organic compounds
N-Ethyl-2-[1-(2-hydroxynaphthalen-1-yl)ethylidene]hydrazinecarbothioamide
aDepartment of Chemistry, Keene State College, 229 Main Street, Keene, NH 03435-2001, USA
*Correspondence e-mail: jjasinski@keene.edu
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
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Data collection: CrysAlis PRO (Agilent, 2012); cell 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
10.1107/S1600536814012057/bt6981sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536814012057/bt6981Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536814012057/bt6981Isup3.cml
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.
All of the H atoms were placed in their calculated positions and then refined using the riding model with Atom—H lengths of 0.95Å (CH), 0.99Å (CH2), 0.98Å (CH3), 0.88Å (NH) or 0.84Å (OH). Isotropic displacement parameters for these atoms were set to 1.2 (CH, CH2, NH) or 1.5 (CH3, OH) times Ueq of the parent atom. Idealised Me refined as rotating group. Idealised tetrahedral OH refined as rotating group.
Data collection: CrysAlis PRO (Agilent, 2012); cell
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).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. |
C15H17N3OS | Z = 2 |
Mr = 287.38 | F(000) = 304 |
Triclinic, P1 | Dx = 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 |
Agilent Eos Gemini diffractometer | 2710 independent reflections |
Radiation source: Enhance (Cu) X-ray Source | 2365 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.032 |
Detector resolution: 16.0416 pixels mm-1 | θmax = 71.4°, θmin = 4.8° |
ω scans | h = −10→10 |
Absorption correction: multi-scan (CrysAlis PRO and CrysAlis RED; Agilent, 2012) | k = −10→11 |
Tmin = 0.429, Tmax = 1.000 | l = −11→9 |
4327 measured reflections |
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(Fo2) + (0.0898P)2 + 0.2589P] where P = (Fo2 + 2Fc2)/3 |
S = 1.06 | (Δ/σ)max < 0.001 |
2710 reflections | Δρmax = 0.41 e Å−3 |
184 parameters | Δρmin = −0.41 e Å−3 |
0 restraints |
C15H17N3OS | γ = 93.990 (7)° |
Mr = 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)° |
Agilent Eos Gemini diffractometer | 2710 independent reflections |
Absorption correction: multi-scan (CrysAlis PRO and CrysAlis RED; Agilent, 2012) | 2365 reflections with I > 2σ(I) |
Tmin = 0.429, Tmax = 1.000 | Rint = 0.032 |
4327 measured reflections |
R[F2 > 2σ(F2)] = 0.054 | 0 restraints |
wR(F2) = 0.153 | H-atom parameters constrained |
S = 1.06 | Δρmax = 0.41 e Å−3 |
2710 reflections | Δρmin = −0.41 e Å−3 |
184 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
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* |
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) |
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) |
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. |
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.
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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.