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

Abstract

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 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,

• a = 14.0195 (5) Å

• c = 12.1243 (4) Å

• V = 2382.99 (14) ų

• 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[F ² > 2σ(F ²)] = 0.043

• wR(F ²) = 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)

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.

Supplementary Material

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

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) ; (ii) .

supplementary crystallographic information

Comment

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).

Experimental

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.

Refinement

H atoms were placed in calculated positions and allowed to ride on their parent atoms with C—H = 0.93 (aromatic), 0.98 (methine), 0.97 (methylene), 0.96 (methyl), O—H = 0.82 and N—H = 0.858 Å, with U_iso(H) = 1.2 or 1.5 times U_eq of the parent atoms.

Figures

Fig. 1.

The molecular structure with atom labels, showing 40% probability displacement ellipsoids.

Fig. 2.

A packing diagram, viewed down along the c axis.

Crystal data

C11H16ClNO	Dx = 1.191 Mg m−3
Mr = 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

Rigaku R-AXIS RAPID diffractometer	2711 independent reflections
Radiation source: RT	1796 reflections with I > 2σ(I)
graphite	Rint = 0.044
Detector resolution: 10.00 pixels mm-1	θmax = 27.4°, θmin = 3.3°
ω scans	h = −18→17
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	k = −18→18
Tmin = 0.871, Tmax = 0.939	l = −13→15
22063 measured reflections

Refinement

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(Fo2) + (0.002P)2 + 1.96P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.098	(Δ/σ)max < 0.001
S = 1.00	Δρmax = 0.19 e Å−3
2711 reflections	Δρmin = −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	Flack parameter: 0.001 (1)

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
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 (Ų)

	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, °)

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, °)

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.