# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2014

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#                                CCDC 
# 
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# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
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#  fide research purposes only. It may contain copyright material
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data_mo_dm14121_0m

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C44 H31 N3'
_chemical_formula_weight         601.72

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'

_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                   9.5653(13)
_cell_length_b                   11.8383(16)
_cell_length_c                   14.678(2)
_cell_angle_alpha                102.839(3)
_cell_angle_beta                 96.717(3)
_cell_angle_gamma                102.722(3)
_cell_volume                     1556.5(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    140(2)
_cell_measurement_reflns_used    1697
_cell_measurement_theta_min      2.43
_cell_measurement_theta_max      27.46

_exptl_crystal_description       ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.284
_exptl_crystal_F_000             632
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.075
_shelx_estimated_absorpt_T_min   0.974
_shelx_estimated_absorpt_T_max   0.994
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5842
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      140(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15907
_diffrn_reflns_av_unetI/netI     0.0926
_diffrn_reflns_av_R_equivalents  0.0414
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.824
_diffrn_reflns_theta_max         30.647
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             9511
_reflns_number_gt                4984
_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    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_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)+(0.0566P)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         9511
_refine_ls_number_parameters     424
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1262
_refine_ls_R_factor_gt           0.0604
_refine_ls_wR_factor_ref         0.1466
_refine_ls_wR_factor_gt          0.1189
_refine_ls_goodness_of_fit_ref   0.946
_refine_ls_restrained_S_all      0.946
_refine_ls_shift/su_max          0.010
_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
N1 N 0.80054(15) 0.85042(13) 0.07928(10) 0.0285(3) Uani 1 1 d . . . . .
N2 N 0.63385(14) 0.77747(13) 0.20152(10) 0.0241(3) Uani 1 1 d . . . . .
N3 N 0.46226(15) 1.16506(13) 0.41953(10) 0.0284(3) Uani 1 1 d . . . . .
C1 C 0.65912(19) 0.76992(16) 0.04053(12) 0.0273(4) Uani 1 1 d . . . . .
C2 C 0.6150(2) 0.71935(17) -0.05984(12) 0.0309(4) Uani 1 1 d . . . . .
C3 C 0.7058(2) 0.75271(19) -0.12369(14) 0.0383(5) Uani 1 1 d . . . . .
H3 H 0.7976 0.8090 -0.1003 0.046 Uiso 1 1 calc R U . . .
C4 C 0.6616(3) 0.7041(2) -0.21933(15) 0.0460(6) Uani 1 1 d . . . . .
H4 H 0.7227 0.7268 -0.2622 0.055 Uiso 1 1 calc R U . . .
C5 C 0.5275(3) 0.6213(2) -0.25374(15) 0.0488(6) Uani 1 1 d . . . . .
H5 H 0.4974 0.5883 -0.3202 0.059 Uiso 1 1 calc R U . . .
C6 C 0.4388(2) 0.58694(19) -0.19330(14) 0.0417(5) Uani 1 1 d . . . . .
H6 H 0.3478 0.5301 -0.2183 0.050 Uiso 1 1 calc R U . . .
C7 C 0.4795(2) 0.63431(17) -0.09419(13) 0.0332(4) Uani 1 1 d . . . . .
C8 C 0.38859(19) 0.59754(16) -0.02810(13) 0.0309(4) Uani 1 1 d . . . . .
C9 C 0.2535(2) 0.51035(17) -0.05659(14) 0.0376(5) Uani 1 1 d . . . . .
H9 H 0.2189 0.4742 -0.1223 0.045 Uiso 1 1 calc R U . . .
C10 C 0.1716(2) 0.47672(18) 0.00738(15) 0.0400(5) Uani 1 1 d . . . . .
H10 H 0.0813 0.4180 -0.0139 0.048 Uiso 1 1 calc R U . . .
C11 C 0.2205(2) 0.52843(17) 0.10416(15) 0.0368(5) Uani 1 1 d . . . . .
H11 H 0.1629 0.5055 0.1487 0.044 Uiso 1 1 calc R U . . .
C12 C 0.35103(18) 0.61204(16) 0.13506(14) 0.0312(4) Uani 1 1 d . . . . .
H12 H 0.3838 0.6461 0.2012 0.037 Uiso 1 1 calc R U . . .
C13 C 0.43745(18) 0.64827(15) 0.07058(13) 0.0268(4) Uani 1 1 d . . . . .
C14 C 0.57516(18) 0.73502(15) 0.10211(12) 0.0251(4) Uani 1 1 d . . . . .
C15 C 0.87017(18) 0.81316(15) 0.15586(12) 0.0265(4) Uani 1 1 d . . . . .
C16 C 1.01435(19) 0.80794(17) 0.16441(14) 0.0315(4) Uani 1 1 d . . . . .
H16 H 1.0725 0.8327 0.1206 0.038 Uiso 1 1 calc R U . . .
C17 C 1.07283(19) 0.76636(17) 0.23733(14) 0.0336(4) Uani 1 1 d . . . . .
H17 H 1.1719 0.7636 0.2443 0.040 Uiso 1 1 calc R U . . .
C18 C 0.9878(2) 0.72902(16) 0.29983(13) 0.0328(4) Uani 1 1 d . . . . .
H18 H 1.0289 0.7008 0.3498 0.039 Uiso 1 1 calc R U . . .
C19 C 0.84269(19) 0.73215(15) 0.29069(12) 0.0276(4) Uani 1 1 d . . . . .
H19 H 0.7839 0.7045 0.3331 0.033 Uiso 1 1 calc R U . . .
C20 C 0.78468(18) 0.77611(15) 0.21905(12) 0.0240(4) Uani 1 1 d . . . . .
C21 C 0.81247(19) 0.97563(16) 0.09349(13) 0.0296(4) Uani 1 1 d . . . . .
C22 C 0.7177(2) 1.01621(19) 0.03667(14) 0.0407(5) Uani 1 1 d . . . . .
H22 H 0.6452 0.9604 -0.0121 0.049 Uiso 1 1 calc R U . . .
C23 C 0.7290(2) 1.13753(19) 0.05112(16) 0.0478(6) Uani 1 1 d . . . . .
H23 H 0.6640 1.1642 0.0118 0.057 Uiso 1 1 calc R U . . .
C24 C 0.8328(2) 1.22049(19) 0.12149(17) 0.0510(6) Uani 1 1 d . . . . .
H24 H 0.8399 1.3037 0.1310 0.061 Uiso 1 1 calc R U . . .
C25 C 0.9262(2) 1.1802(2) 0.17791(17) 0.0522(6) Uani 1 1 d . . . . .
H25 H 0.9980 1.2364 0.2269 0.063 Uiso 1 1 calc R U . . .
C26 C 0.9168(2) 1.05863(18) 0.16411(15) 0.0417(5) Uani 1 1 d . . . . .
H26 H 0.9824 1.0324 0.2034 0.050 Uiso 1 1 calc R U . . .
C27 C 0.58960(17) 0.87437(15) 0.25610(12) 0.0220(4) Uani 1 1 d . . . . .
C28 C 0.64882(17) 0.92337(15) 0.35194(12) 0.0241(4) Uani 1 1 d . . . . .
H28 H 0.7204 0.8923 0.3813 0.029 Uiso 1 1 calc R U . . .
C29 C 0.60427(17) 1.01657(15) 0.40435(12) 0.0244(4) Uani 1 1 d . . . . .
H29 H 0.6444 1.0479 0.4699 0.029 Uiso 1 1 calc R U . . .
C30 C 0.50192(17) 1.06550(15) 0.36331(12) 0.0245(4) Uani 1 1 d . . . . .
C31 C 0.44224(19) 1.01725(16) 0.26837(13) 0.0297(4) Uani 1 1 d . . . . .
H31 H 0.3718 1.0495 0.2391 0.036 Uiso 1 1 calc R U . . .
C32 C 0.48470(19) 0.92214(16) 0.21567(13) 0.0294(4) Uani 1 1 d . . . . .
H32 H 0.4415 0.8889 0.1508 0.035 Uiso 1 1 calc R U . . .
C33 C 0.57881(17) 1.26267(15) 0.47340(13) 0.0246(4) Uani 1 1 d . . . . .
C34 C 0.69329(18) 1.30577(16) 0.43043(14) 0.0298(4) Uani 1 1 d . . . . .
H34 H 0.6928 1.2712 0.3654 0.036 Uiso 1 1 calc R U . . .
C35 C 0.80840(19) 1.39940(17) 0.48248(14) 0.0334(4) Uani 1 1 d . . . . .
H35 H 0.8872 1.4282 0.4529 0.040 Uiso 1 1 calc R U . . .
C36 C 0.81046(19) 1.45158(16) 0.57663(14) 0.0312(4) Uani 1 1 d . . . . .
H36 H 0.8894 1.5166 0.6115 0.037 Uiso 1 1 calc R U . . .
C37 C 0.69721(19) 1.40860(16) 0.61943(13) 0.0321(4) Uani 1 1 d . . . . .
H37 H 0.6980 1.4439 0.6843 0.039 Uiso 1 1 calc R U . . .
C38 C 0.58155(19) 1.31398(16) 0.56854(13) 0.0304(4) Uani 1 1 d . . . . .
H38 H 0.5041 1.2843 0.5989 0.036 Uiso 1 1 calc R U . . .
C39 C 0.31578(18) 1.16211(16) 0.42583(12) 0.0244(4) Uani 1 1 d . . . . .
C40 C 0.27226(18) 1.26741(16) 0.45666(12) 0.0267(4) Uani 1 1 d . . . . .
H40 H 0.3420 1.3427 0.4730 0.032 Uiso 1 1 calc R U . . .
C41 C 0.12810(19) 1.26255(16) 0.46346(13) 0.0296(4) Uani 1 1 d . . . . .
H41 H 0.1006 1.3347 0.4862 0.036 Uiso 1 1 calc R U . . .
C42 C 0.02369(19) 1.15515(18) 0.43791(14) 0.0335(4) Uani 1 1 d . . . . .
H42 H -0.0752 1.1526 0.4422 0.040 Uiso 1 1 calc R U . . .
C43 C 0.06609(19) 1.05094(17) 0.40588(13) 0.0313(4) Uani 1 1 d . . . . .
H43 H -0.0049 0.9762 0.3875 0.038 Uiso 1 1 calc R U . . .
C44 C 0.21023(18) 1.05368(16) 0.40020(12) 0.0273(4) Uani 1 1 d . . . . .
H44 H 0.2372 0.9810 0.3787 0.033 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C21 1.427(2) . ?
N1 C1 1.440(2) . ?
N1 C15 1.441(2) . ?
N2 C27 1.422(2) . ?
N2 C14 1.434(2) . ?
N2 C20 1.440(2) . ?
N3 C39 1.408(2) . ?
N3 C33 1.423(2) . ?
N3 C30 1.433(2) . ?
C1 C14 1.350(2) . ?
C1 C2 1.435(2) . ?
C2 C3 1.411(3) . ?
C2 C7 1.412(3) . ?
C3 C4 1.370(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.391(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.363(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.411(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.451(3) . ?
C8 C9 1.416(3) . ?
C8 C13 1.417(2) . ?
C9 C10 1.361(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.394(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.367(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.404(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.433(2) . ?
C15 C20 1.386(2) . ?
C15 C16 1.386(2) . ?
C16 C17 1.384(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.376(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.388(2) . ?
C18 H18 0.9500 . ?
C19 C20 1.385(2) . ?
C19 H19 0.9500 . ?
C21 C26 1.382(3) . ?
C21 C22 1.393(3) . ?
C22 C23 1.382(3) . ?
C22 H22 0.9500 . ?
C23 C24 1.377(3) . ?
C23 H23 0.9500 . ?
C24 C25 1.379(3) . ?
C24 H24 0.9500 . ?
C25 C26 1.389(3) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
C27 C32 1.392(2) . ?
C27 C28 1.394(2) . ?
C28 C29 1.377(2) . ?
C28 H28 0.9500 . ?
C29 C30 1.387(2) . ?
C29 H29 0.9500 . ?
C30 C31 1.382(2) . ?
C31 C32 1.385(2) . ?
C31 H31 0.9500 . ?
C32 H32 0.9500 . ?
C33 C34 1.384(2) . ?
C33 C38 1.388(2) . ?
C34 C35 1.383(2) . ?
C34 H34 0.9500 . ?
C35 C36 1.379(3) . ?
C35 H35 0.9500 . ?
C36 C37 1.373(2) . ?
C36 H36 0.9500 . ?
C37 C38 1.388(2) . ?
C37 H37 0.9500 . ?
C38 H38 0.9500 . ?
C39 C44 1.391(2) . ?
C39 C40 1.398(2) . ?
C40 C41 1.384(2) . ?
C40 H40 0.9500 . ?
C41 C42 1.377(3) . ?
C41 H41 0.9500 . ?
C42 C43 1.384(3) . ?
C42 H42 0.9500 . ?
C43 C44 1.385(2) . ?
C43 H43 0.9500 . ?
C44 H44 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C21 N1 C1 117.48(14) . . ?
C21 N1 C15 116.92(14) . . ?
C1 N1 C15 109.93(14) . . ?
C27 N2 C14 118.45(14) . . ?
C27 N2 C20 118.41(13) . . ?
C14 N2 C20 110.80(13) . . ?
C39 N3 C33 122.09(14) . . ?
C39 N3 C30 121.33(14) . . ?
C33 N3 C30 116.43(13) . . ?
C14 C1 C2 121.05(17) . . ?
C14 C1 N1 117.69(15) . . ?
C2 C1 N1 120.98(16) . . ?
C3 C2 C7 120.16(17) . . ?
C3 C2 C1 120.82(18) . . ?
C7 C2 C1 119.01(17) . . ?
C4 C3 C2 120.1(2) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C3 C4 C5 120.1(2) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C6 C5 C4 120.8(2) . . ?
C6 C5 H5 119.6 . . ?
C4 C5 H5 119.6 . . ?
C5 C6 C7 121.2(2) . . ?
C5 C6 H6 119.4 . . ?
C7 C6 H6 119.4 . . ?
C2 C7 C6 117.65(19) . . ?
C2 C7 C8 119.97(16) . . ?
C6 C7 C8 122.38(19) . . ?
C9 C8 C13 117.37(18) . . ?
C9 C8 C7 123.45(17) . . ?
C13 C8 C7 119.16(17) . . ?
C10 C9 C8 121.97(18) . . ?
C10 C9 H9 119.0 . . ?
C8 C9 H9 119.0 . . ?
C9 C10 C11 119.96(18) . . ?
C9 C10 H10 120.0 . . ?
C11 C10 H10 120.0 . . ?
C12 C11 C10 120.13(19) . . ?
C12 C11 H11 119.9 . . ?
C10 C11 H11 119.9 . . ?
C11 C12 C13 121.02(18) . . ?
C11 C12 H12 119.5 . . ?
C13 C12 H12 119.5 . . ?
C12 C13 C8 119.53(17) . . ?
C12 C13 C14 121.56(16) . . ?
C8 C13 C14 118.91(17) . . ?
C1 C14 C13 121.88(16) . . ?
C1 C14 N2 118.09(15) . . ?
C13 C14 N2 119.70(15) . . ?
C20 C15 C16 120.48(17) . . ?
C20 C15 N1 117.17(15) . . ?
C16 C15 N1 122.27(16) . . ?
C17 C16 C15 119.36(18) . . ?
C17 C16 H16 120.3 . . ?
C15 C16 H16 120.3 . . ?
C18 C17 C16 120.19(17) . . ?
C18 C17 H17 119.9 . . ?
C16 C17 H17 119.9 . . ?
C17 C18 C19 120.72(17) . . ?
C17 C18 H18 119.6 . . ?
C19 C18 H18 119.6 . . ?
C20 C19 C18 119.24(17) . . ?
C20 C19 H19 120.4 . . ?
C18 C19 H19 120.4 . . ?
C15 C20 C19 119.99(16) . . ?
C15 C20 N2 116.84(15) . . ?
C19 C20 N2 123.00(16) . . ?
C26 C21 C22 118.81(18) . . ?
C26 C21 N1 120.85(17) . . ?
C22 C21 N1 120.34(17) . . ?
C23 C22 C21 120.1(2) . . ?
C23 C22 H22 119.9 . . ?
C21 C22 H22 119.9 . . ?
C24 C23 C22 121.2(2) . . ?
C24 C23 H23 119.4 . . ?
C22 C23 H23 119.4 . . ?
C23 C24 C25 118.6(2) . . ?
C23 C24 H24 120.7 . . ?
C25 C24 H24 120.7 . . ?
C24 C25 C26 121.0(2) . . ?
C24 C25 H25 119.5 . . ?
C26 C25 H25 119.5 . . ?
C21 C26 C25 120.28(19) . . ?
C21 C26 H26 119.9 . . ?
C25 C26 H26 119.9 . . ?
C32 C27 C28 118.08(16) . . ?
C32 C27 N2 121.00(15) . . ?
C28 C27 N2 120.92(15) . . ?
C29 C28 C27 120.44(16) . . ?
C29 C28 H28 119.8 . . ?
C27 C28 H28 119.8 . . ?
C28 C29 C30 121.27(16) . . ?
C28 C29 H29 119.4 . . ?
C30 C29 H29 119.4 . . ?
C31 C30 C29 118.69(16) . . ?
C31 C30 N3 121.79(16) . . ?
C29 C30 N3 119.52(15) . . ?
C30 C31 C32 120.32(17) . . ?
C30 C31 H31 119.8 . . ?
C32 C31 H31 119.8 . . ?
C31 C32 C27 121.17(16) . . ?
C31 C32 H32 119.4 . . ?
C27 C32 H32 119.4 . . ?
C34 C33 C38 119.34(16) . . ?
C34 C33 N3 119.22(16) . . ?
C38 C33 N3 121.43(16) . . ?
C33 C34 C35 119.76(18) . . ?
C33 C34 H34 120.1 . . ?
C35 C34 H34 120.1 . . ?
C36 C35 C34 121.01(17) . . ?
C36 C35 H35 119.5 . . ?
C34 C35 H35 119.5 . . ?
C37 C36 C35 119.27(17) . . ?
C37 C36 H36 120.4 . . ?
C35 C36 H36 120.4 . . ?
C36 C37 C38 120.48(18) . . ?
C36 C37 H37 119.8 . . ?
C38 C37 H37 119.8 . . ?
C33 C38 C37 120.11(17) . . ?
C33 C38 H38 119.9 . . ?
C37 C38 H38 119.9 . . ?
C44 C39 C40 118.32(16) . . ?
C44 C39 N3 120.48(16) . . ?
C40 C39 N3 121.19(15) . . ?
C41 C40 C39 120.33(16) . . ?
C41 C40 H40 119.8 . . ?
C39 C40 H40 119.8 . . ?
C42 C41 C40 121.26(17) . . ?
C42 C41 H41 119.4 . . ?
C40 C41 H41 119.4 . . ?
C41 C42 C43 118.51(17) . . ?
C41 C42 H42 120.7 . . ?
C43 C42 H42 120.7 . . ?
C42 C43 C44 121.12(17) . . ?
C42 C43 H43 119.4 . . ?
C44 C43 H43 119.4 . . ?
C43 C44 C39 120.44(17) . . ?
C43 C44 H44 119.8 . . ?
C39 C44 H44 119.8 . . ?

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
C21 N1 C1 C14 -93.83(19) . . . . ?
C15 N1 C1 C14 43.2(2) . . . . ?
C21 N1 C1 C2 92.2(2) . . . . ?
C15 N1 C1 C2 -130.77(17) . . . . ?
C14 C1 C2 C3 -177.52(16) . . . . ?
N1 C1 C2 C3 -3.8(3) . . . . ?
C14 C1 C2 C7 1.8(3) . . . . ?
N1 C1 C2 C7 175.56(15) . . . . ?
C7 C2 C3 C4 1.0(3) . . . . ?
C1 C2 C3 C4 -179.64(18) . . . . ?
C2 C3 C4 C5 -0.2(3) . . . . ?
C3 C4 C5 C6 -0.4(3) . . . . ?
C4 C5 C6 C7 0.3(3) . . . . ?
C3 C2 C7 C6 -1.1(3) . . . . ?
C1 C2 C7 C6 179.51(17) . . . . ?
C3 C2 C7 C8 178.10(16) . . . . ?
C1 C2 C7 C8 -1.2(2) . . . . ?
C5 C6 C7 C2 0.5(3) . . . . ?
C5 C6 C7 C8 -178.71(18) . . . . ?
C2 C7 C8 C9 -178.11(17) . . . . ?
C6 C7 C8 C9 1.1(3) . . . . ?
C2 C7 C8 C13 0.2(2) . . . . ?
C6 C7 C8 C13 179.41(17) . . . . ?
C13 C8 C9 C10 0.8(3) . . . . ?
C7 C8 C9 C10 179.12(17) . . . . ?
C8 C9 C10 C11 -0.1(3) . . . . ?
C9 C10 C11 C12 -0.6(3) . . . . ?
C10 C11 C12 C13 0.6(3) . . . . ?
C11 C12 C13 C8 0.1(3) . . . . ?
C11 C12 C13 C14 -179.42(17) . . . . ?
C9 C8 C13 C12 -0.8(2) . . . . ?
C7 C8 C13 C12 -179.17(16) . . . . ?
C9 C8 C13 C14 178.74(15) . . . . ?
C7 C8 C13 C14 0.3(2) . . . . ?
C2 C1 C14 C13 -1.3(3) . . . . ?
N1 C1 C14 C13 -175.26(15) . . . . ?
C2 C1 C14 N2 172.14(15) . . . . ?
N1 C1 C14 N2 -1.8(2) . . . . ?
C12 C13 C14 C1 179.72(16) . . . . ?
C8 C13 C14 C1 0.2(2) . . . . ?
C12 C13 C14 N2 6.4(2) . . . . ?
C8 C13 C14 N2 -173.12(15) . . . . ?
C27 N2 C14 C1 101.11(18) . . . . ?
C20 N2 C14 C1 -40.6(2) . . . . ?
C27 N2 C14 C13 -85.28(19) . . . . ?
C20 N2 C14 C13 133.03(16) . . . . ?
C21 N1 C15 C20 95.15(19) . . . . ?
C1 N1 C15 C20 -42.1(2) . . . . ?
C21 N1 C15 C16 -88.2(2) . . . . ?
C1 N1 C15 C16 134.56(17) . . . . ?
C20 C15 C16 C17 -0.6(3) . . . . ?
N1 C15 C16 C17 -177.18(16) . . . . ?
C15 C16 C17 C18 0.9(3) . . . . ?
C16 C17 C18 C19 0.2(3) . . . . ?
C17 C18 C19 C20 -1.5(3) . . . . ?
C16 C15 C20 C19 -0.8(3) . . . . ?
N1 C15 C20 C19 175.97(15) . . . . ?
C16 C15 C20 N2 -176.22(16) . . . . ?
N1 C15 C20 N2 0.5(2) . . . . ?
C18 C19 C20 C15 1.8(3) . . . . ?
C18 C19 C20 N2 176.99(16) . . . . ?
C27 N2 C20 C15 -100.89(18) . . . . ?
C14 N2 C20 C15 40.8(2) . . . . ?
C27 N2 C20 C19 83.8(2) . . . . ?
C14 N2 C20 C19 -134.49(17) . . . . ?
C1 N1 C21 C26 151.29(18) . . . . ?
C15 N1 C21 C26 17.3(2) . . . . ?
C1 N1 C21 C22 -28.1(2) . . . . ?
C15 N1 C21 C22 -162.11(17) . . . . ?
C26 C21 C22 C23 0.2(3) . . . . ?
N1 C21 C22 C23 179.55(18) . . . . ?
C21 C22 C23 C24 -0.2(3) . . . . ?
C22 C23 C24 C25 0.0(4) . . . . ?
C23 C24 C25 C26 0.3(4) . . . . ?
C22 C21 C26 C25 0.1(3) . . . . ?
N1 C21 C26 C25 -179.26(19) . . . . ?
C24 C25 C26 C21 -0.4(3) . . . . ?
C14 N2 C27 C32 4.1(2) . . . . ?
C20 N2 C27 C32 142.90(16) . . . . ?
C14 N2 C27 C28 -176.64(15) . . . . ?
C20 N2 C27 C28 -37.9(2) . . . . ?
C32 C27 C28 C29 -0.2(2) . . . . ?
N2 C27 C28 C29 -179.45(15) . . . . ?
C27 C28 C29 C30 -1.2(3) . . . . ?
C28 C29 C30 C31 1.3(3) . . . . ?
C28 C29 C30 N3 -177.86(15) . . . . ?
C39 N3 C30 C31 54.4(2) . . . . ?
C33 N3 C30 C31 -129.86(18) . . . . ?
C39 N3 C30 C29 -126.41(17) . . . . ?
C33 N3 C30 C29 49.3(2) . . . . ?
C29 C30 C31 C32 -0.2(3) . . . . ?
N3 C30 C31 C32 178.98(16) . . . . ?
C30 C31 C32 C27 -1.1(3) . . . . ?
C28 C27 C32 C31 1.3(3) . . . . ?
N2 C27 C32 C31 -179.41(16) . . . . ?
C39 N3 C33 C34 -137.93(17) . . . . ?
C30 N3 C33 C34 46.4(2) . . . . ?
C39 N3 C33 C38 43.4(2) . . . . ?
C30 N3 C33 C38 -132.32(18) . . . . ?
C38 C33 C34 C35 -0.2(3) . . . . ?
N3 C33 C34 C35 -178.97(16) . . . . ?
C33 C34 C35 C36 -0.6(3) . . . . ?
C34 C35 C36 C37 0.9(3) . . . . ?
C35 C36 C37 C38 -0.2(3) . . . . ?
C34 C33 C38 C37 0.9(3) . . . . ?
N3 C33 C38 C37 179.57(16) . . . . ?
C36 C37 C38 C33 -0.6(3) . . . . ?
C33 N3 C39 C44 -157.70(16) . . . . ?
C30 N3 C39 C44 17.8(3) . . . . ?
C33 N3 C39 C40 23.1(3) . . . . ?
C30 N3 C39 C40 -161.40(16) . . . . ?
C44 C39 C40 C41 1.6(3) . . . . ?
N3 C39 C40 C41 -179.22(16) . . . . ?
C39 C40 C41 C42 -1.7(3) . . . . ?
C40 C41 C42 C43 0.6(3) . . . . ?
C41 C42 C43 C44 0.6(3) . . . . ?
C42 C43 C44 C39 -0.7(3) . . . . ?
C40 C39 C44 C43 -0.4(3) . . . . ?
N3 C39 C44 C43 -179.61(16) . . . . ?

_refine_diff_density_max         0.247
_refine_diff_density_min         -0.256
_refine_diff_density_rms         0.051

_shelxl_version_number           2013-4

_database_code_depnum_ccdc_archive 'CCDC 992518'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_mo_dm14097_0m

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C45 H31 Cl N3'
_chemical_formula_weight         649.18

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'
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                   9.322(5)
_cell_length_b                   12.934(7)
_cell_length_c                   14.662(8)
_cell_angle_alpha                75.264(9)
_cell_angle_beta                 81.913(10)
_cell_angle_gamma                71.406(11)
_cell_volume                     1616.9(16)
_cell_formula_units_Z            2
_cell_measurement_temperature    140(2)
_cell_measurement_reflns_used    994
_cell_measurement_theta_min      2.31
_cell_measurement_theta_max      22.68

_exptl_crystal_description       ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.333
_exptl_crystal_F_000             678
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    0.158
_shelx_estimated_absorpt_T_min   0.969
_shelx_estimated_absorpt_T_max   0.977
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5680
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      140(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11776
_diffrn_reflns_av_unetI/netI     0.1618
_diffrn_reflns_av_R_equivalents  0.0857
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.704
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_full        25.242
_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             6345
_reflns_number_gt                2861
_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    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_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)+(0.0911P)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         6345
_refine_ls_number_parameters     442
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1697
_refine_ls_R_factor_gt           0.0729
_refine_ls_wR_factor_ref         0.2258
_refine_ls_wR_factor_gt          0.1722
_refine_ls_goodness_of_fit_ref   0.962
_refine_ls_restrained_S_all      0.962
_refine_ls_shift/su_max          0.006
_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 0.0635(4) -0.0157(3) 0.2574(2) 0.0312(9) Uani 1 1 d . . . . .
N2 N 0.2805(4) 0.0834(3) 0.2611(2) 0.0296(8) Uani 1 1 d . . . . .
N3 N 0.2313(4) 0.3941(3) -0.0892(2) 0.0321(9) Uani 1 1 d . . . . .
C1 C 0.0349(5) 0.0583(3) 0.3198(3) 0.0254(9) Uani 1 1 d . . . . .
C2 C 0.1451(5) 0.1035(3) 0.3255(3) 0.0279(10) Uani 1 1 d . . . . .
C3 C 0.1361(5) 0.1665(3) 0.3952(3) 0.0276(9) Uani 1 1 d . . . . .
C4 C 0.2521(5) 0.2102(3) 0.4028(3) 0.0344(11) Uani 1 1 d . . . . .
H4 H 0.3403 0.1981 0.3610 0.041 Uiso 1 1 calc R U . . .
C5 C 0.2405(5) 0.2701(3) 0.4697(3) 0.0395(11) Uani 1 1 d . . . . .
H5 H 0.3193 0.3005 0.4733 0.047 Uiso 1 1 calc R U . . .
C6 C 0.1128(5) 0.2861(4) 0.5324(3) 0.0407(12) Uani 1 1 d . . . . .
H6 H 0.1055 0.3263 0.5797 0.049 Uiso 1 1 calc R U . . .
C7 C -0.0024(5) 0.2444(3) 0.5263(3) 0.0348(11) Uani 1 1 d . . . . .
H7 H -0.0887 0.2564 0.5697 0.042 Uiso 1 1 calc R U . . .
C8 C 0.0032(5) 0.1842(3) 0.4577(3) 0.0290(10) Uani 1 1 d . . . . .
C9 C -0.1192(5) 0.1417(3) 0.4476(3) 0.0277(10) Uani 1 1 d . . . . .
C10 C -0.2562(5) 0.1610(3) 0.5042(3) 0.0338(11) Uani 1 1 d . . . . .
H10 H -0.2704 0.2041 0.5503 0.041 Uiso 1 1 calc R U . . .
C11 C -0.3694(5) 0.1189(3) 0.4943(3) 0.0349(11) Uani 1 1 d . . . . .
H11 H -0.4616 0.1344 0.5323 0.042 Uiso 1 1 calc R U . . .
C12 C -0.3501(5) 0.0537(3) 0.4290(3) 0.0361(11) Uani 1 1 d . . . . .
H12 H -0.4289 0.0247 0.4228 0.043 Uiso 1 1 calc R U . . .
C13 C -0.2182(5) 0.0311(3) 0.3738(3) 0.0332(10) Uani 1 1 d . . . . .
H13 H -0.2045 -0.0155 0.3306 0.040 Uiso 1 1 calc R U . . .
C14 C -0.1023(5) 0.0765(3) 0.3802(3) 0.0261(9) Uani 1 1 d . . . . .
C15 C 0.2184(5) -0.0808(3) 0.2495(3) 0.0287(10) Uani 1 1 d . . . . .
C16 C 0.3296(5) -0.0325(3) 0.2551(3) 0.0309(10) Uani 1 1 d . . . . .
C17 C 0.4812(5) -0.0938(4) 0.2559(3) 0.0371(11) Uani 1 1 d . . . . .
H17 H 0.5557 -0.0599 0.2606 0.044 Uiso 1 1 calc R U . . .
C18 C 0.5247(6) -0.2060(4) 0.2496(3) 0.0424(12) Uani 1 1 d . . . . .
H18 H 0.6287 -0.2485 0.2488 0.051 Uiso 1 1 calc R U . . .
C19 C 0.4143(6) -0.2538(4) 0.2447(3) 0.0403(12) Uani 1 1 d . . . . .
H19 H 0.4429 -0.3299 0.2404 0.048 Uiso 1 1 calc R U . . .
C20 C 0.2629(5) -0.1932(3) 0.2460(3) 0.0369(11) Uani 1 1 d . . . . .
H20 H 0.1884 -0.2284 0.2445 0.044 Uiso 1 1 calc R U . . .
C21 C -0.0344(5) 0.0137(4) 0.1817(3) 0.0339(10) Uani 1 1 d . . . . .
C22 C -0.0603(5) -0.0679(4) 0.1462(3) 0.0471(13) Uani 1 1 d . . . . .
H22 H -0.0125 -0.1447 0.1721 0.057 Uiso 1 1 calc R U . . .
C23 C -0.1548(6) -0.0386(5) 0.0738(4) 0.0607(15) Uani 1 1 d . . . . .
H23 H -0.1687 -0.0956 0.0489 0.073 Uiso 1 1 calc R U . . .
C24 C -0.2297(6) 0.0720(5) 0.0366(4) 0.0540(14) Uani 1 1 d . . . . .
H24 H -0.2950 0.0916 -0.0133 0.065 Uiso 1 1 calc R U . . .
C25 C -0.2077(6) 0.1540(5) 0.0736(3) 0.0537(14) Uani 1 1 d . . . . .
H25 H -0.2592 0.2305 0.0493 0.064 Uiso 1 1 calc R U . . .
C26 C -0.1101(5) 0.1247(4) 0.1466(3) 0.0425(12) Uani 1 1 d . . . . .
H26 H -0.0960 0.1813 0.1718 0.051 Uiso 1 1 calc R U . . .
C27 C 0.2750(5) 0.1635(3) 0.1743(3) 0.0274(10) Uani 1 1 d . . . . .
C28 C 0.1705(5) 0.2699(3) 0.1650(3) 0.0382(11) Uani 1 1 d . . . . .
H28 H 0.1057 0.2897 0.2179 0.046 Uiso 1 1 calc R U . . .
C29 C 0.1607(5) 0.3467(3) 0.0790(3) 0.0386(11) Uani 1 1 d . . . . .
H29 H 0.0895 0.4190 0.0734 0.046 Uiso 1 1 calc R U . . .
C30 C 0.2539(5) 0.3187(3) 0.0014(3) 0.0320(10) Uani 1 1 d . . . . .
C31 C 0.3611(5) 0.2150(4) 0.0102(3) 0.0391(11) Uani 1 1 d . . . . .
H31 H 0.4271 0.1963 -0.0426 0.047 Uiso 1 1 calc R U . . .
C32 C 0.3720(5) 0.1387(4) 0.0957(3) 0.0381(11) Uani 1 1 d . . . . .
H32 H 0.4468 0.0679 0.1013 0.046 Uiso 1 1 calc R U . . .
C33 C 0.3167(5) 0.4658(3) -0.1345(3) 0.0315(10) Uani 1 1 d . . . . .
C34 C 0.4414(5) 0.4818(4) -0.1056(3) 0.0382(11) Uani 1 1 d . . . . .
H34 H 0.4842 0.4391 -0.0476 0.046 Uiso 1 1 calc R U . . .
C35 C 0.5017(6) 0.5616(4) -0.1637(4) 0.0497(13) Uani 1 1 d . . . . .
H35 H 0.5873 0.5741 -0.1451 0.060 Uiso 1 1 calc R U . . .
C36 C 0.4412(6) 0.6242(4) -0.2485(4) 0.0579(15) Uani 1 1 d . . . . .
H36 H 0.4845 0.6794 -0.2867 0.070 Uiso 1 1 calc R U . . .
C37 C 0.3184(6) 0.6068(4) -0.2779(3) 0.0502(14) Uani 1 1 d . . . . .
H37 H 0.2776 0.6494 -0.3364 0.060 Uiso 1 1 calc R U . . .
C38 C 0.2545(5) 0.5265(3) -0.2212(3) 0.0354(11) Uani 1 1 d . . . . .
C39 C 0.1253(5) 0.4889(3) -0.2279(3) 0.0340(11) Uani 1 1 d . . . . .
C40 C 0.0164(6) 0.5195(4) -0.2943(3) 0.0438(12) Uani 1 1 d . . . . .
H40 H 0.0241 0.5715 -0.3522 0.053 Uiso 1 1 calc R U . . .
C41 C -0.1022(6) 0.4734(4) -0.2749(4) 0.0521(14) Uani 1 1 d . . . . .
H41 H -0.1767 0.4936 -0.3194 0.063 Uiso 1 1 calc R U . . .
C42 C -0.1126(6) 0.3965(4) -0.1891(4) 0.0509(14) Uani 1 1 d . . . . .
H42 H -0.1963 0.3670 -0.1757 0.061 Uiso 1 1 calc R U . . .
C43 C -0.0041(5) 0.3626(4) -0.1235(4) 0.0429(12) Uani 1 1 d . . . . .
H43 H -0.0105 0.3090 -0.0663 0.051 Uiso 1 1 calc R U . . .
C44 C 0.1137(5) 0.4096(3) -0.1442(3) 0.0324(10) Uani 1 1 d . . . . .
Cl1 Cl 0.3385(2) 0.52307(17) 0.48722(18) 0.1065(8) Uani 1 1 d . . . . .
C1S C 0.525(2) 0.5554(9) 0.4681(11) 0.247(8) Uani 1 1 d . . . . .
H1SA H 0.5266 0.5670 0.3986 0.296 Uiso 1 1 calc R U . . .
H1SB H 0.4810 0.6256 0.4907 0.296 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C15 1.427(5) . ?
N1 C1 1.428(5) . ?
N1 C21 1.433(5) . ?
N2 C27 1.419(5) . ?
N2 C16 1.442(5) . ?
N2 C2 1.460(5) . ?
N3 C44 1.385(5) . ?
N3 C33 1.394(6) . ?
N3 C30 1.432(5) . ?
C1 C2 1.355(6) . ?
C1 C14 1.438(5) . ?
C2 C3 1.440(5) . ?
C3 C4 1.398(6) . ?
C3 C8 1.426(6) . ?
C4 C5 1.370(6) . ?
C4 H4 0.9500 . ?
C5 C6 1.392(7) . ?
C5 H5 0.9500 . ?
C6 C7 1.369(6) . ?
C6 H6 0.9500 . ?
C7 C8 1.406(5) . ?
C7 H7 0.9500 . ?
C8 C9 1.455(6) . ?
C9 C10 1.409(6) . ?
C9 C14 1.418(5) . ?
C10 C11 1.372(6) . ?
C10 H10 0.9500 . ?
C11 C12 1.387(6) . ?
C11 H11 0.9500 . ?
C12 C13 1.366(6) . ?
C12 H12 0.9500 . ?
C13 C14 1.407(6) . ?
C13 H13 0.9500 . ?
C15 C20 1.390(5) . ?
C15 C16 1.391(6) . ?
C16 C17 1.383(6) . ?
C17 C18 1.400(6) . ?
C17 H17 0.9500 . ?
C18 C19 1.377(7) . ?
C18 H18 0.9500 . ?
C19 C20 1.379(6) . ?
C19 H19 0.9500 . ?
C20 H20 0.9500 . ?
C21 C26 1.380(6) . ?
C21 C22 1.387(6) . ?
C22 C23 1.376(6) . ?
C22 H22 0.9500 . ?
C23 C24 1.381(7) . ?
C23 H23 0.9500 . ?
C24 C25 1.387(7) . ?
C24 H24 0.9500 . ?
C25 C26 1.402(6) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
C27 C28 1.395(5) . ?
C27 C32 1.400(6) . ?
C28 C29 1.386(6) . ?
C28 H28 0.9500 . ?
C29 C30 1.383(6) . ?
C29 H29 0.9500 . ?
C30 C31 1.381(6) . ?
C31 C32 1.377(6) . ?
C31 H31 0.9500 . ?
C32 H32 0.9500 . ?
C33 C34 1.382(6) . ?
C33 C38 1.405(6) . ?
C34 C35 1.377(6) . ?
C34 H34 0.9500 . ?
C35 C36 1.383(7) . ?
C35 H35 0.9500 . ?
C36 C37 1.377(7) . ?
C36 H36 0.9500 . ?
C37 C38 1.394(7) . ?
C37 H37 0.9500 . ?
C38 C39 1.459(6) . ?
C39 C40 1.400(6) . ?
C39 C44 1.401(6) . ?
C40 C41 1.380(7) . ?
C40 H40 0.9500 . ?
C41 C42 1.403(7) . ?
C41 H41 0.9500 . ?
C42 C43 1.385(6) . ?
C42 H42 0.9500 . ?
C43 C44 1.381(6) . ?
C43 H43 0.9500 . ?
Cl1 C1S 1.466(14) 2_666 ?
Cl1 C1S 1.884(16) . ?
C1S Cl1 1.466(14) 2_666 ?
C1S C1S 1.66(2) 2_666 ?
C1S H1SA 0.9900 . ?
C1S H1SB 0.9900 . ?

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
C15 N1 C1 113.7(3) . . ?
C15 N1 C21 121.7(3) . . ?
C1 N1 C21 118.5(3) . . ?
C27 N2 C16 116.3(3) . . ?
C27 N2 C2 115.9(3) . . ?
C16 N2 C2 109.4(3) . . ?
C44 N3 C33 109.2(3) . . ?
C44 N3 C30 123.9(4) . . ?
C33 N3 C30 126.8(4) . . ?
C2 C1 N1 118.1(4) . . ?
C2 C1 C14 121.4(4) . . ?
N1 C1 C14 120.3(4) . . ?
C1 C2 C3 122.3(4) . . ?
C1 C2 N2 118.7(4) . . ?
C3 C2 N2 118.9(4) . . ?
C4 C3 C8 119.9(4) . . ?
C4 C3 C2 122.3(4) . . ?
C8 C3 C2 117.9(4) . . ?
C5 C4 C3 121.1(4) . . ?
C5 C4 H4 119.5 . . ?
C3 C4 H4 119.5 . . ?
C4 C5 C6 119.7(4) . . ?
C4 C5 H5 120.2 . . ?
C6 C5 H5 120.2 . . ?
C7 C6 C5 120.4(4) . . ?
C7 C6 H6 119.8 . . ?
C5 C6 H6 119.8 . . ?
C6 C7 C8 121.9(4) . . ?
C6 C7 H7 119.0 . . ?
C8 C7 H7 119.0 . . ?
C7 C8 C3 117.1(4) . . ?
C7 C8 C9 123.2(4) . . ?
C3 C8 C9 119.7(4) . . ?
C10 C9 C14 117.5(4) . . ?
C10 C9 C8 122.4(4) . . ?
C14 C9 C8 120.1(4) . . ?
C11 C10 C9 121.4(4) . . ?
C11 C10 H10 119.3 . . ?
C9 C10 H10 119.3 . . ?
C10 C11 C12 120.4(4) . . ?
C10 C11 H11 119.8 . . ?
C12 C11 H11 119.8 . . ?
C13 C12 C11 120.3(4) . . ?
C13 C12 H12 119.9 . . ?
C11 C12 H12 119.9 . . ?
C12 C13 C14 120.5(4) . . ?
C12 C13 H13 119.8 . . ?
C14 C13 H13 119.8 . . ?
C13 C14 C9 119.9(4) . . ?
C13 C14 C1 121.7(4) . . ?
C9 C14 C1 118.4(4) . . ?
C20 C15 C16 118.5(4) . . ?
C20 C15 N1 123.2(4) . . ?
C16 C15 N1 118.0(3) . . ?
C17 C16 C15 121.0(4) . . ?
C17 C16 N2 121.4(4) . . ?
C15 C16 N2 117.5(4) . . ?
C16 C17 C18 119.8(5) . . ?
C16 C17 H17 120.1 . . ?
C18 C17 H17 120.1 . . ?
C19 C18 C17 118.9(4) . . ?
C19 C18 H18 120.5 . . ?
C17 C18 H18 120.5 . . ?
C18 C19 C20 121.1(4) . . ?
C18 C19 H19 119.4 . . ?
C20 C19 H19 119.4 . . ?
C19 C20 C15 120.6(4) . . ?
C19 C20 H20 119.7 . . ?
C15 C20 H20 119.7 . . ?
C26 C21 C22 119.1(4) . . ?
C26 C21 N1 119.7(4) . . ?
C22 C21 N1 121.1(4) . . ?
C23 C22 C21 120.6(5) . . ?
C23 C22 H22 119.7 . . ?
C21 C22 H22 119.7 . . ?
C22 C23 C24 121.1(5) . . ?
C22 C23 H23 119.4 . . ?
C24 C23 H23 119.4 . . ?
C23 C24 C25 118.7(5) . . ?
C23 C24 H24 120.7 . . ?
C25 C24 H24 120.7 . . ?
C24 C25 C26 120.4(5) . . ?
C24 C25 H25 119.8 . . ?
C26 C25 H25 119.8 . . ?
C21 C26 C25 120.0(5) . . ?
C21 C26 H26 120.0 . . ?
C25 C26 H26 120.0 . . ?
C28 C27 C32 118.1(4) . . ?
C28 C27 N2 120.3(4) . . ?
C32 C27 N2 121.5(3) . . ?
C29 C28 C27 120.4(4) . . ?
C29 C28 H28 119.8 . . ?
C27 C28 H28 119.8 . . ?
C30 C29 C28 120.4(4) . . ?
C30 C29 H29 119.8 . . ?
C28 C29 H29 119.8 . . ?
C31 C30 C29 119.9(4) . . ?
C31 C30 N3 120.2(4) . . ?
C29 C30 N3 119.8(4) . . ?
C32 C31 C30 119.9(4) . . ?
C32 C31 H31 120.1 . . ?
C30 C31 H31 120.1 . . ?
C31 C32 C27 121.2(4) . . ?
C31 C32 H32 119.4 . . ?
C27 C32 H32 119.4 . . ?
C34 C33 N3 129.9(4) . . ?
C34 C33 C38 121.7(4) . . ?
N3 C33 C38 108.4(4) . . ?
C35 C34 C33 117.8(4) . . ?
C35 C34 H34 121.1 . . ?
C33 C34 H34 121.1 . . ?
C34 C35 C36 121.8(5) . . ?
C34 C35 H35 119.1 . . ?
C36 C35 H35 119.1 . . ?
C37 C36 C35 120.3(5) . . ?
C37 C36 H36 119.8 . . ?
C35 C36 H36 119.8 . . ?
C36 C37 C38 119.6(4) . . ?
C36 C37 H37 120.2 . . ?
C38 C37 H37 120.2 . . ?
C37 C38 C33 118.8(5) . . ?
C37 C38 C39 134.4(4) . . ?
C33 C38 C39 106.7(4) . . ?
C40 C39 C44 119.1(4) . . ?
C40 C39 C38 134.1(4) . . ?
C44 C39 C38 106.7(4) . . ?
C41 C40 C39 119.5(5) . . ?
C41 C40 H40 120.3 . . ?
C39 C40 H40 120.3 . . ?
C40 C41 C42 119.9(4) . . ?
C40 C41 H41 120.1 . . ?
C42 C41 H41 120.1 . . ?
C43 C42 C41 121.8(5) . . ?
C43 C42 H42 119.1 . . ?
C41 C42 H42 119.1 . . ?
C44 C43 C42 117.5(5) . . ?
C44 C43 H43 121.3 . . ?
C42 C43 H43 121.3 . . ?
C43 C44 N3 128.8(4) . . ?
C43 C44 C39 122.3(4) . . ?
N3 C44 C39 108.9(4) . . ?
C1S Cl1 C1S 58.0(7) 2_666 . ?
Cl1 C1S C1S 73.7(8) 2_666 2_666 ?
Cl1 C1S Cl1 122.0(7) 2_666 . ?
C1S C1S Cl1 48.3(9) 2_666 . ?
Cl1 C1S H1SA 116.2 2_666 . ?
C1S C1S H1SA 116.2 2_666 . ?
Cl1 C1S H1SA 92.7 . . ?
Cl1 C1S H1SB 116.2 2_666 . ?
C1S C1S H1SB 116.2 2_666 . ?
Cl1 C1S H1SB 92.7 . . ?
H1SA C1S H1SB 113.1 . . ?

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
C15 N1 C1 C2 33.3(5) . . . . ?
C21 N1 C1 C2 -119.6(4) . . . . ?
C15 N1 C1 C14 -141.8(4) . . . . ?
C21 N1 C1 C14 65.3(5) . . . . ?
N1 C1 C2 C3 -171.4(3) . . . . ?
C14 C1 C2 C3 3.6(6) . . . . ?
N1 C1 C2 N2 6.0(5) . . . . ?
C14 C1 C2 N2 -179.0(3) . . . . ?
C27 N2 C2 C1 90.9(4) . . . . ?
C16 N2 C2 C1 -43.0(5) . . . . ?
C27 N2 C2 C3 -91.7(4) . . . . ?
C16 N2 C2 C3 134.4(4) . . . . ?
C1 C2 C3 C4 178.0(4) . . . . ?
N2 C2 C3 C4 0.7(5) . . . . ?
C1 C2 C3 C8 -2.2(5) . . . . ?
N2 C2 C3 C8 -179.5(3) . . . . ?
C8 C3 C4 C5 0.0(6) . . . . ?
C2 C3 C4 C5 179.9(4) . . . . ?
C3 C4 C5 C6 1.2(6) . . . . ?
C4 C5 C6 C7 -1.3(6) . . . . ?
C5 C6 C7 C8 0.1(6) . . . . ?
C6 C7 C8 C3 1.1(6) . . . . ?
C6 C7 C8 C9 -178.1(4) . . . . ?
C4 C3 C8 C7 -1.2(5) . . . . ?
C2 C3 C8 C7 179.0(3) . . . . ?
C4 C3 C8 C9 178.1(4) . . . . ?
C2 C3 C8 C9 -1.8(5) . . . . ?
C7 C8 C9 C10 2.2(6) . . . . ?
C3 C8 C9 C10 -177.0(3) . . . . ?
C7 C8 C9 C14 -176.5(3) . . . . ?
C3 C8 C9 C14 4.3(5) . . . . ?
C14 C9 C10 C11 -0.4(6) . . . . ?
C8 C9 C10 C11 -179.1(4) . . . . ?
C9 C10 C11 C12 1.4(6) . . . . ?
C10 C11 C12 C13 -0.2(6) . . . . ?
C11 C12 C13 C14 -2.0(6) . . . . ?
C12 C13 C14 C9 3.0(6) . . . . ?
C12 C13 C14 C1 -177.1(4) . . . . ?
C10 C9 C14 C13 -1.8(5) . . . . ?
C8 C9 C14 C13 177.0(4) . . . . ?
C10 C9 C14 C1 178.3(3) . . . . ?
C8 C9 C14 C1 -2.9(5) . . . . ?
C2 C1 C14 C13 179.1(4) . . . . ?
N1 C1 C14 C13 -6.0(5) . . . . ?
C2 C1 C14 C9 -1.1(5) . . . . ?
N1 C1 C14 C9 173.8(3) . . . . ?
C1 N1 C15 C20 139.5(4) . . . . ?
C21 N1 C15 C20 -68.6(5) . . . . ?
C1 N1 C15 C16 -33.9(5) . . . . ?
C21 N1 C15 C16 118.0(4) . . . . ?
C20 C15 C16 C17 0.9(6) . . . . ?
N1 C15 C16 C17 174.6(4) . . . . ?
C20 C15 C16 N2 -178.4(3) . . . . ?
N1 C15 C16 N2 -4.7(5) . . . . ?
C27 N2 C16 C17 88.8(5) . . . . ?
C2 N2 C16 C17 -137.5(4) . . . . ?
C27 N2 C16 C15 -91.9(4) . . . . ?
C2 N2 C16 C15 41.8(5) . . . . ?
C15 C16 C17 C18 0.9(6) . . . . ?
N2 C16 C17 C18 -179.8(4) . . . . ?
C16 C17 C18 C19 -1.3(6) . . . . ?
C17 C18 C19 C20 -0.1(7) . . . . ?
C18 C19 C20 C15 1.9(7) . . . . ?
C16 C15 C20 C19 -2.3(6) . . . . ?
N1 C15 C20 C19 -175.7(4) . . . . ?
C15 N1 C21 C26 -124.9(4) . . . . ?
C1 N1 C21 C26 25.8(6) . . . . ?
C15 N1 C21 C22 58.4(6) . . . . ?
C1 N1 C21 C22 -151.0(4) . . . . ?
C26 C21 C22 C23 3.0(7) . . . . ?
N1 C21 C22 C23 179.8(4) . . . . ?
C21 C22 C23 C24 -2.0(8) . . . . ?
C22 C23 C24 C25 0.2(8) . . . . ?
C23 C24 C25 C26 0.6(8) . . . . ?
C22 C21 C26 C25 -2.2(7) . . . . ?
N1 C21 C26 C25 -179.0(4) . . . . ?
C24 C25 C26 C21 0.4(7) . . . . ?
C16 N2 C27 C28 150.3(4) . . . . ?
C2 N2 C27 C28 19.6(5) . . . . ?
C16 N2 C27 C32 -29.1(6) . . . . ?
C2 N2 C27 C32 -159.7(4) . . . . ?
C32 C27 C28 C29 2.1(7) . . . . ?
N2 C27 C28 C29 -177.3(4) . . . . ?
C27 C28 C29 C30 0.2(7) . . . . ?
C28 C29 C30 C31 -2.2(7) . . . . ?
C28 C29 C30 N3 173.1(4) . . . . ?
C44 N3 C30 C31 100.5(5) . . . . ?
C33 N3 C30 C31 -82.3(5) . . . . ?
C44 N3 C30 C29 -74.7(5) . . . . ?
C33 N3 C30 C29 102.4(5) . . . . ?
C29 C30 C31 C32 1.7(7) . . . . ?
N3 C30 C31 C32 -173.6(4) . . . . ?
C30 C31 C32 C27 0.8(7) . . . . ?
C28 C27 C32 C31 -2.6(7) . . . . ?
N2 C27 C32 C31 176.8(4) . . . . ?
C44 N3 C33 C34 178.2(4) . . . . ?
C30 N3 C33 C34 0.7(7) . . . . ?
C44 N3 C33 C38 -1.4(4) . . . . ?
C30 N3 C33 C38 -178.9(4) . . . . ?
N3 C33 C34 C35 -178.0(4) . . . . ?
C38 C33 C34 C35 1.5(6) . . . . ?
C33 C34 C35 C36 -0.2(7) . . . . ?
C34 C35 C36 C37 -0.8(8) . . . . ?
C35 C36 C37 C38 0.6(8) . . . . ?
C36 C37 C38 C33 0.7(7) . . . . ?
C36 C37 C38 C39 177.8(5) . . . . ?
C34 C33 C38 C37 -1.8(6) . . . . ?
N3 C33 C38 C37 177.8(4) . . . . ?
C34 C33 C38 C39 -179.6(4) . . . . ?
N3 C33 C38 C39 0.0(4) . . . . ?
C37 C38 C39 C40 0.2(9) . . . . ?
C33 C38 C39 C40 177.5(4) . . . . ?
C37 C38 C39 C44 -176.0(5) . . . . ?
C33 C38 C39 C44 1.4(4) . . . . ?
C44 C39 C40 C41 1.8(6) . . . . ?
C38 C39 C40 C41 -174.0(5) . . . . ?
C39 C40 C41 C42 -0.1(7) . . . . ?
C40 C41 C42 C43 -1.8(7) . . . . ?
C41 C42 C43 C44 1.7(6) . . . . ?
C42 C43 C44 N3 176.7(4) . . . . ?
C42 C43 C44 C39 0.1(6) . . . . ?
C33 N3 C44 C43 -174.7(4) . . . . ?
C30 N3 C44 C43 2.9(6) . . . . ?
C33 N3 C44 C39 2.3(4) . . . . ?
C30 N3 C44 C39 179.9(4) . . . . ?
C40 C39 C44 C43 -1.9(6) . . . . ?
C38 C39 C44 C43 175.0(4) . . . . ?
C40 C39 C44 N3 -179.1(3) . . . . ?
C38 C39 C44 N3 -2.2(4) . . . . ?
C1S Cl1 C1S Cl1 0.002(1) 2_666 . . 2_666 ?

_refine_diff_density_max         0.390
_refine_diff_density_min         -0.815
_refine_diff_density_rms         0.065

_shelxl_version_number           2013-4

_database_code_depnum_ccdc_archive 'CCDC 992519'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_dm14115

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C52 H36 Cl2 N4'
_chemical_formula_weight         787.75

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'
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                   9.4937(15)
_cell_length_b                   10.0154(16)
_cell_length_c                   21.812(4)
_cell_angle_alpha                101.429(4)
_cell_angle_beta                 97.164(5)
_cell_angle_gamma                104.122(3)
_cell_volume                     1938.5(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    140(2)
_cell_measurement_reflns_used    3246
_cell_measurement_theta_min      2.25
_cell_measurement_theta_max      30.25

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.350
_exptl_crystal_F_000             820
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_min          0.160
_exptl_absorpt_coefficient_mu    0.212
_shelx_estimated_absorpt_T_min   0.935
_shelx_estimated_absorpt_T_max   0.967
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4372
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      140(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19691
_diffrn_reflns_av_unetI/netI     0.1364
_diffrn_reflns_av_R_equivalents  0.0651
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         0.969
_diffrn_reflns_theta_max         30.698
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             11817
_reflns_number_gt                6209
_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    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_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)+(0.0947P)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         11817
_refine_ls_number_parameters     523
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1312
_refine_ls_R_factor_gt           0.0755
_refine_ls_wR_factor_ref         0.2283
_refine_ls_wR_factor_gt          0.1931
_refine_ls_goodness_of_fit_ref   0.962
_refine_ls_restrained_S_all      0.962
_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 0.4468(2) -0.2412(2) 0.12632(9) 0.0184(4) Uani 1 1 d . . . . .
N2 N 0.4159(2) 0.0285(2) 0.15220(9) 0.0178(4) Uani 1 1 d . . . . .
N3 N 0.8268(3) 0.4957(2) 0.64934(9) 0.0270(5) Uani 1 1 d . . . . .
N4 N 0.8766(2) 0.7062(2) 0.62356(10) 0.0252(5) Uani 1 1 d . . . . .
C1 C 0.5324(3) -0.1367(2) 0.09980(10) 0.0168(4) Uani 1 1 d . . . . .
C2 C 0.6238(2) -0.1783(2) 0.05581(10) 0.0170(5) Uani 1 1 d . . . . .
C3 C 0.6259(3) -0.3198(3) 0.03701(11) 0.0193(5) Uani 1 1 d . . . . .
H3 H 0.5681 -0.3893 0.0545 0.023 Uiso 1 1 calc R U . . .
C4 C 0.7103(3) -0.3599(3) -0.00646(12) 0.0244(5) Uani 1 1 d . . . . .
H4 H 0.7095 -0.4564 -0.0194 0.029 Uiso 1 1 calc R U . . .
C5 C 0.7967(3) -0.2575(3) -0.03126(11) 0.0248(5) Uani 1 1 d . . . . .
H5 H 0.8560 -0.2841 -0.0609 0.030 Uiso 1 1 calc R U . . .
C6 C 0.7967(3) -0.1176(3) -0.01307(11) 0.0234(5) Uani 1 1 d . . . . .
H6 H 0.8572 -0.0490 -0.0301 0.028 Uiso 1 1 calc R U . . .
C7 C 0.7092(3) -0.0743(2) 0.03020(10) 0.0175(5) Uani 1 1 d . . . . .
C8 C 0.7008(2) 0.0710(2) 0.04684(10) 0.0167(5) Uani 1 1 d . . . . .
C9 C 0.7858(3) 0.1801(3) 0.02364(11) 0.0221(5) Uani 1 1 d . . . . .
H9 H 0.8523 0.1594 -0.0036 0.027 Uiso 1 1 calc R U . . .
C10 C 0.7734(3) 0.3161(3) 0.03993(11) 0.0244(5) Uani 1 1 d . . . . .
H10 H 0.8326 0.3884 0.0244 0.029 Uiso 1 1 calc R U . . .
C11 C 0.6759(3) 0.3489(3) 0.07865(12) 0.0244(5) Uani 1 1 d . . . . .
H11 H 0.6688 0.4433 0.0896 0.029 Uiso 1 1 calc R U . . .
C12 C 0.5899(3) 0.2455(3) 0.10112(11) 0.0209(5) Uani 1 1 d . . . . .
H12 H 0.5212 0.2683 0.1267 0.025 Uiso 1 1 calc R U . . .
C13 C 0.6019(2) 0.1056(2) 0.08679(10) 0.0168(4) Uani 1 1 d . . . . .
C14 C 0.5192(2) -0.0021(2) 0.11326(10) 0.0168(4) Uani 1 1 d . . . . .
C15 C 0.2869(3) -0.0881(3) 0.14218(10) 0.0182(5) Uani 1 1 d . . . . .
C16 C 0.1470(3) -0.0684(3) 0.14076(11) 0.0231(5) Uani 1 1 d . . . . .
H16 H 0.1348 0.0242 0.1454 0.028 Uiso 1 1 calc R U . . .
C17 C 0.0252(3) -0.1836(3) 0.13254(12) 0.0278(6) Uani 1 1 d . . . . .
H17 H -0.0704 -0.1698 0.1324 0.033 Uiso 1 1 calc R U . . .
C18 C 0.0424(3) -0.3188(3) 0.12448(13) 0.0318(6) Uani 1 1 d . . . . .
H18 H -0.0410 -0.3972 0.1203 0.038 Uiso 1 1 calc R U . . .
C19 C 0.1809(3) -0.3406(3) 0.12247(12) 0.0253(5) Uani 1 1 d . . . . .
H19 H 0.1913 -0.4341 0.1147 0.030 Uiso 1 1 calc R U . . .
C20 C 0.3042(3) -0.2253(3) 0.13192(10) 0.0190(5) Uani 1 1 d . . . . .
C21 C 0.5244(3) -0.2924(3) 0.17354(11) 0.0229(5) Uani 1 1 d . . . . .
C22 C 0.6591(4) -0.2096(4) 0.2085(2) 0.0705(15) Uani 1 1 d . . . . .
H22 H 0.7005 -0.1185 0.2017 0.085 Uiso 1 1 calc R U . . .
C23 C 0.7349(5) -0.2598(5) 0.2543(2) 0.099(2) Uani 1 1 d . . . . .
H23 H 0.8270 -0.2015 0.2788 0.119 Uiso 1 1 calc R U . . .
C24 C 0.6789(5) -0.3901(4) 0.26396(18) 0.0631(12) Uani 1 1 d . . . . .
H24 H 0.7322 -0.4245 0.2942 0.076 Uiso 1 1 calc R U . . .
C25 C 0.5452(4) -0.4712(3) 0.22976(14) 0.0414(8) Uani 1 1 d . . . . .
H25 H 0.5035 -0.5615 0.2373 0.050 Uiso 1 1 calc R U . . .
C26 C 0.4688(4) -0.4235(3) 0.18400(13) 0.0346(7) Uani 1 1 d . . . . .
H26 H 0.3768 -0.4827 0.1597 0.042 Uiso 1 1 calc R U . . .
C27 C 0.4698(3) 0.1161(2) 0.21464(10) 0.0169(4) Uani 1 1 d . . . . .
C28 C 0.3753(3) 0.1557(3) 0.25426(11) 0.0217(5) Uani 1 1 d . . . . .
H28 H 0.2718 0.1269 0.2389 0.026 Uiso 1 1 calc R U . . .
C29 C 0.4305(3) 0.2366(3) 0.31596(11) 0.0229(5) Uani 1 1 d . . . . .
H29 H 0.3634 0.2605 0.3422 0.027 Uiso 1 1 calc R U . . .
C30 C 0.5803(3) 0.2835(3) 0.34043(10) 0.0202(5) Uani 1 1 d . . . . .
C31 C 0.6745(3) 0.2500(3) 0.29984(11) 0.0256(5) Uani 1 1 d . . . . .
H31 H 0.7782 0.2843 0.3145 0.031 Uiso 1 1 calc R U . . .
C32 C 0.6210(3) 0.1674(3) 0.23824(11) 0.0250(5) Uani 1 1 d . . . . .
H32 H 0.6886 0.1455 0.2118 0.030 Uiso 1 1 calc R U . . .
C33 C 0.6377(3) 0.3618(3) 0.40741(11) 0.0218(5) Uani 1 1 d . . . . .
C34 C 0.5642(3) 0.3239(3) 0.45580(11) 0.0266(6) Uani 1 1 d . . . . .
H34 H 0.4732 0.2516 0.4452 0.032 Uiso 1 1 calc R U . . .
C35 C 0.6228(3) 0.3906(3) 0.51918(12) 0.0283(6) Uani 1 1 d . . . . .
H35 H 0.5728 0.3621 0.5515 0.034 Uiso 1 1 calc R U . . .
C36 C 0.7539(3) 0.4986(3) 0.53571(11) 0.0232(5) Uani 1 1 d . . . . .
C37 C 0.8249(3) 0.5409(3) 0.48778(12) 0.0284(6) Uani 1 1 d . . . . .
H37 H 0.9128 0.6171 0.4983 0.034 Uiso 1 1 calc R U . . .
C38 C 0.7673(3) 0.4716(3) 0.42448(12) 0.0294(6) Uani 1 1 d . . . . .
H38 H 0.8177 0.5001 0.3922 0.035 Uiso 1 1 calc R U . . .
C39 C 0.8200(3) 0.5697(3) 0.60216(11) 0.0227(5) Uani 1 1 d . . . . .
C40 C 0.8955(3) 0.5968(3) 0.70518(11) 0.0276(6) Uani 1 1 d . . . . .
C41 C 0.9386(3) 0.5832(3) 0.76674(12) 0.0362(7) Uani 1 1 d . . . . .
H41 H 0.9203 0.4934 0.7771 0.043 Uiso 1 1 calc R U . . .
C42 C 1.0091(3) 0.7071(4) 0.81161(12) 0.0358(7) Uani 1 1 d . . . . .
H42 H 1.0381 0.7033 0.8544 0.043 Uiso 1 1 calc R U . . .
C43 C 1.0387(3) 0.8376(3) 0.79586(12) 0.0340(7) Uani 1 1 d . . . . .
H43 H 1.0884 0.9205 0.8282 0.041 Uiso 1 1 calc R U . . .
C44 C 0.9980(3) 0.8511(3) 0.73429(13) 0.0301(6) Uani 1 1 d . . . . .
H44 H 1.0188 0.9409 0.7240 0.036 Uiso 1 1 calc R U . . .
C45 C 0.9256(3) 0.7271(3) 0.68851(11) 0.0252(5) Uani 1 1 d . . . . .
C46 C 0.8029(3) 0.3463(3) 0.64270(12) 0.0302(6) Uani 1 1 d . . . . .
C47 C 0.8800(3) 0.2749(3) 0.60418(13) 0.0361(7) Uani 1 1 d . . . . .
H47 H 0.9430 0.3238 0.5804 0.043 Uiso 1 1 calc R U . . .
C48 C 0.8652(4) 0.1325(4) 0.60037(16) 0.0443(8) Uani 1 1 d . . . . .
H48 H 0.9186 0.0835 0.5744 0.053 Uiso 1 1 calc R U . . .
C49 C 0.7716(4) 0.0620(4) 0.63488(17) 0.0486(9) Uani 1 1 d . . . . .
H49 H 0.7607 -0.0359 0.6324 0.058 Uiso 1 1 calc R U . . .
C50 C 0.6937(4) 0.1339(4) 0.67301(17) 0.0507(9) Uani 1 1 d . . . . .
H50 H 0.6301 0.0851 0.6966 0.061 Uiso 1 1 calc R U . . .
C51 C 0.7084(4) 0.2749(4) 0.67661(14) 0.0407(7) Uani 1 1 d . . . . .
H51 H 0.6540 0.3236 0.7022 0.049 Uiso 1 1 calc R U . . .
C52 C 0.6962(5) 0.9981(5) 0.4316(3) 0.0858(17) Uani 1 1 d . . . . .
H52A H 0.6196 0.9775 0.3932 0.103 Uiso 1 1 calc R U . . .
H52B H 0.6631 1.0513 0.4678 0.103 Uiso 1 1 calc R U . . .
Cl1 Cl 0.86305(10) 1.10275(10) 0.41946(5) 0.0545(3) Uani 1 1 d . . . . .
Cl2 Cl 0.71656(14) 0.83747(13) 0.44775(6) 0.0830(4) 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 C20 1.418(3) . ?
N1 C1 1.426(3) . ?
N1 C21 1.439(3) . ?
N2 C27 1.421(3) . ?
N2 C14 1.424(3) . ?
N2 C15 1.430(3) . ?
N3 C39 1.386(3) . ?
N3 C40 1.387(3) . ?
N3 C46 1.432(4) . ?
N4 C39 1.305(3) . ?
N4 C45 1.392(3) . ?
C1 C14 1.362(3) . ?
C1 C2 1.439(3) . ?
C2 C3 1.401(3) . ?
C2 C7 1.409(3) . ?
C3 C4 1.378(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.392(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.378(4) . ?
C5 H5 0.9500 . ?
C6 C7 1.407(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.453(3) . ?
C8 C9 1.412(3) . ?
C8 C13 1.415(3) . ?
C9 C10 1.375(4) . ?
C9 H9 0.9500 . ?
C10 C11 1.382(4) . ?
C10 H10 0.9500 . ?
C11 C12 1.366(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.410(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.435(3) . ?
C15 C16 1.387(3) . ?
C15 C20 1.400(3) . ?
C16 C17 1.385(4) . ?
C16 H16 0.9500 . ?
C17 C18 1.382(4) . ?
C17 H17 0.9500 . ?
C18 C19 1.389(4) . ?
C18 H18 0.9500 . ?
C19 C20 1.391(3) . ?
C19 H19 0.9500 . ?
C21 C26 1.366(4) . ?
C21 C22 1.376(4) . ?
C22 C23 1.401(4) . ?
C22 H22 0.9500 . ?
C23 C24 1.353(5) . ?
C23 H23 0.9500 . ?
C24 C25 1.359(5) . ?
C24 H24 0.9500 . ?
C25 C26 1.388(4) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
C27 C28 1.392(3) . ?
C27 C32 1.394(3) . ?
C28 C29 1.388(3) . ?
C28 H28 0.9500 . ?
C29 C30 1.383(3) . ?
C29 H29 0.9500 . ?
C30 C31 1.386(4) . ?
C30 C33 1.479(3) . ?
C31 C32 1.390(3) . ?
C31 H31 0.9500 . ?
C32 H32 0.9500 . ?
C33 C38 1.387(4) . ?
C33 C34 1.399(3) . ?
C34 C35 1.388(3) . ?
C34 H34 0.9500 . ?
C35 C36 1.387(4) . ?
C35 H35 0.9500 . ?
C36 C37 1.392(4) . ?
C36 C39 1.466(3) . ?
C37 C38 1.391(3) . ?
C37 H37 0.9500 . ?
C38 H38 0.9500 . ?
C40 C45 1.396(4) . ?
C40 C41 1.397(3) . ?
C41 C42 1.377(4) . ?
C41 H41 0.9500 . ?
C42 C43 1.389(5) . ?
C42 H42 0.9500 . ?
C43 C44 1.392(4) . ?
C43 H43 0.9500 . ?
C44 C45 1.390(4) . ?
C44 H44 0.9500 . ?
C46 C47 1.387(4) . ?
C46 C51 1.388(4) . ?
C47 C48 1.383(4) . ?
C47 H47 0.9500 . ?
C48 C49 1.388(5) . ?
C48 H48 0.9500 . ?
C49 C50 1.390(5) . ?
C49 H49 0.9500 . ?
C50 C51 1.370(5) . ?
C50 H50 0.9500 . ?
C51 H51 0.9500 . ?
C52 Cl1 1.755(4) . ?
C52 Cl2 1.763(5) . ?
C52 H52A 0.9900 . ?
C52 H52B 0.9900 . ?

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
C20 N1 C1 113.53(18) . . ?
C20 N1 C21 119.65(19) . . ?
C1 N1 C21 117.35(19) . . ?
C27 N2 C14 118.91(18) . . ?
C27 N2 C15 118.36(18) . . ?
C14 N2 C15 112.59(19) . . ?
C39 N3 C40 105.9(2) . . ?
C39 N3 C46 128.7(2) . . ?
C40 N3 C46 123.9(2) . . ?
C39 N4 C45 105.7(2) . . ?
C14 C1 N1 119.6(2) . . ?
C14 C1 C2 121.2(2) . . ?
N1 C1 C2 119.1(2) . . ?
C3 C2 C7 119.9(2) . . ?
C3 C2 C1 121.2(2) . . ?
C7 C2 C1 118.8(2) . . ?
C4 C3 C2 121.1(2) . . ?
C4 C3 H3 119.5 . . ?
C2 C3 H3 119.5 . . ?
C3 C4 C5 119.3(2) . . ?
C3 C4 H4 120.3 . . ?
C5 C4 H4 120.3 . . ?
C6 C5 C4 120.4(2) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
C5 C6 C7 121.4(2) . . ?
C5 C6 H6 119.3 . . ?
C7 C6 H6 119.3 . . ?
C6 C7 C2 117.8(2) . . ?
C6 C7 C8 122.1(2) . . ?
C2 C7 C8 120.0(2) . . ?
C9 C8 C13 118.0(2) . . ?
C9 C8 C7 122.5(2) . . ?
C13 C8 C7 119.4(2) . . ?
C10 C9 C8 120.8(2) . . ?
C10 C9 H9 119.6 . . ?
C8 C9 H9 119.6 . . ?
C9 C10 C11 120.9(2) . . ?
C9 C10 H10 119.6 . . ?
C11 C10 H10 119.6 . . ?
C12 C11 C10 120.0(2) . . ?
C12 C11 H11 120.0 . . ?
C10 C11 H11 120.0 . . ?
C11 C12 C13 120.8(2) . . ?
C11 C12 H12 119.6 . . ?
C13 C12 H12 119.6 . . ?
C12 C13 C8 119.4(2) . . ?
C12 C13 C14 121.5(2) . . ?
C8 C13 C14 119.0(2) . . ?
C1 C14 N2 118.4(2) . . ?
C1 C14 C13 121.2(2) . . ?
N2 C14 C13 120.3(2) . . ?
C16 C15 C20 120.0(2) . . ?
C16 C15 N2 121.7(2) . . ?
C20 C15 N2 118.2(2) . . ?
C17 C16 C15 120.0(3) . . ?
C17 C16 H16 120.0 . . ?
C15 C16 H16 120.0 . . ?
C18 C17 C16 120.1(3) . . ?
C18 C17 H17 120.0 . . ?
C16 C17 H17 120.0 . . ?
C17 C18 C19 120.4(2) . . ?
C17 C18 H18 119.8 . . ?
C19 C18 H18 119.8 . . ?
C18 C19 C20 119.8(3) . . ?
C18 C19 H19 120.1 . . ?
C20 C19 H19 120.1 . . ?
C19 C20 C15 119.5(2) . . ?
C19 C20 N1 122.4(2) . . ?
C15 C20 N1 117.9(2) . . ?
C26 C21 C22 118.6(2) . . ?
C26 C21 N1 121.5(2) . . ?
C22 C21 N1 119.9(2) . . ?
C21 C22 C23 119.9(3) . . ?
C21 C22 H22 120.1 . . ?
C23 C22 H22 120.1 . . ?
C24 C23 C22 121.0(3) . . ?
C24 C23 H23 119.5 . . ?
C22 C23 H23 119.5 . . ?
C23 C24 C25 119.0(3) . . ?
C23 C24 H24 120.5 . . ?
C25 C24 H24 120.5 . . ?
C24 C25 C26 120.8(3) . . ?
C24 C25 H25 119.6 . . ?
C26 C25 H25 119.6 . . ?
C21 C26 C25 120.7(3) . . ?
C21 C26 H26 119.6 . . ?
C25 C26 H26 119.6 . . ?
C28 C27 C32 117.4(2) . . ?
C28 C27 N2 122.0(2) . . ?
C32 C27 N2 120.6(2) . . ?
C29 C28 C27 120.8(2) . . ?
C29 C28 H28 119.6 . . ?
C27 C28 H28 119.6 . . ?
C30 C29 C28 122.0(2) . . ?
C30 C29 H29 119.0 . . ?
C28 C29 H29 119.0 . . ?
C29 C30 C31 117.0(2) . . ?
C29 C30 C33 121.7(2) . . ?
C31 C30 C33 121.3(2) . . ?
C30 C31 C32 121.7(2) . . ?
C30 C31 H31 119.2 . . ?
C32 C31 H31 119.2 . . ?
C31 C32 C27 121.0(2) . . ?
C31 C32 H32 119.5 . . ?
C27 C32 H32 119.5 . . ?
C38 C33 C34 118.1(2) . . ?
C38 C33 C30 121.4(2) . . ?
C34 C33 C30 120.5(2) . . ?
C35 C34 C33 120.7(2) . . ?
C35 C34 H34 119.6 . . ?
C33 C34 H34 119.6 . . ?
C36 C35 C34 120.6(2) . . ?
C36 C35 H35 119.7 . . ?
C34 C35 H35 119.7 . . ?
C35 C36 C37 119.1(2) . . ?
C35 C36 C39 122.0(2) . . ?
C37 C36 C39 118.9(2) . . ?
C38 C37 C36 120.0(2) . . ?
C38 C37 H37 120.0 . . ?
C36 C37 H37 120.0 . . ?
C33 C38 C37 121.4(2) . . ?
C33 C38 H38 119.3 . . ?
C37 C38 H38 119.3 . . ?
N4 C39 N3 112.9(2) . . ?
N4 C39 C36 124.8(2) . . ?
N3 C39 C36 122.2(2) . . ?
N3 C40 C45 105.9(2) . . ?
N3 C40 C41 131.2(3) . . ?
C45 C40 C41 122.8(3) . . ?
C42 C41 C40 116.3(3) . . ?
C42 C41 H41 121.9 . . ?
C40 C41 H41 121.9 . . ?
C41 C42 C43 121.6(2) . . ?
C41 C42 H42 119.2 . . ?
C43 C42 H42 119.2 . . ?
C42 C43 C44 122.2(3) . . ?
C42 C43 H43 118.9 . . ?
C44 C43 H43 118.9 . . ?
C45 C44 C43 117.0(3) . . ?
C45 C44 H44 121.5 . . ?
C43 C44 H44 121.5 . . ?
C44 C45 N4 130.2(3) . . ?
C44 C45 C40 120.2(2) . . ?
N4 C45 C40 109.6(2) . . ?
C47 C46 C51 120.3(3) . . ?
C47 C46 N3 119.4(3) . . ?
C51 C46 N3 120.3(3) . . ?
C48 C47 C46 120.1(3) . . ?
C48 C47 H47 120.0 . . ?
C46 C47 H47 120.0 . . ?
C47 C48 C49 119.4(3) . . ?
C47 C48 H48 120.3 . . ?
C49 C48 H48 120.3 . . ?
C48 C49 C50 120.3(3) . . ?
C48 C49 H49 119.9 . . ?
C50 C49 H49 119.9 . . ?
C51 C50 C49 120.2(3) . . ?
C51 C50 H50 119.9 . . ?
C49 C50 H50 119.9 . . ?
C50 C51 C46 119.7(3) . . ?
C50 C51 H51 120.1 . . ?
C46 C51 H51 120.1 . . ?
Cl1 C52 Cl2 111.3(3) . . ?
Cl1 C52 H52A 109.4 . . ?
Cl2 C52 H52A 109.4 . . ?
Cl1 C52 H52B 109.4 . . ?
Cl2 C52 H52B 109.4 . . ?
H52A C52 H52B 108.0 . . ?

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
C20 N1 C1 C14 35.0(3) . . . . ?
C21 N1 C1 C14 -111.4(2) . . . . ?
C20 N1 C1 C2 -140.8(2) . . . . ?
C21 N1 C1 C2 72.8(3) . . . . ?
C14 C1 C2 C3 -173.4(2) . . . . ?
N1 C1 C2 C3 2.3(3) . . . . ?
C14 C1 C2 C7 4.8(3) . . . . ?
N1 C1 C2 C7 -179.44(19) . . . . ?
C7 C2 C3 C4 -0.1(3) . . . . ?
C1 C2 C3 C4 178.2(2) . . . . ?
C2 C3 C4 C5 1.1(4) . . . . ?
C3 C4 C5 C6 -0.7(4) . . . . ?
C4 C5 C6 C7 -0.7(4) . . . . ?
C5 C6 C7 C2 1.6(3) . . . . ?
C5 C6 C7 C8 -176.0(2) . . . . ?
C3 C2 C7 C6 -1.2(3) . . . . ?
C1 C2 C7 C6 -179.5(2) . . . . ?
C3 C2 C7 C8 176.49(19) . . . . ?
C1 C2 C7 C8 -1.8(3) . . . . ?
C6 C7 C8 C9 -3.6(3) . . . . ?
C2 C7 C8 C9 178.76(19) . . . . ?
C6 C7 C8 C13 175.1(2) . . . . ?
C2 C7 C8 C13 -2.5(3) . . . . ?
C13 C8 C9 C10 0.5(3) . . . . ?
C7 C8 C9 C10 179.3(2) . . . . ?
C8 C9 C10 C11 -1.0(3) . . . . ?
C9 C10 C11 C12 -0.2(4) . . . . ?
C10 C11 C12 C13 1.8(3) . . . . ?
C11 C12 C13 C8 -2.2(3) . . . . ?
C11 C12 C13 C14 176.0(2) . . . . ?
C9 C8 C13 C12 1.0(3) . . . . ?
C7 C8 C13 C12 -177.78(19) . . . . ?
C9 C8 C13 C14 -177.24(19) . . . . ?
C7 C8 C13 C14 4.0(3) . . . . ?
N1 C1 C14 N2 -1.9(3) . . . . ?
C2 C1 C14 N2 173.86(19) . . . . ?
N1 C1 C14 C13 -179.12(19) . . . . ?
C2 C1 C14 C13 -3.4(3) . . . . ?
C27 N2 C14 C1 110.4(2) . . . . ?
C15 N2 C14 C1 -34.4(3) . . . . ?
C27 N2 C14 C13 -72.3(3) . . . . ?
C15 N2 C14 C13 142.9(2) . . . . ?
C12 C13 C14 C1 -179.3(2) . . . . ?
C8 C13 C14 C1 -1.1(3) . . . . ?
C12 C13 C14 N2 3.5(3) . . . . ?
C8 C13 C14 N2 -178.28(19) . . . . ?
C27 N2 C15 C16 74.9(3) . . . . ?
C14 N2 C15 C16 -140.0(2) . . . . ?
C27 N2 C15 C20 -106.8(2) . . . . ?
C14 N2 C15 C20 38.2(3) . . . . ?
C20 C15 C16 C17 3.4(3) . . . . ?
N2 C15 C16 C17 -178.4(2) . . . . ?
C15 C16 C17 C18 -1.3(4) . . . . ?
C16 C17 C18 C19 -2.1(4) . . . . ?
C17 C18 C19 C20 3.4(4) . . . . ?
C18 C19 C20 C15 -1.2(3) . . . . ?
C18 C19 C20 N1 -175.8(2) . . . . ?
C16 C15 C20 C19 -2.2(3) . . . . ?
N2 C15 C20 C19 179.6(2) . . . . ?
C16 C15 C20 N1 172.7(2) . . . . ?
N2 C15 C20 N1 -5.6(3) . . . . ?
C1 N1 C20 C19 144.1(2) . . . . ?
C21 N1 C20 C19 -70.4(3) . . . . ?
C1 N1 C20 C15 -30.6(3) . . . . ?
C21 N1 C20 C15 115.0(2) . . . . ?
C20 N1 C21 C26 61.2(3) . . . . ?
C1 N1 C21 C26 -154.6(3) . . . . ?
C20 N1 C21 C22 -119.9(4) . . . . ?
C1 N1 C21 C22 24.3(4) . . . . ?
C26 C21 C22 C23 -0.8(7) . . . . ?
N1 C21 C22 C23 -179.7(5) . . . . ?
C21 C22 C23 C24 1.1(9) . . . . ?
C22 C23 C24 C25 -1.7(9) . . . . ?
C23 C24 C25 C26 2.1(7) . . . . ?
C22 C21 C26 C25 1.1(5) . . . . ?
N1 C21 C26 C25 -180.0(3) . . . . ?
C24 C25 C26 C21 -1.8(5) . . . . ?
C14 N2 C27 C28 177.0(2) . . . . ?
C15 N2 C27 C28 -40.2(3) . . . . ?
C14 N2 C27 C32 -2.2(3) . . . . ?
C15 N2 C27 C32 140.6(2) . . . . ?
C32 C27 C28 C29 -3.4(4) . . . . ?
N2 C27 C28 C29 177.3(2) . . . . ?
C27 C28 C29 C30 1.2(4) . . . . ?
C28 C29 C30 C31 2.0(4) . . . . ?
C28 C29 C30 C33 -176.1(2) . . . . ?
C29 C30 C31 C32 -3.0(4) . . . . ?
C33 C30 C31 C32 175.2(2) . . . . ?
C30 C31 C32 C27 0.7(4) . . . . ?
C28 C27 C32 C31 2.5(4) . . . . ?
N2 C27 C32 C31 -178.2(2) . . . . ?
C29 C30 C33 C38 -143.3(3) . . . . ?
C31 C30 C33 C38 38.7(4) . . . . ?
C29 C30 C33 C34 38.6(4) . . . . ?
C31 C30 C33 C34 -139.4(3) . . . . ?
C38 C33 C34 C35 -2.6(4) . . . . ?
C30 C33 C34 C35 175.6(2) . . . . ?
C33 C34 C35 C36 1.5(4) . . . . ?
C34 C35 C36 C37 1.0(4) . . . . ?
C34 C35 C36 C39 -179.0(3) . . . . ?
C35 C36 C37 C38 -2.4(4) . . . . ?
C39 C36 C37 C38 177.7(3) . . . . ?
C34 C33 C38 C37 1.2(4) . . . . ?
C30 C33 C38 C37 -176.9(3) . . . . ?
C36 C37 C38 C33 1.2(4) . . . . ?
C45 N4 C39 N3 0.4(3) . . . . ?
C45 N4 C39 C36 179.8(2) . . . . ?
C40 N3 C39 N4 -0.5(3) . . . . ?
C46 N3 C39 N4 -166.8(3) . . . . ?
C40 N3 C39 C36 -179.9(2) . . . . ?
C46 N3 C39 C36 13.9(4) . . . . ?
C35 C36 C39 N4 -136.7(3) . . . . ?
C37 C36 C39 N4 43.3(4) . . . . ?
C35 C36 C39 N3 42.6(4) . . . . ?
C37 C36 C39 N3 -137.4(3) . . . . ?
C39 N3 C40 C45 0.4(3) . . . . ?
C46 N3 C40 C45 167.4(3) . . . . ?
C39 N3 C40 C41 -176.1(3) . . . . ?
C46 N3 C40 C41 -9.1(5) . . . . ?
N3 C40 C41 C42 178.2(3) . . . . ?
C45 C40 C41 C42 2.2(4) . . . . ?
C40 C41 C42 C43 -1.6(5) . . . . ?
C41 C42 C43 C44 0.6(5) . . . . ?
C42 C43 C44 C45 0.0(4) . . . . ?
C43 C44 C45 N4 -177.5(3) . . . . ?
C43 C44 C45 C40 0.6(4) . . . . ?
C39 N4 C45 C44 178.1(3) . . . . ?
C39 N4 C45 C40 -0.2(3) . . . . ?
N3 C40 C45 C44 -178.6(2) . . . . ?
C41 C40 C45 C44 -1.7(4) . . . . ?
N3 C40 C45 N4 -0.2(3) . . . . ?
C41 C40 C45 N4 176.7(3) . . . . ?
C39 N3 C46 C47 52.4(4) . . . . ?
C40 N3 C46 C47 -111.6(3) . . . . ?
C39 N3 C46 C51 -130.4(3) . . . . ?
C40 N3 C46 C51 65.7(4) . . . . ?
C51 C46 C47 C48 -1.3(4) . . . . ?
N3 C46 C47 C48 176.0(3) . . . . ?
C46 C47 C48 C49 0.7(5) . . . . ?
C47 C48 C49 C50 -0.1(5) . . . . ?
C48 C49 C50 C51 0.2(5) . . . . ?
C49 C50 C51 C46 -0.9(5) . . . . ?
C47 C46 C51 C50 1.4(4) . . . . ?
N3 C46 C51 C50 -175.8(3) . . . . ?

_refine_diff_density_max         0.516
_refine_diff_density_min         -0.784
_refine_diff_density_rms         0.082

_shelxl_version_number           2013-4

_database_code_depnum_ccdc_archive 'CCDC 992520'
