data_2202097
_journal_name_full  'Acta Crystallographica, Section E'
_journal_year  2003
_journal_volume  59
_journal_page_first  o14
_journal_page_last  o17
_publ_section_title
;
Hydrogen-bonded supramolecular motifs in
trimethoprim--terephthalate--terephthalic acid (2/1/1)
;
loop_
_publ_author_name
  'Madhukar Hemamalini'
  'Packianathan Thomas Muthiah'
  'Gabriele Bocelli'
  'Andrea Cantoni'
_chemical_name_common  'Trimethoprim terephthalate terephthalic acid'
_chemical_formula_moiety  '2C14 H19 N4 O3 +, C8 H4 O4 2-, C8 H6 O4'
_chemical_formula_sum  'C44 H48 N8 O14'
_chemical_formula_structural  '(C14 H19 N4 O3 +)2, (C8 H4 O4 2-), (C8 H6 O4)'
_chemical_formula_iupac  '2C14 H19 N4 O3 +, C8 H4 O4 2-, C8 H6 O4'
_chemical_formula_weight  912.90
_symmetry_cell_setting  triclinic
_symmetry_space_group_name_H-M  'P -1'
_symmetry_space_group_name_Hall  '-P 1'
loop_
_symmetry_equiv_pos_as_xyz
  x,y,z
  -x,-y,-z
_cell_length_a  8.438(2)
_cell_length_b  10.760(3)
_cell_length_c  12.538(3)
_cell_angle_alpha  90.26(3)
_cell_angle_beta  98.22(2)
_cell_angle_gamma  109.54(3)
_cell_volume  1060.1(5)
_cell_formula_units_Z  1
_cell_measurement_temperature  293(2)
_exptl_crystal_density_diffrn  1.430
_diffrn_ambient_temperature  293(2)
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_type_symbol
  O1 1.00440(13) 0.79830(10) -0.18758(6) 0.0507(3) Uani . . 1.000 O
  O2 0.74369(12) 0.88198(9) -0.17815(7) 0.0490(3) Uani . . 1.000 O
  O3 0.63677(12) 0.90440(10) 0.01253(7) 0.0490(3) Uani . . 1.000 O
  N1 0.88613(12) 0.58973(9) 0.41553(7) 0.0346(3) Uani . . 1.000 N
  N2 0.80617(19) 0.64306(12) 0.57152(11) 0.0585(4) Uani . . 1.000 N
  N3 0.93818(13) 0.81242(9) 0.46848(7) 0.0363(3) Uani . . 1.000 N
  N4 1.06430(15) 0.97817(9) 0.36357(8) 0.0400(3) Uani . . 1.000 N
  C1' 1.01150(14) 0.80973(10) 0.10758(8) 0.0299(3) Uani . . 1.000 C
  C2 0.87713(15) 0.68364(11) 0.48445(9) 0.0359(3) Uani . . 1.000 C
  C2' 1.05884(15) 0.79090(11) 0.00852(8) 0.0337(3) Uani . . 1.000 C
  C3' 0.96597(15) 0.81236(11) -0.08673(8) 0.0360(3) Uani . . 1.000 C
  C4 1.01079(14) 0.84885(10) 0.37984(8) 0.0303(3) Uani . . 1.000 C
  C4' 0.82701(15) 0.85270(11) -0.08314(8) 0.0367(3) Uani . . 1.000 C
  C5 1.03176(13) 0.75525(10) 0.30621(7) 0.0289(3) Uani . . 1.000 C
  C5' 0.77713(14) 0.86766(11) 0.01569(9) 0.0349(3) Uani . . 1.000 C
  C6 0.96769(14) 0.62701(10) 0.32926(8) 0.0329(3) Uani . . 1.000 C
  C6' 0.86970(14) 0.84624(11) 0.11112(8) 0.0330(3) Uani . . 1.000 C
  C7 1.12145(14) 0.79363(11) 0.21017(8) 0.0331(3) Uani . . 1.000 C
  C8 1.1259(2) 0.73478(18) -0.19545(13) 0.0597(5) Uani . . 1.000 C
  C9 0.5900(2) 0.78103(17) -0.22205(13) 0.0564(5) Uani . . 1.000 C
  C10 0.5755(2) 0.91176(17) 0.11107(13) 0.0538(5) Uani . . 1.000 C
  O6 0.23344(14) 0.52107(11) 0.20026(9) 0.0623(4) Uani . . 1.000 O
  O7 0.50441(14) 0.61545(12) 0.27364(9) 0.0615(3) Uani . . 1.000 O
  C15 0.44560(15) 0.52733(11) 0.09379(10) 0.0380(3) Uani . . 1.000 C
  C16 0.33209(17) 0.49069(13) -0.00236(11) 0.0438(4) Uani . . 1.000 C
  C17 0.61367(16) 0.53640(13) 0.09574(11) 0.0440(3) Uani . . 1.000 C
  C18 0.38252(17) 0.55372(11) 0.19391(11) 0.0430(4) Uani . . 1.000 C
  O4 0.37808(14) 0.63900(8) 0.44246(8) 0.0528(3) Uani . . 1.000 O
  O5 0.24182(12) 0.67291(8) 0.57057(7) 0.0422(3) Uani . . 1.000 O
  C11 0.42420(13) 0.86223(9) 0.50146(8) 0.0296(3) Uani . . 1.000 C
  C12 0.37825(15) 0.94741(11) 0.56479(9) 0.0363(3) Uani . . 1.000 C
  C13 0.54704(15) 0.91618(11) 0.43632(9) 0.0367(3) Uani . . 1.000 C
  C14 0.34234(14) 0.71427(10) 0.50504(8) 0.0311(3) Uani . . 1.000 C
  H1 0.835(2) 0.4948(17) 0.4289(13) 0.061(5) Uiso . . 1.000 H
  H6 0.9727(16) 0.5556(13) 0.2855(11) 0.034(3) Uiso . . 1.000 H
  H2 1.1545(18) 0.7642(14) 0.0086(11) 0.041(3) Uiso . . 1.000 H
  H2A 0.747(2) 0.5557(19) 0.5743(14) 0.063(5) Uiso . . 1.000 H
  H2B 0.809(2) 0.7030(19) 0.6193(15) 0.066(5) Uiso . . 1.000 H
  H4A 1.108(2) 1.0058(16) 0.3073(14) 0.052(4) Uiso . . 1.000 H
  H4B 1.0494(19) 1.0341(16) 0.4098(13) 0.049(4) Uiso . . 1.000 H
  H6' 0.8349(18) 0.8617(14) 0.1816(12) 0.045(4) Uiso . . 1.000 H
  H7A 1.167(2) 0.7250(16) 0.1934(12) 0.052(4) Uiso . . 1.000 H
  H7B 1.224(2) 0.8833(16) 0.2283(12) 0.049(4) Uiso . . 1.000 H
  H8A 1.242(2) 0.7897(18) -0.1523(15) 0.063(5) Uiso . . 1.000 H
  H8B 1.136(2) 0.7296(18) -0.2665(16) 0.069(5) Uiso . . 1.000 H
  H8C 1.085(2) 0.645(2) -0.1632(15) 0.074(5) Uiso . . 1.000 H
  H9A 0.618(3) 0.706(3) -0.2490(19) 0.105(8) Uiso . . 1.000 H
  H9B 0.533(3) 0.810(2) -0.2799(19) 0.091(6) Uiso . . 1.000 H
  H9C 0.514(3) 0.746(2) -0.1731(17) 0.079(6) Uiso . . 1.000 H
  H10A 0.482(3) 0.9395(19) 0.0951(15) 0.072(5) Uiso . . 1.000 H
  H10B 0.543(2) 0.8251(19) 0.1458(14) 0.066(5) Uiso . . 1.000 H
  H10C 0.665(2) 0.9792(19) 0.1656(15) 0.070(5) Uiso . . 1.000 H
  H7 0.456(3) 0.627(2) 0.3339(18) 0.084(6) Uiso . . 1.000 H
  H16 0.214(2) 0.4824(17) -0.0032(13) 0.061(5) Uiso . . 1.000 H
  H17 0.699(2) 0.5659(17) 0.1654(14) 0.057(4) Uiso . . 1.000 H
  H12 0.2941(19) 0.9110(15) 0.6108(12) 0.050(4) Uiso . . 1.000 H
  H13 0.5841(19) 0.8611(16) 0.3918(13) 0.052(4) Uiso . . 1.000 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 0.0658(6) 0.0602(6) 0.0249(4) 0.0167(5) 0.0144(4) 0.0045(4)
  O2 0.0536(5) 0.0474(5) 0.0341(4) 0.0064(4) -0.0054(4) 0.0164(4)
  O3 0.0479(5) 0.0623(6) 0.0454(5) 0.0304(5) 0.0053(4) 0.0136(4)
  N1 0.0435(5) 0.0234(4) 0.0325(4) 0.0064(4) 0.0042(4) 0.0023(3)
  N2 0.0859(9) 0.0355(6) 0.0567(7) 0.0108(6) 0.0429(7) 0.0092(5)
  N3 0.0497(5) 0.0264(4) 0.0329(4) 0.0097(4) 0.0149(4) 0.0030(3)
  N4 0.0632(7) 0.0246(4) 0.0318(5) 0.0109(4) 0.0157(4) 0.0044(4)
  C1' 0.0372(5) 0.0281(4) 0.0242(4) 0.0104(4) 0.0053(4) 0.0030(3)
  C2 0.0422(6) 0.0288(5) 0.0358(5) 0.0087(4) 0.0114(4) 0.0040(4)
  C2' 0.0394(6) 0.0359(5) 0.0273(5) 0.0130(4) 0.0088(4) 0.0031(4)
  C3' 0.0452(6) 0.0339(5) 0.0240(4) 0.0057(4) 0.0084(4) 0.0038(4)
  C4 0.0372(5) 0.0263(4) 0.0261(4) 0.0092(4) 0.0042(4) 0.0027(3)
  C4' 0.0429(6) 0.0338(5) 0.0265(5) 0.0059(4) 0.0000(4) 0.0094(4)
  C5 0.0352(5) 0.0291(4) 0.0223(4) 0.0121(4) 0.0011(4) 0.0018(3)
  C5' 0.0372(5) 0.0335(5) 0.0337(5) 0.0124(4) 0.0035(4) 0.0074(4)
  C6 0.0430(6) 0.0278(5) 0.0264(4) 0.0122(4) 0.0002(4) -0.0011(4)
  C6' 0.0397(5) 0.0353(5) 0.0262(4) 0.0151(4) 0.0059(4) 0.0036(4)
  C7 0.0381(5) 0.0382(5) 0.0272(5) 0.0179(5) 0.0060(4) 0.0043(4)
  C8 0.0701(10) 0.0680(10) 0.0420(7) 0.0178(8) 0.0255(7) -0.0056(7)
  C9 0.0531(8) 0.0599(9) 0.0433(7) 0.0091(7) -0.0093(6) 0.0067(7)
  C10 0.0532(8) 0.0615(9) 0.0598(8) 0.0328(7) 0.0175(7) 0.0168(7)
  O6 0.0544(6) 0.0666(7) 0.0680(7) 0.0153(5) 0.0290(5) -0.0085(5)
  O7 0.0623(6) 0.0695(7) 0.0452(5) 0.0069(5) 0.0220(5) -0.0099(5)
  C15 0.0431(6) 0.0291(5) 0.0418(6) 0.0079(4) 0.0170(5) 0.0028(4)
  C16 0.0382(6) 0.0446(6) 0.0486(7) 0.0107(5) 0.0146(5) 0.0020(5)
  C17 0.0412(6) 0.0451(6) 0.0418(6) 0.0086(5) 0.0089(5) -0.0006(5)
  C18 0.0529(7) 0.0306(5) 0.0475(7) 0.0112(5) 0.0218(6) 0.0031(5)
  O4 0.0794(7) 0.0289(4) 0.0510(5) 0.0093(4) 0.0355(5) -0.0005(4)
  O5 0.0549(5) 0.0273(4) 0.0410(4) 0.0038(3) 0.0215(4) 0.0022(3)
  C11 0.0340(5) 0.0246(4) 0.0257(4) 0.0048(4) 0.0029(4) 0.0019(3)
  C12 0.0414(6) 0.0291(5) 0.0362(5) 0.0053(4) 0.0150(5) 0.0030(4)
  C13 0.0446(6) 0.0275(5) 0.0375(5) 0.0078(4) 0.0154(5) 0.0008(4)
  C14 0.0380(5) 0.0265(4) 0.0251(4) 0.0063(4) 0.0040(4) 0.0006(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
  O1 C3' . . 1.3694(14) yes
  O1 C8 . . 1.423(2) yes
  O2 C4' . . 1.3873(15) yes
  O2 C9 . . 1.419(2) yes
  O3 C5' . . 1.3640(17) yes
  O3 C10 . . 1.4174(19) yes
  O6 C18 . . 1.202(2) yes
  O7 C18 . . 1.3196(18) yes
  O7 H7 . . 0.94(2) no
  O4 C14 . . 1.2601(15) yes
  O5 C14 . . 1.2420(15) yes
  N1 C6 . . 1.3552(15) yes
  N1 C2 . . 1.3549(15) yes
  N2 C2 . . 1.3256(19) yes
  N3 C2 . . 1.3342(15) yes
  N3 C4 . . 1.3425(15) yes
  N4 C4 . . 1.3380(14) yes
  N1 H1 . . 0.992(17) no
  N2 H2B . . 0.870(19) no
  N2 H2A . . 0.909(19) no
  N4 H4A . . 0.852(17) no
  N4 H4B . . 0.884(16) no
  C1' C6' . . 1.3847(18) no
  C1' C2' . . 1.3917(16) no
  C1' C7 . . 1.5210(16) no
  C2' C3' . . 1.3963(16) no
  C3' C4' . . 1.3859(19) no
  C4 C5 . . 1.4337(15) no
  C4' C5' . . 1.3897(16) no
  C5 C7 . . 1.4998(15) no
  C5 C6 . . 1.3524(15) no
  C5' C6' . . 1.3966(16) no
  C2' H2 . . 0.943(16) no
  C6 H6 . . 0.958(14) no
  C6' H6' . . 1.000(15) no
  C7 H7B . . 1.056(17) no
  C7 H7A . . 0.974(17) no
  C8 H8A . . 1.030(19) no
  C8 H8C . . 1.02(2) no
  C8 H8B . . 0.91(2) no
  C9 H9C . . 0.94(2) no
  C9 H9B . . 0.93(2) no
  C9 H9A . . 0.98(3) no
  C10 H10B . . 1.001(19) no
  C10 H10A . . 0.93(3) no
  C10 H10C . . 1.023(19) no
  C15 C18 . . 1.4929(19) no
  C15 C17 . . 1.385(2) no
  C15 C16 . . 1.3925(19) no
  C16 C17 . 2_665 1.380(2) no
  C16 H16 . . 0.969(18) no
  C17 H17 . . 1.023(18) no
  C11 C12 . . 1.3928(16) no
  C11 C13 . . 1.3865(17) no
  C11 C14 . . 1.5125(14) no
  C12 C13 . 2_676 1.3913(16) no
  C12 H12 . . 0.961(16) no
  C13 H13 . . 0.965(17) no