# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1
_audit_block_doi                 10.5517/ccdc.csd.cc1p2yxm
_database_code_depnum_ccdc_archive 'CCDC 1551981'
_audit_update_record             
;
2017-05-24 deposited with the CCDC.
2017-08-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        3-(anthracen-9-yl)-N,N-diphenylaniline
_chemical_name_common            ?
_chemical_melting_point          454
_chemical_formula_moiety         'C32 H23 N'
_chemical_formula_sum            'C32 H23 N'
_chemical_formula_weight         421.51

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

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

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

_cell_length_a                   18.1663(17)
_cell_length_b                   29.653(3)
_cell_length_c                   8.5668(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     4614.9(8)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    34160
_cell_measurement_theta_min      3.01
_cell_measurement_theta_max      27.44

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.213
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1776
_exptl_absorpt_coefficient_mu    0.070
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9903
_exptl_absorpt_correction_T_max  0.9924
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            32058
_diffrn_reflns_av_R_equivalents  0.0886
_diffrn_reflns_av_sigmaI/netI    0.0622
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_k_max       39
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         1.37
_diffrn_reflns_theta_max         28.28
_reflns_number_total             5743
_reflns_number_gt                2729
_reflns_threshold_expression     >2sigma(I)

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

_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)+(0.0779P)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     SHELXL
_refine_ls_extinction_coef       0.0068(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         5743
_refine_ls_number_parameters     299
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1399
_refine_ls_R_factor_gt           0.0540
_refine_ls_wR_factor_ref         0.1648
_refine_ls_wR_factor_gt          0.1162
_refine_ls_goodness_of_fit_ref   0.967
_refine_ls_restrained_S_all      0.967
_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 0.13901(10) 0.49882(6) 0.5574(2) 0.0388(5) Uani 1 1 d . . .
C2 C 0.18015(11) 0.46803(7) 0.6432(2) 0.0455(5) Uani 1 1 d . . .
H2 H 0.1959 0.4414 0.5964 0.055 Uiso 1 1 calc R . .
C3 C 0.19793(11) 0.47654(8) 0.7969(2) 0.0533(6) Uani 1 1 d . . .
H3 H 0.2244 0.4552 0.8533 0.064 Uiso 1 1 calc R . .
C4 C 0.17703(13) 0.51611(8) 0.8680(3) 0.0591(6) Uani 1 1 d . . .
H4 H 0.1890 0.5217 0.9717 0.071 Uiso 1 1 calc R . .
C5 C 0.13822(13) 0.54713(8) 0.7827(2) 0.0562(6) Uani 1 1 d . . .
H5 H 0.1248 0.5743 0.8288 0.067 Uiso 1 1 calc R . .
C6 C 0.11858(11) 0.53883(7) 0.6295(2) 0.0485(5) Uani 1 1 d . . .
H6 H 0.0915 0.5602 0.5744 0.058 Uiso 1 1 calc R . .
C7 C 0.09855(11) 0.52539(6) 0.2994(2) 0.0399(5) Uani 1 1 d . . .
C8 C 0.14307(12) 0.56324(6) 0.2852(2) 0.0510(5) Uani 1 1 d . . .
H8 H 0.1879 0.5644 0.3377 0.061 Uiso 1 1 calc R . .
C9 C 0.12120(15) 0.59904(7) 0.1938(3) 0.0621(7) Uani 1 1 d . . .
H9 H 0.1511 0.6244 0.1861 0.074 Uiso 1 1 calc R . .
C10 C 0.05568(16) 0.59763(8) 0.1141(3) 0.0666(7) Uani 1 1 d . . .
H10 H 0.0406 0.6221 0.0544 0.080 Uiso 1 1 calc R . .
C11 C 0.01256(13) 0.55964(9) 0.1236(3) 0.0642(7) Uani 1 1 d . . .
H11 H -0.0311 0.5581 0.0670 0.077 Uiso 1 1 calc R . .
C12 C 0.03339(12) 0.52377(7) 0.2161(2) 0.0508(5) Uani 1 1 d . . .
H12 H 0.0035 0.4984 0.2225 0.061 Uiso 1 1 calc R . .
C13 C 0.10506(10) 0.44431(6) 0.3543(2) 0.0396(5) Uani 1 1 d . . .
C14 C 0.12581(11) 0.42982(7) 0.2062(2) 0.0469(5) Uani 1 1 d . . .
H14 H 0.1472 0.4500 0.1367 0.056 Uiso 1 1 calc R . .
C15 C 0.11487(12) 0.38573(7) 0.1621(2) 0.0524(6) Uani 1 1 d . . .
H15 H 0.1282 0.3766 0.0621 0.063 Uiso 1 1 calc R . .
C16 C 0.08450(12) 0.35498(7) 0.2638(2) 0.0514(5) Uani 1 1 d . . .
H16 H 0.0784 0.3251 0.2333 0.062 Uiso 1 1 calc R . .
C17 C 0.06306(11) 0.36865(6) 0.4121(2) 0.0429(5) Uani 1 1 d . . .
C18 C 0.07269(10) 0.41344(6) 0.4547(2) 0.0413(5) Uani 1 1 d . . .
H18 H 0.0571 0.4229 0.5527 0.050 Uiso 1 1 calc R . .
C19 C 0.03000(12) 0.33690(6) 0.5280(2) 0.0463(5) Uani 1 1 d . . .
C20 C -0.04440(13) 0.32491(6) 0.5157(3) 0.0518(6) Uani 1 1 d . . .
C21 C -0.09072(13) 0.34089(7) 0.3938(3) 0.0631(7) Uani 1 1 d . . .
H21 H -0.0709 0.3591 0.3160 0.076 Uiso 1 1 calc R . .
C22 C -0.16324(15) 0.33014(9) 0.3888(4) 0.0822(8) Uani 1 1 d . . .
H22 H -0.1925 0.3414 0.3088 0.099 Uiso 1 1 calc R . .
C23 C -0.19444(17) 0.30227(10) 0.5028(5) 0.0948(10) Uani 1 1 d . . .
H23 H -0.2443 0.2952 0.4979 0.114 Uiso 1 1 calc R . .
C24 C -0.15291(18) 0.28561(9) 0.6196(4) 0.0845(9) Uani 1 1 d . . .
H24 H -0.1744 0.2668 0.6936 0.101 Uiso 1 1 calc R . .
C25 C -0.07680(15) 0.29617(7) 0.6318(3) 0.0621(6) Uani 1 1 d . . .
C26 C -0.03357(17) 0.28074(7) 0.7533(3) 0.0700(7) Uani 1 1 d . . .
H26 H -0.0548 0.2621 0.8283 0.084 Uiso 1 1 calc R . .
C27 C 0.04041(16) 0.29200(7) 0.7676(3) 0.0595(6) Uani 1 1 d . . .
C28 C 0.0851(2) 0.27617(8) 0.8917(3) 0.0776(8) Uani 1 1 d . . .
H28 H 0.0641 0.2580 0.9681 0.093 Uiso 1 1 calc R . .
C29 C 0.1569(2) 0.28665(9) 0.9022(3) 0.0848(9) Uani 1 1 d . . .
H29 H 0.1847 0.2758 0.9853 0.102 Uiso 1 1 calc R . .
C30 C 0.19015(16) 0.31405(9) 0.7874(3) 0.0785(8) Uani 1 1 d . . .
H30 H 0.2400 0.3209 0.7944 0.094 Uiso 1 1 calc R . .
C31 C 0.14977(14) 0.33054(8) 0.6668(3) 0.0615(6) Uani 1 1 d . . .
H31 H 0.1725 0.3487 0.5925 0.074 Uiso 1 1 calc R . .
C32 C 0.07333(13) 0.32061(7) 0.6517(2) 0.0497(5) Uani 1 1 d . . .
N1 N 0.11827(9) 0.48952(5) 0.40154(18) 0.0430(4) 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 C6 1.388(3) . ?
C1 C2 1.390(3) . ?
C1 N1 1.415(2) . ?
C2 C3 1.379(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.375(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.370(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.382(3) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C12 1.383(3) . ?
C7 C8 1.389(3) . ?
C7 N1 1.423(2) . ?
C8 C9 1.378(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.373(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.374(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.380(3) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 C18 1.387(3) . ?
C13 C14 1.391(3) . ?
C13 N1 1.421(2) . ?
C14 C15 1.375(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.377(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.389(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.389(3) . ?
C17 C19 1.495(3) . ?
C18 H18 0.9300 . ?
C19 C20 1.401(3) . ?
C19 C32 1.405(3) . ?
C20 C21 1.423(3) . ?
C20 C25 1.436(3) . ?
C21 C22 1.356(3) . ?
C21 H21 0.9300 . ?
C22 C23 1.399(4) . ?
C22 H22 0.9300 . ?
C23 C24 1.347(4) . ?
C23 H23 0.9300 . ?
C24 C25 1.421(4) . ?
C24 H24 0.9300 . ?
C25 C26 1.382(3) . ?
C26 C27 1.390(3) . ?
C26 H26 0.9300 . ?
C27 C28 1.417(3) . ?
C27 C32 1.437(3) . ?
C28 C29 1.343(4) . ?
C28 H28 0.9300 . ?
C29 C30 1.412(4) . ?
C29 H29 0.9300 . ?
C30 C31 1.358(3) . ?
C30 H30 0.9300 . ?
C31 C32 1.425(3) . ?
C31 H31 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
C6 C1 C2 118.05(18) . . ?
C6 C1 N1 121.04(18) . . ?
C2 C1 N1 120.92(18) . . ?
C3 C2 C1 120.7(2) . . ?
C3 C2 H2 119.7 . . ?
C1 C2 H2 119.7 . . ?
C4 C3 C2 120.9(2) . . ?
C4 C3 H3 119.5 . . ?
C2 C3 H3 119.5 . . ?
C5 C4 C3 118.6(2) . . ?
C5 C4 H4 120.7 . . ?
C3 C4 H4 120.7 . . ?
C4 C5 C6 121.3(2) . . ?
C4 C5 H5 119.4 . . ?
C6 C5 H5 119.4 . . ?
C5 C6 C1 120.4(2) . . ?
C5 C6 H6 119.8 . . ?
C1 C6 H6 119.8 . . ?
C12 C7 C8 118.77(18) . . ?
C12 C7 N1 120.45(17) . . ?
C8 C7 N1 120.75(18) . . ?
C9 C8 C7 120.3(2) . . ?
C9 C8 H8 119.8 . . ?
C7 C8 H8 119.8 . . ?
C10 C9 C8 120.6(2) . . ?
C10 C9 H9 119.7 . . ?
C8 C9 H9 119.7 . . ?
C9 C10 C11 119.3(2) . . ?
C9 C10 H10 120.3 . . ?
C11 C10 H10 120.3 . . ?
C10 C11 C12 120.6(2) . . ?
C10 C11 H11 119.7 . . ?
C12 C11 H11 119.7 . . ?
C11 C12 C7 120.3(2) . . ?
C11 C12 H12 119.8 . . ?
C7 C12 H12 119.8 . . ?
C18 C13 C14 118.46(18) . . ?
C18 C13 N1 121.16(17) . . ?
C14 C13 N1 120.37(17) . . ?
C15 C14 C13 120.34(19) . . ?
C15 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?
C14 C15 C16 120.89(19) . . ?
C14 C15 H15 119.6 . . ?
C16 C15 H15 119.6 . . ?
C15 C16 C17 119.86(19) . . ?
C15 C16 H16 120.1 . . ?
C17 C16 H16 120.1 . . ?
C18 C17 C16 118.98(18) . . ?
C18 C17 C19 118.56(17) . . ?
C16 C17 C19 122.46(17) . . ?
C13 C18 C17 121.43(18) . . ?
C13 C18 H18 119.3 . . ?
C17 C18 H18 119.3 . . ?
C20 C19 C32 120.63(19) . . ?
C20 C19 C17 119.83(19) . . ?
C32 C19 C17 119.50(19) . . ?
C19 C20 C21 122.8(2) . . ?
C19 C20 C25 119.6(2) . . ?
C21 C20 C25 117.6(2) . . ?
C22 C21 C20 121.3(2) . . ?
C22 C21 H21 119.4 . . ?
C20 C21 H21 119.4 . . ?
C21 C22 C23 120.7(3) . . ?
C21 C22 H22 119.6 . . ?
C23 C22 H22 119.6 . . ?
C24 C23 C22 120.5(3) . . ?
C24 C23 H23 119.7 . . ?
C22 C23 H23 119.7 . . ?
C23 C24 C25 121.2(3) . . ?
C23 C24 H24 119.4 . . ?
C25 C24 H24 119.4 . . ?
C26 C25 C24 122.4(3) . . ?
C26 C25 C20 119.0(2) . . ?
C24 C25 C20 118.6(3) . . ?
C25 C26 C27 122.4(2) . . ?
C25 C26 H26 118.8 . . ?
C27 C26 H26 118.8 . . ?
C26 C27 C28 122.7(2) . . ?
C26 C27 C32 118.9(2) . . ?
C28 C27 C32 118.4(3) . . ?
C29 C28 C27 122.0(3) . . ?
C29 C28 H28 119.0 . . ?
C27 C28 H28 119.0 . . ?
C28 C29 C30 120.1(3) . . ?
C28 C29 H29 119.9 . . ?
C30 C29 H29 119.9 . . ?
C31 C30 C29 120.4(3) . . ?
C31 C30 H30 119.8 . . ?
C29 C30 H30 119.8 . . ?
C30 C31 C32 121.4(2) . . ?
C30 C31 H31 119.3 . . ?
C32 C31 H31 119.3 . . ?
C19 C32 C31 122.90(19) . . ?
C19 C32 C27 119.4(2) . . ?
C31 C32 C27 117.7(2) . . ?
C1 N1 C13 119.87(15) . . ?
C1 N1 C7 120.10(15) . . ?
C13 N1 C7 119.17(15) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        28.28
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.253
_refine_diff_density_min         -0.281
_refine_diff_density_rms         0.095
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichloromethane/methanol'
_chemical_properties_physical    ', Heat-sensitive'
_exptl_crystal_preparation       ', Luminescent'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shen-g
_audit_block_doi                 10.5517/ccdc.csd.cc1p2ywl
_database_code_depnum_ccdc_archive 'CCDC 1551980'
_audit_update_record             
;
2017-05-24 deposited with the CCDC.
2017-08-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        3-(anthracen-9-yl)-N,N-diphenylaniline
_chemical_name_common            ?
_chemical_melting_point          454
_chemical_formula_moiety         'C32 H23 N'
_chemical_formula_sum            'C32 H23 N'
_chemical_formula_weight         421.51

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   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'

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                   14.901(3)
_cell_length_b                   8.3206(17)
_cell_length_c                   18.900(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 101.42(3)
_cell_angle_gamma                90.00
_cell_volume                     2297.0(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    16450
_cell_measurement_theta_min      3.13
_cell_measurement_theta_max      27.51

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.219
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             888
_exptl_absorpt_coefficient_mu    0.070
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9896
_exptl_absorpt_correction_T_max  0.9916
_exptl_absorpt_process_details   ?

_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  'Rigaku RAXIS-RAPID'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            21529
_diffrn_reflns_av_R_equivalents  0.0347
_diffrn_reflns_av_sigmaI/netI    0.0307
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         3.12
_diffrn_reflns_theta_max         27.48
_reflns_number_total             5248
_reflns_number_gt                3650
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'RAPID-AUTO (Rigaku Corporation, 1998)'
_computing_cell_refinement       RAPID-AUTO
_computing_data_reduction        
'CrystalStructure (Rigaku/MSC and Rigaku Corporation, 2002)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  SHELXL-97

_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)+(0.0872P)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         5248
_refine_ls_number_parameters     298
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0661
_refine_ls_R_factor_gt           0.0430
_refine_ls_wR_factor_ref         0.1412
_refine_ls_wR_factor_gt          0.1246
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.034
_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 0.54009(8) 0.06508(15) 0.14948(7) 0.0381(3) Uani 1 1 d . . .
C2 C 0.61141(9) 0.13260(16) 0.19891(8) 0.0466(3) Uani 1 1 d . . .
H2 H 0.6645 0.0736 0.2152 0.056 Uiso 1 1 calc R . .
C3 C 0.60414(11) 0.28693(17) 0.22415(9) 0.0549(4) Uani 1 1 d . . .
H3 H 0.6528 0.3315 0.2567 0.066 Uiso 1 1 calc R . .
C4 C 0.52558(11) 0.37541(17) 0.20168(9) 0.0579(4) Uani 1 1 d . . .
H4 H 0.5205 0.4785 0.2195 0.069 Uiso 1 1 calc R . .
C5 C 0.45501(11) 0.30959(18) 0.15274(10) 0.0594(4) Uani 1 1 d . . .
H5 H 0.4018 0.3688 0.1372 0.071 Uiso 1 1 calc R . .
C6 C 0.46189(10) 0.15621(17) 0.12614(9) 0.0500(4) Uani 1 1 d . . .
H6 H 0.4137 0.1139 0.0924 0.060 Uiso 1 1 calc R . .
C7 C 0.46813(8) -0.18874(15) 0.10019(7) 0.0400(3) Uani 1 1 d . . .
C8 C 0.39808(9) -0.19412(18) 0.13901(9) 0.0511(4) Uani 1 1 d . . .
H8 H 0.4041 -0.1391 0.1825 0.061 Uiso 1 1 calc R . .
C9 C 0.31974(10) -0.2811(2) 0.11297(11) 0.0664(5) Uani 1 1 d . . .
H9 H 0.2724 -0.2819 0.1385 0.080 Uiso 1 1 calc R . .
C10 C 0.31060(11) -0.3666(2) 0.04982(13) 0.0750(6) Uani 1 1 d . . .
H10 H 0.2576 -0.4250 0.0326 0.090 Uiso 1 1 calc R . .
C11 C 0.38085(12) -0.3646(2) 0.01236(11) 0.0719(5) Uani 1 1 d . . .
H11 H 0.3755 -0.4237 -0.0301 0.086 Uiso 1 1 calc R . .
C12 C 0.45897(10) -0.27659(17) 0.03674(8) 0.0525(4) Uani 1 1 d . . .
H12 H 0.5057 -0.2759 0.0107 0.063 Uiso 1 1 calc R . .
C13 C 0.63309(8) -0.14908(14) 0.11069(7) 0.0366(3) Uani 1 1 d . . .
C14 C 0.68774(8) -0.05000(14) 0.07803(7) 0.0381(3) Uani 1 1 d . . .
H14 H 0.6680 0.0536 0.0645 0.046 Uiso 1 1 calc R . .
C15 C 0.77179(8) -0.10344(15) 0.06523(7) 0.0378(3) Uani 1 1 d . . .
C16 C 0.79944(9) -0.26022(15) 0.08419(8) 0.0430(3) Uani 1 1 d . . .
H16 H 0.8549 -0.2981 0.0753 0.052 Uiso 1 1 calc R . .
C17 C 0.74463(9) -0.35963(16) 0.11616(8) 0.0450(3) Uani 1 1 d . . .
H17 H 0.7634 -0.4643 0.1284 0.054 Uiso 1 1 calc R . .
C18 C 0.66225(9) -0.30493(15) 0.13005(7) 0.0424(3) Uani 1 1 d . . .
H18 H 0.6263 -0.3721 0.1523 0.051 Uiso 1 1 calc R . .
C19 C 0.83117(8) 0.00613(15) 0.03208(7) 0.0389(3) Uani 1 1 d . . .
C20 C 0.87702(8) 0.13397(15) 0.07280(7) 0.0402(3) Uani 1 1 d . . .
C21 C 0.86843(10) 0.16685(16) 0.14527(8) 0.0465(3) Uani 1 1 d . . .
H21 H 0.8307 0.1021 0.1669 0.056 Uiso 1 1 calc R . .
C22 C 0.91396(11) 0.29008(17) 0.18319(9) 0.0563(4) Uani 1 1 d . . .
H22 H 0.9064 0.3092 0.2301 0.068 Uiso 1 1 calc R . .
C23 C 0.97258(12) 0.38983(19) 0.15270(10) 0.0633(4) Uani 1 1 d . . .
H23 H 1.0032 0.4743 0.1793 0.076 Uiso 1 1 calc R . .
C24 C 0.98420(11) 0.36235(18) 0.08458(10) 0.0583(4) Uani 1 1 d . . .
H24 H 1.0242 0.4271 0.0652 0.070 Uiso 1 1 calc R . .
C25 C 0.93657(9) 0.23626(16) 0.04170(8) 0.0453(3) Uani 1 1 d . . .
C26 C 0.94590(9) 0.20894(18) -0.02889(9) 0.0519(4) Uani 1 1 d . . .
H26 H 0.9848 0.2747 -0.0488 0.062 Uiso 1 1 calc R . .
C27 C 0.89941(9) 0.08743(18) -0.07057(8) 0.0488(4) Uani 1 1 d . . .
C28 C 0.90665(12) 0.0640(2) -0.14388(10) 0.0669(5) Uani 1 1 d . . .
H28 H 0.9447 0.1308 -0.1643 0.080 Uiso 1 1 calc R . .
C29 C 0.85944(14) -0.0530(3) -0.18412(10) 0.0785(6) Uani 1 1 d . . .
H29 H 0.8650 -0.0658 -0.2320 0.094 Uiso 1 1 calc R . .
C30 C 0.80176(13) -0.1561(2) -0.15444(10) 0.0738(5) Uani 1 1 d . . .
H30 H 0.7693 -0.2360 -0.1831 0.089 Uiso 1 1 calc R . .
C31 C 0.79291(10) -0.1407(2) -0.08463(9) 0.0559(4) Uani 1 1 d . . .
H31 H 0.7551 -0.2111 -0.0658 0.067 Uiso 1 1 calc R . .
C32 C 0.84080(9) -0.01798(16) -0.03981(8) 0.0435(3) Uani 1 1 d . . .
N1 N 0.54775(7) -0.09440(13) 0.12449(6) 0.0430(3) 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 C6 1.3871(18) . ?
C1 C2 1.3873(19) . ?
C1 N1 1.4207(16) . ?
C2 C3 1.3816(19) . ?
C2 H2 0.9300 . ?
C3 C4 1.377(2) . ?
C3 H3 0.9300 . ?
C4 C5 1.370(2) . ?
C4 H4 0.9300 . ?
C5 C6 1.383(2) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C12 1.388(2) . ?
C7 C8 1.3904(18) . ?
C7 N1 1.4209(16) . ?
C8 C9 1.379(2) . ?
C8 H8 0.9300 . ?
C9 C10 1.373(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.375(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.375(2) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 C14 1.3867(17) . ?
C13 C18 1.3933(17) . ?
C13 N1 1.4224(15) . ?
C14 C15 1.3946(16) . ?
C14 H14 0.9300 . ?
C15 C16 1.3934(17) . ?
C15 C19 1.4920(17) . ?
C16 C17 1.3827(19) . ?
C16 H16 0.9300 . ?
C17 C18 1.3822(18) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C19 C20 1.4080(19) . ?
C19 C32 1.4087(18) . ?
C20 C21 1.427(2) . ?
C20 C25 1.4366(18) . ?
C21 C22 1.354(2) . ?
C21 H21 0.9300 . ?
C22 C23 1.408(2) . ?
C22 H22 0.9300 . ?
C23 C24 1.352(2) . ?
C23 H23 0.9300 . ?
C24 C25 1.426(2) . ?
C24 H24 0.9300 . ?
C25 C26 1.387(2) . ?
C26 C27 1.381(2) . ?
C26 H26 0.9300 . ?
C27 C28 1.424(2) . ?
C27 C32 1.4390(19) . ?
C28 C29 1.345(3) . ?
C28 H28 0.9300 . ?
C29 C30 1.408(3) . ?
C29 H29 0.9300 . ?
C30 C31 1.358(2) . ?
C30 H30 0.9300 . ?
C31 C32 1.425(2) . ?
C31 H31 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
C6 C1 C2 118.43(12) . . ?
C6 C1 N1 121.50(12) . . ?
C2 C1 N1 120.06(12) . . ?
C3 C2 C1 120.46(14) . . ?
C3 C2 H2 119.8 . . ?
C1 C2 H2 119.8 . . ?
C4 C3 C2 120.69(15) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C5 C4 C3 119.12(14) . . ?
C5 C4 H4 120.4 . . ?
C3 C4 H4 120.4 . . ?
C4 C5 C6 120.81(15) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C5 C6 C1 120.46(14) . . ?
C5 C6 H6 119.8 . . ?
C1 C6 H6 119.8 . . ?
C12 C7 C8 118.90(13) . . ?
C12 C7 N1 120.22(12) . . ?
C8 C7 N1 120.88(13) . . ?
C9 C8 C7 119.97(16) . . ?
C9 C8 H8 120.0 . . ?
C7 C8 H8 120.0 . . ?
C10 C9 C8 120.90(17) . . ?
C10 C9 H9 119.6 . . ?
C8 C9 H9 119.6 . . ?
C9 C10 C11 119.15(15) . . ?
C9 C10 H10 120.4 . . ?
C11 C10 H10 120.4 . . ?
C10 C11 C12 120.92(18) . . ?
C10 C11 H11 119.5 . . ?
C12 C11 H11 119.5 . . ?
C11 C12 C7 120.13(16) . . ?
C11 C12 H12 119.9 . . ?
C7 C12 H12 119.9 . . ?
C14 C13 C18 119.35(11) . . ?
C14 C13 N1 121.10(11) . . ?
C18 C13 N1 119.55(11) . . ?
C13 C14 C15 120.96(11) . . ?
C13 C14 H14 119.5 . . ?
C15 C14 H14 119.5 . . ?
C16 C15 C14 118.94(11) . . ?
C16 C15 C19 120.68(11) . . ?
C14 C15 C19 120.38(11) . . ?
C17 C16 C15 120.15(11) . . ?
C17 C16 H16 119.9 . . ?
C15 C16 H16 119.9 . . ?
C18 C17 C16 120.64(12) . . ?
C18 C17 H17 119.7 . . ?
C16 C17 H17 119.7 . . ?
C17 C18 C13 119.94(12) . . ?
C17 C18 H18 120.0 . . ?
C13 C18 H18 120.0 . . ?
C20 C19 C32 120.25(12) . . ?
C20 C19 C15 119.74(12) . . ?
C32 C19 C15 120.01(12) . . ?
C19 C20 C21 122.92(12) . . ?
C19 C20 C25 119.74(13) . . ?
C21 C20 C25 117.34(13) . . ?
C22 C21 C20 121.50(14) . . ?
C22 C21 H21 119.3 . . ?
C20 C21 H21 119.3 . . ?
C21 C22 C23 121.08(15) . . ?
C21 C22 H22 119.5 . . ?
C23 C22 H22 119.5 . . ?
C24 C23 C22 119.78(15) . . ?
C24 C23 H23 120.1 . . ?
C22 C23 H23 120.1 . . ?
C23 C24 C25 121.50(14) . . ?
C23 C24 H24 119.3 . . ?
C25 C24 H24 119.3 . . ?
C26 C25 C24 122.26(13) . . ?
C26 C25 C20 118.96(13) . . ?
C24 C25 C20 118.78(14) . . ?
C27 C26 C25 122.29(13) . . ?
C27 C26 H26 118.9 . . ?
C25 C26 H26 118.9 . . ?
C26 C27 C28 121.94(14) . . ?
C26 C27 C32 119.47(13) . . ?
C28 C27 C32 118.59(15) . . ?
C29 C28 C27 121.14(16) . . ?
C29 C28 H28 119.4 . . ?
C27 C28 H28 119.4 . . ?
C28 C29 C30 120.56(17) . . ?
C28 C29 H29 119.7 . . ?
C30 C29 H29 119.7 . . ?
C31 C30 C29 120.94(18) . . ?
C31 C30 H30 119.5 . . ?
C29 C30 H30 119.5 . . ?
C30 C31 C32 120.78(15) . . ?
C30 C31 H31 119.6 . . ?
C32 C31 H31 119.6 . . ?
C19 C32 C31 122.74(13) . . ?
C19 C32 C27 119.25(13) . . ?
C31 C32 C27 117.99(13) . . ?
C1 N1 C7 120.44(10) . . ?
C1 N1 C13 119.56(10) . . ?
C7 N1 C13 118.92(10) . . ?

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 0.1(2) . . . . ?
N1 C1 C2 C3 -179.25(13) . . . . ?
C1 C2 C3 C4 1.1(2) . . . . ?
C2 C3 C4 C5 -1.2(2) . . . . ?
C3 C4 C5 C6 0.2(2) . . . . ?
C4 C5 C6 C1 1.0(2) . . . . ?
C2 C1 C6 C5 -1.1(2) . . . . ?
N1 C1 C6 C5 178.21(13) . . . . ?
C12 C7 C8 C9 -2.3(2) . . . . ?
N1 C7 C8 C9 177.33(13) . . . . ?
C7 C8 C9 C10 1.7(2) . . . . ?
C8 C9 C10 C11 0.0(3) . . . . ?
C9 C10 C11 C12 -1.0(3) . . . . ?
C10 C11 C12 C7 0.4(2) . . . . ?
C8 C7 C12 C11 1.3(2) . . . . ?
N1 C7 C12 C11 -178.37(14) . . . . ?
C18 C13 C14 C15 -0.9(2) . . . . ?
N1 C13 C14 C15 179.35(12) . . . . ?
C13 C14 C15 C16 1.6(2) . . . . ?
C13 C14 C15 C19 -178.13(12) . . . . ?
C14 C15 C16 C17 -1.0(2) . . . . ?
C19 C15 C16 C17 178.75(12) . . . . ?
C15 C16 C17 C18 -0.4(2) . . . . ?
C16 C17 C18 C13 1.1(2) . . . . ?
C14 C13 C18 C17 -0.5(2) . . . . ?
N1 C13 C18 C17 179.31(12) . . . . ?
C16 C15 C19 C20 -107.68(15) . . . . ?
C14 C15 C19 C20 72.02(16) . . . . ?
C16 C15 C19 C32 72.66(17) . . . . ?
C14 C15 C19 C32 -107.63(14) . . . . ?
C32 C19 C20 C21 178.56(12) . . . . ?
C15 C19 C20 C21 -1.09(18) . . . . ?
C32 C19 C20 C25 -2.40(18) . . . . ?
C15 C19 C20 C25 177.95(10) . . . . ?
C19 C20 C21 C22 179.52(13) . . . . ?
C25 C20 C21 C22 0.46(19) . . . . ?
C20 C21 C22 C23 -0.7(2) . . . . ?
C21 C22 C23 C24 -0.3(2) . . . . ?
C22 C23 C24 C25 1.5(2) . . . . ?
C23 C24 C25 C26 178.34(14) . . . . ?
C23 C24 C25 C20 -1.8(2) . . . . ?
C19 C20 C25 C26 1.55(18) . . . . ?
C21 C20 C25 C26 -179.35(12) . . . . ?
C19 C20 C25 C24 -178.35(12) . . . . ?
C21 C20 C25 C24 0.75(18) . . . . ?
C24 C25 C26 C27 -179.63(13) . . . . ?
C20 C25 C26 C27 0.5(2) . . . . ?
C25 C26 C27 C28 177.54(13) . . . . ?
C25 C26 C27 C32 -1.6(2) . . . . ?
C26 C27 C28 C29 -178.66(16) . . . . ?
C32 C27 C28 C29 0.5(2) . . . . ?
C27 C28 C29 C30 -0.3(3) . . . . ?
C28 C29 C30 C31 -0.4(3) . . . . ?
C29 C30 C31 C32 0.9(3) . . . . ?
C20 C19 C32 C31 -177.11(12) . . . . ?
C15 C19 C32 C31 2.55(19) . . . . ?
C20 C19 C32 C27 1.25(18) . . . . ?
C15 C19 C32 C27 -179.09(11) . . . . ?
C30 C31 C32 C19 177.67(15) . . . . ?
C30 C31 C32 C27 -0.7(2) . . . . ?
C26 C27 C32 C19 0.75(19) . . . . ?
C28 C27 C32 C19 -178.44(13) . . . . ?
C26 C27 C32 C31 179.18(12) . . . . ?
C28 C27 C32 C31 0.00(19) . . . . ?
C6 C1 N1 C7 -26.00(19) . . . . ?
C2 C1 N1 C7 153.34(13) . . . . ?
C6 C1 N1 C13 141.96(13) . . . . ?
C2 C1 N1 C13 -38.70(18) . . . . ?
C12 C7 N1 C1 134.66(13) . . . . ?
C8 C7 N1 C1 -44.97(19) . . . . ?
C12 C7 N1 C13 -33.37(18) . . . . ?
C8 C7 N1 C13 147.00(13) . . . . ?
C14 C13 N1 C1 -40.17(18) . . . . ?
C18 C13 N1 C1 140.05(13) . . . . ?
C14 C13 N1 C7 127.96(13) . . . . ?
C18 C13 N1 C7 -51.82(18) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.195
_refine_diff_density_min         -0.190
_refine_diff_density_rms         0.036
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichloromethane/methanol'
_chemical_properties_physical    ', Heat-sensitive'
_exptl_crystal_preparation       ', Luminescent'
