# Electronic Supplementary Material (ESI) for Physical Chemistry Chemical Physics.
# This journal is © the Owner Societies 2021

####################################################################### 
# 
# 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_a
_database_code_depnum_ccdc_archive 'CCDC 2043353'
loop_
_audit_author_name
_audit_author_address
'Andrei Churakov'
;Institute of General and Inorganic Chemistry RAS
Russia
;
_audit_update_record             
;
2020-11-09 deposited with the CCDC.	2021-05-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C18 H14 Cl4 N2 O), C4 H6 O4'
_chemical_formula_sum            'C40 H34 Cl8 N4 O6'
_chemical_formula_weight         950.31

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   8.0830(3)
_cell_length_b                   9.0956(3)
_cell_length_c                   15.0054(6)
_cell_angle_alpha                82.8035(14)
_cell_angle_beta                 80.0928(13)
_cell_angle_gamma                71.2636(12)
_cell_volume                     1026.25(7)
_cell_formula_units_Z            1
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    9951
_cell_measurement_theta_min      2.371
_cell_measurement_theta_max      30.532

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.538
_exptl_crystal_F_000             486
_exptl_transmission_factor_min   0.7592
_exptl_transmission_factor_max   0.8622
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.602
_shelx_estimated_absorpt_T_min   0.817
_shelx_estimated_absorpt_T_max   0.942
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   'SADABS (Bruker, 2016)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker SMART APEX II'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16369
_diffrn_reflns_av_unetI/netI     0.0293
_diffrn_reflns_av_R_equivalents  0.0278
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.371
_diffrn_reflns_theta_max         27.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             4921
_reflns_number_gt                4366
_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       'APEX3 (Bruker, 2018)'
_computing_cell_refinement       'SAINT (Bruker, 2018)'
_computing_data_reduction        'SAINT (Bruker, 2018)'
_computing_structure_solution    'SHELXT (Sheldrick, 2016)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0510P)²+0.3145P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     difmap
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4921
_refine_ls_number_parameters     330
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0382
_refine_ls_R_factor_gt           0.0335
_refine_ls_wR_factor_ref         0.0899
_refine_ls_wR_factor_gt          0.0869
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_restrained_S_all      1.062
_refine_ls_shift/su_max          0.001
_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
O1 O 0.31595(13) 0.73463(12) 0.27039(7) 0.0157(2) Uani 1 1 d . . . . .
N1 N 0.45783(16) 0.53095(14) 0.11404(8) 0.0147(2) Uani 1 1 d . . . . .
N2 N 0.30799(16) 0.38336(14) 0.08338(8) 0.0179(3) Uani 1 1 d . . . . .
Cl1 Cl 0.89606(4) 0.54348(4) 0.19996(3) 0.02078(10) Uani 1 1 d . . . . .
Cl2 Cl 0.92009(5) 1.09653(5) 0.27924(3) 0.02570(10) Uani 1 1 d . . . . .
Cl3 Cl 0.27508(5) 0.60591(5) 0.56765(2) 0.02262(10) Uani 1 1 d . . . . .
Cl4 Cl 0.17742(6) 0.08144(5) 0.48891(3) 0.02745(11) Uani 1 1 d . . . . .
C11 C 0.49689(18) 0.67777(16) 0.23246(9) 0.0138(3) Uani 1 1 d . . . . .
C12 C 0.50036(19) 0.66850(16) 0.13096(9) 0.0152(3) Uani 1 1 d . . . . .
C13 C 0.5623(2) 0.37814(17) 0.12554(10) 0.0189(3) Uani 1 1 d . . . . .
C14 C 0.4691(2) 0.28863(17) 0.10615(10) 0.0193(3) Uani 1 1 d . . . . .
C15 C 0.30707(19) 0.52684(17) 0.08880(9) 0.0159(3) Uani 1 1 d . . . . .
C21 C 0.60158(18) 0.78267(16) 0.24681(9) 0.0144(3) Uani 1 1 d . . . . .
C22 C 0.51915(19) 0.93349(17) 0.27326(10) 0.0176(3) Uani 1 1 d . . . . .
C23 C 0.6155(2) 1.03032(17) 0.28481(10) 0.0192(3) Uani 1 1 d . . . . .
C24 C 0.7980(2) 0.97479(17) 0.26839(10) 0.0182(3) Uani 1 1 d . . . . .
C25 C 0.88650(19) 0.82515(17) 0.24274(10) 0.0178(3) Uani 1 1 d . . . . .
C26 C 0.78598(19) 0.73115(16) 0.23253(9) 0.0153(3) Uani 1 1 d . . . . .
C31 C 0.26019(18) 0.54986(17) 0.39650(10) 0.0155(3) Uani 1 1 d . . . . .
C32 C 0.23752(19) 0.45726(17) 0.33496(10) 0.0164(3) Uani 1 1 d . . . . .
C33 C 0.21063(19) 0.31406(17) 0.36256(10) 0.0180(3) Uani 1 1 d . . . . .
C34 C 0.20824(19) 0.26120(17) 0.45329(10) 0.0191(3) Uani 1 1 d . . . . .
C35 C 0.2289(2) 0.34994(18) 0.51690(10) 0.0194(3) Uani 1 1 d . . . . .
C36 C 0.25356(19) 0.49312(17) 0.48733(10) 0.0173(3) Uani 1 1 d . . . . .
C37 C 0.2859(2) 0.70716(18) 0.36687(10) 0.0174(3) Uani 1 1 d . . . . .
H10 H 0.548(2) 0.5739(19) 0.2598(11) 0.011(4) Uiso 1 1 d . . . . .
H13 H 0.674(3) 0.355(2) 0.1426(13) 0.027(5) Uiso 1 1 d . . . . .
H14 H 0.503(3) 0.178(2) 0.1064(14) 0.030(5) Uiso 1 1 d . . . . .
H15 H 0.212(3) 0.620(2) 0.0757(12) 0.021(4) Uiso 1 1 d . . . . .
H22 H 0.392(3) 0.972(2) 0.2802(14) 0.033(5) Uiso 1 1 d . . . . .
H23 H 0.556(2) 1.133(2) 0.3041(12) 0.022(5) Uiso 1 1 d . . . . .
H25 H 1.011(3) 0.788(2) 0.2317(13) 0.025(5) Uiso 1 1 d . . . . .
H32 H 0.232(2) 0.493(2) 0.2758(12) 0.017(4) Uiso 1 1 d . . . . .
H33 H 0.198(2) 0.253(2) 0.3182(13) 0.023(5) Uiso 1 1 d . . . . .
H35 H 0.230(3) 0.318(2) 0.5766(14) 0.033(5) Uiso 1 1 d . . . . .
H121 H 0.413(2) 0.763(2) 0.1085(11) 0.014(4) Uiso 1 1 d . . . . .
H122 H 0.616(2) 0.6616(19) 0.0985(11) 0.013(4) Uiso 1 1 d . . . . .
H371 H 0.380(3) 0.717(2) 0.3935(13) 0.028(5) Uiso 1 1 d . . . . .
H372 H 0.183(3) 0.791(2) 0.3875(13) 0.025(5) Uiso 1 1 d . . . . .
O11 O 0.05939(16) 0.29145(13) 0.03849(9) 0.0269(3) Uani 1 1 d . . . . .
O12 O 0.24894(17) 0.05222(15) 0.05526(11) 0.0399(3) Uani 1 1 d . . . . .
C16 C 0.1109(2) 0.13911(17) 0.03504(11) 0.0204(3) Uani 1 1 d . . . . .
C17 C -0.0252(2) 0.08617(18) 0.00178(12) 0.0234(3) Uani 1 1 d . . . . .
H11 H 0.139(4) 0.317(3) 0.0548(17) 0.054(7) Uiso 1 1 d . . . . .
H16 H -0.049(3) 0.143(3) -0.0624(16) 0.044(6) Uiso 1 1 d . . . . .
H17 H -0.133(3) 0.122(3) 0.0396(16) 0.043(6) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C11 1.4253(16) . ?
O1 C37 1.4300(17) . ?
N1 C15 1.3497(18) . ?
N1 C13 1.3823(18) . ?
N1 C12 1.4607(18) . ?
N2 C15 1.3153(19) . ?
N2 C14 1.383(2) . ?
Cl1 C26 1.7402(14) . ?
Cl2 C24 1.7403(15) . ?
Cl3 C36 1.7413(15) . ?
Cl4 C34 1.7372(15) . ?
C11 C21 1.5184(19) . ?
C11 C12 1.5309(19) . ?
C11 H10 0.971(16) . ?
C12 H121 0.983(17) . ?
C12 H122 0.961(17) . ?
C13 C14 1.358(2) . ?
C13 H13 0.93(2) . ?
C14 H14 0.95(2) . ?
C15 H15 0.968(19) . ?
C21 C22 1.393(2) . ?
C21 C26 1.3978(19) . ?
C22 C23 1.392(2) . ?
C22 H22 0.96(2) . ?
C23 C24 1.385(2) . ?
C23 H23 0.960(19) . ?
C24 C25 1.387(2) . ?
C25 C26 1.392(2) . ?
C25 H25 0.94(2) . ?
C31 C36 1.394(2) . ?
C31 C32 1.396(2) . ?
C31 C37 1.512(2) . ?
C32 C33 1.390(2) . ?
C32 H32 0.909(18) . ?
C33 C34 1.385(2) . ?
C33 H33 0.957(19) . ?
C34 C35 1.387(2) . ?
C35 C36 1.387(2) . ?
C35 H35 0.91(2) . ?
C37 H371 0.95(2) . ?
C37 H372 0.96(2) . ?
O11 C16 1.3176(18) . ?
O11 H11 0.83(3) . ?
O12 C16 1.205(2) . ?
C16 C17 1.510(2) . ?
C17 C17 1.493(3) 2 ?
C17 H16 1.05(2) . ?
C17 H17 0.94(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C11 O1 C37 113.58(11) . . ?
C15 N1 C13 106.66(12) . . ?
C15 N1 C12 127.20(12) . . ?
C13 N1 C12 126.07(12) . . ?
C15 N2 C14 105.75(12) . . ?
O1 C11 C21 112.22(11) . . ?
O1 C11 C12 106.67(11) . . ?
C21 C11 C12 110.23(11) . . ?
O1 C11 H10 109.1(10) . . ?
C21 C11 H10 109.5(10) . . ?
C12 C11 H10 109.0(10) . . ?
N1 C12 C11 111.26(11) . . ?
N1 C12 H121 109.4(10) . . ?
C11 C12 H121 108.3(10) . . ?
N1 C12 H122 107.4(10) . . ?
C11 C12 H122 110.6(10) . . ?
H121 C12 H122 109.9(14) . . ?
C14 C13 N1 106.36(13) . . ?
C14 C13 H13 133.1(12) . . ?
N1 C13 H13 120.5(12) . . ?
C13 C14 N2 109.41(13) . . ?
C13 C14 H14 128.4(12) . . ?
N2 C14 H14 122.2(12) . . ?
N2 C15 N1 111.83(13) . . ?
N2 C15 H15 125.5(11) . . ?
N1 C15 H15 122.6(11) . . ?
C22 C21 C26 117.44(13) . . ?
C22 C21 C11 121.86(12) . . ?
C26 C21 C11 120.69(12) . . ?
C23 C22 C21 121.71(14) . . ?
C23 C22 H22 120.2(12) . . ?
C21 C22 H22 118.0(12) . . ?
C24 C23 C22 118.67(13) . . ?
C24 C23 H23 121.2(11) . . ?
C22 C23 H23 120.1(11) . . ?
C23 C24 C25 121.88(13) . . ?
C23 C24 Cl2 119.18(11) . . ?
C25 C24 Cl2 118.93(11) . . ?
C24 C25 C26 117.89(13) . . ?
C24 C25 H25 121.4(11) . . ?
C26 C25 H25 120.7(11) . . ?
C25 C26 C21 122.40(13) . . ?
C25 C26 Cl1 118.15(11) . . ?
C21 C26 Cl1 119.45(11) . . ?
C36 C31 C32 117.15(13) . . ?
C36 C31 C37 121.09(13) . . ?
C32 C31 C37 121.74(13) . . ?
C33 C32 C31 121.68(14) . . ?
C33 C32 H32 118.1(11) . . ?
C31 C32 H32 120.1(11) . . ?
C34 C33 C32 119.12(13) . . ?
C34 C33 H33 121.6(11) . . ?
C32 C33 H33 119.3(11) . . ?
C33 C34 C35 121.14(14) . . ?
C33 C34 Cl4 119.81(12) . . ?
C35 C34 Cl4 119.05(12) . . ?
C36 C35 C34 118.33(14) . . ?
C36 C35 H35 118.6(13) . . ?
C34 C35 H35 123.0(13) . . ?
C35 C36 C31 122.58(13) . . ?
C35 C36 Cl3 118.22(11) . . ?
C31 C36 Cl3 119.20(11) . . ?
O1 C37 C31 112.75(11) . . ?
O1 C37 H371 110.6(12) . . ?
C31 C37 H371 110.0(12) . . ?
O1 C37 H372 105.8(11) . . ?
C31 C37 H372 111.7(11) . . ?
H371 C37 H372 105.7(16) . . ?
C16 O11 H11 108.6(18) . . ?
O12 C16 O11 124.81(14) . . ?
O12 C16 C17 123.86(14) . . ?
O11 C16 C17 111.34(13) . . ?
C17 C17 C16 113.56(17) 2 . ?
C17 C17 H16 110.7(12) 2 . ?
C16 C17 H16 108.8(12) . . ?
C17 C17 H17 110.1(14) 2 . ?
C16 C17 H17 108.5(14) . . ?
H16 C17 H17 104.8(18) . . ?

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
O11 H11 N2 0.83(3) 1.79(3) 2.6222(17) 175(3) .

_refine_diff_density_max         0.463
_refine_diff_density_min         -0.254
_refine_diff_density_rms         0.064

####################################################################### 
# 
# 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_a_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2043355'
loop_
_audit_author_name
_audit_author_address
'Andrei Churakov'
;Institute of General and Inorganic Chemistry RAS
Russia
;
_audit_update_record             
;
2020-11-09 deposited with the CCDC.	2021-05-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H15 Cl4 N2 O, C4 H3 O4'
_chemical_formula_sum            'C22 H18 Cl4 N2 O5'
_chemical_formula_weight         532.18

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   8.8026(3)
_cell_length_b                   8.8626(3)
_cell_length_c                   29.7363(10)
_cell_angle_alpha                83.6323(10)
_cell_angle_beta                 85.5987(13)
_cell_angle_gamma                89.6660(12)
_cell_volume                     2298.73(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9892
_cell_measurement_theta_min      2.321
_cell_measurement_theta_max      30.498

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.538
_exptl_crystal_F_000             1088
_exptl_transmission_factor_min   0.6917
_exptl_transmission_factor_max   0.7461
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.553
_shelx_estimated_absorpt_T_min   0.830
_shelx_estimated_absorpt_T_max   0.947
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   'SADABS (Bruker, 2016)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker SMART APEX II'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            27453
_diffrn_reflns_av_unetI/netI     0.0389
_diffrn_reflns_av_R_equivalents  0.0260
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_theta_min         2.073
_diffrn_reflns_theta_max         28.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measured_fraction_theta_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_point_group_measured_fraction_full 0.986
_reflns_number_total             12011
_reflns_number_gt                10567
_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       'APEX3 (Bruker, 2018)'
_computing_cell_refinement       'SAINT (Bruker, 2018)'
_computing_data_reduction        'SAINT (Bruker, 2018)'
_computing_structure_solution    'SHELXT (Sheldrick, 2016)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0253P)²+5.9412P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     difmap
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_extinction_coef       0.0038(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         12011
_refine_ls_number_parameters     740
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0606
_refine_ls_R_factor_gt           0.0525
_refine_ls_wR_factor_ref         0.1222
_refine_ls_wR_factor_gt          0.1188
_refine_ls_goodness_of_fit_ref   1.106
_refine_ls_restrained_S_all      1.106
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.20944(19) 0.7420(2) 0.11797(6) 0.0141(3) Uani 1 1 d . . . . .
N11 N 0.3827(2) 0.5827(2) 0.05426(7) 0.0132(4) Uani 1 1 d . . . . .
N12 N 0.2546(3) 0.4135(2) 0.02619(7) 0.0152(4) Uani 1 1 d . . . . .
Cl11 Cl 0.69446(7) 0.74447(7) 0.15104(2) 0.01941(14) Uani 1 1 d . . . . .
Cl12 Cl 0.58712(8) 1.32908(7) 0.17725(2) 0.02303(15) Uani 1 1 d . . . . .
Cl13 Cl 0.31246(8) 0.55887(7) 0.24205(2) 0.02040(14) Uani 1 1 d . . . . .
Cl14 Cl 0.01047(8) 0.04888(7) 0.22223(2) 0.02158(14) Uani 1 1 d . . . . .
C11 C 0.3711(3) 0.7416(3) 0.11749(8) 0.0121(4) Uani 1 1 d . . . . .
C12 C 0.4277(3) 0.7279(3) 0.06833(9) 0.0154(5) Uani 1 1 d . . . . .
C13 C 0.4693(3) 0.4516(3) 0.05649(8) 0.0152(5) Uani 1 1 d . . . . .
C14 C 0.3887(3) 0.3457(3) 0.03883(9) 0.0164(5) Uani 1 1 d . . . . .
C15 C 0.2528(3) 0.5560(3) 0.03577(8) 0.0145(5) Uani 1 1 d . . . . .
C21 C 0.4294(3) 0.8886(3) 0.13211(8) 0.0130(4) Uani 1 1 d . . . . .
C22 C 0.3379(3) 1.0178(3) 0.12972(9) 0.0148(5) Uani 1 1 d . . . . .
C23 C 0.3866(3) 1.1541(3) 0.14283(9) 0.0157(5) Uani 1 1 d . . . . .
C24 C 0.5301(3) 1.1613(3) 0.15852(9) 0.0159(5) Uani 1 1 d . . . . .
C25 C 0.6267(3) 1.0362(3) 0.16068(9) 0.0153(5) Uani 1 1 d . . . . .
C26 C 0.5739(3) 0.9018(3) 0.14742(8) 0.0131(4) Uani 1 1 d . . . . .
C31 C 0.1136(3) 0.5451(3) 0.17674(8) 0.0137(5) Uani 1 1 d . . . . .
C32 C 0.0155(3) 0.4631(3) 0.15364(9) 0.0161(5) Uani 1 1 d . . . . .
C33 C -0.0158(3) 0.3104(3) 0.16694(9) 0.0166(5) Uani 1 1 d . . . . .
C34 C 0.0529(3) 0.2389(3) 0.20402(9) 0.0154(5) Uani 1 1 d . . . . .
C35 C 0.1556(3) 0.3143(3) 0.22659(9) 0.0158(5) Uani 1 1 d . . . . .
C36 C 0.1846(3) 0.4666(3) 0.21260(8) 0.0141(5) Uani 1 1 d . . . . .
C37 C 0.1331(3) 0.7127(3) 0.16251(9) 0.0156(5) Uani 1 1 d . . . . .
H10 H 0.184(5) 0.374(5) 0.0118(14) 0.045(12) Uiso 1 1 d . . . . .
H13 H 0.574(4) 0.441(4) 0.0682(13) 0.035(10) Uiso 1 1 d . . . . .
H14 H 0.416(4) 0.251(4) 0.0339(11) 0.021(8) Uiso 1 1 d . . . . .
H15 H 0.184(4) 0.626(4) 0.0295(11) 0.020(8) Uiso 1 1 d . . . . .
H22 H 0.237(4) 1.008(4) 0.1193(11) 0.015(8) Uiso 1 1 d . . . . .
H23 H 0.321(4) 1.243(4) 0.1407(11) 0.020(8) Uiso 1 1 d . . . . .
H25 H 0.725(3) 1.036(3) 0.1715(10) 0.009(7) Uiso 1 1 d . . . . .
H32 H -0.028(4) 0.518(4) 0.1286(13) 0.033(10) Uiso 1 1 d . . . . .
H33 H -0.089(4) 0.258(3) 0.1514(10) 0.014(7) Uiso 1 1 d . . . . .
H35 H 0.206(4) 0.264(4) 0.2500(12) 0.025(9) Uiso 1 1 d . . . . .
H111 H 0.407(4) 0.654(4) 0.1372(11) 0.021(8) Uiso 1 1 d . . . . .
H121 H 0.541(4) 0.729(4) 0.0651(11) 0.020(8) Uiso 1 1 d . . . . .
H122 H 0.381(3) 0.815(3) 0.0482(10) 0.011(7) Uiso 1 1 d . . . . .
H371 H 0.032(4) 0.758(4) 0.1584(12) 0.031(10) Uiso 1 1 d . . . . .
H372 H 0.188(3) 0.758(3) 0.1848(9) 0.005(6) Uiso 1 1 d . . . . .
O2 O 0.2308(2) 0.78428(19) 0.38561(6) 0.0152(4) Uani 1 1 d . . . . .
N21 N 0.4062(3) 0.9179(2) 0.44713(7) 0.0154(4) Uani 1 1 d . . . . .
N22 N 0.5811(3) 0.7700(3) 0.47384(8) 0.0177(4) Uani 1 1 d . . . . .
Cl21 Cl 0.25214(8) 1.28371(7) 0.34905(2) 0.02170(14) Uani 1 1 d . . . . .
Cl22 Cl -0.32871(10) 1.22331(10) 0.30828(3) 0.0375(2) Uani 1 1 d . . . . .
Cl23 Cl 0.38054(8) 0.96229(8) 0.26146(2) 0.02193(14) Uani 1 1 d . . . . .
Cl24 Cl 0.91604(8) 0.67384(8) 0.27545(3) 0.02604(16) Uani 1 1 d . . . . .
C41 C 0.2377(3) 0.9450(3) 0.38449(8) 0.0141(5) Uani 1 1 d . . . . .
C42 C 0.2582(3) 0.9733(3) 0.43335(9) 0.0161(5) Uani 1 1 d . . . . .
C43 C 0.5396(3) 1.0024(3) 0.44301(9) 0.0183(5) Uani 1 1 d . . . . .
C44 C 0.6487(3) 0.9095(3) 0.45993(9) 0.0186(5) Uani 1 1 d . . . . .
C45 C 0.4353(3) 0.7773(3) 0.46575(9) 0.0162(5) Uani 1 1 d . . . . .
C51 C 0.0941(3) 1.0192(3) 0.36781(8) 0.0151(5) Uani 1 1 d . . . . .
C52 C -0.0402(3) 0.9355(3) 0.36894(9) 0.0181(5) Uani 1 1 d . . . . .
C53 C -0.1713(3) 0.9989(3) 0.35193(10) 0.0214(5) Uani 1 1 d . . . . .
C54 C -0.1683(3) 1.1483(3) 0.33290(10) 0.0219(6) Uani 1 1 d . . . . .
C55 C -0.0399(3) 1.2377(3) 0.33224(10) 0.0209(5) Uani 1 1 d . . . . .
C56 C 0.0902(3) 1.1716(3) 0.35001(9) 0.0160(5) Uani 1 1 d . . . . .
C61 C 0.4221(3) 0.7263(3) 0.32630(8) 0.0143(5) Uani 1 1 d . . . . .
C62 C 0.5156(3) 0.6168(3) 0.34769(9) 0.0168(5) Uani 1 1 d . . . . .
C63 C 0.6674(3) 0.6005(3) 0.33270(9) 0.0182(5) Uani 1 1 d . . . . .
C64 C 0.7267(3) 0.6956(3) 0.29560(9) 0.0176(5) Uani 1 1 d . . . . .
C65 C 0.6406(3) 0.8085(3) 0.27373(9) 0.0164(5) Uani 1 1 d . . . . .
C66 C 0.4885(3) 0.8222(3) 0.28983(9) 0.0152(5) Uani 1 1 d . . . . .
C67 C 0.2554(3) 0.7302(3) 0.34195(9) 0.0158(5) Uani 1 1 d . . . . .
H20 H 0.616(5) 0.696(5) 0.4877(15) 0.051(13) Uiso 1 1 d . . . . .
H43 H 0.549(4) 1.100(4) 0.4322(12) 0.029(9) Uiso 1 1 d . . . . .
H44 H 0.758(4) 0.926(4) 0.4640(11) 0.024(9) Uiso 1 1 d . . . . .
H45 H 0.364(3) 0.697(3) 0.4725(10) 0.012(7) Uiso 1 1 d . . . . .
H52 H -0.039(4) 0.833(4) 0.3805(11) 0.021(8) Uiso 1 1 d . . . . .
H53 H -0.264(4) 0.944(3) 0.3519(10) 0.014(7) Uiso 1 1 d . . . . .
H55 H -0.044(4) 1.338(4) 0.3212(11) 0.017(8) Uiso 1 1 d . . . . .
H62 H 0.469(4) 0.556(3) 0.3735(11) 0.014(7) Uiso 1 1 d . . . . .
H63 H 0.721(4) 0.512(4) 0.3486(12) 0.032(10) Uiso 1 1 d . . . . .
H65 H 0.677(4) 0.873(4) 0.2503(12) 0.021(8) Uiso 1 1 d . . . . .
H411 H 0.331(3) 0.987(3) 0.3638(9) 0.003(6) Uiso 1 1 d . . . . .
H421 H 0.253(4) 1.084(4) 0.4365(10) 0.015(8) Uiso 1 1 d . . . . .
H422 H 0.182(4) 0.917(4) 0.4513(11) 0.017(8) Uiso 1 1 d . . . . .
H671 H 0.216(3) 0.632(4) 0.3453(10) 0.013(7) Uiso 1 1 d . . . . .
H672 H 0.200(4) 0.785(4) 0.3215(11) 0.014(7) Uiso 1 1 d . . . . .
O11 O 0.3052(2) -0.1468(2) -0.03707(7) 0.0202(4) Uani 1 1 d . . . . .
O12 O 0.1912(2) -0.3169(2) -0.07218(7) 0.0247(4) Uani 1 1 d . . . . .
O13 O 0.0626(2) 0.2771(2) -0.02383(7) 0.0206(4) Uani 1 1 d . . . . .
O14 O 0.2556(2) 0.1132(2) -0.02011(7) 0.0200(4) Uani 1 1 d . . . . .
C71 C 0.1937(3) -0.1914(3) -0.05920(8) 0.0164(5) Uani 1 1 d . . . . .
C72 C 0.0649(3) -0.0848(3) -0.06946(9) 0.0183(5) Uani 1 1 d . . . . .
C73 C 0.0366(3) 0.0564(3) -0.05919(9) 0.0173(5) Uani 1 1 d . . . . .
C74 C 0.1249(3) 0.1556(3) -0.03266(9) 0.0147(5) Uani 1 1 d . . . . .
H11 H 0.288(5) -0.038(5) -0.0313(16) 0.058(13) Uiso 1 1 d . . . . .
H72 H -0.016(5) -0.134(5) -0.0857(14) 0.045(12) Uiso 1 1 d . . . . .
H73 H -0.049(4) 0.102(4) -0.0684(12) 0.027(9) Uiso 1 1 d . . . . .
O21 O 1.1457(2) 0.7861(2) 0.53993(7) 0.0219(4) Uani 1 1 d . . . . .
O22 O 1.3212(2) 0.6534(3) 0.57655(8) 0.0291(5) Uani 1 1 d . . . . .
O23 O 0.7273(2) 0.5469(2) 0.52281(7) 0.0231(4) Uani 1 1 d . . . . .
O24 O 0.8886(2) 0.7407(2) 0.51874(7) 0.0219(4) Uani 1 1 d . . . . .
C81 C 1.1946(3) 0.6621(3) 0.56238(9) 0.0199(5) Uani 1 1 d . . . . .
C82 C 1.0922(3) 0.5253(3) 0.57087(10) 0.0206(5) Uani 1 1 d . . . . .
C83 C 0.9520(3) 0.5012(3) 0.55871(9) 0.0188(5) Uani 1 1 d . . . . .
C84 C 0.8492(3) 0.6039(3) 0.53158(9) 0.0169(5) Uani 1 1 d . . . . .
H21 H 1.044(6) 0.773(5) 0.5296(16) 0.058(14) Uiso 1 1 d . . . . .
H82 H 1.135(4) 0.436(4) 0.5853(12) 0.026(9) Uiso 1 1 d . . . . .
H83 H 0.911(4) 0.409(4) 0.5675(12) 0.031(10) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C11 1.422(3) . ?
O1 C37 1.436(3) . ?
N11 C15 1.339(3) . ?
N11 C13 1.384(3) . ?
N11 C12 1.462(3) . ?
N12 C15 1.325(3) . ?
N12 C14 1.380(3) . ?
N12 H10 0.88(4) . ?
Cl11 C26 1.747(2) . ?
Cl12 C24 1.735(3) . ?
Cl13 C36 1.739(2) . ?
Cl14 C34 1.744(3) . ?
C11 C21 1.522(3) . ?
C11 C12 1.526(3) . ?
C11 H111 0.99(3) . ?
C12 H121 1.00(3) . ?
C12 H122 1.03(3) . ?
C13 C14 1.354(4) . ?
C13 H13 1.01(4) . ?
C14 H14 0.89(3) . ?
C15 H15 0.88(3) . ?
C21 C26 1.393(3) . ?
C21 C22 1.395(3) . ?
C22 C23 1.390(4) . ?
C22 H22 0.97(3) . ?
C23 C24 1.384(4) . ?
C23 H23 0.97(3) . ?
C24 C25 1.392(4) . ?
C25 C26 1.388(3) . ?
C25 H25 0.95(3) . ?
C31 C36 1.394(4) . ?
C31 C32 1.398(3) . ?
C31 C37 1.506(3) . ?
C32 C33 1.390(4) . ?
C32 H32 0.95(4) . ?
C33 C34 1.388(4) . ?
C33 H33 0.97(3) . ?
C34 C35 1.384(4) . ?
C35 C36 1.386(4) . ?
C35 H35 0.92(4) . ?
C37 H371 0.98(4) . ?
C37 H372 0.97(3) . ?
O2 C41 1.423(3) . ?
O2 C67 1.434(3) . ?
N21 C45 1.338(3) . ?
N21 C43 1.387(3) . ?
N21 C42 1.461(3) . ?
N22 C45 1.324(3) . ?
N22 C44 1.383(3) . ?
N22 H20 0.81(5) . ?
Cl21 C56 1.739(3) . ?
Cl22 C54 1.735(3) . ?
Cl23 C66 1.742(3) . ?
Cl24 C64 1.744(3) . ?
C41 C51 1.514(4) . ?
C41 C42 1.526(3) . ?
C41 H411 1.04(3) . ?
C42 H421 1.00(3) . ?
C42 H422 0.93(3) . ?
C43 C44 1.351(4) . ?
C43 H43 0.89(4) . ?
C44 H44 1.00(3) . ?
C45 H45 0.95(3) . ?
C51 C52 1.395(4) . ?
C51 C56 1.396(3) . ?
C52 C53 1.387(4) . ?
C52 H52 0.94(3) . ?
C53 C54 1.381(4) . ?
C53 H53 0.95(3) . ?
C54 C55 1.381(4) . ?
C55 C56 1.397(4) . ?
C55 H55 0.92(3) . ?
C61 C66 1.395(4) . ?
C61 C62 1.399(4) . ?
C61 C67 1.506(4) . ?
C62 C63 1.388(4) . ?
C62 H62 0.95(3) . ?
C63 C64 1.382(4) . ?
C63 H63 1.00(4) . ?
C64 C65 1.386(4) . ?
C65 C66 1.396(4) . ?
C65 H65 0.89(3) . ?
C67 H671 0.93(3) . ?
C67 H672 0.91(3) . ?
O11 C71 1.309(3) . ?
O11 H11 1.00(5) . ?
O12 C71 1.218(3) . ?
O13 C74 1.250(3) . ?
O14 C74 1.278(3) . ?
C71 C72 1.499(3) . ?
C72 C73 1.338(4) . ?
C72 H72 1.02(4) . ?
C73 C74 1.502(4) . ?
C73 H73 0.90(4) . ?
O21 C81 1.309(3) . ?
O21 H21 0.98(5) . ?
O22 C81 1.220(3) . ?
O23 C84 1.246(3) . ?
O24 C84 1.272(3) . ?
C81 C82 1.502(4) . ?
C82 C83 1.338(4) . ?
C82 H82 0.95(4) . ?
C83 C84 1.496(4) . ?
C83 H83 0.90(4) . ?

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
C11 O1 C37 114.03(18) . . ?
C15 N11 C13 108.7(2) . . ?
C15 N11 C12 125.6(2) . . ?
C13 N11 C12 125.7(2) . . ?
C15 N12 C14 109.2(2) . . ?
C15 N12 H10 124(3) . . ?
C14 N12 H10 127(3) . . ?
O1 C11 C21 111.0(2) . . ?
O1 C11 C12 105.24(19) . . ?
C21 C11 C12 109.9(2) . . ?
O1 C11 H111 110.9(19) . . ?
C21 C11 H111 110.1(19) . . ?
C12 C11 H111 109.5(19) . . ?
N11 C12 C11 111.3(2) . . ?
N11 C12 H121 105.8(19) . . ?
C11 C12 H121 110.0(19) . . ?
N11 C12 H122 109.1(16) . . ?
C11 C12 H122 108.0(17) . . ?
H121 C12 H122 113(2) . . ?
C14 C13 N11 106.8(2) . . ?
C14 C13 H13 128(2) . . ?
N11 C13 H13 125(2) . . ?
C13 C14 N12 107.0(2) . . ?
C13 C14 H14 129(2) . . ?
N12 C14 H14 124(2) . . ?
N12 C15 N11 108.2(2) . . ?
N12 C15 H15 128(2) . . ?
N11 C15 H15 124(2) . . ?
C26 C21 C22 117.3(2) . . ?
C26 C21 C11 122.7(2) . . ?
C22 C21 C11 119.9(2) . . ?
C23 C22 C21 121.8(2) . . ?
C23 C22 H22 121.1(19) . . ?
C21 C22 H22 117.1(19) . . ?
C24 C23 C22 118.8(2) . . ?
C24 C23 H23 120.6(19) . . ?
C22 C23 H23 120.6(19) . . ?
C23 C24 C25 121.5(2) . . ?
C23 C24 Cl12 118.7(2) . . ?
C25 C24 Cl12 119.8(2) . . ?
C26 C25 C24 118.1(2) . . ?
C26 C25 H25 117.7(18) . . ?
C24 C25 H25 124.2(18) . . ?
C25 C26 C21 122.5(2) . . ?
C25 C26 Cl11 117.85(19) . . ?
C21 C26 Cl11 119.64(19) . . ?
C36 C31 C32 117.5(2) . . ?
C36 C31 C37 123.9(2) . . ?
C32 C31 C37 118.5(2) . . ?
C33 C32 C31 121.6(2) . . ?
C33 C32 H32 123(2) . . ?
C31 C32 H32 116(2) . . ?
C34 C33 C32 118.6(2) . . ?
C34 C33 H33 121.3(18) . . ?
C32 C33 H33 119.9(18) . . ?
C35 C34 C33 121.5(2) . . ?
C35 C34 Cl14 119.2(2) . . ?
C33 C34 Cl14 119.3(2) . . ?
C34 C35 C36 118.5(2) . . ?
C34 C35 H35 121(2) . . ?
C36 C35 H35 121(2) . . ?
C35 C36 C31 122.1(2) . . ?
C35 C36 Cl13 117.42(19) . . ?
C31 C36 Cl13 120.46(19) . . ?
O1 C37 C31 111.6(2) . . ?
O1 C37 H371 103(2) . . ?
C31 C37 H371 109(2) . . ?
O1 C37 H372 111.0(16) . . ?
C31 C37 H372 109.6(16) . . ?
H371 C37 H372 113(3) . . ?
C41 O2 C67 114.16(19) . . ?
C45 N21 C43 108.8(2) . . ?
C45 N21 C42 125.6(2) . . ?
C43 N21 C42 125.6(2) . . ?
C45 N22 C44 109.1(2) . . ?
C45 N22 H20 122(3) . . ?
C44 N22 H20 129(3) . . ?
O2 C41 C51 111.4(2) . . ?
O2 C41 C42 104.85(19) . . ?
C51 C41 C42 111.3(2) . . ?
O2 C41 H411 110.2(15) . . ?
C51 C41 H411 109.5(15) . . ?
C42 C41 H411 109.4(15) . . ?
N21 C42 C41 110.8(2) . . ?
N21 C42 H421 107.9(18) . . ?
C41 C42 H421 110.4(18) . . ?
N21 C42 H422 109(2) . . ?
C41 C42 H422 106(2) . . ?
H421 C42 H422 113(3) . . ?
C44 C43 N21 106.7(2) . . ?
C44 C43 H43 127(2) . . ?
N21 C43 H43 126(2) . . ?
C43 C44 N22 107.2(2) . . ?
C43 C44 H44 132(2) . . ?
N22 C44 H44 120(2) . . ?
N22 C45 N21 108.3(2) . . ?
N22 C45 H45 125.8(18) . . ?
N21 C45 H45 125.9(18) . . ?
C52 C51 C56 117.3(2) . . ?
C52 C51 C41 120.6(2) . . ?
C56 C51 C41 122.1(2) . . ?
C53 C52 C51 121.8(3) . . ?
C53 C52 H52 120(2) . . ?
C51 C52 H52 118(2) . . ?
C54 C53 C52 119.1(3) . . ?
C54 C53 H53 117.5(19) . . ?
C52 C53 H53 123.4(19) . . ?
C53 C54 C55 121.5(3) . . ?
C53 C54 Cl22 118.9(2) . . ?
C55 C54 Cl22 119.6(2) . . ?
C54 C55 C56 118.3(3) . . ?
C54 C55 H55 119(2) . . ?
C56 C55 H55 123(2) . . ?
C51 C56 C55 122.0(2) . . ?
C51 C56 Cl21 119.6(2) . . ?
C55 C56 Cl21 118.4(2) . . ?
C66 C61 C62 117.4(2) . . ?
C66 C61 C67 123.4(2) . . ?
C62 C61 C67 119.1(2) . . ?
C63 C62 C61 121.8(2) . . ?
C63 C62 H62 122.4(19) . . ?
C61 C62 H62 115.8(19) . . ?
C64 C63 C62 118.6(2) . . ?
C64 C63 H63 126(2) . . ?
C62 C63 H63 115(2) . . ?
C63 C64 C65 122.1(2) . . ?
C63 C64 Cl24 119.3(2) . . ?
C65 C64 Cl24 118.6(2) . . ?
C64 C65 C66 117.7(2) . . ?
C64 C65 H65 124(2) . . ?
C66 C65 H65 119(2) . . ?
C61 C66 C65 122.3(2) . . ?
C61 C66 Cl23 120.4(2) . . ?
C65 C66 Cl23 117.3(2) . . ?
O2 C67 C61 112.1(2) . . ?
O2 C67 H671 106.1(19) . . ?
C61 C67 H671 109.6(19) . . ?
O2 C67 H672 110(2) . . ?
C61 C67 H672 112(2) . . ?
H671 C67 H672 106(3) . . ?
C71 O11 H11 109(3) . . ?
C74 O14 H11 110.1(18) . . ?
O12 C71 O11 122.2(2) . . ?
O12 C71 C72 118.4(2) . . ?
O11 C71 C72 119.4(2) . . ?
C73 C72 C71 131.5(2) . . ?
C73 C72 H72 116(2) . . ?
C71 C72 H72 112(2) . . ?
C72 C73 C74 130.1(2) . . ?
C72 C73 H73 118(2) . . ?
C74 C73 H73 112(2) . . ?
O13 C74 O14 123.7(2) . . ?
O13 C74 C73 116.3(2) . . ?
O14 C74 C73 119.9(2) . . ?
C81 O21 H21 112(3) . . ?
C84 O24 H21 112.2(18) . . ?
O22 C81 O21 122.3(3) . . ?
O22 C81 C82 118.6(3) . . ?
O21 C81 C82 119.1(2) . . ?
C83 C82 C81 131.6(3) . . ?
C83 C82 H82 112(2) . . ?
C81 C82 H82 116(2) . . ?
C82 C83 C84 130.2(2) . . ?
C82 C83 H83 117(2) . . ?
C84 C83 H83 113(2) . . ?
O23 C84 O24 123.9(3) . . ?
O23 C84 C83 116.1(2) . . ?
O24 C84 C83 120.0(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
C37 O1 C11 C21 -77.1(2) . . . . ?
C37 O1 C11 C12 163.96(19) . . . . ?
C15 N11 C12 C11 89.4(3) . . . . ?
C13 N11 C12 C11 -92.8(3) . . . . ?
O1 C11 C12 N11 -64.5(3) . . . . ?
C21 C11 C12 N11 175.9(2) . . . . ?
C15 N11 C13 C14 0.2(3) . . . . ?
C12 N11 C13 C14 -177.9(2) . . . . ?
N11 C13 C14 N12 -0.1(3) . . . . ?
C15 N12 C14 C13 0.0(3) . . . . ?
C14 N12 C15 N11 0.1(3) . . . . ?
C13 N11 C15 N12 -0.2(3) . . . . ?
C12 N11 C15 N12 177.9(2) . . . . ?
O1 C11 C21 C26 160.6(2) . . . . ?
C12 C11 C21 C26 -83.4(3) . . . . ?
O1 C11 C21 C22 -20.5(3) . . . . ?
C12 C11 C21 C22 95.6(3) . . . . ?
C26 C21 C22 C23 -1.2(4) . . . . ?
C11 C21 C22 C23 179.8(2) . . . . ?
C21 C22 C23 C24 0.2(4) . . . . ?
C22 C23 C24 C25 1.0(4) . . . . ?
C22 C23 C24 Cl12 -177.15(19) . . . . ?
C23 C24 C25 C26 -1.2(4) . . . . ?
Cl12 C24 C25 C26 176.93(19) . . . . ?
C24 C25 C26 C21 0.2(4) . . . . ?
C24 C25 C26 Cl11 -179.04(19) . . . . ?
C22 C21 C26 C25 1.0(4) . . . . ?
C11 C21 C26 C25 180.0(2) . . . . ?
C22 C21 C26 Cl11 -179.78(18) . . . . ?
C11 C21 C26 Cl11 -0.8(3) . . . . ?
C36 C31 C32 C33 2.7(4) . . . . ?
C37 C31 C32 C33 -175.5(2) . . . . ?
C31 C32 C33 C34 -0.2(4) . . . . ?
C32 C33 C34 C35 -2.6(4) . . . . ?
C32 C33 C34 Cl14 178.1(2) . . . . ?
C33 C34 C35 C36 2.7(4) . . . . ?
Cl14 C34 C35 C36 -178.03(19) . . . . ?
C34 C35 C36 C31 0.0(4) . . . . ?
C34 C35 C36 Cl13 179.24(19) . . . . ?
C32 C31 C36 C35 -2.7(4) . . . . ?
C37 C31 C36 C35 175.5(2) . . . . ?
C32 C31 C36 Cl13 178.13(19) . . . . ?
C37 C31 C36 Cl13 -3.7(3) . . . . ?
C11 O1 C37 C31 -86.4(2) . . . . ?
C36 C31 C37 O1 114.4(3) . . . . ?
C32 C31 C37 O1 -67.4(3) . . . . ?
C67 O2 C41 C51 76.4(3) . . . . ?
C67 O2 C41 C42 -163.0(2) . . . . ?
C45 N21 C42 C41 -88.7(3) . . . . ?
C43 N21 C42 C41 91.2(3) . . . . ?
O2 C41 C42 N21 66.5(3) . . . . ?
C51 C41 C42 N21 -172.8(2) . . . . ?
C45 N21 C43 C44 -0.5(3) . . . . ?
C42 N21 C43 C44 179.6(2) . . . . ?
N21 C43 C44 N22 0.4(3) . . . . ?
C45 N22 C44 C43 -0.1(3) . . . . ?
C44 N22 C45 N21 -0.2(3) . . . . ?
C43 N21 C45 N22 0.5(3) . . . . ?
C42 N21 C45 N22 -179.6(2) . . . . ?
O2 C41 C51 C52 19.6(3) . . . . ?
C42 C41 C51 C52 -97.0(3) . . . . ?
O2 C41 C51 C56 -159.1(2) . . . . ?
C42 C41 C51 C56 84.2(3) . . . . ?
C56 C51 C52 C53 1.8(4) . . . . ?
C41 C51 C52 C53 -176.9(2) . . . . ?
C51 C52 C53 C54 0.8(4) . . . . ?
C52 C53 C54 C55 -2.9(4) . . . . ?
C52 C53 C54 Cl22 175.8(2) . . . . ?
C53 C54 C55 C56 2.2(4) . . . . ?
Cl22 C54 C55 C56 -176.4(2) . . . . ?
C52 C51 C56 C55 -2.5(4) . . . . ?
C41 C51 C56 C55 176.2(2) . . . . ?
C52 C51 C56 Cl21 178.25(19) . . . . ?
C41 C51 C56 Cl21 -3.0(3) . . . . ?
C54 C55 C56 C51 0.6(4) . . . . ?
C54 C55 C56 Cl21 179.8(2) . . . . ?
C66 C61 C62 C63 -1.8(4) . . . . ?
C67 C61 C62 C63 175.3(2) . . . . ?
C61 C62 C63 C64 0.0(4) . . . . ?
C62 C63 C64 C65 1.5(4) . . . . ?
C62 C63 C64 Cl24 -178.5(2) . . . . ?
C63 C64 C65 C66 -1.2(4) . . . . ?
Cl24 C64 C65 C66 178.81(19) . . . . ?
C62 C61 C66 C65 2.1(4) . . . . ?
C67 C61 C66 C65 -174.8(2) . . . . ?
C62 C61 C66 Cl23 -179.68(19) . . . . ?
C67 C61 C66 Cl23 3.4(3) . . . . ?
C64 C65 C66 C61 -0.7(4) . . . . ?
C64 C65 C66 Cl23 -178.9(2) . . . . ?
C41 O2 C67 C61 79.9(3) . . . . ?
C66 C61 C67 O2 -111.7(3) . . . . ?
C62 C61 C67 O2 71.4(3) . . . . ?
O12 C71 C72 C73 179.0(3) . . . . ?
O11 C71 C72 C73 -1.5(5) . . . . ?
C71 C72 C73 C74 -1.4(5) . . . . ?
C72 C73 C74 O13 -172.1(3) . . . . ?
C72 C73 C74 O14 7.4(4) . . . . ?
O22 C81 C82 C83 -178.3(3) . . . . ?
O21 C81 C82 C83 1.4(5) . . . . ?
C81 C82 C83 C84 0.8(5) . . . . ?
C82 C83 C84 O23 175.3(3) . . . . ?
C82 C83 C84 O24 -4.5(5) . . . . ?

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
N12 H10 O13 0.88(4) 1.84(4) 2.709(3) 170(4) .
N22 H20 O23 0.81(5) 1.91(5) 2.703(3) 170(5) .
O11 H11 O14 1.00(5) 1.44(5) 2.443(3) 176(5) .
O21 H21 O24 0.98(5) 1.47(5) 2.443(3) 174(5) .

_refine_diff_density_max         0.643
_refine_diff_density_min         -0.354
_refine_diff_density_rms         0.086

####################################################################### 
# 
# 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_a_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 2043354'
loop_
_audit_author_name
_audit_author_address
'Andrei Churakov'
;Institute of General and Inorganic Chemistry RAS
Russia
;
_audit_update_record             
;
2020-11-09 deposited with the CCDC.	2021-05-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C18 H14 Cl4 N2 O), C4 H4 O4'
_chemical_formula_sum            'C40 H32 Cl8 N4 O6'
_chemical_formula_weight         948.29

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   8.1544(2)
_cell_length_b                   8.9059(2)
_cell_length_c                   14.8899(4)
_cell_angle_alpha                81.5113(8)
_cell_angle_beta                 81.5921(8)
_cell_angle_gamma                70.0821(7)
_cell_volume                     1000.15(4)
_cell_formula_units_Z            1
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    9945
_cell_measurement_theta_min      2.496
_cell_measurement_theta_max      30.508

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.574
_exptl_crystal_F_000             484
_exptl_transmission_factor_min   0.8206
_exptl_transmission_factor_max   0.8622
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.350
_exptl_crystal_size_min          0.350
_exptl_absorpt_coefficient_mu    0.618
_shelx_estimated_absorpt_T_min   0.790
_shelx_estimated_absorpt_T_max   0.813
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   'SADABS (Bruker, 2016)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker SMART APEX II'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16843
_diffrn_reflns_av_unetI/netI     0.0199
_diffrn_reflns_av_R_equivalents  0.0198
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.446
_diffrn_reflns_theta_max         27.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             4814
_reflns_number_gt                4526
_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       'APEX3 (Bruker, 2018)'
_computing_cell_refinement       'SAINT (Bruker, 2018)'
_computing_data_reduction        'SAINT (Bruker, 2018)'
_computing_structure_solution    'SHELXT (Sheldrick, 2016)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0263P)²+0.5113P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     difmap
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4814
_refine_ls_number_parameters     326
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0282
_refine_ls_R_factor_gt           0.0262
_refine_ls_wR_factor_ref         0.0639
_refine_ls_wR_factor_gt          0.0629
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_restrained_S_all      1.065
_refine_ls_shift/su_max          0.001
_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
O1 O 0.69568(11) 0.25194(10) 0.73158(6) 0.01260(17) Uani 1 1 d . . . . .
N1 N 0.56351(13) 0.45564(12) 0.88827(7) 0.01157(19) Uani 1 1 d . . . . .
N2 N 0.71066(14) 0.60497(13) 0.91962(7) 0.0142(2) Uani 1 1 d . . . . .
Cl1 Cl 0.12142(4) 0.45136(3) 0.80805(2) 0.01656(7) Uani 1 1 d . . . . .
Cl2 Cl 0.09123(4) -0.10536(4) 0.72467(2) 0.01958(8) Uani 1 1 d . . . . .
Cl3 Cl 0.71971(4) 0.39522(4) 0.43210(2) 0.01813(7) Uani 1 1 d . . . . .
Cl4 Cl 0.82654(5) 0.92374(4) 0.50877(2) 0.02256(8) Uani 1 1 d . . . . .
C11 C 0.51761(15) 0.31190(14) 0.76948(8) 0.0111(2) Uani 1 1 d . . . . .
C12 C 0.52213(16) 0.31528(14) 0.87161(8) 0.0125(2) Uani 1 1 d . . . . .
C13 C 0.45406(16) 0.61296(15) 0.87898(8) 0.0147(2) Uani 1 1 d . . . . .
C14 C 0.54617(17) 0.70364(15) 0.89869(8) 0.0153(2) Uani 1 1 d . . . . .
C15 C 0.71581(16) 0.45735(15) 0.91253(8) 0.0131(2) Uani 1 1 d . . . . .
C21 C 0.41152(15) 0.20824(14) 0.75493(8) 0.0112(2) Uani 1 1 d . . . . .
C22 C 0.49142(16) 0.05620(14) 0.72510(8) 0.0139(2) Uani 1 1 d . . . . .
C23 C 0.39377(17) -0.03951(15) 0.71365(8) 0.0154(2) Uani 1 1 d . . . . .
C24 C 0.21347(16) 0.01675(15) 0.73423(8) 0.0140(2) Uani 1 1 d . . . . .
C25 C 0.12780(16) 0.16768(15) 0.76331(8) 0.0136(2) Uani 1 1 d . . . . .
C26 C 0.22885(15) 0.26139(14) 0.77243(8) 0.0123(2) Uani 1 1 d . . . . .
C31 C 0.74632(15) 0.44423(14) 0.60421(8) 0.0123(2) Uani 1 1 d . . . . .
C32 C 0.77513(16) 0.53465(15) 0.66551(8) 0.0135(2) Uani 1 1 d . . . . .
C33 C 0.80213(16) 0.68113(15) 0.63698(9) 0.0150(2) Uani 1 1 d . . . . .
C34 C 0.79730(16) 0.73924(15) 0.54563(9) 0.0152(2) Uani 1 1 d . . . . .
C35 C 0.77075(16) 0.65275(15) 0.48188(9) 0.0159(2) Uani 1 1 d . . . . .
C36 C 0.74727(15) 0.50615(15) 0.51243(8) 0.0137(2) Uani 1 1 d . . . . .
C37 C 0.72041(16) 0.28340(15) 0.63466(8) 0.0140(2) Uani 1 1 d . . . . .
H10 H 0.4606(18) 0.4229(17) 0.7409(9) 0.007(3) Uiso 1 1 d . . . . .
H13 H 0.339(2) 0.6393(19) 0.8629(11) 0.021(4) Uiso 1 1 d . . . . .
H14 H 0.509(2) 0.8150(19) 0.8998(10) 0.017(4) Uiso 1 1 d . . . . .
H15 H 0.812(2) 0.3621(19) 0.9243(10) 0.015(4) Uiso 1 1 d . . . . .
H22 H 0.614(2) 0.0168(19) 0.7125(11) 0.021(4) Uiso 1 1 d . . . . .
H23 H 0.447(2) -0.141(2) 0.6919(11) 0.021(4) Uiso 1 1 d . . . . .
H25 H 0.004(2) 0.2054(19) 0.7764(11) 0.018(4) Uiso 1 1 d . . . . .
H32 H 0.7788(19) 0.4952(18) 0.7264(11) 0.013(4) Uiso 1 1 d . . . . .
H33 H 0.824(2) 0.7369(19) 0.6803(11) 0.020(4) Uiso 1 1 d . . . . .
H35 H 0.766(2) 0.691(2) 0.4207(12) 0.027(4) Uiso 1 1 d . . . . .
H121 H 0.612(2) 0.2176(18) 0.8956(10) 0.013(4) Uiso 1 1 d . . . . .
H122 H 0.4103(19) 0.3207(17) 0.9047(10) 0.010(3) Uiso 1 1 d . . . . .
H371 H 0.624(2) 0.2774(18) 0.6072(10) 0.014(4) Uiso 1 1 d . . . . .
H372 H 0.826(2) 0.1954(19) 0.6146(11) 0.020(4) Uiso 1 1 d . . . . .
O11 O 0.95369(12) 0.71412(11) 0.94712(7) 0.01848(19) Uani 1 1 d . . . . .
O12 O 0.72854(13) 0.93405(13) 0.97964(10) 0.0371(3) Uani 1 1 d . . . . .
C16 C 0.88414(17) 0.86230(15) 0.96839(9) 0.0164(2) Uani 1 1 d . . . . .
C17 C 1.02004(16) 0.93473(15) 0.97884(9) 0.0154(2) Uani 1 1 d . . . . .
H11 H 0.868(3) 0.672(3) 0.9397(16) 0.063(7) Uiso 1 1 d . . . . .
H17 H 1.135(2) 0.886(2) 0.9542(11) 0.023(4) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C11 1.4259(13) . ?
O1 C37 1.4268(14) . ?
N1 C15 1.3487(15) . ?
N1 C13 1.3804(16) . ?
N1 C12 1.4634(15) . ?
N2 C15 1.3203(16) . ?
N2 C14 1.3809(16) . ?
Cl1 C26 1.7408(12) . ?
Cl2 C24 1.7385(12) . ?
Cl3 C36 1.7424(12) . ?
Cl4 C34 1.7380(12) . ?
C11 C21 1.5184(16) . ?
C11 C12 1.5315(16) . ?
C11 H10 0.998(14) . ?
C12 H121 0.984(15) . ?
C12 H122 0.960(15) . ?
C13 C14 1.3602(17) . ?
C13 H13 0.948(17) . ?
C14 H14 0.935(16) . ?
C15 H15 0.952(16) . ?
C21 C22 1.3953(16) . ?
C21 C26 1.3976(16) . ?
C22 C23 1.3910(17) . ?
C22 H22 0.938(17) . ?
C23 C24 1.3850(17) . ?
C23 H23 0.940(17) . ?
C24 C25 1.3877(17) . ?
C25 C26 1.3888(16) . ?
C25 H25 0.947(16) . ?
C31 C32 1.3948(16) . ?
C31 C36 1.3961(17) . ?
C31 C37 1.5126(16) . ?
C32 C33 1.3912(17) . ?
C32 H32 0.923(15) . ?
C33 C34 1.3833(18) . ?
C33 H33 0.939(16) . ?
C34 C35 1.3896(17) . ?
C35 C36 1.3848(17) . ?
C35 H35 0.926(17) . ?
C37 H371 0.958(16) . ?
C37 H372 0.991(16) . ?
O11 C16 1.3132(15) . ?
O11 H11 0.93(3) . ?
O12 C16 1.2097(16) . ?
C16 C17 1.4952(17) . ?
C17 C17 1.324(2) 2_777 ?
C17 H17 0.932(17) . ?

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
C11 O1 C37 113.98(9) . . ?
C15 N1 C13 107.08(10) . . ?
C15 N1 C12 127.03(10) . . ?
C13 N1 C12 125.86(10) . . ?
C15 N2 C14 105.91(10) . . ?
O1 C11 C21 112.28(9) . . ?
O1 C11 C12 106.36(9) . . ?
C21 C11 C12 110.42(9) . . ?
O1 C11 H10 110.1(8) . . ?
C21 C11 H10 108.0(8) . . ?
C12 C11 H10 109.6(8) . . ?
N1 C12 C11 111.03(10) . . ?
N1 C12 H121 108.8(9) . . ?
C11 C12 H121 109.8(9) . . ?
N1 C12 H122 107.6(9) . . ?
C11 C12 H122 110.8(9) . . ?
H121 C12 H122 108.8(12) . . ?
C14 C13 N1 106.21(11) . . ?
C14 C13 H13 132.6(10) . . ?
N1 C13 H13 121.2(10) . . ?
C13 C14 N2 109.41(11) . . ?
C13 C14 H14 128.1(10) . . ?
N2 C14 H14 122.5(10) . . ?
N2 C15 N1 111.38(11) . . ?
N2 C15 H15 125.8(9) . . ?
N1 C15 H15 122.8(9) . . ?
C22 C21 C26 117.37(11) . . ?
C22 C21 C11 121.79(10) . . ?
C26 C21 C11 120.84(10) . . ?
C23 C22 C21 121.52(11) . . ?
C23 C22 H22 118.8(10) . . ?
C21 C22 H22 119.7(10) . . ?
C24 C23 C22 118.94(11) . . ?
C24 C23 H23 119.5(10) . . ?
C22 C23 H23 121.5(10) . . ?
C23 C24 C25 121.67(11) . . ?
C23 C24 Cl2 119.29(9) . . ?
C25 C24 Cl2 119.04(9) . . ?
C24 C25 C26 117.92(11) . . ?
C24 C25 H25 120.9(10) . . ?
C26 C25 H25 121.2(10) . . ?
C25 C26 C21 122.55(11) . . ?
C25 C26 Cl1 117.97(9) . . ?
C21 C26 Cl1 119.48(9) . . ?
C32 C31 C36 117.17(11) . . ?
C32 C31 C37 121.86(11) . . ?
C36 C31 C37 120.95(11) . . ?
C33 C32 C31 121.69(11) . . ?
C33 C32 H32 119.2(9) . . ?
C31 C32 H32 119.1(9) . . ?
C34 C33 C32 118.89(11) . . ?
C34 C33 H33 122.2(10) . . ?
C32 C33 H33 118.9(10) . . ?
C33 C34 C35 121.48(11) . . ?
C33 C34 Cl4 119.71(10) . . ?
C35 C34 Cl4 118.80(10) . . ?
C36 C35 C34 118.06(11) . . ?
C36 C35 H35 119.8(10) . . ?
C34 C35 H35 122.2(10) . . ?
C35 C36 C31 122.66(11) . . ?
C35 C36 Cl3 118.09(9) . . ?
C31 C36 Cl3 119.25(9) . . ?
O1 C37 C31 112.76(10) . . ?
O1 C37 H371 110.9(9) . . ?
C31 C37 H371 109.7(9) . . ?
O1 C37 H372 105.5(9) . . ?
C31 C37 H372 110.2(9) . . ?
H371 C37 H372 107.7(13) . . ?
C16 O11 H11 110.9(15) . . ?
O12 C16 O11 125.04(12) . . ?
O12 C16 C17 122.67(12) . . ?
O11 C16 C17 112.28(11) . . ?
C17 C17 C16 121.50(15) 2_777 . ?
C17 C17 H17 120.4(10) 2_777 . ?
C16 C17 H17 118.1(10) . . ?

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
C37 O1 C11 C21 76.39(12) . . . . ?
C37 O1 C11 C12 -162.74(9) . . . . ?
C15 N1 C12 C11 -106.82(13) . . . . ?
C13 N1 C12 C11 70.93(14) . . . . ?
O1 C11 C12 N1 79.16(11) . . . . ?
C21 C11 C12 N1 -158.78(10) . . . . ?
C15 N1 C13 C14 -0.26(13) . . . . ?
C12 N1 C13 C14 -178.37(11) . . . . ?
N1 C13 C14 N2 0.22(14) . . . . ?
C15 N2 C14 C13 -0.10(14) . . . . ?
C14 N2 C15 N1 -0.07(13) . . . . ?
C13 N1 C15 N2 0.21(14) . . . . ?
C12 N1 C15 N2 178.29(10) . . . . ?
O1 C11 C21 C22 12.37(15) . . . . ?
C12 C11 C21 C22 -106.14(12) . . . . ?
O1 C11 C21 C26 -168.59(10) . . . . ?
C12 C11 C21 C26 72.90(14) . . . . ?
C26 C21 C22 C23 -0.37(18) . . . . ?
C11 C21 C22 C23 178.70(11) . . . . ?
C21 C22 C23 C24 -1.34(18) . . . . ?
C22 C23 C24 C25 1.93(19) . . . . ?
C22 C23 C24 Cl2 -177.36(9) . . . . ?
C23 C24 C25 C26 -0.77(18) . . . . ?
Cl2 C24 C25 C26 178.52(9) . . . . ?
C24 C25 C26 C21 -1.04(18) . . . . ?
C24 C25 C26 Cl1 179.51(9) . . . . ?
C22 C21 C26 C25 1.59(17) . . . . ?
C11 C21 C26 C25 -177.49(11) . . . . ?
C22 C21 C26 Cl1 -178.97(9) . . . . ?
C11 C21 C26 Cl1 1.95(15) . . . . ?
C36 C31 C32 C33 0.59(18) . . . . ?
C37 C31 C32 C33 178.79(11) . . . . ?
C31 C32 C33 C34 1.06(18) . . . . ?
C32 C33 C34 C35 -1.69(19) . . . . ?
C32 C33 C34 Cl4 178.79(9) . . . . ?
C33 C34 C35 C36 0.63(19) . . . . ?
Cl4 C34 C35 C36 -179.85(9) . . . . ?
C34 C35 C36 C31 1.13(19) . . . . ?
C34 C35 C36 Cl3 -178.35(9) . . . . ?
C32 C31 C36 C35 -1.71(18) . . . . ?
C37 C31 C36 C35 -179.94(11) . . . . ?
C32 C31 C36 Cl3 177.76(9) . . . . ?
C37 C31 C36 Cl3 -0.46(16) . . . . ?
C11 O1 C37 C31 87.83(12) . . . . ?
C32 C31 C37 O1 11.17(16) . . . . ?
C36 C31 C37 O1 -170.70(10) . . . . ?
O12 C16 C17 C17 16.1(2) . . . 2_777 ?
O11 C16 C17 C17 -163.17(16) . . . 2_777 ?

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
O11 H11 N2 0.93(3) 1.67(3) 2.5898(14) 176(2) .

_refine_diff_density_max         0.397
_refine_diff_density_min         -0.225
_refine_diff_density_rms         0.048

####################################################################### 
# 
# 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_a_sq
_database_code_depnum_ccdc_archive 'CCDC 2043356'
loop_
_audit_author_name
_audit_author_address
'Andrei Churakov'
;Institute of General and Inorganic Chemistry RAS
Russia
;
_audit_update_record             
;
2020-11-09 deposited with the CCDC.	2021-05-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C18 H14 Cl4 N2 O), C6 H10 O4'
_chemical_formula_sum            'C42 H38 Cl8 N4 O6'
_chemical_formula_weight         978.36

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   12.6233(9)
_cell_length_b                   13.3497(9)
_cell_length_c                   16.0081(11)
_cell_angle_alpha                103.462(3)
_cell_angle_beta                 100.435(3)
_cell_angle_gamma                113.091(2)
_cell_volume                     2298.7(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    8048
_cell_measurement_theta_min      2.349
_cell_measurement_theta_max      30.068

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.413
_exptl_crystal_F_000             1004
_exptl_transmission_factor_min   0.8116
_exptl_transmission_factor_max   0.8622
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.540
_shelx_estimated_absorpt_T_min   0.900
_shelx_estimated_absorpt_T_max   0.948
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   'SADABS (Bruker, 2016)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            33109
_diffrn_reflns_av_unetI/netI     0.0634
_diffrn_reflns_av_R_equivalents  0.0489
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.373
_diffrn_reflns_theta_max         28.000
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             11091
_reflns_number_gt                7257
_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.
 
 Structure factors included contributions from the .fab file.
 
 _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, 2018)'
_computing_cell_refinement       'SAINT (Bruker, 2018)'
_computing_data_reduction        'SAINT (Bruker, 2018)'
_computing_structure_solution    'SHELXT (Sheldrick, 2016)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0445P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         11091
_refine_ls_number_parameters     549
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0784
_refine_ls_R_factor_gt           0.0427
_refine_ls_wR_factor_ref         0.1110
_refine_ls_wR_factor_gt          0.0993
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_restrained_S_all      1.057
_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
Cl11 Cl 0.13295(6) -0.44192(5) 0.35044(4) 0.03996(16) Uani 1 1 d . . . . .
Cl12 Cl 0.15484(6) -0.57719(5) 0.63972(4) 0.03619(15) Uani 1 1 d . . . . .
Cl13 Cl -0.17746(5) -0.18592(4) 0.54687(4) 0.03102(14) Uani 1 1 d . . . . .
Cl14 Cl 0.02297(5) 0.24998(5) 0.77397(4) 0.03443(15) Uani 1 1 d . . . . .
N11 N 0.35821(14) -0.07232(14) 0.42050(11) 0.0216(4) Uani 1 1 d . . . . .
N12 N 0.38412(15) 0.07197(15) 0.36909(12) 0.0252(4) Uani 1 1 d . . . . .
O1 O 0.19221(12) -0.10738(11) 0.53498(9) 0.0219(3) Uani 1 1 d . . . . .
C11 C 0.20771(17) -0.19833(16) 0.48050(13) 0.0204(4) Uani 1 1 d . . . . .
H11 H 0.150826 -0.229700 0.418034 0.024 Uiso 1 1 calc R U . . .
C12 C 0.33768(17) -0.14385(17) 0.47856(13) 0.0227(5) Uani 1 1 d . . . . .
H12A H 0.391317 -0.095510 0.540760 0.027 Uiso 1 1 calc R U . . .
H12B H 0.360503 -0.206080 0.457408 0.027 Uiso 1 1 calc R U . . .
C13 C 0.3743(2) -0.10321(19) 0.33757(14) 0.0296(5) Uani 1 1 d . . . . .
H13 H 0.373947 -0.173734 0.307602 0.036 Uiso 1 1 calc R U . . .
C14 C 0.39066(19) -0.01374(18) 0.30672(14) 0.0296(5) Uani 1 1 d . . . . .
H14 H 0.404492 -0.010714 0.250763 0.036 Uiso 1 1 calc R U . . .
C15 C 0.36511(17) 0.03416(18) 0.43675(14) 0.0242(5) Uani 1 1 d . . . . .
H15 H 0.357312 0.076369 0.489932 0.029 Uiso 1 1 calc R U . . .
C21 C 0.18929(17) -0.29524(16) 0.51928(13) 0.0190(4) Uani 1 1 d . . . . .
C22 C 0.15846(18) -0.40713(17) 0.46610(13) 0.0234(5) Uani 1 1 d . . . . .
C23 C 0.14814(18) -0.49441(17) 0.50203(13) 0.0254(5) Uani 1 1 d . . . . .
H23 H 0.127626 -0.569940 0.464394 0.031 Uiso 1 1 calc R U . . .
C24 C 0.16837(19) -0.46872(17) 0.59350(14) 0.0248(5) Uani 1 1 d . . . . .
C25 C 0.19821(19) -0.35911(18) 0.64896(14) 0.0287(5) Uani 1 1 d . . . . .
H25 H 0.211261 -0.342785 0.712009 0.034 Uiso 1 1 calc R U . . .
C26 C 0.20879(18) -0.27344(17) 0.61131(13) 0.0245(5) Uani 1 1 d . . . . .
H26 H 0.229903 -0.197950 0.649368 0.029 Uiso 1 1 calc R U . . .
C31 C 0.06147(17) -0.04115(17) 0.59342(13) 0.0205(4) Uani 1 1 d . . . . .
C32 C 0.16152(19) 0.06483(17) 0.64153(14) 0.0258(5) Uani 1 1 d . . . . .
H32 H 0.238494 0.076294 0.635365 0.031 Uiso 1 1 calc R U . . .
C33 C 0.15156(19) 0.15448(18) 0.69845(14) 0.0278(5) Uani 1 1 d . . . . .
H33 H 0.220821 0.226458 0.731103 0.033 Uiso 1 1 calc R U . . .
C34 C 0.03967(19) 0.13720(17) 0.70671(13) 0.0236(5) Uani 1 1 d . . . . .
C35 C -0.06212(19) 0.03292(17) 0.66151(13) 0.0242(5) Uani 1 1 d . . . . .
H35 H -0.138592 0.021500 0.668806 0.029 Uiso 1 1 calc R U . . .
C36 C -0.04913(18) -0.05458(17) 0.60512(13) 0.0221(4) Uani 1 1 d . . . . .
C37 C 0.06871(17) -0.13871(16) 0.53011(13) 0.0214(4) Uani 1 1 d . . . . .
H37A H 0.034410 -0.209120 0.546698 0.026 Uiso 1 1 calc R U . . .
H37B H 0.021188 -0.155590 0.467729 0.026 Uiso 1 1 calc R U . . .
Cl21 Cl 0.85718(5) 1.43893(4) 0.14680(3) 0.02791(13) Uani 1 1 d . . . . .
Cl22 Cl 0.85501(5) 1.58319(4) -0.13931(3) 0.02874(13) Uani 1 1 d . . . . .
Cl23 Cl 1.19240(4) 1.19600(4) -0.03585(4) 0.03076(14) Uani 1 1 d . . . . .
Cl24 Cl 1.00570(5) 0.76335(4) -0.26793(3) 0.02972(13) Uani 1 1 d . . . . .
N21 N 0.64413(14) 1.05829(14) 0.06003(11) 0.0195(4) Uani 1 1 d . . . . .
N22 N 0.59967(15) 0.89118(15) 0.08175(12) 0.0251(4) Uani 1 1 d . . . . .
O2 O 0.81862(11) 1.11206(11) -0.03894(9) 0.0203(3) Uani 1 1 d . . . . .
C41 C 0.80182(17) 1.20139(16) 0.01673(12) 0.0177(4) Uani 1 1 d . . . . .
H41 H 0.857240 1.231314 0.079582 0.021 Uiso 1 1 calc R U . . .
C42 C 0.67115(17) 1.14539(16) 0.01577(13) 0.0200(4) Uani 1 1 d . . . . .
H42A H 0.651217 1.206324 0.045960 0.024 Uiso 1 1 calc R U . . .
H42B H 0.618505 1.108840 -0.047613 0.024 Uiso 1 1 calc R U . . .
C43 C 0.63500(18) 1.07364(18) 0.14606(14) 0.0255(5) Uani 1 1 d . . . . .
H43 H 0.645722 1.142713 0.188166 0.031 Uiso 1 1 calc R U . . .
C44 C 0.60766(18) 0.97047(19) 0.15867(15) 0.0272(5) Uani 1 1 d . . . . .
H44 H 0.595805 0.955040 0.212161 0.033 Uiso 1 1 calc R U . . .
C45 C 0.62188(17) 0.94713(17) 0.02407(14) 0.0223(5) Uani 1 1 d . . . . .
H45 H 0.622201 0.913664 -0.035095 0.027 Uiso 1 1 calc R U . . .
C51 C 0.82054(16) 1.29955(16) -0.02041(13) 0.0180(4) Uani 1 1 d . . . . .
C52 C 0.81085(18) 1.28189(17) -0.11106(13) 0.0231(5) Uani 1 1 d . . . . .
H52 H 0.796341 1.208436 -0.148729 0.028 Uiso 1 1 calc R U . . .
C53 C 0.82167(18) 1.36801(17) -0.14829(13) 0.0249(5) Uani 1 1 d . . . . .
H53 H 0.815748 1.354287 -0.210308 0.030 Uiso 1 1 calc R U . . .
C54 C 0.84124(18) 1.47429(17) -0.09341(13) 0.0209(4) Uani 1 1 d . . . . .
C55 C 0.85182(17) 1.49645(17) -0.00290(13) 0.0209(4) Uani 1 1 d . . . . .
H55 H 0.865304 1.569781 0.034242 0.025 Uiso 1 1 calc R U . . .
C56 C 0.84227(17) 1.40891(17) 0.03239(12) 0.0188(4) Uani 1 1 d . . . . .
C61 C 0.95418(18) 1.04835(17) -0.09222(13) 0.0190(4) Uani 1 1 d . . . . .
C62 C 0.85570(18) 0.94268(17) -0.14477(13) 0.0225(5) Uani 1 1 d . . . . .
H62 H 0.776837 0.930016 -0.142810 0.027 Uiso 1 1 calc R U . . .
C63 C 0.87060(18) 0.85559(17) -0.19991(14) 0.0248(5) Uani 1 1 d . . . . .
H63 H 0.802608 0.783954 -0.235727 0.030 Uiso 1 1 calc R U . . .
C64 C 0.98474(18) 0.87409(17) -0.20215(13) 0.0209(4) Uani 1 1 d . . . . .
C65 C 1.08514(18) 0.97837(17) -0.15278(13) 0.0216(4) Uani 1 1 d . . . . .
H65 H 1.163531 0.991130 -0.156156 0.026 Uiso 1 1 calc R U . . .
C66 C 1.06728(17) 1.06361(16) -0.09819(13) 0.0199(4) Uani 1 1 d . . . . .
C67 C 0.94299(17) 1.14390(16) -0.03000(13) 0.0201(4) Uani 1 1 d . . . . .
H67A H 0.986967 1.159248 0.033043 0.024 Uiso 1 1 calc R U . . .
H67B H 0.979423 1.215449 -0.044787 0.024 Uiso 1 1 calc R U . . .
O71 O 0.43366(16) 0.26634(14) 0.33720(12) 0.0426(4) Uani 1 1 d . . . . .
H71 H 0.420(3) 0.186(3) 0.354(2) 0.118(13) Uiso 1 1 d . . . . .
O72 O 0.46269(14) 0.18248(13) 0.21114(11) 0.0366(4) Uani 1 1 d . . . . .
O73 O 0.5188(2) 0.72972(17) 0.20219(16) 0.0747(7) Uani 1 1 d . . . . .
O74 O 0.52384(16) 0.67392(15) 0.06182(13) 0.0490(5) Uani 1 1 d . . . . .
H74 H 0.546(2) 0.756(2) 0.0687(18) 0.071(9) Uiso 1 1 d . . . . .
C71 C 0.46270(19) 0.26530(19) 0.26235(17) 0.0311(5) Uani 1 1 d . . . . .
C76 C 0.5032(2) 0.6540(2) 0.1352(2) 0.0452(7) Uani 1 1 d . . . . .
C73 C 0.5336(2) 0.38581(19) 0.16335(18) 0.0405(6) Uani 1 1 d . . . . .
H73A H 0.466586 0.327053 0.109149 0.049 Uiso 1 1 calc R U . . .
H73B H 0.602856 0.367774 0.166741 0.049 Uiso 1 1 calc R U . . .
C72 C 0.4939(2) 0.37922(19) 0.24601(18) 0.0439(7) Uani 1 1 d . . . . .
H72A H 0.422266 0.393740 0.240570 0.053 Uiso 1 1 calc R U . . .
H72B H 0.559385 0.441749 0.299338 0.053 Uiso 1 1 calc R U . . .
C74 C 0.5703(2) 0.5051(2) 0.15410(19) 0.0434(7) Uani 1 1 d . . . . .
H74A H 0.611838 0.510900 0.107267 0.052 Uiso 1 1 calc R U . . .
H74B H 0.628306 0.564691 0.211898 0.052 Uiso 1 1 calc R U . . .
C75 C 0.4611(2) 0.5293(2) 0.1286(2) 0.0498(7) Uani 1 1 d . . . . .
H75A H 0.409818 0.478693 0.066297 0.060 Uiso 1 1 calc R U . . .
H75B H 0.411802 0.511683 0.169660 0.060 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
Cl11 C22 1.7360(19) . ?
Cl12 C24 1.739(2) . ?
Cl13 C36 1.741(2) . ?
Cl14 C34 1.746(2) . ?
N11 C15 1.348(2) . ?
N11 C13 1.372(2) . ?
N11 C12 1.466(2) . ?
N12 C15 1.319(3) . ?
N12 C14 1.373(3) . ?
O1 C11 1.424(2) . ?
O1 C37 1.429(2) . ?
C11 C21 1.518(3) . ?
C11 C12 1.521(3) . ?
C11 H11 1.0000 . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.353(3) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C21 C26 1.389(3) . ?
C21 C22 1.393(3) . ?
C22 C23 1.388(3) . ?
C23 C24 1.374(3) . ?
C23 H23 0.9500 . ?
C24 C25 1.383(3) . ?
C25 C26 1.385(3) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
C31 C32 1.389(3) . ?
C31 C36 1.389(3) . ?
C31 C37 1.498(3) . ?
C32 C33 1.389(3) . ?
C32 H32 0.9500 . ?
C33 C34 1.375(3) . ?
C33 H33 0.9500 . ?
C34 C35 1.380(3) . ?
C35 C36 1.385(3) . ?
C35 H35 0.9500 . ?
C37 H37A 0.9900 . ?
C37 H37B 0.9900 . ?
Cl21 C56 1.7391(19) . ?
Cl22 C54 1.740(2) . ?
Cl23 C66 1.7413(19) . ?
Cl24 C64 1.7457(19) . ?
N21 C45 1.352(2) . ?
N21 C43 1.377(2) . ?
N21 C42 1.460(2) . ?
N22 C45 1.319(2) . ?
N22 C44 1.382(3) . ?
O2 C67 1.426(2) . ?
O2 C41 1.426(2) . ?
C41 C51 1.516(3) . ?
C41 C42 1.516(3) . ?
C41 H41 1.0000 . ?
C42 H42A 0.9900 . ?
C42 H42B 0.9900 . ?
C43 C44 1.356(3) . ?
C43 H43 0.9500 . ?
C44 H44 0.9500 . ?
C45 H45 0.9500 . ?
C51 C52 1.389(3) . ?
C51 C56 1.396(3) . ?
C52 C53 1.386(3) . ?
C52 H52 0.9500 . ?
C53 C54 1.383(3) . ?
C53 H53 0.9500 . ?
C54 C55 1.380(3) . ?
C55 C56 1.386(3) . ?
C55 H55 0.9500 . ?
C61 C66 1.385(3) . ?
C61 C62 1.391(3) . ?
C61 C67 1.497(3) . ?
C62 C63 1.386(3) . ?
C62 H62 0.9500 . ?
C63 C64 1.372(3) . ?
C63 H63 0.9500 . ?
C64 C65 1.382(3) . ?
C65 C66 1.385(3) . ?
C65 H65 0.9500 . ?
C67 H67A 0.9900 . ?
C67 H67B 0.9900 . ?
O71 C71 1.314(3) . ?
O71 H71 1.12(3) . ?
O72 C71 1.213(2) . ?
O73 C76 1.215(3) . ?
O74 C76 1.311(3) . ?
O74 H74 1.00(3) . ?
C71 C72 1.513(3) . ?
C76 C75 1.505(3) . ?
C73 C72 1.506(3) . ?
C73 C74 1.525(3) . ?
C73 H73A 0.9900 . ?
C73 H73B 0.9900 . ?
C72 H72A 0.9900 . ?
C72 H72B 0.9900 . ?
C74 C75 1.543(3) . ?
C74 H74A 0.9900 . ?
C74 H74B 0.9900 . ?
C75 H75A 0.9900 . ?
C75 H75B 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
C15 N11 C13 106.88(17) . . ?
C15 N11 C12 127.86(17) . . ?
C13 N11 C12 125.26(17) . . ?
C15 N12 C14 106.14(18) . . ?
C11 O1 C37 112.84(14) . . ?
O1 C11 C21 112.49(15) . . ?
O1 C11 C12 105.79(15) . . ?
C21 C11 C12 108.77(15) . . ?
O1 C11 H11 109.9 . . ?
C21 C11 H11 109.9 . . ?
C12 C11 H11 109.9 . . ?
N11 C12 C11 113.86(16) . . ?
N11 C12 H12A 108.8 . . ?
C11 C12 H12A 108.8 . . ?
N11 C12 H12B 108.8 . . ?
C11 C12 H12B 108.8 . . ?
H12A C12 H12B 107.7 . . ?
C14 C13 N11 106.69(19) . . ?
C14 C13 H13 126.7 . . ?
N11 C13 H13 126.7 . . ?
C13 C14 N12 109.22(19) . . ?
C13 C14 H14 125.4 . . ?
N12 C14 H14 125.4 . . ?
N12 C15 N11 111.07(19) . . ?
N12 C15 H15 124.5 . . ?
N11 C15 H15 124.5 . . ?
C26 C21 C22 117.21(18) . . ?
C26 C21 C11 120.45(17) . . ?
C22 C21 C11 122.26(17) . . ?
C23 C22 C21 122.45(18) . . ?
C23 C22 Cl11 117.25(15) . . ?
C21 C22 Cl11 120.30(15) . . ?
C24 C23 C22 118.25(18) . . ?
C24 C23 H23 120.9 . . ?
C22 C23 H23 120.9 . . ?
C23 C24 C25 121.40(19) . . ?
C23 C24 Cl12 118.95(16) . . ?
C25 C24 Cl12 119.66(16) . . ?
C24 C25 C26 119.09(19) . . ?
C24 C25 H25 120.5 . . ?
C26 C25 H25 120.5 . . ?
C25 C26 C21 121.60(18) . . ?
C25 C26 H26 119.2 . . ?
C21 C26 H26 119.2 . . ?
C32 C31 C36 117.36(19) . . ?
C32 C31 C37 122.80(18) . . ?
C36 C31 C37 119.84(18) . . ?
C31 C32 C33 121.5(2) . . ?
C31 C32 H32 119.3 . . ?
C33 C32 H32 119.3 . . ?
C34 C33 C32 118.8(2) . . ?
C34 C33 H33 120.6 . . ?
C32 C33 H33 120.6 . . ?
C33 C34 C35 121.89(19) . . ?
C33 C34 Cl14 119.98(16) . . ?
C35 C34 Cl14 118.12(16) . . ?
C34 C35 C36 117.81(19) . . ?
C34 C35 H35 121.1 . . ?
C36 C35 H35 121.1 . . ?
C35 C36 C31 122.61(19) . . ?
C35 C36 Cl13 118.09(16) . . ?
C31 C36 Cl13 119.31(15) . . ?
O1 C37 C31 109.30(16) . . ?
O1 C37 H37A 109.8 . . ?
C31 C37 H37A 109.8 . . ?
O1 C37 H37B 109.8 . . ?
C31 C37 H37B 109.8 . . ?
H37A C37 H37B 108.3 . . ?
C45 N21 C43 107.10(17) . . ?
C45 N21 C42 126.58(16) . . ?
C43 N21 C42 126.32(17) . . ?
C45 N22 C44 105.79(17) . . ?
C67 O2 C41 112.35(14) . . ?
O2 C41 C51 112.11(15) . . ?
O2 C41 C42 105.53(15) . . ?
C51 C41 C42 108.23(15) . . ?
O2 C41 H41 110.3 . . ?
C51 C41 H41 110.3 . . ?
C42 C41 H41 110.3 . . ?
N21 C42 C41 113.96(15) . . ?
N21 C42 H42A 108.8 . . ?
C41 C42 H42A 108.8 . . ?
N21 C42 H42B 108.8 . . ?
C41 C42 H42B 108.8 . . ?
H42A C42 H42B 107.7 . . ?
C44 C43 N21 106.27(18) . . ?
C44 C43 H43 126.9 . . ?
N21 C43 H43 126.9 . . ?
C43 C44 N22 109.58(19) . . ?
C43 C44 H44 125.2 . . ?
N22 C44 H44 125.2 . . ?
N22 C45 N21 111.26(18) . . ?
N22 C45 H45 124.4 . . ?
N21 C45 H45 124.4 . . ?
C52 C51 C56 116.93(18) . . ?
C52 C51 C41 120.49(17) . . ?
C56 C51 C41 122.50(17) . . ?
C53 C52 C51 122.10(18) . . ?
C53 C52 H52 118.9 . . ?
C51 C52 H52 119.0 . . ?
C54 C53 C52 118.71(18) . . ?
C54 C53 H53 120.6 . . ?
C52 C53 H53 120.6 . . ?
C55 C54 C53 121.52(18) . . ?
C55 C54 Cl22 119.30(15) . . ?
C53 C54 Cl22 119.18(15) . . ?
C54 C55 C56 118.25(17) . . ?
C54 C55 H55 120.9 . . ?
C56 C55 H55 120.9 . . ?
C55 C56 C51 122.47(17) . . ?
C55 C56 Cl21 117.56(14) . . ?
C51 C56 Cl21 119.97(15) . . ?
C66 C61 C62 117.43(18) . . ?
C66 C61 C67 119.43(18) . . ?
C62 C61 C67 123.14(18) . . ?
C63 C62 C61 121.19(19) . . ?
C63 C62 H62 119.4 . . ?
C61 C62 H62 119.4 . . ?
C64 C63 C62 119.18(19) . . ?
C64 C63 H63 120.4 . . ?
C62 C63 H63 120.4 . . ?
C63 C64 C65 121.85(18) . . ?
C63 C64 Cl24 119.75(16) . . ?
C65 C64 Cl24 118.40(15) . . ?
C64 C65 C66 117.55(18) . . ?
C64 C65 H65 121.2 . . ?
C66 C65 H65 121.2 . . ?
C65 C66 C61 122.77(18) . . ?
C65 C66 Cl23 118.34(15) . . ?
C61 C66 Cl23 118.88(15) . . ?
O2 C67 C61 109.71(15) . . ?
O2 C67 H67A 109.7 . . ?
C61 C67 H67A 109.7 . . ?
O2 C67 H67B 109.7 . . ?
C61 C67 H67B 109.7 . . ?
H67A C67 H67B 108.2 . . ?
C71 O71 H71 113.1(16) . . ?
C76 O74 H74 109.8(15) . . ?
O72 C71 O71 124.4(2) . . ?
O72 C71 C72 123.6(2) . . ?
O71 C71 C72 112.1(2) . . ?
O73 C76 O74 122.8(2) . . ?
O73 C76 C75 123.7(3) . . ?
O74 C76 C75 113.6(3) . . ?
C72 C73 C74 111.9(2) . . ?
C72 C73 H73A 109.2 . . ?
C74 C73 H73A 109.2 . . ?
C72 C73 H73B 109.2 . . ?
C74 C73 H73B 109.2 . . ?
H73A C73 H73B 107.9 . . ?
C73 C72 C71 114.8(2) . . ?
C73 C72 H72A 108.6 . . ?
C71 C72 H72A 108.6 . . ?
C73 C72 H72B 108.6 . . ?
C71 C72 H72B 108.6 . . ?
H72A C72 H72B 107.5 . . ?
C73 C74 C75 112.43(19) . . ?
C73 C74 H74A 109.1 . . ?
C75 C74 H74A 109.1 . . ?
C73 C74 H74B 109.1 . . ?
C75 C74 H74B 109.1 . . ?
H74A C74 H74B 107.8 . . ?
C76 C75 C74 110.4(2) . . ?
C76 C75 H75A 109.6 . . ?
C74 C75 H75A 109.6 . . ?
C76 C75 H75B 109.6 . . ?
C74 C75 H75B 109.6 . . ?
H75A C75 H75B 108.1 . . ?

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
C37 O1 C11 C21 -72.45(19) . . . . ?
C37 O1 C11 C12 168.94(15) . . . . ?
C15 N11 C12 C11 74.7(2) . . . . ?
C13 N11 C12 C11 -105.3(2) . . . . ?
O1 C11 C12 N11 -75.09(19) . . . . ?
C21 C11 C12 N11 163.85(16) . . . . ?
C15 N11 C13 C14 0.1(2) . . . . ?
C12 N11 C13 C14 -179.84(17) . . . . ?
N11 C13 C14 N12 -0.4(2) . . . . ?
C15 N12 C14 C13 0.6(2) . . . . ?
C14 N12 C15 N11 -0.5(2) . . . . ?
C13 N11 C15 N12 0.2(2) . . . . ?
C12 N11 C15 N12 -179.81(17) . . . . ?
O1 C11 C21 C26 -26.0(2) . . . . ?
C12 C11 C21 C26 90.9(2) . . . . ?
O1 C11 C21 C22 157.26(18) . . . . ?
C12 C11 C21 C22 -85.9(2) . . . . ?
C26 C21 C22 C23 -0.6(3) . . . . ?
C11 C21 C22 C23 176.31(18) . . . . ?
C26 C21 C22 Cl11 -179.79(15) . . . . ?
C11 C21 C22 Cl11 -2.9(3) . . . . ?
C21 C22 C23 C24 0.5(3) . . . . ?
Cl11 C22 C23 C24 179.77(16) . . . . ?
C22 C23 C24 C25 0.0(3) . . . . ?
C22 C23 C24 Cl12 179.56(16) . . . . ?
C23 C24 C25 C26 -0.5(3) . . . . ?
Cl12 C24 C25 C26 179.95(16) . . . . ?
C24 C25 C26 C21 0.5(3) . . . . ?
C22 C21 C26 C25 0.0(3) . . . . ?
C11 C21 C26 C25 -176.89(19) . . . . ?
C36 C31 C32 C33 -0.6(3) . . . . ?
C37 C31 C32 C33 178.74(19) . . . . ?
C31 C32 C33 C34 -0.2(3) . . . . ?
C32 C33 C34 C35 1.3(3) . . . . ?
C32 C33 C34 Cl14 -177.31(16) . . . . ?
C33 C34 C35 C36 -1.4(3) . . . . ?
Cl14 C34 C35 C36 177.20(15) . . . . ?
C34 C35 C36 C31 0.5(3) . . . . ?
C34 C35 C36 Cl13 -179.30(15) . . . . ?
C32 C31 C36 C35 0.5(3) . . . . ?
C37 C31 C36 C35 -178.92(18) . . . . ?
C32 C31 C36 Cl13 -179.70(16) . . . . ?
C37 C31 C36 Cl13 0.9(3) . . . . ?
C11 O1 C37 C31 176.57(15) . . . . ?
C32 C31 C37 O1 5.1(3) . . . . ?
C36 C31 C37 O1 -175.54(16) . . . . ?
C67 O2 C41 C51 74.84(19) . . . . ?
C67 O2 C41 C42 -167.54(15) . . . . ?
C45 N21 C42 C41 -81.0(2) . . . . ?
C43 N21 C42 C41 99.9(2) . . . . ?
O2 C41 C42 N21 66.87(19) . . . . ?
C51 C41 C42 N21 -172.93(15) . . . . ?
C45 N21 C43 C44 0.1(2) . . . . ?
C42 N21 C43 C44 179.37(17) . . . . ?
N21 C43 C44 N22 0.0(2) . . . . ?
C45 N22 C44 C43 -0.1(2) . . . . ?
C44 N22 C45 N21 0.2(2) . . . . ?
C43 N21 C45 N22 -0.2(2) . . . . ?
C42 N21 C45 N22 -179.47(16) . . . . ?
O2 C41 C51 C52 21.3(2) . . . . ?
C42 C41 C51 C52 -94.7(2) . . . . ?
O2 C41 C51 C56 -161.79(17) . . . . ?
C42 C41 C51 C56 82.2(2) . . . . ?
C56 C51 C52 C53 -0.2(3) . . . . ?
C41 C51 C52 C53 176.87(18) . . . . ?
C51 C52 C53 C54 -0.8(3) . . . . ?
C52 C53 C54 C55 0.9(3) . . . . ?
C52 C53 C54 Cl22 179.99(15) . . . . ?
C53 C54 C55 C56 0.0(3) . . . . ?
Cl22 C54 C55 C56 -179.08(14) . . . . ?
C54 C55 C56 C51 -1.1(3) . . . . ?
C54 C55 C56 Cl21 179.45(15) . . . . ?
C52 C51 C56 C55 1.2(3) . . . . ?
C41 C51 C56 C55 -175.84(17) . . . . ?
C52 C51 C56 Cl21 -179.35(14) . . . . ?
C41 C51 C56 Cl21 3.6(3) . . . . ?
C66 C61 C62 C63 0.9(3) . . . . ?
C67 C61 C62 C63 -178.48(18) . . . . ?
C61 C62 C63 C64 0.3(3) . . . . ?
C62 C63 C64 C65 -1.8(3) . . . . ?
C62 C63 C64 Cl24 177.55(15) . . . . ?
C63 C64 C65 C66 1.9(3) . . . . ?
Cl24 C64 C65 C66 -177.45(15) . . . . ?
C64 C65 C66 C61 -0.6(3) . . . . ?
C64 C65 C66 Cl23 -179.64(14) . . . . ?
C62 C61 C66 C65 -0.8(3) . . . . ?
C67 C61 C66 C65 178.62(18) . . . . ?
C62 C61 C66 Cl23 178.28(15) . . . . ?
C67 C61 C66 Cl23 -2.3(3) . . . . ?
C41 O2 C67 C61 -178.12(15) . . . . ?
C66 C61 C67 O2 176.45(16) . . . . ?
C62 C61 C67 O2 -4.2(3) . . . . ?
C74 C73 C72 C71 -176.8(2) . . . . ?
O72 C71 C72 C73 -3.8(3) . . . . ?
O71 C71 C72 C73 177.4(2) . . . . ?
C72 C73 C74 C75 -70.8(3) . . . . ?
O73 C76 C75 C74 -93.0(3) . . . . ?
O74 C76 C75 C74 85.9(3) . . . . ?
C73 C74 C75 C76 170.7(2) . . . . ?

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
O71 H71 N12 1.12(3) 1.50(3) 2.616(2) 172(3) .
O74 H74 N22 1.00(3) 1.60(3) 2.590(2) 172(2) .

_refine_diff_density_max         0.513
_refine_diff_density_min         -0.319
_refine_diff_density_rms         0.061



####################################################################### 
# 
# 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_A
_database_code_depnum_ccdc_archive 'CCDC 2043357'
loop_
_audit_author_name
_audit_author_address
'Andrei Churakov'
;Institute of General and Inorganic Chemistry RAS
Russia
;
_audit_update_record             
;
2020-11-09 deposited with the CCDC.	2021-05-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C18 H14 Cl4 N2 O), H2 O'
_chemical_formula_sum            'C36 H30 Cl8 N4 O3'
_chemical_formula_weight         850.24

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   7.9812(4)
_cell_length_b                   32.6965(16)
_cell_length_c                   14.5964(7)
_cell_angle_alpha                90
_cell_angle_beta                 91.2751(16)
_cell_angle_gamma                90
_cell_volume                     3808.1(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9897
_cell_measurement_theta_min      2.628
_cell_measurement_theta_max      30.518

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.483
_exptl_crystal_F_000             1736
_exptl_transmission_factor_min   0.7662
_exptl_transmission_factor_max   0.8622
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.634
_shelx_estimated_absorpt_T_min   0.884
_shelx_estimated_absorpt_T_max   0.969
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   'SADABS (Bruker, 2016)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            47704
_diffrn_reflns_av_unetI/netI     0.0270
_diffrn_reflns_av_R_equivalents  0.0354
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -41
_diffrn_reflns_limit_k_max       41
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.528
_diffrn_reflns_theta_max         26.997
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             8309
_reflns_number_gt                7843
_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       'APEX3 (Bruker, 2018)'
_computing_cell_refinement       'SAINT (Bruker, 2018)'
_computing_data_reduction        'SAINT (Bruker, 2018)'
_computing_structure_solution    'SHELXT (Sheldrick, 2016)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+9.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         8309
_refine_ls_number_parameters     468
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0700
_refine_ls_R_factor_gt           0.0657
_refine_ls_wR_factor_ref         0.1209
_refine_ls_wR_factor_gt          0.1193
_refine_ls_goodness_of_fit_ref   1.316
_refine_ls_restrained_S_all      1.316
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O -0.1179(3) 0.34630(7) 0.11400(16) 0.0279(5) Uani 1 1 d . . . . .
N11 N 0.1398(4) 0.28334(8) 0.13595(19) 0.0262(6) Uani 1 1 d . . . . .
N12 N 0.3064(5) 0.29469(10) 0.2565(2) 0.0430(9) Uani 1 1 d . . . . .
Cl11 Cl -0.58057(10) 0.30294(3) -0.26352(6) 0.0329(2) Uani 1 1 d . . . . .
Cl12 Cl 0.05921(10) 0.29604(3) -0.14950(6) 0.02662(18) Uani 1 1 d . . . . .
Cl13 Cl -0.17201(15) 0.48066(3) 0.08763(7) 0.0457(3) Uani 1 1 d . . . . .
Cl14 Cl -0.39223(14) 0.47159(3) 0.43237(8) 0.0487(3) Uani 1 1 d . . . . .
C11 C -0.0580(4) 0.32343(10) 0.0390(2) 0.0224(7) Uani 1 1 d . . . . .
H11 H 0.043536 0.336999 0.013940 0.027 Uiso 1 1 calc R U . . .
C12 C -0.0107(4) 0.28154(10) 0.0778(2) 0.0258(7) Uani 1 1 d . . . . .
H12A H -0.104783 0.270883 0.113836 0.031 Uiso 1 1 calc R U . . .
H12B H 0.008040 0.262344 0.026552 0.031 Uiso 1 1 calc R U . . .
C13 C 0.1511(5) 0.29506(11) 0.2247(2) 0.0343(9) Uani 1 1 d . . . . .
H13 H 0.057534 0.302675 0.260021 0.041 Uiso 1 1 calc R U . . .
C14 C 0.3999(5) 0.28253(13) 0.1837(3) 0.0431(10) Uani 1 1 d . . . . .
H14 H 0.518280 0.279538 0.185187 0.052 Uiso 1 1 calc R U . . .
C15 C 0.2995(5) 0.27536(12) 0.1091(3) 0.0350(8) Uani 1 1 d . . . . .
H15 H 0.333341 0.266600 0.050260 0.042 Uiso 1 1 calc R U . . .
C31 C -0.1882(4) 0.40958(10) 0.1820(2) 0.0264(7) Uani 1 1 d . . . . .
C32 C -0.2237(5) 0.38780(11) 0.2603(2) 0.0315(8) Uani 1 1 d . . . . .
H32 H -0.204289 0.359140 0.261330 0.038 Uiso 1 1 calc R U . . .
C33 C -0.2865(5) 0.40640(12) 0.3372(3) 0.0348(8) Uani 1 1 d . . . . .
H33 H -0.310274 0.390800 0.390252 0.042 Uiso 1 1 calc R U . . .
C34 C -0.3141(4) 0.44785(11) 0.3356(3) 0.0306(8) Uani 1 1 d . . . . .
C35 C -0.2801(5) 0.47105(11) 0.2594(3) 0.0336(8) Uani 1 1 d . . . . .
H35 H -0.299112 0.499727 0.258859 0.040 Uiso 1 1 calc R U . . .
C36 C -0.2172(5) 0.45127(10) 0.1835(2) 0.0297(8) Uani 1 1 d . . . . .
C37 C -0.1194(5) 0.38944(10) 0.0986(2) 0.0275(7) Uani 1 1 d . . . . .
H37A H -0.190457 0.396013 0.044056 0.033 Uiso 1 1 calc R U . . .
H37B H -0.004391 0.399355 0.087664 0.033 Uiso 1 1 calc R U . . .
C41 C -0.1911(4) 0.31870(9) -0.0367(2) 0.0205(6) Uani 1 1 d . . . . .
C42 C -0.3596(4) 0.32621(10) -0.0211(2) 0.0262(7) Uani 1 1 d . . . . .
H42 H -0.392560 0.334566 0.038209 0.031 Uiso 1 1 calc R U . . .
C43 C -0.4810(4) 0.32179(10) -0.0902(2) 0.0272(7) Uani 1 1 d . . . . .
H43 H -0.595524 0.327326 -0.078809 0.033 Uiso 1 1 calc R U . . .
C44 C -0.4312(4) 0.30913(10) -0.1758(2) 0.0233(7) Uani 1 1 d . . . . .
C45 C -0.2663(4) 0.30102(10) -0.1940(2) 0.0230(7) Uani 1 1 d . . . . .
H45 H -0.234050 0.292216 -0.253126 0.028 Uiso 1 1 calc R U . . .
C46 C -0.1485(4) 0.30604(9) -0.1241(2) 0.0202(6) Uani 1 1 d . . . . .
O2 O 1.1512(3) 0.39129(6) 0.49960(14) 0.0222(5) Uani 1 1 d . . . . .
N21 N 0.9268(4) 0.32625(8) 0.54242(19) 0.0257(6) Uani 1 1 d . . . . .
N22 N 0.6677(4) 0.31718(11) 0.4909(2) 0.0408(8) Uani 1 1 d . . . . .
Cl21 Cl 1.60559(11) 0.43622(3) 0.88027(6) 0.0319(2) Uani 1 1 d . . . . .
Cl22 Cl 0.97230(10) 0.40069(3) 0.78616(6) 0.02536(17) Uani 1 1 d . . . . .
Cl23 Cl 1.08953(14) 0.51104(3) 0.36431(7) 0.0384(2) Uani 1 1 d . . . . .
Cl24 Cl 1.36281(15) 0.43654(4) 0.07537(6) 0.0512(3) Uani 1 1 d . . . . .
C21 C 1.0955(4) 0.38597(10) 0.5900(2) 0.0205(6) Uani 1 1 d . . . . .
H21 H 0.987077 0.400786 0.597568 0.025 Uiso 1 1 calc R U . . .
C22 C 1.0672(4) 0.34002(10) 0.6005(2) 0.0238(7) Uani 1 1 d . . . . .
H22A H 1.170001 0.325141 0.583647 0.029 Uiso 1 1 calc R U . . .
H22B H 1.043904 0.333711 0.665357 0.029 Uiso 1 1 calc R U . . .
C23 C 0.7623(5) 0.33175(11) 0.5577(3) 0.0325(8) Uani 1 1 d . . . . .
H23 H 0.720023 0.344666 0.610722 0.039 Uiso 1 1 calc R U . . .
C24 C 0.7778(5) 0.30175(13) 0.4288(3) 0.0420(10) Uani 1 1 d . . . . .
H24 H 0.746011 0.289152 0.372388 0.050 Uiso 1 1 calc R U . . .
C25 C 0.9393(5) 0.30700(12) 0.4592(2) 0.0350(9) Uani 1 1 d . . . . .
H25 H 1.038740 0.299062 0.429309 0.042 Uiso 1 1 calc R U . . .
C51 C 1.1839(4) 0.43159(10) 0.3667(2) 0.0207(6) Uani 1 1 d . . . . .
C52 C 1.2500(4) 0.39718(11) 0.3254(2) 0.0271(7) Uani 1 1 d . . . . .
H52 H 1.258533 0.372356 0.359013 0.033 Uiso 1 1 calc R U . . .
C53 C 1.3042(5) 0.39848(12) 0.2353(2) 0.0325(8) Uani 1 1 d . . . . .
H53 H 1.349205 0.374752 0.207513 0.039 Uiso 1 1 calc R U . . .
C54 C 1.2916(5) 0.43461(12) 0.1872(2) 0.0325(8) Uani 1 1 d . . . . .
C55 C 1.2253(5) 0.46947(12) 0.2252(2) 0.0323(8) Uani 1 1 d . . . . .
H55 H 1.216065 0.494158 0.191177 0.039 Uiso 1 1 calc R U . . .
C56 C 1.1728(4) 0.46722(10) 0.3147(2) 0.0243(7) Uani 1 1 d . . . . .
C57 C 1.1255(4) 0.43126(9) 0.4637(2) 0.0213(6) Uani 1 1 d . . . . .
H57A H 1.189704 0.451471 0.500842 0.026 Uiso 1 1 calc R U . . .
H57B H 1.005206 0.438542 0.465457 0.026 Uiso 1 1 calc R U . . .
C61 C 1.2222(4) 0.40060(9) 0.6619(2) 0.0194(6) Uani 1 1 d . . . . .
C62 C 1.3887(4) 0.40697(10) 0.6397(2) 0.0227(7) Uani 1 1 d . . . . .
H62 H 1.421457 0.403532 0.577991 0.027 Uiso 1 1 calc R U . . .
C63 C 1.5082(4) 0.41825(10) 0.7055(2) 0.0244(7) Uani 1 1 d . . . . .
H63 H 1.621208 0.422838 0.689210 0.029 Uiso 1 1 calc R U . . .
C64 C 1.4595(4) 0.42267(10) 0.7955(2) 0.0219(6) Uani 1 1 d . . . . .
C65 C 1.2949(4) 0.41713(9) 0.8205(2) 0.0213(6) Uani 1 1 d . . . . .
H65 H 1.262326 0.420578 0.882228 0.026 Uiso 1 1 calc R U . . .
C66 C 1.1789(4) 0.40638(9) 0.7525(2) 0.0197(6) Uani 1 1 d . . . . .
O10 O 0.3341(4) 0.29413(9) 0.4518(2) 0.0419(7) Uani 1 1 d . . . . .
H1 H 0.335(8) 0.293(2) 0.385(5) 0.10(2) Uiso 1 1 d . . . . .
H2 H 0.433(6) 0.3060(14) 0.469(3) 0.046(13) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C11 1.418(4) . ?
O1 C37 1.428(4) . ?
N11 C13 1.352(4) . ?
N11 C15 1.367(5) . ?
N11 C12 1.457(4) . ?
N12 C13 1.314(5) . ?
N12 C14 1.371(6) . ?
Cl11 C44 1.742(3) . ?
Cl12 C46 1.738(3) . ?
Cl13 C36 1.742(4) . ?
Cl14 C34 1.739(4) . ?
C11 C41 1.522(4) . ?
C11 C12 1.526(4) . ?
C11 H11 1.0000 . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 H13 0.9500 . ?
C14 C15 1.357(6) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C31 C32 1.382(5) . ?
C31 C36 1.383(5) . ?
C31 C37 1.500(5) . ?
C32 C33 1.380(5) . ?
C32 H32 0.9500 . ?
C33 C34 1.373(5) . ?
C33 H33 0.9500 . ?
C34 C35 1.379(5) . ?
C35 C36 1.386(5) . ?
C35 H35 0.9500 . ?
C37 H37A 0.9900 . ?
C37 H37B 0.9900 . ?
C41 C46 1.391(4) . ?
C41 C42 1.391(5) . ?
C42 C43 1.390(5) . ?
C42 H42 0.9500 . ?
C43 C44 1.384(5) . ?
C43 H43 0.9500 . ?
C44 C45 1.375(4) . ?
C45 C46 1.382(4) . ?
C45 H45 0.9500 . ?
O2 C21 1.412(4) . ?
O2 C57 1.421(4) . ?
N21 C23 1.349(5) . ?
N21 C25 1.374(4) . ?
N21 C22 1.461(4) . ?
N22 C23 1.310(5) . ?
N22 C24 1.373(6) . ?
Cl21 C64 1.739(3) . ?
Cl22 C66 1.741(3) . ?
Cl23 C56 1.744(3) . ?
Cl24 C54 1.742(4) . ?
C21 C61 1.519(4) . ?
C21 C22 1.527(4) . ?
C21 H21 1.0000 . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 H23 0.9500 . ?
C24 C25 1.365(6) . ?
C24 H24 0.9500 . ?
C25 H25 0.9500 . ?
C51 C52 1.386(5) . ?
C51 C56 1.392(4) . ?
C51 C57 1.501(4) . ?
C52 C53 1.394(5) . ?
C52 H52 0.9500 . ?
C53 C54 1.377(5) . ?
C53 H53 0.9500 . ?
C54 C55 1.379(6) . ?
C55 C56 1.382(5) . ?
C55 H55 0.9500 . ?
C57 H57A 0.9900 . ?
C57 H57B 0.9900 . ?
C61 C66 1.388(4) . ?
C61 C62 1.390(4) . ?
C62 C63 1.389(5) . ?
C62 H62 0.9500 . ?
C63 C64 1.385(5) . ?
C63 H63 0.9500 . ?
C64 C65 1.383(4) . ?
C65 C66 1.387(4) . ?
C65 H65 0.9500 . ?
O10 H1 0.98(7) . ?
O10 H2 0.91(5) . ?

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
C11 O1 C37 113.6(3) . . ?
C13 N11 C15 106.6(3) . . ?
C13 N11 C12 127.4(3) . . ?
C15 N11 C12 125.9(3) . . ?
C13 N12 C14 104.7(3) . . ?
O1 C11 C41 111.8(3) . . ?
O1 C11 C12 105.8(3) . . ?
C41 C11 C12 109.9(3) . . ?
O1 C11 H11 109.8 . . ?
C41 C11 H11 109.8 . . ?
C12 C11 H11 109.8 . . ?
N11 C12 C11 112.0(3) . . ?
N11 C12 H12A 109.2 . . ?
C11 C12 H12A 109.2 . . ?
N11 C12 H12B 109.2 . . ?
C11 C12 H12B 109.2 . . ?
H12A C12 H12B 107.9 . . ?
N12 C13 N11 112.2(4) . . ?
N12 C13 H13 123.9 . . ?
N11 C13 H13 123.9 . . ?
C15 C14 N12 110.5(4) . . ?
C15 C14 H14 124.7 . . ?
N12 C14 H14 124.7 . . ?
C14 C15 N11 105.9(4) . . ?
C14 C15 H15 127.0 . . ?
N11 C15 H15 127.0 . . ?
C32 C31 C36 117.3(3) . . ?
C32 C31 C37 122.1(3) . . ?
C36 C31 C37 120.6(3) . . ?
C33 C32 C31 122.0(3) . . ?
C33 C32 H32 119.0 . . ?
C31 C32 H32 119.0 . . ?
C34 C33 C32 118.8(4) . . ?
C34 C33 H33 120.6 . . ?
C32 C33 H33 120.6 . . ?
C33 C34 C35 121.5(3) . . ?
C33 C34 Cl14 119.2(3) . . ?
C35 C34 Cl14 119.4(3) . . ?
C34 C35 C36 118.0(3) . . ?
C34 C35 H35 121.0 . . ?
C36 C35 H35 121.0 . . ?
C31 C36 C35 122.4(3) . . ?
C31 C36 Cl13 119.6(3) . . ?
C35 C36 Cl13 118.0(3) . . ?
O1 C37 C31 107.9(3) . . ?
O1 C37 H37A 110.1 . . ?
C31 C37 H37A 110.1 . . ?
O1 C37 H37B 110.1 . . ?
C31 C37 H37B 110.1 . . ?
H37A C37 H37B 108.4 . . ?
C46 C41 C42 117.3(3) . . ?
C46 C41 C11 121.0(3) . . ?
C42 C41 C11 121.7(3) . . ?
C43 C42 C41 121.6(3) . . ?
C43 C42 H42 119.2 . . ?
C41 C42 H42 119.2 . . ?
C44 C43 C42 118.5(3) . . ?
C44 C43 H43 120.8 . . ?
C42 C43 H43 120.8 . . ?
C45 C44 C43 121.9(3) . . ?
C45 C44 Cl11 118.6(3) . . ?
C43 C44 Cl11 119.6(3) . . ?
C44 C45 C46 118.2(3) . . ?
C44 C45 H45 120.9 . . ?
C46 C45 H45 120.9 . . ?
C45 C46 C41 122.5(3) . . ?
C45 C46 Cl12 117.1(2) . . ?
C41 C46 Cl12 120.4(2) . . ?
C21 O2 C57 114.3(2) . . ?
C23 N21 C25 107.3(3) . . ?
C23 N21 C22 126.8(3) . . ?
C25 N21 C22 125.8(3) . . ?
C23 N22 C24 105.0(3) . . ?
O2 C21 C61 112.8(3) . . ?
O2 C21 C22 105.4(3) . . ?
C61 C21 C22 109.7(2) . . ?
O2 C21 H21 109.6 . . ?
C61 C21 H21 109.6 . . ?
C22 C21 H21 109.6 . . ?
N21 C22 C21 111.0(3) . . ?
N21 C22 H22A 109.4 . . ?
C21 C22 H22A 109.4 . . ?
N21 C22 H22B 109.4 . . ?
C21 C22 H22B 109.4 . . ?
H22A C22 H22B 108.0 . . ?
N22 C23 N21 112.1(4) . . ?
N22 C23 H23 124.0 . . ?
N21 C23 H23 124.0 . . ?
C25 C24 N22 110.7(3) . . ?
C25 C24 H24 124.7 . . ?
N22 C24 H24 124.7 . . ?
C24 C25 N21 105.0(4) . . ?
C24 C25 H25 127.5 . . ?
N21 C25 H25 127.5 . . ?
C52 C51 C56 117.5(3) . . ?
C52 C51 C57 122.2(3) . . ?
C56 C51 C57 120.2(3) . . ?
C51 C52 C53 120.9(3) . . ?
C51 C52 H52 119.5 . . ?
C53 C52 H52 119.5 . . ?
C54 C53 C52 119.1(3) . . ?
C54 C53 H53 120.4 . . ?
C52 C53 H53 120.4 . . ?
C53 C54 C55 121.9(3) . . ?
C53 C54 Cl24 119.2(3) . . ?
C55 C54 Cl24 118.9(3) . . ?
C54 C55 C56 117.6(3) . . ?
C54 C55 H55 121.2 . . ?
C56 C55 H55 121.2 . . ?
C55 C56 C51 122.9(3) . . ?
C55 C56 Cl23 118.4(3) . . ?
C51 C56 Cl23 118.8(3) . . ?
O2 C57 C51 108.0(3) . . ?
O2 C57 H57A 110.1 . . ?
C51 C57 H57A 110.1 . . ?
O2 C57 H57B 110.1 . . ?
C51 C57 H57B 110.1 . . ?
H57A C57 H57B 108.4 . . ?
C66 C61 C62 117.5(3) . . ?
C66 C61 C21 121.7(3) . . ?
C62 C61 C21 120.7(3) . . ?
C63 C62 C61 121.6(3) . . ?
C63 C62 H62 119.2 . . ?
C61 C62 H62 119.2 . . ?
C64 C63 C62 118.7(3) . . ?
C64 C63 H63 120.6 . . ?
C62 C63 H63 120.6 . . ?
C65 C64 C63 121.7(3) . . ?
C65 C64 Cl21 118.1(2) . . ?
C63 C64 Cl21 120.2(2) . . ?
C64 C65 C66 117.8(3) . . ?
C64 C65 H65 121.1 . . ?
C66 C65 H65 121.1 . . ?
C65 C66 C61 122.7(3) . . ?
C65 C66 Cl22 116.5(2) . . ?
C61 C66 Cl22 120.8(2) . . ?
H1 O10 H2 105(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
C37 O1 C11 C41 -78.7(3) . . . . ?
C37 O1 C11 C12 161.7(3) . . . . ?
C13 N11 C12 C11 81.0(4) . . . . ?
C15 N11 C12 C11 -95.3(4) . . . . ?
O1 C11 C12 N11 -71.4(3) . . . . ?
C41 C11 C12 N11 167.8(3) . . . . ?
C14 N12 C13 N11 0.7(4) . . . . ?
C15 N11 C13 N12 -0.7(4) . . . . ?
C12 N11 C13 N12 -177.6(3) . . . . ?
C13 N12 C14 C15 -0.5(4) . . . . ?
N12 C14 C15 N11 0.1(4) . . . . ?
C13 N11 C15 C14 0.3(4) . . . . ?
C12 N11 C15 C14 177.3(3) . . . . ?
C36 C31 C32 C33 0.4(5) . . . . ?
C37 C31 C32 C33 179.8(3) . . . . ?
C31 C32 C33 C34 -0.1(6) . . . . ?
C32 C33 C34 C35 -0.2(6) . . . . ?
C32 C33 C34 Cl14 -179.7(3) . . . . ?
C33 C34 C35 C36 0.2(6) . . . . ?
Cl14 C34 C35 C36 179.7(3) . . . . ?
C32 C31 C36 C35 -0.3(5) . . . . ?
C37 C31 C36 C35 -179.8(3) . . . . ?
C32 C31 C36 Cl13 179.0(3) . . . . ?
C37 C31 C36 Cl13 -0.4(5) . . . . ?
C34 C35 C36 C31 0.0(6) . . . . ?
C34 C35 C36 Cl13 -179.3(3) . . . . ?
C11 O1 C37 C31 178.9(3) . . . . ?
C32 C31 C37 O1 6.0(5) . . . . ?
C36 C31 C37 O1 -174.6(3) . . . . ?
O1 C11 C41 C46 164.7(3) . . . . ?
C12 C11 C41 C46 -78.2(4) . . . . ?
O1 C11 C41 C42 -16.3(4) . . . . ?
C12 C11 C41 C42 100.9(4) . . . . ?
C46 C41 C42 C43 -0.8(5) . . . . ?
C11 C41 C42 C43 -179.8(3) . . . . ?
C41 C42 C43 C44 0.8(5) . . . . ?
C42 C43 C44 C45 -0.2(5) . . . . ?
C42 C43 C44 Cl11 179.5(3) . . . . ?
C43 C44 C45 C46 -0.3(5) . . . . ?
Cl11 C44 C45 C46 179.9(2) . . . . ?
C44 C45 C46 C41 0.3(5) . . . . ?
C44 C45 C46 Cl12 -179.4(2) . . . . ?
C42 C41 C46 C45 0.3(5) . . . . ?
C11 C41 C46 C45 179.3(3) . . . . ?
C42 C41 C46 Cl12 179.9(2) . . . . ?
C11 C41 C46 Cl12 -1.0(4) . . . . ?
C57 O2 C21 C61 -82.7(3) . . . . ?
C57 O2 C21 C22 157.5(3) . . . . ?
C23 N21 C22 C21 -75.9(4) . . . . ?
C25 N21 C22 C21 100.5(4) . . . . ?
O2 C21 C22 N21 -67.4(3) . . . . ?
C61 C21 C22 N21 170.8(3) . . . . ?
C24 N22 C23 N21 -0.5(4) . . . . ?
C25 N21 C23 N22 0.5(4) . . . . ?
C22 N21 C23 N22 177.5(3) . . . . ?
C23 N22 C24 C25 0.3(5) . . . . ?
N22 C24 C25 N21 0.0(4) . . . . ?
C23 N21 C25 C24 -0.3(4) . . . . ?
C22 N21 C25 C24 -177.3(3) . . . . ?
C56 C51 C52 C53 0.4(5) . . . . ?
C57 C51 C52 C53 -179.6(3) . . . . ?
C51 C52 C53 C54 0.1(5) . . . . ?
C52 C53 C54 C55 -0.7(6) . . . . ?
C52 C53 C54 Cl24 178.8(3) . . . . ?
C53 C54 C55 C56 0.7(6) . . . . ?
Cl24 C54 C55 C56 -178.8(3) . . . . ?
C54 C55 C56 C51 -0.2(5) . . . . ?
C54 C55 C56 Cl23 179.7(3) . . . . ?
C52 C51 C56 C55 -0.4(5) . . . . ?
C57 C51 C56 C55 179.6(3) . . . . ?
C52 C51 C56 Cl23 179.8(2) . . . . ?
C57 C51 C56 Cl23 -0.2(4) . . . . ?
C21 O2 C57 C51 -177.6(2) . . . . ?
C52 C51 C57 O2 -0.1(4) . . . . ?
C56 C51 C57 O2 179.9(3) . . . . ?
O2 C21 C61 C66 165.8(3) . . . . ?
C22 C21 C61 C66 -77.0(4) . . . . ?
O2 C21 C61 C62 -17.1(4) . . . . ?
C22 C21 C61 C62 100.1(3) . . . . ?
C66 C61 C62 C63 0.7(5) . . . . ?
C21 C61 C62 C63 -176.5(3) . . . . ?
C61 C62 C63 C64 0.8(5) . . . . ?
C62 C63 C64 C65 -1.6(5) . . . . ?
C62 C63 C64 Cl21 179.3(3) . . . . ?
C63 C64 C65 C66 0.8(5) . . . . ?
Cl21 C64 C65 C66 179.9(2) . . . . ?
C64 C65 C66 C61 0.8(5) . . . . ?
C64 C65 C66 Cl22 -178.7(2) . . . . ?
C62 C61 C66 C65 -1.5(5) . . . . ?
C21 C61 C66 C65 175.7(3) . . . . ?
C62 C61 C66 Cl22 178.0(2) . . . . ?
C21 C61 C66 Cl22 -4.8(4) . . . . ?

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
O10 H1 N12 0.98(7) 1.88(7) 2.854(5) 173(6) .
O10 H2 N22 0.91(5) 1.93(5) 2.814(4) 164(4) .

_refine_diff_density_max         0.687
_refine_diff_density_min         -0.405
_refine_diff_density_rms         0.073

