Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807030164/sg2177sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807030164/sg2177Isup2.hkl |
CCDC reference: 655031
Key indicators
- Single-crystal X-ray study
- T = 292 K
- Mean (C-C) = 0.002 Å
- R factor = 0.036
- wR factor = 0.109
- Data-to-parameter ratio = 12.1
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.57
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
The triclinic polymorph of hypoxanthine was described by Schmalle et al. (1988). There are different weak intermolecular contacts of the form C2—H2···N2iii and C5—H5···O1ii (Taylor & Kennard, 1982).
Hydrothermal treatment of Ba(ClO4)2.6H2O(0.1332 g, 0.3 mmol), Inosine(0.1610 g, 0.6 mmol), And 95% ethanol solution(4 ml) over three days at 70 oC yielded colorless plate crystals of hypoxanthine(I). The product was isolated, washed three times with 70% ethanol solution, and dried in a vacuum desiccator using CaCl2. Yield: 15%. CH&N analysis: Calculated for C5H4N4O: C 44.12, H 2.96, N 41.16%; found: C 44.05, H 2.93, N 41.04%.
H atoms bonded to C or N atoms were placed in calculated positions, with C—H = 0.95 Å and N—H= 0.88 Å, and were included in the refinement in the riding-model approximation, and Uiso(H) = 1.2Ueq(C or N).
A triclinic polymorph of hypoxanthine (I) has been reported (Schmalle et al., 1988). Here we describe a monoclinic polymorph (Figure1). There are two hydrogen bonds of the type N1—H1···O1i with N1—O1i donor-acceptor distance of 2.7846 (18) Å and N4—H4···N3ii with N4—N3ii donor-acceptor distance of 2.8208 (19) Å (Figure 2). In addition, there are different weak intermolecular contacts (Taylor & Kennard,1982) of the form C2—H2···N2iii with C2—N2iii distance of 3.376 (2) Å and C5—H5···O1ii with C5—O1ii distance of 3.1933 (19) Å (Table 1). Thus, the hypoxanthine molecules form sheets approximately parallel to the (102) plane. The separations between parallel hypoxanthine molecules stacked along the a axis is 3.672 Å (Figure 3).
The triclinic polymorph of hypoxanthine was described by Schmalle et al. (1988). There are different weak intermolecular contacts of the form C2—H2···N2iii and C5—H5···O1ii (Taylor & Kennard, 1982).
Data collection: SMART (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2004); software used to prepare material for publication: SHELXTL.
C5H4N4O | Z = 4 |
Mr = 136.12 | F(000) = 280 |
Monoclinic, P21/c | Dx = 1.595 Mg m−3 |
a = 3.6725 (19) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 17.960 (9) Å | µ = 0.12 mm−1 |
c = 9.010 (5) Å | T = 292 K |
β = 107.469 (19)° | Plate, colorless |
V = 566.9 (5) Å3 | 0.48 × 0.13 × 0.11 mm |
Bruker SMART APEXII CCD area-detector diffractometer | 1113 independent reflections |
Radiation source: fine-focus sealed tube | 964 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.016 |
φ and ω scans | θmax = 26.0°, θmin = 2.3° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −4→4 |
Tmin = 0.979, Tmax = 0.988 | k = −22→21 |
2981 measured reflections | l = −6→11 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.036 | H-atom parameters constrained |
wR(F2) = 0.109 | w = 1/[σ2(Fo2) + (0.0758P)2 + 0.069P] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max < 0.001 |
1113 reflections | Δρmax = 0.19 e Å−3 |
92 parameters | Δρmin = −0.19 e Å−3 |
0 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.067 (11) |
C5H4N4O | V = 566.9 (5) Å3 |
Mr = 136.12 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 3.6725 (19) Å | µ = 0.12 mm−1 |
b = 17.960 (9) Å | T = 292 K |
c = 9.010 (5) Å | 0.48 × 0.13 × 0.11 mm |
β = 107.469 (19)° |
Bruker SMART APEXII CCD area-detector diffractometer | 1113 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 964 reflections with I > 2σ(I) |
Tmin = 0.979, Tmax = 0.988 | Rint = 0.016 |
2981 measured reflections |
R[F2 > 2σ(F2)] = 0.036 | 0 restraints |
wR(F2) = 0.109 | H-atom parameters constrained |
S = 1.04 | Δρmax = 0.19 e Å−3 |
1113 reflections | Δρmin = −0.19 e Å−3 |
92 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 | ||
O1 | 0.5544 (3) | 0.40375 (5) | 0.51583 (12) | 0.0469 (3) | |
N1 | 0.1515 (3) | 0.46886 (6) | 0.31417 (13) | 0.0374 (3) | |
H1 | 0.2213 | 0.5107 | 0.3658 | 0.045* | |
N2 | −0.2451 (3) | 0.41739 (6) | 0.08071 (13) | 0.0388 (3) | |
N3 | 0.2692 (3) | 0.26683 (6) | 0.31153 (13) | 0.0367 (3) | |
N4 | −0.1664 (3) | 0.28307 (6) | 0.08049 (13) | 0.0377 (3) | |
H4 | −0.3275 | 0.2721 | −0.0109 | 0.045* | |
C1 | 0.3174 (4) | 0.40330 (7) | 0.38534 (16) | 0.0339 (3) | |
C2 | −0.1094 (4) | 0.47339 (8) | 0.17154 (16) | 0.0395 (4) | |
H2 | −0.2006 | 0.5216 | 0.1350 | 0.047* | |
C3 | −0.0906 (4) | 0.35170 (7) | 0.14506 (15) | 0.0329 (3) | |
C4 | 0.1784 (3) | 0.34128 (7) | 0.28815 (14) | 0.0317 (3) | |
C5 | 0.0550 (4) | 0.23473 (8) | 0.18446 (16) | 0.0394 (4) | |
H5 | 0.0552 | 0.1826 | 0.1670 | 0.047* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0569 (7) | 0.0343 (6) | 0.0312 (6) | −0.0004 (4) | −0.0145 (5) | −0.0024 (4) |
N1 | 0.0449 (7) | 0.0273 (6) | 0.0308 (7) | 0.0004 (4) | −0.0026 (5) | 0.0000 (4) |
N2 | 0.0406 (6) | 0.0380 (7) | 0.0284 (6) | 0.0014 (5) | −0.0038 (5) | 0.0046 (5) |
N3 | 0.0422 (6) | 0.0294 (6) | 0.0289 (6) | 0.0001 (4) | −0.0039 (5) | 0.0000 (4) |
N4 | 0.0407 (6) | 0.0380 (7) | 0.0233 (6) | −0.0042 (4) | −0.0075 (5) | −0.0041 (4) |
C1 | 0.0358 (6) | 0.0322 (7) | 0.0261 (7) | −0.0012 (5) | −0.0023 (5) | 0.0016 (5) |
C2 | 0.0429 (7) | 0.0355 (7) | 0.0318 (8) | 0.0036 (5) | −0.0013 (6) | 0.0062 (5) |
C3 | 0.0340 (6) | 0.0348 (7) | 0.0244 (7) | −0.0014 (5) | 0.0004 (5) | 0.0012 (5) |
C4 | 0.0338 (7) | 0.0299 (7) | 0.0247 (7) | −0.0005 (5) | −0.0014 (5) | 0.0018 (5) |
C5 | 0.0446 (8) | 0.0320 (7) | 0.0317 (8) | −0.0016 (5) | −0.0035 (6) | −0.0029 (5) |
O1—C1 | 1.2352 (17) | N4—C5 | 1.3546 (17) |
N1—C2 | 1.3553 (18) | N4—C3 | 1.3557 (17) |
N1—C1 | 1.3908 (17) | N4—H4 | 0.8800 |
N1—H1 | 0.8800 | C1—C4 | 1.4141 (18) |
N2—C2 | 1.2980 (18) | C2—H2 | 0.9500 |
N2—C3 | 1.3612 (17) | C3—C4 | 1.3815 (19) |
N3—C5 | 1.3118 (17) | C5—H5 | 0.9500 |
N3—C4 | 1.3788 (18) | ||
C2—N1—C1 | 125.10 (11) | N2—C2—H2 | 117.3 |
C2—N1—H1 | 117.4 | N1—C2—H2 | 117.3 |
C1—N1—H1 | 117.4 | N4—C3—N2 | 126.84 (12) |
C2—N2—C3 | 111.78 (12) | N4—C3—C4 | 105.93 (11) |
C5—N3—C4 | 103.81 (11) | N2—C3—C4 | 127.22 (12) |
C5—N4—C3 | 106.41 (11) | N3—C4—C3 | 110.26 (11) |
C5—N4—H4 | 126.8 | N3—C4—C1 | 130.06 (12) |
C3—N4—H4 | 126.8 | C3—C4—C1 | 119.69 (12) |
O1—C1—N1 | 121.29 (11) | N3—C5—N4 | 113.58 (13) |
O1—C1—C4 | 127.93 (11) | N3—C5—H5 | 123.2 |
N1—C1—C4 | 110.78 (12) | N4—C5—H5 | 123.2 |
N2—C2—N1 | 125.43 (13) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O1i | 0.88 | 1.91 | 2.7846 (18) | 172 |
N4—H4···N3ii | 0.88 | 1.95 | 2.8208 (19) | 168 |
C2—H2···N2iii | 0.95 | 2.60 | 3.376 (2) | 139 |
C5—H5···O1ii | 0.95 | 2.48 | 3.1933 (19) | 132 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x−1, −y+1/2, z−1/2; (iii) −x−1, −y+1, −z. |
Experimental details
Crystal data | |
Chemical formula | C5H4N4O |
Mr | 136.12 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 292 |
a, b, c (Å) | 3.6725 (19), 17.960 (9), 9.010 (5) |
β (°) | 107.469 (19) |
V (Å3) | 566.9 (5) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.12 |
Crystal size (mm) | 0.48 × 0.13 × 0.11 |
Data collection | |
Diffractometer | Bruker SMART APEXII CCD area-detector |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.979, 0.988 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 2981, 1113, 964 |
Rint | 0.016 |
(sin θ/λ)max (Å−1) | 0.617 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.036, 0.109, 1.04 |
No. of reflections | 1113 |
No. of parameters | 92 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.19, −0.19 |
Computer programs: SMART (Bruker, 2004), SAINT (Bruker, 2004), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 2004), SHELXTL.
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O1i | 0.88 | 1.91 | 2.7846 (18) | 171.8 |
N4—H4···N3ii | 0.88 | 1.95 | 2.8208 (19) | 167.9 |
C2—H2···N2iii | 0.95 | 2.60 | 3.376 (2) | 139.4 |
C5—H5···O1ii | 0.95 | 2.48 | 3.1933 (19) | 132.1 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x−1, −y+1/2, z−1/2; (iii) −x−1, −y+1, −z. |
Subscribe to Acta Crystallographica Section E: Crystallographic Communications
The full text of this article is available to subscribers to the journal.
- Information on subscribing
- Sample issue
- If you have already subscribed, you may need to register
A triclinic polymorph of hypoxanthine (I) has been reported (Schmalle et al., 1988). Here we describe a monoclinic polymorph (Figure1). There are two hydrogen bonds of the type N1—H1···O1i with N1—O1i donor-acceptor distance of 2.7846 (18) Å and N4—H4···N3ii with N4—N3ii donor-acceptor distance of 2.8208 (19) Å (Figure 2). In addition, there are different weak intermolecular contacts (Taylor & Kennard,1982) of the form C2—H2···N2iii with C2—N2iii distance of 3.376 (2) Å and C5—H5···O1ii with C5—O1ii distance of 3.1933 (19) Å (Table 1). Thus, the hypoxanthine molecules form sheets approximately parallel to the (102) plane. The separations between parallel hypoxanthine molecules stacked along the a axis is 3.672 Å (Figure 3).