data_7150192
_journal_name_full  'Organic & Biomolecular Chemistry'
_journal_year       2005
_publ_section_title
;
2,4-Dithiouracil: the reproducible H-bonded structural
motifs in the complexes with 18-membered crown ethers
;
loop_
_publ_author_name
'Marina Fonari'
'Gabriele Bocelli'
'Eduard V. Ganin'
'Yurii A. Simonov'
'Wen-Jwu Wang'
_chemical_name_common
;
1,4,7,10,13,16-hexaoxacyclooctadecane pyrimidine-2,4(1H,3H)-
dithione monohydrate
;
_chemical_melting_point  265
_chemical_formula_moiety  'C12 H24 O6, C4 H4 N2 S2, H2 O'
_chemical_formula_sum  'C16 H30 N2 O7 S2'
_chemical_formula_weight  426.54
_symmetry_cell_setting  monoclinic
_symmetry_space_group_name_H-M  'P 21/n'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
_cell_length_a  7.7070(15)
_cell_length_b  17.374(4)
_cell_length_c  16.622(3)
_cell_angle_alpha  90.00
_cell_angle_beta  92.17(3)
_cell_angle_gamma  90.00
_cell_volume  2224.1(8)
_cell_formula_units_Z  4
_cell_measurement_temperature  293(2)
_exptl_crystal_density_diffrn  1.274
_diffrn_ambient_temperature  293(2)
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
S1 S 0.83374(8) 0.39910(3) 0.34792(3) 0.05751(19) Uani 1 1 d . . .
S2 S 0.90385(9) 0.09654(3) 0.32263(3) 0.0611(2) Uani 1 1 d . . .
N1U N 0.85880(18) 0.24579(8) 0.34830(8) 0.0339(3) Uani 1 1 d D . .
H1U H 0.893(3) 0.2521(12) 0.3038(10) 0.051 Uiso 1 1 d D . .
N2U N 0.7549(2) 0.30024(10) 0.46245(9) 0.0410(4) Uani 1 1 d D . .
H2U H 0.721(3) 0.3391(10) 0.4874(13) 0.062 Uiso 1 1 d D . .
C1U C 0.8146(2) 0.31173(10) 0.38777(10) 0.0349(4) Uani 1 1 d . . .
C2U C 0.8470(2) 0.17167(10) 0.37762(10) 0.0362(4) Uani 1 1 d . . .
C3U C 0.7848(3) 0.16582(11) 0.45675(11) 0.0439(5) Uani 1 1 d . . .
H3U H 0.7749 0.1179 0.4811 0.053 Uiso 1 1 calc R . .
C4U C 0.7407(3) 0.22962(12) 0.49606(11) 0.0465(5) Uani 1 1 d . . .
H4U H 0.6992 0.2254 0.5477 0.056 Uiso 1 1 calc R . .
O1 O 0.9162(2) 0.32898(9) 0.64854(9) 0.0605(4) Uani 1 1 d . . .
C2 C 0.9858(4) 0.28521(18) 0.71391(19) 0.0942(10) Uani 1 1 d . . .
H2A H 0.9097 0.2891 0.7589 0.113 Uiso 1 1 calc R . .
H2B H 1.0981 0.3060 0.7309 0.113 Uiso 1 1 calc R . .
C3 C 1.0052(4) 0.20461(19) 0.6919(2) 0.0909(9) Uani 1 1 d . . .
H3A H 1.0577 0.2010 0.6400 0.109 Uiso 1 1 calc R . .
H3B H 1.0812 0.1791 0.7314 0.109 Uiso 1 1 calc R . .
O4 O 0.8400(2) 0.16735(9) 0.68838(10) 0.0670(5) Uani 1 1 d . . .
C5 C 0.8564(4) 0.08763(14) 0.67455(16) 0.0780(8) Uani 1 1 d . . .
H5A H 0.9269 0.0644 0.7176 0.094 Uiso 1 1 calc R . .
H5B H 0.9131 0.0789 0.6242 0.094 Uiso 1 1 calc R . .
C6 C 0.6823(4) 0.05225(14) 0.67100(15) 0.0821(9) Uani 1 1 d . . .
H6A H 0.6928 -0.0033 0.6688 0.099 Uiso 1 1 calc R . .
H6B H 0.6209 0.0656 0.7189 0.099 Uiso 1 1 calc R . .
O7 O 0.5880(2) 0.07928(9) 0.60152(10) 0.0662(5) Uani 1 1 d . . .
C8 C 0.4120(4) 0.05721(14) 0.6000(2) 0.0863(9) Uani 1 1 d . . .
H8A H 0.3571 0.0756 0.6479 0.104 Uiso 1 1 calc R . .
H8B H 0.4022 0.0016 0.5983 0.104 Uiso 1 1 calc R . .
C9 C 0.3265(4) 0.09157(18) 0.5270(2) 0.0979(11) Uani 1 1 d . . .
H9A H 0.3951 0.0810 0.4805 0.118 Uiso 1 1 calc R . .
H9B H 0.2127 0.0687 0.5177 0.118 Uiso 1 1 calc R . .
O10 O 0.3096(2) 0.17287(10) 0.53730(12) 0.0780(5) Uani 1 1 d . . .
C11 C 0.2823(4) 0.2163(2) 0.46502(18) 0.0954(10) Uani 1 1 d . . .
H11A H 0.1852 0.1951 0.4334 0.114 Uiso 1 1 calc R . .
H11B H 0.3848 0.2139 0.4330 0.114 Uiso 1 1 calc R . .
C12 C 0.2452(4) 0.2980(2) 0.4870(2) 0.0930(10) Uani 1 1 d . . .
H12A H 0.2258 0.3285 0.4386 0.112 Uiso 1 1 calc R . .
H12B H 0.1415 0.3004 0.5182 0.112 Uiso 1 1 calc R . .
O13 O 0.38787(19) 0.32708(9) 0.53231(11) 0.0661(5) Uani 1 1 d . . .
C14 C 0.3706(3) 0.40575(14) 0.5567(2) 0.0837(9) Uani 1 1 d . . .
H14A H 0.2652 0.4119 0.5862 0.100 Uiso 1 1 calc R . .
H14B H 0.3623 0.4387 0.5096 0.100 Uiso 1 1 calc R . .
C15 C 0.5207(4) 0.42821(14) 0.60773(16) 0.0713(7) Uani 1 1 d . . .
H15A H 0.5055 0.4802 0.6274 0.086 Uiso 1 1 calc R . .
H15B H 0.5323 0.3940 0.6537 0.086 Uiso 1 1 calc R . .
O16 O 0.67023(19) 0.42417(8) 0.56227(8) 0.0504(4) Uani 1 1 d . . .
C17 C 0.8272(3) 0.45128(13) 0.60243(16) 0.0694(7) Uani 1 1 d . . .
H17A H 0.8087 0.5038 0.6200 0.083 Uiso 1 1 calc R . .
H17B H 0.9185 0.4523 0.5639 0.083 Uiso 1 1 calc R . .
C18 C 0.8867(4) 0.40592(14) 0.67159(18) 0.0764(8) Uani 1 1 d . . .
H18A H 0.9933 0.4278 0.6945 0.092 Uiso 1 1 calc R . .
H18B H 0.8001 0.4073 0.7124 0.092 Uiso 1 1 calc R . .
O1W O 0.9930(2) 0.26086(9) 0.19317(9) 0.0629(5) Uani 1 1 d D . .
H1W H 0.940(3) 0.2604(16) 0.1481(13) 0.094 Uiso 1 1 d D . .
H2W H 1.090(3) 0.2827(16) 0.1953(16) 0.094 Uiso 1 1 d D . .
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
S1 0.0813(4) 0.0346(3) 0.0575(3) -0.0014(2) 0.0149(3) -0.0066(3)
S2 0.0913(5) 0.0369(3) 0.0569(3) -0.0051(2) 0.0257(3) 0.0062(3)
N1U 0.0379(8) 0.0348(8) 0.0295(7) -0.0014(6) 0.0064(6) -0.0032(6)
N2U 0.0429(9) 0.0442(9) 0.0365(8) -0.0087(7) 0.0086(7) 0.0010(7)
C1U 0.0305(9) 0.0388(10) 0.0354(9) -0.0058(7) 0.0004(7) -0.0037(7)
C2U 0.0339(9) 0.0387(10) 0.0362(9) -0.0014(8) 0.0026(7) -0.0023(7)
C3U 0.0503(11) 0.0435(11) 0.0386(10) 0.0071(8) 0.0090(8) -0.0014(9)
C4U 0.0507(12) 0.0574(12) 0.0323(9) 0.0013(9) 0.0123(8) -0.0039(10)
O1 0.0596(10) 0.0570(9) 0.0636(10) -0.0098(7) -0.0144(8) 0.0075(7)
C2 0.096(2) 0.095(2) 0.088(2) 0.0024(17) -0.0489(18) -0.0019(18)
C3 0.0668(18) 0.094(2) 0.109(2) 0.0230(19) -0.0285(16) 0.0174(16)
O4 0.0764(12) 0.0591(10) 0.0655(10) 0.0087(8) 0.0013(8) 0.0209(8)
C5 0.109(2) 0.0577(15) 0.0674(16) 0.0189(12) 0.0080(15) 0.0364(15)
C6 0.144(3) 0.0400(13) 0.0652(16) 0.0182(11) 0.0393(17) 0.0159(15)
O7 0.0815(12) 0.0468(9) 0.0725(11) 0.0103(8) 0.0314(9) -0.0040(8)
C8 0.092(2) 0.0408(13) 0.130(3) -0.0143(15) 0.0538(19) -0.0182(14)
C9 0.0645(18) 0.090(2) 0.141(3) -0.059(2) 0.0191(19) -0.0277(15)
O10 0.0727(12) 0.0756(12) 0.0865(13) -0.0209(10) 0.0122(10) -0.0076(9)
C11 0.0536(16) 0.152(3) 0.079(2) -0.015(2) -0.0237(14) -0.0222(18)
C12 0.0510(16) 0.118(3) 0.108(2) 0.029(2) -0.0218(15) 0.0029(16)
O13 0.0410(8) 0.0721(11) 0.0849(11) 0.0145(9) -0.0030(8) 0.0104(7)
C14 0.0548(15) 0.0578(16) 0.141(3) 0.0319(16) 0.0319(16) 0.0254(12)
C15 0.0859(19) 0.0490(13) 0.0819(17) -0.0025(12) 0.0406(15) 0.0075(12)
O16 0.0604(9) 0.0430(7) 0.0483(8) -0.0045(6) 0.0078(7) 0.0076(6)
C17 0.0787(17) 0.0482(13) 0.0805(17) -0.0141(12) -0.0059(14) -0.0126(12)
C18 0.0820(19) 0.0595(16) 0.0860(19) -0.0250(14) -0.0196(15) -0.0019(13)
O1W 0.0835(12) 0.0612(10) 0.0456(8) -0.0031(8) 0.0234(8) -0.0182(9)
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
S1 C1U 1.6649(18) . ?
S2 C2U 1.6620(18) . ?
N1U C1U 1.370(2) . ?
N1U C2U 1.381(2) . ?
N1U H1U 0.802(15) . ?
N2U C4U 1.354(3) . ?
N2U C1U 1.355(2) . ?
N2U H2U 0.838(15) . ?
C2U C3U 1.421(3) . ?
C3U C4U 1.337(3) . ?
C3U H3U 0.9300 . ?
C4U H4U 0.9300 . ?
O1 C18 1.411(3) . ?
O1 C2 1.415(3) . ?
C2 C3 1.456(5) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 O4 1.428(3) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
O4 C5 1.411(3) . ?
C5 C6 1.476(4) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 O7 1.421(3) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
O7 C8 1.409(3) . ?
C8 C9 1.484(4) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 O10 1.429(3) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
O10 C11 1.427(4) . ?
C11 C12 1.496(5) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 O13 1.404(3) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
O13 C14 1.433(3) . ?
C14 C15 1.461(4) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 O16 1.403(3) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
O16 C17 1.439(3) . ?
C17 C18 1.454(3) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
O1W H1W 0.841(16) . ?
O1W H2W 0.837(16) . ?