#------------------------------------------------------------------------------ #$Date: 2008-04-05 09:13:02 +0100 (Sat, 05 Apr 2008) $ #$Revision: 340 $ #$URL: svn://www.crystallography.net/cod/cif/2/2102026.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/. The original data for this entry # were provided by IUCr Journals, http://journals.iucr.org/. # # The file may be used within the scientific community so long as # proper attribution is given to the journal article from which the # data were obtained. # data_2102026 loop_ _publ_author_name 'Lough, Alan J.' 'Wheatley, Paul S.' 'Ferguson, George' 'Glidewell, Christopher' _publ_section_title ; Hydrogen-bonding Behaviour of Benzene-1,2,4,5-tetracarboxylic Acid: Supramolecular Structures of Different Dimensionality in the 2:1 Adducts Formed with 4,4'-Bipyridyl and Hexamethylenetetramine. ; _journal_issue 2 _journal_name_full 'Acta Crystallographica, Section B' _journal_page_first 261 _journal_page_last 272 _journal_volume 56 _journal_year 2000 _chemical_formula_moiety 'C10 H4 O8, 2(C10 H9 N2)' _chemical_formula_sum 'C30 H22 N4 O8' _chemical_formula_weight 566.52 _chemical_name_systematic ; Benzene-1,2,4,5-tetracarboxylic acid--4,4'-bipyridyl (1/2) ; _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _cell_angle_alpha 64.872(2) _cell_angle_beta 72.375(2) _cell_angle_gamma 76.612(2) _cell_formula_units_Z 1 _cell_length_a 7.3974(3) _cell_length_b 9.6352(4) _cell_length_c 10.1688(3) _cell_measurement_reflns_used 2832 _cell_measurement_temperature 100.0(10) _cell_measurement_theta_max 27.47 _cell_measurement_theta_min 2.91 _cell_volume 620.92(4) _computing_cell_refinement 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_data_collection 'Kappa-CCD server software (Nonius, 1997)' _computing_data_reduction 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_molecular_graphics 'NRCVAX-96, ORTEP (Johnson, 1976), PLATON (Spek, 1999)' _computing_publication_material 'NRCVAX-96, SHELXL-97 and WordPerfect macro PRPKAPPA (Ferguson, 1999)' _computing_structure_refinement 'NRCVAX-96 and SHELXL-97 (Sheldrick, 1997b)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997a)' _diffrn_ambient_temperature 100.0(10) _diffrn_measured_fraction_theta_full .994 _diffrn_measured_fraction_theta_max .994 _diffrn_measurement_device_type Kappa-CCD _diffrn_measurement_method '\f scans and \w scans with \k offsets' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed X-ray tube' _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength .71073 _diffrn_reflns_av_R_equivalents .031 _diffrn_reflns_av_sigmaI/netI .0331 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_number 9749 _diffrn_reflns_theta_full 27.47 _diffrn_reflns_theta_max 27.47 _diffrn_reflns_theta_min 2.91 _diffrn_standards_decay_% negligible _exptl_absorpt_coefficient_mu .112 _exptl_absorpt_correction_T_max .9725 _exptl_absorpt_correction_T_min .9618 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_process_details 'DENZO-SMN (Otwinowski & Minor, 1997)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.515 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 294 _exptl_crystal_size_max .35 _exptl_crystal_size_mid .27 _exptl_crystal_size_min .25 _refine_diff_density_max .259 _refine_diff_density_min -.328 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.082 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 195 _refine_ls_number_reflns 2832 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.082 _refine_ls_R_factor_all .0495 _refine_ls_R_factor_gt .0378 _refine_ls_shift/su_max .000 _refine_ls_shift/su_mean .000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0668P)^2^+0.0415P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref .1076 _reflns_number_gt 2272 _reflns_number_total 2832 _reflns_threshold_expression >2\s(I) _[local]_cod_data_source_file fr0006.cif loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N .0061 .0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O .0106 .0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_type_symbol O1 .89461(12) .33319(11) .69494(10) .0244(2) Uani d . 1 O O2 .62864(13) .39029(10) .85042(9) .0224(2) Uani d . 1 O O3 .37571(14) .18225(10) .85695(10) .0263(2) Uani d . 1 O O4 .19766(12) .39660(10) .88158(9) .0205(2) Uani d . 1 O C1 .60774(17) .44064(13) .60813(13) .0164(3) Uani d . 1 C C2 .41449(17) .41918(13) .64906(12) .0161(3) Uani d . 1 C C3 .30717(17) .47916(14) .54099(13) .0164(2) Uani d . 1 C C4 .72470(17) .38134(13) .72521(13) .0167(3) Uani d . 1 C C5 .32697(17) .32045(14) .80765(13) .0175(3) Uani d . 1 C N11 .71608(14) .22555(12) 1.09709(11) .0192(2) Uani d . 1 N C12 .64796(19) .28313(15) 1.20399(14) .0213(3) Uani d . 1 C C13 .66643(18) .19471(14) 1.34885(14) .0206(3) Uani d . 1 C C14 .75572(16) .04318(14) 1.38655(13) .0164(3) Uani d . 1 C C15 .82308(18) -.01395(15) 1.27304(14) .0216(3) Uani d . 1 C C16 .79949(18) .08063(15) 1.13010(14) .0227(3) Uani d . 1 C N21 .81740(15) -.23338(12) 1.83499(11) .0198(2) Uani d . 1 N C22 .89003(17) -.28840(14) 1.72634(13) .0200(3) Uani d . 1 C C23 .87378(17) -.20332(14) 1.57999(13) .0194(3) Uani d . 1 C C24 .77721(16) -.05421(14) 1.54222(13) .0167(3) Uani d . 1 C C25 .70016(18) .00166(15) 1.65650(13) .0211(3) Uani d . 1 C C26 .72364(18) -.09065(15) 1.79933(14) .0216(3) Uani d . 1 C H4 .1829 .3445 .9737 .031 Uiso calc R 1 H H3 .1759 .4653 .5691 .020 Uiso calc R 1 H H11 .692(3) .306(2) .972(2) .066(6) Uiso d . 1 H H12 .5862 .3859 1.1801 .026 Uiso calc R 1 H H13 .6179 .2376 1.4232 .025 Uiso calc R 1 H H15 .8845 -.1166 1.2934 .026 Uiso calc R 1 H H16 .8442 .0407 1.0536 .027 Uiso calc R 1 H H22 .9555 -.3901 1.7505 .024 Uiso calc R 1 H H23 .9281 -.2464 1.5061 .023 Uiso calc R 1 H H25 .6322 .1023 1.6363 .025 Uiso calc R 1 H H26 .6707 -.0508 1.8757 .026 Uiso calc R 1 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 O1 .0205(5) .0308(5) .0208(5) .0039(4) -.0078(4) -.0103(4) O2 .0252(5) .0264(5) .0141(4) .0061(4) -.0088(3) -.0080(4) O3 .0396(6) .0170(5) .0163(4) -.0017(4) -.0029(4) -.0042(4) O4 .0221(5) .0223(5) .0115(4) .0021(4) -.0031(3) -.0042(3) C1 .0204(6) .0144(6) .0146(6) .0016(4) -.0066(4) -.0060(4) C2 .0209(6) .0133(6) .0130(5) .0003(5) -.0039(4) -.0052(4) C3 .0166(6) .0167(6) .0156(6) .0000(5) -.0045(4) -.0064(5) C4 .0195(6) .0148(6) .0151(5) .0005(5) -.0061(5) -.0049(4) C5 .0194(6) .0186(6) .0140(5) -.0016(5) -.0053(4) -.0052(5) N11 .0207(5) .0202(6) .0159(5) -.0011(4) -.0072(4) -.0047(4) C12 .0263(7) .0175(6) .0192(6) .0005(5) -.0094(5) -.0051(5) C13 .0264(7) .0190(6) .0170(6) .0009(5) -.0074(5) -.0077(5) C14 .0161(6) .0174(6) .0149(6) -.0022(5) -.0057(4) -.0039(5) C15 .0260(7) .0176(6) .0195(6) .0038(5) -.0083(5) -.0066(5) C16 .0267(7) .0234(7) .0170(6) .0034(5) -.0074(5) -.0085(5) N21 .0200(5) .0205(6) .0154(5) -.0019(4) -.0039(4) -.0040(4) C22 .0208(6) .0181(6) .0173(6) .0015(5) -.0058(5) -.0043(5) C23 .0210(6) .0197(6) .0160(6) .0007(5) -.0048(5) -.0066(5) C24 .0156(6) .0173(6) .0154(6) -.0026(5) -.0043(4) -.0038(5) C25 .0255(7) .0177(6) .0176(6) .0006(5) -.0060(5) -.0053(5) C26 .0259(7) .0214(7) .0154(6) .0002(5) -.0051(5) -.0064(5) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag O1 C4 . 1.228(2) no O2 C4 . 1.285(2) no O3 C5 . 1.214(2) no O4 C5 . 1.314(2) no C1 C3 2_666 1.3946(16) no C1 C2 . 1.4011(17) no C1 C4 . 1.5197(15) no C2 C3 . 1.3958(16) no C2 C5 . 1.5083(15) no C3 C1 2_666 1.3946(16) no N11 C16 . 1.331(2) no N11 C12 . 1.340(2) no C12 C13 . 1.3844(17) no C13 C14 . 1.3951(18) no C14 C15 . 1.3956(17) no C14 C24 . 1.4945(16) no C15 C16 . 1.3888(16) no N21 C26 . 1.338(2) no N21 C22 . 1.340(2) no C22 C23 . 1.3885(16) no C23 C24 . 1.3944(17) no C24 C25 . 1.3975(16) no C25 C26 . 1.3838(17) no loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_publ_flag C3 C1 C2 119.80(10) no C3 C1 C4 119.50(10) no C2 C1 C4 120.70(10) no C3 C2 C1 120.00(10) no C3 C2 C5 120.00(10) no C1 C2 C5 119.80(10) no C1 C3 C2 120.2(2) no O1 C4 O2 126.40(10) no O1 C4 C1 120.24(10) no O2 C4 C1 113.39(10) no O3 C5 O4 125.30(10) no O3 C5 C2 120.35(11) no O4 C5 C2 114.40(10) no C16 N11 C12 120.00(10) no N11 C12 C13 120.84(12) no C12 C13 C14 120.52(12) no C15 C14 C13 117.22(11) no C15 C14 C24 121.40(11) no C13 C14 C24 121.37(11) no C16 C15 C14 119.39(11) no N11 C16 C15 121.98(11) no C26 N21 C22 117.80(10) no N21 C22 C23 122.89(11) no C22 C23 C24 119.51(11) no C23 C24 C25 117.23(11) no C23 C24 C14 121.98(11) no C25 C24 C14 120.79(11) no C26 C25 C24 119.51(12) no N21 C26 C25 123.10(11) no 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_site_symmetry_1 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag C3 C1 C2 C3 2_666 . -.58(19) no C4 C1 C2 C3 . . 177.69(10) no C3 C1 C2 C5 2_666 . 174.53(10) no C4 C1 C2 C5 . . -7.20(16) no C1 C2 C3 C1 . 2_666 .59(19) no C5 C2 C3 C1 . 2_666 -174.52(10) no C3 C1 C4 O1 2_666 . -35.92(17) no C2 C1 C4 O1 . . 145.8(2) no C3 C1 C4 O2 2_666 . 143.10(11) no C2 C1 C4 O2 . . -35.2(2) no C3 C2 C5 O3 . . 107.54(14) no C1 C2 C5 O3 . . -67.6(2) no C3 C2 C5 O4 . . -71.76(14) no C1 C2 C5 O4 . . 113.1(2) no C16 N11 C12 C13 . . 1.33(18) no N11 C12 C13 C14 . . -.36(19) no C12 C13 C14 C15 . . -.40(18) no C12 C13 C14 C24 . . 179.98(11) no C13 C14 C15 C16 . . .21(18) no C24 C14 C15 C16 . . 179.83(11) no C12 N11 C16 C15 . . -1.54(19) no C14 C15 C16 N11 . . .76(19) no C26 N21 C22 C23 . . .80(18) no N21 C22 C23 C24 . . -.41(19) no C22 C23 C24 C25 . . -.28(17) no C22 C23 C24 C14 . . 179.75(11) no C15 C14 C24 C23 . . 3.39(18) no C13 C14 C24 C23 . . -177.01(11) no C15 C14 C24 C25 . . -176.58(11) no C13 C14 C24 C25 . . 3.03(17) no C23 C24 C25 C26 . . .55(17) no C14 C24 C25 C26 . . -179.48(11) no C22 N21 C26 C25 . . -.50(18) no C24 C25 C26 N21 . . -.17(19) no loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_publ_flag O4 H4 N21 2_658 .84 1.78 2.6134(13) 173 yes N11 H11 O2 . 1.22(2) 1.32(2) 2.5210(13) 168(2) yes C3 H3 O1 1_455 .95 2.41 3.312(2) 158 yes C12 H12 O2 2_667 .95 2.33 3.259(2) 167 yes C15 H15 O1 2_757 .95 2.32 3.243(2) 165 yes