# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2020

####################################################################### 
# 
# 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. 
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#######################################################################

data_cd16585
_database_code_depnum_ccdc_archive 'CCDC 1509688'
_audit_update_record             
;
2016-10-13 deposited with the CCDC.	2020-07-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C36 H30 N2'
_chemical_formula_weight         490.62

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                   13.796(2)
_cell_length_b                   13.582(2)
_cell_length_c                   14.676(2)
_cell_angle_alpha                90
_cell_angle_beta                 110.931(4)
_cell_angle_gamma                90
_cell_volume                     2568.4(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1046
_cell_measurement_theta_min      5.648
_cell_measurement_theta_max      37.544

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.269
_exptl_crystal_F_000             1040
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.130
_exptl_absorpt_coefficient_mu    0.073
_shelx_estimated_absorpt_T_min   0.985
_shelx_estimated_absorpt_T_max   0.991
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5516
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13946
_diffrn_reflns_av_unetI/netI     0.0922
_diffrn_reflns_av_R_equivalents  0.0853
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.580
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 0.973
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 0.973
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 0.973
_reflns_number_total             4522
_reflns_number_gt                2475
_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 SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_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)+(0.0893P)²+0.1979P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4522
_refine_ls_number_parameters     373
_refine_ls_number_restraints     8
_refine_ls_R_factor_all          0.1439
_refine_ls_R_factor_gt           0.0789
_refine_ls_wR_factor_ref         0.2054
_refine_ls_wR_factor_gt          0.1731
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.042
_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 0.5476(2) 0.6281(2) 0.0983(2) 0.0450(8) Uani 1 1 d . . . . .
N2 N 0.3771(2) 0.6788(2) 0.1778(2) 0.0550(8) Uani 1 1 d . . . . .
C1 C 0.6446(2) 0.6031(2) 0.1031(2) 0.0408(9) Uani 1 1 d . . . . .
C2 C 0.6564(3) 0.5290(3) 0.0412(3) 0.0539(10) Uani 1 1 d . . . . .
H2 H 0.5984 0.4944 0.0018 0.065 Uiso 1 1 calc R U . . .
C3 C 0.7502(3) 0.5070(3) 0.0380(3) 0.0749(13) Uani 1 1 d . . . . .
H3 H 0.7564 0.4591 -0.0049 0.090 Uiso 1 1 calc R U . . .
C4 C 0.8385(3) 0.5565(3) 0.0994(4) 0.0798(14) Uani 1 1 d . . . . .
H4 H 0.9031 0.5415 0.0965 0.096 Uiso 1 1 calc R U . . .
C5 C 0.8309(3) 0.6259(3) 0.1628(3) 0.0620(11) Uani 1 1 d . . . . .
H5 H 0.8906 0.6576 0.2031 0.074 Uiso 1 1 calc R U . . .
C6 C 0.7341(2) 0.6511(2) 0.1689(2) 0.0426(9) Uani 1 1 d . . . . .
C7 C 0.7208(2) 0.7248(3) 0.2314(2) 0.0436(9) Uani 1 1 d . . . . .
C8 C 0.6218(3) 0.7512(3) 0.2247(2) 0.0480(9) Uani 1 1 d . . . . .
C9 C 0.5380(2) 0.6991(3) 0.1547(2) 0.0447(9) Uani 1 1 d . . . . .
C10 C 0.4298(2) 0.7306(3) 0.1402(2) 0.0426(9) Uani 1 1 d . . . . .
C11 C 0.3888(2) 0.8224(3) 0.0816(2) 0.0465(9) Uani 1 1 d . . . . .
C12 C 0.4611(3) 0.8754(3) 0.0366(3) 0.0651(12) Uani 1 1 d D . . . .
H12A H 0.5203 0.8364 0.0400 0.078 Uiso 0.5 1 d R U P A 1
H12B H 0.4783 0.9404 0.0621 0.078 Uiso 0.5 1 d R U P A 1
H12C H 0.5333 0.8604 0.0691 0.078 Uiso 0.5 1 d R U P B 2
H12D H 0.4463 0.9444 0.0251 0.078 Uiso 0.5 1 d R U P B 2
C14 C 0.3204(4) 0.7920(4) -0.0257(3) 0.0693(14) Uani 1 1 d D . . . .
H14A H 0.244(8) 0.797(8) -0.036(7) 0.083 Uiso 0.5 1 d . U P C 1
H14B H 0.338(7) 0.725(7) -0.043(6) 0.083 Uiso 0.5 1 d . U P D 1
H14C H 0.272(9) 0.839(7) -0.052(7) 0.083 Uiso 0.5 1 d . U P E 2
H14D H 0.283(7) 0.718(7) -0.018(6) 0.083 Uiso 0.5 1 d . U P F 2
C15 C 0.3392(2) 0.8871(2) 0.1404(2) 0.0438(9) Uani 1 1 d . . . . .
C16 C 0.4244(3) 0.9223(3) 0.2381(3) 0.0603(11) Uani 1 1 d D . . . .
H16A H 0.3874 0.9484 0.2776 0.072 Uiso 0.5 1 d R U P G 1
H16B H 0.4604 0.9754 0.2216 0.072 Uiso 0.5 1 d R U P G 1
H16C H 0.4104 0.8884 0.2896 0.072 Uiso 0.5 1 d R U P H 2
H16D H 0.4104 0.9904 0.2436 0.072 Uiso 0.5 1 d R U P H 2
C18 C 0.6018(3) 0.8292(3) 0.2889(3) 0.0773(14) Uani 1 1 d D . . . .
H18A H 0.6268 0.8893 0.2717 0.093 Uiso 0.5 1 d R U P I 1
H18B H 0.6478 0.8133 0.3537 0.093 Uiso 0.5 1 d R U P I 1
H18C H 0.6688 0.8523 0.3287 0.093 Uiso 0.5 1 d R U P J 2
H18D H 0.5748 0.7943 0.3317 0.093 Uiso 0.5 1 d R U P J 2
C19 C 0.2834(2) 0.7211(3) 0.1792(2) 0.0469(9) Uani 1 1 d . . . . .
C20 C 0.2174(3) 0.6605(3) 0.2052(3) 0.0635(11) Uani 1 1 d . . . . .
H20 H 0.2288 0.5929 0.2088 0.076 Uiso 1 1 calc R U . . .
C21 C 0.1352(3) 0.6981(4) 0.2257(3) 0.0686(12) Uani 1 1 d . . . . .
H21 H 0.0901 0.6563 0.2414 0.082 Uiso 1 1 calc R U . . .
C22 C 0.1206(3) 0.7982(4) 0.2229(3) 0.0646(12) Uani 1 1 d . . . . .
H22 H 0.0674 0.8248 0.2402 0.078 Uiso 1 1 calc R U . . .
C23 C 0.1843(3) 0.8593(3) 0.1947(2) 0.0558(10) Uani 1 1 d . . . . .
H23 H 0.1731 0.9269 0.1927 0.067 Uiso 1 1 calc R U . . .
C24 C 0.2650(3) 0.8221(3) 0.1691(2) 0.0442(9) Uani 1 1 d . . . . .
C25 C 0.2835(3) 0.9743(3) 0.0775(3) 0.0494(9) Uani 1 1 d . . . . .
C26 C 0.1825(3) 0.9638(3) 0.0095(3) 0.0624(11) Uani 1 1 d . . . . .
H26 H 0.1468 0.9053 0.0078 0.075 Uiso 1 1 calc R U . . .
C27 C 0.1346(4) 1.0379(4) -0.0549(3) 0.0856(15) Uani 1 1 d . . . . .
H27 H 0.0676 1.0288 -0.0993 0.103 Uiso 1 1 calc R U . . .
C28 C 0.1840(6) 1.1230(5) -0.0542(4) 0.1011(19) Uani 1 1 d . . . . .
H28 H 0.1512 1.1722 -0.0986 0.121 Uiso 1 1 calc R U . . .
C29 C 0.2815(6) 1.1380(4) 0.0109(5) 0.0953(17) Uani 1 1 d . . . . .
H29 H 0.3150 1.1974 0.0108 0.114 Uiso 1 1 calc R U . . .
C30 C 0.3319(4) 1.0645(3) 0.0781(3) 0.0715(12) Uani 1 1 d . . . . .
H30 H 0.3981 1.0759 0.1234 0.086 Uiso 1 1 calc R U . . .
C31 C 0.8142(2) 0.7734(3) 0.3024(2) 0.0458(9) Uani 1 1 d . . . . .
C32 C 0.8338(3) 0.8716(3) 0.2968(3) 0.0615(12) Uani 1 1 d . . . . .
H32 H 0.7877 0.9095 0.2475 0.074 Uiso 1 1 calc R U . . .
C33 C 0.9207(3) 0.9154(3) 0.3629(3) 0.0737(13) Uani 1 1 d . . . . .
H33 H 0.9331 0.9820 0.3577 0.088 Uiso 1 1 calc R U . . .
C34 C 0.9887(3) 0.8604(4) 0.4363(3) 0.0725(13) Uani 1 1 d . . . . .
H34 H 1.0472 0.8897 0.4811 0.087 Uiso 1 1 calc R U . . .
C35 C 0.9707(3) 0.7637(4) 0.4433(3) 0.0675(12) Uani 1 1 d . . . . .
H35 H 1.0169 0.7268 0.4936 0.081 Uiso 1 1 calc R U . . .
C36 C 0.8846(3) 0.7184(3) 0.3770(3) 0.0589(11) Uani 1 1 d . . . . .
H36 H 0.8738 0.6513 0.3821 0.071 Uiso 1 1 calc R U . . .
C13 C 0.3779(7) 0.8774(7) -0.0640(6) 0.059(3) Uani 0.5 1 d D . P K 1
H13A H 0.4016 0.8567 -0.1158 0.071 Uiso 0.5 1 calc R U P K 1
H13B H 0.3396 0.9388 -0.0802 0.071 Uiso 0.5 1 calc R U P K 1
C17 C 0.5033(5) 0.8547(6) 0.3004(5) 0.0490(19) Uani 0.5 1 d D . P L 1
H17A H 0.4679 0.7928 0.2989 0.059 Uiso 0.5 1 calc R U P L 1
H17B H 0.5218 0.8799 0.3663 0.059 Uiso 0.5 1 calc R U P L 1
C13' C 0.4061(9) 0.8100(12) -0.0570(7) 0.121(6) Uani 0.5 1 d D . P K 2
H13C H 0.3871 0.8464 -0.1177 0.145 Uiso 0.5 1 calc R U P K 2
H13D H 0.4446 0.7510 -0.0597 0.145 Uiso 0.5 1 calc R U P K 2
C17' C 0.5397(6) 0.9128(6) 0.2626(6) 0.060(2) Uani 0.5 1 d D . P L 2
H17C H 0.5522 0.9393 0.2064 0.071 Uiso 0.5 1 calc R U P L 2
H17D H 0.5705 0.9594 0.3151 0.071 Uiso 0.5 1 calc R U P L 2


_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 C9 1.308(4) . ?
N1 C1 1.358(4) . ?
N2 C10 1.272(4) . ?
N2 C19 1.420(4) . ?
C1 C2 1.404(5) . ?
C1 C6 1.424(4) . ?
C2 C3 1.344(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.401(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.356(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.411(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.414(5) . ?
C7 C8 1.381(5) . ?
C7 C31 1.491(4) . ?
C8 C9 1.430(4) . ?
C8 C18 1.507(5) . ?
C9 C10 1.493(5) . ?
C10 C11 1.506(5) . ?
C11 C15 1.551(5) . ?
C11 C12 1.555(5) . ?
C11 C14 1.575(5) . ?
C12 C13 1.513(8) . ?
C12 C13' 1.584(11) . ?
C12 H12A 0.9597 . ?
C12 H12B 0.9552 . ?
C12 H12C 0.9601 . ?
C12 H12D 0.9611 . ?
C14 C13' 1.434(12) . ?
C14 C13 1.616(11) . ?
C14 H14A 1.01(10) . ?
C14 H14B 1.00(9) . ?
C14 H14C 0.90(10) . ?
C14 H14D 1.16(9) . ?
C15 C24 1.521(5) . ?
C15 C25 1.530(5) . ?
C15 C16 1.569(4) . ?
C16 C17 1.467(7) . ?
C16 C17' 1.506(8) . ?
C16 H16A 0.9652 . ?
C16 H16B 0.9558 . ?
C16 H16C 0.9602 . ?
C16 H16D 0.9544 . ?
C18 C17' 1.392(8) . ?
C18 C17 1.470(8) . ?
C18 H18A 0.9540 . ?
C18 H18B 0.9605 . ?
C18 H18C 0.9526 . ?
C18 H18D 0.9623 . ?
C19 C20 1.378(5) . ?
C19 C24 1.394(5) . ?
C20 C21 1.372(6) . ?
C20 H20 0.9300 . ?
C21 C22 1.374(6) . ?
C21 H21 0.9300 . ?
C22 C23 1.375(5) . ?
C22 H22 0.9300 . ?
C23 C24 1.392(5) . ?
C23 H23 0.9300 . ?
C25 C30 1.393(5) . ?
C25 C26 1.402(5) . ?
C26 C27 1.376(5) . ?
C26 H26 0.9300 . ?
C27 C28 1.339(7) . ?
C27 H27 0.9300 . ?
C28 C29 1.359(7) . ?
C28 H28 0.9300 . ?
C29 C30 1.402(7) . ?
C29 H29 0.9300 . ?
C30 H30 0.9300 . ?
C31 C32 1.369(5) . ?
C31 C36 1.393(5) . ?
C32 C33 1.378(5) . ?
C32 H32 0.9300 . ?
C33 C34 1.369(6) . ?
C33 H33 0.9300 . ?
C34 C35 1.348(6) . ?
C34 H34 0.9300 . ?
C35 C36 1.382(5) . ?
C35 H35 0.9300 . ?
C36 H36 0.9300 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C13' H13C 0.9700 . ?
C13' H13D 0.9700 . ?
C17' H17C 0.9700 . ?
C17' H17D 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C9 N1 C1 118.1(3) . . ?
C10 N2 C19 116.6(3) . . ?
N1 C1 C2 119.0(3) . . ?
N1 C1 C6 121.4(3) . . ?
C2 C1 C6 119.6(3) . . ?
C3 C2 C1 121.1(3) . . ?
C3 C2 H2 119.4 . . ?
C1 C2 H2 119.4 . . ?
C2 C3 C4 119.8(4) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 H3 120.1 . . ?
C5 C4 C3 120.8(4) . . ?
C5 C4 H4 119.6 . . ?
C3 C4 H4 119.6 . . ?
C4 C5 C6 121.2(4) . . ?
C4 C5 H5 119.4 . . ?
C6 C5 H5 119.4 . . ?
C5 C6 C7 123.9(3) . . ?
C5 C6 C1 117.2(3) . . ?
C7 C6 C1 118.8(3) . . ?
C8 C7 C6 119.5(3) . . ?
C8 C7 C31 121.3(3) . . ?
C6 C7 C31 119.2(3) . . ?
C7 C8 C9 116.6(3) . . ?
C7 C8 C18 122.4(3) . . ?
C9 C8 C18 121.0(3) . . ?
N1 C9 C8 125.5(3) . . ?
N1 C9 C10 116.3(3) . . ?
C8 C9 C10 118.1(3) . . ?
N2 C10 C9 118.5(3) . . ?
N2 C10 C11 123.4(3) . . ?
C9 C10 C11 118.1(3) . . ?
C10 C11 C15 107.5(3) . . ?
C10 C11 C12 117.3(3) . . ?
C15 C11 C12 116.8(3) . . ?
C10 C11 C14 108.8(3) . . ?
C15 C11 C14 118.6(3) . . ?
C12 C11 C14 86.8(3) . . ?
C13 C12 C11 92.6(4) . . ?
C11 C12 C13' 85.8(5) . . ?
C13 C12 H12A 113.3 . . ?
C11 C12 H12A 112.6 . . ?
C13 C12 H12B 111.3 . . ?
C11 C12 H12B 111.6 . . ?
H12A C12 H12B 113.7 . . ?
C11 C12 H12C 113.5 . . ?
C13' C12 H12C 113.7 . . ?
C11 C12 H12D 113.4 . . ?
C13' C12 H12D 112.9 . . ?
H12C C12 H12D 114.3 . . ?
C13' C14 C11 90.4(5) . . ?
C11 C14 C13 88.1(4) . . ?
C11 C14 H14A 110(5) . . ?
C13 C14 H14A 121(7) . . ?
C11 C14 H14B 112(5) . . ?
C13 C14 H14B 112(6) . . ?
H14A C14 H14B 111(7) . . ?
C13' C14 H14C 108(7) . . ?
C11 C14 H14C 109(6) . . ?
C13' C14 H14D 129(5) . . ?
C11 C14 H14D 105(4) . . ?
H14C C14 H14D 111(7) . . ?
C24 C15 C25 112.0(3) . . ?
C24 C15 C11 107.4(3) . . ?
C25 C15 C11 109.3(3) . . ?
C24 C15 C16 106.3(3) . . ?
C25 C15 C16 111.5(3) . . ?
C11 C15 C16 110.2(3) . . ?
C17 C16 C15 121.7(4) . . ?
C17' C16 C15 125.0(4) . . ?
C17 C16 H16A 106.9 . . ?
C15 C16 H16A 106.0 . . ?
C17 C16 H16B 107.0 . . ?
C15 C16 H16B 106.5 . . ?
H16A C16 H16B 108.0 . . ?
C17' C16 H16C 105.3 . . ?
C15 C16 H16C 106.1 . . ?
C17' C16 H16D 106.9 . . ?
C15 C16 H16D 105.3 . . ?
H16C C16 H16D 107.2 . . ?
C17' C18 C8 129.2(5) . . ?
C17 C18 C8 128.4(4) . . ?
C17 C18 H18A 105.4 . . ?
C8 C18 H18A 105.8 . . ?
C17 C18 H18B 104.5 . . ?
C8 C18 H18B 104.9 . . ?
H18A C18 H18B 106.4 . . ?
C17' C18 H18C 105.6 . . ?
C8 C18 H18C 105.1 . . ?
C17' C18 H18D 103.9 . . ?
C8 C18 H18D 105.1 . . ?
H18C C18 H18D 106.2 . . ?
C20 C19 C24 120.2(4) . . ?
C20 C19 N2 117.2(3) . . ?
C24 C19 N2 121.9(3) . . ?
C21 C20 C19 121.3(4) . . ?
C21 C20 H20 119.4 . . ?
C19 C20 H20 119.4 . . ?
C20 C21 C22 119.1(4) . . ?
C20 C21 H21 120.5 . . ?
C22 C21 H21 120.5 . . ?
C21 C22 C23 120.2(4) . . ?
C21 C22 H22 119.9 . . ?
C23 C22 H22 119.9 . . ?
C22 C23 C24 121.4(4) . . ?
C22 C23 H23 119.3 . . ?
C24 C23 H23 119.3 . . ?
C23 C24 C19 117.5(3) . . ?
C23 C24 C15 123.2(3) . . ?
C19 C24 C15 119.1(3) . . ?
C30 C25 C26 116.5(4) . . ?
C30 C25 C15 122.7(3) . . ?
C26 C25 C15 120.6(3) . . ?
C27 C26 C25 121.7(4) . . ?
C27 C26 H26 119.2 . . ?
C25 C26 H26 119.2 . . ?
C28 C27 C26 120.5(5) . . ?
C28 C27 H27 119.7 . . ?
C26 C27 H27 119.7 . . ?
C27 C28 C29 120.5(5) . . ?
C27 C28 H28 119.7 . . ?
C29 C28 H28 119.7 . . ?
C28 C29 C30 120.4(5) . . ?
C28 C29 H29 119.8 . . ?
C30 C29 H29 119.8 . . ?
C25 C30 C29 120.3(5) . . ?
C25 C30 H30 119.8 . . ?
C29 C30 H30 119.8 . . ?
C32 C31 C36 118.1(3) . . ?
C32 C31 C7 122.0(3) . . ?
C36 C31 C7 119.8(3) . . ?
C31 C32 C33 121.3(3) . . ?
C31 C32 H32 119.4 . . ?
C33 C32 H32 119.4 . . ?
C34 C33 C32 119.8(4) . . ?
C34 C33 H33 120.1 . . ?
C32 C33 H33 120.1 . . ?
C35 C34 C33 119.9(4) . . ?
C35 C34 H34 120.1 . . ?
C33 C34 H34 120.1 . . ?
C34 C35 C36 121.0(4) . . ?
C34 C35 H35 119.5 . . ?
C36 C35 H35 119.5 . . ?
C35 C36 C31 119.8(4) . . ?
C35 C36 H36 120.1 . . ?
C31 C36 H36 120.1 . . ?
C12 C13 C14 86.7(5) . . ?
C12 C13 H13A 114.2 . . ?
C14 C13 H13A 114.2 . . ?
C12 C13 H13B 114.2 . . ?
C14 C13 H13B 114.2 . . ?
H13A C13 H13B 111.4 . . ?
C16 C17 C18 126.0(7) . . ?
C16 C17 H17A 105.8 . . ?
C18 C17 H17A 105.8 . . ?
C16 C17 H17B 105.8 . . ?
C18 C17 H17B 105.8 . . ?
H17A C17 H17B 106.2 . . ?
C14 C13' C12 90.7(6) . . ?
C14 C13' H13C 113.5 . . ?
C12 C13' H13C 113.5 . . ?
C14 C13' H13D 113.5 . . ?
C12 C13' H13D 113.5 . . ?
H13C C13' H13D 110.8 . . ?
C18 C17' C16 129.0(7) . . ?
C18 C17' H17C 105.0 . . ?
C16 C17' H17C 105.0 . . ?
C18 C17' H17D 105.0 . . ?
C16 C17' H17D 105.0 . . ?
H17C C17' H17D 105.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C9 N1 C1 C2 -178.2(3) . . . . ?
C9 N1 C1 C6 1.2(5) . . . . ?
N1 C1 C2 C3 174.8(4) . . . . ?
C6 C1 C2 C3 -4.6(6) . . . . ?
C1 C2 C3 C4 2.0(7) . . . . ?
C2 C3 C4 C5 0.5(7) . . . . ?
C3 C4 C5 C6 -0.3(7) . . . . ?
C4 C5 C6 C7 -178.1(4) . . . . ?
C4 C5 C6 C1 -2.3(6) . . . . ?
N1 C1 C6 C5 -174.7(3) . . . . ?
C2 C1 C6 C5 4.6(5) . . . . ?
N1 C1 C6 C7 1.3(5) . . . . ?
C2 C1 C6 C7 -179.3(3) . . . . ?
C5 C6 C7 C8 173.2(3) . . . . ?
C1 C6 C7 C8 -2.5(5) . . . . ?
C5 C6 C7 C31 -6.0(5) . . . . ?
C1 C6 C7 C31 178.3(3) . . . . ?
C6 C7 C8 C9 1.4(5) . . . . ?
C31 C7 C8 C9 -179.5(3) . . . . ?
C6 C7 C8 C18 -179.9(4) . . . . ?
C31 C7 C8 C18 -0.7(6) . . . . ?
C1 N1 C9 C8 -2.5(5) . . . . ?
C1 N1 C9 C10 174.3(3) . . . . ?
C7 C8 C9 N1 1.3(5) . . . . ?
C18 C8 C9 N1 -177.5(4) . . . . ?
C7 C8 C9 C10 -175.6(3) . . . . ?
C18 C8 C9 C10 5.7(5) . . . . ?
C19 N2 C10 C9 167.9(3) . . . . ?
C19 N2 C10 C11 -12.1(5) . . . . ?
N1 C9 C10 N2 79.6(4) . . . . ?
C8 C9 C10 N2 -103.3(4) . . . . ?
N1 C9 C10 C11 -100.4(4) . . . . ?
C8 C9 C10 C11 76.8(4) . . . . ?
N2 C10 C11 C15 48.4(4) . . . . ?
C9 C10 C11 C15 -131.6(3) . . . . ?
N2 C10 C11 C12 -177.5(3) . . . . ?
C9 C10 C11 C12 2.5(4) . . . . ?
N2 C10 C11 C14 -81.3(4) . . . . ?
C9 C10 C11 C14 98.7(4) . . . . ?
C10 C11 C12 C13 128.4(5) . . . . ?
C15 C11 C12 C13 -101.8(5) . . . . ?
C14 C11 C12 C13 18.8(5) . . . . ?
C10 C11 C12 C13' 91.9(6) . . . . ?
C15 C11 C12 C13' -138.2(6) . . . . ?
C14 C11 C12 C13' -17.6(6) . . . . ?
C10 C11 C14 C13' -98.3(7) . . . . ?
C15 C11 C14 C13' 138.4(7) . . . . ?
C12 C11 C14 C13' 19.5(7) . . . . ?
C10 C11 C14 C13 -135.4(5) . . . . ?
C15 C11 C14 C13 101.3(5) . . . . ?
C12 C11 C14 C13 -17.6(4) . . . . ?
C10 C11 C15 C24 -50.6(3) . . . . ?
C12 C11 C15 C24 175.0(3) . . . . ?
C14 C11 C15 C24 73.3(4) . . . . ?
C10 C11 C15 C25 -172.3(3) . . . . ?
C12 C11 C15 C25 53.3(4) . . . . ?
C14 C11 C15 C25 -48.4(5) . . . . ?
C10 C11 C15 C16 64.8(4) . . . . ?
C12 C11 C15 C16 -69.5(4) . . . . ?
C14 C11 C15 C16 -171.3(4) . . . . ?
C24 C15 C16 C17 71.4(6) . . . . ?
C25 C15 C16 C17 -166.3(5) . . . . ?
C11 C15 C16 C17 -44.7(6) . . . . ?
C24 C15 C16 C17' 127.8(6) . . . . ?
C25 C15 C16 C17' -109.9(6) . . . . ?
C11 C15 C16 C17' 11.6(7) . . . . ?
C7 C8 C18 C17' 126.4(6) . . . . ?
C9 C8 C18 C17' -54.9(8) . . . . ?
C7 C8 C18 C17 -170.1(5) . . . . ?
C9 C8 C18 C17 8.6(8) . . . . ?
C10 N2 C19 C20 169.9(3) . . . . ?
C10 N2 C19 C24 -19.4(5) . . . . ?
C24 C19 C20 C21 -2.9(5) . . . . ?
N2 C19 C20 C21 168.0(3) . . . . ?
C19 C20 C21 C22 -1.8(6) . . . . ?
C20 C21 C22 C23 3.5(6) . . . . ?
C21 C22 C23 C24 -0.5(5) . . . . ?
C22 C23 C24 C19 -4.1(5) . . . . ?
C22 C23 C24 C15 -178.2(3) . . . . ?
C20 C19 C24 C23 5.7(5) . . . . ?
N2 C19 C24 C23 -164.7(3) . . . . ?
C20 C19 C24 C15 -180.0(3) . . . . ?
N2 C19 C24 C15 9.6(5) . . . . ?
C25 C15 C24 C23 -39.2(4) . . . . ?
C11 C15 C24 C23 -159.2(3) . . . . ?
C16 C15 C24 C23 82.8(4) . . . . ?
C25 C15 C24 C19 146.8(3) . . . . ?
C11 C15 C24 C19 26.8(4) . . . . ?
C16 C15 C24 C19 -91.2(3) . . . . ?
C24 C15 C25 C30 149.9(3) . . . . ?
C11 C15 C25 C30 -91.3(4) . . . . ?
C16 C15 C25 C30 30.9(5) . . . . ?
C24 C15 C25 C26 -35.8(5) . . . . ?
C11 C15 C25 C26 83.1(4) . . . . ?
C16 C15 C25 C26 -154.8(3) . . . . ?
C30 C25 C26 C27 1.5(6) . . . . ?
C15 C25 C26 C27 -173.1(4) . . . . ?
C25 C26 C27 C28 -0.1(7) . . . . ?
C26 C27 C28 C29 -0.8(8) . . . . ?
C27 C28 C29 C30 0.1(9) . . . . ?
C26 C25 C30 C29 -2.2(6) . . . . ?
C15 C25 C30 C29 172.4(4) . . . . ?
C28 C29 C30 C25 1.4(7) . . . . ?
C8 C7 C31 C32 -63.7(5) . . . . ?
C6 C7 C31 C32 115.5(4) . . . . ?
C8 C7 C31 C36 116.5(4) . . . . ?
C6 C7 C31 C36 -64.3(5) . . . . ?
C36 C31 C32 C33 0.0(6) . . . . ?
C7 C31 C32 C33 -179.8(4) . . . . ?
C31 C32 C33 C34 -0.5(7) . . . . ?
C32 C33 C34 C35 0.3(7) . . . . ?
C33 C34 C35 C36 0.5(7) . . . . ?
C34 C35 C36 C31 -1.0(7) . . . . ?
C32 C31 C36 C35 0.8(6) . . . . ?
C7 C31 C36 C35 -179.4(4) . . . . ?
C11 C12 C13 C14 -18.3(4) . . . . ?
C13' C12 C13 C14 61.2(9) . . . . ?
C13' C14 C13 C12 -75.2(8) . . . . ?
C11 C14 C13 C12 18.1(4) . . . . ?
C17' C16 C17 C18 -25.5(6) . . . . ?
C15 C16 C17 C18 84.6(8) . . . . ?
C17' C18 C17 C16 26.9(6) . . . . ?
C8 C18 C17 C16 -85.2(9) . . . . ?
C11 C14 C13' C12 -19.1(6) . . . . ?
C13 C14 C13' C12 67.2(9) . . . . ?
C13 C12 C13' C14 -80.5(10) . . . . ?
C11 C12 C13' C14 19.4(7) . . . . ?
C17 C18 C17' C16 -27.3(6) . . . . ?
C8 C18 C17' C16 83.0(10) . . . . ?
C17 C16 C17' C18 28.2(7) . . . . ?
C15 C16 C17' C18 -74.5(10) . . . . ?

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
C2 H2 N1 0.93 2.62 3.542(4) 170.9 3_665
C2 H2 N1 0.93 2.62 3.542(4) 170.9 3_665

_refine_diff_density_max         0.312
_refine_diff_density_min         -0.206
_refine_diff_density_rms         0.052

_shelxl_version_number           2013-4



