# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full CrystEngComm _journal_coden_cambridge 1350 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Saikat Kumar Seth' _publ_contact_author_email saikatim@yahoo.co.in loop_ _publ_author_name 'Saikat K. Seth' 'Tanusree Kar' data_d4a _database_code_depnum_ccdc_archive 'CCDC 757645' #TrackingRef 'D4A.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 7-methoxy-5-methyl-4H-chromen-4-one ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C11 H10 O3' _chemical_formula_weight 190.19 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting MONOCLINIC _symmetry_space_group_name_H-M 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 3.8431(4) _cell_length_b 20.241(2) _cell_length_c 11.3553(11) _cell_angle_alpha 90.00 _cell_angle_beta 95.841(2) _cell_angle_gamma 90.00 _cell_volume 878.73(15) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 1600 _cell_measurement_theta_min 1.5 _cell_measurement_theta_max 25.5 _exptl_crystal_description PLATE _exptl_crystal_colour BROWN _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.438 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 400 _exptl_absorpt_coefficient_mu 0.105 _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 150(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 'BRUKER SMART APEX II CCD AREA DETECTOR' _diffrn_measurement_method 'OMEGA SCAN' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8025 _diffrn_reflns_av_R_equivalents 0.0193 _diffrn_reflns_av_sigmaI/netI 0.0136 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.01 _diffrn_reflns_theta_max 25.00 _reflns_number_total 1558 _reflns_number_gt 1449 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'BRUKER SMART APEX II' _computing_cell_refinement 'BRUKER SMART APEX II' _computing_data_reduction 'BRUKER AXS SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-3 for Windows (Version 1.06) and CAMERON' _computing_publication_material 'SHELXL97 and PARST 95 (Nardelli, 1995)' _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^)+(0.0460P)^2^+0.3577P] 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 1558 _refine_ls_number_parameters 129 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0378 _refine_ls_R_factor_gt 0.0356 _refine_ls_wR_factor_ref 0.1002 _refine_ls_wR_factor_gt 0.0988 _refine_ls_goodness_of_fit_ref 1.132 _refine_ls_restrained_S_all 1.132 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.0691(3) 0.35942(5) 0.59406(9) 0.0264(3) Uani 1 1 d . . . C6 C 0.3887(3) 0.36085(7) 0.78986(12) 0.0204(3) Uani 1 1 d . . . C2 C 0.6078(4) 0.46728(7) 0.85821(12) 0.0234(3) Uani 1 1 d . . . H2 H 0.7284 0.4933 0.9162 0.028 Uiso 1 1 calc R . . C1 C 0.5733(3) 0.40084(7) 0.87900(12) 0.0214(3) Uani 1 1 d . . . O2 O 0.4377(3) 0.25704(5) 0.88973(9) 0.0305(3) Uani 1 1 d . . . C4 C 0.2879(4) 0.45960(7) 0.66567(12) 0.0229(3) Uani 1 1 d . . . H4 H 0.1928 0.4787 0.5952 0.028 Uiso 1 1 calc R . . C8 C 0.1319(4) 0.25916(7) 0.70043(13) 0.0266(3) Uani 1 1 d . . . H8 H 0.0853 0.2141 0.7022 0.032 Uiso 1 1 calc R . . C7 C 0.3308(4) 0.28947(7) 0.80173(12) 0.0225(3) Uani 1 1 d . . . C5 C 0.2522(3) 0.39235(7) 0.68605(12) 0.0214(3) Uani 1 1 d . . . O3 O 0.5255(3) 0.56290(5) 0.74478(9) 0.0286(3) Uani 1 1 d . . . C3 C 0.4677(3) 0.49702(7) 0.75272(12) 0.0226(3) Uani 1 1 d . . . C10 C 0.7339(4) 0.37284(7) 0.99465(12) 0.0252(3) Uani 1 1 d . . . H10A H 0.8432 0.4077 1.0424 0.038 Uiso 1 1 calc R . . H10B H 0.9061 0.3403 0.9798 0.038 Uiso 1 1 calc R . . H10C H 0.5550 0.3526 1.0356 0.038 Uiso 1 1 calc R . . C9 C 0.0145(4) 0.29374(7) 0.60524(13) 0.0267(3) Uani 1 1 d . . . H9 H -0.1120 0.2717 0.5430 0.032 Uiso 1 1 calc R . . C11 C 0.3569(4) 0.59636(7) 0.64356(14) 0.0315(4) Uani 1 1 d . . . H11A H 0.4358 0.5781 0.5729 0.047 Uiso 1 1 calc R . . H11B H 0.4137 0.6425 0.6484 0.047 Uiso 1 1 calc R . . H11C H 0.1082 0.5909 0.6415 0.047 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 0.0315(6) 0.0252(5) 0.0210(5) -0.0020(4) -0.0049(4) -0.0010(4) C6 0.0180(7) 0.0227(7) 0.0209(7) -0.0008(5) 0.0037(5) 0.0030(5) C2 0.0212(7) 0.0260(7) 0.0226(7) -0.0042(6) 0.0001(6) -0.0011(6) C1 0.0175(7) 0.0258(7) 0.0210(7) -0.0012(5) 0.0024(5) 0.0025(5) O2 0.0389(6) 0.0240(6) 0.0269(6) 0.0036(4) -0.0046(5) 0.0017(4) C4 0.0236(7) 0.0247(7) 0.0203(7) 0.0027(6) 0.0014(5) 0.0035(6) C8 0.0284(8) 0.0223(7) 0.0288(8) -0.0036(6) 0.0009(6) -0.0015(6) C7 0.0212(7) 0.0227(7) 0.0239(7) -0.0013(6) 0.0033(6) 0.0029(5) C5 0.0197(7) 0.0242(7) 0.0202(7) -0.0031(5) 0.0016(5) 0.0010(5) O3 0.0336(6) 0.0210(5) 0.0303(6) 0.0018(4) -0.0005(4) -0.0026(4) C3 0.0208(7) 0.0214(7) 0.0263(7) -0.0003(6) 0.0055(6) 0.0005(5) C10 0.0254(7) 0.0270(7) 0.0221(7) -0.0006(6) -0.0028(6) -0.0007(6) C9 0.0283(8) 0.0239(7) 0.0271(8) -0.0066(6) -0.0006(6) -0.0028(6) C11 0.0338(8) 0.0243(8) 0.0359(9) 0.0070(6) 0.0016(7) 0.0010(6) _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 C9 1.3539(18) . ? O1 C5 1.3716(16) . ? C6 C5 1.3947(19) . ? C6 C1 1.4274(19) . ? C6 C7 1.470(2) . ? C2 C1 1.374(2) . ? C2 C3 1.399(2) . ? C2 H2 0.9300 . ? C1 C10 1.5039(18) . ? O2 C7 1.2307(17) . ? C4 C3 1.375(2) . ? C4 C5 1.390(2) . ? C4 H4 0.9300 . ? C8 C9 1.328(2) . ? C8 C7 1.451(2) . ? C8 H8 0.9300 . ? O3 C3 1.3563(17) . ? O3 C11 1.4311(18) . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C9 H9 0.9300 . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? 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 C9 O1 C5 118.57(11) . . ? C5 C6 C1 117.20(13) . . ? C5 C6 C7 118.65(12) . . ? C1 C6 C7 124.15(12) . . ? C1 C2 C3 122.21(13) . . ? C1 C2 H2 118.9 . . ? C3 C2 H2 118.9 . . ? C2 C1 C6 118.87(13) . . ? C2 C1 C10 118.73(12) . . ? C6 C1 C10 122.40(12) . . ? C3 C4 C5 118.09(13) . . ? C3 C4 H4 121.0 . . ? C5 C4 H4 121.0 . . ? C9 C8 C7 122.05(14) . . ? C9 C8 H8 119.0 . . ? C7 C8 H8 119.0 . . ? O2 C7 C8 121.57(13) . . ? O2 C7 C6 123.89(13) . . ? C8 C7 C6 114.54(12) . . ? O1 C5 C4 113.63(12) . . ? O1 C5 C6 122.76(13) . . ? C4 C5 C6 123.62(13) . . ? C3 O3 C11 117.05(11) . . ? O3 C3 C4 124.60(13) . . ? O3 C3 C2 115.39(12) . . ? C4 C3 C2 120.02(13) . . ? C1 C10 H10A 109.5 . . ? C1 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C1 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C8 C9 O1 123.43(13) . . ? C8 C9 H9 118.3 . . ? O1 C9 H9 118.3 . . ? O3 C11 H11A 109.5 . . ? O3 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? O3 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C3 C2 C1 C6 0.1(2) . . . . ? C3 C2 C1 C10 179.67(13) . . . . ? C5 C6 C1 C2 -0.21(19) . . . . ? C7 C6 C1 C2 -179.35(13) . . . . ? C5 C6 C1 C10 -179.78(12) . . . . ? C7 C6 C1 C10 1.1(2) . . . . ? C9 C8 C7 O2 179.77(14) . . . . ? C9 C8 C7 C6 0.2(2) . . . . ? C5 C6 C7 O2 -179.50(13) . . . . ? C1 C6 C7 O2 -0.4(2) . . . . ? C5 C6 C7 C8 0.08(18) . . . . ? C1 C6 C7 C8 179.21(12) . . . . ? C9 O1 C5 C4 -179.06(12) . . . . ? C9 O1 C5 C6 0.95(19) . . . . ? C3 C4 C5 O1 -179.98(12) . . . . ? C3 C4 C5 C6 0.0(2) . . . . ? C1 C6 C5 O1 -179.85(12) . . . . ? C7 C6 C5 O1 -0.6(2) . . . . ? C1 C6 C5 C4 0.2(2) . . . . ? C7 C6 C5 C4 179.36(13) . . . . ? C11 O3 C3 C4 6.5(2) . . . . ? C11 O3 C3 C2 -173.89(12) . . . . ? C5 C4 C3 O3 179.40(13) . . . . ? C5 C4 C3 C2 -0.2(2) . . . . ? C1 C2 C3 O3 -179.49(13) . . . . ? C1 C2 C3 C4 0.1(2) . . . . ? C7 C8 C9 O1 0.1(2) . . . . ? C5 O1 C9 C8 -0.7(2) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.173 _refine_diff_density_min -0.204 _refine_diff_density_rms 0.040 data_a6a _database_code_depnum_ccdc_archive 'CCDC 794660' #TrackingRef 'a6a.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C11 H10 O2' _chemical_formula_weight 174.19 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting MONOCLINIC _symmetry_space_group_name_H-M 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 7.2934(18) _cell_length_b 13.423(3) _cell_length_c 9.151(2) _cell_angle_alpha 90.00 _cell_angle_beta 103.183(3) _cell_angle_gamma 90.00 _cell_volume 872.3(4) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 370 _cell_measurement_theta_min 1.5 _cell_measurement_theta_max 25.0 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.19 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.326 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 368 _exptl_absorpt_coefficient_mu 0.091 _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 150(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 'BRUKER SMART APEX II CCD AREA DETECTOR' _diffrn_measurement_method 'OMEGA SCAN' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6006 _diffrn_reflns_av_R_equivalents 0.0227 _diffrn_reflns_av_sigmaI/netI 0.0180 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.74 _diffrn_reflns_theta_max 25.00 _reflns_number_total 1536 _reflns_number_gt 1381 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'BRUKER SMART APEX II' _computing_cell_refinement 'BRUKER SMART APEX II' _computing_data_reduction 'BRUKER AXS SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-3 for Windows (Version 1.06) and CAMERON' _computing_publication_material 'SHELXL97 and PARST 95 (Nardelli, 1995)' _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^)+(0.0529P)^2^+0.2191P] 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 1536 _refine_ls_number_parameters 120 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0378 _refine_ls_R_factor_gt 0.0350 _refine_ls_wR_factor_ref 0.0976 _refine_ls_wR_factor_gt 0.0952 _refine_ls_goodness_of_fit_ref 1.086 _refine_ls_restrained_S_all 1.086 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.19329(11) 0.89009(6) 0.04271(9) 0.0227(2) Uani 1 1 d . . . O2 O 0.46235(13) 1.09901(7) 0.34190(10) 0.0303(3) Uani 1 1 d . . . C6 C 0.32406(16) 1.05569(9) 0.08941(13) 0.0212(3) Uani 1 1 d . . . C4 C 0.17420(16) 0.99871(9) -0.16159(13) 0.0222(3) Uani 1 1 d . . . H4 H 0.1110 0.9488 -0.2238 0.027 Uiso 1 1 calc R . . C2 C 0.30521(17) 1.16345(9) -0.12493(14) 0.0238(3) Uani 1 1 d . . . H2 H 0.3307 1.2245 -0.1640 0.029 Uiso 1 1 calc R . . C8 C 0.33472(16) 0.93695(10) 0.29430(13) 0.0243(3) Uani 1 1 d . . . H8 H 0.3662 0.9192 0.3952 0.029 Uiso 1 1 calc R . . C1 C 0.36000(16) 1.14685(9) 0.02701(13) 0.0234(3) Uani 1 1 d . . . H1 H 0.4219 1.1970 0.0894 0.028 Uiso 1 1 calc R . . C5 C 0.23176(16) 0.98255(9) -0.00799(13) 0.0206(3) Uani 1 1 d . . . C7 C 0.38125(16) 1.03559(10) 0.25130(13) 0.0232(3) Uani 1 1 d . . . C3 C 0.21093(16) 1.08905(9) -0.22190(13) 0.0234(3) Uani 1 1 d . . . C10 C 0.19875(18) 0.76578(10) 0.22377(14) 0.0279(3) Uani 1 1 d . . . H10A H 0.2753 0.7206 0.1821 0.042 Uiso 1 1 calc R . . H10B H 0.0683 0.7537 0.1790 0.042 Uiso 1 1 calc R . . H10C H 0.2214 0.7557 0.3302 0.042 Uiso 1 1 calc R . . C9 C 0.24718(16) 0.86995(9) 0.19276(13) 0.0228(3) Uani 1 1 d . . . C11 C 0.15195(19) 1.10767(11) -0.38808(14) 0.0302(3) Uani 1 1 d . . . H11A H 0.2428 1.0788 -0.4367 0.045 Uiso 1 1 calc R . . H11B H 0.1445 1.1781 -0.4065 0.045 Uiso 1 1 calc R . . H11C H 0.0309 1.0779 -0.4270 0.045 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 0.0258(5) 0.0221(5) 0.0199(5) 0.0006(3) 0.0047(3) 0.0006(3) O2 0.0372(5) 0.0307(5) 0.0213(5) -0.0041(4) 0.0031(4) -0.0031(4) C6 0.0193(6) 0.0244(7) 0.0206(6) -0.0008(5) 0.0058(5) 0.0037(5) C4 0.0213(6) 0.0250(7) 0.0200(6) -0.0039(5) 0.0041(5) 0.0010(5) C2 0.0237(6) 0.0237(6) 0.0254(6) 0.0021(5) 0.0081(5) 0.0011(5) C8 0.0233(6) 0.0304(7) 0.0197(6) 0.0032(5) 0.0058(5) 0.0047(5) C1 0.0214(6) 0.0254(6) 0.0234(6) -0.0036(5) 0.0051(5) 0.0002(5) C5 0.0187(6) 0.0216(7) 0.0226(6) 0.0013(5) 0.0069(5) 0.0043(5) C7 0.0204(6) 0.0288(7) 0.0206(6) -0.0023(5) 0.0055(5) 0.0033(5) C3 0.0212(6) 0.0290(7) 0.0208(6) 0.0006(5) 0.0065(5) 0.0036(5) C10 0.0287(7) 0.0271(7) 0.0278(7) 0.0037(5) 0.0062(5) 0.0027(5) C9 0.0199(6) 0.0282(7) 0.0207(6) 0.0033(5) 0.0060(5) 0.0057(5) C11 0.0336(7) 0.0345(8) 0.0224(7) 0.0020(5) 0.0061(5) -0.0026(6) _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 C9 1.3664(14) . ? O1 C5 1.3762(15) . ? O2 C7 1.2403(15) . ? C6 C5 1.3920(18) . ? C6 C1 1.4001(18) . ? C6 C7 1.4696(17) . ? C4 C3 1.3836(18) . ? C4 C5 1.3892(17) . ? C4 H4 0.9300 . ? C2 C1 1.3744(18) . ? C2 C3 1.4069(18) . ? C2 H2 0.9300 . ? C8 C9 1.3451(18) . ? C8 C7 1.4435(19) . ? C8 H8 0.9300 . ? C1 H1 0.9300 . ? C3 C11 1.5039(17) . ? C10 C9 1.4853(18) . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? 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 C9 O1 C5 118.89(10) . . ? C5 C6 C1 117.61(11) . . ? C5 C6 C7 120.04(11) . . ? C1 C6 C7 122.35(11) . . ? C3 C4 C5 119.94(11) . . ? C3 C4 H4 120.0 . . ? C5 C4 H4 120.0 . . ? C1 C2 C3 120.70(12) . . ? C1 C2 H2 119.7 . . ? C3 C2 H2 119.7 . . ? C9 C8 C7 121.94(11) . . ? C9 C8 H8 119.0 . . ? C7 C8 H8 119.0 . . ? C2 C1 C6 121.06(11) . . ? C2 C1 H1 119.5 . . ? C6 C1 H1 119.5 . . ? O1 C5 C4 116.37(11) . . ? O1 C5 C6 121.75(11) . . ? C4 C5 C6 121.88(11) . . ? O2 C7 C8 123.59(11) . . ? O2 C7 C6 122.02(12) . . ? C8 C7 C6 114.39(11) . . ? C4 C3 C2 118.80(11) . . ? C4 C3 C11 120.81(11) . . ? C2 C3 C11 120.39(11) . . ? C9 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C9 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C8 C9 O1 122.98(11) . . ? C8 C9 C10 126.41(11) . . ? O1 C9 C10 110.60(10) . . ? C3 C11 H11A 109.5 . . ? C3 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C3 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C3 C2 C1 C6 0.13(18) . . . . ? C5 C6 C1 C2 0.27(17) . . . . ? C7 C6 C1 C2 179.85(10) . . . . ? C9 O1 C5 C4 179.83(9) . . . . ? C9 O1 C5 C6 0.10(16) . . . . ? C3 C4 C5 O1 -178.72(10) . . . . ? C3 C4 C5 C6 1.01(17) . . . . ? C1 C6 C5 O1 178.87(10) . . . . ? C7 C6 C5 O1 -0.72(17) . . . . ? C1 C6 C5 C4 -0.85(17) . . . . ? C7 C6 C5 C4 179.56(10) . . . . ? C9 C8 C7 O2 -179.77(11) . . . . ? C9 C8 C7 C6 0.33(17) . . . . ? C5 C6 C7 O2 -179.40(11) . . . . ? C1 C6 C7 O2 1.03(18) . . . . ? C5 C6 C7 C8 0.50(16) . . . . ? C1 C6 C7 C8 -179.07(10) . . . . ? C5 C4 C3 C2 -0.57(17) . . . . ? C5 C4 C3 C11 179.26(11) . . . . ? C1 C2 C3 C4 0.01(17) . . . . ? C1 C2 C3 C11 -179.81(11) . . . . ? C7 C8 C9 O1 -1.00(18) . . . . ? C7 C8 C9 C10 177.75(11) . . . . ? C5 O1 C9 C8 0.79(16) . . . . ? C5 O1 C9 C10 -178.15(9) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.208 _refine_diff_density_min -0.186 _refine_diff_density_rms 0.040