# 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_global data_datam #TrackingRef 'BAK21.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'Potassium hydrogen bis(benzoate)' _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 29.585(13) _cell_length_b 3.8211(18) _cell_length_c 11.156(5) _cell_angle_alpha 90.00 _cell_angle_beta 97.327(5) _cell_angle_gamma 90.00 _cell_volume 1250.8(10) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.17 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.499 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 584 _exptl_absorpt_coefficient_mu 0.431 _exptl_absorpt_correction_type Multi-Scan _exptl_absorpt_correction_T_min 0.9074 _exptl_absorpt_correction_T_max 0.9303 _exptl_absorpt_process_details 'SADABS (G. Sheldrick, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Apex II platform CCD' _diffrn_measurement_method 'Omega and Phi scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5513 _diffrn_reflns_av_R_equivalents 0.1254 _diffrn_reflns_av_sigmaI/netI 0.0639 _diffrn_reflns_limit_h_min -34 _diffrn_reflns_limit_h_max 34 _diffrn_reflns_limit_k_min -4 _diffrn_reflns_limit_k_max 4 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.39 _diffrn_reflns_theta_max 25.07 _reflns_number_total 1112 _reflns_number_gt 992 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker Apex2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0596P)^2^+2.3533P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1112 _refine_ls_number_parameters 108 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0548 _refine_ls_R_factor_gt 0.0494 _refine_ls_wR_factor_ref 0.1357 _refine_ls_wR_factor_gt 0.1323 _refine_ls_goodness_of_fit_ref 1.122 _refine_ls_restrained_S_all 1.122 _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 K1 K 0.5000 0.1764(2) 0.7500 0.0313(3) Uani 1 2 d S . . O71 O 0.55466(6) -0.3000(5) 0.87335(17) 0.0306(5) Uani 1 1 d . . . C7 C 0.56599(9) -0.3454(7) 0.9824(2) 0.0267(6) Uani 1 1 d . . . C1 C 0.61404(9) -0.2884(7) 1.0383(2) 0.0241(6) Uani 1 1 d . . . C5 C 0.67350(10) -0.3405(7) 1.2054(3) 0.0300(6) Uani 1 1 d . . . C2 C 0.64510(10) -0.1393(7) 0.9695(3) 0.0276(6) Uani 1 1 d . . . C4 C 0.70418(9) -0.1937(8) 1.1364(3) 0.0318(7) Uani 1 1 d . . . C6 C 0.62847(9) -0.3878(7) 1.1571(3) 0.0271(6) Uani 1 1 d . . . C3 C 0.69000(10) -0.0916(7) 1.0183(3) 0.0308(7) Uani 1 1 d . . . O72 O 0.53793(6) -0.4510(6) 1.05474(17) 0.0360(5) Uani 1 1 d . . . H4 H 0.7354(12) -0.168(8) 1.168(3) 0.031(8) Uiso 1 1 d . . . H6 H 0.6076(10) -0.492(9) 1.201(3) 0.027(7) Uiso 1 1 d . . . H3 H 0.7114(12) 0.005(10) 0.971(3) 0.039(8) Uiso 1 1 d . . . H5 H 0.6824(11) -0.412(10) 1.290(3) 0.044(9) Uiso 1 1 d . . . H2 H 0.6355(11) -0.075(9) 0.888(3) 0.038(9) Uiso 1 1 d . . . H72 H 0.5000 -0.5000 1.0000 0.057(15) 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 K1 0.0408(5) 0.0247(5) 0.0269(5) 0.000 -0.0012(3) 0.000 O71 0.0334(11) 0.0323(11) 0.0251(10) 0.0014(8) -0.0005(7) -0.0025(8) C7 0.0335(15) 0.0194(13) 0.0271(14) -0.0022(11) 0.0038(11) 0.0000(11) C1 0.0311(14) 0.0155(12) 0.0262(14) -0.0035(10) 0.0049(10) 0.0011(10) C5 0.0350(15) 0.0260(14) 0.0284(15) -0.0023(12) 0.0019(11) 0.0033(11) C2 0.0353(15) 0.0216(13) 0.0267(14) -0.0004(11) 0.0070(11) -0.0003(11) C4 0.0259(14) 0.0287(15) 0.0402(16) -0.0042(13) 0.0025(12) -0.0006(12) C6 0.0307(15) 0.0230(13) 0.0285(14) -0.0010(11) 0.0074(11) -0.0005(11) C3 0.0321(15) 0.0250(14) 0.0371(16) -0.0007(12) 0.0109(12) -0.0029(11) O72 0.0289(10) 0.0517(13) 0.0276(10) 0.0016(9) 0.0041(8) -0.0071(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 K1 O71 2.694(2) 2_656 ? K1 O71 2.694(2) . ? K1 O72 2.780(2) 5_657 ? K1 O72 2.780(2) 6 ? K1 O71 2.818(2) 1_565 ? K1 O71 2.818(2) 2_666 ? K1 K1 3.8211(18) 1_545 ? O71 C7 1.232(3) . ? O71 K1 2.818(2) 1_545 ? C7 O72 1.294(3) . ? C7 C1 1.494(4) . ? C1 C6 1.392(4) . ? C1 C2 1.392(4) . ? C5 C4 1.382(4) . ? C5 C6 1.384(4) . ? C2 C3 1.382(4) . ? C4 C3 1.386(4) . ? O72 K1 2.780(2) 5_657 ? 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 O71 K1 O71 94.95(9) 2_656 . ? O71 K1 O72 112.30(6) 2_656 5_657 ? O71 K1 O72 97.51(7) . 5_657 ? O71 K1 O72 97.52(7) 2_656 6 ? O71 K1 O72 112.30(6) . 6 ? O72 K1 O72 135.65(10) 5_657 6 ? O71 K1 O71 177.30(6) 2_656 1_565 ? O71 K1 O71 87.74(6) . 1_565 ? O72 K1 O71 67.25(6) 5_657 1_565 ? O72 K1 O71 81.42(7) 6 1_565 ? O71 K1 O71 87.74(6) 2_656 2_666 ? O71 K1 O71 177.30(6) . 2_666 ? O72 K1 O71 81.42(7) 5_657 2_666 ? O72 K1 O71 67.25(6) 6 2_666 ? O71 K1 O71 89.56(9) 1_565 2_666 ? O71 K1 K1 47.48(5) 2_656 1_545 ? O71 K1 K1 47.48(5) . 1_545 ? O72 K1 K1 112.17(5) 5_657 1_545 ? O72 K1 K1 112.17(5) 6 1_545 ? O71 K1 K1 135.22(4) 1_565 1_545 ? O71 K1 K1 135.22(4) 2_666 1_545 ? C7 O71 K1 132.04(17) . . ? C7 O71 K1 116.68(17) . 1_545 ? K1 O71 K1 87.74(6) . 1_545 ? O71 C7 O72 123.0(2) . . ? O71 C7 C1 121.1(2) . . ? O72 C7 C1 115.9(2) . . ? C6 C1 C2 119.5(2) . . ? C6 C1 C7 121.2(2) . . ? C2 C1 C7 119.3(2) . . ? C4 C5 C6 120.2(3) . . ? C3 C2 C1 120.4(3) . . ? C5 C4 C3 120.2(3) . . ? C5 C6 C1 119.9(3) . . ? C2 C3 C4 119.8(3) . . ? C7 O72 K1 136.58(18) . 5_657 ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.07 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.401 _refine_diff_density_min -0.371 _refine_diff_density_rms 0.075 _database_code_depnum_ccdc_archive 'CCDC 918822' ####################################################################### # # 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_global # Attachment 'BANH411.cif' data_datam2 #TrackingRef 'BANH411.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'Ammonium benzoate' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C7 H9 N O2' _chemical_formula_weight 139.15 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pbca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 6.8750(11) _cell_length_b 6.9872(11) _cell_length_c 30.188(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1450.2(4) _cell_formula_units_Z 8 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 1288 _cell_measurement_theta_min 0.980 _cell_measurement_theta_max 0.989 _exptl_crystal_description Plates _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.275 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 592 _exptl_absorpt_coefficient_mu 0.094 _exptl_absorpt_correction_type Multi-Scan _exptl_absorpt_correction_T_min 0.9805 _exptl_absorpt_correction_T_max 0.9888 _exptl_absorpt_process_details 'SADABS (G. Sheldrick, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Apex II platform CCD' _diffrn_measurement_method 'Omega and Phi scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12652 _diffrn_reflns_av_R_equivalents 0.0684 _diffrn_reflns_av_sigmaI/netI 0.0276 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -35 _diffrn_reflns_limit_l_max 35 _diffrn_reflns_theta_min 1.35 _diffrn_reflns_theta_max 25.04 _reflns_number_total 1288 _reflns_number_gt 1076 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker Apex2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0320P)^2^+0.6652P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1288 _refine_ls_number_parameters 127 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0552 _refine_ls_R_factor_gt 0.0428 _refine_ls_wR_factor_ref 0.0916 _refine_ls_wR_factor_gt 0.0863 _refine_ls_goodness_of_fit_ref 1.094 _refine_ls_restrained_S_all 1.094 _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 O12 O 0.14401(16) 0.89156(17) 0.43214(4) 0.0332(3) Uani 1 1 d . . . O11 O -0.08863(17) 0.68343(19) 0.44960(4) 0.0394(4) Uani 1 1 d . . . C6 C 0.1318(3) 0.7153(2) 0.29963(6) 0.0312(4) Uani 1 1 d . . . C7 C 0.1403(2) 0.7749(2) 0.34336(6) 0.0282(4) Uani 1 1 d . . . C3 C -0.1210(2) 0.5616(2) 0.36136(6) 0.0298(4) Uani 1 1 d . . . C2 C 0.0141(2) 0.6986(2) 0.37466(5) 0.0251(4) Uani 1 1 d . . . C5 C -0.0030(3) 0.5796(2) 0.28662(6) 0.0329(4) Uani 1 1 d . . . C4 C -0.1296(3) 0.5029(3) 0.31752(6) 0.0354(5) Uani 1 1 d . . . C1 C 0.0246(2) 0.7630(2) 0.42206(6) 0.0276(4) Uani 1 1 d . . . N1 N -0.0065(2) 1.2378(3) 0.46275(5) 0.0316(4) Uani 1 1 d . . . H7 H 0.234(3) 0.870(3) 0.3539(6) 0.034(5) Uiso 1 1 d . . . H5 H -0.009(3) 0.540(2) 0.2551(6) 0.030(4) Uiso 1 1 d . . . H3 H -0.208(3) 0.512(3) 0.3839(6) 0.037(5) Uiso 1 1 d . . . H4 H -0.222(3) 0.409(3) 0.3080(6) 0.040(5) Uiso 1 1 d . . . H6 H 0.222(3) 0.769(3) 0.2780(6) 0.034(5) Uiso 1 1 d . . . H3N H 0.046(3) 1.123(4) 0.4540(7) 0.066(7) Uiso 1 1 d . . . H2N H -0.142(4) 1.236(3) 0.4573(7) 0.060(7) Uiso 1 1 d . . . H1N H 0.053(4) 1.333(4) 0.4464(8) 0.077(8) Uiso 1 1 d . . . H4N H 0.017(3) 1.261(3) 0.4977(8) 0.056(6) 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 O12 0.0310(6) 0.0315(6) 0.0372(7) -0.0082(6) -0.0034(5) 0.0005(5) O11 0.0332(7) 0.0554(9) 0.0295(7) -0.0008(6) 0.0035(5) -0.0063(6) C6 0.0338(10) 0.0298(10) 0.0300(10) 0.0037(7) 0.0036(8) 0.0018(8) C7 0.0271(9) 0.0242(9) 0.0334(10) 0.0009(7) -0.0013(7) -0.0006(8) C3 0.0273(9) 0.0299(9) 0.0322(10) 0.0016(8) -0.0008(8) -0.0026(8) C2 0.0225(8) 0.0225(8) 0.0302(9) 0.0015(7) -0.0024(7) 0.0043(6) C5 0.0394(10) 0.0306(10) 0.0287(9) -0.0038(8) -0.0041(8) 0.0071(8) C4 0.0355(10) 0.0312(10) 0.0395(11) -0.0028(8) -0.0087(8) -0.0037(8) C1 0.0216(8) 0.0282(9) 0.0330(10) -0.0005(8) -0.0019(7) 0.0053(7) N1 0.0316(9) 0.0317(9) 0.0316(9) -0.0012(7) 0.0001(7) -0.0024(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 O12 C1 1.254(2) . ? O11 C1 1.267(2) . ? C6 C5 1.383(2) . ? C6 C7 1.385(2) . ? C6 H6 0.976(18) . ? C7 C2 1.389(2) . ? C7 H7 0.981(19) . ? C3 C4 1.387(3) . ? C3 C2 1.393(2) . ? C3 H3 0.969(18) . ? C2 C1 1.502(2) . ? C5 C4 1.384(3) . ? C5 H5 0.992(18) . ? C4 H4 0.96(2) . ? N1 H3N 0.92(3) . ? N1 H2N 0.94(2) . ? N1 H1N 0.92(3) . ? N1 H4N 1.08(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C5 C6 C7 120.34(17) . . ? C5 C6 H6 120.1(11) . . ? C7 C6 H6 119.6(11) . . ? C6 C7 C2 120.42(16) . . ? C6 C7 H7 122.7(10) . . ? C2 C7 H7 116.9(10) . . ? C4 C3 C2 120.44(16) . . ? C4 C3 H3 122.6(11) . . ? C2 C3 H3 116.9(11) . . ? C7 C2 C3 118.95(16) . . ? C7 C2 C1 120.23(15) . . ? C3 C2 C1 120.83(15) . . ? C6 C5 C4 119.71(17) . . ? C6 C5 H5 119.3(10) . . ? C4 C5 H5 121.0(10) . . ? C5 C4 C3 120.14(17) . . ? C5 C4 H4 118.7(11) . . ? C3 C4 H4 121.2(11) . . ? O12 C1 O11 123.85(16) . . ? O12 C1 C2 118.49(15) . . ? O11 C1 C2 117.66(15) . . ? H3N N1 H2N 109(2) . . ? H3N N1 H1N 108(2) . . ? H2N N1 H1N 111(2) . . ? H3N N1 H4N 110.6(18) . . ? H2N N1 H4N 108.7(17) . . ? H1N N1 H4N 110.4(19) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.04 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.132 _refine_diff_density_min -0.151 _refine_diff_density_rms 0.036 _database_code_depnum_ccdc_archive 'CCDC 918823' ####################################################################### # # 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_global # Attachment 'BANH421.cif' data_4 #TrackingRef 'BANH421.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'Ammonium hydrogen bis(benzoate)' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H15 N O4' _chemical_formula_weight 261.27 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' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 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 29.234(10) _cell_length_b 3.8543(13) _cell_length_c 11.408(4) _cell_angle_alpha 90.00 _cell_angle_beta 94.455(5) _cell_angle_gamma 90.00 _cell_volume 1281.5(8) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description Plates _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.354 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 552 _exptl_absorpt_coefficient_mu 0.100 _exptl_absorpt_correction_type Multi-Scan _exptl_absorpt_correction_T_min 0.9755 _exptl_absorpt_correction_T_max 0.9842 _exptl_absorpt_process_details 'SADABS (G. Sheldrick, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Apex II platform CCD' _diffrn_measurement_method 'Omega and Phi scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5543 _diffrn_reflns_av_R_equivalents 0.2046 _diffrn_reflns_av_sigmaI/netI 0.1047 _diffrn_reflns_limit_h_min -34 _diffrn_reflns_limit_h_max 34 _diffrn_reflns_limit_k_min -4 _diffrn_reflns_limit_k_max 4 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.40 _diffrn_reflns_theta_max 25.05 _reflns_number_total 1143 _reflns_number_gt 841 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker Apex2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0255P)^2^+0.9545P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1143 _refine_ls_number_parameters 116 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0928 _refine_ls_R_factor_gt 0.0616 _refine_ls_wR_factor_ref 0.1545 _refine_ls_wR_factor_gt 0.1381 _refine_ls_goodness_of_fit_ref 1.080 _refine_ls_restrained_S_all 1.080 _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 O2 O 0.03750(6) 0.0361(5) 0.05617(15) 0.0367(6) Uani 1 1 d . . . O3 O 0.06072(7) 0.1576(5) -0.12020(15) 0.0390(6) Uani 1 1 d . . . C3 C 0.19172(10) 0.4100(7) 0.0244(3) 0.0363(7) Uani 1 1 d . . . C4 C 0.20390(10) 0.3212(7) 0.1406(3) 0.0367(7) Uani 1 1 d . . . C7 C 0.14805(10) 0.3491(7) -0.0238(3) 0.0323(7) Uani 1 1 d . . . C8 C 0.17210(9) 0.1723(7) 0.2077(2) 0.0328(7) Uani 1 1 d . . . C10 C 0.12771(10) 0.1121(7) 0.1606(2) 0.0297(7) Uani 1 1 d . . . C11 C 0.06856(9) 0.1292(6) -0.0127(2) 0.0296(7) Uani 1 1 d . . . C13 C 0.11564(9) 0.1970(6) 0.0435(2) 0.0291(7) Uani 1 1 d . . . N1 N 0.0000 0.4081(11) 0.2500 0.0371(9) Uani 1 2 d S . . H1N H 0.0162(12) 0.266(11) 0.200(3) 0.062(10) Uiso 1 1 d . . . H8 H 0.1800(10) 0.102(7) 0.289(3) 0.036(7) Uiso 1 1 d . . . H4 H 0.2354(10) 0.363(7) 0.176(2) 0.033(7) Uiso 1 1 d . . . H2O H 0.0000 0.0000 0.0000 0.087(17) Uiso 1 2 d S . . H7 H 0.1380(9) 0.403(7) -0.100(3) 0.035(8) Uiso 1 1 d . . . H3 H 0.2151(10) 0.526(8) -0.019(3) 0.038(7) Uiso 1 1 d . . . H10 H 0.1052(9) 0.012(7) 0.202(2) 0.028(7) Uiso 1 1 d . . . H2N H -0.0203(11) 0.539(10) 0.213(3) 0.056(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 O2 0.0358(11) 0.0492(13) 0.0253(10) -0.0014(9) 0.0035(8) -0.0048(9) O3 0.0450(12) 0.0502(13) 0.0213(10) 0.0012(8) -0.0005(8) 0.0031(10) C3 0.0397(18) 0.0299(15) 0.0404(16) -0.0007(13) 0.0100(13) -0.0050(14) C4 0.0353(17) 0.0320(17) 0.0424(17) -0.0089(13) -0.0002(13) -0.0020(13) C7 0.0423(17) 0.0282(15) 0.0264(15) 0.0028(11) 0.0036(12) -0.0006(13) C8 0.0380(17) 0.0320(16) 0.0283(15) -0.0041(12) 0.0018(12) 0.0045(12) C10 0.0363(16) 0.0271(14) 0.0262(14) 0.0001(11) 0.0047(12) 0.0010(13) C11 0.0390(16) 0.0240(14) 0.0254(14) -0.0015(11) 0.0008(11) 0.0046(12) C13 0.0369(16) 0.0221(14) 0.0282(14) -0.0007(11) 0.0024(11) 0.0029(12) N1 0.048(2) 0.035(2) 0.0270(19) 0.000 -0.0037(18) 0.000 _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 O2 C11 1.296(3) . ? O2 H2O 1.2340(18) . ? O3 C11 1.235(3) . ? C3 C7 1.371(4) . ? C3 C4 1.388(4) . ? C3 H3 0.98(3) . ? C4 C8 1.375(4) . ? C4 H4 0.99(3) . ? C7 C13 1.394(4) . ? C7 H7 0.92(3) . ? C8 C10 1.385(4) . ? C8 H8 0.98(3) . ? C10 C13 1.394(4) . ? C10 H10 0.92(3) . ? C11 C13 1.495(4) . ? N1 H1N 0.94(4) . ? N1 H2N 0.87(4) . ? 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 C11 O2 H2O 110.64(17) . . ? C7 C3 C4 120.2(3) . . ? C7 C3 H3 122.6(17) . . ? C4 C3 H3 117.2(17) . . ? C8 C4 C3 120.0(3) . . ? C8 C4 H4 119.3(16) . . ? C3 C4 H4 120.7(16) . . ? C3 C7 C13 120.2(3) . . ? C3 C7 H7 124.0(17) . . ? C13 C7 H7 115.8(17) . . ? C4 C8 C10 120.5(3) . . ? C4 C8 H8 121.7(17) . . ? C10 C8 H8 117.8(16) . . ? C8 C10 C13 119.5(3) . . ? C8 C10 H10 123.7(16) . . ? C13 C10 H10 116.8(16) . . ? O3 C11 O2 122.8(2) . . ? O3 C11 C13 120.2(3) . . ? O2 C11 C13 117.0(2) . . ? C7 C13 C10 119.6(3) . . ? C7 C13 C11 118.7(2) . . ? C10 C13 C11 121.7(3) . . ? H1N N1 H2N 114(3) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C7 C3 C4 C8 -0.1(4) . . . . ? C4 C3 C7 C13 -0.1(4) . . . . ? C3 C4 C8 C10 -0.5(4) . . . . ? C4 C8 C10 C13 1.4(4) . . . . ? C3 C7 C13 C10 1.0(4) . . . . ? C3 C7 C13 C11 -179.0(2) . . . . ? C8 C10 C13 C7 -1.6(4) . . . . ? C8 C10 C13 C11 178.4(2) . . . . ? O3 C11 C13 C7 11.0(4) . . . . ? O2 C11 C13 C7 -170.1(2) . . . . ? O3 C11 C13 C10 -169.1(2) . . . . ? O2 C11 C13 C10 9.9(4) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.05 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.188 _refine_diff_density_min -0.194 _refine_diff_density_rms 0.054 _database_code_depnum_ccdc_archive 'CCDC 918824' ####################################################################### # # 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_global # Attachment 'BANa31.cif' data_datam3 #TrackingRef 'BANa31.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'Sodium dihydrogen tris(benzoate)' _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 5.8207(11) _cell_length_b 14.460(3) _cell_length_c 22.090(4) _cell_angle_alpha 90.00 _cell_angle_beta 97.084(3) _cell_angle_gamma 90.00 _cell_volume 1845.0(6) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description Blocks _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.19 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.398 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 808 _exptl_absorpt_coefficient_mu 0.122 _exptl_absorpt_correction_type Multi-Scan _exptl_absorpt_correction_T_min 0.9620 _exptl_absorpt_correction_T_max 0.9772 _exptl_absorpt_process_details 'SADABS (G. Sheldrick, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Apex II platform CCD' _diffrn_measurement_method 'Omega and Phi scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 17738 _diffrn_reflns_av_R_equivalents 0.1327 _diffrn_reflns_av_sigmaI/netI 0.0650 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 1.69 _diffrn_reflns_theta_max 25.08 _reflns_number_total 3266 _reflns_number_gt 2511 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker Apex2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0475P)^2^+0.5071P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3266 _refine_ls_number_parameters 321 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0634 _refine_ls_R_factor_gt 0.0437 _refine_ls_wR_factor_ref 0.1159 _refine_ls_wR_factor_gt 0.1055 _refine_ls_goodness_of_fit_ref 1.031 _refine_ls_restrained_S_all 1.031 _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 Na1 Na 0.08963(12) 0.88489(5) 0.01320(3) 0.0294(2) Uani 1 1 d . . . O31 O 0.2103(2) 1.03229(9) 0.04724(6) 0.0266(3) Uani 1 1 d . . . O21 O 0.3548(2) 0.80269(10) 0.08180(6) 0.0303(4) Uani 1 1 d . . . O200 O 0.4785(2) 0.88121(10) -0.04054(6) 0.0282(3) Uani 1 1 d . . . C32 C 0.4959(3) 1.03989(13) 0.13393(8) 0.0222(4) Uani 1 1 d . . . O12 O 0.0057(2) 0.75317(10) -0.04681(7) 0.0365(4) Uani 1 1 d . . . O100 O -0.2906(2) 0.84165(11) 0.06294(6) 0.0320(4) Uani 1 1 d . . . C31 C 0.4006(3) 1.06416(13) 0.06951(8) 0.0217(4) Uani 1 1 d . . . O11 O 0.3344(3) 0.71578(12) -0.08339(8) 0.0417(4) Uani 1 1 d . . . C22 C 0.6644(3) 0.78556(13) 0.16193(9) 0.0236(4) Uani 1 1 d . . . C37 C 0.7226(3) 1.06138(14) 0.15784(9) 0.0262(5) Uani 1 1 d . . . C33 C 0.3516(3) 0.99767(14) 0.17147(9) 0.0267(5) Uani 1 1 d . . . C36 C 0.8014(4) 1.04132(16) 0.21822(9) 0.0303(5) Uani 1 1 d . . . C21 C 0.5618(3) 0.81024(13) 0.09865(9) 0.0241(4) Uani 1 1 d . . . C35 C 0.6553(4) 0.99962(16) 0.25507(9) 0.0328(5) Uani 1 1 d . . . C24 C 0.6029(4) 0.72572(16) 0.26038(10) 0.0341(5) Uani 1 1 d . . . C11 C 0.1263(3) 0.69655(15) -0.06883(9) 0.0288(5) Uani 1 1 d . . . C27 C 0.8917(3) 0.80554(15) 0.18416(10) 0.0279(5) Uani 1 1 d . . . C23 C 0.5206(4) 0.74492(15) 0.20017(9) 0.0284(5) Uani 1 1 d . . . C26 C 0.9733(4) 0.78631(16) 0.24486(10) 0.0329(5) Uani 1 1 d . . . C16 C -0.2099(4) 0.47448(17) -0.06918(10) 0.0391(6) Uani 1 1 d . . . C34 C 0.4324(4) 0.97817(15) 0.23196(9) 0.0321(5) Uani 1 1 d . . . C12 C 0.0541(3) 0.59877(14) -0.08129(9) 0.0278(5) Uani 1 1 d . . . C14 C 0.1333(4) 0.44510(16) -0.11580(12) 0.0432(6) Uani 1 1 d . . . C17 C -0.1499(4) 0.56730(16) -0.06245(10) 0.0337(5) Uani 1 1 d . . . C25 C 0.8285(4) 0.74743(15) 0.28260(10) 0.0338(5) Uani 1 1 d . . . C15 C -0.0668(4) 0.41392(18) -0.09520(11) 0.0429(6) Uani 1 1 d . . . C13 C 0.1950(4) 0.53761(16) -0.10860(10) 0.0356(5) Uani 1 1 d . . . H37 H 0.822(3) 1.0894(15) 0.1327(10) 0.028(5) Uiso 1 1 d . . . H36 H 0.956(4) 1.0578(16) 0.2322(10) 0.039(6) Uiso 1 1 d . . . H13 H 0.334(4) 0.5605(16) -0.1239(10) 0.039(6) Uiso 1 1 d . . . H23 H 0.359(4) 0.7297(16) 0.1840(10) 0.040(6) Uiso 1 1 d . . . H33 H 0.191(3) 0.9832(16) 0.1557(10) 0.036(6) Uiso 1 1 d . . . H27 H 0.990(3) 0.8300(16) 0.1598(10) 0.035(6) Uiso 1 1 d . . . H25 H 0.887(3) 0.7356(15) 0.3242(11) 0.034(6) Uiso 1 1 d . . . H24 H 0.501(3) 0.6980(16) 0.2863(10) 0.034(6) Uiso 1 1 d . . . H26 H 1.138(4) 0.8004(16) 0.2602(10) 0.037(6) Uiso 1 1 d . . . H17 H -0.246(3) 0.6092(16) -0.0439(10) 0.035(6) Uiso 1 1 d . . . H34 H 0.329(4) 0.9497(16) 0.2563(10) 0.040(6) Uiso 1 1 d . . . H35 H 0.714(3) 0.9867(16) 0.2956(11) 0.040(6) Uiso 1 1 d . . . H16 H -0.347(4) 0.4576(17) -0.0540(11) 0.046(7) Uiso 1 1 d . . . H15 H -0.104(4) 0.3552(18) -0.0984(10) 0.041(7) Uiso 1 1 d . . . H14 H 0.231(4) 0.4028(19) -0.1362(12) 0.055(7) Uiso 1 1 d . . . H111 H 0.370(5) 0.771(2) -0.0731(13) 0.064(9) Uiso 1 1 d . . . H100 H -0.373(5) 0.854(3) 0.0253(15) 0.100(12) 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 0.0331(4) 0.0227(4) 0.0292(4) -0.0031(3) -0.0092(3) 0.0016(3) O31 0.0274(7) 0.0220(7) 0.0275(8) 0.0001(6) -0.0080(6) -0.0018(6) O21 0.0266(8) 0.0342(9) 0.0284(8) 0.0055(6) -0.0034(6) -0.0014(6) O200 0.0337(8) 0.0304(8) 0.0191(7) 0.0031(6) -0.0025(6) -0.0064(6) C32 0.0278(10) 0.0189(10) 0.0193(10) -0.0019(8) 0.0009(8) 0.0021(8) O12 0.0378(8) 0.0283(8) 0.0420(9) -0.0118(7) -0.0005(7) 0.0007(7) O100 0.0294(8) 0.0447(10) 0.0212(7) 0.0063(7) -0.0002(6) -0.0026(7) C31 0.0261(10) 0.0181(10) 0.0201(10) -0.0018(8) -0.0008(8) 0.0026(8) O11 0.0412(9) 0.0278(9) 0.0577(11) -0.0101(8) 0.0122(8) -0.0068(7) C22 0.0267(10) 0.0209(10) 0.0224(10) -0.0021(8) -0.0002(8) 0.0020(8) C37 0.0263(10) 0.0261(11) 0.0257(11) -0.0008(9) 0.0011(8) 0.0016(8) C33 0.0311(11) 0.0237(11) 0.0248(11) -0.0039(9) 0.0014(9) -0.0020(9) C36 0.0299(11) 0.0338(12) 0.0252(11) -0.0043(9) -0.0048(9) 0.0043(9) C21 0.0288(11) 0.0196(10) 0.0239(10) -0.0012(8) 0.0024(8) 0.0019(8) C35 0.0438(13) 0.0338(13) 0.0195(11) -0.0007(9) -0.0012(9) 0.0056(10) C24 0.0378(12) 0.0337(12) 0.0304(12) 0.0081(10) 0.0023(10) -0.0025(10) C11 0.0321(11) 0.0290(12) 0.0232(10) 0.0012(9) -0.0043(9) 0.0012(9) C27 0.0278(11) 0.0285(12) 0.0271(11) 0.0026(9) 0.0019(9) -0.0006(9) C23 0.0282(11) 0.0286(11) 0.0271(11) 0.0039(9) -0.0014(9) -0.0012(9) C26 0.0286(11) 0.0382(13) 0.0296(12) -0.0011(10) -0.0054(9) -0.0009(10) C16 0.0395(13) 0.0396(14) 0.0344(13) 0.0070(11) -0.0106(10) -0.0097(11) C34 0.0419(12) 0.0305(12) 0.0247(11) 0.0017(9) 0.0071(9) -0.0021(10) C12 0.0329(11) 0.0249(11) 0.0232(10) -0.0005(9) -0.0059(8) 0.0007(9) C14 0.0538(15) 0.0295(13) 0.0429(14) -0.0101(11) -0.0077(11) 0.0047(11) C17 0.0349(12) 0.0336(13) 0.0300(11) -0.0004(10) -0.0063(9) 0.0011(10) C25 0.0436(13) 0.0332(13) 0.0224(11) 0.0031(9) -0.0046(9) 0.0032(10) C15 0.0562(16) 0.0256(13) 0.0410(14) 0.0013(11) -0.0169(11) -0.0051(12) C13 0.0400(13) 0.0314(13) 0.0340(12) -0.0037(10) -0.0009(10) 0.0014(10) _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 O12 2.3375(16) . ? Na1 O31 2.3391(15) . ? Na1 O21 2.3482(15) . ? Na1 O31 2.3853(14) 3_575 ? Na1 O100 2.6637(16) . ? Na1 O200 2.6828(15) . ? Na1 Na1 3.5157(16) 3_575 ? O31 C31 1.244(2) . ? O31 Na1 2.3853(14) 3_575 ? O21 C21 1.221(2) . ? O200 C31 1.281(2) 3_675 ? C32 C33 1.392(3) . ? C32 C37 1.395(3) . ? C32 C31 1.504(3) . ? O12 C11 1.218(2) . ? O100 C21 1.317(2) 1_455 ? C31 O200 1.281(2) 3_675 ? O11 C11 1.321(2) . ? C22 C27 1.384(3) . ? C22 C23 1.391(3) . ? C22 C21 1.494(3) . ? C37 C36 1.387(3) . ? C33 C34 1.390(3) . ? C36 C35 1.386(3) . ? C21 O100 1.317(2) 1_655 ? C35 C34 1.370(3) . ? C24 C25 1.380(3) . ? C24 C23 1.385(3) . ? C11 C12 1.491(3) . ? C27 C26 1.394(3) . ? C26 C25 1.376(3) . ? C16 C15 1.382(4) . ? C16 C17 1.390(3) . ? C12 C17 1.383(3) . ? C12 C13 1.393(3) . ? C14 C15 1.378(4) . ? C14 C13 1.389(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 O12 Na1 O31 163.38(6) . . ? O12 Na1 O21 91.62(6) . . ? O31 Na1 O21 96.10(5) . . ? O12 Na1 O31 90.25(6) . 3_575 ? O31 Na1 O31 83.83(5) . 3_575 ? O21 Na1 O31 173.09(6) . 3_575 ? O12 Na1 O100 85.21(5) . . ? O31 Na1 O100 108.25(5) . . ? O21 Na1 O100 97.37(5) . . ? O31 Na1 O100 76.16(5) 3_575 . ? O12 Na1 O200 82.05(5) . . ? O31 Na1 O200 85.64(5) . . ? O21 Na1 O200 75.66(5) . . ? O31 Na1 O200 111.19(5) 3_575 . ? O100 Na1 O200 165.25(6) . . ? O12 Na1 Na1 129.83(5) . 3_575 ? O31 Na1 Na1 42.42(4) . 3_575 ? O21 Na1 Na1 138.10(5) . 3_575 ? O31 Na1 Na1 41.41(3) 3_575 3_575 ? O100 Na1 Na1 92.64(5) . 3_575 ? O200 Na1 Na1 101.23(4) . 3_575 ? C31 O31 Na1 133.02(12) . . ? C31 O31 Na1 126.16(12) . 3_575 ? Na1 O31 Na1 96.17(5) . 3_575 ? C21 O21 Na1 134.16(13) . . ? C31 O200 Na1 138.99(12) 3_675 . ? C33 C32 C37 118.97(18) . . ? C33 C32 C31 119.15(17) . . ? C37 C32 C31 121.84(17) . . ? C11 O12 Na1 133.14(13) . . ? C21 O100 Na1 164.75(13) 1_455 . ? O31 C31 O200 123.25(17) . 3_675 ? O31 C31 C32 119.63(17) . . ? O200 C31 C32 117.11(16) 3_675 . ? C27 C22 C23 119.56(18) . . ? C27 C22 C21 122.46(17) . . ? C23 C22 C21 117.91(16) . . ? C36 C37 C32 120.20(19) . . ? C34 C33 C32 120.30(19) . . ? C35 C36 C37 120.12(19) . . ? O21 C21 O100 122.71(17) . 1_655 ? O21 C21 C22 121.97(17) . . ? O100 C21 C22 115.31(16) 1_655 . ? C34 C35 C36 120.09(19) . . ? C25 C24 C23 119.8(2) . . ? O12 C11 O11 123.14(19) . . ? O12 C11 C12 123.22(18) . . ? O11 C11 C12 113.63(18) . . ? C22 C27 C26 119.80(19) . . ? C24 C23 C22 120.34(19) . . ? C25 C26 C27 120.17(19) . . ? C15 C16 C17 120.0(2) . . ? C35 C34 C33 120.3(2) . . ? C17 C12 C13 119.6(2) . . ? C17 C12 C11 119.31(19) . . ? C13 C12 C11 120.96(19) . . ? C15 C14 C13 119.6(2) . . ? C12 C17 C16 120.0(2) . . ? C26 C25 C24 120.3(2) . . ? C14 C15 C16 120.5(2) . . ? C14 C13 C12 120.2(2) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.08 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.245 _refine_diff_density_min -0.237 _refine_diff_density_rms 0.050 _database_code_depnum_ccdc_archive 'CCDC 918825'