The crystal structure of the title compound, C
9H
13N
2O
2+·I
−, consists of pyridinium cations and iodide anions stabilized by intermolecular N—H
I hydrogen bonds, forming one-dimensional chains along [010].
Supporting information
CCDC reference: 610850
Key indicators
- Single-crystal X-ray study
- T = 115 K
- Mean (C-C)= 0.002 Å
- R factor = 0.028
- wR factor = 0.068
- Data-to-parameter ratio = 41.0
checkCIF/PLATON results
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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+·I− | F(000) = 1200 |
Mr = 308.11 | Dx = 1.738 Mg m−3 |
Orthorhombic, Pbcn | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2n 2ab | Cell parameters from 5877 reflections |
a = 12.5402 (15) Å | θ = 2.5–36.3° |
b = 9.8173 (10) Å | µ = 2.70 mm−1 |
c = 19.135 (2) Å | T = 115 K |
V = 2355.7 (4) Å3 | Fragment, colorless |
Z = 8 | 0.25 × 0.22 × 0.20 mm |
Data collection top
Bruker–Nonius KappaCCD diffractometer | 5535 independent reflections |
Radiation source: fine-focus sealed tube | 4300 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.021 |
ω scans with κ offsets | θmax = 36.4°, θmin = 2.6° |
Absorption correction: multi-scan (SCALEPACK; Otwinowski & Minor, 1997) | h = −20→20 |
Tmin = 0.524, Tmax = 0.583 | k = −16→16 |
36052 measured reflections | l = −31→31 |
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)] = 0.028 | H 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 reflections | Δρmax = 1.37 e Å−3 |
135 parameters | Δρmin = −0.96 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: 0.00249 (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 | x | y | z | Uiso*/Ueq | |
I1 | 0.405389 (9) | 0.986511 (11) | 0.362361 (7) | 0.02060 (4) | |
O1 | 0.39560 (10) | 0.55695 (13) | 0.81826 (7) | 0.0223 (2) | |
O2 | 0.33509 (11) | 0.45961 (13) | 0.71919 (7) | 0.0230 (2) | |
N1 | 0.28417 (12) | 0.71539 (13) | 0.66589 (7) | 0.0182 (2) | |
N2 | 0.22075 (15) | 0.76726 (17) | 0.45649 (9) | 0.0271 (3) | |
H21 | 0.264 (2) | 0.813 (3) | 0.4314 (13) | 0.033* | |
H22 | 0.178 (2) | 0.718 (2) | 0.4394 (13) | 0.033* | |
C1 | 0.35218 (15) | 0.78728 (17) | 0.62508 (10) | 0.0217 (3) | |
H1 | 0.4143 | 0.8258 | 0.6455 | 0.026* | |
C2 | 0.33407 (14) | 0.80583 (17) | 0.55571 (9) | 0.0218 (3) | |
H2 | 0.3828 | 0.8576 | 0.5285 | 0.026* | |
C3 | 0.24258 (13) | 0.74801 (16) | 0.52394 (9) | 0.0193 (3) | |
C4 | 0.17390 (14) | 0.67153 (17) | 0.56777 (9) | 0.0208 (3) | |
H4 | 0.1123 | 0.6291 | 0.5487 | 0.025* | |
C5 | 0.19591 (14) | 0.65866 (17) | 0.63709 (9) | 0.0203 (3) | |
H5 | 0.1483 | 0.6087 | 0.6660 | 0.024* | |
C6 | 0.30583 (15) | 0.69873 (16) | 0.74035 (9) | 0.0221 (3) | |
H6A | 0.2395 | 0.7148 | 0.7672 | 0.027* | |
H6B | 0.3591 | 0.7672 | 0.7553 | 0.027* | |
C7 | 0.34749 (13) | 0.55725 (16) | 0.75628 (9) | 0.0190 (3) | |
C8 | 0.41984 (15) | 0.42220 (18) | 0.84688 (10) | 0.0233 (3) | |
H8A | 0.4700 | 0.3732 | 0.8158 | 0.028* | |
H8B | 0.3538 | 0.3676 | 0.8512 | 0.028* | |
C9 | 0.46905 (18) | 0.4435 (2) | 0.91722 (11) | 0.0326 (4) | |
H9A | 0.5376 | 0.4904 | 0.9119 | 0.049* | |
H9B | 0.4805 | 0.3551 | 0.9398 | 0.049* | |
H9C | 0.4213 | 0.4991 | 0.9461 | 0.049* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
I1 | 0.01526 (6) | 0.01929 (6) | 0.02726 (7) | −0.00075 (3) | −0.00035 (4) | 0.00264 (3) |
O1 | 0.0286 (7) | 0.0182 (5) | 0.0201 (6) | −0.0009 (5) | −0.0050 (5) | 0.0009 (4) |
O2 | 0.0283 (6) | 0.0188 (5) | 0.0218 (6) | 0.0003 (5) | −0.0017 (5) | −0.0027 (4) |
N1 | 0.0207 (6) | 0.0153 (5) | 0.0187 (6) | −0.0014 (5) | −0.0013 (5) | −0.0003 (4) |
N2 | 0.0320 (8) | 0.0288 (8) | 0.0205 (7) | −0.0078 (6) | −0.0009 (6) | 0.0015 (6) |
C1 | 0.0203 (8) | 0.0187 (7) | 0.0262 (8) | −0.0058 (6) | −0.0010 (6) | 0.0000 (6) |
C2 | 0.0210 (8) | 0.0203 (7) | 0.0241 (8) | −0.0069 (6) | 0.0016 (6) | 0.0018 (6) |
C3 | 0.0203 (7) | 0.0167 (6) | 0.0207 (7) | −0.0010 (5) | 0.0010 (6) | −0.0002 (5) |
C4 | 0.0181 (7) | 0.0206 (7) | 0.0237 (8) | −0.0040 (5) | −0.0016 (6) | 0.0008 (6) |
C5 | 0.0185 (7) | 0.0189 (7) | 0.0237 (8) | −0.0032 (5) | 0.0021 (6) | 0.0019 (6) |
C6 | 0.0302 (9) | 0.0184 (7) | 0.0177 (7) | 0.0015 (6) | −0.0025 (6) | −0.0020 (5) |
C7 | 0.0193 (7) | 0.0194 (6) | 0.0183 (7) | −0.0015 (5) | 0.0009 (6) | −0.0001 (5) |
C8 | 0.0259 (9) | 0.0199 (7) | 0.0240 (8) | 0.0010 (6) | −0.0002 (6) | 0.0024 (6) |
C9 | 0.0408 (11) | 0.0314 (9) | 0.0257 (9) | 0.0055 (8) | −0.0081 (9) | 0.0019 (7) |
Geometric parameters (Å, º) top
O1—C7 | 1.331 (2) | C3—C4 | 1.417 (2) |
O1—C8 | 1.464 (2) | C4—C5 | 1.361 (2) |
O2—C7 | 1.203 (2) | C4—H4 | 0.9500 |
N1—C1 | 1.355 (2) | C5—H5 | 0.9500 |
N1—C5 | 1.356 (2) | C6—C7 | 1.515 (2) |
N1—C6 | 1.460 (2) | C6—H6A | 0.9900 |
N2—C3 | 1.333 (2) | C6—H6B | 0.9900 |
N2—H21 | 0.85 (3) | C8—C9 | 1.495 (3) |
N2—H22 | 0.79 (3) | C8—H8A | 0.9900 |
C1—C2 | 1.359 (3) | C8—H8B | 0.9900 |
C1—H1 | 0.9500 | C9—H9A | 0.9800 |
C2—C3 | 1.417 (2) | C9—H9B | 0.9800 |
C2—H2 | 0.9500 | C9—H9C | 0.9800 |
| | | |
C7—O1—C8 | 115.45 (14) | N1—C6—C7 | 111.30 (13) |
C1—N1—C5 | 119.58 (15) | N1—C6—H6A | 109.4 |
C1—N1—C6 | 120.25 (15) | C7—C6—H6A | 109.4 |
C5—N1—C6 | 120.17 (14) | N1—C6—H6B | 109.4 |
C3—N2—H21 | 119.2 (17) | C7—C6—H6B | 109.4 |
C3—N2—H22 | 117.1 (19) | H6A—C6—H6B | 108.0 |
H21—N2—H22 | 121 (3) | O2—C7—O1 | 125.64 (16) |
N1—C1—C2 | 121.84 (16) | O2—C7—C6 | 124.57 (16) |
N1—C1—H1 | 119.1 | O1—C7—C6 | 109.74 (14) |
C2—C1—H1 | 119.1 | O1—C8—C9 | 107.21 (15) |
C1—C2—C3 | 120.04 (16) | O1—C8—H8A | 110.3 |
C1—C2—H2 | 120.0 | C9—C8—H8A | 110.3 |
C3—C2—H2 | 120.0 | O1—C8—H8B | 110.3 |
N2—C3—C2 | 121.66 (16) | C9—C8—H8B | 110.3 |
N2—C3—C4 | 121.56 (16) | H8A—C8—H8B | 108.5 |
C2—C3—C4 | 116.76 (16) | C8—C9—H9A | 109.5 |
C5—C4—C3 | 120.19 (16) | C8—C9—H9B | 109.5 |
C5—C4—H4 | 119.9 | H9A—C9—H9B | 109.5 |
C3—C4—H4 | 119.9 | C8—C9—H9C | 109.5 |
N1—C5—C4 | 121.56 (15) | H9A—C9—H9C | 109.5 |
N1—C5—H5 | 119.2 | H9B—C9—H9C | 109.5 |
C4—C5—H5 | 119.2 | | |
| | | |
C5—N1—C1—C2 | 0.7 (3) | C3—C4—C5—N1 | −1.4 (3) |
C6—N1—C1—C2 | −179.43 (17) | C1—N1—C6—C7 | −103.91 (18) |
N1—C1—C2—C3 | −0.7 (3) | C5—N1—C6—C7 | 75.9 (2) |
C1—C2—C3—N2 | 178.11 (18) | C8—O1—C7—O2 | −9.8 (3) |
C1—C2—C3—C4 | −0.3 (2) | C8—O1—C7—C6 | 167.70 (14) |
N2—C3—C4—C5 | −177.11 (17) | N1—C6—C7—O2 | −20.9 (3) |
C2—C3—C4—C5 | 1.3 (2) | N1—C6—C7—O1 | 161.57 (14) |
C1—N1—C5—C4 | 0.3 (3) | C7—O1—C8—C9 | −177.72 (16) |
C6—N1—C5—C4 | −179.52 (16) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H21···I1 | 0.85 (3) | 2.79 (3) | 3.6384 (17) | 173 (2) |
N2—H22···I1i | 0.79 (3) | 2.91 (2) | 3.6527 (17) | 159 (2) |
Symmetry code: (i) −x+1/2, y−1/2, z. |