# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_compound_pyrene_derivative
_database_code_depnum_ccdc_archive 'CCDC 900558'
_audit_update_record             
;
2014-10-06 deposited with the CCDC.
2015-02-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C45 H40 N4 O2'
_chemical_formula_weight         668.81

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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                   9.273(4)
_cell_length_b                   16.808(7)
_cell_length_c                   23.315(9)
_cell_angle_alpha                90
_cell_angle_beta                 100.688(15)
_cell_angle_gamma                90
_cell_volume                     3571(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    308
_cell_measurement_theta_min      2.97
_cell_measurement_theta_max      51.55

_exptl_crystal_description       block
_exptl_crystal_colour            pink
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.244
_exptl_crystal_F_000             1416
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.077
_shelx_estimated_absorpt_T_min   0.970
_shelx_estimated_absorpt_T_max   0.994
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5720
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   'SADABS (Bruker AXS Inc.)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker SMART APEX2 CCD area detector'
_diffrn_detector                 'CCD area detector'
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20045
_diffrn_reflns_av_unetI/netI     0.0747
_diffrn_reflns_av_R_equivalents  0.0788
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         1.503
_diffrn_reflns_theta_max         26.366
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             7267
_reflns_number_gt                3736
_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 SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'OLEX2 (J. Appl. Cryst., 2009, 42, 339-341)'
_computing_publication_material  'SHELXL-2013 (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)+(0.1225P)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     SHELXL
_refine_ls_extinction_coef       0.0089(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         7267
_refine_ls_number_parameters     465
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1297
_refine_ls_R_factor_gt           0.0673
_refine_ls_wR_factor_ref         0.2194
_refine_ls_wR_factor_gt          0.1798
_refine_ls_goodness_of_fit_ref   0.957
_refine_ls_restrained_S_all      0.957
_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 0.1288(2) 0.92898(10) 0.00988(6) 0.0559(5) Uani 1 1 d . . . . .
C2 C 0.1314(3) 0.93978(14) -0.04882(9) 0.0456(6) Uani 1 1 d . . . . .
C3 C 0.2132(3) 1.00485(15) -0.06095(10) 0.0519(7) Uani 1 1 d . . . . .
H3 H 0.2629 1.0356 -0.0304 0.062 Uiso 1 1 calc R U . . .
C4 C 0.2219(3) 1.02472(16) -0.11866(10) 0.0529(7) Uani 1 1 d . . . . .
C5 C 0.1482(3) 0.97473(18) -0.16253(11) 0.0653(8) Uani 1 1 d . . . . .
H5 H 0.1522 0.9853 -0.2014 0.078 Uiso 1 1 calc R U . . .
C6 C 0.0703(3) 0.91041(17) -0.14896(11) 0.0648(8) Uani 1 1 d . . . . .
H6 H 0.0216 0.8789 -0.1793 0.078 Uiso 1 1 calc R U . . .
C7 C 0.0604(3) 0.88981(15) -0.09175(10) 0.0490(6) Uani 1 1 d . . . . .
C8 C -0.0327(3) 0.82104(14) -0.07838(10) 0.0478(6) Uani 1 1 d . . . . .
C9 C -0.0144(3) 0.80787(14) -0.01275(10) 0.0483(6) Uani 1 1 d . . . . .
C10 C -0.0727(3) 0.74231(17) 0.01077(11) 0.0646(8) Uani 1 1 d . . . . .
H10 H -0.1252 0.7053 -0.0145 0.078 Uiso 1 1 calc R U . . .
C11 C -0.0563(3) 0.72966(18) 0.06984(12) 0.0710(9) Uani 1 1 d . . . . .
H11 H -0.0941 0.6836 0.0835 0.085 Uiso 1 1 calc R U . . .
C12 C 0.0176(3) 0.78583(17) 0.11026(11) 0.0606(7) Uani 1 1 d . . . . .
C13 C 0.0778(3) 0.85169(16) 0.08681(10) 0.0539(7) Uani 1 1 d . . . . .
H13 H 0.1296 0.8894 0.1117 0.065 Uiso 1 1 calc R U . . .
C14 C 0.0612(3) 0.86159(14) 0.02671(9) 0.0444(6) Uani 1 1 d . . . . .
N15 N 0.2984(3) 1.09050(15) -0.13117(10) 0.0711(7) Uani 1 1 d . . . . .
C16 C 0.3065(4) 1.1114(2) -0.19155(13) 0.0799(10) Uani 1 1 d . . . . .
H16A H 0.3357 1.1667 -0.1926 0.096 Uiso 1 1 calc R U . . .
H16B H 0.2091 1.1065 -0.2152 0.096 Uiso 1 1 calc R U . . .
C17 C 0.4119(5) 1.0611(3) -0.21898(18) 0.1177(15) Uani 1 1 d . . . . .
H17A H 0.5085 1.0643 -0.1955 0.141 Uiso 1 1 calc R U . . .
H17B H 0.4142 1.0804 -0.2575 0.141 Uiso 1 1 calc R U . . .
H17C H 0.3797 1.0067 -0.2212 0.141 Uiso 1 1 calc R U . . .
C18 C 0.3684(4) 1.14394(18) -0.08430(15) 0.0795(10) Uani 1 1 d . . . . .
H18A H 0.3042 1.1500 -0.0561 0.095 Uiso 1 1 calc R U . . .
H18B H 0.3807 1.1960 -0.1007 0.095 Uiso 1 1 calc R U . . .
C19 C 0.5153(4) 1.1142(3) -0.05343(18) 0.1054(13) Uani 1 1 d . . . . .
H19A H 0.5056 1.0607 -0.0403 0.126 Uiso 1 1 calc R U . . .
H19B H 0.5508 1.1478 -0.0205 0.126 Uiso 1 1 calc R U . . .
H19C H 0.5835 1.1153 -0.0798 0.126 Uiso 1 1 calc R U . . .
N20 N 0.0269(3) 0.77660(16) 0.16994(10) 0.0802(8) Uani 1 1 d . . . . .
C21 C -0.0166(5) 0.7017(2) 0.19378(14) 0.0957(12) Uani 1 1 d . . . . .
H21A H -0.1105 0.6852 0.1713 0.115 Uiso 1 1 calc R U . . .
H21B H -0.0293 0.7105 0.2337 0.115 Uiso 1 1 calc R U . . .
C22 C 0.0934(5) 0.6353(3) 0.19316(17) 0.1111(14) Uani 1 1 d . . . . .
H22A H 0.1116 0.6285 0.1542 0.133 Uiso 1 1 calc R U . . .
H22B H 0.0548 0.5868 0.2059 0.133 Uiso 1 1 calc R U . . .
H22C H 0.1834 0.6485 0.2189 0.133 Uiso 1 1 calc R U . . .
C23 C 0.1017(4) 0.8362(2) 0.21195(13) 0.0850(10) Uani 1 1 d . . . . .
H23A H 0.0846 0.8890 0.1952 0.102 Uiso 1 1 calc R U . . .
H23B H 0.0603 0.8345 0.2472 0.102 Uiso 1 1 calc R U . . .
C24 C 0.2578(5) 0.8219(3) 0.2267(2) 0.1221(15) Uani 1 1 d . . . . .
H24A H 0.2756 0.7740 0.2493 0.146 Uiso 1 1 calc R U . . .
H24B H 0.3046 0.8659 0.2490 0.146 Uiso 1 1 calc R U . . .
H24C H 0.2969 0.8163 0.1916 0.146 Uiso 1 1 calc R U . . .
C25 C -0.1932(3) 0.83217(15) -0.10638(9) 0.0477(6) Uani 1 1 d . . . . .
C26 C -0.2866(3) 0.89222(17) -0.09643(11) 0.0613(7) Uani 1 1 d . . . . .
H26 H -0.2535 0.9334 -0.0707 0.074 Uiso 1 1 calc R U . . .
C27 C -0.4320(4) 0.8898(2) -0.12583(13) 0.0746(9) Uani 1 1 d . . . . .
H27 H -0.4976 0.9290 -0.1191 0.090 Uiso 1 1 calc R U . . .
C28 C -0.4790(4) 0.8291(2) -0.16503(14) 0.0787(9) Uani 1 1 d . . . . .
H28 H -0.5763 0.8281 -0.1843 0.094 Uiso 1 1 calc R U . . .
C29 C -0.3852(3) 0.77032(19) -0.17614(12) 0.0690(8) Uani 1 1 d . . . . .
H29 H -0.4171 0.7305 -0.2033 0.083 Uiso 1 1 calc R U . . .
C30 C -0.2402(3) 0.77179(16) -0.14560(10) 0.0524(7) Uani 1 1 d . . . . .
C31 C -0.1201(3) 0.71532(16) -0.14719(11) 0.0563(7) Uani 1 1 d . . . . .
N32 N 0.0003(3) 0.74641(13) -0.10928(9) 0.0560(6) Uani 1 1 d . . . . .
O33 O -0.1206(2) 0.65406(12) -0.17478(9) 0.0781(6) Uani 1 1 d . . . . .
N34 N 0.1296(3) 0.70266(14) -0.10015(10) 0.0642(6) Uani 1 1 d . . . . .
C35 C 0.2345(4) 0.72241(18) -0.05934(14) 0.0716(8) Uani 1 1 d . . . . .
H35 H 0.2246 0.7667 -0.0365 0.086 Uiso 1 1 calc R U . . .
C36 C 0.3738(3) 0.67502(17) -0.04778(14) 0.0689(8) Uani 1 1 d . . . . .
C37 C 0.4359(4) 0.64760(19) -0.09370(15) 0.0758(9) Uani 1 1 d . . . . .
H37 H 0.3917 0.6605 -0.1317 0.091 Uiso 1 1 calc R U . . .
C38 C 0.5614(4) 0.6017(2) -0.08474(17) 0.0823(10) Uani 1 1 d . . . . .
H38 H 0.6021 0.5857 -0.1164 0.099 Uiso 1 1 calc R U . . .
C39 C 0.6276(4) 0.57917(19) -0.02840(18) 0.0767(9) Uani 1 1 d . . . . .
C40 C 0.7553(4) 0.5289(2) -0.0177(2) 0.0986(12) Uani 1 1 d . . . . .
H40 H 0.7983 0.5130 -0.0488 0.118 Uiso 1 1 calc R U . . .
C41 C 0.8137(5) 0.5044(2) 0.0369(3) 0.1040(13) Uani 1 1 d . . . . .
H41 H 0.8952 0.4711 0.0424 0.125 Uiso 1 1 calc R U . . .
C42 C 0.7537(4) 0.5282(2) 0.0867(2) 0.0911(11) Uani 1 1 d . . . . .
C43 C 0.8079(6) 0.5020(2) 0.1426(3) 0.1150(15) Uani 1 1 d . . . . .
H43 H 0.8865 0.4668 0.1487 0.138 Uiso 1 1 calc R U . . .
C44 C 0.7485(6) 0.5267(3) 0.1901(2) 0.1207(16) Uani 1 1 d . . . . .
H44 H 0.7890 0.5093 0.2274 0.145 Uiso 1 1 calc R U . . .
C45 C 0.6273(5) 0.5781(2) 0.1816(2) 0.1065(13) Uani 1 1 d . . . . .
H45 H 0.5872 0.5947 0.2134 0.128 Uiso 1 1 calc R U . . .
C46 C 0.5663(4) 0.6046(2) 0.12511(17) 0.0836(10) Uani 1 1 d . . . . .
C47 C 0.6284(4) 0.58056(17) 0.07755(17) 0.0769(9) Uani 1 1 d . . . . .
C48 C 0.5651(3) 0.60560(16) 0.01936(14) 0.0643(8) Uani 1 1 d . . . . .
C49 C 0.4399(4) 0.6553(2) 0.11411(16) 0.0832(10) Uani 1 1 d . . . . .
H49 H 0.3999 0.6730 0.1456 0.100 Uiso 1 1 calc R U . . .
C50 C 0.3769(4) 0.67831(19) 0.05985(15) 0.0771(9) Uani 1 1 d . . . . .
H50 H 0.2928 0.7097 0.0544 0.092 Uiso 1 1 calc R U . . .
C51 C 0.4392(3) 0.65450(16) 0.00976(14) 0.0643(8) 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
O1 C2 1.386(3) . ?
O1 C14 1.386(3) . ?
C2 C7 1.377(3) . ?
C2 C3 1.390(3) . ?
C3 C4 1.403(3) . ?
C3 H3 0.9300 . ?
C4 N15 1.374(3) . ?
C4 C5 1.400(4) . ?
C5 C6 1.370(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.398(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.509(3) . ?
C8 N32 1.506(3) . ?
C8 C25 1.522(4) . ?
C8 C9 1.524(3) . ?
C9 C14 1.383(3) . ?
C9 C10 1.385(3) . ?
C10 C11 1.374(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.417(4) . ?
C11 H11 0.9300 . ?
C12 N20 1.387(3) . ?
C12 C13 1.396(4) . ?
C13 C14 1.391(3) . ?
C13 H13 0.9300 . ?
N15 C16 1.466(4) . ?
N15 C18 1.469(4) . ?
C16 C17 1.521(5) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 C19 1.504(5) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
N20 C21 1.463(4) . ?
N20 C23 1.481(4) . ?
C21 C22 1.513(5) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 C24 1.444(5) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C25 C26 1.377(4) . ?
C25 C30 1.382(3) . ?
C26 C27 1.396(4) . ?
C26 H26 0.9300 . ?
C27 C28 1.385(4) . ?
C27 H27 0.9300 . ?
C28 C29 1.372(4) . ?
C28 H28 0.9300 . ?
C29 C30 1.400(4) . ?
C29 H29 0.9300 . ?
C30 C31 1.469(4) . ?
C31 O33 1.214(3) . ?
C31 N32 1.391(3) . ?
N32 N34 1.389(3) . ?
N34 C35 1.272(4) . ?
C35 C36 1.499(4) . ?
C35 H35 0.9300 . ?
C36 C37 1.385(4) . ?
C36 C51 1.409(4) . ?
C37 C38 1.379(4) . ?
C37 H37 0.9300 . ?
C38 C39 1.395(5) . ?
C38 H38 0.9300 . ?
C39 C48 1.419(4) . ?
C39 C40 1.438(5) . ?
C40 C41 1.352(6) . ?
C40 H40 0.9300 . ?
C41 C42 1.433(6) . ?
C41 H41 0.9300 . ?
C42 C43 1.380(6) . ?
C42 C47 1.442(5) . ?
C43 C44 1.388(6) . ?
C43 H43 0.9300 . ?
C44 C45 1.402(6) . ?
C44 H44 0.9300 . ?
C45 C46 1.406(5) . ?
C45 H45 0.9300 . ?
C46 C47 1.401(5) . ?
C46 C49 1.433(5) . ?
C47 C48 1.438(5) . ?
C48 C51 1.411(4) . ?
C49 C50 1.348(5) . ?
C49 H49 0.9300 . ?
C50 C51 1.452(4) . ?
C50 H50 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
C2 O1 C14 118.60(17) . . ?
C7 C2 O1 123.0(2) . . ?
C7 C2 C3 122.5(2) . . ?
O1 C2 C3 114.5(2) . . ?
C2 C3 C4 120.9(2) . . ?
C2 C3 H3 119.6 . . ?
C4 C3 H3 119.6 . . ?
N15 C4 C5 122.0(2) . . ?
N15 C4 C3 121.3(2) . . ?
C5 C4 C3 116.8(2) . . ?
C6 C5 C4 120.8(2) . . ?
C6 C5 H5 119.6 . . ?
C4 C5 H5 119.6 . . ?
C5 C6 C7 123.2(2) . . ?
C5 C6 H6 118.4 . . ?
C7 C6 H6 118.4 . . ?
C2 C7 C6 115.8(2) . . ?
C2 C7 C8 122.1(2) . . ?
C6 C7 C8 121.9(2) . . ?
N32 C8 C7 111.37(19) . . ?
N32 C8 C25 99.61(19) . . ?
C7 C8 C25 111.6(2) . . ?
N32 C8 C9 111.38(19) . . ?
C7 C8 C9 110.91(19) . . ?
C25 C8 C9 111.5(2) . . ?
C14 C9 C10 116.3(2) . . ?
C14 C9 C8 121.4(2) . . ?
C10 C9 C8 122.3(2) . . ?
C11 C10 C9 122.8(2) . . ?
C11 C10 H10 118.6 . . ?
C9 C10 H10 118.6 . . ?
C10 C11 C12 120.9(2) . . ?
C10 C11 H11 119.5 . . ?
C12 C11 H11 119.5 . . ?
N20 C12 C13 121.8(2) . . ?
N20 C12 C11 121.7(2) . . ?
C13 C12 C11 116.5(2) . . ?
C14 C13 C12 120.8(2) . . ?
C14 C13 H13 119.6 . . ?
C12 C13 H13 119.6 . . ?
C9 C14 O1 123.02(19) . . ?
C9 C14 C13 122.7(2) . . ?
O1 C14 C13 114.3(2) . . ?
C4 N15 C16 121.1(2) . . ?
C4 N15 C18 120.6(2) . . ?
C16 N15 C18 118.3(2) . . ?
N15 C16 C17 115.0(3) . . ?
N15 C16 H16A 108.5 . . ?
C17 C16 H16A 108.5 . . ?
N15 C16 H16B 108.5 . . ?
C17 C16 H16B 108.5 . . ?
H16A C16 H16B 107.5 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
N15 C18 C19 112.9(3) . . ?
N15 C18 H18A 109.0 . . ?
C19 C18 H18A 109.0 . . ?
N15 C18 H18B 109.0 . . ?
C19 C18 H18B 109.0 . . ?
H18A C18 H18B 107.8 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C12 N20 C21 120.5(3) . . ?
C12 N20 C23 121.5(2) . . ?
C21 N20 C23 117.4(2) . . ?
N20 C21 C22 113.4(3) . . ?
N20 C21 H21A 108.9 . . ?
C22 C21 H21A 108.9 . . ?
N20 C21 H21B 108.9 . . ?
C22 C21 H21B 108.9 . . ?
H21A C21 H21B 107.7 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C24 C23 N20 111.7(3) . . ?
C24 C23 H23A 109.3 . . ?
N20 C23 H23A 109.3 . . ?
C24 C23 H23B 109.3 . . ?
N20 C23 H23B 109.3 . . ?
H23A C23 H23B 107.9 . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C26 C25 C30 121.3(3) . . ?
C26 C25 C8 127.8(2) . . ?
C30 C25 C8 110.9(2) . . ?
C25 C26 C27 118.4(3) . . ?
C25 C26 H26 120.8 . . ?
C27 C26 H26 120.8 . . ?
C28 C27 C26 120.2(3) . . ?
C28 C27 H27 119.9 . . ?
C26 C27 H27 119.9 . . ?
C29 C28 C27 121.5(3) . . ?
C29 C28 H28 119.3 . . ?
C27 C28 H28 119.3 . . ?
C28 C29 C30 118.3(3) . . ?
C28 C29 H29 120.9 . . ?
C30 C29 H29 120.9 . . ?
C25 C30 C29 120.3(3) . . ?
C25 C30 C31 110.1(2) . . ?
C29 C30 C31 129.6(2) . . ?
O33 C31 N32 125.3(3) . . ?
O33 C31 C30 129.3(3) . . ?
N32 C31 C30 105.3(2) . . ?
N34 N32 C31 117.9(2) . . ?
N34 N32 C8 127.9(2) . . ?
C31 N32 C8 114.0(2) . . ?
C35 N34 N32 119.7(2) . . ?
N34 C35 C36 120.6(3) . . ?
N34 C35 H35 119.7 . . ?
C36 C35 H35 119.7 . . ?
C37 C36 C51 119.1(3) . . ?
C37 C36 C35 120.4(3) . . ?
C51 C36 C35 120.4(3) . . ?
C38 C37 C36 121.9(3) . . ?
C38 C37 H37 119.0 . . ?
C36 C37 H37 119.0 . . ?
C37 C38 C39 120.4(3) . . ?
C37 C38 H38 119.8 . . ?
C39 C38 H38 119.8 . . ?
C38 C39 C48 118.8(3) . . ?
C38 C39 C40 121.9(4) . . ?
C48 C39 C40 119.4(4) . . ?
C41 C40 C39 121.1(4) . . ?
C41 C40 H40 119.5 . . ?
C39 C40 H40 119.5 . . ?
C40 C41 C42 121.9(4) . . ?
C40 C41 H41 119.1 . . ?
C42 C41 H41 119.1 . . ?
C43 C42 C41 123.2(5) . . ?
C43 C42 C47 118.4(4) . . ?
C41 C42 C47 118.4(4) . . ?
C42 C43 C44 122.0(5) . . ?
C42 C43 H43 119.0 . . ?
C44 C43 H43 119.0 . . ?
C43 C44 C45 119.9(5) . . ?
C43 C44 H44 120.0 . . ?
C45 C44 H44 120.0 . . ?
C44 C45 C46 119.9(5) . . ?
C44 C45 H45 120.0 . . ?
C46 C45 H45 120.0 . . ?
C47 C46 C45 119.8(4) . . ?
C47 C46 C49 118.2(3) . . ?
C45 C46 C49 122.0(4) . . ?
C46 C47 C48 120.4(3) . . ?
C46 C47 C42 119.9(4) . . ?
C48 C47 C42 119.7(4) . . ?
C51 C48 C39 120.3(3) . . ?
C51 C48 C47 120.1(3) . . ?
C39 C48 C47 119.6(3) . . ?
C50 C49 C46 122.4(3) . . ?
C50 C49 H49 118.8 . . ?
C46 C49 H49 118.8 . . ?
C49 C50 C51 120.5(3) . . ?
C49 C50 H50 119.7 . . ?
C51 C50 H50 119.7 . . ?
C36 C51 C48 119.4(3) . . ?
C36 C51 C50 122.2(3) . . ?
C48 C51 C50 118.3(3) . . ?

_refine_diff_density_max         0.395
_refine_diff_density_min         -0.294
_refine_diff_density_rms         0.095

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_compound_RDHDNAP
_database_code_depnum_ccdc_archive 'CCDC 961580'
_audit_update_record             
;
2014-10-06 deposited with the CCDC.
2015-02-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C39 H38 N4 O2'
_chemical_formula_weight         594.73

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                   11.5411(14)
_cell_length_b                   11.5412(10)
_cell_length_c                   23.608(2)
_cell_angle_alpha                90
_cell_angle_beta                 92.592(4)
_cell_angle_gamma                90
_cell_volume                     3141.4(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    385
_cell_measurement_theta_max      52.97
_cell_measurement_theta_min      2.88

_exptl_crystal_description       block
_exptl_crystal_colour            pink
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.258
_exptl_crystal_F_000             1264
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    0.078
_shelx_estimated_absorpt_T_min   0.981
_shelx_estimated_absorpt_T_max   0.995
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6401
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   'SADABS (Bruker AXS Inc.)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker SMART APEX2 CCD area detector'
_diffrn_detector                 'CCD area detector'
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20130
_diffrn_reflns_av_unetI/netI     0.0463
_diffrn_reflns_av_R_equivalents  0.0366
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         1.931
_diffrn_reflns_theta_max         26.418
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             6437
_reflns_number_gt                4432
_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 SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'OLEX2 (J. Appl. Cryst., 2009, 42, 339-341)'
_computing_publication_material  'SHELXS-2013 (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)+(0.0528P)²+0.5227P] 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         6437
_refine_ls_number_parameters     410
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0760
_refine_ls_R_factor_gt           0.0456
_refine_ls_wR_factor_ref         0.1163
_refine_ls_wR_factor_gt          0.1027
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_restrained_S_all      1.022
_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 0.23712(10) 0.63638(9) 0.19393(5) 0.0283(3) Uani 1 1 d . . . . .
C2 C 0.11945(14) 0.65477(13) 0.19827(6) 0.0237(4) Uani 1 1 d . . . . .
C3 C 0.08284(15) 0.76689(14) 0.18627(7) 0.0270(4) Uani 1 1 d . . . . .
H3 H 0.1367 0.8223 0.1735 0.032 Uiso 1 1 calc R U . . .
C4 C -0.03288(15) 0.79939(14) 0.19279(7) 0.0278(4) Uani 1 1 d . . . . .
C5 C -0.11057(15) 0.71135(14) 0.20864(7) 0.0293(4) Uani 1 1 d . . . . .
H5 H -0.1904 0.7289 0.2119 0.035 Uiso 1 1 calc R U . . .
C6 C -0.07122(15) 0.60078(14) 0.21938(7) 0.0279(4) Uani 1 1 d . . . . .
H6 H -0.1254 0.5436 0.2299 0.034 Uiso 1 1 calc R U . . .
C7 C 0.04466(14) 0.56875(13) 0.21549(6) 0.0237(4) Uani 1 1 d . . . . .
C8 C 0.08922(14) 0.44784(13) 0.22965(6) 0.0245(4) Uani 1 1 d . . . . .
C9 C 0.20555(14) 0.42908(13) 0.20365(6) 0.0239(4) Uani 1 1 d . . . . .
C10 C 0.25285(15) 0.31984(14) 0.19555(7) 0.0292(4) Uani 1 1 d . . . . .
H10 H 0.2073 0.2535 0.2030 0.035 Uiso 1 1 calc R U . . .
C11 C 0.36321(16) 0.30413(14) 0.17710(7) 0.0307(4) Uani 1 1 d . . . . .
H11 H 0.3909 0.2278 0.1711 0.037 Uiso 1 1 calc R U . . .
C12 C 0.43583(15) 0.39946(14) 0.16693(7) 0.0274(4) Uani 1 1 d . . . . .
C13 C 0.38799(14) 0.50957(14) 0.17399(6) 0.0258(4) Uani 1 1 d . . . . .
H13 H 0.4334 0.5763 0.1671 0.031 Uiso 1 1 calc R U . . .
C14 C 0.27535(14) 0.52269(13) 0.19097(6) 0.0241(4) Uani 1 1 d . . . . .
N15 N -0.06837(13) 0.91252(12) 0.18489(7) 0.0382(4) Uani 1 1 d . . . . .
C16 C -0.18430(17) 0.95175(16) 0.19781(9) 0.0428(5) Uani 1 1 d . . . . .
H16A H -0.1775 1.0235 0.2207 0.051 Uiso 1 1 calc R U . . .
H16B H -0.2213 0.8921 0.2211 0.051 Uiso 1 1 calc R U . . .
C17 C -0.2594(2) 0.9745(3) 0.14705(11) 0.0761(8) Uani 1 1 d . . . . .
H17A H -0.2258 1.0369 0.1249 0.091 Uiso 1 1 calc R U . . .
H17B H -0.3366 0.9978 0.1585 0.091 Uiso 1 1 calc R U . . .
H17C H -0.2659 0.9041 0.1239 0.091 Uiso 1 1 calc R U . . .
C18 C 0.01151(17) 1.00175(15) 0.16792(8) 0.0396(5) Uani 1 1 d . . . . .
H18A H 0.0859 0.9919 0.1900 0.048 Uiso 1 1 calc R U . . .
H18B H -0.0205 1.0784 0.1778 0.048 Uiso 1 1 calc R U . . .
C19 C 0.03538(19) 1.00097(17) 0.10523(9) 0.0493(5) Uani 1 1 d . . . . .
H19A H 0.0709 0.9270 0.0954 0.059 Uiso 1 1 calc R U . . .
H19B H 0.0883 1.0645 0.0969 0.059 Uiso 1 1 calc R U . . .
H19C H -0.0377 1.0109 0.0829 0.059 Uiso 1 1 calc R U . . .
N20 N 0.54837(13) 0.38495(12) 0.15095(6) 0.0328(4) Uani 1 1 d . . . . .
C21 C 0.59252(17) 0.26981(16) 0.13729(8) 0.0394(5) Uani 1 1 d . . . . .
H21A H 0.5692 0.2146 0.1668 0.047 Uiso 1 1 calc R U . . .
H21B H 0.6783 0.2727 0.1387 0.047 Uiso 1 1 calc R U . . .
C22 C 0.55043(19) 0.22411(17) 0.07973(8) 0.0470(5) Uani 1 1 d . . . . .
H22A H 0.4655 0.2267 0.0767 0.056 Uiso 1 1 calc R U . . .
H22B H 0.5767 0.1440 0.0754 0.056 Uiso 1 1 calc R U . . .
H22C H 0.5819 0.2722 0.0499 0.056 Uiso 1 1 calc R U . . .
C23 C 0.61663(16) 0.48494(16) 0.13389(8) 0.0387(5) Uani 1 1 d . . . . .
H23A H 0.6996 0.4629 0.1352 0.046 Uiso 1 1 calc R U . . .
H23B H 0.6073 0.5480 0.1617 0.046 Uiso 1 1 calc R U . . .
C24 C 0.5836(2) 0.53051(17) 0.07534(8) 0.0474(5) Uani 1 1 d . . . . .
H24A H 0.5973 0.4703 0.0471 0.057 Uiso 1 1 calc R U . . .
H24B H 0.6308 0.5988 0.0675 0.057 Uiso 1 1 calc R U . . .
H24C H 0.5014 0.5519 0.0734 0.057 Uiso 1 1 calc R U . . .
C25 C 0.09729(15) 0.42918(13) 0.29374(7) 0.0256(4) Uani 1 1 d . . . . .
C26 C 0.16350(15) 0.48930(14) 0.33442(7) 0.0305(4) Uani 1 1 d . . . . .
H26 H 0.2148 0.5492 0.3240 0.037 Uiso 1 1 calc R U . . .
C27 C 0.15271(17) 0.45971(16) 0.39053(7) 0.0383(5) Uani 1 1 d . . . . .
H27 H 0.1968 0.5005 0.4190 0.046 Uiso 1 1 calc R U . . .
C28 C 0.07892(18) 0.37165(16) 0.40634(8) 0.0413(5) Uani 1 1 d . . . . .
H28 H 0.0729 0.3534 0.4453 0.050 Uiso 1 1 calc R U . . .
C29 C 0.01416(17) 0.31032(15) 0.36598(7) 0.0370(5) Uani 1 1 d . . . . .
H29 H -0.0360 0.2495 0.3764 0.044 Uiso 1 1 calc R U . . .
C30 C 0.02498(15) 0.34076(14) 0.30950(7) 0.0287(4) Uani 1 1 d . . . . .
C31 C -0.03697(15) 0.29387(14) 0.25880(7) 0.0295(4) Uani 1 1 d . . . . .
N32 N 0.00305(12) 0.35578(11) 0.21331(5) 0.0260(3) Uani 1 1 d . . . . .
O33 O -0.11009(11) 0.21747(10) 0.25612(5) 0.0385(3) Uani 1 1 d . . . . .
N34 N -0.05445(13) 0.34045(11) 0.16153(6) 0.0294(3) Uani 1 1 d . . . . .
C35 C -0.02642(15) 0.40530(14) 0.12032(7) 0.0295(4) Uani 1 1 d . . . . .
H35 H 0.0361 0.4585 0.1250 0.035 Uiso 1 1 calc R U . . .
C36 C -0.09223(15) 0.39630(15) 0.06577(7) 0.0307(4) Uani 1 1 d . . . . .
C37 C -0.12442(15) 0.50007(15) 0.03587(7) 0.0314(4) Uani 1 1 d . . . . .
C38 C -0.10072(17) 0.61223(15) 0.05772(8) 0.0363(4) Uani 1 1 d . . . . .
H38 H -0.0593 0.6204 0.0932 0.044 Uiso 1 1 calc R U . . .
C39 C -0.13656(18) 0.70903(17) 0.02847(8) 0.0439(5) Uani 1 1 d . . . . .
H39 H -0.1194 0.7837 0.0436 0.053 Uiso 1 1 calc R U . . .
C40 C -0.19872(18) 0.69866(18) -0.02398(8) 0.0462(5) Uani 1 1 d . . . . .
H40 H -0.2234 0.7664 -0.0440 0.055 Uiso 1 1 calc R U . . .
C41 C -0.22356(17) 0.59275(17) -0.04614(8) 0.0412(5) Uani 1 1 d . . . . .
H41 H -0.2654 0.5871 -0.0816 0.049 Uiso 1 1 calc R U . . .
C42 C -0.18800(16) 0.49013(17) -0.01714(7) 0.0349(4) Uani 1 1 d . . . . .
C43 C -0.21540(17) 0.37867(17) -0.03867(8) 0.0411(5) Uani 1 1 d . . . . .
H43 H -0.2561 0.3714 -0.0744 0.049 Uiso 1 1 calc R U . . .
C44 C -0.18429(17) 0.28146(18) -0.00888(8) 0.0424(5) Uani 1 1 d . . . . .
H44 H -0.2041 0.2073 -0.0238 0.051 Uiso 1 1 calc R U . . .
C45 C -0.12335(17) 0.29024(16) 0.04359(8) 0.0371(4) Uani 1 1 d . . . . .
H45 H -0.1033 0.2218 0.0641 0.045 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 C2 1.3829(19) . ?
O1 C14 1.3870(18) . ?
C2 C3 1.386(2) . ?
C2 C7 1.388(2) . ?
C3 C4 1.402(2) . ?
C3 H3 0.9500 . ?
C4 N15 1.379(2) . ?
C4 C5 1.417(2) . ?
C5 C6 1.374(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.395(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.519(2) . ?
C8 N32 1.494(2) . ?
C8 C9 1.517(2) . ?
C8 C25 1.527(2) . ?
C9 C14 1.388(2) . ?
C9 C10 1.391(2) . ?
C10 C11 1.377(2) . ?
C10 H10 0.9500 . ?
C11 C12 1.410(2) . ?
C11 H11 0.9500 . ?
C12 N20 1.379(2) . ?
C12 C13 1.399(2) . ?
C13 C14 1.386(2) . ?
C13 H13 0.9500 . ?
N15 C18 1.451(2) . ?
N15 C16 1.458(2) . ?
C16 C17 1.471(3) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 C19 1.518(3) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
N20 C23 1.464(2) . ?
N20 C21 1.464(2) . ?
C21 C22 1.517(3) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 C24 1.511(3) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 C30 1.380(2) . ?
C25 C26 1.386(2) . ?
C26 C27 1.379(2) . ?
C26 H26 0.9500 . ?
C27 C28 1.388(3) . ?
C27 H27 0.9500 . ?
C28 C29 1.379(3) . ?
C28 H28 0.9500 . ?
C29 C30 1.390(2) . ?
C29 H29 0.9500 . ?
C30 C31 1.469(2) . ?
C31 O33 1.220(2) . ?
C31 N32 1.386(2) . ?
N32 N34 1.3759(19) . ?
N34 C35 1.281(2) . ?
C35 C36 1.469(2) . ?
C35 H35 0.9500 . ?
C36 C45 1.373(2) . ?
C36 C37 1.431(2) . ?
C37 C38 1.416(2) . ?
C37 C42 1.426(2) . ?
C38 C39 1.368(3) . ?
C38 H38 0.9500 . ?
C39 C40 1.408(3) . ?
C39 H39 0.9500 . ?
C40 C41 1.355(3) . ?
C40 H40 0.9500 . ?
C41 C42 1.419(3) . ?
C41 H41 0.9500 . ?
C42 C43 1.414(3) . ?
C43 C44 1.364(3) . ?
C43 H43 0.9500 . ?
C44 C45 1.400(3) . ?
C44 H44 0.9500 . ?
C45 H45 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
C2 O1 C14 117.69(12) . . ?
O1 C2 C3 114.79(14) . . ?
O1 C2 C7 122.52(14) . . ?
C3 C2 C7 122.64(15) . . ?
C2 C3 C4 120.67(15) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 H3 119.7 . . ?
N15 C4 C3 121.14(15) . . ?
N15 C4 C5 121.82(15) . . ?
C3 C4 C5 117.03(14) . . ?
C6 C5 C4 120.46(16) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
C5 C6 C7 122.95(15) . . ?
C5 C6 H6 118.5 . . ?
C7 C6 H6 118.5 . . ?
C2 C7 C6 116.14(14) . . ?
C2 C7 C8 120.83(14) . . ?
C6 C7 C8 123.03(14) . . ?
N32 C8 C9 112.65(12) . . ?
N32 C8 C7 112.44(13) . . ?
C9 C8 C7 109.82(12) . . ?
N32 C8 C25 99.52(12) . . ?
C9 C8 C25 111.43(14) . . ?
C7 C8 C25 110.64(12) . . ?
C14 C9 C10 116.15(15) . . ?
C14 C9 C8 120.60(14) . . ?
C10 C9 C8 123.04(14) . . ?
C11 C10 C9 122.51(15) . . ?
C11 C10 H10 118.7 . . ?
C9 C10 H10 118.7 . . ?
C10 C11 C12 121.11(15) . . ?
C10 C11 H11 119.4 . . ?
C12 C11 H11 119.4 . . ?
N20 C12 C13 121.65(15) . . ?
N20 C12 C11 121.75(15) . . ?
C13 C12 C11 116.60(15) . . ?
C14 C13 C12 120.95(15) . . ?
C14 C13 H13 119.5 . . ?
C12 C13 H13 119.5 . . ?
C13 C14 O1 115.00(14) . . ?
C13 C14 C9 122.57(14) . . ?
O1 C14 C9 122.43(14) . . ?
C4 N15 C18 121.40(15) . . ?
C4 N15 C16 122.40(14) . . ?
C18 N15 C16 115.98(14) . . ?
N15 C16 C17 113.45(17) . . ?
N15 C16 H16A 108.9 . . ?
C17 C16 H16A 108.9 . . ?
N15 C16 H16B 108.9 . . ?
C17 C16 H16B 108.9 . . ?
H16A C16 H16B 107.7 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
N15 C18 C19 114.26(16) . . ?
N15 C18 H18A 108.7 . . ?
C19 C18 H18A 108.7 . . ?
N15 C18 H18B 108.7 . . ?
C19 C18 H18B 108.7 . . ?
H18A C18 H18B 107.6 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C12 N20 C23 120.32(14) . . ?
C12 N20 C21 120.79(15) . . ?
C23 N20 C21 117.24(14) . . ?
N20 C21 C22 114.34(16) . . ?
N20 C21 H21A 108.7 . . ?
C22 C21 H21A 108.7 . . ?
N20 C21 H21B 108.7 . . ?
C22 C21 H21B 108.7 . . ?
H21A C21 H21B 107.6 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
N20 C23 C24 114.16(16) . . ?
N20 C23 H23A 108.7 . . ?
C24 C23 H23A 108.7 . . ?
N20 C23 H23B 108.7 . . ?
C24 C23 H23B 108.7 . . ?
H23A C23 H23B 107.6 . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C30 C25 C26 120.30(15) . . ?
C30 C25 C8 111.16(15) . . ?
C26 C25 C8 128.53(15) . . ?
C27 C26 C25 118.07(17) . . ?
C27 C26 H26 121.0 . . ?
C25 C26 H26 121.0 . . ?
C26 C27 C28 121.52(18) . . ?
C26 C27 H27 119.2 . . ?
C28 C27 H27 119.2 . . ?
C29 C28 C27 120.65(16) . . ?
C29 C28 H28 119.7 . . ?
C27 C28 H28 119.7 . . ?
C28 C29 C30 117.62(17) . . ?
C28 C29 H29 121.2 . . ?
C30 C29 H29 121.2 . . ?
C25 C30 C29 121.81(17) . . ?
C25 C30 C31 109.30(14) . . ?
C29 C30 C31 128.82(16) . . ?
O33 C31 N32 125.89(16) . . ?
O33 C31 C30 128.19(15) . . ?
N32 C31 C30 105.92(14) . . ?
N34 N32 C31 117.25(14) . . ?
N34 N32 C8 127.55(12) . . ?
C31 N32 C8 114.07(13) . . ?
C35 N34 N32 118.14(14) . . ?
N34 C35 C36 119.10(16) . . ?
N34 C35 H35 120.4 . . ?
C36 C35 H35 120.4 . . ?
C45 C36 C37 120.05(17) . . ?
C45 C36 C35 120.89(16) . . ?
C37 C36 C35 119.06(15) . . ?
C38 C37 C42 118.46(16) . . ?
C38 C37 C36 122.96(16) . . ?
C42 C37 C36 118.51(16) . . ?
C39 C38 C37 120.93(18) . . ?
C39 C38 H38 119.5 . . ?
C37 C38 H38 119.5 . . ?
C38 C39 C40 120.34(19) . . ?
C38 C39 H39 119.8 . . ?
C40 C39 H39 119.8 . . ?
C41 C40 C39 120.45(19) . . ?
C41 C40 H40 119.8 . . ?
C39 C40 H40 119.8 . . ?
C40 C41 C42 120.99(18) . . ?
C40 C41 H41 119.5 . . ?
C42 C41 H41 119.5 . . ?
C43 C42 C41 122.05(17) . . ?
C43 C42 C37 119.12(17) . . ?
C41 C42 C37 118.82(17) . . ?
C44 C43 C42 120.91(18) . . ?
C44 C43 H43 119.5 . . ?
C42 C43 H43 119.5 . . ?
C43 C44 C45 120.45(18) . . ?
C43 C44 H44 119.8 . . ?
C45 C44 H44 119.8 . . ?
C36 C45 C44 120.94(18) . . ?
C36 C45 H45 119.5 . . ?
C44 C45 H45 119.5 . . ?

_refine_diff_density_max         0.223
_refine_diff_density_min         -0.200
_refine_diff_density_rms         0.039

_shelxl_version_number           2013-4

