 
data_0527nm 
 
_audit_creation_method            SHELXL-97 
_chemical_name_systematic 
; 
 ? 
; 
_chemical_name_common             ?
_chemical_absolute_configuration syn 
_chemical_melting_point           ? 
_chemical_formula_moiety          ? 
_chemical_formula_sum 
 'C18 H33 N O4' 
_chemical_formula_weight          327.45 
 
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' 
 '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' 
 'H'  'H'   0.0000   0.0000 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 
_symmetry_cell_setting            'orthorhombic'
_symmetry_space_group_name_H-M    'P2(1)2(1)2(1)' 
 
loop_ 
 _symmetry_equiv_pos_as_xyz 
 'x, y, z' 
 '-x+1/2, -y, z+1/2' 
 '-x, y+1/2, -z+1/2' 
 'x+1/2, -y+1/2, -z' 
 
_cell_length_a                    8.6977(9) 
_cell_length_b                    12.5877(13) 
_cell_length_c                    18.8825(19) 
_cell_angle_alpha                 90.00 
_cell_angle_beta                  90.00 
_cell_angle_gamma                 90.00 
_cell_volume                      2067.3(4) 
_cell_formula_units_Z             4 
_cell_measurement_temperature     298(2) 
_cell_measurement_reflns_used     ? 
_cell_measurement_theta_min       ? 
_cell_measurement_theta_max       ? 
 
_exptl_crystal_description        'block' 
_exptl_crystal_colour             'colorless' 
_exptl_crystal_size_max           0.46 
_exptl_crystal_size_mid           0.38 
_exptl_crystal_size_min           0.28 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_diffrn     1.052 
_exptl_crystal_density_method     'not measured' 
_exptl_crystal_F_000              720 
_exptl_absorpt_coefficient_mu     0.073 
_exptl_absorpt_correction_type    'multi-scan' 
_exptl_absorpt_correction_T_min   0.9672 
_exptl_absorpt_correction_T_max   0.9799 
_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   'Bruker Apex II' 
_diffrn_measurement_method        'Phi-Omega scan' 
_diffrn_detector_area_resol_mean  3 
_diffrn_standards_number          ? 
_diffrn_standards_interval_count  ? 
_diffrn_standards_interval_time   ? 
_diffrn_standards_decay_%         ? 
_diffrn_reflns_number             8622 
_diffrn_reflns_av_R_equivalents   0.0368 
_diffrn_reflns_av_sigmaI/netI     0.0374 
_diffrn_reflns_limit_h_min        -10 
_diffrn_reflns_limit_h_max        10 
_diffrn_reflns_limit_k_min        -14 
_diffrn_reflns_limit_k_max        9 
_diffrn_reflns_limit_l_min        -17 
_diffrn_reflns_limit_l_max        22 
_diffrn_reflns_theta_min          1.94 
_diffrn_reflns_theta_max          25.00 
_reflns_number_total              3609 
_reflns_number_gt                 3015 
_reflns_threshold_expression      >2sigma(I) 
 
_computing_data_collection        'Bruker Apex II'  
_computing_cell_refinement        'Bruker Apex II'  
_computing_data_reduction         'SAINT' 
_computing_structure_solution     'SHELXS-97 (Sheldrick, 1990)' 
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 1997)' 
_computing_molecular_graphics     'Mercury 2.3' 
_computing_publication_material   'Shelxl-97'
 
_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)+(0.1594P)²+0.1144P] where P=(Fo²+2Fc²)/3' 
_atom_sites_solution_primary      direct 
_atom_sites_solution_secondary    difmap 
_atom_sites_solution_hydrogens    geom 
_refine_ls_hydrogen_treatment     constr 
_refine_ls_extinction_method      none 
_refine_ls_extinction_coef        ? 
_refine_ls_abs_structure_details 
 'Flack H D (1983), Acta Cryst. A39, 876-881' 
_refine_ls_abs_structure_Flack    -1(2) 
_refine_ls_number_reflns          3609 
_refine_ls_number_parameters      204 
_refine_ls_number_restraints      0 
_refine_ls_R_factor_all           0.0820 
_refine_ls_R_factor_gt            0.0724 
_refine_ls_wR_factor_ref          0.2230 
_refine_ls_wR_factor_gt           0.2043 
_refine_ls_goodness_of_fit_ref    1.090 
_refine_ls_restrained_S_all       1.090 
_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 
O1 O 0.1469(2) 0.78637(19) 0.08297(11) 0.0748(6) Uani 1 1 d . . . 
O2 O -0.0827(2) 0.71812(15) 0.10120(10) 0.0647(5) Uani 1 1 d . . . 
C3 C 0.0459(3) 0.7525(2) 0.12358(13) 0.0559(6) Uani 1 1 d . . . 
C4 C 0.0691(3) 0.7556(2) 0.20342(13) 0.0605(6) Uani 1 1 d . . . 
H4 H 0.0260 0.6898 0.2228 0.073 Uiso 1 1 calc R . . 
C5 C 0.2352(4) 0.7622(4) 0.22764(18) 0.0869(11) Uani 1 1 d . . . 
H5A H 0.3011 0.7815 0.1883 0.104 Uiso 1 1 calc R . . 
H5B H 0.2688 0.6941 0.2460 0.104 Uiso 1 1 calc R . . 
C6 C 0.2438(4) 0.8464(3) 0.2853(2) 0.0853(10) Uani 1 1 d . . . 
H6A H 0.2859 0.9121 0.2666 0.102 Uiso 1 1 calc R . . 
H6B H 0.3078 0.8225 0.3242 0.102 Uiso 1 1 calc R . . 
C7 C 0.0760(4) 0.8627(2) 0.31013(14) 0.0651(7) Uani 1 1 d . . . 
C8 C 0.0448(4) 0.9710(2) 0.34343(14) 0.0682(7) Uani 1 1 d . . . 
O9 O 0.1611(3) 1.03594(18) 0.34298(13) 0.0758(6) Uani 1 1 d . . . 
H9 H 0.1344 1.0935 0.3592 0.114 Uiso 1 1 calc R . . 
O10 O -0.0780(3) 0.9951(2) 0.36694(18) 0.1063(10) Uani 1 1 d . . . 
C11 C 0.0331(7) 0.7797(3) 0.36538(19) 0.1123(16) Uani 1 1 d . . . 
H11A H 0.0937 0.7904 0.4073 0.168 Uiso 1 1 calc R . . 
H11B H 0.0526 0.7100 0.3468 0.168 Uiso 1 1 calc R . . 
H11C H -0.0740 0.7863 0.3769 0.168 Uiso 1 1 calc R . . 
C12 C -0.0176(3) 0.8499(2) 0.23901(14) 0.0614(7) Uani 1 1 d . . . 
C13 C -0.0023(5) 0.9513(3) 0.19518(16) 0.0819(10) Uani 1 1 d . . . 
H13A H -0.0407 0.9388 0.1482 0.123 Uiso 1 1 calc R . . 
H13B H 0.1039 0.9716 0.1927 0.123 Uiso 1 1 calc R . . 
H13C H -0.0606 1.0072 0.2170 0.123 Uiso 1 1 calc R . . 
C14 C -0.1873(5) 0.8240(4) 0.2514(2) 0.1082(15) Uani 1 1 d . . . 
H14A H -0.2366 0.8832 0.2740 0.162 Uiso 1 1 calc R . . 
H14B H -0.1954 0.7625 0.2812 0.162 Uiso 1 1 calc R . . 
H14C H -0.2363 0.8100 0.2068 0.162 Uiso 1 1 calc R . . 
C20 C 0.4663(8) 0.9530(4) 0.0547(3) 0.1289(18) Uani 1 1 d . . . 
N1A N 0.4503(8) 0.7736(6) 0.0479(3) 0.062(2) Uiso 0.53 1 d P A 1 
C15A C 0.5005(9) 0.6386(8) 0.0667(4) 0.069(2) Uiso 0.53 1 d P A 1 
C16A C 0.4224(13) 0.5777(9) 0.0447(6) 0.086(3) Uiso 0.53 1 d P A 1 
C17A C 0.4496(16) 0.4453(11) 0.0497(8) 0.117(4) Uiso 0.53 1 d P A 1 
C18A C 0.5889(13) 0.4141(8) 0.0159(6) 0.121(3) Uiso 0.53 1 d P A 1 
C19A C 0.5420(10) 0.8353(8) 0.0813(5) 0.081(3) Uiso 0.53 1 d P A 1 
C21A C 0.5468(13) 1.0377(10) 0.1037(7) 0.116(3) Uiso 0.53 1 d P A 1 
C22A C 0.479(2) 1.0814(14) 0.1539(10) 0.178(6) Uiso 0.53 1 d P A 1 
N1B N 0.4494(7) 0.7466(6) 0.0480(3) 0.0534(19) Uiso 0.47 1 d P A 2 
C15B C 0.5174(9) 0.6699(8) 0.0732(4) 0.067(2) Uiso 0.47 1 d P A 2 
C16B C 0.3995(12) 0.5566(9) 0.0351(6) 0.077(3) Uiso 0.47 1 d P A 2 
C17B C 0.4763(15) 0.4661(10) 0.0713(7) 0.106(4) Uiso 0.47 1 d P A 2 
C18B C 0.3921(19) 0.3788(14) 0.0336(8) 0.144(4) Uiso 0.47 1 d P A 2 
C19B C 0.5316(11) 0.8644(9) 0.0715(5) 0.076(3) Uiso 0.47 1 d P A 2 
C21B C 0.529(2) 1.0652(16) 0.0742(11) 0.154(6) Uiso 0.47 1 d P A 2 
C22B C 0.457(2) 1.1384(17) 0.1016(11) 0.179(6) Uiso 0.47 1 d P A 2 
 
 
_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 C3 1.241(3) . ? 
O2 C3 1.272(3) . ? 
C3 C4 1.521(3) . ? 
C4 C5 1.518(4) . ? 
C4 C12 1.560(4) . ? 
C4 H4 0.9800 . ? 
C5 C6 1.521(5) . ? 
C5 H5A 0.9700 . ? 
C5 H5B 0.9700 . ? 
C6 C7 1.547(5) . ? 
C6 H6A 0.9700 . ? 
C6 H6B 0.9700 . ? 
C7 C11 1.523(5) . ? 
C7 C8 1.525(4) . ? 
C7 C12 1.579(4) . ? 
C8 O10 1.197(4) . ? 
C8 O9 1.300(4) . ? 
O9 H9 0.8200 . ? 
C11 H11A 0.9600 . ? 
C11 H11B 0.9600 . ? 
C11 H11C 0.9600 . ? 
C12 C13 1.527(4) . ? 
C12 C14 1.529(5) . ? 
C13 H13A 0.9600 . ? 
C13 H13B 0.9600 . ? 
C13 H13C 0.9600 . ? 
C14 H14A 0.9600 . ? 
C14 H14B 0.9600 . ? 
C14 H14C 0.9600 . ? 
C20 C19B 1.291(13) . ? 
C20 C21B 1.557(19) . ? 
C20 C21A 1.576(13) . ? 
C20 C19A 1.698(12) . ? 
N1A C19A 1.279(11) . ? 
N1A C15A 1.790(11) . ? 
C15A C16A 1.105(12) . ? 
C16A C17A 1.686(17) . ? 
C17A C18A 1.425(17) . ? 
C21A C22A 1.246(19) . ? 
N1B C15B 1.229(10) . ? 
N1B C19B 1.706(12) . ? 
C15B C16B 1.899(15) . ? 
C16B C17B 1.487(16) . ? 
C17B C18B 1.50(2) . ? 
C21B C22B 1.22(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 
O1 C3 O2 122.3(2) . . ? 
O1 C3 C4 120.6(3) . . ? 
O2 C3 C4 117.0(2) . . ? 
C5 C4 C3 115.2(2) . . ? 
C5 C4 C12 106.8(2) . . ? 
C3 C4 C12 112.5(2) . . ? 
C5 C4 H4 107.3 . . ? 
C3 C4 H4 107.3 . . ? 
C12 C4 H4 107.3 . . ? 
C4 C5 C6 107.5(3) . . ? 
C4 C5 H5A 110.2 . . ? 
C6 C5 H5A 110.2 . . ? 
C4 C5 H5B 110.2 . . ? 
C6 C5 H5B 110.2 . . ? 
H5A C5 H5B 108.5 . . ? 
C5 C6 C7 105.3(3) . . ? 
C5 C6 H6A 110.7 . . ? 
C7 C6 H6A 110.7 . . ? 
C5 C6 H6B 110.7 . . ? 
C7 C6 H6B 110.7 . . ? 
H6A C6 H6B 108.8 . . ? 
C11 C7 C8 106.7(3) . . ? 
C11 C7 C6 110.4(3) . . ? 
C8 C7 C6 114.3(3) . . ? 
C11 C7 C12 112.7(3) . . ? 
C8 C7 C12 110.5(2) . . ? 
C6 C7 C12 102.4(2) . . ? 
O10 C8 O9 122.5(3) . . ? 
O10 C8 C7 122.6(3) . . ? 
O9 C8 C7 114.9(3) . . ? 
C8 O9 H9 109.5 . . ? 
C7 C11 H11A 109.5 . . ? 
C7 C11 H11B 109.5 . . ? 
H11A C11 H11B 109.5 . . ? 
C7 C11 H11C 109.5 . . ? 
H11A C11 H11C 109.5 . . ? 
H11B C11 H11C 109.5 . . ? 
C13 C12 C14 110.2(3) . . ? 
C13 C12 C4 111.2(2) . . ? 
C14 C12 C4 111.7(3) . . ? 
C13 C12 C7 109.3(3) . . ? 
C14 C12 C7 112.9(3) . . ? 
C4 C12 C7 101.2(2) . . ? 
C12 C13 H13A 109.5 . . ? 
C12 C13 H13B 109.5 . . ? 
H13A C13 H13B 109.5 . . ? 
C12 C13 H13C 109.5 . . ? 
H13A C13 H13C 109.5 . . ? 
H13B C13 H13C 109.5 . . ? 
C12 C14 H14A 109.5 . . ? 
C12 C14 H14B 109.5 . . ? 
H14A C14 H14B 109.5 . . ? 
C12 C14 H14C 109.5 . . ? 
H14A C14 H14C 109.5 . . ? 
H14B C14 H14C 109.5 . . ? 
C19B C20 C21B 124.9(10) . . ? 
C19B C20 C21A 104.1(8) . . ? 
C21B C20 C21A 24.9(7) . . ? 
C19B C20 C19A 4.2(6) . . ? 
C21B C20 C19A 125.9(10) . . ? 
C21A C20 C19A 104.1(7) . . ? 
C19A N1A C15A 109.1(7) . . ? 
C16A C15A N1A 115.8(7) . . ? 
C15A C16A C17A 125.3(11) . . ? 
C18A C17A C16A 111.5(10) . . ? 
N1A C19A C20 98.2(7) . . ? 
C22A C21A C20 122.3(12) . . ? 
C15B N1B C19B 112.4(7) . . ? 
N1B C15B C16B 100.5(7) . . ? 
C17B C16B C15B 99.1(9) . . ? 
C16B C17B C18B 97.1(11) . . ? 
C20 C19B N1B 120.2(7) . . ? 
C22B C21B C20 127.4(19) . . ? 
 
loop_ 
 _geom_hbond_atom_site_label_D 
 _geom_hbond_atom_site_label_H 
 _geom_hbond_atom_site_label_A 
 _geom_hbond_distance_DH 
 _geom_hbond_distance_HA 
 _geom_hbond_distance_DA 
 _geom_hbond_angle_DHA 
 _geom_hbond_site_symmetry_A 
O9 H9 O2  0.82 1.80 2.614(3) 176.9 3 
 
_diffrn_measured_fraction_theta_max    1.000 
_diffrn_reflns_theta_full              25.00 
_diffrn_measured_fraction_theta_full   1.000 
_refine_diff_density_max    0.365 
_refine_diff_density_min   -0.265 
_refine_diff_density_rms    0.084 
