# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_1c060m
_audit_block_doi                 10.5517/ccdc.csd.cc28zrgh
_database_code_depnum_ccdc_archive 'CCDC 2114927'
loop_
_audit_author_name
_audit_author_address
'Lei Zhao'
;chang chun institute of applied chemistry
China
;
_audit_update_record             
;
2021-10-11 deposited with the CCDC.	2022-01-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 2',7'-bis(9,9-dimethylacridin-10(9H)-yl)-10H-spiro[anthracene-9,9'-fluoren]-10-one 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C56 H42 N2 O'
_chemical_formula_sum            'C56 H42 N2 O'
_chemical_formula_weight         758.92

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

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

_cell_length_a                   10.2046(15)
_cell_length_b                   12.2649(19)
_cell_length_c                   18.468(3)
_cell_angle_alpha                70.616(3)
_cell_angle_beta                 88.890(4)
_cell_angle_gamma                68.710(3)
_cell_volume                     2018.1(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    642
_cell_measurement_theta_min      2.3347
_cell_measurement_theta_max      18.9287

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.24
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.249
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             800
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9783
_exptl_absorpt_correction_T_max  0.9826
_exptl_absorpt_process_details   'SADABS; Bruker, 2000'

_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  'Bruker APEX CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10919
_diffrn_reflns_av_R_equivalents  0.0551
_diffrn_reflns_av_sigmaI/netI    0.1779
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.85
_diffrn_reflns_theta_max         26.39
_reflns_number_total             7995
_reflns_number_gt                3322
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART (Bruker, 2007)'
_computing_cell_refinement       'SMART (Bruker, 2007)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  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)+(0.0481P)²+0.0000P] 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         7995
_refine_ls_number_parameters     536
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2124
_refine_ls_R_factor_gt           0.0906
_refine_ls_wR_factor_ref         0.1865
_refine_ls_wR_factor_gt          0.1398
_refine_ls_goodness_of_fit_ref   0.979
_refine_ls_restrained_S_all      0.979
_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
C1 C 1.2904(6) 0.3839(5) 0.7180(3) 0.0816(19) Uani 1 1 d . . .
H1A H 1.3071 0.4140 0.7574 0.122 Uiso 1 1 calc R . .
H1B H 1.3695 0.3093 0.7212 0.122 Uiso 1 1 calc R . .
H1C H 1.2061 0.3659 0.7253 0.122 Uiso 1 1 calc R . .
C2 C 1.4075(5) 0.5166(5) 0.6308(3) 0.0683(17) Uani 1 1 d . . .
H2A H 1.4009 0.5762 0.5804 0.102 Uiso 1 1 calc R . .
H2B H 1.4897 0.4421 0.6382 0.102 Uiso 1 1 calc R . .
H2C H 1.4152 0.5513 0.6693 0.102 Uiso 1 1 calc R . .
C3 C 0.6271(7) 1.6071(5) -0.2204(3) 0.100(2) Uani 1 1 d . . .
H3A H 0.6571 1.5767 -0.2620 0.150 Uiso 1 1 calc R . .
H3B H 0.6346 1.6868 -0.2318 0.150 Uiso 1 1 calc R . .
H3C H 0.5306 1.6159 -0.2144 0.150 Uiso 1 1 calc R . .
C4 C 0.8759(6) 1.5074(5) -0.1550(3) 0.0739(19) Uani 1 1 d . . .
H4A H 0.9355 1.4529 -0.1075 0.111 Uiso 1 1 calc R . .
H4B H 0.8778 1.5893 -0.1677 0.111 Uiso 1 1 calc R . .
H4C H 0.9098 1.4756 -0.1956 0.111 Uiso 1 1 calc R . .
C5 C 1.1005(5) 0.6918(4) 0.5523(3) 0.0369(12) Uani 1 1 d . . .
C6 C 0.9977(5) 0.8097(4) 0.5397(3) 0.0450(13) Uani 1 1 d . . .
H6 H 0.9735 0.8696 0.4903 0.054 Uiso 1 1 calc R . .
C7 C 0.9316(5) 0.8374(5) 0.6008(3) 0.0568(15) Uani 1 1 d . . .
H7 H 0.8624 0.9162 0.5924 0.068 Uiso 1 1 calc R . .
C8 C 0.9670(6) 0.7502(6) 0.6736(3) 0.0687(18) Uani 1 1 d . . .
H8 H 0.9198 0.7686 0.7142 0.082 Uiso 1 1 calc R . .
C9 C 1.0723(6) 0.6355(5) 0.6866(3) 0.0606(16) Uani 1 1 d . . .
H9 H 1.0966 0.5769 0.7364 0.073 Uiso 1 1 calc R . .
C10 C 1.1442(5) 0.6045(4) 0.6263(3) 0.0433(13) Uani 1 1 d . . .
C11 C 1.2721(6) 0.4842(4) 0.6381(3) 0.0497(14) Uani 1 1 d . . .
C12 C 1.2569(4) 0.4382(4) 0.5729(3) 0.0369(11) Uani 1 1 d . . .
C13 C 1.2918(5) 0.3142(4) 0.5810(3) 0.0437(13) Uani 1 1 d . . .
H13 H 1.3208 0.2532 0.6300 0.052 Uiso 1 1 calc R . .
C14 C 1.2841(5) 0.2796(4) 0.5176(3) 0.0505(14) Uani 1 1 d . . .
H14 H 1.3098 0.1957 0.5241 0.061 Uiso 1 1 calc R . .
C15 C 1.2391(5) 0.3679(4) 0.4457(3) 0.0532(14) Uani 1 1 d . . .
H15 H 1.2334 0.3441 0.4034 0.064 Uiso 1 1 calc R . .
C16 C 1.2017(4) 0.4927(4) 0.4354(3) 0.0402(12) Uani 1 1 d . . .
H16 H 1.1726 0.5526 0.3861 0.048 Uiso 1 1 calc R . .
C17 C 1.2080(4) 0.5283(4) 0.4991(2) 0.0324(11) Uani 1 1 d . . .
C18 C 0.9894(4) 0.9051(3) 0.3035(2) 0.0257(10) Uani 1 1 d . . .
C19 C 1.0115(4) 0.8039(4) 0.3702(2) 0.0288(10) Uani 1 1 d . . .
H19 H 0.9409 0.7726 0.3845 0.035 Uiso 1 1 calc R . .
C20 C 1.1409(4) 0.7497(4) 0.4156(2) 0.0285(10) Uani 1 1 d . . .
C21 C 1.2495(4) 0.7928(4) 0.3925(2) 0.0297(10) Uani 1 1 d . . .
H21 H 1.3367 0.7541 0.4226 0.036 Uiso 1 1 calc R . .
C22 C 1.2276(4) 0.8931(4) 0.3249(2) 0.0283(10) Uani 1 1 d . . .
H22 H 1.3000 0.9216 0.3092 0.034 Uiso 1 1 calc R . .
C23 C 1.0960(4) 0.9510(4) 0.2803(2) 0.0233(9) Uani 1 1 d . . .
C24 C 1.0393(4) 1.0620(4) 0.2105(2) 0.0257(10) Uani 1 1 d . . .
C25 C 1.1034(4) 1.1364(4) 0.1604(2) 0.0292(10) Uani 1 1 d . . .
H25 H 1.1976 1.1230 0.1716 0.035 Uiso 1 1 calc R . .
C26 C 1.0237(4) 1.2302(4) 0.0938(2) 0.0280(10) Uani 1 1 d . . .
H26 H 1.0658 1.2786 0.0595 0.034 Uiso 1 1 calc R . .
C27 C 0.8822(4) 1.2530(4) 0.0775(2) 0.0281(10) Uani 1 1 d . . .
C28 C 0.8158(4) 1.1850(3) 0.1292(2) 0.0275(10) Uani 1 1 d . . .
H28 H 0.7193 1.2041 0.1201 0.033 Uiso 1 1 calc R . .
C29 C 0.8954(4) 1.0882(4) 0.1946(2) 0.0257(10) Uani 1 1 d . . .
C30 C 0.8503(4) 0.9886(4) 0.2509(2) 0.0276(10) Uani 1 1 d . . .
C31 C 0.7379(5) 1.0398(4) 0.2986(3) 0.0352(11) Uani 1 1 d . . .
C32 C 0.7698(5) 1.0871(4) 0.3513(3) 0.0496(14) Uani 1 1 d . . .
H32 H 0.8581 1.0922 0.3544 0.059 Uiso 1 1 calc R . .
C33 C 0.6724(6) 1.1270(4) 0.3996(3) 0.0612(16) Uani 1 1 d . . .
H33 H 0.6943 1.1590 0.4348 0.073 Uiso 1 1 calc R . .
C34 C 0.5391(6) 1.1180(5) 0.3940(3) 0.0667(18) Uani 1 1 d . . .
H34 H 0.4732 1.1421 0.4268 0.080 Uiso 1 1 calc R . .
C35 C 0.5068(5) 1.0745(5) 0.3411(3) 0.0592(16) Uani 1 1 d . . .
H35 H 0.4182 1.0700 0.3376 0.071 Uiso 1 1 calc R . .
C36 C 0.6029(5) 1.0367(4) 0.2923(3) 0.0416(13) Uani 1 1 d . . .
C37 C 0.5602(5) 0.9956(4) 0.2331(3) 0.0498(14) Uani 1 1 d . . .
C38 C 0.6670(5) 0.9422(4) 0.1874(3) 0.0398(12) Uani 1 1 d . . .
C39 C 0.6274(6) 0.9026(5) 0.1308(3) 0.0549(15) Uani 1 1 d . . .
H39 H 0.5335 0.9134 0.1216 0.066 Uiso 1 1 calc R . .
C40 C 0.7263(7) 0.8483(5) 0.0893(3) 0.0647(16) Uani 1 1 d . . .
H40 H 0.6991 0.8258 0.0504 0.078 Uiso 1 1 calc R . .
C41 C 0.8656(6) 0.8273(4) 0.1054(3) 0.0552(14) Uani 1 1 d . . .
H41 H 0.9334 0.7867 0.0788 0.066 Uiso 1 1 calc R . .
C42 C 0.9067(5) 0.8656(4) 0.1604(3) 0.0416(12) Uani 1 1 d . . .
H42 H 1.0019 0.8506 0.1701 0.050 Uiso 1 1 calc R . .
C43 C 0.8081(4) 0.9264(4) 0.2018(2) 0.0309(11) Uani 1 1 d . . .
C44 C 0.7757(4) 1.2989(4) -0.0522(2) 0.0316(11) Uani 1 1 d . . .
C45 C 0.7950(5) 1.1743(4) -0.0354(3) 0.0423(12) Uani 1 1 d . . .
H45 H 0.8367 1.1162 0.0133 0.051 Uiso 1 1 calc R . .
C46 C 0.7528(5) 1.1362(5) -0.0901(3) 0.0532(14) Uani 1 1 d . . .
H46 H 0.7652 1.0529 -0.0777 0.064 Uiso 1 1 calc R . .
C47 C 0.6933(5) 1.2190(5) -0.1620(3) 0.0531(14) Uani 1 1 d . . .
H47 H 0.6624 1.1931 -0.1980 0.064 Uiso 1 1 calc R . .
C48 C 0.6791(5) 1.3430(5) -0.1813(3) 0.0494(13) Uani 1 1 d . . .
H48 H 0.6414 1.3992 -0.2309 0.059 Uiso 1 1 calc R . .
C49 C 0.7209(5) 1.3838(4) -0.1267(2) 0.0374(11) Uani 1 1 d . . .
C50 C 0.7215(5) 1.5146(4) -0.1454(3) 0.0497(14) Uani 1 1 d . . .
C51 C 0.6767(4) 1.5555(4) -0.0765(3) 0.0362(11) Uani 1 1 d . . .
C52 C 0.5929(5) 1.6765(4) -0.0828(3) 0.0487(13) Uani 1 1 d . . .
H52 H 0.5557 1.7360 -0.1316 0.058 Uiso 1 1 calc R . .
C53 C 0.5626(5) 1.7119(4) -0.0185(3) 0.0475(13) Uani 1 1 d . . .
H53 H 0.5071 1.7940 -0.0241 0.057 Uiso 1 1 calc R . .
C54 C 0.6166(5) 1.6226(4) 0.0540(3) 0.0508(14) Uani 1 1 d . . .
H54 H 0.5972 1.6446 0.0977 0.061 Uiso 1 1 calc R . .
C55 C 0.6985(5) 1.5020(4) 0.0618(3) 0.0428(12) Uani 1 1 d . . .
H55 H 0.7347 1.4428 0.1108 0.051 Uiso 1 1 calc R . .
C56 C 0.7279(4) 1.4670(4) -0.0032(2) 0.0302(10) Uani 1 1 d . . .
N1 N 1.1635(3) 0.6550(3) 0.49054(19) 0.0307(9) Uani 1 1 d . . .
N2 N 0.8081(4) 1.3425(3) 0.0041(2) 0.0327(9) Uani 1 1 d . . .
O1 O 0.4354(3) 1.0072(4) 0.2230(2) 0.0846(14) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C11 1.537(6) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C11 1.563(6) . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C3 C50 1.532(6) . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?
C4 C50 1.556(6) . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C5 C10 1.386(6) . ?
C5 C6 1.389(5) . ?
C5 N1 1.422(5) . ?
C6 C7 1.380(6) . ?
C6 H6 0.9300 . ?
C7 C8 1.366(7) . ?
C7 H7 0.9300 . ?
C8 C9 1.372(7) . ?
C8 H8 0.9300 . ?
C9 C10 1.402(6) . ?
C9 H9 0.9300 . ?
C10 C11 1.526(6) . ?
C11 C12 1.521(6) . ?
C12 C13 1.385(5) . ?
C12 C17 1.399(5) . ?
C13 C14 1.385(6) . ?
C13 H13 0.9300 . ?
C14 C15 1.362(6) . ?
C14 H14 0.9300 . ?
C15 C16 1.381(5) . ?
C15 H15 0.9300 . ?
C16 C17 1.394(5) . ?
C16 H16 0.9300 . ?
C17 N1 1.406(5) . ?
C18 C19 1.378(5) . ?
C18 C23 1.397(5) . ?
C18 C30 1.531(5) . ?
C19 C20 1.387(5) . ?
C19 H19 0.9300 . ?
C20 C21 1.395(5) . ?
C20 N1 1.438(5) . ?
C21 C22 1.383(5) . ?
C21 H21 0.9300 . ?
C22 C23 1.396(5) . ?
C22 H22 0.9300 . ?
C23 C24 1.463(5) . ?
C24 C29 1.398(5) . ?
C24 C25 1.402(5) . ?
C25 C26 1.384(5) . ?
C25 H25 0.9300 . ?
C26 C27 1.385(5) . ?
C26 H26 0.9300 . ?
C27 C28 1.388(5) . ?
C27 N2 1.436(5) . ?
C28 C29 1.384(5) . ?
C28 H28 0.9300 . ?
C29 C30 1.527(5) . ?
C30 C31 1.513(5) . ?
C30 C43 1.517(5) . ?
C31 C32 1.383(6) . ?
C31 C36 1.401(6) . ?
C32 C33 1.388(6) . ?
C32 H32 0.9300 . ?
C33 C34 1.412(7) . ?
C33 H33 0.9300 . ?
C34 C35 1.355(7) . ?
C34 H34 0.9300 . ?
C35 C36 1.378(6) . ?
C35 H35 0.9300 . ?
C36 C37 1.478(7) . ?
C37 O1 1.240(5) . ?
C37 C38 1.463(6) . ?
C38 C43 1.400(5) . ?
C38 C39 1.411(6) . ?
C39 C40 1.366(7) . ?
C39 H39 0.9300 . ?
C40 C41 1.369(6) . ?
C40 H40 0.9300 . ?
C41 C42 1.380(6) . ?
C41 H41 0.9300 . ?
C42 C43 1.399(5) . ?
C42 H42 0.9300 . ?
C44 C45 1.392(5) . ?
C44 C49 1.395(6) . ?
C44 N2 1.411(5) . ?
C45 C46 1.379(6) . ?
C45 H45 0.9300 . ?
C46 C47 1.362(6) . ?
C46 H46 0.9300 . ?
C47 C48 1.394(6) . ?
C47 H47 0.9300 . ?
C48 C49 1.399(6) . ?
C48 H48 0.9300 . ?
C49 C50 1.527(6) . ?
C50 C51 1.521(6) . ?
C51 C52 1.385(5) . ?
C51 C56 1.387(5) . ?
C52 C53 1.386(6) . ?
C52 H52 0.9300 . ?
C53 C54 1.384(6) . ?
C53 H53 0.9300 . ?
C54 C55 1.367(6) . ?
C54 H54 0.9300 . ?
C55 C56 1.396(5) . ?
C55 H55 0.9300 . ?
C56 N2 1.408(5) . ?

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
C11 C1 H1A 109.5 . . ?
C11 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C11 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C11 C2 H2A 109.5 . . ?
C11 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
C11 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C50 C3 H3A 109.5 . . ?
C50 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C50 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C50 C4 H4A 109.5 . . ?
C50 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C50 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C10 C5 C6 120.7(4) . . ?
C10 C5 N1 117.3(4) . . ?
C6 C5 N1 121.9(4) . . ?
C7 C6 C5 119.6(5) . . ?
C7 C6 H6 120.2 . . ?
C5 C6 H6 120.2 . . ?
C8 C7 C6 120.6(5) . . ?
C8 C7 H7 119.7 . . ?
C6 C7 H7 119.7 . . ?
C7 C8 C9 119.8(5) . . ?
C7 C8 H8 120.1 . . ?
C9 C8 H8 120.1 . . ?
C8 C9 C10 121.4(5) . . ?
C8 C9 H9 119.3 . . ?
C10 C9 H9 119.3 . . ?
C5 C10 C9 117.6(5) . . ?
C5 C10 C11 118.3(4) . . ?
C9 C10 C11 124.0(5) . . ?
C12 C11 C10 107.6(4) . . ?
C12 C11 C1 112.0(4) . . ?
C10 C11 C1 113.2(4) . . ?
C12 C11 C2 108.3(4) . . ?
C10 C11 C2 107.9(4) . . ?
C1 C11 C2 107.7(4) . . ?
C13 C12 C17 118.0(4) . . ?
C13 C12 C11 124.9(4) . . ?
C17 C12 C11 117.0(4) . . ?
C14 C13 C12 121.2(4) . . ?
C14 C13 H13 119.4 . . ?
C12 C13 H13 119.4 . . ?
C15 C14 C13 120.2(4) . . ?
C15 C14 H14 119.9 . . ?
C13 C14 H14 119.9 . . ?
C14 C15 C16 120.4(5) . . ?
C14 C15 H15 119.8 . . ?
C16 C15 H15 119.8 . . ?
C15 C16 C17 119.7(4) . . ?
C15 C16 H16 120.1 . . ?
C17 C16 H16 120.1 . . ?
C16 C17 C12 120.4(4) . . ?
C16 C17 N1 120.8(4) . . ?
C12 C17 N1 118.8(4) . . ?
C19 C18 C23 121.1(4) . . ?
C19 C18 C30 127.5(4) . . ?
C23 C18 C30 111.2(3) . . ?
C18 C19 C20 118.9(4) . . ?
C18 C19 H19 120.5 . . ?
C20 C19 H19 120.5 . . ?
C19 C20 C21 120.7(4) . . ?
C19 C20 N1 121.3(4) . . ?
C21 C20 N1 117.9(4) . . ?
C22 C21 C20 120.2(4) . . ?
C22 C21 H21 119.9 . . ?
C20 C21 H21 119.9 . . ?
C21 C22 C23 119.5(4) . . ?
C21 C22 H22 120.2 . . ?
C23 C22 H22 120.2 . . ?
C22 C23 C18 119.6(4) . . ?
C22 C23 C24 131.7(4) . . ?
C18 C23 C24 108.6(4) . . ?
C29 C24 C25 119.7(4) . . ?
C29 C24 C23 108.2(3) . . ?
C25 C24 C23 132.0(4) . . ?
C26 C25 C24 118.6(4) . . ?
C26 C25 H25 120.7 . . ?
C24 C25 H25 120.7 . . ?
C25 C26 C27 121.2(4) . . ?
C25 C26 H26 119.4 . . ?
C27 C26 H26 119.4 . . ?
C26 C27 C28 120.4(4) . . ?
C26 C27 N2 118.9(4) . . ?
C28 C27 N2 120.5(4) . . ?
C29 C28 C27 118.9(4) . . ?
C29 C28 H28 120.6 . . ?
C27 C28 H28 120.6 . . ?
C28 C29 C24 120.9(4) . . ?
C28 C29 C30 127.1(4) . . ?
C24 C29 C30 111.4(3) . . ?
C31 C30 C43 114.8(3) . . ?
C31 C30 C29 113.1(3) . . ?
C43 C30 C29 105.3(3) . . ?
C31 C30 C18 109.1(4) . . ?
C43 C30 C18 113.3(3) . . ?
C29 C30 C18 100.4(3) . . ?
C32 C31 C36 119.0(4) . . ?
C32 C31 C30 119.7(4) . . ?
C36 C31 C30 121.3(4) . . ?
C31 C32 C33 121.2(5) . . ?
C31 C32 H32 119.4 . . ?
C33 C32 H32 119.4 . . ?
C32 C33 C34 118.4(5) . . ?
C32 C33 H33 120.8 . . ?
C34 C33 H33 120.8 . . ?
C35 C34 C33 120.3(5) . . ?
C35 C34 H34 119.8 . . ?
C33 C34 H34 119.8 . . ?
C34 C35 C36 121.2(5) . . ?
C34 C35 H35 119.4 . . ?
C36 C35 H35 119.4 . . ?
C35 C36 C31 119.8(5) . . ?
C35 C36 C37 119.1(5) . . ?
C31 C36 C37 121.0(4) . . ?
O1 C37 C38 121.5(5) . . ?
O1 C37 C36 119.6(5) . . ?
C38 C37 C36 118.9(4) . . ?
C43 C38 C39 120.3(5) . . ?
C43 C38 C37 120.3(5) . . ?
C39 C38 C37 119.3(5) . . ?
C40 C39 C38 120.4(5) . . ?
C40 C39 H39 119.8 . . ?
C38 C39 H39 119.8 . . ?
C39 C40 C41 119.7(6) . . ?
C39 C40 H40 120.2 . . ?
C41 C40 H40 120.2 . . ?
C40 C41 C42 120.8(5) . . ?
C40 C41 H41 119.6 . . ?
C42 C41 H41 119.6 . . ?
C41 C42 C43 121.4(5) . . ?
C41 C42 H42 119.3 . . ?
C43 C42 H42 119.3 . . ?
C42 C43 C38 117.3(4) . . ?
C42 C43 C30 120.4(4) . . ?
C38 C43 C30 121.8(4) . . ?
C45 C44 C49 119.2(4) . . ?
C45 C44 N2 122.0(4) . . ?
C49 C44 N2 118.8(4) . . ?
C46 C45 C44 120.6(5) . . ?
C46 C45 H45 119.7 . . ?
C44 C45 H45 119.7 . . ?
C47 C46 C45 120.8(5) . . ?
C47 C46 H46 119.6 . . ?
C45 C46 H46 119.6 . . ?
C46 C47 C48 119.5(5) . . ?
C46 C47 H47 120.3 . . ?
C48 C47 H47 120.3 . . ?
C47 C48 C49 120.6(5) . . ?
C47 C48 H48 119.7 . . ?
C49 C48 H48 119.7 . . ?
C44 C49 C48 119.0(4) . . ?
C44 C49 C50 117.2(4) . . ?
C48 C49 C50 123.6(4) . . ?
C51 C50 C49 108.0(4) . . ?
C51 C50 C3 112.2(4) . . ?
C49 C50 C3 111.9(4) . . ?
C51 C50 C4 107.5(4) . . ?
C49 C50 C4 108.5(4) . . ?
C3 C50 C4 108.5(4) . . ?
C52 C51 C56 118.3(4) . . ?
C52 C51 C50 123.8(4) . . ?
C56 C51 C50 117.8(4) . . ?
C51 C52 C53 122.1(5) . . ?
C51 C52 H52 119.0 . . ?
C53 C52 H52 119.0 . . ?
C54 C53 C52 118.6(4) . . ?
C54 C53 H53 120.7 . . ?
C52 C53 H53 120.7 . . ?
C55 C54 C53 120.5(5) . . ?
C55 C54 H54 119.8 . . ?
C53 C54 H54 119.8 . . ?
C54 C55 C56 120.5(4) . . ?
C54 C55 H55 119.7 . . ?
C56 C55 H55 119.7 . . ?
C51 C56 C55 120.0(4) . . ?
C51 C56 N2 118.8(4) . . ?
C55 C56 N2 121.2(4) . . ?
C17 N1 C5 117.9(3) . . ?
C17 N1 C20 121.1(3) . . ?
C5 N1 C20 118.4(3) . . ?
C56 N2 C44 117.5(4) . . ?
C56 N2 C27 120.3(3) . . ?
C44 N2 C27 118.7(3) . . ?

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
C10 C5 C6 C7 -4.3(7) . . . . ?
N1 C5 C6 C7 174.8(4) . . . . ?
C5 C6 C7 C8 0.3(7) . . . . ?
C6 C7 C8 C9 2.2(8) . . . . ?
C7 C8 C9 C10 -0.8(8) . . . . ?
C6 C5 C10 C9 5.6(7) . . . . ?
N1 C5 C10 C9 -173.6(4) . . . . ?
C6 C5 C10 C11 -171.1(4) . . . . ?
N1 C5 C10 C11 9.8(6) . . . . ?
C8 C9 C10 C5 -3.1(7) . . . . ?
C8 C9 C10 C11 173.4(4) . . . . ?
C5 C10 C11 C12 -43.3(5) . . . . ?
C9 C10 C11 C12 140.3(4) . . . . ?
C5 C10 C11 C1 -167.5(4) . . . . ?
C9 C10 C11 C1 16.0(6) . . . . ?
C5 C10 C11 C2 73.4(5) . . . . ?
C9 C10 C11 C2 -103.0(5) . . . . ?
C10 C11 C12 C13 -141.1(4) . . . . ?
C1 C11 C12 C13 -16.1(7) . . . . ?
C2 C11 C12 C13 102.5(5) . . . . ?
C10 C11 C12 C17 41.0(5) . . . . ?
C1 C11 C12 C17 165.9(4) . . . . ?
C2 C11 C12 C17 -75.5(5) . . . . ?
C17 C12 C13 C14 2.6(6) . . . . ?
C11 C12 C13 C14 -175.3(4) . . . . ?
C12 C13 C14 C15 -1.3(7) . . . . ?
C13 C14 C15 C16 0.6(7) . . . . ?
C14 C15 C16 C17 -1.1(7) . . . . ?
C15 C16 C17 C12 2.4(6) . . . . ?
C15 C16 C17 N1 -176.6(4) . . . . ?
C13 C12 C17 C16 -3.1(6) . . . . ?
C11 C12 C17 C16 175.0(4) . . . . ?
C13 C12 C17 N1 175.9(4) . . . . ?
C11 C12 C17 N1 -6.0(6) . . . . ?
C23 C18 C19 C20 1.8(6) . . . . ?
C30 C18 C19 C20 -171.7(4) . . . . ?
C18 C19 C20 C21 -3.0(6) . . . . ?
C18 C19 C20 N1 171.6(3) . . . . ?
C19 C20 C21 C22 1.9(6) . . . . ?
N1 C20 C21 C22 -172.9(3) . . . . ?
C20 C21 C22 C23 0.4(6) . . . . ?
C21 C22 C23 C18 -1.5(6) . . . . ?
C21 C22 C23 C24 175.0(4) . . . . ?
C19 C18 C23 C22 0.4(6) . . . . ?
C30 C18 C23 C22 174.9(3) . . . . ?
C19 C18 C23 C24 -176.9(4) . . . . ?
C30 C18 C23 C24 -2.4(4) . . . . ?
C22 C23 C24 C29 -172.8(4) . . . . ?
C18 C23 C24 C29 4.0(4) . . . . ?
C22 C23 C24 C25 9.6(7) . . . . ?
C18 C23 C24 C25 -173.6(4) . . . . ?
C29 C24 C25 C26 -3.6(6) . . . . ?
C23 C24 C25 C26 173.8(4) . . . . ?
C24 C25 C26 C27 1.7(6) . . . . ?
C25 C26 C27 C28 2.4(6) . . . . ?
C25 C26 C27 N2 -173.7(4) . . . . ?
C26 C27 C28 C29 -4.5(6) . . . . ?
N2 C27 C28 C29 171.5(4) . . . . ?
C27 C28 C29 C24 2.6(6) . . . . ?
C27 C28 C29 C30 -168.5(4) . . . . ?
C25 C24 C29 C28 1.4(6) . . . . ?
C23 C24 C29 C28 -176.5(4) . . . . ?
C25 C24 C29 C30 173.8(3) . . . . ?
C23 C24 C29 C30 -4.2(4) . . . . ?
C28 C29 C30 C31 -69.5(6) . . . . ?
C24 C29 C30 C31 118.7(4) . . . . ?
C28 C29 C30 C43 56.6(5) . . . . ?
C24 C29 C30 C43 -115.2(4) . . . . ?
C28 C29 C30 C18 174.4(4) . . . . ?
C24 C29 C30 C18 2.6(4) . . . . ?
C19 C18 C30 C31 54.9(5) . . . . ?
C23 C18 C30 C31 -119.1(3) . . . . ?
C19 C18 C30 C43 -74.2(5) . . . . ?
C23 C18 C30 C43 111.7(4) . . . . ?
C19 C18 C30 C29 174.0(4) . . . . ?
C23 C18 C30 C29 -0.1(4) . . . . ?
C43 C30 C31 C32 173.5(4) . . . . ?
C29 C30 C31 C32 -65.6(5) . . . . ?
C18 C30 C31 C32 45.2(5) . . . . ?
C43 C30 C31 C36 -4.3(5) . . . . ?
C29 C30 C31 C36 116.5(4) . . . . ?
C18 C30 C31 C36 -132.7(4) . . . . ?
C36 C31 C32 C33 2.3(7) . . . . ?
C30 C31 C32 C33 -175.6(4) . . . . ?
C31 C32 C33 C34 0.2(7) . . . . ?
C32 C33 C34 C35 -1.8(8) . . . . ?
C33 C34 C35 C36 0.8(8) . . . . ?
C34 C35 C36 C31 1.7(7) . . . . ?
C34 C35 C36 C37 -177.1(4) . . . . ?
C32 C31 C36 C35 -3.2(6) . . . . ?
C30 C31 C36 C35 174.6(4) . . . . ?
C32 C31 C36 C37 175.5(4) . . . . ?
C30 C31 C36 C37 -6.6(6) . . . . ?
C35 C36 C37 O1 7.0(6) . . . . ?
C31 C36 C37 O1 -171.8(4) . . . . ?
C35 C36 C37 C38 -173.1(4) . . . . ?
C31 C36 C37 C38 8.1(6) . . . . ?
O1 C37 C38 C43 -177.9(4) . . . . ?
C36 C37 C38 C43 2.2(6) . . . . ?
O1 C37 C38 C39 -0.2(7) . . . . ?
C36 C37 C38 C39 179.9(4) . . . . ?
C43 C38 C39 C40 0.0(7) . . . . ?
C37 C38 C39 C40 -177.7(4) . . . . ?
C38 C39 C40 C41 3.0(8) . . . . ?
C39 C40 C41 C42 -3.1(8) . . . . ?
C40 C41 C42 C43 0.3(7) . . . . ?
C41 C42 C43 C38 2.6(6) . . . . ?
C41 C42 C43 C30 -168.7(4) . . . . ?
C39 C38 C43 C42 -2.7(6) . . . . ?
C37 C38 C43 C42 174.9(4) . . . . ?
C39 C38 C43 C30 168.5(4) . . . . ?
C37 C38 C43 C30 -13.9(6) . . . . ?
C31 C30 C43 C42 -174.3(4) . . . . ?
C29 C30 C43 C42 60.6(5) . . . . ?
C18 C30 C43 C42 -48.1(5) . . . . ?
C31 C30 C43 C38 14.8(5) . . . . ?
C29 C30 C43 C38 -110.3(4) . . . . ?
C18 C30 C43 C38 141.0(4) . . . . ?
C49 C44 C45 C46 -3.9(7) . . . . ?
N2 C44 C45 C46 175.3(4) . . . . ?
C44 C45 C46 C47 1.0(7) . . . . ?
C45 C46 C47 C48 2.1(7) . . . . ?
C46 C47 C48 C49 -2.2(7) . . . . ?
C45 C44 C49 C48 3.7(6) . . . . ?
N2 C44 C49 C48 -175.5(4) . . . . ?
C45 C44 C49 C50 -171.4(4) . . . . ?
N2 C44 C49 C50 9.4(6) . . . . ?
C47 C48 C49 C44 -0.7(7) . . . . ?
C47 C48 C49 C50 174.1(4) . . . . ?
C44 C49 C50 C51 -41.8(5) . . . . ?
C48 C49 C50 C51 143.3(4) . . . . ?
C44 C49 C50 C3 -165.8(4) . . . . ?
C48 C49 C50 C3 19.3(7) . . . . ?
C44 C49 C50 C4 74.4(5) . . . . ?
C48 C49 C50 C4 -100.4(5) . . . . ?
C49 C50 C51 C52 -142.8(4) . . . . ?
C3 C50 C51 C52 -19.0(7) . . . . ?
C4 C50 C51 C52 100.3(5) . . . . ?
C49 C50 C51 C56 39.9(6) . . . . ?
C3 C50 C51 C56 163.7(5) . . . . ?
C4 C50 C51 C56 -77.0(5) . . . . ?
C56 C51 C52 C53 1.9(7) . . . . ?
C50 C51 C52 C53 -175.4(4) . . . . ?
C51 C52 C53 C54 -0.9(7) . . . . ?
C52 C53 C54 C55 0.1(7) . . . . ?
C53 C54 C55 C56 -0.4(7) . . . . ?
C52 C51 C56 C55 -2.1(6) . . . . ?
C50 C51 C56 C55 175.3(4) . . . . ?
C52 C51 C56 N2 177.2(4) . . . . ?
C50 C51 C56 N2 -5.3(6) . . . . ?
C54 C55 C56 C51 1.4(7) . . . . ?
C54 C55 C56 N2 -177.9(4) . . . . ?
C16 C17 N1 C5 146.9(4) . . . . ?
C12 C17 N1 C5 -32.1(6) . . . . ?
C16 C17 N1 C20 -14.3(6) . . . . ?
C12 C17 N1 C20 166.7(4) . . . . ?
C10 C5 N1 C17 30.0(6) . . . . ?
C6 C5 N1 C17 -149.1(4) . . . . ?
C10 C5 N1 C20 -168.3(4) . . . . ?
C6 C5 N1 C20 12.6(6) . . . . ?
C19 C20 N1 C17 87.3(5) . . . . ?
C21 C20 N1 C17 -97.9(4) . . . . ?
C19 C20 N1 C5 -73.7(5) . . . . ?
C21 C20 N1 C5 101.0(4) . . . . ?
C51 C56 N2 C44 -31.6(5) . . . . ?
C55 C56 N2 C44 147.7(4) . . . . ?
C51 C56 N2 C27 169.6(4) . . . . ?
C55 C56 N2 C27 -11.0(6) . . . . ?
C45 C44 N2 C56 -149.8(4) . . . . ?
C49 C44 N2 C56 29.4(5) . . . . ?
C45 C44 N2 C27 9.3(6) . . . . ?
C49 C44 N2 C27 -171.6(4) . . . . ?
C26 C27 N2 C56 -95.2(5) . . . . ?
C28 C27 N2 C56 88.7(5) . . . . ?
C26 C27 N2 C44 106.3(4) . . . . ?
C28 C27 N2 C44 -69.7(5) . . . . ?

_diffrn_measured_fraction_theta_max 0.968
_diffrn_reflns_theta_full        26.39
_diffrn_measured_fraction_theta_full 0.968
_refine_diff_density_max         0.243
_refine_diff_density_min         -0.290
_refine_diff_density_rms         0.051
