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

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#                                CCDC 
# 
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# 
#  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.
#
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#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
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#  except for the purpose of generating routine backup copies
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#  data retrieval see:
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data_pb1

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C48 H48 N8 O4'
_chemical_formula_sum            'C48 H48 N8 O4'
_chemical_formula_weight         800.94

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           Trigonal
_symmetry_space_group_name_H-M   R-3

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'

_cell_length_a                   32.703(2)
_cell_length_b                   32.703(2)
_cell_length_c                   20.7189(14)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_volume                     19190(2)
_cell_formula_units_Z            18
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      2.4
_cell_measurement_theta_max      28.4

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.30
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.248
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             7632
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.666
_exptl_absorpt_correction_T_max  0.7445
_exptl_absorpt_process_details   sadabs

_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  ?
_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            139193
_diffrn_reflns_av_R_equivalents  0.0529
_diffrn_reflns_av_sigmaI/netI    0.0246
_diffrn_reflns_limit_h_min       -43
_diffrn_reflns_limit_h_max       43
_diffrn_reflns_limit_k_min       -43
_diffrn_reflns_limit_k_max       43
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         2.44
_diffrn_reflns_theta_max         28.38
_reflns_number_total             10651
_reflns_number_gt                8959
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker, 2010)'
_computing_cell_refinement       'APEX2 (Bruker, 2010); SAINT (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009);XPREP(Sheldrick,2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_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)+(0.2000P)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    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         10651
_refine_ls_number_parameters     573
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0685
_refine_ls_R_factor_gt           0.0542
_refine_ls_wR_factor_ref         0.2133
_refine_ls_wR_factor_gt          0.1955
_refine_ls_goodness_of_fit_ref   0.898
_refine_ls_restrained_S_all      0.898
_refine_ls_shift/su_max          0.001
_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
O4 O 0.58218(4) -0.13958(4) 0.75010(5) 0.0222(2) Uani 1 1 d . . .
O3 O 0.58799(4) -0.02690(4) 0.55642(5) 0.0249(3) Uani 1 1 d . . .
O1 O 0.39170(4) -0.24974(4) 1.04593(6) 0.0300(3) Uani 1 1 d . . .
O2 O 0.55884(4) -0.12948(4) 0.93899(6) 0.0294(3) Uani 1 1 d . . .
N1 N 0.49833(4) -0.18630(5) 1.06316(6) 0.0217(3) Uani 1 1 d . . .
N6 N 0.61577(5) -0.09893(5) 0.61420(6) 0.0210(3) Uani 1 1 d . . .
N3 N 0.42049(5) -0.29806(5) 1.01675(7) 0.0248(3) Uani 1 1 d . . .
N5 N 0.52958(5) -0.10773(4) 0.65077(6) 0.0199(3) Uani 1 1 d . . .
N8 N 0.64641(5) -0.06799(4) 0.77524(6) 0.0193(3) Uani 1 1 d . . .
N2 N 0.45837(4) -0.15281(4) 0.97454(6) 0.0214(3) Uani 1 1 d . . .
N7 N 0.59171(5) 0.01518(5) 0.64639(6) 0.0219(3) Uani 1 1 d . . .
N4 N 0.51537(5) -0.17330(5) 0.85298(7) 0.0250(3) Uani 1 1 d . . .
C9A C 0.57201(5) -0.06382(5) 0.66554(6) 0.0159(3) Uani 1 1 d . . .
C17A C 0.61531(5) -0.07306(5) 0.67090(6) 0.0166(3) Uani 1 1 d . . .
C23A C 0.67600(5) -0.02473(5) 0.74447(7) 0.0184(3) Uani 1 1 d . . .
C15A C 0.58350(5) 0.00726(5) 0.71284(7) 0.0202(3) Uani 1 1 d . . .
C11A C 0.55573(5) -0.05635(5) 0.78846(7) 0.0206(3) Uani 1 1 d . . .
H11A H 0.5444 -0.0880 0.7980 0.025 Uiso 1 1 calc R . .
C9 C 0.47440(5) -0.21621(5) 1.00769(7) 0.0197(3) Uani 1 1 d . . .
C4 C 0.48046(6) -0.15495(6) 1.08401(8) 0.0257(3) Uani 1 1 d . . .
C10 C 0.49705(5) -0.24571(5) 0.98921(7) 0.0212(3) Uani 1 1 d . . .
C18A C 0.66092(5) -0.02676(5) 0.68100(7) 0.0188(3) Uani 1 1 d . . .
C16 C 0.42328(5) -0.25578(5) 1.02520(8) 0.0226(3) Uani 1 1 d . . .
C17 C 0.47262(5) -0.18559(5) 0.95043(7) 0.0189(3) Uani 1 1 d . . .
C16A C 0.58486(5) -0.02385(5) 0.61485(7) 0.0179(3) Uani 1 1 d . . .
C15 C 0.46363(5) -0.29326(5) 0.99610(8) 0.0227(3) Uani 1 1 d . . .
C10A C 0.56866(5) -0.03976(5) 0.72653(7) 0.0171(3) Uani 1 1 d . . .
C22A C 0.71432(6) 0.01430(6) 0.77042(7) 0.0239(3) Uani 1 1 d . . .
H22A H 0.7231 0.0151 0.8133 0.029 Uiso 1 1 calc R . .
C18 C 0.44068(5) -0.21417(5) 0.89431(8) 0.0216(3) Uani 1 1 d . . .
C14A C 0.58797(6) 0.03925(6) 0.75965(9) 0.0269(3) Uani 1 1 d . . .
H14A H 0.5982 0.0706 0.7497 0.032 Uiso 1 1 calc R . .
C5 C 0.48633(6) -0.12280(6) 1.02861(8) 0.0255(3) Uani 1 1 d . . .
C21A C 0.73930(6) 0.05264(6) 0.72944(8) 0.0285(4) Uani 1 1 d . . .
H21A H 0.7649 0.0800 0.7455 0.034 Uiso 1 1 calc R . .
C23 C 0.46754(6) -0.20372(6) 0.83836(8) 0.0241(3) Uani 1 1 d . . .
C24A C 0.61137(5) -0.09855(5) 0.73642(7) 0.0177(3) Uani 1 1 d . . .
C19 C 0.39199(6) -0.24132(6) 0.88991(8) 0.0263(3) Uani 1 1 d . . .
H19 H 0.3734 -0.2486 0.9267 0.032 Uiso 1 1 calc R . .
C11 C 0.54280(6) -0.23300(6) 0.97222(9) 0.0274(3) Uani 1 1 d . . .
H11 H 0.5658 -0.2014 0.9681 0.033 Uiso 1 1 calc R . .
C13A C 0.57637(6) 0.02230(6) 0.82249(8) 0.0302(4) Uani 1 1 d . . .
H13A H 0.5798 0.0430 0.8555 0.036 Uiso 1 1 calc R . .
C19A C 0.68732(5) 0.01104(6) 0.64010(7) 0.0241(3) Uani 1 1 d . . .
H19A H 0.6789 0.0099 0.5970 0.029 Uiso 1 1 calc R . .
C5A C 0.57132(6) -0.14341(6) 0.60186(7) 0.0247(3) Uani 1 1 d . . .
C8 C 0.45484(6) -0.12164(6) 0.92667(9) 0.0297(4) Uani 1 1 d . . .
H8A H 0.4257 -0.1383 0.9023 0.036 Uiso 1 1 calc R . .
H8B H 0.4813 -0.1092 0.8969 0.036 Uiso 1 1 calc R . .
C1 C 0.50033(6) -0.21063(7) 1.12191(8) 0.0316(4) Uani 1 1 d . . .
H1A H 0.5255 -0.2181 1.1190 0.038 Uiso 1 1 calc R . .
H1B H 0.4706 -0.2396 1.1289 0.038 Uiso 1 1 calc R . .
C20 C 0.37131(6) -0.25764(6) 0.82981(9) 0.0313(4) Uani 1 1 d . . .
H20 H 0.3387 -0.2763 0.8266 0.038 Uiso 1 1 calc R . .
C14 C 0.47385(6) -0.32898(6) 0.98560(9) 0.0285(4) Uani 1 1 d . . .
H14 H 0.4510 -0.3606 0.9904 0.034 Uiso 1 1 calc R . .
C12A C 0.55990(6) -0.02462(6) 0.83688(7) 0.0263(3) Uani 1 1 d . . .
H12A H 0.5515 -0.0352 0.8791 0.032 Uiso 1 1 calc R . .
C8A C 0.65299(7) -0.11144(7) 0.61229(8) 0.0318(4) Uani 1 1 d . . .
H8A1 H 0.6545 -0.1258 0.6525 0.038 Uiso 1 1 calc R . .
H8A2 H 0.6836 -0.0840 0.6036 0.038 Uiso 1 1 calc R . .
C22 C 0.44760(7) -0.21904(7) 0.77789(8) 0.0312(4) Uani 1 1 d . . .
H22 H 0.4662 -0.2113 0.7410 0.037 Uiso 1 1 calc R . .
C12 C 0.55380(6) -0.26839(6) 0.96133(9) 0.0329(4) Uani 1 1 d . . .
H12 H 0.5844 -0.2603 0.9497 0.039 Uiso 1 1 calc R . .
C1A C 0.48650(6) -0.10514(6) 0.64304(9) 0.0301(4) Uani 1 1 d . . .
H1A1 H 0.4919 -0.0790 0.6153 0.036 Uiso 1 1 calc R . .
H1A2 H 0.4748 -0.1015 0.6845 0.036 Uiso 1 1 calc R . .
C21 C 0.39890(7) -0.24632(7) 0.77435(9) 0.0355(4) Uani 1 1 d . . .
H21 H 0.3845 -0.2572 0.7345 0.043 Uiso 1 1 calc R . .
C4A C 0.53253(6) -0.13221(6) 0.59237(7) 0.0233(3) Uani 1 1 d . . .
C3 C 0.50959(7) -0.13311(8) 1.14442(9) 0.0365(4) Uani 1 1 d . . .
H3A H 0.4949 -0.1203 1.1722 0.044 Uiso 1 1 calc R . .
H3B H 0.5413 -0.1083 1.1337 0.044 Uiso 1 1 calc R . .
C6 C 0.46526(7) -0.09083(7) 1.03650(10) 0.0373(4) Uani 1 1 d . . .
H6A H 0.4873 -0.0615 1.0577 0.045 Uiso 1 1 calc R . .
H6B H 0.4363 -0.1063 1.0614 0.045 Uiso 1 1 calc R . .
C6A C 0.58500(7) -0.16284(6) 0.54419(8) 0.0335(4) Uani 1 1 d . . .
H6A1 H 0.5812 -0.1498 0.5041 0.040 Uiso 1 1 calc R . .
H6A2 H 0.5660 -0.1970 0.5424 0.040 Uiso 1 1 calc R . .
C20A C 0.72673(6) 0.05080(6) 0.66505(8) 0.0292(4) Uani 1 1 d . . .
H20A H 0.7448 0.0764 0.6382 0.035 Uiso 1 1 calc R . .
C7 C 0.45568(7) -0.08185(6) 0.96715(11) 0.0371(4) Uani 1 1 d . . .
H7A H 0.4804 -0.0513 0.9522 0.044 Uiso 1 1 calc R . .
H7B H 0.4256 -0.0828 0.9643 0.044 Uiso 1 1 calc R . .
C13 C 0.51984(7) -0.31538(6) 0.96755(9) 0.0328(4) Uani 1 1 d . . .
H13 H 0.5279 -0.3384 0.9595 0.039 Uiso 1 1 calc R . .
C24 C 0.52151(5) -0.15923(5) 0.91525(8) 0.0218(3) Uani 1 1 d . . .
C3A C 0.48194(7) -0.17333(7) 0.58868(9) 0.0371(4) Uani 1 1 d . . .
H3A1 H 0.4777 -0.1991 0.6164 0.045 Uiso 1 1 calc R . .
H3A2 H 0.4738 -0.1849 0.5448 0.045 Uiso 1 1 calc R . .
C2 C 0.51001(7) -0.17503(8) 1.17609(9) 0.0410(5) Uani 1 1 d . . .
H2A H 0.5404 -0.1651 1.1959 0.049 Uiso 1 1 calc R . .
H2B H 0.4858 -0.1889 1.2091 0.049 Uiso 1 1 calc R . .
C7A C 0.63708(8) -0.14706(8) 0.55628(9) 0.0419(5) Uani 1 1 d . . .
H7A1 H 0.6557 -0.1323 0.5180 0.050 Uiso 1 1 calc R . .
H7A2 H 0.6406 -0.1739 0.5678 0.050 Uiso 1 1 calc R . .
C2A C 0.45181(7) -0.15261(7) 0.61179(10) 0.0418(5) Uani 1 1 d . . .
H2A1 H 0.4285 -0.1734 0.6429 0.050 Uiso 1 1 calc R . .
H2A2 H 0.4356 -0.1480 0.5758 0.050 Uiso 1 1 calc R . .
H4A H 0.5406(7) -0.1119(7) 0.5536(10) 0.031(5) Uiso 1 1 d . . .
H5 H 0.5209(7) -0.1028(7) 1.0176(9) 0.024(5) Uiso 1 1 d . . .
H5A H 0.5643(7) -0.1655(7) 0.6399(9) 0.021(4) Uiso 1 1 d . . .
H4 H 0.4462(7) -0.1734(7) 1.0967(9) 0.026(5) Uiso 1 1 d . . .
H4B H 0.5389(7) -0.1626(7) 0.8231(10) 0.032(5) Uiso 1 1 d . . .
H8 H 0.6530(8) -0.0736(8) 0.8149(11) 0.041(6) Uiso 1 1 d . . .
H7 H 0.6012(9) 0.0430(9) 0.6243(12) 0.052(7) Uiso 1 1 d . . .
H3 H 0.3953(9) -0.3274(9) 1.0277(11) 0.044(6) Uiso 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
O4 C24A 1.2294(18) . ?
O3 C16A 1.2231(17) . ?
O1 C16 1.2222(19) . ?
O2 C24 1.2212(19) . ?
N1 C9 1.4575(19) . ?
N1 C4 1.476(2) . ?
N1 C1 1.474(2) . ?
N6 C17A 1.4522(18) . ?
N6 C8A 1.466(2) . ?
N6 C5A 1.476(2) . ?
N3 C16 1.351(2) . ?
N3 C15 1.406(2) . ?
N5 C9A 1.4451(18) . ?
N5 C1A 1.462(2) . ?
N5 C4A 1.4803(19) . ?
N8 C24A 1.3466(19) . ?
N8 C23A 1.4054(19) . ?
N2 C17 1.4543(19) . ?
N2 C5 1.469(2) . ?
N2 C8 1.468(2) . ?
N7 C16A 1.349(2) . ?
N7 C15A 1.4019(19) . ?
N4 C24 1.350(2) . ?
N4 C23 1.404(2) . ?
C9A C10A 1.5213(19) . ?
C9A C16A 1.5618(19) . ?
C9A C17A 1.593(2) . ?
C17A C18A 1.517(2) . ?
C17A C24A 1.5643(18) . ?
C23A C22A 1.374(2) . ?
C23A C18A 1.3943(19) . ?
C15A C14A 1.380(2) . ?
C15A C10A 1.391(2) . ?
C11A C10A 1.3748(19) . ?
C11A C12A 1.400(2) . ?
C9 C10 1.530(2) . ?
C9 C16 1.561(2) . ?
C9 C17 1.572(2) . ?
C4 C5 1.503(2) . ?
C4 C3 1.518(2) . ?
C10 C11 1.383(2) . ?
C10 C15 1.391(2) . ?
C18A C19A 1.387(2) . ?
C17 C18 1.530(2) . ?
C17 C24 1.566(2) . ?
C15 C14 1.384(2) . ?
C22A C21A 1.391(2) . ?
C18 C19 1.385(2) . ?
C18 C23 1.390(2) . ?
C14A C13A 1.391(2) . ?
C5 C6 1.521(2) . ?
C21A C20A 1.389(2) . ?
C23 C22 1.385(2) . ?
C19 C20 1.390(2) . ?
C11 C12 1.391(2) . ?
C13A C12A 1.381(2) . ?
C19A C20A 1.394(2) . ?
C5A C4A 1.499(2) . ?
C5A C6A 1.522(2) . ?
C8 C7 1.537(3) . ?
C1 C2 1.532(3) . ?
C20 C21 1.392(3) . ?
C14 C13 1.390(3) . ?
C8A C7A 1.539(3) . ?
C22 C21 1.385(3) . ?
C12 C13 1.380(3) . ?
C1A C2A 1.535(3) . ?
C4A C3A 1.525(2) . ?
C3 C2 1.526(3) . ?
C6 C7 1.530(3) . ?
C6A C7A 1.533(3) . ?
C3A C2A 1.525(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
C9 N1 C4 115.51(12) . . ?
C9 N1 C1 116.29(13) . . ?
C4 N1 C1 105.85(13) . . ?
C17A N6 C8A 115.87(12) . . ?
C17A N6 C5A 114.98(12) . . ?
C8A N6 C5A 105.45(13) . . ?
C16 N3 C15 112.02(13) . . ?
C9A N5 C1A 116.09(12) . . ?
C9A N5 C4A 114.88(12) . . ?
C1A N5 C4A 105.48(12) . . ?
C24A N8 C23A 112.23(12) . . ?
C17 N2 C5 115.64(12) . . ?
C17 N2 C8 116.45(13) . . ?
C5 N2 C8 106.87(13) . . ?
C16A N7 C15A 112.02(12) . . ?
C24 N4 C23 111.76(13) . . ?
N5 C9A C10A 114.09(11) . . ?
N5 C9A C16A 114.35(11) . . ?
C10A C9A C16A 100.63(11) . . ?
N5 C9A C17A 109.23(11) . . ?
C10A C9A C17A 109.93(11) . . ?
C16A C9A C17A 108.24(11) . . ?
N6 C17A C18A 113.68(12) . . ?
N6 C17A C24A 114.43(12) . . ?
C18A C17A C24A 100.95(11) . . ?
N6 C17A C9A 108.85(11) . . ?
C18A C17A C9A 110.13(11) . . ?
C24A C17A C9A 108.51(11) . . ?
C22A C23A C18A 123.34(14) . . ?
C22A C23A N8 127.34(13) . . ?
C18A C23A N8 109.31(13) . . ?
C14A C15A C10A 122.77(14) . . ?
C14A C15A N7 127.75(14) . . ?
C10A C15A N7 109.48(13) . . ?
C10A C11A C12A 118.65(14) . . ?
N1 C9 C10 110.71(12) . . ?
N1 C9 C16 111.48(12) . . ?
C10 C9 C16 101.00(12) . . ?
N1 C9 C17 110.25(12) . . ?
C10 C9 C17 113.35(12) . . ?
C16 C9 C17 109.76(11) . . ?
N1 C4 C5 107.81(13) . . ?
N1 C4 C3 101.24(13) . . ?
C5 C4 C3 118.03(15) . . ?
C11 C10 C15 119.29(14) . . ?
C11 C10 C9 131.79(14) . . ?
C15 C10 C9 108.77(13) . . ?
C19A C18A C23A 119.08(14) . . ?
C19A C18A C17A 131.92(13) . . ?
C23A C18A C17A 108.99(12) . . ?
O1 C16 N3 125.52(14) . . ?
O1 C16 C9 126.07(14) . . ?
N3 C16 C9 108.33(13) . . ?
N2 C17 C18 109.81(12) . . ?
N2 C17 C24 111.68(12) . . ?
C18 C17 C24 100.36(12) . . ?
N2 C17 C9 109.73(12) . . ?
C18 C17 C9 114.57(12) . . ?
C24 C17 C9 110.43(11) . . ?
O3 C16A N7 125.13(14) . . ?
O3 C16A C9A 126.56(14) . . ?
N7 C16A C9A 108.30(12) . . ?
C14 C15 C10 122.79(15) . . ?
C14 C15 N3 127.31(15) . . ?
C10 C15 N3 109.86(14) . . ?
C11A C10A C15A 119.68(14) . . ?
C11A C10A C9A 131.20(13) . . ?
C15A C10A C9A 109.08(12) . . ?
C23A C22A C21A 116.75(14) . . ?
C19 C18 C23 119.04(15) . . ?
C19 C18 C17 131.04(15) . . ?
C23 C18 C17 109.22(13) . . ?
C15A C14A C13A 116.82(15) . . ?
N2 C5 C4 107.22(13) . . ?
N2 C5 C6 101.35(13) . . ?
C4 C5 C6 117.09(15) . . ?
C20A C21A C22A 121.30(16) . . ?
C22 C23 C18 122.68(16) . . ?
C22 C23 N4 127.41(16) . . ?
C18 C23 N4 109.72(14) . . ?
O4 C24A N8 125.49(13) . . ?
O4 C24A C17A 126.43(13) . . ?
N8 C24A C17A 108.06(12) . . ?
C18 C19 C20 119.20(16) . . ?
C10 C11 C12 118.82(15) . . ?
C12A C13A C14A 121.46(15) . . ?
C18A C19A C20A 118.55(14) . . ?
N6 C5A C4A 108.58(12) . . ?
N6 C5A C6A 101.37(14) . . ?
C4A C5A C6A 117.42(13) . . ?
N2 C8 C7 104.18(15) . . ?
N1 C1 C2 104.06(15) . . ?
C21 C20 C19 120.74(16) . . ?
C15 C14 C13 116.86(15) . . ?
C13A C12A C11A 120.54(15) . . ?
N6 C8A C7A 102.59(14) . . ?
C23 C22 C21 117.56(17) . . ?
C13 C12 C11 120.81(16) . . ?
N5 C1A C2A 103.53(15) . . ?
C20 C21 C22 120.76(16) . . ?
N5 C4A C5A 108.46(12) . . ?
N5 C4A C3A 100.52(13) . . ?
C5A C4A C3A 117.93(15) . . ?
C4 C3 C2 102.54(15) . . ?
C5 C6 C7 103.73(15) . . ?
C5A C6A C7A 103.91(14) . . ?
C21A C20A C19A 120.82(15) . . ?
C6 C7 C8 105.60(14) . . ?
C12 C13 C14 121.41(16) . . ?
O2 C24 N4 125.12(15) . . ?
O2 C24 C17 126.15(15) . . ?
N4 C24 C17 108.67(13) . . ?
C4A C3A C2A 104.44(15) . . ?
C1 C2 C3 106.04(15) . . ?
C6A C7A C8A 106.03(14) . . ?
C3A C2A C1A 105.48(15) . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        28.38
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.436
_refine_diff_density_min         -0.194
_refine_diff_density_rms         0.050
_database_code_depnum_ccdc_archive 'CCDC 969349'
#######################################################################
#
#                 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
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  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_pb2

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H24 N4 O2'
_chemical_formula_sum            'C24 H24 N4 O2'
_chemical_formula_weight         400.47

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           Orthorhombic
_symmetry_space_group_name_H-M   Pbcn

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

_cell_length_a                   27.5591(13)
_cell_length_b                   9.5215(5)
_cell_length_c                   15.8189(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     4150.9(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      2.3
_cell_measurement_theta_max      25.0

_exptl_crystal_description       rectangular
_exptl_crystal_colour            white
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.29
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.282
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1696
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.6601
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   SADABS

_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  'INCOATEC Imus micro-focus source'
_diffrn_measurement_method       'Bruker D8 Venture PHOTON 100 CMOS'
_diffrn_detector_area_resol_mean 'omega scans'
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            18774
_diffrn_reflns_av_R_equivalents  0.0589
_diffrn_reflns_av_sigmaI/netI    0.0422
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.26
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3635
_reflns_number_gt                2790
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker, 2010)'
_computing_cell_refinement       'APEX2 (Bruker, 2010); SAINT (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009);XPREP(Sheldrick,2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_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)+(0.1116P)²+0.0502P] 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         3635
_refine_ls_number_parameters     279
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0752
_refine_ls_R_factor_gt           0.0561
_refine_ls_wR_factor_ref         0.1671
_refine_ls_wR_factor_gt          0.1566
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.049
_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
O1 O 0.47736(6) 0.00666(16) 0.09610(9) 0.0190(4) Uani 1 1 d . . .
O2 O 0.42143(6) -0.18112(17) 0.23493(10) 0.0239(4) Uani 1 1 d . . .
N2 N 0.32922(7) -0.00438(19) 0.19848(11) 0.0160(4) Uani 1 1 d . . .
N1 N 0.37904(7) -0.12235(18) 0.06374(11) 0.0151(4) Uani 1 1 d . . .
N4 N 0.44134(8) 0.1536(2) 0.00051(13) 0.0174(5) Uani 1 1 d . . .
N3 N 0.44324(7) 0.0348(2) 0.28452(12) 0.0211(5) Uani 1 1 d . . .
H3 H 0.4653 0.0075 0.3194 0.025 Uiso 1 1 calc R . .
C17 C 0.37955(8) 0.0379(2) 0.18439(14) 0.0156(5) Uani 1 1 d . . .
C9 C 0.38833(8) 0.0247(2) 0.08689(13) 0.0139(5) Uani 1 1 d . . .
C11 C 0.31216(8) 0.1679(2) 0.02737(14) 0.0167(5) Uani 1 1 d . . .
H11 H 0.2891 0.1243 0.0614 0.020 Uiso 1 1 calc R . .
C1 C 0.38916(9) -0.1635(2) -0.02402(14) 0.0196(5) Uani 1 1 d . . .
H1A H 0.4237 -0.1762 -0.0330 0.023 Uiso 1 1 calc R . .
H1B H 0.3772 -0.0934 -0.0634 0.023 Uiso 1 1 calc R . .
C13 C 0.33209(9) 0.3347(2) -0.08157(15) 0.0225(6) Uani 1 1 d . . .
H13 H 0.3219 0.4025 -0.1200 0.027 Uiso 1 1 calc R . .
C15 C 0.39416(8) 0.2005(2) -0.01836(14) 0.0168(5) Uani 1 1 d . . .
C23 C 0.43044(8) 0.1756(3) 0.27229(14) 0.0190(5) Uani 1 1 d . . .
C10 C 0.36080(8) 0.1319(2) 0.03365(13) 0.0131(5) Uani 1 1 d . . .
C22 C 0.45221(9) 0.2928(3) 0.30693(15) 0.0250(6) Uani 1 1 d . . .
H22 H 0.4784 0.2847 0.3438 0.030 Uiso 1 1 calc R . .
C4 C 0.32884(8) -0.1675(2) 0.07979(14) 0.0174(5) Uani 1 1 d . . .
H4A H 0.3066 -0.1103 0.0459 0.021 Uiso 1 1 calc R . .
C8 C 0.31007(9) 0.0061(3) 0.28458(14) 0.0217(6) Uani 1 1 d . . .
H8A H 0.3070 0.1034 0.3021 0.026 Uiso 1 1 calc R . .
H8B H 0.3306 -0.0432 0.3245 0.026 Uiso 1 1 calc R . .
C18 C 0.39145(8) 0.1849(2) 0.21571(13) 0.0168(5) Uani 1 1 d . . .
C7 C 0.26049(9) -0.0641(3) 0.27688(15) 0.0261(6) Uani 1 1 d . . .
H7A H 0.2351 0.0056 0.2709 0.031 Uiso 1 1 calc R . .
H7B H 0.2537 -0.1211 0.3263 0.031 Uiso 1 1 calc R . .
C12 C 0.29838(9) 0.2701(2) -0.03053(14) 0.0199(5) Uani 1 1 d . . .
H12 H 0.2659 0.2952 -0.0349 0.024 Uiso 1 1 calc R . .
C16 C 0.44158(8) 0.0587(2) 0.06331(14) 0.0142(5) Uani 1 1 d . . .
C21 C 0.43380(9) 0.4223(3) 0.28495(16) 0.0297(6) Uani 1 1 d . . .
H21 H 0.4483 0.5031 0.3063 0.036 Uiso 1 1 calc R . .
C14 C 0.38107(9) 0.3004(2) -0.07665(15) 0.0220(6) Uani 1 1 d . . .
H14 H 0.4039 0.3433 -0.1113 0.026 Uiso 1 1 calc R . .
C24 C 0.41706(8) -0.0538(3) 0.23532(14) 0.0181(5) Uani 1 1 d . . .
C19 C 0.37279(9) 0.3157(3) 0.19650(15) 0.0237(6) Uani 1 1 d . . .
H19 H 0.3463 0.3241 0.1605 0.028 Uiso 1 1 calc R . .
C3 C 0.32999(9) -0.3165(2) 0.04479(15) 0.0223(6) Uani 1 1 d . . .
H3A H 0.2976 -0.3486 0.0302 0.027 Uiso 1 1 calc R . .
H3B H 0.3442 -0.3812 0.0851 0.027 Uiso 1 1 calc R . .
C2 C 0.36194(10) -0.3021(3) -0.03438(17) 0.0306(6) Uani 1 1 d . . .
H2A H 0.3845 -0.3800 -0.0383 0.037 Uiso 1 1 calc R . .
H2B H 0.3421 -0.3005 -0.0850 0.037 Uiso 1 1 calc R . .
C6 C 0.26389(9) -0.1568(3) 0.19676(15) 0.0245(6) Uani 1 1 d . . .
H6A H 0.2545 -0.2528 0.2089 0.029 Uiso 1 1 calc R . .
H6B H 0.2434 -0.1203 0.1520 0.029 Uiso 1 1 calc R . .
C5 C 0.31734(9) -0.1483(2) 0.17234(15) 0.0179(5) Uani 1 1 d . . .
C20 C 0.39400(10) 0.4347(3) 0.23147(16) 0.0295(6) Uani 1 1 d . . .
H20 H 0.3815 0.5230 0.2190 0.035 Uiso 1 1 calc R . .
H5 H 0.3354(10) -0.217(3) 0.2033(15) 0.022(7) Uiso 1 1 d . . .
H4 H 0.4640(10) 0.182(3) -0.0248(18) 0.024(8) Uiso 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
O1 C16 1.220(3) . ?
O2 C24 1.218(3) . ?
N2 C17 1.462(3) . ?
N2 C8 1.464(3) . ?
N2 C5 1.469(3) . ?
N1 C1 1.469(3) . ?
N1 C9 1.470(3) . ?
N1 C4 1.471(3) . ?
N4 C16 1.343(3) . ?
N4 C15 1.407(3) . ?
N3 C24 1.356(3) . ?
N3 C23 1.400(3) . ?
C17 C18 1.520(3) . ?
C17 C9 1.566(3) . ?
C17 C24 1.575(3) . ?
C9 C10 1.526(3) . ?
C9 C16 1.548(3) . ?
C11 C10 1.387(3) . ?
C11 C12 1.389(3) . ?
C1 C2 1.527(3) . ?
C13 C12 1.376(3) . ?
C13 C14 1.391(3) . ?
C15 C14 1.373(3) . ?
C15 C10 1.396(3) . ?
C23 C22 1.381(3) . ?
C23 C18 1.401(3) . ?
C22 C21 1.378(4) . ?
C4 C5 1.509(3) . ?
C4 C3 1.523(3) . ?
C8 C7 1.526(3) . ?
C18 C19 1.382(3) . ?
C7 C6 1.547(3) . ?
C21 C20 1.390(4) . ?
C19 C20 1.389(4) . ?
C3 C2 1.537(3) . ?
C6 C5 1.525(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
C17 N2 C8 117.72(17) . . ?
C17 N2 C5 115.21(17) . . ?
C8 N2 C5 104.20(17) . . ?
C1 N1 C9 117.14(17) . . ?
C1 N1 C4 105.30(17) . . ?
C9 N1 C4 113.54(17) . . ?
C16 N4 C15 112.0(2) . . ?
C24 N3 C23 112.48(19) . . ?
N2 C17 C18 114.13(18) . . ?
N2 C17 C9 105.93(17) . . ?
C18 C17 C9 111.22(18) . . ?
N2 C17 C24 113.07(18) . . ?
C18 C17 C24 101.68(18) . . ?
C9 C17 C24 110.95(17) . . ?
N1 C9 C10 114.41(17) . . ?
N1 C9 C16 107.74(17) . . ?
C10 C9 C16 101.43(17) . . ?
N1 C9 C17 107.18(17) . . ?
C10 C9 C17 114.38(17) . . ?
C16 C9 C17 111.51(17) . . ?
C10 C11 C12 119.0(2) . . ?
N1 C1 C2 103.79(19) . . ?
C12 C13 C14 121.2(2) . . ?
C14 C15 C10 123.1(2) . . ?
C14 C15 N4 127.2(2) . . ?
C10 C15 N4 109.62(19) . . ?
C22 C23 N3 127.6(2) . . ?
C22 C23 C18 122.4(2) . . ?
N3 C23 C18 110.0(2) . . ?
C11 C10 C15 118.6(2) . . ?
C11 C10 C9 133.3(2) . . ?
C15 C10 C9 108.09(19) . . ?
C21 C22 C23 117.6(2) . . ?
N1 C4 C5 109.25(18) . . ?
N1 C4 C3 100.95(17) . . ?
C5 C4 C3 118.02(19) . . ?
N2 C8 C7 102.63(18) . . ?
C19 C18 C23 118.9(2) . . ?
C19 C18 C17 132.7(2) . . ?
C23 C18 C17 108.37(19) . . ?
C8 C7 C6 105.13(18) . . ?
C13 C12 C11 121.0(2) . . ?
O1 C16 N4 126.3(2) . . ?
O1 C16 C9 125.4(2) . . ?
N4 C16 C9 108.33(18) . . ?
C22 C21 C20 121.3(2) . . ?
C15 C14 C13 117.1(2) . . ?
O2 C24 N3 124.7(2) . . ?
O2 C24 C17 127.9(2) . . ?
N3 C24 C17 107.3(2) . . ?
C18 C19 C20 119.4(2) . . ?
C4 C3 C2 103.03(19) . . ?
C1 C2 C3 105.71(19) . . ?
C5 C6 C7 103.66(19) . . ?
N2 C5 C4 109.83(18) . . ?
N2 C5 C6 101.13(18) . . ?
C4 C5 C6 116.3(2) . . ?
C19 C20 C21 120.3(2) . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.372
_refine_diff_density_min         -0.422
_refine_diff_density_rms         0.132
_database_code_depnum_ccdc_archive 'CCDC 969350'
