# Electronic Supplementary Material (ESI) for ChemComm.
# 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_YS-CHO
_database_code_depnum_ccdc_archive 'CCDC 1847224'
loop_
_audit_author_name
_audit_author_address
'Jae Kyun Lee'
;Korea Institute of Science and Technology
South Korea
;
_audit_update_record             
;
2018-06-05 deposited with the CCDC.	2022-11-30 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C16 H18 N2 O2'
_chemical_formula_moiety         'C16 H18 N2 O2'
_chemical_formula_weight         270.33
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
_space_group_IT_number           14
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,1/2+Y,1/2-Z
3 -X,-Y,-Z
4 +X,-1/2-Y,-1/2+Z
#------------------------------------------------------------------------------
_cell_length_a                   10.3324(8)
_cell_length_b                   10.1087(6)
_cell_length_c                   13.8942(10)
_cell_angle_alpha                90.0000
_cell_angle_beta                 109.438(3)
_cell_angle_gamma                90.0000
_cell_volume                     1368.49(17)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8687
_cell_measurement_theta_min      2.99
_cell_measurement_theta_max      27.43
_cell_measurement_temperature    296
#------------------------------------------------------------------------------
_exptl_crystal_description       chunk
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_crystal_density_diffrn    1.312
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             576.00
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_absorpt_correction_T_min  0.762
_exptl_absorpt_correction_T_max  0.983

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      296
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.000
_diffrn_reflns_number            12866
_diffrn_reflns_av_R_equivalents  0.0298
_diffrn_reflns_theta_max         27.450
_diffrn_reflns_theta_min         3.117
_diffrn_reflns_theta_full        27.450
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.000
_diffrn_reflns_Laue_measured_fraction_full 0.000
_diffrn_reflns_point_group_measured_fraction_max 0.000
_diffrn_reflns_point_group_measured_fraction_full 0.000
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             3115
_reflns_number_gt                1981
_reflns_threshold_expression     F²>2.0σ(F²)

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0698
_refine_ls_R_factor_gt           0.0400
_refine_ls_wR_factor_ref         0.1359
_refine_ls_wR_factor_gt          0.1188
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_reflns         6595
_refine_ls_number_parameters     205
_refine_ls_goodness_of_fit_ref   1.145
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0731P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.19
_refine_diff_density_min         -0.20
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0106 0.0060
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.27834(14) 0.03616(12) 0.64344(9) 0.0593(4) Uani 1 1 d . . .
O18 O 0.19341(16) -0.09088(12) 0.09421(9) 0.0712(4) Uani 1 1 d . . .
N1 N 0.20096(13) 0.07119(11) 0.21075(9) 0.0372(3) Uani 1 1 d . . .
N19 N 0.22012(14) 0.12374(11) 0.48149(9) 0.0385(3) Uani 1 1 d . . .
C2 C 0.26812(16) 0.10122(13) 0.31953(11) 0.0355(4) Uani 1 1 d . . .
C3 C 0.16156(16) 0.08025(13) 0.37608(10) 0.0341(3) Uani 1 1 d . . .
C4 C 0.02708(17) 0.15481(15) 0.32037(11) 0.0413(4) Uani 1 1 d . . .
H4A H -0.0407 0.1336 0.3523 0.050 Uiso 1 1 calc R . .
H4B H 0.0440 0.2493 0.3272 0.050 Uiso 1 1 calc R . .
C5 C -0.02922(16) 0.11953(14) 0.20872(11) 0.0392(4) Uani 1 1 d . . .
C6 C 0.23004(17) 0.02519(15) 0.55013(11) 0.0412(4) Uani 1 1 d . . .
C7 C 0.07189(16) 0.13624(15) 0.15262(11) 0.0415(4) Uani 1 1 d . . .
H7A H 0.0354 0.0972 0.0852 0.050 Uiso 1 1 calc R . .
H7B H 0.0879 0.2296 0.1448 0.050 Uiso 1 1 calc R . .
C8 C 0.24414(19) -0.04222(16) 0.17918(12) 0.0480(4) Uani 1 1 d . . .
C9 C 0.13307(18) -0.06307(15) 0.39017(12) 0.0438(4) Uani 1 1 d . . .
C10 C 0.32033(18) 0.24497(15) 0.33590(12) 0.0443(4) Uani 1 1 d . . .
H10A H 0.3904 0.2572 0.3044 0.053 Uiso 1 1 calc R . .
H10B H 0.2451 0.3047 0.3030 0.053 Uiso 1 1 calc R . .
C11 C -0.1554(2) 0.07556(17) 0.16333(15) 0.0496(4) Uani 1 1 d . . .
C12 C 0.37885(18) 0.27837(14) 0.44729(12) 0.0462(4) Uani 1 1 d . . .
C13 C 0.38781(19) 0.00254(16) 0.35112(13) 0.0490(4) Uani 1 1 d . . .
H13A H 0.4740 0.0478 0.3609 0.059 Uiso 1 1 calc R . .
H13B H 0.3927 -0.0410 0.4144 0.059 Uiso 1 1 calc R . .
C14 C 0.17258(19) -0.09495(15) 0.48875(13) 0.0462(4) Uani 1 1 d . . .
C15 C 0.28244(19) 0.25420(15) 0.50630(12) 0.0482(4) Uani 1 1 d . . .
H15A H 0.3324 0.2596 0.5789 0.058 Uiso 1 1 calc R . .
H15B H 0.2114 0.3214 0.4893 0.058 Uiso 1 1 calc R . .
C16 C 0.3608(2) -0.09636(19) 0.26668(13) 0.0637(5) Uani 1 1 d . . .
H16A H 0.3362 -0.1813 0.2882 0.076 Uiso 1 1 calc R . .
H16B H 0.4417 -0.1079 0.2469 0.076 Uiso 1 1 calc R . .
C17 C 0.5039(2) 0.3251(2) 0.49158(17) 0.0657(6) Uani 1 1 d . . .
H11A H -0.2185(19) 0.0626(18) 0.1967(14) 0.054(5) Uiso 1 1 d . . .
H11B H -0.200(2) 0.0558(18) 0.0879(15) 0.059(5) Uiso 1 1 d . . .
H17A H 0.564(3) 0.340(2) 0.4524(18) 0.099(8) Uiso 1 1 d . . .
H17B H 0.541(2) 0.346(2) 0.5693(16) 0.075(6) Uiso 1 1 d . . .
H20 H 0.1645(18) -0.1772(18) 0.5175(12) 0.051(5) Uiso 1 1 d . . .
H21 H 0.1007(16) -0.1194(15) 0.3340(12) 0.042(4) Uiso 1 1 d . . .


#==============================================================================
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_cell_refinement       'RAPID AUTO'
_computing_data_reduction        'RAPID AUTO'
_computing_structure_solution    'Il Milione (Burla, et al., 2007)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.2 (Rigaku, 2017)'
_computing_molecular_graphics    'CrystalStructure 4.2'

#==============================================================================
# MOLECULAR GEOMETRY

_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
O1 C6 1.2295(18) . ?
O18 C8 1.2242(19) . ?
N1 C8 1.355(2) . ?
N1 C7 1.4651(19) . ?
N1 C2 1.4697(18) . ?
N19 C6 1.3592(19) . ?
N19 C3 1.4541(17) . ?
N19 C15 1.4577(19) . ?
C2 C13 1.535(2) . ?
C2 C10 1.540(2) . ?
C2 C3 1.565(2) . ?
C3 C9 1.5041(19) . ?
C3 C4 1.543(2) . ?
C4 C5 1.507(2) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C11 1.322(2) . ?
C5 C7 1.506(2) . ?
C6 C14 1.489(2) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C16 1.502(2) . ?
C9 C14 1.332(2) . ?
C9 H21 0.933(16) . ?
C10 C12 1.501(2) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 H11A 0.927(19) . ?
C11 H11B 1.015(19) . ?
C12 C17 1.321(3) . ?
C12 C15 1.506(2) . ?
C13 C16 1.495(2) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 H20 0.938(18) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 H17A 0.96(3) . ?
C17 H17B 1.04(2) . ?

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 122.59(13) . . ?
C8 N1 C2 114.46(12) . . ?
C7 N1 C2 120.39(11) . . ?
C6 N19 C3 113.21(11) . . ?
C6 N19 C15 124.95(13) . . ?
C3 N19 C15 120.98(11) . . ?
N1 C2 C13 102.68(11) . . ?
N1 C2 C10 111.65(11) . . ?
C13 C2 C10 111.20(14) . . ?
N1 C2 C3 108.54(12) . . ?
C13 C2 C3 113.76(12) . . ?
C10 C2 C3 108.90(12) . . ?
N19 C3 C9 101.19(11) . . ?
N19 C3 C4 111.15(12) . . ?
C9 C3 C4 110.68(13) . . ?
N19 C3 C2 109.77(12) . . ?
C9 C3 C2 113.36(12) . . ?
C4 C3 C2 110.39(11) . . ?
C5 C4 C3 112.04(12) . . ?
C5 C4 H4A 109.2 . . ?
C3 C4 H4A 109.2 . . ?
C5 C4 H4B 109.2 . . ?
C3 C4 H4B 109.2 . . ?
H4A C4 H4B 107.9 . . ?
C11 C5 C7 122.30(15) . . ?
C11 C5 C4 123.52(16) . . ?
C7 C5 C4 114.17(13) . . ?
O1 C6 N19 125.68(14) . . ?
O1 C6 C14 128.46(14) . . ?
N19 C6 C14 105.86(13) . . ?
N1 C7 C5 108.98(12) . . ?
N1 C7 H7A 109.9 . . ?
C5 C7 H7A 109.9 . . ?
N1 C7 H7B 109.9 . . ?
C5 C7 H7B 109.9 . . ?
H7A C7 H7B 108.3 . . ?
O18 C8 N1 124.80(16) . . ?
O18 C8 C16 127.22(15) . . ?
N1 C8 C16 107.96(13) . . ?
C14 C9 C3 111.13(13) . . ?
C14 C9 H21 127.9(10) . . ?
C3 C9 H21 120.7(10) . . ?
C12 C10 C2 111.44(12) . . ?
C12 C10 H10A 109.3 . . ?
C2 C10 H10A 109.3 . . ?
C12 C10 H10B 109.3 . . ?
C2 C10 H10B 109.3 . . ?
H10A C10 H10B 108.0 . . ?
C5 C11 H11A 123.7(11) . . ?
C5 C11 H11B 126.5(11) . . ?
H11A C11 H11B 109.7(16) . . ?
C17 C12 C10 123.86(18) . . ?
C17 C12 C15 121.77(17) . . ?
C10 C12 C15 114.37(14) . . ?
C16 C13 C2 106.75(13) . . ?
C16 C13 H13A 110.4 . . ?
C2 C13 H13A 110.4 . . ?
C16 C13 H13B 110.4 . . ?
C2 C13 H13B 110.4 . . ?
H13A C13 H13B 108.6 . . ?
C9 C14 C6 108.60(13) . . ?
C9 C14 H20 127.7(10) . . ?
C6 C14 H20 123.6(10) . . ?
N19 C15 C12 109.77(12) . . ?
N19 C15 H15A 109.7 . . ?
C12 C15 H15A 109.7 . . ?
N19 C15 H15B 109.7 . . ?
C12 C15 H15B 109.7 . . ?
H15A C15 H15B 108.2 . . ?
C13 C16 C8 106.34(14) . . ?
C13 C16 H16A 110.5 . . ?
C8 C16 H16A 110.5 . . ?
C13 C16 H16B 110.5 . . ?
C8 C16 H16B 110.5 . . ?
H16A C16 H16B 108.7 . . ?
C12 C17 H17A 120.4(15) . . ?
C12 C17 H17B 121.2(12) . . ?
H17A C17 H17B 118(2) . . ?

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
C8 N1 C2 C13 11.89(17) . . . . ?
C7 N1 C2 C13 174.22(13) . . . . ?
C8 N1 C2 C10 131.11(15) . . . . ?
C7 N1 C2 C10 -66.56(17) . . . . ?
C8 N1 C2 C3 -108.84(15) . . . . ?
C7 N1 C2 C3 53.48(16) . . . . ?
C6 N19 C3 C9 1.24(16) . . . . ?
C15 N19 C3 C9 171.11(15) . . . . ?
C6 N19 C3 C4 118.78(14) . . . . ?
C15 N19 C3 C4 -71.34(18) . . . . ?
C6 N19 C3 C2 -118.80(13) . . . . ?
C15 N19 C3 C2 51.07(18) . . . . ?
N1 C2 C3 N19 -173.49(10) . . . . ?
C13 C2 C3 N19 72.89(15) . . . . ?
C10 C2 C3 N19 -51.74(15) . . . . ?
N1 C2 C3 C9 74.19(14) . . . . ?
C13 C2 C3 C9 -39.43(17) . . . . ?
C10 C2 C3 C9 -164.06(13) . . . . ?
N1 C2 C3 C4 -50.62(14) . . . . ?
C13 C2 C3 C4 -164.24(12) . . . . ?
C10 C2 C3 C4 71.13(15) . . . . ?
N19 C3 C4 C5 175.26(12) . . . . ?
C9 C3 C4 C5 -73.12(16) . . . . ?
C2 C3 C4 C5 53.21(16) . . . . ?
C3 C4 C5 C11 125.44(16) . . . . ?
C3 C4 C5 C7 -53.50(16) . . . . ?
C3 N19 C6 O1 178.51(16) . . . . ?
C15 N19 C6 O1 9.1(3) . . . . ?
C3 N19 C6 C14 -0.92(18) . . . . ?
C15 N19 C6 C14 -170.32(15) . . . . ?
C8 N1 C7 C5 108.83(16) . . . . ?
C2 N1 C7 C5 -52.02(17) . . . . ?
C11 C5 C7 N1 -129.69(15) . . . . ?
C4 C5 C7 N1 49.26(16) . . . . ?
C7 N1 C8 O18 11.5(3) . . . . ?
C2 N1 C8 O18 173.43(17) . . . . ?
C7 N1 C8 C16 -167.34(15) . . . . ?
C2 N1 C8 C16 -5.5(2) . . . . ?
N19 C3 C9 C14 -1.12(17) . . . . ?
C4 C3 C9 C14 -119.01(15) . . . . ?
C2 C3 C9 C14 116.33(16) . . . . ?
N1 C2 C10 C12 175.53(13) . . . . ?
C13 C2 C10 C12 -70.43(17) . . . . ?
C3 C2 C10 C12 55.69(17) . . . . ?
C2 C10 C12 C17 125.00(18) . . . . ?
C2 C10 C12 C15 -55.02(19) . . . . ?
N1 C2 C13 C16 -13.30(18) . . . . ?
C10 C2 C13 C16 -132.84(15) . . . . ?
C3 C2 C13 C16 103.77(16) . . . . ?
C3 C9 C14 C6 0.6(2) . . . . ?
O1 C6 C14 C9 -179.26(17) . . . . ?
N19 C6 C14 C9 0.15(19) . . . . ?
C6 N19 C15 C12 121.07(16) . . . . ?
C3 N19 C15 C12 -47.6(2) . . . . ?
C17 C12 C15 N19 -132.74(17) . . . . ?
C10 C12 C15 N19 47.28(19) . . . . ?
C2 C13 C16 C8 10.8(2) . . . . ?
O18 C8 C16 C13 177.42(19) . . . . ?
N1 C8 C16 C13 -3.7(2) . . . . ?
####################################################################### 
# 
# 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_KT1025
_database_code_depnum_ccdc_archive 'CCDC 2220271'
loop_
_audit_author_name
_audit_author_address
'Jae Kyun Lee'
;Korea Institute of Science and Technology
South Korea
;
_audit_update_record             
;
2022-11-17 deposited with the CCDC.	2022-11-30 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C27 H28 N2 O3 S'
_chemical_formula_moiety         'C27 H28 N2 O3 S'
_chemical_formula_weight         460.59
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
_space_group_IT_number           14
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,1/2+Y,1/2-Z
3 -X,-Y,-Z
4 +X,-1/2-Y,-1/2+Z
#------------------------------------------------------------------------------
_cell_length_a                   18.6366(8)
_cell_length_b                   12.5881(8)
_cell_length_c                   10.2431(5)
_cell_angle_alpha                90.0000
_cell_angle_beta                 94.9576(12)
_cell_angle_gamma                90.0000
_cell_volume                     2394.0(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    15669
_cell_measurement_theta_min      3.23
_cell_measurement_theta_max      27.46
_cell_measurement_temperature    296
#------------------------------------------------------------------------------
_exptl_crystal_description       chunk
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.300
_exptl_crystal_density_diffrn    1.278
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             976.00
_exptl_absorpt_coefficient_mu    0.166
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_absorpt_correction_T_min  0.722
_exptl_absorpt_correction_T_max  0.951

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      296
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.000
_diffrn_reflns_number            23098
_diffrn_reflns_av_R_equivalents  0.0329
_diffrn_reflns_theta_max         27.470
_diffrn_reflns_theta_min         3.237
_diffrn_reflns_theta_full        27.470
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.000
_diffrn_reflns_Laue_measured_fraction_full 0.000
_diffrn_reflns_point_group_measured_fraction_max 0.000
_diffrn_reflns_point_group_measured_fraction_full 0.000
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             5467
_reflns_number_gt                3724
_reflns_threshold_expression     F²>2.0σ(F²)

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0680
_refine_ls_R_factor_gt           0.0421
_refine_ls_wR_factor_ref         0.1229
_refine_ls_wR_factor_gt          0.1087
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         5467
_refine_ls_number_parameters     300
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0548P)²+0.3518P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.003
_refine_diff_density_max         0.19
_refine_diff_density_min         -0.35
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0106 0.0060
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
S S 0.1246 0.1234
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.66242(2) 0.16264(4) 0.48218(4) 0.05039(14) Uani 1 1 d . . .
O1 O 0.84267(6) 0.07308(9) 1.00333(10) 0.0458(3) Uani 1 1 d . . .
O2 O 0.64469(7) 0.26895(10) 0.51618(15) 0.0656(4) Uani 1 1 d . . .
O3 O 0.65465(8) 0.13001(13) 0.34849(12) 0.0708(4) Uani 1 1 d . . .
N1 N 0.74761(7) 0.14622(11) 0.53538(13) 0.0454(3) Uani 1 1 d . . .
N2 N 0.83694(8) 0.02880(12) 0.59641(13) 0.0474(3) Uani 1 1 d . . .
C1 C 0.88963(9) 0.11949(14) 0.79703(15) 0.0432(4) Uani 1 1 d . . .
H1A H 0.9114 0.1768 0.7509 0.052 Uiso 1 1 calc R . .
H1B H 0.9236 0.0611 0.8055 0.052 Uiso 1 1 calc R . .
C2 C 0.87356(8) 0.15746(13) 0.93283(15) 0.0413(4) Uani 1 1 d . . .
H2 H 0.8387 0.2158 0.9226 0.050 Uiso 1 1 calc R . .
C3 C 0.78294(9) 0.00235(13) 0.80069(15) 0.0431(4) Uani 1 1 d . . .
H3A H 0.7355 -0.0123 0.7577 0.052 Uiso 1 1 calc R . .
H3B H 0.8101 -0.0635 0.8036 0.052 Uiso 1 1 calc R . .
C4 C 0.77470(9) 0.03885(13) 0.94095(16) 0.0422(4) Uani 1 1 d . . .
H4 H 0.7407 0.0983 0.9388 0.051 Uiso 1 1 calc R . .
C5 C 0.82074(8) 0.08321(13) 0.71864(15) 0.0406(4) Uani 1 1 d . . .
C6 C 0.77231(9) 0.17719(13) 0.67128(16) 0.0439(4) Uani 1 1 d . . .
H6A H 0.7320 0.1850 0.7245 0.053 Uiso 1 1 calc R . .
H6B H 0.7993 0.2431 0.6731 0.053 Uiso 1 1 calc R . .
C7 C 0.79332(9) 0.06023(14) 0.50270(16) 0.0475(4) Uani 1 1 d . . .
C8 C 0.79296(12) 0.01914(19) 0.36605(18) 0.0680(6) Uani 1 1 d . . .
H8A H 0.7499 -0.0215 0.3448 0.082 Uiso 1 1 calc R . .
H8B H 0.8343 -0.0253 0.3591 0.082 Uiso 1 1 calc R . .
H8C H 0.7944 0.0777 0.3063 0.082 Uiso 1 1 calc R . .
C9 C 0.74735(9) -0.04933(14) 1.02309(16) 0.0466(4) Uani 1 1 d . . .
C10 C 0.68146(10) -0.04114(16) 1.07433(18) 0.0566(5) Uani 1 1 d . . .
H10 H 0.6537 0.0197 1.0590 0.068 Uiso 1 1 calc R . .
C11 C 0.65647(12) -0.1235(2) 1.1488(2) 0.0756(7) Uani 1 1 d . . .
H11 H 0.6119 -0.1176 1.1827 0.091 Uiso 1 1 calc R . .
C12 C 0.69710(15) -0.2129(2) 1.1725(2) 0.0849(8) Uani 1 1 d . . .
H12 H 0.6804 -0.2674 1.2231 0.102 Uiso 1 1 calc R . .
C13 C 0.76302(15) -0.22229(18) 1.1211(2) 0.0804(7) Uani 1 1 d . . .
H13 H 0.7905 -0.2835 1.1363 0.097 Uiso 1 1 calc R . .
C14 C 0.78801(12) -0.14070(16) 1.0473(2) 0.0633(5) Uani 1 1 d . . .
H14 H 0.8325 -0.1470 1.0134 0.076 Uiso 1 1 calc R . .
C15 C 0.61371(9) 0.07646(13) 0.57602(17) 0.0462(4) Uani 1 1 d . . .
C16 C 0.59336(9) 0.11041(16) 0.69645(19) 0.0540(4) Uani 1 1 d . . .
H16 H 0.6021 0.1800 0.7238 0.065 Uiso 1 1 calc R . .
C17 C 0.56031(10) 0.04056(19) 0.7749(2) 0.0652(5) Uani 1 1 d . . .
H17 H 0.5471 0.0637 0.8557 0.078 Uiso 1 1 calc R . .
C18 C 0.54622(10) -0.0627(2) 0.7372(3) 0.0704(6) Uani 1 1 d . . .
C19 C 0.56455(11) -0.09424(16) 0.6153(3) 0.0740(7) Uani 1 1 d . . .
H19 H 0.5534 -0.1629 0.5866 0.089 Uiso 1 1 calc R . .
C20 C 0.59919(10) -0.02622(15) 0.5343(2) 0.0597(5) Uani 1 1 d . . .
H20 H 0.6124 -0.0494 0.4535 0.072 Uiso 1 1 calc R . .
C21 C 0.51204(15) -0.1401(3) 0.8262(3) 0.1164(12) Uani 1 1 d . . .
H21A H 0.4633 -0.1189 0.8357 0.140 Uiso 1 1 calc R . .
H21B H 0.5388 -0.1406 0.9106 0.140 Uiso 1 1 calc R . .
H21C H 0.5123 -0.2101 0.7888 0.140 Uiso 1 1 calc R . .
C22 C 0.94022(9) 0.19682(14) 1.01232(16) 0.0434(4) Uani 1 1 d . . .
C23 C 0.97610(9) 0.13705(15) 1.11101(18) 0.0520(4) Uani 1 1 d . . .
H23 H 0.9589 0.0701 1.1309 0.062 Uiso 1 1 calc R . .
C24 C 1.03779(10) 0.17678(18) 1.1806(2) 0.0603(5) Uani 1 1 d . . .
H24 H 1.0614 0.1368 1.2476 0.072 Uiso 1 1 calc R . .
C25 C 1.06378(10) 0.27461(19) 1.1506(2) 0.0666(6) Uani 1 1 d . . .
H25 H 1.1052 0.3008 1.1969 0.080 Uiso 1 1 calc R . .
C26 C 1.02888(11) 0.33448(18) 1.0521(2) 0.0663(6) Uani 1 1 d . . .
H26 H 1.0467 0.4008 1.0316 0.080 Uiso 1 1 calc R . .
C27 C 0.96745(10) 0.29581(16) 0.98410(18) 0.0545(5) Uani 1 1 d . . .
H27 H 0.9439 0.3368 0.9181 0.065 Uiso 1 1 calc R . .


#==============================================================================
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_cell_refinement       'RAPID AUTO'
_computing_data_reduction        'RAPID AUTO'
_computing_structure_solution    'Il Milione (Burla, et al., 2007)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.2 (Rigaku, 2017)'
_computing_molecular_graphics    'CrystalStructure 4.2'

#==============================================================================
# MOLECULAR GEOMETRY

_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 O3 1.4250(14) . ?
S1 O2 1.4288(14) . ?
S1 N1 1.6463(14) . ?
S1 C15 1.7538(18) . ?
O1 C2 1.4329(19) . ?
O1 C4 1.4348(19) . ?
N1 C7 1.435(2) . ?
N1 C6 1.480(2) . ?
N2 C7 1.267(2) . ?
N2 C5 1.4809(19) . ?
C1 C5 1.524(2) . ?
C1 C2 1.525(2) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 C22 1.509(2) . ?
C2 H2 0.9800 . ?
C3 C4 1.529(2) . ?
C3 C5 1.530(2) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C9 1.508(2) . ?
C4 H4 0.9800 . ?
C5 C6 1.541(2) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.492(2) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 C10 1.380(3) . ?
C9 C14 1.388(3) . ?
C10 C11 1.391(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.366(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.383(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.380(3) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C15 C20 1.381(2) . ?
C15 C16 1.389(3) . ?
C16 C17 1.373(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.375(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.381(3) . ?
C18 C21 1.513(3) . ?
C19 C20 1.389(3) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 C23 1.385(2) . ?
C22 C27 1.385(2) . ?
C23 C24 1.392(3) . ?
C23 H23 0.9300 . ?
C24 C25 1.368(3) . ?
C24 H24 0.9300 . ?
C25 C26 1.377(3) . ?
C25 H25 0.9300 . ?
C26 C27 1.376(3) . ?
C26 H26 0.9300 . ?
C27 H27 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
O3 S1 O2 119.86(9) . . ?
O3 S1 N1 107.28(8) . . ?
O2 S1 N1 105.88(8) . . ?
O3 S1 C15 109.51(9) . . ?
O2 S1 C15 107.70(8) . . ?
N1 S1 C15 105.72(7) . . ?
C2 O1 C4 112.08(12) . . ?
C7 N1 C6 105.98(13) . . ?
C7 N1 S1 126.33(11) . . ?
C6 N1 S1 119.40(11) . . ?
C7 N2 C5 109.38(14) . . ?
C5 C1 C2 110.59(13) . . ?
C5 C1 H1A 109.5 . . ?
C2 C1 H1A 109.5 . . ?
C5 C1 H1B 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 108.1 . . ?
O1 C2 C22 108.62(13) . . ?
O1 C2 C1 110.27(13) . . ?
C22 C2 C1 112.20(13) . . ?
O1 C2 H2 108.6 . . ?
C22 C2 H2 108.6 . . ?
C1 C2 H2 108.6 . . ?
C4 C3 C5 113.87(13) . . ?
C4 C3 H3A 108.8 . . ?
C5 C3 H3A 108.8 . . ?
C4 C3 H3B 108.8 . . ?
C5 C3 H3B 108.8 . . ?
H3A C3 H3B 107.7 . . ?
O1 C4 C9 107.49(13) . . ?
O1 C4 C3 110.62(12) . . ?
C9 C4 C3 111.67(13) . . ?
O1 C4 H4 109.0 . . ?
C9 C4 H4 109.0 . . ?
C3 C4 H4 109.0 . . ?
N2 C5 C1 111.10(13) . . ?
N2 C5 C3 107.09(13) . . ?
C1 C5 C3 108.47(13) . . ?
N2 C5 C6 104.22(13) . . ?
C1 C5 C6 112.31(13) . . ?
C3 C5 C6 113.50(13) . . ?
N1 C6 C5 102.71(13) . . ?
N1 C6 H6A 111.2 . . ?
C5 C6 H6A 111.2 . . ?
N1 C6 H6B 111.2 . . ?
C5 C6 H6B 111.2 . . ?
H6A C6 H6B 109.1 . . ?
N2 C7 N1 114.46(14) . . ?
N2 C7 C8 123.60(17) . . ?
N1 C7 C8 121.73(16) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C10 C9 C14 118.94(17) . . ?
C10 C9 C4 120.79(16) . . ?
C14 C9 C4 120.27(16) . . ?
C9 C10 C11 120.3(2) . . ?
C9 C10 H10 119.9 . . ?
C11 C10 H10 119.9 . . ?
C12 C11 C10 120.3(2) . . ?
C12 C11 H11 119.9 . . ?
C10 C11 H11 119.9 . . ?
C11 C12 C13 120.0(2) . . ?
C11 C12 H12 120.0 . . ?
C13 C12 H12 120.0 . . ?
C14 C13 C12 119.8(2) . . ?
C14 C13 H13 120.1 . . ?
C12 C13 H13 120.1 . . ?
C13 C14 C9 120.6(2) . . ?
C13 C14 H14 119.7 . . ?
C9 C14 H14 119.7 . . ?
C20 C15 C16 120.11(18) . . ?
C20 C15 S1 120.41(15) . . ?
C16 C15 S1 119.38(14) . . ?
C17 C16 C15 119.59(19) . . ?
C17 C16 H16 120.2 . . ?
C15 C16 H16 120.2 . . ?
C16 C17 C18 121.7(2) . . ?
C16 C17 H17 119.2 . . ?
C18 C17 H17 119.2 . . ?
C17 C18 C19 118.0(2) . . ?
C17 C18 C21 121.3(3) . . ?
C19 C18 C21 120.6(2) . . ?
C18 C19 C20 121.8(2) . . ?
C18 C19 H19 119.1 . . ?
C20 C19 H19 119.1 . . ?
C15 C20 C19 118.7(2) . . ?
C15 C20 H20 120.6 . . ?
C19 C20 H20 120.6 . . ?
C18 C21 H21A 109.5 . . ?
C18 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C18 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C23 C22 C27 118.58(16) . . ?
C23 C22 C2 122.58(16) . . ?
C27 C22 C2 118.83(15) . . ?
C22 C23 C24 120.25(18) . . ?
C22 C23 H23 119.9 . . ?
C24 C23 H23 119.9 . . ?
C25 C24 C23 120.07(19) . . ?
C25 C24 H24 120.0 . . ?
C23 C24 H24 120.0 . . ?
C24 C25 C26 120.22(18) . . ?
C24 C25 H25 119.9 . . ?
C26 C25 H25 119.9 . . ?
C27 C26 C25 119.8(2) . . ?
C27 C26 H26 120.1 . . ?
C25 C26 H26 120.1 . . ?
C26 C27 C22 121.08(19) . . ?
C26 C27 H27 119.5 . . ?
C22 C27 H27 119.5 . . ?

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
O3 S1 N1 C7 -38.21(16) . . . . ?
O2 S1 N1 C7 -167.30(14) . . . . ?
C15 S1 N1 C7 78.59(15) . . . . ?
O3 S1 N1 C6 178.02(13) . . . . ?
O2 S1 N1 C6 48.93(14) . . . . ?
C15 S1 N1 C6 -65.18(14) . . . . ?
C4 O1 C2 C22 173.71(13) . . . . ?
C4 O1 C2 C1 -62.96(16) . . . . ?
C5 C1 C2 O1 60.28(17) . . . . ?
C5 C1 C2 C22 -178.49(14) . . . . ?
C2 O1 C4 C9 -179.91(13) . . . . ?
C2 O1 C4 C3 57.92(17) . . . . ?
C5 C3 C4 O1 -51.87(18) . . . . ?
C5 C3 C4 C9 -171.55(14) . . . . ?
C7 N2 C5 C1 -136.89(16) . . . . ?
C7 N2 C5 C3 104.82(16) . . . . ?
C7 N2 C5 C6 -15.73(18) . . . . ?
C2 C1 C5 N2 -170.00(13) . . . . ?
C2 C1 C5 C3 -52.54(18) . . . . ?
C2 C1 C5 C6 73.72(17) . . . . ?
C4 C3 C5 N2 169.34(13) . . . . ?
C4 C3 C5 C1 49.36(18) . . . . ?
C4 C3 C5 C6 -76.21(17) . . . . ?
C7 N1 C6 C5 -14.01(16) . . . . ?
S1 N1 C6 C5 136.30(12) . . . . ?
N2 C5 C6 N1 17.60(16) . . . . ?
C1 C5 C6 N1 137.95(13) . . . . ?
C3 C5 C6 N1 -98.55(15) . . . . ?
C5 N2 C7 N1 7.1(2) . . . . ?
C5 N2 C7 C8 -178.13(17) . . . . ?
C6 N1 C7 N2 5.1(2) . . . . ?
S1 N1 C7 N2 -142.57(14) . . . . ?
C6 N1 C7 C8 -169.81(17) . . . . ?
S1 N1 C7 C8 42.6(2) . . . . ?
O1 C4 C9 C10 122.03(17) . . . . ?
C3 C4 C9 C10 -116.46(18) . . . . ?
O1 C4 C9 C14 -58.6(2) . . . . ?
C3 C4 C9 C14 63.0(2) . . . . ?
C14 C9 C10 C11 -0.1(3) . . . . ?
C4 C9 C10 C11 179.34(17) . . . . ?
C9 C10 C11 C12 0.3(3) . . . . ?
C10 C11 C12 C13 -0.7(4) . . . . ?
C11 C12 C13 C14 0.8(4) . . . . ?
C12 C13 C14 C9 -0.5(4) . . . . ?
C10 C9 C14 C13 0.2(3) . . . . ?
C4 C9 C14 C13 -179.26(18) . . . . ?
O3 S1 C15 C20 24.91(17) . . . . ?
O2 S1 C15 C20 156.79(14) . . . . ?
N1 S1 C15 C20 -90.37(15) . . . . ?
O3 S1 C15 C16 -158.74(14) . . . . ?
O2 S1 C15 C16 -26.87(16) . . . . ?
N1 S1 C15 C16 85.98(15) . . . . ?
C20 C15 C16 C17 1.5(3) . . . . ?
S1 C15 C16 C17 -174.82(14) . . . . ?
C15 C16 C17 C18 -0.4(3) . . . . ?
C16 C17 C18 C19 -1.8(3) . . . . ?
C16 C17 C18 C21 177.9(2) . . . . ?
C17 C18 C19 C20 2.9(3) . . . . ?
C21 C18 C19 C20 -176.8(2) . . . . ?
C16 C15 C20 C19 -0.4(3) . . . . ?
S1 C15 C20 C19 175.88(14) . . . . ?
C18 C19 C20 C15 -1.8(3) . . . . ?
O1 C2 C22 C23 19.5(2) . . . . ?
C1 C2 C22 C23 -102.70(18) . . . . ?
O1 C2 C22 C27 -161.74(14) . . . . ?
C1 C2 C22 C27 76.09(19) . . . . ?
C27 C22 C23 C24 0.6(3) . . . . ?
C2 C22 C23 C24 179.41(16) . . . . ?
C22 C23 C24 C25 -0.9(3) . . . . ?
C23 C24 C25 C26 0.4(3) . . . . ?
C24 C25 C26 C27 0.3(3) . . . . ?
C25 C26 C27 C22 -0.5(3) . . . . ?
C23 C22 C27 C26 0.1(3) . . . . ?
C2 C22 C27 C26 -178.77(17) . . . . ?

#==============================================================================

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.

#==============================================================================
#     End of CIF
#==============================================================================
####################################################################### 
# 
# 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_kt3_a
_database_code_depnum_ccdc_archive 'CCDC 2168732'
loop_
_audit_author_name
_audit_author_address
'Jaekyun Lee'
;Korea Institute of Science and Technology
South Korea
;
_audit_update_record             
;
2022-04-26 deposited with the CCDC.	2022-11-30 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         ?
_chemical_formula_sum            'C24 H22 N2 O2'
_chemical_formula_weight         370.43

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'

_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                   7.1626(14)
_cell_length_b                   17.647(4)
_cell_length_c                   7.7716(16)
_cell_angle_alpha                90
_cell_angle_beta                 102.13(3)
_cell_angle_gamma                90
_cell_volume                     960.4(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    5766
_cell_measurement_theta_min      3.13
_cell_measurement_theta_max      27.545

_exptl_crystal_description       ~8,15
_exptl_crystal_colour            ~8,15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.281
_exptl_crystal_F_000             392
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.082
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.5783
_exptl_absorpt_correction_T_max  1.0000
_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                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'CCD detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8181
_diffrn_reflns_av_unetI/netI     0.0408
_diffrn_reflns_av_R_equivalents  0.0513
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         3.130
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             1885
_reflns_number_gt                1172
_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 APEX software'
_computing_cell_refinement       'Bruker APEX software'
_computing_data_reduction        'Bruker APEX software'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  SHELXL
_computing_molecular_graphics    ORTEP
_computing_publication_material  CIFTAB
_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)+(0.0724P)²+0.0277P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_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         1885
_refine_ls_number_parameters     127
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0819
_refine_ls_R_factor_gt           0.0474
_refine_ls_wR_factor_ref         0.1448
_refine_ls_wR_factor_gt          0.1227
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_restrained_S_all      1.076
_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
O1 O 0.8320(2) 0.58261(9) 0.62474(19) 0.0630(5) Uani 1 1 d . . . . .
N1 N 0.5681(2) 0.54241(9) 0.7243(2) 0.0480(4) Uani 1 1 d . . . . .
C1 C 0.6619(3) 0.58724(11) 0.6290(2) 0.0473(5) Uani 1 1 d . . . . .
C2 C 0.5195(3) 0.64001(11) 0.5314(2) 0.0466(5) Uani 1 1 d . . . . .
C3 C 0.5415(3) 0.69697(12) 0.4144(3) 0.0577(6) Uani 1 1 d . . . . .
H3 H 0.660177 0.707438 0.389220 0.069 Uiso 1 1 calc R U . . .
C4 C 0.3812(4) 0.73764(14) 0.3367(3) 0.0688(7) Uani 1 1 d . . . . .
H4 H 0.391813 0.776723 0.259027 0.083 Uiso 1 1 calc R U . . .
C5 C 0.2057(4) 0.72086(14) 0.3730(3) 0.0733(7) Uani 1 1 d . . . . .
H5 H 0.099463 0.748673 0.318228 0.088 Uiso 1 1 calc R U . . .
C6 C 0.1832(3) 0.66389(13) 0.4886(3) 0.0628(6) Uani 1 1 d . . . . .
H6 H 0.064077 0.653042 0.512302 0.075 Uiso 1 1 calc R U . . .
C7 C 0.3432(3) 0.62352(11) 0.5680(3) 0.0484(5) Uani 1 1 d . . . . .
C8 C 0.3606(3) 0.55741(11) 0.6930(3) 0.0484(5) Uani 1 1 d . . . . .
H8 H 0.291806 0.513994 0.631273 0.058 Uiso 1 1 calc R U . . .
C9 C 0.6601(3) 0.47917(12) 0.8290(3) 0.0517(5) Uani 1 1 d . . . . .
H9A H 0.772198 0.464630 0.785210 0.062 Uiso 1 1 calc R U . . .
H9B H 0.573113 0.436389 0.811813 0.062 Uiso 1 1 calc R U . . .
C10 C 0.7198(3) 0.49456(12) 1.0231(3) 0.0477(5) Uani 1 1 d . . . . .
C11 C 0.7829(3) 0.56149(14) 1.0835(3) 0.0626(6) Uani 1 1 d . . . . .
H11A H 0.791434 0.600704 1.005604 0.075 Uiso 1 1 calc R U . . .
H11B H 0.818974 0.569594 1.204211 0.075 Uiso 1 1 calc R U . . .
C12 C 0.7151(3) 0.42682(11) 1.1418(2) 0.0518(5) Uani 1 1 d . . . . .
H12A H 0.843622 0.406790 1.176643 0.062 Uiso 1 1 calc R U . . .
H12B H 0.636602 0.387783 1.074442 0.062 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
O1 C1 1.228(2) . ?
N1 C1 1.354(2) . ?
N1 C9 1.455(2) . ?
N1 C8 1.479(2) . ?
C1 C2 1.469(3) . ?
C2 C7 1.382(3) . ?
C2 C3 1.386(3) . ?
C3 C4 1.381(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.377(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.380(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.380(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.506(3) . ?
C8 C12 1.521(3) 3_667 ?
C8 H8 0.9800 . ?
C9 C10 1.504(3) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.316(3) . ?
C10 C12 1.515(3) . ?
C11 H11A 0.9300 . ?
C11 H11B 0.9300 . ?
C12 H12A 0.9700 . ?
C12 H12B 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 N1 C9 122.37(17) . . ?
C1 N1 C8 113.74(16) . . ?
C9 N1 C8 123.41(16) . . ?
O1 C1 N1 125.78(19) . . ?
O1 C1 C2 127.81(18) . . ?
N1 C1 C2 106.39(16) . . ?
C7 C2 C3 121.49(19) . . ?
C7 C2 C1 108.99(17) . . ?
C3 C2 C1 129.49(19) . . ?
C4 C3 C2 117.7(2) . . ?
C4 C3 H3 121.1 . . ?
C2 C3 H3 121.1 . . ?
C5 C4 C3 120.6(2) . . ?
C5 C4 H4 119.7 . . ?
C3 C4 H4 119.7 . . ?
C4 C5 C6 121.8(2) . . ?
C4 C5 H5 119.1 . . ?
C6 C5 H5 119.1 . . ?
C7 C6 C5 117.9(2) . . ?
C7 C6 H6 121.1 . . ?
C5 C6 H6 121.1 . . ?
C6 C7 C2 120.53(19) . . ?
C6 C7 C8 129.52(19) . . ?
C2 C7 C8 109.91(16) . . ?
N1 C8 C7 100.86(15) . . ?
N1 C8 C12 114.73(16) . 3_667 ?
C7 C8 C12 114.02(17) . 3_667 ?
N1 C8 H8 109.0 . . ?
C7 C8 H8 109.0 . . ?
C12 C8 H8 109.0 3_667 . ?
N1 C9 C10 114.99(17) . . ?
N1 C9 H9A 108.5 . . ?
C10 C9 H9A 108.5 . . ?
N1 C9 H9B 108.5 . . ?
C10 C9 H9B 108.5 . . ?
H9A C9 H9B 107.5 . . ?
C11 C10 C9 121.63(19) . . ?
C11 C10 C12 122.75(18) . . ?
C9 C10 C12 115.49(17) . . ?
C10 C11 H11A 120.0 . . ?
C10 C11 H11B 120.0 . . ?
H11A C11 H11B 120.0 . . ?
C10 C12 C8 115.30(17) . 3_667 ?
C10 C12 H12A 108.4 . . ?
C8 C12 H12A 108.4 3_667 . ?
C10 C12 H12B 108.4 . . ?
C8 C12 H12B 108.4 3_667 . ?
H12A C12 H12B 107.5 . . ?

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
C9 N1 C1 O1 -3.2(3) . . . . ?
C8 N1 C1 O1 -175.60(19) . . . . ?
C9 N1 C1 C2 175.53(16) . . . . ?
C8 N1 C1 C2 3.2(2) . . . . ?
O1 C1 C2 C7 177.1(2) . . . . ?
N1 C1 C2 C7 -1.6(2) . . . . ?
O1 C1 C2 C3 -0.8(4) . . . . ?
N1 C1 C2 C3 -179.5(2) . . . . ?
C7 C2 C3 C4 0.8(3) . . . . ?
C1 C2 C3 C4 178.44(19) . . . . ?
C2 C3 C4 C5 -1.0(3) . . . . ?
C3 C4 C5 C6 0.6(4) . . . . ?
C4 C5 C6 C7 0.0(4) . . . . ?
C5 C6 C7 C2 -0.2(3) . . . . ?
C5 C6 C7 C8 -177.6(2) . . . . ?
C3 C2 C7 C6 -0.2(3) . . . . ?
C1 C2 C7 C6 -178.29(18) . . . . ?
C3 C2 C7 C8 177.69(18) . . . . ?
C1 C2 C7 C8 -0.4(2) . . . . ?
C1 N1 C8 C7 -3.3(2) . . . . ?
C9 N1 C8 C7 -175.55(17) . . . . ?
C1 N1 C8 C12 -126.28(19) . . . 3_667 ?
C9 N1 C8 C12 61.4(2) . . . 3_667 ?
C6 C7 C8 N1 179.7(2) . . . . ?
C2 C7 C8 N1 2.1(2) . . . . ?
C6 C7 C8 C12 -56.8(3) . . . 3_667 ?
C2 C7 C8 C12 125.57(18) . . . 3_667 ?
C1 N1 C9 C10 101.1(2) . . . . ?
C8 N1 C9 C10 -87.3(2) . . . . ?
N1 C9 C10 C11 -35.4(3) . . . . ?
N1 C9 C10 C12 148.67(17) . . . . ?
C11 C10 C12 C8 44.7(3) . . . 3_667 ?
C9 C10 C12 C8 -139.39(18) . . . 3_667 ?

_refine_diff_density_max         0.242
_refine_diff_density_min         -0.174
_refine_diff_density_rms         0.039






















