N-[2-(2-Chloro­phen­yl)-2-hydroxy­ethyl]propan-2-aminium chloride

Song, B.-W.; Xie, L.-J.; Dong, L.-L.; Tang, Z.; Feng, H.

doi:10.1107/S1600536809031146

organic compounds

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ISSN: 2056-9890

Volume 65| Part 9| September 2009| Page o2187

doi:10.1107/S1600536809031146

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N-[2-(2-Chlorophenyl)-2-hydroxyethyl]propan-2-aminium chloride

Bi-Wei Song,^a Lin-Jun Xie,^b Ling-Ling Dong,^a Zhan Tang ^a and Hai Feng ^a ^*

^aCollege of Pharmaceutical Sciences, Zhejiang University of Technology, Hangzhou 310014, People's Republic of China, and ^bCollege of Mechanical Engineering, Zhejiang University of Technology, Hangzhou 310014, People's Republic of China
^*Correspondence e-mail: fenghai289289@163.com

(Received 1 August 2009; accepted 6 August 2009; online 19 August 2009)

In the title compound, C₁₁H₁₇ClNO⁺·Cl⁻, the side chain of the ethylamine group is orientated approximately perpendicular to the benzene ring, the dihedral angle between the C/C/N plane of the ethylamine group and the benzene plane being 83.5 (3)°. In the crystal structure, intermolecular 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_r = 250.16
Orthorhombic, P 2₁ 2₁ 2₁
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 (ABSCOR; 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[F² > 2σ(F²)] = 0.032
wR(F²) = 0.107
S = 1.00
2977 reflections
140 parameters
H-atom parameters constrained
Δρ_max = 0.29 e Å⁻³
Δρ_min = −0.29 e Å⁻³
Absolute structure: Flack (1983 ), 1243 Friedel pairs
Flack parameter: 0.51 (10)

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) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+1]$ ; (ii) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+1]$ .

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 ).

Supporting information

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

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

checkCIF report

Comment top

The title compound (clorprenaline hydrochloride) is one of a series of structurally related β-adrenoceptorblocking drugs.

In the molecular structure (Fig. 1), there are no unusual bond distances or angles. The Cl atom and the phenyl plane is almost planar with the deviation of 0.0037 Å. The dihedral angle between the plane formed by C7/C8/N1 and the phenyl plane is 83.5 (3)°, which shows that the two planes are almost perpendicular. The C9—N1 distance of 1.506 Å is longer than the value of the similar bond distance of 1.474 Å (Tang et al., 2009).

O—H···Cl and N—H···Cl hydrogen bonds are found in the crystal structure and are essential forces in crystal formation. The hydroxyl hydrogen at O1 acts as a donor to Cl2. The ethylamine hydrogens at N1 also act as donors to Cl2.

Related literature top

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

Experimental top

Racemic Clorprenaline hydrochloride was purchased from ShangHai Shengxin Medicine & Chemical Co., Ltd. ShangHai, China. Racemic Clorprenaline hydrochloride (5 g) was dissolved in ethanol (75 ml) and then hydrochloric acid was added to give pH of about 4. Colorless crystal of (I) separated from the solution in about 80% yield after one day.

Computing details top

Data collection: PROCESS-AUTO (Rigaku, 2006); cell refinement: PROCESS-AUTO (Rigaku, 2006); data reduction: CrystalStructure (Rigaku/MSC, 2007); program(s) used to solve structure: SHELXL97 (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).

Figures top

Fig. 1. The molecular structure of (I) with atom labels, showing 40% probability displacement ellipsoids.

N-[2-(2-Chlorophenyl)-2-hydroxyethyl]propan-2-aminium chloride top

Crystal data top

C₁₁H₁₇ClNO⁺·Cl⁻	F(000) = 528
M_r = 250.16	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0431P)² + 0.5P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.107	(Δ/σ)_max < 0.001
S = 1.00	Δρ_max = 0.29 e Å⁻³
2977 reflections	Δρ_min = −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	Absolute structure parameter: 0.51 (10)

Crystal data top

C₁₁H₁₇ClNO⁺·Cl⁻	V = 1317.72 (10) Å³
M_r = 250.16	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 7.3460 (3) Å	µ = 0.47 mm⁻¹
b = 11.7721 (5) Å	T = 296 K
c = 15.2377 (8) Å	0.40 × 0.36 × 0.32 mm

Data collection top

Rigaku R-AXIS RAPID diffractometer	2977 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	1874 reflections with I > 2σ(I)
T_min = 0.835, T_max = 0.864	R_int = 0.031
12577 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.032	H-atom parameters constrained
wR(F²) = 0.107	Δρ_max = 0.29 e Å⁻³
S = 1.00	Δρ_min = −0.29 e Å⁻³
2977 reflections	Absolute structure: Flack (1983), 1243 Friedel pairs
140 parameters	Absolute structure parameter: 0.51 (10)
0 restraints

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.

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.

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

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) x−1/2, −y+1/2, −z+1; (ii) x+1/2, −y+1/2, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₁H₁₇ClNO⁺·Cl⁻
M_r	250.16
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	296
a, b, c (Å)	7.3460 (3), 11.7721 (5), 15.2377 (8)
V (Å³)	1317.72 (10)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.47
Crystal size (mm)	0.40 × 0.36 × 0.32

Data collection
Diffractometer	Rigaku R-AXIS RAPID diffractometer
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995)
T_min, T_max	0.835, 0.864
No. of measured, independent and observed [I > 2σ(I)] reflections	12577, 2977, 1874
R_int	0.031
(sin θ/λ)_max (Å⁻¹)	0.648

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.032, 0.107, 1.00
No. of reflections	2977
No. of parameters	140
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.29, −0.29
Absolute structure	Flack (1983), 1243 Friedel pairs
Absolute structure parameter	0.51 (10)

Computer programs: PROCESS-AUTO (Rigaku, 2006), CrystalStructure (Rigaku/MSC, 2007), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

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) x−1/2, −y+1/2, −z+1; (ii) x+1/2, −y+1/2, −z+1.

References

Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. CrossRef CAS IUCr Journals Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan. Google Scholar
Rigaku (2006). PROCESS-AUTO. Rigaku Corporation, Tokyo, Japan. Google Scholar
Rigaku/MSC (2007). CrystalStructure. Rigaku/MSC. The Woodlands, Texas, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Tang, Z., Xu, M., Zheng, G.-R. & Feng, H. (2009). Acta Cryst. E65, o1501. Web of Science CSD CrossRef IUCr Journals Google Scholar

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doi:10.1107/S1600536809031146

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