1-(2-Chloro-phen-yl)-2-(isopropyl-amino)ethanol.

In the title compound, C(11)H(16)ClNO, the side chain of the ethyl-amine group is almost perpendicular to the benzene ring; the dihedral angle between the C/C/N plane of the ethyl-amine grouping and the benzene plane is 87.4 (2)°. An intramolecular N-H⋯O hydrogen bond occurs. In the crystal structure, mol-ecules are connected weakly by O-H⋯N hydrogen bonds, forming a tetra-mer around the symmetry axis. The tetra-mers 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 = 213.70

Tetragonal,

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 (; 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

Δρmax = 0.19 e Å−3

Δρmin = −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.

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

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

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

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

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 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)

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
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*

	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)

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)

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

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) .