#------------------------------------------------------------------------------
#$Date: 2011-09-17 23:27:16 +0300 (Sat, 17 Sep 2011) $
#$Revision: 26029 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/2200671.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_2200671
loop_
_publ_author_name
'Justin Robert, Jebamony'
'Baskar Raj, Savarimuthu'
'Thomas Muthiah, Packianathan'
_publ_section_title
;
N--H...O and O--H..O hydrogen bonds in crystal engineering:
trimethoprim hydrogen glutarate
;
_journal_name_full               'Acta Crystallographica, Section E'
_journal_page_first              o1206
_journal_page_last               o1208
_journal_volume                  57
_journal_year                    2001
_chemical_formula_iupac          'C14 H19 N4 O3 1+, C5 H7 O4 1-'
_chemical_formula_moiety         'C14 H19 N4 O3 1+, C5 H7 O4 1-'
_chemical_formula_sum            'C19 H26 N4 O7'
_chemical_formula_weight         422.44
_chemical_name_common            'trimethoprim glutarate'
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_cell_angle_alpha                84.430(3)
_cell_angle_beta                 94.900(3)
_cell_angle_gamma                104.590(3)
_cell_formula_units_Z            2
_cell_length_a                   12.017(2)
_cell_length_b                   10.090(3)
_cell_length_c                   8.804(4)
_cell_measurement_temperature    293(2)
_cell_volume                     1026.1(6)
_diffrn_ambient_temperature      290
_exptl_crystal_density_diffrn    1.367
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_database_code               2200671
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
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 .0623(9) .0730(9) .0425(7) .0242(7) -.0178(6) -.0137(6)
O2 .0463(8) .0617(8) .0632(9) .0194(6) -.0184(6) -.0057(7)
O3 .0579(8) .0791(10) .0521(8) .0335(7) -.0016(7) -.0095(7)
N1 .0559(10) .0568(9) .0362(8) .0191(8) -.0087(7) -.0075(7)
N2 .0778(12) .0601(10) .0335(8) .0206(9) -.0137(8) -.0041(7)
N3 .0618(10) .0559(9) .0368(8) .0224(8) -.0123(7) -.0060(7)
N4 .0913(14) .0665(11) .0453(9) .0185(10) -.0269(9) -.0106(8)
C2 .0529(10) .0565(11) .0346(9) .0259(9) -.0067(7) -.0062(8)
C4 .0531(10) .0624(11) .0363(9) .0256(9) -.0111(8) -.0091(8)
C5 .0447(10) .0671(12) .0344(9) .0264(9) -.0048(7) -.0015(8)
C6 .0487(10) .0601(11) .0380(9) .0215(9) -.0031(8) .0009(8)
C7 .0475(11) .0916(16) .0351(10) .0294(10) -.0042(8) .0037(9)
C8 .0441(9) .0540(10) .0318(8) .0150(8) -.0049(7) .0054(7)
C9 .0473(10) .0534(10) .0363(9) .0182(8) -.0022(7) .0003(7)
C10 .0480(10) .0441(9) .0370(9) .0099(8) -.0096(7) -.0002(7)
C11 .0411(9) .0447(9) .0460(10) .0120(8) -.0097(8) .0014(8)
C12 .0455(10) .0442(9) .0441(10) .0145(8) .0001(8) .0013(7)
C13 .0473(10) .0536(10) .0337(9) .0154(8) -.0054(7) -.0002(7)
C14 .0773(15) .0705(14) .0450(11) .0219(12) -.0100(10) -.0156(10)
C15 .0932(19) .0690(16) .105(2) .0394(14) -.0495(17) -.0099(14)
C16 .0840(17) .0896(17) .0559(13) .0452(14) .0034(12) -.0126(12)
O4 .0981(13) .0656(10) .0387(7) -.0026(9) -.0159(8) -.0004(7)
O5 .0904(12) .0756(10) .0283(7) .0067(8) -.0054(7) -.0004(6)
O6 .0981(13) .1065(14) .0543(9) .0601(12) -.0022(9) -.0001(9)
O7 .1041(13) .0958(13) .0474(9) .0590(11) .0186(9) .0171(8)
C17 .0562(11) .0426(9) .0386(9) .0085(8) -.0055(8) -.0076(7)
C18 .0796(15) .0553(12) .0394(10) .0083(10) .0014(10) -.0017(8)
C19 .0742(14) .0598(12) .0357(10) .0023(10) -.0059(9) -.0030(8)
C20 .0698(14) .0612(12) .0377(10) .0083(10) -.0001(9) -.0026(9)
C21 .0522(11) .0654(12) .0319(9) .0075(9) .0003(8) -.0012(8)
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 .45141(13) .87527(15) .73650(15) .0585(5) Uani . . 1.000 O
O2 .59069(12) .78210(15) .57704(17) .0572(5) Uani . . 1.000 O
O3 .52998(13) .71564(16) .29046(16) .0600(5) Uani . . 1.000 O
N1 .05252(14) .82591(17) -.10391(17) .0491(5) Uani . . 1.000 N
N2 .06864(17) .98838(19) -.31074(18) .0575(6) Uani . . 1.000 N
N3 .15813(15) 1.05315(17) -.07878(18) .0508(5) Uani . . 1.000 N
N4 .24980(19) 1.1136(2) .1481(2) .0693(7) Uani . . 1.000 N
C2 .09384(17) .9571(2) -.1627(2) .0461(6) Uani . . 1.000 C
C4 .18378(17) 1.0157(2) .0689(2) .0490(6) Uani . . 1.000 C
C5 .14042(16) .8791(2) .1401(2) .0471(6) Uani . . 1.000 C
C6 .07496(17) .7889(2) .0470(2) .0481(6) Uani . . 1.000 C
C7 .15670(17) .8417(3) .3090(2) .0568(7) Uani . . 1.000 C
C8 .27701(15) .83263(19) .37225(19) .0438(5) Uani . . 1.000 C
C9 .30932(16) .86674(19) .5205(2) .0452(6) Uani . . 1.000 C
C10 .41372(16) .84784(18) .5896(2) .0442(5) Uani . . 1.000 C
C11 .48561(15) .79685(18) .5096(2) .0447(5) Uani . . 1.000 C
C12 .45284(16) .76436(19) .3595(2) .0445(6) Uani . . 1.000 C
C13 .34798(16) .78229(19) .2912(2) .0450(6) Uani . . 1.000 C
C14 .3789(2) .9274(3) .8200(2) .0637(8) Uani . . 1.000 C
C15 .5871(3) .6471(3) .6435(4) .0887(11) Uani . . 1.000 C
C16 .5029(2) .6836(3) .1364(3) .0718(9) Uani . . 1.000 C
O4 .07782(16) .22219(17) .46913(16) .0730(6) Uani . . 1.000 O
O5 .08143(15) .37575(17) .27020(15) .0680(6) Uani . . 1.000 O
O6 .27767(17) .4052(2) 1.00442(19) .0808(7) Uani . . 1.000 O
O7 .14593(17) .5178(2) 1.01426(18) .0769(7) Uani . . 1.000 O
C17 .21973(17) .47756(18) .9423(2) .0467(6) Uani . . 1.000 C
C18 .2212(2) .5289(2) .7757(2) .0599(7) Uani . . 1.000 C
C19 .1775(2) .4110(2) .6763(2) .0597(7) Uani . . 1.000 C
C20 .1615(2) .4566(2) .5084(2) .0579(7) Uani . . 1.000 C
C21 .10397(17) .3416(2) .4102(2) .0514(6) Uani . . 1.000 C
H1 .01188 .76561 -.16215 .0589 Uiso . . 1.000 H
H2A .09426 1.07055 -.35075 .0690 Uiso . . 1.000 H
H2B .02682 .92626 -.36587 .0690 Uiso . . 1.000 H
H4A .27354 1.19502 .10514 .0831 Uiso . . 1.000 H
H4B .26913 1.09607 .24285 .0831 Uiso . . 1.000 H
H6 .04414 .69920 .08567 .0578 Uiso . . 1.000 H
H7A .10386 .75354 .33305 .0682 Uiso . . 1.000 H
H7B .13408 .90891 .36339 .0682 Uiso . . 1.000 H
H9 .26158 .90228 .57429 .0542 Uiso . . 1.000 H
H13 .32619 .76023 .19099 .0540 Uiso . . 1.000 H
H14A .36428 1.00926 .76587 .0955 Uiso . . 1.000 H
H14B .41563 .94859 .91885 .0955 Uiso . . 1.000 H
H14C .30728 .85986 .83196 .0955 Uiso . . 1.000 H
H15A .53305 .62400 .72187 .1328 Uiso . . 1.000 H
H15B .66225 .64316 .68745 .1328 Uiso . . 1.000 H
H15C .56371 .58310 .56618 .1328 Uiso . . 1.000 H
H16A .43188 .61417 .12954 .1077 Uiso . . 1.000 H
H16B .56356 .65035 .10126 .1077 Uiso . . 1.000 H
H16C .49499 .76465 .07415 .1077 Uiso . . 1.000 H
H7 .13895 .47592 1.09892 .1155 Uiso . . 1.000 H
H18A .17318 .59359 .75535 .0719 Uiso . . 1.000 H
H18B .29921 .57640 .75171 .0719 Uiso . . 1.000 H
H19A .10431 .35621 .71116 .0717 Uiso . . 1.000 H
H19B .23141 .35296 .68798 .0717 Uiso . . 1.000 H
H20A .11585 .52405 .49846 .0695 Uiso . . 1.000 H
H20B .23641 .50118 .47063 .0695 Uiso . . 1.000 H
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 C10 . . 1.364(2) yes
O1 C14 . . 1.411(3) yes
O2 C11 . . 1.385(2) yes
O2 C15 . . 1.421(3) yes
O3 C12 . . 1.362(3) yes
O3 C16 . . 1.417(3) yes
O4 C21 . . 1.239(3) yes
O5 C21 . . 1.272(2) yes
O6 C17 . . 1.196(3) yes
O7 C17 . . 1.296(3) yes
O7 H7 . . .8203 no
N1 C6 . . 1.368(2) yes
N1 C2 . . 1.359(3) yes
N2 C2 . . 1.338(2) yes
N3 C2 . . 1.321(3) yes
N3 C4 . . 1.350(2) yes
N4 C4 . . 1.317(3) yes
N1 H1 . . .8600 no
N2 H2B . . .8601 no
N2 H2A . . .8599 no
N4 H4B . . .8603 no
N4 H4A . . .8599 no
C4 C5 . . 1.446(3) no
C5 C7 . . 1.507(3) no
C5 C6 . . 1.339(3) no
C7 C8 . . 1.526(3) no
C8 C9 . . 1.381(3) no
C8 C13 . . 1.374(3) no
C9 C10 . . 1.396(3) no
C10 C11 . . 1.380(3) no
C11 C12 . . 1.392(3) no
C12 C13 . . 1.395(3) no
C6 H6 . . .9301 no
C7 H7B . . .9702 no
C7 H7A . . .9701 no
C9 H9 . . .9301 no
C13 H13 . . .9305 no
C14 H14B . . .9596 no
C14 H14A . . .9605 no
C14 H14C . . .9604 no
C15 H15B . . .9603 no
C15 H15C . . .9595 no
C15 H15A . . .9599 no
C16 H16B . . .9600 no
C16 H16A . . .9597 no
C16 H16C . . .9599 no
C17 C18 . . 1.507(3) no
C18 C19 . . 1.505(3) no
C19 C20 . . 1.516(3) no
C20 C21 . . 1.503(3) no
C18 H18A . . .9698 no
C18 H18B . . .9700 no
C19 H19A . . .9704 no
C19 H19B . . .9702 no
C20 H20A . . .9696 no
C20 H20B . . .9702 no