Crystal structure of 1-((1E)-{(E)-2-[(2-hydroxy­naphthalen-1-yl)methyl­idene]hydrazin-1-yl­idene}meth­yl)naphthalen-2-ol

Vijayan, P.; Viswanathamurthi, P.; Fleck, M.; Paramasivam, S.; Nanjappagounder, P.M.

doi:10.1107/S205698901500972X

organic compounds

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Crystal structure of 1-((1E)-{(E)-2-[(2-hydroxynaphthalen-1-yl)methylidene]hydrazin-1-ylidene}methyl)naphthalen-2-ol

Paranthaman Vijayan,^a Periasamy Viswanathamurthi,^a ^* Michel Fleck,^b Sugumar Paramasivam ^c and Ponnuswamy Mondikalipudur Nanjappagounder ^c

^aDepartment of Chemistry, Periyar University, Salem 636 011, India, ^bInstitute of Mineralogy and Crystallography Geozentrum, University of Vienna, Althanstrasse 14, A-1090 Vienna, Austria, and ^cCentre of Advanced Studies in Crystallography and Biophysics, University of Madras, Guindy Campus, Chennai 600 025, India
^*Correspondence e-mail: viswanathamurthi72@gmail.com

Edited by W. T. A. Harrison, University of Aberdeen, Scotland (Received 14 April 2015; accepted 20 May 2015; online 28 May 2015)

The complete molecule of the title compound, C₂₂H₁₆N₂O₂, is generated by a crystallographic inversion centre at the mid-point of the central N—N bond. Two intramolecular O—H⋯N hydrogen bonds occur.

Keywords: crystal structure; Schiff base derivative; intramolecular hydrogen bonding.

CCDC reference: 1401958

1. Related literature

For general background to Schiff base derivatives, see: Hoshino (1998 ); Kalaivani et al. (2013 ); Vijayan et al. (2014 ).

2. Experimental

2.1. Crystal data

C₂₂H₁₆N₂O₂
M_r = 340.37
Monoclinic, P 2₁ /n
a = 8.5680 (7) Å
b = 6.1020 (5) Å
c = 15.9870 (6) Å
β = 91.191 (5)°
V = 835.65 (10) Å³
Z = 2
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 293 K
0.22 × 0.20 × 0.18 mm

2.2. Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2008 ) T_min = 0.981, T_max = 0.984
1907 measured reflections
1907 independent reflections
1859 reflections with I > 2σ(I)

2.3. Refinement

R[F² > 2σ(F²)] = 0.007
wR(F²) = 0.019
S = 1.03
1907 reflections
122 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.02 e Å⁻³
Δρ_min = −0.08 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.98	1.67 (1)	2.5671 (3)	151 (1)

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ).

Supporting information

CCDC reference: 1401958

Crystal structure: contains datablocks global, I. DOI: 10.1107/S205698901500972X/hb7408sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S205698901500972X/hb7408Isup2.hkl

Supporting information file. DOI: 10.1107/S205698901500972X/hb7408Isup3.cml

checkCIF report

Comment top

Schiff bases are important ligands, as moderate electron donors with a chelating structure and control the behaviour of metal ions in a diverse range of applications (Hoshino, 1998). Dithiocarbazate compounds are an important class of Schiff bases which can be easily obtained by condensation of dithiocarbazides with aldehydes or ketones. In particular hydrazone containing naphthalene ring compounds have drawn much attention because of their biological activities such as DNA/BSA binding affinities and anticancer activities in vitro (Kalaivani et al., 2013; Vijayan et al., 2014).

The ORTEP plot of the molecule is shown in Fig.1. The title compound (I), crystallized in the monoclinic spacegroup P2₁/n with half molecule in the asymmetric unit. Pair of molecules related by an crystallographic inversion centre generate another half of the molecule.

Related literature top

For general background to Schiff base derivatives, see: Hoshino (1998); Kalaivani et al. (2013); Vijayan et al. (2014).

Experimental top

The title compound was obtained by the reaction of S-benzyldithiocarbazate and 2-Hydroxy-1-napthaldehyde in boiling ethanol. The unexpected formation of the hydrazone was probably due to the decomposition of S-benzyldithiocarbazate in solution resulting in the formation of hydrazine, which then reacted with 2-hydroxy-1-napthaldehyde to form the corresponding hydrazone. The dithiocarbazates are known to decompose on heating.

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); 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, showing displacement ellipsoids drawn at 50% probability level.

1-((1E)-{(E)-2-[(2-Hydroxynaphthalen-1-yl)methylidene]hydrazin-1-ylidene}methyl)naphthalen-2-ol top

Crystal data top

C₂₂H₁₆N₂O₂	F(000) = 356
M_r = 340.37	D_x = 1.353 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1859 reflections
a = 8.5680 (7) Å	θ = 2.6–27.5°
b = 6.1020 (5) Å	µ = 0.09 mm⁻¹
c = 15.9870 (6) Å	T = 293 K
β = 91.191 (5)°	Block, yellow
V = 835.65 (10) Å³	0.22 × 0.20 × 0.18 mm
Z = 2

Data collection top

Bruker SMART APEXII CCD diffractometer	1907 independent reflections
Radiation source: fine-focus sealed tube	1859 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.0000
ω and ϕ scans	θ_max = 27.5°, θ_min = 2.6°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −11→11
T_min = 0.981, T_max = 0.984	k = 0→7
1907 measured reflections	l = 0→20

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)] = 0.007	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.019	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ²(F_o²) + (0.008P)² where P = (F_o² + 2F_c²)/3
1907 reflections	(Δ/σ)_max = 0.001
122 parameters	Δρ_max = 0.02 e Å⁻³
1 restraint	Δρ_min = −0.08 e Å⁻³

Crystal data top

C₂₂H₁₆N₂O₂	V = 835.65 (10) Å³
M_r = 340.37	Z = 2
Monoclinic, P2₁/n	Mo Kα radiation
a = 8.5680 (7) Å	µ = 0.09 mm⁻¹
b = 6.1020 (5) Å	T = 293 K
c = 15.9870 (6) Å	0.22 × 0.20 × 0.18 mm
β = 91.191 (5)°

Data collection top

Bruker SMART APEXII CCD diffractometer	1907 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2008)	1859 reflections with I > 2σ(I)
T_min = 0.981, T_max = 0.984	R_int = 0.0000
1907 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.007	1 restraint
wR(F²) = 0.019	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.02 e Å⁻³
1907 reflections	Δρ_min = −0.08 e Å⁻³
122 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	0.37033 (2)	0.02490 (3)	0.395255 (11)	0.03120 (4)
C2	0.32482 (2)	−0.16485 (3)	0.350605 (13)	0.03653 (5)
H2	0.2610	−0.2683	0.3755	0.044*
C3	0.37391 (2)	−0.19647 (3)	0.271551 (13)	0.03672 (5)
H3	0.3450	−0.3240	0.2434	0.044*
C4	0.46786 (2)	−0.04107 (3)	0.230675 (12)	0.03129 (5)
C5	0.51123 (3)	−0.06977 (4)	0.146509 (13)	0.04195 (5)
H5	0.4815	−0.1967	0.1182	0.050*
C6	0.59566 (3)	0.08510 (5)	0.106276 (13)	0.04842 (6)
H6	0.6213	0.0654	0.0505	0.058*
C7	0.64395 (3)	0.27462 (5)	0.149184 (13)	0.04576 (6)
H7	0.7021	0.3802	0.1217	0.055*
C8	0.60616 (2)	0.30547 (4)	0.231137 (12)	0.03661 (5)
H8	0.6408	0.4310	0.2588	0.044*
C9	0.51573 (2)	0.15099 (3)	0.274652 (11)	0.02726 (4)
C10	0.46705 (2)	0.18089 (3)	0.359484 (10)	0.02658 (4)
C11	0.51614 (2)	0.37178 (3)	0.406697 (11)	0.02991 (4)
H11	0.5827	0.4727	0.3824	0.036*
N1	0.46961 (2)	0.40510 (3)	0.481933 (10)	0.03414 (4)
O1	0.31470 (2)	0.04548 (3)	0.472921 (9)	0.04471 (5)
H1	0.3596 (5)	0.1824 (7)	0.4943 (2)	0.0995 (13)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.03470 (9)	0.03336 (10)	0.02553 (9)	0.00099 (8)	0.00052 (7)	−0.00058 (7)
C2	0.03940 (11)	0.03200 (10)	0.03805 (11)	−0.00574 (8)	−0.00259 (8)	0.00167 (8)
C3	0.03929 (11)	0.03106 (10)	0.03943 (11)	0.00132 (8)	−0.00822 (8)	−0.00859 (8)
C4	0.02942 (9)	0.03540 (10)	0.02889 (9)	0.00595 (8)	−0.00317 (7)	−0.00776 (8)
C5	0.04097 (11)	0.05126 (13)	0.03346 (11)	0.00604 (10)	−0.00287 (8)	−0.01694 (9)
C6	0.04610 (12)	0.07303 (17)	0.02636 (10)	0.00235 (12)	0.00672 (9)	−0.01219 (10)
C7	0.04615 (12)	0.06073 (15)	0.03086 (10)	−0.00308 (11)	0.01184 (9)	−0.00236 (10)
C8	0.03867 (10)	0.04315 (12)	0.02823 (10)	−0.00353 (9)	0.00582 (8)	−0.00574 (8)
C9	0.02591 (8)	0.03176 (9)	0.02405 (8)	0.00337 (7)	−0.00108 (6)	−0.00519 (7)
C10	0.02861 (9)	0.02830 (9)	0.02281 (8)	0.00107 (7)	−0.00030 (6)	−0.00319 (7)
C11	0.03341 (9)	0.03091 (10)	0.02545 (9)	−0.00130 (7)	0.00150 (7)	−0.00289 (7)
N1	0.04353 (9)	0.03257 (9)	0.02637 (8)	−0.00328 (7)	0.00204 (7)	−0.00689 (7)
O1	0.05713 (10)	0.04698 (10)	0.03052 (8)	−0.01041 (8)	0.01283 (7)	−0.00151 (7)

Geometric parameters (Å, º) top

C1—O1	1.3451 (2)	C6—H6	0.9300
C1—C10	1.3927 (3)	C7—C8	1.3691 (3)
C1—C2	1.4109 (3)	C7—H7	0.9300
C2—C3	1.3541 (3)	C8—C9	1.4125 (3)
C2—H2	0.9300	C8—H8	0.9300
C3—C4	1.4129 (3)	C9—C10	1.4388 (2)
C3—H3	0.9300	C10—C11	1.4458 (3)
C4—C5	1.4142 (3)	C11—N1	1.2911 (2)
C4—C9	1.4226 (3)	C11—H11	0.9300
C5—C6	1.3600 (4)	N1—N1ⁱ	1.3906 (3)
C5—H5	0.9300	O1—H1	0.978 (4)
C6—C7	1.4026 (4)

O1—C1—C10	122.721 (18)	C8—C7—C6	120.54 (2)
O1—C1—C2	116.367 (18)	C8—C7—H7	119.7
C10—C1—C2	120.911 (18)	C6—C7—H7	119.7
C3—C2—C1	120.079 (19)	C7—C8—C9	121.51 (2)
C3—C2—H2	120.0	C7—C8—H8	119.2
C1—C2—H2	120.0	C9—C8—H8	119.2
C2—C3—C4	121.809 (19)	C8—C9—C4	117.502 (17)
C2—C3—H3	119.1	C8—C9—C10	123.528 (18)
C4—C3—H3	119.1	C4—C9—C10	118.951 (18)
C3—C4—C5	121.360 (19)	C1—C10—C9	119.145 (17)
C3—C4—C9	119.045 (17)	C1—C10—C11	120.359 (17)
C5—C4—C9	119.570 (19)	C9—C10—C11	120.491 (17)
C6—C5—C4	121.12 (2)	N1—C11—C10	121.408 (18)
C6—C5—H5	119.4	N1—C11—H11	119.3
C4—C5—H5	119.4	C10—C11—H11	119.3
C5—C6—C7	119.739 (19)	C11—N1—N1ⁱ	113.45 (2)
C5—C6—H6	120.1	C1—O1—H1	104.9 (2)
C7—C6—H6	120.1

O1—C1—C2—C3	179.043 (18)	C3—C4—C9—C10	0.06 (3)
C10—C1—C2—C3	−0.64 (3)	C5—C4—C9—C10	178.266 (17)
C1—C2—C3—C4	−1.51 (3)	O1—C1—C10—C9	−177.234 (17)
C2—C3—C4—C5	−176.393 (19)	C2—C1—C10—C9	2.43 (3)
C2—C3—C4—C9	1.78 (3)	O1—C1—C10—C11	1.96 (3)
C3—C4—C5—C6	176.95 (2)	C2—C1—C10—C11	−178.377 (17)
C9—C4—C5—C6	−1.21 (3)	C8—C9—C10—C1	176.247 (18)
C4—C5—C6—C7	1.46 (4)	C4—C9—C10—C1	−2.11 (3)
C5—C6—C7—C8	−0.31 (4)	C8—C9—C10—C11	−2.94 (3)
C6—C7—C8—C9	−1.12 (4)	C4—C9—C10—C11	178.703 (16)
C7—C8—C9—C4	1.33 (3)	C1—C10—C11—N1	−1.45 (3)
C7—C8—C9—C10	−177.044 (19)	C9—C10—C11—N1	177.730 (17)
C3—C4—C9—C8	−178.391 (18)	C10—C11—N1—N1ⁱ	179.073 (19)
C5—C4—C9—C8	−0.19 (3)

Symmetry code: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.98	1.67 (1)	2.5671 (3)	151 (1)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.98	1.668 (4)	2.5671 (3)	150.9 (3)

Acknowledgements

PV acknowledges the University Grants Commission (UGC), Government of India, New Delhi, for financial support in the form of a major research project No. F·No.40–66/2011 (SR).

References

Bruker (2008). APEX2, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Hoshino, N. (1998). Coord. Chem. Rev. 174. 77–108. Google Scholar
Kalaivani, P., Prabhakaran, R., Poornima, P., Huang, R., Hornebecq, V., Dallemer, F., Vijaya Padma, V. & Natarajan, K. (2013). RSC Adv. 3, 20363–20378. CSD CrossRef CAS Google Scholar
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Vijayan, P., Viswanathamurthi, P., Silambarasan, V., Velmurugan, D., Velmurugan, K., Nandhakumar, R., Butcher, R. J., Silambarasan, T. & Dhandapani, R. (2014). J. Organomet. Chem. 768, 163–177. CSD CrossRef CAS Google Scholar

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CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 71| Part 6| June 2015| Page o428

doi:10.1107/S205698901500972X

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

Crystal structure of 1-((1E)-{(E)-2-[(2-hy­droxy­naphthalen-1-yl)methyl­­idene]hydrazin-1-yl­­idene}meth­yl)naphthalen-2-ol

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 1-((1E)-{(E)-2-[(2-hydroxynaphthalen-1-yl)methylidene]hydrazin-1-ylidene}methyl)naphthalen-2-ol