 172.26(17) . . . . ?
C4 N1 C1 C2 -6.1(2) . . . . ?
N2 C1 C2 C21 67.1(2) . . . . ?
N1 C1 C2 C21 -114.51(18) . . . . ?
N2 C1 C2 C3 -167.04(16) . . . . ?
N1 C1 C2 C3 11.4(2) . . . . ?
C1 C2 C3 C5 -126.64(17) . . . . ?
C21 C2 C3 C5 -1.7(2) . . . . ?
C1 C2 C3 C7 106.08(16) . . . . ?
C21 C2 C3 C7 -129.02(16) . . . . ?
C1 C2 C3 C4 -11.01(16) . . . . ?
C21 C2 C3 C4 113.89(17) . . . . ?
C1 N1 C4 C3 -2.4(2) . . . . ?
C1 N1 C4 S 176.97(14) . . . . ?
C5 C3 C4 N1 134.39(16) . . . . ?
C7 C3 C4 N1 -106.75(17) . . . . ?
C2 C3 C4 N1 9.21(19) . . . . ?
C5 C3 C4 S -45.0(2) . . . . ?
C7 C3 C4 S 73.88(19) . . . . ?
C2 C3 C4 S -170.17(13) . . . . ?
C6 O2 C5 O1 5.8(3) . . . . ?
C6 O2 C5 C3 -169.61(19) . . . . ?
C7 C3 C5 O1 173.62(19) . . . . ?
C4 C3 C5 O1 -67.4(2) . . . . ?
C2 C3 C5 O1 47.0(3) . . . . ?
C7 C3 C5 O2 -11.0(2) . . . . ?
C4 C3 C5 O2 107.97(17) . . . . ?
C2 C3 C5 O2 -137.57(17) . . . . ?
C8 O4 C7 O3 -0.1(3) . . . . ?
C8 O4 C7 C3 -179.23(15) . . . . ?
C5 C3 C7 O3 107.2(2) . . . . ?
C4 C3 C7 O3 -8.5(2) . . . . ?
C2 C3 C7 O3 -120.70(19) . . . . ?
C5 C3 C7 O4 -73.64(19) . . . . ?
C4 C3 C7 O4 170.68(14) . . . . ?
C2 C3 C7 O4 58.44(18) . . . . ?
C1 N2 C9 C11 61.6(3) . . . . ?
C1 N2 C9 C12 -61.2(3) . . . . ?
C1 N2 C9 C10 -180.0(2) . . . . ?
C1 C2 C21 C22 -60.3(2) . . . . ?
C3 C2 C21 C22 -176.83(17) . . . . ?
C1 C2 C21 C25 -176.67(18) . . . . ?
C3 C2 C21 C25 66.8(2) . . . . ?
C2 C21 C22 C23 -156.04(19) . . . . ?
C25 C21 C22 C23 -34.9(2) . . . . ?
C21 C22 C23 C24 33.2(3) . . . . ?
C22 C23 C24 C25 -18.4(4) . . . . ?
C23 C24 C25 C21 -3.8(4) . . . . ?
C22 C21 C25 C24 24.0(3) . . . . ?
C2 C21 C25 C24 147.5(3) . . . . ?

_refine_diff_density_max         0.248
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.035


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: EtOAc, PE'
####################################################################### 
# 
# 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_xiq005
_database_code_depnum_ccdc_archive 'CCDC 1997917'
loop_
_audit_author_name
_audit_author_address
'Yuqiao Zhou'
;College of Chemistry, Sichuan University, Chengdu, China
China
;
_audit_update_record             
;
2021-04-15 deposited with the CCDC.	2021-06-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H22 N2 O4 S'
_chemical_formula_sum            'C18 H22 N2 O4 S'
_chemical_formula_weight         362.43

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           18
_space_group_name_H-M_alt        'P 21 21 2'
_space_group_name_Hall           'P 2 2ab'

_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. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'-x+1/2, y+1/2, -z'
'x+1/2, -y+1/2, -z'

_cell_length_a                   12.4981(5)
_cell_length_b                   17.3226(8)
_cell_length_c                   8.4593(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1831.44(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    9992
_cell_measurement_theta_min      2.68
_cell_measurement_theta_max      25.34

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.314
_exptl_crystal_F_000             768
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.763
_exptl_crystal_size_mid          0.545
_exptl_crystal_size_min          0.284
_exptl_absorpt_coefficient_mu    0.201
_shelx_estimated_absorpt_T_min   0.862
_shelx_estimated_absorpt_T_max   0.945
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.8978
_exptl_absorpt_correction_T_max  0.9895
_exptl_absorpt_process_details   'SADABS (Krause et al., 2015)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 Venture Photon II'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            43777
_diffrn_reflns_av_unetI/netI     0.0248
_diffrn_reflns_av_R_equivalents  0.0522
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.680
_diffrn_reflns_theta_max         25.430
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             3366
_reflns_number_gt                3139
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.737
_reflns_Friedel_fraction_max     0.997
_reflns_Friedel_fraction_full    0.997

_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. 
;

_computing_data_collection       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0343P)²+0.3686P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
; 
 Flack x determined using 1264 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.002(14)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         3366
_refine_ls_number_parameters     235
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0366
_refine_ls_R_factor_gt           0.0308
_refine_ls_wR_factor_ref         0.0678
_refine_ls_wR_factor_gt          0.0664
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_restrained_S_all      1.066
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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
S S 0.59917(4) 0.72702(4) 0.23863(8) 0.03742(17) Uani 1 1 d . . . . .
O1 O 0.39409(15) 0.60628(10) 0.17072(19) 0.0369(4) Uani 1 1 d . . . . .
O2 O 0.37741(12) 0.55950(8) 0.41642(19) 0.0278(4) Uani 1 1 d . . . . .
O3 O 0.53757(11) 0.65854(9) 0.5830(2) 0.0313(4) Uani 1 1 d . . . . .
O4 O 0.38167(12) 0.70463(10) 0.66917(18) 0.0351(4) Uani 1 1 d . . . . .
N1 N 0.42089(12) 0.81122(10) 0.2385(2) 0.0258(4) Uani 1 1 d . . . . .
N2 N 0.24662(13) 0.85956(9) 0.2605(2) 0.0236(4) Uani 1 1 d D . . . .
H2N H 0.1860(16) 0.8497(12) 0.300(3) 0.025(6) Uiso 1 1 d D . . . .
C1 C 0.32030(15) 0.80675(11) 0.2887(2) 0.0207(4) Uani 1 1 d . . . . .
C2 C 0.29332(15) 0.73694(11) 0.3873(2) 0.0200(4) Uani 1 1 d . . . . .
H2 H 0.277440 0.755091 0.497003 0.024 Uiso 1 1 calc R U . . .
C3 C 0.40380(15) 0.69423(12) 0.3908(2) 0.0211(4) Uani 1 1 d . . . . .
C4 C 0.47486(16) 0.74740(12) 0.2869(3) 0.0248(5) Uani 1 1 d . . . . .
C5 C 0.39340(16) 0.61540(13) 0.3107(3) 0.0242(5) Uani 1 1 d . . . . .
C6 C 0.3531(2) 0.48414(13) 0.3517(3) 0.0378(6) Uani 1 1 d . . . . .
H6A H 0.365869 0.444567 0.432348 0.057 Uiso 1 1 calc R U . . .
H6B H 0.398956 0.474273 0.260014 0.057 Uiso 1 1 calc R U . . .
H6C H 0.277855 0.482555 0.319085 0.057 Uiso 1 1 calc R U . . .
C7 C 0.44994(16) 0.68370(12) 0.5570(3) 0.0225(4) Uani 1 1 d . . . . .
C8 C 0.4148(2) 0.69269(17) 0.8315(3) 0.0423(6) Uani 1 1 d . . . . .
H8A H 0.358932 0.711670 0.902947 0.063 Uiso 1 1 calc R U . . .
H8B H 0.481446 0.720846 0.851252 0.063 Uiso 1 1 calc R U . . .
H8C H 0.426301 0.637470 0.850078 0.063 Uiso 1 1 calc R U . . .
C9 C 0.25870(17) 0.93168(12) 0.1665(3) 0.0265(5) Uani 1 1 d . . . . .
C10 C 0.2944(2) 0.91213(16) 0.0010(3) 0.0406(6) Uani 1 1 d . . . . .
H10A H 0.240733 0.879112 -0.049505 0.061 Uiso 1 1 calc R U . . .
H10B H 0.363031 0.884816 0.005309 0.061 Uiso 1 1 calc R U . . .
H10C H 0.302739 0.959772 -0.060225 0.061 Uiso 1 1 calc R U . . .
C11 C 0.1488(2) 0.96917(16) 0.1598(4) 0.0475(7) Uani 1 1 d . . . . .
H11A H 0.098068 0.933791 0.109171 0.071 Uiso 1 1 calc R U . . .
H11B H 0.152937 1.017104 0.098620 0.071 Uiso 1 1 calc R U . . .
H11C H 0.124409 0.980760 0.267361 0.071 Uiso 1 1 calc R U . . .
C12 C 0.3387(2) 0.98440(14) 0.2481(4) 0.0527(7) Uani 1 1 d . . . . .
H12A H 0.315329 0.994164 0.356864 0.079 Uiso 1 1 calc R U . . .
H12B H 0.343256 1.033420 0.190657 0.079 Uiso 1 1 calc R U . . .
H12C H 0.409215 0.959618 0.249420 0.079 Uiso 1 1 calc R U . . .
C21 C 0.19861(15) 0.68939(11) 0.3312(3) 0.0232(5) Uani 1 1 d . . . . .
C22 C 0.16862(18) 0.68565(13) 0.1736(3) 0.0317(5) Uani 1 1 d . . . . .
H22 H 0.207292 0.714045 0.096370 0.038 Uiso 1 1 calc R U . . .
C23 C 0.0820(2) 0.64041(14) 0.1286(4) 0.0460(7) Uani 1 1 d . . . . .
H23 H 0.061399 0.637836 0.020642 0.055 Uiso 1 1 calc R U . . .
C24 C 0.0262(2) 0.59927(15) 0.2410(4) 0.0567(9) Uani 1 1 d . . . . .
H24 H -0.033302 0.568585 0.210227 0.068 Uiso 1 1 calc R U . . .
C25 C 0.0558(2) 0.60234(16) 0.3970(4) 0.0517(8) Uani 1 1 d . . . . .
H25 H 0.017199 0.573490 0.473596 0.062 Uiso 1 1 calc R U . . .
C26 C 0.14186(18) 0.64735(13) 0.4432(3) 0.0336(6) Uani 1 1 d . . . . .
H26 H 0.162079 0.649492 0.551405 0.040 Uiso 1 1 calc R U . . .


_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
S C4 1.645(2) . ?
O1 C5 1.195(3) . ?
O2 C5 1.333(3) . ?
O2 C6 1.448(3) . ?
O3 C7 1.199(2) . ?
O4 C7 1.327(3) . ?
O4 C8 1.449(3) . ?
N1 C1 1.329(3) . ?
N1 C4 1.358(3) . ?
N2 C1 1.320(3) . ?
N2 C9 1.488(3) . ?
C1 C2 1.507(3) . ?
C2 C21 1.518(3) . ?
C2 C3 1.567(3) . ?
C3 C5 1.530(3) . ?
C3 C7 1.531(3) . ?
C3 C4 1.552(3) . ?
C9 C10 1.508(4) . ?
C9 C12 1.520(3) . ?
C9 C11 1.521(3) . ?
C21 C22 1.386(3) . ?
C21 C26 1.390(3) . ?
C22 C23 1.389(3) . ?
C23 C24 1.378(4) . ?
C24 C25 1.372(5) . ?
C25 C26 1.385(3) . ?

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
C5 O2 C6 115.66(18) . . ?
C7 O4 C8 117.08(17) . . ?
C1 N1 C4 109.02(17) . . ?
C1 N2 C9 127.40(17) . . ?
N2 C1 N1 124.19(19) . . ?
N2 C1 C2 119.99(17) . . ?
N1 C1 C2 115.79(17) . . ?
C1 C2 C21 115.90(17) . . ?
C1 C2 C3 101.08(15) . . ?
C21 C2 C3 115.91(16) . . ?
C5 C3 C7 109.42(16) . . ?
C5 C3 C4 109.12(17) . . ?
C7 C3 C4 112.04(16) . . ?
C5 C3 C2 109.76(16) . . ?
C7 C3 C2 113.93(16) . . ?
C4 C3 C2 102.31(15) . . ?
N1 C4 C3 111.69(16) . . ?
N1 C4 S 124.67(16) . . ?
C3 C4 S 123.62(15) . . ?
O1 C5 O2 124.7(2) . . ?
O1 C5 C3 123.8(2) . . ?
O2 C5 C3 111.35(17) . . ?
O3 C7 O4 123.8(2) . . ?
O3 C7 C3 123.8(2) . . ?
O4 C7 C3 112.47(16) . . ?
N2 C9 C10 109.72(18) . . ?
N2 C9 C12 109.18(19) . . ?
C10 C9 C12 111.2(2) . . ?
N2 C9 C11 106.66(17) . . ?
C10 C9 C11 109.2(2) . . ?
C12 C9 C11 110.8(2) . . ?
C22 C21 C26 119.6(2) . . ?
C22 C21 C2 122.45(19) . . ?
C26 C21 C2 118.0(2) . . ?
C21 C22 C23 120.0(2) . . ?
C24 C23 C22 119.8(3) . . ?
C25 C24 C23 120.4(2) . . ?
C24 C25 C26 120.2(3) . . ?
C25 C26 C21 119.9(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C9 N2 C1 N1 1.8(4) . . . . ?
C9 N2 C1 C2 180.0(2) . . . . ?
C4 N1 C1 N2 -179.6(2) . . . . ?
C4 N1 C1 C2 2.1(3) . . . . ?
N2 C1 C2 C21 55.4(3) . . . . ?
N1 C1 C2 C21 -126.3(2) . . . . ?
N2 C1 C2 C3 -178.47(18) . . . . ?
N1 C1 C2 C3 -0.1(2) . . . . ?
C1 C2 C3 C5 -117.40(17) . . . . ?
C21 C2 C3 C5 8.8(2) . . . . ?
C1 C2 C3 C7 119.51(18) . . . . ?
C21 C2 C3 C7 -114.3(2) . . . . ?
C1 C2 C3 C4 -1.64(19) . . . . ?
C21 C2 C3 C4 124.52(18) . . . . ?
C1 N1 C4 C3 -3.3(2) . . . . ?
C1 N1 C4 S 175.24(17) . . . . ?
C5 C3 C4 N1 119.29(19) . . . . ?
C7 C3 C4 N1 -119.38(19) . . . . ?
C2 C3 C4 N1 3.1(2) . . . . ?
C5 C3 C4 S -59.2(2) . . . . ?
C7 C3 C4 S 62.1(2) . . . . ?
C2 C3 C4 S -175.46(15) . . . . ?
C6 O2 C5 O1 -3.9(3) . . . . ?
C6 O2 C5 C3 172.51(18) . . . . ?
C7 C3 C5 O1 -154.5(2) . . . . ?
C4 C3 C5 O1 -31.5(3) . . . . ?
C2 C3 C5 O1 79.8(3) . . . . ?
C7 C3 C5 O2 29.1(2) . . . . ?
C4 C3 C5 O2 152.04(16) . . . . ?
C2 C3 C5 O2 -96.58(19) . . . . ?
C8 O4 C7 O3 -2.8(3) . . . . ?
C8 O4 C7 C3 176.4(2) . . . . ?
C5 C3 C7 O3 63.5(3) . . . . ?
C4 C3 C7 O3 -57.7(3) . . . . ?
C2 C3 C7 O3 -173.26(19) . . . . ?
C5 C3 C7 O4 -115.77(19) . . . . ?
C4 C3 C7 O4 123.07(19) . . . . ?
C2 C3 C7 O4 7.5(2) . . . . ?
C1 N2 C9 C10 57.7(3) . . . . ?
C1 N2 C9 C12 -64.4(3) . . . . ?
C1 N2 C9 C11 175.8(2) . . . . ?
C1 C2 C21 C22 28.3(3) . . . . ?
C3 C2 C21 C22 -90.0(2) . . . . ?
C1 C2 C21 C26 -152.87(18) . . . . ?
C3 C2 C21 C26 88.9(2) . . . . ?
C26 C21 C22 C23 0.3(3) . . . . ?
C2 C21 C22 C23 179.2(2) . . . . ?
C21 C22 C23 C24 0.0(4) . . . . ?
C22 C23 C24 C25 -0.4(4) . . . . ?
C23 C24 C25 C26 0.5(5) . . . . ?
C24 C25 C26 C21 -0.2(4) . . . . ?
C22 C21 C26 C25 -0.2(3) . . . . ?
C2 C21 C26 C25 -179.1(2) . . . . ?

_refine_diff_density_max         0.179
_refine_diff_density_min         -0.201
_refine_diff_density_rms         0.036


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: EAC, PE'
