# Supplementary Material (ESI) for ChemComm # This journal is © The Royal Society of Chemistry, 1999 # CCDC Number: 182/1297 data_CRYSTALS_cif _audit_creation_date 98-07-03 _audit_creation_method CRYSTALS # 1. SUBMISSION DETAILS _publ_contact_author ; Dr. Henri Rudler ; _publ_contact_author_phone ' 33 1 44 27 50 92 ' _publ_contact_author_fax ' 33 1 44 27 70 89 ' _publ_contact_author_email ' rudler@ccr.jussieu.fr ' _publ_requested_journal ' ? ' _publ_requested_coeditor_name ' ? ' _publ_contact_letter ; 2 compounds in manuscript 9/034741 ; #============================================================================= # 2. PROCESSING SUMMARY (IUCr Office Use Only) _journal_date_recd_electronic ? _journal_date_to_coeditor ? _journal_date_from_coeditor ? _journal_date_accepted ? _journal_date_printers_first ? _journal_date_printers_final ? _journal_date_proofs_out ? _journal_date_proofs_in ? _journal_coeditor_name ? _journal_coeditor_code ? _journal_coeditor_notes ; ? ; _journal_techeditor_code ? _journal_techeditor_notes ; ? ; _journal_coden_ASTM ? _journal_name_full ? _journal_year ? _journal_volume ? _journal_issue ? _journal_page_first ? _journal_page_last ? _journal_suppl_publ_number ? _journal_suppl_publ_pages ? #============================================================================= # 3. TITLE AND AUTHOR LIST _publ_section_title ; ? # Title of paper ; # The loop structure below should contain the names and addresses of all # authors, in the required order of publication. Repeat as necessary. loop_ _publ_author_name _publ_author_address 'Other, Anthony N.' #<--'Last name, first name' ; ? # Address ; 'Else, S. O.' ; ? # Address ; #============================================================================== # 4. TEXT _publ_section_abstract ; ? #Text of the abstract ; _publ_section_comment ; ? #Text of the paper ; _publ_section_exptl_prep ; ? ; _publ_section_exptl_refinement ; ? ; _publ_section_references ; # Add your own references - in alphabetic order Carruthers, J.R. and Watkin, D.J. (1979), (Chebychev Weighting) Acta Cryst, A35, 698-699 Sheldrick, G.M. (1986). SHELXS86. Program for the solution of crystal structures. Univ. of Gottingen, Federal Republic of Germany. Watkin, D.J., Prout, C.K. Carruthers, R.J. & Betteridge, P. (1996) CRYSTALS Issue 10. Chemical Crystallography Laboratory, OXFORD, UK. Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996) CAMERON, Chemical Crystallography Laboratory, OXFORD, UK. Watkin, D.J., Prout, C.K., Lilley, P.M.deQ. (1994), RC93, Chemical Crystallography Laboratory, Oxford, UK. ; _publ_section_figure_captions ; ? #Captions to figures ; _publ_section_acknowledgements ; ? ; #========================================================================== # Now, all the strucure specific goodies #========================================================================== _computing_data_collection 'CAD-4 software (Enraf-Nonius, 1989)' _computing_cell_refinement 'CAD-4 software (Enraf-Nonius, 1989)' _computing_data_reduction ; RC93 (Watkin, D.J., Prout, C.K., Lilley, P.M.deQ. 1994) ; _computing_structure_refinement ; CRYSTALS Issue 10 (Watkin, Prout, Carruthers & Betteridge, 1996) ; _computing_publication_material ; CRYSTALS Issue 10 (Watkin, Prout, Carruthers & Betteridge, 1996) ; _computing_molecular_graphics ; CAMERON (Watkin, Prout & Pearce, 1996) ; # _computing_structure_solution 'SHELXS86 (Sheldrick, 1986)' #========================================================================== # NOW THE GOODIES TO BE ENTERED BY HAND #========================================================================== _chemical_melting_point ? _diffrn_radiation_monochromator ' graphite ' _diffrn_measurement_device ' Enraf-nonius CAD4 ' _refine_ls_matrix_type ' full ' _refine_ls_weighting_scheme ; Chebychev polynomial (Carruthers & Watkin, 1979) ; _atom_sites_solution_primary ' Direct_Methods ' _atom_sites_solution_hydrogens ' Difference-Fourier map ' _refine_ls_hydrogen_treatment ; one overall isotropic thermal parameter refined ; #**************************************************************************** _chemical_name_systematic ; # IUPAC name, in full ? ; _cell_length_a 9.028(4) _cell_angle_alpha 90 _cell_length_b 8.436(8) _cell_angle_beta 99.328 _cell_length_c 24.179(8) _cell_angle_gamma 90 _cell_volume 1817(2) _symmetry_cell_setting 'Monoclinic ' _symmetry_space_group_name_H-M 'P 1 21/n 1 ' loop_ _symmetry_equiv_pos_as_xyz 'x,y,z' '-x,-y,-z' '-x+1/2,y+1/2,-z+1/2' 'x+1/2,-y+1/2,z+1/2' loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source 'C ' 0.0020 0.0020 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International_Tables_Vol_IV_Table_2.2B' 'H ' 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7997 0.0030 'International_Tables_Vol_IV_Table_2.2B' 'O ' 0.0080 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 'International_Tables_Vol_IV_Table_2.2B' 'N ' 0.0040 0.0030 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 'International_Tables_Vol_IV_Table_2.2B' _chemical_formula_sum ' C22 H24 O2 ' _chemical_formula_moiety ' C22 H24 O2 ' _chemical_compound_source ; ? ; _chemical_formula_weight 320.43 _cell_measurement_reflns_used 25 _cell_measurement_theta_min 10.7 _cell_measurement_theta_max 11.3 _cell_measurement_temperature 295K _cell_formula_units_Z 4 _exptl_crystal_description ' prism ' _exptl_crystal_colour ' none ' _exptl_crystal_size_min 0.22 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_max 0.53 _exptl_crystal_density_diffrn 1.17 _exptl_crystal_density_meas ? _exptl_crystal_F_000 688.16 _exptl_absorpt_coefficient_mu 0.07 _exptl_absorpt_correction_type ' none ' _diffrn_standards_interval_time ? _diffrn_standards_interval_count ? _diffrn_standards_number 2 _diffrn_standards_decay_% ' none' _diffrn_ambient_temperature 295K _diffrn_reflns_number 3663 _reflns_number_total 3193 _diffrn_reflns_av_R_equivalents 0.05 _reflns_number_observed 1319 _diffrn_reflns_theta_min 1 _diffrn_reflns_theta_max 25 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 28 _reflns_limit_h_min -10 _reflns_limit_h_max 10 _reflns_limit_k_min 0 _reflns_limit_k_max 10 _reflns_limit_l_min 0 _reflns_limit_l_max 28 _reflns_observed_criterion >3.00\s(I) _refine_diff_density_min -0.19 _refine_diff_density_max 0.18 _refine_ls_number_reflns 1319 _refine_ls_number_parameters 219 _refine_ls_R_factor_obs 0.0544 _refine_ls_wR_factor_obs 0.0645 _refine_ls_goodness_of_fit_obs 1.1501 _refine_ls_shift/esd_max 0.103004 _refine_ls_structure_factor_coef F _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71069 _diffrn_measurement_method 2\q/\w loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_occupancy _atom_site_thermal_displace_type O1 0.3815(3) 0.0994(3) 0.8999(1) 0.0723 1.0000 Uani O2 0.0456(3) -0.0170(3) 0.8892(1) 0.0644 1.0000 Uani C1 0.3012(4) 0.0312(4) 0.9279(2) 0.0562 1.0000 Uani C2 0.1892(4) -0.0913(5) 0.9008(1) 0.0583 1.0000 Uani C3 0.1756(4) -0.2316(4) 0.9385(2) 0.0574 1.0000 Uani C4 0.1374(4) -0.1734(5) 0.9935(2) 0.0625 1.0000 Uani C5 0.2528(4) -0.0573(4) 1.0245(1) 0.0599 1.0000 Uani C6 0.3025(4) 0.0686(4) 0.9876(2) 0.0576 1.0000 Uani C7 0.0344(6) 0.0845(7) 0.8411(2) 0.1008 1.0000 Uani C8 -0.1172(7) 0.1552(8) 0.8306(2) 0.1146 1.0000 Uani C9 0.0621(5) -0.3544(5) 0.9099(2) 0.0707 1.0000 Uani C10 0.3495(4) 0.2149(5) 1.0040(2) 0.0621 1.0000 Uani C11 0.3655(4) 0.2905(4) 1.0587(2) 0.0573 1.0000 Uani C12 0.3890(4) 0.2152(5) 1.1106(2) 0.0638 1.0000 Uani C13 0.4003(5) 0.2983(5) 1.1593(2) 0.0777 1.0000 Uani C14 0.3913(5) 0.4603(6) 1.1585(2) 0.0825 1.0000 Uani C15 0.3737(6) 0.5387(5) 1.1092(2) 0.0838 1.0000 Uani C16 0.3628(5) 0.4590(5) 1.0593(2) 0.0761 1.0000 Uani C21 0.0855(4) -0.4073(5) 0.8536(2) 0.0611 1.0000 Uani C22 0.1997(5) -0.5087(5) 0.8468(2) 0.0841 1.0000 Uani C23 0.2241(7) -0.5556(7) 0.7940(3) 0.1016 1.0000 Uani C24 0.1357(8) -0.4987(9) 0.7477(3) 0.0976 1.0000 Uani C25 0.0226(8) -0.4008(8) 0.7532(2) 0.0998 1.0000 Uani C26 -0.0030(5) -0.3533(6) 0.8056(2) 0.0873 1.0000 Uani H21 0.2300 -0.1254 0.8653 0.103(3) 1.0000 Uiso H31 0.2786 -0.2800 0.9490 0.103(3) 1.0000 Uiso H41 0.1304 -0.2568 1.0175 0.103(3) 1.0000 Uiso H42 0.0400 -0.1221 0.9859 0.103(3) 1.0000 Uiso H51 0.3439 -0.1157 1.0411 0.103(3) 1.0000 Uiso H52 0.2143 -0.0025 1.0585 0.103(3) 1.0000 Uiso H71 0.0564 0.1593 0.8626 0.103(3) 1.0000 Uiso H72 0.0321 0.0307 0.8119 0.103(3) 1.0000 Uiso H81 -0.0918 0.2046 0.8638 0.103(3) 1.0000 Uiso H82 -0.1632 0.0743 0.8176 0.103(3) 1.0000 Uiso H83 -0.1286 0.2332 0.7978 0.103(3) 1.0000 Uiso H91 -0.0371 -0.3118 0.9114 0.103(3) 1.0000 Uiso H92 0.0343 -0.4179 0.9323 0.103(3) 1.0000 Uiso H101 0.3879 0.2800 0.9751 0.103(3) 1.0000 Uiso H121 0.3732 0.0989 1.1086 0.103(3) 1.0000 Uiso H131 0.4164 0.2332 1.1915 0.103(3) 1.0000 Uiso H141 0.4079 0.5089 1.2035 0.103(3) 1.0000 Uiso H151 0.3868 0.6711 1.1116 0.103(3) 1.0000 Uiso H161 0.3654 0.5182 1.0218 0.103(3) 1.0000 Uiso H221 0.2664 -0.5371 0.8791 0.103(3) 1.0000 Uiso H231 0.3146 -0.6393 0.7925 0.103(3) 1.0000 Uiso H241 0.1729 -0.5707 0.7094 0.103(3) 1.0000 Uiso H251 -0.0504 -0.3496 0.7319 0.103(3) 1.0000 Uiso H261 -0.0900 -0.2914 0.8084 0.103(3) 1.0000 Uiso loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.075(2) 0.076(2) 0.071(2) 0.003(1) 0.017(1) -0.011(2) O2 0.064(2) 0.072(2) 0.059(2) 0.011(1) 0.005(1) 0.003(1) C1 0.055(2) 0.057(2) 0.059(2) 0.006(2) 0.013(2) 0.010(2) C2 0.050(2) 0.065(2) 0.061(2) 0.001(2) 0.007(2) 0.002(2) C3 0.051(2) 0.057(2) 0.065(2) 0.001(2) 0.011(2) 0.004(2) C4 0.066(3) 0.067(2) 0.058(2) 0.009(2) 0.015(2) 0.003(2) C5 0.065(2) 0.061(2) 0.054(2) 0.006(2) 0.005(2) 0.005(2) C6 0.054(2) 0.058(2) 0.060(2) 0.001(2) 0.006(2) 0.005(2) C7 0.107(4) 0.109(4) 0.091(4) 0.022(3) -0.001(3) 0.012(3) C8 0.117(5) 0.145(5) 0.104(4) 0.041(4) -0.009(3) 0.027(4) C9 0.068(3) 0.074(3) 0.082(3) -0.006(2) 0.029(2) -0.010(2) C10 0.061(2) 0.064(2) 0.062(2) 0.003(2) 0.012(2) 0.005(2) C11 0.055(2) 0.056(2) 0.061(2) -0.005(2) 0.008(2) 0.005(2) C12 0.068(3) 0.062(2) 0.061(3) -0.001(2) 0.004(2) 0.007(2) C13 0.092(3) 0.076(3) 0.066(3) 0.001(2) 0.003(2) 0.006(2) C14 0.098(4) 0.077(3) 0.076(3) -0.016(3) 0.009(2) 0.000(3) C15 0.120(4) 0.061(3) 0.083(3) -0.013(3) 0.014(3) 0.006(2) C16 0.095(3) 0.063(3) 0.075(3) -0.001(2) 0.014(2) 0.008(2) C21 0.065(2) 0.055(2) 0.069(3) -0.009(2) 0.016(2) -0.012(2) C22 0.085(3) 0.077(3) 0.099(4) -0.016(3) 0.019(3) 0.010(3) C23 0.093(4) 0.113(4) 0.132(5) -0.046(4) 0.041(4) -0.004(3) C24 0.096(4) 0.148(6) 0.107(5) -0.052(4) 0.044(4) -0.055(4) C25 0.114(5) 0.139(5) 0.074(4) -0.000(3) -0.006(3) -0.052(4) C26 0.075(3) 0.092(3) 0.095(4) -0.010(3) -0.003(3) -0.006(3) _refine_ls_extinction_coef ' none ' loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag O1 . C1 . 1.214(4) yes O2 . C2 . 1.426(4) yes O2 . C7 . 1.433(6) yes C1 . C2 . 1.518(5) yes C1 . C6 . 1.478(5) yes C2 . C3 . 1.511(5) yes C2 . H21 . 1.030(4) no C3 . C4 . 1.510(5) yes C3 . C9 . 1.539(6) yes C3 . H31 . 1.009(3) no C4 . C5 . 1.534(6) yes C4 . H41 . 0.921(4) no C4 . H42 . 0.971(4) no C5 . C6 . 1.502(5) yes C5 . H51 . 0.987(4) no C5 . H52 . 1.050(4) no C6 . C10 . 1.343(5) yes C7 . C8 . 1.476(8) yes C7 . H71 . 0.821(6) no C7 . H72 . 0.838(6) no C8 . H81 . 0.900(6) no C8 . H82 . 0.833(7) no C8 . H83 . 1.024(5) no C9 . C21 . 1.480(5) yes C9 . H91 . 0.972(4) no C9 . H92 . 0.828(4) no C10 . C11 . 1.454(5) yes C10 . H101 . 0.994(4) no C11 . C12 . 1.391(5) yes C11 . C16 . 1.422(6) yes C12 . C13 . 1.360(6) yes C12 . H121 . 0.991(4) no C13 . C14 . 1.369(6) yes C13 . H131 . 0.945(4) no C14 . C15 . 1.350(6) yes C14 . H141 . 1.150(4) no C15 . C16 . 1.370(6) yes C15 . H151 . 1.124(4) no C16 . H161 . 1.040(4) no C21 . C22 . 1.370(6) yes C21 . C26 . 1.375(6) yes C22 . C23 . 1.388(7) yes C22 . H221 . 0.938(5) no C23 . C24 . 1.352(9) yes C23 . H231 . 1.085(6) no C24 . C25 . 1.337(9) yes C24 . H241 . 1.200(6) no C25 . C26 . 1.385(7) yes C25 . H251 . 0.880(7) no C26 . H261 . 0.954(5) no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C2 . O2 . C7 . 111.4(3) no O1 . C1 . C2 . 119.9(3) no O1 . C1 . C6 . 122.2(3) no C2 . C1 . C6 . 117.8(3) no O2 . C2 . C1 . 107.8(3) no O2 . C2 . C3 . 107.7(3) no C1 . C2 . C3 . 112.8(3) no O2 . C2 . H21 . 113.3(3) no C1 . C2 . H21 . 104.3(3) no C3 . C2 . H21 . 111.1(3) no C2 . C3 . C4 . 109.2(3) no C2 . C3 . C9 . 111.7(3) no C4 . C3 . C9 . 112.6(3) no C2 . C3 . H31 . 107.9(3) no C4 . C3 . H31 . 104.0(3) no C9 . C3 . H31 . 111.1(3) no C3 . C4 . C5 . 113.9(3) no C3 . C4 . H41 . 110.8(3) no C5 . C4 . H41 . 106.9(3) no C3 . C4 . H42 . 107.9(3) no C5 . C4 . H42 . 109.4(3) no H41 . C4 . H42 . 107.8(4) no C4 . C5 . C6 . 114.0(3) no C4 . C5 . H51 . 109.6(3) no C6 . C5 . H51 . 106.6(3) no C4 . C5 . H52 . 112.3(3) no C6 . C5 . H52 . 108.8(3) no H51 . C5 . H52 . 105.1(3) no C1 . C6 . C5 . 118.3(3) no C1 . C6 . C10 . 115.9(3) no C5 . C6 . C10 . 125.8(3) no O2 . C7 . C8 . 108.8(4) no O2 . C7 . H71 . 88.2(4) no C8 . C7 . H71 . 85.5(5) no O2 . C7 . H72 . 110.4(5) no C8 . C7 . H72 . 100.2(5) no H71 . C7 . H72 . 157.1(8) no C7 . C8 . H81 . 86.5(5) no C7 . C8 . H82 . 97.3(6) no H81 . C8 . H82 . 139.0(7) no C7 . C8 . H83 . 111.5(6) no H81 . C8 . H83 . 111.8(7) no H82 . C8 . H83 . 104.6(6) no C3 . C9 . C21 . 115.6(3) no C3 . C9 . H91 . 106.6(3) no C21 . C9 . H91 . 114.5(4) no C3 . C9 . H92 . 113.2(4) no C21 . C9 . H92 . 120.6(4) no H91 . C9 . H92 . 80.6(3) no C6 . C10 . C11 . 130.6(4) no C6 . C10 . H101 . 115.5(4) no C11 . C10 . H101 . 113.7(4) no C10 . C11 . C12 . 126.7(3) no C10 . C11 . C16 . 116.7(4) no C12 . C11 . C16 . 116.6(4) no C11 . C12 . C13 . 121.6(4) no C11 . C12 . H121 . 114.2(4) no C13 . C12 . H121 . 122.8(4) no C12 . C13 . C14 . 120.5(4) no C12 . C13 . H131 . 113.2(4) no C14 . C13 . H131 . 126.3(5) no C13 . C14 . C15 . 119.9(4) no C13 . C14 . H141 . 110.2(4) no C15 . C14 . H141 . 129.8(4) no C14 . C15 . C16 . 121.2(4) no C14 . C15 . H151 . 116.4(4) no C16 . C15 . H151 . 121.7(5) no C11 . C16 . C15 . 120.1(4) no C11 . C16 . H161 . 117.9(4) no C15 . C16 . H161 . 121.6(4) no C9 . C21 . C22 . 121.4(4) no C9 . C21 . C26 . 121.7(4) no C22 . C21 . C26 . 116.8(4) no C21 . C22 . C23 . 121.6(5) no C21 . C22 . H221 . 117.0(5) no C23 . C22 . H221 . 121.2(5) no C22 . C23 . C24 . 119.9(5) no C22 . C23 . H231 . 116.6(7) no C24 . C23 . H231 . 123.4(6) no C23 . C24 . C25 . 119.7(5) no C23 . C24 . H241 . 104.9(7) no C25 . C24 . H241 . 134.6(8) no C24 . C25 . C26 . 120.8(6) no C24 . C25 . H251 . 139.1(8) no C26 . C25 . H251 . 100.0(8) no C21 . C26 . C25 . 121.1(5) no C21 . C26 . H261 . 119.7(5) no C25 . C26 . H261 . 118.9(6) no #===END data_2 _chemical_melting_point ? _diffrn_radiation_monochromator ' graphite' _diffrn_measurement_device ' Enraf-nonius CAD4 ' _refine_ls_matrix_type ' full ' _refine_ls_weighting_scheme ; Chebychev polynomial (Carruthers & Watkin, 1979) ; _atom_sites_solution_primary ' Direct_Methods ' _atom_sites_solution_hydrogens ' Difference Fourier map ' _refine_ls_hydrogen_treatment ; one overall isotropic thermal parameter refined ; #**************************************************************************** _chemical_name_systematic ; # IUPAC name, in full ? ; _cell_length_a 11.198(5) _cell_angle_alpha 90 _cell_length_b 6.867(1) _cell_angle_beta 90.26(7) _cell_length_c 12.192(18) _cell_angle_gamma 90 _cell_volume 937(1) _symmetry_cell_setting 'Monoclinic ' _symmetry_space_group_name_H-M 'P 1 c 1 ' loop_ _symmetry_equiv_pos_as_xyz 'x,y,z' 'x,-y,z+1/2' loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source 'C ' 0.0020 0.0020 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International_Tables_Vol_IV_Table_2.2B' 'H ' 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7997 0.0030 'International_Tables_Vol_IV_Table_2.2B' 'O ' 0.0080 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 'International_Tables_Vol_IV_Table_2.2B' _chemical_formula_sum ' C23 H24 O3 ' _chemical_formula_moiety ' C23 H24 O3 ' _chemical_compound_source ; ? ; _chemical_formula_weight 348.44 _cell_measurement_reflns_used 25 _cell_measurement_theta_min 13 _cell_measurement_theta_max 13.5 _cell_measurement_temperature 298K _cell_formula_units_Z 2 _exptl_crystal_description ' plate ' _exptl_crystal_colour ' colourless ' _exptl_crystal_size_min 0.1 _exptl_crystal_size_mid 0.4 _exptl_crystal_size_max 0.7 _exptl_crystal_density_diffrn 1.23 _exptl_crystal_density_meas ? _exptl_crystal_F_000 372.10 _exptl_absorpt_coefficient_mu 0.08 _exptl_absorpt_correction_type 'none' _diffrn_standards_interval_time 3600s _diffrn_standards_number 2 _diffrn_standards_decay_% 'none' _diffrn_ambient_temperature 295K _diffrn_reflns_number 3075 _reflns_number_total 2728 _diffrn_reflns_av_R_equivalents 0.04 _reflns_number_observed 1806 _diffrn_reflns_theta_min 1 _diffrn_reflns_theta_max 30 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _reflns_limit_h_min -15 _reflns_limit_h_max 15 _reflns_limit_k_min 0 _reflns_limit_k_max 9 _reflns_limit_l_min 0 _reflns_limit_l_max 17 _reflns_observed_criterion >3.00\s(I) _refine_diff_density_min -0.24 _refine_diff_density_max 0.29 _refine_ls_number_reflns 1806 _refine_ls_number_parameters 237 _refine_ls_R_factor_obs 0.0511 _refine_ls_wR_factor_obs 0.0643 _refine_ls_goodness_of_fit_obs 1.0758 _refine_ls_shift/esd_max 0.087555 _refine_ls_structure_factor_coef F _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71069 _diffrn_measurement_method 2\q/\w loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_occupancy _atom_site_thermal_displace_type O1 0.5286(2) 0.1316(3) 0.9347(2) 0.0417 1.0000 Uani O2 0.6514(2) 0.0050(3) 1.0602(3) 0.0524 1.0000 Uani O3 0.3126(2) 0.2122(3) 0.7935(2) 0.0373 1.0000 Uani C2 0.5945(3) 0.1405(4) 1.0296(3) 0.0397 1.0000 Uani C3 0.5777(2) 0.3351(4) 1.0794(2) 0.0346 1.0000 Uani C4 0.4415(3) 0.6261(4) 1.0288(3) 0.0402 1.0000 Uani C5 0.3075(3) 0.5977(4) 1.0097(2) 0.0402 1.0000 Uani C6 0.2800(3) 0.4978(4) 0.9008(2) 0.0384 1.0000 Uani C7 0.3374(2) 0.2950(4) 0.8977(2) 0.0314 1.0000 Uani C8 0.1456(3) 0.4895(6) 0.8760(3) 0.0476 1.0000 Uani C9 0.3221(4) 0.0069(5) 0.7897(3) 0.0475 1.0000 Uani C10 0.2809(5) -0.0652(6) 0.6813(3) 0.0566 1.0000 Uani C30 0.5018(2) 0.4345(4) 1.0157(2) 0.0331 1.0000 Uani C31 0.6413(2) 0.3959(4) 1.1798(2) 0.0355 1.0000 Uani C32 0.6598(3) 0.2675(5) 1.2655(3) 0.0443 1.0000 Uani C33 0.7221(3) 0.3268(7) 1.3577(3) 0.0482 1.0000 Uani C34 0.7665(3) 0.5135(7) 1.3657(3) 0.0521 1.0000 Uani C35 0.7494(3) 0.6425(6) 1.2800(3) 0.0498 1.0000 Uani C36 0.6867(3) 0.5840(5) 1.1871(3) 0.0413 1.0000 Uani C70 0.4711(3) 0.3166(4) 0.9166(2) 0.0354 1.0000 Uani C81 0.0728(3) 0.3585(6) 0.9495(3) 0.0511 1.0000 Uani C82 0.0425(4) 0.1716(8) 0.9182(5) 0.0726 1.0000 Uani C83 -0.0249(5) 0.055(1) 0.9872(7) 0.0923 1.0000 Uani C84 -0.0633(4) 0.119(1) 1.0849(6) 0.0912 1.0000 Uani C85 -0.0335(4) 0.303(1) 1.1183(5) 0.0859 1.0000 Uani C86 0.0325(3) 0.4208(9) 1.0522(4) 0.0658 1.0000 Uani H41 0.4851 0.7006 0.9790 0.072(3) 1.0000 Uiso H42 0.4626 0.6886 1.0968 0.072(3) 1.0000 Uiso H51 0.2691 0.7335 1.0056 0.072(3) 1.0000 Uiso H52 0.2624 0.5313 1.0660 0.072(3) 1.0000 Uiso H61 0.3293 0.5712 0.8409 0.072(3) 1.0000 Uiso H71 0.3006 0.2147 0.9513 0.072(3) 1.0000 Uiso H81 0.1399 0.4509 0.8041 0.072(3) 1.0000 Uiso H82 0.1153 0.6151 0.8792 0.072(3) 1.0000 Uiso H91 0.2920 -0.0624 0.8521 0.072(3) 1.0000 Uiso H92 0.4070 -0.0203 0.7896 0.072(3) 1.0000 Uiso H101 0.2055 -0.0102 0.6657 0.072(3) 1.0000 Uiso H102 0.3121 -0.0153 0.6212 0.072(3) 1.0000 Uiso H103 0.2692 -0.2081 0.6777 0.072(3) 1.0000 Uiso H321 0.6357 0.1352 1.2593 0.072(3) 1.0000 Uiso H331 0.7356 0.2116 1.4249 0.072(3) 1.0000 Uiso H341 0.8075 0.5615 1.4294 0.072(3) 1.0000 Uiso H351 0.7735 0.7752 1.2800 0.072(3) 1.0000 Uiso H361 0.6768 0.6718 1.1158 0.072(3) 1.0000 Uiso H710 0.5068 0.3680 0.8495 0.072(3) 1.0000 Uiso H821 0.0570 0.1410 0.8347 0.072(3) 1.0000 Uiso H831 -0.0492 -0.0638 0.9490 0.072(3) 1.0000 Uiso H841 -0.1265 0.0518 1.1203 0.072(3) 1.0000 Uiso H851 -0.0779 0.3632 1.1900 0.072(3) 1.0000 Uiso H861 0.0601 0.5508 1.0556 0.072(3) 1.0000 Uiso 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 0.050(1) 0.035(1) 0.048(1) -0.0115(9) -0.0116(9) 0.0030(9) O2 0.064(2) 0.035(1) 0.076(2) -0.003(1) -0.023(1) 0.008(1) O3 0.058(1) 0.037(1) 0.0265(9) -0.0021(8) -0.0112(8) -0.0019(9) C2 0.044(1) 0.036(1) 0.042(1) -0.006(1) -0.008(1) -0.001(1) C3 0.039(1) 0.033(1) 0.032(1) 0.001(1) -0.003(1) -0.001(1) C4 0.055(2) 0.032(1) 0.041(1) -0.005(1) -0.014(1) 0.003(1) C5 0.051(2) 0.037(1) 0.038(1) -0.000(1) -0.010(1) 0.007(1) C6 0.052(2) 0.037(1) 0.032(1) 0.002(1) -0.010(1) 0.006(1) C7 0.047(1) 0.031(1) 0.023(1) -0.000(1) -0.0079(9) 0.001(1) C8 0.051(2) 0.057(2) 0.047(2) 0.000(1) -0.020(1) 0.012(1) C9 0.091(3) 0.036(1) 0.042(2) -0.009(1) -0.026(2) 0.001(2) C10 0.112(3) 0.043(2) 0.048(2) -0.011(2) -0.026(2) -0.006(2) C30 0.039(1) 0.031(1) 0.031(1) -0.001(1) -0.0043(9) -0.004(1) C31 0.037(1) 0.041(1) 0.030(1) -0.001(1) -0.0031(9) 0.001(1) C32 0.046(1) 0.048(2) 0.041(2) 0.007(1) -0.005(1) 0.003(1) C33 0.047(2) 0.088(3) 0.031(1) 0.010(2) -0.009(1) 0.007(2) C34 0.045(2) 0.093(3) 0.037(2) -0.008(2) -0.010(1) -0.001(2) C35 0.049(2) 0.060(2) 0.052(2) -0.013(2) -0.012(1) -0.012(2) C36 0.045(1) 0.043(2) 0.038(1) -0.000(1) -0.008(1) -0.005(1) C70 0.045(1) 0.034(1) 0.030(1) -0.002(1) -0.002(1) -0.000(1) C81 0.035(1) 0.073(2) 0.059(2) -0.005(2) -0.015(1) 0.009(2) C82 0.050(2) 0.077(3) 0.101(4) -0.009(3) -0.005(2) 0.001(2) C83 0.059(3) 0.088(4) 0.159(7) 0.000(4) -0.009(4) -0.014(3) C84 0.045(2) 0.164(7) 0.116(5) 0.032(5) 0.011(3) -0.013(3) C85 0.050(2) 0.164(6) 0.079(3) 0.013(4) -0.000(2) -0.001(3) C86 0.050(2) 0.101(4) 0.062(2) 0.000(2) -0.014(2) 0.010(2) _refine_ls_extinction_coef 53.4 _refine_ls_extinction_method 'Larson 1970 Crystallographic Computing eq 22' loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag O1 . C2 . 1.371(4) yes O1 . C70 . 1.441(4) yes O2 . C2 . 1.187(4) yes O3 . C7 . 1.418(3) yes O3 . C9 . 1.415(4) yes C2 . C3 . 1.480(4) yes C3 . C30 . 1.336(4) yes C3 . C31 . 1.473(4) yes C4 . C5 . 1.529(4) yes C4 . C30 . 1.488(4) yes C4 . H41 . 0.934(3) no C4 . H42 . 0.963(3) no C5 . C6 . 1.525(4) yes C5 . H51 . 1.028(3) no C5 . H52 . 0.968(3) no C6 . C7 . 1.535(4) yes C6 . C8 . 1.535(5) yes C6 . H61 . 1.046(3) no C7 . C70 . 1.520(4) yes C7 . H71 . 0.951(3) no C8 . C81 . 1.511(6) yes C8 . H81 . 0.918(4) no C8 . H82 . 0.928(4) no C9 . C10 . 1.483(5) yes C9 . H91 . 0.960(4) no C9 . H92 . 0.968(5) no C10 . H101 . 0.943(5) no C10 . H102 . 0.882(5) no C10 . H103 . 0.991(4) no C30 . C70 . 1.493(4) yes C31 . C32 . 1.383(4) yes C31 . C36 . 1.391(4) yes C32 . C33 . 1.382(5) yes C32 . H321 . 0.950(3) no C33 . C34 . 1.378(6) yes C33 . H331 . 1.148(4) no C34 . C35 . 1.383(6) yes C34 . H341 . 0.959(3) no C35 . C36 . 1.389(4) yes C35 . H351 . 0.951(4) no C36 . H361 . 1.063(3) no C70 . H710 . 0.978(3) no C81 . C82 . 1.381(6) yes C81 . C86 . 1.400(6) yes C82 . C83 . 1.387(9) yes C82 . H821 . 1.053(6) no C83 . C84 . 1.34(1) yes C83 . H831 . 0.978(7) no C84 . C85 . 1.37(1) yes C84 . H841 . 0.950(6) no C85 . C86 . 1.362(9) yes C85 . H851 . 1.089(7) no C86 . H861 . 0.945(6) no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C2 . O1 . C70 . 109.2(2) no C7 . O3 . C9 . 114.5(2) no O1 . C2 . O2 . 121.1(3) no O1 . C2 . C3 . 108.5(2) no O2 . C2 . C3 . 130.4(3) no C2 . C3 . C30 . 107.7(2) no C2 . C3 . C31 . 122.3(2) no C30 . C3 . C31 . 129.9(3) no C5 . C4 . C30 . 108.4(2) no C5 . C4 . H41 . 119.2(3) no C30 . C4 . H41 . 100.1(3) no C5 . C4 . H42 . 115.1(3) no C30 . C4 . H42 . 112.1(3) no H41 . C4 . H42 . 100.9(3) no C4 . C5 . C6 . 112.5(3) no C4 . C5 . H51 . 107.5(3) no C6 . C5 . H51 . 106.4(2) no C4 . C5 . H52 . 117.9(3) no C6 . C5 . H52 . 107.5(3) no H51 . C5 . H52 . 104.0(3) no C5 . C6 . C7 . 110.3(2) no C5 . C6 . C8 . 112.4(3) no C7 . C6 . C8 . 111.8(2) no C5 . C6 . H61 . 106.6(3) no C7 . C6 . H61 . 101.4(2) no C8 . C6 . H61 . 113.7(3) no O3 . C7 . C6 . 107.8(2) no O3 . C7 . C70 . 111.4(2) no C6 . C7 . C70 . 108.6(2) no O3 . C7 . H71 . 107.4(2) no C6 . C7 . H71 . 109.0(2) no C70 . C7 . H71 . 112.4(2) no C6 . C8 . C81 . 115.9(3) no C6 . C8 . H81 . 105.2(3) no C81 . C8 . H81 . 111.0(4) no C6 . C8 . H82 . 108.4(3) no C81 . C8 . H82 . 109.3(4) no H81 . C8 . H82 . 106.5(3) no O3 . C9 . C10 . 109.8(3) no O3 . C9 . H91 . 116.2(3) no C10 . C9 . H91 . 115.6(4) no O3 . C9 . H92 . 105.5(3) no C10 . C9 . H92 . 103.7(4) no H91 . C9 . H92 . 104.7(3) no C9 . C10 . H101 . 108.7(4) no C9 . C10 . H102 . 119.1(4) no H101 . C10 . H102 . 92.0(4) no C9 . C10 . H103 . 114.2(4) no H101 . C10 . H103 . 105.7(4) no H102 . C10 . H103 . 113.6(4) no C3 . C30 . C4 . 132.6(3) no C3 . C30 . C70 . 109.7(2) no C4 . C30 . C70 . 117.6(2) no C3 . C31 . C32 . 121.2(3) no C3 . C31 . C36 . 119.5(2) no C32 . C31 . C36 . 119.4(3) no C31 . C32 . C33 . 120.0(3) no C31 . C32 . H321 . 120.5(3) no C33 . C32 . H321 . 119.3(3) no C32 . C33 . C34 . 120.8(3) no C32 . C33 . H331 . 116.2(4) no C34 . C33 . H331 . 123.0(3) no C33 . C34 . C35 . 119.6(3) no C33 . C34 . H341 . 123.2(4) no C35 . C34 . H341 . 117.1(4) no C34 . C35 . C36 . 119.9(3) no C34 . C35 . H351 . 125.2(3) no C36 . C35 . H351 . 114.8(4) no C31 . C36 . C35 . 120.3(3) no C31 . C36 . H361 . 115.9(3) no C35 . C36 . H361 . 123.6(3) no O1 . C70 . C7 . 112.1(2) no O1 . C70 . C30 . 104.7(2) no C7 . C70 . C30 . 113.5(2) no O1 . C70 . H710 . 105.1(2) no C7 . C70 . H710 . 108.3(2) no C30 . C70 . H710 . 112.8(3) no C8 . C81 . C82 . 121.5(4) no C8 . C81 . C86 . 121.6(4) no C82 . C81 . C86 . 116.9(5) no C81 . C82 . C83 . 120.2(6) no C81 . C82 . H821 . 114.5(5) no C83 . C82 . H821 . 123.9(5) no C82 . C83 . C84 . 121.9(6) no C82 . C83 . H831 . 110.1(8) no C84 . C83 . H831 . 127.3(7) no C83 . C84 . C85 . 119.1(6) no C83 . C84 . H841 . 119.2(9) no C85 . C84 . H841 . 119.5(8) no C84 . C85 . C86 . 120.3(6) no C84 . C85 . H851 . 118.5(6) no C86 . C85 . H851 . 120.1(8) no C81 . C86 . C85 . 121.7(6) no C81 . C86 . H861 . 102.8(4) no C85 . C86 . H861 . 135.4(6) no