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

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); Azam et al. (2012); Sarkar (1999); Louhibi et al. (2007); Kui et al. (2009).

Experimental

Crystal data

• C₁₇H₁₈N₂O₅·H₂O

• M_r = 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) ų

• 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) T_min = 0.877, T_max = 0.996

• 7880 measured reflections

• 1904 independent reflections

• 1195 reflections with I > 2σ(I)

• R_int = 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

• Δρ_max = 0.21 e Å⁻³

• Δρ_min = −0.23 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O1W^i	0.96 (3)	1.82 (3)	2.778 (3)	179 (3)
O1W—H1W⋯O6^ii	0.92 (2)	1.92 (2)	2.827 (2)	174 (2)
O13—H13⋯O6	0.84	1.75	2.500 (2)	147
N4—H4⋯O13^iii	0.88	2.07	2.915 (2)	160
Symmetry codes: (i) ; (ii) x, y, z+1; (iii) .

Data collection: APEX2 (Bruker, 2011); cell refinement: SAINT (Bruker, 2011); data reduction: SAINT; 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).

Supporting information

S1. Comment

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

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).

S2. Experimental

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%).

S3. Refinement

H1W and H1 protons were located in a difference Fourier map and refined isotropically with U_iso(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 U_iso(H) = 1.2U_eq and U_iso(H) = 1.5U_eq(hydroxy).

Computing details

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

	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.
	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

Crystal data

C17H18N2O5·H2O	F(000) = 736
Mr = 348.35	Dx = 1.413 Mg m^−3
Orthorhombic, Pnma	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2n	Cell parameters from 951 reflections
a = 12.8969 (10) Å	θ = 3.2–21.6°
b = 28.001 (2) Å	µ = 0.11 mm^−1
c = 4.5330 (4) Å	T = 150 K
V = 1637.0 (2) Å^3	Prism, yellow
Z = 4	0.38 × 0.12 × 0.04 mm

Data collection

Bruker APEXII diffractometer	1195 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.062
CCD rotation images, thin slices scans	θmax = 27.4°, θmin = 3.2°
Absorption correction: multi-scan (SADABS; Bruker, 2011)	h = −16→15
Tmin = 0.877, Tmax = 0.996	k = −33→36
7880 measured reflections	l = −3→5
1904 independent reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.123	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0542P)^2] where P = (Fo^2 + 2Fc^2)/3
1904 reflections	(Δ/σ)max < 0.001
124 parameters	Δρmax = 0.21 e Å^−3
0 restraints	Δρmin = −0.23 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
O1	0.39517 (14)	0.25000	0.2499 (4)	0.0247 (6)
O6	0.12018 (10)	0.17317 (5)	−0.0499 (3)	0.0305 (5)
O13	−0.01478 (10)	0.12722 (5)	0.2259 (4)	0.0365 (5)
N4	0.29166 (11)	0.16318 (5)	0.0274 (3)	0.0222 (5)
C2	0.3155 (2)	0.25000	0.0315 (6)	0.0220 (8)
C3	0.31907 (14)	0.20435 (6)	−0.1551 (4)	0.0231 (6)
C5	0.19276 (14)	0.15119 (6)	0.0789 (4)	0.0221 (6)
C7	0.16854 (13)	0.11226 (6)	0.2905 (4)	0.0211 (6)
C8	0.24447 (14)	0.08491 (6)	0.4318 (4)	0.0246 (6)
C9	0.21836 (16)	0.04885 (7)	0.6277 (5)	0.0299 (7)
C10	0.11462 (16)	0.03987 (7)	0.6864 (5)	0.0324 (7)
C11	0.03789 (16)	0.06622 (7)	0.5520 (5)	0.0324 (7)
C12	0.06373 (14)	0.10227 (7)	0.3538 (5)	0.0266 (6)
O1W	0.08072 (15)	0.25000	0.5613 (5)	0.0345 (7)
H1	0.460 (2)	0.25000	0.145 (7)	0.0370*
H2	0.24766	0.25000	0.13838	0.0264*
H3A	0.26982	0.20707	−0.32177	0.0278*
H3B	0.38959	0.20000	−0.23708	0.0278*
H4	0.34148	0.14581	0.10545	0.0266*
H8	0.31554	0.09118	0.39263	0.0295*
H9	0.27095	0.03049	0.72084	0.0359*
H10	0.09631	0.01526	0.82091	0.0389*
H11	−0.03286	0.05978	0.59456	0.0389*
H13	0.01003	0.14928	0.12199	0.0547*
H1W	0.0926 (17)	0.2238 (8)	0.677 (6)	0.0517*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0203 (10)	0.0348 (11)	0.0189 (11)	0.0000	0.0017 (9)	0.0000
O6	0.0194 (7)	0.0361 (8)	0.0359 (9)	0.0012 (6)	−0.0039 (7)	0.0057 (7)
O13	0.0166 (7)	0.0423 (9)	0.0506 (11)	−0.0004 (6)	0.0023 (7)	0.0076 (8)
N4	0.0185 (8)	0.0223 (8)	0.0258 (10)	0.0002 (6)	0.0017 (7)	0.0005 (7)
C2	0.0183 (13)	0.0282 (14)	0.0196 (15)	0.0000	0.0013 (12)	0.0000
C3	0.0206 (10)	0.0277 (10)	0.0211 (10)	−0.0012 (8)	0.0026 (9)	0.0016 (9)
C5	0.0208 (9)	0.0252 (10)	0.0202 (10)	−0.0002 (8)	0.0012 (9)	−0.0063 (9)
C7	0.0196 (9)	0.0225 (9)	0.0211 (11)	−0.0024 (7)	0.0020 (9)	−0.0043 (8)
C8	0.0205 (10)	0.0272 (10)	0.0262 (11)	−0.0032 (7)	0.0014 (9)	−0.0036 (9)
C9	0.0323 (11)	0.0277 (11)	0.0298 (12)	−0.0008 (9)	−0.0029 (10)	−0.0020 (9)
C10	0.0375 (12)	0.0319 (12)	0.0279 (13)	−0.0092 (9)	0.0060 (10)	0.0005 (10)
C11	0.0263 (11)	0.0357 (12)	0.0353 (13)	−0.0105 (9)	0.0079 (10)	−0.0018 (10)
C12	0.0218 (10)	0.0290 (11)	0.0291 (12)	−0.0010 (8)	0.0009 (10)	−0.0072 (9)
O1W	0.0306 (11)	0.0388 (12)	0.0340 (14)	0.0000	−0.0103 (10)	0.0000

Geometric parameters (Å, º)

O1—C2	1.427 (3)	C7—C8	1.399 (2)
O6—C5	1.263 (2)	C7—C12	1.410 (2)
O13—C12	1.360 (2)	C8—C9	1.386 (3)
O1—H1	0.96 (3)	C9—C10	1.387 (3)
O13—H13	0.8400	C10—C11	1.377 (3)
O1W—H1W^i	0.92 (2)	C11—C12	1.392 (3)
O1W—H1W	0.92 (2)	C2—H2	1.0000
N4—C5	1.340 (2)	C3—H3B	0.9900
N4—C3	1.462 (2)	C3—H3A	0.9900
N4—H4	0.8800	C8—H8	0.9500
C2—C3	1.534 (2)	C9—H9	0.9500
C2—C3^i	1.534 (2)	C10—H10	0.9500
C5—C7	1.485 (2)	C11—H11	0.9500
C2—O1—H1	106.4 (18)	C7—C12—C11	120.32 (18)
C12—O13—H13	109.00	O13—C12—C7	121.68 (18)
H1W—O1W—H1W^i	107 (2)	O13—C12—C11	118.00 (17)
C3—N4—C5	121.76 (14)	O1—C2—H2	107.00
C3—N4—H4	119.00	C3^i—C2—H2	107.00
C5—N4—H4	119.00	C3—C2—H2	107.00
O1—C2—C3^i	111.17 (13)	N4—C3—H3B	110.00
O1—C2—C3	111.17 (13)	C2—C3—H3A	110.00
C3—C2—C3^i	112.93 (19)	N4—C3—H3A	110.00
N4—C3—C2	109.75 (15)	H3A—C3—H3B	108.00
O6—C5—N4	120.19 (16)	C2—C3—H3B	110.00
N4—C5—C7	119.79 (15)	C7—C8—H8	119.00
O6—C5—C7	120.01 (16)	C9—C8—H8	119.00
C5—C7—C12	118.60 (16)	C10—C9—H9	120.00
C8—C7—C12	118.00 (16)	C8—C9—H9	120.00
C5—C7—C8	123.40 (15)	C9—C10—H10	120.00
C7—C8—C9	121.48 (17)	C11—C10—H10	120.00
C8—C9—C10	119.29 (19)	C10—C11—H11	120.00
C9—C10—C11	120.75 (19)	C12—C11—H11	120.00
C10—C11—C12	120.15 (19)
C3—N4—C5—O6	5.8 (3)	C12—C7—C8—C9	0.3 (3)
C3—N4—C5—C7	−173.61 (15)	C5—C7—C12—O13	0.2 (3)
C5—N4—C3—C2	83.3 (2)	C5—C7—C12—C11	−179.68 (18)
O1—C2—C3—N4	67.2 (2)	C8—C7—C12—O13	179.97 (19)
C3^i—C2—C3—N4	−167.07 (16)	C8—C7—C12—C11	0.1 (3)
O6—C5—C7—C8	177.11 (17)	C7—C8—C9—C10	−0.4 (3)
O6—C5—C7—C12	−3.1 (3)	C8—C9—C10—C11	0.2 (3)
N4—C5—C7—C8	−3.5 (3)	C9—C10—C11—C12	0.2 (3)
N4—C5—C7—C12	176.29 (17)	C10—C11—C12—O13	179.8 (2)
C5—C7—C8—C9	−179.93 (17)	C10—C11—C12—C7	−0.4 (3)

Symmetry code: (i) x, −y+1/2, z.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O1W^ii	0.96 (3)	1.82 (3)	2.778 (3)	179 (3)
O1W—H1W···O6^iii	0.92 (2)	1.92 (2)	2.827 (2)	174 (2)
O13—H13···O6	0.84	1.75	2.500 (2)	147
N4—H4···O13^iv	0.88	2.07	2.915 (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.