data_rw105m _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H24 N2 O8' _chemical_formula_weight 396.39 _chemical_absolute_configuration rm 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 P2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 9.7860(10) _cell_length_b 10.0112(11) _cell_length_c 10.4204(11) _cell_angle_alpha 90.00 _cell_angle_beta 107.503(2) _cell_angle_gamma 90.00 _cell_volume 973.62(18) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 7532 _cell_measurement_theta_min 2.50 _cell_measurement_theta_max 28.27 _exptl_crystal_description cubes _exptl_crystal_colour colorless _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.34 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas not_measured _exptl_crystal_density_diffrn 1.352 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 420 _exptl_absorpt_coefficient_mu 0.107 _exptl_absorpt_correction_type 'multi-scan' _exptl_absorpt_correction_T_min 0.9534 _exptl_absorpt_correction_T_max 0.9686 _exptl_absorpt_process_details 'SADABS, Sheldrick, 1997' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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_reflns_number 9293 _diffrn_reflns_av_R_equivalents 0.0183 _diffrn_reflns_av_sigmaI/netI 0.0228 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.05 _diffrn_reflns_theta_max 28.28 _reflns_number_total 4516 _reflns_number_gt 4427 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _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^)+(0.0748P)^2^+0.1614P] 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 constr _refine_ls_extinction_method none _refine_ls_number_reflns 4516 _refine_ls_number_parameters 253 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0374 _refine_ls_R_factor_gt 0.0368 _refine_ls_wR_factor_ref 0.1040 _refine_ls_wR_factor_gt 0.1030 _refine_ls_goodness_of_fit_ref 1.041 _refine_ls_restrained_S_all 1.041 _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 0.98255(11) 0.62260(10) 0.01892(10) 0.0189(2) Uani 1 1 d . . . H1A H 1.0140 0.5785 -0.0347 0.028 Uiso 1 1 calc R . . O2 O 0.78350(11) 0.54109(11) 0.18126(11) 0.0226(2) Uani 1 1 d . . . H2A H 0.6954 0.5449 0.1403 0.034 Uiso 1 1 calc R . . O3 O 1.03449(11) 0.73527(11) 0.51643(10) 0.0220(2) Uani 1 1 d . . . O4 O 1.21000(14) 0.69432(14) 0.72151(12) 0.0320(3) Uani 1 1 d . . . O5 O 1.40824(13) 1.11726(13) 0.62507(11) 0.0287(2) Uani 1 1 d . . . O6 O 1.36256(14) 1.21205(13) 0.42146(12) 0.0318(3) Uani 1 1 d . . . O7 O 1.48953(11) 0.50579(12) 0.04467(11) 0.0253(2) Uani 1 1 d . . . O8 O 1.35565(12) 0.36020(11) 0.12127(12) 0.0279(3) Uani 1 1 d . . . N1 N 1.09886(12) 0.87024(12) 0.09339(11) 0.0179(2) Uani 1 1 d . . . H1B H 1.0154 0.8898 0.0353 0.021 Uiso 1 1 calc R . . N2 N 1.27344(13) 0.56767(12) 0.07128(12) 0.0186(2) Uani 1 1 d . . . C1 C 1.07681(13) 0.79168(13) 0.31253(13) 0.0161(2) Uani 1 1 d . . . C2 C 1.10122(14) 0.81998(15) 0.45056(13) 0.0183(3) Uani 1 1 d . . . C3 C 1.18826(14) 0.92559(15) 0.51366(13) 0.0186(3) Uani 1 1 d . . . H3A H 1.2092 0.9396 0.6078 0.022 Uiso 1 1 calc R . . C4 C 1.24414(14) 1.01051(14) 0.43549(14) 0.0184(3) Uani 1 1 d . . . C5 C 1.21104(14) 0.99280(14) 0.29713(14) 0.0177(3) Uani 1 1 d . . . H5A H 1.2447 1.0547 0.2445 0.021 Uiso 1 1 calc R . . C6 C 1.12776(14) 0.88312(14) 0.23572(13) 0.0174(3) Uani 1 1 d . . . C7 C 1.22260(15) 0.82082(14) 0.05252(13) 0.0196(3) Uani 1 1 d . . . H7A H 1.2930 0.8941 0.0628 0.023 Uiso 1 1 calc R . . H7B H 1.1889 0.7959 -0.0438 0.023 Uiso 1 1 calc R . . C8 C 1.29714(15) 0.70046(15) 0.13418(13) 0.0182(3) Uani 1 1 d . . . H8A H 1.3970 0.7175 0.1932 0.022 Uiso 1 1 calc R . . C9 C 1.21734(14) 0.59289(13) 0.18346(13) 0.0172(3) Uani 1 1 d . . . H9A H 1.2731 0.5501 0.2701 0.021 Uiso 1 1 calc R . . C10 C 1.05552(14) 0.58376(14) 0.15279(13) 0.0173(3) Uani 1 1 d . . . H10A H 1.0326 0.4873 0.1606 0.021 Uiso 1 1 calc R . . C11 C 1.00277(14) 0.66004(14) 0.25868(13) 0.0164(2) Uani 1 1 d . . . H11A H 1.0239 0.5993 0.3385 0.020 Uiso 1 1 calc R . . C12 C 0.83914(15) 0.67327(14) 0.20988(15) 0.0199(3) Uani 1 1 d . . . H12A H 0.8043 0.7148 0.2804 0.024 Uiso 1 1 calc R . . H12B H 0.8086 0.7294 0.1280 0.024 Uiso 1 1 calc R . . C13 C 1.07294(17) 0.74273(17) 0.65977(14) 0.0253(3) Uani 1 1 d . . . H13A H 1.0675 0.8369 0.6868 0.030 Uiso 1 1 calc R . . H13B H 1.0033 0.6905 0.6912 0.030 Uiso 1 1 calc R . . C14 C 1.2188(2) 0.5526(2) 0.7139(2) 0.0434(5) Uani 1 1 d . . . H14A H 1.3172 0.5238 0.7595 0.065 Uiso 1 1 calc R . . H14B H 1.1918 0.5251 0.6193 0.065 Uiso 1 1 calc R . . H14C H 1.1535 0.5115 0.7576 0.065 Uiso 1 1 calc R . . C15 C 1.34562(15) 1.11703(15) 0.50605(15) 0.0204(3) Uani 1 1 d . . . C16 C 1.4676(2) 1.31340(19) 0.4813(2) 0.0389(4) Uani 1 1 d . . . H16A H 1.4723 1.3783 0.4123 0.058 Uiso 1 1 calc R . . H16B H 1.5616 1.2715 0.5192 0.058 Uiso 1 1 calc R . . H16C H 1.4400 1.3591 0.5529 0.058 Uiso 1 1 calc R . . C17 C 1.38524(15) 0.48028(15) 0.08010(14) 0.0199(3) Uani 1 1 d . . . C18 C 1.4565(2) 0.25648(18) 0.1163(2) 0.0405(4) Uani 1 1 d . . . H18A H 1.4274 0.1724 0.1485 0.061 Uiso 1 1 calc R . . H18B H 1.5522 0.2814 0.1736 0.061 Uiso 1 1 calc R . . H18C H 1.4583 0.2453 0.0234 0.061 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 0.0210(5) 0.0185(5) 0.0150(4) -0.0019(4) 0.0023(3) -0.0005(4) O2 0.0179(4) 0.0220(5) 0.0255(5) -0.0030(4) 0.0031(4) -0.0033(4) O3 0.0236(5) 0.0269(5) 0.0159(5) -0.0022(4) 0.0065(4) -0.0089(4) O4 0.0328(6) 0.0314(6) 0.0257(5) 0.0035(5) -0.0005(5) -0.0102(5) O5 0.0294(6) 0.0325(6) 0.0213(5) -0.0049(5) 0.0033(4) -0.0114(5) O6 0.0383(6) 0.0237(5) 0.0275(6) 0.0000(5) 0.0008(5) -0.0135(5) O7 0.0192(5) 0.0289(6) 0.0280(5) -0.0003(4) 0.0075(4) 0.0000(4) O8 0.0261(5) 0.0199(5) 0.0414(7) 0.0052(5) 0.0157(5) 0.0057(4) N1 0.0193(5) 0.0177(5) 0.0148(5) 0.0012(4) 0.0023(4) 0.0015(4) N2 0.0198(5) 0.0177(5) 0.0190(5) -0.0006(4) 0.0067(4) 0.0008(4) C1 0.0148(6) 0.0148(6) 0.0174(6) -0.0010(5) 0.0029(4) 0.0005(5) C2 0.0168(6) 0.0201(6) 0.0178(6) 0.0011(5) 0.0048(5) 0.0007(5) C3 0.0177(6) 0.0209(6) 0.0166(6) -0.0030(5) 0.0041(4) -0.0010(5) C4 0.0156(6) 0.0175(6) 0.0206(6) -0.0017(5) 0.0031(5) 0.0005(5) C5 0.0170(6) 0.0157(6) 0.0195(6) 0.0008(5) 0.0040(5) -0.0007(5) C6 0.0171(6) 0.0168(6) 0.0163(6) -0.0004(5) 0.0021(4) 0.0021(5) C7 0.0250(7) 0.0183(6) 0.0163(6) 0.0026(5) 0.0076(5) 0.0029(5) C8 0.0187(6) 0.0183(6) 0.0171(6) -0.0003(5) 0.0045(5) 0.0007(5) C9 0.0173(6) 0.0173(6) 0.0168(6) 0.0005(5) 0.0046(5) 0.0016(5) C10 0.0164(6) 0.0171(6) 0.0172(6) -0.0006(5) 0.0032(5) -0.0004(5) C11 0.0161(6) 0.0165(6) 0.0155(6) -0.0005(5) 0.0033(5) -0.0015(5) C12 0.0171(6) 0.0210(7) 0.0209(6) -0.0029(5) 0.0045(5) -0.0007(5) C13 0.0298(7) 0.0316(8) 0.0159(6) -0.0024(6) 0.0087(5) -0.0085(6) C14 0.0448(10) 0.0331(9) 0.0424(10) 0.0039(8) -0.0017(8) -0.0067(8) C15 0.0195(6) 0.0187(6) 0.0222(6) -0.0043(5) 0.0052(5) -0.0011(5) C16 0.0453(10) 0.0290(8) 0.0354(9) 0.0006(7) 0.0014(8) -0.0206(8) C17 0.0194(6) 0.0206(6) 0.0186(6) -0.0007(5) 0.0037(5) 0.0010(5) C18 0.0373(9) 0.0244(8) 0.0663(13) 0.0076(8) 0.0254(9) 0.0126(7) _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 C10 1.4170(15) . ? O2 C12 1.4278(17) . ? O3 C2 1.3734(17) . ? O3 C13 1.4284(16) . ? O4 C13 1.389(2) . ? O4 C14 1.425(2) . ? O5 C15 1.2068(18) . ? O6 C15 1.3406(19) . ? O6 C16 1.4453(19) . ? O7 C17 1.2124(18) . ? O8 C17 1.3370(18) . ? O8 C18 1.4440(19) . ? N1 C6 1.4297(16) . ? N1 C7 1.4841(18) . ? N2 C17 1.3821(18) . ? N2 C9 1.4552(17) . ? N2 C8 1.4695(18) . ? C1 C6 1.4026(19) . ? C1 C2 1.4140(18) . ? C1 C11 1.5271(18) . ? C2 C3 1.3924(19) . ? C3 C4 1.398(2) . ? C4 C5 1.3908(18) . ? C4 C15 1.4916(19) . ? C5 C6 1.4021(19) . ? C7 C8 1.5280(19) . ? C8 C9 1.5081(19) . ? C9 C10 1.5212(18) . ? C10 C11 1.5523(18) . ? C11 C12 1.5332(19) . ? 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 C2 O3 C13 118.36(11) . . ? C13 O4 C14 112.82(14) . . ? C15 O6 C16 115.28(13) . . ? C17 O8 C18 114.76(13) . . ? C6 N1 C7 113.82(11) . . ? C17 N2 C9 122.60(12) . . ? C17 N2 C8 121.83(12) . . ? C9 N2 C8 62.08(9) . . ? C6 C1 C2 118.00(12) . . ? C6 C1 C11 124.35(12) . . ? C2 C1 C11 117.58(11) . . ? O3 C2 C3 123.24(12) . . ? O3 C2 C1 115.11(12) . . ? C3 C2 C1 121.64(12) . . ? C2 C3 C4 118.54(12) . . ? C5 C4 C3 121.11(13) . . ? C5 C4 C15 121.00(12) . . ? C3 C4 C15 117.83(12) . . ? C4 C5 C6 119.68(12) . . ? C1 C6 C5 120.55(12) . . ? C1 C6 N1 122.67(12) . . ? C5 C6 N1 116.78(12) . . ? N1 C7 C8 113.40(11) . . ? N2 C8 C9 58.50(9) . . ? N2 C8 C7 118.70(11) . . ? C9 C8 C7 122.92(12) . . ? N2 C9 C8 59.42(9) . . ? N2 C9 C10 116.18(11) . . ? C8 C9 C10 125.75(11) . . ? O1 C10 C9 112.02(11) . . ? O1 C10 C11 112.82(11) . . ? C9 C10 C11 111.64(11) . . ? C1 C11 C12 112.34(11) . . ? C1 C11 C10 117.60(11) . . ? C12 C11 C10 110.13(11) . . ? O2 C12 C11 106.49(11) . . ? O4 C13 O3 112.34(12) . . ? O5 C15 O6 123.32(14) . . ? O5 C15 C4 124.40(14) . . ? O6 C15 C4 112.26(12) . . ? O7 C17 O8 124.78(14) . . ? O7 C17 N2 124.64(14) . . ? O8 C17 N2 110.30(12) . . ? _diffrn_measured_fraction_theta_max 0.982 _diffrn_reflns_theta_full 28.28 _diffrn_measured_fraction_theta_full 0.982 _refine_diff_density_max 0.544 _refine_diff_density_min -0.440 _refine_diff_density_rms 0.056