# Electronic Supplementary Material (ESI) for CrystEngComm # 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_lithium _audit_creation_method SHELXL-97 _chemical_name_systematic ; lithium hemibenzoate ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H11 Li O4' _chemical_formula_weight 250.17 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' Li Li -0.0003 0.0001 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 5.3600(3) _cell_length_b 8.5693(7) _cell_length_c 13.4999(11) _cell_angle_alpha 98.830(4) _cell_angle_beta 93.800(5) _cell_angle_gamma 95.524(5) _cell_volume 607.80(8) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 16973 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.367 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 260 _exptl_absorpt_coefficient_mu 0.099 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6332 _exptl_absorpt_correction_T_max 0.7456 _exptl_absorpt_process_details 'SADABS 2007/2 (Sheldrick, G.M., 2007)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker-Nonius FR591 rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ; Bruker-Nonius Roper CCD camera on \k-goniostat ; _diffrn_measurement_method '\f & \w scans' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11772 _diffrn_reflns_av_R_equivalents 0.0698 _diffrn_reflns_av_sigmaI/netI 0.0689 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 3.59 _diffrn_reflns_theta_max 27.57 _reflns_number_total 2763 _reflns_number_gt 1833 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Hooft, R.W.W., 1998)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' #Although determined using DirAx, the cell is refined in the HKL #package during data reduction _computing_data_reduction 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0634P)^2^+0.0183P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.071(12) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2763 _refine_ls_number_parameters 177 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0948 _refine_ls_R_factor_gt 0.0538 _refine_ls_wR_factor_ref 0.1327 _refine_ls_wR_factor_gt 0.1173 _refine_ls_goodness_of_fit_ref 1.078 _refine_ls_restrained_S_all 1.078 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.3416(2) 0.16457(16) 0.49603(9) 0.0293(3) Uani 1 1 d . . . O2 O 0.6436(2) 0.22585(15) 0.39722(9) 0.0289(3) Uani 1 1 d . . . O3 O 0.5327(2) 0.56317(14) 0.38665(9) 0.0246(3) Uani 1 1 d . . . O4 O 0.1375(2) 0.48863(14) 0.41454(9) 0.0251(3) Uani 1 1 d . . . C1 C 0.3404(3) 0.0046(2) 0.33734(13) 0.0238(4) Uani 1 1 d . . . C2 C 0.4470(4) -0.0297(2) 0.24678(15) 0.0353(5) Uani 1 1 d . . . H2 H 0.5954 0.0318 0.2345 0.042 Uiso 1 1 calc R . . C3 C 0.3374(4) -0.1534(3) 0.17438(16) 0.0420(5) Uani 1 1 d . . . H3 H 0.4111 -0.1767 0.1125 0.050 Uiso 1 1 calc R . . C4 C 0.1213(4) -0.2434(2) 0.19147(15) 0.0324(5) Uani 1 1 d . . . H4 H 0.0463 -0.3280 0.1414 0.039 Uiso 1 1 calc R . . C5 C 0.0155(4) -0.2099(2) 0.28106(15) 0.0336(5) Uani 1 1 d . . . H5 H -0.1327 -0.2720 0.2930 0.040 Uiso 1 1 calc R . . C6 C 0.1233(3) -0.0863(2) 0.35409(15) 0.0304(5) Uani 1 1 d . . . H6 H 0.0486 -0.0635 0.4158 0.037 Uiso 1 1 calc R . . C7 C 0.4566(3) 0.1406(2) 0.41272(13) 0.0238(4) Uani 1 1 d . . . C11 C 0.2738(3) 0.4015(2) 0.25246(13) 0.0233(4) Uani 1 1 d . . . C12 C 0.4525(3) 0.4232(2) 0.18472(14) 0.0289(4) Uani 1 1 d . . . H12 H 0.6004 0.4942 0.2055 0.035 Uiso 1 1 calc R . . C13 C 0.4170(4) 0.3421(2) 0.08652(15) 0.0344(5) Uani 1 1 d . . . H13 H 0.5383 0.3594 0.0401 0.041 Uiso 1 1 calc R . . C14 C 0.2045(4) 0.2362(2) 0.05679(15) 0.0347(5) Uani 1 1 d . . . H14 H 0.1803 0.1799 -0.0101 0.042 Uiso 1 1 calc R . . C15 C 0.0269(4) 0.2121(3) 0.12436(15) 0.0367(5) Uani 1 1 d . . . H15 H -0.1184 0.1386 0.1039 0.044 Uiso 1 1 calc R . . C16 C 0.0605(3) 0.2947(2) 0.22178(14) 0.0303(5) Uani 1 1 d . . . H16 H -0.0626 0.2784 0.2677 0.036 Uiso 1 1 calc R . . C17 C 0.3151(3) 0.4908(2) 0.35824(13) 0.0214(4) Uani 1 1 d . . . Li1 Li 0.7918(5) 0.4407(4) 0.4387(2) 0.0280(7) Uani 1 1 d . . . H1 H 0.408(5) 0.271(4) 0.541(2) 0.091(10) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0290(7) 0.0275(7) 0.0292(7) 0.0003(6) 0.0075(6) -0.0046(6) O2 0.0257(7) 0.0266(7) 0.0321(8) 0.0016(6) 0.0044(5) -0.0051(6) O3 0.0192(6) 0.0250(7) 0.0272(7) 0.0000(5) 0.0031(5) -0.0037(5) O4 0.0209(6) 0.0279(7) 0.0254(7) 0.0024(5) 0.0046(5) -0.0016(5) C1 0.0241(9) 0.0197(9) 0.0271(10) 0.0045(7) 0.0013(7) 0.0001(7) C2 0.0358(11) 0.0325(11) 0.0345(11) -0.0009(9) 0.0111(9) -0.0073(9) C3 0.0494(13) 0.0388(12) 0.0328(12) -0.0066(9) 0.0103(9) -0.0051(10) C4 0.0363(11) 0.0245(10) 0.0328(11) -0.0006(8) -0.0044(9) -0.0022(8) C5 0.0320(10) 0.0283(11) 0.0371(12) 0.0033(9) -0.0018(9) -0.0080(8) C6 0.0299(10) 0.0292(10) 0.0299(10) 0.0016(8) 0.0038(8) -0.0045(8) C7 0.0229(9) 0.0218(9) 0.0268(10) 0.0052(7) 0.0027(7) 0.0002(7) C11 0.0196(9) 0.0241(10) 0.0263(10) 0.0040(8) 0.0009(7) 0.0037(7) C12 0.0265(10) 0.0284(10) 0.0294(10) 0.0006(8) 0.0036(8) -0.0025(8) C13 0.0363(11) 0.0365(12) 0.0302(11) 0.0029(9) 0.0093(9) 0.0015(9) C14 0.0375(11) 0.0377(12) 0.0259(10) -0.0033(8) -0.0003(8) 0.0040(9) C15 0.0270(10) 0.0402(12) 0.0363(12) -0.0088(9) -0.0019(8) -0.0031(9) C16 0.0232(9) 0.0345(11) 0.0305(11) -0.0002(8) 0.0032(8) -0.0033(8) C17 0.0193(9) 0.0178(9) 0.0272(10) 0.0044(7) 0.0028(7) 0.0010(7) Li1 0.0219(15) 0.0317(17) 0.0288(16) 0.0031(13) 0.0032(12) -0.0032(13) _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 1.316(2) . ? O1 H1 1.03(3) . ? O2 C7 1.231(2) . ? O2 Li1 1.917(3) . ? O3 C17 1.273(2) . ? O3 Li1 1.975(3) . ? O4 C17 1.257(2) . ? O4 Li1 1.919(3) 1_455 ? O4 Li1 1.981(3) 2_666 ? C1 C2 1.386(3) . ? C1 C6 1.387(3) . ? C1 C7 1.481(2) . ? C2 C3 1.382(3) . ? C2 H2 0.9500 . ? C3 C4 1.381(3) . ? C3 H3 0.9500 . ? C4 C5 1.372(3) . ? C4 H4 0.9500 . ? C5 C6 1.384(3) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C11 C12 1.387(3) . ? C11 C16 1.391(2) . ? C11 C17 1.505(2) . ? C12 C13 1.391(3) . ? C12 H12 0.9500 . ? C13 C14 1.382(3) . ? C13 H13 0.9500 . ? C14 C15 1.384(3) . ? C14 H14 0.9500 . ? C15 C16 1.386(3) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? Li1 O4 1.919(3) 1_655 ? Li1 O4 1.981(3) 2_666 ? Li1 Li1 2.704(6) 2_766 ? 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 112.7(16) . . ? C7 O2 Li1 138.24(14) . . ? C17 O3 Li1 117.96(14) . . ? C17 O4 Li1 152.51(15) . 1_455 ? C17 O4 Li1 119.63(13) . 2_666 ? Li1 O4 Li1 87.78(13) 1_455 2_666 ? C2 C1 C6 119.31(17) . . ? C2 C1 C7 119.15(16) . . ? C6 C1 C7 121.52(16) . . ? C3 C2 C1 120.02(18) . . ? C3 C2 H2 120.0 . . ? C1 C2 H2 120.0 . . ? C4 C3 C2 120.42(19) . . ? C4 C3 H3 119.8 . . ? C2 C3 H3 119.8 . . ? C5 C4 C3 119.73(18) . . ? C5 C4 H4 120.1 . . ? C3 C4 H4 120.1 . . ? C4 C5 C6 120.39(18) . . ? C4 C5 H5 119.8 . . ? C6 C5 H5 119.8 . . ? C5 C6 C1 120.14(18) . . ? C5 C6 H6 119.9 . . ? C1 C6 H6 119.9 . . ? O2 C7 O1 122.98(16) . . ? O2 C7 C1 122.18(16) . . ? O1 C7 C1 114.83(15) . . ? C12 C11 C16 119.22(17) . . ? C12 C11 C17 119.78(16) . . ? C16 C11 C17 120.99(16) . . ? C11 C12 C13 120.56(18) . . ? C11 C12 H12 119.7 . . ? C13 C12 H12 119.7 . . ? C14 C13 C12 119.76(18) . . ? C14 C13 H13 120.1 . . ? C12 C13 H13 120.1 . . ? C13 C14 C15 120.03(18) . . ? C13 C14 H14 120.0 . . ? C15 C14 H14 120.0 . . ? C14 C15 C16 120.21(18) . . ? C14 C15 H15 119.9 . . ? C16 C15 H15 119.9 . . ? C15 C16 C11 120.20(18) . . ? C15 C16 H16 119.9 . . ? C11 C16 H16 119.9 . . ? O4 C17 O3 123.22(16) . . ? O4 C17 C11 119.26(15) . . ? O3 C17 C11 117.51(15) . . ? O2 Li1 O4 117.38(16) . 1_655 ? O2 Li1 O3 102.18(14) . . ? O4 Li1 O3 119.95(17) 1_655 . ? O2 Li1 O4 116.27(16) . 2_666 ? O4 Li1 O4 92.22(13) 1_655 2_666 ? O3 Li1 O4 109.28(15) . 2_666 ? O2 Li1 Li1 130.6(2) . 2_766 ? O4 Li1 Li1 47.06(10) 1_655 2_766 ? O3 Li1 Li1 126.6(2) . 2_766 ? O4 Li1 Li1 45.16(10) 2_666 2_766 ? _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.232 _refine_diff_density_min -0.271 _refine_diff_density_rms 0.059 _vrf_PLAT430_lithium ; PROBLEM: Short Inter D...A Contact O4 .. O4 .. 2.81 Ang. RESPONSE: These two atoms are part of a centrosymmetric Li2O2 square. ; _vrf_PLAT355_lithium ; PROBLEM: Long O-H Bond (0.82A) O1 - H1 ... 1.03 Ang. RESPONSE: The position of this H atom was allowed to refine, sinc H bonding was a theme to this work. ; _database_code_depnum_ccdc_archive 'CCDC 940110' ####################################################################### # # 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_sodium4a _audit_creation_method SHELXL-97 _chemical_name_systematic ; Sodium benzoate.2benzoic acid ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H17 Na O6' _chemical_formula_weight 388.34 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' Na Na 0.0362 0.0249 '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 5.80770(10) _cell_length_b 14.4331(4) _cell_length_c 22.0139(6) _cell_angle_alpha 90.00 _cell_angle_beta 97.047(2) _cell_angle_gamma 90.00 _cell_volume 1831.33(8) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 9263 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description blade _exptl_crystal_colour colourless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.408 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 808 _exptl_absorpt_coefficient_mu 0.123 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.652 _exptl_absorpt_correction_T_max 0.746 _exptl_absorpt_process_details 'SADABS 2007/2 (Sheldrick, G.M., 2007)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker-Nonius FR591 rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ; Bruker-Nonius Roper CCD camera on \k-goniostat ; _diffrn_measurement_method '\f & \w scans' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 21737 _diffrn_reflns_av_R_equivalents 0.0409 _diffrn_reflns_av_sigmaI/netI 0.0339 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 2.97 _diffrn_reflns_theta_max 27.51 _reflns_number_total 4185 _reflns_number_gt 3434 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Hooft, R.W.W., 1998)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' #Although determined using DirAx, the cell is refined in the HKL #package during data reduction _computing_data_reduction 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0483P)^2^+0.6575P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens mixed _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4185 _refine_ls_number_parameters 261 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0526 _refine_ls_R_factor_gt 0.0405 _refine_ls_wR_factor_ref 0.1023 _refine_ls_wR_factor_gt 0.0957 _refine_ls_goodness_of_fit_ref 1.043 _refine_ls_restrained_S_all 1.043 _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 Na1 Na 0.41188(9) 0.38482(4) 0.98674(2) 0.01707(14) Uani 1 1 d . . . O1A O 0.02415(16) 0.38149(6) 1.04046(4) 0.0163(2) Uani 1 1 d . . . O2A O -0.28857(15) 0.46829(6) 1.04742(4) 0.0156(2) Uani 1 1 d . . . C1A C -0.0012(2) 0.46076(9) 1.13424(6) 0.0125(3) Uani 1 1 d . . . C2A C 0.2264(2) 0.43890(9) 1.15800(6) 0.0151(3) Uani 1 1 d . . . H2A H 0.3268 0.4103 1.1326 0.018 Uiso 1 1 calc R . . C3A C 0.3062(2) 0.45897(10) 1.21872(7) 0.0184(3) Uani 1 1 d . . . H3A H 0.4612 0.4440 1.2347 0.022 Uiso 1 1 calc R . . C4A C 0.1607(2) 0.50078(10) 1.25606(6) 0.0192(3) Uani 1 1 d . . . H4A H 0.2156 0.5142 1.2976 0.023 Uiso 1 1 calc R . . C5A C -0.0659(2) 0.52291(10) 1.23257(7) 0.0192(3) Uani 1 1 d . . . H5A H -0.1658 0.5517 1.2580 0.023 Uiso 1 1 calc R . . C6A C -0.1462(2) 0.50305(9) 1.17206(6) 0.0156(3) Uani 1 1 d . . . H6A H -0.3011 0.5183 1.1562 0.019 Uiso 1 1 calc R . . C7A C -0.0969(2) 0.43644(9) 1.06976(6) 0.0124(3) Uani 1 1 d . . . O1B O 0.79092(16) 0.34214(7) 0.93723(5) 0.0193(2) Uani 1 1 d . . . O2B O 0.14684(15) 0.30221(7) 0.91828(4) 0.0181(2) Uani 1 1 d . . . C1B C 0.8359(2) 0.28536(9) 0.83810(6) 0.0135(3) Uani 1 1 d . . . C2B C 0.6065(2) 0.30552(9) 0.81559(6) 0.0163(3) Uani 1 1 d . . . H2B H 0.5059 0.3323 0.8417 0.020 Uiso 1 1 calc R . . C3B C 0.5256(2) 0.28635(10) 0.75489(7) 0.0199(3) Uani 1 1 d . . . H3B H 0.3698 0.3007 0.7394 0.024 Uiso 1 1 calc R . . C4B C 0.6710(2) 0.24645(10) 0.71675(7) 0.0199(3) Uani 1 1 d . . . H4B H 0.6150 0.2340 0.6752 0.024 Uiso 1 1 calc R . . C5B C 0.8983(2) 0.22463(10) 0.73929(7) 0.0199(3) Uani 1 1 d . . . H5B H 0.9973 0.1964 0.7134 0.024 Uiso 1 1 calc R . . C6B C 0.9804(2) 0.24406(10) 0.79972(7) 0.0171(3) Uani 1 1 d . . . H6B H 1.1360 0.2292 0.8151 0.020 Uiso 1 1 calc R . . C7B C 0.9385(2) 0.31004(9) 0.90129(6) 0.0140(3) Uani 1 1 d . . . O1C O 0.16706(18) 0.21606(8) 1.08356(5) 0.0257(3) Uani 1 1 d . . . O2C O 0.49749(17) 0.25314(7) 1.04668(5) 0.0220(2) Uani 1 1 d . . . C1C C 0.4473(2) 0.09834(9) 1.08128(6) 0.0163(3) Uani 1 1 d . . . C2C C 0.3055(2) 0.03742(10) 1.10859(7) 0.0210(3) Uani 1 1 d . . . H2C H 0.1668 0.0593 1.1225 0.025 Uiso 1 1 calc R . . C3C C 0.3664(3) -0.05551(10) 1.11557(7) 0.0260(3) Uani 1 1 d . . . H3C H 0.2702 -0.0970 1.1346 0.031 Uiso 1 1 calc R . . C4C C 0.5677(3) -0.08761(11) 1.09469(7) 0.0262(3) Uani 1 1 d . . . H4C H 0.6069 -0.1514 1.0982 0.031 Uiso 1 1 calc R . . C5C C 0.7117(2) -0.02657(11) 1.06869(7) 0.0234(3) Uani 1 1 d . . . H5C H 0.8510 -0.0486 1.0553 0.028 Uiso 1 1 calc R . . C6C C 0.6540(2) 0.06672(10) 1.06208(7) 0.0199(3) Uani 1 1 d . . . H6C H 0.7540 0.1085 1.0447 0.024 Uiso 1 1 calc R . . C7C C 0.3764(2) 0.19648(9) 1.06885(6) 0.0165(3) Uani 1 1 d . . . H1B H 0.878(4) 0.3548(16) 0.9740(11) 0.061(7) Uiso 1 1 d . . . H1C H 0.129(4) 0.2719(17) 1.0719(11) 0.057(7) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Na1 0.0171(3) 0.0133(3) 0.0193(3) 0.0019(2) -0.0043(2) -0.0011(2) O1A 0.0172(5) 0.0180(5) 0.0135(5) -0.0025(4) 0.0009(4) 0.0042(4) O2A 0.0141(5) 0.0142(5) 0.0174(5) 0.0010(4) -0.0027(4) 0.0012(3) C1A 0.0146(6) 0.0105(6) 0.0124(6) 0.0019(5) 0.0014(5) -0.0012(5) C2A 0.0139(6) 0.0156(7) 0.0161(7) 0.0015(5) 0.0028(5) 0.0001(5) C3A 0.0147(6) 0.0212(7) 0.0181(7) 0.0027(6) -0.0023(5) -0.0017(5) C4A 0.0244(7) 0.0197(7) 0.0129(7) -0.0005(5) -0.0004(5) -0.0053(6) C5A 0.0236(7) 0.0184(7) 0.0165(7) -0.0012(6) 0.0065(6) 0.0012(5) C6A 0.0146(6) 0.0150(6) 0.0173(7) 0.0011(5) 0.0021(5) 0.0007(5) C7A 0.0131(6) 0.0102(6) 0.0139(6) 0.0028(5) 0.0012(5) -0.0018(5) O1B 0.0149(5) 0.0288(6) 0.0140(5) -0.0048(4) 0.0011(4) 0.0021(4) O2B 0.0143(5) 0.0209(5) 0.0182(5) -0.0037(4) -0.0013(4) 0.0012(4) C1B 0.0151(6) 0.0115(6) 0.0141(7) 0.0001(5) 0.0022(5) -0.0016(5) C2B 0.0157(6) 0.0168(7) 0.0164(7) -0.0008(5) 0.0027(5) 0.0011(5) C3B 0.0152(7) 0.0215(7) 0.0220(8) 0.0009(6) -0.0019(5) 0.0012(5) C4B 0.0234(7) 0.0204(7) 0.0148(7) -0.0036(6) -0.0017(5) -0.0020(6) C5B 0.0216(7) 0.0193(7) 0.0189(7) -0.0050(6) 0.0033(6) 0.0025(5) C6B 0.0142(6) 0.0174(7) 0.0191(7) -0.0020(5) 0.0001(5) 0.0008(5) C7B 0.0158(6) 0.0116(6) 0.0148(7) 0.0009(5) 0.0024(5) -0.0008(5) O1C 0.0227(6) 0.0171(6) 0.0389(7) 0.0070(5) 0.0105(5) 0.0051(4) O2C 0.0202(5) 0.0181(5) 0.0272(6) 0.0076(4) 0.0010(4) -0.0008(4) C1C 0.0182(7) 0.0145(7) 0.0151(7) 0.0004(5) -0.0031(5) -0.0001(5) C2C 0.0215(7) 0.0195(7) 0.0216(8) 0.0032(6) 0.0007(6) -0.0007(5) C3C 0.0295(8) 0.0190(7) 0.0278(8) 0.0057(6) -0.0030(6) -0.0049(6) C4C 0.0330(8) 0.0160(7) 0.0259(8) -0.0010(6) -0.0114(6) 0.0042(6) C5C 0.0216(7) 0.0236(8) 0.0228(8) -0.0040(6) -0.0057(6) 0.0068(6) C6C 0.0184(7) 0.0222(7) 0.0182(7) 0.0003(6) -0.0019(5) -0.0001(5) C7C 0.0170(7) 0.0169(7) 0.0148(7) 0.0004(5) -0.0018(5) 0.0004(5) _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 Na1 O2C 2.3322(11) . ? Na1 O2A 2.3326(10) 3_567 ? Na1 O2B 2.3436(11) . ? Na1 O2A 2.3859(10) 1_655 ? Na1 O1B 2.6461(11) . ? Na1 O1A 2.6693(10) . ? Na1 Na1 3.5067(10) 3_667 ? O1A C7A 1.2847(15) . ? O2A C7A 1.2482(15) . ? O2A Na1 2.3326(10) 3_567 ? O2A Na1 2.3859(10) 1_455 ? C1A C6A 1.3953(18) . ? C1A C2A 1.3966(18) . ? C1A C7A 1.5012(18) . ? C2A C3A 1.3905(19) . ? C2A H2A 0.9500 . ? C3A C4A 1.387(2) . ? C3A H3A 0.9500 . ? C4A C5A 1.391(2) . ? C4A H4A 0.9500 . ? C5A C6A 1.386(2) . ? C5A H5A 0.9500 . ? C6A H6A 0.9500 . ? O1B C7B 1.3194(16) . ? O1B H1B 0.92(2) . ? O2B C7B 1.2273(16) 1_455 ? C1B C2B 1.3938(18) . ? C1B C6B 1.3956(18) . ? C1B C7B 1.4878(18) . ? C2B C3B 1.389(2) . ? C2B H2B 0.9500 . ? C3B C4B 1.387(2) . ? C3B H3B 0.9500 . ? C4B C5B 1.388(2) . ? C4B H4B 0.9500 . ? C5B C6B 1.386(2) . ? C5B H5B 0.9500 . ? C6B H6B 0.9500 . ? C7B O2B 1.2273(16) 1_655 ? O1C C7C 1.3262(17) . ? O1C H1C 0.87(2) . ? O2C C7C 1.2192(17) . ? C1C C2C 1.391(2) . ? C1C C6C 1.397(2) . ? C1C C7C 1.4910(19) . ? C2C C3C 1.391(2) . ? C2C H2C 0.9500 . ? C3C C4C 1.388(2) . ? C3C H3C 0.9500 . ? C4C C5C 1.385(2) . ? C4C H4C 0.9500 . ? C5C C6C 1.391(2) . ? C5C H5C 0.9500 . ? C6C H6C 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 O2C Na1 O2A 163.49(4) . 3_567 ? O2C Na1 O2B 91.54(4) . . ? O2A Na1 O2B 95.95(4) 3_567 . ? O2C Na1 O2A 90.26(4) . 1_655 ? O2A Na1 O2A 84.00(4) 3_567 1_655 ? O2B Na1 O2A 173.31(4) . 1_655 ? O2C Na1 O1B 85.01(4) . . ? O2A Na1 O1B 108.47(4) 3_567 . ? O2B Na1 O1B 97.51(4) . . ? O2A Na1 O1B 76.22(3) 1_655 . ? O2C Na1 O1A 82.39(4) . . ? O2A Na1 O1A 85.23(3) 3_567 . ? O2B Na1 O1A 75.67(3) . . ? O2A Na1 O1A 110.97(4) 1_655 . ? O1B Na1 O1A 165.46(4) . . ? O2C Na1 Na1 129.85(4) . 3_667 ? O2A Na1 Na1 42.58(2) 3_567 3_667 ? O2B Na1 Na1 138.13(4) . 3_667 ? O2A Na1 Na1 41.42(2) 1_655 3_667 ? O1B Na1 Na1 92.79(3) . 3_667 ? O1A Na1 Na1 100.84(3) . 3_667 ? C7A O1A Na1 139.00(8) . . ? C7A O2A Na1 133.27(8) . 3_567 ? C7A O2A Na1 126.04(8) . 1_455 ? Na1 O2A Na1 96.00(4) 3_567 1_455 ? C6A C1A C2A 119.22(12) . . ? C6A C1A C7A 119.06(11) . . ? C2A C1A C7A 121.67(12) . . ? C3A C2A C1A 120.11(12) . . ? C3A C2A H2A 119.9 . . ? C1A C2A H2A 119.9 . . ? C4A C3A C2A 120.30(12) . . ? C4A C3A H3A 119.8 . . ? C2A C3A H3A 119.9 . . ? C3A C4A C5A 119.82(13) . . ? C3A C4A H4A 120.1 . . ? C5A C4A H4A 120.1 . . ? C6A C5A C4A 120.08(13) . . ? C6A C5A H5A 120.0 . . ? C4A C5A H5A 120.0 . . ? C5A C6A C1A 120.48(12) . . ? C5A C6A H6A 119.8 . . ? C1A C6A H6A 119.8 . . ? O2A C7A O1A 123.10(12) . . ? O2A C7A C1A 119.69(11) . . ? O1A C7A C1A 117.20(11) . . ? C7B O1B Na1 164.35(9) . . ? C7B O1B H1B 105.7(13) . . ? Na1 O1B H1B 89.3(13) . . ? C7B O2B Na1 133.98(9) 1_455 . ? C2B C1B C6B 119.56(12) . . ? C2B C1B C7B 122.55(12) . . ? C6B C1B C7B 117.82(11) . . ? C3B C2B C1B 119.76(12) . . ? C3B C2B H2B 120.1 . . ? C1B C2B H2B 120.1 . . ? C4B C3B C2B 120.39(13) . . ? C4B C3B H3B 119.8 . . ? C2B C3B H3B 119.8 . . ? C3B C4B C5B 120.05(13) . . ? C3B C4B H4B 120.0 . . ? C5B C4B H4B 120.0 . . ? C6B C5B C4B 119.81(13) . . ? C6B C5B H5B 120.1 . . ? C4B C5B H5B 120.1 . . ? C5B C6B C1B 120.40(12) . . ? C5B C6B H6B 119.8 . . ? C1B C6B H6B 119.8 . . ? O2B C7B O1B 122.56(12) 1_655 . ? O2B C7B C1B 121.98(12) 1_655 . ? O1B C7B C1B 115.45(11) . . ? C7C O1C H1C 109.4(15) . . ? C7C O2C Na1 132.82(9) . . ? C2C C1C C6C 120.03(13) . . ? C2C C1C C7C 121.00(12) . . ? C6C C1C C7C 118.89(13) . . ? C1C C2C C3C 120.09(14) . . ? C1C C2C H2C 120.0 . . ? C3C C2C H2C 120.0 . . ? C4C C3C C2C 119.91(14) . . ? C4C C3C H3C 120.0 . . ? C2C C3C H3C 120.0 . . ? C5C C4C C3C 120.02(14) . . ? C5C C4C H4C 120.0 . . ? C3C C4C H4C 120.0 . . ? C4C C5C C6C 120.60(14) . . ? C4C C5C H5C 119.7 . . ? C6C C5C H5C 119.7 . . ? C5C C6C C1C 119.30(14) . . ? C5C C6C H6C 120.3 . . ? C1C C6C H6C 120.3 . . ? O2C C7C O1C 123.10(13) . . ? O2C C7C C1C 123.42(12) . . ? O1C C7C C1C 113.48(12) . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.267 _refine_diff_density_min -0.287 _refine_diff_density_rms 0.058 _vrf_PLAT774_sodium4a ; PROBLEM: Note: Suspect X-Y Bond in CIF: NA1 -- NA1 .. 3.51 Ang. RESPONSE: These atoms are involved in a Na2O2 square. ; _database_code_depnum_ccdc_archive 'CCDC 940111' ####################################################################### # # 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_k_edens _audit_creation_method SHELXL-97 _chemical_name_systematic ; potassium hemibenzoate ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H11 K O4' _chemical_formula_weight 282.33 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' K K 0.2009 0.2494 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 29.586(2) _cell_length_b 3.7964(3) _cell_length_c 11.1214(8) _cell_angle_alpha 90.00 _cell_angle_beta 97.096(9) _cell_angle_gamma 90.00 _cell_volume 1239.59(16) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 27697 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.513 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 584 _exptl_absorpt_coefficient_mu 0.435 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.534 _exptl_absorpt_correction_T_max 0.746 _exptl_absorpt_process_details 'SADABS 2007/2 (Sheldrick, G.M., 2007)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker-Nonius FR591 rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ; Bruker-Nonius Roper CCD camera on \k-goniostat ; _diffrn_measurement_method '\f & \w scans' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12549 _diffrn_reflns_av_R_equivalents 0.0729 _diffrn_reflns_av_sigmaI/netI 0.0406 _diffrn_reflns_limit_h_min -38 _diffrn_reflns_limit_h_max 38 _diffrn_reflns_limit_k_min -4 _diffrn_reflns_limit_k_max 4 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 3.69 _diffrn_reflns_theta_max 27.65 _reflns_number_total 1428 _reflns_number_gt 1203 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Hooft, R.W.W., 1998)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' #Although determined using DirAx, the cell is refined in the HKL #package during data reduction _computing_data_reduction 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0569P)^2^+1.7439P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1428 _refine_ls_number_parameters 91 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0545 _refine_ls_R_factor_gt 0.0432 _refine_ls_wR_factor_ref 0.1114 _refine_ls_wR_factor_gt 0.1054 _refine_ls_goodness_of_fit_ref 1.051 _refine_ls_restrained_S_all 1.051 _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 K1 K 0.5000 0.17895(15) 0.2500 0.0211(2) Uani 1 2 d S . . O1 O 0.53807(5) 0.4532(4) 0.05538(12) 0.0233(3) Uani 1 1 d . . . O2 O 0.55495(4) 0.2979(4) -0.12732(12) 0.0206(3) Uani 1 1 d . . . C1 C 0.61423(6) 0.2898(5) 0.03879(16) 0.0172(4) Uani 1 1 d . . . C2 C 0.62849(6) 0.3894(5) 0.15862(17) 0.0185(4) Uani 1 1 d . . . H2 H 0.6074 0.4884 0.2068 0.022 Uiso 1 1 calc R . . C3 C 0.67371(6) 0.3426(5) 0.20676(17) 0.0195(4) Uani 1 1 d . . . H3 H 0.6835 0.4128 0.2878 0.023 Uiso 1 1 calc R . . C4 C 0.70464(6) 0.1942(5) 0.13737(17) 0.0202(4) Uani 1 1 d . . . H4 H 0.7355 0.1630 0.1709 0.024 Uiso 1 1 calc R . . C5 C 0.69043(6) 0.0907(5) 0.01825(18) 0.0208(4) Uani 1 1 d . . . H5 H 0.7115 -0.0126 -0.0292 0.025 Uiso 1 1 calc R . . C6 C 0.64541(6) 0.1392(5) -0.03053(17) 0.0191(4) Uani 1 1 d . . . H6 H 0.6357 0.0694 -0.1117 0.023 Uiso 1 1 calc R . . C7 C 0.56618(6) 0.3463(5) -0.01706(17) 0.0181(4) Uani 1 1 d . . . H1 H 0.5114(12) 0.473(11) 0.020(3) 0.005(10) Uiso 0.50 1 d P . . 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 K1 0.0268(3) 0.0156(3) 0.0202(3) 0.000 -0.0006(2) 0.000 O1 0.0190(7) 0.0299(8) 0.0204(7) -0.0001(6) 0.0006(6) 0.0033(6) O2 0.0233(7) 0.0192(7) 0.0186(7) -0.0010(5) 0.0001(5) 0.0007(5) C1 0.0208(9) 0.0106(8) 0.0204(9) 0.0026(7) 0.0029(7) -0.0010(7) C2 0.0217(9) 0.0143(9) 0.0196(9) 0.0019(7) 0.0030(7) -0.0003(7) C3 0.0245(10) 0.0145(9) 0.0193(9) 0.0013(7) 0.0013(7) -0.0027(7) C4 0.0197(9) 0.0151(9) 0.0250(10) 0.0034(7) -0.0001(7) -0.0001(7) C5 0.0236(10) 0.0134(9) 0.0261(10) 0.0008(7) 0.0061(8) 0.0012(7) C6 0.0250(10) 0.0139(9) 0.0185(9) 0.0000(7) 0.0034(7) 0.0003(7) C7 0.0229(9) 0.0116(9) 0.0197(9) 0.0023(7) 0.0030(7) -0.0006(7) _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 K1 O2 2.6895(14) 5_655 ? K1 O2 2.6895(14) 6_556 ? K1 O1 2.7641(14) 2_655 ? K1 O1 2.7641(14) . ? K1 O2 2.8110(14) 6_566 ? K1 O2 2.8110(14) 5_665 ? K1 K1 3.7964(3) 1_545 ? K1 K1 3.7964(3) 1_565 ? K1 H1 2.85(4) . ? O1 C7 1.293(2) . ? O1 H1 0.84(3) . ? O2 C7 1.244(2) . ? O2 K1 2.6895(14) 5_655 ? O2 K1 2.8110(14) 5_665 ? C1 C6 1.396(3) . ? C1 C2 1.399(3) . ? C1 C7 1.495(3) . ? C2 C3 1.390(3) . ? C2 H2 0.9500 . ? C3 C4 1.387(3) . ? C3 H3 0.9500 . ? C4 C5 1.396(3) . ? C4 H4 0.9500 . ? C5 C6 1.387(3) . ? C5 H5 0.9500 . ? C6 H6 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 O2 K1 O2 95.39(6) 5_655 6_556 ? O2 K1 O1 111.81(4) 5_655 2_655 ? O2 K1 O1 97.79(4) 6_556 2_655 ? O2 K1 O1 97.79(4) 5_655 . ? O2 K1 O1 111.81(4) 6_556 . ? O1 K1 O1 135.74(6) 2_655 . ? O2 K1 O2 177.35(4) 5_655 6_566 ? O2 K1 O2 87.26(4) 6_556 6_566 ? O1 K1 O2 67.73(4) 2_655 6_566 ? O1 K1 O2 81.18(4) . 6_566 ? O2 K1 O2 87.26(4) 5_655 5_665 ? O2 K1 O2 177.35(4) 6_556 5_665 ? O1 K1 O2 81.18(4) 2_655 5_665 ? O1 K1 O2 67.73(4) . 5_665 ? O2 K1 O2 90.09(6) 6_566 5_665 ? O2 K1 K1 47.70(3) 5_655 1_545 ? O2 K1 K1 47.70(3) 6_556 1_545 ? O1 K1 K1 112.13(3) 2_655 1_545 ? O1 K1 K1 112.13(3) . 1_545 ? O2 K1 K1 134.96(3) 6_566 1_545 ? O2 K1 K1 134.96(3) 5_665 1_545 ? O2 K1 K1 132.30(3) 5_655 1_565 ? O2 K1 K1 132.30(3) 6_556 1_565 ? O1 K1 K1 67.87(3) 2_655 1_565 ? O1 K1 K1 67.87(3) . 1_565 ? O2 K1 K1 45.04(3) 6_566 1_565 ? O2 K1 K1 45.04(3) 5_665 1_565 ? K1 K1 K1 180.0 1_545 1_565 ? O2 K1 H1 86.5(8) 5_655 . ? O2 K1 H1 126.0(7) 6_556 . ? O1 K1 H1 131.3(8) 2_655 . ? O1 K1 H1 17.1(7) . . ? O2 K1 H1 91.9(8) 6_566 . ? O2 K1 H1 54.0(8) 5_665 . ? K1 K1 H1 113.1(9) 1_545 . ? K1 K1 H1 66.9(9) 1_565 . ? C7 O1 K1 136.52(12) . . ? C7 O1 H1 112(3) . . ? K1 O1 H1 87(3) . . ? C7 O2 K1 132.12(12) . 5_655 ? C7 O2 K1 116.23(11) . 5_665 ? K1 O2 K1 87.26(4) 5_655 5_665 ? C6 C1 C2 119.64(17) . . ? C6 C1 C7 119.26(17) . . ? C2 C1 C7 121.09(17) . . ? C3 C2 C1 119.68(17) . . ? C3 C2 H2 120.2 . . ? C1 C2 H2 120.2 . . ? C4 C3 C2 120.48(17) . . ? C4 C3 H3 119.8 . . ? C2 C3 H3 119.8 . . ? C3 C4 C5 120.01(17) . . ? C3 C4 H4 120.0 . . ? C5 C4 H4 120.0 . . ? C6 C5 C4 119.74(17) . . ? C6 C5 H5 120.1 . . ? C4 C5 H5 120.1 . . ? C5 C6 C1 120.44(17) . . ? C5 C6 H6 119.8 . . ? C1 C6 H6 119.8 . . ? O2 C7 O1 123.15(17) . . ? O2 C7 C1 120.85(17) . . ? O1 C7 C1 115.98(16) . . ? 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 O2 K1 O1 C7 -70.22(17) 5_655 . . . ? O2 K1 O1 C7 28.81(18) 6_556 . . . ? O1 K1 O1 C7 157.12(17) 2_655 . . . ? O2 K1 O1 C7 112.25(17) 6_566 . . . ? O2 K1 O1 C7 -154.01(18) 5_665 . . . ? K1 K1 O1 C7 -22.88(17) 1_545 . . . ? K1 K1 O1 C7 157.12(17) 1_565 . . . ? C6 C1 C2 C3 1.1(3) . . . . ? C7 C1 C2 C3 -178.15(16) . . . . ? C1 C2 C3 C4 -0.8(3) . . . . ? C2 C3 C4 C5 0.0(3) . . . . ? C3 C4 C5 C6 0.5(3) . . . . ? C4 C5 C6 C1 -0.2(3) . . . . ? C2 C1 C6 C5 -0.6(3) . . . . ? C7 C1 C6 C5 178.64(16) . . . . ? K1 O2 C7 O1 -67.8(2) 5_655 . . . ? K1 O2 C7 O1 44.1(2) 5_665 . . . ? K1 O2 C7 C1 113.57(17) 5_655 . . . ? K1 O2 C7 C1 -134.49(14) 5_665 . . . ? K1 O1 C7 O2 114.02(18) . . . . ? K1 O1 C7 C1 -67.3(2) . . . . ? C6 C1 C7 O2 -8.1(3) . . . . ? C2 C1 C7 O2 171.14(17) . . . . ? C6 C1 C7 O1 173.23(16) . . . . ? C2 C1 C7 O1 -7.6(3) . . . . ? _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.379 _refine_diff_density_min -0.377 _refine_diff_density_rms 0.073 _database_code_depnum_ccdc_archive 'CCDC 940112' ####################################################################### # # 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_Rb6coord100K _audit_creation_method SHELXL-97 _chemical_name_systematic ; rubidium hemibenzoate 6-coordinate polymorph 100 K ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H11 O4 Rb' _chemical_formula_weight 328.70 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' Rb Rb -0.9393 2.9676 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 29.347(4) _cell_length_b 3.8697(5) _cell_length_c 11.3973(16) _cell_angle_alpha 90.00 _cell_angle_beta 95.478(7) _cell_angle_gamma 90.00 _cell_volume 1288.4(3) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 4266 _cell_measurement_theta_min 3.5 _cell_measurement_theta_max 27.4 _exptl_crystal_description 'cut plate' _exptl_crystal_colour colourless _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.31 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.695 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 656 _exptl_absorpt_coefficient_mu 3.849 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.3544 _exptl_absorpt_correction_T_max 0.8308 _exptl_absorpt_process_details ; CrystalClear-SM Expert 2.0 r11 (Rigaku, 2011. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100 _diffrn_source_power 2.5 _diffrn_source_voltage 45.0 _diffrn_source_current 55.0 _diffrn_radiation_wavelength 0.71075 _diffrn_radiation_type 'Mo K\a' _diffrn_source 'Rotating Anode' _diffrn_radiation_monochromator Confocal _diffrn_measurement_specimen_support MiTeGen _diffrn_detector CCD _diffrn_measurement_device ; AFC12 (Right): Kappa 3 circle ; _diffrn_measurement_device_type ; Rigaku Saturn724+ (2x2 bin mode) ; _diffrn_detector_area_resol_mean 28.5714 _diffrn_measurement_method 'profile data from \w-scans' _diffrn_reflns_number 4341 _diffrn_reflns_av_R_equivalents 0.0222 _diffrn_reflns_av_sigmaI/netI 0.0247 _diffrn_reflns_limit_h_min -26 _diffrn_reflns_limit_h_max 38 _diffrn_reflns_limit_k_min -4 _diffrn_reflns_limit_k_max 4 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.59 _diffrn_reflns_theta_max 27.42 _reflns_number_total 1423 _reflns_number_gt 1404 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrystalClear-SM Expert 3.1 b20 (Rigaku, 20112) ; _computing_cell_refinement ; CrystalClear-SM Expert 3.1 b20 (Rigaku, 20112) ; _computing_data_reduction ; CrystalClear-SM Expert 3.1 b20 (Rigaku, 20112) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0451P)^2^+1.4121P] 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 refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1423 _refine_ls_number_parameters 108 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0253 _refine_ls_R_factor_gt 0.0250 _refine_ls_wR_factor_ref 0.0687 _refine_ls_wR_factor_gt 0.0685 _refine_ls_goodness_of_fit_ref 1.078 _refine_ls_restrained_S_all 1.078 _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 Rb1 Rb 0.0000 0.10647(6) 0.7500 0.02075(11) Uani 1 2 d S . . O1 O 0.03814(4) 0.5233(5) 1.05592(11) 0.0232(3) Uani 1 1 d . . . O2 O 0.05937(5) 0.6351(3) 0.87631(11) 0.0188(3) Uani 1 1 d . . . C1 C 0.11561(6) 0.6886(5) 1.04105(14) 0.0144(3) Uani 1 1 d . . . C2 C 0.12843(6) 0.6083(4) 1.15986(15) 0.0158(4) Uani 1 1 d . . . C3 C 0.17308(6) 0.6758(5) 1.20801(15) 0.0174(3) Uani 1 1 d . . . C4 C 0.20466(6) 0.8244(5) 1.13934(16) 0.0184(3) Uani 1 1 d . . . C5 C 0.19175(7) 0.9086(4) 1.02126(17) 0.0190(4) Uani 1 1 d . . . C6 C 0.14731(6) 0.8386(5) 0.97240(15) 0.0164(3) Uani 1 1 d . . . C7 C 0.06812(6) 0.6124(4) 0.98487(15) 0.0154(4) Uani 1 1 d . . . H1 H 0.0000 0.5000 1.0000 0.083(17) Uiso 1 2 d S . . H2 H 0.1075(8) 0.495(7) 1.210(2) 0.018(5) Uiso 1 1 d . . . H3 H 0.1822(9) 0.617(6) 1.289(2) 0.023(6) Uiso 1 1 d . . . H4 H 0.2325(10) 0.867(6) 1.167(2) 0.023(6) Uiso 1 1 d . . . H5 H 0.2126(9) 1.010(8) 0.972(2) 0.027(6) Uiso 1 1 d . . . H6 H 0.1386(10) 0.894(6) 0.895(3) 0.028(7) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Rb1 0.02380(16) 0.01771(16) 0.01871(15) 0.000 -0.00850(9) 0.000 O1 0.0122(6) 0.0408(8) 0.0161(6) 0.0010(6) -0.0006(4) -0.0043(6) O2 0.0155(6) 0.0249(7) 0.0152(6) 0.0001(4) -0.0022(5) -0.0007(5) C1 0.0123(8) 0.0150(7) 0.0152(7) -0.0016(6) -0.0012(6) 0.0012(6) C2 0.0140(8) 0.0185(9) 0.0146(7) 0.0000(5) -0.0002(6) 0.0007(6) C3 0.0147(8) 0.0208(8) 0.0161(7) -0.0018(6) -0.0026(6) 0.0017(7) C4 0.0117(8) 0.0212(8) 0.0214(8) -0.0039(7) -0.0032(6) -0.0004(7) C5 0.0164(9) 0.0196(9) 0.0211(8) -0.0003(6) 0.0031(7) -0.0015(6) C6 0.0173(8) 0.0172(8) 0.0144(7) -0.0004(6) -0.0001(6) 0.0006(7) C7 0.0135(8) 0.0162(9) 0.0158(7) -0.0009(5) -0.0021(6) 0.0006(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 Rb1 O2 2.8206(13) 2_546 ? Rb1 O2 2.8206(13) 1_545 ? Rb1 O1 2.9448(15) 5_567 ? Rb1 O1 2.9448(15) 6_565 ? Rb1 O2 2.9688(13) . ? Rb1 O2 2.9688(13) 2_556 ? Rb1 H1 3.2307 . ? O1 C7 1.298(2) . ? O1 Rb1 2.9448(15) 5_567 ? O1 H1 1.2374 . ? O2 C7 1.243(2) . ? O2 Rb1 2.8206(13) 1_565 ? C1 C6 1.398(2) . ? C1 C2 1.405(2) . ? C1 C7 1.507(2) . ? C2 C3 1.396(3) . ? C2 H2 0.98(2) . ? C3 C4 1.393(3) . ? C3 H3 0.96(3) . ? C4 C5 1.401(3) . ? C4 H4 0.86(3) . ? C5 C6 1.395(3) . ? C5 H5 0.96(3) . ? C6 H6 0.92(3) . ? 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 O2 Rb1 O2 99.42(5) 2_546 1_545 ? O2 Rb1 O1 115.94(4) 2_546 5_567 ? O2 Rb1 O1 101.06(4) 1_545 5_567 ? O2 Rb1 O1 101.06(4) 2_546 6_565 ? O2 Rb1 O1 115.94(4) 1_545 6_565 ? O1 Rb1 O1 121.77(7) 5_567 6_565 ? O2 Rb1 O2 176.74(4) 2_546 . ? O2 Rb1 O2 83.85(4) 1_545 . ? O1 Rb1 O2 63.13(4) 5_567 . ? O1 Rb1 O2 77.37(4) 6_565 . ? O2 Rb1 O2 83.85(4) 2_546 2_556 ? O2 Rb1 O2 176.74(4) 1_545 2_556 ? O1 Rb1 O2 77.37(4) 5_567 2_556 ? O1 Rb1 O2 63.13(4) 6_565 2_556 ? O2 Rb1 O2 92.89(5) . 2_556 ? O2 Rb1 O1 56.85(4) 2_546 6 ? O2 Rb1 O1 69.96(4) 1_545 6 ? O1 Rb1 O1 165.67(5) 5_567 6 ? O1 Rb1 O1 72.56(3) 6_565 6 ? O2 Rb1 O1 124.81(3) . 6 ? O2 Rb1 O1 112.14(3) 2_556 6 ? O2 Rb1 O1 69.96(4) 2_546 5_557 ? O2 Rb1 O1 56.85(4) 1_545 5_557 ? O1 Rb1 O1 72.56(3) 5_567 5_557 ? O1 Rb1 O1 165.67(5) 6_565 5_557 ? O2 Rb1 O1 112.14(3) . 5_557 ? O2 Rb1 O1 124.81(3) 2_556 5_557 ? O1 Rb1 O1 93.11(5) 6 5_557 ? O2 Rb1 C7 15.33(4) 2_546 2_546 ? O2 Rb1 C7 107.38(4) 1_545 2_546 ? O1 Rb1 C7 125.09(4) 5_567 2_546 ? O1 Rb1 C7 85.76(4) 6_565 2_546 ? O2 Rb1 C7 162.69(4) . 2_546 ? O2 Rb1 C7 75.80(4) 2_556 2_546 ? O1 Rb1 C7 51.43(4) 6 2_546 ? O1 Rb1 C7 85.15(4) 5_557 2_546 ? O2 Rb1 C7 107.38(4) 2_546 1_545 ? O2 Rb1 C7 15.33(4) 1_545 1_545 ? O1 Rb1 C7 85.76(4) 5_567 1_545 ? O1 Rb1 C7 125.09(4) 6_565 1_545 ? O2 Rb1 C7 75.80(4) . 1_545 ? O2 Rb1 C7 162.69(4) 2_556 1_545 ? O1 Rb1 C7 85.15(4) 6 1_545 ? O1 Rb1 C7 51.43(4) 5_557 1_545 ? C7 Rb1 C7 118.04(5) 2_546 1_545 ? O2 Rb1 C7 165.06(4) 2_546 . ? O2 Rb1 C7 73.21(4) 1_545 . ? O1 Rb1 C7 54.75(4) 5_567 . ? O1 Rb1 C7 93.87(4) 6_565 . ? O2 Rb1 C7 16.84(4) . . ? O2 Rb1 C7 103.61(4) 2_556 . ? O1 Rb1 C7 128.90(3) 6 . ? O1 Rb1 C7 95.30(4) 5_557 . ? C7 Rb1 C7 179.40(4) 2_546 . ? C7 Rb1 C7 62.56(3) 1_545 . ? O2 Rb1 C7 73.21(4) 2_546 2_556 ? O2 Rb1 C7 165.06(4) 1_545 2_556 ? O1 Rb1 C7 93.87(4) 5_567 2_556 ? O1 Rb1 C7 54.75(4) 6_565 2_556 ? O2 Rb1 C7 103.61(4) . 2_556 ? O2 Rb1 C7 16.84(4) 2_556 2_556 ? O1 Rb1 C7 95.30(4) 6 2_556 ? O1 Rb1 C7 128.90(3) 5_557 2_556 ? C7 Rb1 C7 62.56(3) 2_546 2_556 ? C7 Rb1 C7 179.40(4) 1_545 2_556 ? C7 Rb1 C7 116.84(5) . 2_556 ? O2 Rb1 H1 134.66 2_546 . ? O2 Rb1 H1 84.65 1_545 . ? O1 Rb1 H1 22.51 5_567 . ? O1 Rb1 H1 117.72 6_565 . ? O2 Rb1 H1 45.33 . . ? O2 Rb1 H1 93.06 2_556 . ? O1 Rb1 H1 154.33 6 . ? O1 Rb1 H1 75.35 5_557 . ? C7 Rb1 H1 146.40 2_546 . ? C7 Rb1 H1 69.66 1_545 . ? C7 Rb1 H1 33.55 . . ? C7 Rb1 H1 109.86 2_556 . ? C7 O1 Rb1 131.93(13) . 5_567 ? C7 O1 Rb1 147.72(12) . 5_557 ? Rb1 O1 Rb1 72.56(3) 5_567 5_557 ? C7 O1 H1 109.37 . . ? Rb1 O1 H1 91.85 5_567 . ? Rb1 O1 H1 86.98 5_557 . ? C7 O2 Rb1 127.80(11) . 1_565 ? C7 O2 Rb1 119.34(11) . . ? Rb1 O2 Rb1 83.85(4) 1_565 . ? C6 C1 C2 120.02(16) . . ? C6 C1 C7 118.79(15) . . ? C2 C1 C7 121.19(15) . . ? C3 C2 C1 119.48(16) . . ? C3 C2 H2 118.2(14) . . ? C1 C2 H2 122.3(14) . . ? C4 C3 C2 120.41(16) . . ? C4 C3 H3 119.8(16) . . ? C2 C3 H3 119.8(16) . . ? C3 C4 C5 120.15(17) . . ? C3 C4 H4 122.2(18) . . ? C5 C4 H4 117.6(18) . . ? C6 C5 C4 119.67(16) . . ? C6 C5 H5 118.0(15) . . ? C4 C5 H5 122.3(15) . . ? C5 C6 C1 120.26(16) . . ? C5 C6 H6 120.0(18) . . ? C1 C6 H6 119.8(18) . . ? O2 C7 O1 123.51(17) . . ? O2 C7 C1 120.28(16) . . ? O1 C7 C1 116.21(15) . . ? O2 C7 Rb1 36.87(8) . 1_565 ? O1 C7 Rb1 103.66(11) . 1_565 ? C1 C7 Rb1 128.17(11) . 1_565 ? O2 C7 Rb1 43.82(9) . . ? O1 C7 Rb1 87.69(10) . . ? C1 C7 Rb1 144.77(11) . . ? Rb1 C7 Rb1 62.56(3) 1_565 . ? _diffrn_measured_fraction_theta_max 0.978 _diffrn_reflns_theta_full 27.42 _diffrn_measured_fraction_theta_full 0.978 _refine_diff_density_max 0.591 _refine_diff_density_min -0.896 _refine_diff_density_rms 0.077 _vrf_PLAT222_Rb6coord100K ; PROBLEM:Large Non-Solvent H Uiso(max)/Uiso(min) .. 4.6 Ratio RESPONSE: H atom is located on a centre, but may be disordered between two positions to either side of the centre. ; _vrf_PLAT303_Rb6coord100K ; PROBLEM:Full Occupancy H-Atom H1 with # Connections 2.00 RESPONSE: H atom is on a centre of symmetry between two O atoms, H--O 1.24 Ang ; _database_code_depnum_ccdc_archive 'CCDC 940113' ####################################################################### # # 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_rb8coord _audit_creation_method SHELXL-97 _chemical_name_systematic ; Rubidium hemibenzoate 8 coordinate polymorph ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H11 O4 Rb' _chemical_formula_weight 328.70 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' Rb Rb -0.9393 2.9676 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 29.0315(9) _cell_length_b 6.9630(2) _cell_length_c 6.6156(2) _cell_angle_alpha 90.00 _cell_angle_beta 99.297(2) _cell_angle_gamma 90.00 _cell_volume 1319.75(7) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 8571 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.654 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 656 _exptl_absorpt_coefficient_mu 3.758 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.578 _exptl_absorpt_correction_T_max 0.746 _exptl_absorpt_process_details 'SADABS 2007/2 (Sheldrick, G.M., 2007)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker-Nonius FR591 rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ; Bruker-Nonius Roper CCD camera on \k-goniostat ; _diffrn_measurement_method '\f & \w scans' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8615 _diffrn_reflns_av_R_equivalents 0.0371 _diffrn_reflns_av_sigmaI/netI 0.0272 _diffrn_reflns_limit_h_min -37 _diffrn_reflns_limit_h_max 37 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 4.27 _diffrn_reflns_theta_max 27.49 _reflns_number_total 1510 _reflns_number_gt 1439 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Hooft, R.W.W., 1998)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' #Although determined using DirAx, the cell is refined in the HKL #package during data reduction _computing_data_reduction 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. NB The position of the hydroxyl H atom is determined by the space group, and may not real. This H atom belongs to a H bonded pair of benzoate and benzoic acid partners, which are related by symmetry of the space group. It is forced to exist by symmetry on a line and its position on that line has been refined. ; _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^)+(0.0368P)^2^+2.5073P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens mixed _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1508 _refine_ls_number_parameters 89 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0302 _refine_ls_R_factor_gt 0.0278 _refine_ls_wR_factor_ref 0.0723 _refine_ls_wR_factor_gt 0.0704 _refine_ls_goodness_of_fit_ref 1.115 _refine_ls_restrained_S_all 1.115 _refine_ls_shift/su_max 0.015 _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 Rb1 Rb 0.0000 -0.22205(4) 0.2500 0.01607(12) Uani 1 2 d S . . O1 O 0.03914(6) 0.3521(3) 0.2022(3) 0.0295(4) Uani 1 1 d . . . O2 O 0.05609(6) 0.1155(3) 0.4304(3) 0.0302(4) Uani 1 1 d . . . C1 C 0.11726(9) 0.2401(3) 0.2682(4) 0.0215(5) Uani 1 1 d . . . C2 C 0.12945(8) 0.3520(4) 0.1098(4) 0.0247(5) Uani 1 1 d . . . H2 H 0.1062 0.4235 0.0239 0.030 Uiso 1 1 calc R . . C3 C 0.17582(9) 0.3589(4) 0.0775(4) 0.0264(5) Uani 1 1 d . . . H3 H 0.1840 0.4335 -0.0315 0.032 Uiso 1 1 calc R . . C4 C 0.20977(9) 0.2569(4) 0.2047(4) 0.0244(5) Uani 1 1 d . . . H4 H 0.2414 0.2628 0.1840 0.029 Uiso 1 1 calc R . . C5 C 0.19770(9) 0.1454(4) 0.3630(4) 0.0246(5) Uani 1 1 d . . . H5 H 0.2211 0.0753 0.4496 0.029 Uiso 1 1 calc R . . C6 C 0.15148(8) 0.1364(4) 0.3948(4) 0.0231(5) Uani 1 1 d . . . H6 H 0.1433 0.0597 0.5024 0.028 Uiso 1 1 calc R . . C7 C 0.06763(9) 0.2312(3) 0.3065(4) 0.0225(5) Uani 1 1 d . . . H1 H 0.0000 0.319(10) 0.2500 0.07(2) Uiso 1 2 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 Rb1 0.02011(17) 0.01346(17) 0.01575(16) 0.000 0.00623(11) 0.000 O1 0.0201(8) 0.0320(10) 0.0366(10) 0.0065(8) 0.0055(7) 0.0010(7) O2 0.0264(9) 0.0308(11) 0.0354(10) 0.0042(8) 0.0110(8) -0.0028(7) C1 0.0224(12) 0.0195(11) 0.0229(12) -0.0033(9) 0.0049(9) -0.0020(9) C2 0.0237(12) 0.0226(12) 0.0275(12) 0.0032(10) 0.0034(9) 0.0010(9) C3 0.0276(12) 0.0261(13) 0.0271(12) 0.0017(10) 0.0095(10) -0.0023(10) C4 0.0193(11) 0.0261(13) 0.0288(13) -0.0042(10) 0.0075(10) -0.0012(9) C5 0.0232(11) 0.0233(12) 0.0268(12) -0.0008(10) 0.0027(9) 0.0007(10) C6 0.0247(12) 0.0212(12) 0.0237(11) 0.0012(9) 0.0048(9) -0.0011(9) C7 0.0219(12) 0.0221(12) 0.0237(12) -0.0016(9) 0.0037(10) -0.0030(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 Rb1 O2 2.9641(18) 6 ? Rb1 O2 2.9641(18) 5_556 ? Rb1 O2 2.9956(19) . ? Rb1 O2 2.9956(19) 2 ? Rb1 O1 3.1561(19) 5 ? Rb1 O1 3.1561(19) 6_556 ? Rb1 O1 3.210(2) 2_545 ? Rb1 O1 3.210(2) 1_545 ? Rb1 C7 3.704(2) . ? Rb1 C7 3.704(2) 2 ? Rb1 Rb1 4.5281(4) 5_556 ? Rb1 Rb1 4.5281(4) 5 ? O1 C7 1.298(3) . ? O1 Rb1 3.1561(19) 5 ? O1 Rb1 3.210(2) 1_565 ? O1 H1 1.249(13) . ? O2 C7 1.233(3) . ? O2 Rb1 2.9641(18) 5_556 ? C1 C6 1.393(4) . ? C1 C2 1.397(4) . ? C1 C7 1.504(4) . ? C2 C3 1.397(3) . ? C2 H2 0.9500 . ? C3 C4 1.385(4) . ? C3 H3 0.9500 . ? C4 C5 1.392(4) . ? C4 H4 0.9500 . ? C5 C6 1.393(3) . ? C5 H5 0.9500 . ? C6 H6 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 O2 Rb1 O2 151.02(7) 6 5_556 ? O2 Rb1 O2 76.22(4) 6 . ? O2 Rb1 O2 81.11(5) 5_556 . ? O2 Rb1 O2 81.11(5) 6 2 ? O2 Rb1 O2 76.22(4) 5_556 2 ? O2 Rb1 O2 76.61(7) . 2 ? O2 Rb1 O1 63.31(5) 6 5 ? O2 Rb1 O1 126.35(5) 5_556 5 ? O2 Rb1 O1 133.78(5) . 5 ? O2 Rb1 O1 76.01(5) 2 5 ? O2 Rb1 O1 126.35(5) 6 6_556 ? O2 Rb1 O1 63.31(5) 5_556 6_556 ? O2 Rb1 O1 76.01(5) . 6_556 ? O2 Rb1 O1 133.78(5) 2 6_556 ? O1 Rb1 O1 146.66(7) 5 6_556 ? O2 Rb1 O1 123.06(5) 6 2_545 ? O2 Rb1 O1 85.23(5) 5_556 2_545 ? O2 Rb1 O1 149.78(5) . 2_545 ? O2 Rb1 O1 125.87(5) 2 2_545 ? O1 Rb1 O1 75.49(4) 5 2_545 ? O1 Rb1 O1 73.77(5) 6_556 2_545 ? O2 Rb1 O1 85.23(5) 6 1_545 ? O2 Rb1 O1 123.06(5) 5_556 1_545 ? O2 Rb1 O1 125.87(5) . 1_545 ? O2 Rb1 O1 149.78(5) 2 1_545 ? O1 Rb1 O1 73.77(5) 5 1_545 ? O1 Rb1 O1 75.49(4) 6_556 1_545 ? O1 Rb1 O1 44.98(6) 2_545 1_545 ? O2 Rb1 C7 61.02(6) 6 . ? O2 Rb1 C7 93.34(5) 5_556 . ? O2 Rb1 C7 17.43(5) . . ? O2 Rb1 C7 67.47(5) 2 . ? O1 Rb1 C7 116.35(5) 5 . ? O1 Rb1 C7 92.57(5) 6_556 . ? O1 Rb1 C7 165.39(5) 2_545 . ? O1 Rb1 C7 127.36(5) 1_545 . ? O2 Rb1 C7 93.34(5) 6 2 ? O2 Rb1 C7 61.02(6) 5_556 2 ? O2 Rb1 C7 67.47(5) . 2 ? O2 Rb1 C7 17.43(5) 2 2 ? O1 Rb1 C7 92.57(5) 5 2 ? O1 Rb1 C7 116.35(5) 6_556 2 ? O1 Rb1 C7 127.36(5) 2_545 2 ? O1 Rb1 C7 165.39(5) 1_545 2 ? C7 Rb1 C7 63.12(8) . 2 ? O2 Rb1 Rb1 114.53(4) 6 5_556 ? O2 Rb1 Rb1 40.81(4) 5_556 5_556 ? O2 Rb1 Rb1 40.30(3) . 5_556 ? O2 Rb1 Rb1 72.00(4) 2 5_556 ? O1 Rb1 Rb1 147.75(4) 5 5_556 ? O1 Rb1 Rb1 63.00(4) 6_556 5_556 ? O1 Rb1 Rb1 121.14(3) 2_545 5_556 ? O1 Rb1 Rb1 138.14(3) 1_545 5_556 ? C7 Rb1 Rb1 53.62(4) . 5_556 ? C7 Rb1 Rb1 55.20(4) 2 5_556 ? O2 Rb1 Rb1 40.81(4) 6 5 ? O2 Rb1 Rb1 114.53(4) 5_556 5 ? O2 Rb1 Rb1 72.00(4) . 5 ? O2 Rb1 Rb1 40.30(3) 2 5 ? O1 Rb1 Rb1 63.00(4) 5 5 ? O1 Rb1 Rb1 147.75(4) 6_556 5 ? O1 Rb1 Rb1 138.14(3) 2_545 5 ? O1 Rb1 Rb1 121.14(3) 1_545 5 ? C7 Rb1 Rb1 55.20(4) . 5 ? C7 Rb1 Rb1 53.62(4) 2 5 ? Rb1 Rb1 Rb1 93.856(11) 5_556 5 ? C7 O1 Rb1 114.77(16) . 5 ? C7 O1 Rb1 138.78(16) . 1_565 ? Rb1 O1 Rb1 106.23(5) 5 1_565 ? C7 O1 H1 106(2) . . ? Rb1 O1 H1 89.1(9) 5 . ? Rb1 O1 H1 78(3) 1_565 . ? C7 O2 Rb1 123.38(16) . 5_556 ? C7 O2 Rb1 115.86(16) . . ? Rb1 O2 Rb1 98.89(5) 5_556 . ? C6 C1 C2 119.8(2) . . ? C6 C1 C7 119.1(2) . . ? C2 C1 C7 121.0(2) . . ? C1 C2 C3 120.1(2) . . ? C1 C2 H2 120.0 . . ? C3 C2 H2 120.0 . . ? C4 C3 C2 119.9(2) . . ? C4 C3 H3 120.1 . . ? C2 C3 H3 120.1 . . ? C3 C4 C5 120.1(2) . . ? C3 C4 H4 119.9 . . ? C5 C4 H4 119.9 . . ? C4 C5 C6 120.3(2) . . ? C4 C5 H5 119.9 . . ? C6 C5 H5 119.9 . . ? C1 C6 C5 119.8(2) . . ? C1 C6 H6 120.1 . . ? C5 C6 H6 120.1 . . ? O2 C7 O1 124.0(2) . . ? O2 C7 C1 120.6(2) . . ? O1 C7 C1 115.4(2) . . ? O2 C7 Rb1 46.70(13) . . ? O1 C7 Rb1 102.54(15) . . ? C1 C7 Rb1 121.67(15) . . ? 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 O2 Rb1 O2 C7 27.80(18) 6 . . . ? O2 Rb1 O2 C7 -134.0(2) 5_556 . . . ? O2 Rb1 O2 C7 -56.16(16) 2 . . . ? O1 Rb1 O2 C7 -1.1(2) 5 . . . ? O1 Rb1 O2 C7 161.44(18) 6_556 . . . ? O1 Rb1 O2 C7 161.84(16) 2_545 . . . ? O1 Rb1 O2 C7 101.36(18) 1_545 . . . ? C7 Rb1 O2 C7 -71.79(19) 2 . . . ? Rb1 Rb1 O2 C7 -134.0(2) 5_556 . . . ? Rb1 Rb1 O2 C7 -14.49(17) 5 . . . ? O2 Rb1 O2 Rb1 161.81(6) 6 . . 5_556 ? O2 Rb1 O2 Rb1 0.0 5_556 . . 5_556 ? O2 Rb1 O2 Rb1 77.85(5) 2 . . 5_556 ? O1 Rb1 O2 Rb1 132.93(5) 5 . . 5_556 ? O1 Rb1 O2 Rb1 -64.56(5) 6_556 . . 5_556 ? O1 Rb1 O2 Rb1 -64.16(11) 2_545 . . 5_556 ? O1 Rb1 O2 Rb1 -124.63(5) 1_545 . . 5_556 ? C7 Rb1 O2 Rb1 134.0(2) . . . 5_556 ? C7 Rb1 O2 Rb1 62.22(6) 2 . . 5_556 ? Rb1 Rb1 O2 Rb1 119.51(5) 5 . . 5_556 ? C6 C1 C2 C3 0.4(4) . . . . ? C7 C1 C2 C3 179.7(2) . . . . ? C1 C2 C3 C4 -0.9(4) . . . . ? C2 C3 C4 C5 0.8(4) . . . . ? C3 C4 C5 C6 -0.2(4) . . . . ? C2 C1 C6 C5 0.2(4) . . . . ? C7 C1 C6 C5 -179.1(2) . . . . ? C4 C5 C6 C1 -0.3(4) . . . . ? Rb1 O2 C7 O1 -47.6(3) 5_556 . . . ? Rb1 O2 C7 O1 74.0(3) . . . . ? Rb1 O2 C7 C1 132.04(19) 5_556 . . . ? Rb1 O2 C7 C1 -106.3(2) . . . . ? Rb1 O2 C7 Rb1 -121.7(2) 5_556 . . . ? Rb1 O1 C7 O2 -98.7(3) 5 . . . ? Rb1 O1 C7 O2 87.8(3) 1_565 . . . ? Rb1 O1 C7 C1 81.6(2) 5 . . . ? Rb1 O1 C7 C1 -91.9(3) 1_565 . . . ? Rb1 O1 C7 Rb1 -52.88(14) 5 . . . ? Rb1 O1 C7 Rb1 133.60(16) 1_565 . . . ? C6 C1 C7 O2 -9.2(4) . . . . ? C2 C1 C7 O2 171.5(2) . . . . ? C6 C1 C7 O1 170.5(2) . . . . ? C2 C1 C7 O1 -8.8(3) . . . . ? C6 C1 C7 Rb1 -64.4(3) . . . . ? C2 C1 C7 Rb1 116.3(2) . . . . ? O2 Rb1 C7 O2 -148.8(2) 6 . . . ? O2 Rb1 C7 O2 45.39(19) 5_556 . . . ? O2 Rb1 C7 O2 118.98(18) 2 . . . ? O1 Rb1 C7 O2 179.13(16) 5 . . . ? O1 Rb1 C7 O2 -18.01(18) 6_556 . . . ? O1 Rb1 C7 O2 -38.5(3) 2_545 . . . ? O1 Rb1 C7 O2 -91.67(18) 1_545 . . . ? C7 Rb1 C7 O2 100.38(19) 2 . . . ? Rb1 Rb1 C7 O2 35.29(16) 5_556 . . . ? Rb1 Rb1 C7 O2 163.15(19) 5 . . . ? O2 Rb1 C7 O1 85.96(16) 6 . . . ? O2 Rb1 C7 O1 -79.84(16) 5_556 . . . ? O2 Rb1 C7 O1 -125.2(3) . . . . ? O2 Rb1 C7 O1 -6.25(15) 2 . . . ? O1 Rb1 C7 O1 53.90(18) 5 . . . ? O1 Rb1 C7 O1 -143.24(17) 6_556 . . . ? O1 Rb1 C7 O1 -163.71(10) 2_545 . . . ? O1 Rb1 C7 O1 143.10(16) 1_545 . . . ? C7 Rb1 C7 O1 -24.85(11) 2 . . . ? Rb1 Rb1 C7 O1 -89.94(16) 5_556 . . . ? Rb1 Rb1 C7 O1 37.92(14) 5 . . . ? O2 Rb1 C7 C1 -44.84(18) 6 . . . ? O2 Rb1 C7 C1 149.35(19) 5_556 . . . ? O2 Rb1 C7 C1 104.0(3) . . . . ? O2 Rb1 C7 C1 -137.1(2) 2 . . . ? O1 Rb1 C7 C1 -76.90(19) 5 . . . ? O1 Rb1 C7 C1 85.96(19) 6_556 . . . ? O1 Rb1 C7 C1 65.5(3) 2_545 . . . ? O1 Rb1 C7 C1 12.3(2) 1_545 . . . ? C7 Rb1 C7 C1 -155.7(2) 2 . . . ? Rb1 Rb1 C7 C1 139.3(2) 5_556 . . . ? Rb1 Rb1 C7 C1 -92.88(19) 5 . . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.343 _refine_diff_density_min -0.610 _refine_diff_density_rms 0.104 _vrf_PLAT774_c:\rb8coord ; PROBLEM: Suspect X-Y Bond in CIF: RB1 -- RB1 .. 4.53 Ang. RESPONSE: Compact structure in which the Rb atoms are coordinated by 8 oxygen atoms in a network ; _vrf_PLAT303_c:\rb8coord ; PROBLEM: Full Occupancy H-Atom H1 with # Connections 2 RESPONSE: This H atom position is fixed by the space group to be equidistant between two benzoate O atoms. It is positioned on a two fold axis. This may be so, or it may be oscillating between two positions, each of which is at ca 0.85 Angstroms from one or other O atom. This H atom is thus fixed, ; _database_code_depnum_ccdc_archive 'CCDC 940114' ####################################################################### # # 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_cs3mono _audit_creation_method SHELXL-97 _chemical_name_systematic ; cesium hemibenzoate monoclinic polymorph ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H11 Cs O4' _chemical_formula_weight 376.14 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' Cs Cs -0.3680 2.1192 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 28.9095(8) _cell_length_b 7.0509(2) _cell_length_c 6.7779(2) _cell_angle_alpha 90.00 _cell_angle_beta 99.970(2) _cell_angle_gamma 90.00 _cell_volume 1360.73(7) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 12810 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.55 _exptl_crystal_size_mid 0.45 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.836 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 728 _exptl_absorpt_coefficient_mu 2.727 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.553 _exptl_absorpt_correction_T_max 0.746 _exptl_absorpt_process_details 'SADABS 2007/2 (Sheldrick, G.M., 2007)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker-Nonius FR591 rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ; Bruker-Nonius Roper CCD camera on \k-goniostat ; _diffrn_measurement_method '\f & \w scans' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11461 _diffrn_reflns_av_R_equivalents 0.0475 _diffrn_reflns_av_sigmaI/netI 0.0281 _diffrn_reflns_limit_h_min -37 _diffrn_reflns_limit_h_max 37 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 4.17 _diffrn_reflns_theta_max 27.57 _reflns_number_total 1565 _reflns_number_gt 1529 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Hooft, R.W.W., 1998)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' #Although determined using DirAx, the cell is refined in the HKL #package during data reduction _computing_data_reduction 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. NB The position of the hydroxyl H atom is determined by the space group, and may not real. This H atom belongs to a H bonded pair of benzoate and benzoic acid partners, which are related by symmetry of the space group. It is forced to exist by symmetry on a line and its position on that line has been refined. ; _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^)+(0.0148P)^2^+3.2919P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens mixed _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1565 _refine_ls_number_parameters 89 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0196 _refine_ls_R_factor_gt 0.0189 _refine_ls_wR_factor_ref 0.0459 _refine_ls_wR_factor_gt 0.0457 _refine_ls_goodness_of_fit_ref 1.083 _refine_ls_restrained_S_all 1.083 _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 Cs1 Cs 0.0000 -0.22720(2) 0.2500 0.00989(7) Uani 1 2 d S . . O1 O 0.03958(5) 0.3467(2) 0.2070(2) 0.0115(3) Uani 1 1 d . . . O2 O 0.05804(5) 0.1141(2) 0.4310(2) 0.0114(3) Uani 1 1 d . . . C1 C 0.11848(8) 0.2396(3) 0.2715(3) 0.0080(4) Uani 1 1 d . . . C2 C 0.13057(7) 0.3572(3) 0.1229(3) 0.0104(4) Uani 1 1 d . . . H2 H 0.1072 0.4320 0.0431 0.012 Uiso 1 1 calc R . . C3 C 0.17690(7) 0.3652(3) 0.0912(3) 0.0128(4) Uani 1 1 d . . . H3 H 0.1850 0.4444 -0.0109 0.015 Uiso 1 1 calc R . . C4 C 0.21129(8) 0.2566(3) 0.2097(3) 0.0116(4) Uani 1 1 d . . . H4 H 0.2429 0.2626 0.1891 0.014 Uiso 1 1 calc R . . C5 C 0.19925(7) 0.1391(3) 0.3587(3) 0.0113(4) Uani 1 1 d . . . H5 H 0.2227 0.0652 0.4395 0.014 Uiso 1 1 calc R . . C6 C 0.15294(7) 0.1302(3) 0.3888(3) 0.0095(4) Uani 1 1 d . . . H6 H 0.1447 0.0494 0.4895 0.011 Uiso 1 1 calc R . . C7 C 0.06888(7) 0.2282(3) 0.3096(3) 0.0079(4) Uani 1 1 d . . . H1 H 0.0000 0.328(10) 0.2500 0.076(19) Uiso 1 2 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 Cs1 0.01515(11) 0.00856(10) 0.00676(10) 0.000 0.00412(7) 0.000 O1 0.0096(7) 0.0124(7) 0.0128(7) 0.0023(6) 0.0029(5) 0.0013(5) O2 0.0118(7) 0.0116(7) 0.0118(7) 0.0022(5) 0.0051(6) -0.0003(5) C1 0.0089(10) 0.0088(9) 0.0067(9) -0.0028(7) 0.0026(8) -0.0013(6) C2 0.0113(9) 0.0097(9) 0.0097(9) 0.0024(7) 0.0004(7) 0.0009(7) C3 0.0142(10) 0.0131(10) 0.0120(9) 0.0022(7) 0.0052(8) -0.0025(7) C4 0.0080(10) 0.0147(10) 0.0128(10) -0.0038(7) 0.0040(8) -0.0024(7) C5 0.0111(9) 0.0115(10) 0.0107(9) -0.0008(7) 0.0006(7) 0.0021(7) C6 0.0115(9) 0.0099(9) 0.0075(8) -0.0002(7) 0.0026(7) -0.0009(7) C7 0.0084(10) 0.0083(9) 0.0071(9) -0.0042(6) 0.0016(8) -0.0020(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 Cs1 O2 3.0631(13) 5_556 ? Cs1 O2 3.0631(13) 6 ? Cs1 O2 3.0660(14) . ? Cs1 O2 3.0660(14) 2 ? Cs1 O1 3.2230(14) 6_556 ? Cs1 O1 3.2230(14) 5 ? Cs1 O1 3.2459(15) 1_545 ? Cs1 O1 3.2459(15) 2_545 ? Cs1 C7 3.7629(19) . ? Cs1 C7 3.7629(19) 2 ? Cs1 C7 3.864(2) 6 ? Cs1 C7 3.864(2) 5_556 ? O1 C7 1.302(3) . ? O1 Cs1 3.2230(14) 5 ? O1 Cs1 3.2459(15) 1_565 ? O1 H1 1.236(8) . ? O2 C7 1.229(2) . ? O2 Cs1 3.0631(13) 5_556 ? C1 C6 1.394(3) . ? C1 C2 1.395(3) . ? C1 C7 1.503(3) . ? C2 C3 1.394(3) . ? C2 H2 0.9500 . ? C3 C4 1.394(3) . ? C3 H3 0.9500 . ? C4 C5 1.396(3) . ? C4 H4 0.9500 . ? C5 C6 1.390(3) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C7 Cs1 3.864(2) 5_556 ? 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 O2 Cs1 O2 149.83(5) 5_556 6 ? O2 Cs1 O2 80.91(4) 5_556 . ? O2 Cs1 O2 75.49(3) 6 . ? O2 Cs1 O2 75.49(3) 5_556 2 ? O2 Cs1 O2 80.91(4) 6 2 ? O2 Cs1 O2 76.56(5) . 2 ? O2 Cs1 O1 62.38(4) 5_556 6_556 ? O2 Cs1 O1 126.85(4) 6 6_556 ? O2 Cs1 O1 75.05(4) . 6_556 ? O2 Cs1 O1 131.95(4) 2 6_556 ? O2 Cs1 O1 126.85(4) 5_556 5 ? O2 Cs1 O1 62.38(4) 6 5 ? O2 Cs1 O1 131.95(4) . 5 ? O2 Cs1 O1 75.05(4) 2 5 ? O1 Cs1 O1 149.69(5) 6_556 5 ? O2 Cs1 O1 123.30(4) 5_556 1_545 ? O2 Cs1 O1 86.15(4) 6 1_545 ? O2 Cs1 O1 125.83(4) . 1_545 ? O2 Cs1 O1 150.19(4) 2 1_545 ? O1 Cs1 O1 76.83(3) 6_556 1_545 ? O1 Cs1 O1 75.15(4) 5 1_545 ? O2 Cs1 O1 86.15(4) 5_556 2_545 ? O2 Cs1 O1 123.30(4) 6 2_545 ? O2 Cs1 O1 150.19(4) . 2_545 ? O2 Cs1 O1 125.83(4) 2 2_545 ? O1 Cs1 O1 75.15(4) 6_556 2_545 ? O1 Cs1 O1 76.83(3) 5 2_545 ? O1 Cs1 O1 44.49(5) 1_545 2_545 ? O2 Cs1 C7 92.67(4) 5_556 . ? O2 Cs1 C7 60.62(4) 6 . ? O2 Cs1 C7 17.14(4) . . ? O2 Cs1 C7 67.41(4) 2 . ? O1 Cs1 C7 91.53(4) 6_556 . ? O1 Cs1 C7 114.81(4) 5 . ? O1 Cs1 C7 127.68(4) 1_545 . ? O1 Cs1 C7 165.55(4) 2_545 . ? O2 Cs1 C7 60.62(4) 5_556 2 ? O2 Cs1 C7 92.67(4) 6 2 ? O2 Cs1 C7 67.41(4) . 2 ? O2 Cs1 C7 17.14(4) 2 2 ? O1 Cs1 C7 114.81(4) 6_556 2 ? O1 Cs1 C7 91.53(4) 5 2 ? O1 Cs1 C7 165.55(4) 1_545 2 ? O1 Cs1 C7 127.68(4) 2_545 2 ? C7 Cs1 C7 62.86(6) . 2 ? O2 Cs1 C7 164.63(4) 5_556 6 ? O2 Cs1 C7 15.57(4) 6 6 ? O2 Cs1 C7 89.48(4) . 6 ? O2 Cs1 C7 90.68(4) 2 6 ? O1 Cs1 C7 126.67(4) 6_556 6 ? O1 Cs1 C7 53.26(4) 5 6 ? O1 Cs1 C7 72.07(4) 1_545 6 ? O1 Cs1 C7 107.73(4) 2_545 6 ? C7 Cs1 C7 75.56(4) . 6 ? C7 Cs1 C7 104.62(4) 2 6 ? O2 Cs1 C7 15.57(4) 5_556 5_556 ? O2 Cs1 C7 164.63(4) 6 5_556 ? O2 Cs1 C7 90.68(4) . 5_556 ? O2 Cs1 C7 89.48(4) 2 5_556 ? O1 Cs1 C7 53.26(4) 6_556 5_556 ? O1 Cs1 C7 126.67(4) 5 5_556 ? O1 Cs1 C7 107.73(4) 1_545 5_556 ? O1 Cs1 C7 72.07(4) 2_545 5_556 ? C7 Cs1 C7 104.62(4) . 5_556 ? C7 Cs1 C7 75.56(4) 2 5_556 ? C7 Cs1 C7 179.79(6) 6 5_556 ? C7 O1 Cs1 115.81(11) . 5 ? C7 O1 Cs1 138.84(12) . 1_565 ? Cs1 O1 Cs1 104.85(4) 5 1_565 ? C7 O1 H1 110(2) . . ? Cs1 O1 H1 90.5(9) 5 . ? Cs1 O1 H1 74(3) 1_565 . ? C7 O2 Cs1 122.44(12) . 5_556 ? C7 O2 Cs1 115.53(12) . . ? Cs1 O2 Cs1 99.09(4) 5_556 . ? C6 C1 C2 119.79(19) . . ? C6 C1 C7 118.77(18) . . ? C2 C1 C7 121.44(19) . . ? C3 C2 C1 120.18(19) . . ? C3 C2 H2 119.9 . . ? C1 C2 H2 119.9 . . ? C2 C3 C4 119.85(19) . . ? C2 C3 H3 120.1 . . ? C4 C3 H3 120.1 . . ? C3 C4 C5 120.02(19) . . ? C3 C4 H4 120.0 . . ? C5 C4 H4 120.0 . . ? C6 C5 C4 120.00(19) . . ? C6 C5 H5 120.0 . . ? C4 C5 H5 120.0 . . ? C5 C6 C1 120.17(18) . . ? C5 C6 H6 119.9 . . ? C1 C6 H6 119.9 . . ? O2 C7 O1 124.04(19) . . ? O2 C7 C1 120.75(19) . . ? O1 C7 C1 115.20(17) . . ? O2 C7 Cs1 47.33(10) . . ? O1 C7 Cs1 101.95(12) . . ? C1 C7 Cs1 122.01(11) . . ? O2 C7 Cs1 41.99(10) . 5_556 ? O1 C7 Cs1 92.25(11) . 5_556 ? C1 C7 Cs1 140.14(13) . 5_556 ? Cs1 C7 Cs1 75.38(4) . 5_556 ? 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 O2 Cs1 O2 C7 -132.72(15) 5_556 . . . ? O2 Cs1 O2 C7 28.33(14) 6 . . . ? O2 Cs1 O2 C7 -55.59(13) 2 . . . ? O1 Cs1 O2 C7 163.59(14) 6_556 . . . ? O1 Cs1 O2 C7 -0.43(15) 5 . . . ? O1 Cs1 O2 C7 102.51(14) 1_545 . . . ? O1 Cs1 O2 C7 161.87(13) 2_545 . . . ? C7 Cs1 O2 C7 -70.86(15) 2 . . . ? C7 Cs1 O2 C7 35.24(13) 6 . . . ? C7 Cs1 O2 C7 -144.89(12) 5_556 . . . ? O2 Cs1 O2 Cs1 0.0 5_556 . . 5_556 ? O2 Cs1 O2 Cs1 161.05(4) 6 . . 5_556 ? O2 Cs1 O2 Cs1 77.13(4) 2 . . 5_556 ? O1 Cs1 O2 Cs1 -63.69(4) 6_556 . . 5_556 ? O1 Cs1 O2 Cs1 132.29(4) 5 . . 5_556 ? O1 Cs1 O2 Cs1 -124.77(4) 1_545 . . 5_556 ? O1 Cs1 O2 Cs1 -65.41(8) 2_545 . . 5_556 ? C7 Cs1 O2 Cs1 132.72(15) . . . 5_556 ? C7 Cs1 O2 Cs1 61.86(4) 2 . . 5_556 ? C7 Cs1 O2 Cs1 167.96(4) 6 . . 5_556 ? C7 Cs1 O2 Cs1 -12.17(4) 5_556 . . 5_556 ? C6 C1 C2 C3 0.2(3) . . . . ? C7 C1 C2 C3 179.84(18) . . . . ? C1 C2 C3 C4 -0.6(3) . . . . ? C2 C3 C4 C5 0.5(3) . . . . ? C3 C4 C5 C6 0.1(3) . . . . ? C4 C5 C6 C1 -0.5(3) . . . . ? C2 C1 C6 C5 0.4(3) . . . . ? C7 C1 C6 C5 -179.30(18) . . . . ? Cs1 O2 C7 O1 -47.2(2) 5_556 . . . ? Cs1 O2 C7 O1 73.6(2) . . . . ? Cs1 O2 C7 C1 132.39(15) 5_556 . . . ? Cs1 O2 C7 C1 -106.88(17) . . . . ? Cs1 O2 C7 Cs1 -120.73(15) 5_556 . . . ? Cs1 O2 C7 Cs1 120.73(15) . . . 5_556 ? Cs1 O1 C7 O2 -100.76(19) 5 . . . ? Cs1 O1 C7 O2 88.9(2) 1_565 . . . ? Cs1 O1 C7 C1 79.67(17) 5 . . . ? Cs1 O1 C7 C1 -90.7(2) 1_565 . . . ? Cs1 O1 C7 Cs1 -54.63(11) 5 . . . ? Cs1 O1 C7 Cs1 135.00(12) 1_565 . . . ? Cs1 O1 C7 Cs1 -130.16(6) 5 . . 5_556 ? Cs1 O1 C7 Cs1 59.48(16) 1_565 . . 5_556 ? C6 C1 C7 O2 -5.6(3) . . . . ? C2 C1 C7 O2 174.75(18) . . . . ? C6 C1 C7 O1 174.03(17) . . . . ? C2 C1 C7 O1 -5.7(3) . . . . ? C6 C1 C7 Cs1 -61.6(2) . . . . ? C2 C1 C7 Cs1 118.69(17) . . . . ? C6 C1 C7 Cs1 44.9(3) . . . 5_556 ? C2 C1 C7 Cs1 -134.80(18) . . . 5_556 ? O2 Cs1 C7 O2 46.57(15) 5_556 . . . ? O2 Cs1 C7 O2 -148.18(16) 6 . . . ? O2 Cs1 C7 O2 119.65(14) 2 . . . ? O1 Cs1 C7 O2 -15.84(14) 6_556 . . . ? O1 Cs1 C7 O2 179.65(13) 5 . . . ? O1 Cs1 C7 O2 -90.34(14) 1_545 . . . ? O1 Cs1 C7 O2 -38.3(2) 2_545 . . . ? C7 Cs1 C7 O2 101.42(15) 2 . . . ? C7 Cs1 C7 O2 -143.43(13) 6 . . . ? C7 Cs1 C7 O2 36.46(12) 5_556 . . . ? O2 Cs1 C7 O1 -79.10(12) 5_556 . . . ? O2 Cs1 C7 O1 86.15(12) 6 . . . ? O2 Cs1 C7 O1 -125.7(2) . . . . ? O2 Cs1 C7 O1 -6.02(11) 2 . . . ? O1 Cs1 C7 O1 -141.52(12) 6_556 . . . ? O1 Cs1 C7 O1 53.97(13) 5 . . . ? O1 Cs1 C7 O1 143.99(12) 1_545 . . . ? O1 Cs1 C7 O1 -164.00(7) 2_545 . . . ? C7 Cs1 C7 O1 -24.26(8) 2 . . . ? C7 Cs1 C7 O1 90.89(11) 6 . . . ? C7 Cs1 C7 O1 -89.21(12) 5_556 . . . ? O2 Cs1 C7 C1 150.69(15) 5_556 . . . ? O2 Cs1 C7 C1 -44.06(14) 6 . . . ? O2 Cs1 C7 C1 104.1(2) . . . . ? O2 Cs1 C7 C1 -136.23(16) 2 . . . ? O1 Cs1 C7 C1 88.27(15) 6_556 . . . ? O1 Cs1 C7 C1 -76.24(16) 5 . . . ? O1 Cs1 C7 C1 13.78(17) 1_545 . . . ? O1 Cs1 C7 C1 65.8(2) 2_545 . . . ? C7 Cs1 C7 C1 -154.47(19) 2 . . . ? C7 Cs1 C7 C1 -39.32(16) 6 . . . ? C7 Cs1 C7 C1 140.58(16) 5_556 . . . ? O2 Cs1 C7 Cs1 10.11(4) 5_556 . . 5_556 ? O2 Cs1 C7 Cs1 175.36(5) 6 . . 5_556 ? O2 Cs1 C7 Cs1 -36.46(12) . . . 5_556 ? O2 Cs1 C7 Cs1 83.19(4) 2 . . 5_556 ? O1 Cs1 C7 Cs1 -52.31(3) 6_556 . . 5_556 ? O1 Cs1 C7 Cs1 143.18(3) 5 . . 5_556 ? O1 Cs1 C7 Cs1 -126.80(4) 1_545 . . 5_556 ? O1 Cs1 C7 Cs1 -74.79(16) 2_545 . . 5_556 ? C7 Cs1 C7 Cs1 64.95(5) 2 . . 5_556 ? C7 Cs1 C7 Cs1 -179.90(3) 6 . . 5_556 ? C7 Cs1 C7 Cs1 0.0 5_556 . . 5_556 ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.615 _refine_diff_density_min -0.804 _refine_diff_density_rms 0.099 _database_code_depnum_ccdc_archive 'CCDC 940115' ####################################################################### # # 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_csortho _audit_creation_method SHELXL-97 _chemical_name_systematic ; cesium hemibenzoate orthorhombic phase ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H11 Cs O4' _chemical_formula_weight 376.14 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' Cs Cs -0.3680 2.1192 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Pbcn loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y, -z+1/2' '-x, -y, -z' 'x-1/2, y-1/2, -z-1/2' '-x-1/2, y-1/2, z' 'x, -y, z-1/2' _cell_length_a 28.3393(19) _cell_length_b 7.0215(3) _cell_length_c 6.9066(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1374.31(14) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 3550 _cell_measurement_theta_min 2.8675 _cell_measurement_theta_max 29.0716 _exptl_crystal_description 'thick plate' _exptl_crystal_colour colourless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.33 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.818 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 728 _exptl_absorpt_coefficient_mu 2.700 _exptl_absorpt_correction_T_min 0.475 _exptl_absorpt_correction_T_max 0.737 _exptl_absorpt_correction_type analytical _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. Reid. (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Sapphire3' _diffrn_detector_area_resol_mean 15.9832 _diffrn_measurement_method '\w scans' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7535 _diffrn_reflns_av_R_equivalents 0.0306 _diffrn_reflns_av_sigmaI/netI 0.0290 _diffrn_reflns_limit_h_min -37 _diffrn_reflns_limit_h_max 38 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 5 _diffrn_reflns_theta_min 2.88 _diffrn_reflns_theta_max 29.13 _reflns_number_total 1664 _reflns_number_gt 1389 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. NB The position of the hydroxyl H atom is determined by the space group, and may not real. This H atom belongs to a H bonded pair of benzoate and benzoic acid partners, which are related by symmetry of the space group. It is forced to exist by symmetry on a line and its position on that line has been refined. ; _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^)+(0.0088P)^2^+2.2155P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens mixed _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1664 _refine_ls_number_parameters 89 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0426 _refine_ls_R_factor_gt 0.0312 _refine_ls_wR_factor_ref 0.0540 _refine_ls_wR_factor_gt 0.0503 _refine_ls_goodness_of_fit_ref 1.176 _refine_ls_restrained_S_all 1.176 _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 Cs1 Cs 0.5000 0.77467(4) 0.2500 0.02046(9) Uani 1 2 d S . . O1 O 0.46027(7) 1.3491(3) 0.1789(3) 0.0205(5) Uani 1 1 d . . . O2 O 0.44213(7) 1.1176(3) 0.3870(3) 0.0211(5) Uani 1 1 d . . . C1 C 0.38128(10) 1.2395(4) 0.1846(4) 0.0149(6) Uani 1 1 d . . . C2 C 0.36796(10) 1.3703(5) 0.0441(4) 0.0190(7) Uani 1 1 d . . . H2 H 0.3906 1.4563 -0.0072 0.023 Uiso 1 1 calc R . . C3 C 0.32158(11) 1.3763(5) -0.0220(4) 0.0226(7) Uani 1 1 d . . . H3 H 0.3125 1.4656 -0.1185 0.027 Uiso 1 1 calc R . . C4 C 0.28858(11) 1.2503(5) 0.0545(4) 0.0201(7) Uani 1 1 d . . . H4 H 0.2568 1.2544 0.0112 0.024 Uiso 1 1 calc R . . C5 C 0.30200(11) 1.1191(5) 0.1935(4) 0.0204(7) Uani 1 1 d . . . H5 H 0.2794 1.0323 0.2440 0.024 Uiso 1 1 calc R . . C6 C 0.34817(10) 1.1133(4) 0.2594(4) 0.0189(6) Uani 1 1 d . . . H6 H 0.3572 1.0235 0.3554 0.023 Uiso 1 1 calc R . . C7 C 0.43108(10) 1.2305(4) 0.2596(4) 0.0167(6) Uani 1 1 d . . . H1 H 0.5000 1.334(10) 0.2500 0.09(2) Uiso 1 2 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 Cs1 0.02842(15) 0.01640(14) 0.01656(14) 0.000 -0.00431(12) 0.000 O1 0.0136(11) 0.0230(12) 0.0248(11) 0.0046(10) -0.0034(8) -0.0016(9) O2 0.0181(12) 0.0240(12) 0.0212(11) 0.0056(10) -0.0059(9) 0.0014(9) C1 0.0164(15) 0.0157(15) 0.0127(13) -0.0026(12) -0.0012(11) 0.0018(12) C2 0.0153(16) 0.0214(17) 0.0204(15) 0.0031(14) 0.0002(12) -0.0007(13) C3 0.0223(17) 0.0232(17) 0.0223(16) 0.0035(15) -0.0055(12) 0.0054(14) C4 0.0122(16) 0.0286(19) 0.0196(15) -0.0043(15) -0.0024(12) 0.0024(13) C5 0.0184(16) 0.0250(17) 0.0177(15) -0.0035(13) 0.0035(11) -0.0030(13) C6 0.0223(15) 0.0196(15) 0.0149(14) 0.0000(16) -0.0002(13) 0.0014(11) C7 0.0182(14) 0.0162(14) 0.0157(14) -0.0062(15) -0.0003(13) 0.0042(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 Cs1 O2 3.063(2) 4_655 ? Cs1 O2 3.063(2) . ? Cs1 O2 3.090(2) 5_676 ? Cs1 O2 3.090(2) 8_575 ? Cs1 O1 3.231(2) 1_545 ? Cs1 O1 3.231(2) 4_645 ? Cs1 O1 3.286(2) 5_675 ? Cs1 O1 3.286(2) 8_576 ? Cs1 C7 3.750(3) 4_655 ? Cs1 C7 3.750(3) . ? Cs1 C7 3.910(3) 8_575 ? Cs1 C7 3.910(3) 5_676 ? O1 C7 1.299(4) . ? O1 Cs1 3.231(2) 1_565 ? O1 Cs1 3.286(2) 5_675 ? O1 H1 1.233(7) . ? O2 C7 1.225(3) . ? O2 Cs1 3.090(2) 5_676 ? C1 C2 1.388(4) . ? C1 C6 1.390(4) . ? C1 C7 1.505(4) . ? C2 C3 1.392(4) . ? C2 H2 0.9500 . ? C3 C4 1.391(4) . ? C3 H3 0.9500 . ? C4 C5 1.384(4) . ? C4 H4 0.9500 . ? C5 C6 1.386(4) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C7 Cs1 3.910(3) 5_676 ? 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 O2 Cs1 O2 76.35(8) 4_655 . ? O2 Cs1 O2 76.94(5) 4_655 5_676 ? O2 Cs1 O2 80.86(6) . 5_676 ? O2 Cs1 O2 80.86(6) 4_655 8_575 ? O2 Cs1 O2 76.94(5) . 8_575 ? O2 Cs1 O2 151.66(8) 5_676 8_575 ? O2 Cs1 O1 150.08(5) 4_655 1_545 ? O2 Cs1 O1 125.98(5) . 1_545 ? O2 Cs1 O1 122.32(5) 5_676 1_545 ? O2 Cs1 O1 85.31(5) 8_575 1_545 ? O2 Cs1 O1 125.98(5) 4_655 4_645 ? O2 Cs1 O1 150.08(5) . 4_645 ? O2 Cs1 O1 85.31(5) 5_676 4_645 ? O2 Cs1 O1 122.32(5) 8_575 4_645 ? O1 Cs1 O1 44.69(7) 1_545 4_645 ? O2 Cs1 O1 75.28(5) 4_655 5_675 ? O2 Cs1 O1 132.04(5) . 5_675 ? O2 Cs1 O1 127.91(5) 5_676 5_675 ? O2 Cs1 O1 60.99(5) 8_575 5_675 ? O1 Cs1 O1 74.80(6) 1_545 5_675 ? O1 Cs1 O1 76.88(4) 4_645 5_675 ? O2 Cs1 O1 132.04(5) 4_655 8_576 ? O2 Cs1 O1 75.28(5) . 8_576 ? O2 Cs1 O1 60.99(5) 5_676 8_576 ? O2 Cs1 O1 127.91(5) 8_575 8_576 ? O1 Cs1 O1 76.88(4) 1_545 8_576 ? O1 Cs1 O1 74.80(6) 4_645 8_576 ? O1 Cs1 O1 149.34(8) 5_675 8_576 ? O2 Cs1 C7 17.21(6) 4_655 4_655 ? O2 Cs1 C7 67.25(6) . 4_655 ? O2 Cs1 C7 61.90(6) 5_676 4_655 ? O2 Cs1 C7 93.05(6) 8_575 4_655 ? O1 Cs1 C7 165.52(6) 1_545 4_655 ? O1 Cs1 C7 127.63(6) 4_645 4_655 ? O1 Cs1 C7 91.79(6) 5_675 4_655 ? O1 Cs1 C7 114.83(6) 8_576 4_655 ? O2 Cs1 C7 67.25(6) 4_655 . ? O2 Cs1 C7 17.21(6) . . ? O2 Cs1 C7 93.05(6) 5_676 . ? O2 Cs1 C7 61.90(6) 8_575 . ? O1 Cs1 C7 127.63(6) 1_545 . ? O1 Cs1 C7 165.52(6) 4_645 . ? O1 Cs1 C7 114.83(6) 5_675 . ? O1 Cs1 C7 91.79(6) 8_576 . ? C7 Cs1 C7 62.81(9) 4_655 . ? O2 Cs1 C7 90.41(5) 4_655 8_575 ? O2 Cs1 C7 90.43(5) . 8_575 ? O2 Cs1 C7 165.99(6) 5_676 8_575 ? O2 Cs1 C7 15.04(6) 8_575 8_575 ? O1 Cs1 C7 71.68(5) 1_545 8_575 ? O1 Cs1 C7 107.28(5) 4_645 8_575 ? O1 Cs1 C7 52.25(6) 5_675 8_575 ? O1 Cs1 C7 127.40(5) 8_576 8_575 ? C7 Cs1 C7 104.64(5) 4_655 8_575 ? C7 Cs1 C7 76.29(6) . 8_575 ? O2 Cs1 C7 90.43(5) 4_655 5_676 ? O2 Cs1 C7 90.41(5) . 5_676 ? O2 Cs1 C7 15.04(6) 5_676 5_676 ? O2 Cs1 C7 165.99(6) 8_575 5_676 ? O1 Cs1 C7 107.28(5) 1_545 5_676 ? O1 Cs1 C7 71.68(5) 4_645 5_676 ? O1 Cs1 C7 127.40(5) 5_675 5_676 ? O1 Cs1 C7 52.25(6) 8_576 5_676 ? C7 Cs1 C7 76.29(6) 4_655 5_676 ? C7 Cs1 C7 104.64(5) . 5_676 ? C7 Cs1 C7 178.94(8) 8_575 5_676 ? C7 O1 Cs1 138.54(18) . 1_565 ? C7 O1 Cs1 115.81(17) . 5_675 ? Cs1 O1 Cs1 105.20(6) 1_565 5_675 ? C7 O1 H1 111(2) . . ? Cs1 O1 H1 72(3) 1_565 . ? Cs1 O1 H1 91.4(9) 5_675 . ? C7 O2 Cs1 115.07(17) . . ? C7 O2 Cs1 124.06(18) . 5_676 ? Cs1 O2 Cs1 99.14(6) . 5_676 ? C2 C1 C6 119.9(3) . . ? C2 C1 C7 121.6(3) . . ? C6 C1 C7 118.6(3) . . ? C1 C2 C3 120.4(3) . . ? C1 C2 H2 119.8 . . ? C3 C2 H2 119.8 . . ? C4 C3 C2 119.4(3) . . ? C4 C3 H3 120.3 . . ? C2 C3 H3 120.3 . . ? C5 C4 C3 120.1(3) . . ? C5 C4 H4 119.9 . . ? C3 C4 H4 119.9 . . ? C4 C5 C6 120.5(3) . . ? C4 C5 H5 119.8 . . ? C6 C5 H5 119.8 . . ? C1 C6 C5 119.8(3) . . ? C1 C6 H6 120.1 . . ? C5 C6 H6 120.1 . . ? O2 C7 O1 124.1(3) . . ? O2 C7 C1 120.9(3) . . ? O1 C7 C1 115.0(3) . . ? O2 C7 Cs1 47.72(14) . . ? O1 C7 Cs1 101.99(17) . . ? C1 C7 Cs1 121.21(18) . . ? O2 C7 Cs1 40.90(14) . 5_676 ? O1 C7 Cs1 93.40(17) . 5_676 ? C1 C7 Cs1 140.10(19) . 5_676 ? Cs1 C7 Cs1 75.36(5) . 5_676 ? 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 O2 Cs1 O2 C7 55.88(18) 4_655 . . . ? O2 Cs1 O2 C7 134.6(2) 5_676 . . . ? O2 Cs1 O2 C7 -27.7(2) 8_575 . . . ? O1 Cs1 O2 C7 -101.9(2) 1_545 . . . ? O1 Cs1 O2 C7 -161.93(18) 4_645 . . . ? O1 Cs1 O2 C7 0.7(2) 5_675 . . . ? O1 Cs1 O2 C7 -163.2(2) 8_576 . . . ? C7 Cs1 O2 C7 71.3(2) 4_655 . . . ? C7 Cs1 O2 C7 -34.44(19) 8_575 . . . ? C7 Cs1 O2 C7 146.22(17) 5_676 . . . ? O2 Cs1 O2 Cs1 -78.67(6) 4_655 . . 5_676 ? O2 Cs1 O2 Cs1 0.0 5_676 . . 5_676 ? O2 Cs1 O2 Cs1 -162.27(6) 8_575 . . 5_676 ? O1 Cs1 O2 Cs1 123.53(6) 1_545 . . 5_676 ? O1 Cs1 O2 Cs1 63.52(12) 4_645 . . 5_676 ? O1 Cs1 O2 Cs1 -133.85(6) 5_675 . . 5_676 ? O1 Cs1 O2 Cs1 62.25(6) 8_576 . . 5_676 ? C7 Cs1 O2 Cs1 -63.27(6) 4_655 . . 5_676 ? C7 Cs1 O2 Cs1 -134.6(2) . . . 5_676 ? C7 Cs1 O2 Cs1 -168.99(6) 8_575 . . 5_676 ? C7 Cs1 O2 Cs1 11.67(6) 5_676 . . 5_676 ? C6 C1 C2 C3 0.1(5) . . . . ? C7 C1 C2 C3 -179.7(3) . . . . ? C1 C2 C3 C4 0.3(5) . . . . ? C2 C3 C4 C5 -0.7(5) . . . . ? C3 C4 C5 C6 0.8(5) . . . . ? C2 C1 C6 C5 -0.1(4) . . . . ? C7 C1 C6 C5 179.7(3) . . . . ? C4 C5 C6 C1 -0.4(4) . . . . ? Cs1 O2 C7 O1 -74.0(3) . . . . ? Cs1 O2 C7 O1 47.9(4) 5_676 . . . ? Cs1 O2 C7 C1 105.8(3) . . . . ? Cs1 O2 C7 C1 -132.4(2) 5_676 . . . ? Cs1 O2 C7 Cs1 121.9(2) 5_676 . . . ? Cs1 O2 C7 Cs1 -121.9(2) . . . 5_676 ? Cs1 O1 C7 O2 -88.0(3) 1_565 . . . ? Cs1 O1 C7 O2 101.2(3) 5_675 . . . ? Cs1 O1 C7 C1 92.3(3) 1_565 . . . ? Cs1 O1 C7 C1 -78.6(2) 5_675 . . . ? Cs1 O1 C7 Cs1 -134.62(18) 1_565 . . . ? Cs1 O1 C7 Cs1 54.57(16) 5_675 . . . ? Cs1 O1 C7 Cs1 -58.9(2) 1_565 . . 5_676 ? Cs1 O1 C7 Cs1 130.32(9) 5_675 . . 5_676 ? C2 C1 C7 O2 178.2(3) . . . . ? C6 C1 C7 O2 -1.6(4) . . . . ? C2 C1 C7 O1 -2.1(4) . . . . ? C6 C1 C7 O1 178.1(3) . . . . ? C2 C1 C7 Cs1 -125.5(3) . . . . ? C6 C1 C7 Cs1 54.7(3) . . . . ? C2 C1 C7 Cs1 129.2(3) . . . 5_676 ? C6 C1 C7 Cs1 -50.6(4) . . . 5_676 ? O2 Cs1 C7 O2 -119.3(2) 4_655 . . . ? O2 Cs1 C7 O2 -44.8(2) 5_676 . . . ? O2 Cs1 C7 O2 149.1(2) 8_575 . . . ? O1 Cs1 C7 O2 91.0(2) 1_545 . . . ? O1 Cs1 C7 O2 38.2(4) 4_645 . . . ? O1 Cs1 C7 O2 -179.43(18) 5_675 . . . ? O1 Cs1 C7 O2 16.2(2) 8_576 . . . ? C7 Cs1 C7 O2 -100.9(2) 4_655 . . . ? C7 Cs1 C7 O2 144.40(19) 8_575 . . . ? C7 Cs1 C7 O2 -35.08(18) 5_676 . . . ? O2 Cs1 C7 O1 6.23(16) 4_655 . . . ? O2 Cs1 C7 O1 125.5(3) . . . . ? O2 Cs1 C7 O1 80.70(17) 5_676 . . . ? O2 Cs1 C7 O1 -85.41(18) 8_575 . . . ? O1 Cs1 C7 O1 -143.48(18) 1_545 . . . ? O1 Cs1 C7 O1 163.72(11) 4_645 . . . ? O1 Cs1 C7 O1 -53.9(2) 5_675 . . . ? O1 Cs1 C7 O1 141.74(19) 8_576 . . . ? C7 Cs1 C7 O1 24.59(12) 4_655 . . . ? C7 Cs1 C7 O1 -90.10(17) 8_575 . . . ? C7 Cs1 C7 O1 90.42(17) 5_676 . . . ? O2 Cs1 C7 C1 135.6(2) 4_655 . . . ? O2 Cs1 C7 C1 -105.2(3) . . . . ? O2 Cs1 C7 C1 -150.0(2) 5_676 . . . ? O2 Cs1 C7 C1 43.9(2) 8_575 . . . ? O1 Cs1 C7 C1 -14.1(2) 1_545 . . . ? O1 Cs1 C7 C1 -66.9(3) 4_645 . . . ? O1 Cs1 C7 C1 75.4(2) 5_675 . . . ? O1 Cs1 C7 C1 -88.9(2) 8_576 . . . ? C7 Cs1 C7 C1 153.9(3) 4_655 . . . ? C7 Cs1 C7 C1 39.2(2) 8_575 . . . ? C7 Cs1 C7 C1 -140.2(2) 5_676 . . . ? O2 Cs1 C7 Cs1 -84.19(5) 4_655 . . 5_676 ? O2 Cs1 C7 Cs1 35.08(18) . . . 5_676 ? O2 Cs1 C7 Cs1 -9.72(5) 5_676 . . 5_676 ? O2 Cs1 C7 Cs1 -175.83(7) 8_575 . . 5_676 ? O1 Cs1 C7 Cs1 126.10(5) 1_545 . . 5_676 ? O1 Cs1 C7 Cs1 73.3(2) 4_645 . . 5_676 ? O1 Cs1 C7 Cs1 -144.35(5) 5_675 . . 5_676 ? O1 Cs1 C7 Cs1 51.32(5) 8_576 . . 5_676 ? C7 Cs1 C7 Cs1 -65.83(7) 4_655 . . 5_676 ? C7 Cs1 C7 Cs1 179.48(4) 8_575 . . 5_676 ? C7 Cs1 C7 Cs1 0.0 5_676 . . 5_676 ? _diffrn_measured_fraction_theta_max 0.898 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.661 _refine_diff_density_min -0.449 _refine_diff_density_rms 0.092 _database_code_depnum_ccdc_archive 'CCDC 940116'