# Electronic Supplementary Material (ESI) for CrystEngComm.
# 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_SPA532
_database_code_depnum_ccdc_archive 'CCDC 2073010'
loop_
_audit_author_name
_audit_author_address
'Vedichi Madhu'
;Department of Chemistry, Karunya University
India
;
_audit_update_record             
;
2021-03-25 deposited with the CCDC.	2021-08-30 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         'C24 H28 N4 O2 S2'
_chemical_formula_sum            'C24 H28 N4 O2 S2'
_chemical_formula_weight         468.62

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0021 0.0012 '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 0.0044 0.0025 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0080 0.0047 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1022 0.0976 '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                   7.1770(14)
_cell_length_b                   7.4550(15)
_cell_length_c                   11.030(2)
_cell_angle_alpha                105.64(3)
_cell_angle_beta                 97.57(3)
_cell_angle_gamma                90.80(3)
_cell_volume                     562.6(2)
_cell_formula_units_Z            1
_cell_measurement_temperature    220(2)
_cell_measurement_reflns_used    16173
_cell_measurement_theta_min      0.361
_cell_measurement_theta_max      33.548

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.383
_exptl_crystal_F_000             248
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.101
_exptl_crystal_size_mid          0.004
_exptl_crystal_size_min          0.003
_exptl_absorpt_coefficient_mu    0.192
_shelx_estimated_absorpt_T_min   0.981
_shelx_estimated_absorpt_T_max   0.999
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.766
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
'HKL3000sm Scalepack(Otwinowski et.al,2003)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      220(2)
_diffrn_radiation_wavelength     0.630
_diffrn_radiation_type           synchrotron
_diffrn_source                   'PLSII 2D bending magnet'
_diffrn_measurement_device_type  'Rayonix MX225HS CCD area detector'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6355
_diffrn_reflns_av_unetI/netI     0.0632
_diffrn_reflns_av_R_equivalents  0.0455
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.717
_diffrn_reflns_theta_max         26.499
_diffrn_reflns_theta_full        22.210
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             3280
_reflns_number_gt                1989
_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       
'PAL BL2D-SMDC Program(Shin et.al, 2016)'
_computing_cell_refinement       'HKL3000sm(Otwinowski & Minor, 1997)'
_computing_data_reduction        'HKL3000sm(Otwinowski & Minor, 1997)'
_computing_structure_solution    'SHELXT-2018(Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018(Sheldrick, 2018)'
_computing_molecular_graphics    'DIAMOND 4(Putx&Brandenburg, 2014)'
_computing_publication_material  'publCIF(Westrip, 2010)'
_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)+(0.1955P)²+0.0283P] 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         3280
_refine_ls_number_parameters     166
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1284
_refine_ls_R_factor_gt           0.0943
_refine_ls_wR_factor_ref         0.3170
_refine_ls_wR_factor_gt          0.2936
_refine_ls_goodness_of_fit_ref   1.115
_refine_ls_restrained_S_all      1.115
_refine_ls_shift/su_max          0.000
_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
S1 S 0.24198(11) 1.11443(12) 0.48568(9) 0.0627(4) Uani 1 1 d . . . . .
O1 O 0.3460(3) 0.5790(4) 0.6896(3) 0.0664(7) Uani 1 1 d . . . . .
H1 H 0.329330 0.667991 0.658288 0.100 Uiso 1 1 calc R U . . .
N1 N 0.4178(5) 0.8371(4) 0.5808(3) 0.0627(8) Uani 1 1 d . . . . .
N2 N 0.8281(4) 0.2132(5) 0.8229(4) 0.0753(10) Uani 1 1 d . . . . .
C1 C 0.4176(4) 0.9778(5) 0.5203(3) 0.0569(8) Uani 1 1 d . . . . .
C2 C 0.5983(4) 0.7755(4) 0.5845(3) 0.0530(7) Uani 1 1 d . . . . .
C3 C 0.6584(4) 0.6297(4) 0.6440(3) 0.0538(7) Uani 1 1 d . . . . .
C4 C 0.5299(4) 0.5386(5) 0.6962(3) 0.0541(7) Uani 1 1 d . . . . .
C5 C 0.5859(5) 0.4032(5) 0.7553(3) 0.0571(8) Uani 1 1 d . . . . .
H5 H 0.496641 0.344798 0.789307 0.068 Uiso 1 1 calc R U . . .
C6 C 0.7737(5) 0.3505(5) 0.7659(4) 0.0593(8) Uani 1 1 d . . . . .
C7 C 0.9031(5) 0.4406(5) 0.7124(4) 0.0618(9) Uani 1 1 d . . . . .
H7 H 1.029473 0.408173 0.717128 0.074 Uiso 1 1 calc R U . . .
C8 C 0.8458(5) 0.5741(5) 0.6542(4) 0.0593(8) Uani 1 1 d . . . . .
H8 H 0.934717 0.631486 0.619370 0.071 Uiso 1 1 calc R U . . .
C9 C 0.6987(5) 0.1227(5) 0.8802(4) 0.0647(9) Uani 1 1 d . . . . .
H9A H 0.746577 0.001691 0.884414 0.078 Uiso 1 1 calc R U . . .
H9AB H 0.577382 0.098665 0.824827 0.078 Uiso 1 1 calc R U . . .
C10 C 0.6665(6) 0.2316(6) 1.0122(4) 0.0749(10) Uani 1 1 d . . . . .
H10A H 0.580645 0.159824 1.044217 0.112 Uiso 1 1 calc R U . . .
H10B H 0.612780 0.349058 1.008728 0.112 Uiso 1 1 calc R U . . .
H10C H 0.785528 0.255702 1.068292 0.112 Uiso 1 1 calc R U . . .
C11A C 1.0143(8) 0.1362(9) 0.8191(7) 0.0640(18) Uani 0.651(10) 1 d . . P A 1
H11A H 1.060438 0.138945 0.739760 0.077 Uiso 0.651(10) 1 calc R U P A 1
H11B H 1.007316 0.006471 0.822717 0.077 Uiso 0.651(10) 1 calc R U P A 1
C12A C 1.1463(11) 0.2527(11) 0.9316(8) 0.085(2) Uani 0.651(10) 1 d . . P A 1
H12A H 1.164583 0.376964 0.921880 0.127 Uiso 0.651(10) 1 calc R U P A 1
H12B H 1.266491 0.195240 0.936335 0.127 Uiso 0.651(10) 1 calc R U P A 1
H12C H 1.092612 0.260786 1.009060 0.127 Uiso 0.651(10) 1 calc R U P A 1
C11B C 1.0415(18) 0.2378(17) 0.8964(12) 0.059(3) Uani 0.349(10) 1 d . . P A 2
H11C H 1.102285 0.357512 0.898741 0.071 Uiso 0.349(10) 1 calc R U P A 2
H11D H 1.045942 0.226825 0.983237 0.071 Uiso 0.349(10) 1 calc R U P A 2
C12B C 1.1312(14) 0.0733(17) 0.8117(14) 0.075(4) Uani 0.349(10) 1 d . . P A 2
H12D H 1.034047 -0.021310 0.765773 0.113 Uiso 0.349(10) 1 calc R U P A 2
H12E H 1.221668 0.020728 0.864172 0.113 Uiso 0.349(10) 1 calc R U P A 2
H12F H 1.194570 0.116521 0.751562 0.113 Uiso 0.349(10) 1 calc R U P A 2


_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 C1 1.700(3) . ?
S1 C2 1.771(4) 2_676 ?
O1 C4 1.355(3) . ?
O1 H1 0.8300 . ?
N1 C2 1.379(4) . ?
N1 C1 1.387(5) . ?
N2 C6 1.374(5) . ?
N2 C9 1.443(5) . ?
N2 C11A 1.463(6) . ?
N2 C11B 1.619(13) . ?
C1 C1 1.385(7) 2_676 ?
C2 C3 1.457(5) . ?
C3 C4 1.406(5) . ?
C3 C8 1.412(4) . ?
C4 C5 1.380(5) . ?
C5 C6 1.408(4) . ?
C5 H5 0.9400 . ?
C6 C7 1.415(5) . ?
C7 C8 1.364(5) . ?
C7 H7 0.9400 . ?
C8 H8 0.9400 . ?
C9 C10 1.513(6) . ?
C9 H9A 0.9800 . ?
C9 H9AB 0.9800 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 H10C 0.9700 . ?
C11A C12A 1.510(11) . ?
C11A H11A 0.9800 . ?
C11A H11B 0.9800 . ?
C12A H12A 0.9700 . ?
C12A H12B 0.9700 . ?
C12A H12C 0.9700 . ?
C11B C12B 1.534(18) . ?
C11B H11C 0.9800 . ?
C11B H11D 0.9800 . ?
C12B H12D 0.9700 . ?
C12B H12E 0.9700 . ?
C12B H12F 0.9700 . ?

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
C1 S1 C2 88.31(15) . 2_676 ?
C4 O1 H1 109.5 . . ?
C2 N1 C1 105.5(3) . . ?
C6 N2 C9 121.9(3) . . ?
C6 N2 C11A 122.5(4) . . ?
C9 N2 C11A 115.3(4) . . ?
C6 N2 C11B 115.7(5) . . ?
C9 N2 C11B 113.4(5) . . ?
C1 C1 N1 118.5(4) 2_676 . ?
C1 C1 S1 111.2(4) 2_676 . ?
N1 C1 S1 130.3(3) . . ?
N1 C2 C3 122.7(3) . . ?
N1 C2 S1 116.5(3) . 2_676 ?
C3 C2 S1 120.8(2) . 2_676 ?
C4 C3 C8 116.6(3) . . ?
C4 C3 C2 120.7(3) . . ?
C8 C3 C2 122.7(3) . . ?
O1 C4 C5 117.3(3) . . ?
O1 C4 C3 121.5(3) . . ?
C5 C4 C3 121.2(3) . . ?
C4 C5 C6 121.5(3) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 H5 119.3 . . ?
N2 C6 C5 121.3(3) . . ?
N2 C6 C7 121.3(3) . . ?
C5 C6 C7 117.5(3) . . ?
C8 C7 C6 120.4(3) . . ?
C8 C7 H7 119.8 . . ?
C6 C7 H7 119.8 . . ?
C7 C8 C3 122.7(3) . . ?
C7 C8 H8 118.6 . . ?
C3 C8 H8 118.6 . . ?
N2 C9 C10 114.9(4) . . ?
N2 C9 H9A 108.5 . . ?
C10 C9 H9A 108.5 . . ?
N2 C9 H9AB 108.5 . . ?
C10 C9 H9AB 108.5 . . ?
H9A C9 H9AB 107.5 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N2 C11A C12A 108.3(6) . . ?
N2 C11A H11A 110.0 . . ?
C12A C11A H11A 110.0 . . ?
N2 C11A H11B 110.0 . . ?
C12A C11A H11B 110.0 . . ?
H11A C11A H11B 108.4 . . ?
C11A C12A H12A 109.5 . . ?
C11A C12A H12B 109.5 . . ?
H12A C12A H12B 109.5 . . ?
C11A C12A H12C 109.5 . . ?
H12A C12A H12C 109.5 . . ?
H12B C12A H12C 109.5 . . ?
C12B C11B N2 100.7(9) . . ?
C12B C11B H11C 111.6 . . ?
N2 C11B H11C 111.6 . . ?
C12B C11B H11D 111.6 . . ?
N2 C11B H11D 111.6 . . ?
H11C C11B H11D 109.4 . . ?
C11B C12B H12D 109.5 . . ?
C11B C12B H12E 109.5 . . ?
H12D C12B H12E 109.5 . . ?
C11B C12B H12F 109.5 . . ?
H12D C12B H12F 109.5 . . ?
H12E C12B H12F 109.5 . . ?

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
C2 N1 C1 C1 0.2(5) . . . 2_676 ?
C2 N1 C1 S1 -179.3(3) . . . . ?
C2 S1 C1 C1 0.6(4) 2_676 . . 2_676 ?
C2 S1 C1 N1 -179.8(4) 2_676 . . . ?
C1 N1 C2 C3 178.4(3) . . . . ?
C1 N1 C2 S1 -0.7(4) . . . 2_676 ?
N1 C2 C3 C4 2.9(5) . . . . ?
S1 C2 C3 C4 -178.1(2) 2_676 . . . ?
N1 C2 C3 C8 -176.3(3) . . . . ?
S1 C2 C3 C8 2.8(5) 2_676 . . . ?
C8 C3 C4 O1 -178.8(3) . . . . ?
C2 C3 C4 O1 2.0(5) . . . . ?
C8 C3 C4 C5 0.6(5) . . . . ?
C2 C3 C4 C5 -178.6(3) . . . . ?
O1 C4 C5 C6 179.4(3) . . . . ?
C3 C4 C5 C6 0.0(6) . . . . ?
C9 N2 C6 C5 -3.1(7) . . . . ?
C11A N2 C6 C5 170.8(5) . . . . ?
C11B N2 C6 C5 -148.1(6) . . . . ?
C9 N2 C6 C7 178.7(4) . . . . ?
C11A N2 C6 C7 -7.4(7) . . . . ?
C11B N2 C6 C7 33.6(7) . . . . ?
C4 C5 C6 N2 -178.9(4) . . . . ?
C4 C5 C6 C7 -0.6(6) . . . . ?
N2 C6 C7 C8 178.8(4) . . . . ?
C5 C6 C7 C8 0.5(6) . . . . ?
C6 C7 C8 C3 0.1(6) . . . . ?
C4 C3 C8 C7 -0.7(6) . . . . ?
C2 C3 C8 C7 178.5(3) . . . . ?
C6 N2 C9 C10 -80.4(5) . . . . ?
C11A N2 C9 C10 105.3(5) . . . . ?
C11B N2 C9 C10 65.4(6) . . . . ?
C6 N2 C11A C12A 89.1(7) . . . . ?
C9 N2 C11A C12A -96.6(6) . . . . ?
C6 N2 C11B C12B -112.3(7) . . . . ?
C9 N2 C11B C12B 99.7(7) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O1 H1 N1 0.83 1.85 2.606(4) 150.6 . yes

_refine_diff_density_max         0.896
_refine_diff_density_min         -0.791
_refine_diff_density_rms         0.084























####################################################################### 
# 
# 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_SPA447
_database_code_depnum_ccdc_archive 'CCDC 2073011'
loop_
_audit_author_name
_audit_author_address
'Vedichi Madhu'
;Department of Chemistry, Karunya University
India
;
_audit_update_record             
;
2021-03-25 deposited with the CCDC.	2021-08-30 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         'C24 H30 N4 O2 S'
_chemical_formula_sum            'C24 H30 N4 O2 S'
_chemical_formula_weight         438.58

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0019 0.0011 '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 0.0040 0.0024 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0074 0.0043 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.0966 0.0914 '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                   6.6330(13)
_cell_length_b                   8.5300(17)
_cell_length_c                   19.929(4)
_cell_angle_alpha                90
_cell_angle_beta                 94.24(3)
_cell_angle_gamma                90
_cell_volume                     1124.5(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    220(2)
_cell_measurement_reflns_used    34490
_cell_measurement_theta_min      0.350
_cell_measurement_theta_max      33.679

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.295
_exptl_crystal_F_000             468
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.135
_exptl_crystal_size_mid          0.094
_exptl_crystal_size_min          0.084
_exptl_absorpt_coefficient_mu    0.117
_shelx_estimated_absorpt_T_min   0.984
_shelx_estimated_absorpt_T_max   0.990
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.849
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
'HKL3000sm Scalepack(Otwinowski et.al,2003)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      220(2)
_diffrn_radiation_wavelength     0.610
_diffrn_radiation_type           synchrotron
_diffrn_source                   'PLSII 2D bending magnet'
_diffrn_measurement_device_type  'Rayonix MX225HS CCD area detector'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11469
_diffrn_reflns_av_unetI/netI     0.0488
_diffrn_reflns_av_R_equivalents  0.0420
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         1.759
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_full        21.469
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measured_fraction_theta_full 0.976
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_Laue_measured_fraction_full 0.976
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_point_group_measured_fraction_full 0.972
_reflns_number_total             6002
_reflns_number_gt                5452
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.869
_reflns_Friedel_fraction_max     0.956
_reflns_Friedel_fraction_full    0.967

_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       
'PAL BL2D-SMDC Program(Shin et.al, 2016)'
_computing_cell_refinement       'HKL3000sm(Otwinowski & Minor, 1997)'
_computing_data_reduction        'HKL3000sm(Otwinowski & Minor, 1997)'
_computing_structure_solution    'SHELXT-2018(Sheldrick, 2015a)'
_computing_structure_refinement  'SHELXL-2018(Sheldrick, 2015b)'
_computing_molecular_graphics    'DIAMOND 4(Putz&Brandenburg, 2014)'
_computing_publication_material  'publCIF(Westrip, 2010)'
_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)+(0.1001P)²+0.1152P] 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 2191 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.06(3)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         6002
_refine_ls_number_parameters     286
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0583
_refine_ls_R_factor_gt           0.0545
_refine_ls_wR_factor_ref         0.1585
_refine_ls_wR_factor_gt          0.1556
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_restrained_S_all      1.051
_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
S1 S 0.54797(11) 0.48263(10) 0.70822(4) 0.0406(2) Uani 1 1 d . . . . .
O1 O -0.0142(4) 0.6106(4) 0.81943(12) 0.0513(6) Uani 1 1 d . . . . .
H1 H 0.007571 0.620556 0.779176 0.077 Uiso 1 1 calc R U . . .
O2 O 0.5335(4) 0.7234(4) 0.45608(13) 0.0500(6) Uani 1 1 d . . . . .
H2 H 0.494827 0.713031 0.494499 0.075 Uiso 1 1 calc R U . . .
N1 N 0.2068(4) 0.6230(4) 0.71555(14) 0.0468(7) Uani 1 1 d . . . . .
N2 N 0.5338(4) 0.6023(4) 0.57749(14) 0.0433(6) Uani 1 1 d . . . . .
N3 N 0.2342(4) 0.3589(4) 1.02200(14) 0.0388(5) Uani 1 1 d . . . . .
N4 N 1.0913(4) 0.6170(4) 0.32753(14) 0.0415(6) Uani 1 1 d . . . . .
C1 C 0.3425(4) 0.5392(4) 0.75156(16) 0.0381(6) Uani 1 1 d . . . . .
C2 C 0.3185(4) 0.4934(4) 0.82097(14) 0.0378(6) Uani 1 1 d . . . . .
C3 C 0.1398(5) 0.5318(4) 0.85179(16) 0.0400(7) Uani 1 1 d . . . . .
C4 C 0.1158(4) 0.4882(5) 0.91830(15) 0.0392(6) Uani 1 1 d . . . . .
H4 H -0.004494 0.515106 0.937633 0.047 Uiso 1 1 calc R U . . .
C5 C 0.2650(4) 0.4057(4) 0.95709(15) 0.0355(6) Uani 1 1 d . . . . .
C6 C 0.4443(5) 0.3679(4) 0.92607(16) 0.0399(6) Uani 1 1 d . . . . .
H6 H 0.548238 0.312391 0.950303 0.048 Uiso 1 1 calc R U . . .
C7 C 0.4670(5) 0.4122(4) 0.86050(17) 0.0401(6) Uani 1 1 d . . . . .
H7 H 0.588278 0.386639 0.841453 0.048 Uiso 1 1 calc R U . . .
C8 C 0.0604(5) 0.4172(4) 1.05514(16) 0.0408(7) Uani 1 1 d . . . . .
H8A H 0.043635 0.353192 1.095178 0.049 Uiso 1 1 calc R U . . .
H8AB H -0.061061 0.403706 1.024603 0.049 Uiso 1 1 calc R U . . .
C9 C 0.0760(6) 0.5882(5) 1.07615(19) 0.0478(8) Uani 1 1 d . . . . .
H9A H -0.045521 0.618507 1.097124 0.072 Uiso 1 1 calc R U . . .
H9B H 0.090822 0.652975 1.036827 0.072 Uiso 1 1 calc R U . . .
H9C H 0.192554 0.602229 1.107928 0.072 Uiso 1 1 calc R U . . .
C10 C 0.3899(5) 0.2779(5) 1.06415(18) 0.0458(7) Uani 1 1 d . . . . .
H10A H 0.462342 0.206342 1.035920 0.055 Uiso 1 1 calc R U . . .
H10B H 0.324568 0.214427 1.097325 0.055 Uiso 1 1 calc R U . . .
C11 C 0.5417(6) 0.3862(6) 1.1010(2) 0.0577(10) Uani 1 1 d . . . . .
H11A H 0.644221 0.324275 1.126041 0.087 Uiso 1 1 calc R U . . .
H11B H 0.473035 0.452029 1.131770 0.087 Uiso 1 1 calc R U . . .
H11C H 0.604898 0.451510 1.068670 0.087 Uiso 1 1 calc R U . . .
C12 C 0.7011(5) 0.5342(4) 0.56693(17) 0.0445(7) Uani 1 1 d . . . . .
H12 H 0.763166 0.469969 0.600768 0.053 Uiso 1 1 calc R U . . .
C13 C 0.7961(5) 0.5531(4) 0.50525(16) 0.0418(7) Uani 1 1 d . . . . .
C14 C 0.7109(4) 0.6472(4) 0.45202(15) 0.0369(6) Uani 1 1 d . . . . .
C15 C 0.8066(4) 0.6656(4) 0.39311(15) 0.0374(6) Uani 1 1 d . . . . .
H15 H 0.745859 0.727118 0.358074 0.045 Uiso 1 1 calc R U . . .
C16 C 0.9950(4) 0.5928(4) 0.38509(15) 0.0377(6) Uani 1 1 d . . . . .
C17 C 1.0786(5) 0.4968(5) 0.43783(18) 0.0497(8) Uani 1 1 d . . . . .
H17 H 1.201358 0.444332 0.433169 0.060 Uiso 1 1 calc R U . . .
C18 C 0.9822(5) 0.4800(6) 0.49535(17) 0.0501(8) Uani 1 1 d . . . . .
H18 H 1.042298 0.417008 0.529976 0.060 Uiso 1 1 calc R U . . .
C19 C 0.9865(5) 0.6916(5) 0.26903(18) 0.0459(7) Uani 1 1 d . . . . .
H19A H 1.085498 0.717493 0.236607 0.055 Uiso 1 1 calc R U . . .
H19B H 0.926424 0.789966 0.283240 0.055 Uiso 1 1 calc R U . . .
C20 C 0.8214(5) 0.5906(5) 0.23425(18) 0.0507(8) Uani 1 1 d . . . . .
H20A H 0.758111 0.646936 0.196003 0.076 Uiso 1 1 calc R U . . .
H20B H 0.720808 0.566436 0.265632 0.076 Uiso 1 1 calc R U . . .
H20C H 0.879995 0.494008 0.218909 0.076 Uiso 1 1 calc R U . . .
C21 C 1.2881(5) 0.5465(5) 0.31691(19) 0.0475(8) Uani 1 1 d . . . . .
H21A H 1.364115 0.534661 0.360681 0.057 Uiso 1 1 calc R U . . .
H21B H 1.363796 0.618764 0.289972 0.057 Uiso 1 1 calc R U . . .
C22 C 1.2776(6) 0.3902(5) 0.2826(3) 0.0590(10) Uani 1 1 d . . . . .
H22A H 1.412718 0.347157 0.281705 0.088 Uiso 1 1 calc R U . . .
H22B H 1.218591 0.402616 0.236899 0.088 Uiso 1 1 calc R U . . .
H22C H 1.194618 0.319563 0.306952 0.088 Uiso 1 1 calc R U . . .
C23 C 0.4424(5) 0.5848(4) 0.63808(16) 0.0411(7) Uani 1 1 d . . . . .
C24 C 0.2654(5) 0.6499(5) 0.65215(17) 0.0489(8) Uani 1 1 d . . . . .
H24 H 0.187055 0.710002 0.620436 0.059 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
S1 C1 1.735(3) . ?
S1 C23 1.749(3) . ?
O1 C3 1.347(4) . ?
O1 H1 0.8300 . ?
O2 C14 1.352(4) . ?
O2 H2 0.8300 . ?
N1 C1 1.319(4) . ?
N1 C24 1.368(5) . ?
N2 C12 1.283(5) . ?
N2 C23 1.399(4) . ?
N3 C5 1.383(4) . ?
N3 C10 1.456(4) . ?
N3 C8 1.458(4) . ?
N4 C16 1.369(4) . ?
N4 C19 1.458(4) . ?
N4 C21 1.467(4) . ?
C1 C2 1.458(4) . ?
C2 C7 1.398(4) . ?
C2 C3 1.413(4) . ?
C3 C4 1.397(4) . ?
C4 C5 1.400(4) . ?
C4 H4 0.9400 . ?
C5 C6 1.417(4) . ?
C6 C7 1.379(5) . ?
C6 H6 0.9400 . ?
C7 H7 0.9400 . ?
C8 C9 1.519(5) . ?
C8 H8A 0.9800 . ?
C8 H8AB 0.9800 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 H9C 0.9700 . ?
C10 C11 1.515(6) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 H11C 0.9700 . ?
C12 C13 1.431(5) . ?
C12 H12 0.9400 . ?
C13 C18 1.410(5) . ?
C13 C14 1.414(4) . ?
C14 C15 1.385(4) . ?
C15 C16 1.415(4) . ?
C15 H15 0.9400 . ?
C16 C17 1.413(5) . ?
C17 C18 1.361(5) . ?
C17 H17 0.9400 . ?
C18 H18 0.9400 . ?
C19 C20 1.519(5) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C20 H20C 0.9700 . ?
C21 C22 1.498(6) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C22 H22C 0.9700 . ?
C23 C24 1.347(5) . ?
C24 H24 0.9400 . ?

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
C1 S1 C23 88.64(16) . . ?
C3 O1 H1 109.5 . . ?
C14 O2 H2 109.5 . . ?
C1 N1 C24 111.4(3) . . ?
C12 N2 C23 121.9(3) . . ?
C5 N3 C10 121.9(3) . . ?
C5 N3 C8 120.1(3) . . ?
C10 N3 C8 116.8(3) . . ?
C16 N4 C19 120.7(3) . . ?
C16 N4 C21 122.3(3) . . ?
C19 N4 C21 116.1(3) . . ?
N1 C1 C2 122.9(3) . . ?
N1 C1 S1 114.2(2) . . ?
C2 C1 S1 122.9(2) . . ?
C7 C2 C3 116.7(3) . . ?
C7 C2 C1 123.1(3) . . ?
C3 C2 C1 120.3(3) . . ?
O1 C3 C4 116.8(3) . . ?
O1 C3 C2 122.6(3) . . ?
C4 C3 C2 120.6(3) . . ?
C3 C4 C5 122.2(3) . . ?
C3 C4 H4 118.9 . . ?
C5 C4 H4 118.9 . . ?
N3 C5 C4 120.9(3) . . ?
N3 C5 C6 121.9(3) . . ?
C4 C5 C6 117.1(3) . . ?
C7 C6 C5 120.3(3) . . ?
C7 C6 H6 119.8 . . ?
C5 C6 H6 119.8 . . ?
C6 C7 C2 123.2(3) . . ?
C6 C7 H7 118.4 . . ?
C2 C7 H7 118.4 . . ?
N3 C8 C9 114.4(3) . . ?
N3 C8 H8A 108.7 . . ?
C9 C8 H8A 108.7 . . ?
N3 C8 H8AB 108.7 . . ?
C9 C8 H8AB 108.7 . . ?
H8A C8 H8AB 107.6 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N3 C10 C11 114.1(3) . . ?
N3 C10 H10A 108.7 . . ?
C11 C10 H10A 108.7 . . ?
N3 C10 H10B 108.7 . . ?
C11 C10 H10B 108.7 . . ?
H10A C10 H10B 107.6 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N2 C12 C13 122.1(3) . . ?
N2 C12 H12 119.0 . . ?
C13 C12 H12 119.0 . . ?
C18 C13 C14 116.8(3) . . ?
C18 C13 C12 121.1(3) . . ?
C14 C13 C12 122.1(3) . . ?
O2 C14 C15 116.9(3) . . ?
O2 C14 C13 122.0(3) . . ?
C15 C14 C13 121.2(3) . . ?
C14 C15 C16 120.7(3) . . ?
C14 C15 H15 119.7 . . ?
C16 C15 H15 119.7 . . ?
N4 C16 C17 121.9(3) . . ?
N4 C16 C15 119.9(3) . . ?
C17 C16 C15 118.1(3) . . ?
C18 C17 C16 120.3(3) . . ?
C18 C17 H17 119.8 . . ?
C16 C17 H17 119.8 . . ?
C17 C18 C13 122.8(3) . . ?
C17 C18 H18 118.6 . . ?
C13 C18 H18 118.6 . . ?
N4 C19 C20 113.7(3) . . ?
N4 C19 H19A 108.8 . . ?
C20 C19 H19A 108.8 . . ?
N4 C19 H19B 108.8 . . ?
C20 C19 H19B 108.8 . . ?
H19A C19 H19B 107.7 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
N4 C21 C22 114.8(3) . . ?
N4 C21 H21A 108.6 . . ?
C22 C21 H21A 108.6 . . ?
N4 C21 H21B 108.6 . . ?
C22 C21 H21B 108.6 . . ?
H21A C21 H21B 107.5 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C24 C23 N2 125.2(3) . . ?
C24 C23 S1 110.1(3) . . ?
N2 C23 S1 124.7(3) . . ?
C23 C24 N1 115.8(3) . . ?
C23 C24 H24 122.1 . . ?
N1 C24 H24 122.1 . . ?

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
C24 N1 C1 C2 -180.0(3) . . . . ?
C24 N1 C1 S1 -2.0(4) . . . . ?
C23 S1 C1 N1 1.6(3) . . . . ?
C23 S1 C1 C2 179.5(3) . . . . ?
N1 C1 C2 C7 -176.3(3) . . . . ?
S1 C1 C2 C7 6.0(5) . . . . ?
N1 C1 C2 C3 3.2(5) . . . . ?
S1 C1 C2 C3 -174.6(3) . . . . ?
C7 C2 C3 O1 179.6(3) . . . . ?
C1 C2 C3 O1 0.1(5) . . . . ?
C7 C2 C3 C4 -0.6(5) . . . . ?
C1 C2 C3 C4 180.0(3) . . . . ?
O1 C3 C4 C5 179.9(3) . . . . ?
C2 C3 C4 C5 0.0(6) . . . . ?
C10 N3 C5 C4 -177.8(3) . . . . ?
C8 N3 C5 C4 -10.4(5) . . . . ?
C10 N3 C5 C6 4.6(5) . . . . ?
C8 N3 C5 C6 172.0(3) . . . . ?
C3 C4 C5 N3 -177.6(3) . . . . ?
C3 C4 C5 C6 0.2(5) . . . . ?
N3 C5 C6 C7 177.9(3) . . . . ?
C4 C5 C6 C7 0.1(5) . . . . ?
C5 C6 C7 C2 -0.8(6) . . . . ?
C3 C2 C7 C6 1.0(5) . . . . ?
C1 C2 C7 C6 -179.6(3) . . . . ?
C5 N3 C8 C9 -72.4(4) . . . . ?
C10 N3 C8 C9 95.6(4) . . . . ?
C5 N3 C10 C11 84.3(4) . . . . ?
C8 N3 C10 C11 -83.5(4) . . . . ?
C23 N2 C12 C13 -179.4(3) . . . . ?
N2 C12 C13 C18 178.5(4) . . . . ?
N2 C12 C13 C14 -0.4(6) . . . . ?
C18 C13 C14 O2 -179.7(4) . . . . ?
C12 C13 C14 O2 -0.7(5) . . . . ?
C18 C13 C14 C15 0.1(5) . . . . ?
C12 C13 C14 C15 179.1(3) . . . . ?
O2 C14 C15 C16 178.6(3) . . . . ?
C13 C14 C15 C16 -1.2(5) . . . . ?
C19 N4 C16 C17 168.4(3) . . . . ?
C21 N4 C16 C17 -0.6(5) . . . . ?
C19 N4 C16 C15 -11.9(5) . . . . ?
C21 N4 C16 C15 179.1(3) . . . . ?
C14 C15 C16 N4 -177.5(3) . . . . ?
C14 C15 C16 C17 2.1(5) . . . . ?
N4 C16 C17 C18 177.6(4) . . . . ?
C15 C16 C17 C18 -2.1(6) . . . . ?
C16 C17 C18 C13 1.1(7) . . . . ?
C14 C13 C18 C17 -0.1(6) . . . . ?
C12 C13 C18 C17 -179.1(4) . . . . ?
C16 N4 C19 C20 -69.6(4) . . . . ?
C21 N4 C19 C20 100.0(4) . . . . ?
C16 N4 C21 C22 91.1(4) . . . . ?
C19 N4 C21 C22 -78.3(4) . . . . ?
C12 N2 C23 C24 -178.6(4) . . . . ?
C12 N2 C23 S1 4.7(5) . . . . ?
C1 S1 C23 C24 -0.6(3) . . . . ?
C1 S1 C23 N2 176.5(3) . . . . ?
N2 C23 C24 N1 -177.5(3) . . . . ?
S1 C23 C24 N1 -0.3(5) . . . . ?
C1 N1 C24 C23 1.5(5) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O1 H1 N1 0.83 1.90 2.626(4) 145.8 . yes
O2 H2 N2 0.83 1.91 2.631(4) 145.3 . yes

_refine_diff_density_max         0.982
_refine_diff_density_min         -0.459
_refine_diff_density_rms         0.058























