1-(2-Chloro­phen­yl)-2-(isopropyl­amino)ethanol

Tang, Z.; Xu, M.; Zheng, G.-R.; Feng, H.

doi:10.1107/S1600536809019953

organic compounds

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ISSN: 2056-9890

Volume 65| Part 7| July 2009| Page o1501

doi:10.1107/S1600536809019953

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1-(2-Chlorophenyl)-2-(isopropylamino)ethanol

Zhan Tang,^a Min Xu,^a Gui-Ru Zheng ^b and Hai Feng ^a ^*

^aCollege of Pharmaceutical Sciences, Zhejiang University of Technology, Hangzhou 310014, People's Republic of China, and ^bJinhua People's Hospital, Jinhua 321000, People's Republic of China
^*Correspondence e-mail: fenghai289289@163.com

(Received 30 April 2009; accepted 26 May 2009; online 6 June 2009)

In the title compound, C₁₁H₁₆ClNO, the side chain of the ethylamine group is almost perpendicular to the benzene ring; the dihedral angle between the C/C/N plane of the ethylamine grouping and the benzene plane is 87.4 (2)°. An intramolecular N—H⋯O hydrogen bond occurs. In the crystal structure, molecules are connected weakly by O—H⋯N hydrogen bonds, forming a tetramer around the $[\overline{4}]$ symmetry axis. The tetramers are linked weakly by a C—H⋯O hydrogen bond.

Related literature

For a related structure, see: Koorts & Caira (1985 ). For the synthesis of the title compound, see; Koshinaka et al. (1978 ).

Experimental

Crystal data

C₁₁H₁₆ClNO
M_r = 213.70
Tetragonal, $[P \overline 42_1 c ]$
a = 14.0195 (5) Å
c = 12.1243 (4) Å
V = 2382.99 (14) Å³
Z = 8
Mo Kα radiation
μ = 0.29 mm⁻¹
T = 296 K
0.41 × 0.38 × 0.22 mm

Data collection

Rigaku R-AXIS RAPID diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ) T_min = 0.871, T_max = 0.939
22063 measured reflections
2711 independent reflections
1796 reflections with I > 2σ(I)
R_int = 0.044

Refinement

R[F² > 2σ(F²)] = 0.043
wR(F²) = 0.098
S = 1.00
2711 reflections
131 parameters
H-atom parameters constrained
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.33 e Å⁻³
Absolute structure: Flack (1983 ), 1181 Friedel pairs
Flack parameter: 0.001 (1)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H201⋯N1ⁱ	0.82	1.97	2.765 (3)	164
N1—H301⋯O1	0.86	2.25	2.789 (3)	121
C6—H6⋯O1ⁱⁱ	0.93	2.45	3.283 (4)	149
Symmetry codes: (i) y, -x+2, -z+1; (ii) $[y-{\script{1\over 2}}, x+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: PROCESS-AUTO (Rigaku, 1998 ); 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: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809019953/is2416sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809019953/is2416Isup2.hkl

checkCIF report

Comment top

The title compound (clorprenaline) is one of a series of structurally related β-adrenoceptorblocking drugs. Synthesis results have been reported in the literature (Koshinaka et al., 1978). Clorprenaline was prepared by clorprenaline hydrochloride.

In the title compound (Fig. 1), there are no unusual bond distances or angles. The Cl atom and the phenyl plane is almost planar with the deviation of 0.0026 Å. The dihedral angle between the plane formed by C1 C2 C8 and the phenyl plane is 87.5°, which shows that the two planes are almost perpendicular. The C9—N1 distance of 1.473 (4) Å is shorter than the value of the similar bond distance of 1.502 Å (Koorts & Caira, 1985). The crystal structure indicates a possible intermolecular O—H···N interaction that might help to establish the crystal packing (Fig. 2).

Related literature top

For a related structure, see: Koorts & Caira (1985). For the synthesis of 1-(2-chlorophenyl)-2-(isopropylamino)ethanol hydrochloride, see; Koshinaka et al. (1978).

Experimental top

Racemic clorprenaline hydrochloride (10 g, 0.047 mol), which was purchased from Hangzhou Chempro Tech Co., Inc. Hang Zhou, China, was dissolved in ethanol (100 ml) and NaOH (1.9 g, 0.047 mol) was dissolved in water (100 ml). The two solutions were mixed and the mixture was cooled for 3 h. The precipitate formed was filtered off, washed with water and dried. The crude product obtained was recrystallized from ethanol. Single crystals suitable for X-ray analysis were grown by slow evaporation at room temperature.

Computing details top

Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO (Rigaku, 1998); 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: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure with atom labels, showing 40% probability displacement ellipsoids.
	Fig. 2. A packing diagram, viewed down along the c axis.

1-(2-Chlorophenyl)-2-(isopropylamino)ethanol top

Crystal data top

C₁₁H₁₆ClNO	D_x = 1.191 Mg m⁻³
M_r = 213.70	Mo Kα radiation, λ = 0.71073 Å
Tetragonal, P42₁c	Cell parameters from 13301 reflections
Hall symbol: P -4 2n	θ = 3.3–27.4°
a = 14.0195 (5) Å	µ = 0.29 mm⁻¹
c = 12.1243 (4) Å	T = 296 K
V = 2382.99 (14) Å³	Block, colorless
Z = 8	0.41 × 0.38 × 0.22 mm
F(000) = 912

Data collection top

Rigaku R-AXIS RAPID diffractometer	2711 independent reflections
Radiation source: RT	1796 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.044
Detector resolution: 10.00 pixels mm^-1	θ_max = 27.4°, θ_min = 3.3°
ω scans	h = −18→17
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	k = −18→18
T_min = 0.871, T_max = 0.939	l = −13→15
22063 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)] = 0.043	w = 1/[σ²(F_o²) + (0.002P)² + 1.96P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.098	(Δ/σ)_max < 0.001
S = 1.00	Δρ_max = 0.19 e Å⁻³
2711 reflections	Δρ_min = −0.33 e Å⁻³
131 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.0308 (10)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 1181 Friedel pairs
Secondary atom site location: difference Fourier map	Absolute structure parameter: 0.001 (1)

Crystal data top

C₁₁H₁₆ClNO	Z = 8
M_r = 213.70	Mo Kα radiation
Tetragonal, P42₁c	µ = 0.29 mm⁻¹
a = 14.0195 (5) Å	T = 296 K
c = 12.1243 (4) Å	0.41 × 0.38 × 0.22 mm
V = 2382.99 (14) Å³

Data collection top

Rigaku R-AXIS RAPID diffractometer	2711 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	1796 reflections with I > 2σ(I)
T_min = 0.871, T_max = 0.939	R_int = 0.044
22063 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.043	H-atom parameters constrained
wR(F²) = 0.098	Δρ_max = 0.19 e Å⁻³
S = 1.00	Δρ_min = −0.33 e Å⁻³
2711 reflections	Absolute structure: Flack (1983), 1181 Friedel pairs
131 parameters	Absolute structure parameter: 0.001 (1)
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
Cl1	0.89802 (8)	0.90968 (7)	0.76779 (8)	0.0866 (3)
O1	0.82940 (16)	1.14673 (15)	0.54268 (18)	0.0616 (6)
H201	0.8801	1.1727	0.5581	0.074*
C2	0.81036 (19)	1.07851 (19)	0.7258 (2)	0.0484 (6)
C1	0.8209 (2)	1.06095 (19)	0.6030 (2)	0.0492 (7)
H1	0.8769	1.0208	0.5896	0.059*
N1	0.74199 (17)	0.99152 (18)	0.4402 (2)	0.0527 (6)
H301	0.7679	1.0439	0.4192	0.063*
C4	0.8307 (3)	1.0339 (3)	0.9173 (3)	0.0717 (10)
H4	0.8532	0.9910	0.9697	0.086*
C3	0.8417 (2)	1.0153 (2)	0.8060 (2)	0.0557 (7)
C8	0.7325 (2)	1.0115 (2)	0.5591 (2)	0.0538 (7)
H8A	0.7227	0.9521	0.5987	0.065*
H8B	0.6772	1.0517	0.5714	0.065*
C9	0.6502 (2)	0.9762 (2)	0.3839 (3)	0.0658 (9)
H9	0.6062	1.0272	0.4054	0.079*
C7	0.7657 (2)	1.1617 (2)	0.7621 (3)	0.0649 (8)
H7	0.7436	1.2054	0.7104	0.078*
C11	0.6655 (3)	0.9809 (3)	0.2604 (3)	0.0907 (12)
H11A	0.7094	0.9319	0.2385	0.109*
H11B	0.6911	1.0422	0.2411	0.109*
H11C	0.6057	0.9717	0.2233	0.109*
C6	0.7534 (2)	1.1809 (3)	0.8735 (3)	0.0753 (10)
H6	0.7233	1.2367	0.8959	0.090*
C10	0.6073 (3)	0.8813 (3)	0.4176 (3)	0.0885 (12)
H10A	0.5965	0.8810	0.4958	0.106*
H10B	0.6505	0.8307	0.3986	0.106*
H10C	0.5479	0.8721	0.3798	0.106*
C5	0.7860 (3)	1.1172 (3)	0.9497 (3)	0.0779 (11)
H5	0.7781	1.1300	1.0244	0.093*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.1254 (9)	0.0656 (5)	0.0688 (5)	0.0248 (5)	−0.0095 (6)	0.0035 (5)
O1	0.0652 (14)	0.0607 (13)	0.0588 (12)	−0.0115 (10)	−0.0115 (11)	0.0144 (10)
C2	0.0470 (14)	0.0513 (15)	0.0470 (14)	−0.0033 (12)	0.0018 (13)	−0.0009 (13)
C1	0.0505 (16)	0.0506 (16)	0.0466 (15)	0.0013 (13)	−0.0003 (13)	0.0046 (12)
N1	0.0532 (14)	0.0547 (14)	0.0501 (13)	−0.0047 (12)	−0.0052 (11)	−0.0027 (12)
C4	0.086 (3)	0.082 (3)	0.0473 (18)	−0.006 (2)	−0.0079 (17)	−0.0014 (16)
C3	0.0620 (18)	0.0542 (17)	0.0509 (16)	−0.0040 (15)	−0.0033 (14)	0.0002 (13)
C8	0.0536 (17)	0.0556 (17)	0.0522 (16)	−0.0052 (14)	0.0036 (14)	−0.0057 (14)
C9	0.0605 (19)	0.062 (2)	0.075 (2)	0.0040 (16)	−0.0155 (17)	−0.0085 (16)
C7	0.0632 (19)	0.0651 (19)	0.066 (2)	0.0135 (15)	0.0028 (17)	−0.0066 (17)
C11	0.106 (3)	0.092 (3)	0.074 (2)	0.004 (2)	−0.032 (2)	−0.007 (2)
C6	0.065 (2)	0.086 (3)	0.075 (2)	0.0079 (19)	0.0035 (19)	−0.025 (2)
C10	0.070 (2)	0.085 (3)	0.110 (3)	−0.021 (2)	−0.011 (2)	−0.007 (2)
C5	0.075 (2)	0.104 (3)	0.0548 (19)	−0.012 (2)	0.0057 (18)	−0.025 (2)

Geometric parameters (Å, º) top

Cl1—C3	1.741 (3)	C8—H8B	0.9700
O1—C1	1.413 (3)	C9—C10	1.516 (5)
O1—H201	0.8200	C9—C11	1.514 (5)
C2—C3	1.387 (4)	C9—H9	0.9800
C2—C7	1.395 (4)	C7—C6	1.387 (5)
C2—C1	1.516 (4)	C7—H7	0.9300
C1—C8	1.517 (4)	C11—H11A	0.9600
C1—H1	0.9800	C11—H11B	0.9600
N1—C9	1.473 (4)	C11—H11C	0.9600
N1—C8	1.475 (4)	C6—C5	1.364 (5)
N1—H301	0.8580	C6—H6	0.9300
C4—C5	1.382 (5)	C10—H10A	0.9600
C4—C3	1.383 (4)	C10—H10B	0.9600
C4—H4	0.9300	C10—H10C	0.9600
C8—H8A	0.9700	C5—H5	0.9300

C1—O1—H201	109.5	N1—C9—C11	109.2 (3)
C3—C2—C7	117.1 (3)	C10—C9—C11	111.2 (3)
C3—C2—C1	123.6 (3)	N1—C9—H9	108.7
C7—C2—C1	119.3 (3)	C10—C9—H9	108.7
O1—C1—C8	106.1 (2)	C11—C9—H9	108.7
O1—C1—C2	112.2 (2)	C6—C7—C2	121.7 (3)
C8—C1—C2	109.8 (2)	C6—C7—H7	119.2
O1—C1—H1	109.6	C2—C7—H7	119.2
C8—C1—H1	109.6	C9—C11—H11A	109.5
C2—C1—H1	109.6	C9—C11—H11B	109.5
C9—N1—C8	113.7 (2)	H11A—C11—H11B	109.5
C9—N1—H301	110.9	C9—C11—H11C	109.5
C8—N1—H301	99.5	H11A—C11—H11C	109.5
C5—C4—C3	119.2 (3)	H11B—C11—H11C	109.5
C5—C4—H4	120.4	C5—C6—C7	119.4 (3)
C3—C4—H4	120.4	C5—C6—H6	120.3
C4—C3—C2	121.9 (3)	C7—C6—H6	120.3
C4—C3—Cl1	118.1 (3)	C9—C10—H10A	109.5
C2—C3—Cl1	120.0 (2)	C9—C10—H10B	109.5
N1—C8—C1	110.9 (2)	H10A—C10—H10B	109.5
N1—C8—H8A	109.5	C9—C10—H10C	109.5
C1—C8—H8A	109.5	H10A—C10—H10C	109.5
N1—C8—H8B	109.5	H10B—C10—H10C	109.5
C1—C8—H8B	109.5	C6—C5—C4	120.8 (3)
H8A—C8—H8B	108.1	C6—C5—H5	119.6
N1—C9—C10	110.5 (3)	C4—C5—H5	119.6

C3—C2—C1—O1	−150.5 (3)	C9—N1—C8—C1	−159.3 (3)
C7—C2—C1—O1	30.5 (4)	O1—C1—C8—N1	59.9 (3)
C3—C2—C1—C8	91.8 (3)	C2—C1—C8—N1	−178.6 (2)
C7—C2—C1—C8	−87.2 (3)	C8—N1—C9—C10	−71.4 (4)
C5—C4—C3—C2	1.0 (5)	C8—N1—C9—C11	166.0 (3)
C5—C4—C3—Cl1	−179.8 (3)	C3—C2—C7—C6	0.3 (5)
C7—C2—C3—C4	−0.9 (5)	C1—C2—C7—C6	179.4 (3)
C1—C2—C3—C4	−180.0 (3)	C2—C7—C6—C5	0.2 (5)
C7—C2—C3—Cl1	179.9 (2)	C7—C6—C5—C4	−0.2 (6)
C1—C2—C3—Cl1	0.9 (4)	C3—C4—C5—C6	−0.4 (6)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H201···N1ⁱ	0.82	1.97	2.765 (3)	164
N1—H301···O1	0.86	2.25	2.789 (3)	121
C6—H6···O1ⁱⁱ	0.93	2.45	3.283 (4)	149

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

Experimental details

Crystal data
Chemical formula	C₁₁H₁₆ClNO
M_r	213.70
Crystal system, space group	Tetragonal, P42₁c
Temperature (K)	296
a, c (Å)	14.0195 (5), 12.1243 (4)
V (Å³)	2382.99 (14)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.29
Crystal size (mm)	0.41 × 0.38 × 0.22

Data collection
Diffractometer	Rigaku R-AXIS RAPID diffractometer
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995)
T_min, T_max	0.871, 0.939
No. of measured, independent and observed [I > 2σ(I)] reflections	22063, 2711, 1796
R_int	0.044
(sin θ/λ)_max (Å⁻¹)	0.648

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.043, 0.098, 1.00
No. of reflections	2711
No. of parameters	131
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.19, −0.33
Absolute structure	Flack (1983), 1181 Friedel pairs
Absolute structure parameter	0.001 (1)

Computer programs: PROCESS-AUTO (Rigaku, 1998), CrystalStructure (Rigaku/MSC, 2004), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H201···N1ⁱ	0.82	1.97	2.765 (3)	164
N1—H301···O1	0.86	2.25	2.789 (3)	121
C6—H6···O1ⁱⁱ	0.93	2.45	3.283 (4)	149

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

References

Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115–119. Web of Science CrossRef CAS IUCr Journals Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef 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
Koorts, J. & Caira, M. (1985). Acta Cryst. C41, 1372–1374. CSD CrossRef CAS Web of Science IUCr Journals Google Scholar
Koshinaka, E., Kurata, S., Yamagishi, K., Kubo, S. & Kato, H. (1978). Yakugaku Zasshi, 98, 1198–1207. CAS PubMed Web of Science Google Scholar
Rigaku (1998). PROCESS-AUTO. Rigaku Corporation, Tokyo, Japan. Google Scholar
Rigaku/MSC (2004). 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

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doi:10.1107/S1600536809019953

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