# Electronic Supplementary Material (ESI) for Chemical Communications.
# 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_ike438
_database_code_depnum_ccdc_archive 'CCDC 1531048'
_audit_update_record             
;
2017-02-06 deposited with the CCDC.
2017-04-19 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C50 H38 N2 O'
_chemical_formula_moiety         'C50 H38 N2 O'
_chemical_formula_weight         682.86
_chemical_melting_point          509.25-510.25
_chemical_absolute_configuration 'CHOOSE rm ad rmad syn or unk'

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
_space_group_IT_number           19
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 1/2-X,-Y,1/2+Z
3 1/2+X,1/2-Y,-Z
4 -X,1/2+Y,1/2-Z
#------------------------------------------------------------------------------
_cell_length_a                   10.110(5)
_cell_length_b                   11.948(5)
_cell_length_c                   29.299(14)
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_volume                     3539(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7394
_cell_measurement_theta_min      1.70
_cell_measurement_theta_max      30.17
_cell_measurement_temperature    223
#------------------------------------------------------------------------------
_exptl_crystal_description       prism
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_exptl_crystal_density_diffrn    1.281
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1440.00
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'NUMABS (Rigaku, 1999)'
_exptl_absorpt_correction_T_min  0.968
_exptl_absorpt_correction_T_max  0.992

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      223
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type  'Rigaku Mercury70'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 7.314
_diffrn_reflns_number            28146
_diffrn_reflns_av_R_equivalents  0.0833
_diffrn_reflns_theta_max         27.500
_diffrn_reflns_theta_min         3.262
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_limit_l_max       24
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             8084
_reflns_number_gt                5140
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.784
_reflns_Friedel_fraction_max     0.997
_reflns_Friedel_fraction_full    0.998

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.1303
_refine_ls_R_factor_gt           0.0834
_refine_ls_wR_factor_ref         0.1639
_refine_ls_wR_factor_gt          0.1420
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_reflns         8085
_refine_ls_number_parameters     486
_refine_ls_goodness_of_fit_ref   1.114
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0411P)²+0.3686P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.15
_refine_diff_density_min         -0.17
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;
 Flack x determined using 1283 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.0(10)

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0106 0.0060
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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 0.6722(3) 0.9308(3) 0.04783(9) 0.0476(8) Uani 1 1 d . . . . .
N1 N 0.2750(5) 0.9753(4) 0.10323(15) 0.0592(13) Uani 1 1 d . . . . .
H1 H 0.217(5) 0.948(5) 0.0891(16) 0.065(19) Uiso 1 1 d . . . . .
N2 N 0.7885(5) 1.1218(4) -0.00002(13) 0.0546(11) Uani 1 1 d . . . . .
H2 H 0.701(5) 1.117(4) 0.0007(14) 0.059(16) Uiso 1 1 d . . . . .
C1 C 0.6199(5) 0.8667(4) 0.08294(13) 0.0462(12) Uani 1 1 d . . . . .
C2 C 0.4939(5) 0.8822(4) 0.10049(14) 0.0504(12) Uani 1 1 d . . . . .
C3 C 0.4635(6) 0.8142(5) 0.13738(16) 0.0673(16) Uani 1 1 d . . . . .
H3 H 0.3817 0.8232 0.1522 0.081 Uiso 1 1 calc R U . . .
C4 C 0.5503(6) 0.7339(5) 0.15293(17) 0.0721(17) Uani 1 1 d . . . . .
H4 H 0.5249 0.6894 0.1779 0.086 Uiso 1 1 calc R U . . .
C5 C 0.6721(6) 0.7159(4) 0.13356(15) 0.0611(14) Uani 1 1 d . . . . .
H5 H 0.7284 0.6589 0.1441 0.073 Uiso 1 1 calc R U . . .
C6 C 0.7087(5) 0.7859(4) 0.09770(14) 0.0486(12) Uani 1 1 d . . . . .
C7 C 0.8253(5) 0.7982(4) 0.06947(14) 0.0471(11) Uani 1 1 d . . . . .
C8 C 0.9473(5) 0.7464(5) 0.06604(17) 0.0599(14) Uani 1 1 d . . . . .
H8 H 0.9694 0.6864 0.0853 0.072 Uiso 1 1 calc R U . . .
C9 C 1.0352(5) 0.7844(5) 0.03390(18) 0.0632(15) Uani 1 1 d . . . . .
H9 H 1.1181 0.7495 0.0309 0.076 Uiso 1 1 calc R U . . .
C10 C 1.0030(5) 0.8742(5) 0.00568(17) 0.0588(14) Uani 1 1 d . . . . .
H10 H 1.0659 0.8979 -0.0159 0.071 Uiso 1 1 calc R U . . .
C11 C 0.8840(5) 0.9302(4) 0.00773(15) 0.0496(12) Uani 1 1 d . . . . .
C12 C 0.7981(5) 0.8880(4) 0.04029(15) 0.0473(12) Uani 1 1 d . . . . .
C13 C 0.4012(5) 0.9668(4) 0.07912(14) 0.0506(12) Uani 1 1 d . . . . .
H13 H 0.4447 1.0411 0.0801 0.061 Uiso 1 1 calc R U . . .
C14 C 0.3728(5) 0.9379(4) 0.02903(14) 0.0556(13) Uani 1 1 d . . . . .
H14A H 0.4549 0.9123 0.0146 0.067 Uiso 1 1 calc R U . . .
H14B H 0.3095 0.8757 0.0280 0.067 Uiso 1 1 calc R U . . .
C15 C 0.3175(6) 1.0349(5) 0.00169(18) 0.0754(17) Uani 1 1 d . . . . .
H15A H 0.3018 1.0110 -0.0295 0.090 Uiso 1 1 calc R U . . .
H15B H 0.2349 1.0595 0.0152 0.090 Uiso 1 1 calc R U . . .
H15C H 0.3804 1.0962 0.0018 0.090 Uiso 1 1 calc R U . . .
C16 C 0.2525(5) 1.0413(4) 0.14109(14) 0.0492(12) Uani 1 1 d . . . . .
C17 C 0.3570(5) 1.0965(5) 0.16294(16) 0.0598(14) Uani 1 1 d . . . . .
H17 H 0.4438 1.0864 0.1522 0.072 Uiso 1 1 calc R U . . .
C18 C 0.3350(6) 1.1652(4) 0.19994(16) 0.0618(15) Uani 1 1 d . . . . .
H18 H 0.4068 1.2026 0.2134 0.074 Uiso 1 1 calc R U . . .
C19 C 0.2093(6) 1.1804(5) 0.21766(15) 0.0576(14) Uani 1 1 d . . . . .
C20 C 0.1832(7) 1.2517(5) 0.25652(16) 0.0736(17) Uani 1 1 d . . . . .
H20 H 0.2528 1.2929 0.2696 0.088 Uiso 1 1 calc R U . . .
C21 C 0.0616(7) 1.2600(6) 0.27425(17) 0.081(2) Uani 1 1 d . . . . .
H21 H 0.0487 1.3052 0.3001 0.097 Uiso 1 1 calc R U . . .
C22 C -0.0490(6) 1.2026(5) 0.25523(17) 0.0678(16) Uani 1 1 d . . . . .
C23 C -0.1768(8) 1.2124(6) 0.27269(18) 0.089(2) Uani 1 1 d . . . . .
H23 H -0.1922 1.2568 0.2986 0.107 Uiso 1 1 calc R U . . .
C24 C -0.2802(7) 1.1574(7) 0.2522(2) 0.101(3) Uani 1 1 d . . . . .
H24 H -0.3655 1.1650 0.2645 0.121 Uiso 1 1 calc R U . . .
C25 C -0.2629(6) 1.0918(5) 0.21412(18) 0.0759(18) Uani 1 1 d . . . . .
H25 H -0.3357 1.0553 0.2008 0.091 Uiso 1 1 calc R U . . .
C26 C -0.1377(5) 1.0795(4) 0.19534(15) 0.0547(13) Uani 1 1 d . . . . .
C27 C -0.1127(5) 1.0141(4) 0.15561(15) 0.0534(13) Uani 1 1 d . . . . .
H27 H -0.1841 0.9787 0.1410 0.064 Uiso 1 1 calc R U . . .
C28 C 0.0102(5) 1.0013(4) 0.13826(14) 0.0493(12) Uani 1 1 d . . . . .
H28 H 0.0218 0.9567 0.1122 0.059 Uiso 1 1 calc R U . . .
C29 C 0.1237(5) 1.0539(4) 0.15855(14) 0.0439(11) Uani 1 1 d . . . . .
C30 C 0.1026(5) 1.1225(4) 0.19739(13) 0.0457(11) Uani 1 1 d . . . . .
C31 C -0.0282(5) 1.1347(4) 0.21584(15) 0.0516(13) Uani 1 1 d . . . . .
C32 C 0.8491(5) 1.0267(4) -0.02353(15) 0.0548(13) Uani 1 1 d . . . . .
H32 H 0.9316 1.0532 -0.0382 0.066 Uiso 1 1 calc R U . . .
C33 C 0.7531(7) 0.9908(5) -0.06146(15) 0.0723(17) Uani 1 1 d . . . . .
H33A H 0.6719 0.9626 -0.0473 0.087 Uiso 1 1 calc R U . . .
H33B H 0.7295 1.0570 -0.0795 0.087 Uiso 1 1 calc R U . . .
C34 C 0.8056(8) 0.9036(6) -0.09283(18) 0.096(2) Uani 1 1 d . . . . .
H34A H 0.7393 0.8857 -0.1156 0.116 Uiso 1 1 calc R U . . .
H34B H 0.8847 0.9313 -0.1078 0.116 Uiso 1 1 calc R U . . .
H34C H 0.8270 0.8368 -0.0755 0.116 Uiso 1 1 calc R U . . .
C35 C 0.8466(5) 1.1767(4) 0.03681(14) 0.0460(11) Uani 1 1 d . . . . .
C36 C 0.9829(6) 1.1797(4) 0.04070(16) 0.0561(13) Uani 1 1 d . . . . .
H36 H 1.0354 1.1397 0.0198 0.067 Uiso 1 1 calc R U . . .
C37 C 1.0425(6) 1.2410(5) 0.07503(17) 0.0613(14) Uani 1 1 d . . . . .
H37 H 1.1353 1.2433 0.0765 0.074 Uiso 1 1 calc R U . . .
C38 C 0.9702(6) 1.2990(4) 0.10727(16) 0.0585(14) Uani 1 1 d . . . . .
C39 C 1.0302(7) 1.3619(5) 0.14402(19) 0.0716(17) Uani 1 1 d . . . . .
H39 H 1.1229 1.3664 0.1458 0.086 Uiso 1 1 calc R U . . .
C40 C 0.9573(9) 1.4137(6) 0.1754(2) 0.087(2) Uani 1 1 d . . . . .
H40 H 0.9996 1.4541 0.1987 0.104 Uiso 1 1 calc R U . . .
C41 C 0.8164(8) 1.4094(5) 0.17437(17) 0.0743(19) Uani 1 1 d . . . . .
C42 C 0.7390(10) 1.4581(6) 0.2083(2) 0.097(3) Uani 1 1 d . . . . .
H42 H 0.7799 1.4957 0.2327 0.117 Uiso 1 1 calc R U . . .
C43 C 0.6039(9) 1.4515(5) 0.2065(2) 0.091(2) Uani 1 1 d . . . . .
H43 H 0.5538 1.4837 0.2301 0.109 Uiso 1 1 calc R U . . .
C44 C 0.5394(7) 1.3990(5) 0.1710(2) 0.082(2) Uani 1 1 d . . . . .
H44 H 0.4465 1.3981 0.1699 0.099 Uiso 1 1 calc R U . . .
C45 C 0.6140(7) 1.3468(4) 0.13644(17) 0.0654(16) Uani 1 1 d . . . . .
C46 C 0.5538(6) 1.2877(5) 0.09978(17) 0.0625(15) Uani 1 1 d . . . . .
H46 H 0.4610 1.2859 0.0978 0.075 Uiso 1 1 calc R U . . .
C47 C 0.6267(6) 1.2335(4) 0.06740(15) 0.0554(13) Uani 1 1 d . . . . .
H47 H 0.5834 1.1955 0.0436 0.066 Uiso 1 1 calc R U . . .
C48 C 0.7682(5) 1.2337(4) 0.06909(14) 0.0490(12) Uani 1 1 d . . . . .
C49 C 0.8302(6) 1.2948(4) 0.10461(15) 0.0536(13) Uani 1 1 d . . . . .
C50 C 0.7534(7) 1.3509(4) 0.13833(15) 0.0600(14) Uani 1 1 d . . . . .


#==============================================================================
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_cell_refinement       CrystalClear
_computing_data_reduction        CrystalClear
_computing_structure_solution    'SIR2011 (Burla, et al., 2012)'
_computing_structure_refinement  'SHELXL Version 2014/7 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.2.1 (Rigaku, 2016)'
_computing_molecular_graphics    'CrystalStructure 4.2.1'

#==============================================================================
# MOLECULAR GEOMETRY

_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 C1 1.387(5) . ?
O1 C12 1.390(5) . ?
N1 C16 1.379(6) . ?
N1 C13 1.462(6) . ?
N1 H1 0.79(5) . ?
N2 C35 1.393(6) . ?
N2 C32 1.463(6) . ?
N2 H2 0.88(5) . ?
C1 C2 1.386(7) . ?
C1 C6 1.388(7) . ?
C2 C3 1.387(6) . ?
C2 C13 1.514(7) . ?
C3 C4 1.378(7) . ?
C3 H3 0.9400 . ?
C4 C5 1.373(7) . ?
C4 H4 0.9400 . ?
C5 C6 1.393(6) . ?
C5 H5 0.9400 . ?
C6 C7 1.447(6) . ?
C7 C8 1.383(7) . ?
C7 C12 1.400(6) . ?
C8 C9 1.373(7) . ?
C8 H8 0.9400 . ?
C9 C10 1.393(7) . ?
C9 H9 0.9400 . ?
C10 C11 1.378(7) . ?
C10 H10 0.9400 . ?
C11 C12 1.385(6) . ?
C11 C32 1.514(6) . ?
C13 C14 1.535(6) . ?
C13 H13 0.9900 . ?
C14 C15 1.516(7) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 H15C 0.9700 . ?
C16 C17 1.400(6) . ?
C16 C29 1.408(6) . ?
C17 C18 1.378(7) . ?
C17 H17 0.9400 . ?
C18 C19 1.385(7) . ?
C18 H18 0.9400 . ?
C19 C30 1.412(7) . ?
C19 C20 1.446(7) . ?
C20 C21 1.338(8) . ?
C20 H20 0.9400 . ?
C21 C22 1.425(8) . ?
C21 H21 0.9400 . ?
C22 C23 1.394(8) . ?
C22 C31 1.427(7) . ?
C23 C24 1.373(9) . ?
C23 H23 0.9400 . ?
C24 C25 1.374(8) . ?
C24 H24 0.9400 . ?
C25 C26 1.388(7) . ?
C25 H25 0.9400 . ?
C26 C31 1.421(7) . ?
C26 C27 1.424(6) . ?
C27 C28 1.352(6) . ?
C27 H27 0.9400 . ?
C28 C29 1.436(6) . ?
C28 H28 0.9400 . ?
C29 C30 1.419(6) . ?
C30 C31 1.436(7) . ?
C32 C33 1.536(7) . ?
C32 H32 0.9900 . ?
C33 C34 1.488(7) . ?
C33 H33A 0.9800 . ?
C33 H33B 0.9800 . ?
C34 H34A 0.9700 . ?
C34 H34B 0.9700 . ?
C34 H34C 0.9700 . ?
C35 C36 1.384(7) . ?
C35 C48 1.409(6) . ?
C36 C37 1.382(7) . ?
C36 H36 0.9400 . ?
C37 C38 1.381(7) . ?
C37 H37 0.9400 . ?
C38 C49 1.418(7) . ?
C38 C39 1.447(7) . ?
C39 C40 1.330(8) . ?
C39 H39 0.9400 . ?
C40 C41 1.426(9) . ?
C40 H40 0.9400 . ?
C41 C42 1.393(9) . ?
C41 C50 1.417(7) . ?
C42 C43 1.369(9) . ?
C42 H42 0.9400 . ?
C43 C44 1.377(9) . ?
C43 H43 0.9400 . ?
C44 C45 1.409(7) . ?
C44 H44 0.9400 . ?
C45 C50 1.412(8) . ?
C45 C46 1.422(7) . ?
C46 C47 1.365(7) . ?
C46 H46 0.9400 . ?
C47 C48 1.432(7) . ?
C47 H47 0.9400 . ?
C48 C49 1.417(6) . ?
C49 C50 1.425(7) . ?

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
C1 O1 C12 105.3(4) . . ?
C16 N1 C13 124.9(5) . . ?
C16 N1 H1 122(4) . . ?
C13 N1 H1 112(4) . . ?
C35 N2 C32 123.7(4) . . ?
C35 N2 H2 116(3) . . ?
C32 N2 H2 112(3) . . ?
C2 C1 O1 123.5(4) . . ?
C2 C1 C6 124.9(4) . . ?
O1 C1 C6 111.6(4) . . ?
C1 C2 C3 114.5(5) . . ?
C1 C2 C13 120.3(4) . . ?
C3 C2 C13 125.2(5) . . ?
C4 C3 C2 121.7(5) . . ?
C4 C3 H3 119.2 . . ?
C2 C3 H3 119.2 . . ?
C5 C4 C3 122.9(5) . . ?
C5 C4 H4 118.5 . . ?
C3 C4 H4 118.5 . . ?
C4 C5 C6 117.2(5) . . ?
C4 C5 H5 121.4 . . ?
C6 C5 H5 121.4 . . ?
C1 C6 C5 118.7(5) . . ?
C1 C6 C7 106.2(4) . . ?
C5 C6 C7 135.1(5) . . ?
C8 C7 C12 118.2(5) . . ?
C8 C7 C6 136.2(5) . . ?
C12 C7 C6 105.5(4) . . ?
C9 C8 C7 118.7(5) . . ?
C9 C8 H8 120.7 . . ?
C7 C8 H8 120.7 . . ?
C8 C9 C10 120.7(5) . . ?
C8 C9 H9 119.7 . . ?
C10 C9 H9 119.7 . . ?
C11 C10 C9 123.5(5) . . ?
C11 C10 H10 118.2 . . ?
C9 C10 H10 118.2 . . ?
C10 C11 C12 113.6(5) . . ?
C10 C11 C32 123.2(4) . . ?
C12 C11 C32 123.2(4) . . ?
C11 C12 O1 123.4(4) . . ?
C11 C12 C7 125.2(5) . . ?
O1 C12 C7 111.4(4) . . ?
N1 C13 C2 112.7(4) . . ?
N1 C13 C14 108.3(4) . . ?
C2 C13 C14 111.1(4) . . ?
N1 C13 H13 108.2 . . ?
C2 C13 H13 108.2 . . ?
C14 C13 H13 108.2 . . ?
C15 C14 C13 113.7(4) . . ?
C15 C14 H14A 108.8 . . ?
C13 C14 H14A 108.8 . . ?
C15 C14 H14B 108.8 . . ?
C13 C14 H14B 108.8 . . ?
H14A C14 H14B 107.7 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N1 C16 C17 120.8(5) . . ?
N1 C16 C29 120.4(4) . . ?
C17 C16 C29 118.8(4) . . ?
C18 C17 C16 121.2(5) . . ?
C18 C17 H17 119.4 . . ?
C16 C17 H17 119.4 . . ?
C17 C18 C19 121.4(5) . . ?
C17 C18 H18 119.3 . . ?
C19 C18 H18 119.3 . . ?
C18 C19 C30 118.6(5) . . ?
C18 C19 C20 122.7(5) . . ?
C30 C19 C20 118.7(5) . . ?
C21 C20 C19 121.1(6) . . ?
C21 C20 H20 119.4 . . ?
C19 C20 H20 119.4 . . ?
C20 C21 C22 122.2(5) . . ?
C20 C21 H21 118.9 . . ?
C22 C21 H21 118.9 . . ?
C23 C22 C21 122.9(6) . . ?
C23 C22 C31 118.7(6) . . ?
C21 C22 C31 118.4(5) . . ?
C24 C23 C22 120.3(6) . . ?
C24 C23 H23 119.8 . . ?
C22 C23 H23 119.8 . . ?
C23 C24 C25 122.1(6) . . ?
C23 C24 H24 118.9 . . ?
C25 C24 H24 118.9 . . ?
C24 C25 C26 119.9(6) . . ?
C24 C25 H25 120.1 . . ?
C26 C25 H25 120.1 . . ?
C25 C26 C31 119.6(5) . . ?
C25 C26 C27 122.9(5) . . ?
C31 C26 C27 117.5(5) . . ?
C28 C27 C26 122.2(5) . . ?
C28 C27 H27 118.9 . . ?
C26 C27 H27 118.9 . . ?
C27 C28 C29 122.0(4) . . ?
C27 C28 H28 119.0 . . ?
C29 C28 H28 119.0 . . ?
C16 C29 C30 119.5(4) . . ?
C16 C29 C28 122.8(4) . . ?
C30 C29 C28 117.7(4) . . ?
C19 C30 C29 120.4(5) . . ?
C19 C30 C31 119.7(4) . . ?
C29 C30 C31 119.9(4) . . ?
C26 C31 C22 119.4(5) . . ?
C26 C31 C30 120.8(4) . . ?
C22 C31 C30 119.8(5) . . ?
N2 C32 C11 113.8(4) . . ?
N2 C32 C33 107.0(4) . . ?
C11 C32 C33 111.9(4) . . ?
N2 C32 H32 108.0 . . ?
C11 C32 H32 108.0 . . ?
C33 C32 H32 108.0 . . ?
C34 C33 C32 114.6(5) . . ?
C34 C33 H33A 108.6 . . ?
C32 C33 H33A 108.6 . . ?
C34 C33 H33B 108.6 . . ?
C32 C33 H33B 108.6 . . ?
H33A C33 H33B 107.6 . . ?
C33 C34 H34A 109.5 . . ?
C33 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
C33 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
C36 C35 N2 119.7(5) . . ?
C36 C35 C48 119.5(5) . . ?
N2 C35 C48 120.7(5) . . ?
C37 C36 C35 120.5(5) . . ?
C37 C36 H36 119.7 . . ?
C35 C36 H36 119.7 . . ?
C38 C37 C36 122.2(5) . . ?
C38 C37 H37 118.9 . . ?
C36 C37 H37 118.9 . . ?
C37 C38 C49 118.2(5) . . ?
C37 C38 C39 123.2(6) . . ?
C49 C38 C39 118.6(5) . . ?
C40 C39 C38 121.5(6) . . ?
C40 C39 H39 119.2 . . ?
C38 C39 H39 119.2 . . ?
C39 C40 C41 121.5(6) . . ?
C39 C40 H40 119.2 . . ?
C41 C40 H40 119.2 . . ?
C42 C41 C50 119.1(7) . . ?
C42 C41 C40 122.1(7) . . ?
C50 C41 C40 118.8(6) . . ?
C43 C42 C41 120.5(7) . . ?
C43 C42 H42 119.8 . . ?
C41 C42 H42 119.8 . . ?
C42 C43 C44 121.9(7) . . ?
C42 C43 H43 119.0 . . ?
C44 C43 H43 119.0 . . ?
C43 C44 C45 119.4(7) . . ?
C43 C44 H44 120.3 . . ?
C45 C44 H44 120.3 . . ?
C44 C45 C50 119.4(6) . . ?
C44 C45 C46 122.3(7) . . ?
C50 C45 C46 118.3(5) . . ?
C47 C46 C45 122.0(6) . . ?
C47 C46 H46 119.0 . . ?
C45 C46 H46 119.0 . . ?
C46 C47 C48 121.0(5) . . ?
C46 C47 H47 119.5 . . ?
C48 C47 H47 119.5 . . ?
C35 C48 C49 119.6(5) . . ?
C35 C48 C47 122.5(5) . . ?
C49 C48 C47 117.9(5) . . ?
C48 C49 C38 120.0(5) . . ?
C48 C49 C50 120.7(5) . . ?
C38 C49 C50 119.3(5) . . ?
C45 C50 C41 119.7(6) . . ?
C45 C50 C49 120.1(5) . . ?
C41 C50 C49 120.3(6) . . ?

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
C12 O1 C1 C2 -179.3(4) . . . . ?
C12 O1 C1 C6 0.2(5) . . . . ?
O1 C1 C2 C3 -176.1(4) . . . . ?
C6 C1 C2 C3 4.4(7) . . . . ?
O1 C1 C2 C13 4.6(7) . . . . ?
C6 C1 C2 C13 -174.9(4) . . . . ?
C1 C2 C3 C4 -3.7(8) . . . . ?
C13 C2 C3 C4 175.5(5) . . . . ?
C2 C3 C4 C5 0.5(9) . . . . ?
C3 C4 C5 C6 2.3(9) . . . . ?
C2 C1 C6 C5 -1.8(7) . . . . ?
O1 C1 C6 C5 178.7(4) . . . . ?
C2 C1 C6 C7 178.6(4) . . . . ?
O1 C1 C6 C7 -0.9(5) . . . . ?
C4 C5 C6 C1 -1.7(7) . . . . ?
C4 C5 C6 C7 177.8(5) . . . . ?
C1 C6 C7 C8 179.9(5) . . . . ?
C5 C6 C7 C8 0.3(10) . . . . ?
C1 C6 C7 C12 1.2(5) . . . . ?
C5 C6 C7 C12 -178.3(5) . . . . ?
C12 C7 C8 C9 -0.8(7) . . . . ?
C6 C7 C8 C9 -179.3(5) . . . . ?
C7 C8 C9 C10 0.8(8) . . . . ?
C8 C9 C10 C11 0.0(8) . . . . ?
C9 C10 C11 C12 -0.7(8) . . . . ?
C9 C10 C11 C32 -179.1(4) . . . . ?
C10 C11 C12 O1 -179.2(4) . . . . ?
C32 C11 C12 O1 -0.8(7) . . . . ?
C10 C11 C12 C7 0.7(7) . . . . ?
C32 C11 C12 C7 179.1(4) . . . . ?
C1 O1 C12 C11 -179.5(4) . . . . ?
C1 O1 C12 C7 0.6(5) . . . . ?
C8 C7 C12 C11 0.1(7) . . . . ?
C6 C7 C12 C11 179.0(4) . . . . ?
C8 C7 C12 O1 179.9(4) . . . . ?
C6 C7 C12 O1 -1.2(5) . . . . ?
C16 N1 C13 C2 84.7(6) . . . . ?
C16 N1 C13 C14 -151.9(5) . . . . ?
C1 C2 C13 N1 -177.5(4) . . . . ?
C3 C2 C13 N1 3.3(7) . . . . ?
C1 C2 C13 C14 60.7(6) . . . . ?
C3 C2 C13 C14 -118.5(5) . . . . ?
N1 C13 C14 C15 73.6(6) . . . . ?
C2 C13 C14 C15 -162.0(4) . . . . ?
C13 N1 C16 C17 -7.8(8) . . . . ?
C13 N1 C16 C29 172.4(5) . . . . ?
N1 C16 C17 C18 178.0(5) . . . . ?
C29 C16 C17 C18 -2.2(8) . . . . ?
C16 C17 C18 C19 1.6(8) . . . . ?
C17 C18 C19 C30 0.8(8) . . . . ?
C17 C18 C19 C20 179.8(5) . . . . ?
C18 C19 C20 C21 -176.5(6) . . . . ?
C30 C19 C20 C21 2.4(8) . . . . ?
C19 C20 C21 C22 -2.0(10) . . . . ?
C20 C21 C22 C23 -178.6(6) . . . . ?
C20 C21 C22 C31 -0.3(9) . . . . ?
C21 C22 C23 C24 178.2(7) . . . . ?
C31 C22 C23 C24 -0.1(10) . . . . ?
C22 C23 C24 C25 -0.2(12) . . . . ?
C23 C24 C25 C26 0.0(11) . . . . ?
C24 C25 C26 C31 0.3(9) . . . . ?
C24 C25 C26 C27 -179.1(6) . . . . ?
C25 C26 C27 C28 -178.7(5) . . . . ?
C31 C26 C27 C28 1.9(7) . . . . ?
C26 C27 C28 C29 -0.7(8) . . . . ?
N1 C16 C29 C30 -179.7(4) . . . . ?
C17 C16 C29 C30 0.5(7) . . . . ?
N1 C16 C29 C28 -0.7(7) . . . . ?
C17 C16 C29 C28 179.5(5) . . . . ?
C27 C28 C29 C16 179.8(5) . . . . ?
C27 C28 C29 C30 -1.2(7) . . . . ?
C18 C19 C30 C29 -2.5(7) . . . . ?
C20 C19 C30 C29 178.5(4) . . . . ?
C18 C19 C30 C31 178.4(5) . . . . ?
C20 C19 C30 C31 -0.6(7) . . . . ?
C16 C29 C30 C19 1.8(7) . . . . ?
C28 C29 C30 C19 -177.2(4) . . . . ?
C16 C29 C30 C31 -179.1(4) . . . . ?
C28 C29 C30 C31 1.9(6) . . . . ?
C25 C26 C31 C22 -0.5(8) . . . . ?
C27 C26 C31 C22 178.9(5) . . . . ?
C25 C26 C31 C30 179.4(5) . . . . ?
C27 C26 C31 C30 -1.2(7) . . . . ?
C23 C22 C31 C26 0.4(8) . . . . ?
C21 C22 C31 C26 -178.0(5) . . . . ?
C23 C22 C31 C30 -179.5(5) . . . . ?
C21 C22 C31 C30 2.1(8) . . . . ?
C19 C30 C31 C26 178.4(5) . . . . ?
C29 C30 C31 C26 -0.7(7) . . . . ?
C19 C30 C31 C22 -1.7(7) . . . . ?
C29 C30 C31 C22 179.2(4) . . . . ?
C35 N2 C32 C11 55.4(7) . . . . ?
C35 N2 C32 C33 179.5(4) . . . . ?
C10 C11 C32 N2 -135.1(5) . . . . ?
C12 C11 C32 N2 46.7(7) . . . . ?
C10 C11 C32 C33 103.4(6) . . . . ?
C12 C11 C32 C33 -74.8(6) . . . . ?
N2 C32 C33 C34 172.8(5) . . . . ?
C11 C32 C33 C34 -61.8(6) . . . . ?
C32 N2 C35 C36 28.9(7) . . . . ?
C32 N2 C35 C48 -154.1(5) . . . . ?
N2 C35 C36 C37 175.0(4) . . . . ?
C48 C35 C36 C37 -2.1(7) . . . . ?
C35 C36 C37 C38 1.6(8) . . . . ?
C36 C37 C38 C49 -0.1(8) . . . . ?
C36 C37 C38 C39 178.8(5) . . . . ?
C37 C38 C39 C40 -177.7(5) . . . . ?
C49 C38 C39 C40 1.1(8) . . . . ?
C38 C39 C40 C41 0.2(10) . . . . ?
C39 C40 C41 C42 176.5(6) . . . . ?
C39 C40 C41 C50 -1.8(9) . . . . ?
C50 C41 C42 C43 -1.3(10) . . . . ?
C40 C41 C42 C43 -179.5(6) . . . . ?
C41 C42 C43 C44 -1.2(11) . . . . ?
C42 C43 C44 C45 2.4(10) . . . . ?
C43 C44 C45 C50 -1.1(8) . . . . ?
C43 C44 C45 C46 177.7(5) . . . . ?
C44 C45 C46 C47 -177.3(5) . . . . ?
C50 C45 C46 C47 1.5(8) . . . . ?
C45 C46 C47 C48 0.1(8) . . . . ?
C36 C35 C48 C49 1.0(7) . . . . ?
N2 C35 C48 C49 -176.0(4) . . . . ?
C36 C35 C48 C47 -179.5(4) . . . . ?
N2 C35 C48 C47 3.4(7) . . . . ?
C46 C47 C48 C35 178.6(5) . . . . ?
C46 C47 C48 C49 -1.9(7) . . . . ?
C35 C48 C49 C38 0.5(7) . . . . ?
C47 C48 C49 C38 -179.0(4) . . . . ?
C35 C48 C49 C50 -178.5(4) . . . . ?
C47 C48 C49 C50 2.1(7) . . . . ?
C37 C38 C49 C48 -1.0(7) . . . . ?
C39 C38 C49 C48 -179.9(4) . . . . ?
C37 C38 C49 C50 178.0(4) . . . . ?
C39 C38 C49 C50 -0.9(7) . . . . ?
C44 C45 C50 C41 -1.3(8) . . . . ?
C46 C45 C50 C41 179.9(5) . . . . ?
C44 C45 C50 C49 177.5(5) . . . . ?
C46 C45 C50 C49 -1.3(7) . . . . ?
C42 C41 C50 C45 2.5(8) . . . . ?
C40 C41 C50 C45 -179.2(5) . . . . ?
C42 C41 C50 C49 -176.3(5) . . . . ?
C40 C41 C50 C49 2.0(8) . . . . ?
C48 C49 C50 C45 -0.5(7) . . . . ?
C38 C49 C50 C45 -179.4(4) . . . . ?
C48 C49 C50 C41 178.4(4) . . . . ?
C38 C49 C50 C41 -0.6(7) . . . . ?

#==============================================================================

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.



#==============================================================================
#     End of CIF
#==============================================================================
_chemical_name_systematic        
(R,R)-4,6-Bis(1-(pyren-1-ylamino)propyl)dibenzo[b,d]furan
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: hexane/diethyl ether'
_exptl_crystal_preparation       ', Luminescent'
####################################################################### 
# 
# 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_ike401
_database_code_depnum_ccdc_archive 'CCDC 1531049'
_audit_update_record             
;
2017-02-06 deposited with the CCDC.
2017-04-19 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C50 H38 N2 O'
_chemical_formula_moiety         'C50 H38 N2 O'
_chemical_formula_weight         682.86
_chemical_melting_point          509.45-510.45
_chemical_absolute_configuration 'CHOOSE rm ad rmad syn or unk'

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
_space_group_IT_number           19
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 1/2-X,-Y,1/2+Z
3 1/2+X,1/2-Y,-Z
4 -X,1/2+Y,1/2-Z
#------------------------------------------------------------------------------
_cell_length_a                   10.136(3)
_cell_length_b                   11.918(4)
_cell_length_c                   29.359(8)
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_volume                     3546.4(18)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5317
_cell_measurement_theta_min      1.71
_cell_measurement_theta_max      30.57
_cell_measurement_temperature    223
#------------------------------------------------------------------------------
_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.100
_exptl_crystal_density_diffrn    1.279
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1440.00
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'NUMABS (Rigaku, 1999)'
_exptl_absorpt_correction_T_min  0.976
_exptl_absorpt_correction_T_max  0.992

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      223
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type  'Rigaku Mercury70'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 7.314
_diffrn_reflns_number            28325
_diffrn_reflns_av_R_equivalents  0.1129
_diffrn_reflns_theta_max         27.497
_diffrn_reflns_theta_min         3.260
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_limit_l_max       26
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             8126
_reflns_number_gt                4068
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.785
_reflns_Friedel_fraction_max     0.999
_reflns_Friedel_fraction_full    0.999

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.1874
_refine_ls_R_factor_gt           0.1004
_refine_ls_wR_factor_ref         0.2128
_refine_ls_wR_factor_gt          0.1714
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_reflns         8126
_refine_ls_number_parameters     486
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0521P)²+0.8377P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.18
_refine_diff_density_min         -0.19
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;
 Flack x determined using 910 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -1.0(10)

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0106 0.0060
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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 0.3278(4) 0.0690(4) 0.95211(13) 0.0474(12) Uani 1 1 d . . . . .
N1 N 0.2115(6) -0.1215(5) 0.99990(18) 0.0536(16) Uani 1 1 d . . . . .
H1 H 0.307(7) -0.120(6) 1.001(2) 0.06(2) Uiso 1 1 d . . . . .
N2 N 0.7250(7) 0.0242(6) 0.8968(2) 0.0595(18) Uani 1 1 d . . . . .
H2 H 0.788(7) 0.055(7) 0.909(2) 0.06(3) Uiso 1 1 d . . . . .
C1 C 0.2006(7) 0.1116(6) 0.9599(2) 0.0499(18) Uani 1 1 d . . . . .
C2 C 0.1162(7) 0.0692(6) 0.9923(2) 0.0497(18) Uani 1 1 d . . . . .
C3 C -0.0034(7) 0.1257(7) 0.9944(2) 0.0549(19) Uani 1 1 d . . . . .
H3 H -0.0660 0.1024 1.0160 0.066 Uiso 1 1 calc R U . . .
C4 C -0.0351(7) 0.2149(7) 0.9660(2) 0.062(2) Uani 1 1 d . . . . .
H4 H -0.1179 0.2497 0.9689 0.074 Uiso 1 1 calc R U . . .
C5 C 0.0520(7) 0.2536(7) 0.9335(2) 0.057(2) Uani 1 1 d . . . . .
H5 H 0.0296 0.3130 0.9139 0.069 Uiso 1 1 calc R U . . .
C6 C 0.1750(7) 0.2010(6) 0.9309(2) 0.0479(17) Uani 1 1 d . . . . .
C7 C 0.2906(7) 0.2141(6) 0.9020(2) 0.0480(17) Uani 1 1 d . . . . .
C8 C 0.3273(8) 0.2841(7) 0.8663(2) 0.062(2) Uani 1 1 d . . . . .
H8 H 0.2713 0.3416 0.8560 0.074 Uiso 1 1 calc R U . . .
C9 C 0.4480(8) 0.2660(8) 0.8468(2) 0.071(3) Uani 1 1 d . . . . .
H9 H 0.4725 0.3101 0.8216 0.085 Uiso 1 1 calc R U . . .
C10 C 0.5351(8) 0.1859(7) 0.8623(2) 0.064(2) Uani 1 1 d . . . . .
H10 H 0.6165 0.1773 0.8473 0.077 Uiso 1 1 calc R U . . .
C11 C 0.5063(7) 0.1173(6) 0.8993(2) 0.0506(18) Uani 1 1 d . . . . .
C12 C 0.3798(7) 0.1337(6) 0.91670(19) 0.0456(17) Uani 1 1 d . . . . .
C13 C 0.1512(8) -0.0264(6) 1.0236(2) 0.0541(19) Uani 1 1 d . . . . .
H13 H 0.0691 -0.0530 1.0383 0.065 Uiso 1 1 calc R U . . .
C14 C 0.2480(9) 0.0089(8) 1.0612(2) 0.073(2) Uani 1 1 d . . . . .
H14A H 0.2723 -0.0575 1.0790 0.087 Uiso 1 1 calc R U . . .
H14B H 0.3286 0.0379 1.0469 0.087 Uiso 1 1 calc R U . . .
C15 C 0.1947(10) 0.0958(8) 1.0926(3) 0.093(3) Uani 1 1 d . . . . .
H15A H 0.2606 0.1142 1.1154 0.111 Uiso 1 1 calc R U . . .
H15B H 0.1725 0.1627 1.0754 0.111 Uiso 1 1 calc R U . . .
H15C H 0.1162 0.0673 1.1075 0.111 Uiso 1 1 calc R U . . .
C16 C 0.1537(7) -0.1770(6) 0.9633(2) 0.0489(17) Uani 1 1 d . . . . .
C17 C 0.2317(7) -0.2334(6) 0.9311(2) 0.0474(17) Uani 1 1 d . . . . .
C18 C 0.3723(8) -0.2342(6) 0.9322(2) 0.0547(19) Uani 1 1 d . . . . .
H18 H 0.4158 -0.1957 0.9557 0.066 Uiso 1 1 calc R U . . .
C19 C 0.4456(8) -0.2885(7) 0.9003(2) 0.064(2) Uani 1 1 d . . . . .
H19 H 0.5380 -0.2878 0.9027 0.076 Uiso 1 1 calc R U . . .
C20 C 0.3853(9) -0.3466(7) 0.8634(2) 0.064(2) Uani 1 1 d . . . . .
C21 C 0.4611(10) -0.3998(7) 0.8289(3) 0.079(3) Uani 1 1 d . . . . .
H21 H 0.5538 -0.3995 0.8301 0.094 Uiso 1 1 calc R U . . .
C22 C 0.3952(13) -0.4519(8) 0.7934(3) 0.088(3) Uani 1 1 d . . . . .
H22 H 0.4447 -0.4835 0.7696 0.106 Uiso 1 1 calc R U . . .
C23 C 0.2611(14) -0.4589(8) 0.7919(3) 0.094(3) Uani 1 1 d . . . . .
H23 H 0.2200 -0.4972 0.7677 0.113 Uiso 1 1 calc R U . . .
C24 C 0.1841(11) -0.4092(7) 0.8261(3) 0.072(3) Uani 1 1 d . . . . .
C25 C 0.0444(12) -0.4147(8) 0.8247(3) 0.084(3) Uani 1 1 d . . . . .
H25 H 0.0036 -0.4555 0.8012 0.101 Uiso 1 1 calc R U . . .
C26 C -0.0312(9) -0.3631(7) 0.8559(3) 0.072(3) Uani 1 1 d . . . . .
H26 H -0.1235 -0.3684 0.8540 0.086 Uiso 1 1 calc R U . . .
C27 C 0.0288(8) -0.2991(7) 0.8928(2) 0.0562(19) Uani 1 1 d . . . . .
C28 C -0.0440(8) -0.2411(7) 0.9249(2) 0.060(2) Uani 1 1 d . . . . .
H28 H -0.1366 -0.2432 0.9237 0.072 Uiso 1 1 calc R U . . .
C29 C 0.0182(8) -0.1795(6) 0.9591(2) 0.058(2) Uani 1 1 d . . . . .
H29 H -0.0336 -0.1388 0.9799 0.070 Uiso 1 1 calc R U . . .
C30 C 0.1678(8) -0.2943(6) 0.8953(2) 0.0538(19) Uani 1 1 d . . . . .
C31 C 0.2472(9) -0.3500(6) 0.8615(2) 0.060(2) Uani 1 1 d . . . . .
C32 C 0.5978(7) 0.0335(6) 0.9208(2) 0.0495(18) Uani 1 1 d . . . . .
H32 H 0.5544 -0.0408 0.9200 0.059 Uiso 1 1 calc R U . . .
C33 C 0.6265(7) 0.0621(7) 0.9703(2) 0.057(2) Uani 1 1 d . . . . .
H33A H 0.5446 0.0877 0.9847 0.069 Uiso 1 1 calc R U . . .
H33B H 0.6893 0.1246 0.9712 0.069 Uiso 1 1 calc R U . . .
C34 C 0.6826(8) -0.0350(7) 0.9982(2) 0.075(2) Uani 1 1 d . . . . .
H34A H 0.6982 -0.0102 1.0292 0.090 Uiso 1 1 calc R U . . .
H34B H 0.6202 -0.0967 0.9984 0.090 Uiso 1 1 calc R U . . .
H34C H 0.7651 -0.0598 0.9848 0.090 Uiso 1 1 calc R U . . .
C35 C 0.7472(7) -0.0424(6) 0.8588(2) 0.0494(18) Uani 1 1 d . . . . .
C36 C 0.8769(6) -0.0533(6) 0.84144(19) 0.0420(16) Uani 1 1 d . . . . .
C37 C 0.9886(7) -0.0019(6) 0.8618(2) 0.0499(18) Uani 1 1 d . . . . .
H37 H 0.9766 0.0420 0.8881 0.060 Uiso 1 1 calc R U . . .
C38 C 1.1129(7) -0.0139(6) 0.8445(2) 0.0551(19) Uani 1 1 d . . . . .
H38 H 1.1838 0.0217 0.8592 0.066 Uiso 1 1 calc R U . . .
C39 C 1.1379(7) -0.0788(6) 0.8047(2) 0.0540(19) Uani 1 1 d . . . . .
C40 C 1.2632(8) -0.0925(8) 0.7859(3) 0.078(3) Uani 1 1 d . . . . .
H40 H 1.3364 -0.0573 0.7994 0.094 Uiso 1 1 calc R U . . .
C41 C 1.2801(11) -0.1581(10) 0.7472(3) 0.101(4) Uani 1 1 d . . . . .
H41 H 1.3646 -0.1655 0.7343 0.121 Uiso 1 1 calc R U . . .
C42 C 1.1760(10) -0.2120(9) 0.7277(3) 0.089(3) Uani 1 1 d . . . . .
H42 H 1.1907 -0.2565 0.7017 0.107 Uiso 1 1 calc R U . . .
C43 C 1.0482(9) -0.2032(7) 0.7449(2) 0.067(2) Uani 1 1 d . . . . .
C44 C 0.9374(10) -0.2604(8) 0.7253(3) 0.080(3) Uani 1 1 d . . . . .
H44 H 0.9497 -0.3042 0.6990 0.096 Uiso 1 1 calc R U . . .
C45 C 0.8176(9) -0.2529(7) 0.7435(2) 0.069(2) Uani 1 1 d . . . . .
H45 H 0.7482 -0.2952 0.7310 0.083 Uiso 1 1 calc R U . . .
C46 C 0.7919(8) -0.1799(7) 0.7826(2) 0.055(2) Uani 1 1 d . . . . .
C47 C 0.6665(8) -0.1657(6) 0.8003(2) 0.061(2) Uani 1 1 d . . . . .
H47 H 0.5953 -0.2037 0.7867 0.073 Uiso 1 1 calc R U . . .
C48 C 0.6431(7) -0.0971(6) 0.8373(2) 0.055(2) Uani 1 1 d . . . . .
H48 H 0.5565 -0.0872 0.8480 0.066 Uiso 1 1 calc R U . . .
C49 C 0.8985(7) -0.1230(6) 0.80317(19) 0.0465(17) Uani 1 1 d . . . . .
C50 C 1.0284(8) -0.1339(6) 0.7841(2) 0.053(2) Uani 1 1 d . . . . .


#==============================================================================
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_cell_refinement       CrystalClear
_computing_data_reduction        CrystalClear
_computing_structure_solution    'SIR2011 (Burla, et al., 2012)'
_computing_structure_refinement  'SHELXL Version 2014/7 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.2.1 (Rigaku, 2016)'
_computing_molecular_graphics    'CrystalStructure 4.2.1'

#==============================================================================
# MOLECULAR GEOMETRY

_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 C12 1.398(7) . ?
O1 C1 1.405(8) . ?
N1 C16 1.392(8) . ?
N1 C13 1.463(9) . ?
N1 H1 0.97(7) . ?
N2 C35 1.387(8) . ?
N2 C32 1.473(8) . ?
N2 H2 0.81(7) . ?
C1 C2 1.376(9) . ?
C1 C6 1.389(9) . ?
C2 C3 1.388(9) . ?
C2 C13 1.505(9) . ?
C3 C4 1.390(10) . ?
C3 H3 0.9400 . ?
C4 C5 1.379(10) . ?
C4 H4 0.9400 . ?
C5 C6 1.397(9) . ?
C5 H5 0.9400 . ?
C6 C7 1.455(9) . ?
C7 C12 1.386(9) . ?
C7 C8 1.390(9) . ?
C8 C9 1.368(10) . ?
C8 H8 0.9400 . ?
C9 C10 1.377(10) . ?
C9 H9 0.9400 . ?
C10 C11 1.391(9) . ?
C10 H10 0.9400 . ?
C11 C12 1.394(9) . ?
C11 C32 1.502(9) . ?
C13 C14 1.536(10) . ?
C13 H13 0.9900 . ?
C14 C15 1.488(10) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 H15C 0.9700 . ?
C16 C29 1.380(9) . ?
C16 C17 1.402(9) . ?
C17 C18 1.425(10) . ?
C17 C30 1.432(9) . ?
C18 C19 1.358(9) . ?
C18 H18 0.9400 . ?
C19 C20 1.424(10) . ?
C19 H19 0.9400 . ?
C20 C31 1.401(11) . ?
C20 C21 1.420(10) . ?
C21 C22 1.384(12) . ?
C21 H21 0.9400 . ?
C22 C23 1.362(13) . ?
C22 H22 0.9400 . ?
C23 C24 1.404(12) . ?
C23 H23 0.9400 . ?
C24 C31 1.409(11) . ?
C24 C25 1.418(12) . ?
C25 C26 1.345(12) . ?
C25 H25 0.9400 . ?
C26 C27 1.456(10) . ?
C26 H26 0.9400 . ?
C27 C28 1.383(10) . ?
C27 C30 1.412(10) . ?
C28 C29 1.395(10) . ?
C28 H28 0.9400 . ?
C29 H29 0.9400 . ?
C30 C31 1.441(10) . ?
C32 C33 1.520(8) . ?
C32 H32 0.9900 . ?
C33 C34 1.529(10) . ?
C33 H33A 0.9800 . ?
C33 H33B 0.9800 . ?
C34 H34A 0.9700 . ?
C34 H34B 0.9700 . ?
C34 H34C 0.9700 . ?
C35 C48 1.391(9) . ?
C35 C36 1.417(8) . ?
C36 C49 1.414(8) . ?
C36 C37 1.419(9) . ?
C37 C38 1.366(9) . ?
C37 H37 0.9400 . ?
C38 C39 1.423(9) . ?
C38 H38 0.9400 . ?
C39 C40 1.395(10) . ?
C39 C50 1.424(10) . ?
C40 C41 1.390(11) . ?
C40 H40 0.9400 . ?
C41 C42 1.361(12) . ?
C41 H41 0.9400 . ?
C42 C43 1.395(11) . ?
C42 H42 0.9400 . ?
C43 C50 1.432(10) . ?
C43 C44 1.434(11) . ?
C44 C45 1.329(11) . ?
C44 H44 0.9400 . ?
C45 C46 1.463(10) . ?
C45 H45 0.9400 . ?
C46 C47 1.383(10) . ?
C46 C49 1.412(9) . ?
C47 C48 1.381(9) . ?
C47 H47 0.9400 . ?
C48 H48 0.9400 . ?
C49 C50 1.435(9) . ?

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
C12 O1 C1 105.5(5) . . ?
C16 N1 C13 124.0(6) . . ?
C16 N1 H1 116(4) . . ?
C13 N1 H1 113(4) . . ?
C35 N2 C32 124.8(7) . . ?
C35 N2 H2 118(5) . . ?
C32 N2 H2 116(5) . . ?
C2 C1 C6 126.2(7) . . ?
C2 C1 O1 123.4(6) . . ?
C6 C1 O1 110.4(6) . . ?
C1 C2 C3 113.3(7) . . ?
C1 C2 C13 123.6(7) . . ?
C3 C2 C13 123.1(6) . . ?
C2 C3 C4 123.2(7) . . ?
C2 C3 H3 118.4 . . ?
C4 C3 H3 118.4 . . ?
C5 C4 C3 121.5(7) . . ?
C5 C4 H4 119.2 . . ?
C3 C4 H4 119.2 . . ?
C4 C5 C6 117.3(7) . . ?
C4 C5 H5 121.3 . . ?
C6 C5 H5 121.3 . . ?
C1 C6 C5 118.5(7) . . ?
C1 C6 C7 106.8(6) . . ?
C5 C6 C7 134.6(7) . . ?
C12 C7 C8 118.3(7) . . ?
C12 C7 C6 105.6(6) . . ?
C8 C7 C6 136.0(7) . . ?
C9 C8 C7 117.4(7) . . ?
C9 C8 H8 121.3 . . ?
C7 C8 H8 121.3 . . ?
C8 C9 C10 123.0(7) . . ?
C8 C9 H9 118.5 . . ?
C10 C9 H9 118.5 . . ?
C9 C10 C11 122.0(7) . . ?
C9 C10 H10 119.0 . . ?
C11 C10 H10 119.0 . . ?
C10 C11 C12 113.4(7) . . ?
C10 C11 C32 126.1(7) . . ?
C12 C11 C32 120.5(6) . . ?
C7 C12 C11 125.7(6) . . ?
C7 C12 O1 111.5(6) . . ?
C11 C12 O1 122.8(6) . . ?
N1 C13 C2 113.2(5) . . ?
N1 C13 C14 106.7(6) . . ?
C2 C13 C14 112.4(6) . . ?
N1 C13 H13 108.1 . . ?
C2 C13 H13 108.1 . . ?
C14 C13 H13 108.1 . . ?
C15 C14 C13 113.8(8) . . ?
C15 C14 H14A 108.8 . . ?
C13 C14 H14A 108.8 . . ?
C15 C14 H14B 108.8 . . ?
C13 C14 H14B 108.8 . . ?
H14A C14 H14B 107.7 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C29 C16 N1 119.8(7) . . ?
C29 C16 C17 119.4(7) . . ?
N1 C16 C17 120.7(7) . . ?
C16 C17 C18 123.5(7) . . ?
C16 C17 C30 118.8(7) . . ?
C18 C17 C30 117.7(6) . . ?
C19 C18 C17 122.4(7) . . ?
C19 C18 H18 118.8 . . ?
C17 C18 H18 118.8 . . ?
C18 C19 C20 121.4(8) . . ?
C18 C19 H19 119.3 . . ?
C20 C19 H19 119.3 . . ?
C31 C20 C21 120.0(8) . . ?
C31 C20 C19 118.2(7) . . ?
C21 C20 C19 121.8(9) . . ?
C22 C21 C20 118.4(9) . . ?
C22 C21 H21 120.8 . . ?
C20 C21 H21 120.8 . . ?
C23 C22 C21 122.3(9) . . ?
C23 C22 H22 118.8 . . ?
C21 C22 H22 118.8 . . ?
C22 C23 C24 120.3(10) . . ?
C22 C23 H23 119.9 . . ?
C24 C23 H23 119.9 . . ?
C23 C24 C31 119.2(10) . . ?
C23 C24 C25 120.9(9) . . ?
C31 C24 C25 119.9(8) . . ?
C26 C25 C24 121.8(9) . . ?
C26 C25 H25 119.1 . . ?
C24 C25 H25 119.1 . . ?
C25 C26 C27 120.6(9) . . ?
C25 C26 H26 119.7 . . ?
C27 C26 H26 119.7 . . ?
C28 C27 C30 118.3(7) . . ?
C28 C27 C26 123.1(8) . . ?
C30 C27 C26 118.5(8) . . ?
C27 C28 C29 121.0(7) . . ?
C27 C28 H28 119.5 . . ?
C29 C28 H28 119.5 . . ?
C16 C29 C28 121.6(7) . . ?
C16 C29 H29 119.2 . . ?
C28 C29 H29 119.2 . . ?
C27 C30 C17 120.7(7) . . ?
C27 C30 C31 120.1(7) . . ?
C17 C30 C31 119.2(7) . . ?
C20 C31 C24 119.8(8) . . ?
C20 C31 C30 121.1(7) . . ?
C24 C31 C30 119.1(8) . . ?
N2 C32 C11 112.9(6) . . ?
N2 C32 C33 107.9(6) . . ?
C11 C32 C33 111.8(6) . . ?
N2 C32 H32 108.0 . . ?
C11 C32 H32 108.0 . . ?
C33 C32 H32 108.0 . . ?
C32 C33 C34 114.5(6) . . ?
C32 C33 H33A 108.6 . . ?
C34 C33 H33A 108.6 . . ?
C32 C33 H33B 108.6 . . ?
C34 C33 H33B 108.6 . . ?
H33A C33 H33B 107.6 . . ?
C33 C34 H34A 109.5 . . ?
C33 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
C33 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
N2 C35 C48 120.6(7) . . ?
N2 C35 C36 119.5(6) . . ?
C48 C35 C36 119.8(6) . . ?
C49 C36 C35 118.9(6) . . ?
C49 C36 C37 117.7(6) . . ?
C35 C36 C37 123.3(6) . . ?
C38 C37 C36 122.2(6) . . ?
C38 C37 H37 118.9 . . ?
C36 C37 H37 118.9 . . ?
C37 C38 C39 121.8(7) . . ?
C37 C38 H38 119.1 . . ?
C39 C38 H38 119.1 . . ?
C40 C39 C38 123.5(8) . . ?
C40 C39 C50 119.2(7) . . ?
C38 C39 C50 117.4(7) . . ?
C41 C40 C39 120.2(9) . . ?
C41 C40 H40 119.9 . . ?
C39 C40 H40 119.9 . . ?
C42 C41 C40 120.9(9) . . ?
C42 C41 H41 119.6 . . ?
C40 C41 H41 119.6 . . ?
C41 C42 C43 122.2(8) . . ?
C41 C42 H42 118.9 . . ?
C43 C42 H42 118.9 . . ?
C42 C43 C50 117.7(8) . . ?
C42 C43 C44 123.1(8) . . ?
C50 C43 C44 119.1(7) . . ?
C45 C44 C43 121.5(8) . . ?
C45 C44 H44 119.3 . . ?
C43 C44 H44 119.3 . . ?
C44 C45 C46 121.2(8) . . ?
C44 C45 H45 119.4 . . ?
C46 C45 H45 119.4 . . ?
C47 C46 C49 118.9(7) . . ?
C47 C46 C45 122.1(7) . . ?
C49 C46 C45 119.0(7) . . ?
C48 C47 C46 121.7(7) . . ?
C48 C47 H47 119.1 . . ?
C46 C47 H47 119.1 . . ?
C47 C48 C35 120.3(7) . . ?
C47 C48 H48 119.9 . . ?
C35 C48 H48 119.9 . . ?
C46 C49 C36 120.2(7) . . ?
C46 C49 C50 119.5(6) . . ?
C36 C49 C50 120.3(6) . . ?
C39 C50 C43 119.9(7) . . ?
C39 C50 C49 120.5(6) . . ?
C43 C50 C49 119.6(7) . . ?

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
C12 O1 C1 C2 179.5(6) . . . . ?
C12 O1 C1 C6 -0.9(7) . . . . ?
C6 C1 C2 C3 -0.5(10) . . . . ?
O1 C1 C2 C3 179.1(6) . . . . ?
C6 C1 C2 C13 -178.5(6) . . . . ?
O1 C1 C2 C13 1.1(11) . . . . ?
C1 C2 C3 C4 1.0(10) . . . . ?
C13 C2 C3 C4 179.1(7) . . . . ?
C2 C3 C4 C5 -0.1(12) . . . . ?
C3 C4 C5 C6 -1.3(11) . . . . ?
C2 C1 C6 C5 -1.0(11) . . . . ?
O1 C1 C6 C5 179.4(6) . . . . ?
C2 C1 C6 C7 -178.7(6) . . . . ?
O1 C1 C6 C7 1.7(7) . . . . ?
C4 C5 C6 C1 1.8(10) . . . . ?
C4 C5 C6 C7 178.8(7) . . . . ?
C1 C6 C7 C12 -1.8(8) . . . . ?
C5 C6 C7 C12 -179.0(8) . . . . ?
C1 C6 C7 C8 178.5(8) . . . . ?
C5 C6 C7 C8 1.3(15) . . . . ?
C12 C7 C8 C9 2.4(11) . . . . ?
C6 C7 C8 C9 -177.9(8) . . . . ?
C7 C8 C9 C10 -3.0(12) . . . . ?
C8 C9 C10 C11 -0.1(13) . . . . ?
C9 C10 C11 C12 3.5(11) . . . . ?
C9 C10 C11 C32 -175.4(7) . . . . ?
C8 C7 C12 C11 1.3(11) . . . . ?
C6 C7 C12 C11 -178.5(6) . . . . ?
C8 C7 C12 O1 -178.9(6) . . . . ?
C6 C7 C12 O1 1.3(8) . . . . ?
C10 C11 C12 C7 -4.2(10) . . . . ?
C32 C11 C12 C7 174.8(6) . . . . ?
C10 C11 C12 O1 176.0(6) . . . . ?
C32 C11 C12 O1 -5.0(10) . . . . ?
C1 O1 C12 C7 -0.3(7) . . . . ?
C1 O1 C12 C11 179.5(6) . . . . ?
C16 N1 C13 C2 -55.5(10) . . . . ?
C16 N1 C13 C14 -179.6(6) . . . . ?
C1 C2 C13 N1 -47.0(10) . . . . ?
C3 C2 C13 N1 135.1(7) . . . . ?
C1 C2 C13 C14 74.0(8) . . . . ?
C3 C2 C13 C14 -103.9(8) . . . . ?
N1 C13 C14 C15 -172.7(7) . . . . ?
C2 C13 C14 C15 62.7(9) . . . . ?
C13 N1 C16 C29 -27.9(10) . . . . ?
C13 N1 C16 C17 154.0(7) . . . . ?
C29 C16 C17 C18 179.1(7) . . . . ?
N1 C16 C17 C18 -2.9(11) . . . . ?
C29 C16 C17 C30 -1.3(10) . . . . ?
N1 C16 C17 C30 176.7(6) . . . . ?
C16 C17 C18 C19 -179.3(7) . . . . ?
C30 C17 C18 C19 1.1(11) . . . . ?
C17 C18 C19 C20 1.1(11) . . . . ?
C18 C19 C20 C31 -2.3(11) . . . . ?
C18 C19 C20 C21 177.3(7) . . . . ?
C31 C20 C21 C22 1.4(12) . . . . ?
C19 C20 C21 C22 -178.2(8) . . . . ?
C20 C21 C22 C23 -3.5(15) . . . . ?
C21 C22 C23 C24 2.2(17) . . . . ?
C22 C23 C24 C31 1.4(15) . . . . ?
C22 C23 C24 C25 179.3(9) . . . . ?
C23 C24 C25 C26 -176.8(8) . . . . ?
C31 C24 C25 C26 1.1(14) . . . . ?
C24 C25 C26 C27 0.0(14) . . . . ?
C25 C26 C27 C28 177.6(8) . . . . ?
C25 C26 C27 C30 -1.2(12) . . . . ?
C30 C27 C28 C29 -0.1(11) . . . . ?
C26 C27 C28 C29 -179.0(7) . . . . ?
N1 C16 C29 C28 -175.1(6) . . . . ?
C17 C16 C29 C28 2.9(11) . . . . ?
C27 C28 C29 C16 -2.2(12) . . . . ?
C28 C27 C30 C17 1.7(11) . . . . ?
C26 C27 C30 C17 -179.4(6) . . . . ?
C28 C27 C30 C31 -177.7(7) . . . . ?
C26 C27 C30 C31 1.2(11) . . . . ?
C16 C17 C30 C27 -1.0(10) . . . . ?
C18 C17 C30 C27 178.7(6) . . . . ?
C16 C17 C30 C31 178.4(6) . . . . ?
C18 C17 C30 C31 -2.0(10) . . . . ?
C21 C20 C31 C24 2.0(12) . . . . ?
C19 C20 C31 C24 -178.4(7) . . . . ?
C21 C20 C31 C30 -178.3(7) . . . . ?
C19 C20 C31 C30 1.4(11) . . . . ?
C23 C24 C31 C20 -3.4(12) . . . . ?
C25 C24 C31 C20 178.7(8) . . . . ?
C23 C24 C31 C30 176.9(7) . . . . ?
C25 C24 C31 C30 -1.0(12) . . . . ?
C27 C30 C31 C20 -179.9(7) . . . . ?
C17 C30 C31 C20 0.8(11) . . . . ?
C27 C30 C31 C24 -0.1(11) . . . . ?
C17 C30 C31 C24 -179.5(6) . . . . ?
C35 N2 C32 C11 -84.0(9) . . . . ?
C35 N2 C32 C33 152.0(7) . . . . ?
C10 C11 C32 N2 -3.5(10) . . . . ?
C12 C11 C32 N2 177.6(6) . . . . ?
C10 C11 C32 C33 118.4(8) . . . . ?
C12 C11 C32 C33 -60.5(9) . . . . ?
N2 C32 C33 C34 -73.0(8) . . . . ?
C11 C32 C33 C34 162.3(6) . . . . ?
C32 N2 C35 C48 7.3(11) . . . . ?
C32 N2 C35 C36 -173.6(7) . . . . ?
N2 C35 C36 C49 178.9(6) . . . . ?
C48 C35 C36 C49 -2.0(10) . . . . ?
N2 C35 C36 C37 2.0(10) . . . . ?
C48 C35 C36 C37 -178.9(7) . . . . ?
C49 C36 C37 C38 2.9(10) . . . . ?
C35 C36 C37 C38 179.8(7) . . . . ?
C36 C37 C38 C39 0.2(11) . . . . ?
C37 C38 C39 C40 179.6(7) . . . . ?
C37 C38 C39 C50 -1.7(11) . . . . ?
C38 C39 C40 C41 179.4(8) . . . . ?
C50 C39 C40 C41 0.7(13) . . . . ?
C39 C40 C41 C42 -1.5(15) . . . . ?
C40 C41 C42 C43 0.8(17) . . . . ?
C41 C42 C43 C50 0.6(14) . . . . ?
C41 C42 C43 C44 -179.1(10) . . . . ?
C42 C43 C44 C45 177.9(9) . . . . ?
C50 C43 C44 C45 -1.8(13) . . . . ?
C43 C44 C45 C46 4.1(14) . . . . ?
C44 C45 C46 C47 176.0(8) . . . . ?
C44 C45 C46 C49 -4.7(12) . . . . ?
C49 C46 C47 C48 0.3(11) . . . . ?
C45 C46 C47 C48 179.6(7) . . . . ?
C46 C47 C48 C35 -1.9(11) . . . . ?
N2 C35 C48 C47 -178.2(7) . . . . ?
C36 C35 C48 C47 2.8(11) . . . . ?
C47 C46 C49 C36 0.4(10) . . . . ?
C45 C46 C49 C36 -179.0(6) . . . . ?
C47 C46 C49 C50 -177.8(7) . . . . ?
C45 C46 C49 C50 2.9(10) . . . . ?
C35 C36 C49 C46 0.5(10) . . . . ?
C37 C36 C49 C46 177.6(6) . . . . ?
C35 C36 C49 C50 178.6(6) . . . . ?
C37 C36 C49 C50 -4.3(9) . . . . ?
C40 C39 C50 C43 0.7(11) . . . . ?
C38 C39 C50 C43 -178.1(7) . . . . ?
C40 C39 C50 C49 178.9(7) . . . . ?
C38 C39 C50 C49 0.2(10) . . . . ?
C42 C43 C50 C39 -1.4(11) . . . . ?
C44 C43 C50 C39 178.4(8) . . . . ?
C42 C43 C50 C49 -179.6(8) . . . . ?
C44 C43 C50 C49 0.1(11) . . . . ?
C46 C49 C50 C39 -179.0(7) . . . . ?
C36 C49 C50 C39 2.8(10) . . . . ?
C46 C49 C50 C43 -0.7(10) . . . . ?
C36 C49 C50 C43 -178.9(6) . . . . ?

#==============================================================================

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.



#==============================================================================
#     End of CIF
#==============================================================================
_chemical_name_systematic        
(S,S)-4,6-Bis(1-(pyren-1-ylamino)propyl)dibenzo[b,d]furan
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: hexane/diethyl ether'
_exptl_crystal_preparation       ', Luminescent'
