# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_1_a
_database_code_depnum_ccdc_archive 'CCDC 1821566'
_audit_update_record             
;
2018-02-02 deposited with the CCDC.
2018-05-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C37 H22 N4 O'
_chemical_formula_weight         538.58

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

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

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

_cell_length_a                   19.964(2)
_cell_length_b                   13.6664(14)
_cell_length_c                   20.645(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     5632.7(10)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1857
_cell_measurement_theta_min      2.22
_cell_measurement_theta_max      18.14

_exptl_crystal_description       Block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.270
_exptl_crystal_F_000             2240
_exptl_transmission_factor_min   0.864
_exptl_transmission_factor_max   0.864
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    0.078
_shelx_estimated_absorpt_T_min   0.983
_shelx_estimated_absorpt_T_max   0.986
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  CCD
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            34723
_diffrn_reflns_av_unetI/netI     0.0583
_diffrn_reflns_av_R_equivalents  0.0910
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         1.973
_diffrn_reflns_theta_max         25.055
_diffrn_reflns_theta_full        25.055
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4997
_reflns_number_gt                2750
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0706P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4997
_refine_ls_number_parameters     379
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1096
_refine_ls_R_factor_gt           0.0524
_refine_ls_wR_factor_ref         0.1496
_refine_ls_wR_factor_gt          0.1186
_refine_ls_goodness_of_fit_ref   0.978
_refine_ls_restrained_S_all      0.978
_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
C1 C 0.59960(15) 0.4888(2) 0.40730(14) 0.0767(9) Uani 1 1 d . . . . .
H1 H 0.6135 0.4400 0.3789 0.092 Uiso 1 1 calc R U . . .
C2 C 0.62065(18) 0.4876(3) 0.47113(16) 0.0992(12) Uani 1 1 d . . . . .
H2 H 0.6479 0.4371 0.4859 0.119 Uiso 1 1 calc R U . . .
C3 C 0.60148(17) 0.5605(3) 0.51264(15) 0.0864(10) Uani 1 1 d . . . . .
H3 H 0.6161 0.5595 0.5554 0.104 Uiso 1 1 calc R U . . .
C4 C 0.56132(17) 0.6340(2) 0.49198(14) 0.0770(9) Uani 1 1 d . . . . .
H4 H 0.5486 0.6835 0.5204 0.092 Uiso 1 1 calc R U . . .
C5 C 0.53938(14) 0.6353(2) 0.42855(13) 0.0635(8) Uani 1 1 d . . . . .
H5 H 0.5117 0.6857 0.4144 0.076 Uiso 1 1 calc R U . . .
C6 C 0.55805(12) 0.5624(2) 0.38583(12) 0.0506(7) Uani 1 1 d . . . . .
C7 C 0.53552(11) 0.56389(18) 0.31754(11) 0.0459(6) Uani 1 1 d . . . . .
C8 C 0.47171(11) 0.59649(18) 0.29869(11) 0.0448(6) Uani 1 1 d . . . . .
C9 C 0.45648(11) 0.60490(17) 0.23293(11) 0.0425(6) Uani 1 1 d . . . . .
C10 C 0.50413(11) 0.57443(18) 0.18840(11) 0.0426(6) Uani 1 1 d . . . . .
C11 C 0.56409(11) 0.53165(18) 0.21063(11) 0.0437(6) Uani 1 1 d . . . . .
C12 C 0.61347(11) 0.48492(18) 0.16709(12) 0.0460(6) Uani 1 1 d . . . . .
C13 C 0.59370(14) 0.4258(2) 0.11622(13) 0.0601(7) Uani 1 1 d . . . . .
H13 H 0.5484 0.4164 0.1080 0.072 Uiso 1 1 calc R U . . .
C14 C 0.64107(16) 0.3806(2) 0.07741(15) 0.0752(9) Uani 1 1 d . . . . .
H14 H 0.6275 0.3404 0.0435 0.090 Uiso 1 1 calc R U . . .
C15 C 0.70768(17) 0.3951(2) 0.08909(17) 0.0797(10) Uani 1 1 d . . . . .
H15 H 0.7394 0.3653 0.0626 0.096 Uiso 1 1 calc R U . . .
C16 C 0.72828(13) 0.4531(2) 0.13944(16) 0.0722(9) Uani 1 1 d . . . . .
H16 H 0.7737 0.4627 0.1470 0.087 Uiso 1 1 calc R U . . .
C17 C 0.68136(12) 0.4970(2) 0.17885(13) 0.0577(7) Uani 1 1 d . . . . .
H17 H 0.6954 0.5352 0.2136 0.069 Uiso 1 1 calc R U . . .
C18 C 0.41920(13) 0.6152(2) 0.34496(13) 0.0554(7) Uani 1 1 d . . . . .
C19 C 0.49269(12) 0.5927(2) 0.12100(13) 0.0526(7) Uani 1 1 d . . . . .
C20 C 0.39057(11) 0.64543(19) 0.21285(11) 0.0444(6) Uani 1 1 d . . . . .
C21 C 0.37387(12) 0.7404(2) 0.22834(13) 0.0582(7) Uani 1 1 d . . . . .
H21 H 0.4050 0.7798 0.2493 0.070 Uiso 1 1 calc R U . . .
C22 C 0.31206(13) 0.7776(2) 0.21327(12) 0.0584(7) Uani 1 1 d . . . . .
H22 H 0.3018 0.8423 0.2230 0.070 Uiso 1 1 calc R U . . .
C23 C 0.26511(12) 0.7183(2) 0.18358(11) 0.0493(7) Uani 1 1 d . . . . .
C24 C 0.28077(13) 0.6243(2) 0.16809(13) 0.0601(8) Uani 1 1 d . . . . .
H24 H 0.2491 0.5844 0.1482 0.072 Uiso 1 1 calc R U . . .
C25 C 0.34389(12) 0.5881(2) 0.18194(12) 0.0580(7) Uani 1 1 d . . . . .
H25 H 0.3548 0.5243 0.1702 0.070 Uiso 1 1 calc R U . . .
C26 C 0.15611(12) 0.77856(18) 0.22085(11) 0.0452(6) Uani 1 1 d . . . . .
C27 C 0.16949(12) 0.7562(2) 0.28500(12) 0.0538(7) Uani 1 1 d . . . . .
H27 H 0.2101 0.7272 0.2959 0.065 Uiso 1 1 calc R U . . .
C28 C 0.12335(14) 0.7766(2) 0.33290(13) 0.0616(8) Uani 1 1 d . . . . .
H28 H 0.1330 0.7605 0.3757 0.074 Uiso 1 1 calc R U . . .
C29 C 0.06356(14) 0.8200(2) 0.31830(13) 0.0626(8) Uani 1 1 d . . . . .
H29 H 0.0326 0.8338 0.3507 0.075 Uiso 1 1 calc R U . . .
C30 C 0.05009(13) 0.84303(19) 0.25466(13) 0.0560(7) Uani 1 1 d . . . . .
H30 H 0.0096 0.8726 0.2441 0.067 Uiso 1 1 calc R U . . .
C31 C 0.09521(12) 0.82322(17) 0.20684(12) 0.0459(6) Uani 1 1 d . . . . .
C32 C 0.12701(12) 0.84236(18) 0.09700(12) 0.0481(6) Uani 1 1 d . . . . .
C33 C 0.18788(12) 0.79696(18) 0.10859(11) 0.0480(6) Uani 1 1 d . . . . .
C34 C 0.23382(13) 0.7933(2) 0.05855(12) 0.0606(8) Uani 1 1 d . . . . .
H34 H 0.2751 0.7633 0.0652 0.073 Uiso 1 1 calc R U . . .
C35 C 0.21933(15) 0.8337(2) -0.00117(13) 0.0657(8) Uani 1 1 d . . . . .
H35 H 0.2506 0.8308 -0.0345 0.079 Uiso 1 1 calc R U . . .
C36 C 0.15867(16) 0.8779(2) -0.01115(14) 0.0691(8) Uani 1 1 d . . . . .
H36 H 0.1486 0.9044 -0.0515 0.083 Uiso 1 1 calc R U . . .
C37 C 0.11257(14) 0.8832(2) 0.03814(13) 0.0611(8) Uani 1 1 d . . . . .
H37 H 0.0717 0.9144 0.0315 0.073 Uiso 1 1 calc R U . . .
N1 N 0.57913(9) 0.53004(15) 0.27386(9) 0.0490(5) Uani 1 1 d . . . . .
N2 N 0.37535(13) 0.6281(2) 0.37911(12) 0.0808(8) Uani 1 1 d . . . . .
N3 N 0.48231(12) 0.6114(2) 0.06814(12) 0.0770(8) Uani 1 1 d . . . . .
N4 N 0.19947(10) 0.75562(17) 0.17000(9) 0.0584(6) Uani 1 1 d . . . . .
O1 O 0.07765(8) 0.84779(15) 0.14414(8) 0.0659(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
C1 C6 1.377(4) . ?
C1 C2 1.383(4) . ?
C1 H1 0.9300 . ?
C2 C3 1.369(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.355(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.381(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.382(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.480(3) . ?
C7 N1 1.336(3) . ?
C7 C8 1.404(3) . ?
C8 C9 1.396(3) . ?
C8 C18 1.441(3) . ?
C9 C10 1.387(3) . ?
C9 C20 1.487(3) . ?
C10 C11 1.409(3) . ?
C10 C19 1.432(3) . ?
C11 N1 1.340(3) . ?
C11 C12 1.479(3) . ?
C12 C13 1.382(3) . ?
C12 C17 1.387(3) . ?
C13 C14 1.385(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.366(4) . ?
C14 H14 0.9300 . ?
C15 C16 1.371(4) . ?
C15 H15 0.9300 . ?
C16 C17 1.378(3) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C18 N2 1.138(3) . ?
C19 N3 1.140(3) . ?
C20 C25 1.375(3) . ?
C20 C21 1.377(3) . ?
C21 C22 1.370(3) . ?
C21 H21 0.9300 . ?
C22 C23 1.382(3) . ?
C22 H22 0.9300 . ?
C23 C24 1.361(3) . ?
C23 N4 1.434(3) . ?
C24 C25 1.384(3) . ?
C24 H24 0.9300 . ?
C25 H25 0.9300 . ?
C26 C27 1.385(3) . ?
C26 C31 1.391(3) . ?
C26 N4 1.396(3) . ?
C27 C28 1.380(3) . ?
C27 H27 0.9300 . ?
C28 C29 1.367(4) . ?
C28 H28 0.9300 . ?
C29 C30 1.378(3) . ?
C29 H29 0.9300 . ?
C30 C31 1.364(3) . ?
C30 H30 0.9300 . ?
C31 O1 1.382(3) . ?
C32 C37 1.368(3) . ?
C32 O1 1.387(3) . ?
C32 C33 1.385(3) . ?
C33 C34 1.382(3) . ?
C33 N4 1.407(3) . ?
C34 C35 1.381(4) . ?
C34 H34 0.9300 . ?
C35 C36 1.369(4) . ?
C35 H35 0.9300 . ?
C36 C37 1.374(4) . ?
C36 H36 0.9300 . ?
C37 H37 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 C1 C2 119.9(3) . . ?
C6 C1 H1 120.1 . . ?
C2 C1 H1 120.1 . . ?
C3 C2 C1 120.2(3) . . ?
C3 C2 H2 119.9 . . ?
C1 C2 H2 119.9 . . ?
C4 C3 C2 120.6(3) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C3 C4 C5 119.7(3) . . ?
C3 C4 H4 120.2 . . ?
C5 C4 H4 120.2 . . ?
C4 C5 C6 120.7(3) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C1 C6 C5 118.9(2) . . ?
C1 C6 C7 120.0(3) . . ?
C5 C6 C7 121.1(2) . . ?
N1 C7 C8 120.9(2) . . ?
N1 C7 C6 116.1(2) . . ?
C8 C7 C6 123.0(2) . . ?
C9 C8 C7 119.6(2) . . ?
C9 C8 C18 118.1(2) . . ?
C7 C8 C18 122.2(2) . . ?
C10 C9 C8 118.1(2) . . ?
C10 C9 C20 122.3(2) . . ?
C8 C9 C20 119.6(2) . . ?
C9 C10 C11 119.4(2) . . ?
C9 C10 C19 118.8(2) . . ?
C11 C10 C19 121.6(2) . . ?
N1 C11 C10 121.0(2) . . ?
N1 C11 C12 115.8(2) . . ?
C10 C11 C12 123.2(2) . . ?
C13 C12 C17 118.8(2) . . ?
C13 C12 C11 121.6(2) . . ?
C17 C12 C11 119.6(2) . . ?
C12 C13 C14 120.4(3) . . ?
C12 C13 H13 119.8 . . ?
C14 C13 H13 119.8 . . ?
C15 C14 C13 119.9(3) . . ?
C15 C14 H14 120.1 . . ?
C13 C14 H14 120.1 . . ?
C14 C15 C16 120.7(3) . . ?
C14 C15 H15 119.7 . . ?
C16 C15 H15 119.7 . . ?
C15 C16 C17 119.7(3) . . ?
C15 C16 H16 120.1 . . ?
C17 C16 H16 120.1 . . ?
C16 C17 C12 120.6(3) . . ?
C16 C17 H17 119.7 . . ?
C12 C17 H17 119.7 . . ?
N2 C18 C8 176.3(3) . . ?
N3 C19 C10 176.7(3) . . ?
C25 C20 C21 118.7(2) . . ?
C25 C20 C9 121.1(2) . . ?
C21 C20 C9 120.0(2) . . ?
C22 C21 C20 121.0(2) . . ?
C22 C21 H21 119.5 . . ?
C20 C21 H21 119.5 . . ?
C21 C22 C23 119.6(3) . . ?
C21 C22 H22 120.2 . . ?
C23 C22 H22 120.2 . . ?
C24 C23 C22 120.1(2) . . ?
C24 C23 N4 120.0(2) . . ?
C22 C23 N4 119.9(2) . . ?
C23 C24 C25 119.9(2) . . ?
C23 C24 H24 120.1 . . ?
C25 C24 H24 120.1 . . ?
C20 C25 C24 120.6(2) . . ?
C20 C25 H25 119.7 . . ?
C24 C25 H25 119.7 . . ?
C27 C26 C31 117.6(2) . . ?
C27 C26 N4 123.4(2) . . ?
C31 C26 N4 119.0(2) . . ?
C28 C27 C26 120.8(2) . . ?
C28 C27 H27 119.6 . . ?
C26 C27 H27 119.6 . . ?
C29 C28 C27 120.8(3) . . ?
C29 C28 H28 119.6 . . ?
C27 C28 H28 119.6 . . ?
C28 C29 C30 118.7(2) . . ?
C28 C29 H29 120.7 . . ?
C30 C29 H29 120.7 . . ?
C31 C30 C29 121.1(2) . . ?
C31 C30 H30 119.5 . . ?
C29 C30 H30 119.5 . . ?
C30 C31 O1 117.5(2) . . ?
C30 C31 C26 120.9(2) . . ?
O1 C31 C26 121.5(2) . . ?
C37 C32 O1 116.9(2) . . ?
C37 C32 C33 121.4(2) . . ?
O1 C32 C33 121.7(2) . . ?
C34 C33 C32 118.0(2) . . ?
C34 C33 N4 123.4(2) . . ?
C32 C33 N4 118.7(2) . . ?
C33 C34 C35 120.9(3) . . ?
C33 C34 H34 119.5 . . ?
C35 C34 H34 119.5 . . ?
C36 C35 C34 119.7(3) . . ?
C36 C35 H35 120.1 . . ?
C34 C35 H35 120.1 . . ?
C35 C36 C37 120.3(3) . . ?
C35 C36 H36 119.9 . . ?
C37 C36 H36 119.9 . . ?
C32 C37 C36 119.7(3) . . ?
C32 C37 H37 120.2 . . ?
C36 C37 H37 120.2 . . ?
C7 N1 C11 120.4(2) . . ?
C26 N4 C33 119.04(19) . . ?
C26 N4 C23 119.96(19) . . ?
C33 N4 C23 117.97(19) . . ?
C31 O1 C32 117.64(18) . . ?

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
C6 C1 C2 C3 -1.4(6) . . . . ?
C1 C2 C3 C4 0.6(6) . . . . ?
C2 C3 C4 C5 0.2(5) . . . . ?
C3 C4 C5 C6 -0.1(5) . . . . ?
C2 C1 C6 C5 1.5(5) . . . . ?
C2 C1 C6 C7 179.9(3) . . . . ?
C4 C5 C6 C1 -0.7(4) . . . . ?
C4 C5 C6 C7 -179.2(2) . . . . ?
C1 C6 C7 N1 -33.6(4) . . . . ?
C5 C6 C7 N1 144.9(2) . . . . ?
C1 C6 C7 C8 145.0(3) . . . . ?
C5 C6 C7 C8 -36.6(4) . . . . ?
N1 C7 C8 C9 -7.9(4) . . . . ?
C6 C7 C8 C9 173.6(2) . . . . ?
N1 C7 C8 C18 167.6(2) . . . . ?
C6 C7 C8 C18 -10.9(4) . . . . ?
C7 C8 C9 C10 4.1(3) . . . . ?
C18 C8 C9 C10 -171.5(2) . . . . ?
C7 C8 C9 C20 -176.1(2) . . . . ?
C18 C8 C9 C20 8.3(3) . . . . ?
C8 C9 C10 C11 3.4(4) . . . . ?
C20 C9 C10 C11 -176.5(2) . . . . ?
C8 C9 C10 C19 -173.0(2) . . . . ?
C20 C9 C10 C19 7.2(4) . . . . ?
C9 C10 C11 N1 -7.6(4) . . . . ?
C19 C10 C11 N1 168.6(2) . . . . ?
C9 C10 C11 C12 171.4(2) . . . . ?
C19 C10 C11 C12 -12.4(4) . . . . ?
N1 C11 C12 C13 137.6(2) . . . . ?
C10 C11 C12 C13 -41.5(4) . . . . ?
N1 C11 C12 C17 -39.7(3) . . . . ?
C10 C11 C12 C17 141.2(2) . . . . ?
C17 C12 C13 C14 -0.7(4) . . . . ?
C11 C12 C13 C14 -178.0(2) . . . . ?
C12 C13 C14 C15 -0.6(4) . . . . ?
C13 C14 C15 C16 0.8(5) . . . . ?
C14 C15 C16 C17 0.2(5) . . . . ?
C15 C16 C17 C12 -1.5(4) . . . . ?
C13 C12 C17 C16 1.7(4) . . . . ?
C11 C12 C17 C16 179.1(2) . . . . ?
C10 C9 C20 C25 66.4(3) . . . . ?
C8 C9 C20 C25 -113.5(3) . . . . ?
C10 C9 C20 C21 -117.3(3) . . . . ?
C8 C9 C20 C21 62.9(3) . . . . ?
C25 C20 C21 C22 -0.1(4) . . . . ?
C9 C20 C21 C22 -176.6(2) . . . . ?
C20 C21 C22 C23 1.7(4) . . . . ?
C21 C22 C23 C24 -1.5(4) . . . . ?
C21 C22 C23 N4 177.5(2) . . . . ?
C22 C23 C24 C25 -0.2(4) . . . . ?
N4 C23 C24 C25 -179.2(2) . . . . ?
C21 C20 C25 C24 -1.6(4) . . . . ?
C9 C20 C25 C24 174.8(2) . . . . ?
C23 C24 C25 C20 1.7(4) . . . . ?
C31 C26 C27 C28 0.9(4) . . . . ?
N4 C26 C27 C28 -176.9(2) . . . . ?
C26 C27 C28 C29 -0.6(4) . . . . ?
C27 C28 C29 C30 0.1(4) . . . . ?
C28 C29 C30 C31 0.0(4) . . . . ?
C29 C30 C31 O1 179.4(2) . . . . ?
C29 C30 C31 C26 0.4(4) . . . . ?
C27 C26 C31 C30 -0.8(4) . . . . ?
N4 C26 C31 C30 177.1(2) . . . . ?
C27 C26 C31 O1 -179.8(2) . . . . ?
N4 C26 C31 O1 -1.9(4) . . . . ?
C37 C32 C33 C34 -0.5(4) . . . . ?
O1 C32 C33 C34 178.9(2) . . . . ?
C37 C32 C33 N4 -179.5(2) . . . . ?
O1 C32 C33 N4 -0.1(4) . . . . ?
C32 C33 C34 C35 -0.1(4) . . . . ?
N4 C33 C34 C35 178.8(3) . . . . ?
C33 C34 C35 C36 0.0(4) . . . . ?
C34 C35 C36 C37 0.7(5) . . . . ?
O1 C32 C37 C36 -178.2(2) . . . . ?
C33 C32 C37 C36 1.2(4) . . . . ?
C35 C36 C37 C32 -1.3(4) . . . . ?
C8 C7 N1 C11 3.7(4) . . . . ?
C6 C7 N1 C11 -177.7(2) . . . . ?
C10 C11 N1 C7 4.0(4) . . . . ?
C12 C11 N1 C7 -175.1(2) . . . . ?
C27 C26 N4 C33 -168.2(2) . . . . ?
C31 C26 N4 C33 14.0(4) . . . . ?
C27 C26 N4 C23 -8.2(4) . . . . ?
C31 C26 N4 C23 174.0(2) . . . . ?
C34 C33 N4 C26 168.0(2) . . . . ?
C32 C33 N4 C26 -13.1(4) . . . . ?
C34 C33 N4 C23 7.7(4) . . . . ?
C32 C33 N4 C23 -173.4(2) . . . . ?
C24 C23 N4 C26 112.0(3) . . . . ?
C22 C23 N4 C26 -67.0(3) . . . . ?
C24 C23 N4 C33 -87.8(3) . . . . ?
C22 C23 N4 C33 93.2(3) . . . . ?
C30 C31 O1 C32 170.0(2) . . . . ?
C26 C31 O1 C32 -11.0(3) . . . . ?
C37 C32 O1 C31 -168.6(2) . . . . ?
C33 C32 O1 C31 12.0(3) . . . . ?

_refine_diff_density_max         0.147
_refine_diff_density_min         -0.204
_refine_diff_density_rms         0.043



####################################################################### 
# 
# 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_1_a_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1821567'
_audit_update_record             
;
2018-02-02 deposited with the CCDC.
2018-05-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C52 H32 Cl9 N5 O2'
_chemical_formula_weight         1077.87

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

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

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

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

_cell_length_a                   10.3134(9)
_cell_length_b                   13.4390(10)
_cell_length_c                   18.0482(15)
_cell_angle_alpha                80.535(3)
_cell_angle_beta                 88.487(3)
_cell_angle_gamma                83.795(3)
_cell_volume                     2452.9(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1373
_cell_measurement_theta_min      2.38
_cell_measurement_theta_max      20.30

_exptl_crystal_description       Block
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.459
_exptl_crystal_F_000             1096
_exptl_transmission_factor_min   0.864
_exptl_transmission_factor_max   0.864
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    0.561
_shelx_estimated_absorpt_T_min   0.886
_shelx_estimated_absorpt_T_max   0.906
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  CCD
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15960
_diffrn_reflns_av_unetI/netI     0.0916
_diffrn_reflns_av_R_equivalents  0.0445
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.144
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        24.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             8604
_reflns_number_gt                3812
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         8604
_refine_ls_number_parameters     598
_refine_ls_number_restraints     62
_refine_ls_R_factor_all          0.2118
_refine_ls_R_factor_gt           0.1318
_refine_ls_wR_factor_ref         0.4173
_refine_ls_wR_factor_gt          0.3557
_refine_ls_goodness_of_fit_ref   1.204
_refine_ls_restrained_S_all      1.209
_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
C1 C 0.9840(8) 0.3130(4) 0.7783(4) 0.0649(19) Uani 1 1 d . . . . .
H1 H 0.8942 0.3226 0.7858 0.078 Uiso 1 1 calc R U . . .
C2 C 1.0482(11) 0.2154(5) 0.7872(4) 0.081(3) Uani 1 1 d . . . . .
H2 H 1.0012 0.1599 0.8011 0.097 Uiso 1 1 calc R U . . .
C3 C 1.1804(11) 0.2004(6) 0.7757(5) 0.086(3) Uani 1 1 d . . . . .
H3 H 1.2224 0.1349 0.7808 0.104 Uiso 1 1 calc R U . . .
C4 C 1.2502(9) 0.2816(6) 0.7567(5) 0.089(3) Uani 1 1 d . . . . .
H4 H 1.3401 0.2712 0.7503 0.107 Uiso 1 1 calc R U . . .
C5 C 1.1885(8) 0.3786(5) 0.7470(4) 0.072(2) Uani 1 1 d . . . . .
H5 H 1.2364 0.4336 0.7329 0.087 Uiso 1 1 calc R U . . .
C6 C 1.0532(7) 0.3951(4) 0.7584(3) 0.0524(16) Uani 1 1 d . . . . .
C7 C 0.9870(6) 0.5008(4) 0.7477(3) 0.0481(15) Uani 1 1 d . . . . .
C8 C 0.9220(6) 0.5405(4) 0.8070(3) 0.0472(15) Uani 1 1 d . . . . .
C9 C 0.8676(6) 0.6417(4) 0.7963(3) 0.0421(13) Uani 1 1 d . . . . .
C10 C 0.9154(6) 0.6612(4) 0.6686(3) 0.0449(14) Uani 1 1 d . . . . .
C11 C 0.9869(6) 0.5632(4) 0.6785(3) 0.0464(15) Uani 1 1 d . . . . .
C12 C 1.0634(7) 0.5288(4) 0.6169(4) 0.0564(17) Uani 1 1 d . . . . .
C13 C 0.9135(7) 0.4772(4) 0.8792(4) 0.0571(17) Uani 1 1 d . . . . .
C14 C 0.8967(6) 0.7270(4) 0.5953(3) 0.0450(14) Uani 1 1 d . . . . .
C15 C 0.8922(6) 0.8320(4) 0.5918(3) 0.0494(15) Uani 1 1 d . . . . .
H15 H 0.9051 0.8588 0.6350 0.059 Uiso 1 1 calc R U . . .
C16 C 0.8690(6) 0.8957(4) 0.5249(3) 0.0539(16) Uani 1 1 d . . . . .
H16 H 0.8671 0.9654 0.5232 0.065 Uiso 1 1 calc R U . . .
C17 C 0.8483(6) 0.8576(4) 0.4596(3) 0.0481(15) Uani 1 1 d . . . . .
C18 C 0.8494(7) 0.7559(5) 0.4628(3) 0.0579(17) Uani 1 1 d . . . . .
H18 H 0.8338 0.7300 0.4195 0.069 Uiso 1 1 calc R U . . .
C19 C 0.8735(7) 0.6899(4) 0.5300(3) 0.0544(17) Uani 1 1 d . . . . .
H19 H 0.8741 0.6204 0.5313 0.065 Uiso 1 1 calc R U . . .
C20 C 0.9288(6) 0.9553(4) 0.3446(3) 0.0447(14) Uani 1 1 d . . . . .
C21 C 1.0548(6) 0.9101(5) 0.3568(3) 0.0540(16) Uani 1 1 d . . . . .
H21 H 1.0722 0.8588 0.3977 0.065 Uiso 1 1 calc R U . . .
C22 C 1.1565(6) 0.9404(5) 0.3086(4) 0.0631(18) Uani 1 1 d . . . . .
H22 H 1.2408 0.9096 0.3183 0.076 Uiso 1 1 calc R U . . .
C23 C 1.1341(7) 1.0132(5) 0.2487(4) 0.0637(18) Uani 1 1 d . . . . .
H23 H 1.2020 1.0324 0.2163 0.076 Uiso 1 1 calc R U . . .
C24 C 1.0082(7) 1.0596(5) 0.2357(4) 0.0603(17) Uani 1 1 d . . . . .
H24 H 0.9917 1.1102 0.1942 0.072 Uiso 1 1 calc R U . . .
C25 C 0.9074(6) 1.0318(4) 0.2832(3) 0.0477(15) Uani 1 1 d . . . . .
C26 C 0.6824(6) 1.0506(5) 0.3123(3) 0.0525(16) Uani 1 1 d . . . . .
C27 C 0.5616(7) 1.0999(6) 0.2929(4) 0.071(2) Uani 1 1 d . . . . .
H27 H 0.5524 1.1512 0.2514 0.085 Uiso 1 1 calc R U . . .
C28 C 0.4540(7) 1.0732(7) 0.3353(4) 0.079(2) Uani 1 1 d . . . . .
H28 H 0.3718 1.1067 0.3230 0.095 Uiso 1 1 calc R U . . .
C29 C 0.4691(7) 0.9967(7) 0.3957(4) 0.079(2) Uani 1 1 d . . . . .
H29 H 0.3966 0.9788 0.4245 0.095 Uiso 1 1 calc R U . . .
C30 C 0.5902(6) 0.9459(5) 0.4146(4) 0.0652(19) Uani 1 1 d . . . . .
H30 H 0.5983 0.8931 0.4552 0.078 Uiso 1 1 calc R U . . .
C31 C 0.6990(6) 0.9731(4) 0.3736(3) 0.0496(15) Uani 1 1 d . . . . .
C32 C 0.8133(6) 0.6960(4) 0.8576(3) 0.0440(14) Uani 1 1 d . . . . .
C33 C 0.8753(6) 0.6857(5) 0.9267(3) 0.0542(16) Uani 1 1 d . . . . .
H33 H 0.9497 0.6401 0.9366 0.065 Uiso 1 1 calc R U . . .
C34 C 0.8271(7) 0.7427(5) 0.9804(4) 0.0614(18) Uani 1 1 d . . . . .
H34 H 0.8675 0.7343 1.0269 0.074 Uiso 1 1 calc R U . . .
C35 C 0.7187(7) 0.8123(5) 0.9648(4) 0.0610(18) Uani 1 1 d . . . . .
C36 C 0.6562(7) 0.8230(5) 0.8964(4) 0.0630(19) Uani 1 1 d . . . . .
H36 H 0.5824 0.8690 0.8860 0.076 Uiso 1 1 calc R U . . .
C37 C 0.7054(6) 0.7644(5) 0.8439(3) 0.0537(16) Uani 1 1 d . . . . .
H37 H 0.6638 0.7718 0.7980 0.064 Uiso 1 1 calc R U . . .
C38 C 0.7275(7) 0.9678(5) 1.0203(3) 0.0577(17) Uani 1 1 d . . . . .
C39 C 0.6893(7) 1.0227(5) 1.0764(4) 0.0594(17) Uani 1 1 d . . . . .
C40 C 0.7397(9) 1.1135(6) 1.0795(5) 0.078(2) Uani 1 1 d . . . . .
H40 H 0.7126 1.1507 1.1173 0.094 Uiso 1 1 calc R U . . .
C41 C 0.8289(10) 1.1483(8) 1.0272(6) 0.102(3) Uani 1 1 d . . . . .
H41 H 0.8608 1.2100 1.0290 0.122 Uiso 1 1 calc R U . . .
C42 C 0.8722(12) 1.0934(8) 0.9719(5) 0.112(3) Uani 1 1 d . . . . .
H42 H 0.9370 1.1154 0.9383 0.135 Uiso 1 1 calc R U . . .
C43 C 0.8170(8) 1.0035(6) 0.9669(4) 0.079(2) Uani 1 1 d . . . . .
H43 H 0.8408 0.9682 0.9277 0.095 Uiso 1 1 calc R U . . .
C44 C 0.5746(7) 0.8482(5) 1.0709(4) 0.0579(17) Uani 1 1 d . . . . .
C45 C 0.5410(7) 0.9077(5) 1.1274(4) 0.0601(18) Uani 1 1 d . . . . .
C46 C 0.4464(8) 0.8809(7) 1.1795(5) 0.079(2) Uani 1 1 d . . . . .
H46 H 0.4260 0.9201 1.2170 0.094 Uiso 1 1 calc R U . . .
C47 C 0.3839(9) 0.8009(9) 1.1776(5) 0.106(3) Uani 1 1 d . . . . .
H47 H 0.3192 0.7850 1.2131 0.127 Uiso 1 1 calc R U . . .
C48 C 0.4137(9) 0.7403(8) 1.1234(5) 0.101(3) Uani 1 1 d . . . . .
H48 H 0.3700 0.6835 1.1226 0.121 Uiso 1 1 calc R U . . .
C49 C 0.5100(7) 0.7650(6) 1.0697(4) 0.073(2) Uani 1 1 d . . . . .
H49 H 0.5302 0.7245 1.0330 0.087 Uiso 1 1 calc R U . . .
C50 C 0.6315(9) 0.4642(15) 0.6177(10) 0.326(15) Uiso 1 1 d D . . . .
H50 H 0.6371 0.5244 0.5794 0.391 Uiso 1 1 calc R U . . .
C51 C 0.6475(11) 0.3175(15) 0.4278(8) 0.42(2) Uiso 1 1 d D . . . .
H51 H 0.6623 0.3771 0.4499 0.500 Uiso 1 1 calc R U . . .
C52 C 0.7012(9) 0.4117(11) 0.0917(7) 0.164(5) Uiso 1 1 d D . . . .
H52 H 0.7386 0.3873 0.0467 0.197 Uiso 1 1 calc R U . . .
Cl1 Cl 0.6253(9) 0.4944(11) 0.7102(7) 0.421(6) Uani 1 1 d D . . . .
Cl2 Cl 0.4885(8) 0.4043(11) 0.6080(6) 0.497(10) Uani 1 1 d D . . . .
Cl3 Cl 0.7679(7) 0.3725(7) 0.6143(4) 0.327(4) Uani 1 1 d D . . . .
Cl4 Cl 0.7433(10) 0.2055(7) 0.4694(6) 0.368(5) Uani 1 1 d D . . . .
Cl5 Cl 0.4828(9) 0.2887(9) 0.4364(8) 0.482(9) Uani 1 1 d D . . . .
Cl6 Cl 0.6852(13) 0.3314(12) 0.3300(6) 0.559(10) Uani 1 1 d D U . . .
Cl7 Cl 0.7799(5) 0.3382(3) 0.1736(3) 0.222(2) Uani 1 1 d D . . . .
Cl8 Cl 0.5334(5) 0.3855(5) 0.1022(4) 0.258(3) Uani 1 1 d D . . . .
Cl9 Cl 0.7237(6) 0.5259(3) 0.0878(3) 0.217(2) Uani 1 1 d D . . . .
N1 N 0.9025(7) 0.4247(4) 0.9349(4) 0.082(2) Uani 1 1 d . . . . .
N2 N 1.1265(7) 0.5016(5) 0.5693(4) 0.085(2) Uani 1 1 d . . . . .
N3 N 0.8620(5) 0.6975(3) 0.7279(3) 0.0456(12) Uani 1 1 d . . . . .
N4 N 0.6744(6) 0.8762(4) 1.0189(3) 0.0722(17) Uani 1 1 d . . . . .
N5 N 0.8259(5) 0.9264(4) 0.3914(3) 0.0560(14) Uani 1 1 d . . . . .
O1 O 0.6035(5) 0.9918(4) 1.1321(3) 0.0733(14) Uani 1 1 d . . . . .
O2 O 0.7873(5) 1.0816(4) 0.2683(3) 0.0764(15) 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
C1 C6 1.372(9) . ?
C1 C2 1.390(10) . ?
C1 H1 0.9300 . ?
C2 C3 1.371(12) . ?
C2 H2 0.9300 . ?
C3 C4 1.364(13) . ?
C3 H3 0.9300 . ?
C4 C5 1.374(10) . ?
C4 H4 0.9300 . ?
C5 C6 1.403(10) . ?
C5 H5 0.9300 . ?
C6 C7 1.494(8) . ?
C7 C11 1.384(8) . ?
C7 C8 1.398(8) . ?
C8 C9 1.399(8) . ?
C8 C13 1.440(9) . ?
C9 N3 1.334(7) . ?
C9 C32 1.488(8) . ?
C10 N3 1.331(7) . ?
C10 C11 1.426(8) . ?
C10 C14 1.469(8) . ?
C11 C12 1.455(9) . ?
C12 N2 1.148(8) . ?
C13 N1 1.140(8) . ?
C14 C19 1.389(8) . ?
C14 C15 1.398(8) . ?
C15 C16 1.370(8) . ?
C15 H15 0.9300 . ?
C16 C17 1.390(8) . ?
C16 H16 0.9300 . ?
C17 C18 1.358(8) . ?
C17 N5 1.420(7) . ?
C18 C19 1.391(8) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C20 C21 1.381(8) . ?
C20 N5 1.387(7) . ?
C20 C25 1.388(8) . ?
C21 C22 1.396(9) . ?
C21 H21 0.9300 . ?
C22 C23 1.341(10) . ?
C22 H22 0.9300 . ?
C23 C24 1.387(9) . ?
C23 H23 0.9300 . ?
C24 C25 1.373(9) . ?
C24 H24 0.9300 . ?
C25 O2 1.354(7) . ?
C26 C31 1.389(8) . ?
C26 C27 1.372(9) . ?
C26 O2 1.385(8) . ?
C27 C28 1.377(10) . ?
C27 H27 0.9300 . ?
C28 C29 1.369(11) . ?
C28 H28 0.9300 . ?
C29 C30 1.380(9) . ?
C29 H29 0.9300 . ?
C30 C31 1.378(9) . ?
C30 H30 0.9300 . ?
C31 N5 1.409(7) . ?
C32 C37 1.366(8) . ?
C32 C33 1.396(8) . ?
C33 C34 1.384(8) . ?
C33 H33 0.9300 . ?
C34 C35 1.381(9) . ?
C34 H34 0.9300 . ?
C35 C36 1.387(9) . ?
C35 N4 1.438(8) . ?
C36 C37 1.380(9) . ?
C36 H36 0.9300 . ?
C37 H37 0.9300 . ?
C38 C39 1.374(9) . ?
C38 C43 1.381(10) . ?
C38 N4 1.404(9) . ?
C39 O1 1.365(8) . ?
C39 C40 1.387(10) . ?
C40 C41 1.363(12) . ?
C40 H40 0.9300 . ?
C41 C42 1.374(13) . ?
C41 H41 0.9300 . ?
C42 C43 1.407(12) . ?
C42 H42 0.9300 . ?
C43 H43 0.9300 . ?
C44 C49 1.366(10) . ?
C44 N4 1.413(8) . ?
C44 C45 1.410(9) . ?
C45 C46 1.371(10) . ?
C45 O1 1.376(9) . ?
C46 C47 1.318(12) . ?
C46 H46 0.9300 . ?
C47 C48 1.380(12) . ?
C47 H47 0.9300 . ?
C48 C49 1.395(11) . ?
C48 H48 0.9300 . ?
C49 H49 0.9300 . ?
C50 Cl3 1.774(10) . ?
C50 Cl1 1.779(10) . ?
C50 Cl2 1.780(10) . ?
C50 H50 0.9800 . ?
C51 Cl4 1.775(11) . ?
C51 Cl5 1.779(11) . ?
C51 Cl6 1.781(10) . ?
C51 H51 0.9800 . ?
C52 Cl9 1.567(14) . ?
C52 Cl7 1.797(9) . ?
C52 Cl8 1.802(9) . ?
C52 H52 0.9800 . ?

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
C6 C1 C2 119.9(8) . . ?
C6 C1 H1 120.1 . . ?
C2 C1 H1 120.1 . . ?
C3 C2 C1 120.5(8) . . ?
C3 C2 H2 119.7 . . ?
C1 C2 H2 119.7 . . ?
C4 C3 C2 120.0(7) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C3 C4 C5 120.4(9) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C6 C5 C4 120.2(8) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
C5 C6 C1 119.0(6) . . ?
C5 C6 C7 119.7(6) . . ?
C1 C6 C7 121.2(6) . . ?
C11 C7 C8 117.4(5) . . ?
C11 C7 C6 121.3(5) . . ?
C8 C7 C6 121.3(5) . . ?
C9 C8 C7 119.8(5) . . ?
C9 C8 C13 120.5(5) . . ?
C7 C8 C13 119.6(5) . . ?
N3 C9 C8 120.9(5) . . ?
N3 C9 C32 114.8(4) . . ?
C8 C9 C32 124.4(5) . . ?
N3 C10 C11 119.7(5) . . ?
N3 C10 C14 116.7(4) . . ?
C11 C10 C14 123.7(5) . . ?
C7 C11 C10 120.2(5) . . ?
C7 C11 C12 119.4(5) . . ?
C10 C11 C12 120.4(5) . . ?
N2 C12 C11 178.3(7) . . ?
N1 C13 C8 176.8(8) . . ?
C19 C14 C15 118.2(5) . . ?
C19 C14 C10 122.7(5) . . ?
C15 C14 C10 119.0(5) . . ?
C16 C15 C14 120.4(5) . . ?
C16 C15 H15 119.8 . . ?
C14 C15 H15 119.8 . . ?
C15 C16 C17 120.9(5) . . ?
C15 C16 H16 119.5 . . ?
C17 C16 H16 119.5 . . ?
C18 C17 C16 119.2(5) . . ?
C18 C17 N5 121.8(6) . . ?
C16 C17 N5 119.0(5) . . ?
C17 C18 C19 120.7(6) . . ?
C17 C18 H18 119.6 . . ?
C19 C18 H18 119.6 . . ?
C18 C19 C14 120.5(5) . . ?
C18 C19 H19 119.7 . . ?
C14 C19 H19 119.7 . . ?
C21 C20 N5 122.2(5) . . ?
C21 C20 C25 117.6(6) . . ?
N5 C20 C25 120.3(5) . . ?
C20 C21 C22 121.0(6) . . ?
C20 C21 H21 119.5 . . ?
C22 C21 H21 119.5 . . ?
C23 C22 C21 120.9(6) . . ?
C23 C22 H22 119.6 . . ?
C21 C22 H22 119.6 . . ?
C22 C23 C24 119.0(6) . . ?
C22 C23 H23 120.5 . . ?
C24 C23 H23 120.5 . . ?
C25 C24 C23 120.9(6) . . ?
C25 C24 H24 119.6 . . ?
C23 C24 H24 119.6 . . ?
O2 C25 C24 118.0(5) . . ?
O2 C25 C20 121.3(5) . . ?
C24 C25 C20 120.7(6) . . ?
C31 C26 C27 121.5(6) . . ?
C31 C26 O2 121.4(5) . . ?
C27 C26 O2 117.2(6) . . ?
C28 C27 C26 119.7(6) . . ?
C28 C27 H27 120.2 . . ?
C26 C27 H27 120.2 . . ?
C27 C28 C29 119.4(7) . . ?
C27 C28 H28 120.3 . . ?
C29 C28 H28 120.3 . . ?
C30 C29 C28 121.1(7) . . ?
C30 C29 H29 119.5 . . ?
C28 C29 H29 119.5 . . ?
C31 C30 C29 120.2(6) . . ?
C31 C30 H30 119.9 . . ?
C29 C30 H30 119.9 . . ?
C26 C31 C30 118.2(6) . . ?
C26 C31 N5 118.9(5) . . ?
C30 C31 N5 122.9(5) . . ?
C37 C32 C33 118.6(5) . . ?
C37 C32 C9 119.0(5) . . ?
C33 C32 C9 122.1(5) . . ?
C34 C33 C32 120.5(6) . . ?
C34 C33 H33 119.7 . . ?
C32 C33 H33 119.7 . . ?
C33 C34 C35 119.6(6) . . ?
C33 C34 H34 120.2 . . ?
C35 C34 H34 120.2 . . ?
C36 C35 C34 120.3(6) . . ?
C36 C35 N4 120.4(6) . . ?
C34 C35 N4 119.3(6) . . ?
C35 C36 C37 119.0(6) . . ?
C35 C36 H36 120.5 . . ?
C37 C36 H36 120.5 . . ?
C32 C37 C36 121.9(6) . . ?
C32 C37 H37 119.0 . . ?
C36 C37 H37 119.0 . . ?
C39 C38 C43 119.5(7) . . ?
C39 C38 N4 118.9(6) . . ?
C43 C38 N4 121.7(6) . . ?
O1 C39 C38 123.2(6) . . ?
O1 C39 C40 116.4(6) . . ?
C38 C39 C40 120.4(7) . . ?
C41 C40 C39 120.1(8) . . ?
C41 C40 H40 120.0 . . ?
C39 C40 H40 120.0 . . ?
C42 C41 C40 120.8(9) . . ?
C42 C41 H41 119.6 . . ?
C40 C41 H41 119.6 . . ?
C41 C42 C43 119.0(9) . . ?
C41 C42 H42 120.5 . . ?
C43 C42 H42 120.5 . . ?
C38 C43 C42 120.0(8) . . ?
C38 C43 H43 120.0 . . ?
C42 C43 H43 120.0 . . ?
C49 C44 N4 123.0(6) . . ?
C49 C44 C45 118.1(7) . . ?
N4 C44 C45 118.9(6) . . ?
C46 C45 O1 119.0(6) . . ?
C46 C45 C44 120.0(7) . . ?
O1 C45 C44 121.0(6) . . ?
C47 C46 C45 121.4(8) . . ?
C47 C46 H46 119.3 . . ?
C45 C46 H46 119.3 . . ?
C46 C47 C48 120.6(8) . . ?
C46 C47 H47 119.7 . . ?
C48 C47 H47 119.7 . . ?
C47 C48 C49 119.5(8) . . ?
C47 C48 H48 120.2 . . ?
C49 C48 H48 120.2 . . ?
C44 C49 C48 120.3(7) . . ?
C44 C49 H49 119.8 . . ?
C48 C49 H49 119.8 . . ?
Cl3 C50 Cl1 106.6(8) . . ?
Cl3 C50 Cl2 107.7(9) . . ?
Cl1 C50 Cl2 106.1(9) . . ?
Cl3 C50 H50 112.0 . . ?
Cl1 C50 H50 112.0 . . ?
Cl2 C50 H50 112.0 . . ?
Cl4 C51 Cl5 105.8(9) . . ?
Cl4 C51 Cl6 105.5(9) . . ?
Cl5 C51 Cl6 105.8(9) . . ?
Cl4 C51 H51 113.0 . . ?
Cl5 C51 H51 113.0 . . ?
Cl6 C51 H51 113.0 . . ?
Cl9 C52 Cl7 109.3(7) . . ?
Cl9 C52 Cl8 115.1(7) . . ?
Cl7 C52 Cl8 104.3(7) . . ?
Cl9 C52 H52 109.3 . . ?
Cl7 C52 H52 109.3 . . ?
Cl8 C52 H52 109.3 . . ?
C10 N3 C9 121.3(4) . . ?
C38 N4 C44 119.0(5) . . ?
C38 N4 C35 120.9(6) . . ?
C44 N4 C35 120.1(6) . . ?
C20 N5 C17 120.9(5) . . ?
C20 N5 C31 118.9(5) . . ?
C17 N5 C31 120.0(5) . . ?
C39 O1 C45 118.4(5) . . ?
C25 O2 C26 119.1(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
C6 C1 C2 C3 -0.5(11) . . . . ?
C1 C2 C3 C4 1.2(12) . . . . ?
C2 C3 C4 C5 -1.7(13) . . . . ?
C3 C4 C5 C6 1.6(12) . . . . ?
C4 C5 C6 C1 -0.8(11) . . . . ?
C4 C5 C6 C7 -180.0(7) . . . . ?
C2 C1 C6 C5 0.3(10) . . . . ?
C2 C1 C6 C7 179.4(6) . . . . ?
C5 C6 C7 C11 62.3(8) . . . . ?
C1 C6 C7 C11 -116.8(7) . . . . ?
C5 C6 C7 C8 -118.1(7) . . . . ?
C1 C6 C7 C8 62.8(8) . . . . ?
C11 C7 C8 C9 -4.1(9) . . . . ?
C6 C7 C8 C9 176.3(6) . . . . ?
C11 C7 C8 C13 176.9(6) . . . . ?
C6 C7 C8 C13 -2.7(9) . . . . ?
C7 C8 C9 N3 8.7(9) . . . . ?
C13 C8 C9 N3 -172.3(6) . . . . ?
C7 C8 C9 C32 -170.9(6) . . . . ?
C13 C8 C9 C32 8.1(9) . . . . ?
C8 C7 C11 C10 -4.0(9) . . . . ?
C6 C7 C11 C10 175.6(6) . . . . ?
C8 C7 C11 C12 174.3(6) . . . . ?
C6 C7 C11 C12 -6.1(9) . . . . ?
N3 C10 C11 C7 8.2(9) . . . . ?
C14 C10 C11 C7 -172.2(6) . . . . ?
N3 C10 C11 C12 -170.1(6) . . . . ?
C14 C10 C11 C12 9.6(9) . . . . ?
N3 C10 C14 C19 -141.0(6) . . . . ?
C11 C10 C14 C19 39.3(10) . . . . ?
N3 C10 C14 C15 34.1(8) . . . . ?
C11 C10 C14 C15 -145.6(6) . . . . ?
C19 C14 C15 C16 -1.7(10) . . . . ?
C10 C14 C15 C16 -177.0(6) . . . . ?
C14 C15 C16 C17 0.6(10) . . . . ?
C15 C16 C17 C18 1.0(10) . . . . ?
C15 C16 C17 N5 -179.4(6) . . . . ?
C16 C17 C18 C19 -1.3(10) . . . . ?
N5 C17 C18 C19 179.1(6) . . . . ?
C17 C18 C19 C14 0.1(11) . . . . ?
C15 C14 C19 C18 1.4(10) . . . . ?
C10 C14 C19 C18 176.5(6) . . . . ?
N5 C20 C21 C22 179.7(6) . . . . ?
C25 C20 C21 C22 -0.3(9) . . . . ?
C20 C21 C22 C23 -0.9(10) . . . . ?
C21 C22 C23 C24 1.0(11) . . . . ?
C22 C23 C24 C25 0.0(10) . . . . ?
C23 C24 C25 O2 178.6(6) . . . . ?
C23 C24 C25 C20 -1.2(10) . . . . ?
C21 C20 C25 O2 -178.4(6) . . . . ?
N5 C20 C25 O2 1.6(9) . . . . ?
C21 C20 C25 C24 1.3(9) . . . . ?
N5 C20 C25 C24 -178.6(6) . . . . ?
C31 C26 C27 C28 0.6(11) . . . . ?
O2 C26 C27 C28 -179.2(7) . . . . ?
C26 C27 C28 C29 -0.8(12) . . . . ?
C27 C28 C29 C30 -0.3(13) . . . . ?
C28 C29 C30 C31 1.5(12) . . . . ?
C27 C26 C31 C30 0.5(10) . . . . ?
O2 C26 C31 C30 -179.7(6) . . . . ?
C27 C26 C31 N5 -179.0(6) . . . . ?
O2 C26 C31 N5 0.8(9) . . . . ?
C29 C30 C31 C26 -1.6(10) . . . . ?
C29 C30 C31 N5 177.9(6) . . . . ?
N3 C9 C32 C37 37.1(8) . . . . ?
C8 C9 C32 C37 -143.3(6) . . . . ?
N3 C9 C32 C33 -137.3(6) . . . . ?
C8 C9 C32 C33 42.2(9) . . . . ?
C37 C32 C33 C34 0.9(9) . . . . ?
C9 C32 C33 C34 175.4(6) . . . . ?
C32 C33 C34 C35 -1.7(10) . . . . ?
C33 C34 C35 C36 1.7(10) . . . . ?
C33 C34 C35 N4 -175.8(6) . . . . ?
C34 C35 C36 C37 -1.0(10) . . . . ?
N4 C35 C36 C37 176.4(6) . . . . ?
C33 C32 C37 C36 -0.2(9) . . . . ?
C9 C32 C37 C36 -174.8(6) . . . . ?
C35 C36 C37 C32 0.3(10) . . . . ?
C43 C38 C39 O1 -178.6(6) . . . . ?
N4 C38 C39 O1 1.3(10) . . . . ?
C43 C38 C39 C40 0.1(10) . . . . ?
N4 C38 C39 C40 -180.0(6) . . . . ?
O1 C39 C40 C41 178.1(7) . . . . ?
C38 C39 C40 C41 -0.7(11) . . . . ?
C39 C40 C41 C42 -1.4(14) . . . . ?
C40 C41 C42 C43 4.0(16) . . . . ?
C39 C38 C43 C42 2.5(11) . . . . ?
N4 C38 C43 C42 -177.4(8) . . . . ?
C41 C42 C43 C38 -4.6(14) . . . . ?
C49 C44 C45 C46 0.5(10) . . . . ?
N4 C44 C45 C46 -178.6(6) . . . . ?
C49 C44 C45 O1 179.2(6) . . . . ?
N4 C44 C45 O1 0.1(9) . . . . ?
O1 C45 C46 C47 -179.8(8) . . . . ?
C44 C45 C46 C47 -1.0(12) . . . . ?
C45 C46 C47 C48 1.1(15) . . . . ?
C46 C47 C48 C49 -0.7(15) . . . . ?
N4 C44 C49 C48 178.9(8) . . . . ?
C45 C44 C49 C48 -0.1(11) . . . . ?
C47 C48 C49 C44 0.2(14) . . . . ?
C11 C10 N3 C9 -3.8(9) . . . . ?
C14 C10 N3 C9 176.5(5) . . . . ?
C8 C9 N3 C10 -4.5(9) . . . . ?
C32 C9 N3 C10 175.1(5) . . . . ?
C39 C38 N4 C44 5.8(10) . . . . ?
C43 C38 N4 C44 -174.3(6) . . . . ?
C39 C38 N4 C35 -175.3(6) . . . . ?
C43 C38 N4 C35 4.6(10) . . . . ?
C49 C44 N4 C38 174.5(7) . . . . ?
C45 C44 N4 C38 -6.5(9) . . . . ?
C49 C44 N4 C35 -4.4(10) . . . . ?
C45 C44 N4 C35 174.6(6) . . . . ?
C36 C35 N4 C38 -91.8(9) . . . . ?
C34 C35 N4 C38 85.7(8) . . . . ?
C36 C35 N4 C44 87.1(8) . . . . ?
C34 C35 N4 C44 -95.4(8) . . . . ?
C21 C20 N5 C17 8.2(9) . . . . ?
C25 C20 N5 C17 -171.9(6) . . . . ?
C21 C20 N5 C31 -177.4(5) . . . . ?
C25 C20 N5 C31 2.6(8) . . . . ?
C18 C17 N5 C20 -90.9(8) . . . . ?
C16 C17 N5 C20 89.5(7) . . . . ?
C18 C17 N5 C31 94.8(7) . . . . ?
C16 C17 N5 C31 -84.9(7) . . . . ?
C26 C31 N5 C20 -3.7(9) . . . . ?
C30 C31 N5 C20 176.8(6) . . . . ?
C26 C31 N5 C17 170.8(6) . . . . ?
C30 C31 N5 C17 -8.7(10) . . . . ?
C38 C39 O1 C45 -7.7(9) . . . . ?
C40 C39 O1 C45 173.6(6) . . . . ?
C46 C45 O1 C39 -174.5(6) . . . . ?
C44 C45 O1 C39 6.8(9) . . . . ?
C24 C25 O2 C26 175.7(6) . . . . ?
C20 C25 O2 C26 -4.5(9) . . . . ?
C31 C26 O2 C25 3.3(9) . . . . ?
C27 C26 O2 C25 -176.9(6) . . . . ?

_refine_diff_density_max         0.702
_refine_diff_density_min         -0.701
_refine_diff_density_rms         0.104



