1-(Isopropyl­amino)-3-phen­oxy­propan-2-ol

Hou, X.; Li, Z.; Lv, Q.

doi:10.1107/S1600536812000566

organic compounds

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ISSN: 2056-9890

Volume 68| Part 2| February 2012| Page o359

doi:10.1107/S1600536812000566

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1-(Isopropylamino)-3-phenoxypropan-2-ol

Xuehui Hou,^a Zigang Li ^a and Quanjian Lv ^a ^*

^aDepartment of Quality Detection and Management, Zhengzhou College of Animal Husbandry Engineering, Zhengzhou 450011, People's Republic of China
^*Correspondence e-mail: jyzhang2004@126.com

(Received 15 November 2011; accepted 6 January 2012; online 11 January 2012)

In the crystal structure of the title amino alcohol derivitive, C₁₂H₁₉NO₂, molecules are linked by N—H⋯O hydrogen bonds. The molecular structure exhibits an intramolecular O—H⋯N hydrogen bond.

Related literature

For applications of amino alcohols and their derivatives, see: Ellison et al. (2005 ); Li et al. (2004 ).

Experimental

Crystal data

C₁₂H₁₉NO₂
M_r = 209.28
Tetragonal, $[P \overline 42_1 c ]$
a = 15.1162 (17) Å
c = 10.9448 (14) Å
V = 2500.9 (5) Å³
Z = 8
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 298 K
0.45 × 0.38 × 0.37 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.967, T_max = 0.973
9624 measured reflections
1252 independent reflections
676 reflections with I > 2σ(I)
R_int = 0.125

Refinement

R[F² > 2σ(F²)] = 0.064
wR(F²) = 0.221
S = 1.16
1252 reflections
138 parameters
16 restraints
H-atom parameters constrained
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.25 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯N1	0.82	2.31	2.760 (7)	115
N1—H1⋯O2ⁱ	0.90	1.84	2.742 (7)	179
Symmetry code: (i) -y+1, x, -z+1.

Data collection: SMART (Siemens, 1996 ); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008) and DIAMOND (Brandenburg, 1998 ); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812000566/lx2213sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812000566/lx2213Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812000566/lx2213Isup3.cml

checkCIF report

Comment top

Amino alcohols are important structural elements for asymmetric catalysis(Li et al., 2004) as well as in biologically active compounds(Ellison et al., 2005). In order to develop new applications for amino alcohols and their derivatives, structural modifications of these compounds have been extensively investigated. As a contribution in this filed, we report here the crystal structure of the title compound.

The molecular structure of the title compound is shown in Fig.1.

The title compound crystallizes as the non–centrosymmetric space group P _-421_c in spite of having no asymmetric C atoms.

The crystal packing (Fig. 2) is stabilized by intermolecular N—H···O hydrogen bonds (see, Table 1; second entry). The crystal packing (Fig. 2) is further stabilized by intramolecular O—H···N hydrogen bonds (see, Table 1; first entry).

Related literature top

For applications of amino alcohols and their derivatives, see: Ellison et al. (2005); Li et al. (2004).

Experimental top

To a solution of 2-(phenoxymethyl)oxirane (15.0 g, 0.1 mol) in acetone (200 ml), propan–2–amine (86.7 ml, 1.0 mol) was added. The mixture was stirred at room temperature for 6 h, followed by concentrated under reduced pressure and purification by crystallization from ethyl acetate, giving title compound as colourless single crystals suitabl for X-1ray analysis.

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008) and DIAMOND (Brandenburg, 1998); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound with the atom numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are presented as small spheres of arbitrary radius.
	Fig. 2. A view of the N—H···O and O—H···N hydrogen bonds (dotted lines) in the crystal structure of the title compound. [Symmetry codes: (i) - y + 1, x, - z + 1 (ii) y, - x + 1, - z + 1 (iii) - x + 1, - y + 1, z. ]

1-(Isopropylamino)-3-phenoxypropan-2-ol top

Crystal data top

C₁₂H₁₉NO₂	D_x = 1.112 Mg m⁻³
M_r = 209.28	Mo Kα radiation, λ = 0.71073 Å
Tetragonal, P42₁c	Cell parameters from 2006 reflections
Hall symbol: P -4 2n	θ = 2.3–19.8°
a = 15.1162 (17) Å	µ = 0.08 mm⁻¹
c = 10.9448 (14) Å	T = 298 K
V = 2500.9 (5) Å³	Block, colourless
Z = 8	0.45 × 0.38 × 0.37 mm
F(000) = 912

Data collection top

Bruker SMART CCD diffractometer	1252 independent reflections
Radiation source: fine-focus sealed tube	676 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.125
Detector resolution: 10.0 pixels mm^-1	θ_max = 25.0°, θ_min = 1.9°
ϕ and ω scans	h = −17→17
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −17→9
T_min = 0.967, T_max = 0.973	l = −7→13
9624 measured reflections

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)] = 0.064	Hydrogen site location: difference Fourier map
wR(F²) = 0.221	H-atom parameters constrained
S = 1.16	w = 1/[σ²(F_o²) + (0.0662P)² + 2.183P] where P = (F_o² + 2F_c²)/3
1252 reflections	(Δ/σ)_max < 0.001
138 parameters	Δρ_max = 0.24 e Å⁻³
16 restraints	Δρ_min = −0.25 e Å⁻³

Crystal data top

C₁₂H₁₉NO₂	Z = 8
M_r = 209.28	Mo Kα radiation
Tetragonal, P42₁c	µ = 0.08 mm⁻¹
a = 15.1162 (17) Å	T = 298 K
c = 10.9448 (14) Å	0.45 × 0.38 × 0.37 mm
V = 2500.9 (5) Å³

Data collection top

Bruker SMART CCD diffractometer	1252 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	676 reflections with I > 2σ(I)
T_min = 0.967, T_max = 0.973	R_int = 0.125
9624 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.064	16 restraints
wR(F²) = 0.221	H-atom parameters constrained
S = 1.16	Δρ_max = 0.24 e Å⁻³
1252 reflections	Δρ_min = −0.25 e Å⁻³
138 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
O1	0.5032 (3)	0.6282 (4)	0.7225 (4)	0.0824 (15)
O2	0.3665 (3)	0.6526 (3)	0.5499 (4)	0.0750 (14)
H2	0.3250	0.6451	0.5027	0.090*
N1	0.2523 (3)	0.5115 (4)	0.5235 (5)	0.0700 (17)
H1	0.2831	0.4635	0.4999	0.084*
C1	0.4135 (5)	0.6047 (5)	0.7440 (7)	0.074 (2)
H1C	0.3813	0.6547	0.7774	0.089*
H1D	0.4101	0.5561	0.8016	0.089*
C2	0.3755 (5)	0.5783 (5)	0.6253 (7)	0.0639 (17)
H2A	0.4151	0.5357	0.5858	0.077*
C3	0.2859 (4)	0.5375 (5)	0.6394 (7)	0.0650 (19)
H3A	0.2898	0.4863	0.6925	0.078*
H3B	0.2459	0.5798	0.6768	0.078*
C4	0.1582 (5)	0.4884 (6)	0.5218 (7)	0.099 (3)
H4	0.1242	0.5369	0.5583	0.119*
C5	0.1313 (6)	0.4781 (9)	0.3916 (9)	0.145 (5)
H5A	0.1431	0.5319	0.3481	0.218*
H5B	0.0692	0.4650	0.3874	0.218*
H5C	0.1642	0.4305	0.3553	0.218*
C6	0.1420 (7)	0.4060 (7)	0.5930 (11)	0.152 (5)
H6A	0.1765	0.3586	0.5592	0.228*
H6B	0.0804	0.3909	0.5890	0.228*
H6C	0.1588	0.4152	0.6766	0.228*
C7	0.5482 (4)	0.6682 (5)	0.8129 (7)	0.072 (2)
C8	0.5118 (5)	0.6915 (5)	0.9248 (6)	0.083 (2)
H8	0.4530	0.6790	0.9430	0.100*
C9	0.5660 (6)	0.7339 (5)	1.0086 (8)	0.099 (3)
H9	0.5437	0.7495	1.0848	0.119*
C10	0.6534 (6)	0.7533 (6)	0.9800 (11)	0.111 (4)
H10	0.6886	0.7831	1.0362	0.133*
C11	0.6867 (7)	0.7298 (5)	0.8730 (10)	0.103 (3)
H11	0.7458	0.7418	0.8563	0.124*
C12	0.6357 (4)	0.6876 (5)	0.7852 (8)	0.086 (2)
H12	0.6596	0.6727	0.7096	0.103*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.056 (3)	0.109 (4)	0.082 (3)	−0.016 (3)	−0.003 (3)	−0.020 (3)
O2	0.067 (3)	0.077 (3)	0.081 (3)	0.001 (3)	−0.007 (3)	0.005 (3)
N1	0.048 (3)	0.070 (4)	0.092 (4)	−0.002 (3)	−0.002 (3)	−0.025 (4)
C1	0.056 (4)	0.088 (5)	0.078 (5)	−0.013 (4)	0.005 (4)	−0.009 (4)
C2	0.056 (4)	0.064 (4)	0.072 (4)	0.001 (3)	−0.005 (4)	−0.003 (4)
C3	0.057 (4)	0.062 (4)	0.076 (5)	−0.008 (3)	0.001 (4)	−0.009 (4)
C4	0.048 (4)	0.110 (7)	0.139 (8)	−0.012 (4)	−0.004 (5)	−0.040 (7)
C5	0.075 (6)	0.211 (13)	0.150 (9)	−0.007 (8)	−0.041 (7)	−0.060 (9)
C6	0.102 (8)	0.157 (10)	0.196 (13)	−0.066 (7)	0.020 (8)	−0.001 (10)
C7	0.067 (5)	0.066 (5)	0.082 (5)	−0.004 (4)	−0.011 (4)	−0.002 (4)
C8	0.089 (6)	0.080 (5)	0.080 (5)	−0.011 (5)	−0.015 (5)	0.012 (5)
C9	0.125 (8)	0.079 (6)	0.093 (6)	−0.005 (6)	−0.030 (6)	−0.001 (5)
C10	0.129 (10)	0.077 (6)	0.127 (9)	−0.017 (6)	−0.051 (8)	−0.007 (6)
C11	0.091 (7)	0.078 (6)	0.141 (9)	−0.024 (5)	−0.042 (7)	−0.001 (7)
C12	0.065 (5)	0.081 (5)	0.113 (6)	−0.011 (4)	−0.011 (5)	0.003 (5)

Geometric parameters (Å, º) top

O1—C7	1.344 (8)	C5—H5A	0.9600
O1—C1	1.422 (8)	C5—H5B	0.9600
O2—C2	1.400 (8)	C5—H5C	0.9600
O2—H2	0.8200	C6—H6A	0.9600
N1—C3	1.422 (9)	C6—H6B	0.9600
N1—C4	1.464 (9)	C6—H6C	0.9600
N1—H1	0.9000	C7—C8	1.388 (2)
C1—C2	1.475 (9)	C7—C12	1.388 (2)
C1—H1C	0.9700	C8—C9	1.388 (2)
C1—H1D	0.9700	C8—H8	0.9300
C2—C3	1.497 (9)	C9—C10	1.388 (2)
C2—H2A	0.9800	C9—H9	0.9300
C3—H3A	0.9700	C10—C11	1.323 (13)
C3—H3B	0.9700	C10—H10	0.9300
C4—C5	1.490 (8)	C11—C12	1.388 (2)
C4—C6	1.490 (8)	C11—H11	0.9300
C4—H4	0.9800	C12—H12	0.9300

C7—O1—C1	118.3 (6)	C4—C5—H5B	109.5
C2—O2—H2	109.5	H5A—C5—H5B	109.5
C3—N1—C4	115.1 (6)	C4—C5—H5C	109.5
C3—N1—H1	107.1	H5A—C5—H5C	109.5
C4—N1—H1	107.9	H5B—C5—H5C	109.5
O1—C1—C2	107.1 (6)	C4—C6—H6A	109.5
O1—C1—H1C	110.3	C4—C6—H6B	109.5
C2—C1—H1C	110.3	H6A—C6—H6B	109.5
O1—C1—H1D	110.3	C4—C6—H6C	109.5
C2—C1—H1D	110.3	H6A—C6—H6C	109.5
H1C—C1—H1D	108.6	H6B—C6—H6C	109.5
O2—C2—C1	109.9 (6)	O1—C7—C8	124.3 (6)
O2—C2—C3	107.7 (6)	O1—C7—C12	114.6 (6)
C1—C2—C3	111.9 (6)	C8—C7—C12	121.1 (7)
O2—C2—H2A	109.1	C7—C8—C9	117.8 (7)
C1—C2—H2A	109.1	C7—C8—H8	121.1
C3—C2—H2A	109.1	C9—C8—H8	121.1
N1—C3—C2	110.2 (6)	C10—C9—C8	120.6 (8)
N1—C3—H3A	109.6	C10—C9—H9	119.7
C2—C3—H3A	109.6	C8—C9—H9	119.7
N1—C3—H3B	109.6	C11—C10—C9	120.4 (10)
C2—C3—H3B	109.6	C11—C10—H10	119.8
H3A—C3—H3B	108.1	C9—C10—H10	119.8
N1—C4—C5	107.6 (7)	C10—C11—C12	121.7 (10)
N1—C4—C6	110.6 (7)	C10—C11—H11	119.2
C5—C4—C6	111.5 (10)	C12—C11—H11	119.2
N1—C4—H4	109.0	C11—C12—C7	118.4 (8)
C5—C4—H4	109.0	C11—C12—H12	120.8
C6—C4—H4	109.0	C7—C12—H12	120.8
C4—C5—H5A	109.5

C7—O1—C1—C2	169.4 (6)	C1—O1—C7—C12	179.0 (7)
O1—C1—C2—O2	−70.2 (8)	O1—C7—C8—C9	−178.9 (7)
O1—C1—C2—C3	170.2 (6)	C12—C7—C8—C9	−0.6 (12)
C4—N1—C3—C2	−167.4 (6)	C7—C8—C9—C10	0.9 (13)
O2—C2—C3—N1	60.3 (7)	C8—C9—C10—C11	−1.5 (15)
C1—C2—C3—N1	−178.9 (7)	C9—C10—C11—C12	1.9 (16)
C3—N1—C4—C5	170.6 (8)	C10—C11—C12—C7	−1.6 (14)
C3—N1—C4—C6	−67.4 (10)	O1—C7—C12—C11	179.4 (7)
C1—O1—C7—C8	−2.6 (11)	C8—C7—C12—C11	0.9 (12)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···N1	0.82	2.31	2.760 (7)	115
N1—H1···O2ⁱ	0.90	1.84	2.742 (7)	179

Symmetry code: (i) −y+1, x, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₂H₁₉NO₂
M_r	209.28
Crystal system, space group	Tetragonal, P42₁c
Temperature (K)	298
a, c (Å)	15.1162 (17), 10.9448 (14)
V (Å³)	2500.9 (5)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.45 × 0.38 × 0.37

Data collection
Diffractometer	Bruker SMART CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.967, 0.973
No. of measured, independent and observed [I > 2σ(I)] reflections	9624, 1252, 676
R_int	0.125
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.064, 0.221, 1.16
No. of reflections	1252
No. of parameters	138
No. of restraints	16
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.24, −0.25

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008) and DIAMOND (Brandenburg, 1998), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···N1	0.82	2.31	2.760 (7)	115.1
N1—H1···O2ⁱ	0.90	1.84	2.742 (7)	179.0

Symmetry code: (i) −y+1, x, −z+1.

Acknowledgements

We gratefully acknowledge financial support from the National Natural Science Foundation of P. R. China (No. 20572103).

References

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