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The crystal structure of the title compound, C9H13N2O2+·I, consists of pyridinium cations and iodide anions stabilized by inter­molecular N—H...I hydrogen bonds, forming one-dimensional chains along [010].

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806019283/lh2083sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806019283/lh2083Isup2.hkl
Contains datablock I

CCDC reference: 610850

Key indicators

  • Single-crystal X-ray study
  • T = 115 K
  • Mean [sigma](C-C)= 0.002 Å
  • R factor = 0.028
  • wR factor = 0.068
  • Data-to-parameter ratio = 41.0

checkCIF/PLATON results

No syntax errors found


No errors found in this datablock

Computing details top

Data collection: COLLECT (Nonius, 2000); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: SCALEPACK and DENZO (Otwinowski & Minor, 1997); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (version 1.07; Farrugia, 1997) and PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97.

4-Amino-(1-ethoxycarbonylmethyl)pyridinium iodide top
Crystal data top
C9H13N2O2+·IF(000) = 1200
Mr = 308.11Dx = 1.738 Mg m3
Orthorhombic, PbcnMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2n 2abCell parameters from 5877 reflections
a = 12.5402 (15) Åθ = 2.5–36.3°
b = 9.8173 (10) ŵ = 2.70 mm1
c = 19.135 (2) ÅT = 115 K
V = 2355.7 (4) Å3Fragment, colorless
Z = 80.25 × 0.22 × 0.20 mm
Data collection top
Bruker–Nonius KappaCCD
diffractometer
5535 independent reflections
Radiation source: fine-focus sealed tube4300 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.021
ω scans with κ offsetsθmax = 36.4°, θmin = 2.6°
Absorption correction: multi-scan
(SCALEPACK; Otwinowski & Minor, 1997)
h = 2020
Tmin = 0.524, Tmax = 0.583k = 1616
36052 measured reflectionsl = 3131
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)] = 0.028H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.068 w = 1/[σ2(Fo2) + (0.0272P)2 + 1.6703P]
where P = (Fo2 + 2Fc2)/3
S = 1.06(Δ/σ)max = 0.001
5535 reflectionsΔρmax = 1.37 e Å3
135 parametersΔρmin = 0.96 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.00249 (13)
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
I10.405389 (9)0.986511 (11)0.362361 (7)0.02060 (4)
O10.39560 (10)0.55695 (13)0.81826 (7)0.0223 (2)
O20.33509 (11)0.45961 (13)0.71919 (7)0.0230 (2)
N10.28417 (12)0.71539 (13)0.66589 (7)0.0182 (2)
N20.22075 (15)0.76726 (17)0.45649 (9)0.0271 (3)
H210.264 (2)0.813 (3)0.4314 (13)0.033*
H220.178 (2)0.718 (2)0.4394 (13)0.033*
C10.35218 (15)0.78728 (17)0.62508 (10)0.0217 (3)
H10.41430.82580.64550.026*
C20.33407 (14)0.80583 (17)0.55571 (9)0.0218 (3)
H20.38280.85760.52850.026*
C30.24258 (13)0.74801 (16)0.52394 (9)0.0193 (3)
C40.17390 (14)0.67153 (17)0.56777 (9)0.0208 (3)
H40.11230.62910.54870.025*
C50.19591 (14)0.65866 (17)0.63709 (9)0.0203 (3)
H50.14830.60870.66600.024*
C60.30583 (15)0.69873 (16)0.74035 (9)0.0221 (3)
H6A0.23950.71480.76720.027*
H6B0.35910.76720.75530.027*
C70.34749 (13)0.55725 (16)0.75628 (9)0.0190 (3)
C80.41984 (15)0.42220 (18)0.84688 (10)0.0233 (3)
H8A0.47000.37320.81580.028*
H8B0.35380.36760.85120.028*
C90.46905 (18)0.4435 (2)0.91722 (11)0.0326 (4)
H9A0.53760.49040.91190.049*
H9B0.48050.35510.93980.049*
H9C0.42130.49910.94610.049*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
I10.01526 (6)0.01929 (6)0.02726 (7)0.00075 (3)0.00035 (4)0.00264 (3)
O10.0286 (7)0.0182 (5)0.0201 (6)0.0009 (5)0.0050 (5)0.0009 (4)
O20.0283 (6)0.0188 (5)0.0218 (6)0.0003 (5)0.0017 (5)0.0027 (4)
N10.0207 (6)0.0153 (5)0.0187 (6)0.0014 (5)0.0013 (5)0.0003 (4)
N20.0320 (8)0.0288 (8)0.0205 (7)0.0078 (6)0.0009 (6)0.0015 (6)
C10.0203 (8)0.0187 (7)0.0262 (8)0.0058 (6)0.0010 (6)0.0000 (6)
C20.0210 (8)0.0203 (7)0.0241 (8)0.0069 (6)0.0016 (6)0.0018 (6)
C30.0203 (7)0.0167 (6)0.0207 (7)0.0010 (5)0.0010 (6)0.0002 (5)
C40.0181 (7)0.0206 (7)0.0237 (8)0.0040 (5)0.0016 (6)0.0008 (6)
C50.0185 (7)0.0189 (7)0.0237 (8)0.0032 (5)0.0021 (6)0.0019 (6)
C60.0302 (9)0.0184 (7)0.0177 (7)0.0015 (6)0.0025 (6)0.0020 (5)
C70.0193 (7)0.0194 (6)0.0183 (7)0.0015 (5)0.0009 (6)0.0001 (5)
C80.0259 (9)0.0199 (7)0.0240 (8)0.0010 (6)0.0002 (6)0.0024 (6)
C90.0408 (11)0.0314 (9)0.0257 (9)0.0055 (8)0.0081 (9)0.0019 (7)
Geometric parameters (Å, º) top
O1—C71.331 (2)C3—C41.417 (2)
O1—C81.464 (2)C4—C51.361 (2)
O2—C71.203 (2)C4—H40.9500
N1—C11.355 (2)C5—H50.9500
N1—C51.356 (2)C6—C71.515 (2)
N1—C61.460 (2)C6—H6A0.9900
N2—C31.333 (2)C6—H6B0.9900
N2—H210.85 (3)C8—C91.495 (3)
N2—H220.79 (3)C8—H8A0.9900
C1—C21.359 (3)C8—H8B0.9900
C1—H10.9500C9—H9A0.9800
C2—C31.417 (2)C9—H9B0.9800
C2—H20.9500C9—H9C0.9800
C7—O1—C8115.45 (14)N1—C6—C7111.30 (13)
C1—N1—C5119.58 (15)N1—C6—H6A109.4
C1—N1—C6120.25 (15)C7—C6—H6A109.4
C5—N1—C6120.17 (14)N1—C6—H6B109.4
C3—N2—H21119.2 (17)C7—C6—H6B109.4
C3—N2—H22117.1 (19)H6A—C6—H6B108.0
H21—N2—H22121 (3)O2—C7—O1125.64 (16)
N1—C1—C2121.84 (16)O2—C7—C6124.57 (16)
N1—C1—H1119.1O1—C7—C6109.74 (14)
C2—C1—H1119.1O1—C8—C9107.21 (15)
C1—C2—C3120.04 (16)O1—C8—H8A110.3
C1—C2—H2120.0C9—C8—H8A110.3
C3—C2—H2120.0O1—C8—H8B110.3
N2—C3—C2121.66 (16)C9—C8—H8B110.3
N2—C3—C4121.56 (16)H8A—C8—H8B108.5
C2—C3—C4116.76 (16)C8—C9—H9A109.5
C5—C4—C3120.19 (16)C8—C9—H9B109.5
C5—C4—H4119.9H9A—C9—H9B109.5
C3—C4—H4119.9C8—C9—H9C109.5
N1—C5—C4121.56 (15)H9A—C9—H9C109.5
N1—C5—H5119.2H9B—C9—H9C109.5
C4—C5—H5119.2
C5—N1—C1—C20.7 (3)C3—C4—C5—N11.4 (3)
C6—N1—C1—C2179.43 (17)C1—N1—C6—C7103.91 (18)
N1—C1—C2—C30.7 (3)C5—N1—C6—C775.9 (2)
C1—C2—C3—N2178.11 (18)C8—O1—C7—O29.8 (3)
C1—C2—C3—C40.3 (2)C8—O1—C7—C6167.70 (14)
N2—C3—C4—C5177.11 (17)N1—C6—C7—O220.9 (3)
C2—C3—C4—C51.3 (2)N1—C6—C7—O1161.57 (14)
C1—N1—C5—C40.3 (3)C7—O1—C8—C9177.72 (16)
C6—N1—C5—C4179.52 (16)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H21···I10.85 (3)2.79 (3)3.6384 (17)173 (2)
N2—H22···I1i0.79 (3)2.91 (2)3.6527 (17)159 (2)
Symmetry code: (i) x+1/2, y1/2, z.
 

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