# Electronic Supplementary Material (ESI) for Chemical Science.
# 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/. 
# 
# 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_TPP
_database_code_depnum_ccdc_archive 'CCDC 1031716'
_audit_update_record             
;
2014-10-30 deposited with the CCDC.
2014-12-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        TPP
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C28 H20 N2'
_chemical_formula_sum            'C28 H20 N2'
_chemical_formula_weight         384.46

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'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'

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

_cell_length_a                   5.9763(5)
_cell_length_b                   11.5786(8)
_cell_length_c                   29.273(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2025.6(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3616
_cell_measurement_theta_min      3.2865
_cell_measurement_theta_max      29.3115

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.261
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             808
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9711
_exptl_absorpt_correction_T_max  0.9883
_exptl_absorpt_process_details   
;
CrysAlis PRO (Agilent Technologies, 2011) 
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.3592
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            13209
_diffrn_reflns_av_R_equivalents  0.0412
_diffrn_reflns_av_sigmaI/netI    0.0260
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         3.29
_diffrn_reflns_theta_max         25.35
_reflns_number_total             2166
_reflns_number_gt                1790
_reflns_threshold_expression     >2sigma(I)

_computing_cell_refinement       'CrysAlis PRO (Agilent Technologies, 2011)'
_computing_data_collection       'CrysAlis PRO'
_computing_data_reduction        'CrysAlis PRO'
_computing_molecular_graphics    'OLEX2 (Dolomanov et al., 2009)'
_computing_publication_material  OLEX2
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0459P)²+0.2636P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -1(4)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         2166
_refine_ls_number_parameters     271
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0528
_refine_ls_R_factor_gt           0.0392
_refine_ls_wR_factor_ref         0.0976
_refine_ls_wR_factor_gt          0.0894
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_restrained_S_all      1.074
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.8875(3) 0.89046(16) 0.09332(7) 0.0388(5) Uani 1 1 d . . .
N2 N 1.1583(3) 0.80046(16) 0.16110(6) 0.0393(5) Uani 1 1 d . . .
C1 C 0.8693(4) 0.77899(19) 0.10535(8) 0.0366(5) Uani 1 1 d . . .
C2 C 1.0079(4) 0.73393(19) 0.13976(8) 0.0370(5) Uani 1 1 d . . .
C3 C 1.1777(4) 0.9119(2) 0.14879(8) 0.0377(5) Uani 1 1 d . . .
C4 C 1.0416(4) 0.95662(19) 0.11380(8) 0.0374(5) Uani 1 1 d . . .
C5 C 0.7009(4) 0.7119(2) 0.07872(8) 0.0379(5) Uani 1 1 d . . .
C6 C 0.5039(4) 0.7659(2) 0.06502(8) 0.0431(6) Uani 1 1 d . . .
H6 H 0.4760 0.8414 0.0743 0.052 Uiso 1 1 calc R . .
C7 C 0.3489(4) 0.7098(2) 0.03794(9) 0.0501(6) Uani 1 1 d . . .
H7 H 0.2167 0.7468 0.0297 0.060 Uiso 1 1 calc R . .
C8 C 0.3911(5) 0.5986(3) 0.02313(9) 0.0548(7) Uani 1 1 d . . .
H8 H 0.2883 0.5607 0.0045 0.066 Uiso 1 1 calc R . .
C9 C 0.5860(5) 0.5439(2) 0.03601(9) 0.0542(7) Uani 1 1 d . . .
H9 H 0.6148 0.4692 0.0259 0.065 Uiso 1 1 calc R . .
C10 C 0.7395(4) 0.5997(2) 0.06395(9) 0.0469(6) Uani 1 1 d . . .
H10 H 0.8694 0.5615 0.0729 0.056 Uiso 1 1 calc R . .
C11 C 0.9951(4) 0.6121(2) 0.15640(8) 0.0394(6) Uani 1 1 d . . .
C12 C 0.8057(5) 0.5724(2) 0.17866(9) 0.0517(7) Uani 1 1 d . . .
H12 H 0.6839 0.6214 0.1827 0.062 Uiso 1 1 calc R . .
C13 C 0.7967(6) 0.4602(2) 0.19487(10) 0.0613(8) Uani 1 1 d . . .
H13 H 0.6706 0.4345 0.2105 0.074 Uiso 1 1 calc R . .
C14 C 0.9730(6) 0.3871(2) 0.18793(11) 0.0613(8) Uani 1 1 d . . .
H14 H 0.9656 0.3114 0.1985 0.074 Uiso 1 1 calc R . .
C15 C 1.1612(5) 0.4249(2) 0.16547(10) 0.0585(8) Uani 1 1 d . . .
H15 H 1.2800 0.3745 0.1605 0.070 Uiso 1 1 calc R . .
C16 C 1.1741(5) 0.5378(2) 0.15019(9) 0.0482(6) Uani 1 1 d . . .
H16 H 1.3031 0.5638 0.1357 0.058 Uiso 1 1 calc R . .
C17 C 1.3456(4) 0.9799(2) 0.17508(8) 0.0397(6) Uani 1 1 d . . .
C18 C 1.5422(4) 0.9267(2) 0.18928(9) 0.0506(7) Uani 1 1 d . . .
H18 H 1.5697 0.8503 0.1812 0.061 Uiso 1 1 calc R . .
C19 C 1.6971(5) 0.9860(3) 0.21528(10) 0.0624(8) Uani 1 1 d . . .
H19 H 1.8292 0.9499 0.2240 0.075 Uiso 1 1 calc R . .
C20 C 1.6570(5) 1.0984(3) 0.22830(10) 0.0686(9) Uani 1 1 d . . .
H20 H 1.7609 1.1376 0.2462 0.082 Uiso 1 1 calc R . .
C21 C 1.4636(6) 1.1524(3) 0.21485(10) 0.0645(9) Uani 1 1 d . . .
H21 H 1.4365 1.2284 0.2235 0.077 Uiso 1 1 calc R . .
C22 C 1.3082(5) 1.0936(2) 0.18825(9) 0.0513(7) Uani 1 1 d . . .
H22 H 1.1776 1.1307 0.1792 0.062 Uiso 1 1 calc R . .
C23 C 1.0590(4) 1.0765(2) 0.09519(8) 0.0423(6) Uani 1 1 d . . .
C24 C 1.2518(5) 1.1137(2) 0.07379(10) 0.0580(7) Uani 1 1 d . . .
H24 H 1.3760 1.0655 0.0723 0.070 Uiso 1 1 calc R . .
C25 C 1.2603(7) 1.2237(3) 0.05443(10) 0.0697(9) Uani 1 1 d . . .
H25 H 1.3890 1.2483 0.0395 0.084 Uiso 1 1 calc R . .
C26 C 1.0792(7) 1.2953(3) 0.05747(12) 0.0761(10) Uani 1 1 d . . .
H26 H 1.0859 1.3689 0.0449 0.091 Uiso 1 1 calc R . .
C27 C 0.8887(6) 1.2596(3) 0.07888(13) 0.0768(10) Uani 1 1 d . . .
H27 H 0.7667 1.3092 0.0811 0.092 Uiso 1 1 calc R . .
C28 C 0.8767(5) 1.1496(2) 0.09725(11) 0.0600(8) Uani 1 1 d . . .
H28 H 0.7450 1.1249 0.1111 0.072 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C4 1.340(3) . ?
N1 C1 1.342(3) . ?
N2 C2 1.338(3) . ?
N2 C3 1.345(3) . ?
C1 C2 1.404(3) . ?
C1 C5 1.491(3) . ?
C2 C11 1.494(3) . ?
C3 C4 1.407(3) . ?
C3 C17 1.489(3) . ?
C4 C23 1.494(3) . ?
C5 C10 1.389(3) . ?
C5 C6 1.392(3) . ?
C6 C7 1.382(4) . ?
C6 H6 0.9300 . ?
C7 C8 1.382(4) . ?
C7 H7 0.9300 . ?
C8 C9 1.378(4) . ?
C8 H8 0.9300 . ?
C9 C10 1.389(4) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C11 C12 1.384(4) . ?
C11 C16 1.385(4) . ?
C12 C13 1.384(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.367(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.374(4) . ?
C14 H14 0.9300 . ?
C15 C16 1.384(4) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C17 C22 1.389(3) . ?
C17 C18 1.390(3) . ?
C18 C19 1.382(4) . ?
C18 H18 0.9300 . ?
C19 C20 1.377(4) . ?
C19 H19 0.9300 . ?
C20 C21 1.372(4) . ?
C20 H20 0.9300 . ?
C21 C22 1.391(4) . ?
C21 H21 0.9300 . ?
C22 H22 0.9300 . ?
C23 C24 1.381(4) . ?
C23 C28 1.381(4) . ?
C24 C25 1.394(4) . ?
C24 H24 0.9300 . ?
C25 C26 1.366(5) . ?
C25 H25 0.9300 . ?
C26 C27 1.364(5) . ?
C26 H26 0.9300 . ?
C27 C28 1.384(4) . ?
C27 H27 0.9300 . ?
C28 H28 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
C4 N1 C1 119.2(2) . . ?
C2 N2 C3 119.0(2) . . ?
N1 C1 C2 119.8(2) . . ?
N1 C1 C5 114.7(2) . . ?
C2 C1 C5 125.4(2) . . ?
N2 C2 C1 121.1(2) . . ?
N2 C2 C11 115.2(2) . . ?
C1 C2 C11 123.7(2) . . ?
N2 C3 C4 119.9(2) . . ?
N2 C3 C17 115.3(2) . . ?
C4 C3 C17 124.8(2) . . ?
N1 C4 C3 120.9(2) . . ?
N1 C4 C23 114.6(2) . . ?
C3 C4 C23 124.5(2) . . ?
C10 C5 C6 118.1(2) . . ?
C10 C5 C1 122.6(2) . . ?
C6 C5 C1 119.2(2) . . ?
C7 C6 C5 121.4(2) . . ?
C7 C6 H6 119.3 . . ?
C5 C6 H6 119.3 . . ?
C6 C7 C8 119.7(3) . . ?
C6 C7 H7 120.1 . . ?
C8 C7 H7 120.1 . . ?
C9 C8 C7 119.8(3) . . ?
C9 C8 H8 120.1 . . ?
C7 C8 H8 120.1 . . ?
C8 C9 C10 120.4(3) . . ?
C8 C9 H9 119.8 . . ?
C10 C9 H9 119.8 . . ?
C9 C10 C5 120.6(2) . . ?
C9 C10 H10 119.7 . . ?
C5 C10 H10 119.7 . . ?
C12 C11 C16 119.2(2) . . ?
C12 C11 C2 120.6(2) . . ?
C16 C11 C2 120.3(2) . . ?
C13 C12 C11 120.3(3) . . ?
C13 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
C14 C13 C12 120.0(3) . . ?
C14 C13 H13 120.0 . . ?
C12 C13 H13 120.0 . . ?
C13 C14 C15 120.3(2) . . ?
C13 C14 H14 119.8 . . ?
C15 C14 H14 119.8 . . ?
C14 C15 C16 120.0(3) . . ?
C14 C15 H15 120.0 . . ?
C16 C15 H15 120.0 . . ?
C15 C16 C11 120.1(3) . . ?
C15 C16 H16 120.0 . . ?
C11 C16 H16 120.0 . . ?
C22 C17 C18 118.2(2) . . ?
C22 C17 C3 122.4(2) . . ?
C18 C17 C3 119.3(2) . . ?
C19 C18 C17 120.7(3) . . ?
C19 C18 H18 119.6 . . ?
C17 C18 H18 119.6 . . ?
C20 C19 C18 120.4(3) . . ?
C20 C19 H19 119.8 . . ?
C18 C19 H19 119.8 . . ?
C21 C20 C19 119.9(3) . . ?
C21 C20 H20 120.1 . . ?
C19 C20 H20 120.1 . . ?
C20 C21 C22 120.0(3) . . ?
C20 C21 H21 120.0 . . ?
C22 C21 H21 120.0 . . ?
C17 C22 C21 120.8(3) . . ?
C17 C22 H22 119.6 . . ?
C21 C22 H22 119.6 . . ?
C24 C23 C28 119.1(2) . . ?
C24 C23 C4 120.9(2) . . ?
C28 C23 C4 119.9(2) . . ?
C23 C24 C25 120.0(3) . . ?
C23 C24 H24 120.0 . . ?
C25 C24 H24 120.0 . . ?
C26 C25 C24 119.9(3) . . ?
C26 C25 H25 120.0 . . ?
C24 C25 H25 120.0 . . ?
C27 C26 C25 120.5(3) . . ?
C27 C26 H26 119.8 . . ?
C25 C26 H26 119.8 . . ?
C26 C27 C28 120.0(3) . . ?
C26 C27 H27 120.0 . . ?
C28 C27 H27 120.0 . . ?
C23 C28 C27 120.4(3) . . ?
C23 C28 H28 119.8 . . ?
C27 C28 H28 119.8 . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.35
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.105
_refine_diff_density_min         -0.149
_refine_diff_density_rms         0.032
_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/. 
# 
# 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_TPP-2P
_database_code_depnum_ccdc_archive 'CCDC 1031717'
_audit_update_record             
;
2014-10-30 deposited with the CCDC.
2014-12-11 downloaded from the CCDC.
;
_audit_creation_date             2014-06-27
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_chemical_name_common            ?
_chemical_name_systematic        TPP-2P
_chemical_formula_moiety         'C40 H28 N2'
_chemical_formula_sum            'C40 H28 N2'
_chemical_formula_weight         536.64
_chemical_melting_point          ?
_chemical_oxdiff_formula         'c10 h10 n2'
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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, -z'

_cell_length_a                   10.6571(9)
_cell_length_b                   11.1264(9)
_cell_length_c                   13.1685(9)
_cell_angle_alpha                88.000(6)
_cell_angle_beta                 76.566(7)
_cell_angle_gamma                74.575(7)
_cell_volume                     1463.4(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1399
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.5725
_cell_measurement_theta_min      3.0873
_exptl_absorpt_coefficient_mu    0.071
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.97604
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.218
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platelet
_exptl_crystal_F_000             564
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.08
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0596
_diffrn_reflns_av_unetI/netI     0.1199
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            9738
_diffrn_reflns_theta_full        25.35
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_min         3.09
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean 10.3592
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0440132000
_diffrn_orient_matrix_UB_12      0.0606926000
_diffrn_orient_matrix_UB_13      0.0024189000
_diffrn_orient_matrix_UB_21      0.0064768000
_diffrn_orient_matrix_UB_22      -0.0031182000
_diffrn_orient_matrix_UB_23      -0.0547493000
_diffrn_orient_matrix_UB_31      -0.0552983000
_diffrn_orient_matrix_UB_32      -0.0261461000
_diffrn_orient_matrix_UB_33      0.0081238000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2233
_reflns_number_total             5333
_reflns_odcompleteness_completeness 99.60
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.354
_refine_diff_density_min         -0.198
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.977
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     379
_refine_ls_number_reflns         5333
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1821
_refine_ls_R_factor_gt           0.0694
_refine_ls_restrained_S_all      0.977
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0758P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1548
_refine_ls_wR_factor_ref         0.2161
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C8(H8), C9(H9), C10(H10), C12(H12), C13(H13), C15(H15),
 C16(H16), C18(H18), C19(H19), C20(H20), C21(H21), C22(H22), C24(H24), C25(H25),
  C26(H26), C27(H27), C28(H28), C30(H30), C31(H31), C33(H33), C34(H34),
 C36(H36), C37(H37), C38(H38), C39(H39), C40(H40)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
N1 N 1.1557(3) 0.5144(3) 0.1130(2) 0.0521(8) Uani 1 d . . .
N2 N 0.9841(3) 0.4360(3) 0.2743(2) 0.0553(9) Uani 1 d . . .
C1 C 1.0258(4) 0.5765(4) 0.1392(3) 0.0494(10) Uani 1 d . . .
C2 C 0.9365(4) 0.5306(4) 0.2172(3) 0.0498(10) Uani 1 d . . .
C3 C 1.1148(4) 0.3794(4) 0.2522(3) 0.0511(10) Uani 1 d . . .
C4 C 1.2001(4) 0.4138(4) 0.1658(3) 0.0491(10) Uani 1 d . . .
C5 C 0.9883(4) 0.6906(4) 0.0785(3) 0.0515(10) Uani 1 d . . .
C6 C 1.0477(4) 0.6905(4) -0.0265(3) 0.0564(11) Uani 1 d . . .
H6 H 1.1120 0.6198 -0.0580 0.068 Uiso 1 calc . . R
C7 C 1.0130(5) 0.7940(5) -0.0856(3) 0.0709(13) Uani 1 d . . .
H7 H 1.0529 0.7921 -0.1565 0.085 Uiso 1 calc . . R
C8 C 0.9198(5) 0.8994(5) -0.0396(5) 0.0856(16) Uani 1 d . . .
H8 H 0.8953 0.9687 -0.0793 0.103 Uiso 1 calc . . R
C9 C 0.8626(5) 0.9021(4) 0.0659(4) 0.0780(14) Uani 1 d . . .
H9 H 0.8009 0.9743 0.0974 0.094 Uiso 1 calc . . R
C10 C 0.8960(4) 0.7988(4) 0.1252(3) 0.0629(12) Uani 1 d . . .
H10 H 0.8569 0.8016 0.1963 0.075 Uiso 1 calc . . R
C11 C 0.7877(4) 0.5776(4) 0.2404(3) 0.0523(10) Uani 1 d . . .
C12 C 0.7183(4) 0.6129(4) 0.1627(3) 0.0537(10) Uani 1 d . . .
H12 H 0.7654 0.6131 0.0937 0.064 Uiso 1 calc . . R
C13 C 0.5802(4) 0.6478(4) 0.1861(3) 0.0579(11) Uani 1 d . . .
H13 H 0.5361 0.6722 0.1325 0.070 Uiso 1 calc . . R
C14 C 0.5059(4) 0.6475(4) 0.2868(3) 0.0563(11) Uani 1 d . . .
C15 C 0.5753(4) 0.6136(4) 0.3649(3) 0.0659(12) Uani 1 d . . .
H15 H 0.5277 0.6139 0.4337 0.079 Uiso 1 calc . . R
C16 C 0.7139(4) 0.5792(4) 0.3426(3) 0.0623(12) Uani 1 d . . .
H16 H 0.7579 0.5570 0.3964 0.075 Uiso 1 calc . . R
C17 C 0.3579(4) 0.6778(4) 0.3088(3) 0.0696(12) Uani 1 d . . .
C18 C 0.2832(5) 0.7729(5) 0.2572(4) 0.0911(16) Uani 1 d . . .
H18 H 0.3281 0.8184 0.2081 0.109 Uiso 1 calc . . R
C19 C 0.1456(5) 0.8012(6) 0.2766(4) 0.1042(18) Uani 1 d . . .
H19 H 0.0983 0.8658 0.2423 0.125 Uiso 1 calc . . R
C20 C 0.0785(6) 0.7307(7) 0.3491(5) 0.1076(19) Uani 1 d . . .
H20 H -0.0142 0.7479 0.3621 0.129 Uiso 1 calc . . R
C21 C 0.1486(6) 0.6359(6) 0.4014(5) 0.1013(18) Uani 1 d . . .
H21 H 0.1036 0.5894 0.4493 0.122 Uiso 1 calc . . R
C22 C 0.2879(5) 0.6107(5) 0.3814(4) 0.0839(15) Uani 1 d . . .
H22 H 0.3348 0.5479 0.4173 0.101 Uiso 1 calc . . R
C23 C 1.3426(4) 0.3456(4) 0.1260(3) 0.0500(10) Uani 1 d . . .
C24 C 1.3812(4) 0.2179(4) 0.1046(3) 0.0641(12) Uani 1 d . . .
H24 H 1.3174 0.1728 0.1186 0.077 Uiso 1 calc . . R
C25 C 1.5140(5) 0.1575(4) 0.0627(3) 0.0714(12) Uani 1 d . . .
H25 H 1.5391 0.0723 0.0474 0.086 Uiso 1 calc . . R
C26 C 1.6091(4) 0.2240(5) 0.0437(3) 0.0679(12) Uani 1 d . . .
H26 H 1.6986 0.1835 0.0164 0.081 Uiso 1 calc . . R
C27 C 1.5718(4) 0.3484(5) 0.0648(3) 0.0667(12) Uani 1 d . . .
H27 H 1.6360 0.3931 0.0515 0.080 Uiso 1 calc . . R
C28 C 1.4399(4) 0.4093(4) 0.1058(3) 0.0590(11) Uani 1 d . . .
H28 H 1.4161 0.4947 0.1200 0.071 Uiso 1 calc . . R
C29 C 1.1598(4) 0.2803(4) 0.3243(3) 0.0527(10) Uani 1 d . . .
C30 C 1.0900(4) 0.1921(4) 0.3555(3) 0.0648(12) Uani 1 d . . .
H30 H 1.0151 0.1938 0.3302 0.078 Uiso 1 calc . . R
C31 C 1.1303(4) 0.1013(4) 0.4240(3) 0.0663(12) Uani 1 d . . .
H31 H 1.0832 0.0413 0.4416 0.080 Uiso 1 calc . . R
C32 C 1.2382(4) 0.0961(4) 0.4675(3) 0.0549(10) Uani 1 d . . .
C33 C 1.3069(4) 0.1856(4) 0.4363(3) 0.0612(11) Uani 1 d . . .
H33 H 1.3804 0.1850 0.4632 0.073 Uiso 1 calc . . R
C34 C 1.2692(4) 0.2761(4) 0.3661(3) 0.0598(11) Uani 1 d . . .
H34 H 1.3177 0.3348 0.3468 0.072 Uiso 1 calc . . R
C35 C 1.2768(4) 0.0011(4) 0.5438(3) 0.0607(11) Uani 1 d . . .
C36 C 1.2528(5) -0.1154(5) 0.5415(3) 0.0782(14) Uani 1 d . . .
H36 H 1.2129 -0.1342 0.4906 0.094 Uiso 1 calc . . R
C37 C 1.2872(5) -0.2038(5) 0.6138(4) 0.0911(16) Uani 1 d . . .
H37 H 1.2701 -0.2812 0.6113 0.109 Uiso 1 calc . . R
C38 C 1.3457(5) -0.1780(6) 0.6879(4) 0.0990(19) Uani 1 d . . .
H38 H 1.3686 -0.2379 0.7363 0.119 Uiso 1 calc . . R
C39 C 1.3718(5) -0.0630(6) 0.6926(4) 0.0960(17) Uani 1 d . . .
H39 H 1.4122 -0.0458 0.7439 0.115 Uiso 1 calc . . R
C40 C 1.3375(5) 0.0262(5) 0.6205(3) 0.0778(14) Uani 1 d . . .
H40 H 1.3552 0.1033 0.6234 0.093 Uiso 1 calc . . R


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C1 1.341(5) . ?
N1 C4 1.333(4) . ?
N2 C2 1.330(4) . ?
N2 C3 1.335(5) . ?
C1 C2 1.410(5) . ?
C1 C5 1.489(5) . ?
C2 C11 1.492(5) . ?
C3 C4 1.393(5) . ?
C3 C29 1.484(5) . ?
C4 C23 1.484(5) . ?
C5 C6 1.380(5) . ?
C5 C10 1.392(6) . ?
C6 H6 0.9300 . ?
C6 C7 1.382(5) . ?
C7 H7 0.9300 . ?
C7 C8 1.370(7) . ?
C8 H8 0.9300 . ?
C8 C9 1.379(7) . ?
C9 H9 0.9300 . ?
C9 C10 1.381(5) . ?
C10 H10 0.9300 . ?
C11 C12 1.385(5) . ?
C11 C16 1.390(5) . ?
C12 H12 0.9300 . ?
C12 C13 1.381(5) . ?
C13 H13 0.9300 . ?
C13 C14 1.378(5) . ?
C14 C15 1.386(5) . ?
C14 C17 1.482(6) . ?
C15 H15 0.9300 . ?
C15 C16 1.386(5) . ?
C16 H16 0.9300 . ?
C17 C18 1.403(6) . ?
C17 C22 1.395(5) . ?
C18 H18 0.9300 . ?
C18 C19 1.378(6) . ?
C19 H19 0.9300 . ?
C19 C20 1.403(7) . ?
C20 H20 0.9300 . ?
C20 C21 1.384(8) . ?
C21 H21 0.9300 . ?
C21 C22 1.397(6) . ?
C22 H22 0.9300 . ?
C23 C24 1.389(5) . ?
C23 C28 1.377(5) . ?
C24 H24 0.9300 . ?
C24 C25 1.385(6) . ?
C25 H25 0.9300 . ?
C25 C26 1.381(5) . ?
C26 H26 0.9300 . ?
C26 C27 1.354(6) . ?
C27 H27 0.9300 . ?
C27 C28 1.375(5) . ?
C28 H28 0.9300 . ?
C29 C30 1.380(5) . ?
C29 C34 1.389(5) . ?
C30 H30 0.9300 . ?
C30 C31 1.379(5) . ?
C31 H31 0.9300 . ?
C31 C32 1.386(5) . ?
C32 C33 1.385(5) . ?
C32 C35 1.478(5) . ?
C33 H33 0.9300 . ?
C33 C34 1.386(5) . ?
C34 H34 0.9300 . ?
C35 C36 1.388(6) . ?
C35 C40 1.391(6) . ?
C36 H36 0.9300 . ?
C36 C37 1.383(6) . ?
C37 H37 0.9300 . ?
C37 C38 1.349(7) . ?
C38 H38 0.9300 . ?
C38 C39 1.386(7) . ?
C39 H39 0.9300 . ?
C39 C40 1.387(6) . ?
C40 H40 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
C4 N1 C1 119.2(3) . . ?
C2 N2 C3 119.7(3) . . ?
N1 C1 C2 119.9(3) . . ?
N1 C1 C5 114.7(3) . . ?
C2 C1 C5 125.3(3) . . ?
N2 C2 C1 119.7(3) . . ?
N2 C2 C11 115.3(3) . . ?
C1 C2 C11 125.0(3) . . ?
N2 C3 C4 120.3(3) . . ?
N2 C3 C29 115.8(3) . . ?
C4 C3 C29 123.9(3) . . ?
N1 C4 C3 120.3(3) . . ?
N1 C4 C23 115.3(3) . . ?
C3 C4 C23 124.4(3) . . ?
C6 C5 C1 119.6(4) . . ?
C6 C5 C10 118.7(4) . . ?
C10 C5 C1 121.7(4) . . ?
C5 C6 H6 119.5 . . ?
C5 C6 C7 121.0(4) . . ?
C7 C6 H6 119.5 . . ?
C6 C7 H7 120.0 . . ?
C8 C7 C6 120.0(4) . . ?
C8 C7 H7 120.0 . . ?
C7 C8 H8 120.2 . . ?
C7 C8 C9 119.7(4) . . ?
C9 C8 H8 120.2 . . ?
C8 C9 H9 119.7 . . ?
C8 C9 C10 120.7(5) . . ?
C10 C9 H9 119.7 . . ?
C5 C10 H10 120.1 . . ?
C9 C10 C5 119.9(4) . . ?
C9 C10 H10 120.1 . . ?
C12 C11 C2 122.4(3) . . ?
C12 C11 C16 117.9(3) . . ?
C16 C11 C2 119.6(3) . . ?
C11 C12 H12 119.5 . . ?
C13 C12 C11 120.9(4) . . ?
C13 C12 H12 119.5 . . ?
C12 C13 H13 119.1 . . ?
C14 C13 C12 121.7(4) . . ?
C14 C13 H13 119.1 . . ?
C13 C14 C15 117.4(3) . . ?
C13 C14 C17 120.5(4) . . ?
C15 C14 C17 122.1(4) . . ?
C14 C15 H15 119.3 . . ?
C16 C15 C14 121.5(4) . . ?
C16 C15 H15 119.3 . . ?
C11 C16 H16 119.7 . . ?
C15 C16 C11 120.6(4) . . ?
C15 C16 H16 119.7 . . ?
C18 C17 C14 122.0(4) . . ?
C22 C17 C14 120.6(4) . . ?
C22 C17 C18 117.5(4) . . ?
C17 C18 H18 118.8 . . ?
C19 C18 C17 122.3(5) . . ?
C19 C18 H18 118.8 . . ?
C18 C19 H19 120.7 . . ?
C18 C19 C20 118.7(5) . . ?
C20 C19 H19 120.7 . . ?
C19 C20 H20 119.6 . . ?
C21 C20 C19 120.7(5) . . ?
C21 C20 H20 119.6 . . ?
C20 C21 H21 120.4 . . ?
C20 C21 C22 119.3(5) . . ?
C22 C21 H21 120.4 . . ?
C17 C22 C21 121.4(5) . . ?
C17 C22 H22 119.3 . . ?
C21 C22 H22 119.3 . . ?
C24 C23 C4 121.5(3) . . ?
C28 C23 C4 120.2(4) . . ?
C28 C23 C24 118.3(4) . . ?
C23 C24 H24 119.8 . . ?
C25 C24 C23 120.4(4) . . ?
C25 C24 H24 119.8 . . ?
C24 C25 H25 120.1 . . ?
C26 C25 C24 119.9(4) . . ?
C26 C25 H25 120.1 . . ?
C25 C26 H26 120.1 . . ?
C27 C26 C25 119.8(4) . . ?
C27 C26 H26 120.1 . . ?
C26 C27 H27 119.7 . . ?
C26 C27 C28 120.6(4) . . ?
C28 C27 H27 119.7 . . ?
C23 C28 H28 119.5 . . ?
C27 C28 C23 121.0(4) . . ?
C27 C28 H28 119.5 . . ?
C30 C29 C3 120.6(3) . . ?
C30 C29 C34 117.8(3) . . ?
C34 C29 C3 121.6(3) . . ?
C29 C30 H30 119.7 . . ?
C31 C30 C29 120.7(4) . . ?
C31 C30 H30 119.7 . . ?
C30 C31 H31 118.7 . . ?
C30 C31 C32 122.5(4) . . ?
C32 C31 H31 118.7 . . ?
C31 C32 C35 121.8(4) . . ?
C33 C32 C31 116.3(3) . . ?
C33 C32 C35 121.8(4) . . ?
C32 C33 H33 119.1 . . ?
C32 C33 C34 121.8(4) . . ?
C34 C33 H33 119.1 . . ?
C29 C34 H34 119.6 . . ?
C33 C34 C29 120.9(3) . . ?
C33 C34 H34 119.6 . . ?
C36 C35 C32 121.0(4) . . ?
C36 C35 C40 118.1(4) . . ?
C40 C35 C32 120.8(4) . . ?
C35 C36 H36 119.5 . . ?
C37 C36 C35 121.1(5) . . ?
C37 C36 H36 119.5 . . ?
C36 C37 H37 119.9 . . ?
C38 C37 C36 120.1(5) . . ?
C38 C37 H37 119.9 . . ?
C37 C38 H38 119.7 . . ?
C37 C38 C39 120.6(5) . . ?
C39 C38 H38 119.7 . . ?
C38 C39 H39 120.2 . . ?
C38 C39 C40 119.7(5) . . ?
C40 C39 H39 120.2 . . ?
C35 C40 H40 119.8 . . ?
C39 C40 C35 120.4(5) . . ?
C39 C40 H40 119.8 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 N2 9.1(5) . . . . ?
N1 C1 C2 C11 -168.8(4) . . . . ?
N1 C1 C5 C6 37.7(5) . . . . ?
N1 C1 C5 C10 -141.1(4) . . . . ?
N1 C4 C23 C24 -128.4(4) . . . . ?
N1 C4 C23 C28 49.3(5) . . . . ?
N2 C2 C11 C12 -140.0(4) . . . . ?
N2 C2 C11 C16 35.8(5) . . . . ?
N2 C3 C4 N1 9.4(6) . . . . ?
N2 C3 C4 C23 -171.1(4) . . . . ?
N2 C3 C29 C30 45.5(5) . . . . ?
N2 C3 C29 C34 -131.7(4) . . . . ?
C1 N1 C4 C3 -5.0(5) . . . . ?
C1 N1 C4 C23 175.4(3) . . . . ?
C1 C2 C11 C12 38.0(6) . . . . ?
C1 C2 C11 C16 -146.2(4) . . . . ?
C1 C5 C6 C7 178.6(3) . . . . ?
C1 C5 C10 C9 -179.2(3) . . . . ?
C2 N2 C3 C4 -4.1(6) . . . . ?
C2 N2 C3 C29 176.1(3) . . . . ?
C2 C1 C5 C6 -140.9(4) . . . . ?
C2 C1 C5 C10 40.3(6) . . . . ?
C2 C11 C12 C13 175.5(4) . . . . ?
C2 C11 C16 C15 -175.1(4) . . . . ?
C3 N2 C2 C1 -4.8(5) . . . . ?
C3 N2 C2 C11 173.3(3) . . . . ?
C3 C4 C23 C24 52.0(5) . . . . ?
C3 C4 C23 C28 -130.3(4) . . . . ?
C3 C29 C30 C31 -178.8(4) . . . . ?
C3 C29 C34 C33 177.6(4) . . . . ?
C4 N1 C1 C2 -4.0(5) . . . . ?
C4 N1 C1 C5 177.4(3) . . . . ?
C4 C3 C29 C30 -134.3(4) . . . . ?
C4 C3 C29 C34 48.6(6) . . . . ?
C4 C23 C24 C25 176.8(4) . . . . ?
C4 C23 C28 C27 -177.3(3) . . . . ?
C5 C1 C2 N2 -172.4(4) . . . . ?
C5 C1 C2 C11 9.7(6) . . . . ?
C5 C6 C7 C8 1.0(6) . . . . ?
C6 C5 C10 C9 1.9(6) . . . . ?
C6 C7 C8 C9 1.0(7) . . . . ?
C7 C8 C9 C10 -1.4(7) . . . . ?
C8 C9 C10 C5 0.0(6) . . . . ?
C10 C5 C6 C7 -2.5(5) . . . . ?
C11 C12 C13 C14 -0.9(6) . . . . ?
C12 C11 C16 C15 0.8(6) . . . . ?
C12 C13 C14 C15 1.6(6) . . . . ?
C12 C13 C14 C17 -176.2(4) . . . . ?
C13 C14 C15 C16 -1.1(6) . . . . ?
C13 C14 C17 C18 -39.7(6) . . . . ?
C13 C14 C17 C22 139.5(4) . . . . ?
C14 C15 C16 C11 -0.1(7) . . . . ?
C14 C17 C18 C19 179.6(5) . . . . ?
C14 C17 C22 C21 -178.4(5) . . . . ?
C15 C14 C17 C18 142.6(5) . . . . ?
C15 C14 C17 C22 -38.2(6) . . . . ?
C16 C11 C12 C13 -0.4(6) . . . . ?
C17 C14 C15 C16 176.6(4) . . . . ?
C17 C18 C19 C20 -1.3(8) . . . . ?
C18 C17 C22 C21 0.8(7) . . . . ?
C18 C19 C20 C21 1.0(9) . . . . ?
C19 C20 C21 C22 0.1(9) . . . . ?
C20 C21 C22 C17 -1.0(8) . . . . ?
C22 C17 C18 C19 0.4(8) . . . . ?
C23 C24 C25 C26 1.1(6) . . . . ?
C24 C23 C28 C27 0.4(6) . . . . ?
C24 C25 C26 C27 -0.9(6) . . . . ?
C25 C26 C27 C28 0.4(6) . . . . ?
C26 C27 C28 C23 -0.2(6) . . . . ?
C28 C23 C24 C25 -0.9(6) . . . . ?
C29 C3 C4 N1 -170.9(4) . . . . ?
C29 C3 C4 C23 8.6(6) . . . . ?
C29 C30 C31 C32 2.3(7) . . . . ?
C30 C29 C34 C33 0.4(6) . . . . ?
C30 C31 C32 C33 -1.7(7) . . . . ?
C30 C31 C32 C35 177.6(4) . . . . ?
C31 C32 C33 C34 0.5(6) . . . . ?
C31 C32 C35 C36 29.5(6) . . . . ?
C31 C32 C35 C40 -150.1(4) . . . . ?
C32 C33 C34 C29 0.1(7) . . . . ?
C32 C35 C36 C37 -179.1(4) . . . . ?
C32 C35 C40 C39 179.2(4) . . . . ?
C33 C32 C35 C36 -151.2(4) . . . . ?
C33 C32 C35 C40 29.2(6) . . . . ?
C34 C29 C30 C31 -1.5(6) . . . . ?
C35 C32 C33 C34 -178.8(4) . . . . ?
C35 C36 C37 C38 -0.3(8) . . . . ?
C36 C35 C40 C39 -0.4(7) . . . . ?
C36 C37 C38 C39 0.0(8) . . . . ?
C37 C38 C39 C40 0.0(8) . . . . ?
C38 C39 C40 C35 0.2(8) . . . . ?
C40 C35 C36 C37 0.5(7) . . . . ?

_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/. 
# 
# 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_TPP-2PM
_database_code_depnum_ccdc_archive 'CCDC 1031718'
_audit_update_record             
;
2014-10-30 deposited with the CCDC.
2014-12-11 downloaded from the CCDC.
;
_audit_creation_date             2014-05-15
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_chemical_name_common            ?
_chemical_name_systematic        TPP-2PM
_chemical_formula_moiety         'C42 H32 N2 O2'
_chemical_formula_sum            'C42 H32 N2 O2'
_chemical_formula_weight         596.70
_chemical_melting_point          ?
_chemical_oxdiff_formula         'c10 h10 n2'
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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, -z'

_cell_length_a                   11.1806(8)
_cell_length_b                   11.4458(7)
_cell_length_c                   12.8610(9)
_cell_angle_alpha                101.527(6)
_cell_angle_beta                 91.283(6)
_cell_angle_gamma                99.274(6)
_cell_volume                     1589.02(19)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2210
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.3660
_cell_measurement_theta_min      2.9973
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74873
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.247
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platelet
_exptl_crystal_F_000             628
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.15
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0316
_diffrn_reflns_av_unetI/netI     0.0565
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            10446
_diffrn_reflns_theta_full        25.35
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_min         3.00
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean 10.3592
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0502808000
_diffrn_orient_matrix_UB_12      0.0112263000
_diffrn_orient_matrix_UB_13      0.0308752000
_diffrn_orient_matrix_UB_21      0.0399904000
_diffrn_orient_matrix_UB_22      0.0254874000
_diffrn_orient_matrix_UB_23      0.0453222000
_diffrn_orient_matrix_UB_31      0.0042164000
_diffrn_orient_matrix_UB_32      0.0578109000
_diffrn_orient_matrix_UB_33      -0.0130745000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                3512
_reflns_number_total             5822
_reflns_odcompleteness_completeness 99.60
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.388
_refine_diff_density_min         -0.191
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     417
_refine_ls_number_reflns         5822
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1027
_refine_ls_R_factor_gt           0.0565
_refine_ls_restrained_S_all      1.010
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0799P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1377
_refine_ls_wR_factor_ref         0.1674
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C9(H9), C10(H10), C12(H12), C13(H13), C15(H15), C16(H16),
 C19(H19), C20(H20), C21(H21), C22(H22), C23(H23), C25(H25), C26(H26), C27(H27),
  C28(H28), C29(H29), C31(H31), C32(H32), C34(H34), C35(H35), C37(H37),
 C38(H38), C40(H40), C41(H41)
2.b Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C42(H42A,H42B,H42C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
O1 O 1.78086(17) -0.22146(18) 0.10452(16) 0.0812(6) Uani 1 d . . .
O2 O 0.7072(2) 0.6098(2) -0.26324(18) 0.1017(7) Uani 1 d . . .
N1 N 0.94311(17) 0.06620(15) 0.24320(15) 0.0480(5) Uani 1 d . . .
N2 N 0.79130(17) -0.01183(15) 0.38913(14) 0.0454(5) Uani 1 d . . .
C1 C 0.9655(2) -0.02524(18) 0.28756(18) 0.0452(5) Uani 1 d . . .
C2 C 0.8810(2) -0.07197(18) 0.35399(17) 0.0449(5) Uani 1 d . . .
C3 C 0.7767(2) 0.08721(18) 0.35214(18) 0.0440(5) Uani 1 d . . .
C4 C 0.8465(2) 0.11913(18) 0.26999(18) 0.0450(5) Uani 1 d . . .
C5 C 1.0838(2) -0.06499(18) 0.26118(18) 0.0458(6) Uani 1 d . . .
C6 C 1.1313(2) -0.0524(2) 0.16399(19) 0.0533(6) Uani 1 d . . .
H6 H 1.0861 -0.0245 0.1154 0.064 Uiso 1 calc . . R
C7 C 1.2428(2) -0.0804(2) 0.1385(2) 0.0539(6) Uani 1 d . . .
H7 H 1.2707 -0.0735 0.0721 0.065 Uiso 1 calc . . R
C8 C 1.3157(2) -0.11917(19) 0.20982(18) 0.0470(6) Uani 1 d . . .
C9 C 1.2680(2) -0.13208(19) 0.30687(19) 0.0496(6) Uani 1 d . . .
H9 H 1.3139 -0.1585 0.3560 0.060 Uiso 1 calc . . R
C10 C 1.1540(2) -0.10657(19) 0.33180(19) 0.0498(6) Uani 1 d . . .
H10 H 1.1240 -0.1174 0.3967 0.060 Uiso 1 calc . . R
C11 C 1.4379(2) -0.1444(2) 0.18236(19) 0.0505(6) Uani 1 d . . .
C12 C 1.5068(2) -0.0821(2) 0.1179(2) 0.0636(7) Uani 1 d . . .
H12 H 1.4758 -0.0220 0.0923 0.076 Uiso 1 calc . . R
C13 C 1.6203(2) -0.1050(2) 0.0897(2) 0.0678(7) Uani 1 d . . .
H13 H 1.6641 -0.0615 0.0451 0.081 Uiso 1 calc . . R
C14 C 1.6680(2) -0.1920(2) 0.1276(2) 0.0611(7) Uani 1 d . . .
C15 C 1.6024(2) -0.2560(2) 0.1937(2) 0.0633(7) Uani 1 d . . .
H15 H 1.6352 -0.3145 0.2204 0.076 Uiso 1 calc . . R
C16 C 1.4882(2) -0.2336(2) 0.2203(2) 0.0592(7) Uani 1 d . . .
H16 H 1.4440 -0.2781 0.2639 0.071 Uiso 1 calc . . R
C17 C 1.8433(3) -0.1699(3) 0.0263(3) 0.0926(10) Uani 1 d . . .
H17A H 1.7952 -0.1930 -0.0396 0.139 Uiso 1 calc . . GR
H17B H 1.9194 -0.1981 0.0168 0.139 Uiso 1 calc . . GR
H17C H 1.8577 -0.0833 0.0483 0.139 Uiso 1 calc . . GR
C18 C 0.8831(2) -0.18712(19) 0.3911(2) 0.0491(6) Uani 1 d . . .
C19 C 0.8994(2) -0.2922(2) 0.3211(2) 0.0667(7) Uani 1 d . . .
H19 H 0.9095 -0.2916 0.2496 0.080 Uiso 1 calc . . R
C20 C 0.9005(3) -0.3976(2) 0.3580(3) 0.0873(10) Uani 1 d . . .
H20 H 0.9091 -0.4685 0.3109 0.105 Uiso 1 calc . . R
C21 C 0.8890(3) -0.3979(3) 0.4648(4) 0.0954(11) Uani 1 d . . .
H21 H 0.8929 -0.4681 0.4897 0.115 Uiso 1 calc . . R
C22 C 0.8718(3) -0.2949(3) 0.5340(3) 0.0838(9) Uani 1 d . . .
H22 H 0.8635 -0.2950 0.6057 0.101 Uiso 1 calc . . R
C23 C 0.8669(2) -0.1912(2) 0.4960(2) 0.0623(7) Uani 1 d . . .
H23 H 0.8522 -0.1223 0.5426 0.075 Uiso 1 calc . . R
C24 C 0.6856(2) 0.15708(19) 0.40444(18) 0.0466(6) Uani 1 d . . .
C25 C 0.5698(2) 0.1009(2) 0.4180(2) 0.0542(6) Uani 1 d . . .
H25 H 0.5476 0.0180 0.3924 0.065 Uiso 1 calc . . R
C26 C 0.4869(2) 0.1653(3) 0.4689(2) 0.0667(7) Uani 1 d . . .
H26 H 0.4090 0.1262 0.4767 0.080 Uiso 1 calc . . R
C27 C 0.5186(3) 0.2869(3) 0.5080(2) 0.0774(9) Uani 1 d . . .
H27 H 0.4623 0.3304 0.5422 0.093 Uiso 1 calc . . R
C28 C 0.6332(3) 0.3445(3) 0.4966(2) 0.0793(9) Uani 1 d . . .
H28 H 0.6553 0.4270 0.5241 0.095 Uiso 1 calc . . R
C29 C 0.7166(3) 0.2795(2) 0.4441(2) 0.0673(7) Uani 1 d . . .
H29 H 0.7940 0.3190 0.4356 0.081 Uiso 1 calc . . R
C30 C 0.8229(2) 0.20703(19) 0.20415(18) 0.0473(6) Uani 1 d . . .
C31 C 0.7058(2) 0.22121(19) 0.17606(19) 0.0530(6) Uani 1 d . . .
H31 H 0.6398 0.1830 0.2065 0.064 Uiso 1 calc . . R
C32 C 0.6867(2) 0.2915(2) 0.10345(19) 0.0524(6) Uani 1 d . . .
H32 H 0.6076 0.2992 0.0858 0.063 Uiso 1 calc . . R
C33 C 0.7817(2) 0.35077(18) 0.05624(19) 0.0484(6) Uani 1 d . . .
C34 C 0.8986(2) 0.3396(2) 0.08705(19) 0.0546(6) Uani 1 d . . .
H34 H 0.9646 0.3807 0.0590 0.066 Uiso 1 calc . . R
C35 C 0.9184(2) 0.2683(2) 0.15868(19) 0.0527(6) Uani 1 d . . .
H35 H 0.9975 0.2614 0.1768 0.063 Uiso 1 calc . . R
C36 C 0.7600(2) 0.42032(19) -0.02607(19) 0.0512(6) Uani 1 d . . .
C37 C 0.6719(3) 0.4926(2) -0.0177(2) 0.0653(7) Uani 1 d . . .
H37 H 0.6254 0.4985 0.0416 0.078 Uiso 1 calc . . R
C38 C 0.6504(3) 0.5568(2) -0.0948(2) 0.0726(8) Uani 1 d . . .
H38 H 0.5903 0.6049 -0.0873 0.087 Uiso 1 calc . . R
C39 C 0.7198(3) 0.5485(2) -0.1840(2) 0.0679(8) Uani 1 d . . .
C40 C 0.8062(3) 0.4757(2) -0.1948(2) 0.0674(7) Uani 1 d . . .
H40 H 0.8516 0.4685 -0.2548 0.081 Uiso 1 calc . . R
C41 C 0.8262(2) 0.4124(2) -0.1166(2) 0.0594(7) Uani 1 d . . .
H41 H 0.8854 0.3634 -0.1249 0.071 Uiso 1 calc . . R
C42 C 0.6185(4) 0.6869(5) -0.2552(3) 0.155(2) Uani 1 d . . .
H42A H 0.6236 0.7280 -0.3135 0.232 Uiso 1 calc . . GR
H42B H 0.6329 0.7452 -0.1894 0.232 Uiso 1 calc . . GR
H42C H 0.5391 0.6394 -0.2574 0.232 Uiso 1 calc . . GR


_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 C14 1.381(3) . ?
O1 C17 1.409(3) . ?
O2 C39 1.365(3) . ?
O2 C42 1.422(4) . ?
N1 C1 1.342(3) . ?
N1 C4 1.340(3) . ?
N2 C2 1.343(3) . ?
N2 C3 1.345(3) . ?
C1 C2 1.402(3) . ?
C1 C5 1.491(3) . ?
C2 C18 1.492(3) . ?
C3 C4 1.399(3) . ?
C3 C24 1.486(3) . ?
C4 C30 1.488(3) . ?
C5 C6 1.393(3) . ?
C5 C10 1.389(3) . ?
C6 H6 0.9300 . ?
C6 C7 1.368(3) . ?
C7 H7 0.9300 . ?
C7 C8 1.396(3) . ?
C8 C9 1.394(3) . ?
C8 C11 1.478(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.383(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.370(3) . ?
C11 C16 1.403(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.379(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.367(4) . ?
C14 C15 1.379(4) . ?
C15 H15 0.9300 . ?
C15 C16 1.379(3) . ?
C16 H16 0.9300 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 C19 1.392(3) . ?
C18 C23 1.374(3) . ?
C19 H19 0.9300 . ?
C19 C20 1.384(4) . ?
C20 H20 0.9300 . ?
C20 C21 1.382(5) . ?
C21 H21 0.9300 . ?
C21 C22 1.371(5) . ?
C22 H22 0.9300 . ?
C22 C23 1.379(3) . ?
C23 H23 0.9300 . ?
C24 C25 1.381(3) . ?
C24 C29 1.376(3) . ?
C25 H25 0.9300 . ?
C25 C26 1.373(3) . ?
C26 H26 0.9300 . ?
C26 C27 1.367(4) . ?
C27 H27 0.9300 . ?
C27 C28 1.369(4) . ?
C28 H28 0.9300 . ?
C28 C29 1.389(4) . ?
C29 H29 0.9300 . ?
C30 C31 1.393(3) . ?
C30 C35 1.387(3) . ?
C31 H31 0.9300 . ?
C31 C32 1.383(3) . ?
C32 H32 0.9300 . ?
C32 C33 1.385(3) . ?
C33 C34 1.390(3) . ?
C33 C36 1.483(3) . ?
C34 H34 0.9300 . ?
C34 C35 1.383(3) . ?
C35 H35 0.9300 . ?
C36 C37 1.378(3) . ?
C36 C41 1.389(3) . ?
C37 H37 0.9300 . ?
C37 C38 1.386(3) . ?
C38 H38 0.9300 . ?
C38 C39 1.395(4) . ?
C39 C40 1.366(4) . ?
C40 H40 0.9300 . ?
C40 C41 1.385(3) . ?
C41 H41 0.9300 . ?
C42 H42A 0.9600 . ?
C42 H42B 0.9600 . ?
C42 H42C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C14 O1 C17 117.5(2) . . ?
C39 O2 C42 118.6(3) . . ?
C4 N1 C1 120.0(2) . . ?
C2 N2 C3 119.30(19) . . ?
N1 C1 C2 119.3(2) . . ?
N1 C1 C5 114.2(2) . . ?
C2 C1 C5 126.48(19) . . ?
N2 C2 C1 120.10(18) . . ?
N2 C2 C18 115.6(2) . . ?
C1 C2 C18 124.3(2) . . ?
N2 C3 C4 119.80(19) . . ?
N2 C3 C24 115.95(19) . . ?
C4 C3 C24 124.25(19) . . ?
N1 C4 C3 119.62(19) . . ?
N1 C4 C30 114.2(2) . . ?
C3 C4 C30 126.1(2) . . ?
C6 C5 C1 118.97(19) . . ?
C10 C5 C1 123.2(2) . . ?
C10 C5 C6 117.6(2) . . ?
C5 C6 H6 119.3 . . ?
C7 C6 C5 121.4(2) . . ?
C7 C6 H6 119.3 . . ?
C6 C7 H7 119.2 . . ?
C6 C7 C8 121.6(2) . . ?
C8 C7 H7 119.2 . . ?
C7 C8 C11 120.7(2) . . ?
C9 C8 C7 117.0(2) . . ?
C9 C8 C11 122.3(2) . . ?
C8 C9 H9 119.2 . . ?
C10 C9 C8 121.5(2) . . ?
C10 C9 H9 119.2 . . ?
C5 C10 H10 119.6 . . ?
C9 C10 C5 120.9(2) . . ?
C9 C10 H10 119.6 . . ?
C12 C11 C8 121.3(2) . . ?
C12 C11 C16 117.1(2) . . ?
C16 C11 C8 121.6(2) . . ?
C11 C12 H12 118.7 . . ?
C11 C12 C13 122.5(2) . . ?
C13 C12 H12 118.7 . . ?
C12 C13 H13 120.2 . . ?
C14 C13 C12 119.6(3) . . ?
C14 C13 H13 120.2 . . ?
C13 C14 O1 124.1(3) . . ?
C13 C14 C15 119.8(2) . . ?
C15 C14 O1 116.1(2) . . ?
C14 C15 H15 119.9 . . ?
C14 C15 C16 120.1(2) . . ?
C16 C15 H15 119.9 . . ?
C11 C16 H16 119.6 . . ?
C15 C16 C11 120.8(2) . . ?
C15 C16 H16 119.6 . . ?
O1 C17 H17A 109.5 . . ?
O1 C17 H17B 109.5 . . ?
O1 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C19 C18 C2 121.3(2) . . ?
C23 C18 C2 120.0(2) . . ?
C23 C18 C19 118.7(2) . . ?
C18 C19 H19 120.1 . . ?
C20 C19 C18 119.9(3) . . ?
C20 C19 H19 120.1 . . ?
C19 C20 H20 119.9 . . ?
C21 C20 C19 120.2(3) . . ?
C21 C20 H20 119.9 . . ?
C20 C21 H21 119.9 . . ?
C22 C21 C20 120.2(3) . . ?
C22 C21 H21 119.9 . . ?
C21 C22 H22 120.3 . . ?
C21 C22 C23 119.3(3) . . ?
C23 C22 H22 120.3 . . ?
C18 C23 C22 121.7(3) . . ?
C18 C23 H23 119.2 . . ?
C22 C23 H23 119.2 . . ?
C25 C24 C3 121.3(2) . . ?
C29 C24 C3 120.3(2) . . ?
C29 C24 C25 118.4(2) . . ?
C24 C25 H25 119.5 . . ?
C26 C25 C24 121.0(2) . . ?
C26 C25 H25 119.5 . . ?
C25 C26 H26 119.9 . . ?
C27 C26 C25 120.1(3) . . ?
C27 C26 H26 119.9 . . ?
C26 C27 H27 120.0 . . ?
C26 C27 C28 120.0(3) . . ?
C28 C27 H27 120.0 . . ?
C27 C28 H28 120.1 . . ?
C27 C28 C29 119.9(3) . . ?
C29 C28 H28 120.1 . . ?
C24 C29 C28 120.6(3) . . ?
C24 C29 H29 119.7 . . ?
C28 C29 H29 119.7 . . ?
C31 C30 C4 122.3(2) . . ?
C35 C30 C4 119.9(2) . . ?
C35 C30 C31 117.5(2) . . ?
C30 C31 H31 119.7 . . ?
C32 C31 C30 120.7(2) . . ?
C32 C31 H31 119.7 . . ?
C31 C32 H32 119.0 . . ?
C31 C32 C33 122.0(2) . . ?
C33 C32 H32 119.0 . . ?
C32 C33 C34 117.2(2) . . ?
C32 C33 C36 121.6(2) . . ?
C34 C33 C36 121.2(2) . . ?
C33 C34 H34 119.4 . . ?
C35 C34 C33 121.2(2) . . ?
C35 C34 H34 119.4 . . ?
C30 C35 H35 119.2 . . ?
C34 C35 C30 121.5(2) . . ?
C34 C35 H35 119.2 . . ?
C37 C36 C33 121.8(2) . . ?
C37 C36 C41 117.2(2) . . ?
C41 C36 C33 121.0(2) . . ?
C36 C37 H37 119.0 . . ?
C36 C37 C38 122.0(3) . . ?
C38 C37 H37 119.0 . . ?
C37 C38 H38 120.3 . . ?
C37 C38 C39 119.3(2) . . ?
C39 C38 H38 120.3 . . ?
O2 C39 C38 123.8(3) . . ?
O2 C39 C40 116.7(3) . . ?
C40 C39 C38 119.6(2) . . ?
C39 C40 H40 120.0 . . ?
C39 C40 C41 120.1(3) . . ?
C41 C40 H40 120.0 . . ?
C36 C41 H41 119.1 . . ?
C40 C41 C36 121.8(2) . . ?
C40 C41 H41 119.1 . . ?
O2 C42 H42A 109.5 . . ?
O2 C42 H42B 109.5 . . ?
O2 C42 H42C 109.5 . . ?
H42A C42 H42B 109.5 . . ?
H42A C42 H42C 109.5 . . ?
H42B C42 H42C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C14 C15 C16 -179.4(2) . . . . ?
O2 C39 C40 C41 178.6(2) . . . . ?
N1 C1 C2 N2 -12.7(3) . . . . ?
N1 C1 C2 C18 167.8(2) . . . . ?
N1 C1 C5 C6 -29.7(3) . . . . ?
N1 C1 C5 C10 145.7(2) . . . . ?
N1 C4 C30 C31 144.2(2) . . . . ?
N1 C4 C30 C35 -28.5(3) . . . . ?
N2 C2 C18 C19 134.1(2) . . . . ?
N2 C2 C18 C23 -44.8(3) . . . . ?
N2 C3 C4 N1 -13.2(3) . . . . ?
N2 C3 C4 C30 165.1(2) . . . . ?
N2 C3 C24 C25 -50.0(3) . . . . ?
N2 C3 C24 C29 127.6(2) . . . . ?
C1 N1 C4 C3 6.6(3) . . . . ?
C1 N1 C4 C30 -171.90(18) . . . . ?
C1 C2 C18 C19 -46.4(3) . . . . ?
C1 C2 C18 C23 134.6(3) . . . . ?
C1 C5 C6 C7 175.9(2) . . . . ?
C1 C5 C10 C9 -174.2(2) . . . . ?
C2 N2 C3 C4 6.6(3) . . . . ?
C2 N2 C3 C24 -172.78(19) . . . . ?
C2 C1 C5 C6 151.8(2) . . . . ?
C2 C1 C5 C10 -32.8(3) . . . . ?
C2 C18 C19 C20 -179.8(3) . . . . ?
C2 C18 C23 C22 -178.1(2) . . . . ?
C3 N2 C2 C1 6.2(3) . . . . ?
C3 N2 C2 C18 -174.35(18) . . . . ?
C3 C4 C30 C31 -34.2(3) . . . . ?
C3 C4 C30 C35 153.1(2) . . . . ?
C3 C24 C25 C26 178.3(2) . . . . ?
C3 C24 C29 C28 -177.5(2) . . . . ?
C4 N1 C1 C2 6.0(3) . . . . ?
C4 N1 C1 C5 -172.61(18) . . . . ?
C4 C3 C24 C25 130.7(2) . . . . ?
C4 C3 C24 C29 -51.7(3) . . . . ?
C4 C30 C31 C32 -171.3(2) . . . . ?
C4 C30 C35 C34 172.2(2) . . . . ?
C5 C1 C2 N2 165.71(19) . . . . ?
C5 C1 C2 C18 -13.7(3) . . . . ?
C5 C6 C7 C8 -2.0(4) . . . . ?
C6 C5 C10 C9 1.3(3) . . . . ?
C6 C7 C8 C9 2.1(3) . . . . ?
C6 C7 C8 C11 -177.6(2) . . . . ?
C7 C8 C9 C10 -0.6(3) . . . . ?
C7 C8 C11 C12 31.3(3) . . . . ?
C7 C8 C11 C16 -148.2(2) . . . . ?
C8 C9 C10 C5 -1.1(3) . . . . ?
C8 C11 C12 C13 -179.0(2) . . . . ?
C8 C11 C16 C15 179.9(2) . . . . ?
C9 C8 C11 C12 -148.4(2) . . . . ?
C9 C8 C11 C16 32.1(3) . . . . ?
C10 C5 C6 C7 0.3(3) . . . . ?
C11 C8 C9 C10 179.16(19) . . . . ?
C11 C12 C13 C14 -0.8(4) . . . . ?
C12 C11 C16 C15 0.4(3) . . . . ?
C12 C13 C14 O1 -179.7(2) . . . . ?
C12 C13 C14 C15 0.0(4) . . . . ?
C13 C14 C15 C16 0.9(4) . . . . ?
C14 C15 C16 C11 -1.1(4) . . . . ?
C16 C11 C12 C13 0.6(4) . . . . ?
C17 O1 C14 C13 -8.7(4) . . . . ?
C17 O1 C14 C15 171.6(2) . . . . ?
C18 C19 C20 C21 -1.8(5) . . . . ?
C19 C18 C23 C22 3.0(4) . . . . ?
C19 C20 C21 C22 2.5(5) . . . . ?
C20 C21 C22 C23 -0.4(5) . . . . ?
C21 C22 C23 C18 -2.4(5) . . . . ?
C23 C18 C19 C20 -0.8(4) . . . . ?
C24 C3 C4 N1 166.0(2) . . . . ?
C24 C3 C4 C30 -15.6(3) . . . . ?
C24 C25 C26 C27 -0.7(4) . . . . ?
C25 C24 C29 C28 0.1(4) . . . . ?
C25 C26 C27 C28 -0.1(4) . . . . ?
C26 C27 C28 C29 0.9(5) . . . . ?
C27 C28 C29 C24 -0.9(4) . . . . ?
C29 C24 C25 C26 0.7(4) . . . . ?
C30 C31 C32 C33 -0.3(4) . . . . ?
C31 C30 C35 C34 -0.9(4) . . . . ?
C31 C32 C33 C34 -1.7(3) . . . . ?
C31 C32 C33 C36 176.5(2) . . . . ?
C32 C33 C34 C35 2.5(3) . . . . ?
C32 C33 C36 C37 41.0(3) . . . . ?
C32 C33 C36 C41 -137.2(2) . . . . ?
C33 C34 C35 C30 -1.2(4) . . . . ?
C33 C36 C37 C38 -179.3(2) . . . . ?
C33 C36 C41 C40 179.2(2) . . . . ?
C34 C33 C36 C37 -140.8(2) . . . . ?
C34 C33 C36 C41 40.9(3) . . . . ?
C35 C30 C31 C32 1.6(3) . . . . ?
C36 C33 C34 C35 -175.8(2) . . . . ?
C36 C37 C38 C39 0.0(4) . . . . ?
C37 C36 C41 C40 0.9(4) . . . . ?
C37 C38 C39 O2 -178.7(3) . . . . ?
C37 C38 C39 C40 1.2(4) . . . . ?
C38 C39 C40 C41 -1.3(4) . . . . ?
C39 C40 C41 C36 0.2(4) . . . . ?
C41 C36 C37 C38 -1.0(4) . . . . ?
C42 O2 C39 C38 0.0(5) . . . . ?
C42 O2 C39 C40 -179.9(3) . . . . ?

_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/. 
# 
# 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_TPP-4M
_database_code_depnum_ccdc_archive 'CCDC 1031719'
_audit_update_record             
;
2014-10-30 deposited with the CCDC.
2014-12-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        TPP-4M
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C32 H28 N2 O4'
_chemical_formula_sum            'C32 H28 N2 O4'
_chemical_formula_weight         504.56

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

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'

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

_cell_length_a                   9.7680(11)
_cell_length_b                   12.3063(14)
_cell_length_c                   12.4687(14)
_cell_angle_alpha                68.542(11)
_cell_angle_beta                 70.492(10)
_cell_angle_gamma                88.089(9)
_cell_volume                     1308.1(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1948
_cell_measurement_theta_min      2.9851
_cell_measurement_theta_max      29.4335

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.281
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             532
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9750
_exptl_absorpt_correction_T_max  0.9866
_exptl_absorpt_process_details   
;
CrysAlis PRO (Agilent Technologies, 2011) 
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.3592
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8065
_diffrn_reflns_av_R_equivalents  0.0340
_diffrn_reflns_av_sigmaI/netI    0.0632
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.99
_diffrn_reflns_theta_max         25.35
_reflns_number_total             4774
_reflns_number_gt                3246
_reflns_threshold_expression     >2sigma(I)

_computing_cell_refinement       'CrysAlis PRO (Agilent Technologies, 2011)'
_computing_data_collection       'CrysAlis PRO'
_computing_data_reduction        'CrysAlis PRO'
_computing_molecular_graphics    'OLEX2 (Dolomanov et al., 2009)'
_computing_publication_material  OLEX2
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0908P)²+3.9827P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.029(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4774
_refine_ls_number_parameters     348
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1215
_refine_ls_R_factor_gt           0.0894
_refine_ls_wR_factor_ref         0.2907
_refine_ls_wR_factor_gt          0.2711
_refine_ls_goodness_of_fit_ref   1.102
_refine_ls_restrained_S_all      1.102
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.5734(5) 0.1380(4) 0.2842(5) 0.0781(15) Uani 1 1 d . . .
O2 O 0.1957(5) -0.0401(3) 0.9655(4) 0.0640(12) Uani 1 1 d . . .
O3 O 0.9573(4) 0.6518(4) 0.9766(3) 0.0530(10) Uani 1 1 d . . .
O4 O 1.1485(5) 0.9832(4) 0.2446(4) 0.0670(13) Uani 1 1 d . . .
N1 N 0.7533(4) 0.5000(3) 0.4856(4) 0.0373(10) Uani 1 1 d . . .
N2 N 0.6414(4) 0.4161(3) 0.7384(4) 0.0365(9) Uani 1 1 d . . .
C1 C 0.6684(5) 0.3983(4) 0.5484(4) 0.0338(10) Uani 1 1 d . . .
C2 C 0.6004(5) 0.3606(4) 0.6778(4) 0.0326(10) Uani 1 1 d . . .
C3 C 0.7389(5) 0.5116(4) 0.6759(4) 0.0331(10) Uani 1 1 d . . .
C4 C 0.7846(5) 0.5604(4) 0.5466(4) 0.0335(10) Uani 1 1 d . . .
C5 C 0.6491(5) 0.3318(4) 0.4759(4) 0.0350(11) Uani 1 1 d . . .
C6 C 0.6131(5) 0.3873(5) 0.3722(4) 0.0405(12) Uani 1 1 d . . .
H6 H 0.6062 0.4678 0.3467 0.049 Uiso 1 1 calc R . .
C7 C 0.5868(6) 0.3274(5) 0.3045(5) 0.0486(13) Uani 1 1 d . . .
H7 H 0.5610 0.3670 0.2357 0.058 Uiso 1 1 calc R . .
C8 C 0.5994(6) 0.2081(5) 0.3407(5) 0.0501(14) Uani 1 1 d . . .
C9 C 0.6396(6) 0.1514(5) 0.4432(6) 0.0520(14) Uani 1 1 d . . .
H9 H 0.6503 0.0715 0.4668 0.062 Uiso 1 1 calc R . .
C10 C 0.6638(6) 0.2110(5) 0.5097(5) 0.0449(12) Uani 1 1 d . . .
H10 H 0.6902 0.1712 0.5780 0.054 Uiso 1 1 calc R . .
C11 C 0.5406(11) 0.1935(9) 0.1754(9) 0.112(3) Uani 1 1 d . . .
H11A H 0.6236 0.2453 0.1126 0.168 Uiso 1 1 calc R . .
H11B H 0.4586 0.2378 0.1915 0.168 Uiso 1 1 calc R . .
H11C H 0.5173 0.1351 0.1483 0.168 Uiso 1 1 calc R . .
C12 C 0.4867(5) 0.2596(4) 0.7531(4) 0.0348(11) Uani 1 1 d . . .
C13 C 0.3827(5) 0.2331(4) 0.7104(4) 0.0386(11) Uani 1 1 d . . .
H13 H 0.3802 0.2824 0.6341 0.046 Uiso 1 1 calc R . .
C14 C 0.2829(5) 0.1348(5) 0.7793(5) 0.0447(13) Uani 1 1 d . . .
H14 H 0.2151 0.1175 0.7488 0.054 Uiso 1 1 calc R . .
C15 C 0.2841(5) 0.0623(4) 0.8935(5) 0.0425(12) Uani 1 1 d . . .
C16 C 0.3805(5) 0.0916(5) 0.9408(5) 0.0459(13) Uani 1 1 d . . .
H16 H 0.3776 0.0453 1.0197 0.055 Uiso 1 1 calc R . .
C17 C 0.4805(5) 0.1887(5) 0.8718(4) 0.0412(12) Uani 1 1 d . . .
H17 H 0.5450 0.2075 0.9044 0.049 Uiso 1 1 calc R . .
C18 C 0.1051(8) -0.0793(6) 0.9146(7) 0.081(2) Uani 1 1 d . . .
H18A H 0.1641 -0.0827 0.8372 0.122 Uiso 1 1 calc R . .
H18B H 0.0331 -0.0256 0.9025 0.122 Uiso 1 1 calc R . .
H18C H 0.0573 -0.1559 0.9700 0.122 Uiso 1 1 calc R . .
C19 C 0.7935(5) 0.5548(4) 0.7522(4) 0.0337(10) Uani 1 1 d . . .
C20 C 0.7025(5) 0.5423(5) 0.8699(5) 0.0433(13) Uani 1 1 d . . .
H20 H 0.6061 0.5109 0.8975 0.052 Uiso 1 1 calc R . .
C21 C 0.7513(6) 0.5752(5) 0.9471(5) 0.0447(13) Uani 1 1 d . . .
H21 H 0.6875 0.5677 1.0244 0.054 Uiso 1 1 calc R . .
C22 C 0.8956(5) 0.6192(4) 0.9083(5) 0.0386(11) Uani 1 1 d . . .
C23 C 0.9879(5) 0.6319(4) 0.7903(5) 0.0404(12) Uani 1 1 d . . .
H23 H 1.0847 0.6620 0.7631 0.049 Uiso 1 1 calc R . .
C24 C 0.9381(5) 0.6009(4) 0.7144(5) 0.0376(11) Uani 1 1 d . . .
H24 H 1.0015 0.6106 0.6362 0.045 Uiso 1 1 calc R . .
C25 C 0.8688(7) 0.6368(6) 1.0975(5) 0.0594(16) Uani 1 1 d . . .
H25A H 0.7948 0.6901 1.0950 0.089 Uiso 1 1 calc R . .
H25B H 0.9279 0.6526 1.1391 0.089 Uiso 1 1 calc R . .
H25C H 0.8235 0.5576 1.1406 0.089 Uiso 1 1 calc R . .
C26 C 0.8725(5) 0.6751(4) 0.4685(4) 0.0346(11) Uani 1 1 d . . .
C27 C 0.8450(6) 0.7748(4) 0.4952(5) 0.0449(13) Uani 1 1 d . . .
H27 H 0.7656 0.7713 0.5636 0.054 Uiso 1 1 calc R . .
C28 C 0.9328(6) 0.8805(5) 0.4227(5) 0.0503(14) Uani 1 1 d . . .
H28 H 0.9116 0.9467 0.4421 0.060 Uiso 1 1 calc R . .
C29 C 1.0522(6) 0.8858(5) 0.3213(5) 0.0443(13) Uani 1 1 d . . .
C30 C 1.0790(5) 0.7882(5) 0.2903(5) 0.0448(13) Uani 1 1 d . . .
H30 H 1.1573 0.7924 0.2208 0.054 Uiso 1 1 calc R . .
C31 C 0.9901(5) 0.6846(4) 0.3620(4) 0.0402(12) Uani 1 1 d . . .
H31 H 1.0082 0.6200 0.3394 0.048 Uiso 1 1 calc R . .
C32 C 1.1211(10) 1.0891(6) 0.2643(8) 0.091(3) Uani 1 1 d . . .
H32A H 1.1876 1.1523 0.1971 0.136 Uiso 1 1 calc R . .
H32B H 1.1344 1.0820 0.3394 0.136 Uiso 1 1 calc R . .
H32C H 1.0226 1.1051 0.2698 0.136 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C8 1.373(6) . ?
O1 C11 1.418(10) . ?
O2 C15 1.367(6) . ?
O2 C18 1.430(8) . ?
O3 C22 1.362(6) . ?
O3 C25 1.412(7) . ?
O4 C29 1.368(6) . ?
O4 C32 1.414(8) . ?
N1 C1 1.336(6) . ?
N1 C4 1.345(6) . ?
N2 C2 1.340(6) . ?
N2 C3 1.343(6) . ?
C1 C2 1.421(6) . ?
C1 C5 1.479(6) . ?
C2 C12 1.483(6) . ?
C3 C4 1.410(6) . ?
C3 C19 1.483(6) . ?
C4 C26 1.482(6) . ?
C5 C6 1.380(7) . ?
C5 C10 1.406(7) . ?
C6 C7 1.392(7) . ?
C6 H6 0.9300 . ?
C7 C8 1.384(8) . ?
C7 H7 0.9300 . ?
C8 C9 1.392(8) . ?
C9 C10 1.367(7) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 C13 1.390(7) . ?
C12 C17 1.398(7) . ?
C13 C14 1.383(7) . ?
C13 H13 0.9300 . ?
C14 C15 1.379(7) . ?
C14 H14 0.9300 . ?
C15 C16 1.384(7) . ?
C16 C17 1.374(7) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 C20 1.393(7) . ?
C19 C24 1.397(6) . ?
C20 C21 1.386(7) . ?
C20 H20 0.9300 . ?
C21 C22 1.385(7) . ?
C21 H21 0.9300 . ?
C22 C23 1.399(7) . ?
C23 C24 1.364(7) . ?
C23 H23 0.9300 . ?
C24 H24 0.9300 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
C26 C27 1.381(7) . ?
C26 C31 1.404(7) . ?
C27 C28 1.393(7) . ?
C27 H27 0.9300 . ?
C28 C29 1.387(8) . ?
C28 H28 0.9300 . ?
C29 C30 1.383(7) . ?
C30 C31 1.378(7) . ?
C30 H30 0.9300 . ?
C31 H31 0.9300 . ?
C32 H32A 0.9600 . ?
C32 H32B 0.9600 . ?
C32 H32C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 O1 C11 117.3(6) . . ?
C15 O2 C18 117.6(5) . . ?
C22 O3 C25 117.7(4) . . ?
C29 O4 C32 118.4(5) . . ?
C1 N1 C4 119.6(4) . . ?
C2 N2 C3 120.0(4) . . ?
N1 C1 C2 119.8(4) . . ?
N1 C1 C5 116.6(4) . . ?
C2 C1 C5 123.6(4) . . ?
N2 C2 C1 119.5(4) . . ?
N2 C2 C12 116.6(4) . . ?
C1 C2 C12 123.9(4) . . ?
N2 C3 C4 119.4(4) . . ?
N2 C3 C19 115.3(4) . . ?
C4 C3 C19 125.3(4) . . ?
N1 C4 C3 120.0(4) . . ?
N1 C4 C26 115.3(4) . . ?
C3 C4 C26 124.6(4) . . ?
C6 C5 C10 117.4(5) . . ?
C6 C5 C1 120.3(4) . . ?
C10 C5 C1 122.3(4) . . ?
C5 C6 C7 122.4(5) . . ?
C5 C6 H6 118.8 . . ?
C7 C6 H6 118.8 . . ?
C8 C7 C6 119.1(5) . . ?
C8 C7 H7 120.5 . . ?
C6 C7 H7 120.5 . . ?
O1 C8 C7 125.2(6) . . ?
O1 C8 C9 115.7(5) . . ?
C7 C8 C9 119.2(5) . . ?
C10 C9 C8 121.2(5) . . ?
C10 C9 H9 119.4 . . ?
C8 C9 H9 119.4 . . ?
C9 C10 C5 120.7(5) . . ?
C9 C10 H10 119.7 . . ?
C5 C10 H10 119.7 . . ?
O1 C11 H11A 109.5 . . ?
O1 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
O1 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C13 C12 C17 117.9(4) . . ?
C13 C12 C2 122.1(4) . . ?
C17 C12 C2 120.0(4) . . ?
C14 C13 C12 121.1(5) . . ?
C14 C13 H13 119.4 . . ?
C12 C13 H13 119.4 . . ?
C15 C14 C13 119.8(5) . . ?
C15 C14 H14 120.1 . . ?
C13 C14 H14 120.1 . . ?
O2 C15 C14 124.2(5) . . ?
O2 C15 C16 116.0(5) . . ?
C14 C15 C16 119.8(4) . . ?
C17 C16 C15 120.2(5) . . ?
C17 C16 H16 119.9 . . ?
C15 C16 H16 119.9 . . ?
C16 C17 C12 120.9(5) . . ?
C16 C17 H17 119.6 . . ?
C12 C17 H17 119.6 . . ?
O2 C18 H18A 109.5 . . ?
O2 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
O2 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C20 C19 C24 117.4(4) . . ?
C20 C19 C3 120.0(4) . . ?
C24 C19 C3 122.5(4) . . ?
C21 C20 C19 122.0(4) . . ?
C21 C20 H20 119.0 . . ?
C19 C20 H20 119.0 . . ?
C22 C21 C20 119.7(5) . . ?
C22 C21 H21 120.2 . . ?
C20 C21 H21 120.2 . . ?
O3 C22 C21 125.2(5) . . ?
O3 C22 C23 116.1(4) . . ?
C21 C22 C23 118.7(4) . . ?
C24 C23 C22 121.1(4) . . ?
C24 C23 H23 119.4 . . ?
C22 C23 H23 119.4 . . ?
C23 C24 C19 121.1(4) . . ?
C23 C24 H24 119.4 . . ?
C19 C24 H24 119.4 . . ?
O3 C25 H25A 109.5 . . ?
O3 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
O3 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C27 C26 C31 117.6(4) . . ?
C27 C26 C4 123.1(4) . . ?
C31 C26 C4 119.4(4) . . ?
C26 C27 C28 121.9(5) . . ?
C26 C27 H27 119.0 . . ?
C28 C27 H27 119.0 . . ?
C29 C28 C27 119.2(5) . . ?
C29 C28 H28 120.4 . . ?
C27 C28 H28 120.4 . . ?
O4 C29 C30 115.2(5) . . ?
O4 C29 C28 124.9(5) . . ?
C30 C29 C28 119.9(5) . . ?
C31 C30 C29 120.2(5) . . ?
C31 C30 H30 119.9 . . ?
C29 C30 H30 119.9 . . ?
C30 C31 C26 121.1(5) . . ?
C30 C31 H31 119.4 . . ?
C26 C31 H31 119.4 . . ?
O4 C32 H32A 109.5 . . ?
O4 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
O4 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.35
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.360
_refine_diff_density_min         -0.280
_refine_diff_density_rms         0.074
_exptl_crystal_preparation       Luminescent
