organic compounds
E)-2-[(4-chloro-2H-chromen-3-yl)methylidene]-N-cyclohexylhydrazinecarbothioamide
of (aDepartment of Physics, Ethiraj College for Women (Autonomous), Chennai 600 008, India, bDepartment of Chemistry, National Institute of Technology, Tiruchirappalli 620 015, India, and cDepartment of Physics, RKM Vivekananda College (Autonomous), Chennai 600 004, India
*Correspondence e-mail: ksethusankar@yahoo.co.in
In the title compound, C17H20ClN3OS, the mean plane of the central thiourea core makes dihedral angles of 26.56 (9) and 47.62 (12)° with the mean planes of the chromene moiety and the cyclohexyl ring, respectively. The cyclohexyl ring adopts a chair conformation. The N–H atoms of the thiourea unit adopt an anti conformation. The chromene group is positioned trans, whereas the cyclohexyl ring lies in the cis position to the thione S atom, with respect to the thiourea C—N bond. In the crystal, molecules are linked by N—H⋯S hydrogen bonds, forming inversion dimers enclosing R22(8) ring motifs. The dimers are linked by C—H⋯Cl hydrogen bonds, enclosing R66(44) ring motifs, forming sheets lying parallel to (010).
Keywords: crystal structure; chromene; hydrazine; thioamide; cyclohexyl; hydrogen bonds.
CCDC reference: 1016441
1. Related literature
For the biological properties of thiosemicarbazones, see: Prabhakaran et al. (2007); Kelly et al. (1996); West et al. (1993); Pérez et al. (1999). For their optical properties and applications, see: Tian et al. (1997); Uesugi et al. (1994). For a related structure, see: Jayakumar et al. (2011).
2. Experimental
2.1. Crystal data
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2.3. Refinement
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Data collection: APEX2 (Bruker, 2008); cell 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: 1016441
10.1107/S1600536814018509/su2769sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536814018509/su2769Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536814018509/su2769Isup3.cml
An ethanol solution of N-cyclohexylhydrazinecarbothioamide (1.736 g, 0.01 mole) was added to a ethanol solution (50 cm3) of 4-chloro-2H-chromene-3-carbaldehyde (1.94 g, 0.01 mole). The mixture was refluxed for 2 h during which time a yellow precipitate separated out. The reaction mixture was then cooled to room temperature and the precipitate was filtered off. It was then washed with ethanol and dried under vacuum (Yield: 85%). Crystals of the title compound were obtained by slow evaporation of a solution in ethanol.
The positions of the H atoms were localized from difference electron density maps and they were refined as riding atoms: N-H = 0.86 Å, C-H = 0.93 - 0.98 Å, with Uiso(H) = 1.5Ueq(C-methyl) and = 1.2Ueq(N,C) for other H atoms.
Data collection: APEX2 (Bruker, 2008); cell
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).C17H20ClN3OS | F(000) = 1472 |
Mr = 349.87 | Dx = 1.334 Mg m−3 |
Orthorhombic, Pbca | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ac 2ab | Cell parameters from 2762 reflections |
a = 12.2857 (12) Å | θ = 2.2–28.3° |
b = 15.3082 (16) Å | µ = 0.35 mm−1 |
c = 18.5241 (18) Å | T = 296 K |
V = 3483.9 (6) Å3 | Block, colourless |
Z = 8 | 0.30 × 0.25 × 0.20 mm |
Bruker SMART APEXII area-detector diffractometer | 4291 independent reflections |
Radiation source: fine-focus sealed tube | 2762 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.033 |
ω and ϕ scans | θmax = 28.3°, θmin = 2.2° |
Absorption correction: multi-scan (SADABS; Bruker, 2008) | h = −15→16 |
Tmin = 0.901, Tmax = 0.933 | k = −19→19 |
18568 measured reflections | l = −24→23 |
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)] = 0.050 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.152 | H-atom parameters constrained |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0745P)2 + 0.9377P] where P = (Fo2 + 2Fc2)/3 |
4291 reflections | (Δ/σ)max = 0.001 |
208 parameters | Δρmax = 0.32 e Å−3 |
0 restraints | Δρmin = −0.31 e Å−3 |
C17H20ClN3OS | V = 3483.9 (6) Å3 |
Mr = 349.87 | Z = 8 |
Orthorhombic, Pbca | Mo Kα radiation |
a = 12.2857 (12) Å | µ = 0.35 mm−1 |
b = 15.3082 (16) Å | T = 296 K |
c = 18.5241 (18) Å | 0.30 × 0.25 × 0.20 mm |
Bruker SMART APEXII area-detector diffractometer | 4291 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2008) | 2762 reflections with I > 2σ(I) |
Tmin = 0.901, Tmax = 0.933 | Rint = 0.033 |
18568 measured reflections |
R[F2 > 2σ(F2)] = 0.050 | 0 restraints |
wR(F2) = 0.152 | H-atom parameters constrained |
S = 1.02 | Δρmax = 0.32 e Å−3 |
4291 reflections | Δρmin = −0.31 e Å−3 |
208 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. |
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. |
x | y | z | Uiso*/Ueq | ||
C1 | 1.1410 (2) | 0.0421 (2) | 0.35313 (15) | 0.0735 (8) | |
H1 | 1.1134 | 0.0105 | 0.3144 | 0.088* | |
C2 | 1.2530 (2) | 0.0541 (2) | 0.36038 (19) | 0.0835 (10) | |
H2 | 1.2997 | 0.0306 | 0.3259 | 0.100* | |
C3 | 1.2948 (2) | 0.0990 (2) | 0.41635 (19) | 0.0824 (9) | |
H3 | 1.3698 | 0.1057 | 0.4205 | 0.099* | |
C4 | 1.2276 (2) | 0.1348 (2) | 0.46699 (17) | 0.0790 (8) | |
H4 | 1.2568 | 0.1662 | 0.5054 | 0.095* | |
C5 | 1.11588 (18) | 0.12440 (18) | 0.46109 (13) | 0.0600 (6) | |
C6 | 1.07055 (17) | 0.07780 (15) | 0.40441 (12) | 0.0514 (5) | |
C7 | 0.95198 (17) | 0.06950 (15) | 0.40340 (11) | 0.0485 (5) | |
C8 | 0.88960 (16) | 0.10411 (14) | 0.45507 (10) | 0.0438 (5) | |
C9 | 0.94477 (19) | 0.1572 (2) | 0.51200 (14) | 0.0712 (8) | |
H9A | 0.9170 | 0.2164 | 0.5085 | 0.085* | |
H9B | 0.9222 | 0.1345 | 0.5585 | 0.085* | |
C10 | 0.77399 (16) | 0.08929 (15) | 0.46230 (10) | 0.0453 (5) | |
H10 | 0.7364 | 0.0579 | 0.4273 | 0.054* | |
C11 | 0.56710 (15) | 0.10953 (15) | 0.58999 (10) | 0.0444 (5) | |
C12 | 0.59224 (15) | 0.17836 (15) | 0.71073 (10) | 0.0423 (5) | |
H12 | 0.5665 | 0.1240 | 0.7327 | 0.051* | |
C13 | 0.50398 (19) | 0.24676 (16) | 0.71814 (12) | 0.0563 (6) | |
H13A | 0.4375 | 0.2255 | 0.6960 | 0.068* | |
H13B | 0.5259 | 0.2995 | 0.6930 | 0.068* | |
C14 | 0.4829 (2) | 0.2677 (2) | 0.79728 (14) | 0.0729 (8) | |
H14A | 0.4279 | 0.3129 | 0.8007 | 0.087* | |
H14B | 0.4555 | 0.2160 | 0.8215 | 0.087* | |
C15 | 0.5855 (2) | 0.2981 (2) | 0.83439 (14) | 0.0733 (8) | |
H15A | 0.6093 | 0.3527 | 0.8130 | 0.088* | |
H15B | 0.5704 | 0.3087 | 0.8850 | 0.088* | |
C16 | 0.6747 (2) | 0.2314 (2) | 0.82767 (13) | 0.0713 (8) | |
H16A | 0.6547 | 0.1794 | 0.8546 | 0.086* | |
H16B | 0.7410 | 0.2546 | 0.8486 | 0.086* | |
C17 | 0.69562 (17) | 0.2068 (2) | 0.74917 (12) | 0.0645 (7) | |
H17A | 0.7266 | 0.2566 | 0.7241 | 0.077* | |
H17B | 0.7483 | 0.1597 | 0.7474 | 0.077* | |
N1 | 0.72378 (13) | 0.11972 (13) | 0.51739 (8) | 0.0456 (4) | |
N2 | 0.61712 (13) | 0.09549 (13) | 0.52482 (8) | 0.0481 (4) | |
H2A | 0.5823 | 0.0721 | 0.4895 | 0.058* | |
N3 | 0.62011 (13) | 0.16098 (12) | 0.63520 (9) | 0.0486 (4) | |
H3A | 0.6769 | 0.1870 | 0.6185 | 0.058* | |
Cl1 | 0.89480 (7) | 0.01105 (6) | 0.33357 (4) | 0.0936 (3) | |
O1 | 1.05307 (15) | 0.16182 (18) | 0.51223 (12) | 0.1067 (9) | |
S1 | 0.44825 (4) | 0.05982 (5) | 0.60746 (3) | 0.0645 (2) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0760 (17) | 0.0745 (19) | 0.0699 (15) | 0.0181 (15) | 0.0253 (13) | 0.0081 (14) |
C2 | 0.0698 (17) | 0.086 (2) | 0.095 (2) | 0.0314 (16) | 0.0410 (16) | 0.0311 (19) |
C3 | 0.0520 (14) | 0.089 (2) | 0.106 (2) | 0.0117 (15) | 0.0193 (15) | 0.039 (2) |
C4 | 0.0504 (13) | 0.093 (2) | 0.0933 (19) | −0.0055 (14) | 0.0029 (13) | 0.0141 (18) |
C5 | 0.0483 (12) | 0.0669 (16) | 0.0649 (13) | −0.0009 (12) | 0.0085 (10) | 0.0079 (13) |
C6 | 0.0532 (11) | 0.0488 (13) | 0.0523 (11) | 0.0072 (10) | 0.0149 (9) | 0.0133 (10) |
C7 | 0.0581 (12) | 0.0446 (12) | 0.0429 (10) | −0.0022 (10) | 0.0071 (9) | −0.0021 (9) |
C8 | 0.0481 (10) | 0.0453 (12) | 0.0381 (9) | −0.0035 (9) | 0.0032 (8) | 0.0006 (9) |
C9 | 0.0466 (12) | 0.100 (2) | 0.0675 (15) | −0.0087 (13) | 0.0033 (10) | −0.0310 (15) |
C10 | 0.0467 (10) | 0.0522 (13) | 0.0370 (9) | −0.0054 (10) | 0.0004 (8) | −0.0019 (9) |
C11 | 0.0390 (9) | 0.0516 (13) | 0.0425 (9) | 0.0002 (9) | 0.0007 (7) | −0.0016 (10) |
C12 | 0.0405 (9) | 0.0481 (12) | 0.0385 (9) | −0.0048 (9) | 0.0027 (7) | −0.0014 (9) |
C13 | 0.0556 (13) | 0.0614 (16) | 0.0519 (11) | 0.0092 (12) | 0.0019 (9) | −0.0019 (11) |
C14 | 0.0633 (15) | 0.092 (2) | 0.0634 (14) | 0.0143 (15) | 0.0081 (12) | −0.0221 (15) |
C15 | 0.0829 (18) | 0.0764 (19) | 0.0608 (14) | −0.0063 (16) | 0.0083 (13) | −0.0251 (14) |
C16 | 0.0611 (14) | 0.097 (2) | 0.0556 (13) | −0.0050 (15) | −0.0097 (11) | −0.0245 (14) |
C17 | 0.0412 (11) | 0.0898 (19) | 0.0625 (13) | −0.0023 (12) | −0.0016 (10) | −0.0232 (14) |
N1 | 0.0417 (8) | 0.0540 (11) | 0.0412 (8) | −0.0050 (8) | 0.0034 (6) | 0.0009 (8) |
N2 | 0.0396 (8) | 0.0637 (12) | 0.0410 (8) | −0.0071 (8) | 0.0016 (6) | −0.0058 (8) |
N3 | 0.0423 (8) | 0.0598 (12) | 0.0436 (8) | −0.0144 (8) | 0.0096 (7) | −0.0081 (8) |
Cl1 | 0.0938 (6) | 0.1186 (7) | 0.0683 (4) | −0.0167 (5) | 0.0133 (3) | −0.0505 (4) |
O1 | 0.0485 (10) | 0.173 (3) | 0.0992 (15) | −0.0152 (12) | 0.0062 (9) | −0.0721 (16) |
S1 | 0.0446 (3) | 0.0870 (5) | 0.0621 (4) | −0.0208 (3) | 0.0102 (2) | −0.0205 (3) |
C1—C2 | 1.395 (4) | C11—S1 | 1.678 (2) |
C1—C6 | 1.397 (3) | C12—N3 | 1.465 (2) |
C1—H1 | 0.9300 | C12—C13 | 1.514 (3) |
C2—C3 | 1.346 (5) | C12—C17 | 1.520 (3) |
C2—H2 | 0.9300 | C12—H12 | 0.9800 |
C3—C4 | 1.364 (4) | C13—C14 | 1.523 (3) |
C3—H3 | 0.9300 | C13—H13A | 0.9700 |
C4—C5 | 1.387 (3) | C13—H13B | 0.9700 |
C4—H4 | 0.9300 | C14—C15 | 1.510 (4) |
C5—O1 | 1.349 (3) | C14—H14A | 0.9700 |
C5—C6 | 1.386 (3) | C14—H14B | 0.9700 |
C6—C7 | 1.462 (3) | C15—C16 | 1.503 (4) |
C7—C8 | 1.336 (3) | C15—H15A | 0.9700 |
C7—Cl1 | 1.723 (2) | C15—H15B | 0.9700 |
C8—C10 | 1.445 (3) | C16—C17 | 1.524 (3) |
C8—C9 | 1.494 (3) | C16—H16A | 0.9700 |
C9—O1 | 1.332 (3) | C16—H16B | 0.9700 |
C9—H9A | 0.9700 | C17—H17A | 0.9700 |
C9—H9B | 0.9700 | C17—H17B | 0.9700 |
C10—N1 | 1.280 (3) | N1—N2 | 1.369 (2) |
C10—H10 | 0.9300 | N2—H2A | 0.8600 |
C11—N3 | 1.321 (3) | N3—H3A | 0.8600 |
C11—N2 | 1.372 (2) | ||
C2—C1—C6 | 119.7 (3) | C13—C12—H12 | 108.6 |
C2—C1—H1 | 120.2 | C17—C12—H12 | 108.6 |
C6—C1—H1 | 120.2 | C12—C13—C14 | 110.75 (19) |
C3—C2—C1 | 121.2 (3) | C12—C13—H13A | 109.5 |
C3—C2—H2 | 119.4 | C14—C13—H13A | 109.5 |
C1—C2—H2 | 119.4 | C12—C13—H13B | 109.5 |
C2—C3—C4 | 120.3 (3) | C14—C13—H13B | 109.5 |
C2—C3—H3 | 119.9 | H13A—C13—H13B | 108.1 |
C4—C3—H3 | 119.9 | C15—C14—C13 | 111.2 (2) |
C3—C4—C5 | 119.9 (3) | C15—C14—H14A | 109.4 |
C3—C4—H4 | 120.0 | C13—C14—H14A | 109.4 |
C5—C4—H4 | 120.0 | C15—C14—H14B | 109.4 |
O1—C5—C6 | 121.4 (2) | C13—C14—H14B | 109.4 |
O1—C5—C4 | 117.5 (3) | H14A—C14—H14B | 108.0 |
C6—C5—C4 | 121.1 (2) | C16—C15—C14 | 111.2 (2) |
C5—C6—C1 | 117.9 (2) | C16—C15—H15A | 109.4 |
C5—C6—C7 | 117.04 (19) | C14—C15—H15A | 109.4 |
C1—C6—C7 | 125.1 (2) | C16—C15—H15B | 109.4 |
C8—C7—C6 | 121.9 (2) | C14—C15—H15B | 109.4 |
C8—C7—Cl1 | 120.68 (17) | H15A—C15—H15B | 108.0 |
C6—C7—Cl1 | 117.45 (16) | C15—C16—C17 | 111.7 (2) |
C7—C8—C10 | 124.63 (19) | C15—C16—H16A | 109.3 |
C7—C8—C9 | 117.47 (19) | C17—C16—H16A | 109.3 |
C10—C8—C9 | 117.78 (18) | C15—C16—H16B | 109.3 |
O1—C9—C8 | 119.0 (2) | C17—C16—H16B | 109.3 |
O1—C9—H9A | 107.6 | H16A—C16—H16B | 107.9 |
C8—C9—H9A | 107.6 | C12—C17—C16 | 112.15 (18) |
O1—C9—H9B | 107.6 | C12—C17—H17A | 109.2 |
C8—C9—H9B | 107.6 | C16—C17—H17A | 109.2 |
H9A—C9—H9B | 107.0 | C12—C17—H17B | 109.2 |
N1—C10—C8 | 119.37 (18) | C16—C17—H17B | 109.2 |
N1—C10—H10 | 120.3 | H17A—C17—H17B | 107.9 |
C8—C10—H10 | 120.3 | C10—N1—N2 | 116.28 (17) |
N3—C11—N2 | 115.49 (17) | N1—N2—C11 | 118.36 (16) |
N3—C11—S1 | 125.24 (15) | N1—N2—H2A | 120.8 |
N2—C11—S1 | 119.25 (15) | C11—N2—H2A | 120.8 |
N3—C12—C13 | 112.32 (17) | C11—N3—C12 | 126.76 (17) |
N3—C12—C17 | 107.71 (16) | C11—N3—H3A | 116.6 |
C13—C12—C17 | 110.98 (19) | C12—N3—H3A | 116.6 |
N3—C12—H12 | 108.6 | C9—O1—C5 | 123.1 (2) |
C6—C1—C2—C3 | 0.5 (4) | C7—C8—C10—N1 | 174.1 (2) |
C1—C2—C3—C4 | −0.7 (5) | C9—C8—C10—N1 | −1.8 (3) |
C2—C3—C4—C5 | 0.4 (5) | N3—C12—C13—C14 | −176.0 (2) |
C3—C4—C5—O1 | −179.4 (3) | C17—C12—C13—C14 | −55.4 (3) |
C3—C4—C5—C6 | 0.1 (4) | C12—C13—C14—C15 | 57.3 (3) |
O1—C5—C6—C1 | 179.1 (3) | C13—C14—C15—C16 | −56.7 (3) |
C4—C5—C6—C1 | −0.4 (4) | C14—C15—C16—C17 | 54.5 (3) |
O1—C5—C6—C7 | −1.3 (4) | N3—C12—C17—C16 | 176.9 (2) |
C4—C5—C6—C7 | 179.3 (2) | C13—C12—C17—C16 | 53.6 (3) |
C2—C1—C6—C5 | 0.1 (4) | C15—C16—C17—C12 | −53.2 (3) |
C2—C1—C6—C7 | −179.5 (2) | C8—C10—N1—N2 | −173.26 (19) |
C5—C6—C7—C8 | −0.8 (3) | C10—N1—N2—C11 | 165.58 (19) |
C1—C6—C7—C8 | 178.8 (2) | N3—C11—N2—N1 | 13.0 (3) |
C5—C6—C7—Cl1 | −179.54 (18) | S1—C11—N2—N1 | −165.46 (16) |
C1—C6—C7—Cl1 | 0.1 (3) | N2—C11—N3—C12 | −172.13 (19) |
C6—C7—C8—C10 | −171.9 (2) | S1—C11—N3—C12 | 6.2 (3) |
Cl1—C7—C8—C10 | 6.7 (3) | C13—C12—N3—C11 | −81.4 (3) |
C6—C7—C8—C9 | 4.0 (3) | C17—C12—N3—C11 | 156.1 (2) |
Cl1—C7—C8—C9 | −177.36 (19) | C8—C9—O1—C5 | 3.6 (5) |
C7—C8—C9—O1 | −5.4 (4) | C6—C5—O1—C9 | −0.3 (5) |
C10—C8—C9—O1 | 170.8 (3) | C4—C5—O1—C9 | 179.2 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2A···S1i | 0.86 | 2.73 | 3.507 (2) | 151 |
C12—H12···Cl1ii | 0.98 | 2.83 | 3.689 (2) | 147 |
Symmetry codes: (i) −x+1, −y, −z+1; (ii) −x+3/2, −y, z+1/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2A···S1i | 0.86 | 2.73 | 3.507 (2) | 151 |
C12—H12···Cl1ii | 0.98 | 2.83 | 3.689 (2) | 147 |
Symmetry codes: (i) −x+1, −y, −z+1; (ii) −x+3/2, −y, z+1/2. |
Acknowledgements
The authors thank Professors D. Velmurugan and T. Srinivasan of the Centre for Advanced Study in Crystallography and Biophysics, University of Madras, Chennai, India, for the data collection.
References
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