# Supplementary Information (SI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
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data_20260310a_0m_pl
_database_code_depnum_ccdc_archive 'CCDC 2538770'
loop_
_audit_author_name
_audit_author_address
'Lei Wang'
;Yangzhou university
China
;
_audit_update_record             
;
2026-03-18 deposited with the CCDC.	2026-04-29 downloaded from the CCDC.
;
_audit_creation_date             2026-03-10
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C33 H35 N3 O3'
_chemical_formula_sum            'C33 H35 N3 O3'
_chemical_formula_weight         521.64
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   10.7544(8)
_cell_length_b                   15.4745(11)
_cell_length_c                   17.0735(14)
_cell_angle_alpha                90
_cell_angle_beta                 92.652(3)
_cell_angle_gamma                90
_cell_volume                     2838.3(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3792
_cell_measurement_temperature    100
_cell_measurement_theta_max      22.352
_cell_measurement_theta_min      2.308
_shelx_estimated_absorpt_T_max   0.994
_shelx_estimated_absorpt_T_min   0.991
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_correction_T_min  0.6732
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1426 before and 0.0556 after correction.
The Ratio of minimum to maximum transmission is 0.9033.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.221
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1112
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0470
_diffrn_reflns_av_unetI/netI     0.0676
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            15091
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.703
_diffrn_reflns_theta_min         2.308
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3012
_reflns_number_total             5365
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.174
_refine_diff_density_min         -0.184
_refine_diff_density_rms         0.038
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     358
_refine_ls_number_reflns         5365
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1153
_refine_ls_R_factor_gt           0.0511
_refine_ls_restrained_S_all      1.025
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0644P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1127
_refine_ls_wR_factor_ref         0.1339
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C11(H11), C8(H8), C21(H21), C26(H26), C10(H10), C9(H9), C33(H33),
 C22(H22), C29(H29), C23(H23), C24(H24), C32(H32), C30(H30), C31(H31)
2.c Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C1(H1A,H1B,H1C), C2(H2A,H2B,H2C), C3(H3A,H3B,H3C),
 C18(H18A,H18B,H18C), C19(H19A,H19B,H19C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.17079(12) 0.39721(8) -0.06030(8) 0.0507(4) Uani 1 1 d . . . . .
O2 O 0.31899(14) 0.31117(11) -0.10847(10) 0.0829(5) Uani 1 1 d . . . . .
O3 O 0.25959(17) 0.60879(10) 0.26716(9) 0.0881(6) Uani 1 1 d . . . . .
N3 N 0.38324(14) 0.49816(9) 0.24570(9) 0.0431(4) Uani 1 1 d . . . . .
N1 N 0.35814(14) 0.39308(9) 0.00027(9) 0.0393(4) Uani 1 1 d . . . . .
N2 N 0.44750(15) 0.42434(9) 0.26956(9) 0.0448(4) Uani 1 1 d . . . . .
C13 C 0.42112(18) 0.47261(10) 0.10488(11) 0.0382(5) Uani 1 1 d . . . . .
C6 C 0.32437(19) 0.45455(11) 0.05484(11) 0.0404(5) Uani 1 1 d . . . . .
H6 H 0.244252 0.480163 0.056503 0.048 Uiso 1 1 calc R U . . .
C12 C 0.52440(17) 0.42066(11) 0.08154(11) 0.0387(5) Uani 1 1 d . . . . .
C7 C 0.48296(17) 0.37110(11) 0.01649(11) 0.0391(5) Uani 1 1 d . . . . .
C14 C 0.42072(19) 0.53633(11) 0.17039(11) 0.0451(5) Uani 1 1 d . . . . .
H14A H 0.505107 0.561377 0.178088 0.054 Uiso 1 1 calc R U . . .
H14B H 0.362807 0.583939 0.155566 0.054 Uiso 1 1 calc R U . . .
C20 C 0.56908(19) 0.42612(12) 0.29985(11) 0.0466(5) Uani 1 1 d . . . . .
C11 C 0.64709(19) 0.41310(13) 0.10934(12) 0.0519(6) Uani 1 1 d . . . . .
H11 H 0.677201 0.445789 0.153340 0.062 Uiso 1 1 calc R U . . .
C15 C 0.3088(2) 0.54340(13) 0.29401(12) 0.0524(6) Uani 1 1 d . . . . .
C27 C 0.4171(2) 0.34003(12) 0.24433(12) 0.0492(5) Uani 1 1 d . . . . .
C5 C 0.28301(19) 0.36220(13) -0.06185(13) 0.0495(5) Uani 1 1 d . . . . .
C28 C 0.2994(2) 0.31577(12) 0.20302(12) 0.0507(5) Uani 1 1 d . . . . .
C8 C 0.55983(19) 0.31332(12) -0.02055(12) 0.0485(5) Uani 1 1 d . . . . .
H8 H 0.530221 0.279329 -0.063832 0.058 Uiso 1 1 calc R U . . .
C16 C 0.2872(2) 0.51980(14) 0.38000(13) 0.0588(6) Uani 1 1 d . . . . .
C25 C 0.6126(2) 0.34094(13) 0.29884(13) 0.0544(6) Uani 1 1 d . . . . .
C21 C 0.6410(2) 0.49463(14) 0.32674(12) 0.0561(6) Uani 1 1 d . . . . .
H21 H 0.609146 0.551887 0.326705 0.067 Uiso 1 1 calc R U . . .
C26 C 0.5164(2) 0.28951(13) 0.26405(13) 0.0592(6) Uani 1 1 d . . . . .
H26 H 0.520737 0.228887 0.255816 0.071 Uiso 1 1 calc R U . . .
C10 C 0.7242(2) 0.35743(15) 0.07200(14) 0.0619(6) Uani 1 1 d . . . . .
H10 H 0.808904 0.352724 0.089882 0.074 Uiso 1 1 calc R U . . .
C4 C 0.07284(19) 0.37473(14) -0.12043(12) 0.0548(6) Uani 1 1 d . . . . .
C9 C 0.6810(2) 0.30783(14) 0.00862(13) 0.0584(6) Uani 1 1 d . . . . .
H9 H 0.736455 0.269134 -0.015188 0.070 Uiso 1 1 calc R U . . .
C33 C 0.1852(2) 0.35062(14) 0.21898(14) 0.0616(6) Uani 1 1 d . . . . .
H33 H 0.180586 0.394102 0.258016 0.074 Uiso 1 1 calc R U . . .
C22 C 0.7610(2) 0.47678(16) 0.35365(14) 0.0655(6) Uani 1 1 d . . . . .
H22 H 0.813434 0.522401 0.372383 0.079 Uiso 1 1 calc R U . . .
C29 C 0.3035(3) 0.25268(13) 0.14482(14) 0.0665(7) Uani 1 1 d . . . . .
H29 H 0.380902 0.227851 0.132266 0.080 Uiso 1 1 calc R U . . .
C23 C 0.8061(2) 0.39198(18) 0.35362(15) 0.0764(7) Uani 1 1 d . . . . .
H23 H 0.888879 0.380896 0.372911 0.092 Uiso 1 1 calc R U . . .
C24 C 0.7339(2) 0.32477(17) 0.32647(15) 0.0743(7) Uani 1 1 d . . . . .
H24 H 0.766287 0.267644 0.326482 0.089 Uiso 1 1 calc R U . . .
C32 C 0.0774(2) 0.32335(17) 0.17914(15) 0.0752(7) Uani 1 1 d . . . . .
H32 H -0.000309 0.347882 0.191347 0.090 Uiso 1 1 calc R U . . .
C30 C 0.1942(3) 0.22622(15) 0.10523(15) 0.0824(8) Uani 1 1 d . . . . .
H30 H 0.197566 0.183135 0.065743 0.099 Uiso 1 1 calc R U . . .
C17 C 0.3209(2) 0.42995(15) 0.41120(13) 0.0799(8) Uani 1 1 d . . . . .
H17A H 0.278318 0.386132 0.378354 0.120 Uiso 1 1 calc R U . . .
H17B H 0.294931 0.424515 0.465245 0.120 Uiso 1 1 calc R U . . .
H17C H 0.411130 0.421512 0.410044 0.120 Uiso 1 1 calc R U . . .
C31 C 0.0819(3) 0.26138(18) 0.12235(16) 0.0847(8) Uani 1 1 d . . . . .
H31 H 0.007740 0.242856 0.094982 0.102 Uiso 1 1 calc R U . . .
C1 C 0.0448(2) 0.27906(15) -0.11618(16) 0.0870(8) Uani 1 1 d . . . . .
H1A H 0.119325 0.246028 -0.128023 0.130 Uiso 1 1 calc R U . . .
H1B H -0.022854 0.264714 -0.154427 0.130 Uiso 1 1 calc R U . . .
H1C H 0.019596 0.264497 -0.063345 0.130 Uiso 1 1 calc R U . . .
C2 C 0.1121(2) 0.40138(18) -0.20033(14) 0.0866(8) Uani 1 1 d . . . . .
H2A H 0.132955 0.463025 -0.199862 0.130 Uiso 1 1 calc R U . . .
H2B H 0.043677 0.390767 -0.239085 0.130 Uiso 1 1 calc R U . . .
H2C H 0.185065 0.367716 -0.214112 0.130 Uiso 1 1 calc R U . . .
C3 C -0.0354(2) 0.42804(18) -0.09558(15) 0.0850(8) Uani 1 1 d . . . . .
H3A H -0.055003 0.412628 -0.041860 0.128 Uiso 1 1 calc R U . . .
H3B H -0.107977 0.416762 -0.130929 0.128 Uiso 1 1 calc R U . . .
H3C H -0.013757 0.489488 -0.097749 0.128 Uiso 1 1 calc R U . . .
C18 C 0.3648(3) 0.58528(17) 0.42872(15) 0.0982(9) Uani 1 1 d . . . . .
H18A H 0.453537 0.573507 0.423267 0.147 Uiso 1 1 calc R U . . .
H18B H 0.344972 0.580307 0.483989 0.147 Uiso 1 1 calc R U . . .
H18C H 0.345534 0.643865 0.410065 0.147 Uiso 1 1 calc R U . . .
C19 C 0.1497(3) 0.5357(2) 0.39210(17) 0.1129(11) Uani 1 1 d . . . . .
H19A H 0.128356 0.595163 0.377157 0.169 Uiso 1 1 calc R U . . .
H19B H 0.132699 0.526588 0.447393 0.169 Uiso 1 1 calc R U . . .
H19C H 0.099536 0.495404 0.359527 0.169 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C5 1.324(2) . ?
O1 C4 1.478(2) . ?
O2 C5 1.198(2) . ?
O3 C15 1.221(2) . ?
N3 N2 1.386(2) . ?
N3 C14 1.488(2) . ?
N3 C15 1.369(2) . ?
N1 C6 1.391(2) . ?
N1 C7 1.400(2) . ?
N1 C5 1.388(2) . ?
N2 C20 1.384(3) . ?
N2 C27 1.408(2) . ?
C13 C6 1.345(3) . ?
C13 C12 1.442(2) . ?
C13 C14 1.491(3) . ?
C6 H6 0.9500 . ?
C12 C7 1.405(3) . ?
C12 C11 1.386(3) . ?
C7 C8 1.390(2) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C20 C25 1.399(3) . ?
C20 C21 1.379(3) . ?
C11 H11 0.9500 . ?
C11 C10 1.373(3) . ?
C15 C16 1.541(3) . ?
C27 C28 1.469(3) . ?
C27 C26 1.353(3) . ?
C28 C33 1.380(3) . ?
C28 C29 1.395(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.375(3) . ?
C16 C17 1.527(3) . ?
C16 C18 1.533(3) . ?
C16 C19 1.523(3) . ?
C25 C26 1.415(3) . ?
C25 C24 1.389(3) . ?
C21 H21 0.9500 . ?
C21 C22 1.377(3) . ?
C26 H26 0.9500 . ?
C10 H10 0.9500 . ?
C10 C9 1.389(3) . ?
C4 C1 1.513(3) . ?
C4 C2 1.504(3) . ?
C4 C3 1.504(3) . ?
C9 H9 0.9500 . ?
C33 H33 0.9500 . ?
C33 C32 1.383(3) . ?
C22 H22 0.9500 . ?
C22 C23 1.399(3) . ?
C29 H29 0.9500 . ?
C29 C30 1.390(3) . ?
C23 H23 0.9500 . ?
C23 C24 1.366(3) . ?
C24 H24 0.9500 . ?
C32 H32 0.9500 . ?
C32 C31 1.366(3) . ?
C30 H30 0.9500 . ?
C30 C31 1.369(4) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C31 H31 0.9500 . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 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
C5 O1 C4 120.71(15) . . ?
N2 N3 C14 115.46(14) . . ?
C15 N3 N2 122.82(15) . . ?
C15 N3 C14 120.49(15) . . ?
C6 N1 C7 108.13(16) . . ?
C5 N1 C6 125.89(17) . . ?
C5 N1 C7 125.90(16) . . ?
N3 N2 C27 124.62(17) . . ?
C20 N2 N3 122.88(15) . . ?
C20 N2 C27 109.56(15) . . ?
C6 C13 C12 106.96(16) . . ?
C6 C13 C14 125.79(17) . . ?
C12 C13 C14 127.22(18) . . ?
N1 C6 H6 124.8 . . ?
C13 C6 N1 110.44(17) . . ?
C13 C6 H6 124.8 . . ?
C7 C12 C13 107.61(17) . . ?
C11 C12 C13 133.27(19) . . ?
C11 C12 C7 119.12(17) . . ?
N1 C7 C12 106.85(15) . . ?
C8 C7 N1 130.65(19) . . ?
C8 C7 C12 122.50(18) . . ?
N3 C14 C13 113.33(14) . . ?
N3 C14 H14A 108.9 . . ?
N3 C14 H14B 108.9 . . ?
C13 C14 H14A 108.9 . . ?
C13 C14 H14B 108.9 . . ?
H14A C14 H14B 107.7 . . ?
N2 C20 C25 106.72(18) . . ?
C21 C20 N2 130.22(18) . . ?
C21 C20 C25 123.1(2) . . ?
C12 C11 H11 120.7 . . ?
C10 C11 C12 118.7(2) . . ?
C10 C11 H11 120.7 . . ?
O3 C15 N3 116.93(18) . . ?
O3 C15 C16 118.20(18) . . ?
N3 C15 C16 124.82(18) . . ?
N2 C27 C28 124.51(18) . . ?
C26 C27 N2 106.86(19) . . ?
C26 C27 C28 128.62(19) . . ?
O1 C5 N1 110.04(17) . . ?
O2 C5 O1 127.3(2) . . ?
O2 C5 N1 122.69(19) . . ?
C33 C28 C27 124.1(2) . . ?
C33 C28 C29 118.2(2) . . ?
C29 C28 C27 117.7(2) . . ?
C7 C8 H8 121.7 . . ?
C9 C8 C7 116.6(2) . . ?
C9 C8 H8 121.7 . . ?
C17 C16 C15 120.32(18) . . ?
C17 C16 C18 107.3(2) . . ?
C18 C16 C15 104.98(18) . . ?
C19 C16 C15 106.3(2) . . ?
C19 C16 C17 108.4(2) . . ?
C19 C16 C18 109.1(2) . . ?
C20 C25 C26 107.24(19) . . ?
C24 C25 C20 118.4(2) . . ?
C24 C25 C26 134.3(2) . . ?
C20 C21 H21 121.3 . . ?
C22 C21 C20 117.4(2) . . ?
C22 C21 H21 121.3 . . ?
C27 C26 C25 109.45(18) . . ?
C27 C26 H26 125.3 . . ?
C25 C26 H26 125.3 . . ?
C11 C10 H10 119.3 . . ?
C11 C10 C9 121.4(2) . . ?
C9 C10 H10 119.3 . . ?
O1 C4 C1 109.54(18) . . ?
O1 C4 C2 110.17(16) . . ?
O1 C4 C3 102.18(17) . . ?
C2 C4 C1 112.1(2) . . ?
C3 C4 C1 111.4(2) . . ?
C3 C4 C2 111.0(2) . . ?
C8 C9 C10 121.7(2) . . ?
C8 C9 H9 119.2 . . ?
C10 C9 H9 119.2 . . ?
C28 C33 H33 119.4 . . ?
C28 C33 C32 121.1(2) . . ?
C32 C33 H33 119.4 . . ?
C21 C22 H22 119.7 . . ?
C21 C22 C23 120.5(2) . . ?
C23 C22 H22 119.7 . . ?
C28 C29 H29 120.1 . . ?
C30 C29 C28 119.9(2) . . ?
C30 C29 H29 120.1 . . ?
C22 C23 H23 119.3 . . ?
C24 C23 C22 121.5(2) . . ?
C24 C23 H23 119.3 . . ?
C25 C24 H24 120.4 . . ?
C23 C24 C25 119.2(2) . . ?
C23 C24 H24 120.4 . . ?
C33 C32 H32 119.8 . . ?
C31 C32 C33 120.5(3) . . ?
C31 C32 H32 119.8 . . ?
C29 C30 H30 119.5 . . ?
C31 C30 C29 120.9(2) . . ?
C31 C30 H30 119.5 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C32 C31 C30 119.4(3) . . ?
C32 C31 H31 120.3 . . ?
C30 C31 H31 120.3 . . ?
C4 C1 H1A 109.5 . . ?
C4 C1 H1B 109.5 . . ?
C4 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C4 C2 H2A 109.5 . . ?
C4 C2 H2B 109.5 . . ?
C4 C2 H2C 109.5 . . ?
H2A C2 H2B 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C4 C3 H3A 109.5 . . ?
C4 C3 H3B 109.5 . . ?
C4 C3 H3C 109.5 . . ?
H3A C3 H3B 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C16 C18 H18A 109.5 . . ?
C16 C18 H18B 109.5 . . ?
C16 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C16 C19 H19A 109.5 . . ?
C16 C19 H19B 109.5 . . ?
C16 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O3 C15 C16 C17 166.2(2) . . . . ?
O3 C15 C16 C18 -72.9(3) . . . . ?
O3 C15 C16 C19 42.7(3) . . . . ?
N3 N2 C20 C25 -165.56(16) . . . . ?
N3 N2 C20 C21 14.1(3) . . . . ?
N3 N2 C27 C28 -13.6(3) . . . . ?
N3 N2 C27 C26 165.12(16) . . . . ?
N3 C15 C16 C17 -16.4(3) . . . . ?
N3 C15 C16 C18 104.5(2) . . . . ?
N3 C15 C16 C19 -139.9(2) . . . . ?
N1 C7 C8 C9 178.32(18) . . . . ?
N2 N3 C14 C13 51.7(2) . . . . ?
N2 N3 C15 O3 178.02(19) . . . . ?
N2 N3 C15 C16 0.6(3) . . . . ?
N2 C20 C25 C26 2.6(2) . . . . ?
N2 C20 C25 C24 179.92(18) . . . . ?
N2 C20 C21 C22 -179.73(19) . . . . ?
N2 C27 C28 C33 -37.2(3) . . . . ?
N2 C27 C28 C29 143.75(19) . . . . ?
N2 C27 C26 C25 -2.4(2) . . . . ?
C13 C12 C7 N1 0.59(19) . . . . ?
C13 C12 C7 C8 -179.72(16) . . . . ?
C13 C12 C11 C10 -178.65(19) . . . . ?
C6 N1 C7 C12 -0.31(18) . . . . ?
C6 N1 C7 C8 -179.97(18) . . . . ?
C6 N1 C5 O1 -2.6(3) . . . . ?
C6 N1 C5 O2 177.48(18) . . . . ?
C6 C13 C12 C7 -0.66(19) . . . . ?
C6 C13 C12 C11 178.29(19) . . . . ?
C6 C13 C14 N3 90.2(2) . . . . ?
C12 C13 C6 N1 0.47(19) . . . . ?
C12 C13 C14 N3 -91.6(2) . . . . ?
C12 C7 C8 C9 -1.3(3) . . . . ?
C12 C11 C10 C9 -1.4(3) . . . . ?
C7 N1 C6 C13 -0.11(19) . . . . ?
C7 N1 C5 O1 -179.10(15) . . . . ?
C7 N1 C5 O2 1.0(3) . . . . ?
C7 C12 C11 C10 0.2(3) . . . . ?
C7 C8 C9 C10 0.1(3) . . . . ?
C14 N3 N2 C20 74.1(2) . . . . ?
C14 N3 N2 C27 -84.4(2) . . . . ?
C14 N3 C15 O3 11.3(3) . . . . ?
C14 N3 C15 C16 -166.12(19) . . . . ?
C14 C13 C6 N1 178.95(15) . . . . ?
C14 C13 C12 C7 -179.10(16) . . . . ?
C14 C13 C12 C11 -0.2(3) . . . . ?
C20 N2 C27 C28 -174.59(17) . . . . ?
C20 N2 C27 C26 4.1(2) . . . . ?
C20 C25 C26 C27 -0.1(2) . . . . ?
C20 C25 C24 C23 0.1(3) . . . . ?
C20 C21 C22 C23 -0.3(3) . . . . ?
C11 C12 C7 N1 -178.54(15) . . . . ?
C11 C12 C7 C8 1.2(3) . . . . ?
C11 C10 C9 C8 1.2(3) . . . . ?
C15 N3 N2 C20 -93.2(2) . . . . ?
C15 N3 N2 C27 108.2(2) . . . . ?
C15 N3 C14 C13 -140.60(19) . . . . ?
C27 N2 C20 C25 -4.2(2) . . . . ?
C27 N2 C20 C21 175.5(2) . . . . ?
C27 C28 C33 C32 -178.40(19) . . . . ?
C27 C28 C29 C30 178.64(19) . . . . ?
C5 O1 C4 C1 61.6(2) . . . . ?
C5 O1 C4 C2 -62.2(2) . . . . ?
C5 O1 C4 C3 179.73(18) . . . . ?
C5 N1 C6 C13 -177.11(16) . . . . ?
C5 N1 C7 C12 176.69(16) . . . . ?
C5 N1 C7 C8 -3.0(3) . . . . ?
C28 C27 C26 C25 176.24(19) . . . . ?
C28 C33 C32 C31 -0.5(4) . . . . ?
C28 C29 C30 C31 0.2(4) . . . . ?
C25 C20 C21 C22 -0.1(3) . . . . ?
C21 C20 C25 C26 -177.08(19) . . . . ?
C21 C20 C25 C24 0.2(3) . . . . ?
C21 C22 C23 C24 0.6(4) . . . . ?
C26 C27 C28 C33 144.4(2) . . . . ?
C26 C27 C28 C29 -34.7(3) . . . . ?
C26 C25 C24 C23 176.5(2) . . . . ?
C4 O1 C5 O2 0.0(3) . . . . ?
C4 O1 C5 N1 -179.91(15) . . . . ?
C33 C28 C29 C30 -0.5(3) . . . . ?
C33 C32 C31 C30 0.1(4) . . . . ?
C22 C23 C24 C25 -0.5(4) . . . . ?
C29 C28 C33 C32 0.7(3) . . . . ?
C29 C30 C31 C32 0.0(4) . . . . ?
C24 C25 C26 C27 -176.8(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_123_a
_database_code_depnum_ccdc_archive 'CCDC 2548831'
loop_
_audit_author_name
_audit_author_address
'Lei Wang'
;Yangzhou university
China
;
_audit_update_record             
;
2026-04-23 deposited with the CCDC.	2026-04-29 downloaded from the CCDC.
;
_audit_creation_date             2026-04-21
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C30 H34 Cl N3 O5'
_chemical_formula_sum            'C30 H34 Cl N3 O5'
_chemical_formula_weight         552.05
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   20.503(2)
_cell_length_b                   16.785(2)
_cell_length_c                   17.144(2)
_cell_angle_alpha                90
_cell_angle_beta                 94.575(5)
_cell_angle_gamma                90
_cell_volume                     5881.2(12)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9886
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      24.38
_cell_measurement_theta_min      2.38
_shelx_estimated_absorpt_T_max   0.983
_shelx_estimated_absorpt_T_min   0.978
_exptl_absorpt_coefficient_mu    0.172
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6811
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1062 before and 0.0484 after correction.
The Ratio of minimum to maximum transmission is 0.9136.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.247
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             2336
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0510
_diffrn_reflns_av_unetI/netI     0.0414
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            45160
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.514
_diffrn_reflns_theta_min         2.384
_diffrn_ambient_temperature      273.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4263
_reflns_number_total             6758
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         0.145
_refine_diff_density_min         -0.197
_refine_diff_density_rms         0.035
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     390
_refine_ls_number_reflns         6758
_refine_ls_number_restraints     63
_refine_ls_R_factor_all          0.0999
_refine_ls_R_factor_gt           0.0531
_refine_ls_restrained_S_all      1.008
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0462P)²+3.8547P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1061
_refine_ls_wR_factor_ref         0.1239
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C13-C14 \\sim C13-C14A
 with sigma of 0.02
 C13-C16 \\sim C13-C16A
 with sigma of 0.02
 C13-C15 \\sim C13-C15A
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
C16 \\sim C13 \\sim C15 \\sim C14 \\sim C12: within 2A with sigma of 0.01 and
sigma for terminal atoms of 0.02 within 2A
C13 \\sim C14 \\sim C16 \\sim C15 \\sim C14A \\sim C16A \\sim C15A: within 2A
with sigma of 0.01 and sigma for terminal atoms of 0.02 within 2A
4. Rigid body (RIGU) restrains
 C16A, C16, C15A, C15, C14, C14A
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
5. Others
 Sof(C14A)=Sof(H14D)=Sof(H14E)=Sof(H14F)=Sof(C16A)=Sof(H16D)=Sof(H16E)=
 Sof(H16F)=Sof(C15A)=Sof(H15D)=Sof(H15E)=Sof(H15F)=1-FVAR(1)
 Sof(C14)=Sof(H14A)=Sof(H14B)=Sof(H14C)=Sof(C16)=Sof(H16A)=Sof(H16B)=Sof(H16C)=
 Sof(C15)=Sof(H15A)=Sof(H15B)=Sof(H15C)=FVAR(1)
6.a Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B), C10(H10A,H10B)
6.b Aromatic/amide H refined with riding coordinates:
 C25(H25), C7(H7), C23(H23), C22(H22), C21(H21), C20(H20), C1(H1), C3(H3),
 C4(H4)
6.c Idealised Me refined as rotating group:
 C30(H30A,H30B,H30C), C11(H11A,H11B,H11C), C28(H28A,H28B,H28C), C29(H29A,H29B,
 H29C), C14(H14A,H14B,H14C), C16(H16A,H16B,H16C), C15(H15A,H15B,H15C),
 C14A(H14D,H14E,H14F), C16A(H16D,H16E,H16F), C15A(H15D,H15E,H15F)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.63229(3) 0.33726(4) 0.45389(3) 0.0762(2) Uani 1 1 d . . . . .
O5 O 0.49674(7) 0.22308(9) 0.61845(8) 0.0633(4) Uani 1 1 d . . . . .
O1 O 0.77453(7) 0.13672(7) 0.88495(7) 0.0548(4) Uani 1 1 d . . . . .
O4 O 0.44887(7) 0.33067(9) 0.55844(9) 0.0742(5) Uani 1 1 d . . . . .
O3 O 0.77061(7) 0.46373(8) 0.83183(9) 0.0697(4) Uani 1 1 d . . . . .
O2 O 0.79168(8) 0.26789(8) 0.89650(9) 0.0738(5) Uani 1 1 d . . . . .
N3 N 0.53129(7) 0.34411(9) 0.65441(8) 0.0450(4) Uani 1 1 d . . . . .
N2 N 0.72848(7) 0.35746(8) 0.76976(8) 0.0411(3) Uani 1 1 d . . . . .
N1 N 0.73694(7) 0.28405(8) 0.73474(8) 0.0421(4) Uani 1 1 d . . . . .
C30 C 0.38956(11) 0.16597(15) 0.57773(17) 0.0854(8) Uani 1 1 d . . . . .
H30A H 0.382447 0.161915 0.632263 0.128 Uiso 1 1 calc R U . . .
H30B H 0.368189 0.122449 0.549788 0.128 Uiso 1 1 calc R U . . .
H30C H 0.371959 0.215439 0.557377 0.128 Uiso 1 1 calc R U . . .
C27 C 0.46188(11) 0.16297(13) 0.56796(14) 0.0663(6) Uani 1 1 d . . . . .
C26 C 0.48782(9) 0.30036(13) 0.60494(11) 0.0527(5) Uani 1 1 d . . . . .
C25 C 0.57528(8) 0.31346(12) 0.71312(10) 0.0448(4) Uani 1 1 d . . . . .
H25 H 0.579840 0.259784 0.725836 0.054 Uiso 1 1 calc R U . . .
C18 C 0.61005(8) 0.37281(11) 0.74855(10) 0.0428(4) Uani 1 1 d . . . . .
C17 C 0.66688(9) 0.36438(12) 0.80816(10) 0.0475(4) Uani 1 1 d . . . . .
H17A H 0.669018 0.410422 0.842469 0.057 Uiso 1 1 calc R U . . .
H17B H 0.660999 0.317394 0.839783 0.057 Uiso 1 1 calc R U . . .
C8 C 0.74923(8) 0.21263(10) 0.77550(10) 0.0437(4) Uani 1 1 d . . . . .
C9 C 0.77399(9) 0.21072(11) 0.85808(11) 0.0489(5) Uani 1 1 d . . . . .
C10 C 0.80171(12) 0.12515(12) 0.96518(12) 0.0648(6) Uani 1 1 d . . . . .
H10A H 0.773564 0.149375 1.001387 0.078 Uiso 1 1 calc R U . . .
H10B H 0.844673 0.149437 0.972798 0.078 Uiso 1 1 calc R U . . .
C11 C 0.80640(16) 0.03805(14) 0.97889(14) 0.0909(9) Uani 1 1 d . . . . .
H11A H 0.763283 0.015373 0.975429 0.136 Uiso 1 1 calc R U . . .
H11B H 0.827478 0.028197 1.030003 0.136 Uiso 1 1 calc R U . . .
H11C H 0.831485 0.014177 0.940105 0.136 Uiso 1 1 calc R U . . .
C7 C 0.73782(9) 0.15138(11) 0.72507(11) 0.0496(5) Uani 1 1 d . . . . .
H7 H 0.743961 0.097680 0.736813 0.060 Uiso 1 1 calc R U . . .
C5 C 0.71488(9) 0.18301(11) 0.65114(11) 0.0465(4) Uani 1 1 d . . . . .
C6 C 0.71284(8) 0.26606(10) 0.65910(10) 0.0418(4) Uani 1 1 d . . . . .
C28 C 0.47674(16) 0.1764(2) 0.48385(17) 0.1093(10) Uani 1 1 d . . . . .
H28A H 0.454246 0.223154 0.463898 0.164 Uiso 1 1 calc R U . . .
H28B H 0.462385 0.131071 0.452870 0.164 Uiso 1 1 calc R U . . .
H28C H 0.523011 0.183329 0.481466 0.164 Uiso 1 1 calc R U . . .
C29 C 0.49214(14) 0.08666(16) 0.6002(2) 0.1077(11) Uani 1 1 d . . . . .
H29A H 0.538257 0.087034 0.594006 0.162 Uiso 1 1 calc R U . . .
H29B H 0.472239 0.042098 0.572475 0.162 Uiso 1 1 calc R U . . .
H29C H 0.485182 0.082291 0.654797 0.162 Uiso 1 1 calc R U . . .
C24 C 0.53830(8) 0.42728(11) 0.65391(11) 0.0470(5) Uani 1 1 d . . . . .
C23 C 0.50635(10) 0.48523(14) 0.60778(13) 0.0630(6) Uani 1 1 d . . . . .
H23 H 0.473710 0.472247 0.569074 0.076 Uiso 1 1 calc R U . . .
C22 C 0.52513(12) 0.56270(14) 0.62187(16) 0.0776(7) Uani 1 1 d . . . . .
H22 H 0.505166 0.602921 0.591227 0.093 Uiso 1 1 calc R U . . .
C21 C 0.57280(12) 0.58293(14) 0.68016(16) 0.0764(7) Uani 1 1 d . . . . .
H21 H 0.583501 0.636239 0.688617 0.092 Uiso 1 1 calc R U . . .
C20 C 0.60449(11) 0.52545(12) 0.72566(13) 0.0614(5) Uani 1 1 d . . . . .
H20 H 0.636756 0.539167 0.764555 0.074 Uiso 1 1 calc R U . . .
C19 C 0.58728(8) 0.44618(11) 0.71233(10) 0.0455(4) Uani 1 1 d . . . . .
C12 C 0.78004(9) 0.40853(10) 0.78862(11) 0.0458(4) Uani 1 1 d . U . . .
C13 C 0.84454(9) 0.40325(12) 0.74898(12) 0.0549(5) Uani 1 1 d D U . . .
C14 C 0.8287(5) 0.4410(6) 0.6675(3) 0.0679(17) Uani 0.75(3) 1 d D U P A 1
H14A H 0.799863 0.406527 0.636249 0.102 Uiso 0.75(3) 1 calc R U P A 1
H14B H 0.868442 0.448360 0.642400 0.102 Uiso 0.75(3) 1 calc R U P A 1
H14C H 0.807869 0.491680 0.673340 0.102 Uiso 0.75(3) 1 calc R U P A 1
C16 C 0.8794(5) 0.3227(4) 0.7522(9) 0.092(3) Uani 0.75(3) 1 d D U P A 1
H16A H 0.885254 0.304788 0.805476 0.138 Uiso 0.75(3) 1 calc R U P A 1
H16B H 0.921320 0.328028 0.731487 0.138 Uiso 0.75(3) 1 calc R U P A 1
H16C H 0.853494 0.284549 0.721603 0.138 Uiso 0.75(3) 1 calc R U P A 1
C15 C 0.8914(4) 0.4644(5) 0.7908(5) 0.0721(17) Uani 0.75(3) 1 d D U P A 1
H15A H 0.873402 0.516910 0.783809 0.108 Uiso 0.75(3) 1 calc R U P A 1
H15B H 0.933087 0.462111 0.769000 0.108 Uiso 0.75(3) 1 calc R U P A 1
H15C H 0.896971 0.452128 0.845632 0.108 Uiso 0.75(3) 1 calc R U P A 1
C1 C 0.68832(8) 0.31605(12) 0.59919(10) 0.0458(4) Uani 1 1 d . . . . .
H1 H 0.686844 0.371067 0.605246 0.055 Uiso 1 1 calc R U . . .
C2 C 0.66642(9) 0.27933(13) 0.53051(11) 0.0515(5) Uani 1 1 d . . . . .
C3 C 0.66925(10) 0.19689(14) 0.51996(12) 0.0592(6) Uani 1 1 d . . . . .
H3 H 0.654558 0.174781 0.472007 0.071 Uiso 1 1 calc R U . . .
C4 C 0.69325(10) 0.14883(13) 0.57909(12) 0.0567(5) Uani 1 1 d . . . . .
H4 H 0.695311 0.093996 0.571906 0.068 Uiso 1 1 calc R U . . .
C14A C 0.8373(16) 0.417(2) 0.6623(9) 0.076(5) Uani 0.25(3) 1 d D U P A 2
H14D H 0.808849 0.377750 0.637736 0.114 Uiso 0.25(3) 1 calc R U P A 2
H14E H 0.879443 0.414178 0.641775 0.114 Uiso 0.25(3) 1 calc R U P A 2
H14F H 0.819001 0.469331 0.651943 0.114 Uiso 0.25(3) 1 calc R U P A 2
C16A C 0.8682(13) 0.3192(10) 0.7259(15) 0.066(5) Uani 0.25(3) 1 d D U P A 2
H16D H 0.868607 0.284445 0.770374 0.099 Uiso 0.25(3) 1 calc R U P A 2
H16E H 0.911540 0.323030 0.708781 0.099 Uiso 0.25(3) 1 calc R U P A 2
H16F H 0.839057 0.298313 0.684271 0.099 Uiso 0.25(3) 1 calc R U P A 2
C15A C 0.8976(15) 0.442(2) 0.8052(19) 0.100(6) Uani 0.25(3) 1 d D U P A 2
H15D H 0.882516 0.493137 0.821696 0.149 Uiso 0.25(3) 1 calc R U P A 2
H15E H 0.936865 0.449030 0.778933 0.149 Uiso 0.25(3) 1 calc R U P A 2
H15F H 0.906587 0.408577 0.850140 0.149 Uiso 0.25(3) 1 calc R U P A 2


_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
Cl1 C2 1.736(2) . ?
O5 C27 1.476(2) . ?
O5 C26 1.328(2) . ?
O1 C9 1.325(2) . ?
O1 C10 1.455(2) . ?
O4 C26 1.196(2) . ?
O3 C12 1.211(2) . ?
O2 C9 1.203(2) . ?
N3 C26 1.390(2) . ?
N3 C25 1.395(2) . ?
N3 C24 1.404(2) . ?
N2 N1 1.3877(19) . ?
N2 C17 1.475(2) . ?
N2 C12 1.379(2) . ?
N1 C8 1.400(2) . ?
N1 C6 1.384(2) . ?
C30 H30A 0.9600 . ?
C30 H30B 0.9600 . ?
C30 H30C 0.9600 . ?
C30 C27 1.506(3) . ?
C27 C28 1.514(4) . ?
C27 C29 1.509(3) . ?
C25 H25 0.9300 . ?
C25 C18 1.342(2) . ?
C18 C17 1.494(2) . ?
C18 C19 1.440(3) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C8 C9 1.466(3) . ?
C8 C7 1.351(2) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C11 1.483(3) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C7 H7 0.9300 . ?
C7 C5 1.419(3) . ?
C5 C6 1.402(3) . ?
C5 C4 1.402(2) . ?
C6 C1 1.389(2) . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?
C29 H29A 0.9600 . ?
C29 H29B 0.9600 . ?
C29 H29C 0.9600 . ?
C24 C23 1.385(3) . ?
C24 C19 1.397(2) . ?
C23 H23 0.9300 . ?
C23 C22 1.372(3) . ?
C22 H22 0.9300 . ?
C22 C21 1.383(3) . ?
C21 H21 0.9300 . ?
C21 C20 1.371(3) . ?
C20 H20 0.9300 . ?
C20 C19 1.391(3) . ?
C12 C13 1.537(3) . ?
C13 C14 1.544(5) . ?
C13 C16 1.529(6) . ?
C13 C15 1.543(5) . ?
C13 C14A 1.500(15) . ?
C13 C16A 1.553(15) . ?
C13 C15A 1.541(15) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C1 H1 0.9300 . ?
C1 C2 1.372(2) . ?
C2 C3 1.397(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.357(3) . ?
C4 H4 0.9300 . ?
C14A H14D 0.9600 . ?
C14A H14E 0.9600 . ?
C14A H14F 0.9600 . ?
C16A H16D 0.9600 . ?
C16A H16E 0.9600 . ?
C16A H16F 0.9600 . ?
C15A H15D 0.9600 . ?
C15A H15E 0.9600 . ?
C15A H15F 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
C26 O5 C27 120.79(15) . . ?
C9 O1 C10 116.48(14) . . ?
C26 N3 C25 126.27(16) . . ?
C26 N3 C24 125.64(16) . . ?
C25 N3 C24 108.09(15) . . ?
N1 N2 C17 113.84(14) . . ?
C12 N2 N1 122.23(15) . . ?
C12 N2 C17 120.94(15) . . ?
N2 N1 C8 124.62(14) . . ?
C6 N1 N2 123.48(14) . . ?
C6 N1 C8 108.51(13) . . ?
H30A C30 H30B 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C27 C30 H30A 109.5 . . ?
C27 C30 H30B 109.5 . . ?
C27 C30 H30C 109.5 . . ?
O5 C27 C30 110.30(19) . . ?
O5 C27 C28 109.4(2) . . ?
O5 C27 C29 101.50(17) . . ?
C30 C27 C28 112.1(2) . . ?
C30 C27 C29 111.5(2) . . ?
C29 C27 C28 111.5(2) . . ?
O5 C26 N3 109.69(16) . . ?
O4 C26 O5 127.39(19) . . ?
O4 C26 N3 122.9(2) . . ?
N3 C25 H25 125.0 . . ?
C18 C25 N3 110.02(16) . . ?
C18 C25 H25 125.0 . . ?
C25 C18 C17 126.62(17) . . ?
C25 C18 C19 107.30(15) . . ?
C19 C18 C17 125.75(16) . . ?
N2 C17 C18 110.55(14) . . ?
N2 C17 H17A 109.5 . . ?
N2 C17 H17B 109.5 . . ?
C18 C17 H17A 109.5 . . ?
C18 C17 H17B 109.5 . . ?
H17A C17 H17B 108.1 . . ?
N1 C8 C9 122.37(15) . . ?
C7 C8 N1 108.48(15) . . ?
C7 C8 C9 129.06(17) . . ?
O1 C9 C8 110.43(15) . . ?
O2 C9 O1 124.31(17) . . ?
O2 C9 C8 125.26(18) . . ?
O1 C10 H10A 110.3 . . ?
O1 C10 H10B 110.3 . . ?
O1 C10 C11 107.25(16) . . ?
H10A C10 H10B 108.5 . . ?
C11 C10 H10A 110.3 . . ?
C11 C10 H10B 110.3 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C8 C7 H7 125.8 . . ?
C8 C7 C5 108.35(16) . . ?
C5 C7 H7 125.8 . . ?
C6 C5 C7 107.19(15) . . ?
C6 C5 C4 118.89(18) . . ?
C4 C5 C7 133.86(19) . . ?
N1 C6 C5 107.28(15) . . ?
N1 C6 C1 129.96(16) . . ?
C1 C6 C5 122.74(16) . . ?
C27 C28 H28A 109.5 . . ?
C27 C28 H28B 109.5 . . ?
C27 C28 H28C 109.5 . . ?
H28A C28 H28B 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C27 C29 H29A 109.5 . . ?
C27 C29 H29B 109.5 . . ?
C27 C29 H29C 109.5 . . ?
H29A C29 H29B 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C23 C24 N3 131.16(18) . . ?
C23 C24 C19 122.01(19) . . ?
C19 C24 N3 106.83(15) . . ?
C24 C23 H23 121.6 . . ?
C22 C23 C24 116.9(2) . . ?
C22 C23 H23 121.6 . . ?
C23 C22 H22 118.9 . . ?
C23 C22 C21 122.1(2) . . ?
C21 C22 H22 118.9 . . ?
C22 C21 H21 119.5 . . ?
C20 C21 C22 120.9(2) . . ?
C20 C21 H21 119.5 . . ?
C21 C20 H20 120.8 . . ?
C21 C20 C19 118.5(2) . . ?
C19 C20 H20 120.8 . . ?
C24 C19 C18 107.75(16) . . ?
C20 C19 C18 132.68(18) . . ?
C20 C19 C24 119.57(18) . . ?
O3 C12 N2 117.51(18) . . ?
O3 C12 C13 119.97(17) . . ?
N2 C12 C13 122.07(16) . . ?
C12 C13 C14 104.4(4) . . ?
C12 C13 C15 106.4(4) . . ?
C12 C13 C16A 117.5(10) . . ?
C12 C13 C15A 106.8(15) . . ?
C16 C13 C12 116.8(4) . . ?
C16 C13 C14 117.4(9) . . ?
C16 C13 C15 107.4(5) . . ?
C15 C13 C14 103.0(6) . . ?
C14A C13 C12 114.1(13) . . ?
C14A C13 C16A 84.2(19) . . ?
C14A C13 C15A 124(2) . . ?
C15A C13 C16A 109.0(15) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C6 C1 H1 122.0 . . ?
C2 C1 C6 115.94(18) . . ?
C2 C1 H1 122.0 . . ?
C1 C2 Cl1 118.83(16) . . ?
C1 C2 C3 122.80(19) . . ?
C3 C2 Cl1 118.37(15) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 C2 120.57(18) . . ?
C4 C3 H3 119.7 . . ?
C5 C4 H4 120.5 . . ?
C3 C4 C5 119.04(19) . . ?
C3 C4 H4 120.5 . . ?
C13 C14A H14D 109.5 . . ?
C13 C14A H14E 109.5 . . ?
C13 C14A H14F 109.5 . . ?
H14D C14A H14E 109.5 . . ?
H14D C14A H14F 109.5 . . ?
H14E C14A H14F 109.5 . . ?
C13 C16A H16D 109.5 . . ?
C13 C16A H16E 109.5 . . ?
C13 C16A H16F 109.5 . . ?
H16D C16A H16E 109.5 . . ?
H16D C16A H16F 109.5 . . ?
H16E C16A H16F 109.5 . . ?
C13 C15A H15D 109.5 . . ?
C13 C15A H15E 109.5 . . ?
C13 C15A H15F 109.5 . . ?
H15D C15A H15E 109.5 . . ?
H15D C15A H15F 109.5 . . ?
H15E C15A H15F 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cl1 C2 C3 C4 -177.55(16) . . . . ?
O3 C12 C13 C14 -95.6(4) . . . . ?
O3 C12 C13 C16 132.9(7) . . . . ?
O3 C12 C13 C15 13.0(4) . . . . ?
O3 C12 C13 C14A -110.2(14) . . . . ?
O3 C12 C13 C16A 153.6(11) . . . . ?
O3 C12 C13 C15A 30.9(16) . . . . ?
N3 C25 C18 C17 -172.85(16) . . . . ?
N3 C25 C18 C19 0.9(2) . . . . ?
N3 C24 C23 C22 -179.6(2) . . . . ?
N3 C24 C19 C18 -0.02(19) . . . . ?
N3 C24 C19 C20 -179.53(16) . . . . ?
N2 N1 C8 C9 -19.0(3) . . . . ?
N2 N1 C8 C7 164.17(16) . . . . ?
N2 N1 C6 C5 -164.42(15) . . . . ?
N2 N1 C6 C1 13.7(3) . . . . ?
N2 C12 C13 C14 76.5(4) . . . . ?
N2 C12 C13 C16 -55.0(7) . . . . ?
N2 C12 C13 C15 -174.9(4) . . . . ?
N2 C12 C13 C14A 61.9(14) . . . . ?
N2 C12 C13 C16A -34.3(12) . . . . ?
N2 C12 C13 C15A -157.0(16) . . . . ?
N1 N2 C17 C18 -73.99(18) . . . . ?
N1 N2 C12 O3 -166.32(16) . . . . ?
N1 N2 C12 C13 21.4(2) . . . . ?
N1 C8 C9 O1 173.06(16) . . . . ?
N1 C8 C9 O2 -7.2(3) . . . . ?
N1 C8 C7 C5 -2.7(2) . . . . ?
N1 C6 C1 C2 -178.43(17) . . . . ?
C27 O5 C26 O4 7.2(3) . . . . ?
C27 O5 C26 N3 -173.23(17) . . . . ?
C26 O5 C27 C30 -67.1(3) . . . . ?
C26 O5 C27 C28 56.6(3) . . . . ?
C26 O5 C27 C29 174.6(2) . . . . ?
C26 N3 C25 C18 179.26(17) . . . . ?
C26 N3 C24 C23 0.2(3) . . . . ?
C26 N3 C24 C19 -179.63(17) . . . . ?
C25 N3 C26 O5 -3.7(3) . . . . ?
C25 N3 C26 O4 175.90(19) . . . . ?
C25 N3 C24 C23 -179.7(2) . . . . ?
C25 N3 C24 C19 0.54(19) . . . . ?
C25 C18 C17 N2 87.9(2) . . . . ?
C25 C18 C19 C24 -0.5(2) . . . . ?
C25 C18 C19 C20 178.9(2) . . . . ?
C17 N2 N1 C8 -69.9(2) . . . . ?
C17 N2 N1 C6 86.85(19) . . . . ?
C17 N2 C12 O3 -7.1(2) . . . . ?
C17 N2 C12 C13 -179.38(16) . . . . ?
C17 C18 C19 C24 173.26(17) . . . . ?
C17 C18 C19 C20 -7.3(3) . . . . ?
C8 N1 C6 C5 -4.43(19) . . . . ?
C8 N1 C6 C1 173.68(18) . . . . ?
C8 C7 C5 C6 -0.1(2) . . . . ?
C8 C7 C5 C4 -177.1(2) . . . . ?
C9 O1 C10 C11 -171.9(2) . . . . ?
C9 C8 C7 C5 -179.16(18) . . . . ?
C10 O1 C9 O2 -3.3(3) . . . . ?
C10 O1 C9 C8 176.44(17) . . . . ?
C7 C8 C9 O1 -10.9(3) . . . . ?
C7 C8 C9 O2 168.9(2) . . . . ?
C7 C5 C6 N1 2.8(2) . . . . ?
C7 C5 C6 C1 -175.49(16) . . . . ?
C7 C5 C4 C3 174.9(2) . . . . ?
C5 C6 C1 C2 -0.6(3) . . . . ?
C6 N1 C8 C9 -178.75(16) . . . . ?
C6 N1 C8 C7 4.5(2) . . . . ?
C6 C5 C4 C3 -1.9(3) . . . . ?
C6 C1 C2 Cl1 177.69(13) . . . . ?
C6 C1 C2 C3 -1.1(3) . . . . ?
C24 N3 C26 O5 176.49(16) . . . . ?
C24 N3 C26 O4 -3.9(3) . . . . ?
C24 N3 C25 C18 -0.9(2) . . . . ?
C24 C23 C22 C21 -1.2(4) . . . . ?
C23 C24 C19 C18 -179.84(17) . . . . ?
C23 C24 C19 C20 0.7(3) . . . . ?
C23 C22 C21 C20 1.4(4) . . . . ?
C22 C21 C20 C19 -0.5(4) . . . . ?
C21 C20 C19 C18 -179.8(2) . . . . ?
C21 C20 C19 C24 -0.5(3) . . . . ?
C19 C18 C17 N2 -84.7(2) . . . . ?
C19 C24 C23 C22 0.2(3) . . . . ?
C12 N2 N1 C8 90.7(2) . . . . ?
C12 N2 N1 C6 -112.57(19) . . . . ?
C12 N2 C17 C18 125.15(17) . . . . ?
C1 C2 C3 C4 1.2(3) . . . . ?
C2 C3 C4 C5 0.3(3) . . . . ?
C4 C5 C6 N1 -179.67(16) . . . . ?
C4 C5 C6 C1 2.1(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
