# Electronic Supplementary Material (ESI) for Chemical Science.
# 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 
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# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
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data_mo_171030a_0m
_database_code_depnum_ccdc_archive 'CCDC 1589253'
_audit_update_record             
;
2017-12-05 deposited with the CCDC.
2018-02-02 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            'C44 H36 N2'
_chemical_formula_weight         592.75

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

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

_cell_length_a                   8.6947(17)
_cell_length_b                   17.563(4)
_cell_length_c                   10.737(2)
_cell_angle_alpha                90
_cell_angle_beta                 97.361(4)
_cell_angle_gamma                90
_cell_volume                     1626.1(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    1334
_cell_measurement_theta_min      2.24
_cell_measurement_theta_max      21.23

_exptl_crystal_description       needle
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.211
_exptl_crystal_F_000             628
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.060
_exptl_crystal_size_mid          0.030
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    0.070
_shelx_estimated_absorpt_T_min   0.996
_shelx_estimated_absorpt_T_max   0.999
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(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            11461
_diffrn_reflns_av_unetI/netI     0.0870
_diffrn_reflns_av_R_equivalents  0.1081
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.237
_diffrn_reflns_theta_max         24.996
_diffrn_reflns_theta_full        24.996
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measured_fraction_theta_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_point_group_measured_fraction_full 0.987
_reflns_number_total             2832
_reflns_number_gt                1499
_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-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.2000P)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     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.009(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2832
_refine_ls_number_parameters     259
_refine_ls_number_restraints     69
_refine_ls_R_factor_all          0.1702
_refine_ls_R_factor_gt           0.1127
_refine_ls_wR_factor_ref         0.3594
_refine_ls_wR_factor_gt          0.3160
_refine_ls_goodness_of_fit_ref   1.115
_refine_ls_restrained_S_all      1.148
_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 0.2475(6) 0.4962(3) 0.9398(7) 0.082(2) Uani 1 1 d . . . . .
H1A H 0.2000 0.4778 0.8576 0.123 Uiso 1 1 calc R U . . .
H1B H 0.1662 0.5132 0.9887 0.123 Uiso 1 1 calc R U . . .
H1C H 0.3070 0.4550 0.9846 0.123 Uiso 1 1 calc R U . . .
C2 C 0.3543(5) 0.5620(3) 0.9220(5) 0.0562(14) Uani 1 1 d . . . . .
C3 C 0.4240(6) 0.5685(3) 0.8138(5) 0.0604(14) Uani 1 1 d . . . . .
H3 H 0.4060 0.5303 0.7510 0.072 Uiso 1 1 calc R U . . .
C4 C 0.5186(6) 0.6290(3) 0.7949(5) 0.0572(13) Uani 1 1 d . . . . .
H4 H 0.5641 0.6325 0.7192 0.069 Uiso 1 1 calc R U . . .
C5 C 0.5481(5) 0.6852(3) 0.8865(4) 0.0507(13) Uani 1 1 d . . . . .
C6 C 0.4828(5) 0.6780(3) 0.9957(4) 0.0521(13) Uani 1 1 d . . . . .
H6 H 0.5038 0.7150 1.0601 0.062 Uiso 1 1 calc R U . . .
C7 C 0.3871(5) 0.6177(3) 1.0122(5) 0.0548(13) Uani 1 1 d . . . . .
H7 H 0.3421 0.6141 1.0881 0.066 Uiso 1 1 calc R U . . .
C8 C 0.7757(6) 0.7406(3) 0.8052(5) 0.0555(14) Uani 1 1 d . . . . .
C9 C 0.8708(6) 0.6777(3) 0.8284(5) 0.0594(14) Uani 1 1 d . . . . .
H9 H 0.8477 0.6405 0.8874 0.071 Uiso 1 1 calc R U . . .
C10 C 0.9990(6) 0.6688(3) 0.7663(5) 0.0668(16) Uani 1 1 d . . . . .
H10 H 1.0625 0.6250 0.7818 0.080 Uiso 1 1 calc R U . . .
C11 C 1.0361(6) 0.7234(4) 0.6812(5) 0.0727(17) Uani 1 1 d . . . . .
C12 C 0.9449(7) 0.7866(3) 0.6648(6) 0.0742(17) Uani 1 1 d . . . . .
H12 H 0.9717 0.8257 0.6103 0.089 Uiso 1 1 calc R U . . .
C13 C 0.8155(6) 0.7955(3) 0.7245(5) 0.0605(14) Uani 1 1 d . . . . .
H13 H 0.7533 0.8399 0.7098 0.073 Uiso 1 1 calc R U . . .
C14 C 1.1730(8) 0.7094(4) 0.6057(7) 0.104(2) Uani 1 1 d . . . . .
H14A H 1.1722 0.7481 0.5400 0.155 Uiso 1 1 calc R U . . .
H14B H 1.1629 0.6587 0.5672 0.155 Uiso 1 1 calc R U . . .
H14C H 1.2708 0.7123 0.6621 0.155 Uiso 1 1 calc R U . . .
C15 C 0.6240(7) 0.8269(3) 0.9112(7) 0.060(4) Uani 0.5 1 d G . P A -1
C16 C 0.7644(6) 0.8556(4) 0.9688(7) 0.062(3) Uani 0.5 1 d G U P A -1
H16 H 0.8563 0.8262 0.9705 0.075 Uiso 0.5 1 calc R U P A -1
C17 C 0.7702(5) 0.9273(4) 1.0240(6) 0.054(2) Uani 0.5 1 d G U P A -1
H17 H 0.8661 0.9469 1.0633 0.065 Uiso 0.5 1 calc R U P A -1
C18 C 0.6357(6) 0.9703(3) 1.0215(7) 0.053(4) Uani 0.5 1 d G U P A -1
C19 C 0.4953(6) 0.9416(3) 0.9640(7) 0.037(3) Uani 0.5 1 d DG U P A -1
C20 C 0.4895(6) 0.8699(3) 0.9088(6) 0.049(2) Uani 0.5 1 d DG U P A -1
C21 C 0.3497(8) 0.8437(5) 0.8449(15) 0.103(6) Uani 0.5 1 d D U P A -1
H21 H 0.3444 0.7947 0.8074 0.124 Uiso 0.5 1 calc R U P A -1
C22 C 0.2180(8) 0.8895(6) 0.8361(16) 0.134(6) Uani 0.5 1 d D U P A -1
H22 H 0.1237 0.8717 0.7910 0.161 Uiso 0.5 1 calc R U P A -1
C23 C 0.2228(6) 0.9609(4) 0.8925(10) 0.079(3) Uani 0.5 1 d D U P A -1
H23 H 0.1313 0.9909 0.8870 0.095 Uiso 0.5 1 calc R U P A -1
C24 C 0.3602(7) 0.9888(4) 0.9569(9) 0.053(4) Uani 0.5 1 d D . P A -1
C25 C 0.3463(5) 1.1214(4) 1.0408(6) 0.044(2) Uani 0.5 1 d G . P A -1
H25 H 0.2382 1.1264 1.0142 0.053 Uiso 0.5 1 calc R U P A -1
C26 C 0.4286(8) 1.1817(3) 1.1009(7) 0.065(4) Uani 0.5 1 d G . P A -1
C27 C 0.5867(8) 1.1744(3) 1.1397(7) 0.053(3) Uani 0.5 1 d G . P A -1
H27 H 0.6430 1.2156 1.1809 0.064 Uiso 0.5 1 calc R U P A -1
C28 C 0.6624(5) 1.1069(3) 1.1184(6) 0.045(2) Uani 0.5 1 d G . P A -1
H28 H 0.7704 1.1019 1.1449 0.055 Uiso 0.5 1 calc R U P A -1
C29 C 0.5800(6) 1.0466(3) 1.0582(6) 0.038(3) Uani 0.5 1 d G U P A -1
C30 C 0.4220(6) 1.0539(3) 1.0194(6) 0.035(3) Uani 0.5 1 d G U P A -1
N1 N 0.6432(5) 0.7492(2) 0.8687(4) 0.0592(12) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.510(7) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C7 1.380(7) . ?
C2 C3 1.382(7) . ?
C3 C4 1.375(7) . ?
C3 H3 0.9500 . ?
C4 C5 1.395(6) . ?
C4 H4 0.9500 . ?
C5 C6 1.372(6) . ?
C5 N1 1.422(6) . ?
C6 C7 1.373(7) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 C13 1.370(6) . ?
C8 C9 1.382(6) . ?
C8 N1 1.420(6) . ?
C9 C10 1.379(6) . ?
C9 H9 0.9500 . ?
C10 C11 1.390(7) . ?
C10 H10 0.9500 . ?
C11 C12 1.363(8) . ?
C11 C14 1.543(8) . ?
C12 C13 1.374(7) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 C16 1.3900 . ?
C15 C20 1.3900 . ?
C15 N1 1.456(5) . ?
C16 C17 1.3900 . ?
C16 H16 0.9500 . ?
C17 C18 1.3900 . ?
C17 H17 0.9500 . ?
C18 C19 1.3900 . ?
C18 C29 1.494(6) . ?
C19 C20 1.3900 . ?
C19 C24 1.431(6) . ?
C20 C21 1.3948 . ?
C21 C22 1.3924(10) . ?
C21 H21 0.9500 . ?
C22 C23 1.3914(10) . ?
C22 H22 0.9500 . ?
C23 C24 1.3908(11) . ?
C23 H23 0.9500 . ?
C24 C30 1.397(9) . ?
C25 C26 1.3900 . ?
C25 C30 1.3900 . ?
C25 H25 0.9500 . ?
C26 C27 1.3900 . ?
C27 C28 1.3900 . ?
C27 H27 0.9500 . ?
C28 C29 1.3900 . ?
C28 H28 0.9500 . ?
C29 C30 1.3900 . ?

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
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C7 C2 C3 117.3(4) . . ?
C7 C2 C1 121.9(5) . . ?
C3 C2 C1 120.9(5) . . ?
C4 C3 C2 121.5(4) . . ?
C4 C3 H3 119.2 . . ?
C2 C3 H3 119.2 . . ?
C3 C4 C5 120.2(5) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
C6 C5 C4 118.6(4) . . ?
C6 C5 N1 119.9(4) . . ?
C4 C5 N1 121.5(4) . . ?
C5 C6 C7 120.4(4) . . ?
C5 C6 H6 119.8 . . ?
C7 C6 H6 119.8 . . ?
C6 C7 C2 122.0(5) . . ?
C6 C7 H7 119.0 . . ?
C2 C7 H7 119.0 . . ?
C13 C8 C9 118.9(5) . . ?
C13 C8 N1 121.0(4) . . ?
C9 C8 N1 120.1(4) . . ?
C10 C9 C8 120.3(4) . . ?
C10 C9 H9 119.8 . . ?
C8 C9 H9 119.8 . . ?
C9 C10 C11 120.6(5) . . ?
C9 C10 H10 119.7 . . ?
C11 C10 H10 119.7 . . ?
C12 C11 C10 117.8(5) . . ?
C12 C11 C14 122.4(5) . . ?
C10 C11 C14 119.7(5) . . ?
C11 C12 C13 122.0(5) . . ?
C11 C12 H12 119.0 . . ?
C13 C12 H12 119.0 . . ?
C8 C13 C12 120.2(5) . . ?
C8 C13 H13 119.9 . . ?
C12 C13 H13 119.9 . . ?
C11 C14 H14A 109.5 . . ?
C11 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C11 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C16 C15 C20 120.0 . . ?
C16 C15 N1 110.5(4) . . ?
C20 C15 N1 129.4(4) . . ?
C15 C16 C17 120.0 . . ?
C15 C16 H16 120.0 . . ?
C17 C16 H16 120.0 . . ?
C18 C17 C16 120.0 . . ?
C18 C17 H17 120.0 . . ?
C16 C17 H17 120.0 . . ?
C17 C18 C19 120.0 . . ?
C17 C18 C29 141.5(4) . . ?
C19 C18 C29 98.4(4) . . ?
C20 C19 C18 120.0 . . ?
C20 C19 C24 121.1(2) . . ?
C18 C19 C24 118.8(2) . . ?
C19 C20 C15 120.0 . . ?
C19 C20 C21 119.37(15) . . ?
C15 C20 C21 120.52(17) . . ?
C22 C21 C20 120.01(13) . . ?
C22 C21 H21 120.0 . . ?
C20 C21 H21 120.0 . . ?
C23 C22 C21 120.81(17) . . ?
C23 C22 H22 119.6 . . ?
C21 C22 H22 119.6 . . ?
C24 C23 C22 120.68(19) . . ?
C24 C23 H23 119.7 . . ?
C22 C23 H23 119.7 . . ?
C23 C24 C30 141.2(5) . . ?
C23 C24 C19 118.0(3) . . ?
C30 C24 C19 100.7(4) . . ?
C26 C25 C30 120.0 . . ?
C26 C25 H25 120.0 . . ?
C30 C25 H25 120.0 . . ?
C25 C26 C27 120.0 . . ?
C28 C27 C26 120.0 . . ?
C28 C27 H27 120.0 . . ?
C26 C27 H27 120.0 . . ?
C27 C28 C29 120.0 . . ?
C27 C28 H28 120.0 . . ?
C29 C28 H28 120.0 . . ?
C30 C29 C28 120.0 . . ?
C30 C29 C18 110.2(4) . . ?
C28 C29 C18 129.8(4) . . ?
C29 C30 C25 120.0 . . ?
C29 C30 C24 111.9(5) . . ?
C25 C30 C24 128.1(5) . . ?
C8 N1 C5 120.1(3) . . ?
C8 N1 C15 112.6(4) . . ?
C5 N1 C15 127.3(4) . . ?

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
C7 C2 C3 C4 -1.8(7) . . . . ?
C1 C2 C3 C4 178.5(5) . . . . ?
C2 C3 C4 C5 0.8(8) . . . . ?
C3 C4 C5 C6 1.0(7) . . . . ?
C3 C4 C5 N1 -178.8(4) . . . . ?
C4 C5 C6 C7 -1.7(7) . . . . ?
N1 C5 C6 C7 178.1(4) . . . . ?
C5 C6 C7 C2 0.7(7) . . . . ?
C3 C2 C7 C6 1.0(7) . . . . ?
C1 C2 C7 C6 -179.2(5) . . . . ?
C13 C8 C9 C10 -3.3(8) . . . . ?
N1 C8 C9 C10 179.5(5) . . . . ?
C8 C9 C10 C11 1.1(9) . . . . ?
C9 C10 C11 C12 2.1(9) . . . . ?
C9 C10 C11 C14 -175.5(5) . . . . ?
C10 C11 C12 C13 -3.3(9) . . . . ?
C14 C11 C12 C13 174.3(6) . . . . ?
C9 C8 C13 C12 2.2(8) . . . . ?
N1 C8 C13 C12 179.4(5) . . . . ?
C11 C12 C13 C8 1.1(9) . . . . ?
C20 C15 C16 C17 0.0 . . . . ?
N1 C15 C16 C17 -175.7(7) . . . . ?
C15 C16 C17 C18 0.0 . . . . ?
C16 C17 C18 C19 0.0 . . . . ?
C16 C17 C18 C29 -176.4(9) . . . . ?
C17 C18 C19 C20 0.0 . . . . ?
C29 C18 C19 C20 177.7(6) . . . . ?
C17 C18 C19 C24 -176.7(7) . . . . ?
C29 C18 C19 C24 1.0(7) . . . . ?
C18 C19 C20 C15 0.0 . . . . ?
C24 C19 C20 C15 176.6(8) . . . . ?
C18 C19 C20 C21 -176.2(10) . . . . ?
C24 C19 C20 C21 0.4(11) . . . . ?
C16 C15 C20 C19 0.0 . . . . ?
N1 C15 C20 C19 174.8(8) . . . . ?
C16 C15 C20 C21 176.2(10) . . . . ?
N1 C15 C20 C21 -9.0(12) . . . . ?
C19 C20 C21 C22 0(2) . . . . ?
C15 C20 C21 C22 -175.8(13) . . . . ?
C20 C21 C22 C23 -1(3) . . . . ?
C21 C22 C23 C24 1(2) . . . . ?
C22 C23 C24 C30 175.7(14) . . . . ?
C22 C23 C24 C19 -0.5(17) . . . . ?
C20 C19 C24 C23 -0.4(12) . . . . ?
C18 C19 C24 C23 176.3(7) . . . . ?
C20 C19 C24 C30 -177.9(6) . . . . ?
C18 C19 C24 C30 -1.3(9) . . . . ?
C30 C25 C26 C27 0.0 . . . . ?
C25 C26 C27 C28 0.0 . . . . ?
C26 C27 C28 C29 0.0 . . . . ?
C27 C28 C29 C30 0.0 . . . . ?
C27 C28 C29 C18 177.9(7) . . . . ?
C17 C18 C29 C30 176.5(6) . . . . ?
C19 C18 C29 C30 -0.4(4) . . . . ?
C17 C18 C29 C28 -1.6(10) . . . . ?
C19 C18 C29 C28 -178.4(5) . . . . ?
C28 C29 C30 C25 0.0 . . . . ?
C18 C29 C30 C25 -178.3(6) . . . . ?
C28 C29 C30 C24 177.9(7) . . . . ?
C18 C29 C30 C24 -0.4(7) . . . . ?
C26 C25 C30 C29 0.0 . . . . ?
C26 C25 C30 C24 -177.5(8) . . . . ?
C23 C24 C30 C29 -175.6(13) . . . . ?
C19 C24 C30 C29 0.9(8) . . . . ?
C23 C24 C30 C25 2.0(18) . . . . ?
C19 C24 C30 C25 178.6(5) . . . . ?
C13 C8 N1 C5 141.6(5) . . . . ?
C9 C8 N1 C5 -41.3(7) . . . . ?
C13 C8 N1 C15 -39.6(7) . . . . ?
C9 C8 N1 C15 137.6(5) . . . . ?
C6 C5 N1 C8 143.2(5) . . . . ?
C4 C5 N1 C8 -37.0(7) . . . . ?
C6 C5 N1 C15 -35.5(8) . . . . ?
C4 C5 N1 C15 144.3(5) . . . . ?
C16 C15 N1 C8 -45.9(5) . . . . ?
C20 C15 N1 C8 138.9(5) . . . . ?
C16 C15 N1 C5 132.9(5) . . . . ?
C20 C15 N1 C5 -42.3(9) . . . . ?

_refine_diff_density_max         1.039
_refine_diff_density_min         -0.543
_refine_diff_density_rms         0.076

####################################################################### 
# 
# 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_mo_170523l_0m
_database_code_depnum_ccdc_archive 'CCDC 1589261'
_audit_update_record             
;
2017-12-05 deposited with the CCDC.
2018-02-02 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            'C46 H34 N4 O4'
_chemical_formula_weight         706.77

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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

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

_cell_length_a                   14.1565(18)
_cell_length_b                   17.917(2)
_cell_length_c                   14.4208(18)
_cell_angle_alpha                90
_cell_angle_beta                 99.826(2)
_cell_angle_gamma                90
_cell_volume                     3604.1(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.303
_exptl_crystal_F_000             1480
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.084
_shelx_estimated_absorpt_T_min   0.990
_shelx_estimated_absorpt_T_max   0.992
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            25692
_diffrn_reflns_av_unetI/netI     0.0416
_diffrn_reflns_av_R_equivalents  0.0411
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.829
_diffrn_reflns_theta_max         25.497
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             6686
_reflns_number_gt                4605
_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)+(0.0901P)²+2.4244P] 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         6686
_refine_ls_number_parameters     574
_refine_ls_number_restraints     46
_refine_ls_R_factor_all          0.0899
_refine_ls_R_factor_gt           0.0569
_refine_ls_wR_factor_ref         0.1833
_refine_ls_wR_factor_gt          0.1487
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.055
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.8728(2) 1.05369(15) 0.1577(2) 0.0492(7) Uani 1 1 d . . . . .
C2 C 0.87732(17) 1.02709(15) 0.2477(2) 0.0426(6) Uani 1 1 d . . . . .
H2 H 0.8918 1.0600 0.2999 0.051 Uiso 1 1 calc R U . . .
C3 C 0.86060(18) 0.95211(15) 0.2623(2) 0.0410(6) Uani 1 1 d . . . . .
H3 H 0.8644 0.9341 0.3247 0.049 Uiso 1 1 calc R U . . .
C4 C 0.83839(18) 0.90289(14) 0.18754(19) 0.0402(6) Uani 1 1 d . . . . .
C5 C 0.8324(2) 0.93072(15) 0.0974(2) 0.0529(8) Uani 1 1 d . . . . .
H5 H 0.8160 0.8983 0.0450 0.063 Uiso 1 1 calc R U . . .
C6 C 0.8500(3) 1.00503(16) 0.0826(2) 0.0604(9) Uani 1 1 d . . . . .
H6 H 0.8465 1.0231 0.0202 0.072 Uiso 1 1 calc R U . . .
C7 C 0.81320(19) 0.70640(14) 0.11785(18) 0.0393(6) Uani 1 1 d . . . . .
H7 H 0.7522 0.6975 0.1347 0.047 Uiso 1 1 calc R U . . .
C8 C 0.86296(18) 0.77177(14) 0.14727(19) 0.0399(6) Uani 1 1 d . . . . .
C9 C 0.8520(2) 0.65452(17) 0.06446(19) 0.0468(7) Uani 1 1 d . . . . .
H9 H 0.8189 0.6093 0.0466 0.056 Uiso 1 1 calc R U . . .
C10 C 0.9395(2) 0.66849(19) 0.0369(2) 0.0552(8) Uani 1 1 d D . . . .
C11 C 0.9886(2) 0.73413(19) 0.0646(2) 0.0562(8) Uani 1 1 d . . . . .
H11 H 1.0482 0.7442 0.0452 0.067 Uiso 1 1 calc R U . . .
C12 C 0.9506(2) 0.78448(16) 0.1202(2) 0.0498(7) Uani 1 1 d . . . . .
H12 H 0.9852 0.8287 0.1404 0.060 Uiso 1 1 calc R U . . .
C13 C 0.76806(18) 0.80367(15) 0.27086(19) 0.0399(6) Uani 1 1 d . . . . .
C14 C 0.69271(18) 0.84852(14) 0.28968(19) 0.0396(6) Uani 1 1 d . . . . .
H14 H 0.6773 0.8937 0.2561 0.047 Uiso 1 1 calc R U . . .
C15 C 0.64105(17) 0.82597(14) 0.35793(18) 0.0363(6) Uani 1 1 d . . . . .
C16 C 0.56085(17) 0.86261(13) 0.39317(18) 0.0350(6) Uani 1 1 d . . . . .
C17 C 0.51069(18) 0.92764(14) 0.37193(19) 0.0399(6) Uani 1 1 d . . . . .
H17 H 0.5267 0.9611 0.3259 0.048 Uiso 1 1 calc R U . . .
C18 C 0.43441(18) 0.94336(13) 0.42064(19) 0.0371(6) Uani 1 1 d . . . . .
C19 C 0.41135(18) 0.89768(13) 0.49204(18) 0.0359(6) Uani 1 1 d . . . . .
C20 C 0.46609(17) 0.83144(13) 0.51823(17) 0.0347(6) Uani 1 1 d . . . . .
C21 C 0.45600(18) 0.77937(13) 0.59089(17) 0.0345(6) Uani 1 1 d . . . . .
C22 C 0.51098(19) 0.71537(14) 0.59889(17) 0.0372(6) Uani 1 1 d . . . . .
H22 H 0.5022 0.6801 0.6459 0.045 Uiso 1 1 calc R U . . .
C23 C 0.57906(19) 0.69932(14) 0.54167(17) 0.0375(6) Uani 1 1 d . . . . .
H23 H 0.6138 0.6537 0.5487 0.045 Uiso 1 1 calc R U . . .
C24 C 0.59461(18) 0.75088(13) 0.47500(17) 0.0348(6) Uani 1 1 d . . . . .
C25 C 0.66099(17) 0.75803(13) 0.40710(17) 0.0343(6) Uani 1 1 d . . . . .
C26 C 0.73429(19) 0.71377(14) 0.38727(18) 0.0386(6) Uani 1 1 d . . . . .
H26 H 0.7479 0.6676 0.4191 0.046 Uiso 1 1 calc R U . . .
C27 C 0.78822(19) 0.73665(14) 0.32088(18) 0.0404(6) Uani 1 1 d . . . . .
H27 H 0.8399 0.7064 0.3089 0.049 Uiso 1 1 calc R U . . .
C28 C 0.53672(17) 0.81583(13) 0.46471(17) 0.0340(6) Uani 1 1 d . . . . .
C29 C 0.3771(2) 1.00884(15) 0.3945(2) 0.0434(6) Uani 1 1 d . . . . .
C30 C 0.3278(2) 0.91814(14) 0.53096(19) 0.0411(6) Uani 1 1 d . . . . .
C31 C 0.42390(17) 0.85290(13) 0.72353(17) 0.0330(5) Uani 1 1 d . . . . .
C32 C 0.35575(18) 0.89566(14) 0.75879(18) 0.0363(6) Uani 1 1 d . . . . .
H32 H 0.2896 0.8845 0.7405 0.044 Uiso 1 1 calc R U . . .
C33 C 0.38319(18) 0.95386(14) 0.81976(18) 0.0363(6) Uani 1 1 d . . . . .
H33 H 0.3361 0.9824 0.8436 0.044 Uiso 1 1 calc R U . . .
C34 C 0.48042(17) 0.97099(13) 0.84666(17) 0.0334(5) Uani 1 1 d . . . . .
C35 C 0.54824(17) 0.92771(13) 0.81386(17) 0.0344(6) Uani 1 1 d . . . . .
H35 H 0.6145 0.9383 0.8330 0.041 Uiso 1 1 calc R U . . .
C36 C 0.52000(17) 0.86867(13) 0.75298(17) 0.0337(5) Uani 1 1 d . . . . .
H36 H 0.5672 0.8388 0.7313 0.040 Uiso 1 1 calc R U . . .
C43 C 0.9228(3) 1.17586(17) 0.2110(3) 0.0726(11) Uani 1 1 d . . . . .
H43A H 0.8733 1.1820 0.2503 0.109 Uiso 1 1 calc R U . . .
H43B H 0.9376 1.2245 0.1858 0.109 Uiso 1 1 calc R U . . .
H43C H 0.9808 1.1550 0.2489 0.109 Uiso 1 1 calc R U . . .
C44 C 0.59905(19) 1.04746(15) 0.9363(2) 0.0446(7) Uani 1 1 d . . . . .
H44A H 0.6292 1.0038 0.9700 0.067 Uiso 1 1 calc R U . . .
H44B H 0.6051 1.0904 0.9789 0.067 Uiso 1 1 calc R U . . .
H44C H 0.6308 1.0586 0.8826 0.067 Uiso 1 1 calc R U . . .
C37 C 0.3261(6) 0.7422(5) 0.6831(6) 0.025(3) Uani 0.501(9) 1 d DG . P A 1
C38 C 0.3213(5) 0.7258(4) 0.7764(5) 0.035(2) Uani 0.501(9) 1 d DG . P A 1
H38 H 0.3610 0.7519 0.8257 0.041 Uiso 0.501(9) 1 calc R U P A 1
C39 C 0.2585(5) 0.6712(3) 0.7976(4) 0.0321(17) Uani 0.501(9) 1 d DG . P A 1
H39 H 0.2553 0.6600 0.8614 0.039 Uiso 0.501(9) 1 calc R U P A 1
C40 C 0.2005(5) 0.6331(3) 0.7255(5) 0.040(2) Uani 0.501(9) 1 d DG . P A 1
C41 C 0.2052(5) 0.6495(4) 0.6322(5) 0.041(3) Uani 0.501(9) 1 d DG . P A 1
H41 H 0.1656 0.6234 0.5829 0.049 Uiso 0.501(9) 1 calc R U P A 1
C42 C 0.2680(6) 0.7040(5) 0.6110(5) 0.031(2) Uani 0.501(9) 1 d DG . P A 1
H42 H 0.2713 0.7152 0.5472 0.038 Uiso 0.501(9) 1 calc R U P A 1
C46 C 0.1173(5) 0.5137(3) 0.7017(7) 0.073(3) Uani 0.501(9) 1 d D . P A 1
H46A H 0.0672 0.5226 0.6469 0.109 Uiso 0.501(9) 1 calc R U P A 1
H46B H 0.0938 0.4782 0.7442 0.109 Uiso 0.501(9) 1 calc R U P A 1
H46C H 0.1743 0.4932 0.6809 0.109 Uiso 0.501(9) 1 calc R U P A 1
O4 O 0.1404(5) 0.5801(3) 0.7484(6) 0.077(3) Uani 0.501(9) 1 d D . P A 1
C37' C 0.3261(8) 0.7388(6) 0.6616(10) 0.036(3) Uani 0.499(9) 1 d D . P A 2
C38' C 0.3204(7) 0.7091(6) 0.7492(8) 0.041(2) Uani 0.499(9) 1 d D . P A 2
H38' H 0.3624 0.7259 0.8037 0.049 Uiso 0.499(9) 1 calc R U P A 2
C39' C 0.2523(7) 0.6544(6) 0.7561(8) 0.053(2) Uani 0.499(9) 1 d D . P A 2
H39' H 0.2466 0.6338 0.8156 0.064 Uiso 0.499(9) 1 calc R U P A 2
C40' C 0.1925(6) 0.6304(5) 0.6749(10) 0.053(4) Uani 0.499(9) 1 d D . P A 2
C41' C 0.1991(8) 0.6624(6) 0.5893(7) 0.051(3) Uani 0.499(9) 1 d D . P A 2
H41' H 0.1575 0.6460 0.5343 0.062 Uiso 0.499(9) 1 calc R U P A 2
C42' C 0.2632(8) 0.7160(7) 0.5824(8) 0.040(2) Uani 0.499(9) 1 d D . P A 2
H42' H 0.2655 0.7385 0.5232 0.048 Uiso 0.499(9) 1 calc R U P A 2
C46' C 0.1209(7) 0.5530(7) 0.7748(9) 0.122(6) Uani 0.499(9) 1 d D U P A 2
H46D H 0.1808 0.5282 0.8026 0.182 Uiso 0.499(9) 1 calc R U P A 2
H46E H 0.0670 0.5187 0.7750 0.182 Uiso 0.499(9) 1 calc R U P A 2
H46F H 0.1118 0.5976 0.8116 0.182 Uiso 0.499(9) 1 calc R U P A 2
O4' O 0.1260(4) 0.5758(4) 0.6730(7) 0.090(3) Uani 0.499(9) 1 d D U P A 2
C45 C 1.0521(5) 0.6342(7) -0.0546(7) 0.158(5) Uani 0.649(9) 1 d D . P B 1
H45A H 1.0337 0.6726 -0.1028 0.237 Uiso 0.649(9) 1 calc R U P B 1
H45B H 1.0786 0.5910 -0.0829 0.237 Uiso 0.649(9) 1 calc R U P B 1
H45C H 1.1004 0.6544 -0.0041 0.237 Uiso 0.649(9) 1 calc R U P B 1
O3 O 0.9684(5) 0.6114(4) -0.0163(5) 0.083(3) Uani 0.649(9) 1 d D U P B 1
C45' C 0.9797(7) 0.5424(5) -0.0071(6) 0.054(3) Uani 0.351(9) 1 d D U P B -2
H45D H 0.9889 0.5302 0.0601 0.081 Uiso 0.351(9) 1 calc R U P B -2
H45E H 1.0288 0.5170 -0.0360 0.081 Uiso 0.351(9) 1 calc R U P B -2
H45F H 0.9160 0.5258 -0.0377 0.081 Uiso 0.351(9) 1 calc R U P B -2
O3' O 0.9881(10) 0.6248(4) -0.0191(10) 0.087(6) Uani 0.351(9) 1 d D . P B -2
N1 N 0.33194(18) 1.06113(14) 0.3733(2) 0.0571(7) Uani 1 1 d . . . . .
N2 N 0.2591(2) 0.93889(15) 0.55474(19) 0.0595(7) Uani 1 1 d . . . . .
N3 N 0.82226(16) 0.82569(12) 0.20227(17) 0.0440(6) Uani 1 1 d . . . . .
N4 N 0.39324(15) 0.79633(11) 0.65530(15) 0.0351(5) Uani 1 1 d D . . . .
O1 O 0.8887(2) 1.12648(11) 0.13507(17) 0.0737(7) Uani 1 1 d . . . . .
O2 O 0.49981(12) 1.03230(9) 0.90333(13) 0.0391(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
C1 O1 1.372(3) . ?
C1 C2 1.375(4) . ?
C1 C6 1.385(4) . ?
C2 C3 1.386(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.386(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.382(4) . ?
C4 N3 1.424(3) . ?
C5 C6 1.378(4) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C9 1.380(4) . ?
C7 C8 1.395(4) . ?
C7 H7 0.9500 . ?
C8 C12 1.382(4) . ?
C8 N3 1.432(4) . ?
C9 C10 1.386(4) . ?
C9 H9 0.9500 . ?
C10 O3 1.381(5) . ?
C10 O3' 1.389(9) . ?
C10 C11 1.390(5) . ?
C11 C12 1.376(4) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 C14 1.399(4) . ?
C13 C27 1.405(4) . ?
C13 N3 1.408(3) . ?
C14 C15 1.383(4) . ?
C14 H14 0.9500 . ?
C15 C25 1.413(3) . ?
C15 C16 1.475(4) . ?
C16 C17 1.372(4) . ?
C16 C28 1.416(3) . ?
C17 C18 1.413(4) . ?
C17 H17 0.9500 . ?
C18 C19 1.397(4) . ?
C18 C29 1.439(4) . ?
C19 C20 1.432(3) . ?
C19 C30 1.440(4) . ?
C20 C28 1.392(4) . ?
C20 C21 1.428(3) . ?
C21 C22 1.379(3) . ?
C21 N4 1.423(3) . ?
C22 C23 1.401(4) . ?
C22 H22 0.9500 . ?
C23 C24 1.378(4) . ?
C23 H23 0.9500 . ?
C24 C28 1.416(3) . ?
C24 C25 1.474(4) . ?
C25 C26 1.374(4) . ?
C26 C27 1.384(4) . ?
C26 H26 0.9500 . ?
C27 H27 0.9500 . ?
C29 N1 1.146(3) . ?
C30 N2 1.147(4) . ?
C31 C36 1.383(3) . ?
C31 C32 1.394(4) . ?
C31 N4 1.428(3) . ?
C32 C33 1.376(4) . ?
C32 H32 0.9500 . ?
C33 C34 1.399(3) . ?
C33 H33 0.9500 . ?
C34 O2 1.369(3) . ?
C34 C35 1.379(3) . ?
C35 C36 1.389(3) . ?
C35 H35 0.9500 . ?
C36 H36 0.9500 . ?
C43 O1 1.426(4) . ?
C43 H43A 0.9800 . ?
C43 H43B 0.9800 . ?
C43 H43C 0.9800 . ?
C44 O2 1.430(3) . ?
C44 H44A 0.9800 . ?
C44 H44B 0.9800 . ?
C44 H44C 0.9800 . ?
C37 C38 1.3900 . ?
C37 C42 1.3900 . ?
C37 N4 1.462(4) . ?
C38 C39 1.3900 . ?
C38 H38 0.9500 . ?
C39 C40 1.3900 . ?
C39 H39 0.9500 . ?
C40 O4 1.352(6) . ?
C40 C41 1.3900 . ?
C41 C42 1.3900 . ?
C41 H41 0.9500 . ?
C42 H42 0.9500 . ?
C46 O4 1.378(8) . ?
C46 H46A 0.9800 . ?
C46 H46B 0.9800 . ?
C46 H46C 0.9800 . ?
C37' C38' 1.385(10) . ?
C37' C42' 1.385(11) . ?
C37' N4 1.416(7) . ?
C38' C39' 1.390(10) . ?
C38' H38' 0.9500 . ?
C39' C40' 1.391(11) . ?
C39' H39' 0.9500 . ?
C40' O4' 1.353(9) . ?
C40' C41' 1.379(11) . ?
C41' C42' 1.336(12) . ?
C41' H41' 0.9500 . ?
C42' H42' 0.9500 . ?
C46' O4' 1.537(13) . ?
C46' H46D 0.9800 . ?
C46' H46E 0.9800 . ?
C46' H46F 0.9800 . ?
C45 O3 1.449(7) . ?
C45 H45A 0.9800 . ?
C45 H45B 0.9800 . ?
C45 H45C 0.9800 . ?
C45' O3' 1.494(8) . ?
C45' H45D 0.9800 . ?
C45' H45E 0.9800 . ?
C45' H45F 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
O1 C1 C2 124.8(3) . . ?
O1 C1 C6 116.0(3) . . ?
C2 C1 C6 119.2(3) . . ?
C1 C2 C3 119.8(3) . . ?
C1 C2 H2 120.1 . . ?
C3 C2 H2 120.1 . . ?
C4 C3 C2 121.4(3) . . ?
C4 C3 H3 119.3 . . ?
C2 C3 H3 119.3 . . ?
C5 C4 C3 118.1(2) . . ?
C5 C4 N3 120.4(2) . . ?
C3 C4 N3 121.5(2) . . ?
C6 C5 C4 120.7(3) . . ?
C6 C5 H5 119.6 . . ?
C4 C5 H5 119.6 . . ?
C5 C6 C1 120.8(3) . . ?
C5 C6 H6 119.6 . . ?
C1 C6 H6 119.6 . . ?
C9 C7 C8 120.4(3) . . ?
C9 C7 H7 119.8 . . ?
C8 C7 H7 119.8 . . ?
C12 C8 C7 118.9(3) . . ?
C12 C8 N3 120.7(2) . . ?
C7 C8 N3 120.3(2) . . ?
C7 C9 C10 119.9(3) . . ?
C7 C9 H9 120.0 . . ?
C10 C9 H9 120.0 . . ?
O3 C10 C9 112.9(4) . . ?
C9 C10 O3' 128.4(5) . . ?
O3 C10 C11 127.2(4) . . ?
C9 C10 C11 119.9(3) . . ?
O3' C10 C11 111.7(5) . . ?
C12 C11 C10 119.7(3) . . ?
C12 C11 H11 120.1 . . ?
C10 C11 H11 120.1 . . ?
C11 C12 C8 121.0(3) . . ?
C11 C12 H12 119.5 . . ?
C8 C12 H12 119.5 . . ?
C14 C13 C27 119.1(2) . . ?
C14 C13 N3 120.0(2) . . ?
C27 C13 N3 120.9(2) . . ?
C15 C14 C13 118.9(2) . . ?
C15 C14 H14 120.5 . . ?
C13 C14 H14 120.5 . . ?
C14 C15 C25 121.6(2) . . ?
C14 C15 C16 130.3(2) . . ?
C25 C15 C16 108.1(2) . . ?
C17 C16 C28 119.1(2) . . ?
C17 C16 C15 134.5(2) . . ?
C28 C16 C15 106.4(2) . . ?
C16 C17 C18 118.0(2) . . ?
C16 C17 H17 121.0 . . ?
C18 C17 H17 121.0 . . ?
C19 C18 C17 123.0(2) . . ?
C19 C18 C29 118.6(2) . . ?
C17 C18 C29 118.5(2) . . ?
C18 C19 C20 119.7(2) . . ?
C18 C19 C30 116.7(2) . . ?
C20 C19 C30 123.5(2) . . ?
C28 C20 C21 116.5(2) . . ?
C28 C20 C19 115.3(2) . . ?
C21 C20 C19 128.1(2) . . ?
C22 C21 N4 121.9(2) . . ?
C22 C21 C20 118.6(2) . . ?
N4 C21 C20 119.4(2) . . ?
C21 C22 C23 123.8(2) . . ?
C21 C22 H22 118.1 . . ?
C23 C22 H22 118.1 . . ?
C24 C23 C22 118.8(2) . . ?
C24 C23 H23 120.6 . . ?
C22 C23 H23 120.6 . . ?
C23 C24 C28 117.7(2) . . ?
C23 C24 C25 135.9(2) . . ?
C28 C24 C25 106.4(2) . . ?
C26 C25 C15 119.1(2) . . ?
C26 C25 C24 132.7(2) . . ?
C15 C25 C24 108.2(2) . . ?
C25 C26 C27 119.9(2) . . ?
C25 C26 H26 120.1 . . ?
C27 C26 H26 120.1 . . ?
C26 C27 C13 121.4(3) . . ?
C26 C27 H27 119.3 . . ?
C13 C27 H27 119.3 . . ?
C20 C28 C16 124.8(2) . . ?
C20 C28 C24 124.4(2) . . ?
C16 C28 C24 110.8(2) . . ?
N1 C29 C18 179.5(3) . . ?
N2 C30 C19 173.5(3) . . ?
C36 C31 C32 118.8(2) . . ?
C36 C31 N4 121.6(2) . . ?
C32 C31 N4 119.6(2) . . ?
C33 C32 C31 120.8(2) . . ?
C33 C32 H32 119.6 . . ?
C31 C32 H32 119.6 . . ?
C32 C33 C34 120.0(2) . . ?
C32 C33 H33 120.0 . . ?
C34 C33 H33 120.0 . . ?
O2 C34 C35 125.1(2) . . ?
O2 C34 C33 115.4(2) . . ?
C35 C34 C33 119.4(2) . . ?
C34 C35 C36 120.2(2) . . ?
C34 C35 H35 119.9 . . ?
C36 C35 H35 119.9 . . ?
C31 C36 C35 120.8(2) . . ?
C31 C36 H36 119.6 . . ?
C35 C36 H36 119.6 . . ?
O1 C43 H43A 109.5 . . ?
O1 C43 H43B 109.5 . . ?
H43A C43 H43B 109.5 . . ?
O1 C43 H43C 109.5 . . ?
H43A C43 H43C 109.5 . . ?
H43B C43 H43C 109.5 . . ?
O2 C44 H44A 109.5 . . ?
O2 C44 H44B 109.5 . . ?
H44A C44 H44B 109.5 . . ?
O2 C44 H44C 109.5 . . ?
H44A C44 H44C 109.5 . . ?
H44B C44 H44C 109.5 . . ?
C38 C37 C42 120.0 . . ?
C38 C37 N4 123.2(5) . . ?
C42 C37 N4 116.8(5) . . ?
C39 C38 C37 120.0 . . ?
C39 C38 H38 120.0 . . ?
C37 C38 H38 120.0 . . ?
C40 C39 C38 120.0 . . ?
C40 C39 H39 120.0 . . ?
C38 C39 H39 120.0 . . ?
O4 C40 C41 121.4(6) . . ?
O4 C40 C39 118.6(6) . . ?
C41 C40 C39 120.0 . . ?
C42 C41 C40 120.0 . . ?
C42 C41 H41 120.0 . . ?
C40 C41 H41 120.0 . . ?
C41 C42 C37 120.0 . . ?
C41 C42 H42 120.0 . . ?
C37 C42 H42 120.0 . . ?
O4 C46 H46A 109.5 . . ?
O4 C46 H46B 109.5 . . ?
H46A C46 H46B 109.5 . . ?
O4 C46 H46C 109.5 . . ?
H46A C46 H46C 109.5 . . ?
H46B C46 H46C 109.5 . . ?
C40 O4 C46 126.4(6) . . ?
C38' C37' C42' 120.6(7) . . ?
C38' C37' N4 118.8(9) . . ?
C42' C37' N4 120.4(10) . . ?
C37' C38' C39' 119.0(8) . . ?
C37' C38' H38' 120.5 . . ?
C39' C38' H38' 120.5 . . ?
C38' C39' C40' 119.2(7) . . ?
C38' C39' H39' 120.4 . . ?
C40' C39' H39' 120.4 . . ?
O4' C40' C41' 115.8(10) . . ?
O4' C40' C39' 124.2(9) . . ?
C41' C40' C39' 120.0(7) . . ?
C42' C41' C40' 121.1(9) . . ?
C42' C41' H41' 119.5 . . ?
C40' C41' H41' 119.5 . . ?
C41' C42' C37' 120.0(9) . . ?
C41' C42' H42' 120.0 . . ?
C37' C42' H42' 120.0 . . ?
O4' C46' H46D 109.5 . . ?
O4' C46' H46E 109.5 . . ?
H46D C46' H46E 109.5 . . ?
O4' C46' H46F 109.5 . . ?
H46D C46' H46F 109.5 . . ?
H46E C46' H46F 109.5 . . ?
C40' O4' C46' 108.5(8) . . ?
O3 C45 H45A 109.5 . . ?
O3 C45 H45B 109.5 . . ?
H45A C45 H45B 109.5 . . ?
O3 C45 H45C 109.5 . . ?
H45A C45 H45C 109.5 . . ?
H45B C45 H45C 109.5 . . ?
C10 O3 C45 110.0(6) . . ?
O3' C45' H45D 109.5 . . ?
O3' C45' H45E 109.5 . . ?
H45D C45' H45E 109.5 . . ?
O3' C45' H45F 109.5 . . ?
H45D C45' H45F 109.5 . . ?
H45E C45' H45F 109.5 . . ?
C10 O3' C45' 115.7(7) . . ?
C13 N3 C4 119.8(2) . . ?
C13 N3 C8 121.3(2) . . ?
C4 N3 C8 118.9(2) . . ?
C37' N4 C21 112.8(6) . . ?
C37' N4 C31 127.0(6) . . ?
C21 N4 C31 116.8(2) . . ?
C21 N4 C37 123.0(4) . . ?
C31 N4 C37 114.7(4) . . ?
C1 O1 C43 117.1(3) . . ?
C34 O2 C44 115.88(19) . . ?

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
O1 C1 C2 C3 -179.5(3) . . . . ?
C6 C1 C2 C3 1.1(4) . . . . ?
C1 C2 C3 C4 -0.6(4) . . . . ?
C2 C3 C4 C5 -0.6(4) . . . . ?
C2 C3 C4 N3 179.3(2) . . . . ?
C3 C4 C5 C6 1.3(5) . . . . ?
N3 C4 C5 C6 -178.6(3) . . . . ?
C4 C5 C6 C1 -0.8(5) . . . . ?
O1 C1 C6 C5 -179.8(3) . . . . ?
C2 C1 C6 C5 -0.4(5) . . . . ?
C9 C7 C8 C12 1.5(4) . . . . ?
C9 C7 C8 N3 179.7(2) . . . . ?
C8 C7 C9 C10 -2.3(4) . . . . ?
C7 C9 C10 O3 -179.8(4) . . . . ?
C7 C9 C10 O3' -177.6(9) . . . . ?
C7 C9 C10 C11 1.2(4) . . . . ?
O3 C10 C11 C12 -178.0(5) . . . . ?
C9 C10 C11 C12 0.8(5) . . . . ?
O3' C10 C11 C12 179.8(8) . . . . ?
C10 C11 C12 C8 -1.6(5) . . . . ?
C7 C8 C12 C11 0.5(4) . . . . ?
N3 C8 C12 C11 -177.7(3) . . . . ?
C27 C13 C14 C15 0.8(4) . . . . ?
N3 C13 C14 C15 -179.5(2) . . . . ?
C13 C14 C15 C25 -1.7(4) . . . . ?
C13 C14 C15 C16 178.4(2) . . . . ?
C14 C15 C16 C17 0.9(5) . . . . ?
C25 C15 C16 C17 -179.1(3) . . . . ?
C14 C15 C16 C28 -178.6(2) . . . . ?
C25 C15 C16 C28 1.5(3) . . . . ?
C28 C16 C17 C18 -2.3(4) . . . . ?
C15 C16 C17 C18 178.3(2) . . . . ?
C16 C17 C18 C19 3.2(4) . . . . ?
C16 C17 C18 C29 -175.9(2) . . . . ?
C17 C18 C19 C20 -0.2(4) . . . . ?
C29 C18 C19 C20 178.9(2) . . . . ?
C17 C18 C19 C30 -176.0(2) . . . . ?
C29 C18 C19 C30 3.1(3) . . . . ?
C18 C19 C20 C28 -3.4(3) . . . . ?
C30 C19 C20 C28 172.0(2) . . . . ?
C18 C19 C20 C21 177.7(2) . . . . ?
C30 C19 C20 C21 -6.9(4) . . . . ?
C28 C20 C21 C22 -4.6(3) . . . . ?
C19 C20 C21 C22 174.3(2) . . . . ?
C28 C20 C21 N4 172.6(2) . . . . ?
C19 C20 C21 N4 -8.5(4) . . . . ?
N4 C21 C22 C23 -174.8(2) . . . . ?
C20 C21 C22 C23 2.2(4) . . . . ?
C21 C22 C23 C24 1.9(4) . . . . ?
C22 C23 C24 C28 -3.4(3) . . . . ?
C22 C23 C24 C25 175.5(3) . . . . ?
C14 C15 C25 C26 0.8(4) . . . . ?
C16 C15 C25 C26 -179.3(2) . . . . ?
C14 C15 C25 C24 179.4(2) . . . . ?
C16 C15 C25 C24 -0.6(3) . . . . ?
C23 C24 C25 C26 -1.0(5) . . . . ?
C28 C24 C25 C26 178.0(3) . . . . ?
C23 C24 C25 C15 -179.4(3) . . . . ?
C28 C24 C25 C15 -0.4(3) . . . . ?
C15 C25 C26 C27 1.0(4) . . . . ?
C24 C25 C26 C27 -177.3(2) . . . . ?
C25 C26 C27 C13 -1.8(4) . . . . ?
C14 C13 C27 C26 0.9(4) . . . . ?
N3 C13 C27 C26 -178.8(2) . . . . ?
C21 C20 C28 C16 -176.5(2) . . . . ?
C19 C20 C28 C16 4.5(3) . . . . ?
C21 C20 C28 C24 3.2(3) . . . . ?
C19 C20 C28 C24 -175.9(2) . . . . ?
C17 C16 C28 C20 -1.6(4) . . . . ?
C15 C16 C28 C20 177.9(2) . . . . ?
C17 C16 C28 C24 178.7(2) . . . . ?
C15 C16 C28 C24 -1.8(3) . . . . ?
C23 C24 C28 C20 0.8(3) . . . . ?
C25 C24 C28 C20 -178.3(2) . . . . ?
C23 C24 C28 C16 -179.4(2) . . . . ?
C25 C24 C28 C16 1.4(3) . . . . ?
C36 C31 C32 C33 1.8(4) . . . . ?
N4 C31 C32 C33 -175.6(2) . . . . ?
C31 C32 C33 C34 0.4(4) . . . . ?
C32 C33 C34 O2 176.6(2) . . . . ?
C32 C33 C34 C35 -2.0(4) . . . . ?
O2 C34 C35 C36 -177.0(2) . . . . ?
C33 C34 C35 C36 1.4(4) . . . . ?
C32 C31 C36 C35 -2.3(4) . . . . ?
N4 C31 C36 C35 175.0(2) . . . . ?
C34 C35 C36 C31 0.7(4) . . . . ?
C42 C37 C38 C39 0.0 . . . . ?
N4 C37 C38 C39 -177.1(9) . . . . ?
C37 C38 C39 C40 0.0 . . . . ?
C38 C39 C40 O4 179.8(7) . . . . ?
C38 C39 C40 C41 0.0 . . . . ?
O4 C40 C41 C42 -179.8(8) . . . . ?
C39 C40 C41 C42 0.0 . . . . ?
C40 C41 C42 C37 0.0 . . . . ?
C38 C37 C42 C41 0.0 . . . . ?
N4 C37 C42 C41 177.3(8) . . . . ?
C41 C40 O4 C46 36.5(13) . . . . ?
C39 C40 O4 C46 -143.3(9) . . . . ?
C42' C37' C38' C39' 1.9(11) . . . . ?
N4 C37' C38' C39' 177.7(10) . . . . ?
C37' C38' C39' C40' 0.7(12) . . . . ?
C38' C39' C40' O4' 177.6(10) . . . . ?
C38' C39' C40' C41' -2.0(14) . . . . ?
O4' C40' C41' C42' -179.0(9) . . . . ?
C39' C40' C41' C42' 0.7(18) . . . . ?
C40' C41' C42' C37' 1.9(16) . . . . ?
C38' C37' C42' C41' -3.2(12) . . . . ?
N4 C37' C42' C41' -179.0(12) . . . . ?
C41' C40' O4' C46' -173.8(10) . . . . ?
C39' C40' O4' C46' 6.5(13) . . . . ?
C9 C10 O3 C45 171.3(6) . . . . ?
C11 C10 O3 C45 -9.8(9) . . . . ?
C9 C10 O3' C45' -35.8(17) . . . . ?
C11 C10 O3' C45' 145.3(9) . . . . ?
C14 C13 N3 C4 32.8(4) . . . . ?
C27 C13 N3 C4 -147.5(2) . . . . ?
C14 C13 N3 C8 -148.0(2) . . . . ?
C27 C13 N3 C8 31.7(4) . . . . ?
C5 C4 N3 C13 -138.2(3) . . . . ?
C3 C4 N3 C13 42.0(4) . . . . ?
C5 C4 N3 C8 42.6(4) . . . . ?
C3 C4 N3 C8 -137.2(3) . . . . ?
C12 C8 N3 C13 -145.1(3) . . . . ?
C7 C8 N3 C13 36.7(4) . . . . ?
C12 C8 N3 C4 34.1(4) . . . . ?
C7 C8 N3 C4 -144.1(2) . . . . ?
C38' C37' N4 C21 125.3(8) . . . . ?
C42' C37' N4 C21 -58.8(9) . . . . ?
C38' C37' N4 C31 -32.9(12) . . . . ?
C42' C37' N4 C31 143.0(7) . . . . ?
C22 C21 N4 C37' -55.8(7) . . . . ?
C20 C21 N4 C37' 127.2(6) . . . . ?
C22 C21 N4 C31 104.8(3) . . . . ?
C20 C21 N4 C31 -72.3(3) . . . . ?
C22 C21 N4 C37 -47.7(5) . . . . ?
C20 C21 N4 C37 135.2(5) . . . . ?
C36 C31 N4 C37' 131.3(7) . . . . ?
C32 C31 N4 C37' -51.4(8) . . . . ?
C36 C31 N4 C21 -26.0(3) . . . . ?
C32 C31 N4 C21 151.2(2) . . . . ?
C36 C31 N4 C37 128.7(5) . . . . ?
C32 C31 N4 C37 -54.0(5) . . . . ?
C38 C37 N4 C21 127.5(5) . . . . ?
C42 C37 N4 C21 -49.8(7) . . . . ?
C38 C37 N4 C31 -25.5(8) . . . . ?
C42 C37 N4 C31 157.2(4) . . . . ?
C2 C1 O1 C43 7.4(5) . . . . ?
C6 C1 O1 C43 -173.2(3) . . . . ?
C35 C34 O2 C44 -5.5(3) . . . . ?
C33 C34 O2 C44 176.0(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C41' H41' O1 0.95 2.44 3.325(10) 154.3 2_645
C12 H12 O4' 0.95 2.61 3.517(7) 160.1 4_675
C3 H3 O3 0.95 2.63 3.487(8) 149.8 4_576

_refine_diff_density_max         0.723
_refine_diff_density_min         -0.284
_refine_diff_density_rms         0.049

####################################################################### 
# 
# 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_hkl5
_database_code_depnum_ccdc_archive 'CCDC 1589258'
_audit_update_record             
;
2017-12-05 deposited with the CCDC.
2018-02-02 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            'C46 H34 N4'
_chemical_formula_weight         642.77

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                   11.856(7)
_cell_length_b                   12.147(7)
_cell_length_c                   13.446(8)
_cell_angle_alpha                102.687(8)
_cell_angle_beta                 111.422(8)
_cell_angle_gamma                93.005(9)
_cell_volume                     1739.7(17)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    1793
_cell_measurement_theta_min      2.71
_cell_measurement_theta_max      22.88

_exptl_crystal_description       needle
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.227
_exptl_crystal_F_000             676
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    0.072
_shelx_estimated_absorpt_T_min   0.989
_shelx_estimated_absorpt_T_max   0.999
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(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            5978
_diffrn_reflns_av_unetI/netI     0.0957
_diffrn_reflns_av_R_equivalents  0.0557
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.683
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measured_fraction_theta_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_point_group_measured_fraction_full 0.986
_reflns_number_total             5978
_reflns_number_gt                3309
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 _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-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
; 
 Refined as a 2-component twin. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1289P)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     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.010(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         5978
_refine_ls_number_parameters     457
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1331
_refine_ls_R_factor_gt           0.0712
_refine_ls_wR_factor_ref         0.2394
_refine_ls_wR_factor_gt          0.1970
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.030
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.2052(6) 0.3276(5) -0.6230(5) 0.0959(19) Uani 1 1 d . . . . .
H1A H 0.2196 0.4093 -0.5971 0.144 Uiso 1 1 calc R U . . .
H1B H 0.1190 0.3013 -0.6514 0.144 Uiso 1 1 calc R U . . .
H1C H 0.2353 0.3049 -0.6807 0.144 Uiso 1 1 calc R U . . .
C2 C 0.2709(4) 0.2766(4) -0.5291(4) 0.0563(12) Uani 1 1 d . . . . .
C3 C 0.3819(4) 0.3290(4) -0.4450(4) 0.0596(12) Uani 1 1 d . . . . .
H3 H 0.4175 0.3982 -0.4469 0.072 Uiso 1 1 calc R U . . .
C4 C 0.4407(4) 0.2828(3) -0.3596(3) 0.0524(11) Uani 1 1 d . . . . .
H4 H 0.5155 0.3205 -0.3054 0.063 Uiso 1 1 calc R U . . .
C5 C 0.3912(4) 0.1813(3) -0.3522(3) 0.0433(10) Uani 1 1 d . . . . .
C6 C 0.2795(4) 0.1271(3) -0.4361(3) 0.0481(10) Uani 1 1 d . . . . .
H6 H 0.2435 0.0584 -0.4336 0.058 Uiso 1 1 calc R U . . .
C7 C 0.2221(4) 0.1743(4) -0.5228(3) 0.0530(11) Uani 1 1 d . . . . .
H7 H 0.1486 0.1359 -0.5785 0.064 Uiso 1 1 calc R U . . .
C8 C 0.4625(4) 0.0188(3) -0.2747(3) 0.0471(10) Uani 1 1 d . . . . .
C9 C 0.4854(4) -0.0284(4) -0.1850(4) 0.0640(13) Uani 1 1 d . . . . .
H9 H 0.4953 0.0174 -0.1162 0.077 Uiso 1 1 calc R U . . .
C10 C 0.4935(5) -0.1430(4) -0.1983(4) 0.0727(14) Uani 1 1 d . . . . .
H10 H 0.5099 -0.1730 -0.1373 0.087 Uiso 1 1 calc R U . . .
C11 C 0.4783(5) -0.2147(4) -0.2979(5) 0.0682(14) Uani 1 1 d . . . . .
C12 C 0.4587(4) -0.1659(4) -0.3856(4) 0.0623(13) Uani 1 1 d . . . . .
H12 H 0.4504 -0.2116 -0.4539 0.075 Uiso 1 1 calc R U . . .
C13 C 0.4511(4) -0.0506(3) -0.3740(3) 0.0509(11) Uani 1 1 d . . . . .
H13 H 0.4382 -0.0200 -0.4342 0.061 Uiso 1 1 calc R U . . .
C14 C 0.4827(6) -0.3413(4) -0.3108(6) 0.104(2) Uani 1 1 d . . . . .
H14A H 0.5580 -0.3526 -0.2571 0.156 Uiso 1 1 calc R U . . .
H14B H 0.4782 -0.3763 -0.3837 0.156 Uiso 1 1 calc R U . . .
H14C H 0.4148 -0.3754 -0.2997 0.156 Uiso 1 1 calc R U . . .
C15 C 0.5157(4) 0.2148(3) -0.1574(3) 0.0459(10) Uani 1 1 d . . . . .
C16 C 0.4541(4) 0.2686(3) -0.0970(3) 0.0487(10) Uani 1 1 d . . . . .
H16 H 0.3697 0.2484 -0.1222 0.058 Uiso 1 1 calc R U . . .
C17 C 0.5136(3) 0.3523(3) 0.0007(3) 0.0436(10) Uani 1 1 d . . . . .
H17 H 0.4701 0.3884 0.0404 0.052 Uiso 1 1 calc R U . . .
C18 C 0.6385(3) 0.3809(3) 0.0378(3) 0.0378(9) Uani 1 1 d . . . . .
C19 C 0.7271(3) 0.4672(3) 0.1333(3) 0.0354(9) Uani 1 1 d . . . . .
C20 C 0.7231(4) 0.5466(3) 0.2206(3) 0.0414(9) Uani 1 1 d . . . . .
H20 H 0.6504 0.5505 0.2317 0.050 Uiso 1 1 calc R U . . .
C21 C 0.8285(4) 0.6218(3) 0.2933(3) 0.0432(10) Uani 1 1 d . . . . .
H21 H 0.8233 0.6766 0.3512 0.052 Uiso 1 1 calc R U . . .
C22 C 0.9395(3) 0.6188(3) 0.2832(3) 0.0379(9) Uani 1 1 d . . . . .
C23 C 0.9509(3) 0.5303(3) 0.1984(3) 0.0349(9) Uani 1 1 d . . . . .
C24 C 1.0580(3) 0.5039(3) 0.1807(3) 0.0383(9) Uani 1 1 d . . . . .
C25 C 1.0497(3) 0.4133(3) 0.0919(3) 0.0398(9) Uani 1 1 d . . . . .
C26 C 0.9367(4) 0.3491(3) 0.0165(3) 0.0442(10) Uani 1 1 d . . . . .
H26 H 0.9328 0.2922 -0.0440 0.053 Uiso 1 1 calc R U . . .
C27 C 0.8332(3) 0.3720(3) 0.0339(3) 0.0372(9) Uani 1 1 d . . . . .
C28 C 0.7024(3) 0.3232(3) -0.0228(3) 0.0388(9) Uani 1 1 d . . . . .
C29 C 0.6422(4) 0.2393(3) -0.1196(3) 0.0460(10) Uani 1 1 d . . . . .
H29 H 0.6851 0.2003 -0.1583 0.055 Uiso 1 1 calc R U . . .
C30 C 0.8412(3) 0.4600(3) 0.1254(3) 0.0330(8) Uani 1 1 d . . . . .
C31 C 1.1777(4) 0.5600(4) 0.2551(3) 0.0511(11) Uani 1 1 d . . . . .
C32 C 1.1593(4) 0.3867(4) 0.0749(3) 0.0542(11) Uani 1 1 d . . . . .
C33 C 1.0663(4) 0.7887(3) 0.2964(3) 0.0419(10) Uani 1 1 d . . . . .
C34 C 1.1844(4) 0.8466(3) 0.3360(3) 0.0517(11) Uani 1 1 d . . . . .
H34 H 1.2457 0.8308 0.3956 0.062 Uiso 1 1 calc R U . . .
C35 C 1.2108(4) 0.9267(4) 0.2875(4) 0.0561(12) Uani 1 1 d . . . . .
H35 H 1.2903 0.9650 0.3156 0.067 Uiso 1 1 calc R U . . .
C36 C 1.1234(5) 0.9531(4) 0.1980(4) 0.0594(12) Uani 1 1 d . . . . .
C37 C 1.0065(4) 0.8944(4) 0.1588(3) 0.0569(12) Uani 1 1 d . . . . .
H37 H 0.9457 0.9097 0.0984 0.068 Uiso 1 1 calc R U . . .
C38 C 0.9773(4) 0.8132(3) 0.2072(3) 0.0467(10) Uani 1 1 d . . . . .
H38 H 0.8977 0.7752 0.1795 0.056 Uiso 1 1 calc R U . . .
C39 C 1.1558(6) 1.0406(5) 0.1449(5) 0.101(2) Uani 1 1 d . . . . .
H39A H 1.1813 1.1140 0.1972 0.151 Uiso 1 1 calc R U . . .
H39B H 1.0855 1.0440 0.0816 0.151 Uiso 1 1 calc R U . . .
H39C H 1.2213 1.0195 0.1221 0.151 Uiso 1 1 calc R U . . .
C40 C 1.0724(3) 0.7402(3) 0.4645(3) 0.0414(9) Uani 1 1 d . . . . .
C41 C 1.0798(4) 0.8528(3) 0.5197(3) 0.0469(10) Uani 1 1 d . . . . .
H41 H 1.0618 0.9079 0.4802 0.056 Uiso 1 1 calc R U . . .
C42 C 1.1139(4) 0.8838(3) 0.6331(3) 0.0516(11) Uani 1 1 d . . . . .
H42 H 1.1192 0.9598 0.6689 0.062 Uiso 1 1 calc R U . . .
C43 C 1.1399(4) 0.8049(4) 0.6936(4) 0.0584(12) Uani 1 1 d . . . . .
C44 C 1.1305(5) 0.6934(4) 0.6384(4) 0.0732(14) Uani 1 1 d . . . . .
H44 H 1.1473 0.6386 0.6783 0.088 Uiso 1 1 calc R U . . .
C45 C 1.0969(4) 0.6604(4) 0.5255(4) 0.0596(12) Uani 1 1 d . . . . .
H45 H 1.0908 0.5840 0.4903 0.071 Uiso 1 1 calc R U . . .
C46 C 1.1790(6) 0.8400(5) 0.8175(4) 0.0898(18) Uani 1 1 d . . . . .
H46A H 1.2511 0.8077 0.8514 0.135 Uiso 1 1 calc R U . . .
H46B H 1.1143 0.8130 0.8370 0.135 Uiso 1 1 calc R U . . .
H46C H 1.1965 0.9216 0.8431 0.135 Uiso 1 1 calc R U . . .
N1 N 0.4492(3) 0.1353(3) -0.2616(3) 0.0545(10) Uani 1 1 d . . . . .
N2 N 1.2776(4) 0.5967(4) 0.3108(4) 0.0808(13) Uani 1 1 d . . . . .
N3 N 1.2432(4) 0.3610(4) 0.0582(4) 0.0851(14) Uani 1 1 d . . . . .
N4 N 1.0403(3) 0.7063(3) 0.3489(2) 0.0427(8) 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 C2 1.504(7) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C7 1.376(6) . ?
C2 C3 1.388(6) . ?
C3 C4 1.363(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.377(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.397(5) . ?
C5 N1 1.413(5) . ?
C6 C7 1.381(6) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 C13 1.369(5) . ?
C8 C9 1.392(6) . ?
C8 N1 1.411(5) . ?
C9 C10 1.378(6) . ?
C9 H9 0.9300 . ?
C10 C11 1.370(7) . ?
C10 H10 0.9300 . ?
C11 C12 1.385(7) . ?
C11 C14 1.515(7) . ?
C12 C13 1.387(6) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 C16 1.368(6) . ?
C15 C29 1.388(6) . ?
C15 N1 1.426(5) . ?
C16 C17 1.385(5) . ?
C16 H16 0.9300 . ?
C17 C18 1.376(5) . ?
C17 H17 0.9300 . ?
C18 C28 1.408(5) . ?
C18 C19 1.469(5) . ?
C19 C20 1.362(5) . ?
C19 C30 1.402(5) . ?
C20 C21 1.395(5) . ?
C20 H20 0.9300 . ?
C21 C22 1.372(5) . ?
C21 H21 0.9300 . ?
C22 N4 1.422(4) . ?
C22 C23 1.437(5) . ?
C23 C30 1.402(5) . ?
C23 C24 1.415(5) . ?
C24 C25 1.405(5) . ?
C24 C31 1.428(6) . ?
C25 C26 1.408(5) . ?
C25 C32 1.440(6) . ?
C26 C27 1.361(5) . ?
C26 H26 0.9300 . ?
C27 C30 1.411(5) . ?
C27 C28 1.476(5) . ?
C28 C29 1.381(5) . ?
C29 H29 0.9300 . ?
C31 N2 1.146(5) . ?
C32 N3 1.141(6) . ?
C33 C38 1.381(5) . ?
C33 C34 1.387(5) . ?
C33 N4 1.425(5) . ?
C34 C35 1.367(6) . ?
C34 H34 0.9300 . ?
C35 C36 1.384(7) . ?
C35 H35 0.9300 . ?
C36 C37 1.380(6) . ?
C36 C39 1.509(6) . ?
C37 C38 1.389(6) . ?
C37 H37 0.9300 . ?
C38 H38 0.9300 . ?
C39 H39A 0.9600 . ?
C39 H39B 0.9600 . ?
C39 H39C 0.9600 . ?
C40 C45 1.379(6) . ?
C40 C41 1.387(5) . ?
C40 N4 1.414(5) . ?
C41 C42 1.383(5) . ?
C41 H41 0.9300 . ?
C42 C43 1.366(6) . ?
C42 H42 0.9300 . ?
C43 C44 1.371(7) . ?
C43 C46 1.509(6) . ?
C44 C45 1.379(6) . ?
C44 H44 0.9300 . ?
C45 H45 0.9300 . ?
C46 H46A 0.9600 . ?
C46 H46B 0.9600 . ?
C46 H46C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C7 C2 C3 116.7(4) . . ?
C7 C2 C1 120.8(5) . . ?
C3 C2 C1 122.6(4) . . ?
C4 C3 C2 122.4(4) . . ?
C4 C3 H3 118.8 . . ?
C2 C3 H3 118.8 . . ?
C3 C4 C5 121.1(4) . . ?
C3 C4 H4 119.5 . . ?
C5 C4 H4 119.5 . . ?
C4 C5 C6 117.5(4) . . ?
C4 C5 N1 121.3(3) . . ?
C6 C5 N1 121.2(3) . . ?
C7 C6 C5 120.7(4) . . ?
C7 C6 H6 119.7 . . ?
C5 C6 H6 119.7 . . ?
C2 C7 C6 121.7(4) . . ?
C2 C7 H7 119.1 . . ?
C6 C7 H7 119.1 . . ?
C13 C8 C9 118.5(4) . . ?
C13 C8 N1 122.0(4) . . ?
C9 C8 N1 119.5(4) . . ?
C10 C9 C8 119.8(4) . . ?
C10 C9 H9 120.1 . . ?
C8 C9 H9 120.1 . . ?
C11 C10 C9 122.7(5) . . ?
C11 C10 H10 118.7 . . ?
C9 C10 H10 118.7 . . ?
C10 C11 C12 116.8(4) . . ?
C10 C11 C14 121.3(5) . . ?
C12 C11 C14 121.8(5) . . ?
C11 C12 C13 121.5(4) . . ?
C11 C12 H12 119.2 . . ?
C13 C12 H12 119.2 . . ?
C8 C13 C12 120.7(4) . . ?
C8 C13 H13 119.7 . . ?
C12 C13 H13 119.7 . . ?
C11 C14 H14A 109.5 . . ?
C11 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C11 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C16 C15 C29 120.5(3) . . ?
C16 C15 N1 119.9(4) . . ?
C29 C15 N1 119.7(4) . . ?
C15 C16 C17 121.9(4) . . ?
C15 C16 H16 119.0 . . ?
C17 C16 H16 119.0 . . ?
C18 C17 C16 118.6(4) . . ?
C18 C17 H17 120.7 . . ?
C16 C17 H17 120.7 . . ?
C17 C18 C28 119.5(3) . . ?
C17 C18 C19 132.3(3) . . ?
C28 C18 C19 108.2(3) . . ?
C20 C19 C30 117.4(3) . . ?
C20 C19 C18 136.3(3) . . ?
C30 C19 C18 106.3(3) . . ?
C19 C20 C21 119.9(3) . . ?
C19 C20 H20 120.1 . . ?
C21 C20 H20 120.1 . . ?
C22 C21 C20 123.0(3) . . ?
C22 C21 H21 118.5 . . ?
C20 C21 H21 118.5 . . ?
C21 C22 N4 121.4(3) . . ?
C21 C22 C23 119.1(3) . . ?
N4 C22 C23 119.3(3) . . ?
C30 C23 C24 116.4(3) . . ?
C30 C23 C22 115.1(3) . . ?
C24 C23 C22 128.5(3) . . ?
C25 C24 C23 119.8(3) . . ?
C25 C24 C31 117.4(4) . . ?
C23 C24 C31 122.6(3) . . ?
C24 C25 C26 122.0(3) . . ?
C24 C25 C32 119.4(3) . . ?
C26 C25 C32 118.6(3) . . ?
C27 C26 C25 118.8(3) . . ?
C27 C26 H26 120.6 . . ?
C25 C26 H26 120.6 . . ?
C26 C27 C30 119.6(3) . . ?
C26 C27 C28 134.6(3) . . ?
C30 C27 C28 105.8(3) . . ?
C29 C28 C18 121.4(3) . . ?
C29 C28 C27 130.5(4) . . ?
C18 C28 C27 108.1(3) . . ?
C28 C29 C15 118.0(4) . . ?
C28 C29 H29 121.0 . . ?
C15 C29 H29 121.0 . . ?
C23 C30 C19 125.1(3) . . ?
C23 C30 C27 123.3(3) . . ?
C19 C30 C27 111.6(3) . . ?
N2 C31 C24 173.9(5) . . ?
N3 C32 C25 176.9(5) . . ?
C38 C33 C34 118.7(4) . . ?
C38 C33 N4 122.0(3) . . ?
C34 C33 N4 119.3(4) . . ?
C35 C34 C33 120.2(4) . . ?
C35 C34 H34 119.9 . . ?
C33 C34 H34 119.9 . . ?
C34 C35 C36 122.4(4) . . ?
C34 C35 H35 118.8 . . ?
C36 C35 H35 118.8 . . ?
C37 C36 C35 117.0(4) . . ?
C37 C36 C39 121.8(5) . . ?
C35 C36 C39 121.2(5) . . ?
C36 C37 C38 121.6(4) . . ?
C36 C37 H37 119.2 . . ?
C38 C37 H37 119.2 . . ?
C33 C38 C37 120.1(4) . . ?
C33 C38 H38 119.9 . . ?
C37 C38 H38 119.9 . . ?
C36 C39 H39A 109.5 . . ?
C36 C39 H39B 109.5 . . ?
H39A C39 H39B 109.5 . . ?
C36 C39 H39C 109.5 . . ?
H39A C39 H39C 109.5 . . ?
H39B C39 H39C 109.5 . . ?
C45 C40 C41 118.1(4) . . ?
C45 C40 N4 120.0(3) . . ?
C41 C40 N4 121.9(3) . . ?
C42 C41 C40 120.5(4) . . ?
C42 C41 H41 119.7 . . ?
C40 C41 H41 119.7 . . ?
C43 C42 C41 121.3(4) . . ?
C43 C42 H42 119.4 . . ?
C41 C42 H42 119.4 . . ?
C42 C43 C44 118.0(4) . . ?
C42 C43 C46 120.8(4) . . ?
C44 C43 C46 121.2(5) . . ?
C43 C44 C45 121.9(4) . . ?
C43 C44 H44 119.1 . . ?
C45 C44 H44 119.1 . . ?
C44 C45 C40 120.2(4) . . ?
C44 C45 H45 119.9 . . ?
C40 C45 H45 119.9 . . ?
C43 C46 H46A 109.5 . . ?
C43 C46 H46B 109.5 . . ?
H46A C46 H46B 109.5 . . ?
C43 C46 H46C 109.5 . . ?
H46A C46 H46C 109.5 . . ?
H46B C46 H46C 109.5 . . ?
C8 N1 C5 122.5(3) . . ?
C8 N1 C15 119.7(3) . . ?
C5 N1 C15 116.8(3) . . ?
C40 N4 C22 119.0(3) . . ?
C40 N4 C33 118.0(3) . . ?
C22 N4 C33 116.6(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C7 C2 C3 C4 -0.3(6) . . . . ?
C1 C2 C3 C4 179.6(5) . . . . ?
C2 C3 C4 C5 -0.7(7) . . . . ?
C3 C4 C5 C6 0.7(6) . . . . ?
C3 C4 C5 N1 -177.4(4) . . . . ?
C4 C5 C6 C7 0.2(6) . . . . ?
N1 C5 C6 C7 178.3(4) . . . . ?
C3 C2 C7 C6 1.2(6) . . . . ?
C1 C2 C7 C6 -178.6(4) . . . . ?
C5 C6 C7 C2 -1.2(6) . . . . ?
C13 C8 C9 C10 -1.4(7) . . . . ?
N1 C8 C9 C10 177.4(4) . . . . ?
C8 C9 C10 C11 -0.8(8) . . . . ?
C9 C10 C11 C12 2.4(8) . . . . ?
C9 C10 C11 C14 -177.5(5) . . . . ?
C10 C11 C12 C13 -1.9(7) . . . . ?
C14 C11 C12 C13 178.0(5) . . . . ?
C9 C8 C13 C12 1.9(6) . . . . ?
N1 C8 C13 C12 -176.9(4) . . . . ?
C11 C12 C13 C8 -0.3(7) . . . . ?
C29 C15 C16 C17 2.9(6) . . . . ?
N1 C15 C16 C17 -175.3(4) . . . . ?
C15 C16 C17 C18 -0.6(6) . . . . ?
C16 C17 C18 C28 -1.2(6) . . . . ?
C16 C17 C18 C19 177.0(4) . . . . ?
C17 C18 C19 C20 2.6(8) . . . . ?
C28 C18 C19 C20 -179.0(4) . . . . ?
C17 C18 C19 C30 -177.2(4) . . . . ?
C28 C18 C19 C30 1.2(4) . . . . ?
C30 C19 C20 C21 4.5(5) . . . . ?
C18 C19 C20 C21 -175.3(4) . . . . ?
C19 C20 C21 C22 -1.6(6) . . . . ?
C20 C21 C22 N4 171.1(3) . . . . ?
C20 C21 C22 C23 -3.9(6) . . . . ?
C21 C22 C23 C30 6.0(5) . . . . ?
N4 C22 C23 C30 -169.1(3) . . . . ?
C21 C22 C23 C24 -172.7(4) . . . . ?
N4 C22 C23 C24 12.3(6) . . . . ?
C30 C23 C24 C25 1.6(5) . . . . ?
C22 C23 C24 C25 -179.8(4) . . . . ?
C30 C23 C24 C31 -173.2(3) . . . . ?
C22 C23 C24 C31 5.5(6) . . . . ?
C23 C24 C25 C26 2.2(6) . . . . ?
C31 C24 C25 C26 177.2(3) . . . . ?
C23 C24 C25 C32 -179.7(4) . . . . ?
C31 C24 C25 C32 -4.6(5) . . . . ?
C24 C25 C26 C27 -3.5(6) . . . . ?
C32 C25 C26 C27 178.3(4) . . . . ?
C25 C26 C27 C30 0.9(5) . . . . ?
C25 C26 C27 C28 -178.1(4) . . . . ?
C17 C18 C28 C29 0.8(6) . . . . ?
C19 C18 C28 C29 -177.9(3) . . . . ?
C17 C18 C28 C27 178.9(3) . . . . ?
C19 C18 C28 C27 0.2(4) . . . . ?
C26 C27 C28 C29 -4.6(7) . . . . ?
C30 C27 C28 C29 176.3(4) . . . . ?
C26 C27 C28 C18 177.5(4) . . . . ?
C30 C27 C28 C18 -1.6(4) . . . . ?
C18 C28 C29 C15 1.5(6) . . . . ?
C27 C28 C29 C15 -176.1(4) . . . . ?
C16 C15 C29 C28 -3.3(6) . . . . ?
N1 C15 C29 C28 174.9(4) . . . . ?
C24 C23 C30 C19 175.6(3) . . . . ?
C22 C23 C30 C19 -3.2(5) . . . . ?
C24 C23 C30 C27 -4.2(5) . . . . ?
C22 C23 C30 C27 176.9(3) . . . . ?
C20 C19 C30 C23 -2.0(5) . . . . ?
C18 C19 C30 C23 177.8(3) . . . . ?
C20 C19 C30 C27 177.9(3) . . . . ?
C18 C19 C30 C27 -2.3(4) . . . . ?
C26 C27 C30 C23 3.0(6) . . . . ?
C28 C27 C30 C23 -177.7(3) . . . . ?
C26 C27 C30 C19 -176.8(3) . . . . ?
C28 C27 C30 C19 2.5(4) . . . . ?
C38 C33 C34 C35 0.5(6) . . . . ?
N4 C33 C34 C35 -179.3(4) . . . . ?
C33 C34 C35 C36 -0.5(6) . . . . ?
C34 C35 C36 C37 0.0(6) . . . . ?
C34 C35 C36 C39 -178.9(4) . . . . ?
C35 C36 C37 C38 0.4(6) . . . . ?
C39 C36 C37 C38 179.4(4) . . . . ?
C34 C33 C38 C37 -0.1(6) . . . . ?
N4 C33 C38 C37 179.8(3) . . . . ?
C36 C37 C38 C33 -0.4(6) . . . . ?
C45 C40 C41 C42 1.6(6) . . . . ?
N4 C40 C41 C42 -178.7(4) . . . . ?
C40 C41 C42 C43 -0.7(6) . . . . ?
C41 C42 C43 C44 -0.4(7) . . . . ?
C41 C42 C43 C46 179.0(5) . . . . ?
C42 C43 C44 C45 0.5(8) . . . . ?
C46 C43 C44 C45 -178.9(5) . . . . ?
C43 C44 C45 C40 0.5(8) . . . . ?
C41 C40 C45 C44 -1.5(7) . . . . ?
N4 C40 C45 C44 178.8(4) . . . . ?
C13 C8 N1 C5 18.1(6) . . . . ?
C9 C8 N1 C5 -160.7(4) . . . . ?
C13 C8 N1 C15 -149.6(4) . . . . ?
C9 C8 N1 C15 31.6(6) . . . . ?
C4 C5 N1 C8 -135.6(4) . . . . ?
C6 C5 N1 C8 46.4(6) . . . . ?
C4 C5 N1 C15 32.4(6) . . . . ?
C6 C5 N1 C15 -145.6(4) . . . . ?
C16 C15 N1 C8 -113.6(5) . . . . ?
C29 C15 N1 C8 68.2(5) . . . . ?
C16 C15 N1 C5 78.1(5) . . . . ?
C29 C15 N1 C5 -100.2(5) . . . . ?
C45 C40 N4 C22 55.4(5) . . . . ?
C41 C40 N4 C22 -124.4(4) . . . . ?
C45 C40 N4 C33 -153.6(4) . . . . ?
C41 C40 N4 C33 26.7(5) . . . . ?
C21 C22 N4 C40 49.2(5) . . . . ?
C23 C22 N4 C40 -135.9(4) . . . . ?
C21 C22 N4 C33 -102.2(4) . . . . ?
C23 C22 N4 C33 72.7(4) . . . . ?
C38 C33 N4 C40 -126.4(4) . . . . ?
C34 C33 N4 C40 53.5(5) . . . . ?
C38 C33 N4 C22 25.4(5) . . . . ?
C34 C33 N4 C22 -154.8(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C4 H4 N2 0.93 2.63 3.346(6) 133.7 2_765
C4 H4 N2 0.93 2.63 3.346(6) 133.7 2_765
C4 H4 N2 0.93 2.63 3.346(6) 133.7 2_765
C4 H4 N2 0.93 2.63 3.346(6) 133.7 2_765
C4 H4 N2 0.93 2.63 3.346(6) 133.7 2_765

_refine_diff_density_max         0.292
_refine_diff_density_min         -0.281
_refine_diff_density_rms         0.064

