# Supplementary Material (ESI) for Perkin Transactions # This journal is © The Royal Society of Chemistry 2000 # CCDC Number: 188/207 data_2 _audit_creation_ 99_06_01 _audit_creation_method SHELXL _chemical_name_systematic ; methyl 6-O-propanoyl-alpha-D-galactopyranoside ; _chemical_formula_moiety 'C10 H18 O7' _chemical_formula_sum 'C10 H18 O7' _chemical_formula_weight 250.24 _chemical_melting_point 170.5 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' '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 5.767(1) _cell_length_b 7.971(1) _cell_length_c 13.462(1) _cell_angle_alpha 90.00 _cell_angle_beta 91.47(1) _cell_angle_gamma 90.00 _cell_volume 618.63(4) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 8192 _cell_measurement_theta_min 1.51 _cell_measurement_theta_max 30.30 _exptl_crystal_description plate _exptl_crystal_colour clear _exptl_crystal_size_max .1 _exptl_crystal_size_mid .5 _exptl_crystal_size_min .5 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.343 _exptl_crystal_density_method ? _exptl_crystal_F_000 268 _exptl_absorpt_coefficient_mu 0.114 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Bruker smart' _diffrn_measurement_method '\w scans' _diffrn_standards_number 50 _diffrn_standards_decay_% 0.0094 _diffrn_reflns_number 4521 _diffrn_reflns_av_R_equivalents 0.0207 _diffrn_reflns_av_sigmaI/netI 0.0417 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.51 _diffrn_reflns_theta_max 30.30 _reflns_number_total 3170 _reflns_number_observed 2851 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'Bruker SAINT' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement on F^2^ for ALL reflections except for 0 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.0664P)^2^+0.0383P] 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 'noref' _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3170 _refine_ls_number_parameters 157 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0481 _refine_ls_R_factor_obs 0.0432 _refine_ls_wR_factor_all 0.1150 _refine_ls_wR_factor_obs 0.1122 _refine_ls_goodness_of_fit_all 1.037 _refine_ls_goodness_of_fit_obs 1.068 _refine_ls_restrained_S_all 1.036 _refine_ls_restrained_S_obs 1.068 _refine_ls_shift/esd_max 0.000 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group C1 C -0.5031(3) 0.0004(2) -0.61775(13) 0.0267(3) Uani 1 d . . H1A H -0.6582(3) 0.0228(2) -0.59281(13) 0.032 Uiso 1 calc R . C2 C -0.3476(2) -0.0572(2) -0.53065(12) 0.0224(3) Uani 1 d . . H2A H -0.4212(2) -0.1551(2) -0.50072(12) 0.027 Uiso 1 calc R . C3 C -0.1122(2) -0.1129(2) -0.56815(11) 0.0231(3) Uani 1 d . . H3A H -0.0345(2) -0.0152(2) -0.59640(11) 0.028 Uiso 1 calc R . C4 C -0.1424(3) -0.2455(2) -0.64931(12) 0.0259(3) Uani 1 d . . H4A H 0.0096(3) -0.2664(2) -0.67780(12) 0.031 Uiso 1 calc R . C5 C -0.3023(3) -0.1734(2) -0.73106(12) 0.0303(3) Uani 1 d . . H5A H -0.2291(3) -0.0744(2) -0.75996(12) 0.036 Uiso 1 calc R . C6 C -0.3526(4) -0.3004(3) -0.8119(2) 0.0447(5) Uani 1 d . . H6A H -0.2103(4) -0.3562(3) -0.8300(2) 0.054 Uiso 1 calc R . H6B H -0.4594(4) -0.3846(3) -0.7883(2) 0.054 Uiso 1 calc R . O1 O -0.4131(2) 0.15089(14) -0.65439(10) 0.0362(3) Uani 1 d . . O2 O -0.3259(2) 0.06866(13) -0.45611(9) 0.0274(2) Uani 1 d . . H2 H -0.2433(34) 0.1630(11) -0.4819(5) 0.041 Uiso 1 calc R . O3 O 0.0302(2) -0.17790(15) -0.48962(9) 0.0312(3) Uani 1 d . . H3 H 0.0758(34) -0.0885(5) -0.4456(10) 0.047 Uiso 1 calc R . O4 O -0.2288(2) -0.40132(13) -0.61269(9) 0.0290(2) Uani 1 d . . H4 H -0.3847(14) -0.3862(7) -0.5910(15) 0.044 Uiso 1 calc R . O5 O -0.5219(2) -0.12642(14) -0.69126(9) 0.0307(3) Uani 1 d . . O7 O -0.7730(4) -0.3686(4) -0.8904(2) 0.1016(9) Uani 1 d . . O6 O -0.4531(3) -0.2157(2) -0.89736(10) 0.0512(4) Uani 1 d . . C7 C -0.5722(5) 0.2340(3) -0.7208(2) 0.0591(6) Uani 1 d . . H7A H -0.5036(5) 0.3361(3) -0.7440(2) 0.089 Uiso 1 calc R . H7B H -0.7120(5) 0.2597(3) -0.6867(2) 0.089 Uiso 1 calc R . H7C H -0.6080(5) 0.1623(3) -0.7764(2) 0.089 Uiso 1 calc R . C8 C -0.6629(4) -0.2622(3) -0.9302(2) 0.0521(5) Uani 1 d . . C9 C -0.7361(6) -0.1605(5) -1.0196(2) 0.0772(9) Uani 1 d . . H9A H -0.7866(6) -0.0507(5) -0.9978(2) 0.093 Uiso 1 calc R . H9B H -0.6033(6) -0.1447(5) -1.0614(2) 0.093 Uiso 1 calc R . C10 C -0.9284(7) -0.2408(6) -1.0799(3) 0.0927(12) Uani 1 d . . H10A H -0.9679(7) -0.1708(6) -1.1358(3) 0.139 Uiso 1 calc R . H10B H -1.0617(7) -0.2546(6) -1.0395(3) 0.139 Uiso 1 calc R . H10C H -0.8784(7) -0.3486(6) -1.1030(3) 0.139 Uiso 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 C1 0.0194(6) 0.0241(7) 0.0364(9) 0.0032(6) -0.0024(6) 0.0004(5) C2 0.0182(6) 0.0196(6) 0.0293(7) -0.0002(5) 0.0008(5) -0.0011(5) C3 0.0171(6) 0.0205(6) 0.0317(8) 0.0006(6) 0.0001(5) -0.0003(5) C4 0.0233(6) 0.0229(7) 0.0315(8) -0.0013(6) 0.0045(5) 0.0010(5) C5 0.0359(8) 0.0255(7) 0.0296(8) 0.0022(6) 0.0001(6) -0.0019(6) C6 0.0589(12) 0.0408(10) 0.0339(10) -0.0074(8) -0.0070(8) 0.0026(9) O1 0.0422(6) 0.0220(5) 0.0439(7) 0.0066(5) -0.0067(5) 0.0003(5) O2 0.0247(5) 0.0234(5) 0.0342(6) -0.0049(5) 0.0008(4) -0.0012(4) O3 0.0269(5) 0.0283(5) 0.0379(6) -0.0043(5) -0.0105(4) 0.0072(4) O4 0.0268(5) 0.0199(5) 0.0403(6) 0.0027(5) -0.0003(4) 0.0000(4) O5 0.0260(5) 0.0300(6) 0.0358(6) 0.0003(5) -0.0062(4) -0.0028(4) O7 0.0729(13) 0.115(2) 0.115(2) 0.053(2) -0.0252(13) -0.0282(14) O6 0.0662(9) 0.0548(9) 0.0321(7) 0.0043(7) -0.0098(6) -0.0140(7) C7 0.086(2) 0.0388(11) 0.0516(13) 0.0129(9) -0.0170(12) 0.0163(11) C8 0.0557(13) 0.0516(13) 0.0485(13) 0.0032(10) -0.0067(10) -0.0016(10) C9 0.094(2) 0.076(2) 0.060(2) 0.012(2) -0.0280(14) -0.005(2) C10 0.095(2) 0.099(3) 0.082(2) 0.010(2) -0.039(2) -0.011(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 C1 O1 1.401(2) . no C1 O5 1.417(2) . no C1 C2 1.529(2) . no C2 O2 1.422(2) . no C2 C3 1.526(2) . no C3 O3 1.420(2) . no C3 C4 1.527(2) . no C4 O4 1.430(2) . no C4 C5 1.529(2) . no C5 O5 1.438(2) . no C5 C6 1.509(3) . no C6 O6 1.443(3) . no O1 C7 1.427(2) . no O7 C8 1.195(3) . no O6 C8 1.330(3) . no C8 C9 1.502(4) . no C9 C10 1.501(4) . no 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 C1 O5 112.78(13) . . no O1 C1 C2 108.18(12) . . no O5 C1 C2 110.74(12) . . no O2 C2 C3 112.07(11) . . no O2 C2 C1 111.61(12) . . no C3 C2 C1 110.05(12) . . no O3 C3 C2 111.22(13) . . no O3 C3 C4 109.47(12) . . no C2 C3 C4 110.61(11) . . no O4 C4 C3 112.88(13) . . no O4 C4 C5 111.44(13) . . no C3 C4 C5 108.07(12) . . no O5 C5 C6 106.76(15) . . no O5 C5 C4 110.51(13) . . no C6 C5 C4 111.59(14) . . no O6 C6 C5 109.1(2) . . no C1 O1 C7 112.3(2) . . no C1 O5 C5 113.18(11) . . no C8 O6 C6 118.6(2) . . no O7 C8 O6 122.5(2) . . no O7 C8 C9 126.9(3) . . no O6 C8 C9 110.5(2) . . no C10 C9 C8 113.1(3) . . no 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 O1 C1 C2 O2 55.8(2) . . . . no O5 C1 C2 O2 179.83(11) . . . . no O1 C1 C2 C3 -69.3(2) . . . . no O5 C1 C2 C3 54.7(2) . . . . no O2 C2 C3 O3 59.2(2) . . . . no C1 C2 C3 O3 -176.00(12) . . . . no O2 C2 C3 C4 -178.95(12) . . . . no C1 C2 C3 C4 -54.1(2) . . . . no O3 C3 C4 O4 54.61(15) . . . . no C2 C3 C4 O4 -68.3(2) . . . . no O3 C3 C4 C5 178.31(12) . . . . no C2 C3 C4 C5 55.42(15) . . . . no O4 C4 C5 O5 66.4(2) . . . . no C3 C4 C5 O5 -58.1(2) . . . . no O4 C4 C5 C6 -52.2(2) . . . . no C3 C4 C5 C6 -176.76(14) . . . . no O5 C5 C6 O6 73.4(2) . . . . yes C4 C5 C6 O6 -165.8(2) . . . . yes O5 C1 O1 C7 70.2(2) . . . . no C2 C1 O1 C7 -167.0(2) . . . . no O1 C1 O5 C5 62.0(2) . . . . no C2 C1 O5 C5 -59.4(2) . . . . no C6 C5 O5 C1 -176.62(13) . . . . no C4 C5 O5 C1 61.8(2) . . . . no C5 C6 O6 C8 -120.9(2) . . . . yes C6 O6 C8 O7 1.7(4) . . . . no C6 O6 C8 C9 -179.6(2) . . . . yes O7 C8 C9 C10 -20.5(5) . . . . no O6 C8 C9 C10 160.9(3) . . . . no _refine_diff_density_max 0.260 _refine_diff_density_min -0.190 _refine_diff_density_rms 0.043 data_4 _audit_creation_ 99_06_01 _audit_creation_method SHELXL _chemical_name_systematic ; methyl 6-O-pentanoyl-alpha-D-galactopyranoside ; _chemical_formula_moiety 'C12 H22 O7' _chemical_formula_sum 'C12 H22 O7' _chemical_formula_weight 278.30 _chemical_melting_point 155.7 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' '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 5.770(1) _cell_length_b 7.973(1) _cell_length_c 15.451(1) _cell_angle_alpha 90.00 _cell_angle_beta 93.69(1) _cell_angle_gamma 90.00 _cell_volume 709.3(1) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 8635 _cell_measurement_theta_min 2.64 _cell_measurement_theta_max 30.44 _exptl_crystal_description plate _exptl_crystal_colour clear _exptl_crystal_size_max .04 _exptl_crystal_size_mid .4 _exptl_crystal_size_min .4 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.303 _exptl_crystal_F_000 300 _exptl_absorpt_coefficient_mu 0.107 _exptl_absorpt_correction_type 'empirical' _exptl_absorpt_correction_T_min 0.35 _exptl_absorpt_correction_T_max 1.00 _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Bruker SMART' _diffrn_measurement_method '\w scans' _diffrn_standards_number 50 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% -0.02 _diffrn_reflns_number 5281 _diffrn_reflns_av_R_equivalents 0.0274 _diffrn_reflns_av_sigmaI/netI 0.0567 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.64 _diffrn_reflns_theta_max 30.44 _reflns_number_total 3321 _reflns_number_observed 2766 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'Bruker SAINT' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement on F^2^ for ALL reflections except for 0 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.0990P)^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 'noref' _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 0.18(110) _refine_ls_number_reflns 3321 _refine_ls_number_parameters 175 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0618 _refine_ls_R_factor_obs 0.0533 _refine_ls_wR_factor_all 0.1503 _refine_ls_wR_factor_obs 0.1438 _refine_ls_goodness_of_fit_all 1.010 _refine_ls_goodness_of_fit_obs 1.063 _refine_ls_restrained_S_all 1.010 _refine_ls_restrained_S_obs 1.062 _refine_ls_shift/esd_max 0.000 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group C1 C -0.5226(3) -0.5807(2) -0.60210(13) 0.0287(4) Uani 1 d . . H1A H -0.3622(3) -0.6027(2) -0.58031(13) 0.034 Uiso 1 calc R . C2 C -0.6588(3) -0.5239(2) -0.52629(12) 0.0247(3) Uani 1 d . . H2A H -0.5789(3) -0.4263(2) -0.49998(12) 0.030 Uiso 1 calc R . C3 C -0.9016(3) -0.4680(2) -0.55912(12) 0.0260(4) Uani 1 d . . H3A H -0.9850(3) -0.5656(2) -0.58391(12) 0.031 Uiso 1 calc R . C4 C -0.8884(3) -0.3356(2) -0.62991(13) 0.0278(4) Uani 1 d . . H5A H -1.0463(3) -0.3145(2) -0.65476(13) 0.033 Uiso 1 calc R . C5 C -0.7468(3) -0.4076(3) -0.70080(13) 0.0321(4) Uani 1 d . . H5B H -0.8261(3) -0.5069(3) -0.72567(13) 0.038 Uiso 1 calc R . C6 C -0.7145(5) -0.2824(3) -0.7715(2) 0.0464(5) Uani 1 d . . H6A H -0.8608(5) -0.2269(3) -0.7871(2) 0.056 Uiso 1 calc R . H6B H -0.6029(5) -0.1979(3) -0.7512(2) 0.056 Uiso 1 calc R . C7 C -0.4732(6) -0.8144(4) -0.6916(2) 0.0590(7) Uani 1 d . . H7A H -0.5458(6) -0.9168(4) -0.7117(2) 0.088 Uiso 1 calc R . H7B H -0.3263(6) -0.8394(4) -0.6616(2) 0.088 Uiso 1 calc R . H7C H -0.4493(6) -0.7429(4) -0.7402(2) 0.088 Uiso 1 calc R . O1 O -0.6191(3) -0.7316(2) -0.63393(11) 0.0377(3) Uani 1 d . . O2 O -0.6655(2) -0.6496(2) -0.46168(10) 0.0296(3) Uani 1 d . . H2 H -0.7683(37) -0.7379(16) -0.4819(7) 0.044 Uiso 1 calc R . O3 O -1.0284(2) -0.4034(2) -0.49074(10) 0.0338(3) Uani 1 d . . H3 H -1.0674(43) -0.4933(6) -0.4530(11) 0.051 Uiso 1 calc R . O4 O -0.7948(2) -0.1813(2) -0.59772(10) 0.0325(3) Uani 1 d . . H4 H -0.6310(9) -0.1938(10) -0.5842(18) 0.049 Uiso 1 calc R . O5 O -0.5190(2) -0.4546(2) -0.66615(10) 0.0333(3) Uani 1 d . . O6 O -0.6328(3) -0.3663(3) -0.84618(11) 0.0531(5) Uani 1 d . . O7 O -0.3155(5) -0.2101(5) -0.8414(2) 0.1166(15) Uani 1 d . . C8 C -0.4336(5) -0.3183(4) -0.8759(2) 0.0584(7) Uani 1 d . . C9 C -0.3802(6) -0.4145(6) -0.9548(2) 0.0782(10) Uani 1 d . . H9A H -0.5206(6) -0.4241(6) -0.9925(2) 0.094 Uiso 1 calc R . H9B H -0.3320(6) -0.5269(6) -0.9378(2) 0.094 Uiso 1 calc R . C10 C -0.1918(6) -0.3348(5) -1.0051(2) 0.0733(9) Uani 1 d . . H10A H -0.2297(6) -0.2177(5) -1.0156(2) 0.088 Uiso 1 calc R . H10B H -0.0456(6) -0.3393(5) -0.9704(2) 0.088 Uiso 1 calc R . C11 C -0.1639(8) -0.4201(7) -1.0896(3) 0.0897(12) Uani 1 d . . H11A H -0.3125(8) -0.4217(7) -1.1228(3) 0.108 Uiso 1 calc R . H11B H -0.1169(8) -0.5355(7) -1.0788(3) 0.108 Uiso 1 calc R . C12 C 0.0144(8) -0.3346(8) -1.1428(3) 0.1009(15) Uani 1 d . . H12A H 0.0261(8) -0.3939(8) -1.1964(3) 0.151 Uiso 1 calc R . H12B H 0.1627(8) -0.3348(8) -1.1109(3) 0.151 Uiso 1 calc R . H12C H -0.0329(8) -0.2211(8) -1.1548(3) 0.151 Uiso 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 C1 0.0209(7) 0.0226(8) 0.0432(10) -0.0004(8) 0.0060(7) -0.0010(6) C2 0.0180(6) 0.0180(7) 0.0379(9) 0.0007(7) 0.0018(6) -0.0010(6) C3 0.0174(6) 0.0197(7) 0.0413(9) -0.0014(7) 0.0050(6) 0.0002(6) C4 0.0228(7) 0.0214(8) 0.0390(9) 0.0005(7) 0.0003(7) -0.0002(7) C5 0.0323(9) 0.0257(9) 0.0382(9) -0.0019(8) 0.0028(7) -0.0018(8) C6 0.0589(13) 0.0385(12) 0.0428(12) 0.0052(10) 0.0119(11) 0.0026(11) C7 0.080(2) 0.0393(14) 0.060(2) -0.0108(11) 0.0206(14) 0.0163(13) O1 0.0409(7) 0.0215(7) 0.0515(8) -0.0065(6) 0.0087(7) 0.0000(6) O2 0.0241(6) 0.0224(6) 0.0423(8) 0.0052(5) 0.0023(5) 0.0009(5) O3 0.0280(6) 0.0266(6) 0.0483(8) 0.0043(6) 0.0133(6) 0.0067(6) O4 0.0271(6) 0.0196(6) 0.0511(8) -0.0030(6) 0.0050(6) -0.0003(5) O5 0.0267(6) 0.0290(7) 0.0454(7) 0.0022(6) 0.0111(6) -0.0024(5) O6 0.0613(10) 0.0559(12) 0.0433(9) -0.0023(8) 0.0127(8) -0.0092(9) O7 0.088(2) 0.146(3) 0.121(2) -0.062(3) 0.044(2) -0.053(2) C8 0.0550(14) 0.067(2) 0.0541(15) -0.0080(14) 0.0117(12) -0.0018(14) C9 0.085(2) 0.090(3) 0.062(2) -0.010(2) 0.023(2) -0.001(2) C10 0.067(2) 0.081(2) 0.074(2) -0.010(2) 0.020(2) -0.004(2) C11 0.103(3) 0.100(3) 0.069(2) -0.005(2) 0.027(2) -0.008(2) C12 0.097(3) 0.121(4) 0.089(3) 0.011(3) 0.038(2) -0.003(3) _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 O1 1.401(2) . no C1 O5 1.411(2) . no C1 C2 1.521(2) . no C2 O2 1.417(2) . no C2 C3 1.525(2) . no C3 O3 1.420(2) . no C3 C4 1.525(3) . no C4 O4 1.421(2) . no C4 C5 1.520(3) . no C5 O5 1.437(2) . no C5 C6 1.500(3) . no C6 O6 1.439(3) . no C7 O1 1.427(3) . no O6 C8 1.321(3) . no O7 C8 1.202(4) . no C8 C9 1.490(4) . no C9 C10 1.516(5) . no C10 C11 1.491(5) . no C11 C12 1.519(5) . no 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 C1 O5 112.9(2) . . no O1 C1 C2 108.19(14) . . no O5 C1 C2 111.11(14) . . no O2 C2 C1 111.79(14) . . no O2 C2 C3 112.03(13) . . no C1 C2 C3 109.87(15) . . no O3 C3 C2 111.39(15) . . no O3 C3 C4 109.54(14) . . no C2 C3 C4 110.71(13) . . no O4 C4 C5 111.69(15) . . no O4 C4 C3 112.6(2) . . no C5 C4 C3 108.01(15) . . no O5 C5 C6 106.9(2) . . no O5 C5 C4 110.6(2) . . no C6 C5 C4 111.8(2) . . no O6 C6 C5 109.7(2) . . no C1 O1 C7 112.3(2) . . no C1 O5 C5 113.10(13) . . no C8 O6 C6 118.8(2) . . no O7 C8 O6 122.3(3) . . no O7 C8 C9 126.2(3) . . no O6 C8 C9 111.4(3) . . no C8 C9 C10 113.4(3) . . no C11 C10 C9 112.3(4) . . no C10 C11 C12 112.6(4) . . no 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 O1 C1 C2 O2 55.2(2) . . . . no O5 C1 C2 O2 179.59(13) . . . . no O1 C1 C2 C3 -69.9(2) . . . . no O5 C1 C2 C3 54.6(2) . . . . no O2 C2 C3 O3 59.1(2) . . . . no C1 C2 C3 O3 -176.01(14) . . . . no O2 C2 C3 C4 -178.76(15) . . . . no C1 C2 C3 C4 -53.9(2) . . . . no O3 C3 C4 O4 54.9(2) . . . . no C2 C3 C4 O4 -68.3(2) . . . . no O3 C3 C4 C5 178.67(14) . . . . no C2 C3 C4 C5 55.4(2) . . . . no O4 C4 C5 O5 66.1(2) . . . . no C3 C4 C5 O5 -58.2(2) . . . . no O4 C4 C5 C6 -52.9(2) . . . . no C3 C4 C5 C6 -177.2(2) . . . . no O5 C5 C6 O6 73.3(2) . . . . yes C4 C5 C6 O6 -165.6(2) . . . . yes O5 C1 O1 C7 70.0(2) . . . . no C2 C1 O1 C7 -166.6(2) . . . . no O1 C1 O5 C5 62.4(2) . . . . no C2 C1 O5 C5 -59.3(2) . . . . no C6 C5 O5 C1 -176.3(2) . . . . no C4 C5 O5 C1 61.8(2) . . . . no C5 C6 O6 C8 -121.8(3) . . . . yes C6 O6 C8 O7 2.0(5) . . . . no C6 O6 C8 C9 -178.1(3) . . . . yes O7 C8 C9 C10 -15.7(6) . . . . no O6 C8 C9 C10 164.4(3) . . . . no C8 C9 C10 C11 -172.3(3) . . . . no C9 C10 C11 C12 176.5(4) . . . . no _refine_diff_density_max 0.318 _refine_diff_density_min -0.269 _refine_diff_density_rms 0.057 #===END data_6 _audit_creation_ 99_06_01 _audit_creation_method SHELXL _chemical_name_systematic ; methyl 6-O-heptanoyl-alpha-D-galactopyranoside ; _chemical_formula_moiety 'C14 H26 O7' _chemical_formula_sum 'C14 H26 O7' _chemical_formula_weight 306.35 _chemical_melting_point 148.9 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' '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 5.775(1) _cell_length_b 7.946(1) _cell_length_c 17.883(1) _cell_angle_alpha 90.00 _cell_angle_beta 97.15(1) _cell_angle_gamma 90.00 _cell_volume 814.26(9) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 8635 _cell_measurement_theta_min 1.15 _cell_measurement_theta_max 28.33 _exptl_crystal_description plate _exptl_crystal_colour clear _exptl_crystal_size_max .3 _exptl_crystal_size_mid .3 _exptl_crystal_size_min .02 _exptl_crystal_density_diffrn 1.249 _exptl_crystal_F_000 332 _exptl_absorpt_coefficient_mu 0.099 _exptl_absorpt_correction_type 'empirical' _exptl_absorpt_correction_T_min 0.65 _exptl_absorpt_correction_T_max 1.00 _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'Siemens P4' _diffrn_measurement_method '\w scans' _diffrn_standards_number 50 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0.01 _diffrn_reflns_number 5483 _diffrn_reflns_av_R_equivalents 0.0192 _diffrn_reflns_av_sigmaI/netI 0.0371 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 1.15 _diffrn_reflns_theta_max 28.33 _reflns_number_total 3442 _reflns_number_observed 2910 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'Bruker SAINT' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement on F^2^ for ALL reflections except for 1 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.0502P)^2^+0.1622P] 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 noref _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 -0.56(109) _refine_ls_number_reflns 3441 _refine_ls_number_parameters 193 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0583 _refine_ls_R_factor_obs 0.0436 _refine_ls_wR_factor_all 0.1247 _refine_ls_wR_factor_obs 0.1025 _refine_ls_goodness_of_fit_all 1.033 _refine_ls_goodness_of_fit_obs 1.036 _refine_ls_restrained_S_all 1.153 _refine_ls_restrained_S_obs 1.035 _refine_ls_shift/esd_max 0.000 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group C1 C 0.5384(3) 0.7924(3) 0.08942(11) 0.0302(4) Uani 1 d . . H1A H 0.3746(3) 0.7705(3) 0.07055(11) 0.036 Uiso 1 calc R . C2 C 0.6627(3) 0.8504(3) 0.02352(10) 0.0261(4) Uani 1 d . . H2B H 0.5790(3) 0.9489(3) 0.00103(10) 0.031 Uiso 1 calc R . C3 C 0.9111(3) 0.9054(2) 0.05197(10) 0.0261(4) Uani 1 d . . H3B H 0.9982(3) 0.8071(2) 0.07335(10) 0.031 Uiso 1 calc R . C4 C 0.9102(3) 1.0383(3) 0.11352(10) 0.0295(4) Uani 1 d . . H4A H 1.0722(3) 1.0591(3) 0.13495(10) 0.035 Uiso 1 calc R . C5 C 0.7806(3) 0.9661(3) 0.17551(10) 0.0325(4) Uani 1 d . . H5A H 0.8641(3) 0.8669(3) 0.19741(10) 0.039 Uiso 1 calc R . C6 C 0.7598(5) 1.0938(3) 0.23659(12) 0.0460(6) Uani 1 d . . H6A H 0.9077(5) 1.1511(3) 0.24929(12) 0.055 Uiso 1 calc R . H6B H 0.6429(5) 1.1771(3) 0.21891(12) 0.055 Uiso 1 calc R . C7 C 0.5039(6) 0.5577(4) 0.1674(2) 0.0615(7) Uani 1 d . . H7A H 0.5798(6) 0.4550(4) 0.1848(2) 0.092 Uiso 1 calc R . H7B H 0.3521(6) 0.5326(4) 0.1414(2) 0.092 Uiso 1 calc R . H7C H 0.4881(6) 0.6295(4) 0.2096(2) 0.092 Uiso 1 calc R . O1 O 0.6404(3) 0.6411(2) 0.11697(8) 0.0386(3) Uani 1 d . . O2 O 0.6577(2) 0.7244(2) -0.03334(7) 0.0311(3) Uani 1 d . . H2 H 0.7534(34) 0.6311(13) -0.0146(5) 0.047 Uiso 1 calc R . O3 O 1.0263(2) 0.9707(2) -0.00785(7) 0.0342(3) Uani 1 d . . H3 H 1.0655(37) 0.8799(4) -0.0394(8) 0.051 Uiso 1 calc R . O4 O 0.8117(2) 1.1940(2) 0.08580(8) 0.0326(3) Uani 1 d . . H4 H 0.6477(8) 1.1795(7) 0.0703(12) 0.049 Uiso 1 calc R . O5 O 0.5464(2) 0.9188(2) 0.14529(7) 0.0339(3) Uani 1 d . . O6 O 0.6939(3) 1.0095(3) 0.30274(8) 0.0548(5) Uani 1 d . . O7 O 0.3655(4) 1.1570(5) 0.2968(2) 0.1131(12) Uani 1 d . . C8 C 0.4975(5) 1.0560(4) 0.32815(14) 0.0595(8) Uani 1 d . . C9 C 0.4678(5) 0.9645(5) 0.39957(15) 0.0750(9) Uani 1 d . . H9A H 0.6142(5) 0.9677(5) 0.43262(15) 0.090 Uiso 1 calc R . H9B H 0.4321(5) 0.8475(5) 0.38773(15) 0.090 Uiso 1 calc R . C10 C 0.2772(6) 1.0368(5) 0.4411(2) 0.0733(9) Uani 1 d . . H10A H 0.2984(6) 1.1576(5) 0.4457(2) 0.088 Uiso 1 calc R . H10B H 0.1271(6) 1.0165(5) 0.4116(2) 0.088 Uiso 1 calc R . C11 C 0.2750(6) 0.9623(5) 0.51873(15) 0.0751(9) Uani 1 d . . H11A H 0.4283(6) 0.9773(5) 0.54697(15) 0.090 Uiso 1 calc R . H11B H 0.2468(6) 0.8423(5) 0.51361(15) 0.090 Uiso 1 calc R . C12 C 0.0946(5) 1.0374(5) 0.5636(2) 0.0736(9) Uani 1 d . . H12A H 0.1183(5) 1.1582(5) 0.5669(2) 0.088 Uiso 1 calc R . H12B H -0.0593(5) 1.0177(5) 0.5366(2) 0.088 Uiso 1 calc R . C13 C 0.1013(7) 0.9683(7) 0.6413(2) 0.0977(14) Uani 1 d . . H13A H 0.2570(7) 0.9838(7) 0.6677(2) 0.117 Uiso 1 calc R . H13B H 0.0711(7) 0.8483(7) 0.6380(2) 0.117 Uiso 1 calc R . C14 C -0.0725(7) 1.0484(6) 0.6872(2) 0.1000(15) Uani 1 d . . H14A H -0.0582(7) 0.9979(6) 0.7363(2) 0.150 Uiso 1 calc R . H14B H -0.2278(7) 1.0312(6) 0.6623(2) 0.150 Uiso 1 calc R . H14C H -0.0417(7) 1.1668(6) 0.6921(2) 0.150 Uiso 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 C1 0.0231(8) 0.0308(11) 0.0381(10) 0.0004(8) 0.0095(7) -0.0008(7) C2 0.0204(7) 0.0251(10) 0.0335(9) -0.0008(7) 0.0060(6) 0.0021(7) C3 0.0190(7) 0.0258(10) 0.0344(9) 0.0028(7) 0.0073(6) 0.0006(7) C4 0.0239(8) 0.0290(11) 0.0355(9) -0.0016(8) 0.0032(7) 0.0005(7) C5 0.0342(9) 0.0315(11) 0.0320(8) 0.0028(8) 0.0047(7) 0.0019(8) C6 0.0597(13) 0.045(2) 0.0356(11) -0.0073(10) 0.0148(10) -0.0057(11) C7 0.087(2) 0.047(2) 0.0546(14) 0.0112(12) 0.0264(13) -0.0157(14) O1 0.0441(7) 0.0291(8) 0.0446(8) 0.0064(7) 0.0136(6) 0.0008(6) O2 0.0274(6) 0.0286(8) 0.0380(7) -0.0042(6) 0.0064(5) 0.0008(6) O3 0.0321(6) 0.0341(8) 0.0396(7) -0.0050(6) 0.0171(5) -0.0084(6) O4 0.0275(6) 0.0278(8) 0.0433(7) 0.0016(6) 0.0075(5) 0.0002(5) O5 0.0298(6) 0.0364(9) 0.0379(7) -0.0018(6) 0.0135(5) 0.0020(6) O6 0.0652(10) 0.0659(14) 0.0353(8) 0.0020(8) 0.0147(7) 0.0089(9) O7 0.087(2) 0.164(3) 0.097(2) 0.059(2) 0.0439(14) 0.053(2) C8 0.0543(14) 0.082(2) 0.0437(13) 0.0046(14) 0.0126(11) 0.0026(14) C9 0.084(2) 0.094(3) 0.0508(14) 0.012(2) 0.0246(14) 0.005(2) C10 0.073(2) 0.098(3) 0.0535(15) 0.007(2) 0.0244(13) 0.001(2) C11 0.082(2) 0.097(3) 0.0498(14) 0.006(2) 0.0213(13) -0.001(2) C12 0.073(2) 0.093(3) 0.059(2) 0.004(2) 0.0224(14) -0.004(2) C13 0.101(3) 0.139(4) 0.058(2) 0.009(2) 0.030(2) 0.018(3) C14 0.101(3) 0.130(4) 0.076(2) -0.005(2) 0.039(2) 0.005(3) _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 O1 1.401(2) . no C1 O5 1.414(2) . no C1 C2 1.525(2) . no C2 O2 1.425(2) . no C2 C3 1.525(2) . no C3 O3 1.426(2) . no C3 C4 1.526(3) . no C4 O4 1.425(2) . no C4 C5 1.525(2) . no C5 O5 1.443(2) . no C5 C6 1.506(3) . no C6 O6 1.451(3) . no C7 O1 1.432(3) . no O6 C8 1.326(3) . no O7 C8 1.198(4) . no C8 C9 1.498(4) . no C9 C10 1.515(4) . no C10 C11 1.511(4) . no C11 C12 1.514(4) . no C12 C13 1.491(4) . no C13 C14 1.513(5) . no 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 C1 O5 112.7(2) . . no O1 C1 C2 108.27(15) . . no O5 C1 C2 110.7(2) . . no O2 C2 C3 111.98(13) . . no O2 C2 C1 111.7(2) . . no C3 C2 C1 110.01(14) . . no O3 C3 C2 111.18(14) . . no O3 C3 C4 109.4(2) . . no C2 C3 C4 110.58(13) . . no O4 C4 C5 111.63(15) . . no O4 C4 C3 112.79(15) . . no C5 C4 C3 108.1(2) . . no O5 C5 C6 106.9(2) . . no O5 C5 C4 110.35(14) . . no C6 C5 C4 111.4(2) . . no O6 C6 C5 109.5(2) . . no C1 O1 C7 112.2(2) . . no C1 O5 C5 113.37(13) . . no C8 O6 C6 118.2(2) . . no O7 C8 O6 123.2(3) . . no O7 C8 C9 126.2(3) . . no O6 C8 C9 110.5(3) . . no C8 C9 C10 113.7(3) . . no C11 C10 C9 113.0(3) . . no C10 C11 C12 114.7(3) . . no C13 C12 C11 114.2(3) . . no C12 C13 C14 114.1(4) . . no 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 O1 C1 C2 O2 55.7(2) . . . . no O5 C1 C2 O2 179.73(13) . . . . no O1 C1 C2 C3 -69.3(2) . . . . no O5 C1 C2 C3 54.7(2) . . . . no O2 C2 C3 O3 59.0(2) . . . . no C1 C2 C3 O3 -176.2(2) . . . . no O2 C2 C3 C4 -179.2(2) . . . . no C1 C2 C3 C4 -54.4(2) . . . . no O3 C3 C4 O4 54.7(2) . . . . no C2 C3 C4 O4 -68.1(2) . . . . no O3 C3 C4 C5 178.58(14) . . . . no C2 C3 C4 C5 55.8(2) . . . . no O4 C4 C5 O5 66.5(2) . . . . no C3 C4 C5 O5 -58.1(2) . . . . no O4 C4 C5 C6 -52.1(2) . . . . no C3 C4 C5 C6 -176.7(2) . . . . no O5 C5 C6 O6 74.5(2) . . . . yes C4 C5 C6 O6 -164.8(2) . . . . yes O5 C1 O1 C7 70.2(2) . . . . no C2 C1 O1 C7 -167.0(2) . . . . no O1 C1 O5 C5 62.2(2) . . . . no C2 C1 O5 C5 -59.2(2) . . . . no C6 C5 O5 C1 -177.0(2) . . . . no C4 C5 O5 C1 61.6(2) . . . . no C5 C6 O6 C8 -121.0(3) . . . . yes C6 O6 C8 O7 4.4(5) . . . . no C6 O6 C8 C9 -175.9(2) . . . . yes O7 C8 C9 C10 -12.8(5) . . . . no O6 C8 C9 C10 167.5(3) . . . . no C8 C9 C10 C11 -170.6(3) . . . . no C9 C10 C11 C12 177.1(3) . . . . no C10 C11 C12 C13 -177.4(3) . . . . no C11 C12 C13 C14 177.7(3) . . . . no _refine_diff_density_max 0.239 _refine_diff_density_min -0.199 _refine_diff_density_rms 0.037 #===END data_8 _audit_creation_ 99_06_01 _audit_creation_method SHELXL _chemical_name_systematic ; methyl 6-O-nonanoyl-alpha-D-galactopyranoside ; _chemical_formula_moiety 'C16 H30 O7' _chemical_formula_sum 'C16 H30 O7' _chemical_formula_weight 334.40 _chemical_melting_point 146.6 _chemical_compound_source ? 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' '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 5.768(1) _cell_length_b 7.903(1) _cell_length_c 20.114(1) _cell_angle_alpha 90.00 _cell_angle_beta 96.63(1) _cell_angle_gamma 90.00 _cell_volume 910.6(1) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 8634 _cell_measurement_theta_min 1.02 _cell_measurement_theta_max 28.37 _exptl_crystal_description plate _exptl_crystal_colour clear _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.220 _exptl_crystal_density_method ? _exptl_crystal_F_000 364 _exptl_absorpt_coefficient_mu 0.094 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.65 _exptl_absorpt_correction_T_max 1.00 _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus rotatin anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'SMART 1K' _diffrn_measurement_method '\w scans' _diffrn_standards_number 50 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% -0.7 _diffrn_reflns_number 5443 _diffrn_reflns_av_R_equivalents 0.0243 _diffrn_reflns_av_sigmaI/netI 0.0503 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 1.02 _diffrn_reflns_theta_max 28.37 _reflns_number_total 3714 _reflns_number_observed 3026 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'Bruker SAINT' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement on F^2^ for ALL reflections except for 1 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.0424P)^2^+0.1824P] 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 noref _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0287(34) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.51(125) _refine_ls_number_reflns 3713 _refine_ls_number_parameters 212 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0701 _refine_ls_R_factor_obs 0.0515 _refine_ls_wR_factor_all 0.1337 _refine_ls_wR_factor_obs 0.1078 _refine_ls_goodness_of_fit_all 1.060 _refine_ls_goodness_of_fit_obs 1.085 _refine_ls_restrained_S_all 1.209 _refine_ls_restrained_S_obs 1.085 _refine_ls_shift/esd_max 0.000 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group C1 C 0.5286(4) 0.0943(3) 0.57939(12) 0.0315(5) Uani 1 d . . H1A H 0.6787(4) 0.1160(3) 0.56258(12) 0.038 Uiso 1 calc R . C2 C 0.3551(4) 0.0361(3) 0.52131(11) 0.0277(5) Uani 1 d . . H2B H 0.4217(4) -0.0634(3) 0.50144(11) 0.033 Uiso 1 calc R . C3 C 0.1280(3) -0.0181(3) 0.54632(11) 0.0281(5) Uani 1 d . . H3B H 0.0568(3) 0.0810(3) 0.56513(11) 0.034 Uiso 1 calc R . C4 C 0.1736(4) -0.1518(3) 0.60124(11) 0.0307(5) Uani 1 d . . H4A H 0.0272(4) -0.1723(3) 0.62026(11) 0.037 Uiso 1 calc R . C5 C 0.3498(4) -0.0785(3) 0.65611(11) 0.0331(5) Uani 1 d . . H5A H 0.2828(4) 0.0218(3) 0.67530(11) 0.040 Uiso 1 calc R . C6 C 0.4149(5) -0.2061(4) 0.71058(13) 0.0470(7) Uani 1 d . . H6A H 0.2759(5) -0.2639(4) 0.72153(13) 0.056 Uiso 1 calc R . H6B H 0.5195(5) -0.2899(4) 0.69521(13) 0.056 Uiso 1 calc R . C7 C 0.6194(6) 0.3304(4) 0.6487(2) 0.0613(9) Uani 1 d . . H7A H 0.5562(6) 0.4337(4) 0.6641(2) 0.092 Uiso 1 calc R . H7B H 0.7528(6) 0.3555(4) 0.6259(2) 0.092 Uiso 1 calc R . H7C H 0.6656(6) 0.2581(4) 0.6862(2) 0.092 Uiso 1 calc R . O1 O 0.4466(3) 0.2470(2) 0.60380(9) 0.0401(4) Uani 1 d . . O2 O 0.3191(3) 0.1626(2) 0.47062(8) 0.0320(4) Uani 1 d . . H2 H 0.2339(41) 0.2555(15) 0.4867(5) 0.048 Uiso 1 calc R . O3 O -0.0321(3) -0.0843(2) 0.49334(8) 0.0352(4) Uani 1 d . . H3 H -0.0914(36) 0.0063(5) 0.4644(8) 0.053 Uiso 1 calc R . O4 O 0.2519(3) -0.3084(2) 0.57684(8) 0.0336(4) Uani 1 d . . H4 H 0.4049(19) -0.2939(8) 0.5633(12) 0.050 Uiso 1 calc R . O5 O 0.5615(3) -0.0321(2) 0.62933(8) 0.0347(4) Uani 1 d . . O6 O 0.5278(3) -0.1217(3) 0.76939(8) 0.0538(5) Uani 1 d . . O7 O 0.8547(5) -0.2670(5) 0.76473(15) 0.1105(12) Uani 1 d . . C8 C 0.7429(6) -0.1671(5) 0.79223(15) 0.0595(8) Uani 1 d . . C9 C 0.8244(6) -0.0759(5) 0.85618(15) 0.0724(10) Uani 1 d . . H9A H 0.7025(6) -0.0819(5) 0.88551(15) 0.087 Uiso 1 calc R . H9B H 0.8476(6) 0.0424(5) 0.84604(15) 0.087 Uiso 1 calc R . C10 C 1.0472(6) -0.1446(5) 0.8930(2) 0.0744(10) Uani 1 d . . H10A H 1.1753(6) -0.1207(5) 0.8672(2) 0.089 Uiso 1 calc R . H10B H 1.0340(6) -0.2666(5) 0.8967(2) 0.089 Uiso 1 calc R . C11 C 1.1028(6) -0.0704(5) 0.9624(2) 0.0729(10) Uani 1 d . . H11A H 1.1205(6) 0.0511(5) 0.9584(2) 0.087 Uiso 1 calc R . H11B H 0.9716(6) -0.0907(5) 0.9875(2) 0.087 Uiso 1 calc R . C12 C 1.3208(6) -0.1413(6) 1.0014(2) 0.0806(11) Uani 1 d . . H12A H 1.3076(6) -0.2636(6) 1.0025(2) 0.097 Uiso 1 calc R . H12B H 1.4533(6) -0.1140(6) 0.9777(2) 0.097 Uiso 1 calc R . C13 C 1.3694(6) -0.0776(6) 1.07212(15) 0.0785(11) Uani 1 d . . H13A H 1.2359(6) -0.1034(6) 1.09558(15) 0.094 Uiso 1 calc R . H13B H 1.3847(6) 0.0446(6) 1.07095(15) 0.094 Uiso 1 calc R . C14 C 1.5867(6) -0.1504(5) 1.1118(2) 0.0740(10) Uani 1 d . . H14A H 1.5728(6) -0.2727(5) 1.1124(2) 0.089 Uiso 1 calc R . H14B H 1.7208(6) -0.1227(5) 1.0888(2) 0.089 Uiso 1 calc R . C15 C 1.6302(8) -0.0887(7) 1.1817(2) 0.1013(15) Uani 1 d . . H15A H 1.4937(8) -0.1130(7) 1.2041(2) 0.122 Uiso 1 calc R . H15B H 1.6489(8) 0.0332(7) 1.1809(2) 0.122 Uiso 1 calc R . C16 C 1.8412(7) -0.1644(7) 1.2223(2) 0.101(2) Uani 1 d . . H16A H 1.8565(7) -0.1179(7) 1.2667(2) 0.151 Uiso 1 calc R . H16B H 1.9784(7) -0.1385(7) 1.2014(2) 0.151 Uiso 1 calc R . H16C H 1.8229(7) -0.2849(7) 1.2246(2) 0.151 Uiso 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 C1 0.0233(11) 0.0285(13) 0.0423(14) -0.0016(11) 0.0024(9) -0.0012(9) C2 0.0240(10) 0.0242(11) 0.0348(11) -0.0005(9) 0.0032(8) 0.0038(8) C3 0.0226(10) 0.0247(11) 0.0364(12) -0.0023(9) 0.0008(9) -0.0009(9) C4 0.0266(11) 0.0316(13) 0.0351(12) -0.0020(10) 0.0082(9) 0.0007(9) C5 0.0358(12) 0.0306(12) 0.0327(11) -0.0005(10) 0.0032(9) 0.0014(10) C6 0.059(2) 0.043(2) 0.0378(14) 0.0024(11) -0.0012(12) -0.0035(13) C7 0.081(2) 0.042(2) 0.056(2) -0.0096(14) -0.013(2) -0.018(2) O1 0.0444(10) 0.0271(9) 0.0472(10) -0.0073(8) -0.0013(8) -0.0011(7) O2 0.0293(8) 0.0274(9) 0.0395(9) 0.0050(7) 0.0049(6) 0.0016(7) O3 0.0288(8) 0.0316(9) 0.0428(9) 0.0040(7) -0.0062(6) -0.0063(7) O4 0.0304(8) 0.0262(9) 0.0441(9) -0.0008(7) 0.0033(7) -0.0003(7) O5 0.0290(8) 0.0339(9) 0.0397(9) 0.0011(7) -0.0020(7) 0.0021(7) O6 0.0608(12) 0.0609(14) 0.0373(9) -0.0019(9) -0.0047(8) 0.0081(10) O7 0.074(2) 0.155(3) 0.096(2) -0.053(2) -0.0197(15) 0.036(2) C8 0.054(2) 0.073(2) 0.051(2) -0.005(2) 0.0044(14) 0.002(2) C9 0.074(2) 0.086(3) 0.054(2) -0.012(2) -0.009(2) 0.004(2) C10 0.068(2) 0.097(3) 0.054(2) -0.009(2) -0.011(2) 0.001(2) C11 0.074(2) 0.087(3) 0.054(2) -0.003(2) -0.007(2) -0.008(2) C12 0.071(2) 0.111(3) 0.056(2) -0.009(2) -0.009(2) -0.007(2) C13 0.079(2) 0.104(3) 0.050(2) -0.005(2) -0.006(2) -0.002(2) C14 0.069(2) 0.092(3) 0.058(2) -0.007(2) -0.005(2) -0.005(2) C15 0.100(3) 0.138(4) 0.061(2) -0.012(3) -0.015(2) 0.024(3) C16 0.088(3) 0.133(4) 0.075(3) 0.003(3) -0.019(2) 0.004(3) _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 O1 1.405(3) . no C1 O5 1.414(3) . no C1 C2 1.519(3) . no C2 O2 1.426(3) . no C2 C3 1.519(3) . no C3 O3 1.426(3) . no C3 C4 1.529(3) . no C4 O4 1.424(3) . no C4 C5 1.525(3) . no C5 O5 1.438(3) . no C5 C6 1.505(3) . no C6 O6 1.446(3) . no C7 O1 1.426(3) . no O6 C8 1.322(3) . no O7 C8 1.195(4) . no C8 C9 1.502(4) . no C9 C10 1.508(4) . no C10 C11 1.514(4) . no C11 C12 1.511(5) . no C12 C13 1.504(4) . no C13 C14 1.519(5) . no C14 C15 1.483(5) . no C15 C16 1.508(5) . no 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 C1 O5 112.4(2) . . no O1 C1 C2 108.1(2) . . no O5 C1 C2 110.8(2) . . no O2 C2 C3 112.0(2) . . no O2 C2 C1 111.5(2) . . no C3 C2 C1 110.3(2) . . no O3 C3 C2 111.4(2) . . no O3 C3 C4 109.2(2) . . no C2 C3 C4 110.5(2) . . no O4 C4 C5 111.6(2) . . no O4 C4 C3 112.7(2) . . no C5 C4 C3 107.8(2) . . no O5 C5 C6 107.0(2) . . no O5 C5 C4 110.4(2) . . no C6 C5 C4 111.2(2) . . no O6 C6 C5 109.7(2) . . no C1 O1 C7 112.3(2) . . no C1 O5 C5 113.4(2) . . no C8 O6 C6 118.3(2) . . no O7 C8 O6 123.6(3) . . no O7 C8 C9 125.5(3) . . no O6 C8 C9 110.8(3) . . no C8 C9 C10 114.4(3) . . no C9 C10 C11 113.0(3) . . no C12 C11 C10 114.2(3) . . no C13 C12 C11 114.8(3) . . no C12 C13 C14 115.0(3) . . no C15 C14 C13 114.4(3) . . no C14 C15 C16 114.9(4) . . no 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 O1 C1 C2 O2 56.1(2) . . . . no O5 C1 C2 O2 179.7(2) . . . . no O1 C1 C2 C3 -69.0(2) . . . . no O5 C1 C2 C3 54.6(2) . . . . no O2 C2 C3 O3 59.2(2) . . . . no C1 C2 C3 O3 -176.0(2) . . . . no O2 C2 C3 C4 -179.2(2) . . . . no C1 C2 C3 C4 -54.4(2) . . . . no O3 C3 C4 O4 55.0(2) . . . . no C2 C3 C4 O4 -67.9(2) . . . . no O3 C3 C4 C5 178.6(2) . . . . no C2 C3 C4 C5 55.7(2) . . . . no O4 C4 C5 O5 66.1(2) . . . . no C3 C4 C5 O5 -58.2(2) . . . . no O4 C4 C5 C6 -52.5(3) . . . . no C3 C4 C5 C6 -176.8(2) . . . . no O5 C5 C6 O6 75.1(3) . . . . yes C4 C5 C6 O6 -164.2(2) . . . . yes O5 C1 O1 C7 69.9(3) . . . . no C2 C1 O1 C7 -167.5(2) . . . . no O1 C1 O5 C5 62.1(2) . . . . no C2 C1 O5 C5 -59.0(2) . . . . no C6 C5 O5 C1 -177.1(2) . . . . no C4 C5 O5 C1 61.7(2) . . . . no C5 C6 O6 C8 -120.5(3) . . . . yes C6 O6 C8 O7 4.7(5) . . . . no C6 O6 C8 C9 -175.7(3) . . . . yes O7 C8 C9 C10 -12.0(6) . . . . no O6 C8 C9 C10 168.4(3) . . . . no C8 C9 C10 C11 -170.3(3) . . . . no C9 C10 C11 C12 178.0(3) . . . . no C10 C11 C12 C13 -176.0(3) . . . . no C11 C12 C13 C14 179.2(3) . . . . no C12 C13 C14 C15 -179.0(4) . . . . no C13 C14 C15 C16 178.1(4) . . . . no _refine_diff_density_max 0.206 _refine_diff_density_min -0.194 _refine_diff_density_rms 0.038 #===END data_10 _audit_creation_ 99_06_01 _audit_creation_method SHELXL _chemical_name_systematic ; methyl 6-O-undecanoyl-alpha-D-galactopyranoside ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C18 H34 O7' _chemical_formula_weight 362.46 _chemical_melting_point 145.1 _chemical_compound_source ? 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' '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 5.778(1) _cell_length_b 7.903(1) _cell_length_c 22.326(1) _cell_angle_alpha 90.00 _cell_angle_beta 92.83(1) _cell_angle_gamma 90.00 _cell_volume 1018.29(3) _cell_formula_units_Z 3 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 8536 _cell_measurement_theta_min 0.91 _cell_measurement_theta_max 26.39 _exptl_crystal_description plate _exptl_crystal_colour clear _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.182 _exptl_crystal_density_method ? _exptl_crystal_F_000 396 _exptl_absorpt_coefficient_mu 0.090 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.625 _exptl_absorpt_correction_T_max 1.000 _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Bruker smart' _diffrn_measurement_method '\w scans' _diffrn_standards_number 50 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% -0.2 _diffrn_reflns_number 5603 _diffrn_reflns_av_R_equivalents 0.0414 _diffrn_reflns_av_sigmaI/netI 0.0757 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 0.91 _diffrn_reflns_theta_max 26.34 _reflns_number_total 3614 _reflns_number_observed 2715 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'Bruker SAINT' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement on F^2^ for ALL reflections except for 1 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.0448P)^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 noref _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0279(36) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -1.66(130) _refine_ls_number_reflns 3613 _refine_ls_number_parameters 230 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0783 _refine_ls_R_factor_obs 0.0530 _refine_ls_wR_factor_all 0.1398 _refine_ls_wR_factor_obs 0.1092 _refine_ls_goodness_of_fit_all 1.017 _refine_ls_goodness_of_fit_obs 1.062 _refine_ls_restrained_S_all 1.168 _refine_ls_restrained_S_obs 1.062 _refine_ls_shift/esd_max 0.000 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group C1 C 1.0100(4) 0.0681(3) 0.57178(12) 0.0306(6) Uani 1 d . . H1A H 1.1641(4) 0.0896(3) 0.55692(12) 0.037 Uiso 1 calc R . C2 C 0.8517(4) 0.0089(3) 0.51922(11) 0.0282(6) Uani 1 d . . H2B H 0.9230(4) -0.0908(3) 0.50165(11) 0.034 Uiso 1 calc R . C3 C 0.6175(4) -0.0445(3) 0.54167(11) 0.0280(6) Uani 1 d . . H3B H 0.5425(4) 0.0549(3) 0.55837(11) 0.034 Uiso 1 calc R . C4 C 0.6502(4) -0.1785(3) 0.59127(11) 0.0306(6) Uani 1 d . . H4B H 0.4994(4) -0.1986(3) 0.60822(11) 0.037 Uiso 1 calc R . C5 C 0.8129(4) -0.1051(4) 0.64069(11) 0.0342(6) Uani 1 d . . H5A H 0.7413(4) -0.0048(4) 0.65772(11) 0.041 Uiso 1 calc R . C6 C 0.8650(6) -0.2320(4) 0.68971(13) 0.0479(8) Uani 1 d . . H6A H 0.7237(6) -0.2902(4) 0.69932(13) 0.058 Uiso 1 calc R . H6B H 0.9738(6) -0.3155(4) 0.67617(13) 0.058 Uiso 1 calc R . C7 C 1.0862(6) 0.3062(4) 0.63366(15) 0.0620(10) Uani 1 d . . H7A H 1.0193(6) 0.4098(4) 0.64710(15) 0.093 Uiso 1 calc R . H7B H 1.2248(6) 0.3308(4) 0.61331(15) 0.093 Uiso 1 calc R . H7C H 1.1232(6) 0.2347(4) 0.66756(15) 0.093 Uiso 1 calc R . O1 O 0.9230(3) 0.2211(2) 0.59320(8) 0.0393(5) Uani 1 d . . O2 O 0.8264(3) 0.1356(2) 0.47347(8) 0.0320(4) Uani 1 d . . H2 H 0.7444(42) 0.2309(14) 0.4886(4) 0.048 Uiso 1 calc R . O3 O 0.4699(3) -0.1112(2) 0.49408(7) 0.0361(5) Uani 1 d . . H3 H 0.4244(40) -0.0218(7) 0.4669(7) 0.054 Uiso 1 calc R . O4 O 0.7332(3) -0.3357(2) 0.56961(8) 0.0336(4) Uani 1 d . . H4 H 0.8874(18) -0.3212(8) 0.5563(11) 0.050 Uiso 1 calc R . O5 O 1.0313(3) -0.0583(2) 0.61651(7) 0.0360(5) Uani 1 d . . O6 O 0.9627(4) -0.1472(3) 0.74270(8) 0.0539(6) Uani 1 d . . O7 O 1.2916(5) -0.2930(5) 0.73894(13) 0.1093(12) Uani 1 d . . C8 C 1.1741(6) -0.1919(5) 0.76362(14) 0.0576(9) Uani 1 d . . C9 C 1.2371(6) -0.1025(6) 0.82112(14) 0.0725(11) Uani 1 d . . H9A H 1.1083(6) -0.1115(6) 0.84721(14) 0.087 Uiso 1 calc R . H9B H 1.2594(6) 0.0166(6) 0.81260(14) 0.087 Uiso 1 calc R . C10 C 1.4533(6) -0.1693(6) 0.85428(14) 0.0740(11) Uani 1 d . . H10A H 1.5870(6) -0.1432(6) 0.83133(14) 0.089 Uiso 1 calc R . H10B H 1.4424(6) -0.2914(6) 0.85746(14) 0.089 Uiso 1 calc R . C11 C 1.4890(6) -0.0941(6) 0.91695(14) 0.0730(11) Uani 1 d . . H11A H 1.5028(6) 0.0278(6) 0.91348(14) 0.088 Uiso 1 calc R . H11B H 1.3529(6) -0.1175(6) 0.93932(14) 0.088 Uiso 1 calc R . C12 C 1.7015(7) -0.1614(6) 0.9521(2) 0.0810(12) Uani 1 d . . H12A H 1.6928(7) -0.2840(6) 0.9531(2) 0.097 Uiso 1 calc R . H12B H 1.8383(7) -0.1311(6) 0.9311(2) 0.097 Uiso 1 calc R . C13 C 1.7300(6) -0.0968(7) 1.01597(14) 0.0758(11) Uani 1 d . . H13A H 1.7386(6) 0.0257(7) 1.01505(14) 0.091 Uiso 1 calc R . H13B H 1.5932(6) -0.1273(7) 1.03708(14) 0.091 Uiso 1 calc R . C14 C 1.9415(6) -0.1640(7) 1.05081(14) 0.0796(12) Uani 1 d . . H14A H 1.9348(6) -0.2866(7) 1.05066(14) 0.096 Uiso 1 calc R . H14B H 2.0782(6) -0.1309(7) 1.03018(14) 0.096 Uiso 1 calc R . C15 C 1.9686(6) -0.1044(7) 1.11493(14) 0.0799(12) Uani 1 d . . H15A H 1.8306(6) -0.1357(7) 1.13538(14) 0.096 Uiso 1 calc R . H15B H 1.9781(6) 0.0182(7) 1.11506(14) 0.096 Uiso 1 calc R . C16 C 2.1790(7) -0.1744(6) 1.15025(15) 0.0733(11) Uani 1 d . . H16A H 2.1704(7) -0.2969(6) 1.14990(15) 0.088 Uiso 1 calc R . H16B H 2.3172(7) -0.1421(6) 1.13008(15) 0.088 Uiso 1 calc R . C17 C 2.2032(8) -0.1160(8) 1.2137(2) 0.099(2) Uani 1 d . . H17A H 2.0620(8) -0.1439(8) 1.2333(2) 0.119 Uiso 1 calc R . H17B H 2.2181(8) 0.0063(8) 1.2139(2) 0.119 Uiso 1 calc R . C18 C 2.4059(7) -0.1902(7) 1.2499(2) 0.099(2) Uani 1 d . . H18A H 2.4083(7) -0.1460(7) 1.2900(2) 0.149 Uiso 1 calc R . H18B H 2.5474(7) -0.1606(7) 1.2316(2) 0.149 Uiso 1 calc R . H18C H 2.3910(7) -0.3111(7) 1.2511(2) 0.149 Uiso 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 C1 0.0171(12) 0.035(2) 0.039(2) 0.0000(13) 0.0018(11) -0.0013(10) C2 0.0203(12) 0.0294(14) 0.0348(13) -0.0006(11) 0.0014(10) 0.0012(10) C3 0.0194(12) 0.0288(13) 0.0357(13) -0.0037(12) 0.0004(10) -0.0018(10) C4 0.0232(13) 0.035(2) 0.0347(13) -0.0018(13) 0.0063(11) 0.0003(11) C5 0.0308(14) 0.0348(15) 0.0372(13) -0.0013(13) 0.0036(11) -0.0005(11) C6 0.054(2) 0.050(2) 0.039(2) 0.0036(14) -0.0026(14) -0.0045(14) C7 0.084(3) 0.048(2) 0.052(2) -0.012(2) -0.012(2) -0.020(2) O1 0.0391(11) 0.0325(11) 0.0455(11) -0.0082(9) -0.0040(9) -0.0012(8) O2 0.0262(9) 0.0331(10) 0.0369(10) 0.0049(9) 0.0030(7) 0.0000(8) O3 0.0266(9) 0.0397(11) 0.0411(10) 0.0043(9) -0.0077(8) -0.0076(8) O4 0.0253(9) 0.0332(11) 0.0424(10) -0.0021(9) 0.0017(8) -0.0011(7) O5 0.0257(9) 0.0423(11) 0.0394(10) 0.0022(9) -0.0036(8) 0.0028(8) O6 0.0560(13) 0.069(2) 0.0359(10) -0.0015(11) -0.0050(9) 0.0080(11) O7 0.075(2) 0.159(3) 0.091(2) -0.051(2) -0.020(2) 0.039(2) C8 0.052(2) 0.076(3) 0.046(2) -0.003(2) 0.003(2) 0.000(2) C9 0.070(2) 0.094(3) 0.053(2) -0.006(2) -0.012(2) 0.001(2) C10 0.061(2) 0.107(3) 0.053(2) -0.007(2) -0.009(2) 0.002(2) C11 0.068(2) 0.100(3) 0.050(2) -0.003(2) -0.007(2) -0.006(2) C12 0.066(2) 0.122(4) 0.053(2) -0.007(2) -0.012(2) -0.005(2) C13 0.067(2) 0.109(3) 0.051(2) -0.004(2) -0.005(2) 0.000(2) C14 0.066(2) 0.119(4) 0.052(2) -0.007(2) -0.008(2) -0.002(2) C15 0.073(3) 0.111(3) 0.055(2) -0.004(2) -0.006(2) 0.005(2) C16 0.066(2) 0.096(3) 0.058(2) -0.003(2) -0.008(2) -0.004(2) C17 0.091(3) 0.146(4) 0.059(2) -0.012(3) -0.016(2) 0.024(3) C18 0.081(3) 0.143(5) 0.073(3) 0.007(3) -0.019(2) 0.003(3) _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 O1 1.403(3) . no C1 O5 1.413(3) . no C1 C2 1.525(3) . no C2 O2 1.433(3) . no C2 C3 1.525(3) . no C3 O3 1.430(3) . no C3 C4 1.537(3) . no C4 O4 1.425(3) . no C4 C5 1.528(3) . no C5 O5 1.445(3) . no C5 C6 1.504(4) . no C6 O6 1.450(3) . no C7 O1 1.440(3) . no O6 C8 1.334(4) . no O7 C8 1.200(4) . no C8 C9 1.494(5) . no C9 C10 1.515(4) . no C10 C11 1.525(5) . no C11 C12 1.521(5) . no C12 C13 1.515(5) . no C13 C14 1.512(4) . no C14 C15 1.508(5) . no C15 C16 1.521(5) . no C16 C17 1.489(5) . no C17 C18 1.509(5) . no 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 C1 O5 112.9(2) . . no O1 C1 C2 108.4(2) . . no O5 C1 C2 110.8(2) . . no O2 C2 C1 111.7(2) . . no O2 C2 C3 111.5(2) . . no C1 C2 C3 109.9(2) . . no O3 C3 C2 111.4(2) . . no O3 C3 C4 109.2(2) . . no C2 C3 C4 110.4(2) . . no O4 C4 C5 111.7(2) . . no O4 C4 C3 112.8(2) . . no C5 C4 C3 107.9(2) . . no O5 C5 C6 107.2(2) . . no O5 C5 C4 110.2(2) . . no C6 C5 C4 111.5(2) . . no O6 C6 C5 110.0(2) . . no C1 O1 C7 112.4(2) . . no C1 O5 C5 113.5(2) . . no C8 O6 C6 118.5(3) . . no O7 C8 O6 123.0(3) . . no O7 C8 C9 126.2(3) . . no O6 C8 C9 110.8(3) . . no C8 C9 C10 114.5(3) . . no C9 C10 C11 112.6(3) . . no C12 C11 C10 114.0(3) . . no C13 C12 C11 114.5(4) . . no C14 C13 C12 114.4(4) . . no C15 C14 C13 115.0(4) . . no C14 C15 C16 114.9(4) . . no C17 C16 C15 114.5(4) . . no C16 C17 C18 115.0(4) . . no 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 O1 C1 C2 O2 55.3(3) . . . . no O5 C1 C2 O2 179.6(2) . . . . no O1 C1 C2 C3 -69.0(2) . . . . no O5 C1 C2 C3 55.3(3) . . . . no O2 C2 C3 O3 59.4(3) . . . . no C1 C2 C3 O3 -176.2(2) . . . . no O2 C2 C3 C4 -179.2(2) . . . . no C1 C2 C3 C4 -54.8(3) . . . . no O3 C3 C4 O4 54.7(2) . . . . no C2 C3 C4 O4 -68.0(3) . . . . no O3 C3 C4 C5 178.7(2) . . . . no C2 C3 C4 C5 56.0(2) . . . . no O4 C4 C5 O5 66.6(3) . . . . no C3 C4 C5 O5 -58.0(3) . . . . no O4 C4 C5 C6 -52.3(3) . . . . no C3 C4 C5 C6 -176.9(2) . . . . no O5 C5 C6 O6 75.4(3) . . . . yes C4 C5 C6 O6 -164.0(2) . . . . yes O5 C1 O1 C7 69.9(3) . . . . no C2 C1 O1 C7 -167.1(2) . . . . no O1 C1 O5 C5 62.1(3) . . . . no C2 C1 O5 C5 -59.6(2) . . . . no C6 C5 O5 C1 -176.8(2) . . . . no C4 C5 O5 C1 61.7(3) . . . . no C5 C6 O6 C8 -120.2(3) . . . . yes C6 O6 C8 O7 3.8(5) . . . . no C6 O6 C8 C9 -175.0(3) . . . . yes O7 C8 C9 C10 -9.8(6) . . . . no O6 C8 C9 C10 168.9(3) . . . . no C8 C9 C10 C11 -170.8(3) . . . . no C9 C10 C11 C12 178.6(3) . . . . no C10 C11 C12 C13 -176.0(4) . . . . no C11 C12 C13 C14 -180.0(4) . . . . no C12 C13 C14 C15 -178.4(4) . . . . no C13 C14 C15 C16 179.0(4) . . . . no C14 C15 C16 C17 -179.5(4) . . . . no C15 C16 C17 C18 177.6(4) . . . . no _refine_diff_density_max 0.160 _refine_diff_density_min -0.167 _refine_diff_density_rms 0.044 #===END data_13 _audit_creation_ 99_06_01 _audit_creation_method SHELXL _chemical_name_systematic ; methyl 6-O-propanoyl-beta-D-glucopyranoside ; _chemical_name_common ? _chemical_formula_moiety 'C10 H18 O7' _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C10 H18 O7' _chemical_formula_weight 250.24 _chemical_melting_point ? _chemical_compound_source 114.85 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' '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 7.932(1) _cell_length_b 7.101(1) _cell_length_c 10.984(1) _cell_angle_alpha 90.00 _cell_angle_beta 101.11(1) _cell_angle_gamma 90.00 _cell_volume 607.0(1) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 8635 _cell_measurement_theta_min 1.89 _cell_measurement_theta_max 30.58 _exptl_crystal_description plate _exptl_crystal_colour clear _exptl_crystal_size_max .02 _exptl_crystal_size_mid .15 _exptl_crystal_size_min .3 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.369 _exptl_crystal_density_method ? _exptl_crystal_F_000 268 _exptl_absorpt_coefficient_mu 0.117 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.88 _exptl_absorpt_correction_T_max 1.00 _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Bruker SMART' _diffrn_measurement_method '\w scans' _diffrn_standards_number 50 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% -0.3 _diffrn_reflns_number 9051 _diffrn_reflns_av_R_equivalents 0.0236 _diffrn_reflns_av_sigmaI/netI 0.0256 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.89 _diffrn_reflns_theta_max 30.58 _reflns_number_total 3060 _reflns_number_observed 2738 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'Bruker SAINT' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement on F^2^ for ALL reflections except for 0 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.0495P)^2^+0.0821P] 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 noref _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 -0.04(89) _refine_ls_number_reflns 3060 _refine_ls_number_parameters 157 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0445 _refine_ls_R_factor_obs 0.0375 _refine_ls_wR_factor_all 0.0977 _refine_ls_wR_factor_obs 0.0932 _refine_ls_goodness_of_fit_all 1.068 _refine_ls_goodness_of_fit_obs 1.080 _refine_ls_restrained_S_all 1.068 _refine_ls_restrained_S_obs 1.080 _refine_ls_shift/esd_max 0.000 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group C1 C 0.4778(2) 0.3356(2) 0.14934(14) 0.0260(3) Uani 1 d . . H1A H 0.4524(2) 0.4038(2) 0.22125(14) 0.031 Uiso 1 calc R . C2 C 0.3227(2) 0.3388(2) 0.04321(13) 0.0270(3) Uani 1 d . . H2A H 0.3507(2) 0.2718(2) -0.02834(13) 0.032 Uiso 1 calc R . C3 C 0.1742(2) 0.2399(2) 0.08591(13) 0.0282(3) Uani 1 d . . H3A H 0.1353(2) 0.3190(2) 0.14818(13) 0.034 Uiso 1 calc R . C4 C 0.2244(2) 0.0476(2) 0.14319(12) 0.0285(3) Uani 1 d . . H4A H 0.2388(2) -0.0408(2) 0.07748(12) 0.034 Uiso 1 calc R . C5 C 0.3921(2) 0.0589(2) 0.23852(13) 0.0278(3) Uani 1 d . . H5A H 0.3747(2) 0.1351(2) 0.30943(13) 0.033 Uiso 1 calc R . C6 C 0.4563(2) -0.1341(2) 0.2829(2) 0.0399(4) Uani 1 d . . H6A H 0.3732(2) -0.1941(2) 0.3245(2) 0.048 Uiso 1 calc R . H6B H 0.4684(2) -0.2112(2) 0.2122(2) 0.048 Uiso 1 calc R . C7 C 0.7623(2) 0.4439(3) 0.2101(2) 0.0467(5) Uani 1 d . . H7A H 0.8553(2) 0.4996(3) 0.1784(2) 0.070 Uiso 1 calc R . H7B H 0.7983(2) 0.3247(3) 0.2475(2) 0.070 Uiso 1 calc R . H7C H 0.7296(2) 0.5258(3) 0.2711(2) 0.070 Uiso 1 calc R . O1 O 0.61769(12) 0.4161(2) 0.10998(10) 0.0345(3) Uani 1 d . . O2 O 0.27251(14) 0.5270(2) 0.00805(12) 0.0382(3) Uani 1 d . . H2 H 0.3377(20) 0.5715(11) -0.0513(16) 0.057 Uiso 1 calc R . O3 O 0.03696(13) 0.2223(2) -0.01867(10) 0.0380(3) Uani 1 d . . H3 H -0.0509(14) 0.1426(27) 0.0025(7) 0.057 Uiso 1 calc R . O4 O 0.0926(2) -0.0197(2) 0.20353(11) 0.0410(3) Uani 1 d . . H4 H 0.0288(20) -0.1169(24) 0.1542(11) 0.061 Uiso 1 calc R . O5 O 0.52067(12) 0.14474(15) 0.18125(9) 0.0289(2) Uani 1 d . . O6 O 0.6194(2) -0.1212(2) 0.36691(11) 0.0448(3) Uani 1 d . . O7 O 0.4852(2) -0.0610(3) 0.52517(13) 0.0660(5) Uani 1 d . . C8 C 0.6146(2) -0.0784(3) 0.4864(2) 0.0471(4) Uani 1 d . . C9 C 0.7930(3) -0.0534(4) 0.5615(2) 0.0626(6) Uani 1 d . . H9A H 0.7849(3) -0.0099(4) 0.6439(2) 0.075 Uiso 1 calc R . H9B H 0.8505(3) -0.1746(4) 0.5702(2) 0.075 Uiso 1 calc R . C10 C 0.8991(4) 0.0826(6) 0.5054(3) 0.0993(12) Uani 1 d . . H10A H 1.0109(4) 0.0926(6) 0.5572(3) 0.149 Uiso 1 calc R . H10B H 0.8445(4) 0.2039(6) 0.4982(3) 0.149 Uiso 1 calc R . H10C H 0.9101(4) 0.0391(6) 0.4245(3) 0.149 Uiso 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 C1 0.0247(6) 0.0237(7) 0.0305(6) 0.0016(5) 0.0071(5) -0.0003(5) C2 0.0251(6) 0.0253(7) 0.0308(6) 0.0023(5) 0.0058(5) 0.0015(5) C3 0.0245(6) 0.0294(7) 0.0308(6) 0.0002(6) 0.0055(5) -0.0006(5) C4 0.0303(6) 0.0291(7) 0.0268(6) -0.0007(6) 0.0077(5) -0.0049(6) C5 0.0306(6) 0.0262(7) 0.0270(6) 0.0023(6) 0.0068(5) -0.0015(5) C6 0.0499(9) 0.0281(9) 0.0401(8) 0.0047(7) 0.0046(7) -0.0005(7) C7 0.0297(7) 0.0580(12) 0.0482(9) 0.0110(9) -0.0027(6) -0.0101(8) O1 0.0250(4) 0.0430(7) 0.0352(5) 0.0098(5) 0.0049(4) -0.0063(4) O2 0.0296(5) 0.0303(6) 0.0551(6) 0.0144(5) 0.0093(5) 0.0042(4) O3 0.0262(5) 0.0432(7) 0.0419(6) 0.0061(5) 0.0001(4) -0.0054(5) O4 0.0400(6) 0.0464(8) 0.0386(6) 0.0014(5) 0.0130(5) -0.0157(5) O5 0.0262(4) 0.0275(5) 0.0333(5) 0.0038(4) 0.0068(4) 0.0016(4) O6 0.0442(6) 0.0459(8) 0.0437(6) 0.0126(6) 0.0072(5) 0.0102(6) O7 0.0604(8) 0.0913(14) 0.0489(8) 0.0059(9) 0.0170(7) 0.0079(9) C8 0.0509(9) 0.0468(11) 0.0412(8) 0.0155(8) 0.0029(7) 0.0052(8) C9 0.0533(11) 0.079(2) 0.0497(10) 0.0199(11) -0.0031(8) 0.0095(11) C10 0.0647(15) 0.137(3) 0.086(2) 0.042(2) -0.0111(13) -0.025(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 C1 O1 1.389(2) . no C1 O5 1.424(2) . no C1 C2 1.523(2) . no C2 O2 1.426(2) . no C2 C3 1.521(2) . no C3 O3 1.428(2) . no C3 C4 1.524(2) . no C4 O4 1.423(2) . no C4 C5 1.529(2) . no C5 O5 1.433(2) . no C5 C6 1.510(2) . no C6 O6 1.440(2) . no C7 O1 1.442(2) . no O6 C8 1.355(2) . no O7 C8 1.191(2) . no C8 C9 1.505(3) . no C9 C10 1.490(4) . no 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 C1 O5 107.52(11) . . no O1 C1 C2 109.35(11) . . no O5 C1 C2 108.78(11) . . no O2 C2 C3 108.89(11) . . no O2 C2 C1 111.31(11) . . no C3 C2 C1 108.43(11) . . no O3 C3 C2 107.96(11) . . no O3 C3 C4 110.56(12) . . no C2 C3 C4 112.65(11) . . no O4 C4 C3 109.67(12) . . no O4 C4 C5 108.60(11) . . no C3 C4 C5 111.05(11) . . no O5 C5 C6 107.68(12) . . no O5 C5 C4 108.70(10) . . no C6 C5 C4 111.60(13) . . no O6 C6 C5 110.76(13) . . no C1 O1 C7 112.62(11) . . no C1 O5 C5 110.87(10) . . no C8 O6 C6 116.47(14) . . no O7 C8 O6 123.8(2) . . no O7 C8 C9 125.2(2) . . no O6 C8 C9 111.0(2) . . no C10 C9 C8 113.3(2) . . no 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 O1 C1 C2 O2 -63.49(15) . . . . no O5 C1 C2 O2 179.36(11) . . . . no O1 C1 C2 C3 176.76(12) . . . . no O5 C1 C2 C3 59.60(14) . . . . no O2 C2 C3 O3 66.07(15) . . . . no C1 C2 C3 O3 -172.68(11) . . . . no O2 C2 C3 C4 -171.56(12) . . . . no C1 C2 C3 C4 -50.31(15) . . . . no O3 C3 C4 O4 -70.96(14) . . . . no C2 C3 C4 O4 168.15(11) . . . . no O3 C3 C4 C5 169.01(10) . . . . no C2 C3 C4 C5 48.12(15) . . . . no O4 C4 C5 O5 -174.11(13) . . . . no C3 C4 C5 O5 -53.44(15) . . . . no O4 C4 C5 C6 67.3(2) . . . . no C3 C4 C5 C6 -172.06(12) . . . . no O5 C5 C6 O6 57.4(2) . . . . yes C4 C5 C6 O6 176.59(12) . . . . yes O5 C1 O1 C7 -70.7(2) . . . . no C2 C1 O1 C7 171.34(13) . . . . no O1 C1 O5 C5 172.21(10) . . . . no C2 C1 O5 C5 -69.47(13) . . . . no C6 C5 O5 C1 -173.51(12) . . . . no C4 C5 O5 C1 65.44(14) . . . . no C5 C6 O6 C8 81.8(2) . . . . yes C6 O6 C8 O7 3.9(3) . . . . no C6 O6 C8 C9 -175.2(2) . . . . yes O7 C8 C9 C10 -126.5(3) . . . . no O6 C8 C9 C10 52.6(3) . . . . no _refine_diff_density_max 0.224 _refine_diff_density_min -0.171 _refine_diff_density_rms 0.042 #===END data_17 _audit_creation_ 99_06_01 _audit_creation_method SHELXL _chemical_name_systematic ; methyl 6-O-heptanoyl-beta-D-glucopyranoside ; _chemical_name_common ? _chemical_formula_moiety 'C14 H26 O7' _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C14 H26 O7' _chemical_formula_weight 306.35 _chemical_melting_point 67.4 _chemical_compound_source ? 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' '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 7.906(1) _cell_length_b 7.459(1) _cell_length_c 14.218(1) _cell_angle_alpha 90.00 _cell_angle_beta 102.63(1) _cell_angle_gamma 90.00 _cell_volume 818.2(1) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 8635 _cell_measurement_theta_min 1.47 _cell_measurement_theta_max 28.37 _exptl_crystal_description plate _exptl_crystal_colour clear _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.244 _exptl_crystal_density_method ? _exptl_crystal_F_000 332 _exptl_absorpt_coefficient_mu 0.099 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.627 _exptl_absorpt_correction_T_max 1.000 _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Bruker SMART' _diffrn_measurement_method '\w scans' _diffrn_standards_number 50 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% -0.4 _diffrn_reflns_number 5483 _diffrn_reflns_av_R_equivalents 0.0208 _diffrn_reflns_av_sigmaI/netI 0.0396 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.47 _diffrn_reflns_theta_max 28.33 _reflns_number_total 3501 _reflns_number_observed 2702 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'Bruker SAINT' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement on F^2^ for ALL reflections except for 0 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.0659P)^2^+0.0439P] 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 noref _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 0.34(117) _refine_ls_number_reflns 3501 _refine_ls_number_parameters 285 _refine_ls_number_restraints 21 _refine_ls_R_factor_all 0.0615 _refine_ls_R_factor_obs 0.0450 _refine_ls_wR_factor_all 0.1226 _refine_ls_wR_factor_obs 0.1112 _refine_ls_goodness_of_fit_all 1.026 _refine_ls_goodness_of_fit_obs 1.071 _refine_ls_restrained_S_all 1.068 _refine_ls_restrained_S_obs 1.124 _refine_ls_shift/esd_max 0.000 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group C1 C -0.1061(2) -0.0694(2) 0.39114(15) 0.0398(4) Uani 1 d . . H1A H -0.1693(2) -0.1375(2) 0.33555(15) 0.048 Uiso 1 calc R . C2 C -0.2036(2) -0.0746(2) 0.47187(15) 0.0400(4) Uani 1 d . . H2A H -0.1376(2) -0.0102(2) 0.52816(15) 0.048 Uiso 1 calc R . C3 C -0.3790(2) 0.0139(3) 0.43720(14) 0.0416(4) Uani 1 d . . H3A H -0.4509(2) -0.0635(3) 0.38874(14) 0.050 Uiso 1 calc R . C5 C -0.2501(3) 0.1894(3) 0.3198(2) 0.0491(5) Uani 1 d D . H5 H -0.3054(3) 0.1047(3) 0.2698(2) 0.059 Uiso 1 calc R 1 C4 C -0.3652(2) 0.1968(3) 0.39257(14) 0.0419(4) Uani 1 d . . H4A H -0.3166(2) 0.2826(3) 0.44353(14) 0.050 Uiso 1 calc R . C7 C 0.1500(3) -0.1614(3) 0.3467(2) 0.0573(6) Uani 1 d . . H7A H 0.2628(3) -0.2104(3) 0.3726(2) 0.086 Uiso 1 calc R . H7B H 0.1618(3) -0.0470(3) 0.3179(2) 0.086 Uiso 1 calc R . H7C H 0.0865(3) -0.2413(3) 0.2988(2) 0.086 Uiso 1 calc R . O1 O 0.0584(2) -0.1397(2) 0.42279(10) 0.0470(4) Uani 1 d . . O2 O -0.2311(2) -0.2552(2) 0.49759(12) 0.0552(4) Uani 1 d . . H2 H -0.1306(14) -0.2976(13) 0.5428(15) 0.083 Uiso 1 calc R . O3 O -0.4593(2) 0.0293(2) 0.51787(11) 0.0530(4) Uani 1 d . . H3 H -0.5494(26) 0.1179(29) 0.5043(9) 0.079 Uiso 1 calc R . O4 O -0.5327(2) 0.2555(2) 0.34425(12) 0.0614(4) Uani 1 d . . H4 H -0.5685(17) 0.3534(28) 0.3792(12) 0.092 Uiso 1 calc R . O5 O -0.0867(2) 0.1120(2) 0.36432(10) 0.0469(3) Uani 1 d . . C6A C -0.2370(14) 0.3649(11) 0.2687(6) 0.059(3) Uani 0.472(4) d PD 1 H6AA H -0.3500(14) 0.4211(11) 0.2502(6) 0.071 Uiso 0.472(4) calc PR 1 H6AB H -0.1591(14) 0.4463(11) 0.3105(6) 0.071 Uiso 0.472(4) calc PR 1 C8A C -0.0080(15) 0.3656(21) 0.1848(10) 0.082(4) Uani 0.472(4) d PD 1 C9A C 0.0378(13) 0.2844(14) 0.0979(7) 0.110(3) Uani 0.472(4) d PD 1 H9A1 H 0.0534(13) 0.1565(14) 0.1090(7) 0.132 Uiso 0.472(4) calc PR 1 H9A2 H -0.0600(13) 0.3000(14) 0.0440(7) 0.132 Uiso 0.472(4) calc PR 1 C10A C 0.1951(12) 0.3556(14) 0.0695(7) 0.087(2) Uani 0.472(4) d PD 1 H10A H 0.1818(12) 0.4841(14) 0.0603(7) 0.104 Uiso 0.472(4) calc PR 1 H10B H 0.2942(12) 0.3358(14) 0.1222(7) 0.104 Uiso 0.472(4) calc PR 1 C11A C 0.2327(12) 0.2763(13) -0.0188(7) 0.092(3) Uani 0.472(4) d PD 1 H11A H 0.1350(12) 0.2983(13) -0.0721(7) 0.111 Uiso 0.472(4) calc PR 1 H11B H 0.2446(12) 0.1475(13) -0.0103(7) 0.111 Uiso 0.472(4) calc PR 1 C12A C 0.3941(11) 0.3490(12) -0.0443(6) 0.080(2) Uani 0.472(4) d PD 1 H12A H 0.4909(11) 0.3337(12) 0.0102(6) 0.096 Uiso 0.472(4) calc PR 1 H12B H 0.3795(11) 0.4764(12) -0.0572(6) 0.096 Uiso 0.472(4) calc PR 1 C13A C 0.4354(10) 0.2569(11) -0.1317(4) 0.077(2) Uani 0.472(4) d PD 1 H13A H 0.4537(10) 0.1296(11) -0.1197(4) 0.093 Uiso 0.472(4) calc PR 1 H13B H 0.3412(10) 0.2728(11) -0.1875(4) 0.093 Uiso 0.472(4) calc PR 1 C14A C 0.5993(18) 0.3449(24) -0.1480(11) 0.126(5) Uani 0.472(4) d PD 1 H14A H 0.6317(18) 0.2913(24) -0.2029(11) 0.189 Uiso 0.472(4) calc PR 1 H14B H 0.6910(18) 0.3283(24) -0.0920(11) 0.189 Uiso 0.472(4) calc PR 1 H14C H 0.5791(18) 0.4707(24) -0.1594(11) 0.189 Uiso 0.472(4) calc PR 1 O6A O -0.1711(7) 0.3223(7) 0.1848(4) 0.0780(14) Uani 0.472(4) d PD 1 O7A O 0.0858(8) 0.4337(9) 0.2533(6) 0.128(3) Uani 0.472(4) d P 1 C6B C -0.1993(11) 0.3836(11) 0.2996(6) 0.058(2) Uani 0.528(4) d PD 2 H6BA H -0.2971(11) 0.4388(11) 0.2562(6) 0.069 Uiso 0.528(4) calc PR 2 H6BB H -0.1795(11) 0.4498(11) 0.3598(6) 0.069 Uiso 0.528(4) calc PR 2 C8B C -0.0514(11) 0.3307(14) 0.1720(5) 0.052(2) Uani 0.528(4) d PD 2 C9B C 0.1194(8) 0.3619(11) 0.1438(4) 0.083(2) Uani 0.528(4) d PD 2 H9B1 H 0.1446(8) 0.4893(11) 0.1477(4) 0.100 Uiso 0.528(4) calc PR 2 H9B2 H 0.2100(8) 0.3016(11) 0.1899(4) 0.100 Uiso 0.528(4) calc PR 2 C10B C 0.1241(9) 0.2976(13) 0.0449(5) 0.085(2) Uani 0.528(4) d PD 2 H10C H 0.0305(9) 0.3527(13) -0.0017(5) 0.102 Uiso 0.528(4) calc PR 2 H10D H 0.1075(9) 0.1687(13) 0.0414(5) 0.102 Uiso 0.528(4) calc PR 2 C11B C 0.2981(9) 0.3450(13) 0.0203(5) 0.088(2) Uani 0.528(4) d PD 2 H11C H 0.3104(9) 0.4744(13) 0.0226(5) 0.106 Uiso 0.528(4) calc PR 2 H11D H 0.3898(9) 0.2960(13) 0.0704(5) 0.106 Uiso 0.528(4) calc PR 2 C12B C 0.3267(11) 0.2816(12) -0.0756(6) 0.090(2) Uani 0.528(4) d PD 2 H12C H 0.2358(11) 0.3290(12) -0.1266(6) 0.108 Uiso 0.528(4) calc PR 2 H12D H 0.3195(11) 0.1518(12) -0.0782(6) 0.108 Uiso 0.528(4) calc PR 2 C13B C 0.5016(10) 0.3401(14) -0.0925(6) 0.104(3) Uani 0.528(4) d PD 2 H13C H 0.5024(10) 0.4701(14) -0.0946(6) 0.125 Uiso 0.528(4) calc PR 2 H13D H 0.5893(10) 0.3041(14) -0.0367(6) 0.125 Uiso 0.528(4) calc PR 2 C14B C 0.5564(17) 0.2730(17) -0.1804(7) 0.101(3) Uani 0.528(4) d PD 2 H14D H 0.6687(17) 0.3203(17) -0.1818(7) 0.151 Uiso 0.528(4) calc PR 2 H14E H 0.4741(17) 0.3112(17) -0.2369(7) 0.151 Uiso 0.528(4) calc PR 2 H14F H 0.5614(17) 0.1444(17) -0.1788(7) 0.151 Uiso 0.528(4) calc PR 2 O6B O -0.0481(4) 0.4040(4) 0.2587(2) 0.0587(10) Uani 0.528(4) d PD 2 O7B O -0.1781(5) 0.2663(8) 0.1226(3) 0.0934(15) Uani 0.528(4) d P 2 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 0.0294(9) 0.0368(10) 0.0548(10) -0.0008(8) 0.0127(8) 0.0019(7) C2 0.0307(8) 0.0376(11) 0.0544(10) 0.0028(9) 0.0149(8) -0.0004(7) C3 0.0289(8) 0.0427(10) 0.0563(11) -0.0008(9) 0.0159(8) 0.0002(8) C5 0.0490(11) 0.0477(12) 0.0551(11) 0.0071(9) 0.0212(9) 0.0114(9) C4 0.0354(9) 0.0414(11) 0.0504(11) -0.0002(8) 0.0122(8) 0.0069(8) C7 0.0467(11) 0.0641(15) 0.0693(13) 0.0016(12) 0.0304(10) 0.0117(11) O1 0.0310(7) 0.0538(9) 0.0599(8) 0.0041(6) 0.0183(6) 0.0087(6) O2 0.0353(7) 0.0436(9) 0.0907(11) 0.0175(7) 0.0223(7) 0.0030(6) O3 0.0399(8) 0.0539(9) 0.0730(9) 0.0093(7) 0.0293(7) 0.0099(6) O4 0.0445(8) 0.0676(11) 0.0709(10) 0.0061(8) 0.0102(7) 0.0220(8) O5 0.0398(7) 0.0406(7) 0.0660(9) 0.0074(7) 0.0237(6) 0.0044(6) C6A 0.066(5) 0.058(4) 0.058(5) 0.019(4) 0.023(4) 0.021(3) C8A 0.088(8) 0.052(5) 0.112(8) -0.019(4) 0.034(6) -0.025(5) C9A 0.119(7) 0.106(7) 0.125(7) -0.020(6) 0.069(6) -0.029(6) C10A 0.072(5) 0.094(6) 0.104(6) 0.001(5) 0.041(5) -0.011(4) C11A 0.124(7) 0.076(5) 0.086(5) -0.014(4) 0.041(5) -0.011(5) C12A 0.087(5) 0.075(5) 0.080(5) -0.001(4) 0.020(4) 0.008(4) C13A 0.100(5) 0.075(5) 0.053(3) -0.009(3) 0.011(3) 0.001(4) C14A 0.118(9) 0.144(13) 0.115(10) 0.002(8) 0.025(8) 0.015(8) O6A 0.081(3) 0.097(4) 0.063(3) 0.021(2) 0.031(2) 0.001(3) O7A 0.108(4) 0.125(5) 0.177(6) -0.061(5) 0.087(4) -0.037(4) C6B 0.062(4) 0.059(4) 0.054(4) 0.018(3) 0.018(4) 0.014(3) C8B 0.050(4) 0.053(5) 0.054(3) 0.007(3) 0.015(3) -0.009(3) C9B 0.067(3) 0.119(6) 0.072(3) -0.011(4) 0.035(3) -0.031(4) C10B 0.067(5) 0.103(6) 0.088(5) -0.010(4) 0.028(4) -0.026(4) C11B 0.087(5) 0.096(6) 0.091(5) -0.001(4) 0.040(4) -0.013(4) C12B 0.101(6) 0.088(6) 0.090(5) -0.009(4) 0.042(4) -0.011(4) C13B 0.107(6) 0.134(8) 0.084(5) -0.003(5) 0.047(5) -0.002(5) C14B 0.115(8) 0.123(9) 0.079(6) 0.018(5) 0.053(6) 0.035(6) O6B 0.066(2) 0.054(2) 0.062(2) 0.0073(14) 0.027(2) -0.009(2) O7B 0.071(3) 0.144(4) 0.068(3) -0.011(3) 0.021(2) -0.025(3) _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 O1 1.383(2) . no C1 O5 1.423(2) . no C1 C2 1.517(2) . no C2 O2 1.425(2) . no C2 C3 1.518(3) . no C3 O3 1.432(2) . no C3 C4 1.518(3) . no C5 O5 1.430(2) . no C5 C6A 1.511(8) . no C5 C4 1.522(3) . no C5 C6B 1.546(8) . no C4 O4 1.421(2) . no C7 O1 1.436(2) . no C6A O6A 1.438(8) . no C8A O7A 1.200(13) . no C8A O6A 1.329(8) . no C8A C9A 1.489(9) . no C9A C10A 1.487(8) . no C10A C11A 1.476(12) . no C11A C12A 1.502(8) . no C12A C13A 1.516(8) . no C13A C14A 1.515(9) . no C6B O6B 1.448(8) . no C8B O7B 1.191(9) . no C8B O6B 1.343(7) . no C8B C9B 1.508(7) . no C9B C10B 1.494(7) . no C10B C11B 1.533(7) . no C11B C12B 1.507(7) . no C12B C13B 1.518(8) . no C13B C14B 1.495(8) . no 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 C1 O5 107.38(14) . . no O1 C1 C2 110.0(2) . . no O5 C1 C2 109.27(14) . . no O2 C2 C1 110.48(15) . . no O2 C2 C3 108.37(15) . . no C1 C2 C3 108.81(15) . . no O3 C3 C2 108.0(2) . . no O3 C3 C4 110.4(2) . . no C2 C3 C4 112.50(15) . . no O5 C5 C6A 114.4(4) . . no O5 C5 C4 109.3(2) . . no C6A C5 C4 114.2(4) . . no O5 C5 C6B 102.4(4) . . no C4 C5 C6B 108.1(4) . . no O4 C4 C3 109.5(2) . . no O4 C4 C5 108.4(2) . . no C3 C4 C5 111.11(14) . . no C1 O1 C7 113.0(2) . . no C1 O5 C5 111.27(15) . . no O6A C6A C5 106.4(6) . . no O7A C8A O6A 122.0(9) . . no O7A C8A C9A 128.7(10) . . no O6A C8A C9A 108.3(8) . . no C10A C9A C8A 116.7(8) . . no C11A C10A C9A 115.1(9) . . no C10A C11A C12A 113.6(8) . . no C11A C12A C13A 112.4(8) . . no C14A C13A C12A 105.9(9) . . no C8A O6A C6A 118.3(8) . . no O6B C6B C5 116.3(6) . . no O7B C8B O6B 123.4(7) . . no O7B C8B C9B 126.3(6) . . no O6B C8B C9B 110.0(6) . . no C10B C9B C8B 114.1(6) . . no C9B C10B C11B 110.4(6) . . no C12B C11B C10B 117.0(7) . . no C11B C12B C13B 112.0(7) . . no C14B C13B C12B 118.4(9) . . no C8B O6B C6B 118.3(6) . . no 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 O1 C1 C2 O2 -64.7(2) . . . . no O5 C1 C2 O2 177.7(2) . . . . no O1 C1 C2 C3 176.4(2) . . . . no O5 C1 C2 C3 58.8(2) . . . . no O2 C2 C3 O3 67.4(2) . . . . no C1 C2 C3 O3 -172.39(15) . . . . no O2 C2 C3 C4 -170.5(2) . . . . no C1 C2 C3 C4 -50.4(2) . . . . no O3 C3 C4 O4 -71.3(2) . . . . no C2 C3 C4 O4 168.0(2) . . . . no O3 C3 C4 C5 169.0(2) . . . . no C2 C3 C4 C5 48.4(2) . . . . no O5 C5 C4 O4 -173.7(2) . . . . no C6A C5 C4 O4 56.8(5) . . . . no C6B C5 C4 O4 75.7(4) . . . . no O5 C5 C4 C3 -53.3(2) . . . . no C6A C5 C4 C3 177.2(5) . . . . no C6B C5 C4 C3 -164.0(4) . . . . no O5 C1 O1 C7 -69.1(2) . . . . no C2 C1 O1 C7 172.1(2) . . . . no O1 C1 O5 C5 173.0(2) . . . . no C2 C1 O5 C5 -67.7(2) . . . . no C6A C5 O5 C1 -166.5(4) . . . . no C4 C5 O5 C1 64.2(2) . . . . no C6B C5 O5 C1 178.6(4) . . . . no O5 C5 C6A O6A 70.3(7) . . . . yes C4 C5 C6A O6A -162.8(5) . . . . yes C6B C5 C6A O6A 122.8(25) . . . . no O7A C8A C9A C10A -27.7(23) . . . . no O6A C8A C9A C10A 163.8(11) . . . . no C8A C9A C10A C11A -177.9(11) . . . . no C9A C10A C11A C12A -179.0(8) . . . . no C10A C11A C12A C13A 176.4(8) . . . . no C11A C12A C13A C14A 179.8(10) . . . . no O7A C8A O6A C6A 2.2(20) . . . . no C9A C8A O6A C6A 171.6(9) . . . . yes C5 C6A O6A C8A -106.9(11) . . . . yes O5 C5 C6B O6B 44.9(6) . . . . yes C6A C5 C6B O6B -87.4(21) . . . . no C4 C5 C6B O6B 160.2(5) . . . . yes O7B C8B C9B C10B -2.1(14) . . . . no O6B C8B C9B C10B -175.5(7) . . . . no C8B C9B C10B C11B 176.6(8) . . . . no C9B C10B C11B C12B 177.2(8) . . . . no C10B C11B C12B C13B 178.8(8) . . . . no C11B C12B C13B C14B 174.3(9) . . . . no O7B C8B O6B C6B 8.1(13) . . . . no C9B C8B O6B C6B -178.2(6) . . . . yes C5 C6B O6B C8B 61.6(9) . . . . yes _refine_diff_density_max 0.138 _refine_diff_density_min -0.169 _refine_diff_density_rms 0.034 #===END data_19 _audit_creation_ 99_06_01 _audit_creation_method SHELXL _chemical_name_systematic ; methyl 6-O-nonanoyl-beta-D-glucopyranoside ; _chemical_name_common _chemical_formula_moiety 'C16 H30 O7' _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C16 H30 O7' _chemical_formula_weight 334.40 _chemical_melting_point 76.0 _chemical_compound_source ? 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' '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 7.922(1) _cell_length_b 7.450(1) _cell_length_c 15.815(1) _cell_angle_alpha 90.00 _cell_angle_beta 100.01(1) _cell_angle_gamma 90.00 _cell_volume 919.0(1) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 8635 _cell_measurement_theta_min 1.31 _cell_measurement_theta_max 26.36 _exptl_crystal_description plate _exptl_crystal_colour clear _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.208 _exptl_crystal_density_method ? _exptl_crystal_F_000 364 _exptl_absorpt_coefficient_mu 0.094 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.78 _exptl_absorpt_correction_T_max 1.00 _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Bruker SAMRT' _diffrn_measurement_method '\w scans' _diffrn_standards_number 50 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% -0.3 _diffrn_reflns_number 5034 _diffrn_reflns_av_R_equivalents 0.0225 _diffrn_reflns_av_sigmaI/netI 0.0496 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.31 _diffrn_reflns_theta_max 26.36 _reflns_number_total 3269 _reflns_number_observed 2419 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'Bruker SAINT' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement on F^2^ for ALL reflections except for 1 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.0538P)^2^+0.0401P] 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 noref _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0214(44) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 1.20(143) _refine_ls_number_reflns 3268 _refine_ls_number_parameters 322 _refine_ls_number_restraints 25 _refine_ls_R_factor_all 0.0776 _refine_ls_R_factor_obs 0.0500 _refine_ls_wR_factor_all 0.1322 _refine_ls_wR_factor_obs 0.1054 _refine_ls_goodness_of_fit_all 1.064 _refine_ls_goodness_of_fit_obs 1.111 _refine_ls_restrained_S_all 1.206 _refine_ls_restrained_S_obs 1.154 _refine_ls_shift/esd_max 0.000 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group C1 C -0.4707(3) -0.1902(3) -0.5972(2) 0.0392(6) Uani 1 d . . H1A H -0.4463(3) -0.1222(3) -0.6468(2) 0.047 Uiso 1 calc R . C2 C -0.3168(3) -0.1841(3) -0.5254(2) 0.0392(6) Uani 1 d . . H2A H -0.3435(3) -0.2481(3) -0.4752(2) 0.047 Uiso 1 calc R . C3 C -0.1661(3) -0.2744(4) -0.5559(2) 0.0408(6) Uani 1 d . . H3A H -0.1279(3) -0.1968(4) -0.5989(2) 0.049 Uiso 1 calc R . C4 C -0.2108(3) -0.4571(3) -0.5964(2) 0.0414(6) Uani 1 d . . H4A H -0.2238(3) -0.5432(3) -0.5511(2) 0.050 Uiso 1 calc R . C5 C -0.3768(3) -0.4508(3) -0.6612(2) 0.0478(7) Uani 1 d D . H5A H -0.3564(3) -0.3663(3) -0.7058(2) 0.057 Uiso 1 calc R 1 C7 C -0.7581(3) -0.0975(4) -0.6379(2) 0.0584(8) Uani 1 d . . H7A H -0.8526(3) -0.0478(4) -0.6151(2) 0.088 Uiso 1 calc R . H7B H -0.7901(3) -0.2124(4) -0.6632(2) 0.088 Uiso 1 calc R . H7C H -0.7279(3) -0.0183(4) -0.6808(2) 0.088 Uiso 1 calc R . O1 O -0.6131(2) -0.1188(2) -0.56957(11) 0.0472(5) Uani 1 d . . O2 O -0.2709(2) -0.0030(2) -0.50231(13) 0.0534(5) Uani 1 d . . H2 H -0.3318(30) 0.0359(14) -0.4581(14) 0.080 Uiso 1 calc R . O3 O -0.0290(2) -0.2898(3) -0.48415(13) 0.0526(5) Uani 1 d . . H3 H 0.0537(22) -0.3749(33) -0.4973(8) 0.079 Uiso 1 calc R . O4 O -0.0772(2) -0.5171(3) -0.63932(13) 0.0606(6) Uani 1 d . . H4 H -0.0152(29) -0.6127(33) -0.6071(12) 0.091 Uiso 1 calc R . O5 O -0.5100(2) -0.3716(2) -0.62156(11) 0.0463(5) Uani 1 d . . C6A C -0.4267(20) -0.6267(14) -0.7069(8) 0.070(5) Uani 0.449(5) d PD 1 H6A1 H -0.3269(20) -0.6848(14) -0.7225(8) 0.084 Uiso 0.449(5) calc PR 1 H6A2 H -0.4778(20) -0.7072(14) -0.6703(8) 0.084 Uiso 0.449(5) calc PR 1 C8A C -0.7133(16) -0.6253(32) -0.7854(12) 0.080(6) Uani 0.449(5) d PD 1 C9A C -0.8221(12) -0.5442(16) -0.8622(7) 0.088(3) Uani 0.449(5) d PD 1 H9A1 H -0.7668(12) -0.5640(16) -0.9115(7) 0.105 Uiso 0.449(5) calc PR 1 H9A2 H -0.8269(12) -0.4155(16) -0.8534(7) 0.105 Uiso 0.449(5) calc PR 1 C10A C -1.0029(12) -0.6145(15) -0.8830(8) 0.080(3) Uani 0.449(5) d PD 1 H10A H -0.9994(12) -0.7443(15) -0.8873(8) 0.096 Uiso 0.449(5) calc PR 1 H10B H -1.0626(12) -0.5847(15) -0.8363(8) 0.096 Uiso 0.449(5) calc PR 1 C11A C -1.0989(13) -0.5420(17) -0.9629(7) 0.079(3) Uani 0.449(5) d PD 1 H11A H -1.0365(13) -0.5682(17) -1.0091(7) 0.095 Uiso 0.449(5) calc PR 1 H11B H -1.1049(13) -0.4125(17) -0.9577(7) 0.095 Uiso 0.449(5) calc PR 1 C12A C -1.2803(12) -0.6153(14) -0.9871(7) 0.081(3) Uani 0.449(5) d PD 1 H12A H -1.2737(12) -0.7445(14) -0.9937(7) 0.098 Uiso 0.449(5) calc PR 1 H12B H -1.3411(12) -0.5923(14) -0.9401(7) 0.098 Uiso 0.449(5) calc PR 1 C13A C -1.3842(12) -0.5380(15) -1.0688(7) 0.078(3) Uani 0.449(5) d PD 1 H13A H -1.3889(12) -0.4086(15) -1.0629(7) 0.094 Uiso 0.449(5) calc PR 1 H13B H -1.3252(12) -0.5638(15) -1.1162(7) 0.094 Uiso 0.449(5) calc PR 1 C14A C -1.5650(11) -0.6092(13) -1.0904(6) 0.071(3) Uani 0.449(5) d PD 1 H14A H -1.6212(11) -0.5907(13) -1.0413(6) 0.085 Uiso 0.449(5) calc PR 1 H14B H -1.5598(11) -0.7376(13) -1.0999(6) 0.085 Uiso 0.449(5) calc PR 1 C15A C -1.6737(12) -0.5249(15) -1.1683(5) 0.076(3) Uani 0.449(5) d PD 1 H15A H -1.6182(12) -0.5444(15) -1.2176(5) 0.092 Uiso 0.449(5) calc PR 1 H15B H -1.6783(12) -0.3964(15) -1.1591(5) 0.092 Uiso 0.449(5) calc PR 1 C16A C -1.8578(17) -0.5969(31) -1.1895(12) 0.101(5) Uani 0.449(5) d PD 1 H16A H -1.9179(17) -0.5368(31) -1.2395(12) 0.151 Uiso 0.449(5) calc PR 1 H16B H -1.9154(17) -0.5753(31) -1.1418(12) 0.151 Uiso 0.449(5) calc PR 1 H16C H -1.8552(17) -0.7235(31) -1.2004(12) 0.151 Uiso 0.449(5) calc PR 1 O6A O -0.5493(8) -0.5819(9) -0.7831(4) 0.074(2) Uani 0.449(5) d PD 1 O7A O -0.7609(9) -0.6902(10) -0.7235(5) 0.117(3) Uani 0.449(5) d P 1 C6B C -0.4406(12) -0.6415(11) -0.6814(9) 0.053(3) Uani 0.550(5) d PD 2 H6B1 H -0.3748(12) -0.6930(11) -0.7217(9) 0.063 Uiso 0.550(5) calc PR 2 H6B2 H -0.4156(12) -0.7114(11) -0.6289(9) 0.063 Uiso 0.550(5) calc PR 2 C8B C -0.6806(12) -0.5897(19) -0.7936(6) 0.048(2) Uani 0.550(5) d PD 2 C9B C -0.8695(8) -0.6232(11) -0.8199(4) 0.069(2) Uani 0.550(5) d PD 2 H9B1 H -0.9282(8) -0.5712(11) -0.7767(4) 0.083 Uiso 0.550(5) calc PR 2 H9B2 H -0.8890(8) -0.7517(11) -0.8200(4) 0.083 Uiso 0.550(5) calc PR 2 C10B C -0.9493(9) -0.5497(12) -0.9061(5) 0.068(2) Uani 0.550(5) d PD 2 H10C H -0.8853(9) -0.5924(12) -0.9491(5) 0.081 Uiso 0.550(5) calc PR 2 H10D H -0.9420(9) -0.4197(12) -0.9047(5) 0.081 Uiso 0.550(5) calc PR 2 C11B C -1.1369(8) -0.6054(11) -0.9317(5) 0.064(2) Uani 0.550(5) d PD 2 H11C H -1.1419(8) -0.7355(11) -0.9323(5) 0.077 Uiso 0.550(5) calc PR 2 H11D H -1.1982(8) -0.5645(11) -0.8873(5) 0.077 Uiso 0.550(5) calc PR 2 C12B C -1.2317(9) -0.5381(12) -1.0171(4) 0.072(2) Uani 0.550(5) d PD 2 H12C H -1.1710(9) -0.5768(12) -1.0621(4) 0.086 Uiso 0.550(5) calc PR 2 H12D H -1.2319(9) -0.4079(12) -1.0166(4) 0.086 Uiso 0.550(5) calc PR 2 C13B C -1.4152(9) -0.6044(13) -1.0377(5) 0.072(2) Uani 0.550(5) d PD 2 H13C H -1.4732(9) -0.5689(13) -0.9912(5) 0.087 Uiso 0.550(5) calc PR 2 H13D H -1.4131(9) -0.7346(13) -1.0388(5) 0.087 Uiso 0.550(5) calc PR 2 C14B C -1.5220(9) -0.5395(12) -1.1216(5) 0.074(2) Uani 0.550(5) d PD 2 H14C H -1.5255(9) -0.4093(12) -1.1220(5) 0.089 Uiso 0.550(5) calc PR 2 H14D H -1.4689(9) -0.5783(12) -1.1694(5) 0.089 Uiso 0.550(5) calc PR 2 C15B C -1.7038(9) -0.6128(14) -1.1327(5) 0.087(2) Uani 0.550(5) d PD 2 H15C H -1.6999(9) -0.7426(14) -1.1368(5) 0.105 Uiso 0.550(5) calc PR 2 H15D H -1.7523(9) -0.5829(14) -1.0823(5) 0.105 Uiso 0.550(5) calc PR 2 C16B C -1.8197(15) -0.5395(22) -1.2119(7) 0.091(4) Uani 0.550(5) d PD 2 H16D H -1.9323(15) -0.5900(22) -1.2157(7) 0.136 Uiso 0.550(5) calc PR 2 H16E H -1.7738(15) -0.5710(22) -1.2622(7) 0.136 Uiso 0.550(5) calc PR 2 H16F H -1.8263(15) -0.4112(22) -1.2077(7) 0.136 Uiso 0.550(5) calc PR 2 O6B O -0.6214(5) -0.6635(5) -0.7167(2) 0.0558(12) Uani 0.550(5) d PD 2 O7B O -0.5883(7) -0.5214(8) -0.8376(4) 0.083(2) Uani 0.550(5) d P 2 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 0.0301(12) 0.0381(15) 0.0507(15) -0.0012(12) 0.0105(11) 0.0008(11) C2 0.0299(12) 0.039(2) 0.0500(14) -0.0039(12) 0.0104(11) -0.0002(11) C3 0.0266(11) 0.0467(14) 0.0492(15) 0.0032(12) 0.0072(11) 0.0013(11) C4 0.0342(13) 0.0445(15) 0.0469(15) 0.0021(12) 0.0113(11) 0.0073(11) C5 0.0428(15) 0.0466(15) 0.053(2) -0.0067(13) 0.0058(12) 0.0081(12) C7 0.0360(14) 0.067(2) 0.067(2) -0.006(2) -0.0034(13) 0.0090(14) O1 0.0288(8) 0.0556(11) 0.0569(11) -0.0055(9) 0.0073(8) 0.0057(8) O2 0.0332(10) 0.0459(11) 0.0830(14) -0.0178(10) 0.0152(9) -0.0040(8) O3 0.0309(9) 0.0564(11) 0.0685(12) -0.0086(10) 0.0027(8) 0.0085(8) O4 0.0511(12) 0.0674(13) 0.0669(12) -0.0038(11) 0.0202(10) 0.0209(11) O5 0.0349(9) 0.0422(9) 0.0596(11) -0.0065(9) 0.0021(8) 0.0009(8) C6A 0.065(7) 0.076(8) 0.064(9) -0.022(6) -0.002(6) 0.018(6) C8A 0.081(11) 0.054(8) 0.112(11) 0.006(6) 0.037(9) -0.018(7) C9A 0.080(7) 0.099(7) 0.081(7) 0.009(6) 0.007(6) -0.011(6) C10A 0.069(7) 0.077(7) 0.094(8) -0.006(6) 0.018(7) -0.014(5) C11A 0.090(9) 0.077(7) 0.075(7) 0.003(6) 0.026(7) -0.009(6) C12A 0.086(8) 0.068(6) 0.093(7) 0.003(5) 0.024(7) 0.002(5) C13A 0.093(9) 0.072(7) 0.073(7) 0.003(5) 0.024(7) 0.003(6) C14A 0.083(8) 0.072(6) 0.062(6) 0.001(5) 0.023(6) 0.004(5) C15A 0.093(8) 0.082(6) 0.055(5) 0.003(5) 0.015(6) 0.016(6) C16A 0.081(9) 0.136(14) 0.086(9) -0.013(8) 0.019(7) -0.012(8) O6A 0.068(4) 0.094(5) 0.054(4) -0.023(4) -0.002(3) -0.005(3) O7A 0.077(5) 0.123(6) 0.145(6) 0.055(5) -0.003(4) -0.008(4) C6B 0.048(4) 0.058(5) 0.049(5) -0.023(3) -0.002(4) 0.011(3) C8B 0.047(5) 0.047(7) 0.048(5) -0.009(3) 0.002(4) -0.008(4) C9B 0.047(4) 0.096(5) 0.063(4) 0.000(4) 0.002(3) -0.013(4) C10B 0.048(5) 0.081(6) 0.070(5) 0.006(4) 0.000(4) -0.011(4) C11B 0.049(4) 0.078(5) 0.061(5) -0.001(4) -0.003(4) -0.011(4) C12B 0.069(5) 0.074(5) 0.067(4) 0.006(4) -0.002(4) -0.012(4) C13B 0.063(5) 0.090(6) 0.059(5) 0.003(4) -0.002(4) -0.003(4) C14B 0.075(6) 0.091(6) 0.054(4) 0.012(4) 0.004(4) 0.002(4) C15B 0.079(6) 0.112(7) 0.065(5) 0.006(5) -0.005(4) -0.004(5) C16B 0.059(6) 0.129(11) 0.085(7) -0.029(7) 0.011(5) 0.003(6) O6B 0.053(3) 0.052(2) 0.058(2) -0.004(2) 0.000(2) -0.012(2) O7B 0.061(3) 0.122(4) 0.065(3) 0.010(3) 0.006(3) -0.021(3) _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 O1 1.385(3) . no C1 O5 1.425(3) . no C1 C2 1.516(3) . no C2 O2 1.428(3) . no C2 C3 1.520(3) . no C3 O3 1.433(3) . no C3 C4 1.519(3) . no C4 O4 1.425(3) . no C4 C5 1.520(3) . no C5 O5 1.444(3) . no C5 C6A 1.516(9) . no C5 C6B 1.523(8) . no C7 O1 1.442(3) . no C6A O6A 1.449(9) . no C8A O7A 1.21(2) . no C8A O6A 1.333(10) . no C8A C9A 1.490(10) . no C9A C10A 1.507(8) . no C10A C11A 1.460(15) . no C11A C12A 1.523(9) . no C12A C13A 1.519(9) . no C13A C14A 1.510(9) . no C14A C15A 1.512(8) . no C15A C16A 1.535(9) . no C6B O6B 1.453(8) . no C8B O7B 1.206(11) . no C8B O6B 1.343(8) . no C8B C9B 1.502(8) . no C9B C10B 1.504(7) . no C10B C11B 1.528(8) . no C11B C12B 1.512(7) . no C12B C13B 1.516(8) . no C13B C14B 1.523(8) . no C14B C15B 1.521(8) . no C15B C16B 1.520(9) . no 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 C1 O5 107.3(2) . . no O1 C1 C2 110.2(2) . . no O5 C1 C2 109.9(2) . . no O2 C2 C1 110.8(2) . . no O2 C2 C3 108.7(2) . . no C1 C2 C3 108.8(2) . . no O3 C3 C4 110.6(2) . . no O3 C3 C2 108.2(2) . . no C4 C3 C2 113.1(2) . . no O4 C4 C3 110.1(2) . . no O4 C4 C5 108.4(2) . . no C3 C4 C5 111.5(2) . . no O5 C5 C6A 114.2(7) . . no O5 C5 C4 109.4(2) . . no C6A C5 C4 114.7(5) . . no O5 C5 C6B 103.4(5) . . no C4 C5 C6B 109.2(4) . . no C1 O1 C7 113.1(2) . . no C1 O5 C5 111.3(2) . . no O6A C6A C5 106.2(7) . . no O7A C8A O6A 120.9(12) . . no O7A C8A C9A 127.2(11) . . no O6A C8A C9A 110.3(10) . . no C8A C9A C10A 115.5(10) . . no C11A C10A C9A 113.1(11) . . no C10A C11A C12A 114.3(10) . . no C13A C12A C11A 115.2(10) . . no C14A C13A C12A 114.4(9) . . no C13A C14A C15A 115.0(10) . . no C14A C15A C16A 114.7(13) . . no C8A O6A C6A 118.5(12) . . no O6B C6B C5 117.1(7) . . no O7B C8B O6B 122.9(8) . . no O7B C8B C9B 125.9(7) . . no O6B C8B C9B 110.9(8) . . no C8B C9B C10B 115.6(7) . . no C9B C10B C11B 112.2(7) . . no C12B C11B C10B 117.1(7) . . no C11B C12B C13B 113.1(7) . . no C12B C13B C14B 116.8(8) . . no C15B C14B C13B 110.9(8) . . no C16B C15B C14B 113.0(9) . . no C8B O6B C6B 117.9(8) . . no 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 O1 C1 C2 O2 -64.3(2) . . . . no O5 C1 C2 O2 177.7(2) . . . . no O1 C1 C2 C3 176.3(2) . . . . no O5 C1 C2 C3 58.2(2) . . . . no O2 C2 C3 O3 67.0(3) . . . . no C1 C2 C3 O3 -172.2(2) . . . . no O2 C2 C3 C4 -170.2(2) . . . . no C1 C2 C3 C4 -49.4(3) . . . . no O3 C3 C4 O4 -70.6(3) . . . . no C2 C3 C4 O4 167.9(2) . . . . no O3 C3 C4 C5 169.0(2) . . . . no C2 C3 C4 C5 47.5(3) . . . . no O4 C4 C5 O5 -173.7(2) . . . . no C3 C4 C5 O5 -52.3(3) . . . . no O4 C4 C5 C6A 56.4(8) . . . . no C3 C4 C5 C6A 177.8(8) . . . . no O4 C4 C5 C6B 73.9(6) . . . . no C3 C4 C5 C6B -164.8(6) . . . . no O5 C1 O1 C7 -68.4(3) . . . . no C2 C1 O1 C7 171.9(2) . . . . no O1 C1 O5 C5 173.0(2) . . . . no C2 C1 O5 C5 -67.2(2) . . . . no C6A C5 O5 C1 -166.6(5) . . . . no C4 C5 O5 C1 63.2(2) . . . . no C6B C5 O5 C1 179.5(5) . . . . no O5 C5 C6A O6A 71.1(12) . . . . yes C4 C5 C6A O6A -161.4(8) . . . . yes C6B C5 C6A O6A 123.9(36) . . . . no O7A C8A C9A C10A -27.1(31) . . . . no O6A C8A C9A C10A 167.3(14) . . . . no C8A C9A C10A C11A -175.0(14) . . . . no C9A C10A C11A C12A 178.1(9) . . . . no C10A C11A C12A C13A 178.4(9) . . . . no C11A C12A C13A C14A -178.6(9) . . . . no C12A C13A C14A C15A 176.2(8) . . . . no C13A C14A C15A C16A -179.5(12) . . . . no O7A C8A O6A C6A 4.6(30) . . . . no C9A C8A O6A C6A 171.3(12) . . . . yes C5 C6A O6A C8A -108.1(17) . . . . yes O5 C5 C6B O6B 42.5(10) . . . . yes C6A C5 C6B O6B -89.1(28) . . . . no C4 C5 C6B O6B 158.9(8) . . . . yes O7B C8B C9B C10B -5.3(18) . . . . no O6B C8B C9B C10B -178.8(8) . . . . yes C8B C9B C10B C11B 174.3(9) . . . . no C9B C10B C11B C12B 179.5(7) . . . . no C10B C11B C12B C13B 178.5(7) . . . . no C11B C12B C13B C14B 178.5(7) . . . . no C12B C13B C14B C15B -178.6(7) . . . . no C13B C14B C15B C16B 175.2(9) . . . . no O7B C8B O6B C6B 7.0(17) . . . . no C9B C8B O6B C6B -179.3(8) . . . . no C5 C6B O6B C8B 63.3(13) . . . . yes _refine_diff_density_max 0.175 _refine_diff_density_min -0.177 _refine_diff_density_rms 0.047 #===END data_21 _audit_creation_ 99_06_01 _audit_creation_method SHELXL _chemical_name_systematic ; methyl 6-O-undecanoyl-beta-D-glucopyranoside ; _chemical_name_common ? _chemical_formula_moiety 'C18 H34 O7' _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C18 H34 O7' _chemical_formula_weight 362.45 _chemical_melting_point 85.6 _chemical_compound_source ? 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' '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)/m loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 7.923(1) _cell_length_b 7.437(1) _cell_length_c 17.217(1) _cell_angle_alpha 90.00 _cell_angle_beta 92.626(1) _cell_angle_gamma 90.00 _cell_volume 1013.50(1) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 8536 _cell_measurement_theta_min 2.37 _cell_measurement_theta_max 24.69 _exptl_crystal_description plate _exptl_crystal_colour clear _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.188 _exptl_crystal_density_method ? _exptl_crystal_F_000 396 _exptl_absorpt_coefficient_mu 0.090 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.30 _exptl_absorpt_correction_T_max 1.00 _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Bruker SMART' _diffrn_measurement_method '\w scans' _diffrn_standards_number 50 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0.3 _diffrn_reflns_number 4339 _diffrn_reflns_av_R_equivalents 0.0423 _diffrn_reflns_av_sigmaI/netI 0.0627 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.37 _diffrn_reflns_theta_max 24.69 _reflns_number_total 2668 _reflns_number_observed 2167 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'Bruker SAINT' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement on F^2^ for ALL reflections except for 0 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.0812P)^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 noref _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0334(67) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 1.18(156) _refine_ls_number_reflns 2668 _refine_ls_number_parameters 358 _refine_ls_number_restraints 29 _refine_ls_R_factor_all 0.0600 _refine_ls_R_factor_obs 0.0508 _refine_ls_wR_factor_all 0.1319 _refine_ls_wR_factor_obs 0.1259 _refine_ls_goodness_of_fit_all 0.992 _refine_ls_goodness_of_fit_obs 1.068 _refine_ls_restrained_S_all 1.041 _refine_ls_restrained_S_obs 1.124 _refine_ls_shift/esd_max -0.085 _refine_ls_shift/esd_mean 0.003 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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group C1 C -1.0543(3) -0.3305(4) -0.9120(2) 0.0405(7) Uani 1 d . . H1A H -1.0919(3) -0.2620(4) -0.8674(2) 0.049 Uiso 1 calc R . C2 C -1.1888(3) -0.3257(4) -0.9771(2) 0.0406(7) Uani 1 d . . H2A H -1.1493(3) -0.3899(4) -1.0226(2) 0.049 Uiso 1 calc R . C3 C -1.3484(3) -0.4150(4) -0.9490(2) 0.0422(7) Uani 1 d . . H3A H -1.3975(3) -0.3372(4) -0.9100(2) 0.051 Uiso 1 calc R . C4 C -1.3134(3) -0.5980(4) -0.9129(2) 0.0425(7) Uani 1 d . . H4A H -1.2887(3) -0.6838(4) -0.9541(2) 0.051 Uiso 1 calc R . C5 C -1.1640(4) -0.5921(4) -0.8538(2) 0.0492(8) Uani 1 d D . H5 H -1.1964(4) -0.5051(4) -0.8144(2) 0.059 Uiso 1 calc R 1 C7 C -0.7774(4) -0.2365(5) -0.8752(2) 0.0587(9) Uani 1 d . . H7A H -0.6771(4) -0.1866(5) -0.8959(2) 0.088 Uiso 1 calc R . H7B H -0.7515(4) -0.3513(5) -0.8520(2) 0.088 Uiso 1 calc R . H7C H -0.8187(4) -0.1569(5) -0.8365(2) 0.088 Uiso 1 calc R . O1 O -0.9052(2) -0.2588(3) -0.93720(11) 0.0473(5) Uani 1 d . . O2 O -1.2293(2) -0.1432(3) -0.99756(13) 0.0545(6) Uani 1 d . . H2 H -1.1656(33) -0.1075(16) -1.0411(13) 0.082 Uiso 1 calc R . O3 O -1.4663(2) -0.4304(3) -1.01462(12) 0.0536(6) Uani 1 d . . H3 H -1.5502(28) -0.5190(37) -1.0038(9) 0.080 Uiso 1 calc R . O4 O -1.4584(3) -0.6583(3) -0.87388(12) 0.0606(6) Uani 1 d . . H4 H -1.5086(30) -0.7583(35) -0.9015(13) 0.091 Uiso 1 calc R . O5 O -1.0219(2) -0.5124(3) -0.88979(11) 0.0475(5) Uani 1 d . . C6A C -1.1344(19) -0.7667(15) -0.8101(6) 0.066(5) Uani 0.413(6) d PD 1 H6AA H -1.2404(19) -0.8161(15) -0.7938(6) 0.079 Uiso 0.413(6) calc PR 1 H6AB H -1.0806(19) -0.8544(15) -0.8426(6) 0.079 Uiso 0.413(6) calc PR 1 O6A O -1.0250(11) -0.7207(11) -0.7433(4) 0.067(2) Uani 0.413(6) d PD 1 O7A O -0.7958(11) -0.8324(14) -0.7961(5) 0.116(4) Uani 0.413(6) d P 1 C8A C -0.8612(19) -0.7632(41) -0.7430(13) 0.075(7) Uani 0.413(6) d PD 1 C9A C -0.7743(14) -0.6811(16) -0.6730(7) 0.082(3) Uani 0.413(6) d PD 1 H9A1 H -0.8424(14) -0.7023(16) -0.6285(7) 0.098 Uiso 0.413(6) calc PR 1 H9A2 H -0.7682(14) -0.5521(16) -0.6807(7) 0.098 Uiso 0.413(6) calc PR 1 C10A C -0.5968(14) -0.7520(18) -0.6545(7) 0.069(4) Uani 0.413(6) d PD 1 H10A H -0.6010(14) -0.8821(18) -0.6513(7) 0.083 Uiso 0.413(6) calc PR 1 H10B H -0.5255(14) -0.7208(18) -0.6968(7) 0.083 Uiso 0.413(6) calc PR 1 C11A C -0.5187(13) -0.6795(19) -0.5800(7) 0.071(4) Uani 0.413(6) d PD 1 H11A H -0.5918(13) -0.7075(19) -0.5380(7) 0.085 Uiso 0.413(6) calc PR 1 H11B H -0.5114(13) -0.5496(19) -0.5838(7) 0.085 Uiso 0.413(6) calc PR 1 C12A C -0.3434(14) -0.7543(17) -0.5600(6) 0.072(3) Uani 0.413(6) d PD 1 H12A H -0.3503(14) -0.8843(17) -0.5564(6) 0.087 Uiso 0.413(6) calc PR 1 H12B H -0.2699(14) -0.7256(17) -0.6018(6) 0.087 Uiso 0.413(6) calc PR 1 C13A C -0.2660(12) -0.6810(17) -0.4845(6) 0.065(4) Uani 0.413(6) d PD 1 H13A H -0.3388(12) -0.7109(17) -0.4426(6) 0.078 Uiso 0.413(6) calc PR 1 H13B H -0.2602(12) -0.5510(17) -0.4879(6) 0.078 Uiso 0.413(6) calc PR 1 C14A C -0.0899(12) -0.7541(16) -0.4649(6) 0.069(3) Uani 0.413(6) d PD 1 H14A H -0.0181(12) -0.7263(16) -0.5074(6) 0.082 Uiso 0.413(6) calc PR 1 H14B H -0.0964(12) -0.8840(16) -0.4608(6) 0.082 Uiso 0.413(6) calc PR 1 C15A C -0.0078(13) -0.6797(18) -0.3897(7) 0.073(4) Uani 0.413(6) d PD 1 H15A H -0.0032(13) -0.5497(18) -0.3933(7) 0.087 Uiso 0.413(6) calc PR 1 H15B H -0.0783(13) -0.7098(18) -0.3470(7) 0.087 Uiso 0.413(6) calc PR 1 C16A C 0.1701(14) -0.7508(16) -0.3713(6) 0.072(4) Uani 0.413(6) d PD 1 H16A H 0.1646(14) -0.8797(16) -0.3633(6) 0.086 Uiso 0.413(6) calc PR 1 H16B H 0.2386(14) -0.7293(16) -0.4157(6) 0.086 Uiso 0.413(6) calc PR 1 C17A C 0.2545(14) -0.6644(17) -0.3000(5) 0.072(3) Uani 0.413(6) d PD 1 H17A H 0.1840(14) -0.6823(17) -0.2561(5) 0.087 Uiso 0.413(6) calc PR 1 H17B H 0.2637(14) -0.5360(17) -0.3088(5) 0.087 Uiso 0.413(6) calc PR 1 C18A C 0.4305(21) -0.7406(29) -0.2800(13) 0.082(5) Uani 0.413(6) d PD 1 H18A H 0.4781(21) -0.6815(29) -0.2346(13) 0.122 Uiso 0.413(6) calc PR 1 H18B H 0.5018(21) -0.7210(29) -0.3228(13) 0.122 Uiso 0.413(6) calc PR 1 H18C H 0.4221(21) -0.8673(29) -0.2702(13) 0.122 Uiso 0.413(6) calc PR 1 C6B C -1.1039(10) -0.7818(10) -0.8351(6) 0.050(2) Uani 0.586(6) d PD 2 H6BA H -1.1798(10) -0.8331(10) -0.7984(6) 0.060 Uiso 0.586(6) calc PR 2 H6BB H -1.1159(10) -0.8523(10) -0.8824(6) 0.060 Uiso 0.586(6) calc PR 2 O6B O -0.9335(6) -0.8049(5) -0.8035(2) 0.0601(14) Uani 0.586(6) d PD 2 O7B O -0.9982(6) -0.6614(9) -0.6948(3) 0.086(2) Uani 0.586(6) d P 2 C8B C -0.8948(15) -0.7325(25) -0.7343(6) 0.052(3) Uani 0.586(6) d PD 2 C9B C -0.7132(9) -0.7641(11) -0.7107(4) 0.070(2) Uani 0.586(6) d PD 2 H9B1 H -0.6442(9) -0.7148(11) -0.7507(4) 0.084 Uiso 0.586(6) calc PR 2 H9B2 H -0.6935(9) -0.8928(11) -0.7090(4) 0.084 Uiso 0.586(6) calc PR 2 C10B C -0.6539(11) -0.6850(12) -0.6335(4) 0.068(3) Uani 0.586(6) d PD 2 H10C H -0.7293(11) -0.7230(12) -0.5939(4) 0.081 Uiso 0.586(6) calc PR 2 H10D H -0.6585(11) -0.5549(12) -0.6367(4) 0.081 Uiso 0.586(6) calc PR 2 C11B C -0.4751(9) -0.7429(12) -0.6103(5) 0.067(2) Uani 0.586(6) d PD 2 H11C H -0.4014(9) -0.7041(12) -0.6505(5) 0.081 Uiso 0.586(6) calc PR 2 H11D H -0.4719(9) -0.8732(12) -0.6089(5) 0.081 Uiso 0.586(6) calc PR 2 C12B C -0.4038(9) -0.6727(11) -0.5328(4) 0.067(2) Uani 0.586(6) d PD 2 H12C H -0.4780(9) -0.7085(11) -0.4923(4) 0.080 Uiso 0.586(6) calc PR 2 H12D H -0.4019(9) -0.5423(11) -0.5343(4) 0.080 Uiso 0.586(6) calc PR 2 C13B C -0.2256(9) -0.7410(12) -0.5120(5) 0.065(3) Uani 0.586(6) d PD 2 H13C H -0.2289(9) -0.8713(12) -0.5100(5) 0.078 Uiso 0.586(6) calc PR 2 H13D H -0.1530(9) -0.7076(12) -0.5535(5) 0.078 Uiso 0.586(6) calc PR 2 C14B C -0.1458(9) -0.6723(12) -0.4354(4) 0.069(2) Uani 0.586(6) d PD 2 H14C H -0.1399(9) -0.5421(12) -0.4372(4) 0.083 Uiso 0.586(6) calc PR 2 H14D H -0.2173(9) -0.7052(12) -0.3935(4) 0.083 Uiso 0.586(6) calc PR 2 C15B C 0.0296(9) -0.7467(13) -0.4184(5) 0.070(3) Uani 0.586(6) d PD 2 H15C H 0.0982(9) -0.7184(13) -0.4620(5) 0.083 Uiso 0.586(6) calc PR 2 H15D H 0.0216(9) -0.8766(13) -0.4154(5) 0.083 Uiso 0.586(6) calc PR 2 C16B C 0.1210(10) -0.6790(12) -0.3444(4) 0.068(2) Uani 0.586(6) d PD 2 H16C H 0.1284(10) -0.5489(12) -0.3466(4) 0.082 Uiso 0.586(6) calc PR 2 H16D H 0.0551(10) -0.7102(12) -0.3003(4) 0.082 Uiso 0.586(6) calc PR 2 C17B C 0.2970(10) -0.7557(14) -0.3320(5) 0.081(2) Uani 0.586(6) d PD 2 H17C H 0.3593(10) -0.7350(14) -0.3784(5) 0.098 Uiso 0.586(6) calc PR 2 H17D H 0.2887(10) -0.8847(14) -0.3247(5) 0.098 Uiso 0.586(6) calc PR 2 C18B C 0.3951(19) -0.6744(21) -0.2623(8) 0.085(4) Uani 0.586(6) d PD 2 H18D H 0.5053(19) -0.7280(21) -0.2573(8) 0.127 Uiso 0.586(6) calc PR 2 H18E H 0.3356(19) -0.6969(21) -0.2159(8) 0.127 Uiso 0.586(6) calc PR 2 H18F H 0.4062(19) -0.5471(21) -0.2696(8) 0.127 Uiso 0.586(6) calc PR 2 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 0.0321(15) 0.032(2) 0.057(2) 0.0007(13) 0.0047(12) -0.0025(12) C2 0.0305(14) 0.033(2) 0.0582(15) 0.0024(13) 0.0026(12) 0.0020(12) C3 0.0279(13) 0.041(2) 0.057(2) -0.0008(13) -0.0018(12) -0.0034(13) C4 0.035(2) 0.037(2) 0.056(2) -0.0005(13) 0.0032(12) -0.0083(13) C5 0.048(2) 0.041(2) 0.058(2) 0.0064(14) -0.0032(13) -0.0115(14) C7 0.037(2) 0.065(2) 0.074(2) 0.001(2) -0.0103(14) -0.010(2) O1 0.0266(9) 0.0484(13) 0.0665(12) 0.0046(9) -0.0013(8) -0.0062(9) O2 0.0317(11) 0.0402(13) 0.0912(15) 0.0163(11) 0.0002(9) 0.0034(10) O3 0.0319(10) 0.0506(13) 0.0773(13) 0.0086(11) -0.0091(9) -0.0078(10) O4 0.0476(13) 0.062(2) 0.0732(13) 0.0064(11) 0.0111(10) -0.0225(12) O5 0.0349(11) 0.0361(11) 0.0708(13) 0.0064(10) -0.0060(9) -0.0029(9) C6A 0.053(7) 0.081(9) 0.064(8) 0.020(6) 0.006(6) -0.019(6) O6A 0.066(5) 0.083(5) 0.051(5) 0.018(4) -0.004(4) 0.010(4) O7A 0.081(6) 0.132(8) 0.132(7) -0.064(6) -0.016(5) 0.022(6) C8A 0.057(10) 0.057(12) 0.111(15) -0.006(8) -0.001(11) 0.002(9) C9A 0.079(8) 0.078(8) 0.087(7) -0.008(7) -0.002(7) 0.005(6) C10A 0.054(7) 0.069(8) 0.083(8) 0.007(6) -0.002(8) 0.002(6) C11A 0.071(9) 0.067(8) 0.075(8) 0.000(6) 0.003(8) 0.004(6) C12A 0.073(8) 0.066(8) 0.077(7) 0.002(6) 0.000(7) -0.013(6) C13A 0.065(9) 0.063(7) 0.067(7) -0.005(6) 0.010(7) 0.000(5) C14A 0.062(7) 0.066(7) 0.079(7) -0.008(6) 0.005(7) -0.003(6) C15A 0.074(10) 0.070(8) 0.076(8) -0.010(6) 0.018(8) 0.003(6) C16A 0.081(11) 0.063(7) 0.073(7) -0.009(6) 0.019(8) -0.003(6) C17A 0.086(9) 0.069(7) 0.062(6) -0.001(5) 0.006(7) -0.011(6) C18A 0.072(10) 0.087(14) 0.084(9) 0.004(8) -0.003(7) -0.006(8) C6B 0.045(4) 0.046(4) 0.060(5) 0.017(3) -0.001(4) -0.011(3) O6B 0.062(3) 0.050(2) 0.068(3) 0.004(2) -0.007(2) 0.014(2) O7B 0.066(3) 0.122(5) 0.069(3) -0.017(3) -0.001(3) 0.030(3) C8B 0.057(7) 0.049(6) 0.051(5) 0.007(3) 0.001(5) 0.018(5) C9B 0.060(5) 0.083(5) 0.068(4) -0.005(4) 0.001(4) 0.014(4) C10B 0.060(6) 0.068(5) 0.075(5) -0.004(4) 0.002(5) 0.012(4) C11B 0.063(6) 0.070(6) 0.068(5) 0.003(4) 0.000(5) 0.009(4) C12B 0.065(5) 0.063(5) 0.072(5) -0.007(4) -0.003(5) 0.006(4) C13B 0.065(6) 0.069(6) 0.062(5) -0.006(4) 0.003(5) 0.000(4) C14B 0.069(6) 0.074(5) 0.065(4) -0.007(4) 0.002(5) -0.001(4) C15B 0.062(6) 0.078(7) 0.069(5) 0.006(4) 0.003(5) 0.009(4) C16B 0.072(6) 0.073(6) 0.060(5) 0.001(4) 0.000(5) 0.000(4) C17B 0.071(6) 0.094(7) 0.078(5) 0.000(5) -0.006(5) 0.008(5) C18B 0.074(7) 0.091(10) 0.088(8) 0.015(6) -0.009(6) -0.003(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 C1 O1 1.384(3) . no C1 O5 1.426(3) . no C1 C2 1.511(4) . no C2 O2 1.435(3) . no C2 C3 1.527(4) . no C3 O3 1.437(3) . no C3 C4 1.516(4) . no C4 O4 1.430(3) . no C4 C5 1.526(4) . no C5 O5 1.437(4) . no C5 C6A 1.514(10) . no C5 C6B 1.519(7) . no C7 O1 1.447(3) . no C6A O6A 1.450(10) . no O6A C8A 1.336(10) . no O7A C8A 1.19(2) . no C8A C9A 1.491(10) . no C9A C10A 1.522(9) . no C10A C11A 1.50(2) . no C11A C12A 1.521(9) . no C12A C13A 1.514(9) . no C13A C14A 1.520(9) . no C14A C15A 1.527(9) . no C15A C16A 1.525(9) . no C16A C17A 1.514(9) . no C17A C18A 1.530(10) . no C6B O6B 1.443(7) . no O6B C8B 1.331(9) . no O7B C8B 1.211(13) . no C8B C9B 1.495(9) . no C9B C10B 1.508(8) . no C10B C11B 1.517(9) . no C11B C12B 1.519(8) . no C12B C13B 1.527(8) . no C13B C14B 1.524(7) . no C14B C15B 1.512(8) . no C15B C16B 1.522(8) . no C16B C17B 1.513(8) . no C17B C18B 1.526(9) . no 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 C1 O5 107.7(2) . . no O1 C1 C2 110.0(2) . . no O5 C1 C2 109.5(2) . . no O2 C2 C1 110.3(2) . . no O2 C2 C3 108.0(2) . . no C1 C2 C3 108.7(2) . . no O3 C3 C4 110.5(2) . . no O3 C3 C2 107.7(2) . . no C4 C3 C2 112.4(2) . . no O4 C4 C3 109.7(2) . . no O4 C4 C5 108.1(2) . . no C3 C4 C5 111.6(2) . . no O5 C5 C6A 117.5(6) . . no O5 C5 C6B 103.3(4) . . no O5 C5 C4 108.9(2) . . no C6A C5 C4 113.8(5) . . no C6B C5 C4 109.9(4) . . no C1 O1 C7 113.0(2) . . no C1 O5 C5 111.8(2) . . no O6A C6A C5 105.4(7) . . no C8A O6A C6A 119.5(11) . . no O7A C8A O6A 123.9(13) . . no O7A C8A C9A 126.7(12) . . no O6A C8A C9A 108.5(11) . . no C8A C9A C10A 114.5(11) . . no C11A C10A C9A 113.3(12) . . no C10A C11A C12A 113.5(12) . . no C13A C12A C11A 113.1(11) . . no C12A C13A C14A 113.1(11) . . no C13A C14A C15A 114.2(10) . . no C16A C15A C14A 113.8(10) . . no C17A C16A C15A 113.0(11) . . no C16A C17A C18A 112.9(14) . . no O6B C6B C5 118.0(6) . . no C8B O6B C6B 117.5(8) . . no O7B C8B O6B 123.1(9) . . no O7B C8B C9B 125.7(8) . . no O6B C8B C9B 111.0(9) . . no C8B C9B C10B 115.8(8) . . no C9B C10B C11B 111.8(8) . . no C10B C11B C12B 116.1(8) . . no C11B C12B C13B 113.2(7) . . no C14B C13B C12B 115.7(8) . . no C15B C14B C13B 112.7(8) . . no C14B C15B C16B 116.0(8) . . no C17B C16B C15B 113.2(9) . . no C16B C17B C18B 113.3(11) . . no 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 O1 C1 C2 O2 -64.9(3) . . . . no O5 C1 C2 O2 177.0(2) . . . . no O1 C1 C2 C3 176.9(2) . . . . no O5 C1 C2 C3 58.8(3) . . . . no O2 C2 C3 O3 67.9(3) . . . . no C1 C2 C3 O3 -172.5(2) . . . . no O2 C2 C3 C4 -170.2(2) . . . . no C1 C2 C3 C4 -50.5(3) . . . . no O3 C3 C4 O4 -71.4(3) . . . . no C2 C3 C4 O4 168.3(2) . . . . no O3 C3 C4 C5 168.7(2) . . . . no C2 C3 C4 C5 48.4(3) . . . . no O4 C4 C5 O5 -173.5(2) . . . . no C3 C4 C5 O5 -52.7(3) . . . . no O4 C4 C5 C6A 53.4(7) . . . . no C3 C4 C5 C6A 174.2(7) . . . . no O4 C4 C5 C6B 74.0(5) . . . . no C3 C4 C5 C6B -165.2(5) . . . . no O5 C1 O1 C7 -68.6(3) . . . . no C2 C1 O1 C7 172.1(2) . . . . no O1 C1 O5 C5 172.9(2) . . . . no C2 C1 O5 C5 -67.5(3) . . . . no C6A C5 O5 C1 -165.6(5) . . . . no C6B C5 O5 C1 180.0(4) . . . . no C4 C5 O5 C1 63.2(3) . . . . no O5 C5 C6A O6A 67.3(11) . . . . yes C6B C5 C6A O6A 113.8(27) . . . . no C4 C5 C6A O6A -163.7(7) . . . . yes C5 C6A O6A C8A -104.0(20) . . . . yes C6A O6A C8A O7A 2.8(40) . . . . no C6A O6A C8A C9A 172.9(13) . . . . yes O7A C8A C9A C10A -23.6(39) . . . . no O6A C8A C9A C10A 166.6(17) . . . . no C8A C9A C10A C11A -174.8(17) . . . . no C9A C10A C11A C12A 178.3(9) . . . . no C10A C11A C12A C13A -179.7(9) . . . . no C11A C12A C13A C14A -179.4(9) . . . . no C12A C13A C14A C15A 179.0(9) . . . . no C13A C14A C15A C16A -178.8(9) . . . . no C14A C15A C16A C17A 175.4(9) . . . . no C15A C16A C17A C18A 178.0(13) . . . . no O5 C5 C6B O6B 42.3(8) . . . . yes C6A C5 C6B O6B -96.3(24) . . . . no C4 C5 C6B O6B 158.4(6) . . . . yes C5 C6B O6B C8B 63.8(13) . . . . yes C6B O6B C8B O7B 5.8(21) . . . . no C6B O6B C8B C9B -178.5(9) . . . . yes O7B C8B C9B C10B -5.5(22) . . . . no O6B C8B C9B C10B 179.0(10) . . . . no C8B C9B C10B C11B 173.1(10) . . . . no C9B C10B C11B C12B -179.2(6) . . . . no C10B C11B C12B C13B 178.2(7) . . . . no C11B C12B C13B C14B 178.9(6) . . . . no C12B C13B C14B C15B 179.5(7) . . . . no C13B C14B C15B C16B 177.7(7) . . . . no C14B C15B C16B C17B -178.7(7) . . . . no C15B C16B C17B C18B 174.4(9) . . . . no _refine_diff_density_max 0.358 _refine_diff_density_min -0.228 _refine_diff_density_rms 0.064 #===END