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

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_a
_database_code_depnum_ccdc_archive 'CCDC 1852172'
_audit_update_record             
;
2018-06-28 deposited with the CCDC.	2020-03-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C32 H28 N3 O6'
_chemical_formula_weight         550.57

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P2(1)/n  '

loop_
_symmetry_equiv_pos_as_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                   11.010(3)
_cell_length_b                   17.603(5)
_cell_length_c                   15.172(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 109.260(5)
_cell_angle_gamma                90.00
_cell_volume                     2776.0(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1348
_cell_measurement_theta_min      2.32
_cell_measurement_theta_max      20.48

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.317
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1156
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.9764
_exptl_absorpt_correction_T_max  0.9818
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13880
_diffrn_reflns_av_R_equivalents  0.0645
_diffrn_reflns_av_sigmaI/netI    0.0790
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.83
_diffrn_reflns_theta_max         25.00
_reflns_number_total             4883
_reflns_number_gt                2587
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0500P)²+2.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0054(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4883
_refine_ls_number_parameters     371
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1315
_refine_ls_R_factor_gt           0.0692
_refine_ls_wR_factor_ref         0.1719
_refine_ls_wR_factor_gt          0.1494
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_restrained_S_all      1.021
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 1.0509(4) 0.0037(2) 0.6757(3) 0.0618(11) Uani 1 1 d . . .
C2 C 0.9581(5) 0.0123(3) 0.7146(3) 0.0745(13) Uani 1 1 d . . .
H2A H 0.9574 -0.0177 0.7649 0.089 Uiso 1 1 calc R . .
C3 C 0.8648(4) 0.0658(3) 0.6788(3) 0.0695(12) Uani 1 1 d . . .
H3A H 0.8013 0.0728 0.7060 0.083 Uiso 1 1 calc R . .
C4 C 0.8631(4) 0.1093(2) 0.6040(3) 0.0546(10) Uani 1 1 d . . .
C5 C 0.9571(4) 0.0983(2) 0.5654(3) 0.0649(11) Uani 1 1 d . . .
H5A H 0.9566 0.1270 0.5139 0.078 Uiso 1 1 calc R . .
C6 C 1.0528(4) 0.0455(2) 0.6011(3) 0.0674(11) Uani 1 1 d . . .
H6A H 1.1172 0.0386 0.5747 0.081 Uiso 1 1 calc R . .
C7 C 0.7655(4) 0.1705(2) 0.5671(3) 0.0691(12) Uani 1 1 d . . .
H7A H 0.7917 0.2010 0.5233 0.083 Uiso 1 1 calc R . .
H7B H 0.7655 0.2032 0.6185 0.083 Uiso 1 1 calc R . .
C8 C 0.6305(4) 0.1432(2) 0.5191(2) 0.0479(9) Uani 1 1 d . . .
C9 C 0.5828(3) 0.27659(19) 0.4704(2) 0.0487(9) Uani 1 1 d . . .
C10 C 0.5871(4) 0.3300(2) 0.5391(3) 0.0618(11) Uani 1 1 d . . .
C11 C 0.5489(5) 0.3116(3) 0.6229(3) 0.0961(17) Uani 1 1 d . . .
H11A H 0.5596 0.3558 0.6618 0.144 Uiso 1 1 calc R . .
H11B H 0.6022 0.2712 0.6577 0.144 Uiso 1 1 calc R . .
H11C H 0.4605 0.2959 0.6030 0.144 Uiso 1 1 calc R . .
C12 C 0.6255(5) 0.4025(2) 0.5260(3) 0.0784(13) Uani 1 1 d . . .
H12A H 0.6288 0.4397 0.5703 0.094 Uiso 1 1 calc R . .
C13 C 0.6584(4) 0.4208(2) 0.4502(4) 0.0780(13) Uani 1 1 d . . .
H13A H 0.6844 0.4701 0.4434 0.094 Uiso 1 1 calc R . .
C14 C 0.6538(4) 0.3674(2) 0.3834(3) 0.0675(12) Uani 1 1 d . . .
H14A H 0.6779 0.3806 0.3321 0.081 Uiso 1 1 calc R . .
C15 C 0.6139(4) 0.2942(2) 0.3916(3) 0.0534(10) Uani 1 1 d . . .
C16 C 0.6027(4) 0.2372(2) 0.3164(3) 0.0732(12) Uani 1 1 d . . .
H16A H 0.6299 0.2598 0.2684 0.110 Uiso 1 1 calc R . .
H16B H 0.5148 0.2210 0.2902 0.110 Uiso 1 1 calc R . .
H16C H 0.6562 0.1942 0.3422 0.110 Uiso 1 1 calc R . .
C17 C 0.4076(4) 0.18710(19) 0.4418(2) 0.0440(9) Uani 1 1 d . . .
C18 C 0.3426(3) 0.12167(18) 0.4766(2) 0.0421(8) Uani 1 1 d . . .
H18A H 0.3758 0.0733 0.4620 0.050 Uiso 1 1 calc R . .
C19 C 0.3665(3) 0.12534(18) 0.5790(2) 0.0405(8) Uani 1 1 d . . .
C20 C 0.2960(3) 0.18024(19) 0.6108(2) 0.0459(9) Uani 1 1 d . . .
C21 C 0.1886(3) 0.21665(18) 0.5382(2) 0.0420(8) Uani 1 1 d . . .
C22 C 0.1463(3) 0.18604(18) 0.4492(2) 0.0395(8) Uani 1 1 d . . .
C23 C 0.0346(3) 0.2114(2) 0.3835(2) 0.0485(9) Uani 1 1 d . . .
H23A H 0.0068 0.1905 0.3239 0.058 Uiso 1 1 calc R . .
C24 C -0.0354(4) 0.2678(2) 0.4070(2) 0.0567(10) Uani 1 1 d . . .
H24A H -0.1119 0.2844 0.3633 0.068 Uiso 1 1 calc R . .
C25 C 0.0068(4) 0.3002(2) 0.4949(3) 0.0587(10) Uani 1 1 d . . .
H25A H -0.0399 0.3392 0.5100 0.070 Uiso 1 1 calc R . .
C26 C 0.1176(4) 0.2745(2) 0.5592(2) 0.0528(10) Uani 1 1 d . . .
H26A H 0.1460 0.2962 0.6183 0.063 Uiso 1 1 calc R . .
C27 C 0.4452(3) 0.07457(19) 0.6397(2) 0.0493(9) Uani 1 1 d . . .
H27A H 0.4807 0.0358 0.6145 0.059 Uiso 1 1 calc R . .
C28 C 0.5591(4) 0.0257(3) 0.8005(3) 0.0666(11) Uani 1 1 d U . .
C29 C 0.4912(4) 0.0011(3) 0.8671(3) 0.0811(14) Uani 1 1 d . . .
H29A H 0.4659 0.0451 0.8941 0.122 Uiso 1 1 calc R . .
H29B H 0.5482 -0.0295 0.9157 0.122 Uiso 1 1 calc R . .
H29C H 0.4163 -0.0280 0.8340 0.122 Uiso 1 1 calc R . .
C30 C 0.6057(6) -0.0455(3) 0.7536(3) 0.118(2) Uani 1 1 d U . .
H30A H 0.6479 -0.0275 0.7114 0.177 Uiso 1 1 calc R . .
H30B H 0.5326 -0.0757 0.7198 0.177 Uiso 1 1 calc R . .
H30C H 0.6646 -0.0758 0.8014 0.177 Uiso 1 1 calc R . .
C31 C 0.6696(6) 0.0662(3) 0.8472(4) 0.0903(17) Uani 1 1 d . . .
C32 C 0.7553(9) 0.0999(4) 0.8810(5) 0.134(3) Uani 1 1 d . . .
N1 N 1.1546(4) -0.0516(2) 0.7149(4) 0.0925(14) Uani 1 1 d . . .
N2 N 0.5409(3) 0.20009(15) 0.48203(18) 0.0429(7) Uani 1 1 d . . .
N3 N 0.4742(3) 0.07653(18) 0.73093(19) 0.0657(10) Uani 1 1 d . . .
H3B H 0.4387 0.1123 0.7525 0.079 Uiso 1 1 calc R . .
O1 O 1.1613(4) -0.0808(2) 0.7891(3) 0.1297(16) Uani 1 1 d . . .
O2 O 1.2258(4) -0.0651(2) 0.6713(4) 0.1313(17) Uani 1 1 d . . .
O3 O 0.6005(2) 0.07714(13) 0.51317(17) 0.0553(7) Uani 1 1 d . . .
O4 O 0.3449(3) 0.23163(15) 0.38551(18) 0.0615(7) Uani 1 1 d . . .
O5 O 0.3146(3) 0.19402(15) 0.69472(15) 0.0644(8) Uani 1 1 d . . .
O6 O 0.2089(2) 0.12672(12) 0.42430(14) 0.0458(6) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.347(6) . ?
C1 C6 1.355(5) . ?
C1 N1 1.469(6) . ?
C2 C3 1.367(6) . ?
C2 H2A 0.9300 . ?
C3 C4 1.363(5) . ?
C3 H3A 0.9300 . ?
C4 C5 1.360(5) . ?
C4 C7 1.494(5) . ?
C5 C6 1.375(5) . ?
C5 H5A 0.9300 . ?
C6 H6A 0.9300 . ?
C7 C8 1.502(5) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 O3 1.203(4) . ?
C8 N2 1.388(4) . ?
C9 C15 1.383(5) . ?
C9 C10 1.392(5) . ?
C9 N2 1.453(4) . ?
C10 C12 1.380(5) . ?
C10 C11 1.501(5) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 C13 1.354(6) . ?
C12 H12A 0.9300 . ?
C13 C14 1.372(6) . ?
C13 H13A 0.9300 . ?
C14 C15 1.380(5) . ?
C14 H14A 0.9300 . ?
C15 C16 1.494(5) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 O4 1.196(4) . ?
C17 N2 1.410(4) . ?
C17 C18 1.539(5) . ?
C18 O6 1.426(4) . ?
C18 C19 1.490(4) . ?
C18 H18A 0.9800 . ?
C19 C27 1.367(4) . ?
C19 C20 1.419(4) . ?
C20 O5 1.245(3) . ?
C20 C21 1.471(5) . ?
C21 C26 1.383(5) . ?
C21 C22 1.385(4) . ?
C22 O6 1.371(4) . ?
C22 C23 1.376(5) . ?
C23 C24 1.375(5) . ?
C23 H23A 0.9300 . ?
C24 C25 1.382(5) . ?
C24 H24A 0.9300 . ?
C25 C26 1.364(5) . ?
C25 H25A 0.9300 . ?
C26 H26A 0.9300 . ?
C27 N3 1.315(4) . ?
C27 H27A 0.9300 . ?
C28 C31 1.387(7) . ?
C28 N3 1.462(5) . ?
C28 C29 1.505(5) . ?
C28 C30 1.607(7) . ?
C29 H29A 0.9600 . ?
C29 H29B 0.9600 . ?
C29 H29C 0.9600 . ?
C30 H30A 0.9600 . ?
C30 H30B 0.9600 . ?
C30 H30C 0.9600 . ?
C31 C32 1.088(8) . ?
N1 O2 1.205(6) . ?
N1 O1 1.218(5) . ?
N3 H3B 0.8600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 121.9(4) . . ?
C2 C1 N1 119.9(5) . . ?
C6 C1 N1 118.3(5) . . ?
C1 C2 C3 118.9(4) . . ?
C1 C2 H2A 120.6 . . ?
C3 C2 H2A 120.6 . . ?
C4 C3 C2 121.3(4) . . ?
C4 C3 H3A 119.4 . . ?
C2 C3 H3A 119.4 . . ?
C5 C4 C3 118.3(4) . . ?
C5 C4 C7 119.8(4) . . ?
C3 C4 C7 121.8(4) . . ?
C4 C5 C6 121.3(4) . . ?
C4 C5 H5A 119.3 . . ?
C6 C5 H5A 119.3 . . ?
C1 C6 C5 118.3(4) . . ?
C1 C6 H6A 120.8 . . ?
C5 C6 H6A 120.8 . . ?
C4 C7 C8 115.2(3) . . ?
C4 C7 H7A 108.5 . . ?
C8 C7 H7A 108.5 . . ?
C4 C7 H7B 108.5 . . ?
C8 C7 H7B 108.5 . . ?
H7A C7 H7B 107.5 . . ?
O3 C8 N2 121.8(3) . . ?
O3 C8 C7 123.2(3) . . ?
N2 C8 C7 115.0(3) . . ?
C15 C9 C10 122.6(3) . . ?
C15 C9 N2 119.4(3) . . ?
C10 C9 N2 117.9(3) . . ?
C12 C10 C9 117.0(4) . . ?
C12 C10 C11 120.4(4) . . ?
C9 C10 C11 122.6(3) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C13 C12 C10 121.5(4) . . ?
C13 C12 H12A 119.2 . . ?
C10 C12 H12A 119.2 . . ?
C12 C13 C14 120.6(4) . . ?
C12 C13 H13A 119.7 . . ?
C14 C13 H13A 119.7 . . ?
C13 C14 C15 120.6(4) . . ?
C13 C14 H14A 119.7 . . ?
C15 C14 H14A 119.7 . . ?
C14 C15 C9 117.7(4) . . ?
C14 C15 C16 120.4(3) . . ?
C9 C15 C16 121.9(3) . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O4 C17 N2 118.4(3) . . ?
O4 C17 C18 120.7(3) . . ?
N2 C17 C18 120.6(3) . . ?
O6 C18 C19 111.9(3) . . ?
O6 C18 C17 105.9(3) . . ?
C19 C18 C17 112.5(3) . . ?
O6 C18 H18A 108.8 . . ?
C19 C18 H18A 108.8 . . ?
C17 C18 H18A 108.8 . . ?
C27 C19 C20 120.8(3) . . ?
C27 C19 C18 121.9(3) . . ?
C20 C19 C18 117.1(3) . . ?
O5 C20 C19 123.8(3) . . ?
O5 C20 C21 120.0(3) . . ?
C19 C20 C21 115.9(3) . . ?
C26 C21 C22 118.5(3) . . ?
C26 C21 C20 121.6(3) . . ?
C22 C21 C20 119.3(3) . . ?
O6 C22 C23 117.3(3) . . ?
O6 C22 C21 121.8(3) . . ?
C23 C22 C21 120.8(3) . . ?
C24 C23 C22 119.4(3) . . ?
C24 C23 H23A 120.3 . . ?
C22 C23 H23A 120.3 . . ?
C23 C24 C25 120.6(4) . . ?
C23 C24 H24A 119.7 . . ?
C25 C24 H24A 119.7 . . ?
C26 C25 C24 119.3(3) . . ?
C26 C25 H25A 120.3 . . ?
C24 C25 H25A 120.3 . . ?
C25 C26 C21 121.3(3) . . ?
C25 C26 H26A 119.3 . . ?
C21 C26 H26A 119.3 . . ?
N3 C27 C19 124.9(3) . . ?
N3 C27 H27A 117.6 . . ?
C19 C27 H27A 117.6 . . ?
C31 C28 N3 107.4(4) . . ?
C31 C28 C29 110.5(4) . . ?
N3 C28 C29 108.7(4) . . ?
C31 C28 C30 105.8(4) . . ?
N3 C28 C30 112.3(3) . . ?
C29 C28 C30 112.0(4) . . ?
C28 C29 H29A 109.5 . . ?
C28 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C28 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C28 C30 H30A 109.5 . . ?
C28 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
C28 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C32 C31 C28 177.1(7) . . ?
O2 N1 O1 125.0(5) . . ?
O2 N1 C1 117.9(5) . . ?
O1 N1 C1 117.2(5) . . ?
C8 N2 C17 123.9(3) . . ?
C8 N2 C9 120.4(3) . . ?
C17 N2 C9 115.1(3) . . ?
C27 N3 C28 128.3(3) . . ?
C27 N3 H3B 115.8 . . ?
C28 N3 H3B 115.8 . . ?
C22 O6 C18 114.5(2) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         1.084
_refine_diff_density_min         -0.302
_refine_diff_density_rms         0.049
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
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data_a_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1962910'
_audit_update_record             
;
2019-10-31 deposited with the CCDC.	2020-03-06 downloaded from the CCDC.
;
_audit_creation_date             2019-01-13
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C23 H25 N5 O2'
_chemical_formula_sum            'C23 H25 N5 O2'
_chemical_formula_weight         403.48
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_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                   10.815(8)
_cell_length_b                   25.531(17)
_cell_length_c                   15.619(11)
_cell_angle_alpha                90
_cell_angle_beta                 90.186(14)
_cell_angle_gamma                90
_cell_volume                     4313(5)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    2363
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      19.98
_cell_measurement_theta_min      2.42
_shelx_estimated_absorpt_T_max   0.984
_shelx_estimated_absorpt_T_min   0.977
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  0.9837
_exptl_absorpt_correction_T_min  0.9774
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.243
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1712
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.2
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   0.984
_exptl_transmission_factor_min   0.977
_diffrn_reflns_av_R_equivalents  0.1501
_diffrn_reflns_av_unetI/netI     0.1485
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            21619
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         1.528
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3484
_reflns_number_total             7588
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v7.60A (Bruker, 2009)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v7.60A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_refine_diff_density_max         0.273
_refine_diff_density_min         -0.221
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     541
_refine_ls_number_reflns         7588
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.1552
_refine_ls_R_factor_gt           0.0767
_refine_ls_restrained_S_all      1.041
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0100P)²+0.1500P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1602
_refine_ls_wR_factor_ref         0.1816
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C19) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
3.a Ternary CH refined with riding coordinates:
 C10(H10), C32(H32)
3.b Me refined with riding coordinates:
 C1(H1A,H1B,H1C), C5(H5A,H5B,H5C), C20(H20A,H20B,H20C), C21(H21A,H21B,H21C),
 C22(H22A,H22B,H22C), C23(H23A,H23B,H23C), C27(H27A,H27B,H27C), C43(H43A,H43B,
 H43C), C44(H44A,H44B,H44C), C45(H45A,H45B,H45C)
3.c Aromatic/amide H refined with riding coordinates:
 N5(H5), N10(H10A), C6(H6), C7(H7), C8(H8), C15(H15), C16(H16), C17(H17),
 C18(H18), C28(H28), C29(H29), C30(H30), C36(H36), C37(H37), C38(H38), C39(H39),
  C41(H41), C65(H65)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.4344(3) 0.32240(10) -0.01036(19) 0.0558(8) Uani 1 1 d . . . . .
N2 N 0.3311(3) 0.30544(13) -0.0496(2) 0.0782(10) Uani 1 1 d . . . . .
N3 N 0.2821(3) 0.27134(14) 0.0006(3) 0.0870(11) Uani 1 1 d . . . . .
N4 N 0.3545(3) 0.26420(11) 0.0705(2) 0.0708(9) Uani 1 1 d . . . . .
N5 N 0.8181(3) 0.38663(13) 0.0874(2) 0.0763(10) Uani 1 1 d . . . . .
H5 H 0.7858 0.4171 0.0949 0.092 Uiso 1 1 calc R . . . .
N6 N -0.0622(3) 0.16483(11) 0.1696(2) 0.0591(8) Uani 1 1 d . . . . .
N7 N -0.1671(3) 0.18033(14) 0.2072(2) 0.0812(10) Uani 1 1 d . . . . .
N8 N -0.2177(3) 0.21408(14) 0.1585(3) 0.0868(11) Uani 1 1 d . . . . .
N9 N -0.1473(3) 0.22223(12) 0.0883(2) 0.0704(9) Uani 1 1 d . . . . .
N10 N 0.3185(3) 0.10055(11) 0.0702(2) 0.0695(10) Uani 1 1 d . . . . .
H10A H 0.2855 0.0705 0.0599 0.083 Uiso 1 1 calc R . . . .
O1 O 0.6223(2) 0.43776(10) 0.15599(16) 0.0716(8) Uani 1 1 d . . . . .
O2 O 0.4998(2) 0.29131(10) 0.20913(15) 0.0629(7) Uani 1 1 d . . . . .
O3 O 0.1231(2) 0.05322(9) -0.00653(15) 0.0665(7) Uani 1 1 d . . . . .
O4 O 0.0017(2) 0.20029(8) -0.04858(14) 0.0602(7) Uani 1 1 d . . . . .
C1 C 0.3481(4) 0.42742(15) -0.0006(2) 0.0738(12) Uani 1 1 d . . . . .
H1A H 0.3135 0.3967 0.0255 0.111 Uiso 1 1 calc R . . . .
H1B H 0.3685 0.4525 0.0430 0.111 Uiso 1 1 calc R . . . .
H1C H 0.2889 0.4424 -0.0394 0.111 Uiso 1 1 calc R . . . .
C2 C 0.4613(3) 0.41295(14) -0.0480(2) 0.0555(10) Uani 1 1 d . . . . .
C3 C 0.5047(3) 0.36212(14) -0.0522(2) 0.0528(9) Uani 1 1 d . . . . .
C4 C 0.6061(4) 0.34748(16) -0.0982(2) 0.0662(11) Uani 1 1 d . . . . .
C5 C 0.6449(4) 0.29146(14) -0.1066(3) 0.0900(14) Uani 1 1 d . . . . .
H5A H 0.7178 0.2894 -0.1413 0.135 Uiso 1 1 calc R . . . .
H5B H 0.6621 0.2773 -0.0509 0.135 Uiso 1 1 calc R . . . .
H5C H 0.5796 0.2717 -0.1331 0.135 Uiso 1 1 calc R . . . .
C6 C 0.6715(4) 0.38702(17) -0.1381(3) 0.0800(12) Uani 1 1 d . . . . .
H6 H 0.7434 0.3791 -0.1680 0.096 Uiso 1 1 calc R . . . .
C7 C 0.6315(5) 0.43747(18) -0.1339(3) 0.0816(13) Uani 1 1 d . . . . .
H7 H 0.6767 0.4635 -0.1612 0.098 Uiso 1 1 calc R . . . .
C8 C 0.5275(4) 0.45066(15) -0.0910(3) 0.0688(11) Uani 1 1 d . . . . .
H8 H 0.5008 0.4853 -0.0905 0.083 Uiso 1 1 calc R . . . .
C9 C 0.4475(3) 0.29634(12) 0.0631(2) 0.0505(9) Uani 1 1 d . . . . .
C10 C 0.5520(3) 0.29935(13) 0.1264(2) 0.0545(9) Uani 1 1 d . . . . .
H10 H 0.6076 0.2699 0.1148 0.065 Uiso 1 1 calc R . . . .
C11 C 0.6269(3) 0.34800(13) 0.1228(2) 0.0486(9) Uani 1 1 d . . . . .
C12 C 0.5752(3) 0.39367(15) 0.1612(2) 0.0543(10) Uani 1 1 d . . . . .
C13 C 0.4671(3) 0.38396(16) 0.2151(2) 0.0574(10) Uani 1 1 d . . . . .
C14 C 0.4363(4) 0.33382(17) 0.2385(2) 0.0608(10) Uani 1 1 d . . . . .
C15 C 0.3438(4) 0.3234(2) 0.2967(3) 0.0872(14) Uani 1 1 d . . . . .
H15 H 0.3267 0.2893 0.3139 0.105 Uiso 1 1 calc R . . . .
C16 C 0.2786(5) 0.3646(3) 0.3281(3) 0.1062(17) Uani 1 1 d . . . . .
H16 H 0.2134 0.3585 0.3654 0.127 Uiso 1 1 calc R . . . .
C17 C 0.3076(5) 0.4153(2) 0.3055(3) 0.1016(16) Uani 1 1 d . . . . .
H17 H 0.2630 0.4431 0.3284 0.122 Uiso 1 1 calc R . . . .
C18 C 0.4019(4) 0.42479(19) 0.2494(3) 0.0803(13) Uani 1 1 d . . . . .
H18 H 0.4217 0.4590 0.2345 0.096 Uiso 1 1 calc R . . . .
C19 C 0.9508(4) 0.38481(19) 0.0681(4) 0.0914(14) Uani 1 1 d . U . . .
C20 C 1.0176(5) 0.3633(3) 0.1438(4) 0.205(4) Uani 1 1 d . . . . .
H20A H 1.1045 0.3619 0.1319 0.307 Uiso 1 1 calc R . . . .
H20B H 1.0034 0.3854 0.1925 0.307 Uiso 1 1 calc R . . . .
H20C H 0.9878 0.3286 0.1558 0.307 Uiso 1 1 calc R . . . .
C21 C 0.9888(6) 0.4387(2) 0.0517(6) 0.234(5) Uani 1 1 d . . . . .
H21A H 1.0755 0.4395 0.0387 0.351 Uiso 1 1 calc R . . . .
H21B H 0.9427 0.4524 0.0040 0.351 Uiso 1 1 calc R . . . .
H21C H 0.9732 0.4597 0.1015 0.351 Uiso 1 1 calc R . . . .
C22 C 0.9745(5) 0.3503(2) -0.0077(4) 0.132(2) Uani 1 1 d . . . . .
H22A H 1.0615 0.3495 -0.0194 0.199 Uiso 1 1 calc R . . . .
H22B H 0.9460 0.3154 0.0045 0.199 Uiso 1 1 calc R . . . .
H22C H 0.9310 0.3638 -0.0566 0.199 Uiso 1 1 calc R . . . .
C23 C 0.1410(4) 0.20255(15) 0.2671(3) 0.0987(16) Uani 1 1 d . . . . .
H23A H 0.2134 0.2072 0.3020 0.148 Uiso 1 1 calc R . . . .
H23B H 0.1549 0.2175 0.2116 0.148 Uiso 1 1 calc R . . . .
H23C H 0.0720 0.2197 0.2936 0.148 Uiso 1 1 calc R . . . .
C24 C 0.1138(4) 0.14547(15) 0.2580(2) 0.0687(11) Uani 1 1 d . . . . .
C25 C 0.0150(3) 0.12713(14) 0.2113(2) 0.0581(10) Uani 1 1 d . . . . .
C26 C -0.0149(4) 0.07490(15) 0.2031(2) 0.0667(11) Uani 1 1 d . . . . .
C27 C -0.1251(4) 0.05631(14) 0.1537(3) 0.0822(13) Uani 1 1 d . . . . .
H27A H -0.1290 0.0188 0.1560 0.123 Uiso 1 1 calc R . . . .
H27B H -0.1988 0.0708 0.1783 0.123 Uiso 1 1 calc R . . . .
H27C H -0.1183 0.0674 0.0952 0.123 Uiso 1 1 calc R . . . .
C28 C 0.0630(5) 0.04058(15) 0.2433(3) 0.0869(14) Uani 1 1 d . . . . .
H28 H 0.0469 0.0049 0.2395 0.104 Uiso 1 1 calc R . . . .
C29 C 0.1638(5) 0.0570(2) 0.2889(3) 0.0993(16) Uani 1 1 d . . . . .
H29 H 0.2156 0.0325 0.3145 0.119 Uiso 1 1 calc R . . . .
C30 C 0.1886(5) 0.10855(19) 0.2969(3) 0.0929(15) Uani 1 1 d . . . . .
H30 H 0.2566 0.1193 0.3289 0.111 Uiso 1 1 calc R . . . .
C31 C -0.0512(3) 0.19144(13) 0.0959(2) 0.0517(9) Uani 1 1 d . . . . .
C32 C 0.0541(3) 0.18967(13) 0.0338(2) 0.0512(9) Uani 1 1 d . . . . .
H32 H 0.1098 0.2187 0.0479 0.061 Uiso 1 1 calc R . . . .
C33 C 0.1281(3) 0.14133(12) 0.0344(2) 0.0472(8) Uani 1 1 d . . . . .
C34 C 0.0744(3) 0.09720(14) -0.0062(2) 0.0510(9) Uani 1 1 d . . . . .
C35 C -0.0370(3) 0.10795(13) -0.0574(2) 0.0540(9) Uani 1 1 d . . . . .
C36 C -0.1098(4) 0.06764(15) -0.0900(2) 0.0746(12) Uani 1 1 d . . . . .
H36 H -0.0926 0.0331 -0.0754 0.089 Uiso 1 1 calc R . . . .
C37 C -0.2061(4) 0.0788(2) -0.1432(3) 0.0985(16) Uani 1 1 d . . . . .
H37 H -0.2551 0.0519 -0.1645 0.118 Uiso 1 1 calc R . . . .
C38 C -0.2309(5) 0.1294(2) -0.1653(3) 0.1029(17) Uani 1 1 d . . . . .
H38 H -0.2969 0.1365 -0.2017 0.123 Uiso 1 1 calc R . . . .
C39 C -0.1604(4) 0.16983(17) -0.1348(3) 0.0849(14) Uani 1 1 d . . . . .
H39 H -0.1765 0.2041 -0.1515 0.102 Uiso 1 1 calc R . . . .
C40 C -0.0651(3) 0.15869(14) -0.0789(2) 0.0594(10) Uani 1 1 d . . . . .
C41 C 0.2458(3) 0.14117(13) 0.0661(2) 0.0557(9) Uani 1 1 d . . . . .
H41 H 0.2768 0.1728 0.0865 0.067 Uiso 1 1 calc R . . . .
C42 C 0.4518(4) 0.10095(17) 0.0908(3) 0.0901(15) Uani 1 1 d . . . . .
C43 C 0.4791(5) 0.04595(18) 0.1235(5) 0.173(3) Uani 1 1 d . . . . .
H43A H 0.4294 0.0389 0.1730 0.260 Uiso 1 1 calc R . . . .
H43B H 0.4601 0.0209 0.0795 0.260 Uiso 1 1 calc R . . . .
H43C H 0.5650 0.0433 0.1386 0.260 Uiso 1 1 calc R . . . .
C44 C 0.5199(5) 0.1175(3) 0.0159(4) 0.185(4) Uani 1 1 d . . . . .
H44A H 0.6067 0.1178 0.0288 0.278 Uiso 1 1 calc R . . . .
H44B H 0.5043 0.0935 -0.0303 0.278 Uiso 1 1 calc R . . . .
H44C H 0.4938 0.1520 -0.0005 0.278 Uiso 1 1 calc R . . . .
C45 C 0.4770(4) 0.13836(19) 0.1647(3) 0.1179(19) Uani 1 1 d . . . . .
H45A H 0.4316 0.1272 0.2142 0.177 Uiso 1 1 calc R . . . .
H45B H 0.5639 0.1384 0.1777 0.177 Uiso 1 1 calc R . . . .
H45C H 0.4515 0.1731 0.1489 0.177 Uiso 1 1 calc R . . . .
C65 C 0.7452(3) 0.34670(15) 0.0941(2) 0.0591(10) Uani 1 1 d . . . . .
H65 H 0.7766 0.3143 0.0780 0.071 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 N2 1.344(4) . ?
N1 C3 1.427(4) . ?
N1 C9 1.334(4) . ?
N2 N3 1.288(4) . ?
N3 N4 1.354(4) . ?
N4 C9 1.303(4) . ?
N5 H5 0.8600 . ?
N5 C19 1.469(5) . ?
N5 C65 1.293(4) . ?
N6 N7 1.339(4) . ?
N6 C25 1.430(4) . ?
N6 C31 1.342(4) . ?
N7 N8 1.271(4) . ?
N8 N9 1.354(5) . ?
N9 C31 1.308(4) . ?
N10 H10A 0.8600 . ?
N10 C41 1.303(4) . ?
N10 C42 1.476(5) . ?
O1 C12 1.238(4) . ?
O2 C10 1.427(4) . ?
O2 C14 1.365(4) . ?
O3 C34 1.241(3) . ?
O4 C32 1.431(4) . ?
O4 C40 1.369(4) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C1 C2 1.481(5) . ?
C2 C3 1.382(5) . ?
C2 C8 1.375(5) . ?
C3 C4 1.365(5) . ?
C4 C5 1.496(5) . ?
C4 C6 1.383(5) . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C6 H6 0.9300 . ?
C6 C7 1.360(5) . ?
C7 H7 0.9300 . ?
C7 C8 1.354(6) . ?
C8 H8 0.9300 . ?
C9 C10 1.501(4) . ?
C10 H10 0.9800 . ?
C10 C11 1.484(4) . ?
C11 C12 1.426(5) . ?
C11 C65 1.357(5) . ?
C12 C13 1.464(6) . ?
C13 C14 1.373(5) . ?
C13 C18 1.369(5) . ?
C14 C15 1.379(6) . ?
C15 H15 0.9300 . ?
C15 C16 1.358(6) . ?
C16 H16 0.9300 . ?
C16 C17 1.376(6) . ?
C17 H17 0.9300 . ?
C17 C18 1.369(7) . ?
C18 H18 0.9300 . ?
C19 C20 1.488(7) . ?
C19 C21 1.460(6) . ?
C19 C22 1.499(6) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C23 C24 1.493(5) . ?
C24 C25 1.374(4) . ?
C24 C30 1.382(5) . ?
C25 C26 1.378(5) . ?
C26 C27 1.495(5) . ?
C26 C28 1.367(5) . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?
C28 H28 0.9300 . ?
C28 C29 1.365(6) . ?
C29 H29 0.9300 . ?
C29 C30 1.349(5) . ?
C30 H30 0.9300 . ?
C31 C32 1.499(5) . ?
C32 H32 0.9800 . ?
C32 C33 1.471(4) . ?
C33 C34 1.416(4) . ?
C33 C41 1.365(4) . ?
C34 C35 1.470(4) . ?
C35 C36 1.391(4) . ?
C35 C40 1.372(4) . ?
C36 H36 0.9300 . ?
C36 C37 1.360(5) . ?
C37 H37 0.9300 . ?
C37 C38 1.363(6) . ?
C38 H38 0.9300 . ?
C38 C39 1.368(5) . ?
C39 H39 0.9300 . ?
C39 C40 1.378(4) . ?
C41 H41 0.9300 . ?
C42 C43 1.523(6) . ?
C42 C44 1.447(7) . ?
C42 C45 1.523(6) . ?
C43 H43A 0.9600 . ?
C43 H43B 0.9600 . ?
C43 H43C 0.9600 . ?
C44 H44A 0.9600 . ?
C44 H44B 0.9600 . ?
C44 H44C 0.9600 . ?
C45 H45A 0.9600 . ?
C45 H45B 0.9600 . ?
C45 H45C 0.9600 . ?
C65 H65 0.9300 . ?

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
N2 N1 C3 117.6(3) . . ?
C9 N1 N2 108.6(3) . . ?
C9 N1 C3 133.9(3) . . ?
N3 N2 N1 106.4(3) . . ?
N2 N3 N4 110.1(3) . . ?
C9 N4 N3 106.7(3) . . ?
C19 N5 H5 117.0 . . ?
C65 N5 H5 117.0 . . ?
C65 N5 C19 126.0(4) . . ?
N7 N6 C25 119.5(3) . . ?
N7 N6 C31 107.7(3) . . ?
C31 N6 C25 132.7(3) . . ?
N8 N7 N6 107.5(4) . . ?
N7 N8 N9 110.4(3) . . ?
C31 N9 N8 106.4(3) . . ?
C41 N10 H10A 116.8 . . ?
C41 N10 C42 126.4(3) . . ?
C42 N10 H10A 116.8 . . ?
C14 O2 C10 113.0(3) . . ?
C40 O4 C32 111.8(2) . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
C3 C2 C1 122.6(4) . . ?
C8 C2 C1 120.1(4) . . ?
C8 C2 C3 117.2(4) . . ?
C2 C3 N1 117.7(4) . . ?
C4 C3 N1 118.5(3) . . ?
C4 C3 C2 123.7(4) . . ?
C3 C4 C5 122.3(4) . . ?
C3 C4 C6 116.8(4) . . ?
C6 C4 C5 121.0(4) . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C4 C6 H6 119.8 . . ?
C7 C6 C4 120.4(4) . . ?
C7 C6 H6 119.8 . . ?
C6 C7 H7 119.2 . . ?
C8 C7 C6 121.6(5) . . ?
C8 C7 H7 119.2 . . ?
C2 C8 H8 119.9 . . ?
C7 C8 C2 120.1(4) . . ?
C7 C8 H8 119.9 . . ?
N1 C9 C10 128.2(3) . . ?
N4 C9 N1 108.1(3) . . ?
N4 C9 C10 123.6(3) . . ?
O2 C10 C9 106.9(3) . . ?
O2 C10 H10 107.5 . . ?
O2 C10 C11 111.8(3) . . ?
C9 C10 H10 107.5 . . ?
C11 C10 C9 115.3(3) . . ?
C11 C10 H10 107.5 . . ?
C12 C11 C10 117.0(3) . . ?
C65 C11 C10 120.5(3) . . ?
C65 C11 C12 122.0(3) . . ?
O1 C12 C11 123.6(4) . . ?
O1 C12 C13 121.4(4) . . ?
C11 C12 C13 114.7(3) . . ?
C14 C13 C12 120.4(4) . . ?
C18 C13 C12 120.6(4) . . ?
C18 C13 C14 118.7(4) . . ?
O2 C14 C13 121.9(4) . . ?
O2 C14 C15 115.8(4) . . ?
C15 C14 C13 122.2(4) . . ?
C14 C15 H15 121.1 . . ?
C16 C15 C14 117.8(5) . . ?
C16 C15 H15 121.1 . . ?
C15 C16 H16 119.5 . . ?
C15 C16 C17 121.1(5) . . ?
C17 C16 H16 119.5 . . ?
C16 C17 H17 120.0 . . ?
C16 C17 C18 120.1(5) . . ?
C18 C17 H17 120.0 . . ?
C13 C18 C17 120.1(5) . . ?
C13 C18 H18 120.0 . . ?
C17 C18 H18 120.0 . . ?
N5 C19 C20 108.7(4) . . ?
N5 C19 C21 106.4(4) . . ?
N5 C19 C22 110.5(4) . . ?
C20 C19 C22 109.1(5) . . ?
C21 C19 C20 110.6(5) . . ?
C21 C19 C22 111.5(5) . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C19 C21 H21A 109.5 . . ?
C19 C21 H21B 109.5 . . ?
C19 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C19 C22 H22A 109.5 . . ?
C19 C22 H22B 109.5 . . ?
C19 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C24 C23 H23A 109.5 . . ?
C24 C23 H23B 109.5 . . ?
C24 C23 H23C 109.5 . . ?
C25 C24 C23 122.4(3) . . ?
C25 C24 C30 117.0(4) . . ?
C30 C24 C23 120.6(3) . . ?
C24 C25 N6 117.7(3) . . ?
C24 C25 C26 124.1(3) . . ?
C26 C25 N6 118.2(3) . . ?
C25 C26 C27 122.8(3) . . ?
C25 C26 C28 115.7(3) . . ?
C28 C26 C27 121.5(4) . . ?
C26 C27 H27A 109.5 . . ?
C26 C27 H27B 109.5 . . ?
C26 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C26 C28 H28 118.9 . . ?
C29 C28 C26 122.2(4) . . ?
C29 C28 H28 118.9 . . ?
C28 C29 H29 119.8 . . ?
C30 C29 C28 120.4(4) . . ?
C30 C29 H29 119.8 . . ?
C24 C30 H30 119.7 . . ?
C29 C30 C24 120.6(4) . . ?
C29 C30 H30 119.7 . . ?
N6 C31 C32 127.5(3) . . ?
N9 C31 N6 108.0(3) . . ?
N9 C31 C32 124.4(3) . . ?
O4 C32 C31 106.1(3) . . ?
O4 C32 H32 107.5 . . ?
O4 C32 C33 112.2(3) . . ?
C31 C32 H32 107.5 . . ?
C33 C32 C31 115.8(3) . . ?
C33 C32 H32 107.5 . . ?
C34 C33 C32 116.3(3) . . ?
C41 C33 C32 120.8(3) . . ?
C41 C33 C34 122.7(3) . . ?
O3 C34 C33 123.2(3) . . ?
O3 C34 C35 120.9(3) . . ?
C33 C34 C35 115.4(3) . . ?
C36 C35 C34 121.5(3) . . ?
C40 C35 C34 119.3(3) . . ?
C40 C35 C36 119.0(3) . . ?
C35 C36 H36 120.0 . . ?
C37 C36 C35 119.9(4) . . ?
C37 C36 H36 120.0 . . ?
C36 C37 H37 119.9 . . ?
C38 C37 C36 120.2(4) . . ?
C38 C37 H37 119.9 . . ?
C37 C38 H38 119.4 . . ?
C37 C38 C39 121.2(4) . . ?
C39 C38 H38 119.4 . . ?
C38 C39 H39 120.7 . . ?
C38 C39 C40 118.6(4) . . ?
C40 C39 H39 120.7 . . ?
O4 C40 C39 116.9(3) . . ?
C35 C40 O4 122.1(3) . . ?
C35 C40 C39 121.0(3) . . ?
N10 C41 C33 125.6(3) . . ?
N10 C41 H41 117.2 . . ?
C33 C41 H41 117.2 . . ?
N10 C42 C43 104.8(4) . . ?
N10 C42 C45 110.0(4) . . ?
C44 C42 N10 109.0(4) . . ?
C44 C42 C43 116.2(6) . . ?
C44 C42 C45 109.8(5) . . ?
C45 C42 C43 106.9(4) . . ?
C42 C43 H43A 109.5 . . ?
C42 C43 H43B 109.5 . . ?
C42 C43 H43C 109.5 . . ?
H43A C43 H43B 109.5 . . ?
H43A C43 H43C 109.5 . . ?
H43B C43 H43C 109.5 . . ?
C42 C44 H44A 109.5 . . ?
C42 C44 H44B 109.5 . . ?
C42 C44 H44C 109.5 . . ?
H44A C44 H44B 109.5 . . ?
H44A C44 H44C 109.5 . . ?
H44B C44 H44C 109.5 . . ?
C42 C45 H45A 109.5 . . ?
C42 C45 H45B 109.5 . . ?
C42 C45 H45C 109.5 . . ?
H45A C45 H45B 109.5 . . ?
H45A C45 H45C 109.5 . . ?
H45B C45 H45C 109.5 . . ?
N5 C65 C11 125.7(4) . . ?
N5 C65 H65 117.2 . . ?
C11 C65 H65 117.2 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
