 
data_shelxl 
 
_audit_creation_method            SHELXL-97 
_chemical_name_systematic 
; 
 ? 
; 
_chemical_name_common             ? 
_chemical_melting_point           ? 
_chemical_formula_moiety          ? 
_chemical_formula_sum 
 'C28 H18 N2 O' 
_chemical_formula_weight          398.44 
_chemical_absolute_configuration  unk

 
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            monoclinic 
_symmetry_space_group_name_H-M    P21 
 
loop_ 
 _symmetry_equiv_pos_as_xyz 
 'x, y, z' 
 '-x, y+1/2, -z' 
 
_cell_length_a                    9.7010(9) 
_cell_length_b                    16.3311(15) 
_cell_length_c                    12.5479(12) 
_cell_angle_alpha                 90.00 
_cell_angle_beta                  96.057(6) 
_cell_angle_gamma                 90.00 
_cell_volume                      1976.8(3) 
_cell_formula_units_Z             4 
_cell_measurement_temperature     293(2) 
_cell_measurement_reflns_used     3421 
_cell_measurement_theta_min       2.6 
_cell_measurement_theta_max       24.5 
 
_exptl_crystal_description        block 
_exptl_crystal_colour             colourless 
_exptl_crystal_size_max           0.30 
_exptl_crystal_size_mid           0.20 
_exptl_crystal_size_min           0.20 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_diffrn     1.339 
_exptl_crystal_density_method     'not measured' 
_exptl_crystal_F_000              832 
_exptl_absorpt_coefficient_mu     0.082 
_exptl_absorpt_correction_type    multi-scan 
_exptl_absorpt_correction_T_min   0.951 
_exptl_absorpt_correction_T_max   0.990
_exptl_absorpt_process_details    'SADABS (Bruker, 1999)' 
 
_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  
 'Bruker axs kappa apex2 CCD Diffractometer'
_diffrn_measurement_method        'ω and φ scan' 
_diffrn_detector_area_resol_mean  ? 
_diffrn_standards_number          ? 
_diffrn_standards_interval_count  ? 
_diffrn_standards_interval_time   ? 
_diffrn_standards_decay_%         0 
_diffrn_reflns_number             26378 
_diffrn_reflns_av_R_equivalents   0.0632 
_diffrn_reflns_av_sigmaI/netI     0.0662 
_diffrn_reflns_limit_h_min        -11 
_diffrn_reflns_limit_h_max        11 
_diffrn_reflns_limit_k_min        -19 
_diffrn_reflns_limit_k_max        19 
_diffrn_reflns_limit_l_min        -14 
_diffrn_reflns_limit_l_max        14 
_diffrn_reflns_theta_min          1.63 
_diffrn_reflns_theta_max          25.00 
_reflns_number_total              6830 
_reflns_number_gt                 3908 
_reflns_threshold_expression      >2sigma(I) 
 
_computing_data_collection        'APEX2 (Bruker, 2004)'
_computing_cell_refinement        'APEX2/SAINT (Bruker, 2004)' 
_computing_data_reduction         'SAINT/XPREP (Bruker, 2004)'
_computing_structure_solution     'SIR92 (Altornare et al., 1993)'
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics     
'ORTEP3 (Farrugia, 1997) and Mercury (Bruno et al., 2002)'
_computing_publication_material   'SHELXL-97 (Sheldrick, 2008)'
 
_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)+(0.1700P)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_abs_structure_details 
 'Flack H D (1983), Acta Cryst. A39, 876-881' 
_refine_ls_abs_structure_Flack    1(3) 
_refine_ls_number_reflns          6830 
_refine_ls_number_parameters      559 
_refine_ls_number_restraints      1 
_refine_ls_R_factor_all           0.1409 
_refine_ls_R_factor_gt            0.0875 
_refine_ls_wR_factor_ref          0.2682 
_refine_ls_wR_factor_gt           0.2123 
_refine_ls_goodness_of_fit_ref    1.012 
_refine_ls_restrained_S_all       1.012 
_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 0.2134(6) -0.0739(3) 0.9298(5) 0.0607(14) Uani 1 1 d . . . 
C2 C 0.1941(7) -0.1151(4) 1.0270(5) 0.0671(17) Uani 1 1 d . . . 
H2 H 0.2701 -0.1317 1.0733 0.081 Uiso 1 1 calc R . . 
C3 C 0.0646(7) -0.1300(4) 1.0510(5) 0.0702(17) Uani 1 1 d . . . 
H3 H 0.0526 -0.1573 1.1144 0.084 Uiso 1 1 calc R . . 
C4 C -0.0544(6) -0.1055(4) 0.9832(5) 0.0607(16) Uani 1 1 d . . . 
C5 C -0.1884(7) -0.1205(4) 1.0124(5) 0.0693(16) Uani 1 1 d . . . 
H5 H -0.1990 -0.1475 1.0763 0.083 Uiso 1 1 calc R . . 
C6 C -0.3042(6) -0.0954(4) 0.9468(5) 0.0771(18) Uani 1 1 d . . . 
H6 H -0.3926 -0.1054 0.9661 0.093 Uiso 1 1 calc R . . 
C7 C -0.2864(6) -0.0555(5) 0.8528(5) 0.0826(19) Uani 1 1 d . . . 
H7 H -0.3646 -0.0381 0.8095 0.099 Uiso 1 1 calc R . . 
C8 C -0.1584(5) -0.0403(5) 0.8202(5) 0.078(2) Uani 1 1 d . . . 
H8 H -0.1509 -0.0138 0.7555 0.094 Uiso 1 1 calc R . . 
C9 C -0.0355(5) -0.0657(3) 0.8863(4) 0.0531(13) Uani 1 1 d . . . 
C10 C 0.1010(5) -0.0509(3) 0.8581(4) 0.0495(13) Uani 1 1 d . . . 
C11 C 0.1249(6) -0.0112(4) 0.7568(5) 0.0591(15) Uani 1 1 d . . . 
H11 H 0.0495 0.0053 0.7098 0.071 Uiso 1 1 calc R . . 
C12 C 0.3732(6) 0.0586(4) 0.6131(5) 0.0521(12) Uani 1 1 d . . . 
H12 H 0.4473 0.0464 0.6638 0.062 Uiso 1 1 calc R . . 
C13 C 0.3989(5) 0.0994(3) 0.5141(4) 0.0496(13) Uani 1 1 d . . . 
C14 C 0.2871(5) 0.1149(4) 0.4361(5) 0.0648(15) Uani 1 1 d . . . 
H14 H 0.1987 0.0981 0.4488 0.078 Uiso 1 1 calc R . . 
C15 C 0.3042(6) 0.1533(3) 0.3434(5) 0.0642(16) Uani 1 1 d . . . 
H15 H 0.2274 0.1623 0.2939 0.077 Uiso 1 1 calc R . . 
C16 C 0.4325(5) 0.1796(3) 0.3202(4) 0.0502(13) Uani 1 1 d . . . 
C17 C 0.4540(7) 0.2199(4) 0.2241(5) 0.0744(18) Uani 1 1 d . . . 
H17 H 0.3776 0.2301 0.1747 0.089 Uiso 1 1 calc R . . 
C18 C 0.5796(7) 0.2445(4) 0.2001(6) 0.078(2) Uani 1 1 d . . . 
H18 H 0.5882 0.2709 0.1354 0.093 Uiso 1 1 calc R . . 
C19 C 0.7009(6) 0.2299(3) 0.2749(5) 0.0619(15) Uani 1 1 d . . . 
C20 C 0.8307(8) 0.2534(4) 0.2537(6) 0.0747(19) Uani 1 1 d . . . 
H20 H 0.8413 0.2773 0.1878 0.090 Uiso 1 1 calc R . . 
C21 C 0.9458(7) 0.2431(4) 0.3261(7) 0.082(2) Uani 1 1 d . . . 
H21 H 1.0321 0.2618 0.3107 0.098 Uiso 1 1 calc R . . 
C22 C 0.9309(6) 0.2038(4) 0.4238(6) 0.0739(18) Uani 1 1 d . . . 
H22 H 1.0083 0.1954 0.4729 0.089 Uiso 1 1 calc R . . 
C23 C 0.8013(5) 0.1773(3) 0.4477(5) 0.0542(13) Uani 1 1 d . . . 
C24 C 0.7796(5) 0.1371(3) 0.5455(5) 0.0603(15) Uani 1 1 d . . . 
H24 H 0.8554 0.1283 0.5960 0.072 Uiso 1 1 calc R . . 
C25 C 0.6555(5) 0.1117(3) 0.5673(5) 0.0592(14) Uani 1 1 d . . . 
H25 H 0.6481 0.0849 0.6318 0.071 Uiso 1 1 calc R . . 
C26 C 0.5323(5) 0.1240(3) 0.4947(4) 0.0438(12) Uani 1 1 d . . . 
C27 C 0.5504(5) 0.1642(3) 0.3951(4) 0.0486(12) Uani 1 1 d . . . 
C28 C 0.6830(5) 0.1897(3) 0.3723(4) 0.0484(13) Uani 1 1 d . . . 
C29 C -0.0653(5) 0.6912(3) 1.1771(4) 0.0527(13) Uani 1 1 d . . . 
C30 C -0.0889(5) 0.7310(4) 1.2729(5) 0.0602(16) Uani 1 1 d . . . 
H30 H -0.0141 0.7470 1.3209 0.072 Uiso 1 1 calc R . . 
C31 C -0.2204(6) 0.7463(3) 1.2960(4) 0.0561(14) Uani 1 1 d . . . 
H31 H -0.2336 0.7733 1.3594 0.067 Uiso 1 1 calc R . . 
C32 C -0.3371(5) 0.7225(3) 1.2266(4) 0.0472(13) Uani 1 1 d . . . 
C33 C -0.4722(5) 0.7353(3) 1.2522(4) 0.0571(14) Uani 1 1 d . . . 
H33 H -0.4860 0.7610 1.3164 0.069 Uiso 1 1 calc R . . 
C34 C -0.5837(5) 0.7110(4) 1.1853(5) 0.0656(16) Uani 1 1 d . . . 
H34 H -0.6732 0.7204 1.2028 0.079 Uiso 1 1 calc R . . 
C35 C -0.5620(5) 0.6717(4) 1.0898(5) 0.0734(17) Uani 1 1 d . . . 
H35 H -0.6383 0.6548 1.0439 0.088 Uiso 1 1 calc R . . 
C36 C -0.4343(5) 0.6575(4) 1.0624(4) 0.0612(15) Uani 1 1 d . . . 
H36 H -0.4244 0.6312 0.9979 0.073 Uiso 1 1 calc R . . 
C37 C -0.3148(5) 0.6812(3) 1.1284(4) 0.0438(11) Uani 1 1 d . . . 
C38 C -0.1748(5) 0.6680(3) 1.1041(4) 0.0421(12) Uani 1 1 d . . . 
C39 C -0.1478(5) 0.6305(3) 1.0042(4) 0.0525(13) Uani 1 1 d . . . 
H39 H -0.2223 0.6148 0.9557 0.063 Uiso 1 1 calc R . . 
C40 C 0.1028(5) 0.5613(3) 0.8614(4) 0.0455(12) Uani 1 1 d . . . 
H40 H 0.1768 0.5717 0.9130 0.055 Uiso 1 1 calc R . . 
C41 C 0.1292(5) 0.5224(3) 0.7628(4) 0.0431(11) Uani 1 1 d . . . 
C42 C 0.0164(5) 0.5062(3) 0.6843(4) 0.0592(14) Uani 1 1 d . . . 
H42 H -0.0724 0.5216 0.6979 0.071 Uiso 1 1 calc R . . 
C43 C 0.0338(6) 0.4692(3) 0.5903(4) 0.0623(15) Uani 1 1 d . . . 
H43 H -0.0423 0.4609 0.5400 0.075 Uiso 1 1 calc R . . 
C44 C 0.1644(5) 0.4433(3) 0.5682(4) 0.0456(12) Uani 1 1 d . . . 
C45 C 0.1847(7) 0.4031(3) 0.4672(4) 0.0686(16) Uani 1 1 d . . . 
H45 H 0.1094 0.3937 0.4164 0.082 Uiso 1 1 calc R . . 
C46 C 0.3110(8) 0.3800(4) 0.4479(5) 0.0711(18) Uani 1 1 d . . . 
H46 H 0.3204 0.3535 0.3835 0.085 Uiso 1 1 calc R . . 
C47 C 0.4315(7) 0.3929(3) 0.5188(5) 0.0602(15) Uani 1 1 d . . . 
C48 C 0.5619(8) 0.3687(4) 0.4995(6) 0.0750(19) Uani 1 1 d . . . 
H48 H 0.5746 0.3441 0.4344 0.090 Uiso 1 1 calc R . . 
C49 C 0.6745(7) 0.3801(4) 0.5745(6) 0.081(2) Uani 1 1 d . . . 
H49 H 0.7614 0.3615 0.5606 0.097 Uiso 1 1 calc R . . 
C50 C 0.6594(6) 0.4185(4) 0.6691(5) 0.0690(16) Uani 1 1 d . . . 
H50 H 0.7371 0.4260 0.7183 0.083 Uiso 1 1 calc R . . 
C51 C 0.5319(5) 0.4468(3) 0.6946(4) 0.0511(12) Uani 1 1 d . . . 
C52 C 0.5116(5) 0.4864(3) 0.7916(4) 0.0526(13) Uani 1 1 d . . . 
H52 H 0.5876 0.4957 0.8418 0.063 Uiso 1 1 calc R . . 
C53 C 0.3842(5) 0.5113(3) 0.8138(4) 0.0498(13) Uani 1 1 d . . . 
H53 H 0.3758 0.5381 0.8782 0.060 Uiso 1 1 calc R . . 
C54 C 0.2638(5) 0.4978(3) 0.7422(4) 0.0395(12) Uani 1 1 d . . . 
C55 C 0.2815(5) 0.4586(3) 0.6431(4) 0.0421(11) Uani 1 1 d . . . 
C56 C 0.4144(5) 0.4335(3) 0.6193(4) 0.0460(13) Uani 1 1 d . . . 
N1 N 0.2466(5) 0.0008(3) 0.7324(4) 0.0632(14) Uani 1 1 d . . . 
N2 N 0.2507(5) 0.0394(3) 0.6315(4) 0.0632(12) Uani 1 1 d . . . 
N3 N -0.0235(4) 0.6182(3) 0.9803(4) 0.0523(12) Uani 1 1 d . . . 
N4 N -0.0193(4) 0.5820(3) 0.8801(3) 0.0561(11) Uani 1 1 d . . . 
O1 O 0.3453(4) -0.0606(3) 0.9118(3) 0.0770(13) Uani 1 1 d . . . 
H1 H 0.3471 -0.0379 0.8536 0.116 Uiso 1 1 calc R . . 
O2 O 0.0679(3) 0.6784(3) 1.1626(3) 0.0691(12) Uani 1 1 d . . . 
H2A H 0.0724 0.6481 1.1110 0.104 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 
C1 O1 1.340(6) . ? 
C1 C10 1.390(8) . ? 
C1 C2 1.423(8) . ? 
C2 C3 1.345(8) . ? 
C2 H2 0.9300 . ? 
C3 C4 1.417(8) . ? 
C3 H3 0.9300 . ? 
C4 C9 1.408(8) . ? 
C4 C5 1.409(7) . ? 
C5 C6 1.382(9) . ? 
C5 H5 0.9300 . ? 
C6 C7 1.374(8) . ? 
C6 H6 0.9300 . ? 
C7 C8 1.371(7) . ? 
C7 H7 0.9300 . ? 
C8 C9 1.439(8) . ? 
C8 H8 0.9300 . ? 
C9 C10 1.427(7) . ? 
C10 C11 1.466(8) . ? 
C11 N1 1.266(6) . ? 
C11 H11 0.9300 . ? 
C12 N2 1.273(6) . ? 
C12 C13 1.454(8) . ? 
C12 H12 0.9300 . ? 
C13 C26 1.401(7) . ? 
C13 C14 1.405(7) . ? 
C14 C15 1.347(8) . ? 
C14 H14 0.9300 . ? 
C15 C16 1.376(7) . ? 
C15 H15 0.9300 . ? 
C16 C17 1.409(7) . ? 
C16 C27 1.425(7) . ? 
C17 C18 1.347(8) . ? 
C17 H17 0.9300 . ? 
C18 C19 1.446(9) . ? 
C18 H18 0.9300 . ? 
C19 C20 1.369(8) . ? 
C19 C28 1.413(7) . ? 
C20 C21 1.374(10) . ? 
C20 H20 0.9300 . ? 
C21 C22 1.404(9) . ? 
C21 H21 0.9300 . ? 
C22 C23 1.392(7) . ? 
C22 H22 0.9300 . ? 
C23 C28 1.424(7) . ? 
C23 C24 1.426(7) . ? 
C24 C25 1.329(7) . ? 
C24 H24 0.9300 . ? 
C25 C26 1.439(7) . ? 
C25 H25 0.9300 . ? 
C26 C27 1.439(7) . ? 
C27 C28 1.409(7) . ? 
C29 O2 1.341(6) . ? 
C29 C38 1.380(7) . ? 
C29 C30 1.407(7) . ? 
C30 C31 1.360(7) . ? 
C30 H30 0.9300 . ? 
C31 C32 1.409(7) . ? 
C31 H31 0.9300 . ? 
C32 C33 1.398(6) . ? 
C32 C37 1.440(6) . ? 
C33 C34 1.356(7) . ? 
C33 H33 0.9300 . ? 
C34 C35 1.395(8) . ? 
C34 H34 0.9300 . ? 
C35 C36 1.341(7) . ? 
C35 H35 0.9300 . ? 
C36 C37 1.406(7) . ? 
C36 H36 0.9300 . ? 
C37 C38 1.439(6) . ? 
C38 C39 1.444(7) . ? 
C39 N3 1.289(6) . ? 
C39 H39 0.9300 . ? 
C40 N4 1.277(6) . ? 
C40 C41 1.438(7) . ? 
C40 H40 0.9300 . ? 
C41 C54 1.415(6) . ? 
C41 C42 1.417(7) . ? 
C42 C43 1.353(7) . ? 
C42 H42 0.9300 . ? 
C43 C44 1.390(6) . ? 
C43 H43 0.9300 . ? 
C44 C55 1.418(6) . ? 
C44 C45 1.459(7) . ? 
C45 C46 1.328(8) . ? 
C45 H45 0.9300 . ? 
C46 C47 1.408(9) . ? 
C46 H46 0.9300 . ? 
C47 C48 1.372(8) . ? 
C47 C56 1.450(7) . ? 
C48 C49 1.378(10) . ? 
C48 H48 0.9300 . ? 
C49 C50 1.364(8) . ? 
C49 H49 0.9300 . ? 
C50 C51 1.388(7) . ? 
C50 H50 0.9300 . ? 
C51 C52 1.411(7) . ? 
C51 C56 1.418(7) . ? 
C52 C53 1.358(6) . ? 
C52 H52 0.9300 . ? 
C53 C54 1.413(7) . ? 
C53 H53 0.9300 . ? 
C54 C55 1.425(6) . ? 
C55 C56 1.414(6) . ? 
N1 N2 1.418(6) . ? 
N3 N4 1.393(6) . ? 
O1 H1 0.8200 . ? 
O2 H2A 0.8200 . ? 
 
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 
O1 C1 C10 123.0(6) . . ? 
O1 C1 C2 115.8(5) . . ? 
C10 C1 C2 121.2(5) . . ? 
C3 C2 C1 119.2(6) . . ? 
C3 C2 H2 120.4 . . ? 
C1 C2 H2 120.4 . . ? 
C2 C3 C4 122.4(6) . . ? 
C2 C3 H3 118.8 . . ? 
C4 C3 H3 118.8 . . ? 
C9 C4 C5 120.8(6) . . ? 
C9 C4 C3 118.5(5) . . ? 
C5 C4 C3 120.7(6) . . ? 
C6 C5 C4 120.6(6) . . ? 
C6 C5 H5 119.7 . . ? 
C4 C5 H5 119.7 . . ? 
C7 C6 C5 118.9(5) . . ? 
C7 C6 H6 120.5 . . ? 
C5 C6 H6 120.5 . . ? 
C8 C7 C6 122.8(6) . . ? 
C8 C7 H7 118.6 . . ? 
C6 C7 H7 118.6 . . ? 
C7 C8 C9 119.8(6) . . ? 
C7 C8 H8 120.1 . . ? 
C9 C8 H8 120.1 . . ? 
C4 C9 C10 120.0(5) . . ? 
C4 C9 C8 117.1(5) . . ? 
C10 C9 C8 122.9(5) . . ? 
C1 C10 C9 118.6(5) . . ? 
C1 C10 C11 119.7(5) . . ? 
C9 C10 C11 121.7(5) . . ? 
N1 C11 C10 121.0(5) . . ? 
N1 C11 H11 119.5 . . ? 
C10 C11 H11 119.5 . . ? 
N2 C12 C13 121.0(5) . . ? 
N2 C12 H12 119.5 . . ? 
C13 C12 H12 119.5 . . ? 
C26 C13 C14 119.1(5) . . ? 
C26 C13 C12 121.7(5) . . ? 
C14 C13 C12 119.3(5) . . ? 
C15 C14 C13 122.0(5) . . ? 
C15 C14 H14 119.0 . . ? 
C13 C14 H14 119.0 . . ? 
C14 C15 C16 121.6(5) . . ? 
C14 C15 H15 119.2 . . ? 
C16 C15 H15 119.2 . . ? 
C15 C16 C17 123.1(5) . . ? 
C15 C16 C27 119.1(5) . . ? 
C17 C16 C27 117.8(5) . . ? 
C18 C17 C16 123.4(6) . . ? 
C18 C17 H17 118.3 . . ? 
C16 C17 H17 118.3 . . ? 
C17 C18 C19 119.9(6) . . ? 
C17 C18 H18 120.0 . . ? 
C19 C18 H18 120.0 . . ? 
C20 C19 C28 119.9(6) . . ? 
C20 C19 C18 122.0(6) . . ? 
C28 C19 C18 118.2(5) . . ? 
C19 C20 C21 122.5(7) . . ? 
C19 C20 H20 118.8 . . ? 
C21 C20 H20 118.8 . . ? 
C20 C21 C22 118.8(6) . . ? 
C20 C21 H21 120.6 . . ? 
C22 C21 H21 120.6 . . ? 
C23 C22 C21 120.6(6) . . ? 
C23 C22 H22 119.7 . . ? 
C21 C22 H22 119.7 . . ? 
C22 C23 C28 119.7(5) . . ? 
C22 C23 C24 123.2(5) . . ? 
C28 C23 C24 117.1(5) . . ? 
C25 C24 C23 122.7(5) . . ? 
C25 C24 H24 118.7 . . ? 
C23 C24 H24 118.7 . . ? 
C24 C25 C26 122.5(6) . . ? 
C24 C25 H25 118.8 . . ? 
C26 C25 H25 118.8 . . ? 
C13 C26 C25 124.8(5) . . ? 
C13 C26 C27 118.8(4) . . ? 
C25 C26 C27 116.3(5) . . ? 
C28 C27 C16 120.0(5) . . ? 
C28 C27 C26 120.6(5) . . ? 
C16 C27 C26 119.3(5) . . ? 
C27 C28 C19 120.7(5) . . ? 
C27 C28 C23 120.8(5) . . ? 
C19 C28 C23 118.5(5) . . ? 
O2 C29 C38 123.5(5) . . ? 
O2 C29 C30 115.7(4) . . ? 
C38 C29 C30 120.7(5) . . ? 
C31 C30 C29 120.5(5) . . ? 
C31 C30 H30 119.8 . . ? 
C29 C30 H30 119.8 . . ? 
C30 C31 C32 121.9(5) . . ? 
C30 C31 H31 119.1 . . ? 
C32 C31 H31 119.1 . . ? 
C33 C32 C31 121.9(5) . . ? 
C33 C32 C37 119.7(5) . . ? 
C31 C32 C37 118.3(5) . . ? 
C34 C33 C32 121.3(5) . . ? 
C34 C33 H33 119.3 . . ? 
C32 C33 H33 119.3 . . ? 
C33 C34 C35 118.9(5) . . ? 
C33 C34 H34 120.5 . . ? 
C35 C34 H34 120.5 . . ? 
C36 C35 C34 121.8(5) . . ? 
C36 C35 H35 119.1 . . ? 
C34 C35 H35 119.1 . . ? 
C35 C36 C37 121.9(5) . . ? 
C35 C36 H36 119.1 . . ? 
C37 C36 H36 119.1 . . ? 
C36 C37 C38 124.8(4) . . ? 
C36 C37 C32 116.4(4) . . ? 
C38 C37 C32 118.8(4) . . ? 
C29 C38 C37 119.7(5) . . ? 
C29 C38 C39 119.7(5) . . ? 
C37 C38 C39 120.6(4) . . ? 
N3 C39 C38 121.9(5) . . ? 
N3 C39 H39 119.0 . . ? 
C38 C39 H39 119.0 . . ? 
N4 C40 C41 121.9(4) . . ? 
N4 C40 H40 119.1 . . ? 
C41 C40 H40 119.1 . . ? 
C54 C41 C42 118.7(4) . . ? 
C54 C41 C40 122.2(4) . . ? 
C42 C41 C40 119.0(4) . . ? 
C43 C42 C41 122.0(5) . . ? 
C43 C42 H42 119.0 . . ? 
C41 C42 H42 119.0 . . ? 
C42 C43 C44 120.7(5) . . ? 
C42 C43 H43 119.6 . . ? 
C44 C43 H43 119.6 . . ? 
C43 C44 C55 119.8(4) . . ? 
C43 C44 C45 121.3(5) . . ? 
C55 C44 C45 118.9(5) . . ? 
C46 C45 C44 119.9(5) . . ? 
C46 C45 H45 120.1 . . ? 
C44 C45 H45 120.1 . . ? 
C45 C46 C47 124.2(6) . . ? 
C45 C46 H46 117.9 . . ? 
C47 C46 H46 117.9 . . ? 
C48 C47 C46 124.4(6) . . ? 
C48 C47 C56 118.6(6) . . ? 
C46 C47 C56 117.0(5) . . ? 
C47 C48 C49 121.3(6) . . ? 
C47 C48 H48 119.4 . . ? 
C49 C48 H48 119.4 . . ? 
C50 C49 C48 120.5(6) . . ? 
C50 C49 H49 119.8 . . ? 
C48 C49 H49 119.8 . . ? 
C49 C50 C51 122.2(6) . . ? 
C49 C50 H50 118.9 . . ? 
C51 C50 H50 118.9 . . ? 
C50 C51 C52 124.0(5) . . ? 
C50 C51 C56 118.0(5) . . ? 
C52 C51 C56 118.0(4) . . ? 
C53 C52 C51 121.8(5) . . ? 
C53 C52 H52 119.1 . . ? 
C51 C52 H52 119.1 . . ? 
C52 C53 C54 122.2(5) . . ? 
C52 C53 H53 118.9 . . ? 
C54 C53 H53 118.9 . . ? 
C53 C54 C41 123.8(5) . . ? 
C53 C54 C55 117.2(4) . . ? 
C41 C54 C55 119.0(4) . . ? 
C56 C55 C44 119.6(4) . . ? 
C56 C55 C54 120.7(4) . . ? 
C44 C55 C54 119.7(4) . . ? 
C55 C56 C51 120.2(5) . . ? 
C55 C56 C47 120.4(5) . . ? 
C51 C56 C47 119.4(5) . . ? 
C11 N1 N2 113.6(5) . . ? 
C12 N2 N1 112.7(5) . . ? 
C39 N3 N4 113.2(4) . . ? 
C40 N4 N3 113.2(4) . . ? 
C1 O1 H1 109.5 . . ? 
C29 O2 H2A 109.5 . . ? 
 
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 
O1 C1 C2 C3 179.4(5) . . . . ? 
C10 C1 C2 C3 -1.9(8) . . . . ? 
C1 C2 C3 C4 -0.4(9) . . . . ? 
C2 C3 C4 C9 1.2(9) . . . . ? 
C2 C3 C4 C5 -178.5(6) . . . . ? 
C9 C4 C5 C6 -0.7(9) . . . . ? 
C3 C4 C5 C6 179.0(6) . . . . ? 
C4 C5 C6 C7 -0.1(9) . . . . ? 
C5 C6 C7 C8 0.9(10) . . . . ? 
C6 C7 C8 C9 -0.8(10) . . . . ? 
C5 C4 C9 C10 179.9(5) . . . . ? 
C3 C4 C9 C10 0.2(8) . . . . ? 
C5 C4 C9 C8 0.8(8) . . . . ? 
C3 C4 C9 C8 -178.9(5) . . . . ? 
C7 C8 C9 C4 0.0(9) . . . . ? 
C7 C8 C9 C10 -179.1(6) . . . . ? 
O1 C1 C10 C9 -178.2(5) . . . . ? 
C2 C1 C10 C9 3.2(8) . . . . ? 
O1 C1 C10 C11 0.9(8) . . . . ? 
C2 C1 C10 C11 -177.7(5) . . . . ? 
C4 C9 C10 C1 -2.3(7) . . . . ? 
C8 C9 C10 C1 176.7(5) . . . . ? 
C4 C9 C10 C11 178.6(5) . . . . ? 
C8 C9 C10 C11 -2.4(8) . . . . ? 
C1 C10 C11 N1 1.6(8) . . . . ? 
C9 C10 C11 N1 -179.3(5) . . . . ? 
N2 C12 C13 C26 177.3(5) . . . . ? 
N2 C12 C13 C14 -2.4(8) . . . . ? 
C26 C13 C14 C15 -0.5(8) . . . . ? 
C12 C13 C14 C15 179.2(5) . . . . ? 
C13 C14 C15 C16 -0.1(9) . . . . ? 
C14 C15 C16 C17 180.0(5) . . . . ? 
C14 C15 C16 C27 1.3(9) . . . . ? 
C15 C16 C17 C18 -178.8(6) . . . . ? 
C27 C16 C17 C18 -0.1(9) . . . . ? 
C16 C17 C18 C19 -0.1(10) . . . . ? 
C17 C18 C19 C20 179.6(6) . . . . ? 
C17 C18 C19 C28 -0.1(9) . . . . ? 
C28 C19 C20 C21 -3.2(9) . . . . ? 
C18 C19 C20 C21 177.1(6) . . . . ? 
C19 C20 C21 C22 2.8(10) . . . . ? 
C20 C21 C22 C23 -1.3(9) . . . . ? 
C21 C22 C23 C28 0.3(8) . . . . ? 
C21 C22 C23 C24 -179.9(5) . . . . ? 
C22 C23 C24 C25 -179.6(5) . . . . ? 
C28 C23 C24 C25 0.1(7) . . . . ? 
C23 C24 C25 C26 -1.2(8) . . . . ? 
C14 C13 C26 C25 -179.7(5) . . . . ? 
C12 C13 C26 C25 0.6(8) . . . . ? 
C14 C13 C26 C27 -0.1(7) . . . . ? 
C12 C13 C26 C27 -179.8(5) . . . . ? 
C24 C25 C26 C13 -179.2(5) . . . . ? 
C24 C25 C26 C27 1.2(7) . . . . ? 
C15 C16 C27 C28 179.2(5) . . . . ? 
C17 C16 C27 C28 0.5(7) . . . . ? 
C15 C16 C27 C26 -2.0(7) . . . . ? 
C17 C16 C27 C26 179.3(5) . . . . ? 
C13 C26 C27 C28 -179.8(4) . . . . ? 
C25 C26 C27 C28 -0.2(7) . . . . ? 
C13 C26 C27 C16 1.4(7) . . . . ? 
C25 C26 C27 C16 -179.0(5) . . . . ? 
C16 C27 C28 C19 -0.7(7) . . . . ? 
C26 C27 C28 C19 -179.5(4) . . . . ? 
C16 C27 C28 C23 178.0(5) . . . . ? 
C26 C27 C28 C23 -0.8(7) . . . . ? 
C20 C19 C28 C27 -179.3(5) . . . . ? 
C18 C19 C28 C27 0.5(8) . . . . ? 
C20 C19 C28 C23 2.1(8) . . . . ? 
C18 C19 C28 C23 -178.2(5) . . . . ? 
C22 C23 C28 C27 -179.4(5) . . . . ? 
C24 C23 C28 C27 0.9(7) . . . . ? 
C22 C23 C28 C19 -0.7(7) . . . . ? 
C24 C23 C28 C19 179.6(4) . . . . ? 
O2 C29 C30 C31 -179.4(5) . . . . ? 
C38 C29 C30 C31 1.0(9) . . . . ? 
C29 C30 C31 C32 0.7(9) . . . . ? 
C30 C31 C32 C33 177.4(5) . . . . ? 
C30 C31 C32 C37 -0.4(8) . . . . ? 
C31 C32 C33 C34 -179.1(5) . . . . ? 
C37 C32 C33 C34 -1.3(8) . . . . ? 
C32 C33 C34 C35 0.7(9) . . . . ? 
C33 C34 C35 C36 -0.2(10) . . . . ? 
C34 C35 C36 C37 0.2(10) . . . . ? 
C35 C36 C37 C38 180.0(5) . . . . ? 
C35 C36 C37 C32 -0.7(8) . . . . ? 
C33 C32 C37 C36 1.2(7) . . . . ? 
C31 C32 C37 C36 179.1(5) . . . . ? 
C33 C32 C37 C38 -179.4(4) . . . . ? 
C31 C32 C37 C38 -1.5(7) . . . . ? 
O2 C29 C38 C37 177.5(4) . . . . ? 
C30 C29 C38 C37 -3.0(8) . . . . ? 
O2 C29 C38 C39 -2.3(8) . . . . ? 
C30 C29 C38 C39 177.2(5) . . . . ? 
C36 C37 C38 C29 -177.5(5) . . . . ? 
C32 C37 C38 C29 3.2(7) . . . . ? 
C36 C37 C38 C39 2.3(8) . . . . ? 
C32 C37 C38 C39 -177.0(4) . . . . ? 
C29 C38 C39 N3 -0.4(8) . . . . ? 
C37 C38 C39 N3 179.8(5) . . . . ? 
N4 C40 C41 C54 -178.7(5) . . . . ? 
N4 C40 C41 C42 -0.3(8) . . . . ? 
C54 C41 C42 C43 -0.9(8) . . . . ? 
C40 C41 C42 C43 -179.4(5) . . . . ? 
C41 C42 C43 C44 1.7(8) . . . . ? 
C42 C43 C44 C55 -2.3(8) . . . . ? 
C42 C43 C44 C45 179.9(5) . . . . ? 
C43 C44 C45 C46 179.3(5) . . . . ? 
C55 C44 C45 C46 1.5(8) . . . . ? 
C44 C45 C46 C47 -1.3(9) . . . . ? 
C45 C46 C47 C48 179.6(6) . . . . ? 
C45 C46 C47 C56 0.7(9) . . . . ? 
C46 C47 C48 C49 -177.0(6) . . . . ? 
C56 C47 C48 C49 1.9(9) . . . . ? 
C47 C48 C49 C50 -2.2(10) . . . . ? 
C48 C49 C50 C51 0.6(9) . . . . ? 
C49 C50 C51 C52 179.7(5) . . . . ? 
C49 C50 C51 C56 1.0(8) . . . . ? 
C50 C51 C52 C53 -178.4(5) . . . . ? 
C56 C51 C52 C53 0.2(8) . . . . ? 
C51 C52 C53 C54 1.2(8) . . . . ? 
C52 C53 C54 C41 179.6(5) . . . . ? 
C52 C53 C54 C55 -1.7(7) . . . . ? 
C42 C41 C54 C53 179.3(5) . . . . ? 
C40 C41 C54 C53 -2.2(8) . . . . ? 
C42 C41 C54 C55 0.7(7) . . . . ? 
C40 C41 C54 C55 179.2(4) . . . . ? 
C43 C44 C55 C56 -178.9(4) . . . . ? 
C45 C44 C55 C56 -1.0(7) . . . . ? 
C43 C44 C55 C54 2.2(7) . . . . ? 
C45 C44 C55 C54 -180.0(4) . . . . ? 
C53 C54 C55 C56 0.9(6) . . . . ? 
C41 C54 C55 C56 179.7(4) . . . . ? 
C53 C54 C55 C44 179.9(4) . . . . ? 
C41 C54 C55 C44 -1.4(7) . . . . ? 
C44 C55 C56 C51 -178.6(4) . . . . ? 
C54 C55 C56 C51 0.4(7) . . . . ? 
C44 C55 C56 C47 0.4(7) . . . . ? 
C54 C55 C56 C47 179.4(4) . . . . ? 
C50 C51 C56 C55 177.8(4) . . . . ? 
C52 C51 C56 C55 -1.0(7) . . . . ? 
C50 C51 C56 C47 -1.2(7) . . . . ? 
C52 C51 C56 C47 -180.0(4) . . . . ? 
C48 C47 C56 C55 -179.2(5) . . . . ? 
C46 C47 C56 C55 -0.2(7) . . . . ? 
C48 C47 C56 C51 -0.2(7) . . . . ? 
C46 C47 C56 C51 178.8(5) . . . . ? 
C10 C11 N1 N2 179.7(5) . . . . ? 
C13 C12 N2 N1 -179.5(5) . . . . ? 
C11 N1 N2 C12 173.2(5) . . . . ? 
C38 C39 N3 N4 -179.5(4) . . . . ? 
C41 C40 N4 N3 179.5(5) . . . . ? 
C39 N3 N4 C40 -172.6(5) . . . . ? 
 
loop_ 
 _geom_hbond_atom_site_label_D 
 _geom_hbond_atom_site_label_H 
 _geom_hbond_atom_site_label_A 
 _geom_hbond_distance_DH 
 _geom_hbond_distance_HA 
 _geom_hbond_distance_DA 
 _geom_hbond_angle_DHA 
 _geom_hbond_site_symmetry_A 
O1 H1 N1  0.82 1.83 2.556(7) 146.7 . 
O2 H2A N3  0.82 1.86 2.561(6) 142.2 . 
 
_diffrn_measured_fraction_theta_max    0.999 
_diffrn_reflns_theta_full              25.00 
_diffrn_measured_fraction_theta_full   0.999 
_refine_diff_density_max    0.493 
_refine_diff_density_min   -0.290 
_refine_diff_density_rms    0.080 
