N-[2-(2-Chloro-phen-yl)-2-hydroxy-ethyl]propan-2-aminium chloride.

In the title compound, C(11)H(17)ClNO(+)·Cl(-), the side chain of the ethyl-amine group is orientated approximately perpendicular to the benzene ring, the dihedral angle between the C/C/N plane of the ethyl-amine group and the benzene plane being 83.5 (3)°. In the crystal structure, inter-molecular O-H⋯Cl and N-H⋯Cl hydrogen bonds are observed. The crystal studied was an inversion twin with a 0.51 (10):0.49 (10) domain ratio.

Related literature

For a related structure, see: Tang et al. (2009 ▶).

Experimental

Crystal data

C11H17ClNO+·Cl−

M = 250.16

Orthorhombic,

a = 7.3460 (3) Å

b = 11.7721 (5) Å

c = 15.2377 (8) Å

V = 1317.72 (10) Å3

Z = 4

Mo Kα radiation

μ = 0.47 mm−1

T = 296 K

0.40 × 0.36 × 0.32 mm

Data collection

Rigaku R-AXIS RAPID diffractometer

Absorption correction: multi-scan (; Higashi, 1995 ▶) T min = 0.835, T max = 0.864

12577 measured reflections

2977 independent reflections

1874 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.032

wR(F 2) = 0.107

S = 1.00

2977 reflections

140 parameters

H-atom parameters constrained

Δρmax = 0.29 e Å−3

Δρmin = −0.29 e Å−3

Absolute structure: Flack (1983 ▶), 1243 Friedel pairs

Flack parameter: 0.51 (10)

Data collection: PROCESS-AUTO (Rigaku, 2006 ▶); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2007 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809031146/is2447sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809031146/is2447Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C11H17ClNO+·Cl−	F(000) = 528
Mr = 250.16	Dx = 1.261 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 8627 reflections
a = 7.3460 (3) Å	θ = 3.1–27.4°
b = 11.7721 (5) Å	µ = 0.47 mm−1
c = 15.2377 (8) Å	T = 296 K
V = 1317.72 (10) Å3	Chunk, colorless
Z = 4	0.40 × 0.36 × 0.32 mm

Rigaku R-AXIS RAPID diffractometer	2977 independent reflections
Radiation source: rotating anode	1874 reflections with I > 2σ(I)
graphite	Rint = 0.031
Detector resolution: 10.00 pixels mm-1	θmax = 27.4°, θmin = 3.1°
ω scans	h = −9→9
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	k = −15→14
Tmin = 0.835, Tmax = 0.864	l = −19→19
12577 measured reflections

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.032	w = 1/[σ2(Fo2) + (0.0431P)2 + 0.5P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.107	(Δ/σ)max < 0.001
S = 1.00	Δρmax = 0.29 e Å−3
2977 reflections	Δρmin = −0.29 e Å−3
140 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 restraints	Extinction coefficient: 0.0054 (12)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 1243 Friedel pairs
Secondary atom site location: difference Fourier map	Flack parameter: 0.51 (10)

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.

	x	y	z	Uiso*/Ueq
Cl2	0.51205 (10)	0.14865 (6)	0.44638 (6)	0.0648 (2)
Cl1	0.44580 (11)	0.75320 (8)	0.58138 (6)	0.0779 (3)
O1	0.3177 (3)	0.44304 (18)	0.42787 (16)	0.0698 (6)
H1	0.2294	0.4174	0.4542	0.105*
N1	0.5869 (3)	0.37691 (19)	0.55437 (15)	0.0522 (6)
H111	0.7029	0.3550	0.5628	0.063*
H112	0.5341	0.3244	0.5198	0.063*
C7	0.4020 (4)	0.5277 (2)	0.4795 (2)	0.0489 (7)
H7	0.3296	0.5422	0.5323	0.059*
C6	0.4249 (3)	0.6368 (2)	0.42750 (19)	0.0488 (6)
C1	0.4496 (3)	0.7418 (2)	0.4678 (2)	0.0546 (7)
C8	0.5901 (4)	0.4868 (2)	0.5047 (2)	0.0537 (7)
H8A	0.6623	0.4771	0.4519	0.064*
H8B	0.6487	0.5443	0.5405	0.064*
C9	0.4922 (4)	0.3739 (2)	0.64202 (18)	0.0579 (7)
H9	0.3639	0.3936	0.6332	0.069*
C5	0.4305 (4)	0.6352 (3)	0.3365 (2)	0.0680 (9)
H5	0.4144	0.5669	0.3069	0.082*
C11	0.5028 (6)	0.2537 (3)	0.6769 (2)	0.0777 (9)
H11A	0.6279	0.2330	0.6854	0.093*
H11B	0.4477	0.2027	0.6355	0.093*
H11C	0.4393	0.2492	0.7319	0.093*
C2	0.4764 (4)	0.8401 (3)	0.4204 (3)	0.0729 (10)
H2	0.4904	0.9091	0.4494	0.088*
C3	0.4824 (5)	0.8360 (4)	0.3318 (3)	0.0920 (13)
H3	0.5018	0.9022	0.2998	0.110*
C4	0.4597 (5)	0.7344 (5)	0.2889 (3)	0.0897 (12)
H4	0.4639	0.7319	0.2279	0.108*
C10	0.5746 (6)	0.4584 (3)	0.7044 (2)	0.0928 (13)
H10A	0.5099	0.4564	0.7591	0.111*
H10B	0.5665	0.5332	0.6797	0.111*
H10C	0.7001	0.4396	0.7144	0.111*

	U11	U22	U33	U12	U13	U23
Cl2	0.0489 (4)	0.0509 (3)	0.0944 (6)	0.0007 (3)	0.0009 (4)	−0.0054 (4)
Cl1	0.0692 (5)	0.0819 (6)	0.0825 (6)	−0.0038 (5)	−0.0021 (4)	−0.0313 (5)
O1	0.0628 (13)	0.0559 (12)	0.0909 (18)	−0.0136 (10)	−0.0123 (12)	−0.0113 (12)
N1	0.0435 (11)	0.0498 (13)	0.0633 (15)	−0.0017 (10)	−0.0009 (11)	0.0057 (11)
C7	0.0399 (13)	0.0455 (14)	0.0613 (17)	−0.0049 (12)	−0.0016 (12)	−0.0044 (13)
C6	0.0393 (12)	0.0465 (14)	0.0606 (18)	0.0017 (12)	−0.0015 (12)	0.0003 (13)
C1	0.0364 (13)	0.0510 (15)	0.0765 (19)	0.0010 (13)	0.0021 (13)	−0.0009 (15)
C8	0.0438 (14)	0.0483 (15)	0.069 (2)	−0.0023 (13)	0.0006 (13)	0.0073 (13)
C9	0.0513 (15)	0.0647 (18)	0.0577 (17)	−0.0011 (16)	0.0030 (15)	0.0076 (13)
C5	0.0671 (19)	0.080 (2)	0.057 (2)	0.0136 (19)	0.0015 (15)	0.0010 (17)
C11	0.087 (2)	0.074 (2)	0.071 (2)	−0.006 (3)	0.003 (2)	0.0193 (17)
C2	0.0455 (15)	0.0489 (16)	0.124 (3)	−0.0015 (15)	0.007 (2)	0.0108 (18)
C3	0.059 (2)	0.082 (3)	0.135 (4)	0.012 (2)	0.010 (2)	0.050 (3)
C4	0.076 (3)	0.125 (3)	0.068 (2)	0.020 (3)	0.0058 (19)	0.039 (2)
C10	0.123 (3)	0.086 (3)	0.069 (2)	−0.011 (3)	−0.002 (2)	−0.012 (2)

Cl1—C1	1.736 (3)	C9—C11	1.514 (4)
O1—C7	1.413 (3)	C9—H9	0.9800
O1—H1	0.8200	C5—C4	1.391 (5)
N1—C8	1.499 (3)	C5—H5	0.9300
N1—C9	1.506 (3)	C11—H11A	0.9600
N1—H111	0.9000	C11—H11B	0.9600
N1—H112	0.9000	C11—H11C	0.9600
C7—C8	1.513 (4)	C2—C3	1.352 (6)
C7—C6	1.518 (4)	C2—H2	0.9300
C7—H7	0.9800	C3—C4	1.373 (7)
C6—C5	1.387 (4)	C3—H3	0.9300
C6—C1	1.393 (4)	C4—H4	0.9300
C1—C2	1.378 (5)	C10—H10A	0.9600
C8—H8A	0.9700	C10—H10B	0.9600
C8—H8B	0.9700	C10—H10C	0.9600
C9—C10	1.503 (5)
C7—O1—H1	109.5	C10—C9—H9	108.5
C8—N1—C9	118.4 (2)	N1—C9—H9	108.5
C8—N1—H111	107.7	C11—C9—H9	108.5
C9—N1—H111	107.7	C6—C5—C4	121.0 (4)
C8—N1—H112	107.7	C6—C5—H5	119.5
C9—N1—H112	107.7	C4—C5—H5	119.5
H111—N1—H112	107.1	C9—C11—H11A	109.5
O1—C7—C8	108.5 (2)	C9—C11—H11B	109.5
O1—C7—C6	110.8 (2)	H11A—C11—H11B	109.5
C8—C7—C6	107.5 (2)	C9—C11—H11C	109.5
O1—C7—H7	110.0	H11A—C11—H11C	109.5
C8—C7—H7	110.0	H11B—C11—H11C	109.5
C6—C7—H7	110.0	C3—C2—C1	119.9 (3)
C5—C6—C1	116.7 (3)	C3—C2—H2	120.1
C5—C6—C7	120.9 (3)	C1—C2—H2	120.1
C1—C6—C7	122.4 (2)	C2—C3—C4	120.2 (3)
C2—C1—C6	122.2 (3)	C2—C3—H3	119.9
C2—C1—Cl1	117.4 (3)	C4—C3—H3	119.9
C6—C1—Cl1	120.4 (2)	C3—C4—C5	120.1 (4)
N1—C8—C7	112.9 (2)	C3—C4—H4	120.0
N1—C8—H8A	109.0	C5—C4—H4	120.0
C7—C8—H8A	109.0	C9—C10—H10A	109.5
N1—C8—H8B	109.0	C9—C10—H10B	109.5
C7—C8—H8B	109.0	H10A—C10—H10B	109.5
H8A—C8—H8B	107.8	C9—C10—H10C	109.5
C10—C9—N1	111.1 (3)	H10A—C10—H10C	109.5
C10—C9—C11	112.1 (3)	H10B—C10—H10C	109.5
N1—C9—C11	108.0 (2)
O1—C7—C6—C5	−23.6 (4)	C6—C7—C8—N1	−178.2 (2)
C8—C7—C6—C5	94.8 (3)	C8—N1—C9—C10	−58.5 (3)
O1—C7—C6—C1	159.4 (2)	C8—N1—C9—C11	178.2 (3)
C8—C7—C6—C1	−82.2 (3)	C1—C6—C5—C4	0.1 (4)
C5—C6—C1—C2	0.6 (4)	C7—C6—C5—C4	−177.1 (3)
C7—C6—C1—C2	177.8 (2)	C6—C1—C2—C3	−1.1 (4)
C5—C6—C1—Cl1	−179.8 (2)	Cl1—C1—C2—C3	179.4 (3)
C7—C6—C1—Cl1	−2.7 (3)	C1—C2—C3—C4	0.7 (5)
C9—N1—C8—C7	−62.6 (3)	C2—C3—C4—C5	0.0 (6)
O1—C7—C8—N1	−58.4 (3)	C6—C5—C4—C3	−0.5 (5)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H112···Cl2	0.90	2.36	3.199 (2)	156
O1—H1···Cl2i	0.82	2.33	3.143 (2)	169
N1—H111···Cl2ii	0.90	2.28	3.138 (2)	160

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H112⋯Cl2	0.90	2.36	3.199 (2)	156
O1—H1⋯Cl2i	0.82	2.33	3.143 (2)	169
N1—H111⋯Cl2ii	0.90	2.28	3.138 (2)	160

Symmetry codes: (i) ; (ii) .