# Supplementary Information (SI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_bq057
_database_code_depnum_ccdc_archive 'CCDC 2361243'
loop_
_audit_author_name
_audit_author_address
'Eric Hosten'
;Nelson Mandela University
South Africa
;
_audit_update_record             
;
2024-08-02 deposited with the CCDC.	2024-08-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            
N,N-bis(9-phenyl-9H-xanthen-9-yl)butane-1,4-diamine
_chemical_temperature_decomposition 329.75
_chemical_formula_moiety         'C42 H36 N2 O2, 1.5(C6 H4 Cl2)'
_chemical_formula_sum            'C51 H42 Cl3 N2 O2'
_chemical_formula_weight         821.21

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

_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                   8.8318(4)
_cell_length_b                   14.6939(6)
_cell_length_c                   16.5191(7)
_cell_angle_alpha                85.3830(15)
_cell_angle_beta                 83.1590(16)
_cell_angle_gamma                77.5052(14)
_cell_volume                     2074.76(15)
_cell_formula_units_Z            2
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    9480
_cell_measurement_theta_min      2.50
_cell_measurement_theta_max      28.18

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.315
_exptl_crystal_F_000             858
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.394
_exptl_crystal_size_mid          0.355
_exptl_crystal_size_min          0.328
_exptl_absorpt_coefficient_mu    0.265
_shelx_estimated_absorpt_T_min   0.903
_shelx_estimated_absorpt_T_max   0.918
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.9153
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'SADABS V2016/2 (Krause, 2015)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      200(2)
_diffrn_source                   'sealed x-ray tube'
_diffrn_source_power             70
_diffrn_source_voltage           50
_diffrn_source_current           1.4
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker D8 QUEST'
_diffrn_measurement_device       'four-circle KAPPA diffractometer'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector                 'Bruker PHOTON II 7 detector'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            170208
_diffrn_reflns_av_unetI/netI     0.0274
_diffrn_reflns_av_R_equivalents  0.0498
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.941
_diffrn_reflns_theta_max         28.295
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             10290
_reflns_number_gt                7352
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker Instrument Service V6.2.16'
_computing_cell_refinement       'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_data_reduction        'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2015a)'
_computing_structure_refinement  
'SHELXL-2019/2 (Sheldrick, 2015b)  and ShelXle (Hübschle, 2011)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 2012)'
_computing_publication_material  
'PLATON (Spek, 2009) and MERCURY (Macrae, 2008)'

_refine_special_details          
;All non-hydrogen atoms were refined anisotropically. Carbon-bound H atoms were
placed in calculated positions and were included in the refinement in the riding
model approximation, with Uiso(H) set to 1.2 Ueq(C).

The nitrogen-bound H atoms were located on a difference map and refined freely.

The dichlorobenzene solvent molecule C81 > C86, Cl81, Cl82 is disordered around
an inversion center necessitating the use of SAME and SIMU.

A reflection with large difference between its observed and calculated
intensities was omitted. This is due to obstruction by the beam stop.,disorder
;


_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0646P)²+1.7610P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_extinction_coef       0.0102(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         10290
_refine_ls_number_parameters     568
_refine_ls_number_restraints     66
_refine_ls_R_factor_all          0.0927
_refine_ls_R_factor_gt           0.0576
_refine_ls_wR_factor_ref         0.1807
_refine_ls_wR_factor_gt          0.1372
_refine_ls_goodness_of_fit_ref   1.112
_refine_ls_restrained_S_all      1.115
_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 0.34692(17) 0.15407(12) 0.25705(9) 0.0424(4) Uani 1 1 d . . . . .
O2 O 0.09097(17) 0.93760(11) 0.24676(9) 0.0385(3) Uani 1 1 d . . . . .
N1 N 0.4411(2) 0.35111(11) 0.37428(10) 0.0327(4) Uani 1 1 d . . . . .
N2 N 0.0970(2) 0.68288(11) 0.16188(11) 0.0350(4) Uani 1 1 d . . . . .
C1 C 0.4738(2) 0.24788(12) 0.37716(11) 0.0261(3) Uani 1 1 d . . . . .
C2 C 0.3661(3) 0.39559(14) 0.30227(13) 0.0407(5) Uani 1 1 d . . . . .
H2A H 0.279787 0.365112 0.294318 0.049 Uiso 1 1 calc R U . . .
H2B H 0.442896 0.386572 0.253275 0.049 Uiso 1 1 calc R U . . .
C3 C 0.3027(3) 0.49900(14) 0.31104(13) 0.0377(4) Uani 1 1 d . . . . .
H3A H 0.387438 0.529011 0.322423 0.045 Uiso 1 1 calc R U . . .
H3B H 0.220627 0.508124 0.357760 0.045 Uiso 1 1 calc R U . . .
C4 C 0.2349(3) 0.54489(14) 0.23373(13) 0.0402(5) Uani 1 1 d . . . . .
H4A H 0.317582 0.534536 0.187381 0.048 Uiso 1 1 calc R U . . .
H4B H 0.151193 0.513808 0.222662 0.048 Uiso 1 1 calc R U . . .
C5 C 0.1690(3) 0.64845(14) 0.23732(13) 0.0398(5) Uani 1 1 d . . . . .
H5A H 0.090069 0.660508 0.285177 0.048 Uiso 1 1 calc R U . . .
H5B H 0.253279 0.681514 0.243102 0.048 Uiso 1 1 calc R U . . .
C6 C 0.0514(2) 0.78508(12) 0.15023(11) 0.0286(4) Uani 1 1 d . . . . .
C11 C 0.3185(2) 0.21685(12) 0.39074(11) 0.0270(4) Uani 1 1 d . . . . .
C12 C 0.2654(2) 0.17275(14) 0.33227(12) 0.0317(4) Uani 1 1 d . . . . .
C13 C 0.1238(2) 0.14358(16) 0.34579(14) 0.0400(5) Uani 1 1 d . . . . .
H13 H 0.089763 0.113412 0.304676 0.048 Uiso 1 1 calc R U . . .
C14 C 0.0339(2) 0.15900(17) 0.41934(15) 0.0443(5) Uani 1 1 d . . . . .
H14 H -0.062722 0.139471 0.429094 0.053 Uiso 1 1 calc R U . . .
C15 C 0.0839(2) 0.20290(17) 0.47915(14) 0.0430(5) Uani 1 1 d . . . . .
H15 H 0.021916 0.213259 0.529966 0.052 Uiso 1 1 calc R U . . .
C16 C 0.2243(2) 0.23161(15) 0.46472(12) 0.0355(4) Uani 1 1 d . . . . .
H16 H 0.257488 0.262010 0.505956 0.043 Uiso 1 1 calc R U . . .
C21 C 0.5653(2) 0.20813(13) 0.29907(11) 0.0290(4) Uani 1 1 d . . . . .
C22 C 0.4982(2) 0.16736(14) 0.24393(12) 0.0328(4) Uani 1 1 d . . . . .
C23 C 0.5803(3) 0.13561(16) 0.17018(13) 0.0419(5) Uani 1 1 d . . . . .
H23 H 0.531483 0.107825 0.133317 0.050 Uiso 1 1 calc R U . . .
C24 C 0.7322(3) 0.14506(17) 0.15168(14) 0.0453(5) Uani 1 1 d . . . . .
H24 H 0.788700 0.124116 0.101664 0.054 Uiso 1 1 calc R U . . .
C25 C 0.8028(3) 0.18508(18) 0.20590(14) 0.0458(5) Uani 1 1 d . . . . .
H25 H 0.908073 0.191206 0.193389 0.055 Uiso 1 1 calc R U . . .
C26 C 0.7198(2) 0.21617(16) 0.27837(13) 0.0386(5) Uani 1 1 d . . . . .
H26 H 0.769423 0.243739 0.315044 0.046 Uiso 1 1 calc R U . . .
C31 C 0.5656(2) 0.20878(14) 0.45027(11) 0.0296(4) Uani 1 1 d . . . . .
C32 C 0.6085(2) 0.26392(17) 0.50365(13) 0.0398(5) Uani 1 1 d . . . . .
H32 H 0.584385 0.329997 0.495545 0.048 Uiso 1 1 calc R U . . .
C33 C 0.6885(3) 0.2213(2) 0.57028(14) 0.0527(6) Uani 1 1 d . . . . .
H33 H 0.717646 0.259079 0.607256 0.063 Uiso 1 1 calc R U . . .
C34 C 0.7247(3) 0.1260(2) 0.58254(14) 0.0552(7) Uani 1 1 d . . . . .
H34 H 0.778840 0.098253 0.627672 0.066 Uiso 1 1 calc R U . . .
C35 C 0.6826(3) 0.07069(19) 0.52937(15) 0.0495(6) Uani 1 1 d . . . . .
H35 H 0.707816 0.004626 0.537506 0.059 Uiso 1 1 calc R U . . .
C36 C 0.6031(2) 0.11198(15) 0.46387(13) 0.0382(5) Uani 1 1 d . . . . .
H36 H 0.573579 0.073569 0.427520 0.046 Uiso 1 1 calc R U . . .
C41 C -0.0626(2) 0.82685(14) 0.22064(11) 0.0309(4) Uani 1 1 d . . . . .
C42 C -0.0390(2) 0.89875(14) 0.26316(11) 0.0318(4) Uani 1 1 d . . . . .
C43 C -0.1464(3) 0.93662(17) 0.32652(14) 0.0452(5) Uani 1 1 d . . . . .
H43 H -0.127944 0.985972 0.355245 0.054 Uiso 1 1 calc R U . . .
C44 C -0.2798(3) 0.90205(19) 0.34733(15) 0.0509(6) Uani 1 1 d . . . . .
H44 H -0.353182 0.927431 0.390795 0.061 Uiso 1 1 calc R U . . .
C45 C -0.3073(3) 0.83074(19) 0.30539(16) 0.0512(6) Uani 1 1 d . . . . .
H45 H -0.399622 0.807178 0.319565 0.061 Uiso 1 1 calc R U . . .
C46 C -0.1994(3) 0.79393(17) 0.24256(14) 0.0435(5) Uani 1 1 d . . . . .
H46 H -0.218869 0.745043 0.213611 0.052 Uiso 1 1 calc R U . . .
C51 C 0.1966(2) 0.82641(13) 0.14278(11) 0.0300(4) Uani 1 1 d . . . . .
C52 C 0.2105(2) 0.89645(13) 0.19086(11) 0.0307(4) Uani 1 1 d . . . . .
C53 C 0.3460(3) 0.93073(16) 0.18618(13) 0.0399(5) Uani 1 1 d . . . . .
H53 H 0.353099 0.977874 0.220835 0.048 Uiso 1 1 calc R U . . .
C54 C 0.4701(3) 0.89578(18) 0.13088(16) 0.0484(6) Uani 1 1 d . . . . .
H54 H 0.563197 0.919051 0.127059 0.058 Uiso 1 1 calc R U . . .
C55 C 0.4596(3) 0.8267(2) 0.08078(17) 0.0533(6) Uani 1 1 d . . . . .
H55 H 0.544947 0.802918 0.042301 0.064 Uiso 1 1 calc R U . . .
C56 C 0.3244(3) 0.79254(17) 0.08693(15) 0.0448(5) Uani 1 1 d . . . . .
H56 H 0.318201 0.745010 0.052480 0.054 Uiso 1 1 calc R U . . .
C61 C -0.0286(2) 0.80938(14) 0.07101(11) 0.0307(4) Uani 1 1 d . . . . .
C62 C -0.0462(3) 0.74284(16) 0.02045(13) 0.0423(5) Uani 1 1 d . . . . .
H62 H -0.006606 0.678587 0.033518 0.051 Uiso 1 1 calc R U . . .
C63 C -0.1222(3) 0.76974(18) -0.04997(14) 0.0480(6) Uani 1 1 d . . . . .
H63 H -0.133650 0.723495 -0.084465 0.058 Uiso 1 1 calc R U . . .
C64 C -0.1804(3) 0.86219(18) -0.06976(13) 0.0432(5) Uani 1 1 d . . . . .
H64 H -0.231071 0.879902 -0.117924 0.052 Uiso 1 1 calc R U . . .
C65 C -0.1648(3) 0.92897(18) -0.01952(15) 0.0475(5) Uani 1 1 d . . . . .
H65 H -0.205999 0.993060 -0.032440 0.057 Uiso 1 1 calc R U . . .
C66 C -0.0886(3) 0.90245(16) 0.05035(14) 0.0435(5) Uani 1 1 d . . . . .
H66 H -0.077537 0.949041 0.084571 0.052 Uiso 1 1 calc R U . . .
Cl71 Cl 0.92905(11) 0.40039(7) 0.20106(6) 0.0851(3) Uani 1 1 d D . . . .
Cl72 Cl 0.65975(12) 0.58273(6) 0.20674(5) 0.0777(3) Uani 1 1 d D . . . .
C71 C 0.8561(3) 0.45124(19) 0.29192(17) 0.0542(6) Uani 1 1 d D . . . .
C72 C 0.7396(3) 0.53185(18) 0.29378(16) 0.0505(6) Uani 1 1 d D . . . .
C73 C 0.6856(3) 0.57126(19) 0.36781(17) 0.0570(6) Uani 1 1 d D . . . .
H73 H 0.606421 0.626519 0.369788 0.068 Uiso 1 1 calc R U . . .
C74 C 0.7456(4) 0.5311(2) 0.43893(18) 0.0605(7) Uani 1 1 d D . . . .
H74 H 0.708167 0.558850 0.489455 0.073 Uiso 1 1 calc R U . . .
C75 C 0.8598(4) 0.4508(2) 0.43622(19) 0.0634(7) Uani 1 1 d D . . . .
H75 H 0.900389 0.422564 0.485075 0.076 Uiso 1 1 calc R U . . .
C76 C 0.9153(3) 0.4114(2) 0.3629(2) 0.0636(7) Uani 1 1 d D . . . .
H76 H 0.995006 0.356318 0.361198 0.076 Uiso 1 1 calc R U . . .
H1 H 0.533(3) 0.3677(18) 0.3726(15) 0.042(7) Uiso 1 1 d . . . . .
H2 H 0.015(5) 0.659(3) 0.159(2) 0.095(13) Uiso 1 1 d . . . . .
Cl81 Cl 0.4774(4) 0.35549(17) 0.08043(15) 0.1025(10) Uani 0.5 1 d D U P A -1
Cl82 Cl 0.1899(3) 0.48643(14) 0.00522(13) 0.0902(6) Uani 0.5 1 d D U P A -1
C81 C 0.4988(10) 0.4575(4) 0.0249(3) 0.0744(17) Uani 0.5 1 d D U P A -1
C82 C 0.3711(19) 0.5143(16) -0.009(2) 0.077(3) Uani 0.5 1 d D U P A -1
C83 C 0.3839(10) 0.5995(5) -0.0579(4) 0.0781(18) Uani 0.5 1 d D U P A -1
H83 H 0.302838 0.639232 -0.084719 0.094 Uiso 0.5 1 calc R U P A -1
C84 C 0.5403(14) 0.6130(8) -0.0590(7) 0.101(3) Uani 0.5 1 d D U P A -1
H84 H 0.557990 0.668921 -0.087939 0.121 Uiso 0.5 1 calc R U P A -1
C85 C 0.6642(11) 0.5626(6) -0.0273(5) 0.095(2) Uani 0.5 1 d D U P A -1
H85 H 0.762035 0.580732 -0.033154 0.114 Uiso 0.5 1 calc R U P A -1
C86 C 0.640(2) 0.4819(17) 0.015(2) 0.086(3) Uani 0.5 1 d D U P A -1
H86 H 0.725372 0.441337 0.037398 0.103 Uiso 0.5 1 calc R U P A -1


_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 C12 1.376(2) . ?
O1 C22 1.381(2) . ?
O2 C42 1.379(2) . ?
O2 C52 1.384(2) . ?
N1 C2 1.468(3) . ?
N1 C1 1.479(2) . ?
N1 H1 0.89(3) . ?
N2 C5 1.470(3) . ?
N2 C6 1.471(2) . ?
N2 H2 0.87(4) . ?
C1 C11 1.523(2) . ?
C1 C21 1.525(2) . ?
C1 C31 1.538(2) . ?
C2 C3 1.514(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.521(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.510(3) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C41 1.520(3) . ?
C6 C51 1.522(3) . ?
C6 C61 1.541(3) . ?
C11 C12 1.383(3) . ?
C11 C16 1.398(3) . ?
C12 C13 1.396(3) . ?
C13 C14 1.376(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.385(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.383(3) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C21 C22 1.382(3) . ?
C21 C26 1.395(3) . ?
C22 C23 1.401(3) . ?
C23 C24 1.374(3) . ?
C23 H23 0.9500 . ?
C24 C25 1.383(4) . ?
C24 H24 0.9500 . ?
C25 C26 1.383(3) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
C31 C32 1.380(3) . ?
C31 C36 1.395(3) . ?
C32 C33 1.409(3) . ?
C32 H32 0.9500 . ?
C33 C34 1.370(4) . ?
C33 H33 0.9500 . ?
C34 C35 1.377(4) . ?
C34 H34 0.9500 . ?
C35 C36 1.387(3) . ?
C35 H35 0.9500 . ?
C36 H36 0.9500 . ?
C41 C42 1.379(3) . ?
C41 C46 1.395(3) . ?
C42 C43 1.391(3) . ?
C43 C44 1.378(3) . ?
C43 H43 0.9500 . ?
C44 C45 1.380(4) . ?
C44 H44 0.9500 . ?
C45 C46 1.382(3) . ?
C45 H45 0.9500 . ?
C46 H46 0.9500 . ?
C51 C52 1.384(3) . ?
C51 C56 1.399(3) . ?
C52 C53 1.387(3) . ?
C53 C54 1.376(3) . ?
C53 H53 0.9500 . ?
C54 C55 1.385(4) . ?
C54 H54 0.9500 . ?
C55 C56 1.382(3) . ?
C55 H55 0.9500 . ?
C56 H56 0.9500 . ?
C61 C62 1.381(3) . ?
C61 C66 1.386(3) . ?
C62 C63 1.399(3) . ?
C62 H62 0.9500 . ?
C63 C64 1.372(4) . ?
C63 H63 0.9500 . ?
C64 C65 1.374(3) . ?
C64 H64 0.9500 . ?
C65 C66 1.391(3) . ?
C65 H65 0.9500 . ?
C66 H66 0.9500 . ?
Cl71 C71 1.723(3) . ?
Cl72 C72 1.721(3) . ?
C71 C76 1.376(4) . ?
C71 C72 1.391(4) . ?
C72 C73 1.383(4) . ?
C73 C74 1.382(4) . ?
C73 H73 0.9500 . ?
C74 C75 1.377(4) . ?
C74 H74 0.9500 . ?
C75 C76 1.376(4) . ?
C75 H75 0.9500 . ?
C76 H76 0.9500 . ?
Cl81 C81 1.728(6) . ?
Cl82 C82 1.720(13) . ?
C81 C86 1.359(14) . ?
C81 C82 1.394(13) . ?
C82 C83 1.455(13) . ?
C83 C84 1.435(12) . ?
C83 H83 0.9500 . ?
C84 C85 1.321(12) . ?
C84 H84 0.9500 . ?
C85 C86 1.368(13) . ?
C85 H85 0.9500 . ?
C86 H86 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C12 O1 C22 118.19(15) . . ?
C42 O2 C52 118.41(15) . . ?
C2 N1 C1 113.82(15) . . ?
C2 N1 H1 107.9(16) . . ?
C1 N1 H1 106.8(16) . . ?
C5 N2 C6 115.19(16) . . ?
C5 N2 H2 111(3) . . ?
C6 N2 H2 109(3) . . ?
N1 C1 C11 108.09(14) . . ?
N1 C1 C21 112.72(15) . . ?
C11 C1 C21 109.32(15) . . ?
N1 C1 C31 109.43(15) . . ?
C11 C1 C31 107.87(14) . . ?
C21 C1 C31 109.28(14) . . ?
N1 C2 C3 111.79(17) . . ?
N1 C2 H2A 109.3 . . ?
C3 C2 H2A 109.3 . . ?
N1 C2 H2B 109.3 . . ?
C3 C2 H2B 109.3 . . ?
H2A C2 H2B 107.9 . . ?
C2 C3 C4 110.95(17) . . ?
C2 C3 H3A 109.4 . . ?
C4 C3 H3A 109.4 . . ?
C2 C3 H3B 109.4 . . ?
C4 C3 H3B 109.4 . . ?
H3A C3 H3B 108.0 . . ?
C5 C4 C3 114.37(18) . . ?
C5 C4 H4A 108.7 . . ?
C3 C4 H4A 108.7 . . ?
C5 C4 H4B 108.7 . . ?
C3 C4 H4B 108.7 . . ?
H4A C4 H4B 107.6 . . ?
N2 C5 C4 109.05(17) . . ?
N2 C5 H5A 109.9 . . ?
C4 C5 H5A 109.9 . . ?
N2 C5 H5B 109.9 . . ?
C4 C5 H5B 109.9 . . ?
H5A C5 H5B 108.3 . . ?
N2 C6 C41 111.54(15) . . ?
N2 C6 C51 109.16(15) . . ?
C41 C6 C51 109.69(15) . . ?
N2 C6 C61 108.71(15) . . ?
C41 C6 C61 108.33(15) . . ?
C51 C6 C61 109.38(15) . . ?
C12 C11 C16 117.36(17) . . ?
C12 C11 C1 122.43(16) . . ?
C16 C11 C1 120.20(16) . . ?
O1 C12 C11 123.10(17) . . ?
O1 C12 C13 114.97(18) . . ?
C11 C12 C13 121.93(18) . . ?
C14 C13 C12 119.3(2) . . ?
C14 C13 H13 120.4 . . ?
C12 C13 H13 120.4 . . ?
C13 C14 C15 120.2(2) . . ?
C13 C14 H14 119.9 . . ?
C15 C14 H14 119.9 . . ?
C16 C15 C14 119.8(2) . . ?
C16 C15 H15 120.1 . . ?
C14 C15 H15 120.1 . . ?
C15 C16 C11 121.4(2) . . ?
C15 C16 H16 119.3 . . ?
C11 C16 H16 119.3 . . ?
C22 C21 C26 117.02(18) . . ?
C22 C21 C1 122.25(16) . . ?
C26 C21 C1 120.64(17) . . ?
O1 C22 C21 123.12(17) . . ?
O1 C22 C23 114.87(18) . . ?
C21 C22 C23 122.01(19) . . ?
C24 C23 C22 119.3(2) . . ?
C24 C23 H23 120.3 . . ?
C22 C23 H23 120.3 . . ?
C23 C24 C25 120.0(2) . . ?
C23 C24 H24 120.0 . . ?
C25 C24 H24 120.0 . . ?
C26 C25 C24 119.9(2) . . ?
C26 C25 H25 120.1 . . ?
C24 C25 H25 120.1 . . ?
C25 C26 C21 121.8(2) . . ?
C25 C26 H26 119.1 . . ?
C21 C26 H26 119.1 . . ?
C32 C31 C36 118.84(19) . . ?
C32 C31 C1 123.75(18) . . ?
C36 C31 C1 117.38(17) . . ?
C31 C32 C33 119.4(2) . . ?
C31 C32 H32 120.3 . . ?
C33 C32 H32 120.3 . . ?
C34 C33 C32 121.0(2) . . ?
C34 C33 H33 119.5 . . ?
C32 C33 H33 119.5 . . ?
C33 C34 C35 119.9(2) . . ?
C33 C34 H34 120.0 . . ?
C35 C34 H34 120.0 . . ?
C34 C35 C36 119.6(2) . . ?
C34 C35 H35 120.2 . . ?
C36 C35 H35 120.2 . . ?
C35 C36 C31 121.3(2) . . ?
C35 C36 H36 119.3 . . ?
C31 C36 H36 119.3 . . ?
C42 C41 C46 117.72(19) . . ?
C42 C41 C6 122.67(17) . . ?
C46 C41 C6 119.58(18) . . ?
O2 C42 C41 123.09(17) . . ?
O2 C42 C43 115.45(18) . . ?
C41 C42 C43 121.46(19) . . ?
C44 C43 C42 119.5(2) . . ?
C44 C43 H43 120.2 . . ?
C42 C43 H43 120.2 . . ?
C43 C44 C45 120.4(2) . . ?
C43 C44 H44 119.8 . . ?
C45 C44 H44 119.8 . . ?
C44 C45 C46 119.4(2) . . ?
C44 C45 H45 120.3 . . ?
C46 C45 H45 120.3 . . ?
C45 C46 C41 121.6(2) . . ?
C45 C46 H46 119.2 . . ?
C41 C46 H46 119.2 . . ?
C52 C51 C56 117.13(19) . . ?
C52 C51 C6 122.62(17) . . ?
C56 C51 C6 120.24(18) . . ?
O2 C52 C51 122.73(17) . . ?
O2 C52 C53 115.10(18) . . ?
C51 C52 C53 122.17(19) . . ?
C54 C53 C52 119.4(2) . . ?
C54 C53 H53 120.3 . . ?
C52 C53 H53 120.3 . . ?
C53 C54 C55 120.1(2) . . ?
C53 C54 H54 119.9 . . ?
C55 C54 H54 119.9 . . ?
C56 C55 C54 119.8(2) . . ?
C56 C55 H55 120.1 . . ?
C54 C55 H55 120.1 . . ?
C55 C56 C51 121.4(2) . . ?
C55 C56 H56 119.3 . . ?
C51 C56 H56 119.3 . . ?
C62 C61 C66 118.35(19) . . ?
C62 C61 C6 123.19(18) . . ?
C66 C61 C6 118.44(17) . . ?
C61 C62 C63 120.2(2) . . ?
C61 C62 H62 119.9 . . ?
C63 C62 H62 119.9 . . ?
C64 C63 C62 120.7(2) . . ?
C64 C63 H63 119.6 . . ?
C62 C63 H63 119.6 . . ?
C63 C64 C65 119.6(2) . . ?
C63 C64 H64 120.2 . . ?
C65 C64 H64 120.2 . . ?
C64 C65 C66 119.8(2) . . ?
C64 C65 H65 120.1 . . ?
C66 C65 H65 120.1 . . ?
C61 C66 C65 121.3(2) . . ?
C61 C66 H66 119.3 . . ?
C65 C66 H66 119.3 . . ?
C76 C71 C72 120.2(2) . . ?
C76 C71 Cl71 119.1(2) . . ?
C72 C71 Cl71 120.7(2) . . ?
C73 C72 C71 118.9(3) . . ?
C73 C72 Cl72 119.4(2) . . ?
C71 C72 Cl72 121.7(2) . . ?
C74 C73 C72 120.7(3) . . ?
C74 C73 H73 119.6 . . ?
C72 C73 H73 119.6 . . ?
C75 C74 C73 119.7(3) . . ?
C75 C74 H74 120.2 . . ?
C73 C74 H74 120.2 . . ?
C76 C75 C74 120.1(3) . . ?
C76 C75 H75 119.9 . . ?
C74 C75 H75 119.9 . . ?
C75 C76 C71 120.3(3) . . ?
C75 C76 H76 119.8 . . ?
C71 C76 H76 119.8 . . ?
C86 C81 C82 120.6(10) . . ?
C86 C81 Cl81 119.7(7) . . ?
C82 C81 Cl81 119.8(7) . . ?
C81 C82 C83 122.0(10) . . ?
C81 C82 Cl82 121.6(8) . . ?
C83 C82 Cl82 116.5(9) . . ?
C84 C83 C82 108.1(9) . . ?
C84 C83 H83 125.9 . . ?
C82 C83 H83 125.9 . . ?
C85 C84 C83 132.2(11) . . ?
C85 C84 H84 113.9 . . ?
C83 C84 H84 113.9 . . ?
C84 C85 C86 114.4(12) . . ?
C84 C85 H85 122.8 . . ?
C86 C85 H85 122.8 . . ?
C81 C86 C85 122.6(13) . . ?
C81 C86 H86 118.7 . . ?
C85 C86 H86 118.7 . . ?

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
C2 N1 C1 C11 -68.0(2) . . . . ?
C2 N1 C1 C21 52.9(2) . . . . ?
C2 N1 C1 C31 174.74(16) . . . . ?
C1 N1 C2 C3 167.21(18) . . . . ?
N1 C2 C3 C4 176.33(19) . . . . ?
C2 C3 C4 C5 -179.9(2) . . . . ?
C6 N2 C5 C4 -170.04(18) . . . . ?
C3 C4 C5 N2 -175.77(19) . . . . ?
C5 N2 C6 C41 -58.0(2) . . . . ?
C5 N2 C6 C51 63.3(2) . . . . ?
C5 N2 C6 C61 -177.42(17) . . . . ?
N1 C1 C11 C12 113.48(19) . . . . ?
C21 C1 C11 C12 -9.5(2) . . . . ?
C31 C1 C11 C12 -128.28(18) . . . . ?
N1 C1 C11 C16 -67.2(2) . . . . ?
C21 C1 C11 C16 169.76(16) . . . . ?
C31 C1 C11 C16 51.0(2) . . . . ?
C22 O1 C12 C11 9.8(3) . . . . ?
C22 O1 C12 C13 -170.00(18) . . . . ?
C16 C11 C12 O1 -179.97(18) . . . . ?
C1 C11 C12 O1 -0.6(3) . . . . ?
C16 C11 C12 C13 -0.1(3) . . . . ?
C1 C11 C12 C13 179.19(18) . . . . ?
O1 C12 C13 C14 179.87(19) . . . . ?
C11 C12 C13 C14 0.0(3) . . . . ?
C12 C13 C14 C15 -0.1(3) . . . . ?
C13 C14 C15 C16 0.3(4) . . . . ?
C14 C15 C16 C11 -0.4(3) . . . . ?
C12 C11 C16 C15 0.3(3) . . . . ?
C1 C11 C16 C15 -179.03(18) . . . . ?
N1 C1 C21 C22 -108.5(2) . . . . ?
C11 C1 C21 C22 11.8(2) . . . . ?
C31 C1 C21 C22 129.63(18) . . . . ?
N1 C1 C21 C26 68.1(2) . . . . ?
C11 C1 C21 C26 -171.66(17) . . . . ?
C31 C1 C21 C26 -53.8(2) . . . . ?
C12 O1 C22 C21 -7.5(3) . . . . ?
C12 O1 C22 C23 172.09(18) . . . . ?
C26 C21 C22 O1 179.25(19) . . . . ?
C1 C21 C22 O1 -4.1(3) . . . . ?
C26 C21 C22 C23 -0.3(3) . . . . ?
C1 C21 C22 C23 176.41(18) . . . . ?
O1 C22 C23 C24 -179.6(2) . . . . ?
C21 C22 C23 C24 0.0(3) . . . . ?
C22 C23 C24 C25 0.4(3) . . . . ?
C23 C24 C25 C26 -0.5(4) . . . . ?
C24 C25 C26 C21 0.2(4) . . . . ?
C22 C21 C26 C25 0.2(3) . . . . ?
C1 C21 C26 C25 -176.6(2) . . . . ?
N1 C1 C31 C32 0.1(2) . . . . ?
C11 C1 C31 C32 -117.27(19) . . . . ?
C21 C1 C31 C32 123.97(19) . . . . ?
N1 C1 C31 C36 178.29(16) . . . . ?
C11 C1 C31 C36 60.9(2) . . . . ?
C21 C1 C31 C36 -57.8(2) . . . . ?
C36 C31 C32 C33 -0.1(3) . . . . ?
C1 C31 C32 C33 178.05(18) . . . . ?
C31 C32 C33 C34 0.3(3) . . . . ?
C32 C33 C34 C35 -0.1(4) . . . . ?
C33 C34 C35 C36 -0.2(3) . . . . ?
C34 C35 C36 C31 0.4(3) . . . . ?
C32 C31 C36 C35 -0.3(3) . . . . ?
C1 C31 C36 C35 -178.54(18) . . . . ?
N2 C6 C41 C42 127.67(19) . . . . ?
C51 C6 C41 C42 6.6(2) . . . . ?
C61 C6 C41 C42 -112.7(2) . . . . ?
N2 C6 C41 C46 -54.2(2) . . . . ?
C51 C6 C41 C46 -175.31(17) . . . . ?
C61 C6 C41 C46 65.4(2) . . . . ?
C52 O2 C42 C41 -6.8(3) . . . . ?
C52 O2 C42 C43 172.84(18) . . . . ?
C46 C41 C42 O2 -179.52(19) . . . . ?
C6 C41 C42 O2 -1.4(3) . . . . ?
C46 C41 C42 C43 0.9(3) . . . . ?
C6 C41 C42 C43 178.99(19) . . . . ?
O2 C42 C43 C44 -179.9(2) . . . . ?
C41 C42 C43 C44 -0.2(3) . . . . ?
C42 C43 C44 C45 -0.4(4) . . . . ?
C43 C44 C45 C46 0.4(4) . . . . ?
C44 C45 C46 C41 0.3(4) . . . . ?
C42 C41 C46 C45 -0.9(3) . . . . ?
C6 C41 C46 C45 -179.1(2) . . . . ?
N2 C6 C51 C52 -126.89(18) . . . . ?
C41 C6 C51 C52 -4.4(2) . . . . ?
C61 C6 C51 C52 114.28(19) . . . . ?
N2 C6 C51 C56 51.7(2) . . . . ?
C41 C6 C51 C56 174.23(18) . . . . ?
C61 C6 C51 C56 -67.1(2) . . . . ?
C42 O2 C52 C51 9.1(3) . . . . ?
C42 O2 C52 C53 -171.10(17) . . . . ?
C56 C51 C52 O2 178.16(18) . . . . ?
C6 C51 C52 O2 -3.2(3) . . . . ?
C56 C51 C52 C53 -1.7(3) . . . . ?
C6 C51 C52 C53 177.02(18) . . . . ?
O2 C52 C53 C54 -178.39(19) . . . . ?
C51 C52 C53 C54 1.4(3) . . . . ?
C52 C53 C54 C55 -0.3(3) . . . . ?
C53 C54 C55 C56 -0.5(4) . . . . ?
C54 C55 C56 C51 0.2(4) . . . . ?
C52 C51 C56 C55 0.8(3) . . . . ?
C6 C51 C56 C55 -177.9(2) . . . . ?
N2 C6 C61 C62 -1.9(3) . . . . ?
C41 C6 C61 C62 -123.3(2) . . . . ?
C51 C6 C61 C62 117.2(2) . . . . ?
N2 C6 C61 C66 176.64(19) . . . . ?
C41 C6 C61 C66 55.3(2) . . . . ?
C51 C6 C61 C66 -64.2(2) . . . . ?
C66 C61 C62 C63 0.4(3) . . . . ?
C6 C61 C62 C63 179.0(2) . . . . ?
C61 C62 C63 C64 -0.1(4) . . . . ?
C62 C63 C64 C65 -0.5(4) . . . . ?
C63 C64 C65 C66 0.8(4) . . . . ?
C62 C61 C66 C65 -0.1(3) . . . . ?
C6 C61 C66 C65 -178.7(2) . . . . ?
C64 C65 C66 C61 -0.5(4) . . . . ?
C76 C71 C72 C73 0.4(4) . . . . ?
Cl71 C71 C72 C73 -179.1(2) . . . . ?
C76 C71 C72 Cl72 -178.8(2) . . . . ?
Cl71 C71 C72 Cl72 1.6(3) . . . . ?
C71 C72 C73 C74 -0.3(4) . . . . ?
Cl72 C72 C73 C74 178.9(2) . . . . ?
C72 C73 C74 C75 -0.3(5) . . . . ?
C73 C74 C75 C76 0.8(5) . . . . ?
C74 C75 C76 C71 -0.7(5) . . . . ?
C72 C71 C76 C75 0.1(4) . . . . ?
Cl71 C71 C76 C75 179.6(2) . . . . ?
C86 C81 C82 C83 2(6) . . . . ?
Cl81 C81 C82 C83 -178(2) . . . . ?
C86 C81 C82 Cl82 -178.6(6) . . . . ?
Cl81 C81 C82 Cl82 1(4) . . . . ?
C81 C82 C83 C84 -3(4) . . . . ?
Cl82 C82 C83 C84 177.1(18) . . . . ?
C82 C83 C84 C85 3(2) . . . . ?
C83 C84 C85 C86 0(3) . . . . ?
C82 C81 C86 C85 1(6) . . . . ?
Cl81 C81 C86 C85 -179(2) . . . . ?
C84 C85 C86 C81 -2(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
_geom_hbond_publ_flag
C32 H32 N1 0.95 2.46 2.808(3) 102 . yes
C34 H34 O2 0.95 2.46 3.389(3) 167 2_666 yes
C62 H62 N2 0.95 2.42 2.779(3) 102 . yes

_refine_diff_density_max         0.780
_refine_diff_density_min         -0.643
_refine_diff_density_rms         0.068

