data_e:\crysta~1\aw1116\jo\aw1116 
 
_audit_creation_method            SHELXL-97 
_chemical_name_systematic 
; 
 ? 
; 
_chemical_name_common             ? 
_chemical_melting_point           ? 
_chemical_formula_moiety           'C22 H38 Li N O4'  
_chemical_formula_sum 
 'C22 H38 Li N O4' 
_chemical_formula_weight          387.47 
 
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' 
 'Li'  'Li'  -0.0003   0.0001 
 '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    	'P 21/n '
_symmetry_space_group_name_Hall    '-P 2yn'

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                    7.8821(16) 
_cell_length_b                    18.975(4) 
_cell_length_c                    15.737(3) 
_cell_angle_alpha                 90.00 
_cell_angle_beta                  92.84(3) 
_cell_angle_gamma                 90.00 
_cell_volume                      2350.8(8) 
_cell_formula_units_Z             4 
_cell_measurement_temperature     173(2) 
_cell_measurement_reflns_used     19121 
_cell_measurement_theta_min       1
_cell_measurement_theta_max       25.35
 
_exptl_crystal_description        block 
_exptl_crystal_colour             red
_exptl_crystal_size_max           0.28
_exptl_crystal_size_mid           0.12
_exptl_crystal_size_min           0.07
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_diffrn     1.095 
_exptl_crystal_density_method     'not measured' 
_exptl_crystal_F_000              848 
_exptl_absorpt_coefficient_mu     0.073 
_exptl_absorpt_correction_type 'multi-scan' 
_exptl_absorpt_correction_T_min  0.882
_exptl_absorpt_correction_T_max  1.004
_exptl_absorpt_process_details
;
multi-scan from symmetry-related measurements 
 Sortav (Blessing 1995)
;

 
_diffrn_ambient_temperature       173(2) 
_diffrn_radiation_wavelength      0.71073 
_diffrn_radiation_type            MoK\a 
_diffrn_radiation_source          'fine-focus sealed tube' 
_diffrn_measurement_device_type   'Nonius Kappa CCD'
_diffrn_measurement_method        'Thin slice ω and φ scans'
_diffrn_reflns_number             13765 
_diffrn_reflns_av_R_equivalents   0.0425 
_diffrn_reflns_av_sigmaI/netI     0.0472 
_diffrn_reflns_limit_h_min        -9 
_diffrn_reflns_limit_h_max        9 
_diffrn_reflns_limit_k_min        -22 
_diffrn_reflns_limit_k_max        22 
_diffrn_reflns_limit_l_min        -17 
_diffrn_reflns_limit_l_max        18 
_diffrn_reflns_theta_min          3.14 
_diffrn_reflns_theta_max          25.31 
_reflns_number_total              4238 
_reflns_number_gt                 2961 
_reflns_threshold_expression      >2sigma(I) 
 
_computing_data_collection        'Collect (Nonius B.V. 1998)'
_computing_cell_refinement        'HKL Scalepack (Otwinowski & Minor 1997)' 
_computing_data_reduction
;
 HKL Denzo and Scalepack (Otwinowski & Minor 1997)
;
_computing_structure_solution     'SIR-92 (Altomare et al. 1994)'
_computing_structure_refinement   'SHELXL-97 (Sheldrick 1997)' 
_computing_publication_material   'SHELXL-97 (Sheldrick 1997)' 
 
_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)+(0.1255P)²+3.0378P] 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_number_reflns          4238 
_refine_ls_number_parameters      253 
_refine_ls_number_restraints      0 
_refine_ls_R_factor_all           0.1263 
_refine_ls_R_factor_gt            0.0938 
_refine_ls_wR_factor_ref          0.2729 
_refine_ls_wR_factor_gt           0.2489 
_refine_ls_goodness_of_fit_ref    1.040 
_refine_ls_restrained_S_all       1.040 
_refine_ls_shift/su_max           0.010 
_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 0.2399(3) 0.10274(12) 0.33372(14) 0.0462(6) Uani 1 1 d . . . 
N1 N 0.4868(3) 0.15595(15) 0.37572(17) 0.0432(7) Uani 1 1 d . . . 
C7 C 0.3781(4) 0.12906(17) 0.3147(2) 0.0414(8) Uani 1 1 d . . . 
C1 C 0.4186(4) 0.13424(17) 0.2237(2) 0.0411(8) Uani 1 1 d . . . 
C6 C 0.4104(4) 0.07130(18) 0.1717(2) 0.0407(8) Uani 1 1 d . . . 
C5 C 0.4176(4) 0.0852(2) 0.0817(2) 0.0499(9) Uani 1 1 d . . . 
H5A H 0.4086 0.0466 0.0432 0.060 Uiso 1 1 calc R . . 
C4 C 0.4368(5) 0.1514(2) 0.0494(2) 0.0545(9) Uani 1 1 d . . . 
H4A H 0.4430 0.1570 -0.0103 0.065 Uiso 1 1 calc R . . 
C2 C 0.4380(5) 0.2001(2) 0.1879(2) 0.0517(9) Uani 1 1 d . . . 
H2A H 0.4450 0.2399 0.2245 0.062 Uiso 1 1 calc R . . 
C14 C 0.4341(5) 0.1659(2) 0.4627(2) 0.0567(10) Uani 1 1 d . . . 
H14A H 0.5311 0.1898 0.4943 0.068 Uiso 1 1 calc R . . 
C8 C 0.3973(4) 0.00426(19) 0.2043(2) 0.0474(8) Uani 1 1 d . . . 
H8A H 0.3852 -0.0002 0.2638 0.057 Uiso 1 1 calc R . . 
C11 C 0.6668(4) 0.1715(2) 0.3594(2) 0.0567(10) Uani 1 1 d . . . 
H11A H 0.6832 0.1612 0.2980 0.068 Uiso 1 1 calc R . . 
C3 C 0.4477(5) 0.2107(2) 0.1009(2) 0.0574(10) Uani 1 1 d . . . 
H3A H 0.4611 0.2565 0.0778 0.069 Uiso 1 1 calc R . . 
C9 C 0.4006(5) -0.0612(2) 0.1535(3) 0.0622(10) Uani 1 1 d . . . 
H9A H 0.5031 -0.0610 0.1196 0.075 Uiso 1 1 calc R . . 
H9B H 0.3000 -0.0621 0.1133 0.075 Uiso 1 1 calc R . . 
C10 C 0.4013(6) -0.1273(2) 0.2071(3) 0.0760(13) Uani 1 1 d . . . 
H10A H 0.4043 -0.1688 0.1701 0.114 Uiso 1 1 calc R . . 
H10B H 0.2984 -0.1287 0.2396 0.114 Uiso 1 1 calc R . . 
H10C H 0.5016 -0.1274 0.2465 0.114 Uiso 1 1 calc R . . 
O2 O -0.0251(3) 0.13035(14) 0.18279(18) 0.0638(8) Uani 1 1 d . . . 
O3 O -0.0210(3) -0.00334(15) 0.13547(18) 0.0630(8) Uani 1 1 d . . . 
O4 O 0.0087(4) -0.02711(16) 0.30143(19) 0.0751(9) Uani 1 1 d . . . 
C17 C 0.0006(6) 0.2036(2) 0.1937(3) 0.0723(12) Uani 1 1 d . . . 
H17A H -0.0885 0.2294 0.1612 0.108 Uiso 1 1 calc R . . 
H17B H 0.1119 0.2166 0.1734 0.108 Uiso 1 1 calc R . . 
H17C H -0.0037 0.2155 0.2542 0.108 Uiso 1 1 calc R . . 
C21 C -0.1099(6) -0.0694(3) 0.2540(3) 0.0768(13) Uani 1 1 d . . . 
H21A H -0.2267 -0.0531 0.2638 0.092 Uiso 1 1 calc R . . 
H21B H -0.0997 -0.1190 0.2732 0.092 Uiso 1 1 calc R . . 
C18 C -0.1019(6) 0.1133(2) 0.1025(3) 0.0750(13) Uani 1 1 d . . . 
H18A H -0.0212 0.1221 0.0575 0.090 Uiso 1 1 calc R . . 
H18B H -0.2034 0.1431 0.0910 0.090 Uiso 1 1 calc R . . 
C13 C 0.7862(6) 0.1236(3) 0.4115(3) 0.0892(16) Uani 1 1 d . . . 
H13A H 0.7564 0.0743 0.3999 0.134 Uiso 1 1 calc R . . 
H13B H 0.7760 0.1335 0.4722 0.134 Uiso 1 1 calc R . . 
H13C H 0.9034 0.1322 0.3961 0.134 Uiso 1 1 calc R . . 
C12 C 0.7089(7) 0.2491(3) 0.3743(3) 0.0875(16) Uani 1 1 d . . . 
H12A H 0.6308 0.2783 0.3390 0.131 Uiso 1 1 calc R . . 
H12B H 0.8259 0.2582 0.3591 0.131 Uiso 1 1 calc R . . 
H12C H 0.6970 0.2606 0.4344 0.131 Uiso 1 1 calc R . . 
C16 C 0.2847(6) 0.2150(3) 0.4669(4) 0.101(2) Uani 1 1 d . . . 
H16A H 0.3080 0.2585 0.4361 0.151 Uiso 1 1 calc R . . 
H16B H 0.2655 0.2261 0.5265 0.151 Uiso 1 1 calc R . . 
H16C H 0.1832 0.1922 0.4409 0.151 Uiso 1 1 calc R . . 
C20 C -0.0794(11) -0.0652(4) 0.1638(5) 0.152(4) Uani 1 1 d . . . 
H20A H 0.0033 -0.1024 0.1504 0.183 Uiso 1 1 calc R . . 
H20B H -0.1871 -0.0762 0.1314 0.183 Uiso 1 1 calc R . . 
Li1 Li 0.1227(7) 0.0512(3) 0.2366(4) 0.0454(13) Uani 1 1 d . . . 
C15 C 0.4067(8) 0.0967(3) 0.5092(3) 0.0969(18) Uani 1 1 d . . . 
H15A H 0.5067 0.0666 0.5045 0.145 Uiso 1 1 calc R . . 
H15B H 0.3065 0.0728 0.4836 0.145 Uiso 1 1 calc R . . 
H15C H 0.3891 0.1063 0.5693 0.145 Uiso 1 1 calc R . . 
C22 C 0.0439(8) -0.0475(3) 0.3855(3) 0.0859(15) Uani 1 1 d . . . 
H22A H -0.0310 -0.0865 0.3998 0.129 Uiso 1 1 calc R . . 
H22B H 0.0250 -0.0076 0.4234 0.129 Uiso 1 1 calc R . . 
H22C H 0.1626 -0.0628 0.3925 0.129 Uiso 1 1 calc R . . 
C19 C -0.1502(11) 0.0404(3) 0.1020(5) 0.146(4) Uani 1 1 d . . . 
H19A H -0.2521 0.0346 0.1357 0.176 Uiso 1 1 calc R . . 
H19B H -0.1807 0.0258 0.0428 0.176 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 C7 1.249(4) . ? 
O1 Li1 2.001(6) . ? 
N1 C7 1.355(4) . ? 
N1 C14 1.463(4) . ? 
N1 C11 1.484(4) . ? 
C7 C1 1.485(5) . ? 
C7 Li1 2.739(6) . ? 
C1 C2 1.382(5) . ? 
C1 C6 1.448(5) . ? 
C6 C8 1.377(5) . ? 
C6 C5 1.445(5) . ? 
C6 Li1 2.562(6) . ? 
C5 C4 1.365(5) . ? 
C4 C3 1.387(6) . ? 
C2 C3 1.389(5) . ? 
C14 C16 1.506(6) . ? 
C14 C15 1.522(7) . ? 
C8 C9 1.478(5) . ? 
C8 Li1 2.418(6) . ? 
C11 C13 1.519(6) . ? 
C11 C12 1.524(6) . ? 
C9 C10 1.511(6) . ? 
O2 C17 1.414(5) . ? 
O2 C18 1.411(5) . ? 
O2 Li1 2.058(6) . ? 
O3 C20 1.345(7) . ? 
O3 C19 1.396(7) . ? 
O3 Li1 2.170(6) . ? 
O4 C22 1.393(5) . ? 
O4 C21 1.417(5) . ? 
O4 Li1 2.036(6) . ? 
C21 C20 1.454(9) . ? 
C18 C19 1.433(7) . ? 
 
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 
C7 O1 Li1 112.8(3) . . ? 
C7 N1 C14 120.9(3) . . ? 
C7 N1 C11 121.9(3) . . ? 
C14 N1 C11 117.0(3) . . ? 
O1 C7 N1 120.6(3) . . ? 
O1 C7 C1 119.3(3) . . ? 
N1 C7 C1 120.0(3) . . ? 
O1 C7 Li1 42.34(19) . . ? 
N1 C7 Li1 161.1(3) . . ? 
C1 C7 Li1 78.0(2) . . ? 
C2 C1 C6 121.2(3) . . ? 
C2 C1 C7 119.1(3) . . ? 
C6 C1 C7 119.0(3) . . ? 
C8 C6 C5 122.7(3) . . ? 
C8 C6 C1 123.6(3) . . ? 
C5 C6 C1 113.7(3) . . ? 
C8 C6 Li1 68.3(2) . . ? 
C5 C6 Li1 119.8(2) . . ? 
C1 C6 Li1 85.0(2) . . ? 
C4 C5 C6 122.9(3) . . ? 
C5 C4 C3 122.3(3) . . ? 
C1 C2 C3 123.0(4) . . ? 
N1 C14 C16 112.3(4) . . ? 
N1 C14 C15 113.1(3) . . ? 
C16 C14 C15 112.5(4) . . ? 
C6 C8 C9 124.9(3) . . ? 
C6 C8 Li1 79.8(2) . . ? 
C9 C8 Li1 117.6(3) . . ? 
N1 C11 C13 111.1(3) . . ? 
N1 C11 C12 111.6(4) . . ? 
C13 C11 C12 111.7(4) . . ? 
C4 C3 C2 117.0(3) . . ? 
C8 C9 C10 113.3(4) . . ? 
C17 O2 C18 112.8(3) . . ? 
C17 O2 Li1 126.4(3) . . ? 
C18 O2 Li1 114.2(3) . . ? 
C20 O3 C19 112.9(5) . . ? 
C20 O3 Li1 110.4(3) . . ? 
C19 O3 Li1 109.7(3) . . ? 
C22 O4 C21 116.0(4) . . ? 
C22 O4 Li1 127.3(3) . . ? 
C21 O4 Li1 116.5(3) . . ? 
O4 C21 C20 110.3(4) . . ? 
O2 C18 C19 109.2(4) . . ? 
O3 C20 C21 116.5(6) . . ? 
O1 Li1 O4 100.0(3) . . ? 
O1 Li1 O2 100.8(3) . . ? 
O4 Li1 O2 118.9(3) . . ? 
O1 Li1 O3 176.0(3) . . ? 
O4 Li1 O3 78.0(2) . . ? 
O2 Li1 O3 77.4(2) . . ? 
O1 Li1 C8 87.5(2) . . ? 
O4 Li1 C8 105.0(3) . . ? 
O2 Li1 C8 132.6(3) . . ? 
O3 Li1 C8 96.3(2) . . ? 
O1 Li1 C6 81.2(2) . . ? 
O4 Li1 C6 136.9(3) . . ? 
O2 Li1 C6 102.8(3) . . ? 
O3 Li1 C6 102.6(2) . . ? 
C8 Li1 C6 31.95(13) . . ? 
O1 Li1 C7 24.85(11) . . ? 
O4 Li1 C7 120.1(3) . . ? 
O2 Li1 C7 100.3(2) . . ? 
O3 Li1 C7 158.7(3) . . ? 
C8 Li1 C7 69.36(17) . . ? 
C6 Li1 C7 56.84(14) . . ? 
O3 C19 C18 112.5(5) . . ? 
 
_diffrn_measured_fraction_theta_max    0.983 
_diffrn_reflns_theta_full              25.31 
_diffrn_measured_fraction_theta_full   0.983 
_refine_diff_density_max    0.729 
_refine_diff_density_min   -0.616 
_refine_diff_density_rms    0.060 
