# ja010489b.cif data_rei02 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C30 H48 Li2 N2 O2' _chemical_formula_weight 482.58 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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.8594(9) _cell_length_b 9.8398(10) _cell_length_c 10.4018(11) _cell_angle_alpha 117.115(2) _cell_angle_beta 102.521(2) _cell_angle_gamma 98.701(2) _cell_volume 754.58(13) _cell_formula_units_Z 1 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.21 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.062 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 264 _exptl_absorpt_coefficient_mu 0.064 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9736 _exptl_absorpt_correction_T_max 0.9867 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 3067 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0322 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.33 _diffrn_reflns_theta_max 26.43 _reflns_number_total 3067 _reflns_number_gt 2120 _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 F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ 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/[\s^2^(Fo^2^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/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 3067 _refine_ls_number_parameters 166 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0742 _refine_ls_R_factor_gt 0.0524 _refine_ls_wR_factor_ref 0.1616 _refine_ls_wR_factor_gt 0.1497 _refine_ls_goodness_of_fit_ref 1.013 _refine_ls_restrained_S_all 1.013 _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 0.18600(14) -0.22809(13) -0.06532(13) 0.0534(4) Uani 1 1 d . . . N1 N 0.22886(15) 0.06220(14) 0.28224(14) 0.0346(3) Uani 1 1 d . . . Li1 Li 0.0950(3) -0.0602(3) 0.0439(3) 0.0362(6) Uani 1 1 d . . . C1 C 0.3514(2) 0.42659(19) 0.2754(2) 0.0464(4) Uani 1 1 d . . . H1 H 0.3961 0.4949 0.3830 0.056 Uiso 1 1 calc R . . C2 C 0.3898(2) 0.4781(2) 0.1793(2) 0.0558(5) Uani 1 1 d . . . H2 H 0.4577 0.5826 0.2204 0.067 Uiso 1 1 calc R . . C3 C 0.3285(2) 0.3763(2) 0.0245(2) 0.0522(5) Uani 1 1 d . . . H3 H 0.3570 0.4083 -0.0426 0.063 Uiso 1 1 calc R . . C4 C 0.22446(19) 0.2262(2) -0.03375(19) 0.0446(4) Uani 1 1 d . . . H4 H 0.1839 0.1583 -0.1416 0.054 Uiso 1 1 calc R . . C5 C 0.17497(18) 0.16751(17) 0.05528(17) 0.0352(4) Uani 1 1 d . . . C6 C 0.24740(18) 0.27494(17) 0.21469(17) 0.0360(4) Uani 1 1 d . . . C7 C 0.2099(2) 0.22261(18) 0.32355(17) 0.0398(4) Uani 1 1 d . . . H7A H 0.2830 0.3008 0.4285 0.048 Uiso 1 1 calc R . . H7B H 0.0977 0.2214 0.3225 0.048 Uiso 1 1 calc R . . C8 C 0.39734(19) 0.0655(2) 0.2948(2) 0.0460(4) Uani 1 1 d . . . H8A H 0.4289 0.0974 0.2257 0.069 Uiso 1 1 calc R . . H8B H 0.4092 -0.0408 0.2671 0.069 Uiso 1 1 calc R . . H8C H 0.4666 0.1422 0.4001 0.069 Uiso 1 1 calc R . . C9 C 0.1670(2) 0.0005(2) 0.37297(18) 0.0445(4) Uani 1 1 d . . . H9 H 0.0544 0.0091 0.3617 0.053 Uiso 1 1 calc R . . C10 C 0.2601(2) 0.0949(3) 0.5445(2) 0.0600(5) Uani 1 1 d . . . H10A H 0.3716 0.0894 0.5612 0.090 Uiso 1 1 calc R . . H10B H 0.2084 0.0493 0.5959 0.090 Uiso 1 1 calc R . . H10C H 0.2598 0.2065 0.5861 0.090 Uiso 1 1 calc R . . C11 C 0.1546(3) -0.1751(2) 0.3077(2) 0.0624(6) Uani 1 1 d . . . H11A H 0.0971 -0.2330 0.1975 0.094 Uiso 1 1 calc R . . H11B H 0.0956 -0.2174 0.3572 0.094 Uiso 1 1 calc R . . H11C H 0.2633 -0.1883 0.3260 0.094 Uiso 1 1 calc R . . C12 C 0.1104(2) -0.3974(2) -0.1412(2) 0.0547(5) Uani 1 1 d . . . H12A H -0.0045 -0.4193 -0.1471 0.066 Uiso 1 1 calc R . . H12B H 0.1661 -0.4446 -0.0860 0.066 Uiso 1 1 calc R . . C13 C 0.1249(3) -0.4637(3) -0.2970(3) 0.0858(8) Uani 1 1 d . . . H13A H 0.0177 -0.5002 -0.3743 0.103 Uiso 1 1 calc R . . H13B H 0.1695 -0.5556 -0.3214 0.103 Uiso 1 1 calc R . . C14 C 0.2366(2) -0.3322(2) -0.2972(2) 0.0665(6) Uani 1 1 d . . . H14A H 0.1765 -0.2921 -0.3577 0.080 Uiso 1 1 calc R . . H14B H 0.3220 -0.3694 -0.3394 0.080 Uiso 1 1 calc R . . C15 C 0.3076(2) -0.2051(2) -0.1306(2) 0.0629(6) Uani 1 1 d . . . H15A H 0.4090 -0.2183 -0.0818 0.075 Uiso 1 1 calc R . . H15B H 0.3304 -0.0974 -0.1183 0.075 Uiso 1 1 calc R . . 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 O1 0.0516(8) 0.0400(7) 0.0529(8) 0.0093(6) 0.0218(6) 0.0125(5) N1 0.0338(7) 0.0369(7) 0.0330(7) 0.0185(6) 0.0101(5) 0.0089(5) Li1 0.0354(14) 0.0329(13) 0.0353(14) 0.0149(11) 0.0099(11) 0.0065(11) C1 0.0448(10) 0.0337(9) 0.0433(10) 0.0139(8) 0.0014(8) 0.0025(7) C2 0.0426(10) 0.0394(10) 0.0751(14) 0.0332(10) 0.0011(9) -0.0032(8) C3 0.0406(10) 0.0614(12) 0.0646(12) 0.0457(10) 0.0110(9) 0.0035(8) C4 0.0366(9) 0.0512(10) 0.0417(9) 0.0250(8) 0.0077(7) 0.0030(8) C5 0.0328(8) 0.0339(8) 0.0347(8) 0.0161(7) 0.0089(6) 0.0055(6) C6 0.0338(8) 0.0309(8) 0.0387(9) 0.0153(7) 0.0089(7) 0.0088(6) C7 0.0444(9) 0.0362(9) 0.0311(8) 0.0118(7) 0.0113(7) 0.0107(7) C8 0.0375(9) 0.0529(10) 0.0482(10) 0.0269(9) 0.0118(8) 0.0136(8) C9 0.0405(9) 0.0548(11) 0.0406(9) 0.0288(8) 0.0114(7) 0.0068(8) C10 0.0654(13) 0.0735(13) 0.0414(10) 0.0336(10) 0.0138(9) 0.0111(10) C11 0.0718(14) 0.0533(12) 0.0637(13) 0.0384(10) 0.0131(10) 0.0058(10) C12 0.0651(12) 0.0393(10) 0.0590(12) 0.0224(9) 0.0192(10) 0.0223(9) C13 0.113(2) 0.0498(13) 0.0638(14) 0.0059(11) 0.0408(14) 0.0024(12) C14 0.0590(13) 0.0631(13) 0.0600(13) 0.0166(10) 0.0258(10) 0.0115(10) C15 0.0461(11) 0.0522(11) 0.0675(13) 0.0103(10) 0.0254(10) 0.0111(9) _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 C15 1.434(2) . ? O1 C12 1.442(2) . ? O1 Li1 1.939(3) . ? N1 C8 1.4638(19) . ? N1 C7 1.4824(19) . ? N1 C9 1.4849(19) . ? N1 Li1 2.139(3) . ? Li1 C5 2.186(3) . ? Li1 C5 2.252(3) 2 ? Li1 Li1 2.449(5) 2 ? Li1 C7 2.779(3) . ? C1 C2 1.389(3) . ? C1 C6 1.395(2) . ? C2 C3 1.370(3) . ? C3 C4 1.389(2) . ? C4 C5 1.403(2) . ? C5 C6 1.419(2) . ? C5 Li1 2.252(3) 2 ? C6 C7 1.517(2) . ? C9 C11 1.517(2) . ? C9 C10 1.532(2) . ? C12 C13 1.490(3) . ? C13 C14 1.507(3) . ? C14 C15 1.509(3) . ? 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 C15 O1 C12 107.35(13) . . ? C15 O1 Li1 122.60(13) . . ? C12 O1 Li1 126.40(13) . . ? C8 N1 C7 109.75(12) . . ? C8 N1 C9 112.80(12) . . ? C7 N1 C9 111.85(12) . . ? C8 N1 Li1 106.94(12) . . ? C7 N1 Li1 98.62(11) . . ? C9 N1 Li1 115.89(11) . . ? O1 Li1 N1 109.03(13) . . ? O1 Li1 C5 117.50(13) . . ? N1 Li1 C5 86.39(10) . . ? O1 Li1 C5 106.14(12) . 2 ? N1 Li1 C5 124.53(13) . 2 ? C5 Li1 C5 113.05(11) . 2 ? O1 Li1 Li1 131.91(18) . 2 ? N1 Li1 Li1 117.72(16) . 2 ? C5 Li1 Li1 57.81(11) . 2 ? C5 Li1 Li1 55.24(10) 2 2 ? O1 Li1 C7 134.74(12) . . ? N1 Li1 C7 31.83(6) . . ? C5 Li1 C7 59.70(8) . . ? C5 Li1 C7 116.17(11) 2 . ? Li1 Li1 C7 87.43(13) 2 . ? C2 C1 C6 120.29(15) . . ? C3 C2 C1 119.18(15) . . ? C2 C3 C4 119.63(16) . . ? C3 C4 C5 124.67(16) . . ? C4 C5 C6 113.34(13) . . ? C4 C5 Li1 139.40(13) . . ? C6 C5 Li1 102.42(12) . . ? C4 C5 Li1 108.06(12) . 2 ? C6 C5 Li1 119.58(12) . 2 ? Li1 C5 Li1 66.95(11) . 2 ? C1 C6 C5 122.80(14) . . ? C1 C6 C7 118.65(13) . . ? C5 C6 C7 118.55(13) . . ? N1 C7 C6 112.10(12) . . ? N1 C7 Li1 49.55(8) . . ? C6 C7 Li1 77.01(9) . . ? N1 C9 C11 111.11(14) . . ? N1 C9 C10 114.92(13) . . ? C11 C9 C10 110.66(15) . . ? O1 C12 C13 105.33(16) . . ? C12 C13 C14 107.12(17) . . ? C13 C14 C15 103.60(18) . . ? O1 C15 C14 104.59(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 C15 O1 Li1 N1 -92.78(18) . . . . ? C12 O1 Li1 N1 111.54(16) . . . . ? C15 O1 Li1 C5 3.2(2) . . . . ? C12 O1 Li1 C5 -152.46(14) . . . . ? C15 O1 Li1 C5 130.83(15) . . . 2 ? C12 O1 Li1 C5 -24.9(2) . . . 2 ? C15 O1 Li1 Li1 73.4(3) . . . 2 ? C12 O1 Li1 Li1 -82.3(3) . . . 2 ? C15 O1 Li1 C7 -70.2(2) . . . . ? C12 O1 Li1 C7 134.08(17) . . . . ? C8 N1 Li1 O1 35.11(16) . . . . ? C7 N1 Li1 O1 148.91(12) . . . . ? C9 N1 Li1 O1 -91.62(15) . . . . ? C8 N1 Li1 C5 -82.77(12) . . . . ? C7 N1 Li1 C5 31.02(11) . . . . ? C9 N1 Li1 C5 150.50(11) . . . . ? C8 N1 Li1 C5 161.58(14) . . . 2 ? C7 N1 Li1 C5 -84.63(16) . . . 2 ? C9 N1 Li1 C5 34.8(2) . . . 2 ? C8 N1 Li1 Li1 -133.27(17) . . . 2 ? C7 N1 Li1 Li1 -19.5(2) . . . 2 ? C9 N1 Li1 Li1 100.00(19) . . . 2 ? C8 N1 Li1 C7 -113.79(14) . . . . ? C9 N1 Li1 C7 119.48(15) . . . . ? C6 C1 C2 C3 -2.1(3) . . . . ? C1 C2 C3 C4 2.5(3) . . . . ? C2 C3 C4 C5 0.0(3) . . . . ? C3 C4 C5 C6 -2.5(2) . . . . ? C3 C4 C5 Li1 -152.23(18) . . . . ? C3 C4 C5 Li1 132.39(17) . . . 2 ? O1 Li1 C5 C4 33.0(3) . . . . ? N1 Li1 C5 C4 142.59(18) . . . . ? C5 Li1 C5 C4 -91.2(2) 2 . . . ? Li1 Li1 C5 C4 -91.2(2) 2 . . . ? C7 Li1 C5 C4 160.9(2) . . . . ? O1 Li1 C5 C6 -118.68(15) . . . . ? N1 Li1 C5 C6 -9.08(12) . . . . ? C5 Li1 C5 C6 117.11(14) 2 . . . ? Li1 Li1 C5 C6 117.11(14) 2 . . . ? C7 Li1 C5 C6 9.27(9) . . . . ? O1 Li1 C5 Li1 124.21(19) . . . 2 ? N1 Li1 C5 Li1 -126.19(15) . . . 2 ? C5 Li1 C5 Li1 0.0 2 . . 2 ? C7 Li1 C5 Li1 -107.84(12) . . . 2 ? C2 C1 C6 C5 -0.7(3) . . . . ? C2 C1 C6 C7 179.38(15) . . . . ? C4 C5 C6 C1 2.9(2) . . . . ? Li1 C5 C6 C1 163.22(15) . . . . ? Li1 C5 C6 C1 -126.41(16) 2 . . . ? C4 C5 C6 C7 -177.21(13) . . . . ? Li1 C5 C6 C7 -16.86(16) . . . . ? Li1 C5 C6 C7 53.50(18) 2 . . . ? C8 N1 C7 C6 63.24(16) . . . . ? C9 N1 C7 C6 -170.77(12) . . . . ? Li1 N1 C7 C6 -48.32(14) . . . . ? C8 N1 C7 Li1 111.56(14) . . . . ? C9 N1 C7 Li1 -122.46(14) . . . . ? C1 C6 C7 N1 -131.18(15) . . . . ? C5 C6 C7 N1 48.90(18) . . . . ? C1 C6 C7 Li1 -166.86(15) . . . . ? C5 C6 C7 Li1 13.22(13) . . . . ? O1 Li1 C7 N1 -43.42(17) . . . . ? C5 Li1 C7 N1 -143.44(13) . . . . ? C5 Li1 C7 N1 113.96(15) 2 . . . ? Li1 Li1 C7 N1 162.81(18) 2 . . . ? O1 Li1 C7 C6 91.33(18) . . . . ? N1 Li1 C7 C6 134.75(14) . . . . ? C5 Li1 C7 C6 -8.69(9) . . . . ? C5 Li1 C7 C6 -111.29(13) 2 . . . ? Li1 Li1 C7 C6 -62.43(13) 2 . . . ? C8 N1 C9 C11 -67.59(18) . . . . ? C7 N1 C9 C11 168.11(14) . . . . ? Li1 N1 C9 C11 56.14(18) . . . . ? C8 N1 C9 C10 59.01(19) . . . . ? C7 N1 C9 C10 -65.28(18) . . . . ? Li1 N1 C9 C10 -177.26(14) . . . . ? C15 O1 C12 C13 -28.8(2) . . . . ? Li1 O1 C12 C13 129.92(19) . . . . ? O1 C12 C13 C14 10.0(3) . . . . ? C12 C13 C14 C15 11.0(3) . . . . ? C12 O1 C15 C14 36.0(2) . . . . ? Li1 O1 C15 C14 -123.65(17) . . . . ? C13 C14 C15 O1 -28.2(2) . . . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 26.43 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.243 _refine_diff_density_min -0.156 _refine_diff_density_rms 0.038 #===END