# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_WDE0056_10B_A_0m
_audit_block_doi                 10.5517/ccdc.csd.cc2dcyqg
_database_code_depnum_ccdc_archive 'CCDC 2216026'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/D2CC06978D 2023
loop_
_audit_author_name
_audit_author_address
'Maja Morawiak'
;Institute of Organic Chemistry Polish Academy of Science
Poland
;
_audit_update_record             
;
2022-10-28 deposited with the CCDC.	2023-12-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C43 H34 N4, 2(Cl)'
_chemical_formula_sum            'C43 H34 Cl2 N4'
_chemical_formula_weight         677.64

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

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

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

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

_cell_length_a                   12.7869(3)
_cell_length_b                   14.6254(3)
_cell_length_c                   18.9250(4)
_cell_angle_alpha                90
_cell_angle_beta                 100.7860(10)
_cell_angle_gamma                90
_cell_volume                     3476.70(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4140
_cell_measurement_theta_min      3.85
_cell_measurement_theta_max      68.43

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.295
_exptl_crystal_F_000             1416
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.270
_exptl_crystal_size_mid          0.255
_exptl_crystal_size_min          0.168
_exptl_absorpt_coefficient_mu    1.963
_shelx_estimated_absorpt_T_min   0.619
_shelx_estimated_absorpt_T_max   0.734
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.6190
_exptl_absorpt_correction_T_max  0.7340
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            50145
_diffrn_reflns_av_unetI/netI     0.0434
_diffrn_reflns_av_R_equivalents  0.0813
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         3.845
_diffrn_reflns_theta_max         68.427
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             6382
_reflns_number_gt                4140
_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_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)+(0.1597P)²+2.2434P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0005(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         6382
_refine_ls_number_parameters     455
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1178
_refine_ls_R_factor_gt           0.0822
_refine_ls_wR_factor_ref         0.2810
_refine_ls_wR_factor_gt          0.2429
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.046
_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
Cl2 Cl 0.9212(3) 0.5356(3) 0.9456(3) 0.279(2) Uani 1 1 d . . . . .
N1 N 0.2659(3) 0.4873(2) 0.52827(15) 0.0591(8) Uani 1 1 d . . . . .
N2 N 0.1462(2) 0.7321(2) 0.29834(16) 0.0530(8) Uani 1 1 d . . . . .
N3 N -0.0478(2) 0.9317(2) 0.34069(15) 0.0505(7) Uani 1 1 d . . . . .
N4 N 0.1584(2) 1.0026(2) 0.35174(16) 0.0557(8) Uani 1 1 d . . . . .
C1 C 0.2303(3) 0.4964(2) 0.59353(18) 0.0479(8) Uani 1 1 d . . . . .
C2 C 0.1581(3) 0.5647(3) 0.6022(2) 0.0539(9) Uani 1 1 d . . . . .
H2 H 0.1330 0.6038 0.5640 0.065 Uiso 1 1 calc R U . . .
C3 C 0.1231(3) 0.5757(3) 0.6656(2) 0.0615(10) Uani 1 1 d . . . . .
H3 H 0.0762 0.6227 0.6708 0.074 Uiso 1 1 calc R U . . .
C4 C 0.1579(3) 0.5167(3) 0.7219(2) 0.0691(11) Uani 1 1 d . . . . .
H4 H 0.1331 0.5223 0.7648 0.083 Uiso 1 1 calc R U . . .
C5 C 0.2302(3) 0.4491(3) 0.7135(2) 0.0624(10) Uani 1 1 d . . . . .
H5 H 0.2540 0.4100 0.7519 0.075 Uiso 1 1 calc R U . . .
C6 C 0.2684(3) 0.4372(3) 0.65081(18) 0.0499(8) Uani 1 1 d . . . . .
C7 C 0.3583(3) 0.3706(3) 0.64715(19) 0.0589(10) Uani 1 1 d . . . . .
C8 C 0.3665(3) 0.3506(2) 0.56917(18) 0.0503(8) Uani 1 1 d . . . . .
C9 C 0.4227(4) 0.2772(3) 0.5513(3) 0.0838(14) Uani 1 1 d . . . . .
H9 H 0.4509 0.2360 0.5873 0.101 Uiso 1 1 calc R U . . .
C10 C 0.4397(6) 0.2616(4) 0.4822(3) 0.110(2) Uani 1 1 d . . . . .
H10 H 0.4778 0.2106 0.4721 0.132 Uiso 1 1 calc R U . . .
C11 C 0.4000(4) 0.3214(4) 0.4297(2) 0.0869(15) Uani 1 1 d . . . . .
H11 H 0.4119 0.3120 0.3833 0.104 Uiso 1 1 calc R U . . .
C12 C 0.3424(4) 0.3957(3) 0.4441(2) 0.0661(11) Uani 1 1 d . . . . .
H12 H 0.3153 0.4364 0.4074 0.079 Uiso 1 1 calc R U . . .
C13 C 0.3242(3) 0.4107(2) 0.51413(18) 0.0497(8) Uani 1 1 d . . . . .
C14 C 0.2331(3) 0.5523(3) 0.47170(18) 0.0543(9) Uani 1 1 d . . . . .
C15 C 0.1307(3) 0.5508(3) 0.43133(19) 0.0536(9) Uani 1 1 d . . . . .
H15 H 0.0815 0.5091 0.4428 0.064 Uiso 1 1 calc R U . . .
C16 C 0.1004(3) 0.6103(2) 0.37422(18) 0.0485(8) Uani 1 1 d . . . . .
H16 H 0.0311 0.6093 0.3482 0.058 Uiso 1 1 calc R U . . .
C17 C 0.1745(3) 0.6721(2) 0.35574(17) 0.0441(8) Uani 1 1 d . . . . .
C18 C 0.2766(3) 0.6746(3) 0.39818(19) 0.0534(9) Uani 1 1 d . . . . .
H18 H 0.3263 0.7165 0.3876 0.064 Uiso 1 1 calc R U . . .
C19 C 0.3042(3) 0.6159(3) 0.45521(19) 0.0585(10) Uani 1 1 d . . . . .
H19 H 0.3721 0.6191 0.4832 0.070 Uiso 1 1 calc R U . . .
C20 C 0.0423(3) 0.7362(2) 0.25536(17) 0.0460(8) Uani 1 1 d . . . . .
C21 C 0.0040(3) 0.6669(3) 0.2076(2) 0.0557(9) Uani 1 1 d . . . . .
H21 H 0.0453 0.6153 0.2044 0.067 Uiso 1 1 calc R U . . .
C22 C -0.0958(3) 0.6748(3) 0.1646(2) 0.0617(10) Uani 1 1 d . . . . .
H22 H -0.1221 0.6279 0.1331 0.074 Uiso 1 1 calc R U . . .
C23 C -0.1562(3) 0.7518(3) 0.1685(2) 0.0607(10) Uani 1 1 d . . . . .
C24 C -0.1182(3) 0.8211(3) 0.21560(19) 0.0550(9) Uani 1 1 d . . . . .
H24 H -0.1598 0.8727 0.2181 0.066 Uiso 1 1 calc R U . . .
C25 C -0.0180(3) 0.8147(2) 0.25953(17) 0.0449(8) Uani 1 1 d . . . . .
C26 C 0.0226(2) 0.8919(2) 0.30808(16) 0.0451(8) Uani 1 1 d . . . . .
C27 C 0.1291(3) 0.9266(2) 0.31509(17) 0.0476(8) Uani 1 1 d . . . . .
C28 C 0.2116(2) 0.8848(2) 0.27981(17) 0.0461(8) Uani 1 1 d . . . . .
C29 C 0.2848(3) 0.9399(3) 0.2537(2) 0.0557(9) Uani 1 1 d . . . . .
C30 C 0.3645(3) 0.9032(3) 0.2236(2) 0.0625(10) Uani 1 1 d . . . . .
H30 H 0.4135 0.9412 0.2077 0.075 Uiso 1 1 calc R U . . .
C31 C 0.3721(3) 0.8087(3) 0.2167(2) 0.0638(10) Uani 1 1 d . . . . .
H31 H 0.4253 0.7837 0.1952 0.077 Uiso 1 1 calc R U . . .
C32 C 0.3012(3) 0.7527(3) 0.2417(2) 0.0573(9) Uani 1 1 d . . . . .
H32 H 0.3065 0.6896 0.2372 0.069 Uiso 1 1 calc R U . . .
C33 C 0.2213(2) 0.7898(2) 0.27383(18) 0.0471(8) Uani 1 1 d . . . . .
C34 C -0.0166(3) 1.0075(3) 0.38098(18) 0.0510(8) Uani 1 1 d . . . . .
C35 C -0.0871(3) 1.0514(3) 0.41830(19) 0.0579(9) Uani 1 1 d . . . . .
H35 H -0.1552 1.0276 0.4155 0.069 Uiso 1 1 calc R U . . .
C36 C -0.0591(3) 1.1283(3) 0.45884(19) 0.0592(10) Uani 1 1 d . . . . .
C37 C 0.0445(4) 1.1651(3) 0.4633(2) 0.0672(11) Uani 1 1 d . . . . .
C38 C 0.1145(3) 1.1233(3) 0.4268(2) 0.0669(11) Uani 1 1 d . . . . .
H38 H 0.1821 1.1481 0.4293 0.080 Uiso 1 1 calc R U . . .
C39 C 0.0866(3) 1.0436(3) 0.38555(19) 0.0532(9) Uani 1 1 d . . . . .
C40 C 0.3425(6) 0.2805(4) 0.6867(3) 0.117(2) Uani 1 1 d . . . . .
H40A H 0.3362 0.2938 0.7354 0.175 Uiso 1 1 calc R U . . .
H40B H 0.4026 0.2411 0.6866 0.175 Uiso 1 1 calc R U . . .
H40C H 0.2790 0.2506 0.6625 0.175 Uiso 1 1 calc R U . . .
C41 C 0.4631(4) 0.4173(5) 0.6815(3) 0.101(2) Uani 1 1 d . . . . .
H41A H 0.4727 0.4717 0.6551 0.152 Uiso 1 1 calc R U . . .
H41B H 0.5214 0.3762 0.6805 0.152 Uiso 1 1 calc R U . . .
H41C H 0.4608 0.4330 0.7305 0.152 Uiso 1 1 calc R U . . .
C42 C -0.1358(4) 1.1716(3) 0.4995(2) 0.0736(12) Uani 1 1 d . . . . .
H42A H -0.1996 1.1356 0.4936 0.110 Uiso 1 1 calc R U . . .
H42B H -0.1529 1.2321 0.4813 0.110 Uiso 1 1 calc R U . . .
H42C H -0.1041 1.1749 0.5496 0.110 Uiso 1 1 calc R U . . .
C43 C 0.0786(5) 1.2491(4) 0.5075(3) 0.0981(17) Uani 1 1 d . . . . .
H43A H 0.0831 1.2352 0.5576 0.147 Uiso 1 1 calc R U . . .
H43B H 0.0273 1.2970 0.4939 0.147 Uiso 1 1 calc R U . . .
H43C H 0.1469 1.2689 0.4994 0.147 Uiso 1 1 calc R U . . .
H23 H -0.223(4) 0.755(3) 0.138(2) 0.065(11) Uiso 1 1 d . . . . .
H29 H 0.275(3) 1.003(3) 0.261(2) 0.061(11) Uiso 1 1 d . . . . .
Cl1 Cl 0.8788(7) 0.4627(5) 1.0507(6) 0.477(6) 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 C13 1.400(4) . ?
N1 C1 1.400(4) . ?
N1 C14 1.434(4) . ?
N2 C17 1.391(4) . ?
N2 C33 1.419(4) . ?
N2 C20 1.424(4) . ?
N3 C26 1.319(4) . ?
N3 C34 1.362(5) . ?
N4 C27 1.326(5) . ?
N4 C39 1.354(5) . ?
C1 C2 1.392(5) . ?
C1 C6 1.401(5) . ?
C2 C3 1.366(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.378(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.383(6) . ?
C4 H4 0.9300 . ?
C5 C6 1.377(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.518(5) . ?
C7 C8 1.527(5) . ?
C7 C41 1.536(6) . ?
C7 C40 1.548(6) . ?
C8 C9 1.370(6) . ?
C8 C13 1.392(5) . ?
C9 C10 1.384(7) . ?
C9 H9 0.9300 . ?
C10 C11 1.350(7) . ?
C10 H10 0.9300 . ?
C11 C12 1.368(6) . ?
C11 H11 0.9300 . ?
C12 C13 1.405(5) . ?
C12 H12 0.9300 . ?
C14 C19 1.376(5) . ?
C14 C15 1.387(5) . ?
C15 C16 1.385(5) . ?
C15 H15 0.9300 . ?
C16 C17 1.400(5) . ?
C16 H16 0.9300 . ?
C17 C18 1.400(5) . ?
C18 C19 1.373(5) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C20 C21 1.384(5) . ?
C20 C25 1.394(5) . ?
C21 C22 1.384(6) . ?
C21 H21 0.9300 . ?
C22 C23 1.375(6) . ?
C22 H22 0.9300 . ?
C23 C24 1.376(5) . ?
C23 H23 0.94(4) . ?
C24 C25 1.394(5) . ?
C24 H24 0.9300 . ?
C25 C26 1.487(5) . ?
C26 C27 1.436(5) . ?
C27 C28 1.482(5) . ?
C28 C29 1.394(5) . ?
C28 C33 1.401(5) . ?
C29 C30 1.366(5) . ?
C29 H29 0.94(4) . ?
C30 C31 1.393(6) . ?
C30 H30 0.9300 . ?
C31 C32 1.369(5) . ?
C31 H31 0.9300 . ?
C32 C33 1.394(5) . ?
C32 H32 0.9300 . ?
C34 C35 1.401(5) . ?
C34 C39 1.408(5) . ?
C35 C36 1.371(6) . ?
C35 H35 0.9300 . ?
C36 C37 1.417(6) . ?
C36 C42 1.496(5) . ?
C37 C38 1.373(6) . ?
C37 C43 1.504(6) . ?
C38 C39 1.411(6) . ?
C38 H38 0.9300 . ?
C40 H40A 0.9600 . ?
C40 H40B 0.9600 . ?
C40 H40C 0.9600 . ?
C41 H41A 0.9600 . ?
C41 H41B 0.9600 . ?
C41 H41C 0.9600 . ?
C42 H42A 0.9600 . ?
C42 H42B 0.9600 . ?
C42 H42C 0.9600 . ?
C43 H43A 0.9600 . ?
C43 H43B 0.9600 . ?
C43 H43C 0.9600 . ?

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
C13 N1 C1 121.1(3) . . ?
C13 N1 C14 118.7(3) . . ?
C1 N1 C14 119.8(3) . . ?
C17 N2 C33 122.5(3) . . ?
C17 N2 C20 123.4(3) . . ?
C33 N2 C20 113.9(3) . . ?
C26 N3 C34 117.9(3) . . ?
C27 N4 C39 117.9(3) . . ?
C2 C1 N1 120.3(3) . . ?
C2 C1 C6 119.7(3) . . ?
N1 C1 C6 120.1(3) . . ?
C3 C2 C1 121.4(4) . . ?
C3 C2 H2 119.3 . . ?
C1 C2 H2 119.3 . . ?
C2 C3 C4 119.7(4) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 H3 120.2 . . ?
C3 C4 C5 119.0(4) . . ?
C3 C4 H4 120.5 . . ?
C5 C4 H4 120.5 . . ?
C6 C5 C4 122.7(4) . . ?
C6 C5 H5 118.6 . . ?
C4 C5 H5 118.6 . . ?
C5 C6 C1 117.5(3) . . ?
C5 C6 C7 120.9(3) . . ?
C1 C6 C7 121.2(3) . . ?
C6 C7 C8 110.9(3) . . ?
C6 C7 C41 107.7(3) . . ?
C8 C7 C41 106.4(3) . . ?
C6 C7 C40 110.9(4) . . ?
C8 C7 C40 110.0(4) . . ?
C41 C7 C40 110.8(4) . . ?
C9 C8 C13 117.3(3) . . ?
C9 C8 C7 121.5(3) . . ?
C13 C8 C7 121.0(3) . . ?
C8 C9 C10 123.0(4) . . ?
C8 C9 H9 118.5 . . ?
C10 C9 H9 118.5 . . ?
C11 C10 C9 119.0(5) . . ?
C11 C10 H10 120.5 . . ?
C9 C10 H10 120.5 . . ?
C10 C11 C12 120.7(4) . . ?
C10 C11 H11 119.6 . . ?
C12 C11 H11 119.6 . . ?
C11 C12 C13 120.1(4) . . ?
C11 C12 H12 120.0 . . ?
C13 C12 H12 120.0 . . ?
C8 C13 N1 120.5(3) . . ?
C8 C13 C12 119.9(3) . . ?
N1 C13 C12 119.5(3) . . ?
C19 C14 C15 118.8(3) . . ?
C19 C14 N1 120.2(3) . . ?
C15 C14 N1 121.0(4) . . ?
C16 C15 C14 121.1(3) . . ?
C16 C15 H15 119.4 . . ?
C14 C15 H15 119.4 . . ?
C15 C16 C17 119.8(3) . . ?
C15 C16 H16 120.1 . . ?
C17 C16 H16 120.1 . . ?
N2 C17 C16 120.9(3) . . ?
N2 C17 C18 120.6(3) . . ?
C16 C17 C18 118.4(3) . . ?
C19 C18 C17 120.6(3) . . ?
C19 C18 H18 119.7 . . ?
C17 C18 H18 119.7 . . ?
C18 C19 C14 121.2(3) . . ?
C18 C19 H19 119.4 . . ?
C14 C19 H19 119.4 . . ?
C21 C20 C25 120.5(3) . . ?
C21 C20 N2 121.4(3) . . ?
C25 C20 N2 118.0(3) . . ?
C22 C21 C20 119.8(4) . . ?
C22 C21 H21 120.1 . . ?
C20 C21 H21 120.1 . . ?
C23 C22 C21 120.2(4) . . ?
C23 C22 H22 119.9 . . ?
C21 C22 H22 119.9 . . ?
C22 C23 C24 120.2(4) . . ?
C22 C23 H23 118(2) . . ?
C24 C23 H23 122(3) . . ?
C23 C24 C25 120.7(3) . . ?
C23 C24 H24 119.6 . . ?
C25 C24 H24 119.6 . . ?
C24 C25 C20 118.5(3) . . ?
C24 C25 C26 119.6(3) . . ?
C20 C25 C26 121.8(3) . . ?
N3 C26 C27 121.2(3) . . ?
N3 C26 C25 115.7(3) . . ?
C27 C26 C25 122.8(3) . . ?
N4 C27 C26 121.0(3) . . ?
N4 C27 C28 115.3(3) . . ?
C26 C27 C28 123.7(3) . . ?
C29 C28 C33 118.0(3) . . ?
C29 C28 C27 120.2(3) . . ?
C33 C28 C27 121.8(3) . . ?
C30 C29 C28 121.5(4) . . ?
C30 C29 H29 125(3) . . ?
C28 C29 H29 113(2) . . ?
C29 C30 C31 120.0(4) . . ?
C29 C30 H30 120.0 . . ?
C31 C30 H30 120.0 . . ?
C32 C31 C30 119.9(4) . . ?
C32 C31 H31 120.0 . . ?
C30 C31 H31 120.0 . . ?
C31 C32 C33 120.3(4) . . ?
C31 C32 H32 119.8 . . ?
C33 C32 H32 119.8 . . ?
C32 C33 C28 120.3(3) . . ?
C32 C33 N2 120.5(3) . . ?
C28 C33 N2 119.2(3) . . ?
N3 C34 C35 120.4(3) . . ?
N3 C34 C39 120.8(3) . . ?
C35 C34 C39 118.7(3) . . ?
C36 C35 C34 122.2(4) . . ?
C36 C35 H35 118.9 . . ?
C34 C35 H35 118.9 . . ?
C35 C36 C37 119.3(4) . . ?
C35 C36 C42 120.4(4) . . ?
C37 C36 C42 120.3(4) . . ?
C38 C37 C36 119.4(4) . . ?
C38 C37 C43 119.7(4) . . ?
C36 C37 C43 120.9(4) . . ?
C37 C38 C39 121.6(4) . . ?
C37 C38 H38 119.2 . . ?
C39 C38 H38 119.2 . . ?
N4 C39 C34 121.0(3) . . ?
N4 C39 C38 120.2(3) . . ?
C34 C39 C38 118.8(4) . . ?
C7 C40 H40A 109.5 . . ?
C7 C40 H40B 109.5 . . ?
H40A C40 H40B 109.5 . . ?
C7 C40 H40C 109.5 . . ?
H40A C40 H40C 109.5 . . ?
H40B C40 H40C 109.5 . . ?
C7 C41 H41A 109.5 . . ?
C7 C41 H41B 109.5 . . ?
H41A C41 H41B 109.5 . . ?
C7 C41 H41C 109.5 . . ?
H41A C41 H41C 109.5 . . ?
H41B C41 H41C 109.5 . . ?
C36 C42 H42A 109.5 . . ?
C36 C42 H42B 109.5 . . ?
H42A C42 H42B 109.5 . . ?
C36 C42 H42C 109.5 . . ?
H42A C42 H42C 109.5 . . ?
H42B C42 H42C 109.5 . . ?
C37 C43 H43A 109.5 . . ?
C37 C43 H43B 109.5 . . ?
H43A C43 H43B 109.5 . . ?
C37 C43 H43C 109.5 . . ?
H43A C43 H43C 109.5 . . ?
H43B C43 H43C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C13 N1 C1 C2 -169.3(3) . . . . ?
C14 N1 C1 C2 4.0(5) . . . . ?
C13 N1 C1 C6 11.5(5) . . . . ?
C14 N1 C1 C6 -175.2(3) . . . . ?
N1 C1 C2 C3 -179.2(4) . . . . ?
C6 C1 C2 C3 0.0(5) . . . . ?
C1 C2 C3 C4 -1.6(6) . . . . ?
C2 C3 C4 C5 1.9(6) . . . . ?
C3 C4 C5 C6 -0.8(7) . . . . ?
C4 C5 C6 C1 -0.7(6) . . . . ?
C4 C5 C6 C7 171.8(4) . . . . ?
C2 C1 C6 C5 1.1(5) . . . . ?
N1 C1 C6 C5 -179.7(4) . . . . ?
C2 C1 C6 C7 -171.4(3) . . . . ?
N1 C1 C6 C7 7.8(5) . . . . ?
C5 C6 C7 C8 164.9(4) . . . . ?
C1 C6 C7 C8 -22.8(5) . . . . ?
C5 C6 C7 C41 -79.0(5) . . . . ?
C1 C6 C7 C41 93.2(4) . . . . ?
C5 C6 C7 C40 42.4(5) . . . . ?
C1 C6 C7 C40 -145.3(4) . . . . ?
C6 C7 C8 C9 -163.9(4) . . . . ?
C41 C7 C8 C9 79.3(5) . . . . ?
C40 C7 C8 C9 -40.9(6) . . . . ?
C6 C7 C8 C13 21.4(5) . . . . ?
C41 C7 C8 C13 -95.4(4) . . . . ?
C40 C7 C8 C13 144.5(4) . . . . ?
C13 C8 C9 C10 0.8(8) . . . . ?
C7 C8 C9 C10 -174.1(5) . . . . ?
C8 C9 C10 C11 0.5(10) . . . . ?
C9 C10 C11 C12 -1.0(10) . . . . ?
C10 C11 C12 C13 0.2(8) . . . . ?
C9 C8 C13 N1 -179.9(4) . . . . ?
C7 C8 C13 N1 -5.0(5) . . . . ?
C9 C8 C13 C12 -1.6(6) . . . . ?
C7 C8 C13 C12 173.3(4) . . . . ?
C1 N1 C13 C8 -12.9(5) . . . . ?
C14 N1 C13 C8 173.8(4) . . . . ?
C1 N1 C13 C12 168.8(4) . . . . ?
C14 N1 C13 C12 -4.6(5) . . . . ?
C11 C12 C13 C8 1.2(6) . . . . ?
C11 C12 C13 N1 179.5(4) . . . . ?
C13 N1 C14 C19 -79.2(5) . . . . ?
C1 N1 C14 C19 107.4(4) . . . . ?
C13 N1 C14 C15 98.9(4) . . . . ?
C1 N1 C14 C15 -74.5(5) . . . . ?
C19 C14 C15 C16 1.6(6) . . . . ?
N1 C14 C15 C16 -176.6(3) . . . . ?
C14 C15 C16 C17 1.2(5) . . . . ?
C33 N2 C17 C16 -174.1(3) . . . . ?
C20 N2 C17 C16 0.6(5) . . . . ?
C33 N2 C17 C18 8.5(5) . . . . ?
C20 N2 C17 C18 -176.8(3) . . . . ?
C15 C16 C17 N2 179.6(3) . . . . ?
C15 C16 C17 C18 -2.9(5) . . . . ?
N2 C17 C18 C19 179.4(3) . . . . ?
C16 C17 C18 C19 2.0(5) . . . . ?
C17 C18 C19 C14 0.8(6) . . . . ?
C15 C14 C19 C18 -2.6(6) . . . . ?
N1 C14 C19 C18 175.5(3) . . . . ?
C17 N2 C20 C21 -71.2(4) . . . . ?
C33 N2 C20 C21 104.0(4) . . . . ?
C17 N2 C20 C25 112.6(4) . . . . ?
C33 N2 C20 C25 -72.3(4) . . . . ?
C25 C20 C21 C22 -1.3(5) . . . . ?
N2 C20 C21 C22 -177.5(3) . . . . ?
C20 C21 C22 C23 1.0(6) . . . . ?
C21 C22 C23 C24 -0.6(6) . . . . ?
C22 C23 C24 C25 0.5(6) . . . . ?
C23 C24 C25 C20 -0.8(5) . . . . ?
C23 C24 C25 C26 177.9(3) . . . . ?
C21 C20 C25 C24 1.2(5) . . . . ?
N2 C20 C25 C24 177.5(3) . . . . ?
C21 C20 C25 C26 -177.5(3) . . . . ?
N2 C20 C25 C26 -1.2(4) . . . . ?
C34 N3 C26 C27 0.4(5) . . . . ?
C34 N3 C26 C25 -174.6(3) . . . . ?
C24 C25 C26 N3 40.3(4) . . . . ?
C20 C25 C26 N3 -141.1(3) . . . . ?
C24 C25 C26 C27 -134.6(3) . . . . ?
C20 C25 C26 C27 44.0(5) . . . . ?
C39 N4 C27 C26 3.5(5) . . . . ?
C39 N4 C27 C28 -179.6(3) . . . . ?
N3 C26 C27 N4 -3.3(5) . . . . ?
C25 C26 C27 N4 171.4(3) . . . . ?
N3 C26 C27 C28 180.0(3) . . . . ?
C25 C26 C27 C28 -5.3(5) . . . . ?
N4 C27 C28 C29 -33.0(5) . . . . ?
C26 C27 C28 C29 143.9(3) . . . . ?
N4 C27 C28 C33 144.7(3) . . . . ?
C26 C27 C28 C33 -38.4(5) . . . . ?
C33 C28 C29 C30 -0.6(5) . . . . ?
C27 C28 C29 C30 177.3(3) . . . . ?
C28 C29 C30 C31 1.7(6) . . . . ?
C29 C30 C31 C32 -1.5(6) . . . . ?
C30 C31 C32 C33 0.1(6) . . . . ?
C31 C32 C33 C28 1.1(5) . . . . ?
C31 C32 C33 N2 178.6(3) . . . . ?
C29 C28 C33 C32 -0.8(5) . . . . ?
C27 C28 C33 C32 -178.6(3) . . . . ?
C29 C28 C33 N2 -178.4(3) . . . . ?
C27 C28 C33 N2 3.8(5) . . . . ?
C17 N2 C33 C32 67.1(5) . . . . ?
C20 N2 C33 C32 -108.0(4) . . . . ?
C17 N2 C33 C28 -115.3(4) . . . . ?
C20 N2 C33 C28 69.5(4) . . . . ?
C26 N3 C34 C35 -178.4(3) . . . . ?
C26 N3 C34 C39 2.1(5) . . . . ?
N3 C34 C35 C36 -179.4(3) . . . . ?
C39 C34 C35 C36 0.2(6) . . . . ?
C34 C35 C36 C37 0.1(6) . . . . ?
C34 C35 C36 C42 -178.3(3) . . . . ?
C35 C36 C37 C38 0.2(6) . . . . ?
C42 C36 C37 C38 178.7(4) . . . . ?
C35 C36 C37 C43 -179.7(4) . . . . ?
C42 C36 C37 C43 -1.2(6) . . . . ?
C36 C37 C38 C39 -0.9(7) . . . . ?
C43 C37 C38 C39 179.0(4) . . . . ?
C27 N4 C39 C34 -1.0(5) . . . . ?
C27 N4 C39 C38 178.4(3) . . . . ?
N3 C34 C39 N4 -1.9(5) . . . . ?
C35 C34 C39 N4 178.6(3) . . . . ?
N3 C34 C39 C38 178.7(3) . . . . ?
C35 C34 C39 C38 -0.8(5) . . . . ?
C37 C38 C39 N4 -178.2(4) . . . . ?
C37 C38 C39 C34 1.2(6) . . . . ?

_refine_diff_density_max         0.801
_refine_diff_density_min         -0.844
_refine_diff_density_rms         0.065

_shelxl_version_number           2014-3



####################################################################### 
# 
# 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_KBA_0226_10B_0m
_database_code_depnum_ccdc_archive 'CCDC 2290709'
loop_
_audit_author_name
_audit_author_address
'Maja Morawiak'
;Institute of Organic Chemistry Polish Academy of Science
Poland
;
_audit_update_record             
;
2023-08-25 deposited with the CCDC.	2023-12-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C32 H26 N2 O2, C H2 Cl1.71, 0.29(Cl)'
_chemical_formula_sum            'C33 H28 Cl2 N2 O2'
_chemical_formula_weight         555.47

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

_space_group_crystal_system      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                   9.672(2)
_cell_length_b                   12.189(3)
_cell_length_c                   13.165(3)
_cell_angle_alpha                87.549(15)
_cell_angle_beta                 80.714(15)
_cell_angle_gamma                67.560(14)
_cell_volume                     1415.3(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2110
_cell_measurement_theta_min      3.40
_cell_measurement_theta_max      68.77

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.303
_exptl_crystal_F_000             580
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.540
_exptl_crystal_size_mid          0.259
_exptl_crystal_size_min          0.147
_exptl_absorpt_coefficient_mu    2.320
_shelx_estimated_absorpt_T_min   0.367
_shelx_estimated_absorpt_T_max   0.727
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.3670
_exptl_absorpt_correction_T_max  0.7270
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
 Crystal selected for X-ray experiment was thin plate
 with dimensions 0.540 mm x 0.259 mm x 0.147 mm.
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            31074
_diffrn_reflns_av_unetI/netI     0.0962
_diffrn_reflns_av_R_equivalents  0.0787
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.402
_diffrn_reflns_theta_max         68.767
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.934
_diffrn_measured_fraction_theta_full 0.945
_diffrn_reflns_Laue_measured_fraction_max 0.934
_diffrn_reflns_Laue_measured_fraction_full 0.945
_diffrn_reflns_point_group_measured_fraction_max 0.934
_diffrn_reflns_point_group_measured_fraction_full 0.945
_reflns_number_total             4893
_reflns_number_gt                2110
_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_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)+(0.0658P)²+2.9893P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_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         4893
_refine_ls_number_parameters     372
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1981
_refine_ls_R_factor_gt           0.0975
_refine_ls_wR_factor_ref         0.2405
_refine_ls_wR_factor_gt          0.1956
_refine_ls_goodness_of_fit_ref   0.971
_refine_ls_restrained_S_all      0.971
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.001

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 1.0666(4) 0.6445(3) 0.0984(3) 0.0709(11) Uani 1 1 d . . . . .
O2 O 1.2247(4) 0.8623(4) 0.2904(3) 0.0820(13) Uani 1 1 d . . . . .
N1 N 0.4976(5) 1.0952(4) 0.4033(3) 0.0555(12) Uani 1 1 d . . . . .
N2 N 1.1401(4) 0.7599(3) 0.1908(3) 0.0473(10) Uani 1 1 d . . . . .
C1 C 0.3790(7) 1.1848(5) 0.4596(4) 0.0575(15) Uani 1 1 d . . . . .
C2 C 0.3790(7) 1.2657(5) 0.5290(4) 0.0702(17) Uani 1 1 d . . . . .
H2 H 0.4685 1.2660 0.5461 0.084 Uiso 1 1 calc R U . . .
C3 C 0.2374(9) 1.3477(6) 0.5726(5) 0.085(2) Uani 1 1 d . . . . .
H3 H 0.2323 1.4043 0.6197 0.102 Uiso 1 1 calc R U . . .
C4 C 0.1052(9) 1.3465(6) 0.5473(6) 0.086(2) Uani 1 1 d . . . . .
H4 H 0.0130 1.4028 0.5773 0.103 Uiso 1 1 calc R U . . .
C5 C 0.1064(7) 1.2643(6) 0.4790(5) 0.0784(19) Uani 1 1 d . . . . .
H5 H 0.0160 1.2642 0.4635 0.094 Uiso 1 1 calc R U . . .
C6 C 0.2451(7) 1.1807(5) 0.4329(4) 0.0603(15) Uani 1 1 d . . . . .
C7 C 0.2874(6) 1.0851(5) 0.3604(4) 0.0632(16) Uani 1 1 d . . . . .
H7 H 0.2216 1.0621 0.3304 0.076 Uiso 1 1 calc R U . . .
C8 C 0.4410(6) 1.0338(5) 0.3432(4) 0.0558(14) Uani 1 1 d . . . . .
C9 C 0.5713(6) 0.9416(5) 0.2845(4) 0.0490(13) Uani 1 1 d . . . . .
C10 C 0.5985(6) 0.8506(5) 0.2163(4) 0.0557(14) Uani 1 1 d . . . . .
H10 H 0.5187 0.8356 0.1973 0.067 Uiso 1 1 calc R U . . .
C11 C 0.7481(6) 0.7812(5) 0.1762(4) 0.0534(14) Uani 1 1 d . . . . .
H11 H 0.7659 0.7200 0.1298 0.064 Uiso 1 1 calc R U . . .
C12 C 0.8719(6) 0.7989(4) 0.2021(4) 0.0463(13) Uani 1 1 d . . . . .
C13 C 0.8447(6) 0.8908(4) 0.2729(4) 0.0449(12) Uani 1 1 d . . . . .
C14 C 0.9595(6) 0.9175(4) 0.3073(4) 0.0483(13) Uani 1 1 d . . . . .
C15 C 0.9174(6) 1.0090(5) 0.3785(4) 0.0595(15) Uani 1 1 d . . . . .
H15 H 0.9932 1.0265 0.4007 0.071 Uiso 1 1 calc R U . . .
C16 C 0.7655(6) 1.0773(5) 0.4192(4) 0.0600(15) Uani 1 1 d . . . . .
H16 H 0.7406 1.1380 0.4676 0.072 Uiso 1 1 calc R U . . .
C17 C 0.6564(6) 1.0502(4) 0.3842(4) 0.0473(13) Uani 1 1 d . . . . .
C18 C 0.6974(6) 0.9577(4) 0.3116(4) 0.0455(12) Uani 1 1 d . . . . .
C19 C 1.0283(6) 0.7269(5) 0.1587(4) 0.0483(13) Uani 1 1 d . . . . .
C20 C 1.1167(6) 0.8477(5) 0.2648(4) 0.0549(14) Uani 1 1 d . . . . .
C21 C 1.2962(5) 0.6978(4) 0.1440(4) 0.0477(13) Uani 1 1 d . . . . .
C22 C 1.3517(6) 0.7430(5) 0.0552(4) 0.0563(14) Uani 1 1 d . . . . .
C23 C 1.5017(7) 0.6809(6) 0.0128(4) 0.0672(17) Uani 1 1 d . . . . .
H23 H 1.5423 0.7084 -0.0471 0.081 Uiso 1 1 calc R U . . .
C24 C 1.5912(7) 0.5811(6) 0.0561(5) 0.0685(17) Uani 1 1 d . . . . .
H24 H 1.6913 0.5411 0.0260 0.082 Uiso 1 1 calc R U . . .
C25 C 1.5330(7) 0.5400(5) 0.1439(5) 0.0645(16) Uani 1 1 d . . . . .
H25 H 1.5951 0.4719 0.1731 0.077 Uiso 1 1 calc R U . . .
C26 C 1.3843(6) 0.5965(5) 0.1909(4) 0.0533(14) Uani 1 1 d . . . . .
C27 C 1.2531(8) 0.8539(6) 0.0064(5) 0.0806(19) Uani 1 1 d . . . . .
H27 H 1.1526 0.8828 0.0487 0.097 Uiso 1 1 calc R U . . .
C28 C 1.2346(11) 0.8300(7) -0.0997(7) 0.156(4) Uani 1 1 d . . . . .
H28A H 1.3286 0.8137 -0.1452 0.234 Uiso 1 1 calc R U . . .
H28B H 1.1572 0.8982 -0.1229 0.234 Uiso 1 1 calc R U . . .
H28C H 1.2061 0.7626 -0.0992 0.234 Uiso 1 1 calc R U . . .
C29 C 1.3136(13) 0.9501(7) 0.0033(8) 0.180(5) Uani 1 1 d . . . . .
H29A H 1.4147 0.9222 -0.0344 0.270 Uiso 1 1 calc R U . . .
H29B H 1.3150 0.9718 0.0723 0.270 Uiso 1 1 calc R U . . .
H29C H 1.2501 1.0180 -0.0299 0.270 Uiso 1 1 calc R U . . .
C30 C 1.3244(7) 0.5486(5) 0.2882(4) 0.0662(16) Uani 1 1 d . . . . .
H30 H 1.2172 0.5997 0.3069 0.079 Uiso 1 1 calc R U . A 1
C31 C 1.3318(10) 0.4255(7) 0.2753(5) 0.119(3) Uani 1 1 d . . . . .
H31A H 1.2818 0.4224 0.2187 0.179 Uiso 1 1 calc R U . . .
H31B H 1.2825 0.4030 0.3372 0.179 Uiso 1 1 calc R U . . .
H31C H 1.4358 0.3718 0.2616 0.179 Uiso 1 1 calc R U . . .
C32A C 1.404(4) 0.554(2) 0.3789(8) 0.143(6) Uani 0.90(5) 1 d . . P B 1
H32A H 1.3558 0.5313 0.4408 0.214 Uiso 0.90(5) 1 calc R U P B 1
H32B H 1.3982 0.6341 0.3873 0.214 Uiso 0.90(5) 1 calc R U P B 1
H32C H 1.5087 0.5016 0.3650 0.214 Uiso 0.90(5) 1 calc R U P B 1
C32B C 1.332(8) 0.586(6) 0.370(6) 0.04(3) Uiso 0.10(5) 1 d . . P B 2
H32D H 1.4188 0.6076 0.3621 0.054 Uiso 0.10(5) 1 calc R U P B 2
H32E H 1.3418 0.5256 0.4203 0.054 Uiso 0.10(5) 1 calc R U P B 2
H32F H 1.2420 0.6544 0.3910 0.054 Uiso 0.10(5) 1 calc R U P B 2
C41 C 1.0132(10) 0.3786(8) 0.1323(7) 0.142(3) Uani 1 1 d . . . . .
H41A H 1.0538 0.4401 0.1184 0.171 Uiso 1 1 calc R U . C 1
H41B H 0.9489 0.3840 0.0814 0.171 Uiso 1 1 calc R U . C 1
Cl1A Cl 0.9126(11) 0.4029(17) 0.2433(9) 0.209(7) Uani 0.71(3) 1 d . . P D 1
Cl1B Cl 0.8795(17) 0.330(3) 0.2716(11) 0.176(7) Uani 0.29(3) 1 d . . P D 2
Cl2 Cl 1.1585(3) 0.2447(3) 0.1188(2) 0.1776(12) 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
O1 C19 1.210(5) . ?
O2 C20 1.224(5) . ?
N1 C1 1.377(6) . ?
N1 C17 1.403(6) . ?
N1 C8 1.410(6) . ?
N2 C20 1.407(6) . ?
N2 C19 1.416(6) . ?
N2 C21 1.448(6) . ?
C1 C2 1.374(7) . ?
C1 C6 1.414(7) . ?
C2 C3 1.398(8) . ?
C2 H2 0.9300 . ?
C3 C4 1.377(9) . ?
C3 H3 0.9300 . ?
C4 C5 1.371(8) . ?
C4 H4 0.9300 . ?
C5 C6 1.398(8) . ?
C5 H5 0.9300 . ?
C6 C7 1.429(7) . ?
C7 C8 1.358(7) . ?
C7 H7 0.9300 . ?
C8 C9 1.458(7) . ?
C9 C10 1.375(6) . ?
C9 C18 1.408(6) . ?
C10 C11 1.395(7) . ?
C10 H10 0.9300 . ?
C11 C12 1.391(6) . ?
C11 H11 0.9300 . ?
C12 C13 1.406(6) . ?
C12 C19 1.461(7) . ?
C13 C18 1.367(6) . ?
C13 C14 1.413(6) . ?
C14 C15 1.380(6) . ?
C14 C20 1.459(7) . ?
C15 C16 1.410(7) . ?
C15 H15 0.9300 . ?
C16 C17 1.367(7) . ?
C16 H16 0.9300 . ?
C17 C18 1.403(6) . ?
C21 C26 1.391(7) . ?
C21 C22 1.388(7) . ?
C22 C23 1.388(7) . ?
C22 C27 1.513(8) . ?
C23 C24 1.360(8) . ?
C23 H23 0.9300 . ?
C24 C25 1.364(7) . ?
C24 H24 0.9300 . ?
C25 C26 1.385(7) . ?
C25 H25 0.9300 . ?
C26 C30 1.507(7) . ?
C27 C29 1.494(10) . ?
C27 C28 1.491(9) . ?
C27 H27 0.9800 . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?
C29 H29A 0.9600 . ?
C29 H29B 0.9600 . ?
C29 H29C 0.9600 . ?
C30 C31 1.490(8) . ?
C30 C32B 1.21(8) . ?
C30 C32A 1.541(17) . ?
C30 H30 0.9800 . ?
C31 H31A 0.9600 . ?
C31 H31B 0.9600 . ?
C31 H31C 0.9600 . ?
C32A H32A 0.9600 . ?
C32A H32B 0.9600 . ?
C32A H32C 0.9600 . ?
C32B H32D 0.9600 . ?
C32B H32E 0.9600 . ?
C32B H32F 0.9600 . ?
C41 Cl1A 1.589(17) . ?
C41 Cl2 1.692(8) . ?
C41 Cl1B 2.26(2) . ?
C41 H41A 0.9700 . ?
C41 H41B 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C17 139.4(5) . . ?
C1 N1 C8 109.7(5) . . ?
C17 N1 C8 110.8(4) . . ?
C20 N2 C19 126.9(4) . . ?
C20 N2 C21 115.2(4) . . ?
C19 N2 C21 117.9(4) . . ?
N1 C1 C2 130.5(6) . . ?
N1 C1 C6 106.3(5) . . ?
C2 C1 C6 123.3(6) . . ?
C1 C2 C3 116.4(6) . . ?
C1 C2 H2 121.8 . . ?
C3 C2 H2 121.8 . . ?
C4 C3 C2 121.6(7) . . ?
C4 C3 H3 119.2 . . ?
C2 C3 H3 119.2 . . ?
C5 C4 C3 121.5(7) . . ?
C5 C4 H4 119.2 . . ?
C3 C4 H4 119.2 . . ?
C4 C5 C6 119.2(7) . . ?
C4 C5 H5 120.4 . . ?
C6 C5 H5 120.4 . . ?
C5 C6 C1 118.0(6) . . ?
C5 C6 C7 133.9(6) . . ?
C1 C6 C7 108.1(5) . . ?
C8 C7 C6 107.6(5) . . ?
C8 C7 H7 126.2 . . ?
C6 C7 H7 126.2 . . ?
C7 C8 N1 108.3(5) . . ?
C7 C8 C9 144.5(5) . . ?
N1 C8 C9 107.2(5) . . ?
C10 C9 C18 117.7(5) . . ?
C10 C9 C8 138.0(5) . . ?
C18 C9 C8 104.3(4) . . ?
C9 C10 C11 118.7(5) . . ?
C9 C10 H10 120.6 . . ?
C11 C10 H10 120.6 . . ?
C12 C11 C10 123.2(5) . . ?
C12 C11 H11 118.4 . . ?
C10 C11 H11 118.4 . . ?
C11 C12 C13 118.2(5) . . ?
C11 C12 C19 122.9(5) . . ?
C13 C12 C19 118.8(4) . . ?
C18 C13 C12 117.7(4) . . ?
C18 C13 C14 118.0(5) . . ?
C12 C13 C14 124.3(5) . . ?
C15 C14 C13 118.5(5) . . ?
C15 C14 C20 123.4(5) . . ?
C13 C14 C20 118.1(5) . . ?
C14 C15 C16 123.6(5) . . ?
C14 C15 H15 118.2 . . ?
C16 C15 H15 118.2 . . ?
C17 C16 C15 116.8(5) . . ?
C17 C16 H16 121.6 . . ?
C15 C16 H16 121.6 . . ?
C16 C17 N1 134.9(5) . . ?
C16 C17 C18 120.3(5) . . ?
N1 C17 C18 104.9(4) . . ?
C13 C18 C9 124.4(5) . . ?
C13 C18 C17 122.9(5) . . ?
C9 C18 C17 112.8(5) . . ?
O1 C19 N2 119.4(5) . . ?
O1 C19 C12 125.2(5) . . ?
N2 C19 C12 115.4(5) . . ?
O2 C20 N2 120.3(5) . . ?
O2 C20 C14 123.4(5) . . ?
N2 C20 C14 116.3(4) . . ?
C26 C21 C22 122.9(5) . . ?
C26 C21 N2 118.5(5) . . ?
C22 C21 N2 118.6(5) . . ?
C23 C22 C21 116.8(5) . . ?
C23 C22 C27 121.6(5) . . ?
C21 C22 C27 121.6(5) . . ?
C24 C23 C22 122.0(5) . . ?
C24 C23 H23 119.0 . . ?
C22 C23 H23 119.0 . . ?
C23 C24 C25 119.6(6) . . ?
C23 C24 H24 120.2 . . ?
C25 C24 H24 120.2 . . ?
C24 C25 C26 122.1(5) . . ?
C24 C25 H25 119.0 . . ?
C26 C25 H25 119.0 . . ?
C21 C26 C25 116.6(5) . . ?
C21 C26 C30 122.8(5) . . ?
C25 C26 C30 120.5(5) . . ?
C29 C27 C28 109.3(7) . . ?
C29 C27 C22 111.8(6) . . ?
C28 C27 C22 112.1(6) . . ?
C29 C27 H27 107.8 . . ?
C28 C27 H27 107.8 . . ?
C22 C27 H27 107.8 . . ?
C27 C28 H28A 109.5 . . ?
C27 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C27 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C27 C29 H29A 109.5 . . ?
C27 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C27 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C31 C30 C32B 122(3) . . ?
C31 C30 C26 113.2(5) . . ?
C32B C30 C26 118(3) . . ?
C31 C30 C32A 109.9(9) . . ?
C26 C30 C32A 112.1(7) . . ?
C31 C30 H30 107.1 . . ?
C26 C30 H30 107.1 . . ?
C32A C30 H30 107.1 . . ?
C30 C31 H31A 109.5 . . ?
C30 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
C30 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C30 C32A H32A 109.5 . . ?
C30 C32A H32B 109.5 . . ?
H32A C32A H32B 109.5 . . ?
C30 C32A H32C 109.5 . . ?
H32A C32A H32C 109.5 . . ?
H32B C32A H32C 109.5 . . ?
C30 C32B H32D 109.5 . . ?
C30 C32B H32E 109.4 . . ?
H32D C32B H32E 109.5 . . ?
C30 C32B H32F 109.5 . . ?
H32D C32B H32F 109.5 . . ?
H32E C32B H32F 109.5 . . ?
Cl1A C41 Cl2 113.9(8) . . ?
Cl2 C41 Cl1B 95.4(8) . . ?
Cl1A C41 H41A 108.8 . . ?
Cl2 C41 H41A 108.8 . . ?
Cl1A C41 H41B 108.8 . . ?
Cl2 C41 H41B 108.8 . . ?
H41A C41 H41B 107.7 . . ?

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
C17 N1 C1 C2 -4.9(10) . . . . ?
C8 N1 C1 C2 179.1(5) . . . . ?
C17 N1 C1 C6 175.1(6) . . . . ?
C8 N1 C1 C6 -0.9(5) . . . . ?
N1 C1 C2 C3 179.1(5) . . . . ?
C6 C1 C2 C3 -1.0(8) . . . . ?
C1 C2 C3 C4 0.3(9) . . . . ?
C2 C3 C4 C5 0.6(10) . . . . ?
C3 C4 C5 C6 -0.8(9) . . . . ?
C4 C5 C6 C1 0.2(8) . . . . ?
C4 C5 C6 C7 180.0(6) . . . . ?
N1 C1 C6 C5 -179.3(5) . . . . ?
C2 C1 C6 C5 0.7(8) . . . . ?
N1 C1 C6 C7 0.8(6) . . . . ?
C2 C1 C6 C7 -179.1(5) . . . . ?
C5 C6 C7 C8 179.7(6) . . . . ?
C1 C6 C7 C8 -0.5(6) . . . . ?
C6 C7 C8 N1 -0.1(6) . . . . ?
C6 C7 C8 C9 -177.6(7) . . . . ?
C1 N1 C8 C7 0.6(6) . . . . ?
C17 N1 C8 C7 -176.6(4) . . . . ?
C1 N1 C8 C9 179.2(4) . . . . ?
C17 N1 C8 C9 1.9(5) . . . . ?
C7 C8 C9 C10 -5.2(13) . . . . ?
N1 C8 C9 C10 177.2(6) . . . . ?
C7 C8 C9 C18 175.6(8) . . . . ?
N1 C8 C9 C18 -2.0(5) . . . . ?
C18 C9 C10 C11 -1.4(7) . . . . ?
C8 C9 C10 C11 179.5(6) . . . . ?
C9 C10 C11 C12 0.4(8) . . . . ?
C10 C11 C12 C13 0.5(7) . . . . ?
C10 C11 C12 C19 -179.1(5) . . . . ?
C11 C12 C13 C18 -0.3(7) . . . . ?
C19 C12 C13 C18 179.3(4) . . . . ?
C11 C12 C13 C14 179.0(5) . . . . ?
C19 C12 C13 C14 -1.4(7) . . . . ?
C18 C13 C14 C15 0.4(7) . . . . ?
C12 C13 C14 C15 -178.9(5) . . . . ?
C18 C13 C14 C20 -178.9(5) . . . . ?
C12 C13 C14 C20 1.8(7) . . . . ?
C13 C14 C15 C16 0.3(8) . . . . ?
C20 C14 C15 C16 179.5(5) . . . . ?
C14 C15 C16 C17 -0.7(8) . . . . ?
C15 C16 C17 N1 -179.4(5) . . . . ?
C15 C16 C17 C18 0.5(7) . . . . ?
C1 N1 C17 C16 2.9(10) . . . . ?
C8 N1 C17 C16 178.9(6) . . . . ?
C1 N1 C17 C18 -177.0(5) . . . . ?
C8 N1 C17 C18 -1.0(5) . . . . ?
C12 C13 C18 C9 -0.8(7) . . . . ?
C14 C13 C18 C9 179.9(5) . . . . ?
C12 C13 C18 C17 178.8(4) . . . . ?
C14 C13 C18 C17 -0.6(7) . . . . ?
C10 C9 C18 C13 1.7(7) . . . . ?
C8 C9 C18 C13 -179.0(5) . . . . ?
C10 C9 C18 C17 -177.9(4) . . . . ?
C8 C9 C18 C17 1.4(5) . . . . ?
C16 C17 C18 C13 0.1(7) . . . . ?
N1 C17 C18 C13 -179.9(4) . . . . ?
C16 C17 C18 C9 179.7(5) . . . . ?
N1 C17 C18 C9 -0.3(5) . . . . ?
C20 N2 C19 O1 -175.6(5) . . . . ?
C21 N2 C19 O1 4.1(7) . . . . ?
C20 N2 C19 C12 5.0(7) . . . . ?
C21 N2 C19 C12 -175.2(4) . . . . ?
C11 C12 C19 O1 -1.5(8) . . . . ?
C13 C12 C19 O1 178.9(5) . . . . ?
C11 C12 C19 N2 177.8(4) . . . . ?
C13 C12 C19 N2 -1.8(6) . . . . ?
C19 N2 C20 O2 175.3(5) . . . . ?
C21 N2 C20 O2 -4.5(7) . . . . ?
C19 N2 C20 C14 -4.7(7) . . . . ?
C21 N2 C20 C14 175.6(4) . . . . ?
C15 C14 C20 O2 1.9(8) . . . . ?
C13 C14 C20 O2 -178.9(5) . . . . ?
C15 C14 C20 N2 -178.2(5) . . . . ?
C13 C14 C20 N2 1.0(7) . . . . ?
C20 N2 C21 C26 89.0(5) . . . . ?
C19 N2 C21 C26 -90.8(5) . . . . ?
C20 N2 C21 C22 -90.2(5) . . . . ?
C19 N2 C21 C22 90.0(5) . . . . ?
C26 C21 C22 C23 0.9(7) . . . . ?
N2 C21 C22 C23 -180.0(5) . . . . ?
C26 C21 C22 C27 -179.6(5) . . . . ?
N2 C21 C22 C27 -0.5(7) . . . . ?
C21 C22 C23 C24 -0.5(8) . . . . ?
C27 C22 C23 C24 -180.0(6) . . . . ?
C22 C23 C24 C25 -0.1(9) . . . . ?
C23 C24 C25 C26 0.3(9) . . . . ?
C22 C21 C26 C25 -0.7(7) . . . . ?
N2 C21 C26 C25 -179.8(4) . . . . ?
C22 C21 C26 C30 179.1(5) . . . . ?
N2 C21 C26 C30 0.0(7) . . . . ?
C24 C25 C26 C21 0.1(8) . . . . ?
C24 C25 C26 C30 -179.7(5) . . . . ?
C23 C22 C27 C29 -61.6(9) . . . . ?
C21 C22 C27 C29 118.9(7) . . . . ?
C23 C22 C27 C28 61.5(8) . . . . ?
C21 C22 C27 C28 -118.0(7) . . . . ?
C21 C26 C30 C31 119.9(6) . . . . ?
C25 C26 C30 C31 -60.3(7) . . . . ?
C21 C26 C30 C32B -88(4) . . . . ?
C25 C26 C30 C32B 92(4) . . . . ?
C21 C26 C30 C32A -115.2(14) . . . . ?
C25 C26 C30 C32A 64.6(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
C7 H7 O2 0.93 2.50 3.199(7) 132.0 1_455

_refine_diff_density_max         0.284
_refine_diff_density_min         -0.446
_refine_diff_density_rms         0.052

_shelxl_version_number           2014-3



####################################################################### 
# 
# 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_WDE0053_10B_0m
_audit_block_doi                 10.5517/ccdc.csd.cc2dcyrh
_database_code_depnum_ccdc_archive 'CCDC 2216027'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/D2CC06978D 2023
loop_
_audit_author_name
_audit_author_address
'Maja Morawiak'
;Institute of Organic Chemistry Polish Academy of Science
Poland
;
_audit_update_record             
;
2022-10-28 deposited with the CCDC.	2023-12-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C42 H32 N4'
_chemical_formula_sum            'C42 H32 N4'
_chemical_formula_weight         592.71

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   10.7776(3)
_cell_length_b                   11.7310(3)
_cell_length_c                   13.5047(3)
_cell_angle_alpha                83.888(2)
_cell_angle_beta                 74.717(2)
_cell_angle_gamma                67.2760(10)
_cell_volume                     1519.17(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3130
_cell_measurement_theta_min      3.39
_cell_measurement_theta_max      70.35

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless-yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.296
_exptl_crystal_F_000             624
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.492
_exptl_crystal_size_mid          0.244
_exptl_crystal_size_min          0.147
_exptl_absorpt_coefficient_mu    0.591
_shelx_estimated_absorpt_T_min   0.760
_shelx_estimated_absorpt_T_max   0.918
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.7600
_exptl_absorpt_correction_T_max  0.9180
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
 One of the faces of the crystal selected for X-ray measurement
 is too short (0.147 mm).
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            24599
_diffrn_reflns_av_unetI/netI     0.0697
_diffrn_reflns_av_R_equivalents  0.0655
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.393
_diffrn_reflns_theta_max         70.348
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.909
_diffrn_measured_fraction_theta_full 0.953
_diffrn_reflns_Laue_measured_fraction_max 0.909
_diffrn_reflns_Laue_measured_fraction_full 0.953
_diffrn_reflns_point_group_measured_fraction_max 0.909
_diffrn_reflns_point_group_measured_fraction_full 0.953
_reflns_number_total             5269
_reflns_number_gt                3130
_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_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)+(0.0703P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5269
_refine_ls_number_parameters     501
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1046
_refine_ls_R_factor_gt           0.0477
_refine_ls_wR_factor_ref         0.1428
_refine_ls_wR_factor_gt          0.1092
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_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
N1 N 0.6545(2) 0.52733(17) 0.62856(14) 0.0423(5) Uani 1 1 d . . . . .
N2 N 0.59916(19) 0.89542(17) 0.31974(13) 0.0422(5) Uani 1 1 d . . . . .
N3 N 0.9110(2) 0.78821(17) 0.06030(14) 0.0419(5) Uani 1 1 d . . . . .
N4 N 0.67345(19) 0.76044(16) 0.03594(13) 0.0374(5) Uani 1 1 d . . . . .
C1 C 0.7538(2) 0.4072(2) 0.60114(18) 0.0409(6) Uani 1 1 d . . . . .
C2 C 0.8240(3) 0.3871(3) 0.4978(2) 0.0558(7) Uani 1 1 d . . . . .
C3 C 0.9271(3) 0.2767(3) 0.4617(2) 0.0623(8) Uani 1 1 d . . . . .
C4 C 0.9649(3) 0.1796(3) 0.5278(3) 0.0643(8) Uani 1 1 d . . . . .
C5 C 0.8929(3) 0.1964(2) 0.6293(2) 0.0588(7) Uani 1 1 d . . . . .
H5 H 0.9166 0.1302 0.6742 0.071 Uiso 1 1 calc R U . . .
C6 C 0.7875(3) 0.3055(2) 0.66843(19) 0.0444(6) Uani 1 1 d . . . . .
C7 C 0.7122(3) 0.3049(2) 0.77824(19) 0.0589(7) Uani 1 1 d . . . . .
H7A H 0.7488 0.3410 0.8195 0.071 Uiso 1 1 calc R U . . .
H7B H 0.7293 0.2200 0.8008 0.071 Uiso 1 1 calc R U . . .
C8 C 0.5557(3) 0.3763(2) 0.7963(2) 0.0542(7) Uani 1 1 d . . . . .
C9 C 0.5223(2) 0.5107(2) 0.80655(18) 0.0423(6) Uani 1 1 d . . . . .
C10 C 0.4407(3) 0.5702(3) 0.89802(19) 0.0531(7) Uani 1 1 d . . . . .
H10 H 0.4029 0.5259 0.9501 0.064 Uiso 1 1 calc R U . . .
C11 C 0.4136(3) 0.6923(3) 0.9147(2) 0.0603(8) Uani 1 1 d . . . . .
H11 H 0.3568 0.7303 0.9763 0.072 Uiso 1 1 calc R U . . .
C12 C 0.4719(3) 0.7565(3) 0.8387(2) 0.0578(7) Uani 1 1 d . . . . .
C13 C 0.5522(3) 0.7007(2) 0.7463(2) 0.0495(7) Uani 1 1 d . . . . .
C14 C 0.5781(2) 0.5771(2) 0.72800(17) 0.0394(6) Uani 1 1 d . . . . .
C15 C 0.6423(2) 0.6201(2) 0.54807(17) 0.0398(6) Uani 1 1 d . . . . .
C16 C 0.7414(3) 0.6720(2) 0.51248(19) 0.0462(7) Uani 1 1 d . . . . .
C17 C 0.7274(3) 0.7622(2) 0.43782(18) 0.0423(6) Uani 1 1 d . . . . .
C18 C 0.6116(2) 0.80446(19) 0.39608(16) 0.0357(6) Uani 1 1 d . . . . .
C19 C 0.5127(3) 0.7506(2) 0.43071(17) 0.0392(6) Uani 1 1 d . . . . .
C20 C 0.5296(3) 0.6590(2) 0.50559(17) 0.0399(6) Uani 1 1 d . . . . .
C21 C 0.6938(2) 0.9579(2) 0.28933(17) 0.0382(6) Uani 1 1 d . . . . .
C22 C 0.6936(3) 1.0404(2) 0.3552(2) 0.0501(7) Uani 1 1 d . . . . .
C23 C 0.7823(3) 1.1036(2) 0.3248(2) 0.0566(8) Uani 1 1 d . . . . .
C24 C 0.8713(3) 1.0839(2) 0.2289(2) 0.0538(7) Uani 1 1 d . . . . .
C25 C 0.8727(3) 1.0015(2) 0.1632(2) 0.0479(7) Uani 1 1 d . . . . .
C26 C 0.7833(2) 0.9371(2) 0.19221(17) 0.0377(6) Uani 1 1 d . . . . .
C27 C 0.7869(2) 0.8488(2) 0.11942(16) 0.0353(5) Uani 1 1 d . . . . .
C28 C 0.6655(2) 0.83440(19) 0.10668(16) 0.0333(5) Uani 1 1 d . . . . .
C29 C 0.5225(2) 0.90684(19) 0.16409(16) 0.0343(5) Uani 1 1 d . . . . .
C30 C 0.4156(3) 0.9478(2) 0.1134(2) 0.0415(6) Uani 1 1 d . . . . .
C31 C 0.2824(3) 1.0180(2) 0.1634(2) 0.0494(7) Uani 1 1 d . . . . .
C32 C 0.2513(3) 1.0486(2) 0.2650(2) 0.0557(7) Uani 1 1 d . . . . .
C33 C 0.3550(3) 1.0076(2) 0.3172(2) 0.0519(7) Uani 1 1 d . . . . .
C34 C 0.4898(2) 0.9363(2) 0.26742(17) 0.0386(6) Uani 1 1 d . . . . .
C35 C 0.9201(2) 0.7104(2) -0.01152(17) 0.0373(6) Uani 1 1 d . . . . .
C36 C 1.0499(3) 0.6439(2) -0.07649(18) 0.0456(6) Uani 1 1 d . . . . .
C37 C 1.0620(2) 0.5676(2) -0.15078(17) 0.0437(6) Uani 1 1 d . . . . .
C38 C 0.9404(3) 0.5553(2) -0.16417(17) 0.0426(6) Uani 1 1 d . . . . .
C39 C 0.8146(3) 0.6184(2) -0.10144(18) 0.0429(6) Uani 1 1 d . . . . .
C40 C 0.8006(2) 0.6971(2) -0.02412(16) 0.0367(6) Uani 1 1 d . . . . .
C41 C 1.2021(3) 0.4971(3) -0.21788(19) 0.0650(8) Uani 1 1 d . . . . .
H41A H 1.2070 0.5283 -0.2869 0.098 Uiso 1 1 calc R U . . .
H41B H 1.2161 0.4111 -0.2171 0.098 Uiso 1 1 calc R U . . .
H41C H 1.2727 0.5067 -0.1925 0.098 Uiso 1 1 calc R U . . .
C42 C 0.9522(3) 0.4727(2) -0.24690(19) 0.0647(8) Uani 1 1 d . . . . .
H42A H 0.8611 0.4822 -0.2510 0.097 Uiso 1 1 calc R U . . .
H42B H 1.0020 0.3882 -0.2309 0.097 Uiso 1 1 calc R U . . .
H42C H 1.0009 0.4949 -0.3116 0.097 Uiso 1 1 calc R U . . .
H17 H 0.798(2) 0.7949(18) 0.4125(14) 0.038(6) Uiso 1 1 d . . . . .
H19 H 0.434(2) 0.7757(18) 0.4036(15) 0.037(6) Uiso 1 1 d . . . . .
H23 H 0.782(2) 1.158(2) 0.3718(18) 0.067(8) Uiso 1 1 d . . . . .
H39 H 0.731(2) 0.612(2) -0.1098(16) 0.057(7) Uiso 1 1 d . . . . .
H22 H 0.626(2) 1.054(2) 0.4230(18) 0.055(7) Uiso 1 1 d . . . . .
H25 H 0.939(2) 0.9869(19) 0.0952(16) 0.045(7) Uiso 1 1 d . . . . .
H31 H 0.211(2) 1.0469(19) 0.1264(16) 0.046(7) Uiso 1 1 d . . . . .
H36 H 1.133(2) 0.653(2) -0.0677(17) 0.058(7) Uiso 1 1 d . . . . .
H4 H 1.037(3) 0.098(3) 0.5044(19) 0.074(9) Uiso 1 1 d . . . . .
H16 H 0.819(2) 0.645(2) 0.5394(16) 0.047(7) Uiso 1 1 d . . . . .
H20 H 0.460(2) 0.6235(18) 0.5306(14) 0.035(6) Uiso 1 1 d . . . . .
H2 H 0.798(3) 0.454(3) 0.450(2) 0.080(9) Uiso 1 1 d . . . . .
H13 H 0.599(2) 0.745(2) 0.6875(18) 0.060(7) Uiso 1 1 d . . . . .
H30 H 0.442(2) 0.925(2) 0.0406(17) 0.055(7) Uiso 1 1 d . . . . .
H3 H 0.974(3) 0.269(2) 0.3882(19) 0.063(8) Uiso 1 1 d . . . . .
H33 H 0.333(2) 1.028(2) 0.3923(19) 0.065(8) Uiso 1 1 d . . . . .
H32 H 0.152(3) 1.102(2) 0.2996(18) 0.072(8) Uiso 1 1 d . . . . .
H8A H 0.507(2) 0.348(2) 0.8597(18) 0.060(7) Uiso 1 1 d . . . . .
H8B H 0.524(2) 0.362(2) 0.7332(18) 0.062(7) Uiso 1 1 d . . . . .
H24 H 0.934(3) 1.128(2) 0.2050(17) 0.064(8) Uiso 1 1 d . . . . .
H12 H 0.459(3) 0.846(2) 0.8467(18) 0.070(8) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C1 1.416(3) . ?
N1 C14 1.426(3) . ?
N1 C15 1.448(3) . ?
N2 C18 1.396(3) . ?
N2 C21 1.428(3) . ?
N2 C34 1.431(3) . ?
N3 C27 1.325(3) . ?
N3 C35 1.361(3) . ?
N4 C28 1.322(2) . ?
N4 C40 1.358(3) . ?
C1 C2 1.397(3) . ?
C1 C6 1.410(3) . ?
C2 C3 1.373(4) . ?
C2 H2 0.96(3) . ?
C3 C4 1.370(4) . ?
C3 H3 0.98(2) . ?
C4 C5 1.377(4) . ?
C4 H4 0.99(3) . ?
C5 C6 1.383(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.492(3) . ?
C7 C8 1.531(4) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.489(3) . ?
C8 H8A 0.98(2) . ?
C8 H8B 1.05(2) . ?
C9 C10 1.387(3) . ?
C9 C14 1.394(3) . ?
C10 C11 1.378(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.370(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.379(3) . ?
C12 H12 1.02(3) . ?
C13 C14 1.403(3) . ?
C13 H13 1.03(2) . ?
C15 C20 1.377(3) . ?
C15 C16 1.383(3) . ?
C16 C17 1.374(3) . ?
C16 H16 0.93(2) . ?
C17 C18 1.398(3) . ?
C17 H17 0.95(2) . ?
C18 C19 1.395(3) . ?
C19 C20 1.387(3) . ?
C19 H19 0.95(2) . ?
C20 H20 0.96(2) . ?
C21 C22 1.381(3) . ?
C21 C26 1.389(3) . ?
C22 C23 1.381(3) . ?
C22 H22 0.99(2) . ?
C23 C24 1.375(4) . ?
C23 H23 0.94(2) . ?
C24 C25 1.373(3) . ?
C24 H24 0.97(2) . ?
C25 C26 1.398(3) . ?
C25 H25 0.99(2) . ?
C26 C27 1.485(3) . ?
C27 C28 1.437(3) . ?
C28 C29 1.482(3) . ?
C29 C34 1.393(3) . ?
C29 C30 1.395(3) . ?
C30 C31 1.374(3) . ?
C30 H30 0.98(2) . ?
C31 C32 1.375(3) . ?
C31 H31 0.96(2) . ?
C32 C33 1.380(4) . ?
C32 H32 1.02(3) . ?
C33 C34 1.389(3) . ?
C33 H33 1.01(2) . ?
C35 C36 1.411(3) . ?
C35 C40 1.411(3) . ?
C36 C37 1.363(3) . ?
C36 H36 0.98(2) . ?
C37 C38 1.431(3) . ?
C37 C41 1.503(3) . ?
C38 C39 1.362(3) . ?
C38 C42 1.505(3) . ?
C39 C40 1.407(3) . ?
C39 H39 0.97(2) . ?
C41 H41A 0.9600 . ?
C41 H41B 0.9600 . ?
C41 H41C 0.9600 . ?
C42 H42A 0.9600 . ?
C42 H42B 0.9600 . ?
C42 H42C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C14 129.21(18) . . ?
C1 N1 C15 116.79(18) . . ?
C14 N1 C15 113.22(18) . . ?
C18 N2 C21 122.18(18) . . ?
C18 N2 C34 123.42(18) . . ?
C21 N2 C34 114.37(17) . . ?
C27 N3 C35 117.89(19) . . ?
C28 N4 C40 117.90(19) . . ?
C2 C1 C6 116.9(2) . . ?
C2 C1 N1 117.1(2) . . ?
C6 C1 N1 126.0(2) . . ?
C3 C2 C1 123.0(3) . . ?
C3 C2 H2 119.0(16) . . ?
C1 C2 H2 118.0(16) . . ?
C4 C3 C2 120.2(3) . . ?
C4 C3 H3 120.8(15) . . ?
C2 C3 H3 119.0(15) . . ?
C3 C4 C5 117.5(3) . . ?
C3 C4 H4 122.4(15) . . ?
C5 C4 H4 120.0(15) . . ?
C4 C5 C6 124.1(3) . . ?
C4 C5 H5 118.0 . . ?
C6 C5 H5 118.0 . . ?
C5 C6 C1 118.2(2) . . ?
C5 C6 C7 117.2(2) . . ?
C1 C6 C7 124.6(2) . . ?
C6 C7 C8 112.9(2) . . ?
C6 C7 H7A 109.0 . . ?
C8 C7 H7A 109.0 . . ?
C6 C7 H7B 109.0 . . ?
C8 C7 H7B 109.0 . . ?
H7A C7 H7B 107.8 . . ?
C9 C8 C7 110.2(2) . . ?
C9 C8 H8A 108.1(14) . . ?
C7 C8 H8A 110.2(14) . . ?
C9 C8 H8B 109.4(13) . . ?
C7 C8 H8B 108.3(13) . . ?
H8A C8 H8B 110.7(19) . . ?
C10 C9 C14 118.9(2) . . ?
C10 C9 C8 119.7(2) . . ?
C14 C9 C8 121.4(2) . . ?
C11 C10 C9 122.5(2) . . ?
C11 C10 H10 118.7 . . ?
C9 C10 H10 118.7 . . ?
C12 C11 C10 118.6(3) . . ?
C12 C11 H11 120.7 . . ?
C10 C11 H11 120.7 . . ?
C11 C12 C13 120.4(3) . . ?
C11 C12 H12 122.9(14) . . ?
C13 C12 H12 116.8(14) . . ?
C12 C13 C14 121.3(3) . . ?
C12 C13 H13 123.0(12) . . ?
C14 C13 H13 115.7(12) . . ?
C9 C14 C13 118.2(2) . . ?
C9 C14 N1 123.2(2) . . ?
C13 C14 N1 118.5(2) . . ?
C20 C15 C16 118.5(2) . . ?
C20 C15 N1 119.9(2) . . ?
C16 C15 N1 121.6(2) . . ?
C17 C16 C15 121.2(2) . . ?
C17 C16 H16 119.7(14) . . ?
C15 C16 H16 119.1(14) . . ?
C16 C17 C18 120.6(2) . . ?
C16 C17 H17 120.1(12) . . ?
C18 C17 H17 119.3(12) . . ?
C19 C18 N2 121.7(2) . . ?
C19 C18 C17 118.2(2) . . ?
N2 C18 C17 120.1(2) . . ?
C20 C19 C18 120.2(2) . . ?
C20 C19 H19 119.1(12) . . ?
C18 C19 H19 120.7(12) . . ?
C15 C20 C19 121.3(2) . . ?
C15 C20 H20 118.6(11) . . ?
C19 C20 H20 120.1(12) . . ?
C22 C21 C26 120.6(2) . . ?
C22 C21 N2 120.1(2) . . ?
C26 C21 N2 119.31(19) . . ?
C21 C22 C23 120.2(3) . . ?
C21 C22 H22 117.4(13) . . ?
C23 C22 H22 122.4(13) . . ?
C24 C23 C22 119.8(3) . . ?
C24 C23 H23 121.6(15) . . ?
C22 C23 H23 118.6(15) . . ?
C25 C24 C23 120.4(3) . . ?
C25 C24 H24 117.9(14) . . ?
C23 C24 H24 121.8(14) . . ?
C24 C25 C26 120.8(3) . . ?
C24 C25 H25 119.2(12) . . ?
C26 C25 H25 120.1(12) . . ?
C21 C26 C25 118.3(2) . . ?
C21 C26 C27 122.1(2) . . ?
C25 C26 C27 119.6(2) . . ?
N3 C27 C28 121.0(2) . . ?
N3 C27 C26 115.06(19) . . ?
C28 C27 C26 123.8(2) . . ?
N4 C28 C27 121.4(2) . . ?
N4 C28 C29 114.68(19) . . ?
C27 C28 C29 123.73(19) . . ?
C34 C29 C30 118.1(2) . . ?
C34 C29 C28 122.7(2) . . ?
C30 C29 C28 119.2(2) . . ?
C31 C30 C29 120.9(2) . . ?
C31 C30 H30 123.2(13) . . ?
C29 C30 H30 115.9(13) . . ?
C30 C31 C32 120.7(3) . . ?
C30 C31 H31 119.3(13) . . ?
C32 C31 H31 120.0(13) . . ?
C31 C32 C33 119.5(3) . . ?
C31 C32 H32 118.9(14) . . ?
C33 C32 H32 121.6(14) . . ?
C32 C33 C34 120.2(3) . . ?
C32 C33 H33 120.5(14) . . ?
C34 C33 H33 119.3(14) . . ?
C33 C34 C29 120.6(2) . . ?
C33 C34 N2 120.9(2) . . ?
C29 C34 N2 118.4(2) . . ?
N3 C35 C36 120.1(2) . . ?
N3 C35 C40 120.9(2) . . ?
C36 C35 C40 118.9(2) . . ?
C37 C36 C35 121.6(2) . . ?
C37 C36 H36 119.4(13) . . ?
C35 C36 H36 119.0(13) . . ?
C36 C37 C38 119.4(2) . . ?
C36 C37 C41 120.1(2) . . ?
C38 C37 C41 120.5(2) . . ?
C39 C38 C37 119.6(2) . . ?
C39 C38 C42 120.5(2) . . ?
C37 C38 C42 119.9(2) . . ?
C38 C39 C40 121.6(2) . . ?
C38 C39 H39 120.9(13) . . ?
C40 C39 H39 117.5(13) . . ?
N4 C40 C39 120.2(2) . . ?
N4 C40 C35 120.9(2) . . ?
C39 C40 C35 118.9(2) . . ?
C37 C41 H41A 109.5 . . ?
C37 C41 H41B 109.5 . . ?
H41A C41 H41B 109.5 . . ?
C37 C41 H41C 109.5 . . ?
H41A C41 H41C 109.5 . . ?
H41B C41 H41C 109.5 . . ?
C38 C42 H42A 109.5 . . ?
C38 C42 H42B 109.5 . . ?
H42A C42 H42B 109.5 . . ?
C38 C42 H42C 109.5 . . ?
H42A C42 H42C 109.5 . . ?
H42B C42 H42C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C14 N1 C1 C2 -173.3(2) . . . . ?
C15 N1 C1 C2 -4.2(3) . . . . ?
C14 N1 C1 C6 7.3(4) . . . . ?
C15 N1 C1 C6 176.4(2) . . . . ?
C6 C1 C2 C3 -3.5(4) . . . . ?
N1 C1 C2 C3 177.0(2) . . . . ?
C1 C2 C3 C4 0.4(4) . . . . ?
C2 C3 C4 C5 2.1(4) . . . . ?
C3 C4 C5 C6 -1.4(4) . . . . ?
C4 C5 C6 C1 -1.7(4) . . . . ?
C4 C5 C6 C7 175.0(2) . . . . ?
C2 C1 C6 C5 4.0(3) . . . . ?
N1 C1 C6 C5 -176.5(2) . . . . ?
C2 C1 C6 C7 -172.4(2) . . . . ?
N1 C1 C6 C7 7.1(4) . . . . ?
C5 C6 C7 C8 -139.1(2) . . . . ?
C1 C6 C7 C8 37.3(3) . . . . ?
C6 C7 C8 C9 -83.2(3) . . . . ?
C7 C8 C9 C10 -117.2(3) . . . . ?
C7 C8 C9 C14 59.0(3) . . . . ?
C14 C9 C10 C11 -0.6(4) . . . . ?
C8 C9 C10 C11 175.7(2) . . . . ?
C9 C10 C11 C12 -1.4(4) . . . . ?
C10 C11 C12 C13 2.1(4) . . . . ?
C11 C12 C13 C14 -0.9(4) . . . . ?
C10 C9 C14 C13 1.8(3) . . . . ?
C8 C9 C14 C13 -174.4(2) . . . . ?
C10 C9 C14 N1 -175.1(2) . . . . ?
C8 C9 C14 N1 8.7(3) . . . . ?
C12 C13 C14 C9 -1.1(4) . . . . ?
C12 C13 C14 N1 176.0(2) . . . . ?
C1 N1 C14 C9 -40.1(3) . . . . ?
C15 N1 C14 C9 150.5(2) . . . . ?
C1 N1 C14 C13 143.0(2) . . . . ?
C15 N1 C14 C13 -26.4(3) . . . . ?
C1 N1 C15 C20 106.1(2) . . . . ?
C14 N1 C15 C20 -83.1(2) . . . . ?
C1 N1 C15 C16 -74.3(3) . . . . ?
C14 N1 C15 C16 96.5(3) . . . . ?
C20 C15 C16 C17 1.2(4) . . . . ?
N1 C15 C16 C17 -178.4(2) . . . . ?
C15 C16 C17 C18 0.3(4) . . . . ?
C21 N2 C18 C19 175.02(19) . . . . ?
C34 N2 C18 C19 -3.3(3) . . . . ?
C21 N2 C18 C17 -6.9(3) . . . . ?
C34 N2 C18 C17 174.8(2) . . . . ?
C16 C17 C18 C19 -1.4(3) . . . . ?
C16 C17 C18 N2 -179.5(2) . . . . ?
N2 C18 C19 C20 179.0(2) . . . . ?
C17 C18 C19 C20 0.9(3) . . . . ?
C16 C15 C20 C19 -1.7(3) . . . . ?
N1 C15 C20 C19 177.9(2) . . . . ?
C18 C19 C20 C15 0.7(3) . . . . ?
C18 N2 C21 C22 -69.8(3) . . . . ?
C34 N2 C21 C22 108.6(2) . . . . ?
C18 N2 C21 C26 111.7(2) . . . . ?
C34 N2 C21 C26 -69.9(3) . . . . ?
C26 C21 C22 C23 0.3(4) . . . . ?
N2 C21 C22 C23 -178.2(2) . . . . ?
C21 C22 C23 C24 -0.2(4) . . . . ?
C22 C23 C24 C25 -0.2(4) . . . . ?
C23 C24 C25 C26 0.5(4) . . . . ?
C22 C21 C26 C25 0.0(3) . . . . ?
N2 C21 C26 C25 178.5(2) . . . . ?
C22 C21 C26 C27 179.8(2) . . . . ?
N2 C21 C26 C27 -1.8(3) . . . . ?
C24 C25 C26 C21 -0.4(4) . . . . ?
C24 C25 C26 C27 179.8(2) . . . . ?
C35 N3 C27 C28 -1.1(3) . . . . ?
C35 N3 C27 C26 -176.84(18) . . . . ?
C21 C26 C27 N3 -145.2(2) . . . . ?
C25 C26 C27 N3 34.5(3) . . . . ?
C21 C26 C27 C28 39.2(3) . . . . ?
C25 C26 C27 C28 -141.1(2) . . . . ?
C40 N4 C28 C27 0.6(3) . . . . ?
C40 N4 C28 C29 175.90(17) . . . . ?
N3 C27 C28 N4 0.1(3) . . . . ?
C26 C27 C28 N4 175.41(19) . . . . ?
N3 C27 C28 C29 -174.77(18) . . . . ?
C26 C27 C28 C29 0.6(3) . . . . ?
N4 C28 C29 C34 145.6(2) . . . . ?
C27 C28 C29 C34 -39.3(3) . . . . ?
N4 C28 C29 C30 -34.5(3) . . . . ?
C27 C28 C29 C30 140.7(2) . . . . ?
C34 C29 C30 C31 1.7(3) . . . . ?
C28 C29 C30 C31 -178.3(2) . . . . ?
C29 C30 C31 C32 -0.5(4) . . . . ?
C30 C31 C32 C33 -0.5(4) . . . . ?
C31 C32 C33 C34 0.3(4) . . . . ?
C32 C33 C34 C29 0.9(4) . . . . ?
C32 C33 C34 N2 178.5(2) . . . . ?
C30 C29 C34 C33 -1.9(3) . . . . ?
C28 C29 C34 C33 178.1(2) . . . . ?
C30 C29 C34 N2 -179.53(19) . . . . ?
C28 C29 C34 N2 0.4(3) . . . . ?
C18 N2 C34 C33 71.5(3) . . . . ?
C21 N2 C34 C33 -107.0(2) . . . . ?
C18 N2 C34 C29 -110.9(2) . . . . ?
C21 N2 C34 C29 70.7(2) . . . . ?
C27 N3 C35 C36 179.9(2) . . . . ?
C27 N3 C35 C40 1.5(3) . . . . ?
N3 C35 C36 C37 -178.4(2) . . . . ?
C40 C35 C36 C37 0.0(3) . . . . ?
C35 C36 C37 C38 0.7(4) . . . . ?
C35 C36 C37 C41 -179.3(2) . . . . ?
C36 C37 C38 C39 -1.1(3) . . . . ?
C41 C37 C38 C39 178.9(2) . . . . ?
C36 C37 C38 C42 179.1(2) . . . . ?
C41 C37 C38 C42 -0.8(3) . . . . ?
C37 C38 C39 C40 0.8(3) . . . . ?
C42 C38 C39 C40 -179.4(2) . . . . ?
C28 N4 C40 C39 -179.16(19) . . . . ?
C28 N4 C40 C35 -0.3(3) . . . . ?
C38 C39 C40 N4 178.8(2) . . . . ?
C38 C39 C40 C35 -0.1(3) . . . . ?
N3 C35 C40 N4 -0.8(3) . . . . ?
C36 C35 C40 N4 -179.26(19) . . . . ?
N3 C35 C40 C39 178.1(2) . . . . ?
C36 C35 C40 C39 -0.3(3) . . . . ?

_refine_diff_density_max         0.277
_refine_diff_density_min         -0.257
_refine_diff_density_rms         0.054

_shelxl_version_number           2014-3



####################################################################### 
# 
# 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_KBA0263_A_0m
_database_code_depnum_ccdc_archive 'CCDC 2290710'
loop_
_audit_author_name
_audit_author_address
'Maja Morawiak'
;Institute of Organic Chemistry Polish Academy of Science
Poland
;
_audit_update_record             
;
2023-08-25 deposited with the CCDC.	2023-12-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C44 H33 N3 O3, 2(C H2 Cl2)'
_chemical_formula_sum            'C46 H37 Cl4 N3 O3'
_chemical_formula_weight         821.58

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

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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'

_cell_length_a                   8.696(3)
_cell_length_b                   15.535(5)
_cell_length_c                   15.750(5)
_cell_angle_alpha                90
_cell_angle_beta                 91.87(2)
_cell_angle_gamma                90
_cell_volume                     2126.6(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3786
_cell_measurement_theta_min      2.81
_cell_measurement_theta_max      68.72

_exptl_crystal_description       prism
_exptl_crystal_colour            violet-black
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.283
_exptl_crystal_F_000             852
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.315
_exptl_crystal_size_mid          0.270
_exptl_crystal_size_min          0.264
_exptl_absorpt_coefficient_mu    2.873
_shelx_estimated_absorpt_T_min   0.465
_shelx_estimated_absorpt_T_max   0.518
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.4650
_exptl_absorpt_correction_T_max  0.5180
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
 Crystal selected for X-ray experiment was thin prism
 with dimensions 0.315 mm x 0.270 mm x 0.264 mm.
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            36641
_diffrn_reflns_av_unetI/netI     0.0863
_diffrn_reflns_av_R_equivalents  0.0698
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.807
_diffrn_reflns_theta_max         68.716
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.851
_diffrn_measured_fraction_theta_full 0.864
_diffrn_reflns_Laue_measured_fraction_max 0.851
_diffrn_reflns_Laue_measured_fraction_full 0.864
_diffrn_reflns_point_group_measured_fraction_max 0.852
_diffrn_reflns_point_group_measured_fraction_full 0.865
_reflns_number_total             5893
_reflns_number_gt                3786
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.925
_reflns_Friedel_fraction_max     0.853
_reflns_Friedel_fraction_full    0.866

_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1207P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_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 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.26(8)
_chemical_absolute_configuration rm
_refine_ls_number_reflns         5893
_refine_ls_number_parameters     510
_refine_ls_number_restraints     5
_refine_ls_R_factor_all          0.1170
_refine_ls_R_factor_gt           0.0633
_refine_ls_wR_factor_ref         0.1911
_refine_ls_wR_factor_gt          0.1696
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_restrained_S_all      1.018
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.001

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 0.8076(5) -0.0689(3) 0.2995(3) 0.0659(12) Uani 1 1 d . . . . .
O2 O 0.5113(5) -0.0308(3) 0.0594(3) 0.0655(12) Uani 1 1 d . . . . .
O3 O 1.3523(6) 0.4587(4) 0.3953(3) 0.0975(19) Uani 1 1 d . . . . .
N1 N 0.8751(5) 0.3292(3) 0.1040(3) 0.0432(12) Uani 1 1 d . . . . .
N2 N 0.6582(5) -0.0471(3) 0.1806(3) 0.0444(12) Uani 1 1 d . . . . .
N3 N 1.1520(5) 0.4152(3) 0.2586(3) 0.0503(13) Uani 1 1 d . . . . .
C1 C 0.9017(6) 0.4081(4) 0.0661(3) 0.0421(14) Uani 1 1 d . . . . .
C2 C 0.8405(6) 0.4434(4) -0.0078(4) 0.0488(15) Uani 1 1 d . . . . .
H2 H 0.7688 0.4138 -0.0418 0.059 Uiso 1 1 calc R U . . .
C3 C 0.8899(7) 0.5244(4) -0.0290(4) 0.0599(17) Uani 1 1 d . . . . .
H3 H 0.8513 0.5499 -0.0787 0.072 Uiso 1 1 calc R U . . .
C4 C 0.9957(8) 0.5687(4) 0.0217(4) 0.0596(17) Uani 1 1 d . . . . .
H4 H 1.0264 0.6234 0.0053 0.072 Uiso 1 1 calc R U . . .
C5 C 1.0569(7) 0.5343(4) 0.0958(4) 0.0540(16) Uani 1 1 d . . . . .
H5 H 1.1268 0.5654 0.1296 0.065 Uiso 1 1 calc R U . . .
C6 C 1.0118(6) 0.4518(4) 0.1191(4) 0.0460(15) Uani 1 1 d . . . . .
C7 C 1.0506(6) 0.3961(4) 0.1893(3) 0.0445(15) Uani 1 1 d . . . . .
C8 C 0.9671(6) 0.3211(4) 0.1778(4) 0.0466(15) Uani 1 1 d . . . . .
C9 C 0.9392(6) 0.2360(4) 0.2122(3) 0.0429(14) Uani 1 1 d . . . . .
C10 C 0.9876(6) 0.1885(4) 0.2835(4) 0.0536(16) Uani 1 1 d . . . . .
H10 H 1.0567 0.2113 0.3238 0.064 Uiso 1 1 calc R U . . .
C11 C 0.9276(7) 0.1045(4) 0.2922(4) 0.0522(16) Uani 1 1 d . . . . .
H11 H 0.9572 0.0727 0.3400 0.063 Uiso 1 1 calc R U . . .
C12 C 0.8282(6) 0.0678(4) 0.2338(3) 0.0421(14) Uani 1 1 d . . . . .
C13 C 0.7759(7) 0.1159(4) 0.1631(3) 0.0427(14) Uani 1 1 d . . . . .
C14 C 0.6675(7) 0.0878(4) 0.1008(3) 0.0429(14) Uani 1 1 d . . . . .
C15 C 0.6268(7) 0.1426(4) 0.0358(4) 0.0523(16) Uani 1 1 d . . . . .
H15 H 0.5558 0.1232 -0.0053 0.063 Uiso 1 1 calc R U . . .
C16 C 0.6856(6) 0.2265(4) 0.0271(4) 0.0453(15) Uani 1 1 d . . . . .
H16 H 0.6550 0.2619 -0.0180 0.054 Uiso 1 1 calc R U . . .
C17 C 0.7910(6) 0.2535(4) 0.0889(3) 0.0419(14) Uani 1 1 d . . . . .
C18 C 0.8349(6) 0.1991(4) 0.1551(3) 0.0427(14) Uani 1 1 d . . . . .
C19 C 0.7686(7) -0.0203(4) 0.2418(4) 0.0487(15) Uani 1 1 d . . . . .
C20 C 0.6049(7) 0.0002(4) 0.1094(4) 0.0488(16) Uani 1 1 d . . . . .
C21 C 0.5952(7) -0.1323(4) 0.1892(4) 0.0494(15) Uani 1 1 d . . . . .
C22 C 0.6601(7) -0.2014(4) 0.1460(4) 0.0546(16) Uani 1 1 d . . . . .
C23 C 0.5966(8) -0.2816(4) 0.1576(4) 0.0667(19) Uani 1 1 d . . . . .
H23 H 0.6384 -0.3290 0.1307 0.080 Uiso 1 1 calc R U . . .
C24 C 0.4724(9) -0.2930(5) 0.2085(5) 0.076(2) Uani 1 1 d . . . . .
H24 H 0.4304 -0.3476 0.2145 0.092 Uiso 1 1 calc R U . . .
C25 C 0.4119(8) -0.2265(5) 0.2491(5) 0.073(2) Uani 1 1 d . . . . .
H25 H 0.3273 -0.2354 0.2826 0.087 Uiso 1 1 calc R U . . .
C26 C 0.4726(8) -0.1440(4) 0.2425(4) 0.0612(18) Uani 1 1 d . . . . .
C27 C 0.7948(8) -0.1901(4) 0.0895(5) 0.0683(19) Uani 1 1 d . . . . .
H27 H 0.8083 -0.1282 0.0803 0.082 Uiso 1 1 calc R U . . .
C28 C 0.7659(8) -0.2314(5) 0.0035(4) 0.079(2) Uani 1 1 d . . . . .
H28A H 0.7649 -0.2929 0.0097 0.118 Uiso 1 1 calc R U . . .
H28B H 0.8461 -0.2152 -0.0338 0.118 Uiso 1 1 calc R U . . .
H28C H 0.6685 -0.2125 -0.0199 0.118 Uiso 1 1 calc R U . . .
C29 C 0.9405(8) -0.2235(6) 0.1323(5) 0.089(2) Uani 1 1 d . . . . .
H29A H 0.9249 -0.2817 0.1504 0.133 Uiso 1 1 calc R U . . .
H29B H 0.9668 -0.1882 0.1807 0.133 Uiso 1 1 calc R U . . .
H29C H 1.0225 -0.2218 0.0930 0.133 Uiso 1 1 calc R U . . .
C30 C 0.3997(9) -0.0700(5) 0.2912(5) 0.082(2) Uani 1 1 d . . . . .
H30 H 0.4599 -0.0180 0.2806 0.098 Uiso 1 1 calc R U . . .
C31 C 0.4097(12) -0.0875(8) 0.3867(5) 0.127(4) Uani 1 1 d . . . . .
H31A H 0.3917 -0.0350 0.4170 0.191 Uiso 1 1 calc R U . . .
H31B H 0.5102 -0.1091 0.4021 0.191 Uiso 1 1 calc R U . . .
H31C H 0.3335 -0.1293 0.4010 0.191 Uiso 1 1 calc R U . . .
C32 C 0.2405(12) -0.0530(8) 0.2623(6) 0.143(4) Uani 1 1 d . . . . .
H32A H 0.1917 -0.1061 0.2459 0.214 Uiso 1 1 calc R U . . .
H32B H 0.2403 -0.0146 0.2145 0.214 Uiso 1 1 calc R U . . .
H32C H 0.1855 -0.0271 0.3076 0.214 Uiso 1 1 calc R U . . .
C33 C 1.3060(6) 0.4365(4) 0.2444(4) 0.0456(15) Uani 1 1 d . . . . .
C34 C 1.3690(7) 0.4330(4) 0.1652(4) 0.0600(18) Uani 1 1 d . . . . .
H34 H 1.3079 0.4163 0.1185 0.072 Uiso 1 1 calc R U . . .
C35 C 1.5210(7) 0.4539(5) 0.1541(5) 0.0682(19) Uani 1 1 d . . . . .
H35 H 1.5614 0.4524 0.1002 0.082 Uiso 1 1 calc R U . . .
C36 C 1.6117(7) 0.4768(5) 0.2224(5) 0.075(2) Uani 1 1 d . . . . .
H36 H 1.7139 0.4917 0.2148 0.090 Uiso 1 1 calc R U . . .
C37 C 1.5539(8) 0.4782(5) 0.3016(5) 0.075(2) Uani 1 1 d . . . . .
H37 H 1.6171 0.4927 0.3482 0.090 Uiso 1 1 calc R U . . .
C38 C 1.4009(7) 0.4579(4) 0.3127(4) 0.0601(17) Uani 1 1 d . . . . .
C39 C 1.2014(7) 0.4367(5) 0.4083(4) 0.0602(18) Uani 1 1 d . . . . .
C40 C 1.1605(9) 0.4383(6) 0.4900(4) 0.083(2) Uani 1 1 d . . . . .
H40 H 1.2326 0.4513 0.5331 0.099 Uiso 1 1 calc R U . . .
C41 C 1.0120(10) 0.4206(6) 0.5087(5) 0.090(3) Uani 1 1 d . . . . .
H41 H 0.9821 0.4232 0.5648 0.108 Uiso 1 1 calc R U . . .
C42 C 0.9074(9) 0.3995(5) 0.4468(5) 0.084(2) Uani 1 1 d . . . . .
H42 H 0.8068 0.3864 0.4604 0.101 Uiso 1 1 calc R U . . .
C43 C 0.9512(8) 0.3974(5) 0.3627(4) 0.0666(19) Uani 1 1 d . . . . .
H43 H 0.8794 0.3830 0.3199 0.080 Uiso 1 1 calc R U . . .
C44 C 1.0998(6) 0.4162(4) 0.3422(3) 0.0461(15) Uani 1 1 d . . . . .
Cl1 Cl 0.4224(19) 0.2042(9) 0.2612(15) 0.614(16) Uani 1 1 d D . . . .
Cl2 Cl 0.5897(18) 0.190(2) 0.410(2) 0.82(3) Uani 1 1 d D . . . .
Cl4 Cl 0.184(4) 0.1729(12) 0.5358(9) 0.93(3) Uani 1 1 d D . . . .
C51 C 0.409(3) 0.188(4) 0.3696(19) 0.52(4) Uani 1 1 d D . . . .
H51A H 0.3477 0.2326 0.3947 0.623 Uiso 1 1 calc R U . . .
H51B H 0.3611 0.1325 0.3806 0.623 Uiso 1 1 calc R U . . .
C52 C 0.144(3) 0.169(2) 0.6413(12) 0.41(3) Uani 1 1 d D . . . .
H52A H 0.1807 0.2201 0.6710 0.493 Uiso 1 1 calc R U . . .
H52B H 0.1892 0.1185 0.6684 0.493 Uiso 1 1 calc R U . . .
Cl3 Cl -0.053(3) 0.1637(13) 0.639(2) 0.744(18) Uani 1 1 d D . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C19 1.221(7) . ?
O2 C20 1.214(7) . ?
O3 C39 1.378(8) . ?
O3 C38 1.381(8) . ?
N1 C1 1.386(7) . ?
N1 C8 1.395(7) . ?
N1 C17 1.401(7) . ?
N2 C19 1.401(7) . ?
N2 C20 1.407(7) . ?
N2 C21 1.440(8) . ?
N3 C33 1.404(7) . ?
N3 C44 1.408(7) . ?
N3 C7 1.411(7) . ?
C1 C2 1.378(8) . ?
C1 C6 1.422(8) . ?
C2 C3 1.373(8) . ?
C2 H2 0.9300 . ?
C3 C4 1.383(9) . ?
C3 H3 0.9300 . ?
C4 C5 1.375(9) . ?
C4 H4 0.9300 . ?
C5 C6 1.394(8) . ?
C5 H5 0.9300 . ?
C6 C7 1.435(8) . ?
C7 C8 1.382(8) . ?
C8 C9 1.452(8) . ?
C9 C18 1.382(7) . ?
C9 C10 1.397(8) . ?
C10 C11 1.413(9) . ?
C10 H10 0.9300 . ?
C11 C12 1.366(7) . ?
C11 H11 0.9300 . ?
C12 C13 1.405(7) . ?
C12 C19 1.470(8) . ?
C13 C18 1.397(8) . ?
C13 C14 1.407(8) . ?
C14 C15 1.369(8) . ?
C14 C20 1.474(8) . ?
C15 C16 1.408(8) . ?
C15 H15 0.9300 . ?
C16 C17 1.380(8) . ?
C16 H16 0.9300 . ?
C17 C18 1.386(8) . ?
C21 C26 1.390(9) . ?
C21 C22 1.400(9) . ?
C22 C23 1.377(9) . ?
C22 C27 1.504(9) . ?
C23 C24 1.376(10) . ?
C23 H23 0.9300 . ?
C24 C25 1.333(10) . ?
C24 H24 0.9300 . ?
C25 C26 1.390(10) . ?
C25 H25 0.9300 . ?
C26 C30 1.532(10) . ?
C27 C29 1.507(10) . ?
C27 C28 1.512(9) . ?
C27 H27 0.9800 . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?
C29 H29A 0.9600 . ?
C29 H29B 0.9600 . ?
C29 H29C 0.9600 . ?
C30 C32 1.467(11) . ?
C30 C31 1.527(11) . ?
C30 H30 0.9800 . ?
C31 H31A 0.9600 . ?
C31 H31B 0.9600 . ?
C31 H31C 0.9600 . ?
C32 H32A 0.9600 . ?
C32 H32B 0.9600 . ?
C32 H32C 0.9600 . ?
C33 C38 1.375(8) . ?
C33 C34 1.380(8) . ?
C34 C35 1.377(8) . ?
C34 H34 0.9300 . ?
C35 C36 1.360(9) . ?
C35 H35 0.9300 . ?
C36 C37 1.361(10) . ?
C36 H36 0.9300 . ?
C37 C38 1.384(9) . ?
C37 H37 0.9300 . ?
C39 C40 1.346(8) . ?
C39 C44 1.380(8) . ?
C40 C41 1.362(10) . ?
C40 H40 0.9300 . ?
C41 C42 1.352(10) . ?
C41 H41 0.9300 . ?
C42 C43 1.391(9) . ?
C42 H42 0.9300 . ?
C43 C44 1.374(8) . ?
C43 H43 0.9300 . ?
Cl1 C51 1.74(2) . ?
Cl2 C51 1.68(2) . ?
Cl4 C52 1.71(2) . ?
C51 H51A 0.9700 . ?
C51 H51B 0.9700 . ?
C52 Cl3 1.71(2) . ?
C52 H52A 0.9700 . ?
C52 H52B 0.9700 . ?

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
C39 O3 C38 117.4(5) . . ?
C1 N1 C8 109.8(4) . . ?
C1 N1 C17 139.7(5) . . ?
C8 N1 C17 110.4(5) . . ?
C19 N2 C20 126.4(5) . . ?
C19 N2 C21 117.6(5) . . ?
C20 N2 C21 116.0(5) . . ?
C33 N3 C44 119.0(4) . . ?
C33 N3 C7 120.1(4) . . ?
C44 N3 C7 120.9(4) . . ?
C2 C1 N1 130.6(5) . . ?
C2 C1 C6 122.7(6) . . ?
N1 C1 C6 106.7(5) . . ?
C3 C2 C1 117.1(6) . . ?
C3 C2 H2 121.5 . . ?
C1 C2 H2 121.5 . . ?
C2 C3 C4 121.5(6) . . ?
C2 C3 H3 119.2 . . ?
C4 C3 H3 119.2 . . ?
C5 C4 C3 121.9(6) . . ?
C5 C4 H4 119.0 . . ?
C3 C4 H4 119.0 . . ?
C4 C5 C6 118.5(6) . . ?
C4 C5 H5 120.7 . . ?
C6 C5 H5 120.7 . . ?
C5 C6 C1 118.3(6) . . ?
C5 C6 C7 134.1(6) . . ?
C1 C6 C7 107.6(5) . . ?
C8 C7 N3 126.2(5) . . ?
C8 C7 C6 107.3(5) . . ?
N3 C7 C6 126.4(5) . . ?
C7 C8 N1 108.6(5) . . ?
C7 C8 C9 144.3(6) . . ?
N1 C8 C9 107.1(5) . . ?
C18 C9 C10 118.5(6) . . ?
C18 C9 C8 104.4(5) . . ?
C10 C9 C8 137.0(5) . . ?
C9 C10 C11 117.6(5) . . ?
C9 C10 H10 121.2 . . ?
C11 C10 H10 121.2 . . ?
C12 C11 C10 123.2(6) . . ?
C12 C11 H11 118.4 . . ?
C10 C11 H11 118.4 . . ?
C11 C12 C13 119.6(5) . . ?
C11 C12 C19 123.2(5) . . ?
C13 C12 C19 117.2(5) . . ?
C18 C13 C12 116.9(5) . . ?
C18 C13 C14 117.6(5) . . ?
C12 C13 C14 125.4(5) . . ?
C15 C14 C13 118.6(5) . . ?
C15 C14 C20 123.8(5) . . ?
C13 C14 C20 117.6(5) . . ?
C14 C15 C16 124.2(5) . . ?
C14 C15 H15 117.9 . . ?
C16 C15 H15 117.9 . . ?
C17 C16 C15 116.6(5) . . ?
C17 C16 H16 121.7 . . ?
C15 C16 H16 121.7 . . ?
C16 C17 C18 120.3(5) . . ?
C16 C17 N1 134.9(5) . . ?
C18 C17 N1 104.8(5) . . ?
C9 C18 C17 113.3(5) . . ?
C9 C18 C13 124.1(5) . . ?
C17 C18 C13 122.6(5) . . ?
O1 C19 N2 119.6(6) . . ?
O1 C19 C12 123.4(5) . . ?
N2 C19 C12 117.0(5) . . ?
O2 C20 N2 120.4(5) . . ?
O2 C20 C14 123.3(6) . . ?
N2 C20 C14 116.3(6) . . ?
C26 C21 C22 121.5(6) . . ?
C26 C21 N2 118.6(5) . . ?
C22 C21 N2 119.9(5) . . ?
C23 C22 C21 117.3(5) . . ?
C23 C22 C27 120.5(6) . . ?
C21 C22 C27 122.1(5) . . ?
C24 C23 C22 121.3(7) . . ?
C24 C23 H23 119.4 . . ?
C22 C23 H23 119.4 . . ?
C25 C24 C23 120.6(7) . . ?
C25 C24 H24 119.7 . . ?
C23 C24 H24 119.7 . . ?
C24 C25 C26 121.4(6) . . ?
C24 C25 H25 119.3 . . ?
C26 C25 H25 119.3 . . ?
C21 C26 C25 117.8(6) . . ?
C21 C26 C30 122.8(6) . . ?
C25 C26 C30 119.3(6) . . ?
C22 C27 C29 110.8(6) . . ?
C22 C27 C28 111.7(5) . . ?
C29 C27 C28 111.5(6) . . ?
C22 C27 H27 107.5 . . ?
C29 C27 H27 107.5 . . ?
C28 C27 H27 107.5 . . ?
C27 C28 H28A 109.5 . . ?
C27 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C27 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C27 C29 H29A 109.5 . . ?
C27 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C27 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C32 C30 C31 111.1(7) . . ?
C32 C30 C26 112.4(7) . . ?
C31 C30 C26 110.5(7) . . ?
C32 C30 H30 107.5 . . ?
C31 C30 H30 107.5 . . ?
C26 C30 H30 107.5 . . ?
C30 C31 H31A 109.5 . . ?
C30 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
C30 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C30 C32 H32A 109.5 . . ?
C30 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
C30 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C38 C33 C34 118.1(5) . . ?
C38 C33 N3 118.9(5) . . ?
C34 C33 N3 122.9(5) . . ?
C35 C34 C33 121.1(6) . . ?
C35 C34 H34 119.5 . . ?
C33 C34 H34 119.5 . . ?
C36 C35 C34 119.7(6) . . ?
C36 C35 H35 120.1 . . ?
C34 C35 H35 120.1 . . ?
C35 C36 C37 120.5(6) . . ?
C35 C36 H36 119.8 . . ?
C37 C36 H36 119.8 . . ?
C36 C37 C38 119.8(6) . . ?
C36 C37 H37 120.1 . . ?
C38 C37 H37 120.1 . . ?
C33 C38 O3 123.0(5) . . ?
C33 C38 C37 120.8(6) . . ?
O3 C38 C37 116.2(6) . . ?
C40 C39 O3 114.8(6) . . ?
C40 C39 C44 122.9(6) . . ?
O3 C39 C44 122.3(5) . . ?
C39 C40 C41 118.9(7) . . ?
C39 C40 H40 120.5 . . ?
C41 C40 H40 120.5 . . ?
C42 C41 C40 120.9(6) . . ?
C42 C41 H41 119.5 . . ?
C40 C41 H41 119.5 . . ?
C41 C42 C43 119.6(7) . . ?
C41 C42 H42 120.2 . . ?
C43 C42 H42 120.2 . . ?
C44 C43 C42 120.5(6) . . ?
C44 C43 H43 119.8 . . ?
C42 C43 H43 119.8 . . ?
C43 C44 C39 117.1(5) . . ?
C43 C44 N3 123.5(5) . . ?
C39 C44 N3 119.4(5) . . ?
Cl2 C51 Cl1 106(2) . . ?
Cl2 C51 H51A 110.5 . . ?
Cl1 C51 H51A 110.5 . . ?
Cl2 C51 H51B 110.5 . . ?
Cl1 C51 H51B 110.5 . . ?
H51A C51 H51B 108.7 . . ?
Cl4 C52 Cl3 102.5(18) . . ?
Cl4 C52 H52A 111.3 . . ?
Cl3 C52 H52A 111.3 . . ?
Cl4 C52 H52B 111.3 . . ?
Cl3 C52 H52B 111.3 . . ?
H52A C52 H52B 109.2 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C8 N1 C1 C2 178.6(5) . . . . ?
C17 N1 C1 C2 3.2(10) . . . . ?
C8 N1 C1 C6 -1.4(5) . . . . ?
C17 N1 C1 C6 -176.7(5) . . . . ?
N1 C1 C2 C3 179.8(5) . . . . ?
C6 C1 C2 C3 -0.2(8) . . . . ?
C1 C2 C3 C4 -0.4(8) . . . . ?
C2 C3 C4 C5 0.0(9) . . . . ?
C3 C4 C5 C6 0.9(9) . . . . ?
C4 C5 C6 C1 -1.5(8) . . . . ?
C4 C5 C6 C7 179.4(6) . . . . ?
C2 C1 C6 C5 1.2(7) . . . . ?
N1 C1 C6 C5 -178.8(4) . . . . ?
C2 C1 C6 C7 -179.5(5) . . . . ?
N1 C1 C6 C7 0.5(6) . . . . ?
C33 N3 C7 C8 123.1(6) . . . . ?
C44 N3 C7 C8 -59.2(8) . . . . ?
C33 N3 C7 C6 -58.8(7) . . . . ?
C44 N3 C7 C6 118.9(6) . . . . ?
C5 C6 C7 C8 179.8(5) . . . . ?
C1 C6 C7 C8 0.6(6) . . . . ?
C5 C6 C7 N3 1.3(9) . . . . ?
C1 C6 C7 N3 -177.8(5) . . . . ?
N3 C7 C8 N1 177.0(5) . . . . ?
C6 C7 C8 N1 -1.5(6) . . . . ?
N3 C7 C8 C9 -4.3(12) . . . . ?
C6 C7 C8 C9 177.3(7) . . . . ?
C1 N1 C8 C7 1.8(6) . . . . ?
C17 N1 C8 C7 178.6(4) . . . . ?
C1 N1 C8 C9 -177.4(4) . . . . ?
C17 N1 C8 C9 -0.6(6) . . . . ?
C7 C8 C9 C18 -177.5(7) . . . . ?
N1 C8 C9 C18 1.3(6) . . . . ?
C7 C8 C9 C10 3.6(14) . . . . ?
N1 C8 C9 C10 -177.6(6) . . . . ?
C18 C9 C10 C11 0.8(8) . . . . ?
C8 C9 C10 C11 179.6(6) . . . . ?
C9 C10 C11 C12 1.4(9) . . . . ?
C10 C11 C12 C13 -3.1(8) . . . . ?
C10 C11 C12 C19 178.5(5) . . . . ?
C11 C12 C13 C18 2.5(8) . . . . ?
C19 C12 C13 C18 -179.0(5) . . . . ?
C11 C12 C13 C14 -176.4(5) . . . . ?
C19 C12 C13 C14 2.1(8) . . . . ?
C18 C13 C14 C15 0.5(8) . . . . ?
C12 C13 C14 C15 179.4(5) . . . . ?
C18 C13 C14 C20 -179.7(5) . . . . ?
C12 C13 C14 C20 -0.9(8) . . . . ?
C13 C14 C15 C16 -0.5(9) . . . . ?
C20 C14 C15 C16 179.7(5) . . . . ?
C14 C15 C16 C17 0.1(8) . . . . ?
C15 C16 C17 C18 0.3(8) . . . . ?
C15 C16 C17 N1 179.9(5) . . . . ?
C1 N1 C17 C16 -4.6(11) . . . . ?
C8 N1 C17 C16 -179.9(6) . . . . ?
C1 N1 C17 C18 175.1(6) . . . . ?
C8 N1 C17 C18 -0.3(5) . . . . ?
C10 C9 C18 C17 177.6(5) . . . . ?
C8 C9 C18 C17 -1.6(6) . . . . ?
C10 C9 C18 C13 -1.2(8) . . . . ?
C8 C9 C18 C13 179.6(5) . . . . ?
C16 C17 C18 C9 -179.1(5) . . . . ?
N1 C17 C18 C9 1.2(6) . . . . ?
C16 C17 C18 C13 -0.3(8) . . . . ?
N1 C17 C18 C13 -180.0(5) . . . . ?
C12 C13 C18 C9 -0.4(8) . . . . ?
C14 C13 C18 C9 178.6(5) . . . . ?
C12 C13 C18 C17 -179.1(5) . . . . ?
C14 C13 C18 C17 -0.1(8) . . . . ?
C20 N2 C19 O1 -178.1(5) . . . . ?
C21 N2 C19 O1 0.0(7) . . . . ?
C20 N2 C19 C12 3.8(7) . . . . ?
C21 N2 C19 C12 -178.1(5) . . . . ?
C11 C12 C19 O1 -2.9(8) . . . . ?
C13 C12 C19 O1 178.6(5) . . . . ?
C11 C12 C19 N2 175.1(5) . . . . ?
C13 C12 C19 N2 -3.4(7) . . . . ?
C19 N2 C20 O2 178.0(5) . . . . ?
C21 N2 C20 O2 -0.1(7) . . . . ?
C19 N2 C20 C14 -2.6(7) . . . . ?
C21 N2 C20 C14 179.3(5) . . . . ?
C15 C14 C20 O2 0.0(9) . . . . ?
C13 C14 C20 O2 -179.7(5) . . . . ?
C15 C14 C20 N2 -179.4(5) . . . . ?
C13 C14 C20 N2 0.9(7) . . . . ?
C19 N2 C21 C26 84.4(6) . . . . ?
C20 N2 C21 C26 -97.4(6) . . . . ?
C19 N2 C21 C22 -93.9(6) . . . . ?
C20 N2 C21 C22 84.3(6) . . . . ?
C26 C21 C22 C23 0.7(9) . . . . ?
N2 C21 C22 C23 178.9(6) . . . . ?
C26 C21 C22 C27 -178.7(6) . . . . ?
N2 C21 C22 C27 -0.4(9) . . . . ?
C21 C22 C23 C24 1.2(10) . . . . ?
C27 C22 C23 C24 -179.4(6) . . . . ?
C22 C23 C24 C25 -1.2(11) . . . . ?
C23 C24 C25 C26 -0.8(11) . . . . ?
C22 C21 C26 C25 -2.5(9) . . . . ?
N2 C21 C26 C25 179.2(6) . . . . ?
C22 C21 C26 C30 179.5(6) . . . . ?
N2 C21 C26 C30 1.2(9) . . . . ?
C24 C25 C26 C21 2.6(10) . . . . ?
C24 C25 C26 C30 -179.4(7) . . . . ?
C23 C22 C27 C29 -74.4(8) . . . . ?
C21 C22 C27 C29 105.0(7) . . . . ?
C23 C22 C27 C28 50.6(9) . . . . ?
C21 C22 C27 C28 -130.1(6) . . . . ?
C21 C26 C30 C32 114.0(9) . . . . ?
C25 C26 C30 C32 -64.0(10) . . . . ?
C21 C26 C30 C31 -121.3(8) . . . . ?
C25 C26 C30 C31 60.8(9) . . . . ?
C44 N3 C33 C38 -0.1(8) . . . . ?
C7 N3 C33 C38 177.6(6) . . . . ?
C44 N3 C33 C34 176.7(5) . . . . ?
C7 N3 C33 C34 -5.6(8) . . . . ?
C38 C33 C34 C35 -2.7(9) . . . . ?
N3 C33 C34 C35 -179.5(6) . . . . ?
C33 C34 C35 C36 1.2(10) . . . . ?
C34 C35 C36 C37 0.8(11) . . . . ?
C35 C36 C37 C38 -1.4(12) . . . . ?
C34 C33 C38 O3 -176.3(6) . . . . ?
N3 C33 C38 O3 0.7(9) . . . . ?
C34 C33 C38 C37 2.1(9) . . . . ?
N3 C33 C38 C37 179.1(6) . . . . ?
C39 O3 C38 C33 0.1(10) . . . . ?
C39 O3 C38 C37 -178.5(7) . . . . ?
C36 C37 C38 C33 -0.2(11) . . . . ?
C36 C37 C38 O3 178.4(7) . . . . ?
C38 O3 C39 C40 179.8(7) . . . . ?
C38 O3 C39 C44 -1.4(10) . . . . ?
O3 C39 C40 C41 177.5(8) . . . . ?
C44 C39 C40 C41 -1.2(13) . . . . ?
C39 C40 C41 C42 1.7(14) . . . . ?
C40 C41 C42 C43 -1.3(14) . . . . ?
C41 C42 C43 C44 0.3(12) . . . . ?
C42 C43 C44 C39 0.2(10) . . . . ?
C42 C43 C44 N3 179.9(6) . . . . ?
C40 C39 C44 C43 0.2(10) . . . . ?
O3 C39 C44 C43 -178.4(7) . . . . ?
C40 C39 C44 N3 -179.4(7) . . . . ?
O3 C39 C44 N3 1.9(10) . . . . ?
C33 N3 C44 C43 179.3(6) . . . . ?
C7 N3 C44 C43 1.5(9) . . . . ?
C33 N3 C44 C39 -1.1(8) . . . . ?
C7 N3 C44 C39 -178.8(6) . . . . ?

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
C51 H51A Cl4 0.97 2.83 3.33(4) 112.3 .
C2 H2 O2 0.93 2.59 3.165(7) 120.5 2_655
C51 H51A Cl4 0.97 2.83 3.33(4) 112.3 .
C2 H2 O2 0.93 2.59 3.165(7) 120.5 2_655
C51 H51A Cl4 0.97 2.83 3.33(4) 112.3 .
C2 H2 O2 0.93 2.59 3.165(7) 120.5 2_655
C2 H2 O2 0.93 2.59 3.165(7) 120.5 2_655
C51 H51A Cl4 0.97 2.83 3.33(4) 112.3 .
C2 H2 O2 0.93 2.59 3.165(7) 120.5 2_655
C51 H51A Cl4 0.97 2.83 3.33(4) 112.3 .
C2 H2 O2 0.93 2.59 3.165(7) 120.5 2_655
C51 H51A Cl4 0.97 2.83 3.33(4) 112.3 .
C2 H2 O2 0.93 2.59 3.165(7) 120.5 2_655
C51 H51A Cl4 0.97 2.83 3.33(4) 112.3 .

_refine_diff_density_max         0.260
_refine_diff_density_min         -0.309
_refine_diff_density_rms         0.048

_shelxl_version_number           2014-3



####################################################################### 
# 
# 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_WDE0049_10B_A_0m
_audit_block_doi                 10.5517/ccdc.csd.cc2dcypf
_database_code_depnum_ccdc_archive 'CCDC 2216025'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/D2CC06978D 2023
loop_
_audit_author_name
_audit_author_address
'Maja Morawiak'
;Institute of Organic Chemistry Polish Academy of Science
Poland
;
_audit_update_record             
;
2022-10-28 deposited with the CCDC.	2023-12-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C48 H44 N4), C3 Cl2'
_chemical_formula_sum            'C99 H88 Cl2 N8'
_chemical_formula_weight         1460.67

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'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

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

_cell_length_a                   27.4329(5)
_cell_length_b                   14.3395(2)
_cell_length_c                   24.0718(4)
_cell_angle_alpha                90
_cell_angle_beta                 122.5130(10)
_cell_angle_gamma                90
_cell_volume                     7985.1(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4991
_cell_measurement_theta_min      3.63
_cell_measurement_theta_max      68.59

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.215
_exptl_crystal_F_000             3088
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.335
_exptl_crystal_size_mid          0.209
_exptl_crystal_size_min          0.172
_exptl_absorpt_coefficient_mu    1.143
_shelx_estimated_absorpt_T_min   0.701
_shelx_estimated_absorpt_T_max   0.828
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.7010
_exptl_absorpt_correction_T_max  0.8280
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            54101
_diffrn_reflns_av_unetI/netI     0.0420
_diffrn_reflns_av_R_equivalents  0.0777
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         3.626
_diffrn_reflns_theta_max         68.586
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             7329
_reflns_number_gt                4991
_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_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)+(0.1178P)²+18.2544P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.00010(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         7329
_refine_ls_number_parameters     513
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1135
_refine_ls_R_factor_gt           0.0830
_refine_ls_wR_factor_ref         0.2460
_refine_ls_wR_factor_gt          0.2192
_refine_ls_goodness_of_fit_ref   0.963
_refine_ls_restrained_S_all      0.963
_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 0.87015(12) 0.0820(2) 0.11767(13) 0.0518(7) Uani 1 1 d . . . . .
N2 N 1.03028(12) 0.2953(2) 0.09549(15) 0.0571(7) Uani 1 1 d . . . . .
N3 N 1.16790(12) 0.30798(19) 0.28293(14) 0.0538(7) Uani 1 1 d . . . . .
N4 N 1.19294(12) 0.1763(2) 0.21596(13) 0.0540(7) Uani 1 1 d . . . . .
C1 C 0.82422(14) 0.0386(2) 0.06249(16) 0.0489(8) Uani 1 1 d . . . . .
C2 C 0.80380(15) 0.0516(2) -0.00363(16) 0.0548(8) Uani 1 1 d . . . . .
H2 H 0.8222 0.0923 -0.0167 0.066 Uiso 1 1 calc R U . . .
C3 C 0.75558(16) 0.0024(3) -0.04924(18) 0.0597(9) Uani 1 1 d . . . . .
C4 C 0.72688(16) -0.0605(3) -0.03168(17) 0.0578(9) Uani 1 1 d . . . . .
C5 C 0.74865(15) -0.0728(3) 0.03487(17) 0.0550(9) Uani 1 1 d . . . . .
C6 C 0.79726(14) -0.0235(2) 0.08271(16) 0.0484(7) Uani 1 1 d . . . . .
C7 C 0.82863(13) -0.0181(2) 0.15402(15) 0.0470(7) Uani 1 1 d . . . . .
C8 C 0.82371(14) -0.0636(2) 0.20185(16) 0.0506(8) Uani 1 1 d . . . . .
H8 H 0.7947 -0.1076 0.1892 0.061 Uiso 1 1 calc R U . . .
C9 C 0.86185(14) -0.0440(2) 0.26854(16) 0.0494(8) Uani 1 1 d . . . . .
C10 C 0.90488(15) 0.0222(2) 0.28502(17) 0.0547(8) Uani 1 1 d . . . . .
H10 H 0.9305 0.0360 0.3293 0.066 Uiso 1 1 calc R U . . .
C11 C 0.91142(15) 0.0684(2) 0.23909(16) 0.0557(9) Uani 1 1 d . . . . .
H11 H 0.9406 0.1120 0.2519 0.067 Uiso 1 1 calc R U . . .
C12 C 0.87294(14) 0.0472(2) 0.17341(15) 0.0472(7) Uani 1 1 d . . . . .
C13 C 0.67346(19) -0.1114(3) -0.0856(2) 0.0759(12) Uani 1 1 d . . . . .
C14 C 0.6856(3) -0.1605(4) -0.1324(3) 0.1066(18) Uani 1 1 d . . . . .
H14A H 0.7118 -0.2113 -0.1100 0.160 Uiso 1 1 calc R U . . .
H14B H 0.7027 -0.1173 -0.1477 0.160 Uiso 1 1 calc R U . . .
H14C H 0.6501 -0.1841 -0.1693 0.160 Uiso 1 1 calc R U . . .
C15 C 0.6263(2) -0.0380(5) -0.1269(3) 0.119(2) Uani 1 1 d . . . . .
H15A H 0.5928 -0.0684 -0.1623 0.178 Uiso 1 1 calc R U . . .
H15B H 0.6407 0.0062 -0.1446 0.178 Uiso 1 1 calc R U . . .
H15C H 0.6162 -0.0062 -0.0994 0.178 Uiso 1 1 calc R U . . .
C16 C 0.6482(3) -0.1751(6) -0.0594(3) 0.164(4) Uani 1 1 d . . . . .
H16A H 0.6757 -0.2229 -0.0335 0.246 Uiso 1 1 calc R U . . .
H16B H 0.6139 -0.2031 -0.0953 0.246 Uiso 1 1 calc R U . . .
H16C H 0.6387 -0.1406 -0.0323 0.246 Uiso 1 1 calc R U . . .
C17 C 0.85645(17) -0.0960(2) 0.32058(17) 0.0584(9) Uani 1 1 d . . . . .
C18 C 0.79660(19) -0.0803(4) 0.3089(2) 0.0836(13) Uani 1 1 d . . . . .
H18A H 0.7903 -0.0147 0.3101 0.125 Uiso 1 1 calc R U . . .
H18B H 0.7942 -0.1114 0.3427 0.125 Uiso 1 1 calc R U . . .
H18C H 0.7677 -0.1050 0.2667 0.125 Uiso 1 1 calc R U . . .
C19 C 0.9010(2) -0.0615(3) 0.39093(19) 0.0791(12) Uani 1 1 d . . . . .
H19A H 0.9393 -0.0710 0.4003 0.119 Uiso 1 1 calc R U . . .
H19B H 0.8963 -0.0957 0.4221 0.119 Uiso 1 1 calc R U . . .
H19C H 0.8950 0.0037 0.3942 0.119 Uiso 1 1 calc R U . . .
C20 C 0.8672(3) -0.1996(3) 0.3176(2) 0.0920(15) Uani 1 1 d . . . . .
H20A H 0.8384 -0.2239 0.2752 0.138 Uiso 1 1 calc R U . . .
H20B H 0.8653 -0.2321 0.3512 0.138 Uiso 1 1 calc R U . . .
H20C H 0.9048 -0.2081 0.3245 0.138 Uiso 1 1 calc R U . . .
C21 C 0.91325(14) 0.1353(2) 0.11633(16) 0.0485(8) Uani 1 1 d . . . . .
C22 C 0.93835(14) 0.0999(2) 0.08431(16) 0.0507(8) Uani 1 1 d . . . . .
H22 H 0.9289 0.0399 0.0669 0.061 Uiso 1 1 calc R U . . .
C23 C 0.97719(14) 0.1518(2) 0.07774(16) 0.0504(8) Uani 1 1 d . . . . .
H23 H 0.9931 0.1272 0.0552 0.060 Uiso 1 1 calc R U . . .
C24 C 0.99276(13) 0.2413(2) 0.10478(15) 0.0467(7) Uani 1 1 d . . . . .
C25 C 0.96918(14) 0.2748(2) 0.13946(17) 0.0528(8) Uani 1 1 d . . . . .
H25 H 0.9803 0.3331 0.1594 0.063 Uiso 1 1 calc R U . . .
C26 C 0.92939(15) 0.2226(2) 0.14475(17) 0.0521(8) Uani 1 1 d . . . . .
C27 C 1.04973(15) 0.3840(2) 0.12617(18) 0.0565(9) Uani 1 1 d . . . . .
C28 C 1.01568(18) 0.4615(3) 0.0973(2) 0.0757(12) Uani 1 1 d . . . . .
H28 H 0.9805 0.4561 0.0574 0.091 Uiso 1 1 calc R U . . .
C29 C 1.0339(2) 0.5479(3) 0.1279(3) 0.0840(13) Uani 1 1 d . . . . .
H29 H 1.0108 0.6004 0.1089 0.101 Uiso 1 1 calc R U . . .
C30 C 1.0863(2) 0.5551(3) 0.1867(2) 0.0784(12) Uani 1 1 d . . . . .
H30 H 1.0986 0.6128 0.2073 0.094 Uiso 1 1 calc R U . . .
C31 C 1.12059(18) 0.4778(3) 0.2152(2) 0.0654(10) Uani 1 1 d . . . . .
H31 H 1.1560 0.4838 0.2548 0.078 Uiso 1 1 calc R U . . .
C32 C 1.10270(15) 0.3904(2) 0.18511(17) 0.0528(8) Uani 1 1 d . . . . .
C33 C 1.14015(14) 0.3083(2) 0.21758(17) 0.0511(8) Uani 1 1 d . . . . .
C34 C 1.15116(14) 0.2382(2) 0.18335(16) 0.0499(8) Uani 1 1 d . . . . .
C35 C 1.11948(15) 0.2288(2) 0.11077(17) 0.0526(8) Uani 1 1 d . . . . .
C36 C 1.14637(18) 0.1856(3) 0.08209(19) 0.0638(10) Uani 1 1 d . . . . .
H36 H 1.1850 0.1682 0.1086 0.077 Uiso 1 1 calc R U . . .
C37 C 1.1169(2) 0.1680(3) 0.0152(2) 0.0748(12) Uani 1 1 d . . . . .
H37 H 1.1354 0.1380 -0.0027 0.090 Uiso 1 1 calc R U . . .
C38 C 1.0600(2) 0.1951(4) -0.0249(2) 0.0817(13) Uani 1 1 d . . . . .
H38 H 1.0400 0.1836 -0.0699 0.098 Uiso 1 1 calc R U . . .
C39 C 1.03316(18) 0.2393(3) 0.00223(19) 0.0727(12) Uani 1 1 d . . . . .
H39 H 0.9951 0.2588 -0.0250 0.087 Uiso 1 1 calc R U . . .
C40 C 1.06158(15) 0.2551(3) 0.06908(17) 0.0571(9) Uani 1 1 d . . . . .
C41 C 1.20821(15) 0.2419(2) 0.31592(16) 0.0523(8) Uani 1 1 d . . . . .
C42 C 1.23958(17) 0.2392(3) 0.38524(17) 0.0602(9) Uani 1 1 d . . . . .
H42 H 1.2295 0.2797 0.4076 0.072 Uiso 1 1 calc R U . . .
C43 C 1.28450(16) 0.1785(3) 0.42065(18) 0.0627(10) Uani 1 1 d . . . . .
C44 C 1.29985(16) 0.1152(3) 0.38634(19) 0.0649(10) Uani 1 1 d . . . . .
C45 C 1.26912(16) 0.1155(3) 0.31952(19) 0.0644(10) Uani 1 1 d . . . . .
H45 H 1.2789 0.0737 0.2975 0.077 Uiso 1 1 calc R U . . .
C46 C 1.22290(15) 0.1775(2) 0.28272(16) 0.0525(8) Uani 1 1 d . . . . .
C47 C 1.3178(2) 0.1781(4) 0.49447(19) 0.0861(14) Uani 1 1 d . . . . .
H47A H 1.3040 0.2273 0.5096 0.129 Uiso 1 1 calc R U . . .
H47B H 1.3581 0.1875 0.5115 0.129 Uiso 1 1 calc R U . . .
H47C H 1.3126 0.1193 0.5096 0.129 Uiso 1 1 calc R U . . .
C48 C 1.3506(2) 0.0497(4) 0.4246(2) 0.0977(16) Uani 1 1 d . . . . .
H48A H 1.3513 0.0059 0.3949 0.147 Uiso 1 1 calc R U . . .
H48B H 1.3467 0.0166 0.4567 0.147 Uiso 1 1 calc R U . . .
H48C H 1.3859 0.0849 0.4465 0.147 Uiso 1 1 calc R U . . .
H3 H 0.7423(17) 0.010(3) -0.095(2) 0.072(11) Uiso 1 1 d . . . . .
H5 H 0.7299(15) -0.115(2) 0.0492(16) 0.054(9) Uiso 1 1 d . . . . .
H26 H 0.9125(15) 0.245(2) 0.1665(17) 0.059(10) Uiso 1 1 d . . . . .
C52 C 0.0395(3) 0.8781(3) 0.3253(2) 0.0944(16) Uani 1 1 d . . . . .
C51 C 0.0000 0.8713(8) 0.2500 0.226(8) Uani 1 2 d S T P . .
Cl1 Cl -0.0027(4) 0.7598(7) 0.2146(3) 0.517(6) 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 1.394(4) . ?
N1 C1 1.393(4) . ?
N1 C21 1.423(4) . ?
N2 C24 1.399(4) . ?
N2 C27 1.423(4) . ?
N2 C40 1.435(5) . ?
N3 C33 1.329(4) . ?
N3 C41 1.345(4) . ?
N4 C34 1.323(4) . ?
N4 C46 1.356(4) . ?
C1 C2 1.387(4) . ?
C1 C6 1.401(4) . ?
C2 C3 1.375(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.403(5) . ?
C3 H3 0.97(4) . ?
C4 C5 1.388(5) . ?
C4 C13 1.523(5) . ?
C5 C6 1.397(4) . ?
C5 H5 0.97(4) . ?
C6 C7 1.451(4) . ?
C7 C8 1.392(4) . ?
C7 C12 1.402(4) . ?
C8 C9 1.395(4) . ?
C8 H8 0.9300 . ?
C9 C10 1.396(5) . ?
C9 C17 1.532(4) . ?
C10 C11 1.380(5) . ?
C10 H10 0.9300 . ?
C11 C12 1.383(4) . ?
C11 H11 0.9300 . ?
C13 C16 1.476(6) . ?
C13 C14 1.511(7) . ?
C13 C15 1.545(7) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 C20 1.524(5) . ?
C17 C18 1.526(6) . ?
C17 C19 1.543(5) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 C22 1.377(5) . ?
C21 C26 1.381(5) . ?
C22 C23 1.377(4) . ?
C22 H22 0.9300 . ?
C23 C24 1.398(5) . ?
C23 H23 0.9300 . ?
C24 C25 1.388(5) . ?
C25 C26 1.385(5) . ?
C25 H25 0.9300 . ?
C26 H26 0.93(4) . ?
C27 C28 1.376(5) . ?
C27 C32 1.384(5) . ?
C28 C29 1.389(6) . ?
C28 H28 0.9300 . ?
C29 C30 1.375(6) . ?
C29 H29 0.9300 . ?
C30 C31 1.375(6) . ?
C30 H30 0.9300 . ?
C31 C32 1.398(5) . ?
C31 H31 0.9300 . ?
C32 C33 1.479(5) . ?
C33 C34 1.431(5) . ?
C34 C35 1.481(5) . ?
C35 C40 1.400(5) . ?
C35 C36 1.397(5) . ?
C36 C37 1.382(5) . ?
C36 H36 0.9300 . ?
C37 C38 1.377(6) . ?
C37 H37 0.9300 . ?
C38 C39 1.373(6) . ?
C38 H38 0.9300 . ?
C39 C40 1.379(5) . ?
C39 H39 0.9300 . ?
C41 C46 1.415(5) . ?
C41 C42 1.408(5) . ?
C42 C43 1.368(5) . ?
C42 H42 0.9300 . ?
C43 C44 1.434(6) . ?
C43 C47 1.499(5) . ?
C44 C45 1.357(5) . ?
C44 C48 1.513(6) . ?
C45 C46 1.405(5) . ?
C45 H45 0.9300 . ?
C47 H47A 0.9600 . ?
C47 H47B 0.9600 . ?
C47 H47C 0.9600 . ?
C48 H48A 0.9600 . ?
C48 H48B 0.9600 . ?
C48 H48C 0.9600 . ?
C52 C51 1.535(5) . ?
C52 Cl1 1.943(11) 2 ?
C51 C52 1.535(5) 2 ?
C51 Cl1 1.794(12) . ?
C51 Cl1 1.794(12) 2 ?
Cl1 Cl1 1.629(12) 2 ?
Cl1 C52 1.943(11) 2 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C12 N1 C1 108.2(2) . . ?
C12 N1 C21 126.7(3) . . ?
C1 N1 C21 123.7(3) . . ?
C24 N2 C27 121.0(3) . . ?
C24 N2 C40 121.1(3) . . ?
C27 N2 C40 116.2(3) . . ?
C33 N3 C41 117.9(3) . . ?
C34 N4 C46 118.4(3) . . ?
C2 C1 N1 129.4(3) . . ?
C2 C1 C6 121.4(3) . . ?
N1 C1 C6 109.2(3) . . ?
C3 C2 C1 118.0(3) . . ?
C3 C2 H2 121.0 . . ?
C1 C2 H2 121.0 . . ?
C2 C3 C4 122.9(3) . . ?
C2 C3 H3 117(2) . . ?
C4 C3 H3 120(2) . . ?
C5 C4 C3 117.8(3) . . ?
C5 C4 C13 122.9(3) . . ?
C3 C4 C13 119.3(3) . . ?
C4 C5 C6 121.0(3) . . ?
C4 C5 H5 121(2) . . ?
C6 C5 H5 118(2) . . ?
C5 C6 C1 118.9(3) . . ?
C5 C6 C7 134.3(3) . . ?
C1 C6 C7 106.8(3) . . ?
C8 C7 C12 119.4(3) . . ?
C8 C7 C6 134.0(3) . . ?
C12 C7 C6 106.6(3) . . ?
C7 C8 C9 120.7(3) . . ?
C7 C8 H8 119.6 . . ?
C9 C8 H8 119.6 . . ?
C10 C9 C8 117.5(3) . . ?
C10 C9 C17 122.5(3) . . ?
C8 C9 C17 120.0(3) . . ?
C11 C10 C9 123.5(3) . . ?
C11 C10 H10 118.2 . . ?
C9 C10 H10 118.2 . . ?
C10 C11 C12 117.6(3) . . ?
C10 C11 H11 121.2 . . ?
C12 C11 H11 121.2 . . ?
C11 C12 C7 121.3(3) . . ?
C11 C12 N1 129.5(3) . . ?
C7 C12 N1 109.2(3) . . ?
C16 C13 C14 111.9(5) . . ?
C16 C13 C4 112.9(3) . . ?
C14 C13 C4 111.2(4) . . ?
C16 C13 C15 105.9(5) . . ?
C14 C13 C15 106.4(4) . . ?
C4 C13 C15 108.1(4) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C20 C17 C9 109.2(3) . . ?
C20 C17 C18 110.6(4) . . ?
C9 C17 C18 110.2(3) . . ?
C20 C17 C19 107.8(3) . . ?
C9 C17 C19 111.9(3) . . ?
C18 C17 C19 107.0(3) . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C17 C19 H19A 109.5 . . ?
C17 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C17 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C17 C20 H20A 109.5 . . ?
C17 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C17 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C22 C21 C26 119.2(3) . . ?
C22 C21 N1 119.1(3) . . ?
C26 C21 N1 121.7(3) . . ?
C23 C22 C21 121.0(3) . . ?
C23 C22 H22 119.5 . . ?
C21 C22 H22 119.5 . . ?
C22 C23 C24 120.3(3) . . ?
C22 C23 H23 119.9 . . ?
C24 C23 H23 119.9 . . ?
C25 C24 N2 121.7(3) . . ?
C25 C24 C23 118.3(3) . . ?
N2 C24 C23 120.0(3) . . ?
C24 C25 C26 120.9(3) . . ?
C24 C25 H25 119.6 . . ?
C26 C25 H25 119.6 . . ?
C21 C26 C25 120.2(3) . . ?
C21 C26 H26 118(2) . . ?
C25 C26 H26 122(2) . . ?
C28 C27 C32 121.1(4) . . ?
C28 C27 N2 119.8(3) . . ?
C32 C27 N2 119.0(3) . . ?
C27 C28 C29 120.0(4) . . ?
C27 C28 H28 120.0 . . ?
C29 C28 H28 120.0 . . ?
C30 C29 C28 119.4(4) . . ?
C30 C29 H29 120.3 . . ?
C28 C29 H29 120.3 . . ?
C29 C30 C31 120.7(4) . . ?
C29 C30 H30 119.7 . . ?
C31 C30 H30 119.7 . . ?
C30 C31 C32 120.6(4) . . ?
C30 C31 H31 119.7 . . ?
C32 C31 H31 119.7 . . ?
C27 C32 C31 118.2(3) . . ?
C27 C32 C33 122.5(3) . . ?
C31 C32 C33 119.3(3) . . ?
N3 C33 C34 121.0(3) . . ?
N3 C33 C32 114.9(3) . . ?
C34 C33 C32 123.8(3) . . ?
N4 C34 C33 120.9(3) . . ?
N4 C34 C35 114.2(3) . . ?
C33 C34 C35 124.9(3) . . ?
C40 C35 C36 117.5(3) . . ?
C40 C35 C34 122.8(3) . . ?
C36 C35 C34 119.5(3) . . ?
C37 C36 C35 121.5(4) . . ?
C37 C36 H36 119.2 . . ?
C35 C36 H36 119.2 . . ?
C38 C37 C36 119.9(4) . . ?
C38 C37 H37 120.1 . . ?
C36 C37 H37 120.1 . . ?
C37 C38 C39 119.5(4) . . ?
C37 C38 H38 120.3 . . ?
C39 C38 H38 120.3 . . ?
C38 C39 C40 121.3(4) . . ?
C38 C39 H39 119.3 . . ?
C40 C39 H39 119.3 . . ?
C35 C40 C39 120.3(4) . . ?
C35 C40 N2 120.6(3) . . ?
C39 C40 N2 119.1(3) . . ?
N3 C41 C46 121.4(3) . . ?
N3 C41 C42 120.3(3) . . ?
C46 C41 C42 118.2(3) . . ?
C43 C42 C41 121.9(4) . . ?
C43 C42 H42 119.1 . . ?
C41 C42 H42 119.1 . . ?
C42 C43 C44 119.2(3) . . ?
C42 C43 C47 120.8(4) . . ?
C44 C43 C47 120.0(4) . . ?
C45 C44 C43 119.5(4) . . ?
C45 C44 C48 120.4(4) . . ?
C43 C44 C48 120.1(4) . . ?
C44 C45 C46 121.7(4) . . ?
C44 C45 H45 119.2 . . ?
C46 C45 H45 119.2 . . ?
N4 C46 C45 120.4(3) . . ?
N4 C46 C41 120.1(3) . . ?
C45 C46 C41 119.4(3) . . ?
C43 C47 H47A 109.5 . . ?
C43 C47 H47B 109.5 . . ?
H47A C47 H47B 109.5 . . ?
C43 C47 H47C 109.5 . . ?
H47A C47 H47C 109.5 . . ?
H47B C47 H47C 109.5 . . ?
C44 C48 H48A 109.5 . . ?
C44 C48 H48B 109.5 . . ?
H48A C48 H48B 109.5 . . ?
C44 C48 H48C 109.5 . . ?
H48A C48 H48C 109.5 . . ?
H48B C48 H48C 109.5 . . ?
C51 C52 Cl1 60.8(4) . 2 ?
C52 C51 C52 172.7(9) . 2 ?
C52 C51 Cl1 116.1(6) . . ?
C52 C51 Cl1 70.9(4) 2 . ?
C52 C51 Cl1 70.9(4) . 2 ?
C52 C51 Cl1 116.1(6) 2 2 ?
Cl1 C51 Cl1 54.0(5) . 2 ?
Cl1 Cl1 C51 63.0(3) 2 . ?
Cl1 Cl1 C52 104.3(5) 2 2 ?
C51 Cl1 C52 48.3(3) . 2 ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C12 N1 C1 C2 178.5(4) . . . . ?
C21 N1 C1 C2 -14.3(6) . . . . ?
C12 N1 C1 C6 0.4(4) . . . . ?
C21 N1 C1 C6 167.6(3) . . . . ?
N1 C1 C2 C3 -177.1(4) . . . . ?
C6 C1 C2 C3 0.8(5) . . . . ?
C1 C2 C3 C4 -0.7(6) . . . . ?
C2 C3 C4 C5 0.0(6) . . . . ?
C2 C3 C4 C13 179.5(4) . . . . ?
C3 C4 C5 C6 0.5(6) . . . . ?
C13 C4 C5 C6 -178.9(4) . . . . ?
C4 C5 C6 C1 -0.4(6) . . . . ?
C4 C5 C6 C7 177.5(4) . . . . ?
C2 C1 C6 C5 -0.2(5) . . . . ?
N1 C1 C6 C5 178.0(3) . . . . ?
C2 C1 C6 C7 -178.7(3) . . . . ?
N1 C1 C6 C7 -0.4(4) . . . . ?
C5 C6 C7 C8 3.7(7) . . . . ?
C1 C6 C7 C8 -178.2(4) . . . . ?
C5 C6 C7 C12 -177.9(4) . . . . ?
C1 C6 C7 C12 0.2(4) . . . . ?
C12 C7 C8 C9 0.8(5) . . . . ?
C6 C7 C8 C9 179.0(4) . . . . ?
C7 C8 C9 C10 -0.3(5) . . . . ?
C7 C8 C9 C17 -178.9(3) . . . . ?
C8 C9 C10 C11 -0.1(5) . . . . ?
C17 C9 C10 C11 178.4(3) . . . . ?
C9 C10 C11 C12 0.1(6) . . . . ?
C10 C11 C12 C7 0.4(5) . . . . ?
C10 C11 C12 N1 -179.0(3) . . . . ?
C8 C7 C12 C11 -0.8(5) . . . . ?
C6 C7 C12 C11 -179.5(3) . . . . ?
C8 C7 C12 N1 178.7(3) . . . . ?
C6 C7 C12 N1 0.0(4) . . . . ?
C1 N1 C12 C11 179.2(4) . . . . ?
C21 N1 C12 C11 12.6(6) . . . . ?
C1 N1 C12 C7 -0.3(4) . . . . ?
C21 N1 C12 C7 -166.9(3) . . . . ?
C5 C4 C13 C16 -0.7(7) . . . . ?
C3 C4 C13 C16 179.9(6) . . . . ?
C5 C4 C13 C14 -127.4(5) . . . . ?
C3 C4 C13 C14 53.2(6) . . . . ?
C5 C4 C13 C15 116.2(5) . . . . ?
C3 C4 C13 C15 -63.3(5) . . . . ?
C10 C9 C17 C20 -115.5(4) . . . . ?
C8 C9 C17 C20 63.0(5) . . . . ?
C10 C9 C17 C18 122.7(4) . . . . ?
C8 C9 C17 C18 -58.8(5) . . . . ?
C10 C9 C17 C19 3.8(5) . . . . ?
C8 C9 C17 C19 -177.7(3) . . . . ?
C12 N1 C21 C22 118.2(4) . . . . ?
C1 N1 C21 C22 -46.5(5) . . . . ?
C12 N1 C21 C26 -63.6(5) . . . . ?
C1 N1 C21 C26 131.7(4) . . . . ?
C26 C21 C22 C23 -2.9(5) . . . . ?
N1 C21 C22 C23 175.3(3) . . . . ?
C21 C22 C23 C24 1.3(5) . . . . ?
C27 N2 C24 C25 5.5(5) . . . . ?
C40 N2 C24 C25 169.8(3) . . . . ?
C27 N2 C24 C23 -175.8(3) . . . . ?
C40 N2 C24 C23 -11.4(5) . . . . ?
C22 C23 C24 C25 1.6(5) . . . . ?
C22 C23 C24 N2 -177.2(3) . . . . ?
N2 C24 C25 C26 176.0(3) . . . . ?
C23 C24 C25 C26 -2.7(5) . . . . ?
C22 C21 C26 C25 1.8(5) . . . . ?
N1 C21 C26 C25 -176.5(3) . . . . ?
C24 C25 C26 C21 1.1(5) . . . . ?
C24 N2 C27 C28 -83.3(4) . . . . ?
C40 N2 C27 C28 111.6(4) . . . . ?
C24 N2 C27 C32 96.2(4) . . . . ?
C40 N2 C27 C32 -68.9(4) . . . . ?
C32 C27 C28 C29 -1.0(6) . . . . ?
N2 C27 C28 C29 178.4(4) . . . . ?
C27 C28 C29 C30 0.7(7) . . . . ?
C28 C29 C30 C31 0.0(7) . . . . ?
C29 C30 C31 C32 -0.3(7) . . . . ?
C28 C27 C32 C31 0.7(5) . . . . ?
N2 C27 C32 C31 -178.8(3) . . . . ?
C28 C27 C32 C33 179.6(3) . . . . ?
N2 C27 C32 C33 0.1(5) . . . . ?
C30 C31 C32 C27 0.0(6) . . . . ?
C30 C31 C32 C33 -178.9(4) . . . . ?
C41 N3 C33 C34 2.6(5) . . . . ?
C41 N3 C33 C32 -171.6(3) . . . . ?
C27 C32 C33 N3 -142.2(3) . . . . ?
C31 C32 C33 N3 36.8(4) . . . . ?
C27 C32 C33 C34 43.9(5) . . . . ?
C31 C32 C33 C34 -137.2(4) . . . . ?
C46 N4 C34 C33 3.8(5) . . . . ?
C46 N4 C34 C35 -177.6(3) . . . . ?
N3 C33 C34 N4 -6.3(5) . . . . ?
C32 C33 C34 N4 167.3(3) . . . . ?
N3 C33 C34 C35 175.3(3) . . . . ?
C32 C33 C34 C35 -11.1(5) . . . . ?
N4 C34 C35 C40 151.1(3) . . . . ?
C33 C34 C35 C40 -30.4(5) . . . . ?
N4 C34 C35 C36 -23.9(4) . . . . ?
C33 C34 C35 C36 154.7(3) . . . . ?
C40 C35 C36 C37 -0.9(5) . . . . ?
C34 C35 C36 C37 174.3(3) . . . . ?
C35 C36 C37 C38 1.4(6) . . . . ?
C36 C37 C38 C39 -0.1(7) . . . . ?
C37 C38 C39 C40 -1.5(7) . . . . ?
C36 C35 C40 C39 -0.7(5) . . . . ?
C34 C35 C40 C39 -175.8(3) . . . . ?
C36 C35 C40 N2 176.6(3) . . . . ?
C34 C35 C40 N2 1.5(5) . . . . ?
C38 C39 C40 C35 2.0(6) . . . . ?
C38 C39 C40 N2 -175.4(4) . . . . ?
C24 N2 C40 C35 -99.6(4) . . . . ?
C27 N2 C40 C35 65.5(4) . . . . ?
C24 N2 C40 C39 77.8(4) . . . . ?
C27 N2 C40 C39 -117.1(4) . . . . ?
C33 N3 C41 C46 3.1(5) . . . . ?
C33 N3 C41 C42 179.0(3) . . . . ?
N3 C41 C42 C43 -173.9(3) . . . . ?
C46 C41 C42 C43 2.1(5) . . . . ?
C41 C42 C43 C44 -0.6(5) . . . . ?
C41 C42 C43 C47 179.0(4) . . . . ?
C42 C43 C44 C45 -1.0(6) . . . . ?
C47 C43 C44 C45 179.4(4) . . . . ?
C42 C43 C44 C48 178.1(4) . . . . ?
C47 C43 C44 C48 -1.5(6) . . . . ?
C43 C44 C45 C46 1.0(6) . . . . ?
C48 C44 C45 C46 -178.1(4) . . . . ?
C34 N4 C46 C45 -177.5(3) . . . . ?
C34 N4 C46 C41 1.8(5) . . . . ?
C44 C45 C46 N4 179.9(3) . . . . ?
C44 C45 C46 C41 0.6(5) . . . . ?
N3 C41 C46 N4 -5.5(5) . . . . ?
C42 C41 C46 N4 178.5(3) . . . . ?
N3 C41 C46 C45 173.8(3) . . . . ?
C42 C41 C46 C45 -2.1(5) . . . . ?
Cl1 C52 C51 Cl1 -30.5(7) 2 . . . ?
C52 C51 Cl1 Cl1 36.3(8) . . . 2 ?
C52 C51 Cl1 Cl1 -145.7(7) 2 . . 2 ?
C52 C51 Cl1 C52 -177.9(3) . . . 2 ?
Cl1 C51 Cl1 C52 145.7(7) 2 . . 2 ?

_refine_diff_density_max         0.658
_refine_diff_density_min         -0.942
_refine_diff_density_rms         0.061

_shelxl_version_number           2014-3



