# Electronic Supplementary Material (ESI) for RSC Advances # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_mnb74 #TrackingRef 'mnb74.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H10 O3' _chemical_formula_weight 214.21 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 7.3536(15) _cell_length_b 7.5164(15) _cell_length_c 9.6215(19) _cell_angle_alpha 74.24(3) _cell_angle_beta 78.39(3) _cell_angle_gamma 78.91(3) _cell_volume 495.97(17) _cell_formula_units_Z 2 _cell_measurement_temperature 170(2) _cell_measurement_reflns_used 5228 _cell_measurement_theta_min 6.7 _cell_measurement_theta_max 58.8 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.434 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 224 _exptl_absorpt_coefficient_mu 0.102 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.8331 _exptl_absorpt_correction_T_max 0.9478 _exptl_absorpt_process_details 'face indexed' _exptl_special_details ; ? ; _diffrn_ambient_temperature 170(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5228 _diffrn_reflns_av_R_equivalents 0.0483 _diffrn_reflns_av_sigmaI/netI 0.0520 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 3.34 _diffrn_reflns_theta_max 29.16 _reflns_number_total 2614 _reflns_number_gt 1703 _reflns_threshold_expression >2\s(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _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^ > 2\s(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^)+(0.0505P)^2^+0.2228P] 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_extinction_coef ? _refine_ls_number_reflns 2614 _refine_ls_number_parameters 174 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0995 _refine_ls_R_factor_gt 0.0558 _refine_ls_wR_factor_ref 0.1416 _refine_ls_wR_factor_gt 0.1184 _refine_ls_goodness_of_fit_ref 1.089 _refine_ls_restrained_S_all 1.089 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _iucr_refine_instructions_details ; TITL mnb74 in P-1 CELL 0.71073 7.3536 7.5164 9.6215 74.243 78.385 78.911 ZERR 2.00 0.0015 0.0015 0.0019 0.030 0.030 0.030 LATT 1 SFAC C H O UNIT 26 20 6 MERG 2 FMAP 2 PLAN -5 SIZE 0.08 0.16 0.36 ACTA 50.00 L.S. 24 TEMP -103.00 WGHT 0.050500 0.222800 FVAR 1.46780 C1 1 -0.410540 1.089218 0.195183 11.00000 0.03564 0.04360 = 0.04664 -0.01225 -0.01649 -0.00399 AFIX 137 H1A 2 -0.433850 1.013641 0.133861 11.00000 -1.50000 H1B 2 -0.405859 1.218128 0.137632 11.00000 -1.50000 H1C 2 -0.511859 1.087566 0.278888 11.00000 -1.50000 AFIX 0 C2 1 -0.226074 1.009737 0.249264 11.00000 0.02815 0.03348 = 0.03738 -0.01471 -0.01107 -0.00156 C3 1 -0.220177 0.882483 0.384714 11.00000 0.02553 0.03453 = 0.03551 -0.01363 -0.00596 -0.00437 C4 1 -0.047949 0.812110 0.431254 11.00000 0.02487 0.03005 = 0.03113 -0.01227 -0.00458 -0.00315 C5 1 0.017865 0.687347 0.559522 11.00000 0.02523 0.02928 = 0.02781 -0.01004 -0.00358 -0.00479 C6 1 -0.074593 0.581894 0.692065 11.00000 0.02797 0.02881 = 0.03042 -0.01026 -0.00454 -0.00374 C7 1 0.321640 0.378728 0.898092 11.00000 0.04003 0.04286 = 0.03449 -0.00332 -0.01072 -0.00325 C8 1 0.233347 0.486923 0.769231 11.00000 0.03035 0.03033 = 0.03072 -0.01039 -0.00601 -0.00348 C9 1 0.323407 0.579191 0.641442 11.00000 0.02547 0.03508 = 0.03285 -0.01067 -0.00732 -0.00372 C10 1 0.208496 0.680786 0.537971 11.00000 0.02736 0.03000 = 0.02593 -0.00796 -0.00366 -0.00628 C11 1 0.114449 0.870125 0.340727 11.00000 0.02334 0.03472 = 0.02932 -0.00953 -0.00766 -0.00322 C12 1 0.114038 0.995562 0.206900 11.00000 0.03105 0.04020 = 0.02975 -0.00613 -0.00605 -0.00635 C13 1 -0.058920 1.064464 0.163230 11.00000 0.03604 0.03810 = 0.03267 -0.01040 -0.01000 -0.00453 O1 3 -0.239120 0.565498 0.727022 11.00000 0.02667 0.04361 = 0.03964 -0.00864 0.00063 -0.00832 O2 3 0.043596 0.486858 0.794082 11.00000 0.02776 0.03489 = 0.03084 -0.00625 -0.00354 -0.00522 O3 3 0.272899 0.789319 0.405554 11.00000 0.02323 0.03840 = 0.02868 -0.00449 -0.00444 -0.00584 H12 2 0.232346 1.036227 0.143389 11.00000 0.03995 H3 2 -0.334453 0.843192 0.444142 11.00000 0.03383 H9 2 0.460093 0.571377 0.630670 11.00000 0.03743 H13 2 -0.070115 1.157597 0.064493 11.00000 0.04970 H7A 2 0.293607 0.245572 0.921606 11.00000 0.05806 H7B 2 0.461231 0.374001 0.879511 11.00000 0.04960 H7C 2 0.269661 0.437070 0.981584 11.00000 0.06643 HKLF 4 REM mnb74 in P-1 REM R1 = 0.0558 for 1703 Fo > 4sig(Fo) and 0.0995 for all 2614 data REM 174 parameters refined using 0 restraints END WGHT 0.0513 0.2220 REM Highest difference peak 0.224, deepest hole -0.259, 1-sigma level 0.053 Q1 1 0.1088 0.6791 0.5561 11.00000 0.05 0.22 Q2 1 -0.4840 0.9674 0.2295 11.00000 0.05 0.22 Q3 1 -0.3087 0.6936 0.5974 11.00000 0.05 0.22 Q4 1 0.0237 0.8547 0.3833 11.00000 0.05 0.21 Q5 1 -0.4457 1.2332 0.2202 11.00000 0.05 0.21 ; 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 C1 C -0.4105(3) 1.0892(3) 0.1952(3) 0.0405(5) Uani 1 1 d . . . H1A H -0.4339 1.0136 0.1339 0.061 Uiso 1 1 calc R . . H1B H -0.4059 1.2181 0.1376 0.061 Uiso 1 1 calc R . . H1C H -0.5119 1.0876 0.2789 0.061 Uiso 1 1 calc R . . C2 C -0.2261(3) 1.0097(3) 0.2493(2) 0.0313(5) Uani 1 1 d . . . C3 C -0.2202(3) 0.8825(3) 0.3847(2) 0.0307(4) Uani 1 1 d . . . C4 C -0.0479(3) 0.8121(3) 0.4313(2) 0.0278(4) Uani 1 1 d . . . C5 C 0.0179(3) 0.6873(3) 0.5595(2) 0.0268(4) Uani 1 1 d . . . C6 C -0.0746(3) 0.5819(3) 0.6921(2) 0.0285(4) Uani 1 1 d . . . C7 C 0.3216(4) 0.3787(4) 0.8981(3) 0.0400(5) Uani 1 1 d . . . C8 C 0.2333(3) 0.4869(3) 0.7692(2) 0.0298(4) Uani 1 1 d . . . C9 C 0.3234(3) 0.5792(3) 0.6414(2) 0.0303(4) Uani 1 1 d . . . C10 C 0.2085(3) 0.6808(3) 0.5380(2) 0.0273(4) Uani 1 1 d . . . C11 C 0.1144(3) 0.8701(3) 0.3407(2) 0.0284(4) Uani 1 1 d . . . C12 C 0.1140(3) 0.9956(3) 0.2069(2) 0.0338(5) Uani 1 1 d . . . C13 C -0.0589(3) 1.0645(3) 0.1632(2) 0.0347(5) Uani 1 1 d . . . O1 O -0.2391(2) 0.5655(2) 0.72702(17) 0.0373(4) Uani 1 1 d . . . O2 O 0.0436(2) 0.4869(2) 0.79408(15) 0.0316(3) Uani 1 1 d . . . O3 O 0.27290(19) 0.7893(2) 0.40555(15) 0.0306(3) Uani 1 1 d . . . H12 H 0.232(4) 1.036(4) 0.143(3) 0.040(7) Uiso 1 1 d . . . H3 H -0.334(3) 0.843(3) 0.444(3) 0.034(6) Uiso 1 1 d . . . H9 H 0.460(4) 0.571(3) 0.631(3) 0.037(6) Uiso 1 1 d . . . H13 H -0.070(4) 1.158(4) 0.064(3) 0.050(7) Uiso 1 1 d . . . H7A H 0.294(4) 0.246(4) 0.922(3) 0.058(8) Uiso 1 1 d . . . H7B H 0.461(4) 0.374(4) 0.880(3) 0.050(7) Uiso 1 1 d . . . H7C H 0.270(4) 0.437(4) 0.982(3) 0.066(9) Uiso 1 1 d . . . 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 0.0356(12) 0.0436(13) 0.0466(13) -0.0122(11) -0.0165(10) -0.0040(10) C2 0.0281(10) 0.0335(11) 0.0374(11) -0.0147(9) -0.0111(8) -0.0016(8) C3 0.0255(10) 0.0345(11) 0.0355(11) -0.0136(9) -0.0060(8) -0.0044(8) C4 0.0249(10) 0.0301(10) 0.0311(10) -0.0123(8) -0.0046(8) -0.0032(8) C5 0.0252(9) 0.0293(10) 0.0278(9) -0.0100(8) -0.0036(7) -0.0048(7) C6 0.0280(10) 0.0288(10) 0.0304(10) -0.0103(8) -0.0045(8) -0.0037(8) C7 0.0400(13) 0.0429(14) 0.0345(11) -0.0033(10) -0.0107(10) -0.0032(10) C8 0.0304(10) 0.0303(10) 0.0307(10) -0.0104(8) -0.0060(8) -0.0035(8) C9 0.0255(10) 0.0351(11) 0.0329(10) -0.0107(9) -0.0073(8) -0.0037(8) C10 0.0274(10) 0.0300(10) 0.0259(9) -0.0080(8) -0.0037(7) -0.0063(8) C11 0.0233(9) 0.0347(11) 0.0293(10) -0.0095(8) -0.0077(7) -0.0032(8) C12 0.0310(11) 0.0402(12) 0.0298(10) -0.0061(9) -0.0061(8) -0.0064(9) C13 0.0360(11) 0.0381(12) 0.0327(11) -0.0104(9) -0.0100(9) -0.0045(9) O1 0.0267(8) 0.0436(9) 0.0396(8) -0.0086(7) 0.0006(6) -0.0083(6) O2 0.0278(7) 0.0349(8) 0.0308(7) -0.0062(6) -0.0035(6) -0.0052(6) O3 0.0232(7) 0.0384(8) 0.0287(7) -0.0045(6) -0.0044(5) -0.0058(6) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 C2 1.507(3) . ? C2 C3 1.395(3) . ? C2 C13 1.402(3) . ? C3 C4 1.388(3) . ? C4 C11 1.396(3) . ? C4 C5 1.440(3) . ? C5 C10 1.368(3) . ? C5 C6 1.423(3) . ? C6 O1 1.210(2) . ? C6 O2 1.397(3) . ? C7 C8 1.481(3) . ? C8 C9 1.348(3) . ? C8 O2 1.367(2) . ? C9 C10 1.402(3) . ? C10 O3 1.362(2) . ? C11 C12 1.374(3) . ? C11 O3 1.389(2) . ? C12 C13 1.381(3) . ? 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 C3 C2 C13 119.6(2) . . ? C3 C2 C1 120.53(19) . . ? C13 C2 C1 119.9(2) . . ? C4 C3 C2 119.04(19) . . ? C3 C4 C11 119.02(19) . . ? C3 C4 C5 136.54(19) . . ? C11 C4 C5 104.42(17) . . ? C10 C5 C6 119.86(19) . . ? C10 C5 C4 106.99(17) . . ? C6 C5 C4 133.15(18) . . ? O1 C6 O2 116.95(19) . . ? O1 C6 C5 128.8(2) . . ? O2 C6 C5 114.28(17) . . ? C9 C8 O2 122.19(19) . . ? C9 C8 C7 125.7(2) . . ? O2 C8 C7 112.07(18) . . ? C8 C9 C10 115.46(19) . . ? O3 C10 C5 111.90(18) . . ? O3 C10 C9 123.91(18) . . ? C5 C10 C9 124.16(19) . . ? C12 C11 O3 125.11(18) . . ? C12 C11 C4 123.56(19) . . ? O3 C11 C4 111.30(17) . . ? C11 C12 C13 116.4(2) . . ? C12 C13 C2 122.4(2) . . ? C8 O2 C6 123.92(16) . . ? C10 O3 C11 105.39(15) . . ? _diffrn_measured_fraction_theta_max 0.980 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.224 _refine_diff_density_min -0.259 _refine_diff_density_rms 0.053 _database_code_depnum_ccdc_archive 'CCDC 932992' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_mnb69 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H14 O5' _chemical_formula_weight 310.29 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/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 9.4706(19) _cell_length_b 26.200(5) _cell_length_c 11.299(2) _cell_angle_alpha 90.00 _cell_angle_beta 95.64(3) _cell_angle_gamma 90.00 _cell_volume 2790.0(10) _cell_formula_units_Z 8 _cell_measurement_temperature 170(2) _cell_measurement_reflns_used 30990 _cell_measurement_theta_min 3.1 _cell_measurement_theta_max 58.7 _exptl_crystal_description platelet _exptl_crystal_colour yellow _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.477 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1296 _exptl_absorpt_coefficient_mu 0.108 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.8905 _exptl_absorpt_correction_T_max 0.9681 _exptl_absorpt_process_details 'face indexed' _exptl_special_details ; ? ; _diffrn_ambient_temperature 170(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 29840 _diffrn_reflns_av_R_equivalents 0.0746 _diffrn_reflns_av_sigmaI/netI 0.0611 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -35 _diffrn_reflns_limit_k_max 35 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.18 _diffrn_reflns_theta_max 29.26 _reflns_number_total 7494 _reflns_number_gt 3794 _reflns_threshold_expression >2\s(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _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^ > 2\s(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^)+(0.0701P)^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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7494 _refine_ls_number_parameters 419 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1175 _refine_ls_R_factor_gt 0.0498 _refine_ls_wR_factor_ref 0.1416 _refine_ls_wR_factor_gt 0.1135 _refine_ls_goodness_of_fit_ref 0.950 _refine_ls_restrained_S_all 0.950 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _iucr_refine_instructions_details ; TITL test in P2(1)/c CELL 0.71073 9.4706 26.1995 11.2990 90.000 95.644 90.000 ZERR 8.00 0.0019 0.0052 0.0023 0.000 0.030 0.000 LATT 1 SYMM - X, 1/2 + Y, 1/2 - Z SFAC C H O UNIT 144 112 40 MERG 2 FMAP 2 PLAN 20 SIZE 0.05 0.30 0.30 ACTA BOND L.S. 8 TEMP -103.00 WGHT 0.070100 FVAR 0.10531 MOLE 1 O1 3 -0.113715 0.642935 0.367749 11.00000 0.04911 0.01990 = 0.04382 -0.00019 0.02343 0.00294 O2 3 0.047145 0.620405 0.203704 11.00000 0.04348 0.02076 = 0.04036 0.00365 0.02096 0.00057 O3 3 0.160514 0.443518 0.142354 11.00000 0.06386 0.02753 = 0.05815 -0.00045 0.04111 -0.00119 O4 3 0.093949 0.365908 0.177611 11.00000 0.04793 0.02222 = 0.04934 -0.00333 0.02636 0.00034 O5 3 -0.199297 0.412559 0.397572 11.00000 0.04529 0.02176 = 0.04917 -0.00391 0.02609 -0.00252 C1 1 -0.209167 0.656892 0.452406 11.00000 0.04553 0.02789 = 0.04105 -0.00358 0.01871 0.00501 AFIX 137 H1A 2 -0.304737 0.644718 0.425265 11.00000 -1.50000 H1B 2 -0.210509 0.694123 0.460596 11.00000 -1.50000 H1C 2 -0.177812 0.641422 0.529502 11.00000 -1.50000 AFIX 0 C2 1 0.120930 0.609512 0.102723 11.00000 0.04714 0.03019 = 0.03902 0.00382 0.02332 0.00046 AFIX 137 H2A 2 0.210594 0.592306 0.128482 11.00000 -1.50000 H2B 2 0.140487 0.641442 0.062207 11.00000 -1.50000 H2C 2 0.062479 0.587291 0.047996 11.00000 -1.50000 AFIX 0 C3 1 -0.095574 0.592099 0.348680 11.00000 0.03340 0.01908 = 0.03212 -0.00027 0.00959 0.00241 C4 1 -0.005814 0.579694 0.261215 11.00000 0.03169 0.02038 = 0.02920 0.00340 0.00959 -0.00176 C5 1 0.023933 0.529541 0.237442 11.00000 0.02913 0.02461 = 0.02413 -0.00001 0.00994 0.00082 AFIX 43 H5 2 0.086533 0.521505 0.179392 11.00000 -1.20000 AFIX 0 C6 1 -0.038324 0.490193 0.299065 11.00000 0.02618 0.02156 = 0.02619 0.00047 0.00552 0.00053 C7 1 -0.016126 0.435463 0.276927 11.00000 0.02930 0.01961 = 0.02716 -0.00151 0.00635 -0.00011 C8 1 0.083432 0.417674 0.197065 11.00000 0.04192 0.02352 = 0.03529 -0.00114 0.01376 -0.00001 C9 1 0.010254 0.331257 0.228780 11.00000 0.03555 0.02460 = 0.03691 -0.00006 0.00852 0.00005 C10 1 0.029639 0.280520 0.200959 11.00000 0.05042 0.02665 = 0.05250 -0.00507 0.01748 0.00501 AFIX 43 H10 2 0.097918 0.270836 0.148956 11.00000 -1.20000 AFIX 0 C11 1 -0.052277 0.244309 0.250334 11.00000 0.06001 0.02160 = 0.06610 -0.00097 0.02035 0.00201 AFIX 43 H11 2 -0.040274 0.209221 0.232632 11.00000 -1.20000 AFIX 0 C12 1 -0.151784 0.258749 0.325451 11.00000 0.06731 0.02297 = 0.07607 0.00420 0.03137 -0.00152 AFIX 43 H12 2 -0.208219 0.233442 0.358345 11.00000 -1.20000 AFIX 0 C13 1 -0.170220 0.309194 0.353214 11.00000 0.05459 0.02411 = 0.05906 0.00062 0.02853 -0.00068 AFIX 43 H13 2 -0.238607 0.318678 0.405297 11.00000 -1.20000 AFIX 0 C14 1 -0.087466 0.346637 0.304207 11.00000 0.03687 0.02157 = 0.03695 0.00035 0.00824 0.00199 C15 1 -0.098714 0.400476 0.327333 11.00000 0.03164 0.02279 = 0.03087 -0.00106 0.01039 0.00184 C16 1 -0.199378 0.462564 0.451256 11.00000 0.03306 0.02194 = 0.02780 -0.00192 0.01094 -0.00243 AFIX 23 H16A 2 -0.148931 0.460671 0.532142 11.00000 -1.20000 H16B 2 -0.298655 0.472691 0.459452 11.00000 -1.20000 AFIX 0 C17 1 -0.131172 0.502862 0.382296 11.00000 0.02875 0.02191 = 0.02556 0.00088 0.00695 -0.00016 C18 1 -0.158895 0.553528 0.407940 11.00000 0.03166 0.02487 = 0.02678 0.00050 0.00912 0.00040 AFIX 43 H18 2 -0.221275 0.561632 0.466112 11.00000 -1.20000 AFIX 0 MOLE 2 O6 3 0.630466 0.664540 0.145100 11.00000 0.04668 0.02127 = 0.04132 0.00172 0.02228 -0.00189 O7 3 0.447953 0.642234 0.291915 11.00000 0.04573 0.02230 = 0.04362 -0.00350 0.02393 0.00131 O8 3 0.382654 0.465127 0.389466 11.00000 0.09161 0.03021 = 0.05293 -0.00671 0.04873 -0.01094 O9 3 0.412100 0.387666 0.326752 11.00000 0.05351 0.02398 = 0.03796 0.00133 0.02115 -0.00478 O10 3 0.651207 0.433757 0.063218 11.00000 0.05511 0.02270 = 0.05245 -0.00317 0.03397 -0.00607 C19 1 0.739062 0.677847 0.071338 11.00000 0.04611 0.02418 = 0.04938 0.00318 0.02064 -0.00354 AFIX 137 H19A 2 0.828927 0.662238 0.103119 11.00000 -1.50000 H19B 2 0.749763 0.715041 0.069958 11.00000 -1.50000 H19C 2 0.712963 0.665388 -0.009643 11.00000 -1.50000 AFIX 0 C20 1 0.362192 0.631405 0.385390 11.00000 0.04692 0.03172 = 0.04282 -0.00414 0.02465 -0.00080 AFIX 137 H20A 2 0.282244 0.609792 0.355047 11.00000 -1.50000 H20B 2 0.326168 0.663408 0.415783 11.00000 -1.50000 H20C 2 0.419093 0.613556 0.449722 11.00000 -1.50000 AFIX 0 C21 1 0.604748 0.613824 0.157795 11.00000 0.03402 0.02229 = 0.03027 0.00143 0.00810 -0.00269 C22 1 0.507307 0.601376 0.239399 11.00000 0.03180 0.02229 = 0.03004 -0.00310 0.00960 0.00129 C23 1 0.477414 0.551229 0.262626 11.00000 0.03077 0.02507 = 0.02962 -0.00118 0.01177 -0.00084 AFIX 43 H23 2 0.412504 0.543250 0.318882 11.00000 -1.20000 AFIX 0 C24 1 0.542253 0.511733 0.203697 11.00000 0.02736 0.02251 = 0.02548 0.00035 0.00522 -0.00126 C25 1 0.515890 0.457223 0.222601 11.00000 0.03055 0.02178 = 0.02861 -0.00038 0.00819 -0.00112 C26 1 0.433867 0.439504 0.315751 11.00000 0.04670 0.02553 = 0.03225 0.00071 0.01512 -0.00524 C27 1 0.463959 0.353129 0.251721 11.00000 0.03764 0.02379 = 0.03816 0.00249 0.01052 0.00056 C28 1 0.434036 0.302256 0.270698 11.00000 0.04730 0.02537 = 0.04955 0.00742 0.01475 -0.00291 AFIX 43 H28 2 0.379647 0.292514 0.333304 11.00000 -1.20000 AFIX 0 C29 1 0.484328 0.266059 0.197446 11.00000 0.05518 0.02042 = 0.06563 0.00533 0.01608 -0.00115 AFIX 43 H29 2 0.465263 0.230969 0.209882 11.00000 -1.20000 AFIX 0 C30 1 0.562933 0.280440 0.105245 11.00000 0.06140 0.02486 = 0.06814 -0.00155 0.02863 -0.00063 AFIX 43 H30 2 0.595905 0.255143 0.054372 11.00000 -1.20000 AFIX 0 C31 1 0.593327 0.331069 0.087141 11.00000 0.05173 0.02604 = 0.05223 -0.00032 0.02281 -0.00046 AFIX 43 H31 2 0.647748 0.340639 0.024425 11.00000 -1.20000 AFIX 0 C32 1 0.543624 0.368489 0.161667 11.00000 0.03656 0.02062 = 0.04212 0.00181 0.00933 0.00015 C33 1 0.570941 0.422202 0.150736 11.00000 0.03141 0.02536 = 0.03143 0.00281 0.01152 -0.00099 C34 1 0.707373 0.484246 0.054095 11.00000 0.03198 0.02232 = 0.02887 -0.00192 0.01078 -0.00263 AFIX 23 H34A 2 0.701183 0.493866 -0.030989 11.00000 -1.20000 H34B 2 0.809090 0.483723 0.084321 11.00000 -1.20000 AFIX 0 C35 1 0.634630 0.524464 0.120030 11.00000 0.02888 0.02427 = 0.02793 -0.00154 0.00733 -0.00098 C36 1 0.666416 0.575337 0.097611 11.00000 0.03102 0.02697 = 0.02805 0.00075 0.01223 -0.00209 AFIX 43 H36 2 0.730585 0.583443 0.040845 11.00000 -1.20000 HKLF 4 REM test in P2(1)/c REM R1 = 0.0498 for 3794 Fo > 4sig(Fo) and 0.1175 for all 7494 data REM 419 parameters refined using 0 restraints END WGHT 0.0701 0.0000 REM Highest difference peak 0.265, deepest hole -0.255, 1-sigma level 0.051 Q1 1 -0.1004 0.3119 0.4045 11.00000 0.05 0.26 Q2 1 -0.0389 0.4619 0.2792 11.00000 0.05 0.24 Q3 1 -0.1266 0.4114 0.4478 11.00000 0.05 0.24 Q4 1 0.6560 0.3297 0.1471 11.00000 0.05 0.23 Q5 1 0.5511 0.6100 0.1938 11.00000 0.05 0.23 Q6 1 -0.0960 0.4940 0.3426 11.00000 0.05 0.23 Q7 1 0.6586 0.5053 0.0821 11.00000 0.05 0.22 Q8 1 -0.0230 0.4192 0.3184 11.00000 0.05 0.22 Q9 1 0.1641 0.6591 0.1005 11.00000 0.05 0.22 Q10 1 0.5260 0.4384 0.1799 11.00000 0.05 0.22 Q11 1 -0.0465 0.5852 0.3070 11.00000 0.05 0.21 Q12 1 0.7176 0.4326 0.1164 11.00000 0.05 0.21 Q13 1 -0.0417 0.3426 0.2654 11.00000 0.05 0.20 Q14 1 0.0838 0.4467 0.0884 11.00000 0.05 0.20 Q15 1 0.5703 0.3511 0.1333 11.00000 0.05 0.20 Q16 1 -0.0953 0.3701 0.3252 11.00000 0.05 0.20 Q17 1 0.4981 0.5323 0.2230 11.00000 0.05 0.20 Q18 1 0.7202 0.3331 0.0858 11.00000 0.05 0.20 Q19 1 0.5771 0.5219 0.1558 11.00000 0.05 0.19 Q20 1 -0.0115 0.5075 0.2581 11.00000 0.05 0.19 ; 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 -0.11372(16) 0.64294(5) 0.36775(14) 0.0364(4) Uani 1 1 d . . . O2 O 0.04714(16) 0.62040(5) 0.20370(13) 0.0338(3) Uani 1 1 d . . . O3 O 0.16051(19) 0.44352(6) 0.14235(15) 0.0475(4) Uani 1 1 d . . . O4 O 0.09395(17) 0.36591(5) 0.17761(14) 0.0384(4) Uani 1 1 d . . . O5 O -0.19930(16) 0.41256(5) 0.39757(14) 0.0373(4) Uani 1 1 d . . . C1 C -0.2092(2) 0.65689(8) 0.4524(2) 0.0372(5) Uani 1 1 d . . . H1A H -0.3047 0.6447 0.4253 0.056 Uiso 1 1 calc R . . H1B H -0.2105 0.6941 0.4606 0.056 Uiso 1 1 calc R . . H1C H -0.1778 0.6414 0.5295 0.056 Uiso 1 1 calc R . . C2 C 0.1209(3) 0.60951(8) 0.1027(2) 0.0375(5) Uani 1 1 d . . . H2A H 0.2106 0.5923 0.1285 0.056 Uiso 1 1 calc R . . H2B H 0.1405 0.6414 0.0622 0.056 Uiso 1 1 calc R . . H2C H 0.0625 0.5873 0.0480 0.056 Uiso 1 1 calc R . . C3 C -0.0956(2) 0.59210(7) 0.34868(18) 0.0278(4) Uani 1 1 d . . . C4 C -0.0058(2) 0.57969(7) 0.26122(17) 0.0267(4) Uani 1 1 d . . . C5 C 0.0239(2) 0.52954(7) 0.23744(16) 0.0255(4) Uani 1 1 d . . . H5 H 0.0865 0.5215 0.1794 0.031 Uiso 1 1 calc R . . C6 C -0.0383(2) 0.49019(7) 0.29906(17) 0.0244(4) Uani 1 1 d . . . C7 C -0.0161(2) 0.43546(7) 0.27693(17) 0.0251(4) Uani 1 1 d . . . C8 C 0.0834(2) 0.41767(7) 0.19707(19) 0.0329(5) Uani 1 1 d . . . C9 C 0.0103(2) 0.33126(7) 0.22878(19) 0.0320(4) Uani 1 1 d . . . C10 C 0.0296(3) 0.28052(8) 0.2010(2) 0.0424(5) Uani 1 1 d . . . H10 H 0.0979 0.2708 0.1490 0.051 Uiso 1 1 calc R . . C11 C -0.0523(3) 0.24431(8) 0.2503(2) 0.0483(6) Uani 1 1 d . . . H11 H -0.0403 0.2092 0.2326 0.058 Uiso 1 1 calc R . . C12 C -0.1518(3) 0.25875(8) 0.3255(3) 0.0538(7) Uani 1 1 d . . . H12 H -0.2082 0.2334 0.3583 0.065 Uiso 1 1 calc R . . C13 C -0.1702(3) 0.30919(8) 0.3532(2) 0.0444(6) Uani 1 1 d . . . H13 H -0.2386 0.3187 0.4053 0.053 Uiso 1 1 calc R . . C14 C -0.0875(2) 0.34664(7) 0.30421(19) 0.0315(4) Uani 1 1 d . . . C15 C -0.0987(2) 0.40048(7) 0.32733(18) 0.0279(4) Uani 1 1 d . . . C16 C -0.1994(2) 0.46256(7) 0.45126(17) 0.0271(4) Uani 1 1 d . . . H16A H -0.1489 0.4607 0.5321 0.032 Uiso 1 1 calc R . . H16B H -0.2987 0.4727 0.4595 0.032 Uiso 1 1 calc R . . C17 C -0.1312(2) 0.50286(7) 0.38230(17) 0.0251(4) Uani 1 1 d . . . C18 C -0.1589(2) 0.55353(7) 0.40794(17) 0.0274(4) Uani 1 1 d . . . H18 H -0.2213 0.5616 0.4661 0.033 Uiso 1 1 calc R . . O6 O 0.63047(16) 0.66454(5) 0.14510(13) 0.0352(3) Uani 1 1 d . . . O7 O 0.44795(16) 0.64223(5) 0.29191(14) 0.0359(4) Uani 1 1 d . . . O8 O 0.3827(2) 0.46513(6) 0.38947(16) 0.0555(5) Uani 1 1 d . . . O9 O 0.41210(17) 0.38767(5) 0.32675(13) 0.0374(4) Uani 1 1 d . . . O10 O 0.65121(17) 0.43376(5) 0.06322(15) 0.0415(4) Uani 1 1 d . . . C19 C 0.7391(2) 0.67785(7) 0.0713(2) 0.0388(5) Uani 1 1 d . . . H19A H 0.8289 0.6622 0.1031 0.058 Uiso 1 1 calc R . . H19B H 0.7498 0.7150 0.0700 0.058 Uiso 1 1 calc R . . H19C H 0.7130 0.6654 -0.0096 0.058 Uiso 1 1 calc R . . C20 C 0.3622(3) 0.63141(8) 0.3854(2) 0.0391(5) Uani 1 1 d . . . H20A H 0.2822 0.6098 0.3550 0.059 Uiso 1 1 calc R . . H20B H 0.3262 0.6634 0.4158 0.059 Uiso 1 1 calc R . . H20C H 0.4191 0.6136 0.4497 0.059 Uiso 1 1 calc R . . C21 C 0.6047(2) 0.61382(7) 0.15779(18) 0.0285(4) Uani 1 1 d . . . C22 C 0.5073(2) 0.60138(7) 0.23940(17) 0.0276(4) Uani 1 1 d . . . C23 C 0.4774(2) 0.55123(7) 0.26263(17) 0.0279(4) Uani 1 1 d . . . H23 H 0.4125 0.5432 0.3189 0.033 Uiso 1 1 calc R . . C24 C 0.5423(2) 0.51173(7) 0.20370(17) 0.0249(4) Uani 1 1 d . . . C25 C 0.5159(2) 0.45722(7) 0.22260(17) 0.0266(4) Uani 1 1 d . . . C26 C 0.4339(2) 0.43950(7) 0.31575(19) 0.0341(5) Uani 1 1 d . . . C27 C 0.4640(2) 0.35313(7) 0.25172(19) 0.0327(5) Uani 1 1 d . . . C28 C 0.4340(3) 0.30226(8) 0.2707(2) 0.0401(5) Uani 1 1 d . . . H28 H 0.3796 0.2925 0.3333 0.048 Uiso 1 1 calc R . . C29 C 0.4843(3) 0.26606(8) 0.1974(2) 0.0464(6) Uani 1 1 d . . . H29 H 0.4653 0.2310 0.2099 0.056 Uiso 1 1 calc R . . C30 C 0.5629(3) 0.28044(8) 0.1052(3) 0.0500(6) Uani 1 1 d . . . H30 H 0.5959 0.2551 0.0544 0.060 Uiso 1 1 calc R . . C31 C 0.5933(3) 0.33107(8) 0.0871(2) 0.0422(6) Uani 1 1 d . . . H31 H 0.6477 0.3406 0.0244 0.051 Uiso 1 1 calc R . . C32 C 0.5436(2) 0.36849(7) 0.1617(2) 0.0327(4) Uani 1 1 d . . . C33 C 0.5709(2) 0.42220(7) 0.15074(18) 0.0288(4) Uani 1 1 d . . . C34 C 0.7074(2) 0.48425(7) 0.05410(17) 0.0272(4) Uani 1 1 d . . . H34A H 0.7012 0.4939 -0.0310 0.033 Uiso 1 1 calc R . . H34B H 0.8091 0.4837 0.0843 0.033 Uiso 1 1 calc R . . C35 C 0.6346(2) 0.52446(7) 0.12003(17) 0.0267(4) Uani 1 1 d . . . C36 C 0.6664(2) 0.57534(7) 0.09761(17) 0.0281(4) Uani 1 1 d . . . H36 H 0.7306 0.5834 0.0408 0.034 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 0.0491(9) 0.0199(6) 0.0438(9) -0.0002(6) 0.0234(7) 0.0029(6) O2 0.0435(9) 0.0208(6) 0.0404(8) 0.0036(6) 0.0210(7) 0.0006(6) O3 0.0639(11) 0.0275(7) 0.0581(11) -0.0004(7) 0.0411(9) -0.0012(7) O4 0.0479(9) 0.0222(7) 0.0493(9) -0.0033(6) 0.0264(7) 0.0003(6) O5 0.0453(9) 0.0218(7) 0.0492(9) -0.0039(6) 0.0261(7) -0.0025(6) C1 0.0455(13) 0.0279(10) 0.0410(12) -0.0036(8) 0.0187(10) 0.0050(9) C2 0.0471(13) 0.0302(10) 0.0390(12) 0.0038(8) 0.0233(10) 0.0005(9) C3 0.0334(11) 0.0191(8) 0.0321(10) -0.0003(7) 0.0096(9) 0.0024(7) C4 0.0317(10) 0.0204(8) 0.0292(10) 0.0034(7) 0.0096(8) -0.0018(7) C5 0.0291(10) 0.0246(9) 0.0241(9) 0.0000(7) 0.0099(8) 0.0008(7) C6 0.0262(10) 0.0216(8) 0.0262(10) 0.0005(7) 0.0055(8) 0.0005(7) C7 0.0293(10) 0.0196(8) 0.0272(10) -0.0015(7) 0.0063(8) -0.0001(7) C8 0.0419(12) 0.0235(9) 0.0353(11) -0.0011(8) 0.0138(9) 0.0000(8) C9 0.0355(12) 0.0246(9) 0.0369(11) -0.0001(8) 0.0085(9) 0.0001(8) C10 0.0504(14) 0.0267(10) 0.0525(14) -0.0051(9) 0.0175(11) 0.0050(9) C11 0.0600(16) 0.0216(10) 0.0661(17) -0.0010(10) 0.0203(13) 0.0020(9) C12 0.0673(18) 0.0230(11) 0.0761(19) 0.0042(10) 0.0314(15) -0.0015(10) C13 0.0546(15) 0.0241(10) 0.0591(15) 0.0006(9) 0.0285(12) -0.0007(9) C14 0.0369(11) 0.0216(9) 0.0369(11) 0.0004(8) 0.0082(9) 0.0020(8) C15 0.0316(10) 0.0228(9) 0.0309(10) -0.0011(7) 0.0104(8) 0.0018(7) C16 0.0331(11) 0.0219(8) 0.0278(10) -0.0019(7) 0.0109(8) -0.0024(7) C17 0.0288(10) 0.0219(8) 0.0256(10) 0.0009(7) 0.0069(8) -0.0002(7) C18 0.0317(11) 0.0249(9) 0.0268(10) 0.0005(7) 0.0091(8) 0.0004(7) O6 0.0467(9) 0.0213(7) 0.0413(9) 0.0017(6) 0.0223(7) -0.0019(6) O7 0.0457(9) 0.0223(7) 0.0436(9) -0.0035(6) 0.0239(7) 0.0013(6) O8 0.0916(14) 0.0302(8) 0.0529(11) -0.0067(7) 0.0487(10) -0.0109(8) O9 0.0535(10) 0.0240(7) 0.0380(8) 0.0013(6) 0.0211(7) -0.0048(6) O10 0.0551(10) 0.0227(7) 0.0525(10) -0.0032(6) 0.0340(8) -0.0061(6) C19 0.0461(13) 0.0242(9) 0.0494(14) 0.0032(9) 0.0206(11) -0.0035(9) C20 0.0469(13) 0.0317(11) 0.0428(13) -0.0041(9) 0.0247(11) -0.0008(9) C21 0.0340(11) 0.0223(9) 0.0303(10) 0.0014(7) 0.0081(9) -0.0027(7) C22 0.0318(10) 0.0223(9) 0.0300(10) -0.0031(7) 0.0096(8) 0.0013(7) C23 0.0308(11) 0.0251(9) 0.0296(10) -0.0012(7) 0.0118(8) -0.0008(7) C24 0.0274(10) 0.0225(8) 0.0255(10) 0.0003(7) 0.0052(8) -0.0013(7) C25 0.0305(10) 0.0218(9) 0.0286(10) -0.0004(7) 0.0082(8) -0.0011(7) C26 0.0467(13) 0.0255(9) 0.0323(11) 0.0007(8) 0.0151(10) -0.0052(8) C27 0.0376(12) 0.0238(9) 0.0382(12) 0.0025(8) 0.0105(9) 0.0006(8) C28 0.0473(14) 0.0254(10) 0.0496(14) 0.0074(9) 0.0148(11) -0.0029(9) C29 0.0552(15) 0.0204(9) 0.0656(17) 0.0053(10) 0.0161(13) -0.0011(9) C30 0.0614(16) 0.0249(10) 0.0681(17) -0.0016(10) 0.0286(14) -0.0006(10) C31 0.0517(14) 0.0260(10) 0.0522(14) -0.0003(9) 0.0228(11) -0.0005(9) C32 0.0366(11) 0.0206(9) 0.0421(12) 0.0018(8) 0.0093(9) 0.0002(8) C33 0.0314(11) 0.0254(9) 0.0314(11) 0.0028(7) 0.0115(8) -0.0010(7) C34 0.0320(11) 0.0223(8) 0.0289(10) -0.0019(7) 0.0108(8) -0.0026(7) C35 0.0289(10) 0.0243(9) 0.0279(10) -0.0015(7) 0.0073(8) -0.0010(7) C36 0.0310(11) 0.0270(9) 0.0280(10) 0.0008(7) 0.0122(8) -0.0021(7) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 C3 1.363(2) . ? O1 C1 1.427(2) . ? O2 C4 1.370(2) . ? O2 C2 1.424(2) . ? O3 C8 1.209(2) . ? O4 C9 1.370(2) . ? O4 C8 1.379(2) . ? O5 C15 1.336(2) . ? O5 C16 1.444(2) . ? C3 C18 1.381(3) . ? C3 C4 1.404(3) . ? C4 C5 1.376(2) . ? C5 C6 1.406(3) . ? C6 C17 1.389(3) . ? C6 C7 1.474(2) . ? C7 C15 1.365(3) . ? C7 C8 1.445(3) . ? C9 C14 1.379(3) . ? C9 C10 1.382(3) . ? C10 C11 1.378(3) . ? C11 C12 1.382(3) . ? C12 C13 1.373(3) . ? C13 C14 1.403(3) . ? C14 C15 1.440(3) . ? C16 C17 1.496(3) . ? C17 C18 1.389(3) . ? O6 C21 1.361(2) . ? O6 C19 1.429(2) . ? O7 C22 1.371(2) . ? O7 C20 1.423(3) . ? O8 C26 1.208(3) . ? O9 C27 1.364(2) . ? O9 C26 1.381(2) . ? O10 C33 1.340(2) . ? O10 C34 1.433(2) . ? C21 C36 1.378(3) . ? C21 C22 1.406(3) . ? C22 C23 1.375(3) . ? C23 C24 1.404(3) . ? C24 C35 1.390(3) . ? C24 C25 1.469(2) . ? C25 C33 1.362(3) . ? C25 C26 1.445(3) . ? C27 C28 1.384(3) . ? C27 C32 1.385(3) . ? C28 C29 1.374(3) . ? C29 C30 1.391(3) . ? C30 C31 1.377(3) . ? C31 C32 1.403(3) . ? C32 C33 1.438(3) . ? C34 C35 1.497(3) . ? C35 C36 1.395(3) . ? 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 C3 O1 C1 117.03(15) . . ? C4 O2 C2 117.10(15) . . ? C9 O4 C8 122.04(16) . . ? C15 O5 C16 119.62(15) . . ? O1 C3 C18 124.81(17) . . ? O1 C3 C4 115.60(16) . . ? C18 C3 C4 119.59(17) . . ? O2 C4 C5 124.03(17) . . ? O2 C4 C3 115.41(16) . . ? C5 C4 C3 120.56(16) . . ? C4 C5 C6 119.99(17) . . ? C17 C6 C5 118.97(16) . . ? C17 C6 C7 117.23(16) . . ? C5 C6 C7 123.75(17) . . ? C15 C7 C8 118.67(17) . . ? C15 C7 C6 119.02(17) . . ? C8 C7 C6 122.17(16) . . ? O3 C8 O4 114.36(18) . . ? O3 C8 C7 127.05(18) . . ? O4 C8 C7 118.59(16) . . ? O4 C9 C14 121.24(17) . . ? O4 C9 C10 116.49(19) . . ? C14 C9 C10 122.27(19) . . ? C11 C10 C9 118.5(2) . . ? C10 C11 C12 120.4(2) . . ? C13 C12 C11 120.9(2) . . ? C12 C13 C14 119.6(2) . . ? C9 C14 C13 118.34(18) . . ? C9 C14 C15 117.68(17) . . ? C13 C14 C15 123.98(19) . . ? O5 C15 C7 124.04(17) . . ? O5 C15 C14 114.17(16) . . ? C7 C15 C14 121.75(18) . . ? O5 C16 C17 113.80(15) . . ? C18 C17 C6 120.97(16) . . ? C18 C17 C16 117.75(17) . . ? C6 C17 C16 121.22(16) . . ? C3 C18 C17 119.87(18) . . ? C21 O6 C19 116.50(15) . . ? C22 O7 C20 116.99(15) . . ? C27 O9 C26 122.03(16) . . ? C33 O10 C34 120.21(15) . . ? O6 C21 C36 125.00(18) . . ? O6 C21 C22 115.57(16) . . ? C36 C21 C22 119.44(17) . . ? O7 C22 C23 124.24(17) . . ? O7 C22 C21 115.24(16) . . ? C23 C22 C21 120.52(16) . . ? C22 C23 C24 120.39(17) . . ? C35 C24 C23 118.65(17) . . ? C35 C24 C25 117.35(16) . . ? C23 C24 C25 123.99(17) . . ? C33 C25 C26 118.85(17) . . ? C33 C25 C24 119.18(17) . . ? C26 C25 C24 121.97(16) . . ? O8 C26 O9 114.26(18) . . ? O8 C26 C25 127.22(19) . . ? O9 C26 C25 118.50(17) . . ? O9 C27 C28 116.80(19) . . ? O9 C27 C32 121.29(17) . . ? C28 C27 C32 121.90(19) . . ? C29 C28 C27 118.9(2) . . ? C28 C29 C30 120.5(2) . . ? C31 C30 C29 120.5(2) . . ? C30 C31 C32 119.8(2) . . ? C27 C32 C31 118.49(18) . . ? C27 C32 C33 117.58(18) . . ? C31 C32 C33 123.93(19) . . ? O10 C33 C25 124.46(17) . . ? O10 C33 C32 113.85(16) . . ? C25 C33 C32 121.67(18) . . ? O10 C34 C35 114.94(16) . . ? C24 C35 C36 120.94(17) . . ? C24 C35 C34 121.38(16) . . ? C36 C35 C34 117.65(17) . . ? C21 C36 C35 120.01(17) . . ? _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 29.26 _diffrn_measured_fraction_theta_full 0.985 _refine_diff_density_max 0.265 _refine_diff_density_min -0.255 _refine_diff_density_rms 0.051 _database_code_depnum_ccdc_archive 'CCDC 942498' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_mnb65 #TrackingRef 'mnb65.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H10 O3' _chemical_formula_weight 250.24 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 P212121 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 6.8656(14) _cell_length_b 12.618(3) _cell_length_c 13.593(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1177.6(4) _cell_formula_units_Z 4 _cell_measurement_temperature 170(2) _cell_measurement_reflns_used 39933 _cell_measurement_theta_min 8.8 _cell_measurement_theta_max 126.9 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.48 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.411 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 520 _exptl_absorpt_coefficient_mu 0.098 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.9692 _exptl_absorpt_correction_T_max 0.9932 _exptl_absorpt_process_details 'face indexed' _exptl_special_details ; ? ; _diffrn_ambient_temperature 170(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13256 _diffrn_reflns_av_R_equivalents 0.0702 _diffrn_reflns_av_sigmaI/netI 0.0475 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.20 _diffrn_reflns_theta_max 29.44 _reflns_number_total 3246 _reflns_number_gt 2465 _reflns_threshold_expression >2\s(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _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^ > 2\s(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^)+(0.0654P)^2^+0.1665P] 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 3246 _refine_ls_number_parameters 173 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0693 _refine_ls_R_factor_gt 0.0469 _refine_ls_wR_factor_ref 0.1276 _refine_ls_wR_factor_gt 0.1147 _refine_ls_goodness_of_fit_ref 1.053 _refine_ls_restrained_S_all 1.053 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _iucr_refine_instructions_details ; TITL mnb65 in P2(1)2(1)2(1) CELL 0.71073 6.8656 12.6179 13.5934 90.000 90.000 90.000 ZERR 4.00 0.0014 0.0025 0.0027 0.000 0.000 0.000 LATT -1 SYMM 1/2 - X, - Y, 1/2 + Z SYMM 1/2 + X, 1/2 - Y, - Z SYMM - X, 1/2 + Y, 1/2 - Z SFAC C H O UNIT 64 40 12 MERG 2 FMAP 2 PLAN -5 TEMP -103 SIZE 0.48 0.19 0.18 ACTA L.S. 24 WGHT 0.065400 0.166500 FVAR 0.85203 O1 3 0.366072 0.994785 0.461023 11.00000 0.04988 0.02677 = 0.03364 -0.01008 0.00702 -0.00215 O2 3 0.364758 0.938869 0.306305 11.00000 0.03535 0.02089 = 0.02402 -0.00247 0.00343 0.00082 O3 3 0.379437 0.633078 0.404092 11.00000 0.02917 0.02225 = 0.02212 0.00266 -0.00116 0.00145 C1 1 0.374831 0.788574 0.627025 11.00000 0.02080 0.04140 = 0.02047 -0.00515 0.00143 -0.00058 AFIX 43 H1 2 0.374406 0.861621 0.643955 11.00000 -1.20000 AFIX 0 C2 1 0.375743 0.756956 0.527915 11.00000 0.01925 0.03304 = 0.02010 0.00030 -0.00160 -0.00096 C3 1 0.374731 0.809158 0.433963 11.00000 0.01981 0.02483 = 0.02164 -0.00050 0.00064 0.00014 C4 1 0.370392 0.919294 0.406997 11.00000 0.02622 0.02434 = 0.02567 -0.00137 0.00305 -0.00051 C5 1 0.368815 0.859972 0.236488 11.00000 0.02281 0.02309 = 0.02273 -0.00174 0.00072 0.00113 C6 1 0.362228 0.891826 0.138789 11.00000 0.03299 0.02672 = 0.02765 0.00588 0.00050 0.00243 AFIX 43 H6 2 0.354250 0.964906 0.122468 11.00000 -1.20000 AFIX 0 C7 1 0.367410 0.816113 0.065794 11.00000 0.03507 0.03555 = 0.01952 0.00287 0.00005 0.00217 AFIX 43 H7 2 0.362053 0.837512 -0.001156 11.00000 -1.20000 AFIX 0 C8 1 0.380408 0.708415 0.088620 11.00000 0.03262 0.03004 = 0.02292 -0.00393 -0.00031 0.00170 AFIX 43 H8 2 0.386646 0.657199 0.037491 11.00000 -1.20000 AFIX 0 C9 1 0.384152 0.676702 0.185857 11.00000 0.02890 0.02224 = 0.02275 -0.00281 0.00087 0.00230 AFIX 43 H9 2 0.391734 0.603476 0.201651 11.00000 -1.20000 AFIX 0 C10 1 0.376815 0.752055 0.260975 11.00000 0.02065 0.02279 = 0.02041 0.00059 0.00297 0.00128 C11 1 0.377498 0.732014 0.364300 11.00000 0.01917 0.02342 = 0.02243 -0.00071 -0.00041 -0.00071 C12 1 0.378174 0.649651 0.505311 11.00000 0.02363 0.03272 = 0.01902 0.00277 0.00117 0.00054 C13 1 0.379465 0.570587 0.576086 11.00000 0.03097 0.03423 = 0.02781 0.00848 0.00211 0.00196 AFIX 43 H13 2 0.382522 0.497554 0.559174 11.00000 -1.20000 AFIX 0 C14 1 0.376030 0.604477 0.672827 11.00000 0.02927 0.05270 = 0.02467 0.01230 -0.00060 -0.00088 AFIX 43 H14 2 0.374602 0.552719 0.723576 11.00000 -1.20000 AFIX 0 C15 1 0.374562 0.711961 0.699306 11.00000 0.01959 0.05825 = 0.02114 0.00138 0.00109 0.00053 C16 1 0.373295 0.743508 0.806479 11.00000 0.03032 0.07908 = 0.01844 -0.00295 0.00242 0.00046 AFIX 137 H16A 2 0.333476 0.817817 0.812425 11.00000 -1.50000 H16B 2 0.504193 0.734657 0.834032 11.00000 -1.50000 H16C 2 0.281393 0.698522 0.842525 11.00000 -1.50000 HKLF 4 REM mnb65 in P2(1)2(1)2(1) REM R1 = 0.0469 for 2465 Fo > 4sig(Fo) and 0.0693 for all 3246 data REM 173 parameters refined using 0 restraints END WGHT 0.0648 0.1687 REM Highest difference peak 0.382, deepest hole -0.210, 1-sigma level 0.051 Q1 1 0.3800 0.7832 0.4831 11.00000 0.05 0.38 Q2 1 0.3733 0.8729 0.5970 11.00000 0.05 0.37 Q3 1 0.3790 0.7030 0.5400 11.00000 0.05 0.32 Q4 1 0.3777 0.7287 0.7463 11.00000 0.05 0.29 Q5 1 0.3913 0.7597 0.6596 11.00000 0.05 0.29 ; 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 0.3661(3) 0.99478(9) 0.46102(10) 0.0368(3) Uani 1 1 d . . . O2 O 0.3648(3) 0.93887(9) 0.30630(9) 0.0267(3) Uani 1 1 d . . . O3 O 0.3794(3) 0.63308(8) 0.40409(8) 0.0245(3) Uani 1 1 d . . . C1 C 0.3748(4) 0.78857(16) 0.62703(12) 0.0276(4) Uani 1 1 d . . . H1 H 0.3744 0.8616 0.6440 0.033 Uiso 1 1 calc R . . C2 C 0.3757(4) 0.75696(13) 0.52792(11) 0.0241(3) Uani 1 1 d . . . C3 C 0.3747(3) 0.80916(12) 0.43396(12) 0.0221(3) Uani 1 1 d . . . C4 C 0.3704(4) 0.91929(12) 0.40700(13) 0.0254(3) Uani 1 1 d . . . C5 C 0.3688(3) 0.85997(12) 0.23649(12) 0.0229(3) Uani 1 1 d . . . C6 C 0.3622(4) 0.89183(14) 0.13879(13) 0.0291(4) Uani 1 1 d . . . H6 H 0.3542 0.9649 0.1225 0.035 Uiso 1 1 calc R . . C7 C 0.3674(4) 0.81611(14) 0.06579(13) 0.0300(4) Uani 1 1 d . . . H7 H 0.3621 0.8375 -0.0012 0.036 Uiso 1 1 calc R . . C8 C 0.3804(4) 0.70841(13) 0.08862(13) 0.0285(4) Uani 1 1 d . . . H8 H 0.3866 0.6572 0.0375 0.034 Uiso 1 1 calc R . . C9 C 0.3842(3) 0.67670(12) 0.18586(12) 0.0246(3) Uani 1 1 d . . . H9 H 0.3917 0.6035 0.2017 0.030 Uiso 1 1 calc R . . C10 C 0.3768(3) 0.75205(11) 0.26097(12) 0.0213(3) Uani 1 1 d . . . C11 C 0.3775(4) 0.73201(13) 0.36430(11) 0.0217(3) Uani 1 1 d . . . C12 C 0.3782(4) 0.64965(13) 0.50531(12) 0.0251(3) Uani 1 1 d . . . C13 C 0.3795(4) 0.57059(15) 0.57609(13) 0.0310(4) Uani 1 1 d . . . H13 H 0.3825 0.4976 0.5592 0.037 Uiso 1 1 calc R . . C14 C 0.3760(4) 0.60448(17) 0.67283(14) 0.0355(4) Uani 1 1 d . . . H14 H 0.3746 0.5527 0.7236 0.043 Uiso 1 1 calc R . . C15 C 0.3746(4) 0.71196(17) 0.69931(13) 0.0330(4) Uani 1 1 d . . . C16 C 0.3733(4) 0.7435(2) 0.80648(14) 0.0426(5) Uani 1 1 d . . . H16A H 0.3335 0.8178 0.8124 0.064 Uiso 1 1 calc R . . H16B H 0.5042 0.7347 0.8340 0.064 Uiso 1 1 calc R . . H16C H 0.2814 0.6985 0.8425 0.064 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 0.0499(8) 0.0268(6) 0.0336(7) -0.0101(5) 0.0070(9) -0.0022(8) O2 0.0353(7) 0.0209(5) 0.0240(6) -0.0025(4) 0.0034(8) 0.0008(7) O3 0.0292(6) 0.0223(5) 0.0221(6) 0.0027(4) -0.0012(7) 0.0015(6) C1 0.0208(7) 0.0414(9) 0.0205(8) -0.0052(7) 0.0014(10) -0.0006(11) C2 0.0193(7) 0.0330(8) 0.0201(7) 0.0003(6) -0.0016(11) -0.0010(8) C3 0.0198(6) 0.0248(7) 0.0216(7) -0.0005(5) 0.0006(9) 0.0001(9) C4 0.0262(8) 0.0243(7) 0.0257(8) -0.0014(6) 0.0031(10) -0.0005(10) C5 0.0228(7) 0.0231(7) 0.0227(7) -0.0017(6) 0.0007(9) 0.0011(9) C6 0.0330(10) 0.0267(7) 0.0276(8) 0.0059(6) 0.0005(10) 0.0024(9) C7 0.0351(9) 0.0356(9) 0.0195(7) 0.0029(6) 0.0000(10) 0.0022(10) C8 0.0326(9) 0.0300(8) 0.0229(8) -0.0039(6) -0.0003(10) 0.0017(10) C9 0.0289(8) 0.0222(7) 0.0228(7) -0.0028(6) 0.0009(9) 0.0023(8) C10 0.0207(7) 0.0228(7) 0.0204(7) 0.0006(6) 0.0030(10) 0.0013(8) C11 0.0192(7) 0.0234(7) 0.0224(8) -0.0007(6) -0.0004(9) -0.0007(9) C12 0.0236(8) 0.0327(8) 0.0190(7) 0.0028(6) 0.0012(8) 0.0005(10) C13 0.0310(9) 0.0342(9) 0.0278(9) 0.0085(7) 0.0021(11) 0.0020(13) C14 0.0293(9) 0.0527(10) 0.0247(8) 0.0123(8) -0.0006(10) -0.0009(12) C15 0.0196(8) 0.0583(11) 0.0211(8) 0.0014(8) 0.0011(10) 0.0005(12) C16 0.0303(10) 0.0791(15) 0.0184(8) -0.0029(9) 0.0024(12) 0.0005(14) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 C4 1.203(2) . ? O2 C5 1.3757(19) . ? O2 C4 1.391(2) . ? O3 C11 1.361(2) . ? O3 C12 1.392(2) . ? C1 C15 1.378(3) . ? C1 C2 1.405(2) . ? C2 C12 1.388(2) . ? C2 C3 1.437(2) . ? C3 C11 1.358(2) . ? C3 C4 1.438(2) . ? C5 C6 1.388(2) . ? C5 C10 1.403(2) . ? C6 C7 1.378(2) . ? C7 C8 1.397(2) . ? C8 C9 1.381(2) . ? C9 C10 1.396(2) . ? C10 C11 1.427(2) . ? C12 C13 1.386(2) . ? C13 C14 1.383(3) . ? C14 C15 1.403(3) . ? C15 C16 1.510(3) . ? 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 C5 O2 C4 123.34(13) . . ? C11 O3 C12 104.78(12) . . ? C15 C1 C2 118.97(18) . . ? C12 C2 C1 119.28(16) . . ? C12 C2 C3 104.50(13) . . ? C1 C2 C3 136.22(16) . . ? C11 C3 C2 106.92(13) . . ? C11 C3 C4 121.02(15) . . ? C2 C3 C4 132.06(14) . . ? O1 C4 O2 117.34(15) . . ? O1 C4 C3 127.61(17) . . ? O2 C4 C3 115.03(14) . . ? O2 C5 C6 116.73(14) . . ? O2 C5 C10 122.65(14) . . ? C6 C5 C10 120.62(15) . . ? C7 C6 C5 119.16(15) . . ? C6 C7 C8 121.08(16) . . ? C9 C8 C7 119.71(15) . . ? C8 C9 C10 120.13(15) . . ? C9 C10 C5 119.27(14) . . ? C9 C10 C11 126.80(14) . . ? C5 C10 C11 113.93(14) . . ? C3 C11 O3 112.37(14) . . ? C3 C11 C10 124.00(15) . . ? O3 C11 C10 123.63(14) . . ? C13 C12 C2 123.25(17) . . ? C13 C12 O3 125.31(16) . . ? C2 C12 O3 111.43(14) . . ? C14 C13 C12 115.94(18) . . ? C13 C14 C15 122.88(17) . . ? C1 C15 C14 119.67(17) . . ? C1 C15 C16 120.2(2) . . ? C14 C15 C16 120.15(18) . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 29.44 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.382 _refine_diff_density_min -0.210 _refine_diff_density_rms 0.051 _database_code_depnum_ccdc_archive 'CCDC 932991' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_MNB75 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H7 F O3' _chemical_formula_weight 218.18 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' F F 0.0171 0.0103 '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 7.1648(14) _cell_length_b 7.7947(16) _cell_length_c 8.6050(17) _cell_angle_alpha 74.65(3) _cell_angle_beta 80.31(3) _cell_angle_gamma 82.76(3) _cell_volume 455.13(16) _cell_formula_units_Z 2 _cell_measurement_temperature 170(2) _cell_measurement_reflns_used 5030 _cell_measurement_theta_min 6.4 _cell_measurement_theta_max 58.5 _exptl_crystal_description platelet _exptl_crystal_colour colourless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.592 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 224 _exptl_absorpt_coefficient_mu 0.128 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.9086 _exptl_absorpt_correction_T_max 0.9841 _exptl_absorpt_process_details 'face indexed' _exptl_special_details ; ? ; _diffrn_ambient_temperature 170(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5030 _diffrn_reflns_av_R_equivalents 0.0291 _diffrn_reflns_av_sigmaI/netI 0.0306 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 3.19 _diffrn_reflns_theta_max 29.25 _reflns_number_total 2442 _reflns_number_gt 1762 _reflns_threshold_expression >2\s(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _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^ > 2\s(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^)+(0.0814P)^2^+0.0618P] 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 2442 _refine_ls_number_parameters 146 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0687 _refine_ls_R_factor_gt 0.0486 _refine_ls_wR_factor_ref 0.1425 _refine_ls_wR_factor_gt 0.1293 _refine_ls_goodness_of_fit_ref 1.063 _refine_ls_restrained_S_all 1.063 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _iucr_refine_instructions_details ; TITL MNB75 in P-1 CELL 0.71073 7.1648 7.7947 8.6050 74.651 80.308 82.757 ZERR 2.00 0.0014 0.0016 0.0017 0.030 0.030 0.030 LATT 1 SFAC C H O F UNIT 24 14 6 2 MERG 2 FMAP 2 ACTA PLAN -5 L.S. 24 TEMP -103.00 WGHT 0.081400 0.061800 FVAR 1.48315 C1 1 0.081809 0.035370 0.725927 11.00000 0.02632 0.03701 = 0.03561 -0.00059 0.00352 -0.01015 AFIX 137 H1A 2 -0.051747 0.057753 0.708622 11.00000 -1.50000 H1B 2 0.093229 0.051102 0.833122 11.00000 -1.50000 H1C 2 0.128103 -0.087025 0.720631 11.00000 -1.50000 AFIX 0 C2 1 0.196472 0.162788 0.598033 11.00000 0.02012 0.03322 = 0.03166 -0.00683 0.00213 -0.00733 C3 1 0.127949 0.295129 0.480991 11.00000 0.01928 0.03332 = 0.03177 -0.00494 0.00062 -0.00608 AFIX 43 H3 2 -0.003866 0.317033 0.472469 11.00000 -1.20000 AFIX 0 C4 1 0.264189 0.398882 0.372123 11.00000 0.02304 0.02850 = 0.02624 -0.00345 -0.00007 -0.00478 C5 1 0.395066 0.600581 0.169863 11.00000 0.02579 0.02916 = 0.02689 -0.00544 0.00094 -0.00600 C6 1 0.417561 0.740322 0.033876 11.00000 0.03668 0.03292 = 0.03072 -0.00411 -0.00205 -0.00486 AFIX 43 H6 2 0.312052 0.805821 -0.014638 11.00000 -1.20000 AFIX 0 C7 1 0.602658 0.780492 -0.028653 11.00000 0.04433 0.03051 = 0.02939 -0.00295 0.00340 -0.01195 AFIX 43 H7 2 0.627801 0.876406 -0.121856 11.00000 -1.20000 AFIX 0 C8 1 0.750456 0.678652 0.046824 11.00000 0.03051 0.03531 = 0.03221 -0.00717 0.00726 -0.01426 C9 1 0.729510 0.540219 0.184168 11.00000 0.02648 0.03174 = 0.03119 -0.00630 0.00282 -0.01059 AFIX 43 H9 2 0.835274 0.475724 0.232951 11.00000 -1.20000 AFIX 0 C10 1 0.543661 0.500549 0.247194 11.00000 0.02574 0.02771 = 0.02580 -0.00610 0.00238 -0.00724 C11 1 0.454570 0.369636 0.380540 11.00000 0.02016 0.02836 = 0.02797 -0.00592 0.00218 -0.00640 C12 1 0.525102 0.231569 0.507309 11.00000 0.02037 0.02890 = 0.02892 -0.00731 0.00215 -0.00683 O1 3 0.222180 0.537996 0.246804 11.00000 0.02325 0.03313 = 0.03028 -0.00021 -0.00069 -0.00375 O2 3 0.686095 0.191470 0.535484 11.00000 0.02092 0.03732 = 0.03791 -0.00478 -0.00256 -0.00315 O3 3 0.385800 0.131259 0.612057 11.00000 0.02064 0.03121 = 0.03067 -0.00202 0.00079 -0.00683 F1 4 0.929315 0.719432 -0.020015 11.00000 0.03649 0.04891 = 0.04526 -0.00123 0.01104 -0.02115 HKLF 4 REM test in P-1 REM R1 = 0.0486 for 1762 Fo > 4sig(Fo) and 0.0687 for all 2442 data REM 146 parameters refined using 0 restraints END WGHT 0.0811 0.0625 REM Highest difference peak 0.314, deepest hole -0.289, 1-sigma level 0.055 Q1 1 0.2005 0.3455 0.4252 11.00000 0.05 0.31 Q2 1 0.5186 0.4340 0.3234 11.00000 0.05 0.31 Q3 1 0.7405 0.6055 0.1159 11.00000 0.05 0.26 Q4 1 0.3746 0.3857 0.3929 11.00000 0.05 0.26 Q5 1 0.1382 0.0993 0.6640 11.00000 0.05 0.25 ; 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 C1 C 0.0818(2) 0.0354(2) 0.7259(2) 0.0349(4) Uani 1 1 d . . . H1A H -0.0517 0.0578 0.7086 0.052 Uiso 1 1 calc R . . H1B H 0.0932 0.0511 0.8331 0.052 Uiso 1 1 calc R . . H1C H 0.1281 -0.0870 0.7206 0.052 Uiso 1 1 calc R . . C2 C 0.1965(2) 0.1628(2) 0.59803(19) 0.0288(3) Uani 1 1 d . . . C3 C 0.1279(2) 0.2951(2) 0.48099(19) 0.0289(3) Uani 1 1 d . . . H3 H -0.0039 0.3170 0.4725 0.035 Uiso 1 1 calc R . . C4 C 0.2642(2) 0.3989(2) 0.37212(18) 0.0268(3) Uani 1 1 d . . . C5 C 0.3951(2) 0.6006(2) 0.16986(19) 0.0278(3) Uani 1 1 d . . . C6 C 0.4176(2) 0.7403(2) 0.0339(2) 0.0343(4) Uani 1 1 d . . . H6 H 0.3121 0.8058 -0.0146 0.041 Uiso 1 1 calc R . . C7 C 0.6027(3) 0.7805(2) -0.0287(2) 0.0359(4) Uani 1 1 d . . . H7 H 0.6278 0.8764 -0.1219 0.043 Uiso 1 1 calc R . . C8 C 0.7505(2) 0.6787(2) 0.0468(2) 0.0333(4) Uani 1 1 d . . . C9 C 0.7295(2) 0.5402(2) 0.18417(19) 0.0302(3) Uani 1 1 d . . . H9 H 0.8353 0.4757 0.2330 0.036 Uiso 1 1 calc R . . C10 C 0.5437(2) 0.5005(2) 0.24719(18) 0.0268(3) Uani 1 1 d . . . C11 C 0.45457(19) 0.3696(2) 0.38054(18) 0.0260(3) Uani 1 1 d . . . C12 C 0.5251(2) 0.2316(2) 0.50731(18) 0.0263(3) Uani 1 1 d . . . O1 O 0.22218(15) 0.53800(15) 0.24680(13) 0.0306(3) Uani 1 1 d . . . O2 O 0.68609(14) 0.19147(16) 0.53548(14) 0.0331(3) Uani 1 1 d . . . O3 O 0.38580(14) 0.13126(15) 0.61206(13) 0.0287(3) Uani 1 1 d . . . F1 F 0.92931(15) 0.71943(16) -0.02002(14) 0.0460(3) Uani 1 1 d . . . 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 0.0263(7) 0.0370(9) 0.0356(8) -0.0006(7) 0.0035(6) -0.0102(6) C2 0.0201(6) 0.0332(8) 0.0317(8) -0.0068(6) 0.0021(5) -0.0073(5) C3 0.0193(6) 0.0333(8) 0.0318(8) -0.0049(6) 0.0006(5) -0.0061(5) C4 0.0230(7) 0.0285(8) 0.0262(7) -0.0035(6) -0.0001(5) -0.0048(5) C5 0.0258(7) 0.0292(8) 0.0269(7) -0.0054(6) 0.0009(5) -0.0060(5) C6 0.0367(8) 0.0329(8) 0.0307(8) -0.0041(7) -0.0020(6) -0.0049(7) C7 0.0443(9) 0.0305(8) 0.0294(8) -0.0030(6) 0.0034(7) -0.0119(7) C8 0.0305(8) 0.0353(9) 0.0322(8) -0.0072(7) 0.0073(6) -0.0143(6) C9 0.0265(7) 0.0317(8) 0.0312(8) -0.0063(6) 0.0028(6) -0.0106(6) C10 0.0257(7) 0.0277(7) 0.0258(7) -0.0061(6) 0.0024(5) -0.0072(5) C11 0.0202(6) 0.0284(7) 0.0280(7) -0.0059(6) 0.0022(5) -0.0064(5) C12 0.0204(6) 0.0289(8) 0.0289(8) -0.0073(6) 0.0021(5) -0.0068(5) O1 0.0233(5) 0.0331(6) 0.0303(6) -0.0002(4) -0.0007(4) -0.0038(4) O2 0.0209(5) 0.0373(6) 0.0379(6) -0.0048(5) -0.0026(4) -0.0032(4) O3 0.0206(5) 0.0312(6) 0.0307(6) -0.0020(4) 0.0008(4) -0.0068(4) F1 0.0365(6) 0.0489(7) 0.0453(6) -0.0012(5) 0.0110(4) -0.0212(5) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 C2 1.482(2) . ? C2 C3 1.345(2) . ? C2 O3 1.3676(18) . ? C3 C4 1.405(2) . ? C4 O1 1.3554(19) . ? C4 C11 1.365(2) . ? C5 C6 1.374(2) . ? C5 O1 1.3842(17) . ? C5 C10 1.392(2) . ? C6 C7 1.386(2) . ? C7 C8 1.386(3) . ? C8 F1 1.3534(17) . ? C8 C9 1.375(2) . ? C9 C10 1.3909(19) . ? C10 C11 1.436(2) . ? C11 C12 1.425(2) . ? C12 O2 1.2042(18) . ? C12 O3 1.3931(17) . ? 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 C3 C2 O3 122.60(13) . . ? C3 C2 C1 125.65(14) . . ? O3 C2 C1 111.74(14) . . ? C2 C3 C4 115.58(13) . . ? O1 C4 C11 112.43(13) . . ? O1 C4 C3 124.06(13) . . ? C11 C4 C3 123.51(15) . . ? C6 C5 O1 124.67(15) . . ? C6 C5 C10 124.53(15) . . ? O1 C5 C10 110.79(13) . . ? C5 C6 C7 116.34(17) . . ? C8 C7 C6 119.01(16) . . ? F1 C8 C9 117.61(16) . . ? F1 C8 C7 117.24(15) . . ? C9 C8 C7 125.15(15) . . ? C8 C9 C10 115.77(16) . . ? C9 C10 C5 119.19(14) . . ? C9 C10 C11 135.63(15) . . ? C5 C10 C11 105.16(13) . . ? C4 C11 C12 120.39(13) . . ? C4 C11 C10 106.14(14) . . ? C12 C11 C10 133.46(13) . . ? O2 C12 O3 116.68(14) . . ? O2 C12 C11 129.03(14) . . ? O3 C12 C11 114.30(12) . . ? C4 O1 C5 105.47(12) . . ? C2 O3 C12 123.58(13) . . ? _diffrn_measured_fraction_theta_max 0.983 _diffrn_reflns_theta_full 29.25 _diffrn_measured_fraction_theta_full 0.983 _refine_diff_density_max 0.314 _refine_diff_density_min -0.289 _refine_diff_density_rms 0.055 _database_code_depnum_ccdc_archive 'CCDC 945038'