Bis{(E)-3-[(2-hy­droxy­benzyl­idene)amino]­prop­yl}ammonium chloride

AlDamen, M.A.; Haddad, S.F.

doi:10.1107/S1600536812045424

organic compounds

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ISSN: 2056-9890

Volume 68| Part 12| December 2012| Page o3314

doi:10.1107/S1600536812045424

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Bis{(E)-3-[(2-hydroxybenzylidene)amino]propyl}ammonium chloride

Murad A. AlDamen ^a ^* and Salim F. Haddad ^a

^aDepartment of Chemistry, The University of Jordan, Amman 11942, Jordan
^*Correspondence e-mail: maldamen@ju.edu.jo

(Received 6 September 2012; accepted 2 November 2012; online 10 November 2012)

The title salt, C₂₀H₂₆N₃O₂⁺·Cl⁻, lies across a twofold crystallographic axis with the central N atom of the cation and the chloride anion sitting on this axis, Z′ = 0.5. There is an intramolecular hydrogen bond between the hydroxy H atom and the imino N atom. The chloride anion and the cation are connected into chains along the a axis by an N—H⋯Cl hydrogen bond. In the crystal, the chains are linked via C—H⋯Cl interactions forming two-dimensional networks lying parallel to (101).

Related literature

For applications of similar ligands, see: Taha et al. (2011a ,b ). For analgous structures, see: Ramazani et al. (2006 ); Cheng et al. (2009 ); Chen et al. (2011 ); Pavel et al. (2007 ).

Experimental

Crystal data

C₂₀H₂₆N₃O₂⁺·Cl⁻
M_r = 375.88
Orthorhombic, P c c n
a = 4.9848 (3) Å
b = 38.714 (2) Å
c = 10.3299 (7) Å
V = 1993.5 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.21 mm⁻¹
T = 100 K
0.52 × 0.37 × 0.04 mm

Data collection

Oxford Diffraction Xcalibur (Eos, Gemini ultra) diffractometer
Absorption correction: analytical [CrysAlis PRO (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ), based on expressions derived from Clark & Reid (1995 )] T_min = 0.94, T_max = 0.992
8874 measured reflections
2040 independent reflections
1654 reflections with I > 2σ(I)
R_int = 0.049

Refinement

R[F² > 2σ(F²)] = 0.076
wR(F²) = 0.150
S = 1.21
2040 reflections
119 parameters
Only H-atom displacement parameters refined
Δρ_max = 0.39 e Å⁻³
Δρ_min = −0.88 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯Cl1	0.91	2.22	3.128 (2)	176
O1—H1⋯N2	0.97	1.70	2.577 (4)	148
C1—H1C⋯Cl1ⁱ	0.97	2.70	3.642 (4)	164
Symmetry code: (i) $[-x-{\script{1\over 2}}, y, z-{\script{1\over 2}}]$ .

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: OLEX2 (Dolomanov et al., 2009 ); software used to prepare material for publication: OLEX2.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812045424/go2068sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812045424/go2068Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812045424/go2068Isup3.cml

checkCIF report

Comment top

Tetradentate Schiff bases are flexible ligands and difficult to crystallize and most of the crystal structures published for these ligands are complexes with transition metals or anthanides/actinides.

As far as we can determine there are no published structures for this type of ligand and published data for these types of ligand with antimicrobial or of interst because of their optical properies have been were has been obtained from solid state techniques like NMR or elemental analysis Taha et al. (2011a); Taha et al. (2011b). We crystallized (I) as salt. (Fig. 1). The molecule sits across a two-fold crystallographic axis with the ammonium nitrogen atom, N1, and the Cl anion sitting on the two-fold axis.

The bond lengths of N1—C1 and N2—C3 are 1.501 (4) and 1.456 (4) respectively indicate that these are single bonds and the bond length of N2—C4 (1.273 (4) Å) shows that this is a double bond exhibits a double bond. The distances are in agreement with other salicylic and dipropylamino ligands and complexes found in literature (Ramazani et al. (2006), Cheng et al. (2009), Pavel et al. (2007) & Chen et al. (2011)).

There is an intramolecular hydrogen bond between the phenolic oxygen, O1 and N2, Table 1, Fig1 The N1—HH1A···Cl1 hydrogen bond connects the chloride ion to two adjacent ligands to form chains which run parallel to the a axis, Table 1 and Fig. 1. In addition there is a short contact between C1 and Cl1, Table 1. There are no C–H···π interactions nor is there any π-π stacking.

Related literature top

For applications of similar ligands, see: Taha et al. (2011a,b). For analgous structures, see: Ramazani et al. (2006); Cheng et al. (2009); Chen et al. (2011); Pavel et al. (2007).

Experimental top

Facile condensation of 3,3 –Diaminodipropylamine and salicylaldehyde 1:2 molar ratio afforded a neutral condensate as following:

3,3 –Diaminodipropylamine (30 ml, 0.208 mol) was added dropwise to a solution of salicylaldehyde (50.7 g, 0.416 mol) in absolute ethanol (250 ml); the solution became instantly yellow. The mixture was heated for 1 h at 50°C. Evaporation of the solvent under reduced pressure afforded the desired compound in 95% yield as yellow oil. The obtained Schiff base was then mixed with cyanuric acid in ethanol with few drops of 1M HCl added. The mixture then stir heated (40°C) for 24 then filtered. After few days crystals suitable for X-ray diffraction were formed.

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2009); cell refinement: CrysAlis PRO (Oxford Diffraction, 2009); data reduction: CrysAlis PRO (Oxford Diffraction, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

Figures top

	Fig. 1. Asymmetric units and the atom-numbering schemes for (I) with thermal displacement ellipsoids at 30% probability (except hydrogens).
	Fig. 2. View of the molecular acking diagram, view perpendicular to the bc plane.

Bis{(E)-3-[(2-hydroxybenzylidene)amino]propyl}ammonium chloride top

Crystal data top

C₂₀H₂₆N₃O₂⁺·Cl⁻	D_x = 1.252 Mg m⁻³
M_r = 375.88	Mo Kα radiation, λ = 0.7107 Å
Orthorhombic, Pccn	Cell parameters from 2556 reflections
a = 4.9848 (3) Å	θ = 3.7–26.3°
b = 38.714 (2) Å	µ = 0.21 mm⁻¹
c = 10.3299 (7) Å	T = 100 K
V = 1993.5 (2) Å³	Prism, white
Z = 4	0.52 × 0.37 × 0.04 mm
F(000) = 800

Data collection top

Oxford Diffraction Xcalibur (Eos, Gemini ultra) diffractometer	2040 independent reflections
Radiation source: fine-focus sealed tube	1654 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.049
Detector resolution: 16.0122 pixels mm^-1	θ_max = 26.4°, θ_min = 4.0°
ω scans	h = −6→5
Absorption correction: analytical [CrysAlis PRO (Oxford Diffraction, 2009), based on expressions derived from Clark & Reid (1995)]	k = −48→48
T_min = 0.94, T_max = 0.992	l = −12→12
8874 measured reflections

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)] = 0.076	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.150	Only H-atom displacement parameters refined
S = 1.21	w = 1/[σ²(F_o²) + (0.0141P)² + 6.1394P] where P = (F_o² + 2F_c²)/3
2040 reflections	(Δ/σ)_max < 0.001
119 parameters	Δρ_max = 0.39 e Å⁻³
0 restraints	Δρ_min = −0.88 e Å⁻³

Crystal data top

C₂₀H₂₆N₃O₂⁺·Cl⁻	V = 1993.5 (2) Å³
M_r = 375.88	Z = 4
Orthorhombic, Pccn	Mo Kα radiation
a = 4.9848 (3) Å	µ = 0.21 mm⁻¹
b = 38.714 (2) Å	T = 100 K
c = 10.3299 (7) Å	0.52 × 0.37 × 0.04 mm

Data collection top

Oxford Diffraction Xcalibur (Eos, Gemini ultra) diffractometer	2040 independent reflections
Absorption correction: analytical [CrysAlis PRO (Oxford Diffraction, 2009), based on expressions derived from Clark & Reid (1995)]	1654 reflections with I > 2σ(I)
T_min = 0.94, T_max = 0.992	R_int = 0.049
8874 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.076	0 restraints
wR(F²) = 0.150	Only H-atom displacement parameters refined
S = 1.21	Δρ_max = 0.39 e Å⁻³
2040 reflections	Δρ_min = −0.88 e Å⁻³
119 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O1	−0.1873 (5)	0.13196 (7)	0.8454 (3)	0.0340 (7)
H1	−0.0740	0.1460	0.7900	0.051*
N1	0.2500	0.2500	0.5049 (4)	0.0174 (8)
H1A	0.1010	0.2508	0.5560	0.021*
N2	0.1804 (6)	0.14754 (7)	0.6799 (3)	0.0229 (7)
C1	0.2328 (7)	0.21793 (8)	0.4236 (3)	0.0213 (7)
H1B	0.4094	0.2126	0.3897	0.026*
H1C	0.1150	0.2223	0.3507	0.026*
C2	0.1289 (7)	0.18696 (8)	0.4984 (3)	0.0230 (8)
H2A	0.0861	0.1688	0.4373	0.028*
H2B	−0.0364	0.1935	0.5414	0.028*
C3	0.3212 (7)	0.17249 (9)	0.5993 (3)	0.0236 (8)
H3A	0.4716	0.1614	0.5566	0.028*
H3B	0.3901	0.1911	0.6526	0.028*
C4	0.2480 (7)	0.11586 (8)	0.6762 (3)	0.0226 (7)
H4	0.3885	0.1092	0.6225	0.027*
C5	0.1112 (7)	0.08970 (9)	0.7539 (3)	0.0234 (8)
C6	−0.1012 (7)	0.09900 (9)	0.8369 (3)	0.0257 (8)
C7	−0.2244 (9)	0.07364 (10)	0.9119 (4)	0.0345 (9)
H7	−0.3635	0.0796	0.9676	0.041*
C8	−0.1417 (9)	0.03980 (11)	0.9042 (4)	0.0388 (10)
H8	−0.2260	0.0231	0.9547	0.047*
C9	0.0656 (9)	0.03018 (10)	0.8224 (4)	0.0394 (10)
H9	0.1205	0.0073	0.8177	0.047*
C10	0.1893 (8)	0.05520 (9)	0.7478 (4)	0.0325 (9)
H10	0.3278	0.0489	0.6924	0.039*
Cl1	−0.2500	0.2500	0.68790 (11)	0.0223 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0353 (16)	0.0380 (14)	0.0286 (15)	0.0007 (12)	0.0106 (13)	−0.0020 (12)
N1	0.0110 (18)	0.0282 (19)	0.0131 (19)	−0.0011 (17)	0.000	0.000
N2	0.0248 (16)	0.0259 (14)	0.0180 (15)	−0.0025 (12)	−0.0038 (13)	−0.0005 (12)
C1	0.0195 (16)	0.0289 (17)	0.0156 (16)	−0.0015 (15)	−0.0012 (14)	−0.0030 (13)
C2	0.0200 (18)	0.0259 (17)	0.0230 (19)	−0.0021 (14)	−0.0039 (15)	−0.0010 (14)
C3	0.0235 (19)	0.0263 (17)	0.0208 (18)	−0.0040 (14)	−0.0011 (15)	−0.0029 (14)
C4	0.0210 (17)	0.0310 (17)	0.0158 (16)	0.0000 (15)	0.0007 (15)	−0.0017 (14)
C5	0.0202 (18)	0.0298 (18)	0.0201 (18)	−0.0024 (14)	−0.0037 (15)	0.0004 (14)
C6	0.0252 (19)	0.0342 (19)	0.0178 (18)	−0.0038 (16)	−0.0034 (15)	−0.0008 (15)
C7	0.031 (2)	0.048 (2)	0.024 (2)	−0.0092 (19)	0.0037 (18)	0.0034 (17)
C8	0.037 (2)	0.045 (2)	0.035 (2)	−0.0136 (19)	−0.0037 (19)	0.0133 (19)
C9	0.045 (3)	0.030 (2)	0.043 (3)	0.0001 (18)	0.000 (2)	0.0099 (18)
C10	0.032 (2)	0.0319 (19)	0.033 (2)	0.0000 (17)	0.0020 (18)	0.0014 (17)
Cl1	0.0132 (5)	0.0368 (6)	0.0169 (5)	−0.0037 (5)	0.000	0.000

Geometric parameters (Å, º) top

O1—C6	1.349 (4)	C3—H3B	0.9700
O1—H1	0.9705	C4—C5	1.461 (5)
N1—C1ⁱ	1.501 (4)	C4—H4	0.9300
N1—C1	1.501 (4)	C5—C10	1.393 (5)
N1—H1A	0.9117	C5—C6	1.409 (5)
N2—C4	1.272 (4)	C6—C7	1.394 (5)
N2—C3	1.456 (4)	C7—C8	1.376 (6)
C1—C2	1.518 (4)	C7—H7	0.9300
C1—H1B	0.9700	C8—C9	1.386 (6)
C1—H1C	0.9700	C8—H8	0.9300
C2—C3	1.522 (5)	C9—C10	1.383 (5)
C2—H2A	0.9700	C9—H9	0.9300
C2—H2B	0.9700	C10—H10	0.9300
C3—H3A	0.9700

C6—O1—H1	107.8	H3A—C3—H3B	108.2
C1ⁱ—N1—C1	112.0 (3)	N2—C4—C5	121.8 (3)
C1ⁱ—N1—H1A	110.0	N2—C4—H4	119.1
C1—N1—H1A	107.8	C5—C4—H4	119.1
C4—N2—C3	119.6 (3)	C10—C5—C6	118.8 (3)
N1—C1—C2	112.8 (3)	C10—C5—C4	120.6 (3)
N1—C1—H1B	109.0	C6—C5—C4	120.5 (3)
C2—C1—H1B	109.0	O1—C6—C7	119.3 (3)
N1—C1—H1C	109.0	O1—C6—C5	121.3 (3)
C2—C1—H1C	109.0	C7—C6—C5	119.3 (3)
H1B—C1—H1C	107.8	C8—C7—C6	120.4 (4)
C1—C2—C3	115.1 (3)	C8—C7—H7	119.8
C1—C2—H2A	108.5	C6—C7—H7	119.8
C3—C2—H2A	108.5	C7—C8—C9	121.0 (4)
C1—C2—H2B	108.5	C7—C8—H8	119.5
C3—C2—H2B	108.5	C9—C8—H8	119.5
H2A—C2—H2B	107.5	C10—C9—C8	119.0 (4)
N2—C3—C2	109.4 (3)	C10—C9—H9	120.5
N2—C3—H3A	109.8	C8—C9—H9	120.5
C2—C3—H3A	109.8	C9—C10—C5	121.5 (4)
N2—C3—H3B	109.8	C9—C10—H10	119.3
C2—C3—H3B	109.8	C5—C10—H10	119.3

C1ⁱ—N1—C1—C2	−161.9 (3)	C10—C5—C6—C7	1.0 (5)
N1—C1—C2—C3	−70.5 (4)	C4—C5—C6—C7	−178.7 (3)
C4—N2—C3—C2	114.2 (3)	O1—C6—C7—C8	179.5 (4)
C1—C2—C3—N2	169.3 (3)	C5—C6—C7—C8	−0.6 (6)
C3—N2—C4—C5	−179.2 (3)	C6—C7—C8—C9	0.2 (6)
N2—C4—C5—C10	180.0 (3)	C7—C8—C9—C10	0.0 (6)
N2—C4—C5—C6	−0.4 (5)	C8—C9—C10—C5	0.4 (6)
C10—C5—C6—O1	−179.2 (3)	C6—C5—C10—C9	−0.8 (6)
C4—C5—C6—O1	1.2 (5)	C4—C5—C10—C9	178.8 (4)

Symmetry code: (i) −x+1/2, −y+1/2, z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···Cl1	0.91	2.22	3.128 (2)	176
O1—H1···N2	0.97	1.70	2.577 (4)	148
C1—H1C···Cl1ⁱⁱ	0.97	2.70	3.642 (4)	164

Symmetry code: (ii) −x−1/2, y, z−1/2.

Experimental details

Crystal data
Chemical formula	C₂₀H₂₆N₃O₂⁺·Cl⁻
M_r	375.88
Crystal system, space group	Orthorhombic, Pccn
Temperature (K)	100
a, b, c (Å)	4.9848 (3), 38.714 (2), 10.3299 (7)
V (Å³)	1993.5 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.21
Crystal size (mm)	0.52 × 0.37 × 0.04

Data collection
Diffractometer	Oxford Diffraction Xcalibur (Eos, Gemini ultra) diffractometer
Absorption correction	Analytical [CrysAlis PRO (Oxford Diffraction, 2009), based on expressions derived from Clark & Reid (1995)]
T_min, T_max	0.94, 0.992
No. of measured, independent and observed [I > 2σ(I)] reflections	8874, 2040, 1654
R_int	0.049
(sin θ/λ)_max (Å⁻¹)	0.625

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.076, 0.150, 1.21
No. of reflections	2040
No. of parameters	119
H-atom treatment	Only H-atom displacement parameters refined
Δρ_max, Δρ_min (e Å⁻³)	0.39, −0.88

Computer programs: CrysAlis PRO (Oxford Diffraction, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), OLEX2 (Dolomanov et al., 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···Cl1	0.91	2.22	3.128 (2)	176
O1—H1···N2	0.97	1.70	2.577 (4)	148
C1—H1C···Cl1ⁱ	0.97	2.70	3.642 (4)	164

Symmetry code: (i) −x−1/2, y, z−1/2.

References

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doi:10.1107/S1600536812045424

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