# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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_20210827a
_database_code_depnum_ccdc_archive 'CCDC 2170479'
loop_
_audit_author_name
_audit_author_address
'Guofu Zi'
;Beijing Normal University
China
;
_audit_update_record             
;
2022-05-04 deposited with the CCDC.	2022-10-03 downloaded from the CCDC.
;
_audit_creation_date             2021-08-27
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        
'ethyl 2-(5-phenyl-1,3,4-oxadiazol-2-yl)acetate'
_chemical_formula_moiety         'C12 H12 N2 O3'
_chemical_formula_sum            'C12 H12 N2 O3'
_chemical_formula_weight         232.24
_chemical_melting_point          ?
_chemical_oxdiff_formula         C1H1N1O1
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'

_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.6320(5)
_cell_length_b                   8.3085(7)
_cell_length_c                   12.2276(16)
_cell_angle_alpha                85.953(9)
_cell_angle_beta                 80.093(9)
_cell_angle_gamma                75.863(7)
_cell_volume                     546.33(10)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1501
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.2550
_cell_measurement_theta_min      4.2980
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89951
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.412
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             244
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0441
_diffrn_reflns_av_unetI/netI     0.0812
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.819
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            4184
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.819
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.659
_diffrn_reflns_theta_min         3.384
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3127
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.819
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω      1.00  53.00   1.00    1.00    --   12.53 -99.00 120.00   52
  2  ω    -54.00 -21.00   1.00    1.00    --   12.53 -57.00 120.00   33
  3  ω     12.00  37.00   1.00    1.00    --   12.53 -57.00 120.00   25
  4  ω      2.00  85.00   1.00    1.00    --   12.53  57.00  30.00   83
  5  ω    -11.00  84.00   1.00    1.00    --   12.53  57.00 -90.00   95
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1204015000
_diffrn_orient_matrix_UB_12      -0.0102377000
_diffrn_orient_matrix_UB_13      0.0224056000
_diffrn_orient_matrix_UB_21      0.0337941000
_diffrn_orient_matrix_UB_22      -0.0128182000
_diffrn_orient_matrix_UB_23      0.0537671000
_diffrn_orient_matrix_UB_31      -0.0408672000
_diffrn_orient_matrix_UB_32      0.0865341000
_diffrn_orient_matrix_UB_33      0.0088236000
_diffrn_oxdiff_digest_frames     
;
01944a6fcc01521f6fca6c0adef704e365000329153
;
_diffrn_oxdiff_digest_hkl        
;
012dd4278ab5d36066476650dc1b45d67578fb
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1911
_reflns_number_total             2534
_reflns_odcompleteness_completeness 99.73
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.257
_refine_diff_density_min         -0.275
_refine_diff_density_rms         0.062
_refine_ls_extinction_coef       0.026(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     156
_refine_ls_number_reflns         2534
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0735
_refine_ls_R_factor_gt           0.0544
_refine_ls_restrained_S_all      1.047
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0430P)²+0.0408P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1159
_refine_ls_wR_factor_ref         0.1323
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C11(H11A,H11B)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C7(H7), C8(H8)
2.c Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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
O1 O 0.3729(2) 0.67067(14) 0.36114(10) 0.0156(3) Uani 1 1 d . . . . .
O2 O 0.1815(2) 0.83940(15) 0.14661(10) 0.0221(3) Uani 1 1 d . . . . .
O3 O 0.1918(2) 0.64512(14) 0.02435(10) 0.0178(3) Uani 1 1 d . . . . .
N1 N 0.7761(3) 0.58237(18) 0.36382(12) 0.0196(4) Uani 1 1 d . . . . .
N2 N 0.7213(3) 0.52590(19) 0.26742(12) 0.0196(4) Uani 1 1 d . . . . .
C1 C 0.5676(3) 0.6663(2) 0.41535(14) 0.0148(4) Uani 1 1 d . . . . .
C2 C 0.4856(3) 0.5798(2) 0.26988(14) 0.0149(4) Uani 1 1 d . . . . .
C3 C 0.5222(3) 0.7547(2) 0.51908(14) 0.0153(4) Uani 1 1 d . . . . .
C4 C 0.2940(3) 0.8621(2) 0.55427(15) 0.0176(4) Uani 1 1 d . . . . .
H4 H 0.1649 0.8738 0.5138 0.021 Uiso 1 1 calc R . . . .
C5 C 0.2589(3) 0.9518(2) 0.64967(16) 0.0210(4) Uani 1 1 d . . . . .
H5 H 0.1064 1.0234 0.6735 0.025 Uiso 1 1 calc R . . . .
C6 C 0.4523(4) 0.9339(2) 0.70917(15) 0.0217(4) Uani 1 1 d . . . . .
H6 H 0.4301 0.9951 0.7725 0.026 Uiso 1 1 calc R . . . .
C7 C 0.6786(4) 0.8255(2) 0.67512(15) 0.0213(4) Uani 1 1 d . . . . .
H7 H 0.8067 0.8131 0.7162 0.026 Uiso 1 1 calc R . . . .
C8 C 0.7148(3) 0.7356(2) 0.58016(15) 0.0175(4) Uani 1 1 d . . . . .
H8 H 0.8668 0.6629 0.5573 0.021 Uiso 1 1 calc R . . . .
C9 C 0.3368(3) 0.5475(2) 0.18929(15) 0.0177(4) Uani 1 1 d . . . . .
H9A H 0.2012 0.5034 0.2295 0.021 Uiso 1 1 calc R . . . .
H9B H 0.4400 0.4625 0.1398 0.021 Uiso 1 1 calc R . . . .
C10 C 0.2302(3) 0.6968(2) 0.11992(14) 0.0159(4) Uani 1 1 d . . . . .
C11 C 0.0560(3) 0.7698(2) -0.04708(15) 0.0192(4) Uani 1 1 d . . . . .
H11A H 0.0982 0.7341 -0.1233 0.023 Uiso 1 1 calc R . . . .
H11B H 0.1027 0.8742 -0.0443 0.023 Uiso 1 1 calc R . . . .
C12 C -0.2188(3) 0.7941(2) -0.00924(16) 0.0212(4) Uani 1 1 d . . . . .
H12A H -0.3066 0.8730 -0.0582 0.032 Uiso 1 1 calc GR . . . .
H12B H -0.2612 0.8347 0.0649 0.032 Uiso 1 1 calc GR . . . .
H12C H -0.2638 0.6900 -0.0102 0.032 Uiso 1 1 calc GR . . . .


_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 1.367(2) . ?
O1 C2 1.3634(19) . ?
O2 C10 1.204(2) . ?
O3 C10 1.342(2) . ?
O3 C11 1.462(2) . ?
N1 N2 1.407(2) . ?
N1 C1 1.292(2) . ?
N2 C2 1.289(2) . ?
C1 C3 1.464(2) . ?
C2 C9 1.476(3) . ?
C3 C4 1.392(2) . ?
C3 C8 1.392(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.388(2) . ?
C5 H5 0.9300 . ?
C5 C6 1.384(3) . ?
C6 H6 0.9300 . ?
C6 C7 1.385(3) . ?
C7 H7 0.9300 . ?
C7 C8 1.383(2) . ?
C8 H8 0.9300 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C10 1.511(3) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C12 1.505(2) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?

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 O1 C1 102.21(12) . . ?
C10 O3 C11 117.11(13) . . ?
C1 N1 N2 105.96(15) . . ?
C2 N2 N1 106.38(13) . . ?
O1 C1 C3 119.12(14) . . ?
N1 C1 O1 112.71(15) . . ?
N1 C1 C3 128.15(17) . . ?
O1 C2 C9 120.13(14) . . ?
N2 C2 O1 112.74(16) . . ?
N2 C2 C9 127.08(15) . . ?
C4 C3 C1 120.91(17) . . ?
C4 C3 C8 120.07(16) . . ?
C8 C3 C1 118.96(15) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 C3 120.06(18) . . ?
C5 C4 H4 120.0 . . ?
C4 C5 H5 120.2 . . ?
C6 C5 C4 119.55(17) . . ?
C6 C5 H5 120.2 . . ?
C5 C6 H6 119.8 . . ?
C5 C6 C7 120.49(17) . . ?
C7 C6 H6 119.8 . . ?
C6 C7 H7 119.9 . . ?
C8 C7 C6 120.24(19) . . ?
C8 C7 H7 119.9 . . ?
C3 C8 H8 120.2 . . ?
C7 C8 C3 119.57(17) . . ?
C7 C8 H8 120.2 . . ?
C2 C9 H9A 108.5 . . ?
C2 C9 H9B 108.5 . . ?
C2 C9 C10 115.07(14) . . ?
H9A C9 H9B 107.5 . . ?
C10 C9 H9A 108.5 . . ?
C10 C9 H9B 108.5 . . ?
O2 C10 O3 125.11(18) . . ?
O2 C10 C9 125.84(17) . . ?
O3 C10 C9 109.03(14) . . ?
O3 C11 H11A 109.7 . . ?
O3 C11 H11B 109.7 . . ?
O3 C11 C12 109.99(15) . . ?
H11A C11 H11B 108.2 . . ?
C12 C11 H11A 109.7 . . ?
C12 C11 H11B 109.7 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?

_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 1.331
_oxdiff_exptl_absorpt_empirical_full_min 0.707
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
####################################################################### 
# 
# 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_lfy_zl_1303_02_s_auto
_database_code_depnum_ccdc_archive 'CCDC 2178538'
loop_
_audit_author_name
_audit_author_address
'Jun Xu'
;School of Pharmaceutical Science and Technology, Tianjin University
China
;
_audit_update_record             
;
2022-06-12 deposited with the CCDC.	2022-10-03 downloaded from the CCDC.
;
_audit_creation_date             2022-06-11
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H14 N2 O2 S'
_chemical_formula_sum            'C16 H14 N2 O2 S'
_chemical_formula_weight         298.35
_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 0.0033 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'

_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.7462(4)
_cell_length_b                   9.2543(4)
_cell_length_c                   10.7494(5)
_cell_angle_alpha                106.819(4)
_cell_angle_beta                 100.376(4)
_cell_angle_gamma                93.807(4)
_cell_volume                     719.78(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4653
_cell_measurement_temperature    300.14(10)
_cell_measurement_theta_max      30.3390
_cell_measurement_theta_min      3.6170
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.230
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.65079
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.123a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.377
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       ?
_exptl_crystal_F_000             312
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0221
_diffrn_reflns_av_unetI/netI     0.0343
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.783
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            9033
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.783
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.912
_diffrn_reflns_theta_min         3.515
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      300.14(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.783
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -7.00  20.00   0.50    5.00    --    4.99  57.00  30.00   54
  2  ω     52.00  78.00   0.50    5.00    --    4.99  57.00  30.00   52
  3  ω    -22.00  66.00   0.50    5.00    --   -6.71  57.00 150.00  176
  4  ω    -72.00 -26.00   0.50    5.00    --   -6.71 -57.00 150.00   92
  5  ω    -24.00   6.00   0.50    5.00    --   -6.71 -57.00 150.00   60
  6  ω    -23.00  28.00   0.50    5.00    --   -6.71 -99.00 -30.00  102
  7  ω    -23.00   3.00   0.50    5.00    --   -6.71 -99.00  90.00   52
  8  ω     -9.00  69.00   0.50    5.00    --   -6.71  19.00 -90.00  156
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at offset/far, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0501599000
_diffrn_orient_matrix_UB_12      -0.0572915000
_diffrn_orient_matrix_UB_13      -0.0286953000
_diffrn_orient_matrix_UB_21      -0.0568320000
_diffrn_orient_matrix_UB_22      -0.0136194000
_diffrn_orient_matrix_UB_23      -0.0629130000
_diffrn_orient_matrix_UB_31      0.0553099000
_diffrn_orient_matrix_UB_32      0.0551972000
_diffrn_orient_matrix_UB_33      -0.0136662000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2468
_reflns_number_total             3569
_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 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.175
_refine_diff_density_min         -0.167
_refine_diff_density_rms         0.032
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         3569
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0642
_refine_ls_R_factor_gt           0.0392
_refine_ls_restrained_S_all      1.039
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0530P)²+0.0335P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0990
_refine_ls_wR_factor_ref         0.1088
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C11(H11A,H11B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C27(H27), C28(H28), C34(H34), C20(H20), C10(H10), C16(H16)
2.c Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C)
;
_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
S35 S 0.67397(5) 0.33823(5) 0.45716(4) 0.05424(15) Uani 1 1 d . . . . .
O29 O 0.41589(15) -0.11692(12) 0.16440(11) 0.0623(3) Uani 1 1 d . . . . .
O2 O 0.58786(18) 0.01358(14) 0.36179(12) 0.0747(4) Uani 1 1 d . . . . .
N31 N 0.5853(2) 0.40433(15) 0.24362(13) 0.0621(4) Uani 1 1 d . . . . .
N7 N 0.6763(2) 0.53612(15) 0.33552(13) 0.0632(4) Uani 1 1 d . . . . .
C15 C 0.57317(19) 0.29242(17) 0.29225(14) 0.0478(3) Uani 1 1 d . . . . .
C33 C 0.72816(19) 0.51942(17) 0.45188(15) 0.0473(3) Uani 1 1 d . . . . .
C22 C 0.82644(19) 0.64552(17) 0.56699(14) 0.0477(3) Uani 1 1 d . . . . .
C24 C 0.5016(2) 0.00860(18) 0.25582(16) 0.0541(4) Uani 1 1 d . . . . .
C3 C 0.8353(2) 0.79151(18) 0.56084(15) 0.0503(3) Uani 1 1 d . . . . .
H3 H 0.775255 0.810491 0.485256 0.060 Uiso 1 1 calc R U . . .
C19 C 0.93403(19) 0.91361(18) 0.66713(15) 0.0501(3) Uani 1 1 d . . . . .
C9 C 0.4720(2) 0.14353(17) 0.20710(15) 0.0534(4) Uani 1 1 d . . . . .
H9A H 0.501125 0.121529 0.119979 0.064 Uiso 1 1 calc R U . . .
H9B H 0.346982 0.154357 0.195985 0.064 Uiso 1 1 calc R U . . .
C25 C 1.0247(2) 0.88316(19) 0.78253(15) 0.0533(4) Uani 1 1 d . . . . .
C27 C 0.9142(2) 0.61699(19) 0.68368(16) 0.0562(4) Uani 1 1 d . . . . .
H27 H 0.906681 0.518329 0.689041 0.067 Uiso 1 1 calc R U . . .
C11 C 0.4257(3) -0.2573(2) 0.1998(2) 0.0704(5) Uani 1 1 d . . . . .
H11A H 0.385443 -0.246587 0.281993 0.084 Uiso 1 1 calc R U . . .
H11B H 0.546820 -0.280206 0.212186 0.084 Uiso 1 1 calc R U . . .
C28 C 1.0090(2) 0.7326(2) 0.78739(16) 0.0598(4) Uani 1 1 d . . . . .
H28 H 1.064945 0.712029 0.863383 0.072 Uiso 1 1 calc R U . . .
C34 C 0.9503(2) 1.06438(19) 0.66187(18) 0.0623(4) Uani 1 1 d . . . . .
H34 H 0.890649 1.086241 0.587586 0.075 Uiso 1 1 calc R U . . .
C20 C 1.1269(2) 1.0053(2) 0.88761(17) 0.0650(4) Uani 1 1 d . . . . .
H20 H 1.185188 0.986964 0.964058 0.078 Uiso 1 1 calc R U . . .
C12 C 0.3111(3) -0.3815(2) 0.0900(2) 0.0779(5) Uani 1 1 d . . . . .
H12A H 0.351514 -0.390817 0.009051 0.117 Uiso 1 1 calc R U . . .
H12B H 0.191288 -0.358511 0.079369 0.117 Uiso 1 1 calc R U . . .
H12C H 0.316324 -0.475557 0.110687 0.117 Uiso 1 1 calc R U . . .
C10 C 1.0524(3) 1.1782(2) 0.7645(2) 0.0720(5) Uani 1 1 d . . . . .
H10 H 1.063503 1.276772 0.759039 0.086 Uiso 1 1 calc R U . . .
C16 C 1.1413(3) 1.1479(2) 0.8788(2) 0.0739(5) Uani 1 1 d . . . . .
H16 H 1.210190 1.226482 0.948481 0.089 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
S35 C15 1.7188(15) . ?
S35 C33 1.7209(15) . ?
O29 C24 1.326(2) . ?
O29 C11 1.4584(18) . ?
O2 C24 1.1991(19) . ?
N31 N7 1.3777(19) . ?
N31 C15 1.2934(19) . ?
N7 C33 1.2995(19) . ?
C15 C9 1.489(2) . ?
C33 C22 1.476(2) . ?
C22 C3 1.369(2) . ?
C22 C27 1.419(2) . ?
C24 C9 1.503(2) . ?
C3 H3 0.9300 . ?
C3 C19 1.411(2) . ?
C19 C25 1.423(2) . ?
C19 C34 1.411(2) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C25 C28 1.407(2) . ?
C25 C20 1.414(2) . ?
C27 H27 0.9300 . ?
C27 C28 1.356(2) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C12 1.484(3) . ?
C28 H28 0.9300 . ?
C34 H34 0.9300 . ?
C34 C10 1.362(3) . ?
C20 H20 0.9300 . ?
C20 C16 1.349(3) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C10 H10 0.9300 . ?
C10 C16 1.408(3) . ?
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
C15 S35 C33 87.29(7) . . ?
C24 O29 C11 116.12(13) . . ?
C15 N31 N7 112.96(12) . . ?
C33 N7 N31 112.23(12) . . ?
N31 C15 S35 113.71(12) . . ?
N31 C15 C9 119.62(13) . . ?
C9 C15 S35 126.62(11) . . ?
N7 C33 S35 113.79(12) . . ?
N7 C33 C22 122.18(13) . . ?
C22 C33 S35 124.03(11) . . ?
C3 C22 C33 119.84(13) . . ?
C3 C22 C27 119.45(15) . . ?
C27 C22 C33 120.71(13) . . ?
O29 C24 C9 109.67(13) . . ?
O2 C24 O29 125.03(15) . . ?
O2 C24 C9 125.29(16) . . ?
C22 C3 H3 119.4 . . ?
C22 C3 C19 121.17(14) . . ?
C19 C3 H3 119.4 . . ?
C3 C19 C25 118.87(14) . . ?
C3 C19 C34 122.42(14) . . ?
C34 C19 C25 118.69(15) . . ?
C15 C9 C24 116.75(13) . . ?
C15 C9 H9A 108.1 . . ?
C15 C9 H9B 108.1 . . ?
C24 C9 H9A 108.1 . . ?
C24 C9 H9B 108.1 . . ?
H9A C9 H9B 107.3 . . ?
C28 C25 C19 118.63(15) . . ?
C28 C25 C20 122.64(15) . . ?
C20 C25 C19 118.73(16) . . ?
C22 C27 H27 119.8 . . ?
C28 C27 C22 120.42(15) . . ?
C28 C27 H27 119.8 . . ?
O29 C11 H11A 110.1 . . ?
O29 C11 H11B 110.1 . . ?
O29 C11 C12 107.94(14) . . ?
H11A C11 H11B 108.4 . . ?
C12 C11 H11A 110.1 . . ?
C12 C11 H11B 110.1 . . ?
C25 C28 H28 119.3 . . ?
C27 C28 C25 121.42(14) . . ?
C27 C28 H28 119.3 . . ?
C19 C34 H34 119.7 . . ?
C10 C34 C19 120.66(17) . . ?
C10 C34 H34 119.7 . . ?
C25 C20 H20 119.5 . . ?
C16 C20 C25 121.08(17) . . ?
C16 C20 H20 119.5 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C34 C10 H10 119.7 . . ?
C34 C10 C16 120.51(17) . . ?
C16 C10 H10 119.7 . . ?
C20 C16 C10 120.32(18) . . ?
C20 C16 H16 119.8 . . ?
C10 C16 H16 119.8 . . ?

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
S35 C15 C9 C24 -18.2(2) . . . . ?
S35 C33 C22 C3 -167.92(11) . . . . ?
S35 C33 C22 C27 13.0(2) . . . . ?
O29 C24 C9 C15 -174.27(12) . . . . ?
O2 C24 C9 C15 6.5(2) . . . . ?
N31 N7 C33 S35 1.55(18) . . . . ?
N31 N7 C33 C22 -179.24(12) . . . . ?
N31 C15 C9 C24 164.49(14) . . . . ?
N7 N31 C15 S35 -0.21(18) . . . . ?
N7 N31 C15 C9 177.44(13) . . . . ?
N7 C33 C22 C3 13.0(2) . . . . ?
N7 C33 C22 C27 -166.15(14) . . . . ?
C15 S35 C33 N7 -1.38(12) . . . . ?
C15 S35 C33 C22 179.43(12) . . . . ?
C15 N31 N7 C33 -0.9(2) . . . . ?
C33 S35 C15 N31 0.87(12) . . . . ?
C33 S35 C15 C9 -176.58(13) . . . . ?
C33 C22 C3 C19 -177.46(12) . . . . ?
C33 C22 C27 C28 177.85(13) . . . . ?
C22 C3 C19 C25 -0.3(2) . . . . ?
C22 C3 C19 C34 177.90(13) . . . . ?
C22 C27 C28 C25 -0.5(2) . . . . ?
C24 O29 C11 C12 175.63(14) . . . . ?
C3 C22 C27 C28 -1.3(2) . . . . ?
C3 C19 C25 C28 -1.4(2) . . . . ?
C3 C19 C25 C20 178.51(13) . . . . ?
C3 C19 C34 C10 -177.42(14) . . . . ?
C19 C25 C28 C27 1.8(2) . . . . ?
C19 C25 C20 C16 -1.0(2) . . . . ?
C19 C34 C10 C16 -1.1(3) . . . . ?
C25 C19 C34 C10 0.8(2) . . . . ?
C25 C20 C16 C10 0.7(3) . . . . ?
C27 C22 C3 C19 1.7(2) . . . . ?
C11 O29 C24 O2 1.8(2) . . . . ?
C11 O29 C24 C9 -177.45(13) . . . . ?
C28 C25 C20 C16 178.93(16) . . . . ?
C34 C19 C25 C28 -179.70(14) . . . . ?
C34 C19 C25 C20 0.2(2) . . . . ?
C34 C10 C16 C20 0.3(3) . . . . ?
C20 C25 C28 C27 -178.09(14) . . . . ?

_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 1.646
_oxdiff_exptl_absorpt_empirical_full_min 0.611
####################################################################### 
# 
# 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_lfy_zl_1303_02_n2_auto
_database_code_depnum_ccdc_archive 'CCDC 2178536'
loop_
_audit_author_name
_audit_author_address
'Jun Xu'
;School of Pharmaceutical Science and Technology, Tianjin University
China
;
_audit_update_record             
;
2022-06-12 deposited with the CCDC.	2022-10-03 downloaded from the CCDC.
;
_audit_creation_date             2022-06-11
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H17 N3 O2'
_chemical_formula_sum            'C18 H17 N3 O2'
_chemical_formula_weight         307.34
_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 0.0033 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'

_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/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.4347(6)
_cell_length_b                   5.1670(3)
_cell_length_c                   35.992(2)
_cell_angle_alpha                90
_cell_angle_beta                 92.243(5)
_cell_angle_gamma                90
_cell_volume                     1567.41(17)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4781
_cell_measurement_temperature    300.4(2)
_cell_measurement_theta_max      29.2610
_cell_measurement_theta_min      3.9740
_shelx_estimated_absorpt_T_max   0.996
_shelx_estimated_absorpt_T_min   0.987
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90583
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.123a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_diffrn    1.302
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0356
_diffrn_reflns_av_unetI/netI     0.0383
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.815
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -45
_diffrn_reflns_number            14839
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.815
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.717
_diffrn_reflns_theta_min         3.248
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      300.4(2)
_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 0.815
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -21.00  18.00   0.50  100.00    --   -6.71  58.00 174.00   78
  2  ω    -67.00 -20.00   0.50  100.00    --   -6.71 -58.00  33.00   94
  3  ω    -70.00   0.00   0.50  100.00    --    4.99 -19.00-180.00  140
  4  ω    -22.00  28.00   0.50  100.00    --   -6.71 -99.00  60.00  100
  5  ω    -23.00  26.00   0.50  100.00    --   -6.71 -99.00 -90.00   98
  6  ω     31.00  56.00   0.50  100.00    --   -6.71  58.00 174.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at offset/far, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0204203000
_diffrn_orient_matrix_UB_12      -0.0228822000
_diffrn_orient_matrix_UB_13      0.0190215000
_diffrn_orient_matrix_UB_21      -0.0574363000
_diffrn_orient_matrix_UB_22      0.0920611000
_diffrn_orient_matrix_UB_23      0.0051985000
_diffrn_orient_matrix_UB_31      -0.0580243000
_diffrn_orient_matrix_UB_32      -0.0992261000
_diffrn_orient_matrix_UB_33      0.0004302000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2694
_reflns_number_total             3975
_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 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.167
_refine_diff_density_min         -0.198
_refine_diff_density_rms         0.036
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     250
_refine_ls_number_reflns         3975
_refine_ls_number_restraints     10
_refine_ls_R_factor_all          0.0802
_refine_ls_R_factor_gt           0.0495
_refine_ls_restrained_S_all      1.019
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0623P)²+0.2788P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1210
_refine_ls_wR_factor_ref         0.1339
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C10-C11 \\sim C10-C11A
 with sigma of 0.02
 C25-C35 \\sim C25-C35A
 with sigma of 0.04
 C10-C35 \\sim C10-C35A
 with sigma of 0.02
 C25-C37 \\sim C25-C37A
 with sigma of 0.02
 C25-C31 \\sim C25-C31A
 with sigma of 0.02
 C10-C31 \\sim C10-C31A
 with sigma of 0.04
 C11-C37 \\sim C11A-C37A
 with sigma of 0.02
 C10-C37 \\sim C10-C37A
 with sigma of 0.04
 C35-C31 \\sim C35A-C31A
 with sigma of 0.02
 C25-C11 \\sim C25-C11A
 with sigma of 0.04
3. Others
 Sof(H25A)=Sof(C11A)=Sof(H11A)=Sof(C37A)=Sof(H37A)=Sof(C31A)=Sof(H31A)=
 Sof(C35A)=Sof(H35A)=1-FVAR(1)
 Sof(H25)=Sof(C11)=Sof(H11)=Sof(C35)=Sof(H35)=Sof(C37)=Sof(H37)=Sof(C31)=
 Sof(H31)=FVAR(1)
4.a Secondary CH2 refined with riding coordinates:
 C22(H22A,H22B), C17(H17A,H17B)
4.b Aromatic/amide H refined with riding coordinates:
 C32(H32), C30(H30), C26(H26), C34(H34), C25(H25), C25(H25A), C11(H11),
 C35(H35), C37(H37), C31(H31), C11A(H11A), C37A(H37A), C31A(H31A), C35A(H35A)
4.c Idealised Me refined as rotating group:
 C2(H2A,H2B,H2C)
;
_atom_sites_solution_hydrogens   mixed
_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
O12 O 0.80443(13) 0.6827(2) 0.51155(3) 0.0513(3) Uani 1 1 d . . . . .
N4 N 0.86483(14) 0.3474(2) 0.62534(3) 0.0376(3) Uani 1 1 d . . . . .
O14 O 0.64114(14) 0.5244(3) 0.55349(4) 0.0670(4) Uani 1 1 d . . . . .
N1 N 0.84491(17) -0.0732(2) 0.62347(3) 0.0464(3) Uani 1 1 d . . . . .
N6 N 0.87751(18) -0.0020(2) 0.58815(3) 0.0489(4) Uani 1 1 d . . . . .
C8 C 0.83860(17) 0.1355(2) 0.64533(4) 0.0358(3) Uani 1 1 d . . . . .
C24 C 0.74244(16) 0.1123(3) 0.76149(4) 0.0341(3) Uani 1 1 d . . . . .
C16 C 0.80631(17) 0.1256(2) 0.68506(4) 0.0346(3) Uani 1 1 d . . . . .
C10 C 0.70727(17) 0.1070(3) 0.80175(4) 0.0385(3) Uani 1 1 d D . . . .
C18 C 0.77092(19) 0.5433(3) 0.54151(4) 0.0433(4) Uani 1 1 d . . . . .
C20 C 0.88726(17) 0.2517(3) 0.59063(4) 0.0382(3) Uani 1 1 d . . . . .
C22 C 0.91784(19) 0.4144(3) 0.55750(4) 0.0427(4) Uani 1 1 d . . . . .
H22A H 0.962997 0.306864 0.538521 0.051 Uiso 1 1 calc R U . . .
H22B H 0.995309 0.546248 0.564465 0.051 Uiso 1 1 calc R U . . .
C32 C 0.86984(19) 0.3091(3) 0.70932(4) 0.0441(4) Uani 1 1 d . . . . .
H32 H 0.934300 0.439171 0.700355 0.053 Uiso 1 1 calc R U . . .
C30 C 0.7109(2) -0.0659(3) 0.69935(4) 0.0472(4) Uani 1 1 d . . . . .
H30 H 0.667320 -0.192039 0.683595 0.057 Uiso 1 1 calc R U . . .
C26 C 0.8388(2) 0.3018(3) 0.74669(4) 0.0456(4) Uani 1 1 d . . . . .
H26 H 0.883507 0.427016 0.762415 0.055 Uiso 1 1 calc R U . . .
C34 C 0.6798(2) -0.0713(3) 0.73675(4) 0.0467(4) Uani 1 1 d . . . . .
H34 H 0.615236 -0.201467 0.745636 0.056 Uiso 1 1 calc R U . . .
C25 C 0.6356(3) 0.1030(5) 0.87717(5) 0.0719(6) Uani 1 1 d D . . . .
H25 H 0.607463 0.110203 0.901881 0.086 Uiso 0.52(2) 1 calc R U P A 1
H25A H 0.615995 0.097086 0.902408 0.086 Uiso 0.48(2) 1 calc R U P A 2
C11 C 0.5850(11) -0.0440(19) 0.8153(2) 0.0489(18) Uani 0.52(2) 1 d D . P A 1
H11 H 0.523904 -0.144206 0.798732 0.059 Uiso 0.52(2) 1 calc R U P A 1
C17 C 0.6748(2) 0.8388(4) 0.49635(6) 0.0707(6) Uani 1 1 d . . . . .
H17A H 0.637865 0.955341 0.515294 0.085 Uiso 1 1 calc R U . . .
H17B H 0.587151 0.728054 0.488335 0.085 Uiso 1 1 calc R U . . .
C35 C 0.7950(10) 0.249(2) 0.82817(19) 0.0519(18) Uani 0.52(2) 1 d D . P A 1
H35 H 0.879251 0.348986 0.820501 0.062 Uiso 0.52(2) 1 calc R U P A 1
C37 C 0.5523(13) -0.049(2) 0.8526(2) 0.058(2) Uani 0.52(2) 1 d D . P A 1
H37 H 0.472840 -0.156353 0.860941 0.070 Uiso 0.52(2) 1 calc R U P A 1
C2 C 0.7295(3) 0.9885(5) 0.46466(7) 0.1014(9) Uani 1 1 d . . . . .
H2A H 0.754798 0.872620 0.444889 0.152 Uiso 1 1 calc R U . . .
H2B H 0.822355 1.085560 0.472199 0.152 Uiso 1 1 calc R U . . .
H2C H 0.647294 1.105069 0.456144 0.152 Uiso 1 1 calc R U . . .
C31 C 0.7613(10) 0.246(2) 0.8655(2) 0.063(2) Uani 0.52(2) 1 d D . P A 1
H31 H 0.823533 0.340187 0.882510 0.075 Uiso 0.52(2) 1 calc R U P A 1
C11A C 0.6279(17) -0.098(2) 0.8170(3) 0.063(3) Uani 0.48(2) 1 d D . P A 2
H11A H 0.598123 -0.239018 0.802251 0.075 Uiso 0.48(2) 1 calc R U P A 2
C37A C 0.593(2) -0.095(3) 0.8541(3) 0.083(4) Uani 0.48(2) 1 d D . P A 2
H37A H 0.537415 -0.233858 0.863708 0.100 Uiso 0.48(2) 1 calc R U P A 2
C31A C 0.7099(18) 0.315(2) 0.8616(3) 0.079(3) Uani 0.48(2) 1 d D . P A 2
H31A H 0.734225 0.458782 0.876330 0.095 Uiso 0.48(2) 1 calc R U P A 2
C35A C 0.7482(16) 0.316(2) 0.8245(2) 0.062(2) Uani 0.48(2) 1 d D . P A 2
H35A H 0.801427 0.456739 0.814771 0.074 Uiso 0.48(2) 1 calc R U P A 2
H1 H 0.839(2) -0.244(4) 0.6297(5) 0.068(6) Uiso 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
O12 C18 1.3359(17) . ?
O12 C17 1.449(2) . ?
N4 C8 1.3330(17) . ?
N4 C20 1.3637(18) . ?
O14 C18 1.1962(19) . ?
N1 N6 1.3618(17) . ?
N1 C8 1.3373(18) . ?
N1 H1 0.91(2) . ?
N6 C20 1.3162(19) . ?
C8 C16 1.4671(19) . ?
C24 C10 1.4906(19) . ?
C24 C26 1.391(2) . ?
C24 C34 1.391(2) . ?
C16 C32 1.383(2) . ?
C16 C30 1.387(2) . ?
C10 C11 1.396(8) . ?
C10 C35 1.390(7) . ?
C10 C11A 1.379(10) . ?
C10 C35A 1.390(8) . ?
C18 C22 1.501(2) . ?
C20 C22 1.4900(19) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C32 H32 0.9300 . ?
C32 C26 1.381(2) . ?
C30 H30 0.9300 . ?
C30 C34 1.381(2) . ?
C26 H26 0.9300 . ?
C34 H34 0.9300 . ?
C25 H25 0.9300 . ?
C25 H25A 0.9300 . ?
C25 C37 1.356(8) . ?
C25 C31 1.372(8) . ?
C25 C37A 1.357(11) . ?
C25 C31A 1.391(10) . ?
C11 H11 0.9300 . ?
C11 C37 1.383(9) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C17 C2 1.468(3) . ?
C35 H35 0.9300 . ?
C35 C31 1.383(8) . ?
C37 H37 0.9300 . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C31 H31 0.9300 . ?
C11A H11A 0.9300 . ?
C11A C37A 1.380(10) . ?
C37A H37A 0.9300 . ?
C31A H31A 0.9300 . ?
C31A C35A 1.387(9) . ?
C35A H35A 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
C18 O12 C17 115.12(13) . . ?
C8 N4 C20 103.20(11) . . ?
N6 N1 H1 120.5(12) . . ?
C8 N1 N6 110.19(12) . . ?
C8 N1 H1 129.1(12) . . ?
C20 N6 N1 102.72(12) . . ?
N4 C8 N1 109.50(12) . . ?
N4 C8 C16 126.56(12) . . ?
N1 C8 C16 123.93(12) . . ?
C26 C24 C10 121.77(13) . . ?
C34 C24 C10 121.65(13) . . ?
C34 C24 C26 116.58(13) . . ?
C32 C16 C8 120.62(12) . . ?
C32 C16 C30 118.11(13) . . ?
C30 C16 C8 121.27(13) . . ?
C11 C10 C24 121.8(4) . . ?
C35 C10 C24 122.3(3) . . ?
C35 C10 C11 115.9(5) . . ?
C11A C10 C24 121.3(5) . . ?
C11A C10 C35A 118.4(6) . . ?
C35A C10 C24 120.2(4) . . ?
O12 C18 C22 110.55(13) . . ?
O14 C18 O12 124.10(15) . . ?
O14 C18 C22 125.36(14) . . ?
N4 C20 C22 124.28(13) . . ?
N6 C20 N4 114.37(12) . . ?
N6 C20 C22 121.34(13) . . ?
C18 C22 H22A 109.0 . . ?
C18 C22 H22B 109.0 . . ?
C20 C22 C18 113.02(12) . . ?
C20 C22 H22A 109.0 . . ?
C20 C22 H22B 109.0 . . ?
H22A C22 H22B 107.8 . . ?
C16 C32 H32 119.6 . . ?
C26 C32 C16 120.83(13) . . ?
C26 C32 H32 119.6 . . ?
C16 C30 H30 119.6 . . ?
C34 C30 C16 120.70(14) . . ?
C34 C30 H30 119.6 . . ?
C24 C26 H26 119.1 . . ?
C32 C26 C24 121.89(14) . . ?
C32 C26 H26 119.1 . . ?
C24 C34 H34 119.1 . . ?
C30 C34 C24 121.88(14) . . ?
C30 C34 H34 119.1 . . ?
C37 C25 H25 120.1 . . ?
C37 C25 C31 119.8(5) . . ?
C31 C25 H25 120.1 . . ?
C37A C25 H25A 121.3 . . ?
C37A C25 C31A 117.4(7) . . ?
C31A C25 H25A 121.3 . . ?
C10 C11 H11 119.1 . . ?
C37 C11 C10 121.8(8) . . ?
C37 C11 H11 119.1 . . ?
O12 C17 H17A 109.8 . . ?
O12 C17 H17B 109.8 . . ?
O12 C17 C2 109.34(16) . . ?
H17A C17 H17B 108.3 . . ?
C2 C17 H17A 109.8 . . ?
C2 C17 H17B 109.8 . . ?
C10 C35 H35 118.9 . . ?
C31 C35 C10 122.3(6) . . ?
C31 C35 H35 118.9 . . ?
C25 C37 C11 120.4(8) . . ?
C25 C37 H37 119.8 . . ?
C11 C37 H37 119.8 . . ?
C17 C2 H2A 109.5 . . ?
C17 C2 H2B 109.5 . . ?
C17 C2 H2C 109.5 . . ?
H2A C2 H2B 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C25 C31 C35 119.7(7) . . ?
C25 C31 H31 120.2 . . ?
C35 C31 H31 120.2 . . ?
C10 C11A H11A 119.9 . . ?
C10 C11A C37A 120.2(10) . . ?
C37A C11A H11A 119.9 . . ?
C25 C37A C11A 122.6(11) . . ?
C25 C37A H37A 118.7 . . ?
C11A C37A H37A 118.7 . . ?
C25 C31A H31A 119.5 . . ?
C35A C31A C25 121.1(9) . . ?
C35A C31A H31A 119.5 . . ?
C10 C35A H35A 119.9 . . ?
C31A C35A C10 120.2(8) . . ?
C31A C35A H35A 119.9 . . ?

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
O12 C18 C22 C20 -178.88(13) . . . . ?
N4 C8 C16 C32 -30.7(2) . . . . ?
N4 C8 C16 C30 148.87(16) . . . . ?
N4 C20 C22 C18 -76.94(19) . . . . ?
O14 C18 C22 C20 0.7(2) . . . . ?
N1 N6 C20 N4 0.72(18) . . . . ?
N1 N6 C20 C22 -178.35(13) . . . . ?
N1 C8 C16 C32 149.76(15) . . . . ?
N1 C8 C16 C30 -30.7(2) . . . . ?
N6 N1 C8 N4 0.61(18) . . . . ?
N6 N1 C8 C16 -179.79(14) . . . . ?
N6 C20 C22 C18 102.04(17) . . . . ?
C8 N4 C20 N6 -0.38(18) . . . . ?
C8 N4 C20 C22 178.66(14) . . . . ?
C8 N1 N6 C20 -0.79(18) . . . . ?
C8 C16 C32 C26 179.49(14) . . . . ?
C8 C16 C30 C34 -179.22(14) . . . . ?
C24 C10 C11 C37 -179.9(7) . . . . ?
C24 C10 C35 C31 179.3(5) . . . . ?
C24 C10 C11A C37A -178.1(8) . . . . ?
C24 C10 C35A C31A 177.5(5) . . . . ?
C16 C32 C26 C24 -0.4(3) . . . . ?
C16 C30 C34 C24 -0.2(3) . . . . ?
C10 C24 C26 C32 -179.12(14) . . . . ?
C10 C24 C34 C30 179.39(14) . . . . ?
C10 C11 C37 C25 2.5(15) . . . . ?
C10 C35 C31 C25 -1.3(9) . . . . ?
C10 C11A C37A C25 -1.2(17) . . . . ?
C18 O12 C17 C2 177.81(19) . . . . ?
C20 N4 C8 N1 -0.15(16) . . . . ?
C20 N4 C8 C16 -179.73(14) . . . . ?
C32 C16 C30 C34 0.4(2) . . . . ?
C30 C16 C32 C26 -0.1(2) . . . . ?
C26 C24 C10 C11 165.6(5) . . . . ?
C26 C24 C10 C35 -15.3(6) . . . . ?
C26 C24 C10 C11A -172.0(8) . . . . ?
C26 C24 C10 C35A 10.8(7) . . . . ?
C26 C24 C34 C30 -0.3(2) . . . . ?
C34 C24 C10 C11 -14.1(5) . . . . ?
C34 C24 C10 C35 165.1(6) . . . . ?
C34 C24 C10 C11A 8.3(8) . . . . ?
C34 C24 C10 C35A -168.9(7) . . . . ?
C34 C24 C26 C32 0.5(2) . . . . ?
C25 C31A C35A C10 2.4(11) . . . . ?
C11 C10 C35 C31 -1.5(8) . . . . ?
C17 O12 C18 O14 7.1(3) . . . . ?
C17 O12 C18 C22 -173.33(16) . . . . ?
C35 C10 C11 C37 0.9(10) . . . . ?
C37 C25 C31 C35 4.7(10) . . . . ?
C31 C25 C37 C11 -5.3(14) . . . . ?
C11A C10 C35A C31A 0.2(9) . . . . ?
C37A C25 C31A C35A -4.3(11) . . . . ?
C31A C25 C37A C11A 3.7(15) . . . . ?
C35A C10 C11A C37A -0.9(11) . . . . ?

_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 1.215
_oxdiff_exptl_absorpt_empirical_full_min 0.882
