data_global _journal_coden_Cambridge 177 _journal_volume ? _journal_year ? _journal_page_first ? _publ_requested_journal 'Organic & Biomolecular Chemistry' loop_ _publ_author_name 'Herwig Schottenberger' 'Ulrike Erika Ida Horvath' 'Gerhard Laus' 'Karl-Hans Ongania' 'Johannes Schutz' ; A.Schwarzler ; 'Klaus Wurst' _publ_contact_author_name 'Prof Herwig Schottenberger' _publ_contact_author_address ; Prof Herwig Schottenberger Dept. of General, Inorganic and Theoretical Chemistry University of Innsbruck Innrain 52a Innsbruck Tyrol 6020 AUSTRIA ; _publ_contact_author_email HERWIG.SCHOTTENBERGER@UIBK.AC.AT _publ_section_title ; Solvatochromism, halochromism and preferential solvation of new dipolar guaiazulenyl 1,4-benzoquinone methides ; data_kor _database_code_CSD 195492 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H23 B F4 O' _chemical_formula_weight 390.21 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' B B 0.0013 0.0007 '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 monoclinic _symmetry_space_group_name_H-M P2(1)/m loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' '-x, -y, -z' 'x, -y-1/2, z' _cell_length_a 9.8532(7) _cell_length_b 6.9944(5) _cell_length_c 14.504(1) _cell_angle_alpha 90.00 _cell_angle_beta 105.737(3) _cell_angle_gamma 90.00 _cell_volume 962.11(12) _cell_formula_units_Z 2 _cell_measurement_temperature 233(2) _cell_measurement_reflns_used 6066 _cell_measurement_theta_min 1.0 _cell_measurement_theta_max 22.5 _exptl_crystal_description plate _exptl_crystal_colour red _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.347 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 408 _exptl_absorpt_coefficient_mu 0.107 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 233(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 'Kappa CCD' _diffrn_measurement_method 'phi- and omega-scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 4286 _diffrn_reflns_av_R_equivalents 0.0427 _diffrn_reflns_av_sigmaI/netI 0.0362 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.46 _diffrn_reflns_theta_max 21.48 _reflns_number_total 1215 _reflns_number_gt 945 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Kappa CCD' _computing_cell_refinement ? _computing_data_reduction 'DENZO and SCALEPACK' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0497P)^2^+0.4065P] 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; refined at O1' _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.024(6) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1215 _refine_ls_number_parameters 169 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0595 _refine_ls_R_factor_gt 0.0423 _refine_ls_wR_factor_ref 0.1070 _refine_ls_wR_factor_gt 0.0995 _refine_ls_goodness_of_fit_ref 1.048 _refine_ls_restrained_S_all 1.048 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.9230(3) 0.2500 0.31279(18) 0.0572(8) Uani 1 2 d S . . H1O H 0.829(5) 0.2500 0.314(3) 0.081(15) Uiso 1 2 d S . . C1 C 0.9407(4) 0.2500 0.2229(3) 0.0424(10) Uani 1 2 d S . . C2 C 0.8296(4) 0.2500 0.1421(3) 0.0501(11) Uani 1 2 d S . . H2 H 0.7365 0.2500 0.1472 0.060 Uiso 1 2 calc S . . C3 C 0.8551(4) 0.2500 0.0534(3) 0.0512(11) Uani 1 2 d S . . H3 H 0.7776 0.2500 -0.0012 0.061 Uiso 1 2 calc S . . C4 C 0.9899(4) 0.2500 0.0407(3) 0.0416(10) Uani 1 2 d S . . C5 C 1.1011(4) 0.2500 0.1242(3) 0.0464(10) Uani 1 2 d S . . H5 H 1.1943 0.2500 0.1193 0.056 Uiso 1 2 calc S . . C6 C 1.0777(4) 0.2500 0.2135(3) 0.0487(11) Uani 1 2 d S . . H6 H 1.1547 0.2500 0.2685 0.058 Uiso 1 2 calc S . . C7 C 0.9983(4) 0.2500 -0.0570(3) 0.0448(10) Uani 1 2 d S . . H7 H 0.9096 0.2500 -0.1023 0.054 Uiso 1 2 calc S . . C1' C 1.3371(4) 0.2500 -0.1083(2) 0.0453(10) Uani 1 2 d S . . C2' C 1.2559(4) 0.2500 -0.0475(3) 0.0500(11) Uani 1 2 d S . . H2' H 1.2913 0.2500 0.0195 0.060 Uiso 1 2 calc S . . C3' C 1.1083(4) 0.2500 -0.0974(2) 0.0396(9) Uani 1 2 d S . . C4' C 0.9822(4) 0.2500 -0.2796(3) 0.0416(10) Uani 1 2 d S . . C5' C 0.9881(4) 0.2500 -0.3758(3) 0.0504(11) Uani 1 2 d S . . H5' H 0.8983 0.2500 -0.4199 0.061 Uiso 1 2 calc S . . C6' C 1.0958(4) 0.2500 -0.4193(3) 0.0534(11) Uani 1 2 d S . . H6' H 1.0662 0.2500 -0.4866 0.064 Uiso 1 2 calc S . . C7' C 1.2408(4) 0.2500 -0.3805(3) 0.0449(10) Uani 1 2 d S . . C8' C 1.3047(4) 0.2500 -0.2835(3) 0.0455(10) Uani 1 2 d S . . H8' H 1.4038 0.2500 -0.2669 0.055 Uiso 1 2 calc S . . C9' C 1.2464(4) 0.2500 -0.2052(3) 0.0419(10) Uani 1 2 d S . . C10' C 1.1007(4) 0.2500 -0.2010(2) 0.0382(9) Uani 1 2 d S . . C11' C 1.4948(4) 0.2500 -0.0819(3) 0.0650(13) Uani 1 2 d S . . H11A H 1.5275 0.1456 -0.1144 0.098 Uiso 0.50 1 calc PR . . H11B H 1.5313 0.2341 -0.0131 0.098 Uiso 0.50 1 calc PR . . H11C H 1.5280 0.3704 -0.1010 0.098 Uiso 0.50 1 calc PR . . C41' C 0.8327(3) 0.2500 -0.2702(3) 0.0519(11) Uani 1 2 d S . . H41A H 0.8224 0.1487 -0.2269 0.078 Uiso 0.50 1 calc PR . . H41B H 0.7672 0.2290 -0.3326 0.078 Uiso 0.50 1 calc PR . . H41C H 0.8130 0.3722 -0.2450 0.078 Uiso 0.50 1 calc PR . . C71' C 1.3343(4) 0.2500 -0.4486(3) 0.0551(11) Uani 1 2 d S . . H71' H 1.4338 0.2500 -0.4096 0.066 Uiso 1 2 calc S . . C72' C 1.3100(3) 0.0709(5) -0.5102(2) 0.0673(9) Uani 1 1 d . . . H72A H 1.3261 -0.0412 -0.4693 0.101 Uiso 1 1 calc . . . H72B H 1.3746 0.0698 -0.5501 0.101 Uiso 1 1 calc . . . H72C H 1.2137 0.0698 -0.5505 0.101 Uiso 1 1 calc . . . B1 B 0.5017(5) 0.2500 0.2574(3) 0.0556(13) Uani 1 2 d S . . F1 F 0.6443(2) 0.2500 0.30808(17) 0.0818(9) Uani 1 2 d S . . F2 F 0.4925(3) 0.2500 0.16261(18) 0.1049(11) Uani 1 2 d S . . F3 F 0.4382(2) 0.0919(3) 0.28079(16) 0.1084(8) 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 O1 0.0517(19) 0.081(2) 0.0430(18) 0.000 0.0203(14) 0.000 C1 0.044(2) 0.049(2) 0.037(3) 0.000 0.017(2) 0.000 C2 0.034(2) 0.074(3) 0.045(3) 0.000 0.016(2) 0.000 C3 0.034(2) 0.077(3) 0.043(3) 0.000 0.0122(18) 0.000 C4 0.035(2) 0.050(2) 0.042(3) 0.000 0.0135(19) 0.000 C5 0.031(2) 0.066(3) 0.045(3) 0.000 0.016(2) 0.000 C6 0.035(2) 0.066(3) 0.042(3) 0.000 0.0059(18) 0.000 C7 0.038(2) 0.058(3) 0.039(2) 0.000 0.0116(19) 0.000 C1' 0.036(2) 0.067(3) 0.033(2) 0.000 0.0090(19) 0.000 C2' 0.040(2) 0.074(3) 0.034(2) 0.000 0.0073(19) 0.000 C3' 0.036(2) 0.045(2) 0.037(2) 0.000 0.0085(17) 0.000 C4' 0.036(2) 0.043(2) 0.045(3) 0.000 0.0105(19) 0.000 C5' 0.042(2) 0.064(3) 0.041(3) 0.000 0.0042(19) 0.000 C6' 0.045(3) 0.075(3) 0.039(2) 0.000 0.009(2) 0.000 C7' 0.041(2) 0.056(2) 0.036(2) 0.000 0.0084(19) 0.000 C8' 0.036(2) 0.058(3) 0.043(3) 0.000 0.0113(19) 0.000 C9' 0.037(2) 0.048(2) 0.041(2) 0.000 0.0123(19) 0.000 C10' 0.034(2) 0.041(2) 0.040(2) 0.000 0.0093(18) 0.000 C11' 0.033(2) 0.116(4) 0.043(2) 0.000 0.0062(19) 0.000 C41' 0.033(2) 0.076(3) 0.044(2) 0.000 0.0079(18) 0.000 C71' 0.045(2) 0.089(3) 0.035(2) 0.000 0.0160(19) 0.000 C72' 0.072(2) 0.083(2) 0.0522(19) -0.0022(17) 0.0262(16) 0.0092(17) B1 0.042(3) 0.082(4) 0.048(3) 0.000 0.021(2) 0.000 F1 0.0475(15) 0.141(2) 0.0574(16) 0.000 0.0150(12) 0.000 F2 0.0729(18) 0.196(3) 0.0458(18) 0.000 0.0168(13) 0.000 F3 0.0841(14) 0.1127(18) 0.1339(19) 0.0259(15) 0.0392(13) -0.0190(12) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 H1O 0.93(5) . ? O1 C1 1.361(4) . ? C1 C2 1.370(5) . ? C1 C6 1.394(5) . ? C2 C3 1.376(5) . ? C3 C4 1.390(5) . ? C4 C5 1.396(5) . ? C4 C7 1.442(5) . ? C5 C6 1.376(5) . ? C7 C3' 1.364(5) . ? C1' C2' 1.342(5) . ? C1' C9' 1.446(5) . ? C1' C11' 1.496(5) . ? C2' C3' 1.438(5) . ? C3' C10' 1.484(5) . ? C4' C10' 1.393(5) . ? C4' C5' 1.412(5) . ? C4' C41' 1.516(5) . ? C5' C6' 1.374(5) . ? C6' C7' 1.387(5) . ? C7' C8' 1.376(5) . ? C7' C71' 1.522(5) . ? C8' C9' 1.405(5) . ? C9' C10' 1.453(5) . ? C71' C72' 1.520(4) . ? C71' C72' 1.520(4) 4_565 ? B1 F2 1.353(5) . ? B1 F3 1.358(3) . ? B1 F3 1.358(3) 4_565 ? B1 F1 1.398(5) . ? 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 H1O O1 C1 114(3) . . ? O1 C1 C2 122.7(3) . . ? O1 C1 C6 118.2(3) . . ? C2 C1 C6 119.1(3) . . ? C1 C2 C3 119.6(3) . . ? C2 C3 C4 123.2(4) . . ? C3 C4 C5 116.0(3) . . ? C3 C4 C7 116.3(3) . . ? C5 C4 C7 127.8(3) . . ? C6 C5 C4 121.6(3) . . ? C5 C6 C1 120.4(3) . . ? C3' C7 C4 133.3(3) . . ? C2' C1' C9' 108.5(3) . . ? C2' C1' C11' 126.5(3) . . ? C9' C1' C11' 125.1(3) . . ? C1' C2' C3' 111.8(3) . . ? C7 C3' C2' 126.7(3) . . ? C7 C3' C10' 127.3(3) . . ? C2' C3' C10' 106.0(3) . . ? C10' C4' C5' 124.0(3) . . ? C10' C4' C41' 123.0(3) . . ? C5' C4' C41' 113.0(3) . . ? C6' C5' C4' 134.2(3) . . ? C5' C6' C7' 130.7(4) . . ? C8' C7' C6' 123.4(3) . . ? C8' C7' C71' 118.3(3) . . ? C6' C7' C71' 118.3(3) . . ? C7' C8' C9' 130.7(3) . . ? C8' C9' C1' 120.3(3) . . ? C8' C9' C10' 131.2(3) . . ? C1' C9' C10' 108.5(3) . . ? C4' C10' C9' 125.7(3) . . ? C4' C10' C3' 129.0(3) . . ? C9' C10' C3' 105.3(3) . . ? C72' C71' C72' 111.0(3) . 4_565 ? C72' C71' C7' 110.8(2) . . ? C72' C71' C7' 110.8(2) 4_565 . ? F2 B1 F3 110.2(3) . . ? F2 B1 F3 110.2(3) . 4_565 ? F3 B1 F3 109.0(4) . 4_565 ? F2 B1 F1 108.4(3) . . ? F3 B1 F1 109.5(3) . . ? F3 B1 F1 109.5(3) 4_565 . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 21.48 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.259 _refine_diff_density_min -0.136 _refine_diff_density_rms 0.031 data_kor_2 _database_code_CSD 195493 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C30 H38 O' _chemical_formula_weight 414.60 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 P2(1)/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 14.3240(9) _cell_length_b 12.5501(7) _cell_length_c 14.623(1) _cell_angle_alpha 90.00 _cell_angle_beta 100.000(3) _cell_angle_gamma 90.00 _cell_volume 2588.8(3) _cell_formula_units_Z 4 _cell_measurement_temperature 228(2) _cell_measurement_reflns_used 12613 _cell_measurement_theta_min 1.0 _cell_measurement_theta_max 21.0 _exptl_crystal_description prism _exptl_crystal_colour red _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.3 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.064 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 904 _exptl_absorpt_coefficient_mu 0.062 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 228(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 'Kappa CCD' _diffrn_measurement_method 'phi- and omega-scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 10312 _diffrn_reflns_av_R_equivalents 0.0357 _diffrn_reflns_av_sigmaI/netI 0.0300 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.15 _diffrn_reflns_theta_max 21.00 _reflns_number_total 2786 _reflns_number_gt 2198 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Kappa CCD' _computing_cell_refinement ? _computing_data_reduction 'DENZO and SCALEPACK' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; 1 : 1 disorder of position of C71' : C71; for correct calculation the overlaying methyl groups were splitted in two parts: C72'=C72 and C73'=C73 ; _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^)+(0.0722P)^2^+0.9832P] 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 riding _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.017(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2786 _refine_ls_number_parameters 292 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0665 _refine_ls_R_factor_gt 0.0505 _refine_ls_wR_factor_ref 0.1410 _refine_ls_wR_factor_gt 0.1306 _refine_ls_goodness_of_fit_ref 1.028 _refine_ls_restrained_S_all 1.028 _refine_ls_shift/su_max 0.006 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 1.33711(17) 0.15040(19) 0.11292(16) 0.0988(8) Uani 1 1 d . . . C1 C 1.28928(19) 0.1525(2) 0.1762(2) 0.0639(8) Uani 1 1 d . . . C2 C 1.31408(17) 0.2252(2) 0.25578(19) 0.0571(7) Uani 1 1 d . . . C3 C 1.25383(17) 0.2324(2) 0.31613(18) 0.0569(7) Uani 1 1 d . . . H3 H 1.2699 0.2782 0.3673 0.068 Uiso 1 1 calc . . . C4 C 1.16590(17) 0.17426(19) 0.30732(17) 0.0513(7) Uani 1 1 d . . . C5 C 1.14887(17) 0.09644(19) 0.23455(18) 0.0509(7) Uani 1 1 d . . . H5 H 1.0944 0.0536 0.2302 0.061 Uiso 1 1 calc . . . C6 C 1.20644(18) 0.08127(19) 0.17219(17) 0.0527(7) Uani 1 1 d . . . C7 C 1.10688(17) 0.1918(2) 0.37054(17) 0.0538(7) Uani 1 1 d . . . H7 H 1.1329 0.2314 0.4234 0.065 Uiso 1 1 calc . . . C21 C 1.40667(19) 0.2893(2) 0.2668(2) 0.0721(9) Uani 1 1 d . . . C22 C 1.4228(2) 0.3528(3) 0.3572(3) 0.0979(11) Uani 1 1 d . . . H22A H 1.4263 0.3043 0.4094 0.147 Uiso 1 1 calc . . . H22B H 1.3706 0.4020 0.3573 0.147 Uiso 1 1 calc . . . H22C H 1.4817 0.3923 0.3624 0.147 Uiso 1 1 calc . . . C23 C 1.4914(2) 0.2130(3) 0.2677(3) 0.0997(12) Uani 1 1 d . . . H23A H 1.4822 0.1720 0.2106 0.150 Uiso 1 1 calc . . . H23B H 1.4957 0.1650 0.3202 0.150 Uiso 1 1 calc . . . H23C H 1.5494 0.2541 0.2727 0.150 Uiso 1 1 calc . . . C24 C 1.4014(3) 0.3674(3) 0.1855(3) 0.1005(12) Uani 1 1 d . . . H24A H 1.3912 0.3282 0.1274 0.151 Uiso 1 1 calc . . . H24B H 1.4604 0.4069 0.1913 0.151 Uiso 1 1 calc . . . H24C H 1.3493 0.4167 0.1862 0.151 Uiso 1 1 calc . . . C61 C 1.1904(2) -0.0073(2) 0.09904(18) 0.0643(8) Uani 1 1 d . . . C62 C 1.1039(3) -0.0746(2) 0.1079(2) 0.0844(10) Uani 1 1 d . . . H62A H 1.0481 -0.0295 0.1007 0.127 Uiso 1 1 calc . . . H62B H 1.1133 -0.1082 0.1685 0.127 Uiso 1 1 calc . . . H62C H 1.0953 -0.1290 0.0600 0.127 Uiso 1 1 calc . . . C63 C 1.2770(3) -0.0806(3) 0.1107(3) 0.1027(12) Uani 1 1 d . . . H63A H 1.3329 -0.0391 0.1052 0.154 Uiso 1 1 calc . . . H63B H 1.2674 -0.1350 0.0628 0.154 Uiso 1 1 calc . . . H63C H 1.2855 -0.1142 0.1713 0.154 Uiso 1 1 calc . . . C64 C 1.1721(3) 0.0417(3) 0.0006(2) 0.0973(11) Uani 1 1 d . . . H64A H 1.2258 0.0854 -0.0078 0.146 Uiso 1 1 calc . . . H64B H 1.1154 0.0854 -0.0069 0.146 Uiso 1 1 calc . . . H64C H 1.1636 -0.0149 -0.0453 0.146 Uiso 1 1 calc . . . C3' C 1.01079(17) 0.15753(18) 0.36623(18) 0.0513(7) Uani 1 1 d . . . C1' C 0.85531(19) 0.1278(2) 0.2988(2) 0.0660(8) Uani 1 1 d . A . C2' C 0.94590(19) 0.1452(2) 0.28233(19) 0.0590(7) Uani 1 1 d . . . H2' H 0.9624 0.1483 0.2229 0.071 Uiso 1 1 calc . . . C4' C 0.9929(2) 0.14137(19) 0.5358(2) 0.0617(8) Uani 1 1 d . . . C5' C 0.9356(3) 0.1318(2) 0.6046(2) 0.0876(11) Uani 1 1 d . . . H5' H 0.9697 0.1315 0.6657 0.105 Uiso 1 1 calc . . . C6' C 0.8381(4) 0.1227(3) 0.5992(4) 0.1175(17) Uani 1 1 d . A . H6' H 0.8191 0.1198 0.6575 0.141 Uiso 1 1 calc . . . C7' C 0.7644(3) 0.1171(3) 0.5266(4) 0.1089(16) Uani 1 1 d . . . C8' C 0.7777(2) 0.1170(2) 0.4352(3) 0.0817(10) Uani 1 1 d . A . H8' H 0.7216 0.1076 0.3918 0.098 Uiso 1 1 calc . . . C9' C 0.85834(19) 0.12806(19) 0.3958(2) 0.0614(8) Uani 1 1 d . . . C10' C 0.95856(17) 0.14548(18) 0.44029(19) 0.0510(7) Uani 1 1 d . A . C11' C 0.7688(2) 0.1145(3) 0.2244(3) 0.1046(12) Uani 1 1 d . . . H11A H 0.7836 0.1369 0.1650 0.157 Uiso 1 1 calc R A . H11B H 0.7175 0.1579 0.2395 0.157 Uiso 1 1 calc R . . H11C H 0.7496 0.0403 0.2209 0.157 Uiso 1 1 calc R . . C41' C 1.0979(2) 0.1470(2) 0.5722(2) 0.0760(9) Uani 1 1 d . . . H41A H 1.1317 0.1068 0.5316 0.114 Uiso 1 1 calc R . . H41B H 1.1112 0.1170 0.6342 0.114 Uiso 1 1 calc R . . H41C H 1.1184 0.2207 0.5741 0.114 Uiso 1 1 calc R . . C71 C 0.6804(5) 0.1158(6) 0.5741(5) 0.068(2) Uani 0.50 1 d P A 1 H71 H 0.7046 0.1269 0.6411 0.081 Uiso 0.50 1 calc P B 1 C72 C 0.6132(2) 0.1987(3) 0.5457(3) 0.1142(14) Uani 0.50 1 d P A 1 H72A H 0.5609 0.1925 0.5795 0.171 Uiso 0.50 1 calc P C 1 H72B H 0.5894 0.1926 0.4796 0.171 Uiso 0.50 1 calc P D 1 H72C H 0.6436 0.2675 0.5586 0.171 Uiso 0.50 1 calc P E 1 C73 C 0.6371(2) 0.0016(3) 0.5643(3) 0.1117(13) Uani 0.50 1 d P A 1 H73A H 0.6864 -0.0504 0.5847 0.168 Uiso 0.50 1 calc P F 1 H73B H 0.6098 -0.0115 0.4998 0.168 Uiso 0.50 1 calc P G 1 H73C H 0.5881 -0.0043 0.6022 0.168 Uiso 0.50 1 calc P H 1 C71' C 0.6493(5) 0.0942(6) 0.5194(5) 0.0622(18) Uani 0.50 1 d P A 2 H71' H 0.6230 0.0828 0.4530 0.075 Uiso 0.50 1 calc P I 2 C72' C 0.6132(2) 0.1987(3) 0.5457(3) 0.1142(14) Uani 0.50 1 d P A 2 H72D H 0.6298 0.2536 0.5046 0.171 Uiso 0.50 1 calc P J 2 H72E H 0.6413 0.2155 0.6092 0.171 Uiso 0.50 1 calc P K 2 H72F H 0.5448 0.1954 0.5403 0.171 Uiso 0.50 1 calc P L 2 C73' C 0.6371(2) 0.0016(3) 0.5643(3) 0.1117(13) Uani 0.50 1 d P A 2 H73D H 0.6663 -0.0564 0.5357 0.168 Uiso 0.50 1 calc P M 2 H73E H 0.5699 -0.0124 0.5601 0.168 Uiso 0.50 1 calc P N 2 H73F H 0.6665 0.0077 0.6290 0.168 Uiso 0.50 1 calc P O 2 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 0.1013(17) 0.1125(19) 0.0992(17) -0.0147(14) 0.0638(15) -0.0146(14) C1 0.0624(18) 0.0639(18) 0.074(2) 0.0051(16) 0.0354(16) 0.0097(15) C2 0.0473(15) 0.0567(17) 0.0723(18) 0.0052(15) 0.0243(14) 0.0031(13) C3 0.0496(16) 0.0573(16) 0.0666(18) -0.0053(14) 0.0180(14) -0.0031(13) C4 0.0472(16) 0.0506(16) 0.0596(16) -0.0023(13) 0.0197(13) -0.0007(12) C5 0.0484(15) 0.0458(15) 0.0602(17) 0.0006(13) 0.0141(13) 0.0015(12) C6 0.0580(16) 0.0468(15) 0.0571(16) 0.0042(13) 0.0204(14) 0.0093(13) C7 0.0535(16) 0.0506(15) 0.0611(17) -0.0078(13) 0.0202(13) -0.0026(12) C21 0.0520(18) 0.072(2) 0.098(2) 0.0054(18) 0.0277(16) -0.0047(15) C22 0.061(2) 0.104(3) 0.131(3) -0.015(2) 0.021(2) -0.0297(18) C23 0.0501(18) 0.100(3) 0.155(3) 0.009(2) 0.033(2) 0.0019(17) C24 0.091(2) 0.085(2) 0.138(3) 0.026(2) 0.056(2) -0.0078(19) C61 0.087(2) 0.0511(16) 0.0594(18) -0.0016(14) 0.0250(15) 0.0099(15) C62 0.114(3) 0.0611(19) 0.080(2) -0.0164(16) 0.0226(19) -0.0103(19) C63 0.121(3) 0.074(2) 0.121(3) -0.011(2) 0.042(2) 0.037(2) C64 0.153(3) 0.083(2) 0.059(2) -0.0059(17) 0.028(2) -0.004(2) C3' 0.0480(16) 0.0437(15) 0.0663(18) -0.0056(13) 0.0210(14) -0.0010(12) C1' 0.0503(18) 0.0558(18) 0.094(2) -0.0045(16) 0.0167(16) -0.0021(13) C2' 0.0583(18) 0.0524(16) 0.0701(19) -0.0028(14) 0.0217(15) 0.0019(13) C4' 0.081(2) 0.0386(15) 0.073(2) 0.0022(13) 0.0334(17) 0.0113(13) C5' 0.123(3) 0.072(2) 0.082(2) 0.0150(17) 0.056(2) 0.029(2) C6' 0.143(4) 0.091(3) 0.151(4) 0.052(3) 0.114(4) 0.053(3) C7' 0.098(3) 0.076(2) 0.179(5) 0.054(3) 0.096(3) 0.033(2) C8' 0.063(2) 0.0554(19) 0.138(3) 0.0182(19) 0.050(2) 0.0028(14) C9' 0.0558(18) 0.0413(15) 0.094(2) 0.0038(14) 0.0313(16) 0.0011(12) C10' 0.0546(16) 0.0351(14) 0.0691(19) 0.0010(13) 0.0272(14) 0.0053(12) C11' 0.064(2) 0.121(3) 0.125(3) -0.010(2) 0.003(2) -0.008(2) C41' 0.093(2) 0.0650(19) 0.070(2) -0.0014(15) 0.0144(17) 0.0038(17) C71 0.062(5) 0.091(5) 0.052(4) 0.013(4) 0.017(4) -0.006(4) C72 0.068(2) 0.118(3) 0.164(4) -0.010(3) 0.042(2) 0.013(2) C73 0.069(2) 0.111(3) 0.158(4) 0.015(3) 0.027(2) -0.013(2) C71' 0.045(4) 0.090(5) 0.057(4) 0.019(4) 0.024(3) 0.004(3) C72' 0.068(2) 0.118(3) 0.164(4) -0.010(3) 0.042(2) 0.013(2) C73' 0.069(2) 0.111(3) 0.158(4) 0.015(3) 0.027(2) -0.013(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.243(3) . ? C1 C2 1.473(4) . ? C1 C6 1.479(4) . ? C2 C3 1.340(3) . ? C2 C21 1.536(4) . ? C3 C4 1.442(3) . ? C4 C7 1.374(3) . ? C4 C5 1.434(3) . ? C5 C6 1.345(3) . ? C6 C61 1.532(4) . ? C7 C3' 1.433(3) . ? C21 C22 1.527(5) . ? C21 C24 1.533(5) . ? C21 C23 1.544(4) . ? C61 C62 1.523(4) . ? C61 C63 1.530(4) . ? C61 C64 1.545(4) . ? C3' C2' 1.413(4) . ? C3' C10' 1.427(3) . ? C1' C2' 1.378(4) . ? C1' C9' 1.412(4) . ? C1' C11' 1.510(4) . ? C4' C10' 1.399(4) . ? C4' C5' 1.410(4) . ? C4' C41' 1.508(4) . ? C5' C6' 1.390(6) . ? C6' C7' 1.362(6) . ? C7' C8' 1.382(6) . ? C7' C71 1.491(8) . ? C7' C71' 1.660(8) . ? C8' C9' 1.384(4) . ? C9' C10' 1.486(4) . ? C71 C72 1.430(8) . ? C71 C73 1.557(9) . ? 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 O1 C1 C2 120.9(3) . . ? O1 C1 C6 120.0(3) . . ? C2 C1 C6 119.1(2) . . ? C3 C2 C1 117.9(2) . . ? C3 C2 C21 122.6(3) . . ? C1 C2 C21 119.5(2) . . ? C2 C3 C4 124.0(2) . . ? C7 C4 C5 124.3(2) . . ? C7 C4 C3 119.3(2) . . ? C5 C4 C3 116.4(2) . . ? C6 C5 C4 123.7(2) . . ? C5 C6 C1 118.0(2) . . ? C5 C6 C61 122.7(2) . . ? C1 C6 C61 119.2(2) . . ? C4 C7 C3' 128.4(2) . . ? C22 C21 C24 108.5(3) . . ? C22 C21 C2 111.2(2) . . ? C24 C21 C2 109.2(3) . . ? C22 C21 C23 108.4(3) . . ? C24 C21 C23 109.6(3) . . ? C2 C21 C23 109.8(2) . . ? C62 C61 C63 108.2(3) . . ? C62 C61 C6 111.7(2) . . ? C63 C61 C6 109.8(2) . . ? C62 C61 C64 106.9(3) . . ? C63 C61 C64 110.2(3) . . ? C6 C61 C64 110.0(2) . . ? C2' C3' C10' 107.1(2) . . ? C2' C3' C7 123.6(2) . . ? C10' C3' C7 128.7(2) . . ? C2' C1' C9' 108.0(3) . . ? C2' C1' C11' 124.9(3) . . ? C9' C1' C11' 127.1(3) . . ? C1' C2' C3' 111.3(2) . . ? C10' C4' C5' 124.7(3) . . ? C10' C4' C41' 120.5(2) . . ? C5' C4' C41' 114.9(3) . . ? C6' C5' C4' 132.0(4) . . ? C7' C6' C5' 133.2(4) . . ? C6' C7' C8' 122.4(3) . . ? C6' C7' C71 102.5(5) . . ? C8' C7' C71 135.1(5) . . ? C6' C7' C71' 133.2(4) . . ? C8' C7' C71' 103.9(5) . . ? C71 C7' C71' 32.1(3) . . ? C7' C8' C9' 131.8(4) . . ? C8' C9' C1' 122.4(3) . . ? C8' C9' C10' 130.2(3) . . ? C1' C9' C10' 107.4(2) . . ? C4' C10' C3' 128.5(2) . . ? C4' C10' C9' 125.2(2) . . ? C3' C10' C9' 106.1(2) . . ? C72 C71 C7' 114.4(5) . . ? C72 C71 C73 113.9(5) . . ? C7' C71 C73 107.9(5) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 21.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.135 _refine_diff_density_min -0.192 _refine_diff_density_rms 0.030