Bis{(E)-3-[(2-hy-droxy-benzyl-idene)amino]-prop-yl}ammonium chloride.

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 intra-molecular hydrogen bond between the hy-droxy 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 = 375.88

Orthorhombic,

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 ▶), 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[F 2 > 2σ(F 2)] = 0.076

wR(F 2) = 0.150

S = 1.21

2040 reflections

119 parameters

Only H-atom displacement parameters refined

Δρmax = 0.39 e Å−3

Δρmin = −0.88 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 ▶); 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.

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812045424/go2068sup1.cif

Click here for additional data file.

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

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812045424/go2068Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C20H26N3O2+·Cl−	Dx = 1.252 Mg m−3
Mr = 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

Oxford Diffraction Xcalibur (Eos, Gemini ultra) diffractometer	2040 independent reflections
Radiation source: fine-focus sealed tube	1654 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.049
Detector resolution: 16.0122 pixels mm-1	θmax = 26.4°, θmin = 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
Tmin = 0.94, Tmax = 0.992	l = −12→12
8874 measured reflections

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(Fo2) + (0.0141P)2 + 6.1394P] where P = (Fo2 + 2Fc2)/3
2040 reflections	(Δ/σ)max < 0.001
119 parameters	Δρmax = 0.39 e Å−3
0 restraints	Δρmin = −0.88 e Å−3

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.

	x	y	z	Uiso*/Ueq
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)

	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

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)

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

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) .