# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_exp_1520_auto
_database_code_depnum_ccdc_archive 'CCDC 2193858'
loop_
_audit_author_name
_audit_author_address
'hui liu'
;shandong university of technology
China
;
_audit_update_record             
;
2022-08-01 deposited with the CCDC.	2022-09-09 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            'C28 H27 N3 O4 S'
_chemical_formula_weight         501.59

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'
S S 0.3331 0.5567 '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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   8.83181(7)
_cell_length_b                   11.23780(12)
_cell_length_c                   13.89801(13)
_cell_angle_alpha                104.4047(9)
_cell_angle_beta                 105.1391(8)
_cell_angle_gamma                101.0237(8)
_cell_volume                     1240.29(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4976
_cell_measurement_theta_min      3.472
_cell_measurement_theta_max      76.909

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.338
_exptl_crystal_F_000             524
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    1.490
_shelx_estimated_absorpt_T_min   0.807
_shelx_estimated_absorpt_T_max   0.865
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            44908
_diffrn_reflns_av_unetI/netI     0.0179
_diffrn_reflns_av_R_equivalents  0.0381
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.472
_diffrn_reflns_theta_max         76.909
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.948
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.948
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.948
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4976
_reflns_number_gt                4634
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0711P)²+1.0533P] 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     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.0015(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4976
_refine_ls_number_parameters     327
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0357
_refine_ls_R_factor_gt           0.0338
_refine_ls_wR_factor_ref         0.0926
_refine_ls_wR_factor_gt          0.0909
_refine_ls_goodness_of_fit_ref   0.740
_refine_ls_restrained_S_all      0.740
_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
S10 S 0.03137(3) 0.33027(3) 0.66864(2) 0.02039(10) Uani 1 1 d . . . . .
O11 O -0.08408(11) 0.21242(9) 0.59879(7) 0.0252(2) Uani 1 1 d . . . . .
O12 O -0.01544(11) 0.44677(9) 0.67495(8) 0.0273(2) Uani 1 1 d . . . . .
O13 O 0.32919(11) 0.55324(8) 0.66151(7) 0.02139(19) Uani 1 1 d . . . . .
O15 O 0.33046(12) 0.66606(9) 0.82345(7) 0.0283(2) Uani 1 1 d . . . . .
N9 N 0.19930(12) 0.33582(10) 0.63547(8) 0.0200(2) Uani 1 1 d . . . . .
N18 N 0.81039(17) 0.08402(14) 1.02193(12) 0.0404(3) Uani 1 1 d . . . . .
N32 N 0.34764(14) 0.76085(10) 0.69869(8) 0.0239(2) Uani 1 1 d . . . . .
C1 C 0.55233(14) 0.33507(12) 0.76551(10) 0.0205(3) Uani 1 1 d . . . . .
C2 C 0.52193(16) 0.34644(12) 0.86089(10) 0.0231(3) Uani 1 1 d . . . . .
H2 H 0.456103 0.399595 0.880337 0.028 Uiso 1 1 calc R U . . .
C3 C 0.58594(16) 0.28165(13) 0.92777(10) 0.0250(3) Uani 1 1 d . . . . .
H3 H 0.564331 0.290580 0.992289 0.030 Uiso 1 1 calc R U . . .
C4 C 0.68203(16) 0.20357(13) 0.89907(11) 0.0249(3) Uani 1 1 d . . . . .
C5 C 0.71089(16) 0.18873(12) 0.80321(11) 0.0252(3) Uani 1 1 d . . . . .
H5 H 0.775557 0.134628 0.783495 0.030 Uiso 1 1 calc R U . . .
C6 C 0.64534(15) 0.25279(12) 0.73706(10) 0.0232(3) Uani 1 1 d . . . . .
H6 H 0.663578 0.240889 0.671336 0.028 Uiso 1 1 calc R U . . .
C7 C 0.49641(15) 0.41217(12) 0.69755(9) 0.0204(3) Uani 1 1 d . . . . .
C8 C 0.33828(15) 0.44585(12) 0.69860(10) 0.0200(2) Uani 1 1 d . . . . .
H8 H 0.337245 0.469801 0.772660 0.024 Uiso 1 1 calc R U . . .
C14 C 0.33524(15) 0.66244(12) 0.73584(10) 0.0220(3) Uani 1 1 d . . . . .
C16 C 0.58260(16) 0.45377(13) 0.64117(11) 0.0262(3) Uani 1 1 d . . . . .
H16A H 0.683366 0.434435 0.643522 0.031 Uiso 1 1 calc R U . . .
H16B H 0.543400 0.502807 0.598564 0.031 Uiso 1 1 calc R U . . .
C17 C 0.75299(17) 0.13731(14) 0.96833(12) 0.0301(3) Uani 1 1 d . . . . .
C19 C 0.09297(15) 0.31704(12) 0.79550(10) 0.0214(3) Uani 1 1 d . . . . .
C20 C 0.11951(16) 0.20150(13) 0.80517(10) 0.0239(3) Uani 1 1 d . . . . .
H20 H 0.110243 0.134322 0.745002 0.029 Uiso 1 1 calc R U . . .
C21 C 0.15944(17) 0.18605(14) 0.90344(11) 0.0289(3) Uani 1 1 d . . . . .
H21 H 0.177433 0.107549 0.910610 0.035 Uiso 1 1 calc R U . . .
C22 C 0.17371(17) 0.28452(15) 0.99242(11) 0.0305(3) Uani 1 1 d . . . . .
C23 C 0.14700(18) 0.39903(14) 0.98058(11) 0.0313(3) Uani 1 1 d . . . . .
H23 H 0.156419 0.466365 1.040688 0.038 Uiso 1 1 calc R U . . .
C24 C 0.10679(16) 0.41672(13) 0.88237(11) 0.0260(3) Uani 1 1 d . . . . .
H24 H 0.089207 0.495246 0.874990 0.031 Uiso 1 1 calc R U . . .
C25 C 0.2183(2) 0.26548(19) 1.09874(12) 0.0449(4) Uani 1 1 d . . . . .
H25A H 0.329910 0.257397 1.118111 0.067 Uiso 1 1 calc R U . . .
H25B H 0.142809 0.187636 1.096222 0.067 Uiso 1 1 calc R U . . .
H25C H 0.211135 0.339017 1.151044 0.067 Uiso 1 1 calc R U . . .
C26 C 0.17475(15) 0.27716(12) 0.52511(10) 0.0203(2) Uani 1 1 d . . . . .
C27 C 0.19684(16) 0.15614(12) 0.49459(10) 0.0237(3) Uani 1 1 d . . . . .
H27 H 0.230642 0.115397 0.545501 0.028 Uiso 1 1 calc R U . . .
C28 C 0.16920(16) 0.09501(13) 0.38916(11) 0.0268(3) Uani 1 1 d . . . . .
H28 H 0.184190 0.012176 0.367754 0.032 Uiso 1 1 calc R U . . .
C29 C 0.11958(17) 0.15493(14) 0.31481(11) 0.0287(3) Uani 1 1 d . . . . .
H29 H 0.100771 0.113009 0.242681 0.034 Uiso 1 1 calc R U . . .
C30 C 0.09757(17) 0.27575(13) 0.34591(11) 0.0279(3) Uani 1 1 d . . . . .
H30 H 0.063624 0.316358 0.294928 0.033 Uiso 1 1 calc R U . . .
C31 C 0.12492(16) 0.33793(12) 0.45142(10) 0.0237(3) Uani 1 1 d . . . . .
H31 H 0.109771 0.420715 0.472828 0.028 Uiso 1 1 calc R U . . .
C33 C 0.34310(18) 0.88636(12) 0.75995(11) 0.0271(3) Uani 1 1 d . . . . .
H33A H 0.447878 0.931791 0.816977 0.032 Uiso 1 1 calc R U . . .
H33B H 0.253680 0.878304 0.790555 0.032 Uiso 1 1 calc R U . . .
C34 C 0.31273(17) 0.95438(13) 0.67730(11) 0.0266(3) Uani 1 1 d . . . . .
H34A H 0.357567 1.048106 0.709578 0.032 Uiso 1 1 calc R U . . .
H34B H 0.194783 0.934254 0.638985 0.032 Uiso 1 1 calc R U . . .
C35 C 0.40363(16) 0.90043(13) 0.60443(11) 0.0262(3) Uani 1 1 d . . . . .
H35A H 0.362167 0.911284 0.534645 0.031 Uiso 1 1 calc R U . . .
H35B H 0.522217 0.942762 0.634887 0.031 Uiso 1 1 calc R U . . .
C36 C 0.36759(17) 0.75919(13) 0.59636(10) 0.0252(3) Uani 1 1 d . . . . .
H36A H 0.266676 0.708162 0.537705 0.030 Uiso 1 1 calc R U . . .
H36B H 0.459258 0.724351 0.586488 0.030 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
S10 O12 1.4357(9) . ?
S10 O11 1.4363(10) . ?
S10 N9 1.6589(10) . ?
S10 C19 1.7571(13) . ?
O13 C14 1.3753(15) . ?
O13 C8 1.4331(14) . ?
O15 C14 1.2202(16) . ?
N9 C26 1.4500(16) . ?
N9 C8 1.4569(16) . ?
N18 C17 1.1452(19) . ?
N32 C14 1.3300(17) . ?
N32 C33 1.4689(16) . ?
N32 C36 1.4741(16) . ?
C1 C2 1.4001(18) . ?
C1 C6 1.4015(18) . ?
C1 C7 1.4879(17) . ?
C2 C3 1.3904(18) . ?
C3 C4 1.3916(19) . ?
C4 C5 1.3968(19) . ?
C4 C17 1.4469(18) . ?
C5 C6 1.3818(18) . ?
C7 C16 1.3303(18) . ?
C7 C8 1.5179(17) . ?
C19 C24 1.3875(19) . ?
C19 C20 1.3949(18) . ?
C20 C21 1.3818(19) . ?
C21 C22 1.398(2) . ?
C22 C23 1.393(2) . ?
C22 C25 1.507(2) . ?
C23 C24 1.392(2) . ?
C26 C27 1.3875(18) . ?
C26 C31 1.3916(18) . ?
C27 C28 1.3880(19) . ?
C28 C29 1.391(2) . ?
C29 C30 1.386(2) . ?
C30 C31 1.3920(19) . ?
C33 C34 1.5264(19) . ?
C34 C35 1.5306(19) . ?
C35 C36 1.5274(18) . ?

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
O12 S10 O11 118.48(6) . . ?
O12 S10 N9 111.51(5) . . ?
O11 S10 N9 105.66(5) . . ?
O12 S10 C19 108.63(6) . . ?
O11 S10 C19 108.68(6) . . ?
N9 S10 C19 102.71(6) . . ?
C14 O13 C8 114.80(9) . . ?
C26 N9 C8 120.24(10) . . ?
C26 N9 S10 115.88(8) . . ?
C8 N9 S10 116.12(8) . . ?
C14 N32 C33 121.20(11) . . ?
C14 N32 C36 125.89(11) . . ?
C33 N32 C36 112.91(10) . . ?
C2 C1 C6 118.12(12) . . ?
C2 C1 C7 121.97(11) . . ?
C6 C1 C7 119.83(11) . . ?
C3 C2 C1 121.47(12) . . ?
C4 C3 C2 119.21(12) . . ?
C3 C4 C5 120.22(12) . . ?
C3 C4 C17 120.28(13) . . ?
C5 C4 C17 119.50(12) . . ?
C6 C5 C4 119.96(12) . . ?
C5 C6 C1 120.97(12) . . ?
C16 C7 C1 122.12(12) . . ?
C16 C7 C8 121.15(12) . . ?
C1 C7 C8 116.68(10) . . ?
O13 C8 N9 111.23(9) . . ?
O13 C8 C7 110.05(10) . . ?
N9 C8 C7 110.21(10) . . ?
O15 C14 N32 125.85(12) . . ?
O15 C14 O13 123.54(12) . . ?
N32 C14 O13 110.60(11) . . ?
N18 C17 C4 178.83(16) . . ?
C24 C19 C20 121.43(12) . . ?
C24 C19 S10 120.60(10) . . ?
C20 C19 S10 117.90(10) . . ?
C21 C20 C19 119.12(13) . . ?
C20 C21 C22 120.81(13) . . ?
C23 C22 C21 118.89(13) . . ?
C23 C22 C25 121.35(14) . . ?
C21 C22 C25 119.76(15) . . ?
C24 C23 C22 121.27(13) . . ?
C19 C24 C23 118.48(13) . . ?
C27 C26 C31 120.89(12) . . ?
C27 C26 N9 117.81(11) . . ?
C31 C26 N9 121.26(11) . . ?
C26 C27 C28 119.55(12) . . ?
C27 C28 C29 120.07(12) . . ?
C30 C29 C28 120.03(12) . . ?
C29 C30 C31 120.39(13) . . ?
C30 C31 C26 119.08(12) . . ?
N32 C33 C34 102.31(11) . . ?
C33 C34 C35 102.99(11) . . ?
C36 C35 C34 103.60(11) . . ?
N32 C36 C35 102.56(10) . . ?

_refine_diff_density_max         0.323
_refine_diff_density_min         -0.474
_refine_diff_density_rms         0.044

