# Supplementary Material (ESI) for ChemComm # This journal is © The Royal Society of Chemistry 2000 # CCDC Number: 182/1839 data_C18H18O6 _audit_creation_date 'Oct 10 2000' _audit_creation_method 'by teXsan' #------------------------------------------------------------------------------ # CHEMICAL DATA _chemical_formula_sum 'C18 H18 O6 ' _chemical_formula_weight 330.34 #------------------------------------------------------------------------------ # CRYSTAL DATA _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/c 1' _symmetry_Int_Tables_number 14 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 8.1206(3) _cell_length_b 10.5914(3) _cell_length_c 19.7984(7) _cell_angle_alpha 90 _cell_angle_beta 100.513(1) _cell_angle_gamma 90 _cell_volume 1674.2(1) _cell_formula_units_Z 4 _cell_measurement_reflns_used 10119 _cell_measurement_theta_min 2.2 _cell_measurement_theta_max 27.5 _cell_measurement_temperature 296.2 #------------------------------------------------------------------------------ _exptl_crystal_description 'platelet' _exptl_crystal_colour 'yellow' _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.10 _exptl_crystal_size_rad ? _exptl_crystal_density_diffrn 1.310 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_absorpt_coefficient_mu 0.099 _exptl_absorpt_correction_type none #------------------------------------------------------------------------------ # EXPERIMENTAL DATA _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.7107 _diffrn_measurement_device_type 'Rigaku RAXIS-RAPID Imaging Plate' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 3845 _diffrn_reflns_av_R_equivalents 0.025 _diffrn_reflns_theta_max 27.49 _diffrn_measured_fraction_theta_max 0.9992 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.9992 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 #------------------------------------------------------------------------------ # REFINEMENT DATA _reflns_number_total 3845 _reflns_number_gt 2473 _reflns_threshold_expression F^2^>2\s(F^2^) _refine_ls_structure_factor_coef F _refine_ls_R_factor_gt 0.047 _refine_ls_wR_factor_ref 0.052 _refine_ls_hydrogen_treatment noref _refine_ls_number_reflns 2473 _refine_ls_number_parameters 217 _refine_ls_goodness_of_fit_ref 1.780 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[\s^2^(Fo) + 0.00031|Fo|^2^]' _refine_ls_shift/su_max 0.0006 _refine_diff_density_max 0.18 _refine_diff_density_min -0.19 _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details ? _refine_ls_abs_structure_Flack ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.003 0.002 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; 'H' 'H' 0.000 0.000 ;International Tables for Crystallography (1992, Vol. C, Table 6.1.1.2) ; 'O' 'O' 0.011 0.006 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; #------------------------------------------------------------------------------ # ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS 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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O(1) O 0.8868(2) 0.0339(1) 0.54989(7) 0.0632(4) Uani 1.00 d . . . O(2) O 0.9879(2) 0.1660(1) 0.63439(8) 0.0800(5) Uani 1.00 d . . . O(3) O 0.3919(2) 0.3156(1) 0.55240(7) 0.0649(4) Uani 1.00 d . . . O(4) O 0.5161(2) 0.4983(1) 0.58377(9) 0.0846(5) Uani 1.00 d . . . O(5) O 0.7610(2) 0.3517(1) 0.70515(7) 0.0692(4) Uani 1.00 d . . . O(6) O 0.9156(2) 0.4469(1) 0.63738(8) 0.0841(5) Uani 1.00 d . . . C(1) C 0.8830(2) 0.1416(2) 0.5855(1) 0.0573(6) Uani 1.00 d . . . C(2) C 0.7301(2) 0.2154(2) 0.55482(9) 0.0461(5) Uani 1.00 d . . . C(3) C 0.6567(2) 0.1496(2) 0.49174(8) 0.0434(5) Uani 1.00 d . . . C(4) C 0.7469(2) 0.0256(2) 0.49342(9) 0.0525(5) Uani 1.00 d . . . C(5) C 0.5476(2) 0.1976(2) 0.43868(9) 0.0464(5) Uani 1.00 d . . . C(6) C 0.4762(2) 0.1397(2) 0.37309(9) 0.0475(5) Uani 1.00 d . . . C(7) C 0.3984(3) 0.2183(2) 0.3205(1) 0.0643(6) Uani 1.00 d . . . C(8) C 0.3283(3) 0.1700(2) 0.2570(1) 0.0824(8) Uani 1.00 d . . . C(9) C 0.3307(3) 0.0424(2) 0.2451(1) 0.0800(8) Uani 1.00 d . . . C(10) C 0.4050(3) -0.0371(2) 0.2968(1) 0.0687(7) Uani 1.00 d . . . C(11) C 0.4773(2) 0.0100(2) 0.35987(9) 0.0559(5) Uani 1.00 d . . . C(12) C 0.6851(2) 0.3174(2) 0.58768(9) 0.0483(5) Uani 1.00 d . . . C(13) C 0.5233(2) 0.3874(2) 0.57315(9) 0.0510(5) Uani 1.00 d . . . C(14) C 0.2280(3) 0.3789(2) 0.5391(1) 0.0878(8) Uani 1.00 d . . . C(15) C 0.1201(3) 0.3166(2) 0.4823(1) 0.0825(8) Uani 1.00 d . . . C(16) C 0.8042(3) 0.3788(2) 0.6460(1) 0.0560(6) Uani 1.00 d . . . C(17) C 0.8598(3) 0.4073(3) 0.7670(1) 0.0896(8) Uani 1.00 d . . . C(18) C 0.9010(4) 0.3078(3) 0.8190(1) 0.110(1) Uani 1.00 d . . . H(1) H 0.7854 0.0123 0.4515 0.0630 Uiso 1.00 calc . . . H(2) H 0.6747 -0.0417 0.5007 0.0630 Uiso 1.00 calc . . . H(3) H 0.5118 0.2815 0.4449 0.0556 Uiso 1.00 calc . . . H(4) H 0.3934 0.3066 0.3284 0.0772 Uiso 1.00 calc . . . H(5) H 0.2781 0.2254 0.2214 0.0989 Uiso 1.00 calc . . . H(6) H 0.2814 0.0092 0.2015 0.0960 Uiso 1.00 calc . . . H(7) H 0.4063 -0.1255 0.2888 0.0825 Uiso 1.00 calc . . . H(8) H 0.5287 -0.0461 0.3949 0.0671 Uiso 1.00 calc . . . H(9) H 0.1786 0.3744 0.5790 0.1054 Uiso 1.00 calc . . . H(10) H 0.2422 0.4649 0.5278 0.1054 Uiso 1.00 calc . . . H(11) H 0.0140 0.3572 0.4736 0.0990 Uiso 1.00 calc . . . H(12) H 0.1696 0.3212 0.4424 0.0990 Uiso 1.00 calc . . . H(13) H 0.1060 0.2306 0.4936 0.0990 Uiso 1.00 calc . . . H(14) H 0.9599 0.4424 0.7566 0.1075 Uiso 1.00 calc . . . H(15) H 0.7968 0.4717 0.7840 0.1075 Uiso 1.00 calc . . . H(16) H 0.8006 0.2727 0.8291 0.1319 Uiso 1.00 calc . . . H(17) H 0.9640 0.2435 0.8019 0.1319 Uiso 1.00 calc . . . H(18) H 0.9652 0.3427 0.8596 0.1319 Uiso 1.00 calc . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 O(1) 0.0530(8) 0.0669(9) 0.0657(9) 0.0195(7) 0.0004(6) 0.0006(7) O(2) 0.0619(9) 0.097(1) 0.0702(9) 0.0122(8) -0.0176(8) -0.0015(9) O(3) 0.0460(7) 0.0556(8) 0.091(1) 0.0027(6) 0.0076(7) -0.0176(7) O(4) 0.082(1) 0.0462(8) 0.116(1) 0.0073(7) -0.0060(9) -0.0093(9) O(5) 0.0699(9) 0.088(1) 0.0463(8) -0.0177(8) 0.0017(6) -0.0119(7) O(6) 0.082(1) 0.091(1) 0.076(1) -0.0368(10) 0.0024(8) -0.0053(9) C(1) 0.047(1) 0.067(1) 0.055(1) 0.0038(9) 0.0031(9) 0.008(1) C(2) 0.0449(10) 0.0451(10) 0.0465(10) 0.0011(8) 0.0034(8) 0.0071(8) C(3) 0.0429(9) 0.0421(9) 0.0452(9) 0.0013(8) 0.0080(7) 0.0020(8) C(4) 0.0474(10) 0.052(1) 0.057(1) 0.0074(9) 0.0065(9) 0.0001(9) C(5) 0.050(1) 0.0407(9) 0.0477(10) 0.0035(8) 0.0077(8) -0.0004(8) C(6) 0.0445(10) 0.0516(10) 0.0462(10) -0.0003(8) 0.0081(8) -0.0016(8) C(7) 0.072(1) 0.060(1) 0.054(1) 0.003(1) -0.007(1) 0.003(1) C(8) 0.097(2) 0.083(2) 0.057(1) -0.002(1) -0.013(1) 0.008(1) C(9) 0.090(2) 0.093(2) 0.051(1) -0.015(1) -0.001(1) -0.011(1) C(10) 0.083(1) 0.061(1) 0.061(1) -0.012(1) 0.012(1) -0.014(1) C(11) 0.063(1) 0.053(1) 0.051(1) -0.0025(10) 0.0072(9) -0.0020(9) C(12) 0.049(1) 0.048(1) 0.045(1) -0.0025(8) 0.0017(8) 0.0050(8) C(13) 0.059(1) 0.047(1) 0.045(1) 0.0020(9) 0.0026(8) -0.0016(9) C(14) 0.048(1) 0.084(2) 0.128(2) 0.012(1) 0.006(1) -0.031(2) C(15) 0.063(1) 0.086(2) 0.093(2) 0.016(1) 0.001(1) 0.012(1) C(16) 0.056(1) 0.056(1) 0.053(1) -0.0048(10) -0.0004(9) -0.0027(9) C(17) 0.095(2) 0.112(2) 0.055(1) -0.018(2) -0.004(1) -0.027(1) C(18) 0.105(2) 0.147(3) 0.065(2) 0.009(2) -0.018(1) -0.011(2) #------------------------------------------------------------------------------ loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 O(1) C(1) 1.344(2) . . O(1) C(4) 1.444(2) . . O(2) C(1) 1.196(2) . . O(3) C(13) 1.314(2) . . O(3) C(14) 1.470(3) . . O(4) C(13) 1.196(2) . . O(5) C(16) 1.313(2) . . O(5) C(17) 1.460(2) . . O(6) C(16) 1.193(2) . . C(1) C(2) 1.499(3) . . C(2) C(3) 1.460(2) . . C(2) C(12) 1.345(2) . . C(3) C(4) 1.501(2) . . C(3) C(5) 1.344(2) . . C(5) C(6) 1.457(2) . . C(6) C(7) 1.392(3) . . C(6) C(11) 1.400(3) . . C(7) C(8) 1.379(3) . . C(8) C(9) 1.373(3) . . C(9) C(10) 1.377(3) . . C(10) C(11) 1.372(3) . . C(12) C(13) 1.490(3) . . C(12) C(16) 1.512(3) . . C(14) C(15) 1.453(3) . . C(17) C(18) 1.469(4) . . #------------------------------------------------------------------------------ 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_2 _geom_angle_site_symmetry_3 C(1) O(1) C(4) 111.5(1) . 1_555 1_555 C(13) O(3) C(14) 116.7(2) . 1_555 1_555 C(16) O(5) C(17) 117.7(2) . 1_555 1_555 O(1) C(1) O(2) 121.8(2) . 1_555 1_555 O(1) C(1) C(2) 109.1(2) . 1_555 1_555 O(2) C(1) C(2) 129.1(2) . 1_555 1_555 C(1) C(2) C(3) 106.0(2) . 1_555 1_555 C(1) C(2) C(12) 120.1(2) . 1_555 1_555 C(3) C(2) C(12) 133.9(2) . 1_555 1_555 C(2) C(3) C(4) 106.1(1) . 1_555 1_555 C(2) C(3) C(5) 126.6(2) . 1_555 1_555 C(4) C(3) C(5) 126.7(2) . 1_555 1_555 O(1) C(4) C(3) 106.0(1) . 1_555 1_555 C(3) C(5) C(6) 129.5(2) . 1_555 1_555 C(5) C(6) C(7) 117.9(2) . 1_555 1_555 C(5) C(6) C(11) 124.4(2) . 1_555 1_555 C(7) C(6) C(11) 117.7(2) . 1_555 1_555 C(6) C(7) C(8) 121.0(2) . 1_555 1_555 C(7) C(8) C(9) 120.4(2) . 1_555 1_555 C(8) C(9) C(10) 119.4(2) . 1_555 1_555 C(9) C(10) C(11) 120.8(2) . 1_555 1_555 C(6) C(11) C(10) 120.7(2) . 1_555 1_555 C(2) C(12) C(13) 127.9(2) . 1_555 1_555 C(2) C(12) C(16) 121.5(2) . 1_555 1_555 C(13) C(12) C(16) 110.6(2) . 1_555 1_555 O(3) C(13) O(4) 124.1(2) . 1_555 1_555 O(3) C(13) C(12) 114.2(1) . 1_555 1_555 O(4) C(13) C(12) 121.6(2) . 1_555 1_555 O(3) C(14) C(15) 109.3(2) . 1_555 1_555 O(5) C(16) O(6) 126.4(2) . 1_555 1_555 O(5) C(16) C(12) 110.4(2) . 1_555 1_555 O(6) C(16) C(12) 123.1(2) . 1_555 1_555 O(5) C(17) C(18) 108.6(2) . 1_555 1_555 #------------------------------------------------------------------------------ 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 O(1) C(1) C(2) C(3) -7.9(2) 1_555 1_555 1_555 1_555 O(1) C(1) C(2) C(12) 169.9(2) 1_555 1_555 1_555 1_555 O(1) C(4) C(3) C(2) -10.1(2) 1_555 1_555 1_555 1_555 O(1) C(4) C(3) C(5) 161.4(2) 1_555 1_555 1_555 1_555 O(2) C(1) O(1) C(4) 179.7(2) 1_555 1_555 1_555 1_555 O(2) C(1) C(2) C(3) 174.0(2) 1_555 1_555 1_555 1_555 O(2) C(1) C(2) C(12) -8.2(3) 1_555 1_555 1_555 1_555 O(3) C(13) C(12) C(2) 34.9(3) 1_555 1_555 1_555 1_555 O(3) C(13) C(12) C(16) -146.7(2) 1_555 1_555 1_555 1_555 O(4) C(13) O(3) C(14) 2.6(3) 1_555 1_555 1_555 1_555 O(4) C(13) C(12) C(2) -149.2(2) 1_555 1_555 1_555 1_555 O(4) C(13) C(12) C(16) 29.1(3) 1_555 1_555 1_555 1_555 O(5) C(16) C(12) C(2) -105.5(2) 1_555 1_555 1_555 1_555 O(5) C(16) C(12) C(13) 76.0(2) 1_555 1_555 1_555 1_555 O(6) C(16) O(5) C(17) -1.5(3) 1_555 1_555 1_555 1_555 O(6) C(16) C(12) C(2) 77.9(3) 1_555 1_555 1_555 1_555 O(6) C(16) C(12) C(13) -100.5(2) 1_555 1_555 1_555 1_555 C(1) O(1) C(4) C(3) 5.4(2) 1_555 1_555 1_555 1_555 C(1) C(2) C(3) C(4) 10.9(2) 1_555 1_555 1_555 1_555 C(1) C(2) C(3) C(5) -160.7(2) 1_555 1_555 1_555 1_555 C(1) C(2) C(12) C(13) -167.2(2) 1_555 1_555 1_555 1_555 C(1) C(2) C(12) C(16) 14.6(3) 1_555 1_555 1_555 1_555 C(2) C(1) O(1) C(4) 1.5(2) 1_555 1_555 1_555 1_555 C(2) C(3) C(5) C(6) 176.5(2) 1_555 1_555 1_555 1_555 C(3) C(2) C(12) C(13) 9.9(3) 1_555 1_555 1_555 1_555 C(3) C(2) C(12) C(16) -168.3(2) 1_555 1_555 1_555 1_555 C(3) C(5) C(6) C(7) -164.7(2) 1_555 1_555 1_555 1_555 C(3) C(5) C(6) C(11) 16.8(3) 1_555 1_555 1_555 1_555 C(4) C(3) C(2) C(12) -166.6(2) 1_555 1_555 1_555 1_555 C(4) C(3) C(5) C(6) 6.7(3) 1_555 1_555 1_555 1_555 C(5) C(3) C(2) C(12) 21.9(3) 1_555 1_555 1_555 1_555 C(5) C(6) C(7) C(8) 179.9(2) 1_555 1_555 1_555 1_555 C(5) C(6) C(11) C(10) 179.0(2) 1_555 1_555 1_555 1_555 C(6) C(7) C(8) C(9) 1.5(4) 1_555 1_555 1_555 1_555 C(6) C(11) C(10) C(9) 0.4(3) 1_555 1_555 1_555 1_555 C(7) C(6) C(11) C(10) 0.5(3) 1_555 1_555 1_555 1_555 C(7) C(8) C(9) C(10) -0.6(4) 1_555 1_555 1_555 1_555 C(8) C(7) C(6) C(11) -1.5(3) 1_555 1_555 1_555 1_555 C(8) C(9) C(10) C(11) -0.4(4) 1_555 1_555 1_555 1_555 C(12) C(13) O(3) C(14) 178.3(2) 1_555 1_555 1_555 1_555 C(12) C(16) O(5) C(17) -177.9(2) 1_555 1_555 1_555 1_555 C(13) O(3) C(14) C(15) 145.8(2) 1_555 1_555 1_555 1_555 C(16) O(5) C(17) C(18) -132.7(2) 1_555 1_555 1_555 1_555 #------------------------------------------------------------------------------