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Journal logoSTRUCTURAL
CHEMISTRY
ISSN: 2053-2296

N-Benzyl­ethyl­ammonium nitrate: a three-dimensional hydrogen-bonded framework comprising substructures in zero, one and two dimensions

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aGrupo de Investigación de Compuestos Heterocíclicos, Departamento de Química, Universidad de Valle, AA 25360 Cali, Colombia, bDepartamento de Química Inorgánica y Orgánica, Universidad de Jaén, 23071 Jaén, Spain, cDepartment of Chemistry, University of Aberdeen, Meston Walk, Old Aberdeen AB24 3UE, Scotland, and dSchool of Chemistry, University of St Andrews, Fife KY16 9ST, Scotland
*Correspondence e-mail: cg@st-andrews.ac.uk

(Received 3 October 2005; accepted 5 October 2005; online 22 October 2005)

The title compound is a salt, C9H14N+·NO3, in which two N—H⋯O hydrogen bonds and two C—H⋯O hydrogen bonds generate a three-dimensional framework structure. The combination of one N—H⋯O hydrogen bond and one C—H⋯O hydrogen bond generates a finite (zero-dimensional) centrosymmetric R44(14) aggregate containing two cations and two anions; the combination of the two N—H⋯O hydrogen bonds generates a one-dimensional C22(6) chain of alternating cations and anions, and the combination of one N—H⋯O hydrogen bond and two C—H⋯O hydrogen bonds generates a two-dimensional sheet of alternating R44(14) and R86(34) rings.

Comment

In an attempt to effect the selective removal of the benzotriazole residue from N-(benzotriazol-1-yl­meth­yl)-N-ethyl­benzyl­amine, a methanol solution of this compound was treated at room temperature with an aqueous solution of silver nitrate, resulting in the formation of N-benz­yl­ethyl­ammonium nitrate, (I)[link], as the main isolated product.

[Scheme 1]

The two ionic components are linked into a three-dimensional framework structure of some complexity by a combination of two rather short N—H⋯O hydrogen bonds, between cationic N and anionic O atoms, and two C—H⋯O hydrogen bonds (Table 2[link]). The formation of the framework is readily analysed in terms of several fairly simple and low-dimensional substructures (Gregson et al., 2000[Gregson, R. M., Glidewell, C., Ferguson, G. & Lough, A. J. (2000). Acta Cryst. B56, 39-57.]). A one-dimensional substructure is built from N—H⋯O hydrogen bonds only, while a combination of one each of the N—H⋯O and C—H⋯O hydrogen bonds generates a finite zero-dimensional substructure, which itself forms the building block of a two-dimensional substructure utilizing one N—H⋯O hydrogen bond and both of the C—H⋯O hydrogen bonds.

Within the selected asymmetric unit (Fig. 1[link]), atom N2 in the cation acts as a hydrogen-bond donor, via H2A, to atom O1 in the anion. In addition, atom N2 in the cation at (x, y, z) acts as a donor, via H2B, to atom O3 in the anion at (−1 + x, y, z), so generating by translation a one-dimensional substructure in the form of a C22(6) (Bernstein et al., 1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]) chain running parallel to the [100] direction (Fig. 2[link]).

The action of the C—H⋯O hydrogen bonds leads to considerably more complexity than the rather simple motif generated by the N—H⋯O hydrogen bonds alone. However, the analysis of the two-dimensional substructure is markedly eased by the identification of a finite centrosymmetric four-ion aggregate. Atom C1 in the cation at (x, y, z), which is adjacent to the positive ammonium centre, acts as a hydrogen-bond donor, via H1A, to atom O3 in the anion at (1 − x, 1 − y, 1 − z), so forming by inversion a cyclic centrosymmetric R44(14) aggregate containing two cations and two anions and centred at ([{1\over 2}], [{1\over 2}], [{1\over 2}]) (Fig. 3[link]); this aggregate forms the basic building block for the construction of the two-dimensional substructure.

Aryl atoms C13 in the cations at (x, y, z) and (1 − x, 1 − y, 1 − z), which lie in the R44(14) aggregate centred at ([{1\over 2}], [{1\over 2}], [{1\over 2}]), act as hydrogen-bond donors, respectively, to atom O3 in the anions at (−[{1\over 2}] + x, [{3\over 2}]y, [{1\over 2}] + z) and ([{3\over 2}]x, −[{1\over 2}] + y, [{1\over 2}]z), which themselves lie in the R44(14) aggregates centred at (0, 1, 1) and (1, 0, 0), respectively. Similarly, atoms O3 in the anions at (xyz) and (1 − x, 1 − y, 1 − z) accept hydrogen bonds from atoms C13 in the cations at ([{1\over 2}] + x, [{3\over 2}]y, −[{1\over 2}] + z) and ([{1\over 2}] − x, −[{1\over 2}] + y, [{3\over 2}] − z), which form parts, respectively, of the R44(14) aggregates centred at (1, 1, 0) and (0, 0, 1). Propagation by the space group of this single hydrogen bond then links each R44(14) aggregate to four others, so forming a (101) sheet containing alternating R44(14) and R86(34) rings (Fig. 4[link]).

The combination of the [100] chain and the (101) sheet is sufficient to generate a continuous three-dimensional framework, within which it is possible to identify substructures in zero (Fig. 3[link]), one (Fig. 2[link]) and two (Fig. 4[link]) dimensions.

The conformation of the cation is unexpected. While the C1—N2 and C3—C4 bonds are antiperiplanar, the N2—C3 and C1—C11 bonds are synclinal (Table 1[link]); the aryl ring is approximately normal to the C11—C1—N2 plane. In the anion, it is notable that the N1—O2 bond is significantly shorter than the other two N—O bonds (Table 1[link]); in this respect, it is worth noting that atom O2 is the one O atom not involved in the hydrogen bonding. Associated with the unequal bond lengths, the O1—N2—O3 angle is significantly less than the other two O—N—O angles.

[Figure 1]
Figure 1
The independent components of (I)[link], showing the atom-labelling scheme and the N—H⋯O hydrogen bond (dashed lines) within the asymmetric unit. Displacement ellipsoids are drawn at the 30% probability level.
[Figure 2]
Figure 2
Part of the crystal structure of (I)[link], showing the formation of a hydrogen-bonded C22(6) chain along [100]. For clarity, H atoms bonded to C atoms have been omitted. Atoms marked with an asterisk (*) or a hash (#) are at the symmetry positions (−1 + x, y, z) and (1 + x, y, z), respectively.
[Figure 3]
Figure 3
Part of the crystal structure of (I)[link], showing the formation of a cyclic hydrogen-bonded R44(14) aggregate of two cations and two anions. For clarity, H atoms in the ethyl and phenyl groups have been omitted. Atoms marked with an asterisk (*) are at the symmetry position (1 − x, 1 − y, 1 − z).
[Figure 4]
Figure 4
A stereoview of part of the crystal structure of (I)[link], showing the formation of a hydrogen-bonded (101) sheet built from R44(14) and R86(34) rings. For clarity, H atoms not involved in the motifs shown have been omitted.

Experimental

An aqueous solution of AgNO3 (0.5 ml containing 0.44 mmol) was added dropwise at room temperature over a period of 5 min to a vigorously stirred solution of N-(benzo­triazol-1-yl­meth­yl)-N-ethyl-benzyl­amine (0.1 g, 0.38 mmol) in methanol (5 ml). The resulting precipitate was removed by filtration and the filtrate was evaporated under reduced pressure, yielding an oily residue. After two days, colourless crystals of (I)[link] had formed from the oil, and these proved to be suitable for single-crystal X-ray diffraction (90% yield; m.p. 368–369 K). MS: (70 eV) m/z (%) 136 (21.5, M+), 120 (26.5), 91 (100).

Crystal data
  • C9H14N+·NO3

  • Mr = 198.22

  • Monoclinic, P 21 /n

  • a = 5.9538 (4) Å

  • b = 8.9940 (6) Å

  • c = 18.7484 (8) Å

  • β = 98.324 (4)°

  • V = 993.37 (10) Å3

  • Z = 4

  • Dx = 1.325 Mg m−3

  • Mo Kα radiation

  • Cell parameters from 2262 reflections

  • θ = 3.2–27.5°

  • μ = 0.10 mm−1

  • T = 120 (2) K

  • Block, colourless

  • 0.50 × 0.30 × 0.20 mm

Data collection
  • Nonius KappaCCD diffractometer

  • φ and ω scans

  • Absorption correction: multi-scan(SADABS; Sheldrick, 2003[Sheldrick, G. M. (2003). SADABS. Version 2.10. University of Göttingen, Germany.])Tmin = 0.969, Tmax = 0.980

  • 13128 measured reflections

  • 2262 independent reflections

  • 1869 reflections with I > 2σ(I)

  • Rint = 0.036

  • θmax = 27.5°

  • h = −7 → 7

  • k = −11 → 11

  • l = −24 → 22

Refinement
  • Refinement on F2

  • R[F2 > 2σ(F2)] = 0.043

  • wR(F2) = 0.132

  • S = 1.11

  • 2262 reflections

  • 128 parameters

  • H-atom parameters constrained

  • w = 1/[σ2(Fo2) + (0.0781P)2 + 0.2024P] where P = (Fo2 + 2Fc2)/3

  • (Δ/σ)max < 0.001

  • Δρmax = 0.23 e Å−3

  • Δρmin = −0.30 e Å−3

Table 1
Selected geometric parameters (Å, °)[link]

N1—O1 1.2601 (15)
N1—O2 1.2404 (15)
N1—O3 1.2603 (14)
O1—N1—O2 120.60 (11)
O2—N1—O3 120.54 (11)
O1—N1—O3 118.85 (11)
C12—C11—C1—N2 100.66 (14)
C11—C1—N2—C3 −74.31 (14)
C1—N2—C3—C4 173.25 (11)

Table 2
Hydrogen-bond geometry (Å, °)[link]

D—H⋯A D—H H⋯A DA D—H⋯A
N2—H2A⋯O1 0.92 1.99 2.8855 (15) 164
N2—H2B⋯O3i 0.92 1.93 2.8299 (15) 166
C1—H1A⋯O3ii 0.99 2.48 3.2652 (17) 136
C13—H13⋯O3iii 0.95 2.52 3.4050 (17) 156
Symmetry codes: (i) x-1, y, z; (ii) -x+1, -y+1, -z+1; (iii) [x-{\script{1\over 2}}, -y+{\script{3\over 2}}, z+{\script{1\over 2}}].

The space group P21/n was uniquely assigned from the systematic absences. All H atoms were located from difference maps and then treated as riding atoms, with C—H distances of 0.95 (aromatic), 0.98 (CH3) or 0.99 Å (CH2), and N—H distances of 0.92 Å, and with Uiso(H) values of 1.2Ueq(C,N) or 1.5Ueq(methyl C).

Data collection: COLLECT (Hooft, 1999[Hooft, R. W. W. (1999). COLLECT. Nonius BV, Delft, The Netherlands.]); cell refinement: DENZO (Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.]) and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: OSCAIL (McArdle, 2003[McArdle, P. (2003). OSCAIL for Windows. Version 10. Crystallography Centre, Chemistry Department, NUI Galway, Ireland.]) and SHELXS97 (Sheldrick, 1997[Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany.]); program(s) used to refine structure: OSCAIL and SHELXL97 (Sheldrick, 1997[Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany.]); molecular graphics: PLATON (Spek, 2003[Spek, A. L. (2003). J. Appl. Cryst. 36, 7-13.]); software used to prepare material for publication: SHELXL97 and PRPKAPPA (Ferguson, 1999[Ferguson, G. (1999). PRPKAPPA. University of Guelph, Canada.]).

Supporting information


Comment top

In an attempt to effect the selective removal of the benzotriazole residue from N-(benzotriazol-1-ylmethyl)-N-ethylbenzylamine, a methanol solution of this compound was treated at room temperature with an aqueous solution of silver nitrate, resulting in the formation of (N-benzyl)ethylammonium nitrate (I) as the main isolated product.

The two ionic components are linked into a three-dimensional framework structure of some complexity by a combination of two rather short N—H···O hydrogen bonds, between cationic N and anionic O atoms, and two C—H···O hydrogen bonds (Table 2). The formation of the framework is readily analysed in terms of several fairly simple and low-dimensional substructures (Gregson et al., 2000); a one dimensional substructure is built from N—H···O hydrogen bonds only, while a combination of one each of the N—H···O and C—H···O hydrogen bonds generates a finite zero-dimensional substructure, which itself forms the building block of a two-dimensional substructure utilizing one N—H···O hydrogen bond and both of the C—H···O hydrogen bonds.

Within the selected asymmetric unit (Fig. 1), atom N2 in the cation acts as a hydrogen-bond donor, via H2A, to atom O1 in the anion. In addition, atom N2 in the cation at (x, y, z) acts as a donor, via H2B, to atom O3 in the anion at (−1 + x, y, z), so generating by translation a one-dimensional substructure in the form of a C22(6) (Bernstein et al., 1995) chain running parallel to the [100] direction (Fig. 2).

The action of the C—H···O hydrogen bonds leads to considerably more complexity than the rather simple motif generated by the N—H···O hydrogen bonds alone. However, the analysis of the two-dimensional substructure is markedly eased by the identification of a finite centrosymmetric four-ion aggregate. Atom C1 in the cation at (x, y, z), which is adjacent to the positive ammonium centre, acts as a hydrogen-bond donor, via H1A, to atom O3 in the anion at (1 − x, 1 − y, 1 − z), so forming by inversion a cyclic centrosymmetric R44(14) aggregate containing two cations and two anions and centred at (1/2, 1/2, 1/2) (Fig. 3); this aggregate forms the basic building block for the construction of the two-dimensional substructure.

The aryl atoms C13 in the two cations at (x, y, z) and (1 − x, 1 − y, 1 − z), which lie in the R44(14) aggregate centred at (1/2, 1/2, 1/2), act as hydrogen-bond donors, respectively, to atom O3 in the anions at (−1/2 + x, 3/2 − y, 1/2 + z) and (3/2 − x, −1/2 + y, 1/2 − z), which themselves lie in the R44(14) aggregates centred at (0, 1, 1) and (1, 0, 0), respectively. Similarly, atoms O3 in the anions at (x, y, z) and (1 − x, 1 − y, 1 − z) accept hydrogen bonds from atoms C13 in the cations at (1/2 + x, 3/2 − y, −1/2 + z) and (1/2 − x, −1/2 + y, 3/2 − z), which form parts, respectively, of the R44(14) aggregates centred at (1, 1, 0) and (0, 0, 1). Propagation by the space group of this single hydrogen bond then links each R44(14) aggregate to four others, so forming a (101) sheet containing alternating R44(14) and R68(34) rings (Fig. 4).

The combination of the [100] chain and the (101) sheet is sufficient to generate a continuous three-dimensional framework, within which it is possible to identify substructures in zero (Fig. 3), one (Fig. 2) and two (Fig. 4) dimensions.

The conformation of the cation is unexpected. While the C1—N2 and C3—C4 bonds are antiperiplanar, the N2—C3 and C1—C11 bonds are synclinal (Table 1): the aryl ring is approximately normal to the C11—C1—N2 plane. In the anion, it is notable that the N1—O2 bond is significantly shorter than the other two N—O bonds (Table 1); in this respect it is worth noting that atom O2 is the one O atom not involved in the hydrogen bonding. Associated with the unequal bond lengths, the O1—N2—O3 angle is significantly less than the other two O—N—O angles.

Experimental top

An aqueous solution of AgNO3 (0.5 ml containing 0.44 mmol) was added dropwise at room temperature over a period of 5 min to a vigorously stirred solution of N-ethyl-N-(benzotriazol-1-ylmethyl)benzylamine (0.1 g, 0.38 mmol) in methanol (5 ml). The resulting precipitate was removed by filtration and the filtrate was evaporated under reduced pressure, yielding an oily residue. After two days, colourless crystals of the title compound, (I), were formed from the oil, and these proved to be suitable for single-crystal X-ray diffraction (90% yield; m.p. 368–369 K). MS: (70 eV) m/z (%) 136 (21.5, M+), 120 (26.5), 91 (100).

Refinement top

The space group P21/n was uniquely assigned from the systematic absences. All H atoms were located from difference maps and then treated as riding atoms, with C—H distances 0.95 Å (aromatic), 0.98 Å (CH3) or 0.99 Å (CH2), and N—H distamces of 0.92 Å, and with Uiso(H) values of 1.2Ueq(C,N), or 1.5Ueq(C) for the methyl group.

Computing details top

Data collection: COLLECT (Hooft, 1999); cell refinement: DENZO (Otwinowski & Minor, 1997) and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: OSCAIL (McArdle, 2003) and SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: OSCAIL and SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 and PRPKAPPA (Ferguson, 1999).

Figures top
[Figure 1] Fig. 1. The independent components of (I), showing the atom-labelling scheme, and the N—H···O hydrogen bond (dashed lines) within the asymmetric unit. Displacement ellipsoids are drawn at the 30% probability level.
[Figure 2] Fig. 2. Part of the crystal structure of (I), showing the formation of a hydrogen-bonded C22(6) chain along [100]. For clarity, H atoms bonded to C atoms have been omitted. The atoms marked with an asterisk (*) or a hash (#) are at the symmetry positions (−1 + x, y, z) and (1 + x, y, z), respectively.
[Figure 3] Fig. 3. Part of the crystal structure of (I), showing the formation of a cyclic hydrogen-bonded R44(14) aggregate of two cations and two anions. For clarity, H atoms in the ethyl and phenyl groups have been omitted. The atoms marked with an asterisk (*) are at the symmetry position (1 − x, 1 − y, 1 − z).
[Figure 4] Fig. 4. A stereoview of part of the crystal structure of (I), showing the formation of a hydrogen-bonded (101) sheet built from R44(14) and R68(34) rings. For clarity, H atoms not involved in the motifs shown have been omitted.
N-Benzylethylammonium nitrate top
Crystal data top
C9H14N+·NO3F(000) = 424
Mr = 198.22Dx = 1.325 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 2262 reflections
a = 5.9538 (4) Åθ = 3.2–27.5°
b = 8.9940 (6) ŵ = 0.10 mm1
c = 18.7484 (8) ÅT = 120 K
β = 98.324 (4)°Block, colourless
V = 993.37 (10) Å30.50 × 0.30 × 0.20 mm
Z = 4
Data collection top
Nonius KappaCCD
diffractometer
2262 independent reflections
Radiation source: Bruker-Nonius FR91 rotating anode1869 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.036
Detector resolution: 9.091 pixels mm-1θmax = 27.5°, θmin = 3.2°
ϕ and ω scansh = 77
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)
k = 1111
Tmin = 0.969, Tmax = 0.980l = 2422
13128 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.043Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.132H-atom parameters constrained
S = 1.11 w = 1/[σ2(Fo2) + (0.0781P)2 + 0.2024P]
where P = (Fo2 + 2Fc2)/3
2262 reflections(Δ/σ)max < 0.001
128 parametersΔρmax = 0.23 e Å3
0 restraintsΔρmin = 0.30 e Å3
Crystal data top
C9H14N+·NO3V = 993.37 (10) Å3
Mr = 198.22Z = 4
Monoclinic, P21/nMo Kα radiation
a = 5.9538 (4) ŵ = 0.10 mm1
b = 8.9940 (6) ÅT = 120 K
c = 18.7484 (8) Å0.50 × 0.30 × 0.20 mm
β = 98.324 (4)°
Data collection top
Nonius KappaCCD
diffractometer
2262 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)
1869 reflections with I > 2σ(I)
Tmin = 0.969, Tmax = 0.980Rint = 0.036
13128 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0430 restraints
wR(F2) = 0.132H-atom parameters constrained
S = 1.11Δρmax = 0.23 e Å3
2262 reflectionsΔρmin = 0.30 e Å3
128 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N20.21428 (19)0.68498 (12)0.59403 (6)0.0194 (3)
C10.1709 (2)0.58878 (15)0.65603 (7)0.0225 (3)
C30.1935 (2)0.84726 (15)0.60812 (7)0.0230 (3)
C40.2662 (3)0.93844 (16)0.54747 (8)0.0274 (3)
C110.3662 (2)0.59259 (14)0.71688 (7)0.0195 (3)
C120.3581 (2)0.68007 (15)0.77790 (7)0.0225 (3)
C130.5422 (3)0.68509 (16)0.83270 (7)0.0257 (3)
C140.7341 (2)0.60175 (17)0.82751 (7)0.0273 (3)
C150.7415 (2)0.51115 (17)0.76770 (7)0.0269 (3)
C160.5593 (2)0.50718 (15)0.71266 (7)0.0234 (3)
N10.67586 (19)0.66128 (12)0.50171 (6)0.0203 (3)
O10.68052 (16)0.68272 (12)0.56832 (5)0.0253 (3)
O20.49243 (17)0.65449 (12)0.46095 (5)0.0299 (3)
O30.86091 (16)0.64795 (12)0.47709 (5)0.0275 (3)
H1A0.14550.48510.63910.027*
H1B0.03130.62320.67400.027*
H2A0.35800.66590.58380.023*
H2B0.11300.65980.55400.023*
H3A0.28940.87330.65400.028*
H3B0.03400.87110.61290.028*
H4A0.42690.91960.54470.041*
H4B0.24431.04430.55670.041*
H4C0.17460.91040.50180.041*
H120.22590.73660.78200.027*
H130.53600.74590.87380.031*
H140.86070.60630.86470.033*
H150.87180.45190.76460.032*
H160.56590.44580.67180.028*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N20.0182 (5)0.0226 (6)0.0175 (6)0.0014 (4)0.0028 (4)0.0001 (4)
C10.0217 (7)0.0252 (7)0.0205 (7)0.0050 (5)0.0024 (5)0.0035 (5)
C30.0249 (7)0.0215 (7)0.0227 (7)0.0012 (5)0.0038 (5)0.0017 (5)
C40.0294 (8)0.0242 (7)0.0284 (8)0.0002 (6)0.0033 (6)0.0040 (5)
C110.0206 (7)0.0196 (6)0.0186 (6)0.0024 (5)0.0038 (5)0.0033 (5)
C120.0261 (7)0.0213 (7)0.0210 (7)0.0027 (5)0.0065 (5)0.0014 (5)
C130.0361 (8)0.0228 (7)0.0180 (7)0.0022 (6)0.0030 (6)0.0004 (5)
C140.0269 (7)0.0327 (8)0.0210 (7)0.0030 (6)0.0009 (5)0.0056 (6)
C150.0223 (7)0.0340 (8)0.0250 (7)0.0058 (6)0.0058 (6)0.0057 (6)
C160.0274 (7)0.0237 (7)0.0201 (7)0.0022 (5)0.0071 (5)0.0002 (5)
N10.0195 (6)0.0205 (6)0.0203 (6)0.0008 (4)0.0012 (4)0.0002 (4)
O10.0220 (5)0.0372 (6)0.0165 (5)0.0004 (4)0.0023 (4)0.0028 (4)
O20.0226 (5)0.0397 (6)0.0248 (5)0.0008 (4)0.0054 (4)0.0018 (4)
O30.0221 (5)0.0384 (6)0.0232 (5)0.0002 (4)0.0068 (4)0.0024 (4)
Geometric parameters (Å, º) top
C1—N21.5013 (16)C11—C121.3950 (18)
C1—C111.5068 (18)C12—C131.390 (2)
C1—H1A0.99C12—H120.95
C1—H1B0.99C13—C141.382 (2)
N2—C31.4915 (17)C13—H130.95
N2—H2A0.92C14—C151.392 (2)
N2—H2B0.92C14—H140.95
C3—C41.5152 (19)C15—C161.385 (2)
C3—H3A0.99C15—H150.95
C3—H3B0.99C16—H160.95
C4—H4A0.98N1—O11.2601 (15)
C4—H4B0.98N1—O21.2404 (15)
C4—H4C0.98N1—O31.2603 (14)
C11—C161.3944 (19)
N2—C1—C11111.88 (10)H4B—C4—H4C109.5
N2—C1—H1A109.2C16—C11—C12118.92 (12)
C11—C1—H1A109.2C16—C11—C1119.79 (12)
N2—C1—H1B109.2C12—C11—C1121.29 (12)
C11—C1—H1B109.2C13—C12—C11120.49 (13)
H1A—C1—H1B107.9C13—C12—H12119.8
C3—N2—C1113.50 (10)C11—C12—H12119.8
C3—N2—H2A108.9C14—C13—C12120.13 (13)
C1—N2—H2A108.9C14—C13—H13119.9
C3—N2—H2B108.9C12—C13—H13119.9
C1—N2—H2B108.9C13—C14—C15119.80 (13)
H2A—N2—H2B107.7C13—C14—H14120.1
N2—C3—C4110.90 (11)C15—C14—H14120.1
N2—C3—H3A109.5C16—C15—C14120.18 (13)
C4—C3—H3A109.5C16—C15—H15119.9
N2—C3—H3B109.5C14—C15—H15119.9
C4—C3—H3B109.5C15—C16—C11120.46 (13)
H3A—C3—H3B108.0C15—C16—H16119.8
C3—C4—H4A109.5C11—C16—H16119.8
C3—C4—H4B109.5O1—N1—O2120.60 (11)
H4A—C4—H4B109.5O2—N1—O3120.54 (11)
C3—C4—H4C109.5O1—N1—O3118.85 (11)
H4A—C4—H4C109.5
C12—C11—C1—N2100.66 (14)C11—C12—C13—C140.8 (2)
C11—C1—N2—C374.31 (14)C12—C13—C14—C150.9 (2)
C1—N2—C3—C4173.25 (11)C13—C14—C15—C161.6 (2)
N2—C1—C11—C1679.46 (15)C14—C15—C16—C110.6 (2)
C16—C11—C12—C131.7 (2)C12—C11—C16—C151.0 (2)
C1—C11—C12—C13178.38 (12)C1—C11—C16—C15179.08 (12)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2A···O10.921.992.8855 (15)164
N2—H2B···O3i0.921.932.8299 (15)166
C1—H1A···O3ii0.992.483.2652 (17)136
C13—H13···O3iii0.952.523.4050 (17)156
Symmetry codes: (i) x1, y, z; (ii) x+1, y+1, z+1; (iii) x1/2, y+3/2, z+1/2.

Experimental details

Crystal data
Chemical formulaC9H14N+·NO3
Mr198.22
Crystal system, space groupMonoclinic, P21/n
Temperature (K)120
a, b, c (Å)5.9538 (4), 8.9940 (6), 18.7484 (8)
β (°) 98.324 (4)
V3)993.37 (10)
Z4
Radiation typeMo Kα
µ (mm1)0.10
Crystal size (mm)0.50 × 0.30 × 0.20
Data collection
DiffractometerNonius KappaCCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 2003)
Tmin, Tmax0.969, 0.980
No. of measured, independent and
observed [I > 2σ(I)] reflections
13128, 2262, 1869
Rint0.036
(sin θ/λ)max1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.043, 0.132, 1.11
No. of reflections2262
No. of parameters128
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.23, 0.30

Computer programs: COLLECT (Hooft, 1999), DENZO (Otwinowski & Minor, 1997) and COLLECT, DENZO and COLLECT, OSCAIL (McArdle, 2003) and SHELXS97 (Sheldrick, 1997), OSCAIL and SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2003), SHELXL97 and PRPKAPPA (Ferguson, 1999).

Selected geometric parameters (Å, º) top
N1—O11.2601 (15)N1—O31.2603 (14)
N1—O21.2404 (15)
O1—N1—O2120.60 (11)O1—N1—O3118.85 (11)
O2—N1—O3120.54 (11)
C12—C11—C1—N2100.66 (14)C1—N2—C3—C4173.25 (11)
C11—C1—N2—C374.31 (14)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2A···O10.921.992.8855 (15)164
N2—H2B···O3i0.921.932.8299 (15)166
C1—H1A···O3ii0.992.483.2652 (17)136
C13—H13···O3iii0.952.523.4050 (17)156
Symmetry codes: (i) x1, y, z; (ii) x+1, y+1, z+1; (iii) x1/2, y+3/2, z+1/2.
 

Acknowledgements

X-ray data were collected at the EPSRC X-ray Crystallographic Service, University of Southampton, England. JC thanks the Consejería de Innovación, Ciencia y Empresa (Junta de Andalucía, Spain) and the Universidad de Jaén for financial support. RA and ER thank COLCIENCIAS and UNIVALLE (Universidad del Valle, Colombia) for financial support.

References

First citationBernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573.  CrossRef CAS Web of Science Google Scholar
First citationFerguson, G. (1999). PRPKAPPA. University of Guelph, Canada.  Google Scholar
First citationGregson, R. M., Glidewell, C., Ferguson, G. & Lough, A. J. (2000). Acta Cryst. B56, 39–57.  Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
First citationHooft, R. W. W. (1999). COLLECT. Nonius BV, Delft, The Netherlands.  Google Scholar
First citationMcArdle, P. (2003). OSCAIL for Windows. Version 10. Crystallography Centre, Chemistry Department, NUI Galway, Ireland.  Google Scholar
First citationOtwinowski, Z. & Minor, W (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307–326. New York: Academic Press.  Google Scholar
First citationSheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany.  Google Scholar
First citationSheldrick, G. M. (2003). SADABS. Version 2.10. University of Göttingen, Germany.  Google Scholar
First citationSpek, A. L. (2003). J. Appl. Cryst. 36, 7–13.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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