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

Abonia, R.; Rengifo, E.; Cobo, J.; Low, J.N.; Glidewell, C.

doi:10.1107/S0108270105031719

organic compounds

STRUCTURAL
CHEMISTRY

ISSN: 2053-2296

Volume 61| Part 11| November 2005| Pages o645-o647

doi:10.1107/S0108270105031719

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

Rodrigo Abonia,^a Emerson Rengifo,^a Justo Cobo,^b John N. Low ^c and Christopher Glidewell ^d ^*

^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), 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 ( $[{1\over 2}]$ , $[{1\over 2}]$ , $[{1\over 2}]$ ) (Fig. 3); 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 (x, y, z) 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).

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.

Figure 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
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. 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
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. Atoms marked with an asterisk (*) are at the symmetry position (1 − x, 1 − y, 1 − z).

Figure 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 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) 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⁻
M_r = 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
D_x = 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 )T_min = 0.969, T_max = 0.980
13128 measured reflections
2262 independent reflections
1869 reflections with I > 2σ(I)
R_int = 0.036
θ_max = 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(F_o²) + (0.0781P)² + 0.2024P] where P = (F_o² + 2F_c²)/3
(Δ/σ)_max < 0.001
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.30 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

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, °)

D—H⋯A	D—H	H⋯A	D⋯A	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 U_iso(H) values of 1.2U_eq(C,N) or 1.5U_eq(methyl C).

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 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S0108270105031719/sk1877sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S0108270105031719/sk1877Isup2.hkl

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 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).

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

	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.
	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.
	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).
	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⁺·NO₃⁻	F(000) = 424
M_r = 198.22	D_x = 1.325 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2262 reflections
a = 5.9538 (4) Å	θ = 3.2–27.5°
b = 8.9940 (6) Å	µ = 0.10 mm⁻¹
c = 18.7484 (8) Å	T = 120 K
β = 98.324 (4)°	Block, colourless
V = 993.37 (10) Å³	0.50 × 0.30 × 0.20 mm
Z = 4

Data collection top

Nonius KappaCCD diffractometer	2262 independent reflections
Radiation source: Bruker-Nonius FR91 rotating anode	1869 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.036
Detector resolution: 9.091 pixels mm^-1	θ_max = 27.5°, θ_min = 3.2°
ϕ and ω scans	h = −7→7
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	k = −11→11
T_min = 0.969, T_max = 0.980	l = −24→22
13128 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.132	H-atom parameters constrained
S = 1.11	w = 1/[σ²(F_o²) + (0.0781P)² + 0.2024P] where P = (F_o² + 2F_c²)/3
2262 reflections	(Δ/σ)_max < 0.001
128 parameters	Δρ_max = 0.23 e Å⁻³
0 restraints	Δρ_min = −0.30 e Å⁻³

Crystal data top

C₉H₁₄N⁺·NO₃⁻	V = 993.37 (10) Å³
M_r = 198.22	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 5.9538 (4) Å	µ = 0.10 mm⁻¹
b = 8.9940 (6) Å	T = 120 K
c = 18.7484 (8) Å	0.50 × 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)
T_min = 0.969, T_max = 0.980	R_int = 0.036
13128 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.043	0 restraints
wR(F²) = 0.132	H-atom parameters constrained
S = 1.11	Δρ_max = 0.23 e Å⁻³
2262 reflections	Δρ_min = −0.30 e Å⁻³
128 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
N2	0.21428 (19)	0.68498 (12)	0.59403 (6)	0.0194 (3)
C1	0.1709 (2)	0.58878 (15)	0.65603 (7)	0.0225 (3)
C3	0.1935 (2)	0.84726 (15)	0.60812 (7)	0.0230 (3)
C4	0.2662 (3)	0.93844 (16)	0.54747 (8)	0.0274 (3)
C11	0.3662 (2)	0.59259 (14)	0.71688 (7)	0.0195 (3)
C12	0.3581 (2)	0.68007 (15)	0.77790 (7)	0.0225 (3)
C13	0.5422 (3)	0.68509 (16)	0.83270 (7)	0.0257 (3)
C14	0.7341 (2)	0.60175 (17)	0.82751 (7)	0.0273 (3)
C15	0.7415 (2)	0.51115 (17)	0.76770 (7)	0.0269 (3)
C16	0.5593 (2)	0.50718 (15)	0.71266 (7)	0.0234 (3)
N1	0.67586 (19)	0.66128 (12)	0.50171 (6)	0.0203 (3)
O1	0.68052 (16)	0.68272 (12)	0.56832 (5)	0.0253 (3)
O2	0.49243 (17)	0.65449 (12)	0.46095 (5)	0.0299 (3)
O3	0.86091 (16)	0.64795 (12)	0.47709 (5)	0.0275 (3)
H1A	0.1455	0.4851	0.6391	0.027*
H1B	0.0313	0.6232	0.6740	0.027*
H2A	0.3580	0.6659	0.5838	0.023*
H2B	0.1130	0.6598	0.5540	0.023*
H3A	0.2894	0.8733	0.6540	0.028*
H3B	0.0340	0.8711	0.6129	0.028*
H4A	0.4269	0.9196	0.5447	0.041*
H4B	0.2443	1.0443	0.5567	0.041*
H4C	0.1746	0.9104	0.5018	0.041*
H12	0.2259	0.7366	0.7820	0.027*
H13	0.5360	0.7459	0.8738	0.031*
H14	0.8607	0.6063	0.8647	0.033*
H15	0.8718	0.4519	0.7646	0.032*
H16	0.5659	0.4458	0.6718	0.028*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N2	0.0182 (5)	0.0226 (6)	0.0175 (6)	−0.0014 (4)	0.0028 (4)	0.0001 (4)
C1	0.0217 (7)	0.0252 (7)	0.0205 (7)	−0.0050 (5)	0.0024 (5)	0.0035 (5)
C3	0.0249 (7)	0.0215 (7)	0.0227 (7)	−0.0012 (5)	0.0038 (5)	−0.0017 (5)
C4	0.0294 (8)	0.0242 (7)	0.0284 (8)	−0.0002 (6)	0.0033 (6)	0.0040 (5)
C11	0.0206 (7)	0.0196 (6)	0.0186 (6)	−0.0024 (5)	0.0038 (5)	0.0033 (5)
C12	0.0261 (7)	0.0213 (7)	0.0210 (7)	0.0027 (5)	0.0065 (5)	0.0014 (5)
C13	0.0361 (8)	0.0228 (7)	0.0180 (7)	−0.0022 (6)	0.0030 (6)	−0.0004 (5)
C14	0.0269 (7)	0.0327 (8)	0.0210 (7)	−0.0030 (6)	−0.0009 (5)	0.0056 (6)
C15	0.0223 (7)	0.0340 (8)	0.0250 (7)	0.0058 (6)	0.0058 (6)	0.0057 (6)
C16	0.0274 (7)	0.0237 (7)	0.0201 (7)	0.0022 (5)	0.0071 (5)	0.0002 (5)
N1	0.0195 (6)	0.0205 (6)	0.0203 (6)	−0.0008 (4)	0.0012 (4)	0.0002 (4)
O1	0.0220 (5)	0.0372 (6)	0.0165 (5)	0.0004 (4)	0.0023 (4)	−0.0028 (4)
O2	0.0226 (5)	0.0397 (6)	0.0248 (5)	−0.0008 (4)	−0.0054 (4)	−0.0018 (4)
O3	0.0221 (5)	0.0384 (6)	0.0232 (5)	−0.0002 (4)	0.0068 (4)	−0.0024 (4)

Geometric parameters (Å, º) top

C1—N2	1.5013 (16)	C11—C12	1.3950 (18)
C1—C11	1.5068 (18)	C12—C13	1.390 (2)
C1—H1A	0.99	C12—H12	0.95
C1—H1B	0.99	C13—C14	1.382 (2)
N2—C3	1.4915 (17)	C13—H13	0.95
N2—H2A	0.92	C14—C15	1.392 (2)
N2—H2B	0.92	C14—H14	0.95
C3—C4	1.5152 (19)	C15—C16	1.385 (2)
C3—H3A	0.99	C15—H15	0.95
C3—H3B	0.99	C16—H16	0.95
C4—H4A	0.98	N1—O1	1.2601 (15)
C4—H4B	0.98	N1—O2	1.2404 (15)
C4—H4C	0.98	N1—O3	1.2603 (14)
C11—C16	1.3944 (19)

N2—C1—C11	111.88 (10)	H4B—C4—H4C	109.5
N2—C1—H1A	109.2	C16—C11—C12	118.92 (12)
C11—C1—H1A	109.2	C16—C11—C1	119.79 (12)
N2—C1—H1B	109.2	C12—C11—C1	121.29 (12)
C11—C1—H1B	109.2	C13—C12—C11	120.49 (13)
H1A—C1—H1B	107.9	C13—C12—H12	119.8
C3—N2—C1	113.50 (10)	C11—C12—H12	119.8
C3—N2—H2A	108.9	C14—C13—C12	120.13 (13)
C1—N2—H2A	108.9	C14—C13—H13	119.9
C3—N2—H2B	108.9	C12—C13—H13	119.9
C1—N2—H2B	108.9	C13—C14—C15	119.80 (13)
H2A—N2—H2B	107.7	C13—C14—H14	120.1
N2—C3—C4	110.90 (11)	C15—C14—H14	120.1
N2—C3—H3A	109.5	C16—C15—C14	120.18 (13)
C4—C3—H3A	109.5	C16—C15—H15	119.9
N2—C3—H3B	109.5	C14—C15—H15	119.9
C4—C3—H3B	109.5	C15—C16—C11	120.46 (13)
H3A—C3—H3B	108.0	C15—C16—H16	119.8
C3—C4—H4A	109.5	C11—C16—H16	119.8
C3—C4—H4B	109.5	O1—N1—O2	120.60 (11)
H4A—C4—H4B	109.5	O2—N1—O3	120.54 (11)
C3—C4—H4C	109.5	O1—N1—O3	118.85 (11)
H4A—C4—H4C	109.5

C12—C11—C1—N2	100.66 (14)	C11—C12—C13—C14	−0.8 (2)
C11—C1—N2—C3	−74.31 (14)	C12—C13—C14—C15	−0.9 (2)
C1—N2—C3—C4	173.25 (11)	C13—C14—C15—C16	1.6 (2)
N2—C1—C11—C16	−79.46 (15)	C14—C15—C16—C11	−0.6 (2)
C16—C11—C12—C13	1.7 (2)	C12—C11—C16—C15	−1.0 (2)
C1—C11—C12—C13	−178.38 (12)	C1—C11—C16—C15	179.08 (12)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	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−1/2, −y+3/2, z+1/2.

Experimental details

Crystal data
Chemical formula	C₉H₁₄N⁺·NO₃⁻
M_r	198.22
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	120
a, b, c (Å)	5.9538 (4), 8.9940 (6), 18.7484 (8)
β (°)	98.324 (4)
V (Å³)	993.37 (10)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.50 × 0.30 × 0.20

Data collection
Diffractometer	Nonius KappaCCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2003)
T_min, T_max	0.969, 0.980
No. of measured, independent and observed [I > 2σ(I)] reflections	13128, 2262, 1869
R_int	0.036
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.043, 0.132, 1.11
No. of reflections	2262
No. of parameters	128
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	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—O1	1.2601 (15)	N1—O3	1.2603 (14)
N1—O2	1.2404 (15)

O1—N1—O2	120.60 (11)	O1—N1—O3	118.85 (11)
O2—N1—O3	120.54 (11)

C12—C11—C1—N2	100.66 (14)	C1—N2—C3—C4	173.25 (11)
C11—C1—N2—C3	−74.31 (14)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	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−1/2, −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

Bernstein, 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
Ferguson, G. (1999). PRPKAPPA. University of Guelph, Canada. Google Scholar
Gregson, 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
Hooft, R. W. W. (1999). COLLECT. Nonius BV, Delft, The Netherlands. Google Scholar
McArdle, P. (2003). OSCAIL for Windows. Version 10. Crystallography Centre, Chemistry Department, NUI Galway, Ireland. Google Scholar
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. Google Scholar
Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2003). SADABS. Version 2.10. University of Göttingen, Germany. Google Scholar
Spek, A. L. (2003). J. Appl. Cryst. 36, 7–13. Web of Science CrossRef CAS IUCr Journals Google Scholar

© International Union of Crystallography. Prior permission is not required to reproduce short quotations, tables and figures from this article, provided the original authors and source are cited. For more information, click here.

STRUCTURAL
CHEMISTRY

ISSN: 2053-2296

Volume 61| Part 11| November 2005| Pages o645-o647

doi:10.1107/S0108270105031719

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text
		Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text
		Text

Search term		doi		Advanced search
Author		volume	page

organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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

Comment

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

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