# Electronic Supplementary Material (ESI) for RSC Advances.
# 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_6
_database_code_depnum_ccdc_archive 'CCDC 1477929'
_audit_update_record             
;
2016-05-04 deposited with the CCDC.
2016-07-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C33 H24 N2 O3'
_chemical_formula_sum            'C33 H24 N2 O3'
_chemical_formula_weight         496.54

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

_cell_length_a                   5.616(3)
_cell_length_b                   9.350(4)
_cell_length_c                   25.070(10)
_cell_angle_alpha                88.325(10)
_cell_angle_beta                 87.442(9)
_cell_angle_gamma                83.160(9)
_cell_volume                     1305.3(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1343
_cell_measurement_theta_min      3.01
_cell_measurement_theta_max      26.44

_exptl_crystal_description       Trip
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.263
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             520
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.814
_exptl_absorpt_correction_T_max  0.856
_exptl_absorpt_process_details   SADABS

_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 APEX II CCD area-detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            6737
_diffrn_reflns_av_R_equivalents  0.0445
_diffrn_reflns_av_sigmaI/netI    0.1002
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.19
_diffrn_reflns_theta_max         25.00
_reflns_number_total             4577
_reflns_number_gt                1811
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_cell_refinement       'SAINT-Plus (Bruker, 2001)'
_computing_data_reduction        SAINT-Plus
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'XP (Sheldrick, 1998)'
_computing_publication_material  XP

_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)+(0.0221P)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    noref
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4577
_refine_ls_number_parameters     344
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1721
_refine_ls_R_factor_gt           0.0599
_refine_ls_wR_factor_ref         0.1165
_refine_ls_wR_factor_gt          0.0971
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_restrained_S_all      1.000
_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 0.1214(4) -0.0878(3) 0.39806(9) 0.0615(7) Uani 1 1 d . . .
N2 N 0.1534(7) -0.4956(4) 0.58856(12) 0.0879(10) Uani 1 1 d . . .
O1 O -0.2523(4) -0.0584(3) 0.45813(9) 0.0915(8) Uani 1 1 d . . .
H1 H -0.1593 -0.0434 0.4330 0.137 Uiso 1 1 calc R . .
O2 O 0.0350(5) -0.5413(3) 0.62507(10) 0.1299(11) Uani 1 1 d . . .
O3 O 0.3589(6) -0.5471(3) 0.57812(10) 0.1145(10) Uani 1 1 d . . .
C1 C 0.2119(6) -0.1888(3) 0.42922(12) 0.0687(9) Uani 1 1 d . . .
H1A H 0.3639 -0.2361 0.4212 0.082 Uiso 1 1 calc R . .
C2 C 0.0794(6) -0.2297(3) 0.47674(12) 0.0603(9) Uani 1 1 d . . .
C3 C -0.1507(7) -0.1614(3) 0.48956(13) 0.0657(9) Uani 1 1 d . . .
C4 C -0.2737(6) -0.2028(4) 0.53564(13) 0.0764(10) Uani 1 1 d . . .
H4 H -0.4257 -0.1563 0.5443 0.092 Uiso 1 1 calc R . .
C5 C -0.1751(7) -0.3100(4) 0.56809(12) 0.0738(10) Uani 1 1 d . . .
H5 H -0.2582 -0.3372 0.5989 0.089 Uiso 1 1 calc R . .
C6 C 0.0511(7) -0.3786(4) 0.55477(13) 0.0664(9) Uani 1 1 d . . .
C7 C 0.1772(6) -0.3391(3) 0.50999(12) 0.0677(9) Uani 1 1 d . . .
H7 H 0.3294 -0.3861 0.5019 0.081 Uiso 1 1 calc R . .
C8 C 0.2428(6) -0.0463(3) 0.35022(12) 0.0577(8) Uani 1 1 d . . .
C9 C 0.4704(6) -0.1024(3) 0.33267(12) 0.0675(9) Uani 1 1 d . . .
H9 H 0.5625 -0.1684 0.3540 0.081 Uiso 1 1 calc R . .
C10 C 0.5606(6) -0.0604(3) 0.28359(12) 0.0649(9) Uani 1 1 d . . .
H10 H 0.7125 -0.1009 0.2718 0.078 Uiso 1 1 calc R . .
C11 C 0.4329(6) 0.0400(3) 0.25121(12) 0.0568(8) Uani 1 1 d . . .
C12 C 0.2061(6) 0.0963(3) 0.26946(12) 0.0681(9) Uani 1 1 d . . .
H12 H 0.1151 0.1635 0.2483 0.082 Uiso 1 1 calc R . .
C13 C 0.1130(6) 0.0549(3) 0.31822(13) 0.0698(9) Uani 1 1 d . . .
H13 H -0.0391 0.0952 0.3299 0.084 Uiso 1 1 calc R . .
C14 C 0.5247(5) 0.0766(3) 0.19646(12) 0.0591(9) Uani 1 1 d . . .
C15 C 0.4977(5) 0.2119(3) 0.17496(12) 0.0595(9) Uani 1 1 d . . .
C16 C 0.4186(6) 0.3409(3) 0.20714(13) 0.0613(9) Uani 1 1 d . . .
C17 C 0.5391(6) 0.3711(4) 0.25123(14) 0.0789(10) Uani 1 1 d . . .
H17 H 0.6734 0.3097 0.2611 0.095 Uiso 1 1 calc R . .
C18 C 0.4641(8) 0.4909(5) 0.28115(14) 0.0952(13) Uani 1 1 d . . .
H18 H 0.5470 0.5095 0.3110 0.114 Uiso 1 1 calc R . .
C19 C 0.2677(9) 0.5822(4) 0.26686(16) 0.0925(13) Uani 1 1 d . . .
H19 H 0.2153 0.6624 0.2872 0.111 Uiso 1 1 calc R . .
C20 C 0.1501(7) 0.5554(4) 0.22311(17) 0.0887(12) Uani 1 1 d . . .
H20 H 0.0158 0.6171 0.2134 0.106 Uiso 1 1 calc R . .
C21 C 0.2280(7) 0.4372(4) 0.19288(13) 0.0760(10) Uani 1 1 d . . .
H21 H 0.1492 0.4224 0.1620 0.091 Uiso 1 1 calc R . .
C22 C 0.5377(6) 0.2402(3) 0.11715(13) 0.0603(9) Uani 1 1 d . . .
C23 C 0.4133(7) 0.1764(4) 0.08063(15) 0.0834(11) Uani 1 1 d . . .
H23 H 0.3064 0.1126 0.0925 0.100 Uiso 1 1 calc R . .
C24 C 0.4426(8) 0.2045(4) 0.02684(15) 0.0999(13) Uani 1 1 d . . .
H24 H 0.3546 0.1615 0.0026 0.120 Uiso 1 1 calc R . .
C25 C 0.6028(8) 0.2965(4) 0.00950(15) 0.0958(13) Uani 1 1 d . . .
H25 H 0.6244 0.3152 -0.0269 0.115 Uiso 1 1 calc R . .
C26 C 0.7305(7) 0.3607(4) 0.04430(16) 0.0936(13) Uani 1 1 d . . .
H26 H 0.8404 0.4221 0.0319 0.112 Uiso 1 1 calc R . .
C27 C 0.6959(6) 0.3340(3) 0.09872(14) 0.0783(11) Uani 1 1 d . . .
H27 H 0.7803 0.3798 0.1229 0.094 Uiso 1 1 calc R . .
C28 C 0.6388(6) -0.0469(3) 0.16560(12) 0.0600(9) Uani 1 1 d . . .
C29 C 0.8555(6) -0.0402(4) 0.13776(13) 0.0750(10) Uani 1 1 d . . .
H29 H 0.9342 0.0414 0.1397 0.090 Uiso 1 1 calc R . .
C30 C 0.9547(6) -0.1526(4) 0.10737(13) 0.0815(11) Uani 1 1 d . . .
H30 H 1.0989 -0.1459 0.0883 0.098 Uiso 1 1 calc R . .
C31 C 0.8447(7) -0.2753(4) 0.10464(14) 0.0839(11) Uani 1 1 d . . .
H31 H 0.9127 -0.3514 0.0838 0.101 Uiso 1 1 calc R . .
C32 C 0.6341(7) -0.2838(4) 0.13299(14) 0.0802(11) Uani 1 1 d . . .
H32 H 0.5582 -0.3666 0.1315 0.096 Uiso 1 1 calc R . .
C33 C 0.5327(6) -0.1723(4) 0.16367(12) 0.0699(9) Uani 1 1 d . . .
H33 H 0.3909 -0.1811 0.1834 0.084 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 C1 1.280(3) . ?
N1 C8 1.420(3) . ?
N2 O2 1.206(3) . ?
N2 O3 1.216(3) . ?
N2 C6 1.444(4) . ?
O1 C3 1.319(3) . ?
C1 C2 1.443(4) . ?
C2 C7 1.379(4) . ?
C2 C3 1.399(4) . ?
C3 C4 1.388(4) . ?
C4 C5 1.354(4) . ?
C5 C6 1.384(4) . ?
C6 C7 1.366(3) . ?
C8 C13 1.383(4) . ?
C8 C9 1.381(4) . ?
C9 C10 1.374(3) . ?
C10 C11 1.379(4) . ?
C11 C12 1.382(4) . ?
C11 C14 1.489(4) . ?
C12 C13 1.372(3) . ?
C14 C15 1.355(4) . ?
C14 C28 1.475(4) . ?
C15 C22 1.478(4) . ?
C15 C16 1.483(4) . ?
C16 C21 1.368(4) . ?
C16 C17 1.375(4) . ?
C17 C18 1.380(4) . ?
C18 C19 1.366(5) . ?
C19 C20 1.350(4) . ?
C20 C21 1.375(4) . ?
C22 C23 1.367(4) . ?
C22 C27 1.377(4) . ?
C23 C24 1.373(4) . ?
C24 C25 1.366(4) . ?
C25 C26 1.351(4) . ?
C26 C27 1.389(4) . ?
C28 C29 1.382(4) . ?
C28 C33 1.380(4) . ?
C29 C30 1.366(4) . ?
C30 C31 1.370(4) . ?
C31 C32 1.361(4) . ?
C32 C33 1.367(4) . ?

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
C1 N1 C8 122.3(3) . . ?
O2 N2 O3 122.0(4) . . ?
O2 N2 C6 120.2(4) . . ?
O3 N2 C6 117.8(3) . . ?
N1 C1 C2 120.4(3) . . ?
C7 C2 C3 118.8(3) . . ?
C7 C2 C1 120.1(3) . . ?
C3 C2 C1 121.1(3) . . ?
O1 C3 C4 119.6(3) . . ?
O1 C3 C2 120.6(3) . . ?
C4 C3 C2 119.8(3) . . ?
C5 C4 C3 120.8(3) . . ?
C4 C5 C6 119.1(3) . . ?
C7 C6 C5 121.3(3) . . ?
C7 C6 N2 119.5(3) . . ?
C5 C6 N2 119.1(3) . . ?
C6 C7 C2 120.1(3) . . ?
C13 C8 C9 118.7(3) . . ?
C13 C8 N1 115.6(3) . . ?
C9 C8 N1 125.7(3) . . ?
C10 C9 C8 119.9(3) . . ?
C9 C10 C11 122.0(3) . . ?
C10 C11 C12 117.5(3) . . ?
C10 C11 C14 121.5(3) . . ?
C12 C11 C14 120.7(3) . . ?
C13 C12 C11 121.1(3) . . ?
C12 C13 C8 120.8(3) . . ?
C15 C14 C28 121.5(3) . . ?
C15 C14 C11 123.3(3) . . ?
C28 C14 C11 115.2(3) . . ?
C14 C15 C22 121.9(3) . . ?
C14 C15 C16 122.7(3) . . ?
C22 C15 C16 115.4(3) . . ?
C21 C16 C17 117.4(3) . . ?
C21 C16 C15 121.1(3) . . ?
C17 C16 C15 121.4(3) . . ?
C16 C17 C18 121.1(4) . . ?
C19 C18 C17 119.9(4) . . ?
C20 C19 C18 119.7(4) . . ?
C19 C20 C21 120.2(4) . . ?
C16 C21 C20 121.5(3) . . ?
C23 C22 C27 118.3(3) . . ?
C23 C22 C15 120.6(3) . . ?
C27 C22 C15 121.1(3) . . ?
C22 C23 C24 121.5(3) . . ?
C23 C24 C25 119.0(4) . . ?
C26 C25 C24 121.2(4) . . ?
C25 C26 C27 119.4(3) . . ?
C22 C27 C26 120.5(3) . . ?
C29 C28 C33 118.1(3) . . ?
C29 C28 C14 120.8(3) . . ?
C33 C28 C14 121.0(3) . . ?
C30 C29 C28 120.4(3) . . ?
C31 C30 C29 120.9(3) . . ?
C32 C31 C30 118.9(3) . . ?
C31 C32 C33 121.0(3) . . ?
C32 C33 C28 120.6(3) . . ?

_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         0.190
_refine_diff_density_min         -0.166
_refine_diff_density_rms         0.037
