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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 65| Part 1| January 2009| Page o206
doi:10.1107/S1600536808043183

3-[(3-Hydroxypropyl)amino]-1-phenyl­but-2-en-1-one

T. S. Arul Jeevana* and K. S. Nagarajaa

aDepartment of Chemistry, Loyola Institute of Frontier Energy, Loyola College, Chennai 600 034, India
*Correspondence e-mail: jejeevan@gmail.com

(Received 1 December 2008; accepted 18 December 2008; online 24 December 2008)

The title compound, C13H17NO2, has an intra­molecular N—H⋯O hydrogen bond, forming a planar six-membered ring with a mean deviation of 0.015 (5) Å from the plane. This plane makes a dihedral angle of 7.19 (8)° with the adjacent phenyl ring. Through an inter­molecular O—H⋯O hydrogen bond, the mol­ecules with their 21 screw and b-translation equivalents form a helical chain running parallel to the b axis.

Related literature

For general background, see: Morozova et al. (2007[Morozova, N. B., Stabnikov, P. A. & Igumenov, I. K. (2007). J. Struct. Chem. 48, 889-898.]). For a related structure, see: Shi (2005[Shi, Y.-C. (2005). Acta Cryst. E61, o2005-o2007.]).

[Scheme 1]

Experimental

Crystal data

  • C13H17NO2

  • Mr = 219.28

  • Orthorhombic, P 21 21 21

  • a = 5.9131 (3) Å

  • b = 8.0101 (4) Å

  • c = 24.9626 (13) Å

  • V = 1182.34 (10) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.08 mm−1

  • T = 293 (2) K

  • 0.30 × 0.20 × 0.20 mm
Data collection

  • Bruker Kappa APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 1999[Bruker (1999). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.944, Tmax = 0.984

  • 11541 measured reflections

  • 1236 independent reflections

  • 1168 reflections with I > 2σ(I)

  • Rint = 0.022
Refinement

  • R[F2 > 2σ(F2)] = 0.028

  • wR(F2) = 0.079

  • S = 1.05

  • 1236 reflections

  • 153 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.12 e Å−3

  • Δρmin = −0.09 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
O2—H2A⋯O1i 0.82 1.99 2.805 (2) 176
N1—H1N⋯O1 0.85 (2) 1.94 (2) 2.642 (2) 139.1 (18)
Symmetry code: (i) [-x, y+{\script{1\over 2}}, -z+{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2004[Bruker (2004). APEX2 and SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT-Plus (Bruker, 2004[Bruker (2004). APEX2 and SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT-Plus; program(s) used to solve structure: SIR92 (Altomare et al., 1994[Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]) and Mercury (Macrae et al., 2006[Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.]); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808043183/is2371sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808043183/is2371Isup2.hkl

checkCIF report


Comment top

The Schiff base 1-phenyl-3-[(3-hydroxypropyl)amino]-1-butanone could be a good chelating ligand and may find use in the field of coordination chemistry of transition metal complexes. The compound could act as a bidentate ligand through the N and O atoms. The replacement of oxygen by nitrogen in the ligand can increase the covalency of the complexes (Morozova et al., 2007).

Figure 1 gives ORTEP representation of the molecule with atoms represented as 50% anisotropic ellipsoids. Figure 2 gives packing of the molecules showing hydrogen bonded interactions. The molecules and their 21 screw translation equivalents are bound through O2—H2A···O1 hydrogen bonds (Table 1). These H-bonded pairs are further linked with their b-translation equivalents to form an one-dimensional hydrogen bonded network parallel to b axis. There is an intramolecular N1—H1···O1 hydrogen bond between the imino hydrogen and the keto oxygen (Table 1). The packing is further stabilized through van der Waals interactions. The crystal is found to cleave easily through the (001) plane. The closely related compound, C12H15O2N, (3-[(2-hydroxyethyl)amino]-1-phenylbut-2-en-1-one) crystallizes in monoclinic system with centrosymmetric space group P21/n, forming hydrogen bonded dimers in the structure (Shi, 2005), while the title compound crystallizes in polar space group P212121 and with extended hydrogen bonding in the structure.

Related literature top

For general background, see: Morozova et al. (2007). For a related structure, see: Shi (2005).

Experimental top

The title Schiff base ligand was synthesized by the condensation of 3-amino-1-propanol and benzoylacetone. To 0.1 molar solution of 3-amino-1-propanol (dissolved in 5 ml of ethanol) was slowly added to a 0.1 molar solution (in ethanol) of benzoylacetone. The reaction mixture was refluxed for 30 min. The solution was cooled overnight and the precipitate was washed with ethanol. The compound was crystallized in ethanol by slow evaporation (m.p. = 394 K). Anal. Calc. for C13H18O2N: (Found %): C 70.88 (69.96), H 8.24 (8.13), N 6.35 (6.26). IR (KBr, cm-1): 3170 = v(O—H); 3340, v(N—H); 1596, v[(C—N)—C=C)]; 1265, v(C—O). 1H NMR (400 MHz, CDCl3) δ values at 1.8, 2.0, 3.4, 3.6, 5.7 and 7.4 p.p.m. for CH3, CH2, NH—CH2, CH2—OH, H—C=C and aromatic protons respectively. 13C NMR (400 MHz, CDCl3) δ values at 14.83, 32.53, 40.06, 92.46, 128, 140.39 and 187 for CH3, CH2,-HN—CH2, –CH2OH, Aromatic, C—CH=C– and C=O carbon respectively. Mass Spectra: M+, m/z = 220.29, (I = 19%); M [L-(O—CH2—CH2—CH2—N)]+, 148.10, (22); M [(C6H5-C=O)]+, 104.52, (100); M [(O—CH2—CH2—CH2—N)]+, 74.63, (65).

Refinement top

All the hydrogen atoms could be located in a difference Fourier map. However, the H atoms except that of NH, were fixed at geometrically meaningful positions and refined using riding model. The riding tertiary CH3 hydrogen atoms were assigned 1.5 times the equivalent displacement parameters of parent atoms, while 1.2 times was assigned for CH2 and aromatic H atoms. The aromatic C—H distances were fixed at 0.93 Å while the secondary CH2 and tertiary CH3 were assigned 0.97 Å and 0.96 Å respectively. The isotropic displacement parameter of hydroxyl hydrogen was refined. In the absence of significant anomalous scattering effects, Friedel pairs have been merged.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2 (Bruker, 2004); data reduction: SAINT-Plus (Bruker, 2004); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2006); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The ORTEP representation of the molecule with atoms represented as 50% probability ellipsoid.
[Figure 2] Fig. 2. Packing of molecules in the unit cell. Intra and intermolecular interactions are shown with dotted lines.
3-[(3-Hydroxypropyl)amino]-1-phenylbut-2-en-1-one top
Crystal data top
C13H17NO2F(000) = 472
Mr = 219.28Dx = 1.232 Mg m−3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 7505 reflections
a = 5.9131 (3) Åθ = 2.5–31.0°
b = 8.0101 (4) ŵ = 0.08 mm−1
c = 24.9626 (13) ÅT = 293 K
V = 1182.34 (10) Å3Needle, colourless
Z = 40.30 × 0.20 × 0.20 mm
Data collection top
Bruker Kappa APEXII CCD
diffractometer		1236 independent reflections
Radiation source: fine-focus sealed tube1168 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.022
ω and ϕ scanθmax = 25.0°, θmin = 2.7°
Absorption correction: multi-scan
(SADABS; Bruker, 1999)		h = −7→5
Tmin = 0.944, Tmax = 0.984k = −9→9
11541 measured reflectionsl = −29→28
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.028H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.079 w = 1/[σ2(Fo2) + (0.0436P)2 + 0.1578P]
where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max < 0.001
1236 reflectionsΔρmax = 0.12 e Å−3
153 parametersΔρmin = −0.09 e Å−3
0 restraintsExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.025 (3)
Crystal data top
C13H17NO2V = 1182.34 (10) Å3
Mr = 219.28Z = 4
Orthorhombic, P212121Mo Kα radiation
a = 5.9131 (3) ŵ = 0.08 mm−1
b = 8.0101 (4) ÅT = 293 K
c = 24.9626 (13) Å0.30 × 0.20 × 0.20 mm
Data collection top
Bruker Kappa APEXII CCD
diffractometer		1236 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 1999)		1168 reflections with I > 2σ(I)
Tmin = 0.944, Tmax = 0.984Rint = 0.022
11541 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0280 restraints
wR(F2) = 0.079H atoms treated by a mixture of independent and constrained refinement
S = 1.05Δρmax = 0.12 e Å−3
1236 reflectionsΔρmin = −0.09 e Å−3
153 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
C10.5484 (4)−0.3200 (2)0.04625 (8)0.0547 (5)
H10.6664−0.24390.04300.066*
C20.5575 (4)−0.4692 (3)0.01828 (8)0.0652 (6)
H20.6805−0.4922−0.00370.078*
C30.3864 (4)−0.5822 (3)0.02298 (8)0.0647 (6)
H30.3928−0.68250.00430.078*
C40.2058 (4)−0.5480 (3)0.05513 (8)0.0664 (6)
H40.0900−0.62580.05860.080*
C50.1939 (4)−0.3984 (3)0.08253 (7)0.0554 (5)
H50.0680−0.37530.10360.066*
C60.3664 (3)−0.2826 (2)0.07901 (6)0.0410 (4)
C70.3439 (3)−0.1211 (2)0.10934 (6)0.0400 (4)
C80.5240 (3)−0.0080 (2)0.11068 (6)0.0428 (4)
H80.6541−0.03420.09150.048 (5)*
C90.5197 (3)0.1415 (2)0.13909 (6)0.0409 (4)
C100.7269 (3)0.2485 (3)0.14091 (9)0.0608 (5)
H9A0.69290.35660.12640.091*
H9B0.84470.19730.12010.091*
H9C0.77620.26010.17740.091*
C110.3128 (3)0.3395 (2)0.19816 (7)0.0489 (5)
H10A0.16090.38290.19360.059*
H10B0.41800.42380.18570.059*
C120.3543 (3)0.3077 (3)0.25711 (7)0.0560 (5)
H11A0.50890.26990.26180.067*
H11B0.33770.41200.27650.067*
C130.1971 (4)0.1805 (3)0.28110 (7)0.0575 (5)
H12A0.22230.07350.26390.069*
H12B0.23180.16790.31890.069*
N10.3385 (3)0.19014 (19)0.16559 (6)0.0438 (4)
O10.1589 (2)−0.09436 (16)0.13305 (5)0.0543 (4)
O2−0.0328 (2)0.2249 (2)0.27548 (6)0.0679 (4)
H2A−0.07230.28080.30140.099 (10)*
H1N0.227 (3)0.124 (3)0.1625 (8)0.049 (5)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0546 (11)0.0488 (10)0.0607 (10)−0.0008 (10)0.0154 (9)0.0000 (9)
C20.0728 (14)0.0592 (12)0.0638 (12)0.0068 (12)0.0237 (12)−0.0057 (10)
C30.0883 (16)0.0500 (11)0.0559 (10)−0.0010 (12)0.0091 (12)−0.0107 (9)
C40.0767 (16)0.0610 (12)0.0615 (11)−0.0212 (12)0.0108 (12)−0.0123 (10)
C50.0540 (11)0.0626 (11)0.0495 (9)−0.0137 (11)0.0107 (9)−0.0108 (9)
C60.0435 (9)0.0453 (9)0.0341 (7)−0.0013 (8)0.0018 (7)0.0036 (7)
C70.0389 (9)0.0474 (9)0.0338 (7)−0.0013 (8)0.0041 (7)0.0029 (7)
C80.0386 (9)0.0511 (10)0.0388 (8)−0.0040 (8)0.0076 (8)−0.0018 (7)
C90.0359 (9)0.0509 (9)0.0359 (7)−0.0064 (8)0.0011 (7)0.0042 (7)
C100.0451 (11)0.0699 (13)0.0674 (11)−0.0171 (10)0.0066 (9)−0.0082 (11)
C110.0467 (10)0.0418 (9)0.0583 (9)−0.0049 (9)0.0044 (9)−0.0059 (8)
C120.0481 (10)0.0662 (12)0.0538 (9)0.0008 (11)−0.0027 (9)−0.0156 (9)
C130.0636 (13)0.0598 (12)0.0492 (9)0.0125 (12)0.0086 (9)−0.0018 (9)
N10.0384 (8)0.0449 (8)0.0481 (7)−0.0081 (8)0.0042 (7)−0.0052 (7)
O10.0418 (7)0.0553 (7)0.0659 (7)−0.0085 (7)0.0168 (6)−0.0116 (6)
O20.0542 (9)0.0851 (11)0.0643 (8)−0.0029 (9)0.0093 (7)−0.0059 (9)
Geometric parameters (Å, º) top
C1—C61.385 (3)C9—C101.496 (2)
C1—C21.385 (3)C10—H9A0.9600
C1—H10.9300C10—H9B0.9600
C2—C31.363 (3)C10—H9C0.9600
C2—H20.9300C11—N11.454 (2)
C3—C41.364 (3)C11—C121.513 (2)
C3—H30.9300C11—H10A0.9700
C4—C51.382 (3)C11—H10B0.9700
C4—H40.9300C12—C131.504 (3)
C5—C61.381 (3)C12—H11A0.9700
C5—H50.9300C12—H11B0.9700
C6—C71.505 (2)C13—O21.412 (3)
C7—O11.262 (2)C13—H12A0.9700
C7—C81.399 (2)C13—H12B0.9700
C8—C91.392 (2)N1—H1N0.85 (2)
C8—H80.9300O2—H2A0.8200
C9—N11.318 (2)
C6—C1—C2120.95 (19)C9—C10—H9B109.5
C6—C1—H1119.5H9A—C10—H9B109.5
C2—C1—H1119.5C9—C10—H9C109.5
C3—C2—C1120.07 (19)H9A—C10—H9C109.5
C3—C2—H2120.0H9B—C10—H9C109.5
C1—C2—H2120.0N1—C11—C12112.86 (16)
C2—C3—C4119.90 (19)N1—C11—H10A109.0
C2—C3—H3120.0C12—C11—H10A109.0
C4—C3—H3120.0N1—C11—H10B109.0
C3—C4—C5120.4 (2)C12—C11—H10B109.0
C3—C4—H4119.8H10A—C11—H10B107.8
C5—C4—H4119.8C13—C12—C11113.63 (16)
C6—C5—C4120.85 (18)C13—C12—H11A108.8
C6—C5—H5119.6C11—C12—H11A108.8
C4—C5—H5119.6C13—C12—H11B108.8
C5—C6—C1117.82 (16)C11—C12—H11B108.8
C5—C6—C7118.66 (15)H11A—C12—H11B107.7
C1—C6—C7123.48 (16)O2—C13—C12112.62 (18)
O1—C7—C8122.59 (15)O2—C13—H12A109.1
O1—C7—C6117.30 (15)C12—C13—H12A109.1
C8—C7—C6120.12 (15)O2—C13—H12B109.1
C9—C8—C7123.76 (15)C12—C13—H12B109.1
C9—C8—H8118.1H12A—C13—H12B107.8
C7—C8—H8118.1C9—N1—C11127.51 (16)
N1—C9—C8121.66 (16)C9—N1—H1N113.8 (13)
N1—C9—C10118.77 (15)C11—N1—H1N118.7 (13)
C8—C9—C10119.55 (15)C13—O2—H2A109.5
C9—C10—H9A109.5
C6—C1—C2—C3−0.4 (3)C1—C6—C7—C8−7.9 (2)
C1—C2—C3—C40.2 (4)O1—C7—C8—C91.8 (3)
C2—C3—C4—C50.8 (4)C6—C7—C8—C9−177.97 (15)
C3—C4—C5—C6−1.6 (3)C7—C8—C9—N1−2.6 (2)
C4—C5—C6—C11.4 (3)C7—C8—C9—C10175.92 (16)
C4—C5—C6—C7179.54 (18)N1—C11—C12—C13−59.7 (2)
C2—C1—C6—C5−0.4 (3)C11—C12—C13—O2−57.9 (2)
C2—C1—C6—C7−178.45 (18)C8—C9—N1—C11177.83 (15)
C5—C6—C7—O1−5.7 (2)C10—C9—N1—C11−0.7 (3)
C1—C6—C7—O1172.33 (17)C12—C11—N1—C9−95.5 (2)
C5—C6—C7—C8174.08 (16)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2A···O1i0.821.992.805 (2)176
N1—H1N···O10.85 (2)1.94 (2)2.642 (2)139.1 (18)
Symmetry code: (i) −x, y+1/2, −z+1/2.

Experimental details

Crystal data
Chemical formulaC13H17NO2
Mr219.28
Crystal system, space groupOrthorhombic, P212121
Temperature (K)293
a, b, c (Å)5.9131 (3), 8.0101 (4), 24.9626 (13)
V (Å3)1182.34 (10)
Z4
Radiation typeMo Kα
µ (mm−1)0.08
Crystal size (mm)0.30 × 0.20 × 0.20
Data collection
DiffractometerBruker Kappa APEXII CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 1999)
Tmin, Tmax0.944, 0.984
No. of measured, independent and
observed [I > 2σ(I)] reflections		11541, 1236, 1168
Rint0.022
(sin θ/λ)max (Å−1)0.594
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.028, 0.079, 1.05
No. of reflections1236
No. of parameters153
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)0.12, −0.09

Computer programs: APEX2 (Bruker, 2004), SAINT-Plus (Bruker, 2004), SIR92 (Altomare et al., 1994), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2006).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2A···O1i0.821.992.805 (2)176.4
N1—H1N···O10.85 (2)1.94 (2)2.642 (2)139.1 (18)
Symmetry code: (i) −x, y+1/2, −z+1/2.
 

Acknowledgements

The authors express their thanks to the Sophisticated Analytical Instruments Facility, Indian Institute of Technology Madras, Chennai, for the collection of X-ray diffraction data. The authors are also grateful to the Department of Science and Technology (DST), India, for financial support (SR/S3/ME/03/2005-SERC) to carry out this work.

References

First citationAltomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435.  CrossRef Web of Science IUCr Journals Google Scholar
 First citationBruker (1999). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
 First citationBruker (2004). APEX2 and SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
 First citationFarrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  CrossRef IUCr Journals Google Scholar
 First citationMacrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453–457.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationMorozova, N. B., Stabnikov, P. A. & Igumenov, I. K. (2007). J. Struct. Chem. 48, 889–898.  Web of Science CrossRef CAS Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationShi, Y.-C. (2005). Acta Cryst. E61, o2005–o2007.  Web of Science CSD CrossRef IUCr Journals Google Scholar

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ISSN: 2056-9890
Volume 65| Part 1| January 2009| Page o206
doi:10.1107/S1600536808043183
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