(tert-But-yl)(2-hy-droxy-eth-yl)ammonium chloride.

In the cation of the title mol-ecular 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).

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 = 153.65

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.124

S = 1.00

1668 reflections

94 parameters

3 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.48 e Å−3

Δρmin = −0.25 e Å−3

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.

Crystal structure: contains datablock(s) I. DOI: 10.1107/S1600536814012847/gw2144sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814012847/gw2144Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814012847/gw2144Isup3.cml

CCDC reference: 1006385

Additional supporting information: crystallographic information; 3D view; checkCIF report

C6H16NO+·Cl−	F(000) = 336
Mr = 153.65	Dx = 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

Bruker APEXII CCD area-detector diffractometer	Rint = 0.058
Detector resolution: 0.83 pixels mm-1	θmax = 25.3°, θmin = 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 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(Fo2) + (0.0584P)2] where P = (Fo2 + 2Fc2)/3
S = 1.00	(Δ/σ)max = 0.001
1668 reflections	Δρmax = 0.48 e Å−3
94 parameters	Δρmin = −0.25 e Å−3

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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)

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) ; (ii) .