 
data_s92 
 
_audit_creation_method            SHELXL-97 
_chemical_name_systematic 
; 
 ? 
; 
_chemical_name_common             ? 
_chemical_formula_moiety          ? 
_chemical_formula_sum 
 'C23 H26 N2 O3' 
_chemical_formula_weight          378.46 
 
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)/n 
 
loop_ 
 _symmetry_equiv_pos_as_xyz 
 'x, y, z' 
 '-x+1/2, y+1/2, -z+1/2' 
 '-x, -y, -z' 
 'x-1/2, -y-1/2, z-1/2' 
 
_cell_length_a                    13.189(3) 
_cell_length_b                    9.300(2) 
_cell_length_c                    16.258(3) 
_cell_angle_alpha                 90.00 
_cell_angle_beta                  102.79(3) 
_cell_angle_gamma                 90.00 
_cell_volume                      1944.7(7) 
_cell_formula_units_Z             4 
_cell_measurement_temperature     150(2) 
_cell_measurement_reflns_used     ? 
_cell_measurement_theta_min       ? 
_cell_measurement_theta_max       ? 
 
_exptl_crystal_description        pyramid 
_exptl_crystal_colour             orange 
_exptl_crystal_size_max           0.20 
_exptl_crystal_size_mid           0.20 
_exptl_crystal_size_min           0.05 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_diffrn     1.293 
_exptl_crystal_density_method     'not measured' 
_exptl_crystal_F_000              808 
_exptl_absorpt_coefficient_mu     0.086 
_exptl_absorpt_correction_type    ? 
_exptl_absorpt_correction_T_min   0.9830 
_exptl_absorpt_correction_T_max   0.9957 
 
_exptl_special_details 
; 
 ? 
; 
 
_diffrn_ambient_temperature       150(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             11151 
_diffrn_reflns_av_R_equivalents   0.1000 
_diffrn_reflns_av_sigmaI/netI     0.0844 
_diffrn_reflns_limit_h_min        -15 
_diffrn_reflns_limit_h_max        15 
_diffrn_reflns_limit_k_min        -11 
_diffrn_reflns_limit_k_max        11 
_diffrn_reflns_limit_l_min        -19 
_diffrn_reflns_limit_l_max        19 
_diffrn_reflns_theta_min          2.57 
_diffrn_reflns_theta_max          25.25 
_reflns_number_total              3313 
_reflns_number_gt                 2165 
_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)+(0.0739P)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          3313 
_refine_ls_number_parameters      357 
_refine_ls_number_restraints      0 
_refine_ls_R_factor_all           0.0913 
_refine_ls_R_factor_gt            0.0491 
_refine_ls_wR_factor_ref          0.1324 
_refine_ls_wR_factor_gt           0.1124 
_refine_ls_goodness_of_fit_ref    0.961 
_refine_ls_restrained_S_all       0.961 
_refine_ls_shift/su_max           0.010 
_refine_ls_shift/su_mean          0.001 
 
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_calc_flag 
 _atom_site_refinement_flags 
 _atom_site_disorder_assembly 
 _atom_site_disorder_group 
O1 O 0.55180(11) -0.41986(18) -0.14008(11) 0.0490(5) Uani 1 d . . . 
O2 O 0.23422(11) -0.60495(15) -0.09069(9) 0.0319(4) Uani 1 d . . . 
H2O H 0.290(2) -0.557(4) -0.116(2) 0.108(12) Uiso 1 d . . . 
O3 O 0.18008(12) 0.23648(18) 0.19332(10) 0.0497(5) Uani 1 d . . . 
N1 N 0.33208(12) -0.45114(18) -0.19048(10) 0.0271(4) Uani 1 d . . . 
N2 N 0.22523(12) 0.01661(18) 0.08313(10) 0.0284(4) Uani 1 d . . . 
C1 C 0.50531(18) -0.5569(3) -0.16144(17) 0.0409(6) Uani 1 d . . . 
H1A H 0.4938(16) -0.603(2) -0.1085(15) 0.040(6) Uiso 1 d . . . 
H1B H 0.5553(19) -0.616(3) -0.1883(16) 0.055(7) Uiso 1 d . . . 
C2 C 0.40401(16) -0.5430(3) -0.22509(14) 0.0333(5) Uani 1 d . . . 
H2A H 0.4164(17) -0.496(2) -0.2797(14) 0.048(7) Uiso 1 d . . . 
H2B H 0.3730(16) -0.643(2) -0.2372(13) 0.040(6) Uiso 1 d . . . 
C3 C 0.38047(17) -0.3090(2) -0.16993(16) 0.0370(6) Uani 1 d . . . 
H3A H 0.3306(16) -0.248(2) -0.1444(12) 0.030(5) Uiso 1 d . . . 
H3B H 0.3919(15) -0.261(2) -0.2224(13) 0.033(6) Uiso 1 d . . . 
C4 C 0.48306(19) -0.3281(3) -0.10772(17) 0.0453(6) Uani 1 d . . . 
H4A H 0.5224(17) -0.230(3) -0.0921(13) 0.044(6) Uiso 1 d . . . 
H4B H 0.4719(18) -0.373(3) -0.0548(16) 0.054(7) Uiso 1 d . . . 
C5 C 0.22884(15) -0.4420(2) -0.24626(12) 0.0266(5) Uani 1 d . . . 
C6 C 0.21778(17) -0.4103(2) -0.33124(13) 0.0321(5) Uani 1 d . . . 
H6 H 0.2814(16) -0.390(2) -0.3553(13) 0.038(6) Uiso 1 d . . . 
C7 C 0.12038(18) -0.4079(3) -0.38486(15) 0.0385(6) Uani 1 d . . . 
H7 H 0.1136(15) -0.390(2) -0.4432(14) 0.037(6) Uiso 1 d . . . 
C8 C 0.03320(18) -0.4338(2) -0.35318(14) 0.0348(6) Uani 1 d . . . 
H8 H -0.0366(16) -0.441(2) -0.3904(12) 0.029(5) Uiso 1 d . . . 
C9 C 0.04401(17) -0.4622(2) -0.26846(14) 0.0312(5) Uani 1 d . . . 
H9 H -0.0131(17) -0.479(2) -0.2452(13) 0.039(6) Uiso 1 d . . . 
C10 C 0.14149(15) -0.4683(2) -0.21289(12) 0.0259(5) Uani 1 d . . . 
C11 C 0.15255(15) -0.5023(2) -0.11870(12) 0.0273(5) Uani 1 d . . . 
C12 C 0.05732(17) -0.5715(2) -0.10352(13) 0.0315(5) Uani 1 d . . . 
C13 C -0.01733(19) -0.6273(3) -0.08903(15) 0.0399(6) Uani 1 d . . . 
H13 H -0.0782(18) -0.671(2) -0.0782(14) 0.045(7) Uiso 1 d . . . 
C14 C 0.17281(15) -0.3629(2) -0.06613(12) 0.0246(5) Uani 1 d . . . 
C15 C 0.24995(16) -0.3560(2) 0.00764(13) 0.0279(5) Uani 1 d . . . 
H15 H 0.2897(15) -0.436(2) 0.0248(12) 0.028(6) Uiso 1 d . . . 
C16 C 0.26617(15) -0.2315(2) 0.05554(13) 0.0276(5) Uani 1 d . . . 
H16 H 0.3189(15) -0.229(2) 0.1081(12) 0.027(5) Uiso 1 d . . . 
C17 C 0.20660(14) -0.1085(2) 0.03177(12) 0.0247(5) Uani 1 d . . . 
C18 C 0.13000(16) -0.1154(2) -0.04269(12) 0.0259(5) Uani 1 d . . . 
H18 H 0.0850(16) -0.034(2) -0.0622(12) 0.036(6) Uiso 1 d . . . 
C19 C 0.11380(16) -0.2413(2) -0.08999(13) 0.0262(5) Uani 1 d . . . 
H19 H 0.0572(16) -0.245(2) -0.1394(13) 0.034(6) Uiso 1 d . . . 
C20 C 0.2227(2) -0.0120(3) 0.17159(14) 0.0407(6) Uani 1 d . . . 
H20A H 0.2751(18) -0.086(3) 0.1945(15) 0.051(7) Uiso 1 d . . . 
H20B H 0.1493(18) -0.044(2) 0.1772(13) 0.039(6) Uiso 1 d . . . 
C21 C 0.2493(2) 0.1219(3) 0.22375(18) 0.0521(7) Uani 1 d . . . 
H21A H 0.2414(18) 0.102(3) 0.2809(17) 0.054(7) Uiso 1 d . . . 
H21B H 0.3242(19) 0.153(3) 0.2223(14) 0.053(7) Uiso 1 d . . . 
C22 C 0.1904(2) 0.2698(3) 0.10905(16) 0.0420(6) Uani 1 d . . . 
H22A H 0.2648(18) 0.300(2) 0.1119(13) 0.047(6) Uiso 1 d . . . 
H22B H 0.1420(19) 0.348(3) 0.0867(15) 0.057(8) Uiso 1 d . . . 
C23 C 0.16200(17) 0.1425(2) 0.05125(14) 0.0317(5) Uani 1 d . . . 
H23A H 0.0913(17) 0.121(2) 0.0462(12) 0.029(6) Uiso 1 d . . . 
H23B H 0.1733(15) 0.172(2) -0.0074(14) 0.035(6) Uiso 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 C1 1.424(3) . ? 
O1 C4 1.428(3) . ? 
O2 C11 1.436(2) . ? 
O2 H2O 1.02(3) . ? 
O3 C21 1.420(3) . ? 
O3 C22 1.440(3) . ? 
N1 C5 1.462(2) . ? 
N1 C3 1.474(3) . ? 
N1 C2 1.477(3) . ? 
N1 H2O 1.74(3) . ? 
N2 C17 1.421(3) . ? 
N2 C23 1.464(3) . ? 
N2 C20 1.471(3) . ? 
C1 C2 1.504(3) . ? 
C1 H1A 1.00(2) . ? 
C1 H1B 1.03(3) . ? 
C2 H2A 1.04(2) . ? 
C2 H2B 1.02(2) . ? 
C3 C4 1.510(3) . ? 
C3 H3A 1.03(2) . ? 
C3 H3B 1.01(2) . ? 
C4 H4A 1.05(2) . ? 
C4 H4B 1.00(2) . ? 
C5 C6 1.388(3) . ? 
C5 C10 1.399(3) . ? 
C6 C7 1.384(3) . ? 
C6 H6 1.02(2) . ? 
C7 C8 1.381(3) . ? 
C7 H7 0.95(2) . ? 
C8 C9 1.378(3) . ? 
C8 H8 0.99(2) . ? 
C9 C10 1.399(3) . ? 
C9 H9 0.93(2) . ? 
C10 C11 1.539(3) . ? 
C11 C12 1.480(3) . ? 
C11 C14 1.543(3) . ? 
C12 C13 1.182(3) . ? 
C13 H13 0.95(2) . ? 
C14 C19 1.379(3) . ? 
C14 C15 1.392(3) . ? 
C15 C16 1.386(3) . ? 
C15 H15 0.92(2) . ? 
C16 C17 1.393(3) . ? 
C16 H16 0.976(19) . ? 
C17 C18 1.396(3) . ? 
C18 C19 1.391(3) . ? 
C18 H18 0.97(2) . ? 
C19 H19 0.97(2) . ? 
C20 C21 1.504(3) . ? 
C20 H20A 0.99(2) . ? 
C20 H20B 1.03(2) . ? 
C21 H21A 0.98(3) . ? 
C21 H21B 1.03(2) . ? 
C22 C23 1.507(3) . ? 
C22 H22A 1.01(2) . ? 
C22 H22B 0.98(3) . ? 
C23 H23A 0.94(2) . ? 
C23 H23B 1.04(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 
C1 O1 C4 110.54(18) . . ? 
C11 O2 H2O 97.8(18) . . ? 
C21 O3 C22 107.7(2) . . ? 
C5 N1 C3 112.67(16) . . ? 
C5 N1 C2 112.70(16) . . ? 
C3 N1 C2 108.81(16) . . ? 
C5 N1 H2O 93.8(10) . . ? 
C3 N1 H2O 122.5(11) . . ? 
C2 N1 H2O 105.6(10) . . ? 
C17 N2 C23 115.83(16) . . ? 
C17 N2 C20 112.83(16) . . ? 
C23 N2 C20 110.88(18) . . ? 
O1 C1 C2 111.09(19) . . ? 
O1 C1 H1A 108.3(13) . . ? 
C2 C1 H1A 110.3(12) . . ? 
O1 C1 H1B 107.5(13) . . ? 
C2 C1 H1B 108.1(14) . . ? 
H1A C1 H1B 111.6(19) . . ? 
N1 C2 C1 109.60(19) . . ? 
N1 C2 H2A 108.5(12) . . ? 
C1 C2 H2A 110.0(12) . . ? 
N1 C2 H2B 109.7(12) . . ? 
C1 C2 H2B 108.1(12) . . ? 
H2A C2 H2B 110.9(18) . . ? 
N1 C3 C4 109.00(19) . . ? 
N1 C3 H3A 107.9(11) . . ? 
C4 C3 H3A 110.8(11) . . ? 
N1 C3 H3B 110.4(12) . . ? 
C4 C3 H3B 109.9(11) . . ? 
H3A C3 H3B 108.8(16) . . ? 
O1 C4 C3 111.8(2) . . ? 
O1 C4 H4A 106.8(12) . . ? 
C3 C4 H4A 112.3(12) . . ? 
O1 C4 H4B 107.1(13) . . ? 
C3 C4 H4B 110.3(14) . . ? 
H4A C4 H4B 108.3(18) . . ? 
C6 C5 C10 120.58(19) . . ? 
C6 C5 N1 120.53(18) . . ? 
C10 C5 N1 118.88(18) . . ? 
C7 C6 C5 120.6(2) . . ? 
C7 C6 H6 118.9(12) . . ? 
C5 C6 H6 120.5(12) . . ? 
C8 C7 C6 119.7(2) . . ? 
C8 C7 H7 120.2(12) . . ? 
C6 C7 H7 120.1(12) . . ? 
C9 C8 C7 119.7(2) . . ? 
C9 C8 H8 118.5(11) . . ? 
C7 C8 H8 121.6(11) . . ? 
C8 C9 C10 122.0(2) . . ? 
C8 C9 H9 121.7(13) . . ? 
C10 C9 H9 116.3(13) . . ? 
C5 C10 C9 117.39(19) . . ? 
C5 C10 C11 121.14(17) . . ? 
C9 C10 C11 121.47(18) . . ? 
O2 C11 C12 105.23(16) . . ? 
O2 C11 C10 110.57(15) . . ? 
C12 C11 C10 111.00(16) . . ? 
O2 C11 C14 110.92(16) . . ? 
C12 C11 C14 108.80(16) . . ? 
C10 C11 C14 110.21(16) . . ? 
C13 C12 C11 178.1(2) . . ? 
C12 C13 H13 178.9(13) . . ? 
C19 C14 C15 117.65(19) . . ? 
C19 C14 C11 121.02(17) . . ? 
C15 C14 C11 121.32(18) . . ? 
C16 C15 C14 121.0(2) . . ? 
C16 C15 H15 120.0(12) . . ? 
C14 C15 H15 119.0(12) . . ? 
C15 C16 C17 121.5(2) . . ? 
C15 C16 H16 120.2(11) . . ? 
C17 C16 H16 118.2(11) . . ? 
C16 C17 C18 117.25(19) . . ? 
C16 C17 N2 119.71(17) . . ? 
C18 C17 N2 123.04(18) . . ? 
C19 C18 C17 120.8(2) . . ? 
C19 C18 H18 118.1(12) . . ? 
C17 C18 H18 121.2(12) . . ? 
C14 C19 C18 121.78(19) . . ? 
C14 C19 H19 119.2(12) . . ? 
C18 C19 H19 118.9(12) . . ? 
N2 C20 C21 110.4(2) . . ? 
N2 C20 H20A 109.2(13) . . ? 
C21 C20 H20A 108.0(13) . . ? 
N2 C20 H20B 111.2(11) . . ? 
C21 C20 H20B 107.1(12) . . ? 
H20A C20 H20B 111.0(19) . . ? 
O3 C21 C20 111.9(2) . . ? 
O3 C21 H21A 106.2(14) . . ? 
C20 C21 H21A 108.5(14) . . ? 
O3 C21 H21B 109.0(14) . . ? 
C20 C21 H21B 108.9(14) . . ? 
H21A C21 H21B 112.3(19) . . ? 
O3 C22 C23 111.2(2) . . ? 
O3 C22 H22A 108.2(12) . . ? 
C23 C22 H22A 110.7(13) . . ? 
O3 C22 H22B 108.7(14) . . ? 
C23 C22 H22B 107.4(14) . . ? 
H22A C22 H22B 110.7(19) . . ? 
N2 C23 C22 111.37(18) . . ? 
N2 C23 H23A 109.7(13) . . ? 
C22 C23 H23A 109.1(12) . . ? 
N2 C23 H23B 110.7(11) . . ? 
C22 C23 H23B 107.3(11) . . ? 
H23A C23 H23B 108.6(17) . . ? 
 
_diffrn_measured_fraction_theta_max    0.879 
_diffrn_reflns_theta_full              25.25 
_diffrn_measured_fraction_theta_full   0.879 
_refine_diff_density_max    0.260 
_refine_diff_density_min   -0.294 
_refine_diff_density_rms    0.069 
