# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2019

####################################################################### 
# 
# 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_dan9426
_database_code_depnum_ccdc_archive 'CCDC 1913072'
loop_
_audit_author_name
_audit_author_address
'Constantin G. Daniliuc'
;Organisch Chemisches Institut WWU University of Muenster
Germany
;
_audit_update_record             
;
2019-04-30 deposited with the CCDC.	2019-06-27 downloaded from the CCDC.
;

_audit_creation_method           'APEX3 v2016.1-0'
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H29 N3'
_chemical_formula_iupac          ?
_chemical_formula_weight         359.50

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   13.0757(4)
_cell_length_b                   11.9628(4)
_cell_length_c                   13.2380(5)
_cell_angle_alpha                90
_cell_angle_beta                 92.8130(10)
_cell_angle_gamma                90
_cell_volume                     2068.22(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9959
_cell_measurement_theta_min      3.3841
_cell_measurement_theta_max      66.9276
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.249
_exptl_crystal_size_mid          0.138
_exptl_crystal_size_min          0.084
_exptl_crystal_density_diffrn    1.155
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             776

_exptl_absorpt_coefficient_mu    0.521
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
Bruker AXS (2014). SADABS, Version 2014/5, Bruker AXS Inc., Madison, Wisconsin,
USA.
;
_exptl_absorpt_correction_T_min  0.90
_exptl_absorpt_correction_T_max  0.96

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'Cu ImS'
_diffrn_source_type              'micro focus tube'

_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  'MX mirror'

_diffrn_measurement_device_type  'Bruker D8 Venture PHOTON 100 CMOS'
_diffrn_measurement_method       'omega and phi scans'

_diffrn_detector_area_resol_mean 10.4167

_diffrn_reflns_number            41845
_diffrn_reflns_av_R_equivalents  0.0431
_diffrn_reflns_av_unetI/netI     0.0185
_diffrn_reflns_theta_min         3.38
_diffrn_reflns_theta_max         66.92
_diffrn_reflns_theta_full        66.92
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15

_refine_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.

One disordered over two positions iPr group was found in 
the asymmetrical unit. Several restraints (SADI, SAME, ISOR
and SIMU) were used in order to improve refinement stability.

The hydrogen atoms at N3 were refined freely.
;

_reflns_number_total             3670
_reflns_number_gt                3268
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0418
_refine_ls_R_factor_gt           0.0365
_refine_ls_wR_factor_gt          0.0879
_refine_ls_wR_factor_ref         0.0913
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_restrained_S_all      1.074
_refine_ls_number_reflns         3670
_refine_ls_number_parameters     279
_refine_ls_number_restraints     37
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0443P)²+0.6431P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.152
_refine_diff_density_min         -0.204
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'

_computing_data_collection       
;

APEX3 v2016.1-0 (Bruker AXS Inc., 2016)
;
_computing_cell_refinement       'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_data_reduction        'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'XP (Sheldrick, 2014)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N N1 0.32035(7) 0.51375(8) 0.66262(7) 0.0156(2) Uani d . . . 1.0 . .
N N2 0.16496(7) 0.25480(8) 0.88400(7) 0.0153(2) Uani d . . . 1.0 . .
N N3 0.19524(8) 0.35672(9) 0.58449(7) 0.0202(2) Uani d . . . 1.0 . .
H H3A 0.2470(12) 0.4126(14) 0.5766(11) 0.031(4) Uiso d . . . 1.0 . .
H H3B 0.1736(12) 0.3130(14) 0.5311(12) 0.038(4) Uiso d . . . 1.0 . .
C C1 0.27433(8) 0.49990(9) 0.74532(8) 0.0145(2) Uani d . . . 1.0 . .
C C2 0.26296(10) 0.59562(10) 0.81843(8) 0.0205(3) Uani d . . . 1.0 . .
H H2A 0.3293 0.6111 0.8534 0.031 Uiso calc U . R 1.0 . .
H H2B 0.213 0.5755 0.8681 0.031 Uiso calc U . R 1.0 . .
H H2C 0.2393 0.6623 0.7812 0.031 Uiso calc U . R 1.0 . .
C C11 0.36550(9) 0.61860(10) 0.63988(8) 0.0162(2) Uani d . . . 1.0 . .
C C12 0.30527(9) 0.70397(10) 0.59465(8) 0.0176(3) Uani d . . . 1.0 . .
C C13 0.35446(10) 0.80161(10) 0.56630(9) 0.0226(3) Uani d . . . 1.0 . .
H H13 0.3153 0.8606 0.5359 0.027 Uiso calc U . R 1.0 . .
C C14 0.45916(10) 0.81421(11) 0.58149(10) 0.0283(3) Uani d . . . 1.0 . .
H H14 0.4914 0.8808 0.5605 0.034 Uiso calc U . R 1.0 . .
C C15 0.51693(10) 0.72974(12) 0.62730(10) 0.0270(3) Uani d . . . 1.0 . .
H H15 0.5887 0.7396 0.6382 0.032 Uiso calc U . R 1.0 . .
C C16 0.47201(9) 0.63058(10) 0.65780(8) 0.0204(3) Uani d . . . 1.0 . .
C C17 0.19013(9) 0.69126(10) 0.57510(9) 0.0195(3) Uani d . . . 1.0 . .
H H17 0.1665 0.6316 0.6214 0.023 Uiso calc U . R 1.0 . .
C C18 0.16454(10) 0.65246(11) 0.46637(9) 0.0262(3) Uani d . . . 1.0 . .
H H18A 0.1869 0.7093 0.4189 0.039 Uiso calc U . R 1.0 . .
H H18B 0.0905 0.6414 0.4566 0.039 Uiso calc U . R 1.0 . .
H H18C 0.1999 0.5819 0.4541 0.039 Uiso calc U . R 1.0 . .
C C19 0.13168(10) 0.79827(11) 0.59862(11) 0.0282(3) Uani d . . . 1.0 . .
H H19A 0.152 0.8238 0.667 0.042 Uiso calc U . R 1.0 . .
H H19B 0.0579 0.7831 0.5943 0.042 Uiso calc U . R 1.0 . .
H H19C 0.1477 0.8563 0.5496 0.042 Uiso calc U . R 1.0 . .
C C20 0.53506(9) 0.53723(11) 0.70802(9) 0.0257(3) Uani d . . D 1.0 . .
H H20 0.4922 0.5043 0.761 0.031 Uiso calc U P R 0.740(7) A 1
H H20A 0.4905 0.4748 0.7301 0.031 Uiso calc U P R 0.260(7) A 2
C C21 0.5553(2) 0.4420(2) 0.63186(17) 0.0418(8) Uani d U P D 0.740(7) A 1
H H21A 0.5977 0.4704 0.5785 0.063 Uiso calc U P R 0.740(7) A 1
H H21B 0.4899 0.415 0.6017 0.063 Uiso calc U P R 0.740(7) A 1
H H21C 0.591 0.3804 0.6673 0.063 Uiso calc U P R 0.740(7) A 1
C C22 0.6342(2) 0.5730(3) 0.7611(3) 0.0442(8) Uani d U P D 0.740(7) A 1
H H22A 0.6822 0.5975 0.7109 0.066 Uiso calc U P R 0.740(7) A 1
H H22B 0.6639 0.51 0.7996 0.066 Uiso calc U P R 0.740(7) A 1
H H22C 0.6212 0.6349 0.8072 0.066 Uiso calc U P R 0.740(7) A 1
C C21A 0.6122(8) 0.4966(8) 0.6339(5) 0.051(3) Uani d U P D 0.260(7) A 2
H H21D 0.5761 0.4729 0.571 0.076 Uiso calc U P R 0.260(7) A 2
H H21E 0.6507 0.4334 0.6635 0.076 Uiso calc U P R 0.260(7) A 2
H H21F 0.6596 0.5574 0.6196 0.076 Uiso calc U P R 0.260(7) A 2
C C22A 0.5972(7) 0.5920(6) 0.8013(6) 0.0361(19) Uani d U P D 0.260(7) A 2
H H22D 0.6432 0.6497 0.7769 0.054 Uiso calc U P R 0.260(7) A 2
H H22E 0.6375 0.5343 0.8376 0.054 Uiso calc U P R 0.260(7) A 2
H H22F 0.5493 0.6259 0.847 0.054 Uiso calc U P R 0.260(7) A 2
C C31 0.22479(8) 0.39038(9) 0.76355(8) 0.0135(2) Uani d . . . 1.0 . .
C C32 0.18320(8) 0.32653(9) 0.68119(8) 0.0142(2) Uani d . . . 1.0 . .
C C33 0.12379(8) 0.22883(9) 0.70316(8) 0.0140(2) Uani d . . . 1.0 . .
C C34 0.07360(8) 0.16265(10) 0.62705(8) 0.0170(2) Uani d . . . 1.0 . .
H H34 0.0764 0.184 0.5581 0.02 Uiso calc U . R 1.0 . .
C C35 0.02113(9) 0.06816(10) 0.65178(9) 0.0201(3) Uani d . . . 1.0 . .
H H35 -0.0122 0.0245 0.6 0.024 Uiso calc U . R 1.0 . .
C C36 0.01638(9) 0.03545(10) 0.75372(9) 0.0213(3) Uani d . . . 1.0 . .
H H36 -0.019 -0.0309 0.7704 0.026 Uiso calc U . R 1.0 . .
C C37 0.06266(9) 0.09922(10) 0.82866(9) 0.0192(3) Uani d . . . 1.0 . .
H H37 0.058 0.0774 0.8973 0.023 Uiso calc U . R 1.0 . .
C C38 0.11724(8) 0.19698(9) 0.80531(8) 0.0146(2) Uani d . . . 1.0 . .
C C39 0.21619(8) 0.34681(9) 0.86300(8) 0.0137(2) Uani d . . . 1.0 . .
C C40 0.27160(9) 0.39752(10) 0.95519(8) 0.0183(2) Uani d . . . 1.0 . .
H H40A 0.2249 0.4472 0.9896 0.027 Uiso calc U . R 1.0 . .
H H40B 0.3308 0.4404 0.9341 0.027 Uiso calc U . R 1.0 . .
H H40C 0.295 0.3378 1.0014 0.027 Uiso calc U . R 1.0 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N1 C1 . 1.2856(14) ?
N1 C11 . 1.4247(14) ?
N2 C39 . 1.3250(15) ?
N2 C38 . 1.3746(15) ?
N3 C32 . 1.3467(14) ?
N3 H3A . 0.960(16) ?
N3 H3B . 0.913(17) ?
C1 C31 . 1.4865(15) ?
C1 C2 . 1.5113(15) ?
C2 H2A . 0.98 ?
C2 H2B . 0.98 ?
C2 H2C . 0.98 ?
C11 C12 . 1.4055(17) ?
C11 C16 . 1.4085(16) ?
C12 C13 . 1.3937(16) ?
C12 C17 . 1.5226(16) ?
C13 C14 . 1.3822(18) ?
C13 H13 . 0.95 ?
C14 C15 . 1.3835(19) ?
C14 H14 . 0.95 ?
C15 C16 . 1.3923(18) ?
C15 H15 . 0.95 ?
C16 C20 . 1.5215(17) ?
C17 C19 . 1.5307(17) ?
C17 C18 . 1.5337(17) ?
C17 H17 . 1.0 ?
C18 H18A . 0.98 ?
C18 H18B . 0.98 ?
C18 H18C . 0.98 ?
C19 H19A . 0.98 ?
C19 H19B . 0.98 ?
C19 H19C . 0.98 ?
C20 C22 . 1.506(3) ?
C20 C21A . 1.521(6) ?
C20 C21 . 1.553(3) ?
C20 C22A . 1.586(7) ?
C20 H20 . 1.0 ?
C20 H20A . 1.0 ?
C21 H21A . 0.98 ?
C21 H21B . 0.98 ?
C21 H21C . 0.98 ?
C22 H22A . 0.98 ?
C22 H22B . 0.98 ?
C22 H22C . 0.98 ?
C21A H21D . 0.98 ?
C21A H21E . 0.98 ?
C21A H21F . 0.98 ?
C22A H22D . 0.98 ?
C22A H22E . 0.98 ?
C22A H22F . 0.98 ?
C31 C32 . 1.4177(15) ?
C31 C39 . 1.4255(15) ?
C32 C33 . 1.4410(16) ?
C33 C38 . 1.4116(15) ?
C33 C34 . 1.4169(16) ?
C34 C35 . 1.3703(17) ?
C34 H34 . 0.95 ?
C35 C36 . 1.4093(17) ?
C35 H35 . 0.95 ?
C36 C37 . 1.3687(17) ?
C36 H36 . 0.95 ?
C37 C38 . 1.4121(16) ?
C37 H37 . 0.95 ?
C39 C40 . 1.5152(15) ?
C40 H40A . 0.98 ?
C40 H40B . 0.98 ?
C40 H40C . 0.98 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C1 N1 C11 . . 120.63(9) ?
C39 N2 C38 . . 118.32(9) ?
C32 N3 H3A . . 113.9(9) ?
C32 N3 H3B . . 122.4(10) ?
H3A N3 H3B . . 120.5(13) ?
N1 C1 C31 . . 118.54(10) ?
N1 C1 C2 . . 120.84(10) ?
C31 C1 C2 . . 120.43(9) ?
C1 C2 H2A . . 109.5 ?
C1 C2 H2B . . 109.5 ?
H2A C2 H2B . . 109.5 ?
C1 C2 H2C . . 109.5 ?
H2A C2 H2C . . 109.5 ?
H2B C2 H2C . . 109.5 ?
C12 C11 C16 . . 121.77(11) ?
C12 C11 N1 . . 120.03(10) ?
C16 C11 N1 . . 118.07(10) ?
C13 C12 C11 . . 117.86(11) ?
C13 C12 C17 . . 120.22(11) ?
C11 C12 C17 . . 121.91(10) ?
C14 C13 C12 . . 121.27(12) ?
C14 C13 H13 . . 119.4 ?
C12 C13 H13 . . 119.4 ?
C13 C14 C15 . . 119.98(12) ?
C13 C14 H14 . . 120.0 ?
C15 C14 H14 . . 120.0 ?
C14 C15 C16 . . 121.35(11) ?
C14 C15 H15 . . 119.3 ?
C16 C15 H15 . . 119.3 ?
C15 C16 C11 . . 117.74(11) ?
C15 C16 C20 . . 121.66(11) ?
C11 C16 C20 . . 120.59(11) ?
C12 C17 C19 . . 112.42(10) ?
C12 C17 C18 . . 110.98(10) ?
C19 C17 C18 . . 110.84(10) ?
C12 C17 H17 . . 107.4 ?
C19 C17 H17 . . 107.4 ?
C18 C17 H17 . . 107.4 ?
C17 C18 H18A . . 109.5 ?
C17 C18 H18B . . 109.5 ?
H18A C18 H18B . . 109.5 ?
C17 C18 H18C . . 109.5 ?
H18A C18 H18C . . 109.5 ?
H18B C18 H18C . . 109.5 ?
C17 C19 H19A . . 109.5 ?
C17 C19 H19B . . 109.5 ?
H19A C19 H19B . . 109.5 ?
C17 C19 H19C . . 109.5 ?
H19A C19 H19C . . 109.5 ?
H19B C19 H19C . . 109.5 ?
C22 C20 C16 . . 115.51(15) ?
C21A C20 C16 . . 108.4(3) ?
C22 C20 C21 . . 109.94(18) ?
C16 C20 C21 . . 111.16(12) ?
C21A C20 C22A . . 107.6(5) ?
C16 C20 C22A . . 106.4(3) ?
C22 C20 H20 . . 106.6 ?
C16 C20 H20 . . 106.6 ?
C21 C20 H20 . . 106.6 ?
C21A C20 H20A . . 111.4 ?
C16 C20 H20A . . 111.4 ?
C22A C20 H20A . . 111.4 ?
C20 C21 H21A . . 109.5 ?
C20 C21 H21B . . 109.5 ?
H21A C21 H21B . . 109.5 ?
C20 C21 H21C . . 109.5 ?
H21A C21 H21C . . 109.5 ?
H21B C21 H21C . . 109.5 ?
C20 C22 H22A . . 109.5 ?
C20 C22 H22B . . 109.5 ?
H22A C22 H22B . . 109.5 ?
C20 C22 H22C . . 109.5 ?
H22A C22 H22C . . 109.5 ?
H22B C22 H22C . . 109.5 ?
C20 C21A H21D . . 109.5 ?
C20 C21A H21E . . 109.5 ?
H21D C21A H21E . . 109.5 ?
C20 C21A H21F . . 109.5 ?
H21D C21A H21F . . 109.5 ?
H21E C21A H21F . . 109.5 ?
C20 C22A H22D . . 109.5 ?
C20 C22A H22E . . 109.5 ?
H22D C22A H22E . . 109.5 ?
C20 C22A H22F . . 109.5 ?
H22D C22A H22F . . 109.5 ?
H22E C22A H22F . . 109.5 ?
C32 C31 C39 . . 117.94(10) ?
C32 C31 C1 . . 120.25(9) ?
C39 C31 C1 . . 121.81(10) ?
N3 C32 C31 . . 121.89(10) ?
N3 C32 C33 . . 119.91(10) ?
C31 C32 C33 . . 118.17(10) ?
C38 C33 C34 . . 118.85(10) ?
C38 C33 C32 . . 118.10(10) ?
C34 C33 C32 . . 123.04(10) ?
C35 C34 C33 . . 120.73(10) ?
C35 C34 H34 . . 119.6 ?
C33 C34 H34 . . 119.6 ?
C34 C35 C36 . . 120.26(11) ?
C34 C35 H35 . . 119.9 ?
C36 C35 H35 . . 119.9 ?
C37 C36 C35 . . 120.03(11) ?
C37 C36 H36 . . 120.0 ?
C35 C36 H36 . . 120.0 ?
C36 C37 C38 . . 120.88(11) ?
C36 C37 H37 . . 119.6 ?
C38 C37 H37 . . 119.6 ?
N2 C38 C33 . . 122.92(10) ?
N2 C38 C37 . . 117.80(10) ?
C33 C38 C37 . . 119.23(10) ?
N2 C39 C31 . . 124.14(10) ?
N2 C39 C40 . . 112.97(9) ?
C31 C39 C40 . . 122.76(10) ?
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 ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C11 N1 C1 C31 . . . . 177.52(9) ?
C11 N1 C1 C2 . . . . 2.61(16) ?
C1 N1 C11 C12 . . . . -84.25(13) ?
C1 N1 C11 C16 . . . . 99.87(13) ?
C16 C11 C12 C13 . . . . 0.88(16) ?
N1 C11 C12 C13 . . . . -174.84(10) ?
C16 C11 C12 C17 . . . . 179.96(10) ?
N1 C11 C12 C17 . . . . 4.24(16) ?
C11 C12 C13 C14 . . . . 0.36(18) ?
C17 C12 C13 C14 . . . . -178.74(11) ?
C12 C13 C14 C15 . . . . -1.2(2) ?
C13 C14 C15 C16 . . . . 0.8(2) ?
C14 C15 C16 C11 . . . . 0.41(19) ?
C14 C15 C16 C20 . . . . 179.87(12) ?
C12 C11 C16 C15 . . . . -1.25(17) ?
N1 C11 C16 C15 . . . . 174.54(10) ?
C12 C11 C16 C20 . . . . 179.28(11) ?
N1 C11 C16 C20 . . . . -4.92(16) ?
C13 C12 C17 C19 . . . . -41.70(15) ?
C11 C12 C17 C19 . . . . 139.24(11) ?
C13 C12 C17 C18 . . . . 83.09(13) ?
C11 C12 C17 C18 . . . . -95.97(13) ?
C15 C16 C20 C22 . . . . 24.5(2) ?
C11 C16 C20 C22 . . . . -156.0(2) ?
C15 C16 C20 C21A . . . . -61.7(5) ?
C11 C16 C20 C21A . . . . 117.7(5) ?
C15 C16 C20 C21 . . . . -101.61(19) ?
C11 C16 C20 C21 . . . . 77.83(19) ?
C15 C16 C20 C22A . . . . 53.8(4) ?
C11 C16 C20 C22A . . . . -126.7(4) ?
N1 C1 C31 C32 . . . . -31.33(15) ?
C2 C1 C31 C32 . . . . 143.60(11) ?
N1 C1 C31 C39 . . . . 149.49(10) ?
C2 C1 C31 C39 . . . . -35.58(15) ?
C39 C31 C32 N3 . . . . -174.45(10) ?
C1 C31 C32 N3 . . . . 6.34(16) ?
C39 C31 C32 C33 . . . . 7.59(15) ?
C1 C31 C32 C33 . . . . -171.62(9) ?
N3 C32 C33 C38 . . . . 176.95(10) ?
C31 C32 C33 C38 . . . . -5.05(15) ?
N3 C32 C33 C34 . . . . -1.85(16) ?
C31 C32 C33 C34 . . . . 176.15(10) ?
C38 C33 C34 C35 . . . . -1.19(16) ?
C32 C33 C34 C35 . . . . 177.60(10) ?
C33 C34 C35 C36 . . . . 0.00(17) ?
C34 C35 C36 C37 . . . . 1.22(18) ?
C35 C36 C37 C38 . . . . -1.22(18) ?
C39 N2 C38 C33 . . . . 2.56(15) ?
C39 N2 C38 C37 . . . . -179.84(10) ?
C34 C33 C38 N2 . . . . 178.75(10) ?
C32 C33 C38 N2 . . . . -0.10(16) ?
C34 C33 C38 C37 . . . . 1.18(16) ?
C32 C33 C38 C37 . . . . -177.67(10) ?
C36 C37 C38 N2 . . . . -177.68(10) ?
C36 C37 C38 C33 . . . . 0.01(17) ?
C38 N2 C39 C31 . . . . 0.29(16) ?
C38 N2 C39 C40 . . . . -175.68(9) ?
C32 C31 C39 N2 . . . . -5.45(16) ?
C1 C31 C39 N2 . . . . 173.75(10) ?
C32 C31 C39 C40 . . . . 170.12(10) ?
C1 C31 C39 C40 . . . . -10.68(16) ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N3 H3A N1 . 0.960(16) 1.891(16) 2.6663(14) 136.0(12) ?
N3 H3B N2 4_565 0.913(17) 2.107(17) 2.9795(13) 159.5(14) ?

####################################################################### 
# 
# 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_dan9306
_database_code_depnum_ccdc_archive 'CCDC 1913158'
loop_
_audit_author_name
_audit_author_address
'Constantin G. Daniliuc'
;Organisch Chemisches Institut WWU University of Muenster
Germany
;
_audit_update_record             
;
2019-04-30 deposited with the CCDC.	2019-06-27 downloaded from the CCDC.
;

_audit_creation_method           'APEX3 v2016.1-0'
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H24 N4 O2'
_chemical_formula_iupac          ?
_chemical_formula_weight         424.49

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
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                   25.7345(9)
_cell_length_b                   11.2523(4)
_cell_length_c                   18.8485(6)
_cell_angle_alpha                90
_cell_angle_beta                 124.671(2)
_cell_angle_gamma                90
_cell_volume                     4488.8(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    5485
_cell_measurement_theta_min      4.1777
_cell_measurement_theta_max      66.3889
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.050
_exptl_crystal_density_diffrn    1.256
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1792

_exptl_absorpt_coefficient_mu    0.651
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
Bruker AXS (2014). SADABS, Version 2014/5, Bruker AXS Inc., Madison, Wisconsin,
USA.
;
_exptl_absorpt_correction_T_min  0.83
_exptl_absorpt_correction_T_max  0.97

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              'fine-focus sealed tube'

_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'Kappa CCD APEXII'
_diffrn_measurement_method       'phi / omega scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            36664
_diffrn_reflns_av_R_equivalents  0.0678
_diffrn_reflns_av_unetI/netI     0.0330
_diffrn_reflns_theta_min         4.18
_diffrn_reflns_theta_max         66.75
_diffrn_reflns_theta_full        66.75
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22

_refine_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.
;

_reflns_number_total             3973
_reflns_number_gt                3141
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0552
_refine_ls_R_factor_gt           0.0427
_refine_ls_wR_factor_gt          0.1087
_refine_ls_wR_factor_ref         0.1163
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      1.059
_refine_ls_number_reflns         3973
_refine_ls_number_parameters     297
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0614P)²+1.6458P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.156
_refine_diff_density_min         -0.265
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'

_computing_data_collection       'APEX3 v2016.1-0 (Bruker AXS Inc., 2016)'
_computing_cell_refinement       'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_data_reduction        'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'APEX3 v2016.1-0 (Bruker AXS Inc., 2016)'
_computing_publication_material  'APEX3 v2016.1-0 (Bruker AXS Inc., 2016)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N N1 0.43820(6) 0.18458(12) 0.59220(8) 0.0271(3) Uani d . . . 1 . .
N N2 0.51388(7) 0.56487(12) 0.64185(10) 0.0356(3) Uani d . . . 1 . .
N N3 0.57627(6) 0.22968(12) 0.76469(8) 0.0271(3) Uani d . . . 1 . .
H H3 0.5690(10) 0.2151(19) 0.8041(14) 0.049(6) Uiso d . . . 1 . .
N N4 0.78280(6) -0.01726(12) 0.81227(8) 0.0315(3) Uani d . . . 1 . .
O O1 0.79930(6) -0.11031(11) 0.85501(7) 0.0374(3) Uani d . . . 1 . .
O O2 0.81092(6) 0.02264(12) 0.78195(8) 0.0411(3) Uani d . . . 1 . .
C C1 0.47697(7) 0.24063(15) 0.58307(10) 0.0284(3) Uani d . . . 1 . .
C C2 0.49629(9) 0.20503(17) 0.52435(12) 0.0413(4) Uani d . . . 1 . .
H H2A 0.5401 0.1768 0.559 0.062 Uiso calc U . R 1 . .
H H2B 0.4928 0.2737 0.4899 0.062 Uiso calc U . R 1 . .
H H2C 0.4686 0.1413 0.4859 0.062 Uiso calc U . R 1 . .
C C11 0.40839(8) 0.07698(15) 0.54640(10) 0.0291(3) Uani d . . . 1 . .
C C12 0.34505(8) 0.08126(16) 0.47577(10) 0.0351(4) Uani d . . . 1 . .
C C13 0.31382(9) -0.02558(18) 0.43880(11) 0.0415(4) Uani d . . . 1 . .
H H13 0.2711 -0.0243 0.3901 0.05 Uiso calc U . R 1 . .
C C14 0.34380(9) -0.13344(17) 0.47174(12) 0.0425(4) Uani d . . . 1 . .
H H14 0.3215 -0.2055 0.4466 0.051 Uiso calc U . R 1 . .
C C15 0.40634(9) -0.13644(16) 0.54139(12) 0.0379(4) Uani d . . . 1 . .
H H15 0.4268 -0.2109 0.5635 0.045 Uiso calc U . R 1 . .
C C16 0.43980(8) -0.03166(15) 0.57958(11) 0.0328(4) Uani d . . . 1 . .
C C17 0.31176(9) 0.19823(19) 0.44142(13) 0.0520(5) Uani d . . . 1 . .
H H17A 0.267 0.1842 0.3962 0.078 Uiso calc U . R 1 . .
H H17B 0.3311 0.2428 0.4173 0.078 Uiso calc U . R 1 . .
H H17C 0.3155 0.2441 0.4883 0.078 Uiso calc U . R 1 . .
C C18 0.50757(9) -0.03575(17) 0.65559(13) 0.0449(5) Uani d . . . 1 . .
H H18A 0.5177 -0.1158 0.6806 0.067 Uiso calc U . R 1 . .
H H18B 0.5142 0.0218 0.699 0.067 Uiso calc U . R 1 . .
H H18C 0.535 -0.016 0.6368 0.067 Uiso calc U . R 1 . .
C C21 0.50754(7) 0.35015(14) 0.63674(10) 0.0270(3) Uani d . . . 1 . .
C C22 0.55529(7) 0.34230(14) 0.72283(10) 0.0261(3) Uani d . . . 1 . .
C C23 0.58476(8) 0.44742(14) 0.77149(11) 0.0300(4) Uani d . . . 1 . .
C C24 0.63449(8) 0.44713(16) 0.85994(11) 0.0357(4) Uani d . . . 1 . .
H H24 0.6492 0.3739 0.8902 0.043 Uiso calc U . R 1 . .
C C25 0.66177(9) 0.55181(18) 0.90261(12) 0.0436(5) Uani d . . . 1 . .
H H25 0.6947 0.5508 0.9624 0.052 Uiso calc U . R 1 . .
C C26 0.64111(9) 0.66013(18) 0.85817(14) 0.0484(5) Uani d . . . 1 . .
H H26 0.6608 0.7321 0.8878 0.058 Uiso calc U . R 1 . .
C C27 0.59304(9) 0.66315(17) 0.77277(14) 0.0465(5) Uani d . . . 1 . .
H H27 0.5796 0.7373 0.7435 0.056 Uiso calc U . R 1 . .
C C28 0.56281(8) 0.55715(15) 0.72703(11) 0.0335(4) Uani d . . . 1 . .
C C29 0.48687(8) 0.46593(15) 0.59862(10) 0.0309(4) Uani d . . . 1 . .
C C30 0.43128(8) 0.47918(17) 0.50667(11) 0.0392(4) Uani d . . . 1 . .
H H30A 0.4202 0.5635 0.4938 0.059 Uiso calc U . R 1 . .
H H30B 0.3952 0.4352 0.498 0.059 Uiso calc U . R 1 . .
H H30C 0.4421 0.4475 0.4682 0.059 Uiso calc U . R 1 . .
C C31 0.62768(7) 0.17170(14) 0.77587(9) 0.0261(3) Uani d . . . 1 . .
C C32 0.65032(8) 0.06819(14) 0.82689(10) 0.0293(4) Uani d . . . 1 . .
H H32 0.6306 0.041 0.8539 0.035 Uiso calc U . R 1 . .
C C33 0.70042(7) 0.00592(15) 0.83816(10) 0.0295(4) Uani d . . . 1 . .
H H33 0.7152 -0.0642 0.8722 0.035 Uiso calc U . R 1 . .
C C34 0.72931(7) 0.04727(14) 0.79879(10) 0.0275(3) Uani d . . . 1 . .
C C35 0.70806(7) 0.14905(14) 0.74830(10) 0.0280(3) Uani d . . . 1 . .
H H35 0.7283 0.176 0.722 0.034 Uiso calc U . R 1 . .
C C36 0.65740(7) 0.21085(14) 0.73641(9) 0.0273(3) Uani d . . . 1 . .
H H36 0.6425 0.2802 0.7014 0.033 Uiso calc U . R 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N1 C1 . 1.272(2) ?
N1 C11 . 1.430(2) ?
N2 C29 . 1.320(2) ?
N2 C28 . 1.368(2) ?
N3 C31 . 1.380(2) ?
N3 C22 . 1.427(2) ?
N3 H3 . 0.88(2) ?
N4 O2 . 1.2338(19) ?
N4 O1 . 1.2395(18) ?
N4 C34 . 1.445(2) ?
C1 C21 . 1.502(2) ?
C1 C2 . 1.503(2) ?
C2 H2A . 0.98 ?
C2 H2B . 0.98 ?
C2 H2C . 0.98 ?
C11 C12 . 1.401(2) ?
C11 C16 . 1.401(2) ?
C12 C13 . 1.393(3) ?
C12 C17 . 1.501(3) ?
C13 C14 . 1.382(3) ?
C13 H13 . 0.95 ?
C14 C15 . 1.382(3) ?
C14 H14 . 0.95 ?
C15 C16 . 1.395(2) ?
C15 H15 . 0.95 ?
C16 C18 . 1.501(3) ?
C17 H17A . 0.98 ?
C17 H17B . 0.98 ?
C17 H17C . 0.98 ?
C18 H18A . 0.98 ?
C18 H18B . 0.98 ?
C18 H18C . 0.98 ?
C21 C22 . 1.372(2) ?
C21 C29 . 1.436(2) ?
C22 C23 . 1.423(2) ?
C23 C24 . 1.411(2) ?
C23 C28 . 1.417(2) ?
C24 C25 . 1.373(3) ?
C24 H24 . 0.95 ?
C25 C26 . 1.401(3) ?
C25 H25 . 0.95 ?
C26 C27 . 1.363(3) ?
C26 H26 . 0.95 ?
C27 C28 . 1.417(3) ?
C27 H27 . 0.95 ?
C29 C30 . 1.501(2) ?
C30 H30A . 0.98 ?
C30 H30B . 0.98 ?
C30 H30C . 0.98 ?
C31 C36 . 1.407(2) ?
C31 C32 . 1.408(2) ?
C32 C33 . 1.374(2) ?
C32 H32 . 0.95 ?
C33 C34 . 1.395(2) ?
C33 H33 . 0.95 ?
C34 C35 . 1.387(2) ?
C35 C36 . 1.379(2) ?
C35 H35 . 0.95 ?
C36 H36 . 0.95 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C1 N1 C11 . . 122.04(13) ?
C29 N2 C28 . . 118.75(14) ?
C31 N3 C22 . . 122.19(13) ?
C31 N3 H3 . . 115.5(14) ?
C22 N3 H3 . . 115.9(14) ?
O2 N4 O1 . . 122.29(14) ?
O2 N4 C34 . . 119.12(13) ?
O1 N4 C34 . . 118.58(13) ?
N1 C1 C21 . . 117.79(13) ?
N1 C1 C2 . . 125.52(15) ?
C21 C1 C2 . . 116.67(14) ?
C1 C2 H2A . . 109.5 ?
C1 C2 H2B . . 109.5 ?
H2A C2 H2B . . 109.5 ?
C1 C2 H2C . . 109.5 ?
H2A C2 H2C . . 109.5 ?
H2B C2 H2C . . 109.5 ?
C12 C11 C16 . . 121.20(15) ?
C12 C11 N1 . . 118.62(15) ?
C16 C11 N1 . . 119.59(14) ?
C13 C12 C11 . . 118.30(17) ?
C13 C12 C17 . . 121.05(16) ?
C11 C12 C17 . . 120.65(16) ?
C14 C13 C12 . . 121.18(17) ?
C14 C13 H13 . . 119.4 ?
C12 C13 H13 . . 119.4 ?
C13 C14 C15 . . 119.94(17) ?
C13 C14 H14 . . 120.0 ?
C15 C14 H14 . . 120.0 ?
C14 C15 C16 . . 120.86(18) ?
C14 C15 H15 . . 119.6 ?
C16 C15 H15 . . 119.6 ?
C15 C16 C11 . . 118.50(16) ?
C15 C16 C18 . . 120.51(16) ?
C11 C16 C18 . . 120.98(15) ?
C12 C17 H17A . . 109.5 ?
C12 C17 H17B . . 109.5 ?
H17A C17 H17B . . 109.5 ?
C12 C17 H17C . . 109.5 ?
H17A C17 H17C . . 109.5 ?
H17B C17 H17C . . 109.5 ?
C16 C18 H18A . . 109.5 ?
C16 C18 H18B . . 109.5 ?
H18A C18 H18B . . 109.5 ?
C16 C18 H18C . . 109.5 ?
H18A C18 H18C . . 109.5 ?
H18B C18 H18C . . 109.5 ?
C22 C21 C29 . . 118.55(14) ?
C22 C21 C1 . . 121.16(14) ?
C29 C21 C1 . . 120.29(14) ?
C21 C22 C23 . . 119.95(14) ?
C21 C22 N3 . . 120.92(14) ?
C23 C22 N3 . . 119.13(14) ?
C24 C23 C28 . . 119.31(16) ?
C24 C23 C22 . . 123.53(15) ?
C28 C23 C22 . . 117.15(15) ?
C25 C24 C23 . . 120.54(17) ?
C25 C24 H24 . . 119.7 ?
C23 C24 H24 . . 119.7 ?
C24 C25 C26 . . 120.16(17) ?
C24 C25 H25 . . 119.9 ?
C26 C25 H25 . . 119.9 ?
C27 C26 C25 . . 120.57(18) ?
C27 C26 H26 . . 119.7 ?
C25 C26 H26 . . 119.7 ?
C26 C27 C28 . . 120.87(18) ?
C26 C27 H27 . . 119.6 ?
C28 C27 H27 . . 119.6 ?
N2 C28 C23 . . 122.74(15) ?
N2 C28 C27 . . 118.75(16) ?
C23 C28 C27 . . 118.52(17) ?
N2 C29 C21 . . 122.77(15) ?
N2 C29 C30 . . 116.77(15) ?
C21 C29 C30 . . 120.44(15) ?
C29 C30 H30A . . 109.5 ?
C29 C30 H30B . . 109.5 ?
H30A C30 H30B . . 109.5 ?
C29 C30 H30C . . 109.5 ?
H30A C30 H30C . . 109.5 ?
H30B C30 H30C . . 109.5 ?
N3 C31 C36 . . 122.26(14) ?
N3 C31 C32 . . 118.92(14) ?
C36 C31 C32 . . 118.80(14) ?
C33 C32 C31 . . 120.98(15) ?
C33 C32 H32 . . 119.5 ?
C31 C32 H32 . . 119.5 ?
C32 C33 C34 . . 119.00(15) ?
C32 C33 H33 . . 120.5 ?
C34 C33 H33 . . 120.5 ?
C35 C34 C33 . . 121.25(15) ?
C35 C34 N4 . . 119.98(14) ?
C33 C34 N4 . . 118.77(14) ?
C36 C35 C34 . . 119.68(14) ?
C36 C35 H35 . . 120.2 ?
C34 C35 H35 . . 120.2 ?
C35 C36 C31 . . 120.28(14) ?
C35 C36 H36 . . 119.9 ?
C31 C36 H36 . . 119.9 ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C11 N1 C1 C21 . . . . -177.69(13) ?
C11 N1 C1 C2 . . . . 0.7(2) ?
C1 N1 C11 C12 . . . . -103.88(18) ?
C1 N1 C11 C16 . . . . 84.80(19) ?
C16 C11 C12 C13 . . . . -0.2(2) ?
N1 C11 C12 C13 . . . . -171.41(15) ?
C16 C11 C12 C17 . . . . 179.38(17) ?
N1 C11 C12 C17 . . . . 8.2(2) ?
C11 C12 C13 C14 . . . . 1.4(3) ?
C17 C12 C13 C14 . . . . -178.21(18) ?
C12 C13 C14 C15 . . . . -1.5(3) ?
C13 C14 C15 C16 . . . . 0.4(3) ?
C14 C15 C16 C11 . . . . 0.7(2) ?
C14 C15 C16 C18 . . . . 179.56(17) ?
C12 C11 C16 C15 . . . . -0.8(2) ?
N1 C11 C16 C15 . . . . 170.28(14) ?
C12 C11 C16 C18 . . . . -179.64(16) ?
N1 C11 C16 C18 . . . . -8.5(2) ?
N1 C1 C21 C22 . . . . 75.5(2) ?
C2 C1 C21 C22 . . . . -103.05(18) ?
N1 C1 C21 C29 . . . . -104.13(17) ?
C2 C1 C21 C29 . . . . 77.31(19) ?
C29 C21 C22 C23 . . . . -2.4(2) ?
C1 C21 C22 C23 . . . . 178.00(13) ?
C29 C21 C22 N3 . . . . 177.91(13) ?
C1 C21 C22 N3 . . . . -1.7(2) ?
C31 N3 C22 C21 . . . . 95.78(18) ?
C31 N3 C22 C23 . . . . -83.95(18) ?
C21 C22 C23 C24 . . . . -179.40(15) ?
N3 C22 C23 C24 . . . . 0.3(2) ?
C21 C22 C23 C28 . . . . -0.4(2) ?
N3 C22 C23 C28 . . . . 179.38(13) ?
C28 C23 C24 C25 . . . . -0.5(3) ?
C22 C23 C24 C25 . . . . 178.56(16) ?
C23 C24 C25 C26 . . . . -1.1(3) ?
C24 C25 C26 C27 . . . . 1.3(3) ?
C25 C26 C27 C28 . . . . 0.1(3) ?
C29 N2 C28 C23 . . . . -1.6(2) ?
C29 N2 C28 C27 . . . . 178.15(16) ?
C24 C23 C28 N2 . . . . -178.44(15) ?
C22 C23 C28 N2 . . . . 2.5(2) ?
C24 C23 C28 C27 . . . . 1.8(2) ?
C22 C23 C28 C27 . . . . -177.29(15) ?
C26 C27 C28 N2 . . . . 178.59(17) ?
C26 C27 C28 C23 . . . . -1.6(3) ?
C28 N2 C29 C21 . . . . -1.4(2) ?
C28 N2 C29 C30 . . . . 176.94(15) ?
C22 C21 C29 N2 . . . . 3.4(2) ?
C1 C21 C29 N2 . . . . -176.98(15) ?
C22 C21 C29 C30 . . . . -174.87(14) ?
C1 C21 C29 C30 . . . . 4.8(2) ?
C22 N3 C31 C36 . . . . -9.2(2) ?
C22 N3 C31 C32 . . . . 172.30(14) ?
N3 C31 C32 C33 . . . . 178.44(14) ?
C36 C31 C32 C33 . . . . -0.1(2) ?
C31 C32 C33 C34 . . . . 0.6(2) ?
C32 C33 C34 C35 . . . . -0.5(2) ?
C32 C33 C34 N4 . . . . 178.78(14) ?
O2 N4 C34 C35 . . . . 3.6(2) ?
O1 N4 C34 C35 . . . . -177.35(14) ?
O2 N4 C34 C33 . . . . -175.71(14) ?
O1 N4 C34 C33 . . . . 3.4(2) ?
C33 C34 C35 C36 . . . . -0.1(2) ?
N4 C34 C35 C36 . . . . -179.35(14) ?
C34 C35 C36 C31 . . . . 0.6(2) ?
N3 C31 C36 C35 . . . . -178.98(14) ?
C32 C31 C36 C35 . . . . -0.5(2) ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N3 H3 N1 2_656 0.88(2) 2.09(2) 2.9689(18) 174.(2) ?

####################################################################### 
# 
# 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_dan9460
_database_code_depnum_ccdc_archive 'CCDC 1913073'
loop_
_audit_author_name
_audit_author_address
'Constantin G. Daniliuc'
;Organisch Chemisches Institut WWU University of Muenster
Germany
;
_audit_update_record             
;
2019-04-30 deposited with the CCDC.	2019-06-27 downloaded from the CCDC.
;

_audit_creation_method           'APEX3 v2016.1-0'
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H29 Al N4 O2'
_chemical_formula_iupac          ?
_chemical_formula_weight         480.53

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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                   9.1200(2)
_cell_length_b                   26.0690(6)
_cell_length_c                   10.7107(2)
_cell_angle_alpha                90
_cell_angle_beta                 101.9210(10)
_cell_angle_gamma                90
_cell_volume                     2491.54(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9927
_cell_measurement_theta_min      3.3907
_cell_measurement_theta_max      66.6306
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.120
_exptl_crystal_density_diffrn    1.281
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1016

_exptl_absorpt_coefficient_mu    0.972
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
Bruker AXS (2014). SADABS, Version 2014/5, Bruker AXS Inc., Madison, Wisconsin,
USA.
;
_exptl_absorpt_correction_T_min  0.77
_exptl_absorpt_correction_T_max  0.89

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              'fine-focus sealed tube'

_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'Kappa CCD APEXII'
_diffrn_measurement_method       'phi / omega scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            33282
_diffrn_reflns_av_R_equivalents  0.0447
_diffrn_reflns_av_unetI/netI     0.0247
_diffrn_reflns_theta_min         4.55
_diffrn_reflns_theta_max         66.63
_diffrn_reflns_theta_full        66.63
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measured_fraction_theta_full 0.985
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12

_refine_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.
;

_reflns_number_total             4337
_reflns_number_gt                3766
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0418
_refine_ls_R_factor_gt           0.0353
_refine_ls_wR_factor_gt          0.0907
_refine_ls_wR_factor_ref         0.0940
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.056
_refine_ls_number_reflns         4337
_refine_ls_number_parameters     322
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0447P)²+1.2409P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.314
_refine_diff_density_min         -0.327
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'
Al Al 0.2130 0.2455 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       'APEX3 v2016.1-0 (Bruker AXS Inc., 2016)'
_computing_cell_refinement       'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_data_reduction        'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'APEX3 v2016.1-0 (Bruker AXS Inc., 2016)'
_computing_publication_material  'APEX3 v2016.1-0 (Bruker AXS Inc., 2016)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Al Al1 0.39143(5) 0.58501(2) 0.37567(4) 0.01608(13) Uani d . . . 1 . .
C C1 0.41487(17) 0.64260(6) 0.15130(14) 0.0148(3) Uani d . . . 1 . .
C C2 0.40103(18) 0.68885(6) 0.06572(15) 0.0186(3) Uani d . . . 1 . .
H H2A 0.307 0.6869 0.0021 0.028 Uiso calc U . R 1 . .
H H2B 0.4857 0.6898 0.0223 0.028 Uiso calc U . R 1 . .
H H2C 0.4014 0.72 0.1169 0.028 Uiso calc U . R 1 . .
C C3 0.3226(2) 0.51753(6) 0.31082(17) 0.0259(4) Uani d . . . 1 . .
H H3A 0.3569 0.5108 0.2314 0.039 Uiso calc U . R 1 . .
H H3B 0.2129 0.5164 0.2942 0.039 Uiso calc U . R 1 . .
H H3C 0.3635 0.4914 0.3742 0.039 Uiso calc U . R 1 . .
C C4 0.32372(19) 0.60650(7) 0.52969(15) 0.0225(4) Uani d . . . 1 . .
H H4A 0.3589 0.5818 0.5984 0.034 Uiso calc U . R 1 . .
H H4B 0.214 0.6079 0.5119 0.034 Uiso calc U . R 1 . .
H H4C 0.3644 0.6405 0.5559 0.034 Uiso calc U . R 1 . .
C C11 0.23509(18) 0.67940(6) 0.25509(14) 0.0161(3) Uani d . . . 1 . .
C C12 0.28805(19) 0.72214(6) 0.33060(15) 0.0191(3) Uani d . . . 1 . .
C C13 0.1847(2) 0.76065(6) 0.33980(16) 0.0245(4) Uani d . . . 1 . .
H H13 0.2167 0.7902 0.39 0.029 Uiso calc U . R 1 . .
C C14 0.0362(2) 0.75669(6) 0.27722(16) 0.0261(4) Uani d . . . 1 . .
H H14 -0.032 0.7836 0.2835 0.031 Uiso calc U . R 1 . .
C C15 -0.01282(19) 0.71360(6) 0.20570(15) 0.0222(4) Uani d . . . 1 . .
H H15 -0.115 0.7111 0.1637 0.027 Uiso calc U . R 1 . .
C C16 0.08521(18) 0.67365(6) 0.19413(14) 0.0184(3) Uani d . . . 1 . .
C C17 0.4498(2) 0.72635(6) 0.39732(16) 0.0243(4) Uani d . . . 1 . .
H H17A 0.4731 0.6995 0.4624 0.036 Uiso calc U . R 1 . .
H H17B 0.4676 0.7601 0.438 0.036 Uiso calc U . R 1 . .
H H17C 0.5139 0.7222 0.335 0.036 Uiso calc U . R 1 . .
C C18 0.03091(19) 0.62586(6) 0.11949(16) 0.0231(4) Uani d . . . 1 . .
H H18A -0.0753 0.6297 0.0796 0.035 Uiso calc U . R 1 . .
H H18B 0.0437 0.5963 0.1771 0.035 Uiso calc U . R 1 . .
H H18C 0.0891 0.6205 0.0532 0.035 Uiso calc U . R 1 . .
C C21 0.52378(17) 0.60169(6) 0.13843(14) 0.0152(3) Uani d . . . 1 . .
C C22 0.61701(17) 0.58091(6) 0.24688(14) 0.0155(3) Uani d . . . 1 . .
C C23 0.72624(17) 0.54358(6) 0.22956(15) 0.0164(3) Uani d . . . 1 . .
C C24 0.81798(17) 0.51666(6) 0.33156(15) 0.0191(3) Uani d . . . 1 . .
H H24 0.8087 0.5233 0.4168 0.023 Uiso calc U . R 1 . .
C C25 0.91984(18) 0.48120(6) 0.30854(16) 0.0221(4) Uani d . . . 1 . .
H H25 0.9804 0.4633 0.3778 0.027 Uiso calc U . R 1 . .
C C26 0.93556(18) 0.47099(6) 0.18251(16) 0.0228(4) Uani d . . . 1 . .
H H26 1.0091 0.4473 0.1675 0.027 Uiso calc U . R 1 . .
C C27 0.84519(18) 0.49516(6) 0.08209(16) 0.0211(4) Uani d . . . 1 . .
H H27 0.8551 0.4877 -0.0026 0.025 Uiso calc U . R 1 . .
C C28 0.73688(17) 0.53128(6) 0.10311(15) 0.0173(3) Uani d . . . 1 . .
C C29 0.53866(17) 0.58387(6) 0.01431(14) 0.0167(3) Uani d . . . 1 . .
C C30 0.43206(19) 0.59908(6) -0.10720(15) 0.0218(4) Uani d . . . 1 . .
H H30A 0.4719 0.6291 -0.1444 0.033 Uiso calc U . R 1 . .
H H30B 0.3342 0.6076 -0.0883 0.033 Uiso calc U . R 1 . .
H H30C 0.4208 0.5705 -0.1679 0.033 Uiso calc U . R 1 . .
C C31 0.71418(17) 0.61518(6) 0.45647(14) 0.0156(3) Uani d . . . 1 . .
C C32 0.71385(18) 0.61461(6) 0.58807(14) 0.0179(3) Uani d . . . 1 . .
H H32 0.6317 0.5998 0.6169 0.021 Uiso calc U . R 1 . .
C C33 0.83105(18) 0.63524(6) 0.67504(15) 0.0197(3) Uani d . . . 1 . .
H H33 0.8315 0.6336 0.7637 0.024 Uiso calc U . R 1 . .
C C34 0.94898(18) 0.65851(6) 0.63272(15) 0.0202(3) Uani d . . . 1 . .
C C35 0.94926(18) 0.66215(6) 0.50331(16) 0.0207(3) Uani d . . . 1 . .
H H35 1.028 0.6796 0.4751 0.025 Uiso calc U . R 1 . .
C C36 0.83370(18) 0.64015(6) 0.41652(15) 0.0190(3) Uani d . . . 1 . .
H H36 0.8346 0.6418 0.3281 0.023 Uiso calc U . R 1 . .
N N1 0.33945(14) 0.63878(5) 0.24114(12) 0.0149(3) Uani d . . . 1 . .
N N2 0.64256(15) 0.55109(5) -0.00199(12) 0.0188(3) Uani d . . . 1 . .
N N3 0.59680(14) 0.59308(5) 0.37029(12) 0.0157(3) Uani d . . . 1 . .
N N4 1.07529(16) 0.67814(5) 0.72485(14) 0.0257(3) Uani d . . . 1 . .
O O1 1.08841(15) 0.66490(5) 0.83763(12) 0.0332(3) Uani d . . . 1 . .
O O2 1.16484(14) 0.70708(5) 0.68846(13) 0.0351(3) Uani d . . . 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Al1 N3 . 1.8974(13) ?
Al1 C3 . 1.9468(17) ?
Al1 C4 . 1.9591(16) ?
Al1 N1 . 1.9959(13) ?
C1 N1 . 1.297(2) ?
C1 C21 . 1.483(2) ?
C1 C2 . 1.504(2) ?
C2 H2A . 0.98 ?
C2 H2B . 0.98 ?
C2 H2C . 0.98 ?
C3 H3A . 0.98 ?
C3 H3B . 0.98 ?
C3 H3C . 0.98 ?
C4 H4A . 0.98 ?
C4 H4B . 0.98 ?
C4 H4C . 0.98 ?
C11 C16 . 1.396(2) ?
C11 C12 . 1.403(2) ?
C11 N1 . 1.4520(19) ?
C12 C13 . 1.394(2) ?
C12 C17 . 1.504(2) ?
C13 C14 . 1.385(3) ?
C13 H13 . 0.95 ?
C14 C15 . 1.381(2) ?
C14 H14 . 0.95 ?
C15 C16 . 1.395(2) ?
C15 H15 . 0.95 ?
C16 C18 . 1.507(2) ?
C17 H17A . 0.98 ?
C17 H17B . 0.98 ?
C17 H17C . 0.98 ?
C18 H18A . 0.98 ?
C18 H18B . 0.98 ?
C18 H18C . 0.98 ?
C21 C22 . 1.399(2) ?
C21 C29 . 1.441(2) ?
C22 N3 . 1.4080(19) ?
C22 C23 . 1.432(2) ?
C23 C28 . 1.414(2) ?
C23 C24 . 1.417(2) ?
C24 C25 . 1.368(2) ?
C24 H24 . 0.95 ?
C25 C26 . 1.412(2) ?
C25 H25 . 0.95 ?
C26 C27 . 1.366(2) ?
C26 H26 . 0.95 ?
C27 C28 . 1.416(2) ?
C27 H27 . 0.95 ?
C28 N2 . 1.369(2) ?
C29 N2 . 1.314(2) ?
C29 C30 . 1.508(2) ?
C30 H30A . 0.98 ?
C30 H30B . 0.98 ?
C30 H30C . 0.98 ?
C31 N3 . 1.386(2) ?
C31 C36 . 1.410(2) ?
C31 C32 . 1.410(2) ?
C32 C33 . 1.374(2) ?
C32 H32 . 0.95 ?
C33 C34 . 1.390(2) ?
C33 H33 . 0.95 ?
C34 C35 . 1.390(2) ?
C34 N4 . 1.447(2) ?
C35 C36 . 1.378(2) ?
C35 H35 . 0.95 ?
C36 H36 . 0.95 ?
N4 O2 . 1.233(2) ?
N4 O1 . 1.2381(19) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N3 Al1 C3 . . 109.68(7) ?
N3 Al1 C4 . . 118.60(7) ?
C3 Al1 C4 . . 115.12(8) ?
N3 Al1 N1 . . 89.36(6) ?
C3 Al1 N1 . . 111.47(7) ?
C4 Al1 N1 . . 109.75(6) ?
N1 C1 C21 . . 118.79(13) ?
N1 C1 C2 . . 121.54(14) ?
C21 C1 C2 . . 119.56(13) ?
C1 C2 H2A . . 109.5 ?
C1 C2 H2B . . 109.5 ?
H2A C2 H2B . . 109.5 ?
C1 C2 H2C . . 109.5 ?
H2A C2 H2C . . 109.5 ?
H2B C2 H2C . . 109.5 ?
Al1 C3 H3A . . 109.5 ?
Al1 C3 H3B . . 109.5 ?
H3A C3 H3B . . 109.5 ?
Al1 C3 H3C . . 109.5 ?
H3A C3 H3C . . 109.5 ?
H3B C3 H3C . . 109.5 ?
Al1 C4 H4A . . 109.5 ?
Al1 C4 H4B . . 109.5 ?
H4A C4 H4B . . 109.5 ?
Al1 C4 H4C . . 109.5 ?
H4A C4 H4C . . 109.5 ?
H4B C4 H4C . . 109.5 ?
C16 C11 C12 . . 122.84(14) ?
C16 C11 N1 . . 118.22(13) ?
C12 C11 N1 . . 118.93(14) ?
C13 C12 C11 . . 117.09(15) ?
C13 C12 C17 . . 121.65(15) ?
C11 C12 C17 . . 121.26(14) ?
C14 C13 C12 . . 121.32(16) ?
C14 C13 H13 . . 119.3 ?
C12 C13 H13 . . 119.3 ?
C15 C14 C13 . . 120.07(16) ?
C15 C14 H14 . . 120.0 ?
C13 C14 H14 . . 120.0 ?
C14 C15 C16 . . 121.12(16) ?
C14 C15 H15 . . 119.4 ?
C16 C15 H15 . . 119.4 ?
C15 C16 C11 . . 117.51(15) ?
C15 C16 C18 . . 121.19(15) ?
C11 C16 C18 . . 121.29(14) ?
C12 C17 H17A . . 109.5 ?
C12 C17 H17B . . 109.5 ?
H17A C17 H17B . . 109.5 ?
C12 C17 H17C . . 109.5 ?
H17A C17 H17C . . 109.5 ?
H17B C17 H17C . . 109.5 ?
C16 C18 H18A . . 109.5 ?
C16 C18 H18B . . 109.5 ?
H18A C18 H18B . . 109.5 ?
C16 C18 H18C . . 109.5 ?
H18A C18 H18C . . 109.5 ?
H18B C18 H18C . . 109.5 ?
C22 C21 C29 . . 118.96(14) ?
C22 C21 C1 . . 120.34(13) ?
C29 C21 C1 . . 120.67(13) ?
C21 C22 N3 . . 121.14(14) ?
C21 C22 C23 . . 118.38(14) ?
N3 C22 C23 . . 120.29(13) ?
C28 C23 C24 . . 118.66(14) ?
C28 C23 C22 . . 117.73(14) ?
C24 C23 C22 . . 123.53(14) ?
C25 C24 C23 . . 120.68(15) ?
C25 C24 H24 . . 119.7 ?
C23 C24 H24 . . 119.7 ?
C24 C25 C26 . . 120.42(15) ?
C24 C25 H25 . . 119.8 ?
C26 C25 H25 . . 119.8 ?
C27 C26 C25 . . 120.12(15) ?
C27 C26 H26 . . 119.9 ?
C25 C26 H26 . . 119.9 ?
C26 C27 C28 . . 120.57(15) ?
C26 C27 H27 . . 119.7 ?
C28 C27 H27 . . 119.7 ?
N2 C28 C23 . . 123.10(14) ?
N2 C28 C27 . . 117.43(14) ?
C23 C28 C27 . . 119.41(15) ?
N2 C29 C21 . . 122.69(14) ?
N2 C29 C30 . . 114.23(13) ?
C21 C29 C30 . . 123.01(14) ?
C29 C30 H30A . . 109.5 ?
C29 C30 H30B . . 109.5 ?
H30A C30 H30B . . 109.5 ?
C29 C30 H30C . . 109.5 ?
H30A C30 H30C . . 109.5 ?
H30B C30 H30C . . 109.5 ?
N3 C31 C36 . . 121.93(14) ?
N3 C31 C32 . . 120.02(14) ?
C36 C31 C32 . . 118.02(14) ?
C33 C32 C31 . . 120.76(15) ?
C33 C32 H32 . . 119.6 ?
C31 C32 H32 . . 119.6 ?
C32 C33 C34 . . 119.72(15) ?
C32 C33 H33 . . 120.1 ?
C34 C33 H33 . . 120.1 ?
C33 C34 C35 . . 121.07(14) ?
C33 C34 N4 . . 119.52(15) ?
C35 C34 N4 . . 119.40(15) ?
C36 C35 C34 . . 119.05(15) ?
C36 C35 H35 . . 120.5 ?
C34 C35 H35 . . 120.5 ?
C35 C36 C31 . . 121.26(15) ?
C35 C36 H36 . . 119.4 ?
C31 C36 H36 . . 119.4 ?
C1 N1 C11 . . 118.66(13) ?
C1 N1 Al1 . . 120.42(11) ?
C11 N1 Al1 . . 120.06(9) ?
C29 N2 C28 . . 118.94(13) ?
C31 N3 C22 . . 119.07(12) ?
C31 N3 Al1 . . 131.09(10) ?
C22 N3 Al1 . . 108.96(10) ?
O2 N4 O1 . . 122.84(14) ?
O2 N4 C34 . . 119.14(15) ?
O1 N4 C34 . . 118.02(15) ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C16 C11 C12 C13 . . . . -2.1(2) ?
N1 C11 C12 C13 . . . . 178.99(13) ?
C16 C11 C12 C17 . . . . 178.52(14) ?
N1 C11 C12 C17 . . . . -0.3(2) ?
C11 C12 C13 C14 . . . . 0.1(2) ?
C17 C12 C13 C14 . . . . 179.46(15) ?
C12 C13 C14 C15 . . . . 1.1(2) ?
C13 C14 C15 C16 . . . . -0.5(2) ?
C14 C15 C16 C11 . . . . -1.4(2) ?
C14 C15 C16 C18 . . . . 178.07(15) ?
C12 C11 C16 C15 . . . . 2.8(2) ?
N1 C11 C16 C15 . . . . -178.35(13) ?
C12 C11 C16 C18 . . . . -176.71(14) ?
N1 C11 C16 C18 . . . . 2.2(2) ?
N1 C1 C21 C22 . . . . -41.7(2) ?
C2 C1 C21 C22 . . . . 134.61(15) ?
N1 C1 C21 C29 . . . . 140.25(15) ?
C2 C1 C21 C29 . . . . -43.4(2) ?
C29 C21 C22 N3 . . . . -173.44(13) ?
C1 C21 C22 N3 . . . . 8.5(2) ?
C29 C21 C22 C23 . . . . 1.5(2) ?
C1 C21 C22 C23 . . . . -176.52(13) ?
C21 C22 C23 C28 . . . . 2.2(2) ?
N3 C22 C23 C28 . . . . 177.25(13) ?
C21 C22 C23 C24 . . . . -174.41(14) ?
N3 C22 C23 C24 . . . . 0.6(2) ?
C28 C23 C24 C25 . . . . 3.0(2) ?
C22 C23 C24 C25 . . . . 179.65(15) ?
C23 C24 C25 C26 . . . . 0.2(2) ?
C24 C25 C26 C27 . . . . -2.4(2) ?
C25 C26 C27 C28 . . . . 1.1(2) ?
C24 C23 C28 N2 . . . . 172.94(14) ?
C22 C23 C28 N2 . . . . -3.9(2) ?
C24 C23 C28 C27 . . . . -4.2(2) ?
C22 C23 C28 C27 . . . . 178.97(14) ?
C26 C27 C28 N2 . . . . -175.13(15) ?
C26 C27 C28 C23 . . . . 2.2(2) ?
C22 C21 C29 N2 . . . . -4.3(2) ?
C1 C21 C29 N2 . . . . 173.76(14) ?
C22 C21 C29 C30 . . . . 172.55(14) ?
C1 C21 C29 C30 . . . . -9.4(2) ?
N3 C31 C32 C33 . . . . 178.42(14) ?
C36 C31 C32 C33 . . . . -3.6(2) ?
C31 C32 C33 C34 . . . . 2.2(2) ?
C32 C33 C34 C35 . . . . 1.2(2) ?
C32 C33 C34 N4 . . . . -177.24(14) ?
C33 C34 C35 C36 . . . . -3.0(2) ?
N4 C34 C35 C36 . . . . 175.44(14) ?
C34 C35 C36 C31 . . . . 1.4(2) ?
N3 C31 C36 C35 . . . . 179.70(14) ?
C32 C31 C36 C35 . . . . 1.8(2) ?
C21 C1 N1 C11 . . . . 178.79(13) ?
C2 C1 N1 C11 . . . . 2.5(2) ?
C21 C1 N1 Al1 . . . . 9.43(18) ?
C2 C1 N1 Al1 . . . . -166.84(11) ?
C16 C11 N1 C1 . . . . 93.89(17) ?
C12 C11 N1 C1 . . . . -87.20(17) ?
C16 C11 N1 Al1 . . . . -96.70(14) ?
C12 C11 N1 Al1 . . . . 82.21(15) ?
C21 C29 N2 C28 . . . . 2.8(2) ?
C30 C29 N2 C28 . . . . -174.28(14) ?
C23 C28 N2 C29 . . . . 1.3(2) ?
C27 C28 N2 C29 . . . . 178.55(14) ?
C36 C31 N3 C22 . . . . 20.0(2) ?
C32 C31 N3 C22 . . . . -162.19(14) ?
C36 C31 N3 Al1 . . . . -148.05(13) ?
C32 C31 N3 Al1 . . . . 29.8(2) ?
C21 C22 N3 C31 . . . . -121.77(16) ?
C23 C22 N3 C31 . . . . 63.35(19) ?
C21 C22 N3 Al1 . . . . 48.69(16) ?
C23 C22 N3 Al1 . . . . -126.19(12) ?
C3 Al1 N3 C31 . . . . -139.47(14) ?
C4 Al1 N3 C31 . . . . -4.35(16) ?
N1 Al1 N3 C31 . . . . 107.90(14) ?
C3 Al1 N3 C22 . . . . 51.61(12) ?
C4 Al1 N3 C22 . . . . -173.28(10) ?
N1 Al1 N3 C22 . . . . -61.02(10) ?
C33 C34 N4 O2 . . . . -166.22(14) ?
C35 C34 N4 O2 . . . . 15.3(2) ?
C33 C34 N4 O1 . . . . 13.8(2) ?
C35 C34 N4 O1 . . . . -164.66(14) ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
C2 H2A O1 1_454 0.98 2.44 3.407(2) 168.8 ?

