N-[2-(4-Hydroxy­benzyl­ideneamino)­ethyl]-N-[2-(4-oxidobenzyl­idene­amino)­ethyl]­ammonium

Tian, X.-M.; Liu, G.; Feng, Y.; Wang, J.-D.

doi:10.1107/S1600536807037397

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N-[2-(4-Hydroxybenzylideneamino)ethyl]-N-[2-(4-oxidobenzylideneamino)ethyl]ammonium

X.-M. Tian, G. Liu, Y. Feng and J.-D. Wang

The title Schiff base compound, C₁₈H₂₁N₃O₂, was synthesized by a condensation reaction of 4-hydroxybenzaldehyde with diethylenetriamine. The crystal structure determination reveals that one of the terminal hydroxy groups is deprotonated while the imino group of the molecule is protonated; thus the compound is a zwitterion. The two terminal benzene rings are nearly parallel to one another, with a dihedral angle of 9.94 (6)°. Intermolecular O—H

O and N—H

O hydrogen bonding helps to stabilize the crystal structure.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807037397/xu2286sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807037397/xu2286Isup2.hkl Contains datablock I

CCDC reference: 660206

checkCIF report

Key indicators

Single-crystal X-ray study
T = 153 K
Mean (C-C) = 0.001 Å
R factor = 0.036
wR factor = 0.112
Data-to-parameter ratio = 17.0

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT309_ALERT_2_C Single Bonded Oxygen (C-O .GT. 1.3 Ang) ........         O2

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   1 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Comment top

Schiff bases are important organic compounds and their metal complexes had a variety of applications including biological, clinical, analytical and catalysis (Mohamed, 2006; Jiao & Liu, 2005). In particular, Schiff bases with nitrogen and oxygen atoms are important biological ligands (Li et al., 1999). Some Schiff base cobalt complexes can absorb molecular oxygen, they were synthesized as functional model compounds to simulate a biological oxygen carrier (Xiao et al., 1987). In our lab, the oxygenation of some cobalt complexes with Schiff bases have been investigated, and found that one molar of the complexes reacted with two molar of oxygen at room temperature (Xiao et al., 2006). As part of our ongoing investigation, the title compound has been prepared and its crystal structure is reported here.

The molecule forms a U type structure (Fig. 1). The bond lengths of N1═C7 and N3═C12 (Table 1) indicate double bonds character. The C1-benzene ring is nearly parallel to the C13-benzene ring, the dihedral angle being 9.94 (6)°. The protonation of N2-imine group make the compound crystallize in a zwitterionic form. The crystal structure is stabilized by O—H···O hydrogen bonding (Table 2).

Related literature top

For general background, see: Mohamed (2006); Jiao & Liu (2005); Li et al. (1999); Xiao et al. (2006 or??1987). For synthesis, see: Xiao et al. (2006).

Experimental top

diethylenetriamine(0.103 g, 0.001 mol) in ethyl acetate (10 ml) was dropwised to a solution of 4-hydroxybenzaldehyde (0.244 g, 0.002 mol) in ethyl acetate (20 ml) in an ice-bath, then the reaction mixture was stirred for two hours, The yellow product was isolated by filtration, washed with diethyl ether, dried and obtained 0.264 g (yield 85%) (Xiao et al., 2006). Crystals suitable for single-crystal X-ray diffraction were grown from a solution of methanol by slow evaporation. Elemental analysis, found (calculated for C₁₈H₂₁N₃O₂): C 69.18% (69.45%), H 6.51% (6.75%), N 13.45% (13.50%).

Structure description top

For general background, see: Mohamed (2006); Jiao & Liu (2005); Li et al. (1999); Xiao et al. (2006 or??1987). For synthesis, see: Xiao et al. (2006).

Computing details top

Data collection: RAPID-AUTO (Rigaku, 2004); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

Fig. 1. A view of the molecule structure of (I), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level and H atoms are shown as small spheres of arbitrary radii.

N-[2-(4-hydroxybenzylideneamino)ethyl]-N-[2-(4- oxidobenzylideneamino)ethyl]ammonium top

Crystal data top

C₁₈H₂₁N₃O₂	D_x = 1.333 Mg m⁻³
M_r = 311.38	Melting point: 453 K
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 23448 reflections
a = 11.638 (2) Å	θ = 3.2–27.5°
b = 15.667 (3) Å	µ = 0.09 mm⁻¹
c = 17.016 (3) Å	T = 153 K
V = 3102.5 (11) Å³	Block, yellow
Z = 8	0.49 × 0.47 × 0.38 mm
F(000) = 1328

Data collection top

Rigaku R-AXIS SPIDER diffractometer	3084 reflections with I > 2σ(I)
Radiation source: Rotating Anode	R_int = 0.023
Graphite monochromator	θ_max = 27.5°, θ_min = 3.2°
ω scans	h = −15→15
28871 measured reflections	k = −19→20
3560 independent reflections	l = −20→22

Refinement top

Refinement on F²	H-atom parameters constrained
Least-squares matrix: full	w = 1/[σ²(F_o²) + (0.097P)² + 1.4677P] where P = (F_o² + 2F_c²)/3
R[F² > 2σ(F²)] = 0.036	(Δ/σ)_max = 0.001
wR(F²) = 0.112	Δρ_max = 0.32 e Å⁻³
S = 1.06	Δρ_min = −0.24 e Å⁻³
3560 reflections	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
209 parameters	Extinction coefficient: 0.0026 (6)
0 restraints

Crystal data top

C₁₈H₂₁N₃O₂	V = 3102.5 (11) Å³
M_r = 311.38	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 11.638 (2) Å	µ = 0.09 mm⁻¹
b = 15.667 (3) Å	T = 153 K
c = 17.016 (3) Å	0.49 × 0.47 × 0.38 mm

Data collection top

Rigaku R-AXIS SPIDER diffractometer	3084 reflections with I > 2σ(I)
28871 measured reflections	R_int = 0.023
3560 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.036	0 restraints
wR(F²) = 0.112	H-atom parameters constrained
S = 1.06	Δρ_max = 0.32 e Å⁻³
3560 reflections	Δρ_min = −0.24 e Å⁻³
209 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

	x	y	z	U_iso*/U_eq
O1	0.31037 (6)	0.14542 (5)	0.55715 (4)	0.02288 (18)
H1A	0.3662	0.1396	0.5148	0.034*
O2	0.94930 (6)	0.35847 (5)	0.55366 (4)	0.02240 (18)
N1	0.47454 (7)	0.12911 (5)	0.91717 (5)	0.02032 (19)
N2	0.62800 (6)	0.25607 (5)	0.98495 (5)	0.01873 (19)
H2A	0.6778	0.2263	0.9534	0.028*
H2C	0.5780	0.2862	0.9560	0.028*
N3	0.79044 (7)	0.37646 (5)	0.91501 (5)	0.02038 (19)
C1	0.35115 (9)	0.14906 (6)	0.76874 (6)	0.0209 (2)
H1B	0.3124	0.1697	0.8140	0.025*
C2	0.30268 (9)	0.16082 (6)	0.69552 (6)	0.0210 (2)
H2B	0.2309	0.1893	0.6910	0.025*
C3	0.35837 (8)	0.13108 (6)	0.62770 (5)	0.0180 (2)
C4	0.46222 (8)	0.08697 (6)	0.63589 (5)	0.0191 (2)
H4A	0.4998	0.0646	0.5908	0.023*
C5	0.51049 (9)	0.07584 (6)	0.70980 (6)	0.0193 (2)
H5A	0.5815	0.0464	0.7146	0.023*
C6	0.45656 (8)	0.10712 (6)	0.77718 (5)	0.0182 (2)
C7	0.51216 (8)	0.09588 (6)	0.85382 (6)	0.0188 (2)
H7A	0.5798	0.0620	0.8564	0.023*
C8	0.53900 (9)	0.11116 (6)	0.98880 (5)	0.0198 (2)
H8A	0.6124	0.0829	0.9751	0.024*
H8B	0.4943	0.0717	1.0224	0.024*
C9	0.56376 (8)	0.19273 (6)	1.03400 (5)	0.0183 (2)
H9A	0.4903	0.2184	1.0515	0.022*
H9B	0.6095	0.1789	1.0814	0.022*
C10	0.69938 (8)	0.31620 (6)	1.03268 (5)	0.0187 (2)
H10A	0.7717	0.2876	1.0482	0.022*
H10B	0.6573	0.3316	1.0812	0.022*
C11	0.72732 (9)	0.39669 (6)	0.98682 (5)	0.0203 (2)
H11A	0.6551	0.4267	0.9731	0.024*
H11B	0.7740	0.4353	1.0199	0.024*
C12	0.75025 (8)	0.40705 (6)	0.85139 (6)	0.0188 (2)
H12A	0.6815	0.4396	0.8539	0.023*
C13	0.80451 (8)	0.39474 (6)	0.77449 (5)	0.0178 (2)
C14	0.74795 (8)	0.42303 (6)	0.70696 (5)	0.0192 (2)
H14A	0.6753	0.4503	0.7117	0.023*
C15	0.79631 (9)	0.41193 (6)	0.63302 (5)	0.0190 (2)
H15A	0.7567	0.4322	0.5879	0.023*
C16	0.90284 (9)	0.37112 (6)	0.62407 (5)	0.0176 (2)
C17	0.96003 (8)	0.34366 (6)	0.69268 (6)	0.0203 (2)
H17A	1.0329	0.3167	0.6884	0.024*
C18	0.91180 (9)	0.35543 (6)	0.76583 (6)	0.0200 (2)
H18A	0.9521	0.3365	0.8112	0.024*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0195 (4)	0.0323 (4)	0.0168 (3)	0.0039 (3)	−0.0027 (3)	0.0013 (3)
O2	0.0206 (4)	0.0307 (4)	0.0159 (3)	0.0027 (3)	0.0029 (3)	−0.0011 (3)
N1	0.0177 (4)	0.0252 (4)	0.0180 (4)	−0.0004 (3)	−0.0020 (3)	0.0003 (3)
N2	0.0175 (4)	0.0252 (4)	0.0136 (4)	−0.0030 (3)	−0.0001 (3)	−0.0005 (3)
N3	0.0179 (4)	0.0251 (4)	0.0182 (4)	−0.0013 (3)	0.0031 (3)	−0.0019 (3)
C1	0.0186 (5)	0.0251 (5)	0.0188 (5)	0.0013 (4)	0.0020 (3)	−0.0028 (4)
C2	0.0164 (5)	0.0244 (5)	0.0221 (5)	0.0033 (4)	−0.0006 (3)	−0.0014 (4)
C3	0.0171 (5)	0.0189 (4)	0.0179 (4)	−0.0029 (3)	−0.0012 (3)	0.0010 (3)
C4	0.0184 (5)	0.0215 (5)	0.0173 (4)	0.0004 (4)	0.0019 (3)	−0.0007 (3)
C5	0.0167 (5)	0.0203 (4)	0.0210 (5)	0.0022 (4)	0.0006 (3)	0.0005 (3)
C6	0.0179 (5)	0.0190 (4)	0.0178 (4)	−0.0018 (3)	−0.0007 (3)	0.0006 (3)
C7	0.0168 (5)	0.0198 (4)	0.0199 (5)	−0.0005 (3)	−0.0006 (3)	0.0012 (3)
C8	0.0185 (5)	0.0222 (5)	0.0187 (4)	0.0003 (4)	−0.0017 (3)	0.0014 (4)
C9	0.0172 (5)	0.0238 (5)	0.0139 (4)	−0.0006 (4)	0.0008 (3)	0.0016 (3)
C10	0.0165 (5)	0.0255 (5)	0.0140 (4)	−0.0014 (4)	−0.0006 (3)	−0.0028 (3)
C11	0.0190 (5)	0.0232 (5)	0.0188 (5)	−0.0004 (4)	0.0030 (3)	−0.0034 (4)
C12	0.0167 (5)	0.0189 (4)	0.0208 (5)	−0.0011 (3)	0.0022 (3)	−0.0019 (3)
C13	0.0176 (5)	0.0180 (4)	0.0178 (5)	−0.0018 (3)	0.0017 (3)	−0.0006 (3)
C14	0.0161 (5)	0.0197 (4)	0.0219 (5)	0.0013 (3)	−0.0004 (4)	−0.0006 (4)
C15	0.0188 (5)	0.0210 (4)	0.0171 (4)	−0.0002 (4)	−0.0030 (3)	0.0010 (3)
C16	0.0182 (5)	0.0183 (4)	0.0164 (4)	−0.0032 (3)	0.0011 (3)	−0.0009 (3)
C17	0.0155 (5)	0.0242 (5)	0.0211 (5)	0.0028 (4)	0.0005 (3)	0.0007 (4)
C18	0.0183 (5)	0.0242 (5)	0.0175 (4)	0.0008 (4)	−0.0011 (3)	0.0019 (3)

Geometric parameters (Å, º) top

O1—C3	1.3430 (11)	C8—C9	1.5192 (13)
O1—H1A	0.9745	C8—H8A	0.9900
O2—C16	1.3293 (11)	C8—H8B	0.9900
N1—C7	1.2747 (13)	C9—H9A	0.9900
N1—C8	1.4586 (12)	C9—H9B	0.9900
N2—C10	1.4957 (12)	C10—C11	1.5183 (14)
N2—C9	1.4968 (12)	C10—H10A	0.9900
N2—H2A	0.9170	C10—H10B	0.9900
N2—H2C	0.8972	C11—H11A	0.9900
N3—C12	1.2730 (13)	C11—H11B	0.9900
N3—C11	1.4605 (12)	C12—C13	1.4656 (13)
C1—C2	1.3801 (14)	C12—H12A	0.9500
C1—C6	1.3990 (14)	C13—C14	1.3965 (13)
C1—H1B	0.9500	C13—C18	1.4000 (14)
C2—C3	1.4031 (13)	C14—C15	1.3892 (13)
C2—H2B	0.9500	C14—H14A	0.9500
C3—C4	1.3992 (14)	C15—C16	1.4032 (14)
C4—C5	1.3883 (13)	C15—H15A	0.9500
C4—H4A	0.9500	C16—C17	1.4111 (13)
C5—C6	1.3959 (13)	C17—C18	1.3778 (13)
C5—H5A	0.9500	C17—H17A	0.9500
C6—C7	1.4666 (13)	C18—H18A	0.9500
C7—H7A	0.9500

C3—O1—H1A	111.6	C8—C9—H9A	109.3
C7—N1—C8	116.82 (9)	N2—C9—H9B	109.3
C10—N2—C9	113.08 (7)	C8—C9—H9B	109.3
C10—N2—H2A	106.7	H9A—C9—H9B	107.9
C9—N2—H2A	107.8	N2—C10—C11	111.28 (7)
C10—N2—H2C	109.1	N2—C10—H10A	109.4
C9—N2—H2C	109.3	C11—C10—H10A	109.4
H2A—N2—H2C	110.8	N2—C10—H10B	109.4
C12—N3—C11	116.42 (9)	C11—C10—H10B	109.4
C2—C1—C6	120.91 (9)	H10A—C10—H10B	108.0
C2—C1—H1B	119.5	N3—C11—C10	110.95 (8)
C6—C1—H1B	119.5	N3—C11—H11A	109.4
C1—C2—C3	120.63 (9)	C10—C11—H11A	109.4
C1—C2—H2B	119.7	N3—C11—H11B	109.4
C3—C2—H2B	119.7	C10—C11—H11B	109.4
O1—C3—C4	122.06 (9)	H11A—C11—H11B	108.0
O1—C3—C2	119.18 (9)	N3—C12—C13	123.46 (9)
C4—C3—C2	118.75 (9)	N3—C12—H12A	118.3
C5—C4—C3	120.11 (9)	C13—C12—H12A	118.3
C5—C4—H4A	119.9	C14—C13—C18	118.25 (8)
C3—C4—H4A	119.9	C14—C13—C12	119.33 (9)
C4—C5—C6	121.20 (9)	C18—C13—C12	122.42 (9)
C4—C5—H5A	119.4	C15—C14—C13	120.97 (9)
C6—C5—H5A	119.4	C15—C14—H14A	119.5
C5—C6—C1	118.35 (9)	C13—C14—H14A	119.5
C5—C6—C7	119.34 (9)	C14—C15—C16	120.88 (9)
C1—C6—C7	122.31 (9)	C14—C15—H15A	119.6
N1—C7—C6	123.47 (9)	C16—C15—H15A	119.6
N1—C7—H7A	118.3	O2—C16—C15	121.68 (8)
C6—C7—H7A	118.3	O2—C16—C17	120.56 (9)
N1—C8—C9	111.00 (8)	C15—C16—C17	117.76 (8)
N1—C8—H8A	109.4	C18—C17—C16	120.96 (9)
C9—C8—H8A	109.4	C18—C17—H17A	119.5
N1—C8—H8B	109.4	C16—C17—H17A	119.5
C9—C8—H8B	109.4	C17—C18—C13	121.15 (9)
H8A—C8—H8B	108.0	C17—C18—H18A	119.4
N2—C9—C8	111.72 (7)	C13—C18—H18A	119.4
N2—C9—H9A	109.3

C6—C1—C2—C3	−0.18 (16)	C9—N2—C10—C11	−159.33 (8)
C1—C2—C3—O1	−178.33 (9)	C12—N3—C11—C10	127.76 (9)
C1—C2—C3—C4	1.95 (15)	N2—C10—C11—N3	−59.52 (10)
O1—C3—C4—C5	178.05 (9)	C11—N3—C12—C13	178.42 (8)
C2—C3—C4—C5	−2.24 (14)	N3—C12—C13—C14	173.33 (9)
C3—C4—C5—C6	0.78 (15)	N3—C12—C13—C18	−6.70 (15)
C4—C5—C6—C1	0.99 (14)	C18—C13—C14—C15	0.49 (14)
C4—C5—C6—C7	−178.39 (9)	C12—C13—C14—C15	−179.54 (9)
C2—C1—C6—C5	−1.29 (15)	C13—C14—C15—C16	0.70 (15)
C2—C1—C6—C7	178.07 (9)	C14—C15—C16—O2	178.66 (9)
C8—N1—C7—C6	179.39 (8)	C14—C15—C16—C17	−1.43 (14)
C5—C6—C7—N1	173.30 (9)	O2—C16—C17—C18	−179.09 (9)
C1—C6—C7—N1	−6.06 (15)	C15—C16—C17—C18	1.00 (14)
C7—N1—C8—C9	130.85 (9)	C16—C17—C18—C13	0.18 (15)
C10—N2—C9—C8	−153.53 (8)	C14—C13—C18—C17	−0.93 (14)
N1—C8—C9—N2	−57.22 (10)	C12—C13—C18—C17	179.10 (9)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···O2ⁱ	0.97	1.51	2.4846 (11)	173
N2—H2A···O1ⁱⁱ	0.92	2.00	2.8325 (12)	149
N2—H2C···O2ⁱⁱⁱ	0.90	1.88	2.7075 (12)	152

Symmetry codes: (i) x−1/2, −y+1/2, −z+1; (ii) x+1/2, y, −z+3/2; (iii) x−1/2, y, −z+3/2.

Experimental details

Crystal data
Chemical formula	C₁₈H₂₁N₃O₂
M_r	311.38
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	153
a, b, c (Å)	11.638 (2), 15.667 (3), 17.016 (3)
V (Å³)	3102.5 (11)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.49 × 0.47 × 0.38

Data collection
Diffractometer	Rigaku R-AXIS SPIDER
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	28871, 3560, 3084
R_int	0.023
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.036, 0.112, 1.06
No. of reflections	3560
No. of parameters	209
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.32, −0.24

Computer programs: RAPID-AUTO (Rigaku, 2004), RAPID-AUTO, CrystalStructure (Rigaku/MSC, 2004), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 (Farrugia, 1997), WinGX (Farrugia, 1999).

Selected bond lengths (Å) top

O1—C3	1.3430 (11)	N1—C7	1.2747 (13)
O2—C16	1.3293 (11)	N3—C12	1.2730 (13)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···O2ⁱ	0.97	1.51	2.4846 (11)	173
N2—H2A···O1ⁱⁱ	0.92	2.00	2.8325 (12)	149
N2—H2C···O2ⁱⁱⁱ	0.90	1.88	2.7075 (12)	152

Symmetry codes: (i) x−1/2, −y+1/2, −z+1; (ii) x+1/2, y, −z+3/2; (iii) x−1/2, y, −z+3/2.

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