data_2200672 _journal_name_full 'Acta Crystallographica, Section E' _journal_year 2001 _journal_volume 57 _journal_page_first o1179 _journal_page_last o1182 _publ_section_title ; Hydrogen bonding patterns in trimethoprim sulfate trihydrate [trimethoprim = 2,4-diamino-5-(3,4,5-methoxybenzyl)pyrimidine]. ; loop_ _publ_author_name 'Thomas Muthiah, Packianathan' 'Umadevi, Balakrishnan' 'Stanley, Nithianantham' 'Shui, Xiugi' 'Eggleston, Drake S' _chemical_name_common 'Trimethoprim sulfate trihydrate' _chemical_formula_moiety '2C14 H19 N4 O3 1+ , S O4 1- , 3H2 O' _chemical_formula_sum 'C28 H44 N8 O13 S' _chemical_formula_weight 732.78 _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/c' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,1/2+y,1/2-z -x,-y,-z x,1/2-y,1/2+z _cell_length_a 7.2290(10) _cell_length_b 23.2420(10) _cell_length_c 20.3730(10) _cell_angle_alpha 90 _cell_angle_beta 98.590(10) _cell_angle_gamma 90 _cell_volume 3384.6(5) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _exptl_crystal_density_diffrn 1.438 _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 O3 .2086(2) .25126(6) .31273(6) .0388(5) Uani . . 1.000 O O4 .15474(18) .16421(5) .39394(6) .0310(4) Uani . . 1.000 O O5 .12160(19) .18298(5) .52203(6) .0317(4) Uani . . 1.000 O N1 -.1165(2) .44433(7) .60943(8) .0269(5) Uani . . 1.000 N N2 -.4164(2) .48104(8) .59187(9) .0317(5) Uani . . 1.000 N N3 -.2813(2) .45343(6) .50171(7) .0243(4) Uani . . 1.000 N N4 -.1480(3) .42782(7) .41176(8) .0294(5) Uani . . 1.000 N C2 -.2703(3) .45939(7) .56726(8) .0244(5) Uani . . 1.000 C C4 -.1318(2) .43258(7) .47728(8) .0231(5) Uani . . 1.000 C C5 .0373(2) .41617(7) .51969(8) .0239(5) Uani . . 1.000 C C6 .0351(3) .42325(8) .58539(9) .0269(5) Uani . . 1.000 C C7 .2069(3) .39311(8) .49325(10) .0280(6) Uani . . 1.000 C C8 .1871(2) .33190(8) .46688(9) .0241(5) Uani . . 1.000 C C9 .2058(2) .32122(8) .40121(9) .0262(5) Uani . . 1.000 C C10 .1928(2) .26531(8) .37706(8) .0267(5) Uani . . 1.000 C C11 .1632(2) .21970(7) .41838(9) .0249(5) Uani . . 1.000 C C12 .1480(2) .23072(8) .48494(9) .0250(5) Uani . . 1.000 C C13 .1592(2) .28677(8) .50898(9) .0248(5) Uani . . 1.000 C C14 .2066(4) .29777(11) .26603(11) .0447(8) Uani . . 1.000 C C15 -.0336(3) .14312(10) .37733(13) .0415(7) Uani . . 1.000 C C16 .1226(3) .19124(10) .59154(10) .0324(6) Uani . . 1.000 C O3A .7323(2) .25401(6) .27892(6) .0419(5) Uani . . 1.000 O O4A .73218(18) .17080(5) .18802(6) .0320(4) Uani . . 1.000 O O5A .6587(2) .19370(6) .05887(6) .0350(4) Uani . . 1.000 O N1A .4728(2) .42514(7) -.07646(7) .0262(5) Uani . . 1.000 N N2A .6395(3) .46965(8) -.14905(8) .0328(5) Uani . . 1.000 N N3A .7644(2) .46739(6) -.03793(7) .0247(4) Uani . . 1.000 N N4A .8883(2) .46221(8) .07139(8) .0326(5) Uani . . 1.000 N C2A .6277(2) .45456(7) -.08727(8) .0237(5) Uani . . 1.000 C C4A .7473(2) .44981(7) .02405(8) .0230(5) Uani . . 1.000 C C5A .5838(2) .41962(7) .03831(8) .0223(5) Uani . . 1.000 C C6A .4510(3) .40909(7) -.01403(9) .0248(5) Uani . . 1.000 C C7A .5570(3) .40095(8) .10692(9) .0251(5) Uani . . 1.000 C C8A .6161(2) .33949(7) .12627(8) .0226(5) Uani . . 1.000 C C9A .6548(3) .32691(8) .19363(9) .0281(6) Uani . . 1.000 C C10A .6911(3) .27082(8) .21422(8) .0281(5) Uani . . 1.000 C C11A .6890(2) .22668(8) .16779(9) .0258(5) Uani . . 1.000 C C12A .6538(2) .23953(8) .10047(8) .0240(5) Uani . . 1.000 C C13A .6173(2) .29617(8) .07973(8) .0234(5) Uani . . 1.000 C C14A .7351(4) .29752(12) .32819(10) .0469(8) Uani . . 1.000 C C15A .5799(4) .14029(11) .20911(14) .0456(8) Uani . . 1.000 C C16A .6522(3) .20627(9) -.00964(9) .0317(6) Uani . . 1.000 C S1 .06550(6) .46246(2) .25336(2) .02430(10) Uani . . 1.000 S O6 .1140(2) .52387(6) .26534(6) .0347(4) Uani . . 1.000 O O7 .0962(2) .43137(6) .31571(7) .0426(5) Uani . . 1.000 O O8 -.1317(2) .45910(7) .22252(8) .0479(5) Uani . . 1.000 O O9 .1836(2) .43906(6) .20703(7) .0447(5) Uani . . 1.000 O O1' .2813(2) .06925(8) .29492(8) .0446(5) Uani . . 1.000 O O2' .5571(3) .45244(8) .29707(8) .0487(6) Uani . . 1.000 O O3' .1171(2) .15968(7) .22232(8) .0468(5) Uani . . 1.000 O H1 -.114(3) .4514(10) .6511(12) .047(7) Uiso . . 1.000 H H2 .147(3) .2944(8) .5538(10) .024(5) Uiso . . 1.000 H H6 .021(3) .2149(9) .5999(10) .037(6) Uiso . . 1.000 H H10 .142(3) .4145(9) .6172(10) .032(5) Uiso . . 1.000 H H11 .242(3) .2074(9) .6132(10) .038(6) Uiso . . 1.000 H H12 .312(3) .3934(8) .5302(10) .030(5) Uiso . . 1.000 H H14 .236(3) .4178(9) .4593(10) .029(5) Uiso . . 1.000 H H15 .225(3) .3521(9) .3736(10) .030(5) Uiso . . 1.000 H H21 -.252(4) .4383(10) .3872(12) .045(7) Uiso . . 1.000 H H24 -.025(3) .1062(12) .3600(12) .053(7) Uiso . . 1.000 H H26 .108(3) .1545(10) .6097(11) .041(6) Uiso . . 1.000 H H30 -.052(3) .4219(10) .3905(12) .046(7) Uiso . . 1.000 H H32 -.096(4) .1425(12) .4169(14) .067(8) Uiso . . 1.000 H H33 -.101(3) .1687(11) .3447(12) .050(7) Uiso . . 1.000 H H34 .087(4) .3192(11) .2638(12) .057(7) Uiso . . 1.000 H H35 .317(4) .3246(13) .2777(13) .069(8) Uiso . . 1.000 H H39 .219(4) .2776(14) .2271(15) .078(9) Uiso . . 1.000 H H40 -.502(3) .4976(10) .5649(12) .041(6) Uiso . . 1.000 H H41 -.405(3) .4915(10) .6324(12) .042(6) Uiso . . 1.000 H H3 .623(3) .4259(8) .1399(10) .026(5) Uiso . . 1.000 H H4 .424(3) .4034(9) .1095(10) .032(5) Uiso . . 1.000 H H5 .654(3) .1703(10) -.0320(11) .040(6) Uiso . . 1.000 H H7 .336(3) .3901(9) -.0112(9) .028(5) Uiso . . 1.000 H H8 .551(3) .4600(8) -.1774(10) .023(5) Uiso . . 1.000 H H13 .651(3) .3576(9) .2248(10) .032(5) Uiso . . 1.000 H H17 .758(3) .2311(10) -.0165(11) .046(6) Uiso . . 1.000 H H18 .627(3) .1044(12) .2217(12) .052(7) Uiso . . 1.000 H H19 .535(3) .2244(9) -.0269(10) .034(5) Uiso . . 1.000 H H20 .542(4) .1595(13) .2462(14) .071(9) Uiso . . 1.000 H H22 .989(3) .4805(10) .0587(11) .042(6) Uiso . . 1.000 H H23 .726(4) .4948(11) -.1610(12) .056(7) Uiso . . 1.000 H H27 .885(3) .4524(10) .1137(12) .041(6) Uiso . . 1.000 H H28 .617(4) .3126(11) .3286(12) .054(7) Uiso . . 1.000 H H29 .776(3) .2781(10) .3695(13) .051(7) Uiso . . 1.000 H H31 .590(3) .3050(8) .0338(10) .027(5) Uiso . . 1.000 H H36 .474(4) .1388(12) .1740(15) .073(9) Uiso . . 1.000 H H37 .391(3) .4184(10) -.1098(12) .043(6) Uiso . . 1.000 H H38 .830(4) .3295(13) .3197(14) .072(9) Uiso . . 1.000 H H1' .230(3) .1004(9) .2760(9) .016(4) Uiso . . 1.000 H H2' .207(4) .0376(14) .2864(14) .075(9) Uiso . . 1.000 H H3' .467(4) .4452(11) .2783(13) .046(8) Uiso . . 1.000 H H4' .639(4) .4542(12) .2687(15) .070(9) Uiso . . 1.000 H H5' .143(5) .1885(16) .2604(18) .103(12) Uiso . . 1.000 H H6' -.030(7) .158(2) .217(2) .169(19) 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 O3 .0575(9) .0392(8) .0199(7) .0030(7) .0063(6) -.0029(6) O4 .0333(7) .0257(7) .0320(7) .0040(5) -.0015(5) -.0060(5) O5 .0431(8) .0262(7) .0266(7) .0013(6) .0078(6) .0039(5) N1 .0348(9) .0278(8) .0172(8) .0011(7) .0009(6) -.0027(6) N2 .0359(9) .0393(10) .0201(8) .0059(8) .0051(7) -.0042(7) N3 .0289(8) .0240(8) .0195(7) .0007(6) .0021(6) -.0018(6) N4 .0316(9) .0370(9) .0196(8) .0052(7) .0036(7) -.0017(7) C2 .0319(9) .0201(8) .0210(8) -.0030(7) .0032(7) -.0007(7) C4 .0301(9) .0172(8) .0218(9) -.0030(7) .0031(7) -.0009(7) C5 .0276(9) .0177(8) .0258(9) -.0024(7) .0017(7) -.0019(7) C6 .0314(10) .0220(9) .0253(9) .0004(7) -.0028(8) -.0005(7) C7 .0261(9) .0264(10) .0307(10) -.0025(7) .0020(8) -.0017(8) C8 .0187(8) .0271(9) .0257(9) .0026(7) .0003(7) -.0009(7) C9 .0257(9) .0275(10) .0245(9) .0012(7) .0012(7) .0051(8) C10 .0262(9) .0349(10) .0182(8) .0039(8) .0004(7) -.0003(7) C11 .0223(8) .0242(9) .0270(9) .0043(7) -.0003(7) -.0043(7) C12 .0226(9) .0274(9) .0248(9) .0034(7) .0031(7) .0036(7) C13 .0236(9) .0289(10) .0221(9) .0032(7) .0041(7) -.0024(7) C14 .0615(16) .0503(14) .0232(11) -.0020(12) .0089(10) .0047(10) C15 .0429(12) .0337(12) .0478(13) -.0099(10) .0061(11) -.0068(11) C16 .0335(11) .0377(11) .0276(10) .0047(9) .0098(8) .0055(9) O3A .0645(10) .0408(8) .0181(7) .0053(7) -.0012(6) .0052(6) O4A .0336(7) .0297(7) .0330(7) .0064(6) .0058(6) .0093(6) O5A .0539(9) .0268(7) .0240(7) .0087(6) .0051(6) -.0016(5) N1A .0273(8) .0286(8) .0208(8) -.0032(6) -.0026(6) .0009(6) N2A .0366(10) .0387(10) .0226(8) -.0048(8) .0029(7) .0046(7) N3A .0246(7) .0256(8) .0239(8) -.0017(6) .0036(6) -.0006(6) N4A .0297(9) .0412(10) .0253(9) -.0093(7) -.0008(7) .0009(7) C2A .0279(9) .0200(8) .0237(9) .0024(7) .0051(7) .0016(7) C4A .0252(9) .0193(8) .0243(9) .0014(7) .0027(7) -.0012(7) C5A .0259(9) .0179(8) .0228(9) -.0003(7) .0031(7) .0001(7) C6A .0272(9) .0215(9) .0257(9) -.0027(7) .0035(7) .0016(7) C7A .0295(10) .0240(9) .0221(9) -.0025(8) .0045(7) -.0010(7) C8A .0190(8) .0266(9) .0224(9) -.0019(7) .0039(6) .0023(7) C9A .0330(10) .0300(10) .0212(9) -.0019(8) .0034(7) -.0030(8) C10A .0295(9) .0358(10) .0183(9) .0002(8) .0012(7) .0043(7) C11A .0232(9) .0275(9) .0265(9) .0024(7) .0028(7) .0058(7) C12A .0218(8) .0274(9) .0227(9) .0008(7) .0034(7) -.0008(7) C13A .0230(9) .0279(9) .0190(9) -.0003(7) .0022(7) .0025(7) C14A .0536(14) .0671(16) .0175(10) .0191(13) -.0028(10) -.0026(10) C15A .0494(14) .0316(12) .0571(15) -.0006(10) .0121(12) .0112(11) C16A .0352(11) .0367(11) .0226(9) .0064(9) .0028(8) -.0045(8) S1 .0301(2) .0267(2) .0162(2) -.0033(2) .0037(2) .0009(2) O6 .0503(8) .0314(7) .0229(7) -.0094(6) .0068(6) -.0036(5) O7 .0601(10) .0434(9) .0257(7) .0091(7) .0106(7) .0121(6) O8 .0363(8) .0499(9) .0532(9) -.0071(7) -.0074(7) -.0013(7) O9 .0654(10) .0383(8) .0364(8) -.0052(7) .0275(7) -.0052(6) O1' .0429(9) .0411(9) .0443(9) -.0021(8) -.0111(7) -.0043(7) O2' .0396(9) .0735(12) .0321(8) .0057(9) .0026(8) -.0048(8) O3' .0428(9) .0461(9) .0493(9) .0063(7) .0000(7) -.0085(7) 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 S1 O9 . . 1.4684(15) yes S1 O6 . . 1.4812(15) yes S1 O7 . . 1.4494(15) yes S1 O8 . . 1.4716(16) yes O3 C14 . . 1.439(3) yes O3 C10 . . 1.372(2) yes O4 C11 . . 1.381(2) yes O4 C15 . . 1.439(3) yes O5 C12 . . 1.372(2) yes O5 C16 . . 1.428(2) yes O3A C14A . . 1.423(3) yes O3A C10A . . 1.364(2) yes O4A C15A . . 1.428(3) yes O4A C11A . . 1.384(2) yes O5A C16A . . 1.420(2) yes O5A C12A . . 1.365(2) yes O1' H2' . . .91(3) no O1' H1' . . .88(2) no O2' H3' . . .72(3) no O2' H4' . . .89(3) no N1 C6 . . 1.357(3) yes N1 C2 . . 1.346(2) yes N2 C2 . . 1.334(3) yes N3 C2 . . 1.333(2) yes N3 C4 . . 1.346(2) yes N4 C4 . . 1.327(2) yes N1 H1 . . .86(2) no N2 H40 . . .86(2) no N2 H41 . . .85(2) no O3' H6' . . 1.05(5) no O3' H5' . . 1.02(4) no N4 H30 . . .88(2) no N4 H21 . . .87(3) no N1A C2A . . 1.358(2) yes N1A C6A . . 1.357(2) yes N2A C2A . . 1.322(2) yes N3A C4A . . 1.350(2) yes N3A C2A . . 1.334(2) yes N4A C4A . . 1.326(2) yes N1A H37 . . .85(2) no N2A H23 . . .92(3) no N2A H8 . . .83(2) no N4A H22 . . .91(2) no N4A H27 . . .90(2) no C4 C5 . . 1.439(2) no C5 C7 . . 1.509(3) no C5 C6 . . 1.351(2) no C7 C8 . . 1.520(3) no C8 C9 . . 1.387(3) no C8 C13 . . 1.389(3) no C9 C10 . . 1.388(3) no C10 C11 . . 1.390(2) no C11 C12 . . 1.400(3) no C12 C13 . . 1.390(3) no C6 H10 . . .95(2) no C7 H12 . . .99(2) no C7 H14 . . .95(2) no C9 H15 . . .93(2) no C13 H2 . . .95(2) no C14 H35 . . 1.01(3) no C14 H34 . . .99(3) no C14 H39 . . .94(3) no C15 H33 . . .97(2) no C15 H32 . . .98(3) no C15 H24 . . .93(3) no C16 H26 . . .94(2) no C16 H6 . . .95(2) no C16 H11 . . .98(2) no C4A C5A . . 1.441(2) no C5A C6A . . 1.346(3) no C5A C7A . . 1.504(2) no C7A C8A . . 1.526(2) no C8A C9A . . 1.390(2) no C8A C13A . . 1.384(2) no C9A C10A . . 1.383(3) no C10A C11A . . 1.394(3) no C11A C12A . . 1.390(2) no C12A C13A . . 1.396(3) no C6A H7 . . .95(2) no C7A H4 . . .97(2) no C7A H3 . . .96(2) no C9A H13 . . .96(2) no C13A H31 . . .95(2) no C14A H28 . . .92(3) no C14A H38 . . 1.04(3) no C14A H29 . . .96(3) no C15A H36 . . .97(3) no C15A H20 . . .95(3) no C15A H18 . . .92(3) no C16A H5 . . .95(2) no C16A H17 . . .98(2) no C16A H19 . . .96(2) no