# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1548639'
_audit_update_record             
;
2017-05-08 deposited with the CCDC.
2017-08-04 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_THETM01_shelx               
;
PROBLEM: The value of sine(theta_max)/wavelength is less than 0.550
RESPONSE: The crystal diffracted weakly, so no significant reflections were 
observed at a resolution less than 1.00 A. In order to not use predominantly
noise the data was cut at that resolution. 
;
_vrf_REFNR01_shelx               
;
PROBLEM: Ratio of reflections to parameters is < 8 for a
RESPONSE: The crystal diffracted weakly, so no significant reflections were 
observed at a resolution less than 1.00 A. In order to not use predominantly
noise the data was cut at that resolution. 
;
_vrf_PLAT088_shelx               
;
PROBLEM: Poor Data / Parameter Ratio .................... 7.46 Note
RESPONSE: The crystal diffracted weakly, so no significant reflections were 
observed at a resolution less than 1.00 A. In order to not use predominantly
noise the data was cut at that resolution. 
;
_vrf_PLAT910_shelx               
;
PROBLEM: Missing # of FCF Reflection(s) Below Theta(Min) 11 Note
RESPONSE: The crystal diffracted weakly, so no significant reflections were 
observed at a resolution less than 1.00 A. In order to not use predominantly
noise the data was cut at that resolution. 
;
# end Validation Reply Form

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H16 N2 O'
_chemical_formula_weight         312.36

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/n'
_space_group_name_Hall           '-P 2yn'

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

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

_cell_length_a                   9.933(2)
_cell_length_b                   29.454(6)
_cell_length_c                   11.470(2)
_cell_angle_alpha                90
_cell_angle_beta                 112.40(3)
_cell_angle_gamma                90
_cell_volume                     3102.5(12)
_cell_formula_units_Z            8
_cell_measurement_temperature    170(2)
_cell_measurement_reflns_used    54188
_cell_measurement_theta_min      6.2
_cell_measurement_theta_max      54.2

_exptl_crystal_description       stick
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.337
_exptl_crystal_F_000             1312
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.292
_exptl_crystal_size_mid          0.081
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    0.083
_shelx_estimated_absorpt_T_min   0.976
_shelx_estimated_absorpt_T_max   0.995
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      170(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'STOE IPDS2T'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 6.67
_diffrn_reflns_number            10622
_diffrn_reflns_av_unetI/netI     0.1471
_diffrn_reflns_av_R_equivalents  0.1280
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         3.109
_diffrn_reflns_theta_max         20.818
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.576
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.576
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.576
_reflns_number_total             3231
_reflns_number_gt                1351
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'X-Area by STOE & Cie GmbH 2010'
_computing_cell_refinement       'X-Area by STOE & Cie GmbH 2010'
_computing_data_reduction        'X-Area by STOE & Cie GmbH 2010'
_computing_structure_solution    'SHELXT-2014 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'XP Version 5.1 by Bruker AXS 1998'
_computing_publication_material  'CIFTAB (Sheldrick, 2013)'

_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)+(0.0269P)²] 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         3231
_refine_ls_number_parameters     433
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1464
_refine_ls_R_factor_gt           0.0448
_refine_ls_wR_factor_ref         0.0960
_refine_ls_wR_factor_gt          0.0723
_refine_ls_goodness_of_fit_ref   0.794
_refine_ls_restrained_S_all      0.794
_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 0.5941(7) 0.0924(2) 0.0453(5) 0.0238(15) Uani 1 1 d . . . . .
C2 C 0.6877(7) 0.1173(2) 0.2646(6) 0.0301(17) Uani 1 1 d . . . . .
C3 C 0.8017(6) 0.0836(2) 0.2850(6) 0.0248(16) Uani 1 1 d . . . . .
C4 C 0.9124(7) 0.0787(2) 0.4027(6) 0.0329(17) Uani 1 1 d . . . . .
H4 H 0.9152 0.0975 0.4710 0.039 Uiso 1 1 calc R U . . .
C5 C 1.0177(7) 0.0465(2) 0.4198(6) 0.0369(17) Uani 1 1 d . . . . .
H5 H 1.0952 0.0434 0.4996 0.044 Uiso 1 1 calc R U . . .
C6 C 1.0115(7) 0.0183(2) 0.3207(6) 0.0350(17) Uani 1 1 d . . . . .
H6 H 1.0833 -0.0046 0.3346 0.042 Uiso 1 1 calc R U . . .
C7 C 0.9039(7) 0.0230(2) 0.2036(6) 0.0309(17) Uani 1 1 d . . . . .
H7 H 0.9018 0.0039 0.1362 0.037 Uiso 1 1 calc R U . . .
C8 C 0.7977(7) 0.0560(2) 0.1846(5) 0.0270(16) Uani 1 1 d . . . . .
C9 C 0.4889(7) 0.1002(2) -0.0860(5) 0.0271(16) Uani 1 1 d . . . . .
C10 C 0.3494(7) 0.0825(2) -0.1310(6) 0.0362(17) Uani 1 1 d . . . . .
H10 H 0.3171 0.0648 -0.0773 0.043 Uiso 1 1 calc R U . . .
C11 C 0.2577(7) 0.0905(2) -0.2540(6) 0.0408(18) Uani 1 1 d . . . . .
H11 H 0.1613 0.0788 -0.2843 0.049 Uiso 1 1 calc R U . . .
C12 C 0.3034(8) 0.1152(2) -0.3336(6) 0.0397(19) Uani 1 1 d . . . . .
H12 H 0.2388 0.1206 -0.4181 0.048 Uiso 1 1 calc R U . . .
C13 C 0.4439(7) 0.1320(2) -0.2904(5) 0.0384(17) Uani 1 1 d . . . . .
H13 H 0.4766 0.1486 -0.3456 0.046 Uiso 1 1 calc R U . . .
C14 C 0.5368(6) 0.1247(2) -0.1664(5) 0.0333(16) Uani 1 1 d . . . . .
H14 H 0.6333 0.1363 -0.1364 0.040 Uiso 1 1 calc R U . . .
C15 C 0.4634(6) 0.1532(2) 0.1159(6) 0.0291(16) Uani 1 1 d . . . . .
H15A H 0.4435 0.1569 0.1936 0.035 Uiso 1 1 calc R U . . .
H15B H 0.3746 0.1405 0.0501 0.035 Uiso 1 1 calc R U . . .
C16 C 0.4938(6) 0.1992(2) 0.0737(6) 0.0287(16) Uani 1 1 d . . . . .
C17 C 0.4293(6) 0.21171(19) -0.0514(5) 0.0340(15) Uani 1 1 d . . . . .
H17 H 0.3669 0.1910 -0.1113 0.041 Uiso 1 1 calc R U . . .
C18 C 0.4549(6) 0.2541(2) -0.0901(6) 0.0373(16) Uani 1 1 d . . . . .
H18 H 0.4099 0.2624 -0.1764 0.045 Uiso 1 1 calc R U . . .
C19 C 0.5446(7) 0.2844(2) -0.0051(6) 0.0372(17) Uani 1 1 d . . . . .
H19 H 0.5631 0.3133 -0.0326 0.045 Uiso 1 1 calc R U . . .
C20 C 0.6079(6) 0.2727(2) 0.1208(6) 0.0388(16) Uani 1 1 d . . . . .
H20 H 0.6687 0.2938 0.1801 0.047 Uiso 1 1 calc R U . . .
C21 C 0.5833(6) 0.2303(2) 0.1609(5) 0.0364(16) Uani 1 1 d . . . . .
H21 H 0.6271 0.2224 0.2476 0.044 Uiso 1 1 calc R U . . .
C22 C 0.0933(7) 0.0907(2) 0.0510(6) 0.0266(16) Uani 1 1 d . . . . .
C23 C 0.2080(7) 0.1132(2) 0.2701(6) 0.0278(17) Uani 1 1 d . . . . .
C24 C 0.3137(7) 0.07806(19) 0.2813(6) 0.0254(16) Uani 1 1 d . . . . .
C25 C 0.4327(7) 0.0714(2) 0.3943(6) 0.0337(17) Uani 1 1 d . . . . .
H25 H 0.4445 0.0897 0.4659 0.040 Uiso 1 1 calc R U . . .
C26 C 0.5322(7) 0.0383(2) 0.4007(6) 0.0340(17) Uani 1 1 d . . . . .
H26 H 0.6136 0.0337 0.4772 0.041 Uiso 1 1 calc R U . . .
C27 C 0.5151(7) 0.0116(2) 0.2965(6) 0.0328(17) Uani 1 1 d . . . . .
H27 H 0.5850 -0.0112 0.3022 0.039 Uiso 1 1 calc R U . . .
C28 C 0.3973(7) 0.0178(2) 0.1844(6) 0.0322(17) Uani 1 1 d . . . . .
H28 H 0.3856 -0.0008 0.1134 0.039 Uiso 1 1 calc R U . . .
C29 C 0.2955(6) 0.0516(2) 0.1764(5) 0.0244(16) Uani 1 1 d . . . . .
C30 C -0.0195(7) 0.0999(2) -0.0794(5) 0.0261(16) Uani 1 1 d . . . . .
C31 C -0.0066(6) 0.13811(19) -0.1439(5) 0.0338(16) Uani 1 1 d . . . . .
H31 H 0.0659 0.1602 -0.1031 0.041 Uiso 1 1 calc R U . . .
C32 C -0.1000(7) 0.1442(2) -0.2684(6) 0.0413(17) Uani 1 1 d . . . . .
H32 H -0.0908 0.1702 -0.3138 0.050 Uiso 1 1 calc R U . . .
C33 C -0.2067(7) 0.1121(2) -0.3262(6) 0.0380(19) Uani 1 1 d . . . . .
H33 H -0.2711 0.1162 -0.4114 0.046 Uiso 1 1 calc R U . . .
C34 C -0.2197(7) 0.0745(2) -0.2605(6) 0.0404(18) Uani 1 1 d . . . . .
H34 H -0.2937 0.0528 -0.3004 0.048 Uiso 1 1 calc R U . . .
C35 C -0.1256(6) 0.0680(2) -0.1364(5) 0.0314(16) Uani 1 1 d . . . . .
H35 H -0.1341 0.0418 -0.0913 0.038 Uiso 1 1 calc R U . . .
C36 C -0.0186(6) 0.15149(19) 0.1359(6) 0.0284(16) Uani 1 1 d . . . . .
H36A H -0.0265 0.1554 0.2188 0.034 Uiso 1 1 calc R U . . .
H36B H -0.1120 0.1387 0.0772 0.034 Uiso 1 1 calc R U . . .
C37 C 0.0015(7) 0.1975(2) 0.0881(5) 0.0277(15) Uani 1 1 d . . . . .
C38 C -0.1206(7) 0.2224(2) 0.0173(5) 0.0392(16) Uani 1 1 d . . . . .
H38 H -0.2151 0.2107 0.0014 0.047 Uiso 1 1 calc R U . . .
C39 C -0.1049(7) 0.2646(2) -0.0303(6) 0.0463(18) Uani 1 1 d . . . . .
H39 H -0.1891 0.2817 -0.0773 0.056 Uiso 1 1 calc R U . . .
C40 C 0.0305(9) 0.2818(2) -0.0103(6) 0.0447(19) Uani 1 1 d . . . . .
H40 H 0.0404 0.3101 -0.0456 0.054 Uiso 1 1 calc R U . . .
C41 C 0.1527(7) 0.2570(2) 0.0621(6) 0.0453(18) Uani 1 1 d . . . . .
H41 H 0.2472 0.2687 0.0778 0.054 Uiso 1 1 calc R U . . .
C42 C 0.1372(6) 0.2154(2) 0.1116(5) 0.0383(16) Uani 1 1 d . . . . .
H42 H 0.2215 0.1990 0.1624 0.046 Uiso 1 1 calc R U . . .
N1 N 0.6922(5) 0.06140(17) 0.0634(4) 0.0283(13) Uani 1 1 d . . . . .
N2 N 0.5861(5) 0.11970(16) 0.1415(4) 0.0241(12) Uani 1 1 d . . . . .
O1 O 0.6805(5) 0.14235(15) 0.3473(4) 0.0415(12) Uani 1 1 d . . . . .
N4 N 0.1811(5) 0.05751(18) 0.0602(4) 0.0296(13) Uani 1 1 d . . . . .
N5 N 0.0973(5) 0.11856(16) 0.1501(4) 0.0264(13) Uani 1 1 d . . . . .
O2 O 0.2099(4) 0.13834(14) 0.3560(4) 0.0375(11) 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 N1 1.294(7) . ?
C1 N2 1.392(7) . ?
C1 C9 1.487(8) . ?
C2 O1 1.226(7) . ?
C2 N2 1.389(8) . ?
C2 C3 1.456(8) . ?
C3 C4 1.387(9) . ?
C3 C8 1.397(8) . ?
C4 C5 1.369(8) . ?
C4 H4 0.9500 . ?
C5 C6 1.389(8) . ?
C5 H5 0.9500 . ?
C6 C7 1.368(9) . ?
C6 H6 0.9500 . ?
C7 C8 1.390(8) . ?
C7 H7 0.9500 . ?
C8 N1 1.396(7) . ?
C9 C10 1.384(8) . ?
C9 C14 1.390(8) . ?
C10 C11 1.378(8) . ?
C10 H10 0.9500 . ?
C11 C12 1.373(8) . ?
C11 H11 0.9500 . ?
C12 C13 1.383(8) . ?
C12 H12 0.9500 . ?
C13 C14 1.386(8) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C15 N2 1.507(7) . ?
C15 C16 1.507(8) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.380(7) . ?
C16 C21 1.398(8) . ?
C17 C18 1.381(7) . ?
C17 H17 0.9500 . ?
C18 C19 1.370(8) . ?
C18 H18 0.9500 . ?
C19 C20 1.380(7) . ?
C19 H19 0.9500 . ?
C20 C21 1.384(7) . ?
C20 H20 0.9500 . ?
C21 H21 0.9500 . ?
C22 N4 1.288(7) . ?
C22 N5 1.390(7) . ?
C22 C30 1.513(9) . ?
C23 O2 1.227(7) . ?
C23 N5 1.405(8) . ?
C23 C24 1.445(8) . ?
C24 C29 1.387(8) . ?
C24 C25 1.396(9) . ?
C25 C26 1.371(8) . ?
C25 H25 0.9500 . ?
C26 C27 1.387(8) . ?
C26 H26 0.9500 . ?
C27 C28 1.382(9) . ?
C27 H27 0.9500 . ?
C28 C29 1.397(8) . ?
C28 H28 0.9500 . ?
C29 N4 1.393(7) . ?
C30 C35 1.378(8) . ?
C30 C31 1.379(8) . ?
C31 C32 1.387(8) . ?
C31 H31 0.9500 . ?
C32 C33 1.386(8) . ?
C32 H32 0.9500 . ?
C33 C34 1.374(8) . ?
C33 H33 0.9500 . ?
C34 C35 1.386(8) . ?
C34 H34 0.9500 . ?
C35 H35 0.9500 . ?
C36 N5 1.467(7) . ?
C36 C37 1.503(8) . ?
C36 H36A 0.9900 . ?
C36 H36B 0.9900 . ?
C37 C42 1.376(7) . ?
C37 C38 1.386(8) . ?
C38 C39 1.389(8) . ?
C38 H38 0.9500 . ?
C39 C40 1.372(8) . ?
C39 H39 0.9500 . ?
C40 C41 1.387(8) . ?
C40 H40 0.9500 . ?
C41 C42 1.383(8) . ?
C41 H41 0.9500 . ?
C42 H42 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 N2 123.2(5) . . ?
N1 C1 C9 117.8(5) . . ?
N2 C1 C9 118.9(6) . . ?
O1 C2 N2 121.4(6) . . ?
O1 C2 C3 123.9(6) . . ?
N2 C2 C3 114.7(6) . . ?
C4 C3 C8 120.3(6) . . ?
C4 C3 C2 120.5(6) . . ?
C8 C3 C2 119.2(6) . . ?
C5 C4 C3 119.4(6) . . ?
C5 C4 H4 120.3 . . ?
C3 C4 H4 120.3 . . ?
C4 C5 C6 120.3(6) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C7 C6 C5 121.1(6) . . ?
C7 C6 H6 119.4 . . ?
C5 C6 H6 119.4 . . ?
C6 C7 C8 119.1(6) . . ?
C6 C7 H7 120.4 . . ?
C8 C7 H7 120.4 . . ?
C7 C8 N1 118.2(5) . . ?
C7 C8 C3 119.8(5) . . ?
N1 C8 C3 121.9(6) . . ?
C10 C9 C14 119.7(5) . . ?
C10 C9 C1 122.5(6) . . ?
C14 C9 C1 117.7(6) . . ?
C11 C10 C9 119.7(6) . . ?
C11 C10 H10 120.2 . . ?
C9 C10 H10 120.2 . . ?
C12 C11 C10 121.0(6) . . ?
C12 C11 H11 119.5 . . ?
C10 C11 H11 119.5 . . ?
C11 C12 C13 119.8(6) . . ?
C11 C12 H12 120.1 . . ?
C13 C12 H12 120.1 . . ?
C12 C13 C14 119.9(6) . . ?
C12 C13 H13 120.1 . . ?
C14 C13 H13 120.1 . . ?
C13 C14 C9 120.0(6) . . ?
C13 C14 H14 120.0 . . ?
C9 C14 H14 120.0 . . ?
N2 C15 C16 113.8(5) . . ?
N2 C15 H15A 108.8 . . ?
C16 C15 H15A 108.8 . . ?
N2 C15 H15B 108.8 . . ?
C16 C15 H15B 108.8 . . ?
H15A C15 H15B 107.7 . . ?
C17 C16 C21 119.0(5) . . ?
C17 C16 C15 120.3(5) . . ?
C21 C16 C15 120.6(5) . . ?
C16 C17 C18 120.5(6) . . ?
C16 C17 H17 119.8 . . ?
C18 C17 H17 119.8 . . ?
C19 C18 C17 120.6(6) . . ?
C19 C18 H18 119.7 . . ?
C17 C18 H18 119.7 . . ?
C18 C19 C20 119.7(6) . . ?
C18 C19 H19 120.2 . . ?
C20 C19 H19 120.2 . . ?
C19 C20 C21 120.3(6) . . ?
C19 C20 H20 119.8 . . ?
C21 C20 H20 119.8 . . ?
C20 C21 C16 119.9(5) . . ?
C20 C21 H21 120.1 . . ?
C16 C21 H21 120.1 . . ?
N4 C22 N5 125.0(5) . . ?
N4 C22 C30 116.2(5) . . ?
N5 C22 C30 118.8(5) . . ?
O2 C23 N5 119.1(6) . . ?
O2 C23 C24 124.9(6) . . ?
N5 C23 C24 116.0(5) . . ?
C29 C24 C25 120.8(6) . . ?
C29 C24 C23 118.4(6) . . ?
C25 C24 C23 120.8(6) . . ?
C26 C25 C24 119.2(6) . . ?
C26 C25 H25 120.4 . . ?
C24 C25 H25 120.4 . . ?
C25 C26 C27 120.6(6) . . ?
C25 C26 H26 119.7 . . ?
C27 C26 H26 119.7 . . ?
C28 C27 C26 120.6(6) . . ?
C28 C27 H27 119.7 . . ?
C26 C27 H27 119.7 . . ?
C27 C28 C29 119.4(6) . . ?
C27 C28 H28 120.3 . . ?
C29 C28 H28 120.3 . . ?
C24 C29 N4 123.2(6) . . ?
C24 C29 C28 119.5(6) . . ?
N4 C29 C28 117.3(5) . . ?
C35 C30 C31 120.9(6) . . ?
C35 C30 C22 119.4(5) . . ?
C31 C30 C22 119.4(6) . . ?
C30 C31 C32 119.7(6) . . ?
C30 C31 H31 120.1 . . ?
C32 C31 H31 120.1 . . ?
C33 C32 C31 119.6(6) . . ?
C33 C32 H32 120.2 . . ?
C31 C32 H32 120.2 . . ?
C34 C33 C32 120.2(6) . . ?
C34 C33 H33 119.9 . . ?
C32 C33 H33 119.9 . . ?
C33 C34 C35 120.5(7) . . ?
C33 C34 H34 119.8 . . ?
C35 C34 H34 119.8 . . ?
C30 C35 C34 119.2(6) . . ?
C30 C35 H35 120.4 . . ?
C34 C35 H35 120.4 . . ?
N5 C36 C37 115.4(5) . . ?
N5 C36 H36A 108.4 . . ?
C37 C36 H36A 108.4 . . ?
N5 C36 H36B 108.4 . . ?
C37 C36 H36B 108.4 . . ?
H36A C36 H36B 107.5 . . ?
C42 C37 C38 119.0(5) . . ?
C42 C37 C36 122.1(6) . . ?
C38 C37 C36 118.9(5) . . ?
C37 C38 C39 120.0(6) . . ?
C37 C38 H38 120.0 . . ?
C39 C38 H38 120.0 . . ?
C40 C39 C38 121.0(6) . . ?
C40 C39 H39 119.5 . . ?
C38 C39 H39 119.5 . . ?
C39 C40 C41 119.0(6) . . ?
C39 C40 H40 120.5 . . ?
C41 C40 H40 120.5 . . ?
C42 C41 C40 120.1(6) . . ?
C42 C41 H41 119.9 . . ?
C40 C41 H41 119.9 . . ?
C37 C42 C41 120.9(6) . . ?
C37 C42 H42 119.5 . . ?
C41 C42 H42 119.5 . . ?
C1 N1 C8 118.3(5) . . ?
C2 N2 C1 122.5(5) . . ?
C2 N2 C15 116.9(5) . . ?
C1 N2 C15 120.6(5) . . ?
C22 N4 C29 117.0(5) . . ?
C22 N5 C23 120.2(5) . . ?
C22 N5 C36 121.5(5) . . ?
C23 N5 C36 118.1(5) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C2 C3 C4 -1.1(10) . . . . ?
N2 C2 C3 C4 178.1(5) . . . . ?
O1 C2 C3 C8 178.4(6) . . . . ?
N2 C2 C3 C8 -2.4(8) . . . . ?
C8 C3 C4 C5 0.0(9) . . . . ?
C2 C3 C4 C5 179.5(5) . . . . ?
C3 C4 C5 C6 -1.5(9) . . . . ?
C4 C5 C6 C7 2.2(10) . . . . ?
C5 C6 C7 C8 -1.2(10) . . . . ?
C6 C7 C8 N1 177.5(6) . . . . ?
C6 C7 C8 C3 -0.4(9) . . . . ?
C4 C3 C8 C7 1.0(9) . . . . ?
C2 C3 C8 C7 -178.5(6) . . . . ?
C4 C3 C8 N1 -176.8(6) . . . . ?
C2 C3 C8 N1 3.7(9) . . . . ?
N1 C1 C9 C10 99.9(7) . . . . ?
N2 C1 C9 C10 -82.4(8) . . . . ?
N1 C1 C9 C14 -77.3(7) . . . . ?
N2 C1 C9 C14 100.4(7) . . . . ?
C14 C9 C10 C11 -2.2(9) . . . . ?
C1 C9 C10 C11 -179.3(6) . . . . ?
C9 C10 C11 C12 1.2(10) . . . . ?
C10 C11 C12 C13 0.4(10) . . . . ?
C11 C12 C13 C14 -1.2(9) . . . . ?
C12 C13 C14 C9 0.2(9) . . . . ?
C10 C9 C14 C13 1.4(9) . . . . ?
C1 C9 C14 C13 178.7(6) . . . . ?
N2 C15 C16 C17 104.3(6) . . . . ?
N2 C15 C16 C21 -78.1(7) . . . . ?
C21 C16 C17 C18 1.2(9) . . . . ?
C15 C16 C17 C18 178.8(5) . . . . ?
C16 C17 C18 C19 0.0(9) . . . . ?
C17 C18 C19 C20 -1.2(9) . . . . ?
C18 C19 C20 C21 1.2(9) . . . . ?
C19 C20 C21 C16 0.0(9) . . . . ?
C17 C16 C21 C20 -1.2(8) . . . . ?
C15 C16 C21 C20 -178.8(5) . . . . ?
O2 C23 C24 C29 178.5(6) . . . . ?
N5 C23 C24 C29 -2.3(8) . . . . ?
O2 C23 C24 C25 -2.7(10) . . . . ?
N5 C23 C24 C25 176.5(6) . . . . ?
C29 C24 C25 C26 0.1(9) . . . . ?
C23 C24 C25 C26 -178.7(5) . . . . ?
C24 C25 C26 C27 -0.2(9) . . . . ?
C25 C26 C27 C28 -0.1(9) . . . . ?
C26 C27 C28 C29 0.5(10) . . . . ?
C25 C24 C29 N4 -178.2(6) . . . . ?
C23 C24 C29 N4 0.6(9) . . . . ?
C25 C24 C29 C28 0.3(9) . . . . ?
C23 C24 C29 C28 179.1(6) . . . . ?
C27 C28 C29 C24 -0.6(9) . . . . ?
C27 C28 C29 N4 178.0(5) . . . . ?
N4 C22 C30 C35 65.4(8) . . . . ?
N5 C22 C30 C35 -115.9(6) . . . . ?
N4 C22 C30 C31 -108.5(7) . . . . ?
N5 C22 C30 C31 70.2(8) . . . . ?
C35 C30 C31 C32 -1.0(9) . . . . ?
C22 C30 C31 C32 172.9(5) . . . . ?
C30 C31 C32 C33 0.9(9) . . . . ?
C31 C32 C33 C34 -0.1(9) . . . . ?
C32 C33 C34 C35 -0.6(10) . . . . ?
C31 C30 C35 C34 0.2(9) . . . . ?
C22 C30 C35 C34 -173.6(6) . . . . ?
C33 C34 C35 C30 0.6(9) . . . . ?
N5 C36 C37 C42 -29.7(8) . . . . ?
N5 C36 C37 C38 149.8(5) . . . . ?
C42 C37 C38 C39 1.0(9) . . . . ?
C36 C37 C38 C39 -178.6(5) . . . . ?
C37 C38 C39 C40 1.2(9) . . . . ?
C38 C39 C40 C41 -2.1(10) . . . . ?
C39 C40 C41 C42 0.9(9) . . . . ?
C38 C37 C42 C41 -2.2(9) . . . . ?
C36 C37 C42 C41 177.4(5) . . . . ?
C40 C41 C42 C37 1.2(9) . . . . ?
N2 C1 N1 C8 -2.1(9) . . . . ?
C9 C1 N1 C8 175.6(5) . . . . ?
C7 C8 N1 C1 -179.3(5) . . . . ?
C3 C8 N1 C1 -1.4(9) . . . . ?
O1 C2 N2 C1 178.3(5) . . . . ?
C3 C2 N2 C1 -0.9(8) . . . . ?
O1 C2 N2 C15 -2.4(9) . . . . ?
C3 C2 N2 C15 178.4(5) . . . . ?
N1 C1 N2 C2 3.3(9) . . . . ?
C9 C1 N2 C2 -174.3(6) . . . . ?
N1 C1 N2 C15 -176.0(5) . . . . ?
C9 C1 N2 C15 6.4(8) . . . . ?
C16 C15 N2 C2 92.3(6) . . . . ?
C16 C15 N2 C1 -88.4(6) . . . . ?
N5 C22 N4 C29 -5.4(9) . . . . ?
C30 C22 N4 C29 173.2(5) . . . . ?
C24 C29 N4 C22 3.1(9) . . . . ?
C28 C29 N4 C22 -175.4(5) . . . . ?
N4 C22 N5 C23 3.7(9) . . . . ?
C30 C22 N5 C23 -174.8(5) . . . . ?
N4 C22 N5 C36 -171.3(5) . . . . ?
C30 C22 N5 C36 10.1(8) . . . . ?
O2 C23 N5 C22 179.7(5) . . . . ?
C24 C23 N5 C22 0.4(8) . . . . ?
O2 C23 N5 C36 -5.2(9) . . . . ?
C24 C23 N5 C36 175.6(5) . . . . ?
C37 C36 N5 C22 -88.2(7) . . . . ?
C37 C36 N5 C23 96.7(7) . . . . ?

_refine_diff_density_max         0.159
_refine_diff_density_min         -0.202
_refine_diff_density_rms         0.041

_shelxl_version_number           2013-3

