organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890

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

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[Ellison, K. E. & Gandhi, G. (2005). Drugs, pp. 787-797.]); Li et al. (2004[Li, Y., He, B., Qin, B., Feng, X. M. & Zhang, G. L. (2004). J. Org. Chem. pp. 7910-7913.]).

[Scheme 1]

Experimental

Crystal data
  • C12H20N2O

  • Mr = 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[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.965, Tmax = 0.971

  • 3608 measured reflections

  • 1449 independent reflections

  • 990 reflections with I > 2σ(I)

  • Rint = 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

  • Δρmax = 0.18 e Å−3

  • Δρmin = −0.13 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA 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[Siemens (1996). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Siemens, 1996[Siemens (1996). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information


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.

Refinement top

The amine and hydroxy H atoms were located in a difference Fourier map and refined freely. All other H atoms were placed geometrically and treated as riding on their parent atoms, with C—H = 0.93–0.96 Å and Uiso(H) = 1.2Ueq(C) or 1.5U eq(C) for methyl H atoms. In the absence of significant anomalous scattering, 464 Friedel pairs were merged.

Structure description 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.

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
[Figure 1] Fig. 1. The molecular structure of the compound, with atom labels and 50% probability displacement ellipsoids.
[Figure 2] 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
C12H20N2OF(000) = 228
Mr = 208.30Dx = 1.133 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 1130 reflections
a = 8.7676 (8) Åθ = 3.4–22.5°
b = 6.4662 (6) ŵ = 0.07 mm1
c = 11.1677 (12) ÅT = 296 K
β = 105.290 (1)°Block, colourless
V = 610.72 (10) Å30.50 × 0.49 × 0.40 mm
Z = 2
Data collection top
Siemens SMART CCD area-detector
diffractometer
1449 independent reflections
Radiation source: fine-focus sealed tube990 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.049
phi and ω scansθmax = 27.0°, θmin = 1.9°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1011
Tmin = 0.965, Tmax = 0.971k = 84
3608 measured reflectionsl = 1314
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.046Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.116H 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 parametersΔρmax = 0.18 e Å3
1 restraintΔρmin = 0.13 e Å3
Crystal data top
C12H20N2OV = 610.72 (10) Å3
Mr = 208.30Z = 2
Monoclinic, P21Mo Kα radiation
a = 8.7676 (8) ŵ = 0.07 mm1
b = 6.4662 (6) ÅT = 296 K
c = 11.1677 (12) Å0.50 × 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)
Tmin = 0.965, Tmax = 0.971Rint = 0.049
3608 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0461 restraint
wR(F2) = 0.116H atoms treated by a mixture of independent and constrained refinement
S = 0.94Δρmax = 0.18 e Å3
1449 reflectionsΔρmin = 0.13 e Å3
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
xyzUiso*/Ueq
N10.0180 (3)0.3886 (4)0.30241 (18)0.0486 (6)
N20.2976 (3)0.1975 (4)0.5341 (2)0.0607 (7)
O10.00479 (19)0.0345 (3)0.4500 (2)0.0517 (5)
C10.1036 (3)0.2296 (5)0.3115 (2)0.0567 (8)
H1A0.19980.29450.30280.068*
H1B0.06860.13240.24370.068*
C20.1394 (3)0.1128 (4)0.4333 (2)0.0478 (7)
H20.18710.20730.50150.057*
C30.2559 (3)0.0607 (5)0.4288 (2)0.0571 (8)
H3A0.21150.14340.35540.069*
H3B0.35230.00160.41850.069*
C40.4017 (3)0.1471 (5)0.6467 (2)0.0531 (7)
C50.4858 (3)0.0390 (5)0.6669 (2)0.0568 (7)
H50.47460.13340.60230.068*
C60.5857 (3)0.0842 (6)0.7822 (3)0.0689 (9)
H60.63950.20960.79450.083*
C70.6063 (4)0.0521 (7)0.8776 (3)0.0781 (11)
H70.67330.01980.95480.094*
C80.5280 (4)0.2371 (8)0.8595 (3)0.0839 (11)
H80.54300.33110.92450.101*
C90.4260 (3)0.2863 (6)0.7449 (3)0.0683 (9)
H90.37390.41290.73390.082*
C100.0414 (3)0.5221 (5)0.1919 (2)0.0523 (7)
H100.06090.58470.19330.063*
C110.0983 (4)0.4051 (6)0.0701 (2)0.0785 (10)
H11A0.19400.33240.06910.118*
H11B0.01870.30800.06210.118*
H11C0.11790.50110.00210.118*
C120.1543 (4)0.6954 (5)0.1993 (3)0.0667 (9)
H12A0.25790.63940.19150.100*
H12B0.15830.79220.13340.100*
H12C0.11840.76450.27780.100*
H1O0.010 (4)0.007 (6)0.519 (4)0.076 (12)*
H1N0.107 (4)0.331 (5)0.299 (3)0.068 (10)*
H2N0.222 (4)0.286 (6)0.539 (3)0.075 (11)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0497 (13)0.0528 (15)0.0470 (11)0.0033 (12)0.0195 (10)0.0038 (11)
N20.0601 (15)0.0547 (17)0.0713 (16)0.0032 (14)0.0240 (13)0.0041 (14)
O10.0544 (10)0.0537 (11)0.0498 (11)0.0009 (10)0.0186 (8)0.0034 (10)
C10.0639 (16)0.057 (2)0.0563 (15)0.0040 (16)0.0289 (13)0.0024 (14)
C20.0505 (15)0.0513 (17)0.0448 (13)0.0020 (13)0.0184 (10)0.0016 (13)
C30.0598 (17)0.062 (2)0.0536 (15)0.0069 (15)0.0215 (12)0.0056 (14)
C40.0434 (14)0.058 (2)0.0618 (16)0.0088 (14)0.0213 (13)0.0101 (15)
C50.0485 (13)0.0629 (19)0.0636 (16)0.0053 (16)0.0226 (13)0.0152 (16)
C60.0469 (15)0.086 (3)0.0747 (19)0.0013 (17)0.0180 (14)0.005 (2)
C70.0604 (19)0.105 (3)0.0686 (19)0.004 (2)0.0158 (15)0.006 (2)
C80.073 (2)0.112 (3)0.069 (2)0.025 (2)0.0243 (17)0.037 (2)
C90.0603 (18)0.064 (2)0.088 (2)0.0063 (16)0.0320 (16)0.0212 (18)
C100.0546 (14)0.0559 (17)0.0490 (14)0.0103 (15)0.0181 (11)0.0042 (14)
C110.103 (2)0.084 (3)0.0494 (15)0.000 (2)0.0210 (15)0.0005 (17)
C120.0734 (19)0.065 (2)0.0615 (16)0.0042 (17)0.0174 (14)0.0097 (16)
Geometric parameters (Å, º) top
N1—C11.465 (3)C5—H50.9300
N1—C101.476 (3)C6—C71.358 (5)
N1—H1N0.85 (3)C6—H60.9300
N2—C41.384 (4)C7—C81.368 (6)
N2—C31.440 (4)C7—H70.9300
N2—H2N0.89 (3)C8—C91.390 (5)
O1—C21.419 (3)C8—H80.9300
O1—H1O0.79 (4)C9—H90.9300
C1—C21.514 (3)C10—C121.512 (4)
C1—H1A0.9700C10—C111.521 (4)
C1—H1B0.9700C10—H100.9800
C2—C31.527 (4)C11—H11A0.9600
C2—H20.9800C11—H11B0.9600
C3—H3A0.9700C11—H11C0.9600
C3—H3B0.9700C12—H12A0.9600
C4—C91.391 (4)C12—H12B0.9600
C4—C51.399 (4)C12—H12C0.9600
C5—C61.384 (4)
C1—N1—C10114.0 (2)C7—C6—C5120.9 (3)
C1—N1—H1N110 (2)C7—C6—H6119.5
C10—N1—H1N107 (2)C5—C6—H6119.5
C4—N2—C3124.2 (3)C6—C7—C8119.6 (3)
C4—N2—H2N115.0 (19)C6—C7—H7120.2
C3—N2—H2N114 (2)C8—C7—H7120.2
C2—O1—H1O109 (2)C7—C8—C9120.8 (3)
N1—C1—C2112.8 (2)C7—C8—H8119.6
N1—C1—H1A109.0C9—C8—H8119.6
C2—C1—H1A109.0C8—C9—C4120.3 (3)
N1—C1—H1B109.0C8—C9—H9119.8
C2—C1—H1B109.0C4—C9—H9119.8
H1A—C1—H1B107.8N1—C10—C12109.6 (2)
O1—C2—C1108.4 (2)N1—C10—C11113.4 (3)
O1—C2—C3111.7 (2)C12—C10—C11110.7 (2)
C1—C2—C3108.6 (2)N1—C10—H10107.6
O1—C2—H2109.4C12—C10—H10107.6
C1—C2—H2109.4C11—C10—H10107.6
C3—C2—H2109.4C10—C11—H11A109.5
N2—C3—C2116.9 (2)C10—C11—H11B109.5
N2—C3—H3A108.1H11A—C11—H11B109.5
C2—C3—H3A108.1C10—C11—H11C109.5
N2—C3—H3B108.1H11A—C11—H11C109.5
C2—C3—H3B108.1H11B—C11—H11C109.5
H3A—C3—H3B107.3C10—C12—H12A109.5
N2—C4—C9119.4 (3)C10—C12—H12B109.5
N2—C4—C5122.9 (3)H12A—C12—H12B109.5
C9—C4—C5117.7 (3)C10—C12—H12C109.5
C6—C5—C4120.6 (3)H12A—C12—H12C109.5
C6—C5—H5119.7H12B—C12—H12C109.5
C4—C5—H5119.7
C10—N1—C1—C2172.8 (2)C9—C4—C5—C62.0 (4)
N1—C1—C2—O153.6 (3)C4—C5—C6—C71.1 (4)
N1—C1—C2—C3175.0 (2)C5—C6—C7—C80.4 (5)
C4—N2—C3—C276.6 (3)C6—C7—C8—C90.8 (5)
O1—C2—C3—N257.1 (3)C7—C8—C9—C40.2 (5)
C1—C2—C3—N2176.5 (3)N2—C4—C9—C8178.9 (3)
C3—N2—C4—C9176.0 (2)C5—C4—C9—C81.6 (4)
C3—N2—C4—C54.5 (4)C1—N1—C10—C12173.3 (2)
N2—C4—C5—C6178.5 (2)C1—N1—C10—C1162.5 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1O···N1i0.79 (4)2.09 (4)2.878 (3)173 (3)
N2—H2N···O1i0.89 (3)2.26 (3)3.141 (3)170 (3)
Symmetry code: (i) x, y1/2, z+1.

Experimental details

Crystal data
Chemical formulaC12H20N2O
Mr208.30
Crystal system, space groupMonoclinic, P21
Temperature (K)296
a, b, c (Å)8.7676 (8), 6.4662 (6), 11.1677 (12)
β (°) 105.290 (1)
V3)610.72 (10)
Z2
Radiation typeMo Kα
µ (mm1)0.07
Crystal size (mm)0.50 × 0.49 × 0.40
Data collection
DiffractometerSiemens SMART CCD area-detector
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.965, 0.971
No. of measured, independent and
observed [I > 2σ(I)] reflections
3608, 1449, 990
Rint0.049
(sin θ/λ)max1)0.639
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.046, 0.116, 0.94
No. of reflections1449
No. of parameters150
No. of restraints1
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)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···AD—HH···AD···AD—H···A
O1—H1O···N1i0.79 (4)2.09 (4)2.878 (3)173 (3)
N2—H2N···O1i0.89 (3)2.26 (3)3.141 (3)170 (3)
Symmetry code: (i) x, y1/2, z+1.
 

Acknowledgements

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

References

First citationEllison, K. E. & Gandhi, G. (2005). Drugs, pp. 787–797.  Web of Science CrossRef Google Scholar
First citationLi, Y., He, B., Qin, B., Feng, X. M. & Zhang, G. L. (2004). J. Org. Chem. pp. 7910–7913.  Web of Science CrossRef Google Scholar
First citationSheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSiemens (1996). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.  Google Scholar

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ISSN: 2056-9890
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