# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 2012316'
_audit_update_record             
;
2020-06-25 deposited with the CCDC.	2021-04-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H19 Br3 N4 O'
_chemical_formula_weight         571.12

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_H-M_alt        'C c'
_space_group_name_Hall           'C -2yc'

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

_cell_length_a                   4.8625(6)
_cell_length_b                   27.236(3)
_cell_length_c                   16.031(2)
_cell_angle_alpha                90
_cell_angle_beta                 97.220(4)
_cell_angle_gamma                90
_cell_volume                     2106.2(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    2560
_cell_measurement_theta_min      1.5
_cell_measurement_theta_max      25.0

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.801
_exptl_crystal_F_000             1120
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.06
_exptl_absorpt_coefficient_mu    5.764
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.47
_exptl_absorpt_correction_T_max  0.71
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      273(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker SMART APEX II CCD area-detector'
_diffrn_measurement_method       'ω and φ'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13375
_diffrn_reflns_av_unetI/netI     0.0645
_diffrn_reflns_av_R_equivalents  0.0472
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -34
_diffrn_reflns_limit_k_max       34
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.969
_diffrn_reflns_theta_max         27.144
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4642
_reflns_number_gt                3559
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.993
_reflns_Friedel_fraction_max     0.999
_reflns_Friedel_fraction_full    0.999

_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       'APEX2 (Bruker, 2007)'
_computing_cell_refinement       'APEX2(Bruker,2007)and SAINT (Bruker,2007)'
_computing_data_reduction        'SAINT(Bruker,2007)and XPREP(Bruker,2007)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    
;    
ORTEP-3 for Windows (Farrugia, 1997), DIAMOND (Brandenburg,
1999) and Mercury (Macrae et al., 2006)
;
_computing_publication_material  'PLATON (Spek, 2009)'
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0353P)²+0.9192P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.11(2)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         4642
_refine_ls_number_parameters     260
_refine_ls_number_restraints     5
_refine_ls_R_factor_all          0.0718
_refine_ls_R_factor_gt           0.0427
_refine_ls_wR_factor_ref         0.0954
_refine_ls_wR_factor_gt          0.0854
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_restrained_S_all      1.064
_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
Br3 Br 0.47498(16) 0.54427(3) 0.18616(7) 0.0548(3) Uani 1 1 d . . . . .
Br2 Br 0.52614(18) 0.72522(4) 0.81399(7) 0.0590(3) Uani 1 1 d . . . . .
Br1 Br 0.92544(15) 0.94275(3) 0.37253(6) 0.0590(3) Uani 1 1 d . . . . .
N1 N 0.4683(13) 0.6282(2) 0.5265(4) 0.0341(13) Uani 1 1 d . . . . .
N2 N -0.1879(14) 0.5703(3) 0.7169(5) 0.0455(18) Uani 1 1 d . . . . .
H2A H -0.298064 0.553300 0.743374 0.055 Uiso 1 1 calc R U . . .
N4 N 0.6178(17) 0.8616(3) 0.4737(5) 0.060(2) Uani 1 1 d . . . . .
H4A H 0.704865 0.876907 0.438152 0.071 Uiso 1 1 calc R U . . .
C11 C 0.1472(14) 0.6250(3) 0.6297(5) 0.0311(17) Uani 1 1 d . . . . .
N3 N 1.0949(14) 0.5662(3) 0.3314(5) 0.050(2) Uani 1 1 d . . . . .
H3A H 1.198320 0.548327 0.303965 0.060 Uiso 1 1 calc R U . . .
C12 C -0.0023(18) 0.6467(3) 0.6880(6) 0.0421(19) Uani 1 1 d . . . . .
H12 H 0.010246 0.680310 0.697583 0.050 Uiso 1 1 calc R U . . .
C9 C 0.6196(14) 0.6534(3) 0.4758(5) 0.0316(16) Uani 1 1 d . . . . .
C15 C 0.1288(17) 0.5745(3) 0.6194(6) 0.0409(19) Uani 1 1 d . . . . .
H15 H 0.233757 0.558794 0.582721 0.049 Uiso 1 1 calc R U . . .
C10 C 0.6284(16) 0.7040(3) 0.4746(5) 0.0356(17) Uani 1 1 d . . . . .
H10 H 0.735176 0.719904 0.438663 0.043 Uiso 1 1 calc R U . . .
C14 C -0.045(2) 0.5477(3) 0.6635(6) 0.047(2) Uani 1 1 d . . . . .
H14 H -0.060990 0.513933 0.655717 0.057 Uiso 1 1 calc R U . . .
C7 C 0.3204(15) 0.7051(3) 0.5793(5) 0.0345(17) Uani 1 1 d . . . . .
H7 H 0.217757 0.721543 0.615854 0.041 Uiso 1 1 calc R U . . .
C8 C 0.3179(14) 0.6543(3) 0.5764(5) 0.0303(16) Uani 1 1 d . . . . .
C16 C 0.7846(15) 0.6231(3) 0.4233(5) 0.0365(18) Uani 1 1 d . . . . .
C18 C 1.1024(17) 0.6146(4) 0.3218(6) 0.049(2) Uani 1 1 d . . . . .
H18 H 1.209863 0.628497 0.283923 0.059 Uiso 1 1 calc R U . . .
C4 C 0.4814(16) 0.7856(3) 0.5274(5) 0.0346(16) Uani 1 1 d . . . . .
C6 C 0.4764(16) 0.7318(3) 0.5276(5) 0.0314(15) Uani 1 1 d . . . . .
C17 C 0.9486(17) 0.6444(3) 0.3689(6) 0.0433(19) Uani 1 1 d . . . . .
H17 H 0.955875 0.678392 0.363845 0.052 Uiso 1 1 calc R U . . .
C1 C 0.498(2) 0.8867(3) 0.5267(7) 0.057(3) Uani 1 1 d . . . . .
H1 H 0.506044 0.920822 0.526157 0.069 Uiso 1 1 calc R U . . .
C20 C 0.7768(17) 0.5723(3) 0.4286(5) 0.0406(19) Uani 1 1 d . . . . .
H20 H 0.665287 0.556998 0.463921 0.049 Uiso 1 1 calc R U . . .
C5 C 0.6123(19) 0.8120(3) 0.4718(6) 0.052(2) Uani 1 1 d . . . . .
H5 H 0.699624 0.795556 0.431621 0.062 Uiso 1 1 calc R U . . .
C13 C -0.1685(17) 0.6184(3) 0.7314(6) 0.047(2) Uani 1 1 d . . . . .
H13 H -0.267788 0.632687 0.770987 0.056 Uiso 1 1 calc R U . . .
C2 C 0.358(3) 0.8633(4) 0.5837(7) 0.074(3) Uani 1 1 d . . . . .
H2 H 0.269993 0.881207 0.622041 0.089 Uiso 1 1 calc R U . . .
C19 C 0.937(2) 0.5446(3) 0.3806(7) 0.054(2) Uani 1 1 d . . . . .
H19 H 0.933124 0.510479 0.383357 0.065 Uiso 1 1 calc R U . . .
O1 O 0.971(2) 0.7878(5) 0.7254(7) 0.114(3) Uani 1 1 d D . . . .
H1A H 1.137(12) 0.779(7) 0.734(12) 0.171 Uiso 1 1 d D U . . .
H1B H 0.85(2) 0.774(6) 0.749(11) 0.171 Uiso 1 1 d D U . . .
C3 C 0.349(2) 0.8130(3) 0.5839(6) 0.062(3) Uani 1 1 d . . . . .
H3 H 0.253204 0.796832 0.622386 0.075 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
N1 C9 1.350(9) . ?
N1 C8 1.351(9) . ?
N2 C14 1.323(12) . ?
N2 C13 1.329(11) . ?
N2 H2A 0.8600 . ?
N4 C1 1.288(11) . ?
N4 C5 1.349(11) . ?
N4 H4A 0.8600 . ?
C11 C12 1.385(11) . ?
C11 C15 1.387(11) . ?
C11 C8 1.495(10) . ?
N3 C19 1.306(12) . ?
N3 C18 1.329(11) . ?
N3 H3A 0.8600 . ?
C12 C13 1.369(11) . ?
C12 H12 0.9300 . ?
C9 C10 1.377(10) . ?
C9 C16 1.484(10) . ?
C15 C14 1.376(13) . ?
C15 H15 0.9300 . ?
C10 C6 1.415(10) . ?
C10 H10 0.9300 . ?
C14 H14 0.9300 . ?
C7 C8 1.386(10) . ?
C7 C6 1.396(10) . ?
C7 H7 0.9300 . ?
C16 C17 1.381(11) . ?
C16 C20 1.388(11) . ?
C18 C17 1.389(12) . ?
C18 H18 0.9300 . ?
C4 C5 1.365(11) . ?
C4 C3 1.390(11) . ?
C4 C6 1.465(10) . ?
C17 H17 0.9300 . ?
C1 C2 1.363(13) . ?
C1 H1 0.9300 . ?
C20 C19 1.388(12) . ?
C20 H20 0.9300 . ?
C5 H5 0.9300 . ?
C13 H13 0.9300 . ?
C2 C3 1.372(13) . ?
C2 H2 0.9300 . ?
C19 H19 0.9300 . ?
O1 H1A 0.83(3) . ?
O1 H1B 0.84(3) . ?
C3 H3 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C9 N1 C8 117.7(6) . . ?
C14 N2 C13 122.7(7) . . ?
C14 N2 H2A 118.6 . . ?
C13 N2 H2A 118.6 . . ?
C1 N4 C5 122.5(8) . . ?
C1 N4 H4A 118.7 . . ?
C5 N4 H4A 118.7 . . ?
C12 C11 C15 118.1(7) . . ?
C12 C11 C8 122.4(7) . . ?
C15 C11 C8 119.5(7) . . ?
C19 N3 C18 123.0(7) . . ?
C19 N3 H3A 118.5 . . ?
C18 N3 H3A 118.5 . . ?
C13 C12 C11 119.8(8) . . ?
C13 C12 H12 120.1 . . ?
C11 C12 H12 120.1 . . ?
N1 C9 C10 122.5(6) . . ?
N1 C9 C16 115.6(6) . . ?
C10 C9 C16 121.9(7) . . ?
C14 C15 C11 120.0(8) . . ?
C14 C15 H15 120.0 . . ?
C11 C15 H15 120.0 . . ?
C9 C10 C6 120.5(7) . . ?
C9 C10 H10 119.7 . . ?
C6 C10 H10 119.7 . . ?
N2 C14 C15 119.4(8) . . ?
N2 C14 H14 120.3 . . ?
C15 C14 H14 120.3 . . ?
C8 C7 C6 120.2(7) . . ?
C8 C7 H7 119.9 . . ?
C6 C7 H7 119.9 . . ?
N1 C8 C7 122.9(7) . . ?
N1 C8 C11 116.0(6) . . ?
C7 C8 C11 121.1(6) . . ?
C17 C16 C20 118.7(7) . . ?
C17 C16 C9 121.4(7) . . ?
C20 C16 C9 120.0(7) . . ?
N3 C18 C17 119.5(8) . . ?
N3 C18 H18 120.2 . . ?
C17 C18 H18 120.2 . . ?
C5 C4 C3 115.8(8) . . ?
C5 C4 C6 122.5(7) . . ?
C3 C4 C6 121.7(7) . . ?
C7 C6 C10 116.2(6) . . ?
C7 C6 C4 122.1(7) . . ?
C10 C6 C4 121.7(7) . . ?
C16 C17 C18 119.4(8) . . ?
C16 C17 H17 120.3 . . ?
C18 C17 H17 120.3 . . ?
N4 C1 C2 119.9(8) . . ?
N4 C1 H1 120.0 . . ?
C2 C1 H1 120.0 . . ?
C19 C20 C16 119.2(8) . . ?
C19 C20 H20 120.4 . . ?
C16 C20 H20 120.4 . . ?
N4 C5 C4 121.4(8) . . ?
N4 C5 H5 119.3 . . ?
C4 C5 H5 119.3 . . ?
N2 C13 C12 119.9(8) . . ?
N2 C13 H13 120.1 . . ?
C12 C13 H13 120.1 . . ?
C1 C2 C3 119.1(9) . . ?
C1 C2 H2 120.4 . . ?
C3 C2 H2 120.4 . . ?
N3 C19 C20 120.2(8) . . ?
N3 C19 H19 119.9 . . ?
C20 C19 H19 119.9 . . ?
H1A O1 H1B 122(9) . . ?
C2 C3 C4 121.2(9) . . ?
C2 C3 H3 119.4 . . ?
C4 C3 H3 119.4 . . ?

_refine_diff_density_max         0.567
_refine_diff_density_min         -0.328
_refine_diff_density_rms         0.075

####################################################################### 
# 
# 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_shelx_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2012317'
_audit_update_record             
;
2021-03-25 deposited with the CCDC.	2021-04-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H17 N4, 3(Cl), 2(H2 O)'
_chemical_formula_sum            'C20 H21 Cl3 N4 O2'
_chemical_formula_weight         455.76

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'
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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_H-M_alt        'C c'
_space_group_name_Hall           'C -2yc'

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

_cell_length_a                   4.6889(2)
_cell_length_b                   27.4022(12)
_cell_length_c                   16.2907(7)
_cell_angle_alpha                90
_cell_angle_beta                 95.444(2)
_cell_angle_gamma                90
_cell_volume                     2083.69(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1850
_cell_measurement_theta_min      1.5
_cell_measurement_theta_max      25.0

_exptl_crystal_description       block
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.453
_exptl_crystal_F_000             944
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.06
_exptl_absorpt_coefficient_mu    0.465
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.94
_exptl_absorpt_correction_T_max  0.97
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker SMART APEX II CCD area-detector'
_diffrn_measurement_method       'ω and φ'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12776
_diffrn_reflns_av_unetI/netI     0.0306
_diffrn_reflns_av_R_equivalents  0.0303
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.946
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_point_group_measured_fraction_full 0.967
_reflns_number_total             3568
_reflns_number_gt                3327
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.936
_reflns_Friedel_fraction_max     0.939
_reflns_Friedel_fraction_full    0.939

_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;

_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_cell_refinement       'APEX2(Bruker,2007)and SAINT (Bruker,2007)'
_computing_data_reduction        'SAINT(Bruker,2007)and XPREP(Bruker,2007)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    
;    
ORTEP-3 for Windows (Farrugia, 1997), DIAMOND (Brandenburg,
1999) and Mercury (Macrae et al., 2006)
;
_computing_publication_material  'PLATON (Spek, 2009)'
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0507P)²+0.1498P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.01(8)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3568
_refine_ls_number_parameters     275
_refine_ls_number_restraints     8
_refine_ls_R_factor_all          0.0352
_refine_ls_R_factor_gt           0.0319
_refine_ls_wR_factor_ref         0.0815
_refine_ls_wR_factor_gt          0.0794
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.044
_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
Cl1 Cl 0.1152(2) 0.06256(3) 0.55855(6) 0.0531(3) Uani 1 1 d . . . . .
Cl3 Cl 0.4996(2) 0.45814(3) 0.71899(6) 0.0509(3) Uani 1 1 d . . . . .
Cl2 Cl 0.4995(2) 0.27680(4) 0.10457(7) 0.0573(3) Uani 1 1 d . . . . .
N1 N 0.5363(6) 0.36526(9) 0.39401(17) 0.0305(5) Uani 1 1 d . . . . .
N2 N 1.1997(6) 0.42679(11) 0.20042(18) 0.0379(7) Uani 1 1 d . . . . .
H2A H 1.308097 0.444564 0.172918 0.046 Uiso 1 1 calc R U . . .
N4 N 0.4209(8) 0.13417(11) 0.4538(2) 0.0492(8) Uani 1 1 d . . . . .
H4A H 0.343001 0.118923 0.492049 0.059 Uiso 1 1 calc R U . . .
N3 N -0.1103(7) 0.42705(12) 0.59223(18) 0.0434(8) Uani 1 1 d . . . . .
H3A H -0.212768 0.444820 0.621556 0.052 Uiso 1 1 calc R U . . .
C11 C 0.8663(7) 0.37024(11) 0.29077(18) 0.0284(7) Uani 1 1 d . . . . .
C8 C 0.6927(7) 0.34017(11) 0.34384(19) 0.0283(6) Uani 1 1 d . . . . .
C15 C 0.8725(8) 0.42060(12) 0.2997(2) 0.0348(7) Uani 1 1 d . . . . .
H15 H 0.761249 0.435592 0.336782 0.042 Uiso 1 1 calc R U . . .
C14 C 1.0425(8) 0.44821(13) 0.2540(2) 0.0396(8) Uani 1 1 d . . . . .
H14 H 1.048146 0.481935 0.260402 0.048 Uiso 1 1 calc R U . . .
C18 C -0.1143(8) 0.37893(15) 0.6016(2) 0.0424(9) Uani 1 1 d . . . . .
H18 H -0.224664 0.365144 0.640120 0.051 Uiso 1 1 calc R U . . .
C9 C 0.3800(7) 0.34019(11) 0.44485(18) 0.0296(7) Uani 1 1 d . . . . .
C10 C 0.3788(7) 0.28963(12) 0.4475(2) 0.0342(7) Uani 1 1 d . . . . .
H10 H 0.271747 0.273411 0.484220 0.041 Uiso 1 1 calc R U . . .
C16 C 0.2098(7) 0.37059(12) 0.49834(19) 0.0305(7) Uani 1 1 d . . . . .
C17 C 0.0421(7) 0.34952(13) 0.5553(2) 0.0376(8) Uani 1 1 d . . . . .
H17 H 0.037058 0.315810 0.561532 0.045 Uiso 1 1 calc R U . . .
C13 C 1.1947(8) 0.37866(13) 0.1880(2) 0.0386(8) Uani 1 1 d . . . . .
H13 H 1.304322 0.364953 0.149237 0.046 Uiso 1 1 calc R U . . .
C6 C 0.5388(8) 0.26316(11) 0.3949(2) 0.0321(6) Uani 1 1 d . . . . .
C7 C 0.6993(7) 0.28955(12) 0.3425(2) 0.0336(7) Uani 1 1 d . . . . .
H7 H 0.810414 0.273317 0.306865 0.040 Uiso 1 1 calc R U . . .
C12 C 1.0291(8) 0.34958(12) 0.2319(2) 0.0366(8) Uani 1 1 d . . . . .
H12 H 1.024121 0.316074 0.222821 0.044 Uiso 1 1 calc R U . . .
C5 C 0.4230(9) 0.18275(13) 0.4555(2) 0.0430(9) Uani 1 1 d . . . . .
H5 H 0.343512 0.199143 0.497833 0.052 Uiso 1 1 calc R U . . .
C4 C 0.5417(8) 0.20890(12) 0.3951(2) 0.0358(7) Uani 1 1 d . . . . .
C20 C 0.2106(8) 0.42095(13) 0.4910(2) 0.0376(8) Uani 1 1 d . . . . .
H20 H 0.321190 0.436014 0.453852 0.045 Uiso 1 1 calc R U . . .
C1 C 0.5326(11) 0.10803(13) 0.3963(3) 0.0560(10) Uani 1 1 d . . . . .
H1 H 0.526161 0.074119 0.397448 0.067 Uiso 1 1 calc R U . . .
C19 C 0.0459(9) 0.44856(14) 0.5393(2) 0.0441(9) Uani 1 1 d . . . . .
H19 H 0.044773 0.482385 0.534595 0.053 Uiso 1 1 calc R U . . .
C3 C 0.6596(11) 0.18184(14) 0.3343(3) 0.0568(12) Uani 1 1 d . . . . .
H3 H 0.741670 0.197917 0.292131 0.068 Uiso 1 1 calc R U . . .
C2 C 0.6561(12) 0.13163(15) 0.3358(3) 0.0677(14) Uani 1 1 d . . . . .
H2 H 0.738410 0.113964 0.295412 0.081 Uiso 1 1 calc R U . . .
O1 O 0.0371(8) 0.21855(13) 0.1896(2) 0.0746(10) Uani 1 1 d D . . . .
H1A H -0.116(9) 0.233(2) 0.171(4) 0.112 Uiso 1 1 d D U . . .
H1B H 0.184(9) 0.231(2) 0.172(4) 0.112 Uiso 1 1 d D U . . .
O2 O 0.5154(18) 0.49668(13) 0.8972(2) 0.137(2) Uani 1 1 d D . . . .
H2C H 0.52(3) 0.483(4) 0.850(3) 0.206 Uiso 1 1 d D U . . .
H2D H 0.46(3) 0.477(3) 0.933(5) 0.206 Uiso 1 1 d D 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
N1 C8 1.339(4) . ?
N1 C9 1.345(4) . ?
N2 C14 1.331(4) . ?
N2 C13 1.334(5) . ?
N2 H2A 0.8600 . ?
N4 C1 1.326(5) . ?
N4 C5 1.332(5) . ?
N4 H4A 0.8600 . ?
N3 C19 1.322(5) . ?
N3 C18 1.328(5) . ?
N3 H3A 0.8600 . ?
C11 C15 1.388(4) . ?
C11 C12 1.401(4) . ?
C11 C8 1.491(4) . ?
C8 C7 1.388(5) . ?
C15 C14 1.369(5) . ?
C15 H15 0.9300 . ?
C14 H14 0.9300 . ?
C18 C17 1.365(5) . ?
C18 H18 0.9300 . ?
C9 C10 1.386(4) . ?
C9 C16 1.490(4) . ?
C10 C6 1.395(5) . ?
C10 H10 0.9300 . ?
C16 C20 1.385(5) . ?
C16 C17 1.396(4) . ?
C17 H17 0.9300 . ?
C13 C12 1.362(5) . ?
C13 H13 0.9300 . ?
C6 C7 1.392(5) . ?
C6 C4 1.487(4) . ?
C7 H7 0.9300 . ?
C12 H12 0.9300 . ?
C5 C4 1.376(5) . ?
C5 H5 0.9300 . ?
C4 C3 1.393(5) . ?
C20 C19 1.379(5) . ?
C20 H20 0.9300 . ?
C1 C2 1.353(6) . ?
C1 H1 0.9300 . ?
C19 H19 0.9300 . ?
C3 C2 1.376(6) . ?
C3 H3 0.9300 . ?
C2 H2 0.9300 . ?
O1 H1A 0.86(3) . ?
O1 H1B 0.84(3) . ?
O2 H2C 0.85(3) . ?
O2 H2D 0.85(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 N1 C9 118.4(3) . . ?
C14 N2 C13 122.2(3) . . ?
C14 N2 H2A 118.9 . . ?
C13 N2 H2A 118.9 . . ?
C1 N4 C5 123.5(3) . . ?
C1 N4 H4A 118.2 . . ?
C5 N4 H4A 118.2 . . ?
C19 N3 C18 122.2(3) . . ?
C19 N3 H3A 118.9 . . ?
C18 N3 H3A 118.9 . . ?
C15 C11 C12 117.8(3) . . ?
C15 C11 C8 119.7(3) . . ?
C12 C11 C8 122.5(3) . . ?
N1 C8 C7 122.5(3) . . ?
N1 C8 C11 115.5(3) . . ?
C7 C8 C11 122.0(3) . . ?
C14 C15 C11 120.0(3) . . ?
C14 C15 H15 120.0 . . ?
C11 C15 H15 120.0 . . ?
N2 C14 C15 120.0(3) . . ?
N2 C14 H14 120.0 . . ?
C15 C14 H14 120.0 . . ?
N3 C18 C17 120.5(3) . . ?
N3 C18 H18 119.7 . . ?
C17 C18 H18 119.7 . . ?
N1 C9 C10 122.2(3) . . ?
N1 C9 C16 115.3(3) . . ?
C10 C9 C16 122.5(3) . . ?
C9 C10 C6 119.8(3) . . ?
C9 C10 H10 120.1 . . ?
C6 C10 H10 120.1 . . ?
C20 C16 C17 118.4(3) . . ?
C20 C16 C9 120.0(3) . . ?
C17 C16 C9 121.6(3) . . ?
C18 C17 C16 119.3(3) . . ?
C18 C17 H17 120.3 . . ?
C16 C17 H17 120.3 . . ?
N2 C13 C12 120.1(3) . . ?
N2 C13 H13 120.0 . . ?
C12 C13 H13 120.0 . . ?
C7 C6 C10 117.4(3) . . ?
C7 C6 C4 121.1(3) . . ?
C10 C6 C4 121.6(3) . . ?
C8 C7 C6 119.7(3) . . ?
C8 C7 H7 120.1 . . ?
C6 C7 H7 120.1 . . ?
C13 C12 C11 119.9(3) . . ?
C13 C12 H12 120.1 . . ?
C11 C12 H12 120.1 . . ?
N4 C5 C4 120.5(3) . . ?
N4 C5 H5 119.7 . . ?
C4 C5 H5 119.7 . . ?
C5 C4 C3 116.5(3) . . ?
C5 C4 C6 121.2(3) . . ?
C3 C4 C6 122.3(3) . . ?
C19 C20 C16 119.4(3) . . ?
C19 C20 H20 120.3 . . ?
C16 C20 H20 120.3 . . ?
N4 C1 C2 118.8(4) . . ?
N4 C1 H1 120.6 . . ?
C2 C1 H1 120.6 . . ?
N3 C19 C20 120.2(3) . . ?
N3 C19 H19 119.9 . . ?
C20 C19 H19 119.9 . . ?
C2 C3 C4 120.9(4) . . ?
C2 C3 H3 119.6 . . ?
C4 C3 H3 119.6 . . ?
C1 C2 C3 119.8(4) . . ?
C1 C2 H2 120.1 . . ?
C3 C2 H2 120.1 . . ?
H1A O1 H1B 111(5) . . ?
H2C O2 H2D 111(7) . . ?

_refine_diff_density_max         0.230
_refine_diff_density_min         -0.196
_refine_diff_density_rms         0.035

####################################################################### 
# 
# 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_shelx_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 2012318'
_audit_update_record             
;
2020-06-25 deposited with the CCDC.	2021-04-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H19 Cl3 N4 O13'
_chemical_formula_weight         629.74

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                   7.9128(5)
_cell_length_b                   12.1194(7)
_cell_length_c                   14.6144(9)
_cell_angle_alpha                111.868(3)
_cell_angle_beta                 97.267(3)
_cell_angle_gamma                95.940(3)
_cell_volume                     1272.82(14)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3120
_cell_measurement_theta_min      1.5
_cell_measurement_theta_max      25.0

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.643
_exptl_crystal_F_000             644
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.07
_exptl_absorpt_coefficient_mu    0.436
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.944
_exptl_absorpt_correction_T_max  0.970
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker SMART APEX II CCD area-detector'
_diffrn_measurement_method       'ω and φ'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13693
_diffrn_reflns_av_unetI/netI     0.0269
_diffrn_reflns_av_R_equivalents  0.0289
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.526
_diffrn_reflns_theta_max         25.073
_diffrn_reflns_theta_full        25.073
_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             4470
_reflns_number_gt                3873
_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       'APEX2 (Bruker, 2007)'
_computing_cell_refinement       'APEX2(Bruker,2007)and SAINT (Bruker,2007)'
_computing_data_reduction        'SAINT(Bruker,2007)and XPREP(Bruker,2007)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    
;    
ORTEP-3 for Windows (Farrugia, 1997), DIAMOND (Brandenburg,
1999) and Mercury (Macrae et al., 2006)
;
_computing_publication_material  'PLATON (Spek, 2009)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1356P)²+2.2152P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2018/1 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.013(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4470
_refine_ls_number_parameters     362
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0810
_refine_ls_R_factor_gt           0.0740
_refine_ls_wR_factor_ref         0.2272
_refine_ls_wR_factor_gt          0.2187
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_restrained_S_all      1.064
_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
Cl1 Cl 0.65912(12) 0.13626(8) 0.30549(7) 0.0384(3) Uani 1 1 d . . . . .
Cl2 Cl 0.10918(15) 0.92634(10) 0.30675(10) 0.0550(4) Uani 1 1 d . . . . .
Cl3 Cl 0.2821(2) 0.66553(13) 0.96674(10) 0.0713(5) Uani 1 1 d . . . . .
O3 O 0.5791(4) 0.0245(3) 0.2257(2) 0.0516(8) Uani 1 1 d . . . . .
O4 O 0.7170(4) 0.1138(3) 0.3938(2) 0.0520(8) Uani 1 1 d . . . . .
N1 N 0.3032(4) 0.5156(3) 0.3982(2) 0.0311(7) Uani 1 1 d . . . . .
O2 O 0.8039(4) 0.1872(3) 0.2773(3) 0.0646(10) Uani 1 1 d . . . . .
O5 O 0.5376(5) 0.2182(3) 0.3281(3) 0.0635(10) Uani 1 1 d . . . . .
N2 N 0.6032(5) 0.8637(3) 0.3542(3) 0.0471(9) Uani 1 1 d . . . . .
H2A H 0.655425 0.933571 0.362653 0.057 Uiso 1 1 calc R U . . .
C9 C 0.2247(4) 0.4092(3) 0.3918(3) 0.0288(7) Uani 1 1 d . . . . .
N3 N 0.0880(5) 0.4090(3) 0.6618(3) 0.0478(9) Uani 1 1 d . . . . .
H3A H 0.061064 0.409021 0.716938 0.057 Uiso 1 1 calc R U . . .
C16 C 0.1747(5) 0.4080(3) 0.4865(3) 0.0306(7) Uani 1 1 d . . . . .
C8 C 0.3513(5) 0.5220(3) 0.3158(3) 0.0319(8) Uani 1 1 d . . . . .
N4 N 0.2495(5) -0.0047(3) 0.0546(3) 0.0521(9) Uani 1 1 d . . . . .
H4A H 0.264696 -0.070351 0.061920 0.062 Uiso 1 1 calc R U . . .
C4 C 0.2325(5) 0.2024(3) 0.1274(3) 0.0365(8) Uani 1 1 d . . . . .
C6 C 0.2477(5) 0.3122(3) 0.2195(3) 0.0326(8) Uani 1 1 d . . . . .
C7 C 0.3260(5) 0.4230(3) 0.2251(3) 0.0359(8) Uani 1 1 d . . . . .
H7 H 0.360905 0.430905 0.169092 0.043 Uiso 1 1 calc R U . . .
C10 C 0.1942(5) 0.3063(3) 0.3046(3) 0.0319(8) Uani 1 1 d . . . . .
H10 H 0.138605 0.234050 0.303108 0.038 Uiso 1 1 calc R U . . .
C11 C 0.4397(5) 0.6427(3) 0.3277(3) 0.0335(8) Uani 1 1 d . . . . .
C17 C 0.0767(5) 0.3075(3) 0.4894(3) 0.0393(9) Uani 1 1 d . . . . .
H17 H 0.039927 0.238511 0.431155 0.047 Uiso 1 1 calc R U . . .
C20 C 0.2264(5) 0.5088(3) 0.5753(3) 0.0394(9) Uani 1 1 d . . . . .
H20 H 0.291553 0.577364 0.575439 0.047 Uiso 1 1 calc R U . . .
C5 C 0.2544(5) 0.0945(3) 0.1358(3) 0.0417(9) Uani 1 1 d . . . . .
H5 H 0.272651 0.091303 0.198802 0.050 Uiso 1 1 calc R U . . .
O8 O 0.2116(6) 0.8858(5) 0.3683(4) 0.0999(16) Uani 1 1 d . . . . .
C15 C 0.4958(5) 0.7312(3) 0.4232(3) 0.0391(9) Uani 1 1 d . . . . .
H15 H 0.477568 0.715817 0.479274 0.047 Uiso 1 1 calc R U . . .
C18 C 0.0349(6) 0.3103(4) 0.5777(3) 0.0479(10) Uani 1 1 d . . . . .
H18 H -0.030908 0.243304 0.579593 0.057 Uiso 1 1 calc R U . . .
C12 C 0.4688(6) 0.6694(4) 0.2469(3) 0.0466(10) Uani 1 1 d . . . . .
H12 H 0.433229 0.611327 0.182185 0.056 Uiso 1 1 calc R U . . .
C19 C 0.1820(6) 0.5079(4) 0.6625(3) 0.0464(10) Uani 1 1 d . . . . .
H19 H 0.216854 0.575571 0.721960 0.056 Uiso 1 1 calc R U . . .
C14 C 0.5785(6) 0.8420(4) 0.4339(3) 0.0463(10) Uani 1 1 d . . . . .
H14 H 0.617233 0.901799 0.497614 0.056 Uiso 1 1 calc R U . . .
C3 C 0.2032(6) 0.2017(4) 0.0316(3) 0.0484(10) Uani 1 1 d . . . . .
H3 H 0.187762 0.272459 0.022892 0.058 Uiso 1 1 calc R U . . .
O7 O 0.1570(9) 1.0476(4) 0.3297(4) 0.1114(19) Uani 1 1 d . . . . .
C13 C 0.5510(6) 0.7827(4) 0.2620(4) 0.0523(11) Uani 1 1 d . . . . .
H13 H 0.569347 0.801626 0.207613 0.063 Uiso 1 1 calc R U . . .
C1 C 0.2218(6) -0.0058(5) -0.0382(3) 0.0590(13) Uani 1 1 d . . . . .
H1 H 0.219840 -0.076513 -0.093400 0.071 Uiso 1 1 calc R U . . .
O6 O 0.1558(8) 0.8655(5) 0.2061(4) 0.1113(18) Uani 1 1 d . . . . .
C2 C 0.1968(7) 0.0967(5) -0.0508(3) 0.0597(13) Uani 1 1 d . . . . .
H2 H 0.175357 0.096365 -0.114960 0.072 Uiso 1 1 calc R U . . .
O9 O -0.0634(6) 0.8853(6) 0.2920(5) 0.124(2) Uani 1 1 d . . . . .
O12 O 0.3682(11) 0.7708(6) 1.0427(5) 0.146(3) Uani 1 1 d . . . . .
O10 O 0.3691(10) 0.5915(7) 0.9010(6) 0.163(3) Uani 1 1 d . . . . .
O13 O 0.1900(12) 0.5952(7) 1.0072(5) 0.178(4) Uani 1 1 d . . . . .
O11 O 0.1532(12) 0.6924(9) 0.9049(7) 0.191(4) Uani 1 1 d . . . . .
O1 O 0.9792(8) 0.3939(4) 0.8238(3) 0.1074(19) Uani 1 1 d . . . . .
H1A H 0.901110 0.343217 0.828067 0.161 Uiso 1 1 d . U . . .
H1B H 0.968500 0.445400 0.861200 0.161 Uiso 1 1 d . 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
Cl1 O2 1.423(3) . ?
Cl1 O3 1.433(3) . ?
Cl1 O5 1.433(3) . ?
Cl1 O4 1.445(3) . ?
Cl2 O9 1.365(5) . ?
Cl2 O7 1.379(4) . ?
Cl2 O8 1.391(4) . ?
Cl2 O6 1.492(5) . ?
Cl3 O10 1.362(6) . ?
Cl3 O12 1.378(6) . ?
Cl3 O13 1.402(6) . ?
Cl3 O11 1.421(8) . ?
N1 C8 1.334(5) . ?
N1 C9 1.337(4) . ?
N2 C13 1.319(6) . ?
N2 C14 1.320(6) . ?
N2 H2A 0.8600 . ?
C9 C10 1.383(5) . ?
C9 C16 1.493(5) . ?
N3 C18 1.337(6) . ?
N3 C19 1.339(6) . ?
N3 H3A 0.8600 . ?
C16 C20 1.387(5) . ?
C16 C17 1.392(5) . ?
C8 C7 1.391(5) . ?
C8 C11 1.493(5) . ?
N4 C5 1.331(5) . ?
N4 C1 1.340(6) . ?
N4 H4A 0.8600 . ?
C4 C5 1.384(6) . ?
C4 C3 1.387(6) . ?
C4 C6 1.479(5) . ?
C6 C10 1.387(5) . ?
C6 C7 1.388(5) . ?
C7 H7 0.9300 . ?
C10 H10 0.9300 . ?
C11 C12 1.374(5) . ?
C11 C15 1.388(5) . ?
C17 C18 1.361(6) . ?
C17 H17 0.9300 . ?
C20 C19 1.369(6) . ?
C20 H20 0.9300 . ?
C5 H5 0.9300 . ?
C15 C14 1.375(6) . ?
C15 H15 0.9300 . ?
C18 H18 0.9300 . ?
C12 C13 1.382(6) . ?
C12 H12 0.9300 . ?
C19 H19 0.9300 . ?
C14 H14 0.9300 . ?
C3 C2 1.380(7) . ?
C3 H3 0.9300 . ?
C13 H13 0.9300 . ?
C1 C2 1.352(8) . ?
C1 H1 0.9300 . ?
C2 H2 0.9300 . ?
O1 H1A 0.8499 . ?
O1 H1B 0.6810 . ?

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
O2 Cl1 O3 109.5(2) . . ?
O2 Cl1 O5 110.2(2) . . ?
O3 Cl1 O5 110.18(19) . . ?
O2 Cl1 O4 109.1(2) . . ?
O3 Cl1 O4 109.08(19) . . ?
O5 Cl1 O4 108.7(2) . . ?
O9 Cl2 O7 116.6(4) . . ?
O9 Cl2 O8 114.2(3) . . ?
O7 Cl2 O8 112.3(4) . . ?
O9 Cl2 O6 103.6(4) . . ?
O7 Cl2 O6 104.4(3) . . ?
O8 Cl2 O6 103.8(4) . . ?
O10 Cl3 O12 120.6(5) . . ?
O10 Cl3 O13 107.0(5) . . ?
O12 Cl3 O13 109.6(4) . . ?
O10 Cl3 O11 104.2(6) . . ?
O12 Cl3 O11 109.6(5) . . ?
O13 Cl3 O11 104.6(7) . . ?
C8 N1 C9 117.8(3) . . ?
C13 N2 C14 122.7(4) . . ?
C13 N2 H2A 118.7 . . ?
C14 N2 H2A 118.7 . . ?
N1 C9 C10 123.0(3) . . ?
N1 C9 C16 115.2(3) . . ?
C10 C9 C16 121.8(3) . . ?
C18 N3 C19 121.9(3) . . ?
C18 N3 H3A 119.0 . . ?
C19 N3 H3A 119.0 . . ?
C20 C16 C17 118.0(3) . . ?
C20 C16 C9 120.0(3) . . ?
C17 C16 C9 121.9(3) . . ?
N1 C8 C7 123.0(3) . . ?
N1 C8 C11 115.4(3) . . ?
C7 C8 C11 121.5(3) . . ?
C5 N4 C1 122.3(4) . . ?
C5 N4 H4A 118.8 . . ?
C1 N4 H4A 118.8 . . ?
C5 C4 C3 117.3(4) . . ?
C5 C4 C6 119.2(3) . . ?
C3 C4 C6 123.5(4) . . ?
C10 C6 C7 118.1(3) . . ?
C10 C6 C4 121.1(3) . . ?
C7 C6 C4 120.7(3) . . ?
C6 C7 C8 118.9(3) . . ?
C6 C7 H7 120.6 . . ?
C8 C7 H7 120.6 . . ?
C9 C10 C6 119.2(3) . . ?
C9 C10 H10 120.4 . . ?
C6 C10 H10 120.4 . . ?
C12 C11 C15 118.5(3) . . ?
C12 C11 C8 122.2(3) . . ?
C15 C11 C8 119.3(3) . . ?
C18 C17 C16 119.8(4) . . ?
C18 C17 H17 120.1 . . ?
C16 C17 H17 120.1 . . ?
C19 C20 C16 120.3(4) . . ?
C19 C20 H20 119.9 . . ?
C16 C20 H20 119.9 . . ?
N4 C5 C4 120.7(4) . . ?
N4 C5 H5 119.7 . . ?
C4 C5 H5 119.7 . . ?
C14 C15 C11 119.2(4) . . ?
C14 C15 H15 120.4 . . ?
C11 C15 H15 120.4 . . ?
N3 C18 C17 120.3(4) . . ?
N3 C18 H18 119.8 . . ?
C17 C18 H18 119.8 . . ?
C11 C12 C13 119.9(4) . . ?
C11 C12 H12 120.1 . . ?
C13 C12 H12 120.1 . . ?
N3 C19 C20 119.6(4) . . ?
N3 C19 H19 120.2 . . ?
C20 C19 H19 120.2 . . ?
N2 C14 C15 120.2(4) . . ?
N2 C14 H14 119.9 . . ?
C15 C14 H14 119.9 . . ?
C2 C3 C4 120.3(4) . . ?
C2 C3 H3 119.8 . . ?
C4 C3 H3 119.8 . . ?
N2 C13 C12 119.5(4) . . ?
N2 C13 H13 120.2 . . ?
C12 C13 H13 120.2 . . ?
N4 C1 C2 119.5(4) . . ?
N4 C1 H1 120.3 . . ?
C2 C1 H1 120.3 . . ?
C1 C2 C3 119.9(4) . . ?
C1 C2 H2 120.0 . . ?
C3 C2 H2 120.0 . . ?
H1A O1 H1B 100.8 . . ?

_refine_diff_density_max         1.349
_refine_diff_density_min         -0.941
_refine_diff_density_rms         0.099

