# Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 2001 data_2TMA.1THB _database_code_CSD 164336 _journal_coden_Cambridge 440 _publ_requested_journal 'New Journal of Chemistry' loop_ _publ_author_name 'Liu, R.' 'Mok, K.-F.' 'Valiyaveettil, Suresh' _publ_contact_author_name 'Dr Suresh Valiyaveettil' _publ_contact_author_address ; Dr Suresh Valiyaveettil Department of Chemistry National University of Singapore 3 Science Drive 3 173543 SINGAPORE ; _publ_contact_author_email 'CHMSV@NUS.EDU.SG' _publ_section_title ; Solid-State Self-Assembly of a Complex From 1,3,5-Benzenetricarboxylic Acid and 1,3,5-Trihydroxybenzene: Influence of Strong o-H...O and C-H...O Hydrogen Bonds ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'Trimesic acid. phloroglucinol' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H18 O15' _chemical_formula_weight 546.38 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.1504(1) _cell_length_b 13.5269(2) _cell_length_c 13.5587(2) _cell_angle_alpha 63.756(1) _cell_angle_beta 80.888(1) _cell_angle_gamma 81.243(1) _cell_volume 1156.39(3) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description Prism _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.569 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 564 _exptl_absorpt_coefficient_mu 0.134 _exptl_absorpt_correction_type 'Sadabs (Sheldrick, 1996)' _exptl_absorpt_correction_T_min 0.782 _exptl_absorpt_correction_T_max 0.977 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10566 _diffrn_reflns_av_R_equivalents 0.0143 _diffrn_reflns_av_sigmaI/netI 0.0238 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.80 _diffrn_reflns_theta_max 28.26 _reflns_number_total 5447 _reflns_number_gt 4453 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Siemens XSCANS' _computing_cell_refinement 'Siemens XSCANS' _computing_data_reduction 'Siemens SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Siemens SHELXTL' _computing_publication_material 'Siemens 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^)+(0.0692P)^2^+0.0921P] 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 5447 _refine_ls_number_parameters 352 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0447 _refine_ls_R_factor_gt 0.0368 _refine_ls_wR_factor_ref 0.1112 _refine_ls_wR_factor_gt 0.1069 _refine_ls_goodness_of_fit_ref 1.062 _refine_ls_restrained_S_all 1.062 _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 C1A C 1.02583(16) 0.64016(9) 1.07871(9) 0.0253(2) Uani 1 1 d . . . C2A C 0.97053(16) 0.75305(9) 1.02457(9) 0.0262(2) Uani 1 1 d . . . H2AA H 1.0061 0.7916 0.9493 0.031 Uiso 1 1 calc R . . C3A C 0.86214(16) 0.80816(9) 1.08308(9) 0.0250(2) Uani 1 1 d . . . C4A C 0.80919(16) 0.75041(9) 1.19598(9) 0.0256(2) Uani 1 1 d . . . H4AA H 0.7376 0.7873 1.2352 0.031 Uiso 1 1 calc R . . C5A C 0.86350(16) 0.63761(9) 1.24990(9) 0.0251(2) Uani 1 1 d . . . C6A C 0.97185(16) 0.58231(9) 1.19141(9) 0.0259(2) Uani 1 1 d . . . H6AA H 1.0081 0.5069 1.2275 0.031 Uiso 1 1 calc R . . C7A C 1.14514(17) 0.58040(9) 1.01794(9) 0.0275(2) Uani 1 1 d . . . C8A C 0.80184(17) 0.92830(9) 1.02374(9) 0.0285(2) Uani 1 1 d . . . C9A C 0.80466(17) 0.57723(9) 1.37032(9) 0.0287(2) Uani 1 1 d . . . O1A O 1.19294(14) 0.48147(7) 1.05853(7) 0.0366(2) Uani 1 1 d . . . O2A O 1.19558(15) 0.64641(7) 0.91399(7) 0.0434(3) Uani 1 1 d . . . H2AB H 1.2604 0.6101 0.8837 0.065 Uiso 1 1 calc R . . O3A O 0.84979(15) 0.98481(7) 0.92678(7) 0.0411(2) Uani 1 1 d . . . O4A O 0.69034(15) 0.96842(7) 1.08714(7) 0.0439(3) Uani 1 1 d . . . H4AB H 0.6626 1.0348 1.0512 0.066 Uiso 1 1 calc R . . O5A O 0.71066(15) 0.62006(8) 1.42663(7) 0.0400(2) Uani 1 1 d . . . O6A O 0.86497(16) 0.47145(7) 1.41057(7) 0.0481(3) Uani 1 1 d . . . H6AB H 0.8284 0.4416 1.4767 0.072 Uiso 1 1 calc R . . C10A C 0.42953(17) 0.72780(9) 1.09427(9) 0.0261(2) Uani 1 1 d . . . C11A C 0.33260(17) 0.74332(9) 1.18411(9) 0.0273(2) Uani 1 1 d . . . H11A H 0.2795 0.8130 1.1770 0.033 Uiso 1 1 calc R . . C12A C 0.31772(17) 0.65093(9) 1.28513(9) 0.0266(2) Uani 1 1 d . . . C13A C 0.39939(18) 0.54641(9) 1.29852(9) 0.0293(2) Uani 1 1 d . . . H13A H 0.3888 0.4856 1.3669 0.035 Uiso 1 1 calc R . . C14A C 0.49747(17) 0.53586(9) 1.20623(10) 0.0276(2) Uani 1 1 d . . . C15A C 0.51308(17) 0.62492(9) 1.10298(9) 0.0273(2) Uani 1 1 d . . . H15A H 0.5772 0.6161 1.0417 0.033 Uiso 1 1 calc R . . O7A O 0.44087(14) 0.81986(7) 0.99427(7) 0.0390(2) Uani 1 1 d . . . H7AA H 0.5065 0.8030 0.9477 0.058 Uiso 1 1 calc R . . O8A O 0.21850(14) 0.65966(7) 1.37699(7) 0.0384(2) Uani 1 1 d . . . H8AA H 0.1635 0.7220 1.3589 0.058 Uiso 1 1 calc R . . O9A O 0.58481(16) 0.43496(7) 1.21451(7) 0.0431(3) Uani 1 1 d . . . H9AA H 0.5763 0.3896 1.2795 0.065 Uiso 1 1 calc R . . C1B C 0.15881(16) 1.03968(9) 0.56438(9) 0.0245(2) Uani 1 1 d . . . C2B C 0.24366(16) 0.93665(9) 0.57308(9) 0.0255(2) Uani 1 1 d . . . H2BA H 0.2394 0.8755 0.6414 0.031 Uiso 1 1 calc R . . C3B C 0.33503(16) 0.92537(9) 0.47921(9) 0.0245(2) Uani 1 1 d . . . C4B C 0.34191(16) 1.01687(9) 0.37671(9) 0.0263(2) Uani 1 1 d . . . H4BA H 0.4034 1.0094 0.3143 0.032 Uiso 1 1 calc R . . C5B C 0.25609(16) 1.11997(9) 0.36811(9) 0.0262(2) Uani 1 1 d . . . C6B C 0.16476(16) 1.13158(9) 0.46149(9) 0.0264(2) Uani 1 1 d . . . H6BA H 0.1078 1.2003 0.4555 0.032 Uiso 1 1 calc R . . C7B C 0.05809(17) 1.05486(9) 0.66252(9) 0.0288(2) Uani 1 1 d . . . C8B C 0.42657(18) 0.81378(9) 0.49235(10) 0.0292(2) Uani 1 1 d . . . C9B C 0.26600(19) 1.21638(10) 0.25708(10) 0.0334(3) Uani 1 1 d . . . O1B O -0.02146(16) 1.14206(8) 0.65722(8) 0.0476(3) Uani 1 1 d . . . O2B O 0.06183(17) 0.96317(8) 0.75480(7) 0.0484(3) Uani 1 1 d . . . H2BB H 0.0031 0.9755 0.8058 0.073 Uiso 1 1 calc R . . O3B O 0.41959(19) 0.73302(8) 0.57952(8) 0.0549(3) Uani 1 1 d . . . O4B O 0.51809(15) 0.81361(7) 0.40027(8) 0.0421(2) Uani 1 1 d . . . H4BB H 0.5708 0.7516 0.4127 0.063 Uiso 1 1 calc R . . O5B O 0.3513(2) 1.21034(9) 0.17578(9) 0.0651(4) Uani 1 1 d . . . O6B O 0.17224(18) 1.30744(8) 0.25682(8) 0.0534(3) Uani 1 1 d . . . H6BB H 0.1874 1.3582 0.1949 0.080 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 C1A 0.0314(5) 0.0207(5) 0.0205(5) -0.0087(4) 0.0021(4) 0.0020(4) C2A 0.0340(6) 0.0209(5) 0.0187(5) -0.0071(4) 0.0030(4) 0.0018(4) C3A 0.0316(5) 0.0186(5) 0.0203(5) -0.0069(4) 0.0016(4) 0.0017(4) C4A 0.0322(5) 0.0209(5) 0.0205(5) -0.0093(4) 0.0022(4) 0.0027(4) C5A 0.0315(5) 0.0207(5) 0.0191(5) -0.0074(4) 0.0015(4) 0.0016(4) C6A 0.0334(6) 0.0187(5) 0.0209(5) -0.0072(4) 0.0014(4) 0.0024(4) C7A 0.0373(6) 0.0204(5) 0.0200(5) -0.0078(4) 0.0024(4) 0.0029(4) C8A 0.0372(6) 0.0207(5) 0.0218(5) -0.0078(4) 0.0031(4) 0.0037(4) C9A 0.0390(6) 0.0209(5) 0.0203(5) -0.0076(4) 0.0026(4) 0.0042(4) O1A 0.0557(6) 0.0203(4) 0.0253(4) -0.0083(3) 0.0039(4) 0.0074(4) O2A 0.0693(7) 0.0232(4) 0.0228(4) -0.0071(3) 0.0152(4) 0.0095(4) O3A 0.0624(6) 0.0237(4) 0.0222(4) -0.0044(3) 0.0101(4) 0.0069(4) O4A 0.0673(6) 0.0207(4) 0.0258(4) -0.0048(3) 0.0129(4) 0.0128(4) O5A 0.0594(6) 0.0273(4) 0.0232(4) -0.0102(4) 0.0072(4) 0.0106(4) O6A 0.0798(7) 0.0226(4) 0.0215(4) -0.0028(4) 0.0129(4) 0.0143(4) C10A 0.0336(6) 0.0192(5) 0.0194(5) -0.0054(4) 0.0009(4) 0.0021(4) C11A 0.0358(6) 0.0180(5) 0.0229(5) -0.0080(4) 0.0021(4) 0.0043(4) C12A 0.0337(6) 0.0233(5) 0.0196(5) -0.0097(4) 0.0036(4) 0.0020(4) C13A 0.0397(6) 0.0206(5) 0.0201(5) -0.0062(4) 0.0048(5) 0.0027(4) C14A 0.0359(6) 0.0190(5) 0.0240(5) -0.0096(4) 0.0020(4) 0.0048(4) C15A 0.0352(6) 0.0222(5) 0.0209(5) -0.0101(4) 0.0038(4) 0.0037(4) O7A 0.0619(6) 0.0211(4) 0.0189(4) -0.0038(3) 0.0105(4) 0.0092(4) O8A 0.0590(6) 0.0231(4) 0.0212(4) -0.0077(3) 0.0097(4) 0.0102(4) O9A 0.0698(6) 0.0197(4) 0.0239(4) -0.0056(3) 0.0107(4) 0.0131(4) C1B 0.0293(5) 0.0226(5) 0.0204(5) -0.0103(4) 0.0012(4) 0.0010(4) C2B 0.0318(5) 0.0210(5) 0.0211(5) -0.0086(4) 0.0002(4) 0.0006(4) C3B 0.0291(5) 0.0199(5) 0.0230(5) -0.0101(4) 0.0006(4) 0.0014(4) C4B 0.0314(5) 0.0232(5) 0.0219(5) -0.0105(4) 0.0031(4) 0.0008(4) C5B 0.0323(6) 0.0204(5) 0.0209(5) -0.0069(4) 0.0015(4) 0.0011(4) C6B 0.0317(6) 0.0205(5) 0.0237(5) -0.0093(4) 0.0007(4) 0.0028(4) C7B 0.0363(6) 0.0248(5) 0.0232(5) -0.0118(5) 0.0017(5) 0.0025(4) C8B 0.0388(6) 0.0206(5) 0.0251(5) -0.0096(4) 0.0012(5) 0.0011(4) C9B 0.0451(7) 0.0250(6) 0.0218(5) -0.0076(5) 0.0064(5) 0.0033(5) O1B 0.0708(7) 0.0287(5) 0.0338(5) -0.0151(4) 0.0083(5) 0.0136(5) O2B 0.0799(7) 0.0310(5) 0.0203(4) -0.0086(4) 0.0098(4) 0.0121(5) O3B 0.0912(8) 0.0219(4) 0.0300(5) -0.0022(4) 0.0108(5) 0.0105(5) O4B 0.0637(6) 0.0239(4) 0.0302(5) -0.0128(4) 0.0081(4) 0.0111(4) O5B 0.1048(10) 0.0370(6) 0.0265(5) -0.0058(4) 0.0241(6) 0.0138(6) O6B 0.0865(8) 0.0243(5) 0.0259(5) -0.0014(4) 0.0095(5) 0.0167(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 C1A C2A 1.3942(15) . ? C1A C6A 1.3943(15) . ? C1A C7A 1.4887(15) . ? C2A C3A 1.3923(15) . ? C3A C4A 1.3949(15) . ? C3A C8A 1.4881(15) . ? C4A C5A 1.3915(15) . ? C5A C6A 1.3937(15) . ? C5A C9A 1.4891(15) . ? C7A O1A 1.2164(14) . ? C7A O2A 1.3183(14) . ? C8A O3A 1.2159(14) . ? C8A O4A 1.3163(14) . ? C9A O5A 1.2167(14) . ? C9A O6A 1.3143(14) . ? C10A O7A 1.3778(13) . ? C10A C11A 1.3867(16) . ? C10A C15A 1.3897(15) . ? C11A C12A 1.3892(15) . ? C12A O8A 1.3760(13) . ? C12A C13A 1.3885(15) . ? C13A C14A 1.3884(16) . ? C14A O9A 1.3757(13) . ? C14A C15A 1.3869(15) . ? C1B C2B 1.3944(15) . ? C1B C6B 1.3989(15) . ? C1B C7B 1.4915(15) . ? C2B C3B 1.3957(15) . ? C3B C4B 1.3933(15) . ? C3B C8B 1.4956(15) . ? C4B C5B 1.3976(15) . ? C5B C6B 1.3917(15) . ? C5B C9B 1.4934(16) . ? C7B O1B 1.2057(15) . ? C7B O2B 1.3162(14) . ? C8B O3B 1.2037(15) . ? C8B O4B 1.3154(14) . ? C9B O5B 1.2021(15) . ? C9B O6B 1.3084(15) . ? 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 C2A C1A C6A 119.99(10) . . ? C2A C1A C7A 120.75(10) . . ? C6A C1A C7A 119.25(10) . . ? C3A C2A C1A 120.04(10) . . ? C2A C3A C4A 119.96(10) . . ? C2A C3A C8A 119.37(10) . . ? C4A C3A C8A 120.67(10) . . ? C5A C4A C3A 120.01(10) . . ? C4A C5A C6A 120.09(10) . . ? C4A C5A C9A 119.23(10) . . ? C6A C5A C9A 120.68(10) . . ? C5A C6A C1A 119.91(10) . . ? O1A C7A O2A 122.76(10) . . ? O1A C7A C1A 124.46(10) . . ? O2A C7A C1A 112.78(10) . . ? O3A C8A O4A 122.73(11) . . ? O3A C8A C3A 124.17(10) . . ? O4A C8A C3A 113.11(10) . . ? O5A C9A O6A 122.83(11) . . ? O5A C9A C5A 124.28(11) . . ? O6A C9A C5A 112.89(10) . . ? O7A C10A C11A 116.95(10) . . ? O7A C10A C15A 120.65(10) . . ? C11A C10A C15A 122.41(10) . . ? C10A C11A C12A 117.56(10) . . ? O8A C12A C13A 116.97(10) . . ? O8A C12A C11A 120.67(10) . . ? C13A C12A C11A 122.36(10) . . ? C14A C13A C12A 117.69(10) . . ? O9A C14A C15A 117.20(10) . . ? O9A C14A C13A 120.51(10) . . ? C15A C14A C13A 122.28(10) . . ? C14A C15A C10A 117.68(10) . . ? C2B C1B C6B 119.96(10) . . ? C2B C1B C7B 121.59(10) . . ? C6B C1B C7B 118.45(10) . . ? C1B C2B C3B 119.98(10) . . ? C4B C3B C2B 120.17(10) . . ? C4B C3B C8B 121.52(10) . . ? C2B C3B C8B 118.31(10) . . ? C3B C4B C5B 119.75(10) . . ? C6B C5B C4B 120.27(10) . . ? C6B C5B C9B 121.31(10) . . ? C4B C5B C9B 118.43(10) . . ? C5B C6B C1B 119.87(10) . . ? O1B C7B O2B 123.55(11) . . ? O1B C7B C1B 123.21(11) . . ? O2B C7B C1B 113.24(10) . . ? O3B C8B O4B 123.78(11) . . ? O3B C8B C3B 122.82(11) . . ? O4B C8B C3B 113.39(10) . . ? O5B C9B O6B 123.42(12) . . ? O5B C9B C5B 122.98(11) . . ? O6B C9B C5B 113.60(10) . . ? _diffrn_measured_fraction_theta_max 0.952 _diffrn_reflns_theta_full 28.26 _diffrn_measured_fraction_theta_full 0.952 _refine_diff_density_max 0.314 _refine_diff_density_min -0.197 _refine_diff_density_rms 0.043