# Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 2002 data_Na_C16H15O10_2(CH4O)__DRB234 _database_code_CSD 178772 _audit_creation_method 'RAELSPUB and manual entry' _journal_coden_Cambridge 440 _publ_requested_journal 'New Journal of Chemistry' loop_ _publ_author_name 'Bishop, Roger' 'Craig, Donald C.' 'Djaidi, Djamal' 'Scudder, Marcia L.' _publ_contact_author_name 'Prof Roger Bishop' _publ_contact_author_address ; Chemistry University of New South Wales UNSW Sydney N.S.W. 2052 AUSTRALIA ; _publ_contact_author_email 'R.BISHOP@UNSW.EDU.AU' _publ_section_title ; Schroeter and Vossen's red salt revealed ; _publ_section_references ; Altomare, A., Burla, M.C., Camalli, M., Cascarano, G., Giacovazzo, C., Guagliardi, A., Polidori, G., J. Appl. Cryst., 1994, 27, 435. Ibers, J.A. and Hamilton, W.C., (Eds) International Tables for X-Ray Crystallography Vol. 4 , Kynoch Press, Birmingham, 1974. Rae, A.D., RAELS. A comprehensive Constrained Least Squares Refinement Program, University of New South Wales, 1989. ; _publ_section_figure_captions ? _publ_section_exptl_prep ? _publ_section_exptl_refinement ; Reflection data were measured with an Enraf-Nonius CAD4 diffractometer using graphite monochromated molybdenum radiation. Data were corrected for decomposition but not for absorption. The structure was determined by direct phasing and Fourier methods, with hydrogen atoms included in calculated positions. Refinement of hon-hydrogen atoms was anisotropic. ; # CHEMICAL DATA _chemical_name_systematic ? _chemical_formula_moiety 'Na 1+,C16 H15 O10 1-,2(C H4 O)' _chemical_formula_sum 'C18 H23 Na O12' _chemical_formula_iupac ? _chemical_formula_weight 454.4 # CRYSTAL DATA _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 -x,-y,-z _cell_length_a 9.680(6) _cell_length_b 10.925(7) _cell_length_c 11.553(8) _cell_angle_alpha 66.78(3) _cell_angle_beta 73.38(3) _cell_angle_gamma 76.74(3) _cell_volume 1066(1) _cell_formula_units_Z 2 _cell_measurement_reflns_used 25 _cell_measurement_theta_min 15 _cell_measurement_theta_max 22 _cell_measurement_temperature 294 _exptl_crystal_description block _exptl_crystal_colour pink _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_size_rad ? _exptl_crystal_density_diffrn 1.41 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 476.0 _exptl_absorpt_coefficient_mu 0.128 _exptl_absorpt_correction_type none _exptl_absorpt_process_details ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? # EXPERIMENTAL DATA _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_device_type 'Nonius CAD-4' _diffrn_measurement_method \w--2\q _diffrn_reflns_number 2762 _diffrn_reflns_av_R_equivalents 0.018 _diffrn_reflns_theta_max 22 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 12 _diffrn_standards_number 1 _diffrn_standards_interval_time 30min _diffrn_standards_decay_% 36 # REFINEMENT DATA _refine_special_details ? _reflns_number_total 2601 _reflns_number_gt 1849 _reflns_threshold_expression I>3\s(I) _refine_ls_structure_factor_coef F _refine_ls_R_factor_gt 0.055 _refine_ls_wR_factor_ref 0.073 _refine_ls_hydrogen_treatment noref _refine_ls_number_reflns 1849 _refine_ls_number_parameters 280 _refine_ls_goodness_of_fit_ref 1.63 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[\s^2^(F) + 0.0016F^2^]' _refine_ls_shift/su_max 0.003 _refine_diff_density_max 0.38 _refine_diff_density_min -0.30 _refine_ls_extinction_method none _refine_ls_extinction_coef ? _atom_type_scat_source 'International Tables for X-ray Crystallography, Vol. IV' # ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_type_symbol _atom_site_occupancy O1 0.6089(4) 0.4729(3) 0.8786(3) 0.0552(9) Uani O ? O2 0.6948(4) 0.4334(3) 0.2916(3) 0.0587(9) Uani O ? O3 0.6031(4) 0.1804(3) 0.9558(3) 0.063(1) Uani O ? O4 0.7199(4) 0.1101(3) 0.7937(3) 0.0585(9) Uani O ? O5 0.7055(4) 0.7370(3) 0.7278(3) 0.0615(9) Uani O ? O6 0.8532(3) 0.7238(3) 0.5445(3) 0.0538(8) Uani O ? O7 0.9793(4) 0.5555(3) 0.2951(3) 0.069(1) Uani O ? O8 0.8353(3) 0.7481(3) 0.2493(3) 0.067(1) Uani O ? O9 0.6960(6) 0.1331(4) 0.4751(4) 0.112(2) Uani O ? O10 0.5255(4) 0.1730(3) 0.6319(4) 0.075(1) Uani O ? C1 0.6993(4) 0.3741(4) 0.6102(4) 0.035(1) Uani C ? C2 0.6668(4) 0.3392(4) 0.7437(4) 0.038(1) Uani C ? C3 0.6485(4) 0.4606(4) 0.7726(4) 0.040(1) Uani C ? C4 0.6744(4) 0.5798(4) 0.6432(4) 0.039(1) Uani C ? C5 0.7514(4) 0.5102(4) 0.5468(4) 0.035(1) Uani C ? C6 0.7311(4) 0.5616(4) 0.4083(4) 0.038(1) Uani C ? C7 0.7077(4) 0.4333(4) 0.3940(4) 0.040(1) Uani C ? C8 0.6877(4) 0.3279(4) 0.5183(4) 0.038(1) Uani C ? C9 0.6554(5) 0.2070(4) 0.8415(4) 0.045(1) Uani C ? C10 0.7142(7) -0.0273(5) 0.8816(5) 0.084(2) Uani C ? C11 0.7454(5) 0.6865(4) 0.6465(4) 0.044(1) Uani C ? C12 0.9303(6) 0.8266(5) 0.5387(6) 0.080(2) Uani C ? C13 0.8628(5) 0.6184(4) 0.3124(4) 0.041(1) Uani C ? C14 0.9581(7) 0.8138(6) 0.1597(6) 0.106(2) Uani C ? C15 0.6387(6) 0.2016(4) 0.5376(4) 0.048(1) Uani C ? C16 0.4701(6) 0.0481(5) 0.6621(7) 0.103(2) Uani C ? Na 0.4780(2) 0.3260(2) 1.0712(2) 0.0552(6) Uani Na ? O1Me1 0.2981(4) 0.3591(4) 0.9600(4) 0.083(1) Uani O ? C1Me1 0.1617(8) 0.4041(7) 1.0064(7) 0.105(2) Uani C ? O1Me2 0.6592(4) 0.2493(4) 1.1907(3) 0.077(1) Uani O ? C1Me2 0.7946(8) 0.1849(8) 1.1629(7) 0.108(2) Uani C ? HC4 0.5768 0.6228 0.6234 0.039 Uani H ? HC5 0.8580 0.4966 0.5432 0.035 Uani H ? HC6 0.6429 0.6303 0.3981 0.038 Uani H ? H1C10 0.7662 -0.0898 0.8342 0.084 Uani H ? H2C10 0.7620 -0.0432 0.9534 0.084 Uani H ? H3C10 0.6104 -0.0437 0.9181 0.084 Uani H ? H1C12 1.0089 0.8470 0.4584 0.080 Uani H ? H2C12 0.8607 0.9100 0.5378 0.080 Uani H ? H3C12 0.9744 0.7933 0.6159 0.080 Uani H ? H1C14 0.9250 0.9114 0.1175 0.106 Uani H ? H2C14 1.0338 0.8039 0.2075 0.106 Uani H ? H3C14 1.0003 0.7716 0.0924 0.106 Uani H ? H1C16 0.3835 0.0379 0.7358 0.103 Uani H ? H2C16 0.4412 0.0501 0.5848 0.103 Uani H ? H3C16 0.5475 -0.0295 0.6863 0.103 Uani H ? H1O1Me1 0.3006 0.4309 0.8730 0.083 Uani H ? H1C1Me1 0.1300 0.3460 1.0985 0.105 Uani H ? H2C1Me1 0.1564 0.4987 1.0008 0.105 Uani H ? H3C1Me1 0.0964 0.4013 0.9545 0.105 Uani H ? H1O1Me2 0.6718 0.3147 1.2265 0.077 Uani H ? H1C1Me2 0.7910 0.1170 1.1262 0.108 Uani H ? H2C1Me2 0.8600 0.2516 1.0984 0.108 Uani H ? H3C1Me2 0.8328 0.1386 1.2435 0.108 Uani H ? loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 _atom_site_aniso_type_symbol O1 0.095(2) 0.050(2) 0.029(2) -0.032(2) 0.000(2) -0.020(2) O O2 0.092(2) 0.064(2) 0.037(2) -0.025(2) -0.022(2) -0.021(2) O O3 0.109(3) 0.048(2) 0.034(2) -0.027(2) -0.007(2) -0.015(2) O O4 0.090(2) 0.036(2) 0.050(2) -0.015(2) -0.005(2) -0.019(2) O O5 0.101(3) 0.053(2) 0.042(2) -0.036(2) 0.000(2) -0.026(2) O O6 0.061(2) 0.048(2) 0.059(2) -0.025(2) 0.001(2) -0.027(2) O O7 0.054(2) 0.076(2) 0.063(2) -0.005(2) -0.001(2) -0.022(2) O O8 0.071(2) 0.054(2) 0.060(2) -0.023(2) -0.005(2) -0.002(2) O O9 0.195(5) 0.073(3) 0.073(3) -0.061(3) 0.031(3) -0.050(2) O O10 0.057(2) 0.051(2) 0.124(3) -0.022(2) 0.004(2) -0.046(2) O C1 0.037(2) 0.037(2) 0.036(3) -0.005(2) -0.009(2) -0.018(2) C C2 0.056(3) 0.033(2) 0.030(2) -0.016(2) -0.008(2) -0.012(2) C C3 0.052(3) 0.041(2) 0.033(3) -0.019(2) -0.005(2) -0.013(2) C C4 0.051(3) 0.039(2) 0.035(2) -0.017(2) -0.007(2) -0.016(2) C C5 0.046(2) 0.038(2) 0.028(2) -0.012(2) -0.005(2) -0.017(2) C C6 0.041(2) 0.043(2) 0.034(2) -0.013(2) -0.005(2) -0.016(2) C C7 0.046(3) 0.045(3) 0.035(3) -0.008(2) -0.010(2) -0.020(2) C C8 0.046(2) 0.041(2) 0.034(3) -0.012(2) -0.009(2) -0.018(2) C C9 0.059(3) 0.045(3) 0.040(3) -0.021(2) -0.009(2) -0.020(2) C C10 0.135(5) 0.037(3) 0.078(4) -0.017(3) -0.023(4) -0.016(3) C C11 0.061(3) 0.043(3) 0.030(3) -0.017(2) -0.009(2) -0.011(2) C C12 0.076(4) 0.071(3) 0.105(5) -0.045(3) 0.012(3) -0.045(3) C C13 0.053(3) 0.047(3) 0.030(3) -0.011(2) -0.015(2) -0.013(2) C C14 0.098(5) 0.086(4) 0.093(5) -0.047(4) 0.011(4) 0.006(4) C C15 0.076(3) 0.040(3) 0.035(3) -0.009(2) -0.017(3) -0.016(2) C C16 0.085(4) 0.056(3) 0.178(7) -0.035(3) -0.016(4) -0.047(4) C Na 0.089(1) 0.051(1) 0.035(1) -0.0268(9) -0.0053(9) -0.0207(8) Na O1Me1 0.090(3) 0.095(3) 0.062(3) -0.019(2) -0.023(2) -0.018(2) O C1Me1 0.102(5) 0.123(6) 0.086(5) -0.010(4) -0.033(4) -0.027(4) C O1Me2 0.094(3) 0.090(3) 0.071(2) -0.012(2) -0.027(2) -0.047(2) O C1Me2 0.089(5) 0.152(7) 0.118(6) -0.024(4) 0.000(4) -0.094(5) C # MOLECULAR GEOMETRY loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C3 1.226(5) 1_555 1_555 no O1 Na 2.374(3) 1_555 1_555 no O1 Na 2.397(3) 1_555 2_667 no O2 C7 1.224(5) 1_555 1_555 no O3 C9 1.211(5) 1_555 1_555 no O3 Na 2.375(3) 1_555 1_555 no O4 C9 1.333(5) 1_555 1_555 no O4 C10 1.445(5) 1_555 1_555 no O5 C11 1.199(5) 1_555 1_555 no O5 Na 2.441(3) 1_555 2_667 no O6 C11 1.325(5) 1_555 1_555 no O6 C12 1.455(5) 1_555 1_555 no O7 C13 1.187(5) 1_555 1_555 no O8 C13 1.316(5) 1_555 1_555 no O8 C14 1.449(6) 1_555 1_555 no O9 C15 1.182(5) 1_555 1_555 no O10 C15 1.301(5) 1_555 1_555 no O10 C16 1.457(6) 1_555 1_555 no C1 C2 1.391(5) 1_555 1_555 no C1 C5 1.508(5) 1_555 1_555 no C1 C8 1.383(5) 1_555 1_555 no C2 C3 1.452(5) 1_555 1_555 no C2 C9 1.446(5) 1_555 1_555 no C3 C4 1.547(6) 1_555 1_555 no C4 C5 1.519(5) 1_555 1_555 no C4 C11 1.500(6) 1_555 1_555 no C5 C6 1.527(5) 1_555 1_555 no C6 C7 1.548(6) 1_555 1_555 no C6 C13 1.500(5) 1_555 1_555 no C7 C8 1.437(6) 1_555 1_555 no C8 C15 1.474(6) 1_555 1_555 no Na O1 2.374(3) 1_555 1_555 no Na O1 2.397(3) 1_555 2_667 no Na O3 2.375(3) 1_555 1_555 no Na O5 2.441(3) 1_555 2_667 no Na O1Me1 2.332(4) 1_555 1_555 no Na O1Me2 2.342(4) 1_555 1_555 no O1Me1 C1Me1 1.333(7) 1_555 1_555 no O1Me2 C1Me2 1.353(7) 1_555 1_555 no 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C3 O1 Na 127.0(2) 1_555 1_555 1_555 no C3 O1 Na 128.8(3) 1_555 1_555 2_667 no Na O1 Na 96.9(1) 1_555 1_555 2_667 no C9 O3 Na 129.6(3) 1_555 1_555 1_555 no C9 O4 C10 117.3(4) 1_555 1_555 1_555 no C11 O5 Na 128.9(3) 1_555 1_555 2_667 no C11 O6 C12 116.2(3) 1_555 1_555 1_555 no C13 O8 C14 116.3(4) 1_555 1_555 1_555 no C15 O10 C16 117.3(4) 1_555 1_555 1_555 no C2 C1 C5 109.6(3) 1_555 1_555 1_555 no C2 C1 C8 139.6(4) 1_555 1_555 1_555 no C5 C1 C8 110.6(3) 1_555 1_555 1_555 no C1 C2 C3 108.3(3) 1_555 1_555 1_555 no C1 C2 C9 128.2(3) 1_555 1_555 1_555 no C3 C2 C9 123.6(3) 1_555 1_555 1_555 no O1 C3 C2 127.9(4) 1_555 1_555 1_555 no O1 C3 C4 123.9(4) 1_555 1_555 1_555 no C2 C3 C4 108.0(3) 1_555 1_555 1_555 no C3 C4 C5 102.8(3) 1_555 1_555 1_555 no C3 C4 C11 114.1(3) 1_555 1_555 1_555 no C5 C4 C11 118.1(3) 1_555 1_555 1_555 no C1 C5 C4 103.2(3) 1_555 1_555 1_555 no C1 C5 C6 105.6(3) 1_555 1_555 1_555 no C4 C5 C6 123.9(3) 1_555 1_555 1_555 no C5 C6 C7 102.6(3) 1_555 1_555 1_555 no C5 C6 C13 111.8(3) 1_555 1_555 1_555 no C7 C6 C13 111.0(3) 1_555 1_555 1_555 no O2 C7 C6 121.8(4) 1_555 1_555 1_555 no O2 C7 C8 128.4(4) 1_555 1_555 1_555 no C6 C7 C8 109.4(3) 1_555 1_555 1_555 no C1 C8 C7 109.4(3) 1_555 1_555 1_555 no C1 C8 C15 128.7(4) 1_555 1_555 1_555 no C7 C8 C15 121.2(3) 1_555 1_555 1_555 no O3 C9 O4 120.9(4) 1_555 1_555 1_555 no O3 C9 C2 127.1(4) 1_555 1_555 1_555 no O4 C9 C2 111.9(4) 1_555 1_555 1_555 no O5 C11 O6 123.8(4) 1_555 1_555 1_555 no O5 C11 C4 124.4(4) 1_555 1_555 1_555 no O6 C11 C4 111.7(4) 1_555 1_555 1_555 no O7 C13 O8 123.1(4) 1_555 1_555 1_555 no O7 C13 C6 124.7(4) 1_555 1_555 1_555 no O8 C13 C6 112.2(4) 1_555 1_555 1_555 no O9 C15 O10 123.3(4) 1_555 1_555 1_555 no O9 C15 C8 124.1(4) 1_555 1_555 1_555 no O10 C15 C8 112.6(4) 1_555 1_555 1_555 no O1 Na O1 83.1(1) 1_555 1_555 2_667 no O1 Na O3 77.4(1) 1_555 1_555 1_555 no O1 Na O5 156.9(1) 1_555 1_555 2_667 no O1 Na O1Me1 87.8(1) 1_555 1_555 1_555 no O1 Na O1Me2 98.3(1) 1_555 1_555 1_555 no O1 Na O3 160.5(1) 2_667 1_555 1_555 no O1 Na O5 74.4(1) 2_667 1_555 2_667 no O1 Na O1Me1 94.5(1) 2_667 1_555 1_555 no O1 Na O1Me2 95.2(1) 2_667 1_555 1_555 no O3 Na O5 124.8(1) 1_555 1_555 2_667 no O3 Na O1Me1 83.8(1) 1_555 1_555 1_555 no O3 Na O1Me2 88.7(1) 1_555 1_555 1_555 no O5 Na O1Me1 88.3(1) 2_667 1_555 1_555 no O5 Na O1Me2 89.5(1) 2_667 1_555 1_555 no O1Me1 Na O1Me2 169.1(2) 1_555 1_555 1_555 no Na O1Me1 C1Me1 119.5(4) 1_555 1_555 1_555 no Na O1Me2 C1Me2 128.9(4) 1_555 1_555 1_555 no