organic compounds
N-phenylhydrazinecarbothioamide
of 2-[2-(hydroxyimino)-1-phenylpropylidene]-aDepartment of Chemistry, Keene State College, 229 Main Street, Keene, NH 03435-2001, USA
*Correspondence e-mail: jjasinski@keene.edu
In the title compound, C16H16N4OS, an intramolecular C—H⋯S hydrogen bond is observed. With the exception of the phenyl ring of the phenylpropylidene unit, the remainder of the molecule has an almost planar skeleton with an r.m.s. deviation of 0.121 (5) Å from the plane through the remaining 16 atoms. In the crystal O—H⋯N hydrogen bonds are observed between the terminal hydroxyimino groups, forming inverson dimers with R22(6) graph-set motifs. Additional C—H⋯N contacts stack the dimers along [100]. While no π—π interactions are present, weak C—H⋯O and O—H⋯Cg interactions are also observed and help stabilize the crystal packing.
Keywords: crystal structure; thiosemicarbazone; weak intermolecular interactions; O—H⋯π interactions.
CCDC reference: 1426205
1. Related literature
For thiosemicarbazone ligands and their metal complexes, see: Lobana et al. (2009, 2012). For the biological, anti-tumor and anti-fungal activity of palladium complexes with thiosemicarbazone ligands, see: Chellan et al. (2010). For the biological activity of a thiosemicarbazone ligand with terminal dimethyl substitution, see: Kowol et al. (2009). For related structures, see Anderson et al. (2012, 2013).
2. Experimental
2.1. Crystal data
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2.3. Refinement
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Data collection: CrysAlis PRO (Agilent, 2014); cell CrysAlis PRO; data reduction: CrysAlis RED (Agilent, 2014); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL (Sheldrick, 2015b); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2.
Supporting information
CCDC reference: 1426205
10.1107/S2056989015017739/sj5476sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S2056989015017739/sj5476Isup2.hkl
Supporting information file. DOI: 10.1107/S2056989015017739/sj5476Isup3.cml
In a 25 ml round bottom flask 0.205 g (1.26 mmol) of 1-phenyl-1, 2-propanedione 2-oxine and 0.211 g (1.26 mmol) of 4-phenylthiosemicarbazide were dissolved in 20 ml of methanol. One drop of sulfuric acid was added to catalyze the reaction. The resulting clear solution was refluxed for 12 h and there was a noticeable yellow color change. The reaction was removed from the heat and cooled to room temperature. The resulting yellow solution was transferred to a 125 ml separatory funnel. Dichloromethane (10 ml) and water (10 ml) were added, and the organic layer was separated. The aqueous layer was extracted with an additional 10 ml of dichloromethane, and then the organic layers were combined, washed with brine (2 x 10 ml), dried with magnesium sulfate, and the solvent was removed in vacuo to give a yellow solid. The product was recrystallized from hot acetonitrile. m.p. 463–464 K.
Crystal data, data collection and structure
details are summarizedin Table 1. A l l H atoms were located in difference maps. The C–H and N–H atoms were treated as riding atoms in geometrically idealized positions with C—H, N—H distances of 0.93 Å, 0.86 Å and refined with Uiso(H) = 1.2Ueq(C, N). The CH3 and O–H atoms were also treated as riding atoms in geometrically idealized positions with the CH3, O—H distances of 0.96 Å, 0.84 Å and refined with Uiso(H) = 1.5Ueq(C, O).Data collection: CrysAlis PRO (Agilent, 2014); cell
CrysAlis PRO (Agilent, 2014); data reduction: CrysAlis RED (Agilent, 2014); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL (Sheldrick, 2015b); molecular graphics: Olex2 (Dolomanov et al., 2009); software used to prepare material for publication: Olex2 (Dolomanov et al., 2009).Fig. 1. The molecular structure of C16H16N4OS, (I), showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level. The dashed line indicates a weak C11—H11···S1 intramolecular contact. | |
Fig. 2. Packing diagram of (I) viewed along the c axis. Dashed lines indicate O—H—N hydrogen bonds between the terminal hydroxy amino groups forming R22(6) inverson dimers stacked along [1 0 0]. The H atoms not involved in these interactions have been omitted for clarity. |
C16H16N4OS | F(000) = 656 |
Mr = 312.39 | Dx = 1.297 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 5.4955 (6) Å | Cell parameters from 4571 reflections |
b = 27.973 (2) Å | θ = 3.5–32.9° |
c = 10.4175 (9) Å | µ = 0.21 mm−1 |
β = 92.444 (9)° | T = 173 K |
V = 1600.0 (3) Å3 | Needle, colourless |
Z = 4 | 0.42 × 0.14 × 0.08 mm |
Agilent Eos, Gemini diffractometer | 5402 independent reflections |
Radiation source: Enhance (Mo) X-ray Source | 4006 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.044 |
Detector resolution: 16.0416 pixels mm-1 | θmax = 33.0°, θmin = 3.5° |
ω scans | h = −7→6 |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2014) | k = −39→42 |
Tmin = 0.747, Tmax = 1.000 | l = −14→15 |
17587 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)] = 0.065 | H-atom parameters constrained |
wR(F2) = 0.182 | w = 1/[σ2(Fo2) + (0.0835P)2 + 0.6623P] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max = 0.001 |
5402 reflections | Δρmax = 0.56 e Å−3 |
201 parameters | Δρmin = −0.37 e Å−3 |
0 restraints |
C16H16N4OS | V = 1600.0 (3) Å3 |
Mr = 312.39 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 5.4955 (6) Å | µ = 0.21 mm−1 |
b = 27.973 (2) Å | T = 173 K |
c = 10.4175 (9) Å | 0.42 × 0.14 × 0.08 mm |
β = 92.444 (9)° |
Agilent Eos, Gemini diffractometer | 5402 independent reflections |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2014) | 4006 reflections with I > 2σ(I) |
Tmin = 0.747, Tmax = 1.000 | Rint = 0.044 |
17587 measured reflections |
R[F2 > 2σ(F2)] = 0.065 | 0 restraints |
wR(F2) = 0.182 | H-atom parameters constrained |
S = 1.04 | Δρmax = 0.56 e Å−3 |
5402 reflections | Δρmin = −0.37 e Å−3 |
201 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
S1 | 0.45822 (11) | 0.63428 (2) | 0.03118 (5) | 0.04249 (17) | |
O1 | 1.5672 (3) | 0.55466 (5) | 0.56408 (13) | 0.0352 (3) | |
H1 | 1.6317 | 0.5292 | 0.5847 | 0.053* | |
N1 | 0.6605 (3) | 0.68290 (6) | 0.23282 (16) | 0.0396 (4) | |
H1A | 0.7732 | 0.6814 | 0.2925 | 0.047* | |
N2 | 0.8045 (3) | 0.60886 (5) | 0.19247 (14) | 0.0317 (3) | |
H2 | 0.8036 | 0.5826 | 0.1497 | 0.038* | |
N3 | 0.9654 (3) | 0.61454 (5) | 0.29421 (14) | 0.0292 (3) | |
N4 | 1.3985 (3) | 0.54711 (5) | 0.46248 (13) | 0.0261 (3) | |
C1 | 0.6445 (3) | 0.64429 (6) | 0.15726 (16) | 0.0283 (3) | |
C2 | 1.1020 (3) | 0.57835 (5) | 0.32323 (15) | 0.0248 (3) | |
C3 | 1.2802 (3) | 0.58508 (6) | 0.43056 (16) | 0.0275 (3) | |
C4 | 1.0875 (3) | 0.53131 (5) | 0.25667 (14) | 0.0234 (3) | |
C5 | 0.8957 (4) | 0.50060 (6) | 0.27837 (19) | 0.0351 (4) | |
H5 | 0.7749 | 0.5097 | 0.3333 | 0.042* | |
C6 | 0.8837 (4) | 0.45653 (7) | 0.2185 (2) | 0.0398 (4) | |
H6 | 0.7553 | 0.4359 | 0.2335 | 0.048* | |
C7 | 1.0618 (4) | 0.44308 (6) | 0.13634 (18) | 0.0327 (4) | |
H7 | 1.0540 | 0.4133 | 0.0968 | 0.039* | |
C8 | 1.2505 (4) | 0.47357 (7) | 0.11285 (18) | 0.0344 (4) | |
H8 | 1.3697 | 0.4645 | 0.0570 | 0.041* | |
C9 | 1.2637 (4) | 0.51787 (6) | 0.17228 (17) | 0.0311 (4) | |
H9 | 1.3908 | 0.5386 | 0.1556 | 0.037* | |
C10 | 0.5243 (4) | 0.72573 (6) | 0.23153 (18) | 0.0365 (4) | |
C11 | 0.3061 (6) | 0.73214 (9) | 0.1637 (3) | 0.0676 (9) | |
H11 | 0.2395 | 0.7075 | 0.1136 | 0.081* | |
C12 | 0.1862 (6) | 0.77580 (10) | 0.1708 (3) | 0.0749 (10) | |
H12 | 0.0384 | 0.7801 | 0.1256 | 0.090* | |
C13 | 0.2824 (6) | 0.81243 (9) | 0.2433 (3) | 0.0648 (8) | |
H13 | 0.2094 | 0.8424 | 0.2422 | 0.078* | |
C14 | 0.4845 (7) | 0.80392 (10) | 0.3160 (4) | 0.0897 (14) | |
H14 | 0.5435 | 0.8275 | 0.3721 | 0.108* | |
C15 | 0.6072 (6) | 0.76113 (9) | 0.3097 (3) | 0.0695 (10) | |
H15 | 0.7492 | 0.7566 | 0.3601 | 0.083* | |
C16 | 1.3123 (5) | 0.63254 (7) | 0.4947 (2) | 0.0491 (6) | |
H16A | 1.1963 | 0.6358 | 0.5605 | 0.074* | |
H16B | 1.2872 | 0.6575 | 0.4323 | 0.074* | |
H16C | 1.4743 | 0.6348 | 0.5325 | 0.074* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0480 (3) | 0.0359 (3) | 0.0417 (3) | 0.0114 (2) | −0.0199 (2) | −0.00529 (18) |
O1 | 0.0361 (7) | 0.0355 (7) | 0.0326 (6) | 0.0052 (5) | −0.0142 (5) | −0.0002 (5) |
N1 | 0.0474 (10) | 0.0274 (8) | 0.0420 (9) | 0.0158 (7) | −0.0197 (7) | −0.0071 (6) |
N2 | 0.0390 (9) | 0.0235 (7) | 0.0316 (7) | 0.0117 (6) | −0.0107 (6) | −0.0037 (5) |
N3 | 0.0349 (8) | 0.0248 (7) | 0.0272 (6) | 0.0086 (6) | −0.0069 (5) | −0.0020 (5) |
N4 | 0.0256 (7) | 0.0276 (7) | 0.0244 (6) | 0.0044 (5) | −0.0055 (5) | −0.0006 (5) |
C1 | 0.0322 (9) | 0.0226 (7) | 0.0297 (8) | 0.0055 (6) | −0.0040 (6) | 0.0024 (6) |
C2 | 0.0273 (8) | 0.0221 (7) | 0.0248 (7) | 0.0046 (6) | −0.0024 (6) | 0.0000 (5) |
C3 | 0.0311 (9) | 0.0240 (7) | 0.0271 (7) | 0.0032 (6) | −0.0035 (6) | −0.0012 (5) |
C4 | 0.0256 (8) | 0.0206 (7) | 0.0236 (7) | 0.0045 (5) | −0.0037 (5) | 0.0002 (5) |
C5 | 0.0335 (10) | 0.0273 (8) | 0.0453 (10) | 0.0007 (7) | 0.0102 (7) | −0.0021 (7) |
C6 | 0.0398 (11) | 0.0264 (9) | 0.0535 (11) | −0.0069 (7) | 0.0074 (9) | −0.0015 (8) |
C7 | 0.0405 (10) | 0.0221 (7) | 0.0349 (8) | 0.0011 (6) | −0.0036 (7) | −0.0030 (6) |
C8 | 0.0383 (10) | 0.0321 (9) | 0.0332 (8) | 0.0006 (7) | 0.0059 (7) | −0.0070 (6) |
C9 | 0.0320 (9) | 0.0286 (8) | 0.0332 (8) | −0.0041 (6) | 0.0059 (7) | −0.0051 (6) |
C10 | 0.0435 (11) | 0.0274 (8) | 0.0375 (9) | 0.0130 (7) | −0.0100 (8) | −0.0034 (6) |
C11 | 0.0659 (18) | 0.0420 (12) | 0.091 (2) | 0.0249 (12) | −0.0401 (15) | −0.0243 (12) |
C12 | 0.074 (2) | 0.0538 (15) | 0.093 (2) | 0.0350 (14) | −0.0419 (17) | −0.0214 (14) |
C13 | 0.078 (2) | 0.0420 (12) | 0.0712 (16) | 0.0336 (13) | −0.0279 (14) | −0.0210 (11) |
C14 | 0.103 (3) | 0.0505 (15) | 0.109 (3) | 0.0422 (16) | −0.066 (2) | −0.0462 (16) |
C15 | 0.078 (2) | 0.0453 (13) | 0.0806 (18) | 0.0310 (13) | −0.0487 (15) | −0.0319 (12) |
C16 | 0.0690 (16) | 0.0278 (9) | 0.0481 (12) | 0.0066 (9) | −0.0249 (11) | −0.0100 (8) |
S1—C1 | 1.6543 (18) | C7—H7 | 0.9300 |
O1—H1 | 0.8200 | C7—C8 | 1.373 (3) |
O1—N4 | 1.3930 (17) | C8—H8 | 0.9300 |
N1—H1A | 0.8600 | C8—C9 | 1.386 (2) |
N1—C1 | 1.337 (2) | C9—H9 | 0.9300 |
N1—C10 | 1.412 (2) | C10—C11 | 1.377 (3) |
N2—H2 | 0.8600 | C10—C15 | 1.349 (3) |
N2—N3 | 1.3604 (19) | C11—H11 | 0.9300 |
N2—C1 | 1.365 (2) | C11—C12 | 1.391 (3) |
N3—C2 | 1.288 (2) | C12—H12 | 0.9300 |
N4—C3 | 1.282 (2) | C12—C13 | 1.366 (4) |
C2—C3 | 1.467 (2) | C13—H13 | 0.9300 |
C2—C4 | 1.488 (2) | C13—C14 | 1.339 (4) |
C3—C16 | 1.493 (2) | C14—H14 | 0.9300 |
C4—C5 | 1.386 (2) | C14—C15 | 1.377 (3) |
C4—C9 | 1.387 (2) | C15—H15 | 0.9300 |
C5—H5 | 0.9300 | C16—H16A | 0.9600 |
C5—C6 | 1.382 (3) | C16—H16B | 0.9600 |
C6—H6 | 0.9300 | C16—H16C | 0.9600 |
C6—C7 | 1.379 (3) | ||
N4—O1—H1 | 109.5 | C7—C8—H8 | 120.0 |
C1—N1—H1A | 114.4 | C7—C8—C9 | 120.09 (18) |
C1—N1—C10 | 131.15 (15) | C9—C8—H8 | 120.0 |
C10—N1—H1A | 114.4 | C4—C9—H9 | 120.0 |
N3—N2—H2 | 119.5 | C8—C9—C4 | 120.06 (17) |
N3—N2—C1 | 120.97 (14) | C8—C9—H9 | 120.0 |
C1—N2—H2 | 119.5 | C11—C10—N1 | 124.38 (18) |
C2—N3—N2 | 116.34 (14) | C15—C10—N1 | 116.84 (18) |
C3—N4—O1 | 112.67 (13) | C15—C10—C11 | 118.60 (19) |
N1—C1—S1 | 128.83 (13) | C10—C11—H11 | 120.3 |
N1—C1—N2 | 113.76 (15) | C10—C11—C12 | 119.4 (2) |
N2—C1—S1 | 117.40 (13) | C12—C11—H11 | 120.3 |
N3—C2—C3 | 116.19 (14) | C11—C12—H12 | 119.5 |
N3—C2—C4 | 124.51 (14) | C13—C12—C11 | 121.0 (2) |
C3—C2—C4 | 119.30 (13) | C13—C12—H12 | 119.5 |
N4—C3—C2 | 113.98 (14) | C12—C13—H13 | 120.9 |
N4—C3—C16 | 124.84 (16) | C14—C13—C12 | 118.1 (2) |
C2—C3—C16 | 121.17 (15) | C14—C13—H13 | 120.9 |
C5—C4—C2 | 119.88 (15) | C13—C14—H14 | 119.2 |
C5—C4—C9 | 119.45 (15) | C13—C14—C15 | 121.6 (2) |
C9—C4—C2 | 120.67 (15) | C15—C14—H14 | 119.2 |
C4—C5—H5 | 120.0 | C10—C15—C14 | 120.9 (2) |
C6—C5—C4 | 120.09 (17) | C10—C15—H15 | 119.6 |
C6—C5—H5 | 120.0 | C14—C15—H15 | 119.6 |
C5—C6—H6 | 119.9 | C3—C16—H16A | 109.5 |
C7—C6—C5 | 120.12 (18) | C3—C16—H16B | 109.5 |
C7—C6—H6 | 119.9 | C3—C16—H16C | 109.5 |
C6—C7—H7 | 119.9 | H16A—C16—H16B | 109.5 |
C8—C7—C6 | 120.17 (16) | H16A—C16—H16C | 109.5 |
C8—C7—H7 | 119.9 | H16B—C16—H16C | 109.5 |
O1—N4—C3—C2 | 179.66 (14) | C3—C2—C4—C9 | −75.1 (2) |
O1—N4—C3—C16 | −0.9 (3) | C4—C2—C3—N4 | −4.6 (2) |
N1—C10—C11—C12 | 179.2 (3) | C4—C2—C3—C16 | 176.00 (19) |
N1—C10—C15—C14 | −179.2 (3) | C4—C5—C6—C7 | −0.4 (3) |
N2—N3—C2—C3 | 178.26 (15) | C5—C4—C9—C8 | −1.6 (3) |
N2—N3—C2—C4 | −2.4 (3) | C5—C6—C7—C8 | −0.6 (3) |
N3—N2—C1—S1 | 179.26 (14) | C6—C7—C8—C9 | 0.4 (3) |
N3—N2—C1—N1 | −1.4 (3) | C7—C8—C9—C4 | 0.7 (3) |
N3—C2—C3—N4 | 174.81 (16) | C9—C4—C5—C6 | 1.4 (3) |
N3—C2—C3—C16 | −4.6 (3) | C10—N1—C1—S1 | 1.7 (4) |
N3—C2—C4—C5 | −74.1 (2) | C10—N1—C1—N2 | −177.6 (2) |
N3—C2—C4—C9 | 105.6 (2) | C10—C11—C12—C13 | 0.4 (6) |
C1—N1—C10—C11 | 14.2 (4) | C11—C10—C15—C14 | −3.9 (5) |
C1—N1—C10—C15 | −170.8 (3) | C11—C12—C13—C14 | −5.6 (6) |
C1—N2—N3—C2 | 177.18 (17) | C12—C13—C14—C15 | 6.1 (7) |
C2—C4—C5—C6 | −178.89 (17) | C13—C14—C15—C10 | −1.4 (7) |
C2—C4—C9—C8 | 178.75 (16) | C15—C10—C11—C12 | 4.3 (5) |
C3—C2—C4—C5 | 105.27 (19) |
Cg1 is the centroid of the C4–C9 phenyl ring. |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···N4i | 0.82 | 2.20 | 2.867 (2) | 139 |
C5—H5···O1ii | 0.93 | 2.84 | 3.451 (3) | 124 |
C5—H5···N4ii | 0.93 | 2.85 | 3.472 (2) | 125 |
C6—H6···O1ii | 0.93 | 2.82 | 3.442 (3) | 125 |
C11—H11···S1 | 0.93 | 2.54 | 3.193 (2) | 127 |
O1—H1···Cg1i | 2.78 | 3.3309 (17) | 126 |
Symmetry codes: (i) −x+3, −y+1, −z+1; (ii) −x+2, −y+1, −z+1. |
Cg1 is the centroid of the C4–C9 phenyl ring. |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···N4i | 0.82 | 2.20 | 2.867 (2) | 139.3 |
C5—H5···O1ii | 0.93 | 2.84 | 3.451 (3) | 124.0 |
C5—H5···N4ii | 0.93 | 2.85 | 3.472 (2) | 125.3 |
C6—H6···O1ii | 0.93 | 2.82 | 3.442 (3) | 125.0 |
C11—H11···S1 | 0.93 | 2.54 | 3.193 (2) | 127.3 |
O1—H1···Cg1i | . | 2.78 | 3.3309 (17) | 126 |
Symmetry codes: (i) −x+3, −y+1, −z+1; (ii) −x+2, −y+1, −z+1. |
Acknowledgements
JPJ acknowledges the NSF–MRI program (grant No. CHE-1039027) for funds to purchase the X-ray diffractometer.
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In the title compound, C16H16N4OS, (I), one independent molecule crystallizes in the asymmetric unit and forms an intramolecular C11—H11···S1 hydrogen bond, (Fig. 1). With the exception of the C4···.C9 phenyl ring of the phenylpropylidene unit, the remainder of the molecule has an almost planar skeleton with an rms deviation of 0.121 (5) Å from the plane through the remaining 16 atoms. In the crystal O1—H1···N4 hydrogen bonds are observed between the terminal hydroxyimino groups forming inverson dimers with R22(6) graph-set motifs (Table 1) Additional C5—H5···N4 contacts stack the dimers along [1 0 0]. While no π–π interactions are present, weak C5—H5···O1, C6—H6···O1 and O1—H1···π interactions are also observed, and help stablize the crystal packing.