3-Anilino-1-(isopropyl­amino)­propan-2-ol

Hou, X.; Hu, P.; Lv, Q.

doi:10.1107/S1600536812013256

organic compounds

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ISSN: 2056-9890

Volume 68| Part 4| April 2012| Page o1264

doi:10.1107/S1600536812013256

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3-Anilino-1-(isopropylamino)propan-2-ol

Xuehui Hou,^a Ping Hu ^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 5 March 2012; accepted 27 March 2012; online 31 March 2012)

The title compound, C₁₂H₂₀N₂O, was obtained by the reaction of N-(oxiran-2-ylmethyl)aniline and propan-2-amine. In the crystal, molecules 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_r = 208.30
Monoclinic, P 2₁
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[F² > 2σ(F²)] = 0.046
wR(F²) = 0.116
S = 0.94
1449 reflections
150 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.13 e Å⁻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) $[-x, y-{\script{1\over 2}}, -z+1]$ .

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); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812013256/rz2719sup1.cif

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

Supporting information file. DOI: 10.1107/S1600536812013256/rz2719Isup3.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 & Gandhi, 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 field, we report here the crystal structure of the title compound.

The molecular structure of the title compound is shown in Fig. 1. A l l bond lengths and angles are not unexceptional. In the crystal structure (Fig. 2), intermolecular O—H···N and N—H···O hydrogen bonds (Table 1) link molecules into chains running parallel to the b axis.

Related literature top

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

Experimental top

To a solution of N-(oxiran-2-ylmethyl)aniline (14.9 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, then it was concentrated under reduced pressure and purified by crystallization from ethyl acetate, giving colourless single crystals of the title compound suitablu for X-ray analysis.

Structure description top

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

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); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the compound, with atom labels and 50% probability displacement ellipsoids.
	Fig. 2. Crystal packing of the title compound viewed along the b axis, showing the molecular chains formed by intermolecular hydrogen bonds (dashed lines).

3-Anilino-1-(isopropylamino)propan-2-ol top

Crystal data top

C₁₂H₂₀N₂O	F(000) = 228
M_r = 208.30	D_x = 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

Data collection top

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

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)] = 0.046	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(F_o²) + (0.0624P)²] where P = (F_o² + 2F_c²)/3
1449 reflections	(Δ/σ)_max < 0.001
150 parameters	Δρ_max = 0.18 e Å⁻³
1 restraint	Δρ_min = −0.13 e Å⁻³

Crystal data top

C₁₂H₂₀N₂O	V = 610.72 (10) Å³
M_r = 208.30	Z = 2
Monoclinic, P2₁	Mo Kα radiation
a = 8.7676 (8) Å	µ = 0.07 mm⁻¹
b = 6.4662 (6) Å	T = 296 K
c = 11.1677 (12) Å	0.50 × 0.49 × 0.40 mm
β = 105.290 (1)°

Data collection top

Siemens SMART CCD area-detector diffractometer	1449 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	990 reflections with I > 2σ(I)
T_min = 0.965, T_max = 0.971	R_int = 0.049
3608 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	1 restraint
wR(F²) = 0.116	H atoms treated by a mixture of independent and constrained refinement
S = 0.94	Δρ_max = 0.18 e Å⁻³
1449 reflections	Δρ_min = −0.13 e Å⁻³
150 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
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)*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x, y−1/2, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₂H₂₀N₂O
M_r	208.30
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	296
a, b, c (Å)	8.7676 (8), 6.4662 (6), 11.1677 (12)
β (°)	105.290 (1)
V (Å³)	610.72 (10)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.07
Crystal size (mm)	0.50 × 0.49 × 0.40

Data collection
Diffractometer	Siemens SMART CCD area-detector
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.965, 0.971
No. of measured, independent and observed [I > 2σ(I)] reflections	3608, 1449, 990
R_int	0.049
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.116, 0.94
No. of reflections	1449
No. of parameters	150
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)	0.18, −0.13

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

Hydrogen-bond geometry (Å, º) top

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) −x, y−1/2, −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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