Crystal structure of (E)-5-di­ethyl­amino-2-({[4-(di­methyl­amino)­phen­yl]imino}­meth­yl)phenol

Rani, C.V.; Chakkaravarthi, G.; Rajagopal, G.

doi:10.1107/S2056989015011779

organic compounds

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Volume 71| Part 7| July 2015| Page o503

doi:10.1107/S2056989015011779

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Crystal structure of (E)-5-diethylamino-2-({[4-(dimethylamino)phenyl]imino}methyl)phenol

C. Vidya Rani,^a G. Chakkaravarthi ^b ^* and G. Rajagopal ^a ^*

^aPG & Research Department of Chemistry, Chikkanna Government Arts College, Tiruppur 641 602, India, and ^bDepartment of Physics, CPCL Polytechnic College, Chennai 600 068, India
^*Correspondence e-mail: chakkaravarthi_2005@yahoo.com, rajagopal18@yahoo.com

Edited by H. Stoeckli-Evans, University of Neuchâtel, Switzerland (Received 15 June 2015; accepted 19 June 2015; online 24 June 2015)

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 molecular structure is stabilized by an intramolecular O—H⋯N hydrogen bond, with an S(6) ring motif. In the crystal, molecules are linked by C—H⋯π interactions, forming sheets parallel to the bc plane.

Keywords: crystal structure; Schiff base; intramolecular O—H⋯N hydrogen bond; C—H⋯π interactions.

CCDC reference: 1407678

1. 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 ).

2. Experimental

2.1. Crystal data

C₁₉H₂₅N₃O
M_r = 311.42
Monoclinic, P 2₁
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

2.2. 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

2.3. Refinement

R[F² > 2σ(F²)] = 0.052
wR(F²) = 0.159
S = 1.03
3825 reflections
214 parameters
6 restraints
H-atom parameters constrained
Δρ_max = 0.29 e Å⁻³
Δρ_min = −0.16 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of rings C3–C8 and C10–C15, respectively.

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
Symmetry codes: (i) $[-x, y+{\script{1\over 2}}, -z+1]$ ; (ii) $[-x, y-{\script{1\over 2}}, -z+2]$ .

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.

Supporting information

CCDC reference: 1407678

Crystal structure: contains datablocks global, I. DOI: 10.1107/S2056989015011779/su5157sup1.cif

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

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

checkCIF report

Structural commentary top

Schiff base derivatives are known to exhibit antimicrobial (Savaliya et al., 2010) and antibacterial (Xu et al., 2012) activities. Herein we report on the synthesis and the crystal structure of a new Schiff base compound.

The molecular structure of the title compound is illustrated in Fg. 1. The geometric parameters are comparable to those reported for similar structures (Manvizhi et al., 2011; Thirugnanasundar et al., 2011). The dihedral angle between the benzene rings (C3—C8) and (C10—C15) is 9.03 (13)°. The molecular structure is stabilized by an intramolecular O—H···N hydrogen bond (Table 1 and Fig. 1).

In the crystal, molecules are linked by C—H···π interactions forming sheets parallel to the bc plane (Table 1 and Fig. 2).

Synthesis and crystallization top

To an ethanol solution (10 ml) of 5-(diethylamino)-2-hydroxybenzaldehyde (96.5 mg, 0.5 mol) was added N¹,N¹-dimethylbenzene-1,4-diamine (68 mg, 0.5 mol). The mixture was stirred and 2 to 3 drops of glacial acetic acid were added. Stirring was continued for 30 mins and then the reaction mixture was refluxed for 2 h. On completion of the reaction, monitored by TLC, the mixture was allowed to cool to room temperature and the solid yellow precipitate that formed was filtered, dried, and recrystallized from DMF, giving colourless block-like crystals.

Refinement top

Crystal data, data collection and structure refinement details are summarized in Table 2. H atoms were positioned geometrically and refined using riding model: O—H = 0.82 Å, C—H = 0.93 - 0.97 Å with U_iso(H) = 1.5Ueq(O,C) for the hydroxyl and methyl H atoms and 1.2U_eq(C) for other H atoms. The components of the anisotropic displacement parameters of the atoms in bonds N3—C16, N3—C18 and N1—C2 were restrained to be equal within an effective standard deviation of 0.001 using the DELU command, and the C16—C17 bond distance was restrained to 1.54 (1) Å.

Related literature top

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).

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); 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 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. 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).
	Fig. 2. 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).

(E)-5-Diethylamino-2-({[4-(dimethylamino)phenyl]imino}methyl)phenol top

Crystal data top

C₁₉H₂₅N₃O	F(000) = 336
M_r = 311.42	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0751P)² + 0.1538P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max < 0.001
3825 reflections	Δρ_max = 0.29 e Å⁻³
214 parameters	Δρ_min = −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)

Crystal data top

C₁₉H₂₅N₃O	V = 862.06 (12) Å³
M_r = 311.42	Z = 2
Monoclinic, P2₁	Mo Kα radiation
a = 8.8201 (7) Å	µ = 0.08 mm⁻¹
b = 7.8850 (7) Å	T = 295 K
c = 13.0639 (10) Å	0.26 × 0.22 × 0.20 mm
β = 108.407 (3)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	3825 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2438 reflections with I > 2σ(I)
T_min = 0.981, T_max = 0.985	R_int = 0.027
13009 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.052	6 restraints
wR(F²) = 0.159	H-atom parameters constrained
S = 1.03	Δρ_max = 0.29 e Å⁻³
3825 reflections	Δρ_min = −0.16 e Å⁻³
214 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of rings C3-C8 and C10-C15, respectively.

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

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

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of rings C3-C8 and C10-C15, respectively.

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

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

Acknowledgements

The authors acknowledge the SAIF, IIT, Madras, for the data collection.

References

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Crystal structure of (E)-5-di­ethyl­amino-2-({[4-(di­methyl­amino)­phen­yl]imino}­meth­yl)phenol

1. Related literature

2. Experimental

2.1. Crystal data

2.2. Data collection

2.3. Refinement

Supporting information

Acknowledgements

References

organic compounds

Crystal structure of (E)-5-diethylamino-2-({[4-(dimethylamino)phenyl]imino}methyl)phenol