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The crystal structure of the title salt adduct, C5H6NO+·NO3-·C5H5NO, has a C5H6NO+/C5HNO cation/molecule assembly (which lies on an inversion center) whose components are linked through their O atoms by a short hydrogen bond [2.446 (3) Å]. The cation is formally the 4-hydroxypyridinium cation and the neutral component the 4-pyridinone molecule, but the two could not be differentiated as they occupy equivalent positions, with the H atom disordered between them. The nitrogen-bound H atom interacts with the nitrate ion [2.840 (1) Å], which lies on another special position of site symmetry 2.
Supporting information
CCDC reference: 259101
Key indicators
- Single-crystal X-ray study
- T = 295 K
- Mean (C-C) = 0.003 Å
- R factor = 0.037
- wR factor = 0.117
- Data-to-parameter ratio = 12.4
checkCIF/PLATON results
No syntax errors found
Alert level C
ABSTM02_ALERT_3_C The ratio of expected to reported Tmax/Tmin(RR') is < 0.90
Tmin and Tmax reported: 0.858 0.979
Tmin' and Tmax expected: 0.955 0.979
RR' = 0.898
Please check that your absorption correction is appropriate.
CELLV02_ALERT_1_C The supplied cell volume s.u. differs from that
calculated from the cell parameter s.u.'s by > 2
Calculated cell volume su = 6.30
Cell volume su given = 4.00
PLAT031_ALERT_4_C Refined Extinction Parameter within Range ...... 2.50 Sigma
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ?
PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large ............. 0.90
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ?
PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors for N2
PLAT764_ALERT_4_C Overcomplete CIF Bond List Detected (Rep/Expd) . 1.11 Ratio
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
8 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
3 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
2 ALERT type 3 Indicator that the structure quality may be low
2 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.
4-Hydroxypyridinium nitrate 4-hydroxypyridine
top
Crystal data top
C5H6NO+·NO3−·C5H5NO | F(000) = 528 |
Mr = 253.22 | Dx = 1.448 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -C 2yc | Cell parameters from 5340 reflections |
a = 17.993 (4) Å | θ = 3.3–27.5° |
b = 6.528 (1) Å | µ = 0.12 mm−1 |
c = 12.501 (3) Å | T = 295 K |
β = 127.74 (3)° | Prism, colorless |
V = 1161.2 (4) Å3 | 0.38 × 0.24 × 0.18 mm |
Z = 4 | |
Data collection top
Rigaku R-AXIS RAPID diffractometer | 1338 independent reflections |
Radiation source: fine-focus sealed tube | 1010 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.016 |
ω scans | θmax = 27.5°, θmin = 3.3° |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | h = −23→23 |
Tmin = 0.858, Tmax = 0.979 | k = −7→8 |
5541 measured reflections | l = −16→16 |
Refinement top
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)] = 0.037 | All H-atom parameters refined |
wR(F2) = 0.117 | w = 1/[σ2(Fo2) + (0.0639P)2 + 0.2278P] where P = (Fo2 + 2Fc2)/3 |
S = 1.08 | (Δ/σ)max = 0.001 |
1338 reflections | Δρmax = 0.21 e Å−3 |
108 parameters | Δρmin = −0.17 e Å−3 |
6 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.005 (2) |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
O1 | 0.2786 (1) | 0.4265 (2) | 0.5209 (1) | 0.0661 (4) | |
O2 | 0.5000 | 0.7139 (2) | 0.2500 | 0.0605 (4) | |
O3 | 0.4637 (1) | 0.9979 (2) | 0.2932 (2) | 0.0872 (5) | |
N1 | 0.4023 (1) | 0.5926 (2) | 0.3515 (1) | 0.0531 (3) | |
N2 | 0.5000 | 0.9060 (3) | 0.2500 | 0.0524 (4) | |
C1 | 0.3961 (1) | 0.7254 (2) | 0.4275 (2) | 0.0570 (4) | |
C2 | 0.3550 (1) | 0.6731 (2) | 0.4850 (2) | 0.0584 (4) | |
C3 | 0.3181 (1) | 0.4757 (2) | 0.4663 (1) | 0.0491 (4) | |
C4 | 0.3268 (1) | 0.3394 (2) | 0.3869 (1) | 0.0526 (4) | |
C5 | 0.3683 (1) | 0.4023 (2) | 0.3314 (2) | 0.0553 (4) | |
H1o | 0.255 (3) | 0.306 (3) | 0.502 (4) | 0.053 (9)* | 0.50 |
H1n | 0.427 (1) | 0.632 (3) | 0.312 (2) | 0.076 (5)* | |
H1 | 0.423 (1) | 0.856 (2) | 0.437 (2) | 0.071 (5)* | |
H2 | 0.351 (1) | 0.767 (2) | 0.539 (2) | 0.075 (5)* | |
H4 | 0.306 (1) | 0.202 (2) | 0.375 (2) | 0.065 (5)* | |
H5 | 0.376 (1) | 0.315 (2) | 0.277 (1) | 0.065 (5)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.083 (1) | 0.072 (1) | 0.081 (1) | −0.010 (1) | 0.069 (1) | −0.006 (1) |
O2 | 0.081 (1) | 0.047 (1) | 0.088 (1) | 0.000 | 0.069 (1) | 0.000 |
O3 | 0.138 (1) | 0.061 (1) | 0.129 (1) | 0.003 (1) | 0.115 (1) | −0.009 (1) |
N1 | 0.058 (1) | 0.063 (1) | 0.057 (1) | −0.001 (1) | 0.045 (1) | 0.004 (1) |
N2 | 0.068 (1) | 0.050 (1) | 0.058 (1) | 0.000 | 0.048 (1) | 0.000 |
C1 | 0.066 (1) | 0.054 (1) | 0.064 (1) | −0.007 (1) | 0.047 (1) | −0.001 (1) |
C2 | 0.073 (1) | 0.057 (1) | 0.065 (1) | −0.006 (1) | 0.053 (1) | −0.009 (1) |
C3 | 0.051 (1) | 0.059 (1) | 0.050 (1) | 0.000 (1) | 0.037 (1) | 0.002 (1) |
C4 | 0.060 (1) | 0.053 (1) | 0.058 (1) | −0.005 (1) | 0.043 (1) | −0.004 (1) |
C5 | 0.064 (1) | 0.062 (1) | 0.058 (1) | 0.003 (1) | 0.046 (1) | −0.003 (1) |
Geometric parameters (Å, º) top
O1—C3 | 1.291 (2) | C3—C4 | 1.411 (2) |
O2—N2 | 1.254 (2) | C4—C5 | 1.358 (2) |
O3—N2 | 1.228 (1) | O1—H1o | 0.86 (1) |
N1—C1 | 1.339 (2) | N1—H1n | 0.87 (1) |
N1—C5 | 1.339 (2) | C1—H1 | 0.95 (1) |
N2—O3i | 1.228 (1) | C2—H2 | 0.95 (1) |
C1—C2 | 1.354 (2) | C4—H4 | 0.95 (1) |
C2—C3 | 1.403 (2) | C5—H5 | 0.96 (1) |
| | | |
C1—N1—C5 | 120.6 (1) | C3—O1—H1o | 115 (3) |
O2—N2—O3 | 119.3 (1) | C1—N1—H1n | 120 (1) |
O2—N2—O3i | 119.3 (1) | C5—N1—H1n | 120 (1) |
O3—N2—O3i | 121.5 (2) | N1—C1—H1 | 115 (1) |
N1—C1—C2 | 121.5 (2) | C2—C1—H1 | 124 (1) |
C1—C2—C3 | 120.0 (1) | C1—C2—H2 | 122 (1) |
O1—C3—C2 | 119.9 (1) | C3—C2—H2 | 118 (1) |
O1—C3—C4 | 123.3 (1) | C5—C4—H4 | 120 (1) |
C2—C3—C4 | 116.8 (1) | C3—C4—H4 | 120 (1) |
C3—C4—C5 | 120.1 (1) | N1—C5—H5 | 116 (1) |
N1—C5—C4 | 121.0 (1) | C4—C5—H5 | 123 (1) |
| | | |
C5—N1—C1—C2 | −0.7 (2) | O1—C3—C4—C5 | 179.3 (2) |
N1—C1—C2—C3 | 0.4 (3) | C2—C3—C4—C5 | −0.8 (2) |
C1—C2—C3—O1 | −179.8 (2) | C1—N1—C5—C4 | 0.2 (2) |
C1—C2—C3—C4 | 0.3 (2) | C3—C4—C5—N1 | 0.6 (2) |
Symmetry code: (i) −x+1, y, −z+1/2. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1n···O2 | 0.87 (1) | 1.97 (1) | 2.840 (1) | 172 (2) |
O1—H1o···O1ii | 0.86 (1) | 1.59 (1) | 2.446 (3) | 174 (4) |
Symmetry code: (ii) −x+1/2, −y+1/2, −z+1. |
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