# Supplementary Information (SI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2026

####################################################################### 
# 
# 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_20250115
_database_code_depnum_ccdc_archive 'CCDC 2417187'
loop_
_audit_author_name
_audit_author_address
'Yuming Li'
;Tianjin University of Science and Technology
China
;
_audit_update_record             
;
2025-01-15 deposited with the CCDC.	2026-04-07 downloaded from the CCDC.
;
_audit_creation_date             2025-01-15
_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        ?
_chemical_formula_moiety         'C18 H17 N O4'
_chemical_formula_sum            'C18 H17 N O4'
_chemical_formula_weight         311.32
_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      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                   8.4269(8)
_cell_length_b                   10.2708(11)
_cell_length_c                   10.7625(12)
_cell_angle_alpha                112.254(4)
_cell_angle_beta                 110.239(4)
_cell_angle_gamma                97.809(4)
_cell_volume                     769.74(14)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3529
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.9350
_cell_measurement_theta_min      3.1630
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.343
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             328
_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  0.0326
_diffrn_reflns_av_unetI/netI     0.0474
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.987
_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       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7305
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.518
_diffrn_reflns_theta_min         2.269
_diffrn_ambient_temperature      293.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2516
_reflns_number_total             3503
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.228
_refine_diff_density_min         -0.160
_refine_diff_density_rms         0.033
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.751
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         3503
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0714
_refine_ls_R_factor_gt           0.0487
_refine_ls_restrained_S_all      0.751
_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)+(0.1090P)²+0.4167P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1353
_refine_ls_wR_factor_ref         0.1604
_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:
 C8(H8A,H8B), C9(H9A,H9B)
2.b Aromatic/amide H refined with riding coordinates:
 C16(H16), C12(H12), C13(H13), C5(H5), C2(H2), C4(H4), C3(H3)
2.c Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C17(H17A,H17B,H17C)
;
_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
O0AA O 0.87981(15) 1.00656(13) 0.64121(13) 0.0442(3) Uani 1 1 d . . . . .
O3 O 0.51135(18) 0.79054(16) 0.07874(14) 0.0582(4) Uani 1 1 d . . . . .
O2 O 0.27515(19) 0.55405(16) -0.00008(15) 0.0646(4) Uani 1 1 d . . . . .
O1 O 0.8997(2) 0.8095(2) 0.91368(17) 0.0813(5) Uani 1 1 d . . . . .
N1 N 0.76877(19) 0.84016(18) 0.70418(16) 0.0468(4) Uani 1 1 d . . . . .
C11 C 0.6651(2) 0.77278(18) 0.43557(17) 0.0363(3) Uani 1 1 d . . . . .
C16 C 0.6604(2) 0.82493(19) 0.33265(18) 0.0396(4) Uani 1 1 d . . . . .
H16 H 0.7464 0.9109 0.3614 0.048 Uiso 1 1 calc R . . . .
C12 C 0.5381(2) 0.6447(2) 0.39184(19) 0.0434(4) Uani 1 1 d . . . . .
H12 H 0.5409 0.6093 0.4601 0.052 Uiso 1 1 calc R . . . .
C15 C 0.5285(2) 0.74961(19) 0.18786(18) 0.0404(4) Uani 1 1 d . . . . .
C6 C 0.9697(2) 0.78499(19) 0.60434(18) 0.0406(4) Uani 1 1 d . . . . .
C7 C 0.8187(2) 0.85084(18) 0.59049(17) 0.0370(4) Uani 1 1 d . . . . .
C14 C 0.3992(2) 0.61946(19) 0.14448(19) 0.0428(4) Uani 1 1 d . . . . .
C18 C 0.6458(3) 0.9134(2) 0.1110(2) 0.0533(5) Uani 1 1 d . . . . .
H18A H 0.6236 0.9245 0.0224 0.080 Uiso 1 1 calc GR . . . .
H18B H 0.7594 0.8977 0.1457 0.080 Uiso 1 1 calc GR . . . .
H18C H 0.6456 1.0012 0.1866 0.080 Uiso 1 1 calc GR . . . .
C13 C 0.4054(2) 0.5677(2) 0.2460(2) 0.0471(4) Uani 1 1 d . . . . .
H13 H 0.3207 0.4809 0.2174 0.057 Uiso 1 1 calc R . . . .
C5 C 1.0609(2) 0.7546(2) 0.5178(2) 0.0535(5) Uani 1 1 d . . . . .
H5 H 1.0343 0.7752 0.4372 0.064 Uiso 1 1 calc R . . . .
C1 C 1.0084(2) 0.7539(2) 0.7237(2) 0.0491(4) Uani 1 1 d . . . . .
C10 C 0.8924(3) 0.8019(2) 0.7964(2) 0.0536(5) Uani 1 1 d . . . . .
C2 C 1.1420(3) 0.6919(2) 0.7624(3) 0.0708(7) Uani 1 1 d . . . . .
H2 H 1.1687 0.6718 0.8434 0.085 Uiso 1 1 calc R . . . .
C17 C 0.1598(3) 0.4120(2) -0.0586(2) 0.0690(6) Uani 1 1 d . . . . .
H17A H 0.0873 0.3762 -0.1630 0.104 Uiso 1 1 calc GR . . . .
H17B H 0.0852 0.4157 -0.0079 0.104 Uiso 1 1 calc GR . . . .
H17C H 0.2279 0.3467 -0.0450 0.104 Uiso 1 1 calc GR . . . .
C8 C 0.7697(3) 1.0682(2) 0.7078(3) 0.0628(6) Uani 1 1 d . . . . .
H8A H 0.6697 1.0765 0.6353 0.075 Uiso 1 1 calc R . . . .
H8B H 0.8371 1.1659 0.7905 0.075 Uiso 1 1 calc R . . . .
C9 C 0.7049(3) 0.9646(3) 0.7618(2) 0.0629(6) Uani 1 1 d . . . . .
H9A H 0.7554 1.0109 0.8697 0.076 Uiso 1 1 calc R . . . .
H9B H 0.5763 0.9337 0.7218 0.076 Uiso 1 1 calc R . . . .
C4 C 1.1945(3) 0.6917(3) 0.5562(3) 0.0772(7) Uani 1 1 d . . . . .
H4 H 1.2589 0.6697 0.5003 0.093 Uiso 1 1 calc R . . . .
C3 C 1.2335(3) 0.6612(3) 0.6766(3) 0.0860(9) Uani 1 1 d . . . . .
H3 H 1.3235 0.6190 0.6996 0.103 Uiso 1 1 calc R . . . .


_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
O0AA C7 1.429(2) . ?
O0AA C8 1.432(2) . ?
O3 C15 1.360(2) . ?
O3 C18 1.416(2) . ?
O2 C14 1.363(2) . ?
O2 C17 1.402(2) . ?
O1 C10 1.214(2) . ?
N1 C7 1.460(2) . ?
N1 C10 1.384(3) . ?
N1 C9 1.458(3) . ?
C11 C16 1.393(2) . ?
C11 C12 1.377(2) . ?
C11 C7 1.520(2) . ?
C16 C15 1.385(2) . ?
C12 C13 1.394(2) . ?
C15 C14 1.404(2) . ?
C6 C7 1.510(2) . ?
C6 C5 1.376(3) . ?
C6 C1 1.381(2) . ?
C14 C13 1.374(2) . ?
C5 C4 1.391(3) . ?
C1 C10 1.475(3) . ?
C1 C2 1.385(3) . ?
C2 C3 1.373(4) . ?
C8 C9 1.516(3) . ?
C4 C3 1.387(4) . ?

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
C7 O0AA C8 106.04(14) . . ?
C15 O3 C18 117.97(14) . . ?
C14 O2 C17 118.42(15) . . ?
C10 N1 C7 111.44(15) . . ?
C10 N1 C9 122.48(16) . . ?
C9 N1 C7 108.12(15) . . ?
C16 C11 C7 119.48(14) . . ?
C12 C11 C16 119.44(15) . . ?
C12 C11 C7 120.89(14) . . ?
C15 C16 C11 120.43(15) . . ?
C11 C12 C13 120.52(15) . . ?
O3 C15 C16 125.31(15) . . ?
O3 C15 C14 114.98(14) . . ?
C16 C15 C14 119.72(15) . . ?
C5 C6 C7 129.60(16) . . ?
C5 C6 C1 121.60(17) . . ?
C1 C6 C7 108.79(15) . . ?
O0AA C7 N1 103.37(13) . . ?
O0AA C7 C11 111.75(12) . . ?
O0AA C7 C6 111.52(13) . . ?
N1 C7 C11 112.97(13) . . ?
N1 C7 C6 103.00(13) . . ?
C6 C7 C11 113.49(13) . . ?
O2 C14 C15 115.12(15) . . ?
O2 C14 C13 125.23(16) . . ?
C13 C14 C15 119.64(15) . . ?
C14 C13 C12 120.25(16) . . ?
C6 C5 C4 117.1(2) . . ?
C6 C1 C10 109.06(16) . . ?
C6 C1 C2 121.3(2) . . ?
C2 C1 C10 129.6(2) . . ?
O1 C10 N1 124.9(2) . . ?
O1 C10 C1 128.8(2) . . ?
N1 C10 C1 106.32(15) . . ?
C3 C2 C1 117.4(2) . . ?
O0AA C8 C9 106.97(16) . . ?
N1 C9 C8 102.92(15) . . ?
C3 C4 C5 121.1(2) . . ?
C2 C3 C4 121.5(2) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_a
_database_code_depnum_ccdc_archive 'CCDC 2540289'
loop_
_audit_author_name
_audit_author_address
'Yuming Li'
;Tianjin University of Science and Technology
China
;
_audit_update_record             
;
2026-03-24 deposited with the CCDC.	2026-04-07 downloaded from the CCDC.
;
_audit_creation_date             2026-03-21
_audit_creation_method           
;
Olex2 1.5
(compiled 2026.03.20 svn.r2bc28608 for OlexSys, GUI svn.r7524)
;
_shelx_SHELXL_version_number     2025/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H17 N O2'
_chemical_formula_sum            'C22 H17 N O2'
_chemical_formula_weight         327.36
_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           12
_space_group_name_H-M_alt        C2/m
_space_group_name_Hall           '-C 2y'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x, -y, z'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z'

_cell_length_a                   18.236(3)
_cell_length_b                   9.0230(19)
_cell_length_c                   13.095(4)
_cell_angle_alpha                90
_cell_angle_beta                 128.825(4)
_cell_angle_gamma                90
_cell_volume                     1678.6(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2055
_cell_measurement_temperature    293.00
_cell_measurement_theta_max      24.47
_cell_measurement_theta_min      2.24
_shelx_estimated_absorpt_T_max   0.993
_shelx_estimated_absorpt_T_min   0.989
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6682
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1136 before and 0.0562 after correction.
The Ratio of minimum to maximum transmission is 0.8964.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.295
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0465
_diffrn_reflns_av_unetI/netI     0.0422
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            7182
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.439
_diffrn_reflns_theta_min         1.996
_diffrn_ambient_temperature      293.00
_diffrn_detector                 CPAD
_diffrn_detector_area_resol_mean 7.41
_diffrn_detector_type            'Bruker PHOTON II'
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE TXS PHOTON II'
_diffrn_measurement_method       'ω and φ shutterless scans'
_diffrn_measurement_specimen_support 'nylon loop'
_diffrn_radiation_monochromator  'Helios Multi-layer Optic'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Turbo X-Ray Source (TXS)'
_diffrn_source_current           40.0
_diffrn_source_power             1.8
_diffrn_source_type              'Rotaing Anode'
_diffrn_source_voltage           45.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1263
_reflns_number_total             1833
_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       'SAINT V8.41 (Bruker, 2024)'
_computing_data_collection       'APEX6 V2024.9-1 (Bruker, 2025)'
_computing_data_reduction        'SAINT V8.41 (Bruker, 2024)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2025/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.117
_refine_diff_density_min         -0.123
_refine_diff_density_rms         0.027
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         1833
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0862
_refine_ls_R_factor_gt           0.0533
_refine_ls_restrained_S_all      1.086
_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)+(0.0416P)²+0.8303P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1169
_refine_ls_wR_factor_ref         0.1344
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Others
 Fixed Sof: O1(0.5) O2(0.5) N1(0.5) C1(0.5) C6(0.5) H6(0.5) C5(0.5) H5(0.5)
 C4(0.5) H4(0.5) C3(0.5) H3(0.5) C2(0.5) C7(0.5) C8(0.5) C11(0.5) H11(0.5)
 C10(0.5) H10(0.5) C9(0.5) C14(0.5) H14(0.5) C13(0.5) H13(0.5) C12(0.5)
 H12(0.5) C15(0.5) H15A(0.5) H15B(0.5) C16(0.5) H16(0.5) C22(0.5) H22(0.5)
 C21(0.5) H21(0.5) C20(0.5) H20(0.5) C19(0.5) H19(0.5) C18(0.5) H18(0.5)
 C17(0.5)
3.a Ternary CH refined with riding coordinates:
 C16(H16)
3.b Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B)
3.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C5(H5), C4(H4), C3(H3), C11(H11), C10(H10), C14(H14), C13(H13),
 C12(H12), C22(H22), C21(H21), C20(H20), C19(H19), C18(H18)
3.d Fitted hexagon refined as free rotating group:
 C6(C5,C4,C3,C2,C7), C11(C10,C9,C14,C13,C12), C22(C21,C20,C19,C18,C17)
;
_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
O1 O 0.10449(16) 0.4445(2) 0.2846(2) 0.0616(7) Uani 0.5 1 d . . P A -1
O2 O 0.37459(13) 0.3199(2) 0.44511(18) 0.0425(5) Uani 0.5 1 d . . P A -1
N1 N 0.22092(16) 0.2761(3) 0.3468(2) 0.0407(6) Uani 0.5 1 d . . P A -1
C1 C 0.1590(2) 0.3891(4) 0.2708(3) 0.0454(8) Uani 0.5 1 d . . P A -1
C6 C 0.28428(13) 0.3769(3) 0.1379(2) 0.0511(8) Uani 0.5 1 d G . P A -1
H6 H 0.337761 0.328476 0.160898 0.061 Uiso 0.5 1 calc R U P A -1
C5 C 0.23466(16) 0.4713(3) 0.03029(19) 0.0633(14) Uani 0.5 1 d G . P A -1
H5 H 0.254948 0.486076 -0.018753 0.076 Uiso 0.5 1 calc R U P A -1
C4 C 0.15472(15) 0.5437(3) -0.00404(18) 0.0613(12) Uani 0.5 1 d G . P A -1
H4 H 0.121526 0.606918 -0.076060 0.074 Uiso 0.5 1 calc R U P A -1
C3 C 0.12440(13) 0.5217(3) 0.0693(2) 0.0583(9) Uani 0.5 1 d G . P A -1
H3 H 0.070916 0.570160 0.046283 0.070 Uiso 0.5 1 calc R U P A -1
C2 C 0.17402(14) 0.4273(3) 0.1769(2) 0.0442(7) Uani 0.5 1 d G . P A -1
C7 C 0.25395(13) 0.3549(2) 0.21123(16) 0.0422(7) Uani 0.5 1 d G . P A -1
C8 C 0.2914(2) 0.2593(4) 0.3277(3) 0.0398(7) Uani 0.5 1 d . . P A -1
C11 C 0.2579(2) -0.1548(3) 0.2576(3) 0.0691(12) Uani 0.5 1 d G . P A -1
H11 H 0.212859 -0.227657 0.230143 0.083 Uiso 0.5 1 calc R U P A -1
C10 C 0.23992(14) -0.0089(4) 0.2698(2) 0.0515(8) Uani 0.5 1 d G . P A -1
H10 H 0.182915 0.015927 0.250505 0.062 Uiso 0.5 1 calc R U P A -1
C9 C 0.30719(18) 0.1000(3) 0.3109(2) 0.0424(8) Uani 0.5 1 d G . P A -1
C14 C 0.39239(15) 0.0630(3) 0.3398(2) 0.0577(14) Uani 0.5 1 d G . P A -1
H14 H 0.437397 0.135868 0.367286 0.069 Uiso 0.5 1 calc R U P A -1
C13 C 0.41033(15) -0.0829(4) 0.3276(2) 0.0692(16) Uani 0.5 1 d G . P A -1
H13 H 0.467342 -0.107714 0.346924 0.083 Uiso 0.5 1 calc R U P A -1
C12 C 0.3431(2) -0.1918(3) 0.2865(3) 0.0753(13) Uani 0.5 1 d G . P A -1
H12 H 0.355075 -0.289478 0.278353 0.090 Uiso 0.5 1 calc R U P A -1
C15 C 0.2682(2) 0.2640(4) 0.4860(3) 0.0486(8) Uani 0.5 1 d . . P A -1
H15A H 0.251478 0.172590 0.505816 0.058 Uiso 0.5 1 calc R U P A -1
H15B H 0.252857 0.347202 0.516471 0.058 Uiso 0.5 1 calc R U P A -1
C16 C 0.3739(2) 0.2654(4) 0.5483(3) 0.0412(7) Uani 0.5 1 d . . P A -1
H16 H 0.398211 0.163743 0.570458 0.049 Uiso 0.5 1 calc R U P A -1
C22 C 0.44191(14) 0.5131(2) 0.65722(15) 0.0479(7) Uani 0.5 1 d G . P A -1
H22 H 0.411892 0.556036 0.575253 0.057 Uiso 0.5 1 calc R U P A -1
C21 C 0.49382(17) 0.60074(18) 0.7693(2) 0.0555(9) Uani 0.5 1 d G . P A -1
H21 H 0.498537 0.702266 0.762256 0.067 Uiso 0.5 1 calc R U P A -1
C20 C 0.53868(14) 0.5366(2) 0.89177(17) 0.0545(18) Uani 0.5 1 d G . P A -1
H20 H 0.573410 0.595228 0.966732 0.065 Uiso 0.5 1 calc R U P A -1
C19 C 0.53162(14) 0.3849(2) 0.90224(14) 0.0587(13) Uani 0.5 1 d G . P A -1
H19 H 0.561638 0.341961 0.984208 0.070 Uiso 0.5 1 calc R U P A -1
C18 C 0.47971(15) 0.29725(18) 0.79020(19) 0.0504(8) Uani 0.5 1 d G . P A -1
H18 H 0.474993 0.195728 0.797207 0.060 Uiso 0.5 1 calc R U P A -1
C17 C 0.43485(12) 0.3614(2) 0.66769(15) 0.0396(7) Uani 0.5 1 d G . P A -1


_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 1.222(4) . ?
O2 C8 1.429(3) . ?
O2 C16 1.444(3) . ?
N1 C1 1.377(4) . ?
N1 C8 1.463(4) . ?
N1 C15 1.451(4) . ?
C1 C2 1.459(4) . ?
C6 H6 0.9300 . ?
C6 C5 1.3900 . ?
C6 C7 1.3900 . ?
C5 H5 0.9300 . ?
C5 C4 1.3900 . ?
C4 H4 0.9300 . ?
C4 C3 1.3900 . ?
C3 H3 0.9300 . ?
C3 C2 1.3900 . ?
C2 C7 1.3900 . ?
C7 C8 1.494(3) . ?
C8 C9 1.508(4) . ?
C11 H11 0.9300 . ?
C11 C10 1.3900 . ?
C11 C12 1.3900 . ?
C10 H10 0.9300 . ?
C10 C9 1.3900 . ?
C9 C14 1.3900 . ?
C14 H14 0.9300 . ?
C14 C13 1.3900 . ?
C13 H13 0.9300 . ?
C13 C12 1.3900 . ?
C12 H12 0.9300 . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 C16 1.553(4) . ?
C16 H16 0.9800 . ?
C16 C17 1.501(3) . ?
C22 H22 0.9300 . ?
C22 C21 1.3900 . ?
C22 C17 1.3900 . ?
C21 H21 0.9300 . ?
C21 C20 1.3900 . ?
C20 H20 0.9300 . ?
C20 C19 1.3900 . ?
C19 H19 0.9300 . ?
C19 C18 1.3900 . ?
C18 H18 0.9300 . ?
C18 C17 1.3900 . ?

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 O2 C16 104.5(2) . . ?
C1 N1 C8 111.3(2) . . ?
C1 N1 C15 122.4(3) . . ?
C15 N1 C8 108.2(2) . . ?
O1 C1 N1 124.8(3) . . ?
O1 C1 C2 128.9(3) . . ?
N1 C1 C2 106.3(2) . . ?
C5 C6 H6 120.0 . . ?
C5 C6 C7 120.0 . . ?
C7 C6 H6 120.0 . . ?
C6 C5 H5 120.0 . . ?
C4 C5 C6 120.0 . . ?
C4 C5 H5 120.0 . . ?
C5 C4 H4 120.0 . . ?
C5 C4 C3 120.0 . . ?
C3 C4 H4 120.0 . . ?
C4 C3 H3 120.0 . . ?
C4 C3 C2 120.0 . . ?
C2 C3 H3 120.0 . . ?
C3 C2 C1 130.73(18) . . ?
C7 C2 C1 109.25(18) . . ?
C7 C2 C3 120.0 . . ?
C6 C7 C8 131.51(17) . . ?
C2 C7 C6 120.0 . . ?
C2 C7 C8 108.47(17) . . ?
O2 C8 N1 103.3(2) . . ?
O2 C8 C7 112.0(2) . . ?
O2 C8 C9 110.5(2) . . ?
N1 C8 C7 103.1(2) . . ?
N1 C8 C9 113.1(3) . . ?
C7 C8 C9 114.1(2) . . ?
C10 C11 H11 120.0 . . ?
C10 C11 C12 120.0 . . ?
C12 C11 H11 120.0 . . ?
C11 C10 H10 120.0 . . ?
C9 C10 C11 120.0 . . ?
C9 C10 H10 120.0 . . ?
C10 C9 C8 121.8(2) . . ?
C14 C9 C8 118.2(2) . . ?
C14 C9 C10 120.0 . . ?
C9 C14 H14 120.0 . . ?
C9 C14 C13 120.0 . . ?
C13 C14 H14 120.0 . . ?
C14 C13 H13 120.0 . . ?
C12 C13 C14 120.0 . . ?
C12 C13 H13 120.0 . . ?
C11 C12 H12 120.0 . . ?
C13 C12 C11 120.0 . . ?
C13 C12 H12 120.0 . . ?
N1 C15 H15A 111.2 . . ?
N1 C15 H15B 111.2 . . ?
N1 C15 C16 102.9(2) . . ?
H15A C15 H15B 109.1 . . ?
C16 C15 H15A 111.2 . . ?
C16 C15 H15B 111.2 . . ?
O2 C16 C15 104.3(2) . . ?
O2 C16 H16 109.2 . . ?
O2 C16 C17 110.1(2) . . ?
C15 C16 H16 109.2 . . ?
C17 C16 C15 114.6(2) . . ?
C17 C16 H16 109.2 . . ?
C21 C22 H22 120.0 . . ?
C21 C22 C17 120.0 . . ?
C17 C22 H22 120.0 . . ?
C22 C21 H21 120.0 . . ?
C22 C21 C20 120.0 . . ?
C20 C21 H21 120.0 . . ?
C21 C20 H20 120.0 . . ?
C19 C20 C21 120.0 . . ?
C19 C20 H20 120.0 . . ?
C20 C19 H19 120.0 . . ?
C20 C19 C18 120.0 . . ?
C18 C19 H19 120.0 . . ?
C19 C18 H18 120.0 . . ?
C17 C18 C19 120.0 . . ?
C17 C18 H18 120.0 . . ?
C22 C17 C16 121.30(19) . . ?
C18 C17 C16 118.57(19) . . ?
C18 C17 C22 120.0 . . ?

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
O1 C1 C2 C3 -8.9(5) . . . . ?
O1 C1 C2 C7 169.2(3) . . . . ?
O2 C8 C9 C10 137.5(2) . . . . ?
O2 C8 C9 C14 -41.5(3) . . . . ?
O2 C16 C17 C22 34.5(3) . . . . ?
O2 C16 C17 C18 -149.80(18) . . . . ?
N1 C1 C2 C3 172.28(17) . . . . ?
N1 C1 C2 C7 -9.6(3) . . . . ?
N1 C8 C9 C10 22.2(3) . . . . ?
N1 C8 C9 C14 -156.76(18) . . . . ?
N1 C15 C16 O2 15.9(3) . . . . ?
N1 C15 C16 C17 136.3(3) . . . . ?
C1 N1 C8 O2 105.8(3) . . . . ?
C1 N1 C8 C7 -10.9(3) . . . . ?
C1 N1 C8 C9 -134.7(2) . . . . ?
C1 N1 C15 C16 -122.3(3) . . . . ?
C1 C2 C7 C6 -178.4(2) . . . . ?
C1 C2 C7 C8 2.8(2) . . . . ?
C6 C5 C4 C3 0.0 . . . . ?
C6 C7 C8 O2 75.5(3) . . . . ?
C6 C7 C8 N1 -174.08(18) . . . . ?
C6 C7 C8 C9 -51.0(3) . . . . ?
C5 C6 C7 C2 0.0 . . . . ?
C5 C6 C7 C8 178.5(2) . . . . ?
C5 C4 C3 C2 0.0 . . . . ?
C4 C3 C2 C1 178.0(3) . . . . ?
C4 C3 C2 C7 0.0 . . . . ?
C3 C2 C7 C6 0.0 . . . . ?
C3 C2 C7 C8 -178.8(2) . . . . ?
C2 C7 C8 O2 -105.9(2) . . . . ?
C2 C7 C8 N1 4.6(2) . . . . ?
C2 C7 C8 C9 127.6(2) . . . . ?
C7 C6 C5 C4 0.0 . . . . ?
C7 C8 C9 C10 -95.2(2) . . . . ?
C7 C8 C9 C14 85.8(2) . . . . ?
C8 O2 C16 C15 -35.8(3) . . . . ?
C8 O2 C16 C17 -159.1(2) . . . . ?
C8 N1 C1 O1 -166.1(3) . . . . ?
C8 N1 C1 C2 12.8(3) . . . . ?
C8 N1 C15 C16 9.2(3) . . . . ?
C8 C9 C14 C13 179.0(2) . . . . ?
C11 C10 C9 C8 -179.0(2) . . . . ?
C11 C10 C9 C14 0.0 . . . . ?
C10 C11 C12 C13 0.0 . . . . ?
C10 C9 C14 C13 0.0 . . . . ?
C9 C14 C13 C12 0.0 . . . . ?
C14 C13 C12 C11 0.0 . . . . ?
C12 C11 C10 C9 0.0 . . . . ?
C15 N1 C1 O1 -35.8(5) . . . . ?
C15 N1 C1 C2 143.0(3) . . . . ?
C15 N1 C8 O2 -31.4(3) . . . . ?
C15 N1 C8 C7 -148.2(2) . . . . ?
C15 N1 C8 C9 88.1(3) . . . . ?
C15 C16 C17 C22 -82.7(3) . . . . ?
C15 C16 C17 C18 93.1(3) . . . . ?
C16 O2 C8 N1 41.6(3) . . . . ?
C16 O2 C8 C7 151.8(2) . . . . ?
C16 O2 C8 C9 -79.7(3) . . . . ?
C22 C21 C20 C19 0.0 . . . . ?
C21 C22 C17 C16 175.7(2) . . . . ?
C21 C22 C17 C18 0.0 . . . . ?
C21 C20 C19 C18 0.0 . . . . ?
C20 C19 C18 C17 0.0 . . . . ?
C19 C18 C17 C16 -175.8(2) . . . . ?
C19 C18 C17 C22 0.0 . . . . ?
C17 C22 C21 C20 0.0 . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_site                            XU
