# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 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_cu_20181221zh_nannong_zhu_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1887624'
loop_
_audit_author_name
_audit_author_address
g
;Nanjing Agricultural University
China
;
_audit_update_record             
;
2022-03-07 deposited with the CCDC.	2022-11-08 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            'C26 H24 N2 S'
_chemical_formula_weight         396.53

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      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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'

_cell_length_a                   5.9714(6)
_cell_length_b                   7.5838(7)
_cell_length_c                   23.115(2)
_cell_angle_alpha                90
_cell_angle_beta                 96.615(3)
_cell_angle_gamma                90
_cell_volume                     1039.80(17)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    6809
_cell_measurement_theta_min      6.15
_cell_measurement_theta_max      68.51

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.267
_exptl_crystal_F_000             420
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.140
_exptl_absorpt_coefficient_mu    1.475
_shelx_estimated_absorpt_T_min   0.737
_shelx_estimated_absorpt_T_max   0.820
_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      173(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\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            6701
_diffrn_reflns_av_unetI/netI     0.0479
_diffrn_reflns_av_R_equivalents  0.0268
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         6.145
_diffrn_reflns_theta_max         64.980
_diffrn_reflns_theta_full        64.980
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measured_fraction_theta_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.921
_diffrn_reflns_point_group_measured_fraction_full 0.922
_reflns_number_total             3237
_reflns_number_gt                3203
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.727
_reflns_Friedel_fraction_max     0.847
_reflns_Friedel_fraction_full    0.847

_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 2014/5 (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)+(0.0557P)²+0.1496P] 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 1324 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.066(7)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         3237
_refine_ls_number_parameters     258
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0343
_refine_ls_R_factor_gt           0.0341
_refine_ls_wR_factor_ref         0.0932
_refine_ls_wR_factor_gt          0.0930
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.036
_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
C1 C 0.9445(6) 0.1727(5) 0.45076(14) 0.0506(7) Uani 1 1 d . . . . .
H1 H 1.053260 0.115560 0.477652 0.061 Uiso 1 1 calc R U . . .
C2 C 0.9751(6) 0.1762(5) 0.39264(15) 0.0601(9) Uani 1 1 d . . . . .
H2 H 1.104194 0.121743 0.379959 0.072 Uiso 1 1 calc R U . . .
C3 C 0.8199(7) 0.2582(5) 0.35268(13) 0.0569(9) Uani 1 1 d . . . . .
H3 H 0.841833 0.261899 0.312636 0.068 Uiso 1 1 calc R U . . .
C4 C 0.6327(7) 0.3346(5) 0.37174(14) 0.0581(9) Uani 1 1 d . . . . .
H4 H 0.523777 0.390256 0.344536 0.070 Uiso 1 1 calc R U . . .
C5 C 0.6017(6) 0.3312(5) 0.42971(13) 0.0498(7) Uani 1 1 d . . . . .
H5 H 0.471049 0.384680 0.441875 0.060 Uiso 1 1 calc R U . . .
C6 C 0.7570(5) 0.2513(3) 0.47098(11) 0.0331(5) Uani 1 1 d . . . . .
C7 C 0.7273(4) 0.2508(3) 0.53418(11) 0.0312(5) Uani 1 1 d . . . . .
C8 C 0.8867(5) 0.1749(4) 0.57560(12) 0.0429(7) Uani 1 1 d . . . . .
H8 H 1.014592 0.118306 0.563045 0.051 Uiso 1 1 calc R U . . .
C9 C 0.8640(5) 0.1796(4) 0.63415(12) 0.0439(7) Uani 1 1 d . . . . .
H9 H 0.975716 0.125817 0.661072 0.053 Uiso 1 1 calc R U . . .
C10 C 0.6809(5) 0.2614(3) 0.65448(11) 0.0339(5) Uani 1 1 d . . . . .
C11 C 0.5181(5) 0.3322(4) 0.61399(12) 0.0433(6) Uani 1 1 d . . . . .
H11 H 0.388217 0.385141 0.626738 0.052 Uiso 1 1 calc R U . . .
C12 C 0.5405(5) 0.3276(4) 0.55537(12) 0.0413(6) Uani 1 1 d . . . . .
H12 H 0.425579 0.378179 0.528607 0.050 Uiso 1 1 calc R U . . .
C13 C 0.6747(5) 0.2805(4) 0.71978(11) 0.0362(6) Uani 1 1 d . . . . .
H13 H 0.783888 0.193827 0.739703 0.043 Uiso 1 1 calc R U . . .
C14 C 0.4497(5) 0.2394(4) 0.73659(11) 0.0440(7) Uani 1 1 d . . . . .
C15 C 0.7506(5) 0.4668(4) 0.74065(11) 0.0376(6) Uani 1 1 d . . . . .
H15A H 0.903427 0.489441 0.729663 0.045 Uiso 1 1 calc R U . . .
H15B H 0.647143 0.554841 0.720415 0.045 Uiso 1 1 calc R U . . .
C16 C 0.7545(4) 0.4912(4) 0.80643(11) 0.0339(5) Uani 1 1 d . . . . .
H16A H 0.835824 0.390448 0.826338 0.041 Uiso 1 1 calc R U . . .
H16B H 0.597520 0.488154 0.816260 0.041 Uiso 1 1 calc R U . . .
C17 C 0.8667(4) 0.6645(4) 0.83052(10) 0.0341(6) Uani 1 1 d . . . . .
C18 C 1.1189(5) 0.6623(5) 0.82384(13) 0.0526(8) Uani 1 1 d . . . . .
H18A H 1.139333 0.662315 0.782382 0.079 Uiso 1 1 calc R U . . .
H18B H 1.187788 0.556127 0.842348 0.079 Uiso 1 1 calc R U . . .
H18C H 1.190868 0.767133 0.842532 0.079 Uiso 1 1 calc R U . . .
C19 C 0.7531(6) 0.8253(4) 0.80060(13) 0.0521(8) Uani 1 1 d . . . . .
H19A H 0.590955 0.821175 0.803750 0.078 Uiso 1 1 calc R U . . .
H19B H 0.777938 0.825494 0.759425 0.078 Uiso 1 1 calc R U . . .
H19C H 0.817389 0.932666 0.819374 0.078 Uiso 1 1 calc R U . . .
C20 C 0.8347(4) 0.6699(3) 0.89470(10) 0.0283(5) Uani 1 1 d . . . . .
C21 C 0.6791(4) 0.7168(3) 0.97573(11) 0.0318(5) Uani 1 1 d . . . . .
C22 C 0.8741(4) 0.6296(3) 0.99985(11) 0.0313(5) Uani 1 1 d . . . . .
C23 C 0.9178(5) 0.5960(4) 1.05951(11) 0.0412(6) Uani 1 1 d . . . . .
H23 H 1.052517 0.539091 1.075573 0.049 Uiso 1 1 calc R U . . .
C24 C 0.7562(6) 0.6492(4) 1.09415(12) 0.0505(8) Uani 1 1 d . . . . .
H24 H 0.777873 0.626037 1.134801 0.061 Uiso 1 1 calc R U . . .
C25 C 0.5610(6) 0.7367(4) 1.07003(14) 0.0510(8) Uani 1 1 d . . . . .
H25 H 0.453131 0.772547 1.094822 0.061 Uiso 1 1 calc R U . . .
C26 C 0.5218(5) 0.7719(4) 1.01190(13) 0.0421(6) Uani 1 1 d . . . . .
H26 H 0.389410 0.832864 0.996365 0.051 Uiso 1 1 calc R U . . .
N1 N 0.2768(5) 0.2089(5) 0.75027(12) 0.0687(9) Uani 1 1 d . . . . .
N2 N 0.6585(4) 0.7398(3) 0.91518(9) 0.036 Uani 1 1 d . . . . .
S1 S 1.03711(10) 0.57230(9) 0.94571(2) 0.03717(19) 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 1.377(5) . ?
C1 C6 1.396(4) . ?
C1 H1 0.9500 . ?
C2 C3 1.379(6) . ?
C2 H2 0.9500 . ?
C3 C4 1.376(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.374(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.390(4) . ?
C5 H5 0.9500 . ?
C6 C7 1.492(3) . ?
C7 C8 1.394(4) . ?
C7 C12 1.397(4) . ?
C8 C9 1.376(4) . ?
C8 H8 0.9500 . ?
C9 C10 1.386(4) . ?
C9 H9 0.9500 . ?
C10 C11 1.378(4) . ?
C10 C13 1.521(3) . ?
C11 C12 1.377(4) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 C14 1.475(4) . ?
C13 C15 1.544(4) . ?
C13 H13 1.0000 . ?
C14 N1 1.138(4) . ?
C15 C16 1.529(3) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.549(4) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C20 1.518(3) . ?
C17 C19 1.522(4) . ?
C17 C18 1.531(4) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 N2 1.314(3) . ?
C20 S1 1.752(2) . ?
C21 C26 1.392(4) . ?
C21 C22 1.398(4) . ?
C21 N2 1.402(3) . ?
C22 C23 1.397(4) . ?
C22 S1 1.727(2) . ?
C23 C24 1.383(5) . ?
C23 H23 0.9500 . ?
C24 C25 1.400(5) . ?
C24 H24 0.9500 . ?
C25 C26 1.363(5) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?

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 C6 121.3(3) . . ?
C2 C1 H1 119.3 . . ?
C6 C1 H1 119.3 . . ?
C1 C2 C3 120.5(3) . . ?
C1 C2 H2 119.7 . . ?
C3 C2 H2 119.7 . . ?
C4 C3 C2 118.9(3) . . ?
C4 C3 H3 120.5 . . ?
C2 C3 H3 120.5 . . ?
C5 C4 C3 120.7(3) . . ?
C5 C4 H4 119.7 . . ?
C3 C4 H4 119.7 . . ?
C4 C5 C6 121.5(3) . . ?
C4 C5 H5 119.2 . . ?
C6 C5 H5 119.2 . . ?
C5 C6 C1 117.0(3) . . ?
C5 C6 C7 121.9(2) . . ?
C1 C6 C7 121.1(3) . . ?
C8 C7 C12 116.2(2) . . ?
C8 C7 C6 121.7(2) . . ?
C12 C7 C6 122.1(2) . . ?
C9 C8 C7 121.9(3) . . ?
C9 C8 H8 119.1 . . ?
C7 C8 H8 119.1 . . ?
C8 C9 C10 121.1(3) . . ?
C8 C9 H9 119.5 . . ?
C10 C9 H9 119.5 . . ?
C11 C10 C9 117.8(2) . . ?
C11 C10 C13 122.8(2) . . ?
C9 C10 C13 119.3(2) . . ?
C12 C11 C10 121.2(3) . . ?
C12 C11 H11 119.4 . . ?
C10 C11 H11 119.4 . . ?
C11 C12 C7 121.8(3) . . ?
C11 C12 H12 119.1 . . ?
C7 C12 H12 119.1 . . ?
C14 C13 C10 111.6(2) . . ?
C14 C13 C15 110.8(2) . . ?
C10 C13 C15 110.9(2) . . ?
C14 C13 H13 107.8 . . ?
C10 C13 H13 107.8 . . ?
C15 C13 H13 107.8 . . ?
N1 C14 C13 179.0(3) . . ?
C16 C15 C13 113.1(2) . . ?
C16 C15 H15A 109.0 . . ?
C13 C15 H15A 109.0 . . ?
C16 C15 H15B 109.0 . . ?
C13 C15 H15B 109.0 . . ?
H15A C15 H15B 107.8 . . ?
C15 C16 C17 114.6(2) . . ?
C15 C16 H16A 108.6 . . ?
C17 C16 H16A 108.6 . . ?
C15 C16 H16B 108.6 . . ?
C17 C16 H16B 108.6 . . ?
H16A C16 H16B 107.6 . . ?
C20 C17 C19 108.8(2) . . ?
C20 C17 C18 109.6(2) . . ?
C19 C17 C18 110.8(3) . . ?
C20 C17 C16 106.04(19) . . ?
C19 C17 C16 111.4(2) . . ?
C18 C17 C16 110.1(2) . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C17 C19 H19A 109.5 . . ?
C17 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C17 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
N2 C20 C17 124.0(2) . . ?
N2 C20 S1 116.54(19) . . ?
C17 C20 S1 119.43(17) . . ?
C26 C21 C22 119.4(3) . . ?
C26 C21 N2 125.1(2) . . ?
C22 C21 N2 115.5(2) . . ?
C23 C22 C21 122.2(2) . . ?
C23 C22 S1 127.8(2) . . ?
C21 C22 S1 110.06(19) . . ?
C24 C23 C22 117.1(3) . . ?
C24 C23 H23 121.5 . . ?
C22 C23 H23 121.5 . . ?
C23 C24 C25 120.8(3) . . ?
C23 C24 H24 119.6 . . ?
C25 C24 H24 119.6 . . ?
C26 C25 C24 121.7(3) . . ?
C26 C25 H25 119.1 . . ?
C24 C25 H25 119.1 . . ?
C25 C26 C21 118.8(3) . . ?
C25 C26 H26 120.6 . . ?
C21 C26 H26 120.6 . . ?
C20 N2 C21 109.1(2) . . ?
C22 S1 C20 88.77(12) . . ?

_refine_diff_density_max         0.320
_refine_diff_density_min         -0.209
_refine_diff_density_rms         0.040



