# Electronic Supplementary Material (ESI) for RSC Advances.
# 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 
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data_2_pl
_audit_block_doi                 10.5517/ccdc.csd.cc24462l
_database_code_depnum_ccdc_archive 'CCDC 1970238'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1007/s11030-020-10114-1 2021
loop_
_audit_author_name
_audit_author_address
'Alireza Abbasi'
;Tehran University
Iran
;
_audit_update_record             
;
2019-12-05 deposited with the CCDC.	2022-11-29 downloaded from the CCDC.
;
_audit_creation_date             2019-11-05
_audit_creation_method           
;
Olex2 1.3
(compiled 2019.09.11 svn.r3662 for OlexSys, GUI svn.r5938)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C27 H25 Cl N4 O4, H2 O'
_chemical_formula_sum            'C27 H27 Cl N4 O5'
_chemical_formula_weight         522.97
_chemical_absolute_configuration unk
_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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   9.7052(19)
_cell_length_b                   13.015(3)
_cell_length_c                   19.712(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2489.9(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    13987
_cell_measurement_temperature    293.15
_cell_measurement_theta_max      25.0
_cell_measurement_theta_min      2.1
_shelx_estimated_absorpt_T_max   0.971
_shelx_estimated_absorpt_T_min   0.952
_exptl_absorpt_coefficient_mu    0.200
_exptl_absorpt_correction_T_max  1.06285
_exptl_absorpt_correction_T_min  0.96275
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'R.H. Blessing, Acta Crystallogr., Sect A 1995, 51, 33-38'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.395
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       irregular
_exptl_crystal_F_000             1096
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0750
_diffrn_reflns_av_unetI/netI     0.0512
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            13987
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         2.066
_diffrn_ambient_temperature      293.15
_diffrn_detector                 'image-plate detector'
_diffrn_detector_area_resol_mean 0.81
_diffrn_detector_type            MAR345-dtb
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device       'one-circle diffractometer'
_diffrn_measurement_device_type  MAR345
_diffrn_measurement_method       'image-plate detector - phi oscillation'
_diffrn_radiation_monochromator  mirrors
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_target            Mo
_reflns_Friedel_coverage         0.755
_reflns_Friedel_fraction_full    0.986
_reflns_Friedel_fraction_max     0.986
_reflns_number_gt                4148
_reflns_number_total             4325
_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       'Automar software package (3.3a, 2015)'
_computing_data_collection       'MAR345 dtb Program (1.24-4, 2013)'
_computing_data_reduction        'Automar software package (3.3a, 2015)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 1999)'
_computing_publication_material  'PLATON (2018)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.322
_refine_diff_density_min         -0.229
_refine_diff_density_rms         0.049
_refine_ls_abs_structure_details 
;
 Flack x determined using 1574 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.05(6)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     360
_refine_ls_number_reflns         4325
_refine_ls_number_restraints     14
_refine_ls_R_factor_all          0.0524
_refine_ls_R_factor_gt           0.0490
_refine_ls_restrained_S_all      1.086
_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)+(0.0534P)²+1.2688P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1234
_refine_ls_wR_factor_ref         0.1247
_refine_special_details          ?
_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, All O(H,H) groups
2. Restrained distances
 H5B-N5
 0.87 with sigma of 0.02
 H1-O1
 0.82 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
C13 \\sim C22 \\sim C26: within 2A with sigma of 0.001 and sigma for terminal
atoms of 0.002 within 2A
4.a Free rotating group:
 O6(H6A,H6B)
4.b Rotating group:
 N3(H3A)
4.c Ternary CH refined with riding coordinates:
 C5(H5)
4.d Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C26(H26A,H26B)
4.e Aromatic/amide H refined with riding coordinates:
 C1(H1A), C4(H4), C14(H14), C16(H16), C18(H18), C19(H19), C23(H23), C24(H24)
4.f Idealised Me refined as rotating group:
 C25(H25A,H25B,H25C), C27(H27A,H27B,H27C)
;
_atom_sites_solution_hydrogens   mixed
_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
Cl1 Cl -1.51494(17) 0.23850(13) 1.61298(8) 0.0859(5) Uani 1 1 d . . . . .
O1 O -1.5784(3) 0.5728(2) 1.41532(14) 0.0463(7) Uani 1 1 d D . . . .
O2 O -1.3789(3) 0.3331(2) 1.35105(16) 0.0524(8) Uani 1 1 d . . . . .
O3 O -1.4545(3) 0.5940(3) 1.28998(14) 0.0530(8) Uani 1 1 d . . . . .
O4 O -1.0036(3) 0.7818(2) 1.45147(14) 0.0485(7) Uani 1 1 d . . . . .
N5 N -0.9197(4) 0.6705(3) 1.3484(2) 0.0482(9) Uani 1 1 d D . . . .
N1 N -1.0515(3) 0.5294(2) 1.31878(15) 0.0366(7) Uani 1 1 d . . . . .
C1 C -1.2436(4) 0.5698(3) 1.41744(17) 0.0335(8) Uani 1 1 d . . . . .
H1A H -1.299211 0.577507 1.455521 0.040 Uiso 1 1 calc R U . . .
N2 N -1.0601(4) 0.4485(3) 1.17964(18) 0.0456(8) Uani 1 1 d . . . . .
N3 N -1.2090(4) 0.7506(3) 1.4993(2) 0.0511(9) Uani 1 1 d . . . . .
H3A H -1.180762 0.798954 1.526630 0.061 Uiso 1 1 d R U . . .
C28 C -1.2703(4) 0.4905(3) 1.37397(17) 0.0322(7) Uani 1 1 d . . . . .
C3 C -1.2549(4) 0.5165(3) 1.24369(18) 0.0355(8) Uani 1 1 d . . . . .
C4 C -0.8228(4) 0.4515(3) 1.3287(2) 0.0467(10) Uani 1 1 d . . . . .
H4 H -0.815235 0.479166 1.372009 0.056 Uiso 1 1 calc R U . . .
C5 C -1.1889(3) 0.4806(3) 1.30946(17) 0.0328(7) Uani 1 1 d . . . . .
H5 H -1.171190 0.406976 1.303665 0.039 Uiso 1 1 calc R U . . .
C6 C -1.3847(4) 0.5693(3) 1.23993(19) 0.0414(9) Uani 1 1 d . . . . .
C7 C -1.4601(4) 0.4153(3) 1.44964(18) 0.0371(8) Uani 1 1 d . . . . .
C8 C -1.5592(4) 0.4924(3) 1.45883(19) 0.0407(8) Uani 1 1 d . . . . .
C9 C -1.3681(4) 0.4104(3) 1.38765(18) 0.0364(8) Uani 1 1 d . . . . .
C10 C -1.0339(4) 0.6151(3) 1.35687(18) 0.0365(8) Uani 1 1 d . . . . .
C11 C -0.9382(4) 0.4739(3) 1.29022(19) 0.0368(8) Uani 1 1 d . . . . .
C12 C -1.5364(5) 0.3341(4) 1.5528(2) 0.0511(10) Uani 1 1 d . . . . .
C13 C -1.2481(5) 0.5123(5) 1.1153(2) 0.0560(9) Uani 1 1 d . U . . .
H13A H -1.226062 0.454699 1.086007 0.067 Uiso 1 1 calc R U . . .
H13B H -1.203748 0.572675 1.096441 0.067 Uiso 1 1 calc R U . . .
C14 C -1.4509(4) 0.3368(3) 1.4961(2) 0.0445(9) Uani 1 1 d . . . . .
H14 H -1.386545 0.284805 1.489571 0.053 Uiso 1 1 calc R U . . .
C15 C -1.1351(4) 0.6409(3) 1.40715(18) 0.0347(8) Uani 1 1 d . . . . .
C16 C -0.7299(4) 0.3484(4) 1.2403(3) 0.0540(11) Uani 1 1 d . . . . .
H16 H -0.660521 0.306083 1.223550 0.065 Uiso 1 1 calc R U . . .
C17 C -0.9499(4) 0.4315(3) 1.22486(19) 0.0396(8) Uani 1 1 d . . . . .
C18 C -0.7189(5) 0.3896(4) 1.3047(3) 0.0545(11) Uani 1 1 d . . . . .
H18 H -0.642218 0.375535 1.331488 0.065 Uiso 1 1 calc R U . . .
C19 C -1.6347(5) 0.4096(4) 1.5616(2) 0.0537(11) Uani 1 1 d . . . . .
H19 H -1.692422 0.408096 1.599257 0.064 Uiso 1 1 calc R U . . .
C20 C -1.1116(4) 0.7272(3) 1.45295(19) 0.0386(8) Uani 1 1 d . . . . .
C21 C -1.1879(4) 0.4921(3) 1.18389(19) 0.0408(9) Uani 1 1 d . . . . .
C22 C -1.4015(5) 0.5287(4) 1.1138(2) 0.0561(8) Uani 1 1 d . U . . .
C23 C -1.6467(5) 0.4872(4) 1.5144(2) 0.0506(10) Uani 1 1 d . . . . .
H23 H -1.714687 0.536841 1.519862 0.061 Uiso 1 1 calc R U . . .
C24 C -0.8430(4) 0.3698(4) 1.2010(2) 0.0506(10) Uani 1 1 d . . . . .
H24 H -0.848420 0.342492 1.157495 0.061 Uiso 1 1 calc R U . . .
C25 C -1.4460(6) 0.5743(5) 1.0454(2) 0.0709(15) Uani 1 1 d . . . . .
H25A H -1.400146 0.638786 1.038390 0.106 Uiso 1 1 calc R U . . .
H25B H -1.543878 0.584847 1.045361 0.106 Uiso 1 1 calc R U . . .
H25C H -1.421702 0.527688 1.009555 0.106 Uiso 1 1 calc R U . . .
C26 C -1.4392(5) 0.6001(4) 1.1707(2) 0.0599(9) Uani 1 1 d . U . . .
H26A H -1.538848 0.604479 1.173249 0.072 Uiso 1 1 calc R U . . .
H26B H -1.404752 0.668115 1.159986 0.072 Uiso 1 1 calc R U . . .
C27 C -1.4759(7) 0.4266(5) 1.1236(3) 0.0885(19) Uani 1 1 d . . . . .
H27A H -1.451646 0.380653 1.087387 0.133 Uiso 1 1 calc R U . . .
H27B H -1.573605 0.437868 1.123334 0.133 Uiso 1 1 calc R U . . .
H27C H -1.449104 0.396900 1.166179 0.133 Uiso 1 1 calc R U . . .
O6 O -0.6994(5) 0.7093(5) 1.2627(3) 0.119(2) Uani 1 1 d G . . . .
H6A H -0.624305 0.677632 1.270208 0.179 Uiso 1 1 d G U . . .
H6B H -0.689879 0.734129 1.223092 0.179 Uiso 1 1 d G U . . .
H3B H -1.289(5) 0.726(4) 1.501(2) 0.041(12) Uiso 1 1 d . . . . .
H5A H -0.861(5) 0.659(4) 1.317(3) 0.050(13) Uiso 1 1 d . . . . .
H5B H -0.916(5) 0.728(3) 1.373(2) 0.049(12) Uiso 1 1 d D . . . .
H2 H -1.035(7) 0.443(5) 1.143(3) 0.082(19) Uiso 1 1 d . . . . .
H1 H -1.529(5) 0.572(4) 1.3795(18) 0.066(16) Uiso 1 1 d 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
Cl1 C12 1.732(4) . ?
O1 C8 1.366(5) . ?
O1 H1 0.85(3) . ?
O2 C9 1.242(5) . ?
O3 C6 1.239(5) . ?
O4 C20 1.267(5) . ?
N5 C10 1.333(5) . ?
N5 H5A 0.86(5) . ?
N5 H5B 0.89(3) . ?
N1 C5 1.489(5) . ?
N1 C10 1.355(5) . ?
N1 C11 1.431(5) . ?
C1 H1A 0.9300 . ?
C1 C28 1.366(5) . ?
C1 C15 1.416(5) . ?
N2 C17 1.410(5) . ?
N2 C21 1.366(5) . ?
N2 H2 0.77(6) . ?
N3 H3A 0.8720 . ?
N3 C20 1.350(5) . ?
N3 H3B 0.84(5) . ?
C28 C5 1.502(5) . ?
C28 C9 1.436(5) . ?
C3 C5 1.520(5) . ?
C3 C6 1.437(5) . ?
C3 C21 1.383(5) . ?
C4 H4 0.9300 . ?
C4 C11 1.384(6) . ?
C4 C18 1.375(6) . ?
C5 H5 0.9800 . ?
C6 C26 1.517(5) . ?
C7 C8 1.401(6) . ?
C7 C9 1.515(5) . ?
C7 C14 1.375(6) . ?
C8 C23 1.388(6) . ?
C10 C15 1.435(5) . ?
C11 C17 1.406(5) . ?
C12 C14 1.393(6) . ?
C12 C19 1.380(7) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C21 1.496(5) . ?
C13 C22 1.505(6) . ?
C14 H14 0.9300 . ?
C15 C20 1.459(5) . ?
C16 H16 0.9300 . ?
C16 C18 1.383(7) . ?
C16 C24 1.372(6) . ?
C17 C24 1.394(6) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C19 C23 1.378(7) . ?
C22 C25 1.536(6) . ?
C22 C26 1.502(6) . ?
C22 C27 1.525(8) . ?
C23 H23 0.9300 . ?
C24 H24 0.9300 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?
O6 H6A 0.8508 . ?
O6 H6B 0.8500 . ?

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
C8 O1 H1 116(4) . . ?
C10 N5 H5A 123(3) . . ?
C10 N5 H5B 115(3) . . ?
H5A N5 H5B 121(5) . . ?
C10 N1 C5 122.2(3) . . ?
C10 N1 C11 122.5(3) . . ?
C11 N1 C5 115.1(3) . . ?
C28 C1 H1A 118.5 . . ?
C28 C1 C15 123.0(3) . . ?
C15 C1 H1A 118.5 . . ?
C17 N2 H2 110(5) . . ?
C21 N2 C17 135.6(3) . . ?
C21 N2 H2 112(5) . . ?
H3A N3 H3B 122.8 . . ?
C20 N3 H3A 111.2 . . ?
C20 N3 H3B 126(3) . . ?
C1 C28 C5 119.7(3) . . ?
C1 C28 C9 123.8(3) . . ?
C9 C28 C5 116.4(3) . . ?
C6 C3 C5 124.1(3) . . ?
C21 C3 C5 117.3(3) . . ?
C21 C3 C6 118.5(3) . . ?
C11 C4 H4 119.0 . . ?
C18 C4 H4 119.0 . . ?
C18 C4 C11 122.0(4) . . ?
N1 C5 C28 109.3(3) . . ?
N1 C5 C3 110.6(3) . . ?
N1 C5 H5 106.0 . . ?
C28 C5 C3 118.3(3) . . ?
C28 C5 H5 106.0 . . ?
C3 C5 H5 106.0 . . ?
O3 C6 C3 124.2(3) . . ?
O3 C6 C26 117.2(3) . . ?
C3 C6 C26 118.6(3) . . ?
C8 C7 C9 122.6(3) . . ?
C14 C7 C8 119.4(4) . . ?
C14 C7 C9 117.9(3) . . ?
O1 C8 C7 124.1(3) . . ?
O1 C8 C23 116.7(4) . . ?
C23 C8 C7 119.1(4) . . ?
O2 C9 C28 122.3(3) . . ?
O2 C9 C7 116.9(3) . . ?
C28 C9 C7 120.7(3) . . ?
N5 C10 N1 118.8(3) . . ?
N5 C10 C15 121.9(3) . . ?
N1 C10 C15 119.3(3) . . ?
C4 C11 N1 120.9(3) . . ?
C4 C11 C17 119.0(3) . . ?
C17 C11 N1 119.8(3) . . ?
C14 C12 Cl1 119.7(4) . . ?
C19 C12 Cl1 120.5(3) . . ?
C19 C12 C14 119.7(4) . . ?
H13A C13 H13B 107.5 . . ?
C21 C13 H13A 108.4 . . ?
C21 C13 H13B 108.4 . . ?
C21 C13 C22 115.4(4) . . ?
C22 C13 H13A 108.4 . . ?
C22 C13 H13B 108.4 . . ?
C7 C14 C12 121.0(4) . . ?
C7 C14 H14 119.5 . . ?
C12 C14 H14 119.5 . . ?
C1 C15 C10 117.1(3) . . ?
C1 C15 C20 122.0(3) . . ?
C10 C15 C20 120.0(3) . . ?
C18 C16 H16 119.9 . . ?
C24 C16 H16 119.9 . . ?
C24 C16 C18 120.1(4) . . ?
C11 C17 N2 125.4(3) . . ?
C24 C17 N2 116.2(3) . . ?
C24 C17 C11 118.3(4) . . ?
C4 C18 C16 119.1(4) . . ?
C4 C18 H18 120.5 . . ?
C16 C18 H18 120.5 . . ?
C12 C19 H19 120.2 . . ?
C23 C19 C12 119.6(4) . . ?
C23 C19 H19 120.2 . . ?
O4 C20 N3 117.9(4) . . ?
O4 C20 C15 123.2(3) . . ?
N3 C20 C15 118.9(4) . . ?
N2 C21 C3 125.0(4) . . ?
N2 C21 C13 111.8(3) . . ?
C3 C21 C13 123.1(3) . . ?
C13 C22 C25 110.5(4) . . ?
C13 C22 C27 110.0(5) . . ?
C26 C22 C13 108.3(4) . . ?
C26 C22 C25 110.5(4) . . ?
C26 C22 C27 109.3(5) . . ?
C27 C22 C25 108.3(5) . . ?
C8 C23 H23 119.4 . . ?
C19 C23 C8 121.1(4) . . ?
C19 C23 H23 119.4 . . ?
C16 C24 C17 121.5(4) . . ?
C16 C24 H24 119.2 . . ?
C17 C24 H24 119.2 . . ?
C22 C25 H25A 109.5 . . ?
C22 C25 H25B 109.5 . . ?
C22 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C6 C26 H26A 108.5 . . ?
C6 C26 H26B 108.5 . . ?
C22 C26 C6 115.1(4) . . ?
C22 C26 H26A 108.5 . . ?
C22 C26 H26B 108.5 . . ?
H26A C26 H26B 107.5 . . ?
C22 C27 H27A 109.5 . . ?
C22 C27 H27B 109.5 . . ?
C22 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
H6A O6 H6B 104.5 . . ?

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 C12 C14 C7 -176.1(3) . . . . ?
Cl1 C12 C19 C23 177.6(4) . . . . ?
O1 C8 C23 C19 -179.3(4) . . . . ?
O3 C6 C26 C22 -149.6(4) . . . . ?
N5 C10 C15 C1 -172.4(4) . . . . ?
N5 C10 C15 C20 -2.9(6) . . . . ?
N1 C10 C15 C1 4.7(5) . . . . ?
N1 C10 C15 C20 174.2(3) . . . . ?
N1 C11 C17 N2 8.0(6) . . . . ?
N1 C11 C17 C24 -174.1(4) . . . . ?
C1 C28 C5 N1 26.5(4) . . . . ?
C1 C28 C5 C3 -101.1(4) . . . . ?
C1 C28 C9 O2 -171.5(4) . . . . ?
C1 C28 C9 C7 6.4(5) . . . . ?
C1 C15 C20 O4 168.3(4) . . . . ?
C1 C15 C20 N3 -11.7(6) . . . . ?
N2 C17 C24 C16 179.6(4) . . . . ?
C28 C1 C15 C10 -12.9(5) . . . . ?
C28 C1 C15 C20 177.7(3) . . . . ?
C3 C6 C26 C22 32.1(7) . . . . ?
C4 C11 C17 N2 -179.1(4) . . . . ?
C4 C11 C17 C24 -1.2(6) . . . . ?
C5 N1 C10 N5 -161.6(3) . . . . ?
C5 N1 C10 C15 21.2(5) . . . . ?
C5 N1 C11 C4 -128.6(4) . . . . ?
C5 N1 C11 C17 44.2(5) . . . . ?
C5 C28 C9 O2 4.9(5) . . . . ?
C5 C28 C9 C7 -177.2(3) . . . . ?
C5 C3 C6 O3 2.3(7) . . . . ?
C5 C3 C6 C26 -179.5(4) . . . . ?
C5 C3 C21 N2 -7.7(6) . . . . ?
C5 C3 C21 C13 173.2(4) . . . . ?
C6 C3 C5 N1 -120.2(4) . . . . ?
C6 C3 C5 C28 6.8(6) . . . . ?
C6 C3 C21 N2 175.3(4) . . . . ?
C6 C3 C21 C13 -3.8(6) . . . . ?
C7 C8 C23 C19 2.2(6) . . . . ?
C8 C7 C9 O2 -118.0(4) . . . . ?
C8 C7 C9 C28 64.0(5) . . . . ?
C8 C7 C14 C12 -1.4(6) . . . . ?
C9 C28 C5 N1 -150.0(3) . . . . ?
C9 C28 C5 C3 82.3(4) . . . . ?
C9 C7 C8 O1 -3.3(6) . . . . ?
C9 C7 C8 C23 175.1(4) . . . . ?
C9 C7 C14 C12 -177.3(4) . . . . ?
C10 N1 C5 C28 -35.6(4) . . . . ?
C10 N1 C5 C3 96.2(4) . . . . ?
C10 N1 C11 C4 45.5(5) . . . . ?
C10 N1 C11 C17 -141.7(4) . . . . ?
C10 C15 C20 O4 -0.7(6) . . . . ?
C10 C15 C20 N3 179.3(4) . . . . ?
C11 N1 C5 C28 138.5(3) . . . . ?
C11 N1 C5 C3 -89.6(4) . . . . ?
C11 N1 C10 N5 24.6(5) . . . . ?
C11 N1 C10 C15 -152.6(4) . . . . ?
C11 C4 C18 C16 0.0(7) . . . . ?
C11 C17 C24 C16 1.5(7) . . . . ?
C12 C19 C23 C8 -1.7(7) . . . . ?
C13 C22 C26 C6 -51.7(6) . . . . ?
C14 C7 C8 O1 -179.0(4) . . . . ?
C14 C7 C8 C23 -0.6(6) . . . . ?
C14 C7 C9 O2 57.7(5) . . . . ?
C14 C7 C9 C28 -120.2(4) . . . . ?
C14 C12 C19 C23 -0.3(7) . . . . ?
C15 C1 C28 C5 -4.4(5) . . . . ?
C15 C1 C28 C9 171.9(3) . . . . ?
C17 N2 C21 C3 -13.3(8) . . . . ?
C17 N2 C21 C13 165.8(5) . . . . ?
C18 C4 C11 N1 173.3(4) . . . . ?
C18 C4 C11 C17 0.4(6) . . . . ?
C18 C16 C24 C17 -1.0(7) . . . . ?
C19 C12 C14 C7 1.8(6) . . . . ?
C21 N2 C17 C11 -10.9(8) . . . . ?
C21 N2 C17 C24 171.1(5) . . . . ?
C21 C3 C5 N1 62.9(4) . . . . ?
C21 C3 C5 C28 -170.0(3) . . . . ?
C21 C3 C6 O3 179.1(4) . . . . ?
C21 C3 C6 C26 -2.7(6) . . . . ?
C21 C13 C22 C25 166.1(5) . . . . ?
C21 C13 C22 C26 45.0(6) . . . . ?
C21 C13 C22 C27 -74.3(6) . . . . ?
C22 C13 C21 N2 161.8(4) . . . . ?
C22 C13 C21 C3 -19.0(7) . . . . ?
C24 C16 C18 C4 0.3(7) . . . . ?
C25 C22 C26 C6 -172.8(5) . . . . ?
C27 C22 C26 C6 68.1(6) . . . . ?

_submission_special_instructions 'No special instructions were received'
