# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_lhh-1086a
_database_code_depnum_ccdc_archive 'CCDC 2048086'
loop_
_audit_author_name
_audit_author_address
'Zhiyuan Chen'
;Jiangxi Normal University
China
;
_audit_update_record             
;
2020-12-03 deposited with the CCDC.	2021-03-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C29 H24 N2 O4 S2'
_chemical_formula_weight         528.62

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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.8470(6)
_cell_length_b                   17.2006(14)
_cell_length_c                   16.0137(9)
_cell_angle_alpha                90
_cell_angle_beta                 106.046(6)
_cell_angle_gamma                90
_cell_volume                     2606.6(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    9334
_cell_measurement_theta_min      3.9480
_cell_measurement_theta_max      28.4900

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.347
_exptl_crystal_F_000             1104
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_exptl_absorpt_coefficient_mu    0.243
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.95325
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16179
_diffrn_reflns_av_unetI/netI     0.0276
_diffrn_reflns_av_R_equivalents  0.0330
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.553
_diffrn_reflns_theta_max         25.095
_diffrn_reflns_theta_full        25.095
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             4616
_reflns_number_gt                4059
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0700P)²+0.8718P] 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-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.042(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4616
_refine_ls_number_parameters     335
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0484
_refine_ls_R_factor_gt           0.0414
_refine_ls_wR_factor_ref         0.1181
_refine_ls_wR_factor_gt          0.1127
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_restrained_S_all      1.003
_refine_ls_shift/su_max          0.002
_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
C1 C 0.4892(2) 0.18113(13) 0.75247(12) 0.0413(5) Uani 1 1 d . . . . .
H1A H 0.5158 0.1305 0.7699 0.050 Uiso 1 1 calc R U . . .
C2 C 0.49982(19) 0.24178(12) 0.80641(12) 0.0378(4) Uani 1 1 d . . . . .
C3 C 0.4320(2) 0.38681(13) 0.77313(16) 0.0495(5) Uani 1 1 d . . . . .
H3A H 0.4609 0.4041 0.8304 0.059 Uiso 1 1 calc R U . . .
C4 C 0.3753(2) 0.43797(14) 0.70599(18) 0.0591(6) Uani 1 1 d . . . . .
H4A H 0.3660 0.4902 0.7183 0.071 Uiso 1 1 calc R U . . .
C5 C 0.3322(2) 0.41254(15) 0.62086(17) 0.0588(7) Uani 1 1 d . . . . .
H5A H 0.2939 0.4483 0.5771 0.071 Uiso 1 1 calc R U . . .
C6 C 0.3442(2) 0.33612(15) 0.59865(14) 0.0514(6) Uani 1 1 d . . . . .
H6A H 0.3155 0.3197 0.5411 0.062 Uiso 1 1 calc R U . . .
C7 C 0.40127(18) 0.28447(12) 0.66629(12) 0.0389(5) Uani 1 1 d . . . . .
C8 C 0.44482(18) 0.30893(12) 0.75316(12) 0.0376(4) Uani 1 1 d . . . . .
C9 C 0.2155(2) 0.10341(12) 0.60238(12) 0.0411(5) Uani 1 1 d . . . . .
C10 C 0.0960(2) 0.14947(13) 0.58195(15) 0.0521(6) Uani 1 1 d . . . . .
H10A H 0.0995 0.1998 0.5615 0.063 Uiso 1 1 calc R U . . .
C11 C -0.0280(2) 0.11990(14) 0.59217(17) 0.0591(6) Uani 1 1 d . . . . .
H11A H -0.1084 0.1509 0.5784 0.071 Uiso 1 1 calc R U . . .
C12 C -0.0363(3) 0.04560(15) 0.62221(17) 0.0602(6) Uani 1 1 d . . . . .
C13 C 0.0849(3) 0.00153(16) 0.6433(2) 0.0759(8) Uani 1 1 d . . . . .
H13A H 0.0817 -0.0486 0.6644 0.091 Uiso 1 1 calc R U . . .
C14 C 0.2101(3) 0.02944(14) 0.63394(18) 0.0624(7) Uani 1 1 d . . . . .
H14A H 0.2908 -0.0014 0.6488 0.075 Uiso 1 1 calc R U . . .
C15 C -0.1740(3) 0.0144(2) 0.6327(3) 0.1010(11) Uani 1 1 d . . . . .
H15A H -0.2462 0.0533 0.6148 0.151 Uiso 1 1 calc R U . . .
H15B H -0.2007 -0.0312 0.5974 0.151 Uiso 1 1 calc R U . . .
H15C H -0.1626 0.0013 0.6925 0.151 Uiso 1 1 calc R U . . .
C16 C 0.5575(2) 0.24494(15) 0.90312(13) 0.0537(6) Uani 1 1 d . . . . .
H16A H 0.4789 0.2406 0.9284 0.064 Uiso 1 1 calc R U . . .
H16B H 0.5996 0.2958 0.9186 0.064 Uiso 1 1 calc R U . . .
C17 C 0.66536(19) 0.18448(12) 0.94454(11) 0.0353(4) Uani 1 1 d . . . . .
C18 C 0.8222(2) 0.05842(11) 1.08918(11) 0.0343(4) Uani 1 1 d . . . . .
C19 C 0.6893(2) 0.04188(13) 1.09769(14) 0.0452(5) Uani 1 1 d . . . . .
H19A H 0.6209 0.0805 1.0899 0.054 Uiso 1 1 calc R U . . .
C20 C 0.6607(3) -0.03297(14) 1.11788(16) 0.0590(6) Uani 1 1 d . . . . .
H20A H 0.5712 -0.0455 1.1226 0.071 Uiso 1 1 calc R U . . .
C21 C 0.7629(3) -0.08911(14) 1.13109(17) 0.0665(7) Uani 1 1 d . . . . .
H21A H 0.7435 -0.1392 1.1465 0.080 Uiso 1 1 calc R U . . .
C22 C 0.8943(3) -0.07170(14) 1.12163(18) 0.0665(7) Uani 1 1 d . . . . .
H22A H 0.9628 -0.1104 1.1298 0.080 Uiso 1 1 calc R U . . .
C23 C 0.9253(2) 0.00210(13) 1.10028(15) 0.0501(5) Uani 1 1 d . . . . .
H23A H 1.0138 0.0139 1.0934 0.060 Uiso 1 1 calc R U . . .
C24 C 0.92031(19) 0.19097(10) 1.17989(11) 0.0322(4) Uani 1 1 d . . . . .
C25 C 0.8243(2) 0.22439(14) 1.21694(14) 0.0513(6) Uani 1 1 d . . . . .
H25A H 0.7311 0.2321 1.1847 0.062 Uiso 1 1 calc R U . . .
C26 C 0.8696(3) 0.24636(17) 1.30337(16) 0.0633(7) Uani 1 1 d . . . . .
H26A H 0.8065 0.2697 1.3295 0.076 Uiso 1 1 calc R U . . .
C27 C 1.0070(3) 0.23393(14) 1.35072(14) 0.0526(6) Uani 1 1 d . . . . .
H27A H 1.0358 0.2477 1.4091 0.063 Uiso 1 1 calc R U . . .
C28 C 1.1015(2) 0.20159(13) 1.31280(13) 0.0482(5) Uani 1 1 d . . . . .
H28A H 1.1948 0.1942 1.3452 0.058 Uiso 1 1 calc R U . . .
C29 C 1.0595(2) 0.17977(12) 1.22677(12) 0.0403(5) Uani 1 1 d . . . . .
H29A H 1.1238 0.1578 1.2006 0.048 Uiso 1 1 calc R U . . .
N1 N 0.43186(17) 0.20491(10) 0.66564(10) 0.0421(4) Uani 1 1 d . . . . .
N2 N 0.73966(16) 0.20640(9) 1.02776(10) 0.0379(4) Uani 1 1 d . . . . .
O1 O 0.34142(18) 0.18272(12) 0.50819(9) 0.0654(5) Uani 1 1 d . . . . .
O2 O 0.47504(16) 0.07897(11) 0.60368(11) 0.0654(5) Uani 1 1 d . . . . .
O3 O 0.68284(16) 0.12483(9) 0.90850(8) 0.0484(4) Uani 1 1 d . . . . .
O4 O 0.98988(14) 0.15427(8) 1.03827(8) 0.0436(4) Uani 1 1 d . . . . .
S1 S 0.37306(5) 0.13981(4) 0.58719(3) 0.04630(19) Uani 1 1 d . . . . .
S2 S 0.86938(5) 0.15518(3) 1.07279(3) 0.03143(16) Uani 1 1 d . . . . .


_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
C1 C2 1.340(3) . ?
C1 N1 1.409(2) . ?
C1 H1A 0.9300 . ?
C2 C8 1.449(3) . ?
C2 C16 1.496(3) . ?
C3 C4 1.382(3) . ?
C3 C8 1.391(3) . ?
C3 H3A 0.9300 . ?
C4 C5 1.382(4) . ?
C4 H4A 0.9300 . ?
C5 C6 1.375(4) . ?
C5 H5A 0.9300 . ?
C6 C7 1.394(3) . ?
C6 H6A 0.9300 . ?
C7 N1 1.402(3) . ?
C7 C8 1.402(3) . ?
C9 C14 1.376(3) . ?
C9 C10 1.381(3) . ?
C9 S1 1.751(2) . ?
C10 C11 1.374(3) . ?
C10 H10A 0.9300 . ?
C11 C12 1.376(3) . ?
C11 H11A 0.9300 . ?
C12 C13 1.374(4) . ?
C12 C15 1.510(4) . ?
C13 C14 1.369(3) . ?
C13 H13A 0.9300 . ?
C14 H14A 0.9300 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 C17 1.503(3) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 O3 1.213(2) . ?
C17 N2 1.384(2) . ?
C18 C23 1.379(3) . ?
C18 C19 1.382(3) . ?
C18 S2 1.7669(19) . ?
C19 C20 1.376(3) . ?
C19 H19A 0.9300 . ?
C20 C21 1.368(4) . ?
C20 H20A 0.9300 . ?
C21 C22 1.377(4) . ?
C21 H21A 0.9300 . ?
C22 C23 1.371(3) . ?
C22 H22A 0.9300 . ?
C23 H23A 0.9300 . ?
C24 C25 1.373(3) . ?
C24 C29 1.382(3) . ?
C24 S2 1.7596(17) . ?
C25 C26 1.384(3) . ?
C25 H25A 0.9300 . ?
C26 C27 1.373(3) . ?
C26 H26A 0.9300 . ?
C27 C28 1.363(3) . ?
C27 H27A 0.9300 . ?
C28 C29 1.376(3) . ?
C28 H28A 0.9300 . ?
C29 H29A 0.9300 . ?
N1 S1 1.6628(17) . ?
N2 S2 1.5552(16) . ?
O1 S1 1.4229(16) . ?
O2 S1 1.4236(17) . ?
O4 S2 1.4409(14) . ?

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
C2 C1 N1 110.41(18) . . ?
C2 C1 H1A 124.8 . . ?
N1 C1 H1A 124.8 . . ?
C1 C2 C8 106.93(17) . . ?
C1 C2 C16 129.44(19) . . ?
C8 C2 C16 123.62(19) . . ?
C4 C3 C8 118.5(2) . . ?
C4 C3 H3A 120.8 . . ?
C8 C3 H3A 120.8 . . ?
C5 C4 C3 120.9(2) . . ?
C5 C4 H4A 119.5 . . ?
C3 C4 H4A 119.5 . . ?
C6 C5 C4 122.2(2) . . ?
C6 C5 H5A 118.9 . . ?
C4 C5 H5A 118.9 . . ?
C5 C6 C7 117.0(2) . . ?
C5 C6 H6A 121.5 . . ?
C7 C6 H6A 121.5 . . ?
C6 C7 N1 131.1(2) . . ?
C6 C7 C8 121.8(2) . . ?
N1 C7 C8 107.04(16) . . ?
C3 C8 C7 119.66(18) . . ?
C3 C8 C2 132.47(19) . . ?
C7 C8 C2 107.86(18) . . ?
C14 C9 C10 120.0(2) . . ?
C14 C9 S1 120.53(17) . . ?
C10 C9 S1 119.44(17) . . ?
C11 C10 C9 119.1(2) . . ?
C11 C10 H10A 120.4 . . ?
C9 C10 H10A 120.4 . . ?
C10 C11 C12 121.7(2) . . ?
C10 C11 H11A 119.1 . . ?
C12 C11 H11A 119.1 . . ?
C13 C12 C11 117.8(2) . . ?
C13 C12 C15 121.5(3) . . ?
C11 C12 C15 120.7(2) . . ?
C14 C13 C12 121.8(2) . . ?
C14 C13 H13A 119.1 . . ?
C12 C13 H13A 119.1 . . ?
C13 C14 C9 119.5(2) . . ?
C13 C14 H14A 120.2 . . ?
C9 C14 H14A 120.2 . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C2 C16 C17 116.84(17) . . ?
C2 C16 H16A 108.1 . . ?
C17 C16 H16A 108.1 . . ?
C2 C16 H16B 108.1 . . ?
C17 C16 H16B 108.1 . . ?
H16A C16 H16B 107.3 . . ?
O3 C17 N2 125.60(18) . . ?
O3 C17 C16 123.45(17) . . ?
N2 C17 C16 110.95(17) . . ?
C23 C18 C19 121.7(2) . . ?
C23 C18 S2 117.80(16) . . ?
C19 C18 S2 120.24(15) . . ?
C20 C19 C18 118.5(2) . . ?
C20 C19 H19A 120.7 . . ?
C18 C19 H19A 120.7 . . ?
C21 C20 C19 120.5(2) . . ?
C21 C20 H20A 119.8 . . ?
C19 C20 H20A 119.8 . . ?
C20 C21 C22 120.2(2) . . ?
C20 C21 H21A 119.9 . . ?
C22 C21 H21A 119.9 . . ?
C23 C22 C21 120.6(2) . . ?
C23 C22 H22A 119.7 . . ?
C21 C22 H22A 119.7 . . ?
C22 C23 C18 118.4(2) . . ?
C22 C23 H23A 120.8 . . ?
C18 C23 H23A 120.8 . . ?
C25 C24 C29 121.41(18) . . ?
C25 C24 S2 121.52(14) . . ?
C29 C24 S2 116.96(14) . . ?
C24 C25 C26 118.47(19) . . ?
C24 C25 H25A 120.8 . . ?
C26 C25 H25A 120.8 . . ?
C27 C26 C25 120.4(2) . . ?
C27 C26 H26A 119.8 . . ?
C25 C26 H26A 119.8 . . ?
C28 C27 C26 120.5(2) . . ?
C28 C27 H27A 119.7 . . ?
C26 C27 H27A 119.7 . . ?
C27 C28 C29 120.25(19) . . ?
C27 C28 H28A 119.9 . . ?
C29 C28 H28A 119.9 . . ?
C28 C29 C24 118.97(19) . . ?
C28 C29 H29A 120.5 . . ?
C24 C29 H29A 120.5 . . ?
C7 N1 C1 107.71(16) . . ?
C7 N1 S1 129.22(13) . . ?
C1 N1 S1 120.72(15) . . ?
C17 N2 S2 116.11(14) . . ?
O1 S1 O2 121.07(11) . . ?
O1 S1 N1 105.51(10) . . ?
O2 S1 N1 105.93(9) . . ?
O1 S1 C9 108.92(9) . . ?
O2 S1 C9 108.54(11) . . ?
N1 S1 C9 105.82(9) . . ?
O4 S2 N2 119.09(9) . . ?
O4 S2 C24 109.55(8) . . ?
N2 S2 C24 103.30(9) . . ?
O4 S2 C18 108.97(9) . . ?
N2 S2 C18 112.73(9) . . ?
C24 S2 C18 101.57(8) . . ?

_refine_diff_density_max         0.349
_refine_diff_density_min         -0.302
_refine_diff_density_rms         0.048

