 
data_n00024 
 
_audit_creation_method            SHELXL-97 
_chemical_name_systematic 
; 
 ? 
; 
_chemical_name_common             ? 
_chemical_melting_point           ? 
_chemical_formula_moiety          ? 
_chemical_formula_sum 
 'C28 H32 N2 O3' 
_chemical_formula_weight          444.56 
 
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    P2(1)/c 
 
loop_ 
 _symmetry_equiv_pos_as_xyz 
 'x, y, z' 
 '-x, y+1/2, -z+1/2' 
 '-x, -y, -z' 
 'x, -y-1/2, z-1/2' 
 
_cell_length_a                    9.3178(11) 
_cell_length_b                    26.180(3) 
_cell_length_c                    9.0683(10) 
_cell_angle_alpha                 90.00 
_cell_angle_beta                  90.272(2) 
_cell_angle_gamma                 90.00 
_cell_volume                      2212.1(4) 
_cell_formula_units_Z             4 
_cell_measurement_temperature     133(2) 
_cell_measurement_reflns_used     15328 
_cell_measurement_theta_min       2.32 
_cell_measurement_theta_max       28.27 
 
_exptl_crystal_description        prism 
_exptl_crystal_colour             colorless 
_exptl_crystal_size_max           0.40 
_exptl_crystal_size_mid           0.38 
_exptl_crystal_size_min           0.32 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_diffrn     1.335 
_exptl_crystal_density_method     'not measured' 
_exptl_crystal_F_000              952 
_exptl_absorpt_coefficient_mu     0.087 
_exptl_absorpt_correction_type    empirical 
_exptl_absorpt_correction_T_min   0.9662 
_exptl_absorpt_correction_T_max   0.9728 
_exptl_absorpt_process_details    ? 
 
_exptl_special_details 
; 
 ? 
; 
 
_diffrn_ambient_temperature       133(2) 
_diffrn_radiation_wavelength      0.71073 
_diffrn_radiation_type            MoK\a 
_diffrn_radiation_source          'normal-focus sealed tube' 
_diffrn_radiation_monochromator   graphite 
_diffrn_measurement_device_type   Platform 
_diffrn_measurement_method        'ω scan frames' 
_diffrn_detector_area_resol_mean  ? 
_diffrn_standards_number          180 
_diffrn_standards_interval_count  ? 
_diffrn_standards_interval_time   ? 
_diffrn_standards_decay_%         0.8 
_diffrn_reflns_number             15394 
_diffrn_reflns_av_R_equivalents   0.0528 
_diffrn_reflns_av_sigmaI/netI     0.0562 
_diffrn_reflns_limit_h_min        -12 
_diffrn_reflns_limit_h_max        11 
_diffrn_reflns_limit_k_min        -34 
_diffrn_reflns_limit_k_max        20 
_diffrn_reflns_limit_l_min        -12 
_diffrn_reflns_limit_l_max        11 
_diffrn_reflns_theta_min          2.19 
_diffrn_reflns_theta_max          28.29 
_reflns_number_total              5460 
_reflns_number_gt                 3890 
_reflns_threshold_expression      >2sigma(I) 
 
_computing_data_collection        ? 
_computing_cell_refinement        ? 
_computing_data_reduction         ? 
_computing_structure_solution     'SHELXS-97 (Sheldrick, 1990)' 
_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)+(0.0771P)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          5460 
_refine_ls_number_parameters      299 
_refine_ls_number_restraints      0 
_refine_ls_R_factor_all           0.0790 
_refine_ls_R_factor_gt            0.0534 
_refine_ls_wR_factor_ref          0.1450 
_refine_ls_wR_factor_gt           0.1318 
_refine_ls_goodness_of_fit_ref    1.050 
_refine_ls_restrained_S_all       1.050 
_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 0.76284(14) 0.55787(5) 0.32593(14) 0.0219(3) Uani 1 1 d . . . 
N2 N 0.20268(15) 0.69391(5) 1.17400(15) 0.0232(3) Uani 1 1 d . . . 
O1 O 0.70685(13) 0.67531(5) 0.84121(14) 0.0325(3) Uani 1 1 d . . . 
O2 O 0.82732(15) 0.47079(5) -0.04223(15) 0.0393(4) Uani 1 1 d . . . 
O3 O 0.15493(15) 0.62829(6) 1.58191(16) 0.0452(4) Uani 1 1 d . . . 
C1 C 0.81508(18) 0.49782(7) 0.06643(19) 0.0285(4) Uani 1 1 d . . . 
C2 C 0.87405(19) 0.48229(7) 0.21456(19) 0.0278(4) Uani 1 1 d . . . 
H2A H 0.9738 0.4950 0.2236 0.033 Uiso 1 1 calc R . . 
H2B H 0.8773 0.4445 0.2196 0.033 Uiso 1 1 calc R . . 
C3 C 0.78698(17) 0.50229(7) 0.34542(18) 0.0233(4) Uani 1 1 d . . . 
H3 H 0.8461 0.4974 0.4367 0.028 Uiso 1 1 calc R . . 
C4 C 0.64493(19) 0.47408(7) 0.3670(2) 0.0288(4) Uani 1 1 d . . . 
H4A H 0.6638 0.4369 0.3732 0.035 Uiso 1 1 calc R . . 
H4B H 0.6017 0.4850 0.4615 0.035 Uiso 1 1 calc R . . 
C5 C 0.53838(19) 0.48424(7) 0.2417(2) 0.0299(4) Uani 1 1 d . . . 
H5A H 0.5722 0.4673 0.1507 0.036 Uiso 1 1 calc R . . 
H5B H 0.4438 0.4696 0.2675 0.036 Uiso 1 1 calc R . . 
C6 C 0.52278(18) 0.54130(7) 0.21407(19) 0.0280(4) Uani 1 1 d . . . 
H6A H 0.4707 0.5571 0.2974 0.034 Uiso 1 1 calc R . . 
H6B H 0.4653 0.5468 0.1234 0.034 Uiso 1 1 calc R . . 
C7 C 0.66894(18) 0.56739(7) 0.19716(17) 0.0240(4) Uani 1 1 d . . . 
H7A H 0.6523 0.6050 0.1900 0.029 Uiso 1 1 calc R . . 
C8 C 0.74984(19) 0.55041(7) 0.05825(18) 0.0285(4) Uani 1 1 d . . . 
H8A H 0.6826 0.5515 -0.0265 0.034 Uiso 1 1 calc R . . 
H8B H 0.8273 0.5754 0.0386 0.034 Uiso 1 1 calc R . . 
C9 C 0.74135(17) 0.58730(6) 0.45483(17) 0.0212(3) Uani 1 1 d . . . 
C10 C 0.63928(18) 0.62623(7) 0.46477(19) 0.0261(4) Uani 1 1 d . . . 
H10 H 0.5775 0.6328 0.3833 0.031 Uiso 1 1 calc R . . 
C11 C 0.62650(19) 0.65554(7) 0.5918(2) 0.0285(4) Uani 1 1 d . . . 
H11 H 0.5575 0.6822 0.5955 0.034 Uiso 1 1 calc R . . 
C12 C 0.71313(18) 0.64622(7) 0.71264(18) 0.0254(4) Uani 1 1 d . . . 
C13 C 0.81767(18) 0.60907(7) 0.70324(18) 0.0273(4) Uani 1 1 d . . . 
H13 H 0.8802 0.6033 0.7846 0.033 Uiso 1 1 calc R . . 
C14 C 0.83213(18) 0.58033(7) 0.57706(18) 0.0260(4) Uani 1 1 d . . . 
H14 H 0.9054 0.5552 0.5726 0.031 Uiso 1 1 calc R . . 
C15 C 0.58042(17) 0.67599(7) 0.92188(18) 0.0238(4) Uani 1 1 d . . . 
C16 C 0.45697(19) 0.64908(7) 0.8862(2) 0.0274(4) Uani 1 1 d . . . 
H16 H 0.4554 0.6274 0.8021 0.033 Uiso 1 1 calc R . . 
C17 C 0.33528(19) 0.65372(7) 0.97352(19) 0.0275(4) Uani 1 1 d . . . 
H17 H 0.2513 0.6352 0.9471 0.033 Uiso 1 1 calc R . . 
C18 C 0.33255(17) 0.68473(6) 1.09865(17) 0.0217(4) Uani 1 1 d . . . 
C19 C 0.46134(18) 0.70976(7) 1.13593(18) 0.0242(4) Uani 1 1 d . . . 
H19 H 0.4658 0.7297 1.2234 0.029 Uiso 1 1 calc R . . 
C20 C 0.58203(18) 0.70593(7) 1.04740(18) 0.0243(4) Uani 1 1 d . . . 
H20 H 0.6667 0.7241 1.0734 0.029 Uiso 1 1 calc R . . 
C21 C 0.17808(18) 0.64591(7) 1.4601(2) 0.0304(4) Uani 1 1 d . . . 
C22 C 0.1423(2) 0.61734(7) 1.3206(2) 0.0328(4) Uani 1 1 d . . . 
H22A H 0.0627 0.5934 1.3410 0.039 Uiso 1 1 calc R . . 
H22B H 0.2268 0.5968 1.2914 0.039 Uiso 1 1 calc R . . 
C23 C 0.09887(18) 0.65186(7) 1.19083(19) 0.0265(4) Uani 1 1 d . . . 
H23 H 0.1008 0.6308 1.0988 0.032 Uiso 1 1 calc R . . 
C24 C -0.05236(18) 0.67382(8) 1.2076(2) 0.0303(4) Uani 1 1 d . . . 
H24A H -0.0802 0.6913 1.1150 0.036 Uiso 1 1 calc R . . 
H24B H -0.1208 0.6455 1.2238 0.036 Uiso 1 1 calc R . . 
C25 C -0.06320(19) 0.71140(7) 1.3352(2) 0.0309(4) Uani 1 1 d . . . 
H25A H -0.0542 0.6929 1.4299 0.037 Uiso 1 1 calc R . . 
H25B H -0.1580 0.7284 1.3328 0.037 Uiso 1 1 calc R . . 
C26 C 0.05541(18) 0.75132(7) 1.3238(2) 0.0301(4) Uani 1 1 d . . . 
H26A H 0.0556 0.7726 1.4141 0.036 Uiso 1 1 calc R . . 
H26B H 0.0354 0.7739 1.2387 0.036 Uiso 1 1 calc R . . 
C27 C 0.20395(18) 0.72690(7) 1.30490(18) 0.0247(4) Uani 1 1 d . . . 
H27 H 0.2752 0.7549 1.2883 0.030 Uiso 1 1 calc R . . 
C28 C 0.2518(2) 0.69641(7) 1.44143(19) 0.0299(4) Uani 1 1 d . . . 
H28A H 0.3565 0.6904 1.4352 0.036 Uiso 1 1 calc R . . 
H28B H 0.2342 0.7174 1.5303 0.036 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 C9 1.415(2) . ? 
N1 C7 1.477(2) . ? 
N1 C3 1.483(2) . ? 
N2 C18 1.413(2) . ? 
N2 C27 1.468(2) . ? 
N2 C23 1.474(2) . ? 
O1 C15 1.390(2) . ? 
O1 C12 1.394(2) . ? 
O2 C1 1.219(2) . ? 
O3 C21 1.217(2) . ? 
C1 C2 1.505(3) . ? 
C1 C8 1.507(3) . ? 
C2 C3 1.533(2) . ? 
C3 C4 1.529(2) . ? 
C4 C5 1.529(2) . ? 
C5 C6 1.521(3) . ? 
C6 C7 1.532(2) . ? 
C7 C8 1.537(2) . ? 
C9 C10 1.397(2) . ? 
C9 C14 1.403(2) . ? 
C10 C11 1.390(2) . ? 
C11 C12 1.380(3) . ? 
C12 C13 1.380(2) . ? 
C13 C14 1.376(2) . ? 
C15 C20 1.382(2) . ? 
C15 C16 1.386(2) . ? 
C16 C17 1.391(2) . ? 
C17 C18 1.396(2) . ? 
C18 C19 1.407(2) . ? 
C19 C20 1.388(2) . ? 
C21 C28 1.500(3) . ? 
C21 C22 1.506(3) . ? 
C22 C23 1.536(3) . ? 
C23 C24 1.530(2) . ? 
C24 C25 1.523(3) . ? 
C25 C26 1.525(3) . ? 
C26 C27 1.535(2) . ? 
C27 C28 1.537(2) . ? 
 
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 C7 118.40(13) . . ? 
C9 N1 C3 117.25(13) . . ? 
C7 N1 C3 110.41(13) . . ? 
C18 N2 C27 119.17(13) . . ? 
C18 N2 C23 119.14(13) . . ? 
C27 N2 C23 111.01(13) . . ? 
C15 O1 C12 119.09(13) . . ? 
O2 C1 C2 121.98(18) . . ? 
O2 C1 C8 122.00(17) . . ? 
C2 C1 C8 115.87(15) . . ? 
C1 C2 C3 113.98(14) . . ? 
N1 C3 C4 110.99(13) . . ? 
N1 C3 C2 108.87(14) . . ? 
C4 C3 C2 113.33(15) . . ? 
C5 C4 C3 112.34(14) . . ? 
C6 C5 C4 110.77(15) . . ? 
C5 C6 C7 111.71(14) . . ? 
N1 C7 C6 111.67(13) . . ? 
N1 C7 C8 107.95(13) . . ? 
C6 C7 C8 113.13(14) . . ? 
C1 C8 C7 115.04(14) . . ? 
C10 C9 C14 116.87(15) . . ? 
C10 C9 N1 123.33(14) . . ? 
C14 C9 N1 119.65(15) . . ? 
C11 C10 C9 121.15(16) . . ? 
C12 C11 C10 120.56(16) . . ? 
C13 C12 C11 119.10(16) . . ? 
C13 C12 O1 117.99(15) . . ? 
C11 C12 O1 122.74(16) . . ? 
C14 C13 C12 120.57(16) . . ? 
C13 C14 C9 121.64(16) . . ? 
C20 C15 C16 119.10(15) . . ? 
C20 C15 O1 115.78(15) . . ? 
C16 C15 O1 125.12(15) . . ? 
C15 C16 C17 120.03(16) . . ? 
C16 C17 C18 122.11(16) . . ? 
C17 C18 C19 116.58(15) . . ? 
C17 C18 N2 120.73(15) . . ? 
C19 C18 N2 122.40(15) . . ? 
C20 C19 C18 121.30(15) . . ? 
C15 C20 C19 120.77(16) . . ? 
O3 C21 C28 121.33(18) . . ? 
O3 C21 C22 122.33(18) . . ? 
C28 C21 C22 116.26(15) . . ? 
C21 C22 C23 114.07(15) . . ? 
N2 C23 C24 109.56(15) . . ? 
N2 C23 C22 110.37(14) . . ? 
C24 C23 C22 112.59(14) . . ? 
C25 C24 C23 112.51(14) . . ? 
C24 C25 C26 109.93(14) . . ? 
C25 C26 C27 112.11(15) . . ? 
N2 C27 C26 109.37(14) . . ? 
N2 C27 C28 110.30(14) . . ? 
C26 C27 C28 112.61(14) . . ? 
C21 C28 C27 114.67(15) . . ? 
 
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 
O2 C1 C2 C3 -148.49(17) . . . . ? 
C8 C1 C2 C3 35.9(2) . . . . ? 
C9 N1 C3 C4 80.77(17) . . . . ? 
C7 N1 C3 C4 -58.90(17) . . . . ? 
C9 N1 C3 C2 -153.81(14) . . . . ? 
C7 N1 C3 C2 66.51(17) . . . . ? 
C1 C2 C3 N1 -49.9(2) . . . . ? 
C1 C2 C3 C4 74.2(2) . . . . ? 
N1 C3 C4 C5 55.18(19) . . . . ? 
C2 C3 C4 C5 -67.69(19) . . . . ? 
C3 C4 C5 C6 -50.69(19) . . . . ? 
C4 C5 C6 C7 50.40(19) . . . . ? 
C9 N1 C7 C6 -79.79(18) . . . . ? 
C3 N1 C7 C6 59.37(17) . . . . ? 
C9 N1 C7 C8 155.24(14) . . . . ? 
C3 N1 C7 C8 -65.60(16) . . . . ? 
C5 C6 C7 N1 -55.56(19) . . . . ? 
C5 C6 C7 C8 66.48(18) . . . . ? 
O2 C1 C8 C7 148.40(16) . . . . ? 
C2 C1 C8 C7 -36.0(2) . . . . ? 
N1 C7 C8 C1 49.41(19) . . . . ? 
C6 C7 C8 C1 -74.69(19) . . . . ? 
C7 N1 C9 C10 -2.5(2) . . . . ? 
C3 N1 C9 C10 -138.86(16) . . . . ? 
C7 N1 C9 C14 -177.80(15) . . . . ? 
C3 N1 C9 C14 45.8(2) . . . . ? 
C14 C9 C10 C11 -1.7(2) . . . . ? 
N1 C9 C10 C11 -177.17(16) . . . . ? 
C9 C10 C11 C12 -1.2(3) . . . . ? 
C10 C11 C12 C13 3.2(3) . . . . ? 
C10 C11 C12 O1 178.41(16) . . . . ? 
C15 O1 C12 C13 -122.44(17) . . . . ? 
C15 O1 C12 C11 62.3(2) . . . . ? 
C11 C12 C13 C14 -2.4(3) . . . . ? 
O1 C12 C13 C14 -177.80(16) . . . . ? 
C12 C13 C14 C9 -0.5(3) . . . . ? 
C10 C9 C14 C13 2.6(3) . . . . ? 
N1 C9 C14 C13 178.21(16) . . . . ? 
C12 O1 C15 C20 -179.59(15) . . . . ? 
C12 O1 C15 C16 0.9(3) . . . . ? 
C20 C15 C16 C17 2.1(3) . . . . ? 
O1 C15 C16 C17 -178.39(17) . . . . ? 
C15 C16 C17 C18 -0.4(3) . . . . ? 
C16 C17 C18 C19 -2.4(3) . . . . ? 
C16 C17 C18 N2 171.71(17) . . . . ? 
C27 N2 C18 C17 -179.77(15) . . . . ? 
C23 N2 C18 C17 38.9(2) . . . . ? 
C27 N2 C18 C19 -6.0(2) . . . . ? 
C23 N2 C18 C19 -147.42(16) . . . . ? 
C17 C18 C19 C20 3.6(3) . . . . ? 
N2 C18 C19 C20 -170.38(16) . . . . ? 
C16 C15 C20 C19 -0.9(3) . . . . ? 
O1 C15 C20 C19 179.55(16) . . . . ? 
C18 C19 C20 C15 -2.0(3) . . . . ? 
O3 C21 C22 C23 147.76(17) . . . . ? 
C28 C21 C22 C23 -35.5(2) . . . . ? 
C18 N2 C23 C24 -154.06(15) . . . . ? 
C27 N2 C23 C24 61.66(17) . . . . ? 
C18 N2 C23 C22 81.41(18) . . . . ? 
C27 N2 C23 C22 -62.86(17) . . . . ? 
C21 C22 C23 N2 48.36(19) . . . . ? 
C21 C22 C23 C24 -74.41(19) . . . . ? 
N2 C23 C24 C25 -56.04(19) . . . . ? 
C22 C23 C24 C25 67.2(2) . . . . ? 
C23 C24 C25 C26 50.9(2) . . . . ? 
C24 C25 C26 C27 -51.2(2) . . . . ? 
C18 N2 C27 C26 153.62(15) . . . . ? 
C23 N2 C27 C26 -62.12(18) . . . . ? 
C18 N2 C27 C28 -82.00(18) . . . . ? 
C23 N2 C27 C28 62.26(17) . . . . ? 
C25 C26 C27 N2 56.98(19) . . . . ? 
C25 C26 C27 C28 -66.04(19) . . . . ? 
O3 C21 C28 C27 -148.02(17) . . . . ? 
C22 C21 C28 C27 35.2(2) . . . . ? 
N2 C27 C28 C21 -47.69(19) . . . . ? 
C26 C27 C28 C21 74.81(19) . . . . ? 
 
_diffrn_measured_fraction_theta_max    0.993 
_diffrn_reflns_theta_full              25.00 
_diffrn_measured_fraction_theta_full   0.999 
_refine_diff_density_max    0.327 
_refine_diff_density_min   -0.216 
_refine_diff_density_rms    0.053 
