# Supplementary Information (SI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_SPA936
_database_code_depnum_ccdc_archive 'CCDC 2371450'
loop_
_audit_author_name
_audit_author_address
'Dohyun Moon'
;Pohang Accelerator Laboratory
South Korea
;
_audit_update_record             
;
2024-07-18 deposited with the CCDC.	2024-08-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H15 N3 O'
_chemical_formula_sum            'C23 H15 N3 O'
_chemical_formula_weight         349.38

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0021 0.0012 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0044 0.0025 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0080 0.0047 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   7.7540(16)
_cell_length_b                   9.5060(19)
_cell_length_c                   24.648(5)
_cell_angle_alpha                90
_cell_angle_beta                 96.48(3)
_cell_angle_gamma                90
_cell_volume                     1805.2(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    221(2)
_cell_measurement_reflns_used    50061
_cell_measurement_theta_min      0.361
_cell_measurement_theta_max      30.000

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.286
_exptl_crystal_F_000             728
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.051
_exptl_crystal_size_mid          0.041
_exptl_crystal_size_min          0.012
_exptl_absorpt_coefficient_mu    0.063
_shelx_estimated_absorpt_T_min   0.997
_shelx_estimated_absorpt_T_max   0.999
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.964
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
'HKL3000sm Scalepack(Otwinowski et.al,2003)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      221(2)
_diffrn_radiation_wavelength     0.630
_diffrn_radiation_type           synchrotron
_diffrn_source                   'PLSII 2D bending magnet'
_diffrn_measurement_device_type  'Rayonix SX165 CCD area detector'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18089
_diffrn_reflns_av_unetI/netI     0.0731
_diffrn_reflns_av_R_equivalents  0.0861
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_theta_min         2.037
_diffrn_reflns_theta_max         25.998
_diffrn_reflns_theta_full        22.210
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             5018
_reflns_number_gt                3171
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       
'PAL BL2D-SMDC Program(Shin et.al, 2016)'
_computing_cell_refinement       'HKL3000sm(Otwinowski & Minor, 1997)'
_computing_data_reduction        'HKL3000sm(Otwinowski & Minor, 1997)'
_computing_structure_solution    'SHELXT-2018(Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018(Sheldrick, 2018)'
_computing_molecular_graphics    'DIAMOND 4(Putx&Brandenburg, 2014)'
_computing_publication_material  'publCIF(Westrip, 2010)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0556P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5018
_refine_ls_number_parameters     245
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0916
_refine_ls_R_factor_gt           0.0530
_refine_ls_wR_factor_ref         0.1311
_refine_ls_wR_factor_gt          0.1165
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_restrained_S_all      1.008
_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 1.13975(18) 0.25163(13) 0.24956(6) 0.0489(4) Uani 1 1 d . . . . .
N1 N 0.84952(18) 0.60987(13) 0.34662(5) 0.0299(3) Uani 1 1 d . . . . .
N2 N 0.4669(3) 0.8860(2) 0.56743(8) 0.0677(6) Uani 1 1 d . . . . .
N3 N -0.0200(2) 0.66129(16) 0.56146(7) 0.0471(4) Uani 1 1 d . . . . .
C1 C 0.3799(2) 0.80263(18) 0.54499(7) 0.0400(4) Uani 1 1 d . . . . .
C2 C 0.1070(2) 0.67698(17) 0.54250(7) 0.0356(4) Uani 1 1 d . . . . .
C3 C 0.2672(2) 0.69711(16) 0.51865(6) 0.0308(3) Uani 1 1 d . . . . .
C4 C 0.2998(2) 0.61764(16) 0.47559(6) 0.0303(3) Uani 1 1 d . . . . .
H4 H 0.212975 0.551434 0.464408 0.036 Uiso 1 1 calc R U . . .
C5 C 0.7067(2) 0.59707(15) 0.37507(6) 0.0269(3) Uani 1 1 d . . . . .
C6 C 0.5688(2) 0.50296(16) 0.36754(7) 0.0342(4) Uani 1 1 d . . . . .
H6 H 0.563089 0.434148 0.340006 0.041 Uiso 1 1 calc R U . . .
C7 C 0.4409(2) 0.51403(16) 0.40182(7) 0.0331(3) Uani 1 1 d . . . . .
H7 H 0.346913 0.451064 0.397309 0.040 Uiso 1 1 calc R U . . .
C8 C 0.4457(2) 0.61676(15) 0.44362(6) 0.0277(3) Uani 1 1 d . . . . .
C9 C 0.5856(2) 0.71056(15) 0.45058(6) 0.0269(3) Uani 1 1 d . . . . .
H9 H 0.591158 0.779387 0.478106 0.032 Uiso 1 1 calc R U . . .
C10 C 0.7162(2) 0.70114(14) 0.41645(6) 0.0248(3) Uani 1 1 d . . . . .
C11 C 0.87174(19) 0.78211(15) 0.41147(6) 0.0250(3) Uani 1 1 d . . . . .
C12 C 0.9459(2) 0.90087(15) 0.43765(6) 0.0301(3) Uani 1 1 d . . . . .
H12 H 0.893774 0.943867 0.466027 0.036 Uiso 1 1 calc R U . . .
C13 C 1.0981(2) 0.95483(17) 0.42119(7) 0.0351(4) Uani 1 1 d . . . . .
H13 H 1.148969 1.035155 0.438541 0.042 Uiso 1 1 calc R U . . .
C14 C 1.1765(2) 0.89108(17) 0.37909(7) 0.0361(4) Uani 1 1 d . . . . .
H14 H 1.280952 0.928257 0.369280 0.043 Uiso 1 1 calc R U . . .
C15 C 1.1043(2) 0.77481(16) 0.35155(6) 0.0324(3) Uani 1 1 d . . . . .
H15 H 1.156301 0.733133 0.322873 0.039 Uiso 1 1 calc R U . . .
C16 C 0.9514(2) 0.72221(15) 0.36814(6) 0.0268(3) Uani 1 1 d . . . . .
C17 C 0.8764(2) 0.53576(16) 0.29742(6) 0.0294(3) Uani 1 1 d . . . . .
C18 C 0.9978(2) 0.42893(15) 0.30032(6) 0.0285(3) Uani 1 1 d . . . . .
H18 H 1.059371 0.403135 0.333885 0.034 Uiso 1 1 calc R U . . .
C19 C 1.0266(2) 0.36028(15) 0.25210(7) 0.0311(3) Uani 1 1 d . . . . .
C20 C 0.9342(2) 0.39892(17) 0.20292(7) 0.0382(4) Uani 1 1 d . . . . .
H20 H 0.954686 0.352778 0.170535 0.046 Uiso 1 1 calc R U . . .
C21 C 0.8135(3) 0.5037(2) 0.20139(7) 0.0511(5) Uani 1 1 d . . . . .
H21 H 0.749797 0.528132 0.168001 0.061 Uiso 1 1 calc R U . . .
C22 C 0.7838(3) 0.5747(2) 0.24885(8) 0.0501(5) Uani 1 1 d . . . . .
H22 H 0.702074 0.647958 0.247723 0.060 Uiso 1 1 calc R U . . .
C23 C 1.2332(4) 0.2042(2) 0.29927(11) 0.0736(8) Uani 1 1 d . . . . .
H23A H 1.307220 0.125963 0.291779 0.110 Uiso 1 1 calc R U . . .
H23B H 1.152056 0.174074 0.324132 0.110 Uiso 1 1 calc R U . . .
H23C H 1.304074 0.280426 0.315755 0.110 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 C19 1.3610(19) . ?
O1 C23 1.425(3) . ?
N1 C5 1.381(2) . ?
N1 C16 1.397(2) . ?
N1 C17 1.4380(18) . ?
N2 C1 1.142(2) . ?
N3 C2 1.147(2) . ?
C1 C3 1.436(2) . ?
C2 C3 1.445(2) . ?
C3 C4 1.350(2) . ?
C4 C8 1.450(2) . ?
C4 H4 0.9400 . ?
C5 C6 1.391(2) . ?
C5 C10 1.4169(19) . ?
C6 C7 1.378(2) . ?
C6 H6 0.9400 . ?
C7 C8 1.417(2) . ?
C7 H7 0.9400 . ?
C8 C9 1.400(2) . ?
C9 C10 1.391(2) . ?
C9 H9 0.9400 . ?
C10 C11 1.447(2) . ?
C11 C12 1.392(2) . ?
C11 C16 1.4125(19) . ?
C12 C13 1.388(2) . ?
C12 H12 0.9400 . ?
C13 C14 1.399(2) . ?
C13 H13 0.9400 . ?
C14 C15 1.382(2) . ?
C14 H14 0.9400 . ?
C15 C16 1.390(2) . ?
C15 H15 0.9400 . ?
C17 C22 1.375(2) . ?
C17 C18 1.381(2) . ?
C18 C19 1.396(2) . ?
C18 H18 0.9400 . ?
C19 C20 1.386(2) . ?
C20 C21 1.364(3) . ?
C20 H20 0.9400 . ?
C21 C22 1.392(2) . ?
C21 H21 0.9400 . ?
C22 H22 0.9400 . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C23 H23C 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
C19 O1 C23 117.94(14) . . ?
C5 N1 C16 109.03(12) . . ?
C5 N1 C17 125.85(13) . . ?
C16 N1 C17 124.43(13) . . ?
N2 C1 C3 177.80(19) . . ?
N3 C2 C3 179.9(2) . . ?
C4 C3 C1 126.01(15) . . ?
C4 C3 C2 119.45(15) . . ?
C1 C3 C2 114.53(14) . . ?
C3 C4 C8 131.12(15) . . ?
C3 C4 H4 114.4 . . ?
C8 C4 H4 114.4 . . ?
N1 C5 C6 129.60(13) . . ?
N1 C5 C10 108.93(13) . . ?
C6 C5 C10 121.46(14) . . ?
C7 C6 C5 117.72(14) . . ?
C7 C6 H6 121.1 . . ?
C5 C6 H6 121.1 . . ?
C6 C7 C8 122.48(14) . . ?
C6 C7 H7 118.8 . . ?
C8 C7 H7 118.8 . . ?
C9 C8 C7 118.98(14) . . ?
C9 C8 C4 124.82(13) . . ?
C7 C8 C4 116.19(14) . . ?
C10 C9 C8 119.48(13) . . ?
C10 C9 H9 120.3 . . ?
C8 C9 H9 120.3 . . ?
C9 C10 C5 119.88(13) . . ?
C9 C10 C11 133.46(13) . . ?
C5 C10 C11 106.63(12) . . ?
C12 C11 C16 118.97(14) . . ?
C12 C11 C10 134.15(13) . . ?
C16 C11 C10 106.82(13) . . ?
C13 C12 C11 118.97(14) . . ?
C13 C12 H12 120.5 . . ?
C11 C12 H12 120.5 . . ?
C12 C13 C14 120.77(15) . . ?
C12 C13 H13 119.6 . . ?
C14 C13 H13 119.6 . . ?
C15 C14 C13 121.67(16) . . ?
C15 C14 H14 119.2 . . ?
C13 C14 H14 119.2 . . ?
C14 C15 C16 117.06(14) . . ?
C14 C15 H15 121.5 . . ?
C16 C15 H15 121.5 . . ?
C15 C16 N1 128.90(13) . . ?
C15 C16 C11 122.52(14) . . ?
N1 C16 C11 108.57(13) . . ?
C22 C17 C18 121.92(14) . . ?
C22 C17 N1 119.43(14) . . ?
C18 C17 N1 118.63(14) . . ?
C17 C18 C19 118.26(15) . . ?
C17 C18 H18 120.9 . . ?
C19 C18 H18 120.9 . . ?
O1 C19 C20 115.68(14) . . ?
O1 C19 C18 124.05(16) . . ?
C20 C19 C18 120.25(15) . . ?
C21 C20 C19 120.20(15) . . ?
C21 C20 H20 119.9 . . ?
C19 C20 H20 119.9 . . ?
C20 C21 C22 120.58(17) . . ?
C20 C21 H21 119.7 . . ?
C22 C21 H21 119.7 . . ?
C17 C22 C21 118.78(17) . . ?
C17 C22 H22 120.6 . . ?
C21 C22 H22 120.6 . . ?
O1 C23 H23A 109.5 . . ?
O1 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
O1 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C3 C4 C8 -2.1(3) . . . . ?
C2 C3 C4 C8 178.91(15) . . . . ?
C16 N1 C5 C6 178.52(16) . . . . ?
C17 N1 C5 C6 7.8(3) . . . . ?
C16 N1 C5 C10 -0.91(17) . . . . ?
C17 N1 C5 C10 -171.65(14) . . . . ?
N1 C5 C6 C7 -179.43(15) . . . . ?
C10 C5 C6 C7 -0.1(2) . . . . ?
C5 C6 C7 C8 0.1(2) . . . . ?
C6 C7 C8 C9 -0.1(2) . . . . ?
C6 C7 C8 C4 178.59(15) . . . . ?
C3 C4 C8 C9 -3.7(3) . . . . ?
C3 C4 C8 C7 177.65(17) . . . . ?
C7 C8 C9 C10 0.1(2) . . . . ?
C4 C8 C9 C10 -178.54(14) . . . . ?
C8 C9 C10 C5 0.0(2) . . . . ?
C8 C9 C10 C11 177.66(15) . . . . ?
N1 C5 C10 C9 179.48(13) . . . . ?
C6 C5 C10 C9 0.0(2) . . . . ?
N1 C5 C10 C11 1.25(16) . . . . ?
C6 C5 C10 C11 -178.24(14) . . . . ?
C9 C10 C11 C12 -2.1(3) . . . . ?
C5 C10 C11 C12 175.82(16) . . . . ?
C9 C10 C11 C16 -179.00(16) . . . . ?
C5 C10 C11 C16 -1.11(16) . . . . ?
C16 C11 C12 C13 -1.5(2) . . . . ?
C10 C11 C12 C13 -178.11(16) . . . . ?
C11 C12 C13 C14 -0.2(2) . . . . ?
C12 C13 C14 C15 1.5(3) . . . . ?
C13 C14 C15 C16 -1.1(2) . . . . ?
C14 C15 C16 N1 177.93(16) . . . . ?
C14 C15 C16 C11 -0.7(2) . . . . ?
C5 N1 C16 C15 -178.55(15) . . . . ?
C17 N1 C16 C15 -7.7(3) . . . . ?
C5 N1 C16 C11 0.19(17) . . . . ?
C17 N1 C16 C11 171.09(14) . . . . ?
C12 C11 C16 C15 1.9(2) . . . . ?
C10 C11 C16 C15 179.42(14) . . . . ?
C12 C11 C16 N1 -176.90(13) . . . . ?
C10 C11 C16 N1 0.58(17) . . . . ?
C5 N1 C17 C22 74.3(2) . . . . ?
C16 N1 C17 C22 -95.1(2) . . . . ?
C5 N1 C17 C18 -107.09(18) . . . . ?
C16 N1 C17 C18 83.5(2) . . . . ?
C22 C17 C18 C19 0.4(2) . . . . ?
N1 C17 C18 C19 -178.16(14) . . . . ?
C23 O1 C19 C20 -177.67(18) . . . . ?
C23 O1 C19 C18 0.6(3) . . . . ?
C17 C18 C19 O1 -178.56(15) . . . . ?
C17 C18 C19 C20 -0.4(2) . . . . ?
O1 C19 C20 C21 177.91(17) . . . . ?
C18 C19 C20 C21 -0.4(3) . . . . ?
C19 C20 C21 C22 1.2(3) . . . . ?
C18 C17 C22 C21 0.2(3) . . . . ?
N1 C17 C22 C21 178.85(18) . . . . ?
C20 C21 C22 C17 -1.1(3) . . . . ?

_refine_diff_density_max         0.268
_refine_diff_density_min         -0.219
_refine_diff_density_rms         0.049























####################################################################### 
# 
# 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_SPA937
_database_code_depnum_ccdc_archive 'CCDC 2371451'
loop_
_audit_author_name
_audit_author_address
'Dohyun Moon'
;Pohang Accelerator Laboratory
South Korea
;
_audit_update_record             
;
2024-07-18 deposited with the CCDC.	2024-08-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C25 H20 N2 O3'
_chemical_formula_sum            'C25 H20 N2 O3'
_chemical_formula_weight         396.43

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0021 0.0012 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0044 0.0025 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0080 0.0047 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   17.950(4)
_cell_length_b                   18.111(4)
_cell_length_c                   14.354(3)
_cell_angle_alpha                90
_cell_angle_beta                 123.79(3)
_cell_angle_gamma                90
_cell_volume                     3877.9(18)
_cell_formula_units_Z            8
_cell_measurement_temperature    220(2)
_cell_measurement_reflns_used    57480
_cell_measurement_theta_min      0.361
_cell_measurement_theta_max      30.000

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.358
_exptl_crystal_F_000             1664
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.051
_exptl_crystal_size_mid          0.038
_exptl_crystal_size_min          0.029
_exptl_absorpt_coefficient_mu    0.070
_shelx_estimated_absorpt_T_min   0.996
_shelx_estimated_absorpt_T_max   0.998
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.980
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
'HKL3000sm Scalepack(Otwinowski et.al,2003)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      220(2)
_diffrn_radiation_wavelength     0.630
_diffrn_radiation_type           synchrotron
_diffrn_source                   'PLSII 2D bending magnet'
_diffrn_measurement_device_type  'Rayonix SX165 CCD area detector'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20192
_diffrn_reflns_av_unetI/netI     0.0430
_diffrn_reflns_av_R_equivalents  0.0549
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.568
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_full        22.210
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measured_fraction_theta_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_point_group_measured_fraction_full 0.977
_reflns_number_total             5296
_reflns_number_gt                3992
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       
'PAL BL2D-SMDC Program(Shin et.al, 2016)'
_computing_cell_refinement       'HKL3000sm(Otwinowski & Minor, 1997)'
_computing_data_reduction        'HKL3000sm(Otwinowski & Minor, 1997)'
_computing_structure_solution    'SHELXT-2018(Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018(Sheldrick, 2018)'
_computing_molecular_graphics    'DIAMOND 4(Putx&Brandenburg, 2014)'
_computing_publication_material  'publCIF(Westrip, 2010)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0647P)²+0.7741P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_extinction_coef       0.0120(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         5296
_refine_ls_number_parameters     274
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0620
_refine_ls_R_factor_gt           0.0454
_refine_ls_wR_factor_ref         0.1241
_refine_ls_wR_factor_gt          0.1152
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.049
_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 0.54744(8) 0.07829(5) 0.49269(8) 0.0386(2) Uani 1 1 d . . . . .
O2 O 0.17619(7) 0.59846(6) 0.31678(10) 0.0435(3) Uani 1 1 d . . . . .
O3 O 0.25641(6) 0.70260(5) 0.38652(8) 0.0324(2) Uani 1 1 d . . . . .
N1 N 0.58712(7) 0.29919(5) 0.70495(8) 0.0252(2) Uani 1 1 d . . . . .
N2 N 0.46613(9) 0.67149(7) 0.59944(11) 0.0425(3) Uani 1 1 d . . . . .
C1 C 0.53568(13) 0.12101(9) 0.40341(12) 0.0479(4) Uani 1 1 d . . . . .
H1A H 0.529939 0.088641 0.345907 0.072 Uiso 1 1 calc R U . . .
H1B H 0.587117 0.153095 0.430772 0.072 Uiso 1 1 calc R U . . .
H1C H 0.481890 0.150717 0.372066 0.072 Uiso 1 1 calc R U . . .
C2 C 0.56534(8) 0.11403(6) 0.58596(10) 0.0259(2) Uani 1 1 d . . . . .
C3 C 0.56407(8) 0.19023(6) 0.59458(10) 0.0241(2) Uani 1 1 d . . . . .
H3 H 0.548300 0.220529 0.533036 0.029 Uiso 1 1 calc R U . . .
C4 C 0.58642(8) 0.22093(6) 0.69538(10) 0.0238(2) Uani 1 1 d . . . . .
C5 C 0.60993(9) 0.17745(7) 0.78669(11) 0.0287(3) Uani 1 1 d . . . . .
H5 H 0.625587 0.198980 0.854907 0.034 Uiso 1 1 calc R U . . .
C6 C 0.61004(9) 0.10126(7) 0.77601(11) 0.0309(3) Uani 1 1 d . . . . .
H6 H 0.625466 0.071041 0.837510 0.037 Uiso 1 1 calc R U . . .
C7 C 0.58793(9) 0.06933(7) 0.67678(11) 0.0306(3) Uani 1 1 d . . . . .
H7 H 0.588093 0.017684 0.670440 0.037 Uiso 1 1 calc R U . . .
C8 C 0.66144(8) 0.34152(6) 0.78083(10) 0.0236(2) Uani 1 1 d . . . . .
C9 C 0.74753(8) 0.31863(7) 0.86359(11) 0.0295(3) Uani 1 1 d . . . . .
H9 H 0.762517 0.268273 0.877052 0.035 Uiso 1 1 calc R U . . .
C10 C 0.81023(9) 0.37288(8) 0.92532(11) 0.0327(3) Uani 1 1 d . . . . .
H10 H 0.869155 0.359016 0.981546 0.039 Uiso 1 1 calc R U . . .
C11 C 0.78841(9) 0.44756(8) 0.90641(11) 0.0346(3) Uani 1 1 d . . . . .
H11 H 0.832427 0.483222 0.950125 0.042 Uiso 1 1 calc R U . . .
C12 C 0.70279(9) 0.46957(7) 0.82411(11) 0.0310(3) Uani 1 1 d . . . . .
H12 H 0.688152 0.520012 0.811369 0.037 Uiso 1 1 calc R U . . .
C13 C 0.63843(8) 0.41644(6) 0.76027(10) 0.0235(2) Uani 1 1 d . . . . .
C14 C 0.54560(8) 0.41966(6) 0.66735(10) 0.0223(2) Uani 1 1 d . . . . .
C15 C 0.48692(8) 0.47730(6) 0.61060(10) 0.0250(2) Uani 1 1 d . . . . .
H15 H 0.505919 0.526441 0.631216 0.030 Uiso 1 1 calc R U . . .
C16 C 0.39893(8) 0.46170(6) 0.52212(10) 0.0245(2) Uani 1 1 d . . . . .
C17 C 0.37261(8) 0.38720(6) 0.49313(11) 0.0268(3) Uani 1 1 d . . . . .
H17 H 0.313357 0.376976 0.433749 0.032 Uiso 1 1 calc R U . . .
C18 C 0.42997(8) 0.32921(6) 0.54805(10) 0.0266(3) Uani 1 1 d . . . . .
H18 H 0.411164 0.280066 0.527139 0.032 Uiso 1 1 calc R U . . .
C19 C 0.51699(8) 0.34604(6) 0.63585(10) 0.0227(2) Uani 1 1 d . . . . .
C20 C 0.33057(9) 0.51619(7) 0.45735(11) 0.0272(2) Uani 1 1 d . . . . .
H20 H 0.274945 0.496075 0.401263 0.033 Uiso 1 1 calc R U . . .
C21 C 0.33121(8) 0.59067(7) 0.46189(10) 0.0261(2) Uani 1 1 d . . . . .
C22 C 0.40658(9) 0.63490(7) 0.53817(11) 0.0290(3) Uani 1 1 d . . . . .
C23 C 0.24576(9) 0.62944(7) 0.38005(11) 0.0288(3) Uani 1 1 d . . . . .
C24 C 0.17584(9) 0.74455(7) 0.30901(13) 0.0353(3) Uani 1 1 d . . . . .
H24A H 0.131981 0.739307 0.328899 0.042 Uiso 1 1 calc R U . . .
H24B H 0.148732 0.726349 0.232364 0.042 Uiso 1 1 calc R U . . .
C25 C 0.20220(10) 0.82363(7) 0.31667(14) 0.0408(3) Uani 1 1 d . . . . .
H25A H 0.149137 0.853288 0.268545 0.061 Uiso 1 1 calc R U . . .
H25B H 0.243057 0.828580 0.292897 0.061 Uiso 1 1 calc R U . . .
H25C H 0.231516 0.840402 0.393549 0.061 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 C2 1.3550(15) . ?
O1 C1 1.4087(18) . ?
O2 C23 1.1990(17) . ?
O3 C23 1.3346(15) . ?
O3 C24 1.4548(16) . ?
N1 C19 1.3781(15) . ?
N1 C8 1.3919(16) . ?
N1 C4 1.4234(15) . ?
N2 C22 1.1443(19) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C1 H1C 0.9700 . ?
C2 C3 1.3869(16) . ?
C2 C7 1.3896(17) . ?
C3 C4 1.3848(17) . ?
C3 H3 0.9400 . ?
C4 C5 1.3787(17) . ?
C5 C6 1.3885(17) . ?
C5 H5 0.9400 . ?
C6 C7 1.3753(19) . ?
C6 H6 0.9400 . ?
C7 H7 0.9400 . ?
C8 C9 1.3890(18) . ?
C8 C13 1.4011(16) . ?
C9 C10 1.3811(18) . ?
C9 H9 0.9400 . ?
C10 C11 1.392(2) . ?
C10 H10 0.9400 . ?
C11 C12 1.377(2) . ?
C11 H11 0.9400 . ?
C12 C13 1.3865(17) . ?
C12 H12 0.9400 . ?
C13 C14 1.4445(18) . ?
C14 C15 1.3814(16) . ?
C14 C19 1.4098(15) . ?
C15 C16 1.3986(18) . ?
C15 H15 0.9400 . ?
C16 C17 1.4136(16) . ?
C16 C20 1.4404(16) . ?
C17 C18 1.3717(16) . ?
C17 H17 0.9400 . ?
C18 C19 1.3897(18) . ?
C18 H18 0.9400 . ?
C20 C21 1.3502(17) . ?
C20 H20 0.9400 . ?
C21 C22 1.4224(19) . ?
C21 C23 1.4903(18) . ?
C24 C25 1.4930(19) . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?
C25 H25C 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
C2 O1 C1 118.02(11) . . ?
C23 O3 C24 114.98(10) . . ?
C19 N1 C8 108.56(10) . . ?
C19 N1 C4 126.02(10) . . ?
C8 N1 C4 125.25(10) . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C2 C3 123.84(11) . . ?
O1 C2 C7 115.71(11) . . ?
C3 C2 C7 120.44(11) . . ?
C4 C3 C2 118.89(11) . . ?
C4 C3 H3 120.6 . . ?
C2 C3 H3 120.6 . . ?
C5 C4 C3 121.44(11) . . ?
C5 C4 N1 119.70(11) . . ?
C3 C4 N1 118.85(10) . . ?
C4 C5 C6 118.75(12) . . ?
C4 C5 H5 120.6 . . ?
C6 C5 H5 120.6 . . ?
C7 C6 C5 120.99(11) . . ?
C7 C6 H6 119.5 . . ?
C5 C6 H6 119.5 . . ?
C6 C7 C2 119.49(11) . . ?
C6 C7 H7 120.3 . . ?
C2 C7 H7 120.3 . . ?
C9 C8 N1 129.13(11) . . ?
C9 C8 C13 121.77(11) . . ?
N1 C8 C13 109.06(10) . . ?
C10 C9 C8 117.28(12) . . ?
C10 C9 H9 121.4 . . ?
C8 C9 H9 121.4 . . ?
C9 C10 C11 121.70(13) . . ?
C9 C10 H10 119.1 . . ?
C11 C10 H10 119.1 . . ?
C12 C11 C10 120.47(12) . . ?
C12 C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?
C11 C12 C13 119.22(12) . . ?
C11 C12 H12 120.4 . . ?
C13 C12 H12 120.4 . . ?
C12 C13 C8 119.55(12) . . ?
C12 C13 C14 133.75(11) . . ?
C8 C13 C14 106.68(10) . . ?
C15 C14 C19 120.22(11) . . ?
C15 C14 C13 133.20(11) . . ?
C19 C14 C13 106.58(10) . . ?
C14 C15 C16 119.23(11) . . ?
C14 C15 H15 120.4 . . ?
C16 C15 H15 120.4 . . ?
C15 C16 C17 118.94(10) . . ?
C15 C16 C20 125.04(11) . . ?
C17 C16 C20 116.02(11) . . ?
C18 C17 C16 122.72(12) . . ?
C18 C17 H17 118.6 . . ?
C16 C17 H17 118.6 . . ?
C17 C18 C19 117.33(11) . . ?
C17 C18 H18 121.3 . . ?
C19 C18 H18 121.3 . . ?
N1 C19 C18 129.33(11) . . ?
N1 C19 C14 109.11(10) . . ?
C18 C19 C14 121.56(10) . . ?
C21 C20 C16 132.22(12) . . ?
C21 C20 H20 113.9 . . ?
C16 C20 H20 113.9 . . ?
C20 C21 C22 125.36(12) . . ?
C20 C21 C23 117.08(12) . . ?
C22 C21 C23 117.56(11) . . ?
N2 C22 C21 178.69(14) . . ?
O2 C23 O3 124.46(12) . . ?
O2 C23 C21 123.94(12) . . ?
O3 C23 C21 111.60(11) . . ?
O3 C24 C25 107.77(11) . . ?
O3 C24 H24A 110.2 . . ?
C25 C24 H24A 110.2 . . ?
O3 C24 H24B 110.2 . . ?
C25 C24 H24B 110.2 . . ?
H24A C24 H24B 108.5 . . ?
C24 C25 H25A 109.5 . . ?
C24 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C24 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 O1 C2 C3 6.60(19) . . . . ?
C1 O1 C2 C7 -171.88(13) . . . . ?
O1 C2 C3 C4 -177.86(12) . . . . ?
C7 C2 C3 C4 0.56(18) . . . . ?
C2 C3 C4 C5 0.15(18) . . . . ?
C2 C3 C4 N1 178.55(11) . . . . ?
C19 N1 C4 C5 -126.56(14) . . . . ?
C8 N1 C4 C5 58.69(17) . . . . ?
C19 N1 C4 C3 55.00(17) . . . . ?
C8 N1 C4 C3 -119.74(13) . . . . ?
C3 C4 C5 C6 -0.69(19) . . . . ?
N1 C4 C5 C6 -179.08(12) . . . . ?
C4 C5 C6 C7 0.5(2) . . . . ?
C5 C6 C7 C2 0.2(2) . . . . ?
O1 C2 C7 C6 177.83(12) . . . . ?
C3 C2 C7 C6 -0.71(19) . . . . ?
C19 N1 C8 C9 -177.76(13) . . . . ?
C4 N1 C8 C9 -2.2(2) . . . . ?
C19 N1 C8 C13 0.24(14) . . . . ?
C4 N1 C8 C13 175.75(11) . . . . ?
N1 C8 C9 C10 177.67(13) . . . . ?
C13 C8 C9 C10 -0.11(19) . . . . ?
C8 C9 C10 C11 0.4(2) . . . . ?
C9 C10 C11 C12 -0.4(2) . . . . ?
C10 C11 C12 C13 0.1(2) . . . . ?
C11 C12 C13 C8 0.3(2) . . . . ?
C11 C12 C13 C14 -177.63(13) . . . . ?
C9 C8 C13 C12 -0.24(19) . . . . ?
N1 C8 C13 C12 -178.42(11) . . . . ?
C9 C8 C13 C14 178.17(11) . . . . ?
N1 C8 C13 C14 -0.01(14) . . . . ?
C12 C13 C14 C15 -2.0(2) . . . . ?
C8 C13 C14 C15 179.90(13) . . . . ?
C12 C13 C14 C19 177.87(14) . . . . ?
C8 C13 C14 C19 -0.21(13) . . . . ?
C19 C14 C15 C16 0.30(18) . . . . ?
C13 C14 C15 C16 -179.83(13) . . . . ?
C14 C15 C16 C17 -0.14(18) . . . . ?
C14 C15 C16 C20 178.82(11) . . . . ?
C15 C16 C17 C18 -0.19(19) . . . . ?
C20 C16 C17 C18 -179.24(12) . . . . ?
C16 C17 C18 C19 0.34(19) . . . . ?
C8 N1 C19 C18 -179.92(13) . . . . ?
C4 N1 C19 C18 4.6(2) . . . . ?
C8 N1 C19 C14 -0.38(14) . . . . ?
C4 N1 C19 C14 -175.85(11) . . . . ?
C17 C18 C19 N1 179.32(12) . . . . ?
C17 C18 C19 C14 -0.18(18) . . . . ?
C15 C14 C19 N1 -179.73(11) . . . . ?
C13 C14 C19 N1 0.36(13) . . . . ?
C15 C14 C19 C18 -0.14(18) . . . . ?
C13 C14 C19 C18 179.95(11) . . . . ?
C15 C16 C20 C21 0.4(2) . . . . ?
C17 C16 C20 C21 179.41(13) . . . . ?
C16 C20 C21 C22 0.4(2) . . . . ?
C16 C20 C21 C23 -179.61(13) . . . . ?
C24 O3 C23 O2 -0.36(19) . . . . ?
C24 O3 C23 C21 179.95(11) . . . . ?
C20 C21 C23 O2 5.3(2) . . . . ?
C22 C21 C23 O2 -174.71(13) . . . . ?
C20 C21 C23 O3 -175.00(11) . . . . ?
C22 C21 C23 O3 4.98(16) . . . . ?
C23 O3 C24 C25 -172.52(12) . . . . ?

_refine_diff_density_max         0.286
_refine_diff_density_min         -0.281
_refine_diff_density_rms         0.053























####################################################################### 
# 
# 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_SPA939_sq
_database_code_depnum_ccdc_archive 'CCDC 2371452'
loop_
_audit_author_name
_audit_author_address
'Dohyun Moon'
;Pohang Accelerator Laboratory
South Korea
;
_audit_update_record             
;
2024-07-18 deposited with the CCDC.	2024-08-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H17 N3 O2'
_chemical_formula_sum            'C23 H17 N3 O2'
_chemical_formula_weight         367.39

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0021 0.0012 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0044 0.0025 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0080 0.0047 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   12.001(2)
_cell_length_b                   12.848(3)
_cell_length_c                   15.283(3)
_cell_angle_alpha                67.14(3)
_cell_angle_beta                 84.08(3)
_cell_angle_gamma                70.78(3)
_cell_volume                     2049.5(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    221(2)
_cell_measurement_reflns_used    116326
_cell_measurement_theta_min      0.361
_cell_measurement_theta_max      30.000

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.191
_exptl_crystal_F_000             768
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.031
_exptl_crystal_size_mid          0.025
_exptl_crystal_size_min          0.021
_exptl_absorpt_coefficient_mu    0.061
_shelx_estimated_absorpt_T_min   0.998
_shelx_estimated_absorpt_T_max   0.999
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.914
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
'HKL3000sm Scalepack(Otwinowski et.al,2003)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      221(2)
_diffrn_radiation_wavelength     0.630
_diffrn_radiation_type           synchrotron
_diffrn_source                   'PLSII 2D bending magnet'
_diffrn_measurement_device_type  'Rayonix MX225HS CCD area detector'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            23018
_diffrn_reflns_av_unetI/netI     0.0826
_diffrn_reflns_av_R_equivalents  0.0502
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.594
_diffrn_reflns_theta_max         26.000
_diffrn_reflns_theta_full        22.210
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             11512
_reflns_number_gt                4584
_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.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       
'PAL BL2D-SMDC Program(Shin et.al, 2016)'
_computing_cell_refinement       'HKL3000sm(Otwinowski & Minor, 1997)'
_computing_data_reduction        'HKL3000sm(Otwinowski & Minor, 1997)'
_computing_structure_solution    'SHELXT-2018(Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018(Sheldrick, 2018)'
_computing_molecular_graphics    'DIAMOND 4(Putx&Brandenburg, 2014)'
_computing_publication_material  'publCIF(Westrip, 2010)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1362P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_extinction_coef       0.044(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         11512
_refine_ls_number_parameters     508
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1592
_refine_ls_R_factor_gt           0.0735
_refine_ls_wR_factor_ref         0.2533
_refine_ls_wR_factor_gt          0.2089
_refine_ls_goodness_of_fit_ref   0.916
_refine_ls_restrained_S_all      0.916
_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
O1A O -0.3905(2) 0.13832(18) 1.2998(2) 0.1016(9) Uani 1 1 d . . . . .
O2A O 0.43199(17) 0.54111(16) 0.90188(13) 0.0617(5) Uani 1 1 d . . . . .
N1A N -0.12139(19) 0.35948(19) 1.23122(15) 0.0552(5) Uani 1 1 d . . . . .
N2A N 0.4660(3) 0.1520(3) 1.1007(2) 0.0952(10) Uani 1 1 d . . . . .
N3A N 0.5615(2) 0.3608(2) 0.92729(18) 0.0682(7) Uani 1 1 d . . . . .
H3AA H 0.612071 0.389851 0.888883 0.082 Uiso 1 1 calc R U . . .
H3AB H 0.577939 0.284166 0.956672 0.082 Uiso 1 1 calc R U . . .
C1A C -0.4137(4) 0.0273(3) 1.3397(4) 0.1138(16) Uani 1 1 d . . . . .
H1AA H -0.487337 0.035414 1.312842 0.171 Uiso 1 1 calc R U . . .
H1AB H -0.419755 0.004071 1.408020 0.171 Uiso 1 1 calc R U . . .
H1AC H -0.349899 -0.032937 1.325395 0.171 Uiso 1 1 calc R U . . .
C2A C -0.2860(3) 0.1426(3) 1.3215(2) 0.0703(8) Uani 1 1 d . . . . .
C3A C -0.2570(3) 0.2449(2) 1.2682(2) 0.0660(8) Uani 1 1 d . . . . .
H3A H -0.309018 0.307289 1.219908 0.079 Uiso 1 1 calc R U . . .
C4A C -0.1522(2) 0.2549(2) 1.28624(19) 0.0563(7) Uani 1 1 d . . . . .
C5A C -0.0759(3) 0.1631(3) 1.3547(2) 0.0842(10) Uani 1 1 d . . . . .
H5A H -0.004269 0.169715 1.367838 0.101 Uiso 1 1 calc R U . . .
C6A C -0.1041(4) 0.0607(3) 1.4045(3) 0.1044(13) Uani 1 1 d . . . . .
H6A H -0.049125 -0.004128 1.449089 0.125 Uiso 1 1 calc R U . . .
C7A C -0.2106(4) 0.0508(3) 1.3907(3) 0.0870(10) Uani 1 1 d . . . . .
H7A H -0.231152 -0.017690 1.428023 0.104 Uiso 1 1 calc R U . . .
C8A C -0.1899(2) 0.4766(2) 1.21679(18) 0.0544(6) Uani 1 1 d . . . . .
C9A C -0.3001(3) 0.5183(3) 1.2500(2) 0.0606(7) Uani 1 1 d . . . . .
H9A H -0.340677 0.466116 1.288579 0.073 Uiso 1 1 calc R U . . .
C10A C -0.3475(3) 0.6380(3) 1.2248(2) 0.0696(8) Uani 1 1 d . . . . .
H10A H -0.422610 0.668793 1.246387 0.084 Uiso 1 1 calc R U . . .
C11A C -0.2879(3) 0.7170(3) 1.1675(2) 0.0738(9) Uani 1 1 d . . . . .
H11A H -0.323805 0.799433 1.150366 0.089 Uiso 1 1 calc R U . . .
C12A C -0.1783(3) 0.6747(3) 1.1366(2) 0.0654(8) Uani 1 1 d . . . . .
H12A H -0.137385 0.727328 1.099496 0.078 Uiso 1 1 calc R U . . .
C13A C -0.1274(2) 0.5528(2) 1.16034(18) 0.0537(6) Uani 1 1 d . . . . .
C14A C -0.0177(2) 0.4805(2) 1.13891(17) 0.0516(6) Uani 1 1 d . . . . .
C15A C 0.0775(2) 0.5040(2) 1.08583(18) 0.0531(6) Uani 1 1 d . . . . .
H15A H 0.077805 0.583066 1.055689 0.064 Uiso 1 1 calc R U . . .
C16A C 0.1722(2) 0.4130(2) 1.07635(18) 0.0538(6) Uani 1 1 d . . . . .
C17A C 0.1684(3) 0.2964(2) 1.1211(2) 0.0626(7) Uani 1 1 d . . . . .
H17A H 0.232151 0.234212 1.113883 0.075 Uiso 1 1 calc R U . . .
C18A C 0.0761(3) 0.2687(2) 1.1749(2) 0.0621(7) Uani 1 1 d . . . . .
H18A H 0.076167 0.189421 1.204496 0.075 Uiso 1 1 calc R U . . .
C19A C -0.0177(2) 0.3616(2) 1.18411(18) 0.0536(6) Uani 1 1 d . . . . .
C20A C 0.2690(2) 0.4439(3) 1.01914(18) 0.0560(7) Uani 1 1 d . . . . .
H20A H 0.253095 0.525673 0.983144 0.067 Uiso 1 1 calc R U . . .
C21A C 0.3784(2) 0.3755(2) 1.00854(19) 0.0565(7) Uani 1 1 d . . . . .
C22A C 0.4603(2) 0.4328(2) 0.94095(19) 0.0538(6) Uani 1 1 d . . . . .
C23A C 0.4239(3) 0.2519(3) 1.0600(2) 0.0685(8) Uani 1 1 d . . . . .
O1B O 1.3378(3) 0.8654(2) 0.1148(2) 0.1147(10) Uani 1 1 d . . . . .
O2B O 0.72408(17) 0.45979(17) 0.80029(14) 0.0651(5) Uani 1 1 d . . . . .
N1B N 1.2383(2) 0.6352(2) 0.41988(18) 0.0651(7) Uani 1 1 d . . . . .
N2B N 0.6890(3) 0.8513(3) 0.6021(2) 0.0865(9) Uani 1 1 d . . . . .
N3B N 0.5880(2) 0.6390(2) 0.76655(17) 0.0634(6) Uani 1 1 d . . . . .
H3BA H 0.540702 0.610610 0.809307 0.076 Uiso 1 1 calc R U . . .
H3BB H 0.567723 0.714807 0.732034 0.076 Uiso 1 1 calc R U . . .
C1B C 1.3491(6) 0.9749(4) 0.0473(4) 0.153(2) Uani 1 1 d . . . . .
H1BA H 1.337348 0.980360 -0.016320 0.230 Uiso 1 1 calc R U . . .
H1BB H 1.427417 0.978141 0.053704 0.230 Uiso 1 1 calc R U . . .
H1BC H 1.290386 1.040830 0.058769 0.230 Uiso 1 1 calc R U . . .
C2B C 1.3123(3) 0.8580(3) 0.2052(3) 0.0861(11) Uani 1 1 d . . . . .
C3B C 1.2900(3) 0.7542(3) 0.2663(2) 0.0760(9) Uani 1 1 d . . . . .
H3B H 1.294497 0.694030 0.244386 0.091 Uiso 1 1 calc R U . . .
C4B C 1.2619(3) 0.7401(2) 0.3573(2) 0.0689(8) Uani 1 1 d . . . . .
C5B C 1.2562(3) 0.8277(3) 0.3918(3) 0.0768(9) Uani 1 1 d . . . . .
H5B H 1.236869 0.817345 0.455213 0.092 Uiso 1 1 calc R U . . .
C6B C 1.2794(3) 0.9292(3) 0.3314(3) 0.0885(11) Uani 1 1 d . . . . .
H6B H 1.275374 0.989085 0.353520 0.106 Uiso 1 1 calc R U . . .
C7B C 1.3086(3) 0.9446(3) 0.2381(3) 0.0876(11) Uani 1 1 d . . . . .
H7B H 1.325753 1.013822 0.197534 0.105 Uiso 1 1 calc R U . . .
C8B C 1.3185(3) 0.5208(2) 0.4494(2) 0.0578(7) Uani 1 1 d . . . . .
C9B C 1.4285(3) 0.4793(3) 0.4159(2) 0.0664(8) Uani 1 1 d . . . . .
H9B H 1.460889 0.530923 0.366344 0.080 Uiso 1 1 calc R U . . .
C10B C 1.4882(3) 0.3619(3) 0.4568(2) 0.0707(8) Uani 1 1 d . . . . .
H10B H 1.563855 0.332079 0.435576 0.085 Uiso 1 1 calc R U . . .
C11B C 1.4408(3) 0.2839(3) 0.5293(2) 0.0752(9) Uani 1 1 d . . . . .
H11B H 1.484098 0.202465 0.555222 0.090 Uiso 1 1 calc R U . . .
C12B C 1.3315(3) 0.3247(3) 0.5633(2) 0.0659(8) Uani 1 1 d . . . . .
H12B H 1.299820 0.272203 0.612773 0.079 Uiso 1 1 calc R U . . .
C13B C 1.2689(2) 0.4448(2) 0.52330(19) 0.0549(6) Uani 1 1 d . . . . .
C14B C 1.1544(2) 0.5170(2) 0.53867(19) 0.0561(7) Uani 1 1 d . . . . .
C15B C 1.0654(2) 0.4936(2) 0.60119(19) 0.0555(7) Uani 1 1 d . . . . .
H15B H 1.075571 0.416464 0.646665 0.067 Uiso 1 1 calc R U . . .
C16B C 0.9612(3) 0.5846(2) 0.59636(19) 0.0575(7) Uani 1 1 d . . . . .
C17B C 0.9475(3) 0.6979(3) 0.5265(2) 0.0661(8) Uani 1 1 d . . . . .
H17B H 0.875424 0.758579 0.521260 0.079 Uiso 1 1 calc R U . . .
C18B C 1.0352(3) 0.7238(3) 0.4653(2) 0.0706(8) Uani 1 1 d . . . . .
H18B H 1.024891 0.800710 0.419342 0.085 Uiso 1 1 calc R U . . .
C19B C 1.1395(3) 0.6322(3) 0.4739(2) 0.0614(7) Uani 1 1 d . . . . .
C20B C 0.8702(3) 0.5556(3) 0.66273(19) 0.0573(7) Uani 1 1 d . . . . .
H20B H 0.886471 0.473972 0.699447 0.069 Uiso 1 1 calc R U . . .
C21B C 0.7676(3) 0.6246(2) 0.68074(19) 0.0562(7) Uani 1 1 d . . . . .
C22B C 0.6903(3) 0.5673(3) 0.75407(19) 0.0550(7) Uani 1 1 d . . . . .
C23B C 0.7255(3) 0.7495(3) 0.6359(2) 0.0640(7) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1A C2A 1.354(4) . ?
O1A C1A 1.426(3) . ?
O2A C22A 1.222(3) . ?
N1A C19A 1.375(3) . ?
N1A C8A 1.398(3) . ?
N1A C4A 1.427(3) . ?
N2A C23A 1.144(4) . ?
N3A C22A 1.317(4) . ?
N3A H3AA 0.8700 . ?
N3A H3AB 0.8700 . ?
C1A H1AA 0.9700 . ?
C1A H1AB 0.9700 . ?
C1A H1AC 0.9700 . ?
C2A C7A 1.361(5) . ?
C2A C3A 1.387(4) . ?
C3A C4A 1.370(4) . ?
C3A H3A 0.9400 . ?
C4A C5A 1.361(4) . ?
C5A C6A 1.374(5) . ?
C5A H5A 0.9400 . ?
C6A C7A 1.370(5) . ?
C6A H6A 0.9400 . ?
C7A H7A 0.9400 . ?
C8A C9A 1.378(4) . ?
C8A C13A 1.399(3) . ?
C9A C10A 1.358(4) . ?
C9A H9A 0.9400 . ?
C10A C11A 1.403(4) . ?
C10A H10A 0.9400 . ?
C11A C12A 1.360(4) . ?
C11A H11A 0.9400 . ?
C12A C13A 1.390(4) . ?
C12A H12A 0.9400 . ?
C13A C14A 1.430(4) . ?
C14A C15A 1.378(4) . ?
C14A C19A 1.410(3) . ?
C15A C16A 1.380(4) . ?
C15A H15A 0.9400 . ?
C16A C17A 1.399(4) . ?
C16A C20A 1.448(4) . ?
C17A C18A 1.369(4) . ?
C17A H17A 0.9400 . ?
C18A C19A 1.387(4) . ?
C18A H18A 0.9400 . ?
C20A C21A 1.352(4) . ?
C20A H20A 0.9400 . ?
C21A C23A 1.409(4) . ?
C21A C22A 1.501(3) . ?
O1B C2B 1.357(4) . ?
O1B C1B 1.425(4) . ?
O2B C22B 1.226(3) . ?
N1B C19B 1.376(3) . ?
N1B C8B 1.390(4) . ?
N1B C4B 1.416(3) . ?
N2B C23B 1.146(4) . ?
N3B C22B 1.318(4) . ?
N3B H3BA 0.8700 . ?
N3B H3BB 0.8700 . ?
C1B H1BA 0.9700 . ?
C1B H1BB 0.9700 . ?
C1B H1BC 0.9700 . ?
C2B C7B 1.375(5) . ?
C2B C3B 1.392(4) . ?
C3B C4B 1.353(4) . ?
C3B H3B 0.9400 . ?
C4B C5B 1.397(4) . ?
C5B C6B 1.371(4) . ?
C5B H5B 0.9400 . ?
C6B C7B 1.385(5) . ?
C6B H6B 0.9400 . ?
C7B H7B 0.9400 . ?
C8B C9B 1.378(4) . ?
C8B C13B 1.404(4) . ?
C9B C10B 1.352(4) . ?
C9B H9B 0.9400 . ?
C10B C11B 1.393(4) . ?
C10B H10B 0.9400 . ?
C11B C12B 1.373(4) . ?
C11B H11B 0.9400 . ?
C12B C13B 1.385(4) . ?
C12B H12B 0.9400 . ?
C13B C14B 1.438(4) . ?
C14B C15B 1.386(4) . ?
C14B C19B 1.388(4) . ?
C15B C16B 1.387(4) . ?
C15B H15B 0.9400 . ?
C16B C17B 1.400(4) . ?
C16B C20B 1.451(4) . ?
C17B C18B 1.371(4) . ?
C17B H17B 0.9400 . ?
C18B C19B 1.383(4) . ?
C18B H18B 0.9400 . ?
C20B C21B 1.334(4) . ?
C20B H20B 0.9400 . ?
C21B C23B 1.409(4) . ?
C21B C22B 1.501(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
C2A O1A C1A 118.5(3) . . ?
C19A N1A C8A 108.3(2) . . ?
C19A N1A C4A 125.4(2) . . ?
C8A N1A C4A 126.3(2) . . ?
C22A N3A H3AA 120.0 . . ?
C22A N3A H3AB 120.0 . . ?
H3AA N3A H3AB 120.0 . . ?
O1A C1A H1AA 109.5 . . ?
O1A C1A H1AB 109.5 . . ?
H1AA C1A H1AB 109.5 . . ?
O1A C1A H1AC 109.5 . . ?
H1AA C1A H1AC 109.5 . . ?
H1AB C1A H1AC 109.5 . . ?
O1A C2A C7A 122.4(3) . . ?
O1A C2A C3A 116.8(3) . . ?
C7A C2A C3A 120.8(3) . . ?
C4A C3A C2A 119.8(3) . . ?
C4A C3A H3A 120.1 . . ?
C2A C3A H3A 120.1 . . ?
C5A C4A C3A 119.8(3) . . ?
C5A C4A N1A 120.1(3) . . ?
C3A C4A N1A 120.1(3) . . ?
C4A C5A C6A 119.6(3) . . ?
C4A C5A H5A 120.2 . . ?
C6A C5A H5A 120.2 . . ?
C7A C6A C5A 121.5(3) . . ?
C7A C6A H6A 119.2 . . ?
C5A C6A H6A 119.2 . . ?
C2A C7A C6A 118.3(3) . . ?
C2A C7A H7A 120.9 . . ?
C6A C7A H7A 120.9 . . ?
C9A C8A N1A 129.2(2) . . ?
C9A C8A C13A 122.3(3) . . ?
N1A C8A C13A 108.5(2) . . ?
C10A C9A C8A 117.2(3) . . ?
C10A C9A H9A 121.4 . . ?
C8A C9A H9A 121.4 . . ?
C9A C10A C11A 122.1(3) . . ?
C9A C10A H10A 119.0 . . ?
C11A C10A H10A 119.0 . . ?
C12A C11A C10A 120.2(3) . . ?
C12A C11A H11A 119.9 . . ?
C10A C11A H11A 119.9 . . ?
C11A C12A C13A 119.4(3) . . ?
C11A C12A H12A 120.3 . . ?
C13A C12A H12A 120.3 . . ?
C12A C13A C8A 118.9(3) . . ?
C12A C13A C14A 133.6(2) . . ?
C8A C13A C14A 107.5(2) . . ?
C15A C14A C19A 119.3(3) . . ?
C15A C14A C13A 134.3(2) . . ?
C19A C14A C13A 106.4(2) . . ?
C14A C15A C16A 120.9(2) . . ?
C14A C15A H15A 119.6 . . ?
C16A C15A H15A 119.6 . . ?
C15A C16A C17A 118.2(2) . . ?
C15A C16A C20A 118.1(2) . . ?
C17A C16A C20A 123.7(3) . . ?
C18A C17A C16A 123.0(3) . . ?
C18A C17A H17A 118.5 . . ?
C16A C17A H17A 118.5 . . ?
C17A C18A C19A 117.8(2) . . ?
C17A C18A H18A 121.1 . . ?
C19A C18A H18A 121.1 . . ?
N1A C19A C18A 129.8(2) . . ?
N1A C19A C14A 109.3(2) . . ?
C18A C19A C14A 120.8(2) . . ?
C21A C20A C16A 131.1(3) . . ?
C21A C20A H20A 114.4 . . ?
C16A C20A H20A 114.4 . . ?
C20A C21A C23A 124.1(2) . . ?
C20A C21A C22A 119.3(2) . . ?
C23A C21A C22A 116.5(3) . . ?
O2A C22A N3A 123.2(2) . . ?
O2A C22A C21A 120.2(3) . . ?
N3A C22A C21A 116.6(2) . . ?
N2A C23A C21A 176.8(3) . . ?
C2B O1B C1B 117.7(3) . . ?
C19B N1B C8B 108.3(2) . . ?
C19B N1B C4B 125.1(2) . . ?
C8B N1B C4B 125.8(2) . . ?
C22B N3B H3BA 120.0 . . ?
C22B N3B H3BB 120.0 . . ?
H3BA N3B H3BB 120.0 . . ?
O1B C1B H1BA 109.5 . . ?
O1B C1B H1BB 109.5 . . ?
H1BA C1B H1BB 109.5 . . ?
O1B C1B H1BC 109.5 . . ?
H1BA C1B H1BC 109.5 . . ?
H1BB C1B H1BC 109.5 . . ?
O1B C2B C7B 124.2(3) . . ?
O1B C2B C3B 115.9(3) . . ?
C7B C2B C3B 119.9(3) . . ?
C4B C3B C2B 119.9(3) . . ?
C4B C3B H3B 120.0 . . ?
C2B C3B H3B 120.0 . . ?
C3B C4B C5B 121.0(3) . . ?
C3B C4B N1B 120.3(3) . . ?
C5B C4B N1B 118.6(3) . . ?
C6B C5B C4B 118.7(3) . . ?
C6B C5B H5B 120.7 . . ?
C4B C5B H5B 120.7 . . ?
C5B C6B C7B 120.9(3) . . ?
C5B C6B H6B 119.6 . . ?
C7B C6B H6B 119.6 . . ?
C2B C7B C6B 119.6(3) . . ?
C2B C7B H7B 120.2 . . ?
C6B C7B H7B 120.2 . . ?
C9B C8B N1B 129.7(3) . . ?
C9B C8B C13B 121.8(3) . . ?
N1B C8B C13B 108.5(2) . . ?
C10B C9B C8B 117.7(3) . . ?
C10B C9B H9B 121.1 . . ?
C8B C9B H9B 121.1 . . ?
C9B C10B C11B 121.9(3) . . ?
C9B C10B H10B 119.0 . . ?
C11B C10B H10B 119.0 . . ?
C12B C11B C10B 120.6(3) . . ?
C12B C11B H11B 119.7 . . ?
C10B C11B H11B 119.7 . . ?
C11B C12B C13B 118.6(3) . . ?
C11B C12B H12B 120.7 . . ?
C13B C12B H12B 120.7 . . ?
C12B C13B C8B 119.3(3) . . ?
C12B C13B C14B 134.0(3) . . ?
C8B C13B C14B 106.7(2) . . ?
C15B C14B C19B 119.5(3) . . ?
C15B C14B C13B 133.7(3) . . ?
C19B C14B C13B 106.8(2) . . ?
C14B C15B C16B 119.7(3) . . ?
C14B C15B H15B 120.1 . . ?
C16B C15B H15B 120.1 . . ?
C15B C16B C17B 118.8(2) . . ?
C15B C16B C20B 117.7(2) . . ?
C17B C16B C20B 123.4(3) . . ?
C18B C17B C16B 122.4(3) . . ?
C18B C17B H17B 118.8 . . ?
C16B C17B H17B 118.8 . . ?
C17B C18B C19B 117.4(3) . . ?
C17B C18B H18B 121.3 . . ?
C19B C18B H18B 121.3 . . ?
N1B C19B C18B 128.2(3) . . ?
N1B C19B C14B 109.7(3) . . ?
C18B C19B C14B 122.0(3) . . ?
C21B C20B C16B 131.3(3) . . ?
C21B C20B H20B 114.4 . . ?
C16B C20B H20B 114.4 . . ?
C20B C21B C23B 124.6(2) . . ?
C20B C21B C22B 118.8(3) . . ?
C23B C21B C22B 116.6(3) . . ?
O2B C22B N3B 123.2(2) . . ?
O2B C22B C21B 120.4(3) . . ?
N3B C22B C21B 116.3(3) . . ?
N2B C23B C21B 177.7(3) . . ?

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
C1A O1A C2A C7A -10.4(5) . . . . ?
C1A O1A C2A C3A 168.2(3) . . . . ?
O1A C2A C3A C4A -179.7(3) . . . . ?
C7A C2A C3A C4A -1.1(5) . . . . ?
C2A C3A C4A C5A 1.6(5) . . . . ?
C2A C3A C4A N1A 179.5(3) . . . . ?
C19A N1A C4A C5A 51.1(4) . . . . ?
C8A N1A C4A C5A -128.1(3) . . . . ?
C19A N1A C4A C3A -126.8(3) . . . . ?
C8A N1A C4A C3A 54.1(4) . . . . ?
C3A C4A C5A C6A 0.7(5) . . . . ?
N1A C4A C5A C6A -177.2(3) . . . . ?
C4A C5A C6A C7A -3.7(6) . . . . ?
O1A C2A C7A C6A 176.8(4) . . . . ?
C3A C2A C7A C6A -1.8(6) . . . . ?
C5A C6A C7A C2A 4.2(7) . . . . ?
C19A N1A C8A C9A -179.9(3) . . . . ?
C4A N1A C8A C9A -0.7(4) . . . . ?
C19A N1A C8A C13A -0.4(3) . . . . ?
C4A N1A C8A C13A 178.8(2) . . . . ?
N1A C8A C9A C10A -179.7(3) . . . . ?
C13A C8A C9A C10A 0.8(4) . . . . ?
C8A C9A C10A C11A -0.1(5) . . . . ?
C9A C10A C11A C12A -1.1(5) . . . . ?
C10A C11A C12A C13A 1.6(5) . . . . ?
C11A C12A C13A C8A -0.9(4) . . . . ?
C11A C12A C13A C14A 178.7(3) . . . . ?
C9A C8A C13A C12A -0.3(4) . . . . ?
N1A C8A C13A C12A -179.9(2) . . . . ?
C9A C8A C13A C14A 180.0(3) . . . . ?
N1A C8A C13A C14A 0.4(3) . . . . ?
C12A C13A C14A C15A -1.3(5) . . . . ?
C8A C13A C14A C15A 178.4(3) . . . . ?
C12A C13A C14A C19A -179.9(3) . . . . ?
C8A C13A C14A C19A -0.2(3) . . . . ?
C19A C14A C15A C16A 0.1(4) . . . . ?
C13A C14A C15A C16A -178.4(3) . . . . ?
C14A C15A C16A C17A 0.8(4) . . . . ?
C14A C15A C16A C20A 179.7(2) . . . . ?
C15A C16A C17A C18A -1.1(4) . . . . ?
C20A C16A C17A C18A -179.9(3) . . . . ?
C16A C17A C18A C19A 0.5(5) . . . . ?
C8A N1A C19A C18A -177.7(3) . . . . ?
C4A N1A C19A C18A 3.1(5) . . . . ?
C8A N1A C19A C14A 0.3(3) . . . . ?
C4A N1A C19A C14A -179.0(2) . . . . ?
C17A C18A C19A N1A 178.2(3) . . . . ?
C17A C18A C19A C14A 0.4(4) . . . . ?
C15A C14A C19A N1A -178.9(2) . . . . ?
C13A C14A C19A N1A 0.0(3) . . . . ?
C15A C14A C19A C18A -0.7(4) . . . . ?
C13A C14A C19A C18A 178.1(3) . . . . ?
C15A C16A C20A C21A 168.9(3) . . . . ?
C17A C16A C20A C21A -12.3(5) . . . . ?
C16A C20A C21A C23A -4.3(5) . . . . ?
C16A C20A C21A C22A 178.2(3) . . . . ?
C20A C21A C22A O2A 5.9(4) . . . . ?
C23A C21A C22A O2A -171.7(3) . . . . ?
C20A C21A C22A N3A -174.2(3) . . . . ?
C23A C21A C22A N3A 8.1(4) . . . . ?
C1B O1B C2B C7B -6.9(6) . . . . ?
C1B O1B C2B C3B 173.6(4) . . . . ?
O1B C2B C3B C4B -178.9(3) . . . . ?
C7B C2B C3B C4B 1.6(6) . . . . ?
C2B C3B C4B C5B -0.8(5) . . . . ?
C2B C3B C4B N1B 179.6(3) . . . . ?
C19B N1B C4B C3B -128.2(3) . . . . ?
C8B N1B C4B C3B 63.8(4) . . . . ?
C19B N1B C4B C5B 52.2(4) . . . . ?
C8B N1B C4B C5B -115.8(3) . . . . ?
C3B C4B C5B C6B 0.2(5) . . . . ?
N1B C4B C5B C6B 179.8(3) . . . . ?
C4B C5B C6B C7B -0.4(5) . . . . ?
O1B C2B C7B C6B 178.8(4) . . . . ?
C3B C2B C7B C6B -1.8(6) . . . . ?
C5B C6B C7B C2B 1.2(6) . . . . ?
C19B N1B C8B C9B 178.9(3) . . . . ?
C4B N1B C8B C9B -11.4(5) . . . . ?
C19B N1B C8B C13B 0.0(3) . . . . ?
C4B N1B C8B C13B 169.7(3) . . . . ?
N1B C8B C9B C10B -178.9(3) . . . . ?
C13B C8B C9B C10B -0.1(4) . . . . ?
C8B C9B C10B C11B 1.0(5) . . . . ?
C9B C10B C11B C12B -1.3(5) . . . . ?
C10B C11B C12B C13B 0.7(5) . . . . ?
C11B C12B C13B C8B 0.1(4) . . . . ?
C11B C12B C13B C14B 178.5(3) . . . . ?
C9B C8B C13B C12B -0.4(4) . . . . ?
N1B C8B C13B C12B 178.6(2) . . . . ?
C9B C8B C13B C14B -179.2(3) . . . . ?
N1B C8B C13B C14B -0.2(3) . . . . ?
C12B C13B C14B C15B 2.1(5) . . . . ?
C8B C13B C14B C15B -179.4(3) . . . . ?
C12B C13B C14B C19B -178.2(3) . . . . ?
C8B C13B C14B C19B 0.3(3) . . . . ?
C19B C14B C15B C16B 2.0(4) . . . . ?
C13B C14B C15B C16B -178.3(3) . . . . ?
C14B C15B C16B C17B 1.5(4) . . . . ?
C14B C15B C16B C20B 179.5(2) . . . . ?
C15B C16B C17B C18B -3.0(4) . . . . ?
C20B C16B C17B C18B 179.1(3) . . . . ?
C16B C17B C18B C19B 0.9(5) . . . . ?
C8B N1B C19B C18B -175.8(3) . . . . ?
C4B N1B C19B C18B 14.4(5) . . . . ?
C8B N1B C19B C14B 0.2(3) . . . . ?
C4B N1B C19B C14B -169.6(3) . . . . ?
C17B C18B C19B N1B 178.3(3) . . . . ?
C17B C18B C19B C14B 2.8(5) . . . . ?
C15B C14B C19B N1B 179.5(2) . . . . ?
C13B C14B C19B N1B -0.3(3) . . . . ?
C15B C14B C19B C18B -4.2(4) . . . . ?
C13B C14B C19B C18B 176.0(3) . . . . ?
C15B C16B C20B C21B 173.1(3) . . . . ?
C17B C16B C20B C21B -9.0(5) . . . . ?
C16B C20B C21B C23B -1.2(5) . . . . ?
C16B C20B C21B C22B 179.2(3) . . . . ?
C20B C21B C22B O2B 4.1(4) . . . . ?
C23B C21B C22B O2B -175.5(3) . . . . ?
C20B C21B C22B N3B -177.6(3) . . . . ?
C23B C21B C22B N3B 2.8(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N3A H3AA O2B 0.87 1.98 2.850(3) 178.6 . yes
N3A H3AB O1B 0.87 2.46 3.049(3) 126.0 2_766 yes
C3A H3A O2A 0.94 2.30 3.240(4) 178.2 2_567 yes
N3B H3BA O2A 0.87 1.98 2.845(3) 176.6 . yes
N3B H3BB O1A 0.87 2.28 2.933(4) 132.4 2_567 yes
C3B H3B O2B 0.94 2.41 3.338(4) 170.9 2_766 yes

_refine_diff_density_max         0.309
_refine_diff_density_min         -0.326
_refine_diff_density_rms         0.068
























