 
data_s001
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 ?
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C27 H29 N O4'
_chemical_formula_weight          431.51
 
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    C12/c1
 
loop_
 _symmetry_equiv_pos_as_xyz
 'x, y, z'
 '-x, y, -z+1/2'
 'x+1/2, y+1/2, z'
 '-x+1/2, y+1/2, -z+1/2'
 '-x, -y, -z'
 'x, -y, z-1/2'
 '-x+1/2, -y+1/2, -z'
 'x+1/2, -y+1/2, z-1/2'
 
_cell_length_a                    21.5033(15)
_cell_length_b                    6.2034(4)
_cell_length_c                    19.1972(13)
_cell_angle_alpha                 90.00
_cell_angle_beta                  114.465(7)
_cell_angle_gamma                 90.00
_cell_volume                      2330.9(3)
_cell_formula_units_Z             4
_cell_measurement_temperature     120(2)
_cell_measurement_reflns_used     ?
_cell_measurement_theta_min       ?
_cell_measurement_theta_max       ?
 
_exptl_crystal_description        needle
_exptl_crystal_colour             colourless
_exptl_crystal_size_max           0.70
_exptl_crystal_size_mid           0.16
_exptl_crystal_size_min           0.16
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.230
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              920
_exptl_absorpt_coefficient_mu     0.082
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.9448
_exptl_absorpt_correction_T_max   0.9870
_exptl_absorpt_process_details    'SORTAV Blessing (1997)'
_exptl_special_details
;
 PLEASE NOTE cell_measurement_ fields are not relevant to area detector data,
 the entire data set is used to refine the cell, which is indexed from all
 observed reflections in a 10 degree phi range.
;
_diffrn_ambient_temperature       120(2)
_diffrn_radiation_wavelength      0.71073
_diffrn_radiation_type            MoK\a 
_diffrn_radiation_source          'Nonius FR591 rotating anode'
_diffrn_radiation_monochromator   graphite 
_diffrn_measurement_device_type   'Nonius KappaCCD Area Detector'
_diffrn_measurement_method        'φ and ω scans to fill Ewald Sphere'
_diffrn_detector_area_resol_mean  9.091
_diffrn_standards_number          ?
_diffrn_standards_interval_count  ?
_diffrn_standards_interval_time   ?
_diffrn_standards_decay_%         ?
_diffrn_reflns_number             18501
_diffrn_reflns_av_R_equivalents   0.1403
_diffrn_reflns_av_sigmaI/netI     0.1053
_diffrn_reflns_limit_h_min        -27
_diffrn_reflns_limit_h_max        27
_diffrn_reflns_limit_k_min        -8
_diffrn_reflns_limit_k_max        8
_diffrn_reflns_limit_l_min        -24
_diffrn_reflns_limit_l_max        24
_diffrn_reflns_theta_min          2.33
_diffrn_reflns_theta_max          27.49
_reflns_number_total              2501
_reflns_number_gt                 1582
_reflns_threshold_expression      >2sigma(I)
 
_computing_data_collection
' DENZO (Otwinowski and Minor, 1997)'
_computing_cell_refinement        
' DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998)'
_computing_data_reduction         
' DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998)'
_computing_structure_solution     'SHELXS-97 (Sheldrick, 1997a)' 
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 1997b)' 
_computing_molecular_graphics     'PLATON (Spek, 1990)'
_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)+(0.1603P)²+11.0979P] 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          2501
_refine_ls_number_parameters      149
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.1550
_refine_ls_R_factor_gt            0.1161
_refine_ls_wR_factor_ref          0.3358
_refine_ls_wR_factor_gt           0.3106
_refine_ls_goodness_of_fit_ref    1.044
_refine_ls_restrained_S_all       1.044
_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
C1 C 0.0221(2) 0.2580(6) 0.3148(2) 0.0290(9) Uani 1 1 d . . .
C2 C 0.0243(2) 0.4817(7) 0.3180(2) 0.0311(9) Uani 1 1 d . . .
H2 H 0.0420 0.5546 0.3658 0.037 Uiso 1 1 calc R . .
C3 C 0.0000 0.5962(9) 0.2500 0.0318(13) Uani 1 2 d S . .
H3 H 0.0000 0.7493 0.2500 0.038 Uiso 1 2 calc SR . .
C4 C 0.0443(2) 0.1238(6) 0.3870(2) 0.0301(9) Uani 1 1 d . . .
C5 C 0.1123(3) 0.1240(8) 0.5208(3) 0.0407(11) Uani 1 1 d . . .
H5A H 0.1259 -0.0254 0.5154 0.049 Uiso 1 1 calc R . .
H5B H 0.0756 0.1180 0.5392 0.049 Uiso 1 1 calc R . .
C6 C 0.1723(2) 0.2466(7) 0.5763(2) 0.0344(10) Uani 1 1 d . . .
C7 C 0.1613(2) 0.4366(7) 0.6097(3) 0.0343(10) Uani 1 1 d . . .
C8 C 0.2174(2) 0.5460(7) 0.6631(3) 0.0359(10) Uani 1 1 d . . .
H8 H 0.2100 0.6733 0.6860 0.043 Uiso 1 1 calc R . .
C9 C 0.2833(2) 0.4753(7) 0.6835(3) 0.0357(10) Uani 1 1 d . . .
C10 C 0.2934(2) 0.2897(7) 0.6492(3) 0.0360(10) Uani 1 1 d . . .
H10 H 0.3387 0.2395 0.6629 0.043 Uiso 1 1 calc R . .
C11 C 0.2390(2) 0.1744(7) 0.5950(2) 0.0338(10) Uani 1 1 d . . .
C12 C 0.2548(3) -0.0190(8) 0.5570(3) 0.0469(13) Uani 1 1 d . . .
H12A H 0.2365 0.0051 0.5017 0.070 Uiso 1 1 calc R . .
H12B H 0.2337 -0.1479 0.5674 0.070 Uiso 1 1 calc R . .
H12C H 0.3044 -0.0392 0.5774 0.070 Uiso 1 1 calc R . .
C13 C 0.0903(3) 0.5216(9) 0.5898(4) 0.0514(13) Uani 1 1 d . . .
H13A H 0.0925 0.6437 0.6231 0.077 Uiso 1 1 calc R . .
H13B H 0.0620 0.4073 0.5970 0.077 Uiso 1 1 calc R . .
H13C H 0.0701 0.5690 0.5363 0.077 Uiso 1 1 calc R . .
C14 C 0.3432(3) 0.5963(10) 0.7414(3) 0.0489(13) Uani 1 1 d . . .
H14A H 0.3376 0.7508 0.7298 0.073 Uiso 1 1 calc R . .
H14B H 0.3855 0.5456 0.7392 0.073 Uiso 1 1 calc R . .
H14C H 0.3454 0.5712 0.7927 0.073 Uiso 1 1 calc R . .
N1 N 0.0000 0.1445(8) 0.2500 0.0291(11) Uani 1 2 d S . .
O1 O 0.0248(2) -0.0543(5) 0.38995(19) 0.0434(9) Uani 1 1 d . . .
O2 O 0.08797(17) 0.2356(5) 0.44703(17) 0.0362(8) Uani 1 1 d . . .
 
loop_
 _atom_site_aniso_label
 _atom_site_aniso_U_11
 _atom_site_aniso_U_22
 _atom_site_aniso_U_33
 _atom_site_aniso_U_23
 _atom_site_aniso_U_13
 _atom_site_aniso_U_12
C1 0.031(2) 0.027(2) 0.027(2) -0.0010(15) 0.0097(17) -0.0003(15)
C2 0.031(2) 0.027(2) 0.032(2) -0.0047(16) 0.0100(17) -0.0008(16)
C3 0.035(3) 0.020(3) 0.038(3) 0.000 0.013(3) 0.000
C4 0.039(2) 0.0211(19) 0.029(2) -0.0015(15) 0.0126(17) -0.0013(16)
C5 0.050(3) 0.037(2) 0.026(2) 0.0038(18) 0.0062(19) -0.013(2)
C6 0.044(3) 0.034(2) 0.024(2) 0.0014(16) 0.0122(18) -0.0083(18)
C7 0.031(2) 0.042(2) 0.030(2) -0.0008(17) 0.0117(18) -0.0030(18)
C8 0.037(2) 0.037(2) 0.036(2) -0.0046(18) 0.0168(19) -0.0045(18)
C9 0.036(2) 0.040(2) 0.029(2) -0.0055(18) 0.0110(18) -0.0056(18)
C10 0.038(2) 0.039(2) 0.032(2) 0.0012(18) 0.0148(18) 0.0021(18)
C11 0.049(3) 0.029(2) 0.025(2) 0.0020(16) 0.0171(19) -0.0007(18)
C12 0.068(3) 0.036(2) 0.041(3) -0.003(2) 0.026(2) 0.001(2)
C13 0.034(3) 0.057(3) 0.059(3) 0.000(3) 0.015(2) 0.002(2)
C14 0.040(3) 0.057(3) 0.043(3) -0.016(2) 0.011(2) -0.009(2)
N1 0.032(2) 0.025(2) 0.027(2) 0.000 0.009(2) 0.000
O1 0.062(2) 0.0300(17) 0.0300(16) -0.0005(12) 0.0105(15) -0.0092(15)
O2 0.0463(18) 0.0308(16) 0.0233(15) -0.0009(11) 0.0062(13) -0.0116(13)
 
_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
C1 N1 1.334(5) . ?
C1 C2 1.389(6) . ?
C1 C4 1.514(6) . ?
C2 C3 1.385(5) . ?
C2 H2 0.9500 . ?
C3 C2 1.385(5) 2 ?
C3 H3 0.9500 . ?
C4 O1 1.192(5) . ?
C4 O2 1.339(5) . ?
C5 O2 1.464(5) . ?
C5 C6 1.497(6) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C11 1.400(7) . ?
C6 C7 1.408(7) . ?
C7 C8 1.393(6) . ?
C7 C13 1.508(7) . ?
C8 C9 1.376(7) . ?
C8 H8 0.9500 . ?
C9 C10 1.387(7) . ?
C9 C14 1.507(6) . ?
C10 C11 1.398(7) . ?
C10 H10 0.9500 . ?
C11 C12 1.514(6) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
N1 C1 1.334(5) 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
N1 C1 C2 124.1(4) . . ?
N1 C1 C4 114.8(4) . . ?
C2 C1 C4 121.1(4) . . ?
C3 C2 C1 118.6(4) . . ?
C3 C2 H2 120.7 . . ?
C1 C2 H2 120.7 . . ?
C2 C3 C2 118.3(5) 2 . ?
C2 C3 H3 120.9 2 . ?
C2 C3 H3 120.9 . . ?
O1 C4 O2 125.0(4) . . ?
O1 C4 C1 124.7(4) . . ?
O2 C4 C1 110.2(3) . . ?
O2 C5 C6 107.8(3) . . ?
O2 C5 H5A 110.1 . . ?
C6 C5 H5A 110.2 . . ?
O2 C5 H5B 110.1 . . ?
C6 C5 H5B 110.2 . . ?
H5A C5 H5B 108.5 . . ?
C11 C6 C7 119.9(4) . . ?
C11 C6 C5 120.6(4) . . ?
C7 C6 C5 119.5(4) . . ?
C8 C7 C6 119.0(4) . . ?
C8 C7 C13 119.6(4) . . ?
C6 C7 C13 121.4(4) . . ?
C9 C8 C7 122.0(4) . . ?
C9 C8 H8 119.0 . . ?
C7 C8 H8 119.0 . . ?
C8 C9 C10 118.3(4) . . ?
C8 C9 C14 121.0(4) . . ?
C10 C9 C14 120.7(4) . . ?
C9 C10 C11 122.0(4) . . ?
C9 C10 H10 119.0 . . ?
C11 C10 H10 119.0 . . ?
C10 C11 C6 118.7(4) . . ?
C10 C11 C12 118.6(5) . . ?
C6 C11 C12 122.7(4) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C7 C13 H13A 109.5 . . ?
C7 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C7 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C9 C14 H14A 109.5 . . ?
C9 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C9 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C1 N1 C1 116.3(5) . 2 ?
C4 O2 C5 115.4(3) . . ?
 
_diffrn_measured_fraction_theta_max    0.934
_diffrn_reflns_theta_full              27.49
_diffrn_measured_fraction_theta_full   0.934
_refine_diff_density_max    0.462
_refine_diff_density_min   -0.497
_refine_diff_density_rms    0.092
