Buy article online - an online subscription or single-article purchase is required to access this article.
Download citation
Download citation
link to html
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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804027308/bt6556sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804027308/bt6556Isup2.hkl
Contains datablock I

CCDC reference: 259101

Key indicators

  • Single-crystal X-ray study
  • T = 295 K
  • Mean [sigma](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

Computing details top

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·C5H5NOF(000) = 528
Mr = 253.22Dx = 1.448 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 5340 reflections
a = 17.993 (4) Åθ = 3.3–27.5°
b = 6.528 (1) ŵ = 0.12 mm1
c = 12.501 (3) ÅT = 295 K
β = 127.74 (3)°Prism, colorless
V = 1161.2 (4) Å30.38 × 0.24 × 0.18 mm
Z = 4
Data collection top
Rigaku R-AXIS RAPID
diffractometer
1338 independent reflections
Radiation source: fine-focus sealed tube1010 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.016
ω scansθmax = 27.5°, θmin = 3.3°
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)
h = 2323
Tmin = 0.858, Tmax = 0.979k = 78
5541 measured reflectionsl = 1616
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.037All 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 reflectionsΔρmax = 0.21 e Å3
108 parametersΔρmin = 0.17 e Å3
6 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.005 (2)
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
O10.2786 (1)0.4265 (2)0.5209 (1)0.0661 (4)
O20.50000.7139 (2)0.25000.0605 (4)
O30.4637 (1)0.9979 (2)0.2932 (2)0.0872 (5)
N10.4023 (1)0.5926 (2)0.3515 (1)0.0531 (3)
N20.50000.9060 (3)0.25000.0524 (4)
C10.3961 (1)0.7254 (2)0.4275 (2)0.0570 (4)
C20.3550 (1)0.6731 (2)0.4850 (2)0.0584 (4)
C30.3181 (1)0.4757 (2)0.4663 (1)0.0491 (4)
C40.3268 (1)0.3394 (2)0.3869 (1)0.0526 (4)
C50.3683 (1)0.4023 (2)0.3314 (2)0.0553 (4)
H1o0.255 (3)0.306 (3)0.502 (4)0.053 (9)*0.50
H1n0.427 (1)0.632 (3)0.312 (2)0.076 (5)*
H10.423 (1)0.856 (2)0.437 (2)0.071 (5)*
H20.351 (1)0.767 (2)0.539 (2)0.075 (5)*
H40.306 (1)0.202 (2)0.375 (2)0.065 (5)*
H50.376 (1)0.315 (2)0.277 (1)0.065 (5)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.083 (1)0.072 (1)0.081 (1)0.010 (1)0.069 (1)0.006 (1)
O20.081 (1)0.047 (1)0.088 (1)0.0000.069 (1)0.000
O30.138 (1)0.061 (1)0.129 (1)0.003 (1)0.115 (1)0.009 (1)
N10.058 (1)0.063 (1)0.057 (1)0.001 (1)0.045 (1)0.004 (1)
N20.068 (1)0.050 (1)0.058 (1)0.0000.048 (1)0.000
C10.066 (1)0.054 (1)0.064 (1)0.007 (1)0.047 (1)0.001 (1)
C20.073 (1)0.057 (1)0.065 (1)0.006 (1)0.053 (1)0.009 (1)
C30.051 (1)0.059 (1)0.050 (1)0.000 (1)0.037 (1)0.002 (1)
C40.060 (1)0.053 (1)0.058 (1)0.005 (1)0.043 (1)0.004 (1)
C50.064 (1)0.062 (1)0.058 (1)0.003 (1)0.046 (1)0.003 (1)
Geometric parameters (Å, º) top
O1—C31.291 (2)C3—C41.411 (2)
O2—N21.254 (2)C4—C51.358 (2)
O3—N21.228 (1)O1—H1o0.86 (1)
N1—C11.339 (2)N1—H1n0.87 (1)
N1—C51.339 (2)C1—H10.95 (1)
N2—O3i1.228 (1)C2—H20.95 (1)
C1—C21.354 (2)C4—H40.95 (1)
C2—C31.403 (2)C5—H50.96 (1)
C1—N1—C5120.6 (1)C3—O1—H1o115 (3)
O2—N2—O3119.3 (1)C1—N1—H1n120 (1)
O2—N2—O3i119.3 (1)C5—N1—H1n120 (1)
O3—N2—O3i121.5 (2)N1—C1—H1115 (1)
N1—C1—C2121.5 (2)C2—C1—H1124 (1)
C1—C2—C3120.0 (1)C1—C2—H2122 (1)
O1—C3—C2119.9 (1)C3—C2—H2118 (1)
O1—C3—C4123.3 (1)C5—C4—H4120 (1)
C2—C3—C4116.8 (1)C3—C4—H4120 (1)
C3—C4—C5120.1 (1)N1—C5—H5116 (1)
N1—C5—C4121.0 (1)C4—C5—H5123 (1)
C5—N1—C1—C20.7 (2)O1—C3—C4—C5179.3 (2)
N1—C1—C2—C30.4 (3)C2—C3—C4—C50.8 (2)
C1—C2—C3—O1179.8 (2)C1—N1—C5—C40.2 (2)
C1—C2—C3—C40.3 (2)C3—C4—C5—N10.6 (2)
Symmetry code: (i) x+1, y, z+1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1n···O20.87 (1)1.97 (1)2.840 (1)172 (2)
O1—H1o···O1ii0.86 (1)1.59 (1)2.446 (3)174 (4)
Symmetry code: (ii) x+1/2, y+1/2, z+1.
 

Subscribe to Acta Crystallographica Section E: Crystallographic Communications

The full text of this article is available to subscribers to the journal.

If you have already registered and are using a computer listed in your registration details, please email support@iucr.org for assistance.

Buy online

You may purchase this article in PDF and/or HTML formats. For purchasers in the European Community who do not have a VAT number, VAT will be added at the local rate. Payments to the IUCr are handled by WorldPay, who will accept payment by credit card in several currencies. To purchase the article, please complete the form below (fields marked * are required), and then click on `Continue'.
E-mail address* 
Repeat e-mail address* 
(for error checking) 

Format*   PDF (US $40)
   HTML (US $40)
   PDF+HTML (US $50)
In order for VAT to be shown for your country javascript needs to be enabled.

VAT number 
(non-UK EC countries only) 
Country* 
 

Terms and conditions of use
Contact us

Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds