Crystal structure of (E)-5-di-ethyl-amino-2-({[4-(di-methyl-amino)-phen-yl]imino}-meth-yl)phenol.

The title Schiff base compound, C19H25N3O, is approximately planar, with a dihedral angle of 9.03 (13)° between the planes of the aromatic rings, and has an E conformation about the N=C bond. The mol-ecular structure is stabilized by an intra-molecular O-H⋯N hydrogen bond, with an S(6) ring motif. In the crystal, mol-ecules are linked by C-H⋯π inter-actions, forming sheets parallel to the bc plane.

Related literature

For biological activities of Schiff base derivatives, see: Savaliya et al. (2010 ▸); Xu et al. (2012 ▸). For the structures of similar compounds, see: Manvizhi et al. (2011 ▸); Thirugnanasundar et al. (2011 ▸).

Experimental

Crystal data

C19H25N3O

M = 311.42

Monoclinic,

a = 8.8201 (7) Å

b = 7.8850 (7) Å

c = 13.0639 (10) Å

β = 108.407 (3)°

V = 862.06 (12) Å3

Z = 2

Mo Kα radiation

μ = 0.08 mm−1

T = 295 K

0.26 × 0.22 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▸) T min = 0.981, T max = 0.985

13009 measured reflections

3825 independent reflections

2438 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.052

wR(F 2) = 0.159

S = 1.03

3825 reflections

214 parameters

6 restraints

H-atom parameters constrained

Δρmax = 0.29 e Å−3

Δρmin = −0.16 e Å−3

Data collection: APEX2 (Bruker, 2004 ▸); cell refinement: SAINT (Bruker, 2004 ▸); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▸); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▸); molecular graphics: PLATON (Spek, 2009 ▸) and Mercury (Macrae et al., 2008 ▸); software used to prepare material for publication: SHELXL97 and PLATON.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S2056989015011779/su5157sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015011779/su5157Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S2056989015011779/su5157Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S2056989015011779/su5157fig1.tif

The mol­ecular structure of the title compound, with atom labelling. Displacement ellipsoids are drawn at the 30% probability level. The intra­molecular O—H.·N hydrogen bonds is shown as a dashd lines (see Table 1 for details).

Click here for additional data file.

a . DOI: 10.1107/S2056989015011779/su5157fig2.tif

A view along the a axis of the crystal apcking of the title compound. The O—H.·N and C-H⋯π inter­actions are illustrated by dashed lines (see Table 1 for details).

CCDC reference: 1407678

Additional supporting information: crystallographic information; 3D view; checkCIF report

C19H25N3O	F(000) = 336
Mr = 311.42	Dx = 1.200 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 4428 reflections
a = 8.8201 (7) Å	θ = 2.4–27.2°
b = 7.8850 (7) Å	µ = 0.08 mm−1
c = 13.0639 (10) Å	T = 295 K
β = 108.407 (3)°	Block, colourless
V = 862.06 (12) Å3	0.26 × 0.22 × 0.20 mm
Z = 2

Bruker Kappa APEXII CCD diffractometer	3825 independent reflections
Radiation source: fine-focus sealed tube	2438 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.027
ω and φ scan	θmax = 27.3°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→10
Tmin = 0.981, Tmax = 0.985	k = −10→10
13009 measured reflections	l = −16→16

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.052	H-atom parameters constrained
wR(F2) = 0.159	w = 1/[σ2(Fo2) + (0.0751P)2 + 0.1538P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max < 0.001
3825 reflections	Δρmax = 0.29 e Å−3
214 parameters	Δρmin = −0.16 e Å−3
6 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.014 (4)

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.

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 > 2sigma(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	0.4431 (4)	0.6814 (5)	0.2015 (2)	0.0780 (10)
H1A	0.3484	0.6253	0.1573	0.117*
H1B	0.5213	0.6840	0.1644	0.117*
H1C	0.4171	0.7953	0.2159	0.117*
C2	0.6641 (4)	0.5264 (6)	0.3287 (3)	0.0902 (12)
H2A	0.7316	0.5867	0.3901	0.135*
H2B	0.7039	0.5405	0.2688	0.135*
H2C	0.6635	0.4081	0.3459	0.135*
C3	0.4220 (3)	0.5850 (3)	0.3736 (2)	0.0502 (6)
C4	0.2713 (3)	0.6598 (4)	0.3525 (2)	0.0547 (7)
H4	0.2275	0.7180	0.2880	0.066*
C5	0.1861 (3)	0.6502 (4)	0.42371 (19)	0.0512 (6)
H5	0.0860	0.7008	0.4067	0.061*
C6	0.2487 (3)	0.5648 (3)	0.52175 (18)	0.0444 (6)
C7	0.3965 (3)	0.4922 (3)	0.5425 (2)	0.0508 (6)
H7	0.4405	0.4352	0.6075	0.061*
C8	0.4820 (3)	0.5003 (4)	0.4715 (2)	0.0537 (7)
H8	0.5816	0.4483	0.4889	0.064*
C9	0.0435 (3)	0.6249 (4)	0.59847 (19)	0.0481 (6)
H9	−0.0034	0.6975	0.5411	0.058*
C10	−0.0294 (3)	0.6066 (3)	0.68154 (19)	0.0462 (6)
C11	−0.1669 (3)	0.6947 (3)	0.6784 (2)	0.0537 (7)
H11	−0.2150	0.7626	0.6188	0.064*
C12	−0.2347 (3)	0.6864 (4)	0.7586 (2)	0.0596 (8)
H12	−0.3278	0.7467	0.7524	0.072*
C13	−0.1648 (3)	0.5871 (4)	0.8507 (2)	0.0528 (6)
C14	−0.0279 (3)	0.4940 (3)	0.8547 (2)	0.0523 (7)
H14	0.0198	0.4255	0.9141	0.063*
C15	0.0370 (3)	0.5025 (3)	0.7722 (2)	0.0472 (6)
C16	−0.1784 (4)	0.4511 (5)	1.0194 (3)	0.0834 (10)
H16A	−0.2702	0.4176	1.0403	0.100*
H16B	−0.1393	0.3520	0.9915	0.100*
C17	−0.0541 (5)	0.5166 (6)	1.1125 (3)	0.1089 (14)
H17A	0.0389	0.5432	1.0925	0.163*
H17B	−0.0274	0.4327	1.1686	0.163*
H17C	−0.0917	0.6173	1.1380	0.163*
C18	−0.3507 (4)	0.7080 (5)	0.9409 (3)	0.0835 (10)
H18A	−0.3375	0.7326	1.0160	0.100*
H18B	−0.3372	0.8131	0.9062	0.100*
C19	−0.5106 (4)	0.6420 (8)	0.8890 (4)	0.1178 (15)
H19A	−0.5223	0.6129	0.8156	0.177*
H19B	−0.5881	0.7267	0.8905	0.177*
H19C	−0.5270	0.5428	0.9268	0.177*
N1	0.5063 (3)	0.5915 (4)	0.30117 (18)	0.0693 (7)
N2	0.1707 (2)	0.5451 (3)	0.60028 (16)	0.0495 (5)
N3	−0.2261 (3)	0.5836 (4)	0.9344 (2)	0.0826 (9)
O1	0.1678 (2)	0.4075 (3)	0.77919 (17)	0.0695 (6)
H1	0.2010	0.4308	0.7289	0.104*

	U11	U22	U33	U12	U13	U23
C1	0.097 (2)	0.090 (3)	0.0568 (17)	−0.0042 (19)	0.0384 (16)	0.0063 (17)
C2	0.0743 (17)	0.127 (3)	0.082 (2)	0.0100 (19)	0.0428 (18)	0.012 (2)
C3	0.0561 (14)	0.0511 (15)	0.0454 (13)	−0.0092 (13)	0.0189 (11)	0.0004 (12)
C4	0.0608 (16)	0.0587 (17)	0.0431 (13)	0.0034 (14)	0.0143 (12)	0.0113 (13)
C5	0.0487 (13)	0.0557 (16)	0.0487 (14)	0.0064 (12)	0.0148 (11)	0.0060 (13)
C6	0.0510 (14)	0.0410 (14)	0.0418 (13)	−0.0028 (12)	0.0154 (11)	0.0013 (11)
C7	0.0506 (14)	0.0535 (16)	0.0453 (14)	0.0033 (13)	0.0110 (11)	0.0073 (12)
C8	0.0494 (14)	0.0554 (16)	0.0544 (16)	0.0018 (12)	0.0137 (12)	0.0038 (13)
C9	0.0505 (14)	0.0473 (15)	0.0436 (13)	−0.0018 (13)	0.0107 (11)	0.0001 (11)
C10	0.0455 (13)	0.0444 (14)	0.0467 (13)	−0.0009 (11)	0.0116 (10)	−0.0012 (11)
C11	0.0547 (14)	0.0533 (16)	0.0496 (14)	0.0138 (12)	0.0113 (12)	0.0110 (12)
C12	0.0529 (14)	0.066 (2)	0.0604 (16)	0.0188 (13)	0.0188 (13)	0.0095 (14)
C13	0.0533 (14)	0.0548 (16)	0.0530 (14)	0.0039 (13)	0.0207 (11)	0.0075 (13)
C14	0.0543 (15)	0.0523 (16)	0.0506 (15)	0.0101 (13)	0.0167 (12)	0.0147 (13)
C15	0.0403 (12)	0.0443 (14)	0.0554 (15)	0.0053 (11)	0.0129 (11)	0.0050 (12)
C16	0.086 (2)	0.093 (3)	0.081 (2)	0.0042 (18)	0.0414 (19)	0.0168 (16)
C17	0.126 (3)	0.098 (3)	0.097 (3)	0.010 (3)	0.028 (3)	−0.008 (3)
C18	0.080 (2)	0.107 (3)	0.075 (2)	0.0190 (17)	0.0400 (18)	0.0039 (19)
C19	0.094 (3)	0.134 (4)	0.131 (4)	0.014 (3)	0.043 (3)	−0.015 (3)
N1	0.0737 (14)	0.083 (2)	0.0611 (15)	0.0044 (13)	0.0357 (13)	0.0146 (14)
N2	0.0530 (12)	0.0515 (14)	0.0459 (11)	0.0007 (10)	0.0184 (9)	0.0030 (10)
N3	0.0769 (16)	0.112 (2)	0.0696 (16)	0.0288 (15)	0.0381 (13)	0.0210 (15)
O1	0.0666 (12)	0.0777 (14)	0.0737 (14)	0.0302 (11)	0.0356 (10)	0.0283 (11)

C1—N1	1.432 (4)	C11—C12	1.363 (4)
C1—H1A	0.9600	C11—H11	0.9300
C1—H1B	0.9600	C12—C13	1.404 (4)
C1—H1C	0.9600	C12—H12	0.9300
C2—N1	1.419 (4)	C13—N3	1.364 (3)
C2—H2A	0.9600	C13—C14	1.400 (3)
C2—H2B	0.9600	C14—C15	1.373 (4)
C2—H2C	0.9600	C14—H14	0.9300
C3—N1	1.377 (3)	C15—O1	1.354 (3)
C3—C8	1.390 (4)	C16—C17	1.451 (5)
C3—C4	1.400 (4)	C16—N3	1.485 (4)
C4—C5	1.370 (4)	C16—H16A	0.9700
C4—H4	0.9300	C16—H16B	0.9700
C5—C6	1.397 (3)	C17—H17A	0.9600
C5—H5	0.9300	C17—H17B	0.9600
C6—C7	1.370 (3)	C17—H17C	0.9600
C6—N2	1.413 (3)	C18—C19	1.454 (5)
C7—C8	1.370 (4)	C18—N3	1.495 (4)
C7—H7	0.9300	C18—H18A	0.9700
C8—H8	0.9300	C18—H18B	0.9700
C9—N2	1.280 (3)	C19—H19A	0.9600
C9—C10	1.433 (3)	C19—H19B	0.9600
C9—H9	0.9300	C19—H19C	0.9600
C10—C11	1.386 (3)	O1—H1	0.8200
C10—C15	1.407 (3)
N1—C1—H1A	109.5	N3—C13—C14	121.0 (2)
N1—C1—H1B	109.5	N3—C13—C12	121.3 (2)
H1A—C1—H1B	109.5	C14—C13—C12	117.7 (2)
N1—C1—H1C	109.5	C15—C14—C13	120.9 (2)
H1A—C1—H1C	109.5	C15—C14—H14	119.5
H1B—C1—H1C	109.5	C13—C14—H14	119.5
N1—C2—H2A	109.5	O1—C15—C14	118.5 (2)
N1—C2—H2B	109.5	O1—C15—C10	119.9 (2)
H2A—C2—H2B	109.5	C14—C15—C10	121.6 (2)
N1—C2—H2C	109.5	C17—C16—N3	109.7 (3)
H2A—C2—H2C	109.5	C17—C16—H16A	109.7
H2B—C2—H2C	109.5	N3—C16—H16A	109.7
N1—C3—C8	121.2 (2)	C17—C16—H16B	109.7
N1—C3—C4	122.3 (2)	N3—C16—H16B	109.7
C8—C3—C4	116.4 (2)	H16A—C16—H16B	108.2
C5—C4—C3	122.2 (2)	C16—C17—H17A	109.5
C5—C4—H4	118.9	C16—C17—H17B	109.5
C3—C4—H4	118.9	H17A—C17—H17B	109.5
C4—C5—C6	120.4 (2)	C16—C17—H17C	109.5
C4—C5—H5	119.8	H17A—C17—H17C	109.5
C6—C5—H5	119.8	H17B—C17—H17C	109.5
C7—C6—C5	117.3 (2)	C19—C18—N3	111.1 (3)
C7—C6—N2	117.5 (2)	C19—C18—H18A	109.4
C5—C6—N2	125.2 (2)	N3—C18—H18A	109.4
C8—C7—C6	122.6 (2)	C19—C18—H18B	109.4
C8—C7—H7	118.7	N3—C18—H18B	109.4
C6—C7—H7	118.7	H18A—C18—H18B	108.0
C7—C8—C3	121.0 (2)	C18—C19—H19A	109.5
C7—C8—H8	119.5	C18—C19—H19B	109.5
C3—C8—H8	119.5	H19A—C19—H19B	109.5
N2—C9—C10	122.5 (2)	C18—C19—H19C	109.5
N2—C9—H9	118.8	H19A—C19—H19C	109.5
C10—C9—H9	118.8	H19B—C19—H19C	109.5
C11—C10—C15	116.4 (2)	C3—N1—C2	120.8 (2)
C11—C10—C9	121.6 (2)	C3—N1—C1	120.2 (2)
C15—C10—C9	121.9 (2)	C2—N1—C1	118.6 (2)
C12—C11—C10	123.1 (2)	C9—N2—C6	123.9 (2)
C12—C11—H11	118.5	C13—N3—C16	121.5 (3)
C10—C11—H11	118.5	C13—N3—C18	121.1 (3)
C11—C12—C13	120.3 (2)	C16—N3—C18	117.4 (2)
C11—C12—H12	119.8	C15—O1—H1	109.5
C13—C12—H12	119.8
N1—C3—C4—C5	178.6 (3)	C13—C14—C15—C10	1.1 (4)
C8—C3—C4—C5	−0.3 (4)	C11—C10—C15—O1	177.5 (3)
C3—C4—C5—C6	0.5 (4)	C9—C10—C15—O1	−4.4 (4)
C4—C5—C6—C7	−0.2 (4)	C11—C10—C15—C14	−2.3 (4)
C4—C5—C6—N2	−179.1 (3)	C9—C10—C15—C14	175.8 (3)
C5—C6—C7—C8	−0.3 (4)	C8—C3—N1—C2	−6.4 (5)
N2—C6—C7—C8	178.7 (2)	C4—C3—N1—C2	174.8 (3)
C6—C7—C8—C3	0.5 (4)	C8—C3—N1—C1	−179.2 (3)
N1—C3—C8—C7	−179.0 (3)	C4—C3—N1—C1	2.1 (4)
C4—C3—C8—C7	−0.2 (4)	C10—C9—N2—C6	−177.7 (2)
N2—C9—C10—C11	179.7 (2)	C7—C6—N2—C9	170.0 (2)
N2—C9—C10—C15	1.7 (4)	C5—C6—N2—C9	−11.0 (4)
C15—C10—C11—C12	1.4 (4)	C14—C13—N3—C16	−15.8 (5)
C9—C10—C11—C12	−176.7 (3)	C12—C13—N3—C16	165.5 (3)
C10—C11—C12—C13	0.8 (4)	C14—C13—N3—C18	167.5 (3)
C11—C12—C13—N3	176.7 (3)	C12—C13—N3—C18	−11.3 (5)
C11—C12—C13—C14	−2.1 (4)	C17—C16—N3—C13	97.4 (4)
N3—C13—C14—C15	−177.6 (3)	C17—C16—N3—C18	−85.7 (4)
C12—C13—C14—C15	1.2 (4)	C19—C18—N3—C13	91.4 (4)
C13—C14—C15—O1	−178.8 (3)	C19—C18—N3—C16	−85.5 (4)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N2	0.82	1.85	2.585 (3)	148
C11—H11···Cg1i	0.93	2.71	3.517 (3)	145
C17—H17B···Cg2ii	0.96	2.90	3.743 (5)	147

Table 1

Hydrogen-bond geometry (, )

Cg1 and Cg2 are the centroids of rings C3C8 and C10C15, respectively.

DHA	DH	HA	D A	DHA
O1H1N2	0.82	1.85	2.585(3)	148
C11H11Cg1i	0.93	2.71	3.517(3)	145
C17H17B Cg2ii	0.96	2.90	3.743(5)	147

Symmetry codes: (i) ; (ii) .