# 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_1
_database_code_depnum_ccdc_archive 'CCDC 2159105'
loop_
_audit_author_name
_audit_author_address
'Craig Forsyth'
;Monash University
Australia
;
_audit_update_record             
;
2022-03-15 deposited with the CCDC.	2022-06-12 downloaded from the CCDC.
;
_audit_creation_date             2018-07-28
_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         'C28 H24 Cl N O4 S'
_chemical_formula_sum            'C28 H24 Cl N O4 S'
_chemical_formula_weight         505.99
_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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      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                   9.8638(4)
_cell_length_b                   10.1729(3)
_cell_length_c                   13.2234(5)
_cell_angle_alpha                98.270(3)
_cell_angle_beta                 94.546(3)
_cell_angle_gamma                114.109(3)
_cell_volume                     1184.47(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4849
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      26
_cell_measurement_theta_min      2
_shelx_estimated_absorpt_T_max   0.966
_shelx_estimated_absorpt_T_min   0.932
_exptl_absorpt_coefficient_mu    0.286
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.62171
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.419
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0538
_diffrn_reflns_av_unetI/netI     0.0366
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            24865
_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         26.371
_diffrn_reflns_theta_min         2.473
_diffrn_ambient_temperature      123(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'XtaLAB Synergy Dualflex HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  mirror
_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                4138
_reflns_number_total             4849
_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_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_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 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.492
_refine_diff_density_min         -0.388
_refine_diff_density_rms         0.056
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     318
_refine_ls_number_reflns         4849
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0464
_refine_ls_R_factor_gt           0.0391
_refine_ls_restrained_S_all      1.048
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0589P)²+0.4490P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1049
_refine_ls_wR_factor_ref         0.1103
_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), C11(H11A,H11B), C13(H13A,H13B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C6(H6), C5(H5), C23(H23), C25(H25), C15(H15), C22(H22), C19(H19),
 C21(H21), C17(H17), C16(H16), C18(H18)
2.c Idealised Me refined as rotating group:
 C26(H26A,H26B,H26C), C28(H28A,H28B,H28C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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 0.07507(4) 0.73416(4) 0.91424(3) 0.02078(12) Uani 1 1 d . . . . .
Cl1 Cl 0.41128(6) 0.94657(5) 0.31729(4) 0.03749(14) Uani 1 1 d . . . . .
O3 O -0.00177(13) 0.88487(12) 0.70586(9) 0.0226(3) Uani 1 1 d . . . . .
O1 O -0.00822(13) 0.65172(13) 0.98537(9) 0.0258(3) Uani 1 1 d . . . . .
O2 O 0.08262(14) 0.87665(13) 0.91155(9) 0.0255(3) Uani 1 1 d . . . . .
O4 O 0.22109(15) 1.07832(14) 0.76960(10) 0.0313(3) Uani 1 1 d . . . . .
N1 N -0.00649(15) 0.63153(15) 0.79672(11) 0.0215(3) Uani 1 1 d . . . . .
C9 C 0.06225(17) 0.68172(17) 0.70928(12) 0.0203(3) Uani 1 1 d . . . . .
C4 C 0.14481(18) 0.83017(18) 0.58042(12) 0.0218(3) Uani 1 1 d . . . . .
C8 C 0.11650(18) 0.58326(17) 0.66079(13) 0.0213(3) Uani 1 1 d . . . . .
C10 C 0.07075(18) 0.80003(17) 0.66781(13) 0.0206(3) Uani 1 1 d . . . . .
C3 C 0.20864(18) 0.73583(18) 0.53633(12) 0.0213(3) Uani 1 1 d . . . . .
C20 C 0.25895(18) 0.74733(18) 0.93312(13) 0.0224(3) Uani 1 1 d . . . . .
C7 C 0.18794(19) 0.60633(18) 0.57605(13) 0.0224(3) Uani 1 1 d . . . . .
C2 C 0.29149(19) 0.77560(19) 0.45389(13) 0.0252(4) Uani 1 1 d . . . . .
H2 H 0.337803 0.716688 0.424644 0.030 Uiso 1 1 calc R . . . .
C27 C 0.0873(2) 1.02459(18) 0.76154(13) 0.0253(4) Uani 1 1 d . . . . .
C14 C 0.37321(19) 0.49785(18) 0.60111(13) 0.0232(3) Uani 1 1 d . . . . .
C24 C 0.54756(19) 0.76156(19) 0.95837(13) 0.0265(4) Uani 1 1 d . . . . .
C6 C 0.2363(2) 0.98701(19) 0.45548(13) 0.0271(4) Uani 1 1 d . . . . .
H6 H 0.244293 1.069701 0.426623 0.032 Uiso 1 1 calc R . . . .
C5 C 0.15783(19) 0.95257(18) 0.53571(13) 0.0244(4) Uani 1 1 d . . . . .
H5 H 0.110707 1.012204 0.562295 0.029 Uiso 1 1 calc R . . . .
C23 C 0.5133(2) 0.8531(2) 0.90208(14) 0.0293(4) Uani 1 1 d . . . . .
H23 H 0.589899 0.920520 0.871964 0.035 Uiso 1 1 calc R . . . .
C1 C 0.3050(2) 0.89787(19) 0.41641(13) 0.0261(4) Uani 1 1 d . . . . .
C12 C -0.03107(19) 0.47392(18) 0.78550(14) 0.0246(4) Uani 1 1 d . . . . .
H12A H -0.135081 0.407420 0.752158 0.030 Uiso 1 1 calc R . . . .
H12B H -0.013461 0.450201 0.853959 0.030 Uiso 1 1 calc R . . . .
C11 C 0.0823(2) 0.45793(18) 0.71779(13) 0.0243(4) Uani 1 1 d . . . . .
H11A H 0.174060 0.467256 0.760509 0.029 Uiso 1 1 calc R . . . .
H11B H 0.038060 0.362235 0.669146 0.029 Uiso 1 1 calc R . . . .
C13 C 0.2434(2) 0.49589(18) 0.52974(13) 0.0249(4) Uani 1 1 d . . . . .
H13A H 0.276469 0.518231 0.462973 0.030 Uiso 1 1 calc R . . . .
H13B H 0.159693 0.396377 0.515870 0.030 Uiso 1 1 calc R . . . .
C25 C 0.4342(2) 0.6636(2) 1.00174(14) 0.0294(4) Uani 1 1 d . . . . .
H25 H 0.456201 0.601560 1.040969 0.035 Uiso 1 1 calc R . . . .
C15 C 0.3618(2) 0.37420(19) 0.63899(14) 0.0280(4) Uani 1 1 d . . . . .
H15 H 0.272953 0.285585 0.617858 0.034 Uiso 1 1 calc R . . . .
C22 C 0.3701(2) 0.84780(19) 0.88915(14) 0.0265(4) Uani 1 1 d . . . . .
H22 H 0.348307 0.911183 0.851213 0.032 Uiso 1 1 calc R . . . .
C19 C 0.5051(2) 0.62608(19) 0.63169(14) 0.0284(4) Uani 1 1 d . . . . .
H19 H 0.514742 0.711825 0.606421 0.034 Uiso 1 1 calc R . . . .
C21 C 0.2891(2) 0.6545(2) 0.98886(14) 0.0277(4) Uani 1 1 d . . . . .
H21 H 0.211943 0.585785 1.017801 0.033 Uiso 1 1 calc R . . . .
C17 C 0.6082(2) 0.5059(2) 0.73722(15) 0.0335(4) Uani 1 1 d . . . . .
H17 H 0.688078 0.509323 0.784269 0.040 Uiso 1 1 calc R . . . .
C16 C 0.4784(2) 0.3776(2) 0.70740(15) 0.0336(4) Uani 1 1 d . . . . .
H16 H 0.468723 0.292403 0.733391 0.040 Uiso 1 1 calc R . . . .
C26 C 0.7042(2) 0.7710(2) 0.97372(15) 0.0327(4) Uani 1 1 d . . . . .
H26A H 0.737864 0.761263 0.906411 0.049 Uiso 1 1 calc GR . . . .
H26B H 0.704714 0.691930 1.007956 0.049 Uiso 1 1 calc GR . . . .
H26C H 0.772188 0.866111 1.016778 0.049 Uiso 1 1 calc GR . . . .
C28 C -0.0091(2) 1.0924(2) 0.80614(15) 0.0332(4) Uani 1 1 d . . . . .
H28A H -0.090155 1.079359 0.752285 0.050 Uiso 1 1 calc GR . . . .
H28B H 0.052098 1.197426 0.832683 0.050 Uiso 1 1 calc GR . . . .
H28C H -0.052271 1.044922 0.862683 0.050 Uiso 1 1 calc GR . . . .
C18 C 0.6223(2) 0.6296(2) 0.69868(15) 0.0343(4) Uani 1 1 d . . . . .
H18 H 0.712587 0.717196 0.718230 0.041 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 1.4316(12) . ?
S1 O2 1.4266(12) . ?
S1 N1 1.6737(14) . ?
S1 C20 1.7578(17) . ?
Cl1 C1 1.7442(17) . ?
O3 C10 1.3951(19) . ?
O3 C27 1.382(2) . ?
O4 C27 1.193(2) . ?
N1 C9 1.438(2) . ?
N1 C12 1.503(2) . ?
C9 C8 1.417(2) . ?
C9 C10 1.368(2) . ?
C4 C10 1.420(2) . ?
C4 C3 1.431(2) . ?
C4 C5 1.418(2) . ?
C8 C7 1.369(2) . ?
C8 C11 1.508(2) . ?
C3 C7 1.432(2) . ?
C3 C2 1.421(2) . ?
C20 C22 1.393(2) . ?
C20 C21 1.385(2) . ?
C7 C13 1.515(2) . ?
C2 C1 1.365(2) . ?
C27 C28 1.495(2) . ?
C14 C13 1.521(2) . ?
C14 C15 1.386(2) . ?
C14 C19 1.391(2) . ?
C24 C23 1.397(3) . ?
C24 C25 1.388(3) . ?
C24 C26 1.504(2) . ?
C6 C5 1.365(2) . ?
C6 C1 1.404(3) . ?
C23 C22 1.388(3) . ?
C12 C11 1.531(2) . ?
C25 C21 1.391(3) . ?
C15 C16 1.391(3) . ?
C19 C18 1.385(3) . ?
C17 C16 1.380(3) . ?
C17 C18 1.384(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
O1 S1 N1 105.45(7) . . ?
O1 S1 C20 108.74(8) . . ?
O2 S1 O1 119.53(7) . . ?
O2 S1 N1 106.66(7) . . ?
O2 S1 C20 108.73(8) . . ?
N1 S1 C20 107.05(7) . . ?
C27 O3 C10 117.37(13) . . ?
C9 N1 S1 117.88(11) . . ?
C9 N1 C12 105.75(12) . . ?
C12 N1 S1 114.65(11) . . ?
C8 C9 N1 110.77(14) . . ?
C10 C9 N1 128.78(15) . . ?
C10 C9 C8 120.30(15) . . ?
C10 C4 C3 119.63(15) . . ?
C5 C4 C10 121.45(15) . . ?
C5 C4 C3 118.92(15) . . ?
C9 C8 C11 109.01(14) . . ?
C7 C8 C9 122.47(15) . . ?
C7 C8 C11 128.51(15) . . ?
O3 C10 C4 119.68(14) . . ?
C9 C10 O3 120.60(15) . . ?
C9 C10 C4 119.56(15) . . ?
C4 C3 C7 119.69(15) . . ?
C2 C3 C4 117.97(15) . . ?
C2 C3 C7 122.34(15) . . ?
C22 C20 S1 119.32(13) . . ?
C21 C20 S1 119.19(13) . . ?
C21 C20 C22 121.46(16) . . ?
C8 C7 C3 118.02(15) . . ?
C8 C7 C13 118.90(15) . . ?
C3 C7 C13 123.08(15) . . ?
C1 C2 C3 120.47(16) . . ?
O3 C27 C28 109.94(15) . . ?
O4 C27 O3 122.60(16) . . ?
O4 C27 C28 127.45(17) . . ?
C15 C14 C13 121.14(16) . . ?
C15 C14 C19 118.67(17) . . ?
C19 C14 C13 120.17(16) . . ?
C23 C24 C26 120.86(16) . . ?
C25 C24 C23 118.44(16) . . ?
C25 C24 C26 120.68(17) . . ?
C5 C6 C1 118.73(16) . . ?
C6 C5 C4 121.73(16) . . ?
C22 C23 C24 121.52(16) . . ?
C2 C1 Cl1 119.47(14) . . ?
C2 C1 C6 122.03(16) . . ?
C6 C1 Cl1 118.50(13) . . ?
N1 C12 C11 105.75(13) . . ?
C8 C11 C12 103.05(13) . . ?
C7 C13 C14 111.89(13) . . ?
C24 C25 C21 121.29(17) . . ?
C14 C15 C16 121.12(17) . . ?
C23 C22 C20 118.42(16) . . ?
C18 C19 C14 120.49(17) . . ?
C20 C21 C25 118.86(16) . . ?
C16 C17 C18 120.11(18) . . ?
C17 C16 C15 119.45(18) . . ?
C17 C18 C19 120.15(18) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
