# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
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data_1
_database_code_depnum_ccdc_archive 'CCDC 2305863'
loop_
_audit_author_name
_audit_author_address
'Hui Xu'
;Anuhui Polytechnic University
China
;
_audit_update_record             
;
2023-11-06 deposited with the CCDC.	2024-03-12 downloaded from the CCDC.
;
_audit_creation_date             2021-08-11
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C26 H26 Cl N3 O5'
_chemical_formula_sum            'C26 H26 Cl N3 O5'
_chemical_formula_weight         495.95
_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.2719(11)
_cell_length_b                   10.9748(14)
_cell_length_c                   14.3779(18)
_cell_angle_alpha                91.073(2)
_cell_angle_beta                 98.225(2)
_cell_angle_gamma                110.945(2)
_cell_volume                     1203.0(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2347
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.51
_cell_measurement_theta_min      2.37
_shelx_estimated_absorpt_T_max   0.959
_shelx_estimated_absorpt_T_min   0.949
_exptl_absorpt_coefficient_mu    0.202
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            COLORLESS
_exptl_crystal_density_diffrn    1.369
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.21
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0147
_diffrn_reflns_av_unetI/netI     0.0323
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            6128
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        24.998
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_min         2.543
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3112
_reflns_number_total             4196
_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       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.534
_refine_diff_density_min         -0.412
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     319
_refine_ls_number_reflns         4196
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0686
_refine_ls_R_factor_gt           0.0474
_refine_ls_restrained_S_all      1.057
_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)+(0.0659P)²+0.2610P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1220
_refine_ls_wR_factor_ref         0.1297
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Rigid bond restraints
 C19, C20
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.001
3.a Ternary CH refined with riding coordinates:
 C13(H13)
3.b Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C7(H7A,H7B), C11(H11A,H11B)
3.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C17(H17), C20(H20), C5(H5), C1(H1A), C19(H19), C18(H18), C2(H2),
 C4(H4), C3(H3)
3.d Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C), C12(H12A,H12B,H12C), C25(H25A,H25B,H25C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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 0.75339(11) 0.39010(8) 0.03676(4) 0.0718(3) Uani 1 1 d . . . . .
O2 O 0.4289(2) 0.09380(14) 0.15039(11) 0.0486(4) Uani 1 1 d . . . . .
O3 O 1.0461(2) 0.51311(15) 0.37653(10) 0.0430(4) Uani 1 1 d . . . . .
O1 O 0.3609(2) -0.00067(15) 0.28468(12) 0.0556(5) Uani 1 1 d . . . . .
O4 O 0.8940(2) 0.72588(17) 0.13429(12) 0.0602(5) Uani 1 1 d . . . . .
N2 N 0.9701(2) 0.60675(16) 0.24726(12) 0.0343(4) Uani 1 1 d . . . . .
O5 O 0.4847(2) 0.50402(17) 0.30895(13) 0.0559(5) Uani 1 1 d . . . . .
N3 N 0.6835(3) 0.61058(19) 0.21768(13) 0.0444(5) Uani 1 1 d . . . . .
N1 N 0.5087(3) 0.16802(19) 0.44859(13) 0.0504(5) Uani 1 1 d . . . . .
H1 H 0.4585 0.0863 0.4304 0.060 Uiso 1 1 calc R . . . .
C22 C 0.9318(3) 0.52551(19) 0.31968(14) 0.0313(5) Uani 1 1 d . . . . .
C13 C 0.6779(3) 0.32369(19) 0.23928(14) 0.0329(5) Uani 1 1 d . . . . .
H13 H 0.6031 0.3389 0.1850 0.040 Uiso 1 1 calc R . . . .
C16 C 0.8300(3) 0.29823(19) 0.20515(14) 0.0338(5) Uani 1 1 d . . . . .
C14 C 0.7389(3) 0.44657(19) 0.31653(14) 0.0321(5) Uani 1 1 d . . . . .
C9 C 0.5673(3) 0.2148(2) 0.29107(15) 0.0349(5) Uani 1 1 d . . . . .
C8 C 0.5840(3) 0.2479(2) 0.38482(15) 0.0366(5) Uani 1 1 d . . . . .
C26 C 0.6252(3) 0.5238(2) 0.28453(15) 0.0389(5) Uani 1 1 d . . . . .
C24 C 0.8519(3) 0.6516(2) 0.19507(16) 0.0412(5) Uani 1 1 d . . . . .
C10 C 0.4457(3) 0.0932(2) 0.24459(16) 0.0389(5) Uani 1 1 d . . . . .
C15 C 0.6983(3) 0.3878(2) 0.41059(14) 0.0393(5) Uani 1 1 d . . . . .
H15A H 0.8055 0.3944 0.4515 0.047 Uiso 1 1 calc R . . . .
H15B H 0.6378 0.4329 0.4426 0.047 Uiso 1 1 calc R . . . .
C6 C 0.3201(3) 0.1896(2) 0.55990(15) 0.0409(5) Uani 1 1 d . . . . .
C17 C 0.9345(3) 0.2465(2) 0.26329(17) 0.0454(6) Uani 1 1 d . . . . .
H17 H 0.9040 0.2205 0.3215 0.054 Uiso 1 1 calc R . . . .
C21 C 0.8773(3) 0.3296(2) 0.11743(15) 0.0438(6) Uani 1 1 d . . . . .
C7 C 0.5035(3) 0.2057(3) 0.54527(16) 0.0494(6) Uani 1 1 d . . . . .
H7A H 0.5800 0.2963 0.5609 0.059 Uiso 1 1 calc R . . . .
H7B H 0.5469 0.1523 0.5874 0.059 Uiso 1 1 calc R . . . .
C20 C 1.0245(4) 0.3139(2) 0.09061(19) 0.0575(7) Uani 1 1 d . U . . .
H20 H 1.0528 0.3349 0.0311 0.069 Uiso 1 1 calc R . . . .
C23 C 1.1518(3) 0.6587(2) 0.22882(18) 0.0495(6) Uani 1 1 d . . . . .
H23A H 1.2042 0.7500 0.2496 0.074 Uiso 1 1 calc GR . . . .
H23B H 1.1524 0.6479 0.1625 0.074 Uiso 1 1 calc GR . . . .
H23C H 1.2175 0.6121 0.2623 0.074 Uiso 1 1 calc GR . . . .
C5 C 0.2372(4) 0.1034(2) 0.6217(2) 0.0608(7) Uani 1 1 d . . . . .
H5 H 0.2937 0.0542 0.6549 0.073 Uiso 1 1 calc R . . . .
C1 C 0.2323(4) 0.2604(3) 0.51080(18) 0.0568(7) Uani 1 1 d . . . . .
H1A H 0.2870 0.3180 0.4684 0.068 Uiso 1 1 calc R . . . .
C11 C 0.2934(4) -0.0172(2) 0.09471(19) 0.0632(8) Uani 1 1 d . . . . .
H11A H 0.1848 -0.0405 0.1203 0.076 Uiso 1 1 calc R . . . .
H11B H 0.3291 -0.0923 0.0950 0.076 Uiso 1 1 calc R . . . .
C19 C 1.1275(4) 0.2674(3) 0.1521(2) 0.0639(7) Uani 1 1 d . U . . .
H19 H 1.2282 0.2599 0.1353 0.077 Uiso 1 1 calc R . . . .
C18 C 1.0819(4) 0.2322(3) 0.2380(2) 0.0598(7) Uani 1 1 d . . . . .
H18 H 1.1499 0.1987 0.2793 0.072 Uiso 1 1 calc R . . . .
C12 C 0.2686(5) 0.0234(3) -0.0030(2) 0.0785(10) Uani 1 1 d . . . . .
H12A H 0.1826 -0.0486 -0.0427 0.118 Uiso 1 1 calc GR . . . .
H12B H 0.3779 0.0491 -0.0266 0.118 Uiso 1 1 calc GR . . . .
H12C H 0.2293 0.0957 -0.0025 0.118 Uiso 1 1 calc GR . . . .
C2 C 0.0674(5) 0.2475(4) 0.5233(2) 0.0772(9) Uani 1 1 d . . . . .
H2 H 0.0113 0.2972 0.4904 0.093 Uiso 1 1 calc R . . . .
C4 C 0.0660(5) 0.0904(3) 0.6341(3) 0.0846(11) Uani 1 1 d . . . . .
H4 H 0.0091 0.0333 0.6762 0.101 Uiso 1 1 calc R . . . .
C25 C 0.5621(4) 0.6667(3) 0.1678(2) 0.0793(10) Uani 1 1 d . . . . .
H25A H 0.4440 0.6052 0.1630 0.119 Uiso 1 1 calc GR . . . .
H25B H 0.5897 0.6855 0.1058 0.119 Uiso 1 1 calc GR . . . .
H25C H 0.5731 0.7460 0.2020 0.119 Uiso 1 1 calc GR . . . .
C3 C -0.0158(5) 0.1623(4) 0.5837(3) 0.0838(11) Uani 1 1 d . . . . .
H3 H -0.1295 0.1527 0.5909 0.101 Uiso 1 1 calc R . . . .


_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 C21 1.736(3) . ?
O2 C10 1.342(3) . ?
O2 C11 1.453(3) . ?
O3 C22 1.206(2) . ?
O1 C10 1.227(3) . ?
O4 C24 1.208(3) . ?
N2 C22 1.381(3) . ?
N2 C24 1.382(3) . ?
N2 C23 1.470(3) . ?
O5 C26 1.209(3) . ?
N3 C26 1.379(3) . ?
N3 C24 1.392(3) . ?
N3 C25 1.468(3) . ?
N1 H1 0.8600 . ?
N1 C8 1.342(3) . ?
N1 C7 1.454(3) . ?
C22 C14 1.513(3) . ?
C13 H13 0.9800 . ?
C13 C16 1.524(3) . ?
C13 C14 1.614(3) . ?
C13 C9 1.505(3) . ?
C16 C17 1.389(3) . ?
C16 C21 1.387(3) . ?
C14 C26 1.508(3) . ?
C14 C15 1.538(3) . ?
C9 C8 1.364(3) . ?
C9 C10 1.434(3) . ?
C8 C15 1.493(3) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C6 C7 1.509(3) . ?
C6 C5 1.377(3) . ?
C6 C1 1.381(3) . ?
C17 H17 0.9300 . ?
C17 C18 1.380(4) . ?
C21 C20 1.394(4) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C20 H20 0.9300 . ?
C20 C19 1.371(4) . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C5 H5 0.9300 . ?
C5 C4 1.409(4) . ?
C1 H1A 0.9300 . ?
C1 C2 1.358(4) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C12 1.490(4) . ?
C19 H19 0.9300 . ?
C19 C18 1.366(4) . ?
C18 H18 0.9300 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C2 H2 0.9300 . ?
C2 C3 1.358(5) . ?
C4 H4 0.9300 . ?
C4 C3 1.366(5) . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
C3 H3 0.9300 . ?

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
C10 O2 C11 117.82(18) . . ?
C22 N2 C23 118.49(18) . . ?
C24 N2 C22 124.36(18) . . ?
C24 N2 C23 116.94(18) . . ?
C26 N3 C24 124.57(18) . . ?
C26 N3 C25 118.4(2) . . ?
C24 N3 C25 117.0(2) . . ?
C8 N1 H1 116.7 . . ?
C8 N1 C7 126.6(2) . . ?
C7 N1 H1 116.7 . . ?
O3 C22 N2 121.54(19) . . ?
O3 C22 C14 123.48(18) . . ?
N2 C22 C14 114.79(17) . . ?
C16 C13 H13 109.0 . . ?
C16 C13 C14 113.74(16) . . ?
C14 C13 H13 109.0 . . ?
C9 C13 H13 109.0 . . ?
C9 C13 C16 114.25(17) . . ?
C9 C13 C14 101.66(15) . . ?
C17 C16 C13 120.89(19) . . ?
C21 C16 C13 123.0(2) . . ?
C21 C16 C17 116.1(2) . . ?
C22 C14 C13 109.66(16) . . ?
C22 C14 C15 112.46(17) . . ?
C26 C14 C22 112.19(17) . . ?
C26 C14 C13 105.13(16) . . ?
C26 C14 C15 111.12(18) . . ?
C15 C14 C13 105.82(15) . . ?
C8 C9 C13 113.18(18) . . ?
C8 C9 C10 123.62(19) . . ?
C10 C9 C13 122.99(18) . . ?
N1 C8 C9 125.9(2) . . ?
N1 C8 C15 122.23(19) . . ?
C9 C8 C15 111.85(18) . . ?
O5 C26 N3 121.3(2) . . ?
O5 C26 C14 122.9(2) . . ?
N3 C26 C14 115.52(19) . . ?
O4 C24 N2 121.6(2) . . ?
O4 C24 N3 121.4(2) . . ?
N2 C24 N3 116.94(19) . . ?
O2 C10 C9 112.29(18) . . ?
O1 C10 O2 122.7(2) . . ?
O1 C10 C9 124.9(2) . . ?
C14 C15 H15A 110.7 . . ?
C14 C15 H15B 110.7 . . ?
C8 C15 C14 105.24(16) . . ?
C8 C15 H15A 110.7 . . ?
C8 C15 H15B 110.7 . . ?
H15A C15 H15B 108.8 . . ?
C5 C6 C7 120.6(2) . . ?
C5 C6 C1 119.0(3) . . ?
C1 C6 C7 120.4(2) . . ?
C16 C17 H17 118.7 . . ?
C18 C17 C16 122.6(2) . . ?
C18 C17 H17 118.7 . . ?
C16 C21 Cl1 120.63(19) . . ?
C16 C21 C20 121.8(2) . . ?
C20 C21 Cl1 117.59(18) . . ?
N1 C7 C6 111.7(2) . . ?
N1 C7 H7A 109.3 . . ?
N1 C7 H7B 109.3 . . ?
C6 C7 H7A 109.3 . . ?
C6 C7 H7B 109.3 . . ?
H7A C7 H7B 107.9 . . ?
C21 C20 H20 120.1 . . ?
C19 C20 C21 119.8(2) . . ?
C19 C20 H20 120.1 . . ?
N2 C23 H23A 109.5 . . ?
N2 C23 H23B 109.5 . . ?
N2 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C6 C5 H5 120.3 . . ?
C6 C5 C4 119.5(3) . . ?
C4 C5 H5 120.3 . . ?
C6 C1 H1A 119.4 . . ?
C2 C1 C6 121.2(3) . . ?
C2 C1 H1A 119.4 . . ?
O2 C11 H11A 110.4 . . ?
O2 C11 H11B 110.4 . . ?
O2 C11 C12 106.8(2) . . ?
H11A C11 H11B 108.6 . . ?
C12 C11 H11A 110.4 . . ?
C12 C11 H11B 110.4 . . ?
C20 C19 H19 120.1 . . ?
C18 C19 C20 119.9(3) . . ?
C18 C19 H19 120.1 . . ?
C17 C18 H18 120.1 . . ?
C19 C18 C17 119.7(3) . . ?
C19 C18 H18 120.1 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C1 C2 H2 119.9 . . ?
C3 C2 C1 120.3(3) . . ?
C3 C2 H2 119.9 . . ?
C5 C4 H4 120.3 . . ?
C3 C4 C5 119.4(3) . . ?
C3 C4 H4 120.3 . . ?
N3 C25 H25A 109.5 . . ?
N3 C25 H25B 109.5 . . ?
N3 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C2 C3 C4 120.7(3) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 H3 119.7 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O1 0.86 2.20 2.805(3) 127.1 .
C15 H15A O3 0.97 2.61 3.376(3) 136.4 2_766
C20 H20 O4 0.93 2.60 3.447(3) 152.1 2_765
C23 H23A O1 0.96 2.58 3.533(3) 172.4 1_665

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 C21 C20 C19 179.5(2) . . . . ?
O3 C22 C14 C13 -96.8(2) . . . . ?
O3 C22 C14 C26 146.76(19) . . . . ?
O3 C22 C14 C15 20.6(3) . . . . ?
N2 C22 C14 C13 78.2(2) . . . . ?
N2 C22 C14 C26 -38.2(2) . . . . ?
N2 C22 C14 C15 -164.36(17) . . . . ?
N1 C8 C15 C14 -173.7(2) . . . . ?
C22 N2 C24 O4 177.7(2) . . . . ?
C22 N2 C24 N3 -0.4(3) . . . . ?
C22 C14 C26 O5 -151.3(2) . . . . ?
C22 C14 C26 N3 35.0(2) . . . . ?
C22 C14 C15 C8 -132.56(18) . . . . ?
C13 C16 C17 C18 -174.5(2) . . . . ?
C13 C16 C21 Cl1 -4.7(3) . . . . ?
C13 C16 C21 C20 175.3(2) . . . . ?
C13 C14 C26 O5 89.6(2) . . . . ?
C13 C14 C26 N3 -84.2(2) . . . . ?
C13 C14 C15 C8 -12.9(2) . . . . ?
C13 C9 C8 N1 -176.0(2) . . . . ?
C13 C9 C8 C15 4.3(3) . . . . ?
C13 C9 C10 O2 -6.8(3) . . . . ?
C13 C9 C10 O1 175.5(2) . . . . ?
C16 C13 C14 C22 13.0(2) . . . . ?
C16 C13 C14 C26 133.75(18) . . . . ?
C16 C13 C14 C15 -108.57(19) . . . . ?
C16 C13 C9 C8 111.0(2) . . . . ?
C16 C13 C9 C10 -74.1(3) . . . . ?
C16 C17 C18 C19 -1.2(4) . . . . ?
C16 C21 C20 C19 -0.6(4) . . . . ?
C14 C13 C16 C17 72.1(2) . . . . ?
C14 C13 C16 C21 -105.1(2) . . . . ?
C14 C13 C9 C8 -11.9(2) . . . . ?
C14 C13 C9 C10 162.99(19) . . . . ?
C9 C13 C16 C17 -44.0(3) . . . . ?
C9 C13 C16 C21 138.8(2) . . . . ?
C9 C13 C14 C22 136.25(17) . . . . ?
C9 C13 C14 C26 -102.95(18) . . . . ?
C9 C13 C14 C15 14.7(2) . . . . ?
C9 C8 C15 C14 6.0(2) . . . . ?
C8 N1 C7 C6 111.6(3) . . . . ?
C8 C9 C10 O2 167.6(2) . . . . ?
C8 C9 C10 O1 -10.1(4) . . . . ?
C26 N3 C24 O4 178.4(2) . . . . ?
C26 N3 C24 N2 -3.5(3) . . . . ?
C26 C14 C15 C8 100.7(2) . . . . ?
C24 N2 C22 O3 -162.74(19) . . . . ?
C24 N2 C22 C14 22.1(3) . . . . ?
C24 N3 C26 O5 171.0(2) . . . . ?
C24 N3 C26 C14 -15.1(3) . . . . ?
C10 O2 C11 C12 164.4(2) . . . . ?
C10 C9 C8 N1 9.1(4) . . . . ?
C10 C9 C8 C15 -170.6(2) . . . . ?
C15 C14 C26 O5 -24.4(3) . . . . ?
C15 C14 C26 N3 161.81(18) . . . . ?
C6 C5 C4 C3 0.8(5) . . . . ?
C6 C1 C2 C3 -1.1(4) . . . . ?
C17 C16 C21 Cl1 177.97(16) . . . . ?
C17 C16 C21 C20 -2.0(3) . . . . ?
C21 C16 C17 C18 2.9(3) . . . . ?
C21 C20 C19 C18 2.4(4) . . . . ?
C7 N1 C8 C9 -170.2(2) . . . . ?
C7 N1 C8 C15 9.5(4) . . . . ?
C7 C6 C5 C4 179.9(2) . . . . ?
C7 C6 C1 C2 -179.8(2) . . . . ?
C20 C19 C18 C17 -1.5(4) . . . . ?
C23 N2 C22 O3 11.8(3) . . . . ?
C23 N2 C22 C14 -163.27(18) . . . . ?
C23 N2 C24 O4 3.0(3) . . . . ?
C23 N2 C24 N3 -175.02(19) . . . . ?
C5 C6 C7 N1 117.6(3) . . . . ?
C5 C6 C1 C2 0.8(4) . . . . ?
C5 C4 C3 C2 -1.1(5) . . . . ?
C1 C6 C7 N1 -61.8(3) . . . . ?
C1 C6 C5 C4 -0.6(4) . . . . ?
C1 C2 C3 C4 1.3(5) . . . . ?
C11 O2 C10 O1 5.5(3) . . . . ?
C11 O2 C10 C9 -172.3(2) . . . . ?
C25 N3 C26 O5 -7.5(3) . . . . ?
C25 N3 C26 C14 166.4(2) . . . . ?
C25 N3 C24 O4 -3.0(3) . . . . ?
C25 N3 C24 N2 175.0(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_1_a
_database_code_depnum_ccdc_archive 'CCDC 2305868'
loop_
_audit_author_name
_audit_author_address
'Hui Xu'
;Anuhui Polytechnic University
China
;
_audit_update_record             
;
2023-11-06 deposited with the CCDC.	2024-03-12 downloaded from the CCDC.
;
_audit_creation_method           
;FinalCif V117 by Daniel Kratzert, Freiburg 2023,
https://dkratzert.de/finalcif.html
;
_audit_creation_date             2023-08-15
_diffrn_source_power             0.07
_exptl_crystal_colour_primary    colourless
_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 Ternary CH refined with riding coordinates:
 C2(H2)
2.b Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B), C13(H13A,H13B)
2.c Aromatic/amide H refined with riding coordinates:
 C23(H23), C4(H4), C19(H19), C10(H10), C5(H5), C20(H20), C21(H21), C22(H22)
2.d Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C25(H25A,H25B,H25C), C27(H27A,H27B,H27C), C7(H7A,H7B,
 H7C), C8(H8A,H8B,H8C)
;
_olex2_submission_special_instructions 'No special instructions were received'
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_sum            'C28.01 H30.01 Br N3 O5'
_chemical_formula_moiety         'C28 H30 Br N3 O5'
_chemical_formula_weight         568.65
_chemical_melting_point          ?
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   11.0881(8)
_cell_length_b                   11.9277(9)
_cell_length_c                   12.1514(9)
_cell_angle_alpha                115.124(2)
_cell_angle_beta                 105.133(3)
_cell_angle_gamma                100.196(3)
_cell_volume                     1326.22(17)
_cell_formula_units_Z            2
_cell_measurement_temperature    298.0
_cell_measurement_reflns_used    5919
_cell_measurement_theta_min      2.24
_cell_measurement_theta_max      24.80
_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_recrystallization_method ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.424
_exptl_crystal_F_000             588
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    1.593
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  0.5574
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction:
Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D., J. Appl. Cryst. 48
(2015) 3-10
;
_exptl_absorpt_special_details   ?
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_special_details           ?
_diffrn_ambient_temperature      298.0
_diffrn_ambient_environment      ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  ?
_diffrn_measurement_ambient_temperature_device_make ?
_diffrn_radiation_probe          ?
_diffrn_source                   ?
_diffrn_source_type              ?
_diffrn_source_voltage           50.0
_diffrn_source_current           1.4
_diffrn_detector                 ?
_diffrn_detector_type            ?
_diffrn_detector_area_resol_mean ?
_diffrn_measurement_device       ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_measurement_specimen_support ?
_diffrn_reflns_number            37795
_diffrn_reflns_av_unetI/netI     0.0570
_diffrn_reflns_av_R_equivalents  0.1052
_diffrn_reflns_theta_min         2.240
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_standards_number         0
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4666
_reflns_number_gt                3509
_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 BIS V6.2.16/2021-10-22 && APEX4 2021.10-0'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_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)+(0.0526P)²+0.3504P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_reflns         4666
_refine_ls_number_parameters     347
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0609
_refine_ls_R_factor_gt           0.0415
_refine_ls_wR_factor_ref         0.1144
_refine_ls_wR_factor_gt          0.1067
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_restrained_S_all      1.051
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.292
_refine_diff_density_min         -0.453
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .

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'
Br Br -0.2901 2.4595 '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'

_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_
_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
Br1 Br 0.45961(4) 0.35532(4) 0.81585(4) 0.08224(19) Uani 1 1 d . . . A 1
O4 O 0.40309(16) 0.30433(18) 0.34545(17) 0.0456(4) Uani 1 1 d . . . . .
O3 O 0.6600(2) 0.14840(18) 0.63231(19) 0.0530(5) Uani 1 1 d . . . . .
O2 O 0.95541(19) 0.5018(2) 0.6702(2) 0.0562(5) Uani 1 1 d . . . . .
O5 O 0.34464(18) 0.3829(2) 0.5188(2) 0.0611(6) Uani 1 1 d . . . . .
N1 N 0.73766(19) 0.41166(19) 0.72258(19) 0.0350(5) Uani 1 1 d . . . . .
N2 N 0.8023(2) 0.1133(2) 0.5275(2) 0.0435(5) Uani 1 1 d . . . . .
N3 N 0.9553(2) 0.2962(2) 0.5508(2) 0.0457(6) Uani 1 1 d . . . . .
O1 O 0.9513(2) 0.0885(2) 0.4304(2) 0.0715(7) Uani 1 1 d . . . . .
C28 C 0.9016(2) 0.3853(3) 0.6181(2) 0.0403(6) Uani 1 1 d . . . . .
C1 C 0.7651(2) 0.3265(2) 0.6108(2) 0.0341(5) Uani 1 1 d . . . . .
C11 C 0.5558(2) 0.3560(2) 0.5457(2) 0.0353(5) Uani 1 1 d . . . . .
C3 C 0.6254(2) 0.2009(2) 0.3616(2) 0.0371(6) Uani 1 1 d . . . . .
C12 C 0.4256(2) 0.3506(2) 0.4735(3) 0.0397(6) Uani 1 1 d . . . . .
C18 C 0.8601(2) 0.5649(3) 0.9630(2) 0.0398(6) Uani 1 1 d . . . . .
C15 C 0.6093(2) 0.4110(2) 0.6777(2) 0.0346(5) Uani 1 1 d . . . A 1
C17 C 0.8051(3) 0.4255(3) 0.8515(2) 0.0402(6) Uani 1 1 d . . . . .
C24 C 0.7377(2) 0.1893(2) 0.5939(2) 0.0387(6) Uani 1 1 d . . . . .
C2 C 0.6602(2) 0.3232(2) 0.4901(2) 0.0354(5) Uani 1 1 d . . . . .
H2 H 0.701118 0.397758 0.482084 0.042 Uiso 1 1 calc R U . . .
C16 C 0.5492(3) 0.4763(3) 0.7729(3) 0.0460(7) Uani 1 1 d . . . A 1
H16A H 0.486555 0.510147 0.735625 0.055 Uiso 1 1 calc R U . A 1
H16B H 0.617867 0.549803 0.852369 0.055 Uiso 1 1 calc R U . A 1
C13 C 0.2695(3) 0.2764(3) 0.2607(3) 0.0492(7) Uani 1 1 d . . . . .
H13A H 0.270841 0.276602 0.181257 0.059 Uiso 1 1 calc R U . . .
H13B H 0.234960 0.344343 0.304941 0.059 Uiso 1 1 calc R U . . .
C23 C 0.9458(3) 0.6622(3) 0.9608(3) 0.0516(7) Uani 1 1 d . . . . .
H23 H 0.969899 0.641918 0.888638 0.062 Uiso 1 1 calc R U . . .
C4 C 0.5289(3) 0.0848(3) 0.3201(3) 0.0463(6) Uani 1 1 d . . . . .
H4 H 0.475885 0.082511 0.367707 0.056 Uiso 1 1 calc R U . . .
C26 C 0.9043(3) 0.1615(3) 0.4967(3) 0.0480(7) Uani 1 1 d . . . . .
C19 C 0.8268(3) 0.5974(3) 1.0725(3) 0.0546(7) Uani 1 1 d . . . . .
H19 H 0.770458 0.533093 1.077031 0.066 Uiso 1 1 calc R U . . .
C10 C 0.7004(3) 0.2005(3) 0.2863(3) 0.0511(7) Uani 1 1 d . . . . .
H10 H 0.763097 0.278673 0.311243 0.061 Uiso 1 1 calc R U . . .
C14 C 0.1813(3) 0.1461(3) 0.2255(3) 0.0653(9) Uani 1 1 d . . . . .
H14A H 0.098268 0.122718 0.157800 0.098 Uiso 1 1 calc R U . . .
H14B H 0.166483 0.151058 0.301603 0.098 Uiso 1 1 calc R U . . .
H14C H 0.222565 0.080992 0.194657 0.098 Uiso 1 1 calc R U . . .
C6 C 0.5902(4) -0.0283(3) 0.1349(3) 0.0617(9) Uani 1 1 d . . . . .
C9 C 0.6852(3) 0.0876(4) 0.1751(3) 0.0589(8) Uani 1 1 d . . . . .
C5 C 0.5113(3) -0.0279(3) 0.2079(3) 0.0571(8) Uani 1 1 d . . . . .
H5 H 0.445517 -0.105061 0.180481 0.069 Uiso 1 1 calc R U . . .
C20 C 0.8782(3) 0.7270(4) 1.1763(3) 0.0645(9) Uani 1 1 d . . . . .
H20 H 0.854836 0.748725 1.249056 0.077 Uiso 1 1 calc R U . . .
C21 C 0.9614(3) 0.8209(3) 1.1713(3) 0.0657(9) Uani 1 1 d . . . . .
H21 H 0.994977 0.906759 1.240450 0.079 Uiso 1 1 calc R U . . .
C25 C 0.7561(3) -0.0282(3) 0.4810(3) 0.0669(9) Uani 1 1 d . . . . .
H25A H 0.800061 -0.044648 0.549066 0.100 Uiso 1 1 calc R U . . .
H25B H 0.775772 -0.074440 0.404934 0.100 Uiso 1 1 calc R U . . .
H25C H 0.662274 -0.057793 0.458698 0.100 Uiso 1 1 calc R U . . .
C22 C 0.9962(4) 0.7891(3) 1.0639(3) 0.0673(9) Uani 1 1 d . . . . .
H22 H 1.054053 0.853516 1.060860 0.081 Uiso 1 1 calc R U . . .
C27 C 1.0761(3) 0.3465(4) 0.5334(4) 0.0777(11) Uani 1 1 d . . . . .
H27A H 1.052212 0.351280 0.454087 0.117 Uiso 1 1 calc R U . . .
H27B H 1.127185 0.288601 0.528023 0.117 Uiso 1 1 calc R U . . .
H27C H 1.127534 0.432329 0.606812 0.117 Uiso 1 1 calc R U . . .
C7 C 0.5720(5) -0.1550(4) 0.0164(3) 0.0943(14) Uani 1 1 d . . . . .
H7A H 0.568164 -0.140336 -0.055996 0.142 Uiso 1 1 calc R U . . .
H7B H 0.491241 -0.220115 -0.006621 0.142 Uiso 1 1 calc R U . . .
H7C H 0.645217 -0.185085 0.036864 0.142 Uiso 1 1 calc R U . . .
C8 C 0.7755(4) 0.0955(5) 0.1022(4) 0.1027(15) Uani 1 1 d . . . . .
H8A H 0.823987 0.185680 0.135661 0.154 Uiso 1 1 calc R U . . .
H8B H 0.723444 0.055998 0.010322 0.154 Uiso 1 1 calc R U . . .
H8C H 0.836338 0.049668 0.114296 0.154 Uiso 1 1 calc R U . . .
H17A H 0.751(2) 0.373(2) 0.867(2) 0.030(6) Uiso 1 1 d . . . . .
H17B H 0.875(3) 0.387(3) 0.843(3) 0.045(7) Uiso 1 1 d . . . . .


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
Br1 C16 1.936(3) . ?
O4 C12 1.344(3) . ?
O4 C13 1.450(3) . ?
O3 C24 1.206(3) . ?
O2 C28 1.204(3) . ?
O5 C12 1.207(3) . ?
N1 C1 1.457(3) . ?
N1 C15 1.382(3) . ?
N1 C17 1.472(3) . ?
N2 C24 1.377(3) . ?
N2 C26 1.386(4) . ?
N2 C25 1.471(4) . ?
N3 C28 1.376(3) . ?
N3 C26 1.386(4) . ?
N3 C27 1.472(4) . ?
O1 C26 1.210(3) . ?
C28 C1 1.514(3) . ?
C1 C24 1.522(4) . ?
C1 C2 1.597(3) . ?
C11 C12 1.454(3) . ?
C11 C15 1.352(3) . ?
C11 C2 1.515(3) . ?
C3 C2 1.506(3) . ?
C3 C4 1.386(4) . ?
C3 C10 1.386(4) . ?
C18 C17 1.506(4) . ?
C18 C23 1.378(4) . ?
C18 C19 1.388(4) . ?
C15 C16 1.486(3) . ?
C17 H17A 0.90(3) . ?
C17 H17B 0.98(3) . ?
C2 H2 0.9800 . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C14 1.494(4) . ?
C23 H23 0.9300 . ?
C23 C22 1.377(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.384(4) . ?
C19 H19 0.9300 . ?
C19 C20 1.401(4) . ?
C10 H10 0.9300 . ?
C10 C9 1.387(4) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C6 C9 1.378(5) . ?
C6 C5 1.399(5) . ?
C6 C7 1.514(4) . ?
C9 C8 1.517(5) . ?
C5 H5 0.9300 . ?
C20 H20 0.9300 . ?
C20 C21 1.352(5) . ?
C21 H21 0.9300 . ?
C21 C22 1.376(5) . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
C22 H22 0.9300 . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 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
C12 O4 C13 116.4(2) . . ?
C1 N1 C17 118.73(19) . . ?
C15 N1 C1 108.58(18) . . ?
C15 N1 C17 124.3(2) . . ?
C24 N2 C26 123.8(2) . . ?
C24 N2 C25 118.1(2) . . ?
C26 N2 C25 118.1(2) . . ?
C28 N3 C26 125.2(2) . . ?
C28 N3 C27 118.1(3) . . ?
C26 N3 C27 116.8(2) . . ?
O2 C28 N3 121.9(2) . . ?
O2 C28 C1 122.6(2) . . ?
N3 C28 C1 115.2(2) . . ?
N1 C1 C28 112.22(19) . . ?
N1 C1 C24 110.0(2) . . ?
N1 C1 C2 102.91(18) . . ?
C28 C1 C24 114.0(2) . . ?
C28 C1 C2 107.3(2) . . ?
C24 C1 C2 109.74(19) . . ?
C12 C11 C2 126.0(2) . . ?
C15 C11 C12 124.1(2) . . ?
C15 C11 C2 109.1(2) . . ?
C4 C3 C2 122.8(2) . . ?
C4 C3 C10 118.1(2) . . ?
C10 C3 C2 118.8(2) . . ?
O4 C12 C11 111.8(2) . . ?
O5 C12 O4 122.0(2) . . ?
O5 C12 C11 126.2(3) . . ?
C23 C18 C17 121.6(2) . . ?
C23 C18 C19 118.4(3) . . ?
C19 C18 C17 120.0(3) . . ?
N1 C15 C16 120.0(2) . . ?
C11 C15 N1 112.7(2) . . ?
C11 C15 C16 127.2(2) . . ?
N1 C17 C18 114.0(2) . . ?
N1 C17 H17A 110.0(15) . . ?
N1 C17 H17B 105.7(16) . . ?
C18 C17 H17A 111.6(15) . . ?
C18 C17 H17B 111.2(16) . . ?
H17A C17 H17B 104(2) . . ?
O3 C24 N2 122.2(2) . . ?
O3 C24 C1 121.6(2) . . ?
N2 C24 C1 116.2(2) . . ?
C1 C2 H2 107.2 . . ?
C11 C2 C1 100.24(18) . . ?
C11 C2 H2 107.2 . . ?
C3 C2 C1 112.98(19) . . ?
C3 C2 C11 121.1(2) . . ?
C3 C2 H2 107.2 . . ?
Br1 C16 H16A 109.4 . . ?
Br1 C16 H16B 109.4 . . ?
C15 C16 Br1 111.09(18) . . ?
C15 C16 H16A 109.4 . . ?
C15 C16 H16B 109.4 . . ?
H16A C16 H16B 108.0 . . ?
O4 C13 H13A 109.5 . . ?
O4 C13 H13B 109.5 . . ?
O4 C13 C14 110.9(2) . . ?
H13A C13 H13B 108.0 . . ?
C14 C13 H13A 109.5 . . ?
C14 C13 H13B 109.5 . . ?
C18 C23 H23 119.5 . . ?
C22 C23 C18 121.0(3) . . ?
C22 C23 H23 119.5 . . ?
C3 C4 H4 120.0 . . ?
C5 C4 C3 120.0(3) . . ?
C5 C4 H4 120.0 . . ?
N3 C26 N2 117.7(2) . . ?
O1 C26 N2 120.8(3) . . ?
O1 C26 N3 121.3(3) . . ?
C18 C19 H19 120.0 . . ?
C18 C19 C20 119.9(3) . . ?
C20 C19 H19 120.0 . . ?
C3 C10 H10 118.9 . . ?
C3 C10 C9 122.3(3) . . ?
C9 C10 H10 118.9 . . ?
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 . . ?
C9 C6 C5 118.5(3) . . ?
C9 C6 C7 121.7(3) . . ?
C5 C6 C7 119.8(4) . . ?
C10 C9 C8 118.5(3) . . ?
C6 C9 C10 119.5(3) . . ?
C6 C9 C8 121.9(3) . . ?
C4 C5 C6 121.5(3) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 H5 119.3 . . ?
C19 C20 H20 119.8 . . ?
C21 C20 C19 120.5(3) . . ?
C21 C20 H20 119.8 . . ?
C20 C21 H21 120.0 . . ?
C20 C21 C22 119.9(3) . . ?
C22 C21 H21 120.0 . . ?
N2 C25 H25A 109.5 . . ?
N2 C25 H25B 109.5 . . ?
N2 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C23 C22 H22 119.9 . . ?
C21 C22 C23 120.2(3) . . ?
C21 C22 H22 119.9 . . ?
N3 C27 H27A 109.5 . . ?
N3 C27 H27B 109.5 . . ?
N3 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C9 C8 H8A 109.5 . . ?
C9 C8 H8B 109.5 . . ?
C9 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 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
O2 C28 C1 N1 -30.4(3) . . . . ?
O2 C28 C1 C24 -156.4(3) . . . . ?
O2 C28 C1 C2 81.9(3) . . . . ?
N1 C1 C24 O3 25.8(3) . . . . ?
N1 C1 C24 N2 -157.0(2) . . . . ?
N1 C1 C2 C11 -24.2(2) . . . . ?
N1 C1 C2 C3 -154.4(2) . . . . ?
N1 C15 C16 Br1 -90.4(2) . . . . ?
N3 C28 C1 N1 155.2(2) . . . . ?
N3 C28 C1 C24 29.2(3) . . . . ?
N3 C28 C1 C2 -92.5(3) . . . . ?
C28 N3 C26 N2 -9.3(4) . . . . ?
C28 N3 C26 O1 174.5(3) . . . . ?
C28 C1 C24 O3 152.9(2) . . . . ?
C28 C1 C24 N2 -29.9(3) . . . . ?
C28 C1 C2 C11 -142.7(2) . . . . ?
C28 C1 C2 C3 87.0(2) . . . . ?
C1 N1 C15 C11 -12.5(3) . . . . ?
C1 N1 C15 C16 172.2(2) . . . . ?
C1 N1 C17 C18 135.0(2) . . . . ?
C11 C15 C16 Br1 95.0(3) . . . . ?
C3 C4 C5 C6 0.7(4) . . . . ?
C3 C10 C9 C6 1.8(4) . . . . ?
C3 C10 C9 C8 -177.5(3) . . . . ?
C12 O4 C13 C14 -80.8(3) . . . . ?
C12 C11 C15 N1 -175.7(2) . . . . ?
C12 C11 C15 C16 -0.8(4) . . . . ?
C12 C11 C2 C1 -171.3(2) . . . . ?
C12 C11 C2 C3 -46.5(4) . . . . ?
C18 C23 C22 C21 -0.1(5) . . . . ?
C18 C19 C20 C21 -0.8(5) . . . . ?
C15 N1 C1 C28 138.1(2) . . . . ?
C15 N1 C1 C24 -93.8(2) . . . . ?
C15 N1 C1 C2 23.1(2) . . . . ?
C15 N1 C17 C18 -80.6(3) . . . . ?
C15 C11 C12 O4 172.8(2) . . . . ?
C15 C11 C12 O5 -7.0(4) . . . . ?
C15 C11 C2 C1 18.2(2) . . . . ?
C15 C11 C2 C3 143.1(2) . . . . ?
C17 N1 C1 C28 -72.4(3) . . . . ?
C17 N1 C1 C24 55.6(3) . . . . ?
C17 N1 C1 C2 172.5(2) . . . . ?
C17 N1 C15 C11 -159.9(2) . . . . ?
C17 N1 C15 C16 24.8(3) . . . . ?
C17 C18 C23 C22 -179.5(3) . . . . ?
C17 C18 C19 C20 179.9(3) . . . . ?
C24 N2 C26 N3 8.8(4) . . . . ?
C24 N2 C26 O1 -175.0(3) . . . . ?
C24 C1 C2 C11 92.9(2) . . . . ?
C24 C1 C2 C3 -37.3(3) . . . . ?
C2 C1 C24 O3 -86.8(3) . . . . ?
C2 C1 C24 N2 90.5(2) . . . . ?
C2 C11 C12 O4 3.8(3) . . . . ?
C2 C11 C12 O5 -176.0(3) . . . . ?
C2 C11 C15 N1 -5.0(3) . . . . ?
C2 C11 C15 C16 169.9(2) . . . . ?
C2 C3 C4 C5 -173.1(2) . . . . ?
C2 C3 C10 C9 172.0(2) . . . . ?
C13 O4 C12 O5 -9.1(4) . . . . ?
C13 O4 C12 C11 171.1(2) . . . . ?
C23 C18 C17 N1 -55.0(3) . . . . ?
C23 C18 C19 C20 1.2(4) . . . . ?
C4 C3 C2 C1 84.7(3) . . . . ?
C4 C3 C2 C11 -34.0(4) . . . . ?
C4 C3 C10 C9 -2.5(4) . . . . ?
C26 N2 C24 O3 -171.4(2) . . . . ?
C26 N2 C24 C1 11.4(3) . . . . ?
C26 N3 C28 O2 175.0(3) . . . . ?
C26 N3 C28 C1 -10.5(4) . . . . ?
C19 C18 C17 N1 126.3(3) . . . . ?
C19 C18 C23 C22 -0.7(4) . . . . ?
C19 C20 C21 C22 -0.1(5) . . . . ?
C10 C3 C2 C1 -89.5(3) . . . . ?
C10 C3 C2 C11 151.7(2) . . . . ?
C10 C3 C4 C5 1.2(4) . . . . ?
C9 C6 C5 C4 -1.5(4) . . . . ?
C5 C6 C9 C10 0.3(4) . . . . ?
C5 C6 C9 C8 179.5(3) . . . . ?
C20 C21 C22 C23 0.5(5) . . . . ?
C25 N2 C24 O3 11.6(4) . . . . ?
C25 N2 C24 C1 -165.6(2) . . . . ?
C25 N2 C26 N3 -174.3(2) . . . . ?
C25 N2 C26 O1 2.0(4) . . . . ?
C27 N3 C28 O2 -5.3(4) . . . . ?
C27 N3 C28 C1 169.1(2) . . . . ?
C27 N3 C26 N2 171.0(3) . . . . ?
C27 N3 C26 O1 -5.2(4) . . . . ?
C7 C6 C9 C10 -178.3(3) . . . . ?
C7 C6 C9 C8 1.0(5) . . . . ?
C7 C6 C5 C4 177.1(3) . . . . ?

