Crystal structure of (E,E)-2′,4′-di­hydroxy­aceto­phenone azine di­methyl­formamide disolvate

Wen-Juan Li; Hong-Fei Han

doi:10.1107/S2056989016003686

. 2016 Mar 8;72(Pt 4):467–469. doi: 10.1107/S2056989016003686

Crystal structure of (E,E)-2′,4′-dihydroxyacetophenone azine dimethylformamide disolvate

Wen-Juan Li ^a, Hong-Fei Han ^a,^*

PMCID: PMC4910326 PMID: 27375866

The approximately planar (E,E)-2′,4′-dihydroxyacetophenone azine molecule is located on an inversion centre and linked with dimethylformamide solvent molecules via O—H⋯O hydrogen bonds.

Keywords: crystal structure; hydrogen bond; (E,E)-2′,4′-dihydroxyacetophenone azine

Abstract

In the title compound {systematic name: 4,4′-[1,1′-(hydrazinediylidene)bis(ethan-1-yl-1-ylidene)]bis(benzene-1,3-diol)}, C₁₆H₁₆N₂O₄·2C₃H₇NO, the (E,E)-2′,4′-dihydroxyacetophenone azine molecule is centrosymmetric, the mid-point of the N—N bond being located on an inversion centre. All the non-H atoms of the azine molecule are approximately coplanar, the maximum deviation being 0.017 (2) Å. An intramolecular O—H⋯N hydrogen bond occurs between the azine N atom and the hydroxy group. In the crystal, azine and dimethylformamide solvent molecules are linked by O—H⋯O hydrogen bonds.

Chemical context

Hydrazones are important compounds due to their possible applications in material and coordination chemistry. Fluorescence properties of hydrazones have been reported (Qin et al., 2009 ▸). Many organometallic compounds containing acylhydrazone ligands have also been synthesized for their potential magneto-chemical properties (Guo et al., 2010 ▸). In particular, they have received increasing interest for their biological activity as antioxidants (Kitaev et al., 1970 ▸), and their antimicrobial (Ramamohan et al., 1995 ▸) and antiviral properties (El-Tabl et al., 2008 ▸; Rollas & Küçükgüzel, 2007 ▸).

Although 2′,4′-dihydroxyacetophenone azine has been prepared and studied as a fluorescent probe, its structure has not been reported. As a part of our studies on synthesis and structural peculiarities of Schiff base ligands derived from 2′,4′-dihydroxyacetophenone and hydrazine, we determined the structure of the title compound, (E,E)-2′,4′-dihydroxyacetophenone azine dimethylformamide disolvate, (I).

Structural commentary

The molecular structure of the title compound is depicted in Fig. 1 ▸. The asymmetric unit contains one half-molecule of (E,E)-2′,4′-dihydroxyacetophenone azine and one dimethylformamide (DMF) molecule. The complete azine molecule is centrosymmetric and exists in an E,E configuration with respect to the two C=N bonds. The N1—C2 bond length of 1.301 (3) Å shows double-bond character. The C—O bond lengths [1.349 (3) and 1.358 (3) Å] are comparable with similar bonds in related structures (Chantrapromma et al., 2011 ▸; Tai et al., 2008 ▸). All the non-H atoms of the azine molecule are approximately coplanar. The nine atoms (i.e. N1, C1 and C2, and the six C atoms in the benzene ring) are essentially planar, with a mean deviation of 0.0024 Å. Each hydroxy group is nearly coplanar with its attached benzene ring; the r.m.s. deviation is 0.0045 Å for the seven non-H atoms. Intramolecular O—H⋯N hydrogen bonds exist in the azine molecule (Table 1 ▸).

The molecular structure of the title compound, showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. Only one DMF solvent molecule is shown. [Symmetry code: (i) −x + 1, −y + 1, −z + 1.]

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.82	1.82	2.543 (2)	147
O2—H2⋯O3ⁱ	0.82	1.84	2.649 (3)	171

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Symmetry code: (i) Inline graphic .

Supramolecular features

In the crystal of (I), intermolecular O—H⋯O hydrogen bonds exist between azine molecules and DMF molecules (Table 1 ▸ and Fig. 2 ▸).

The crystal packing of the title compound. Hydrogen bonds are shown as dashed lines. [Symmetry codes: (i) −x + 1, −y + 1, −z + 1; (ii) x − 1, y + 1, z.]

Database survey

A search of Cambridge Structural Database (Groom & Allen, 2014 ▸) for acetophenone azine gave 105 hits (excluding organometallics). There are four reported crystal structures of acetophenone azine containing hydroxy groups at the 2-position of benzene rings: (E,E)-2,2′-(1,1′-azinodiethylidyne)diphenol (Tai et al., 2008 ▸), (E,E)-4,4′-dichloro-2,2′-(1,1′-azinodiethylidyne)diphenol (Chang et al., 2007 ▸), (E,E)-3,3′-diethoxy-2,2′-(1,1′-azinodiethylidyne)diphenol (Fayos et al., 1980 ▸) and (E,E)-4,4′-dimethoxy-2,2′-(1,1′-azinodiethylidyne)diphenol (Zhang et al., 2008 ▸).

Synthesis and crystallization

A mixture of 2′,4′-dihydroxyacetophenone (3.06 g, 20 mmol), hydrazine sulfate (1.28 g, 10 mmol) and triethylamine (3.03 g, 30 mmol) in ethanol (40 ml) was heated under reflux for 24 h. After cooling, the precipitate was filtrated and washed with water to afford a yellow solid. Crystals of the title compound suitable for X-ray diffraction were obtained by slow evaporation of a solution of the solid in DMF at room temperature for 5 d (yield 1.20 g, 75%; m.p: 484–485 K). ¹H NMR (300 MHz, CDCl₃): δ 13.59 (s, 2H, OH), 10.14 (s, 2H, OH), 7.58–7.61 (d, 2H, ArH), 6.37–6.41 (d, 2H, ArH), 6.30–6.31 (s, 2H, ArH), 3.34 (d, 6H, CH₃).

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2 ▸. H atoms were placed geometrically (C—H = 0.93–0.96 Å and O—H = 0.82 Å) and refined as riding, with U _iso(H) = 1.2U _eq(C) for aromatic H atoms or 1.5U _eq(C,O) for methyl and hydroxy groups.

Table 2. Experimental details.

Crystal data
Chemical formula	C₁₆H₁₆N₂O₄·2C₃H₇NO
M _r	446.50
Crystal system, space group	Triclinic, P
Temperature (K)	298
a, b, c (Å)	6.1616 (7), 7.3109 (8), 13.4537 (15)
α, β, γ (°)	96.771 (1), 103.049 (2), 96.607 (1)
V (Å³)	579.96 (11)
Z	1
Radiation type	Mo Kα
μ (mm⁻¹)	0.09
Crystal size (mm)	0.48 × 0.43 × 0.21

Data collection
Diffractometer	Bruker SMART CCD area-detector
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996 ▸)
T _min, T _max	0.956, 0.981
No. of measured, independent and observed [I > 2σ(I)] reflections	2902, 2001, 1313
R _int	0.026
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F ² > 2σ(F ²)], wR(F ²), S	0.055, 0.187, 1.02
No. of reflections	2001
No. of parameters	149
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.28, −0.25

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Computer programs: SMART and SAINT (Bruker, 2007 ▸), SHELXS97, SHELXL97 and SHELXTL (Sheldrick, 2008 ▸).

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S2056989016003686/xu5885sup1.cif

e-72-00467-sup1.cif^{(16.2KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989016003686/xu5885Isup2.hkl

e-72-00467-Isup2.hkl^{(99KB, hkl)}

Click here for additional data file.^{(7.4KB, cml)}

Supporting information file. DOI: 10.1107/S2056989016003686/xu5885Isup3.cml

CCDC reference: 1457201

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

Acknowledgments

Financial support from the Natural Science Foundation of Shanxi Province (No. 2013011011-4) is gratefully acknowledged.

supplementary crystallographic information

Crystal data

C₁₆H₁₆N₂O₄·2C₃H₇NO	Z = 1
M_r = 446.50	F(000) = 238
Triclinic, P1	D_x = 1.278 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.1616 (7) Å	Cell parameters from 1119 reflections
b = 7.3109 (8) Å	θ = 3.0–26.5°
c = 13.4537 (15) Å	µ = 0.09 mm⁻¹
α = 96.771 (1)°	T = 298 K
β = 103.049 (2)°	Block, colorless
γ = 96.607 (1)°	0.48 × 0.43 × 0.21 mm
V = 579.96 (11) Å³

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Data collection

Bruker SMART CCD area-detector diffractometer	2001 independent reflections
Radiation source: fine-focus sealed tube	1313 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.026
phi and ω scans	θ_max = 25.0°, θ_min = 3.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −6→7
T_min = 0.956, T_max = 0.981	k = −8→7
2902 measured reflections	l = −15→15

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Refinement

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)] = 0.055	H-atom parameters constrained
wR(F²) = 0.187	w = 1/[σ²(F_o²) + (0.1079P)² + 0.0859P] where P = (F_o² + 2F_c²)/3
S = 1.02	(Δ/σ)_max < 0.001
2001 reflections	Δρ_max = 0.28 e Å⁻³
149 parameters	Δρ_min = −0.25 e Å⁻³
0 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: 0.17 (2)

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Special details

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.

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

	x	y	z	U_iso*/U_eq
N1	0.4279 (3)	0.5237 (2)	0.53085 (13)	0.0391 (5)
N2	0.5727 (4)	0.1587 (3)	0.91556 (16)	0.0566 (6)
O1	0.2575 (3)	0.7659 (2)	0.62846 (12)	0.0537 (5)
H1	0.3372	0.7270	0.5919	0.081*
O2	−0.2843 (3)	0.5582 (3)	0.80524 (14)	0.0679 (6)
H2	−0.2793	0.6712	0.8190	0.102*
O3	0.7469 (4)	−0.0813 (3)	0.87057 (18)	0.0899 (8)
C1	0.3219 (5)	0.1857 (3)	0.5203 (2)	0.0574 (7)
H1A	0.2229	0.1462	0.4531	0.086*
H1B	0.2779	0.1098	0.5681	0.086*
H1C	0.4737	0.1732	0.5172	0.086*
C2	0.3080 (3)	0.3858 (3)	0.55569 (15)	0.0374 (6)
C3	0.1542 (3)	0.4334 (3)	0.62014 (15)	0.0368 (6)
C4	0.1368 (4)	0.6208 (3)	0.65420 (16)	0.0403 (6)
C5	−0.0090 (4)	0.6624 (3)	0.71594 (16)	0.0458 (6)
H5	−0.0180	0.7861	0.7380	0.055*
C6	−0.1404 (4)	0.5221 (4)	0.74482 (17)	0.0479 (6)
C7	−0.1270 (4)	0.3382 (4)	0.71238 (18)	0.0528 (7)
H7	−0.2153	0.2431	0.7316	0.063*
C8	0.0176 (4)	0.2968 (3)	0.65154 (17)	0.0472 (6)
H8	0.0249	0.1723	0.6304	0.057*
C9	0.5795 (5)	−0.0016 (5)	0.8617 (2)	0.0696 (9)
H9	0.4489	−0.0589	0.8136	0.084*
C10	0.7669 (5)	0.2551 (5)	0.9909 (2)	0.0808 (9)
H10A	0.8729	0.1706	1.0084	0.121*
H10B	0.7228	0.3039	1.0516	0.121*
H10C	0.8355	0.3556	0.9632	0.121*
C11	0.3699 (5)	0.2460 (5)	0.8988 (3)	0.0889 (10)
H11A	0.2480	0.1611	0.8530	0.133*
H11B	0.3951	0.3568	0.8687	0.133*
H11C	0.3324	0.2778	0.9635	0.133*

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Atomic displacement parameters (Å²)

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0427 (11)	0.0333 (11)	0.0416 (10)	0.0063 (8)	0.0117 (8)	0.0035 (8)
N2	0.0545 (13)	0.0620 (15)	0.0553 (12)	0.0128 (11)	0.0150 (10)	0.0088 (11)
O1	0.0704 (11)	0.0331 (10)	0.0647 (11)	0.0015 (8)	0.0367 (9)	0.0024 (7)
O2	0.0738 (13)	0.0718 (14)	0.0713 (12)	0.0124 (10)	0.0428 (10)	0.0122 (10)
O3	0.0897 (16)	0.0827 (17)	0.1017 (17)	0.0266 (14)	0.0354 (13)	−0.0059 (13)
C1	0.0708 (17)	0.0345 (14)	0.0745 (17)	0.0076 (12)	0.0332 (14)	0.0080 (12)
C2	0.0380 (12)	0.0337 (12)	0.0377 (11)	0.0037 (9)	0.0037 (9)	0.0065 (9)
C3	0.0383 (12)	0.0346 (12)	0.0351 (11)	0.0028 (9)	0.0048 (9)	0.0057 (9)
C4	0.0450 (13)	0.0378 (13)	0.0364 (11)	0.0024 (10)	0.0078 (10)	0.0064 (9)
C5	0.0532 (14)	0.0414 (14)	0.0427 (12)	0.0066 (11)	0.0136 (11)	0.0020 (10)
C6	0.0451 (13)	0.0583 (16)	0.0411 (12)	0.0065 (11)	0.0120 (10)	0.0081 (11)
C7	0.0548 (15)	0.0502 (16)	0.0561 (15)	−0.0022 (12)	0.0199 (12)	0.0155 (11)
C8	0.0539 (14)	0.0385 (14)	0.0497 (13)	0.0031 (11)	0.0137 (11)	0.0102 (10)
C9	0.0675 (19)	0.081 (2)	0.0575 (16)	−0.0021 (16)	0.0183 (14)	0.0061 (15)
C10	0.078 (2)	0.075 (2)	0.078 (2)	0.0069 (17)	0.0043 (17)	0.0000 (16)
C11	0.069 (2)	0.102 (3)	0.102 (2)	0.0268 (19)	0.0191 (18)	0.032 (2)

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Geometric parameters (Å, º)

N1—C2	1.301 (3)	C3—C4	1.417 (3)
N1—N1ⁱ	1.391 (3)	C4—C5	1.389 (3)
N2—C9	1.313 (4)	C5—C6	1.380 (3)
N2—C10	1.430 (4)	C5—H5	0.9300
N2—C11	1.453 (3)	C6—C7	1.381 (3)
O1—C4	1.349 (3)	C7—C8	1.374 (3)
O1—H1	0.8200	C7—H7	0.9300
O2—C6	1.358 (3)	C8—H8	0.9300
O2—H2	0.8200	C9—H9	0.9300
O3—C9	1.232 (3)	C10—H10A	0.9600
C1—C2	1.503 (3)	C10—H10B	0.9600
C1—H1A	0.9600	C10—H10C	0.9600
C1—H1B	0.9600	C11—H11A	0.9600
C1—H1C	0.9600	C11—H11B	0.9600
C2—C3	1.465 (3)	C11—H11C	0.9600
C3—C8	1.396 (3)

C2—N1—N1ⁱ	116.3 (2)	O2—C6—C5	122.1 (2)
C9—N2—C10	120.9 (2)	O2—C6—C7	118.0 (2)
C9—N2—C11	121.2 (3)	C5—C6—C7	119.9 (2)
C10—N2—C11	117.9 (3)	C8—C7—C6	119.6 (2)
C4—O1—H1	109.5	C8—C7—H7	120.2
C6—O2—H2	109.5	C6—C7—H7	120.2
C2—C1—H1A	109.5	C7—C8—C3	122.9 (2)
C2—C1—H1B	109.5	C7—C8—H8	118.6
H1A—C1—H1B	109.5	C3—C8—H8	118.6
C2—C1—H1C	109.5	O3—C9—N2	124.5 (3)
H1A—C1—H1C	109.5	O3—C9—H9	117.8
H1B—C1—H1C	109.5	N2—C9—H9	117.8
N1—C2—C3	116.96 (19)	N2—C10—H10A	109.5
N1—C2—C1	122.62 (19)	N2—C10—H10B	109.5
C3—C2—C1	120.4 (2)	H10A—C10—H10B	109.5
C8—C3—C4	116.5 (2)	N2—C10—H10C	109.5
C8—C3—C2	121.9 (2)	H10A—C10—H10C	109.5
C4—C3—C2	121.6 (2)	H10B—C10—H10C	109.5
O1—C4—C5	117.0 (2)	N2—C11—H11A	109.5
O1—C4—C3	122.42 (19)	N2—C11—H11B	109.5
C5—C4—C3	120.6 (2)	H11A—C11—H11B	109.5
C6—C5—C4	120.7 (2)	N2—C11—H11C	109.5
C6—C5—H5	119.7	H11A—C11—H11C	109.5
C4—C5—H5	119.7	H11B—C11—H11C	109.5

N1ⁱ—N1—C2—C3	−179.63 (19)	C3—C4—C5—C6	−0.3 (3)
N1ⁱ—N1—C2—C1	−0.1 (3)	C4—C5—C6—O2	179.9 (2)
N1—C2—C3—C8	−179.94 (18)	C4—C5—C6—C7	0.2 (3)
C1—C2—C3—C8	0.5 (3)	O2—C6—C7—C8	−179.7 (2)
N1—C2—C3—C4	−0.2 (3)	C5—C6—C7—C8	0.0 (4)
C1—C2—C3—C4	−179.69 (19)	C6—C7—C8—C3	−0.1 (4)
C8—C3—C4—O1	−179.28 (19)	C4—C3—C8—C7	−0.1 (3)
C2—C3—C4—O1	0.9 (3)	C2—C3—C8—C7	179.7 (2)
C8—C3—C4—C5	0.3 (3)	C10—N2—C9—O3	0.1 (4)
C2—C3—C4—C5	−179.47 (19)	C11—N2—C9—O3	178.5 (3)
O1—C4—C5—C6	179.3 (2)

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Symmetry code: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.82	2.543 (2)	147
O2—H2···O3ⁱⁱ	0.82	1.84	2.649 (3)	171

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Symmetry code: (ii) x−1, y+1, z.

References

Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Chang, J.-G., He, G.-F. & Li, Y.-F. (2007). Acta Cryst. E63, o3982.
Chantrapromma, S., Jansrisewangwong, P., Chanawanno, K. & Fun, H.-K. (2011). Acta Cryst. E67, o2221–o2222. [DOI] [PMC free article] [PubMed]
El-Tabl, A. S., El-Saied, F. A., Plass, W. & Al-Hakimi, A. N. (2008). Spectrochim. Acta A Mol. Biomol. Spectrosc. 71, 90–99. [DOI] [PubMed]
Fayos, J., Martínez-Ripoll, M., García-Mina, M. C., Gonzalez-Martínez, J. & Arrese, F. (1980). Acta Cryst. B36, 1952–1953.
Groom, C. R. & Allen, F. H. (2014). Angew. Chem. Int. Ed. 53, 662–671. [DOI] [PubMed]
Guo, Y.-N., Xu, G.-F., Gamez, P., Zhao, L., Lin, S.-Y., Deng, R., Tang, J.-K. & Zhang, H.-J. (2010). J. Am. Chem. Soc. 132, 8538–8539. [DOI] [PubMed]
Kitaev, Y. P., Buzykin, B. I. & Troepol’skaya, T. V. (1970). Russ. Chem. Rev. 39, 441–456.
Qin, D.-D., Yang, Z.-Y. & Qi, G.-F. (2009). Spectrochim. Acta A Mol. Biomol. Spectrosc. 74, 415–420. [DOI] [PubMed]
Ramamohan, L., Shikkargol, R. K., Angadi, S. D. & Kulkarni, V. H. (1995). Asian J. Pure Appl. Chem. 1, 86–89.
Rollas, S. & Küçükgüzel, Ş. G. (2007). Molecules, 12, 1910–1939. [DOI] [PMC free article] [PubMed]
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [DOI] [PubMed]
Tai, X.-S., Xu, J., Feng, Y.-M. & Liang, Z.-P. (2008). Acta Cryst. E64, o905. [DOI] [PMC free article] [PubMed]
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Associated Data

This section collects any data citations, data availability statements, or supplementary materials included in this article.

Supplementary Materials

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S2056989016003686/xu5885sup1.cif

e-72-00467-sup1.cif^{(16.2KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989016003686/xu5885Isup2.hkl

e-72-00467-Isup2.hkl^{(99KB, hkl)}

Click here for additional data file.^{(7.4KB, cml)}

Supporting information file. DOI: 10.1107/S2056989016003686/xu5885Isup3.cml

CCDC reference: 1457201

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

[bb1] Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.

[bb2] Chang, J.-G., He, G.-F. & Li, Y.-F. (2007). Acta Cryst. E63, o3982.

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PERMALINK

Crystal structure of (E,E)-2′,4′-dihydroxyacetophenone azine dimethylformamide disolvate

Wen-Juan Li

Hong-Fei Han

Abstract

Chemical context

Structural commentary