Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803000953/dn6052sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536803000953/dn6052Isup2.hkl |
CCDC reference: 204697
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.003 Å
- R factor = 0.032
- wR factor = 0.081
- Data-to-parameter ratio = 11.3
checkCIF results
No syntax errors found ADDSYM reports no extra symmetry
Alert Level C:
REFLT_03 From the CIF: _diffrn_reflns_theta_max 26.36 From the CIF: _reflns_number_total 1821 TEST2: Reflns within _diffrn_reflns_theta_max Count of symmetry unique reflns 1981 Completeness (_total/calc) 91.92% Alert C: < 95% complete
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
1 Alert Level C = Please check
Colorless single crystals of guaninium sulfate monohydrate were obtained after two weeks by slow evaporation at room temperature of an equimolar solution of guanine and sulfuric acid.
H atoms attached to C and N atoms were fixed at localized positions and refined using a riding model. H atoms belonging to the water molecule were refined with an overal isotropic displacement parameter using restraints.
Data collection: KappaCCD Reference Manual (Nonius, 1998); cell refinement: DENZO and SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO and SCALEPACK; program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrujia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).
C5H7N5O2+·SO42−·H2O | F(000) = 552 |
Mr = 267.24 | Dx = 1.823 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 6875 reflections |
a = 8.9940 (3) Å | θ = 2.8–26.4° |
b = 10.2020 (2) Å | µ = 0.37 mm−1 |
c = 11.0440 (3) Å | T = 293 K |
β = 106.04 (2)° | Plate, colorless |
V = 973.9 (1) Å3 | 0.4 × 0.1 × 0.01 mm |
Z = 4 |
Nonius KappaCCD diffractometer | 1631 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.033 |
Graphite monochromator | θmax = 26.4°, θmin = 2.8° |
ϕ scans | h = −11→11 |
6875 measured reflections | k = −12→12 |
1821 independent reflections | l = −12→12 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.032 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.081 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.11 | w = 1/[σ2(Fo2) + (0.0361P)2 + 0.4753P] where P = (Fo2 + 2Fc2)/3 |
1821 reflections | (Δ/σ)max < 0.001 |
161 parameters | Δρmax = 0.26 e Å−3 |
1 restraint | Δρmin = −0.41 e Å−3 |
C5H7N5O2+·SO42−·H2O | V = 973.9 (1) Å3 |
Mr = 267.24 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 8.9940 (3) Å | µ = 0.37 mm−1 |
b = 10.2020 (2) Å | T = 293 K |
c = 11.0440 (3) Å | 0.4 × 0.1 × 0.01 mm |
β = 106.04 (2)° |
Nonius KappaCCD diffractometer | 1631 reflections with I > 2σ(I) |
6875 measured reflections | Rint = 0.033 |
1821 independent reflections |
R[F2 > 2σ(F2)] = 0.032 | 1 restraint |
wR(F2) = 0.081 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.11 | Δρmax = 0.26 e Å−3 |
1821 reflections | Δρmin = −0.41 e Å−3 |
161 parameters |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
S1 | 0.15170 (5) | 0.18894 (4) | 0.76616 (4) | 0.01967 (15) | |
O1 | 0.07493 (16) | 0.06048 (12) | 0.72724 (13) | 0.0277 (3) | |
O4 | 0.23663 (17) | 0.22839 (13) | 0.67648 (14) | 0.0312 (3) | |
O3 | 0.03023 (17) | 0.28698 (12) | 0.76575 (14) | 0.0320 (3) | |
O2 | 0.25598 (18) | 0.17756 (13) | 0.89364 (14) | 0.0357 (4) | |
O6 | 0.39762 (17) | 0.64077 (14) | 0.34702 (14) | 0.0346 (4) | |
N3 | 0.15176 (17) | 0.71507 (13) | 0.59978 (14) | 0.0198 (3) | |
H3 | 0.0981 | 0.7299 | 0.6518 | 0.024* | |
N9 | 0.18591 (17) | 0.94558 (14) | 0.55504 (14) | 0.0203 (3) | |
H9 | 0.1365 | 0.9819 | 0.6026 | 0.024* | |
N7 | 0.32181 (17) | 0.92071 (14) | 0.42100 (14) | 0.0221 (3) | |
H7 | 0.3735 | 0.9382 | 0.3681 | 0.027* | |
N1 | 0.26823 (17) | 0.57203 (14) | 0.48693 (14) | 0.0211 (3) | |
H1 | 0.2857 | 0.4919 | 0.4708 | 0.025* | |
N2 | 0.13960 (18) | 0.49136 (14) | 0.62537 (15) | 0.0244 (3) | |
H2A | 0.0872 | 0.5038 | 0.6787 | 0.029* | |
H2B | 0.1615 | 0.4130 | 0.6073 | 0.029* | |
C4 | 0.2061 (2) | 0.81454 (16) | 0.54207 (17) | 0.0185 (4) | |
C8 | 0.2576 (2) | 1.00756 (17) | 0.47956 (17) | 0.0230 (4) | |
H8 | 0.2614 | 1.0980 | 0.4700 | 0.028* | |
C5 | 0.2918 (2) | 0.79703 (16) | 0.45925 (17) | 0.0197 (4) | |
C2 | 0.18605 (19) | 0.59172 (16) | 0.57161 (16) | 0.0189 (4) | |
C6 | 0.3272 (2) | 0.66855 (17) | 0.42342 (17) | 0.0218 (4) | |
O1W | 0.50847 (16) | 0.42759 (15) | 0.23912 (14) | 0.0326 (4) | |
H1W | 0.438 (3) | 0.367 (2) | 0.225 (3) | 0.059 (6)* | |
H2W | 0.472 (3) | 0.493 (2) | 0.271 (3) | 0.059 (6)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0285 (2) | 0.0127 (2) | 0.0228 (3) | 0.00125 (16) | 0.01545 (18) | 0.00129 (15) |
O1 | 0.0373 (7) | 0.0177 (6) | 0.0332 (8) | −0.0060 (5) | 0.0185 (6) | −0.0062 (5) |
O4 | 0.0410 (8) | 0.0238 (7) | 0.0397 (9) | 0.0050 (6) | 0.0294 (7) | 0.0076 (6) |
O3 | 0.0409 (8) | 0.0187 (7) | 0.0478 (9) | 0.0089 (6) | 0.0313 (7) | 0.0072 (6) |
O2 | 0.0531 (9) | 0.0231 (7) | 0.0276 (9) | −0.0035 (6) | 0.0054 (7) | 0.0021 (5) |
O6 | 0.0496 (9) | 0.0269 (7) | 0.0398 (9) | 0.0010 (6) | 0.0335 (7) | −0.0051 (6) |
N3 | 0.0254 (8) | 0.0176 (7) | 0.0215 (9) | −0.0007 (6) | 0.0147 (6) | −0.0010 (5) |
N9 | 0.0255 (7) | 0.0156 (7) | 0.0225 (8) | 0.0017 (6) | 0.0111 (6) | −0.0023 (6) |
N7 | 0.0289 (8) | 0.0198 (8) | 0.0212 (9) | −0.0028 (6) | 0.0130 (6) | 0.0014 (6) |
N1 | 0.0306 (8) | 0.0145 (7) | 0.0213 (9) | 0.0010 (6) | 0.0123 (6) | −0.0027 (5) |
N2 | 0.0317 (8) | 0.0184 (8) | 0.0266 (9) | −0.0011 (6) | 0.0140 (7) | 0.0024 (6) |
C4 | 0.0215 (8) | 0.0163 (8) | 0.0189 (10) | −0.0009 (6) | 0.0074 (7) | −0.0008 (6) |
C8 | 0.0302 (9) | 0.0167 (8) | 0.0221 (10) | −0.0012 (7) | 0.0075 (7) | 0.0002 (7) |
C5 | 0.0253 (9) | 0.0176 (8) | 0.0196 (10) | −0.0016 (7) | 0.0117 (7) | −0.0004 (6) |
C2 | 0.0205 (8) | 0.0186 (8) | 0.0175 (9) | −0.0006 (6) | 0.0054 (6) | −0.0013 (6) |
C6 | 0.0257 (9) | 0.0205 (9) | 0.0220 (10) | −0.0004 (7) | 0.0113 (7) | −0.0020 (7) |
O1W | 0.0284 (7) | 0.0383 (9) | 0.0367 (9) | −0.0038 (6) | 0.0184 (6) | −0.0123 (6) |
S1—O4 | 1.4643 (13) | N9—C4 | 1.362 (2) |
S1—O2 | 1.4647 (16) | N7—C8 | 1.320 (2) |
S1—O3 | 1.4803 (13) | N7—C5 | 1.381 (2) |
S1—O1 | 1.4883 (13) | N1—C2 | 1.358 (2) |
O6—C6 | 1.220 (2) | N1—C6 | 1.396 (2) |
N3—C2 | 1.352 (2) | N2—C2 | 1.309 (2) |
N3—C4 | 1.359 (2) | C4—C5 | 1.361 (2) |
N9—C8 | 1.345 (2) | C5—C6 | 1.431 (2) |
O4—S1—O2 | 110.90 (9) | C5—C4—N9 | 108.44 (15) |
O4—S1—O3 | 109.55 (8) | N7—C8—N9 | 109.73 (15) |
O2—S1—O3 | 109.42 (9) | C4—C5—N7 | 106.31 (14) |
O4—S1—O1 | 109.50 (8) | C4—C5—C6 | 121.14 (15) |
O2—S1—O1 | 109.31 (8) | N7—C5—C6 | 132.47 (16) |
O3—S1—O1 | 108.12 (8) | N2—C2—N3 | 120.14 (16) |
C2—N3—C4 | 116.90 (15) | N2—C2—N1 | 119.97 (15) |
C8—N9—C4 | 107.20 (14) | N3—C2—N1 | 119.89 (15) |
C8—N7—C5 | 108.32 (15) | O6—C6—N1 | 121.71 (16) |
C2—N1—C6 | 126.63 (14) | O6—C6—C5 | 127.03 (17) |
N3—C4—C5 | 124.13 (15) | N1—C6—C5 | 111.26 (15) |
N3—C4—N9 | 127.43 (15) |
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3···O3i | 0.86 | 1.75 | 2.6011 (19) | 167 |
N9—H9···O1ii | 0.86 | 1.81 | 2.6526 (19) | 167 |
N7—H7···O1Wiii | 0.86 | 1.80 | 2.637 (2) | 164 |
N1—H1···O2iv | 0.86 | 1.91 | 2.738 (2) | 160 |
N2—H2A···O1i | 0.86 | 2.09 | 2.934 (2) | 166 |
N2—H2B···O4 | 0.86 | 2.07 | 2.829 (2) | 146 |
O1W—H1W···O4iv | 0.86 (2) | 2.00 (2) | 2.838 (2) | 164 (3) |
O1W—H2W···O6 | 0.86 (2) | 1.93 (2) | 2.793 (2) | 178 (1) |
Symmetry codes: (i) −x, y+1/2, −z+3/2; (ii) x, y+1, z; (iii) −x+1, y+1/2, −z+1/2; (iv) x, −y+1/2, z−1/2. |
Experimental details
Crystal data | |
Chemical formula | C5H7N5O2+·SO42−·H2O |
Mr | 267.24 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 293 |
a, b, c (Å) | 8.9940 (3), 10.2020 (2), 11.0440 (3) |
β (°) | 106.04 (2) |
V (Å3) | 973.9 (1) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.37 |
Crystal size (mm) | 0.4 × 0.1 × 0.01 |
Data collection | |
Diffractometer | Nonius KappaCCD diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 6875, 1821, 1631 |
Rint | 0.033 |
(sin θ/λ)max (Å−1) | 0.625 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.032, 0.081, 1.11 |
No. of reflections | 1821 |
No. of parameters | 161 |
No. of restraints | 1 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.26, −0.41 |
Computer programs: KappaCCD Reference Manual (Nonius, 1998), DENZO and SCALEPACK (Otwinowski & Minor, 1997), DENZO and SCALEPACK, SIR92 (Altomare et al., 1993), SHELXL97 (Sheldrick, 1997), ORTEP-3 (Farrujia, 1997), WinGX (Farrugia, 1999).
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3···O3i | 0.86 | 1.75 | 2.6011 (19) | 167 |
N9—H9···O1ii | 0.86 | 1.81 | 2.6526 (19) | 167 |
N7—H7···O1Wiii | 0.86 | 1.80 | 2.637 (2) | 164 |
N1—H1···O2iv | 0.86 | 1.91 | 2.738 (2) | 160 |
N2—H2A···O1i | 0.86 | 2.09 | 2.934 (2) | 166 |
N2—H2B···O4 | 0.86 | 2.07 | 2.829 (2) | 146 |
O1W—H1W···O4iv | 0.86 (2) | 2.00 (2) | 2.838 (2) | 164 (3) |
O1W—H2W···O6 | 0.86 (2) | 1.93 (2) | 2.793 (2) | 178 (1) |
Symmetry codes: (i) −x, y+1/2, −z+3/2; (ii) x, y+1, z; (iii) −x+1, y+1/2, −z+1/2; (iv) x, −y+1/2, z−1/2. |
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The structure elucidation of nucleic acids and their derivatives is of interest, because of their widespread biological occurrence (Richards et al., 1972; Perutz & Eyck, 1972). A number of these compounds are effective metabolic inhibitors with useful chemotherapeutic activity (Roy-burman, 1970; Balis, 1968; Hitchings & Elion, 1963). In several crystals of compounds with organic bases and inorganic acids, the structure cohesion is assured by strong hydrogen bonds as was observed in guaninium dinitrate dihydrate (Bouchouit et al., 2002), adeninium sulfate (Langer & Huml, 1978a), adeninium hemisulfate hydrate (Langer & Huml, 1978b) and adeninium hydroboromide hemihydrate (Langer & Huml, 1978c). Two structures of guanine with inorganic acids have been reported, namely guaninium dinitrate dihydrate and guaninium dichloride (Matkovic-Calogovic & Sankovic, 1999).
The determination of the crystal and molecular structure of guaninium sulfate hydrate, (I), forms part of a study on the interactions between organic bases and inorganic acids. The dimensions of the sulfate anion (Fig. 1) are comparable with those found in other sulfates (e.g. Cherouana et al., 2002; Srinivasan et al., 2001). The S—O bond lengths are in the range 1.4653 (16)–1.4874 (13) Å, while the O—S—O angles range from 108.23 (8) to 110.88 (9)°. As was observed in guanium dinitrate dihydrate, the imino groups of the pyrimidine and imidazolyl moieties (N3 and N7) in guanine are protonated. There is an intricate hydrogen-bond network (Fig. 2). The diprotonated guanine in (I) is hydrogen bonded to four sulfate groups [via N1—H1···O2 for the first group, N3—H3···O3 and N2—H21···O1 for the second group, N9—H9···O1 for the third and N2—H21···O3 and N2—H22···O4 for the last group]. We also observed that the water molecule forms three hydrogen bonds with the guaninium and sulfate ions, where it has two different behaviors, viz. as donor with the sulfate anion [via O1w—H1w···O4 and O1w—H2w···O6] and as acceptor with the guaninium ion [via N7—H7···O1w]. This system of hydrogen bonds among the guaninium cations, the sulfate anions and the water molecule generates a succession of layers parallel to the diagonal of ac plane (Fig. 3). Layers of guaninium cations and water molecules are linked by strong anion–cation and anion–water hydrogen bonds via the sandwiched sulfates.