  
data_jr016m 
  
_audit_creation_method           SHELXL-97 
_chemical_name_systematic        ? 
_chemical_name_common            ? 
_chemical_melting_point          ? 
_chemical_formula_moiety         'C31 H29 N O5' 
_chemical_formula_sum            'C31 H29 N O5' 
_chemical_formula_weight         495.55 
  
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_int_tables_number      2 
  
loop_ 
_symmetry_equiv_pos_as_xyz 
'x, y, z' 
'-x, -y, -z' 
  
_cell_length_a                   9.6289(18) 
_cell_length_b                   12.161(2) 
_cell_length_c                   13.927(3) 
_cell_angle_alpha                75.761(4) 
_cell_angle_beta                 89.878(4) 
_cell_angle_gamma                70.641(4) 
_cell_volume                     1485.7(5) 
_cell_formula_units_Z            2 
_cell_measurement_temperature    297(2) 
_cell_measurement_reflns_used    2713 
_cell_measurement_theta_min      2.362 
_cell_measurement_theta_max      25.973 
  
_exptl_crystal_description       parallelepiped 
_exptl_crystal_colour            colorless 
_exptl_crystal_size_max          0.69 
_exptl_crystal_size_mid          0.55 
_exptl_crystal_size_min          0.46 
_exptl_crystal_density_meas      ? 
_exptl_crystal_density_diffrn    1.108 
_exptl_crystal_density_method    'not measured' 
_exptl_crystal_F_000             524 
_exptl_absorpt_coefficient_mu    0.075 
_exptl_absorpt_correction_type   empirical 
_exptl_absorpt_correction_T_min  1.000 
_exptl_absorpt_correction_T_max  1.000 
_exptl_absorpt_process_details   empirical 
  
_exptl_special_details 
; 
 ? 
; 
  
_diffrn_ambient_temperature      297(2) 
_diffrn_radiation_probe          x-ray 
_diffrn_radiation_type           MoK\a 
_diffrn_radiation_wavelength     0.71073 
_diffrn_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 ? 
_diffrn_standards_number         ? 
_diffrn_standards_interval_count ? 
_diffrn_standards_interval_time  ? 
_diffrn_standards_decay_%        ? 
_diffrn_reflns_number            8502 
_diffrn_reflns_av_R_equivalents  0.0244 
_diffrn_reflns_av_sigmaI/netI    0.0389 
_diffrn_reflns_limit_h_min       -11 
_diffrn_reflns_limit_h_max       11 
_diffrn_reflns_limit_k_min       -14 
_diffrn_reflns_limit_k_max       8 
_diffrn_reflns_limit_l_min       -17 
_diffrn_reflns_limit_l_max       16 
_diffrn_reflns_theta_min         2.25 
_diffrn_reflns_theta_max         26.12 
_reflns_number_total             5777 
_reflns_number_gt                3327 
_reflns_threshold_expression     >2sigma(I) 
  
_computing_data_collection       'Bruker SMART' 
_computing_cell_refinement       'Bruker SMART' 
_computing_data_reduction        'Bruker SHELXTL' 
_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)+(0.1500P)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    constro 
_refine_ls_extinction_method     none 
_refine_ls_extinction_coef       ? 
_refine_ls_number_reflns         5777 
_refine_ls_number_parameters     346 
_refine_ls_number_restraints     0 
_refine_ls_R_factor_all          0.1196 
_refine_ls_R_factor_gt           0.0778 
_refine_ls_wR_factor_ref         0.2627 
_refine_ls_wR_factor_gt          0.2280 
_refine_ls_goodness_of_fit_ref   1.122 
_refine_ls_restrained_S_all      1.122 
_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 
N N 0.2259(3) 0.3769(3) 0.46786(19) 0.0747(8) Uani 1 1 d . . . 
O1 O 0.56736(19) 0.26957(15) 0.09137(13) 0.0499(5) Uani 1 1 d . . . 
O2 O 0.6518(2) 0.41510(19) 0.31165(14) 0.0657(6) Uani 1 1 d . . . 
O3 O 0.8519(3) 0.4386(2) 0.25001(18) 0.0818(7) Uani 1 1 d . . . 
O4 O 0.7573(2) -0.02238(17) 0.00058(15) 0.0648(6) Uani 1 1 d . . . 
O5 O 0.4118(3) 0.1319(2) -0.28558(19) 0.0968(9) Uani 1 1 d . . . 
C1 C 0.6006(3) 0.3220(2) 0.15859(19) 0.0452(6) Uani 1 1 d . . . 
C2 C 0.4991(3) 0.3350(2) 0.23414(19) 0.0479(6) Uani 1 1 d . . . 
C3 C 0.3717(3) 0.3035(2) 0.2390(2) 0.0546(7) Uani 1 1 d . . . 
H3A H 0.3469 0.2730 0.1890 0.066 Uiso 1 1 calc R . . 
C4 C 0.2827(3) 0.3159(3) 0.3148(2) 0.0604(8) Uani 1 1 d . . . 
H4A H 0.1991 0.2935 0.3156 0.073 Uiso 1 1 calc R . . 
C5 C 0.3159(4) 0.3625(3) 0.3922(2) 0.0578(8) Uani 1 1 d . . . 
C6 C 0.4414(4) 0.3948(3) 0.3879(2) 0.0609(8) Uani 1 1 d . . . 
H6A H 0.4665 0.4256 0.4375 0.073 Uiso 1 1 calc R . . 
C7 C 0.5293(3) 0.3814(2) 0.3103(2) 0.0527(7) Uani 1 1 d . . . 
C8 C 0.7489(4) 0.4061(3) 0.2382(2) 0.0591(7) Uani 1 1 d . . . 
C9 C 0.7208(3) 0.3596(2) 0.15677(19) 0.0486(6) Uani 1 1 d . . . 
C10 C 0.8195(3) 0.3587(2) 0.0727(2) 0.0527(7) Uani 1 1 d . . . 
C11 C 0.7588(3) 0.3136(2) -0.0070(2) 0.0537(7) Uani 1 1 d . . . 
H11A H 0.6854 0.3823 -0.0517 0.064 Uiso 1 1 calc R . . 
H11B H 0.8391 0.2816 -0.0457 0.064 Uiso 1 1 calc R . . 
C12 C 0.6898(3) 0.2178(2) 0.03200(19) 0.0485(7) Uani 1 1 d . . . 
C13 C 0.7904(3) 0.1035(2) 0.0979(2) 0.0522(7) Uani 1 1 d . . . 
H13A H 0.8357 0.1077 0.1552 0.063 Uiso 1 1 calc R . . 
C14 C 0.8208(3) -0.0054(2) 0.0808(2) 0.0521(7) Uani 1 1 d . . . 
C15 C 0.6514(3) 0.0765(3) -0.0617(2) 0.0528(7) Uani 1 1 d . . . 
C16 C 0.6153(3) 0.1909(2) -0.04997(19) 0.0498(7) Uani 1 1 d . . . 
C17 C 0.5093(3) 0.2826(3) -0.1195(2) 0.0618(8) Uani 1 1 d . . . 
H17A H 0.4830 0.3615 -0.1141 0.074 Uiso 1 1 calc R . . 
C18 C 0.4422(4) 0.2596(3) -0.1962(2) 0.0674(9) Uani 1 1 d . . . 
H18A H 0.3697 0.3219 -0.2406 0.081 Uiso 1 1 calc R . . 
C19 C 0.4835(4) 0.1439(3) -0.2061(2) 0.0661(8) Uani 1 1 d . . . 
C20 C 0.5867(4) 0.0514(3) -0.1394(2) 0.0666(9) Uani 1 1 d . . . 
H20A H 0.6134 -0.0272 -0.1457 0.080 Uiso 1 1 calc R . . 
C21 C 0.1119(5) 0.3266(5) 0.4825(3) 0.1078(14) Uani 1 1 d . . . 
H21A H 0.0975 0.2988 0.4257 0.162 Uiso 1 1 calc R . . 
H21B H 0.0219 0.3870 0.4908 0.162 Uiso 1 1 calc R . . 
H21C H 0.1388 0.2600 0.5409 0.162 Uiso 1 1 calc R . . 
C22 C 0.2643(7) 0.4243(7) 0.5456(4) 0.0984(15) Uani 1 1 d . . . 
C23 C 0.8119(4) 0.4890(3) 0.0224(2) 0.0670(9) Uani 1 1 d . . . 
H23A H 0.8481 0.5210 0.0696 0.101 Uiso 1 1 calc R . . 
H23B H 0.7114 0.5382 -0.0007 0.101 Uiso 1 1 calc R . . 
H23C H 0.8716 0.4888 -0.0329 0.101 Uiso 1 1 calc R . . 
C24 C 0.9832(3) 0.2823(3) 0.1076(3) 0.0701(9) Uani 1 1 d . . . 
H24A H 0.9910 0.2006 0.1391 0.105 Uiso 1 1 calc R . . 
H24B H 1.0193 0.3153 0.1540 0.105 Uiso 1 1 calc R . . 
H24C H 1.0408 0.2836 0.0512 0.105 Uiso 1 1 calc R . . 
C25 C 0.9240(3) -0.1187(2) 0.1431(2) 0.0551(7) Uani 1 1 d . . . 
C26 C 0.8984(4) -0.2266(3) 0.1539(2) 0.0664(8) Uani 1 1 d . . . 
H26A H 0.8163 -0.2273 0.1194 0.080 Uiso 1 1 calc R . . 
C27 C 0.9923(5) -0.3323(3) 0.2148(3) 0.0804(11) Uani 1 1 d . . . 
H27A H 0.9744 -0.4043 0.2215 0.096 Uiso 1 1 calc R . . 
C28 C 1.1134(5) -0.3304(3) 0.2659(3) 0.0896(12) Uani 1 1 d . . . 
H28A H 1.1763 -0.4016 0.3080 0.108 Uiso 1 1 calc R . . 
C29 C 1.1434(4) -0.2253(3) 0.2560(3) 0.0833(11) Uani 1 1 d . . . 
H29A H 1.2262 -0.2253 0.2903 0.100 Uiso 1 1 calc R . . 
C30 C 1.0478(4) -0.1193(3) 0.1940(2) 0.0676(9) Uani 1 1 d . . . 
H30A H 1.0670 -0.0477 0.1865 0.081 Uiso 1 1 calc R . . 
C31 C 0.4454(6) 0.0126(4) -0.2977(3) 0.1161(16) Uani 1 1 d . . . 
H31A H 0.3889 0.0156 -0.3556 0.174 Uiso 1 1 calc R . . 
H31B H 0.4210 -0.0374 -0.2401 0.174 Uiso 1 1 calc R . . 
H31C H 0.5489 -0.0206 -0.3055 0.174 Uiso 1 1 calc R . . 
H22A H 0.183(4) 0.426(3) 0.593(3) 0.095(11) Uiso 1 1 d . . . 
H22B H 0.336(6) 0.365(5) 0.585(4) 0.15(2) Uiso 1 1 d . . . 
H22C H 0.252(6) 0.500(5) 0.516(4) 0.14(2) 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 
N C5 1.370(4) . ? 
N C21 1.416(5) . ? 
N C22 1.445(5) . ? 
O1 C1 1.347(3) . ? 
O1 C12 1.493(3) . ? 
O2 C7 1.373(3) . ? 
O2 C8 1.384(4) . ? 
O3 C8 1.209(4) . ? 
O4 C14 1.365(3) . ? 
O4 C15 1.384(3) . ? 
O5 C19 1.368(4) . ? 
O5 C31 1.432(4) . ? 
C1 C9 1.376(4) . ? 
C1 C2 1.436(4) . ? 
C2 C7 1.391(4) . ? 
C2 C3 1.398(4) . ? 
C3 C4 1.363(4) . ? 
C3 H3A 0.9300 . ? 
C4 C5 1.418(4) . ? 
C4 H4A 0.9300 . ? 
C5 C6 1.386(4) . ? 
C6 C7 1.378(4) . ? 
C6 H6A 0.9300 . ? 
C8 C9 1.448(4) . ? 
C9 C10 1.507(4) . ? 
C10 C23 1.544(4) . ? 
C10 C11 1.545(4) . ? 
C10 C24 1.547(4) . ? 
C11 C12 1.514(4) . ? 
C11 H11A 0.9700 . ? 
C11 H11B 0.9700 . ? 
C12 C13 1.482(4) . ? 
C12 C16 1.506(4) . ? 
C13 C14 1.341(4) . ? 
C13 H13A 0.9300 . ? 
C14 C25 1.465(4) . ? 
C15 C16 1.369(4) . ? 
C15 C20 1.395(4) . ? 
C16 C17 1.393(4) . ? 
C17 C18 1.380(4) . ? 
C17 H17A 0.9300 . ? 
C18 C19 1.372(4) . ? 
C18 H18A 0.9300 . ? 
C19 C20 1.365(4) . ? 
C20 H20A 0.9300 . ? 
C21 H21A 0.9600 . ? 
C21 H21B 0.9600 . ? 
C21 H21C 0.9600 . ? 
C22 H22A 1.02(4) . ? 
C22 H22B 0.88(6) . ? 
C22 H22C 0.88(5) . ? 
C23 H23A 0.9600 . ? 
C23 H23B 0.9600 . ? 
C23 H23C 0.9600 . ? 
C24 H24A 0.9600 . ? 
C24 H24B 0.9600 . ? 
C24 H24C 0.9600 . ? 
C25 C30 1.385(4) . ? 
C25 C26 1.386(4) . ? 
C26 C27 1.374(5) . ? 
C26 H26A 0.9300 . ? 
C27 C28 1.377(6) . ? 
C27 H27A 0.9300 . ? 
C28 C29 1.376(6) . ? 
C28 H28A 0.9300 . ? 
C29 C30 1.387(4) . ? 
C29 H29A 0.9300 . ? 
C30 H30A 0.9300 . ? 
C31 H31A 0.9600 . ? 
C31 H31B 0.9600 . ? 
C31 H31C 0.9600 . ? 
  
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 
C5 N C21 121.6(3) . . ? 
C5 N C22 119.4(3) . . ? 
C21 N C22 117.9(3) . . ? 
C1 O1 C12 116.2(2) . . ? 
C7 O2 C8 122.4(2) . . ? 
C14 O4 C15 118.0(2) . . ? 
C19 O5 C31 117.1(3) . . ? 
O1 C1 C9 123.9(2) . . ? 
O1 C1 C2 113.9(2) . . ? 
C9 C1 C2 122.2(2) . . ? 
C7 C2 C3 116.3(2) . . ? 
C7 C2 C1 118.1(3) . . ? 
C3 C2 C1 125.7(2) . . ? 
C4 C3 C2 122.1(3) . . ? 
C4 C3 H3A 118.9 . . ? 
C2 C3 H3A 118.9 . . ? 
C3 C4 C5 120.8(3) . . ? 
C3 C4 H4A 119.6 . . ? 
C5 C4 H4A 119.6 . . ? 
N C5 C6 121.1(3) . . ? 
N C5 C4 121.2(3) . . ? 
C6 C5 C4 117.6(3) . . ? 
C7 C6 C5 120.3(3) . . ? 
C7 C6 H6A 119.9 . . ? 
C5 C6 H6A 119.9 . . ? 
O2 C7 C6 116.7(2) . . ? 
O2 C7 C2 120.4(2) . . ? 
C6 C7 C2 122.9(3) . . ? 
O3 C8 O2 114.6(3) . . ? 
O3 C8 C9 126.3(3) . . ? 
O2 C8 C9 119.1(3) . . ? 
C1 C9 C8 117.7(3) . . ? 
C1 C9 C10 123.0(2) . . ? 
C8 C9 C10 119.2(2) . . ? 
C9 C10 C23 109.5(2) . . ? 
C9 C10 C11 108.5(2) . . ? 
C23 C10 C11 106.6(2) . . ? 
C9 C10 C24 112.8(2) . . ? 
C23 C10 C24 107.8(3) . . ? 
C11 C10 C24 111.4(2) . . ? 
C12 C11 C10 115.8(2) . . ? 
C12 C11 H11A 108.3 . . ? 
C10 C11 H11A 108.3 . . ? 
C12 C11 H11B 108.3 . . ? 
C10 C11 H11B 108.3 . . ? 
H11A C11 H11B 107.4 . . ? 
C13 C12 O1 107.2(2) . . ? 
C13 C12 C16 109.7(2) . . ? 
O1 C12 C16 104.6(2) . . ? 
C13 C12 C11 115.2(2) . . ? 
O1 C12 C11 107.0(2) . . ? 
C16 C12 C11 112.5(2) . . ? 
C14 C13 C12 124.6(3) . . ? 
C14 C13 H13A 117.7 . . ? 
C12 C13 H13A 117.7 . . ? 
C13 C14 O4 122.6(3) . . ? 
C13 C14 C25 125.4(3) . . ? 
O4 C14 C25 112.0(2) . . ? 
C16 C15 O4 122.9(2) . . ? 
C16 C15 C20 122.3(3) . . ? 
O4 C15 C20 114.8(3) . . ? 
C15 C16 C17 116.9(3) . . ? 
C15 C16 C12 121.9(2) . . ? 
C17 C16 C12 121.2(2) . . ? 
C18 C17 C16 121.9(3) . . ? 
C18 C17 H17A 119.1 . . ? 
C16 C17 H17A 119.1 . . ? 
C19 C18 C17 119.3(3) . . ? 
C19 C18 H18A 120.3 . . ? 
C17 C18 H18A 120.3 . . ? 
C20 C19 O5 125.0(3) . . ? 
C20 C19 C18 120.7(3) . . ? 
O5 C19 C18 114.3(3) . . ? 
C19 C20 C15 119.0(3) . . ? 
C19 C20 H20A 120.5 . . ? 
C15 C20 H20A 120.5 . . ? 
N C21 H21A 109.5 . . ? 
N C21 H21B 109.5 . . ? 
H21A C21 H21B 109.5 . . ? 
N C21 H21C 109.5 . . ? 
H21A C21 H21C 109.5 . . ? 
H21B C21 H21C 109.5 . . ? 
N C22 H22A 105(2) . . ? 
N C22 H22B 107(4) . . ? 
H22A C22 H22B 98(4) . . ? 
N C22 H22C 105(3) . . ? 
H22A C22 H22C 106(4) . . ? 
H22B C22 H22C 134(5) . . ? 
C10 C23 H23A 109.5 . . ? 
C10 C23 H23B 109.5 . . ? 
H23A C23 H23B 109.5 . . ? 
C10 C23 H23C 109.5 . . ? 
H23A C23 H23C 109.5 . . ? 
H23B C23 H23C 109.5 . . ? 
C10 C24 H24A 109.5 . . ? 
C10 C24 H24B 109.5 . . ? 
H24A C24 H24B 109.5 . . ? 
C10 C24 H24C 109.5 . . ? 
H24A C24 H24C 109.5 . . ? 
H24B C24 H24C 109.5 . . ? 
C30 C25 C26 118.8(3) . . ? 
C30 C25 C14 120.3(3) . . ? 
C26 C25 C14 120.9(3) . . ? 
C27 C26 C25 121.0(3) . . ? 
C27 C26 H26A 119.5 . . ? 
C25 C26 H26A 119.5 . . ? 
C26 C27 C28 119.2(3) . . ? 
C26 C27 H27A 120.4 . . ? 
C28 C27 H27A 120.4 . . ? 
C29 C28 C27 121.4(3) . . ? 
C29 C28 H28A 119.3 . . ? 
C27 C28 H28A 119.3 . . ? 
C28 C29 C30 118.7(4) . . ? 
C28 C29 H29A 120.6 . . ? 
C30 C29 H29A 120.6 . . ? 
C25 C30 C29 120.9(3) . . ? 
C25 C30 H30A 119.6 . . ? 
C29 C30 H30A 119.6 . . ? 
O5 C31 H31A 109.5 . . ? 
O5 C31 H31B 109.5 . . ? 
H31A C31 H31B 109.5 . . ? 
O5 C31 H31C 109.5 . . ? 
H31A C31 H31C 109.5 . . ? 
H31B C31 H31C 109.5 . . ? 
  
_diffrn_measured_fraction_theta_max 0.978 
_diffrn_reflns_theta_full        26.12 
_diffrn_measured_fraction_theta_full 0.978 
_refine_diff_density_max         0.871 
_refine_diff_density_min         -0.344 
_refine_diff_density_rms         0.104 
  
  
