2-[(E)-(2-Amino-phen-yl)imino-meth-yl]-5-(dimethyl-amino)phenol.

The mol-ecule of the title compound, C(17)H(21)N(3)O, 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 intra-molecular O-H⋯N hydrogen bond is present. An inter-molecular N-H⋯O hydrogen-bonding inter-action 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 = 283.37

Orthorhombic,

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[F 2 > 2σ(F 2)] = 0.058

wR(F 2) = 0.176

S = 1.04

2061 reflections

194 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.13 e Å−3

Δρmin = −0.14 e Å−3

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.

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

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

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

C17H21N3O	F(000) = 608
Mr = 283.37	Dx = 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

Rigaku SCXmini diffractometer	3566 independent reflections
Radiation source: fine-focus sealed tube	1996 reflections with I > 2σ(I)
graphite	Rint = 0.063
Detector resolution: 13.6612 pixels mm-1	θmax = 27.5°, θmin = 3.2°
ω scans	h = −8→8
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −16→16
Tmin = 0.973, Tmax = 0.979	l = −24→24
16156 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)] = 0.058	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(Fo2) + (0.1P)2] where P = (Fo2 + 2Fc2)/3
2061 reflections	(Δ/σ)max = 0.001
194 parameters	Δρmax = 0.13 e Å−3
0 restraints	Δρmin = −0.13 e Å−3

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.

	x	y	z	Uiso*/Ueq
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)*

	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)

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

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)

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) .