  
data_230417a 
  
_audit_creation_method            SHELXL-97 
_chemical_name_systematic 
; 
 ? 
; 
_chemical_name_common             ? 
_chemical_melting_point           ? 
_chemical_formula_moiety          ? 
_chemical_formula_sum 
 'C20 H19 N O' 
_chemical_formula_weight          289.36 
  
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                    5.6735(6) 
_cell_length_b                    19.723(2) 
_cell_length_c                    14.1155(17) 
_cell_angle_alpha                 90.00 
_cell_angle_beta                  101.542(4) 
_cell_angle_gamma                 90.00 
_cell_volume                      1547.6(3) 
_cell_formula_units_Z             4 
_cell_measurement_temperature     298(2) 
_cell_measurement_reflns_used     1724 
_cell_measurement_theta_min       2.537 
_cell_measurement_theta_max       28.307 
  
_exptl_crystal_description        ? 
_exptl_crystal_colour             ? 
_exptl_crystal_size_max           0.21 
_exptl_crystal_size_mid           0.17 
_exptl_crystal_size_min           0.05 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_diffrn     1.242 
_exptl_crystal_density_method     'not measured' 
_exptl_crystal_F_000              616 
_exptl_absorpt_coefficient_mu     0.076 
_exptl_absorpt_correction_type    multi-scan 
_exptl_absorpt_correction_T_min   0.9842 
_exptl_absorpt_correction_T_max   0.9962 
_exptl_absorpt_process_details    sadabs 
  
_exptl_special_details 
; 
 ? 
; 
  
_diffrn_ambient_temperature       298(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   '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             2652 
_diffrn_reflns_av_R_equivalents   0.0000 
_diffrn_reflns_av_sigmaI/netI     0.3672 
_diffrn_reflns_limit_h_min        -6 
_diffrn_reflns_limit_h_max        6 
_diffrn_reflns_limit_k_min        0 
_diffrn_reflns_limit_k_max        23 
_diffrn_reflns_limit_l_min        0 
_diffrn_reflns_limit_l_max        16 
_diffrn_reflns_theta_min          2.07 
_diffrn_reflns_theta_max          25.02 
_reflns_number_total              2652 
_reflns_number_gt                 876 
_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)+(0.0430P)²+6.7522P] 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      SHELXL 
_refine_ls_extinction_coef        0.013(7) 
_refine_ls_extinction_expression 
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^' 
_refine_ls_number_reflns          2652 
_refine_ls_number_parameters      201 
_refine_ls_number_restraints      396 
_refine_ls_R_factor_all           0.5194 
_refine_ls_R_factor_gt            0.1981 
_refine_ls_wR_factor_ref          0.4151 
_refine_ls_wR_factor_gt           0.3240 
_refine_ls_goodness_of_fit_ref    1.237 
_refine_ls_restrained_S_all       1.156 
_refine_ls_shift/su_max           0.006 
_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 0.3693(18) 0.6510(5) 0.9182(7) 0.057(2) Uani 1 1 d U . . 
O1 O 0.6201(16) 0.6983(4) 0.8328(7) 0.079(3) Uani 1 1 d . . . 
C1 C 0.528(2) 0.7007(6) 0.9047(10) 0.057(3) Uani 1 1 d U . . 
C2 C 0.582(2) 0.7598(6) 0.9733(9) 0.055(3) Uani 1 1 d U . . 
H2 H 0.7558 0.7618 0.9974 0.066 Uiso 1 1 calc R . . 
C3 C 0.454(2) 0.7625(6) 1.0626(9) 0.051(3) Uani 1 1 d U . . 
H3 H 0.5748 0.7663 1.1225 0.061 Uiso 1 1 calc R . . 
C4 C 0.296(2) 0.7021(6) 1.0682(9) 0.055(3) Uani 1 1 d U . . 
C5 C 0.256(2) 0.6511(6) 1.0034(9) 0.053(3) Uani 1 1 d U . . 
C6 C 0.098(2) 0.5973(6) 1.0113(9) 0.060(3) Uani 1 1 d U . . 
H6 H 0.0729 0.5626 0.9658 0.072 Uiso 1 1 calc R . . 
C7 C -0.019(2) 0.5975(7) 1.0896(10) 0.066(3) Uani 1 1 d U . . 
H7 H -0.1264 0.5628 1.0956 0.079 Uiso 1 1 calc R . . 
C8 C 0.021(2) 0.6469(7) 1.1559(10) 0.069(3) Uani 1 1 d U . . 
H8 H -0.0587 0.6458 1.2073 0.082 Uiso 1 1 calc R . . 
C9 C 0.178(2) 0.6991(6) 1.1497(9) 0.065(3) Uani 1 1 d U . . 
H9 H 0.2077 0.7322 1.1976 0.078 Uiso 1 1 calc R . . 
C10 C 0.501(3) 0.8264(6) 0.9198(12) 0.076(4) Uani 1 1 d . . . 
H10 H 0.5206 0.8277 0.8524 0.091 Uiso 1 1 calc R . . 
C11 C 0.614(3) 0.8868(6) 0.9817(11) 0.082(5) Uani 1 1 d . . . 
H11A H 0.5887 0.9287 0.9449 0.099 Uiso 1 1 calc R . . 
H11B H 0.7850 0.8801 1.0044 0.099 Uiso 1 1 calc R . . 
C12 C 0.481(3) 0.8887(6) 1.0675(10) 0.076(4) Uani 1 1 d . . . 
H12A H 0.5914 0.8827 1.1289 0.091 Uiso 1 1 calc R . . 
H12B H 0.3928 0.9308 1.0688 0.091 Uiso 1 1 calc R . . 
C13 C 0.311(2) 0.8283(6) 1.0442(10) 0.065(4) Uani 1 1 d . . . 
H13 H 0.1720 0.8301 1.0758 0.078 Uiso 1 1 calc R . . 
C14 C 0.242(3) 0.8304(6) 0.9331(12) 0.077(4) Uani 1 1 d . . . 
H14A H 0.1466 0.7918 0.9059 0.093 Uiso 1 1 calc R . . 
H14B H 0.1636 0.8724 0.9088 0.093 Uiso 1 1 calc R . . 
C15 C 0.319(2) 0.5967(6) 0.8497(9) 0.061(3) Uani 1 1 d DU . . 
C16 C 0.484(2) 0.5449(5) 0.8512(9) 0.067(3) Uani 1 1 d DU . . 
H16 H 0.6292 0.5461 0.8957 0.081 Uiso 1 1 calc R . . 
C17 C 0.435(2) 0.4912(6) 0.7868(9) 0.070(4) Uani 1 1 d DU . . 
H17 H 0.5463 0.4563 0.7888 0.084 Uiso 1 1 calc R . . 
C18 C 0.221(2) 0.4891(6) 0.7197(9) 0.069(4) Uani 1 1 d DU . . 
H18 H 0.1888 0.4533 0.6761 0.082 Uiso 1 1 calc R . . 
C19 C 0.056(2) 0.5407(6) 0.7179(9) 0.072(4) Uani 1 1 d DU . . 
H19 H -0.0914 0.5389 0.6748 0.086 Uiso 1 1 calc R . . 
C20 C 0.109(2) 0.5954(6) 0.7806(9) 0.065(3) Uani 1 1 d DU . . 
H20 H 0.0015 0.6315 0.7761 0.077 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 C1 1.370(14) . ? 
N1 C15 1.433(14) . ? 
N1 C5 1.474(15) . ? 
O1 C1 1.232(13) . ? 
C1 C2 1.507(16) . ? 
C2 C10 1.539(17) . ? 
C2 C3 1.576(16) . ? 
C2 H2 0.9800 . ? 
C3 C4 1.502(15) . ? 
C3 C13 1.525(16) . ? 
C3 H3 0.9800 . ? 
C4 C5 1.349(16) . ? 
C4 C9 1.443(17) . ? 
C5 C6 1.405(15) . ? 
C6 C7 1.400(17) . ? 
C6 H6 0.9300 . ? 
C7 C8 1.339(16) . ? 
C7 H7 0.9300 . ? 
C8 C9 1.375(16) . ? 
C8 H8 0.9300 . ? 
C9 H9 0.9300 . ? 
C10 C14 1.519(17) . ? 
C10 C11 1.538(18) . ? 
C10 H10 0.9800 . ? 
C11 C12 1.551(17) . ? 
C11 H11A 0.9700 . ? 
C11 H11B 0.9700 . ? 
C12 C13 1.527(16) . ? 
C12 H12A 0.9700 . ? 
C12 H12B 0.9700 . ? 
C13 C14 1.538(18) . ? 
C13 H13 0.9800 . ? 
C14 H14A 0.9700 . ? 
C14 H14B 0.9700 . ? 
C15 C20 1.381(8) . ? 
C15 C16 1.385(8) . ? 
C16 C17 1.388(8) . ? 
C16 H16 0.9300 . ? 
C17 C18 1.382(8) . ? 
C17 H17 0.9300 . ? 
C18 C19 1.382(8) . ? 
C18 H18 0.9300 . ? 
C19 C20 1.389(8) . ? 
C19 H19 0.9300 . ? 
C20 H20 0.9300 . ? 
  
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 N1 C15 119.2(11) . . ? 
C1 N1 C5 121.3(10) . . ? 
C15 N1 C5 119.4(10) . . ? 
O1 C1 N1 119.1(12) . . ? 
O1 C1 C2 119.6(12) . . ? 
N1 C1 C2 121.2(11) . . ? 
C1 C2 C10 110.1(11) . . ? 
C1 C2 C3 118.3(10) . . ? 
C10 C2 C3 103.0(10) . . ? 
C1 C2 H2 108.3 . . ? 
C10 C2 H2 108.3 . . ? 
C3 C2 H2 108.3 . . ? 
C4 C3 C13 112.3(10) . . ? 
C4 C3 C2 113.0(10) . . ? 
C13 C3 C2 101.9(9) . . ? 
C4 C3 H3 109.8 . . ? 
C13 C3 H3 109.8 . . ? 
C2 C3 H3 109.8 . . ? 
C5 C4 C9 117.9(12) . . ? 
C5 C4 C3 125.2(12) . . ? 
C9 C4 C3 116.9(11) . . ? 
C4 C5 C6 122.2(12) . . ? 
C4 C5 N1 120.8(11) . . ? 
C6 C5 N1 116.9(11) . . ? 
C7 C6 C5 118.1(12) . . ? 
C7 C6 H6 120.9 . . ? 
C5 C6 H6 120.9 . . ? 
C8 C7 C6 120.8(13) . . ? 
C8 C7 H7 119.6 . . ? 
C6 C7 H7 119.6 . . ? 
C7 C8 C9 121.6(13) . . ? 
C7 C8 H8 119.2 . . ? 
C9 C8 H8 119.2 . . ? 
C8 C9 C4 119.3(12) . . ? 
C8 C9 H9 120.3 . . ? 
C4 C9 H9 120.3 . . ? 
C14 C10 C11 101.0(11) . . ? 
C14 C10 C2 100.5(10) . . ? 
C11 C10 C2 109.6(12) . . ? 
C14 C10 H10 114.7 . . ? 
C11 C10 H10 114.7 . . ? 
C2 C10 H10 114.7 . . ? 
C10 C11 C12 104.5(11) . . ? 
C10 C11 H11A 110.8 . . ? 
C12 C11 H11A 110.8 . . ? 
C10 C11 H11B 110.8 . . ? 
C12 C11 H11B 110.8 . . ? 
H11A C11 H11B 108.9 . . ? 
C13 C12 C11 101.4(10) . . ? 
C13 C12 H12A 111.5 . . ? 
C11 C12 H12A 111.5 . . ? 
C13 C12 H12B 111.5 . . ? 
C11 C12 H12B 111.5 . . ? 
H12A C12 H12B 109.3 . . ? 
C3 C13 C12 109.6(11) . . ? 
C3 C13 C14 102.4(10) . . ? 
C12 C13 C14 102.6(11) . . ? 
C3 C13 H13 113.7 . . ? 
C12 C13 H13 113.7 . . ? 
C14 C13 H13 113.7 . . ? 
C10 C14 C13 94.2(11) . . ? 
C10 C14 H14A 112.9 . . ? 
C13 C14 H14A 112.9 . . ? 
C10 C14 H14B 112.9 . . ? 
C13 C14 H14B 112.9 . . ? 
H14A C14 H14B 110.3 . . ? 
C20 C15 C16 118.9(12) . . ? 
C20 C15 N1 121.2(10) . . ? 
C16 C15 N1 119.9(10) . . ? 
C15 C16 C17 120.4(12) . . ? 
C15 C16 H16 119.8 . . ? 
C17 C16 H16 119.8 . . ? 
C18 C17 C16 120.4(13) . . ? 
C18 C17 H17 119.8 . . ? 
C16 C17 H17 119.8 . . ? 
C19 C18 C17 119.4(12) . . ? 
C19 C18 H18 120.3 . . ? 
C17 C18 H18 120.3 . . ? 
C18 C19 C20 120.0(13) . . ? 
C18 C19 H19 120.0 . . ? 
C20 C19 H19 120.0 . . ? 
C15 C20 C19 120.7(12) . . ? 
C15 C20 H20 119.6 . . ? 
C19 C20 H20 119.6 . . ? 
  
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 
C15 N1 C1 O1 1.4(18) . . . . ? 
C5 N1 C1 O1 179.4(12) . . . . ? 
C15 N1 C1 C2 178.3(11) . . . . ? 
C5 N1 C1 C2 -3.7(17) . . . . ? 
O1 C1 C2 C10 60.0(16) . . . . ? 
N1 C1 C2 C10 -116.9(13) . . . . ? 
O1 C1 C2 C3 178.0(11) . . . . ? 
N1 C1 C2 C3 1.1(18) . . . . ? 
C1 C2 C3 C4 1.7(16) . . . . ? 
C10 C2 C3 C4 123.4(11) . . . . ? 
C1 C2 C3 C13 -119.1(12) . . . . ? 
C10 C2 C3 C13 2.6(12) . . . . ? 
C13 C3 C4 C5 112.5(14) . . . . ? 
C2 C3 C4 C5 -2.1(18) . . . . ? 
C13 C3 C4 C9 -67.5(14) . . . . ? 
C2 C3 C4 C9 177.9(11) . . . . ? 
C9 C4 C5 C6 2(2) . . . . ? 
C3 C4 C5 C6 -177.6(11) . . . . ? 
C9 C4 C5 N1 179.8(11) . . . . ? 
C3 C4 C5 N1 0(2) . . . . ? 
C1 N1 C5 C4 3.4(18) . . . . ? 
C15 N1 C5 C4 -178.6(11) . . . . ? 
C1 N1 C5 C6 -179.1(11) . . . . ? 
C15 N1 C5 C6 -1.1(16) . . . . ? 
C4 C5 C6 C7 -0.2(19) . . . . ? 
N1 C5 C6 C7 -177.6(12) . . . . ? 
C5 C6 C7 C8 -1(2) . . . . ? 
C6 C7 C8 C9 0(2) . . . . ? 
C7 C8 C9 C4 2(2) . . . . ? 
C5 C4 C9 C8 -3.4(19) . . . . ? 
C3 C4 C9 C8 176.6(11) . . . . ? 
C1 C2 C10 C14 88.9(13) . . . . ? 
C3 C2 C10 C14 -38.2(13) . . . . ? 
C1 C2 C10 C11 -165.4(11) . . . . ? 
C3 C2 C10 C11 67.5(12) . . . . ? 
C14 C10 C11 C12 34.9(15) . . . . ? 
C2 C10 C11 C12 -70.5(14) . . . . ? 
C10 C11 C12 C13 0.6(15) . . . . ? 
C4 C3 C13 C12 164.0(11) . . . . ? 
C2 C3 C13 C12 -74.8(12) . . . . ? 
C4 C3 C13 C14 -87.7(12) . . . . ? 
C2 C3 C13 C14 33.5(12) . . . . ? 
C11 C12 C13 C3 72.4(14) . . . . ? 
C11 C12 C13 C14 -35.8(13) . . . . ? 
C11 C10 C14 C13 -55.0(12) . . . . ? 
C2 C10 C14 C13 57.5(11) . . . . ? 
C3 C13 C14 C10 -56.8(11) . . . . ? 
C12 C13 C14 C10 56.8(11) . . . . ? 
C1 N1 C15 C20 -102.4(14) . . . . ? 
C5 N1 C15 C20 79.5(16) . . . . ? 
C1 N1 C15 C16 76.7(15) . . . . ? 
C5 N1 C15 C16 -101.4(14) . . . . ? 
C20 C15 C16 C17 -3(2) . . . . ? 
N1 C15 C16 C17 178.4(12) . . . . ? 
C15 C16 C17 C18 1(2) . . . . ? 
C16 C17 C18 C19 -1(2) . . . . ? 
C17 C18 C19 C20 3(2) . . . . ? 
C16 C15 C20 C19 4(2) . . . . ? 
N1 C15 C20 C19 -176.5(12) . . . . ? 
C18 C19 C20 C15 -4(2) . . . . ? 
  
_diffrn_measured_fraction_theta_max    0.968 
_diffrn_reflns_theta_full              25.02 
_diffrn_measured_fraction_theta_full   0.968 
_refine_diff_density_max    0.315 
_refine_diff_density_min   -0.322 
_refine_diff_density_rms    0.076 
