N-Ethyl-2-[1-(2-hy­droxy­naphthalen-1-yl)ethyl­idene]hydrazinecarbo­thio­amide

Anderson, B.J.; Shalit, Z.A.; Jasinski, J.P.

doi:10.1107/S1600536814012057

organic compounds

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ISSN: 2056-9890

Volume 70| Part 6| June 2014| Page o732

doi:10.1107/S1600536814012057

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N-Ethyl-2-[1-(2-hydroxynaphthalen-1-yl)ethylidene]hydrazinecarbothioamide

Brian J. Anderson,^a Zachary A. Shalit ^a and Jerry P. Jasinski ^a ^*

^aDepartment of Chemistry, Keene State College, 229 Main Street, Keene, NH 03435-2001, USA
^*Correspondence e-mail: jjasinski@keene.edu

(Received 23 May 2014; accepted 23 May 2014; online 31 May 2014)

In the title compound, C₁₅H₁₇N₃OS, the dihedral angle between the mean planes of the 2-hydroxynapthyl ring system and the hydrazinecarbothioamide group is 73.7 (3)°. In the crystal, weak O—H⋯S and C—H⋯O interactions and π–π stacking interactions involving one of the hydroxynapthyl rings with a centroid–centroid distance of 3.6648 (14) Å are observed, forming infinite chains along [010]. In addition, N—H⋯S interactions occur.

CCDC reference: 1005053

Related literature

For the biological activity of thiosemicarbazones, see: Chellan et al. (2010 ). For binding motifs of thiosemicarbazones, see: Lobana et al. (2009 ). For thiosemicarbazones as ligands in catalysis, see: Xie et al. (2010 ). For related structures, see: Anderson et al. (2012 , 2013a ,b ). For standard bond lengths, see: Allen et al. (1987 ).

Experimental

Crystal data

C₁₅H₁₇N₃OS
M_r = 287.38
Triclinic, $[P \overline 1]$
a = 8.8988 (7) Å
b = 9.2993 (8) Å
c = 9.4821 (5) Å
α = 92.525 (6)°
β = 113.034 (7)°
γ = 93.990 (7)°
V = 718.18 (10) Å³
Z = 2
Cu Kα radiation
μ = 1.99 mm⁻¹
T = 173 K
0.42 × 0.22 × 0.14 mm

Data collection

Agilent Eos Gemini diffractometer
Absorption correction: multi-scan (CrysAlis PRO and CrysAlis RED; Agilent, 2012 ) T_min = 0.429, T_max = 1.000
4327 measured reflections
2710 independent reflections
2365 reflections with I > 2σ(I)
R_int = 0.032

Refinement

R[F² > 2σ(F²)] = 0.054
wR(F²) = 0.153
S = 1.06
2710 reflections
184 parameters
H-atom parameters constrained
Δρ_max = 0.41 e Å⁻³
Δρ_min = −0.41 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯S1ⁱ	0.84	2.40	3.2349 (17)	171
C14—H14A⋯O1ⁱⁱ	0.99	2.49	3.474 (4)	171
N2—H2⋯S1ⁱⁱⁱ	0.88	2.79	3.548 (2)	145
Symmetry codes: (i) x, y-1, z; (ii) x, y+1, z; (iii) -x+1, -y+1, -z.

Data collection: CrysAlis PRO (Agilent, 2012); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Agilent, 2012); program(s) used to solve structure: SUPERFLIP (Palatinus & Chapuis, 2007 ; Palatinus & van der Lee, 2008 ; Palatinus et al., 2012 ).; program(s) used to refine structure: SHELXL2012 (Sheldrick, 2008 ); molecular graphics: OLEX2 (Dolomanov et al., 2009 ); software used to prepare material for publication: OLEX2.

Supporting information

CCDC reference: 1005053

Crystal structure: contains datablock I. DOI: 10.1107/S1600536814012057/bt6981sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814012057/bt6981Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536814012057/bt6981Isup3.cml

checkCIF report

Comment top

Thiosemicarbazones are a versatile class of ligands that have been studied for their biological activity (Chellan et al., 2010), interesting binding motifs (Lobana et al., 2009), and their use as ligands in catalysis (Xie et al., 2010). We have previously reported the structure of three similar novel thiosemicarbazones (Anderson et al., 2012; Anderson et al., 2013a; Anderson et al., 2013b). Here, we report the synthesis and crystal structure of a new novel thiosemicarbazone ligand starting with 2'-hydroxy-1'-acetonaphthone and 4-ethyl-thio-semicarbazide, C₁₅H₁₇N₃OS.

In the title compound, the dihedral angle between the mean planes of the 2-hydroxynapthyl ring and the hydrazinecarbothioamide group (N3/N2/C1/S1/N1) is 73.7 (3)°. Bond lengths are in normal ranges (Allen et al., 1987). In the crystal, weak O1—H1···S1 and C14—H14A···O1 intermolecular interactions and π–π stacking interactions involving one of the hydroxynapthyl rings are observed forming infinite polymeric chains along [010] (Cg2—Cg2 = 3.6648 (14)Å; 2-x, 1-y, -z; Cg2 = C7—C12). In addition, there are N-H···S interactions stabilizing the crystal structure.

Related literature top

For the biological activity of thiosemicarbazones, see: Chellan et al. (2010). For binding motifs of thiosemicarbazones, see: Lobana et al. (2009). For thiosemicarbazones as ligands in catalysis, see: Xie et al. (2010). For related structures, see: Anderson et al. (2012, 2013a,b). For standard bond lengths, see: Allen et al. (1987).

Experimental top

A 25 mL round bottom flask was charged with 0.2052 g (1.102 mmol) 2'-hydroxy-1'-acetonaphthone, and 0.1341 g (1.125 mmol) 4-ethyl-thio-semicarbazide and in 5 mL of 1:1 ratio H₂O to ETOH. The resulting slurry was refluxed for 96 hours (Fig. 3). After reflux the opaque solution was transferred to a separatory funnel to which dichloromethane and water were added. The organic layer was separated and the aqueous layer was extracted twice with 5 mL DCM. The organic layers were combined, washed with brine and dried with magnesium sulfate, and the solvent was removed in vacuo to yield a colorless oil. The oil was the dissolved in minimal 343° K acetonitrile and left to slowly cool to 273° K, after 24 days colorless crystals were observed. m.p. 444–446 K.

Computing details top

Data collection: CrysAlis PRO (Agilent, 2012); cell refinement: CrysAlis PRO (Agilent, 2012); data reduction: CrysAlis RED (Agilent, 2012); program(s) used to solve structure: SUPERFLIP (Palatinus & Chapuis, 2007; Palatinus & van der Lee, 2008; Palatinus et al., 2012).; program(s) used to refine structure: SHELXL2012 (Sheldrick, 2008); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

Figures top

	Fig. 1. ORTEP drawing of C₁₅H₁₇N₃OS, showing the labeling scheme with 30% probability displacement ellipsoids.
	Fig. 2. Molecular packing for the title compound viewed along the a axis. Dashed lines indicate weak O1—H1···S1 and C14—H14A···O1 intermolecular interactions forming infinite polymeric chains along [010].
	Fig. 3. Reaction scheme.

N-Ethyl-2-[1-(2-hydroxynaphthalen-1-yl)ethylidene]hydrazinecarbothioamide top

Crystal data top

C₁₅H₁₇N₃OS	Z = 2
M_r = 287.38	F(000) = 304
Triclinic, P1	D_x = 1.329 Mg m⁻³
a = 8.8988 (7) Å	Cu Kα radiation, λ = 1.54184 Å
b = 9.2993 (8) Å	Cell parameters from 1994 reflections
c = 9.4821 (5) Å	θ = 4.8–71.3°
α = 92.525 (6)°	µ = 1.99 mm⁻¹
β = 113.034 (7)°	T = 173 K
γ = 93.990 (7)°	Irregular, colourless
V = 718.18 (10) Å³	0.42 × 0.22 × 0.14 mm

Data collection top

Agilent Eos Gemini diffractometer	2710 independent reflections
Radiation source: Enhance (Cu) X-ray Source	2365 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.032
Detector resolution: 16.0416 pixels mm^-1	θ_max = 71.4°, θ_min = 4.8°
ω scans	h = −10→10
Absorption correction: multi-scan (CrysAlis PRO and CrysAlis RED; Agilent, 2012)	k = −10→11
T_min = 0.429, T_max = 1.000	l = −11→9
4327 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.054	H-atom parameters constrained
wR(F²) = 0.153	w = 1/[σ²(F_o²) + (0.0898P)² + 0.2589P] where P = (F_o² + 2F_c²)/3
S = 1.06	(Δ/σ)_max < 0.001
2710 reflections	Δρ_max = 0.41 e Å⁻³
184 parameters	Δρ_min = −0.41 e Å⁻³
0 restraints

Crystal data top

C₁₅H₁₇N₃OS	γ = 93.990 (7)°
M_r = 287.38	V = 718.18 (10) Å³
Triclinic, P1	Z = 2
a = 8.8988 (7) Å	Cu Kα radiation
b = 9.2993 (8) Å	µ = 1.99 mm⁻¹
c = 9.4821 (5) Å	T = 173 K
α = 92.525 (6)°	0.42 × 0.22 × 0.14 mm
β = 113.034 (7)°

Data collection top

Agilent Eos Gemini diffractometer	2710 independent reflections
Absorption correction: multi-scan (CrysAlis PRO and CrysAlis RED; Agilent, 2012)	2365 reflections with I > 2σ(I)
T_min = 0.429, T_max = 1.000	R_int = 0.032
4327 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.054	0 restraints
wR(F²) = 0.153	H-atom parameters constrained
S = 1.06	Δρ_max = 0.41 e Å⁻³
2710 reflections	Δρ_min = −0.41 e Å⁻³
184 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.

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

	x	y	z	U_iso*/U_eq
S1	0.53047 (7)	0.69555 (5)	0.11487 (6)	0.0286 (2)
O1	0.6330 (2)	0.03677 (17)	0.2160 (2)	0.0360 (4)
H1	0.6056	−0.0495	0.1793	0.054*
N1	0.6310 (3)	0.6503 (2)	0.4127 (2)	0.0342 (5)
H1A	0.6824	0.5980	0.4893	0.041*
N2	0.6777 (2)	0.47722 (19)	0.2599 (2)	0.0242 (4)
H2	0.6733	0.4430	0.1702	0.029*
N3	0.7469 (2)	0.40209 (19)	0.3892 (2)	0.0234 (4)
C1	0.6168 (3)	0.6042 (2)	0.2735 (2)	0.0226 (5)
C2	0.8136 (3)	0.2868 (2)	0.3759 (3)	0.0230 (5)
C3	0.8262 (3)	0.2283 (2)	0.2325 (2)	0.0219 (4)
C4	0.7379 (3)	0.1000 (2)	0.1585 (3)	0.0251 (5)
C5	0.7515 (3)	0.0388 (2)	0.0254 (3)	0.0284 (5)
H5	0.6860	−0.0475	−0.0267	0.034*
C6	0.8583 (3)	0.1036 (2)	−0.0279 (3)	0.0278 (5)
H6	0.8656	0.0625	−0.1182	0.033*
C7	0.9594 (3)	0.2317 (2)	0.0491 (3)	0.0249 (5)
C8	1.0824 (3)	0.2928 (3)	0.0032 (3)	0.0294 (5)
H8	1.0948	0.2499	−0.0839	0.035*
C9	1.1834 (3)	0.4128 (3)	0.0832 (3)	0.0319 (5)
H9	1.2667	0.4516	0.0527	0.038*
C10	1.1634 (3)	0.4782 (2)	0.2102 (3)	0.0298 (5)
H10	1.2323	0.5623	0.2641	0.036*
C11	1.0455 (3)	0.4222 (2)	0.2576 (3)	0.0245 (5)
H11	1.0332	0.4684	0.3433	0.029*
C12	0.9418 (2)	0.2955 (2)	0.1797 (2)	0.0216 (4)
C13	0.8917 (3)	0.2093 (3)	0.5182 (3)	0.0344 (6)
H13A	1.0106	0.2152	0.5473	0.052*
H13B	0.8472	0.1076	0.4985	0.052*
H13C	0.8686	0.2543	0.6021	0.052*
C14	0.5673 (4)	0.7823 (4)	0.4484 (3)	0.0555 (9)
H14A	0.5943	0.8613	0.3931	0.067*
H14B	0.4462	0.7659	0.4092	0.067*
C15	0.6293 (6)	0.8273 (5)	0.6067 (4)	0.0845 (15)
H15A	0.5734	0.9099	0.6224	0.127*
H15B	0.7473	0.8558	0.6438	0.127*
H15C	0.6102	0.7475	0.6636	0.127*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0383 (4)	0.0169 (3)	0.0243 (3)	0.0057 (2)	0.0052 (2)	0.0014 (2)
O1	0.0362 (9)	0.0208 (8)	0.0520 (11)	−0.0063 (7)	0.0208 (8)	−0.0064 (7)
N1	0.0440 (12)	0.0314 (11)	0.0233 (10)	0.0204 (9)	0.0066 (9)	0.0003 (8)
N2	0.0329 (10)	0.0193 (9)	0.0190 (9)	0.0090 (7)	0.0078 (8)	0.0005 (7)
N3	0.0277 (9)	0.0196 (9)	0.0206 (9)	0.0026 (7)	0.0071 (7)	0.0008 (7)
C1	0.0210 (10)	0.0188 (10)	0.0236 (11)	0.0022 (8)	0.0044 (8)	−0.0017 (8)
C2	0.0221 (10)	0.0173 (10)	0.0273 (11)	0.0010 (8)	0.0075 (9)	0.0023 (8)
C3	0.0218 (10)	0.0158 (9)	0.0249 (11)	0.0050 (8)	0.0051 (8)	0.0021 (8)
C4	0.0215 (10)	0.0164 (10)	0.0331 (12)	0.0054 (8)	0.0054 (9)	0.0015 (8)
C5	0.0245 (11)	0.0184 (10)	0.0339 (12)	0.0052 (8)	0.0026 (9)	−0.0042 (9)
C6	0.0281 (11)	0.0261 (11)	0.0238 (11)	0.0115 (9)	0.0037 (9)	−0.0042 (9)
C7	0.0248 (11)	0.0235 (10)	0.0240 (11)	0.0100 (9)	0.0057 (9)	0.0048 (8)
C8	0.0339 (12)	0.0310 (12)	0.0253 (11)	0.0120 (10)	0.0119 (10)	0.0072 (9)
C9	0.0314 (12)	0.0323 (12)	0.0357 (13)	0.0065 (10)	0.0156 (10)	0.0124 (10)
C10	0.0274 (11)	0.0242 (11)	0.0339 (12)	0.0005 (9)	0.0078 (10)	0.0052 (9)
C11	0.0264 (11)	0.0194 (10)	0.0247 (11)	0.0040 (8)	0.0067 (9)	0.0019 (8)
C12	0.0205 (10)	0.0176 (10)	0.0222 (10)	0.0062 (8)	0.0029 (8)	0.0039 (8)
C13	0.0469 (14)	0.0273 (12)	0.0293 (13)	0.0120 (11)	0.0135 (11)	0.0078 (10)
C14	0.072 (2)	0.0528 (17)	0.0360 (15)	0.0411 (16)	0.0101 (14)	−0.0068 (13)
C15	0.107 (3)	0.074 (2)	0.051 (2)	0.062 (2)	0.002 (2)	−0.0201 (18)

Geometric parameters (Å, º) top

S1—C1	1.695 (2)	C7—C8	1.420 (3)
O1—H1	0.8400	C7—C12	1.418 (3)
O1—C4	1.366 (3)	C8—H8	0.9500
N1—H1A	0.8800	C8—C9	1.372 (4)
N1—C1	1.324 (3)	C9—H9	0.9500
N1—C14	1.468 (3)	C9—C10	1.404 (4)
N2—H2	0.8800	C10—H10	0.9500
N2—N3	1.384 (3)	C10—C11	1.374 (3)
N2—C1	1.355 (3)	C11—H11	0.9500
N3—C2	1.286 (3)	C11—C12	1.423 (3)
C2—C3	1.491 (3)	C13—H13A	0.9800
C2—C13	1.499 (3)	C13—H13B	0.9800
C3—C4	1.378 (3)	C13—H13C	0.9800
C3—C12	1.428 (3)	C14—H14A	0.9900
C4—C5	1.413 (3)	C14—H14B	0.9900
C5—H5	0.9500	C14—C15	1.413 (4)
C5—C6	1.358 (3)	C15—H15A	0.9800
C6—H6	0.9500	C15—H15B	0.9800
C6—C7	1.422 (3)	C15—H15C	0.9800

C4—O1—H1	109.5	C9—C8—H8	119.6
C1—N1—H1A	117.7	C8—C9—H9	120.1
C1—N1—C14	124.6 (2)	C8—C9—C10	119.8 (2)
C14—N1—H1A	117.7	C10—C9—H9	120.1
N3—N2—H2	120.5	C9—C10—H10	119.5
C1—N2—H2	120.5	C11—C10—C9	120.9 (2)
C1—N2—N3	118.96 (18)	C11—C10—H10	119.5
C2—N3—N2	117.91 (18)	C10—C11—H11	119.7
N1—C1—S1	123.94 (17)	C10—C11—C12	120.6 (2)
N1—C1—N2	117.0 (2)	C12—C11—H11	119.7
N2—C1—S1	119.01 (16)	C7—C12—C3	119.48 (19)
N3—C2—C3	125.3 (2)	C7—C12—C11	118.3 (2)
N3—C2—C13	117.1 (2)	C11—C12—C3	122.1 (2)
C3—C2—C13	117.53 (19)	C2—C13—H13A	109.5
C4—C3—C2	119.75 (19)	C2—C13—H13B	109.5
C4—C3—C12	119.3 (2)	C2—C13—H13C	109.5
C12—C3—C2	120.65 (18)	H13A—C13—H13B	109.5
O1—C4—C3	117.4 (2)	H13A—C13—H13C	109.5
O1—C4—C5	121.37 (19)	H13B—C13—H13C	109.5
C3—C4—C5	121.2 (2)	N1—C14—H14A	108.7
C4—C5—H5	120.1	N1—C14—H14B	108.7
C6—C5—C4	119.9 (2)	H14A—C14—H14B	107.6
C6—C5—H5	120.1	C15—C14—N1	114.2 (3)
C5—C6—H6	119.4	C15—C14—H14A	108.7
C5—C6—C7	121.3 (2)	C15—C14—H14B	108.7
C7—C6—H6	119.4	C14—C15—H15A	109.5
C8—C7—C6	121.8 (2)	C14—C15—H15B	109.5
C12—C7—C6	118.7 (2)	C14—C15—H15C	109.5
C12—C7—C8	119.4 (2)	H15A—C15—H15B	109.5
C7—C8—H8	119.6	H15A—C15—H15C	109.5
C9—C8—C7	120.8 (2)	H15B—C15—H15C	109.5

O1—C4—C5—C6	−179.3 (2)	C5—C6—C7—C12	−2.9 (3)
N2—N3—C2—C3	1.4 (3)	C6—C7—C8—C9	−177.1 (2)
N2—N3—C2—C13	178.41 (19)	C6—C7—C12—C3	1.3 (3)
N3—N2—C1—S1	−179.44 (15)	C6—C7—C12—C11	178.85 (18)
N3—N2—C1—N1	1.5 (3)	C7—C8—C9—C10	−1.3 (3)
N3—C2—C3—C4	−111.9 (2)	C8—C7—C12—C3	−175.52 (19)
N3—C2—C3—C12	74.7 (3)	C8—C7—C12—C11	2.0 (3)
C1—N1—C14—C15	−165.9 (3)	C8—C9—C10—C11	1.2 (4)
C1—N2—N3—C2	−175.50 (18)	C9—C10—C11—C12	0.6 (3)
C2—C3—C4—O1	4.3 (3)	C10—C11—C12—C3	175.3 (2)
C2—C3—C4—C5	−177.72 (19)	C10—C11—C12—C7	−2.1 (3)
C2—C3—C12—C7	175.56 (18)	C12—C3—C4—O1	177.75 (18)
C2—C3—C12—C11	−1.9 (3)	C12—C3—C4—C5	−4.2 (3)
C3—C4—C5—C6	2.8 (3)	C12—C7—C8—C9	−0.3 (3)
C4—C3—C12—C7	2.1 (3)	C13—C2—C3—C4	71.2 (3)
C4—C3—C12—C11	−175.27 (19)	C13—C2—C3—C12	−102.2 (2)
C4—C5—C6—C7	0.9 (3)	C14—N1—C1—S1	3.2 (4)
C5—C6—C7—C8	173.9 (2)	C14—N1—C1—N2	−177.7 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···S1ⁱ	0.84	2.40	3.2349 (17)	171
C14—H14A···O1ⁱⁱ	0.99	2.49	3.474 (4)	171
N2—H2···S1ⁱⁱⁱ	0.88	2.79	3.548 (2)	145

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···S1ⁱ	0.84	2.40	3.2349 (17)	170.8
C14—H14A···O1ⁱⁱ	0.99	2.49	3.474 (4)	170.9
N2—H2···S1ⁱⁱⁱ	0.88	2.79	3.548 (2)	144.8

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

Acknowledgements

JPJ acknowledges the NSF–MRI program (grant No. CHE-1039027) for funds to purchase the X-ray diffractometer.

References

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Volume 70| Part 6| June 2014| Page o732

doi:10.1107/S1600536814012057

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

N-Ethyl-2-[1-(2-hy­dr­oxy­naphthalen-1-yl)ethyl­­idene]hydrazinecarbo­thio­amide

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

N-Ethyl-2-[1-(2-hydroxynaphthalen-1-yl)ethylidene]hydrazinecarbothioamide