# Supplementary Information (SI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# 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_hqw026
_database_code_depnum_ccdc_archive 'CCDC 2467819'
loop_
_audit_author_name
_audit_author_address
'Yuqiao Zhou'
;College of Chemistry, Sichuan University, Chengdu, China
China
;
_audit_update_record             
;
2025-06-27 deposited with the CCDC.	2025-09-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/1
_shelx_SHELXL_version_number     2019/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C32 H23 N3 O2'
_chemical_formula_sum            'C32 H23 N3 O2'
_chemical_formula_weight         481.53

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_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, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   9.7807(2)
_cell_length_b                   12.8377(2)
_cell_length_c                   20.0417(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2516.47(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    9904
_cell_measurement_theta_min      4.09
_cell_measurement_theta_max      79.39

_exptl_crystal_description       rod
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.271
_exptl_crystal_F_000             1008
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.440
_exptl_crystal_size_mid          0.154
_exptl_crystal_size_min          0.135
_exptl_absorpt_coefficient_mu    0.639
_shelx_estimated_absorpt_T_min   0.766
_shelx_estimated_absorpt_T_max   0.919
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.8334
_exptl_absorpt_correction_T_max  0.9971
_exptl_absorpt_process_details   'SADABS (Krause et al., 2015)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 Venture Photon II'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15801
_diffrn_reflns_av_unetI/netI     0.0341
_diffrn_reflns_av_R_equivalents  0.0357
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         4.089
_diffrn_reflns_theta_max         79.749
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.960
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.960
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.950
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             5225
_reflns_number_gt                4990
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.750
_reflns_Friedel_fraction_max     0.936
_reflns_Friedel_fraction_full    0.991

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

_computing_data_collection       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0475P)²+0.2355P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
; 
 Flack x determined using 2069 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   -0.10(9)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         5225
_refine_ls_number_parameters     335
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0361
_refine_ls_R_factor_gt           0.0337
_refine_ls_wR_factor_ref         0.0855
_refine_ls_wR_factor_gt          0.0835
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.035
_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 0.39049(18) 0.33992(13) 0.79659(7) 0.0447(4) Uani 1 1 d . . . . .
O2 O 0.57462(16) 0.49326(13) 0.68749(8) 0.0463(4) Uani 1 1 d . . . . .
N1 N 0.17426(15) 0.40804(10) 0.70652(6) 0.0240(3) Uani 1 1 d . . . . .
N2 N 0.11939(14) 0.47350(10) 0.66060(6) 0.0238(3) Uani 1 1 d . . . . .
N3 N 0.44792(17) 0.19504(12) 0.65230(8) 0.0349(3) Uani 1 1 d . . . . .
C1 C 0.5254(2) 0.11685(16) 0.63006(11) 0.0443(5) Uani 1 1 d . . . . .
H1 H 0.500589 0.084437 0.589204 0.053 Uiso 1 1 calc R U . . .
C2 C 0.6403(2) 0.08023(16) 0.66328(13) 0.0471(5) Uani 1 1 d . . . . .
H2 H 0.692274 0.024157 0.645604 0.057 Uiso 1 1 calc R U . . .
C3 C 0.6771(2) 0.12693(18) 0.72235(12) 0.0470(5) Uani 1 1 d . . . . .
H3 H 0.755552 0.103845 0.746078 0.056 Uiso 1 1 calc R U . . .
C4 C 0.5985(2) 0.20788(16) 0.74676(10) 0.0394(4) Uani 1 1 d . . . . .
H4 H 0.621343 0.241499 0.787487 0.047 Uiso 1 1 calc R U . . .
C5 C 0.48535(18) 0.23856(13) 0.71000(8) 0.0290(3) Uani 1 1 d . . . . .
C6 C 0.39294(19) 0.32096(13) 0.73748(8) 0.0292(3) Uani 1 1 d . . . . .
C7 C 0.30332(18) 0.37864(12) 0.69010(8) 0.0256(3) Uani 1 1 d . . . . .
C8 C 0.33621(17) 0.42788(12) 0.63078(8) 0.0250(3) Uani 1 1 d . . . . .
C9 C 0.21813(16) 0.48705(12) 0.61510(8) 0.0239(3) Uani 1 1 d . . . . .
C11 C 0.09083(17) 0.37220(12) 0.76071(7) 0.0241(3) Uani 1 1 d . . . . .
C12 C 0.01857(19) 0.44351(13) 0.79860(9) 0.0302(3) Uani 1 1 d . . . . .
H12 H 0.024419 0.515917 0.789233 0.036 Uiso 1 1 calc R U . . .
C13 C -0.0629(2) 0.40741(16) 0.85069(9) 0.0380(4) Uani 1 1 d . . . . .
H13 H -0.112879 0.455506 0.877194 0.046 Uiso 1 1 calc R U . . .
C14 C -0.0714(2) 0.30147(17) 0.86411(9) 0.0377(4) Uani 1 1 d . . . . .
H14 H -0.127382 0.277320 0.899620 0.045 Uiso 1 1 calc R U . . .
C15 C 0.0014(2) 0.23124(14) 0.82596(9) 0.0364(4) Uani 1 1 d . . . . .
H15 H -0.004196 0.158818 0.835315 0.044 Uiso 1 1 calc R U . . .
C16 C 0.0829(2) 0.26658(13) 0.77380(8) 0.0306(3) Uani 1 1 d . . . . .
H16 H 0.132769 0.218437 0.747291 0.037 Uiso 1 1 calc R U . . .
C21 C 0.46668(18) 0.42381(13) 0.59358(8) 0.0274(3) Uani 1 1 d . . . . .
C22 C 0.5852(2) 0.46006(15) 0.62292(10) 0.0356(4) Uani 1 1 d . . . . .
C23 C 0.7096(2) 0.46341(19) 0.58702(14) 0.0499(5) Uani 1 1 d . . . . .
H23 H 0.789599 0.491290 0.607082 0.060 Uiso 1 1 calc R U . . .
C24 C 0.7135(2) 0.4261(2) 0.52315(13) 0.0508(5) Uani 1 1 d . . . . .
H24 H 0.796929 0.429695 0.498950 0.061 Uiso 1 1 calc R U . . .
C25 C 0.5982(2) 0.38278(15) 0.49233(10) 0.0370(4) Uani 1 1 d . . . . .
C26 C 0.6051(3) 0.33569(18) 0.42800(10) 0.0460(5) Uani 1 1 d . . . . .
H26 H 0.689382 0.334734 0.404429 0.055 Uiso 1 1 calc R U . . .
C27 C 0.4920(3) 0.29215(18) 0.40012(10) 0.0493(6) Uani 1 1 d . . . . .
H27 H 0.498020 0.260159 0.357479 0.059 Uiso 1 1 calc R U . . .
C28 C 0.3662(3) 0.29420(17) 0.43408(9) 0.0431(5) Uani 1 1 d . . . . .
H28 H 0.287375 0.264854 0.413768 0.052 Uiso 1 1 calc R U . . .
C29 C 0.3563(2) 0.33827(15) 0.49639(9) 0.0346(4) Uani 1 1 d . . . . .
H29 H 0.270721 0.338788 0.518783 0.041 Uiso 1 1 calc R U . . .
C30 C 0.47167(19) 0.38271(13) 0.52745(8) 0.0292(3) Uani 1 1 d . . . . .
C31 C 0.6957(3) 0.5076(3) 0.72436(16) 0.0743(10) Uani 1 1 d . . . . .
H31A H 0.673229 0.515343 0.771749 0.111 Uiso 1 1 calc R U . . .
H31B H 0.742764 0.570312 0.708624 0.111 Uiso 1 1 calc R U . . .
H31C H 0.755389 0.446959 0.718367 0.111 Uiso 1 1 calc R U . . .
C41 C 0.19510(18) 0.55712(12) 0.55783(8) 0.0262(3) Uani 1 1 d . . . . .
C42 C 0.2999(2) 0.62022(15) 0.53327(10) 0.0383(4) Uani 1 1 d . . . . .
H42 H 0.388003 0.618117 0.553196 0.046 Uiso 1 1 calc R U . . .
C43 C 0.2750(3) 0.68629(17) 0.47945(11) 0.0492(6) Uani 1 1 d . . . . .
H43 H 0.346641 0.728897 0.462697 0.059 Uiso 1 1 calc R U . . .
C44 C 0.1478(3) 0.69042(17) 0.45034(9) 0.0523(6) Uani 1 1 d . . . . .
H44 H 0.131383 0.736181 0.413960 0.063 Uiso 1 1 calc R U . . .
C45 C 0.0437(3) 0.62767(17) 0.47426(10) 0.0490(5) Uani 1 1 d . . . . .
H45 H -0.044018 0.629825 0.453983 0.059 Uiso 1 1 calc R U . . .
C46 C 0.0674(2) 0.56144(14) 0.52795(9) 0.0355(4) Uani 1 1 d . . . . .
H46 H -0.004525 0.518775 0.544286 0.043 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 C6 1.210(2) . ?
O2 C22 1.366(2) . ?
O2 C31 1.408(3) . ?
N1 N2 1.3570(19) . ?
N1 C7 1.358(2) . ?
N1 C11 1.4342(19) . ?
N2 C9 1.340(2) . ?
N3 C1 1.334(3) . ?
N3 C5 1.335(2) . ?
C1 C2 1.388(3) . ?
C2 C3 1.375(4) . ?
C3 C4 1.382(3) . ?
C4 C5 1.387(3) . ?
C5 C6 1.496(2) . ?
C6 C7 1.490(2) . ?
C7 C8 1.384(2) . ?
C8 C9 1.418(2) . ?
C8 C21 1.479(2) . ?
C9 C41 1.476(2) . ?
C11 C16 1.383(2) . ?
C11 C12 1.384(2) . ?
C12 C13 1.393(2) . ?
C13 C14 1.389(3) . ?
C14 C15 1.380(3) . ?
C15 C16 1.391(3) . ?
C21 C22 1.381(3) . ?
C21 C30 1.427(2) . ?
C22 C23 1.414(3) . ?
C23 C24 1.367(4) . ?
C24 C25 1.401(3) . ?
C25 C30 1.424(3) . ?
C25 C26 1.426(3) . ?
C26 C27 1.359(4) . ?
C27 C28 1.406(3) . ?
C28 C29 1.374(3) . ?
C29 C30 1.409(3) . ?
C41 C46 1.386(3) . ?
C41 C42 1.396(3) . ?
C42 C43 1.394(3) . ?
C43 C44 1.376(4) . ?
C44 C45 1.383(4) . ?
C45 C46 1.391(3) . ?

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
C22 O2 C31 118.29(18) . . ?
N2 N1 C7 112.04(13) . . ?
N2 N1 C11 119.16(13) . . ?
C7 N1 C11 128.55(14) . . ?
C9 N2 N1 104.89(13) . . ?
C1 N3 C5 116.63(17) . . ?
N3 C1 C2 123.7(2) . . ?
C3 C2 C1 118.53(19) . . ?
C2 C3 C4 119.1(2) . . ?
C3 C4 C5 118.0(2) . . ?
N3 C5 C4 124.06(17) . . ?
N3 C5 C6 116.67(15) . . ?
C4 C5 C6 119.17(16) . . ?
O1 C6 C7 120.84(16) . . ?
O1 C6 C5 120.98(16) . . ?
C7 C6 C5 118.18(14) . . ?
N1 C7 C8 107.30(14) . . ?
N1 C7 C6 122.05(14) . . ?
C8 C7 C6 129.63(16) . . ?
C7 C8 C9 104.23(14) . . ?
C7 C8 C21 128.13(15) . . ?
C9 C8 C21 127.59(14) . . ?
N2 C9 C8 111.52(14) . . ?
N2 C9 C41 119.91(14) . . ?
C8 C9 C41 128.58(15) . . ?
C16 C11 C12 121.04(15) . . ?
C16 C11 N1 119.35(14) . . ?
C12 C11 N1 119.60(14) . . ?
C11 C12 C13 118.91(16) . . ?
C14 C13 C12 120.35(18) . . ?
C15 C14 C13 120.11(17) . . ?
C14 C15 C16 119.93(16) . . ?
C11 C16 C15 119.65(16) . . ?
C22 C21 C30 119.43(16) . . ?
C22 C21 C8 119.86(15) . . ?
C30 C21 C8 120.71(16) . . ?
O2 C22 C21 116.41(17) . . ?
O2 C22 C23 122.53(19) . . ?
C21 C22 C23 121.05(18) . . ?
C24 C23 C22 119.4(2) . . ?
C23 C24 C25 121.93(19) . . ?
C24 C25 C30 118.82(17) . . ?
C24 C25 C26 121.9(2) . . ?
C30 C25 C26 119.2(2) . . ?
C27 C26 C25 120.5(2) . . ?
C26 C27 C28 120.35(18) . . ?
C29 C28 C27 120.6(2) . . ?
C28 C29 C30 120.8(2) . . ?
C29 C30 C25 118.54(16) . . ?
C29 C30 C21 122.17(16) . . ?
C25 C30 C21 119.24(17) . . ?
C46 C41 C42 119.07(16) . . ?
C46 C41 C9 119.87(16) . . ?
C42 C41 C9 121.06(17) . . ?
C43 C42 C41 119.9(2) . . ?
C44 C43 C42 120.6(2) . . ?
C43 C44 C45 119.74(18) . . ?
C44 C45 C46 120.1(2) . . ?
C41 C46 C45 120.6(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C7 N1 N2 C9 -1.36(17) . . . . ?
C11 N1 N2 C9 -176.19(13) . . . . ?
C5 N3 C1 C2 -0.3(3) . . . . ?
N3 C1 C2 C3 -0.2(4) . . . . ?
C1 C2 C3 C4 0.4(3) . . . . ?
C2 C3 C4 C5 -0.2(3) . . . . ?
C1 N3 C5 C4 0.5(3) . . . . ?
C1 N3 C5 C6 -175.69(17) . . . . ?
C3 C4 C5 N3 -0.3(3) . . . . ?
C3 C4 C5 C6 175.82(18) . . . . ?
N3 C5 C6 O1 155.25(19) . . . . ?
C4 C5 C6 O1 -21.2(3) . . . . ?
N3 C5 C6 C7 -24.4(2) . . . . ?
C4 C5 C6 C7 159.19(17) . . . . ?
N2 N1 C7 C8 0.67(18) . . . . ?
C11 N1 C7 C8 174.89(14) . . . . ?
N2 N1 C7 C6 170.10(14) . . . . ?
C11 N1 C7 C6 -15.7(2) . . . . ?
O1 C6 C7 N1 -36.7(3) . . . . ?
C5 C6 C7 N1 142.98(16) . . . . ?
O1 C6 C7 C8 130.2(2) . . . . ?
C5 C6 C7 C8 -50.2(2) . . . . ?
N1 C7 C8 C9 0.28(17) . . . . ?
C6 C7 C8 C9 -168.07(16) . . . . ?
N1 C7 C8 C21 177.81(15) . . . . ?
C6 C7 C8 C21 9.5(3) . . . . ?
N1 N2 C9 C8 1.54(17) . . . . ?
N1 N2 C9 C41 -178.35(13) . . . . ?
C7 C8 C9 N2 -1.16(18) . . . . ?
C21 C8 C9 N2 -178.71(15) . . . . ?
C7 C8 C9 C41 178.72(15) . . . . ?
C21 C8 C9 C41 1.2(3) . . . . ?
N2 N1 C11 C16 128.57(17) . . . . ?
C7 N1 C11 C16 -45.3(2) . . . . ?
N2 N1 C11 C12 -50.8(2) . . . . ?
C7 N1 C11 C12 135.37(18) . . . . ?
C16 C11 C12 C13 0.2(3) . . . . ?
N1 C11 C12 C13 179.47(17) . . . . ?
C11 C12 C13 C14 -0.2(3) . . . . ?
C12 C13 C14 C15 0.2(3) . . . . ?
C13 C14 C15 C16 -0.3(3) . . . . ?
C12 C11 C16 C15 -0.2(3) . . . . ?
N1 C11 C16 C15 -179.54(16) . . . . ?
C14 C15 C16 C11 0.3(3) . . . . ?
C7 C8 C21 C22 -61.6(2) . . . . ?
C9 C8 C21 C22 115.3(2) . . . . ?
C7 C8 C21 C30 118.36(19) . . . . ?
C9 C8 C21 C30 -64.7(2) . . . . ?
C31 O2 C22 C21 165.3(2) . . . . ?
C31 O2 C22 C23 -15.5(3) . . . . ?
C30 C21 C22 O2 -176.67(16) . . . . ?
C8 C21 C22 O2 3.3(3) . . . . ?
C30 C21 C22 C23 4.2(3) . . . . ?
C8 C21 C22 C23 -175.85(18) . . . . ?
O2 C22 C23 C24 178.2(2) . . . . ?
C21 C22 C23 C24 -2.7(4) . . . . ?
C22 C23 C24 C25 -1.1(4) . . . . ?
C23 C24 C25 C30 3.4(3) . . . . ?
C23 C24 C25 C26 -174.4(2) . . . . ?
C24 C25 C26 C27 178.4(2) . . . . ?
C30 C25 C26 C27 0.7(3) . . . . ?
C25 C26 C27 C28 0.8(3) . . . . ?
C26 C27 C28 C29 -1.3(3) . . . . ?
C27 C28 C29 C30 0.3(3) . . . . ?
C28 C29 C30 C25 1.2(3) . . . . ?
C28 C29 C30 C21 -176.39(17) . . . . ?
C24 C25 C30 C29 -179.51(18) . . . . ?
C26 C25 C30 C29 -1.7(3) . . . . ?
C24 C25 C30 C21 -1.8(3) . . . . ?
C26 C25 C30 C21 176.00(17) . . . . ?
C22 C21 C30 C29 175.74(17) . . . . ?
C8 C21 C30 C29 -4.3(2) . . . . ?
C22 C21 C30 C25 -1.8(2) . . . . ?
C8 C21 C30 C25 178.16(15) . . . . ?
N2 C9 C41 C46 -37.2(2) . . . . ?
C8 C9 C41 C46 142.90(17) . . . . ?
N2 C9 C41 C42 142.29(17) . . . . ?
C8 C9 C41 C42 -37.6(2) . . . . ?
C46 C41 C42 C43 0.0(3) . . . . ?
C9 C41 C42 C43 -179.49(17) . . . . ?
C41 C42 C43 C44 0.3(3) . . . . ?
C42 C43 C44 C45 -0.6(3) . . . . ?
C43 C44 C45 C46 0.6(3) . . . . ?
C42 C41 C46 C45 0.0(3) . . . . ?
C9 C41 C46 C45 179.49(17) . . . . ?
C44 C45 C46 C41 -0.3(3) . . . . ?

_refine_diff_density_max         0.139
_refine_diff_density_min         -0.194
_refine_diff_density_rms         0.037


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: DCM, Hexane'
####################################################################### 
# 
# 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_hqw031
_database_code_depnum_ccdc_archive 'CCDC 2467822'
loop_
_audit_author_name
_audit_author_address
'Yuqiao Zhou'
;College of Chemistry, Sichuan University, Chengdu, China
China
;
_audit_update_record             
;
2025-06-27 deposited with the CCDC.	2025-09-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/1
_shelx_SHELXL_version_number     2019/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H16 N2 O3 S'
_chemical_formula_sum            'C22 H16 N2 O3 S'
_chemical_formula_weight         388.43

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 '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/c'
_space_group_name_Hall           '-P 2ybc'

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

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

_cell_length_a                   11.3478(2)
_cell_length_b                   11.1173(2)
_cell_length_c                   14.7905(3)
_cell_angle_alpha                90
_cell_angle_beta                 100.9880(10)
_cell_angle_gamma                90
_cell_volume                     1831.72(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    9684
_cell_measurement_theta_min      2.31
_cell_measurement_theta_max      27.38

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.409
_exptl_crystal_F_000             808
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.767
_exptl_crystal_size_mid          0.441
_exptl_crystal_size_min          0.279
_exptl_absorpt_coefficient_mu    0.203
_shelx_estimated_absorpt_T_min   0.860
_shelx_estimated_absorpt_T_max   0.945
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.9320
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'SADABS (Krause et al., 2015)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 Venture Photon II'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18620
_diffrn_reflns_av_unetI/netI     0.0274
_diffrn_reflns_av_R_equivalents  0.0350
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.588
_diffrn_reflns_theta_max         27.493
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4194
_reflns_number_gt                3541
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX5'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0409P)²+0.6572P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2019/1 (Sheldrick 2019)'
_refine_ls_extinction_coef       0.0165(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4194
_refine_ls_number_parameters     254
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0466
_refine_ls_R_factor_gt           0.0370
_refine_ls_wR_factor_ref         0.0958
_refine_ls_wR_factor_gt          0.0887
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.039
_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
S S 0.91752(3) 0.46793(3) 0.76485(3) 0.03094(12) Uani 1 1 d . . . . .
O1 O 0.55781(12) 0.24453(11) 0.61135(10) 0.0551(4) Uani 1 1 d . . . . .
O2 O 1.02811(9) 0.51949(11) 0.81231(8) 0.0419(3) Uani 1 1 d . . . . .
O3 O 0.91587(10) 0.40323(10) 0.68055(7) 0.0393(3) Uani 1 1 d . . . . .
N1 N 0.69694(10) 0.57977(11) 0.69824(8) 0.0272(3) Uani 1 1 d . . . . .
N2 N 0.29096(11) 0.41239(12) 0.54533(9) 0.0362(3) Uani 1 1 d . . . . .
C1 C 0.64193(13) 0.47294(13) 0.66601(10) 0.0294(3) Uani 1 1 d . . . . .
H1 H 0.692476 0.404112 0.673097 0.035 Uiso 1 1 calc R U . . .
C2 C 0.52874(13) 0.45323(13) 0.62667(10) 0.0323(3) Uani 1 1 d . . . . .
H2 H 0.473291 0.518061 0.615884 0.039 Uiso 1 1 calc R U . . .
C3 C 0.48974(14) 0.33068(14) 0.59993(10) 0.0333(3) Uani 1 1 d . . . . .
C4 C 0.36029(13) 0.31396(13) 0.55504(10) 0.0308(3) Uani 1 1 d . . . . .
C5 C 0.31916(15) 0.20140(15) 0.52295(11) 0.0377(4) Uani 1 1 d . . . . .
H5 H 0.370430 0.133166 0.532396 0.045 Uiso 1 1 calc R U . . .
C6 C 0.20130(16) 0.19115(17) 0.47677(11) 0.0431(4) Uani 1 1 d . . . . .
H6 H 0.171061 0.116011 0.451915 0.052 Uiso 1 1 calc R U . . .
C7 C 0.12899(16) 0.29075(18) 0.46742(12) 0.0469(4) Uani 1 1 d . . . . .
H7 H 0.047432 0.285590 0.437122 0.056 Uiso 1 1 calc R U . . .
C8 C 0.17694(15) 0.39873(17) 0.50289(12) 0.0445(4) Uani 1 1 d . . . . .
H8 H 0.125939 0.467201 0.496762 0.053 Uiso 1 1 calc R U . . .
C11 C 0.81704(12) 0.58880(13) 0.74468(10) 0.0282(3) Uani 1 1 d . . . . .
C12 C 0.84609(13) 0.70428(13) 0.76738(10) 0.0304(3) Uani 1 1 d . . . . .
H12 H 0.921172 0.732643 0.800118 0.036 Uiso 1 1 calc R U . . .
C13 C 0.74265(13) 0.77557(13) 0.73289(10) 0.0290(3) Uani 1 1 d . . . . .
C14 C 0.65046(12) 0.69717(13) 0.69157(10) 0.0277(3) Uani 1 1 d . . . . .
C15 C 0.53803(13) 0.74120(14) 0.65036(12) 0.0363(3) Uani 1 1 d . . . . .
H15 H 0.475131 0.688499 0.623511 0.044 Uiso 1 1 calc R U . . .
C16 C 0.52145(15) 0.86422(15) 0.65000(13) 0.0424(4) Uani 1 1 d . . . . .
H16 H 0.445278 0.896111 0.622760 0.051 Uiso 1 1 calc R U . . .
C17 C 0.61282(16) 0.94316(15) 0.68830(12) 0.0415(4) Uani 1 1 d . . . . .
H17 H 0.598680 1.027422 0.685389 0.050 Uiso 1 1 calc R U . . .
C18 C 0.72338(15) 0.89996(14) 0.73031(11) 0.0360(3) Uani 1 1 d . . . . .
H18 H 0.785479 0.953587 0.757071 0.043 Uiso 1 1 calc R U . . .
C21 C 0.86176(12) 0.37190(13) 0.84176(10) 0.0289(3) Uani 1 1 d . . . . .
C22 C 0.86466(15) 0.41235(15) 0.93094(11) 0.0385(4) Uani 1 1 d . . . . .
H22 H 0.894907 0.490157 0.949023 0.046 Uiso 1 1 calc R U . . .
C23 C 0.82318(16) 0.33850(17) 0.99316(12) 0.0457(4) Uani 1 1 d . . . . .
H23 H 0.824195 0.365596 1.054220 0.055 Uiso 1 1 calc R U . . .
C24 C 0.78012(15) 0.22494(16) 0.96636(12) 0.0407(4) Uani 1 1 d . . . . .
H24 H 0.751689 0.174122 1.009193 0.049 Uiso 1 1 calc R U . . .
C25 C 0.77831(14) 0.18514(15) 0.87759(12) 0.0382(4) Uani 1 1 d . . . . .
H25 H 0.748849 0.106970 0.859837 0.046 Uiso 1 1 calc R U . . .
C26 C 0.81912(13) 0.25838(14) 0.81432(11) 0.0339(3) Uani 1 1 d . . . . .
H26 H 0.817883 0.231228 0.753243 0.041 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
S O2 1.4355(11) . ?
S O3 1.4365(11) . ?
S C11 1.7507(14) . ?
S C21 1.7631(15) . ?
O1 C3 1.2218(19) . ?
N1 C1 1.3835(18) . ?
N1 C14 1.4041(18) . ?
N1 C11 1.4079(17) . ?
N2 C8 1.3348(19) . ?
N2 C4 1.339(2) . ?
C1 C2 1.324(2) . ?
C2 C3 1.463(2) . ?
C3 C4 1.504(2) . ?
C4 C5 1.387(2) . ?
C5 C6 1.386(2) . ?
C6 C7 1.369(3) . ?
C7 C8 1.380(2) . ?
C11 C12 1.352(2) . ?
C12 C13 1.428(2) . ?
C13 C18 1.399(2) . ?
C13 C14 1.408(2) . ?
C14 C15 1.394(2) . ?
C15 C16 1.380(2) . ?
C16 C17 1.394(2) . ?
C17 C18 1.376(2) . ?
C21 C26 1.384(2) . ?
C21 C22 1.388(2) . ?
C22 C23 1.381(2) . ?
C23 C24 1.384(2) . ?
C24 C25 1.382(2) . ?
C25 C26 1.385(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 S O3 119.34(7) . . ?
O2 S C11 104.90(7) . . ?
O3 S C11 109.64(7) . . ?
O2 S C21 108.31(7) . . ?
O3 S C21 108.06(7) . . ?
C11 S C21 105.82(7) . . ?
C1 N1 C14 129.42(12) . . ?
C1 N1 C11 124.09(12) . . ?
C14 N1 C11 106.49(11) . . ?
C8 N2 C4 117.03(14) . . ?
C2 C1 N1 129.05(14) . . ?
C1 C2 C3 119.41(14) . . ?
O1 C3 C2 122.81(14) . . ?
O1 C3 C4 120.18(14) . . ?
C2 C3 C4 117.00(13) . . ?
N2 C4 C5 123.22(14) . . ?
N2 C4 C3 116.79(13) . . ?
C5 C4 C3 119.95(14) . . ?
C6 C5 C4 118.23(16) . . ?
C7 C6 C5 119.13(15) . . ?
C6 C7 C8 118.68(16) . . ?
N2 C8 C7 123.67(17) . . ?
C12 C11 N1 110.88(12) . . ?
C12 C11 S 124.51(11) . . ?
N1 C11 S 124.53(11) . . ?
C11 C12 C13 107.06(12) . . ?
C18 C13 C14 120.02(14) . . ?
C18 C13 C12 132.21(14) . . ?
C14 C13 C12 107.68(13) . . ?
C15 C14 N1 131.11(14) . . ?
C15 C14 C13 120.98(14) . . ?
N1 C14 C13 107.86(12) . . ?
C16 C15 C14 117.54(15) . . ?
C15 C16 C17 122.14(15) . . ?
C18 C17 C16 120.49(15) . . ?
C17 C18 C13 118.79(15) . . ?
C26 C21 C22 121.17(14) . . ?
C26 C21 S 120.74(12) . . ?
C22 C21 S 118.07(12) . . ?
C23 C22 C21 119.42(15) . . ?
C22 C23 C24 119.86(15) . . ?
C25 C24 C23 120.30(16) . . ?
C24 C25 C26 120.49(15) . . ?
C21 C26 C25 118.75(14) . . ?

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
C14 N1 C1 C2 -5.6(3) . . . . ?
C11 N1 C1 C2 175.60(15) . . . . ?
N1 C1 C2 C3 -178.45(14) . . . . ?
C1 C2 C3 O1 -0.8(2) . . . . ?
C1 C2 C3 C4 -179.65(14) . . . . ?
C8 N2 C4 C5 0.4(2) . . . . ?
C8 N2 C4 C3 177.93(14) . . . . ?
O1 C3 C4 N2 179.62(15) . . . . ?
C2 C3 C4 N2 -1.5(2) . . . . ?
O1 C3 C4 C5 -2.7(2) . . . . ?
C2 C3 C4 C5 176.10(14) . . . . ?
N2 C4 C5 C6 1.5(2) . . . . ?
C3 C4 C5 C6 -175.94(13) . . . . ?
C4 C5 C6 C7 -2.3(2) . . . . ?
C5 C6 C7 C8 1.3(2) . . . . ?
C4 N2 C8 C7 -1.5(3) . . . . ?
C6 C7 C8 N2 0.7(3) . . . . ?
C1 N1 C11 C12 179.60(13) . . . . ?
C14 N1 C11 C12 0.56(16) . . . . ?
C1 N1 C11 S 2.8(2) . . . . ?
C14 N1 C11 S -176.28(10) . . . . ?
O2 S C11 C12 2.67(15) . . . . ?
O3 S C11 C12 -126.62(13) . . . . ?
C21 S C11 C12 117.08(13) . . . . ?
O2 S C11 N1 179.09(12) . . . . ?
O3 S C11 N1 49.80(14) . . . . ?
C21 S C11 N1 -66.51(13) . . . . ?
N1 C11 C12 C13 -1.47(16) . . . . ?
S C11 C12 C13 175.36(10) . . . . ?
C11 C12 C13 C18 -174.75(16) . . . . ?
C11 C12 C13 C14 1.82(16) . . . . ?
C1 N1 C14 C15 -1.0(3) . . . . ?
C11 N1 C14 C15 177.97(15) . . . . ?
C1 N1 C14 C13 -178.36(13) . . . . ?
C11 N1 C14 C13 0.61(15) . . . . ?
C18 C13 C14 C15 -2.1(2) . . . . ?
C12 C13 C14 C15 -179.18(13) . . . . ?
C18 C13 C14 N1 175.57(13) . . . . ?
C12 C13 C14 N1 -1.49(15) . . . . ?
N1 C14 C15 C16 -175.81(15) . . . . ?
C13 C14 C15 C16 1.3(2) . . . . ?
C14 C15 C16 C17 0.6(3) . . . . ?
C15 C16 C17 C18 -1.6(3) . . . . ?
C16 C17 C18 C13 0.7(2) . . . . ?
C14 C13 C18 C17 1.1(2) . . . . ?
C12 C13 C18 C17 177.30(15) . . . . ?
O2 S C21 C26 -134.40(12) . . . . ?
O3 S C21 C26 -3.81(14) . . . . ?
C11 S C21 C26 113.56(12) . . . . ?
O2 S C21 C22 44.06(13) . . . . ?
O3 S C21 C22 174.65(11) . . . . ?
C11 S C21 C22 -67.98(13) . . . . ?
C26 C21 C22 C23 -0.6(2) . . . . ?
S C21 C22 C23 -179.09(13) . . . . ?
C21 C22 C23 C24 0.5(3) . . . . ?
C22 C23 C24 C25 -0.1(3) . . . . ?
C23 C24 C25 C26 -0.2(2) . . . . ?
C22 C21 C26 C25 0.4(2) . . . . ?
S C21 C26 C25 178.77(11) . . . . ?
C24 C25 C26 C21 0.1(2) . . . . ?

_refine_diff_density_max         0.288
_refine_diff_density_min         -0.312
_refine_diff_density_rms         0.040


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: DCM, EtOAc'
####################################################################### 
# 
# 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_hqw030
_database_code_depnum_ccdc_archive 'CCDC 2467821'
loop_
_audit_author_name
_audit_author_address
'Yuqiao Zhou'
;College of Chemistry, Sichuan University, Chengdu, China
China
;
_audit_update_record             
;
2025-06-27 deposited with the CCDC.	2025-09-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/1
_shelx_SHELXL_version_number     2019/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C32 H24 N4 O3'
_chemical_formula_sum            'C32 H24 N4 O3'
_chemical_formula_weight         512.55

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_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, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   10.3004(6)
_cell_length_b                   12.8214(7)
_cell_length_c                   20.1111(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2656.0(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    9890
_cell_measurement_theta_min      4.09
_cell_measurement_theta_max      68.29

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.282
_exptl_crystal_F_000             1072
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.368
_exptl_crystal_size_mid          0.329
_exptl_crystal_size_min          0.176
_exptl_absorpt_coefficient_mu    0.677
_shelx_estimated_absorpt_T_min   0.789
_shelx_estimated_absorpt_T_max   0.890
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.7759
_exptl_absorpt_correction_T_max  0.9366
_exptl_absorpt_process_details   'SADABS (Krause et al., 2015)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 Venture Photon II'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16456
_diffrn_reflns_av_unetI/netI     0.0307
_diffrn_reflns_av_R_equivalents  0.0362
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         4.089
_diffrn_reflns_theta_max         68.282
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             4857
_reflns_number_gt                4753
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.757
_reflns_Friedel_fraction_max     0.992
_reflns_Friedel_fraction_full    0.993

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

_computing_data_collection       'Bruker APEX5'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0321P)²+0.2853P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2019/1 (Sheldrick 2019)'
_refine_ls_extinction_coef       0.0031(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
; 
 Flack x determined using 2012 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.02(6)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         4857
_refine_ls_number_parameters     354
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0280
_refine_ls_R_factor_gt           0.0272
_refine_ls_wR_factor_ref         0.0674
_refine_ls_wR_factor_gt          0.0667
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.056
_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 0.32216(13) 0.48562(14) 0.37049(8) 0.0497(4) Uani 1 1 d . . . . .
O2 O 0.52182(13) 0.42968(11) 0.34173(7) 0.0377(3) Uani 1 1 d . . . . .
O3 O 0.62351(13) 0.63909(10) 0.23366(6) 0.0354(3) Uani 1 1 d . . . . .
N1 N 0.62410(13) 0.57301(10) 0.44137(6) 0.0235(3) Uani 1 1 d . . . . .
N2 N 0.91314(13) 0.50463(10) 0.34801(7) 0.0256(3) Uani 1 1 d . . . . .
N3 N 0.84788(13) 0.56790(10) 0.30589(6) 0.0242(3) Uani 1 1 d . . . . .
N4 N 0.62356(15) 0.79113(12) 0.37865(8) 0.0333(3) Uani 1 1 d . . . . .
C1 C 0.2786(3) 0.5041(3) 0.25285(14) 0.0792(10) Uani 1 1 d . . . . .
H1A H 0.237334 0.470435 0.214544 0.119 Uiso 1 1 calc R U . . .
H1B H 0.370337 0.517061 0.242973 0.119 Uiso 1 1 calc R U . . .
H1C H 0.234987 0.570512 0.262084 0.119 Uiso 1 1 calc R U . . .
C2 C 0.2680(2) 0.4348(3) 0.31200(13) 0.0659(8) Uani 1 1 d . . . . .
H2A H 0.175646 0.417678 0.320113 0.079 Uiso 1 1 calc R U . . .
H2B H 0.315178 0.368916 0.303430 0.079 Uiso 1 1 calc R U . . .
C3 C 0.45178(17) 0.48025(14) 0.37684(9) 0.0302(4) Uani 1 1 d . . . . .
C4 C 0.49412(16) 0.54589(12) 0.43253(8) 0.0263(3) Uani 1 1 d . . . . .
C5 C 0.42117(16) 0.58793(13) 0.48236(9) 0.0303(4) Uani 1 1 d . . . . .
H5A H 0.330207 0.579749 0.488163 0.036 Uiso 1 1 calc R U . . .
C6 C 0.50563(17) 0.64613(13) 0.52402(8) 0.0277(3) Uani 1 1 d . . . . .
C7 C 0.63130(16) 0.63581(12) 0.49769(7) 0.0249(3) Uani 1 1 d . . . . .
C8 C 0.73851(18) 0.68420(14) 0.52579(9) 0.0319(4) Uani 1 1 d . . . . .
H8A H 0.823010 0.676078 0.507579 0.038 Uiso 1 1 calc R U . . .
C9 C 0.7167(2) 0.74484(15) 0.58157(9) 0.0364(4) Uani 1 1 d . . . . .
H9A H 0.788049 0.778929 0.602144 0.044 Uiso 1 1 calc R U . . .
C10 C 0.5924(2) 0.75739(15) 0.60855(9) 0.0372(4) Uani 1 1 d . . . . .
H10A H 0.581103 0.800265 0.646639 0.045 Uiso 1 1 calc R U . . .
C11 C 0.48620(19) 0.70871(15) 0.58088(9) 0.0352(4) Uani 1 1 d . . . . .
H11A H 0.402121 0.717018 0.599566 0.042 Uiso 1 1 calc R U . . .
C21 C 0.83900(16) 0.49748(12) 0.40246(8) 0.0238(3) Uani 1 1 d . . . . .
C22 C 0.72681(15) 0.55970(12) 0.39529(8) 0.0229(3) Uani 1 1 d . . . . .
C23 C 0.73568(15) 0.60448(12) 0.33280(8) 0.0231(3) Uani 1 1 d . . . . .
C24 C 0.64128(16) 0.66396(12) 0.29125(8) 0.0255(3) Uani 1 1 d . . . . .
C25 C 0.57420(16) 0.75538(12) 0.32148(8) 0.0260(3) Uani 1 1 d . . . . .
C26 C 0.47152(17) 0.80195(14) 0.28801(9) 0.0316(4) Uani 1 1 d . . . . .
H26A H 0.438779 0.773165 0.247844 0.038 Uiso 1 1 calc R U . . .
C27 C 0.41836(19) 0.89163(15) 0.31499(11) 0.0403(4) Uani 1 1 d . . . . .
H27A H 0.349356 0.926809 0.293093 0.048 Uiso 1 1 calc R U . . .
C28 C 0.4672(2) 0.92895(15) 0.37409(11) 0.0432(5) Uani 1 1 d . . . . .
H28A H 0.431897 0.989932 0.393903 0.052 Uiso 1 1 calc R U . . .
C29 C 0.5689(2) 0.87607(15) 0.40422(10) 0.0412(4) Uani 1 1 d . . . . .
H29A H 0.601130 0.901886 0.445304 0.049 Uiso 1 1 calc R U . . .
C41 C 0.88108(17) 0.43095(12) 0.45844(8) 0.0266(3) Uani 1 1 d . . . . .
C42 C 1.01368(18) 0.41435(14) 0.46922(9) 0.0327(4) Uani 1 1 d . . . . .
H42A H 1.075858 0.447910 0.441662 0.039 Uiso 1 1 calc R U . . .
C43 C 1.0546(2) 0.34901(15) 0.52006(10) 0.0407(4) Uani 1 1 d . . . . .
H43A H 1.144653 0.337029 0.526654 0.049 Uiso 1 1 calc R U . . .
C44 C 0.9647(2) 0.30106(15) 0.56130(10) 0.0443(5) Uani 1 1 d . . . . .
H44A H 0.993146 0.256807 0.596269 0.053 Uiso 1 1 calc R U . . .
C45 C 0.8341(2) 0.31778(15) 0.55144(10) 0.0432(5) Uani 1 1 d . . . . .
H45A H 0.772597 0.285072 0.579812 0.052 Uiso 1 1 calc R U . . .
C46 C 0.79139(19) 0.38231(14) 0.50016(9) 0.0340(4) Uani 1 1 d . . . . .
H46A H 0.701068 0.393202 0.493594 0.041 Uiso 1 1 calc R U . . .
C51 C 0.90816(15) 0.60042(13) 0.24508(8) 0.0251(3) Uani 1 1 d . . . . .
C52 C 0.94184(18) 0.52714(14) 0.19788(9) 0.0338(4) Uani 1 1 d . . . . .
H52A H 0.924220 0.455248 0.204914 0.041 Uiso 1 1 calc R U . . .
C53 C 1.0020(2) 0.56059(17) 0.13990(9) 0.0432(4) Uani 1 1 d . . . . .
H53A H 1.025430 0.510897 0.106985 0.052 Uiso 1 1 calc R U . . .
C54 C 1.0283(2) 0.66475(17) 0.12928(9) 0.0415(4) Uani 1 1 d . . . . .
H54A H 1.069510 0.686495 0.089356 0.050 Uiso 1 1 calc R U . . .
C55 C 0.9944(2) 0.73747(15) 0.17715(9) 0.0380(4) Uani 1 1 d . . . . .
H55A H 1.012712 0.809272 0.170248 0.046 Uiso 1 1 calc R U . . .
C56 C 0.93377(17) 0.70541(13) 0.23501(9) 0.0309(4) Uani 1 1 d . . . . .
H56A H 0.909738 0.755189 0.267761 0.037 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 C3 1.343(2) . ?
O1 C2 1.456(3) . ?
O2 C3 1.200(2) . ?
O3 C24 1.215(2) . ?
N1 C7 1.392(2) . ?
N1 C4 1.395(2) . ?
N1 C22 1.417(2) . ?
N2 C21 1.338(2) . ?
N2 N3 1.3518(19) . ?
N3 C23 1.360(2) . ?
N3 C51 1.434(2) . ?
N4 C29 1.330(2) . ?
N4 C25 1.338(2) . ?
C1 C2 1.489(5) . ?
C3 C4 1.467(2) . ?
C4 C5 1.364(2) . ?
C5 C6 1.420(2) . ?
C6 C7 1.405(2) . ?
C6 C11 1.411(2) . ?
C7 C8 1.387(3) . ?
C8 C9 1.383(3) . ?
C9 C10 1.400(3) . ?
C10 C11 1.377(3) . ?
C21 C22 1.412(2) . ?
C21 C41 1.478(2) . ?
C22 C23 1.385(2) . ?
C23 C24 1.492(2) . ?
C24 C25 1.490(2) . ?
C25 C26 1.389(2) . ?
C26 C27 1.384(3) . ?
C27 C28 1.377(3) . ?
C28 C29 1.387(3) . ?
C41 C46 1.395(3) . ?
C41 C42 1.399(3) . ?
C42 C43 1.387(3) . ?
C43 C44 1.387(3) . ?
C44 C45 1.376(3) . ?
C45 C46 1.393(3) . ?
C51 C52 1.380(2) . ?
C51 C56 1.387(2) . ?
C52 C53 1.388(3) . ?
C53 C54 1.379(3) . ?
C54 C55 1.385(3) . ?
C55 C56 1.383(3) . ?

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
C3 O1 C2 115.79(16) . . ?
C7 N1 C4 107.41(13) . . ?
C7 N1 C22 124.21(13) . . ?
C4 N1 C22 127.12(13) . . ?
C21 N2 N3 105.67(12) . . ?
N2 N3 C23 112.35(13) . . ?
N2 N3 C51 119.58(13) . . ?
C23 N3 C51 127.40(13) . . ?
C29 N4 C25 116.87(16) . . ?
O1 C2 C1 110.5(2) . . ?
O2 C3 O1 124.71(17) . . ?
O2 C3 C4 125.48(16) . . ?
O1 C3 C4 109.80(15) . . ?
C5 C4 N1 109.68(14) . . ?
C5 C4 C3 128.60(16) . . ?
N1 C4 C3 121.71(14) . . ?
C4 C5 C6 107.68(15) . . ?
C7 C6 C11 119.32(16) . . ?
C7 C6 C5 107.02(14) . . ?
C11 C6 C5 133.63(17) . . ?
C8 C7 N1 129.27(15) . . ?
C8 C7 C6 122.54(15) . . ?
N1 C7 C6 108.19(14) . . ?
C9 C8 C7 116.90(17) . . ?
C8 C9 C10 121.84(17) . . ?
C11 C10 C9 121.19(16) . . ?
C10 C11 C6 118.20(17) . . ?
N2 C21 C22 110.18(14) . . ?
N2 C21 C41 119.71(14) . . ?
C22 C21 C41 130.11(15) . . ?
C23 C22 C21 105.84(13) . . ?
C23 C22 N1 126.37(14) . . ?
C21 C22 N1 127.78(14) . . ?
N3 C23 C22 105.92(13) . . ?
N3 C23 C24 120.50(14) . . ?
C22 C23 C24 132.63(14) . . ?
O3 C24 C25 121.69(15) . . ?
O3 C24 C23 119.86(15) . . ?
C25 C24 C23 118.41(14) . . ?
N4 C25 C26 123.96(16) . . ?
N4 C25 C24 116.34(15) . . ?
C26 C25 C24 119.58(16) . . ?
C27 C26 C25 117.94(18) . . ?
C28 C27 C26 118.85(18) . . ?
C27 C28 C29 118.91(18) . . ?
N4 C29 C28 123.45(19) . . ?
C46 C41 C42 119.03(16) . . ?
C46 C41 C21 121.47(16) . . ?
C42 C41 C21 119.48(16) . . ?
C43 C42 C41 120.15(18) . . ?
C44 C43 C42 120.39(19) . . ?
C45 C44 C43 119.82(18) . . ?
C44 C45 C46 120.5(2) . . ?
C45 C46 C41 120.10(19) . . ?
C52 C51 C56 120.84(16) . . ?
C52 C51 N3 119.85(15) . . ?
C56 C51 N3 119.30(14) . . ?
C51 C52 C53 118.66(17) . . ?
C54 C53 C52 121.12(18) . . ?
C53 C54 C55 119.64(17) . . ?
C56 C55 C54 119.91(17) . . ?
C55 C56 C51 119.82(16) . . ?

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
C21 N2 N3 C23 2.11(17) . . . . ?
C21 N2 N3 C51 173.47(13) . . . . ?
C3 O1 C2 C1 -81.9(3) . . . . ?
C2 O1 C3 O2 -7.0(3) . . . . ?
C2 O1 C3 C4 172.5(2) . . . . ?
C7 N1 C4 C5 -1.35(18) . . . . ?
C22 N1 C4 C5 -168.83(15) . . . . ?
C7 N1 C4 C3 179.44(14) . . . . ?
C22 N1 C4 C3 12.0(2) . . . . ?
O2 C3 C4 C5 -165.23(18) . . . . ?
O1 C3 C4 C5 15.2(3) . . . . ?
O2 C3 C4 N1 13.8(3) . . . . ?
O1 C3 C4 N1 -165.72(16) . . . . ?
N1 C4 C5 C6 1.37(19) . . . . ?
C3 C4 C5 C6 -179.49(16) . . . . ?
C4 C5 C6 C7 -0.86(19) . . . . ?
C4 C5 C6 C11 177.37(18) . . . . ?
C4 N1 C7 C8 -178.24(16) . . . . ?
C22 N1 C7 C8 -10.3(3) . . . . ?
C4 N1 C7 C6 0.78(17) . . . . ?
C22 N1 C7 C6 168.72(14) . . . . ?
C11 C6 C7 C8 0.6(2) . . . . ?
C5 C6 C7 C8 179.13(15) . . . . ?
C11 C6 C7 N1 -178.50(14) . . . . ?
C5 C6 C7 N1 0.03(18) . . . . ?
N1 C7 C8 C9 178.45(16) . . . . ?
C6 C7 C8 C9 -0.4(2) . . . . ?
C7 C8 C9 C10 -0.2(3) . . . . ?
C8 C9 C10 C11 0.7(3) . . . . ?
C9 C10 C11 C6 -0.5(3) . . . . ?
C7 C6 C11 C10 -0.1(2) . . . . ?
C5 C6 C11 C10 -178.18(19) . . . . ?
N3 N2 C21 C22 -1.70(17) . . . . ?
N3 N2 C21 C41 178.42(14) . . . . ?
N2 C21 C22 C23 0.74(17) . . . . ?
C41 C21 C22 C23 -179.39(16) . . . . ?
N2 C21 C22 N1 179.63(15) . . . . ?
C41 C21 C22 N1 -0.5(3) . . . . ?
C7 N1 C22 C23 -104.07(19) . . . . ?
C4 N1 C22 C23 61.4(2) . . . . ?
C7 N1 C22 C21 77.3(2) . . . . ?
C4 N1 C22 C21 -117.23(19) . . . . ?
N2 N3 C23 C22 -1.66(17) . . . . ?
C51 N3 C23 C22 -172.19(15) . . . . ?
N2 N3 C23 C24 -171.87(13) . . . . ?
C51 N3 C23 C24 17.6(2) . . . . ?
C21 C22 C23 N3 0.53(17) . . . . ?
N1 C22 C23 N3 -178.38(14) . . . . ?
C21 C22 C23 C24 169.05(16) . . . . ?
N1 C22 C23 C24 -9.9(3) . . . . ?
N3 C23 C24 O3 37.3(2) . . . . ?
C22 C23 C24 O3 -129.88(19) . . . . ?
N3 C23 C24 C25 -140.69(15) . . . . ?
C22 C23 C24 C25 52.2(2) . . . . ?
C29 N4 C25 C26 0.5(3) . . . . ?
C29 N4 C25 C24 176.48(16) . . . . ?
O3 C24 C25 N4 -163.99(16) . . . . ?
C23 C24 C25 N4 13.9(2) . . . . ?
O3 C24 C25 C26 12.2(2) . . . . ?
C23 C24 C25 C26 -169.86(14) . . . . ?
N4 C25 C26 C27 1.0(3) . . . . ?
C24 C25 C26 C27 -174.93(15) . . . . ?
C25 C26 C27 C28 -1.5(3) . . . . ?
C26 C27 C28 C29 0.7(3) . . . . ?
C25 N4 C29 C28 -1.4(3) . . . . ?
C27 C28 C29 N4 0.9(3) . . . . ?
N2 C21 C41 C46 -150.06(16) . . . . ?
C22 C21 C41 C46 30.1(3) . . . . ?
N2 C21 C41 C42 28.6(2) . . . . ?
C22 C21 C41 C42 -151.27(17) . . . . ?
C46 C41 C42 C43 1.1(3) . . . . ?
C21 C41 C42 C43 -177.62(15) . . . . ?
C41 C42 C43 C44 -1.1(3) . . . . ?
C42 C43 C44 C45 0.5(3) . . . . ?
C43 C44 C45 C46 0.2(3) . . . . ?
C44 C45 C46 C41 -0.2(3) . . . . ?
C42 C41 C46 C45 -0.4(3) . . . . ?
C21 C41 C46 C45 178.27(16) . . . . ?
N2 N3 C51 C52 62.5(2) . . . . ?
C23 N3 C51 C52 -127.57(18) . . . . ?
N2 N3 C51 C56 -116.46(17) . . . . ?
C23 N3 C51 C56 53.5(2) . . . . ?
C56 C51 C52 C53 0.0(3) . . . . ?
N3 C51 C52 C53 -178.97(17) . . . . ?
C51 C52 C53 C54 0.2(3) . . . . ?
C52 C53 C54 C55 0.0(3) . . . . ?
C53 C54 C55 C56 -0.4(3) . . . . ?
C54 C55 C56 C51 0.5(3) . . . . ?
C52 C51 C56 C55 -0.3(3) . . . . ?
N3 C51 C56 C55 178.64(16) . . . . ?

_refine_diff_density_max         0.148
_refine_diff_density_min         -0.121
_refine_diff_density_rms         0.028


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Acetone, MeOH, DCM, Hexane'
####################################################################### 
# 
# 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_hqw027
_database_code_depnum_ccdc_archive 'CCDC 2467820'
loop_
_audit_author_name
_audit_author_address
'Yuqiao Zhou'
;College of Chemistry, Sichuan University, Chengdu, China
China
;
_audit_update_record             
;
2025-06-27 deposited with the CCDC.	2025-09-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/1
_shelx_SHELXL_version_number     2019/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C32 H26 N4 O3)'
_chemical_formula_sum            'C64 H52 N8 O6'
_chemical_formula_weight         1029.13

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           1
_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'

_cell_length_a                   9.4969(2)
_cell_length_b                   11.5694(3)
_cell_length_c                   12.2031(3)
_cell_angle_alpha                93.9470(10)
_cell_angle_beta                 96.9580(10)
_cell_angle_gamma                96.7230(10)
_cell_volume                     1317.07(5)
_cell_formula_units_Z            1
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    9098
_cell_measurement_theta_min      3.66
_cell_measurement_theta_max      80.13

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.298
_exptl_crystal_F_000             540
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.247
_exptl_crystal_size_mid          0.158
_exptl_crystal_size_min          0.067
_exptl_absorpt_coefficient_mu    0.683
_shelx_estimated_absorpt_T_min   0.849
_shelx_estimated_absorpt_T_max   0.956
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.8424
_exptl_absorpt_correction_T_max  0.9983
_exptl_absorpt_process_details   'SADABS (Krause et al., 2015)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 Venture Photon II'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            44167
_diffrn_reflns_av_unetI/netI     0.0310
_diffrn_reflns_av_R_equivalents  0.0379
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.662
_diffrn_reflns_theta_max         80.783
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.934
_diffrn_reflns_point_group_measured_fraction_full 0.976
_reflns_number_total             10814
_reflns_number_gt                10546
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.903
_reflns_Friedel_fraction_max     0.887
_reflns_Friedel_fraction_full    0.953

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

_computing_data_collection       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0336P)²+0.1675P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
; 
 Flack x determined using 4864 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.09(5)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         10814
_refine_ls_number_parameters     715
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0291
_refine_ls_R_factor_gt           0.0281
_refine_ls_wR_factor_ref         0.0717
_refine_ls_wR_factor_gt          0.0707
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.030
_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 0.04452(14) 0.32572(13) 0.49868(10) 0.0354(3) Uani 1 1 d . . . . .
O2X O 0.2531(8) 0.339(4) 0.4329(7) 0.080(6) Uani 0.59(7) 1 d D . P A 1
O2Y O 0.2390(16) 0.2888(16) 0.4228(12) 0.041(4) Uani 0.41(7) 1 d D . P A 2
O3A O 0.47194(15) 0.14352(16) 0.20538(14) 0.0503(4) Uani 1 1 d . . . . .
N1A N 0.08926(15) 0.33272(13) 0.20784(11) 0.0277(3) Uani 1 1 d . . . . .
N2A N 0.29678(17) 0.21240(14) 0.03161(12) 0.0309(3) Uani 1 1 d . . . . .
N3A N 0.33309(15) 0.32847(13) 0.02288(12) 0.0272(3) Uani 1 1 d . . . . .
N4A N 0.14083(16) 0.02590(14) 0.27885(13) 0.0325(3) Uani 1 1 d . . . . .
C1A C 0.0074(3) 0.3090(2) 0.68621(17) 0.0500(5) Uani 1 1 d . . . . .
H1AA H 0.052872 0.297226 0.760367 0.075 Uiso 1 1 calc R U . . .
H1AB H -0.070626 0.245787 0.662270 0.075 Uiso 1 1 calc R U . . .
H1AC H -0.031014 0.384064 0.688091 0.075 Uiso 1 1 calc R U . . .
C2A C 0.1154(3) 0.3090(3) 0.60675(17) 0.0544(6) Uani 1 1 d . . . . .
H2AA H 0.194599 0.372789 0.630069 0.065 Uiso 1 1 calc R U . . .
H2AB H 0.155674 0.233852 0.604838 0.065 Uiso 1 1 calc R U . . .
C3A C 0.1234(2) 0.3249(2) 0.41593(15) 0.0375(4) Uani 1 1 d D . . . .
C4A C 0.03627(18) 0.33475(15) 0.30965(14) 0.0274(3) Uani 1 1 d . . . . .
C5A C -0.10782(19) 0.34200(16) 0.29335(14) 0.0288(3) Uani 1 1 d . . . . .
H5AA H -0.168881 0.346183 0.349282 0.035 Uiso 1 1 calc R U . . .
C6A C -0.14895(18) 0.34213(15) 0.17754(14) 0.0275(3) Uani 1 1 d . . . . .
C7A C -0.02464(18) 0.33487(15) 0.12609(14) 0.0262(3) Uani 1 1 d . . . . .
C8A C -0.0292(2) 0.33096(18) 0.01035(15) 0.0324(4) Uani 1 1 d . . . . .
H8AA H 0.054278 0.325219 -0.024328 0.039 Uiso 1 1 calc R U . . .
C9A C -0.1604(2) 0.33580(19) -0.05092(16) 0.0366(4) Uani 1 1 d . . . . .
H9AA H -0.166662 0.333833 -0.129329 0.044 Uiso 1 1 calc R U . . .
C10A C -0.2849(2) 0.34356(19) -0.00059(17) 0.0381(4) Uani 1 1 d . . . . .
H10A H -0.373173 0.346634 -0.045475 0.046 Uiso 1 1 calc R U . . .
C11A C -0.28087(19) 0.34676(17) 0.11246(16) 0.0336(4) Uani 1 1 d . . . . .
H11A H -0.365310 0.351984 0.146072 0.040 Uiso 1 1 calc R U . . .
C21A C 0.24053(18) 0.18794(15) 0.13482(13) 0.0274(3) Uani 1 1 d . . . . .
H21A H 0.143574 0.141428 0.120415 0.033 Uiso 1 1 calc R U . . .
C22A C 0.23382(17) 0.31184(16) 0.18959(14) 0.0276(3) Uani 1 1 d . . . . .
H22A H 0.296739 0.322772 0.262366 0.033 Uiso 1 1 calc R U . . .
C23A C 0.30226(17) 0.38836(16) 0.10844(14) 0.0268(3) Uani 1 1 d . . . . .
C24A C 0.33515(18) 0.51531(16) 0.12356(15) 0.0310(4) Uani 1 1 d . . . . .
C25A C 0.4133(2) 0.57576(17) 0.05112(16) 0.0342(4) Uani 1 1 d . . . . .
H25A H 0.450166 0.533503 -0.006180 0.041 Uiso 1 1 calc R U . . .
C26A C 0.4379(2) 0.69637(19) 0.06162(19) 0.0422(5) Uani 1 1 d . . . . .
H26A H 0.490449 0.736317 0.011102 0.051 Uiso 1 1 calc R U . . .
C27A C 0.3864(2) 0.7592(2) 0.1452(2) 0.0531(6) Uani 1 1 d . . . . .
H27A H 0.401724 0.842118 0.151463 0.064 Uiso 1 1 calc R U . . .
C28A C 0.3134(3) 0.7009(3) 0.2187(3) 0.0705(9) Uani 1 1 d . . . . .
H28A H 0.279542 0.743846 0.277128 0.085 Uiso 1 1 calc R U . . .
C29A C 0.2878(3) 0.5797(2) 0.2091(2) 0.0563(6) Uani 1 1 d . . . . .
H29A H 0.237627 0.540599 0.261384 0.068 Uiso 1 1 calc R U . . .
C31A C 0.34451(19) 0.12711(17) 0.20981(15) 0.0304(3) Uani 1 1 d . . . . .
C32A C 0.28371(18) 0.05297(15) 0.29290(13) 0.0266(3) Uani 1 1 d . . . . .
C33A C 0.37404(19) 0.01633(16) 0.37804(14) 0.0292(3) Uani 1 1 d . . . . .
H33A H 0.474633 0.036924 0.383745 0.035 Uiso 1 1 calc R U . . .
C34A C 0.3146(2) -0.05097(17) 0.45467(15) 0.0338(4) Uani 1 1 d . . . . .
H34A H 0.373122 -0.077421 0.514190 0.041 Uiso 1 1 calc R U . . .
C35A C 0.1680(2) -0.07825(18) 0.44170(17) 0.0375(4) Uani 1 1 d . . . . .
H35A H 0.123391 -0.123239 0.493186 0.045 Uiso 1 1 calc R U . . .
C36A C 0.0860(2) -0.03958(18) 0.35303(18) 0.0379(4) Uani 1 1 d . . . . .
H36A H -0.014642 -0.060833 0.344601 0.045 Uiso 1 1 calc R U . . .
C41A C 0.28779(19) 0.12975(16) -0.05844(14) 0.0288(3) Uani 1 1 d . . . . .
C42A C 0.2552(2) 0.01179(18) -0.04347(16) 0.0375(4) Uani 1 1 d . . . . .
H42A H 0.242303 -0.011551 0.028159 0.045 Uiso 1 1 calc R U . . .
C43A C 0.2413(3) -0.0716(2) -0.13234(19) 0.0453(5) Uani 1 1 d . . . . .
H43A H 0.217744 -0.151706 -0.121388 0.054 Uiso 1 1 calc R U . . .
C44A C 0.2615(3) -0.0395(2) -0.23666(18) 0.0469(5) Uani 1 1 d . . . . .
H44A H 0.251235 -0.096769 -0.297670 0.056 Uiso 1 1 calc R U . . .
C45A C 0.2970(2) 0.0776(2) -0.25116(17) 0.0427(5) Uani 1 1 d . . . . .
H45A H 0.313133 0.100020 -0.322499 0.051 Uiso 1 1 calc R U . . .
C46A C 0.3095(2) 0.16251(18) -0.16371(15) 0.0347(4) Uani 1 1 d . . . . .
H46A H 0.332713 0.242508 -0.175232 0.042 Uiso 1 1 calc R U . . .
O1B O 0.91236(14) 0.65217(13) 1.05513(10) 0.0360(3) Uani 1 1 d . . . . .
O2B O 0.71239(14) 0.63234(14) 0.93308(11) 0.0388(3) Uani 1 1 d . . . . .
O3B O 0.56916(17) 0.90003(16) 0.67443(12) 0.0482(4) Uani 1 1 d . . . . .
N1B N 0.90036(15) 0.64681(13) 0.75725(11) 0.0269(3) Uani 1 1 d . . . . .
N2B N 0.74704(19) 0.79153(14) 0.55265(12) 0.0339(3) Uani 1 1 d . . . . .
N3B N 0.68683(16) 0.67897(13) 0.51957(12) 0.0295(3) Uani 1 1 d . . . . .
N4B N 0.85258(18) 0.90150(16) 0.88875(13) 0.0374(4) Uani 1 1 d . . . . .
C1B C 0.9205(3) 0.6554(2) 1.25127(17) 0.0479(5) Uani 1 1 d . . . . .
H1BA H 0.864442 0.659020 1.313492 0.072 Uiso 1 1 calc R U . . .
H1BB H 0.995604 0.722362 1.260136 0.072 Uiso 1 1 calc R U . . .
H1BC H 0.964240 0.582823 1.249713 0.072 Uiso 1 1 calc R U . . .
C2B C 0.8238(2) 0.6587(2) 1.14423(15) 0.0397(4) Uani 1 1 d . . . . .
H2BA H 0.746809 0.591924 1.134534 0.048 Uiso 1 1 calc R U . . .
H2BB H 0.779448 0.732026 1.144427 0.048 Uiso 1 1 calc R U . . .
C3B C 0.84135(19) 0.63961(16) 0.95259(14) 0.0294(3) Uani 1 1 d . . . . .
C4B C 0.94105(18) 0.63540(15) 0.86935(14) 0.0279(3) Uani 1 1 d . . . . .
C5B C 1.08141(19) 0.61796(17) 0.88647(16) 0.0328(4) Uani 1 1 d . . . . .
H5BA H 1.134170 0.606486 0.955264 0.039 Uiso 1 1 calc R U . . .
C6B C 1.1343(2) 0.62015(17) 0.78199(16) 0.0336(4) Uani 1 1 d . . . . .
C7B C 1.01955(19) 0.63919(15) 0.70312(15) 0.0294(3) Uani 1 1 d . . . . .
C8B C 1.0363(2) 0.64848(18) 0.59125(17) 0.0371(4) Uani 1 1 d . . . . .
H8BA H 0.959069 0.661917 0.538522 0.045 Uiso 1 1 calc R U . . .
C9B C 1.1693(3) 0.6373(2) 0.56121(19) 0.0475(5) Uani 1 1 d . . . . .
H9BA H 1.183447 0.642287 0.485849 0.057 Uiso 1 1 calc R U . . .
C10B C 1.2852(3) 0.6186(3) 0.6386(2) 0.0555(6) Uani 1 1 d . . . . .
H10B H 1.375791 0.612180 0.614770 0.067 Uiso 1 1 calc R U . . .
C11B C 1.2690(2) 0.6097(2) 0.7479(2) 0.0480(5) Uani 1 1 d . . . . .
H11B H 1.347353 0.596708 0.799780 0.058 Uiso 1 1 calc R U . . .
C21B C 0.78533(19) 0.81218(15) 0.67196(13) 0.0280(3) Uani 1 1 d . . . . .
H21B H 0.886320 0.850091 0.691155 0.034 Uiso 1 1 calc R U . . .
C22B C 0.76756(17) 0.68632(15) 0.71036(13) 0.0260(3) Uani 1 1 d . . . . .
H22B H 0.698593 0.682060 0.766150 0.031 Uiso 1 1 calc R U . . .
C23B C 0.69784(18) 0.61686(15) 0.60322(13) 0.0272(3) Uani 1 1 d . . . . .
C24B C 0.65112(18) 0.49104(16) 0.59400(14) 0.0282(3) Uani 1 1 d . . . . .
C25B C 0.6361(2) 0.43228(17) 0.68910(15) 0.0334(4) Uani 1 1 d . . . . .
H25B H 0.654563 0.474210 0.760117 0.040 Uiso 1 1 calc R U . . .
C26B C 0.5940(2) 0.31219(19) 0.67958(17) 0.0390(4) Uani 1 1 d . . . . .
H26B H 0.583102 0.272544 0.744264 0.047 Uiso 1 1 calc R U . . .
C27B C 0.5679(2) 0.25039(18) 0.57679(19) 0.0413(4) Uani 1 1 d . . . . .
H27B H 0.540810 0.168296 0.570859 0.050 Uiso 1 1 calc R U . . .
C28B C 0.5814(2) 0.30833(18) 0.48249(17) 0.0390(4) Uani 1 1 d . . . . .
H28B H 0.562522 0.265829 0.411754 0.047 Uiso 1 1 calc R U . . .
C29B C 0.6222(2) 0.42762(17) 0.49030(15) 0.0329(4) Uani 1 1 d . . . . .
H29B H 0.630623 0.466663 0.424971 0.039 Uiso 1 1 calc R U . . .
C31B C 0.6817(2) 0.88432(16) 0.72459(14) 0.0313(4) Uani 1 1 d . . . . .
C32B C 0.7281(2) 0.93103(16) 0.84275(15) 0.0308(4) Uani 1 1 d . . . . .
C33B C 0.6446(3) 0.99950(19) 0.89838(17) 0.0415(4) Uani 1 1 d . . . . .
H33B H 0.555800 1.017175 0.863104 0.050 Uiso 1 1 calc R U . . .
C34B C 0.6945(3) 1.0415(2) 1.00725(18) 0.0483(5) Uani 1 1 d . . . . .
H34B H 0.640507 1.088944 1.048097 0.058 Uiso 1 1 calc R U . . .
C35B C 0.8235(3) 1.0132(2) 1.05484(16) 0.0449(5) Uani 1 1 d . . . . .
H35B H 0.861175 1.042463 1.128508 0.054 Uiso 1 1 calc R U . . .
C36B C 0.8974(2) 0.9416(2) 0.99371(17) 0.0437(5) Uani 1 1 d . . . . .
H36B H 0.984390 0.919836 1.028276 0.052 Uiso 1 1 calc R U . . .
C41B C 0.74442(19) 0.87795(16) 0.47909(14) 0.0286(3) Uani 1 1 d . . . . .
C42B C 0.68745(18) 0.85164(16) 0.36817(14) 0.0289(3) Uani 1 1 d . . . . .
H42B H 0.647206 0.774169 0.341940 0.035 Uiso 1 1 calc R U . . .
C43B C 0.69009(19) 0.93958(17) 0.29653(15) 0.0323(4) Uani 1 1 d . . . . .
H43B H 0.652079 0.921315 0.220840 0.039 Uiso 1 1 calc R U . . .
C44B C 0.7468(2) 1.05333(17) 0.33274(15) 0.0328(4) Uani 1 1 d . . . . .
H44B H 0.747441 1.112717 0.282714 0.039 Uiso 1 1 calc R U . . .
C45B C 0.8025(2) 1.07918(17) 0.44267(16) 0.0353(4) Uani 1 1 d . . . . .
H45B H 0.841213 1.157134 0.468393 0.042 Uiso 1 1 calc R U . . .
C46B C 0.8027(2) 0.99280(17) 0.51610(15) 0.0345(4) Uani 1 1 d . . . . .
H46B H 0.842307 1.011556 0.591388 0.041 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
O1A C3A 1.329(2) . ?
O1A C2A 1.442(2) . ?
O2X C3A 1.213(8) . ?
O2Y C3A 1.214(9) . ?
O3A C31A 1.211(2) . ?
N1A C7A 1.383(2) . ?
N1A C4A 1.396(2) . ?
N1A C22A 1.462(2) . ?
N2A N3A 1.362(2) . ?
N2A C41A 1.394(2) . ?
N2A C21A 1.459(2) . ?
N3A C23A 1.295(2) . ?
N4A C36A 1.334(2) . ?
N4A C32A 1.344(2) . ?
C1A C2A 1.495(3) . ?
C3A C4A 1.471(2) . ?
C4A C5A 1.372(2) . ?
C5A C6A 1.420(2) . ?
C6A C11A 1.408(2) . ?
C6A C7A 1.411(2) . ?
C7A C8A 1.405(2) . ?
C8A C9A 1.382(3) . ?
C9A C10A 1.405(3) . ?
C10A C11A 1.373(3) . ?
C21A C31A 1.530(2) . ?
C21A C22A 1.551(2) . ?
C22A C23A 1.526(2) . ?
C23A C24A 1.459(3) . ?
C24A C29A 1.390(3) . ?
C24A C25A 1.394(3) . ?
C25A C26A 1.382(3) . ?
C26A C27A 1.382(3) . ?
C27A C28A 1.365(4) . ?
C28A C29A 1.389(4) . ?
C31A C32A 1.498(2) . ?
C32A C33A 1.387(2) . ?
C33A C34A 1.387(3) . ?
C34A C35A 1.379(3) . ?
C35A C36A 1.386(3) . ?
C41A C42A 1.393(3) . ?
C41A C46A 1.396(2) . ?
C42A C43A 1.384(3) . ?
C43A C44A 1.380(3) . ?
C44A C45A 1.386(3) . ?
C45A C46A 1.384(3) . ?
O1B C3B 1.338(2) . ?
O1B C2B 1.456(2) . ?
O2B C3B 1.211(2) . ?
O3B C31B 1.205(2) . ?
N1B C7B 1.386(2) . ?
N1B C4B 1.395(2) . ?
N1B C22B 1.457(2) . ?
N2B N3B 1.372(2) . ?
N2B C41B 1.389(2) . ?
N2B C21B 1.453(2) . ?
N3B C23B 1.289(2) . ?
N4B C36B 1.333(3) . ?
N4B C32B 1.338(3) . ?
C1B C2B 1.508(3) . ?
C3B C4B 1.472(2) . ?
C4B C5B 1.365(3) . ?
C5B C6B 1.426(3) . ?
C6B C11B 1.408(3) . ?
C6B C7B 1.412(3) . ?
C7B C8B 1.403(3) . ?
C8B C9B 1.375(3) . ?
C9B C10B 1.408(4) . ?
C10B C11B 1.370(4) . ?
C21B C31B 1.533(2) . ?
C21B C22B 1.557(2) . ?
C22B C23B 1.522(2) . ?
C23B C24B 1.464(2) . ?
C24B C25B 1.398(2) . ?
C24B C29B 1.399(2) . ?
C25B C26B 1.393(3) . ?
C26B C27B 1.381(3) . ?
C27B C28B 1.383(3) . ?
C28B C29B 1.383(3) . ?
C31B C32B 1.500(2) . ?
C32B C33B 1.386(3) . ?
C33B C34B 1.390(3) . ?
C34B C35B 1.375(4) . ?
C35B C36B 1.384(3) . ?
C41B C42B 1.395(2) . ?
C41B C46B 1.400(3) . ?
C42B C43B 1.386(2) . ?
C43B C44B 1.383(3) . ?
C44B C45B 1.380(3) . ?
C45B C46B 1.387(3) . ?

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
C3A O1A C2A 116.58(16) . . ?
C7A N1A C4A 107.75(13) . . ?
C7A N1A C22A 125.80(14) . . ?
C4A N1A C22A 125.69(14) . . ?
N3A N2A C41A 121.98(14) . . ?
N3A N2A C21A 113.16(13) . . ?
C41A N2A C21A 123.66(15) . . ?
C23A N3A N2A 109.80(14) . . ?
C36A N4A C32A 116.41(15) . . ?
O1A C2A C1A 107.89(19) . . ?
O2X C3A O1A 121.5(4) . . ?
O2Y C3A O1A 123.0(5) . . ?
O2X C3A C4A 125.7(6) . . ?
O2Y C3A C4A 123.1(7) . . ?
O1A C3A C4A 111.02(16) . . ?
C5A C4A N1A 109.49(15) . . ?
C5A C4A C3A 126.53(15) . . ?
N1A C4A C3A 123.92(15) . . ?
C4A C5A C6A 107.46(15) . . ?
C11A C6A C7A 119.84(16) . . ?
C11A C6A C5A 133.14(16) . . ?
C7A C6A C5A 107.01(14) . . ?
N1A C7A C8A 130.34(15) . . ?
N1A C7A C6A 108.25(14) . . ?
C8A C7A C6A 121.41(15) . . ?
C9A C8A C7A 117.19(17) . . ?
C8A C9A C10A 121.92(17) . . ?
C11A C10A C9A 121.02(17) . . ?
C10A C11A C6A 118.61(17) . . ?
N2A C21A C31A 111.01(14) . . ?
N2A C21A C22A 102.75(13) . . ?
C31A C21A C22A 108.73(14) . . ?
N1A C22A C23A 115.33(14) . . ?
N1A C22A C21A 113.24(14) . . ?
C23A C22A C21A 101.21(13) . . ?
N3A C23A C24A 121.81(15) . . ?
N3A C23A C22A 112.83(15) . . ?
C24A C23A C22A 125.34(15) . . ?
C29A C24A C25A 118.00(19) . . ?
C29A C24A C23A 121.26(18) . . ?
C25A C24A C23A 120.73(16) . . ?
C26A C25A C24A 120.83(19) . . ?
C27A C26A C25A 120.4(2) . . ?
C28A C27A C26A 119.4(2) . . ?
C27A C28A C29A 120.9(2) . . ?
C28A C29A C24A 120.5(2) . . ?
O3A C31A C32A 121.62(16) . . ?
O3A C31A C21A 120.76(16) . . ?
C32A C31A C21A 117.52(14) . . ?
N4A C32A C33A 123.88(16) . . ?
N4A C32A C31A 116.16(15) . . ?
C33A C32A C31A 119.95(15) . . ?
C34A C33A C32A 118.71(17) . . ?
C35A C34A C33A 117.89(17) . . ?
C34A C35A C36A 119.53(17) . . ?
N4A C36A C35A 123.56(18) . . ?
C42A C41A N2A 119.35(16) . . ?
C42A C41A C46A 119.14(17) . . ?
N2A C41A C46A 121.50(16) . . ?
C43A C42A C41A 120.40(18) . . ?
C44A C43A C42A 120.6(2) . . ?
C43A C44A C45A 119.03(19) . . ?
C46A C45A C44A 121.27(19) . . ?
C45A C46A C41A 119.53(18) . . ?
C3B O1B C2B 115.35(15) . . ?
C7B N1B C4B 107.68(14) . . ?
C7B N1B C22B 125.35(14) . . ?
C4B N1B C22B 125.58(14) . . ?
N3B N2B C41B 120.88(14) . . ?
N3B N2B C21B 113.01(14) . . ?
C41B N2B C21B 125.08(15) . . ?
C23B N3B N2B 109.11(14) . . ?
C36B N4B C32B 117.25(18) . . ?
O1B C2B C1B 106.97(18) . . ?
O2B C3B O1B 123.49(16) . . ?
O2B C3B C4B 125.75(15) . . ?
O1B C3B C4B 110.76(15) . . ?
C5B C4B N1B 109.87(15) . . ?
C5B C4B C3B 127.26(16) . . ?
N1B C4B C3B 122.85(15) . . ?
C4B C5B C6B 107.36(16) . . ?
C11B C6B C7B 119.39(18) . . ?
C11B C6B C5B 133.64(19) . . ?
C7B C6B C5B 106.95(16) . . ?
N1B C7B C8B 130.23(17) . . ?
N1B C7B C6B 108.11(15) . . ?
C8B C7B C6B 121.66(17) . . ?
C9B C8B C7B 117.15(19) . . ?
C8B C9B C10B 122.1(2) . . ?
C11B C10B C9B 120.8(2) . . ?
C10B C11B C6B 118.9(2) . . ?
N2B C21B C31B 111.59(14) . . ?
N2B C21B C22B 102.43(13) . . ?
C31B C21B C22B 109.41(14) . . ?
N1B C22B C23B 113.85(14) . . ?
N1B C22B C21B 114.45(14) . . ?
C23B C22B C21B 100.86(13) . . ?
N3B C23B C24B 122.66(15) . . ?
N3B C23B C22B 113.49(15) . . ?
C24B C23B C22B 123.82(14) . . ?
C25B C24B C29B 119.02(16) . . ?
C25B C24B C23B 120.35(16) . . ?
C29B C24B C23B 120.63(16) . . ?
C26B C25B C24B 119.92(17) . . ?
C27B C26B C25B 120.44(19) . . ?
C26B C27B C28B 119.81(19) . . ?
C29B C28B C27B 120.54(18) . . ?
C28B C29B C24B 120.26(17) . . ?
O3B C31B C32B 122.60(17) . . ?
O3B C31B C21B 121.79(16) . . ?
C32B C31B C21B 115.60(15) . . ?
N4B C32B C33B 123.63(17) . . ?
N4B C32B C31B 115.56(16) . . ?
C33B C32B C31B 120.81(17) . . ?
C32B C33B C34B 118.0(2) . . ?
C35B C34B C33B 118.8(2) . . ?
C34B C35B C36B 118.95(19) . . ?
N4B C36B C35B 123.3(2) . . ?
N2B C41B C42B 121.01(16) . . ?
N2B C41B C46B 119.61(15) . . ?
C42B C41B C46B 119.37(16) . . ?
C43B C42B C41B 119.39(16) . . ?
C44B C43B C42B 121.50(17) . . ?
C45B C44B C43B 118.97(16) . . ?
C44B C45B C46B 120.85(18) . . ?
C45B C46B C41B 119.92(17) . . ?

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
C41A N2A N3A C23A 165.32(16) . . . . ?
C21A N2A N3A C23A -2.5(2) . . . . ?
C3A O1A C2A C1A -178.2(2) . . . . ?
C2A O1A C3A O2X -18(3) . . . . ?
C2A O1A C3A O2Y 14.9(13) . . . . ?
C2A O1A C3A C4A 176.15(19) . . . . ?
C7A N1A C4A C5A -2.0(2) . . . . ?
C22A N1A C4A C5A -172.43(16) . . . . ?
C7A N1A C4A C3A 175.42(17) . . . . ?
C22A N1A C4A C3A 5.0(3) . . . . ?
O2X C3A C4A C5A -166(3) . . . . ?
O2Y C3A C4A C5A 160.2(12) . . . . ?
O1A C3A C4A C5A -1.1(3) . . . . ?
O2X C3A C4A N1A 17(3) . . . . ?
O2Y C3A C4A N1A -16.8(12) . . . . ?
O1A C3A C4A N1A -178.02(17) . . . . ?
N1A C4A C5A C6A 1.3(2) . . . . ?
C3A C4A C5A C6A -176.05(18) . . . . ?
C4A C5A C6A C11A 179.28(19) . . . . ?
C4A C5A C6A C7A -0.1(2) . . . . ?
C4A N1A C7A C8A -178.06(19) . . . . ?
C22A N1A C7A C8A -7.6(3) . . . . ?
C4A N1A C7A C6A 1.89(19) . . . . ?
C22A N1A C7A C6A 172.34(16) . . . . ?
C11A C6A C7A N1A 179.41(16) . . . . ?
C5A C6A C7A N1A -1.13(19) . . . . ?
C11A C6A C7A C8A -0.6(3) . . . . ?
C5A C6A C7A C8A 178.82(17) . . . . ?
N1A C7A C8A C9A -179.37(18) . . . . ?
C6A C7A C8A C9A 0.7(3) . . . . ?
C7A C8A C9A C10A -0.4(3) . . . . ?
C8A C9A C10A C11A 0.1(3) . . . . ?
C9A C10A C11A C6A 0.0(3) . . . . ?
C7A C6A C11A C10A 0.3(3) . . . . ?
C5A C6A C11A C10A -179.0(2) . . . . ?
N3A N2A C21A C31A -111.33(17) . . . . ?
C41A N2A C21A C31A 81.0(2) . . . . ?
N3A N2A C21A C22A 4.74(18) . . . . ?
C41A N2A C21A C22A -162.89(16) . . . . ?
C7A N1A C22A C23A 51.8(2) . . . . ?
C4A N1A C22A C23A -139.40(17) . . . . ?
C7A N1A C22A C21A -64.1(2) . . . . ?
C4A N1A C22A C21A 104.67(19) . . . . ?
N2A C21A C22A N1A 119.34(15) . . . . ?
C31A C21A C22A N1A -122.95(15) . . . . ?
N2A C21A C22A C23A -4.69(16) . . . . ?
C31A C21A C22A C23A 113.01(14) . . . . ?
N2A N3A C23A C24A 177.41(15) . . . . ?
N2A N3A C23A C22A -1.02(19) . . . . ?
N1A C22A C23A N3A -118.83(16) . . . . ?
C21A C22A C23A N3A 3.77(18) . . . . ?
N1A C22A C23A C24A 62.8(2) . . . . ?
C21A C22A C23A C24A -174.59(15) . . . . ?
N3A C23A C24A C29A 172.9(2) . . . . ?
C22A C23A C24A C29A -8.9(3) . . . . ?
N3A C23A C24A C25A -6.0(3) . . . . ?
C22A C23A C24A C25A 172.18(16) . . . . ?
C29A C24A C25A C26A -2.5(3) . . . . ?
C23A C24A C25A C26A 176.43(17) . . . . ?
C24A C25A C26A C27A 0.7(3) . . . . ?
C25A C26A C27A C28A 1.2(4) . . . . ?
C26A C27A C28A C29A -1.3(5) . . . . ?
C27A C28A C29A C24A -0.6(5) . . . . ?
C25A C24A C29A C28A 2.5(4) . . . . ?
C23A C24A C29A C28A -176.5(2) . . . . ?
N2A C21A C31A O3A 28.5(3) . . . . ?
C22A C21A C31A O3A -83.8(2) . . . . ?
N2A C21A C31A C32A -155.15(15) . . . . ?
C22A C21A C31A C32A 92.53(18) . . . . ?
C36A N4A C32A C33A 0.4(3) . . . . ?
C36A N4A C32A C31A -179.62(17) . . . . ?
O3A C31A C32A N4A -169.81(19) . . . . ?
C21A C31A C32A N4A 13.8(2) . . . . ?
O3A C31A C32A C33A 10.1(3) . . . . ?
C21A C31A C32A C33A -166.22(16) . . . . ?
N4A C32A C33A C34A -0.9(3) . . . . ?
C31A C32A C33A C34A 179.15(16) . . . . ?
C32A C33A C34A C35A 0.2(3) . . . . ?
C33A C34A C35A C36A 0.9(3) . . . . ?
C32A N4A C36A C35A 0.7(3) . . . . ?
C34A C35A C36A N4A -1.4(3) . . . . ?
N3A N2A C41A C42A 177.70(17) . . . . ?
C21A N2A C41A C42A -15.7(3) . . . . ?
N3A N2A C41A C46A -2.9(3) . . . . ?
C21A N2A C41A C46A 163.70(17) . . . . ?
N2A C41A C42A C43A 178.02(19) . . . . ?
C46A C41A C42A C43A -1.4(3) . . . . ?
C41A C42A C43A C44A 0.9(3) . . . . ?
C42A C43A C44A C45A 0.5(4) . . . . ?
C43A C44A C45A C46A -1.4(4) . . . . ?
C44A C45A C46A C41A 0.8(3) . . . . ?
C42A C41A C46A C45A 0.6(3) . . . . ?
N2A C41A C46A C45A -178.86(19) . . . . ?
C41B N2B N3B C23B -177.44(16) . . . . ?
C21B N2B N3B C23B -8.5(2) . . . . ?
C3B O1B C2B C1B 172.17(17) . . . . ?
C2B O1B C3B O2B -1.0(3) . . . . ?
C2B O1B C3B C4B 179.31(15) . . . . ?
C7B N1B C4B C5B -1.5(2) . . . . ?
C22B N1B C4B C5B -168.59(15) . . . . ?
C7B N1B C4B C3B 179.80(16) . . . . ?
C22B N1B C4B C3B 12.7(3) . . . . ?
O2B C3B C4B C5B -164.63(19) . . . . ?
O1B C3B C4B C5B 15.0(3) . . . . ?
O2B C3B C4B N1B 13.8(3) . . . . ?
O1B C3B C4B N1B -166.49(16) . . . . ?
N1B C4B C5B C6B 1.0(2) . . . . ?
C3B C4B C5B C6B 179.65(17) . . . . ?
C4B C5B C6B C11B 178.6(2) . . . . ?
C4B C5B C6B C7B -0.2(2) . . . . ?
C4B N1B C7B C8B -178.02(19) . . . . ?
C22B N1B C7B C8B -10.9(3) . . . . ?
C4B N1B C7B C6B 1.36(19) . . . . ?
C22B N1B C7B C6B 168.50(15) . . . . ?
C11B C6B C7B N1B -179.69(18) . . . . ?
C5B C6B C7B N1B -0.8(2) . . . . ?
C11B C6B C7B C8B -0.2(3) . . . . ?
C5B C6B C7B C8B 178.70(18) . . . . ?
N1B C7B C8B C9B 179.8(2) . . . . ?
C6B C7B C8B C9B 0.5(3) . . . . ?
C7B C8B C9B C10B -0.7(3) . . . . ?
C8B C9B C10B C11B 0.7(4) . . . . ?
C9B C10B C11B C6B -0.4(4) . . . . ?
C7B C6B C11B C10B 0.1(3) . . . . ?
C5B C6B C11B C10B -178.4(2) . . . . ?
N3B N2B C21B C31B -106.06(17) . . . . ?
C41B N2B C21B C31B 62.3(2) . . . . ?
N3B N2B C21B C22B 10.89(19) . . . . ?
C41B N2B C21B C22B 179.28(16) . . . . ?
C7B N1B C22B C23B 56.9(2) . . . . ?
C4B N1B C22B C23B -138.25(16) . . . . ?
C7B N1B C22B C21B -58.4(2) . . . . ?
C4B N1B C22B C21B 106.45(18) . . . . ?
N2B C21B C22B N1B 114.03(15) . . . . ?
C31B C21B C22B N1B -127.47(15) . . . . ?
N2B C21B C22B C23B -8.62(16) . . . . ?
C31B C21B C22B C23B 109.87(15) . . . . ?
N2B N3B C23B C24B -176.41(15) . . . . ?
N2B N3B C23B C22B 1.9(2) . . . . ?
N1B C22B C23B N3B -118.44(16) . . . . ?
C21B C22B C23B N3B 4.63(19) . . . . ?
N1B C22B C23B C24B 59.8(2) . . . . ?
C21B C22B C23B C24B -177.10(16) . . . . ?
N3B C23B C24B C25B -166.05(17) . . . . ?
C22B C23B C24B C25B 15.8(3) . . . . ?
N3B C23B C24B C29B 14.6(3) . . . . ?
C22B C23B C24B C29B -163.55(16) . . . . ?
C29B C24B C25B C26B 0.5(3) . . . . ?
C23B C24B C25B C26B -178.88(17) . . . . ?
C24B C25B C26B C27B 0.5(3) . . . . ?
C25B C26B C27B C28B -1.1(3) . . . . ?
C26B C27B C28B C29B 0.6(3) . . . . ?
C27B C28B C29B C24B 0.4(3) . . . . ?
C25B C24B C29B C28B -0.9(3) . . . . ?
C23B C24B C29B C28B 178.45(17) . . . . ?
N2B C21B C31B O3B 13.4(3) . . . . ?
C22B C21B C31B O3B -99.2(2) . . . . ?
N2B C21B C31B C32B -168.01(15) . . . . ?
C22B C21B C31B C32B 79.36(19) . . . . ?
C36B N4B C32B C33B -0.4(3) . . . . ?
C36B N4B C32B C31B 179.93(18) . . . . ?
O3B C31B C32B N4B 176.85(19) . . . . ?
C21B C31B C32B N4B -1.7(2) . . . . ?
O3B C31B C32B C33B -2.8(3) . . . . ?
C21B C31B C32B C33B 178.67(18) . . . . ?
N4B C32B C33B C34B 1.3(3) . . . . ?
C31B C32B C33B C34B -179.09(19) . . . . ?
C32B C33B C34B C35B -0.2(3) . . . . ?
C33B C34B C35B C36B -1.6(3) . . . . ?
C32B N4B C36B C35B -1.5(3) . . . . ?
C34B C35B C36B N4B 2.6(3) . . . . ?
N3B N2B C41B C42B -3.5(3) . . . . ?
C21B N2B C41B C42B -170.99(17) . . . . ?
N3B N2B C41B C46B 177.99(17) . . . . ?
C21B N2B C41B C46B 10.5(3) . . . . ?
N2B C41B C42B C43B -178.31(17) . . . . ?
C46B C41B C42B C43B 0.3(3) . . . . ?
C41B C42B C43B C44B -0.6(3) . . . . ?
C42B C43B C44B C45B 0.3(3) . . . . ?
C43B C44B C45B C46B 0.4(3) . . . . ?
C44B C45B C46B C41B -0.7(3) . . . . ?
N2B C41B C46B C45B 178.97(17) . . . . ?
C42B C41B C46B C45B 0.4(3) . . . . ?

_refine_diff_density_max         0.151
_refine_diff_density_min         -0.139
_refine_diff_density_rms         0.028


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: DCM, Hexane'
