# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_cambridge 0177 #TrackingRef 'malik.cif' # 1. SUBMISSION DETAILS _publ_contact_author ; Prof. Dr. F.P.J.T. Rutjes Synthetic Organic Chemistry Institute for Molecules and Materials Radboud University Nijmegen Heyendaalseweg 135 6525 AJ Nijmegen The Netherlands ; _publ_contact_author_phone '031 024 3653202' _publ_contact_author_fax '031 024 3653393' _publ_contact_author_email f.rutjes@science.ru.nl _publ_requested_coeditor_name ? _publ_contact_letter ; ; #============================================================================== # 3. AUTHOR LIST loop_ _publ_author_address ; Synthetic Organic Chemistry Institute for Molecules and Materials Radboud University Nijmegen Heyendaalseweg 135 6525 AJ Nijmegen The Netherlands ; ; Synthetic Organic Chemistry Institute for Molecules and Materials Radboud University Nijmegen Heyendaalseweg 135 6525 AJ Nijmegen The Netherlands ; ; Solid State Chemistry Department Institute for Molecules and Materials Radboud University Nijmegen Heyendaalseweg 135 6525 AJ Nijmegen The Netherlands ; #============================================================================== # 4. TEXT _publ_section_title ; Crystal and Molecular Structure of MALIK1, MALIK2, MALIK3 and MALIK4 ; _publ_section_abstract ; ; _publ_section_references ; Duisenberg, A.J.M. (1998). Reflections on area detectors, PhD Thesis, Utrecht University, Utrecht, The Netherlands. International Tables for X-ray Crystallography (1974). Vol. IV, Birmingham, England: Kynoch Press. Nonius B.V. (1999). COLLECT, data collection software. Delft, The Netherlands. Sheldrick, G.M. (1996). SADABS. Program for Emperical Absorption Correction. University of G\"ottingen, Germany. Sheldrick, G.M. (1990). SHELXS. Acta Crystallogr. A46, 467-473. Sheldrick, G. M. (1997). SHELXL-97, Program for the refinement of crystal structures. University of G\"ottingen, Germany. Spek, A. L. (2003). PLATON. A Multipurpose Crystallographic Tool. Utrecht University, Utrecht, The Netherlands. ; _publ_section_figure_captions ; ; _publ_section_acknowledgements ; ; _publ_contact_author_name 'Prof. Dr. F.P.J.T. Rutjes' _publ_author_name B.Zwanenburg #============================================================================== data_MALIK1 _database_code_depnum_ccdc_archive 'CCDC 775138' #TrackingRef 'malik.cif' _audit_creation_method 'SHELXL, adapted and expanded' _audit_creation_date 2006-07-27 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C11 H10 O3' _chemical_formula_weight 190.19 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 'P 21/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 8.3372(4) _cell_length_b 10.9310(7) _cell_length_c 9.7141(3) _cell_angle_alpha 90.00 _cell_angle_beta 94.165(3) _cell_angle_gamma 90.00 _cell_volume 882.95(8) _cell_formula_units_Z 4 _cell_measurement_temperature 208(2) _cell_measurement_reflns_used 176 _cell_measurement_theta_min 2.450 _cell_measurement_theta_max 27.520 _exptl_crystal_description 'regular thick platelet' _exptl_crystal_colour 'translucent colourless' _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.05 #_exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.431 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 400 _exptl_absorpt_coefficient_mu 0.104 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS multiscan (Sheldrick, 1996)' _exptl_absorpt_correction_T_min 0.6879 _exptl_absorpt_correction_T_max 0.7456 _exptl_special_details ; ? ; _diffrn_ambient_temperature 208(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 'Nonius KappaCCD' _diffrn_measurement_method 'area detector \f and \w scan' _diffrn_detector_area_resol_mean 18.4 _diffrn_standards_number 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0.000 _diffrn_reflns_number 20709 _diffrn_reflns_av_R_equivalents 0.0310 _diffrn_reflns_av_sigmaI/netI 0.0173 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.45 _diffrn_reflns_theta_max 27.52 _reflns_number_total 2028 _reflns_number_gt 1729 _reflns_number_observed 1729 _reflns_threshold_expression >2sigma(I) _reflns_observed_criterion >2sigma(I) _computing_data_collection ; Nonius "Collect" program suite (Nonius, 1999) ; _computing_cell_refinement ? _computing_data_reduction ; Nonius "EvalCCD" program suite (Duisenberg, 1998) ; _computing_structure_solution ; ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; PLATON (Spek, 2003) ; _computing_publication_material ? _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 ; w=1/[\s^2^(Fo^2^)+(0.0416P)^2^+0.3201P] 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 none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2028 _refine_ls_number_parameters 128 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0537 _refine_ls_R_factor_gt 0.0429 _refine_ls_R_factor_obs 0.0429 _refine_ls_wR_factor_ref 0.1012 _refine_ls_wR_factor_all 0.1012 _refine_ls_wR_factor_gt 0.0959 _refine_ls_wR_factor_obs 0.0959 _refine_ls_goodness_of_fit_ref 1.098 _refine_ls_goodness_of_fit_all 1.098 _refine_ls_restrained_S_all 1.098 _refine_ls_shift/su_max 0.000 _refine_ls_shift/esd_max 0.000 _refine_ls_shift/su_mean 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_adp_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.33011(12) 0.12171(9) 0.08954(10) 0.0303(2) Uani 1 d . . . C2 C 0.48729(17) 0.14018(13) 0.07666(14) 0.0282(3) Uani 1 d . . . C3 C 0.51201(17) 0.23260(14) -0.03347(14) 0.0294(3) Uani 1 d . . . H3A H 0.5375 0.1927 -0.1196 0.035 Uiso 1 calc R . . H3B H 0.5989 0.2894 -0.0044 0.035 Uiso 1 calc R . . C4 C 0.35188(17) 0.29818(14) -0.05082(13) 0.0283(3) Uani 1 d . . . H4 H 0.3264 0.3219 -0.1483 0.034 Uiso 1 calc R . . C5 C 0.33311(16) 0.40804(13) 0.04631(14) 0.0265(3) Uani 1 d . . . H5 H 0.3381 0.4863 -0.0044 0.032 Uiso 1 calc R . . C6 C 0.16905(16) 0.38896(13) 0.09830(13) 0.0268(3) Uani 1 d . . . C7 C 0.07813(18) 0.47115(15) 0.16815(15) 0.0338(3) Uani 1 d . . . H7 H 0.1149 0.5514 0.1855 0.041 Uiso 1 calc R . . C8 C -0.06794(18) 0.43273(16) 0.21188(16) 0.0383(4) Uani 1 d . . . H8 H -0.1304 0.4871 0.2605 0.046 Uiso 1 calc R . . C9 C -0.12297(18) 0.31523(17) 0.18480(17) 0.0400(4) Uani 1 d . . . H9 H -0.2221 0.2905 0.2158 0.048 Uiso 1 calc R . . C10 C -0.03395(18) 0.23367(16) 0.11266(16) 0.0365(4) Uani 1 d . . . H10 H -0.0727 0.1545 0.0922 0.044 Uiso 1 calc R . . C11 C 0.11379(16) 0.27140(14) 0.07116(14) 0.0282(3) Uani 1 d . . . C12 C 0.23307(17) 0.20199(14) -0.00551(14) 0.0297(3) Uani 1 d . . . H12 H 0.1814 0.1564 -0.0849 0.036 Uiso 1 calc R . . O13 O 0.58714(13) 0.08487(10) 0.14735(12) 0.0399(3) Uani 1 d . . . O14 O 0.45589(11) 0.40201(10) 0.15645(10) 0.0310(2) Uani 1 d . . . H14 H 0.4449 0.4597 0.2105 0.046 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 O1 0.0332(5) 0.0257(5) 0.0327(5) 0.0009(4) 0.0072(4) -0.0026(4) C2 0.0335(7) 0.0252(7) 0.0264(7) -0.0046(6) 0.0055(6) -0.0005(6) C3 0.0324(7) 0.0319(7) 0.0247(7) -0.0009(6) 0.0073(5) -0.0015(6) C4 0.0312(7) 0.0348(8) 0.0189(6) 0.0030(6) 0.0020(5) -0.0027(6) C5 0.0278(7) 0.0250(7) 0.0267(7) 0.0060(5) 0.0009(5) -0.0018(5) C6 0.0261(6) 0.0316(7) 0.0222(6) 0.0053(6) -0.0019(5) 0.0012(6) C7 0.0328(8) 0.0348(8) 0.0330(7) 0.0017(6) -0.0025(6) 0.0055(6) C8 0.0304(8) 0.0509(10) 0.0336(8) 0.0016(7) 0.0015(6) 0.0121(7) C9 0.0242(7) 0.0578(11) 0.0380(8) 0.0067(8) 0.0026(6) 0.0015(7) C10 0.0287(7) 0.0411(9) 0.0392(8) 0.0033(7) -0.0007(6) -0.0063(6) C11 0.0262(7) 0.0335(8) 0.0241(6) 0.0031(6) -0.0023(5) -0.0019(6) C12 0.0316(7) 0.0331(8) 0.0239(6) -0.0032(6) -0.0015(5) -0.0047(6) O13 0.0398(6) 0.0363(6) 0.0433(6) 0.0091(5) 0.0022(5) 0.0059(5) O14 0.0297(5) 0.0327(6) 0.0298(5) -0.0054(4) -0.0028(4) 0.0003(4) _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 1.3407(17) . Y O1 C12 1.4727(17) . Y C2 O13 1.2029(17) . Y C2 C3 1.497(2) . Y C3 C4 1.514(2) . Y C4 C12 1.531(2) . Y C4 C5 1.542(2) . Y C5 O14 1.4275(16) . Y C5 C6 1.5066(19) . Y C6 C11 1.384(2) . Y C6 C7 1.385(2) . Y C7 C8 1.384(2) . Y C8 C9 1.383(3) . Y C9 C10 1.383(2) . Y C10 C11 1.3863(19) . Y C11 C12 1.492(2) . Y 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 C12 110.36(10) . . Y O13 C2 O1 120.77(13) . . Y O13 C2 C3 128.45(13) . . Y O1 C2 C3 110.77(12) . . Y C2 C3 C4 103.48(11) . . Y C3 C4 C12 103.09(12) . . Y C3 C4 C5 115.37(11) . . Y C12 C4 C5 105.21(11) . . Y O14 C5 C6 111.18(11) . . Y O14 C5 C4 108.87(11) . . Y C6 C5 C4 103.43(11) . . Y C11 C6 C7 120.62(13) . . Y C11 C6 C5 111.25(12) . . Y C7 C6 C5 128.11(14) . . Y C8 C7 C6 118.61(15) . . Y C9 C8 C7 120.71(15) . . Y C8 C9 C10 120.83(14) . . Y C9 C10 C11 118.46(16) . . Y C6 C11 C10 120.75(14) . . Y C6 C11 C12 110.02(12) . . Y C10 C11 C12 129.22(14) . . Y O1 C12 C11 110.22(11) . . Y O1 C12 C4 104.60(11) . . Y C11 C12 C4 105.24(12) . . Y loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O14 H14 O13 0.83 1.98 2.8029(15) 174.3 2_655 _diffrn_measured_fraction_theta_max 0.950 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.945 _refine_diff_density_max 0.231 _refine_diff_density_min -0.197 _refine_diff_density_rms 0.039 _publ_section_experimental ; Crystal colour: translucent colourless, crystal shape: regular thick platelet. Least-squares refinement using calculated weights: w=1/[\s^2^(Fo^2^)+(0.0416P)^2^+0.3201P] where P=(Fo^2^+2Fc^2^)/3 ; #============================================================================== data_MALIK2 _database_code_depnum_ccdc_archive 'CCDC 775139' #TrackingRef 'malik.cif' _audit_creation_method 'SHELXL, adapted and expanded' _audit_creation_date 2006-07-27 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C17 H14 O6' _chemical_formula_weight 314.28 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 triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.8264(3) _cell_length_b 8.0831(3) _cell_length_c 12.8838(11) _cell_angle_alpha 91.219(4) _cell_angle_beta 96.917(6) _cell_angle_gamma 94.850(4) _cell_volume 702.85(7) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 112 _cell_measurement_theta_min 1.590 _cell_measurement_theta_max 27.520 _exptl_crystal_description 'rather regular rod' _exptl_crystal_colour 'translucent colourless' _exptl_crystal_size_max 0.31 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.05 #_exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.485 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 328 _exptl_absorpt_coefficient_mu 0.114 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS multiscan (Sheldrick, 1996)' _exptl_absorpt_correction_T_min 0.7155 _exptl_absorpt_correction_T_max 0.7456 _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 'Nonius KappaCCD' _diffrn_measurement_method 'area detector \f and \w scan' _diffrn_detector_area_resol_mean 18.4 _diffrn_standards_number 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0.000 _diffrn_reflns_number 17511 _diffrn_reflns_av_R_equivalents 0.0366 _diffrn_reflns_av_sigmaI/netI 0.0339 _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 -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.59 _diffrn_reflns_theta_max 27.52 _reflns_number_total 3233 _reflns_number_gt 2491 _reflns_number_observed 2491 _reflns_threshold_expression >2sigma(I) _reflns_observed_criterion >2sigma(I) _computing_data_collection ; Nonius "Collect" program suite (Nonius, 1999) ; _computing_cell_refinement ? _computing_data_reduction ; Nonius "EvalCCD" program suite (Duisenberg, 1998) ; _computing_structure_solution ; ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; PLATON (Spek, 2003) ; _computing_publication_material ? _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 ; w=1/[\s^2^(Fo^2^)+(0.1523P)^2^+2.8792P] 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 none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3233 _refine_ls_number_parameters 210 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1218 _refine_ls_R_factor_gt 0.1001 _refine_ls_R_factor_obs 0.1001 _refine_ls_wR_factor_ref 0.3089 _refine_ls_wR_factor_all 0.3089 _refine_ls_wR_factor_gt 0.2932 _refine_ls_wR_factor_obs 0.2932 _refine_ls_goodness_of_fit_ref 1.076 _refine_ls_goodness_of_fit_all 1.076 _refine_ls_restrained_S_all 1.076 _refine_ls_shift/su_max 0.000 _refine_ls_shift/esd_max 0.000 _refine_ls_shift/su_mean 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_adp_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.1391(6) 0.1905(5) 0.7541(3) 0.0214(8) Uani 1 d . . . C2 C 0.0832(6) 0.3573(5) 0.7201(3) 0.0205(8) Uani 1 d . . . H2 H 0.0740 0.3640 0.6438 0.025 Uiso 1 calc R . . C3 C -0.1072(6) 0.4144(5) 0.7608(3) 0.0231(9) Uani 1 d . . . H3 H -0.1797 0.3220 0.7918 0.028 Uiso 1 calc R . . C4 C -0.0299(6) 0.5480(5) 0.8423(3) 0.0206(8) Uani 1 d . . . C5 C -0.1388(7) 0.6348(6) 0.9042(3) 0.0266(9) Uani 1 d . . . H5 H -0.2749 0.6097 0.9011 0.032 Uiso 1 calc R . . C6 C -0.0423(8) 0.7603(6) 0.9712(3) 0.0303(10) Uani 1 d . . . H6 H -0.1145 0.8225 1.0120 0.036 Uiso 1 calc R . . C7 C 0.1607(8) 0.7933(5) 0.9775(4) 0.0301(10) Uani 1 d . . . H7 H 0.2238 0.8763 1.0240 0.036 Uiso 1 calc R . . C8 C 0.2714(7) 0.7062(5) 0.9167(4) 0.0273(9) Uani 1 d . . . H8 H 0.4080 0.7297 0.9212 0.033 Uiso 1 calc R . . C9 C 0.1739(6) 0.5817(5) 0.8479(3) 0.0208(8) Uani 1 d . . . C10 C 0.2608(6) 0.4726(5) 0.7736(3) 0.0225(9) Uani 1 d . . . H10 H 0.3246 0.5386 0.7220 0.027 Uiso 1 calc R . . O11 O 0.3991(4) 0.3680(4) 0.8294(3) 0.0281(7) Uani 1 d . . . C12 C 0.3339(6) 0.2061(5) 0.8170(3) 0.0233(9) Uani 1 d . . . O13 O -0.2319(5) 0.4860(4) 0.6809(3) 0.0311(8) Uani 1 d . . . H13 H -0.3262 0.4191 0.6600 0.047 Uiso 1 calc R . . O14 O 0.4299(5) 0.0989(4) 0.8541(3) 0.0346(8) Uani 1 d . . . C15 C 0.0366(6) 0.0443(5) 0.7369(3) 0.0232(9) Uani 1 d . . . H15 H 0.0912 -0.0504 0.7627 0.028 Uiso 1 calc R . . O16 O -0.1471(5) 0.0302(3) 0.6821(3) 0.0274(7) Uani 1 d . . . C17 C -0.2382(6) -0.1329(5) 0.6624(3) 0.0225(9) Uani 1 d . . . H17 H -0.1740 -0.2102 0.7104 0.027 Uiso 1 calc R . . O18 O -0.2228(4) -0.1806(4) 0.5555(2) 0.0276(7) Uani 1 d . . . C19 C -0.4073(6) -0.2333(5) 0.5096(3) 0.0250(9) Uani 1 d . . . C20 C -0.5540(6) -0.2066(5) 0.5811(3) 0.0222(8) Uani 1 d . . . C21 C -0.4533(6) -0.1419(5) 0.6700(3) 0.0233(9) Uani 1 d . . . H21 H -0.5100 -0.1075 0.7280 0.028 Uiso 1 calc R . . O22 O -0.4329(5) -0.2919(5) 0.4218(3) 0.0418(10) Uani 1 d . . . C23 C -0.7687(7) -0.2500(7) 0.5521(4) 0.0331(11) Uani 1 d . . . H23A H -0.8361 -0.2392 0.6128 0.050 Uiso 1 calc R . . H23B H -0.7907 -0.3624 0.5250 0.050 Uiso 1 calc R . . H23C H -0.8188 -0.1765 0.4997 0.050 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 0.022(2) 0.023(2) 0.0189(18) -0.0030(15) 0.0022(15) 0.0029(15) C2 0.0212(19) 0.0185(18) 0.0212(19) -0.0022(14) 0.0020(15) -0.0009(15) C3 0.021(2) 0.0205(19) 0.027(2) 0.0023(16) 0.0000(16) 0.0008(15) C4 0.024(2) 0.0185(18) 0.0197(18) 0.0024(14) 0.0023(15) 0.0039(15) C5 0.024(2) 0.031(2) 0.026(2) 0.0031(17) 0.0041(17) 0.0038(17) C6 0.042(3) 0.030(2) 0.022(2) -0.0017(17) 0.0080(18) 0.0105(19) C7 0.041(3) 0.023(2) 0.025(2) -0.0038(16) -0.0025(19) -0.0008(18) C8 0.026(2) 0.024(2) 0.031(2) -0.0008(17) -0.0020(17) 0.0000(16) C9 0.025(2) 0.0171(18) 0.0213(19) 0.0009(15) 0.0038(15) 0.0039(15) C10 0.0208(19) 0.0184(18) 0.028(2) 0.0007(15) 0.0052(16) -0.0014(15) O11 0.0192(15) 0.0222(15) 0.0406(18) -0.0053(13) -0.0029(13) -0.0004(11) C12 0.021(2) 0.023(2) 0.026(2) -0.0064(16) 0.0029(16) 0.0033(16) O13 0.0273(17) 0.0248(16) 0.0369(18) -0.0036(13) -0.0139(13) 0.0036(13) O14 0.0299(18) 0.0286(17) 0.043(2) -0.0062(14) -0.0067(15) 0.0076(14) C15 0.024(2) 0.0202(19) 0.024(2) -0.0025(15) -0.0031(16) 0.0042(15) O16 0.0265(16) 0.0156(14) 0.0361(17) 0.0022(12) -0.0103(13) -0.0024(11) C17 0.026(2) 0.0157(18) 0.024(2) -0.0023(15) -0.0017(16) -0.0012(15) O18 0.0185(15) 0.0330(17) 0.0296(16) -0.0063(13) 0.0022(12) -0.0040(12) C19 0.0184(19) 0.027(2) 0.028(2) -0.0025(17) 0.0014(16) -0.0038(16) C20 0.020(2) 0.0208(19) 0.026(2) 0.0007(15) 0.0041(16) 0.0007(15) C21 0.024(2) 0.0217(19) 0.024(2) -0.0022(15) 0.0037(16) -0.0004(15) O22 0.0310(19) 0.061(2) 0.0309(18) -0.0195(17) 0.0069(15) -0.0087(17) C23 0.019(2) 0.047(3) 0.032(2) 0.001(2) 0.0013(17) -0.0031(19) _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 C15 1.322(6) . Y C1 C12 1.466(6) . Y C1 C2 1.492(6) . Y C2 C10 1.547(6) . Y C2 C3 1.560(6) . Y C3 O13 1.420(5) . Y C3 C4 1.507(6) . Y C4 C5 1.374(6) . Y C4 C9 1.388(6) . Y C5 C6 1.386(6) . Y C6 C7 1.381(7) . Y C7 C8 1.376(7) . Y C8 C9 1.395(6) . Y C9 C10 1.495(6) . Y C10 O11 1.456(5) . Y O11 C12 1.346(5) . Y C12 O14 1.203(5) . Y C15 O16 1.357(5) . Y O16 C17 1.414(5) . Y C17 O18 1.441(5) . Y C17 C21 1.479(6) . Y O18 C19 1.355(5) . Y C19 O22 1.204(5) . Y C19 C20 1.466(6) . Y C20 C21 1.334(6) . Y C20 C23 1.479(6) . Y 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 C15 C1 C12 120.8(4) . . Y C15 C1 C2 128.9(4) . . Y C12 C1 C2 110.2(3) . . Y C1 C2 C10 101.7(3) . . Y C1 C2 C3 115.4(3) . . Y C10 C2 C3 107.2(3) . . Y O13 C3 C4 108.2(3) . . Y O13 C3 C2 111.9(4) . . Y C4 C3 C2 104.0(3) . . Y C5 C4 C9 121.1(4) . . Y C5 C4 C3 127.1(4) . . Y C9 C4 C3 111.8(4) . . Y C4 C5 C6 118.8(4) . . Y C7 C6 C5 120.2(4) . . Y C8 C7 C6 121.4(4) . . Y C7 C8 C9 118.4(4) . . Y C4 C9 C8 120.0(4) . . Y C4 C9 C10 111.7(4) . . Y C8 C9 C10 128.2(4) . . Y O11 C10 C9 111.1(3) . . Y O11 C10 C2 107.5(3) . . Y C9 C10 C2 104.9(3) . . Y C12 O11 C10 111.5(3) . . Y O14 C12 O11 121.9(4) . . Y O14 C12 C1 129.1(4) . . Y O11 C12 C1 109.0(3) . . Y C1 C15 O16 121.0(4) . . Y C15 O16 C17 116.3(3) . . Y O16 C17 O18 108.4(3) . . Y O16 C17 C21 111.9(3) . . Y O18 C17 C21 105.0(3) . . Y C19 O18 C17 107.6(3) . . Y O22 C19 O18 120.8(4) . . Y O22 C19 C20 128.9(4) . . Y O18 C19 C20 110.3(4) . . Y C21 C20 C19 106.6(4) . . Y C21 C20 C23 130.7(4) . . Y C19 C20 C23 122.7(4) . . Y C20 C21 C17 109.9(4) . . Y loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O13 H13 O22 0.82 2.03 2.833(5) 165.8 2_456 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.904 _refine_diff_density_min -0.354 _refine_diff_density_rms 0.143 _publ_section_experimental ; Crystal colour: translucent colourless, crystal shape: rather regular rod. Least-squares refinement using calculated weights: w=1/[\s^2^(Fo^2^)+(0.1523P)^2^+2.8792P] where P=(Fo^2^+2Fc^2^)/3 The crystal structure determination was hampered by the poor crystal quality. Only a few crystals were more or less suitable for data collection and all of them had some minor fragments attached to them which could not be removed. This resulted in a poor final R-value of 0.1001 and rather high residual densities in the final difference fourier map. However, there is no doubt about the molecular geometry. ; #============================================================================== data_MALIK3 _database_code_depnum_ccdc_archive 'CCDC 775140' #TrackingRef 'malik.cif' _audit_creation_method 'SHELXL, adapted and expanded' _audit_creation_date 2006-07-27 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C17 H14 O6' _chemical_formula_weight 314.28 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 'P c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x, -y, z+1/2' _cell_length_a 8.1223(3) _cell_length_b 7.0400(5) _cell_length_c 13.0388(3) _cell_angle_alpha 90.00 _cell_angle_beta 107.502(4) _cell_angle_gamma 90.00 _cell_volume 711.06(6) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 235 _cell_measurement_theta_min 2.630 _cell_measurement_theta_max 27.490 _exptl_crystal_description 'rough fragment' _exptl_crystal_colour 'translucent colourless' _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.17 #_exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.468 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 328 _exptl_absorpt_coefficient_mu 0.112 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS multiscan (Sheldrick, 1996)' _exptl_absorpt_correction_T_min 0.7117 _exptl_absorpt_correction_T_max 0.7456 _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 'Nonius KappaCCD' _diffrn_measurement_method 'area detector \f and \w scan' _diffrn_detector_area_resol_mean 18.4 _diffrn_standards_number 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0.000 _diffrn_reflns_number 18049 _diffrn_reflns_av_R_equivalents 0.0276 _diffrn_reflns_av_sigmaI/netI 0.0214 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.63 _diffrn_reflns_theta_max 27.49 _reflns_number_total 3244 _reflns_number_gt 2946 _reflns_number_observed 2946 _reflns_threshold_expression >2sigma(I) _reflns_observed_criterion >2sigma(I) _computing_data_collection ; Nonius "Collect" program suite (Nonius, 1999) ; _computing_cell_refinement ? _computing_data_reduction ; Nonius "EvalCCD" program suite (Duisenberg, 1998) ; _computing_structure_solution ; ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; PLATON (Spek, 2003) ; _computing_publication_material ? _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 ; w=1/[\s^2^(Fo^2^)+(0.0406P)^2^+0.1046P] 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 none _refine_ls_extinction_coef ? _refine_ls_abs_structure_Flack 0.4(7) _refine_ls_number_reflns 3244 _refine_ls_number_parameters 210 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0397 _refine_ls_R_factor_gt 0.0341 _refine_ls_R_factor_obs 0.0341 _refine_ls_wR_factor_ref 0.0797 _refine_ls_wR_factor_all 0.0797 _refine_ls_wR_factor_gt 0.0770 _refine_ls_wR_factor_obs 0.0770 _refine_ls_goodness_of_fit_ref 1.083 _refine_ls_goodness_of_fit_all 1.083 _refine_ls_restrained_S_all 1.082 _refine_ls_shift/su_max 0.000 _refine_ls_shift/esd_max 0.000 _refine_ls_shift/su_mean 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_adp_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.32407(19) 0.3826(2) -0.04289(12) 0.0237(3) Uani 1 d . . . C2 C 0.34151(19) 0.5914(2) -0.01995(12) 0.0226(3) Uani 1 d . . . H2 H 0.2323 0.6581 -0.0523 0.027 Uiso 1 calc R . . C3 C 0.41883(18) 0.6421(2) 0.09975(12) 0.0201(3) Uani 1 d . . . H3 H 0.3929 0.5442 0.1461 0.024 Uiso 1 calc R . . C4 C 0.61059(19) 0.6539(2) 0.11448(13) 0.0218(3) Uani 1 d . . . C5 C 0.7454(2) 0.6572(2) 0.20943(14) 0.0274(4) Uani 1 d . . . H5 H 0.7242 0.6530 0.2756 0.033 Uiso 1 calc R . . C6 C 0.9128(2) 0.6670(2) 0.20329(17) 0.0346(4) Uani 1 d . . . H6 H 1.0051 0.6686 0.2662 0.042 Uiso 1 calc R . . C7 C 0.9444(2) 0.6744(2) 0.10504(17) 0.0361(4) Uani 1 d . . . H7 H 1.0577 0.6796 0.1027 0.043 Uiso 1 calc R . . C8 C 0.8105(2) 0.6742(3) 0.01039(16) 0.0338(4) Uani 1 d . . . H8 H 0.8318 0.6814 -0.0557 0.041 Uiso 1 calc R . . C9 C 0.6434(2) 0.6629(2) 0.01637(13) 0.0247(3) Uani 1 d . . . C10 C 0.4790(2) 0.6475(2) -0.07464(13) 0.0279(4) Uani 1 d . . . H10 H 0.4500 0.7668 -0.1147 0.033 Uiso 1 calc R . . O11 O 0.49190(16) 0.48922(18) -0.14409(10) 0.0353(3) Uani 1 d . . . C12 C 0.4206(2) 0.3312(3) -0.11698(13) 0.0302(4) Uani 1 d . . . O13 O 0.35004(15) 0.82210(16) 0.11636(10) 0.0273(3) Uani 1 d . . . H13 H 0.3768 0.8447 0.1810 0.041 Uiso 1 calc R . . O14 O 0.43838(19) 0.17855(19) -0.15431(11) 0.0411(3) Uani 1 d . . . C15 C 0.2335(2) 0.2492(2) -0.01204(12) 0.0247(3) Uani 1 d . . . H15 H 0.2425 0.1238 -0.0320 0.030 Uiso 1 calc R . . O16 O 0.12908(16) 0.29171(17) 0.04745(11) 0.0324(3) Uani 1 d . . . C17 C 0.0521(2) 0.1357(2) 0.08434(14) 0.0293(4) Uani 1 d . . . H17 H 0.0708 0.0180 0.0492 0.035 Uiso 1 calc R . . O18 O 0.12893(14) 0.12274(18) 0.19791(10) 0.0332(3) Uani 1 d . . . C19 C 0.0014(2) 0.1283(2) 0.24621(14) 0.0278(4) Uani 1 d . . . C20 C -0.1660(2) 0.1542(2) 0.16275(14) 0.0253(3) Uani 1 d . . . C21 C -0.1350(2) 0.1641(2) 0.06974(14) 0.0290(4) Uani 1 d . . . H21 H -0.2182 0.1859 0.0041 0.035 Uiso 1 calc R . . O22 O 0.03161(17) 0.11240(19) 0.34165(10) 0.0402(3) Uani 1 d . . . C23 C -0.3297(2) 0.1603(3) 0.19278(16) 0.0347(4) Uani 1 d . . . H23A H -0.4264 0.1437 0.1295 0.052 Uiso 1 calc R . . H23B H -0.3389 0.2807 0.2252 0.052 Uiso 1 calc R . . H23C H -0.3289 0.0603 0.2430 0.052 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 0.0203(7) 0.0310(8) 0.0173(7) -0.0017(6) 0.0019(6) -0.0015(6) C2 0.0186(7) 0.0285(8) 0.0188(7) 0.0025(6) 0.0029(6) 0.0018(6) C3 0.0166(7) 0.0240(7) 0.0207(7) 0.0001(6) 0.0072(6) 0.0001(6) C4 0.0173(7) 0.0205(8) 0.0273(8) -0.0013(6) 0.0066(6) -0.0001(6) C5 0.0241(8) 0.0256(8) 0.0301(9) -0.0029(6) 0.0047(6) 0.0007(6) C6 0.0191(7) 0.0270(9) 0.0501(11) -0.0060(8) -0.0013(8) -0.0014(7) C7 0.0208(8) 0.0250(9) 0.0662(13) -0.0066(8) 0.0190(8) -0.0031(7) C8 0.0343(10) 0.0282(9) 0.0491(11) -0.0036(7) 0.0282(8) -0.0043(7) C9 0.0250(8) 0.0218(8) 0.0308(8) -0.0004(7) 0.0139(7) -0.0030(6) C10 0.0333(9) 0.0305(9) 0.0225(8) 0.0023(7) 0.0124(7) -0.0004(7) O11 0.0473(7) 0.0414(7) 0.0237(6) -0.0053(5) 0.0208(5) -0.0072(6) C12 0.0310(9) 0.0403(10) 0.0183(7) -0.0056(7) 0.0060(6) -0.0026(7) O13 0.0232(5) 0.0307(6) 0.0291(6) -0.0058(5) 0.0097(5) 0.0035(5) O14 0.0556(9) 0.0399(7) 0.0341(7) -0.0128(6) 0.0233(6) -0.0051(6) C15 0.0227(7) 0.0282(8) 0.0219(7) -0.0040(6) 0.0045(6) -0.0001(6) O16 0.0336(6) 0.0240(6) 0.0467(8) -0.0014(5) 0.0230(6) -0.0036(5) C17 0.0311(9) 0.0249(8) 0.0344(9) -0.0001(6) 0.0138(8) -0.0036(7) O18 0.0215(6) 0.0399(7) 0.0363(7) 0.0039(5) 0.0059(5) 0.0005(5) C19 0.0266(8) 0.0234(8) 0.0324(9) -0.0003(7) 0.0075(7) -0.0016(7) C20 0.0224(8) 0.0201(8) 0.0318(9) 0.0008(7) 0.0055(6) -0.0020(6) C21 0.0252(8) 0.0280(9) 0.0306(9) 0.0029(7) 0.0038(7) -0.0029(7) O22 0.0421(7) 0.0463(8) 0.0287(7) -0.0012(6) 0.0052(6) -0.0048(6) C23 0.0289(9) 0.0310(9) 0.0472(11) 0.0050(8) 0.0160(8) 0.0012(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 C15 1.328(2) . Y C1 C12 1.461(2) . Y C1 C2 1.498(2) . Y C2 C3 1.539(2) . Y C2 C10 1.546(2) . Y C3 O13 1.4278(19) . Y C3 C4 1.513(2) . Y C4 C9 1.384(2) . Y C4 C5 1.384(2) . Y C5 C6 1.388(2) . Y C6 C7 1.381(3) . Y C7 C8 1.378(3) . Y C8 C9 1.386(2) . Y C9 C10 1.500(2) . Y C10 O11 1.459(2) . Y O11 C12 1.349(2) . Y C12 O14 1.206(2) . Y C15 O16 1.3440(19) . Y O16 C17 1.418(2) . Y C17 O18 1.426(2) . Y C17 C21 1.487(3) . Y O18 C19 1.365(2) . Y C19 O22 1.199(2) . Y C19 C20 1.476(2) . Y C20 C21 1.313(2) . Y C20 C23 1.495(2) . Y 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 C15 C1 C12 118.79(15) . . Y C15 C1 C2 131.39(15) . . Y C12 C1 C2 109.73(14) . . Y C1 C2 C3 114.53(12) . . Y C1 C2 C10 101.34(13) . . Y C3 C2 C10 106.11(12) . . Y O13 C3 C4 111.51(12) . . Y O13 C3 C2 107.50(12) . . Y C4 C3 C2 103.42(12) . . Y C9 C4 C5 120.37(14) . . Y C9 C4 C3 111.22(13) . . Y C5 C4 C3 128.41(15) . . Y C4 C5 C6 118.31(16) . . Y C7 C6 C5 120.93(16) . . Y C8 C7 C6 120.93(16) . . Y C7 C8 C9 118.20(17) . . Y C4 C9 C8 121.25(15) . . Y C4 C9 C10 110.80(13) . . Y C8 C9 C10 127.86(16) . . Y O11 C10 C9 109.47(14) . . Y O11 C10 C2 106.72(13) . . Y C9 C10 C2 104.36(13) . . Y C12 O11 C10 110.51(12) . . Y O14 C12 O11 121.06(16) . . Y O14 C12 C1 129.83(17) . . Y O11 C12 C1 109.09(14) . . Y C1 C15 O16 121.39(15) . . Y C15 O16 C17 116.28(14) . . Y O16 C17 O18 107.56(14) . . Y O16 C17 C21 112.97(14) . . Y O18 C17 C21 104.65(14) . . Y C19 O18 C17 108.74(13) . . Y O22 C19 O18 121.98(15) . . Y O22 C19 C20 129.22(17) . . Y O18 C19 C20 108.80(14) . . Y C21 C20 C19 107.31(15) . . Y C21 C20 C23 132.32(16) . . Y C19 C20 C23 120.36(16) . . Y C20 C21 C17 110.31(15) . . Y loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O13 H13 O14 0.82 2.06 2.8575(18) 164.2 2_565 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.207 _refine_diff_density_min -0.180 _refine_diff_density_rms 0.036 _publ_section_experimental ; Crystal colour: translucent colourless, crystal shape: rough fragment. Least-squares refinement using calculated weights: w=1/[\s^2^(Fo^2^)+(0.0406P)^2^+0.1046P] where P=(Fo^2^+2Fc^2^)/3 ; #============================================================================== data_MALIK4 _database_code_depnum_ccdc_archive 'CCDC 775141' #TrackingRef 'malik.cif' _audit_creation_method 'SHELXL, adapted and expanded' _audit_creation_date 2006-07-27 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C17 H14 O6' _chemical_formula_weight 314.28 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 'P 21/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 6.6845(9) _cell_length_b 7.9964(10) _cell_length_c 26.937(3) _cell_angle_alpha 90.00 _cell_angle_beta 94.935(8) _cell_angle_gamma 90.00 _cell_volume 1434.5(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 29 _cell_measurement_theta_min 1.520 _cell_measurement_theta_max 25.010 _exptl_crystal_description 'rather regular thin needle' _exptl_crystal_colour 'translucent colourless' _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.03 _exptl_crystal_size_min 0.02 #_exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.455 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 656 _exptl_absorpt_coefficient_mu 0.111 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS multiscan (Sheldrick, 1996)' _exptl_absorpt_correction_T_min 0.6487 _exptl_absorpt_correction_T_max 0.7452 _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 'Nonius KappaCCD' _diffrn_measurement_method 'area detector \f and \w scan' _diffrn_detector_area_resol_mean 18.4 _diffrn_standards_number 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0.000 _diffrn_reflns_number 29442 _diffrn_reflns_av_R_equivalents 0.1277 _diffrn_reflns_av_sigmaI/netI 0.0698 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -32 _diffrn_reflns_limit_l_max 32 _diffrn_reflns_theta_min 1.52 _diffrn_reflns_theta_max 25.01 _reflns_number_total 2536 _reflns_number_gt 1646 _reflns_number_observed 1646 _reflns_threshold_expression >2sigma(I) _reflns_observed_criterion >2sigma(I) _computing_data_collection ; Nonius "Collect" program suite (Nonius, 1999) ; _computing_cell_refinement ? _computing_data_reduction ; Nonius "EvalCCD" program suite (Duisenberg, 1998) ; _computing_structure_solution ; ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; PLATON (Spek, 2003) ; _computing_publication_material ? _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 ; w=1/[\s^2^(Fo^2^)+(0.0842P)^2^+0.1052P] 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 none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2536 _refine_ls_number_parameters 210 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1350 _refine_ls_R_factor_gt 0.0793 _refine_ls_R_factor_obs 0.0793 _refine_ls_wR_factor_ref 0.1847 _refine_ls_wR_factor_all 0.1847 _refine_ls_wR_factor_gt 0.1549 _refine_ls_wR_factor_obs 0.1549 _refine_ls_goodness_of_fit_ref 1.185 _refine_ls_goodness_of_fit_all 1.185 _refine_ls_restrained_S_all 1.185 _refine_ls_shift/su_max 0.000 _refine_ls_shift/esd_max 0.000 _refine_ls_shift/su_mean 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_adp_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.5501(5) 0.3405(4) 0.17543(14) 0.0267(9) Uani 1 d . . . C2 C 0.6604(5) 0.2613(4) 0.21983(13) 0.0250(9) Uani 1 d . . . H2 H 0.7012 0.1475 0.2117 0.030 Uiso 1 calc R . . C3 C 0.8446(5) 0.3607(4) 0.24486(13) 0.0247(9) Uani 1 d . . . H3 H 0.9645 0.2897 0.2471 0.030 Uiso 1 calc R . . C4 C 0.7845(5) 0.3980(5) 0.29620(13) 0.0264(9) Uani 1 d . . . C5 C 0.8954(6) 0.4801(5) 0.33454(15) 0.0405(11) Uani 1 d . . . H5 H 1.0220 0.5222 0.3297 0.049 Uiso 1 calc R . . C6 C 0.8174(7) 0.4990(6) 0.37954(16) 0.0495(12) Uani 1 d . . . H6 H 0.8925 0.5523 0.4056 0.059 Uiso 1 calc R . . C7 C 0.6281(7) 0.4395(6) 0.38657(16) 0.0509(12) Uani 1 d . . . H7 H 0.5765 0.4545 0.4172 0.061 Uiso 1 calc R . . C8 C 0.5150(6) 0.3587(5) 0.34902(15) 0.0398(11) Uani 1 d . . . H8 H 0.3879 0.3179 0.3540 0.048 Uiso 1 calc R . . C9 C 0.5947(5) 0.3392(4) 0.30356(14) 0.0268(9) Uani 1 d . . . C10 C 0.5003(5) 0.2559(5) 0.25775(13) 0.0273(9) Uani 1 d . . . H10 H 0.4614 0.1406 0.2647 0.033 Uiso 1 calc R . . O11 O 0.3285(3) 0.3529(3) 0.23579(9) 0.0297(7) Uani 1 d . . . C12 C 0.3526(5) 0.3935(5) 0.18802(14) 0.0290(9) Uani 1 d . . . O13 O 0.8845(3) 0.5133(3) 0.22046(9) 0.0282(7) Uani 1 d . . . H13 H 0.9807 0.5007 0.2039 0.042 Uiso 1 calc R . . O14 O 0.2188(4) 0.4645(3) 0.16300(10) 0.0357(7) Uani 1 d . . . C15 C 0.6162(5) 0.3730(5) 0.13155(14) 0.0311(10) Uani 1 d . . . H15 H 0.5354 0.4300 0.1073 0.037 Uiso 1 calc R . . O16 O 0.8029(3) 0.3224(3) 0.12223(9) 0.0360(7) Uani 1 d . . . C17 C 0.8934(6) 0.4008(6) 0.08317(14) 0.0393(11) Uani 1 d . . . H17 H 1.0351 0.3680 0.0850 0.047 Uiso 1 calc R . . O18 O 0.7972(4) 0.3469(4) 0.03603(10) 0.0493(9) Uani 1 d . . . C19 C 0.7464(6) 0.4867(8) 0.00855(17) 0.0563(14) Uani 1 d . . . C20 C 0.7962(6) 0.6353(7) 0.03816(18) 0.0524(14) Uani 1 d . . . C21 C 0.8810(6) 0.5858(6) 0.08176(16) 0.0412(11) Uani 1 d . . . H21 H 0.9262 0.6566 0.1077 0.049 Uiso 1 calc R . . O22 O 0.6750(5) 0.4747(6) -0.03397(11) 0.0831(14) Uani 1 d . . . C23 C 0.7543(9) 0.8071(8) 0.0184(2) 0.091(2) Uani 1 d . . . H23A H 0.7809 0.8871 0.0448 0.136 Uiso 1 calc R . . H23B H 0.6161 0.8149 0.0056 0.136 Uiso 1 calc R . . H23C H 0.8390 0.8300 -0.0078 0.136 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 0.025(2) 0.028(2) 0.027(2) -0.0013(18) 0.0019(17) -0.0022(16) C2 0.0192(18) 0.022(2) 0.034(2) -0.0024(18) 0.0048(16) 0.0026(15) C3 0.0221(19) 0.027(2) 0.025(2) 0.0048(17) 0.0020(16) 0.0013(15) C4 0.026(2) 0.028(2) 0.025(2) 0.0039(18) 0.0042(17) -0.0009(16) C5 0.040(2) 0.050(3) 0.031(2) 0.005(2) 0.000(2) -0.012(2) C6 0.058(3) 0.058(3) 0.032(3) -0.004(2) -0.001(2) -0.013(2) C7 0.072(3) 0.057(3) 0.025(2) 0.000(2) 0.012(2) -0.006(3) C8 0.040(2) 0.047(3) 0.033(3) 0.003(2) 0.010(2) -0.0031(19) C9 0.029(2) 0.025(2) 0.026(2) 0.0061(17) 0.0043(17) 0.0020(16) C10 0.0202(18) 0.029(2) 0.033(2) 0.0055(18) 0.0030(17) 0.0039(16) O11 0.0214(13) 0.0386(16) 0.0298(16) 0.0035(12) 0.0047(11) 0.0016(11) C12 0.026(2) 0.033(2) 0.028(2) -0.0050(19) 0.0035(18) -0.0072(18) O13 0.0266(14) 0.0303(15) 0.0289(15) 0.0042(12) 0.0089(11) -0.0026(11) O14 0.0238(14) 0.0499(18) 0.0325(16) 0.0047(14) -0.0023(12) 0.0047(13) C15 0.023(2) 0.041(3) 0.029(2) -0.0030(19) 0.0019(17) 0.0012(17) O16 0.0259(14) 0.0561(19) 0.0269(16) 0.0039(14) 0.0069(12) 0.0101(12) C17 0.029(2) 0.068(3) 0.021(2) -0.007(2) 0.0041(18) 0.004(2) O18 0.0383(17) 0.087(3) 0.0227(16) -0.0098(16) 0.0018(13) 0.0082(15) C19 0.030(2) 0.112(5) 0.028(3) 0.013(3) 0.011(2) 0.024(3) C20 0.037(3) 0.080(4) 0.044(3) 0.022(3) 0.021(2) 0.018(2) C21 0.032(2) 0.058(3) 0.035(3) 0.007(2) 0.0077(19) 0.003(2) O22 0.045(2) 0.182(4) 0.0216(19) 0.009(2) 0.0020(15) 0.030(2) C23 0.088(4) 0.110(5) 0.079(4) 0.057(4) 0.039(3) 0.039(4) _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 C15 1.323(5) . Y C1 C12 1.454(5) . Y C1 C2 1.491(5) . Y C2 C10 1.542(5) . Y C2 C3 1.568(5) . Y C3 O13 1.422(4) . Y C3 C4 1.503(5) . Y C4 C9 1.383(5) . Y C4 C5 1.384(5) . Y C5 C6 1.369(6) . Y C6 C7 1.380(6) . Y C7 C8 1.372(6) . Y C8 C9 1.385(5) . Y C9 C10 1.494(5) . Y C10 O11 1.467(4) . Y O11 C12 1.350(4) . Y C12 O14 1.213(4) . Y C15 O16 1.356(4) . Y O16 C17 1.406(5) . Y C17 O18 1.439(4) . Y C17 C21 1.482(6) . Y O18 C19 1.367(6) . Y C19 O22 1.206(5) . Y C19 C20 1.454(7) . Y C20 C21 1.320(6) . Y C20 C23 1.490(7) . Y 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 C15 C1 C12 122.1(3) . . Y C15 C1 C2 128.3(3) . . Y C12 C1 C2 109.5(3) . . Y C1 C2 C10 102.7(3) . . Y C1 C2 C3 116.4(3) . . Y C10 C2 C3 107.1(3) . . Y O13 C3 C4 109.3(3) . . Y O13 C3 C2 114.1(3) . . Y C4 C3 C2 103.5(3) . . Y C9 C4 C5 119.6(3) . . Y C9 C4 C3 112.7(3) . . Y C5 C4 C3 127.8(3) . . Y C6 C5 C4 119.5(4) . . Y C5 C6 C7 120.5(4) . . Y C8 C7 C6 121.0(4) . . Y C7 C8 C9 118.4(4) . . Y C4 C9 C8 121.1(4) . . Y C4 C9 C10 111.1(3) . . Y C8 C9 C10 127.8(3) . . Y O11 C10 C9 110.9(3) . . Y O11 C10 C2 106.4(3) . . Y C9 C10 C2 105.5(3) . . Y C12 O11 C10 111.0(3) . . Y O14 C12 O11 120.0(3) . . Y O14 C12 C1 130.3(4) . . Y O11 C12 C1 109.7(3) . . Y C1 C15 O16 119.4(3) . . Y C15 O16 C17 117.9(3) . . Y O16 C17 O18 109.8(3) . . Y O16 C17 C21 115.9(3) . . Y O18 C17 C21 104.9(3) . . Y C19 O18 C17 107.7(4) . . Y O22 C19 O18 120.6(5) . . Y O22 C19 C20 129.7(5) . . Y O18 C19 C20 109.7(4) . . Y C21 C20 C19 107.7(4) . . Y C21 C20 C23 130.3(6) . . Y C19 C20 C23 122.1(5) . . Y C20 C21 C17 109.9(4) . . Y loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O13 H13 O14 0.82 2.03 2.853(3) 178.9 1_655 _diffrn_measured_fraction_theta_max 0.928 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.928 _refine_diff_density_max 0.303 _refine_diff_density_min -0.336 _refine_diff_density_rms 0.095 _publ_section_experimental ; Crystal colour: translucent colourless, crystal shape: rather regular thin needle. Least-squares refinement using calculated weights: w=1/[\s^2^(Fo^2^)+(0.0842P)^2^+0.1052P] where P=(Fo^2^+2Fc^2^)/3 The crystals were extremely thin and fragile. This resulted in a weak diffraction power and no useful data could be collected above 25\% \q. The resulting internal R-value was rather poor, Rint = 0.128. The resulting crystal structure, however, is quite acceptable and certainly reliable. From the thermal displacement parameters for the atoms O16 - C23 is it clear that this part of the molecule is rotating rather strongly, or it has a rather large degree of freedom, around the bond C15-O16. Because of the non-discrete nature of this movement it was impossible to parameterize this movement into one or more discrete positions. ; #===END