# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2022

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

data_1BdotCDCl3
_database_code_depnum_ccdc_archive 'CCDC 2092859'
loop_
_audit_author_name
_audit_author_address
'Mark Elsegood'
;Loughborough University
United Kingdom
;
_audit_update_record             
;
2021-06-28 deposited with the CCDC.	2022-03-24 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         'C44 H28 N4 O2, C D Cl3'
_chemical_formula_sum            'C45 H28 Cl3 D N4 O2'
_chemical_formula_weight         765.08

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0037 0.0018 '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 0.0071 0.0036 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0121 0.0066 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1567 0.1694 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
D D 0.0000 0.0000 '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                   10.6041(7)
_cell_length_b                   11.1981(7)
_cell_length_c                   15.4055(10)
_cell_angle_alpha                78.882(3)
_cell_angle_beta                 82.039(3)
_cell_angle_gamma                80.742(3)
_cell_volume                     1760.7(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9939
_cell_measurement_theta_min      2.57
_cell_measurement_theta_max      31.36

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.443
_exptl_crystal_F_000             788
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.070
_exptl_absorpt_coefficient_mu    0.325
_shelx_estimated_absorpt_T_min   0.962
_shelx_estimated_absorpt_T_max   0.978
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.962
_exptl_absorpt_correction_T_max  0.978
_exptl_absorpt_process_details   'TWINABS v2012/1, Sheldrick, G.M., (2012)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.7288
_diffrn_radiation_type           synchrotron
_diffrn_source                   'Advanced Light Source station 12.2.1'
_diffrn_measurement_device_type  'Bruker D8 with PHOTON 100 detector'
_diffrn_radiation_monochromator  'silicon 111'
_diffrn_measurement_method       'ω/θ shutterless scans'
_diffrn_detector_area_resol_mean 10.42
_diffrn_reflns_number            10733
_diffrn_reflns_av_unetI/netI     0.0299
_diffrn_reflns_av_R_equivalents  0.0455
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.164
_diffrn_reflns_theta_max         31.433
_diffrn_reflns_theta_full        25.930
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             10733
_reflns_number_gt                9162
_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 APEX 2'
_computing_cell_refinement       'Bruker SAINT v8.38a'
_computing_data_reduction        'Bruker SAINT v8.38a'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0666P)²+0.5619P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         10733
_refine_ls_number_parameters     487
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0497
_refine_ls_R_factor_gt           0.0432
_refine_ls_wR_factor_ref         0.1254
_refine_ls_wR_factor_gt          0.1214
_refine_ls_goodness_of_fit_ref   1.107
_refine_ls_restrained_S_all      1.107
_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
N1 N 0.16797(10) 0.60537(9) 0.07158(8) 0.0197(2) Uani 1 1 d . . . . .
C1 C 0.25481(11) 0.66668(10) 0.00761(8) 0.0176(2) Uani 1 1 d . . . . .
C2 C 0.36195(11) 0.60600(11) -0.03691(9) 0.0203(2) Uani 1 1 d . . . . .
H2 H 0.377279 0.518752 -0.025614 0.024 Uiso 1 1 calc R U . . .
C3 C 0.44727(12) 0.67145(12) -0.09795(9) 0.0220(2) Uani 1 1 d . . . . .
H3 H 0.519792 0.628472 -0.127769 0.026 Uiso 1 1 calc R U . . .
C4 C 0.42661(12) 0.79889(12) -0.11523(9) 0.0231(2) Uani 1 1 d . . . . .
H4 H 0.483910 0.843418 -0.157359 0.028 Uiso 1 1 calc R U . . .
C5 C 0.32119(12) 0.86070(11) -0.07023(9) 0.0214(2) Uani 1 1 d . . . . .
H5 H 0.307048 0.947976 -0.080865 0.026 Uiso 1 1 calc R U . . .
C6 C 0.23678(11) 0.79557(11) -0.01000(9) 0.0186(2) Uani 1 1 d . . . . .
O1 O 0.13738(9) 0.86441(8) 0.03479(7) 0.02287(19) Uani 1 1 d . . . . .
C7 C 0.04276(11) 0.80246(11) 0.08657(8) 0.0182(2) Uani 1 1 d . . . . .
C8 C -0.06539(12) 0.87409(11) 0.11905(9) 0.0217(2) Uani 1 1 d . . . . .
H8 H -0.071994 0.961128 0.105071 0.026 Uiso 1 1 calc R U . . .
C9 C -0.16467(13) 0.81886(13) 0.17224(9) 0.0253(3) Uani 1 1 d . . . . .
H9 H -0.238948 0.867754 0.195060 0.030 Uiso 1 1 calc R U . . .
C10 C -0.15399(12) 0.69170(13) 0.19156(9) 0.0244(3) Uani 1 1 d . . . . .
H10 H -0.221785 0.653319 0.227242 0.029 Uiso 1 1 calc R U . . .
C11 C -0.04452(12) 0.61992(11) 0.15900(8) 0.0200(2) Uani 1 1 d . . . . .
H11 H -0.038366 0.532910 0.172918 0.024 Uiso 1 1 calc R U . . .
C12 C 0.05607(11) 0.67388(11) 0.10631(8) 0.0174(2) Uani 1 1 d . . . . .
C13 C 0.18491(11) 0.47412(10) 0.09285(8) 0.0179(2) Uani 1 1 d . . . . .
C14 C 0.17985(12) 0.40522(11) 0.02762(9) 0.0192(2) Uani 1 1 d . . . . .
H14 H 0.163170 0.445403 -0.030660 0.023 Uiso 1 1 calc R U . . .
C15 C 0.19920(12) 0.27737(11) 0.04769(8) 0.0192(2) Uani 1 1 d . . . . .
H15 H 0.199529 0.230503 0.002385 0.023 Uiso 1 1 calc R U . . .
C16 C 0.21805(11) 0.21813(10) 0.13388(8) 0.0169(2) Uani 1 1 d . . . . .
C17 C 0.21958(11) 0.28768(10) 0.19978(8) 0.0182(2) Uani 1 1 d . . . . .
H17 H 0.230245 0.247802 0.259107 0.022 Uiso 1 1 calc R U . . .
C18 C 0.20546(12) 0.41559(11) 0.17858(9) 0.0193(2) Uani 1 1 d . . . . .
H18 H 0.209936 0.462640 0.222930 0.023 Uiso 1 1 calc R U . . .
C19 C 0.23996(11) 0.08119(10) 0.15534(8) 0.0162(2) Uani 1 1 d . . . . .
N2 N 0.34403(9) 0.02678(9) 0.11399(7) 0.01774(19) Uani 1 1 d . . . . .
C20 C 0.37255(11) -0.09775(10) 0.13772(8) 0.0166(2) Uani 1 1 d . . . . .
C21 C 0.48530(11) -0.15948(11) 0.09683(9) 0.0198(2) Uani 1 1 d . . . . .
H21 H 0.539631 -0.115002 0.052249 0.024 Uiso 1 1 calc R U . . .
C22 C 0.51573(12) -0.28406(11) 0.12197(9) 0.0210(2) Uani 1 1 d . . . . .
H22 H 0.591813 -0.325584 0.094848 0.025 Uiso 1 1 calc R U . . .
C23 C 0.43526(12) -0.35124(11) 0.18769(9) 0.0211(2) Uani 1 1 d . . . . .
H23 H 0.457940 -0.437436 0.204443 0.025 Uiso 1 1 calc R U . . .
C24 C 0.32465(12) -0.29345(11) 0.22765(8) 0.0197(2) Uani 1 1 d . . . . .
H24 H 0.270585 -0.339586 0.271310 0.024 Uiso 1 1 calc R U . . .
C25 C 0.29150(11) -0.16511(10) 0.20361(8) 0.0166(2) Uani 1 1 d . . . . .
N3 N 0.18082(9) -0.10798(9) 0.24308(7) 0.01682(19) Uani 1 1 d . . . . .
C26 C 0.15455(10) 0.01259(10) 0.21932(8) 0.0157(2) Uani 1 1 d . . . . .
C27 C 0.02979(11) 0.07037(10) 0.25937(8) 0.0167(2) Uani 1 1 d . . . . .
C28 C -0.01180(11) 0.03079(11) 0.34883(9) 0.0200(2) Uani 1 1 d . . . . .
H28 H 0.044329 -0.025346 0.385383 0.024 Uiso 1 1 calc R U . . .
C29 C -0.13507(12) 0.07305(12) 0.38489(9) 0.0224(2) Uani 1 1 d . . . . .
H29 H -0.162159 0.047168 0.446117 0.027 Uiso 1 1 calc R U . . .
C30 C -0.21807(11) 0.15296(11) 0.33119(9) 0.0218(2) Uani 1 1 d . . . . .
N4 N -0.34962(10) 0.18279(10) 0.36556(9) 0.0256(2) Uani 1 1 d . . . . .
C31 C -0.17638(11) 0.19699(11) 0.24279(9) 0.0213(2) Uani 1 1 d . . . . .
H31 H -0.232200 0.254526 0.206849 0.026 Uiso 1 1 calc R U . . .
C32 C -0.05267(11) 0.15634(11) 0.20739(9) 0.0194(2) Uani 1 1 d . . . . .
H32 H -0.023777 0.187217 0.147303 0.023 Uiso 1 1 calc R U . . .
C33 C -0.40106(12) 0.30399(11) 0.37312(9) 0.0209(2) Uani 1 1 d . . . . .
C34 C -0.32533(12) 0.39699(12) 0.36547(9) 0.0224(2) Uani 1 1 d . . . . .
H34 H -0.234829 0.379662 0.351874 0.027 Uiso 1 1 calc R U . . .
C35 C -0.38048(13) 0.51514(12) 0.37748(9) 0.0238(2) Uani 1 1 d . . . . .
H35 H -0.327302 0.577312 0.372541 0.029 Uiso 1 1 calc R U . . .
C36 C -0.51239(13) 0.54250(12) 0.39658(9) 0.0253(3) Uani 1 1 d . . . . .
H36 H -0.549816 0.623136 0.404632 0.030 Uiso 1 1 calc R U . . .
C37 C -0.58958(12) 0.45085(12) 0.40386(9) 0.0239(2) Uani 1 1 d . . . . .
H37 H -0.680191 0.469050 0.416281 0.029 Uiso 1 1 calc R U . . .
C38 C -0.53467(12) 0.33365(12) 0.39308(9) 0.0223(2) Uani 1 1 d . . . . .
O2 O -0.61748(9) 0.24656(9) 0.40517(8) 0.0321(2) Uani 1 1 d . . . . .
C39 C -0.56633(12) 0.13024(12) 0.39036(9) 0.0221(2) Uani 1 1 d . . . . .
C40 C -0.65274(12) 0.04806(13) 0.39658(9) 0.0250(3) Uani 1 1 d . . . . .
H40 H -0.741982 0.073074 0.410701 0.030 Uiso 1 1 calc R U . . .
C41 C -0.60908(14) -0.07175(14) 0.38214(10) 0.0288(3) Uani 1 1 d . . . . .
H41 H -0.667909 -0.129135 0.387658 0.035 Uiso 1 1 calc R U . . .
C42 C -0.47904(14) -0.10589(14) 0.35968(11) 0.0308(3) Uani 1 1 d . . . . .
H42 H -0.448685 -0.186742 0.348652 0.037 Uiso 1 1 calc R U . . .
C43 C -0.39223(13) -0.02235(13) 0.35312(10) 0.0271(3) Uani 1 1 d . . . . .
H43 H -0.303300 -0.046899 0.337411 0.032 Uiso 1 1 calc R U . . .
C44 C -0.43425(12) 0.09648(12) 0.36930(9) 0.0218(2) Uani 1 1 d . . . . .
C45 C 0.01181(12) -0.30682(12) 0.39654(9) 0.0236(2) Uani 1 1 d . . . . .
H45 D 0.025539 -0.250433 0.338292 0.028 Uiso 1 1 calc R U . . .
Cl1 Cl 0.12720(3) -0.29299(3) 0.46504(2) 0.03090(9) Uani 1 1 d . . . . .
Cl2 Cl 0.03135(3) -0.45941(3) 0.37716(2) 0.02801(8) Uani 1 1 d . . . . .
Cl3 Cl -0.14461(3) -0.26645(3) 0.44670(3) 0.03272(9) Uani 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
N1 C12 1.4044(15) . ?
N1 C1 1.4077(15) . ?
N1 C13 1.4302(14) . ?
C1 C2 1.3923(16) . ?
C1 C6 1.4028(16) . ?
C2 C3 1.3970(17) . ?
C2 H2 0.9500 . ?
C3 C4 1.3873(18) . ?
C3 H3 0.9500 . ?
C4 C5 1.3894(18) . ?
C4 H4 0.9500 . ?
C5 C6 1.3831(16) . ?
C5 H5 0.9500 . ?
C6 O1 1.3870(15) . ?
O1 C7 1.3832(14) . ?
C7 C8 1.3815(16) . ?
C7 C12 1.4012(16) . ?
C8 C9 1.3919(19) . ?
C8 H8 0.9500 . ?
C9 C10 1.3867(19) . ?
C9 H9 0.9500 . ?
C10 C11 1.3926(17) . ?
C10 H10 0.9500 . ?
C11 C12 1.3929(16) . ?
C11 H11 0.9500 . ?
C13 C18 1.3862(18) . ?
C13 C14 1.3911(17) . ?
C14 C15 1.3927(16) . ?
C14 H14 0.9500 . ?
C15 C16 1.3908(18) . ?
C15 H15 0.9500 . ?
C16 C17 1.3967(16) . ?
C16 C19 1.4920(15) . ?
C17 C18 1.3946(15) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C19 N2 1.3166(14) . ?
C19 C26 1.4376(15) . ?
N2 C20 1.3668(14) . ?
C20 C21 1.4133(16) . ?
C20 C25 1.4176(15) . ?
C21 C22 1.3718(17) . ?
C21 H21 0.9500 . ?
C22 C23 1.4116(17) . ?
C22 H22 0.9500 . ?
C23 C24 1.3722(17) . ?
C23 H23 0.9500 . ?
C24 C25 1.4122(16) . ?
C24 H24 0.9500 . ?
C25 N3 1.3665(14) . ?
N3 C26 1.3233(14) . ?
C26 C27 1.4839(15) . ?
C27 C28 1.3962(17) . ?
C27 C32 1.3993(17) . ?
C28 C29 1.3937(16) . ?
C28 H28 0.9500 . ?
C29 C30 1.3866(19) . ?
C29 H29 0.9500 . ?
C30 C31 1.3919(19) . ?
C30 N4 1.4323(15) . ?
N4 C33 1.3994(16) . ?
N4 C44 1.4093(15) . ?
C31 C32 1.3896(16) . ?
C31 H31 0.9500 . ?
C32 H32 0.9500 . ?
C33 C34 1.3925(17) . ?
C33 C38 1.4069(17) . ?
C34 C35 1.3936(18) . ?
C34 H34 0.9500 . ?
C35 C36 1.3856(19) . ?
C35 H35 0.9500 . ?
C36 C37 1.3915(19) . ?
C36 H36 0.9500 . ?
C37 C38 1.3785(18) . ?
C37 H37 0.9500 . ?
C38 O2 1.3847(15) . ?
O2 C39 1.3769(16) . ?
C39 C40 1.3816(17) . ?
C39 C44 1.4004(17) . ?
C40 C41 1.397(2) . ?
C40 H40 0.9500 . ?
C41 C42 1.384(2) . ?
C41 H41 0.9500 . ?
C42 C43 1.3956(18) . ?
C42 H42 0.9500 . ?
C43 C44 1.3920(18) . ?
C43 H43 0.9500 . ?
C45 Cl3 1.7582(13) . ?
C45 Cl1 1.7653(14) . ?
C45 Cl2 1.7656(14) . ?
C45 H45 1.0000 . ?

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 N1 C1 118.90(10) . . ?
C12 N1 C13 120.07(10) . . ?
C1 N1 C13 120.59(10) . . ?
C2 C1 C6 117.67(11) . . ?
C2 C1 N1 123.31(10) . . ?
C6 C1 N1 118.96(10) . . ?
C1 C2 C3 121.02(11) . . ?
C1 C2 H2 119.5 . . ?
C3 C2 H2 119.5 . . ?
C4 C3 C2 120.33(12) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C3 C4 C5 119.27(11) . . ?
C3 C4 H4 120.4 . . ?
C5 C4 H4 120.4 . . ?
C6 C5 C4 120.22(11) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
C5 C6 O1 116.44(10) . . ?
C5 C6 C1 121.48(11) . . ?
O1 C6 C1 122.02(10) . . ?
C7 O1 C6 117.32(9) . . ?
C8 C7 O1 116.48(10) . . ?
C8 C7 C12 121.49(11) . . ?
O1 C7 C12 122.02(10) . . ?
C7 C8 C9 120.07(12) . . ?
C7 C8 H8 120.0 . . ?
C9 C8 H8 120.0 . . ?
C10 C9 C8 119.29(12) . . ?
C10 C9 H9 120.4 . . ?
C8 C9 H9 120.4 . . ?
C9 C10 C11 120.42(12) . . ?
C9 C10 H10 119.8 . . ?
C11 C10 H10 119.8 . . ?
C10 C11 C12 120.95(11) . . ?
C10 C11 H11 119.5 . . ?
C12 C11 H11 119.5 . . ?
C11 C12 C7 117.78(11) . . ?
C11 C12 N1 123.01(10) . . ?
C7 C12 N1 119.21(10) . . ?
C18 C13 C14 120.00(11) . . ?
C18 C13 N1 120.02(11) . . ?
C14 C13 N1 119.98(11) . . ?
C13 C14 C15 120.06(12) . . ?
C13 C14 H14 120.0 . . ?
C15 C14 H14 120.0 . . ?
C16 C15 C14 120.17(11) . . ?
C16 C15 H15 119.9 . . ?
C14 C15 H15 119.9 . . ?
C15 C16 C17 119.57(10) . . ?
C15 C16 C19 120.25(11) . . ?
C17 C16 C19 120.16(11) . . ?
C18 C17 C16 120.07(11) . . ?
C18 C17 H17 120.0 . . ?
C16 C17 H17 120.0 . . ?
C13 C18 C17 120.05(11) . . ?
C13 C18 H18 120.0 . . ?
C17 C18 H18 120.0 . . ?
N2 C19 C26 121.81(10) . . ?
N2 C19 C16 116.12(10) . . ?
C26 C19 C16 122.05(10) . . ?
C19 N2 C20 117.50(10) . . ?
N2 C20 C21 119.40(10) . . ?
N2 C20 C25 120.80(10) . . ?
C21 C20 C25 119.80(10) . . ?
C22 C21 C20 119.54(11) . . ?
C22 C21 H21 120.2 . . ?
C20 C21 H21 120.2 . . ?
C21 C22 C23 120.73(11) . . ?
C21 C22 H22 119.6 . . ?
C23 C22 H22 119.6 . . ?
C24 C23 C22 120.74(11) . . ?
C24 C23 H23 119.6 . . ?
C22 C23 H23 119.6 . . ?
C23 C24 C25 119.74(11) . . ?
C23 C24 H24 120.1 . . ?
C25 C24 H24 120.1 . . ?
N3 C25 C24 119.58(10) . . ?
N3 C25 C20 120.96(10) . . ?
C24 C25 C20 119.44(10) . . ?
C26 N3 C25 117.46(10) . . ?
N3 C26 C19 121.34(10) . . ?
N3 C26 C27 115.92(10) . . ?
C19 C26 C27 122.69(10) . . ?
C28 C27 C32 118.90(11) . . ?
C28 C27 C26 119.63(11) . . ?
C32 C27 C26 121.23(11) . . ?
C29 C28 C27 120.48(12) . . ?
C29 C28 H28 119.8 . . ?
C27 C28 H28 119.8 . . ?
C30 C29 C28 119.84(12) . . ?
C30 C29 H29 120.1 . . ?
C28 C29 H29 120.1 . . ?
C29 C30 C31 120.32(11) . . ?
C29 C30 N4 119.36(12) . . ?
C31 C30 N4 120.17(12) . . ?
C33 N4 C44 118.86(10) . . ?
C33 N4 C30 120.78(10) . . ?
C44 N4 C30 118.28(10) . . ?
C32 C31 C30 119.64(12) . . ?
C32 C31 H31 120.2 . . ?
C30 C31 H31 120.2 . . ?
C31 C32 C27 120.67(12) . . ?
C31 C32 H32 119.7 . . ?
C27 C32 H32 119.7 . . ?
C34 C33 N4 122.95(11) . . ?
C34 C33 C38 117.72(11) . . ?
N4 C33 C38 119.28(11) . . ?
C33 C34 C35 120.90(12) . . ?
C33 C34 H34 119.6 . . ?
C35 C34 H34 119.6 . . ?
C36 C35 C34 120.42(12) . . ?
C36 C35 H35 119.8 . . ?
C34 C35 H35 119.8 . . ?
C35 C36 C37 119.43(12) . . ?
C35 C36 H36 120.3 . . ?
C37 C36 H36 120.3 . . ?
C38 C37 C36 120.05(12) . . ?
C38 C37 H37 120.0 . . ?
C36 C37 H37 120.0 . . ?
C37 C38 O2 116.48(11) . . ?
C37 C38 C33 121.48(12) . . ?
O2 C38 C33 122.02(11) . . ?
C39 O2 C38 117.77(10) . . ?
O2 C39 C40 116.34(11) . . ?
O2 C39 C44 122.26(11) . . ?
C40 C39 C44 121.40(12) . . ?
C39 C40 C41 120.09(12) . . ?
C39 C40 H40 120.0 . . ?
C41 C40 H40 120.0 . . ?
C42 C41 C40 119.21(12) . . ?
C42 C41 H41 120.4 . . ?
C40 C41 H41 120.4 . . ?
C41 C42 C43 120.45(13) . . ?
C41 C42 H42 119.8 . . ?
C43 C42 H42 119.8 . . ?
C44 C43 C42 120.87(12) . . ?
C44 C43 H43 119.6 . . ?
C42 C43 H43 119.6 . . ?
C43 C44 C39 117.96(11) . . ?
C43 C44 N4 122.74(11) . . ?
C39 C44 N4 119.30(11) . . ?
Cl3 C45 Cl1 110.62(8) . . ?
Cl3 C45 Cl2 110.08(7) . . ?
Cl1 C45 Cl2 109.38(7) . . ?
Cl3 C45 H45 108.9 . . ?
Cl1 C45 H45 108.9 . . ?
Cl2 C45 H45 108.9 . . ?

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
C12 N1 C1 C2 -173.78(11) . . . . ?
C13 N1 C1 C2 -1.43(19) . . . . ?
C12 N1 C1 C6 9.11(17) . . . . ?
C13 N1 C1 C6 -178.54(11) . . . . ?
C6 C1 C2 C3 -0.94(19) . . . . ?
N1 C1 C2 C3 -178.09(12) . . . . ?
C1 C2 C3 C4 0.1(2) . . . . ?
C2 C3 C4 C5 0.9(2) . . . . ?
C3 C4 C5 C6 -1.1(2) . . . . ?
C4 C5 C6 O1 177.28(11) . . . . ?
C4 C5 C6 C1 0.20(19) . . . . ?
C2 C1 C6 C5 0.80(19) . . . . ?
N1 C1 C6 C5 178.07(12) . . . . ?
C2 C1 C6 O1 -176.12(11) . . . . ?
N1 C1 C6 O1 1.15(18) . . . . ?
C5 C6 O1 C7 171.90(11) . . . . ?
C1 C6 O1 C7 -11.03(17) . . . . ?
C6 O1 C7 C8 -169.95(11) . . . . ?
C6 O1 C7 C12 10.91(17) . . . . ?
O1 C7 C8 C9 -179.54(12) . . . . ?
C12 C7 C8 C9 -0.40(19) . . . . ?
C7 C8 C9 C10 -0.4(2) . . . . ?
C8 C9 C10 C11 0.7(2) . . . . ?
C9 C10 C11 C12 -0.2(2) . . . . ?
C10 C11 C12 C7 -0.61(19) . . . . ?
C10 C11 C12 N1 -179.65(12) . . . . ?
C8 C7 C12 C11 0.92(18) . . . . ?
O1 C7 C12 C11 -179.99(11) . . . . ?
C8 C7 C12 N1 180.00(12) . . . . ?
O1 C7 C12 N1 -0.91(18) . . . . ?
C1 N1 C12 C11 169.78(12) . . . . ?
C13 N1 C12 C11 -2.61(18) . . . . ?
C1 N1 C12 C7 -9.25(17) . . . . ?
C13 N1 C12 C7 178.36(11) . . . . ?
C12 N1 C13 C18 -69.45(15) . . . . ?
C1 N1 C13 C18 118.28(13) . . . . ?
C12 N1 C13 C14 110.09(13) . . . . ?
C1 N1 C13 C14 -62.17(16) . . . . ?
C18 C13 C14 C15 -1.91(18) . . . . ?
N1 C13 C14 C15 178.55(11) . . . . ?
C13 C14 C15 C16 2.82(18) . . . . ?
C14 C15 C16 C17 -1.07(17) . . . . ?
C14 C15 C16 C19 -179.46(10) . . . . ?
C15 C16 C17 C18 -1.58(17) . . . . ?
C19 C16 C17 C18 176.81(10) . . . . ?
C14 C13 C18 C17 -0.75(17) . . . . ?
N1 C13 C18 C17 178.80(10) . . . . ?
C16 C17 C18 C13 2.50(17) . . . . ?
C15 C16 C19 N2 62.59(15) . . . . ?
C17 C16 C19 N2 -115.79(13) . . . . ?
C15 C16 C19 C26 -119.14(13) . . . . ?
C17 C16 C19 C26 62.48(16) . . . . ?
C26 C19 N2 C20 -3.65(17) . . . . ?
C16 C19 N2 C20 174.62(10) . . . . ?
C19 N2 C20 C21 -178.23(11) . . . . ?
C19 N2 C20 C25 0.84(17) . . . . ?
N2 C20 C21 C22 178.51(12) . . . . ?
C25 C20 C21 C22 -0.57(18) . . . . ?
C20 C21 C22 C23 0.4(2) . . . . ?
C21 C22 C23 C24 0.2(2) . . . . ?
C22 C23 C24 C25 -0.7(2) . . . . ?
C23 C24 C25 N3 179.54(12) . . . . ?
C23 C24 C25 C20 0.61(18) . . . . ?
N2 C20 C25 N3 2.05(18) . . . . ?
C21 C20 C25 N3 -178.88(11) . . . . ?
N2 C20 C25 C24 -179.03(11) . . . . ?
C21 C20 C25 C24 0.04(18) . . . . ?
C24 C25 N3 C26 179.13(11) . . . . ?
C20 C25 N3 C26 -1.95(17) . . . . ?
C25 N3 C26 C19 -0.83(17) . . . . ?
C25 N3 C26 C27 176.37(10) . . . . ?
N2 C19 C26 N3 3.83(18) . . . . ?
C16 C19 C26 N3 -174.34(11) . . . . ?
N2 C19 C26 C27 -173.18(11) . . . . ?
C16 C19 C26 C27 8.66(18) . . . . ?
N3 C26 C27 C28 40.65(15) . . . . ?
C19 C26 C27 C28 -142.19(12) . . . . ?
N3 C26 C27 C32 -133.62(12) . . . . ?
C19 C26 C27 C32 43.54(16) . . . . ?
C32 C27 C28 C29 2.20(17) . . . . ?
C26 C27 C28 C29 -172.21(11) . . . . ?
C27 C28 C29 C30 1.36(18) . . . . ?
C28 C29 C30 C31 -3.87(19) . . . . ?
C28 C29 C30 N4 171.64(11) . . . . ?
C29 C30 N4 C33 118.47(14) . . . . ?
C31 C30 N4 C33 -66.01(18) . . . . ?
C29 C30 N4 C44 -78.11(17) . . . . ?
C31 C30 N4 C44 97.41(15) . . . . ?
C29 C30 C31 C32 2.77(18) . . . . ?
N4 C30 C31 C32 -172.71(11) . . . . ?
C30 C31 C32 C27 0.86(18) . . . . ?
C28 C27 C32 C31 -3.31(17) . . . . ?
C26 C27 C32 C31 171.00(11) . . . . ?
C44 N4 C33 C34 -176.48(13) . . . . ?
C30 N4 C33 C34 -13.2(2) . . . . ?
C44 N4 C33 C38 6.3(2) . . . . ?
C30 N4 C33 C38 169.64(13) . . . . ?
N4 C33 C34 C35 -177.07(13) . . . . ?
C38 C33 C34 C35 0.2(2) . . . . ?
C33 C34 C35 C36 -0.6(2) . . . . ?
C34 C35 C36 C37 0.1(2) . . . . ?
C35 C36 C37 C38 0.7(2) . . . . ?
C36 C37 C38 O2 177.29(13) . . . . ?
C36 C37 C38 C33 -1.1(2) . . . . ?
C34 C33 C38 C37 0.7(2) . . . . ?
N4 C33 C38 C37 178.02(13) . . . . ?
C34 C33 C38 O2 -177.65(13) . . . . ?
N4 C33 C38 O2 -0.3(2) . . . . ?
C37 C38 O2 C39 176.74(13) . . . . ?
C33 C38 O2 C39 -4.9(2) . . . . ?
C38 O2 C39 C40 -175.39(13) . . . . ?
C38 O2 C39 C44 4.0(2) . . . . ?
O2 C39 C40 C41 179.71(13) . . . . ?
C44 C39 C40 C41 0.3(2) . . . . ?
C39 C40 C41 C42 -1.4(2) . . . . ?
C40 C41 C42 C43 1.2(2) . . . . ?
C41 C42 C43 C44 0.3(2) . . . . ?
C42 C43 C44 C39 -1.4(2) . . . . ?
C42 C43 C44 N4 178.41(15) . . . . ?
O2 C39 C44 C43 -178.27(13) . . . . ?
C40 C39 C44 C43 1.1(2) . . . . ?
O2 C39 C44 N4 1.9(2) . . . . ?
C40 C39 C44 N4 -178.68(13) . . . . ?
C33 N4 C44 C43 173.09(14) . . . . ?
C30 N4 C44 C43 9.3(2) . . . . ?
C33 N4 C44 C39 -7.1(2) . . . . ?
C30 N4 C44 C39 -170.86(13) . . . . ?

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
C45 H45 N3 1.00 2.58 3.4408(16) 143.5 . yes

_refine_diff_density_max         0.637
_refine_diff_density_min         -0.616
_refine_diff_density_rms         0.062


#===END
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: deuterochlorform/methanol'
####################################################################### 
# 
# 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_2dot7CHCl3
_database_code_depnum_ccdc_archive 'CCDC 2092860'
loop_
_audit_author_name
_audit_author_address
'Mark Elsegood'
;Loughborough University
United Kingdom
;
_audit_update_record             
;
2021-06-28 deposited with the CCDC.	2022-03-24 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         'C134 H80 N12 O6, 7(C H Cl3)'
_chemical_formula_sum            'C141 H87 Cl21 N12 O6'
_chemical_formula_weight         2789.67

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           43
_space_group_name_H-M_alt        'F d d 2'
_space_group_name_Hall           'F 2 -2d'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'x+1/4, -y+1/4, z+1/4'
'-x+1/4, y+1/4, z+1/4'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'x+1/4, -y+3/4, z+3/4'
'-x+1/4, y+3/4, z+3/4'
'x+1/2, y, z+1/2'
'-x+1/2, -y, z+1/2'
'x+3/4, -y+1/4, z+3/4'
'-x+3/4, y+1/4, z+3/4'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z'
'x+3/4, -y+3/4, z+1/4'
'-x+3/4, y+3/4, z+1/4'

_cell_length_a                   55.721(3)
_cell_length_b                   20.5478(10)
_cell_length_c                   22.9320(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     26256(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    180(2)
_cell_measurement_reflns_used    9487
_cell_measurement_theta_min      2.99
_cell_measurement_theta_max      68.17

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.411
_exptl_crystal_F_000             11376
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    4.500
_shelx_estimated_absorpt_T_min   0.498
_shelx_estimated_absorpt_T_max   0.614
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.579
_exptl_absorpt_correction_T_max  0.753
_exptl_absorpt_process_details   'SADABS (Bruker, 2014)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      180(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Incoatec I\mS Cu microsource'
_diffrn_measurement_device_type  'Bruker D8-QUEST PHOTON-III CMOS'
_diffrn_measurement_method       'ω and φ-scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            142603
_diffrn_reflns_av_unetI/netI     0.0265
_diffrn_reflns_av_R_equivalents  0.0713
_diffrn_reflns_limit_h_min       -67
_diffrn_reflns_limit_h_max       67
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         3.172
_diffrn_reflns_theta_max         68.406
_diffrn_reflns_theta_full        67.679
_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 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             12043
_reflns_number_gt                11300
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.946
_reflns_Friedel_fraction_max     0.996
_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       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_reduction        'SAINT (Bruker, 2016)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008) & SHELXTL'
_computing_publication_material  SHELXL
_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)+(0.1408P)²+101.4564P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
; 
 Flack x determined using 5083 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.026(14)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         12043
_refine_ls_number_parameters     829
_refine_ls_number_restraints     172
_refine_ls_R_factor_all          0.0773
_refine_ls_R_factor_gt           0.0735
_refine_ls_wR_factor_ref         0.2060
_refine_ls_wR_factor_gt          0.2004
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.057
_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 0.39566(8) 0.4161(2) 0.8899(2) 0.0443(10) Uani 1 1 d . . . . .
O2 O 0.25483(7) 0.5080(3) 0.1947(2) 0.0467(11) Uani 1 1 d . . . . .
O3 O 0.34812(8) 0.9864(2) 0.1108(2) 0.0401(10) Uani 1 1 d . . . . .
N1 N 0.48446(8) 0.4463(2) 0.55736(19) 0.0258(9) Uani 1 1 d . . . . .
N2 N 0.41591(8) 0.5274(2) 0.2491(2) 0.0267(9) Uani 1 1 d . . . . .
N3 N 0.43852(7) 0.6492(2) 0.2382(2) 0.0255(9) Uani 1 1 d . . . . .
N4 N 0.42726(9) 0.4191(3) 0.7950(2) 0.0351(11) Uani 1 1 d . . . . .
N5 N 0.30397(9) 0.5295(3) 0.1984(3) 0.0411(12) Uani 1 1 d . . . . .
N6 N 0.36940(8) 0.8627(2) 0.1241(2) 0.0316(10) Uani 1 1 d . . . . .
C1 C 0.49026(8) 0.4417(2) 0.3405(2) 0.0208(9) Uani 1 1 d . . . . .
H1 H 0.482914 0.397321 0.340404 0.025 Uiso 1 1 calc R U . . .
C2 C 0.47455(9) 0.4931(2) 0.3114(2) 0.0217(9) Uani 1 1 d . . . . .
C3 C 0.45173(9) 0.4824(3) 0.2905(2) 0.0238(10) Uani 1 1 d . . . . .
H3 H 0.444746 0.440270 0.291990 0.029 Uiso 1 1 calc R U . . .
C4 C 0.43887(9) 0.5358(3) 0.2668(2) 0.0251(10) Uani 1 1 d . . . . .
C5 C 0.40424(9) 0.5786(3) 0.2268(2) 0.0255(10) Uani 1 1 d . . . . .
C6 C 0.41621(9) 0.6396(2) 0.2185(2) 0.0238(10) Uani 1 1 d . . . . .
C7 C 0.44996(9) 0.5983(2) 0.2632(2) 0.0241(10) Uani 1 1 d . . . . .
C8 C 0.47340(9) 0.6069(2) 0.2858(2) 0.0227(9) Uani 1 1 d . . . . .
H8 H 0.480868 0.648380 0.283790 0.027 Uiso 1 1 calc R U . . .
C9 C 0.48531(8) 0.5557(2) 0.3104(2) 0.0213(9) Uani 1 1 d . . . . .
C10 C 0.49449(8) 0.4689(2) 0.4020(2) 0.0205(9) Uani 1 1 d . . . . .
C11 C 0.48794(8) 0.4395(2) 0.4529(2) 0.0239(10) Uani 1 1 d . . . . .
H11 H 0.479910 0.398741 0.452423 0.029 Uiso 1 1 calc R U . . .
C12 C 0.49320(8) 0.4703(2) 0.5062(2) 0.0221(9) Uani 1 1 d . . . . .
C13 C 0.49097(9) 0.4752(3) 0.6066(2) 0.0281(11) Uani 1 1 d . . . . .
C14 C 0.47708(10) 0.4576(3) 0.6594(2) 0.0286(11) Uani 1 1 d . . . . .
C15 C 0.46829(10) 0.3945(3) 0.6681(3) 0.0314(11) Uani 1 1 d . . . . .
H15 H 0.473145 0.360437 0.642683 0.038 Uiso 1 1 calc R U . . .
C16 C 0.45256(11) 0.3814(3) 0.7134(3) 0.0336(12) Uani 1 1 d . . . . .
H16 H 0.446991 0.338267 0.719603 0.040 Uiso 1 1 calc R U . . .
C17 C 0.44498(10) 0.4311(3) 0.7496(2) 0.0320(11) Uani 1 1 d . . . . .
C18 C 0.45418(11) 0.4935(3) 0.7430(3) 0.0373(13) Uani 1 1 d . . . . .
H18 H 0.449464 0.527245 0.768908 0.045 Uiso 1 1 calc R U . . .
C19 C 0.47024(11) 0.5061(3) 0.6985(3) 0.0354(12) Uani 1 1 d . . . . .
H19 H 0.476747 0.548564 0.694519 0.042 Uiso 1 1 calc R U . . .
C20 C 0.43574(10) 0.4022(3) 0.8510(2) 0.0296(11) Uani 1 1 d . . . . .
C21 C 0.45959(12) 0.3858(3) 0.8627(3) 0.0378(13) Uani 1 1 d . . . . .
H21 H 0.471017 0.385418 0.831920 0.045 Uiso 1 1 calc R U . . .
C22 C 0.46665(12) 0.3702(3) 0.9187(3) 0.0416(14) Uani 1 1 d . . . . .
H22 H 0.482893 0.358706 0.925995 0.050 Uiso 1 1 calc R U . . .
C23 C 0.45061(14) 0.3710(4) 0.9640(3) 0.0469(15) Uani 1 1 d . . . . .
H23 H 0.455787 0.360523 1.002335 0.056 Uiso 1 1 calc R U . . .
C24 C 0.42684(13) 0.3870(3) 0.9538(3) 0.0434(15) Uani 1 1 d . . . . .
H24 H 0.415608 0.387784 0.984969 0.052 Uiso 1 1 calc R U . . .
C25 C 0.41963(11) 0.4020(3) 0.8973(3) 0.0338(12) Uani 1 1 d . . . . .
C26 C 0.39009(11) 0.4518(3) 0.8405(3) 0.0390(13) Uani 1 1 d . . . . .
C27 C 0.36866(12) 0.4845(4) 0.8407(3) 0.0502(16) Uani 1 1 d . . . . .
H27 H 0.358631 0.483556 0.874145 0.060 Uiso 1 1 calc R U . . .
C28 C 0.36173(14) 0.5191(5) 0.7915(4) 0.060(2) Uani 1 1 d . . . . .
H28 H 0.346755 0.541203 0.791327 0.073 Uiso 1 1 calc R U . . .
C29 C 0.37600(14) 0.5218(4) 0.7439(3) 0.0516(17) Uani 1 1 d . . . . .
H29 H 0.371021 0.545734 0.710635 0.062 Uiso 1 1 calc R U . . .
C30 C 0.39799(12) 0.4895(4) 0.7436(3) 0.0428(14) Uani 1 1 d . . . . .
H30 H 0.407953 0.491717 0.710006 0.051 Uiso 1 1 calc R U . . .
C31 C 0.40548(10) 0.4540(3) 0.7921(3) 0.0342(12) Uani 1 1 d . . . . .
C32 C 0.37823(9) 0.5687(3) 0.2144(2) 0.0275(10) Uani 1 1 d . . . . .
C33 C 0.37047(10) 0.5058(3) 0.1980(3) 0.0356(12) Uani 1 1 d . . . . .
H33 H 0.381866 0.472106 0.191783 0.043 Uiso 1 1 calc R U . . .
C34 C 0.34592(11) 0.4932(3) 0.1911(3) 0.0422(14) Uani 1 1 d . . . . .
H34 H 0.340622 0.451292 0.179171 0.051 Uiso 1 1 calc R U . . .
C35 C 0.32940(10) 0.5422(3) 0.2017(3) 0.0361(13) Uani 1 1 d . . . . .
C36 C 0.33686(10) 0.6041(3) 0.2162(3) 0.0347(12) Uani 1 1 d . . . . .
H36 H 0.325436 0.638040 0.220882 0.042 Uiso 1 1 calc R U . . .
C37 C 0.36127(10) 0.6168(3) 0.2239(3) 0.0316(11) Uani 1 1 d . . . . .
H37 H 0.366308 0.658875 0.235923 0.038 Uiso 1 1 calc R U . . .
C38 C 0.29227(10) 0.5089(3) 0.2491(3) 0.0362(13) Uani 1 1 d . . . . .
C39 C 0.30354(11) 0.4984(3) 0.3020(3) 0.0407(14) Uani 1 1 d . . . . .
H39 H 0.320322 0.505711 0.305221 0.049 Uiso 1 1 calc R U . . .
C40 C 0.29091(13) 0.4773(4) 0.3505(3) 0.0495(16) Uani 1 1 d . . . . .
H40 H 0.298948 0.470649 0.386518 0.059 Uiso 1 1 calc R U . . .
C41 C 0.26612(13) 0.4657(4) 0.3460(4) 0.0516(17) Uani 1 1 d . . . . .
H41 H 0.257307 0.451112 0.378945 0.062 Uiso 1 1 calc R U . . .
C42 C 0.25482(12) 0.4757(4) 0.2941(4) 0.0487(16) Uani 1 1 d . . . . .
H42 H 0.238051 0.467907 0.291283 0.058 Uiso 1 1 calc R U . . .
C43 C 0.26721(10) 0.4967(3) 0.2457(3) 0.0378(13) Uani 1 1 d . . . . .
C44 C 0.26788(10) 0.5102(3) 0.1437(3) 0.0383(13) Uani 1 1 d . . . . .
C45 C 0.25589(11) 0.5011(3) 0.0914(3) 0.0449(15) Uani 1 1 d . . . . .
H45 H 0.239228 0.491254 0.091594 0.054 Uiso 1 1 calc R U . . .
C46 C 0.26784(14) 0.5062(4) 0.0394(4) 0.059(2) Uani 1 1 d . . . . .
H46 H 0.259560 0.499921 0.003659 0.071 Uiso 1 1 calc R U . . .
C47 C 0.29239(14) 0.5207(5) 0.0396(4) 0.058(2) Uani 1 1 d . . . . .
H47 H 0.300774 0.525008 0.003697 0.070 Uiso 1 1 calc R U . . .
C48 C 0.30446(13) 0.5288(4) 0.0917(4) 0.0532(18) Uani 1 1 d . . . . .
H48 H 0.321099 0.538791 0.091233 0.064 Uiso 1 1 calc R U . . .
C49 C 0.29277(11) 0.5226(3) 0.1445(3) 0.0360(12) Uani 1 1 d . . . . .
C50 C 0.40480(8) 0.6972(2) 0.1912(2) 0.0243(10) Uani 1 1 d . . . . .
C51 C 0.39295(10) 0.6939(3) 0.1377(2) 0.0289(11) Uani 1 1 d . . . . .
H51 H 0.392690 0.654024 0.116705 0.035 Uiso 1 1 calc R U . . .
C52 C 0.38151(10) 0.7483(3) 0.1146(3) 0.0302(11) Uani 1 1 d . . . . .
H52 H 0.373742 0.745944 0.077769 0.036 Uiso 1 1 calc R U . . .
C53 C 0.38158(9) 0.8061(3) 0.1458(2) 0.0285(11) Uani 1 1 d . . . . .
C54 C 0.39373(10) 0.8106(3) 0.1992(3) 0.0302(11) Uani 1 1 d . . . . .
H54 H 0.393901 0.850362 0.220257 0.036 Uiso 1 1 calc R U . . .
C55 C 0.40548(9) 0.7564(3) 0.2209(2) 0.0293(11) Uani 1 1 d . . . . .
H55 H 0.414132 0.759528 0.256443 0.035 Uiso 1 1 calc R U . . .
C56 C 0.34558(9) 0.8742(3) 0.1428(2) 0.0298(11) Uani 1 1 d . . . . .
C57 C 0.33143(11) 0.8257(3) 0.1674(3) 0.0370(13) Uani 1 1 d . . . . .
H57 H 0.337804 0.783165 0.172419 0.044 Uiso 1 1 calc R U . . .
C58 C 0.30788(12) 0.8390(4) 0.1849(4) 0.0478(16) Uani 1 1 d . . . . .
H58 H 0.298281 0.805511 0.201399 0.057 Uiso 1 1 calc R U . . .
C59 C 0.29864(11) 0.9005(4) 0.1782(3) 0.0468(16) Uani 1 1 d . . . . .
H59 H 0.282665 0.909361 0.190325 0.056 Uiso 1 1 calc R U . . .
C60 C 0.31232(11) 0.9495(3) 0.1541(3) 0.0428(14) Uani 1 1 d . . . . .
H60 H 0.305904 0.992065 0.149874 0.051 Uiso 1 1 calc R U . . .
C61 C 0.33561(10) 0.9360(3) 0.1361(3) 0.0330(12) Uani 1 1 d . . . . .
C62 C 0.37261(11) 0.9778(3) 0.1012(3) 0.0333(12) Uani 1 1 d . . . . .
C63 C 0.38534(13) 1.0311(3) 0.0823(3) 0.0427(14) Uani 1 1 d . . . . .
H63 H 0.377428 1.071613 0.076890 0.051 Uiso 1 1 calc R U . . .
C64 C 0.40964(13) 1.0258(4) 0.0711(3) 0.0463(16) Uani 1 1 d . . . . .
H64 H 0.418449 1.062360 0.057516 0.056 Uiso 1 1 calc R U . . .
C65 C 0.42106(11) 0.9666(4) 0.0799(3) 0.0411(14) Uani 1 1 d . . . . .
H65 H 0.437753 0.962571 0.072357 0.049 Uiso 1 1 calc R U . . .
C66 C 0.40812(10) 0.9132(3) 0.0998(3) 0.0342(12) Uani 1 1 d . . . . .
H66 H 0.416153 0.873229 0.106909 0.041 Uiso 1 1 calc R U . . .
C67 C 0.38343(10) 0.9178(3) 0.1095(2) 0.0307(11) Uani 1 1 d . . . . .
C68 C 0.44208(16) 0.6811(4) 0.6114(4) 0.066(2) Uani 1 1 d D U . . .
H68 H 0.429856 0.675507 0.579870 0.079 Uiso 1 1 calc R U . . .
Cl1 Cl 0.43031(5) 0.64714(13) 0.67599(12) 0.0779(7) Uani 1 1 d D U . . .
Cl2 Cl 0.46799(5) 0.64096(12) 0.59004(12) 0.0741(6) Uani 1 1 d D U . . .
Cl3 Cl 0.44677(4) 0.76511(11) 0.62135(10) 0.0651(5) Uani 1 1 d D U . . .
C69 C 0.45636(19) 0.5556(6) 0.9101(6) 0.100(3) Uani 1 1 d D U . . .
H69 H 0.456323 0.507189 0.914900 0.120 Uiso 1 1 calc R U . . .
Cl4 Cl 0.47848(12) 0.5743(5) 0.8611(3) 0.245(5) Uani 1 1 d D U . . .
Cl5 Cl 0.46259(10) 0.5884(3) 0.9767(2) 0.1380(17) Uani 1 1 d D U . . .
Cl6 Cl 0.42820(9) 0.5778(2) 0.8836(2) 0.1370(17) Uani 1 1 d D U . . .
C70 C 0.3777(3) 0.5232(8) 0.0100(13) 0.166(8) Uani 1 1 d D U . . .
H70 H 0.382116 0.512002 -0.031008 0.199 Uiso 1 1 calc R U . . .
Cl7 Cl 0.36494(7) 0.45371(19) 0.03209(18) 0.1096(11) Uani 1 1 d D U . . .
Cl8 Cl 0.40306(8) 0.5460(4) 0.0353(4) 0.214(4) Uani 1 1 d D U . . .
Cl9 Cl 0.35691(12) 0.5860(3) -0.0013(4) 0.191(3) Uani 1 1 d D U . . .
C71 C 0.4527(3) 0.4710(7) 0.1054(14) 0.105(7) Uani 0.5 1 d D U P . .
H71 H 0.451306 0.472114 0.061927 0.126 Uiso 0.5 1 calc R U P . .
Cl10 Cl 0.45452(13) 0.5513(3) 0.1212(2) 0.0911(17) Uani 0.5 1 d D U P . .
Cl11 Cl 0.42880(16) 0.4293(3) 0.1230(4) 0.117(3) Uani 0.5 1 d D U P . .
Cl12 Cl 0.47859(19) 0.4295(5) 0.1141(9) 0.200(7) Uani 0.5 1 d D U P . .


_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 C25 1.377(8) . ?
O1 C26 1.385(8) . ?
O2 C43 1.377(8) . ?
O2 C44 1.378(9) . ?
O3 C61 1.376(8) . ?
O3 C62 1.394(7) . ?
N1 C13 1.326(7) . ?
N1 C12 1.363(7) . ?
N2 C5 1.338(7) . ?
N2 C4 1.353(7) . ?
N3 C6 1.337(6) . ?
N3 C7 1.354(7) . ?
N4 C20 1.411(8) . ?
N4 C31 1.411(8) . ?
N4 C17 1.456(7) . ?
N5 C49 1.393(8) . ?
N5 C38 1.397(9) . ?
N5 C35 1.443(7) . ?
N6 C56 1.415(7) . ?
N6 C67 1.416(7) . ?
N6 C53 1.437(7) . ?
C1 C2 1.525(7) . ?
C1 C9 1.527(6) 2_665 ?
C1 C10 1.535(7) . ?
C1 H1 1.0000 . ?
C2 C3 1.376(7) . ?
C2 C9 1.419(7) . ?
C3 C4 1.419(7) . ?
C3 H3 0.9500 . ?
C4 C7 1.426(7) . ?
C5 C6 1.432(7) . ?
C5 C32 1.491(7) . ?
C6 C50 1.483(7) . ?
C7 C8 1.416(7) . ?
C8 C9 1.365(7) . ?
C8 H8 0.9500 . ?
C10 C11 1.364(7) . ?
C10 C10 1.419(9) 2_665 ?
C11 C12 1.406(7) . ?
C11 H11 0.9500 . ?
C12 C12 1.437(10) 2_665 ?
C13 C13 1.433(11) 2_665 ?
C13 C14 1.483(7) . ?
C14 C19 1.393(8) . ?
C14 C15 1.400(8) . ?
C15 C16 1.387(8) . ?
C15 H15 0.9500 . ?
C16 C17 1.382(9) . ?
C16 H16 0.9500 . ?
C17 C18 1.389(9) . ?
C18 C19 1.382(8) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C20 C25 1.390(8) . ?
C20 C21 1.397(9) . ?
C21 C22 1.382(10) . ?
C21 H21 0.9500 . ?
C22 C23 1.370(10) . ?
C22 H22 0.9500 . ?
C23 C24 1.385(11) . ?
C23 H23 0.9500 . ?
C24 C25 1.392(10) . ?
C24 H24 0.9500 . ?
C26 C27 1.370(10) . ?
C26 C31 1.403(8) . ?
C27 C28 1.386(12) . ?
C27 H27 0.9500 . ?
C28 C29 1.351(11) . ?
C28 H28 0.9500 . ?
C29 C30 1.393(10) . ?
C29 H29 0.9500 . ?
C30 C31 1.396(9) . ?
C30 H30 0.9500 . ?
C32 C37 1.385(8) . ?
C32 C33 1.413(8) . ?
C33 C34 1.401(8) . ?
C33 H33 0.9500 . ?
C34 C35 1.386(9) . ?
C34 H34 0.9500 . ?
C35 C36 1.379(9) . ?
C36 C37 1.396(8) . ?
C36 H36 0.9500 . ?
C37 H37 0.9500 . ?
C38 C39 1.385(9) . ?
C38 C43 1.421(8) . ?
C39 C40 1.384(10) . ?
C39 H39 0.9500 . ?
C40 C41 1.405(10) . ?
C40 H40 0.9500 . ?
C41 C42 1.361(11) . ?
C41 H41 0.9500 . ?
C42 C43 1.377(10) . ?
C42 H42 0.9500 . ?
C44 C45 1.386(10) . ?
C44 C49 1.410(8) . ?
C45 C46 1.369(12) . ?
C45 H45 0.9500 . ?
C46 C47 1.400(12) . ?
C46 H46 0.9500 . ?
C47 C48 1.382(11) . ?
C47 H47 0.9500 . ?
C48 C49 1.380(10) . ?
C48 H48 0.9500 . ?
C50 C55 1.393(8) . ?
C50 C51 1.396(7) . ?
C51 C52 1.392(8) . ?
C51 H51 0.9500 . ?
C52 C53 1.386(8) . ?
C52 H52 0.9500 . ?
C53 C54 1.401(8) . ?
C54 C55 1.384(8) . ?
C54 H54 0.9500 . ?
C55 H55 0.9500 . ?
C56 C57 1.391(9) . ?
C56 C61 1.394(8) . ?
C57 C58 1.399(9) . ?
C57 H57 0.9500 . ?
C58 C59 1.373(10) . ?
C58 H58 0.9500 . ?
C59 C60 1.379(11) . ?
C59 H59 0.9500 . ?
C60 C61 1.390(9) . ?
C60 H60 0.9500 . ?
C62 C63 1.376(9) . ?
C62 C67 1.385(8) . ?
C63 C64 1.382(11) . ?
C63 H63 0.9500 . ?
C64 C65 1.387(11) . ?
C64 H64 0.9500 . ?
C65 C66 1.389(9) . ?
C65 H65 0.9500 . ?
C66 C67 1.397(8) . ?
C66 H66 0.9500 . ?
C68 Cl2 1.734(9) . ?
C68 Cl3 1.760(9) . ?
C68 Cl1 1.764(10) . ?
C68 H68 1.0000 . ?
C69 Cl5 1.704(12) . ?
C69 Cl4 1.712(13) . ?
C69 Cl6 1.743(13) . ?
C69 H69 1.0000 . ?
C70 Cl8 1.597(16) . ?
C70 Cl7 1.674(14) . ?
C70 Cl9 1.753(16) . ?
C70 H70 1.0000 . ?
C71 Cl11 1.634(18) . ?
C71 Cl12 1.689(18) . ?
C71 Cl10 1.693(16) . ?
C71 H71 1.0000 . ?

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
C25 O1 C26 115.5(5) . . ?
C43 O2 C44 117.5(4) . . ?
C61 O3 C62 117.8(4) . . ?
C13 N1 C12 118.2(4) . . ?
C5 N2 C4 118.3(4) . . ?
C6 N3 C7 117.8(4) . . ?
C20 N4 C31 117.1(5) . . ?
C20 N4 C17 117.7(5) . . ?
C31 N4 C17 117.6(5) . . ?
C49 N5 C38 119.9(5) . . ?
C49 N5 C35 120.3(5) . . ?
C38 N5 C35 118.1(5) . . ?
C56 N6 C67 117.2(5) . . ?
C56 N6 C53 118.2(5) . . ?
C67 N6 C53 118.0(4) . . ?
C2 C1 C9 106.8(4) . 2_665 ?
C2 C1 C10 103.8(4) . . ?
C9 C1 C10 105.4(4) 2_665 . ?
C2 C1 H1 113.3 . . ?
C9 C1 H1 113.3 2_665 . ?
C10 C1 H1 113.3 . . ?
C3 C2 C9 121.9(4) . . ?
C3 C2 C1 124.9(5) . . ?
C9 C2 C1 113.1(4) . . ?
C2 C3 C4 118.4(5) . . ?
C2 C3 H3 120.8 . . ?
C4 C3 H3 120.8 . . ?
N2 C4 C3 119.6(5) . . ?
N2 C4 C7 120.5(5) . . ?
C3 C4 C7 119.9(4) . . ?
N2 C5 C6 120.8(4) . . ?
N2 C5 C32 116.0(5) . . ?
C6 C5 C32 123.2(5) . . ?
N3 C6 C5 121.2(4) . . ?
N3 C6 C50 115.0(4) . . ?
C5 C6 C50 123.7(4) . . ?
N3 C7 C8 119.5(5) . . ?
N3 C7 C4 121.1(5) . . ?
C8 C7 C4 119.4(4) . . ?
C9 C8 C7 120.2(4) . . ?
C9 C8 H8 119.9 . . ?
C7 C8 H8 119.9 . . ?
C8 C9 C2 120.0(4) . . ?
C8 C9 C1 126.4(5) . 2_665 ?
C2 C9 C1 113.6(4) . 2_665 ?
C11 C10 C10 120.9(3) . 2_665 ?
C11 C10 C1 125.8(4) . . ?
C10 C10 C1 113.2(3) 2_665 . ?
C10 C11 C12 119.3(5) . . ?
C10 C11 H11 120.4 . . ?
C12 C11 H11 120.4 . . ?
N1 C12 C11 120.7(4) . . ?
N1 C12 C12 119.7(3) . 2_665 ?
C11 C12 C12 119.5(3) . 2_665 ?
N1 C13 C13 120.7(3) . 2_665 ?
N1 C13 C14 116.4(5) . . ?
C13 C13 C14 122.7(3) 2_665 . ?
C19 C14 C15 118.4(5) . . ?
C19 C14 C13 119.6(5) . . ?
C15 C14 C13 121.6(5) . . ?
C16 C15 C14 120.5(5) . . ?
C16 C15 H15 119.8 . . ?
C14 C15 H15 119.8 . . ?
C17 C16 C15 120.0(5) . . ?
C17 C16 H16 120.0 . . ?
C15 C16 H16 120.0 . . ?
C16 C17 C18 120.2(5) . . ?
C16 C17 N4 120.8(5) . . ?
C18 C17 N4 119.0(5) . . ?
C19 C18 C17 119.5(5) . . ?
C19 C18 H18 120.3 . . ?
C17 C18 H18 120.3 . . ?
C18 C19 C14 121.3(5) . . ?
C18 C19 H19 119.4 . . ?
C14 C19 H19 119.4 . . ?
C25 C20 C21 117.9(5) . . ?
C25 C20 N4 118.6(5) . . ?
C21 C20 N4 123.5(5) . . ?
C22 C21 C20 120.3(6) . . ?
C22 C21 H21 119.8 . . ?
C20 C21 H21 119.8 . . ?
C23 C22 C21 121.1(6) . . ?
C23 C22 H22 119.5 . . ?
C21 C22 H22 119.5 . . ?
C22 C23 C24 119.9(6) . . ?
C22 C23 H23 120.0 . . ?
C24 C23 H23 120.0 . . ?
C23 C24 C25 119.1(6) . . ?
C23 C24 H24 120.5 . . ?
C25 C24 H24 120.5 . . ?
O1 C25 C20 122.1(5) . . ?
O1 C25 C24 116.2(5) . . ?
C20 C25 C24 121.7(6) . . ?
C27 C26 O1 117.0(6) . . ?
C27 C26 C31 121.3(6) . . ?
O1 C26 C31 121.8(6) . . ?
C26 C27 C28 119.5(6) . . ?
C26 C27 H27 120.3 . . ?
C28 C27 H27 120.3 . . ?
C29 C28 C27 120.9(7) . . ?
C29 C28 H28 119.6 . . ?
C27 C28 H28 119.6 . . ?
C28 C29 C30 120.2(7) . . ?
C28 C29 H29 119.9 . . ?
C30 C29 H29 119.9 . . ?
C29 C30 C31 120.5(6) . . ?
C29 C30 H30 119.8 . . ?
C31 C30 H30 119.8 . . ?
C30 C31 C26 117.7(6) . . ?
C30 C31 N4 124.1(5) . . ?
C26 C31 N4 118.2(5) . . ?
C37 C32 C33 119.1(5) . . ?
C37 C32 C5 122.3(5) . . ?
C33 C32 C5 118.3(5) . . ?
C34 C33 C32 119.8(5) . . ?
C34 C33 H33 120.1 . . ?
C32 C33 H33 120.1 . . ?
C35 C34 C33 119.6(6) . . ?
C35 C34 H34 120.2 . . ?
C33 C34 H34 120.2 . . ?
C36 C35 C34 120.9(5) . . ?
C36 C35 N5 118.4(5) . . ?
C34 C35 N5 120.7(6) . . ?
C35 C36 C37 119.8(5) . . ?
C35 C36 H36 120.1 . . ?
C37 C36 H36 120.1 . . ?
C32 C37 C36 120.8(5) . . ?
C32 C37 H37 119.6 . . ?
C36 C37 H37 119.6 . . ?
C39 C38 N5 124.4(5) . . ?
C39 C38 C43 117.7(6) . . ?
N5 C38 C43 117.9(6) . . ?
C40 C39 C38 121.5(6) . . ?
C40 C39 H39 119.3 . . ?
C38 C39 H39 119.3 . . ?
C39 C40 C41 119.6(7) . . ?
C39 C40 H40 120.2 . . ?
C41 C40 H40 120.2 . . ?
C42 C41 C40 119.6(7) . . ?
C42 C41 H41 120.2 . . ?
C40 C41 H41 120.2 . . ?
C41 C42 C43 121.3(6) . . ?
C41 C42 H42 119.4 . . ?
C43 C42 H42 119.4 . . ?
C42 C43 O2 119.1(5) . . ?
C42 C43 C38 120.3(6) . . ?
O2 C43 C38 120.5(6) . . ?
O2 C44 C45 118.4(5) . . ?
O2 C44 C49 121.0(6) . . ?
C45 C44 C49 120.6(6) . . ?
C46 C45 C44 120.6(6) . . ?
C46 C45 H45 119.7 . . ?
C44 C45 H45 119.7 . . ?
C45 C46 C47 119.3(7) . . ?
C45 C46 H46 120.3 . . ?
C47 C46 H46 120.3 . . ?
C48 C47 C46 120.2(8) . . ?
C48 C47 H47 119.9 . . ?
C46 C47 H47 119.9 . . ?
C49 C48 C47 121.2(7) . . ?
C49 C48 H48 119.4 . . ?
C47 C48 H48 119.4 . . ?
C48 C49 N5 123.9(6) . . ?
C48 C49 C44 118.0(6) . . ?
N5 C49 C44 118.0(6) . . ?
C55 C50 C51 119.0(5) . . ?
C55 C50 C6 118.6(5) . . ?
C51 C50 C6 122.4(5) . . ?
C52 C51 C50 120.8(5) . . ?
C52 C51 H51 119.6 . . ?
C50 C51 H51 119.6 . . ?
C53 C52 C51 119.3(5) . . ?
C53 C52 H52 120.3 . . ?
C51 C52 H52 120.3 . . ?
C52 C53 C54 120.6(5) . . ?
C52 C53 N6 120.8(5) . . ?
C54 C53 N6 118.6(5) . . ?
C55 C54 C53 119.3(5) . . ?
C55 C54 H54 120.4 . . ?
C53 C54 H54 120.4 . . ?
C54 C55 C50 120.9(5) . . ?
C54 C55 H55 119.5 . . ?
C50 C55 H55 119.5 . . ?
C57 C56 C61 118.1(5) . . ?
C57 C56 N6 122.4(5) . . ?
C61 C56 N6 119.5(5) . . ?
C56 C57 C58 120.5(6) . . ?
C56 C57 H57 119.7 . . ?
C58 C57 H57 119.7 . . ?
C59 C58 C57 120.0(6) . . ?
C59 C58 H58 120.0 . . ?
C57 C58 H58 120.0 . . ?
C58 C59 C60 120.6(6) . . ?
C58 C59 H59 119.7 . . ?
C60 C59 H59 119.7 . . ?
C59 C60 C61 119.3(6) . . ?
C59 C60 H60 120.4 . . ?
C61 C60 H60 120.4 . . ?
O3 C61 C60 116.6(5) . . ?
O3 C61 C56 122.0(5) . . ?
C60 C61 C56 121.4(6) . . ?
C63 C62 C67 121.8(6) . . ?
C63 C62 O3 117.0(5) . . ?
C67 C62 O3 121.2(5) . . ?
C62 C63 C64 120.0(6) . . ?
C62 C63 H63 120.0 . . ?
C64 C63 H63 120.0 . . ?
C63 C64 C65 119.4(6) . . ?
C63 C64 H64 120.3 . . ?
C65 C64 H64 120.3 . . ?
C64 C65 C66 120.1(6) . . ?
C64 C65 H65 119.9 . . ?
C66 C65 H65 119.9 . . ?
C65 C66 C67 120.7(6) . . ?
C65 C66 H66 119.7 . . ?
C67 C66 H66 119.7 . . ?
C62 C67 C66 117.8(5) . . ?
C62 C67 N6 120.2(5) . . ?
C66 C67 N6 121.9(5) . . ?
Cl2 C68 Cl3 112.3(5) . . ?
Cl2 C68 Cl1 111.0(5) . . ?
Cl3 C68 Cl1 109.5(5) . . ?
Cl2 C68 H68 107.9 . . ?
Cl3 C68 H68 107.9 . . ?
Cl1 C68 H68 107.9 . . ?
Cl5 C69 Cl4 110.7(6) . . ?
Cl5 C69 Cl6 113.1(7) . . ?
Cl4 C69 Cl6 111.1(9) . . ?
Cl5 C69 H69 107.2 . . ?
Cl4 C69 H69 107.2 . . ?
Cl6 C69 H69 107.2 . . ?
Cl8 C70 Cl7 121.1(11) . . ?
Cl8 C70 Cl9 115.0(11) . . ?
Cl7 C70 Cl9 113.0(10) . . ?
Cl8 C70 H70 101.1 . . ?
Cl7 C70 H70 101.1 . . ?
Cl9 C70 H70 101.1 . . ?
Cl11 C71 Cl12 113.7(13) . . ?
Cl11 C71 Cl10 120.4(12) . . ?
Cl12 C71 Cl10 114.6(13) . . ?
Cl11 C71 H71 101.3 . . ?
Cl12 C71 H71 101.3 . . ?
Cl10 C71 H71 101.3 . . ?

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
C9 C1 C2 C3 130.2(5) 2_665 . . . ?
C10 C1 C2 C3 -118.7(5) . . . . ?
C9 C1 C2 C9 -53.1(5) 2_665 . . . ?
C10 C1 C2 C9 58.1(5) . . . . ?
C9 C2 C3 C4 0.7(7) . . . . ?
C1 C2 C3 C4 177.2(5) . . . . ?
C5 N2 C4 C3 -179.9(5) . . . . ?
C5 N2 C4 C7 1.7(7) . . . . ?
C2 C3 C4 N2 -176.3(5) . . . . ?
C2 C3 C4 C7 2.2(7) . . . . ?
C4 N2 C5 C6 3.9(8) . . . . ?
C4 N2 C5 C32 -173.2(5) . . . . ?
C7 N3 C6 C5 3.7(7) . . . . ?
C7 N3 C6 C50 -179.5(4) . . . . ?
N2 C5 C6 N3 -6.9(8) . . . . ?
C32 C5 C6 N3 170.0(5) . . . . ?
N2 C5 C6 C50 176.6(5) . . . . ?
C32 C5 C6 C50 -6.5(8) . . . . ?
C6 N3 C7 C8 -178.5(5) . . . . ?
C6 N3 C7 C4 2.0(7) . . . . ?
N2 C4 C7 N3 -4.9(8) . . . . ?
C3 C4 C7 N3 176.7(5) . . . . ?
N2 C4 C7 C8 175.6(5) . . . . ?
C3 C4 C7 C8 -2.8(7) . . . . ?
N3 C7 C8 C9 -179.0(5) . . . . ?
C4 C7 C8 C9 0.5(8) . . . . ?
C7 C8 C9 C2 2.4(8) . . . . ?
C7 C8 C9 C1 -175.1(5) . . . 2_665 ?
C3 C2 C9 C8 -3.1(7) . . . . ?
C1 C2 C9 C8 -179.9(4) . . . . ?
C3 C2 C9 C1 174.8(4) . . . 2_665 ?
C1 C2 C9 C1 -2.1(5) . . . 2_665 ?
C2 C1 C10 C11 119.4(5) . . . . ?
C9 C1 C10 C11 -128.4(5) 2_665 . . . ?
C2 C1 C10 C10 -58.2(6) . . . 2_665 ?
C9 C1 C10 C10 53.9(6) 2_665 . . 2_665 ?
C10 C10 C11 C12 -2.9(8) 2_665 . . . ?
C1 C10 C11 C12 179.6(4) . . . . ?
C13 N1 C12 C11 176.6(5) . . . . ?
C13 N1 C12 C12 -6.9(8) . . . 2_665 ?
C10 C11 C12 N1 172.2(4) . . . . ?
C10 C11 C12 C12 -4.3(8) . . . 2_665 ?
C12 N1 C13 C13 -7.9(9) . . . 2_665 ?
C12 N1 C13 C14 166.8(5) . . . . ?
N1 C13 C14 C19 -137.5(6) . . . . ?
C13 C13 C14 C19 37.1(9) 2_665 . . . ?
N1 C13 C14 C15 35.3(7) . . . . ?
C13 C13 C14 C15 -150.1(6) 2_665 . . . ?
C19 C14 C15 C16 2.1(8) . . . . ?
C13 C14 C15 C16 -170.8(5) . . . . ?
C14 C15 C16 C17 1.6(9) . . . . ?
C15 C16 C17 C18 -3.9(9) . . . . ?
C15 C16 C17 N4 175.9(5) . . . . ?
C20 N4 C17 C16 91.8(7) . . . . ?
C31 N4 C17 C16 -119.3(6) . . . . ?
C20 N4 C17 C18 -88.3(7) . . . . ?
C31 N4 C17 C18 60.6(7) . . . . ?
C16 C17 C18 C19 2.6(9) . . . . ?
N4 C17 C18 C19 -177.3(6) . . . . ?
C17 C18 C19 C14 1.2(10) . . . . ?
C15 C14 C19 C18 -3.4(9) . . . . ?
C13 C14 C19 C18 169.6(6) . . . . ?
C31 N4 C20 C25 19.5(8) . . . . ?
C17 N4 C20 C25 168.6(5) . . . . ?
C31 N4 C20 C21 -160.1(6) . . . . ?
C17 N4 C20 C21 -11.1(8) . . . . ?
C25 C20 C21 C22 -0.1(9) . . . . ?
N4 C20 C21 C22 179.6(6) . . . . ?
C20 C21 C22 C23 -0.6(10) . . . . ?
C21 C22 C23 C24 0.6(11) . . . . ?
C22 C23 C24 C25 0.2(11) . . . . ?
C26 O1 C25 C20 -21.9(8) . . . . ?
C26 O1 C25 C24 158.5(6) . . . . ?
C21 C20 C25 O1 -178.6(5) . . . . ?
N4 C20 C25 O1 1.7(8) . . . . ?
C21 C20 C25 C24 0.9(9) . . . . ?
N4 C20 C25 C24 -178.8(6) . . . . ?
C23 C24 C25 O1 178.6(6) . . . . ?
C23 C24 C25 C20 -1.0(10) . . . . ?
C25 O1 C26 C27 -159.4(6) . . . . ?
C25 O1 C26 C31 21.4(9) . . . . ?
O1 C26 C27 C28 -177.6(7) . . . . ?
C31 C26 C27 C28 1.7(12) . . . . ?
C26 C27 C28 C29 -1.1(14) . . . . ?
C27 C28 C29 C30 0.1(14) . . . . ?
C28 C29 C30 C31 0.2(12) . . . . ?
C29 C30 C31 C26 0.4(10) . . . . ?
C29 C30 C31 N4 179.0(7) . . . . ?
C27 C26 C31 C30 -1.3(10) . . . . ?
O1 C26 C31 C30 177.9(6) . . . . ?
C27 C26 C31 N4 -180.0(6) . . . . ?
O1 C26 C31 N4 -0.8(9) . . . . ?
C20 N4 C31 C30 161.6(6) . . . . ?
C17 N4 C31 C30 12.5(9) . . . . ?
C20 N4 C31 C26 -19.9(8) . . . . ?
C17 N4 C31 C26 -168.9(5) . . . . ?
N2 C5 C32 C37 141.9(6) . . . . ?
C6 C5 C32 C37 -35.1(8) . . . . ?
N2 C5 C32 C33 -31.4(7) . . . . ?
C6 C5 C32 C33 151.6(5) . . . . ?
C37 C32 C33 C34 0.8(9) . . . . ?
C5 C32 C33 C34 174.3(6) . . . . ?
C32 C33 C34 C35 -1.5(10) . . . . ?
C33 C34 C35 C36 3.2(11) . . . . ?
C33 C34 C35 N5 -176.1(6) . . . . ?
C49 N5 C35 C36 105.6(7) . . . . ?
C38 N5 C35 C36 -89.7(7) . . . . ?
C49 N5 C35 C34 -75.1(9) . . . . ?
C38 N5 C35 C34 89.6(8) . . . . ?
C34 C35 C36 C37 -4.1(10) . . . . ?
N5 C35 C36 C37 175.2(6) . . . . ?
C33 C32 C37 C36 -1.6(9) . . . . ?
C5 C32 C37 C36 -174.9(5) . . . . ?
C35 C36 C37 C32 3.3(9) . . . . ?
C49 N5 C38 C39 163.2(6) . . . . ?
C35 N5 C38 C39 -1.6(9) . . . . ?
C49 N5 C38 C43 -15.4(9) . . . . ?
C35 N5 C38 C43 179.8(6) . . . . ?
N5 C38 C39 C40 -179.3(7) . . . . ?
C43 C38 C39 C40 -0.7(10) . . . . ?
C38 C39 C40 C41 0.5(11) . . . . ?
C39 C40 C41 C42 -0.2(11) . . . . ?
C40 C41 C42 C43 0.1(12) . . . . ?
C41 C42 C43 O2 -178.0(7) . . . . ?
C41 C42 C43 C38 -0.3(11) . . . . ?
C44 O2 C43 C42 -161.4(6) . . . . ?
C44 O2 C43 C38 20.9(9) . . . . ?
C39 C38 C43 C42 0.6(9) . . . . ?
N5 C38 C43 C42 179.3(6) . . . . ?
C39 C38 C43 O2 178.3(6) . . . . ?
N5 C38 C43 O2 -3.0(9) . . . . ?
C43 O2 C44 C45 160.2(6) . . . . ?
C43 O2 C44 C49 -20.9(8) . . . . ?
O2 C44 C45 C46 176.6(7) . . . . ?
C49 C44 C45 C46 -2.2(10) . . . . ?
C44 C45 C46 C47 0.0(12) . . . . ?
C45 C46 C47 C48 1.0(13) . . . . ?
C46 C47 C48 C49 0.2(13) . . . . ?
C47 C48 C49 N5 179.4(7) . . . . ?
C47 C48 C49 C44 -2.4(11) . . . . ?
C38 N5 C49 C48 -166.2(7) . . . . ?
C35 N5 C49 C48 -1.8(10) . . . . ?
C38 N5 C49 C44 15.5(9) . . . . ?
C35 N5 C49 C44 180.0(6) . . . . ?
O2 C44 C49 C48 -175.4(6) . . . . ?
C45 C44 C49 C48 3.4(10) . . . . ?
O2 C44 C49 N5 3.0(9) . . . . ?
C45 C44 C49 N5 -178.3(6) . . . . ?
N3 C6 C50 C55 -49.1(7) . . . . ?
C5 C6 C50 C55 127.6(6) . . . . ?
N3 C6 C50 C51 132.5(5) . . . . ?
C5 C6 C50 C51 -50.9(7) . . . . ?
C55 C50 C51 C52 -1.4(8) . . . . ?
C6 C50 C51 C52 177.1(5) . . . . ?
C50 C51 C52 C53 -1.2(8) . . . . ?
C51 C52 C53 C54 2.3(8) . . . . ?
C51 C52 C53 N6 -178.3(5) . . . . ?
C56 N6 C53 C52 94.1(7) . . . . ?
C67 N6 C53 C52 -115.2(6) . . . . ?
C56 N6 C53 C54 -86.4(6) . . . . ?
C67 N6 C53 C54 64.2(7) . . . . ?
C52 C53 C54 C55 -0.8(8) . . . . ?
N6 C53 C54 C55 179.8(5) . . . . ?
C53 C54 C55 C50 -1.8(8) . . . . ?
C51 C50 C55 C54 2.9(8) . . . . ?
C6 C50 C55 C54 -175.6(5) . . . . ?
C67 N6 C56 C57 -169.0(5) . . . . ?
C53 N6 C56 C57 -18.1(8) . . . . ?
C67 N6 C56 C61 11.6(8) . . . . ?
C53 N6 C56 C61 162.5(5) . . . . ?
C61 C56 C57 C58 -0.1(9) . . . . ?
N6 C56 C57 C58 -179.5(6) . . . . ?
C56 C57 C58 C59 -0.5(11) . . . . ?
C57 C58 C59 C60 0.3(12) . . . . ?
C58 C59 C60 C61 0.5(11) . . . . ?
C62 O3 C61 C60 169.5(6) . . . . ?
C62 O3 C61 C56 -11.2(8) . . . . ?
C59 C60 C61 O3 178.2(6) . . . . ?
C59 C60 C61 C56 -1.2(10) . . . . ?
C57 C56 C61 O3 -178.4(5) . . . . ?
N6 C56 C61 O3 1.1(8) . . . . ?
C57 C56 C61 C60 0.9(9) . . . . ?
N6 C56 C61 C60 -179.6(6) . . . . ?
C61 O3 C62 C63 -172.6(6) . . . . ?
C61 O3 C62 C67 8.4(8) . . . . ?
C67 C62 C63 C64 -0.1(10) . . . . ?
O3 C62 C63 C64 -179.1(6) . . . . ?
C62 C63 C64 C65 -0.9(10) . . . . ?
C63 C64 C65 C66 0.0(10) . . . . ?
C64 C65 C66 C67 1.9(10) . . . . ?
C63 C62 C67 C66 2.0(9) . . . . ?
O3 C62 C67 C66 -179.0(5) . . . . ?
C63 C62 C67 N6 -174.5(6) . . . . ?
O3 C62 C67 N6 4.4(9) . . . . ?
C65 C66 C67 C62 -2.9(9) . . . . ?
C65 C66 C67 N6 173.6(6) . . . . ?
C56 N6 C67 C62 -14.3(8) . . . . ?
C53 N6 C67 C62 -165.3(5) . . . . ?
C56 N6 C67 C66 169.3(5) . . . . ?
C53 N6 C67 C66 18.3(8) . . . . ?

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
C18 H18 Cl4 0.95 2.83 3.452(8) 123.9 . yes
C34 H34 Cl6 0.95 2.94 3.885(7) 174.7 16_544 yes
C42 H42 Cl3 0.95 2.96 3.692(7) 134.5 11_464 yes

_refine_diff_density_max         0.707
_refine_diff_density_min         -0.618
_refine_diff_density_rms         0.089


#===END
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: methanol/chloroform'
####################################################################### 
# 
# 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_1AdotCDCl3
_database_code_depnum_ccdc_archive 'CCDC 2092861'
loop_
_audit_author_name
_audit_author_address
'Mark Elsegood'
;Loughborough University
United Kingdom
;
_audit_update_record             
;
2021-06-28 deposited with the CCDC.	2022-03-24 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         'C44 H28 N4 O2, C D Cl3'
_chemical_formula_sum            'C45 H28 Cl3 D N4 O2'
_chemical_formula_weight         765.08

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0037 0.0018 '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 0.0071 0.0036 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0121 0.0066 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1567 0.1694 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
D D 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           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   10.6447(4)
_cell_length_b                   30.3665(11)
_cell_length_c                   11.1066(4)
_cell_angle_alpha                90
_cell_angle_beta                 98.9610(10)
_cell_angle_gamma                90
_cell_volume                     3546.3(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9831
_cell_measurement_theta_min      2.35
_cell_measurement_theta_max      31.39

_exptl_crystal_description       lath
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.433
_exptl_crystal_F_000             1576
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.015
_exptl_absorpt_coefficient_mu    0.323
_shelx_estimated_absorpt_T_min   0.909
_shelx_estimated_absorpt_T_max   0.995
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.702
_exptl_absorpt_correction_T_max  0.746
_exptl_absorpt_process_details   'SADABS v2016/2, Sheldrick, G.M., (2016)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.7288
_diffrn_radiation_type           synchrotron
_diffrn_source                   'Advanced Light Source station 11.3.1'
_diffrn_measurement_device_type  'Bruker D8 with PHOTON 100 detector'
_diffrn_measurement_method       'ω/θ shutterless scans'
_diffrn_detector_area_resol_mean 10.42
_diffrn_radiation_monochromator  'silicon 111'
_diffrn_reflns_number            257132
_diffrn_reflns_av_unetI/netI     0.0149
_diffrn_reflns_av_R_equivalents  0.0372
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -43
_diffrn_reflns_limit_k_max       43
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.986
_diffrn_reflns_theta_max         31.422
_diffrn_reflns_theta_full        25.930
_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 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             10853
_reflns_number_gt                10213
_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 APEX 2'
_computing_cell_refinement       'Bruker SAINT v8.38a'
_computing_data_reduction        'Bruker SAINT v8.38a'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0521P)²+2.5086P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         10853
_refine_ls_number_parameters     603
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0481
_refine_ls_R_factor_gt           0.0458
_refine_ls_wR_factor_ref         0.1238
_refine_ls_wR_factor_gt          0.1222
_refine_ls_goodness_of_fit_ref   1.111
_refine_ls_restrained_S_all      1.114
_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
N1 N 0.31970(11) 0.53523(4) 0.62188(10) 0.0197(2) Uani 1 1 d . . . . .
C1 C 0.24330(12) 0.50408(4) 0.67041(11) 0.0176(2) Uani 1 1 d . . . . .
C2 C 0.14218(12) 0.48231(5) 0.59994(12) 0.0204(2) Uani 1 1 d . . . . .
H2 H 0.1218(19) 0.4882(7) 0.5129(18) 0.027(5) Uiso 1 1 d . . . . .
C3 C 0.06764(13) 0.45230(5) 0.65257(13) 0.0222(2) Uani 1 1 d . . . . .
H3 H -0.003(2) 0.4375(7) 0.6041(19) 0.033(5) Uiso 1 1 d . . . . .
C4 C 0.09206(13) 0.44375(5) 0.77678(13) 0.0225(2) Uani 1 1 d . . . . .
H4 H 0.043(2) 0.4226(7) 0.8139(19) 0.034(5) Uiso 1 1 d . . . . .
C5 C 0.19181(13) 0.46573(5) 0.84832(12) 0.0213(2) Uani 1 1 d . . . . .
H5 H 0.211(2) 0.4630(7) 0.9387(19) 0.030(5) Uiso 1 1 d . . . . .
C6 C 0.26592(12) 0.49523(4) 0.79571(11) 0.0181(2) Uani 1 1 d . . . . .
O1 O 0.36038(9) 0.51680(4) 0.87398(8) 0.02250(19) Uani 1 1 d . . . . .
C7 C 0.44365(12) 0.54319(4) 0.82255(11) 0.0183(2) Uani 1 1 d . . . . .
C8 C 0.54672(13) 0.55963(5) 0.90117(12) 0.0217(2) Uani 1 1 d . . . . .
H8 H 0.5518(19) 0.5520(7) 0.9830(19) 0.027(5) Uiso 1 1 d . . . . .
C9 C 0.63443(14) 0.58684(5) 0.85659(13) 0.0248(3) Uani 1 1 d D . . . .
H9 H 0.7105(17) 0.6002(7) 0.9118(17) 0.034(5) Uiso 1 1 d D . . . .
C10 C 0.61746(13) 0.59727(5) 0.73361(13) 0.0244(3) Uani 1 1 d . . . . .
H10 H 0.6802(19) 0.6162(7) 0.6979(18) 0.028(5) Uiso 1 1 d . . . . .
C11 C 0.51345(13) 0.58054(4) 0.65483(12) 0.0209(2) Uani 1 1 d . . . . .
H11 H 0.5051(19) 0.5869(7) 0.5701(18) 0.027(5) Uiso 1 1 d . . . . .
C12 C 0.42452(12) 0.55337(4) 0.69791(11) 0.0174(2) Uani 1 1 d . . . . .
C13 C 0.29874(12) 0.54511(4) 0.49453(11) 0.0177(2) Uani 1 1 d . . . . .
C14 C 0.31201(12) 0.51226(4) 0.41018(11) 0.0192(2) Uani 1 1 d . . . . .
H14 H 0.3386(18) 0.4823(7) 0.4374(18) 0.025(5) Uiso 1 1 d . . . . .
C15 C 0.28879(12) 0.52156(4) 0.28577(11) 0.0188(2) Uani 1 1 d . . . . .
H15 H 0.2931(18) 0.4980(6) 0.2285(18) 0.024(4) Uiso 1 1 d . . . . .
C16 C 0.25792(11) 0.56431(4) 0.24602(11) 0.0165(2) Uani 1 1 d . . . . .
C17 C 0.24766(12) 0.59728(4) 0.33134(11) 0.0186(2) Uani 1 1 d . . . . .
H17 H 0.2260(17) 0.6264(6) 0.3087(17) 0.021(4) Uiso 1 1 d . . . . .
C18 C 0.26541(12) 0.58768(4) 0.45522(11) 0.0187(2) Uani 1 1 d . . . . .
H18 H 0.2566(18) 0.6109(6) 0.5140(18) 0.025(5) Uiso 1 1 d . . . . .
C19 C 0.23439(11) 0.57504(4) 0.11338(11) 0.0164(2) Uani 1 1 d . . . . .
N2 N 0.13714(10) 0.55515(4) 0.04721(9) 0.01758(19) Uani 1 1 d . . . . .
C20 C 0.10528(11) 0.56837(4) -0.07124(11) 0.0166(2) Uani 1 1 d . . . . .
C21 C -0.00197(12) 0.54931(4) -0.14411(12) 0.0194(2) Uani 1 1 d . . . . .
H21 H -0.0452(19) 0.5265(7) -0.1090(18) 0.028(5) Uiso 1 1 d . . . . .
C22 C -0.03820(13) 0.56415(5) -0.26118(12) 0.0211(2) Uani 1 1 d . . . . .
H22 H -0.109(2) 0.5512(7) -0.310(2) 0.032(5) Uiso 1 1 d . . . . .
C23 C 0.03045(13) 0.59784(5) -0.30974(12) 0.0219(2) Uani 1 1 d . . . . .
H23 H 0.0028(19) 0.6090(7) -0.3904(18) 0.028(5) Uiso 1 1 d . . . . .
C24 C 0.13611(13) 0.61615(4) -0.24150(11) 0.0202(2) Uani 1 1 d . . . . .
H24 H 0.1844(19) 0.6389(7) -0.2755(18) 0.030(5) Uiso 1 1 d . . . . .
C25 C 0.17556(11) 0.60166(4) -0.12036(11) 0.0163(2) Uani 1 1 d . . . . .
N3 N 0.28074(10) 0.61997(4) -0.05257(9) 0.01635(19) Uani 1 1 d . . . . .
C26 C 0.31046(11) 0.60697(4) 0.06194(11) 0.0155(2) Uani 1 1 d . . . . .
C27 C 0.42833(11) 0.62592(4) 0.13215(11) 0.0168(2) Uani 1 1 d . . . . .
C28 C 0.45655(12) 0.67033(4) 0.11740(12) 0.0201(2) Uani 1 1 d . . . . .
H28 H 0.3947(18) 0.6886(6) 0.0658(18) 0.023(4) Uiso 1 1 d . . . . .
C29 C 0.57342(13) 0.68760(5) 0.17018(13) 0.0232(3) Uani 1 1 d . . . . .
H29 H 0.5941(19) 0.7184(7) 0.1572(18) 0.027(5) Uiso 1 1 d . . . . .
C30 C 0.66288(12) 0.66021(5) 0.23748(12) 0.0234(3) Uani 1 1 d . . . . .
C31 C 0.63368(12) 0.61650(5) 0.25784(12) 0.0229(3) Uani 1 1 d . . . . .
H31 H 0.6950(19) 0.5974(6) 0.3055(18) 0.026(5) Uiso 1 1 d . . . . .
C32 C 0.51672(12) 0.59938(5) 0.20551(12) 0.0196(2) Uani 1 1 d . . . . .
H32 H 0.5014(19) 0.5689(7) 0.2168(18) 0.025(5) Uiso 1 1 d . . . . .
N4 N 0.78910(12) 0.67627(5) 0.27659(12) 0.0297(3) Uani 1 1 d . . . . .
C33 C 0.83332(14) 0.68558(5) 0.39911(13) 0.0243(3) Uani 1 1 d . . . . .
C34 C 0.75324(15) 0.68674(5) 0.48655(14) 0.0271(3) Uani 1 1 d D . . . .
H34 H 0.6663(15) 0.6804(7) 0.4655(19) 0.032(5) Uiso 1 1 d D . . . .
C35 C 0.80090(17) 0.69776(5) 0.60792(14) 0.0306(3) Uani 1 1 d . . . . .
H35 H 0.7445(19) 0.6991(7) 0.6686(18) 0.027(5) Uiso 1 1 d . . . . .
C36 C 0.92920(17) 0.70723(5) 0.64151(14) 0.0321(3) Uani 1 1 d D . . . .
H36 H 0.960(2) 0.7149(7) 0.7414(14) 0.030(5) Uiso 1 1 d D . . . .
C37 C 1.00992(16) 0.70586(5) 0.55456(14) 0.0298(3) Uani 1 1 d . . . . .
H37 H 1.102(2) 0.7125(7) 0.578(2) 0.034(5) Uiso 1 1 d . . . . .
C38 C 0.96266(14) 0.69526(5) 0.43537(14) 0.0260(3) Uani 1 1 d . . . . .
O2 O 1.04897(11) 0.69516(5) 0.35351(11) 0.0362(3) Uani 1 1 d . . . . .
C39 C 1.00269(13) 0.68703(5) 0.23205(14) 0.0248(3) Uani 1 1 d . . . . .
C40 C 1.08877(13) 0.68936(5) 0.15088(16) 0.0271(3) Uani 1 1 d . . . . .
H40 H 1.172(2) 0.6976(8) 0.182(2) 0.040(6) Uiso 1 1 d . . . . .
C41 C 1.04951(15) 0.68179(5) 0.02738(16) 0.0296(3) Uani 1 1 d . . . . .
H41 H 1.113(2) 0.6853(8) -0.030(2) 0.050(7) Uiso 1 1 d . . . . .
C42 C 0.92348(15) 0.67113(6) -0.01370(15) 0.0303(3) Uani 1 1 d . . . . .
H42 H 0.8978(16) 0.6649(5) -0.1031(15) 0.012(4) Uiso 1 1 d . . . . .
C43 C 0.83673(14) 0.66871(5) 0.06856(14) 0.0265(3) Uani 1 1 d . . . . .
H43 H 0.7478(19) 0.6610(6) 0.0388(18) 0.026(5) Uiso 1 1 d . . . . .
C44 C 0.87464(13) 0.67710(5) 0.19210(13) 0.0234(3) Uani 1 1 d . . . . .
C45 C 0.42106(15) 0.69876(5) -0.20390(15) 0.0301(3) Uani 1 1 d . . . . .
H45 H 0.4102(18) 0.6702(6) -0.1751(17) 0.022(4) Uiso 1 1 d . . . . .
Cl1 Cl 0.30307(4) 0.73389(2) -0.16194(4) 0.03909(10) Uani 1 1 d . . . . .
Cl2 Cl 0.40707(4) 0.69671(2) -0.36448(4) 0.03738(10) Uani 1 1 d . . . . .
Cl3 Cl 0.57427(4) 0.71678(2) -0.13982(4) 0.03686(10) Uani 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
N1 C12 1.4028(16) . ?
N1 C1 1.4082(16) . ?
N1 C13 1.4290(15) . ?
C1 C2 1.3950(17) . ?
C1 C6 1.4009(16) . ?
C2 C3 1.3951(19) . ?
C2 H2 0.97(2) . ?
C3 C4 1.3879(19) . ?
C3 H3 0.96(2) . ?
C4 C5 1.3933(19) . ?
C4 H4 0.96(2) . ?
C5 C6 1.3820(18) . ?
C5 H5 1.00(2) . ?
C6 O1 1.3868(15) . ?
O1 C7 1.3829(16) . ?
C7 C8 1.3846(17) . ?
C7 C12 1.4020(17) . ?
C8 C9 1.394(2) . ?
C8 H8 0.93(2) . ?
C9 C10 1.386(2) . ?
C9 H9 1.021(15) . ?
C10 C11 1.3956(18) . ?
C10 H10 1.01(2) . ?
C11 C12 1.3951(18) . ?
C11 H11 0.95(2) . ?
C13 C14 1.3906(18) . ?
C13 C18 1.3927(18) . ?
C14 C15 1.3942(17) . ?
C14 H14 0.99(2) . ?
C15 C16 1.3940(18) . ?
C15 H15 0.96(2) . ?
C16 C17 1.3944(18) . ?
C16 C19 1.4914(16) . ?
C17 C18 1.3902(17) . ?
C17 H17 0.938(19) . ?
C18 H18 0.98(2) . ?
C19 N2 1.3190(15) . ?
C19 C26 1.4375(17) . ?
N2 C20 1.3668(15) . ?
C20 C21 1.4162(16) . ?
C20 C25 1.4163(17) . ?
C21 C22 1.3733(18) . ?
C21 H21 0.95(2) . ?
C22 C23 1.4122(19) . ?
C22 H22 0.94(2) . ?
C23 C24 1.3721(18) . ?
C23 H23 0.96(2) . ?
C24 C25 1.4157(16) . ?
C24 H24 0.97(2) . ?
C25 N3 1.3664(15) . ?
N3 C26 1.3221(15) . ?
C26 C27 1.4861(16) . ?
C27 C28 1.3969(18) . ?
C27 C32 1.4000(17) . ?
C28 C29 1.3925(18) . ?
C28 H28 0.976(19) . ?
C29 C30 1.391(2) . ?
C29 H29 0.98(2) . ?
C30 C31 1.390(2) . ?
C30 N4 1.4316(17) . ?
C31 C32 1.3903(18) . ?
C31 H31 0.97(2) . ?
C32 H32 0.95(2) . ?
N4 C33 1.3977(18) . ?
N4 C44 1.4060(19) . ?
C33 C34 1.389(2) . ?
C33 C38 1.4040(19) . ?
C34 C35 1.405(2) . ?
C34 H34 0.939(15) . ?
C35 C36 1.389(2) . ?
C35 H35 0.97(2) . ?
C36 C37 1.390(3) . ?
C36 H36 1.131(15) . ?
C37 C38 1.379(2) . ?
C37 H37 0.99(2) . ?
C38 O2 1.390(2) . ?
O2 C39 1.3844(18) . ?
C39 C40 1.384(2) . ?
C39 C44 1.3990(18) . ?
C40 C41 1.389(2) . ?
C40 H40 0.93(2) . ?
C41 C42 1.386(2) . ?
C41 H41 1.00(3) . ?
C42 C43 1.399(2) . ?
C42 H42 1.006(16) . ?
C43 C44 1.392(2) . ?
C43 H43 0.98(2) . ?
C45 Cl3 1.7618(16) . ?
C45 Cl1 1.7650(18) . ?
C45 Cl2 1.7675(17) . ?
C45 H45 0.938(19) . ?

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 N1 C1 119.08(10) . . ?
C12 N1 C13 120.02(10) . . ?
C1 N1 C13 120.62(10) . . ?
C2 C1 C6 117.68(12) . . ?
C2 C1 N1 123.01(11) . . ?
C6 C1 N1 119.28(11) . . ?
C1 C2 C3 120.94(12) . . ?
C1 C2 H2 120.2(12) . . ?
C3 C2 H2 118.9(12) . . ?
C4 C3 C2 120.53(12) . . ?
C4 C3 H3 118.5(13) . . ?
C2 C3 H3 121.0(13) . . ?
C3 C4 C5 119.03(12) . . ?
C3 C4 H4 121.4(13) . . ?
C5 C4 H4 119.5(13) . . ?
C6 C5 C4 120.26(12) . . ?
C6 C5 H5 116.1(12) . . ?
C4 C5 H5 123.5(12) . . ?
C5 C6 O1 116.55(11) . . ?
C5 C6 C1 121.56(12) . . ?
O1 C6 C1 121.85(11) . . ?
C7 O1 C6 117.62(10) . . ?
O1 C7 C8 116.39(11) . . ?
O1 C7 C12 122.13(11) . . ?
C8 C7 C12 121.48(12) . . ?
C7 C8 C9 119.90(12) . . ?
C7 C8 H8 116.5(13) . . ?
C9 C8 H8 123.6(13) . . ?
C10 C9 C8 119.58(12) . . ?
C10 C9 H9 118.1(12) . . ?
C8 C9 H9 122.3(12) . . ?
C9 C10 C11 120.24(13) . . ?
C9 C10 H10 121.7(12) . . ?
C11 C10 H10 118.1(11) . . ?
C12 C11 C10 120.97(12) . . ?
C12 C11 H11 119.7(12) . . ?
C10 C11 H11 119.3(12) . . ?
C11 C12 C7 117.84(11) . . ?
C11 C12 N1 122.98(11) . . ?
C7 C12 N1 119.16(11) . . ?
C14 C13 C18 120.16(11) . . ?
C14 C13 N1 119.98(12) . . ?
C18 C13 N1 119.86(11) . . ?
C13 C14 C15 120.10(12) . . ?
C13 C14 H14 120.7(11) . . ?
C15 C14 H14 119.2(11) . . ?
C16 C15 C14 119.94(12) . . ?
C16 C15 H15 121.0(12) . . ?
C14 C15 H15 119.0(12) . . ?
C15 C16 C17 119.54(11) . . ?
C15 C16 C19 120.75(11) . . ?
C17 C16 C19 119.71(11) . . ?
C18 C17 C16 120.60(12) . . ?
C18 C17 H17 116.9(11) . . ?
C16 C17 H17 122.5(11) . . ?
C17 C18 C13 119.57(12) . . ?
C17 C18 H18 119.9(12) . . ?
C13 C18 H18 120.5(11) . . ?
N2 C19 C26 121.96(11) . . ?
N2 C19 C16 116.54(11) . . ?
C26 C19 C16 121.44(10) . . ?
C19 N2 C20 117.21(11) . . ?
N2 C20 C21 119.15(11) . . ?
N2 C20 C25 120.91(11) . . ?
C21 C20 C25 119.92(11) . . ?
C22 C21 C20 119.30(12) . . ?
C22 C21 H21 123.1(12) . . ?
C20 C21 H21 117.6(12) . . ?
C21 C22 C23 120.91(12) . . ?
C21 C22 H22 119.5(13) . . ?
C23 C22 H22 119.6(13) . . ?
C24 C23 C22 120.73(12) . . ?
C24 C23 H23 118.5(12) . . ?
C22 C23 H23 120.7(12) . . ?
C23 C24 C25 119.69(12) . . ?
C23 C24 H24 120.7(12) . . ?
C25 C24 H24 119.6(12) . . ?
N3 C25 C24 119.57(11) . . ?
N3 C25 C20 120.99(11) . . ?
C24 C25 C20 119.44(11) . . ?
C26 N3 C25 117.47(10) . . ?
N3 C26 C19 121.23(11) . . ?
N3 C26 C27 116.43(11) . . ?
C19 C26 C27 122.30(10) . . ?
C28 C27 C32 119.12(11) . . ?
C28 C27 C26 119.45(11) . . ?
C32 C27 C26 121.23(11) . . ?
C29 C28 C27 120.58(12) . . ?
C29 C28 H28 120.6(11) . . ?
C27 C28 H28 118.7(11) . . ?
C30 C29 C28 119.52(13) . . ?
C30 C29 H29 120.1(12) . . ?
C28 C29 H29 120.4(12) . . ?
C31 C30 C29 120.44(12) . . ?
C31 C30 N4 119.93(13) . . ?
C29 C30 N4 119.40(13) . . ?
C30 C31 C32 119.84(13) . . ?
C30 C31 H31 120.8(12) . . ?
C32 C31 H31 119.3(12) . . ?
C31 C32 C27 120.33(13) . . ?
C31 C32 H32 118.0(12) . . ?
C27 C32 H32 121.6(12) . . ?
C33 N4 C44 119.42(12) . . ?
C33 N4 C30 121.48(12) . . ?
C44 N4 C30 118.58(12) . . ?
C34 C33 N4 122.38(13) . . ?
C34 C33 C38 118.38(13) . . ?
N4 C33 C38 119.22(14) . . ?
C33 C34 C35 120.51(14) . . ?
C33 C34 H34 120.6(13) . . ?
C35 C34 H34 118.9(13) . . ?
C36 C35 C34 120.02(16) . . ?
C36 C35 H35 119.5(12) . . ?
C34 C35 H35 120.4(12) . . ?
C35 C36 C37 119.72(14) . . ?
C35 C36 H36 115.4(11) . . ?
C37 C36 H36 124.9(11) . . ?
C38 C37 C36 120.10(15) . . ?
C38 C37 H37 119.8(13) . . ?
C36 C37 H37 120.1(13) . . ?
C37 C38 O2 116.68(13) . . ?
C37 C38 C33 121.27(15) . . ?
O2 C38 C33 122.05(13) . . ?
C39 O2 C38 117.82(11) . . ?
C40 C39 O2 117.03(13) . . ?
C40 C39 C44 121.05(14) . . ?
O2 C39 C44 121.93(14) . . ?
C39 C40 C41 120.45(13) . . ?
C39 C40 H40 117.0(14) . . ?
C41 C40 H40 122.5(14) . . ?
C42 C41 C40 119.37(14) . . ?
C42 C41 H41 121.6(14) . . ?
C40 C41 H41 118.9(15) . . ?
C41 C42 C43 120.06(15) . . ?
C41 C42 H42 117.9(10) . . ?
C43 C42 H42 122.0(10) . . ?
C44 C43 C42 120.98(14) . . ?
C44 C43 H43 119.5(12) . . ?
C42 C43 H43 119.5(12) . . ?
C43 C44 C39 118.08(13) . . ?
C43 C44 N4 122.42(12) . . ?
C39 C44 N4 119.50(13) . . ?
Cl3 C45 Cl1 110.96(9) . . ?
Cl3 C45 Cl2 110.23(9) . . ?
Cl1 C45 Cl2 109.64(8) . . ?
Cl3 C45 H45 107.7(12) . . ?
Cl1 C45 H45 109.8(12) . . ?
Cl2 C45 H45 108.4(12) . . ?

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
C12 N1 C1 C2 -175.86(12) . . . . ?
C13 N1 C1 C2 -2.0(2) . . . . ?
C12 N1 C1 C6 6.32(18) . . . . ?
C13 N1 C1 C6 -179.78(12) . . . . ?
C6 C1 C2 C3 -0.9(2) . . . . ?
N1 C1 C2 C3 -178.79(13) . . . . ?
C1 C2 C3 C4 0.5(2) . . . . ?
C2 C3 C4 C5 0.3(2) . . . . ?
C3 C4 C5 C6 -0.7(2) . . . . ?
C4 C5 C6 O1 177.86(12) . . . . ?
C4 C5 C6 C1 0.3(2) . . . . ?
C2 C1 C6 C5 0.54(19) . . . . ?
N1 C1 C6 C5 178.47(12) . . . . ?
C2 C1 C6 O1 -176.92(12) . . . . ?
N1 C1 C6 O1 1.01(19) . . . . ?
C5 C6 O1 C7 173.84(12) . . . . ?
C1 C6 O1 C7 -8.58(18) . . . . ?
C6 O1 C7 C8 -171.74(12) . . . . ?
C6 O1 C7 C12 9.06(18) . . . . ?
O1 C7 C8 C9 -179.43(13) . . . . ?
C12 C7 C8 C9 -0.2(2) . . . . ?
C7 C8 C9 C10 0.1(2) . . . . ?
C8 C9 C10 C11 -0.2(2) . . . . ?
C9 C10 C11 C12 0.4(2) . . . . ?
C10 C11 C12 C7 -0.5(2) . . . . ?
C10 C11 C12 N1 -178.94(13) . . . . ?
O1 C7 C12 C11 179.57(12) . . . . ?
C8 C7 C12 C11 0.40(19) . . . . ?
O1 C7 C12 N1 -1.92(19) . . . . ?
C8 C7 C12 N1 178.92(12) . . . . ?
C1 N1 C12 C11 172.55(12) . . . . ?
C13 N1 C12 C11 -1.4(2) . . . . ?
C1 N1 C12 C7 -5.89(18) . . . . ?
C13 N1 C12 C7 -179.83(12) . . . . ?
C12 N1 C13 C14 112.12(14) . . . . ?
C1 N1 C13 C14 -61.72(17) . . . . ?
C12 N1 C13 C18 -67.69(17) . . . . ?
C1 N1 C13 C18 118.47(14) . . . . ?
C18 C13 C14 C15 -1.66(19) . . . . ?
N1 C13 C14 C15 178.53(11) . . . . ?
C13 C14 C15 C16 2.95(19) . . . . ?
C14 C15 C16 C17 -1.47(19) . . . . ?
C14 C15 C16 C19 179.20(11) . . . . ?
C15 C16 C17 C18 -1.29(19) . . . . ?
C19 C16 C17 C18 178.04(11) . . . . ?
C16 C17 C18 C13 2.58(19) . . . . ?
C14 C13 C18 C17 -1.10(19) . . . . ?
N1 C13 C18 C17 178.71(11) . . . . ?
C15 C16 C19 N2 62.69(16) . . . . ?
C17 C16 C19 N2 -116.63(13) . . . . ?
C15 C16 C19 C26 -120.11(14) . . . . ?
C17 C16 C19 C26 60.57(16) . . . . ?
C26 C19 N2 C20 -4.58(18) . . . . ?
C16 C19 N2 C20 172.60(11) . . . . ?
C19 N2 C20 C21 -177.21(12) . . . . ?
C19 N2 C20 C25 0.85(18) . . . . ?
N2 C20 C21 C22 176.62(12) . . . . ?
C25 C20 C21 C22 -1.46(19) . . . . ?
C20 C21 C22 C23 0.4(2) . . . . ?
C21 C22 C23 C24 0.9(2) . . . . ?
C22 C23 C24 C25 -1.1(2) . . . . ?
C23 C24 C25 N3 -179.94(12) . . . . ?
C23 C24 C25 C20 0.0(2) . . . . ?
N2 C20 C25 N3 3.17(19) . . . . ?
C21 C20 C25 N3 -178.79(12) . . . . ?
N2 C20 C25 C24 -176.81(12) . . . . ?
C21 C20 C25 C24 1.24(19) . . . . ?
C24 C25 N3 C26 176.78(12) . . . . ?
C20 C25 N3 C26 -3.20(18) . . . . ?
C25 N3 C26 C19 -0.47(18) . . . . ?
C25 N3 C26 C27 177.44(11) . . . . ?
N2 C19 C26 N3 4.62(19) . . . . ?
C16 C19 C26 N3 -172.43(11) . . . . ?
N2 C19 C26 C27 -173.17(12) . . . . ?
C16 C19 C26 C27 9.78(18) . . . . ?
N3 C26 C27 C28 40.12(17) . . . . ?
C19 C26 C27 C28 -141.99(13) . . . . ?
N3 C26 C27 C32 -134.78(13) . . . . ?
C19 C26 C27 C32 43.11(18) . . . . ?
C32 C27 C28 C29 2.98(19) . . . . ?
C26 C27 C28 C29 -172.03(12) . . . . ?
C27 C28 C29 C30 0.4(2) . . . . ?
C28 C29 C30 C31 -3.6(2) . . . . ?
C28 C29 C30 N4 170.97(13) . . . . ?
C29 C30 C31 C32 3.3(2) . . . . ?
N4 C30 C31 C32 -171.22(13) . . . . ?
C30 C31 C32 C27 0.2(2) . . . . ?
C28 C27 C32 C31 -3.26(19) . . . . ?
C26 C27 C32 C31 171.66(12) . . . . ?
C31 C30 N4 C33 -76.2(2) . . . . ?
C29 C30 N4 C33 109.19(17) . . . . ?
C31 C30 N4 C44 95.41(17) . . . . ?
C29 C30 N4 C44 -79.15(19) . . . . ?
C44 N4 C33 C34 177.84(15) . . . . ?
C30 N4 C33 C34 -10.6(2) . . . . ?
C44 N4 C33 C38 -0.5(2) . . . . ?
C30 N4 C33 C38 171.10(14) . . . . ?
N4 C33 C34 C35 -177.76(15) . . . . ?
C38 C33 C34 C35 0.6(2) . . . . ?
C33 C34 C35 C36 -0.5(2) . . . . ?
C34 C35 C36 C37 0.1(2) . . . . ?
C35 C36 C37 C38 0.2(2) . . . . ?
C36 C37 C38 O2 179.14(14) . . . . ?
C36 C37 C38 C33 -0.2(2) . . . . ?
C34 C33 C38 C37 -0.2(2) . . . . ?
N4 C33 C38 C37 178.16(15) . . . . ?
C34 C33 C38 O2 -179.50(14) . . . . ?
N4 C33 C38 O2 -1.1(2) . . . . ?
C37 C38 O2 C39 -176.50(14) . . . . ?
C33 C38 O2 C39 2.8(2) . . . . ?
C38 O2 C39 C40 176.67(14) . . . . ?
C38 O2 C39 C44 -3.0(2) . . . . ?
O2 C39 C40 C41 -179.75(14) . . . . ?
C44 C39 C40 C41 -0.1(2) . . . . ?
C39 C40 C41 C42 -1.0(2) . . . . ?
C40 C41 C42 C43 0.9(2) . . . . ?
C41 C42 C43 C44 0.3(2) . . . . ?
C42 C43 C44 C39 -1.5(2) . . . . ?
C42 C43 C44 N4 178.02(15) . . . . ?
C40 C39 C44 C43 1.3(2) . . . . ?
O2 C39 C44 C43 -179.03(14) . . . . ?
C40 C39 C44 N4 -178.15(14) . . . . ?
O2 C39 C44 N4 1.5(2) . . . . ?
C33 N4 C44 C43 -179.16(15) . . . . ?
C30 N4 C44 C43 9.0(2) . . . . ?
C33 N4 C44 C39 0.3(2) . . . . ?
C30 N4 C44 C39 -171.52(14) . . . . ?

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
C40 H40 Cl1 0.93(2) 2.92(2) 3.6713(16) 138.8(18) 4_676 yes
C45 H45 N3 0.938(19) 2.581(19) 3.4004(19) 146.1(15) . yes

_refine_diff_density_max         0.933
_refine_diff_density_min         -0.671
_refine_diff_density_rms         0.062


#===END
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: deuterochlorform/methanol'
