# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2022

####################################################################### 
# 
# 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_hek3
_database_code_depnum_ccdc_archive 'CCDC 2205008'
loop_
_audit_author_name
_audit_author_address
'Frank Rominger'
;Heidelberg University
Germany
;
_audit_update_record             
;
2022-09-02 deposited with the CCDC.	2022-10-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            '**2a** in manuscript'
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C56 H46 N4'
_chemical_formula_weight         774.97

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

_space_group_crystal_system      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                   9.3971(4)
_cell_length_b                   11.2369(4)
_cell_length_c                   19.4152(10)
_cell_angle_alpha                90
_cell_angle_beta                 91.402(4)
_cell_angle_gamma                90
_cell_volume                     2049.52(16)
_cell_formula_units_Z            2
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    6433
_cell_measurement_theta_min      4.55
_cell_measurement_theta_max      66.99

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.256
_exptl_crystal_F_000             820
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.190
_exptl_crystal_size_mid          0.030
_exptl_crystal_size_min          0.027
_exptl_absorpt_coefficient_mu    0.562
_shelx_estimated_absorpt_T_min   0.901
_shelx_estimated_absorpt_T_max   0.985
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.739
_exptl_absorpt_correction_T_max  1.290
_exptl_absorpt_process_details   'STOE X-AREA LANA'
_exptl_absorpt_special_details   'X-Area LANA 1.70.0.0 (STOE, 2017)'
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Genix3D Cu HF'
_diffrn_measurement_device_type  'STOE Stadivari'
_diffrn_measurement_method       'rotation method, ω scans'
_diffrn_detector_area_resol_mean 5.81
_diffrn_reflns_number            12146
_diffrn_reflns_av_unetI/netI     0.0605
_diffrn_reflns_av_R_equivalents  0.0608
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         4.547
_diffrn_reflns_theta_max         67.133
_diffrn_reflns_theta_full        67.133
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measured_fraction_theta_full 0.973
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_Laue_measured_fraction_full 0.973
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_point_group_measured_fraction_full 0.973
_reflns_number_total             3572
_reflns_number_gt                2135
_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       'X-Area Pilatus3_SV 1.31.144.0 (STOE, 2018)'
_computing_cell_refinement       'X-Area Recipe 1.33.0.0 (STOE, 2015)'
_computing_data_reduction        'X-Area Integrate 1.73.0.0 (STOE, 2018)'
_computing_structure_solution    'SHELXT-2014 (Sheldrick 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0600P)²+0.3656P] 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         3572
_refine_ls_number_parameters     302
_refine_ls_number_restraints     314
_refine_ls_R_factor_all          0.1126
_refine_ls_R_factor_gt           0.0549
_refine_ls_wR_factor_ref         0.1371
_refine_ls_wR_factor_gt          0.1143
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      0.996
_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
C11 C 0.5339(2) 0.5983(2) 0.54451(13) 0.0360(6) Uani 1 1 d . . . . .
H11 H 0.557193 0.662594 0.574529 0.043 Uiso 1 1 calc R U . . .
C12 C 0.4050(2) 0.5950(2) 0.50720(12) 0.0337(6) Uani 1 1 d . . . . .
C13 C 0.2849(3) 0.6741(2) 0.50007(13) 0.0344(6) Uani 1 1 d . . . . .
C14 C 0.2530(3) 0.7885(2) 0.52614(13) 0.0361(6) Uani 1 1 d . . . . .
N15 N 0.1331(2) 0.84443(19) 0.50998(11) 0.0405(6) Uani 1 1 d . . . . .
C16 C 0.0312(3) 0.7868(2) 0.46950(13) 0.0375(6) Uani 1 1 d . . . . .
C17 C -0.0963(3) 0.8495(3) 0.45517(14) 0.0427(7) Uani 1 1 d . . . . .
H17 H -0.104953 0.930123 0.469102 0.051 Uiso 1 1 calc R U . . .
C18 C -0.2072(3) 0.7947(3) 0.42141(14) 0.0454(7) Uani 1 1 d . . . . .
H18 H -0.292354 0.837642 0.411553 0.054 Uiso 1 1 calc R U . . .
C19 C -0.1960(3) 0.6756(3) 0.40122(13) 0.0435(7) Uani 1 1 d . . . . .
H19 H -0.276066 0.636816 0.380478 0.052 Uiso 1 1 calc R U . . .
C20 C -0.0715(3) 0.6142(3) 0.41096(13) 0.0411(7) Uani 1 1 d . . . . .
H20 H -0.064725 0.534084 0.395818 0.049 Uiso 1 1 calc R U . . .
C21 C 0.0472(3) 0.6698(2) 0.44352(12) 0.0357(6) Uani 1 1 d . . . . .
C22 C 0.1840(2) 0.6186(2) 0.45636(12) 0.0332(6) Uani 1 1 d . . . . .
N23 N 0.2385(2) 0.51161(19) 0.43387(10) 0.0355(5) Uani 1 1 d . . . . .
C24 C 0.3742(2) 0.4956(2) 0.46415(12) 0.0344(6) Uani 1 1 d . . . . .
C31 C 0.3525(3) 0.8566(2) 0.57228(13) 0.0366(6) Uani 1 1 d D . . . .
C32 C 0.3053(3) 0.9013(2) 0.63381(14) 0.0431(7) Uani 1 1 d D . . . .
H32 H 0.211787 0.883214 0.648085 0.052 Uiso 1 1 calc R U . . .
C33 C 0.3927(3) 0.9721(3) 0.67506(14) 0.0479(7) Uani 1 1 d D . . . .
H33 H 0.358235 0.999643 0.717801 0.058 Uiso 1 1 calc R U . . .
C34 C 0.5284(3) 1.0043(2) 0.65628(13) 0.0404(7) Uani 1 1 d D . . . .
C35 C 0.5762(3) 0.9574(3) 0.59489(15) 0.0466(7) Uani 1 1 d D . . . .
H35 H 0.669748 0.975531 0.580623 0.056 Uiso 1 1 calc R U . . .
C36 C 0.4896(3) 0.8839(3) 0.55368(15) 0.0448(7) Uani 1 1 d D . . . .
H36 H 0.525578 0.852294 0.512200 0.054 Uiso 1 1 calc R U . . .
C38 C 0.6156(3) 1.0900(3) 0.70114(15) 0.0527(8) Uani 1 1 d D . . . .
C381 C 0.7584(4) 1.1228(5) 0.6679(2) 0.0764(17) Uani 0.833(8) 1 d D . P A 1
H38A H 0.810012 1.179817 0.697346 0.115 Uiso 0.833(8) 1 calc R U P A 1
H38B H 0.739598 1.158425 0.622484 0.115 Uiso 0.833(8) 1 calc R U P A 1
H38C H 0.816046 1.050766 0.662675 0.115 Uiso 0.833(8) 1 calc R U P A 1
C382 C 0.6490(7) 1.0349(5) 0.7704(2) 0.087(2) Uani 0.833(8) 1 d D . P A 1
H38D H 0.705014 1.090907 0.798656 0.131 Uiso 0.833(8) 1 calc R U P A 1
H38E H 0.703632 0.961571 0.764138 0.131 Uiso 0.833(8) 1 calc R U P A 1
H38F H 0.560029 1.016382 0.793418 0.131 Uiso 0.833(8) 1 calc R U P A 1
C383 C 0.5355(6) 1.2073(5) 0.7078(5) 0.114(3) Uani 0.833(8) 1 d D . P A 1
H38G H 0.588848 1.260517 0.739003 0.170 Uiso 0.833(8) 1 calc R U P A 1
H38H H 0.441136 1.192106 0.726381 0.170 Uiso 0.833(8) 1 calc R U P A 1
H38I H 0.524923 1.244735 0.662391 0.170 Uiso 0.833(8) 1 calc R U P A 1
C384 C 0.552(2) 1.097(2) 0.7742(7) 0.067(7) Uani 0.167(8) 1 d D . P A 2
H38J H 0.554533 1.018051 0.795527 0.100 Uiso 0.167(8) 1 calc R U P A 2
H38K H 0.607870 1.152848 0.802610 0.100 Uiso 0.167(8) 1 calc R U P A 2
H38L H 0.453125 1.124751 0.770389 0.100 Uiso 0.167(8) 1 calc R U P A 2
C385 C 0.606(4) 1.2161(14) 0.6729(11) 0.080(9) Uani 0.167(8) 1 d D . P A 2
H38M H 0.663228 1.269503 0.702550 0.120 Uiso 0.167(8) 1 calc R U P A 2
H38N H 0.643196 1.217799 0.626124 0.120 Uiso 0.167(8) 1 calc R U P A 2
H38O H 0.506946 1.242383 0.671897 0.120 Uiso 0.167(8) 1 calc R U P A 2
C386 C 0.765(3) 1.028(3) 0.7211(19) 0.127(13) Uani 0.167(8) 1 d . . P A 2
H38P H 0.748317 0.947446 0.738169 0.190 Uiso 0.167(8) 1 calc R U P A 2
H38Q H 0.824290 1.024325 0.680222 0.190 Uiso 0.167(8) 1 calc R U P A 2
H38R H 0.814363 1.074970 0.756993 0.190 Uiso 0.167(8) 1 calc R U P A 2
C41 C 0.1810(2) 0.4351(2) 0.38126(13) 0.0352(6) Uani 1 1 d . . . . .
C42 C 0.1557(3) 0.3176(3) 0.39666(15) 0.0468(7) Uani 1 1 d . . . . .
H42 H 0.174205 0.288635 0.441959 0.056 Uiso 1 1 calc R U . . .
C43 C 0.1031(3) 0.2418(3) 0.34595(18) 0.0616(9) Uani 1 1 d . . . . .
H43 H 0.084312 0.160916 0.356664 0.074 Uiso 1 1 calc R U . . .
C44 C 0.0780(3) 0.2831(4) 0.28014(18) 0.0642(9) Uani 1 1 d . . . . .
H44 H 0.043889 0.230584 0.245145 0.077 Uiso 1 1 calc R U . . .
C45 C 0.1025(3) 0.4009(3) 0.26514(15) 0.0594(9) Uani 1 1 d . . . . .
H45 H 0.083154 0.429883 0.219908 0.071 Uiso 1 1 calc R U . . .
C46 C 0.1552(3) 0.4777(3) 0.31550(13) 0.0457(7) Uani 1 1 d . . . . .
H46 H 0.173283 0.558708 0.304851 0.055 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
C11 C24 1.376(3) 3_666 ?
C11 C12 1.397(3) . ?
C11 H11 0.9500 . ?
C12 C24 1.421(3) . ?
C12 C13 1.440(3) . ?
C13 C22 1.404(3) . ?
C13 C14 1.417(4) . ?
C14 N15 1.321(3) . ?
C14 C31 1.490(3) . ?
N15 C16 1.385(3) . ?
C16 C17 1.412(3) . ?
C16 C21 1.417(4) . ?
C17 C18 1.364(4) . ?
C17 H17 0.9500 . ?
C18 C19 1.400(4) . ?
C18 H18 0.9500 . ?
C19 C20 1.367(4) . ?
C19 H19 0.9500 . ?
C20 C21 1.414(3) . ?
C20 H20 0.9500 . ?
C21 C22 1.424(3) . ?
C22 N23 1.381(3) . ?
N23 C24 1.403(3) . ?
N23 C41 1.431(3) . ?
C31 C32 1.379(3) . ?
C31 C36 1.381(4) . ?
C32 C33 1.385(4) . ?
C32 H32 0.9500 . ?
C33 C34 1.383(4) . ?
C33 H33 0.9500 . ?
C34 C35 1.388(4) . ?
C34 C38 1.524(4) . ?
C35 C36 1.397(4) . ?
C35 H35 0.9500 . ?
C36 H36 0.9500 . ?
C38 C382 1.506(5) . ?
C38 C385 1.522(13) . ?
C38 C383 1.526(5) . ?
C38 C381 1.548(5) . ?
C38 C384 1.555(12) . ?
C38 C386 1.61(3) . ?
C381 H38A 0.9800 . ?
C381 H38B 0.9800 . ?
C381 H38C 0.9800 . ?
C382 H38D 0.9800 . ?
C382 H38E 0.9800 . ?
C382 H38F 0.9800 . ?
C383 H38G 0.9800 . ?
C383 H38H 0.9800 . ?
C383 H38I 0.9800 . ?
C384 H38J 0.9800 . ?
C384 H38K 0.9800 . ?
C384 H38L 0.9800 . ?
C385 H38M 0.9800 . ?
C385 H38N 0.9800 . ?
C385 H38O 0.9800 . ?
C386 H38P 0.9800 . ?
C386 H38Q 0.9800 . ?
C386 H38R 0.9800 . ?
C41 C42 1.375(4) . ?
C41 C46 1.379(4) . ?
C42 C43 1.384(4) . ?
C42 H42 0.9500 . ?
C43 C44 1.374(5) . ?
C43 H43 0.9500 . ?
C44 C45 1.376(5) . ?
C44 H44 0.9500 . ?
C45 C46 1.386(4) . ?
C45 H45 0.9500 . ?
C46 H46 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
C24 C11 C12 117.0(2) 3_666 . ?
C24 C11 H11 121.5 3_666 . ?
C12 C11 H11 121.5 . . ?
C11 C12 C24 119.2(2) . . ?
C11 C12 C13 134.5(2) . . ?
C24 C12 C13 106.3(2) . . ?
C22 C13 C14 118.2(2) . . ?
C22 C13 C12 107.5(2) . . ?
C14 C13 C12 134.3(2) . . ?
N15 C14 C13 122.3(2) . . ?
N15 C14 C31 114.7(2) . . ?
C13 C14 C31 123.0(2) . . ?
C14 N15 C16 119.1(2) . . ?
N15 C16 C17 116.8(2) . . ?
N15 C16 C21 123.9(2) . . ?
C17 C16 C21 119.3(2) . . ?
C18 C17 C16 120.3(3) . . ?
C18 C17 H17 119.9 . . ?
C16 C17 H17 119.9 . . ?
C17 C18 C19 120.3(2) . . ?
C17 C18 H18 119.8 . . ?
C19 C18 H18 119.8 . . ?
C20 C19 C18 120.9(3) . . ?
C20 C19 H19 119.6 . . ?
C18 C19 H19 119.6 . . ?
C19 C20 C21 120.2(3) . . ?
C19 C20 H20 119.9 . . ?
C21 C20 H20 119.9 . . ?
C20 C21 C16 118.6(2) . . ?
C20 C21 C22 126.8(2) . . ?
C16 C21 C22 114.6(2) . . ?
N23 C22 C13 109.1(2) . . ?
N23 C22 C21 129.5(2) . . ?
C13 C22 C21 121.3(2) . . ?
C22 N23 C24 108.62(19) . . ?
C22 N23 C41 127.7(2) . . ?
C24 N23 C41 123.1(2) . . ?
C11 C24 N23 127.8(2) 3_666 . ?
C11 C24 C12 123.8(2) 3_666 . ?
N23 C24 C12 108.4(2) . . ?
C32 C31 C36 117.8(2) . . ?
C32 C31 C14 119.8(2) . . ?
C36 C31 C14 122.2(2) . . ?
C31 C32 C33 120.8(3) . . ?
C31 C32 H32 119.6 . . ?
C33 C32 H32 119.6 . . ?
C34 C33 C32 122.4(3) . . ?
C34 C33 H33 118.8 . . ?
C32 C33 H33 118.8 . . ?
C33 C34 C35 116.5(2) . . ?
C33 C34 C38 120.1(3) . . ?
C35 C34 C38 123.4(2) . . ?
C34 C35 C36 121.3(3) . . ?
C34 C35 H35 119.3 . . ?
C36 C35 H35 119.3 . . ?
C31 C36 C35 121.1(3) . . ?
C31 C36 H36 119.5 . . ?
C35 C36 H36 119.5 . . ?
C382 C38 C34 110.4(3) . . ?
C385 C38 C34 111.0(10) . . ?
C382 C38 C383 111.8(4) . . ?
C34 C38 C383 109.6(3) . . ?
C382 C38 C381 107.9(3) . . ?
C34 C38 C381 111.8(3) . . ?
C383 C38 C381 105.4(4) . . ?
C385 C38 C384 105.1(12) . . ?
C34 C38 C384 109.9(7) . . ?
C385 C38 C386 122.1(19) . . ?
C34 C38 C386 108.7(11) . . ?
C384 C38 C386 99.0(16) . . ?
C38 C381 H38A 109.5 . . ?
C38 C381 H38B 109.5 . . ?
H38A C381 H38B 109.5 . . ?
C38 C381 H38C 109.5 . . ?
H38A C381 H38C 109.5 . . ?
H38B C381 H38C 109.5 . . ?
C38 C382 H38D 109.5 . . ?
C38 C382 H38E 109.5 . . ?
H38D C382 H38E 109.5 . . ?
C38 C382 H38F 109.5 . . ?
H38D C382 H38F 109.5 . . ?
H38E C382 H38F 109.5 . . ?
C38 C383 H38G 109.5 . . ?
C38 C383 H38H 109.5 . . ?
H38G C383 H38H 109.5 . . ?
C38 C383 H38I 109.5 . . ?
H38G C383 H38I 109.5 . . ?
H38H C383 H38I 109.5 . . ?
C38 C384 H38J 109.5 . . ?
C38 C384 H38K 109.5 . . ?
H38J C384 H38K 109.5 . . ?
C38 C384 H38L 109.5 . . ?
H38J C384 H38L 109.5 . . ?
H38K C384 H38L 109.5 . . ?
C38 C385 H38M 109.5 . . ?
C38 C385 H38N 109.5 . . ?
H38M C385 H38N 109.5 . . ?
C38 C385 H38O 109.5 . . ?
H38M C385 H38O 109.5 . . ?
H38N C385 H38O 109.5 . . ?
C38 C386 H38P 109.5 . . ?
C38 C386 H38Q 109.5 . . ?
H38P C386 H38Q 109.5 . . ?
C38 C386 H38R 109.5 . . ?
H38P C386 H38R 109.5 . . ?
H38Q C386 H38R 109.5 . . ?
C42 C41 C46 120.5(3) . . ?
C42 C41 N23 119.1(2) . . ?
C46 C41 N23 120.5(2) . . ?
C41 C42 C43 119.8(3) . . ?
C41 C42 H42 120.1 . . ?
C43 C42 H42 120.1 . . ?
C44 C43 C42 120.2(3) . . ?
C44 C43 H43 119.9 . . ?
C42 C43 H43 119.9 . . ?
C43 C44 C45 119.7(3) . . ?
C43 C44 H44 120.1 . . ?
C45 C44 H44 120.1 . . ?
C44 C45 C46 120.5(3) . . ?
C44 C45 H45 119.7 . . ?
C46 C45 H45 119.7 . . ?
C41 C46 C45 119.3(3) . . ?
C41 C46 H46 120.4 . . ?
C45 C46 H46 120.4 . . ?

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
C24 C11 C12 C24 1.3(4) 3_666 . . . ?
C24 C11 C12 C13 -178.0(3) 3_666 . . . ?
C11 C12 C13 C22 -177.9(3) . . . . ?
C24 C12 C13 C22 2.8(3) . . . . ?
C11 C12 C13 C14 2.9(5) . . . . ?
C24 C12 C13 C14 -176.4(3) . . . . ?
C22 C13 C14 N15 -0.9(4) . . . . ?
C12 C13 C14 N15 178.3(3) . . . . ?
C22 C13 C14 C31 -179.3(2) . . . . ?
C12 C13 C14 C31 -0.2(5) . . . . ?
C13 C14 N15 C16 3.9(4) . . . . ?
C31 C14 N15 C16 -177.5(2) . . . . ?
C14 N15 C16 C17 178.5(2) . . . . ?
C14 N15 C16 C21 -0.3(4) . . . . ?
N15 C16 C17 C18 -173.6(3) . . . . ?
C21 C16 C17 C18 5.2(4) . . . . ?
C16 C17 C18 C19 0.6(4) . . . . ?
C17 C18 C19 C20 -4.2(4) . . . . ?
C18 C19 C20 C21 1.8(4) . . . . ?
C19 C20 C21 C16 4.0(4) . . . . ?
C19 C20 C21 C22 -179.0(3) . . . . ?
N15 C16 C21 C20 171.3(2) . . . . ?
C17 C16 C21 C20 -7.4(4) . . . . ?
N15 C16 C21 C22 -6.1(4) . . . . ?
C17 C16 C21 C22 175.2(2) . . . . ?
C14 C13 C22 N23 176.8(2) . . . . ?
C12 C13 C22 N23 -2.6(3) . . . . ?
C14 C13 C22 C21 -6.0(4) . . . . ?
C12 C13 C22 C21 174.6(2) . . . . ?
C20 C21 C22 N23 8.5(4) . . . . ?
C16 C21 C22 N23 -174.4(2) . . . . ?
C20 C21 C22 C13 -168.1(3) . . . . ?
C16 C21 C22 C13 9.1(3) . . . . ?
C13 C22 N23 C24 1.3(3) . . . . ?
C21 C22 N23 C24 -175.6(2) . . . . ?
C13 C22 N23 C41 -170.1(2) . . . . ?
C21 C22 N23 C41 13.0(4) . . . . ?
C22 N23 C24 C11 -179.6(2) . . . 3_666 ?
C41 N23 C24 C11 -7.7(4) . . . 3_666 ?
C22 N23 C24 C12 0.5(3) . . . . ?
C41 N23 C24 C12 172.4(2) . . . . ?
C11 C12 C24 C11 -1.4(4) . . . 3_666 ?
C13 C12 C24 C11 178.1(2) . . . 3_666 ?
C11 C12 C24 N23 178.5(2) . . . . ?
C13 C12 C24 N23 -2.0(3) . . . . ?
N15 C14 C31 C32 53.8(3) . . . . ?
C13 C14 C31 C32 -127.6(3) . . . . ?
N15 C14 C31 C36 -121.8(3) . . . . ?
C13 C14 C31 C36 56.8(4) . . . . ?
C36 C31 C32 C33 0.6(4) . . . . ?
C14 C31 C32 C33 -175.2(3) . . . . ?
C31 C32 C33 C34 1.8(4) . . . . ?
C32 C33 C34 C35 -2.9(4) . . . . ?
C32 C33 C34 C38 175.4(3) . . . . ?
C33 C34 C35 C36 1.6(4) . . . . ?
C38 C34 C35 C36 -176.7(3) . . . . ?
C32 C31 C36 C35 -1.9(4) . . . . ?
C14 C31 C36 C35 173.8(3) . . . . ?
C34 C35 C36 C31 0.7(4) . . . . ?
C33 C34 C38 C382 64.9(4) . . . . ?
C35 C34 C38 C382 -116.9(4) . . . . ?
C33 C34 C38 C385 -98.2(13) . . . . ?
C35 C34 C38 C385 80.0(14) . . . . ?
C33 C34 C38 C383 -58.6(5) . . . . ?
C35 C34 C38 C383 119.6(5) . . . . ?
C33 C34 C38 C381 -175.0(3) . . . . ?
C35 C34 C38 C381 3.2(4) . . . . ?
C33 C34 C38 C384 17.6(12) . . . . ?
C35 C34 C38 C384 -164.1(12) . . . . ?
C33 C34 C38 C386 125.0(17) . . . . ?
C35 C34 C38 C386 -56.8(17) . . . . ?
C22 N23 C41 C42 -125.5(3) . . . . ?
C24 N23 C41 C42 64.2(3) . . . . ?
C22 N23 C41 C46 56.3(4) . . . . ?
C24 N23 C41 C46 -113.9(3) . . . . ?
C46 C41 C42 C43 -0.4(4) . . . . ?
N23 C41 C42 C43 -178.5(2) . . . . ?
C41 C42 C43 C44 0.9(4) . . . . ?
C42 C43 C44 C45 -1.4(5) . . . . ?
C43 C44 C45 C46 1.4(5) . . . . ?
C42 C41 C46 C45 0.4(4) . . . . ?
N23 C41 C46 C45 178.5(2) . . . . ?
C44 C45 C46 C41 -0.9(4) . . . . ?

_refine_diff_density_max         0.249
_refine_diff_density_min         -0.185
_refine_diff_density_rms         0.041

####################################################################### 
# 
# 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_hek4
_database_code_depnum_ccdc_archive 'CCDC 2205009'
loop_
_audit_author_name
_audit_author_address
'Frank Rominger'
;Heidelberg University
Germany
;
_audit_update_record             
;
2022-09-02 deposited with the CCDC.	2022-10-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            '**2c** in manuscript'
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C50 H34 N4 O2'
_chemical_formula_weight         722.81

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

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

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

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

_cell_length_a                   18.2588(10)
_cell_length_b                   7.7639(3)
_cell_length_c                   27.0581(19)
_cell_angle_alpha                90
_cell_angle_beta                 108.351(4)
_cell_angle_gamma                90
_cell_volume                     3640.7(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    8215
_cell_measurement_theta_min      3.44
_cell_measurement_theta_max      65.56

_exptl_crystal_description       plate
_exptl_crystal_colour            'pale Yellow'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.319
_exptl_crystal_F_000             1512
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.127
_exptl_crystal_size_min          0.010
_exptl_absorpt_coefficient_mu    0.639
_shelx_estimated_absorpt_T_min   0.700
_shelx_estimated_absorpt_T_max   0.994
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.728
_exptl_absorpt_correction_T_max  1.493
_exptl_absorpt_process_details   'STOE X-AREA LANA'
_exptl_absorpt_special_details   'X-Area LANA 1.70.0.0 (STOE, 2017)'
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Genix3D Cu HF'
_diffrn_measurement_device_type  'STOE Stadivari'
_diffrn_measurement_method       'rotation method, ω scans'
_diffrn_detector_area_resol_mean 5.81
_diffrn_reflns_number            10345
_diffrn_reflns_av_unetI/netI     0.0369
_diffrn_reflns_av_R_equivalents  0.0500
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         5.104
_diffrn_reflns_theta_max         67.238
_diffrn_reflns_theta_full        67.238
_diffrn_measured_fraction_theta_max 0.961
_diffrn_measured_fraction_theta_full 0.961
_diffrn_reflns_Laue_measured_fraction_max 0.961
_diffrn_reflns_Laue_measured_fraction_full 0.961
_diffrn_reflns_point_group_measured_fraction_max 0.961
_diffrn_reflns_point_group_measured_fraction_full 0.961
_reflns_number_total             3138
_reflns_number_gt                1891
_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       'X-Area Pilatus3_SV 1.31.144.0 (STOE, 2018)'
_computing_cell_refinement       'X-Area Recipe 1.33.0.0 (STOE, 2015)'
_computing_data_reduction        'X-Area Integrate 1.73.0.0 (STOE, 2018)'
_computing_structure_solution    'SHELXT-2014 (Sheldrick 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0640P)²+2.4689P] 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         3138
_refine_ls_number_parameters     254
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1022
_refine_ls_R_factor_gt           0.0536
_refine_ls_wR_factor_ref         0.1503
_refine_ls_wR_factor_gt          0.1206
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_restrained_S_all      1.016
_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
O38 O 0.54555(11) 0.1046(2) 0.59345(7) 0.0686(6) Uani 1 1 d . . . . .
N15 N 0.30247(13) 0.2984(3) 0.37404(10) 0.0656(6) Uani 1 1 d . . . . .
N23 N 0.16917(11) 0.7068(3) 0.39662(9) 0.0584(6) Uani 1 1 d . . . . .
C11 C 0.31185(14) 0.6293(4) 0.52140(11) 0.0579(7) Uani 1 1 d . . . . .
H11 H 0.353149 0.551399 0.535903 0.069 Uiso 1 1 calc R U . . .
C12 C 0.26577(14) 0.6187(3) 0.46934(11) 0.0560(7) Uani 1 1 d . . . . .
C13 C 0.26450(14) 0.5088(3) 0.42578(11) 0.0567(7) Uani 1 1 d . . . . .
C14 C 0.31149(15) 0.3711(4) 0.42003(12) 0.0598(7) Uani 1 1 d . . . . .
C16 C 0.24426(15) 0.3569(4) 0.33139(12) 0.0631(7) Uani 1 1 d . . . . .
C17 C 0.23629(17) 0.2741(4) 0.28337(12) 0.0703(8) Uani 1 1 d . . . . .
H17 H 0.271458 0.185447 0.281962 0.084 Uiso 1 1 calc R U . . .
C18 C 0.17926(18) 0.3189(4) 0.23925(13) 0.0718(8) Uani 1 1 d . . . . .
H18 H 0.174930 0.261306 0.207474 0.086 Uiso 1 1 calc R U . . .
C19 C 0.12695(17) 0.4491(4) 0.24034(12) 0.0692(8) Uani 1 1 d . . . . .
H19 H 0.086792 0.478434 0.209436 0.083 Uiso 1 1 calc R U . . .
C20 C 0.13330(16) 0.5343(4) 0.28556(12) 0.0654(8) Uani 1 1 d . . . . .
H20 H 0.097901 0.623845 0.285714 0.078 Uiso 1 1 calc R U . . .
C21 C 0.19204(15) 0.4911(3) 0.33236(11) 0.0566(7) Uani 1 1 d . . . . .
C22 C 0.20534(14) 0.5685(3) 0.38214(11) 0.0566(7) Uani 1 1 d . . . . .
C24 C 0.20575(14) 0.7411(3) 0.44943(11) 0.0553(7) Uani 1 1 d . . . . .
C31 C 0.37408(15) 0.3015(3) 0.46530(11) 0.0596(7) Uani 1 1 d . . . . .
C32 C 0.44983(15) 0.3075(4) 0.46699(11) 0.0622(7) Uani 1 1 d . . . . .
H32 H 0.462307 0.357141 0.438553 0.075 Uiso 1 1 calc R U . . .
C33 C 0.50852(15) 0.2439(4) 0.50860(11) 0.0637(8) Uani 1 1 d . . . . .
H33 H 0.560430 0.249832 0.508467 0.076 Uiso 1 1 calc R U . . .
C34 C 0.49202(15) 0.1721(3) 0.55024(11) 0.0580(7) Uani 1 1 d . . . . .
C35 C 0.41648(17) 0.1653(4) 0.54960(14) 0.0853(11) Uani 1 1 d . . . . .
H35 H 0.404166 0.115852 0.578110 0.102 Uiso 1 1 calc R U . . .
C36 C 0.35904(17) 0.2295(4) 0.50811(15) 0.0876(11) Uani 1 1 d . . . . .
H36 H 0.307261 0.224731 0.508549 0.105 Uiso 1 1 calc R U . . .
C38 C 0.62427(16) 0.1114(4) 0.59557(12) 0.0744(9) Uani 1 1 d . . . . .
H38A H 0.655752 0.046996 0.626006 0.112 Uiso 1 1 calc R U . . .
H38B H 0.641414 0.231622 0.598316 0.112 Uiso 1 1 calc R U . . .
H38C H 0.629912 0.060210 0.563861 0.112 Uiso 1 1 calc R U . . .
C41 C 0.10733(14) 0.8134(3) 0.36613(11) 0.0560(7) Uani 1 1 d . . . . .
C42 C 0.03236(14) 0.7649(4) 0.35868(11) 0.0613(7) Uani 1 1 d . . . . .
H42 H 0.021213 0.658008 0.371861 0.074 Uiso 1 1 calc R U . . .
C43 C -0.02697(16) 0.8739(4) 0.33163(12) 0.0732(9) Uani 1 1 d . . . . .
H43 H -0.079219 0.840953 0.325345 0.088 Uiso 1 1 calc R U . . .
C44 C -0.0097(2) 1.0296(5) 0.31403(13) 0.0860(10) Uani 1 1 d . . . . .
H44 H -0.050208 1.105149 0.296004 0.103 Uiso 1 1 calc R U . . .
C45 C 0.0654(2) 1.0771(4) 0.32219(14) 0.0901(11) Uani 1 1 d . . . . .
H45 H 0.076745 1.185178 0.309816 0.108 Uiso 1 1 calc R U . . .
C46 C 0.12420(17) 0.9690(4) 0.34817(13) 0.0763(9) Uani 1 1 d . . . . .
H46 H 0.176343 1.001511 0.353737 0.092 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
O38 C34 1.370(3) . ?
O38 C38 1.421(3) . ?
N15 C14 1.329(4) . ?
N15 C16 1.377(4) . ?
N23 C22 1.380(3) . ?
N23 C24 1.399(3) . ?
N23 C41 1.433(3) . ?
C11 C24 1.377(4) 7_566 ?
C11 C12 1.397(4) . ?
C11 H11 0.9500 . ?
C12 C24 1.423(3) . ?
C12 C13 1.449(4) . ?
C13 C22 1.405(4) . ?
C13 C14 1.409(4) . ?
C14 C31 1.489(4) . ?
C16 C17 1.416(4) . ?
C16 C21 1.418(4) . ?
C17 C18 1.359(4) . ?
C17 H17 0.9500 . ?
C18 C19 1.398(4) . ?
C18 H18 0.9500 . ?
C19 C20 1.363(4) . ?
C19 H19 0.9500 . ?
C20 C21 1.418(4) . ?
C20 H20 0.9500 . ?
C21 C22 1.424(4) . ?
C31 C32 1.370(4) . ?
C31 C36 1.389(4) . ?
C32 C33 1.378(4) . ?
C32 H32 0.9500 . ?
C33 C34 1.373(4) . ?
C33 H33 0.9500 . ?
C34 C35 1.375(4) . ?
C35 C36 1.366(4) . ?
C35 H35 0.9500 . ?
C36 H36 0.9500 . ?
C38 H38A 0.9800 . ?
C38 H38B 0.9800 . ?
C38 H38C 0.9800 . ?
C41 C42 1.372(3) . ?
C41 C46 1.373(4) . ?
C42 C43 1.388(4) . ?
C42 H42 0.9500 . ?
C43 C44 1.372(5) . ?
C43 H43 0.9500 . ?
C44 C45 1.369(4) . ?
C44 H44 0.9500 . ?
C45 C46 1.370(4) . ?
C45 H45 0.9500 . ?
C46 H46 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
C34 O38 C38 117.5(2) . . ?
C14 N15 C16 118.7(2) . . ?
C22 N23 C24 108.7(2) . . ?
C22 N23 C41 130.3(2) . . ?
C24 N23 C41 120.9(2) . . ?
C24 C11 C12 116.5(2) 7_566 . ?
C24 C11 H11 121.8 7_566 . ?
C12 C11 H11 121.8 . . ?
C11 C12 C24 119.3(3) . . ?
C11 C12 C13 134.8(2) . . ?
C24 C12 C13 105.8(2) . . ?
C22 C13 C14 119.4(3) . . ?
C22 C13 C12 107.5(2) . . ?
C14 C13 C12 133.0(3) . . ?
N15 C14 C13 121.7(3) . . ?
N15 C14 C31 116.9(2) . . ?
C13 C14 C31 121.4(3) . . ?
N15 C16 C17 116.6(3) . . ?
N15 C16 C21 125.0(3) . . ?
C17 C16 C21 118.4(3) . . ?
C18 C17 C16 121.2(3) . . ?
C18 C17 H17 119.4 . . ?
C16 C17 H17 119.4 . . ?
C17 C18 C19 120.4(3) . . ?
C17 C18 H18 119.8 . . ?
C19 C18 H18 119.8 . . ?
C20 C19 C18 120.3(3) . . ?
C20 C19 H19 119.9 . . ?
C18 C19 H19 119.9 . . ?
C19 C20 C21 120.9(3) . . ?
C19 C20 H20 119.6 . . ?
C21 C20 H20 119.6 . . ?
C16 C21 C20 118.7(3) . . ?
C16 C21 C22 114.3(3) . . ?
C20 C21 C22 126.9(3) . . ?
N23 C22 C13 109.2(2) . . ?
N23 C22 C21 130.0(2) . . ?
C13 C22 C21 120.8(2) . . ?
C11 C24 N23 127.0(2) 7_566 . ?
C11 C24 C12 124.2(2) 7_566 . ?
N23 C24 C12 108.8(2) . . ?
C32 C31 C36 116.6(3) . . ?
C32 C31 C14 121.4(3) . . ?
C36 C31 C14 122.0(2) . . ?
C31 C32 C33 122.1(3) . . ?
C31 C32 H32 118.9 . . ?
C33 C32 H32 118.9 . . ?
C34 C33 C32 120.1(3) . . ?
C34 C33 H33 120.0 . . ?
C32 C33 H33 120.0 . . ?
O38 C34 C33 125.0(2) . . ?
O38 C34 C35 116.1(3) . . ?
C33 C34 C35 118.9(3) . . ?
C36 C35 C34 120.3(3) . . ?
C36 C35 H35 119.9 . . ?
C34 C35 H35 119.9 . . ?
C35 C36 C31 122.0(3) . . ?
C35 C36 H36 119.0 . . ?
C31 C36 H36 119.0 . . ?
O38 C38 H38A 109.5 . . ?
O38 C38 H38B 109.5 . . ?
H38A C38 H38B 109.5 . . ?
O38 C38 H38C 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
C42 C41 C46 121.0(3) . . ?
C42 C41 N23 119.6(2) . . ?
C46 C41 N23 119.2(2) . . ?
C41 C42 C43 119.1(3) . . ?
C41 C42 H42 120.4 . . ?
C43 C42 H42 120.4 . . ?
C44 C43 C42 119.6(3) . . ?
C44 C43 H43 120.2 . . ?
C42 C43 H43 120.2 . . ?
C45 C44 C43 120.6(3) . . ?
C45 C44 H44 119.7 . . ?
C43 C44 H44 119.7 . . ?
C44 C45 C46 120.1(3) . . ?
C44 C45 H45 120.0 . . ?
C46 C45 H45 120.0 . . ?
C45 C46 C41 119.6(3) . . ?
C45 C46 H46 120.2 . . ?
C41 C46 H46 120.2 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C24 C11 C12 C24 1.3(4) 7_566 . . . ?
C24 C11 C12 C13 178.6(3) 7_566 . . . ?
C11 C12 C13 C22 -177.2(3) . . . . ?
C24 C12 C13 C22 0.3(3) . . . . ?
C11 C12 C13 C14 -1.2(5) . . . . ?
C24 C12 C13 C14 176.3(3) . . . . ?
C16 N15 C14 C13 -1.7(4) . . . . ?
C16 N15 C14 C31 178.8(2) . . . . ?
C22 C13 C14 N15 1.5(4) . . . . ?
C12 C13 C14 N15 -174.1(3) . . . . ?
C22 C13 C14 C31 -179.0(2) . . . . ?
C12 C13 C14 C31 5.4(4) . . . . ?
C14 N15 C16 C17 -179.2(2) . . . . ?
C14 N15 C16 C21 0.1(4) . . . . ?
N15 C16 C17 C18 178.1(3) . . . . ?
C21 C16 C17 C18 -1.2(4) . . . . ?
C16 C17 C18 C19 0.2(4) . . . . ?
C17 C18 C19 C20 1.0(4) . . . . ?
C18 C19 C20 C21 -1.0(4) . . . . ?
N15 C16 C21 C20 -178.1(2) . . . . ?
C17 C16 C21 C20 1.2(4) . . . . ?
N15 C16 C21 C22 1.7(4) . . . . ?
C17 C16 C21 C22 -179.0(2) . . . . ?
C19 C20 C21 C16 -0.1(4) . . . . ?
C19 C20 C21 C22 -179.9(3) . . . . ?
C24 N23 C22 C13 1.6(3) . . . . ?
C41 N23 C22 C13 178.3(2) . . . . ?
C24 N23 C22 C21 -176.4(3) . . . . ?
C41 N23 C22 C21 0.3(4) . . . . ?
C14 C13 C22 N23 -177.8(2) . . . . ?
C12 C13 C22 N23 -1.2(3) . . . . ?
C14 C13 C22 C21 0.4(4) . . . . ?
C12 C13 C22 C21 177.0(2) . . . . ?
C16 C21 C22 N23 175.9(2) . . . . ?
C20 C21 C22 N23 -4.3(4) . . . . ?
C16 C21 C22 C13 -1.9(3) . . . . ?
C20 C21 C22 C13 177.9(2) . . . . ?
C22 N23 C24 C11 178.7(2) . . . 7_566 ?
C41 N23 C24 C11 1.6(4) . . . 7_566 ?
C22 N23 C24 C12 -1.3(3) . . . . ?
C41 N23 C24 C12 -178.4(2) . . . . ?
C11 C12 C24 C11 -1.4(4) . . . 7_566 ?
C13 C12 C24 C11 -179.4(2) . . . 7_566 ?
C11 C12 C24 N23 178.6(2) . . . . ?
C13 C12 C24 N23 0.6(3) . . . . ?
N15 C14 C31 C32 61.5(4) . . . . ?
C13 C14 C31 C32 -118.0(3) . . . . ?
N15 C14 C31 C36 -119.4(3) . . . . ?
C13 C14 C31 C36 61.1(4) . . . . ?
C36 C31 C32 C33 0.7(4) . . . . ?
C14 C31 C32 C33 179.9(3) . . . . ?
C31 C32 C33 C34 -0.2(5) . . . . ?
C38 O38 C34 C33 0.8(4) . . . . ?
C38 O38 C34 C35 -179.3(3) . . . . ?
C32 C33 C34 O38 179.8(3) . . . . ?
C32 C33 C34 C35 -0.1(4) . . . . ?
O38 C34 C35 C36 180.0(3) . . . . ?
C33 C34 C35 C36 -0.1(5) . . . . ?
C34 C35 C36 C31 0.6(6) . . . . ?
C32 C31 C36 C35 -0.9(5) . . . . ?
C14 C31 C36 C35 179.9(3) . . . . ?
C22 N23 C41 C42 87.3(3) . . . . ?
C24 N23 C41 C42 -96.3(3) . . . . ?
C22 N23 C41 C46 -97.6(3) . . . . ?
C24 N23 C41 C46 78.8(3) . . . . ?
C46 C41 C42 C43 1.3(4) . . . . ?
N23 C41 C42 C43 176.3(3) . . . . ?
C41 C42 C43 C44 -1.6(5) . . . . ?
C42 C43 C44 C45 1.0(5) . . . . ?
C43 C44 C45 C46 0.0(6) . . . . ?
C44 C45 C46 C41 -0.3(6) . . . . ?
C42 C41 C46 C45 -0.4(5) . . . . ?
N23 C41 C46 C45 -175.4(3) . . . . ?

_refine_diff_density_max         0.156
_refine_diff_density_min         -0.163
_refine_diff_density_rms         0.038

####################################################################### 
# 
# 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_hek2
_database_code_depnum_ccdc_archive 'CCDC 2205010'
loop_
_audit_author_name
_audit_author_address
'Frank Rominger'
;Heidelberg University
Germany
;
_audit_update_record             
;
2022-09-02 deposited with the CCDC.	2022-10-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            '**2g** in manuscript'
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C56 H62 N4'
_chemical_formula_weight         791.09

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

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

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

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

_cell_length_a                   8.2372(2)
_cell_length_b                   17.6098(5)
_cell_length_c                   15.9665(4)
_cell_angle_alpha                90
_cell_angle_beta                 104.397(2)
_cell_angle_gamma                90
_cell_volume                     2243.30(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    16550
_cell_measurement_theta_min      5.02
_cell_measurement_theta_max      72.43

_exptl_crystal_description       pole
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.171
_exptl_crystal_F_000             852
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.251
_exptl_crystal_size_mid          0.052
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.514
_shelx_estimated_absorpt_T_min   0.882
_shelx_estimated_absorpt_T_max   0.975
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.728
_exptl_absorpt_correction_T_max  1.383
_exptl_absorpt_process_details   'STOE X-AREA LANA'
_exptl_absorpt_special_details   'X-Area LANA 1.70.0.0 (STOE, 2017)'
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Genix3D Cu HF'
_diffrn_measurement_device_type  'STOE Stadivari'
_diffrn_measurement_method       'rotation method, ω scans'
_diffrn_detector_area_resol_mean 5.81
_diffrn_reflns_number            14624
_diffrn_reflns_av_unetI/netI     0.0163
_diffrn_reflns_av_R_equivalents  0.0190
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         5.023
_diffrn_reflns_theta_max         72.077
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.962
_diffrn_measured_fraction_theta_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.962
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_point_group_measured_fraction_full 0.988
_reflns_number_total             4248
_reflns_number_gt                3404
_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       'X-Area Pilatus3_SV 1.31.144.0 (STOE, 2018)'
_computing_cell_refinement       'X-Area Recipe 1.33.0.0 (STOE, 2015)'
_computing_data_reduction        'X-Area Integrate 1.73.0.0 (STOE, 2018)'
_computing_structure_solution    'SHELXT-2014 (Sheldrick 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0568P)²+0.8053P] 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         4248
_refine_ls_number_parameters     272
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0619
_refine_ls_R_factor_gt           0.0470
_refine_ls_wR_factor_ref         0.1261
_refine_ls_wR_factor_gt          0.1155
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_restrained_S_all      1.061
_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
C11 C 0.55678(19) 0.48940(8) 0.59225(10) 0.0321(3) Uani 1 1 d . . . . .
H11 H 0.592646 0.481859 0.652977 0.038 Uiso 1 1 calc R U . . .
C12 C 0.65758(19) 0.52624(8) 0.54613(9) 0.0308(3) Uani 1 1 d . . . . .
C13 C 0.82224(19) 0.56052(8) 0.56915(9) 0.0311(3) Uani 1 1 d . . . . .
C14 C 0.94416(19) 0.57050(9) 0.64876(10) 0.0333(3) Uani 1 1 d . . . . .
N15 N 1.09066(16) 0.60204(7) 0.65259(9) 0.0361(3) Uani 1 1 d . . . . .
C16 C 1.1274(2) 0.62526(9) 0.57680(10) 0.0347(3) Uani 1 1 d . . . . .
C17 C 1.2898(2) 0.65440(9) 0.58376(12) 0.0416(4) Uani 1 1 d . . . . .
H17 H 1.365696 0.658623 0.639117 0.050 Uiso 1 1 calc R U . . .
C18 C 1.3396(2) 0.67667(10) 0.51185(12) 0.0446(4) Uani 1 1 d . . . . .
H18 H 1.449861 0.695593 0.517582 0.054 Uiso 1 1 calc R U . . .
C19 C 1.2289(2) 0.67167(10) 0.43004(12) 0.0432(4) Uani 1 1 d . . . . .
H19 H 1.264513 0.687338 0.380522 0.052 Uiso 1 1 calc R U . . .
C20 C 1.0699(2) 0.64446(9) 0.42054(11) 0.0393(4) Uani 1 1 d . . . . .
H20 H 0.995756 0.641688 0.364569 0.047 Uiso 1 1 calc R U . . .
C21 C 1.01466(19) 0.62030(8) 0.49371(10) 0.0333(3) Uani 1 1 d . . . . .
C22 C 0.85618(19) 0.58762(8) 0.49300(10) 0.0315(3) Uani 1 1 d . . . . .
N23 N 0.72088(16) 0.57315(7) 0.42414(8) 0.0331(3) Uani 1 1 d . . . . .
C24 C 0.59784(19) 0.53544(8) 0.45535(10) 0.0314(3) Uani 1 1 d . . . . .
C31 C 0.9069(2) 0.54741(10) 0.73291(10) 0.0384(4) Uani 1 1 d . . . . .
H31A H 1.012426 0.546981 0.779039 0.046 Uiso 1 1 calc R U . . .
H31B H 0.860503 0.495269 0.727317 0.046 Uiso 1 1 calc R U . . .
C32 C 0.7821(2) 0.60124(10) 0.75866(11) 0.0420(4) Uani 1 1 d . . . . .
H32A H 0.837205 0.650944 0.774780 0.050 Uiso 1 1 calc R U . . .
H32B H 0.686348 0.609422 0.708013 0.050 Uiso 1 1 calc R U . . .
C33 C 0.7160(2) 0.57211(11) 0.83378(11) 0.0457(4) Uani 1 1 d . . . . .
H33A H 0.671014 0.520187 0.820219 0.055 Uiso 1 1 calc R U . . .
H33B H 0.809907 0.569049 0.886197 0.055 Uiso 1 1 calc R U . . .
C34 C 0.5797(3) 0.62225(11) 0.85253(13) 0.0513(5) Uani 1 1 d . . . . .
H34A H 0.487589 0.626191 0.799407 0.062 Uiso 1 1 calc R U . . .
H34B H 0.625946 0.673872 0.866801 0.062 Uiso 1 1 calc R U . . .
C35 C 0.5076(2) 0.59462(11) 0.92575(12) 0.0477(4) Uani 1 1 d . . . . .
H35A H 0.472705 0.540969 0.914977 0.057 Uiso 1 1 calc R U . . .
H35B H 0.596247 0.596558 0.980459 0.057 Uiso 1 1 calc R U . . .
C36 C 0.3590(3) 0.64084(12) 0.93607(13) 0.0543(5) Uani 1 1 d . . . . .
H36A H 0.275633 0.642882 0.879513 0.065 Uiso 1 1 calc R U . . .
H36B H 0.397099 0.693443 0.951729 0.065 Uiso 1 1 calc R U . . .
C37 C 0.2727(3) 0.61119(11) 1.00341(13) 0.0520(5) Uani 1 1 d . . . . .
H37A H 0.232272 0.558907 0.987703 0.062 Uiso 1 1 calc R U . . .
H37B H 0.355166 0.608962 1.060261 0.062 Uiso 1 1 calc R U . . .
C38 C 0.1259(3) 0.66042(13) 1.01111(14) 0.0616(6) Uani 1 1 d . . . . .
H38A H 0.040851 0.659733 0.955074 0.074 Uiso 1 1 calc R U . . .
H38B H 0.165597 0.713408 1.022260 0.074 Uiso 1 1 calc R U . . .
C39 C 0.0425(3) 0.63632(14) 1.08193(16) 0.0683(6) Uani 1 1 d . . . . .
H39A H -0.069761 0.660073 1.070808 0.082 Uiso 1 1 calc R U . . .
H39B H 0.026654 0.580564 1.079215 0.082 Uiso 1 1 calc R U . . .
C40 C 0.1414(4) 0.65777(16) 1.17202(17) 0.0819(8) Uani 1 1 d . . . . .
H40A H 0.081548 0.640361 1.214378 0.123 Uiso 1 1 calc R U . . .
H40B H 0.154563 0.713063 1.175938 0.123 Uiso 1 1 calc R U . . .
H40C H 0.252146 0.633765 1.184051 0.123 Uiso 1 1 calc R U . . .
C41 C 0.69100(19) 0.60533(9) 0.33908(10) 0.0326(3) Uani 1 1 d . . . . .
C42 C 0.7048(2) 0.56087(9) 0.26980(10) 0.0388(4) Uani 1 1 d . . . . .
H42 H 0.725909 0.507932 0.276973 0.047 Uiso 1 1 calc R U . . .
C43 C 0.6872(2) 0.59486(11) 0.18956(11) 0.0486(4) Uani 1 1 d . . . . .
H43 H 0.697664 0.564999 0.141621 0.058 Uiso 1 1 calc R U . . .
C44 C 0.6548(2) 0.67145(11) 0.17882(12) 0.0504(5) Uani 1 1 d . . . . .
H44 H 0.644326 0.694231 0.123793 0.060 Uiso 1 1 calc R U . . .
C45 C 0.6375(2) 0.71518(11) 0.24780(12) 0.0498(5) Uani 1 1 d . . . . .
H45 H 0.614334 0.767925 0.240224 0.060 Uiso 1 1 calc R U . . .
C46 C 0.6541(2) 0.68189(9) 0.32828(11) 0.0420(4) Uani 1 1 d . . . . .
H46 H 0.640229 0.711542 0.375716 0.050 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
C11 C24 1.382(2) 3_666 ?
C11 C12 1.399(2) . ?
C11 H11 0.9500 . ?
C12 C24 1.419(2) . ?
C12 C13 1.446(2) . ?
C13 C22 1.398(2) . ?
C13 C14 1.421(2) . ?
C14 N15 1.316(2) . ?
C14 C31 1.507(2) . ?
N15 C16 1.380(2) . ?
C16 C17 1.411(2) . ?
C16 C21 1.420(2) . ?
C17 C18 1.369(2) . ?
C17 H17 0.9500 . ?
C18 C19 1.398(3) . ?
C18 H18 0.9500 . ?
C19 C20 1.368(2) . ?
C19 H19 0.9500 . ?
C20 C21 1.420(2) . ?
C20 H20 0.9500 . ?
C21 C22 1.424(2) . ?
C22 N23 1.381(2) . ?
N23 C24 1.4027(19) . ?
N23 C41 1.4352(19) . ?
C31 C32 1.527(2) . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?
C32 C33 1.524(2) . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
C33 C34 1.515(3) . ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?
C34 C35 1.517(2) . ?
C34 H34A 0.9900 . ?
C34 H34B 0.9900 . ?
C35 C36 1.513(3) . ?
C35 H35A 0.9900 . ?
C35 H35B 0.9900 . ?
C36 C37 1.521(3) . ?
C36 H36A 0.9900 . ?
C36 H36B 0.9900 . ?
C37 C38 1.517(3) . ?
C37 H37A 0.9900 . ?
C37 H37B 0.9900 . ?
C38 C39 1.522(3) . ?
C38 H38A 0.9900 . ?
C38 H38B 0.9900 . ?
C39 C40 1.514(4) . ?
C39 H39A 0.9900 . ?
C39 H39B 0.9900 . ?
C40 H40A 0.9800 . ?
C40 H40B 0.9800 . ?
C40 H40C 0.9800 . ?
C41 C42 1.383(2) . ?
C41 C46 1.383(2) . ?
C42 C43 1.389(2) . ?
C42 H42 0.9500 . ?
C43 C44 1.377(3) . ?
C43 H43 0.9500 . ?
C44 C45 1.380(3) . ?
C44 H44 0.9500 . ?
C45 C46 1.388(2) . ?
C45 H45 0.9500 . ?
C46 H46 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
C24 C11 C12 116.34(14) 3_666 . ?
C24 C11 H11 121.8 3_666 . ?
C12 C11 H11 121.8 . . ?
C11 C12 C24 119.34(14) . . ?
C11 C12 C13 134.57(14) . . ?
C24 C12 C13 106.08(12) . . ?
C22 C13 C14 119.08(14) . . ?
C22 C13 C12 107.42(13) . . ?
C14 C13 C12 133.50(13) . . ?
N15 C14 C13 121.97(14) . . ?
N15 C14 C31 117.41(14) . . ?
C13 C14 C31 120.58(14) . . ?
C14 N15 C16 118.87(14) . . ?
N15 C16 C17 116.68(15) . . ?
N15 C16 C21 124.44(14) . . ?
C17 C16 C21 118.87(14) . . ?
C18 C17 C16 120.93(16) . . ?
C18 C17 H17 119.5 . . ?
C16 C17 H17 119.5 . . ?
C17 C18 C19 120.25(16) . . ?
C17 C18 H18 119.9 . . ?
C19 C18 H18 119.9 . . ?
C20 C19 C18 120.68(15) . . ?
C20 C19 H19 119.7 . . ?
C18 C19 H19 119.7 . . ?
C19 C20 C21 120.51(16) . . ?
C19 C20 H20 119.7 . . ?
C21 C20 H20 119.7 . . ?
C20 C21 C16 118.76(14) . . ?
C20 C21 C22 126.51(15) . . ?
C16 C21 C22 114.68(13) . . ?
N23 C22 C13 109.46(13) . . ?
N23 C22 C21 129.62(13) . . ?
C13 C22 C21 120.82(14) . . ?
C22 N23 C24 108.42(12) . . ?
C22 N23 C41 126.53(12) . . ?
C24 N23 C41 123.64(13) . . ?
C11 C24 N23 127.08(14) 3_666 . ?
C11 C24 C12 124.31(13) 3_666 . ?
N23 C24 C12 108.61(13) . . ?
C14 C31 C32 111.87(14) . . ?
C14 C31 H31A 109.2 . . ?
C32 C31 H31A 109.2 . . ?
C14 C31 H31B 109.2 . . ?
C32 C31 H31B 109.2 . . ?
H31A C31 H31B 107.9 . . ?
C33 C32 C31 113.52(14) . . ?
C33 C32 H32A 108.9 . . ?
C31 C32 H32A 108.9 . . ?
C33 C32 H32B 108.9 . . ?
C31 C32 H32B 108.9 . . ?
H32A C32 H32B 107.7 . . ?
C34 C33 C32 112.75(15) . . ?
C34 C33 H33A 109.0 . . ?
C32 C33 H33A 109.0 . . ?
C34 C33 H33B 109.0 . . ?
C32 C33 H33B 109.0 . . ?
H33A C33 H33B 107.8 . . ?
C33 C34 C35 114.61(15) . . ?
C33 C34 H34A 108.6 . . ?
C35 C34 H34A 108.6 . . ?
C33 C34 H34B 108.6 . . ?
C35 C34 H34B 108.6 . . ?
H34A C34 H34B 107.6 . . ?
C36 C35 C34 113.19(15) . . ?
C36 C35 H35A 108.9 . . ?
C34 C35 H35A 108.9 . . ?
C36 C35 H35B 108.9 . . ?
C34 C35 H35B 108.9 . . ?
H35A C35 H35B 107.8 . . ?
C35 C36 C37 115.17(15) . . ?
C35 C36 H36A 108.5 . . ?
C37 C36 H36A 108.5 . . ?
C35 C36 H36B 108.5 . . ?
C37 C36 H36B 108.5 . . ?
H36A C36 H36B 107.5 . . ?
C38 C37 C36 112.52(16) . . ?
C38 C37 H37A 109.1 . . ?
C36 C37 H37A 109.1 . . ?
C38 C37 H37B 109.1 . . ?
C36 C37 H37B 109.1 . . ?
H37A C37 H37B 107.8 . . ?
C37 C38 C39 114.64(18) . . ?
C37 C38 H38A 108.6 . . ?
C39 C38 H38A 108.6 . . ?
C37 C38 H38B 108.6 . . ?
C39 C38 H38B 108.6 . . ?
H38A C38 H38B 107.6 . . ?
C40 C39 C38 113.6(2) . . ?
C40 C39 H39A 108.8 . . ?
C38 C39 H39A 108.8 . . ?
C40 C39 H39B 108.8 . . ?
C38 C39 H39B 108.8 . . ?
H39A C39 H39B 107.7 . . ?
C39 C40 H40A 109.5 . . ?
C39 C40 H40B 109.5 . . ?
H40A C40 H40B 109.5 . . ?
C39 C40 H40C 109.5 . . ?
H40A C40 H40C 109.5 . . ?
H40B C40 H40C 109.5 . . ?
C42 C41 C46 120.75(14) . . ?
C42 C41 N23 120.31(14) . . ?
C46 C41 N23 118.91(14) . . ?
C41 C42 C43 118.92(16) . . ?
C41 C42 H42 120.5 . . ?
C43 C42 H42 120.5 . . ?
C44 C43 C42 120.63(17) . . ?
C44 C43 H43 119.7 . . ?
C42 C43 H43 119.7 . . ?
C43 C44 C45 120.15(16) . . ?
C43 C44 H44 119.9 . . ?
C45 C44 H44 119.9 . . ?
C44 C45 C46 119.83(17) . . ?
C44 C45 H45 120.1 . . ?
C46 C45 H45 120.1 . . ?
C41 C46 C45 119.67(16) . . ?
C41 C46 H46 120.2 . . ?
C45 C46 H46 120.2 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C24 C11 C12 C24 -0.4(2) 3_666 . . . ?
C24 C11 C12 C13 179.64(16) 3_666 . . . ?
C11 C12 C13 C22 179.15(16) . . . . ?
C24 C12 C13 C22 -0.80(16) . . . . ?
C11 C12 C13 C14 -0.9(3) . . . . ?
C24 C12 C13 C14 179.13(16) . . . . ?
C22 C13 C14 N15 -2.5(2) . . . . ?
C12 C13 C14 N15 177.57(15) . . . . ?
C22 C13 C14 C31 175.34(14) . . . . ?
C12 C13 C14 C31 -4.6(3) . . . . ?
C13 C14 N15 C16 -0.8(2) . . . . ?
C31 C14 N15 C16 -178.69(14) . . . . ?
C14 N15 C16 C17 -176.18(14) . . . . ?
C14 N15 C16 C21 2.6(2) . . . . ?
N15 C16 C17 C18 177.96(15) . . . . ?
C21 C16 C17 C18 -0.9(2) . . . . ?
C16 C17 C18 C19 0.8(3) . . . . ?
C17 C18 C19 C20 -0.1(3) . . . . ?
C18 C19 C20 C21 -0.4(3) . . . . ?
C19 C20 C21 C16 0.3(2) . . . . ?
C19 C20 C21 C22 -176.83(16) . . . . ?
N15 C16 C21 C20 -178.38(14) . . . . ?
C17 C16 C21 C20 0.4(2) . . . . ?
N15 C16 C21 C22 -0.9(2) . . . . ?
C17 C16 C21 C22 177.80(14) . . . . ?
C14 C13 C22 N23 -179.03(13) . . . . ?
C12 C13 C22 N23 0.91(17) . . . . ?
C14 C13 C22 C21 4.1(2) . . . . ?
C12 C13 C22 C21 -175.91(13) . . . . ?
C20 C21 C22 N23 -1.3(3) . . . . ?
C16 C21 C22 N23 -178.55(15) . . . . ?
C20 C21 C22 C13 174.76(15) . . . . ?
C16 C21 C22 C13 -2.4(2) . . . . ?
C13 C22 N23 C24 -0.66(17) . . . . ?
C21 C22 N23 C24 175.80(15) . . . . ?
C13 C22 N23 C41 166.06(14) . . . . ?
C21 C22 N23 C41 -17.5(3) . . . . ?
C22 N23 C24 C11 -179.87(15) . . . 3_666 ?
C41 N23 C24 C11 12.9(2) . . . 3_666 ?
C22 N23 C24 C12 0.14(17) . . . . ?
C41 N23 C24 C12 -167.05(13) . . . . ?
C11 C12 C24 C11 0.5(3) . . . 3_666 ?
C13 C12 C24 C11 -179.59(14) . . . 3_666 ?
C11 C12 C24 N23 -179.55(13) . . . . ?
C13 C12 C24 N23 0.41(16) . . . . ?
N15 C14 C31 C32 105.81(17) . . . . ?
C13 C14 C31 C32 -72.13(19) . . . . ?
C14 C31 C32 C33 169.18(15) . . . . ?
C31 C32 C33 C34 -174.23(16) . . . . ?
C32 C33 C34 C35 178.86(16) . . . . ?
C33 C34 C35 C36 -173.45(18) . . . . ?
C34 C35 C36 C37 174.85(18) . . . . ?
C35 C36 C37 C38 179.49(19) . . . . ?
C36 C37 C38 C39 -176.0(2) . . . . ?
C37 C38 C39 C40 76.2(3) . . . . ?
C22 N23 C41 C42 109.41(18) . . . . ?
C24 N23 C41 C42 -85.76(19) . . . . ?
C22 N23 C41 C46 -68.3(2) . . . . ?
C24 N23 C41 C46 96.48(18) . . . . ?
C46 C41 C42 C43 2.4(2) . . . . ?
N23 C41 C42 C43 -175.32(15) . . . . ?
C41 C42 C43 C44 -0.7(3) . . . . ?
C42 C43 C44 C45 -0.7(3) . . . . ?
C43 C44 C45 C46 0.5(3) . . . . ?
C42 C41 C46 C45 -2.7(3) . . . . ?
N23 C41 C46 C45 175.09(15) . . . . ?
C44 C45 C46 C41 1.2(3) . . . . ?

_refine_diff_density_max         0.484
_refine_diff_density_min         -0.209
_refine_diff_density_rms         0.051

