Supplementary Material for Organic & Biomolecular Chemistry This journal is © The Royal Society of Chemistry 2005 data_global _journal_coden_Cambridge 177 loop_ _publ_author_name 'J. Mann' 'David Cousin' 'Mark Niewenhuyzen' 'van den Berg,Hendrik' _publ_contact_author_name J.Mann _publ_contact_author_address ; School of Chemistry Queen's University Belfast Belfast Northern Ireland BT9 5AG UNITED KINGDOM ; _publ_contact_author_email J.MANN@QUB.AC.UK _publ_requested_journal 'Organic & Biomolecular Chemistry' _publ_section_title ; A new approach to combretastatin D2 ; data_d1m _database_code_depnum_ccdc_archive 'CCDC 283472' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H18 O4' _chemical_formula_weight 310.33 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 Orthorhombic _symmetry_space_group_name_H-M Pbca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 13.47(5) _cell_length_b 10.86(4) _cell_length_c 21.40(10) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3132(22) _cell_formula_units_Z 8 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.316 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1312 _exptl_absorpt_coefficient_mu 0.092 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 153(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5614 _diffrn_reflns_av_R_equivalents 0.3716 _diffrn_reflns_av_sigmaI/netI 0.4081 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 1.90 _diffrn_reflns_theta_max 22.50 _reflns_number_total 2022 _reflns_number_gt 498 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1056P)^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 geom _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.051(5) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2022 _refine_ls_number_parameters 209 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.3103 _refine_ls_R_factor_gt 0.1041 _refine_ls_wR_factor_ref 0.2935 _refine_ls_wR_factor_gt 0.2006 _refine_ls_goodness_of_fit_ref 0.843 _refine_ls_restrained_S_all 0.846 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.1310(7) 0.3966(8) 0.6807(4) 0.064(3) Uani 1 1 d . . . C2 C 0.1350(11) 0.3311(14) 0.6235(6) 0.059(4) Uani 1 1 d . . . C3 C 0.1517(9) 0.3990(12) 0.5684(6) 0.060(4) Uani 1 1 d . . . H3A H 0.1486 0.4864 0.5679 0.072 Uiso 1 1 calc R . . C4 C 0.1731(10) 0.3304(13) 0.5139(6) 0.059(4) Uani 1 1 d . . . H4A H 0.1864 0.3727 0.4760 0.071 Uiso 1 1 calc R . . C5 C 0.1751(10) 0.2046(13) 0.5146(6) 0.056(4) Uani 1 1 d . . . C6 C 0.1486(9) 0.1383(11) 0.5687(5) 0.050(4) Uani 1 1 d . . . H6A H 0.1456 0.0509 0.5687 0.060 Uiso 1 1 calc R . . C7 C 0.1262(9) 0.2084(14) 0.6235(6) 0.059(4) Uani 1 1 d . . . H7A H 0.1049 0.1673 0.6603 0.071 Uiso 1 1 calc R . . C8 C 0.2175(11) 0.1360(13) 0.4612(6) 0.064(4) Uani 1 1 d . . . H8A H 0.1762 0.0787 0.4401 0.076 Uiso 1 1 calc R . . C9 C 0.3112(13) 0.1503(14) 0.4408(6) 0.078(5) Uani 1 1 d . . . H9A H 0.3315 0.1037 0.4055 0.094 Uiso 1 1 calc R . . C10 C 0.3871(10) 0.2361(12) 0.4705(5) 0.064(4) Uani 1 1 d U . . H10A H 0.4494 0.2364 0.4460 0.076 Uiso 1 1 calc R . . H10B H 0.3610 0.3212 0.4724 0.076 Uiso 1 1 calc R . . O11 O 0.4051(6) 0.1886(8) 0.5337(4) 0.058(3) Uani 1 1 d . . . C12 C 0.4531(12) 0.2748(16) 0.5715(7) 0.070(5) Uani 1 1 d . . . O12 O 0.4691(8) 0.3780(9) 0.5555(4) 0.072(3) Uani 1 1 d . . . C13 C 0.4769(10) 0.2137(11) 0.6338(5) 0.058(4) Uani 1 1 d . . . H13A H 0.5368 0.1617 0.6293 0.070 Uiso 1 1 calc R . . H13B H 0.4210 0.1601 0.6465 0.070 Uiso 1 1 calc R . . C14 C 0.4952(9) 0.3127(12) 0.6849(5) 0.061(4) Uani 1 1 d . . . H14A H 0.5284 0.2724 0.7208 0.074 Uiso 1 1 calc R . . H14B H 0.5419 0.3746 0.6679 0.074 Uiso 1 1 calc R . . C15 C 0.4039(10) 0.3805(13) 0.7094(6) 0.055(4) Uani 1 1 d . . . C16 C 0.4083(10) 0.4685(13) 0.7551(6) 0.061(4) Uani 1 1 d . . . H16A H 0.4716 0.4875 0.7722 0.073 Uiso 1 1 calc R . . C17 C 0.3270(11) 0.5317(13) 0.7782(6) 0.062(4) Uani 1 1 d . . . H17A H 0.3338 0.5895 0.8112 0.074 Uiso 1 1 calc R . . C18 C 0.2365(11) 0.5082(14) 0.7518(7) 0.057(4) Uani 1 1 d . . . C19 C 0.2273(10) 0.4170(14) 0.7050(6) 0.054(4) Uani 1 1 d . . . C20 C 0.3116(12) 0.3576(13) 0.6842(6) 0.064(4) Uani 1 1 d . . . H20A H 0.3059 0.2991 0.6514 0.077 Uiso 1 1 calc R . . O21 O 0.1467(7) 0.5624(8) 0.7686(3) 0.064(3) Uani 1 1 d . . . C22 C 0.1504(10) 0.6495(12) 0.8195(5) 0.070(4) Uani 1 1 d . . . H22A H 0.0836 0.6819 0.8274 0.105 Uiso 1 1 calc R . . H22B H 0.1949 0.7175 0.8085 0.105 Uiso 1 1 calc R . . H22C H 0.1751 0.6084 0.8572 0.105 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 0.059(7) 0.089(8) 0.044(6) -0.017(5) 0.002(5) 0.000(6) C2 0.074(11) 0.059(11) 0.045(9) 0.001(8) 0.004(8) -0.007(9) C3 0.063(10) 0.061(10) 0.057(10) -0.010(8) 0.002(8) -0.010(8) C4 0.075(11) 0.057(10) 0.045(9) 0.000(8) -0.008(7) 0.009(9) C5 0.073(11) 0.051(10) 0.044(9) -0.006(8) 0.000(7) -0.016(9) C6 0.062(10) 0.044(8) 0.044(9) -0.007(8) -0.007(8) -0.006(8) C7 0.048(10) 0.079(12) 0.051(9) 0.015(9) 0.012(7) -0.002(9) C8 0.080(12) 0.072(11) 0.039(9) -0.006(8) -0.012(8) -0.002(10) C9 0.097(13) 0.095(13) 0.042(9) 0.000(8) -0.001(10) 0.005(11) C10 0.076(8) 0.079(8) 0.035(6) 0.020(6) -0.010(6) 0.005(7) O11 0.059(6) 0.074(7) 0.040(5) 0.006(5) 0.003(5) 0.003(6) C12 0.075(13) 0.086(13) 0.050(11) -0.002(11) 0.014(8) 0.015(12) O12 0.091(8) 0.075(7) 0.050(6) 0.002(6) -0.002(5) 0.006(7) C13 0.065(10) 0.059(10) 0.050(9) 0.007(8) -0.012(7) 0.011(8) C14 0.063(11) 0.078(11) 0.044(9) -0.007(8) -0.005(7) 0.018(9) C15 0.030(9) 0.086(12) 0.050(9) -0.006(8) -0.003(8) 0.012(9) C16 0.051(10) 0.093(12) 0.040(9) 0.005(9) -0.007(8) -0.008(10) C17 0.057(10) 0.088(12) 0.041(9) 0.010(8) -0.007(8) -0.003(10) C18 0.054(11) 0.068(11) 0.049(10) 0.022(9) 0.014(9) 0.005(9) C19 0.040(10) 0.083(12) 0.039(9) 0.006(8) 0.005(7) 0.005(9) C20 0.075(12) 0.074(11) 0.044(9) -0.002(8) 0.011(9) -0.001(10) O21 0.071(7) 0.086(7) 0.035(5) -0.013(5) -0.002(5) -0.011(6) C22 0.082(11) 0.082(11) 0.046(8) -0.028(8) 0.001(8) 0.004(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 C19 1.415(15) . ? O1 C2 1.416(14) . ? C2 C7 1.339(16) . ? C2 C3 1.409(16) . ? C3 C4 1.413(15) . ? C4 C5 1.367(16) . ? C5 C6 1.409(15) . ? C5 C8 1.479(17) . ? C6 C7 1.431(16) . ? C8 C9 1.345(17) . ? C9 C10 1.522(17) . ? C10 O11 1.468(13) . ? O11 C12 1.396(17) . ? C12 O12 1.192(16) . ? C12 C13 1.524(18) . ? C13 C14 1.554(15) . ? C14 C15 1.526(16) . ? C15 C16 1.369(16) . ? C15 C20 1.378(16) . ? C16 C17 1.384(16) . ? C17 C18 1.367(16) . ? C18 O21 1.393(14) . ? C18 C19 1.415(17) . ? C19 C20 1.380(16) . ? O21 C22 1.445(13) . ? 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 C19 O1 C2 111.2(11) . . ? C7 C2 C3 122.3(14) . . ? C7 C2 O1 119.8(13) . . ? C3 C2 O1 117.8(13) . . ? C2 C3 C4 116.6(13) . . ? C5 C4 C3 121.5(13) . . ? C4 C5 C6 121.0(13) . . ? C4 C5 C8 120.2(13) . . ? C6 C5 C8 118.4(13) . . ? C5 C6 C7 117.1(12) . . ? C2 C7 C6 120.7(13) . . ? C9 C8 C5 123.7(14) . . ? C8 C9 C10 124.4(14) . . ? O11 C10 C9 106.3(10) . . ? C12 O11 C10 112.0(11) . . ? O12 C12 O11 123.3(15) . . ? O12 C12 C13 128.5(16) . . ? O11 C12 C13 108.2(14) . . ? C12 C13 C14 110.4(12) . . ? C15 C14 C13 116.7(11) . . ? C16 C15 C20 116.4(14) . . ? C16 C15 C14 123.2(14) . . ? C20 C15 C14 120.3(13) . . ? C15 C16 C17 124.5(14) . . ? C18 C17 C16 117.8(14) . . ? C17 C18 O21 126.1(15) . . ? C17 C18 C19 120.1(14) . . ? O21 C18 C19 113.7(14) . . ? C20 C19 C18 118.9(14) . . ? C20 C19 O1 124.3(14) . . ? C18 C19 O1 116.8(13) . . ? C15 C20 C19 122.1(14) . . ? C18 O21 C22 116.2(11) . . ? _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 22.50 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 0.377 _refine_diff_density_min -0.342 _refine_diff_density_rms 0.102