# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_3i
_database_code_depnum_ccdc_archive 'CCDC 2189810'
loop_
_audit_author_name
_audit_author_address
'Chao-Guo Yan' 'Yangzhou University'
_audit_update_record             
;
2022-07-12 deposited with the CCDC.	2022-08-23 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         'C32 H29 N3 O5'
_chemical_formula_sum            'C32 H29 N3 O5'
_chemical_formula_weight         535.58

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                   12.7017(18)
_cell_length_b                   20.368(3)
_cell_length_c                   10.6831(15)
_cell_angle_alpha                90
_cell_angle_beta                 91.573(5)
_cell_angle_gamma                90
_cell_volume                     2762.8(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9894
_cell_measurement_theta_min      2.56
_cell_measurement_theta_max      27.30

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.288
_exptl_crystal_F_000             1128
_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    0.088
_shelx_estimated_absorpt_T_min   0.979
_shelx_estimated_absorpt_T_max   0.983
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6871
_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            27432
_diffrn_reflns_av_unetI/netI     0.0381
_diffrn_reflns_av_R_equivalents  0.0410
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.153
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             5405
_reflns_number_gt                3634
_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)+(0.0592P)²+0.7539P] 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         5405
_refine_ls_number_parameters     365
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0850
_refine_ls_R_factor_gt           0.0491
_refine_ls_wR_factor_ref         0.1304
_refine_ls_wR_factor_gt          0.1139
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_restrained_S_all      1.020
_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 0.14367(16) -0.12768(10) 0.58604(19) 0.0527(5) Uani 1 1 d . . . . .
H1 H 0.0836 -0.1058 0.5568 0.063 Uiso 1 1 calc R U . . .
C2 C 0.13383(18) -0.18325(10) 0.6584(2) 0.0603(6) Uani 1 1 d . . . . .
H2 H 0.0670 -0.1978 0.6787 0.072 Uiso 1 1 calc R U . . .
C3 C 0.2207(2) -0.21746(10) 0.7012(2) 0.0644(6) Uani 1 1 d . . . . .
C4 C 0.2111(3) -0.27746(13) 0.7833(3) 0.1052(10) Uani 1 1 d . . . . .
H4A H 0.1700 -0.2669 0.8547 0.158 Uiso 1 1 calc R U . . .
H4B H 0.2800 -0.2915 0.8110 0.158 Uiso 1 1 calc R U . . .
H4C H 0.1772 -0.3121 0.7365 0.158 Uiso 1 1 calc R U . . .
C5 C 0.31803(19) -0.19457(12) 0.6672(2) 0.0704(7) Uani 1 1 d . . . . .
H5 H 0.3779 -0.2179 0.6922 0.085 Uiso 1 1 calc R U . . .
C6 C 0.32959(16) -0.13837(11) 0.5977(2) 0.0595(6) Uani 1 1 d . . . . .
H6 H 0.3964 -0.1234 0.5786 0.071 Uiso 1 1 calc R U . . .
C7 C 0.24178(15) -0.10439(9) 0.55666(17) 0.0448(4) Uani 1 1 d . . . . .
C8 C 0.14945(15) 0.03172(10) 0.62128(19) 0.0514(5) Uani 1 1 d . . . . .
C9 C 0.20189(14) 0.01076(9) 0.50219(17) 0.0430(4) Uani 1 1 d . . . . .
C10 C 0.19740(13) 0.06140(8) 0.42144(16) 0.0393(4) Uani 1 1 d . . . . .
C11 C 0.14467(14) 0.11599(9) 0.48044(18) 0.0437(4) Uani 1 1 d . . . . .
C12 C 0.0630(2) 0.13490(12) 0.6906(2) 0.0745(7) Uani 1 1 d . . . . .
H12A H -0.0024 0.1151 0.7130 0.112 Uiso 1 1 calc R U . . .
H12B H 0.0498 0.1777 0.6558 0.112 Uiso 1 1 calc R U . . .
H12C H 0.1082 0.1389 0.7637 0.112 Uiso 1 1 calc R U . . .
C13 C 0.31870(15) -0.04689(9) 0.37275(18) 0.0493(5) Uani 1 1 d . . . . .
H13A H 0.3343 -0.0919 0.3499 0.059 Uiso 1 1 calc R U . . .
H13B H 0.3848 -0.0249 0.3929 0.059 Uiso 1 1 calc R U . . .
C14 C 0.26384(14) -0.01226(8) 0.26171(17) 0.0414(4) Uani 1 1 d . . . . .
H14 H 0.1960 -0.0343 0.2473 0.050 Uiso 1 1 calc R U . . .
C15 C 0.32476(15) -0.01979(10) 0.14298(19) 0.0481(5) Uani 1 1 d . . . . .
C16 C 0.3951(2) -0.09727(13) 0.0039(3) 0.0888(8) Uani 1 1 d . . . . .
H16A H 0.3573 -0.0789 -0.0669 0.133 Uiso 1 1 calc R U . . .
H16B H 0.4004 -0.1440 -0.0061 0.133 Uiso 1 1 calc R U . . .
H16C H 0.4644 -0.0786 0.0095 0.133 Uiso 1 1 calc R U . . .
C17 C 0.33436(19) 0.29284(11) 0.3019(2) 0.0645(6) Uani 1 1 d . . . . .
H17 H 0.3061 0.2621 0.3559 0.077 Uiso 1 1 calc R U . . .
C18 C 0.3287(2) 0.35925(12) 0.3309(2) 0.0746(7) Uani 1 1 d . . . . .
H18 H 0.2971 0.3726 0.4042 0.090 Uiso 1 1 calc R U . . .
C19 C 0.36938(19) 0.40510(11) 0.2521(2) 0.0678(6) Uani 1 1 d . . . . .
H19 H 0.3673 0.4494 0.2727 0.081 Uiso 1 1 calc R U . . .
C20 C 0.41321(18) 0.38533(11) 0.1427(2) 0.0675(6) Uani 1 1 d . . . . .
H20 H 0.4390 0.4163 0.0874 0.081 Uiso 1 1 calc R U . . .
C21 C 0.41908(17) 0.31918(11) 0.1143(2) 0.0628(6) Uani 1 1 d . . . . .
H21 H 0.4490 0.3061 0.0399 0.075 Uiso 1 1 calc R U . . .
C22 C 0.38115(15) 0.27221(9) 0.19478(18) 0.0484(5) Uani 1 1 d . . . . .
C23 C 0.39541(15) 0.20065(9) 0.1642(2) 0.0538(5) Uani 1 1 d . . . . .
H23A H 0.3976 0.1961 0.0739 0.065 Uiso 1 1 calc R U . . .
H23B H 0.4632 0.1866 0.1986 0.065 Uiso 1 1 calc R U . . .
C24 C 0.33895(15) 0.10394(9) 0.28380(18) 0.0439(5) Uani 1 1 d . . . . .
C25 C 0.23920(13) 0.06043(8) 0.29136(16) 0.0378(4) Uani 1 1 d . . . . .
C26 C 0.16557(13) 0.09390(8) 0.19806(16) 0.0378(4) Uani 1 1 d . . . . .
C27 C 0.06544(14) 0.07795(9) 0.15809(17) 0.0443(5) Uani 1 1 d . . . . .
H27 H 0.0339 0.0398 0.1867 0.053 Uiso 1 1 calc R U . . .
C28 C 0.01070(15) 0.11912(10) 0.07428(18) 0.0510(5) Uani 1 1 d . . . . .
C29 C -0.09918(18) 0.10217(13) 0.0288(2) 0.0751(7) Uani 1 1 d . . . . .
H29A H -0.1255 0.1363 -0.0255 0.113 Uiso 1 1 calc R U . . .
H29B H -0.1441 0.0979 0.0992 0.113 Uiso 1 1 calc R U . . .
H29C H -0.0980 0.0614 -0.0163 0.113 Uiso 1 1 calc R U . . .
C30 C 0.06022(16) 0.17622(10) 0.03559(19) 0.0543(5) Uani 1 1 d . . . . .
H30 H 0.0241 0.2042 -0.0193 0.065 Uiso 1 1 calc R U . . .
C31 C 0.16113(16) 0.19304(10) 0.07561(18) 0.0510(5) Uani 1 1 d . . . . .
H31 H 0.1928 0.2315 0.0488 0.061 Uiso 1 1 calc R U . . .
C32 C 0.21279(14) 0.15089(8) 0.15614(17) 0.0408(4) Uani 1 1 d . . . . .
N1 N 0.25254(12) -0.04655(7) 0.48275(15) 0.0501(4) Uani 1 1 d . . . . .
N2 N 0.11383(13) 0.09415(8) 0.59860(15) 0.0527(4) Uani 1 1 d . . . . .
N3 N 0.31506(12) 0.15673(7) 0.20984(14) 0.0447(4) Uani 1 1 d . . . . .
O1 O 0.14102(13) 0.00174(8) 0.71783(14) 0.0716(4) Uani 1 1 d . . . . .
O2 O 0.12659(11) 0.17079(7) 0.44109(13) 0.0593(4) Uani 1 1 d . . . . .
O3 O 0.35425(14) 0.02403(8) 0.07934(16) 0.0792(5) Uani 1 1 d . . . . .
O4 O 0.33961(12) -0.08271(7) 0.11698(14) 0.0658(4) Uani 1 1 d . . . . .
O5 O 0.42334(11) 0.09342(7) 0.33627(14) 0.0606(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 C7 1.378(3) . ?
C1 C2 1.379(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.372(3) . ?
C2 H2 0.9300 . ?
C3 C5 1.380(3) . ?
C3 C4 1.511(3) . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C5 C6 1.374(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.374(3) . ?
C6 H6 0.9300 . ?
C7 N1 1.427(2) . ?
C8 O1 1.206(2) . ?
C8 N2 1.369(3) . ?
C8 C9 1.514(3) . ?
C9 C10 1.345(2) . ?
C9 N1 1.352(2) . ?
C10 C11 1.451(2) . ?
C10 C25 1.501(2) . ?
C11 O2 1.212(2) . ?
C11 N2 1.404(2) . ?
C12 N2 1.451(2) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 N1 1.463(2) . ?
C13 C14 1.531(3) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C15 1.512(3) . ?
C14 C25 1.548(2) . ?
C14 H14 0.9800 . ?
C15 O3 1.189(2) . ?
C15 O4 1.326(2) . ?
C16 O4 1.446(3) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 C22 1.370(3) . ?
C17 C18 1.390(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.368(3) . ?
C18 H18 0.9300 . ?
C19 C20 1.369(3) . ?
C19 H19 0.9300 . ?
C20 C21 1.383(3) . ?
C20 H20 0.9300 . ?
C21 C22 1.382(3) . ?
C21 H21 0.9300 . ?
C22 C23 1.506(3) . ?
C23 N3 1.452(2) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C24 O5 1.215(2) . ?
C24 N3 1.364(2) . ?
C24 C25 1.550(2) . ?
C25 C26 1.511(2) . ?
C26 C27 1.369(2) . ?
C26 C32 1.387(2) . ?
C27 C28 1.398(3) . ?
C27 H27 0.9300 . ?
C28 C30 1.390(3) . ?
C28 C29 1.505(3) . ?
C29 H29A 0.9600 . ?
C29 H29B 0.9600 . ?
C29 H29C 0.9600 . ?
C30 C31 1.383(3) . ?
C30 H30 0.9300 . ?
C31 C32 1.370(3) . ?
C31 H31 0.9300 . ?
C32 N3 1.411(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 C1 C2 120.46(19) . . ?
C7 C1 H1 119.8 . . ?
C2 C1 H1 119.8 . . ?
C3 C2 C1 121.3(2) . . ?
C3 C2 H2 119.4 . . ?
C1 C2 H2 119.4 . . ?
C2 C3 C5 117.33(19) . . ?
C2 C3 C4 121.8(2) . . ?
C5 C3 C4 120.9(2) . . ?
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 122.2(2) . . ?
C6 C5 H5 118.9 . . ?
C3 C5 H5 118.9 . . ?
C7 C6 C5 119.61(19) . . ?
C7 C6 H6 120.2 . . ?
C5 C6 H6 120.2 . . ?
C6 C7 C1 119.03(18) . . ?
C6 C7 N1 120.22(17) . . ?
C1 C7 N1 120.75(17) . . ?
O1 C8 N2 125.80(19) . . ?
O1 C8 C9 128.87(19) . . ?
N2 C8 C9 105.31(16) . . ?
C10 C9 N1 125.15(16) . . ?
C10 C9 C8 108.12(16) . . ?
N1 C9 C8 126.51(17) . . ?
C9 C10 C11 108.72(16) . . ?
C9 C10 C25 125.02(15) . . ?
C11 C10 C25 126.25(16) . . ?
O2 C11 N2 123.26(17) . . ?
O2 C11 C10 129.80(18) . . ?
N2 C11 C10 106.93(16) . . ?
N2 C12 H12A 109.5 . . ?
N2 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
N2 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N1 C13 C14 111.15(14) . . ?
N1 C13 H13A 109.4 . . ?
C14 C13 H13A 109.4 . . ?
N1 C13 H13B 109.4 . . ?
C14 C13 H13B 109.4 . . ?
H13A C13 H13B 108.0 . . ?
C15 C14 C13 111.76(15) . . ?
C15 C14 C25 112.33(15) . . ?
C13 C14 C25 111.86(15) . . ?
C15 C14 H14 106.8 . . ?
C13 C14 H14 106.8 . . ?
C25 C14 H14 106.8 . . ?
O3 C15 O4 123.85(18) . . ?
O3 C15 C14 125.46(18) . . ?
O4 C15 C14 110.67(17) . . ?
O4 C16 H16A 109.5 . . ?
O4 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
O4 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C22 C17 C18 120.7(2) . . ?
C22 C17 H17 119.7 . . ?
C18 C17 H17 119.7 . . ?
C19 C18 C17 120.3(2) . . ?
C19 C18 H18 119.8 . . ?
C17 C18 H18 119.8 . . ?
C18 C19 C20 119.6(2) . . ?
C18 C19 H19 120.2 . . ?
C20 C19 H19 120.2 . . ?
C19 C20 C21 119.9(2) . . ?
C19 C20 H20 120.0 . . ?
C21 C20 H20 120.0 . . ?
C22 C21 C20 121.1(2) . . ?
C22 C21 H21 119.5 . . ?
C20 C21 H21 119.5 . . ?
C17 C22 C21 118.30(19) . . ?
C17 C22 C23 122.39(18) . . ?
C21 C22 C23 119.28(18) . . ?
N3 C23 C22 115.71(16) . . ?
N3 C23 H23A 108.4 . . ?
C22 C23 H23A 108.4 . . ?
N3 C23 H23B 108.4 . . ?
C22 C23 H23B 108.4 . . ?
H23A C23 H23B 107.4 . . ?
O5 C24 N3 125.87(17) . . ?
O5 C24 C25 125.95(17) . . ?
N3 C24 C25 108.17(15) . . ?
C10 C25 C26 112.12(14) . . ?
C10 C25 C14 106.30(14) . . ?
C26 C25 C14 114.93(14) . . ?
C10 C25 C24 110.55(14) . . ?
C26 C25 C24 101.52(14) . . ?
C14 C25 C24 111.47(14) . . ?
C27 C26 C32 120.27(17) . . ?
C27 C26 C25 130.66(16) . . ?
C32 C26 C25 108.99(15) . . ?
C26 C27 C28 119.92(17) . . ?
C26 C27 H27 120.0 . . ?
C28 C27 H27 120.0 . . ?
C30 C28 C27 118.10(18) . . ?
C30 C28 C29 121.26(19) . . ?
C27 C28 C29 120.63(19) . . ?
C28 C29 H29A 109.5 . . ?
C28 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C28 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C31 C30 C28 122.56(19) . . ?
C31 C30 H30 118.7 . . ?
C28 C30 H30 118.7 . . ?
C32 C31 C30 117.57(18) . . ?
C32 C31 H31 121.2 . . ?
C30 C31 H31 121.2 . . ?
C31 C32 C26 121.56(17) . . ?
C31 C32 N3 128.50(17) . . ?
C26 C32 N3 109.93(15) . . ?
C9 N1 C7 125.09(15) . . ?
C9 N1 C13 114.43(15) . . ?
C7 N1 C13 120.42(15) . . ?
C8 N2 C11 110.75(15) . . ?
C8 N2 C12 124.22(18) . . ?
C11 N2 C12 124.59(17) . . ?
C24 N3 C32 110.92(14) . . ?
C24 N3 C23 122.23(16) . . ?
C32 N3 C23 124.29(16) . . ?
C15 O4 C16 116.66(18) . . ?

_refine_diff_density_max         0.239
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.036


####################################################################### 
# 
# 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_3l
_database_code_depnum_ccdc_archive 'CCDC 2189813'
loop_
_audit_author_name
_audit_author_address
'Chao-Guo Yan' 'Yangzhou University'
_audit_update_record             
;
2022-07-12 deposited with the CCDC.	2022-08-23 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         'C31 H26 Cl N3 O5'
_chemical_formula_sum            'C31 H26 Cl N3 O5'
_chemical_formula_weight         556.00

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                   9.2939(12)
_cell_length_b                   11.4737(17)
_cell_length_c                   13.2237(18)
_cell_angle_alpha                78.635(5)
_cell_angle_beta                 87.607(4)
_cell_angle_gamma                75.843(4)
_cell_volume                     1340.4(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    7610
_cell_measurement_theta_min      2.56
_cell_measurement_theta_max      27.49

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.378
_exptl_crystal_F_000             580
_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    0.190
_shelx_estimated_absorpt_T_min   0.956
_shelx_estimated_absorpt_T_max   0.963
_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            19165
_diffrn_reflns_av_unetI/netI     0.0385
_diffrn_reflns_av_R_equivalents  0.0345
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.260
_diffrn_reflns_theta_max         25.998
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.996
_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             5253
_reflns_number_gt                3708
_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)+(0.0514P)²+0.5560P] 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         5253
_refine_ls_number_parameters     374
_refine_ls_number_restraints     37
_refine_ls_R_factor_all          0.0786
_refine_ls_R_factor_gt           0.0483
_refine_ls_wR_factor_ref         0.1224
_refine_ls_wR_factor_gt          0.1079
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.063
_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 1.1512(4) 0.4484(3) 0.7761(3) 0.0856(10) Uani 1 1 d . . . . .
H1 H 1.2148 0.3820 0.8168 0.103 Uiso 1 1 calc R U . . .
C2 C 1.1566(5) 0.5664(4) 0.7825(4) 0.1203(15) Uani 1 1 d . . . . .
H2 H 1.2231 0.5783 0.8278 0.144 Uiso 1 1 calc R U . . .
C3 C 1.0652(4) 0.6652(3) 0.7228(3) 0.0903(11) Uani 1 1 d . . . . .
H3 H 1.0688 0.7445 0.7265 0.108 Uiso 1 1 calc R U . . .
C4 C 0.9706(4) 0.6452(3) 0.6589(3) 0.0940(11) Uani 1 1 d . . . . .
H4 H 0.9071 0.7117 0.6182 0.113 Uiso 1 1 calc R U . . .
C5 C 0.9648(4) 0.5289(3) 0.6520(2) 0.0804(9) Uani 1 1 d . . . . .
H5 H 0.8986 0.5180 0.6058 0.096 Uiso 1 1 calc R U . . .
C6 C 1.0545(2) 0.4286(2) 0.71154(17) 0.0418(5) Uani 1 1 d . . . . .
C7 C 1.0500(2) 0.2999(2) 0.70639(18) 0.0449(5) Uani 1 1 d . . . . .
H7A H 1.0671 0.2884 0.6357 0.054 Uiso 1 1 calc R U . . .
H7B H 1.1303 0.2434 0.7484 0.054 Uiso 1 1 calc R U . . .
C8 C 0.8831(2) 0.22510(18) 0.84230(16) 0.0369(5) Uani 1 1 d . . . . .
C9 C 0.7249(2) 0.20249(17) 0.84904(14) 0.0312(4) Uani 1 1 d . . . . .
C10 C 0.6778(2) 0.23476(17) 0.73706(14) 0.0315(4) Uani 1 1 d . . . . .
C11 C 0.5472(2) 0.23383(18) 0.69256(15) 0.0366(5) Uani 1 1 d . . . . .
H11 H 0.4732 0.2049 0.7316 0.044 Uiso 1 1 calc R U . . .
C12 C 0.5301(2) 0.2775(2) 0.58759(16) 0.0444(5) Uani 1 1 d . . . . .
C13 C 0.6403(3) 0.3186(2) 0.52829(17) 0.0570(7) Uani 1 1 d . . . . .
H13 H 0.6255 0.3471 0.4577 0.068 Uiso 1 1 calc R U . . .
C14 C 0.7723(3) 0.3175(2) 0.57325(17) 0.0534(6) Uani 1 1 d . . . . .
H14 H 0.8475 0.3443 0.5339 0.064 Uiso 1 1 calc R U . . .
C15 C 0.7893(2) 0.27567(19) 0.67772(15) 0.0370(5) Uani 1 1 d . . . . .
C16 C 0.6626(3) 0.24674(18) 1.03087(15) 0.0389(5) Uani 1 1 d . . . . .
H16A H 0.7628 0.2534 1.0412 0.047 Uiso 1 1 calc R U . . .
H16B H 0.5960 0.3009 1.0695 0.047 Uiso 1 1 calc R U . . .
C17 C 0.6227(2) 0.28735(17) 0.91650(14) 0.0342(5) Uani 1 1 d . . . . .
H17 H 0.5207 0.2811 0.9085 0.041 Uiso 1 1 calc R U . . .
C18 C 0.6248(3) 0.4209(2) 0.88374(17) 0.0487(6) Uani 1 1 d . U . . .
C19 C 0.5730(4) 0.5920(2) 0.7484(2) 0.0873(10) Uani 1 1 d . U . . .
H19A H 0.4820 0.6461 0.7638 0.131 Uiso 1 1 calc R U . . .
H19B H 0.5836 0.6002 0.6749 0.131 Uiso 1 1 calc R U . . .
H19C H 0.6550 0.6126 0.7764 0.131 Uiso 1 1 calc R U . . .
C20 C 0.5731(2) 0.0879(2) 1.25036(16) 0.0427(5) Uani 1 1 d . . . . .
H20 H 0.4746 0.1141 1.2286 0.051 Uiso 1 1 calc R U . . .
C21 C 0.6077(3) 0.0574(2) 1.35452(16) 0.0504(6) Uani 1 1 d . . . . .
H21 H 0.5312 0.0637 1.4022 0.061 Uiso 1 1 calc R U . . .
C22 C 0.7529(3) 0.01796(19) 1.38962(15) 0.0419(5) Uani 1 1 d . . . . .
C23 C 0.7889(3) -0.0134(3) 1.50339(17) 0.0646(7) Uani 1 1 d . . . . .
H23A H 0.7906 0.0599 1.5275 0.097 Uiso 1 1 calc R U . . .
H23B H 0.8843 -0.0700 1.5149 0.097 Uiso 1 1 calc R U . . .
H23C H 0.7147 -0.0500 1.5402 0.097 Uiso 1 1 calc R U . . .
C24 C 0.8641(2) 0.0089(2) 1.31666(16) 0.0438(5) Uani 1 1 d . . . . .
H24 H 0.9627 -0.0185 1.3381 0.053 Uiso 1 1 calc R U . . .
C25 C 0.8309(2) 0.0398(2) 1.21255(16) 0.0419(5) Uani 1 1 d . . . . .
H25 H 0.9071 0.0339 1.1646 0.050 Uiso 1 1 calc R U . . .
C26 C 0.6859(2) 0.07906(17) 1.17942(14) 0.0316(4) Uani 1 1 d . . . . .
C27 C 0.7028(2) -0.09227(18) 1.02803(15) 0.0320(4) Uani 1 1 d . . . . .
C28 C 0.6968(2) 0.04288(17) 1.00339(14) 0.0297(4) Uani 1 1 d . . . . .
C29 C 0.7280(2) 0.07394(17) 0.90294(14) 0.0306(4) Uani 1 1 d . . . . .
C30 C 0.7673(2) -0.03769(18) 0.85975(15) 0.0337(4) Uani 1 1 d . . . . .
C31 C 0.7870(3) -0.2627(2) 0.93145(19) 0.0531(6) Uani 1 1 d . . . . .
H31A H 0.8744 -0.3048 0.9718 0.080 Uiso 1 1 calc R U . . .
H31B H 0.8052 -0.2695 0.8606 0.080 Uiso 1 1 calc R U . . .
H31C H 0.7062 -0.2986 0.9567 0.080 Uiso 1 1 calc R U . . .
Cl1 Cl 0.36398(7) 0.28203(7) 0.52849(5) 0.0682(2) Uani 1 1 d . . . . .
N1 N 0.90984(18) 0.26906(16) 0.74136(13) 0.0390(4) Uani 1 1 d . . . . .
N2 N 0.65263(18) 0.11990(14) 1.07054(12) 0.0346(4) Uani 1 1 d . . . . .
N3 N 0.74933(18) -0.13437(15) 0.93939(12) 0.0363(4) Uani 1 1 d . . . . .
O1 O 0.96902(17) 0.20622(15) 0.91347(12) 0.0537(4) Uani 1 1 d . . . . .
O2 O 0.7063(14) 0.4685(7) 0.9231(7) 0.081(2) Uani 0.553(18) 1 d . U P A 1
O2' O 0.6263(18) 0.4875(7) 0.9447(6) 0.074(2) Uani 0.447(18) 1 d . U P A 2
O3 O 0.5706(3) 0.46811(15) 0.79304(13) 0.0755(6) Uani 1 1 d . U . . .
O4 O 0.66864(16) -0.15170(13) 1.10746(11) 0.0420(4) Uani 1 1 d . . . . .
O5 O 0.80871(17) -0.05141(14) 0.77412(11) 0.0475(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 1.352(3) . ?
C1 C2 1.386(4) . ?
C1 H1 0.9300 . ?
C2 C3 1.364(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.332(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.369(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.367(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.503(3) . ?
C7 N1 1.465(2) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 O1 1.212(2) . ?
C8 N1 1.366(3) . ?
C8 C9 1.550(3) . ?
C9 C29 1.500(3) . ?
C9 C10 1.510(3) . ?
C9 C17 1.570(3) . ?
C10 C11 1.374(3) . ?
C10 C15 1.391(3) . ?
C11 C12 1.382(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.381(3) . ?
C12 Cl1 1.744(2) . ?
C13 C14 1.382(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.372(3) . ?
C14 H14 0.9300 . ?
C15 N1 1.408(3) . ?
C16 N2 1.471(2) . ?
C16 C17 1.525(3) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 C18 1.513(3) . ?
C17 H17 0.9800 . ?
C18 O2' 1.218(7) . ?
C18 O2 1.221(6) . ?
C18 O3 1.283(3) . ?
C19 O3 1.433(3) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 C26 1.376(3) . ?
C20 C21 1.384(3) . ?
C20 H20 0.9300 . ?
C21 C22 1.382(3) . ?
C21 H21 0.9300 . ?
C22 C24 1.383(3) . ?
C22 C23 1.508(3) . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C24 C25 1.381(3) . ?
C24 H24 0.9300 . ?
C25 C26 1.373(3) . ?
C25 H25 0.9300 . ?
C26 N2 1.445(2) . ?
C27 O4 1.210(2) . ?
C27 N3 1.369(3) . ?
C27 C28 1.508(3) . ?
C28 C29 1.344(3) . ?
C28 N2 1.356(2) . ?
C29 C30 1.464(3) . ?
C30 O5 1.208(2) . ?
C30 N3 1.408(2) . ?
C31 N3 1.451(3) . ?
C31 H31A 0.9600 . ?
C31 H31B 0.9600 . ?
C31 H31C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 C1 C2 120.9(3) . . ?
C6 C1 H1 119.6 . . ?
C2 C1 H1 119.6 . . ?
C3 C2 C1 120.6(3) . . ?
C3 C2 H2 119.7 . . ?
C1 C2 H2 119.7 . . ?
C4 C3 C2 118.4(3) . . ?
C4 C3 H3 120.8 . . ?
C2 C3 H3 120.8 . . ?
C3 C4 C5 121.5(3) . . ?
C3 C4 H4 119.3 . . ?
C5 C4 H4 119.3 . . ?
C6 C5 C4 121.2(3) . . ?
C6 C5 H5 119.4 . . ?
C4 C5 H5 119.4 . . ?
C1 C6 C5 117.5(2) . . ?
C1 C6 C7 119.9(2) . . ?
C5 C6 C7 122.5(2) . . ?
N1 C7 C6 113.89(18) . . ?
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 . . ?
O1 C8 N1 125.70(19) . . ?
O1 C8 C9 126.35(18) . . ?
N1 C8 C9 107.95(16) . . ?
C29 C9 C10 115.79(15) . . ?
C29 C9 C8 110.84(15) . . ?
C10 C9 C8 101.87(15) . . ?
C29 C9 C17 105.44(15) . . ?
C10 C9 C17 112.61(15) . . ?
C8 C9 C17 110.36(15) . . ?
C11 C10 C15 120.89(18) . . ?
C11 C10 C9 130.08(17) . . ?
C15 C10 C9 108.95(16) . . ?
C10 C11 C12 117.46(18) . . ?
C10 C11 H11 121.3 . . ?
C12 C11 H11 121.3 . . ?
C13 C12 C11 121.9(2) . . ?
C13 C12 Cl1 119.09(16) . . ?
C11 C12 Cl1 119.01(16) . . ?
C12 C13 C14 120.4(2) . . ?
C12 C13 H13 119.8 . . ?
C14 C13 H13 119.8 . . ?
C15 C14 C13 118.0(2) . . ?
C15 C14 H14 121.0 . . ?
C13 C14 H14 121.0 . . ?
C14 C15 C10 121.34(19) . . ?
C14 C15 N1 128.83(18) . . ?
C10 C15 N1 109.80(17) . . ?
N2 C16 C17 111.89(16) . . ?
N2 C16 H16A 109.2 . . ?
C17 C16 H16A 109.2 . . ?
N2 C16 H16B 109.2 . . ?
C17 C16 H16B 109.2 . . ?
H16A C16 H16B 107.9 . . ?
C18 C17 C16 108.56(16) . . ?
C18 C17 C9 113.32(17) . . ?
C16 C17 C9 112.13(16) . . ?
C18 C17 H17 107.5 . . ?
C16 C17 H17 107.5 . . ?
C9 C17 H17 107.5 . . ?
O2' C18 O3 119.3(4) . . ?
O2 C18 O3 120.7(4) . . ?
O2' C18 C17 123.2(4) . . ?
O2 C18 C17 123.1(4) . . ?
O3 C18 C17 112.83(19) . . ?
O3 C19 H19A 109.5 . . ?
O3 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
O3 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C26 C20 C21 119.32(19) . . ?
C26 C20 H20 120.3 . . ?
C21 C20 H20 120.3 . . ?
C22 C21 C20 121.9(2) . . ?
C22 C21 H21 119.1 . . ?
C20 C21 H21 119.1 . . ?
C21 C22 C24 117.63(19) . . ?
C21 C22 C23 121.2(2) . . ?
C24 C22 C23 121.1(2) . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C25 C24 C22 121.0(2) . . ?
C25 C24 H24 119.5 . . ?
C22 C24 H24 119.5 . . ?
C26 C25 C24 120.37(19) . . ?
C26 C25 H25 119.8 . . ?
C24 C25 H25 119.8 . . ?
C25 C26 C20 119.81(18) . . ?
C25 C26 N2 119.86(17) . . ?
C20 C26 N2 120.16(17) . . ?
O4 C27 N3 126.35(18) . . ?
O4 C27 C28 128.11(18) . . ?
N3 C27 C28 105.48(16) . . ?
C29 C28 N2 126.80(17) . . ?
C29 C28 C27 108.54(17) . . ?
N2 C28 C27 124.36(16) . . ?
C28 C29 C30 108.28(16) . . ?
C28 C29 C9 123.84(17) . . ?
C30 C29 C9 127.86(16) . . ?
O5 C30 N3 123.56(18) . . ?
O5 C30 C29 129.79(18) . . ?
N3 C30 C29 106.65(16) . . ?
N3 C31 H31A 109.5 . . ?
N3 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
N3 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C8 N1 C15 111.33(16) . . ?
C8 N1 C7 122.83(17) . . ?
C15 N1 C7 125.79(17) . . ?
C28 N2 C26 120.93(16) . . ?
C28 N2 C16 114.65(15) . . ?
C26 N2 C16 113.55(15) . . ?
C27 N3 C30 110.84(16) . . ?
C27 N3 C31 124.30(17) . . ?
C30 N3 C31 124.67(17) . . ?
C18 O3 C19 119.6(2) . . ?

_refine_diff_density_max         0.200
_refine_diff_density_min         -0.337
_refine_diff_density_rms         0.046


####################################################################### 
# 
# 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_3ii
_database_code_depnum_ccdc_archive 'CCDC 2189811'
loop_
_audit_author_name
_audit_author_address
'Chao-Guo Yan' 'Yangzhou University'
_audit_update_record             
;
2022-07-12 deposited with the CCDC.	2022-08-23 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         'C32 H29 N3 O5, C H Cl3'
_chemical_formula_sum            'C33 H30 Cl3 N3 O5'
_chemical_formula_weight         654.95

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      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                   13.0140(14)
_cell_length_b                   11.1280(11)
_cell_length_c                   21.958(3)
_cell_angle_alpha                90
_cell_angle_beta                 94.274(4)
_cell_angle_gamma                90
_cell_volume                     3171.1(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5929
_cell_measurement_theta_min      2.34
_cell_measurement_theta_max      22.42

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.372
_exptl_crystal_F_000             1360
_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    0.335
_shelx_estimated_absorpt_T_min   0.924
_shelx_estimated_absorpt_T_max   0.936
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6854
_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            27460
_diffrn_reflns_av_unetI/netI     0.0633
_diffrn_reflns_av_R_equivalents  0.0672
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         2.343
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_full        24.997
_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             5577
_reflns_number_gt                3242
_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)+(0.0998P)²+1.1164P] 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         5577
_refine_ls_number_parameters     401
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1313
_refine_ls_R_factor_gt           0.0690
_refine_ls_wR_factor_ref         0.1993
_refine_ls_wR_factor_gt          0.1786
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_restrained_S_all      1.075
_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
N3 N 0.8116(2) 0.9660(2) 1.02269(13) 0.0384(7) Uani 1 1 d . . . . .
N2 N 0.5754(2) 0.7911(2) 0.84572(12) 0.0383(7) Uani 1 1 d . . . . .
N1 N 0.7527(2) 0.5576(2) 0.89639(12) 0.0367(7) Uani 1 1 d . . . . .
O3 O 0.88220(19) 0.9373(2) 0.93066(12) 0.0507(7) Uani 1 1 d . . . . .
O1 O 0.57266(19) 0.6053(2) 0.80014(11) 0.0517(7) Uani 1 1 d . . . . .
O2 O 0.6145(2) 0.9480(2) 0.91240(11) 0.0526(7) Uani 1 1 d . . . . .
O5 O 0.96926(19) 0.7652(2) 1.05131(11) 0.0510(7) Uani 1 1 d . . . . .
O4 O 0.9318(2) 0.5713(3) 1.06285(13) 0.0667(8) Uani 1 1 d . . . . .
C10 C 0.7059(2) 0.7594(3) 0.92079(14) 0.0319(8) Uani 1 1 d . . . . .
C22 C 0.7303(2) 0.7858(3) 1.03520(14) 0.0307(8) Uani 1 1 d . . . . .
C7 C 0.7402(2) 0.4480(3) 0.86230(15) 0.0351(8) Uani 1 1 d . . . . .
C9 C 0.6964(2) 0.6577(3) 0.88638(14) 0.0310(8) Uani 1 1 d . . . . .
C21 C 0.7800(2) 0.7778(3) 0.97489(14) 0.0307(8) Uani 1 1 d . . . . .
C23 C 0.6705(3) 0.7048(3) 1.06472(16) 0.0379(8) Uani 1 1 d . . . . .
H23 H 0.6550 0.6305 1.0469 0.045 Uiso 1 1 calc R U . . .
C28 C 0.7525(2) 0.8970(3) 1.06159(15) 0.0352(8) Uani 1 1 d . . . . .
C8 C 0.6088(3) 0.6761(3) 0.83757(15) 0.0360(8) Uani 1 1 d . . . . .
C31 C 0.9244(3) 0.6614(3) 1.03356(16) 0.0404(9) Uani 1 1 d . . . . .
C27 C 0.7181(3) 0.9283(3) 1.11715(17) 0.0488(10) Uani 1 1 d . . . . .
H27 H 0.7344 1.0025 1.1347 0.059 Uiso 1 1 calc R U . . .
C30 C 0.8631(2) 0.6754(3) 0.97299(15) 0.0347(8) Uani 1 1 d . . . . .
H30 H 0.9109 0.6976 0.9424 0.042 Uiso 1 1 calc R U . . .
C18 C 0.7586(3) 1.1767(3) 1.04220(15) 0.0415(9) Uani 1 1 d . . . . .
C20 C 0.8321(3) 0.9027(3) 0.97183(16) 0.0379(8) Uani 1 1 d . . . . .
C29 C 0.8157(3) 0.5542(3) 0.95479(16) 0.0419(9) Uani 1 1 d . . . . .
H29A H 0.8706 0.4959 0.9518 0.050 Uiso 1 1 calc R U . . .
H29B H 0.7732 0.5274 0.9866 0.050 Uiso 1 1 calc R U . . .
C11 C 0.6307(3) 0.8465(3) 0.89575(15) 0.0365(8) Uani 1 1 d . . . . .
C13 C 0.6595(3) 1.1560(3) 1.01852(16) 0.0451(9) Uani 1 1 d . . . . .
H13 H 0.6442 1.0850 0.9975 0.054 Uiso 1 1 calc R U . . .
C19 C 0.8458(3) 1.0883(3) 1.03528(19) 0.0501(10) Uani 1 1 d . . . . .
H19A H 0.8859 1.1152 1.0023 0.060 Uiso 1 1 calc R U . . .
H19B H 0.8908 1.0887 1.0725 0.060 Uiso 1 1 calc R U . . .
C6 C 0.7105(3) 0.3451(3) 0.89123(17) 0.0493(10) Uani 1 1 d . . . . .
H6 H 0.6961 0.3481 0.9320 0.059 Uiso 1 1 calc R U . . .
C26 C 0.6581(3) 0.8455(4) 1.14634(17) 0.0541(11) Uani 1 1 d . . . . .
H26 H 0.6340 0.8656 1.1838 0.065 Uiso 1 1 calc R U . . .
C12 C 0.4844(3) 0.8451(4) 0.81387(17) 0.0548(10) Uani 1 1 d . . . . .
H12A H 0.5024 0.9217 0.7975 0.082 Uiso 1 1 calc R U . . .
H12B H 0.4321 0.8560 0.8419 0.082 Uiso 1 1 calc R U . . .
H12C H 0.4590 0.7933 0.7812 0.082 Uiso 1 1 calc R U . . .
C5 C 0.7023(3) 0.2382(3) 0.86001(19) 0.0557(11) Uani 1 1 d . . . . .
H5 H 0.6816 0.1699 0.8802 0.067 Uiso 1 1 calc R U . . .
C14 C 0.5824(3) 1.2386(4) 1.02539(19) 0.0567(11) Uani 1 1 d . . . . .
H14 H 0.5156 1.2232 1.0093 0.068 Uiso 1 1 calc R U . . .
C1 C 0.7634(3) 0.4416(3) 0.80243(16) 0.0445(9) Uani 1 1 d . . . . .
H1 H 0.7847 0.5100 0.7825 0.053 Uiso 1 1 calc R U . . .
C24 C 0.6334(3) 0.7334(3) 1.12083(16) 0.0473(10) Uani 1 1 d . . . . .
C2 C 0.7548(3) 0.3329(3) 0.77177(17) 0.0496(10) Uani 1 1 d . . . . .
H2 H 0.7705 0.3296 0.7312 0.060 Uiso 1 1 calc R U . . .
C3 C 0.7238(3) 0.2293(3) 0.79974(18) 0.0491(10) Uani 1 1 d . . . . .
C15 C 0.6050(4) 1.3442(4) 1.0563(2) 0.0650(12) Uani 1 1 d . . . . .
H15 H 0.5532 1.4003 1.0611 0.078 Uiso 1 1 calc R U . . .
C32 C 1.0185(4) 0.7701(4) 1.11259(19) 0.0701(13) Uani 1 1 d . . . . .
H32A H 0.9676 0.7590 1.1416 0.105 Uiso 1 1 calc R U . . .
H32B H 1.0511 0.8468 1.1192 0.105 Uiso 1 1 calc R U . . .
H32C H 1.0693 0.7076 1.1176 0.105 Uiso 1 1 calc R U . . .
C17 C 0.7793(4) 1.2836(3) 1.07305(18) 0.0568(11) Uani 1 1 d . . . . .
H17 H 0.8460 1.2992 1.0893 0.068 Uiso 1 1 calc R U . . .
C16 C 0.7035(4) 1.3670(4) 1.0801(2) 0.0657(13) Uani 1 1 d . . . . .
H16 H 0.7187 1.4383 1.1009 0.079 Uiso 1 1 calc R U . . .
C25 C 0.5682(4) 0.6466(4) 1.1531(2) 0.0750(14) Uani 1 1 d . . . . .
H25A H 0.5289 0.5983 1.1236 0.113 Uiso 1 1 calc R U . . .
H25B H 0.5222 0.6902 1.1772 0.113 Uiso 1 1 calc R U . . .
H25C H 0.6117 0.5957 1.1792 0.113 Uiso 1 1 calc R U . . .
C4 C 0.7137(4) 0.1110(4) 0.7665(2) 0.0821(15) Uani 1 1 d . . . . .
H4A H 0.6436 0.0999 0.7507 0.123 Uiso 1 1 calc R U . . .
H4B H 0.7332 0.0468 0.7943 0.123 Uiso 1 1 calc R U . . .
H4C H 0.7580 0.1107 0.7334 0.123 Uiso 1 1 calc R U . . .
C33 C 0.9158(4) 0.6736(4) 0.3012(2) 0.0759(14) Uani 1 1 d . . . . .
H33 H 0.8868 0.6483 0.3391 0.091 Uiso 1 1 calc R U . . .
Cl2 Cl 0.81383(12) 0.70500(14) 0.24809(7) 0.1047(5) Uani 1 1 d . . . . .
Cl1 Cl 0.98532(14) 0.80544(16) 0.31657(8) 0.1215(6) Uani 1 1 d . . . . .
Cl3 Cl 0.99217(14) 0.55950(16) 0.27834(10) 0.1390(7) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N3 C20 1.364(4) . ?
N3 C28 1.417(4) . ?
N3 C19 1.452(4) . ?
N2 C8 1.369(4) . ?
N2 C11 1.410(4) . ?
N2 C12 1.458(5) . ?
N1 C9 1.343(4) . ?
N1 C7 1.434(4) . ?
N1 C29 1.471(4) . ?
O3 C20 1.216(4) . ?
O1 C8 1.208(4) . ?
O2 C11 1.210(4) . ?
O5 C31 1.338(4) . ?
O5 C32 1.448(4) . ?
O4 C31 1.192(4) . ?
C10 C9 1.361(4) . ?
C10 C11 1.457(5) . ?
C10 C21 1.487(4) . ?
C22 C23 1.383(4) . ?
C22 C28 1.387(4) . ?
C22 C21 1.519(4) . ?
C7 C1 1.372(5) . ?
C7 C6 1.378(5) . ?
C9 C8 1.519(5) . ?
C21 C20 1.549(5) . ?
C21 C30 1.573(4) . ?
C23 C24 1.394(5) . ?
C23 H23 0.9300 . ?
C28 C27 1.375(5) . ?
C31 C30 1.507(5) . ?
C27 C26 1.393(5) . ?
C27 H27 0.9300 . ?
C30 C29 1.524(4) . ?
C30 H30 0.9800 . ?
C18 C13 1.373(5) . ?
C18 C17 1.386(5) . ?
C18 C19 1.518(5) . ?
C29 H29A 0.9700 . ?
C29 H29B 0.9700 . ?
C13 C14 1.377(5) . ?
C13 H13 0.9300 . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C6 C5 1.373(5) . ?
C6 H6 0.9300 . ?
C26 C24 1.395(5) . ?
C26 H26 0.9300 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C5 C3 1.377(5) . ?
C5 H5 0.9300 . ?
C14 C15 1.379(6) . ?
C14 H14 0.9300 . ?
C1 C2 1.384(5) . ?
C1 H1 0.9300 . ?
C24 C25 1.498(5) . ?
C2 C3 1.381(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.507(5) . ?
C15 C16 1.371(6) . ?
C15 H15 0.9300 . ?
C32 H32A 0.9600 . ?
C32 H32B 0.9600 . ?
C32 H32C 0.9600 . ?
C17 C16 1.371(6) . ?
C17 H17 0.9300 . ?
C16 H16 0.9300 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C33 Cl3 1.710(5) . ?
C33 Cl2 1.736(5) . ?
C33 Cl1 1.743(5) . ?
C33 H33 0.9800 . ?

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
C20 N3 C28 111.2(3) . . ?
C20 N3 C19 124.4(3) . . ?
C28 N3 C19 124.5(3) . . ?
C8 N2 C11 111.2(3) . . ?
C8 N2 C12 125.3(3) . . ?
C11 N2 C12 122.9(3) . . ?
C9 N1 C7 125.5(3) . . ?
C9 N1 C29 115.2(3) . . ?
C7 N1 C29 117.9(2) . . ?
C31 O5 C32 117.2(3) . . ?
C9 C10 C11 108.2(3) . . ?
C9 C10 C21 125.8(3) . . ?
C11 C10 C21 125.9(3) . . ?
C23 C22 C28 119.5(3) . . ?
C23 C22 C21 131.4(3) . . ?
C28 C22 C21 109.1(3) . . ?
C1 C7 C6 119.2(3) . . ?
C1 C7 N1 121.3(3) . . ?
C6 C7 N1 119.4(3) . . ?
N1 C9 C10 124.9(3) . . ?
N1 C9 C8 126.8(3) . . ?
C10 C9 C8 108.2(3) . . ?
C10 C21 C22 114.3(3) . . ?
C10 C21 C20 110.4(3) . . ?
C22 C21 C20 101.6(2) . . ?
C10 C21 C30 106.5(2) . . ?
C22 C21 C30 113.8(2) . . ?
C20 C21 C30 110.2(3) . . ?
C22 C23 C24 120.6(3) . . ?
C22 C23 H23 119.7 . . ?
C24 C23 H23 119.7 . . ?
C27 C28 C22 121.6(3) . . ?
C27 C28 N3 128.7(3) . . ?
C22 C28 N3 109.7(3) . . ?
O1 C8 N2 126.0(3) . . ?
O1 C8 C9 128.8(3) . . ?
N2 C8 C9 105.2(3) . . ?
O4 C31 O5 123.6(3) . . ?
O4 C31 C30 125.4(3) . . ?
O5 C31 C30 111.0(3) . . ?
C28 C27 C26 118.1(3) . . ?
C28 C27 H27 120.9 . . ?
C26 C27 H27 120.9 . . ?
C31 C30 C29 108.5(3) . . ?
C31 C30 C21 111.8(3) . . ?
C29 C30 C21 112.5(3) . . ?
C31 C30 H30 108.0 . . ?
C29 C30 H30 108.0 . . ?
C21 C30 H30 108.0 . . ?
C13 C18 C17 118.1(3) . . ?
C13 C18 C19 122.8(3) . . ?
C17 C18 C19 119.1(3) . . ?
O3 C20 N3 126.4(3) . . ?
O3 C20 C21 125.2(3) . . ?
N3 C20 C21 108.4(3) . . ?
N1 C29 C30 113.2(3) . . ?
N1 C29 H29A 108.9 . . ?
C30 C29 H29A 108.9 . . ?
N1 C29 H29B 108.9 . . ?
C30 C29 H29B 108.9 . . ?
H29A C29 H29B 107.7 . . ?
O2 C11 N2 123.6(3) . . ?
O2 C11 C10 129.4(3) . . ?
N2 C11 C10 107.0(3) . . ?
C18 C13 C14 121.2(4) . . ?
C18 C13 H13 119.4 . . ?
C14 C13 H13 119.4 . . ?
N3 C19 C18 113.9(3) . . ?
N3 C19 H19A 108.8 . . ?
C18 C19 H19A 108.8 . . ?
N3 C19 H19B 108.8 . . ?
C18 C19 H19B 108.8 . . ?
H19A C19 H19B 107.7 . . ?
C5 C6 C7 120.2(3) . . ?
C5 C6 H6 119.9 . . ?
C7 C6 H6 119.9 . . ?
C27 C26 C24 121.8(3) . . ?
C27 C26 H26 119.1 . . ?
C24 C26 H26 119.1 . . ?
N2 C12 H12A 109.5 . . ?
N2 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
N2 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C6 C5 C3 121.9(4) . . ?
C6 C5 H5 119.1 . . ?
C3 C5 H5 119.1 . . ?
C13 C14 C15 119.5(4) . . ?
C13 C14 H14 120.2 . . ?
C15 C14 H14 120.2 . . ?
C7 C1 C2 119.7(3) . . ?
C7 C1 H1 120.1 . . ?
C2 C1 H1 120.1 . . ?
C23 C24 C26 118.3(3) . . ?
C23 C24 C25 121.1(4) . . ?
C26 C24 C25 120.6(4) . . ?
C3 C2 C1 121.9(3) . . ?
C3 C2 H2 119.0 . . ?
C1 C2 H2 119.0 . . ?
C5 C3 C2 117.1(3) . . ?
C5 C3 C4 120.8(4) . . ?
C2 C3 C4 122.2(4) . . ?
C16 C15 C14 120.3(4) . . ?
C16 C15 H15 119.9 . . ?
C14 C15 H15 119.9 . . ?
O5 C32 H32A 109.5 . . ?
O5 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
O5 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C16 C17 C18 121.4(4) . . ?
C16 C17 H17 119.3 . . ?
C18 C17 H17 119.3 . . ?
C15 C16 C17 119.5(4) . . ?
C15 C16 H16 120.3 . . ?
C17 C16 H16 120.3 . . ?
C24 C25 H25A 109.5 . . ?
C24 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C24 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
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 . . ?
Cl3 C33 Cl2 112.6(3) . . ?
Cl3 C33 Cl1 112.2(3) . . ?
Cl2 C33 Cl1 108.7(2) . . ?
Cl3 C33 H33 107.7 . . ?
Cl2 C33 H33 107.7 . . ?
Cl1 C33 H33 107.7 . . ?

_refine_diff_density_max         0.474
_refine_diff_density_min         -0.679
_refine_diff_density_rms         0.058


####################################################################### 
# 
# 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_3kk
_database_code_depnum_ccdc_archive 'CCDC 2189812'
loop_
_audit_author_name
_audit_author_address
'Chao-Guo Yan' 'Yangzhou University'
_audit_update_record             
;
2022-07-12 deposited with the CCDC.	2022-08-23 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         'C30 H24 Cl N3 O5'
_chemical_formula_sum            'C30 H24 Cl N3 O5'
_chemical_formula_weight         541.97

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      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                   9.4166(4)
_cell_length_b                   11.3916(5)
_cell_length_c                   24.6355(11)
_cell_angle_alpha                90
_cell_angle_beta                 94.6982(15)
_cell_angle_gamma                90
_cell_volume                     2633.8(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    8744
_cell_measurement_theta_min      2.39
_cell_measurement_theta_max      25.37

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.367
_exptl_crystal_F_000             1128
_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    0.191
_shelx_estimated_absorpt_T_min   0.956
_shelx_estimated_absorpt_T_max   0.963
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6850
_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            24775
_diffrn_reflns_av_unetI/netI     0.0392
_diffrn_reflns_av_R_equivalents  0.0409
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         2.386
_diffrn_reflns_theta_max         25.997
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             5163
_reflns_number_gt                3499
_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)+(0.0430P)²+0.8997P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0270(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         5163
_refine_ls_number_parameters     355
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0808
_refine_ls_R_factor_gt           0.0435
_refine_ls_wR_factor_ref         0.1101
_refine_ls_wR_factor_gt          0.0942
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_restrained_S_all      1.019
_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 0.7871(2) 0.36844(18) 0.07000(9) 0.0574(6) Uani 1 1 d . . . . .
H1 H 0.8333 0.3465 0.1033 0.069 Uiso 1 1 calc R U . . .
C2 C 0.8413(3) 0.4563(2) 0.04027(12) 0.0715(7) Uani 1 1 d . . . . .
H2 H 0.9242 0.4947 0.0535 0.086 Uiso 1 1 calc R U . . .
C3 C 0.7757(4) 0.4879(2) -0.00808(12) 0.0794(8) Uani 1 1 d . . . . .
H3 H 0.8138 0.5478 -0.0280 0.095 Uiso 1 1 calc R U . . .
C4 C 0.6542(4) 0.4328(3) -0.02814(10) 0.0827(8) Uani 1 1 d . . . . .
H4 H 0.6097 0.4551 -0.0616 0.099 Uiso 1 1 calc R U . . .
C5 C 0.5966(3) 0.3428(2) 0.00160(9) 0.0631(6) Uani 1 1 d . . . . .
H5 H 0.5139 0.3043 -0.0118 0.076 Uiso 1 1 calc R U . . .
C6 C 0.6641(2) 0.31245(17) 0.05072(8) 0.0432(5) Uani 1 1 d . . . . .
C7 C 0.5231(2) 0.33802(17) 0.15822(8) 0.0434(5) Uani 1 1 d . . . . .
C8 C 0.5604(2) 0.22522(16) 0.13022(7) 0.0405(5) Uani 1 1 d . . . . .
C9 C 0.52837(19) 0.13390(16) 0.16188(7) 0.0389(4) Uani 1 1 d . . . . .
C10 C 0.4750(2) 0.18034(17) 0.21137(8) 0.0433(5) Uani 1 1 d . . . . .
C11 C 0.4323(2) 0.38370(18) 0.24825(9) 0.0563(6) Uani 1 1 d . . . . .
H11A H 0.4867 0.3684 0.2822 0.085 Uiso 1 1 calc R U . . .
H11B H 0.3329 0.3726 0.2526 0.085 Uiso 1 1 calc R U . . .
H11C H 0.4484 0.4631 0.2372 0.085 Uiso 1 1 calc R U . . .
C12 C 0.4327(2) -0.13698(19) 0.31569(9) 0.0542(6) Uani 1 1 d . . . . .
H12 H 0.4388 -0.0676 0.2961 0.065 Uiso 1 1 calc R U . . .
C13 C 0.3505(2) -0.1412(2) 0.35922(9) 0.0622(6) Uani 1 1 d . . . . .
H13 H 0.3001 -0.0750 0.3686 0.075 Uiso 1 1 calc R U . . .
C14 C 0.3422(3) -0.2422(2) 0.38892(10) 0.0708(7) Uani 1 1 d . . . . .
H14 H 0.2873 -0.2445 0.4186 0.085 Uiso 1 1 calc R U . . .
C15 C 0.4156(3) -0.3403(2) 0.37453(10) 0.0694(7) Uani 1 1 d . . . . .
H15 H 0.4112 -0.4089 0.3948 0.083 Uiso 1 1 calc R U . . .
C16 C 0.4953(2) -0.33723(18) 0.33028(9) 0.0540(5) Uani 1 1 d . . . . .
H16 H 0.5422 -0.4046 0.3201 0.065 Uiso 1 1 calc R U . . .
C17 C 0.5064(2) -0.23508(17) 0.30073(8) 0.0448(5) Uani 1 1 d . . . . .
C18 C 0.6021(2) -0.2330(2) 0.25463(9) 0.0590(6) Uani 1 1 d . . . . .
H18A H 0.6982 -0.2139 0.2692 0.071 Uiso 1 1 calc R U . . .
H18B H 0.6043 -0.3109 0.2388 0.071 Uiso 1 1 calc R U . . .
C19 C 0.6337(2) -0.05128(17) 0.20156(8) 0.0446(5) Uani 1 1 d . . . . .
C20 C 0.56170(19) 0.00831(16) 0.14995(7) 0.0384(4) Uani 1 1 d . . . . .
C21 C 0.43450(19) -0.07157(15) 0.13680(7) 0.0370(4) Uani 1 1 d . . . . .
C22 C 0.32447(19) -0.06567(17) 0.09620(8) 0.0423(5) Uani 1 1 d . . . . .
H22 H 0.3188 -0.0045 0.0711 0.051 Uiso 1 1 calc R U . . .
C23 C 0.2230(2) -0.15363(18) 0.09410(8) 0.0485(5) Uani 1 1 d . . . . .
C24 C 0.2295(2) -0.24477(18) 0.13073(9) 0.0565(6) Uani 1 1 d . . . . .
H24 H 0.1598 -0.3028 0.1280 0.068 Uiso 1 1 calc R U . . .
C25 C 0.3392(2) -0.25072(18) 0.17162(9) 0.0534(5) Uani 1 1 d . . . . .
H25 H 0.3445 -0.3120 0.1967 0.064 Uiso 1 1 calc R U . . .
C26 C 0.4400(2) -0.16340(16) 0.17405(7) 0.0408(5) Uani 1 1 d . . . . .
C27 C 0.6229(2) 0.09749(17) 0.05952(8) 0.0510(5) Uani 1 1 d . . . . .
H27A H 0.6922 0.0966 0.0325 0.061 Uiso 1 1 calc R U . . .
H27B H 0.5317 0.0733 0.0419 0.061 Uiso 1 1 calc R U . . .
C28 C 0.6684(2) 0.01165(17) 0.10487(8) 0.0437(5) Uani 1 1 d . . . . .
H28 H 0.7598 0.0394 0.1220 0.052 Uiso 1 1 calc R U . . .
C29 C 0.6939(2) -0.10844(19) 0.08139(10) 0.0503(5) Uani 1 1 d . . . . .
C30 C 0.7659(3) -0.3022(2) 0.10569(13) 0.0914(9) Uani 1 1 d . . . . .
H30A H 0.6755 -0.3405 0.0982 0.137 Uiso 1 1 calc R U . . .
H30B H 0.8193 -0.3417 0.1351 0.137 Uiso 1 1 calc R U . . .
H30C H 0.8179 -0.3047 0.0738 0.137 Uiso 1 1 calc R U . . .
Cl1 Cl 0.08153(6) -0.14665(6) 0.04374(3) 0.0760(2) Uani 1 1 d . . . . .
N1 N 0.61087(19) 0.21663(14) 0.08087(6) 0.0498(4) Uani 1 1 d . . . . .
N2 N 0.47635(17) 0.30346(14) 0.20701(6) 0.0454(4) Uani 1 1 d . . . . .
N3 N 0.55822(17) -0.14955(14) 0.21198(6) 0.0451(4) Uani 1 1 d . . . . .
O1 O 0.52938(17) 0.43728(12) 0.14194(6) 0.0596(4) Uani 1 1 d . . . . .
O2 O 0.43593(17) 0.12870(12) 0.25052(6) 0.0617(4) Uani 1 1 d . . . . .
O3 O 0.74062(15) -0.01666(14) 0.22758(6) 0.0614(4) Uani 1 1 d . . . . .
O4 O 0.67424(18) -0.13428(14) 0.03435(7) 0.0721(5) Uani 1 1 d . . . . .
O5 O 0.74308(18) -0.18134(14) 0.12064(7) 0.0689(5) 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 C2 1.364(3) . ?
C1 C6 1.372(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.345(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.362(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.396(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.365(3) . ?
C5 H5 0.9300 . ?
C6 N1 1.434(2) . ?
C7 O1 1.203(2) . ?
C7 N2 1.371(2) . ?
C7 C8 1.513(3) . ?
C8 N1 1.345(2) . ?
C8 C9 1.349(2) . ?
C9 C10 1.456(3) . ?
C9 C20 1.499(3) . ?
C10 O2 1.212(2) . ?
C10 N2 1.407(2) . ?
C11 N2 1.452(2) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 C13 1.374(3) . ?
C12 C17 1.381(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.369(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.375(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.374(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.381(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.507(3) . ?
C18 N3 1.451(2) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 O3 1.214(2) . ?
C19 N3 1.362(2) . ?
C19 C20 1.548(3) . ?
C20 C21 1.518(2) . ?
C20 C28 1.558(3) . ?
C21 C22 1.382(2) . ?
C21 C26 1.390(3) . ?
C22 C23 1.383(3) . ?
C22 H22 0.9300 . ?
C23 C24 1.374(3) . ?
C23 Cl1 1.746(2) . ?
C24 C25 1.384(3) . ?
C24 H24 0.9300 . ?
C25 C26 1.372(3) . ?
C25 H25 0.9300 . ?
C26 N3 1.403(2) . ?
C27 N1 1.463(2) . ?
C27 C28 1.520(3) . ?
C27 H27A 0.9700 . ?
C27 H27B 0.9700 . ?
C28 C29 1.512(3) . ?
C28 H28 0.9800 . ?
C29 O4 1.195(2) . ?
C29 O5 1.329(3) . ?
C30 O5 1.446(3) . ?
C30 H30A 0.9600 . ?
C30 H30B 0.9600 . ?
C30 H30C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 119.8(2) . . ?
C2 C1 H1 120.1 . . ?
C6 C1 H1 120.1 . . ?
C3 C2 C1 120.5(3) . . ?
C3 C2 H2 119.8 . . ?
C1 C2 H2 119.8 . . ?
C2 C3 C4 120.6(2) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 H3 119.7 . . ?
C3 C4 C5 120.0(2) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C6 C5 C4 118.6(2) . . ?
C6 C5 H5 120.7 . . ?
C4 C5 H5 120.7 . . ?
C5 C6 C1 120.5(2) . . ?
C5 C6 N1 119.65(19) . . ?
C1 C6 N1 119.70(18) . . ?
O1 C7 N2 126.20(18) . . ?
O1 C7 C8 128.79(18) . . ?
N2 C7 C8 105.01(16) . . ?
N1 C8 C9 125.37(17) . . ?
N1 C8 C7 125.91(16) . . ?
C9 C8 C7 108.66(16) . . ?
C8 C9 C10 108.23(16) . . ?
C8 C9 C20 124.22(17) . . ?
C10 C9 C20 127.11(16) . . ?
O2 C10 N2 123.35(18) . . ?
O2 C10 C9 129.64(18) . . ?
N2 C10 C9 107.00(16) . . ?
N2 C11 H11A 109.5 . . ?
N2 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
N2 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C13 C12 C17 120.5(2) . . ?
C13 C12 H12 119.8 . . ?
C17 C12 H12 119.8 . . ?
C14 C13 C12 120.4(2) . . ?
C14 C13 H13 119.8 . . ?
C12 C13 H13 119.8 . . ?
C13 C14 C15 119.6(2) . . ?
C13 C14 H14 120.2 . . ?
C15 C14 H14 120.2 . . ?
C16 C15 C14 120.2(2) . . ?
C16 C15 H15 119.9 . . ?
C14 C15 H15 119.9 . . ?
C15 C16 C17 120.6(2) . . ?
C15 C16 H16 119.7 . . ?
C17 C16 H16 119.7 . . ?
C16 C17 C12 118.66(19) . . ?
C16 C17 C18 119.11(19) . . ?
C12 C17 C18 122.19(18) . . ?
N3 C18 C17 113.81(16) . . ?
N3 C18 H18A 108.8 . . ?
C17 C18 H18A 108.8 . . ?
N3 C18 H18B 108.8 . . ?
C17 C18 H18B 108.8 . . ?
H18A C18 H18B 107.7 . . ?
O3 C19 N3 126.19(18) . . ?
O3 C19 C20 125.42(18) . . ?
N3 C19 C20 108.38(16) . . ?
C9 C20 C21 116.09(15) . . ?
C9 C20 C19 110.01(15) . . ?
C21 C20 C19 101.38(15) . . ?
C9 C20 C28 105.91(15) . . ?
C21 C20 C28 113.97(15) . . ?
C19 C20 C28 109.37(15) . . ?
C22 C21 C26 119.98(17) . . ?
C22 C21 C20 131.09(17) . . ?
C26 C21 C20 108.92(15) . . ?
C21 C22 C23 117.84(18) . . ?
C21 C22 H22 121.1 . . ?
C23 C22 H22 121.1 . . ?
C24 C23 C22 121.97(19) . . ?
C24 C23 Cl1 119.46(16) . . ?
C22 C23 Cl1 118.57(17) . . ?
C23 C24 C25 120.38(19) . . ?
C23 C24 H24 119.8 . . ?
C25 C24 H24 119.8 . . ?
C26 C25 C24 117.92(19) . . ?
C26 C25 H25 121.0 . . ?
C24 C25 H25 121.0 . . ?
C25 C26 C21 121.91(18) . . ?
C25 C26 N3 128.23(18) . . ?
C21 C26 N3 109.86(16) . . ?
N1 C27 C28 110.97(15) . . ?
N1 C27 H27A 109.4 . . ?
C28 C27 H27A 109.4 . . ?
N1 C27 H27B 109.4 . . ?
C28 C27 H27B 109.4 . . ?
H27A C27 H27B 108.0 . . ?
C29 C28 C27 110.18(16) . . ?
C29 C28 C20 112.49(16) . . ?
C27 C28 C20 112.35(16) . . ?
C29 C28 H28 107.2 . . ?
C27 C28 H28 107.2 . . ?
C20 C28 H28 107.2 . . ?
O4 C29 O5 124.7(2) . . ?
O4 C29 C28 125.2(2) . . ?
O5 C29 C28 110.11(18) . . ?
O5 C30 H30A 109.5 . . ?
O5 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
O5 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C8 N1 C6 125.27(16) . . ?
C8 N1 C27 115.85(15) . . ?
C6 N1 C27 118.64(15) . . ?
C7 N2 C10 111.03(16) . . ?
C7 N2 C11 124.27(16) . . ?
C10 N2 C11 124.70(16) . . ?
C19 N3 C26 111.41(15) . . ?
C19 N3 C18 123.56(17) . . ?
C26 N3 C18 124.88(17) . . ?
C29 O5 C30 117.38(19) . . ?

_refine_diff_density_max         0.208
_refine_diff_density_min         -0.188
_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_4cc
_database_code_depnum_ccdc_archive 'CCDC 2189814'
loop_
_audit_author_name
_audit_author_address
'Chao-Guo Yan' 'Yangzhou University'
_audit_update_record             
;
2022-07-12 deposited with the CCDC.	2022-08-23 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 Cl N4 O3'
_chemical_formula_sum            'C29 H21 Cl N4 O3'
_chemical_formula_weight         508.95

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      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                   18.3989(11)
_cell_length_b                   11.1620(7)
_cell_length_c                   12.1197(7)
_cell_angle_alpha                90
_cell_angle_beta                 95.609(2)
_cell_angle_gamma                90
_cell_volume                     2477.1(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5215
_cell_measurement_theta_min      2.22
_cell_measurement_theta_max      24.34

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.365
_exptl_crystal_F_000             1056
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.260
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.194
_shelx_estimated_absorpt_T_min   0.948
_shelx_estimated_absorpt_T_max   0.962
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6653
_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            22796
_diffrn_reflns_av_unetI/netI     0.0670
_diffrn_reflns_av_R_equivalents  0.0656
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.112
_diffrn_reflns_theta_max         25.999
_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             4857
_reflns_number_gt                2813
_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)+(0.0442P)²+0.7191P] 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         4857
_refine_ls_number_parameters     335
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1168
_refine_ls_R_factor_gt           0.0511
_refine_ls_wR_factor_ref         0.1164
_refine_ls_wR_factor_gt          0.0954
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_restrained_S_all      1.013
_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 0.86679(15) 0.0508(2) 0.2939(2) 0.0572(7) Uani 1 1 d . . . . .
H1 H 0.8170 0.0352 0.2807 0.069 Uiso 1 1 calc R U . . .
C2 C 0.9144(2) -0.0401(3) 0.3285(2) 0.0752(9) Uani 1 1 d . . . . .
H2 H 0.8969 -0.1172 0.3376 0.090 Uiso 1 1 calc R U . . .
C3 C 0.9871(2) -0.0166(4) 0.3495(3) 0.0856(11) Uani 1 1 d . . . . .
H3 H 1.0191 -0.0773 0.3752 0.103 Uiso 1 1 calc R U . . .
C4 C 1.01321(16) 0.0964(4) 0.3328(3) 0.0814(10) Uani 1 1 d . . . . .
H4 H 1.0630 0.1116 0.3464 0.098 Uiso 1 1 calc R U . . .
C5 C 0.96670(13) 0.1868(3) 0.2964(2) 0.0587(7) Uani 1 1 d . . . . .
H5 H 0.9848 0.2629 0.2837 0.070 Uiso 1 1 calc R U . . .
C6 C 0.89288(12) 0.1643(2) 0.27885(19) 0.0434(6) Uani 1 1 d . . . . .
C7 C 0.87934(12) 0.4063(2) 0.3992(2) 0.0453(6) Uani 1 1 d . . . . .
C8 C 0.84213(11) 0.3682(2) 0.28772(18) 0.0356(5) Uani 1 1 d . . . . .
C9 C 0.80344(11) 0.4629(2) 0.24449(17) 0.0335(5) Uani 1 1 d . . . . .
C10 C 0.81891(12) 0.5655(2) 0.31649(19) 0.0409(6) Uani 1 1 d . . . . .
C11 C 0.89269(16) 0.6011(3) 0.5006(2) 0.0757(9) Uani 1 1 d . . . . .
H11A H 0.9020 0.5528 0.5660 0.114 Uiso 1 1 calc R U . . .
H11B H 0.8572 0.6614 0.5130 0.114 Uiso 1 1 calc R U . . .
H11C H 0.9372 0.6387 0.4839 0.114 Uiso 1 1 calc R U . . .
C12 C 0.68760(13) 0.8628(2) 0.1347(2) 0.0534(7) Uani 1 1 d . . . . .
H12 H 0.7171 0.8077 0.1755 0.064 Uiso 1 1 calc R U . . .
C13 C 0.66665(15) 0.9657(3) 0.1849(3) 0.0656(8) Uani 1 1 d . . . . .
H13 H 0.6816 0.9794 0.2594 0.079 Uiso 1 1 calc R U . . .
C14 C 0.62398(18) 1.0482(3) 0.1260(3) 0.0810(10) Uani 1 1 d . . . . .
H14 H 0.6099 1.1179 0.1601 0.097 Uiso 1 1 calc R U . . .
C15 C 0.6022(2) 1.0274(3) 0.0169(4) 0.0992(12) Uani 1 1 d . . . . .
H15 H 0.5735 1.0839 -0.0236 0.119 Uiso 1 1 calc R U . . .
C16 C 0.62228(17) 0.9233(3) -0.0344(3) 0.0783(9) Uani 1 1 d . . . . .
H16 H 0.6066 0.9097 -0.1086 0.094 Uiso 1 1 calc R U . . .
C17 C 0.66551(13) 0.8399(2) 0.0246(2) 0.0450(6) Uani 1 1 d . . . . .
C18 C 0.68673(13) 0.7276(2) -0.03291(19) 0.0476(6) Uani 1 1 d . . . . .
H18A H 0.6484 0.7078 -0.0907 0.057 Uiso 1 1 calc R U . . .
H18B H 0.7309 0.7432 -0.0682 0.057 Uiso 1 1 calc R U . . .
C19 C 0.76554(12) 0.5727(2) 0.06515(18) 0.0377(6) Uani 1 1 d . . . . .
C20 C 0.75556(11) 0.46121(19) 0.13764(17) 0.0335(5) Uani 1 1 d . . . . .
C21 C 0.67409(11) 0.46557(19) 0.14910(17) 0.0313(5) Uani 1 1 d . . . . .
C22 C 0.63019(12) 0.3916(2) 0.20375(18) 0.0376(5) Uani 1 1 d . . . . .
H22 H 0.6494 0.3264 0.2444 0.045 Uiso 1 1 calc R U . . .
C23 C 0.55601(12) 0.4173(2) 0.19652(19) 0.0416(6) Uani 1 1 d . . . . .
C24 C 0.52723(12) 0.5162(2) 0.1412(2) 0.0459(6) Uani 1 1 d . . . . .
H24 H 0.4776 0.5324 0.1399 0.055 Uiso 1 1 calc R U . . .
C25 C 0.57161(12) 0.5921(2) 0.08737(19) 0.0423(6) Uani 1 1 d . . . . .
H25 H 0.5527 0.6596 0.0499 0.051 Uiso 1 1 calc R U . . .
C26 C 0.64440(11) 0.56414(19) 0.09111(17) 0.0340(5) Uani 1 1 d . . . . .
C27 C 0.78060(12) 0.3493(2) 0.07493(18) 0.0407(6) Uani 1 1 d . . . . .
H27 H 0.8286 0.3689 0.0514 0.049 Uiso 1 1 calc R U . . .
C28 C 0.79097(13) 0.2388(2) 0.14575(19) 0.0480(6) Uani 1 1 d . . . . .
H28A H 0.7444 0.2152 0.1700 0.058 Uiso 1 1 calc R U . . .
H28B H 0.8080 0.1739 0.1018 0.058 Uiso 1 1 calc R U . . .
C29 C 0.73272(14) 0.3262(2) -0.0263(2) 0.0455(6) Uani 1 1 d . . . . .
Cl1 Cl 0.49862(3) 0.31878(6) 0.25799(6) 0.0677(2) Uani 1 1 d . . . . .
N1 N 0.84307(9) 0.25804(17) 0.24228(15) 0.0424(5) Uani 1 1 d . . . . .
N2 N 0.86489(10) 0.52570(19) 0.40795(16) 0.0495(5) Uani 1 1 d . . . . .
N3 N 0.69918(9) 0.62489(16) 0.04043(15) 0.0378(5) Uani 1 1 d . . . . .
N4 N 0.69560(14) 0.3124(2) -0.1052(2) 0.0735(7) Uani 1 1 d . . . . .
O1 O 0.91174(10) 0.34442(17) 0.47013(15) 0.0644(5) Uani 1 1 d . . . . .
O2 O 0.79841(9) 0.66781(16) 0.30249(14) 0.0561(5) Uani 1 1 d . . . . .
O3 O 0.82267(9) 0.60571(15) 0.03384(14) 0.0543(5) 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 1.373(3) . ?
C1 C2 1.378(4) . ?
C1 H1 0.9300 . ?
C2 C3 1.363(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.371(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.369(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.377(3) . ?
C5 H5 0.9300 . ?
C6 N1 1.433(3) . ?
C7 O1 1.213(3) . ?
C7 N2 1.366(3) . ?
C7 C8 1.515(3) . ?
C8 N1 1.349(3) . ?
C8 C9 1.350(3) . ?
C9 C10 1.452(3) . ?
C9 C20 1.493(3) . ?
C10 O2 1.209(3) . ?
C10 N2 1.400(3) . ?
C11 N2 1.455(3) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 C13 1.373(4) . ?
C12 C17 1.380(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.365(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.364(5) . ?
C14 H14 0.9300 . ?
C15 C16 1.385(4) . ?
C15 H15 0.9300 . ?
C16 C17 1.378(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.504(3) . ?
C18 N3 1.455(3) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 O3 1.209(2) . ?
C19 N3 1.360(3) . ?
C19 C20 1.544(3) . ?
C20 C21 1.520(3) . ?
C20 C27 1.555(3) . ?
C21 C22 1.370(3) . ?
C21 C26 1.388(3) . ?
C22 C23 1.389(3) . ?
C22 H22 0.9300 . ?
C23 C24 1.371(3) . ?
C23 Cl1 1.741(2) . ?
C24 C25 1.384(3) . ?
C24 H24 0.9300 . ?
C25 C26 1.372(3) . ?
C25 H25 0.9300 . ?
C26 N3 1.405(3) . ?
C27 C29 1.462(3) . ?
C27 C28 1.504(3) . ?
C27 H27 0.9800 . ?
C28 N1 1.454(3) . ?
C28 H28A 0.9700 . ?
C28 H28B 0.9700 . ?
C29 N4 1.129(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 C1 C2 119.9(3) . . ?
C6 C1 H1 120.0 . . ?
C2 C1 H1 120.0 . . ?
C3 C2 C1 119.9(3) . . ?
C3 C2 H2 120.0 . . ?
C1 C2 H2 120.0 . . ?
C2 C3 C4 120.0(3) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C5 C4 C3 120.6(3) . . ?
C5 C4 H4 119.7 . . ?
C3 C4 H4 119.7 . . ?
C4 C5 C6 119.4(3) . . ?
C4 C5 H5 120.3 . . ?
C6 C5 H5 120.3 . . ?
C1 C6 C5 120.0(2) . . ?
C1 C6 N1 119.6(2) . . ?
C5 C6 N1 120.4(2) . . ?
O1 C7 N2 125.9(2) . . ?
O1 C7 C8 128.4(2) . . ?
N2 C7 C8 105.6(2) . . ?
N1 C8 C9 125.6(2) . . ?
N1 C8 C7 126.7(2) . . ?
C9 C8 C7 107.6(2) . . ?
C8 C9 C10 108.61(19) . . ?
C8 C9 C20 124.8(2) . . ?
C10 C9 C20 126.5(2) . . ?
O2 C10 N2 124.5(2) . . ?
O2 C10 C9 128.4(2) . . ?
N2 C10 C9 107.0(2) . . ?
N2 C11 H11A 109.5 . . ?
N2 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
N2 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C13 C12 C17 121.0(3) . . ?
C13 C12 H12 119.5 . . ?
C17 C12 H12 119.5 . . ?
C14 C13 C12 120.3(3) . . ?
C14 C13 H13 119.8 . . ?
C12 C13 H13 119.8 . . ?
C15 C14 C13 119.5(3) . . ?
C15 C14 H14 120.3 . . ?
C13 C14 H14 120.3 . . ?
C14 C15 C16 120.8(3) . . ?
C14 C15 H15 119.6 . . ?
C16 C15 H15 119.6 . . ?
C17 C16 C15 120.0(3) . . ?
C17 C16 H16 120.0 . . ?
C15 C16 H16 120.0 . . ?
C16 C17 C12 118.5(3) . . ?
C16 C17 C18 119.0(2) . . ?
C12 C17 C18 122.5(2) . . ?
N3 C18 C17 113.94(19) . . ?
N3 C18 H18A 108.8 . . ?
C17 C18 H18A 108.8 . . ?
N3 C18 H18B 108.8 . . ?
C17 C18 H18B 108.8 . . ?
H18A C18 H18B 107.7 . . ?
O3 C19 N3 126.1(2) . . ?
O3 C19 C20 125.4(2) . . ?
N3 C19 C20 108.46(18) . . ?
C9 C20 C21 115.08(17) . . ?
C9 C20 C19 112.99(17) . . ?
C21 C20 C19 101.50(16) . . ?
C9 C20 C27 104.82(17) . . ?
C21 C20 C27 114.35(17) . . ?
C19 C20 C27 108.16(17) . . ?
C22 C21 C26 120.05(19) . . ?
C22 C21 C20 131.17(19) . . ?
C26 C21 C20 108.78(18) . . ?
C21 C22 C23 117.9(2) . . ?
C21 C22 H22 121.1 . . ?
C23 C22 H22 121.1 . . ?
C24 C23 C22 121.8(2) . . ?
C24 C23 Cl1 119.75(17) . . ?
C22 C23 Cl1 118.44(18) . . ?
C23 C24 C25 120.4(2) . . ?
C23 C24 H24 119.8 . . ?
C25 C24 H24 119.8 . . ?
C26 C25 C24 117.7(2) . . ?
C26 C25 H25 121.2 . . ?
C24 C25 H25 121.2 . . ?
C25 C26 C21 122.1(2) . . ?
C25 C26 N3 128.0(2) . . ?
C21 C26 N3 109.90(17) . . ?
C29 C27 C28 111.55(19) . . ?
C29 C27 C20 111.63(18) . . ?
C28 C27 C20 114.00(19) . . ?
C29 C27 H27 106.4 . . ?
C28 C27 H27 106.4 . . ?
C20 C27 H27 106.4 . . ?
N1 C28 C27 112.03(19) . . ?
N1 C28 H28A 109.2 . . ?
C27 C28 H28A 109.2 . . ?
N1 C28 H28B 109.2 . . ?
C27 C28 H28B 109.2 . . ?
H28A C28 H28B 107.9 . . ?
N4 C29 C27 177.7(3) . . ?
C8 N1 C6 124.99(18) . . ?
C8 N1 C28 115.43(18) . . ?
C6 N1 C28 119.51(18) . . ?
C7 N2 C10 110.8(2) . . ?
C7 N2 C11 124.6(2) . . ?
C10 N2 C11 124.6(2) . . ?
C19 N3 C26 111.33(18) . . ?
C19 N3 C18 123.83(18) . . ?
C26 N3 C18 124.79(17) . . ?

_refine_diff_density_max         0.220
_refine_diff_density_min         -0.221
_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_5bb
_database_code_depnum_ccdc_archive 'CCDC 2189815'
loop_
_audit_author_name
_audit_author_address
'Chao-Guo Yan' 'Yangzhou University'
_audit_update_record             
;
2022-07-12 deposited with the CCDC.	2022-08-23 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         'C32 H26 N4 O5'
_chemical_formula_sum            'C32 H26 N4 O5'
_chemical_formula_weight         546.57

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                   9.0131(9)
_cell_length_b                   10.5429(11)
_cell_length_c                   14.4302(14)
_cell_angle_alpha                88.781(3)
_cell_angle_beta                 86.492(3)
_cell_angle_gamma                74.875(3)
_cell_volume                     1321.2(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5860
_cell_measurement_theta_min      2.34
_cell_measurement_theta_max      25.50

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.374
_exptl_crystal_F_000             572
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.095
_shelx_estimated_absorpt_T_min   0.974
_shelx_estimated_absorpt_T_max   0.981
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3662
_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            5066
_diffrn_reflns_av_unetI/netI     0.0931
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.345
_diffrn_reflns_theta_max         25.998
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             5066
_reflns_number_gt                3602
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 _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          
; 
 Refined as a 2-component twin. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0900P)²+1.6369P] 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         5066
_refine_ls_number_parameters     374
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1212
_refine_ls_R_factor_gt           0.0784
_refine_ls_wR_factor_ref         0.2125
_refine_ls_wR_factor_gt          0.1841
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_restrained_S_all      1.016
_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 0.5568(6) 0.5951(5) 0.1399(4) 0.0613(14) Uani 1 1 d . . . . .
H1 H 0.4796 0.6260 0.1859 0.074 Uiso 1 1 calc R U . . .
C2 C 0.6252(8) 0.6833(5) 0.0912(5) 0.0730(18) Uani 1 1 d . . . . .
H2 H 0.5937 0.7724 0.1050 0.088 Uiso 1 1 calc R U . . .
C3 C 0.7379(8) 0.6386(6) 0.0235(5) 0.0719(17) Uani 1 1 d . . . . .
H3 H 0.7831 0.6968 -0.0096 0.086 Uiso 1 1 calc R U . . .
C4 C 0.7832(7) 0.5083(6) 0.0052(4) 0.0699(17) Uani 1 1 d . . . . .
H4 H 0.8611 0.4774 -0.0404 0.084 Uiso 1 1 calc R U . . .
C5 C 0.7173(6) 0.4210(5) 0.0520(4) 0.0540(13) Uani 1 1 d . . . . .
H5 H 0.7505 0.3322 0.0374 0.065 Uiso 1 1 calc R U . . .
C6 C 0.6027(5) 0.4626(4) 0.1202(3) 0.0434(11) Uani 1 1 d . . . . .
C7 C 0.5240(5) 0.3683(5) 0.1693(4) 0.0502(12) Uani 1 1 d . . . . .
H7A H 0.4612 0.4124 0.2221 0.060 Uiso 1 1 calc R U . . .
H7B H 0.4558 0.3444 0.1273 0.060 Uiso 1 1 calc R U . . .
C8 C 0.6486(5) 0.1272(4) 0.1647(3) 0.0365(10) Uani 1 1 d . . . . .
C9 C 0.7726(4) 0.0290(4) 0.2184(3) 0.0296(9) Uani 1 1 d . . . . .
C10 C 0.8258(4) 0.1183(4) 0.2821(3) 0.0293(9) Uani 1 1 d . . . . .
C11 C 0.9349(5) 0.0921(4) 0.3472(3) 0.0331(9) Uani 1 1 d . . . . .
H11 H 0.9983 0.0076 0.3532 0.040 Uiso 1 1 calc R U . . .
C12 C 0.9505(6) 0.1923(4) 0.4043(3) 0.0406(10) Uani 1 1 d . . . . .
C13 C 1.0769(7) 0.1658(5) 0.4721(3) 0.0584(14) Uani 1 1 d . . . . .
H13A H 1.1708 0.1142 0.4424 0.088 Uiso 1 1 calc R U . . .
H13B H 1.0482 0.1189 0.5250 0.088 Uiso 1 1 calc R U . . .
H13C H 1.0919 0.2477 0.4919 0.088 Uiso 1 1 calc R U . . .
C14 C 0.8526(6) 0.3151(4) 0.3959(3) 0.0462(12) Uani 1 1 d . . . . .
H14 H 0.8610 0.3812 0.4353 0.055 Uiso 1 1 calc R U . . .
C15 C 0.7406(5) 0.3448(4) 0.3303(3) 0.0435(11) Uani 1 1 d . . . . .
H15 H 0.6754 0.4287 0.3252 0.052 Uiso 1 1 calc R U . . .
C16 C 0.7310(5) 0.2447(4) 0.2737(3) 0.0323(9) Uani 1 1 d . . . . .
C17 C 0.4450(6) -0.1816(6) 0.4440(4) 0.0590(14) Uani 1 1 d . . . . .
H17A H 0.4538 -0.2739 0.4510 0.089 Uiso 1 1 calc R U . . .
H17B H 0.3478 -0.1393 0.4192 0.089 Uiso 1 1 calc R U . . .
H17C H 0.4513 -0.1445 0.5033 0.089 Uiso 1 1 calc R U . . .
C18 C 0.5668(5) -0.0457(4) 0.3305(3) 0.0366(10) Uani 1 1 d . . . . .
C19 C 0.7119(5) -0.0695(4) 0.2743(3) 0.0318(9) Uani 1 1 d . . . . .
C20 C 0.7976(5) -0.1918(4) 0.2925(3) 0.0316(9) Uani 1 1 d . . . . .
C21 C 0.7058(5) -0.2559(4) 0.3617(3) 0.0345(9) Uani 1 1 d . . . . .
C22 C 1.1285(6) -0.4163(5) 0.3405(4) 0.0565(13) Uani 1 1 d . . . . .
H22 H 1.1461 -0.3518 0.3780 0.068 Uiso 1 1 calc R U . . .
C23 C 1.2085(7) -0.5466(6) 0.3516(5) 0.0708(18) Uani 1 1 d . . . . .
H23 H 1.2792 -0.5703 0.3973 0.085 Uiso 1 1 calc R U . . .
C24 C 1.1828(7) -0.6412(6) 0.2943(5) 0.073(2) Uani 1 1 d . . . . .
H24 H 1.2386 -0.7282 0.3005 0.088 Uiso 1 1 calc R U . . .
C25 C 1.0753(7) -0.6079(5) 0.2280(4) 0.0653(17) Uani 1 1 d . . . . .
H25 H 1.0576 -0.6721 0.1902 0.078 Uiso 1 1 calc R U . . .
C26 C 0.9943(6) -0.4785(4) 0.2186(3) 0.0486(12) Uani 1 1 d . . . . .
H26 H 0.9199 -0.4552 0.1750 0.058 Uiso 1 1 calc R U . . .
C27 C 1.0233(5) -0.3835(4) 0.2737(3) 0.0389(10) Uani 1 1 d . . . . .
C28 C 1.2783(5) 0.0275(5) 0.1308(4) 0.0535(13) Uani 1 1 d . . . . .
H28A H 1.2422 0.1206 0.1214 0.080 Uiso 1 1 calc R U . . .
H28B H 1.3406 -0.0116 0.0773 0.080 Uiso 1 1 calc R U . . .
H28C H 1.3384 0.0105 0.1846 0.080 Uiso 1 1 calc R U . . .
C29 C 1.1492(5) -0.1386(4) 0.1983(3) 0.0417(11) Uani 1 1 d . . . . .
C30 C 1.0026(5) -0.1787(4) 0.1815(3) 0.0350(9) Uani 1 1 d . . . . .
H30 H 1.0277 -0.2405 0.1296 0.042 Uiso 1 1 calc R U . . .
C31 C 0.8946(5) -0.0515(4) 0.1449(3) 0.0328(9) Uani 1 1 d . . . . .
H31 H 0.8417 -0.0724 0.0922 0.039 Uiso 1 1 calc R U . . .
C32 C 1.0049(5) 0.0278(4) 0.1109(3) 0.0346(10) Uani 1 1 d . . . . .
N1 N 0.6307(4) 0.2488(3) 0.2017(3) 0.0376(8) Uani 1 1 d . . . . .
N2 N 0.5699(4) -0.1616(3) 0.3805(3) 0.0419(9) Uani 1 1 d . . . . .
N3 N 0.9428(4) -0.2461(3) 0.2589(2) 0.0367(8) Uani 1 1 d . . . . .
N4 N 1.1476(4) -0.0285(3) 0.1448(3) 0.0382(8) Uani 1 1 d . . . . .
O1 O 0.5811(4) 0.0999(3) 0.1017(2) 0.0500(8) Uani 1 1 d . . . . .
O2 O 0.4612(4) 0.0532(3) 0.3358(3) 0.0533(9) Uani 1 1 d . . . . .
O3 O 0.7406(4) -0.3641(3) 0.3949(2) 0.0499(9) Uani 1 1 d . . . . .
O4 O 1.2519(4) -0.1922(3) 0.2463(3) 0.0611(10) Uani 1 1 d . . . . .
O5 O 0.9764(4) 0.1264(3) 0.0633(2) 0.0449(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 1.380(7) . ?
C1 C2 1.399(8) . ?
C1 H1 0.9300 . ?
C2 C3 1.362(9) . ?
C2 H2 0.9300 . ?
C3 C4 1.355(8) . ?
C3 H3 0.9300 . ?
C4 C5 1.366(8) . ?
C4 H4 0.9300 . ?
C5 C6 1.374(7) . ?
C5 H5 0.9300 . ?
C6 C7 1.506(7) . ?
C7 N1 1.459(5) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 O1 1.203(5) . ?
C8 N1 1.367(5) . ?
C8 C9 1.546(6) . ?
C9 C19 1.495(5) . ?
C9 C10 1.513(5) . ?
C9 C31 1.570(5) . ?
C10 C11 1.374(6) . ?
C10 C16 1.390(5) . ?
C11 C12 1.395(6) . ?
C11 H11 0.9300 . ?
C12 C14 1.371(6) . ?
C12 C13 1.514(7) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 C15 1.397(7) . ?
C14 H14 0.9300 . ?
C15 C16 1.372(6) . ?
C15 H15 0.9300 . ?
C16 N1 1.411(6) . ?
C17 N2 1.462(6) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 O2 1.214(5) . ?
C18 N2 1.401(5) . ?
C18 C19 1.463(6) . ?
C19 C20 1.349(6) . ?
C20 N3 1.349(5) . ?
C20 C21 1.517(6) . ?
C21 O3 1.199(5) . ?
C21 N2 1.377(5) . ?
C22 C27 1.368(7) . ?
C22 C23 1.386(8) . ?
C22 H22 0.9300 . ?
C23 C24 1.383(10) . ?
C23 H23 0.9300 . ?
C24 C25 1.377(10) . ?
C24 H24 0.9300 . ?
C25 C26 1.378(7) . ?
C25 H25 0.9300 . ?
C26 C27 1.379(7) . ?
C26 H26 0.9300 . ?
C27 N3 1.458(5) . ?
C28 N4 1.450(6) . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?
C29 O4 1.202(6) . ?
C29 N4 1.378(6) . ?
C29 C30 1.523(6) . ?
C30 N3 1.462(5) . ?
C30 C31 1.542(6) . ?
C30 H30 0.9800 . ?
C31 C32 1.510(6) . ?
C31 H31 0.9800 . ?
C32 O5 1.214(5) . ?
C32 N4 1.383(6) . ?

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 120.6(5) . . ?
C6 C1 H1 119.7 . . ?
C2 C1 H1 119.7 . . ?
C3 C2 C1 120.0(5) . . ?
C3 C2 H2 120.0 . . ?
C1 C2 H2 120.0 . . ?
C4 C3 C2 119.1(5) . . ?
C4 C3 H3 120.5 . . ?
C2 C3 H3 120.5 . . ?
C3 C4 C5 121.6(6) . . ?
C3 C4 H4 119.2 . . ?
C5 C4 H4 119.2 . . ?
C4 C5 C6 120.9(5) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 H5 119.5 . . ?
C5 C6 C1 117.8(5) . . ?
C5 C6 C7 121.4(4) . . ?
C1 C6 C7 120.7(5) . . ?
N1 C7 C6 113.5(4) . . ?
N1 C7 H7A 108.9 . . ?
C6 C7 H7A 108.9 . . ?
N1 C7 H7B 108.9 . . ?
C6 C7 H7B 108.9 . . ?
H7A C7 H7B 107.7 . . ?
O1 C8 N1 126.9(4) . . ?
O1 C8 C9 125.6(4) . . ?
N1 C8 C9 107.6(4) . . ?
C19 C9 C10 110.0(3) . . ?
C19 C9 C8 113.7(3) . . ?
C10 C9 C8 102.4(3) . . ?
C19 C9 C31 106.2(3) . . ?
C10 C9 C31 117.3(3) . . ?
C8 C9 C31 107.5(3) . . ?
C11 C10 C16 119.8(4) . . ?
C11 C10 C9 131.6(3) . . ?
C16 C10 C9 108.4(3) . . ?
C10 C11 C12 119.9(4) . . ?
C10 C11 H11 120.0 . . ?
C12 C11 H11 120.0 . . ?
C14 C12 C11 118.8(4) . . ?
C14 C12 C13 121.1(4) . . ?
C11 C12 C13 120.1(4) . . ?
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(4) . . ?
C12 C14 H14 118.7 . . ?
C15 C14 H14 118.7 . . ?
C16 C15 C14 117.1(4) . . ?
C16 C15 H15 121.5 . . ?
C14 C15 H15 121.5 . . ?
C15 C16 C10 121.8(4) . . ?
C15 C16 N1 128.4(4) . . ?
C10 C16 N1 109.8(3) . . ?
N2 C17 H17A 109.5 . . ?
N2 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
N2 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
O2 C18 N2 124.5(4) . . ?
O2 C18 C19 128.9(4) . . ?
N2 C18 C19 106.7(3) . . ?
C20 C19 C18 108.7(3) . . ?
C20 C19 C9 123.2(4) . . ?
C18 C19 C9 127.2(3) . . ?
C19 C20 N3 126.2(4) . . ?
C19 C20 C21 108.2(3) . . ?
N3 C20 C21 125.5(3) . . ?
O3 C21 N2 126.0(4) . . ?
O3 C21 C20 128.9(4) . . ?
N2 C21 C20 105.1(3) . . ?
C27 C22 C23 119.4(6) . . ?
C27 C22 H22 120.3 . . ?
C23 C22 H22 120.3 . . ?
C24 C23 C22 119.6(6) . . ?
C24 C23 H23 120.2 . . ?
C22 C23 H23 120.2 . . ?
C25 C24 C23 120.8(5) . . ?
C25 C24 H24 119.6 . . ?
C23 C24 H24 119.6 . . ?
C24 C25 C26 119.2(6) . . ?
C24 C25 H25 120.4 . . ?
C26 C25 H25 120.4 . . ?
C25 C26 C27 120.1(5) . . ?
C25 C26 H26 120.0 . . ?
C27 C26 H26 120.0 . . ?
C22 C27 C26 120.9(4) . . ?
C22 C27 N3 119.9(4) . . ?
C26 C27 N3 119.2(4) . . ?
N4 C28 H28A 109.5 . . ?
N4 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
N4 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
O4 C29 N4 124.5(4) . . ?
O4 C29 C30 128.3(4) . . ?
N4 C29 C30 107.2(4) . . ?
N3 C30 C29 115.5(4) . . ?
N3 C30 C31 117.4(3) . . ?
C29 C30 C31 103.5(3) . . ?
N3 C30 H30 106.6 . . ?
C29 C30 H30 106.6 . . ?
C31 C30 H30 106.6 . . ?
C32 C31 C30 102.9(3) . . ?
C32 C31 C9 110.1(3) . . ?
C30 C31 C9 115.5(3) . . ?
C32 C31 H31 109.3 . . ?
C30 C31 H31 109.3 . . ?
C9 C31 H31 109.3 . . ?
O5 C32 N4 123.9(4) . . ?
O5 C32 C31 127.2(4) . . ?
N4 C32 C31 108.9(3) . . ?
C8 N1 C16 111.4(3) . . ?
C8 N1 C7 124.2(4) . . ?
C16 N1 C7 124.3(4) . . ?
C21 N2 C18 111.3(3) . . ?
C21 N2 C17 123.9(4) . . ?
C18 N2 C17 124.8(4) . . ?
C20 N3 C27 123.3(3) . . ?
C20 N3 C30 117.2(3) . . ?
C27 N3 C30 116.5(3) . . ?
C29 N4 C32 112.6(3) . . ?
C29 N4 C28 123.7(4) . . ?
C32 N4 C28 123.6(4) . . ?

_refine_diff_density_max         0.258
_refine_diff_density_min         -0.304
_refine_diff_density_rms         0.069


####################################################################### 
# 
# 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_5e
_database_code_depnum_ccdc_archive 'CCDC 2189816'
loop_
_audit_author_name
_audit_author_address
'Chao-Guo Yan' 'Yangzhou University'
_audit_update_record             
;
2022-07-12 deposited with the CCDC.	2022-08-23 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 H28 N4 O5'
_chemical_formula_sum            'C29 H28 N4 O5'
_chemical_formula_weight         512.55

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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                   9.6086(10)
_cell_length_b                   29.328(3)
_cell_length_c                   9.6428(11)
_cell_angle_alpha                90
_cell_angle_beta                 101.287(3)
_cell_angle_gamma                90
_cell_volume                     2664.8(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    7942
_cell_measurement_theta_min      2.56
_cell_measurement_theta_max      25.05

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.278
_exptl_crystal_F_000             1080
_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    0.089
_shelx_estimated_absorpt_T_min   0.979
_shelx_estimated_absorpt_T_max   0.984
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6076
_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            26172
_diffrn_reflns_av_unetI/netI     0.0581
_diffrn_reflns_av_R_equivalents  0.0634
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -35
_diffrn_reflns_limit_k_max       36
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.563
_diffrn_reflns_theta_max         25.992
_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             5212
_reflns_number_gt                3336
_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)+(0.0622P)²+0.8835P] 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         5212
_refine_ls_number_parameters     347
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1006
_refine_ls_R_factor_gt           0.0551
_refine_ls_wR_factor_ref         0.1436
_refine_ls_wR_factor_gt          0.1232
_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 -0.1870(4) 0.29200(8) 0.3613(3) 0.0715(8) Uani 1 1 d . . . . .
H1 H -0.1085 0.2859 0.4321 0.086 Uiso 1 1 calc R U . . .
C2 C -0.2481(5) 0.33465(10) 0.3527(4) 0.0926(11) Uani 1 1 d . . . . .
H2 H -0.2112 0.3574 0.4165 0.111 Uiso 1 1 calc R U . . .
C3 C -0.3637(4) 0.34293(11) 0.2490(4) 0.0854(11) Uani 1 1 d . . . . .
H3 H -0.4057 0.3716 0.2427 0.102 Uiso 1 1 calc R U . . .
C4 C -0.4192(3) 0.30992(11) 0.1540(4) 0.0744(9) Uani 1 1 d . . . . .
H4 H -0.4985 0.3161 0.0844 0.089 Uiso 1 1 calc R U . . .
C5 C -0.3558(2) 0.26643(8) 0.1620(3) 0.0562(7) Uani 1 1 d . . . . .
H5 H -0.3917 0.2438 0.0974 0.067 Uiso 1 1 calc R U . . .
C6 C -0.2407(2) 0.25829(7) 0.2665(2) 0.0441(6) Uani 1 1 d . . . . .
C7 C 0.0532(2) 0.23741(8) 0.2191(2) 0.0471(6) Uani 1 1 d . . . . .
C8 C -0.0375(2) 0.20678(7) 0.2889(2) 0.0350(5) Uani 1 1 d . . . . .
C9 C 0.0415(2) 0.17159(7) 0.3487(2) 0.0367(5) Uani 1 1 d . . . . .
C10 C 0.1865(3) 0.17833(9) 0.3276(3) 0.0551(6) Uani 1 1 d . . . . .
C11 C 0.3081(3) 0.23762(12) 0.2021(5) 0.1089(14) Uani 1 1 d . . . . .
H11A H 0.3677 0.2130 0.1836 0.163 Uiso 1 1 calc R U . . .
H11B H 0.3608 0.2572 0.2733 0.163 Uiso 1 1 calc R U . . .
H11C H 0.2766 0.2547 0.1169 0.163 Uiso 1 1 calc R U . . .
C12 C -0.3581(2) 0.14946(7) 0.2611(2) 0.0437(6) Uani 1 1 d . . . . .
C13 C -0.2502(2) 0.17967(7) 0.3542(2) 0.0351(5) Uani 1 1 d . . . . .
H13 H -0.3034 0.1972 0.4130 0.042 Uiso 1 1 calc R U . . .
C14 C -0.1580(2) 0.14585(6) 0.4548(2) 0.0338(5) Uani 1 1 d . . . . .
H14 H -0.1376 0.1588 0.5503 0.041 Uiso 1 1 calc R U . . .
C15 C -0.2570(2) 0.10560(7) 0.4522(2) 0.0394(5) Uani 1 1 d . . . . .
C16 C -0.4753(3) 0.07550(9) 0.2961(3) 0.0679(8) Uani 1 1 d . . . . .
H16A H -0.4443 0.0545 0.2321 0.102 Uiso 1 1 calc R U . . .
H16B H -0.5621 0.0897 0.2502 0.102 Uiso 1 1 calc R U . . .
H16C H -0.4909 0.0594 0.3784 0.102 Uiso 1 1 calc R U . . .
C17 C 0.3272(3) -0.03386(11) 0.0677(3) 0.0817(9) Uani 1 1 d . . . . .
H17A H 0.3317 -0.0083 0.0065 0.123 Uiso 1 1 calc R U . . .
H17B H 0.3259 -0.0616 0.0148 0.123 Uiso 1 1 calc R U . . .
H17C H 0.4088 -0.0336 0.1433 0.123 Uiso 1 1 calc R U . . .
C18 C 0.1948(3) -0.03070(8) 0.1280(2) 0.0532(6) Uani 1 1 d . . . . .
H18A H 0.1925 -0.0562 0.1916 0.064 Uiso 1 1 calc R U . . .
H18B H 0.1130 -0.0333 0.0515 0.064 Uiso 1 1 calc R U . . .
C19 C 0.1834(3) 0.01318(8) 0.2073(3) 0.0527(6) Uani 1 1 d . . . . .
H19A H 0.2673 0.0166 0.2809 0.063 Uiso 1 1 calc R U . . .
H19B H 0.1804 0.0387 0.1426 0.063 Uiso 1 1 calc R U . . .
C20 C 0.0539(2) 0.01466(7) 0.2731(2) 0.0423(5) Uani 1 1 d . . . . .
H20A H -0.0302 0.0117 0.1994 0.051 Uiso 1 1 calc R U . . .
H20B H 0.0561 -0.0111 0.3367 0.051 Uiso 1 1 calc R U . . .
C21 C -0.0388(2) 0.09262(7) 0.3000(2) 0.0373(5) Uani 1 1 d . . . . .
C22 C -0.0164(2) 0.13110(7) 0.4131(2) 0.0342(5) Uani 1 1 d . . . . .
C23 C 0.0854(2) 0.10872(7) 0.5327(2) 0.0365(5) Uani 1 1 d . . . . .
C24 C 0.1426(2) 0.12388(8) 0.6662(2) 0.0476(6) Uani 1 1 d . . . . .
H24 H 0.1187 0.1525 0.6957 0.057 Uiso 1 1 calc R U . . .
C25 C 0.2371(3) 0.09598(9) 0.7579(2) 0.0564(7) Uani 1 1 d . . . . .
C26 C 0.2992(4) 0.11234(12) 0.9053(3) 0.0921(11) Uani 1 1 d . . . . .
H26A H 0.3549 0.0884 0.9569 0.138 Uiso 1 1 calc R U . . .
H26B H 0.2239 0.1206 0.9528 0.138 Uiso 1 1 calc R U . . .
H26C H 0.3584 0.1384 0.9001 0.138 Uiso 1 1 calc R U . . .
C27 C 0.2702(3) 0.05376(9) 0.7104(3) 0.0583(7) Uani 1 1 d . . . . .
H27 H 0.3338 0.0354 0.7708 0.070 Uiso 1 1 calc R U . . .
C28 C 0.2130(2) 0.03765(8) 0.5767(3) 0.0501(6) Uani 1 1 d . . . . .
H28 H 0.2367 0.0091 0.5467 0.060 Uiso 1 1 calc R U . . .
C29 C 0.1196(2) 0.06561(7) 0.4901(2) 0.0374(5) Uani 1 1 d . . . . .
N1 N -0.17854(18) 0.21317(5) 0.28137(18) 0.0385(4) Uani 1 1 d . . . . .
N2 N 0.1862(2) 0.21942(7) 0.2512(3) 0.0660(6) Uani 1 1 d . . . . .
N3 N -0.36713(19) 0.11023(6) 0.33816(19) 0.0444(5) Uani 1 1 d . . . . .
N4 N 0.04416(18) 0.05679(5) 0.35146(17) 0.0384(4) Uani 1 1 d . . . . .
O1 O 0.01780(18) 0.27027(6) 0.14488(19) 0.0641(5) Uani 1 1 d . . . . .
O2 O 0.29174(19) 0.15538(7) 0.3648(2) 0.0821(6) Uani 1 1 d . . . . .
O3 O -0.42948(18) 0.15787(6) 0.14685(18) 0.0635(5) Uani 1 1 d . . . . .
O4 O -0.24104(18) 0.07335(5) 0.53134(17) 0.0543(4) Uani 1 1 d . . . . .
O5 O -0.11674(18) 0.09530(5) 0.18461(16) 0.0554(5) 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 1.377(3) . ?
C1 C2 1.377(4) . ?
C1 H1 0.9300 . ?
C2 C3 1.363(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.367(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.409(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.364(3) . ?
C5 H5 0.9300 . ?
C6 N1 1.447(3) . ?
C7 O1 1.209(3) . ?
C7 N2 1.361(3) . ?
C7 C8 1.499(3) . ?
C8 C9 1.343(3) . ?
C8 N1 1.356(3) . ?
C9 C10 1.460(3) . ?
C9 C22 1.497(3) . ?
C10 O2 1.209(3) . ?
C10 N2 1.412(3) . ?
C11 N2 1.448(3) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 O3 1.204(3) . ?
C12 N3 1.382(3) . ?
C12 C13 1.517(3) . ?
C13 N1 1.457(3) . ?
C13 C14 1.540(3) . ?
C13 H13 0.9800 . ?
C14 C15 1.513(3) . ?
C14 C22 1.554(3) . ?
C14 H14 0.9800 . ?
C15 O4 1.206(2) . ?
C15 N3 1.376(3) . ?
C16 N3 1.455(3) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 C18 1.502(4) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 C19 1.512(3) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 C20 1.504(3) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 N4 1.461(3) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C21 O5 1.216(2) . ?
C21 N4 1.353(3) . ?
C21 C22 1.555(3) . ?
C22 C23 1.509(3) . ?
C23 C24 1.371(3) . ?
C23 C29 1.389(3) . ?
C24 C25 1.401(3) . ?
C24 H24 0.9300 . ?
C25 C27 1.379(4) . ?
C25 C26 1.509(4) . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
C27 C28 1.382(3) . ?
C27 H27 0.9300 . ?
C28 C29 1.371(3) . ?
C28 H28 0.9300 . ?
C29 N4 1.414(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 C1 C2 120.8(3) . . ?
C6 C1 H1 119.6 . . ?
C2 C1 H1 119.6 . . ?
C3 C2 C1 118.9(3) . . ?
C3 C2 H2 120.6 . . ?
C1 C2 H2 120.6 . . ?
C2 C3 C4 121.3(3) . . ?
C2 C3 H3 119.3 . . ?
C4 C3 H3 119.3 . . ?
C3 C4 C5 119.8(3) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 H4 120.1 . . ?
C6 C5 C4 118.6(3) . . ?
C6 C5 H5 120.7 . . ?
C4 C5 H5 120.7 . . ?
C5 C6 C1 120.6(2) . . ?
C5 C6 N1 119.5(2) . . ?
C1 C6 N1 119.8(2) . . ?
O1 C7 N2 125.9(2) . . ?
O1 C7 C8 128.5(2) . . ?
N2 C7 C8 105.56(19) . . ?
C9 C8 N1 127.16(19) . . ?
C9 C8 C7 108.91(19) . . ?
N1 C8 C7 123.78(18) . . ?
C8 C9 C10 108.09(19) . . ?
C8 C9 C22 124.30(19) . . ?
C10 C9 C22 127.39(19) . . ?
O2 C10 N2 123.1(2) . . ?
O2 C10 C9 130.4(2) . . ?
N2 C10 C9 106.50(19) . . ?
N2 C11 H11A 109.5 . . ?
N2 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
N2 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O3 C12 N3 125.3(2) . . ?
O3 C12 C13 128.5(2) . . ?
N3 C12 C13 106.01(17) . . ?
N1 C13 C12 116.18(17) . . ?
N1 C13 C14 118.03(16) . . ?
C12 C13 C14 103.83(16) . . ?
N1 C13 H13 105.9 . . ?
C12 C13 H13 105.9 . . ?
C14 C13 H13 105.9 . . ?
C15 C14 C13 102.09(16) . . ?
C15 C14 C22 110.98(16) . . ?
C13 C14 C22 116.18(16) . . ?
C15 C14 H14 109.1 . . ?
C13 C14 H14 109.1 . . ?
C22 C14 H14 109.1 . . ?
O4 C15 N3 124.5(2) . . ?
O4 C15 C14 126.9(2) . . ?
N3 C15 C14 108.60(17) . . ?
N3 C16 H16A 109.5 . . ?
N3 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
N3 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C18 C17 H17A 109.5 . . ?
C18 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C18 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C17 C18 C19 113.5(2) . . ?
C17 C18 H18A 108.9 . . ?
C19 C18 H18A 108.9 . . ?
C17 C18 H18B 108.9 . . ?
C19 C18 H18B 108.9 . . ?
H18A C18 H18B 107.7 . . ?
C20 C19 C18 112.71(19) . . ?
C20 C19 H19A 109.1 . . ?
C18 C19 H19A 109.1 . . ?
C20 C19 H19B 109.1 . . ?
C18 C19 H19B 109.1 . . ?
H19A C19 H19B 107.8 . . ?
N4 C20 C19 112.62(18) . . ?
N4 C20 H20A 109.1 . . ?
C19 C20 H20A 109.1 . . ?
N4 C20 H20B 109.1 . . ?
C19 C20 H20B 109.1 . . ?
H20A C20 H20B 107.8 . . ?
O5 C21 N4 126.76(19) . . ?
O5 C21 C22 124.83(18) . . ?
N4 C21 C22 108.41(16) . . ?
C9 C22 C23 115.12(17) . . ?
C9 C22 C14 107.56(16) . . ?
C23 C22 C14 113.12(16) . . ?
C9 C22 C21 107.27(16) . . ?
C23 C22 C21 101.58(16) . . ?
C14 C22 C21 112.05(16) . . ?
C24 C23 C29 119.91(19) . . ?
C24 C23 C22 131.11(19) . . ?
C29 C23 C22 108.98(16) . . ?
C23 C24 C25 119.6(2) . . ?
C23 C24 H24 120.2 . . ?
C25 C24 H24 120.2 . . ?
C27 C25 C24 118.6(2) . . ?
C27 C25 C26 121.6(2) . . ?
C24 C25 C26 119.8(2) . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C25 C27 C28 122.8(2) . . ?
C25 C27 H27 118.6 . . ?
C28 C27 H27 118.6 . . ?
C29 C28 C27 117.2(2) . . ?
C29 C28 H28 121.4 . . ?
C27 C28 H28 121.4 . . ?
C28 C29 C23 121.90(19) . . ?
C28 C29 N4 128.3(2) . . ?
C23 C29 N4 109.82(17) . . ?
C8 N1 C6 121.34(17) . . ?
C8 N1 C13 116.28(16) . . ?
C6 N1 C13 116.10(17) . . ?
C7 N2 C10 110.79(19) . . ?
C7 N2 C11 124.5(2) . . ?
C10 N2 C11 124.5(2) . . ?
C15 N3 C12 113.11(18) . . ?
C15 N3 C16 123.33(19) . . ?
C12 N3 C16 123.37(19) . . ?
C21 N4 C29 111.14(16) . . ?
C21 N4 C20 124.06(17) . . ?
C29 N4 C20 124.79(17) . . ?

_refine_diff_density_max         0.205
_refine_diff_density_min         -0.203
_refine_diff_density_rms         0.043


####################################################################### 
# 
# 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_5ee
_database_code_depnum_ccdc_archive 'CCDC 2189817'
loop_
_audit_author_name
_audit_author_address
'Chao-Guo Yan' 'Yangzhou University'
_audit_update_record             
;
2022-07-12 deposited with the CCDC.	2022-08-23 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 H28 N4 O5'
_chemical_formula_sum            'C29 H28 N4 O5'
_chemical_formula_weight         512.55

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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                   11.1314(6)
_cell_length_b                   9.2504(5)
_cell_length_c                   25.5543(16)
_cell_angle_alpha                90
_cell_angle_beta                 100.241(2)
_cell_angle_gamma                90
_cell_volume                     2589.4(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    7008
_cell_measurement_theta_min      2.43
_cell_measurement_theta_max      22.71

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.315
_exptl_crystal_F_000             1080
_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    0.091
_shelx_estimated_absorpt_T_min   0.978
_shelx_estimated_absorpt_T_max   0.984
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6599
_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            24790
_diffrn_reflns_av_unetI/netI     0.0415
_diffrn_reflns_av_R_equivalents  0.0488
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         2.238
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_full        25.000
_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             4546
_reflns_number_gt                2791
_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)+(0.1521P)²+0.0865P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.011(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4546
_refine_ls_number_parameters     386
_refine_ls_number_restraints     171
_refine_ls_R_factor_all          0.1178
_refine_ls_R_factor_gt           0.0704
_refine_ls_wR_factor_ref         0.2351
_refine_ls_wR_factor_gt          0.2111
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_restrained_S_all      1.140
_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 0.9025(3) 0.2441(5) 0.23323(16) 0.0934(13) Uani 1 1 d . . . . .
H1 H 0.8506 0.1879 0.2496 0.112 Uiso 1 1 calc R U . . .
C2 C 1.0259(4) 0.2502(6) 0.25421(18) 0.1146(16) Uani 1 1 d . . . . .
H2 H 1.0574 0.1958 0.2841 0.138 Uiso 1 1 calc R U . . .
C3 C 1.1012(3) 0.3354(6) 0.23115(18) 0.0998(13) Uani 1 1 d . . . . .
H3 H 1.1838 0.3413 0.2458 0.120 Uiso 1 1 calc R U . . .
C4 C 1.0556(3) 0.4119(4) 0.18669(17) 0.0887(12) Uani 1 1 d . . . . .
H4 H 1.1080 0.4686 0.1707 0.106 Uiso 1 1 calc R U . . .
C5 C 0.9321(3) 0.4073(4) 0.16458(14) 0.0723(9) Uani 1 1 d . . . . .
H5 H 0.9011 0.4611 0.1345 0.087 Uiso 1 1 calc R U . . .
C6 C 0.8574(2) 0.3211(3) 0.18852(12) 0.0594(8) Uani 1 1 d . . . . .
C7 C 0.7442(3) 0.1012(3) 0.10670(12) 0.0615(7) Uani 1 1 d . U . . .
C8 C 0.6753(2) 0.2076(3) 0.13652(11) 0.0518(7) Uani 1 1 d . U . . .
C9 C 0.5557(2) 0.1748(3) 0.12476(10) 0.0490(7) Uani 1 1 d . U . . .
C10 C 0.5417(3) 0.0502(3) 0.08968(11) 0.0565(7) Uani 1 1 d . U . . .
C11 C 0.6823(3) -0.1124(4) 0.04858(14) 0.0799(10) Uani 1 1 d . U . . .
H11A H 0.7232 -0.0785 0.0209 0.120 Uiso 1 1 calc R U . . .
H11B H 0.6070 -0.1583 0.0331 0.120 Uiso 1 1 calc R U . . .
H11C H 0.7334 -0.1807 0.0704 0.120 Uiso 1 1 calc R U . . .
C12 C 0.0283(13) -0.2652(11) 0.0701(5) 0.145(3) Uani 0.473(5) 1 d D U P A 1
H12A H -0.0432 -0.2337 0.0461 0.218 Uiso 0.473(5) 1 calc R U P A 1
H12B H 0.0172 -0.3631 0.0807 0.218 Uiso 0.473(5) 1 calc R U P A 1
H12C H 0.0979 -0.2600 0.0528 0.218 Uiso 0.473(5) 1 calc R U P A 1
C13 C 0.0491(9) -0.1675(9) 0.1194(4) 0.116(2) Uani 0.473(5) 1 d D U P A 1
H13A H -0.0271 -0.1208 0.1228 0.139 Uiso 0.473(5) 1 calc R U P A 1
H13B H 0.0750 -0.2260 0.1508 0.139 Uiso 0.473(5) 1 calc R U P A 1
C14 C 0.1440(8) -0.0542(8) 0.1158(4) 0.0991(16) Uani 0.473(5) 1 d D U P A 1
H14A H 0.1333 -0.0233 0.0790 0.119 Uiso 0.473(5) 1 calc R U P A 1
H14B H 0.2232 -0.1009 0.1240 0.119 Uiso 0.473(5) 1 calc R U P A 1
C15 C 0.1498(9) 0.0815(8) 0.1500(4) 0.0753(19) Uani 0.473(5) 1 d D U P A 1
H15A H 0.1659 0.0574 0.1875 0.090 Uiso 0.473(5) 1 calc R U P A 1
H15B H 0.0742 0.1358 0.1421 0.090 Uiso 0.473(5) 1 calc R U P A 1
C12' C 0.0579(11) -0.2657(10) 0.1076(4) 0.145(3) Uani 0.527(5) 1 d D U P A 2
H12D H 0.0911 -0.3522 0.0950 0.217 Uiso 0.527(5) 1 calc R U P A 2
H12E H -0.0223 -0.2853 0.1148 0.217 Uiso 0.527(5) 1 calc R U P A 2
H12F H 0.1097 -0.2337 0.1396 0.217 Uiso 0.527(5) 1 calc R U P A 2
C13' C 0.0503(7) -0.1483(8) 0.0653(3) 0.1125(17) Uani 0.527(5) 1 d D U P A 2
H13C H 0.0518 -0.1930 0.0311 0.135 Uiso 0.527(5) 1 calc R U P A 2
H13D H -0.0267 -0.0975 0.0630 0.135 Uiso 0.527(5) 1 calc R U P A 2
C14' C 0.1522(7) -0.0425(7) 0.0771(3) 0.0933(17) Uani 0.527(5) 1 d D U P A 2
H14C H 0.1515 0.0159 0.0455 0.112 Uiso 0.527(5) 1 calc R U P A 2
H14D H 0.2281 -0.0964 0.0830 0.112 Uiso 0.527(5) 1 calc R U P A 2
C15' C 0.1544(9) 0.0609(9) 0.1244(3) 0.0840(18) Uani 0.527(5) 1 d D U P A 2
H15C H 0.0781 0.1141 0.1189 0.101 Uiso 0.527(5) 1 calc R U P A 2
H15D H 0.1571 0.0030 0.1563 0.101 Uiso 0.527(5) 1 calc R U P A 2
C16 C 0.3675(3) 0.1490(3) 0.16403(12) 0.0535(7) Uani 1 1 d . . . . .
C17 C 0.4570(2) 0.2560(3) 0.14433(10) 0.0476(7) Uani 1 1 d . . . . .
C18 C 0.3724(2) 0.3344(3) 0.10020(11) 0.0505(7) Uani 1 1 d . . . . .
C19 C 0.3932(3) 0.4445(3) 0.06655(11) 0.0622(8) Uani 1 1 d . . . . .
H19 H 0.4712 0.4834 0.0694 0.075 Uiso 1 1 calc R U . . .
C20 C 0.2995(4) 0.4979(4) 0.02859(13) 0.0745(10) Uani 1 1 d . . . . .
C21 C 0.3196(4) 0.6203(5) -0.00743(16) 0.1143(16) Uani 1 1 d . . . . .
H21A H 0.3963 0.6660 0.0060 0.171 Uiso 1 1 calc R U . . .
H21B H 0.2549 0.6895 -0.0088 0.171 Uiso 1 1 calc R U . . .
H21C H 0.3205 0.5836 -0.0425 0.171 Uiso 1 1 calc R U . . .
C22 C 0.1860(4) 0.4335(4) 0.02546(15) 0.0878(12) Uani 1 1 d . . . . .
H22 H 0.1227 0.4656 -0.0007 0.105 Uiso 1 1 calc R U . . .
C23 C 0.1617(3) 0.3248(4) 0.05876(16) 0.0813(11) Uani 1 1 d . . . . .
H23 H 0.0837 0.2863 0.0562 0.098 Uiso 1 1 calc R U . . .
C24 C 0.2569(3) 0.2757(3) 0.09584(12) 0.0602(8) Uani 1 1 d . . . . .
C25 C 0.4468(3) 0.4882(3) 0.19494(11) 0.0560(8) Uani 1 1 d . . . . .
C26 C 0.5178(2) 0.3497(3) 0.19332(11) 0.0497(7) Uani 1 1 d . . . . .
H26 H 0.5182 0.2953 0.2262 0.060 Uiso 1 1 calc R U . . .
C27 C 0.6471(2) 0.4054(3) 0.19162(11) 0.0514(7) Uani 1 1 d . . . . .
H27 H 0.6870 0.4201 0.2286 0.062 Uiso 1 1 calc R U . . .
C28 C 0.6238(3) 0.5550(3) 0.16723(12) 0.0620(8) Uani 1 1 d . . . . .
C29 C 0.4613(4) 0.7419(3) 0.16192(16) 0.0903(12) Uani 1 1 d . . . . .
H29A H 0.4464 0.7535 0.1240 0.135 Uiso 1 1 calc R U . . .
H29B H 0.5187 0.8137 0.1779 0.135 Uiso 1 1 calc R U . . .
H29C H 0.3861 0.7533 0.1749 0.135 Uiso 1 1 calc R U . . .
N1 N 0.7276(2) 0.3160(3) 0.16740(9) 0.0573(7) Uani 1 1 d . . . . .
N2 N 0.6569(2) 0.0092(3) 0.08096(10) 0.0635(7) Uani 1 1 d . U . . .
N3 N 0.2557(2) 0.1666(3) 0.13448(11) 0.0658(7) Uani 1 1 d . . . . .
N4 N 0.5110(2) 0.5980(2) 0.17561(10) 0.0595(7) Uani 1 1 d . . . . .
O1 O 0.8512(2) 0.1010(3) 0.10465(10) 0.0882(8) Uani 1 1 d . U . . .
O2 O 0.4476(2) -0.0130(2) 0.07044(9) 0.0732(7) Uani 1 1 d . U . . .
O3 O 0.39385(19) 0.0642(2) 0.20084(9) 0.0676(6) Uani 1 1 d . . . . .
O4 O 0.3483(2) 0.5030(2) 0.20775(9) 0.0776(7) Uani 1 1 d . . . . .
O5 O 0.6921(2) 0.6256(3) 0.14583(11) 0.0930(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 1.364(5) . ?
C1 C2 1.384(5) . ?
C1 H1 0.9300 . ?
C2 C3 1.359(6) . ?
C2 H2 0.9300 . ?
C3 C4 1.358(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.391(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.372(4) . ?
C5 H5 0.9300 . ?
C6 N1 1.451(4) . ?
C7 O1 1.202(3) . ?
C7 N2 1.369(4) . ?
C7 C8 1.531(4) . ?
C8 N1 1.343(4) . ?
C8 C9 1.346(4) . ?
C9 C10 1.452(4) . ?
C9 C17 1.490(4) . ?
C10 O2 1.223(3) . ?
C10 N2 1.392(4) . ?
C11 N2 1.453(4) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 C13 1.533(5) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 C14 1.502(5) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C15 1.524(5) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 N3 1.527(9) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C12' C13' 1.523(5) . ?
C12' H12D 0.9600 . ?
C12' H12E 0.9600 . ?
C12' H12F 0.9600 . ?
C13' C14' 1.488(5) . ?
C13' H13C 0.9700 . ?
C13' H13D 0.9700 . ?
C14' C15' 1.539(5) . ?
C14' H14C 0.9700 . ?
C14' H14D 0.9700 . ?
C15' N3 1.480(9) . ?
C15' H15C 0.9700 . ?
C15' H15D 0.9700 . ?
C16 O3 1.220(3) . ?
C16 N3 1.346(4) . ?
C16 C17 1.550(4) . ?
C17 C18 1.518(4) . ?
C17 C26 1.573(4) . ?
C18 C19 1.379(4) . ?
C18 C24 1.382(4) . ?
C19 C20 1.383(5) . ?
C19 H19 0.9300 . ?
C20 C22 1.387(5) . ?
C20 C21 1.501(5) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 C23 1.375(5) . ?
C22 H22 0.9300 . ?
C23 C24 1.368(4) . ?
C23 H23 0.9300 . ?
C24 N3 1.414(4) . ?
C25 O4 1.207(3) . ?
C25 N4 1.382(4) . ?
C25 C26 1.510(4) . ?
C26 C27 1.537(4) . ?
C26 H26 0.9800 . ?
C27 N1 1.438(3) . ?
C27 C28 1.521(4) . ?
C27 H27 0.9800 . ?
C28 O5 1.205(4) . ?
C28 N4 1.370(4) . ?
C29 N4 1.461(4) . ?
C29 H29A 0.9600 . ?
C29 H29B 0.9600 . ?
C29 H29C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 C1 C2 119.7(3) . . ?
C6 C1 H1 120.1 . . ?
C2 C1 H1 120.1 . . ?
C3 C2 C1 120.1(4) . . ?
C3 C2 H2 119.9 . . ?
C1 C2 H2 119.9 . . ?
C4 C3 C2 119.8(3) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
C3 C4 C5 121.3(3) . . ?
C3 C4 H4 119.4 . . ?
C5 C4 H4 119.4 . . ?
C6 C5 C4 118.1(3) . . ?
C6 C5 H5 121.0 . . ?
C4 C5 H5 121.0 . . ?
C1 C6 C5 121.0(3) . . ?
C1 C6 N1 119.3(3) . . ?
C5 C6 N1 119.7(3) . . ?
O1 C7 N2 127.1(3) . . ?
O1 C7 C8 127.6(3) . . ?
N2 C7 C8 105.3(2) . . ?
N1 C8 C9 127.4(2) . . ?
N1 C8 C7 124.7(2) . . ?
C9 C8 C7 107.9(3) . . ?
C8 C9 C10 108.1(2) . . ?
C8 C9 C17 124.8(2) . . ?
C10 C9 C17 127.1(2) . . ?
O2 C10 N2 123.5(3) . . ?
O2 C10 C9 128.2(3) . . ?
N2 C10 C9 108.3(3) . . ?
N2 C11 H11A 109.5 . . ?
N2 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
N2 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C13 C12 H12A 109.5 . . ?
C13 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C13 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C14 C13 C12 111.5(6) . . ?
C14 C13 H13A 109.3 . . ?
C12 C13 H13A 109.3 . . ?
C14 C13 H13B 109.3 . . ?
C12 C13 H13B 109.3 . . ?
H13A C13 H13B 108.0 . . ?
C13 C14 C15 119.9(6) . . ?
C13 C14 H14A 107.4 . . ?
C15 C14 H14A 107.4 . . ?
C13 C14 H14B 107.4 . . ?
C15 C14 H14B 107.4 . . ?
H14A C14 H14B 106.9 . . ?
C14 C15 N3 103.4(5) . . ?
C14 C15 H15A 111.1 . . ?
N3 C15 H15A 111.1 . . ?
C14 C15 H15B 111.1 . . ?
N3 C15 H15B 111.1 . . ?
H15A C15 H15B 109.0 . . ?
C13' C12' H12D 109.5 . . ?
C13' C12' H12E 109.5 . . ?
H12D C12' H12E 109.5 . . ?
C13' C12' H12F 109.5 . . ?
H12D C12' H12F 109.5 . . ?
H12E C12' H12F 109.5 . . ?
C14' C13' C12' 112.4(6) . . ?
C14' C13' H13C 109.1 . . ?
C12' C13' H13C 109.1 . . ?
C14' C13' H13D 109.1 . . ?
C12' C13' H13D 109.1 . . ?
H13C C13' H13D 107.9 . . ?
C13' C14' C15' 118.2(6) . . ?
C13' C14' H14C 107.8 . . ?
C15' C14' H14C 107.8 . . ?
C13' C14' H14D 107.8 . . ?
C15' C14' H14D 107.8 . . ?
H14C C14' H14D 107.1 . . ?
N3 C15' C14' 116.9(6) . . ?
N3 C15' H15C 108.1 . . ?
C14' C15' H15C 108.1 . . ?
N3 C15' H15D 108.1 . . ?
C14' C15' H15D 108.1 . . ?
H15C C15' H15D 107.3 . . ?
O3 C16 N3 125.6(3) . . ?
O3 C16 C17 125.5(3) . . ?
N3 C16 C17 108.9(3) . . ?
C9 C17 C18 112.8(2) . . ?
C9 C17 C16 110.0(2) . . ?
C18 C17 C16 101.3(2) . . ?
C9 C17 C26 107.8(2) . . ?
C18 C17 C26 116.7(2) . . ?
C16 C17 C26 107.7(2) . . ?
C19 C18 C24 119.8(3) . . ?
C19 C18 C17 131.7(3) . . ?
C24 C18 C17 108.5(2) . . ?
C18 C19 C20 120.8(3) . . ?
C18 C19 H19 119.6 . . ?
C20 C19 H19 119.6 . . ?
C19 C20 C22 116.9(3) . . ?
C19 C20 C21 121.6(4) . . ?
C22 C20 C21 121.5(4) . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C23 C22 C20 123.8(3) . . ?
C23 C22 H22 118.1 . . ?
C20 C22 H22 118.1 . . ?
C24 C23 C22 117.2(3) . . ?
C24 C23 H23 121.4 . . ?
C22 C23 H23 121.4 . . ?
C23 C24 C18 121.4(3) . . ?
C23 C24 N3 128.2(3) . . ?
C18 C24 N3 110.4(2) . . ?
O4 C25 N4 124.5(3) . . ?
O4 C25 C26 127.5(3) . . ?
N4 C25 C26 107.9(2) . . ?
C25 C26 C27 102.3(2) . . ?
C25 C26 C17 109.7(2) . . ?
C27 C26 C17 115.8(2) . . ?
C25 C26 H26 109.6 . . ?
C27 C26 H26 109.6 . . ?
C17 C26 H26 109.6 . . ?
N1 C27 C28 114.9(2) . . ?
N1 C27 C26 118.5(2) . . ?
C28 C27 C26 103.0(2) . . ?
N1 C27 H27 106.5 . . ?
C28 C27 H27 106.5 . . ?
C26 C27 H27 106.5 . . ?
O5 C28 N4 125.7(3) . . ?
O5 C28 C27 127.2(3) . . ?
N4 C28 C27 107.1(3) . . ?
N4 C29 H29A 109.5 . . ?
N4 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
N4 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C8 N1 C27 116.4(2) . . ?
C8 N1 C6 122.8(2) . . ?
C27 N1 C6 118.5(2) . . ?
C7 N2 C10 110.4(2) . . ?
C7 N2 C11 124.1(3) . . ?
C10 N2 C11 125.4(3) . . ?
C16 N3 C24 110.8(2) . . ?
C16 N3 C15' 128.1(5) . . ?
C24 N3 C15' 116.9(4) . . ?
C16 N3 C15 118.1(5) . . ?
C24 N3 C15 130.8(5) . . ?
C28 N4 C25 112.9(2) . . ?
C28 N4 C29 123.1(3) . . ?
C25 N4 C29 123.9(3) . . ?

_refine_diff_density_max         0.565
_refine_diff_density_min         -0.513
_refine_diff_density_rms         0.056




#===============================================
