# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/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_2014110602
_database_code_depnum_ccdc_archive 'CCDC 1056935'
_audit_update_record             
;
2015-06-15 deposited with the CCDC.
2015-08-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ????????
_chemical_melting_point          ?
_chemical_formula_moiety         'C42 H27 N3'
_chemical_formula_sum            'C42 H27 N3'
_chemical_formula_weight         573.67

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)/c
_symmetry_space_group_name_Hall  '-P 2ybc'

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

_cell_length_a                   34.719(7)
_cell_length_b                   7.6271(15)
_cell_length_c                   11.943(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.05(3)
_cell_angle_gamma                90.00
_cell_volume                     3138.5(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.214
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1200
_exptl_absorpt_coefficient_mu    0.071
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9859
_exptl_absorpt_correction_T_max  0.9859
_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            29723
_diffrn_reflns_av_R_equivalents  0.0342
_diffrn_reflns_av_sigmaI/netI    0.0291
_diffrn_reflns_limit_h_min       -44
_diffrn_reflns_limit_h_max       44
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.18
_diffrn_reflns_theta_max         27.47
_reflns_number_total             7134
_reflns_number_gt                5153
_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)+(0.0603P)²+0.3699P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         7134
_refine_ls_number_parameters     514
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0632
_refine_ls_R_factor_gt           0.0443
_refine_ls_wR_factor_ref         0.1263
_refine_ls_wR_factor_gt          0.1150
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.052
_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 0.45551(4) 1.57385(19) 0.37062(13) 0.0513(3) Uani 1 1 d . . .
C2 C 0.25919(3) 0.89852(16) 0.39290(11) 0.0441(3) Uani 1 1 d . . .
C3 C 0.14858(3) 0.65015(16) 0.40410(11) 0.0420(3) Uani 1 1 d . . .
C4 C 0.22178(3) 0.80449(17) 0.40149(11) 0.0444(3) Uani 1 1 d . . .
C5 C 0.10871(3) 0.42555(16) 0.47885(11) 0.0402(3) Uani 1 1 d . . .
C6 C 0.25996(4) 1.02353(18) 0.30699(12) 0.0475(3) Uani 1 1 d . . .
C7 C 0.36070(4) 1.22434(18) 0.38201(12) 0.0471(3) Uani 1 1 d . . .
C8 C 0.29199(4) 0.87178(16) 0.47207(11) 0.0440(3) Uani 1 1 d . . .
C9 C 0.32629(3) 0.97680(17) 0.46674(11) 0.0439(3) Uani 1 1 d . . .
C10 C 0.29383(4) 1.13092(18) 0.30296(12) 0.0489(3) Uani 1 1 d . . .
C11 C 0.32632(4) 1.10576(18) 0.38337(11) 0.0455(3) Uani 1 1 d . . .
C12 C 0.07741(3) 0.67337(16) 0.37458(10) 0.0407(3) Uani 1 1 d . . .
C13 C 0.42284(4) 1.45540(18) 0.37742(11) 0.0476(3) Uani 1 1 d . . .
C14 C 0.47246(4) 1.67924(19) 0.45197(13) 0.0517(3) Uani 1 1 d . . .
C15 C 0.35889(4) 0.9491(2) 0.55027(13) 0.0528(3) Uani 1 1 d . . .
C16 C 0.17843(4) 0.55835(19) 0.36573(14) 0.0526(3) Uani 1 1 d . . .
C17 C 0.29231(4) 0.7499(2) 0.56285(14) 0.0572(4) Uani 1 1 d . . .
C18 C 0.35766(5) 0.8312(2) 0.63399(15) 0.0625(4) Uani 1 1 d . . .
C19 C 0.10189(5) 0.1498(2) 0.62617(15) 0.0637(4) Uani 1 1 d . . .
C20 C 0.38967(4) 1.1890(2) 0.31580(14) 0.0639(4) Uani 1 1 d . . .
C21 C 0.12750(4) 0.4312(2) 0.58800(12) 0.0527(3) Uani 1 1 d . . .
C22 C 0.22792(4) 1.0488(2) 0.22131(14) 0.0631(4) Uani 1 1 d . . .
C23 C 0.04542(4) 0.66102(19) 0.43291(13) 0.0506(3) Uani 1 1 d . . .
C24 C 0.39364(4) 1.4902(2) 0.44371(15) 0.0617(4) Uani 1 1 d . . .
C25 C 0.08304(5) 0.14312(19) 0.51828(15) 0.0568(4) Uani 1 1 d . . .
C26 C 0.08633(4) 0.28037(18) 0.44368(13) 0.0487(3) Uani 1 1 d . . .
C27 C 0.36296(4) 1.3756(2) 0.44566(15) 0.0621(4) Uani 1 1 d . . .
C28 C 0.21476(4) 0.63480(19) 0.36448(14) 0.0546(4) Uani 1 1 d . . .
C29 C 0.42019(4) 1.3048(2) 0.31228(13) 0.0632(4) Uani 1 1 d . . .
C30 C 0.46334(4) 1.6772(2) 0.56577(15) 0.0589(4) Uani 1 1 d . . .
C31 C 0.32378(5) 0.7312(2) 0.64081(16) 0.0675(4) Uani 1 1 d . . .
C32 C 0.19168(4) 0.8939(2) 0.44189(16) 0.0646(4) Uani 1 1 d . . .
C33 C 0.01160(5) 0.8796(2) 0.31469(17) 0.0715(5) Uani 1 1 d . . .
C34 C 0.50422(4) 1.7916(2) 0.43157(14) 0.0617(4) Uani 1 1 d . . .
C35 C 0.07574(5) 0.7896(2) 0.28449(12) 0.0580(4) Uani 1 1 d . . .
C36 C 0.29318(5) 1.2576(2) 0.21523(15) 0.0685(5) Uani 1 1 d . . .
C37 C 0.22895(5) 1.1687(3) 0.13861(18) 0.0825(6) Uani 1 1 d . . .
C38 C 0.12397(5) 0.2933(2) 0.66109(15) 0.0667(4) Uani 1 1 d . . .
C39 C 0.15557(4) 0.8183(2) 0.44383(16) 0.0622(4) Uani 1 1 d . . .
C40 C 0.01290(4) 0.7637(2) 0.40238(17) 0.0658(4) Uani 1 1 d . . .
C41 C 0.04331(6) 0.8923(2) 0.25608(15) 0.0719(5) Uani 1 1 d . . .
C42 C 0.26204(6) 1.2754(3) 0.13615(19) 0.0895(7) Uani 1 1 d . . .
H1 H 0.2694(5) 0.683(2) 0.5640(13) 0.061(4) Uiso 1 1 d . . .
H2 H 0.3819(4) 1.017(2) 0.5461(12) 0.056(4) Uiso 1 1 d . . .
H3 H 0.0460(5) 0.581(2) 0.4940(14) 0.064(5) Uiso 1 1 d . . .
H4 H 0.3796(5) 0.815(2) 0.6958(15) 0.073(5) Uiso 1 1 d . . .
H5 H 0.2051(5) 0.976(2) 0.2240(14) 0.069(5) Uiso 1 1 d . . .
H6 H 0.1732(5) 0.440(2) 0.3397(13) 0.065(4) Uiso 1 1 d . . .
H7 H 0.0680(5) 0.046(2) 0.4939(14) 0.069(5) Uiso 1 1 d . . .
H8 H 0.1430(5) 0.540(2) 0.6117(14) 0.073(5) Uiso 1 1 d . . .
H9 H 0.0988(5) 0.795(2) 0.2427(15) 0.070(5) Uiso 1 1 d . . .
H10 H 0.2351(5) 0.569(2) 0.3318(14) 0.068(5) Uiso 1 1 d . . .
H11 H 0.3228(5) 0.654(3) 0.7031(16) 0.080(5) Uiso 1 1 d . . .
H12 H 0.3415(5) 1.403(2) 0.4887(15) 0.074(5) Uiso 1 1 d . . .
H13 H 0.4401(5) 1.284(2) 0.2606(16) 0.085(6) Uiso 1 1 d . . .
H14 H 0.1355(5) 0.884(2) 0.4755(15) 0.077(5) Uiso 1 1 d . . .
H15 H 0.3157(5) 1.334(3) 0.2133(15) 0.082(5) Uiso 1 1 d . . .
H16 H 0.3938(5) 1.597(2) 0.4904(15) 0.076(5) Uiso 1 1 d . . .
H17 H 0.1959(6) 1.012(3) 0.4684(16) 0.089(6) Uiso 1 1 d . . .
H18 H -0.0098(6) 0.955(3) 0.2949(16) 0.085(6) Uiso 1 1 d . . .
H19 H 0.3885(5) 1.083(3) 0.2680(16) 0.082(5) Uiso 1 1 d . . .
H20 H 0.2634(6) 1.356(3) 0.080(2) 0.106(7) Uiso 1 1 d . . .
H21 H 0.0728(5) 0.282(2) 0.3678(15) 0.066(5) Uiso 1 1 d . . .
H22 H 0.4670(5) 1.573(2) 0.2991(14) 0.064(4) Uiso 1 1 d . . .
H23 H 0.0989(5) 0.056(3) 0.6753(16) 0.081(5) Uiso 1 1 d . . .
H24 H -0.0092(6) 0.751(3) 0.4463(16) 0.089(6) Uiso 1 1 d . . .
H25 H 0.0438(6) 0.974(3) 0.1963(18) 0.092(6) Uiso 1 1 d . . .
H26 H 0.1375(6) 0.300(3) 0.7402(18) 0.088(6) Uiso 1 1 d . . .
H27 H 0.2067(6) 1.184(3) 0.0790(18) 0.096(6) Uiso 1 1 d . . .
N1 N 0.11111(3) 0.56969(14) 0.40350(9) 0.0436(3) Uani 1 1 d . . .
N2 N 0.52961(5) 1.8790(2) 0.41609(15) 0.0866(5) Uani 1 1 d . . .
N3 N 0.45738(5) 1.6685(2) 0.65753(14) 0.0849(5) 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 C14 1.340(2) . ?
C1 C13 1.4603(18) . ?
C2 C8 1.4028(19) . ?
C2 C6 1.4033(19) . ?
C2 C4 1.4981(16) . ?
C3 C16 1.3752(19) . ?
C3 C39 1.3786(19) . ?
C3 N1 1.4374(15) . ?
C4 C28 1.3797(19) . ?
C4 C32 1.383(2) . ?
C5 C21 1.385(2) . ?
C5 C26 1.3877(18) . ?
C5 N1 1.4296(16) . ?
C6 C22 1.429(2) . ?
C6 C10 1.4388(17) . ?
C7 C27 1.378(2) . ?
C7 C20 1.380(2) . ?
C7 C11 1.4992(17) . ?
C8 C17 1.427(2) . ?
C8 C9 1.4431(17) . ?
C9 C11 1.3997(19) . ?
C9 C15 1.430(2) . ?
C10 C11 1.402(2) . ?
C10 C36 1.423(2) . ?
C12 C23 1.3846(19) . ?
C12 C35 1.3900(19) . ?
C12 N1 1.4195(16) . ?
C13 C29 1.384(2) . ?
C13 C24 1.386(2) . ?
C14 C30 1.433(2) . ?
C14 C34 1.4410(19) . ?
C15 C18 1.349(2) . ?
C16 C28 1.3914(19) . ?
C17 C31 1.353(2) . ?
C18 C31 1.413(2) . ?
C19 C38 1.372(3) . ?
C19 C25 1.373(2) . ?
C20 C29 1.384(2) . ?
C21 C38 1.381(2) . ?
C22 C37 1.350(2) . ?
C23 C40 1.386(2) . ?
C24 C27 1.381(2) . ?
C25 C26 1.388(2) . ?
C30 N3 1.142(2) . ?
C32 C39 1.383(2) . ?
C33 C40 1.367(3) . ?
C33 C41 1.379(3) . ?
C34 N2 1.1379(19) . ?
C35 C41 1.379(2) . ?
C36 C42 1.352(3) . ?
C37 C42 1.411(3) . ?

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 C1 C13 127.28(14) . . ?
C8 C2 C6 120.32(11) . . ?
C8 C2 C4 121.54(12) . . ?
C6 C2 C4 118.02(12) . . ?
C16 C3 C39 118.69(12) . . ?
C16 C3 N1 119.97(11) . . ?
C39 C3 N1 121.33(12) . . ?
C28 C4 C32 117.57(12) . . ?
C28 C4 C2 123.20(11) . . ?
C32 C4 C2 119.10(12) . . ?
C21 C5 C26 119.41(13) . . ?
C21 C5 N1 120.76(12) . . ?
C26 C5 N1 119.80(12) . . ?
C2 C6 C22 122.15(12) . . ?
C2 C6 C10 120.02(12) . . ?
C22 C6 C10 117.84(13) . . ?
C27 C7 C20 118.90(12) . . ?
C27 C7 C11 119.36(12) . . ?
C20 C7 C11 121.70(12) . . ?
C2 C8 C17 122.46(12) . . ?
C2 C8 C9 119.71(12) . . ?
C17 C8 C9 117.74(13) . . ?
C11 C9 C15 122.03(12) . . ?
C11 C9 C8 119.61(12) . . ?
C15 C9 C8 118.31(13) . . ?
C11 C10 C36 122.40(12) . . ?
C11 C10 C6 119.44(12) . . ?
C36 C10 C6 118.16(13) . . ?
C9 C11 C10 120.84(11) . . ?
C9 C11 C7 120.11(12) . . ?
C10 C11 C7 119.00(12) . . ?
C23 C12 C35 118.23(13) . . ?
C23 C12 N1 121.86(12) . . ?
C35 C12 N1 119.90(12) . . ?
C29 C13 C24 118.52(12) . . ?
C29 C13 C1 118.72(13) . . ?
C24 C13 C1 122.73(13) . . ?
C1 C14 C30 123.54(13) . . ?
C1 C14 C34 120.75(14) . . ?
C30 C14 C34 115.45(13) . . ?
C18 C15 C9 121.40(14) . . ?
C3 C16 C28 120.77(13) . . ?
C31 C17 C8 121.44(14) . . ?
C15 C18 C31 120.32(16) . . ?
C38 C19 C25 119.95(15) . . ?
C7 C20 C29 120.48(14) . . ?
C38 C21 C5 120.21(15) . . ?
C37 C22 C6 121.80(14) . . ?
C12 C23 C40 120.48(14) . . ?
C27 C24 C13 120.52(14) . . ?
C19 C25 C26 120.47(15) . . ?
C5 C26 C25 119.64(14) . . ?
C7 C27 C24 120.84(14) . . ?
C4 C28 C16 120.95(13) . . ?
C13 C29 C20 120.71(13) . . ?
N3 C30 C14 176.47(19) . . ?
C17 C31 C18 120.75(16) . . ?
C39 C32 C4 121.71(14) . . ?
C40 C33 C41 118.76(15) . . ?
N2 C34 C14 179.2(2) . . ?
C41 C35 C12 120.52(15) . . ?
C42 C36 C10 121.43(15) . . ?
C22 C37 C42 120.06(17) . . ?
C19 C38 C21 120.32(16) . . ?
C3 C39 C32 120.27(13) . . ?
C33 C40 C23 121.07(16) . . ?
C33 C41 C35 120.93(16) . . ?
C36 C42 C37 120.71(17) . . ?
C12 N1 C5 118.12(9) . . ?
C12 N1 C3 118.81(10) . . ?
C5 N1 C3 116.62(10) . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        27.47
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.149
_refine_diff_density_min         -0.211
_refine_diff_density_rms         0.036
_chemical_properties_physical    Photo-sensitive
_exptl_crystal_preparation       Luminescent
