# Electronic Supplementary Material (ESI) for Green Chemistry.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# 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_paran_11_0m
_database_code_depnum_ccdc_archive 'CCDC 1850625'
_audit_update_record             
;
2018-06-20 deposited with the CCDC.
2018-11-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C40 H36 N8 O4 S2'
_chemical_formula_weight         756.89

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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           ?
_symmetry_space_group_name_H-M   ?

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.651(5)
_cell_length_b                   12.816(5)
_cell_length_c                   14.137(5)
_cell_angle_alpha                100.211(5)
_cell_angle_beta                 107.686(5)
_cell_angle_gamma                101.151(5)
_cell_volume                     1745.4(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.440
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             792
_exptl_absorpt_coefficient_mu    0.210
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71069
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            34747
_diffrn_reflns_av_R_equivalents  0.0260
_diffrn_reflns_av_sigmaI/netI    0.0274
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.56
_diffrn_reflns_theta_max         29.12
_reflns_number_total             9335
_reflns_number_gt                7020
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.2000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         9335
_refine_ls_number_parameters     487
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1249
_refine_ls_R_factor_gt           0.1044
_refine_ls_wR_factor_ref         0.3836
_refine_ls_wR_factor_gt          0.3581
_refine_ls_goodness_of_fit_ref   1.604
_refine_ls_restrained_S_all      1.604
_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
S1 S 0.53080(12) 0.07144(11) 0.64347(9) 0.0654(4) Uani 1 1 d . . .
S2 S 0.03218(13) 0.51700(12) 0.13126(10) 0.0716(4) Uani 1 1 d . . .
C29 C 0.0009(2) 0.3605(2) 0.23447(16) 0.0176(4) Uani 1 1 d . . .
H29 H 0.0157 0.3146 0.2785 0.021 Uiso 1 1 calc R . .
N4 N 0.2414(3) 0.0255(2) 0.7747(2) 0.0348(6) Uani 1 1 d . . .
C9 C 0.5285(3) 0.1455(3) 0.8356(2) 0.0310(6) Uani 1 1 d . . .
H9 H 0.5019 0.1619 0.8922 0.037 Uiso 1 1 calc R . .
O3 O 0.3168(3) 0.4900(2) 0.09195(18) 0.0459(6) Uani 1 1 d . . .
N7 N 0.3726(3) 0.3353(2) 0.37917(19) 0.0312(5) Uani 1 1 d . . .
N6 N 0.4470(3) 0.2739(2) 0.2462(2) 0.0332(6) Uani 1 1 d . . .
O4 O 0.5310(3) 0.2173(2) 0.1221(2) 0.0506(7) Uani 1 1 d . . .
N5 N 0.4198(3) 0.3502(2) 0.1043(2) 0.0361(6) Uani 1 1 d . . .
N8 N 0.2870(3) 0.4915(2) 0.38521(18) 0.0308(5) Uani 1 1 d . . .
N3 N 0.1360(3) 0.1667(2) 0.7378(2) 0.0338(6) Uani 1 1 d . . .
C25 C 0.3308(3) 0.4144(2) 0.2335(2) 0.0294(6) Uani 1 1 d . . .
O1 O 0.2537(3) -0.0286(2) 0.4730(2) 0.0505(6) Uani 1 1 d . . .
C27 C 0.2579(3) 0.4889(2) 0.2760(2) 0.0291(6) Uani 1 1 d . . .
H27 H 0.2945 0.5632 0.2711 0.035 Uiso 1 1 calc R . .
C4 C 0.1398(3) 0.1404(2) 0.6416(2) 0.0308(6) Uani 1 1 d . . .
N2 N 0.0676(3) 0.1904(2) 0.5726(2) 0.0371(6) Uani 1 1 d . . .
N1 N 0.1337(3) 0.0991(3) 0.4433(2) 0.0416(7) Uani 1 1 d . . .
C24 C 0.3804(3) 0.3433(2) 0.2859(2) 0.0281(6) Uani 1 1 d . . .
C28 C 0.1052(3) 0.4560(3) 0.2199(2) 0.0322(6) Uani 1 1 d . . .
O2 O -0.0013(3) 0.2167(3) 0.4111(2) 0.0615(8) Uani 1 1 d . . .
C13 C 0.1515(3) 0.1170(3) 0.8953(2) 0.0334(6) Uani 1 1 d . . .
C26 C 0.3524(3) 0.4236(3) 0.1401(2) 0.0340(6) Uani 1 1 d . . .
C8 C 0.4418(3) 0.0749(3) 0.7246(2) 0.0355(7) Uani 1 1 d . . .
C32 C 0.3309(3) 0.4123(2) 0.4261(2) 0.0280(6) Uani 1 1 d . . .
C33 C 0.3356(3) 0.4139(2) 0.5323(2) 0.0323(6) Uani 1 1 d . . .
C7 C 0.2908(3) 0.0179(2) 0.6887(2) 0.0323(6) Uani 1 1 d . . .
H7 H 0.2769 -0.0598 0.6571 0.039 Uiso 1 1 calc R . .
C12 C 0.1785(3) 0.1033(2) 0.7978(2) 0.0307(6) Uani 1 1 d . . .
C5 C 0.2066(3) 0.0670(2) 0.6106(2) 0.0316(6) Uani 1 1 d . . .
C34 C 0.4011(4) 0.3469(3) 0.5854(3) 0.0408(7) Uani 1 1 d . . .
H34 H 0.4426 0.3012 0.5539 0.049 Uiso 1 1 calc R . .
C22 C 0.4710(3) 0.2767(3) 0.1552(2) 0.0358(7) Uani 1 1 d . . .
C38 C 0.2710(4) 0.4812(3) 0.5780(2) 0.0397(7) Uani 1 1 d . . .
C6 C 0.2020(3) 0.0398(3) 0.5072(2) 0.0351(6) Uani 1 1 d . . .
C14 C 0.0746(4) 0.1892(3) 0.9164(3) 0.0416(7) Uani 1 1 d . . .
H14 H 0.0380 0.2262 0.8682 0.050 Uiso 1 1 calc R . .
C18 C 0.2043(4) 0.0591(3) 0.9668(2) 0.0382(7) Uani 1 1 d . . .
C2 C 0.0644(4) 0.1717(3) 0.4729(3) 0.0423(8) Uani 1 1 d . . .
C20 C 0.2544(4) -0.0606(3) 0.8309(3) 0.0432(8) Uani 1 1 d . . .
H20A H 0.3244 -0.0942 0.8192 0.052 Uiso 1 1 calc R . .
H20B H 0.1687 -0.1172 0.8049 0.052 Uiso 1 1 calc R . .
C40 C 0.2628(4) 0.5852(3) 0.4471(3) 0.0431(8) Uani 1 1 d . . .
H40A H 0.2057 0.6200 0.4022 0.052 Uiso 1 1 calc R . .
H40B H 0.3491 0.6391 0.4870 0.052 Uiso 1 1 calc R . .
C21 C 0.4409(4) 0.3539(3) 0.0078(3) 0.0509(9) Uani 1 1 d . . .
H21A H 0.4007 0.4078 -0.0199 0.076 Uiso 1 1 calc R . .
H21B H 0.3988 0.2831 -0.0399 0.076 Uiso 1 1 calc R . .
H21C H 0.5370 0.3734 0.0196 0.076 Uiso 1 1 calc R . .
C39 C 0.1935(4) 0.5467(3) 0.5180(3) 0.0479(8) Uani 1 1 d . . .
H39A H 0.1879 0.6097 0.5644 0.057 Uiso 1 1 calc R . .
H39B H 0.1012 0.5021 0.4782 0.057 Uiso 1 1 calc R . .
C17 C 0.1792(4) 0.0757(3) 1.0592(3) 0.0487(9) Uani 1 1 d . . .
H17 H 0.2116 0.0369 1.1068 0.058 Uiso 1 1 calc R . .
C35 C 0.4055(4) 0.3471(3) 0.6836(3) 0.0520(10) Uani 1 1 d . . .
H35 H 0.4502 0.3022 0.7186 0.062 Uiso 1 1 calc R . .
C19 C 0.2915(4) -0.0140(3) 0.9452(3) 0.0482(9) Uani 1 1 d . . .
H19A H 0.2804 -0.0740 0.9779 0.058 Uiso 1 1 calc R . .
H19B H 0.3867 0.0275 0.9746 0.058 Uiso 1 1 calc R . .
C23 C 0.4992(5) 0.1947(3) 0.2990(3) 0.0521(9) Uani 1 1 d . . .
H23A H 0.5413 0.1541 0.2596 0.078 Uiso 1 1 calc R . .
H23B H 0.4251 0.1449 0.3066 0.078 Uiso 1 1 calc R . .
H23C H 0.5654 0.2329 0.3655 0.078 Uiso 1 1 calc R . .
C3 C -0.0128(4) 0.2613(3) 0.6016(3) 0.0493(9) Uani 1 1 d . . .
H3A H -0.0015 0.2685 0.6727 0.074 Uiso 1 1 calc R . .
H3B H -0.1075 0.2298 0.5603 0.074 Uiso 1 1 calc R . .
H3C H 0.0174 0.3325 0.5910 0.074 Uiso 1 1 calc R . .
C30 C -0.1301(4) 0.3647(3) 0.1567(3) 0.0515(9) Uani 1 1 d . . .
H30 H -0.2133 0.3175 0.1476 0.062 Uiso 1 1 calc R . .
C16 C 0.1062(4) 0.1500(4) 1.0799(3) 0.0531(10) Uani 1 1 d . . .
H16 H 0.0927 0.1627 1.1425 0.064 Uiso 1 1 calc R . .
C31 C -0.1228(4) 0.4370(4) 0.1022(3) 0.0578(11) Uani 1 1 d . . .
H31 H -0.1987 0.4428 0.0514 0.069 Uiso 1 1 calc R . .
C10 C 0.6671(4) 0.1799(4) 0.8265(4) 0.0673(12) Uani 1 1 d . . .
H10 H 0.7435 0.2214 0.8827 0.081 Uiso 1 1 calc R . .
C36 C 0.3431(5) 0.4145(4) 0.7296(3) 0.0590(11) Uani 1 1 d . . .
H36 H 0.3460 0.4151 0.7961 0.071 Uiso 1 1 calc R . .
C1 C 0.1356(4) 0.0820(4) 0.3383(3) 0.0548(10) Uani 1 1 d . . .
H1A H 0.1873 0.0302 0.3279 0.082 Uiso 1 1 calc R . .
H1B H 0.1770 0.1506 0.3282 0.082 Uiso 1 1 calc R . .
H1C H 0.0437 0.0540 0.2902 0.082 Uiso 1 1 calc R . .
C37 C 0.2766(4) 0.4807(4) 0.6786(3) 0.0530(10) Uani 1 1 d . . .
H37 H 0.2350 0.5257 0.7107 0.064 Uiso 1 1 calc R . .
C15 C 0.0533(4) 0.2054(4) 1.0080(3) 0.0530(9) Uani 1 1 d . . .
H15 H 0.0029 0.2540 1.0220 0.064 Uiso 1 1 calc R . .
C11 C 0.6747(5) 0.1478(4) 0.7336(4) 0.0652(12) Uani 1 1 d . . .
H11 H 0.7555 0.1671 0.7206 0.078 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
S1 C11 1.649(5) . ?
S1 C8 1.695(3) . ?
S2 C31 1.651(5) . ?
S2 C28 1.667(3) . ?
C29 C30 1.508(4) . ?
C29 C28 1.573(4) . ?
C29 H29 0.9300 . ?
N4 C12 1.351(4) . ?
N4 C7 1.459(4) . ?
N4 C20 1.473(4) . ?
C9 C10 1.509(5) . ?
C9 C8 1.558(4) . ?
C9 H9 0.9300 . ?
O3 C26 1.227(4) . ?
N7 C32 1.315(4) . ?
N7 C24 1.366(4) . ?
N6 C24 1.384(3) . ?
N6 C22 1.392(4) . ?
N6 C23 1.460(4) . ?
O4 C22 1.203(4) . ?
N5 C22 1.380(4) . ?
N5 C26 1.403(4) . ?
N5 C21 1.455(4) . ?
N8 C32 1.345(3) . ?
N8 C40 1.469(4) . ?
N8 C27 1.473(3) . ?
N3 C12 1.319(4) . ?
N3 C4 1.356(4) . ?
C25 C24 1.359(4) . ?
C25 C26 1.428(4) . ?
C25 C27 1.497(4) . ?
O1 C6 1.226(4) . ?
C27 C28 1.511(4) . ?
C27 H27 0.9800 . ?
C4 C5 1.373(4) . ?
C4 N2 1.383(4) . ?
N2 C2 1.376(4) . ?
N2 C3 1.452(4) . ?
N1 C2 1.378(5) . ?
N1 C6 1.407(4) . ?
N1 C1 1.468(4) . ?
O2 C2 1.244(4) . ?
C13 C14 1.401(4) . ?
C13 C18 1.403(4) . ?
C13 C12 1.480(4) . ?
C8 C7 1.515(4) . ?
C32 C33 1.484(4) . ?
C33 C34 1.389(4) . ?
C33 C38 1.392(4) . ?
C7 C5 1.511(4) . ?
C7 H7 0.9800 . ?
C5 C6 1.424(4) . ?
C34 C35 1.375(5) . ?
C34 H34 0.9300 . ?
C38 C37 1.406(5) . ?
C38 C39 1.483(5) . ?
C14 C15 1.368(5) . ?
C14 H14 0.9300 . ?
C18 C17 1.400(5) . ?
C18 C19 1.498(5) . ?
C20 C19 1.519(5) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C40 C39 1.510(5) . ?
C40 H40A 0.9700 . ?
C40 H40B 0.9700 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C39 H39A 0.9700 . ?
C39 H39B 0.9700 . ?
C17 C16 1.386(6) . ?
C17 H17 0.9300 . ?
C35 C36 1.377(6) . ?
C35 H35 0.9300 . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?
C30 C31 1.311(6) . ?
C30 H30 0.9300 . ?
C16 C15 1.385(6) . ?
C16 H16 0.9300 . ?
C31 H31 0.9300 . ?
C10 C11 1.336(7) . ?
C10 H10 0.9300 . ?
C36 C37 1.372(6) . ?
C36 H36 0.9300 . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C37 H37 0.9300 . ?
C15 H15 0.9300 . ?
C11 H11 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
C11 S1 C8 93.2(2) . . ?
C31 S2 C28 94.08(19) . . ?
C30 C29 C28 100.1(2) . . ?
C30 C29 H29 130.0 . . ?
C28 C29 H29 130.0 . . ?
C12 N4 C7 121.8(2) . . ?
C12 N4 C20 121.2(2) . . ?
C7 N4 C20 116.9(2) . . ?
C10 C9 C8 101.1(3) . . ?
C10 C9 H9 129.4 . . ?
C8 C9 H9 129.4 . . ?
C32 N7 C24 116.2(2) . . ?
C24 N6 C22 122.4(2) . . ?
C24 N6 C23 121.8(3) . . ?
C22 N6 C23 115.8(3) . . ?
C22 N5 C26 124.8(3) . . ?
C22 N5 C21 117.4(3) . . ?
C26 N5 C21 117.7(3) . . ?
C32 N8 C40 121.7(2) . . ?
C32 N8 C27 122.4(2) . . ?
C40 N8 C27 115.9(2) . . ?
C12 N3 C4 116.3(2) . . ?
C24 C25 C26 121.2(3) . . ?
C24 C25 C27 120.1(2) . . ?
C26 C25 C27 118.7(2) . . ?
N8 C27 C25 108.8(2) . . ?
N8 C27 C28 109.7(2) . . ?
C25 C27 C28 113.7(2) . . ?
N8 C27 H27 108.2 . . ?
C25 C27 H27 108.2 . . ?
C28 C27 H27 108.2 . . ?
N3 C4 C5 124.1(3) . . ?
N3 C4 N2 115.7(3) . . ?
C5 C4 N2 120.2(3) . . ?
C2 N2 C4 121.5(3) . . ?
C2 N2 C3 117.4(3) . . ?
C4 N2 C3 121.0(3) . . ?
C2 N1 C6 124.1(3) . . ?
C2 N1 C1 117.9(3) . . ?
C6 N1 C1 117.9(3) . . ?
C25 C24 N7 124.6(2) . . ?
C25 C24 N6 120.0(3) . . ?
N7 C24 N6 115.3(2) . . ?
C27 C28 C29 124.9(2) . . ?
C27 C28 S2 121.6(2) . . ?
C29 C28 S2 113.4(2) . . ?
C14 C13 C18 120.3(3) . . ?
C14 C13 C12 119.5(3) . . ?
C18 C13 C12 120.2(3) . . ?
O3 C26 N5 120.1(3) . . ?
O3 C26 C25 124.4(3) . . ?
N5 C26 C25 115.5(3) . . ?
C7 C8 C9 124.5(2) . . ?
C7 C8 S1 121.9(2) . . ?
C9 C8 S1 113.6(2) . . ?
N7 C32 N8 124.5(2) . . ?
N7 C32 C33 117.9(2) . . ?
N8 C32 C33 117.6(2) . . ?
C34 C33 C38 119.9(3) . . ?
C34 C33 C32 120.5(3) . . ?
C38 C33 C32 119.6(3) . . ?
N4 C7 C5 108.3(2) . . ?
N4 C7 C8 111.1(2) . . ?
C5 C7 C8 111.8(2) . . ?
N4 C7 H7 108.6 . . ?
C5 C7 H7 108.6 . . ?
C8 C7 H7 108.6 . . ?
N3 C12 N4 124.3(3) . . ?
N3 C12 C13 117.2(2) . . ?
N4 C12 C13 118.4(2) . . ?
C4 C5 C6 121.2(3) . . ?
C4 C5 C7 119.1(3) . . ?
C6 C5 C7 119.7(3) . . ?
C35 C34 C33 121.1(4) . . ?
C35 C34 H34 119.4 . . ?
C33 C34 H34 119.4 . . ?
O4 C22 N5 122.1(3) . . ?
O4 C22 N6 121.9(3) . . ?
N5 C22 N6 115.9(2) . . ?
C33 C38 C37 118.3(3) . . ?
C33 C38 C39 119.4(3) . . ?
C37 C38 C39 122.2(3) . . ?
O1 C6 N1 120.1(3) . . ?
O1 C6 C5 124.7(3) . . ?
N1 C6 C5 115.2(3) . . ?
C15 C14 C13 120.0(3) . . ?
C15 C14 H14 120.0 . . ?
C13 C14 H14 120.0 . . ?
C17 C18 C13 118.7(3) . . ?
C17 C18 C19 121.5(3) . . ?
C13 C18 C19 119.6(3) . . ?
O2 C2 N2 121.1(3) . . ?
O2 C2 N1 121.3(3) . . ?
N2 C2 N1 117.5(3) . . ?
N4 C20 C19 111.4(3) . . ?
N4 C20 H20A 109.3 . . ?
C19 C20 H20A 109.3 . . ?
N4 C20 H20B 109.3 . . ?
C19 C20 H20B 109.3 . . ?
H20A C20 H20B 108.0 . . ?
N8 C40 C39 110.0(3) . . ?
N8 C40 H40A 109.7 . . ?
C39 C40 H40A 109.7 . . ?
N8 C40 H40B 109.7 . . ?
C39 C40 H40B 109.7 . . ?
H40A C40 H40B 108.2 . . ?
N5 C21 H21A 109.5 . . ?
N5 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
N5 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C38 C39 C40 110.3(3) . . ?
C38 C39 H39A 109.6 . . ?
C40 C39 H39A 109.6 . . ?
C38 C39 H39B 109.6 . . ?
C40 C39 H39B 109.6 . . ?
H39A C39 H39B 108.1 . . ?
C16 C17 C18 120.1(3) . . ?
C16 C17 H17 119.9 . . ?
C18 C17 H17 119.9 . . ?
C34 C35 C36 119.2(4) . . ?
C34 C35 H35 120.4 . . ?
C36 C35 H35 120.4 . . ?
C18 C19 C20 111.7(3) . . ?
C18 C19 H19A 109.3 . . ?
C20 C19 H19A 109.3 . . ?
C18 C19 H19B 109.3 . . ?
C20 C19 H19B 109.3 . . ?
H19A C19 H19B 107.9 . . ?
N6 C23 H23A 109.5 . . ?
N6 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
N6 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
N2 C3 H3A 109.5 . . ?
N2 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
N2 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C31 C30 C29 117.9(3) . . ?
C31 C30 H30 121.1 . . ?
C29 C30 H30 121.1 . . ?
C15 C16 C17 120.4(3) . . ?
C15 C16 H16 119.8 . . ?
C17 C16 H16 119.8 . . ?
C30 C31 S2 114.6(3) . . ?
C30 C31 H31 122.7 . . ?
S2 C31 H31 122.7 . . ?
C11 C10 C9 116.6(4) . . ?
C11 C10 H10 121.7 . . ?
C9 C10 H10 121.7 . . ?
C37 C36 C35 120.8(3) . . ?
C37 C36 H36 119.6 . . ?
C35 C36 H36 119.6 . . ?
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C36 C37 C38 120.6(4) . . ?
C36 C37 H37 119.7 . . ?
C38 C37 H37 119.7 . . ?
C14 C15 C16 120.4(4) . . ?
C14 C15 H15 119.8 . . ?
C16 C15 H15 119.8 . . ?
C10 C11 S1 115.4(3) . . ?
C10 C11 H11 122.3 . . ?
S1 C11 H11 122.3 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C32 N8 C27 C25 -20.3(4) . . . . ?
C40 N8 C27 C25 160.7(3) . . . . ?
C32 N8 C27 C28 104.6(3) . . . . ?
C40 N8 C27 C28 -74.4(3) . . . . ?
C24 C25 C27 N8 15.6(4) . . . . ?
C26 C25 C27 N8 -161.4(3) . . . . ?
C24 C25 C27 C28 -106.8(3) . . . . ?
C26 C25 C27 C28 76.1(3) . . . . ?
C12 N3 C4 C5 -12.3(4) . . . . ?
C12 N3 C4 N2 165.9(3) . . . . ?
N3 C4 N2 C2 179.3(3) . . . . ?
C5 C4 N2 C2 -2.3(5) . . . . ?
N3 C4 N2 C3 -3.4(4) . . . . ?
C5 C4 N2 C3 174.9(3) . . . . ?
C26 C25 C24 N7 175.1(3) . . . . ?
C27 C25 C24 N7 -1.9(4) . . . . ?
C26 C25 C24 N6 -3.5(4) . . . . ?
C27 C25 C24 N6 179.6(3) . . . . ?
C32 N7 C24 C25 -9.7(4) . . . . ?
C32 N7 C24 N6 168.9(2) . . . . ?
C22 N6 C24 C25 2.8(4) . . . . ?
C23 N6 C24 C25 -178.6(3) . . . . ?
C22 N6 C24 N7 -175.9(3) . . . . ?
C23 N6 C24 N7 2.7(4) . . . . ?
N8 C27 C28 C29 -43.6(3) . . . . ?
C25 C27 C28 C29 78.4(3) . . . . ?
N8 C27 C28 S2 138.9(2) . . . . ?
C25 C27 C28 S2 -99.1(3) . . . . ?
C30 C29 C28 C27 -177.6(3) . . . . ?
C30 C29 C28 S2 0.1(3) . . . . ?
C31 S2 C28 C27 176.8(3) . . . . ?
C31 S2 C28 C29 -1.0(2) . . . . ?
C22 N5 C26 O3 176.1(3) . . . . ?
C21 N5 C26 O3 -2.0(5) . . . . ?
C22 N5 C26 C25 -3.6(4) . . . . ?
C21 N5 C26 C25 178.2(3) . . . . ?
C24 C25 C26 O3 -176.0(3) . . . . ?
C27 C25 C26 O3 1.0(5) . . . . ?
C24 C25 C26 N5 3.8(4) . . . . ?
C27 C25 C26 N5 -179.2(3) . . . . ?
C10 C9 C8 C7 179.9(3) . . . . ?
C10 C9 C8 S1 -2.7(3) . . . . ?
C11 S1 C8 C7 179.2(3) . . . . ?
C11 S1 C8 C9 1.8(3) . . . . ?
C24 N7 C32 N8 5.1(4) . . . . ?
C24 N7 C32 C33 -173.4(2) . . . . ?
C40 N8 C32 N7 -170.0(3) . . . . ?
C27 N8 C32 N7 11.2(5) . . . . ?
C40 N8 C32 C33 8.5(4) . . . . ?
C27 N8 C32 C33 -170.4(3) . . . . ?
N7 C32 C33 C34 9.6(4) . . . . ?
N8 C32 C33 C34 -169.0(3) . . . . ?
N7 C32 C33 C38 -168.9(3) . . . . ?
N8 C32 C33 C38 12.6(4) . . . . ?
C12 N4 C7 C5 -26.0(4) . . . . ?
C20 N4 C7 C5 149.8(3) . . . . ?
C12 N4 C7 C8 97.1(3) . . . . ?
C20 N4 C7 C8 -87.1(3) . . . . ?
C9 C8 C7 N4 -7.6(4) . . . . ?
S1 C8 C7 N4 175.2(2) . . . . ?
C9 C8 C7 C5 113.4(3) . . . . ?
S1 C8 C7 C5 -63.8(3) . . . . ?
C4 N3 C12 N4 9.4(5) . . . . ?
C4 N3 C12 C13 -168.8(3) . . . . ?
C7 N4 C12 N3 11.5(5) . . . . ?
C20 N4 C12 N3 -164.1(3) . . . . ?
C7 N4 C12 C13 -170.3(3) . . . . ?
C20 N4 C12 C13 14.1(4) . . . . ?
C14 C13 C12 N3 4.7(4) . . . . ?
C18 C13 C12 N3 -174.4(3) . . . . ?
C14 C13 C12 N4 -173.7(3) . . . . ?
C18 C13 C12 N4 7.2(5) . . . . ?
N3 C4 C5 C6 177.5(3) . . . . ?
N2 C4 C5 C6 -0.7(5) . . . . ?
N3 C4 C5 C7 -5.0(5) . . . . ?
N2 C4 C5 C7 176.8(3) . . . . ?
N4 C7 C5 C4 22.5(4) . . . . ?
C8 C7 C5 C4 -100.2(3) . . . . ?
N4 C7 C5 C6 -159.9(3) . . . . ?
C8 C7 C5 C6 77.4(3) . . . . ?
C38 C33 C34 C35 -1.2(5) . . . . ?
C32 C33 C34 C35 -179.6(3) . . . . ?
C26 N5 C22 O4 -178.2(3) . . . . ?
C21 N5 C22 O4 0.0(5) . . . . ?
C26 N5 C22 N6 2.9(4) . . . . ?
C21 N5 C22 N6 -178.9(3) . . . . ?
C24 N6 C22 O4 178.8(3) . . . . ?
C23 N6 C22 O4 0.1(5) . . . . ?
C24 N6 C22 N5 -2.4(4) . . . . ?
C23 N6 C22 N5 178.9(3) . . . . ?
C34 C33 C38 C37 1.3(5) . . . . ?
C32 C33 C38 C37 179.7(3) . . . . ?
C34 C33 C38 C39 -175.9(3) . . . . ?
C32 C33 C38 C39 2.6(5) . . . . ?
C2 N1 C6 O1 175.2(3) . . . . ?
C1 N1 C6 O1 -4.4(5) . . . . ?
C2 N1 C6 C5 -5.6(5) . . . . ?
C1 N1 C6 C5 174.8(3) . . . . ?
C4 C5 C6 O1 -176.4(3) . . . . ?
C7 C5 C6 O1 6.0(5) . . . . ?
C4 C5 C6 N1 4.4(4) . . . . ?
C7 C5 C6 N1 -173.1(3) . . . . ?
C18 C13 C14 C15 1.5(5) . . . . ?
C12 C13 C14 C15 -177.6(3) . . . . ?
C14 C13 C18 C17 -0.4(5) . . . . ?
C12 C13 C18 C17 178.7(3) . . . . ?
C14 C13 C18 C19 -177.3(3) . . . . ?
C12 C13 C18 C19 1.8(5) . . . . ?
C4 N2 C2 O2 179.7(3) . . . . ?
C3 N2 C2 O2 2.3(5) . . . . ?
C4 N2 C2 N1 1.3(5) . . . . ?
C3 N2 C2 N1 -176.0(3) . . . . ?
C6 N1 C2 O2 -175.5(3) . . . . ?
C1 N1 C2 O2 4.2(5) . . . . ?
C6 N1 C2 N2 2.9(5) . . . . ?
C1 N1 C2 N2 -177.5(3) . . . . ?
C12 N4 C20 C19 -41.8(4) . . . . ?
C7 N4 C20 C19 142.4(3) . . . . ?
C32 N8 C40 C39 -41.4(4) . . . . ?
C27 N8 C40 C39 137.6(3) . . . . ?
C33 C38 C39 C40 -35.3(5) . . . . ?
C37 C38 C39 C40 147.7(4) . . . . ?
N8 C40 C39 C38 52.3(4) . . . . ?
C13 C18 C17 C16 -1.5(5) . . . . ?
C19 C18 C17 C16 175.3(3) . . . . ?
C33 C34 C35 C36 0.4(5) . . . . ?
C17 C18 C19 C20 154.0(3) . . . . ?
C13 C18 C19 C20 -29.2(5) . . . . ?
N4 C20 C19 C18 46.9(4) . . . . ?
C28 C29 C30 C31 1.2(4) . . . . ?
C18 C17 C16 C15 2.3(6) . . . . ?
C29 C30 C31 S2 -2.1(5) . . . . ?
C28 S2 C31 C30 1.7(3) . . . . ?
C8 C9 C10 C11 2.8(5) . . . . ?
C34 C35 C36 C37 0.2(6) . . . . ?
C35 C36 C37 C38 -0.1(6) . . . . ?
C33 C38 C37 C36 -0.7(6) . . . . ?
C39 C38 C37 C36 176.4(4) . . . . ?
C13 C14 C15 C16 -0.6(6) . . . . ?
C17 C16 C15 C14 -1.3(6) . . . . ?
C9 C10 C11 S1 -1.9(6) . . . . ?
C8 S1 C11 C10 0.0(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        29.12
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         2.196
_refine_diff_density_min         -0.945
_refine_diff_density_rms         0.142
####################################################################### 
# 
# 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_PARAN_12_0m
_database_code_depnum_ccdc_archive 'CCDC 1850631'
_audit_update_record             
;
2018-06-20 deposited with the CCDC.
2018-11-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H26 N4 O2'
_chemical_formula_sum            'C26 H26 N4 O2'
_chemical_formula_weight         426.51

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

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

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

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

_cell_length_a                   20.3152(9)
_cell_length_b                   14.7532(6)
_cell_length_c                   16.3900(7)
_cell_angle_alpha                90
_cell_angle_beta                 110.119(2)
_cell_angle_gamma                90
_cell_volume                     4612.6(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4180
_cell_measurement_theta_min      2.40
_cell_measurement_theta_max      26.89

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.228
_exptl_crystal_F_000             1808
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.080
_shelx_estimated_absorpt_T_min   0.983
_shelx_estimated_absorpt_T_max   0.991
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.984
_exptl_absorpt_correction_T_max  0.989
_exptl_absorpt_process_details   'Bruker AXS SADABS program'
_exptl_absorpt_special_details   'Sheldrick,G.M.,2015,University of gottingen'
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            23524
_diffrn_reflns_av_unetI/netI     0.0503
_diffrn_reflns_av_R_equivalents  0.0454
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         1.745
_diffrn_reflns_theta_max         29.027
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             6109
_reflns_number_gt                3578
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1455P)²+1.1999P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6109
_refine_ls_number_parameters     291
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1311
_refine_ls_R_factor_gt           0.0772
_refine_ls_wR_factor_ref         0.2566
_refine_ls_wR_factor_gt          0.2099
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_restrained_S_all      1.050
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.40947(14) 0.08812(17) 0.0571(2) 0.0768(10) Uani 1 1 d . . . . .
H1 H 0.364747 0.066983 0.025828 0.092 Uiso 1 1 calc R U . . .
C2 C 0.4608(2) 0.0314(3) 0.0908(5) 0.223(4) Uani 1 1 d . . . . .
H2 H 0.452670 -0.030149 0.079413 0.268 Uiso 1 1 calc R U . . .
C3 C 0.53168(13) 0.06144(18) 0.14665(18) 0.0627(8) Uani 1 1 d . . . . .
C4 C 0.58679(15) 0.0017(2) 0.1842(2) 0.0730(9) Uani 1 1 d . . . . .
H4 H 0.580201 -0.060017 0.172608 0.088 Uiso 1 1 calc R U . . .
C5 C 0.65025(13) 0.0321(2) 0.23781(18) 0.0626(7) Uani 1 1 d . . . . .
H5 H 0.686828 -0.008482 0.261888 0.075 Uiso 1 1 calc R U . . .
C6 C 0.65990(14) 0.1221(2) 0.2559(2) 0.0812(10) Uani 1 1 d . . . . .
H6 H 0.702684 0.142908 0.293913 0.097 Uiso 1 1 calc R U . . .
C7 C 0.60598(13) 0.18292(19) 0.2179(2) 0.0709(9) Uani 1 1 d . . . . .
H7 H 0.613071 0.244459 0.230000 0.085 Uiso 1 1 calc R U . . .
C8 C 0.54177(10) 0.15297(15) 0.16197(14) 0.0393(5) Uani 1 1 d . . . . .
C9 C 0.48561(10) 0.21867(15) 0.11902(13) 0.0375(5) Uani 1 1 d . . . . .
C10 C 0.44687(10) 0.36458(14) 0.09855(13) 0.0341(4) Uani 1 1 d . . . . .
C11 C 0.38066(10) 0.34039(14) 0.04649(13) 0.0366(5) Uani 1 1 d . . . . .
C12 C 0.36758(10) 0.24496(14) 0.01167(14) 0.0390(5) Uani 1 1 d . . . . .
H12 H 0.322159 0.224660 0.013443 0.047 Uiso 1 1 calc R U . . .
C13 C 0.36616(12) 0.23897(14) -0.08136(14) 0.0435(5) Uani 1 1 d . . . . .
C14 C 0.30602(14) 0.21315(17) -0.14814(17) 0.0612(7) Uani 1 1 d . . . . .
H14 H 0.266112 0.196944 -0.136016 0.073 Uiso 1 1 calc R U . . .
C15 C 0.3052(2) 0.2114(2) -0.2340(2) 0.0818(11) Uani 1 1 d . . . . .
H15 H 0.264848 0.193324 -0.278660 0.098 Uiso 1 1 calc R U . . .
C16 C 0.3637(3) 0.2362(2) -0.2523(2) 0.0853(11) Uani 1 1 d . . . . .
H16 H 0.362410 0.236876 -0.309604 0.102 Uiso 1 1 calc R U . . .
C17 C 0.4240(2) 0.2599(2) -0.1866(2) 0.0743(9) Uani 1 1 d . . . . .
H17 H 0.463930 0.275121 -0.199015 0.089 Uiso 1 1 calc R U . . .
C18 C 0.42532(14) 0.26132(18) -0.10224(17) 0.0560(6) Uani 1 1 d . . . . .
H18 H 0.466510 0.277476 -0.058044 0.067 Uiso 1 1 calc R U . . .
C19 C 0.53476(10) 0.48058(16) 0.17223(13) 0.0404(5) Uani 1 1 d . . . . .
H19B H 0.554121 0.436012 0.217709 0.049 Uiso 1 1 calc R U . . .
H19A H 0.534025 0.538476 0.199955 0.049 Uiso 1 1 calc R U . . .
C20 C 0.58204(11) 0.48793(18) 0.11875(15) 0.0462(5) Uani 1 1 d . . . . .
H20B H 0.565452 0.535999 0.076212 0.055 Uiso 1 1 calc R U . . .
H20A H 0.580965 0.431558 0.087866 0.055 Uiso 1 1 calc R U . . .
C21 C 0.65660(13) 0.5080(2) 0.17740(19) 0.0644(8) Uani 1 1 d . . . . .
H21A H 0.657260 0.562818 0.209295 0.097 Uiso 1 1 calc R U . . .
H21C H 0.685882 0.515308 0.142694 0.097 Uiso 1 1 calc R U . . .
H21B H 0.673806 0.458739 0.217284 0.097 Uiso 1 1 calc R U . . .
C22 C 0.41254(11) 0.52224(15) 0.09422(15) 0.0417(5) Uani 1 1 d . . . . .
C23 C 0.32594(10) 0.40524(15) 0.01943(15) 0.0406(5) Uani 1 1 d . . . . .
C24 C 0.29054(13) 0.56564(18) 0.01409(17) 0.0536(6) Uani 1 1 d . . . . .
H24B H 0.258556 0.548589 -0.042916 0.064 Uiso 1 1 calc R U . . .
H24A H 0.312703 0.622259 0.008040 0.064 Uiso 1 1 calc R U . . .
C25 C 0.24957(15) 0.5800(2) 0.0737(2) 0.0647(7) Uani 1 1 d . . . . .
H25A H 0.280367 0.603363 0.128934 0.078 Uiso 1 1 calc R U . . .
H25B H 0.230756 0.522545 0.084259 0.078 Uiso 1 1 calc R U . . .
C26 C 0.18947(18) 0.6468(3) 0.0337(3) 0.0947(12) Uani 1 1 d . . . . .
H26A H 0.208298 0.704881 0.026893 0.142 Uiso 1 1 calc R U . . .
H26B H 0.162368 0.652713 0.071233 0.142 Uiso 1 1 calc R U . . .
H26C H 0.160045 0.624833 -0.022015 0.142 Uiso 1 1 calc R U . . .
N1 N 0.42302(9) 0.18562(12) 0.06896(12) 0.0412(4) Uani 1 1 d . . . . .
N2 N 0.50098(8) 0.30537(12) 0.13226(11) 0.0392(4) Uani 1 1 d . . . . .
N3 N 0.46244(8) 0.45461(12) 0.12097(11) 0.0372(4) Uani 1 1 d . . . . .
N4 N 0.34513(9) 0.49470(12) 0.04563(12) 0.0434(5) Uani 1 1 d . . . . .
O1 O 0.42687(9) 0.60174(12) 0.11267(13) 0.0607(5) Uani 1 1 d . . . . .
O2 O 0.26446(8) 0.38753(11) -0.02549(12) 0.0563(5) 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 1.302(4) . ?
C1 N1 1.465(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.485(4) . ?
C2 H2 0.9300 . ?
C3 C8 1.376(3) . ?
C3 C4 1.391(3) . ?
C4 C5 1.362(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.360(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.387(4) . ?
C6 H6 0.9300 . ?
C7 C8 1.383(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.478(3) . ?
C9 N2 1.317(3) . ?
C9 N1 1.345(3) . ?
C10 N2 1.363(3) . ?
C10 C11 1.369(3) . ?
C10 N3 1.385(3) . ?
C11 C23 1.417(3) . ?
C11 C12 1.508(3) . ?
C12 N1 1.480(3) . ?
C12 C13 1.518(3) . ?
C12 H12 0.9800 . ?
C13 C14 1.384(3) . ?
C13 C18 1.397(4) . ?
C14 C15 1.402(4) . ?
C14 H14 0.9300 . ?
C15 C16 1.372(6) . ?
C15 H15 0.9300 . ?
C16 C17 1.370(5) . ?
C16 H16 0.9300 . ?
C17 C18 1.373(4) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C19 N3 1.470(2) . ?
C19 C20 1.511(3) . ?
C19 H19B 0.9700 . ?
C19 H19A 0.9700 . ?
C20 C21 1.518(3) . ?
C20 H20B 0.9700 . ?
C20 H20A 0.9700 . ?
C21 H21A 0.9600 . ?
C21 H21C 0.9600 . ?
C21 H21B 0.9600 . ?
C22 O1 1.221(3) . ?
C22 N3 1.382(3) . ?
C22 N4 1.387(3) . ?
C23 O2 1.240(2) . ?
C23 N4 1.401(3) . ?
C24 N4 1.483(3) . ?
C24 C25 1.500(4) . ?
C24 H24B 0.9700 . ?
C24 H24A 0.9700 . ?
C25 C26 1.530(4) . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 N1 119.2(3) . . ?
C2 C1 H1 120.4 . . ?
N1 C1 H1 120.4 . . ?
C1 C2 C3 122.3(3) . . ?
C1 C2 H2 118.8 . . ?
C3 C2 H2 118.8 . . ?
C8 C3 C4 119.6(2) . . ?
C8 C3 C2 117.2(2) . . ?
C4 C3 C2 123.1(3) . . ?
C5 C4 C3 121.0(3) . . ?
C5 C4 H4 119.5 . . ?
C3 C4 H4 119.5 . . ?
C6 C5 C4 119.7(2) . . ?
C6 C5 H5 120.1 . . ?
C4 C5 H5 120.1 . . ?
C5 C6 C7 120.1(3) . . ?
C5 C6 H6 120.0 . . ?
C7 C6 H6 120.0 . . ?
C8 C7 C6 120.7(3) . . ?
C8 C7 H7 119.7 . . ?
C6 C7 H7 119.7 . . ?
C3 C8 C7 118.8(2) . . ?
C3 C8 C9 120.98(19) . . ?
C7 C8 C9 120.2(2) . . ?
N2 C9 N1 124.98(19) . . ?
N2 C9 C8 117.27(18) . . ?
N1 C9 C8 117.7(2) . . ?
N2 C10 C11 124.59(19) . . ?
N2 C10 N3 115.34(17) . . ?
C11 C10 N3 120.06(18) . . ?
C10 C11 C23 121.04(19) . . ?
C10 C11 C12 119.12(18) . . ?
C23 C11 C12 119.65(17) . . ?
N1 C12 C11 108.40(16) . . ?
N1 C12 C13 110.51(17) . . ?
C11 C12 C13 112.00(17) . . ?
N1 C12 H12 108.6 . . ?
C11 C12 H12 108.6 . . ?
C13 C12 H12 108.6 . . ?
C14 C13 C18 118.1(2) . . ?
C14 C13 C12 121.1(2) . . ?
C18 C13 C12 120.8(2) . . ?
C13 C14 C15 120.1(3) . . ?
C13 C14 H14 119.9 . . ?
C15 C14 H14 119.9 . . ?
C16 C15 C14 120.1(3) . . ?
C16 C15 H15 119.9 . . ?
C14 C15 H15 119.9 . . ?
C17 C16 C15 120.2(3) . . ?
C17 C16 H16 119.9 . . ?
C15 C16 H16 119.9 . . ?
C16 C17 C18 119.9(3) . . ?
C16 C17 H17 120.0 . . ?
C18 C17 H17 120.0 . . ?
C17 C18 C13 121.5(3) . . ?
C17 C18 H18 119.3 . . ?
C13 C18 H18 119.3 . . ?
N3 C19 C20 113.39(17) . . ?
N3 C19 H19B 108.9 . . ?
C20 C19 H19B 108.9 . . ?
N3 C19 H19A 108.9 . . ?
C20 C19 H19A 108.9 . . ?
H19B C19 H19A 107.7 . . ?
C19 C20 C21 109.98(19) . . ?
C19 C20 H20B 109.7 . . ?
C21 C20 H20B 109.7 . . ?
C19 C20 H20A 109.7 . . ?
C21 C20 H20A 109.7 . . ?
H20B C20 H20A 108.2 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21C C21 H21B 109.5 . . ?
O1 C22 N3 121.9(2) . . ?
O1 C22 N4 121.8(2) . . ?
N3 C22 N4 116.25(19) . . ?
O2 C23 N4 119.85(19) . . ?
O2 C23 C11 124.4(2) . . ?
N4 C23 C11 115.74(18) . . ?
N4 C24 C25 112.9(2) . . ?
N4 C24 H24B 109.0 . . ?
C25 C24 H24B 109.0 . . ?
N4 C24 H24A 109.0 . . ?
C25 C24 H24A 109.0 . . ?
H24B C24 H24A 107.8 . . ?
C24 C25 C26 110.6(3) . . ?
C24 C25 H25A 109.5 . . ?
C26 C25 H25A 109.5 . . ?
C24 C25 H25B 109.5 . . ?
C26 C25 H25B 109.5 . . ?
H25A C25 H25B 108.1 . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C9 N1 C1 122.13(19) . . ?
C9 N1 C12 121.73(18) . . ?
C1 N1 C12 115.44(17) . . ?
C9 N2 C10 116.31(17) . . ?
C22 N3 C10 122.16(17) . . ?
C22 N3 C19 118.22(18) . . ?
C10 N3 C19 119.58(17) . . ?
C22 N4 C23 124.58(18) . . ?
C22 N4 C24 117.76(19) . . ?
C23 N4 C24 117.52(18) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 C3 4.7(10) . . . . ?
C1 C2 C3 C8 -0.1(10) . . . . ?
C1 C2 C3 C4 179.0(6) . . . . ?
C8 C3 C4 C5 1.6(5) . . . . ?
C2 C3 C4 C5 -177.4(5) . . . . ?
C3 C4 C5 C6 0.9(5) . . . . ?
C4 C5 C6 C7 -2.0(5) . . . . ?
C5 C6 C7 C8 0.7(5) . . . . ?
C4 C3 C8 C7 -2.9(4) . . . . ?
C2 C3 C8 C7 176.2(5) . . . . ?
C4 C3 C8 C9 176.4(3) . . . . ?
C2 C3 C8 C9 -4.5(5) . . . . ?
C6 C7 C8 C3 1.7(5) . . . . ?
C6 C7 C8 C9 -177.6(3) . . . . ?
C3 C8 C9 N2 -175.3(2) . . . . ?
C7 C8 C9 N2 4.0(3) . . . . ?
C3 C8 C9 N1 4.2(3) . . . . ?
C7 C8 C9 N1 -176.5(2) . . . . ?
N2 C10 C11 C23 175.20(19) . . . . ?
N3 C10 C11 C23 -4.2(3) . . . . ?
N2 C10 C11 C12 -9.9(3) . . . . ?
N3 C10 C11 C12 170.68(18) . . . . ?
C10 C11 C12 N1 22.7(3) . . . . ?
C23 C11 C12 N1 -162.34(18) . . . . ?
C10 C11 C12 C13 -99.5(2) . . . . ?
C23 C11 C12 C13 75.5(2) . . . . ?
N1 C12 C13 C14 122.4(2) . . . . ?
C11 C12 C13 C14 -116.6(2) . . . . ?
N1 C12 C13 C18 -58.9(3) . . . . ?
C11 C12 C13 C18 62.0(3) . . . . ?
C18 C13 C14 C15 -1.1(4) . . . . ?
C12 C13 C14 C15 177.6(2) . . . . ?
C13 C14 C15 C16 -0.7(4) . . . . ?
C14 C15 C16 C17 2.2(5) . . . . ?
C15 C16 C17 C18 -1.8(5) . . . . ?
C16 C17 C18 C13 -0.1(4) . . . . ?
C14 C13 C18 C17 1.5(4) . . . . ?
C12 C13 C18 C17 -177.2(2) . . . . ?
N3 C19 C20 C21 -175.8(2) . . . . ?
C10 C11 C23 O2 -177.8(2) . . . . ?
C12 C11 C23 O2 7.3(3) . . . . ?
C10 C11 C23 N4 3.1(3) . . . . ?
C12 C11 C23 N4 -171.78(18) . . . . ?
N4 C24 C25 C26 -174.4(3) . . . . ?
N2 C9 N1 C1 -180.0(2) . . . . ?
C8 C9 N1 C1 0.6(3) . . . . ?
N2 C9 N1 C12 10.1(3) . . . . ?
C8 C9 N1 C12 -169.41(18) . . . . ?
C2 C1 N1 C9 -5.0(6) . . . . ?
C2 C1 N1 C12 165.6(5) . . . . ?
C11 C12 N1 C9 -23.2(3) . . . . ?
C13 C12 N1 C9 99.9(2) . . . . ?
C11 C12 N1 C1 166.2(2) . . . . ?
C13 C12 N1 C1 -70.7(3) . . . . ?
N1 C9 N2 C10 6.2(3) . . . . ?
C8 C9 N2 C10 -174.31(17) . . . . ?
C11 C10 N2 C9 -6.0(3) . . . . ?
N3 C10 N2 C9 173.43(18) . . . . ?
O1 C22 N3 C10 -178.5(2) . . . . ?
N4 C22 N3 C10 1.9(3) . . . . ?
O1 C22 N3 C19 -0.7(3) . . . . ?
N4 C22 N3 C19 179.66(17) . . . . ?
N2 C10 N3 C22 -177.86(18) . . . . ?
C11 C10 N3 C22 1.6(3) . . . . ?
N2 C10 N3 C19 4.4(3) . . . . ?
C11 C10 N3 C19 -176.11(18) . . . . ?
C20 C19 N3 C22 -98.5(2) . . . . ?
C20 C19 N3 C10 79.3(2) . . . . ?
O1 C22 N4 C23 177.3(2) . . . . ?
N3 C22 N4 C23 -3.0(3) . . . . ?
O1 C22 N4 C24 1.7(3) . . . . ?
N3 C22 N4 C24 -178.64(19) . . . . ?
O2 C23 N4 C22 -178.5(2) . . . . ?
C11 C23 N4 C22 0.6(3) . . . . ?
O2 C23 N4 C24 -2.9(3) . . . . ?
C11 C23 N4 C24 176.22(19) . . . . ?
C25 C24 N4 C22 -94.4(3) . . . . ?
C25 C24 N4 C23 89.6(3) . . . . ?

_refine_diff_density_max         0.779
_refine_diff_density_min         -0.534
_refine_diff_density_rms         0.105



####################################################################### 
# 
# 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_pb_823_0m
_database_code_depnum_ccdc_archive 'CCDC 1850632'
_audit_update_record             
;
2018-06-20 deposited with the CCDC.
2018-11-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H20 N4 O2'
_chemical_formula_sum            'C22 H20 N4 O2'
_chemical_formula_weight         372.42

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

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

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

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

_cell_length_a                   10.9372(7)
_cell_length_b                   9.1286(5)
_cell_length_c                   35.781(2)
_cell_angle_alpha                90
_cell_angle_beta                 95.129(3)
_cell_angle_gamma                90
_cell_volume                     3558.2(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5343
_cell_measurement_theta_min      2.29
_cell_measurement_theta_max      26.02

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.390
_exptl_crystal_F_000             1568
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.190
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.130
_exptl_absorpt_coefficient_mu    0.092
_shelx_estimated_absorpt_T_min   0.983
_shelx_estimated_absorpt_T_max   0.988
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.983
_exptl_absorpt_correction_T_max  0.988
_exptl_absorpt_process_details   'Bruker AXS SADABS program'
_exptl_absorpt_special_details   'Sheldrick,G.M.,2015,University of gottingen'
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            28160
_diffrn_reflns_av_unetI/netI     0.0459
_diffrn_reflns_av_R_equivalents  0.0381
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -48
_diffrn_reflns_limit_l_max       48
_diffrn_reflns_theta_min         1.143
_diffrn_reflns_theta_max         29.044
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             9463
_reflns_number_gt                6112
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1314P)²+0.3617P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_extinction_coef       0.0122(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         9463
_refine_ls_number_parameters     520
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1091
_refine_ls_R_factor_gt           0.0706
_refine_ls_wR_factor_ref         0.2219
_refine_ls_wR_factor_gt          0.1879
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.57324(16) -0.11117(19) 0.07719(5) 0.0567(4) Uani 1 1 d . . . . .
N1 N 0.95535(15) 0.19037(18) 0.18842(4) 0.0354(4) Uani 1 1 d . . . . .
C1 C 0.6094(2) 0.4546(3) 0.24540(8) 0.0607(7) Uani 1 1 d . . . . .
H1 H 0.559219 0.524368 0.255221 0.073 Uiso 1 1 calc R U . . .
O2 O 0.66486(15) -0.10876(17) 0.20389(4) 0.0493(4) Uani 1 1 d . . . . .
N2 N 0.88322(16) 0.19446(18) 0.12422(4) 0.0363(4) Uani 1 1 d . . . . .
C2 C 0.5963(2) 0.3099(3) 0.25399(7) 0.0563(6) Uani 1 1 d . . . . .
H2 H 0.535966 0.280844 0.269184 0.068 Uiso 1 1 calc R U . . .
N3 N 0.72883(16) 0.03570(18) 0.10106(4) 0.0361(4) Uani 1 1 d . . . . .
O3 O -0.07799(18) 0.6718(2) 0.17637(5) 0.0625(5) Uani 1 1 d . . . . .
C3 C 0.6728(2) 0.2068(3) 0.24005(6) 0.0440(5) Uani 1 1 d . . . . .
H3 H 0.664648 0.108777 0.246481 0.053 Uiso 1 1 calc R U . . .
N4 N 0.61996(16) -0.11117(18) 0.14049(5) 0.0385(4) Uani 1 1 d . . . . .
O4 O -0.11931(16) 0.74581(19) 0.05004(5) 0.0547(4) Uani 1 1 d . . . . .
C4 C 0.76195(17) 0.2473(2) 0.21648(5) 0.0331(4) Uani 1 1 d . . . . .
C6 C 0.6978(2) 0.4978(3) 0.22201(7) 0.0519(6) Uani 1 1 d . . . . .
H6 H 0.706366 0.596279 0.216126 0.062 Uiso 1 1 calc R U . . .
N6 N 0.20970(16) 0.96173(18) 0.12709(4) 0.0375(4) Uani 1 1 d . . . . .
C5 C 0.7729(2) 0.3943(2) 0.20747(6) 0.0415(5) Uani 1 1 d . . . . .
H5 H 0.831163 0.423405 0.191571 0.050 Uiso 1 1 calc R U . . .
N5 N 0.19085(17) 1.02853(18) 0.06321(4) 0.0382(4) Uani 1 1 d . . . . .
C7 C 0.84145(17) 0.1292(2) 0.20037(5) 0.0324(4) Uani 1 1 d . . . . .
H7 H 0.862984 0.056866 0.220103 0.039 Uiso 1 1 calc R U . . .
N7 N 0.05988(17) 0.81804(18) 0.15124(5) 0.0382(4) Uani 1 1 d . . . . .
C14 C 1.0717(2) 0.3760(3) 0.10718(7) 0.0517(6) Uani 1 1 d . . . . .
H14 H 1.015982 0.340989 0.088112 0.062 Uiso 1 1 calc R U . . .
C15 C 1.06369(18) 0.3303(2) 0.14390(6) 0.0353(4) Uani 1 1 d . . . . .
C16 C 0.96179(18) 0.2322(2) 0.15248(5) 0.0326(4) Uani 1 1 d . . . . .
C17 C 0.79597(17) 0.0943(2) 0.13210(5) 0.0313(4) Uani 1 1 d . . . . .
C18 C 0.6361(2) -0.0647(2) 0.10440(6) 0.0395(5) Uani 1 1 d . . . . .
C22 C 0.5220(2) -0.2175(3) 0.14447(8) 0.0546(6) Uani 1 1 d . . . . .
H22A H 0.514598 -0.281057 0.123014 0.082 Uiso 1 1 calc R U . . .
H22B H 0.445856 -0.166683 0.146237 0.082 Uiso 1 1 calc R U . . .
H22C H 0.541145 -0.274501 0.166767 0.082 Uiso 1 1 calc R U . . .
C21 C 0.7517(2) 0.0823(3) 0.06303(6) 0.0499(6) Uani 1 1 d . . . . .
H21A H 0.694321 0.034868 0.045092 0.075 Uiso 1 1 calc R U . . .
H21B H 0.833818 0.056048 0.058218 0.075 Uiso 1 1 calc R U . . .
H21C H 0.741910 0.186605 0.060920 0.075 Uiso 1 1 calc R U . . .
C20 C 0.77489(17) 0.0507(2) 0.16736(5) 0.0314(4) Uani 1 1 d . . . . .
C19 C 0.68616(18) -0.0598(2) 0.17306(6) 0.0358(4) Uani 1 1 d . . . . .
C8 C 1.0498(2) 0.2312(3) 0.21809(7) 0.0623(7) Uani 1 1 d . . . . .
H8A H 1.012180 0.238738 0.241557 0.075 Uiso 1 1 calc R U . A 1
H8B H 1.110405 0.153473 0.220862 0.075 Uiso 1 1 calc R U . A 1
N8 N -0.09920(17) 0.70785(19) 0.11307(5) 0.0419(4) Uani 1 1 d . . . . .
C9A C 1.1111(5) 0.3659(6) 0.21166(12) 0.0460(16) Uani 0.505(9) 1 d . . P B 1
H9A1 H 1.183839 0.373336 0.229169 0.055 Uiso 0.505(9) 1 calc R U P B 1
H9A2 H 1.057336 0.446851 0.216561 0.055 Uiso 0.505(9) 1 calc R U P B 1
C9B C 1.1690(5) 0.2777(7) 0.20864(14) 0.0533(18) Uani 0.495(9) 1 d . . P B 2
H9B1 H 1.218798 0.193306 0.203553 0.064 Uiso 0.495(9) 1 calc R U P B 2
H9B2 H 1.210585 0.332317 0.229263 0.064 Uiso 0.495(9) 1 calc R U P B 2
C10 C 1.1483(3) 0.3794(3) 0.17199(7) 0.0607(7) Uani 1 1 d . . . . .
C11 C 1.2380(3) 0.4779(3) 0.16272(9) 0.0721(9) Uani 1 1 d . . . . .
H11 H 1.294922 0.512702 0.181493 0.087 Uiso 1 1 calc R U . . .
C12 C 1.2440(2) 0.5244(3) 0.12693(9) 0.0607(7) Uani 1 1 d . . . . .
H12 H 1.304129 0.591219 0.121475 0.073 Uiso 1 1 calc R U . . .
C13 C 1.1622(3) 0.4734(3) 0.09884(9) 0.0621(7) Uani 1 1 d . . . . .
H13 H 1.167296 0.503972 0.074241 0.075 Uiso 1 1 calc R U . . .
C37 C 0.34684(19) 1.1406(2) 0.10573(6) 0.0359(4) Uani 1 1 d . . . . .
C38 C 0.24342(18) 1.0373(2) 0.09843(5) 0.0334(4) Uani 1 1 d . . . . .
C39 C 0.10683(18) 0.8773(2) 0.11997(5) 0.0330(4) Uani 1 1 d . . . . .
C40 C -0.0413(2) 0.7282(2) 0.14848(6) 0.0420(5) Uani 1 1 d . . . . .
C41 C -0.05987(19) 0.7679(2) 0.08024(6) 0.0390(5) Uani 1 1 d . . . . .
C42 C 0.04989(18) 0.8527(2) 0.08526(5) 0.0342(4) Uani 1 1 d . . . . .
C43 C 0.1202(3) 0.8395(3) 0.18885(6) 0.0606(7) Uani 1 1 d . . . . .
H43A H 0.183887 0.911507 0.188027 0.091 Uiso 1 1 calc R U . . .
H43B H 0.155288 0.748589 0.198024 0.091 Uiso 1 1 calc R U . . .
H43C H 0.061119 0.872620 0.205267 0.091 Uiso 1 1 calc R U . . .
C44 C -0.2051(2) 0.6089(3) 0.10979(8) 0.0557(6) Uani 1 1 d . . . . .
H44A H -0.260900 0.638298 0.088898 0.084 Uiso 1 1 calc R U . . .
H44B H -0.246040 0.613058 0.132404 0.084 Uiso 1 1 calc R U . . .
H44C H -0.177730 0.510621 0.105915 0.084 Uiso 1 1 calc R U . . .
C36 C 0.3934(2) 1.1695(3) 0.14216(7) 0.0485(5) Uani 1 1 d . . . . .
H36 H 0.358078 1.125401 0.162014 0.058 Uiso 1 1 calc R U . . .
C35 C 0.4920(3) 1.2635(3) 0.14942(8) 0.0610(7) Uani 1 1 d . . . . .
H35 H 0.523488 1.281512 0.173999 0.073 Uiso 1 1 calc R U . . .
C34 C 0.5428(2) 1.3294(3) 0.12030(9) 0.0650(8) Uani 1 1 d . . . . .
H34 H 0.607866 1.394202 0.125184 0.078 Uiso 1 1 calc R U . . .
C33 C 0.4995(2) 1.3014(3) 0.08423(9) 0.0627(7) Uani 1 1 d . . . . .
H33 H 0.535527 1.347163 0.064748 0.075 Uiso 1 1 calc R U . . .
C32 C 0.4014(2) 1.2049(2) 0.07594(7) 0.0474(5) Uani 1 1 d . . . . .
C31 C 0.3564(3) 1.1626(3) 0.03670(7) 0.0639(7) Uani 1 1 d . . . . .
H31A H 0.371840 1.242013 0.019737 0.077 Uiso 1 1 calc R U . . .
H31B H 0.401024 1.077125 0.029278 0.077 Uiso 1 1 calc R U . . .
C30 C 0.2235(3) 1.1297(3) 0.03379(6) 0.0554(6) Uani 1 1 d . . . . .
H30A H 0.178102 1.220284 0.035639 0.066 Uiso 1 1 calc R U . . .
H30B H 0.199733 1.086872 0.009412 0.066 Uiso 1 1 calc R U . . .
C29 C 0.10760(19) 0.9081(2) 0.05122(5) 0.0360(4) Uani 1 1 d . . . . .
H29 H 0.042567 0.946642 0.033274 0.043 Uiso 1 1 calc R U . . .
C28 C 0.1672(3) 0.5828(3) -0.01070(7) 0.0660(8) Uani 1 1 d . . . . .
H28 H 0.122134 0.522574 -0.027779 0.079 Uiso 1 1 calc R U . . .
C27 C 0.1112(3) 0.6967(3) 0.00568(6) 0.0514(6) Uani 1 1 d . . . . .
H27 H 0.028306 0.714340 -0.000810 0.062 Uiso 1 1 calc R U . . .
C26 C 0.1758(2) 0.7873(2) 0.03195(5) 0.0389(5) Uani 1 1 d . . . . .
C25 C 0.2996(2) 0.7608(3) 0.04061(7) 0.0501(6) Uani 1 1 d . . . . .
H25 H 0.344468 0.820465 0.057874 0.060 Uiso 1 1 calc R U . . .
C24 C 0.3572(3) 0.6470(3) 0.02395(8) 0.0685(8) Uani 1 1 d . . . . .
H24 H 0.440529 0.630097 0.029943 0.082 Uiso 1 1 calc R U . . .
C23 C 0.2901(4) 0.5572(3) -0.00193(8) 0.0720(9) Uani 1 1 d . . . . .
H23 H 0.328593 0.480125 -0.013211 0.086 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C18 1.217(3) . ?
N1 C16 1.349(2) . ?
N1 C8 1.462(3) . ?
N1 C7 1.463(2) . ?
C1 C2 1.367(4) . ?
C1 C6 1.391(4) . ?
C1 H1 0.9300 . ?
O2 C19 1.231(2) . ?
N2 C16 1.313(3) . ?
N2 C17 1.369(2) . ?
C2 C3 1.381(3) . ?
C2 H2 0.9300 . ?
N3 C18 1.380(3) . ?
N3 C17 1.383(2) . ?
N3 C21 1.468(3) . ?
O3 C40 1.222(3) . ?
C3 C4 1.395(3) . ?
C3 H3 0.9300 . ?
N4 C18 1.385(3) . ?
N4 C19 1.397(3) . ?
N4 C22 1.462(3) . ?
O4 C41 1.227(3) . ?
C4 C5 1.388(3) . ?
C4 C7 1.530(3) . ?
C6 C5 1.384(3) . ?
C6 H6 0.9300 . ?
N6 C38 1.316(2) . ?
N6 C39 1.369(3) . ?
C5 H5 0.9300 . ?
N5 C38 1.340(2) . ?
N5 C29 1.467(3) . ?
N5 C30 1.468(3) . ?
C7 C20 1.512(3) . ?
C7 H7 0.9800 . ?
N7 C40 1.373(3) . ?
N7 C39 1.383(2) . ?
N7 C43 1.458(3) . ?
C14 C13 1.382(3) . ?
C14 C15 1.389(3) . ?
C14 H14 0.9300 . ?
C15 C10 1.379(3) . ?
C15 C16 1.483(3) . ?
C17 C20 1.362(3) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C20 C19 1.427(3) . ?
C8 C9A 1.429(5) . ?
C8 C9B 1.439(6) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
N8 C40 1.378(3) . ?
N8 C41 1.398(3) . ?
N8 C44 1.465(3) . ?
C9A C10 1.516(5) . ?
C9A H9A1 0.9700 . ?
C9A H9A2 0.9700 . ?
C9B C10 1.606(6) . ?
C9B H9B1 0.9700 . ?
C9B H9B2 0.9700 . ?
C10 C11 1.392(3) . ?
C11 C12 1.357(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.367(4) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C37 C36 1.382(3) . ?
C37 C32 1.397(3) . ?
C37 C38 1.478(3) . ?
C39 C42 1.357(3) . ?
C41 C42 1.426(3) . ?
C42 C29 1.508(3) . ?
C43 H43A 0.9600 . ?
C43 H43B 0.9600 . ?
C43 H43C 0.9600 . ?
C44 H44A 0.9600 . ?
C44 H44B 0.9600 . ?
C44 H44C 0.9600 . ?
C36 C35 1.385(3) . ?
C36 H36 0.9300 . ?
C35 C34 1.364(4) . ?
C35 H35 0.9300 . ?
C34 C33 1.359(4) . ?
C34 H34 0.9300 . ?
C33 C32 1.399(3) . ?
C33 H33 0.9300 . ?
C32 C31 1.497(4) . ?
C31 C30 1.478(4) . ?
C31 H31A 0.9700 . ?
C31 H31B 0.9700 . ?
C30 H30A 0.9700 . ?
C30 H30B 0.9700 . ?
C29 C26 1.530(3) . ?
C29 H29 0.9800 . ?
C28 C27 1.365(4) . ?
C28 C23 1.373(5) . ?
C28 H28 0.9300 . ?
C27 C26 1.395(3) . ?
C27 H27 0.9300 . ?
C26 C25 1.383(3) . ?
C25 C24 1.378(4) . ?
C25 H25 0.9300 . ?
C24 C23 1.395(5) . ?
C24 H24 0.9300 . ?
C23 H23 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
C16 N1 C8 121.74(18) . . ?
C16 N1 C7 120.32(16) . . ?
C8 N1 C7 116.73(17) . . ?
C2 C1 C6 120.1(2) . . ?
C2 C1 H1 119.9 . . ?
C6 C1 H1 119.9 . . ?
C16 N2 C17 115.90(16) . . ?
C1 C2 C3 119.9(2) . . ?
C1 C2 H2 120.1 . . ?
C3 C2 H2 120.1 . . ?
C18 N3 C17 121.91(16) . . ?
C18 N3 C21 117.41(17) . . ?
C17 N3 C21 120.66(17) . . ?
C2 C3 C4 121.1(2) . . ?
C2 C3 H3 119.5 . . ?
C4 C3 H3 119.5 . . ?
C18 N4 C19 125.11(16) . . ?
C18 N4 C22 116.71(18) . . ?
C19 N4 C22 118.12(18) . . ?
C5 C4 C3 118.45(19) . . ?
C5 C4 C7 122.00(17) . . ?
C3 C4 C7 119.52(18) . . ?
C5 C6 C1 120.0(2) . . ?
C5 C6 H6 120.0 . . ?
C1 C6 H6 120.0 . . ?
C38 N6 C39 115.67(16) . . ?
C6 C5 C4 120.4(2) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
C38 N5 C29 121.52(16) . . ?
C38 N5 C30 121.68(17) . . ?
C29 N5 C30 116.50(16) . . ?
N1 C7 C20 108.39(14) . . ?
N1 C7 C4 111.64(16) . . ?
C20 C7 C4 112.22(16) . . ?
N1 C7 H7 108.2 . . ?
C20 C7 H7 108.2 . . ?
C4 C7 H7 108.2 . . ?
C40 N7 C39 122.05(18) . . ?
C40 N7 C43 116.21(18) . . ?
C39 N7 C43 121.61(18) . . ?
C13 C14 C15 120.3(2) . . ?
C13 C14 H14 119.9 . . ?
C15 C14 H14 119.9 . . ?
C10 C15 C14 119.8(2) . . ?
C10 C15 C16 120.86(19) . . ?
C14 C15 C16 119.32(19) . . ?
N2 C16 N1 124.98(17) . . ?
N2 C16 C15 116.81(17) . . ?
N1 C16 C15 118.21(18) . . ?
C20 C17 N2 124.37(17) . . ?
C20 C17 N3 120.63(17) . . ?
N2 C17 N3 114.99(16) . . ?
O1 C18 N3 121.9(2) . . ?
O1 C18 N4 121.95(19) . . ?
N3 C18 N4 116.10(17) . . ?
N4 C22 H22A 109.5 . . ?
N4 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
N4 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
N3 C21 H21A 109.5 . . ?
N3 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
N3 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C17 C20 C19 120.82(17) . . ?
C17 C20 C7 118.43(16) . . ?
C19 C20 C7 120.63(16) . . ?
O2 C19 N4 119.98(18) . . ?
O2 C19 C20 124.77(19) . . ?
N4 C19 C20 115.24(17) . . ?
C9A C8 N1 114.4(3) . . ?
C9B C8 N1 120.0(3) . . ?
C9A C8 H8A 108.7 . . ?
N1 C8 H8A 108.7 . . ?
C9A C8 H8B 108.6 . . ?
N1 C8 H8B 108.7 . . ?
H8A C8 H8B 107.6 . . ?
C40 N8 C41 124.67(18) . . ?
C40 N8 C44 116.88(19) . . ?
C41 N8 C44 118.34(19) . . ?
C8 C9A C10 112.9(3) . . ?
C8 C9A H9A1 109.0 . . ?
C10 C9A H9A1 109.0 . . ?
C8 C9A H9A2 109.0 . . ?
C10 C9A H9A2 109.0 . . ?
H9A1 C9A H9A2 107.8 . . ?
C8 C9B C10 107.4(4) . . ?
C8 C9B H9B1 110.2 . . ?
C10 C9B H9B1 110.2 . . ?
C8 C9B H9B2 110.2 . . ?
C10 C9B H9B2 110.2 . . ?
H9B1 C9B H9B2 108.5 . . ?
C15 C10 C11 118.5(2) . . ?
C15 C10 C9A 115.9(3) . . ?
C11 C10 C9A 121.9(3) . . ?
C15 C10 C9B 116.3(3) . . ?
C11 C10 C9B 121.2(3) . . ?
C12 C11 C10 121.5(3) . . ?
C12 C11 H11 119.3 . . ?
C10 C11 H11 119.3 . . ?
C11 C12 C13 120.2(2) . . ?
C11 C12 H12 119.9 . . ?
C13 C12 H12 119.9 . . ?
C12 C13 C14 119.7(3) . . ?
C12 C13 H13 120.2 . . ?
C14 C13 H13 120.2 . . ?
C36 C37 C32 119.6(2) . . ?
C36 C37 C38 119.99(19) . . ?
C32 C37 C38 120.40(19) . . ?
N6 C38 N5 125.10(18) . . ?
N6 C38 C37 117.42(17) . . ?
N5 C38 C37 117.48(17) . . ?
C42 C39 N6 124.46(17) . . ?
C42 C39 N7 120.15(18) . . ?
N6 C39 N7 115.37(17) . . ?
O3 C40 N7 120.9(2) . . ?
O3 C40 N8 122.4(2) . . ?
N7 C40 N8 116.61(18) . . ?
O4 C41 N8 119.78(19) . . ?
O4 C41 C42 125.02(19) . . ?
N8 C41 C42 115.20(18) . . ?
C39 C42 C41 121.16(18) . . ?
C39 C42 C29 119.49(18) . . ?
C41 C42 C29 119.26(17) . . ?
N7 C43 H43A 109.5 . . ?
N7 C43 H43B 109.5 . . ?
H43A C43 H43B 109.5 . . ?
N7 C43 H43C 109.5 . . ?
H43A C43 H43C 109.5 . . ?
H43B C43 H43C 109.5 . . ?
N8 C44 H44A 109.5 . . ?
N8 C44 H44B 109.5 . . ?
H44A C44 H44B 109.5 . . ?
N8 C44 H44C 109.5 . . ?
H44A C44 H44C 109.5 . . ?
H44B C44 H44C 109.5 . . ?
C37 C36 C35 120.7(2) . . ?
C37 C36 H36 119.7 . . ?
C35 C36 H36 119.7 . . ?
C34 C35 C36 119.6(3) . . ?
C34 C35 H35 120.2 . . ?
C36 C35 H35 120.2 . . ?
C33 C34 C35 120.8(2) . . ?
C33 C34 H34 119.6 . . ?
C35 C34 H34 119.6 . . ?
C34 C33 C32 121.0(2) . . ?
C34 C33 H33 119.5 . . ?
C32 C33 H33 119.5 . . ?
C37 C32 C33 118.3(2) . . ?
C37 C32 C31 118.7(2) . . ?
C33 C32 C31 122.9(2) . . ?
C30 C31 C32 111.0(2) . . ?
C30 C31 H31A 109.4 . . ?
C32 C31 H31A 109.4 . . ?
C30 C31 H31B 109.4 . . ?
C32 C31 H31B 109.4 . . ?
H31A C31 H31B 108.0 . . ?
N5 C30 C31 112.2(2) . . ?
N5 C30 H30A 109.2 . . ?
C31 C30 H30A 109.2 . . ?
N5 C30 H30B 109.2 . . ?
C31 C30 H30B 109.2 . . ?
H30A C30 H30B 107.9 . . ?
N5 C29 C42 107.99(15) . . ?
N5 C29 C26 110.93(17) . . ?
C42 C29 C26 112.22(16) . . ?
N5 C29 H29 108.5 . . ?
C42 C29 H29 108.5 . . ?
C26 C29 H29 108.5 . . ?
C27 C28 C23 119.9(3) . . ?
C27 C28 H28 120.0 . . ?
C23 C28 H28 120.0 . . ?
C28 C27 C26 121.4(3) . . ?
C28 C27 H27 119.3 . . ?
C26 C27 H27 119.3 . . ?
C25 C26 C27 118.3(2) . . ?
C25 C26 C29 122.15(19) . . ?
C27 C26 C29 119.5(2) . . ?
C24 C25 C26 120.8(3) . . ?
C24 C25 H25 119.6 . . ?
C26 C25 H25 119.6 . . ?
C25 C24 C23 119.8(3) . . ?
C25 C24 H24 120.1 . . ?
C23 C24 H24 120.1 . . ?
C28 C23 C24 119.9(3) . . ?
C28 C23 H23 120.1 . . ?
C24 C23 H23 120.1 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 1.4(4) . . . . ?
C1 C2 C3 C4 -1.5(4) . . . . ?
C2 C3 C4 C5 0.4(3) . . . . ?
C2 C3 C4 C7 -177.6(2) . . . . ?
C2 C1 C6 C5 -0.2(4) . . . . ?
C1 C6 C5 C4 -0.9(4) . . . . ?
C3 C4 C5 C6 0.8(3) . . . . ?
C7 C4 C5 C6 178.73(19) . . . . ?
C16 N1 C7 C20 30.3(2) . . . . ?
C8 N1 C7 C20 -162.0(2) . . . . ?
C16 N1 C7 C4 -93.8(2) . . . . ?
C8 N1 C7 C4 73.9(2) . . . . ?
C5 C4 C7 N1 23.0(3) . . . . ?
C3 C4 C7 N1 -159.07(18) . . . . ?
C5 C4 C7 C20 -98.9(2) . . . . ?
C3 C4 C7 C20 79.0(2) . . . . ?
C13 C14 C15 C10 -1.7(4) . . . . ?
C13 C14 C15 C16 176.7(2) . . . . ?
C17 N2 C16 N1 -6.4(3) . . . . ?
C17 N2 C16 C15 174.70(16) . . . . ?
C8 N1 C16 N2 177.0(2) . . . . ?
C7 N1 C16 N2 -16.0(3) . . . . ?
C8 N1 C16 C15 -4.1(3) . . . . ?
C7 N1 C16 C15 162.96(16) . . . . ?
C10 C15 C16 N2 178.0(2) . . . . ?
C14 C15 C16 N2 -0.4(3) . . . . ?
C10 C15 C16 N1 -1.1(3) . . . . ?
C14 C15 C16 N1 -179.42(19) . . . . ?
C16 N2 C17 C20 10.5(3) . . . . ?
C16 N2 C17 N3 -168.59(17) . . . . ?
C18 N3 C17 C20 2.1(3) . . . . ?
C21 N3 C17 C20 -179.87(19) . . . . ?
C18 N3 C17 N2 -178.80(18) . . . . ?
C21 N3 C17 N2 -0.7(3) . . . . ?
C17 N3 C18 O1 176.6(2) . . . . ?
C21 N3 C18 O1 -1.6(3) . . . . ?
C17 N3 C18 N4 -4.4(3) . . . . ?
C21 N3 C18 N4 177.43(18) . . . . ?
C19 N4 C18 O1 -178.13(19) . . . . ?
C22 N4 C18 O1 -1.0(3) . . . . ?
C19 N4 C18 N3 2.9(3) . . . . ?
C22 N4 C18 N3 179.98(18) . . . . ?
N2 C17 C20 C19 -176.87(18) . . . . ?
N3 C17 C20 C19 2.2(3) . . . . ?
N2 C17 C20 C7 7.2(3) . . . . ?
N3 C17 C20 C7 -173.79(17) . . . . ?
N1 C7 C20 C17 -25.8(2) . . . . ?
C4 C7 C20 C17 97.9(2) . . . . ?
N1 C7 C20 C19 158.21(17) . . . . ?
C4 C7 C20 C19 -78.0(2) . . . . ?
C18 N4 C19 O2 -179.81(19) . . . . ?
C22 N4 C19 O2 3.1(3) . . . . ?
C18 N4 C19 C20 1.0(3) . . . . ?
C22 N4 C19 C20 -176.05(19) . . . . ?
C17 C20 C19 O2 177.29(19) . . . . ?
C7 C20 C19 O2 -6.8(3) . . . . ?
C17 C20 C19 N4 -3.6(3) . . . . ?
C7 C20 C19 N4 172.31(17) . . . . ?
C16 N1 C8 C9A 28.6(4) . . . . ?
C7 N1 C8 C9A -138.9(3) . . . . ?
C16 N1 C8 C9B -19.0(5) . . . . ?
C7 N1 C8 C9B 173.5(4) . . . . ?
N1 C8 C9A C10 -45.4(5) . . . . ?
N1 C8 C9B C10 40.0(5) . . . . ?
C14 C15 C10 C11 2.0(4) . . . . ?
C16 C15 C10 C11 -176.3(2) . . . . ?
C14 C15 C10 C9A 160.9(3) . . . . ?
C16 C15 C10 C9A -17.4(4) . . . . ?
C14 C15 C10 C9B -155.8(3) . . . . ?
C16 C15 C10 C9B 25.8(4) . . . . ?
C8 C9A C10 C15 40.9(5) . . . . ?
C8 C9A C10 C11 -161.0(3) . . . . ?
C8 C9B C10 C15 -43.6(5) . . . . ?
C8 C9B C10 C11 159.2(3) . . . . ?
C15 C10 C11 C12 -0.8(5) . . . . ?
C9A C10 C11 C12 -158.4(4) . . . . ?
C9B C10 C11 C12 155.9(4) . . . . ?
C10 C11 C12 C13 -0.8(5) . . . . ?
C11 C12 C13 C14 1.1(4) . . . . ?
C15 C14 C13 C12 0.1(4) . . . . ?
C39 N6 C38 N5 -5.3(3) . . . . ?
C39 N6 C38 C37 174.28(16) . . . . ?
C29 N5 C38 N6 -14.4(3) . . . . ?
C30 N5 C38 N6 172.2(2) . . . . ?
C29 N5 C38 C37 166.04(18) . . . . ?
C30 N5 C38 C37 -7.4(3) . . . . ?
C36 C37 C38 N6 -8.6(3) . . . . ?
C32 C37 C38 N6 168.7(2) . . . . ?
C36 C37 C38 N5 170.99(19) . . . . ?
C32 C37 C38 N5 -11.7(3) . . . . ?
C38 N6 C39 C42 9.2(3) . . . . ?
C38 N6 C39 N7 -169.49(17) . . . . ?
C40 N7 C39 C42 2.8(3) . . . . ?
C43 N7 C39 C42 178.6(2) . . . . ?
C40 N7 C39 N6 -178.44(18) . . . . ?
C43 N7 C39 N6 -2.7(3) . . . . ?
C39 N7 C40 O3 176.7(2) . . . . ?
C43 N7 C40 O3 0.8(3) . . . . ?
C39 N7 C40 N8 -4.3(3) . . . . ?
C43 N7 C40 N8 179.7(2) . . . . ?
C41 N8 C40 O3 -178.9(2) . . . . ?
C44 N8 C40 O3 -2.7(3) . . . . ?
C41 N8 C40 N7 2.1(3) . . . . ?
C44 N8 C40 N7 178.34(19) . . . . ?
C40 N8 C41 O4 -178.5(2) . . . . ?
C44 N8 C41 O4 5.4(3) . . . . ?
C40 N8 C41 C42 1.4(3) . . . . ?
C44 N8 C41 C42 -174.73(19) . . . . ?
N6 C39 C42 C41 -177.54(19) . . . . ?
N7 C39 C42 C41 1.1(3) . . . . ?
N6 C39 C42 C29 6.2(3) . . . . ?
N7 C39 C42 C29 -175.23(17) . . . . ?
O4 C41 C42 C39 176.9(2) . . . . ?
N8 C41 C42 C39 -3.0(3) . . . . ?
O4 C41 C42 C29 -6.8(3) . . . . ?
N8 C41 C42 C29 173.26(17) . . . . ?
C32 C37 C36 C35 1.2(3) . . . . ?
C38 C37 C36 C35 178.5(2) . . . . ?
C37 C36 C35 C34 0.7(4) . . . . ?
C36 C35 C34 C33 -1.5(4) . . . . ?
C35 C34 C33 C32 0.3(4) . . . . ?
C36 C37 C32 C33 -2.3(3) . . . . ?
C38 C37 C32 C33 -179.7(2) . . . . ?
C36 C37 C32 C31 175.0(2) . . . . ?
C38 C37 C32 C31 -2.3(3) . . . . ?
C34 C33 C32 C37 1.7(4) . . . . ?
C34 C33 C32 C31 -175.5(3) . . . . ?
C37 C32 C31 C30 32.9(3) . . . . ?
C33 C32 C31 C30 -149.9(3) . . . . ?
C38 N5 C30 C31 38.9(3) . . . . ?
C29 N5 C30 C31 -134.9(2) . . . . ?
C32 C31 C30 N5 -49.2(3) . . . . ?
C38 N5 C29 C42 26.5(3) . . . . ?
C30 N5 C29 C42 -159.69(19) . . . . ?
C38 N5 C29 C26 -96.8(2) . . . . ?
C30 N5 C29 C26 76.9(2) . . . . ?
C39 C42 C29 N5 -22.3(3) . . . . ?
C41 C42 C29 N5 161.32(18) . . . . ?
C39 C42 C29 C26 100.3(2) . . . . ?
C41 C42 C29 C26 -76.1(2) . . . . ?
C23 C28 C27 C26 -1.2(4) . . . . ?
C28 C27 C26 C25 1.3(3) . . . . ?
C28 C27 C26 C29 -176.5(2) . . . . ?
N5 C29 C26 C25 28.6(3) . . . . ?
C42 C29 C26 C25 -92.3(2) . . . . ?
N5 C29 C26 C27 -153.70(19) . . . . ?
C42 C29 C26 C27 85.4(2) . . . . ?
C27 C26 C25 C24 -0.6(3) . . . . ?
C29 C26 C25 C24 177.1(2) . . . . ?
C26 C25 C24 C23 -0.1(4) . . . . ?
C27 C28 C23 C24 0.5(4) . . . . ?
C25 C24 C23 C28 0.1(4) . . . . ?

_refine_diff_density_max         0.544
_refine_diff_density_min         -0.510
_refine_diff_density_rms         0.138



