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

The asymmetric unit of the title compound, C(11)H(17)ClNO(+)·0.5C(2)O(4) (2-), consists of one N-[2-(2-chloro-phen-yl)-2-hydroxy-ethyl]propan-2-ammonium cation and one-half of a centrosymmetric oxalate anion. In the cation, the C/C/N plane of the ethyl-ammonium group is almost perpendicular to the benzene ring, with a dihedral angle of 88.72 (17)°. In the crystal structure, the two components are connected by O-H⋯O and N-H⋯O hydrogen bonds, forming a supra-molecular tape along the a axis. Between the tapes, a C-H⋯O inter-action is observed.

Related literature

For related structures, see: Czugler et al. (2007 ▶); Marsau et al. (1979 ▶); Martin & Pinkerton (1998 ▶); Tang et al. (2009 ▶).

Experimental

Crystal data

C11H17ClNO+·0.5C2O4 2−

M = 258.72

Monoclinic,

a = 6.9951 (3) Å

b = 17.8821 (8) Å

c = 11.2236 (6) Å

β = 110.8377 (13)°

V = 1312.10 (11) Å3

Z = 4

Mo Kα radiation

μ = 0.29 mm−1

T = 296 K

0.53 × 0.24 × 0.22 mm

Data collection

Rigaku R-AXIS RAPID diffractometer

Absorption correction: multi-scan (; Higashi, 1995 ▶) T min = 0.836, T max = 0.939

12562 measured reflections

2978 independent reflections

1974 reflections with F 2 > 2σ(F 2)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.089

S = 1.00

2978 reflections

156 parameters

H-atom parameters constrained

Δρmax = 0.26 e Å−3

Δρmin = −0.28 e Å−3

Data collection: PROCESS-AUTO (Rigaku/MSC, 2004 ▶); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004 ▶); program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: CrystalStructure (Rigaku/MSC, 2004 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809022740/is2425sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809022740/is2425Isup2.hkl

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

C11H17ClNO+·0.5C2O42−	F(000) = 548.00
Mr = 258.72	Dx = 1.310 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71075 Å
Hall symbol: -P 2yn	Cell parameters from 8056 reflections
a = 6.9951 (3) Å	θ = 3.0–27.4°
b = 17.8821 (8) Å	µ = 0.29 mm−1
c = 11.2236 (6) Å	T = 296 K
β = 110.8377 (13)°	Chunk, colorless
V = 1312.10 (11) Å3	0.53 × 0.24 × 0.22 mm
Z = 4

Rigaku R-AXIS RAPID diffractometer	1974 reflections with F2 > 2σ(F2)
Detector resolution: 10.00 pixels mm-1	Rint = 0.032
ω scans	θmax = 27.4°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −8→9
Tmin = 0.836, Tmax = 0.939	k = −23→23
12562 measured reflections	l = −14→14
2978 independent reflections

Refinement on F2	w = 1/[σ2(Fo2) + (0.01P)2 + P] where P = (Fo2 + 2Fc2)/3
R[F2 > 2σ(F2)] = 0.036	(Δ/σ)max < 0.001
wR(F2) = 0.089	Δρmax = 0.26 e Å−3
S = 1.00	Δρmin = −0.28 e Å−3
2978 reflections	Extinction correction: SHELXL97 (Sheldrick, 2008)
156 parameters	Extinction coefficient: 0.0233 (11)
H-atom parameters constrained

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 using reflections with F2 > 2.0 σ(F2). The weighted R-factor(wR), goodness of fit (S) and R-factor (gt) are based on F, with F set to zero for negative F. The threshold expression of F2 > 2.0 σ(F2) is used only for calculating R-factor (gt).

	x	y	z	Uiso*/Ueq
Cl1	0.23746 (9)	0.45230 (3)	0.93857 (6)	0.0615 (2)
O1	−0.11289 (19)	0.65111 (8)	0.75048 (13)	0.0482 (3)
O2	0.7592 (2)	0.51348 (8)	0.52819 (14)	0.0533 (4)
O3	0.5489 (2)	0.57840 (8)	0.59837 (14)	0.0545 (4)
N1	0.1107 (2)	0.60395 (9)	0.59068 (14)	0.0407 (3)
C1	0.0439 (2)	0.59654 (11)	0.79473 (18)	0.0388 (4)
C2	0.1458 (2)	0.60032 (11)	0.93762 (18)	0.0396 (4)
C3	0.2344 (2)	0.53840 (12)	1.0113 (2)	0.0444 (4)
C4	0.3216 (3)	0.54182 (14)	1.1422 (2)	0.0586 (6)
C5	0.3270 (3)	0.60876 (17)	1.2028 (2)	0.0660 (6)
C6	0.2451 (3)	0.67209 (14)	1.1332 (2)	0.0625 (6)
C7	0.1541 (3)	0.66749 (12)	1.0015 (2)	0.0508 (5)
C8	0.2025 (2)	0.60998 (12)	0.73238 (19)	0.0449 (4)
C9	0.0455 (3)	0.67572 (12)	0.5169 (2)	0.0551 (5)
C10	0.2283 (4)	0.72303 (14)	0.5249 (2)	0.0847 (8)
C11	−0.0786 (4)	0.65560 (18)	0.3802 (2)	0.0861 (9)
C12	0.5890 (2)	0.52673 (10)	0.53649 (18)	0.0392 (4)
H1	−0.0160	0.5468	0.7708	0.047*
H4	0.3763	0.4991	1.1890	0.070*
H5	0.3860	0.6115	1.2912	0.079*
H6	0.2509	0.7177	1.1743	0.075*
H7	0.0975	0.7102	0.9551	0.061*
H9	−0.0414	0.7039	0.5528	0.066*
H81	0.3105	0.5731	0.7640	0.054*
H82	0.2596	0.6597	0.7548	0.054*
H101	0.3196	0.6945	0.4959	0.102*
H102	0.2982	0.7382	0.6116	0.102*
H103	0.1835	0.7665	0.4721	0.102*
H111	0.0052	0.6279	0.3442	0.103*
H112	−0.1938	0.6257	0.3779	0.103*
H113	−0.1261	0.7005	0.3318	0.103*
H201	−0.2198	0.6315	0.7042	0.056*
H301	0.0045	0.5758	0.5726	0.049*
H302	0.1996	0.5829	0.5649	0.049*

	U11	U22	U33	U12	U13	U23
Cl1	0.0558 (3)	0.0521 (3)	0.0871 (4)	0.0098 (2)	0.0383 (3)	0.0072 (2)
O1	0.0378 (7)	0.0493 (8)	0.0556 (9)	0.0046 (6)	0.0144 (6)	−0.0037 (6)
O2	0.0357 (7)	0.0627 (9)	0.0671 (10)	−0.0080 (6)	0.0252 (6)	−0.0189 (7)
O3	0.0411 (7)	0.0567 (8)	0.0662 (10)	0.0009 (6)	0.0198 (7)	−0.0194 (7)
N1	0.0394 (8)	0.0443 (8)	0.0430 (9)	0.0000 (7)	0.0206 (7)	−0.0041 (7)
C1	0.0341 (9)	0.0391 (9)	0.0451 (11)	−0.0016 (8)	0.0164 (8)	−0.0018 (8)
C2	0.0328 (9)	0.0469 (10)	0.0428 (11)	−0.0061 (8)	0.0182 (8)	−0.0007 (8)
C3	0.0328 (9)	0.0549 (12)	0.0512 (12)	0.0008 (8)	0.0221 (8)	0.0040 (9)
C4	0.0411 (11)	0.0856 (17)	0.0540 (14)	0.0099 (11)	0.0230 (10)	0.0188 (12)
C5	0.0499 (12)	0.101 (2)	0.0460 (13)	−0.0074 (13)	0.0160 (10)	0.0018 (14)
C6	0.0678 (14)	0.0711 (16)	0.0518 (14)	−0.0222 (13)	0.0254 (11)	−0.0182 (12)
C7	0.0561 (12)	0.0492 (11)	0.0501 (13)	−0.0104 (10)	0.0225 (10)	−0.0045 (9)
C8	0.0356 (9)	0.0569 (12)	0.0440 (11)	−0.0018 (9)	0.0163 (8)	−0.0020 (9)
C9	0.0627 (13)	0.0510 (12)	0.0593 (14)	0.0133 (10)	0.0313 (11)	0.0094 (10)
C10	0.111 (2)	0.0592 (15)	0.087 (2)	−0.0184 (15)	0.0387 (18)	0.0117 (14)
C11	0.0840 (19)	0.106 (2)	0.0580 (17)	−0.0009 (17)	0.0130 (14)	0.0242 (15)
C12	0.0346 (9)	0.0427 (10)	0.0420 (10)	0.0026 (8)	0.0158 (8)	0.0021 (8)

Cl1—C3	1.746 (2)	O1—H201	0.822
O1—C1	1.419 (2)	N1—H301	0.860
O2—C12	1.249 (2)	N1—H302	0.860
O3—C12	1.246 (2)	C1—H1	0.980
N1—C8	1.492 (2)	C4—H4	0.930
N1—C9	1.507 (2)	C5—H5	0.930
C1—C2	1.507 (2)	C6—H6	0.930
C1—C8	1.527 (3)	C7—H7	0.930
C2—C3	1.389 (2)	C8—H81	0.970
C2—C7	1.389 (2)	C8—H82	0.970
C3—C4	1.377 (3)	C9—H9	0.980
C4—C5	1.371 (3)	C10—H101	0.960
C5—C6	1.379 (3)	C10—H102	0.960
C6—C7	1.388 (3)	C10—H103	0.960
C9—C10	1.509 (4)	C11—H111	0.960
C9—C11	1.513 (3)	C11—H112	0.960
C12—C12i	1.552 (2)	C11—H113	0.960
C8—N1—C9	117.09 (15)	C8—C1—H1	109.1
O1—C1—C2	110.83 (16)	C3—C4—H4	120.3
O1—C1—C8	109.18 (16)	C5—C4—H4	120.3
C2—C1—C8	109.57 (14)	C4—C5—H5	119.9
C1—C2—C3	122.66 (18)	C6—C5—H5	119.9
C1—C2—C7	120.33 (17)	C5—C6—H6	120.2
C3—C2—C7	117.01 (17)	C7—C6—H6	120.2
Cl1—C3—C2	120.12 (15)	C2—C7—H7	119.3
Cl1—C3—C4	117.61 (17)	C6—C7—H7	119.3
C2—C3—C4	122.3 (2)	N1—C8—H81	108.9
C3—C4—C5	119.5 (2)	N1—C8—H82	108.9
C4—C5—C6	120.2 (2)	C1—C8—H81	108.9
C5—C6—C7	119.7 (2)	C1—C8—H82	108.9
C2—C7—C6	121.31 (19)	H81—C8—H82	109.5
N1—C8—C1	111.70 (14)	N1—C9—H9	108.9
N1—C9—C10	111.11 (17)	C10—C9—H9	108.9
N1—C9—C11	107.88 (18)	C11—C9—H9	108.9
C10—C9—C11	111.2 (2)	C9—C10—H101	109.5
O2—C12—O3	126.27 (16)	C9—C10—H102	109.5
O2—C12—C12i	116.79 (17)	C9—C10—H103	109.5
O3—C12—C12i	116.94 (17)	H101—C10—H102	109.5
C1—O1—H201	110.2	H101—C10—H103	109.5
C8—N1—H301	107.5	H102—C10—H103	109.5
C8—N1—H302	107.5	C9—C11—H111	109.5
C9—N1—H301	107.5	C9—C11—H112	109.5
C9—N1—H302	107.5	C9—C11—H113	109.5
H301—N1—H302	109.5	H111—C11—H112	109.5
O1—C1—H1	109.1	H111—C11—H113	109.5
C2—C1—H1	109.1	H112—C11—H113	109.5
C8—N1—C9—C10	68.7 (2)	C1—C2—C7—C6	179.3 (2)
C8—N1—C9—C11	−169.2 (2)	C3—C2—C7—C6	−0.7 (3)
C9—N1—C8—C1	96.3 (2)	C7—C2—C3—Cl1	−178.20 (17)
O1—C1—C2—C3	151.32 (19)	C7—C2—C3—C4	2.0 (3)
O1—C1—C2—C7	−28.6 (2)	Cl1—C3—C4—C5	178.38 (19)
O1—C1—C8—N1	−60.6 (2)	C2—C3—C4—C5	−1.8 (3)
C2—C1—C8—N1	177.85 (15)	C3—C4—C5—C6	0.2 (3)
C8—C1—C2—C3	−88.1 (2)	C4—C5—C6—C7	1.1 (4)
C8—C1—C2—C7	91.9 (2)	C5—C6—C7—C2	−0.9 (3)
C1—C2—C3—Cl1	1.9 (2)	O2—C12—C12i—O3i	−0.5 (2)
C1—C2—C3—C4	−177.9 (2)	O3—C12—C12i—O2i	0.5 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H201···O3ii	0.82	1.89	2.707 (2)	175
N1—H301···O2ii	0.86	1.96	2.816 (2)	179
N1—H302···O3	0.86	2.34	3.070 (2)	143
N1—H302···O2i	0.86	2.09	2.807 (2)	141
C6—H6···O1iii	0.93	2.56	3.433 (3)	156

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H201⋯O3i	0.82	1.89	2.707 (2)	175
N1—H301⋯O2i	0.86	1.96	2.816 (2)	179
N1—H302⋯O3	0.86	2.34	3.070 (2)	143
N1—H302⋯O2ii	0.86	2.09	2.807 (2)	141
C6—H6⋯O1iii	0.93	2.56	3.433 (3)	156

Symmetry codes: (i) ; (ii) ; (iii) .