2-[(E)-(2-Amino­phen­yl)imino­meth­yl]-5-(dimethyl­amino)phenol

Yu, Y.-H.; Qian, K.

doi:10.1107/S1600536809015773

organic compounds

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Volume 65| Part 6| June 2009| Page o1232

doi:10.1107/S1600536809015773

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2-[(E)-(2-Aminophenyl)iminomethyl]-5-(dimethylamino)phenol

Yan-Hong Yu ^a ^* and Kun Qian ^b

^aJiangxi Key Laboratory of Organic Chemistry, Jiangxi Science and Technology Normal University, Nanchang 330013, People's Republic of China, and ^bAcademic Administration of JiangXi University of Traditional Chinese Medicine, Nanchang 330047, People's Republic of China
^*Correspondence e-mail: yuyanhong001@yahoo.com.cn

(Received 24 April 2009; accepted 28 April 2009; online 7 May 2009)

The molecule of the title compound, C₁₇H₂₁N₃O, displays a trans configuration with respect to the C=N double bond. The dihedral angle between the planes of the two benzene rings is 50.96 (11)° and a strong intramolecular O—H⋯N hydrogen bond is present. An intermolecular N—H⋯O hydrogen-bonding interaction stabilizes the crystal structure.

Related literature

For general background to the properties of Schiff base compounds, see: Weber et al. (2007 ); Chen et al. (2008 ); May et al. (2004 ). For the structure of a related compound, see: Elmah et al. (1999 ).

Experimental

Crystal data

C₁₇H₂₁N₃O
M_r = 283.37
Orthorhombic, P 2₁ 2₁ 2₁
a = 6.5904 (13) Å
b = 12.703 (3) Å
c = 18.538 (4) Å
V = 1552.0 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 293 K
0.20 × 0.20 × 0.20 mm

Data collection

Rigaku SCXmini diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ) T_min = 0.973, T_max = 0.979
16156 measured reflections
2061 independent reflections
1996 reflections with I > 2σ(I)
R_int = 0.063

Refinement

R[F² > 2σ(F²)] = 0.058
wR(F²) = 0.176
S = 1.04
2061 reflections
194 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.13 e Å⁻³
Δρ_min = −0.14 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3B⋯O1ⁱ	0.86	2.55	3.395 (4)	167
O1—H1A⋯N2	0.86 (5)	1.82 (5)	2.638 (4)	157 (4)
Symmetry code: (i) $[-x, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick,2008); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809015773/rz2315sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809015773/rz2315Isup2.hkl

checkCIF report

Comment top

Schiff base compounds have received considerable attention for many years, primarily due to their importance in the development of coordination chemistry related to magnetism (Weber et al., 2007), catalysis (Chen et al., 2008) and biological processes (May et al.,2004). Our group is interested in the synthesis and preparation of Schiff bases. Here, we report the synthesis and crystal structure of the title compound.

The molecular structure of the title compound is shown in Fig. 1. The dihedral angle between the mean planes of the two aromatic rings is 50.96 (11)°, indicating that the Schiff-base ligand adopts a non-planar conformation. As expected, the molecule displays a trans configuration about the central C11═N2 bond. Bond lengths and angles observed in the structure are in normal ranges and comparable with those of a related Schiff base compound (Elmah et al., 1999). The hydroxy group is involved as donor in a strong intramolecular O—H···N hydrogen bond (Table 1) and as acceptor in an weak intermolecular N—H···O hydrogen interaction (Fig. 2, Table 1).

Related literature top

For general background to the properties of Schiff base compounds, see: Weber et al. (2007); Chen et al. (2008); May et al. (2004). For the structure of a related compound, see: Elmah et al. (1999).

Experimental top

Benzene-1,2-diamine (0.59 g, 5 mmol) and 4-(diethylamino)-2-hydroxybenzaldehyde (0.965 g, 5 mmol) were dissolved in methanol (15 ml). The mixture was heated to reflux for 6 h, then cooled to room temperature, then the solution was filtered and dried (yield 84%). Crystals of the title compound suitable for X-ray diffraction analysis were grown by slow evaporation of an ethanol solution. Esi-MS: calcd for C₁₇H₂₁N₃O + H m/z 283.37, found 284.72.

Computing details top

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear (Rigaku, 2005); data reduction: CrystalClear (Rigaku, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick,2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound with the atomic numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. Packing diagram of the title compound, showing the structure along the a axis. Intermolecular N—H···O hydrogen bonds are shown as dashed lines.

2-[(E)-(2-Aminophenyl)iminomethyl]-5-(dimethylamino)phenol top

Crystal data top

C₁₇H₂₁N₃O	F(000) = 608
M_r = 283.37	D_x = 1.213 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 1474 reflections
a = 6.5904 (13) Å	θ = 3.1–27.8°
b = 12.703 (3) Å	µ = 0.08 mm⁻¹
c = 18.538 (4) Å	T = 293 K
V = 1552.0 (6) Å³	Prism, yellow
Z = 4	0.20 × 0.20 × 0.20 mm

Data collection top

Rigaku SCXmini diffractometer	3566 independent reflections
Radiation source: fine-focus sealed tube	1996 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.063
Detector resolution: 13.6612 pixels mm^-1	θ_max = 27.5°, θ_min = 3.2°
ω scans	h = −8→8
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −16→16
T_min = 0.973, T_max = 0.979	l = −24→24
16156 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)] = 0.058	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.176	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ²(F_o²) + (0.1P)²] where P = (F_o² + 2F_c²)/3
2061 reflections	(Δ/σ)_max = 0.001
194 parameters	Δρ_max = 0.13 e Å⁻³
0 restraints	Δρ_min = −0.14 e Å⁻³

Crystal data top

C₁₇H₂₁N₃O	V = 1552.0 (6) Å³
M_r = 283.37	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 6.5904 (13) Å	µ = 0.08 mm⁻¹
b = 12.703 (3) Å	T = 293 K
c = 18.538 (4) Å	0.20 × 0.20 × 0.20 mm

Data collection top

Rigaku SCXmini diffractometer	3566 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	1996 reflections with I > 2σ(I)
T_min = 0.973, T_max = 0.979	R_int = 0.063
16156 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.058	0 restraints
wR(F²) = 0.176	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 0.13 e Å⁻³
2061 reflections	Δρ_min = −0.14 e Å⁻³
194 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
C1	0.2951 (5)	0.8186 (2)	0.07623 (17)	0.0481 (8)
O1	−0.0143 (4)	0.8354 (2)	0.14362 (14)	0.0690 (8)
N2	0.3009 (5)	0.7252 (2)	0.18825 (15)	0.0600 (8)
C3	0.0114 (5)	0.9219 (3)	0.03213 (18)	0.0532 (8)
H3A	−0.1196	0.9471	0.0389	0.064*
C4	0.1183 (5)	0.9498 (2)	−0.03042 (18)	0.0528 (8)
C2	0.0966 (5)	0.8582 (3)	0.08329 (17)	0.0508 (8)
C11	0.3911 (6)	0.7562 (2)	0.13124 (19)	0.0569 (9)
H11A	0.5264	0.7374	0.1249	0.068*
C6	0.3994 (5)	0.8473 (2)	0.01367 (17)	0.0543 (8)
H6A	0.5309	0.8225	0.0072	0.065*
N1	0.0326 (4)	1.0119 (3)	−0.08228 (15)	0.0627 (8)
C5	0.3174 (5)	0.9101 (3)	−0.03833 (17)	0.0535 (8)
H5A	0.3928	0.9270	−0.0792	0.064*
C12	0.4162 (5)	0.6759 (3)	0.24289 (18)	0.0555 (9)
C9	0.1458 (6)	1.0453 (3)	−0.1467 (2)	0.0724 (11)
H9A	0.0496	1.0655	−0.1839	0.087*
H9B	0.2228	0.9858	−0.1648	0.087*
N3	0.1521 (5)	0.5451 (3)	0.25389 (18)	0.0844 (11)
H3B	0.1048	0.4891	0.2739	0.101*
H3C	0.0871	0.5743	0.2190	0.101*
C13	0.3329 (6)	0.5880 (3)	0.27784 (19)	0.0619 (10)
C14	0.4406 (7)	0.5432 (3)	0.3335 (2)	0.0773 (12)
H14A	0.3869	0.4849	0.3571	0.093*
C16	0.7079 (7)	0.6677 (3)	0.3207 (2)	0.0798 (12)
H16A	0.8329	0.6943	0.3352	0.096*
C17	0.6027 (6)	0.7135 (3)	0.2645 (2)	0.0660 (10)
H17A	0.6589	0.7710	0.2406	0.079*
C7	−0.1687 (6)	1.0581 (3)	−0.0710 (2)	0.0727 (11)
H7A	−0.2585	1.0041	−0.0522	0.087*
H7B	−0.2223	1.0804	−0.1173	0.087*
C10	0.2883 (6)	1.1352 (3)	−0.1340 (3)	0.0871 (13)
H10A	0.3566	1.1524	−0.1782	0.131*
H10B	0.3866	1.1155	−0.0982	0.131*
H10C	0.2133	1.1952	−0.1175	0.131*
C15	0.6240 (8)	0.5819 (4)	0.3550 (2)	0.0818 (13)
H15A	0.6929	0.5502	0.3930	0.098*
C8	−0.1708 (7)	1.1508 (4)	−0.0202 (3)	0.0933 (14)
H8A	−0.3070	1.1767	−0.0154	0.140*
H8B	−0.0854	1.2055	−0.0390	0.140*
H8C	−0.1213	1.1291	0.0262	0.140*
H1A	0.067 (7)	0.796 (4)	0.168 (2)	0.098 (16)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0444 (16)	0.0430 (16)	0.0570 (19)	0.0037 (14)	0.0031 (16)	−0.0112 (15)
O1	0.0518 (14)	0.0809 (18)	0.0742 (17)	0.0140 (14)	0.0173 (13)	0.0094 (15)
N2	0.0612 (17)	0.0546 (16)	0.0643 (18)	0.0097 (15)	0.0110 (15)	0.0026 (15)
C3	0.0384 (16)	0.0548 (19)	0.067 (2)	0.0022 (15)	0.0021 (16)	−0.0071 (17)
C4	0.0463 (17)	0.0486 (17)	0.064 (2)	−0.0065 (15)	−0.0084 (16)	−0.0116 (16)
C2	0.0469 (17)	0.0475 (17)	0.0581 (19)	−0.0039 (16)	0.0080 (17)	−0.0092 (16)
C11	0.056 (2)	0.0458 (18)	0.069 (2)	0.0095 (16)	0.0007 (19)	−0.0099 (17)
C6	0.0449 (16)	0.0517 (19)	0.066 (2)	0.0060 (16)	0.0064 (17)	−0.0112 (16)
N1	0.0488 (16)	0.0772 (19)	0.0622 (17)	0.0011 (15)	−0.0072 (15)	0.0005 (16)
C5	0.0438 (17)	0.0570 (18)	0.060 (2)	−0.0009 (16)	0.0015 (17)	−0.0088 (17)
C12	0.0560 (19)	0.0485 (18)	0.062 (2)	0.0119 (17)	0.0056 (18)	−0.0012 (17)
C9	0.068 (2)	0.080 (3)	0.069 (2)	0.004 (2)	−0.014 (2)	0.004 (2)
N3	0.077 (2)	0.084 (2)	0.093 (2)	−0.0138 (19)	0.008 (2)	0.012 (2)
C13	0.062 (2)	0.056 (2)	0.067 (2)	0.0106 (19)	0.010 (2)	−0.0010 (18)
C14	0.084 (3)	0.067 (2)	0.080 (3)	0.019 (2)	0.020 (2)	0.012 (2)
C16	0.066 (2)	0.083 (3)	0.090 (3)	0.019 (2)	−0.004 (2)	0.000 (3)
C17	0.063 (2)	0.059 (2)	0.076 (2)	0.010 (2)	0.005 (2)	0.0051 (19)
C7	0.051 (2)	0.088 (3)	0.079 (2)	0.002 (2)	−0.017 (2)	0.008 (2)
C10	0.075 (3)	0.083 (3)	0.102 (3)	−0.011 (3)	−0.016 (3)	0.014 (2)
C15	0.091 (3)	0.078 (3)	0.076 (3)	0.029 (3)	0.000 (3)	0.017 (2)
C8	0.076 (3)	0.098 (3)	0.106 (3)	0.024 (3)	−0.001 (3)	−0.005 (3)

Geometric parameters (Å, º) top

C1—C6	1.397 (4)	C9—H9B	0.9700
C1—C2	1.407 (4)	N3—C13	1.383 (5)
C1—C11	1.438 (4)	N3—H3B	0.8600
O1—C2	1.367 (4)	N3—H3C	0.8600
O1—H1A	0.86 (5)	C13—C14	1.376 (5)
N2—C11	1.275 (4)	C14—C15	1.365 (6)
N2—C12	1.413 (4)	C14—H14A	0.9300
C3—C2	1.367 (4)	C16—C15	1.377 (6)
C3—C4	1.402 (5)	C16—C17	1.380 (5)
C3—H3A	0.9300	C16—H16A	0.9300
C4—N1	1.366 (4)	C17—H17A	0.9300
C4—C5	1.413 (5)	C7—C8	1.509 (5)
C11—H11A	0.9300	C7—H7A	0.9700
C6—C5	1.363 (4)	C7—H7B	0.9700
C6—H6A	0.9300	C10—H10A	0.9600
N1—C7	1.465 (5)	C10—H10B	0.9600
N1—C9	1.471 (4)	C10—H10C	0.9600
C5—H5A	0.9300	C15—H15A	0.9300
C12—C17	1.378 (5)	C8—H8A	0.9600
C12—C13	1.403 (5)	C8—H8B	0.9600
C9—C10	1.497 (5)	C8—H8C	0.9600
C9—H9A	0.9700

C6—C1—C2	116.2 (3)	C13—N3—H3C	120.0
C6—C1—C11	121.1 (3)	H3B—N3—H3C	120.0
C2—C1—C11	122.7 (3)	C14—C13—N3	121.4 (4)
C2—O1—H1A	103 (3)	C14—C13—C12	118.3 (4)
C11—N2—C12	118.7 (3)	N3—C13—C12	120.2 (3)
C2—C3—C4	121.1 (3)	C15—C14—C13	121.8 (4)
C2—C3—H3A	119.4	C15—C14—H14A	119.1
C4—C3—H3A	119.4	C13—C14—H14A	119.1
N1—C4—C3	121.4 (3)	C15—C16—C17	118.7 (4)
N1—C4—C5	121.1 (3)	C15—C16—H16A	120.6
C3—C4—C5	117.5 (3)	C17—C16—H16A	120.6
O1—C2—C3	118.2 (3)	C12—C17—C16	121.4 (4)
O1—C2—C1	119.8 (3)	C12—C17—H17A	119.3
C3—C2—C1	121.9 (3)	C16—C17—H17A	119.3
N2—C11—C1	123.5 (3)	N1—C7—C8	114.2 (3)
N2—C11—H11A	118.2	N1—C7—H7A	108.7
C1—C11—H11A	118.2	C8—C7—H7A	108.7
C5—C6—C1	123.0 (3)	N1—C7—H7B	108.7
C5—C6—H6A	118.5	C8—C7—H7B	108.7
C1—C6—H6A	118.5	H7A—C7—H7B	107.6
C4—N1—C7	120.3 (3)	C9—C10—H10A	109.5
C4—N1—C9	121.9 (3)	C9—C10—H10B	109.5
C7—N1—C9	117.4 (3)	H10A—C10—H10B	109.5
C6—C5—C4	120.2 (3)	C9—C10—H10C	109.5
C6—C5—H5A	119.9	H10A—C10—H10C	109.5
C4—C5—H5A	119.9	H10B—C10—H10C	109.5
C17—C12—C13	119.4 (3)	C14—C15—C16	120.4 (4)
C17—C12—N2	122.3 (3)	C14—C15—H15A	119.8
C13—C12—N2	118.3 (3)	C16—C15—H15A	119.8
N1—C9—C10	114.2 (3)	C7—C8—H8A	109.5
N1—C9—H9A	108.7	C7—C8—H8B	109.5
C10—C9—H9A	108.7	H8A—C8—H8B	109.5
N1—C9—H9B	108.7	C7—C8—H8C	109.5
C10—C9—H9B	108.7	H8A—C8—H8C	109.5
H9A—C9—H9B	107.6	H8B—C8—H8C	109.5
C13—N3—H3B	120.0

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3B···O1ⁱ	0.86	2.55	3.395 (4)	167
O1—H1A···N2	0.86 (5)	1.82 (5)	2.638 (4)	157 (4)

Symmetry code: (i) −x, y−1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₇H₂₁N₃O
M_r	283.37
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	293
a, b, c (Å)	6.5904 (13), 12.703 (3), 18.538 (4)
V (Å³)	1552.0 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.20 × 0.20 × 0.20

Data collection
Diffractometer	Rigaku SCXmini diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku, 2005)
T_min, T_max	0.973, 0.979
No. of measured, independent and observed [I > 2σ(I)] reflections	16156, 3566, 1996
R_int	0.063
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.058, 0.176, 1.04
No. of reflections	2061
No. of parameters	194
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.13, −0.14

Computer programs: CrystalClear (Rigaku, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick,2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3B···O1ⁱ	0.86	2.55	3.395 (4)	167.3
O1—H1A···N2	0.86 (5)	1.82 (5)	2.638 (4)	157 (4)

Symmetry code: (i) −x, y−1/2, −z+1/2.

References

Chen, Z. H., Morimoto, H., Matsunaga, S. & Shibasaki, M. (2008). J. Am. Chem. Soc. 130, 2170–2171. Web of Science CSD CrossRef PubMed CAS Google Scholar
Elmah, A., Kabak, M. & Elerman, Y. (1999). J. Mol. Struct. 484, 229–234. Google Scholar
May, J. P., Ting, R., Lermer, L., Thomas, J. M., Roupioz, Y. & Perrin, D. M. (2004). J. Am. Chem. Soc. 126, 4145–4156. Web of Science CrossRef PubMed CAS Google Scholar
Rigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Weber, B., Tandon, R. & Himsl, D. (2007). Z. Anorg. Allg. Chem. 633, 1159–1162. Web of Science CSD CrossRef CAS Google Scholar

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