# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2012 data_publication_text _journal_name_full CrystEngComm #TrackingRef '- KO_rev.CIF' _journal_coden_Cambridge 1350 _publ_contact_author_name 'Prof.Dr.Josef Breu' _publ_contact_author_address ;Anorganische Chemie I Universit\"atsstr. 30 95447 Bayreuth ; _publ_contact_author_email josef.breu@uni-bayreuth.de _publ_contact_author_phone '++49 921 552530' _publ_section_title ; Polymorphism in co-crystals: A metastable form of the ionic co-crystal 2 HBz?1 NaBz crystallised by flash evaporation ; loop_ _publ_author_name _publ_author_address C.Butterhof ;Anorganische Chemie I Universit\"at Bayreuth Universit\"atsstr. 30 95447 Bayreuth ; K.Barwinkel ;Anorganische Chemie III Universit\"at Bayreuth Universit\"atsstr. 30 95447 Bayreuth ; J.Senker ;Anorganische Chemie III Universit\"at Bayreuth Universit\"atsstr. 30 95447 Bayreuth ; J.Breu ;Anorganische Chemie I Universit\"at Bayreuth Universit\"atsstr. 30 95447 Bayreuth ; data_ko _database_code_depnum_ccdc_archive 'CCDC 875039' #TrackingRef '- KO_rev.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.8912(14) _cell_length_b 12.082(2) _cell_length_c 13.372(3) _cell_angle_alpha 109.97(3) _cell_angle_beta 100.51(3) _cell_angle_gamma 103.88(3) _cell_volume 972.3(3) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 1652 _cell_measurement_theta_min 1.90 _cell_measurement_theta_max 26.14 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.212 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.326 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 404 _exptl_absorpt_coefficient_mu 0.116 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; As mentioned in the experimental section, flash evaporation only yields comparatively small crystals showing relatively low diffraction power. Moreover, the metastable form transforms into the stable form. At room temperature, the single crystal is completely deteriorated within 24 h hours when only powder rings remained. Even at low temperature (-100\%C) where the final data set was collected, the crystals are not infinitely stable. Moreover, the low triclinic symmetry required to measure more than 180 \% in ?. We ended up measuring 220 \% but nevertheless the orientation of the crystal by chance was suboptimal and only gave a completeness of 92.3 %. Needless to say that further rotation or re-measuring after re-orientation was not possible because of the instability. In that line the total measurement time also necessarily represented a compromise. We feel that we actually achieved the best signal to noise ratio possible given the instability that limited the total data collection time. Neverthe-less this best data set remained weak and as consequence the GOOF deviates from 1. Nevertheless, crystal structure solution and refinement turned out to be straightforward de-spite the low intensity data. ; _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 'STOE IPDS I' _diffrn_measurement_method 'phi scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8497 _diffrn_reflns_av_R_equivalents 0.0896 _diffrn_reflns_av_sigmaI/netI 0.1438 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.90 _diffrn_reflns_theta_max 26.14 _reflns_number_total 3576 _reflns_number_gt 1209 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'STOE IPDS I' _computing_cell_refinement 'STOE IPDS I' _computing_data_reduction 'STOE X-RED' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Diamond Version 3.0e' _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^)+(0.0374P)^2^+0.0000P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3576 _refine_ls_number_parameters 258 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1643 _refine_ls_R_factor_gt 0.0461 _refine_ls_wR_factor_ref 0.1309 _refine_ls_wR_factor_gt 0.0920 _refine_ls_goodness_of_fit_ref 0.765 _refine_ls_restrained_S_all 0.765 _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 Na2 Na 0.0000 0.0000 0.0000 0.0529(6) Uani 1 2 d S . . O3 O 0.0001(5) 0.1049(3) 0.1824(2) 0.0596(8) Uani 1 1 d . . . O1 O 0.2793(4) -0.0552(3) 0.1068(2) 0.0564(8) Uani 1 1 d . . . O2 O 0.2697(5) 0.0355(3) 0.2813(2) 0.0673(9) Uani 1 1 d . . . H2 H 0.1881 0.0623 0.2516 0.11(2) Uiso 1 1 calc R . . O6 O 0.2962(4) 0.1774(3) 0.0482(2) 0.0579(8) Uani 1 1 d . . . O5 O 0.5362(5) 0.3217(3) 0.2033(2) 0.0708(9) Uani 1 1 d . . . H5B H 0.5907 0.2670 0.1931 0.13(3) Uiso 1 1 calc R . . C2 C 0.5020(7) -0.0779(4) 0.2532(4) 0.0554(11) Uani 1 1 d . . . C9 C -0.0372(7) 0.2482(4) 0.3463(3) 0.0494(11) Uani 1 1 d . . . C14 C -0.1787(7) 0.2706(4) 0.4062(3) 0.0585(12) Uani 1 1 d . . . H14A H -0.3213 0.2324 0.3710 0.070 Uiso 1 1 calc R . . C8 C -0.1144(7) 0.1633(4) 0.2258(3) 0.0522(11) Uani 1 1 d . . . C16 C 0.2505(7) 0.3754(4) 0.1346(3) 0.0539(11) Uani 1 1 d . . . C10 C 0.1735(7) 0.3087(4) 0.3997(3) 0.0576(12) Uani 1 1 d . . . H10A H 0.2700 0.2952 0.3605 0.069 Uiso 1 1 calc R . . C1 C 0.3413(7) -0.0321(4) 0.2063(4) 0.0540(11) Uani 1 1 d . . . C15 C 0.3605(7) 0.2817(4) 0.1242(4) 0.0527(11) Uani 1 1 d . . . C12 C 0.1033(8) 0.4101(5) 0.5704(4) 0.0652(13) Uani 1 1 d . . . H12A H 0.1505 0.4643 0.6451 0.078 Uiso 1 1 calc R . . C11 C 0.2426(8) 0.3892(5) 0.5111(4) 0.0679(13) Uani 1 1 d . . . H11A H 0.3850 0.4294 0.5458 0.082 Uiso 1 1 calc R . . C17 C 0.3523(8) 0.4998(5) 0.2049(4) 0.0676(13) Uani 1 1 d . . . H17A H 0.4924 0.5262 0.2446 0.081 Uiso 1 1 calc R . . C7 C 0.5655(8) -0.0513(5) 0.3648(4) 0.0783(16) Uani 1 1 d . . . H7A H 0.5062 -0.0041 0.4130 0.094 Uiso 1 1 calc R . . C13 C -0.1084(8) 0.3498(4) 0.5183(4) 0.0638(13) Uani 1 1 d . . . H13A H -0.2038 0.3623 0.5585 0.077 Uiso 1 1 calc R . . C21 C 0.0401(7) 0.3363(5) 0.0757(4) 0.0654(13) Uani 1 1 d . . . H21A H -0.0288 0.2531 0.0279 0.078 Uiso 1 1 calc R . . C3 C 0.5938(8) -0.1469(5) 0.1835(4) 0.0735(15) Uani 1 1 d . . . H3A H 0.5508 -0.1669 0.1076 0.088 Uiso 1 1 calc R . . C20 C -0.0660(8) 0.4225(6) 0.0892(5) 0.0757(14) Uani 1 1 d . . . H20A H -0.2069 0.3967 0.0513 0.091 Uiso 1 1 calc R . . C4 C 0.7501(9) -0.1864(6) 0.2264(5) 0.0911(19) Uani 1 1 d . . . H4A H 0.8147 -0.2305 0.1793 0.109 Uiso 1 1 calc R . . C19 C 0.0375(10) 0.5458(6) 0.1586(5) 0.0812(16) Uani 1 1 d . . . H19A H -0.0336 0.6032 0.1667 0.097 Uiso 1 1 calc R . . C18 C 0.2446(9) 0.5845(5) 0.2160(4) 0.0751(14) Uani 1 1 d . . . H18A H 0.3132 0.6681 0.2625 0.090 Uiso 1 1 calc R . . C6 C 0.7177(10) -0.0944(6) 0.4057(5) 0.0962(19) Uani 1 1 d . . . H6A H 0.7575 -0.0776 0.4810 0.115 Uiso 1 1 calc R . . C5 C 0.8096(9) -0.1614(6) 0.3365(6) 0.0933(18) Uani 1 1 d . . . H5A H 0.9123 -0.1897 0.3645 0.112 Uiso 1 1 calc R . . Na1 Na 0.5000 0.0000 0.0000 0.0635(7) Uani 1 2 d S . . O4 O -0.2938(5) 0.1510(3) 0.1685(2) 0.0598(8) Uani 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 Na2 0.0470(14) 0.0556(15) 0.0516(13) 0.0177(12) 0.0094(11) 0.0187(11) O3 0.059(2) 0.063(2) 0.0533(17) 0.0143(16) 0.0141(15) 0.0283(17) O1 0.056(2) 0.059(2) 0.0519(17) 0.0214(15) 0.0127(14) 0.0192(15) O2 0.072(2) 0.081(2) 0.0582(18) 0.0275(18) 0.0185(17) 0.042(2) O6 0.0518(19) 0.053(2) 0.0577(18) 0.0154(16) 0.0103(14) 0.0127(15) O5 0.057(2) 0.062(2) 0.068(2) 0.0064(17) -0.0061(17) 0.0213(18) C2 0.058(3) 0.059(3) 0.058(3) 0.027(2) 0.019(2) 0.027(2) C9 0.047(3) 0.051(3) 0.045(2) 0.017(2) 0.010(2) 0.015(2) C14 0.056(3) 0.063(3) 0.052(2) 0.018(2) 0.009(2) 0.023(2) C8 0.055(3) 0.053(3) 0.047(2) 0.020(2) 0.013(2) 0.017(2) C16 0.054(3) 0.051(3) 0.056(3) 0.023(2) 0.016(2) 0.015(2) C10 0.053(3) 0.059(3) 0.052(3) 0.018(2) 0.008(2) 0.015(2) C1 0.058(3) 0.052(3) 0.051(3) 0.016(2) 0.019(2) 0.020(2) C15 0.052(3) 0.050(3) 0.050(2) 0.017(2) 0.012(2) 0.013(2) C12 0.080(4) 0.059(3) 0.051(3) 0.017(2) 0.014(3) 0.023(3) C11 0.064(3) 0.071(4) 0.049(3) 0.015(2) 0.000(2) 0.015(3) C17 0.069(3) 0.065(3) 0.065(3) 0.023(3) 0.014(3) 0.024(3) C7 0.079(4) 0.094(4) 0.070(3) 0.036(3) 0.013(3) 0.046(3) C13 0.068(4) 0.068(3) 0.058(3) 0.024(3) 0.019(3) 0.028(3) C21 0.054(3) 0.065(3) 0.070(3) 0.025(3) 0.010(3) 0.018(3) C3 0.076(4) 0.086(4) 0.086(3) 0.046(3) 0.036(3) 0.048(3) C20 0.064(4) 0.083(4) 0.096(4) 0.048(4) 0.022(3) 0.034(3) C4 0.089(5) 0.108(5) 0.128(5) 0.075(4) 0.053(4) 0.065(4) C19 0.099(5) 0.083(4) 0.090(4) 0.046(4) 0.040(4) 0.052(4) C18 0.090(4) 0.064(4) 0.075(3) 0.028(3) 0.024(3) 0.030(3) C6 0.103(5) 0.110(5) 0.088(4) 0.054(4) 0.010(4) 0.051(4) C5 0.080(4) 0.097(5) 0.126(5) 0.062(4) 0.022(4) 0.051(4) Na1 0.0523(16) 0.0685(18) 0.0541(14) 0.0157(13) 0.0109(12) 0.0096(13) O4 0.052(2) 0.063(2) 0.0545(17) 0.0159(16) 0.0059(15) 0.0213(15) _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_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag Na1 O1 2.399(3) . . yes Na1 O4 2.281(3) . 1_655 yes Na1 O4 2.281(3) . 2_555 yes Na1 O1 2.399(3) . 2_655 yes Na2 O1 2.540(3) . . yes Na2 O3 2.333(3) . . yes Na2 O6 2.378(3) . . yes Na2 O1 2.540(3) . 2_555 yes Na2 O3 2.333(3) . 2_555 yes Na2 O6 2.378(3) . 2_555 yes O1 C1 1.230(5) . . yes O2 C1 1.316(6) . . yes O3 C8 1.270(6) . . yes O4 C8 1.275(6) . . yes O5 C15 1.312(6) . . yes O6 C15 1.229(6) . . yes O2 H2 0.8200 . . no O5 H5B 0.8200 . . no C1 C2 1.484(7) . . no C2 C7 1.374(7) . . no C2 C3 1.379(7) . . no C3 C4 1.388(9) . . no C4 C5 1.358(9) . . no C5 C6 1.364(10) . . no C6 C7 1.385(9) . . no C8 C9 1.493(5) . . no C9 C14 1.389(7) . . no C9 C10 1.382(7) . . no C10 C11 1.386(6) . . no C11 C12 1.368(8) . . no C12 C13 1.385(8) . . no C13 C14 1.389(6) . . no C15 C16 1.489(7) . . no C16 C21 1.395(7) . . no C16 C17 1.387(7) . . no C17 C18 1.386(9) . . no C18 C19 1.371(9) . . no C19 C20 1.376(10) . . no C20 C21 1.392(9) . . no C3 H3A 0.9300 . . no C4 H4A 0.9300 . . no C5 H5A 0.9300 . . no C6 H6A 0.9300 . . no C7 H7A 0.9300 . . no C10 H10A 0.9300 . . no C11 H11A 0.9300 . . no C12 H12A 0.9300 . . no C13 H13A 0.9300 . . no C14 H14A 0.9300 . . no C17 H17A 0.9300 . . no C18 H18A 0.9300 . . no C19 H19A 0.9300 . . no C20 H20A 0.9300 . . no C21 H21A 0.9300 . . 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 O1 Na1 O4 83.59(11) . . 1_655 yes O1 Na1 O4 96.41(11) . . 2_555 yes O1 Na1 O1 180.00 . . 2_655 yes O4 Na1 O4 180.00 1_655 . 2_555 yes O1 Na1 O4 96.41(11) 2_655 . 1_655 yes O1 Na1 O4 83.59(11) 2_655 . 2_555 yes O1 Na2 O3 78.96(11) . . . yes O1 Na2 O6 79.51(11) . . . yes O1 Na2 O1 180.00 . . 2_555 yes O1 Na2 O3 101.04(11) . . 2_555 yes O1 Na2 O6 100.49(11) . . 2_555 yes O3 Na2 O6 82.79(11) . . . yes O1 Na2 O3 101.04(11) 2_555 . . yes O3 Na2 O3 180.00 . . 2_555 yes O3 Na2 O6 97.21(11) . . 2_555 yes O1 Na2 O6 100.49(11) 2_555 . . yes O3 Na2 O6 97.21(11) 2_555 . . yes O6 Na2 O6 180.00 . . 2_555 yes O1 Na2 O3 78.96(11) 2_555 . 2_555 yes O1 Na2 O6 79.51(11) 2_555 . 2_555 yes O3 Na2 O6 82.79(11) 2_555 . 2_555 yes Na1 O1 Na2 88.43(10) . . . yes Na1 O1 C1 124.2(3) . . . yes Na2 O1 C1 131.4(3) . . . yes Na2 O3 C8 134.1(3) . . . yes Na1 O4 C8 129.9(3) 1_455 . . yes Na2 O6 C15 132.2(3) . . . yes C1 O2 H2 109.00 . . . no C15 O5 H5B 109.00 . . . no O1 C1 C2 123.6(4) . . . yes O1 C1 O2 122.8(4) . . . yes O2 C1 C2 113.7(4) . . . yes C3 C2 C7 118.8(5) . . . no C1 C2 C3 119.3(4) . . . no C1 C2 C7 121.9(5) . . . no C2 C3 C4 120.1(5) . . . no C3 C4 C5 120.6(6) . . . no C4 C5 C6 119.5(6) . . . no C5 C6 C7 120.7(6) . . . no C2 C7 C6 120.2(5) . . . no O4 C8 C9 119.4(4) . . . yes O3 C8 O4 121.3(3) . . . yes O3 C8 C9 119.3(4) . . . yes C8 C9 C10 121.4(4) . . . no C8 C9 C14 119.9(4) . . . no C10 C9 C14 118.7(4) . . . no C9 C10 C11 120.7(4) . . . no C10 C11 C12 120.6(5) . . . no C11 C12 C13 119.4(5) . . . no C12 C13 C14 120.2(5) . . . no C9 C14 C13 120.4(4) . . . no O5 C15 O6 122.7(5) . . . yes O5 C15 C16 113.6(4) . . . yes O6 C15 C16 123.8(4) . . . yes C15 C16 C17 120.9(4) . . . no C17 C16 C21 119.8(5) . . . no C15 C16 C21 119.3(4) . . . no C16 C17 C18 119.8(5) . . . no C17 C18 C19 120.4(6) . . . no C18 C19 C20 120.5(6) . . . no C19 C20 C21 120.1(6) . . . no C16 C21 C20 119.5(5) . . . no C2 C3 H3A 120.00 . . . no C4 C3 H3A 120.00 . . . no C3 C4 H4A 120.00 . . . no C5 C4 H4A 120.00 . . . no C4 C5 H5A 120.00 . . . no C6 C5 H5A 120.00 . . . no C5 C6 H6A 120.00 . . . no C7 C6 H6A 120.00 . . . no C2 C7 H7A 120.00 . . . no C6 C7 H7A 120.00 . . . no C9 C10 H10A 120.00 . . . no C11 C10 H10A 120.00 . . . no C10 C11 H11A 120.00 . . . no C12 C11 H11A 120.00 . . . no C11 C12 H12A 120.00 . . . no C13 C12 H12A 120.00 . . . no C12 C13 H13A 120.00 . . . no C14 C13 H13A 120.00 . . . no C9 C14 H14A 120.00 . . . no C13 C14 H14A 120.00 . . . no C16 C17 H17A 120.00 . . . no C18 C17 H17A 120.00 . . . no C17 C18 H18A 120.00 . . . no C19 C18 H18A 120.00 . . . no C18 C19 H19A 120.00 . . . no C20 C19 H19A 120.00 . . . no C19 C20 H20A 120.00 . . . no C21 C20 H20A 120.00 . . . no C16 C21 H21A 120.00 . . . no C20 C21 H21A 120.00 . . . no loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O2 H2 O3 0.82 1.73 2.551(4) 174.7 . O5 H5B O4 0.82 1.74 2.558(5) 178.7 1_655 _diffrn_measured_fraction_theta_max 0.923 _diffrn_reflns_theta_full 26.14 _diffrn_measured_fraction_theta_full 0.923 _refine_diff_density_max 0.235 _refine_diff_density_min -0.160 _refine_diff_density_rms 0.050 # Attachment '- TTFA_rev.CIF' data_ttfa _database_code_depnum_ccdc_archive 'CCDC 875040' #TrackingRef '- TTFA_rev.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _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 P2(1)/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 5.8402(12) _cell_length_b 14.499(3) _cell_length_c 22.136(4) _cell_angle_alpha 90.00 _cell_angle_beta 97.18(3) _cell_angle_gamma 90.00 _cell_volume 1859.7(6) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 8000 _cell_measurement_theta_min 1.85 _cell_measurement_theta_max 26.03 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.41 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.387 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 808 _exptl_absorpt_coefficient_mu 0.121 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; A 1-circle diffractometer was used for measurement (IPDS I). With this, full completeness is hardly achievable for low symmetry crystal systems. For measurement we could only use a 1-circle diffractometer. With this full completness is hardly achievable in low symmetry crystal systems. ; _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 'STOE IPDS I' _diffrn_measurement_method 'phi scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16321 _diffrn_reflns_av_R_equivalents 0.1090 _diffrn_reflns_av_sigmaI/netI 0.0674 _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 -27 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 1.85 _diffrn_reflns_theta_max 26.03 _reflns_number_total 3466 _reflns_number_gt 2140 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'STOE IPDS I' _computing_cell_refinement 'STOE IPDS I' _computing_data_reduction 'STOE X-RED' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Diamnond Version 3.0e' _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^)+(0.0650P)^2^+0.0000P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3466 _refine_ls_number_parameters 255 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0723 _refine_ls_R_factor_gt 0.0411 _refine_ls_wR_factor_ref 0.1173 _refine_ls_wR_factor_gt 0.0983 _refine_ls_goodness_of_fit_ref 0.949 _refine_ls_restrained_S_all 0.949 _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 0.41023(15) 0.61510(5) 0.48680(3) 0.0402(3) Uani 1 1 d . . . O4 O 0.0209(3) 0.61894(9) 0.54048(5) 0.0384(4) Uani 1 1 d . . . O1 O 0.1456(3) 0.69739(9) 0.41829(6) 0.0414(4) Uani 1 1 d . . . C9 C -0.0048(4) 0.53997(11) 0.63412(8) 0.0315(5) Uani 1 1 d . . . C8 C -0.0996(4) 0.56395(12) 0.56936(8) 0.0320(5) Uani 1 1 d . . . O5 O 0.4943(3) 0.74670(9) 0.54677(6) 0.0473(4) Uani 1 1 d . . . O6 O 0.1654(3) 0.78412(10) 0.58350(7) 0.0530(5) Uani 1 1 d . . . H6A H 0.1292 0.7316 0.5725 0.079(9) Uiso 1 1 calc R . . C2 C -0.1642(4) 0.71441(12) 0.33799(8) 0.0330(5) Uani 1 1 d . . . C14 C -0.1478(4) 0.49757(12) 0.67135(8) 0.0370(5) Uani 1 1 d . . . H14 H -0.2983 0.4822 0.6558 0.044 Uiso 1 1 calc R . . C10 C 0.2223(4) 0.56152(13) 0.65766(8) 0.0366(5) Uani 1 1 d . . . H10 H 0.3201 0.5892 0.6330 0.044 Uiso 1 1 calc R . . C11 C 0.3015(4) 0.54130(14) 0.71827(8) 0.0400(6) Uani 1 1 d . . . H11 H 0.4523 0.5558 0.7340 0.048 Uiso 1 1 calc R . . C7 C -0.0218(4) 0.75491(13) 0.29993(8) 0.0388(5) Uani 1 1 d . . . H7 H 0.1299 0.7693 0.3150 0.047 Uiso 1 1 calc R . . C12 C 0.1563(4) 0.49976(13) 0.75508(8) 0.0425(6) Uani 1 1 d . . . H12 H 0.2097 0.4866 0.7955 0.051 Uiso 1 1 calc R . . C6 C -0.1031(4) 0.77417(14) 0.23957(9) 0.0446(6) Uani 1 1 d . . . H6 H -0.0069 0.8014 0.2142 0.053 Uiso 1 1 calc R . . C20 C 0.7093(5) 1.02548(15) 0.56913(9) 0.0486(6) Uani 1 1 d . . . H20 H 0.8455 1.0466 0.5562 0.058 Uiso 1 1 calc R . . C3 C -0.3920(4) 0.69416(13) 0.31584(8) 0.0380(5) Uani 1 1 d . . . H3 H -0.4896 0.6680 0.3412 0.046 Uiso 1 1 calc R . . C1 C -0.0605(4) 0.68994(12) 0.40132(8) 0.0346(5) Uani 1 1 d . . . C15 C 0.3737(4) 0.80356(14) 0.56864(9) 0.0404(6) Uani 1 1 d . . . C13 C -0.0676(4) 0.47793(13) 0.73185(8) 0.0419(6) Uani 1 1 d . . . H13 H -0.1649 0.4501 0.7566 0.050 Uiso 1 1 calc R . . C4 C -0.4727(4) 0.71343(14) 0.25517(9) 0.0432(6) Uani 1 1 d . . . H4 H -0.6247 0.6998 0.2400 0.052 Uiso 1 1 calc R . . C18 C 0.3678(5) 1.05439(14) 0.61574(10) 0.0533(7) Uani 1 1 d . . . H18 H 0.2752 1.0949 0.6345 0.064 Uiso 1 1 calc R . . C16 C 0.4457(4) 0.90117(13) 0.58137(8) 0.0368(5) Uani 1 1 d . . . C5 C -0.3282(4) 0.75253(13) 0.21762(9) 0.0434(6) Uani 1 1 d . . . H5 H -0.3830 0.7644 0.1771 0.052 Uiso 1 1 calc R . . C21 C 0.6492(4) 0.93278(14) 0.56236(9) 0.0440(6) Uani 1 1 d . . . H21 H 0.7455 0.8920 0.5451 0.053 Uiso 1 1 calc R . . C17 C 0.3048(4) 0.96200(14) 0.60871(9) 0.0444(6) Uani 1 1 d . . . H17 H 0.1695 0.9410 0.6222 0.053 Uiso 1 1 calc R . . C19 C 0.5673(5) 1.08629(15) 0.59501(10) 0.0516(7) Uani 1 1 d . . . H19 H 0.6058 1.1485 0.5985 0.062 Uiso 1 1 calc R . . O3 O -0.2901(3) 0.53210(8) 0.54724(5) 0.0369(4) Uani 1 1 d . . . O2 O -0.2092(3) 0.65849(10) 0.43708(6) 0.0431(4) Uani 1 1 d . . . H2 H -0.1406 0.6465 0.4708 0.098(11) Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Na1 0.0454(7) 0.0315(4) 0.0400(4) -0.0029(3) -0.0089(4) 0.0019(3) O4 0.0433(11) 0.0385(7) 0.0318(6) 0.0030(5) -0.0013(6) -0.0066(7) O1 0.0377(11) 0.0448(8) 0.0393(7) 0.0063(6) -0.0055(7) -0.0024(7) C9 0.0358(15) 0.0267(9) 0.0312(9) -0.0021(7) 0.0018(9) -0.0008(8) C8 0.0390(15) 0.0257(9) 0.0304(9) -0.0018(7) 0.0011(9) 0.0021(9) O5 0.0499(12) 0.0367(8) 0.0536(8) -0.0126(6) 0.0002(7) 0.0023(7) O6 0.0516(13) 0.0377(8) 0.0708(10) -0.0111(7) 0.0128(9) -0.0069(8) C2 0.0377(15) 0.0279(9) 0.0323(9) 0.0001(7) 0.0002(9) 0.0010(9) C14 0.0403(15) 0.0313(10) 0.0385(10) -0.0017(8) 0.0015(9) -0.0029(9) C10 0.0388(15) 0.0358(10) 0.0348(9) -0.0016(8) 0.0026(9) -0.0018(9) C11 0.0387(16) 0.0433(11) 0.0355(10) -0.0026(8) -0.0055(9) 0.0028(10) C7 0.0378(16) 0.0375(10) 0.0400(10) 0.0037(8) 0.0008(9) -0.0026(9) C12 0.0583(18) 0.0384(11) 0.0288(9) -0.0002(8) -0.0019(10) 0.0043(11) C6 0.0517(18) 0.0422(11) 0.0388(10) 0.0089(9) 0.0018(10) -0.0029(11) C20 0.0497(18) 0.0466(12) 0.0456(11) 0.0053(9) -0.0096(11) -0.0089(11) C3 0.0402(15) 0.0365(10) 0.0367(10) 0.0012(8) 0.0023(9) -0.0017(9) C1 0.0434(16) 0.0302(9) 0.0299(9) -0.0005(7) 0.0036(9) 0.0010(9) C15 0.0457(18) 0.0369(11) 0.0357(10) -0.0004(8) -0.0063(10) -0.0009(11) C13 0.0562(18) 0.0363(10) 0.0335(10) 0.0035(8) 0.0062(10) -0.0029(10) C4 0.0400(16) 0.0461(11) 0.0410(10) 0.0010(9) -0.0052(10) -0.0033(11) C18 0.067(2) 0.0374(11) 0.0523(12) -0.0108(10) -0.0051(12) 0.0059(12) C16 0.0413(16) 0.0330(10) 0.0342(9) -0.0001(8) -0.0033(9) -0.0014(10) C5 0.0514(18) 0.0431(11) 0.0330(10) 0.0041(8) -0.0045(10) 0.0014(11) C21 0.0472(17) 0.0427(11) 0.0394(10) -0.0006(9) -0.0049(10) -0.0003(11) C17 0.0478(17) 0.0382(11) 0.0458(11) -0.0041(9) 0.0003(10) 0.0021(10) C19 0.065(2) 0.0333(11) 0.0505(12) 0.0018(9) -0.0154(12) -0.0055(12) O3 0.0381(10) 0.0310(7) 0.0383(7) -0.0014(5) -0.0078(7) -0.0028(6) O2 0.0405(11) 0.0561(9) 0.0315(7) 0.0071(6) -0.0006(7) -0.0029(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_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag Na1 O1 2.3508(17) . . yes Na1 O4 2.6945(19) . . yes Na1 O5 2.3412(16) . . yes Na1 O2 2.676(2) . 1_655 yes Na1 O3 2.3908(17) . 1_655 yes Na1 O3 2.3416(15) . 3_566 yes O1 C1 1.220(3) . . yes O2 C1 1.327(3) . . yes O3 C8 1.247(3) . . yes O4 C8 1.285(2) . . yes O5 C15 1.223(3) . . yes O6 C15 1.330(3) . . yes O2 H2 0.8200 . . no O6 H6A 0.8200 . . no C1 C2 1.499(3) . . no C2 C7 1.386(3) . . no C2 C3 1.391(3) . . no C3 C4 1.395(3) . . no C4 C5 1.378(3) . . no C5 C6 1.380(3) . . no C6 C7 1.389(3) . . no C8 C9 1.511(3) . . no C9 C14 1.388(3) . . no C9 C10 1.398(3) . . no C10 C11 1.395(3) . . no C11 C12 1.385(3) . . no C12 C13 1.381(3) . . no C13 C14 1.392(3) . . no C15 C16 1.493(3) . . no C16 C21 1.387(3) . . no C16 C17 1.395(3) . . no C17 C18 1.393(3) . . no C18 C19 1.384(4) . . no C19 C20 1.383(4) . . no C20 C21 1.393(3) . . no C3 H3 0.9300 . . no C4 H4 0.9300 . . no C5 H5 0.9300 . . no C6 H6 0.9300 . . no C7 H7 0.9300 . . no C10 H10 0.9300 . . no C11 H11 0.9300 . . no C12 H12 0.9300 . . no C13 H13 0.9300 . . no C14 H14 0.9300 . . no C17 H17 0.9300 . . no C18 H18 0.9300 . . no C19 H19 0.9300 . . no C20 H20 0.9300 . . no C21 H21 0.9300 . . 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 O1 Na1 O4 75.58(6) . . . yes O1 Na1 O5 91.52(6) . . . yes O1 Na1 O2 97.37(6) . . 1_655 yes O1 Na1 O3 173.10(7) . . 1_655 yes O1 Na1 O3 96.24(6) . . 3_566 yes O4 Na1 O5 82.06(6) . . . yes O2 Na1 O4 165.18(6) 1_655 . . yes O3 Na1 O4 111.26(6) 1_655 . . yes O3 Na1 O4 85.72(6) 3_566 . . yes O2 Na1 O5 85.15(6) 1_655 . . yes O3 Na1 O5 90.34(6) 1_655 . . yes O3 Na1 O5 163.43(6) 3_566 . . yes O2 Na1 O3 76.17(6) 1_655 . 1_655 yes O2 Na1 O3 108.23(6) 1_655 . 3_566 yes O3 Na1 O3 83.70(6) 1_655 . 3_566 yes Na1 O1 C1 134.22(13) . . . yes Na1 O2 C1 164.91(14) 1_455 . . yes Na1 O3 C8 126.03(11) 1_455 . . yes Na1 O3 C8 132.90(13) 3_566 . . yes Na1 O3 Na1 96.30(7) 1_455 . 3_566 yes Na1 O4 C8 138.69(13) . . . yes Na1 O5 C15 133.13(16) . . . yes Na1 O2 H2 85.00 1_455 . . no C1 O2 H2 110.00 . . . no C15 O6 H6A 109.00 . . . no O1 C1 O2 122.74(17) . . . yes O1 C1 C2 122.34(19) . . . yes O2 C1 C2 114.92(19) . . . yes C1 C2 C7 117.8(2) . . . no C3 C2 C7 119.70(17) . . . no C1 C2 C3 122.47(18) . . . no C2 C3 C4 119.37(19) . . . no C3 C4 C5 120.3(2) . . . no C4 C5 C6 120.63(19) . . . no C5 C6 C7 119.3(2) . . . no C2 C7 C6 120.7(2) . . . no O4 C8 C9 117.13(19) . . . yes O3 C8 O4 123.47(17) . . . yes O3 C8 C9 119.37(17) . . . yes C8 C9 C10 121.33(18) . . . no C8 C9 C14 119.3(2) . . . no C10 C9 C14 119.39(17) . . . no C9 C10 C11 119.78(19) . . . no C10 C11 C12 120.2(2) . . . no C11 C12 C13 120.10(17) . . . no C12 C13 C14 120.04(19) . . . no C9 C14 C13 120.5(2) . . . no O5 C15 O6 123.03(19) . . . yes O5 C15 C16 123.5(2) . . . yes O6 C15 C16 113.52(18) . . . yes C15 C16 C17 120.9(2) . . . no C15 C16 C21 119.18(19) . . . no C17 C16 C21 119.80(19) . . . no C16 C17 C18 119.7(2) . . . no C17 C18 C19 120.4(2) . . . no C18 C19 C20 119.8(2) . . . no C19 C20 C21 120.3(2) . . . no C16 C21 C20 120.0(2) . . . no C2 C3 H3 120.00 . . . no C4 C3 H3 120.00 . . . no C3 C4 H4 120.00 . . . no C5 C4 H4 120.00 . . . no C4 C5 H5 120.00 . . . no C6 C5 H5 120.00 . . . no C5 C6 H6 120.00 . . . no C7 C6 H6 120.00 . . . no C2 C7 H7 120.00 . . . no C6 C7 H7 120.00 . . . no C9 C10 H10 120.00 . . . no C11 C10 H10 120.00 . . . no C10 C11 H11 120.00 . . . no C12 C11 H11 120.00 . . . no C11 C12 H12 120.00 . . . no C13 C12 H12 120.00 . . . no C12 C13 H13 120.00 . . . no C14 C13 H13 120.00 . . . no C9 C14 H14 120.00 . . . no C13 C14 H14 120.00 . . . no C16 C17 H17 120.00 . . . no C18 C17 H17 120.00 . . . no C17 C18 H18 120.00 . . . no C19 C18 H18 120.00 . . . no C18 C19 H19 120.00 . . . no C20 C19 H19 120.00 . . . no C19 C20 H20 120.00 . . . no C21 C20 H20 120.00 . . . no C16 C21 H21 120.00 . . . no C20 C21 H21 120.00 . . . no loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O6 H6A O4 0.82 1.86 2.675(2) 173.1 1 O2 H2 O4 0.82 1.75 2.5699(19) 176.4 1 O2 H2 O3 0.82 2.60 3.1330(19) 124.2 1 _diffrn_measured_fraction_theta_max 0.946 _diffrn_reflns_theta_full 26.03 _diffrn_measured_fraction_theta_full 0.946 _refine_diff_density_max 0.224 _refine_diff_density_min -0.263 _refine_diff_density_rms 0.051