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

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N,N′-(2-Hy­dr­oxy­propane-1,3-di­yl)bis­­(2-hy­dr­oxy­benzamide) monohydrate

aLaboratoire de Chimie Inorganiue et d'Environment, Université def Tlemcen, BP 119, Tlemcen, 13 000, Algeria, bUnité de Recherche de Chimie de l'Environnement et Moléculaire Structurale, CHEMS, Université Mentouri-Constantine, 25000 , Algeria, cLaboratoire d'Electrochimie, d'Ingénierie Moléculaire et de Catalyse Redox (LEIMCR), Faculté des Sciences de l'Ingénieur, Université Farhat Abbas, Sétif, 19000 , Algeria, and dCentre de Difractométrie X, UMR 6226 CNRS Unité Sciences Chimiques de Rennes, Université de Rennes I, 263 Avenue du Général Leclerc, 35042 Rennes, France
*Correspondence e-mail: bouacida_sofiane@yahoo.fr

(Received 17 September 2013; accepted 22 September 2013; online 28 September 2013)

In the title hydrate, C17H18N2O5·H2O, the complete organic mol­ecule is generated by a crystallographic mirror plane with one C and one O atom lying on the mirror plane. The O atom of the water mol­ecule has m site symmetry. Two symmetry-related intra­molecular O—H⋯O hydrogen bonds complete S(6) rings in the organic mol­ecule. In the crystal, the components are linked into (010) sheets by O—H⋯O and N—H⋯O hydrogen bonds.

Related literature

For the synthesis of similar compounds and their complexes see: Kumar & Debashis (2006[Kumar, P. N. & Debashis, R. (2006). J. Chem. Res. pp. 632-635.]); Azam et al. (2012[Azam, M., Zahid, H., Warad, I., Al-Resayes, S. I., Shahnawaz Khan, M., Shakir, M., Trzesowska-Kruszynska, A. & Kruszynski, R. (2012). Dalton Trans. 41, 10854-10864.]); Sarkar (1999[Sarkar, B. (1999). Chem. Rev. 99, 2535-2544.]); Louhibi et al. (2007[Louhibi, S., Yacouta, A., Vendier, L., Costes, J. P. & Tuchagues, J. P. (2007). Polyhedron, 26, 3448-3454.]); Kui et al. (2009[Kui, C., Zheng, Q. Z., Qian, Y., Shi, L., Jing Zhao, J. & Zhu, H. (2009). Bioorg. Med. Chem. 7, 7861-7871.]).

[Scheme 1]

Experimental

Crystal data
  • C17H18N2O5·H2O

  • Mr = 348.35

  • Orthorhombic, P n m a

  • a = 12.8969 (10) Å

  • b = 28.001 (2) Å

  • c = 4.5330 (4) Å

  • V = 1637.0 (2) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.11 mm−1

  • T = 150 K

  • 0.38 × 0.12 × 0.04 mm

Data collection
  • Bruker APEXII diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2011[Bruker (2011). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.877, Tmax = 0.996

  • 7880 measured reflections

  • 1904 independent reflections

  • 1195 reflections with I > 2σ(I)

  • Rint = 0.062

Refinement
  • R[F2 > 2σ(F2)] = 0.048

  • wR(F2) = 0.123

  • S = 1.04

  • 1904 reflections

  • 124 parameters

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

  • Δρmax = 0.21 e Å−3

  • Δρmin = −0.23 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O1—H1⋯O1Wi 0.96 (3) 1.82 (3) 2.778 (3) 179 (3)
O1W—H1W⋯O6ii 0.92 (2) 1.92 (2) 2.827 (2) 174 (2)
O13—H13⋯O6 0.84 1.75 2.500 (2) 147
N4—H4⋯O13iii 0.88 2.07 2.915 (2) 160
Symmetry codes: (i) [x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+{\script{1\over 2}}]; (ii) x, y, z+1; (iii) [x+{\script{1\over 2}}, y, -z+{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2011[Bruker (2011). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2011[Bruker (2011). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SIR2002 (Burla et al., 2005[Burla, M. C., Caliandro, R., Camalli, M., Carrozzini, B., Cascarano, G. L., De Caro, L., Giacovazzo, C., Polidori, G. & Spagna, R. (2005). J. Appl. Cryst. 38, 381-388.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and DIAMOND (Brandenburg & Berndt, 2001[Brandenburg, K. & Berndt, M. (2001). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and CRYSCAL (T. Roisnel, local program).

Supporting information


Comment top

The chelating agents containing in their molecular structures 2-hydroxy-1,3-diaminopropane appear in a variey of ligands such as salicylamides (Kumar & Debashis, 2006) and Schiff bases (Azam et al. 2012) or as mixture of both previous functions in the same molecular structures (Kui et al. 2009). This kind of compounds are very attractive and interesting, especially for their coordinating properties with transition metal ions as those involved in metalloenzymes where, for example, the copper complexes are participating in the process of copper transport in humans (Sarkar, 1999). So, the title compound and its analogs are currently used in the synthesis of mono- and polynuclear manganese complexes to investigate their magnetic properties (Louhibi et al., 2007). However, the resulting complexes are, in this case, often bi- or polynuclear owing to their corresponding polydentate nature (NNOOO).

Herein we report the synthesis and crystal structure of N,N-Bis-Salicylamide(2-hydroxy-1,3-diaminopropane), (I). The molecule structure of (I), and the atomic numbering used, is illustrated in Fig. 1. The asymmetric unit of (I) consists of one-half of the molecule, with the other half generated by a crystallographic mirror plane.

The crystal packing can be described by alterning layers in zigzag parallel to (100) planes (Fig. 2) and the water molecule is sandwished betwen these layers. It features O—H···O and N—H···O hydrogen bonds (Fig. 2, Table 1). A O—H···O intramolecular interaction is also observed. These interactions link the molecules within the layers and also link the layers together and reinforcing the cohesion of the structure.

Related literature top

For the synthesis of similar compounds and their complexes see: Kumar & Debashis (2006); Azam et al. (2012); Sarkar (1999); Louhibi et al. (2007); Kui et al. (2009).

Experimental top

90 mg (1.0 mmol) of 2-hydroxy-1,3-diaminopropane was dissolved in 10 ml of absolute ethanol and placed in three necked flask of 50 ml. 396 mg (2.0 mmol) of phenylsalicylate were also dissolved in the same solvent (10 ml absolute ethanol). This solution was added in one portion to the previous solution. The resulting mixture, under nitrogen atmosphere and stirring, was heated to reflux for three hours, after which the reaction mixture was filtered as hot solution. Yellow prisms were formed after some days by slow evaporation (yield 70%).

Refinement top

H1W and H1 protons were located in a difference Fourier map and refined isotropically with Uiso(H) = 1.5Ueq(O). The remaining H atoms were localized on Fourier maps but introduced in calculated positions and treated as riding on their parent atom (C,O and N) with C—H = 0.99 Å (Methylene)or 0.95 Å (aromatic) or 1.00 Å (methine), O—H = 0.84 Å and N—H = 0.88 Å; with Uiso(H) = 1.2Ueq and Uiso(H) = 1.5Ueq(hydroxy).

Computing details top

Data collection: APEX2 (Bruker, 2011); cell refinement: SAINT (Bruker, 2011); data reduction: SAINT (Bruker, 2011); program(s) used to solve structure: SIR2002 (Burla et al., 2005); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and DIAMOND (Brandenburg & Berndt, 2001); software used to prepare material for publication: WinGX (Farrugia, 2012) and CRYSCAL (T. Roisnel, local program).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound with displacement drawn at the 50% probability level. Only the contents of the asymmetric unit are numbered.
[Figure 2] Fig. 2. Alternating layers in zigzag parallel to (100) plane of (I) viewed via c axis showing hydrogen bond as dashed line [O—H···O and N—H···O interactions].
N,N'-(2-Hydroxypropane-1,3-diyl)bis(2-hydroxybenzamide) monohydrate top
Crystal data top
C17H18N2O5·H2OF(000) = 736
Mr = 348.35Dx = 1.413 Mg m3
Orthorhombic, PnmaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2nCell parameters from 951 reflections
a = 12.8969 (10) Åθ = 3.2–21.6°
b = 28.001 (2) ŵ = 0.11 mm1
c = 4.5330 (4) ÅT = 150 K
V = 1637.0 (2) Å3Prism, yellow
Z = 40.38 × 0.12 × 0.04 mm
Data collection top
Bruker APEXII
diffractometer
1195 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.062
CCD rotation images, thin slices scansθmax = 27.4°, θmin = 3.2°
Absorption correction: multi-scan
(SADABS; Bruker, 2011)
h = 1615
Tmin = 0.877, Tmax = 0.996k = 3336
7880 measured reflectionsl = 35
1904 independent reflections
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)] = 0.048Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.123H atoms treated by a mixture of independent and constrained refinement
S = 1.04 w = 1/[σ2(Fo2) + (0.0542P)2]
where P = (Fo2 + 2Fc2)/3
1904 reflections(Δ/σ)max < 0.001
124 parametersΔρmax = 0.21 e Å3
0 restraintsΔρmin = 0.23 e Å3
Crystal data top
C17H18N2O5·H2OV = 1637.0 (2) Å3
Mr = 348.35Z = 4
Orthorhombic, PnmaMo Kα radiation
a = 12.8969 (10) ŵ = 0.11 mm1
b = 28.001 (2) ÅT = 150 K
c = 4.5330 (4) Å0.38 × 0.12 × 0.04 mm
Data collection top
Bruker APEXII
diffractometer
1904 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2011)
1195 reflections with I > 2σ(I)
Tmin = 0.877, Tmax = 0.996Rint = 0.062
7880 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0480 restraints
wR(F2) = 0.123H atoms treated by a mixture of independent and constrained refinement
S = 1.04Δρmax = 0.21 e Å3
1904 reflectionsΔρmin = 0.23 e Å3
124 parameters
Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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
O10.39517 (14)0.250000.2499 (4)0.0247 (6)
O60.12018 (10)0.17317 (5)0.0499 (3)0.0305 (5)
O130.01478 (10)0.12722 (5)0.2259 (4)0.0365 (5)
N40.29166 (11)0.16318 (5)0.0274 (3)0.0222 (5)
C20.3155 (2)0.250000.0315 (6)0.0220 (8)
C30.31907 (14)0.20435 (6)0.1551 (4)0.0231 (6)
C50.19276 (14)0.15119 (6)0.0789 (4)0.0221 (6)
C70.16854 (13)0.11226 (6)0.2905 (4)0.0211 (6)
C80.24447 (14)0.08491 (6)0.4318 (4)0.0246 (6)
C90.21836 (16)0.04885 (7)0.6277 (5)0.0299 (7)
C100.11462 (16)0.03987 (7)0.6864 (5)0.0324 (7)
C110.03789 (16)0.06622 (7)0.5520 (5)0.0324 (7)
C120.06373 (14)0.10227 (7)0.3538 (5)0.0266 (6)
O1W0.08072 (15)0.250000.5613 (5)0.0345 (7)
H10.460 (2)0.250000.145 (7)0.0370*
H20.247660.250000.138380.0264*
H3A0.269820.207070.321770.0278*
H3B0.389590.200000.237080.0278*
H40.341480.145810.105450.0266*
H80.315540.091180.392630.0295*
H90.270950.030490.720840.0359*
H100.096310.015260.820910.0389*
H110.032860.059780.594560.0389*
H130.010030.149280.121990.0547*
H1W0.0926 (17)0.2238 (8)0.677 (6)0.0517*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0203 (10)0.0348 (11)0.0189 (11)0.00000.0017 (9)0.0000
O60.0194 (7)0.0361 (8)0.0359 (9)0.0012 (6)0.0039 (7)0.0057 (7)
O130.0166 (7)0.0423 (9)0.0506 (11)0.0004 (6)0.0023 (7)0.0076 (8)
N40.0185 (8)0.0223 (8)0.0258 (10)0.0002 (6)0.0017 (7)0.0005 (7)
C20.0183 (13)0.0282 (14)0.0196 (15)0.00000.0013 (12)0.0000
C30.0206 (10)0.0277 (10)0.0211 (10)0.0012 (8)0.0026 (9)0.0016 (9)
C50.0208 (9)0.0252 (10)0.0202 (10)0.0002 (8)0.0012 (9)0.0063 (9)
C70.0196 (9)0.0225 (9)0.0211 (11)0.0024 (7)0.0020 (9)0.0043 (8)
C80.0205 (10)0.0272 (10)0.0262 (11)0.0032 (7)0.0014 (9)0.0036 (9)
C90.0323 (11)0.0277 (11)0.0298 (12)0.0008 (9)0.0029 (10)0.0020 (9)
C100.0375 (12)0.0319 (12)0.0279 (13)0.0092 (9)0.0060 (10)0.0005 (10)
C110.0263 (11)0.0357 (12)0.0353 (13)0.0105 (9)0.0079 (10)0.0018 (10)
C120.0218 (10)0.0290 (11)0.0291 (12)0.0010 (8)0.0009 (10)0.0072 (9)
O1W0.0306 (11)0.0388 (12)0.0340 (14)0.00000.0103 (10)0.0000
Geometric parameters (Å, º) top
O1—C21.427 (3)C7—C81.399 (2)
O6—C51.263 (2)C7—C121.410 (2)
O13—C121.360 (2)C8—C91.386 (3)
O1—H10.96 (3)C9—C101.387 (3)
O13—H130.8400C10—C111.377 (3)
O1W—H1Wi0.92 (2)C11—C121.392 (3)
O1W—H1W0.92 (2)C2—H21.0000
N4—C51.340 (2)C3—H3B0.9900
N4—C31.462 (2)C3—H3A0.9900
N4—H40.8800C8—H80.9500
C2—C31.534 (2)C9—H90.9500
C2—C3i1.534 (2)C10—H100.9500
C5—C71.485 (2)C11—H110.9500
C2—O1—H1106.4 (18)C7—C12—C11120.32 (18)
C12—O13—H13109.00O13—C12—C7121.68 (18)
H1W—O1W—H1Wi107 (2)O13—C12—C11118.00 (17)
C3—N4—C5121.76 (14)O1—C2—H2107.00
C3—N4—H4119.00C3i—C2—H2107.00
C5—N4—H4119.00C3—C2—H2107.00
O1—C2—C3i111.17 (13)N4—C3—H3B110.00
O1—C2—C3111.17 (13)C2—C3—H3A110.00
C3—C2—C3i112.93 (19)N4—C3—H3A110.00
N4—C3—C2109.75 (15)H3A—C3—H3B108.00
O6—C5—N4120.19 (16)C2—C3—H3B110.00
N4—C5—C7119.79 (15)C7—C8—H8119.00
O6—C5—C7120.01 (16)C9—C8—H8119.00
C5—C7—C12118.60 (16)C10—C9—H9120.00
C8—C7—C12118.00 (16)C8—C9—H9120.00
C5—C7—C8123.40 (15)C9—C10—H10120.00
C7—C8—C9121.48 (17)C11—C10—H10120.00
C8—C9—C10119.29 (19)C10—C11—H11120.00
C9—C10—C11120.75 (19)C12—C11—H11120.00
C10—C11—C12120.15 (19)
C3—N4—C5—O65.8 (3)C12—C7—C8—C90.3 (3)
C3—N4—C5—C7173.61 (15)C5—C7—C12—O130.2 (3)
C5—N4—C3—C283.3 (2)C5—C7—C12—C11179.68 (18)
O1—C2—C3—N467.2 (2)C8—C7—C12—O13179.97 (19)
C3i—C2—C3—N4167.07 (16)C8—C7—C12—C110.1 (3)
O6—C5—C7—C8177.11 (17)C7—C8—C9—C100.4 (3)
O6—C5—C7—C123.1 (3)C8—C9—C10—C110.2 (3)
N4—C5—C7—C83.5 (3)C9—C10—C11—C120.2 (3)
N4—C5—C7—C12176.29 (17)C10—C11—C12—O13179.8 (2)
C5—C7—C8—C9179.93 (17)C10—C11—C12—C70.4 (3)
Symmetry code: (i) x, y+1/2, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O1Wii0.96 (3)1.82 (3)2.778 (3)179 (3)
O1W—H1W···O6iii0.92 (2)1.92 (2)2.827 (2)174 (2)
O13—H13···O60.841.752.500 (2)147
N4—H4···O13iv0.882.072.915 (2)160
Symmetry codes: (ii) x+1/2, y+1/2, z+1/2; (iii) x, y, z+1; (iv) x+1/2, y, z+1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O1Wi0.96 (3)1.82 (3)2.778 (3)179 (3)
O1W—H1W···O6ii0.92 (2)1.92 (2)2.827 (2)174 (2)
O13—H13···O60.841.752.500 (2)147
N4—H4···O13iii0.882.072.915 (2)160
Symmetry codes: (i) x+1/2, y+1/2, z+1/2; (ii) x, y, z+1; (iii) x+1/2, y, z+1/2.
 

Acknowledgements

Thanks are due to MESRS and DG–RSDT (Ministére de l'Enseignement Supérieur et de la Recherche Scientifique et la Direction Générale de la Recherche - Algeria) for financial support.

References

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First citationKui, C., Zheng, Q. Z., Qian, Y., Shi, L., Jing Zhao, J. & Zhu, H. (2009). Bioorg. Med. Chem. 7, 7861–7871.
First citationKumar, P. N. & Debashis, R. (2006). J. Chem. Res. pp. 632–635.
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First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals

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