
# ol990628i.cif
  
data_k98148 
  
_audit_creation_method            SHELXL-97 
_chemical_name_systematic 
; 
 ? 
; 
_chemical_name_common             ? 
_chemical_melting_point           ? 
_chemical_formula_moiety          ? 
_chemical_formula_sum 
 'C26 H42 N2 O3' 
_chemical_formula_weight          430.62 
  
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 
  
loop_ 
 _symmetry_equiv_pos_as_xyz 
 'x, y, z' 
 '-x, -y, -z' 
  
_cell_length_a                    7.4729(4) 
_cell_length_b                    12.4337(7) 
_cell_length_c                    14.4929(9) 
_cell_angle_alpha                 79.296(3) 
_cell_angle_beta                  80.363(3) 
_cell_angle_gamma                 75.546(3) 
_cell_volume                      1270.90(13) 
_cell_formula_units_Z             2 
_cell_measurement_temperature     125.0(1) 
_cell_measurement_reflns_used     ? 
_cell_measurement_theta_min       ? 
_cell_measurement_theta_max       ? 
  
_exptl_crystal_description        'block cut from needle' 
_exptl_crystal_colour             'colourless' 
_exptl_crystal_size_max           0.37 
_exptl_crystal_size_mid           0.35 
_exptl_crystal_size_min           0.29 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_diffrn     1.125 
_exptl_crystal_density_method     'not measured' 
_exptl_crystal_F_000              472 
_exptl_absorpt_coefficient_mu     0.073 
_exptl_absorpt_correction_type    none 
_exptl_absorpt_correction_T_min   ? 
_exptl_absorpt_correction_T_max   ? 
_exptl_absorpt_process_details    ? 
  
_exptl_special_details 
; 
 ? 
; 
  
_diffrn_ambient_temperature       125.0(1)
_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   'Nonius Kappa-CCD' 
_diffrn_measurement_method        'φ scans and ω scans with κ offsets' 
_diffrn_detector_area_resol_mean  ? 
_diffrn_standards_number          ? 
_diffrn_standards_interval_count  ? 
_diffrn_standards_interval_time   ? 
_diffrn_standards_decay_%         ? 
_diffrn_reflns_number             11420 
_diffrn_reflns_av_R_equivalents   0.050  
_diffrn_reflns_av_sigmaI/netI     0.0654 
_diffrn_reflns_limit_h_min        0 
_diffrn_reflns_limit_h_max        8 
_diffrn_reflns_limit_k_min        -13 
_diffrn_reflns_limit_k_max        14 
_diffrn_reflns_limit_l_min        -16 
_diffrn_reflns_limit_l_max        17 
_diffrn_reflns_theta_min          4.13 
_diffrn_reflns_theta_max          25.07 
_reflns_number_total              4460 
_reflns_number_gt                 3154 
_reflns_threshold_expression      >2sigma(I) 
  
_computing_data_collection        'KappaCCD server software (Nonius, 1997)' 
_computing_cell_refinement        'Denzo-SMN (Otwinowski & Minor, 1997)' 
_computing_data_reduction         'Denzo-SMN (Otwinowski & Minor, 1997)' 
_computing_structure_solution     'SHELXS-97 (Sheldrick, 1990)' 
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 1997)' 
_computing_molecular_graphics     'Bruker SHELXTL V5.1' 
_computing_publication_material   'Bruker SHELXTL V5.1' 

_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)+(0.0815P)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      SHELXL 
_refine_ls_extinction_coef        0.010(5) 
_refine_ls_extinction_expression 
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^' 
_refine_ls_number_reflns          4460 
_refine_ls_number_parameters      289 
_refine_ls_number_restraints      0 
_refine_ls_R_factor_all           0.0734 
_refine_ls_R_factor_gt            0.0463 
_refine_ls_wR_factor_ref          0.1359 
_refine_ls_wR_factor_gt           0.1231 
_refine_ls_goodness_of_fit_ref    1.010 
_refine_ls_restrained_S_all       1.010 
_refine_ls_shift/su_max           0.001 
_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 
O1 O 0.47458(17) 0.29311(10) 0.18446(9) 0.0362(3) Uani 1 1 d . . . 
O2 O 0.28591(15) 0.43937(9) 0.25482(9) 0.0290(3) Uani 1 1 d . . . 
O3 O 0.22387(15) 0.16234(9) 0.26188(8) 0.0280(3) Uani 1 1 d . . . 
N1 N 0.41583(19) 0.50993(11) 0.20776(11) 0.0309(4) Uani 1 1 d . . . 
N2 N 0.05523(18) 0.15226(11) 0.22826(10) 0.0257(3) Uani 1 1 d . . . 
C1 C 0.3387(2) 0.33170(14) 0.23536(12) 0.0289(4) Uani 1 1 d . . . 
C2 C 0.1969(2) 0.26741(13) 0.29404(12) 0.0275(4) Uani 1 1 d . . . 
H2A H 0.0675 0.3123 0.2869 0.033 Uiso 1 1 calc R . . 
C3 C 0.2308(2) 0.25110(14) 0.39701(13) 0.0292(4) Uani 1 1 d . . . 
C4 C 0.1224(3) 0.32140(15) 0.45898(14) 0.0370(5) Uani 1 1 d . . . 
H4A H 0.0220 0.3794 0.4377 0.044 Uiso 1 1 calc R . . 
C5 C 0.1588(3) 0.30788(17) 0.55173(14) 0.0428(5) Uani 1 1 d . . . 
H5A H 0.0832 0.3563 0.5937 0.051 Uiso 1 1 calc R . . 
C6 C 0.3057(3) 0.22360(16) 0.58311(14) 0.0419(5) Uani 1 1 d . . . 
H6A H 0.3312 0.2142 0.6465 0.050 Uiso 1 1 calc R . . 
C7 C 0.4144(3) 0.15363(15) 0.52193(14) 0.0385(5) Uani 1 1 d . . . 
H7A H 0.5150 0.0959 0.5434 0.046 Uiso 1 1 calc R . . 
C8 C 0.3781(3) 0.16679(14) 0.42894(13) 0.0335(4) Uani 1 1 d . . . 
H8A H 0.4539 0.1182 0.3872 0.040 Uiso 1 1 calc R . . 
C9 C 0.5110(2) 0.53158(15) 0.28283(14) 0.0363(5) Uani 1 1 d . . . 
C10 C 0.6390(3) 0.60846(16) 0.23051(16) 0.0442(5) Uani 1 1 d . . . 
H10A H 0.7011 0.6300 0.2772 0.053 Uiso 1 1 calc R . . 
H10B H 0.7370 0.5663 0.1873 0.053 Uiso 1 1 calc R . . 
C11 C 0.5359(3) 0.71465(16) 0.17335(15) 0.0423(5) Uani 1 1 d . . . 
H11A H 0.4432 0.7603 0.2163 0.051 Uiso 1 1 calc R . . 
H11B H 0.6252 0.7602 0.1398 0.051 Uiso 1 1 calc R . . 
C12 C 0.4381(3) 0.68260(16) 0.10210(15) 0.0424(5) Uani 1 1 d . . . 
H12A H 0.5332 0.6438 0.0556 0.051 Uiso 1 1 calc R . . 
H12B H 0.3671 0.7519 0.0672 0.051 Uiso 1 1 calc R . . 
C13 C 0.3042(2) 0.60573(14) 0.14786(13) 0.0312(4) Uani 1 1 d . . . 
C14 C 0.6324(3) 0.41741(17) 0.32192(18) 0.0552(6) Uani 1 1 d . . . 
H14A H 0.7058 0.3806 0.2691 0.083 Uiso 1 1 calc R . . 
H14B H 0.5519 0.3695 0.3594 0.083 Uiso 1 1 calc R . . 
H14C H 0.7165 0.4297 0.3621 0.083 Uiso 1 1 calc R . . 
C15 C 0.3846(3) 0.58159(16) 0.36638(14) 0.0428(5) Uani 1 1 d . . . 
H15A H 0.3256 0.6601 0.3454 0.064 Uiso 1 1 calc R . . 
H15B H 0.4592 0.5778 0.4169 0.064 Uiso 1 1 calc R . . 
H15C H 0.2883 0.5388 0.3902 0.064 Uiso 1 1 calc R . . 
C16 C 0.2502(3) 0.55526(16) 0.07061(14) 0.0411(5) Uani 1 1 d . . . 
H16A H 0.1489 0.5172 0.0975 0.062 Uiso 1 1 calc R . . 
H16B H 0.3583 0.5010 0.0456 0.062 Uiso 1 1 calc R . . 
H16C H 0.2088 0.6153 0.0194 0.062 Uiso 1 1 calc R . . 
C17 C 0.1250(2) 0.67211(15) 0.19875(14) 0.0351(5) Uani 1 1 d . . . 
H17A H 0.0546 0.6197 0.2381 0.053 Uiso 1 1 calc R . . 
H17B H 0.0488 0.7210 0.1517 0.053 Uiso 1 1 calc R . . 
H17C H 0.1572 0.7181 0.2388 0.053 Uiso 1 1 calc R . . 
C18 C 0.1041(2) 0.14329(15) 0.12507(12) 0.0328(4) Uani 1 1 d . . . 
C19 C -0.0678(3) 0.12244(16) 0.09179(13) 0.0363(5) Uani 1 1 d . . . 
H19A H -0.1696 0.1907 0.0944 0.044 Uiso 1 1 calc R . . 
H19B H -0.0364 0.1098 0.0250 0.044 Uiso 1 1 calc R . . 
C20 C -0.1371(3) 0.02248(15) 0.15055(14) 0.0392(5) Uani 1 1 d . . . 
H20A H -0.2504 0.0150 0.1277 0.047 Uiso 1 1 calc R . . 
H20B H -0.0404 -0.0476 0.1449 0.047 Uiso 1 1 calc R . . 
C21 C -0.1809(3) 0.04219(15) 0.25325(13) 0.0344(4) Uani 1 1 d . . . 
H21A H -0.2242 -0.0230 0.2922 0.041 Uiso 1 1 calc R . . 
H21B H -0.2842 0.1093 0.2581 0.041 Uiso 1 1 calc R . . 
C22 C -0.0145(2) 0.05923(13) 0.29406(12) 0.0285(4) Uani 1 1 d . . . 
C23 C 0.2801(3) 0.05424(18) 0.09865(15) 0.0485(6) Uani 1 1 d . . . 
H23A H 0.2529 -0.0206 0.1156 0.073 Uiso 1 1 calc R . . 
H23B H 0.3799 0.0581 0.1331 0.073 Uiso 1 1 calc R . . 
H23C H 0.3197 0.0685 0.0304 0.073 Uiso 1 1 calc R . . 
C24 C 0.1337(3) 0.25863(17) 0.07492(14) 0.0452(5) Uani 1 1 d . . . 
H24A H 0.0329 0.3177 0.0991 0.068 Uiso 1 1 calc R . . 
H24B H 0.1337 0.2635 0.0066 0.068 Uiso 1 1 calc R . . 
H24C H 0.2534 0.2685 0.0870 0.068 Uiso 1 1 calc R . . 
C25 C 0.1318(3) -0.05197(14) 0.31090(15) 0.0415(5) Uani 1 1 d . . . 
H25A H 0.2458 -0.0366 0.3251 0.062 Uiso 1 1 calc R . . 
H25B H 0.1598 -0.0881 0.2539 0.062 Uiso 1 1 calc R . . 
H25C H 0.0827 -0.1019 0.3644 0.062 Uiso 1 1 calc R . . 
C26 C -0.0862(3) 0.10007(15) 0.38937(13) 0.0344(4) Uani 1 1 d . . . 
H26A H 0.0190 0.1067 0.4185 0.052 Uiso 1 1 calc R . . 
H26B H -0.1508 0.0461 0.4310 0.052 Uiso 1 1 calc R . . 
H26C H -0.1727 0.1735 0.3798 0.052 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 
O1 C1 1.201(2) . ? 
O2 C1 1.3664(19) . ? 
O2 N1 1.4692(18) . ? 
O3 C2 1.4241(19) . ? 
O3 N2 1.4658(16) . ? 
N1 C9 1.492(2) . ? 
N1 C13 1.494(2) . ? 
N2 C18 1.497(2) . ? 
N2 C22 1.498(2) . ? 
C1 C2 1.534(2) . ? 
C2 C3 1.523(2) . ? 
C3 C4 1.386(2) . ? 
C3 C8 1.393(2) . ? 
C4 C5 1.387(3) . ? 
C5 C6 1.388(3) . ? 
C6 C7 1.377(3) . ? 
C7 C8 1.391(3) . ? 
C9 C10 1.532(3) . ? 
C9 C15 1.533(3) . ? 
C9 C14 1.546(2) . ? 
C10 C11 1.524(3) . ? 
C11 C12 1.520(3) . ? 
C12 C13 1.541(3) . ? 
C13 C16 1.533(2) . ? 
C13 C17 1.537(2) . ? 
C18 C24 1.533(3) . ? 
C18 C23 1.538(3) . ? 
C18 C19 1.539(2) . ? 
C19 C20 1.523(3) . ? 
C20 C21 1.521(3) . ? 
C21 C22 1.538(2) . ? 
C22 C26 1.526(2) . ? 
C22 C25 1.541(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 O2 N1 113.61(13) . . ? 
C2 O3 N2 111.15(11) . . ? 
O2 N1 C9 107.10(13) . . ? 
O2 N1 C13 105.73(12) . . ? 
C9 N1 C13 120.17(13) . . ? 
O3 N2 C18 106.88(12) . . ? 
O3 N2 C22 106.96(11) . . ? 
C18 N2 C22 119.03(13) . . ? 
O1 C1 O2 126.52(16) . . ? 
O1 C1 C2 126.12(15) . . ? 
O2 C1 C2 107.31(14) . . ? 
O3 C2 C3 111.26(13) . . ? 
O3 C2 C1 109.08(14) . . ? 
C3 C2 C1 107.03(13) . . ? 
C4 C3 C8 119.05(16) . . ? 
C4 C3 C2 121.35(15) . . ? 
C8 C3 C2 119.55(15) . . ? 
C3 C4 C5 120.71(17) . . ? 
C4 C5 C6 119.94(18) . . ? 
C7 C6 C5 119.72(17) . . ? 
C6 C7 C8 120.51(17) . . ? 
C7 C8 C3 120.08(17) . . ? 
N1 C9 C10 104.85(16) . . ? 
N1 C9 C15 116.45(14) . . ? 
C10 C9 C15 111.56(15) . . ? 
N1 C9 C14 106.69(14) . . ? 
C10 C9 C14 108.85(16) . . ? 
C15 C9 C14 108.14(17) . . ? 
C11 C10 C9 113.12(15) . . ? 
C12 C11 C10 109.43(15) . . ? 
C11 C12 C13 113.32(16) . . ? 
N1 C13 C16 106.24(13) . . ? 
N1 C13 C17 116.15(15) . . ? 
C16 C13 C17 108.12(15) . . ? 
N1 C13 C12 105.73(14) . . ? 
C16 C13 C12 109.25(16) . . ? 
C17 C13 C12 111.10(14) . . ? 
N2 C18 C24 106.43(14) . . ? 
N2 C18 C23 115.79(15) . . ? 
C24 C18 C23 108.17(16) . . ? 
N2 C18 C19 106.85(14) . . ? 
C24 C18 C19 108.14(15) . . ? 
C23 C18 C19 111.15(15) . . ? 
C20 C19 C18 113.59(15) . . ? 
C21 C20 C19 108.14(14) . . ? 
C20 C21 C22 113.89(16) . . ? 
N2 C22 C26 107.43(13) . . ? 
N2 C22 C21 106.59(13) . . ? 
C26 C22 C21 108.17(14) . . ? 
N2 C22 C25 115.20(15) . . ? 
C26 C22 C25 108.03(14) . . ? 
C21 C22 C25 111.17(14) . . ? 
  
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 
C1 O2 N1 C9 -109.77(14) . . . . ? 
C1 O2 N1 C13 120.96(14) . . . . ? 
C2 O3 N2 C18 116.94(14) . . . . ? 
C2 O3 N2 C22 -114.55(14) . . . . ? 
N1 O2 C1 O1 -1.0(2) . . . . ? 
N1 O2 C1 C2 176.51(11) . . . . ? 
N2 O3 C2 C3 121.85(14) . . . . ? 
N2 O3 C2 C1 -120.30(13) . . . . ? 
O1 C1 C2 O3 -14.2(2) . . . . ? 
O2 C1 C2 O3 168.23(12) . . . . ? 
O1 C1 C2 C3 106.26(19) . . . . ? 
O2 C1 C2 C3 -71.30(15) . . . . ? 
O3 C2 C3 C4 -142.31(16) . . . . ? 
C1 C2 C3 C4 98.62(19) . . . . ? 
O3 C2 C3 C8 40.3(2) . . . . ? 
C1 C2 C3 C8 -78.78(19) . . . . ? 
C8 C3 C4 C5 -0.4(3) . . . . ? 
C2 C3 C4 C5 -177.81(17) . . . . ? 
C3 C4 C5 C6 0.3(3) . . . . ? 
C4 C5 C6 C7 -0.1(3) . . . . ? 
C5 C6 C7 C8 0.0(3) . . . . ? 
C6 C7 C8 C3 -0.1(3) . . . . ? 
C4 C3 C8 C7 0.3(3) . . . . ? 
C2 C3 C8 C7 177.73(17) . . . . ? 
O2 N1 C9 C10 -178.08(12) . . . . ? 
C13 N1 C9 C10 -57.62(19) . . . . ? 
O2 N1 C9 C15 -54.27(18) . . . . ? 
C13 N1 C9 C15 66.2(2) . . . . ? 
O2 N1 C9 C14 66.55(18) . . . . ? 
C13 N1 C9 C14 -172.99(16) . . . . ? 
N1 C9 C10 C11 55.2(2) . . . . ? 
C15 C9 C10 C11 -71.7(2) . . . . ? 
C14 C9 C10 C11 169.07(17) . . . . ? 
C9 C10 C11 C12 -58.0(2) . . . . ? 
C10 C11 C12 C13 56.2(2) . . . . ? 
O2 N1 C13 C16 -66.52(16) . . . . ? 
C9 N1 C13 C16 172.34(16) . . . . ? 
O2 N1 C13 C17 53.74(18) . . . . ? 
C9 N1 C13 C17 -67.4(2) . . . . ? 
O2 N1 C13 C12 177.45(13) . . . . ? 
C9 N1 C13 C12 56.3(2) . . . . ? 
C11 C12 C13 N1 -52.30(19) . . . . ? 
C11 C12 C13 C16 -166.27(15) . . . . ? 
C11 C12 C13 C17 74.5(2) . . . . ? 
O3 N2 C18 C24 -69.43(16) . . . . ? 
C22 N2 C18 C24 169.44(14) . . . . ? 
O3 N2 C18 C23 50.81(18) . . . . ? 
C22 N2 C18 C23 -70.3(2) . . . . ? 
O3 N2 C18 C19 175.21(12) . . . . ? 
C22 N2 C18 C19 54.07(18) . . . . ? 
N2 C18 C19 C20 -53.90(19) . . . . ? 
C24 C18 C19 C20 -168.11(15) . . . . ? 
C23 C18 C19 C20 73.3(2) . . . . ? 
C18 C19 C20 C21 57.4(2) . . . . ? 
C19 C20 C21 C22 -57.6(2) . . . . ? 
O3 N2 C22 C26 69.18(15) . . . . ? 
C18 N2 C22 C26 -169.73(13) . . . . ? 
O3 N2 C22 C21 -175.06(12) . . . . ? 
C18 N2 C22 C21 -53.97(18) . . . . ? 
O3 N2 C22 C25 -51.24(17) . . . . ? 
C18 N2 C22 C25 69.85(19) . . . . ? 
C20 C21 C22 N2 53.99(18) . . . . ? 
C20 C21 C22 C26 169.26(14) . . . . ? 
C20 C21 C22 C25 -72.30(19) . . . . ? 
  
_diffrn_measured_fraction_theta_max    0.993 
_diffrn_reflns_theta_full              25.07 
_diffrn_measured_fraction_theta_full   0.993 
_refine_diff_density_max    0.266 
_refine_diff_density_min   -0.240 
_refine_diff_density_rms    0.047 
  

