# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
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# 
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#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_lll

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C29 H19 N3 O2'
_chemical_formula_weight         441.47

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                   7.9933(15)
_cell_length_b                   11.481(2)
_cell_length_c                   12.651(2)
_cell_angle_alpha                86.659(14)
_cell_angle_beta                 72.316(13)
_cell_angle_gamma                86.751(14)
_cell_volume                     1103.3(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    2321
_cell_measurement_theta_min      3.33
_cell_measurement_theta_max      23.11

_exptl_crystal_description       block
_exptl_crystal_colour            YELLOW
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.329
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             460
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.981
_exptl_absorpt_correction_T_max  0.985
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      273(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 'none '
_diffrn_standards_number         none
_diffrn_standards_interval_count none
_diffrn_standards_interval_time  none
_diffrn_standards_decay_%        none
_diffrn_reflns_number            10196
_diffrn_reflns_av_R_equivalents  0.0509
_diffrn_reflns_av_sigmaI/netI    0.0652
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.13
_diffrn_reflns_theta_max         25.50
_reflns_number_total             4083
_reflns_number_gt                2658
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_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)+(0.1128P)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         4083
_refine_ls_number_parameters     307
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0914
_refine_ls_R_factor_gt           0.0574
_refine_ls_wR_factor_ref         0.1823
_refine_ls_wR_factor_gt          0.1517
_refine_ls_goodness_of_fit_ref   0.989
_refine_ls_restrained_S_all      0.989
_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 -0.0907(3) 0.75285(18) 0.41914(17) 0.0434(5) Uani 1 1 d . . .
C2 C -0.1677(3) 0.82677(19) 0.50030(18) 0.0475(6) Uani 1 1 d . . .
H2A H -0.2631 0.8739 0.4941 0.057 Uiso 1 1 calc R . .
C3 C -0.1093(3) 0.83615(18) 0.59584(17) 0.0447(6) Uani 1 1 d . . .
C4 C 0.0273(3) 0.76396(19) 0.60810(17) 0.0426(5) Uani 1 1 d . . .
C5 C 0.1042(3) 0.68010(18) 0.52585(17) 0.0427(5) Uani 1 1 d . . .
C6 C 0.2638(3) 0.54813(18) 0.42529(17) 0.0430(5) Uani 1 1 d . . .
C7 C 0.3855(3) 0.4575(2) 0.38212(18) 0.0504(6) Uani 1 1 d . . .
H7A H 0.4561 0.4231 0.4227 0.061 Uiso 1 1 calc R . .
C8 C 0.3987(3) 0.4202(2) 0.27858(19) 0.0504(6) Uani 1 1 d . . .
H8A H 0.4767 0.3588 0.2490 0.060 Uiso 1 1 calc R . .
C9 C 0.2947(3) 0.47460(19) 0.21809(17) 0.0455(6) Uani 1 1 d . . .
C10 C 0.1705(3) 0.56277(19) 0.25763(17) 0.0448(6) Uani 1 1 d . . .
H10A H 0.1027 0.5977 0.2155 0.054 Uiso 1 1 calc R . .
C11 C 0.1534(3) 0.59589(18) 0.36396(17) 0.0423(5) Uani 1 1 d . . .
C12 C -0.1398(3) 0.74693(18) 0.31510(17) 0.0437(6) Uani 1 1 d . . .
C13 C -0.2369(3) 0.6570(2) 0.2982(2) 0.0568(7) Uani 1 1 d . . .
H13A H -0.2786 0.6002 0.3541 0.068 Uiso 1 1 calc R . .
C14 C -0.2711(4) 0.6525(2) 0.1984(2) 0.0625(7) Uani 1 1 d . . .
H14A H -0.3373 0.5927 0.1876 0.075 Uiso 1 1 calc R . .
C15 C -0.2093(4) 0.7340(2) 0.1152(2) 0.0613(7) Uani 1 1 d . . .
H15A H -0.2309 0.7287 0.0474 0.074 Uiso 1 1 calc R . .
C16 C -0.1153(4) 0.8244(2) 0.1312(2) 0.0628(7) Uani 1 1 d . . .
H16A H -0.0752 0.8813 0.0750 0.075 Uiso 1 1 calc R . .
C17 C -0.0804(3) 0.8304(2) 0.23102(18) 0.0518(6) Uani 1 1 d . . .
H17A H -0.0163 0.8913 0.2417 0.062 Uiso 1 1 calc R . .
C18 C -0.2026(3) 0.92557(19) 0.67802(18) 0.0456(6) Uani 1 1 d . . .
C19 C -0.2576(3) 1.0336(2) 0.6409(2) 0.0535(6) Uani 1 1 d . . .
H19A H -0.2345 1.0501 0.5651 0.064 Uiso 1 1 calc R . .
C20 C -0.3462(4) 1.1166(2) 0.7153(2) 0.0614(7) Uani 1 1 d . . .
H20A H -0.3843 1.1875 0.6893 0.074 Uiso 1 1 calc R . .
C21 C -0.3779(4) 1.0944(2) 0.8275(2) 0.0663(7) Uani 1 1 d . . .
H21A H -0.4346 1.1510 0.8773 0.080 Uiso 1 1 calc R . .
C22 C -0.3253(4) 0.9879(3) 0.8659(2) 0.0651(7) Uani 1 1 d . . .
H22A H -0.3471 0.9724 0.9417 0.078 Uiso 1 1 calc R . .
C23 C -0.2402(3) 0.9043(2) 0.79146(19) 0.0554(6) Uani 1 1 d . . .
H23A H -0.2075 0.8322 0.8182 0.066 Uiso 1 1 calc R . .
C24 C 0.1119(3) 0.77200(19) 0.69759(17) 0.0436(5) Uani 1 1 d . . .
C25 C 0.1993(4) 0.8706(2) 0.7037(2) 0.0580(7) Uani 1 1 d . . .
H25A H 0.2089 0.9309 0.6500 0.070 Uiso 1 1 calc R . .
C26 C 0.2722(4) 0.8810(2) 0.7879(2) 0.0698(8) Uani 1 1 d . . .
H26A H 0.3333 0.9471 0.7896 0.084 Uiso 1 1 calc R . .
C27 C 0.2557(4) 0.7951(3) 0.8688(2) 0.0684(8) Uani 1 1 d . . .
H27A H 0.3010 0.8038 0.9273 0.082 Uiso 1 1 calc R . .
C28 C 0.1713(4) 0.6949(3) 0.8636(2) 0.0633(7) Uani 1 1 d . . .
H28A H 0.1608 0.6357 0.9183 0.076 Uiso 1 1 calc R . .
C29 C 0.1026(3) 0.6827(2) 0.77757(19) 0.0524(6) Uani 1 1 d . . .
H29A H 0.0495 0.6139 0.7731 0.063 Uiso 1 1 calc R . .
N1 N 0.0464(2) 0.67993(15) 0.43183(14) 0.0416(5) Uani 1 1 d . . .
N2 N 0.2335(3) 0.60158(15) 0.52391(15) 0.0476(5) Uani 1 1 d . . .
N3 N 0.3178(3) 0.43753(18) 0.10542(16) 0.0537(5) Uani 1 1 d . . .
O1 O 0.4210(3) 0.35651(18) 0.07084(16) 0.0845(7) Uani 1 1 d . . .
O2 O 0.2309(3) 0.48744(16) 0.05123(14) 0.0789(6) 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 C2 1.346(3) . ?
C1 N1 1.384(3) . ?
C1 C12 1.490(3) . ?
C2 C3 1.433(3) . ?
C3 C4 1.374(3) . ?
C3 C18 1.503(3) . ?
C4 C5 1.431(3) . ?
C4 C24 1.494(3) . ?
C5 N2 1.328(3) . ?
C5 N1 1.401(3) . ?
C6 N2 1.371(3) . ?
C6 C7 1.399(3) . ?
C6 C11 1.412(3) . ?
C7 C8 1.374(3) . ?
C8 C9 1.392(3) . ?
C9 C10 1.380(3) . ?
C9 N3 1.466(3) . ?
C10 C11 1.384(3) . ?
C11 N1 1.399(3) . ?
C12 C17 1.379(3) . ?
C12 C13 1.389(3) . ?
C13 C14 1.375(3) . ?
C14 C15 1.361(4) . ?
C15 C16 1.374(4) . ?
C16 C17 1.380(3) . ?
C18 C23 1.384(3) . ?
C18 C19 1.396(3) . ?
C19 C20 1.385(3) . ?
C20 C21 1.374(4) . ?
C21 C22 1.380(4) . ?
C22 C23 1.384(3) . ?
C24 C25 1.382(3) . ?
C24 C29 1.387(3) . ?
C25 C26 1.374(3) . ?
C26 C27 1.361(4) . ?
C27 C28 1.380(4) . ?
C28 C29 1.377(3) . ?
N3 O1 1.216(3) . ?
N3 O2 1.216(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
C2 C1 N1 117.80(18) . . ?
C2 C1 C12 124.3(2) . . ?
N1 C1 C12 117.89(18) . . ?
C1 C2 C3 123.0(2) . . ?
C4 C3 C2 119.1(2) . . ?
C4 C3 C18 123.40(19) . . ?
C2 C3 C18 117.5(2) . . ?
C3 C4 C5 118.71(18) . . ?
C3 C4 C24 124.56(19) . . ?
C5 C4 C24 116.58(19) . . ?
N2 C5 N1 113.12(18) . . ?
N2 C5 C4 127.83(18) . . ?
N1 C5 C4 118.98(19) . . ?
N2 C6 C7 128.51(19) . . ?
N2 C6 C11 111.86(19) . . ?
C7 C6 C11 119.64(19) . . ?
C8 C7 C6 118.7(2) . . ?
C7 C8 C9 119.8(2) . . ?
C10 C9 C8 123.8(2) . . ?
C10 C9 N3 117.4(2) . . ?
C8 C9 N3 118.7(2) . . ?
C9 C10 C11 115.7(2) . . ?
C10 C11 N1 133.1(2) . . ?
C10 C11 C6 122.2(2) . . ?
N1 C11 C6 104.61(17) . . ?
C17 C12 C13 119.0(2) . . ?
C17 C12 C1 118.9(2) . . ?
C13 C12 C1 122.1(2) . . ?
C14 C13 C12 119.7(2) . . ?
C15 C14 C13 120.9(2) . . ?
C14 C15 C16 120.0(2) . . ?
C15 C16 C17 119.7(2) . . ?
C16 C17 C12 120.7(2) . . ?
C23 C18 C19 117.7(2) . . ?
C23 C18 C3 122.2(2) . . ?
C19 C18 C3 120.04(19) . . ?
C20 C19 C18 121.0(2) . . ?
C21 C20 C19 120.2(2) . . ?
C22 C21 C20 119.8(2) . . ?
C21 C22 C23 119.9(2) . . ?
C22 C23 C18 121.4(2) . . ?
C25 C24 C29 118.2(2) . . ?
C25 C24 C4 120.3(2) . . ?
C29 C24 C4 121.5(2) . . ?
C26 C25 C24 120.9(2) . . ?
C27 C26 C25 120.4(3) . . ?
C26 C27 C28 119.7(2) . . ?
C29 C28 C27 120.1(2) . . ?
C28 C29 C24 120.6(2) . . ?
C1 N1 C11 132.01(17) . . ?
C1 N1 C5 122.24(17) . . ?
C11 N1 C5 105.75(17) . . ?
C5 N2 C6 104.60(17) . . ?
O1 N3 O2 122.7(2) . . ?
O1 N3 C9 118.4(2) . . ?
O2 N3 C9 118.8(2) . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        25.50
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.220
_refine_diff_density_min         -0.287
_refine_diff_density_rms         0.055
_database_code_depnum_ccdc_archive 'CCDC 1012318'
