# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2003 data_global _publ_contact_author_email D.W.YOUNG@SUSSEX.AC.UK _publ_contact_author_name 'Dr Douglas W Young' _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 _journal_year ? _journal_volume ? _journal_page_first ? _publ_requested_category FO loop_ _publ_author_name D.W.Young P.B.Hitchcock S.Rahman data_apr396 _database_code_CSD 209172 _audit_creation_date 2003-06-06T11:07:40-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.2 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C18 H25 N1 O7' _chemical_formula_sum 'C18 H25 N1 O7' _chemical_formula_weight 367.39 _chemical_compound_source 'synthesis as described' _chemical_absolute_configuration syn #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting hexagonal _symmetry_space_group_name_H-M P6(1) _symmetry_space_group_name_Hall 'P 61' _symmetry_Int_Tables_number 169 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z+1/3' '-x+y, -x, z+2/3' '-x, -y, z+1/2' 'y, -x+y, z-1/6' 'x-y, x, z+1/6' _cell_length_a 8.994(2) _cell_length_b 8.994(2) _cell_length_c 43.134(6) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 120 _cell_volume 3021.7(10) _cell_formula_units_Z 6 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 7 _cell_measurement_theta_max 10 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.05 _exptl_crystal_density_diffrn 1.211 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1176 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.093 _exptl_absorpt_correction_type none #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_reflns_av_R_equivalents 0.0837 _diffrn_reflns_av_unetI/netI 0.0796 _diffrn_reflns_number 2787 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 45 _diffrn_reflns_theta_min 2.61 _diffrn_reflns_theta_max 21.98 _diffrn_reflns_theta_full 21.98 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _reflns_number_total 1259 _reflns_number_gt 1031 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0742P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_number_reflns 1259 _refine_ls_number_parameters 242 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0616 _refine_ls_R_factor_gt 0.0451 _refine_ls_wR_factor_ref 0.1198 _refine_ls_wR_factor_gt 0.1081 _refine_ls_goodness_of_fit_ref 0.968 _refine_ls_restrained_S_all 0.968 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 1(2) _refine_diff_density_max 0.158 _refine_diff_density_min -0.148 _refine_diff_density_rms 0.035 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 0.3618(6) 0.2716(5) 0.08974(14) 0.1038(15) Uani 1 1 d . . . O2 O 0.2588(6) 0.1161(6) 0.13962(12) 0.1036(17) Uani 1 1 d . . . H2 H 0.343(12) 0.210(14) 0.1290(16) 0.155 Uiso 1 1 d R . . O3 O -0.1108(4) -0.0781(5) 0.05267(9) 0.0753(11) Uani 1 1 d . . . O4 O -0.4327(5) -0.4064(5) 0.03104(9) 0.0730(10) Uani 1 1 d . . . O5 O -0.2439(5) -0.4570(5) 0.05560(9) 0.0733(11) Uani 1 1 d . . . O6 O -0.6712(6) -0.3954(10) 0.13091(13) 0.134(2) Uani 1 1 d . . . O7 O -0.9010(5) -0.5409(6) 0.10119(10) 0.0902(13) Uani 1 1 d . . . N N -0.1945(4) -0.2146(5) 0.09862(10) 0.0555(10) Uani 1 1 d . . . C1 C 0.0892(6) 0.0329(6) 0.09374(13) 0.0586(13) Uani 1 1 d . . . C2 C 0.1138(7) 0.0107(7) 0.12503(15) 0.0712(16) Uani 1 1 d . . . C3 C -0.0128(7) -0.1229(8) 0.14183(15) 0.0747(16) Uani 1 1 d . . . H3 H 0.008 -0.137 0.1624 0.09 Uiso 1 1 calc R . . C4 C -0.1657(7) -0.2337(7) 0.12920(13) 0.0637(14) Uani 1 1 d . . . C5 C -0.0739(6) -0.0833(6) 0.07948(14) 0.0588(13) Uani 1 1 d . . . C6 C 0.2267(7) 0.1707(7) 0.07656(15) 0.0745(17) Uani 1 1 d . . . C7 C 0.2120(9) 0.1946(9) 0.04264(19) 0.102(2) Uani 1 1 d . . . H7A H 0.1118 0.204 0.0389 0.153 Uiso 1 1 calc R . . H7B H 0.2027 0.0979 0.0315 0.153 Uiso 1 1 calc R . . H7C H 0.3122 0.2975 0.0358 0.153 Uiso 1 1 calc R . . C8 C -0.3021(8) -0.3804(9) 0.14739(16) 0.0901(18) Uani 1 1 d . . . H8A H -0.3256 -0.4869 0.138 0.135 Uiso 1 1 calc R . . H8B H -0.4048 -0.3728 0.1475 0.135 Uiso 1 1 calc R . . H8C H -0.2633 -0.3757 0.1683 0.135 Uiso 1 1 calc R . . C9 C -0.3642(6) -0.3203(6) 0.08386(12) 0.0579(13) Uani 1 1 d . . . H9 H -0.433 -0.417 0.0978 0.069 Uiso 1 1 calc R . . C10 C -0.4574(7) -0.2183(7) 0.08055(18) 0.0783(17) Uani 1 1 d . . . H10A H -0.4107 -0.1431 0.0627 0.094 Uiso 1 1 calc R . . H10B H -0.433 -0.1462 0.0987 0.094 Uiso 1 1 calc R . . C11 C -0.6522(7) -0.3265(8) 0.07673(17) 0.0787(17) Uani 1 1 d . . . H11 H -0.6781 -0.4091 0.0599 0.094 Uiso 1 1 calc R . . C12 C -0.7366(8) -0.4211(9) 0.10541(17) 0.0826(18) Uani 1 1 d . . . C13 C -0.7237(10) -0.2075(11) 0.0682(3) 0.144(4) Uani 1 1 d . . . H13A H -0.6721 -0.1484 0.0492 0.216 Uiso 1 1 calc R . . H13B H -0.6975 -0.1253 0.0845 0.216 Uiso 1 1 calc R . . H13C H -0.8459 -0.2748 0.0656 0.216 Uiso 1 1 calc R . . C14 C -0.9981(11) -0.6263(13) 0.12894(18) 0.118(3) Uani 1 1 d . . . H14A H -0.9925 -0.5422 0.1437 0.142 Uiso 1 1 calc R . . H14B H -0.9509 -0.6909 0.1387 0.142 Uiso 1 1 calc R . . C15 C -1.1764(10) -0.7419(12) 0.1197(3) 0.135(3) Uani 1 1 d . . . H15A H -1.2205 -0.6774 0.1094 0.203 Uiso 1 1 calc R . . H15B H -1.2444 -0.7964 0.1378 0.203 Uiso 1 1 calc R . . H15C H -1.1811 -0.8278 0.1059 0.203 Uiso 1 1 calc R . . C16 C -0.3494(6) -0.3939(6) 0.05352(13) 0.0612(13) Uani 1 1 d . . . C17 C -0.2315(12) -0.5395(12) 0.0276(2) 0.113(3) Uani 1 1 d . . . H17A H -0.3462 -0.6187 0.0202 0.136 Uiso 1 1 calc R . . H17B H -0.173 -0.453 0.0118 0.136 Uiso 1 1 calc R . . C18 C -0.147(2) -0.625(3) 0.0322(3) 0.267(12) Uani 1 1 d . . . H18A H -0.0397 -0.5514 0.0423 0.401 Uiso 1 1 calc R . . H18B H -0.1257 -0.6612 0.0125 0.401 Uiso 1 1 calc R . . H18C H -0.2149 -0.7238 0.0449 0.401 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 0.075(3) 0.076(2) 0.113(4) 0.002(3) -0.015(3) 0.002(2) O2 0.080(3) 0.094(3) 0.096(4) -0.013(3) -0.039(3) 0.013(2) O3 0.069(2) 0.074(2) 0.050(3) 0.0073(19) -0.005(2) 0.0113(18) O4 0.071(2) 0.070(2) 0.065(3) -0.005(2) -0.011(2) 0.0255(18) O5 0.073(2) 0.082(2) 0.073(3) -0.024(2) -0.012(2) 0.046(2) O6 0.085(3) 0.234(7) 0.075(4) -0.041(4) -0.004(3) 0.073(4) O7 0.065(2) 0.111(3) 0.081(3) -0.005(3) 0.001(2) 0.034(2) N 0.052(2) 0.052(2) 0.055(3) -0.003(2) 0.003(2) 0.0198(19) C1 0.057(3) 0.050(3) 0.056(4) -0.005(2) -0.002(3) 0.017(3) C2 0.065(3) 0.065(3) 0.076(5) -0.009(3) -0.012(3) 0.027(3) C3 0.071(4) 0.081(4) 0.058(4) 0.003(3) -0.002(3) 0.027(3) C4 0.072(4) 0.064(3) 0.051(4) 0.007(3) 0.005(3) 0.032(3) C5 0.058(3) 0.050(3) 0.060(4) -0.005(3) 0.002(3) 0.021(2) C6 0.058(3) 0.054(3) 0.087(5) -0.004(3) -0.008(3) 0.010(3) C7 0.080(4) 0.081(4) 0.093(5) 0.008(4) 0.001(4) 0.001(3) C8 0.082(4) 0.110(5) 0.065(4) 0.020(4) 0.007(3) 0.039(4) C9 0.051(3) 0.051(3) 0.058(3) -0.006(2) 0.000(2) 0.015(2) C10 0.064(3) 0.067(3) 0.106(5) -0.015(3) -0.008(3) 0.035(3) C11 0.068(3) 0.083(4) 0.094(5) -0.020(4) -0.010(3) 0.044(3) C12 0.072(4) 0.118(5) 0.067(5) -0.030(4) -0.005(4) 0.054(4) C13 0.085(4) 0.119(6) 0.245(13) -0.002(7) -0.029(7) 0.065(4) C14 0.114(6) 0.165(7) 0.081(5) 0.012(6) 0.024(5) 0.074(6) C15 0.083(5) 0.134(7) 0.150(9) -0.006(6) 0.025(5) 0.025(5) C16 0.053(3) 0.055(3) 0.058(4) -0.002(2) -0.001(3) 0.014(2) C17 0.125(6) 0.132(6) 0.113(7) -0.046(5) -0.005(5) 0.087(5) C18 0.38(2) 0.41(3) 0.202(14) -0.209(17) -0.170(16) 0.34(2) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 C6 1.233(7) . ? O2 C2 1.327(7) . ? O3 C5 1.211(6) . ? O4 C16 1.196(6) . ? O5 C16 1.330(6) . ? O5 C17 1.449(8) . ? O6 C12 1.213(8) . ? O7 C12 1.337(8) . ? O7 C14 1.455(9) . ? N C4 1.371(7) . ? N C5 1.404(6) . ? N C9 1.479(6) . ? C1 C2 1.398(8) . ? C1 C6 1.442(8) . ? C1 C5 1.445(7) . ? C2 C3 1.377(9) . ? C3 C4 1.346(8) . ? C4 C8 1.498(8) . ? C6 C7 1.494(10) . ? C9 C16 1.502(7) . ? C9 C10 1.528(8) . ? C10 C11 1.529(8) . ? C11 C12 1.478(10) . ? C11 C13 1.544(10) . ? C14 C15 1.464(12) . ? C17 C18 1.339(14) . ? 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 C16 O5 C17 114.6(5) . . ? C12 O7 C14 116.3(6) . . ? C4 N C5 123.8(4) . . ? C4 N C9 122.2(4) . . ? C5 N C9 113.7(4) . . ? C2 C1 C6 119.3(5) . . ? C2 C1 C5 118.9(5) . . ? C6 C1 C5 121.8(5) . . ? O2 C2 C3 117.5(6) . . ? O2 C2 C1 121.7(6) . . ? C3 C2 C1 120.8(5) . . ? C4 C3 C2 121.7(6) . . ? C3 C4 N 118.9(5) . . ? C3 C4 C8 121.6(5) . . ? N C4 C8 119.4(5) . . ? O3 C5 N 118.9(4) . . ? O3 C5 C1 125.3(5) . . ? N C5 C1 115.8(5) . . ? O1 C6 C1 120.1(6) . . ? O1 C6 C7 118.1(5) . . ? C1 C6 C7 121.8(5) . . ? N C9 C16 111.6(4) . . ? N C9 C10 110.7(4) . . ? C16 C9 C10 112.3(5) . . ? C9 C10 C11 115.2(4) . . ? C12 C11 C10 111.8(5) . . ? C12 C11 C13 109.0(7) . . ? C10 C11 C13 109.0(5) . . ? O6 C12 O7 120.8(7) . . ? O6 C12 C11 126.0(6) . . ? O7 C12 C11 113.1(6) . . ? O7 C14 C15 107.8(7) . . ? O4 C16 O5 124.2(5) . . ? O4 C16 C9 124.0(5) . . ? O5 C16 C9 111.6(5) . . ? C18 C17 O5 112.6(8) . . ? 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 C6 C1 C2 O2 1.9(8) . . . . ? C5 C1 C2 O2 -178.1(5) . . . . ? C6 C1 C2 C3 -177.8(6) . . . . ? C5 C1 C2 C3 2.2(8) . . . . ? O2 C2 C3 C4 178.3(6) . . . . ? C1 C2 C3 C4 -2.0(9) . . . . ? C2 C3 C4 N 1.3(9) . . . . ? C2 C3 C4 C8 179.1(6) . . . . ? C5 N C4 C3 -1.1(8) . . . . ? C9 N C4 C3 -174.0(5) . . . . ? C5 N C4 C8 -178.9(5) . . . . ? C9 N C4 C8 8.2(7) . . . . ? C4 N C5 O3 179.4(5) . . . . ? C9 N C5 O3 -7.2(7) . . . . ? C4 N C5 C1 1.4(7) . . . . ? C9 N C5 C1 174.8(4) . . . . ? C2 C1 C5 O3 -179.7(5) . . . . ? C6 C1 C5 O3 0.3(8) . . . . ? C2 C1 C5 N -1.9(7) . . . . ? C6 C1 C5 N 178.2(5) . . . . ? C2 C1 C6 O1 -2.8(9) . . . . ? C5 C1 C6 O1 177.1(5) . . . . ? C2 C1 C6 C7 176.3(6) . . . . ? C5 C1 C6 C7 -3.7(9) . . . . ? C4 N C9 C16 -131.6(5) . . . . ? C5 N C9 C16 54.8(5) . . . . ? C4 N C9 C10 102.5(6) . . . . ? C5 N C9 C10 -71.1(6) . . . . ? N C9 C10 C11 -159.1(5) . . . . ? C16 C9 C10 C11 75.4(7) . . . . ? C9 C10 C11 C12 68.8(7) . . . . ? C9 C10 C11 C13 -170.6(8) . . . . ? C14 O7 C12 O6 5.0(9) . . . . ? C14 O7 C12 C11 -173.4(6) . . . . ? C10 C11 C12 O6 13.8(9) . . . . ? C13 C11 C12 O6 -106.9(8) . . . . ? C10 C11 C12 O7 -168.0(5) . . . . ? C13 C11 C12 O7 71.4(7) . . . . ? C12 O7 C14 C15 175.7(7) . . . . ? C17 O5 C16 O4 2.0(8) . . . . ? C17 O5 C16 C9 176.5(6) . . . . ? N C9 C16 O4 -141.1(5) . . . . ? C10 C9 C16 O4 -16.1(7) . . . . ? N C9 C16 O5 44.4(5) . . . . ? C10 C9 C16 O5 169.4(4) . . . . ? C16 O5 C17 C18 -169.8(12) . . . . ? #===END