# Supplementary Material for Perkin Transactions # This journal is © The Royal Society of Chemistry 2001 data_shelxl _database_code_CSD 162741 _journal_coden_Cambridge 188 _publ_requested_journal 'Perkin Transactions 2' loop_ _publ_author_name 'Nagatomi, Eiji' 'Smith, John R. Lindsay' 'Stead, Angela' 'Waddington, D.' _publ_contact_author_name 'Prof John R Lindsay Smith' _publ_contact_author_address ; Prof John R Lindsay Smith Department of Chemistry University of York Heslington York Y01O 5DD UNITED KINGDOM ; _publ_contact_author_email 'JRLS1@YORK.AC.UK' _audit_creation_method SHELXL-97 _audit_creation_method SHELXL-97 _audit_contact_author_name 'Archibald, Stephen J.' _audit_contact_author_email 's.j.archibald@chem.hull.ac.uk' _chemical_name_systematic ; dineopentyl 2,3-diethylbutanedioate ; _chemical_formula_sum 'C18 H34 O4' _chemical_formula_weight 314.46 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 P21/a loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z' '-x, -y, -z' 'x-1/2, -y-1/2, z' _cell_length_a 8.359(5) _cell_length_b 13.505(4) _cell_length_c 9.538(4) _cell_angle_alpha 90.00 _cell_angle_beta 111.74(3) _cell_angle_gamma 90.00 _cell_volume 1000.1(8) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 20 _cell_measurement_theta_min 17.29 _cell_measurement_theta_max 19.02 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.2 _exptl_crystal_density_diffrn 1.044 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 348 _exptl_absorpt_coefficient_mu 0.072 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9179 _exptl_absorpt_correction_T_max 1.0000 _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type Rigaku-AFC6S _diffrn_measurement_method \w--2\q _diffrn_standards_number 3 _diffrn_standards_interval_count 150 _diffrn_standards_decay_% 1.7 _diffrn_reflns_number 1841 _diffrn_reflns_av_R_equivalents 0.012 _diffrn_reflns_av_sigmaI/netI 0.0305 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.30 _diffrn_reflns_theta_max 25.00 _reflns_number_total 1750 _reflns_number_gt 1216 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'MSC/AFC Diffractometer Control' _computing_cell_refinement 'MSC/AFC Diffractometer Control' _computing_data_reduction 'teXsan (MSC, 1992-1997)' _computing_structure_solution 'SIR-92' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP II (Johnson, 1976)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0624P)^2^+0.1845P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.023(4) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 1750 _refine_ls_number_parameters 101 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0725 _refine_ls_R_factor_gt 0.0400 _refine_ls_wR_factor_ref 0.1209 _refine_ls_wR_factor_gt 0.1047 _refine_ls_goodness_of_fit_ref 1.021 _refine_ls_restrained_S_all 1.021 _refine_ls_shift/su_max 0.007 _refine_ls_shift/su_mean 0.002 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.31787(14) 0.04544(9) 0.19346(13) 0.0373(4) Uani 1 1 d . . . O2 O 0.60499(15) 0.06166(10) 0.27863(14) 0.0451(4) Uani 1 1 d . . . C1 C 0.4604(2) -0.02926(12) 0.04819(18) 0.0330(4) Uani 1 1 d . . . H1 H 0.3363 -0.0423 -0.0133 0.040 Uiso 1 1 calc R . . C2 C 0.4723(2) 0.03135(13) 0.18531(19) 0.0329(4) Uani 1 1 d . . . C3 C 0.5519(2) -0.12853(13) 0.1028(2) 0.0416(5) Uani 1 1 d . . . H3A H 0.5563 -0.1656 0.0147 0.050 Uiso 1 1 calc R . . H3B H 0.6719 -0.1155 0.1715 0.050 Uiso 1 1 calc R . . C4 C 0.4638(3) -0.19258(16) 0.1847(3) 0.0598(6) Uani 1 1 d . . . H4A H 0.5276 -0.2547 0.2166 0.090 Uiso 1 1 calc R . . H4B H 0.3456 -0.2072 0.1166 0.090 Uiso 1 1 calc R . . H4C H 0.4614 -0.1571 0.2735 0.090 Uiso 1 1 calc R . . C5 C 0.3150(2) 0.09821(14) 0.32547(18) 0.0367(4) Uani 1 1 d . . . H5A H 0.3615 0.1659 0.3282 0.044 Uiso 1 1 calc R . . H5B H 0.3871 0.0631 0.4186 0.044 Uiso 1 1 calc R . . C6 C 0.1302(2) 0.10325(12) 0.31614(18) 0.0315(4) Uani 1 1 d . . . C7 C 0.1319(2) 0.15854(14) 0.4565(2) 0.0435(5) Uani 1 1 d . . . H7A H 0.0142 0.1634 0.4547 0.065 Uiso 1 1 calc R . . H7B H 0.1788 0.2252 0.4577 0.065 Uiso 1 1 calc R . . H7C H 0.2039 0.1225 0.5471 0.065 Uiso 1 1 calc R . . C8 C 0.0586(3) -0.00082(15) 0.3135(3) 0.0511(5) Uani 1 1 d . . . H8A H -0.0608 0.0033 0.3075 0.077 Uiso 1 1 calc R . . H8B H 0.1283 -0.0360 0.4059 0.077 Uiso 1 1 calc R . . H8C H 0.0624 -0.0367 0.2255 0.077 Uiso 1 1 calc R . . C9 C 0.0204(3) 0.16008(15) 0.1757(2) 0.0498(5) Uani 1 1 d . . . H9A H -0.0987 0.1630 0.1708 0.075 Uiso 1 1 calc R . . H9B H 0.0237 0.1264 0.0858 0.075 Uiso 1 1 calc R . . H9C H 0.0656 0.2275 0.1802 0.075 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0296(6) 0.0508(8) 0.0343(7) -0.0127(5) 0.0150(5) -0.0052(5) O2 0.0297(7) 0.0610(9) 0.0439(8) -0.0205(7) 0.0129(6) -0.0045(6) C1 0.0291(8) 0.0369(10) 0.0331(9) -0.0083(7) 0.0118(7) -0.0057(7) C2 0.0296(9) 0.0361(9) 0.0342(9) -0.0032(7) 0.0132(7) -0.0026(7) C3 0.0528(11) 0.0341(10) 0.0363(10) -0.0058(8) 0.0146(8) -0.0029(8) C4 0.0682(15) 0.0480(12) 0.0569(13) 0.0026(10) 0.0160(11) -0.0167(11) C5 0.0360(10) 0.0466(11) 0.0306(9) -0.0079(8) 0.0159(7) -0.0028(8) C6 0.0315(9) 0.0324(9) 0.0322(9) 0.0037(7) 0.0137(7) 0.0009(7) C7 0.0453(11) 0.0505(12) 0.0405(10) 0.0019(9) 0.0224(9) 0.0064(9) C8 0.0547(12) 0.0444(11) 0.0654(13) 0.0001(10) 0.0353(10) -0.0098(9) C9 0.0516(12) 0.0540(13) 0.0393(11) 0.0080(9) 0.0117(9) 0.0144(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C2 1.335(2) . ? O1 C5 1.455(2) . ? O2 C2 1.208(2) . ? C1 C2 1.515(2) . ? C1 C3 1.536(3) . ? C1 C1 1.536(3) 3_655 ? C3 C4 1.526(3) . ? C5 C6 1.515(2) . ? C6 C9 1.521(2) . ? C6 C8 1.524(3) . ? C6 C7 1.528(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 O1 C5 116.53(13) . . ? C2 C1 C3 108.30(14) . . ? C2 C1 C1 109.50(17) . 3_655 ? C3 C1 C1 112.38(17) . 3_655 ? O2 C2 O1 123.54(16) . . ? O2 C2 C1 124.62(15) . . ? O1 C2 C1 111.81(13) . . ? C4 C3 C1 113.22(17) . . ? O1 C5 C6 108.34(13) . . ? C5 C6 C9 110.09(15) . . ? C5 C6 C8 110.16(15) . . ? C9 C6 C8 110.24(16) . . ? C5 C6 C7 106.96(14) . . ? C9 C6 C7 109.37(15) . . ? C8 C6 C7 109.96(15) . . ? 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 C5 O1 C2 O2 -1.6(3) . . . . ? C5 O1 C2 C1 176.74(14) . . . . ? C3 C1 C2 O2 64.3(2) . . . . ? C1 C1 C2 O2 -58.5(3) 3_655 . . . ? C3 C1 C2 O1 -114.03(16) . . . . ? C1 C1 C2 O1 123.11(18) 3_655 . . . ? C2 C1 C3 C4 64.92(19) . . . . ? C1 C1 C3 C4 -173.99(17) 3_655 . . . ? C2 O1 C5 C6 -178.03(14) . . . . ? O1 C5 C6 C9 -61.54(19) . . . . ? O1 C5 C6 C8 60.24(18) . . . . ? O1 C5 C6 C7 179.73(13) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.194 _refine_diff_density_min -0.146 _refine_diff_density_rms 0.036