# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_c17058
_database_code_depnum_ccdc_archive 'CCDC 1998517'
loop_
_audit_author_name
_audit_author_address
'Sean Parkin'
;UKy
United States of America
;
# CIF edited on-the-fly by script CIFFIX (S. Parkin, 2000-2017). 
# CIFFIX: http://xray.uky.edu/people/parkin/programs/ciffix 
_audit_update_record             
;
2020-04-22 deposited with the CCDC.	2020-06-16 downloaded from the CCDC.
;

_audit_creation_method           'SHELXL-2017 and CIFFIX/1'

_shelx_SHELXL_version_number     2017/1

_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C28 H28 N2 O6) C H2 Cl2'
_chemical_formula_sum            'C57 H58 Cl2 N4 O12'
_chemical_formula_weight         1061.97

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_H-M_alt        'C 2'
_space_group_name_Hall           'C 2y'

_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'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'

_cell_length_a                   23.791(2)
_cell_length_b                   6.7169(6)
_cell_length_c                   17.0032(16)
_cell_angle_alpha                90
_cell_angle_beta                 103.374(4)
_cell_angle_gamma                90
_cell_volume                     2643.5(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    90.0(2)
_cell_measurement_reflns_used    9842
_cell_measurement_theta_min      3.82
_cell_measurement_theta_max      74.59

_exptl_crystal_description       needle
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.334
_exptl_crystal_F_000             1116
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.030
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    1.663
_shelx_estimated_absorpt_T_min   0.635
_shelx_estimated_absorpt_T_max   0.967
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.760
_exptl_absorpt_correction_T_max  0.929
_exptl_absorpt_process_details   'SADABS (Krause et al., 2015)'
_exptl_absorpt_special_details   
; 
In addition to absorption, multi-scan techniques also correct other slowly 
varying changes in scale factor over reciprocal space, such as those caused 
by x-ray beam inhomogeneity, goniometer imperfection, crystal decomposition, 
crystal longer than the x-ray beam cross section, absorption by the crystal 
mount etc.  These account, by and large, for much of the difference between 
estimated values of Tmin and Tmax and the _exptl_absorpt_correction_ values. 
;

_exptl_special_details           
; 
The crystal was mounted using polyisobutene oil on the tip of a fine glass 
fibre, which was fastened in a copper mounting pin with electrical solder. 
It was placed directly into the cold gas stream of a liquid-nitrogen based 
cryostat (Hope, 1994; Parkin & Hope, 1998). 
 
Diffraction data were collected with the crystal at 90K, which is standard 
practice in this laboratory for the majority of flash-cooled crystals. 
;

_diffrn_ambient_temperature      90.0(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   microsource
_diffrn_measurement_device_type  'Bruker D8 Venture dual source'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 5.6
_diffrn_reflns_number            25456
_diffrn_reflns_av_unetI/netI     0.0541
_diffrn_reflns_av_R_equivalents  0.0610
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.671
_diffrn_reflns_theta_max         74.520
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measured_fraction_theta_full 0.976
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_Laue_measured_fraction_full 0.976
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_point_group_measured_fraction_full 0.973

_reflns_number_total             5266
_reflns_number_gt                4832
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.823
_reflns_Friedel_fraction_max     0.959
_reflns_Friedel_fraction_full    0.969
_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       'APEX3 (Bruker-AXS, 2016)'
_computing_cell_refinement       'APEX3 (Bruker-AXS, 2016)'
_computing_data_reduction        'APEX3 (Bruker-AXS, 2016)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015a)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2015b)'
_computing_molecular_graphics    'XP in SHELXTL (Sheldrick, 2008)'
_computing_publication_material  
'SHELX (Sheldrick, 2008) and CIFFIX (Parkin, 2013)'

_refine_special_details          
; 
Refinement progress was checked using Platon (Spek, 2009) and by 
an R-tensor (Parkin, 2000). The final model was further checked 
with the IUCr utility checkCIF. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0417P)²+1.4710P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
; 
Flack 'x' determined using 2011 quotients [(I+)-(I-)]/[(I+)+(I-)] 
[Parsons, Flack and Wagner (2013)]. 
;
_refine_ls_abs_structure_Flack   0.068(14)
_chemical_absolute_configuration ad
# Might have been a tiny amount of an inverted twin component. 
_refine_ls_number_reflns         5266
_refine_ls_number_parameters     367
_refine_ls_number_restraints     86
_refine_ls_R_factor_all          0.0427
_refine_ls_R_factor_gt           0.0380
_refine_ls_wR_factor_ref         0.1008
_refine_ls_wR_factor_gt          0.0975
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.041
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.24018(8) 0.7694(5) 0.68077(12) 0.0230(4) Uani 1 1 d . . . . .
N2 N 0.42556(9) 0.5283(5) 0.66969(12) 0.0224(5) Uani 1 1 d . . . . .
H2 H 0.399931 0.431529 0.662616 0.027 Uiso 1 1 calc R U . . .
O1 O 0.35387(10) 0.4930(5) 0.51625(12) 0.0383(5) Uani 1 1 d . . . . .
O2 O 0.38716(7) 0.7856(5) 0.48027(10) 0.0258(4) Uani 1 1 d . . . . .
O3 O 0.17681(7) 0.7960(4) 0.32539(11) 0.0266(4) Uani 1 1 d . . . . .
O4 O 0.29830(8) 0.7431(5) 0.09829(11) 0.0351(5) Uani 1 1 d . . . . .
O5 O 0.51199(8) 0.6427(5) 0.74113(11) 0.0280(4) Uani 1 1 d . . . . .
O6 O 0.47311(7) 0.3523(4) 0.77435(11) 0.0265(4) Uani 1 1 d . . . . .
C1 C 0.27142(10) 0.7590(5) 0.75936(14) 0.0223(5) Uani 1 1 d . . . . .
C2 C 0.25243(11) 0.7379(5) 0.83086(15) 0.0247(5) Uani 1 1 d . . . . .
H2A H 0.212521 0.725660 0.830069 0.030 Uiso 1 1 calc R U . . .
C3 C 0.29393(12) 0.7355(5) 0.90268(15) 0.0274(6) Uani 1 1 d . . . . .
H3 H 0.282436 0.720982 0.952288 0.033 Uiso 1 1 calc R U . . .
C4 C 0.35304(12) 0.7541(6) 0.90347(15) 0.0283(6) Uani 1 1 d . . . . .
H4 H 0.380729 0.751002 0.953659 0.034 Uiso 1 1 calc R U . . .
C5 C 0.37154(11) 0.7769(6) 0.83278(15) 0.0253(5) Uani 1 1 d . . . . .
H5 H 0.411570 0.787256 0.834113 0.030 Uiso 1 1 calc R U . . .
C6 C 0.33051(10) 0.7844(5) 0.75917(14) 0.0224(5) Uani 1 1 d . . . . .
C7 C 0.33317(11) 0.8204(5) 0.67692(15) 0.0221(5) Uani 1 1 d . . . . .
C8 C 0.27752(11) 0.8095(5) 0.63192(15) 0.0235(5) Uani 1 1 d . . . . .
H8 H 0.266278 0.827091 0.574994 0.028 Uiso 1 1 calc R U . . .
C9 C 0.17741(10) 0.7597(6) 0.65606(16) 0.0265(5) Uani 1 1 d . . . . .
H9A H 0.165526 0.746310 0.597145 0.040 Uiso 1 1 calc R U . . .
H9B H 0.160844 0.881750 0.672800 0.040 Uiso 1 1 calc R U . . .
H9C H 0.163632 0.644528 0.681592 0.040 Uiso 1 1 calc R U . . .
C10 C 0.38672(11) 0.8755(5) 0.64940(15) 0.0245(6) Uani 1 1 d . . . . .
H10A H 0.414677 0.936564 0.695342 0.029 Uiso 1 1 calc R U . . .
H10B H 0.376510 0.977402 0.606377 0.029 Uiso 1 1 calc R U . . .
C11 C 0.41652(10) 0.6989(5) 0.61685(14) 0.0217(5) Uani 1 1 d . . . . .
H11 H 0.455256 0.745700 0.611046 0.026 Uiso 1 1 calc R U . . .
C12 C 0.38219(10) 0.6391(5) 0.53398(15) 0.0225(5) Uani 1 1 d . . . . .
C13 C 0.35676(10) 0.7672(5) 0.39981(14) 0.0220(5) Uani 1 1 d . . . . .
C14 C 0.29682(10) 0.7719(5) 0.37897(14) 0.0221(5) Uani 1 1 d . . . . .
H14 H 0.275250 0.778157 0.419454 0.027 Uiso 1 1 calc R U . . .
C15 C 0.26913(10) 0.7671(5) 0.29766(14) 0.0200(5) Uani 1 1 d . . . . .
C16 C 0.2046(1) 0.7774(5) 0.27350(14) 0.0214(5) Uani 1 1 d . . . . .
C17 C 0.17703(10) 0.7656(5) 0.18727(15) 0.0244(5) Uani 1 1 d . . . . .
H17 H 0.136027 0.768275 0.171659 0.029 Uiso 1 1 calc R U . . .
C18 C 0.20645(11) 0.7513(5) 0.12900(14) 0.0243(5) Uani 1 1 d . . . . .
C19 C 0.17823(12) 0.7390(6) 0.04066(15) 0.0303(6) Uani 1 1 d . . . . .
H19A H 0.188430 0.856919 0.012988 0.046 Uiso 1 1 calc R U . . .
H19B H 0.136198 0.732962 0.033570 0.046 Uiso 1 1 calc R U . . .
H19C H 0.191614 0.619097 0.017674 0.046 Uiso 1 1 calc R U . . .
C20 C 0.27096(11) 0.7500(6) 0.15053(14) 0.0245(5) Uani 1 1 d . . . . .
C21 C 0.3008(1) 0.7578(5) 0.23772(14) 0.0211(5) Uani 1 1 d . . . . .
C22 C 0.36113(10) 0.7561(5) 0.26061(14) 0.0228(5) Uani 1 1 d . . . . .
H22 H 0.382998 0.751773 0.220440 0.027 Uiso 1 1 calc R U . . .
C23 C 0.38907(10) 0.7608(5) 0.34140(14) 0.0231(5) Uani 1 1 d . . . . .
H23 H 0.430080 0.759547 0.356939 0.028 Uiso 1 1 calc R U . . .
C24 C 0.4734(1) 0.5178(6) 0.72986(15) 0.0225(5) Uani 1 1 d . . . . .
C25 C 0.52223(11) 0.3092(6) 0.84310(15) 0.0257(6) Uani 1 1 d . . . . .
C26 C 0.57632(11) 0.2711(6) 0.81269(17) 0.0321(6) Uani 1 1 d . . . . .
H26A H 0.568935 0.164253 0.772375 0.048 Uiso 1 1 calc R U . . .
H26B H 0.607868 0.231731 0.858045 0.048 Uiso 1 1 calc R U . . .
H26C H 0.587127 0.392791 0.787983 0.048 Uiso 1 1 calc R U . . .
C27 C 0.52963(14) 0.4775(6) 0.90477(17) 0.0364(7) Uani 1 1 d . . . . .
H27A H 0.544970 0.595461 0.882979 0.055 Uiso 1 1 calc R U . . .
H27B H 0.556566 0.435831 0.954796 0.055 Uiso 1 1 calc R U . . .
H27C H 0.492124 0.509547 0.916191 0.055 Uiso 1 1 calc R U . . .
C28 C 0.50350(13) 0.1193(6) 0.87751(19) 0.0375(7) Uani 1 1 d . . . . .
H28A H 0.496984 0.015387 0.835939 0.056 Uiso 1 1 calc R U . . .
H28B H 0.467636 0.143429 0.895025 0.056 Uiso 1 1 calc R U . . .
H28C H 0.533738 0.076158 0.923853 0.056 Uiso 1 1 calc R U . . .
C1S C 0.4803(4) 0.1769(14) 0.5129(3) 0.0437(19) Uani 0.399(4) 1 d D U P A -1
H1S1 H 0.441092 0.199348 0.521617 0.052 Uiso 0.399(4) 1 calc R U P A -1
H1S2 H 0.492948 0.041716 0.532600 0.052 Uiso 0.399(4) 1 calc R U P A -1
Cl1S Cl 0.5282(4) 0.3549(16) 0.5674(3) 0.0822(19) Uani 0.399(4) 1 d D U P A -1
Cl2S Cl 0.47873(17) 0.1950(6) 0.40917(16) 0.0624(10) Uani 0.399(4) 1 d D U P A
-1
C1S' C 0.504(2) 0.459(3) 0.5088(13) 0.0437(19) Uani 0.101(4) 1 d D U P A -2
H1S3 H 0.478374 0.554338 0.527792 0.052 Uiso 0.101(4) 1 calc R U P A -2
H1S4 H 0.537178 0.534493 0.497568 0.052 Uiso 0.101(4) 1 calc R U P A -2
Cl1' Cl 0.5295(15) 0.280(4) 0.5844(11) 0.0822(19) Uani 0.101(4) 1 d D U P A -2
Cl2' Cl 0.4662(11) 0.341(4) 0.420(1) 0.0624(10) Uani 0.101(4) 1 d D 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
N1 C1 1.372(3) . ?
N1 C8 1.376(3) . ?
N1 C9 1.456(3) . ?
N2 C24 1.345(3) . ?
N2 C11 1.442(3) . ?
N2 H2 0.8800 . ?
O1 C12 1.189(4) . ?
O2 C12 1.366(3) . ?
O2 C13 1.397(3) . ?
O3 C16 1.225(3) . ?
O4 C20 1.217(3) . ?
O5 C24 1.226(3) . ?
O6 C24 1.345(3) . ?
O6 C25 1.478(3) . ?
C1 C2 1.399(3) . ?
C1 C6 1.417(3) . ?
C2 C3 1.382(4) . ?
C2 H2A 0.9500 . ?
C3 C4 1.409(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.381(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.399(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.435(3) . ?
C7 C8 1.369(4) . ?
C7 C10 1.502(3) . ?
C8 H8 0.9500 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C11 1.548(4) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.510(3) . ?
C11 H11 1.0000 . ?
C13 C14 1.388(3) . ?
C13 C23 1.390(3) . ?
C14 C15 1.387(3) . ?
C14 H14 0.9500 . ?
C15 C21 1.402(3) . ?
C15 C16 1.496(3) . ?
C16 C17 1.463(3) . ?
C17 C18 1.342(4) . ?
C17 H17 0.9500 . ?
C18 C20 1.493(3) . ?
C18 C19 1.499(3) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 C21 1.489(3) . ?
C21 C22 1.397(3) . ?
C22 C23 1.381(3) . ?
C22 H22 0.9500 . ?
C23 H23 0.9500 . ?
C25 C28 1.513(4) . ?
C25 C26 1.516(4) . ?
C25 C27 1.524(4) . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
C1S Cl1S 1.760(6) . ?
C1S Cl2S 1.760(6) . ?
C1S H1S1 0.9900 . ?
C1S H1S2 0.9900 . ?
C1S' Cl2' 1.760(6) . ?
C1S' Cl1' 1.760(6) . ?
C1S' H1S3 0.9900 . ?
C1S' H1S4 0.9900 . ?

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
C1 N1 C8 108.5(2) . . ?
C1 N1 C9 124.5(2) . . ?
C8 N1 C9 126.6(2) . . ?
C24 N2 C11 119.6(2) . . ?
C24 N2 H2 120.2 . . ?
C11 N2 H2 120.2 . . ?
C12 O2 C13 119.1(2) . . ?
C24 O6 C25 120.0(2) . . ?
N1 C1 C2 129.8(2) . . ?
N1 C1 C6 107.8(2) . . ?
C2 C1 C6 122.3(2) . . ?
C3 C2 C1 117.5(2) . . ?
C3 C2 H2A 121.3 . . ?
C1 C2 H2A 121.3 . . ?
C2 C3 C4 121.0(2) . . ?
C2 C3 H3 119.5 . . ?
C4 C3 H3 119.5 . . ?
C5 C4 C3 121.3(2) . . ?
C5 C4 H4 119.3 . . ?
C3 C4 H4 119.3 . . ?
C4 C5 C6 119.1(2) . . ?
C4 C5 H5 120.5 . . ?
C6 C5 H5 120.5 . . ?
C5 C6 C1 118.8(2) . . ?
C5 C6 C7 134.4(2) . . ?
C1 C6 C7 106.9(2) . . ?
C8 C7 C6 106.3(2) . . ?
C8 C7 C10 128.3(2) . . ?
C6 C7 C10 125.2(2) . . ?
C7 C8 N1 110.4(2) . . ?
C7 C8 H8 124.8 . . ?
N1 C8 H8 124.8 . . ?
N1 C9 H9A 109.5 . . ?
N1 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
N1 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C7 C10 C11 114.5(2) . . ?
C7 C10 H10A 108.6 . . ?
C11 C10 H10A 108.6 . . ?
C7 C10 H10B 108.6 . . ?
C11 C10 H10B 108.6 . . ?
H10A C10 H10B 107.6 . . ?
N2 C11 C12 109.9(2) . . ?
N2 C11 C10 113.6(2) . . ?
C12 C11 C10 110.1(2) . . ?
N2 C11 H11 107.7 . . ?
C12 C11 H11 107.7 . . ?
C10 C11 H11 107.7 . . ?
O1 C12 O2 123.8(2) . . ?
O1 C12 C11 127.5(2) . . ?
O2 C12 C11 108.7(2) . . ?
C14 C13 C23 121.6(2) . . ?
C14 C13 O2 121.1(2) . . ?
C23 C13 O2 117.1(2) . . ?
C15 C14 C13 118.5(2) . . ?
C15 C14 H14 120.8 . . ?
C13 C14 H14 120.8 . . ?
C14 C15 C21 120.9(2) . . ?
C14 C15 C16 119.5(2) . . ?
C21 C15 C16 119.5(2) . . ?
O3 C16 C17 122.4(2) . . ?
O3 C16 C15 119.8(2) . . ?
C17 C16 C15 117.8(2) . . ?
C18 C17 C16 123.6(2) . . ?
C18 C17 H17 118.2 . . ?
C16 C17 H17 118.2 . . ?
C17 C18 C20 120.1(2) . . ?
C17 C18 C19 123.7(2) . . ?
C20 C18 C19 116.2(2) . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
O4 C20 C21 121.0(2) . . ?
O4 C20 C18 120.9(2) . . ?
C21 C20 C18 118.0(2) . . ?
C22 C21 C15 119.2(2) . . ?
C22 C21 C20 120.0(2) . . ?
C15 C21 C20 120.8(2) . . ?
C23 C22 C21 120.3(2) . . ?
C23 C22 H22 119.9 . . ?
C21 C22 H22 119.9 . . ?
C22 C23 C13 119.5(2) . . ?
C22 C23 H23 120.2 . . ?
C13 C23 H23 120.2 . . ?
O5 C24 N2 123.7(3) . . ?
O5 C24 O6 125.4(2) . . ?
N2 C24 O6 110.9(2) . . ?
O6 C25 C28 102.8(2) . . ?
O6 C25 C26 110.0(2) . . ?
C28 C25 C26 109.8(3) . . ?
O6 C25 C27 110.1(2) . . ?
C28 C25 C27 110.9(2) . . ?
C26 C25 C27 112.8(2) . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C25 C27 H27A 109.5 . . ?
C25 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C25 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C25 C28 H28A 109.5 . . ?
C25 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C25 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
Cl1S C1S Cl2S 110.0(5) . . ?
Cl1S C1S H1S1 109.7 . . ?
Cl2S C1S H1S1 109.7 . . ?
Cl1S C1S H1S2 109.7 . . ?
Cl2S C1S H1S2 109.7 . . ?
H1S1 C1S H1S2 108.2 . . ?
Cl2' C1S' Cl1' 109.9(5) . . ?
Cl2' C1S' H1S3 109.7 . . ?
Cl1' C1S' H1S3 109.7 . . ?
Cl2' C1S' H1S4 109.7 . . ?
Cl1' C1S' H1S4 109.7 . . ?
H1S3 C1S' H1S4 108.2 . . ?

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
C8 N1 C1 C2 174.2(3) . . . . ?
C9 N1 C1 C2 0.0(5) . . . . ?
C8 N1 C1 C6 -2.7(3) . . . . ?
C9 N1 C1 C6 -176.9(3) . . . . ?
N1 C1 C2 C3 -178.8(3) . . . . ?
C6 C1 C2 C3 -2.2(4) . . . . ?
C1 C2 C3 C4 0.2(4) . . . . ?
C2 C3 C4 C5 0.5(5) . . . . ?
C3 C4 C5 C6 1.0(5) . . . . ?
C4 C5 C6 C1 -2.9(4) . . . . ?
C4 C5 C6 C7 174.5(3) . . . . ?
N1 C1 C6 C5 -179.1(3) . . . . ?
C2 C1 C6 C5 3.7(4) . . . . ?
N1 C1 C6 C7 2.8(3) . . . . ?
C2 C1 C6 C7 -174.5(3) . . . . ?
C5 C6 C7 C8 -179.5(3) . . . . ?
C1 C6 C7 C8 -1.8(3) . . . . ?
C5 C6 C7 C10 -4.0(5) . . . . ?
C1 C6 C7 C10 173.7(3) . . . . ?
C6 C7 C8 N1 0.2(3) . . . . ?
C10 C7 C8 N1 -175.1(3) . . . . ?
C1 N1 C8 C7 1.6(3) . . . . ?
C9 N1 C8 C7 175.7(3) . . . . ?
C8 C7 C10 C11 -87.3(3) . . . . ?
C6 C7 C10 C11 98.3(3) . . . . ?
C24 N2 C11 C12 149.9(2) . . . . ?
C24 N2 C11 C10 -86.2(3) . . . . ?
C7 C10 C11 N2 -49.5(3) . . . . ?
C7 C10 C11 C12 74.3(3) . . . . ?
C13 O2 C12 O1 1.1(4) . . . . ?
C13 O2 C12 C11 -177.2(2) . . . . ?
N2 C11 C12 O1 17.6(4) . . . . ?
C10 C11 C12 O1 -108.3(3) . . . . ?
N2 C11 C12 O2 -164.1(2) . . . . ?
C10 C11 C12 O2 69.9(2) . . . . ?
C12 O2 C13 C14 65.8(4) . . . . ?
C12 O2 C13 C23 -119.4(3) . . . . ?
C23 C13 C14 C15 0.9(4) . . . . ?
O2 C13 C14 C15 175.5(2) . . . . ?
C13 C14 C15 C21 0.0(4) . . . . ?
C13 C14 C15 C16 -178.4(3) . . . . ?
C14 C15 C16 O3 2.2(4) . . . . ?
C21 C15 C16 O3 -176.2(3) . . . . ?
C14 C15 C16 C17 -178.1(2) . . . . ?
C21 C15 C16 C17 3.5(4) . . . . ?
O3 C16 C17 C18 177.9(3) . . . . ?
C15 C16 C17 C18 -1.8(4) . . . . ?
C16 C17 C18 C20 -1.0(4) . . . . ?
C16 C17 C18 C19 179.9(3) . . . . ?
C17 C18 C20 O4 -177.8(3) . . . . ?
C19 C18 C20 O4 1.4(4) . . . . ?
C17 C18 C20 C21 2.1(4) . . . . ?
C19 C18 C20 C21 -178.8(2) . . . . ?
C14 C15 C21 C22 -0.9(4) . . . . ?
C16 C15 C21 C22 177.5(3) . . . . ?
C14 C15 C21 C20 179.2(3) . . . . ?
C16 C15 C21 C20 -2.5(4) . . . . ?
O4 C20 C21 C22 -0.4(5) . . . . ?
C18 C20 C21 C22 179.8(3) . . . . ?
O4 C20 C21 C15 179.6(3) . . . . ?
C18 C20 C21 C15 -0.3(4) . . . . ?
C15 C21 C22 C23 0.9(4) . . . . ?
C20 C21 C22 C23 -179.2(3) . . . . ?
C21 C22 C23 C13 0.0(4) . . . . ?
C14 C13 C23 C22 -0.9(5) . . . . ?
O2 C13 C23 C22 -175.7(2) . . . . ?
C11 N2 C24 O5 -3.2(4) . . . . ?
C11 N2 C24 O6 177.6(2) . . . . ?
C25 O6 C24 O5 -0.2(4) . . . . ?
C25 O6 C24 N2 179.0(2) . . . . ?
C24 O6 C25 C28 177.7(2) . . . . ?
C24 O6 C25 C26 -65.4(3) . . . . ?
C24 O6 C25 C27 59.5(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N2 H2 O3 0.88 2.09 2.910(3) 154.3 4_546 yes
C9 H9A O1 0.98 2.50 3.254(3) 133.2 4_556 yes
C23 H23 O5 0.95 2.52 3.109(3) 120.1 2_656 yes
C26 H26C O5 0.98 2.45 3.032(4) 117.9 . yes
C27 H27A O5 0.98 2.38 2.934(4) 115.3 . yes

_refine_diff_density_max         0.488
_refine_diff_density_min         -0.298
_refine_diff_density_rms         0.040

