# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2022

####################################################################### 
# 
# 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_mo_aks_08022021_vs_7_81_1_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2120261'
loop_
_audit_author_name
_audit_author_address
'Rangu Prasad'
;University of Hyderabad
India
;
_audit_update_record             
;
2021-11-04 deposited with the CCDC.	2022-06-20 downloaded from the CCDC.
;
_audit_creation_date             2021-02-14
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2019.04.23 svn.r3594 for Rigaku Oxford Diffraction, GUI svn.r5739)
;
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C24 H21 N O4 S'
_chemical_formula_sum            'C24 H21 N O4 S'
_chemical_formula_weight         419.50
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
S 0.12424 0.12443 6.90530 5.20340 1.43790 1.58630 1.46790 22.21510 0.25360
56.17200 0.866900026798
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x+1/2,y+1/2,-z+1/2
3 -x,-y,-z
4 x-1/2,-y-1/2,z-1/2

_symmetry_Int_Tables_number      14
_cell_length_a                   8.2335(3)
_cell_length_b                   18.3922(8)
_cell_length_c                   14.6378(6)
_cell_angle_alpha                90
_cell_angle_beta                 104.229(1)
_cell_angle_gamma                90
_cell_volume                     2148.63(15)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8812
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.42
_cell_measurement_theta_min      2.21
_exptl_absorpt_coefficient_mu    0.181
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6890
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1169 before and 0.0546 after correction.
The Ratio of minimum to maximum transmission is 0.9240.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.2967
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       TRIANGULAR
_exptl_crystal_F_000             880.9287
_exptl_crystal_size_max          0.198
_exptl_crystal_size_mid          0.168
_exptl_crystal_size_min          0.068
_diffrn_reflns_av_R_equivalents  0.0494
_diffrn_reflns_av_unetI/netI     0.0307
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            44337
_diffrn_reflns_theta_full        28.2978
_diffrn_reflns_theta_max         28.30
_diffrn_reflns_theta_min         2.21
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.9983
_diffrn_measured_fraction_theta_max 0.9981
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              8
_reflns_limit_h_min              -10
_reflns_limit_k_max              24
_reflns_limit_k_min              0
_reflns_limit_l_max              19
_reflns_limit_l_min              -7
_reflns_number_gt                3710
_reflns_number_total             5318
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'SAINT V8.40A (?, 2016)'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.3261
_refine_diff_density_min         -0.4031
_refine_diff_density_rms         0.0548
_refine_ls_d_res_high            0.7496
_refine_ls_d_res_low             9.1961
_refine_ls_goodness_of_fit_ref   1.0557
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    37
_refine_ls_number_parameters     272
_refine_ls_number_reflns         5318
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0744
_refine_ls_R_factor_gt           0.0476
_refine_ls_restrained_S_all      1.0557
_refine_ls_shift/su_max          0.0182
_refine_ls_shift/su_mean         0.0004
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0591P)²+0.5719P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1226
_refine_ls_wR_factor_ref         0.1404
_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 fixed occupancy and ADP/Uiso:
 C21J(H21J)
2.b Secondary CH2 refined with riding coordinates:
 C15B(H15a,H15b), C23N(H23a,H23b), C22R(H22a,H22b)
2.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C6A(H6A), C3E(H3E), C7K(H7K), C17L(H17L), C10O(H10O), C12P(H12P),
 C8Q(H8Q), C24S(H24S), C9T(H9T)
2.d Idealised Me refined as rotating group:
 C1U(H1Ua,H1Ub,H1Uc)
2.e :
 C20(H20)
;
_atom_sites_solution_primary     iterative
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_refinement_flags_posn
S1 S 0.49628(6) 0.62166(3) 0.94148(3) 0.05486(16) Uani 1.000000 .
O2 O 0.12433(16) 0.54436(8) 0.84754(10) 0.0569(3) Uani 1.000000 .
O3 O 0.3615(2) 0.66065(9) 0.96391(11) 0.0753(5) Uani 1.000000 .
N1 N 0.40855(18) 0.56734(8) 0.85442(10) 0.0460(3) Uani 1.000000 .
O4 O 0.6061(2) 0.57901(10) 1.01149(10) 0.0815(5) Uani 1.000000 .
O1 O 0.1242(3) 0.44214(10) 0.76399(14) 0.0980(7) Uani 1.000000 .
C5 C 0.6209(2) 0.68244(10) 0.89629(12) 0.0471(4) Uani 1.000000 .
C16 C 0.2416(2) 0.57810(10) 0.80410(13) 0.0487(4) Uani 1.000000 .
C4 C 0.5546(3) 0.74680(11) 0.85535(14) 0.0552(5) Uani 1.000000 .
H4 H 0.4444(3) 0.75927(11) 0.85355(14) 0.0662(6) Uiso 1.000000 R
C6A C 0.7844(2) 0.66407(11) 0.89903(15) 0.0583(5) Uani 1.000000 .
H6A H 0.8293(2) 0.62068(11) 0.92680(15) 0.0699(6) Uiso 1.000000 R
C15B C 0.5077(3) 0.50797(11) 0.82795(15) 0.0561(5) Uani 1.000000 .
H15a H 0.5969(3) 0.49493(11) 0.88223(15) 0.0673(6) Uiso 1.000000 R
H15b H 0.4364(3) 0.46570(11) 0.81049(15) 0.0673(6) Uiso 1.000000 R
C14 C 0.5811(2) 0.52695(11) 0.74971(15) 0.0545(5) Uani 1.000000 .
C13D C 0.6356(3) 0.54330(11) 0.68482(15) 0.0566(5) Uani 1.000000 .
C3E C 0.6530(3) 0.79258(11) 0.81705(15) 0.0600(5) Uani 1.000000 .
H3E H 0.6083(3) 0.83622(11) 0.78995(15) 0.0720(6) Uiso 1.000000 R
C2F C 0.8166(3) 0.77487(11) 0.81816(14) 0.0568(5) Uani 1.000000 .
C18G C 0.0806(3) 0.47539(12) 0.82375(15) 0.0600(5) Uani 1.000000 .
C11H C 0.6946(2) 0.56549(11) 0.60456(14) 0.0544(5) Uani 1.000000 .
C19I C -0.0263(3) 0.44619(12) 0.87921(15) 0.0603(5) Uani 1.000000 .
C21J C 0.2885(3) 0.65898(11) 0.67818(14) 0.0597(5) Uani 1.000000 .
H21J H 0.4094(3) 0.65772(11) 0.70656(14) 0.0716(6) Uiso 1.000000 .
C7K C 0.8812(3) 0.71067(12) 0.86015(16) 0.0624(5) Uani 1.000000 .
H7K H 0.9917(3) 0.69839(12) 0.86245(16) 0.0749(6) Uiso 1.000000 R
C17L C 0.1866(3) 0.61654(12) 0.72686(15) 0.0593(5) Uani 1.000000 .
H17L H 0.0716(3) 0.61657(12) 0.70092(15) 0.0711(6) Uiso 1.000000 R
C20 C -0.1067(3) 0.41845(14) 0.92545(16) 0.0718(6) Uani 1.000000 .
H20 H -0.1705(3) 0.39647(14) 0.96209(16) 0.0862(8) Uiso 1.000000 R
C23N C 0.2389(3) 0.66624(15) 0.57230(17) 0.0780(7) Uani 1.000000 .
H23a H 0.3278(3) 0.66711(15) 0.53939(17) 0.0936(8) Uiso 1.000000 R
H23b H 0.1368(3) 0.64231(15) 0.53855(17) 0.0936(8) Uiso 1.000000 R
C10O C 0.7147(3) 0.63819(13) 0.58680(16) 0.0680(6) Uani 1.000000 .
H10O H 0.6940(3) 0.67328(13) 0.62826(16) 0.0817(7) Uiso 1.000000 R
C12P C 0.7287(3) 0.51434(14) 0.54220(17) 0.0754(7) Uani 1.000000 .
H12P H 0.7166(3) 0.46510(14) 0.55338(17) 0.0905(8) Uiso 1.000000 R
C8Q C 0.7983(3) 0.60753(16) 0.44648(17) 0.0785(7) Uani 1.000000 .
H8Q H 0.8329(3) 0.62170(16) 0.39324(17) 0.0942(8) Uiso 1.000000 R
C22R C 0.2229(4) 0.72931(14) 0.63111(18) 0.0834(8) Uani 1.000000 .
H22a H 0.1109(4) 0.74414(14) 0.63332(18) 0.1001(9) Uiso 1.000000 R
H22b H 0.3019(4) 0.76892(14) 0.63415(18) 0.1001(9) Uiso 1.000000 R
C24S C 0.7804(4) 0.53606(16) 0.46374(18) 0.0831(7) Uani 1.000000 .
H24S H 0.8031(4) 0.50135(16) 0.42235(18) 0.0997(9) Uiso 1.000000 R
C9T C 0.7659(3) 0.65895(15) 0.50710(18) 0.0800(7) Uani 1.000000 .
H9T H 0.7781(3) 0.70800(15) 0.49488(18) 0.0960(8) Uiso 1.000000 R
C1U C 0.9221(3) 0.82453(15) 0.7745(2) 0.0894(8) Uani 1.000000 .
H1Ua H 1.0313(9) 0.8036(6) 0.7815(13) 0.1341(12) Uiso 1.000000 GR
H1Ub H 0.8697(14) 0.8307(9) 0.7087(4) 0.1341(12) Uiso 1.000000 GR
H1Uc H 0.933(2) 0.8710(4) 0.8053(10) 0.1341(12) Uiso 1.000000 GR


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 1.4256(16) . ?
S1 N1 1.6406(16) . ?
S1 O4 1.4238(16) . ?
S1 C5 1.7534(18) . ?
O2 C16 1.423(2) . ?
O2 C18G 1.341(2) . ?
N1 C16 1.405(2) . ?
N1 C15B 1.471(2) . ?
O1 C18G 1.193(3) . ?
C5 C4 1.378(3) . ?
C5 C6A 1.378(3) . ?
C16 C17L 1.316(3) . ?
C4 H4 0.9300 . ?
C4 C3E 1.379(3) . ?
C6A H6A 0.9300 . ?
C6A C7K 1.385(3) . ?
C15B H15a 0.9700 . ?
C15B H15b 0.9700 . ?
C15B C14 1.463(3) . ?
C14 C13D 1.185(3) . ?
C13D C11H 1.436(3) . ?
C3E H3E 0.9300 . ?
C3E C2F 1.382(3) . ?
C2F C7K 1.376(3) . ?
C2F C1U 1.507(3) . ?
C18G C19I 1.440(3) . ?
C11H C10O 1.380(3) . ?
C11H C12P 1.387(3) . ?
C19I C20 1.174(3) . ?
C21J H21J 0.9800 . ?
C21J C17L 1.454(3) . ?
C21J C23N 1.508(3) . ?
C21J C22R 1.502(3) . ?
C7K H7K 0.9300 . ?
C17L H17L 0.9300 . ?
C20 H20 0.9300 . ?
C23N H23a 0.9700 . ?
C23N H23b 0.9700 . ?
C23N C22R 1.470(4) . ?
C10O H10O 0.9300 . ?
C10O C9T 1.388(3) . ?
C12P H12P 0.9300 . ?
C12P C24S 1.378(3) . ?
C8Q H8Q 0.9300 . ?
C8Q C24S 1.353(4) . ?
C8Q C9T 1.368(4) . ?
C22R H22a 0.9700 . ?
C22R H22b 0.9700 . ?
C24S H24S 0.9300 . ?
C9T H9T 0.9300 . ?
C1U H1Ua 0.9600 . ?
C1U H1Ub 0.9600 . ?
C1U H1Uc 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
N1 S1 O3 105.44(9) . . ?
O4 S1 O3 120.24(11) . . ?
O4 S1 N1 107.69(10) . . ?
C5 S1 O3 109.10(10) . . ?
C5 S1 N1 106.38(8) . . ?
C5 S1 O4 107.21(9) . . ?
C18G O2 C16 117.71(15) . . ?
C16 N1 S1 120.58(12) . . ?
C15B N1 S1 119.33(13) . . ?
C15B N1 C16 120.08(16) . . ?
C4 C5 S1 120.37(14) . . ?
C6A C5 S1 119.38(15) . . ?
C6A C5 C4 120.21(17) . . ?
N1 C16 O2 112.85(15) . . ?
C17L C16 O2 119.37(17) . . ?
C17L C16 N1 127.73(17) . . ?
H4 C4 C5 120.28(11) . . ?
C3E C4 C5 119.44(18) . . ?
C3E C4 H4 120.28(12) . . ?
H6A C6A C5 120.23(11) . . ?
C7K C6A C5 119.54(18) . . ?
C7K C6A H6A 120.23(12) . . ?
H15a C15B N1 108.97(10) . . ?
H15b C15B N1 108.97(10) . . ?
H15b C15B H15a 107.8 . . ?
C14 C15B N1 113.07(15) . . ?
C14 C15B H15a 108.97(12) . . ?
C14 C15B H15b 108.97(12) . . ?
C13D C14 C15B 177.8(2) . . ?
C11H C13D C14 177.1(2) . . ?
H3E C3E C4 119.35(12) . . ?
C2F C3E C4 121.29(19) . . ?
C2F C3E H3E 119.35(12) . . ?
C7K C2F C3E 118.44(18) . . ?
C1U C2F C3E 120.9(2) . . ?
C1U C2F C7K 120.6(2) . . ?
O1 C18G O2 124.43(18) . . ?
C19I C18G O2 111.64(18) . . ?
C19I C18G O1 123.9(2) . . ?
C10O C11H C13D 120.65(19) . . ?
C12P C11H C13D 120.6(2) . . ?
C12P C11H C10O 118.70(19) . . ?
C20 C19I C18G 175.6(3) . . ?
C17L C21J H21J 115.33(12) . . ?
C23N C21J H21J 115.33(14) . . ?
C23N C21J C17L 120.5(2) . . ?
C22R C21J H21J 115.33(15) . . ?
C22R C21J C17L 120.1(2) . . ?
C22R C21J C23N 58.43(16) . . ?
C2F C7K C6A 121.06(19) . . ?
H7K C7K C6A 119.47(12) . . ?
H7K C7K C2F 119.47(12) . . ?
C21J C17L C16 126.25(19) . . ?
H17L C17L C16 116.87(12) . . ?
H17L C17L C21J 116.87(12) . . ?
H20 C20 C19I 180.0 . . ?
H23a C23N C21J 117.71(14) . . ?
H23b C23N C21J 117.71(14) . . ?
H23b C23N H23a 114.8 . . ?
C22R C23N C21J 60.57(16) . . ?
C22R C23N H23a 117.71(16) . . ?
C22R C23N H23b 117.71(16) . . ?
H10O C10O C11H 119.99(12) . . ?
C9T C10O C11H 120.0(2) . . ?
C9T C10O H10O 119.99(16) . . ?
H12P C12P C11H 119.81(13) . . ?
C24S C12P C11H 120.4(2) . . ?
C24S C12P H12P 119.81(16) . . ?
C24S C8Q H8Q 119.91(15) . . ?
C9T C8Q H8Q 119.91(15) . . ?
C9T C8Q C24S 120.2(2) . . ?
C23N C22R C21J 60.99(15) . . ?
H22a C22R C21J 117.67(14) . . ?
H22a C22R C23N 117.67(16) . . ?
H22b C22R C21J 117.67(15) . . ?
H22b C22R C23N 117.67(16) . . ?
H22b C22R H22a 114.8 . . ?
C8Q C24S C12P 120.5(2) . . ?
H24S C24S C12P 119.76(16) . . ?
H24S C24S C8Q 119.76(15) . . ?
C8Q C9T C10O 120.2(2) . . ?
H9T C9T C10O 119.89(16) . . ?
H9T C9T C8Q 119.89(15) . . ?
H1Ua C1U C2F 109.5 . . ?
H1Ub C1U C2F 109.5 . . ?
H1Ub C1U H1Ua 109.5 . . ?
H1Uc C1U C2F 109.5 . . ?
H1Uc C1U H1Ua 109.5 . . ?
H1Uc C1U H1Ub 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 
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data_mo_AKS_18022021_VS_7_82_4_1_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2120262'
loop_
_audit_author_name
_audit_author_address
'Rangu Prasad'
;University of Hyderabad
India
;
_audit_update_record             
;
2021-11-04 deposited with the CCDC.	2022-06-20 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         ?
_chemical_formula_sum            'C27 H23 N O4 S'
_chemical_formula_weight         457.52

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           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                   8.793(3)
_cell_length_b                   15.899(5)
_cell_length_c                   17.594(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2459.6(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    196
_cell_measurement_theta_min      2.56
_cell_measurement_theta_max      10.90

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.236
_exptl_crystal_F_000             960
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.223
_exptl_crystal_size_mid          0.166
_exptl_crystal_size_min          0.075
_exptl_absorpt_coefficient_mu    0.164
_shelx_estimated_absorpt_T_min   0.964
_shelx_estimated_absorpt_T_max   0.988
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6806
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'micro-focus sealed tube'
_diffrn_measurement_device_type  'Bruker D8 VENTURE Photon III detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            26882
_diffrn_reflns_av_unetI/netI     0.0551
_diffrn_reflns_av_R_equivalents  0.0618
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.315
_diffrn_reflns_theta_max         28.304
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             6113
_reflns_number_gt                3288
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.773
_reflns_Friedel_fraction_max     0.996
_reflns_Friedel_fraction_full    0.999

_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 SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_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)+(0.0616P)²+0.0227P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1059 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.00(4)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         6113
_refine_ls_number_parameters     299
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1062
_refine_ls_R_factor_gt           0.0462
_refine_ls_wR_factor_ref         0.1349
_refine_ls_wR_factor_gt          0.1094
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_restrained_S_all      1.007
_refine_ls_shift/su_max          0.022
_refine_ls_shift/su_mean         0.002

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 0.36997(11) 0.79627(6) 0.26586(5) 0.0706(3) Uani 1 1 d . . . . .
O1 O 0.5482(3) 0.63833(15) 0.30160(12) 0.0718(7) Uani 1 1 d . . . . .
O5 O 0.2616(3) 0.72954(19) 0.26661(16) 0.0932(8) Uani 1 1 d . . . . .
O2 O 0.3389(4) 0.87291(17) 0.22695(15) 0.0942(9) Uani 1 1 d . . . . .
O3 O 0.3891(4) 0.52959(16) 0.27196(16) 0.0920(9) Uani 1 1 d . . . . .
N N 0.5225(3) 0.75699(16) 0.22652(15) 0.0610(7) Uani 1 1 d . . . . .
C21 C 0.5851(4) 0.6231(2) 0.16822(19) 0.0694(10) Uani 1 1 d . . . . .
H21 H 0.614859 0.568362 0.179501 0.083 Uiso 1 1 calc R U . . .
C6 C 0.4123(4) 0.8224(2) 0.36062(18) 0.0648(9) Uani 1 1 d . . . . .
C22 C 0.5862(4) 0.6457(2) 0.08723(19) 0.0683(9) Uani 1 1 d . . . . .
C11 C 0.4592(5) 0.5690(2) 0.3171(2) 0.0737(10) Uani 1 1 d . . . . .
C10 C 0.5478(4) 0.6699(2) 0.22670(18) 0.0631(8) Uani 1 1 d . . . . .
C14 C 0.4559(5) 0.5111(2) 0.5415(2) 0.0695(9) Uani 1 1 d . . . . .
C13 C 0.4609(5) 0.5342(2) 0.4632(2) 0.0750(10) Uani 1 1 d . . . . .
C12 C 0.4640(5) 0.5525(2) 0.3977(2) 0.0799(11) Uani 1 1 d . . . . .
C5 C 0.4930(5) 0.8940(2) 0.3764(2) 0.0788(11) Uani 1 1 d . . . . .
H5 H 0.529993 0.927174 0.336927 0.095 Uiso 1 1 calc R U . . .
C19 C 0.3733(5) 0.4417(2) 0.5641(2) 0.0817(11) Uani 1 1 d . . . . .
H19 H 0.318608 0.410926 0.528419 0.098 Uiso 1 1 calc R U . . .
C20 C 0.4878(5) 0.7028(3) 0.05553(19) 0.0793(11) Uani 1 1 d . . . . .
H20 H 0.417959 0.730530 0.086266 0.095 Uiso 1 1 calc R U . . .
C15 C 0.5363(5) 0.5567(3) 0.5952(2) 0.0874(12) Uani 1 1 d . . . . .
H15 H 0.591093 0.604147 0.580853 0.105 Uiso 1 1 calc R U . . .
C23 C 0.4913(6) 0.7195(3) -0.0218(2) 0.0992(14) Uani 1 1 d . . . . .
H23 H 0.425207 0.758959 -0.042496 0.119 Uiso 1 1 calc R U . . .
C4 C 0.5191(5) 0.9168(3) 0.4509(2) 0.0931(13) Uani 1 1 d . . . . .
H4 H 0.575138 0.965169 0.460938 0.112 Uiso 1 1 calc R U . . .
C16 C 0.5344(6) 0.5313(3) 0.6699(3) 0.1036(15) Uani 1 1 d . . . . .
H16 H 0.588914 0.561210 0.706321 0.124 Uiso 1 1 calc R U . . .
C7 C 0.3576(5) 0.7732(2) 0.4195(2) 0.0855(12) Uani 1 1 d . . . . .
H7 H 0.303622 0.724172 0.409548 0.103 Uiso 1 1 calc R U . . .
C26 C 0.6849(5) 0.6053(3) 0.0389(2) 0.0882(12) Uani 1 1 d . . . . .
H26 H 0.751956 0.565684 0.058719 0.106 Uiso 1 1 calc R U . . .
C1 C 0.6472(5) 0.8126(2) 0.2009(2) 0.0834(11) Uani 1 1 d . . . . .
H1A H 0.676573 0.797196 0.149582 0.100 Uiso 1 1 calc R U . . .
H1B H 0.611328 0.870304 0.199817 0.100 Uiso 1 1 calc R U . . .
C3 C 0.4650(6) 0.8703(3) 0.5102(2) 0.0926(13) Uani 1 1 d . . . . .
C18 C 0.3718(6) 0.4181(3) 0.6393(3) 0.1008(14) Uani 1 1 d . . . . .
H18 H 0.315052 0.371769 0.654669 0.121 Uiso 1 1 calc R U . . .
C17 C 0.4521(7) 0.4620(3) 0.6905(2) 0.1078(16) Uani 1 1 d . . . . .
H17 H 0.451797 0.444951 0.741091 0.129 Uiso 1 1 calc R U . . .
C24 C 0.5920(6) 0.6779(3) -0.0674(2) 0.1011(14) Uani 1 1 d . . . . .
H24 H 0.593994 0.689072 -0.119316 0.121 Uiso 1 1 calc R U . . .
C25 C 0.6873(6) 0.6217(3) -0.0381(3) 0.1008(14) Uani 1 1 d . . . . .
H25 H 0.755402 0.593435 -0.069474 0.121 Uiso 1 1 calc R U . . .
C2 C 0.4876(8) 0.8988(4) 0.5917(2) 0.135(2) Uani 1 1 d . . . . .
H2A H 0.548211 0.949023 0.592368 0.202 Uiso 1 1 calc R U . . .
H2B H 0.538330 0.855370 0.619799 0.202 Uiso 1 1 calc R U . . .
H2C H 0.390436 0.910108 0.614388 0.202 Uiso 1 1 calc R U . . .
C28 C 0.3851(7) 0.7987(3) 0.4937(2) 0.1038(15) Uani 1 1 d . . . . .
H28 H 0.348010 0.766073 0.533424 0.125 Uiso 1 1 calc R U . . .
C8 C 0.7803(7) 0.8068(4) 0.2509(5) 0.158(3) Uani 1 1 d . . . . .
H8 H 0.777033 0.844999 0.290935 0.190 Uiso 1 1 calc R U . . .
C9 C 0.8840(11) 0.7670(5) 0.2516(6) 0.204(4) Uani 1 1 d . . . . .
H9A H 0.898647 0.726649 0.214022 0.244 Uiso 1 1 calc R U . . .
H9B H 0.956133 0.773983 0.289700 0.244 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 O2 1.424(3) . ?
S O5 1.426(3) . ?
S N 1.633(3) . ?
S C6 1.758(3) . ?
O1 C11 1.379(5) . ?
O1 C10 1.410(4) . ?
O3 C11 1.184(4) . ?
N C10 1.402(4) . ?
N C1 1.479(5) . ?
C21 C10 1.312(4) . ?
C21 C22 1.470(5) . ?
C21 H21 0.9300 . ?
C6 C5 1.370(5) . ?
C6 C7 1.384(5) . ?
C22 C20 1.372(5) . ?
C22 C26 1.374(5) . ?
C11 C12 1.443(5) . ?
C14 C19 1.378(5) . ?
C14 C15 1.385(6) . ?
C14 C13 1.427(5) . ?
C13 C12 1.190(5) . ?
C5 C4 1.379(5) . ?
C5 H5 0.9300 . ?
C19 C18 1.377(5) . ?
C19 H19 0.9300 . ?
C20 C23 1.386(5) . ?
C20 H20 0.9300 . ?
C15 C16 1.375(6) . ?
C15 H15 0.9300 . ?
C23 C24 1.366(6) . ?
C23 H23 0.9300 . ?
C4 C3 1.365(6) . ?
C4 H4 0.9300 . ?
C16 C17 1.368(7) . ?
C16 H16 0.9300 . ?
C7 C28 1.387(5) . ?
C7 H7 0.9300 . ?
C26 C25 1.381(6) . ?
C26 H26 0.9300 . ?
C1 C8 1.467(8) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C3 C28 1.370(6) . ?
C3 C2 1.516(6) . ?
C18 C17 1.340(7) . ?
C18 H18 0.9300 . ?
C17 H17 0.9300 . ?
C24 C25 1.329(6) . ?
C24 H24 0.9300 . ?
C25 H25 0.9300 . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C28 H28 0.9300 . ?
C8 C9 1.110(9) . ?
C8 H8 0.9300 . ?
C9 H9A 0.9300 . ?
C9 H9B 0.9300 . ?

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
O2 S O5 120.86(18) . . ?
O2 S N 106.32(16) . . ?
O5 S N 105.56(15) . . ?
O2 S C6 107.12(16) . . ?
O5 S C6 107.97(17) . . ?
N S C6 108.55(16) . . ?
C11 O1 C10 117.9(3) . . ?
C10 N C1 118.3(3) . . ?
C10 N S 120.4(2) . . ?
C1 N S 120.6(2) . . ?
C10 C21 C22 128.5(3) . . ?
C10 C21 H21 115.7 . . ?
C22 C21 H21 115.7 . . ?
C5 C6 C7 119.9(3) . . ?
C5 C6 S 119.8(3) . . ?
C7 C6 S 120.2(3) . . ?
C20 C22 C26 117.1(3) . . ?
C20 C22 C21 123.5(3) . . ?
C26 C22 C21 119.3(4) . . ?
O3 C11 O1 125.9(3) . . ?
O3 C11 C12 125.3(4) . . ?
O1 C11 C12 108.8(4) . . ?
C21 C10 O1 122.0(3) . . ?
C21 C10 N 126.8(3) . . ?
O1 C10 N 110.8(3) . . ?
C19 C14 C15 119.5(3) . . ?
C19 C14 C13 120.0(4) . . ?
C15 C14 C13 120.5(4) . . ?
C12 C13 C14 179.1(5) . . ?
C13 C12 C11 175.3(5) . . ?
C6 C5 C4 119.8(4) . . ?
C6 C5 H5 120.1 . . ?
C4 C5 H5 120.1 . . ?
C18 C19 C14 120.0(4) . . ?
C18 C19 H19 120.0 . . ?
C14 C19 H19 120.0 . . ?
C22 C20 C23 120.8(4) . . ?
C22 C20 H20 119.6 . . ?
C23 C20 H20 119.6 . . ?
C16 C15 C14 119.5(4) . . ?
C16 C15 H15 120.3 . . ?
C14 C15 H15 120.3 . . ?
C24 C23 C20 119.9(4) . . ?
C24 C23 H23 120.0 . . ?
C20 C23 H23 120.0 . . ?
C3 C4 C5 121.8(4) . . ?
C3 C4 H4 119.1 . . ?
C5 C4 H4 119.1 . . ?
C15 C16 C17 119.7(5) . . ?
C15 C16 H16 120.1 . . ?
C17 C16 H16 120.1 . . ?
C6 C7 C28 118.6(4) . . ?
C6 C7 H7 120.7 . . ?
C28 C7 H7 120.7 . . ?
C25 C26 C22 121.9(4) . . ?
C25 C26 H26 119.1 . . ?
C22 C26 H26 119.1 . . ?
C8 C1 N 111.7(4) . . ?
C8 C1 H1A 109.3 . . ?
N C1 H1A 109.3 . . ?
C8 C1 H1B 109.3 . . ?
N C1 H1B 109.3 . . ?
H1A C1 H1B 107.9 . . ?
C4 C3 C28 117.8(4) . . ?
C4 C3 C2 121.0(5) . . ?
C28 C3 C2 121.1(5) . . ?
C17 C18 C19 120.0(5) . . ?
C17 C18 H18 120.0 . . ?
C19 C18 H18 120.0 . . ?
C18 C17 C16 121.4(4) . . ?
C18 C17 H17 119.3 . . ?
C16 C17 H17 119.3 . . ?
C25 C24 C23 120.4(4) . . ?
C25 C24 H24 119.8 . . ?
C23 C24 H24 119.8 . . ?
C24 C25 C26 119.9(4) . . ?
C24 C25 H25 120.0 . . ?
C26 C25 H25 120.0 . . ?
C3 C2 H2A 109.5 . . ?
C3 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
C3 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C3 C28 C7 122.1(4) . . ?
C3 C28 H28 118.9 . . ?
C7 C28 H28 118.9 . . ?
C9 C8 C1 134.2(9) . . ?
C9 C8 H8 112.9 . . ?
C1 C8 H8 112.9 . . ?
C8 C9 H9A 120.0 . . ?
C8 C9 H9B 120.0 . . ?
H9A C9 H9B 120.0 . . ?

_refine_diff_density_max         0.147
_refine_diff_density_min         -0.201
_refine_diff_density_rms         0.032

