# Electronic Supplementary Material (ESI) for Chemical Science # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full 'Chemical Science' #TrackingRef '- bond.cif' _journal_coden_Cambridge 1475 _publ_contact_author_name 'Andrew D. Bond' _publ_contact_author_address ; University of Southern Denmark Department of Physics and Chemistry Campusvej 55 5230 Odense Denmark ; _publ_contact_author_email adb@chem.sdu.dk _publ_contact_author_fax '+45 6615 8780' _publ_contact_author_phone '+45 6650 2545' loop_ _publ_author_name S.Varughese M.S.R.N.Kiran K.Solanko A.D.Bond U.Ramamurty ; G.Desiraju ; data_123K _database_code_depnum_ccdc_archive 'CCDC 820697' #TrackingRef '- bond.cif' _chemical_name_systematic ? _chemical_name_common 'Aspirin form II' _chemical_melting_point ? _chemical_formula_moiety 'C9 H8 O4' _chemical_formula_sum 'C9 H8 O4' _chemical_formula_weight 180.15 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' 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 12.1016(4) _cell_length_b 6.4721(2) _cell_length_c 11.3344(4) _cell_angle_alpha 90.00 _cell_angle_beta 111.593(1) _cell_angle_gamma 90.00 _cell_volume 825.44(5) _cell_formula_units_Z 4 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used 5080 _cell_measurement_theta_min 3.62 _cell_measurement_theta_max 25.48 _exptl_crystal_description lath _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.450 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 376 _exptl_absorpt_coefficient_mu 0.116 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.861 _exptl_absorpt_correction_T_max 0.991 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2008)' _exptl_special_details ? _diffrn_ambient_temperature 123(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 Nonius X8APEX-II CCD' _diffrn_measurement_method '\w and \f scans' _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% ? _diffrn_reflns_number 12065 _diffrn_reflns_av_R_equivalents 0.0282 _diffrn_reflns_av_sigmaI/netI 0.0208 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 3.62 _diffrn_reflns_theta_max 25.68 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.68 _diffrn_measured_fraction_theta_full 0.997 _reflns_number_total 1552 _reflns_number_gt 1445 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'APEX2 v2010.1-2 (Bruker, 2010)' _computing_cell_refinement 'SAINT v.7.68a (Bruker, 2010)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXTL v.6.12 (Sheldrick, 2008)' _computing_structure_refinement SHELXTL _computing_molecular_graphics SHELXTL _computing_publication_material SHELXTL _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^)+(0.0277P)^2^+0.5719P] 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 1552 _refine_ls_number_parameters 123 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0522 _refine_ls_R_factor_gt 0.0473 _refine_ls_wR_factor_ref 0.0946 _refine_ls_wR_factor_gt 0.0922 _refine_ls_goodness_of_fit_ref 1.231 _refine_ls_restrained_S_all 1.231 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.274 _refine_diff_density_min -0.211 _refine_diff_density_rms 0.048 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 0.62354(11) 0.1419(2) 0.61266(11) 0.0203(3) Uani 1 1 d . . . H1 H 0.577(2) 0.025(5) 0.602(2) 0.060(8) Uiso 1 1 d . . . O2 O 0.50970(11) 0.1879(2) 0.40933(11) 0.0212(3) Uani 1 1 d . . . O3 O 0.78878(10) 0.41876(19) 0.72945(10) 0.0171(3) Uani 1 1 d . . . O4 O 0.90669(11) 0.2189(2) 0.66325(11) 0.0215(3) Uani 1 1 d . . . C1 C 0.65418(15) 0.4419(3) 0.50750(16) 0.0154(4) Uani 1 1 d . . . C2 C 0.74806(15) 0.5203(3) 0.61181(16) 0.0162(4) Uani 1 1 d . . . C3 C 0.80069(16) 0.7061(3) 0.60519(17) 0.0196(4) Uani 1 1 d . . . H3 H 0.8632 0.7580 0.6776 0.024 Uiso 1 1 calc R . . C4 C 0.76267(16) 0.8174(3) 0.49303(18) 0.0215(4) Uani 1 1 d . . . H4 H 0.7997 0.9449 0.4882 0.026 Uiso 1 1 calc R . . C5 C 0.67053(16) 0.7425(3) 0.38781(17) 0.0195(4) Uani 1 1 d . . . H5 H 0.6444 0.8182 0.3106 0.023 Uiso 1 1 calc R . . C6 C 0.61699(15) 0.5578(3) 0.39559(16) 0.0173(4) Uani 1 1 d . . . H6 H 0.5534 0.5081 0.3233 0.021 Uiso 1 1 calc R . . C7 C 0.59016(15) 0.2458(3) 0.50601(15) 0.0151(4) Uani 1 1 d . . . C8 C 0.86823(15) 0.2623(3) 0.74362(16) 0.0166(4) Uani 1 1 d . . . C9 C 0.89840(17) 0.1611(3) 0.86922(17) 0.0249(5) Uani 1 1 d . . . H7 H 0.9545 0.0480 0.8770 0.037 Uiso 1 1 calc R . . H8 H 0.8259 0.1059 0.8769 0.037 Uiso 1 1 calc R . . H9 H 0.9347 0.2625 0.9366 0.037 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 0.0210(7) 0.0206(7) 0.0158(6) 0.0040(5) 0.0027(5) -0.0035(6) O2 0.0216(7) 0.0216(7) 0.0162(6) 0.0006(5) 0.0020(5) -0.0046(6) O3 0.0178(6) 0.0221(7) 0.0100(6) 0.0000(5) 0.0034(5) 0.0013(5) O4 0.0217(7) 0.0270(8) 0.0164(7) 0.0015(6) 0.0076(6) 0.0050(6) C1 0.0138(8) 0.0172(9) 0.0157(9) -0.0008(7) 0.0060(7) 0.0030(7) C2 0.0158(9) 0.0190(9) 0.0144(9) -0.0006(7) 0.0063(7) 0.0047(7) C3 0.0171(9) 0.0211(10) 0.0190(10) -0.0047(8) 0.0045(8) -0.0016(8) C4 0.0208(10) 0.0178(10) 0.0267(10) -0.0007(8) 0.0097(8) -0.0015(8) C5 0.0191(9) 0.0193(10) 0.0199(9) 0.0043(8) 0.0069(8) 0.0032(8) C6 0.0150(9) 0.0208(10) 0.0152(9) -0.0013(7) 0.0045(7) 0.0020(8) C7 0.0143(9) 0.0180(9) 0.0136(9) 0.0004(7) 0.0056(7) 0.0028(7) C8 0.0128(9) 0.0182(9) 0.0170(9) -0.0019(7) 0.0032(7) -0.0019(7) C9 0.0224(10) 0.0343(12) 0.0184(9) 0.0074(8) 0.0080(8) 0.0041(9) _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 C7 1.310(2) . ? O1 H1 0.93(3) . ? O2 C7 1.226(2) . ? O3 C8 1.365(2) . ? O3 C2 1.403(2) . ? O4 C8 1.199(2) . ? C1 C6 1.398(2) . ? C1 C2 1.399(2) . ? C1 C7 1.484(3) . ? C2 C3 1.376(3) . ? C3 C4 1.384(3) . ? C3 H3 0.9500 . ? C4 C5 1.386(3) . ? C4 H4 0.9500 . ? C5 C6 1.378(3) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C8 C9 1.485(2) . ? C9 H7 0.9800 . ? C9 H8 0.9800 . ? C9 H9 0.9800 . ? 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 C7 O1 H1 109.5(16) . . ? C8 O3 C2 116.43(13) . . ? C6 C1 C2 117.57(16) . . ? C6 C1 C7 117.14(15) . . ? C2 C1 C7 125.29(15) . . ? C3 C2 C1 121.26(16) . . ? C3 C2 O3 116.96(15) . . ? C1 C2 O3 121.70(16) . . ? C2 C3 C4 120.07(16) . . ? C2 C3 H3 120.0 . . ? C4 C3 H3 120.0 . . ? C3 C4 C5 119.88(18) . . ? C3 C4 H4 120.1 . . ? C5 C4 H4 120.1 . . ? C6 C5 C4 119.78(17) . . ? C6 C5 H5 120.1 . . ? C4 C5 H5 120.1 . . ? C5 C6 C1 121.43(16) . . ? C5 C6 H6 119.3 . . ? C1 C6 H6 119.3 . . ? O2 C7 O1 122.79(16) . . ? O2 C7 C1 120.73(15) . . ? O1 C7 C1 116.48(15) . . ? O4 C8 O3 122.55(16) . . ? O4 C8 C9 126.71(17) . . ? O3 C8 C9 110.74(15) . . ? C8 C9 H7 109.5 . . ? C8 C9 H8 109.5 . . ? H7 C9 H8 109.5 . . ? C8 C9 H9 109.5 . . ? H7 C9 H9 109.5 . . ? H8 C9 H9 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 C6 C1 C2 C3 1.0(3) . . . . ? C7 C1 C2 C3 -178.69(16) . . . . ? C6 C1 C2 O3 177.70(15) . . . . ? C7 C1 C2 O3 -2.0(3) . . . . ? C8 O3 C2 C3 -99.59(18) . . . . ? C8 O3 C2 C1 83.55(19) . . . . ? C1 C2 C3 C4 -1.4(3) . . . . ? O3 C2 C3 C4 -178.23(16) . . . . ? C2 C3 C4 C5 0.7(3) . . . . ? C3 C4 C5 C6 0.2(3) . . . . ? C4 C5 C6 C1 -0.6(3) . . . . ? C2 C1 C6 C5 0.0(3) . . . . ? C7 C1 C6 C5 179.69(16) . . . . ? C6 C1 C7 O2 1.3(2) . . . . ? C2 C1 C7 O2 -179.02(16) . . . . ? C6 C1 C7 O1 -177.98(15) . . . . ? C2 C1 C7 O1 1.7(2) . . . . ? C2 O3 C8 O4 3.7(2) . . . . ? C2 O3 C8 C9 -176.76(15) . . . . ? data_298K _database_code_depnum_ccdc_archive 'CCDC 820698' #TrackingRef '- bond.cif' _chemical_name_systematic ? _chemical_name_common 'Aspirin form II' _chemical_melting_point ? _chemical_formula_moiety 'C9 H8 O4' _chemical_formula_sum 'C9 H8 O4' _chemical_formula_weight 180.15 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' 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 12.3578(7) _cell_length_b 6.5315(8) _cell_length_c 11.4964(7) _cell_angle_alpha 90.00 _cell_angle_beta 112.436(3) _cell_angle_gamma 90.00 _cell_volume 857.69(13) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 3816 _cell_measurement_theta_min 3.56 _cell_measurement_theta_max 22.83 _exptl_crystal_description lath _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.395 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 376 _exptl_absorpt_coefficient_mu 0.111 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.882 _exptl_absorpt_correction_T_max 0.991 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2008)' _exptl_special_details ? _diffrn_ambient_temperature 120(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 Nonius X8APEX-II CCD' _diffrn_measurement_method '\w and \f scans' _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% ? _diffrn_reflns_number 15790 _diffrn_reflns_av_R_equivalents 0.0387 _diffrn_reflns_av_sigmaI/netI 0.0238 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 3.56 _diffrn_reflns_theta_max 25.43 _diffrn_measured_fraction_theta_max 0.972 _diffrn_reflns_theta_full 25.43 _diffrn_measured_fraction_theta_full 0.972 _reflns_number_total 1527 _reflns_number_gt 1083 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'APEX2 v2010.1-2 (Bruker, 2010)' _computing_cell_refinement 'SAINT v.7.68a (Bruker, 2010)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXTL v.6.12 (Sheldrick, 2008)' _computing_structure_refinement SHELXTL _computing_molecular_graphics SHELXTL _computing_publication_material SHELXTL _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^)+(0.0447P)^2^+0.1110P] 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 1527 _refine_ls_number_parameters 123 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0592 _refine_ls_R_factor_gt 0.0362 _refine_ls_wR_factor_ref 0.0953 _refine_ls_wR_factor_gt 0.0845 _refine_ls_goodness_of_fit_ref 1.073 _refine_ls_restrained_S_all 1.073 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.217 _refine_diff_density_min -0.170 _refine_diff_density_rms 0.051 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 0.61982(10) 0.1398(2) 0.60875(11) 0.0580(4) Uani 1 1 d . . . H1 H 0.564(3) 0.009(5) 0.598(2) 0.145(11) Uiso 1 1 d . . . O2 O 0.50989(11) 0.1890(2) 0.40857(11) 0.0613(4) Uani 1 1 d . . . O3 O 0.78530(9) 0.41299(19) 0.72702(9) 0.0499(3) Uani 1 1 d . . . O4 O 0.90425(11) 0.2181(2) 0.66665(11) 0.0630(4) Uani 1 1 d . . . C1 C 0.65382(13) 0.4367(2) 0.50763(14) 0.0415(4) Uani 1 1 d . . . C2 C 0.74612(13) 0.5134(3) 0.61114(13) 0.0438(4) Uani 1 1 d . . . C3 C 0.79868(15) 0.6961(3) 0.60500(17) 0.0549(5) Uani 1 1 d . . . H3 H 0.8608 0.7469 0.6772 0.066 Uiso 1 1 calc R . . C4 C 0.76147(17) 0.8058(3) 0.49423(18) 0.0592(5) Uani 1 1 d . . . H4 H 0.7984 0.9316 0.4900 0.071 Uiso 1 1 calc R . . C5 C 0.67148(16) 0.7338(3) 0.39042(17) 0.0564(5) Uani 1 1 d . . . H5 H 0.6459 0.8088 0.3139 0.068 Uiso 1 1 calc R . . C6 C 0.61817(14) 0.5519(3) 0.39757(15) 0.0486(4) Uani 1 1 d . . . H6 H 0.5552 0.5036 0.3252 0.058 Uiso 1 1 calc R . . C7 C 0.59022(14) 0.2436(3) 0.50651(14) 0.0434(4) Uani 1 1 d . . . C8 C 0.86545(15) 0.2613(3) 0.74397(15) 0.0489(4) Uani 1 1 d . . . C9 C 0.89571(18) 0.1645(4) 0.86890(17) 0.0719(6) Uani 1 1 d . . . H7 H 0.9498 0.0505 0.8776 0.108 Uiso 1 1 calc R . . H8 H 0.8243 0.1130 0.8768 0.108 Uiso 1 1 calc R . . H9 H 0.9330 0.2658 0.9350 0.108 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 0.0575(8) 0.0625(9) 0.0438(7) 0.0109(6) 0.0080(6) -0.0087(6) O2 0.0634(8) 0.0663(9) 0.0407(7) 0.0003(6) 0.0046(6) -0.0166(7) O3 0.0481(7) 0.0640(8) 0.0329(6) -0.0017(5) 0.0103(5) 0.0037(6) O4 0.0632(8) 0.0820(10) 0.0452(7) 0.0084(6) 0.0222(6) 0.0189(7) C1 0.0397(9) 0.0464(10) 0.0373(9) -0.0011(7) 0.0133(7) 0.0040(8) C2 0.0424(9) 0.0515(11) 0.0355(8) -0.0011(8) 0.0125(7) 0.0044(8) C3 0.0475(10) 0.0586(12) 0.0517(11) -0.0087(9) 0.0114(8) -0.0054(9) C4 0.0591(12) 0.0511(11) 0.0662(12) 0.0026(9) 0.0223(10) -0.0048(9) C5 0.0567(11) 0.0573(12) 0.0510(10) 0.0101(9) 0.0158(9) 0.0031(9) C6 0.0450(10) 0.0557(12) 0.0409(9) 0.0009(8) 0.0116(7) 0.0012(8) C7 0.0408(9) 0.0516(11) 0.0346(9) -0.0002(8) 0.0107(7) 0.0028(8) C8 0.0402(10) 0.0623(12) 0.0368(9) 0.0002(8) 0.0065(8) -0.0028(8) C9 0.0670(12) 0.0985(17) 0.0463(11) 0.0220(10) 0.0172(9) 0.0118(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 C7 1.2832(19) . ? O1 H1 1.07(3) . ? O2 C7 1.2359(18) . ? O3 C8 1.362(2) . ? O3 C2 1.3953(18) . ? O4 C8 1.194(2) . ? C1 C2 1.390(2) . ? C1 C6 1.391(2) . ? C1 C7 1.483(2) . ? C2 C3 1.373(2) . ? C3 C4 1.378(3) . ? C3 H3 0.9500 . ? C4 C5 1.367(3) . ? C4 H4 0.9500 . ? C5 C6 1.376(2) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C8 C9 1.481(2) . ? C9 H7 0.9800 . ? C9 H8 0.9800 . ? C9 H9 0.9800 . ? 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 C7 O1 H1 111.4(14) . . ? C8 O3 C2 116.56(12) . . ? C2 C1 C6 117.07(15) . . ? C2 C1 C7 124.95(14) . . ? C6 C1 C7 117.98(14) . . ? C3 C2 C1 121.26(15) . . ? C3 C2 O3 117.32(14) . . ? C1 C2 O3 121.35(15) . . ? C2 C3 C4 120.12(16) . . ? C2 C3 H3 119.9 . . ? C4 C3 H3 119.9 . . ? C5 C4 C3 120.06(18) . . ? C5 C4 H4 120.0 . . ? C3 C4 H4 120.0 . . ? C4 C5 C6 119.57(16) . . ? C4 C5 H5 120.2 . . ? C6 C5 H5 120.2 . . ? C5 C6 C1 121.91(15) . . ? C5 C6 H6 119.0 . . ? C1 C6 H6 119.0 . . ? O2 C7 O1 122.07(15) . . ? O2 C7 C1 119.47(14) . . ? O1 C7 C1 118.45(14) . . ? O4 C8 O3 122.83(15) . . ? O4 C8 C9 126.66(17) . . ? O3 C8 C9 110.50(15) . . ? C8 C9 H7 109.5 . . ? C8 C9 H8 109.5 . . ? H7 C9 H8 109.5 . . ? C8 C9 H9 109.5 . . ? H7 C9 H9 109.5 . . ? H8 C9 H9 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 C6 C1 C2 C3 0.7(2) . . . . ? C7 C1 C2 C3 -178.55(15) . . . . ? C6 C1 C2 O3 177.57(13) . . . . ? C7 C1 C2 O3 -1.7(2) . . . . ? C8 O3 C2 C3 -97.37(18) . . . . ? C8 O3 C2 C1 85.64(18) . . . . ? C1 C2 C3 C4 -1.0(3) . . . . ? O3 C2 C3 C4 -178.01(16) . . . . ? C2 C3 C4 C5 0.5(3) . . . . ? C3 C4 C5 C6 0.3(3) . . . . ? C4 C5 C6 C1 -0.6(3) . . . . ? C2 C1 C6 C5 0.1(2) . . . . ? C7 C1 C6 C5 179.43(15) . . . . ? C2 C1 C7 O2 -179.37(15) . . . . ? C6 C1 C7 O2 1.4(2) . . . . ? C2 C1 C7 O1 1.6(2) . . . . ? C6 C1 C7 O1 -177.67(14) . . . . ? C2 O3 C8 O4 2.4(2) . . . . ? C2 O3 C8 C9 -178.09(15) . . . . ?