# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_4a
_database_code_depnum_ccdc_archive 'CCDC 2296937'
loop_
_audit_author_name
_audit_author_address
'Chao-Guo Yan' 'Yangzhou University'
_audit_update_record             
;
2023-09-23 deposited with the CCDC.	2023-11-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C36 H29 N3 O5'
_chemical_formula_sum            'C36 H29 N3 O5'
_chemical_formula_weight         583.62

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

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

_cell_length_a                   13.0387(13)
_cell_length_b                   18.890(2)
_cell_length_c                   14.4657(15)
_cell_angle_alpha                90
_cell_angle_beta                 106.702(3)
_cell_angle_gamma                90
_cell_volume                     3412.6(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5993
_cell_measurement_theta_min      2.61
_cell_measurement_theta_max      23.77

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.136
_exptl_crystal_F_000             1224
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    0.077
_shelx_estimated_absorpt_T_min   0.982
_shelx_estimated_absorpt_T_max   0.986
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6846
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            31950
_diffrn_reflns_av_unetI/netI     0.0779
_diffrn_reflns_av_R_equivalents  0.0700
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.146
_diffrn_reflns_theta_max         26.000
_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             6686
_reflns_number_gt                3487
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0935P)²+1.4268P] 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         6686
_refine_ls_number_parameters     400
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1448
_refine_ls_R_factor_gt           0.0673
_refine_ls_wR_factor_ref         0.2039
_refine_ls_wR_factor_gt          0.1659
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_restrained_S_all      1.021
_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
C1 C 0.4294(3) 0.8856(2) 0.6225(2) 0.0604(10) Uani 1 1 d . . . . .
H1 H 0.4928 0.9007 0.6662 0.072 Uiso 1 1 calc R U . . .
C2 C 0.4272(3) 0.8686(2) 0.5290(3) 0.0725(12) Uani 1 1 d . . . . .
H2 H 0.4900 0.8720 0.5110 0.087 Uiso 1 1 calc R U . . .
C3 C 0.3352(3) 0.8468(2) 0.4620(2) 0.0638(10) Uani 1 1 d . . . . .
C4 C 0.3362(4) 0.8268(3) 0.3610(3) 0.1024(16) Uani 1 1 d . . . . .
H4A H 0.3218 0.7771 0.3510 0.154 Uiso 1 1 calc R U . . .
H4B H 0.4053 0.8373 0.3530 0.154 Uiso 1 1 calc R U . . .
H4C H 0.2823 0.8533 0.3148 0.154 Uiso 1 1 calc R U . . .
C5 C 0.2434(3) 0.84280(18) 0.4917(2) 0.0542(9) Uani 1 1 d . . . . .
H5 H 0.1796 0.8286 0.4478 0.065 Uiso 1 1 calc R U . . .
C6 C 0.2443(3) 0.85918(17) 0.5843(2) 0.0472(8) Uani 1 1 d . . . . .
H6 H 0.1815 0.8560 0.6024 0.057 Uiso 1 1 calc R U . . .
C7 C 0.3379(2) 0.88029(16) 0.6504(2) 0.0409(7) Uani 1 1 d . . . . .
C8 C 0.3856(2) 0.84615(16) 0.8194(2) 0.0373(7) Uani 1 1 d . . . . .
C9 C 0.3979(3) 0.77374(18) 0.7801(2) 0.0449(8) Uani 1 1 d . . . . .
C10 C 0.5111(3) 0.6990(2) 0.7239(3) 0.0878(14) Uani 1 1 d . . . . .
H10A H 0.5037 0.6601 0.7642 0.132 Uiso 1 1 calc R U . . .
H10B H 0.5817 0.6985 0.7158 0.132 Uiso 1 1 calc R U . . .
H10C H 0.4589 0.6947 0.6620 0.132 Uiso 1 1 calc R U . . .
C11 C 0.4082(2) 0.85777(15) 0.9171(2) 0.0374(7) Uani 1 1 d . . . . .
C12 C 0.4554(2) 0.80102(19) 0.9840(2) 0.0445(8) Uani 1 1 d . . . . .
C13 C 0.5283(3) 0.7712(2) 1.1492(2) 0.0730(11) Uani 1 1 d . . . . .
H13A H 0.4950 0.7258 1.1337 0.109 Uiso 1 1 calc R U . . .
H13B H 0.5227 0.7864 1.2109 0.109 Uiso 1 1 calc R U . . .
H13C H 0.6025 0.7679 1.1515 0.109 Uiso 1 1 calc R U . . .
C14 C 0.3584(2) 1.02323(16) 1.0270(2) 0.0369(7) Uani 1 1 d . . . . .
C15 C 0.3580(2) 1.07157(18) 1.0984(2) 0.0445(8) Uani 1 1 d . . . . .
H15 H 0.3880 1.0608 1.1633 0.053 Uiso 1 1 calc R U . . .
C16 C 0.3115(3) 1.13621(18) 1.0697(2) 0.0510(9) Uani 1 1 d . . . . .
H16 H 0.3104 1.1700 1.1162 0.061 Uiso 1 1 calc R U . . .
C17 C 0.2664(3) 1.15229(18) 0.9731(2) 0.0528(9) Uani 1 1 d . . . . .
H17 H 0.2356 1.1966 0.9564 0.063 Uiso 1 1 calc R U . . .
C18 C 0.2659(3) 1.10469(17) 0.9015(2) 0.0481(8) Uani 1 1 d . . . . .
H18 H 0.2348 1.1162 0.8370 0.058 Uiso 1 1 calc R U . . .
C19 C 0.3133(2) 1.03808(16) 0.92785(19) 0.0371(7) Uani 1 1 d . . . . .
C20 C 0.3308(2) 0.97656(15) 0.87700(19) 0.0352(7) Uani 1 1 d . . . . .
C21 C 0.3821(2) 0.92770(16) 0.94348(19) 0.0355(7) Uani 1 1 d . . . . .
C22 C 0.3098(3) 1.0517(2) 0.4706(3) 0.0694(11) Uani 1 1 d . . . . .
H22 H 0.3355 1.0142 0.5124 0.083 Uiso 1 1 calc R U . . .
C23 C 0.2975(3) 1.0438(3) 0.3727(3) 0.0837(13) Uani 1 1 d . . . . .
H23 H 0.3150 1.0009 0.3494 0.100 Uiso 1 1 calc R U . . .
C24 C 0.2604(4) 1.0973(4) 0.3111(3) 0.0940(16) Uani 1 1 d . . . . .
H24 H 0.2533 1.0916 0.2457 0.113 Uiso 1 1 calc R U . . .
C25 C 0.2335(4) 1.1596(3) 0.3443(3) 0.0987(16) Uani 1 1 d . . . . .
H25 H 0.2071 1.1965 0.3014 0.118 Uiso 1 1 calc R U . . .
C26 C 0.2453(3) 1.1686(3) 0.4425(3) 0.0838(13) Uani 1 1 d . . . . .
H26 H 0.2266 1.2114 0.4649 0.101 Uiso 1 1 calc R U . . .
C27 C 0.2845(3) 1.1145(2) 0.5062(2) 0.0549(9) Uani 1 1 d . . . . .
C28 C 0.3031(3) 1.12624(18) 0.6136(2) 0.0602(10) Uani 1 1 d . . . . .
H28A H 0.3766 1.1413 0.6419 0.072 Uiso 1 1 calc R U . . .
H28B H 0.2569 1.1642 0.6226 0.072 Uiso 1 1 calc R U . . .
C29 C 0.1804(2) 1.03797(17) 0.6581(2) 0.0434(8) Uani 1 1 d . . . . .
C30 C 0.0826(3) 1.0647(2) 0.6048(2) 0.0606(10) Uani 1 1 d . . . . .
H30 H 0.0778 1.1047 0.5662 0.073 Uiso 1 1 calc R U . . .
C31 C -0.0070(3) 1.0293(3) 0.6116(3) 0.0767(12) Uani 1 1 d . . . . .
H31 H -0.0740 1.0455 0.5758 0.092 Uiso 1 1 calc R U . . .
C32 C -0.0012(3) 0.9708(2) 0.6692(3) 0.0741(12) Uani 1 1 d . . . . .
H32 H -0.0637 0.9482 0.6717 0.089 Uiso 1 1 calc R U . . .
C33 C 0.0977(3) 0.9452(2) 0.7238(2) 0.0574(9) Uani 1 1 d . . . . .
H33 H 0.1024 0.9061 0.7639 0.069 Uiso 1 1 calc R U . . .
C34 C 0.1885(2) 0.97947(16) 0.7170(2) 0.0391(7) Uani 1 1 d . . . . .
C35 C 0.3051(2) 0.96604(15) 0.77066(19) 0.0378(7) Uani 1 1 d . . . . .
C36 C 0.3606(3) 1.02552(16) 0.7265(2) 0.0420(8) Uani 1 1 d . . . . .
N1 N 0.34291(19) 0.89537(13) 0.75047(16) 0.0404(6) Uani 1 1 d . . . . .
N2 N 0.39902(19) 0.95573(13) 1.03451(16) 0.0395(6) Uani 1 1 d . . . . .
H2A H 0.4301 0.9343 1.0877 0.047 Uiso 1 1 calc R U . . .
N3 N 0.2833(2) 1.06415(14) 0.66437(17) 0.0452(7) Uani 1 1 d . . . . .
O1 O 0.32534(19) 0.73262(12) 0.75668(16) 0.0590(6) Uani 1 1 d . . . . .
O2 O 0.49475(18) 0.76503(12) 0.76875(15) 0.0585(6) Uani 1 1 d . . . . .
O3 O 0.4747(2) 0.74202(13) 0.96269(16) 0.0663(7) Uani 1 1 d . . . . .
O4 O 0.47563(18) 0.82176(12) 1.07645(14) 0.0568(6) Uani 1 1 d . . . . .
O5 O 0.45633(18) 1.03634(12) 0.74667(15) 0.0559(6) 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
C1 C7 1.369(4) . ?
C1 C2 1.382(5) . ?
C1 H1 0.9300 . ?
C2 C3 1.371(5) . ?
C2 H2 0.9300 . ?
C3 C5 1.385(5) . ?
C3 C4 1.514(5) . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C5 C6 1.371(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.376(4) . ?
C6 H6 0.9300 . ?
C7 N1 1.458(3) . ?
C8 N1 1.360(4) . ?
C8 C11 1.375(4) . ?
C8 C9 1.508(4) . ?
C9 O1 1.195(4) . ?
C9 O2 1.330(4) . ?
C10 O2 1.449(4) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 C21 1.443(4) . ?
C11 C12 1.456(4) . ?
C12 O3 1.202(4) . ?
C12 O4 1.345(4) . ?
C13 O4 1.441(4) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 N2 1.373(4) . ?
C14 C15 1.380(4) . ?
C14 C19 1.413(4) . ?
C15 C16 1.373(5) . ?
C15 H15 0.9300 . ?
C16 C17 1.385(4) . ?
C16 H16 0.9300 . ?
C17 C18 1.370(4) . ?
C17 H17 0.9300 . ?
C18 C19 1.406(4) . ?
C18 H18 0.9300 . ?
C19 C20 1.428(4) . ?
C20 C21 1.362(4) . ?
C20 C35 1.491(4) . ?
C21 N2 1.377(3) . ?
C22 C27 1.370(5) . ?
C22 C23 1.387(5) . ?
C22 H22 0.9300 . ?
C23 C24 1.343(6) . ?
C23 H23 0.9300 . ?
C24 C25 1.355(7) . ?
C24 H24 0.9300 . ?
C25 C26 1.395(6) . ?
C25 H25 0.9300 . ?
C26 C27 1.373(5) . ?
C26 H26 0.9300 . ?
C27 C28 1.519(5) . ?
C28 N3 1.446(4) . ?
C28 H28A 0.9700 . ?
C28 H28B 0.9700 . ?
C29 C34 1.380(4) . ?
C29 C30 1.382(4) . ?
C29 N3 1.408(4) . ?
C30 C31 1.375(6) . ?
C30 H30 0.9300 . ?
C31 C32 1.373(6) . ?
C31 H31 0.9300 . ?
C32 C33 1.391(5) . ?
C32 H32 0.9300 . ?
C33 C34 1.377(4) . ?
C33 H33 0.9300 . ?
C34 C35 1.517(4) . ?
C35 N1 1.481(4) . ?
C35 C36 1.568(4) . ?
C36 O5 1.215(3) . ?
C36 N3 1.354(4) . ?
N2 H2A 0.8600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 C1 C2 119.8(3) . . ?
C7 C1 H1 120.1 . . ?
C2 C1 H1 120.1 . . ?
C3 C2 C1 122.0(3) . . ?
C3 C2 H2 119.0 . . ?
C1 C2 H2 119.0 . . ?
C2 C3 C5 117.1(3) . . ?
C2 C3 C4 120.6(4) . . ?
C5 C3 C4 122.3(4) . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C6 C5 C3 121.7(3) . . ?
C6 C5 H5 119.2 . . ?
C3 C5 H5 119.2 . . ?
C5 C6 C7 120.1(3) . . ?
C5 C6 H6 119.9 . . ?
C7 C6 H6 119.9 . . ?
C1 C7 C6 119.3(3) . . ?
C1 C7 N1 119.0(3) . . ?
C6 C7 N1 121.7(3) . . ?
N1 C8 C11 124.5(3) . . ?
N1 C8 C9 114.1(2) . . ?
C11 C8 C9 121.2(3) . . ?
O1 C9 O2 125.9(3) . . ?
O1 C9 C8 122.3(3) . . ?
O2 C9 C8 111.5(3) . . ?
O2 C10 H10A 109.5 . . ?
O2 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
O2 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C8 C11 C21 114.9(3) . . ?
C8 C11 C12 119.3(3) . . ?
C21 C11 C12 125.8(3) . . ?
O3 C12 O4 121.9(3) . . ?
O3 C12 C11 126.3(3) . . ?
O4 C12 C11 111.8(3) . . ?
O4 C13 H13A 109.5 . . ?
O4 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
O4 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N2 C14 C15 129.8(3) . . ?
N2 C14 C19 107.6(2) . . ?
C15 C14 C19 122.6(3) . . ?
C16 C15 C14 117.3(3) . . ?
C16 C15 H15 121.4 . . ?
C14 C15 H15 121.4 . . ?
C15 C16 C17 121.5(3) . . ?
C15 C16 H16 119.2 . . ?
C17 C16 H16 119.2 . . ?
C18 C17 C16 121.8(3) . . ?
C18 C17 H17 119.1 . . ?
C16 C17 H17 119.1 . . ?
C17 C18 C19 118.5(3) . . ?
C17 C18 H18 120.8 . . ?
C19 C18 H18 120.8 . . ?
C18 C19 C14 118.3(3) . . ?
C18 C19 C20 135.4(3) . . ?
C14 C19 C20 106.3(3) . . ?
C21 C20 C19 107.9(2) . . ?
C21 C20 C35 123.9(3) . . ?
C19 C20 C35 128.2(3) . . ?
C20 C21 N2 109.0(3) . . ?
C20 C21 C11 122.6(2) . . ?
N2 C21 C11 128.3(2) . . ?
C27 C22 C23 120.5(4) . . ?
C27 C22 H22 119.7 . . ?
C23 C22 H22 119.7 . . ?
C24 C23 C22 120.6(5) . . ?
C24 C23 H23 119.7 . . ?
C22 C23 H23 119.7 . . ?
C23 C24 C25 120.0(4) . . ?
C23 C24 H24 120.0 . . ?
C25 C24 H24 120.0 . . ?
C24 C25 C26 120.2(4) . . ?
C24 C25 H25 119.9 . . ?
C26 C25 H25 119.9 . . ?
C27 C26 C25 120.3(5) . . ?
C27 C26 H26 119.9 . . ?
C25 C26 H26 119.9 . . ?
C22 C27 C26 118.4(4) . . ?
C22 C27 C28 121.7(3) . . ?
C26 C27 C28 119.9(4) . . ?
N3 C28 C27 113.7(3) . . ?
N3 C28 H28A 108.8 . . ?
C27 C28 H28A 108.8 . . ?
N3 C28 H28B 108.8 . . ?
C27 C28 H28B 108.8 . . ?
H28A C28 H28B 107.7 . . ?
C34 C29 C30 122.1(3) . . ?
C34 C29 N3 109.8(3) . . ?
C30 C29 N3 128.0(3) . . ?
C31 C30 C29 116.7(4) . . ?
C31 C30 H30 121.7 . . ?
C29 C30 H30 121.7 . . ?
C32 C31 C30 122.4(4) . . ?
C32 C31 H31 118.8 . . ?
C30 C31 H31 118.8 . . ?
C31 C32 C33 120.3(4) . . ?
C31 C32 H32 119.8 . . ?
C33 C32 H32 119.8 . . ?
C34 C33 C32 118.1(4) . . ?
C34 C33 H33 120.9 . . ?
C32 C33 H33 120.9 . . ?
C33 C34 C29 120.4(3) . . ?
C33 C34 C35 129.8(3) . . ?
C29 C34 C35 109.7(3) . . ?
N1 C35 C20 109.6(2) . . ?
N1 C35 C34 113.0(2) . . ?
C20 C35 C34 113.7(2) . . ?
N1 C35 C36 110.3(2) . . ?
C20 C35 C36 109.4(2) . . ?
C34 C35 C36 100.6(2) . . ?
O5 C36 N3 125.9(3) . . ?
O5 C36 C35 125.8(3) . . ?
N3 C36 C35 108.3(3) . . ?
C8 N1 C7 119.1(2) . . ?
C8 N1 C35 124.1(2) . . ?
C7 N1 C35 116.7(2) . . ?
C14 N2 C21 109.2(2) . . ?
C14 N2 H2A 125.4 . . ?
C21 N2 H2A 125.4 . . ?
C36 N3 C29 111.5(3) . . ?
C36 N3 C28 124.5(3) . . ?
C29 N3 C28 124.0(3) . . ?
C9 O2 C10 115.4(3) . . ?
C12 O4 C13 116.7(3) . . ?

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
N2 H2A O4 0.86 2.23 2.724(3) 116.8 .
N2 H2A O5 0.86 2.49 3.189(3) 138.8 3_677

_refine_diff_density_max         0.224
_refine_diff_density_min         -0.209
_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_4k
_database_code_depnum_ccdc_archive 'CCDC 2297153'
loop_
_audit_author_name
_audit_author_address
'Chao-Guo Yan' 'Yangzhou University'
_audit_update_record             
;
2023-09-25 deposited with the CCDC.	2023-11-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C36 H28 Cl N3 O5'
_chemical_formula_sum            'C36 H28 Cl N3 O5'
_chemical_formula_weight         618.06

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'
Cl Cl 0.1484 0.1585 '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                   11.4127(17)
_cell_length_b                   11.889(2)
_cell_length_c                   14.951(2)
_cell_angle_alpha                67.152(5)
_cell_angle_beta                 72.453(4)
_cell_angle_gamma                70.704(5)
_cell_volume                     1729.2(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4335
_cell_measurement_theta_min      2.37
_cell_measurement_theta_max      22.30

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.187
_exptl_crystal_F_000             644
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    0.154
_shelx_estimated_absorpt_T_min   0.964
_shelx_estimated_absorpt_T_max   0.973
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6873
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            24869
_diffrn_reflns_av_unetI/netI     0.1134
_diffrn_reflns_av_R_equivalents  0.0785
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.205
_diffrn_reflns_theta_max         25.998
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             6787
_reflns_number_gt                3251
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0746P)²+0.1780P] 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         6787
_refine_ls_number_parameters     409
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1614
_refine_ls_R_factor_gt           0.0656
_refine_ls_wR_factor_ref         0.1679
_refine_ls_wR_factor_gt          0.1348
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_restrained_S_all      1.009
_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
C1 C 0.7164(3) 0.7099(3) 0.5455(3) 0.0638(10) Uani 1 1 d . . . . .
H1 H 0.7500 0.7587 0.5623 0.077 Uiso 1 1 calc R U . . .
C2 C 0.7242(4) 0.7303(4) 0.4466(3) 0.0753(11) Uani 1 1 d . . . . .
H2A H 0.7606 0.7936 0.3983 0.090 Uiso 1 1 calc R U . . .
C3 C 0.6800(4) 0.6597(5) 0.4199(3) 0.0874(14) Uani 1 1 d . . . . .
H3 H 0.6859 0.6734 0.3533 0.105 Uiso 1 1 calc R U . . .
C4 C 0.6265(4) 0.5677(5) 0.4907(4) 0.1019(16) Uani 1 1 d . . . . .
H4 H 0.5967 0.5173 0.4726 0.122 Uiso 1 1 calc R U . . .
C5 C 0.6161(3) 0.5486(4) 0.5909(3) 0.0764(12) Uani 1 1 d . . . . .
H5 H 0.5782 0.4862 0.6390 0.092 Uiso 1 1 calc R U . . .
C6 C 0.6608(3) 0.6202(3) 0.6193(2) 0.0481(8) Uani 1 1 d . . . . .
C7 C 0.6484(3) 0.5951(3) 0.7286(2) 0.0522(9) Uani 1 1 d . . . . .
H7A H 0.5594 0.6178 0.7581 0.063 Uiso 1 1 calc R U . . .
H7B H 0.6799 0.5056 0.7598 0.063 Uiso 1 1 calc R U . . .
C8 C 0.6787(3) 0.7936(3) 0.73633(19) 0.0378(7) Uani 1 1 d . . . . .
C9 C 0.5672(3) 0.8786(3) 0.7132(2) 0.0515(9) Uani 1 1 d . . . . .
H9 H 0.5037 0.8533 0.7045 0.062 Uiso 1 1 calc R U . . .
C10 C 0.5531(3) 1.0022(3) 0.7036(2) 0.0590(10) Uani 1 1 d . . . . .
H10 H 0.4784 1.0605 0.6883 0.071 Uiso 1 1 calc R U . . .
C11 C 0.6463(3) 1.0431(3) 0.7159(2) 0.0524(9) Uani 1 1 d . . . . .
C12 C 0.6283(4) 1.1800(3) 0.7027(3) 0.0860(12) Uani 1 1 d . . . . .
H12A H 0.6873 1.1874 0.7330 0.129 Uiso 1 1 calc R U . . .
H12B H 0.5434 1.2128 0.7333 0.129 Uiso 1 1 calc R U . . .
H12C H 0.6427 1.2268 0.6333 0.129 Uiso 1 1 calc R U . . .
C13 C 0.7565(3) 0.9554(3) 0.7417(2) 0.0455(8) Uani 1 1 d . . . . .
H13 H 0.8193 0.9800 0.7521 0.055 Uiso 1 1 calc R U . . .
C14 C 0.7714(2) 0.8311(3) 0.75190(19) 0.0353(7) Uani 1 1 d . . . . .
C15 C 0.8765(2) 0.7163(3) 0.78537(19) 0.0335(7) Uani 1 1 d . . . . .
C16 C 0.8289(3) 0.6099(3) 0.7801(2) 0.0394(8) Uani 1 1 d . . . . .
C17 C 0.8564(3) 0.6371(3) 1.0555(2) 0.0368(7) Uani 1 1 d . . . . .
C18 C 0.7946(3) 0.6068(3) 1.1543(2) 0.0476(8) Uani 1 1 d . . . . .
H18 H 0.8362 0.5894 1.2046 0.057 Uiso 1 1 calc R U . . .
C19 C 0.6702(3) 0.6034(3) 1.1747(2) 0.0527(9) Uani 1 1 d . . . . .
H19 H 0.6269 0.5825 1.2402 0.063 Uiso 1 1 calc R U . . .
C20 C 0.6076(3) 0.6308(3) 1.0993(2) 0.0546(9) Uani 1 1 d . . . . .
H20 H 0.5228 0.6287 1.1156 0.066 Uiso 1 1 calc R U . . .
C21 C 0.6674(3) 0.6609(3) 1.0011(2) 0.0446(8) Uani 1 1 d . . . . .
H21 H 0.6242 0.6795 0.9515 0.054 Uiso 1 1 calc R U . . .
C22 C 0.7957(3) 0.6628(3) 0.97818(19) 0.0346(7) Uani 1 1 d . . . . .
C23 C 0.8890(2) 0.6880(2) 0.88892(19) 0.0332(7) Uani 1 1 d . . . . .
C24 C 0.9987(3) 0.6775(2) 0.9139(2) 0.0345(7) Uani 1 1 d . . . . .
C25 C 0.9770(3) 0.8426(3) 0.5462(2) 0.0486(8) Uani 1 1 d . . . . .
H25 H 0.9453 0.9161 0.5630 0.058 Uiso 1 1 calc R U . . .
C26 C 0.9902(3) 0.8479(4) 0.4497(2) 0.0626(10) Uani 1 1 d . . . . .
H26 H 0.9677 0.9246 0.4013 0.075 Uiso 1 1 calc R U . . .
C27 C 1.0370(3) 0.7382(4) 0.4261(2) 0.0607(10) Uani 1 1 d . . . . .
C28 C 1.0687(3) 0.6244(4) 0.4959(3) 0.0605(10) Uani 1 1 d . . . . .
H28 H 1.0989 0.5510 0.4790 0.073 Uiso 1 1 calc R U . . .
C29 C 1.0553(3) 0.6197(3) 0.5919(2) 0.0520(9) Uani 1 1 d . . . . .
H29 H 1.0765 0.5425 0.6401 0.062 Uiso 1 1 calc R U . . .
C30 C 1.0104(3) 0.7291(3) 0.6173(2) 0.0387(7) Uani 1 1 d . . . . .
C31 C 1.1068(3) 0.7188(3) 0.7463(2) 0.0364(7) Uani 1 1 d . . . . .
C32 C 1.2189(3) 0.7393(4) 0.6620(2) 0.0454(8) Uani 1 1 d . . . . .
C33 C 1.3251(4) 0.8918(4) 0.5467(3) 0.0968(14) Uani 1 1 d . . . . .
H33A H 1.4026 0.8377 0.5669 0.145 Uiso 1 1 calc R U . . .
H33B H 1.3251 0.9778 0.5325 0.145 Uiso 1 1 calc R U . . .
H33C H 1.3181 0.8807 0.4885 0.145 Uiso 1 1 calc R U . . .
C34 C 1.1125(2) 0.6980(3) 0.8410(2) 0.0367(7) Uani 1 1 d . . . . .
C35 C 1.2300(3) 0.6949(3) 0.8616(2) 0.0434(8) Uani 1 1 d . . . . .
C36 C 1.3357(3) 0.6579(4) 0.9889(3) 0.0779(12) Uani 1 1 d . . . . .
H36A H 1.3989 0.5848 0.9786 0.117 Uiso 1 1 calc R U . . .
H36B H 1.3166 0.6506 1.0577 0.117 Uiso 1 1 calc R U . . .
H36C H 1.3670 0.7317 0.9500 0.117 Uiso 1 1 calc R U . . .
Cl1 Cl 1.05485(12) 0.74413(13) 0.30455(7) 0.1087(5) Uani 1 1 d . . . . .
N1 N 0.7160(2) 0.6632(2) 0.74943(17) 0.0419(6) Uani 1 1 d . . . . .
N2 N 0.9789(2) 0.6466(2) 1.01516(16) 0.0402(6) Uani 1 1 d . . . . .
H2 H 1.0345 0.6350 1.0479 0.048 Uiso 1 1 calc R U . . .
N3 N 1.0019(2) 0.7221(2) 0.71765(15) 0.0372(6) Uani 1 1 d . . . . .
O1 O 0.8832(2) 0.4983(2) 0.80066(15) 0.0513(6) Uani 1 1 d . . . . .
O2 O 1.2922(2) 0.6588(2) 0.63040(16) 0.0647(7) Uani 1 1 d . . . . .
O3 O 1.21875(19) 0.8606(2) 0.62562(15) 0.0595(6) Uani 1 1 d . . . . .
O4 O 1.3256(2) 0.7134(2) 0.80162(17) 0.0651(7) Uani 1 1 d . . . . .
O5 O 1.22239(19) 0.6677(2) 0.95960(15) 0.0579(6) 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
C1 C6 1.368(4) . ?
C1 C2 1.382(5) . ?
C1 H1 0.9300 . ?
C2 C3 1.334(5) . ?
C2 H2A 0.9300 . ?
C3 C4 1.357(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.399(6) . ?
C4 H4 0.9300 . ?
C5 C6 1.364(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.512(4) . ?
C7 N1 1.449(4) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.380(4) . ?
C8 C14 1.383(4) . ?
C8 N1 1.415(4) . ?
C9 C10 1.379(4) . ?
C9 H9 0.9300 . ?
C10 C11 1.388(4) . ?
C10 H10 0.9300 . ?
C11 C13 1.390(4) . ?
C11 C12 1.512(4) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 C14 1.383(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.517(4) . ?
C15 N3 1.489(3) . ?
C15 C23 1.493(4) . ?
C15 C16 1.568(4) . ?
C16 O1 1.222(3) . ?
C16 N1 1.365(4) . ?
C17 N2 1.369(3) . ?
C17 C18 1.391(4) . ?
C17 C22 1.405(4) . ?
C18 C19 1.370(4) . ?
C18 H18 0.9300 . ?
C19 C20 1.392(4) . ?
C19 H19 0.9300 . ?
C20 C21 1.378(4) . ?
C20 H20 0.9300 . ?
C21 C22 1.406(4) . ?
C21 H21 0.9300 . ?
C22 C23 1.431(4) . ?
C23 C24 1.366(4) . ?
C24 N2 1.376(3) . ?
C24 C34 1.443(4) . ?
C25 C30 1.374(4) . ?
C25 C26 1.384(4) . ?
C25 H25 0.9300 . ?
C26 C27 1.376(5) . ?
C26 H26 0.9300 . ?
C27 C28 1.364(5) . ?
C27 Cl1 1.742(3) . ?
C28 C29 1.378(4) . ?
C28 H28 0.9300 . ?
C29 C30 1.387(4) . ?
C29 H29 0.9300 . ?
C30 N3 1.445(3) . ?
C31 C34 1.358(4) . ?
C31 N3 1.372(3) . ?
C31 C32 1.510(4) . ?
C32 O2 1.192(4) . ?
C32 O3 1.329(4) . ?
C33 O3 1.448(4) . ?
C33 H33A 0.9600 . ?
C33 H33B 0.9600 . ?
C33 H33C 0.9600 . ?
C34 C35 1.450(4) . ?
C35 O4 1.207(3) . ?
C35 O5 1.353(3) . ?
C36 O5 1.442(3) . ?
C36 H36A 0.9600 . ?
C36 H36B 0.9600 . ?
C36 H36C 0.9600 . ?
N2 H2 0.8600 . ?

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
C6 C1 C2 121.9(3) . . ?
C6 C1 H1 119.0 . . ?
C2 C1 H1 119.0 . . ?
C3 C2 C1 120.5(4) . . ?
C3 C2 H2A 119.7 . . ?
C1 C2 H2A 119.7 . . ?
C2 C3 C4 119.5(4) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 H3 120.2 . . ?
C3 C4 C5 120.1(4) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C6 C5 C4 121.0(4) . . ?
C6 C5 H5 119.5 . . ?
C4 C5 H5 119.5 . . ?
C5 C6 C1 116.9(3) . . ?
C5 C6 C7 119.0(3) . . ?
C1 C6 C7 124.1(3) . . ?
N1 C7 C6 113.9(2) . . ?
N1 C7 H7A 108.8 . . ?
C6 C7 H7A 108.8 . . ?
N1 C7 H7B 108.8 . . ?
C6 C7 H7B 108.8 . . ?
H7A C7 H7B 107.7 . . ?
C9 C8 C14 120.8(3) . . ?
C9 C8 N1 128.5(3) . . ?
C14 C8 N1 110.6(2) . . ?
C10 C9 C8 117.8(3) . . ?
C10 C9 H9 121.1 . . ?
C8 C9 H9 121.1 . . ?
C9 C10 C11 122.6(3) . . ?
C9 C10 H10 118.7 . . ?
C11 C10 H10 118.7 . . ?
C10 C11 C13 118.8(3) . . ?
C10 C11 C12 121.0(3) . . ?
C13 C11 C12 120.3(3) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C14 C13 C11 119.1(3) . . ?
C14 C13 H13 120.4 . . ?
C11 C13 H13 120.4 . . ?
C13 C14 C8 120.9(3) . . ?
C13 C14 C15 130.0(3) . . ?
C8 C14 C15 109.0(3) . . ?
N3 C15 C23 109.5(2) . . ?
N3 C15 C14 113.4(2) . . ?
C23 C15 C14 113.5(2) . . ?
N3 C15 C16 109.2(2) . . ?
C23 C15 C16 109.4(2) . . ?
C14 C15 C16 101.3(2) . . ?
O1 C16 N1 125.9(3) . . ?
O1 C16 C15 125.8(3) . . ?
N1 C16 C15 108.3(3) . . ?
N2 C17 C18 129.4(3) . . ?
N2 C17 C22 108.3(2) . . ?
C18 C17 C22 122.3(3) . . ?
C19 C18 C17 117.6(3) . . ?
C19 C18 H18 121.2 . . ?
C17 C18 H18 121.2 . . ?
C18 C19 C20 121.2(3) . . ?
C18 C19 H19 119.4 . . ?
C20 C19 H19 119.4 . . ?
C21 C20 C19 121.9(3) . . ?
C21 C20 H20 119.0 . . ?
C19 C20 H20 119.0 . . ?
C20 C21 C22 118.1(3) . . ?
C20 C21 H21 121.0 . . ?
C22 C21 H21 121.0 . . ?
C17 C22 C21 119.0(2) . . ?
C17 C22 C23 105.9(2) . . ?
C21 C22 C23 135.1(3) . . ?
C24 C23 C22 107.9(2) . . ?
C24 C23 C15 123.7(2) . . ?
C22 C23 C15 128.3(2) . . ?
C23 C24 N2 108.8(2) . . ?
C23 C24 C34 122.5(2) . . ?
N2 C24 C34 128.8(2) . . ?
C30 C25 C26 120.2(3) . . ?
C30 C25 H25 119.9 . . ?
C26 C25 H25 119.9 . . ?
C27 C26 C25 119.2(3) . . ?
C27 C26 H26 120.4 . . ?
C25 C26 H26 120.4 . . ?
C28 C27 C26 121.5(3) . . ?
C28 C27 Cl1 119.0(3) . . ?
C26 C27 Cl1 119.5(3) . . ?
C27 C28 C29 119.1(3) . . ?
C27 C28 H28 120.5 . . ?
C29 C28 H28 120.5 . . ?
C28 C29 C30 120.6(3) . . ?
C28 C29 H29 119.7 . . ?
C30 C29 H29 119.7 . . ?
C25 C30 C29 119.5(3) . . ?
C25 C30 N3 121.1(3) . . ?
C29 C30 N3 119.4(3) . . ?
C34 C31 N3 124.4(2) . . ?
C34 C31 C32 122.0(2) . . ?
N3 C31 C32 113.7(2) . . ?
O2 C32 O3 125.7(3) . . ?
O2 C32 C31 124.5(3) . . ?
O3 C32 C31 109.7(3) . . ?
O3 C33 H33A 109.5 . . ?
O3 C33 H33B 109.5 . . ?
H33A C33 H33B 109.5 . . ?
O3 C33 H33C 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
C31 C34 C24 115.7(2) . . ?
C31 C34 C35 118.9(3) . . ?
C24 C34 C35 125.5(3) . . ?
O4 C35 O5 121.8(3) . . ?
O4 C35 C34 126.4(3) . . ?
O5 C35 C34 111.8(3) . . ?
O5 C36 H36A 109.5 . . ?
O5 C36 H36B 109.5 . . ?
H36A C36 H36B 109.5 . . ?
O5 C36 H36C 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
C16 N1 C8 110.7(2) . . ?
C16 N1 C7 123.9(3) . . ?
C8 N1 C7 125.4(3) . . ?
C17 N2 C24 109.1(2) . . ?
C17 N2 H2 125.4 . . ?
C24 N2 H2 125.4 . . ?
C31 N3 C30 120.0(2) . . ?
C31 N3 C15 123.6(2) . . ?
C30 N3 C15 116.4(2) . . ?
C32 O3 C33 115.1(3) . . ?
C35 O5 C36 116.5(2) . . ?

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
N2 H2 O1 0.86 2.46 3.188(3) 143.4 2_767
N2 H2 O5 0.86 2.22 2.717(3) 116.6 .

_refine_diff_density_max         0.212
_refine_diff_density_min         -0.209
_refine_diff_density_rms         0.044



#=============================================================
####################################################################### 
# 
# 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_5b
_database_code_depnum_ccdc_archive 'CCDC 2296940'
loop_
_audit_author_name
_audit_author_address
'Chao-Guo Yan' 'Yangzhou University'
_audit_update_record             
;
2023-09-23 deposited with the CCDC.	2023-11-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C36 H31 N3 O5'
_chemical_formula_sum            'C36 H31 N3 O5'
_chemical_formula_weight         585.64

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/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                   19.3769(10)
_cell_length_b                   9.5886(5)
_cell_length_c                   18.2820(10)
_cell_angle_alpha                90
_cell_angle_beta                 113.8977(16)
_cell_angle_gamma                90
_cell_volume                     3105.5(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    7516
_cell_measurement_theta_min      2.23
_cell_measurement_theta_max      22.97

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.253
_exptl_crystal_F_000             1232
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    0.084
_shelx_estimated_absorpt_T_min   0.978
_shelx_estimated_absorpt_T_max   0.985
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7055
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            28436
_diffrn_reflns_av_unetI/netI     0.0540
_diffrn_reflns_av_R_equivalents  0.0552
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.234
_diffrn_reflns_theta_max         25.997
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             6104
_reflns_number_gt                3605
_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0538P)²+0.7753P] 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         6104
_refine_ls_number_parameters     446
_refine_ls_number_restraints     304
_refine_ls_R_factor_all          0.1141
_refine_ls_R_factor_gt           0.0551
_refine_ls_wR_factor_ref         0.1347
_refine_ls_wR_factor_gt          0.1126
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.068
_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
C1 C 0.2599(3) 0.4813(17) 0.4286(6) 0.0734(13) Uani 0.490(9) 1 d D U P A 1
H1 H 0.2338 0.5215 0.3786 0.088 Uiso 0.490(9) 1 calc R U P A 1
C2 C 0.2223(4) 0.3980(9) 0.4627(5) 0.0841(12) Uani 0.490(9) 1 d D U P A 1
H2 H 0.1712 0.3787 0.4349 0.101 Uiso 0.490(9) 1 calc R U P A 1
C3 C 0.2618(5) 0.3442(8) 0.5384(5) 0.0878(13) Uani 0.490(9) 1 d D U P A 1
H3 H 0.2370 0.2872 0.5612 0.105 Uiso 0.490(9) 1 calc R U P A 1
C4 C 0.3375(5) 0.3736(8) 0.5809(4) 0.0933(14) Uani 0.490(9) 1 d D U P A 1
H4 H 0.3632 0.3372 0.6320 0.112 Uiso 0.490(9) 1 calc R U P A 1
C5 C 0.3751(4) 0.4575(10) 0.5471(3) 0.0856(14) Uani 0.490(9) 1 d D U P A 1
H5 H 0.4254 0.4819 0.5758 0.103 Uiso 0.490(9) 1 calc R U P A 1
C1' C 0.2603(3) 0.4946(17) 0.4158(6) 0.0731(12) Uani 0.510(9) 1 d D U P A 2
H1' H 0.2453 0.5369 0.3659 0.088 Uiso 0.510(9) 1 calc R U P A 2
C2' C 0.2064(3) 0.4241(8) 0.4342(5) 0.0835(13) Uani 0.510(9) 1 d D U P A 2
H2' H 0.1560 0.4232 0.3982 0.100 Uiso 0.510(9) 1 calc R U P A 2
C3' C 0.2290(5) 0.3552(7) 0.5068(5) 0.0894(13) Uani 0.510(9) 1 d D U P A 2
H3' H 0.1938 0.3066 0.5196 0.107 Uiso 0.510(9) 1 calc R U P A 2
C4' C 0.3035(5) 0.3589(9) 0.5599(4) 0.0916(13) Uani 0.510(9) 1 d D U P A 2
H4' H 0.3187 0.3133 0.6089 0.110 Uiso 0.510(9) 1 calc R U P A 2
C5' C 0.3559(4) 0.4303(10) 0.5406(4) 0.0861(13) Uani 0.510(9) 1 d D U P A 2
H5' H 0.4063 0.4292 0.5764 0.103 Uiso 0.510(9) 1 calc R U P A 2
C6 C 0.33559(14) 0.5039(2) 0.46911(13) 0.0664(6) Uani 1 1 d D U . . .
C7 C 0.38823(14) 0.5838(3) 0.44284(13) 0.0693(7) Uani 1 1 d . U . . .
H7A H 0.4138 0.6538 0.4830 0.083 Uiso 1 1 calc R U . . .
H7B H 0.4264 0.5200 0.4411 0.083 Uiso 1 1 calc R U . . .
C8 C 0.35368(10) 0.5977(2) 0.29715(12) 0.0431(5) Uani 1 1 d . . . . .
C9 C 0.32398(10) 0.70874(19) 0.23044(11) 0.0385(5) Uani 1 1 d . . . . .
C10 C 0.30389(10) 0.8262(2) 0.27386(12) 0.0405(5) Uani 1 1 d . . . . .
C11 C 0.27200(12) 0.9543(2) 0.24782(14) 0.0529(6) Uani 1 1 d . . . . .
H11 H 0.2593 0.9806 0.1950 0.063 Uiso 1 1 calc R U . . .
C12 C 0.25855(13) 1.0451(2) 0.29981(18) 0.0649(7) Uani 1 1 d . . . . .
C13 C 0.2236(2) 1.1869(3) 0.2710(2) 0.1081(11) Uani 1 1 d . . . . .
H13A H 0.1889 1.2086 0.2948 0.162 Uiso 1 1 calc R U . . .
H13B H 0.1971 1.1856 0.2138 0.162 Uiso 1 1 calc R U . . .
H13C H 0.2626 1.2563 0.2861 0.162 Uiso 1 1 calc R U . . .
C14 C 0.27813(14) 1.0037(3) 0.37772(18) 0.0689(7) Uani 1 1 d . . . . .
H14 H 0.2695 1.0645 0.4128 0.083 Uiso 1 1 calc R U . . .
C15 C 0.31025(13) 0.8745(3) 0.40601(14) 0.0606(7) Uani 1 1 d . . . . .
H15 H 0.3228 0.8476 0.4587 0.073 Uiso 1 1 calc R U . . .
C16 C 0.32268(10) 0.7884(2) 0.35271(12) 0.0441(5) Uani 1 1 d . . . . .
C17 C 0.48531(11) 0.7338(2) 0.16715(12) 0.0496(5) Uani 1 1 d . U . . .
C18 C 0.53107(12) 0.6822(3) 0.13095(13) 0.0577(6) Uani 1 1 d . U . . .
H18 H 0.5737 0.7304 0.1335 0.069 Uiso 1 1 calc R U . . .
C19 C 0.51074(13) 0.5584(3) 0.09173(13) 0.0596(6) Uani 1 1 d . U . . .
H19 H 0.5404 0.5212 0.0673 0.072 Uiso 1 1 calc R U . . .
C20 C 0.44667(12) 0.4857(3) 0.08700(13) 0.0563(6) Uani 1 1 d . U . . .
H20 H 0.4341 0.4021 0.0589 0.068 Uiso 1 1 calc R U . . .
C21 C 0.40185(12) 0.5361(2) 0.12339(12) 0.0480(5) Uani 1 1 d . U . . .
H21 H 0.3594 0.4868 0.1203 0.058 Uiso 1 1 calc R U . . .
C22 C 0.42094(10) 0.6617(2) 0.16490(11) 0.0418(5) Uani 1 1 d . U . . .
C23 C 0.38986(10) 0.7457(2) 0.20963(11) 0.0422(5) Uani 1 1 d . U . . .
C24 C 0.43488(11) 0.8595(2) 0.23508(13) 0.0548(6) Uani 1 1 d . U . . .
H24 H 0.4278 0.9316 0.2653 0.066 Uiso 1 1 calc R U . . .
C25 C 0.15659(12) 0.4958(2) 0.08799(13) 0.0506(6) Uani 1 1 d . . . . .
H25 H 0.1321 0.4125 0.0883 0.061 Uiso 1 1 calc R U . . .
C26 C 0.21758(11) 0.5371(2) 0.15601(13) 0.0460(5) Uani 1 1 d . . . . .
H26 H 0.2329 0.4824 0.2019 0.055 Uiso 1 1 calc R U . . .
C27 C 0.25614(10) 0.6586(2) 0.15677(12) 0.0386(5) Uani 1 1 d . . . . .
C28 C 0.23210(11) 0.7366(2) 0.08729(12) 0.0499(6) Uani 1 1 d . . . . .
H28 H 0.2578 0.8179 0.0861 0.060 Uiso 1 1 calc R U . . .
C29 C 0.17063(12) 0.6962(2) 0.01975(13) 0.0574(6) Uani 1 1 d . . . . .
H29 H 0.1554 0.7505 -0.0263 0.069 Uiso 1 1 calc R U . . .
C30 C 0.13154(11) 0.5758(2) 0.01995(13) 0.0489(6) Uani 1 1 d . . . . .
C31 C 0.01692(12) 0.6102(2) -0.10466(13) 0.0504(6) Uani 1 1 d . . . . .
C32 C 0.00641(13) 0.7558(3) -0.08129(17) 0.0606(6) Uani 1 1 d . . . . .
C33 C -0.0060(2) 0.9925(3) -0.1173(2) 0.1204(13) Uani 1 1 d . . . . .
H33A H -0.0568 1.0008 -0.1212 0.181 Uiso 1 1 calc R U . . .
H33B H 0.0007 1.0530 -0.1558 0.181 Uiso 1 1 calc R U . . .
H33C H 0.0287 1.0183 -0.0644 0.181 Uiso 1 1 calc R U . . .
C34 C -0.03410(12) 0.5609(2) -0.17463(13) 0.0538(6) Uani 1 1 d . . . . .
H34 H -0.0661 0.6239 -0.2115 0.065 Uiso 1 1 calc R U . . .
C35 C -0.04120(12) 0.4155(3) -0.19462(13) 0.0532(6) Uani 1 1 d . . . . .
C36 C -0.11941(14) 0.2439(3) -0.27966(16) 0.0748(8) Uani 1 1 d . . . . .
H36A H -0.0753 0.1982 -0.2795 0.112 Uiso 1 1 calc R U . . .
H36B H -0.1599 0.2354 -0.3317 0.112 Uiso 1 1 calc R U . . .
H36C H -0.1340 0.2013 -0.2405 0.112 Uiso 1 1 calc R U . . .
N1 N 0.35347(9) 0.65270(19) 0.36561(10) 0.0491(5) Uani 1 1 d . . . . .
N2 N 0.49210(10) 0.8529(2) 0.20984(11) 0.0616(5) Uani 1 1 d . U . . .
H2A H 0.5270 0.9145 0.2194 0.074 Uiso 1 1 calc R U . . .
N3 N 0.06896(10) 0.53002(19) -0.04786(11) 0.0629(6) Uani 1 1 d . . . . .
H3A H 0.0631 0.4412 -0.0539 0.076 Uiso 1 1 calc R U . . .
O1 O 0.37638(8) 0.48097(16) 0.29180(9) 0.0575(4) Uani 1 1 d . . . . .
O2 O -0.00581(13) 0.78069(19) -0.02381(13) 0.0936(6) Uani 1 1 d . . . . .
O3 O 0.00813(11) 0.84867(18) -0.13322(11) 0.0812(5) Uani 1 1 d . . . . .
O4 O 0.00169(9) 0.32421(17) -0.15684(10) 0.0727(5) Uani 1 1 d . . . . .
O5 O -0.10315(8) 0.38887(17) -0.26060(9) 0.0639(4) 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
C1 C6 1.366(4) . ?
C1 C2 1.387(4) . ?
C1 H1 0.9300 . ?
C2 C3 1.382(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.384(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.386(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.391(4) . ?
C5 H5 0.9300 . ?
C1' C6 1.392(4) . ?
C1' C2' 1.394(4) . ?
C1' H1' 0.9300 . ?
C2' C3' 1.385(4) . ?
C2' H2' 0.9300 . ?
C3' C4' 1.376(4) . ?
C3' H3' 0.9300 . ?
C4' C5' 1.385(4) . ?
C4' H4' 0.9300 . ?
C5' C6 1.394(4) . ?
C5' H5' 0.9300 . ?
C6 C7 1.501(3) . ?
C7 N1 1.454(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 O1 1.221(2) . ?
C8 N1 1.360(3) . ?
C8 C9 1.544(3) . ?
C9 C23 1.515(3) . ?
C9 C10 1.517(3) . ?
C9 C27 1.529(3) . ?
C10 C11 1.371(3) . ?
C10 C16 1.385(3) . ?
C11 C12 1.389(3) . ?
C11 H11 0.9300 . ?
C12 C14 1.376(4) . ?
C12 C13 1.516(4) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 C15 1.388(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.371(3) . ?
C15 H15 0.9300 . ?
C16 N1 1.411(3) . ?
C17 N2 1.360(3) . ?
C17 C18 1.394(3) . ?
C17 C22 1.412(3) . ?
C18 C19 1.360(3) . ?
C18 H18 0.9300 . ?
C19 C20 1.396(3) . ?
C19 H19 0.9300 . ?
C20 C21 1.378(3) . ?
C20 H20 0.9300 . ?
C21 C22 1.392(3) . ?
C21 H21 0.9300 . ?
C22 C23 1.442(3) . ?
C23 C24 1.357(3) . ?
C24 N2 1.364(3) . ?
C24 H24 0.9300 . ?
C25 C30 1.372(3) . ?
C25 C26 1.382(3) . ?
C25 H25 0.9300 . ?
C26 C27 1.381(3) . ?
C26 H26 0.9300 . ?
C27 C28 1.382(3) . ?
C28 C29 1.379(3) . ?
C28 H28 0.9300 . ?
C29 C30 1.382(3) . ?
C29 H29 0.9300 . ?
C30 N3 1.408(3) . ?
C31 C34 1.346(3) . ?
C31 N3 1.355(3) . ?
C31 C32 1.499(3) . ?
C32 O2 1.191(3) . ?
C32 O3 1.312(3) . ?
C33 O3 1.458(3) . ?
C33 H33A 0.9600 . ?
C33 H33B 0.9600 . ?
C33 H33C 0.9600 . ?
C34 C35 1.434(3) . ?
C34 H34 0.9300 . ?
C35 O4 1.212(3) . ?
C35 O5 1.337(2) . ?
C36 O5 1.436(3) . ?
C36 H36A 0.9600 . ?
C36 H36B 0.9600 . ?
C36 H36C 0.9600 . ?
N2 H2A 0.8600 . ?
N3 H3A 0.8600 . ?

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
C6 C1 C2 119.5(5) . . ?
C6 C1 H1 120.2 . . ?
C2 C1 H1 120.2 . . ?
C3 C2 C1 119.1(5) . . ?
C3 C2 H2 120.5 . . ?
C1 C2 H2 120.5 . . ?
C2 C3 C4 121.1(5) . . ?
C2 C3 H3 119.4 . . ?
C4 C3 H3 119.4 . . ?
C3 C4 C5 119.9(5) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 H4 120.1 . . ?
C4 C5 C6 118.2(4) . . ?
C4 C5 H5 120.9 . . ?
C6 C5 H5 120.9 . . ?
C6 C1' C2' 122.5(5) . . ?
C6 C1' H1' 118.8 . . ?
C2' C1' H1' 118.8 . . ?
C3' C2' C1' 119.1(5) . . ?
C3' C2' H2' 120.5 . . ?
C1' C2' H2' 120.5 . . ?
C4' C3' C2' 119.9(4) . . ?
C4' C3' H3' 120.1 . . ?
C2' C3' H3' 120.1 . . ?
C3' C4' C5' 120.0(5) . . ?
C3' C4' H4' 120.0 . . ?
C5' C4' H4' 120.0 . . ?
C4' C5' C6 122.2(5) . . ?
C4' C5' H5' 118.9 . . ?
C6 C5' H5' 118.9 . . ?
C1 C6 C5 121.9(4) . . ?
C1' C6 C5' 116.2(4) . . ?
C1 C6 C7 128.8(3) . . ?
C5 C6 C7 109.2(4) . . ?
C1' C6 C7 117.7(3) . . ?
C5' C6 C7 126.0(4) . . ?
N1 C7 C6 115.79(19) . . ?
N1 C7 H7A 108.3 . . ?
C6 C7 H7A 108.3 . . ?
N1 C7 H7B 108.3 . . ?
C6 C7 H7B 108.3 . . ?
H7A C7 H7B 107.4 . . ?
O1 C8 N1 124.4(2) . . ?
O1 C8 C9 126.88(19) . . ?
N1 C8 C9 108.67(18) . . ?
C23 C9 C10 112.27(15) . . ?
C23 C9 C27 111.31(15) . . ?
C10 C9 C27 112.55(15) . . ?
C23 C9 C8 106.10(15) . . ?
C10 C9 C8 101.04(15) . . ?
C27 C9 C8 113.02(16) . . ?
C11 C10 C16 119.20(19) . . ?
C11 C10 C9 131.21(19) . . ?
C16 C10 C9 109.59(17) . . ?
C10 C11 C12 120.5(2) . . ?
C10 C11 H11 119.8 . . ?
C12 C11 H11 119.8 . . ?
C14 C12 C11 118.6(2) . . ?
C14 C12 C13 121.1(2) . . ?
C11 C12 C13 120.4(3) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C12 C14 C15 122.5(2) . . ?
C12 C14 H14 118.8 . . ?
C15 C14 H14 118.8 . . ?
C16 C15 C14 117.0(2) . . ?
C16 C15 H15 121.5 . . ?
C14 C15 H15 121.5 . . ?
C15 C16 C10 122.3(2) . . ?
C15 C16 N1 128.4(2) . . ?
C10 C16 N1 109.32(18) . . ?
N2 C17 C18 129.6(2) . . ?
N2 C17 C22 107.87(18) . . ?
C18 C17 C22 122.5(2) . . ?
C19 C18 C17 117.1(2) . . ?
C19 C18 H18 121.4 . . ?
C17 C18 H18 121.4 . . ?
C18 C19 C20 122.0(2) . . ?
C18 C19 H19 119.0 . . ?
C20 C19 H19 119.0 . . ?
C21 C20 C19 120.9(2) . . ?
C21 C20 H20 119.6 . . ?
C19 C20 H20 119.6 . . ?
C20 C21 C22 119.1(2) . . ?
C20 C21 H21 120.4 . . ?
C22 C21 H21 120.4 . . ?
C21 C22 C17 118.42(19) . . ?
C21 C22 C23 135.46(18) . . ?
C17 C22 C23 106.11(18) . . ?
C24 C23 C22 106.59(17) . . ?
C24 C23 C9 126.33(18) . . ?
C22 C23 C9 126.89(17) . . ?
C23 C24 N2 110.15(19) . . ?
C23 C24 H24 124.9 . . ?
N2 C24 H24 124.9 . . ?
C30 C25 C26 121.00(19) . . ?
C30 C25 H25 119.5 . . ?
C26 C25 H25 119.5 . . ?
C27 C26 C25 120.9(2) . . ?
C27 C26 H26 119.6 . . ?
C25 C26 H26 119.6 . . ?
C26 C27 C28 117.90(18) . . ?
C26 C27 C9 122.87(18) . . ?
C28 C27 C9 119.23(17) . . ?
C29 C28 C27 121.19(19) . . ?
C29 C28 H28 119.4 . . ?
C27 C28 H28 119.4 . . ?
C28 C29 C30 120.5(2) . . ?
C28 C29 H29 119.7 . . ?
C30 C29 H29 119.7 . . ?
C25 C30 C29 118.47(19) . . ?
C25 C30 N3 119.10(19) . . ?
C29 C30 N3 122.4(2) . . ?
C34 C31 N3 124.1(2) . . ?
C34 C31 C32 117.7(2) . . ?
N3 C31 C32 117.1(2) . . ?
O2 C32 O3 125.1(2) . . ?
O2 C32 C31 122.4(2) . . ?
O3 C32 C31 112.3(2) . . ?
O3 C33 H33A 109.5 . . ?
O3 C33 H33B 109.5 . . ?
H33A C33 H33B 109.5 . . ?
O3 C33 H33C 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
C31 C34 C35 122.8(2) . . ?
C31 C34 H34 118.6 . . ?
C35 C34 H34 118.6 . . ?
O4 C35 O5 122.3(2) . . ?
O4 C35 C34 125.7(2) . . ?
O5 C35 C34 112.0(2) . . ?
O5 C36 H36A 109.5 . . ?
O5 C36 H36B 109.5 . . ?
H36A C36 H36B 109.5 . . ?
O5 C36 H36C 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
C8 N1 C16 111.27(17) . . ?
C8 N1 C7 122.99(19) . . ?
C16 N1 C7 125.44(19) . . ?
C17 N2 C24 109.28(18) . . ?
C17 N2 H2A 125.4 . . ?
C24 N2 H2A 125.4 . . ?
C31 N3 C30 127.30(18) . . ?
C31 N3 H3A 116.4 . . ?
C30 N3 H3A 116.4 . . ?
C32 O3 C33 115.8(2) . . ?
C35 O5 C36 115.60(19) . . ?

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
N2 H2A O1 0.86 2.07 2.840(2) 149.4 2_655
N3 H3A O4 0.86 2.10 2.731(2) 130.0 .

_refine_diff_density_max         0.141
_refine_diff_density_min         -0.211
_refine_diff_density_rms         0.040

####################################################################### 
# 
# 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_4e
_database_code_depnum_ccdc_archive 'CCDC 2296938'
loop_
_audit_author_name
_audit_author_address
'Chao-Guo Yan' 'Yangzhou University'
_audit_update_record             
;
2023-09-23 deposited with the CCDC.	2023-11-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C38 H33 N3 O5'
_chemical_formula_sum            'C38 H33 N3 O5'
_chemical_formula_weight         611.67

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

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

_cell_length_a                   13.5696(13)
_cell_length_b                   9.6679(10)
_cell_length_c                   24.307(3)
_cell_angle_alpha                90
_cell_angle_beta                 92.204(3)
_cell_angle_gamma                90
_cell_volume                     3186.5(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    7003
_cell_measurement_theta_min      2.27
_cell_measurement_theta_max      23.94

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.275
_exptl_crystal_F_000             1288
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    0.085
_shelx_estimated_absorpt_T_min   0.977
_shelx_estimated_absorpt_T_max   0.985
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6711
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            26143
_diffrn_reflns_av_unetI/netI     0.0648
_diffrn_reflns_av_R_equivalents  0.0548
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         2.693
_diffrn_reflns_theta_max         25.997
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             6236
_reflns_number_gt                3569
_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0690P)²+2.6512P] 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         6236
_refine_ls_number_parameters     449
_refine_ls_number_restraints     74
_refine_ls_R_factor_all          0.1346
_refine_ls_R_factor_gt           0.0683
_refine_ls_wR_factor_ref         0.1872
_refine_ls_wR_factor_gt          0.1578
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.037
_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
C1 C 0.5682(2) 0.2668(3) 0.24281(14) 0.0530(8) Uani 1 1 d . . . . .
H1 H 0.5247 0.1997 0.2291 0.064 Uiso 1 1 calc R U . . .
C2 C 0.6253(2) 0.2420(4) 0.29052(14) 0.0591(9) Uani 1 1 d . . . . .
H2 H 0.6199 0.1570 0.3081 0.071 Uiso 1 1 calc R U . . .
C3 C 0.6893(2) 0.3389(4) 0.31246(13) 0.0510(8) Uani 1 1 d . . . . .
C4 C 0.7478(3) 0.3115(5) 0.36547(15) 0.0768(12) Uani 1 1 d . . . . .
H4A H 0.7881 0.2308 0.3612 0.115 Uiso 1 1 calc R U . . .
H4B H 0.7034 0.2965 0.3947 0.115 Uiso 1 1 calc R U . . .
H4C H 0.7891 0.3897 0.3742 0.115 Uiso 1 1 calc R U . . .
C5 C 0.6972(2) 0.4620(4) 0.28433(14) 0.0589(9) Uani 1 1 d . . . . .
H5 H 0.7410 0.5289 0.2978 0.071 Uiso 1 1 calc R U . . .
C6 C 0.6416(2) 0.4888(3) 0.23659(13) 0.0500(8) Uani 1 1 d . . . . .
H6 H 0.6484 0.5728 0.2185 0.060 Uiso 1 1 calc R U . . .
C7 C 0.5765(2) 0.3912(3) 0.21598(12) 0.0396(7) Uani 1 1 d . . . . .
C8 C 0.5396(2) 0.3568(3) 0.11790(12) 0.0412(7) Uani 1 1 d . . . . .
C9 C 0.6365(2) 0.2798(4) 0.12084(13) 0.0520(8) Uani 1 1 d . . . . .
C10 C 0.8079(3) 0.2995(6) 0.1152(2) 0.0992(14) Uani 1 1 d . U . . .
H10A H 0.8482 0.3380 0.0869 0.119 Uiso 0.500(10) 1 calc R U P A 1
H10B H 0.8014 0.2007 0.1090 0.119 Uiso 0.500(10) 1 calc R U P A 1
H10C H 0.8075 0.2228 0.1410 0.119 Uiso 0.500(10) 1 calc R U P A 2
H10D H 0.8203 0.2620 0.0791 0.119 Uiso 0.500(10) 1 calc R U P A 2
C11 C 0.8536(7) 0.3257(11) 0.1698(5) 0.098(3) Uani 0.500(10) 1 d . U P A 1
H11A H 0.8634 0.4234 0.1747 0.147 Uiso 0.500(10) 1 calc R U P A 1
H11B H 0.9160 0.2792 0.1730 0.147 Uiso 0.500(10) 1 calc R U P A 1
H11C H 0.8113 0.2918 0.1976 0.147 Uiso 0.500(10) 1 calc R U P A 1
C11' C 0.8835(7) 0.3880(12) 0.1306(5) 0.101(3) Uani 0.500(10) 1 d . U P A 2
H11D H 0.8740 0.4750 0.1121 0.151 Uiso 0.500(10) 1 calc R U P A 2
H11E H 0.9452 0.3484 0.1207 0.151 Uiso 0.500(10) 1 calc R U P A 2
H11F H 0.8839 0.4022 0.1697 0.151 Uiso 0.500(10) 1 calc R U P A 2
C12 C 0.4809(2) 0.3620(3) 0.07066(12) 0.0471(8) Uani 1 1 d . . . . .
C13 C 0.5065(3) 0.3024(4) 0.01803(14) 0.0564(9) Uani 1 1 d . . . . .
C14 C 0.6176(9) 0.177(2) -0.0322(7) 0.0823(18) Uani 0.618(8) 1 d . U P B 1
H14A H 0.6291 0.2436 -0.0611 0.099 Uiso 0.618(8) 1 calc R U P B 1
H14B H 0.5637 0.1168 -0.0441 0.099 Uiso 0.618(8) 1 calc R U P B 1
C15 C 0.7090(7) 0.0951(10) -0.0186(3) 0.113(2) Uani 0.618(8) 1 d . U P B 1
H15A H 0.7584 0.1547 -0.0020 0.170 Uiso 0.618(8) 1 calc R U P B 1
H15B H 0.7333 0.0557 -0.0517 0.170 Uiso 0.618(8) 1 calc R U P B 1
H15C H 0.6940 0.0225 0.0067 0.170 Uiso 0.618(8) 1 calc R U P B 1
C14' C 0.6390(17) 0.174(3) -0.0302(12) 0.0830(19) Uani 0.382(8) 1 d . U P B 2
H14C H 0.6196 0.2227 -0.0639 0.100 Uiso 0.382(8) 1 calc R U P B 2
H14D H 0.7105 0.1759 -0.0264 0.100 Uiso 0.382(8) 1 calc R U P B 2
C15' C 0.6062(12) 0.0400(14) -0.0328(5) 0.106(3) Uani 0.382(8) 1 d . U P B 2
H15D H 0.6273 -0.0081 0.0001 0.158 Uiso 0.382(8) 1 calc R U P B 2
H15E H 0.6330 -0.0050 -0.0642 0.158 Uiso 0.382(8) 1 calc R U P B 2
H15F H 0.5355 0.0391 -0.0363 0.158 Uiso 0.382(8) 1 calc R U P B 2
C16 C 0.4602(3) 0.5151(4) 0.36647(14) 0.0564(9) Uani 1 1 d . . . . .
H16 H 0.4830 0.4583 0.3388 0.068 Uiso 1 1 calc R U . . .
C17 C 0.5196(3) 0.5413(4) 0.41283(16) 0.0694(11) Uani 1 1 d . . . . .
H17 H 0.5819 0.5014 0.4162 0.083 Uiso 1 1 calc R U . . .
C18 C 0.4879(4) 0.6247(4) 0.45340(16) 0.0751(12) Uani 1 1 d . . . . .
H18 H 0.5282 0.6416 0.4845 0.090 Uiso 1 1 calc R U . . .
C19 C 0.3973(4) 0.6833(4) 0.44837(16) 0.0814(13) Uani 1 1 d . . . . .
H19 H 0.3752 0.7405 0.4761 0.098 Uiso 1 1 calc R U . . .
C20 C 0.3374(3) 0.6582(4) 0.40201(15) 0.0665(10) Uani 1 1 d . . . . .
H20 H 0.2758 0.7000 0.3987 0.080 Uiso 1 1 calc R U . . .
C21 C 0.3676(2) 0.5725(3) 0.36096(12) 0.0466(8) Uani 1 1 d . . . . .
C22 C 0.3018(2) 0.5412(4) 0.31089(12) 0.0498(8) Uani 1 1 d . . . . .
H22A H 0.2749 0.4488 0.3144 0.060 Uiso 1 1 calc R U . . .
H22B H 0.2471 0.6058 0.3095 0.060 Uiso 1 1 calc R U . . .
C23 C 0.3694(2) 0.4422(3) 0.22520(12) 0.0404(7) Uani 1 1 d . . . . .
C24 C 0.4245(2) 0.4989(3) 0.17441(12) 0.0393(7) Uani 1 1 d . . . . .
C25 C 0.4436(2) 0.6476(3) 0.19175(12) 0.0375(7) Uani 1 1 d . . . . .
C26 C 0.4900(2) 0.7522(3) 0.16429(13) 0.0471(8) Uani 1 1 d . . . . .
H26 H 0.5201 0.7355 0.1312 0.057 Uiso 1 1 calc R U . . .
C27 C 0.4904(2) 0.8840(3) 0.18778(14) 0.0550(9) Uani 1 1 d . . . . .
H27 H 0.5221 0.9565 0.1706 0.066 Uiso 1 1 calc R U . . .
C28 C 0.4436(2) 0.9071(3) 0.23658(14) 0.0549(9) Uani 1 1 d . . . . .
H28 H 0.4442 0.9958 0.2514 0.066 Uiso 1 1 calc R U . . .
C29 C 0.3963(2) 0.8030(3) 0.26391(13) 0.0467(8) Uani 1 1 d . . . . .
H29 H 0.3648 0.8197 0.2965 0.056 Uiso 1 1 calc R U . . .
C30 C 0.3977(2) 0.6730(3) 0.24074(12) 0.0384(7) Uani 1 1 d . . . . .
C31 C 0.3876(2) 0.4299(3) 0.07633(12) 0.0459(8) Uani 1 1 d . . . . .
C32 C 0.3588(2) 0.4895(3) 0.12375(12) 0.0415(7) Uani 1 1 d . . . . .
C33 C 0.2606(2) 0.5432(3) 0.11406(13) 0.0457(8) Uani 1 1 d . . . . .
C34 C 0.1927(2) 0.6142(4) 0.14566(15) 0.0582(9) Uani 1 1 d . . . . .
H34 H 0.2082 0.6367 0.1822 0.070 Uiso 1 1 calc R U . . .
C35 C 0.1032(3) 0.6498(4) 0.12176(18) 0.0711(11) Uani 1 1 d . . . . .
H35 H 0.0577 0.6967 0.1425 0.085 Uiso 1 1 calc R U . . .
C36 C 0.0790(3) 0.6173(4) 0.06733(19) 0.0764(12) Uani 1 1 d . . . . .
H36 H 0.0173 0.6423 0.0526 0.092 Uiso 1 1 calc R U . . .
C37 C 0.1437(3) 0.5490(4) 0.03453(16) 0.0685(11) Uani 1 1 d . . . . .
H37 H 0.1273 0.5286 -0.0021 0.082 Uiso 1 1 calc R U . . .
C38 C 0.2349(3) 0.5117(3) 0.05857(14) 0.0547(9) Uani 1 1 d . . . . .
N1 N 0.51559(17) 0.4168(2) 0.16660(9) 0.0415(6) Uani 1 1 d . . . . .
N2 N 0.35376(17) 0.5502(2) 0.25978(10) 0.0412(6) Uani 1 1 d . . . . .
N3 N 0.3132(2) 0.4425(3) 0.03634(11) 0.0559(7) Uani 1 1 d . . . . .
H3 H 0.3151 0.4123 0.0031 0.067 Uiso 1 1 calc R U . . .
O1 O 0.64250(19) 0.1583(3) 0.13050(10) 0.0702(7) Uani 1 1 d . . . . .
O2 O 0.71057(17) 0.3651(3) 0.11342(10) 0.0691(7) Uani 1 1 d . . . . .
O3 O 0.4518(2) 0.3046(3) -0.02284(10) 0.0798(8) Uani 1 1 d . . . . .
O4 O 0.5959(2) 0.2456(3) 0.01796(10) 0.0758(8) Uani 1 1 d . U . . .
O5 O 0.34322(15) 0.3233(2) 0.23152(9) 0.0526(6) 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
C1 C7 1.375(4) . ?
C1 C2 1.391(5) . ?
C1 H1 0.9300 . ?
C2 C3 1.372(5) . ?
C2 H2 0.9300 . ?
C3 C5 1.379(5) . ?
C3 C4 1.511(5) . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C5 C6 1.384(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.375(4) . ?
C6 H6 0.9300 . ?
C7 N1 1.452(4) . ?
C8 N1 1.369(4) . ?
C8 C12 1.373(4) . ?
C8 C9 1.511(4) . ?
C9 O1 1.200(4) . ?
C9 O2 1.317(4) . ?
C10 C11' 1.376(10) . ?
C10 O2 1.464(5) . ?
C10 C11 1.465(11) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 H10C 0.9700 . ?
C10 H10D 0.9700 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C11' H11D 0.9600 . ?
C11' H11E 0.9600 . ?
C11' H11F 0.9600 . ?
C12 C31 1.437(4) . ?
C12 C13 1.457(4) . ?
C13 O3 1.218(4) . ?
C13 O4 1.331(4) . ?
C14 O4 1.428(18) . ?
C14 C15 1.498(17) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C14' C15' 1.37(4) . ?
C14' O4 1.50(3) . ?
C14' H14C 0.9700 . ?
C14' H14D 0.9700 . ?
C15' H15D 0.9600 . ?
C15' H15E 0.9600 . ?
C15' H15F 0.9600 . ?
C16 C21 1.375(5) . ?
C16 C17 1.384(5) . ?
C16 H16 0.9300 . ?
C17 C18 1.357(5) . ?
C17 H17 0.9300 . ?
C18 C19 1.355(6) . ?
C18 H18 0.9300 . ?
C19 C20 1.385(5) . ?
C19 H19 0.9300 . ?
C20 C21 1.371(5) . ?
C20 H20 0.9300 . ?
C21 C22 1.512(4) . ?
C22 N2 1.454(4) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C23 O5 1.215(3) . ?
C23 N2 1.362(4) . ?
C23 C24 1.567(4) . ?
C24 N1 1.487(4) . ?
C24 C32 1.495(4) . ?
C24 C25 1.518(4) . ?
C25 C26 1.377(4) . ?
C25 C30 1.386(4) . ?
C26 C27 1.397(4) . ?
C26 H26 0.9300 . ?
C27 C28 1.384(5) . ?
C27 H27 0.9300 . ?
C28 C29 1.378(4) . ?
C28 H28 0.9300 . ?
C29 C30 1.378(4) . ?
C29 H29 0.9300 . ?
C30 N2 1.414(4) . ?
C31 C32 1.360(4) . ?
C31 N3 1.380(4) . ?
C32 C33 1.441(4) . ?
C33 C34 1.401(5) . ?
C33 C38 1.413(4) . ?
C34 C35 1.370(5) . ?
C34 H34 0.9300 . ?
C35 C36 1.387(5) . ?
C35 H35 0.9300 . ?
C36 C37 1.377(6) . ?
C36 H36 0.9300 . ?
C37 C38 1.396(5) . ?
C37 H37 0.9300 . ?
C38 N3 1.383(4) . ?
N3 H3 0.8600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 C1 C2 119.6(3) . . ?
C7 C1 H1 120.2 . . ?
C2 C1 H1 120.2 . . ?
C3 C2 C1 122.0(3) . . ?
C3 C2 H2 119.0 . . ?
C1 C2 H2 119.0 . . ?
C2 C3 C5 117.2(3) . . ?
C2 C3 C4 121.1(3) . . ?
C5 C3 C4 121.8(3) . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C3 C5 C6 121.9(3) . . ?
C3 C5 H5 119.1 . . ?
C6 C5 H5 119.1 . . ?
C7 C6 C5 119.9(3) . . ?
C7 C6 H6 120.0 . . ?
C5 C6 H6 120.0 . . ?
C1 C7 C6 119.4(3) . . ?
C1 C7 N1 119.2(3) . . ?
C6 C7 N1 121.4(3) . . ?
N1 C8 C12 124.0(3) . . ?
N1 C8 C9 113.8(3) . . ?
C12 C8 C9 122.2(3) . . ?
O1 C9 O2 126.4(3) . . ?
O1 C9 C8 122.9(3) . . ?
O2 C9 C8 110.7(3) . . ?
C11' C10 O2 113.6(6) . . ?
O2 C10 C11 107.6(5) . . ?
O2 C10 H10A 110.2 . . ?
C11 C10 H10A 110.2 . . ?
O2 C10 H10B 110.2 . . ?
C11 C10 H10B 110.2 . . ?
H10A C10 H10B 108.5 . . ?
C11' C10 H10C 108.8 . . ?
O2 C10 H10C 108.8 . . ?
C11' C10 H10D 108.8 . . ?
O2 C10 H10D 108.8 . . ?
H10C C10 H10D 107.7 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C11' H11D 109.5 . . ?
C10 C11' H11E 109.5 . . ?
H11D C11' H11E 109.5 . . ?
C10 C11' H11F 109.5 . . ?
H11D C11' H11F 109.5 . . ?
H11E C11' H11F 109.5 . . ?
C8 C12 C31 114.9(3) . . ?
C8 C12 C13 124.7(3) . . ?
C31 C12 C13 120.4(3) . . ?
O3 C13 O4 122.2(3) . . ?
O3 C13 C12 123.4(3) . . ?
O4 C13 C12 114.4(3) . . ?
O4 C14 C15 104.7(10) . . ?
O4 C14 H14A 110.8 . . ?
C15 C14 H14A 110.8 . . ?
O4 C14 H14B 110.8 . . ?
C15 C14 H14B 110.8 . . ?
H14A C14 H14B 108.9 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C15' C14' O4 109.6(19) . . ?
C15' C14' H14C 109.8 . . ?
O4 C14' H14C 109.8 . . ?
C15' C14' H14D 109.8 . . ?
O4 C14' H14D 109.8 . . ?
H14C C14' H14D 108.2 . . ?
C14' C15' H15D 109.5 . . ?
C14' C15' H15E 109.5 . . ?
H15D C15' H15E 109.5 . . ?
C14' C15' H15F 109.5 . . ?
H15D C15' H15F 109.5 . . ?
H15E C15' H15F 109.5 . . ?
C21 C16 C17 120.5(3) . . ?
C21 C16 H16 119.8 . . ?
C17 C16 H16 119.8 . . ?
C18 C17 C16 120.6(4) . . ?
C18 C17 H17 119.7 . . ?
C16 C17 H17 119.7 . . ?
C19 C18 C17 119.7(4) . . ?
C19 C18 H18 120.2 . . ?
C17 C18 H18 120.2 . . ?
C18 C19 C20 120.1(4) . . ?
C18 C19 H19 120.0 . . ?
C20 C19 H19 120.0 . . ?
C21 C20 C19 121.1(4) . . ?
C21 C20 H20 119.5 . . ?
C19 C20 H20 119.5 . . ?
C20 C21 C16 118.0(3) . . ?
C20 C21 C22 121.5(3) . . ?
C16 C21 C22 120.4(3) . . ?
N2 C22 C21 112.7(2) . . ?
N2 C22 H22A 109.1 . . ?
C21 C22 H22A 109.1 . . ?
N2 C22 H22B 109.1 . . ?
C21 C22 H22B 109.1 . . ?
H22A C22 H22B 107.8 . . ?
O5 C23 N2 126.4(3) . . ?
O5 C23 C24 125.5(3) . . ?
N2 C23 C24 108.0(2) . . ?
N1 C24 C32 109.6(2) . . ?
N1 C24 C25 114.0(2) . . ?
C32 C24 C25 112.1(2) . . ?
N1 C24 C23 109.8(2) . . ?
C32 C24 C23 109.9(2) . . ?
C25 C24 C23 101.2(2) . . ?
C26 C25 C30 121.0(3) . . ?
C26 C25 C24 129.6(3) . . ?
C30 C25 C24 109.2(2) . . ?
C25 C26 C27 117.8(3) . . ?
C25 C26 H26 121.1 . . ?
C27 C26 H26 121.1 . . ?
C28 C27 C26 120.2(3) . . ?
C28 C27 H27 119.9 . . ?
C26 C27 H27 119.9 . . ?
C29 C28 C27 122.2(3) . . ?
C29 C28 H28 118.9 . . ?
C27 C28 H28 118.9 . . ?
C30 C29 C28 117.1(3) . . ?
C30 C29 H29 121.5 . . ?
C28 C29 H29 121.5 . . ?
C29 C30 C25 121.8(3) . . ?
C29 C30 N2 128.3(3) . . ?
C25 C30 N2 110.0(2) . . ?
C32 C31 N3 109.5(3) . . ?
C32 C31 C12 123.9(3) . . ?
N3 C31 C12 126.6(3) . . ?
C31 C32 C33 108.0(3) . . ?
C31 C32 C24 122.8(3) . . ?
C33 C32 C24 129.2(3) . . ?
C34 C33 C38 119.1(3) . . ?
C34 C33 C32 135.2(3) . . ?
C38 C33 C32 105.7(3) . . ?
C35 C34 C33 118.8(3) . . ?
C35 C34 H34 120.6 . . ?
C33 C34 H34 120.6 . . ?
C34 C35 C36 121.5(4) . . ?
C34 C35 H35 119.3 . . ?
C36 C35 H35 119.3 . . ?
C37 C36 C35 121.8(3) . . ?
C37 C36 H36 119.1 . . ?
C35 C36 H36 119.1 . . ?
C36 C37 C38 117.2(4) . . ?
C36 C37 H37 121.4 . . ?
C38 C37 H37 121.4 . . ?
N3 C38 C37 130.0(3) . . ?
N3 C38 C33 108.2(3) . . ?
C37 C38 C33 121.7(3) . . ?
C8 N1 C7 119.8(2) . . ?
C8 N1 C24 124.2(2) . . ?
C7 N1 C24 115.8(2) . . ?
C23 N2 C30 111.3(2) . . ?
C23 N2 C22 125.0(3) . . ?
C30 N2 C22 123.6(2) . . ?
C31 N3 C38 108.6(3) . . ?
C31 N3 H3 125.7 . . ?
C38 N3 H3 125.7 . . ?
C9 O2 C10 114.6(3) . . ?
C13 O4 C14 114.2(6) . . ?
C13 O4 C14' 125.1(10) . . ?

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
N3 H3 O3 0.86 2.24 2.755(4) 118.6 .

_refine_diff_density_max         0.257
_refine_diff_density_min         -0.344
_refine_diff_density_rms         0.047

####################################################################### 
# 
# 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_5a
_database_code_depnum_ccdc_archive 'CCDC 2296939'
loop_
_audit_author_name
_audit_author_address
'Chao-Guo Yan' 'Yangzhou University'
_audit_update_record             
;
2023-09-23 deposited with the CCDC.	2023-11-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C35 H29 N3 O5'
_chemical_formula_sum            'C35 H29 N3 O5'
_chemical_formula_weight         571.61

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      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                   8.803(2)
_cell_length_b                   11.433(3)
_cell_length_c                   18.190(5)
_cell_angle_alpha                106.892(8)
_cell_angle_beta                 93.952(8)
_cell_angle_gamma                94.154(8)
_cell_volume                     1739.4(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5457
_cell_measurement_theta_min      2.35
_cell_measurement_theta_max      21.84

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.091
_exptl_crystal_F_000             600
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.074
_shelx_estimated_absorpt_T_min   0.983
_shelx_estimated_absorpt_T_max   0.985
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6364
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            24438
_diffrn_reflns_av_unetI/netI     0.0940
_diffrn_reflns_av_R_equivalents  0.0735
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         1.890
_diffrn_reflns_theta_max         26.000
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             6781
_reflns_number_gt                3505
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.1255P)²+0.2249P] 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         6781
_refine_ls_number_parameters     390
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1504
_refine_ls_R_factor_gt           0.0732
_refine_ls_wR_factor_ref         0.2380
_refine_ls_wR_factor_gt          0.1966
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_restrained_S_all      1.018
_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
C1 C 0.0392(4) 0.3452(4) -0.1881(2) 0.0691(11) Uani 1 1 d . . . . .
H1 H 0.0121 0.2904 -0.1610 0.083 Uiso 1 1 calc R U . . .
C2 C -0.0156(6) 0.3204(5) -0.2640(3) 0.1036(16) Uani 1 1 d . . . . .
H2 H -0.0802 0.2497 -0.2884 0.124 Uiso 1 1 calc R U . . .
C3 C 0.0267(6) 0.4018(5) -0.3038(3) 0.1005(16) Uani 1 1 d . . . . .
H3 H -0.0101 0.3858 -0.3553 0.121 Uiso 1 1 calc R U . . .
C4 C 0.1214(6) 0.5051(5) -0.2686(3) 0.0919(14) Uani 1 1 d . . . . .
H4 H 0.1502 0.5592 -0.2959 0.110 Uiso 1 1 calc R U . . .
C5 C 0.1741(5) 0.5289(3) -0.1928(2) 0.0692(11) Uani 1 1 d . . . . .
H5 H 0.2388 0.5998 -0.1687 0.083 Uiso 1 1 calc R U . . .
C6 C 0.1333(3) 0.4500(3) -0.15147(18) 0.0450(8) Uani 1 1 d . . . . .
C7 C 0.1886(4) 0.4803(3) -0.06739(18) 0.0472(8) Uani 1 1 d . . . . .
H7A H 0.2624 0.5522 -0.0537 0.057 Uiso 1 1 calc R U . . .
H7B H 0.1027 0.5011 -0.0370 0.057 Uiso 1 1 calc R U . . .
C8 C 0.4062(3) 0.3481(3) -0.06527(16) 0.0362(7) Uani 1 1 d . . . . .
C9 C 0.5063(3) 0.3965(3) -0.10626(18) 0.0491(8) Uani 1 1 d . . . . .
H9 H 0.4831 0.4624 -0.1239 0.059 Uiso 1 1 calc R U . . .
C10 C 0.6420(4) 0.3443(3) -0.12039(19) 0.0532(9) Uani 1 1 d . . . . .
H10 H 0.7119 0.3756 -0.1476 0.064 Uiso 1 1 calc R U . . .
C11 C 0.6750(3) 0.2462(3) -0.09452(19) 0.0513(8) Uani 1 1 d . . . . .
H11 H 0.7670 0.2120 -0.1045 0.062 Uiso 1 1 calc R U . . .
C12 C 0.5740(3) 0.1984(3) -0.05429(17) 0.0444(8) Uani 1 1 d . . . . .
H12 H 0.5965 0.1314 -0.0377 0.053 Uiso 1 1 calc R U . . .
C13 C 0.4394(3) 0.2500(2) -0.03855(15) 0.0350(7) Uani 1 1 d . . . . .
C14 C 0.3067(3) 0.2178(3) 0.00430(16) 0.0353(7) Uani 1 1 d . . . . .
C15 C 0.1897(3) 0.3041(3) -0.01218(16) 0.0354(7) Uani 1 1 d . . . . .
C16 C 0.1194(3) -0.0907(3) -0.1128(2) 0.0490(8) Uani 1 1 d . . . . .
C17 C 0.0555(4) -0.1719(3) -0.1827(3) 0.0682(11) Uani 1 1 d . . . . .
H17 H 0.0052 -0.2476 -0.1851 0.082 Uiso 1 1 calc R U . . .
C18 C 0.0692(5) -0.1364(4) -0.2478(3) 0.0867(13) Uani 1 1 d . . . . .
H18 H 0.0277 -0.1895 -0.2951 0.104 Uiso 1 1 calc R U . . .
C19 C 0.1427(5) -0.0241(4) -0.2455(2) 0.0787(12) Uani 1 1 d . . . . .
H19 H 0.1498 -0.0033 -0.2910 0.094 Uiso 1 1 calc R U . . .
C20 C 0.2051(4) 0.0567(3) -0.17696(19) 0.0599(9) Uani 1 1 d . . . . .
H20 H 0.2551 0.1318 -0.1758 0.072 Uiso 1 1 calc R U . . .
C21 C 0.1931(3) 0.0255(3) -0.10895(18) 0.0426(7) Uani 1 1 d . . . . .
C22 C 0.2383(3) 0.0856(3) -0.02896(16) 0.0357(7) Uani 1 1 d . . . . .
C23 C 0.1916(3) 0.0074(3) 0.01015(19) 0.0428(8) Uani 1 1 d . . . . .
H23 H 0.2039 0.0241 0.0635 0.051 Uiso 1 1 calc R U . . .
C24 C 0.5160(4) 0.2264(3) 0.19612(19) 0.0543(9) Uani 1 1 d . . . . .
H24 H 0.5927 0.1859 0.2130 0.065 Uiso 1 1 calc R U . . .
C25 C 0.4665(3) 0.1937(3) 0.11955(18) 0.0476(8) Uani 1 1 d . . . . .
H25 H 0.5089 0.1300 0.0854 0.057 Uiso 1 1 calc R U . . .
C26 C 0.3538(3) 0.2534(3) 0.09103(17) 0.0387(7) Uani 1 1 d . . . . .
C27 C 0.2925(3) 0.3461(3) 0.14465(18) 0.0452(8) Uani 1 1 d . . . . .
H27 H 0.2162 0.3872 0.1279 0.054 Uiso 1 1 calc R U . . .
C28 C 0.3416(4) 0.3790(3) 0.22205(19) 0.0552(9) Uani 1 1 d . . . . .
H28 H 0.2991 0.4423 0.2566 0.066 Uiso 1 1 calc R U . . .
C29 C 0.4534(4) 0.3190(3) 0.24888(19) 0.0524(9) Uani 1 1 d . . . . .
C30 C 0.5603(4) 0.2874(4) 0.3701(2) 0.0628(10) Uani 1 1 d . . . . .
C31 C 0.5092(6) 0.1531(4) 0.3474(2) 0.0737(11) Uani 1 1 d . . . . .
C32 C 0.3100(7) 0.0002(4) 0.2844(4) 0.146(2) Uani 1 1 d . . . . .
H32A H 0.3813 -0.0431 0.2515 0.220 Uiso 1 1 calc R U . . .
H32B H 0.2126 -0.0078 0.2553 0.220 Uiso 1 1 calc R U . . .
H32C H 0.2987 -0.0339 0.3264 0.220 Uiso 1 1 calc R U . . .
C33 C 0.6514(5) 0.3336(4) 0.4370(2) 0.0753(11) Uani 1 1 d . . . . .
H33 H 0.6826 0.2791 0.4630 0.090 Uiso 1 1 calc R U . . .
C34 C 0.7023(5) 0.4600(4) 0.4699(2) 0.0741(11) Uani 1 1 d . . . . .
C35 C 0.8565(6) 0.6086(5) 0.5699(3) 0.1140(18) Uani 1 1 d . . . . .
H35A H 0.7734 0.6561 0.5874 0.171 Uiso 1 1 calc R U . . .
H35B H 0.9071 0.6406 0.5338 0.171 Uiso 1 1 calc R U . . .
H35C H 0.9279 0.6130 0.6132 0.171 Uiso 1 1 calc R U . . .
N1 N 0.2589(3) 0.3810(2) -0.04716(14) 0.0405(6) Uani 1 1 d . . . . .
N2 N 0.1239(3) -0.0995(2) -0.04014(17) 0.0489(7) Uani 1 1 d . . . . .
H2A H 0.0894 -0.1628 -0.0277 0.059 Uiso 1 1 calc R U . . .
N3 N 0.5034(4) 0.3572(3) 0.32855(16) 0.0695(9) Uani 1 1 d . . . . .
H3A H 0.4967 0.4330 0.3531 0.083 Uiso 1 1 calc R U . . .
O1 O 0.0567(2) 0.30480(18) 0.00362(12) 0.0460(5) Uani 1 1 d . . . . .
O2 O 0.5857(4) 0.0777(3) 0.35966(19) 0.1092(11) Uani 1 1 d . . . . .
O3 O 0.3663(4) 0.1291(3) 0.31475(17) 0.0873(9) Uani 1 1 d . . . . .
O4 O 0.6644(4) 0.5411(3) 0.44449(16) 0.0952(10) Uani 1 1 d . . . . .
O5 O 0.7982(4) 0.4829(3) 0.53307(17) 0.1029(10) 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
C1 C6 1.371(5) . ?
C1 C2 1.372(6) . ?
C1 H1 0.9300 . ?
C2 C3 1.381(6) . ?
C2 H2 0.9300 . ?
C3 C4 1.358(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.366(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.376(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.504(4) . ?
C7 N1 1.457(4) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.378(4) . ?
C8 C13 1.387(4) . ?
C8 N1 1.410(3) . ?
C9 C10 1.382(4) . ?
C9 H9 0.9300 . ?
C10 C11 1.378(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.370(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.373(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.529(4) . ?
C14 C22 1.517(4) . ?
C14 C26 1.529(4) . ?
C14 C15 1.549(4) . ?
C15 O1 1.225(3) . ?
C15 N1 1.360(4) . ?
C16 N2 1.353(4) . ?
C16 C17 1.391(5) . ?
C16 C21 1.416(4) . ?
C17 C18 1.368(6) . ?
C17 H17 0.9300 . ?
C18 C19 1.383(6) . ?
C18 H18 0.9300 . ?
C19 C20 1.369(5) . ?
C19 H19 0.9300 . ?
C20 C21 1.392(4) . ?
C20 H20 0.9300 . ?
C21 C22 1.431(4) . ?
C22 C23 1.353(4) . ?
C23 N2 1.362(4) . ?
C23 H23 0.9300 . ?
C24 C25 1.364(4) . ?
C24 C29 1.383(5) . ?
C24 H24 0.9300 . ?
C25 C26 1.397(4) . ?
C25 H25 0.9300 . ?
C26 C27 1.386(4) . ?
C27 C28 1.377(4) . ?
C27 H27 0.9300 . ?
C28 C29 1.379(4) . ?
C28 H28 0.9300 . ?
C29 N3 1.415(4) . ?
C30 N3 1.347(4) . ?
C30 C33 1.355(5) . ?
C30 C31 1.495(6) . ?
C31 O2 1.193(5) . ?
C31 O3 1.327(5) . ?
C32 O3 1.451(5) . ?
C32 H32A 0.9600 . ?
C32 H32B 0.9600 . ?
C32 H32C 0.9600 . ?
C33 C34 1.419(6) . ?
C33 H33 0.9300 . ?
C34 O4 1.208(5) . ?
C34 O5 1.327(5) . ?
C35 O5 1.436(5) . ?
C35 H35A 0.9600 . ?
C35 H35B 0.9600 . ?
C35 H35C 0.9600 . ?
N2 H2A 0.8600 . ?
N3 H3A 0.8600 . ?

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
C6 C1 C2 120.8(4) . . ?
C6 C1 H1 119.6 . . ?
C2 C1 H1 119.6 . . ?
C1 C2 C3 119.1(4) . . ?
C1 C2 H2 120.4 . . ?
C3 C2 H2 120.4 . . ?
C4 C3 C2 120.7(4) . . ?
C4 C3 H3 119.6 . . ?
C2 C3 H3 119.6 . . ?
C3 C4 C5 119.4(4) . . ?
C3 C4 H4 120.3 . . ?
C5 C4 H4 120.3 . . ?
C4 C5 C6 121.2(4) . . ?
C4 C5 H5 119.4 . . ?
C6 C5 H5 119.4 . . ?
C1 C6 C5 118.7(3) . . ?
C1 C6 C7 121.1(3) . . ?
C5 C6 C7 120.2(3) . . ?
N1 C7 C6 113.8(2) . . ?
N1 C7 H7A 108.8 . . ?
C6 C7 H7A 108.8 . . ?
N1 C7 H7B 108.8 . . ?
C6 C7 H7B 108.8 . . ?
H7A C7 H7B 107.7 . . ?
C9 C8 C13 121.6(3) . . ?
C9 C8 N1 128.5(3) . . ?
C13 C8 N1 109.8(2) . . ?
C8 C9 C10 118.0(3) . . ?
C8 C9 H9 121.0 . . ?
C10 C9 H9 121.0 . . ?
C11 C10 C9 120.7(3) . . ?
C11 C10 H10 119.7 . . ?
C9 C10 H10 119.7 . . ?
C12 C11 C10 120.7(3) . . ?
C12 C11 H11 119.6 . . ?
C10 C11 H11 119.6 . . ?
C11 C12 C13 119.6(3) . . ?
C11 C12 H12 120.2 . . ?
C13 C12 H12 120.2 . . ?
C12 C13 C8 119.3(3) . . ?
C12 C13 C14 131.5(3) . . ?
C8 C13 C14 109.1(2) . . ?
C22 C14 C13 113.0(2) . . ?
C22 C14 C26 113.1(2) . . ?
C13 C14 C26 110.6(2) . . ?
C22 C14 C15 109.2(2) . . ?
C13 C14 C15 100.6(2) . . ?
C26 C14 C15 109.6(2) . . ?
O1 C15 N1 124.8(3) . . ?
O1 C15 C14 126.4(3) . . ?
N1 C15 C14 108.8(2) . . ?
N2 C16 C17 131.0(3) . . ?
N2 C16 C21 107.7(3) . . ?
C17 C16 C21 121.3(3) . . ?
C18 C17 C16 117.5(4) . . ?
C18 C17 H17 121.3 . . ?
C16 C17 H17 121.3 . . ?
C17 C18 C19 122.3(4) . . ?
C17 C18 H18 118.9 . . ?
C19 C18 H18 118.9 . . ?
C20 C19 C18 120.6(4) . . ?
C20 C19 H19 119.7 . . ?
C18 C19 H19 119.7 . . ?
C19 C20 C21 119.4(3) . . ?
C19 C20 H20 120.3 . . ?
C21 C20 H20 120.3 . . ?
C20 C21 C16 118.9(3) . . ?
C20 C21 C22 135.1(3) . . ?
C16 C21 C22 106.0(3) . . ?
C23 C22 C21 106.9(3) . . ?
C23 C22 C14 127.6(3) . . ?
C21 C22 C14 125.1(2) . . ?
C22 C23 N2 110.0(3) . . ?
C22 C23 H23 125.0 . . ?
N2 C23 H23 125.0 . . ?
C25 C24 C29 120.8(3) . . ?
C25 C24 H24 119.6 . . ?
C29 C24 H24 119.6 . . ?
C24 C25 C26 121.8(3) . . ?
C24 C25 H25 119.1 . . ?
C26 C25 H25 119.1 . . ?
C27 C26 C25 116.7(3) . . ?
C27 C26 C14 123.2(3) . . ?
C25 C26 C14 120.1(3) . . ?
C28 C27 C26 121.7(3) . . ?
C28 C27 H27 119.2 . . ?
C26 C27 H27 119.2 . . ?
C27 C28 C29 120.6(3) . . ?
C27 C28 H28 119.7 . . ?
C29 C28 H28 119.7 . . ?
C28 C29 C24 118.4(3) . . ?
C28 C29 N3 119.0(3) . . ?
C24 C29 N3 122.5(3) . . ?
N3 C30 C33 123.6(4) . . ?
N3 C30 C31 119.6(3) . . ?
C33 C30 C31 116.4(4) . . ?
O2 C31 O3 124.2(4) . . ?
O2 C31 C30 124.0(4) . . ?
O3 C31 C30 111.7(4) . . ?
O3 C32 H32A 109.5 . . ?
O3 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
O3 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C30 C33 C34 124.1(4) . . ?
C30 C33 H33 118.0 . . ?
C34 C33 H33 118.0 . . ?
O4 C34 O5 121.6(4) . . ?
O4 C34 C33 124.9(4) . . ?
O5 C34 C33 113.5(4) . . ?
O5 C35 H35A 109.5 . . ?
O5 C35 H35B 109.5 . . ?
H35A C35 H35B 109.5 . . ?
O5 C35 H35C 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?
C15 N1 C8 111.0(2) . . ?
C15 N1 C7 125.0(2) . . ?
C8 N1 C7 123.9(2) . . ?
C16 N2 C23 109.3(3) . . ?
C16 N2 H2A 125.3 . . ?
C23 N2 H2A 125.3 . . ?
C30 N3 C29 126.9(3) . . ?
C30 N3 H3A 116.6 . . ?
C29 N3 H3A 116.6 . . ?
C31 O3 C32 116.1(4) . . ?
C34 O5 C35 117.2(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
N2 H2A O1 0.86 2.16 2.998(3) 164.3 2
N3 H3A O4 0.86 2.16 2.731(4) 123.3 .

_refine_diff_density_max         0.235
_refine_diff_density_min         -0.286
_refine_diff_density_rms         0.056


####################################################################### 
# 
# 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_6a
_database_code_depnum_ccdc_archive 'CCDC 2296941'
loop_
_audit_author_name
_audit_author_address
'Chao-Guo Yan' 'Yangzhou University'
_audit_update_record             
;
2023-09-23 deposited with the CCDC.	2023-11-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C36 H29 N3 O5'
_chemical_formula_sum            'C36 H29 N3 O5'
_chemical_formula_weight         583.62

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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'

_cell_length_a                   9.0882(5)
_cell_length_b                   15.9008(8)
_cell_length_c                   10.1768(5)
_cell_angle_alpha                90
_cell_angle_beta                 96.1407(17)
_cell_angle_gamma                90
_cell_volume                     1462.21(13)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    6331
_cell_measurement_theta_min      2.25
_cell_measurement_theta_max      24.97

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.326
_exptl_crystal_F_000             612
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.089
_shelx_estimated_absorpt_T_min   0.977
_shelx_estimated_absorpt_T_max   0.982
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6812
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13885
_diffrn_reflns_av_unetI/netI     0.0462
_diffrn_reflns_av_R_equivalents  0.0323
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.254
_diffrn_reflns_theta_max         25.997
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_point_group_measured_fraction_full 0.976
_reflns_number_total             5593
_reflns_number_gt                4273
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.879
_reflns_Friedel_fraction_max     0.945
_reflns_Friedel_fraction_full    0.954

_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0468P)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_abs_structure_details 
; 
 Flack x determined using 1646 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.3(5)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         5593
_refine_ls_number_parameters     399
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0651
_refine_ls_R_factor_gt           0.0400
_refine_ls_wR_factor_ref         0.0879
_refine_ls_wR_factor_gt          0.0789
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.025
_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
C1 C 0.7172(4) 0.5780(2) 1.1774(3) 0.0601(9) Uani 1 1 d . . . . .
H1 H 0.7735 0.5766 1.1063 0.072 Uiso 1 1 calc R U . . .
C2 C 0.6939(4) 0.5042(3) 1.2453(4) 0.0751(11) Uani 1 1 d . . . . .
H2 H 0.7342 0.4538 1.2196 0.090 Uiso 1 1 calc R U . . .
C3 C 0.6114(5) 0.5060(3) 1.3498(4) 0.0792(13) Uani 1 1 d . . . . .
H3 H 0.5966 0.4569 1.3962 0.095 Uiso 1 1 calc R U . . .
C4 C 0.5506(4) 0.5799(4) 1.3866(4) 0.0790(12) Uani 1 1 d . . . . .
H4 H 0.4931 0.5805 1.4569 0.095 Uiso 1 1 calc R U . . .
C5 C 0.5741(4) 0.6540(3) 1.3197(3) 0.0652(10) Uani 1 1 d . . . . .
H5 H 0.5333 0.7042 1.3458 0.078 Uiso 1 1 calc R U . . .
C6 C 0.6584(3) 0.6531(2) 1.2138(3) 0.0482(8) Uani 1 1 d . . . . .
C7 C 0.6902(4) 0.7335(2) 1.1438(3) 0.0516(8) Uani 1 1 d . . . . .
H7A H 0.6286 0.7778 1.1738 0.062 Uiso 1 1 calc R U . . .
H7B H 0.7926 0.7490 1.1683 0.062 Uiso 1 1 calc R U . . .
C8 C 0.5233(3) 0.72852(17) 0.9259(3) 0.0379(6) Uani 1 1 d . . . . .
C9 C 0.3864(3) 0.7329(2) 0.9725(3) 0.0536(8) Uani 1 1 d . . . . .
H9 H 0.3771 0.7343 1.0626 0.064 Uiso 1 1 calc R U . . .
C10 C 0.2637(3) 0.7351(2) 0.8800(4) 0.0663(10) Uani 1 1 d . . . . .
H10 H 0.1700 0.7384 0.9084 0.080 Uiso 1 1 calc R U . . .
C11 C 0.2772(3) 0.7326(2) 0.7472(4) 0.0689(10) Uani 1 1 d . . . . .
H11 H 0.1929 0.7348 0.6868 0.083 Uiso 1 1 calc R U . . .
C12 C 0.4169(3) 0.7267(2) 0.7019(3) 0.0547(8) Uani 1 1 d . . . . .
H12 H 0.4264 0.7239 0.6119 0.066 Uiso 1 1 calc R U . . .
C13 C 0.5387(3) 0.72519(17) 0.7927(3) 0.0370(6) Uani 1 1 d . . . . .
C14 C 0.7010(2) 0.71830(17) 0.7729(2) 0.0326(6) Uani 1 1 d . . . . .
C15 C 0.7741(3) 0.72195(17) 0.9203(3) 0.0361(6) Uani 1 1 d . . . . .
C16 C 0.7762(3) 0.49959(17) 0.6664(3) 0.0364(6) Uani 1 1 d . . . . .
C17 C 0.7622(3) 0.41301(19) 0.6698(3) 0.0486(8) Uani 1 1 d . . . . .
H17 H 0.8124 0.3785 0.6157 0.058 Uiso 1 1 calc R U . . .
C18 C 0.6719(4) 0.3801(2) 0.7557(3) 0.0564(9) Uani 1 1 d . . . . .
H18 H 0.6601 0.3221 0.7598 0.068 Uiso 1 1 calc R U . . .
C19 C 0.5971(3) 0.4313(2) 0.8369(3) 0.0526(8) Uani 1 1 d . . . . .
H19 H 0.5372 0.4066 0.8949 0.063 Uiso 1 1 calc R U . . .
C20 C 0.6093(3) 0.5173(2) 0.8339(3) 0.0421(7) Uani 1 1 d . . . . .
H20 H 0.5580 0.5509 0.8883 0.051 Uiso 1 1 calc R U . . .
C21 C 0.7009(3) 0.55325(17) 0.7468(3) 0.0345(6) Uani 1 1 d . . . . .
C22 C 0.7416(3) 0.63698(17) 0.7134(2) 0.0329(6) Uani 1 1 d . . . . .
C23 C 0.8364(3) 0.63161(17) 0.6185(2) 0.0322(6) Uani 1 1 d . . . . .
C24 C 0.7136(4) 0.9737(2) 0.9194(3) 0.0527(8) Uani 1 1 d . . . . .
H24 H 0.6121 0.9811 0.8998 0.063 Uiso 1 1 calc R U . . .
C25 C 0.7894(5) 1.0204(2) 1.0187(3) 0.0699(10) Uani 1 1 d . . . . .
H25 H 0.7391 1.0600 1.0641 0.084 Uiso 1 1 calc R U . . .
C26 C 0.9364(5) 1.0091(2) 1.0506(3) 0.0662(10) Uani 1 1 d . . . . .
H26 H 0.9869 1.0410 1.1175 0.079 Uiso 1 1 calc R U . . .
C27 C 1.0106(4) 0.9507(2) 0.9844(3) 0.0610(9) Uani 1 1 d . . . . .
H27 H 1.1110 0.9417 1.0082 0.073 Uiso 1 1 calc R U . . .
C28 C 0.9366(3) 0.9046(2) 0.8819(3) 0.0491(8) Uani 1 1 d . . . . .
H28 H 0.9882 0.8661 0.8355 0.059 Uiso 1 1 calc R U . . .
C29 C 0.7871(3) 0.91586(18) 0.8488(3) 0.0385(6) Uani 1 1 d . . . . .
C30 C 0.7013(3) 0.87340(17) 0.7324(3) 0.0393(7) Uani 1 1 d . . . . .
H30A H 0.5992 0.8683 0.7510 0.047 Uiso 1 1 calc R U . . .
H30B H 0.7023 0.9101 0.6564 0.047 Uiso 1 1 calc R U . . .
C31 C 0.8391(3) 0.78023(17) 0.5959(3) 0.0340(6) Uani 1 1 d . . . . .
C32 C 0.8729(3) 0.86059(19) 0.5257(3) 0.0400(7) Uani 1 1 d . . . . .
C33 C 0.7871(5) 0.9484(3) 0.3488(4) 0.1035(17) Uani 1 1 d . . . . .
H33A H 0.8000 0.9967 0.4054 0.155 Uiso 1 1 calc R U . . .
H33B H 0.7016 0.9562 0.2860 0.155 Uiso 1 1 calc R U . . .
H33C H 0.8731 0.9413 0.3027 0.155 Uiso 1 1 calc R U . . .
C34 C 0.8893(3) 0.70441(18) 0.5541(3) 0.0352(6) Uani 1 1 d . . . . .
C35 C 0.9778(3) 0.7027(2) 0.4429(3) 0.0432(7) Uani 1 1 d . . . . .
C36 C 1.1060(4) 0.6174(3) 0.3033(4) 0.0767(12) Uani 1 1 d . . . . .
H36A H 1.0566 0.6474 0.2296 0.115 Uiso 1 1 calc R U . . .
H36B H 1.1140 0.5591 0.2805 0.115 Uiso 1 1 calc R U . . .
H36C H 1.2032 0.6404 0.3252 0.115 Uiso 1 1 calc R U . . .
N1 N 0.6640(2) 0.72791(15) 1.0004(2) 0.0407(6) Uani 1 1 d . . . . .
N2 N 0.8592(2) 0.54861(14) 0.5909(2) 0.0384(6) Uani 1 1 d . . . . .
H2A H 0.9162 0.5301 0.5352 0.046 Uiso 1 1 calc R U . . .
N3 N 0.7524(2) 0.79015(14) 0.6957(2) 0.0359(6) Uani 1 1 d . . . . .
O1 O 0.9048(2) 0.71670(14) 0.95594(19) 0.0500(5) Uani 1 1 d . . . . .
O2 O 0.9734(2) 0.90698(13) 0.55916(19) 0.0479(5) Uani 1 1 d . . . . .
O3 O 0.7670(2) 0.87431(15) 0.4278(2) 0.0616(6) Uani 1 1 d . . . . .
O4 O 1.0089(3) 0.76298(14) 0.3796(2) 0.0714(7) Uani 1 1 d . . . . .
O5 O 1.0222(2) 0.62511(14) 0.4156(2) 0.0569(6) 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
C1 C6 1.375(5) . ?
C1 C2 1.389(5) . ?
C1 H1 0.9300 . ?
C2 C3 1.366(6) . ?
C2 H2 0.9300 . ?
C3 C4 1.366(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.390(6) . ?
C4 H4 0.9300 . ?
C5 C6 1.387(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.506(4) . ?
C7 N1 1.456(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C13 1.379(4) . ?
C8 C9 1.380(4) . ?
C8 N1 1.415(3) . ?
C9 C10 1.380(5) . ?
C9 H9 0.9300 . ?
C10 C11 1.371(5) . ?
C10 H10 0.9300 . ?
C11 C12 1.399(5) . ?
C11 H11 0.9300 . ?
C12 C13 1.365(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.514(3) . ?
C14 N3 1.490(3) . ?
C14 C22 1.491(4) . ?
C14 C15 1.575(4) . ?
C15 O1 1.208(3) . ?
C15 N1 1.359(3) . ?
C16 N2 1.375(3) . ?
C16 C17 1.383(4) . ?
C16 C21 1.409(4) . ?
C17 C18 1.366(4) . ?
C17 H17 0.9300 . ?
C18 C19 1.388(4) . ?
C18 H18 0.9300 . ?
C19 C20 1.374(5) . ?
C19 H19 0.9300 . ?
C20 C21 1.401(4) . ?
C20 H20 0.9300 . ?
C21 C22 1.432(4) . ?
C22 C23 1.364(4) . ?
C23 N2 1.370(3) . ?
C23 C34 1.438(4) . ?
C24 C25 1.378(5) . ?
C24 C29 1.382(4) . ?
C24 H24 0.9300 . ?
C25 C26 1.352(5) . ?
C25 H25 0.9300 . ?
C26 C27 1.367(5) . ?
C26 H26 0.9300 . ?
C27 C28 1.388(5) . ?
C27 H27 0.9300 . ?
C28 C29 1.376(4) . ?
C28 H28 0.9300 . ?
C29 C30 1.506(4) . ?
C30 N3 1.464(4) . ?
C30 H30A 0.9700 . ?
C30 H30B 0.9700 . ?
C31 N3 1.360(3) . ?
C31 C34 1.373(4) . ?
C31 C32 1.511(4) . ?
C32 O2 1.195(3) . ?
C32 O3 1.327(3) . ?
C33 O3 1.448(4) . ?
C33 H33A 0.9600 . ?
C33 H33B 0.9600 . ?
C33 H33C 0.9600 . ?
C34 C35 1.457(4) . ?
C35 O4 1.205(3) . ?
C35 O5 1.336(4) . ?
C36 O5 1.445(4) . ?
C36 H36A 0.9600 . ?
C36 H36B 0.9600 . ?
C36 H36C 0.9600 . ?
N2 H2A 0.8600 . ?

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
C6 C1 C2 121.0(3) . . ?
C6 C1 H1 119.5 . . ?
C2 C1 H1 119.5 . . ?
C3 C2 C1 119.7(4) . . ?
C3 C2 H2 120.2 . . ?
C1 C2 H2 120.2 . . ?
C2 C3 C4 120.2(4) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 H3 119.9 . . ?
C3 C4 C5 120.5(4) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C6 C5 C4 119.9(4) . . ?
C6 C5 H5 120.1 . . ?
C4 C5 H5 120.1 . . ?
C1 C6 C5 118.8(3) . . ?
C1 C6 C7 120.6(3) . . ?
C5 C6 C7 120.5(3) . . ?
N1 C7 C6 113.8(3) . . ?
N1 C7 H7A 108.8 . . ?
C6 C7 H7A 108.8 . . ?
N1 C7 H7B 108.8 . . ?
C6 C7 H7B 108.8 . . ?
H7A C7 H7B 107.7 . . ?
C13 C8 C9 122.0(3) . . ?
C13 C8 N1 110.2(2) . . ?
C9 C8 N1 127.8(3) . . ?
C8 C9 C10 117.4(3) . . ?
C8 C9 H9 121.3 . . ?
C10 C9 H9 121.3 . . ?
C11 C10 C9 121.4(3) . . ?
C11 C10 H10 119.3 . . ?
C9 C10 H10 119.3 . . ?
C10 C11 C12 120.5(3) . . ?
C10 C11 H11 119.8 . . ?
C12 C11 H11 119.8 . . ?
C13 C12 C11 118.5(3) . . ?
C13 C12 H12 120.8 . . ?
C11 C12 H12 120.8 . . ?
C12 C13 C8 120.3(2) . . ?
C12 C13 C14 130.0(3) . . ?
C8 C13 C14 109.6(2) . . ?
N3 C14 C22 110.22(19) . . ?
N3 C14 C13 112.3(2) . . ?
C22 C14 C13 113.8(2) . . ?
N3 C14 C15 110.5(2) . . ?
C22 C14 C15 108.8(2) . . ?
C13 C14 C15 100.8(2) . . ?
O1 C15 N1 126.1(2) . . ?
O1 C15 C14 125.7(2) . . ?
N1 C15 C14 108.1(2) . . ?
N2 C16 C17 129.5(3) . . ?
N2 C16 C21 108.1(2) . . ?
C17 C16 C21 122.4(3) . . ?
C18 C17 C16 117.4(3) . . ?
C18 C17 H17 121.3 . . ?
C16 C17 H17 121.3 . . ?
C17 C18 C19 121.5(3) . . ?
C17 C18 H18 119.2 . . ?
C19 C18 H18 119.2 . . ?
C20 C19 C18 121.6(3) . . ?
C20 C19 H19 119.2 . . ?
C18 C19 H19 119.2 . . ?
C19 C20 C21 118.4(3) . . ?
C19 C20 H20 120.8 . . ?
C21 C20 H20 120.8 . . ?
C20 C21 C16 118.6(3) . . ?
C20 C21 C22 135.7(3) . . ?
C16 C21 C22 105.7(2) . . ?
C23 C22 C21 108.0(2) . . ?
C23 C22 C14 123.0(2) . . ?
C21 C22 C14 128.9(2) . . ?
C22 C23 N2 109.0(2) . . ?
C22 C23 C34 122.7(2) . . ?
N2 C23 C34 128.1(2) . . ?
C25 C24 C29 120.5(3) . . ?
C25 C24 H24 119.7 . . ?
C29 C24 H24 119.7 . . ?
C26 C25 C24 120.6(3) . . ?
C26 C25 H25 119.7 . . ?
C24 C25 H25 119.7 . . ?
C25 C26 C27 119.9(3) . . ?
C25 C26 H26 120.1 . . ?
C27 C26 H26 120.1 . . ?
C26 C27 C28 120.3(3) . . ?
C26 C27 H27 119.9 . . ?
C28 C27 H27 119.9 . . ?
C29 C28 C27 120.1(3) . . ?
C29 C28 H28 119.9 . . ?
C27 C28 H28 119.9 . . ?
C28 C29 C24 118.6(3) . . ?
C28 C29 C30 123.3(3) . . ?
C24 C29 C30 117.9(3) . . ?
N3 C30 C29 117.0(2) . . ?
N3 C30 H30A 108.0 . . ?
C29 C30 H30A 108.0 . . ?
N3 C30 H30B 108.0 . . ?
C29 C30 H30B 108.0 . . ?
H30A C30 H30B 107.3 . . ?
N3 C31 C34 124.9(2) . . ?
N3 C31 C32 114.7(2) . . ?
C34 C31 C32 120.4(2) . . ?
O2 C32 O3 125.7(3) . . ?
O2 C32 C31 125.1(3) . . ?
O3 C32 C31 109.0(2) . . ?
O3 C33 H33A 109.5 . . ?
O3 C33 H33B 109.5 . . ?
H33A C33 H33B 109.5 . . ?
O3 C33 H33C 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
C31 C34 C23 115.3(2) . . ?
C31 C34 C35 119.1(2) . . ?
C23 C34 C35 125.3(3) . . ?
O4 C35 O5 122.0(3) . . ?
O4 C35 C34 125.5(3) . . ?
O5 C35 C34 112.5(3) . . ?
O5 C36 H36A 109.5 . . ?
O5 C36 H36B 109.5 . . ?
H36A C36 H36B 109.5 . . ?
O5 C36 H36C 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
C15 N1 C8 111.1(2) . . ?
C15 N1 C7 123.6(2) . . ?
C8 N1 C7 125.3(2) . . ?
C23 N2 C16 109.1(2) . . ?
C23 N2 H2A 125.4 . . ?
C16 N2 H2A 125.4 . . ?
C31 N3 C30 121.3(2) . . ?
C31 N3 C14 123.0(2) . . ?
C30 N3 C14 115.6(2) . . ?
C32 O3 C33 115.2(3) . . ?
C35 O5 C36 116.1(3) . . ?

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
N2 H2A O2 0.86 2.44 3.196(3) 146.6 2_746
N2 H2A O5 0.86 2.22 2.724(3) 117.1 .

_refine_diff_density_max         0.126
_refine_diff_density_min         -0.171
_refine_diff_density_rms         0.034

####################################################################### 
# 
# 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_7d
_database_code_depnum_ccdc_archive 'CCDC 2296942'
loop_
_audit_author_name
_audit_author_address
'Chao-Guo Yan' 'Yangzhou University'
_audit_update_record             
;
2023-09-23 deposited with the CCDC.	2023-11-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C29 H21 F N2 O6'
_chemical_formula_sum            'C29 H21 F N2 O6'
_chemical_formula_weight         512.48

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'
F F 0.0171 0.0103 '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                   23.664(3)
_cell_length_b                   10.3466(11)
_cell_length_c                   22.561(3)
_cell_angle_alpha                90
_cell_angle_beta                 116.638(3)
_cell_angle_gamma                90
_cell_volume                     4937.4(10)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2427
_cell_measurement_theta_min      2.59
_cell_measurement_theta_max      20.58

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.379
_exptl_crystal_F_000             2128
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    0.102
_shelx_estimated_absorpt_T_min   0.974
_shelx_estimated_absorpt_T_max   0.982
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6851
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            22876
_diffrn_reflns_av_unetI/netI     0.1762
_diffrn_reflns_av_R_equivalents  0.1483
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         2.587
_diffrn_reflns_theta_max         25.996
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             4830
_reflns_number_gt                2012
_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0418P)²+1.1959P] 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         4830
_refine_ls_number_parameters     345
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2219
_refine_ls_R_factor_gt           0.0687
_refine_ls_wR_factor_ref         0.1340
_refine_ls_wR_factor_gt          0.0984
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_restrained_S_all      1.006
_refine_ls_shift/su_max          0.001
_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
C1 C -0.09372(19) 0.8852(4) 0.9423(2) 0.0656(11) Uani 1 1 d . . . . .
H1 H -0.1103 0.8450 0.9679 0.079 Uiso 1 1 calc R U . . .
C2 C -0.1279(2) 0.9817(4) 0.8983(3) 0.0827(14) Uani 1 1 d . . . . .
H2 H -0.1672 1.0060 0.8944 0.099 Uiso 1 1 calc R U . . .
C3 C -0.1039(2) 1.0406(4) 0.8610(2) 0.0820(14) Uani 1 1 d . . . . .
H3 H -0.1265 1.1060 0.8316 0.098 Uiso 1 1 calc R U . . .
C4 C -0.0466(2) 1.0037(4) 0.86657(19) 0.0715(12) Uani 1 1 d . . . . .
H4 H -0.0305 1.0434 0.8403 0.086 Uiso 1 1 calc R U . . .
C5 C -0.01189(17) 0.9087(3) 0.91032(17) 0.0553(10) Uani 1 1 d . . . . .
H5 H 0.0275 0.8857 0.9140 0.066 Uiso 1 1 calc R U . . .
C6 C -0.03527(16) 0.8477(3) 0.94857(16) 0.0424(9) Uani 1 1 d . . . . .
C7 C 0.00232(15) 0.7459(3) 0.99818(15) 0.0500(9) Uani 1 1 d . . . . .
H7A H 0.0332 0.7880 1.0379 0.060 Uiso 1 1 calc R U . . .
H7B H -0.0259 0.6970 1.0103 0.060 Uiso 1 1 calc R U . . .
C8 C 0.00513(15) 0.5647(3) 0.92363(15) 0.0373(8) Uani 1 1 d . . . . .
C9 C -0.05859(16) 0.5427(3) 0.88782(16) 0.0491(9) Uani 1 1 d . . . . .
H9 H -0.0881 0.5895 0.8956 0.059 Uiso 1 1 calc R U . . .
C10 C -0.07674(17) 0.4479(4) 0.83970(17) 0.0587(10) Uani 1 1 d . . . . .
H10 H -0.1194 0.4299 0.8141 0.070 Uiso 1 1 calc R U . . .
C11 C -0.0325(2) 0.3812(3) 0.82964(16) 0.0537(10) Uani 1 1 d . . . . .
C12 C 0.03165(17) 0.4013(3) 0.86552(16) 0.0488(9) Uani 1 1 d . . . . .
H12 H 0.0610 0.3546 0.8574 0.059 Uiso 1 1 calc R U . . .
C13 C 0.04955(15) 0.4944(3) 0.91394(15) 0.0367(8) Uani 1 1 d . . . . .
C14 C 0.11452(14) 0.5423(3) 0.96078(15) 0.0379(8) Uani 1 1 d . . . . .
C15 C 0.09855(16) 0.6494(3) 0.99945(15) 0.0386(8) Uani 1 1 d . . . . .
C16 C 0.20328(16) 0.6794(3) 0.87433(16) 0.0416(9) Uani 1 1 d . . . . .
C17 C 0.20976(18) 0.7394(3) 0.82253(18) 0.0605(10) Uani 1 1 d . . . . .
H17 H 0.2493 0.7620 0.8263 0.073 Uiso 1 1 calc R U . . .
C18 C 0.1557(2) 0.7639(4) 0.76593(18) 0.0699(12) Uani 1 1 d . . . . .
H18 H 0.1587 0.8022 0.7301 0.084 Uiso 1 1 calc R U . . .
C19 C 0.09636(19) 0.7330(3) 0.76051(17) 0.0631(11) Uani 1 1 d . . . . .
H19 H 0.0605 0.7518 0.7214 0.076 Uiso 1 1 calc R U . . .
C20 C 0.08991(15) 0.6754(3) 0.81166(16) 0.0490(9) Uani 1 1 d . . . . .
H20 H 0.0500 0.6554 0.8074 0.059 Uiso 1 1 calc R U . . .
C21 C 0.14361(15) 0.6469(3) 0.87016(15) 0.0364(8) Uani 1 1 d . . . . .
C22 C 0.15597(15) 0.5864(3) 0.93141(15) 0.0364(8) Uani 1 1 d . . . . .
C23 C 0.21989(16) 0.5823(3) 0.96913(15) 0.0391(8) Uani 1 1 d . . . . .
C24 C 0.24954(15) 0.5164(3) 1.03216(15) 0.0413(9) Uani 1 1 d . . . . .
C25 C 0.31866(17) 0.5183(3) 1.07189(18) 0.0490(10) Uani 1 1 d . . . . .
C26 C 0.40526(15) 0.4582(4) 1.17150(17) 0.0796(13) Uani 1 1 d . . . . .
H26A H 0.4221 0.4007 1.1500 0.119 Uiso 1 1 calc R U . . .
H26B H 0.4142 0.4246 1.2145 0.119 Uiso 1 1 calc R U . . .
H26C H 0.4244 0.5418 1.1763 0.119 Uiso 1 1 calc R U . . .
C27 C 0.21050(16) 0.4468(3) 1.04806(15) 0.0437(9) Uani 1 1 d . . . . .
C28 C 0.22837(17) 0.3622(4) 1.1086(2) 0.0578(10) Uani 1 1 d . . . . .
C29 C 0.2833(2) 0.1765(4) 1.1642(2) 0.1100(17) Uani 1 1 d . . . . .
H29A H 0.3162 0.2239 1.1994 0.165 Uiso 1 1 calc R U . . .
H29B H 0.3006 0.0986 1.1558 0.165 Uiso 1 1 calc R U . . .
H29C H 0.2507 0.1550 1.1768 0.165 Uiso 1 1 calc R U . . .
F1 F -0.05190(10) 0.28907(19) 0.78054(10) 0.0828(7) Uani 1 1 d . . . . .
N1 N 0.03490(12) 0.6570(2) 0.97431(12) 0.0404(7) Uani 1 1 d . . . . .
N2 N 0.24886(12) 0.6392(2) 0.93533(13) 0.0466(7) Uani 1 1 d . . . . .
H2A H 0.2890 0.6483 0.9498 0.056 Uiso 1 1 calc R U . . .
O1 O 0.13717(11) 0.7135(2) 1.04477(11) 0.0538(7) Uani 1 1 d . . . . .
O2 O 0.14648(10) 0.43919(18) 1.01015(10) 0.0477(6) Uani 1 1 d . . . . .
O3 O 0.35382(12) 0.5608(3) 1.05160(12) 0.0787(9) Uani 1 1 d . . . . .
O4 O 0.33790(11) 0.4693(2) 1.13210(12) 0.0632(7) Uani 1 1 d . . . . .
O5 O 0.21650(14) 0.3913(3) 1.15255(14) 0.1007(11) Uani 1 1 d . . . . .
O6 O 0.25674(12) 0.2555(2) 1.10438(12) 0.0723(8) 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
C1 C6 1.381(4) . ?
C1 C2 1.384(5) . ?
C1 H1 0.9300 . ?
C2 C3 1.354(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.360(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.374(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.370(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.504(4) . ?
C7 N1 1.450(4) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.373(4) . ?
C8 C13 1.374(4) . ?
C8 N1 1.412(3) . ?
C9 C10 1.381(4) . ?
C9 H9 0.9300 . ?
C10 C11 1.356(5) . ?
C10 H10 0.9300 . ?
C11 F1 1.375(4) . ?
C11 C12 1.379(4) . ?
C12 C13 1.373(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.506(4) . ?
C14 C22 1.480(4) . ?
C14 O2 1.482(3) . ?
C14 C15 1.558(4) . ?
C15 O1 1.218(3) . ?
C15 N1 1.353(4) . ?
C16 N2 1.378(4) . ?
C16 C17 1.391(4) . ?
C16 C21 1.413(4) . ?
C17 C18 1.366(4) . ?
C17 H17 0.9300 . ?
C18 C19 1.391(5) . ?
C18 H18 0.9300 . ?
C19 C20 1.367(4) . ?
C19 H19 0.9300 . ?
C20 C21 1.393(4) . ?
C20 H20 0.9300 . ?
C21 C22 1.423(4) . ?
C22 C23 1.364(4) . ?
C23 N2 1.366(4) . ?
C23 C24 1.444(4) . ?
C24 C27 1.341(4) . ?
C24 C25 1.471(4) . ?
C25 O3 1.198(4) . ?
C25 O4 1.325(4) . ?
C26 O4 1.440(4) . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
C27 O2 1.368(3) . ?
C27 C28 1.513(5) . ?
C28 O5 1.185(4) . ?
C28 O6 1.317(4) . ?
C29 O6 1.458(4) . ?
C29 H29A 0.9600 . ?
C29 H29B 0.9600 . ?
C29 H29C 0.9600 . ?
N2 H2A 0.8600 . ?

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
C6 C1 C2 120.8(4) . . ?
C6 C1 H1 119.6 . . ?
C2 C1 H1 119.6 . . ?
C3 C2 C1 119.8(4) . . ?
C3 C2 H2 120.1 . . ?
C1 C2 H2 120.1 . . ?
C2 C3 C4 119.7(4) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 H3 120.2 . . ?
C3 C4 C5 121.2(4) . . ?
C3 C4 H4 119.4 . . ?
C5 C4 H4 119.4 . . ?
C6 C5 C4 120.2(4) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
C5 C6 C1 118.3(3) . . ?
C5 C6 C7 121.4(3) . . ?
C1 C6 C7 120.3(4) . . ?
N1 C7 C6 113.8(3) . . ?
N1 C7 H7A 108.8 . . ?
C6 C7 H7A 108.8 . . ?
N1 C7 H7B 108.8 . . ?
C6 C7 H7B 108.8 . . ?
H7A C7 H7B 107.7 . . ?
C9 C8 C13 122.4(3) . . ?
C9 C8 N1 127.3(3) . . ?
C13 C8 N1 110.3(3) . . ?
C8 C9 C10 116.9(3) . . ?
C8 C9 H9 121.5 . . ?
C10 C9 H9 121.5 . . ?
C11 C10 C9 120.1(3) . . ?
C11 C10 H10 119.9 . . ?
C9 C10 H10 119.9 . . ?
C10 C11 F1 118.9(3) . . ?
C10 C11 C12 123.7(3) . . ?
F1 C11 C12 117.4(4) . . ?
C13 C12 C11 116.0(3) . . ?
C13 C12 H12 122.0 . . ?
C11 C12 H12 122.0 . . ?
C12 C13 C8 120.9(3) . . ?
C12 C13 C14 130.0(3) . . ?
C8 C13 C14 109.1(3) . . ?
C22 C14 O2 109.9(2) . . ?
C22 C14 C13 117.4(3) . . ?
O2 C14 C13 107.9(2) . . ?
C22 C14 C15 114.0(3) . . ?
O2 C14 C15 105.2(2) . . ?
C13 C14 C15 101.5(3) . . ?
O1 C15 N1 126.6(3) . . ?
O1 C15 C14 125.4(3) . . ?
N1 C15 C14 108.1(3) . . ?
N2 C16 C17 129.9(3) . . ?
N2 C16 C21 107.8(3) . . ?
C17 C16 C21 122.2(3) . . ?
C18 C17 C16 117.3(3) . . ?
C18 C17 H17 121.4 . . ?
C16 C17 H17 121.4 . . ?
C17 C18 C19 121.7(3) . . ?
C17 C18 H18 119.2 . . ?
C19 C18 H18 119.2 . . ?
C20 C19 C18 121.1(3) . . ?
C20 C19 H19 119.5 . . ?
C18 C19 H19 119.5 . . ?
C19 C20 C21 119.5(3) . . ?
C19 C20 H20 120.3 . . ?
C21 C20 H20 120.3 . . ?
C20 C21 C16 118.2(3) . . ?
C20 C21 C22 135.7(3) . . ?
C16 C21 C22 106.0(3) . . ?
C23 C22 C21 107.9(3) . . ?
C23 C22 C14 118.9(3) . . ?
C21 C22 C14 132.9(3) . . ?
C22 C23 N2 109.4(3) . . ?
C22 C23 C24 122.8(3) . . ?
N2 C23 C24 127.5(3) . . ?
C27 C24 C23 115.4(3) . . ?
C27 C24 C25 123.7(3) . . ?
C23 C24 C25 120.7(3) . . ?
O3 C25 O4 123.6(3) . . ?
O3 C25 C24 123.0(3) . . ?
O4 C25 C24 113.4(3) . . ?
O4 C26 H26A 109.5 . . ?
O4 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
O4 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C24 C27 O2 124.5(3) . . ?
C24 C27 C28 127.2(3) . . ?
O2 C27 C28 108.3(3) . . ?
O5 C28 O6 126.3(4) . . ?
O5 C28 C27 122.3(4) . . ?
O6 C28 C27 111.4(4) . . ?
O6 C29 H29A 109.5 . . ?
O6 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
O6 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C15 N1 C8 111.0(3) . . ?
C15 N1 C7 123.9(3) . . ?
C8 N1 C7 125.1(3) . . ?
C23 N2 C16 108.9(3) . . ?
C23 N2 H2A 125.6 . . ?
C16 N2 H2A 125.6 . . ?
C27 O2 C14 118.5(2) . . ?
C25 O4 C26 116.1(3) . . ?
C28 O6 C29 115.2(3) . . ?

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
N2 H2A O1 0.86 2.22 2.952(3) 143.2 7_567
N2 H2A O3 0.86 2.30 2.805(3) 117.6 .

_refine_diff_density_max         0.175
_refine_diff_density_min         -0.202
_refine_diff_density_rms         0.042

