# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_C:\frames _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 2_36%CO2 _chemical_melting_point ? _chemical_formula_moiety 'C12 H10 O2, 0.055(C O2)' _chemical_formula_sum 'C12.05 H10 O2.11' _chemical_formula_weight 188.55 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 Trigonal _symmetry_space_group_name_H-M 'R -3' _symmetry_space_group_name_Hall '-R 3' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z' '-x+y, -x, z' 'x+2/3, y+1/3, z+1/3' '-y+2/3, x-y+1/3, z+1/3' '-x+y+2/3, -x+1/3, z+1/3' 'x+1/3, y+2/3, z+2/3' '-y+1/3, x-y+2/3, z+2/3' '-x+y+1/3, -x+2/3, z+2/3' '-x, -y, -z' 'y, -x+y, -z' 'x-y, x, -z' '-x+2/3, -y+1/3, -z+1/3' 'y+2/3, -x+y+1/3, -z+1/3' 'x-y+2/3, x+1/3, -z+1/3' '-x+1/3, -y+2/3, -z+2/3' 'y+1/3, -x+y+2/3, -z+2/3' 'x-y+1/3, x+2/3, -z+2/3' _cell_length_a 29.000(4) _cell_length_b 29.000(4) _cell_length_c 5.8505(8) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 4260.9(10) _cell_formula_units_Z 18 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 1058 _cell_measurement_theta_min 24.07 _cell_measurement_theta_max 2.43 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.323 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1785 _exptl_absorpt_coefficient_mu 0.090 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9648 _exptl_absorpt_correction_T_max 0.9910 _exptl_absorpt_process_details 'SADABS (Bruker, 2009)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 Duo CCD Area Detector' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10595 _diffrn_reflns_av_R_equivalents 0.1032 _diffrn_reflns_av_sigmaI/netI 0.0835 _diffrn_reflns_limit_h_min -37 _diffrn_reflns_limit_h_max 37 _diffrn_reflns_limit_k_min -37 _diffrn_reflns_limit_k_max 37 _diffrn_reflns_limit_l_min -7 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_theta_min 1.40 _diffrn_reflns_theta_max 27.46 _reflns_number_total 2149 _reflns_number_gt 1303 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker, 2009)' _computing_cell_refinement 'SAINT (Bruker, 2009)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL (Sheldrick, 2008)' _computing_molecular_graphics 'X-Seed (Barbour 2001)' _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^)+(0.0349P)^2^+4.3399P] 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 2149 _refine_ls_number_parameters 136 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1030 _refine_ls_R_factor_gt 0.0522 _refine_ls_wR_factor_ref 0.1278 _refine_ls_wR_factor_gt 0.1072 _refine_ls_goodness_of_fit_ref 1.026 _refine_ls_restrained_S_all 1.026 _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 C1 C 0.47883(8) 0.59191(8) 0.6654(4) 0.0193(5) Uani 1 1 d . . . C2 C 0.48140(8) 0.64062(8) 0.6914(4) 0.0214(5) Uani 1 1 d . . . H2 H 0.4985 0.6622 0.8210 0.026 Uiso 1 1 calc R . . C3 C 0.45884(8) 0.65751(8) 0.5263(4) 0.0204(5) Uani 1 1 d . . . H3 H 0.4601 0.6907 0.5426 0.024 Uiso 1 1 calc R . . O4 O 0.40973(6) 0.63934(6) 0.1703(3) 0.0216(4) Uani 1 1 d . . . C4 C 0.43450(8) 0.62576(8) 0.3377(4) 0.0182(5) Uani 1 1 d . . . H4 H 0.4182(11) 0.6742(12) 0.184(5) 0.052(9) Uiso 1 1 d . . . C5 C 0.43271(8) 0.57727(8) 0.3115(4) 0.0203(5) Uani 1 1 d . . . H5 H 0.4165 0.5560 0.1802 0.024 Uiso 1 1 calc R . . C6 C 0.45470(9) 0.56024(9) 0.4775(4) 0.0224(5) Uani 1 1 d . . . H6 H 0.4532 0.5269 0.4622 0.027 Uiso 1 1 calc R . . O7 O 0.49793(6) 0.57409(6) 0.8455(3) 0.0237(4) Uani 1 1 d . . . C8 C 0.54483(8) 0.57288(8) 0.8141(4) 0.0187(5) Uani 1 1 d . . . C9 C 0.57582(8) 0.59068(8) 0.6199(4) 0.0204(5) Uani 1 1 d . . . H9 H 0.5649 0.6034 0.4931 0.025 Uiso 1 1 calc R . . C10 C 0.62343(9) 0.58967(9) 0.6127(4) 0.0252(5) Uani 1 1 d . . . H10 H 0.6453 0.6021 0.4805 0.030 Uiso 1 1 calc R . . C11 C 0.63894(9) 0.57066(9) 0.7964(4) 0.0251(5) Uani 1 1 d . . . H11 H 0.6713 0.5700 0.7904 0.030 Uiso 1 1 calc R . . C12 C 0.60703(9) 0.55251(9) 0.9896(4) 0.0239(5) Uani 1 1 d . . . H12 H 0.6174 0.5390 1.1152 0.029 Uiso 1 1 calc R . . C13 C 0.56028(8) 0.55394(8) 1.0002(4) 0.0216(5) Uani 1 1 d . . . H13 H 0.5388 0.5421 1.1336 0.026 Uiso 1 1 calc R . . C14 C 0.3333 0.6667 0.6667 0.079(9) Uani 0.32 6 d SP . . O15 O 0.3333 0.6667 0.468(2) 0.081(4) Uani 0.32 3 d SP . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0152(11) 0.0205(11) 0.0227(12) 0.0054(10) 0.0045(9) 0.0092(9) C2 0.0183(11) 0.0192(11) 0.0248(13) -0.0022(10) 0.0001(10) 0.0080(9) C3 0.0167(11) 0.0142(10) 0.0281(13) 0.0007(10) 0.0037(10) 0.0061(9) O4 0.0206(8) 0.0183(8) 0.0265(9) 0.0011(7) -0.0029(7) 0.0101(7) C4 0.0133(10) 0.0185(11) 0.0210(12) 0.0043(10) 0.0036(9) 0.0066(9) C5 0.0183(11) 0.0186(11) 0.0231(12) -0.0020(10) 0.0008(9) 0.0086(9) C6 0.0226(12) 0.0192(11) 0.0256(13) 0.0012(10) 0.0048(10) 0.0107(10) O7 0.0214(8) 0.0296(9) 0.0244(9) 0.0066(7) 0.0036(7) 0.0160(7) C8 0.0159(11) 0.0150(10) 0.0250(12) -0.0026(9) 0.0007(9) 0.0075(9) C9 0.0197(11) 0.0162(11) 0.0230(12) -0.0002(9) 0.0001(10) 0.0072(9) C10 0.0209(12) 0.0232(12) 0.0266(13) -0.0043(10) 0.0039(10) 0.0074(10) C11 0.0191(12) 0.0242(12) 0.0326(14) -0.0098(11) -0.0050(10) 0.0112(10) C12 0.0249(12) 0.0222(12) 0.0260(13) -0.0037(10) -0.0052(10) 0.0129(10) C13 0.0209(11) 0.0188(11) 0.0234(12) -0.0001(10) 0.0005(10) 0.0087(9) C14 0.103(16) 0.103(16) 0.032(16) 0.000 0.000 0.052(8) O15 0.097(7) 0.097(7) 0.050(8) 0.000 0.000 0.048(3) _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 C1 C6 1.378(3) . ? C1 C2 1.385(3) . ? C1 O7 1.404(3) . ? C2 C3 1.386(3) . ? C2 H2 0.9500 . ? C3 C4 1.384(3) . ? C3 H3 0.9500 . ? O4 C4 1.383(3) . ? O4 H4 0.92(3) . ? C4 C5 1.390(3) . ? C5 C6 1.381(3) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? O7 C8 1.390(2) . ? C8 C9 1.379(3) . ? C8 C13 1.390(3) . ? C9 C10 1.396(3) . ? C9 H9 0.9500 . ? C10 C11 1.382(3) . ? C10 H10 0.9500 . ? C11 C12 1.387(3) . ? C11 H11 0.9500 . ? C12 C13 1.378(3) . ? C12 H12 0.9500 . ? C13 H13 0.9500 . ? C14 O15 1.162(13) 13_566 ? C14 O15 1.162(13) . ? 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 C6 C1 C2 121.2(2) . . ? C6 C1 O7 121.04(19) . . ? C2 C1 O7 117.6(2) . . ? C1 C2 C3 119.3(2) . . ? C1 C2 H2 120.3 . . ? C3 C2 H2 120.3 . . ? C4 C3 C2 119.6(2) . . ? C4 C3 H3 120.2 . . ? C2 C3 H3 120.2 . . ? C4 O4 H4 111.2(18) . . ? O4 C4 C3 122.71(19) . . ? O4 C4 C5 116.62(19) . . ? C3 C4 C5 120.6(2) . . ? C6 C5 C4 119.6(2) . . ? C6 C5 H5 120.2 . . ? C4 C5 H5 120.2 . . ? C1 C6 C5 119.6(2) . . ? C1 C6 H6 120.2 . . ? C5 C6 H6 120.2 . . ? C8 O7 C1 118.80(16) . . ? C9 C8 O7 124.2(2) . . ? C9 C8 C13 121.0(2) . . ? O7 C8 C13 114.79(19) . . ? C8 C9 C10 118.9(2) . . ? C8 C9 H9 120.6 . . ? C10 C9 H9 120.6 . . ? C11 C10 C9 120.5(2) . . ? C11 C10 H10 119.8 . . ? C9 C10 H10 119.8 . . ? C10 C11 C12 119.8(2) . . ? C10 C11 H11 120.1 . . ? C12 C11 H11 120.1 . . ? C13 C12 C11 120.3(2) . . ? C13 C12 H12 119.8 . . ? C11 C12 H12 119.8 . . ? C12 C13 C8 119.5(2) . . ? C12 C13 H13 120.2 . . ? C8 C13 H13 120.2 . . ? 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 0.6(3) . . . . ? O7 C1 C2 C3 -174.54(18) . . . . ? C1 C2 C3 C4 -0.5(3) . . . . ? C2 C3 C4 O4 177.89(19) . . . . ? C2 C3 C4 C5 -0.4(3) . . . . ? O4 C4 C5 C6 -177.27(19) . . . . ? C3 C4 C5 C6 1.1(3) . . . . ? C2 C1 C6 C5 0.1(3) . . . . ? O7 C1 C6 C5 175.09(19) . . . . ? C4 C5 C6 C1 -0.9(3) . . . . ? C6 C1 O7 C8 75.1(3) . . . . ? C2 C1 O7 C8 -109.8(2) . . . . ? C1 O7 C8 C9 3.4(3) . . . . ? C1 O7 C8 C13 -179.09(18) . . . . ? O7 C8 C9 C10 177.06(19) . . . . ? C13 C8 C9 C10 -0.3(3) . . . . ? C8 C9 C10 C11 0.6(3) . . . . ? C9 C10 C11 C12 -0.1(3) . . . . ? C10 C11 C12 C13 -0.8(3) . . . . ? C11 C12 C13 C8 1.1(3) . . . . ? C9 C8 C13 C12 -0.6(3) . . . . ? O7 C8 C13 C12 -178.15(18) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O4 H4 O4 0.92(3) 1.79(3) 2.7006(15) 171(3) 15 _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 27.46 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.202 _refine_diff_density_min -0.274 _refine_diff_density_rms 0.057 _database_code_depnum_ccdc_archive 'CCDC 959280' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_C:\frames _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 2_73%CO2 _chemical_melting_point ? _chemical_formula_moiety 'C12 H10 O2, 0.12(C O2)' _chemical_formula_sum 'C12.12 H10 O2.24' _chemical_formula_weight 191.55 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 Trigonal _symmetry_space_group_name_H-M 'R -3' _symmetry_space_group_name_Hall '-R 3' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z' '-x+y, -x, z' 'x+2/3, y+1/3, z+1/3' '-y+2/3, x-y+1/3, z+1/3' '-x+y+2/3, -x+1/3, z+1/3' 'x+1/3, y+2/3, z+2/3' '-y+1/3, x-y+2/3, z+2/3' '-x+y+1/3, -x+2/3, z+2/3' '-x, -y, -z' 'y, -x+y, -z' 'x-y, x, -z' '-x+2/3, -y+1/3, -z+1/3' 'y+2/3, -x+y+1/3, -z+1/3' 'x-y+2/3, x+1/3, -z+1/3' '-x+1/3, -y+2/3, -z+2/3' 'y+1/3, -x+y+2/3, -z+2/3' 'x-y+1/3, x+2/3, -z+2/3' _cell_length_a 28.906(10) _cell_length_b 28.906(10) _cell_length_c 5.862(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 4242(3) _cell_formula_units_Z 18 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 1998 _cell_measurement_theta_min 2.44 _cell_measurement_theta_max 25.52 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.350 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1812 _exptl_absorpt_coefficient_mu 0.093 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9638 _exptl_absorpt_correction_T_max 0.9908 _exptl_absorpt_process_details 'SADABS (Bruker, 2009)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15769 _diffrn_reflns_av_R_equivalents 0.0961 _diffrn_reflns_av_sigmaI/netI 0.0583 _diffrn_reflns_limit_h_min -37 _diffrn_reflns_limit_h_max 37 _diffrn_reflns_limit_k_min -37 _diffrn_reflns_limit_k_max 36 _diffrn_reflns_limit_l_min -7 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_theta_min 2.44 _diffrn_reflns_theta_max 27.57 _reflns_number_total 2172 _reflns_number_gt 1407 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker, 2009)' _computing_cell_refinement 'SAINT (Bruker, 2009)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL (Sheldrick, 2008)' _computing_molecular_graphics 'X-Seed (Barbour 2001)' _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^)+(0.0701P)^2^+3.7081P] 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 SHELXL _refine_ls_extinction_coef 0.0020(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2172 _refine_ls_number_parameters 137 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0897 _refine_ls_R_factor_gt 0.0500 _refine_ls_wR_factor_ref 0.1473 _refine_ls_wR_factor_gt 0.1255 _refine_ls_goodness_of_fit_ref 1.014 _refine_ls_restrained_S_all 1.014 _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 C1 C 0.47911(8) 0.59247(8) 0.6664(3) 0.0208(4) Uani 1 1 d . . . C2 C 0.48133(8) 0.64107(8) 0.6902(3) 0.0219(5) Uani 1 1 d . . . H2 H 0.4981 0.6628 0.8199 0.026 Uiso 1 1 calc R . . C3 C 0.45893(8) 0.65808(8) 0.5238(3) 0.0218(5) Uani 1 1 d . . . H3 H 0.4602 0.6914 0.5391 0.026 Uiso 1 1 calc R . . O4 O 0.41028(6) 0.63964(6) 0.1681(2) 0.0230(4) Uani 1 1 d . . . C4 C 0.43480(7) 0.62615(8) 0.3360(3) 0.0192(4) Uani 1 1 d . . . H4 H 0.4178(12) 0.6719(13) 0.181(5) 0.058(9) Uiso 1 1 d . . . C5 C 0.43326(8) 0.57762(8) 0.3110(4) 0.0220(5) Uani 1 1 d . . . H5 H 0.4174 0.5563 0.1795 0.026 Uiso 1 1 calc R . . C6 C 0.45502(8) 0.56051(8) 0.4792(4) 0.0232(5) Uani 1 1 d . . . H6 H 0.4533 0.5270 0.4654 0.028 Uiso 1 1 calc R . . O7 O 0.49796(5) 0.57474(6) 0.8454(2) 0.0248(4) Uani 1 1 d . . . C8 C 0.54468(8) 0.57309(8) 0.8162(3) 0.0211(4) Uani 1 1 d . . . C9 C 0.57596(8) 0.59068(8) 0.6223(3) 0.0219(5) Uani 1 1 d . . . H9 H 0.5653 0.6036 0.4953 0.026 Uiso 1 1 calc R . . C10 C 0.62340(8) 0.58920(8) 0.6160(4) 0.0265(5) Uani 1 1 d . . . H10 H 0.6454 0.6015 0.4840 0.032 Uiso 1 1 calc R . . C11 C 0.63887(8) 0.57013(8) 0.7994(4) 0.0265(5) Uani 1 1 d . . . H11 H 0.6712 0.5692 0.7938 0.032 Uiso 1 1 calc R . . C12 C 0.60676(8) 0.55242(8) 0.9919(4) 0.0260(5) Uani 1 1 d . . . H12 H 0.6171 0.5390 1.1180 0.031 Uiso 1 1 calc R . . C13 C 0.55997(8) 0.55416(8) 1.0020(4) 0.0224(5) Uani 1 1 d . . . H13 H 0.5384 0.5425 1.1352 0.027 Uiso 1 1 calc R . . C14 C 0.3333 0.6667 0.6667 0.041(2) Uani 0.73 6 d SP . . O15 O 0.3333 0.6667 0.4708(8) 0.0588(13) Uani 0.73 3 d SP . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0161(9) 0.0218(10) 0.0246(11) 0.0051(8) 0.0035(8) 0.0095(8) C2 0.0175(9) 0.0206(10) 0.0260(11) -0.0002(8) 0.0000(8) 0.0083(8) C3 0.0189(10) 0.0167(9) 0.0290(11) 0.0000(8) 0.0024(8) 0.0082(8) O4 0.0212(7) 0.0181(7) 0.0301(8) 0.0018(6) -0.0017(6) 0.0101(6) C4 0.0152(9) 0.0190(9) 0.0229(10) 0.0029(8) 0.0022(8) 0.0082(8) C5 0.0194(10) 0.0193(10) 0.0270(11) -0.0004(8) 0.0016(8) 0.0094(8) C6 0.0207(10) 0.0172(9) 0.0327(12) 0.0013(9) 0.0034(9) 0.0102(8) O7 0.0204(7) 0.0302(8) 0.0284(8) 0.0064(6) 0.0043(6) 0.0163(6) C8 0.0159(9) 0.0173(9) 0.0295(11) -0.0013(8) 0.0007(8) 0.0080(8) C9 0.0190(10) 0.0173(9) 0.0266(11) -0.0008(8) 0.0010(8) 0.0070(8) C10 0.0225(10) 0.0248(11) 0.0305(12) -0.0036(9) 0.0026(9) 0.0106(9) C11 0.0187(10) 0.0253(11) 0.0363(12) -0.0081(9) -0.0035(9) 0.0116(9) C12 0.0236(11) 0.0230(10) 0.0317(12) -0.0041(9) -0.0054(9) 0.0119(9) C13 0.0216(10) 0.0179(9) 0.0263(11) -0.0017(8) -0.0008(8) 0.0088(8) C14 0.042(3) 0.042(3) 0.038(5) 0.000 0.000 0.0210(16) O15 0.067(2) 0.067(2) 0.043(3) 0.000 0.000 0.0333(11) _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 C1 C6 1.378(3) . ? C1 C2 1.381(3) . ? C1 O7 1.393(2) . ? C2 C3 1.390(3) . ? C2 H2 0.9500 . ? C3 C4 1.381(3) . ? C3 H3 0.9500 . ? O4 C4 1.378(2) . ? O4 H4 0.85(3) . ? C4 C5 1.389(3) . ? C5 C6 1.387(3) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? O7 C8 1.386(2) . ? C8 C9 1.381(3) . ? C8 C13 1.387(3) . ? C9 C10 1.394(3) . ? C9 H9 0.9500 . ? C10 C11 1.381(3) . ? C10 H10 0.9500 . ? C11 C12 1.386(3) . ? C11 H11 0.9500 . ? C12 C13 1.380(3) . ? C12 H12 0.9500 . ? C13 H13 0.9500 . ? C14 O15 1.148(5) 13_566 ? C14 O15 1.148(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 C6 C1 C2 120.90(18) . . ? C6 C1 O7 120.85(18) . . ? C2 C1 O7 118.05(18) . . ? C1 C2 C3 119.74(19) . . ? C1 C2 H2 120.1 . . ? C3 C2 H2 120.1 . . ? C4 C3 C2 119.48(18) . . ? C4 C3 H3 120.3 . . ? C2 C3 H3 120.3 . . ? C4 O4 H4 111(2) . . ? O4 C4 C3 122.65(18) . . ? O4 C4 C5 116.69(18) . . ? C3 C4 C5 120.64(18) . . ? C6 C5 C4 119.62(19) . . ? C6 C5 H5 120.2 . . ? C4 C5 H5 120.2 . . ? C1 C6 C5 119.61(18) . . ? C1 C6 H6 120.2 . . ? C5 C6 H6 120.2 . . ? C8 O7 C1 119.12(16) . . ? C9 C8 O7 124.00(18) . . ? C9 C8 C13 120.82(18) . . ? O7 C8 C13 115.13(17) . . ? C8 C9 C10 118.92(19) . . ? C8 C9 H9 120.5 . . ? C10 C9 H9 120.5 . . ? C11 C10 C9 120.8(2) . . ? C11 C10 H10 119.6 . . ? C9 C10 H10 119.6 . . ? C10 C11 C12 119.4(2) . . ? C10 C11 H11 120.3 . . ? C12 C11 H11 120.3 . . ? C13 C12 C11 120.6(2) . . ? C13 C12 H12 119.7 . . ? C11 C12 H12 119.7 . . ? C12 C13 C8 119.5(2) . . ? C12 C13 H13 120.2 . . ? C8 C13 H13 120.2 . . ? 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 0.1(3) . . . . ? O7 C1 C2 C3 -174.72(17) . . . . ? C1 C2 C3 C4 -0.2(3) . . . . ? C2 C3 C4 O4 177.85(17) . . . . ? C2 C3 C4 C5 -0.7(3) . . . . ? O4 C4 C5 C6 -177.04(17) . . . . ? C3 C4 C5 C6 1.6(3) . . . . ? C2 C1 C6 C5 0.8(3) . . . . ? O7 C1 C6 C5 175.47(18) . . . . ? C4 C5 C6 C1 -1.6(3) . . . . ? C6 C1 O7 C8 74.8(2) . . . . ? C2 C1 O7 C8 -110.4(2) . . . . ? C1 O7 C8 C9 3.5(3) . . . . ? C1 O7 C8 C13 -179.06(17) . . . . ? O7 C8 C9 C10 177.22(18) . . . . ? C13 C8 C9 C10 -0.1(3) . . . . ? C8 C9 C10 C11 0.5(3) . . . . ? C9 C10 C11 C12 -0.2(3) . . . . ? C10 C11 C12 C13 -0.6(3) . . . . ? C11 C12 C13 C8 1.0(3) . . . . ? C9 C8 C13 C12 -0.6(3) . . . . ? O7 C8 C13 C12 -178.17(17) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O4 H4 O4 0.85(3) 1.86(3) 2.7008(17) 172(3) 15 _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.57 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.246 _refine_diff_density_min -0.300 _refine_diff_density_rms 0.060 _database_code_depnum_ccdc_archive 'CCDC 959281' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_C:\frames _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 2_CO2 _chemical_melting_point ? _chemical_formula_moiety 'C12 H10 O2, 0.16(C O2)' _chemical_formula_sum 'C12.17 H10 O2.33' _chemical_formula_weight 193.53 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 Trigonal _symmetry_space_group_name_H-M 'R -3' _symmetry_space_group_name_Hall '-R 3' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z' '-x+y, -x, z' 'x+2/3, y+1/3, z+1/3' '-y+2/3, x-y+1/3, z+1/3' '-x+y+2/3, -x+1/3, z+1/3' 'x+1/3, y+2/3, z+2/3' '-y+1/3, x-y+2/3, z+2/3' '-x+y+1/3, -x+2/3, z+2/3' '-x, -y, -z' 'y, -x+y, -z' 'x-y, x, -z' '-x+2/3, -y+1/3, -z+1/3' 'y+2/3, -x+y+1/3, -z+1/3' 'x-y+2/3, x+1/3, -z+1/3' '-x+1/3, -y+2/3, -z+2/3' 'y+1/3, -x+y+2/3, -z+2/3' 'x-y+1/3, x+2/3, -z+2/3' _cell_length_a 28.908(6) _cell_length_b 28.908(6) _cell_length_c 5.8899(12) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 4262.6(15) _cell_formula_units_Z 18 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 4008 _cell_measurement_theta_min 2.44 _cell_measurement_theta_max 28.68 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.357 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1830 _exptl_absorpt_coefficient_mu 0.094 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9635 _exptl_absorpt_correction_T_max 0.9925 _exptl_absorpt_process_details 'SADABS (Bruker, 2009)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 Duo CCD Area Detector' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16014 _diffrn_reflns_av_R_equivalents 0.0435 _diffrn_reflns_av_sigmaI/netI 0.0274 _diffrn_reflns_limit_h_min -38 _diffrn_reflns_limit_h_max 38 _diffrn_reflns_limit_k_min -37 _diffrn_reflns_limit_k_max 38 _diffrn_reflns_limit_l_min -7 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_theta_min 1.41 _diffrn_reflns_theta_max 28.26 _reflns_number_total 2294 _reflns_number_gt 1820 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker, 2009)' _computing_cell_refinement 'SAINT (Bruker, 2009)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL (Sheldrick, 2008)' _computing_molecular_graphics 'X-Seed (Barbour 2001)' _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^)+(0.0452P)^2^+6.1732P] 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 2294 _refine_ls_number_parameters 136 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0537 _refine_ls_R_factor_gt 0.0393 _refine_ls_wR_factor_ref 0.1100 _refine_ls_wR_factor_gt 0.1012 _refine_ls_goodness_of_fit_ref 1.032 _refine_ls_restrained_S_all 1.032 _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 C1 C 0.47927(5) 0.59293(5) 0.6668(2) 0.0189(3) Uani 1 1 d . . . C2 C 0.48158(5) 0.64175(5) 0.6892(2) 0.0201(3) Uani 1 1 d . . . H2 H 0.4984 0.6637 0.8177 0.024 Uiso 1 1 calc R . . C3 C 0.45906(5) 0.65861(5) 0.5226(2) 0.0194(3) Uani 1 1 d . . . H3 H 0.4601 0.6919 0.5375 0.023 Uiso 1 1 calc R . . O4 O 0.41069(4) 0.63989(4) 0.16603(16) 0.0200(2) Uani 1 1 d . . . C4 C 0.43505(5) 0.62643(5) 0.3347(2) 0.0171(3) Uani 1 1 d . . . H4 H 0.4171(7) 0.6721(8) 0.182(3) 0.038(5) Uiso 1 1 d . . . C5 C 0.43342(5) 0.57765(5) 0.3112(2) 0.0197(3) Uani 1 1 d . . . H5 H 0.4174 0.5561 0.1809 0.024 Uiso 1 1 calc R . . C6 C 0.45527(5) 0.56066(5) 0.4789(2) 0.0211(3) Uani 1 1 d . . . H6 H 0.4538 0.5272 0.4653 0.025 Uiso 1 1 calc R . . O7 O 0.49804(4) 0.57522(4) 0.84626(16) 0.0227(2) Uani 1 1 d . . . C8 C 0.54465(5) 0.57339(5) 0.8176(2) 0.0181(3) Uani 1 1 d . . . C9 C 0.57604(5) 0.59064(5) 0.6233(2) 0.0200(3) Uani 1 1 d . . . H9 H 0.5655 0.6034 0.4963 0.024 Uiso 1 1 calc R . . C10 C 0.62336(5) 0.58882(6) 0.6180(2) 0.0242(3) Uani 1 1 d . . . H10 H 0.6453 0.6008 0.4865 0.029 Uiso 1 1 calc R . . C11 C 0.63882(5) 0.56978(6) 0.8020(3) 0.0249(3) Uani 1 1 d . . . H11 H 0.6711 0.5687 0.7967 0.030 Uiso 1 1 calc R . . C12 C 0.60662(6) 0.55226(6) 0.9942(3) 0.0241(3) Uani 1 1 d . . . H12 H 0.6168 0.5388 1.1201 0.029 Uiso 1 1 calc R . . C13 C 0.55969(5) 0.55430(5) 1.0034(2) 0.0207(3) Uani 1 1 d . . . H13 H 0.5380 0.5427 1.1358 0.025 Uiso 1 1 calc R . . C14 C 0.3333 0.6667 0.6667 0.0302(8) Uani 1 6 d S . . O15 O 0.3333 0.6667 0.4717(4) 0.0446(5) Uani 1 3 d S . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0153(6) 0.0206(6) 0.0210(6) 0.0042(5) 0.0037(5) 0.0091(5) C2 0.0168(6) 0.0194(6) 0.0222(7) -0.0008(5) 0.0009(5) 0.0077(5) C3 0.0179(6) 0.0153(6) 0.0243(7) -0.0003(5) 0.0013(5) 0.0079(5) O4 0.0200(5) 0.0168(5) 0.0237(5) 0.0005(4) -0.0025(4) 0.0095(4) C4 0.0131(6) 0.0167(6) 0.0201(6) 0.0018(5) 0.0023(5) 0.0066(5) C5 0.0170(6) 0.0180(6) 0.0227(7) -0.0027(5) 0.0005(5) 0.0076(5) C6 0.0206(6) 0.0168(6) 0.0276(7) -0.0001(5) 0.0032(5) 0.0106(5) O7 0.0204(5) 0.0294(5) 0.0232(5) 0.0060(4) 0.0040(4) 0.0162(4) C8 0.0161(6) 0.0151(6) 0.0227(6) -0.0019(5) -0.0002(5) 0.0075(5) C9 0.0194(6) 0.0171(6) 0.0214(7) -0.0005(5) 0.0008(5) 0.0076(5) C10 0.0195(7) 0.0232(7) 0.0266(7) -0.0041(6) 0.0029(5) 0.0081(6) C11 0.0181(6) 0.0247(7) 0.0330(8) -0.0095(6) -0.0047(6) 0.0116(6) C12 0.0233(7) 0.0217(7) 0.0278(7) -0.0036(5) -0.0061(6) 0.0116(6) C13 0.0196(6) 0.0176(6) 0.0225(7) -0.0007(5) -0.0008(5) 0.0074(5) C14 0.0281(12) 0.0281(12) 0.034(2) 0.000 0.000 0.0141(6) O15 0.0517(9) 0.0517(9) 0.0305(12) 0.000 0.000 0.0259(4) _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 C1 C2 1.3857(19) . ? C1 C6 1.3890(19) . ? C1 O7 1.3968(16) . ? C2 C3 1.3934(19) . ? C2 H2 0.9500 . ? C3 C4 1.3883(18) . ? C3 H3 0.9500 . ? O4 C4 1.3811(15) . ? O4 H4 0.86(2) . ? C4 C5 1.3938(18) . ? C5 C6 1.3878(19) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? O7 C8 1.3848(16) . ? C8 C9 1.3890(19) . ? C8 C13 1.3898(19) . ? C9 C10 1.3954(19) . ? C9 H9 0.9500 . ? C10 C11 1.386(2) . ? C10 H10 0.9500 . ? C11 C12 1.391(2) . ? C11 H11 0.9500 . ? C12 C13 1.3881(19) . ? C12 H12 0.9500 . ? C13 H13 0.9500 . ? C14 O15 1.149(2) 13_566 ? C14 O15 1.149(2) . ? 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 C2 C1 C6 120.88(12) . . ? C2 C1 O7 118.14(12) . . ? C6 C1 O7 120.80(12) . . ? C1 C2 C3 119.75(12) . . ? C1 C2 H2 120.1 . . ? C3 C2 H2 120.1 . . ? C4 C3 C2 119.46(12) . . ? C4 C3 H3 120.3 . . ? C2 C3 H3 120.3 . . ? C4 O4 H4 111.2(13) . . ? O4 C4 C3 122.63(12) . . ? O4 C4 C5 116.72(11) . . ? C3 C4 C5 120.63(12) . . ? C6 C5 C4 119.76(12) . . ? C6 C5 H5 120.1 . . ? C4 C5 H5 120.1 . . ? C5 C6 C1 119.51(12) . . ? C5 C6 H6 120.2 . . ? C1 C6 H6 120.2 . . ? C8 O7 C1 119.04(10) . . ? O7 C8 C9 124.07(12) . . ? O7 C8 C13 115.02(12) . . ? C9 C8 C13 120.89(12) . . ? C8 C9 C10 118.81(13) . . ? C8 C9 H9 120.6 . . ? C10 C9 H9 120.6 . . ? C11 C10 C9 120.93(13) . . ? C11 C10 H10 119.5 . . ? C9 C10 H10 119.5 . . ? C10 C11 C12 119.42(13) . . ? C10 C11 H11 120.3 . . ? C12 C11 H11 120.3 . . ? C13 C12 C11 120.45(13) . . ? C13 C12 H12 119.8 . . ? C11 C12 H12 119.8 . . ? C12 C13 C8 119.51(13) . . ? C12 C13 H13 120.2 . . ? C8 C13 H13 120.2 . . ? O15 C14 O15 179.991(2) 13_566 . ? 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) . . . . ? O7 C1 C2 C3 -174.48(11) . . . . ? C1 C2 C3 C4 -0.68(19) . . . . ? C2 C3 C4 O4 178.22(11) . . . . ? C2 C3 C4 C5 -0.16(19) . . . . ? O4 C4 C5 C6 -177.49(12) . . . . ? C3 C4 C5 C6 0.99(19) . . . . ? C4 C5 C6 C1 -1.0(2) . . . . ? C2 C1 C6 C5 0.1(2) . . . . ? O7 C1 C6 C5 175.18(12) . . . . ? C2 C1 O7 C8 -110.44(13) . . . . ? C6 C1 O7 C8 74.38(16) . . . . ? C1 O7 C8 C9 3.25(18) . . . . ? C1 O7 C8 C13 -178.82(11) . . . . ? O7 C8 C9 C10 177.40(12) . . . . ? C13 C8 C9 C10 -0.41(19) . . . . ? C8 C9 C10 C11 0.5(2) . . . . ? C9 C10 C11 C12 0.0(2) . . . . ? C10 C11 C12 C13 -0.7(2) . . . . ? C11 C12 C13 C8 0.8(2) . . . . ? O7 C8 C13 C12 -178.26(12) . . . . ? C9 C8 C13 C12 -0.3(2) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O4 H4 O4 0.86(2) 1.86(2) 2.7076(11) 169.5(18) 15 _diffrn_measured_fraction_theta_max 0.975 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.245 _refine_diff_density_min -0.222 _refine_diff_density_rms 0.045 _database_code_depnum_ccdc_archive 'CCDC 959282' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_C:\frames _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 2_vac_100K _chemical_melting_point ? _chemical_formula_moiety 'C12 H10 O2' _chemical_formula_sum 'C12 H10 O2' _chemical_formula_weight 186.20 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 Trigonal _symmetry_space_group_name_H-M 'R -3' _symmetry_space_group_name_Hall '-R 3' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z' '-x+y, -x, z' 'x+2/3, y+1/3, z+1/3' '-y+2/3, x-y+1/3, z+1/3' '-x+y+2/3, -x+1/3, z+1/3' 'x+1/3, y+2/3, z+2/3' '-y+1/3, x-y+2/3, z+2/3' '-x+y+1/3, -x+2/3, z+2/3' '-x, -y, -z' 'y, -x+y, -z' 'x-y, x, -z' '-x+2/3, -y+1/3, -z+1/3' 'y+2/3, -x+y+1/3, -z+1/3' 'x-y+2/3, x+1/3, -z+1/3' '-x+1/3, -y+2/3, -z+2/3' 'y+1/3, -x+y+2/3, -z+2/3' 'x-y+1/3, x+2/3, -z+2/3' _cell_length_a 29.0785(18) _cell_length_b 29.0785(18) _cell_length_c 5.8540(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 4286.7(5) _cell_formula_units_Z 18 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 6234 _cell_measurement_theta_min 2.80 _cell_measurement_theta_max 33.15 _exptl_crystal_description rod _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.298 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1764 _exptl_absorpt_coefficient_mu 0.088 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9657 _exptl_absorpt_correction_T_max 0.9826 _exptl_absorpt_process_details 'SADABS (Bruker, 2009)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 Duo CCD Area Detector' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 22841 _diffrn_reflns_av_R_equivalents 0.0351 _diffrn_reflns_av_sigmaI/netI 0.0236 _diffrn_reflns_limit_h_min -44 _diffrn_reflns_limit_h_max 45 _diffrn_reflns_limit_k_min -44 _diffrn_reflns_limit_k_max 45 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 2.43 _diffrn_reflns_theta_max 33.86 _reflns_number_total 3691 _reflns_number_gt 2923 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker, 2009)' _computing_cell_refinement 'SAINT (Bruker, 2009)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL (Sheldrick, 2008)' _computing_molecular_graphics 'X-Seed (Barbour 2001)' _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^)+(0.0586P)^2^+3.0600P] 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 3691 _refine_ls_number_parameters 131 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0577 _refine_ls_R_factor_gt 0.0430 _refine_ls_wR_factor_ref 0.1194 _refine_ls_wR_factor_gt 0.1092 _refine_ls_goodness_of_fit_ref 1.035 _refine_ls_restrained_S_all 1.035 _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 C1 C 0.07500(3) 0.22066(3) 0.49991(15) 0.01856(16) Uani 1 1 d . . . C2 C 0.02631(4) 0.17445(3) 0.52510(15) 0.02006(17) Uani 1 1 d . . . H2 H 0.0047 0.1700 0.6544 0.024 Uiso 1 1 calc R . . C3 C 0.00921(3) 0.13465(3) 0.36037(15) 0.01988(16) Uani 1 1 d . . . H3 H -0.0239 0.1028 0.3771 0.024 Uiso 1 1 calc R . . O4 O 0.02742(3) 0.10351(3) 0.00523(12) 0.02113(14) Uani 1 1 d . . . C4 C 0.04111(3) 0.14198(3) 0.17101(14) 0.01720(15) Uani 1 1 d . . . H4 H -0.0060(6) 0.0775(6) 0.017(3) 0.042(4) Uiso 1 1 d . . . C5 C 0.08962(3) 0.18871(3) 0.14432(16) 0.02025(17) Uani 1 1 d . . . H5 H 0.1108 0.1936 0.0131 0.024 Uiso 1 1 calc R . . C6 C 0.10683(3) 0.22811(3) 0.31059(16) 0.02117(17) Uani 1 1 d . . . H6 H 0.1401 0.2598 0.2948 0.025 Uiso 1 1 calc R . . O7 O 0.09285(3) 0.25741(3) 0.67773(11) 0.02255(15) Uani 1 1 d . . . C8 C 0.09376(3) 0.30501(3) 0.64737(14) 0.01727(15) Uani 1 1 d . . . C9 C 0.07596(3) 0.31831(4) 0.45127(15) 0.01993(16) Uani 1 1 d . . . H9 H 0.0634 0.2948 0.3243 0.024 Uiso 1 1 calc R . . C10 C 0.07681(4) 0.36674(4) 0.44416(17) 0.02430(19) Uani 1 1 d . . . H10 H 0.0643 0.3760 0.3119 0.029 Uiso 1 1 calc R . . C11 C 0.09575(4) 0.40161(4) 0.62787(18) 0.02560(19) Uani 1 1 d . . . H11 H 0.0963 0.4345 0.6212 0.031 Uiso 1 1 calc R . . C12 C 0.11399(4) 0.38796(4) 0.82198(17) 0.02392(18) Uani 1 1 d . . . H12 H 0.1273 0.4118 0.9475 0.029 Uiso 1 1 calc R . . C13 C 0.11283(3) 0.33961(4) 0.83326(15) 0.02001(16) Uani 1 1 d . . . H13 H 0.1249 0.3302 0.9665 0.024 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 C1 0.0199(4) 0.0165(3) 0.0201(4) -0.0003(3) -0.0031(3) 0.0097(3) C2 0.0186(4) 0.0201(4) 0.0213(4) 0.0009(3) 0.0020(3) 0.0095(3) C3 0.0155(3) 0.0180(4) 0.0237(4) 0.0009(3) 0.0019(3) 0.0065(3) O4 0.0181(3) 0.0198(3) 0.0242(3) -0.0041(2) -0.0007(2) 0.0085(2) C4 0.0154(3) 0.0168(3) 0.0203(4) 0.0000(3) -0.0008(3) 0.0087(3) C5 0.0167(4) 0.0194(4) 0.0229(4) 0.0017(3) 0.0029(3) 0.0078(3) C6 0.0164(4) 0.0172(4) 0.0259(4) 0.0019(3) 0.0006(3) 0.0054(3) O7 0.0301(3) 0.0175(3) 0.0214(3) -0.0021(2) -0.0072(2) 0.0130(3) C8 0.0152(3) 0.0166(3) 0.0199(4) 0.0013(3) 0.0004(3) 0.0079(3) C9 0.0187(4) 0.0217(4) 0.0202(4) 0.0019(3) -0.0002(3) 0.0106(3) C10 0.0256(4) 0.0270(4) 0.0251(4) 0.0073(3) 0.0043(3) 0.0168(4) C11 0.0276(4) 0.0220(4) 0.0318(5) 0.0053(3) 0.0089(4) 0.0159(4) C12 0.0242(4) 0.0215(4) 0.0268(4) -0.0019(3) 0.0038(3) 0.0119(3) C13 0.0187(4) 0.0213(4) 0.0207(4) -0.0009(3) 0.0000(3) 0.0104(3) _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 C1 C2 1.3890(12) . ? C1 C6 1.3898(12) . ? C1 O7 1.3930(10) . ? C2 C3 1.3932(12) . ? C2 H2 0.9500 . ? C3 C4 1.3917(12) . ? C3 H3 0.9500 . ? O4 C4 1.3806(10) . ? O4 H4 0.886(16) . ? C4 C5 1.3942(12) . ? C5 C6 1.3917(13) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? O7 C8 1.3826(10) . ? C8 C9 1.3912(12) . ? C8 C13 1.3950(12) . ? C9 C10 1.3969(13) . ? C9 H9 0.9500 . ? C10 C11 1.3891(15) . ? C10 H10 0.9500 . ? C11 C12 1.3932(14) . ? C11 H11 0.9500 . ? C12 C13 1.3908(13) . ? C12 H12 0.9500 . ? C13 H13 0.9500 . ? 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 C2 C1 C6 120.85(8) . . ? C2 C1 O7 118.13(8) . . ? C6 C1 O7 120.84(8) . . ? C1 C2 C3 119.86(8) . . ? C1 C2 H2 120.1 . . ? C3 C2 H2 120.1 . . ? C4 C3 C2 119.37(8) . . ? C4 C3 H3 120.3 . . ? C2 C3 H3 120.3 . . ? C4 O4 H4 112.7(10) . . ? O4 C4 C3 122.39(8) . . ? O4 C4 C5 116.90(7) . . ? C3 C4 C5 120.69(8) . . ? C6 C5 C4 119.75(8) . . ? C6 C5 H5 120.1 . . ? C4 C5 H5 120.1 . . ? C1 C6 C5 119.47(8) . . ? C1 C6 H6 120.3 . . ? C5 C6 H6 120.3 . . ? C8 O7 C1 119.03(7) . . ? O7 C8 C9 124.11(8) . . ? O7 C8 C13 115.06(7) . . ? C9 C8 C13 120.81(8) . . ? C8 C9 C10 118.90(8) . . ? C8 C9 H9 120.5 . . ? C10 C9 H9 120.5 . . ? C11 C10 C9 120.90(9) . . ? C11 C10 H10 119.5 . . ? C9 C10 H10 119.5 . . ? C10 C11 C12 119.47(9) . . ? C10 C11 H11 120.3 . . ? C12 C11 H11 120.3 . . ? C13 C12 C11 120.44(9) . . ? C13 C12 H12 119.8 . . ? C11 C12 H12 119.8 . . ? C12 C13 C8 119.47(8) . . ? C12 C13 H13 120.3 . . ? C8 C13 H13 120.3 . . ? 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 0.73(13) . . . . ? O7 C1 C2 C3 -174.36(8) . . . . ? C1 C2 C3 C4 -0.52(13) . . . . ? C2 C3 C4 O4 177.85(8) . . . . ? C2 C3 C4 C5 -0.42(13) . . . . ? O4 C4 C5 C6 -177.20(8) . . . . ? C3 C4 C5 C6 1.16(13) . . . . ? C2 C1 C6 C5 0.01(13) . . . . ? O7 C1 C6 C5 174.97(8) . . . . ? C4 C5 C6 C1 -0.95(13) . . . . ? C2 C1 O7 C8 -109.20(9) . . . . ? C6 C1 O7 C8 75.71(11) . . . . ? C1 O7 C8 C9 2.53(12) . . . . ? C1 O7 C8 C13 -179.24(8) . . . . ? O7 C8 C9 C10 177.32(8) . . . . ? C13 C8 C9 C10 -0.82(13) . . . . ? C8 C9 C10 C11 0.90(14) . . . . ? C9 C10 C11 C12 -0.18(14) . . . . ? C10 C11 C12 C13 -0.62(14) . . . . ? C11 C12 C13 C8 0.70(13) . . . . ? O7 C8 C13 C12 -178.27(8) . . . . ? C9 C8 C13 C12 0.03(13) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O4 H4 O4 0.886(16) 1.824(16) 2.7018(7) 170.5(15) 12 _diffrn_measured_fraction_theta_max 0.960 _diffrn_reflns_theta_full 32.50 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.376 _refine_diff_density_min -0.378 _refine_diff_density_rms 0.065 _database_code_depnum_ccdc_archive 'CCDC 959283' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_C:\frames _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 2_vac_293K _chemical_melting_point ? _chemical_formula_moiety 'C12 H10 O2' _chemical_formula_sum 'C12 H10 O2' _chemical_formula_weight 186.20 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 Trigonal _symmetry_space_group_name_H-M 'R -3' _symmetry_space_group_name_Hall '-R 3' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z' '-x+y, -x, z' 'x+2/3, y+1/3, z+1/3' '-y+2/3, x-y+1/3, z+1/3' '-x+y+2/3, -x+1/3, z+1/3' 'x+1/3, y+2/3, z+2/3' '-y+1/3, x-y+2/3, z+2/3' '-x+y+1/3, -x+2/3, z+2/3' '-x, -y, -z' 'y, -x+y, -z' 'x-y, x, -z' '-x+2/3, -y+1/3, -z+1/3' 'y+2/3, -x+y+1/3, -z+1/3' 'x-y+2/3, x+1/3, -z+1/3' '-x+1/3, -y+2/3, -z+2/3' 'y+1/3, -x+y+2/3, -z+2/3' 'x-y+1/3, x+2/3, -z+2/3' _cell_length_a 29.2571(16) _cell_length_b 29.2571(16) _cell_length_c 5.9378(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 4401.7(4) _cell_formula_units_Z 18 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3683 _cell_measurement_theta_min 2.79 _cell_measurement_theta_max 23.83 _exptl_crystal_description rod _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.264 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1764 _exptl_absorpt_coefficient_mu 0.086 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9666 _exptl_absorpt_correction_T_max 0.9831 _exptl_absorpt_process_details 'SADABS (Bruker, 2009)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 Duo CCD Area Detector' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 22590 _diffrn_reflns_av_R_equivalents 0.0418 _diffrn_reflns_av_sigmaI/netI 0.0290 _diffrn_reflns_limit_h_min -42 _diffrn_reflns_limit_h_max 44 _diffrn_reflns_limit_k_min -43 _diffrn_reflns_limit_k_max 44 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 2.41 _diffrn_reflns_theta_max 32.31 _reflns_number_total 3483 _reflns_number_gt 2001 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker, 2009)' _computing_cell_refinement 'SAINT (Bruker, 2009)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL (Sheldrick, 2008)' _computing_molecular_graphics 'X-Seed (Barbour 2001)' _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^)+(0.0619P)^2^+1.4116P] 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 3483 _refine_ls_number_parameters 131 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0966 _refine_ls_R_factor_gt 0.0506 _refine_ls_wR_factor_ref 0.1451 _refine_ls_wR_factor_gt 0.1192 _refine_ls_goodness_of_fit_ref 0.999 _refine_ls_restrained_S_all 0.999 _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 C1 C 0.07465(5) 0.22022(5) 0.4953(2) 0.0496(3) Uani 1 1 d . . . C2 C 0.02670(5) 0.17454(5) 0.5190(2) 0.0543(3) Uani 1 1 d . . . H2 H 0.0055 0.1701 0.6433 0.065 Uiso 1 1 calc R . . C3 C 0.01016(5) 0.13536(5) 0.3579(2) 0.0531(3) Uani 1 1 d . . . H3 H -0.0221 0.1044 0.3741 0.064 Uiso 1 1 calc R . . O4 O 0.02824(4) 0.10412(4) 0.00974(16) 0.0569(3) Uani 1 1 d . . . C4 C 0.04161(5) 0.14229(5) 0.1728(2) 0.0456(3) Uani 1 1 d . . . H4 H -0.0053(8) 0.0784(7) 0.020(3) 0.085(6) Uiso 1 1 d . . . C5 C 0.08930(5) 0.18859(5) 0.1479(2) 0.0527(3) Uani 1 1 d . . . H5 H 0.1101 0.1936 0.0216 0.063 Uiso 1 1 calc R . . C6 C 0.10601(5) 0.22734(5) 0.3106(2) 0.0561(3) Uani 1 1 d . . . H6 H 0.1384 0.2582 0.2955 0.067 Uiso 1 1 calc R . . O7 O 0.09219(4) 0.25675(4) 0.67044(16) 0.0620(3) Uani 1 1 d . . . C8 C 0.09299(4) 0.30399(5) 0.6422(2) 0.0453(3) Uani 1 1 d . . . C9 C 0.07559(5) 0.31745(5) 0.4514(2) 0.0514(3) Uani 1 1 d . . . H9 H 0.0633 0.2948 0.3281 0.062 Uiso 1 1 calc R . . C10 C 0.07678(6) 0.36550(6) 0.4471(3) 0.0645(4) Uani 1 1 d . . . H10 H 0.0647 0.3748 0.3199 0.077 Uiso 1 1 calc R . . C11 C 0.09546(6) 0.39957(6) 0.6274(3) 0.0679(4) Uani 1 1 d . . . H11 H 0.0962 0.4317 0.6220 0.082 Uiso 1 1 calc R . . C12 C 0.11298(6) 0.38554(6) 0.8154(3) 0.0630(4) Uani 1 1 d . . . H12 H 0.1258 0.4084 0.9376 0.076 Uiso 1 1 calc R . . C13 C 0.11166(5) 0.33778(5) 0.8242(2) 0.0525(3) Uani 1 1 d . . . H13 H 0.1233 0.3284 0.9524 0.063 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 C1 0.0534(7) 0.0456(6) 0.0531(7) 0.0016(5) -0.0072(5) 0.0273(6) C2 0.0505(7) 0.0572(8) 0.0555(7) 0.0037(6) 0.0060(6) 0.0272(6) C3 0.0377(6) 0.0488(7) 0.0657(8) 0.0042(6) 0.0059(5) 0.0162(5) O4 0.0468(5) 0.0541(5) 0.0670(6) -0.0100(4) -0.0015(4) 0.0231(4) C4 0.0397(6) 0.0453(6) 0.0547(7) 0.0009(5) -0.0023(5) 0.0235(5) C5 0.0427(6) 0.0511(7) 0.0601(7) 0.0047(6) 0.0080(5) 0.0204(5) C6 0.0434(6) 0.0444(7) 0.0698(8) 0.0058(6) 0.0006(6) 0.0139(5) O7 0.0827(7) 0.0522(5) 0.0569(6) -0.0047(4) -0.0197(5) 0.0380(5) C8 0.0389(6) 0.0464(6) 0.0510(6) 0.0051(5) 0.0019(5) 0.0217(5) C9 0.0468(6) 0.0573(7) 0.0514(7) 0.0052(6) -0.0004(5) 0.0271(6) C10 0.0681(9) 0.0736(10) 0.0669(9) 0.0204(7) 0.0101(7) 0.0466(8) C11 0.0749(10) 0.0593(8) 0.0808(10) 0.0107(8) 0.0203(8) 0.0419(8) C12 0.0646(9) 0.0598(8) 0.0680(9) -0.0054(7) 0.0084(7) 0.0336(7) C13 0.0488(7) 0.0587(7) 0.0511(7) -0.0020(6) 0.0001(5) 0.0277(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 C1 C6 1.3772(18) . ? C1 C2 1.3781(18) . ? C1 O7 1.3925(15) . ? C2 C3 1.3813(19) . ? C2 H2 0.9300 . ? C3 C4 1.3821(17) . ? C3 H3 0.9300 . ? O4 C4 1.3785(15) . ? O4 H4 0.891(19) . ? C4 C5 1.3833(17) . ? C5 C6 1.3793(19) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? O7 C8 1.3809(15) . ? C8 C9 1.3780(17) . ? C8 C13 1.3797(18) . ? C9 C10 1.3886(19) . ? C9 H9 0.9300 . ? C10 C11 1.376(2) . ? C10 H10 0.9300 . ? C11 C12 1.374(2) . ? C11 H11 0.9300 . ? C12 C13 1.379(2) . ? C12 H12 0.9300 . ? C13 H13 0.9300 . ? 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 C6 C1 C2 120.41(12) . . ? C6 C1 O7 121.11(12) . . ? C2 C1 O7 118.28(12) . . ? C1 C2 C3 119.89(12) . . ? C1 C2 H2 120.1 . . ? C3 C2 H2 120.1 . . ? C2 C3 C4 119.86(12) . . ? C2 C3 H3 120.1 . . ? C4 C3 H3 120.1 . . ? C4 O4 H4 112.4(11) . . ? O4 C4 C3 122.78(11) . . ? O4 C4 C5 117.21(11) . . ? C3 C4 C5 119.99(11) . . ? C6 C5 C4 119.99(12) . . ? C6 C5 H5 120.0 . . ? C4 C5 H5 120.0 . . ? C1 C6 C5 119.84(12) . . ? C1 C6 H6 120.1 . . ? C5 C6 H6 120.1 . . ? C8 O7 C1 119.54(10) . . ? C9 C8 C13 120.65(12) . . ? C9 C8 O7 124.20(11) . . ? C13 C8 O7 115.13(11) . . ? C8 C9 C10 118.58(13) . . ? C8 C9 H9 120.7 . . ? C10 C9 H9 120.7 . . ? C11 C10 C9 121.27(13) . . ? C11 C10 H10 119.4 . . ? C9 C10 H10 119.4 . . ? C12 C11 C10 119.19(14) . . ? C12 C11 H11 120.4 . . ? C10 C11 H11 120.4 . . ? C11 C12 C13 120.53(14) . . ? C11 C12 H12 119.7 . . ? C13 C12 H12 119.7 . . ? C12 C13 C8 119.77(13) . . ? C12 C13 H13 120.1 . . ? C8 C13 H13 120.1 . . ? 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 0.70(19) . . . . ? O7 C1 C2 C3 -174.31(11) . . . . ? C1 C2 C3 C4 -0.5(2) . . . . ? C2 C3 C4 O4 177.88(11) . . . . ? C2 C3 C4 C5 -0.64(19) . . . . ? O4 C4 C5 C6 -177.11(12) . . . . ? C3 C4 C5 C6 1.49(19) . . . . ? C2 C1 C6 C5 0.1(2) . . . . ? O7 C1 C6 C5 175.02(12) . . . . ? C4 C5 C6 C1 -1.2(2) . . . . ? C6 C1 O7 C8 76.07(16) . . . . ? C2 C1 O7 C8 -108.95(13) . . . . ? C1 O7 C8 C9 2.35(18) . . . . ? C1 O7 C8 C13 -179.18(11) . . . . ? C13 C8 C9 C10 -0.61(18) . . . . ? O7 C8 C9 C10 177.78(12) . . . . ? C8 C9 C10 C11 0.8(2) . . . . ? C9 C10 C11 C12 -0.3(2) . . . . ? C10 C11 C12 C13 -0.3(2) . . . . ? C11 C12 C13 C8 0.5(2) . . . . ? C9 C8 C13 C12 -0.03(18) . . . . ? O7 C8 C13 C12 -178.56(12) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O4 H4 O4 0.891(19) 1.850(19) 2.7311(10) 169.7(17) 12 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 32.31 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.145 _refine_diff_density_min -0.232 _refine_diff_density_rms 0.056 _database_code_depnum_ccdc_archive 'CCDC 959284'