(tert-But­yl)(2-hy­droxy­eth­yl)ammonium chloride

Valerio-Cárdenas, C.; Hernández-Ortega, S.; Morales-Morales, D.

doi:10.1107/S1600536814012847

organic compounds

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ISSN: 2056-9890

Volume 70| Part 7| July 2014| Page o783

https://doi.org/10.1107/S1600536814012847

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(tert-Butyl)(2-hydroxyethyl)ammonium chloride

Cintya Valerio-Cárdenas,^a ^* Simón Hernández-Ortega ^a and David Morales-Morales ^a

^aInstituto de Química, Universidad Nacional Autónoma de México, Circuito Exterior, Ciudad Universitaria, Coyoacán, México, DF 04510, Mexico
^*Correspondence e-mail: cintyavc@hotmail.com

(Received 18 February 2014; accepted 2 June 2014; online 18 June 2014)

In the cation of the title molecular salt, C₆H₁₆NO⁺·Cl⁻, the N—C—C—O torsion angle is 176.5 (2)°. In the crystal, the cations and chloride ions are linked by N—H⋯O and O—H⋯O hydrogen bonds, generating a two-dimensional network parallel to (100).

CCDC reference: 1006385

Related literature

For the chiral pool synthesis of naturally occurring molecules, see: Coppola & Schuster (1987 ); Bergmeier & Stanchina (1999 ). For pharmacologic synthesis, see: Gante (1994 ); Tok & Rando (1998 ).

Experimental

Crystal data

C₆H₁₆NO⁺·Cl⁻
M_r = 153.65
Monoclinic, P 2₁ /c
a = 8.5204 (3) Å
b = 7.8742 (3) Å
c = 14.1844 (5) Å
β = 105.804 (1)°
V = 915.68 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.35 mm⁻¹
T = 298 K
0.40 × 0.10 × 0.03 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
5487 measured reflections
1668 independent reflections
1071 reflections with I > 2σ(I)
R_int = 0.058

Refinement

R[F² > 2σ(F²)] = 0.046
wR(F²) = 0.124
S = 1.00
1668 reflections
94 parameters
3 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.48 e Å⁻³
Δρ_min = −0.25 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯Cl1ⁱ	0.86 (1)	2.29 (1)	3.140 (2)	167 (3)
N3—H3A⋯Cl1	0.90 (1)	2.27 (1)	3.144 (2)	166 (2)
N3—H3B⋯Cl1ⁱⁱ	0.89 (1)	2.30 (1)	3.190 (2)	175 (2)
Symmetry codes: (i) $[x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ ; (ii) $[-x+1, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Data collection: APEX2 (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information

CCDC reference: 1006385

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S1600536814012847/gw2144sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536814012847/gw2144Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536814012847/gw2144Isup3.cml

checkCIF report

Comment top

Amino alcohols are some of the most versatile starting materials both at the laboratory and at the industrial scale and have been widely used for a large number of applications. Among which stands the chiral pool synthesis of naturally occurring molecules (Coppola et al. 1987; Bergmeier et al. 1999). These compounds have also displayed important biological activities and are of interest for the development of synthetic methods in the pharmaceutical industry (Gante, 1994; Tok et al. 1998). Based on the above, we report here the crystal structure of N-((2-hydroxyethyl)tertbutyl)ammonium chloride and discuss its geometry and intermolecular interactions.

The molecular structure of the title compound [(HOC₂H₄)((CH₃)₃C)NH₂]Cl^- (Fig. 1), consists of an ionic species, exhibiting the nitrogen atom in a tetrahedral geometry. The dihedral angle between the tertbutyl and the 2-hydroxyethyl moieties is almost plane (173.34 (2)°) as a result of the reduced steric effects. In the asymmetric unit the Cl atom is linked by a N3—H3A···Cl1 interaction (2.266 (11) Å). In the crystal the Cl atom is acting as tri-acceptor H-bonding, such that, the anion and cation species are linked through O1—H1···Cl1 with distances of 2.294 (13) Å, leading to stairs aligned along the ac plane (symmetry code x, -y + 3/2, z + 1/2). These stairs are expanded by a third intermolecular interaction N3—H3B···Cl1 (2.304 (10) Å) along the b axis with symmetry code -x + 1,y - 1/2,-z + 3/2 (see Table 1, Fig. 2).

Related literature top

For naturally occurring molecules, see: Coppola & Schuster (1987); Bergmeier & Stanchina (1999). For pharmacologic synthesis, see: Gante (1994); Tok & Rando (1998). For chiral auxiliaries, see: Ager et al. (1996); Studer (1996).

Experimental top

The title compound was isolated from the reaction of [S₂CN(^tBu)(EtOH)] and [NiCl₂(PPh₃)₂] in a 1:1 molar ratio in ethanol. Colourless crystals suitable for single-crystal X-ray diffraction analysis were obtained from a solvent system ether/CH₂Cl₂.

Structure description top

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound showing the atom labelling and displacement ellipsoids at the 40% of probability.
	Fig. 2. A view in projection on the direction of the chain. The O—H···Cl and N—H···Cl interactions are shown as dashed lines.

(tert-Butyl)(2-hydroxyethyl)ammonium chloride top

Crystal data top

C₆H₁₆NO⁺·Cl⁻	F(000) = 336
M_r = 153.65	D_x = 1.115 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2475 reflections
a = 8.5204 (3) Å	θ = 2.5–25.3°
b = 7.8742 (3) Å	µ = 0.35 mm⁻¹
c = 14.1844 (5) Å	T = 298 K
β = 105.804 (1)°	Prism, colourless
V = 915.68 (6) Å³	0.40 × 0.10 × 0.03 mm
Z = 4

Data collection top

Bruker APEXII CCD area-detector diffractometer	R_int = 0.058
Detector resolution: 0.83 pixels mm^-1	θ_max = 25.3°, θ_min = 2.5°
ω scans	h = −5→10
5487 measured reflections	k = −8→9
1668 independent reflections	l = −17→16
1071 reflections with I > 2σ(I)

Refinement top

Refinement on F²	3 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.046	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.124	w = 1/[σ²(F_o²) + (0.0584P)²] where P = (F_o² + 2F_c²)/3
S = 1.00	(Δ/σ)_max = 0.001
1668 reflections	Δρ_max = 0.48 e Å⁻³
94 parameters	Δρ_min = −0.25 e Å⁻³

Crystal data top

C₆H₁₆NO⁺·Cl⁻	V = 915.68 (6) Å³
M_r = 153.65	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 8.5204 (3) Å	µ = 0.35 mm⁻¹
b = 7.8742 (3) Å	T = 298 K
c = 14.1844 (5) Å	0.40 × 0.10 × 0.03 mm
β = 105.804 (1)°

Data collection top

Bruker APEXII CCD area-detector diffractometer	1071 reflections with I > 2σ(I)
5487 measured reflections	R_int = 0.058
1668 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	3 restraints
wR(F²) = 0.124	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	Δρ_max = 0.48 e Å⁻³
1668 reflections	Δρ_min = −0.25 e Å⁻³
94 parameters

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.

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

	x	y	z	U_iso*/U_eq
Cl1	0.44289 (9)	0.82425 (9)	0.62991 (4)	0.0579 (3)
O1	0.2643 (2)	0.8483 (3)	0.92991 (15)	0.0690 (6)
H1	0.303 (4)	0.811 (4)	0.9889 (11)	0.083*
C1	0.3512 (3)	0.7606 (4)	0.87548 (19)	0.0531 (7)
H1A	0.3003	0.7781	0.8062	0.064*
H1B	0.3488	0.6400	0.8889	0.064*
C2	0.5253 (3)	0.8207 (3)	0.90041 (18)	0.0436 (6)
H2A	0.5280	0.9397	0.8832	0.052*
H2B	0.5742	0.8098	0.9704	0.052*
N3	0.6212 (2)	0.7191 (3)	0.84643 (15)	0.0383 (5)
H3A	0.579 (3)	0.734 (3)	0.7818 (8)	0.046*
H3B	0.607 (3)	0.6079 (13)	0.8511 (17)	0.046*
C4	0.8038 (3)	0.7496 (3)	0.87151 (19)	0.0454 (7)
C5	0.8775 (3)	0.7126 (4)	0.9796 (2)	0.0686 (9)
H5A	0.8423	0.6028	0.9950	0.082*
H5B	0.8427	0.7976	1.0181	0.082*
H5C	0.9944	0.7142	0.9941	0.082*
C6	0.8687 (3)	0.6245 (4)	0.8087 (2)	0.0728 (9)
H6A	0.8452	0.5105	0.8247	0.087*
H6B	0.9845	0.6386	0.8214	0.087*
H6C	0.8172	0.6459	0.7407	0.087*
C7	0.8344 (3)	0.9303 (4)	0.8456 (2)	0.0678 (9)
H7A	0.9497	0.9489	0.8584	0.081*
H7B	0.7906	1.0071	0.8844	0.081*
H7C	0.7825	0.9498	0.7774	0.081*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0865 (6)	0.0441 (4)	0.0413 (4)	0.0031 (3)	0.0142 (4)	−0.0011 (3)
O1	0.0533 (13)	0.0912 (16)	0.0646 (13)	0.0179 (11)	0.0194 (11)	0.0001 (13)
C1	0.0387 (17)	0.0772 (19)	0.0429 (15)	0.0068 (14)	0.0103 (12)	−0.0066 (15)
C2	0.0407 (16)	0.0462 (15)	0.0467 (14)	0.0013 (11)	0.0166 (12)	−0.0050 (13)
N3	0.0377 (13)	0.0364 (11)	0.0406 (11)	0.0007 (9)	0.0101 (10)	−0.0003 (11)
C4	0.0342 (15)	0.0438 (14)	0.0584 (17)	0.0013 (11)	0.0130 (13)	−0.0028 (14)
C5	0.0472 (19)	0.084 (2)	0.0657 (19)	0.0039 (15)	−0.0004 (15)	0.0017 (18)
C6	0.0513 (19)	0.079 (2)	0.095 (2)	0.0051 (16)	0.0311 (17)	−0.020 (2)
C7	0.0463 (18)	0.0607 (19)	0.099 (2)	−0.0077 (14)	0.0232 (17)	0.0038 (19)

Geometric parameters (Å, º) top

O1—C1	1.390 (3)	C4—C5	1.519 (4)
O1—H1	0.862 (10)	C4—C6	1.529 (4)
C1—C2	1.504 (4)	C5—H5A	0.9600
C1—H1A	0.9700	C5—H5B	0.9600
C1—H1B	0.9700	C5—H5C	0.9600
C2—N3	1.495 (3)	C6—H6A	0.9600
C2—H2A	0.9700	C6—H6B	0.9600
C2—H2B	0.9700	C6—H6C	0.9600
N3—C4	1.518 (3)	C7—H7A	0.9600
N3—H3A	0.896 (9)	C7—H7B	0.9600
N3—H3B	0.888 (10)	C7—H7C	0.9600
C4—C7	1.510 (4)

C1—O1—H1	104 (2)	C7—C4—C6	110.5 (2)
O1—C1—C2	110.7 (2)	N3—C4—C6	105.8 (2)
O1—C1—H1A	109.5	C5—C4—C6	110.4 (2)
C2—C1—H1A	109.5	C4—C5—H5A	109.5
O1—C1—H1B	109.5	C4—C5—H5B	109.5
C2—C1—H1B	109.5	H5A—C5—H5B	109.5
H1A—C1—H1B	108.1	C4—C5—H5C	109.5
N3—C2—C1	110.6 (2)	H5A—C5—H5C	109.5
N3—C2—H2A	109.5	H5B—C5—H5C	109.5
C1—C2—H2A	109.5	C4—C6—H6A	109.5
N3—C2—H2B	109.5	C4—C6—H6B	109.5
C1—C2—H2B	109.5	H6A—C6—H6B	109.5
H2A—C2—H2B	108.1	C4—C6—H6C	109.5
C2—N3—C4	117.61 (19)	H6A—C6—H6C	109.5
C2—N3—H3A	109.4 (16)	H6B—C6—H6C	109.5
C4—N3—H3A	108.7 (16)	C4—C7—H7A	109.5
C2—N3—H3B	112.9 (15)	C4—C7—H7B	109.5
C4—N3—H3B	106.6 (15)	H7A—C7—H7B	109.5
H3A—N3—H3B	100 (2)	C4—C7—H7C	109.5
C7—C4—N3	109.1 (2)	H7A—C7—H7C	109.5
C7—C4—C5	112.0 (2)	H7B—C7—H7C	109.5
N3—C4—C5	108.8 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···Cl1ⁱ	0.86 (1)	2.29 (1)	3.140 (2)	167 (3)
N3—H3A···Cl1	0.90 (1)	2.27 (1)	3.144 (2)	166 (2)
N3—H3B···Cl1ⁱⁱ	0.89 (1)	2.30 (1)	3.190 (2)	175 (2)

Symmetry codes: (i) x, −y+3/2, z+1/2; (ii) −x+1, y−1/2, −z+3/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···Cl1ⁱ	0.862 (10)	2.294 (13)	3.140 (2)	167 (3)
N3—H3A···Cl1	0.896 (9)	2.266 (11)	3.144 (2)	166 (2)
N3—H3B···Cl1ⁱⁱ	0.888 (10)	2.304 (10)	3.190 (2)	175 (2)

Symmetry codes: (i) x, −y+3/2, z+1/2; (ii) −x+1, y−1/2, −z+3/2.

Acknowledgements

CVC would like to thank CONACYT for a postdoctoral scholarship (290805–UNAM). Support of this research by CONACYT (CB2010–154732) and PAPIIT (IN201711–3 and IN213214–3) is gratefully acknowledged.

References

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