3-Anilino-1-(isopropyl-amino)-propan-2-ol.

The title compound, C(12)H(20)N(2)O, was obtained by the reaction of N-(oxiran-2-ylmeth-yl)aniline and propan-2-amine. In the crystal, mol-ecules are linked by O-H⋯N and N-H⋯O hydrogen bonds into chains parallel to the b axis.

Related literature

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

Experimental

Crystal data

C12H20N2O

M = 208.30

Monoclinic,

a = 8.7676 (8) Å

b = 6.4662 (6) Å

c = 11.1677 (12) Å

β = 105.290 (1)°

V = 610.72 (10) Å3

Z = 2

Mo Kα radiation

μ = 0.07 mm−1

T = 296 K

0.50 × 0.49 × 0.40 mm

Data collection

Siemens SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.965, T max = 0.971

3608 measured reflections

1449 independent reflections

990 reflections with I > 2σ(I)

R int = 0.049

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.116

S = 0.94

1449 reflections

150 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.18 e Å−3

Δρmin = −0.13 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 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812013256/rz2719sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812013256/rz2719Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812013256/rz2719Isup3.cml

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

C12H20N2O	F(000) = 228
Mr = 208.30	Dx = 1.133 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 1130 reflections
a = 8.7676 (8) Å	θ = 3.4–22.5°
b = 6.4662 (6) Å	µ = 0.07 mm−1
c = 11.1677 (12) Å	T = 296 K
β = 105.290 (1)°	Block, colourless
V = 610.72 (10) Å3	0.50 × 0.49 × 0.40 mm
Z = 2

Siemens SMART CCD area-detector diffractometer	1449 independent reflections
Radiation source: fine-focus sealed tube	990 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.049
phi and ω scans	θmax = 27.0°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→11
Tmin = 0.965, Tmax = 0.971	k = −8→4
3608 measured reflections	l = −13→14

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.116	H atoms treated by a mixture of independent and constrained refinement
S = 0.94	w = 1/[σ2(Fo2) + (0.0624P)2] where P = (Fo2 + 2Fc2)/3
1449 reflections	(Δ/σ)max < 0.001
150 parameters	Δρmax = 0.18 e Å−3
1 restraint	Δρmin = −0.13 e Å−3

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
N1	−0.0180 (3)	0.3886 (4)	0.30241 (18)	0.0486 (6)
N2	0.2976 (3)	−0.1975 (4)	0.5341 (2)	0.0607 (7)
O1	−0.00479 (19)	0.0345 (3)	0.4500 (2)	0.0517 (5)
C1	0.1036 (3)	0.2296 (5)	0.3115 (2)	0.0567 (8)
H1A	0.1998	0.2945	0.3028	0.068*
H1B	0.0686	0.1324	0.2437	0.068*
C2	0.1394 (3)	0.1128 (4)	0.4333 (2)	0.0478 (7)
H2	0.1871	0.2073	0.5015	0.057*
C3	0.2559 (3)	−0.0607 (5)	0.4288 (2)	0.0571 (8)
H3A	0.2115	−0.1434	0.3554	0.069*
H3B	0.3523	0.0016	0.4185	0.069*
C4	0.4017 (3)	−0.1471 (5)	0.6467 (2)	0.0531 (7)
C5	0.4858 (3)	0.0390 (5)	0.6669 (2)	0.0568 (7)
H5	0.4746	0.1334	0.6023	0.068*
C6	0.5857 (3)	0.0842 (6)	0.7822 (3)	0.0689 (9)
H6	0.6395	0.2096	0.7945	0.083*
C7	0.6063 (4)	−0.0521 (7)	0.8776 (3)	0.0781 (11)
H7	0.6733	−0.0198	0.9548	0.094*
C8	0.5280 (4)	−0.2371 (8)	0.8595 (3)	0.0839 (11)
H8	0.5430	−0.3311	0.9245	0.101*
C9	0.4260 (3)	−0.2863 (6)	0.7449 (3)	0.0683 (9)
H9	0.3739	−0.4129	0.7339	0.082*
C10	−0.0414 (3)	0.5221 (5)	0.1919 (2)	0.0523 (7)
H10	0.0609	0.5847	0.1933	0.063*
C11	−0.0983 (4)	0.4051 (6)	0.0701 (2)	0.0785 (10)
H11A	−0.1940	0.3324	0.0691	0.118*
H11B	−0.0187	0.3080	0.0621	0.118*
H11C	−0.1179	0.5011	0.0021	0.118*
C12	−0.1543 (4)	0.6954 (5)	0.1993 (3)	0.0667 (9)
H12A	−0.2579	0.6394	0.1915	0.100*
H12B	−0.1583	0.7922	0.1334	0.100*
H12C	−0.1184	0.7645	0.2778	0.100*
H1O	0.010 (4)	−0.007 (6)	0.519 (4)	0.076 (12)*
H1N	−0.107 (4)	0.331 (5)	0.299 (3)	0.068 (10)*
H2N	0.222 (4)	−0.286 (6)	0.539 (3)	0.075 (11)*

	U11	U22	U33	U12	U13	U23
N1	0.0497 (13)	0.0528 (15)	0.0470 (11)	−0.0033 (12)	0.0195 (10)	0.0038 (11)
N2	0.0601 (15)	0.0547 (17)	0.0713 (16)	0.0032 (14)	0.0240 (13)	0.0041 (14)
O1	0.0544 (10)	0.0537 (11)	0.0498 (11)	−0.0009 (10)	0.0186 (8)	0.0034 (10)
C1	0.0639 (16)	0.057 (2)	0.0563 (15)	0.0040 (16)	0.0289 (13)	0.0024 (14)
C2	0.0505 (15)	0.0513 (17)	0.0448 (13)	0.0020 (13)	0.0184 (10)	−0.0016 (13)
C3	0.0598 (17)	0.062 (2)	0.0536 (15)	0.0069 (15)	0.0215 (12)	−0.0056 (14)
C4	0.0434 (14)	0.058 (2)	0.0618 (16)	0.0088 (14)	0.0213 (13)	0.0101 (15)
C5	0.0485 (13)	0.0629 (19)	0.0636 (16)	0.0053 (16)	0.0226 (13)	0.0152 (16)
C6	0.0469 (15)	0.086 (3)	0.0747 (19)	0.0013 (17)	0.0180 (14)	0.005 (2)
C7	0.0604 (19)	0.105 (3)	0.0686 (19)	0.004 (2)	0.0158 (15)	0.006 (2)
C8	0.073 (2)	0.112 (3)	0.069 (2)	0.025 (2)	0.0243 (17)	0.037 (2)
C9	0.0603 (18)	0.064 (2)	0.088 (2)	0.0063 (16)	0.0320 (16)	0.0212 (18)
C10	0.0546 (14)	0.0559 (17)	0.0490 (14)	−0.0103 (15)	0.0181 (11)	0.0042 (14)
C11	0.103 (2)	0.084 (3)	0.0494 (15)	0.000 (2)	0.0210 (15)	0.0005 (17)
C12	0.0734 (19)	0.065 (2)	0.0615 (16)	0.0042 (17)	0.0174 (14)	0.0097 (16)

N1—C1	1.465 (3)	C5—H5	0.9300
N1—C10	1.476 (3)	C6—C7	1.358 (5)
N1—H1N	0.85 (3)	C6—H6	0.9300
N2—C4	1.384 (4)	C7—C8	1.368 (6)
N2—C3	1.440 (4)	C7—H7	0.9300
N2—H2N	0.89 (3)	C8—C9	1.390 (5)
O1—C2	1.419 (3)	C8—H8	0.9300
O1—H1O	0.79 (4)	C9—H9	0.9300
C1—C2	1.514 (3)	C10—C12	1.512 (4)
C1—H1A	0.9700	C10—C11	1.521 (4)
C1—H1B	0.9700	C10—H10	0.9800
C2—C3	1.527 (4)	C11—H11A	0.9600
C2—H2	0.9800	C11—H11B	0.9600
C3—H3A	0.9700	C11—H11C	0.9600
C3—H3B	0.9700	C12—H12A	0.9600
C4—C9	1.391 (4)	C12—H12B	0.9600
C4—C5	1.399 (4)	C12—H12C	0.9600
C5—C6	1.384 (4)
C1—N1—C10	114.0 (2)	C7—C6—C5	120.9 (3)
C1—N1—H1N	110 (2)	C7—C6—H6	119.5
C10—N1—H1N	107 (2)	C5—C6—H6	119.5
C4—N2—C3	124.2 (3)	C6—C7—C8	119.6 (3)
C4—N2—H2N	115.0 (19)	C6—C7—H7	120.2
C3—N2—H2N	114 (2)	C8—C7—H7	120.2
C2—O1—H1O	109 (2)	C7—C8—C9	120.8 (3)
N1—C1—C2	112.8 (2)	C7—C8—H8	119.6
N1—C1—H1A	109.0	C9—C8—H8	119.6
C2—C1—H1A	109.0	C8—C9—C4	120.3 (3)
N1—C1—H1B	109.0	C8—C9—H9	119.8
C2—C1—H1B	109.0	C4—C9—H9	119.8
H1A—C1—H1B	107.8	N1—C10—C12	109.6 (2)
O1—C2—C1	108.4 (2)	N1—C10—C11	113.4 (3)
O1—C2—C3	111.7 (2)	C12—C10—C11	110.7 (2)
C1—C2—C3	108.6 (2)	N1—C10—H10	107.6
O1—C2—H2	109.4	C12—C10—H10	107.6
C1—C2—H2	109.4	C11—C10—H10	107.6
C3—C2—H2	109.4	C10—C11—H11A	109.5
N2—C3—C2	116.9 (2)	C10—C11—H11B	109.5
N2—C3—H3A	108.1	H11A—C11—H11B	109.5
C2—C3—H3A	108.1	C10—C11—H11C	109.5
N2—C3—H3B	108.1	H11A—C11—H11C	109.5
C2—C3—H3B	108.1	H11B—C11—H11C	109.5
H3A—C3—H3B	107.3	C10—C12—H12A	109.5
N2—C4—C9	119.4 (3)	C10—C12—H12B	109.5
N2—C4—C5	122.9 (3)	H12A—C12—H12B	109.5
C9—C4—C5	117.7 (3)	C10—C12—H12C	109.5
C6—C5—C4	120.6 (3)	H12A—C12—H12C	109.5
C6—C5—H5	119.7	H12B—C12—H12C	109.5
C4—C5—H5	119.7
C10—N1—C1—C2	172.8 (2)	C9—C4—C5—C6	−2.0 (4)
N1—C1—C2—O1	53.6 (3)	C4—C5—C6—C7	1.1 (4)
N1—C1—C2—C3	175.0 (2)	C5—C6—C7—C8	0.4 (5)
C4—N2—C3—C2	−76.6 (3)	C6—C7—C8—C9	−0.8 (5)
O1—C2—C3—N2	−57.1 (3)	C7—C8—C9—C4	−0.2 (5)
C1—C2—C3—N2	−176.5 (3)	N2—C4—C9—C8	−178.9 (3)
C3—N2—C4—C9	176.0 (2)	C5—C4—C9—C8	1.6 (4)
C3—N2—C4—C5	−4.5 (4)	C1—N1—C10—C12	−173.3 (2)
N2—C4—C5—C6	178.5 (2)	C1—N1—C10—C11	62.5 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O···N1i	0.79 (4)	2.09 (4)	2.878 (3)	173 (3)
N2—H2N···O1i	0.89 (3)	2.26 (3)	3.141 (3)	170 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1O⋯N1i	0.79 (4)	2.09 (4)	2.878 (3)	173 (3)
N2—H2N⋯O1i	0.89 (3)	2.26 (3)	3.141 (3)	170 (3)

Symmetry code: (i) .