# Supplementary Information (SI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# 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_20250311A_0m_a
_audit_block_doi                 10.5517/ccdc.csd.cc2nw9sn
_database_code_depnum_ccdc_archive 'CCDC 2469112'
loop_
_audit_author_name
_audit_author_address
'Wen Cheng'
;Shanghai Institute of Technology
China
;
_audit_update_record             
;
2025-07-02 deposited with the CCDC.	2026-02-09 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            'C26 H24 N2 O2 S'
_chemical_formula_weight         428.53

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   11.2932(15)
_cell_length_b                   14.2849(18)
_cell_length_c                   14.4944(16)
_cell_angle_alpha                90
_cell_angle_beta                 93.613(5)
_cell_angle_gamma                90
_cell_volume                     2333.6(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    9943
_cell_measurement_theta_min      2.30
_cell_measurement_theta_max      26.93

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.220
_exptl_crystal_F_000             904
_exptl_transmission_factor_min   0.965
_exptl_transmission_factor_max   0.971
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    0.163
_shelx_estimated_absorpt_T_min   0.965
_shelx_estimated_absorpt_T_max   0.971
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      273(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            76409
_diffrn_reflns_av_unetI/netI     0.0246
_diffrn_reflns_av_R_equivalents  0.0842
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.004
_diffrn_reflns_theta_max         25.598
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4387
_reflns_number_gt                3592
_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)+(0.0510P)²+1.2074P] 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_number_reflns         4387
_refine_ls_number_parameters     283
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0551
_refine_ls_R_factor_gt           0.0452
_refine_ls_wR_factor_ref         0.1218
_refine_ls_wR_factor_gt          0.1131
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_restrained_S_all      1.004
_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 0.30343(16) 0.31668(13) 0.77337(13) 0.0443(4) Uani 1 1 d . . . . .
C2 C 0.3273(2) 0.23887(14) 0.72196(15) 0.0570(5) Uani 1 1 d . . . . .
H2 H 0.2940 0.2326 0.6619 0.068 Uiso 1 1 calc R U . . .
C3 C 0.4010(2) 0.17021(15) 0.76003(17) 0.0636(6) Uani 1 1 d . . . . .
H3 H 0.4171 0.1177 0.7251 0.076 Uiso 1 1 calc R U . . .
C4 C 0.45125(18) 0.17798(14) 0.84903(16) 0.0551(5) Uani 1 1 d . . . . .
C5 C 0.4263(2) 0.25661(16) 0.89887(15) 0.0593(5) Uani 1 1 d . . . . .
H5 H 0.4595 0.2629 0.9589 0.071 Uiso 1 1 calc R U . . .
C6 C 0.35315(19) 0.32654(15) 0.86229(14) 0.0534(5) Uani 1 1 d . . . . .
H6 H 0.3376 0.3794 0.8970 0.064 Uiso 1 1 calc R U . . .
C7 C 0.5301(2) 0.10111(17) 0.8891(2) 0.0807(8) Uani 1 1 d . . . . .
H7A H 0.5543 0.1158 0.9521 0.121 Uiso 1 1 calc R U . . .
H7B H 0.5989 0.0956 0.8538 0.121 Uiso 1 1 calc R U . . .
H7C H 0.4873 0.0430 0.8869 0.121 Uiso 1 1 calc R U . . .
C8 C 0.30518(17) 0.48860(13) 0.67735(13) 0.0466(4) Uani 1 1 d . . . . .
C9 C 0.35464(15) 0.57681(12) 0.55673(12) 0.0396(4) Uani 1 1 d . . . . .
C10 C 0.44452(17) 0.61805(13) 0.61366(12) 0.0447(4) Uani 1 1 d . . . . .
C11 C 0.4573(2) 0.58795(16) 0.70539(14) 0.0638(6) Uani 1 1 d . . . . .
C12 C 0.32599(16) 0.60159(12) 0.45839(12) 0.0402(4) Uani 1 1 d . . . . .
C13 C 0.41190(18) 0.62143(16) 0.39677(13) 0.0528(5) Uani 1 1 d . . . . .
H13 H 0.4917 0.6203 0.4168 0.063 Uiso 1 1 calc R U . . .
C14 C 0.3792(2) 0.64286(19) 0.30589(14) 0.0671(6) Uani 1 1 d . . . . .
H14 H 0.4373 0.6555 0.2649 0.080 Uiso 1 1 calc R U . . .
C15 C 0.2621(2) 0.64564(18) 0.27564(15) 0.0705(7) Uani 1 1 d . . . . .
H15 H 0.2408 0.6614 0.2146 0.085 Uiso 1 1 calc R U . . .
C16 C 0.1763(2) 0.62520(18) 0.33514(16) 0.0668(6) Uani 1 1 d . . . . .
H16 H 0.0967 0.6265 0.3144 0.080 Uiso 1 1 calc R U . . .
C17 C 0.20776(18) 0.60268(14) 0.42570(14) 0.0531(5) Uani 1 1 d . . . . .
H17 H 0.1491 0.5880 0.4655 0.064 Uiso 1 1 calc R U . . .
C18 C 0.52135(16) 0.69511(13) 0.58130(12) 0.0427(4) Uani 1 1 d . . . . .
C19 C 0.4773(2) 0.78476(14) 0.57278(16) 0.0601(5) Uani 1 1 d . . . . .
H19 H 0.3991 0.7966 0.5856 0.072 Uiso 1 1 calc R U . . .
C20 C 0.5478(2) 0.85709(15) 0.54546(17) 0.0692(6) Uani 1 1 d . . . . .
H20 H 0.5163 0.9172 0.5408 0.083 Uiso 1 1 calc R U . . .
C21 C 0.6633(2) 0.84279(16) 0.52500(14) 0.0577(5) Uani 1 1 d . . . . .
C22 C 0.70691(19) 0.75312(17) 0.53323(14) 0.0576(5) Uani 1 1 d . . . . .
H22 H 0.7848 0.7415 0.5193 0.069 Uiso 1 1 calc R U . . .
C23 C 0.63830(17) 0.67979(14) 0.56158(14) 0.0515(5) Uani 1 1 d . . . . .
H23 H 0.6706 0.6200 0.5674 0.062 Uiso 1 1 calc R U . . .
C24 C 0.7403(3) 0.9228(2) 0.4958(2) 0.0967(10) Uani 1 1 d . . . . .
H24A H 0.7317 0.9297 0.4298 0.145 Uiso 1 1 calc R U . . .
H24B H 0.8217 0.9099 0.5144 0.145 Uiso 1 1 calc R U . . .
H24C H 0.7162 0.9796 0.5247 0.145 Uiso 1 1 calc R U . . .
C25 C 0.5505(4) 0.6269(3) 0.77347(19) 0.1368(18) Uani 1 1 d . . . . .
H25A H 0.6268 0.6119 0.7501 0.164 Uiso 1 1 calc R U . . .
H25B H 0.5429 0.6946 0.7712 0.164 Uiso 1 1 calc R U . . .
C26 C 0.5562(5) 0.6028(4) 0.8620(3) 0.179(2) Uani 1 1 d . U . . .
H26A H 0.4853 0.6228 0.8895 0.269 Uiso 1 1 calc R U . . .
H26B H 0.6238 0.6322 0.8933 0.269 Uiso 1 1 calc R U . . .
H26C H 0.5636 0.5361 0.8673 0.269 Uiso 1 1 calc R U . . .
N1 N 0.28347(13) 0.51007(10) 0.59013(10) 0.0434(4) Uani 1 1 d . . . . .
N2 N 0.38634(17) 0.52185(13) 0.73785(12) 0.0627(5) Uani 1 1 d . . . . .
O1 O 0.13668(13) 0.36203(11) 0.64920(11) 0.0678(4) Uani 1 1 d . . . . .
O2 O 0.15010(15) 0.44826(11) 0.79766(12) 0.0741(5) Uani 1 1 d . . . . .
S1 S 0.20721(4) 0.40269(3) 0.72450(4) 0.05188(17) 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 1.374(3) . ?
C1 C6 1.380(3) . ?
C1 S1 1.7593(19) . ?
C2 C3 1.379(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.381(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.374(3) . ?
C4 C7 1.507(3) . ?
C5 C6 1.380(3) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 N1 1.309(2) . ?
C8 N2 1.317(3) . ?
C8 S1 1.8145(18) . ?
C9 N1 1.356(2) . ?
C9 C10 1.397(3) . ?
C9 C12 1.484(2) . ?
C10 C11 1.396(3) . ?
C10 C18 1.495(2) . ?
C11 N2 1.342(3) . ?
C11 C25 1.504(3) . ?
C12 C17 1.388(3) . ?
C12 C13 1.389(3) . ?
C13 C14 1.380(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.367(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.369(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.376(3) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C18 C19 1.377(3) . ?
C18 C23 1.386(3) . ?
C19 C20 1.378(3) . ?
C19 H19 0.9300 . ?
C20 C21 1.371(3) . ?
C20 H20 0.9300 . ?
C21 C22 1.375(3) . ?
C21 C24 1.512(3) . ?
C22 C23 1.381(3) . ?
C22 H22 0.9300 . ?
C23 H23 0.9300 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C25 C26 1.326(4) . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
O1 S1 1.4330(17) . ?
O2 S1 1.4319(16) . ?

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 120.44(19) . . ?
C2 C1 S1 118.94(15) . . ?
C6 C1 S1 120.62(15) . . ?
C1 C2 C3 119.5(2) . . ?
C1 C2 H2 120.3 . . ?
C3 C2 H2 120.2 . . ?
C2 C3 C4 121.3(2) . . ?
C2 C3 H3 119.4 . . ?
C4 C3 H3 119.4 . . ?
C5 C4 C3 118.1(2) . . ?
C5 C4 C7 121.9(2) . . ?
C3 C4 C7 120.0(2) . . ?
C4 C5 C6 121.8(2) . . ?
C4 C5 H5 119.1 . . ?
C6 C5 H5 119.1 . . ?
C1 C6 C5 118.89(19) . . ?
C1 C6 H6 120.6 . . ?
C5 C6 H6 120.6 . . ?
C4 C7 H7A 109.5 . . ?
C4 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C4 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N1 C8 N2 129.71(17) . . ?
N1 C8 S1 116.15(15) . . ?
N2 C8 S1 114.12(14) . . ?
N1 C9 C10 120.69(16) . . ?
N1 C9 C12 114.35(15) . . ?
C10 C9 C12 124.94(16) . . ?
C11 C10 C9 117.38(17) . . ?
C11 C10 C18 119.90(17) . . ?
C9 C10 C18 122.63(16) . . ?
N2 C11 C10 121.50(19) . . ?
N2 C11 C25 116.04(19) . . ?
C10 C11 C25 122.5(2) . . ?
C17 C12 C13 118.29(17) . . ?
C17 C12 C9 118.49(16) . . ?
C13 C12 C9 123.19(16) . . ?
C14 C13 C12 120.23(19) . . ?
C14 C13 H13 119.9 . . ?
C12 C13 H13 119.9 . . ?
C15 C14 C13 120.5(2) . . ?
C15 C14 H14 119.7 . . ?
C13 C14 H14 119.7 . . ?
C14 C15 C16 120.0(2) . . ?
C14 C15 H15 120.0 . . ?
C16 C15 H15 120.0 . . ?
C15 C16 C17 120.0(2) . . ?
C15 C16 H16 120.0 . . ?
C17 C16 H16 120.0 . . ?
C16 C17 C12 120.86(19) . . ?
C16 C17 H17 119.6 . . ?
C12 C17 H17 119.6 . . ?
C19 C18 C23 118.16(18) . . ?
C19 C18 C10 119.97(17) . . ?
C23 C18 C10 121.85(17) . . ?
C18 C19 C20 120.7(2) . . ?
C18 C19 H19 119.6 . . ?
C20 C19 H19 119.6 . . ?
C21 C20 C19 121.7(2) . . ?
C21 C20 H20 119.1 . . ?
C19 C20 H20 119.1 . . ?
C20 C21 C22 117.40(19) . . ?
C20 C21 C24 121.3(2) . . ?
C22 C21 C24 121.3(2) . . ?
C21 C22 C23 121.9(2) . . ?
C21 C22 H22 119.1 . . ?
C23 C22 H22 119.1 . . ?
C22 C23 C18 120.09(19) . . ?
C22 C23 H23 120.0 . . ?
C18 C23 H23 120.0 . . ?
C21 C24 H24A 109.5 . . ?
C21 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C21 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C26 C25 C11 121.9(3) . . ?
C26 C25 H25A 106.9 . . ?
C11 C25 H25A 106.9 . . ?
C26 C25 H25B 106.9 . . ?
C11 C25 H25B 106.9 . . ?
H25A C25 H25B 106.7 . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C8 N1 C9 115.50(16) . . ?
C8 N2 C11 115.22(17) . . ?
O2 S1 O1 119.58(11) . . ?
O2 S1 C1 108.36(9) . . ?
O1 S1 C1 108.85(10) . . ?
O2 S1 C8 106.57(9) . . ?
O1 S1 C8 108.07(9) . . ?
C1 S1 C8 104.37(9) . . ?

_refine_diff_density_max         0.496
_refine_diff_density_min         -0.319
_refine_diff_density_rms         0.042

####################################################################### 
# 
# 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_0314-1
_database_code_depnum_ccdc_archive 'CCDC 2366439'
loop_
_audit_author_name
_audit_author_address
'Mengfan LI'
;Shanghai Institute of Technology
China
;
_audit_update_record             
;
2024-06-28 deposited with the CCDC.	2026-02-09 downloaded from the CCDC.
;
_audit_creation_date             2024-03-14
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        .
_chemical_formula_moiety         'C16 H12 N2'
_chemical_formula_sum            'C16 H12 N2'
_chemical_formula_weight         232.28
_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 0.0181 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'

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

_cell_length_a                   11.7603(4)
_cell_length_b                   6.9704(2)
_cell_length_c                   14.8503(6)
_cell_angle_alpha                90
_cell_angle_beta                 91.506(3)
_cell_angle_gamma                90
_cell_volume                     1216.92(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6466
_cell_measurement_temperature    293
_cell_measurement_theta_max      73.6300
_cell_measurement_theta_min      4.7360
_shelx_estimated_absorpt_T_max   0.943
_shelx_estimated_absorpt_T_min   0.843
_exptl_absorpt_coefficient_mu    0.589
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.49a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.268
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             488
_exptl_crystal_preparation       .
_exptl_crystal_recrystallization_method .
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0537
_diffrn_reflns_av_unetI/netI     0.0396
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            10672
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.861
_diffrn_reflns_theta_min         4.736
_diffrn_ambient_temperature      293
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -125.00 -95.00   0.50    0.05    --  -39.95-178.00  60.00   60
  2  ω    -54.00  29.00   0.50    0.05    --  -39.95  57.00   0.00  166
  3  ω    -42.00  39.00   0.50    0.05    --  -39.95  37.00  90.00  162
  4  ω   -107.00 -80.00   0.50    0.05    --  -39.95 -57.00 -60.00   54
  5  ω    -69.00 -43.00   0.50    0.05    --  -39.95-178.00  60.00   52
  6  ω    -50.00 -13.00   0.50    0.05    --  -39.95 -57.00 -60.00   74
  7  ω     70.00 107.00   0.50    0.05    --   39.95 178.00-120.00   74
  8  ω     63.00 114.00   0.50    0.05    --   39.95 178.00 -30.00  102
  9  ω    -51.00 -17.00   0.50    0.18    --  -94.50  45.00 120.00   68
 10  ω    -51.00 -16.00   0.50    0.18    --  -94.50  45.00-150.00   70
 11  ω    -71.00 -42.00   0.50    0.18    --  -94.50  61.00   0.00   58
 12  ω    -46.00 -15.00   0.50    0.18    --  -94.50  45.00 150.00   62
 13  ω    -57.00 -17.00   0.50    0.18    --  -94.50 125.00-120.00   80
 14  ω   -116.00 -82.00   0.50    0.18    --  -94.50-125.00   0.00   68
 15  ω    -71.00 -41.00   0.50    0.18    --  -94.50  61.00  30.00   60
 16  ω   -175.00-127.00   0.50    0.18    --  -94.50 -30.00   0.00   96
 17  ω   -107.00 -81.00   0.50    0.18    --  -94.50 -30.00   0.00   52
 18  ω    -86.00 -47.00   0.50    0.18    --  -94.50 125.00  30.00   78
 19  ω    -51.00 -20.00   0.50    0.18    --  -94.50  45.00 -90.00   62
 20  ω    -51.00 -19.00   0.50    0.18    --  -94.50  45.00 -60.00   64
 21  ω    -51.00 -17.00   0.50    0.18    --  -94.50  45.00-120.00   68
 22  ω     37.00 103.00   0.50    0.18    --  108.87-125.00  60.00  132
 23  ω     71.00 106.00   0.50    0.18    --  108.87 -77.00  30.00   70
 24  ω     77.00 102.00   0.50    0.18    --  108.87-125.00 -90.00   50
 25  ω     48.00  74.00   0.50    0.18    --  108.87-125.00 -90.00   52
 26  ω     48.00 101.00   0.50    0.18    --  108.87 -94.00 -60.00  106
 27  ω     74.00 106.00   0.50    0.18    --  108.87 -77.00 150.00   64
 28  ω    138.00 178.00   0.50    0.18    --  108.87  61.00 -30.00   80
 29  ω     92.00 132.00   0.50    0.18    --  108.87  61.00 -30.00   80
 30  ω     74.00 101.00   0.50    0.18    --  108.87 -94.00 150.00   54
 31  ω     39.00  65.00   0.50    0.18    --  108.87 -61.00  90.00   52
 32  ω     34.00  68.00   0.50    0.18    --  108.87 -94.00 150.00   68
 33  ω     75.00 111.00   0.50    0.18    --  108.87-125.00 -60.00   72
 34  ω    134.00 175.00   0.50    0.18    --  108.87  61.00  90.00   82
 35  ω     80.00 128.00   0.50    0.18    --  108.87  61.00  90.00   96
 36  ω    129.00 157.00   0.50    0.18    --  108.87  45.00-180.00   56
 37  ω     72.00 178.00   0.50    0.18    --  108.87  30.00  60.00  212
 38  ω     86.00 119.00   0.50    0.18    --  108.87  45.00-180.00   66
 39  ω     71.00 104.00   0.50    0.18    --  108.87 -94.00 120.00   66
 40  ω     29.00  72.00   0.50    0.18    --  108.87 -94.00 -90.00   86
 41  ω     82.00 116.00   0.50    0.18    --  108.87-131.00  90.28   68
 42  ω     86.00 111.00   0.50    0.18    --  108.87-125.00 -30.00   50
 43  ω     48.00  78.00   0.50    0.18    --  108.87-131.00  90.28   60
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0992466000
_diffrn_orient_matrix_UB_12      -0.0950678000
_diffrn_orient_matrix_UB_13      -0.0489388000
_diffrn_orient_matrix_UB_21      -0.0702214000
_diffrn_orient_matrix_UB_22      0.0042552000
_diffrn_orient_matrix_UB_23      -0.0889627000
_diffrn_orient_matrix_UB_31      0.0488389000
_diffrn_orient_matrix_UB_32      0.1995477000
_diffrn_orient_matrix_UB_33      -0.0213757000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2159
_reflns_number_total             2413
_reflns_odcompleteness_completeness 99.79
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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_cell_refinement       'CrysAlisPro 1.171.41.49a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.41.49a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.41.49a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.200
_refine_diff_density_min         -0.181
_refine_diff_density_rms         0.036
_refine_ls_extinction_coef       0.0077(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         2413
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0468
_refine_ls_R_factor_gt           0.0435
_refine_ls_restrained_S_all      1.047
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0799P)²+0.0749P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1239
_refine_ls_wR_factor_ref         0.1283
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C5(H5), C6(H6), C8(H8), C9(H9), C12(H12), C13(H13),
 C14(H14), C15(H15), C16(H16)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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
N1 N 0.52106(8) 0.26765(14) 0.49835(7) 0.0534(3) Uani 1 1 d . . . . .
N2 N 0.45551(9) 0.13071(15) 0.63434(8) 0.0614(3) Uani 1 1 d . . . . .
C1 C 0.86503(12) 0.5188(2) 0.35494(10) 0.0656(4) Uani 1 1 d . . . . .
H1 H 0.914623 0.579926 0.316516 0.079 Uiso 1 1 calc R U . . .
C2 C 0.78678(12) 0.3901(2) 0.32093(9) 0.0661(4) Uani 1 1 d . . . . .
H2 H 0.784458 0.362160 0.259677 0.079 Uiso 1 1 calc R U . . .
C3 C 0.71146(11) 0.30213(19) 0.37749(8) 0.0555(3) Uani 1 1 d . . . . .
H3 H 0.657355 0.217416 0.353870 0.067 Uiso 1 1 calc R U . . .
C4 C 0.71589(9) 0.33923(15) 0.46951(7) 0.0460(3) Uani 1 1 d . . . . .
C5 C 0.79667(10) 0.46642(17) 0.50408(9) 0.0542(3) Uani 1 1 d . . . . .
H5 H 0.801532 0.490567 0.565652 0.065 Uiso 1 1 calc R U . . .
C6 C 0.87029(11) 0.55752(19) 0.44610(10) 0.0631(4) Uani 1 1 d . . . . .
H6 H 0.923350 0.645056 0.468869 0.076 Uiso 1 1 calc R U . . .
C7 C 0.62947(9) 0.25236(14) 0.52870(7) 0.0447(3) Uani 1 1 d . . . . .
C8 C 0.44081(11) 0.20558(18) 0.55262(9) 0.0580(3) Uani 1 1 d . . . . .
H8 H 0.366126 0.215703 0.530971 0.070 Uiso 1 1 calc R U . . .
C9 C 0.56302(11) 0.10960(17) 0.66157(8) 0.0548(3) Uani 1 1 d . . . . .
H9 H 0.577271 0.054480 0.717769 0.066 Uiso 1 1 calc R U . . .
C10 C 0.65603(10) 0.16461(15) 0.61148(7) 0.0455(3) Uani 1 1 d . . . . .
C11 C 0.77263(10) 0.12001(15) 0.64600(7) 0.0465(3) Uani 1 1 d . . . . .
C12 C 0.80483(12) 0.16132(17) 0.73501(8) 0.0558(3) Uani 1 1 d . . . . .
H12 H 0.754527 0.224882 0.771994 0.067 Uiso 1 1 calc R U . . .
C13 C 0.91153(14) 0.1081(2) 0.76875(9) 0.0657(4) Uani 1 1 d . . . . .
H13 H 0.932505 0.137359 0.827989 0.079 Uiso 1 1 calc R U . . .
C14 C 0.98625(12) 0.01256(19) 0.71507(10) 0.0654(4) Uani 1 1 d . . . . .
H14 H 1.057378 -0.023557 0.738086 0.079 Uiso 1 1 calc R U . . .
C15 C 0.95555(12) -0.0298(2) 0.62688(10) 0.0629(4) Uani 1 1 d . . . . .
H15 H 1.006170 -0.094326 0.590535 0.076 Uiso 1 1 calc R U . . .
C16 C 0.84964(11) 0.02353(17) 0.59239(8) 0.0537(3) Uani 1 1 d . . . . .
H16 H 0.829699 -0.005295 0.532907 0.064 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
N1 C7 1.3453(15) . ?
N1 C8 1.3294(16) . ?
N2 C8 1.3281(18) . ?
N2 C9 1.3255(18) . ?
C1 H1 0.9300 . ?
C1 C2 1.372(2) . ?
C1 C6 1.380(2) . ?
C2 H2 0.9300 . ?
C2 C3 1.3803(18) . ?
C3 H3 0.9300 . ?
C3 C4 1.3904(17) . ?
C4 C5 1.3880(17) . ?
C4 C7 1.4897(15) . ?
C5 H5 0.9300 . ?
C5 C6 1.3904(18) . ?
C6 H6 0.9300 . ?
C7 C10 1.4010(16) . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?
C9 C10 1.3926(16) . ?
C10 C11 1.4842(16) . ?
C11 C12 1.3954(16) . ?
C11 C16 1.3943(17) . ?
C12 H12 0.9300 . ?
C12 C13 1.389(2) . ?
C13 H13 0.9300 . ?
C13 C14 1.374(2) . ?
C14 H14 0.9300 . ?
C14 C15 1.381(2) . ?
C15 H15 0.9300 . ?
C15 C16 1.3850(19) . ?
C16 H16 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
C8 N1 C7 116.92(11) . . ?
C9 N2 C8 115.00(10) . . ?
C2 C1 H1 120.0 . . ?
C2 C1 C6 120.09(12) . . ?
C6 C1 H1 120.0 . . ?
C1 C2 H2 119.9 . . ?
C1 C2 C3 120.10(13) . . ?
C3 C2 H2 119.9 . . ?
C2 C3 H3 119.8 . . ?
C2 C3 C4 120.49(12) . . ?
C4 C3 H3 119.8 . . ?
C3 C4 C7 119.72(10) . . ?
C5 C4 C3 119.34(11) . . ?
C5 C4 C7 120.82(10) . . ?
C4 C5 H5 120.2 . . ?
C4 C5 C6 119.60(12) . . ?
C6 C5 H5 120.2 . . ?
C1 C6 C5 120.36(12) . . ?
C1 C6 H6 119.8 . . ?
C5 C6 H6 119.8 . . ?
N1 C7 C4 115.18(10) . . ?
N1 C7 C10 121.06(10) . . ?
C10 C7 C4 123.74(10) . . ?
N1 C8 H8 116.4 . . ?
N2 C8 N1 127.18(12) . . ?
N2 C8 H8 116.4 . . ?
N2 C9 H9 117.9 . . ?
N2 C9 C10 124.25(12) . . ?
C10 C9 H9 117.9 . . ?
C7 C10 C11 125.25(10) . . ?
C9 C10 C7 115.39(11) . . ?
C9 C10 C11 119.30(10) . . ?
C12 C11 C10 120.61(11) . . ?
C16 C11 C10 120.79(10) . . ?
C16 C11 C12 118.44(11) . . ?
C11 C12 H12 119.8 . . ?
C13 C12 C11 120.43(13) . . ?
C13 C12 H12 119.8 . . ?
C12 C13 H13 119.8 . . ?
C14 C13 C12 120.37(12) . . ?
C14 C13 H13 119.8 . . ?
C13 C14 H14 120.1 . . ?
C13 C14 C15 119.90(12) . . ?
C15 C14 H14 120.1 . . ?
C14 C15 H15 119.9 . . ?
C14 C15 C16 120.22(13) . . ?
C16 C15 H15 119.9 . . ?
C11 C16 H16 119.7 . . ?
C15 C16 C11 120.64(12) . . ?
C15 C16 H16 119.7 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C7 C10 C9 -4.70(15) . . . . ?
N1 C7 C10 C11 172.39(10) . . . . ?
N2 C9 C10 C7 1.96(17) . . . . ?
N2 C9 C10 C11 -175.31(11) . . . . ?
C1 C2 C3 C4 -1.6(2) . . . . ?
C2 C1 C6 C5 0.2(2) . . . . ?
C2 C3 C4 C5 0.24(19) . . . . ?
C2 C3 C4 C7 176.25(11) . . . . ?
C3 C4 C5 C6 1.27(18) . . . . ?
C3 C4 C7 N1 -46.99(14) . . . . ?
C3 C4 C7 C10 134.66(12) . . . . ?
C4 C5 C6 C1 -1.47(19) . . . . ?
C4 C7 C10 C9 173.56(10) . . . . ?
C4 C7 C10 C11 -9.34(16) . . . . ?
C5 C4 C7 N1 128.97(12) . . . . ?
C5 C4 C7 C10 -49.39(15) . . . . ?
C6 C1 C2 C3 1.4(2) . . . . ?
C7 N1 C8 N2 0.49(19) . . . . ?
C7 C4 C5 C6 -174.70(11) . . . . ?
C7 C10 C11 C12 134.88(11) . . . . ?
C7 C10 C11 C16 -49.81(15) . . . . ?
C8 N1 C7 C4 -174.78(10) . . . . ?
C8 N1 C7 C10 3.62(15) . . . . ?
C8 N2 C9 C10 1.69(17) . . . . ?
C9 N2 C8 N1 -3.11(19) . . . . ?
C9 C10 C11 C12 -48.13(15) . . . . ?
C9 C10 C11 C16 127.18(12) . . . . ?
C10 C11 C12 C13 175.81(11) . . . . ?
C10 C11 C16 C15 -175.43(11) . . . . ?
C11 C12 C13 C14 -0.61(19) . . . . ?
C12 C11 C16 C15 -0.02(18) . . . . ?
C12 C13 C14 C15 0.5(2) . . . . ?
C13 C14 C15 C16 -0.1(2) . . . . ?
C14 C15 C16 C11 -0.1(2) . . . . ?
C16 C11 C12 C13 0.39(17) . . . . ?

_olex2_exptl_crystal_mounting_method .
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.332
_oxdiff_exptl_absorpt_empirical_full_min 0.464
