# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_cd21251
_audit_block_doi                 10.5517/ccyv2b5
_database_code_depnum_ccdc_archive 'CCDC 888997'
_audit_update_record             
;
2015-11-30 deposited with the CCDC.
2016-03-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C34.50 H25 Cl N2 O2'
_chemical_formula_weight         535.02

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   C2/c

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

_cell_length_a                   15.3088(9)
_cell_length_b                   17.9930(11)
_cell_length_c                   19.4932(12)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.570(2)
_cell_angle_gamma                90.00
_cell_volume                     5364.0(6)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4524
_cell_measurement_theta_min      4.534
_cell_measurement_theta_max      56.508

_exptl_crystal_description       prismatic
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.311
_exptl_crystal_size_mid          0.257
_exptl_crystal_size_min          0.205
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.325
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2232
_exptl_absorpt_coefficient_mu    0.178
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.77314
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   sadabs

_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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            15604
_diffrn_reflns_av_R_equivalents  0.0233
_diffrn_reflns_av_sigmaI/netI    0.0273
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         1.75
_diffrn_reflns_theta_max         25.50
_reflns_number_total             5002
_reflns_number_gt                3936
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0946P)²+5.2331P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5002
_refine_ls_number_parameters     358
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0710
_refine_ls_R_factor_gt           0.0581
_refine_ls_wR_factor_ref         0.1780
_refine_ls_wR_factor_gt          0.1653
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_restrained_S_all      1.019
_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
Cl1 Cl 0.40656(14) 0.80931(15) 0.25505(12) 0.2096(10) Uani 1 1 d . . .
N1 N 0.19350(11) 0.00518(10) 0.38775(9) 0.0414(4) Uani 1 1 d . . .
N2 N 0.26335(11) 0.02736(10) 0.51489(10) 0.0435(4) Uani 1 1 d . . .
O1 O 0.37795(13) 0.22393(12) 0.17664(12) 0.0797(6) Uani 1 1 d . . .
O2 O 0.45308(11) 0.11848(10) 0.16808(9) 0.0589(5) Uani 1 1 d . . .
C1 C 0.23659(13) -0.05685(11) 0.42083(11) 0.0408(5) Uani 1 1 d . . .
C2 C 0.23763(14) -0.12683(12) 0.39180(12) 0.0460(5) Uani 1 1 d . . .
H2 H 0.2097 -0.1354 0.3492 0.055 Uiso 1 1 calc R . .
C3 C 0.28044(16) -0.18411(13) 0.42661(14) 0.0535(6) Uani 1 1 d . . .
H3 H 0.2831 -0.2310 0.4067 0.064 Uiso 1 1 calc R . .
C4 C 0.31908(15) -0.17169(13) 0.49068(14) 0.0537(6) Uani 1 1 d . . .
H4 H 0.3481 -0.2103 0.5138 0.064 Uiso 1 1 calc R . .
C5 C 0.31533(14) -0.10279(12) 0.52102(13) 0.0474(5) Uani 1 1 d . . .
H5 H 0.3395 -0.0955 0.5651 0.057 Uiso 1 1 calc R . .
C6 C 0.27532(13) -0.04440(11) 0.48556(11) 0.0407(5) Uani 1 1 d . . .
C7 C 0.14252(13) 0.04558(11) 0.43573(11) 0.0385(5) Uani 1 1 d . . .
C8 C 0.17813(13) 0.05591(11) 0.49942(11) 0.0397(5) Uani 1 1 d . . .
C9 C 0.12899(13) 0.08841(11) 0.55325(11) 0.0410(5) Uani 1 1 d . . .
C10 C 0.16414(16) 0.09517(14) 0.62069(12) 0.0541(6) Uani 1 1 d . . .
H10 H 0.2206 0.0785 0.6313 0.065 Uiso 1 1 calc R . .
C11 C 0.11674(19) 0.12573(17) 0.67055(14) 0.0680(8) Uani 1 1 d . . .
H11 H 0.1409 0.1302 0.7150 0.082 Uiso 1 1 calc R . .
C12 C 0.03222(19) 0.15030(17) 0.65532(14) 0.0674(8) Uani 1 1 d . . .
H12 H -0.0001 0.1713 0.6896 0.081 Uiso 1 1 calc R . .
C13 C -0.00375(16) 0.14380(14) 0.59024(13) 0.0531(6) Uani 1 1 d . . .
H13 H -0.0605 0.1606 0.5809 0.064 Uiso 1 1 calc R . .
C14 C 0.04287(13) 0.11234(11) 0.53729(11) 0.0404(5) Uani 1 1 d . . .
C15 C 0.00489(13) 0.10214(11) 0.46834(11) 0.0386(5) Uani 1 1 d . . .
C16 C -0.08127(14) 0.12394(13) 0.44956(12) 0.0468(5) Uani 1 1 d . . .
H16 H -0.1147 0.1474 0.4818 0.056 Uiso 1 1 calc R . .
C17 C -0.11662(15) 0.11145(15) 0.38551(13) 0.0563(6) Uani 1 1 d . . .
H17 H -0.1733 0.1271 0.3742 0.068 Uiso 1 1 calc R . .
C18 C -0.06879(16) 0.07552(16) 0.33680(13) 0.0588(6) Uani 1 1 d . . .
H18 H -0.0937 0.0665 0.2932 0.071 Uiso 1 1 calc R . .
C19 C 0.01519(15) 0.05322(14) 0.35275(12) 0.0501(6) Uani 1 1 d . . .
H19 H 0.0469 0.0289 0.3199 0.060 Uiso 1 1 calc R . .
C20 C 0.05378(13) 0.06673(11) 0.41805(11) 0.0396(5) Uani 1 1 d . . .
C21 C 0.23950(13) 0.04369(12) 0.33792(10) 0.0400(5) Uani 1 1 d . . .
C22 C 0.30212(17) 0.00686(14) 0.30077(13) 0.0550(6) Uani 1 1 d . . .
H22 H 0.3121 -0.0435 0.3083 0.066 Uiso 1 1 calc R . .
C23 C 0.34919(17) 0.04383(14) 0.25336(13) 0.0554(6) Uani 1 1 d . . .
H23 H 0.3911 0.0182 0.2296 0.067 Uiso 1 1 calc R . .
C24 C 0.33568(14) 0.11815(13) 0.24013(11) 0.0452(5) Uani 1 1 d . . .
C25 C 0.27184(15) 0.15479(13) 0.27539(12) 0.0486(5) Uani 1 1 d . . .
H25 H 0.2609 0.2048 0.2664 0.058 Uiso 1 1 calc R . .
C26 C 0.22415(15) 0.11819(13) 0.32372(12) 0.0466(5) Uani 1 1 d . . .
H26 H 0.1816 0.1437 0.3468 0.056 Uiso 1 1 calc R . .
C27 C 0.38965(15) 0.16048(15) 0.19236(12) 0.0500(6) Uani 1 1 d . . .
C28 C 0.51225(17) 0.15301(18) 0.12214(14) 0.0666(8) Uani 1 1 d . . .
H28A H 0.4793 0.1784 0.0862 0.100 Uiso 1 1 calc R . .
H28B H 0.5482 0.1156 0.1024 0.100 Uiso 1 1 calc R . .
H28C H 0.5487 0.1880 0.1472 0.100 Uiso 1 1 calc R . .
C29 C 0.33352(13) 0.07749(12) 0.52980(11) 0.0437(5) Uani 1 1 d . . .
C30 C 0.32173(16) 0.15291(14) 0.52044(16) 0.0615(7) Uani 1 1 d . . .
H30 H 0.2684 0.1704 0.5024 0.074 Uiso 1 1 calc R . .
C31 C 0.38775(18) 0.20282(16) 0.53741(17) 0.0705(8) Uani 1 1 d . . .
H31 H 0.3780 0.2534 0.5313 0.085 Uiso 1 1 calc R . .
C32 C 0.46709(17) 0.17866(16) 0.56301(15) 0.0661(7) Uani 1 1 d . . .
H32 H 0.5113 0.2123 0.5749 0.079 Uiso 1 1 calc R . .
C33 C 0.48031(17) 0.10400(17) 0.57093(16) 0.0678(8) Uani 1 1 d . . .
H33 H 0.5346 0.0870 0.5876 0.081 Uiso 1 1 calc R . .
C34 C 0.41472(16) 0.05315(15) 0.55470(15) 0.0586(7) Uani 1 1 d . . .
H34 H 0.4252 0.0026 0.5605 0.070 Uiso 1 1 calc R . .
C35 C 0.5000 0.7558(5) 0.2500 0.205(5) Uani 1 2 d S . .
H35A H 0.4942 0.7240 0.2098 0.246 Uiso 0.50 1 calc PR . .
H35B H 0.5058 0.7240 0.2902 0.246 Uiso 0.50 1 calc PR . .


_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
Cl1 C35 1.731(5) . ?
N1 C21 1.407(3) . ?
N1 C1 1.435(3) . ?
N1 C7 1.442(3) . ?
N2 C8 1.422(3) . ?
N2 C29 1.423(3) . ?
N2 C6 1.427(3) . ?
O1 C27 1.193(3) . ?
O2 C27 1.334(3) . ?
O2 C28 1.443(3) . ?
C1 C2 1.381(3) . ?
C1 C6 1.388(3) . ?
C2 C3 1.383(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.376(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.376(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.385(3) . ?
C5 H5 0.9300 . ?
C7 C8 1.346(3) . ?
C7 C20 1.438(3) . ?
C8 C9 1.442(3) . ?
C9 C10 1.403(3) . ?
C9 C14 1.408(3) . ?
C10 C11 1.355(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.387(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.365(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.400(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.452(3) . ?
C15 C16 1.409(3) . ?
C15 C20 1.412(3) . ?
C16 C17 1.357(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.385(4) . ?
C17 H17 0.9300 . ?
C18 C19 1.369(3) . ?
C18 H18 0.9300 . ?
C19 C20 1.400(3) . ?
C19 H19 0.9300 . ?
C21 C26 1.387(3) . ?
C21 C22 1.395(3) . ?
C22 C23 1.370(3) . ?
C22 H22 0.9300 . ?
C23 C24 1.376(3) . ?
C23 H23 0.9300 . ?
C24 C25 1.386(3) . ?
C24 C27 1.483(3) . ?
C25 C26 1.384(3) . ?
C25 H25 0.9300 . ?
C26 H26 0.9300 . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?
C29 C30 1.380(3) . ?
C29 C34 1.385(3) . ?
C30 C31 1.381(4) . ?
C30 H30 0.9300 . ?
C31 C32 1.363(4) . ?
C31 H31 0.9300 . ?
C32 C33 1.366(4) . ?
C32 H32 0.9300 . ?
C33 C34 1.384(4) . ?
C33 H33 0.9300 . ?
C34 H34 0.9300 . ?
C35 Cl1 1.731(5) 2_655 ?
C35 H35A 0.9700 . ?
C35 H35B 0.9700 . ?

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
C21 N1 C1 117.33(16) . . ?
C21 N1 C7 120.10(17) . . ?
C1 N1 C7 110.62(16) . . ?
C8 N2 C29 119.44(17) . . ?
C8 N2 C6 112.02(17) . . ?
C29 N2 C6 123.10(17) . . ?
C27 O2 C28 117.6(2) . . ?
C2 C1 C6 120.5(2) . . ?
C2 C1 N1 122.6(2) . . ?
C6 C1 N1 116.88(19) . . ?
C1 C2 C3 119.5(2) . . ?
C1 C2 H2 120.3 . . ?
C3 C2 H2 120.3 . . ?
C4 C3 C2 119.9(2) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C5 C4 C3 120.8(2) . . ?
C5 C4 H4 119.6 . . ?
C3 C4 H4 119.6 . . ?
C4 C5 C6 119.7(2) . . ?
C4 C5 H5 120.2 . . ?
C6 C5 H5 120.2 . . ?
C5 C6 C1 119.5(2) . . ?
C5 C6 N2 123.2(2) . . ?
C1 C6 N2 116.93(18) . . ?
C8 C7 C20 121.58(19) . . ?
C8 C7 N1 117.34(18) . . ?
C20 C7 N1 120.75(18) . . ?
C7 C8 N2 118.39(19) . . ?
C7 C8 C9 121.61(19) . . ?
N2 C8 C9 119.71(19) . . ?
C10 C9 C14 119.8(2) . . ?
C10 C9 C8 121.8(2) . . ?
C14 C9 C8 118.48(19) . . ?
C11 C10 C9 120.8(2) . . ?
C11 C10 H10 119.6 . . ?
C9 C10 H10 119.6 . . ?
C10 C11 C12 120.0(2) . . ?
C10 C11 H11 120.0 . . ?
C12 C11 H11 120.0 . . ?
C13 C12 C11 120.3(2) . . ?
C13 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
C12 C13 C14 121.5(2) . . ?
C12 C13 H13 119.3 . . ?
C14 C13 H13 119.3 . . ?
C13 C14 C9 117.6(2) . . ?
C13 C14 C15 122.5(2) . . ?
C9 C14 C15 119.86(19) . . ?
C16 C15 C20 117.7(2) . . ?
C16 C15 C14 122.47(19) . . ?
C20 C15 C14 119.81(18) . . ?
C17 C16 C15 121.5(2) . . ?
C17 C16 H16 119.2 . . ?
C15 C16 H16 119.2 . . ?
C16 C17 C18 120.5(2) . . ?
C16 C17 H17 119.8 . . ?
C18 C17 H17 119.8 . . ?
C19 C18 C17 120.1(2) . . ?
C19 C18 H18 120.0 . . ?
C17 C18 H18 120.0 . . ?
C18 C19 C20 120.6(2) . . ?
C18 C19 H19 119.7 . . ?
C20 C19 H19 119.7 . . ?
C19 C20 C15 119.63(19) . . ?
C19 C20 C7 121.84(19) . . ?
C15 C20 C7 118.53(19) . . ?
C26 C21 C22 118.0(2) . . ?
C26 C21 N1 121.89(19) . . ?
C22 C21 N1 120.08(19) . . ?
C23 C22 C21 121.0(2) . . ?
C23 C22 H22 119.5 . . ?
C21 C22 H22 119.5 . . ?
C22 C23 C24 121.3(2) . . ?
C22 C23 H23 119.4 . . ?
C24 C23 H23 119.4 . . ?
C23 C24 C25 118.2(2) . . ?
C23 C24 C27 122.3(2) . . ?
C25 C24 C27 119.5(2) . . ?
C26 C25 C24 121.1(2) . . ?
C26 C25 H25 119.5 . . ?
C24 C25 H25 119.5 . . ?
C25 C26 C21 120.4(2) . . ?
C25 C26 H26 119.8 . . ?
C21 C26 H26 119.8 . . ?
O1 C27 O2 123.6(2) . . ?
O1 C27 C24 124.8(2) . . ?
O2 C27 C24 111.5(2) . . ?
O2 C28 H28A 109.5 . . ?
O2 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
O2 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C30 C29 C34 117.8(2) . . ?
C30 C29 N2 120.2(2) . . ?
C34 C29 N2 121.9(2) . . ?
C29 C30 C31 121.2(2) . . ?
C29 C30 H30 119.4 . . ?
C31 C30 H30 119.4 . . ?
C32 C31 C30 120.7(3) . . ?
C32 C31 H31 119.6 . . ?
C30 C31 H31 119.6 . . ?
C31 C32 C33 118.7(2) . . ?
C31 C32 H32 120.7 . . ?
C33 C32 H32 120.7 . . ?
C32 C33 C34 121.4(3) . . ?
C32 C33 H33 119.3 . . ?
C34 C33 H33 119.3 . . ?
C33 C34 C29 120.1(2) . . ?
C33 C34 H34 120.0 . . ?
C29 C34 H34 120.0 . . ?
Cl1 C35 Cl1 112.4(5) . 2_655 ?
Cl1 C35 H35A 109.1 . . ?
Cl1 C35 H35A 109.1 2_655 . ?
Cl1 C35 H35B 109.1 . . ?
Cl1 C35 H35B 109.1 2_655 . ?
H35A C35 H35B 107.9 . . ?

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
C21 N1 C1 C2 -82.6(3) . . . . ?
C7 N1 C1 C2 134.5(2) . . . . ?
C21 N1 C1 C6 99.7(2) . . . . ?
C7 N1 C1 C6 -43.2(2) . . . . ?
C6 C1 C2 C3 -2.4(3) . . . . ?
N1 C1 C2 C3 -179.98(19) . . . . ?
C1 C2 C3 C4 2.2(3) . . . . ?
C2 C3 C4 C5 0.4(3) . . . . ?
C3 C4 C5 C6 -2.7(3) . . . . ?
C4 C5 C6 C1 2.4(3) . . . . ?
C4 C5 C6 N2 175.6(2) . . . . ?
C2 C1 C6 C5 0.1(3) . . . . ?
N1 C1 C6 C5 177.82(18) . . . . ?
C2 C1 C6 N2 -173.51(18) . . . . ?
N1 C1 C6 N2 4.2(3) . . . . ?
C8 N2 C6 C5 -135.7(2) . . . . ?
C29 N2 C6 C5 70.6(3) . . . . ?
C8 N2 C6 C1 37.6(3) . . . . ?
C29 N2 C6 C1 -116.1(2) . . . . ?
C21 N1 C7 C8 -100.8(2) . . . . ?
C1 N1 C7 C8 41.0(2) . . . . ?
C21 N1 C7 C20 85.7(2) . . . . ?
C1 N1 C7 C20 -132.56(19) . . . . ?
C20 C7 C8 N2 174.20(18) . . . . ?
N1 C7 C8 N2 0.7(3) . . . . ?
C20 C7 C8 C9 0.3(3) . . . . ?
N1 C7 C8 C9 -173.18(18) . . . . ?
C29 N2 C8 C7 114.1(2) . . . . ?
C6 N2 C8 C7 -40.7(3) . . . . ?
C29 N2 C8 C9 -71.8(3) . . . . ?
C6 N2 C8 C9 133.4(2) . . . . ?
C7 C8 C9 C10 176.1(2) . . . . ?
N2 C8 C9 C10 2.3(3) . . . . ?
C7 C8 C9 C14 -2.5(3) . . . . ?
N2 C8 C9 C14 -176.39(18) . . . . ?
C14 C9 C10 C11 -1.2(4) . . . . ?
C8 C9 C10 C11 -179.8(2) . . . . ?
C9 C10 C11 C12 0.5(5) . . . . ?
C10 C11 C12 C13 0.1(5) . . . . ?
C11 C12 C13 C14 0.1(4) . . . . ?
C12 C13 C14 C9 -0.9(4) . . . . ?
C12 C13 C14 C15 177.5(2) . . . . ?
C10 C9 C14 C13 1.4(3) . . . . ?
C8 C9 C14 C13 -179.95(19) . . . . ?
C10 C9 C14 C15 -177.0(2) . . . . ?
C8 C9 C14 C15 1.6(3) . . . . ?
C13 C14 C15 C16 0.7(3) . . . . ?
C9 C14 C15 C16 179.1(2) . . . . ?
C13 C14 C15 C20 -176.9(2) . . . . ?
C9 C14 C15 C20 1.5(3) . . . . ?
C20 C15 C16 C17 0.1(3) . . . . ?
C14 C15 C16 C17 -177.6(2) . . . . ?
C15 C16 C17 C18 1.0(4) . . . . ?
C16 C17 C18 C19 -0.9(4) . . . . ?
C17 C18 C19 C20 -0.3(4) . . . . ?
C18 C19 C20 C15 1.5(3) . . . . ?
C18 C19 C20 C7 -178.5(2) . . . . ?
C16 C15 C20 C19 -1.3(3) . . . . ?
C14 C15 C20 C19 176.39(19) . . . . ?
C16 C15 C20 C7 178.59(19) . . . . ?
C14 C15 C20 C7 -3.7(3) . . . . ?
C8 C7 C20 C19 -177.2(2) . . . . ?
N1 C7 C20 C19 -4.0(3) . . . . ?
C8 C7 C20 C15 2.9(3) . . . . ?
N1 C7 C20 C15 176.10(17) . . . . ?
C1 N1 C21 C26 -152.6(2) . . . . ?
C7 N1 C21 C26 -13.3(3) . . . . ?
C1 N1 C21 C22 27.9(3) . . . . ?
C7 N1 C21 C22 167.2(2) . . . . ?
C26 C21 C22 C23 2.2(4) . . . . ?
N1 C21 C22 C23 -178.3(2) . . . . ?
C21 C22 C23 C24 -0.8(4) . . . . ?
C22 C23 C24 C25 -1.0(4) . . . . ?
C22 C23 C24 C27 176.0(2) . . . . ?
C23 C24 C25 C26 1.4(3) . . . . ?
C27 C24 C25 C26 -175.7(2) . . . . ?
C24 C25 C26 C21 0.1(3) . . . . ?
C22 C21 C26 C25 -1.8(3) . . . . ?
N1 C21 C26 C25 178.7(2) . . . . ?
C28 O2 C27 O1 2.2(4) . . . . ?
C28 O2 C27 C24 -178.5(2) . . . . ?
C23 C24 C27 O1 176.2(3) . . . . ?
C25 C24 C27 O1 -6.8(4) . . . . ?
C23 C24 C27 O2 -3.1(3) . . . . ?
C25 C24 C27 O2 173.9(2) . . . . ?
C8 N2 C29 C30 -8.6(3) . . . . ?
C6 N2 C29 C30 143.3(2) . . . . ?
C8 N2 C29 C34 170.6(2) . . . . ?
C6 N2 C29 C34 -37.6(3) . . . . ?
C34 C29 C30 C31 -2.1(4) . . . . ?
N2 C29 C30 C31 177.1(3) . . . . ?
C29 C30 C31 C32 1.0(5) . . . . ?
C30 C31 C32 C33 0.6(5) . . . . ?
C31 C32 C33 C34 -1.1(5) . . . . ?
C32 C33 C34 C29 0.0(5) . . . . ?
C30 C29 C34 C33 1.5(4) . . . . ?
N2 C29 C34 C33 -177.6(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.50
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.491
_refine_diff_density_min         -0.650
_refine_diff_density_rms         0.046
####################################################################### 
# 
# 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_cd211425
_database_code_depnum_ccdc_archive 'CCDC 888998'
_audit_update_record             
;
2012-06-28 deposited with the CCDC.
2016-03-16 downloaded from the CCDC.
;
#TrackingRef '12243_web_deposit_cif_file_1_ZhiyunZhang_1340861247.cd211425.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C36 H24 N2'
_chemical_formula_weight         484.57

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           Monoclinic
_symmetry_space_group_name_H-M   C2/c

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

_cell_length_a                   14.0547(18)
_cell_length_b                   19.251(3)
_cell_length_c                   18.410(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.832(3)
_cell_angle_gamma                90.00
_cell_volume                     4980.7(11)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3813
_cell_measurement_theta_min      4.425
_cell_measurement_theta_max      49.701

_exptl_crystal_description       prismatic
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.309
_exptl_crystal_size_mid          0.238
_exptl_crystal_size_min          0.197
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.292
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2032
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.84202
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   sadabs

_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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            13435
_diffrn_reflns_av_R_equivalents  0.0210
_diffrn_reflns_av_sigmaI/netI    0.0259
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.10
_diffrn_reflns_theta_max         26.00
_reflns_number_total             4891
_reflns_number_gt                3692
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0569P)²+1.2108P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4891
_refine_ls_number_parameters     343
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0549
_refine_ls_R_factor_gt           0.0398
_refine_ls_wR_factor_ref         0.1145
_refine_ls_wR_factor_gt          0.1038
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_restrained_S_all      1.023
_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 0.72504(7) 0.47311(6) 0.04386(6) 0.0421(3) Uani 1 1 d . . .
N2 N 0.68771(8) 0.38016(6) 0.15427(6) 0.0462(3) Uani 1 1 d . . .
C1 C 0.74718(9) 0.49234(7) 0.11766(7) 0.0407(3) Uani 1 1 d . . .
C2 C 0.78525(10) 0.55704(8) 0.13461(8) 0.0480(3) Uani 1 1 d . . .
H2 H 0.8012 0.5876 0.0976 0.058 Uiso 1 1 calc R . .
C3 C 0.79953(10) 0.57613(8) 0.20654(8) 0.0546(4) Uani 1 1 d . . .
H3 H 0.8269 0.6189 0.2176 0.065 Uiso 1 1 calc R . .
C4 C 0.77355(11) 0.53227(8) 0.26158(8) 0.0534(4) Uani 1 1 d . . .
H4 H 0.7814 0.5459 0.3097 0.064 Uiso 1 1 calc R . .
C5 C 0.73574(11) 0.46788(7) 0.24536(8) 0.0499(4) Uani 1 1 d . . .
H5 H 0.7174 0.4384 0.2826 0.060 Uiso 1 1 calc R . .
C6 C 0.72507(9) 0.44700(7) 0.17354(7) 0.0429(3) Uani 1 1 d . . .
C7 C 0.62560(9) 0.38263(7) 0.09194(7) 0.0428(3) Uani 1 1 d . . .
C8 C 0.64565(9) 0.42691(7) 0.03698(7) 0.0406(3) Uani 1 1 d . . .
C9 C 0.58359(9) 0.43157(7) -0.02612(7) 0.0422(3) Uani 1 1 d . . .
C10 C 0.59922(10) 0.47955(8) -0.08179(7) 0.0491(3) Uani 1 1 d . . .
H10 H 0.6503 0.5101 -0.0780 0.059 Uiso 1 1 calc R . .
C11 C 0.54038(11) 0.48224(9) -0.14205(8) 0.0557(4) Uani 1 1 d . . .
H11 H 0.5513 0.5150 -0.1781 0.067 Uiso 1 1 calc R . .
C12 C 0.46497(11) 0.43642(9) -0.14913(8) 0.0578(4) Uani 1 1 d . . .
H12 H 0.4263 0.4375 -0.1905 0.069 Uiso 1 1 calc R . .
C13 C 0.44754(10) 0.38972(8) -0.09530(9) 0.0558(4) Uani 1 1 d . . .
H13 H 0.3966 0.3593 -0.1007 0.067 Uiso 1 1 calc R . .
C14 C 0.50429(9) 0.38615(7) -0.03179(8) 0.0457(3) Uani 1 1 d . . .
C15 C 0.48126(10) 0.34090(7) 0.02857(8) 0.0482(3) Uani 1 1 d . . .
C16 C 0.40037(11) 0.29792(8) 0.02880(10) 0.0644(4) Uani 1 1 d . . .
H16 H 0.3616 0.2958 -0.0125 0.077 Uiso 1 1 calc R . .
C17 C 0.37738(13) 0.25925(9) 0.08814(11) 0.0733(5) Uani 1 1 d . . .
H17 H 0.3238 0.2309 0.0866 0.088 Uiso 1 1 calc R . .
C18 C 0.43338(13) 0.26198(9) 0.15055(10) 0.0706(5) Uani 1 1 d . . .
H18 H 0.4164 0.2366 0.1914 0.085 Uiso 1 1 calc R . .
C19 C 0.51371(12) 0.30200(8) 0.15207(9) 0.0586(4) Uani 1 1 d . . .
H19 H 0.5516 0.3031 0.1939 0.070 Uiso 1 1 calc R . .
C20 C 0.53982(10) 0.34137(7) 0.09157(8) 0.0468(3) Uani 1 1 d . . .
C21 C 0.80682(9) 0.45801(7) -0.00157(7) 0.0450(3) Uani 1 1 d . . .
C22 C 0.84362(10) 0.39249(8) -0.00261(8) 0.0537(4) Uani 1 1 d . . .
H22 H 0.8155 0.3580 0.0252 0.064 Uiso 1 1 calc R . .
C23 C 0.92273(11) 0.37576(9) -0.04449(9) 0.0642(4) Uani 1 1 d . . .
H23 H 0.9459 0.3305 -0.0451 0.077 Uiso 1 1 calc R . .
C24 C 0.96507(11) 0.42556(10) -0.08393(9) 0.0663(5) Uani 1 1 d . . .
H24 H 1.0177 0.4142 -0.1116 0.080 Uiso 1 1 calc R . .
C25 C 0.93124(10) 0.49472(9) -0.08412(8) 0.0568(4) Uani 1 1 d . . .
C26 C 0.84897(10) 0.51131(8) -0.04291(7) 0.0484(3) Uani 1 1 d . . .
C27 C 0.81327(11) 0.58020(9) -0.04718(8) 0.0574(4) Uani 1 1 d . . .
H27 H 0.7580 0.5918 -0.0228 0.069 Uiso 1 1 calc R . .
C28 C 0.85902(14) 0.62932(10) -0.08647(9) 0.0722(5) Uani 1 1 d . . .
H28 H 0.8349 0.6743 -0.0886 0.087 Uiso 1 1 calc R . .
C29 C 0.94270(14) 0.61281(12) -0.12412(11) 0.0829(6) Uani 1 1 d . . .
H29 H 0.9746 0.6473 -0.1494 0.099 Uiso 1 1 calc R . .
C30 C 0.97650(13) 0.54748(12) -0.12357(9) 0.0750(5) Uani 1 1 d . . .
H30 H 1.0308 0.5370 -0.1497 0.090 Uiso 1 1 calc R . .
C31 C 0.74424(10) 0.31973(7) 0.16661(8) 0.0462(3) Uani 1 1 d . . .
C32 C 0.80889(13) 0.31606(8) 0.22374(9) 0.0675(5) Uani 1 1 d . . .
H32 H 0.8168 0.3540 0.2545 0.081 Uiso 1 1 calc R . .
C33 C 0.86199(14) 0.25650(9) 0.23570(10) 0.0784(5) Uani 1 1 d . . .
H33 H 0.9047 0.2550 0.2747 0.094 Uiso 1 1 calc R . .
C34 C 0.85293(14) 0.20025(9) 0.19161(11) 0.0733(5) Uani 1 1 d . . .
H34 H 0.8888 0.1604 0.2002 0.088 Uiso 1 1 calc R . .
C35 C 0.79057(14) 0.20337(9) 0.13488(11) 0.0740(5) Uani 1 1 d . . .
H35 H 0.7841 0.1653 0.1041 0.089 Uiso 1 1 calc R . .
C36 C 0.73639(12) 0.26209(8) 0.12185(9) 0.0616(4) Uani 1 1 d . . .
H36 H 0.6941 0.2629 0.0825 0.074 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 C8 1.4309(16) . ?
N1 C1 1.4379(16) . ?
N1 C21 1.4605(17) . ?
N2 C31 1.4252(17) . ?
N2 C7 1.4324(17) . ?
N2 C6 1.4324(17) . ?
C1 C6 1.3879(19) . ?
C1 C2 1.3893(19) . ?
C2 C3 1.386(2) . ?
C2 H2 0.9300 . ?
C3 C4 1.373(2) . ?
C3 H3 0.9300 . ?
C4 C5 1.380(2) . ?
C4 H4 0.9300 . ?
C5 C6 1.3881(18) . ?
C5 H5 0.9300 . ?
C7 C8 1.3558(19) . ?
C7 C20 1.4436(19) . ?
C8 C9 1.4453(18) . ?
C9 C10 1.3994(19) . ?
C9 C14 1.4192(19) . ?
C10 C11 1.375(2) . ?
C10 H10 0.9300 . ?
C11 C12 1.384(2) . ?
C11 H11 0.9300 . ?
C12 C13 1.363(2) . ?
C12 H12 0.9300 . ?
C13 C14 1.4074(19) . ?
C13 H13 0.9300 . ?
C14 C15 1.452(2) . ?
C15 C16 1.406(2) . ?
C15 C20 1.4124(19) . ?
C16 C17 1.365(2) . ?
C16 H16 0.9300 . ?
C17 C18 1.384(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.367(2) . ?
C18 H18 0.9300 . ?
C19 C20 1.401(2) . ?
C19 H19 0.9300 . ?
C21 C22 1.364(2) . ?
C21 C26 1.413(2) . ?
C22 C23 1.400(2) . ?
C22 H22 0.9300 . ?
C23 C24 1.346(2) . ?
C23 H23 0.9300 . ?
C24 C25 1.414(2) . ?
C24 H24 0.9300 . ?
C25 C30 1.406(2) . ?
C25 C26 1.428(2) . ?
C26 C27 1.420(2) . ?
C27 C28 1.358(2) . ?
C27 H27 0.9300 . ?
C28 C29 1.410(3) . ?
C28 H28 0.9300 . ?
C29 C30 1.344(3) . ?
C29 H29 0.9300 . ?
C30 H30 0.9300 . ?
C31 C32 1.382(2) . ?
C31 C36 1.386(2) . ?
C32 C33 1.384(2) . ?
C32 H32 0.9300 . ?
C33 C34 1.358(2) . ?
C33 H33 0.9300 . ?
C34 C35 1.355(2) . ?
C34 H34 0.9300 . ?
C35 C36 1.382(2) . ?
C35 H35 0.9300 . ?
C36 H36 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
C8 N1 C1 113.67(10) . . ?
C8 N1 C21 116.41(10) . . ?
C1 N1 C21 115.52(10) . . ?
C31 N2 C7 119.12(10) . . ?
C31 N2 C6 119.49(11) . . ?
C7 N2 C6 112.68(10) . . ?
C6 C1 C2 119.14(12) . . ?
C6 C1 N1 119.39(11) . . ?
C2 C1 N1 121.37(12) . . ?
C3 C2 C1 120.15(14) . . ?
C3 C2 H2 119.9 . . ?
C1 C2 H2 119.9 . . ?
C4 C3 C2 120.39(14) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C3 C4 C5 119.91(13) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C4 C5 C6 120.16(14) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C1 C6 C5 120.11(12) . . ?
C1 C6 N2 117.81(11) . . ?
C5 C6 N2 122.03(12) . . ?
C8 C7 N2 119.20(12) . . ?
C8 C7 C20 121.67(12) . . ?
N2 C7 C20 118.99(12) . . ?
C7 C8 N1 119.67(12) . . ?
C7 C8 C9 120.61(12) . . ?
N1 C8 C9 119.56(12) . . ?
C10 C9 C14 118.96(12) . . ?
C10 C9 C8 122.02(12) . . ?
C14 C9 C8 119.02(12) . . ?
C11 C10 C9 121.12(14) . . ?
C11 C10 H10 119.4 . . ?
C9 C10 H10 119.4 . . ?
C10 C11 C12 120.19(15) . . ?
C10 C11 H11 119.9 . . ?
C12 C11 H11 119.9 . . ?
C13 C12 C11 119.84(14) . . ?
C13 C12 H12 120.1 . . ?
C11 C12 H12 120.1 . . ?
C12 C13 C14 122.04(14) . . ?
C12 C13 H13 119.0 . . ?
C14 C13 H13 119.0 . . ?
C13 C14 C9 117.78(13) . . ?
C13 C14 C15 122.35(13) . . ?
C9 C14 C15 119.78(12) . . ?
C16 C15 C20 117.57(14) . . ?
C16 C15 C14 122.99(14) . . ?
C20 C15 C14 119.39(12) . . ?
C17 C16 C15 121.62(16) . . ?
C17 C16 H16 119.2 . . ?
C15 C16 H16 119.2 . . ?
C16 C17 C18 120.35(16) . . ?
C16 C17 H17 119.8 . . ?
C18 C17 H17 119.8 . . ?
C19 C18 C17 119.87(17) . . ?
C19 C18 H18 120.1 . . ?
C17 C18 H18 120.1 . . ?
C18 C19 C20 120.98(16) . . ?
C18 C19 H19 119.5 . . ?
C20 C19 H19 119.5 . . ?
C19 C20 C15 119.55(13) . . ?
C19 C20 C7 121.50(13) . . ?
C15 C20 C7 118.95(13) . . ?
C22 C21 C26 120.14(13) . . ?
C22 C21 N1 119.60(13) . . ?
C26 C21 N1 120.24(12) . . ?
C21 C22 C23 121.67(16) . . ?
C21 C22 H22 119.2 . . ?
C23 C22 H22 119.2 . . ?
C24 C23 C22 119.61(16) . . ?
C24 C23 H23 120.2 . . ?
C22 C23 H23 120.2 . . ?
C23 C24 C25 121.38(15) . . ?
C23 C24 H24 119.3 . . ?
C25 C24 H24 119.3 . . ?
C30 C25 C24 121.81(16) . . ?
C30 C25 C26 119.25(17) . . ?
C24 C25 C26 118.94(15) . . ?
C21 C26 C27 123.89(13) . . ?
C21 C26 C25 118.22(14) . . ?
C27 C26 C25 117.87(14) . . ?
C28 C27 C26 120.68(16) . . ?
C28 C27 H27 119.7 . . ?
C26 C27 H27 119.7 . . ?
C27 C28 C29 120.63(19) . . ?
C27 C28 H28 119.7 . . ?
C29 C28 H28 119.7 . . ?
C30 C29 C28 120.29(18) . . ?
C30 C29 H29 119.9 . . ?
C28 C29 H29 119.9 . . ?
C29 C30 C25 121.15(18) . . ?
C29 C30 H30 119.4 . . ?
C25 C30 H30 119.4 . . ?
C32 C31 C36 117.23(13) . . ?
C32 C31 N2 121.47(12) . . ?
C36 C31 N2 121.30(13) . . ?
C31 C32 C33 120.71(15) . . ?
C31 C32 H32 119.6 . . ?
C33 C32 H32 119.6 . . ?
C34 C33 C32 121.32(16) . . ?
C34 C33 H33 119.3 . . ?
C32 C33 H33 119.3 . . ?
C35 C34 C33 118.64(15) . . ?
C35 C34 H34 120.7 . . ?
C33 C34 H34 120.7 . . ?
C34 C35 C36 121.24(16) . . ?
C34 C35 H35 119.4 . . ?
C36 C35 H35 119.4 . . ?
C35 C36 C31 120.86(15) . . ?
C35 C36 H36 119.6 . . ?
C31 C36 H36 119.6 . . ?

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
C8 N1 C1 C6 27.94(16) . . . . ?
C21 N1 C1 C6 -110.43(13) . . . . ?
C8 N1 C1 C2 -148.30(12) . . . . ?
C21 N1 C1 C2 73.33(16) . . . . ?
C6 C1 C2 C3 -0.91(19) . . . . ?
N1 C1 C2 C3 175.34(12) . . . . ?
C1 C2 C3 C4 -2.0(2) . . . . ?
C2 C3 C4 C5 2.0(2) . . . . ?
C3 C4 C5 C6 0.8(2) . . . . ?
C2 C1 C6 C5 3.77(19) . . . . ?
N1 C1 C6 C5 -172.56(12) . . . . ?
C2 C1 C6 N2 -178.78(12) . . . . ?
N1 C1 C6 N2 4.90(17) . . . . ?
C4 C5 C6 C1 -3.8(2) . . . . ?
C4 C5 C6 N2 178.89(13) . . . . ?
C31 N2 C6 C1 110.65(14) . . . . ?
C7 N2 C6 C1 -36.72(16) . . . . ?
C31 N2 C6 C5 -71.94(17) . . . . ?
C7 N2 C6 C5 140.68(13) . . . . ?
C31 N2 C7 C8 -111.01(14) . . . . ?
C6 N2 C7 C8 36.50(16) . . . . ?
C31 N2 C7 C20 73.22(16) . . . . ?
C6 N2 C7 C20 -139.27(12) . . . . ?
N2 C7 C8 N1 -3.57(18) . . . . ?
C20 C7 C8 N1 172.08(11) . . . . ?
N2 C7 C8 C9 -178.93(11) . . . . ?
C20 C7 C8 C9 -3.28(19) . . . . ?
C1 N1 C8 C7 -28.79(16) . . . . ?
C21 N1 C8 C7 109.20(14) . . . . ?
C1 N1 C8 C9 146.62(11) . . . . ?
C21 N1 C8 C9 -75.40(15) . . . . ?
C7 C8 C9 C10 176.22(12) . . . . ?
N1 C8 C9 C10 0.85(18) . . . . ?
C7 C8 C9 C14 -3.71(18) . . . . ?
N1 C8 C9 C14 -179.07(11) . . . . ?
C14 C9 C10 C11 -1.3(2) . . . . ?
C8 C9 C10 C11 178.73(12) . . . . ?
C9 C10 C11 C12 -1.0(2) . . . . ?
C10 C11 C12 C13 1.7(2) . . . . ?
C11 C12 C13 C14 -0.1(2) . . . . ?
C12 C13 C14 C9 -2.2(2) . . . . ?
C12 C13 C14 C15 174.38(14) . . . . ?
C10 C9 C14 C13 2.85(18) . . . . ?
C8 C9 C14 C13 -177.22(12) . . . . ?
C10 C9 C14 C15 -173.80(12) . . . . ?
C8 C9 C14 C15 6.13(18) . . . . ?
C13 C14 C15 C16 -0.8(2) . . . . ?
C9 C14 C15 C16 175.70(13) . . . . ?
C13 C14 C15 C20 -178.17(13) . . . . ?
C9 C14 C15 C20 -1.68(19) . . . . ?
C20 C15 C16 C17 1.6(2) . . . . ?
C14 C15 C16 C17 -175.79(15) . . . . ?
C15 C16 C17 C18 0.6(3) . . . . ?
C16 C17 C18 C19 -2.0(3) . . . . ?
C17 C18 C19 C20 1.0(3) . . . . ?
C18 C19 C20 C15 1.3(2) . . . . ?
C18 C19 C20 C7 -178.60(14) . . . . ?
C16 C15 C20 C19 -2.6(2) . . . . ?
C14 C15 C20 C19 174.94(13) . . . . ?
C16 C15 C20 C7 177.36(13) . . . . ?
C14 C15 C20 C7 -5.11(19) . . . . ?
C8 C7 C20 C19 -172.31(13) . . . . ?
N2 C7 C20 C19 3.35(19) . . . . ?
C8 C7 C20 C15 7.74(19) . . . . ?
N2 C7 C20 C15 -176.60(12) . . . . ?
C8 N1 C21 C22 -50.01(17) . . . . ?
C1 N1 C21 C22 87.20(15) . . . . ?
C8 N1 C21 C26 131.45(13) . . . . ?
C1 N1 C21 C26 -91.34(14) . . . . ?
C26 C21 C22 C23 -0.6(2) . . . . ?
N1 C21 C22 C23 -179.10(13) . . . . ?
C21 C22 C23 C24 1.2(2) . . . . ?
C22 C23 C24 C25 -0.1(2) . . . . ?
C23 C24 C25 C30 178.26(15) . . . . ?
C23 C24 C25 C26 -1.6(2) . . . . ?
C22 C21 C26 C27 177.52(13) . . . . ?
N1 C21 C26 C27 -3.9(2) . . . . ?
C22 C21 C26 C25 -1.12(19) . . . . ?
N1 C21 C26 C25 177.41(11) . . . . ?
C30 C25 C26 C21 -177.69(13) . . . . ?
C24 C25 C26 C21 2.2(2) . . . . ?
C30 C25 C26 C27 3.6(2) . . . . ?
C24 C25 C26 C27 -176.57(13) . . . . ?
C21 C26 C27 C28 178.19(14) . . . . ?
C25 C26 C27 C28 -3.2(2) . . . . ?
C26 C27 C28 C29 0.3(2) . . . . ?
C27 C28 C29 C30 2.3(3) . . . . ?
C28 C29 C30 C25 -1.8(3) . . . . ?
C24 C25 C30 C29 179.00(16) . . . . ?
C26 C25 C30 C29 -1.2(2) . . . . ?
C7 N2 C31 C32 176.61(14) . . . . ?
C6 N2 C31 C32 31.3(2) . . . . ?
C7 N2 C31 C36 -3.6(2) . . . . ?
C6 N2 C31 C36 -148.88(15) . . . . ?
C36 C31 C32 C33 -1.0(3) . . . . ?
N2 C31 C32 C33 178.84(16) . . . . ?
C31 C32 C33 C34 0.5(3) . . . . ?
C32 C33 C34 C35 0.2(3) . . . . ?
C33 C34 C35 C36 -0.5(3) . . . . ?
C34 C35 C36 C31 0.0(3) . . . . ?
C32 C31 C36 C35 0.7(3) . . . . ?
N2 C31 C36 C35 -179.08(15) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.181
_refine_diff_density_min         -0.145
_refine_diff_density_rms         0.030
####################################################################### 
# 
# 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_cd21252
_database_code_depnum_ccdc_archive 'CCDC 888999'
_audit_update_record             
;
2012-06-28 deposited with the CCDC.
2016-03-16 downloaded from the CCDC.
;
#TrackingRef '12244_web_deposit_cif_file_2_ZhiyunZhang_1340861247.cd21252.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C42 H26 N2'
_chemical_formula_weight         558.65

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           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/n

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

_cell_length_a                   11.4684(6)
_cell_length_b                   18.0050(9)
_cell_length_c                   13.8450(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.9890(10)
_cell_angle_gamma                90.00
_cell_volume                     2854.9(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4545
_cell_measurement_theta_min      4.490
_cell_measurement_theta_max      51.020

_exptl_crystal_description       prismatic
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.321
_exptl_crystal_size_mid          0.212
_exptl_crystal_size_min          0.156
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.300
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1168
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.58903
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   sadabs

_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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            17144
_diffrn_reflns_av_R_equivalents  0.0235
_diffrn_reflns_av_sigmaI/netI    0.0256
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.86
_diffrn_reflns_theta_max         26.00
_reflns_number_total             5607
_reflns_number_gt                3922
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0698P)²+0.3621P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5607
_refine_ls_number_parameters     397
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0703
_refine_ls_R_factor_gt           0.0486
_refine_ls_wR_factor_ref         0.1407
_refine_ls_wR_factor_gt          0.1257
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_restrained_S_all      1.023
_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 0.70601(13) 0.03770(7) 0.70359(9) 0.0600(4) Uani 1 1 d . . .
N2 N 0.76415(13) 0.14648(7) 0.57526(10) 0.0626(4) Uani 1 1 d . . .
C1 C 0.68565(16) 0.11392(9) 0.72760(12) 0.0610(4) Uani 1 1 d . . .
C2 C 0.63814(19) 0.13499(11) 0.81374(14) 0.0776(6) Uani 1 1 d . . .
H2 H 0.6245 0.0995 0.8606 0.093 Uiso 1 1 calc R . .
C3 C 0.6111(2) 0.20859(12) 0.82998(16) 0.0907(7) Uani 1 1 d . . .
H3 H 0.5810 0.2224 0.8884 0.109 Uiso 1 1 calc R . .
C4 C 0.6282(2) 0.26150(11) 0.76085(17) 0.0901(7) Uani 1 1 d . . .
H4 H 0.6074 0.3106 0.7717 0.108 Uiso 1 1 calc R . .
C5 C 0.67604(19) 0.24193(10) 0.67579(14) 0.0763(5) Uani 1 1 d . . .
H5 H 0.6866 0.2775 0.6284 0.092 Uiso 1 1 calc R . .
C6 C 0.70878(16) 0.16851(9) 0.66061(12) 0.0625(5) Uani 1 1 d . . .
C7 C 0.69586(15) 0.02278(9) 0.60212(12) 0.0564(4) Uani 1 1 d . . .
C8 C 0.72027(15) 0.07709(9) 0.53860(12) 0.0577(4) Uani 1 1 d . . .
C9 C 0.69752(15) 0.06869(9) 0.43614(12) 0.0619(4) Uani 1 1 d . . .
C10 C 0.72148(18) 0.12637(11) 0.37156(13) 0.0726(5) Uani 1 1 d . . .
H10 H 0.7502 0.1715 0.3954 0.087 Uiso 1 1 calc R . .
C11 C 0.7029(2) 0.11665(13) 0.27373(14) 0.0823(6) Uani 1 1 d . . .
H11 H 0.7200 0.1547 0.2314 0.099 Uiso 1 1 calc R . .
C12 C 0.65844(19) 0.05002(14) 0.23826(14) 0.0866(6) Uani 1 1 d . . .
H12 H 0.6461 0.0435 0.1719 0.104 Uiso 1 1 calc R . .
C13 C 0.63249(18) -0.00628(12) 0.29964(14) 0.0781(6) Uani 1 1 d . . .
H13 H 0.6015 -0.0503 0.2743 0.094 Uiso 1 1 calc R . .
C14 C 0.65157(15) 0.00078(10) 0.40017(12) 0.0639(5) Uani 1 1 d . . .
C15 C 0.62620(15) -0.05839(9) 0.46760(13) 0.0625(4) Uani 1 1 d . . .
C16 C 0.57737(18) -0.12663(11) 0.43659(15) 0.0766(6) Uani 1 1 d . . .
H16 H 0.5611 -0.1345 0.3709 0.092 Uiso 1 1 calc R . .
C17 C 0.55344(19) -0.18134(11) 0.50049(17) 0.0851(6) Uani 1 1 d . . .
H17 H 0.5210 -0.2259 0.4781 0.102 Uiso 1 1 calc R . .
C18 C 0.57714(19) -0.17093(10) 0.59859(16) 0.0808(6) Uani 1 1 d . . .
H18 H 0.5622 -0.2088 0.6419 0.097 Uiso 1 1 calc R . .
C19 C 0.62243(17) -0.10514(9) 0.63193(14) 0.0701(5) Uani 1 1 d . . .
H19 H 0.6368 -0.0985 0.6981 0.084 Uiso 1 1 calc R . .
C20 C 0.64783(14) -0.04735(9) 0.56832(12) 0.0587(4) Uani 1 1 d . . .
C21 C 0.88461(17) 0.16282(10) 0.56666(12) 0.0653(5) Uani 1 1 d . . .
C22 C 0.95643(19) 0.11608(12) 0.51632(15) 0.0790(6) Uani 1 1 d . . .
H22 H 0.9249 0.0736 0.4871 0.095 Uiso 1 1 calc R . .
C23 C 1.0728(2) 0.13125(15) 0.50871(18) 0.0978(7) Uani 1 1 d U . .
H23 H 1.1191 0.0988 0.4751 0.117 Uiso 1 1 calc R . .
C24 C 1.1215(2) 0.19374(18) 0.5501(2) 0.1071(8) Uani 1 1 d U . .
H24 H 1.2005 0.2040 0.5454 0.129 Uiso 1 1 calc R . .
C25 C 1.0513(3) 0.24099(16) 0.59876(18) 0.1033(8) Uani 1 1 d . . .
H25 H 1.0834 0.2839 0.6265 0.124 Uiso 1 1 calc R . .
C26 C 0.9343(2) 0.22635(12) 0.60743(14) 0.0824(6) Uani 1 1 d . . .
H26 H 0.8886 0.2593 0.6408 0.099 Uiso 1 1 calc R . .
C27 C 0.79687(16) -0.00028(9) 0.76171(12) 0.0597(4) Uani 1 1 d . . .
C28 C 0.90996(17) 0.00072(10) 0.73290(14) 0.0662(5) Uani 1 1 d . . .
H28 H 0.9260 0.0225 0.6741 0.079 Uiso 1 1 calc R . .
C29 C 1.00063(17) -0.03029(10) 0.79023(14) 0.0705(5) Uani 1 1 d . . .
H29 H 1.0763 -0.0296 0.7691 0.085 Uiso 1 1 calc R . .
C30 C 0.97897(17) -0.06212(9) 0.87860(13) 0.0660(5) Uani 1 1 d . . .
C31 C 0.86241(16) -0.06554(8) 0.90808(12) 0.0598(4) Uani 1 1 d . . .
C32 C 0.76985(16) -0.03553(9) 0.84794(12) 0.0598(4) Uani 1 1 d . . .
C33 C 0.65264(17) -0.04425(10) 0.87873(13) 0.0685(5) Uani 1 1 d . . .
H33 H 0.5906 -0.0265 0.8394 0.082 Uiso 1 1 calc R . .
C34 C 0.6307(2) -0.07749(11) 0.96302(14) 0.0756(5) Uani 1 1 d . . .
H34 H 0.5537 -0.0827 0.9798 0.091 Uiso 1 1 calc R . .
C35 C 0.7221(2) -0.10491(10) 1.02735(13) 0.0734(5) Uani 1 1 d U . .
C36 C 0.7014(2) -0.13790(12) 1.11575(15) 0.0921(7) Uani 1 1 d . . .
H36 H 0.6250 -0.1439 1.1338 0.111 Uiso 1 1 calc R . .
C37 C 0.7921(3) -0.16169(13) 1.17675(16) 0.1029(8) Uani 1 1 d . . .
H37 H 0.7767 -0.1822 1.2364 0.123 Uiso 1 1 calc R . .
C38 C 0.9056(3) -0.15544(12) 1.15027(15) 0.0937(7) Uani 1 1 d . . .
H38 H 0.9659 -0.1716 1.1925 0.112 Uiso 1 1 calc R . .
C39 C 0.9320(2) -0.12508(10) 1.06070(13) 0.0757(5) Uani 1 1 d U . .
C40 C 0.83879(18) -0.09874(9) 0.99869(12) 0.0661(4) Uani 1 1 d U . .
C41 C 1.0474(2) -0.11926(11) 1.03003(16) 0.0832(5) Uani 1 1 d U . .
H41 H 1.1089 -0.1359 1.0709 0.100 Uiso 1 1 calc R . .
C42 C 1.07134(19) -0.09026(11) 0.94293(15) 0.0794(6) Uani 1 1 d . . .
H42 H 1.1481 -0.0885 0.9245 0.095 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 C7 1.429(2) . ?
N1 C1 1.434(2) . ?
N1 C27 1.454(2) . ?
N2 C21 1.424(2) . ?
N2 C6 1.427(2) . ?
N2 C8 1.430(2) . ?
C1 C6 1.387(2) . ?
C1 C2 1.390(3) . ?
C2 C3 1.382(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.372(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.371(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.393(2) . ?
C5 H5 0.9300 . ?
C7 C8 1.354(2) . ?
C7 C20 1.446(2) . ?
C8 C9 1.437(2) . ?
C9 C10 1.407(3) . ?
C9 C14 1.412(2) . ?
C10 C11 1.371(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.383(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.365(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.403(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.456(3) . ?
C15 C16 1.408(2) . ?
C15 C20 1.418(2) . ?
C16 C17 1.361(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.384(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.364(3) . ?
C18 H18 0.9300 . ?
C19 C20 1.404(2) . ?
C19 H19 0.9300 . ?
C21 C26 1.385(3) . ?
C21 C22 1.390(3) . ?
C22 C23 1.372(3) . ?
C22 H22 0.9300 . ?
C23 C24 1.368(4) . ?
C23 H23 0.9300 . ?
C24 C25 1.371(4) . ?
C24 H24 0.9300 . ?
C25 C26 1.379(3) . ?
C25 H25 0.9300 . ?
C26 H26 0.9300 . ?
C27 C28 1.377(3) . ?
C27 C32 1.401(2) . ?
C28 C29 1.392(3) . ?
C28 H28 0.9300 . ?
C29 C30 1.385(3) . ?
C29 H29 0.9300 . ?
C30 C31 1.419(3) . ?
C30 C42 1.440(3) . ?
C31 C32 1.421(2) . ?
C31 C40 1.428(2) . ?
C32 C33 1.440(3) . ?
C33 C34 1.347(3) . ?
C33 H33 0.9300 . ?
C34 C35 1.428(3) . ?
C34 H34 0.9300 . ?
C35 C36 1.392(3) . ?
C35 C40 1.420(3) . ?
C36 C37 1.374(3) . ?
C36 H36 0.9300 . ?
C37 C38 1.374(4) . ?
C37 H37 0.9300 . ?
C38 C39 1.403(3) . ?
C38 H38 0.9300 . ?
C39 C41 1.415(3) . ?
C39 C40 1.417(3) . ?
C41 C42 1.355(3) . ?
C41 H41 0.9300 . ?
C42 H42 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
C7 N1 C1 113.70(13) . . ?
C7 N1 C27 118.36(13) . . ?
C1 N1 C27 116.27(12) . . ?
C21 N2 C6 119.19(14) . . ?
C21 N2 C8 118.41(14) . . ?
C6 N2 C8 111.92(14) . . ?
C6 C1 C2 118.55(16) . . ?
C6 C1 N1 118.96(15) . . ?
C2 C1 N1 122.42(16) . . ?
C3 C2 C1 120.18(19) . . ?
C3 C2 H2 119.9 . . ?
C1 C2 H2 119.9 . . ?
C4 C3 C2 120.7(2) . . ?
C4 C3 H3 119.6 . . ?
C2 C3 H3 119.6 . . ?
C5 C4 C3 119.94(18) . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
C4 C5 C6 119.77(19) . . ?
C4 C5 H5 120.1 . . ?
C6 C5 H5 120.1 . . ?
C1 C6 C5 120.62(17) . . ?
C1 C6 N2 117.77(14) . . ?
C5 C6 N2 121.59(17) . . ?
C8 C7 N1 119.58(14) . . ?
C8 C7 C20 120.58(15) . . ?
N1 C7 C20 119.51(15) . . ?
C7 C8 N2 118.76(14) . . ?
C7 C8 C9 122.15(15) . . ?
N2 C8 C9 119.00(15) . . ?
C10 C9 C14 119.79(16) . . ?
C10 C9 C8 121.22(16) . . ?
C14 C9 C8 118.99(16) . . ?
C11 C10 C9 120.54(19) . . ?
C11 C10 H10 119.7 . . ?
C9 C10 H10 119.7 . . ?
C10 C11 C12 119.8(2) . . ?
C10 C11 H11 120.1 . . ?
C12 C11 H11 120.1 . . ?
C13 C12 C11 120.74(18) . . ?
C13 C12 H12 119.6 . . ?
C11 C12 H12 119.6 . . ?
C12 C13 C14 121.5(2) . . ?
C12 C13 H13 119.3 . . ?
C14 C13 H13 119.3 . . ?
C13 C14 C9 117.67(18) . . ?
C13 C14 C15 122.93(17) . . ?
C9 C14 C15 119.40(15) . . ?
C16 C15 C20 117.96(18) . . ?
C16 C15 C14 122.19(17) . . ?
C20 C15 C14 119.83(15) . . ?
C17 C16 C15 121.57(18) . . ?
C17 C16 H16 119.2 . . ?
C15 C16 H16 119.2 . . ?
C16 C17 C18 120.26(18) . . ?
C16 C17 H17 119.9 . . ?
C18 C17 H17 119.9 . . ?
C19 C18 C17 120.1(2) . . ?
C19 C18 H18 120.0 . . ?
C17 C18 H18 120.0 . . ?
C18 C19 C20 121.28(18) . . ?
C18 C19 H19 119.4 . . ?
C20 C19 H19 119.4 . . ?
C19 C20 C15 118.80(15) . . ?
C19 C20 C7 122.17(15) . . ?
C15 C20 C7 119.02(16) . . ?
C26 C21 C22 117.5(2) . . ?
C26 C21 N2 121.14(19) . . ?
C22 C21 N2 121.33(17) . . ?
C23 C22 C21 121.5(2) . . ?
C23 C22 H22 119.3 . . ?
C21 C22 H22 119.3 . . ?
C24 C23 C22 120.6(3) . . ?
C24 C23 H23 119.7 . . ?
C22 C23 H23 119.7 . . ?
C23 C24 C25 118.6(3) . . ?
C23 C24 H24 120.7 . . ?
C25 C24 H24 120.7 . . ?
C24 C25 C26 121.5(2) . . ?
C24 C25 H25 119.2 . . ?
C26 C25 H25 119.2 . . ?
C25 C26 C21 120.3(2) . . ?
C25 C26 H26 119.9 . . ?
C21 C26 H26 119.9 . . ?
C28 C27 C32 120.43(16) . . ?
C28 C27 N1 119.49(16) . . ?
C32 C27 N1 120.05(16) . . ?
C27 C28 C29 121.11(18) . . ?
C27 C28 H28 119.4 . . ?
C29 C28 H28 119.4 . . ?
C30 C29 C28 120.44(19) . . ?
C30 C29 H29 119.8 . . ?
C28 C29 H29 119.8 . . ?
C29 C30 C31 119.14(16) . . ?
C29 C30 C42 122.13(19) . . ?
C31 C30 C42 118.71(18) . . ?
C30 C31 C32 120.06(16) . . ?
C30 C31 C40 119.70(16) . . ?
C32 C31 C40 120.24(18) . . ?
C27 C32 C31 118.67(17) . . ?
C27 C32 C33 123.58(16) . . ?
C31 C32 C33 117.74(16) . . ?
C34 C33 C32 121.64(18) . . ?
C34 C33 H33 119.2 . . ?
C32 C33 H33 119.2 . . ?
C33 C34 C35 122.0(2) . . ?
C33 C34 H34 119.0 . . ?
C35 C34 H34 119.0 . . ?
C36 C35 C40 119.1(2) . . ?
C36 C35 C34 122.8(2) . . ?
C40 C35 C34 118.09(18) . . ?
C37 C36 C35 121.0(3) . . ?
C37 C36 H36 119.5 . . ?
C35 C36 H36 119.5 . . ?
C36 C37 C38 120.5(2) . . ?
C36 C37 H37 119.7 . . ?
C38 C37 H37 119.7 . . ?
C37 C38 C39 121.3(2) . . ?
C37 C38 H38 119.4 . . ?
C39 C38 H38 119.4 . . ?
C38 C39 C41 122.9(2) . . ?
C38 C39 C40 118.3(2) . . ?
C41 C39 C40 118.77(19) . . ?
C39 C40 C35 119.78(18) . . ?
C39 C40 C31 120.03(19) . . ?
C35 C40 C31 120.19(17) . . ?
C42 C41 C39 122.10(19) . . ?
C42 C41 H41 119.0 . . ?
C39 C41 H41 119.0 . . ?
C41 C42 C30 120.6(2) . . ?
C41 C42 H42 119.7 . . ?
C30 C42 H42 119.7 . . ?

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
C7 N1 C1 C6 -27.6(2) . . . . ?
C27 N1 C1 C6 115.10(18) . . . . ?
C7 N1 C1 C2 149.21(17) . . . . ?
C27 N1 C1 C2 -68.1(2) . . . . ?
C6 C1 C2 C3 2.2(3) . . . . ?
N1 C1 C2 C3 -174.57(18) . . . . ?
C1 C2 C3 C4 1.5(3) . . . . ?
C2 C3 C4 C5 -2.1(4) . . . . ?
C3 C4 C5 C6 -1.0(3) . . . . ?
C2 C1 C6 C5 -5.3(3) . . . . ?
N1 C1 C6 C5 171.57(16) . . . . ?
C2 C1 C6 N2 176.22(16) . . . . ?
N1 C1 C6 N2 -6.9(2) . . . . ?
C4 C5 C6 C1 4.8(3) . . . . ?
C4 C5 C6 N2 -176.83(18) . . . . ?
C21 N2 C6 C1 -104.67(18) . . . . ?
C8 N2 C6 C1 39.7(2) . . . . ?
C21 N2 C6 C5 76.9(2) . . . . ?
C8 N2 C6 C5 -138.77(17) . . . . ?
C1 N1 C7 C8 28.9(2) . . . . ?
C27 N1 C7 C8 -112.93(18) . . . . ?
C1 N1 C7 C20 -144.53(15) . . . . ?
C27 N1 C7 C20 73.6(2) . . . . ?
N1 C7 C8 N2 4.6(2) . . . . ?
C20 C7 C8 N2 178.00(14) . . . . ?
N1 C7 C8 C9 -171.86(15) . . . . ?
C20 C7 C8 C9 1.5(3) . . . . ?
C21 N2 C8 C7 105.73(18) . . . . ?
C6 N2 C8 C7 -38.9(2) . . . . ?
C21 N2 C8 C9 -77.66(19) . . . . ?
C6 N2 C8 C9 137.72(16) . . . . ?
C7 C8 C9 C10 178.76(17) . . . . ?
N2 C8 C9 C10 2.3(3) . . . . ?
C7 C8 C9 C14 -2.0(3) . . . . ?
N2 C8 C9 C14 -178.50(15) . . . . ?
C14 C9 C10 C11 -1.4(3) . . . . ?
C8 C9 C10 C11 177.87(18) . . . . ?
C9 C10 C11 C12 1.0(3) . . . . ?
C10 C11 C12 C13 0.2(3) . . . . ?
C11 C12 C13 C14 -1.1(3) . . . . ?
C12 C13 C14 C9 0.7(3) . . . . ?
C12 C13 C14 C15 -179.26(18) . . . . ?
C10 C9 C14 C13 0.5(3) . . . . ?
C8 C9 C14 C13 -178.75(16) . . . . ?
C10 C9 C14 C15 -179.52(16) . . . . ?
C8 C9 C14 C15 1.2(2) . . . . ?
C13 C14 C15 C16 -1.8(3) . . . . ?
C9 C14 C15 C16 178.24(16) . . . . ?
C13 C14 C15 C20 179.93(17) . . . . ?
C9 C14 C15 C20 0.0(2) . . . . ?
C20 C15 C16 C17 -1.3(3) . . . . ?
C14 C15 C16 C17 -179.60(18) . . . . ?
C15 C16 C17 C18 -0.1(3) . . . . ?
C16 C17 C18 C19 1.3(3) . . . . ?
C17 C18 C19 C20 -1.1(3) . . . . ?
C18 C19 C20 C15 -0.3(3) . . . . ?
C18 C19 C20 C7 -179.99(17) . . . . ?
C16 C15 C20 C19 1.5(2) . . . . ?
C14 C15 C20 C19 179.86(16) . . . . ?
C16 C15 C20 C7 -178.83(15) . . . . ?
C14 C15 C20 C7 -0.5(2) . . . . ?
C8 C7 C20 C19 179.41(16) . . . . ?
N1 C7 C20 C19 -7.2(2) . . . . ?
C8 C7 C20 C15 -0.2(2) . . . . ?
N1 C7 C20 C15 173.13(14) . . . . ?
C6 N2 C21 C26 -32.8(2) . . . . ?
C8 N2 C21 C26 -174.88(15) . . . . ?
C6 N2 C21 C22 147.81(16) . . . . ?
C8 N2 C21 C22 5.8(2) . . . . ?
C26 C21 C22 C23 1.3(3) . . . . ?
N2 C21 C22 C23 -179.33(17) . . . . ?
C21 C22 C23 C24 -0.6(3) . . . . ?
C22 C23 C24 C25 -0.4(3) . . . . ?
C23 C24 C25 C26 0.7(4) . . . . ?
C24 C25 C26 C21 0.0(3) . . . . ?
C22 C21 C26 C25 -1.0(3) . . . . ?
N2 C21 C26 C25 179.64(17) . . . . ?
C7 N1 C27 C28 50.6(2) . . . . ?
C1 N1 C27 C28 -90.30(19) . . . . ?
C7 N1 C27 C32 -131.46(16) . . . . ?
C1 N1 C27 C32 87.67(19) . . . . ?
C32 C27 C28 C29 -2.7(3) . . . . ?
N1 C27 C28 C29 175.23(15) . . . . ?
C27 C28 C29 C30 -0.9(3) . . . . ?
C28 C29 C30 C31 2.7(3) . . . . ?
C28 C29 C30 C42 -175.71(16) . . . . ?
C29 C30 C31 C32 -1.0(2) . . . . ?
C42 C30 C31 C32 177.47(15) . . . . ?
C29 C30 C31 C40 179.51(15) . . . . ?
C42 C30 C31 C40 -2.1(2) . . . . ?
C28 C27 C32 C31 4.3(2) . . . . ?
N1 C27 C32 C31 -173.61(13) . . . . ?
C28 C27 C32 C33 -174.65(16) . . . . ?
N1 C27 C32 C33 7.4(2) . . . . ?
C30 C31 C32 C27 -2.5(2) . . . . ?
C40 C31 C32 C27 177.03(14) . . . . ?
C30 C31 C32 C33 176.54(15) . . . . ?
C40 C31 C32 C33 -3.9(2) . . . . ?
C27 C32 C33 C34 -178.92(17) . . . . ?
C31 C32 C33 C34 2.1(2) . . . . ?
C32 C33 C34 C35 1.0(3) . . . . ?
C33 C34 C35 C36 178.50(19) . . . . ?
C33 C34 C35 C40 -2.2(3) . . . . ?
C40 C35 C36 C37 2.6(3) . . . . ?
C34 C35 C36 C37 -178.17(19) . . . . ?
C35 C36 C37 C38 -2.0(3) . . . . ?
C36 C37 C38 C39 -0.2(3) . . . . ?
C37 C38 C39 C41 -178.6(2) . . . . ?
C37 C38 C39 C40 1.8(3) . . . . ?
C38 C39 C40 C35 -1.2(2) . . . . ?
C41 C39 C40 C35 179.15(16) . . . . ?
C38 C39 C40 C31 178.23(16) . . . . ?
C41 C39 C40 C31 -1.4(2) . . . . ?
C36 C35 C40 C39 -0.9(3) . . . . ?
C34 C35 C40 C39 179.78(16) . . . . ?
C36 C35 C40 C31 179.62(16) . . . . ?
C34 C35 C40 C31 0.3(2) . . . . ?
C30 C31 C40 C39 2.8(2) . . . . ?
C32 C31 C40 C39 -176.69(14) . . . . ?
C30 C31 C40 C35 -177.70(15) . . . . ?
C32 C31 C40 C35 2.8(2) . . . . ?
C38 C39 C41 C42 179.52(18) . . . . ?
C40 C39 C41 C42 -0.9(3) . . . . ?
C39 C41 C42 C30 1.7(3) . . . . ?
C29 C30 C42 C41 178.22(17) . . . . ?
C31 C30 C42 C41 -0.2(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.163
_refine_diff_density_min         -0.122
_refine_diff_density_rms         0.029


####################################################################### 
# 
# 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_cd15118
_database_code_depnum_ccdc_archive 'CCDC 1422600'
_audit_update_record             
;
2015-09-07 deposited with the CCDC.
2016-03-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C33 H24 N2'
_chemical_formula_weight         448.54

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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

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

_cell_length_a                   13.670(2)
_cell_length_b                   10.7087(18)
_cell_length_c                   16.477(3)
_cell_angle_alpha                90
_cell_angle_beta                 98.766(4)
_cell_angle_gamma                90
_cell_volume                     2384.0(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1613
_cell_measurement_theta_min      4.552
_cell_measurement_theta_max      43.547

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.250
_exptl_crystal_F_000             944
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.130
_exptl_absorpt_coefficient_mu    0.073
_shelx_estimated_absorpt_T_min   0.984
_shelx_estimated_absorpt_T_max   0.991
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6237
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13421
_diffrn_reflns_av_unetI/netI     0.0524
_diffrn_reflns_av_R_equivalents  0.0480
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.806
_diffrn_reflns_theta_max         25.500
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4424
_reflns_number_gt                2949
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 ? 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0551P)²+0.5024P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4424
_refine_ls_number_parameters     317
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1028
_refine_ls_R_factor_gt           0.0653
_refine_ls_wR_factor_ref         0.1521
_refine_ls_wR_factor_gt          0.1363
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_restrained_S_all      1.095
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 1.04754(14) 0.13179(18) 0.22783(12) 0.0441(5) Uani 1 1 d . . . . .
N2 N 1.03107(14) -0.10046(18) 0.29292(11) 0.0452(5) Uani 1 1 d . . . . .
C1 C 0.93818(17) 0.0733(2) 0.09943(14) 0.0451(6) Uani 1 1 d . . . . .
C2 C 0.94623(19) 0.1930(3) 0.06707(16) 0.0573(7) Uani 1 1 d . . . . .
H2 H 0.9821 0.2540 0.0990 0.069 Uiso 1 1 calc R U . . .
C3 C 0.9026(2) 0.2214(3) -0.01022(17) 0.0689(8) Uani 1 1 d . . . . .
H3 H 0.9085 0.3014 -0.0309 0.083 Uiso 1 1 calc R U . . .
C4 C 0.8493(2) 0.1313(3) -0.05824(17) 0.0706(9) Uani 1 1 d . . . . .
H4 H 0.8193 0.1512 -0.1112 0.085 Uiso 1 1 calc R U . . .
C5 C 0.8403(2) 0.0132(3) -0.02856(16) 0.0625(8) Uani 1 1 d . . . . .
H5 H 0.8045 -0.0462 -0.0618 0.075 Uiso 1 1 calc R U . . .
C6 C 0.88437(17) -0.0200(3) 0.05152(14) 0.0487(6) Uani 1 1 d . . . . .
C7 C 0.87851(17) -0.1452(3) 0.08410(14) 0.0486(6) Uani 1 1 d . . . . .
C8 C 0.8279(2) -0.2430(3) 0.03980(17) 0.0695(9) Uani 1 1 d . . . . .
H8 H 0.7945 -0.2271 -0.0127 0.083 Uiso 1 1 calc R U . . .
C9 C 0.8259(2) -0.3602(3) 0.07053(19) 0.0782(10) Uani 1 1 d . . . . .
H9 H 0.7907 -0.4225 0.0394 0.094 Uiso 1 1 calc R U . . .
C10 C 0.8762(2) -0.3880(3) 0.14832(18) 0.0689(9) Uani 1 1 d . . . . .
H10 H 0.8760 -0.4689 0.1687 0.083 Uiso 1 1 calc R U . . .
C11 C 0.92559(18) -0.2954(2) 0.19445(16) 0.0519(7) Uani 1 1 d . . . . .
H11 H 0.9586 -0.3138 0.2467 0.062 Uiso 1 1 calc R U . . .
C12 C 0.92746(16) -0.1733(2) 0.16462(14) 0.0439(6) Uani 1 1 d . . . . .
C13 C 0.97787(16) -0.0739(2) 0.21268(13) 0.0423(6) Uani 1 1 d . . . . .
C14 C 0.98502(16) 0.0417(2) 0.18127(13) 0.0416(6) Uani 1 1 d . . . . .
C15 C 1.00222(17) 0.2309(2) 0.26750(13) 0.0412(6) Uani 1 1 d . . . . .
C16 C 0.90217(18) 0.2299(2) 0.27147(15) 0.0522(7) Uani 1 1 d . . . . .
H16 H 0.8631 0.1648 0.2472 0.063 Uiso 1 1 calc R U . . .
C17 C 0.8596(2) 0.3241(3) 0.31094(17) 0.0597(7) Uani 1 1 d . . . . .
H17 H 0.7920 0.3211 0.3131 0.072 Uiso 1 1 calc R U . . .
C18 C 0.9144(2) 0.4228(3) 0.34731(17) 0.0605(7) Uani 1 1 d . . . . .
C19 C 1.0138(2) 0.4229(3) 0.34253(17) 0.0626(8) Uani 1 1 d . . . . .
H19 H 1.0528 0.4881 0.3666 0.075 Uiso 1 1 calc R U . . .
C20 C 1.05746(19) 0.3297(2) 0.30337(16) 0.0540(7) Uani 1 1 d . . . . .
H20 H 1.1249 0.3332 0.3010 0.065 Uiso 1 1 calc R U . . .
C21 C 0.8688(3) 0.5253(3) 0.3921(2) 0.1012(12) Uani 1 1 d . . . . .
H21A H 0.8588 0.4957 0.4453 0.152 Uiso 1 1 calc R U . . .
H21B H 0.8063 0.5491 0.3612 0.152 Uiso 1 1 calc R U . . .
H21C H 0.9122 0.5962 0.3985 0.152 Uiso 1 1 calc R U . . .
C22 C 1.13545(17) 0.0740(2) 0.27082(14) 0.0434(6) Uani 1 1 d . . . . .
C23 C 1.22796(18) 0.1291(3) 0.27481(16) 0.0543(7) Uani 1 1 d . . . . .
H23 H 1.2343 0.2063 0.2504 0.065 Uiso 1 1 calc R U . . .
C24 C 1.31061(19) 0.0686(3) 0.31529(17) 0.0613(8) Uani 1 1 d . . . . .
H24 H 1.3725 0.1060 0.3189 0.074 Uiso 1 1 calc R U . . .
C25 C 1.3017(2) -0.0466(3) 0.35014(17) 0.0625(8) Uani 1 1 d . . . . .
H25 H 1.3574 -0.0862 0.3781 0.075 Uiso 1 1 calc R U . . .
C26 C 1.21044(19) -0.1038(3) 0.34388(15) 0.0523(7) Uani 1 1 d . . . . .
H26 H 1.2051 -0.1832 0.3656 0.063 Uiso 1 1 calc R U . . .
C27 C 1.12665(17) -0.0429(2) 0.30519(13) 0.0423(6) Uani 1 1 d . . . . .
C28 C 0.97741(18) -0.1207(2) 0.35929(14) 0.0420(6) Uani 1 1 d . . . . .
C29 C 1.0253(2) -0.1447(3) 0.43814(15) 0.0571(7) Uani 1 1 d . . . . .
H29 H 1.0941 -0.1457 0.4486 0.069 Uiso 1 1 calc R U . . .
C30 C 0.9718(2) -0.1672(3) 0.50101(17) 0.0680(8) Uani 1 1 d . . . . .
H30 H 1.0051 -0.1818 0.5537 0.082 Uiso 1 1 calc R U . . .
C31 C 0.8702(2) -0.1684(3) 0.48716(18) 0.0661(8) Uani 1 1 d . . . . .
H31 H 0.8345 -0.1857 0.5296 0.079 Uiso 1 1 calc R U . . .
C32 C 0.8225(2) -0.1436(3) 0.40971(17) 0.0610(7) Uani 1 1 d . . . . .
H32 H 0.7537 -0.1438 0.3996 0.073 Uiso 1 1 calc R U . . .
C33 C 0.87487(19) -0.1184(2) 0.34648(16) 0.0533(7) Uani 1 1 d . . . . .
H33 H 0.8410 -0.0995 0.2946 0.064 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C14 1.431(3) . ?
N1 C15 1.436(3) . ?
N1 C22 1.438(3) . ?
N2 C28 1.423(3) . ?
N2 C27 1.431(3) . ?
N2 C13 1.437(3) . ?
C1 C2 1.399(3) . ?
C1 C6 1.409(3) . ?
C1 C14 1.442(3) . ?
C2 C3 1.356(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.383(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.368(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.410(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.450(4) . ?
C7 C8 1.398(4) . ?
C7 C12 1.424(3) . ?
C8 C9 1.355(4) . ?
C8 H8 0.9300 . ?
C9 C10 1.391(4) . ?
C9 H9 0.9300 . ?
C10 C11 1.364(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.398(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.438(3) . ?
C13 C14 1.352(3) . ?
C15 C16 1.379(3) . ?
C15 C20 1.379(3) . ?
C16 C17 1.377(4) . ?
C16 H16 0.9300 . ?
C17 C18 1.379(4) . ?
C17 H17 0.9300 . ?
C18 C19 1.373(4) . ?
C18 C21 1.510(4) . ?
C19 C20 1.373(4) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 C27 1.387(3) . ?
C22 C23 1.388(3) . ?
C23 C24 1.383(4) . ?
C23 H23 0.9300 . ?
C24 C25 1.374(4) . ?
C24 H24 0.9300 . ?
C25 C26 1.379(4) . ?
C25 H25 0.9300 . ?
C26 C27 1.386(3) . ?
C26 H26 0.9300 . ?
C28 C33 1.386(3) . ?
C28 C29 1.387(3) . ?
C29 C30 1.377(4) . ?
C29 H29 0.9300 . ?
C30 C31 1.373(4) . ?
C30 H30 0.9300 . ?
C31 C32 1.368(4) . ?
C31 H31 0.9300 . ?
C32 C33 1.378(4) . ?
C32 H32 0.9300 . ?
C33 H33 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
C14 N1 C15 118.57(18) . . ?
C14 N1 C22 111.09(19) . . ?
C15 N1 C22 118.68(18) . . ?
C28 N2 C27 121.56(18) . . ?
C28 N2 C13 119.29(18) . . ?
C27 N2 C13 111.59(19) . . ?
C2 C1 C6 120.1(2) . . ?
C2 C1 C14 121.4(2) . . ?
C6 C1 C14 118.5(2) . . ?
C3 C2 C1 121.0(3) . . ?
C3 C2 H2 119.5 . . ?
C1 C2 H2 119.5 . . ?
C2 C3 C4 119.9(3) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C5 C4 C3 120.6(3) . . ?
C5 C4 H4 119.7 . . ?
C3 C4 H4 119.7 . . ?
C4 C5 C6 121.3(3) . . ?
C4 C5 H5 119.4 . . ?
C6 C5 H5 119.4 . . ?
C1 C6 C5 117.2(3) . . ?
C1 C6 C7 120.1(2) . . ?
C5 C6 C7 122.7(2) . . ?
C8 C7 C12 116.9(3) . . ?
C8 C7 C6 123.4(2) . . ?
C12 C7 C6 119.7(2) . . ?
C9 C8 C7 122.4(3) . . ?
C9 C8 H8 118.8 . . ?
C7 C8 H8 118.8 . . ?
C8 C9 C10 120.5(3) . . ?
C8 C9 H9 119.8 . . ?
C10 C9 H9 119.8 . . ?
C11 C10 C9 119.4(3) . . ?
C11 C10 H10 120.3 . . ?
C9 C10 H10 120.3 . . ?
C10 C11 C12 121.2(2) . . ?
C10 C11 H11 119.4 . . ?
C12 C11 H11 119.4 . . ?
C11 C12 C7 119.6(2) . . ?
C11 C12 C13 122.1(2) . . ?
C7 C12 C13 118.3(2) . . ?
C14 C13 N2 118.5(2) . . ?
C14 C13 C12 121.6(2) . . ?
N2 C13 C12 119.5(2) . . ?
C13 C14 N1 118.96(19) . . ?
C13 C14 C1 121.7(2) . . ?
N1 C14 C1 119.2(2) . . ?
C16 C15 C20 117.9(2) . . ?
C16 C15 N1 121.0(2) . . ?
C20 C15 N1 121.1(2) . . ?
C17 C16 C15 120.7(2) . . ?
C17 C16 H16 119.7 . . ?
C15 C16 H16 119.7 . . ?
C16 C17 C18 121.7(3) . . ?
C16 C17 H17 119.1 . . ?
C18 C17 H17 119.1 . . ?
C19 C18 C17 116.9(3) . . ?
C19 C18 C21 120.9(3) . . ?
C17 C18 C21 122.1(3) . . ?
C18 C19 C20 122.1(3) . . ?
C18 C19 H19 119.0 . . ?
C20 C19 H19 119.0 . . ?
C19 C20 C15 120.7(3) . . ?
C19 C20 H20 119.7 . . ?
C15 C20 H20 119.7 . . ?
C18 C21 H21A 109.5 . . ?
C18 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C18 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C27 C22 C23 120.0(2) . . ?
C27 C22 N1 118.1(2) . . ?
C23 C22 N1 121.8(2) . . ?
C24 C23 C22 119.7(3) . . ?
C24 C23 H23 120.1 . . ?
C22 C23 H23 120.1 . . ?
C25 C24 C23 120.3(3) . . ?
C25 C24 H24 119.9 . . ?
C23 C24 H24 119.9 . . ?
C24 C25 C26 120.3(2) . . ?
C24 C25 H25 119.8 . . ?
C26 C25 H25 119.8 . . ?
C25 C26 C27 120.0(3) . . ?
C25 C26 H26 120.0 . . ?
C27 C26 H26 120.0 . . ?
C26 C27 C22 119.7(2) . . ?
C26 C27 N2 122.3(2) . . ?
C22 C27 N2 117.74(19) . . ?
C33 C28 C29 117.9(2) . . ?
C33 C28 N2 120.5(2) . . ?
C29 C28 N2 121.5(2) . . ?
C30 C29 C28 120.5(3) . . ?
C30 C29 H29 119.7 . . ?
C28 C29 H29 119.7 . . ?
C31 C30 C29 121.1(3) . . ?
C31 C30 H30 119.5 . . ?
C29 C30 H30 119.5 . . ?
C32 C31 C30 118.7(3) . . ?
C32 C31 H31 120.7 . . ?
C30 C31 H31 120.7 . . ?
C31 C32 C33 121.0(3) . . ?
C31 C32 H32 119.5 . . ?
C33 C32 H32 119.5 . . ?
C32 C33 C28 120.8(2) . . ?
C32 C33 H33 119.6 . . ?
C28 C33 H33 119.6 . . ?

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
C6 C1 C2 C3 0.2(4) . . . . ?
C14 C1 C2 C3 179.5(2) . . . . ?
C1 C2 C3 C4 -0.1(4) . . . . ?
C2 C3 C4 C5 -0.2(5) . . . . ?
C3 C4 C5 C6 0.3(4) . . . . ?
C2 C1 C6 C5 0.0(4) . . . . ?
C14 C1 C6 C5 -179.3(2) . . . . ?
C2 C1 C6 C7 178.1(2) . . . . ?
C14 C1 C6 C7 -1.2(3) . . . . ?
C4 C5 C6 C1 -0.2(4) . . . . ?
C4 C5 C6 C7 -178.3(3) . . . . ?
C1 C6 C7 C8 -178.9(3) . . . . ?
C5 C6 C7 C8 -0.9(4) . . . . ?
C1 C6 C7 C12 -0.1(4) . . . . ?
C5 C6 C7 C12 178.0(2) . . . . ?
C12 C7 C8 C9 -0.9(4) . . . . ?
C6 C7 C8 C9 177.9(3) . . . . ?
C7 C8 C9 C10 -0.8(5) . . . . ?
C8 C9 C10 C11 1.6(5) . . . . ?
C9 C10 C11 C12 -0.6(4) . . . . ?
C10 C11 C12 C7 -1.2(4) . . . . ?
C10 C11 C12 C13 179.1(3) . . . . ?
C8 C7 C12 C11 1.9(4) . . . . ?
C6 C7 C12 C11 -177.0(2) . . . . ?
C8 C7 C12 C13 -178.3(2) . . . . ?
C6 C7 C12 C13 2.8(3) . . . . ?
C28 N2 C13 C14 111.1(2) . . . . ?
C27 N2 C13 C14 -39.1(3) . . . . ?
C28 N2 C13 C12 -75.5(3) . . . . ?
C27 N2 C13 C12 134.4(2) . . . . ?
C11 C12 C13 C14 175.4(2) . . . . ?
C7 C12 C13 C14 -4.4(4) . . . . ?
C11 C12 C13 N2 2.1(4) . . . . ?
C7 C12 C13 N2 -177.7(2) . . . . ?
N2 C13 C14 N1 2.0(3) . . . . ?
C12 C13 C14 N1 -171.4(2) . . . . ?
N2 C13 C14 C1 176.6(2) . . . . ?
C12 C13 C14 C1 3.3(4) . . . . ?
C15 N1 C14 C13 -105.9(2) . . . . ?
C22 N1 C14 C13 36.9(3) . . . . ?
C15 N1 C14 C1 79.4(3) . . . . ?
C22 N1 C14 C1 -137.9(2) . . . . ?
C2 C1 C14 C13 -179.7(2) . . . . ?
C6 C1 C14 C13 -0.4(4) . . . . ?
C2 C1 C14 N1 -5.1(3) . . . . ?
C6 C1 C14 N1 174.2(2) . . . . ?
C14 N1 C15 C16 9.6(3) . . . . ?
C22 N1 C15 C16 -130.3(2) . . . . ?
C14 N1 C15 C20 -170.8(2) . . . . ?
C22 N1 C15 C20 49.3(3) . . . . ?
C20 C15 C16 C17 -0.7(4) . . . . ?
N1 C15 C16 C17 178.8(2) . . . . ?
C15 C16 C17 C18 0.4(4) . . . . ?
C16 C17 C18 C19 -0.1(4) . . . . ?
C16 C17 C18 C21 -178.8(3) . . . . ?
C17 C18 C19 C20 0.1(4) . . . . ?
C21 C18 C19 C20 178.9(3) . . . . ?
C18 C19 C20 C15 -0.5(4) . . . . ?
C16 C15 C20 C19 0.8(4) . . . . ?
N1 C15 C20 C19 -178.8(2) . . . . ?
C14 N1 C22 C27 -38.9(3) . . . . ?
C15 N1 C22 C27 103.8(2) . . . . ?
C14 N1 C22 C23 137.8(2) . . . . ?
C15 N1 C22 C23 -79.5(3) . . . . ?
C27 C22 C23 C24 -1.9(4) . . . . ?
N1 C22 C23 C24 -178.5(2) . . . . ?
C22 C23 C24 C25 1.2(4) . . . . ?
C23 C24 C25 C26 1.1(4) . . . . ?
C24 C25 C26 C27 -2.6(4) . . . . ?
C25 C26 C27 C22 1.9(4) . . . . ?
C25 C26 C27 N2 176.5(2) . . . . ?
C23 C22 C27 C26 0.4(3) . . . . ?
N1 C22 C27 C26 177.1(2) . . . . ?
C23 C22 C27 N2 -174.4(2) . . . . ?
N1 C22 C27 N2 2.3(3) . . . . ?
C28 N2 C27 C26 72.3(3) . . . . ?
C13 N2 C27 C26 -138.3(2) . . . . ?
C28 N2 C27 C22 -113.0(2) . . . . ?
C13 N2 C27 C22 36.4(3) . . . . ?
C27 N2 C28 C33 148.9(2) . . . . ?
C13 N2 C28 C33 1.8(3) . . . . ?
C27 N2 C28 C29 -31.9(3) . . . . ?
C13 N2 C28 C29 -179.0(2) . . . . ?
C33 C28 C29 C30 0.9(4) . . . . ?
N2 C28 C29 C30 -178.3(2) . . . . ?
C28 C29 C30 C31 1.1(4) . . . . ?
C29 C30 C31 C32 -1.6(4) . . . . ?
C30 C31 C32 C33 0.2(4) . . . . ?
C31 C32 C33 C28 1.7(4) . . . . ?
C29 C28 C33 C32 -2.2(4) . . . . ?
N2 C28 C33 C32 176.9(2) . . . . ?

_refine_diff_density_max         0.264
_refine_diff_density_min         -0.160
_refine_diff_density_rms         0.036

_shelxl_version_number           2013-4

