1-(Isopropyl-amino)-3-phen-oxy-propan-2-ol.

In the crystal structure of the title amino alcohol derivitive, C(12)H(19)NO(2), mol-ecules are linked by N-H⋯O hydrogen bonds. The mol-ecular structure exhibits an intra-molecular 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 = 209.28

Tetragonal,

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[F 2 > 2σ(F 2)] = 0.064

wR(F 2) = 0.221

S = 1.16

1252 reflections

138 parameters

16 restraints

H-atom parameters constrained

Δρmax = 0.24 e Å−3

Δρmin = −0.25 e Å−3

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.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812000566/lx2213sup1.cif

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

Supplementary material file. DOI: 10.1107/S1600536812000566/lx2213Isup3.cml

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

C12H19NO2	Dx = 1.112 Mg m−3
Mr = 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

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

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(Fo2) + (0.0662P)2 + 2.183P] where P = (Fo2 + 2Fc2)/3
1252 reflections	(Δ/σ)max < 0.001
138 parameters	Δρmax = 0.24 e Å−3
16 restraints	Δρmin = −0.25 e Å−3

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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

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) .