1-(4-Amino-3,5-dichloro­phen­yl)ethanol

Liu, P.; Wu, J.-F.; Wang, P.-A.; He, W.; Wang, H.-B.

doi:10.1107/S1600536811024196

organic compounds

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ISSN: 2056-9890

Volume 67| Part 7| July 2011| Page o1839

doi:10.1107/S1600536811024196

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1-(4-Amino-3,5-dichlorophenyl)ethanol

Peng Liu,^a ^* Jian-Feng Wu,^a Ping-An Wang,^a Wei He ^a and Hai-Bo Wang ^a

^aDepartment of Chemistry, School of Pharmacy, Fourth Military Medical University, Changle West Road 169, 710032 Xi-An, People's Republic of China
^*Correspondence e-mail: pengliu@fmmu.edu.cn

(Received 1 June 2011; accepted 20 June 2011; online 30 June 2011)

The asymmetric unit of the title compound, C₈H₉Cl₂NO, contains two crystallographically independent molecules which are connected via an N—H⋯O hydrogen bond . There is aromatic π–π stacking in the crystal, with a centroid–centroid distance between benzene rings of 3.48 (2)Å. The crystal packing is stabilized by intermolecular hydrogen bonds.

Related literature

For the synthetic use of the title compound and related compounds, see: Judkins et al. (1991 ); Ehrhardt (1990 ); Kelser (2007 ); Lu (2001 ); Pri-Bar et al. (1990 ); Shukrallah et al. (2004 ).

Experimental

Crystal data

C₈H₉Cl₂NO
M_r = 206.06
Monoclinic, C 2/c
a = 16.472 (2) Å
b = 16.110 (2) Å
c = 14.6756 (19) Å
β = 107.049 (2)°
V = 3723.2 (8) Å³
Z = 16
Mo Kα radiation
μ = 0.65 mm⁻¹
T = 296 K
0.15 × 0.13 × 0.08 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2007 ) T_min = 0.909, T_max = 0.950
9273 measured reflections
3279 independent reflections
2855 reflections with I > 2σ(I)
R_int = 0.017

Refinement

R[F² > 2σ(F²)] = 0.032
wR(F²) = 0.128
S = 1.06
3279 reflections
277 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.42 e Å⁻³
Δρ_min = −0.46 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H13⋯O2ⁱ	0.82 (3)	2.17 (3)	2.927 (3)	154 (3)
O1—H16⋯N1ⁱⁱ	0.83 (3)	2.12 (3)	2.941 (3)	169 (3)
O2—H18⋯N2ⁱⁱⁱ	0.79 (3)	2.13 (3)	2.912 (3)	172 (2)
Symmetry codes: (i) $[x+1, -y, z+{\script{1\over 2}}]$ ; (ii) -x+2, -y, -z+2; (iii) -x+1, -y, -z+1.

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ) and Mercury (Macrae et al., 2006 ); software used to prepare material for publication: publCIF (Westrip, 2010).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811024196/zk2012sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811024196/zk2012Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811024196/zk2012Isup3.cml

checkCIF report

Comment top

We report here the crystal structure of the title compound 1-(4-amino-3, 5-dichlorophenyl) ethanol (I), a typical secondary aromatic alcohol and an important organic building block (Fig. 1). Bond lengths and angles are within normal ranges. As part of our ongoing studies of the secondary aromatic alcohol, the title compound was synthesized and characterized by X-ray diffraction. The asymmetric unit of the title compound (I) contains two crystallographically independent molecules in which both molecules are connected via N—H···O hydrogen bonds. The dihedral angle between the two benzene rings is 60.49°. The packing of molecules in the crystal structure is stabilized by intermolecular O—H···N hydrogen bonds.

Related literature top

For the synthetic use of the title compound and related compounds, see: Judkins et al. (1991); Ehrhardt (1990); Kelser (2007); Lu (2001); Pri-Bar et al. (1990); Shukrallah et al. (2004).

Experimental top

1-(4-amino-3,5-dichlorophenyl)ethanone (1.03 g,5 mmol) was dissolved in anhydrous methanol(25 ml) at room temperature, followed by addition of NaBH4(0.227 g, 6 mmol). The mixture was stirred vigorously at room temperature until TLC showed no ethanone. The solvent was evaporated to dryness under reduced pressure to obtain a crude product, which was purified by a flash column chromatography (n-hexane/EtOAc 8:1) to afford pure colorless compound in 89.6% yield. Then, the title compound (40 mg,0.19 mmol) was dissolved in ethyl acetate/n-hexane (7:3,15 ml). Colorless crystals were isolated after several days.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2006); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

Fig. 1. The molecular structure of the title compound, with atom labels and anisotropic displacement ellipsoids drawn at 50% probability level.

1-(4-Amino-3,5-dichlorophenyl)ethanol top

Crystal data top

C₈H₉Cl₂NO	F(000) = 1696
M_r = 206.06	D_x = 1.470 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 16.472 (2) Å	Cell parameters from 5355 reflections
b = 16.110 (2) Å	θ = 2.6–28.3°
c = 14.6756 (19) Å	µ = 0.65 mm⁻¹
β = 107.049 (2)°	T = 296 K
V = 3723.2 (8) Å³	Block, colorless
Z = 16	0.15 × 0.13 × 0.08 mm

Data collection top

Bruker APEXII CCD diffractometer	3279 independent reflections
Radiation source: fine-focus sealed tube	2855 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.017
ϕ and ω scans	θ_max = 25.0°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −19→15
T_min = 0.909, T_max = 0.950	k = −19→17
9273 measured reflections	l = −17→16

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.128	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ²(F_o²) + (0.1P)²] where P = (F_o² + 2F_c²)/3
3279 reflections	(Δ/σ)_max = 0.001
277 parameters	Δρ_max = 0.42 e Å⁻³
1 restraint	Δρ_min = −0.46 e Å⁻³

Crystal data top

C₈H₉Cl₂NO	V = 3723.2 (8) Å³
M_r = 206.06	Z = 16
Monoclinic, C2/c	Mo Kα radiation
a = 16.472 (2) Å	µ = 0.65 mm⁻¹
b = 16.110 (2) Å	T = 296 K
c = 14.6756 (19) Å	0.15 × 0.13 × 0.08 mm
β = 107.049 (2)°

Data collection top

Bruker APEXII CCD diffractometer	3279 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2007)	2855 reflections with I > 2σ(I)
T_min = 0.909, T_max = 0.950	R_int = 0.017
9273 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.032	1 restraint
wR(F²) = 0.128	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	Δρ_max = 0.42 e Å⁻³
3279 reflections	Δρ_min = −0.46 e Å⁻³
277 parameters

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	1.10844 (4)	0.04952 (4)	0.86690 (4)	0.0620 (2)
Cl2	1.09417 (4)	0.16958 (4)	1.20328 (4)	0.0598 (2)
Cl3	0.70719 (3)	−0.07065 (4)	0.67509 (4)	0.0557 (2)
Cl4	0.44673 (4)	0.14455 (3)	0.61899 (4)	0.0527 (2)
O1	0.78216 (11)	0.06516 (11)	0.85101 (13)	0.0617 (5)
O2	0.31701 (9)	−0.14705 (11)	0.48677 (12)	0.0519 (4)
N1	1.18071 (11)	0.10254 (12)	1.06839 (15)	0.0468 (4)
N2	0.63069 (12)	0.09603 (13)	0.67790 (13)	0.0440 (4)
C1	1.04879 (13)	0.08619 (12)	0.93915 (14)	0.0416 (5)
C2	0.96140 (14)	0.08983 (14)	0.90409 (15)	0.0458 (5)
C3	0.91343 (12)	0.11733 (12)	0.96181 (14)	0.0414 (5)
C4	0.95554 (13)	0.14186 (12)	1.05372 (15)	0.0408 (5)
C5	1.04275 (12)	0.13832 (12)	1.08668 (13)	0.0389 (4)
C6	1.09322 (12)	0.11026 (11)	1.03173 (13)	0.0375 (4)
C7	0.81676 (14)	0.12321 (15)	0.92535 (18)	0.0517 (5)
C8	0.78811 (16)	0.20783 (16)	0.8855 (2)	0.0712 (8)
H8A	0.7272	0.2094	0.8632	0.107*
H8B	0.8106	0.2193	0.8334	0.107*
H8C	0.8082	0.2489	0.9344	0.107*
C9	0.59864 (12)	−0.05077 (12)	0.64539 (13)	0.0377 (4)
C10	0.54210 (12)	−0.11507 (13)	0.61455 (14)	0.0388 (4)
C11	0.45556 (12)	−0.10121 (12)	0.58610 (13)	0.0380 (4)
C12	0.42693 (12)	−0.02043 (13)	0.58929 (14)	0.0406 (5)
C13	0.48443 (12)	0.04327 (12)	0.62044 (13)	0.0366 (4)
C14	0.57235 (11)	0.03095 (12)	0.65081 (12)	0.0354 (4)
C15	0.39451 (13)	−0.17286 (14)	0.55311 (16)	0.0458 (5)
C16	0.37270 (17)	−0.21407 (17)	0.6356 (2)	0.0578 (6)
H1	0.3668 (13)	−0.0092 (11)	0.5668 (14)	0.035 (5)*
H2	0.5640 (15)	−0.1665 (14)	0.6168 (17)	0.048 (6)*
H3	0.9238 (15)	0.1595 (14)	1.0923 (18)	0.048 (6)*
H4	0.4188 (13)	−0.2126 (14)	0.5260 (15)	0.045 (6)*
H5	0.9332 (14)	0.0707 (13)	0.8489 (16)	0.045 (6)*
H6	0.3307 (18)	−0.2551 (16)	0.612 (2)	0.069 (7)*
H8	0.6703 (16)	0.0815 (14)	0.7248 (17)	0.045 (6)*
H9	0.3513 (16)	−0.1676 (16)	0.6741 (18)	0.058 (7)*
H10	0.4207 (17)	−0.2342 (17)	0.6731 (19)	0.062 (7)*
H11	0.6117 (18)	0.1357 (18)	0.6943 (19)	0.061 (9)*
H12	0.7895 (15)	0.1125 (15)	0.9809 (17)	0.051 (6)*
H13	1.2082 (18)	0.1076 (17)	1.030 (2)	0.062 (8)*
H15	1.2046 (18)	0.1337 (17)	1.118 (2)	0.062 (8)*
H16	0.794 (2)	0.016 (2)	0.867 (2)	0.084 (10)*
H18	0.3276 (19)	−0.1363 (17)	0.4388 (16)	0.070 (9)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0664 (4)	0.0764 (4)	0.0496 (4)	0.0058 (3)	0.0267 (3)	−0.0065 (3)
Cl2	0.0441 (3)	0.0892 (5)	0.0391 (3)	0.0033 (3)	0.0011 (2)	−0.0144 (3)
Cl3	0.0275 (3)	0.0586 (4)	0.0742 (4)	0.0044 (2)	0.0044 (2)	−0.0059 (3)
Cl4	0.0508 (4)	0.0457 (3)	0.0588 (4)	0.0116 (2)	0.0116 (3)	−0.0049 (2)
O1	0.0475 (9)	0.0491 (10)	0.0669 (11)	−0.0050 (7)	−0.0171 (8)	−0.0017 (8)
O2	0.0332 (8)	0.0783 (11)	0.0422 (9)	−0.0106 (7)	0.0082 (6)	−0.0022 (7)
N1	0.0341 (9)	0.0582 (12)	0.0472 (11)	−0.0009 (8)	0.0106 (8)	−0.0004 (9)
N2	0.0387 (10)	0.0460 (10)	0.0430 (10)	−0.0016 (8)	0.0053 (8)	−0.0039 (8)
C1	0.0448 (11)	0.0432 (11)	0.0381 (10)	0.0021 (9)	0.0142 (9)	0.0011 (8)
C2	0.0463 (12)	0.0497 (12)	0.0345 (11)	−0.0036 (9)	0.0010 (9)	−0.0027 (9)
C3	0.0345 (10)	0.0410 (10)	0.0432 (11)	−0.0028 (8)	0.0027 (8)	0.0011 (8)
C4	0.0359 (11)	0.0431 (11)	0.0418 (11)	0.0021 (8)	0.0089 (9)	−0.0019 (8)
C5	0.0369 (10)	0.0421 (11)	0.0333 (10)	−0.0026 (8)	0.0033 (8)	−0.0008 (8)
C6	0.0337 (10)	0.0377 (10)	0.0395 (10)	0.0011 (7)	0.0082 (8)	0.0054 (8)
C7	0.0368 (11)	0.0531 (12)	0.0561 (13)	−0.0047 (9)	−0.0009 (10)	0.0000 (10)
C8	0.0454 (14)	0.0526 (14)	0.101 (2)	0.0025 (11)	−0.0017 (13)	0.0039 (13)
C9	0.0269 (9)	0.0488 (11)	0.0348 (10)	0.0023 (8)	0.0050 (7)	0.0024 (8)
C10	0.0365 (10)	0.0404 (11)	0.0379 (10)	0.0041 (8)	0.0086 (8)	0.0008 (8)
C11	0.0341 (10)	0.0448 (11)	0.0345 (10)	−0.0027 (8)	0.0094 (8)	−0.0022 (8)
C12	0.0282 (10)	0.0541 (12)	0.0383 (10)	0.0026 (8)	0.0081 (8)	−0.0010 (9)
C13	0.0363 (10)	0.0413 (10)	0.0323 (9)	0.0073 (8)	0.0101 (8)	0.0007 (8)
C14	0.0331 (10)	0.0432 (10)	0.0283 (9)	−0.0013 (8)	0.0068 (7)	0.0001 (8)
C15	0.0352 (11)	0.0500 (12)	0.0525 (13)	−0.0036 (9)	0.0132 (9)	−0.0109 (10)
C16	0.0518 (15)	0.0547 (14)	0.0610 (15)	−0.0106 (12)	0.0073 (12)	0.0077 (12)

Geometric parameters (Å, º) top

Cl1—C1	1.7463 (19)	C4—H3	0.92 (2)
Cl2—C5	1.7462 (19)	C5—C6	1.392 (3)
Cl3—C9	1.7415 (19)	C7—C8	1.504 (3)
Cl4—C13	1.7437 (19)	C7—H12	1.05 (2)
O1—C7	1.423 (3)	C8—H8A	0.9600
O1—H16	0.84 (3)	C8—H8B	0.9600
O2—C15	1.422 (3)	C8—H8C	0.9600
O2—H18	0.792 (17)	C9—C10	1.378 (3)
N1—C6	1.388 (3)	C9—C14	1.395 (3)
N1—H13	0.82 (3)	C10—C11	1.381 (3)
N1—H15	0.87 (3)	C10—H2	0.90 (2)
N2—C14	1.399 (3)	C11—C12	1.390 (3)
N2—H8	0.83 (3)	C11—C15	1.514 (3)
N2—H11	0.78 (3)	C12—C13	1.380 (3)
C1—C2	1.381 (3)	C12—H1	0.96 (2)
C1—C6	1.396 (3)	C13—C14	1.399 (3)
C2—C3	1.389 (3)	C15—C16	1.513 (3)
C2—H5	0.86 (2)	C15—H4	0.91 (2)
C3—C4	1.381 (3)	C16—H6	0.95 (3)
C3—C7	1.527 (3)	C16—H9	1.06 (3)
C4—C5	1.376 (3)	C16—H10	0.88 (3)

C7—O1—H16	113 (2)	H8A—C8—H8B	109.5
C15—O2—H18	106 (2)	C7—C8—H8C	109.5
C6—N1—H13	116 (2)	H8A—C8—H8C	109.5
C6—N1—H15	115.7 (18)	H8B—C8—H8C	109.5
H13—N1—H15	108 (3)	C10—C9—C14	122.46 (17)
C14—N2—H8	109.3 (16)	C10—C9—Cl3	119.32 (15)
C14—N2—H11	113 (2)	C14—C9—Cl3	118.18 (14)
H8—N2—H11	105 (3)	C9—C10—C11	121.09 (19)
C2—C1—C6	122.87 (18)	C9—C10—H2	117.1 (15)
C2—C1—Cl1	119.93 (16)	C11—C10—H2	121.8 (15)
C6—C1—Cl1	117.20 (15)	C10—C11—C12	118.14 (18)
C1—C2—C3	120.23 (19)	C10—C11—C15	120.22 (18)
C1—C2—H5	123.4 (15)	C12—C11—C15	121.64 (17)
C3—C2—H5	116.1 (15)	C13—C12—C11	120.04 (17)
C4—C3—C2	118.29 (18)	C13—C12—H1	120.7 (11)
C4—C3—C7	119.86 (19)	C11—C12—H1	119.2 (11)
C2—C3—C7	121.82 (18)	C12—C13—C14	123.08 (17)
C5—C4—C3	120.33 (19)	C12—C13—Cl4	118.96 (15)
C5—C4—H3	121.3 (15)	C14—C13—Cl4	117.93 (15)
C3—C4—H3	118.4 (15)	C9—C14—C13	115.17 (16)
C4—C5—C6	123.30 (18)	C9—C14—N2	121.63 (17)
C4—C5—Cl2	119.27 (15)	C13—C14—N2	123.02 (18)
C6—C5—Cl2	117.44 (15)	O2—C15—C16	107.45 (18)
N1—C6—C5	122.21 (18)	O2—C15—C11	112.01 (18)
N1—C6—C1	122.73 (18)	C16—C15—C11	111.70 (19)
C5—C6—C1	114.97 (17)	O2—C15—H4	109.2 (14)
O1—C7—C8	106.7 (2)	C16—C15—H4	106.3 (13)
O1—C7—C3	111.71 (19)	C11—C15—H4	109.9 (14)
C8—C7—C3	111.63 (19)	C15—C16—H6	109.3 (17)
O1—C7—H12	108.6 (13)	C15—C16—H9	108.2 (13)
C8—C7—H12	107.1 (13)	H6—C16—H9	112 (2)
C3—C7—H12	110.9 (13)	C15—C16—H10	106.3 (16)
C7—C8—H8A	109.5	H6—C16—H10	113 (2)
C7—C8—H8B	109.5	H9—C16—H10	108 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H13···O2ⁱ	0.82 (3)	2.17 (3)	2.927 (3)	154 (3)
O1—H16···N1ⁱⁱ	0.83 (3)	2.12 (3)	2.941 (3)	169 (3)
O2—H18···N2ⁱⁱⁱ	0.79 (3)	2.13 (3)	2.912 (3)	172 (2)

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

Experimental details

Crystal data
Chemical formula	C₈H₉Cl₂NO
M_r	206.06
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	296
a, b, c (Å)	16.472 (2), 16.110 (2), 14.6756 (19)
β (°)	107.049 (2)
V (Å³)	3723.2 (8)
Z	16
Radiation type	Mo Kα
µ (mm⁻¹)	0.65
Crystal size (mm)	0.15 × 0.13 × 0.08

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2007)
T_min, T_max	0.909, 0.950
No. of measured, independent and observed [I > 2σ(I)] reflections	9273, 3279, 2855
R_int	0.017
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.032, 0.128, 1.06
No. of reflections	3279
No. of parameters	277
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.42, −0.46

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2006), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H13···O2ⁱ	0.82 (3)	2.17 (3)	2.927 (3)	154 (3)
O1—H16···N1ⁱⁱ	0.83 (3)	2.12 (3)	2.941 (3)	169 (3)
O2—H18···N2ⁱⁱⁱ	0.79 (3)	2.13 (3)	2.912 (3)	172 (2)

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

Acknowledgements

We thank the Natural Science Foundation of China (grant No. 20802092,21072228, 81001398) for financial support.

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