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In the title compound, C8H12NO3+·NO3-, the protonated pyridoxinium cations and the nitrate anions are arranged nearly parallel to each other. The aggregation of cations and anions through hydrogen bonds forms a sheet-like structure in parallel planes. An intra­molecular hydrogen bond links the phenol OH and the -CH2OH group, characteristic feature of pyridoxine structures.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806031965/sj2104sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806031965/sj2104Isup2.hkl
Contains datablock I

CCDC reference: 621495

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.041
  • wR factor = 0.129
  • Data-to-parameter ratio = 12.1

checkCIF/PLATON results

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Alert level C PLAT031_ALERT_4_C Refined Extinction Parameter within Range ...... 3.00 Sigma PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.98 PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ? PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for N11
Alert level G PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 2 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 0 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXTL/PC (Bruker, 2000); program(s) used to refine structure: SHELXTL/PC; molecular graphics: Mercury (Macrae et al., 2006) and PLATON (Spek, 2003); software used to prepare material for publication: SHELXTL/PC.

Pyridoxinium nitrate top
Crystal data top
C8H12NO3+·NO3F(000) = 976
Mr = 232.20Dx = 1.497 Mg m3
Dm = 1.49 Mg m3
Dm measured by flotation in a mixture of xylene and bromoform
Monoclinic, C2/cMo Kα radiation, λ = 0.71069 Å
Hall symbol: -C 2ycCell parameters from 25 reflections
a = 18.6810 (11) Åθ = 11.0–14.0°
b = 9.0430 (7) ŵ = 0.13 mm1
c = 13.6950 (9) ÅT = 293 K
β = 117.046 (9)°Block, colourless
V = 2060.5 (2) Å30.24 × 0.21 × 0.19 mm
Z = 8
Data collection top
Nonius MACH3 sealed-tube
diffractometer
1385 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.014
Graphite monochromatorθmax = 25.0°, θmin = 2.5°
ω–2θ scansh = 022
Absorption correction: ψ scan
(North et al., 1968)
k = 110
Tmin = 0.958, Tmax = 0.996l = 1614
2125 measured reflections3 standard reflections every 60 min
1813 independent reflections intensity decay: none
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)] = 0.041H-atom parameters constrained
wR(F2) = 0.129 w = 1/[σ2(Fo2) + (0.061P)2 + 1.481P]
where P = (Fo2 + 2Fc2)/3
S = 1.09(Δ/σ)max < 0.001
1813 reflectionsΔρmax = 0.24 e Å3
150 parametersΔρmin = 0.15 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0009 (3)
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N10.93133 (10)0.46469 (18)1.05695 (13)0.0481 (4)
H10.96050.54041.08870.058*
C20.85740 (12)0.4889 (2)0.97512 (16)0.0463 (5)
C210.82986 (14)0.6442 (2)0.9452 (2)0.0644 (7)
H21A0.85530.70601.00890.097*
H21B0.77260.64890.91780.097*
H21C0.84390.67800.88970.097*
C30.81074 (12)0.3650 (2)0.92467 (16)0.0479 (5)
O30.73697 (10)0.39533 (19)0.84236 (14)0.0722 (5)
H30.71040.31910.82360.108*
C40.84028 (12)0.2226 (2)0.95901 (16)0.0462 (5)
C410.79243 (14)0.0850 (3)0.9065 (2)0.0596 (6)
H41A0.81240.04050.85920.072*
H41B0.79870.01390.96280.072*
O420.71028 (11)0.1207 (2)0.84434 (18)0.0826 (6)
H420.68450.04490.81850.124*
C50.91854 (13)0.2065 (2)1.04507 (16)0.0467 (5)
C510.95451 (15)0.0560 (3)1.0861 (2)0.0607 (6)
H51A0.92840.01021.12560.073*
H51B0.94650.00711.02460.073*
O521.03790 (11)0.07242 (19)1.15651 (15)0.0750 (6)
H521.05690.00761.18440.113*
C60.96256 (12)0.3303 (2)1.09238 (16)0.0494 (5)
H61.01440.32141.14930.059*
N110.91909 (10)0.3014 (2)0.78179 (14)0.0503 (5)
O110.86920 (11)0.2084 (2)0.72804 (17)0.0873 (6)
O120.98481 (10)0.26253 (18)0.85821 (13)0.0650 (5)
O130.90772 (10)0.43554 (19)0.76429 (16)0.0789 (6)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0449 (9)0.0420 (9)0.0475 (9)0.0050 (8)0.0124 (8)0.0063 (8)
C20.0432 (11)0.0438 (11)0.0444 (11)0.0018 (8)0.0134 (9)0.0008 (9)
C210.0569 (13)0.0469 (13)0.0677 (15)0.0009 (11)0.0094 (11)0.0008 (11)
C30.0423 (10)0.0482 (12)0.0447 (11)0.0042 (9)0.0123 (9)0.0026 (9)
O30.0504 (9)0.0580 (10)0.0730 (11)0.0066 (7)0.0025 (8)0.0005 (9)
C40.0504 (12)0.0442 (12)0.0452 (11)0.0071 (9)0.0226 (10)0.0056 (9)
C410.0597 (14)0.0498 (13)0.0660 (14)0.0122 (10)0.0257 (12)0.0104 (10)
O420.0602 (10)0.0639 (12)0.1054 (15)0.0218 (9)0.0217 (10)0.0222 (11)
C50.0540 (12)0.0445 (11)0.0441 (11)0.0013 (9)0.0243 (10)0.0003 (9)
C510.0715 (15)0.0467 (13)0.0616 (14)0.0049 (11)0.0281 (12)0.0031 (11)
O520.0711 (11)0.0607 (11)0.0737 (11)0.0192 (9)0.0158 (9)0.0094 (9)
C60.0458 (11)0.0493 (12)0.0446 (11)0.0018 (9)0.0132 (9)0.0011 (9)
N110.0411 (9)0.0493 (11)0.0544 (10)0.0045 (8)0.0164 (8)0.0007 (9)
O110.0630 (11)0.0874 (14)0.0921 (13)0.0323 (10)0.0183 (10)0.0246 (11)
O120.0554 (9)0.0523 (9)0.0642 (10)0.0073 (7)0.0071 (8)0.0099 (7)
O130.0515 (10)0.0526 (11)0.1037 (14)0.0093 (8)0.0101 (9)0.0181 (9)
Geometric parameters (Å, º) top
N1—C61.340 (3)C41—H41A0.9700
N1—C21.343 (2)C41—H41B0.9700
N1—H10.8600O42—H420.8200
C2—C31.394 (3)C5—C61.366 (3)
C2—C211.488 (3)C5—C511.509 (3)
C21—H21A0.9600C51—O521.419 (3)
C21—H21B0.9600C51—H51A0.9700
C21—H21C0.9600C51—H51B0.9700
C3—O31.354 (2)O52—H520.8200
C3—C41.396 (3)C6—H60.9300
O3—H30.8200N11—O111.222 (2)
C4—C51.407 (3)N11—O131.236 (2)
C4—C411.510 (3)N11—O121.248 (2)
C41—O421.413 (3)
C6—N1—C2124.28 (17)C4—C41—H41A109.6
C6—N1—H1117.9O42—C41—H41B109.6
C2—N1—H1117.9C4—C41—H41B109.6
N1—C2—C3117.17 (18)H41A—C41—H41B108.1
N1—C2—C21118.63 (18)C41—O42—H42109.5
C3—C2—C21124.19 (18)C6—C5—C4118.99 (19)
C2—C21—H21A109.5C6—C5—C51119.54 (19)
C2—C21—H21B109.5C4—C5—C51121.47 (19)
H21A—C21—H21B109.5O52—C51—C5108.90 (18)
C2—C21—H21C109.5O52—C51—H51A109.9
H21A—C21—H21C109.5C5—C51—H51A109.9
H21B—C21—H21C109.5O52—C51—H51B109.9
O3—C3—C2114.86 (19)C5—C51—H51B109.9
O3—C3—C4124.35 (18)H51A—C51—H51B108.3
C2—C3—C4120.79 (18)C51—O52—H52109.5
C3—O3—H3109.5N1—C6—C5120.18 (18)
C3—C4—C5118.58 (18)N1—C6—H6119.9
C3—C4—C41122.81 (19)C5—C6—H6119.9
C5—C4—C41118.60 (19)O11—N11—O13122.80 (19)
O42—C41—C4110.16 (19)O11—N11—O12120.08 (19)
O42—C41—H41A109.6O13—N11—O12117.12 (17)
C6—N1—C2—C30.1 (3)C5—C4—C41—O42164.26 (19)
C6—N1—C2—C21179.1 (2)C3—C4—C5—C60.4 (3)
N1—C2—C3—O3179.63 (18)C41—C4—C5—C6179.37 (19)
C21—C2—C3—O31.4 (3)C3—C4—C5—C51179.72 (19)
N1—C2—C3—C40.3 (3)C41—C4—C5—C510.8 (3)
C21—C2—C3—C4178.6 (2)C6—C5—C51—O5211.6 (3)
O3—C3—C4—C5179.4 (2)C4—C5—C51—O52168.53 (19)
C2—C3—C4—C50.6 (3)C2—N1—C6—C50.3 (3)
O3—C3—C4—C410.5 (3)C4—C5—C6—N10.0 (3)
C2—C3—C4—C41179.5 (2)C51—C5—C6—N1179.9 (2)
C3—C4—C41—O4216.8 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—H3···O420.821.822.535 (2)146
N1—H1···O12i0.862.022.869 (2)170
O42—H42···O13ii0.821.862.626 (2)155
O52—H52···O11iii0.822.273.077 (3)170
Symmetry codes: (i) x+2, y+1, z+2; (ii) x+3/2, y1/2, z+3/2; (iii) x+2, y, z+2.
 

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