Crystal structure of (E)-2-[(4-chloro-2H-chromen-3-yl)methyl­idene]-N-cyclo­hexyl­hydrazinecarbo­thio­amide

Gangadharan, R.; Haribabu, J.; Karvembu, R.; Sethusankar, K.

doi:10.1107/S1600536814018509

organic compounds

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ISSN: 2056-9890

Volume 70| Part 9| September 2014| Pages o1039-o1040

doi:10.1107/S1600536814018509

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Crystal structure of (E)-2-[(4-chloro-2H-chromen-3-yl)methylidene]-N-cyclohexylhydrazinecarbothioamide

Rajeswari Gangadharan,^a Jebiti Haribabu,^b Ramasamy Karvembu ^b and K. Sethusankar ^c ^*

^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

Edited by H. Stoeckli-Evans, University of Neuchâtel, Switzerland (Received 7 August 2014; accepted 14 August 2014; online 23 August 2014)

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

C₁₇H₂₀ClN₃OS
M_r = 349.87
Orthorhombic, P b c a
a = 12.2857 (12) Å
b = 15.3082 (16) Å
c = 18.5241 (18) Å
V = 3483.9 (6) Å³
Z = 8
Mo Kα radiation
μ = 0.35 mm⁻¹
T = 296 K
0.30 × 0.25 × 0.20 mm

2.2. Data collection

Bruker SMART APEXII area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2008 ) T_min = 0.901, T_max = 0.933
18568 measured reflections
4291 independent reflections
2762 reflections with I > 2σ(I)
R_int = 0.033

2.3. Refinement

R[F² > 2σ(F²)] = 0.050
wR(F²) = 0.152
S = 1.02
4291 reflections
208 parameters
H-atom parameters constrained
Δρ_max = 0.32 e Å⁻³
Δρ_min = −0.31 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

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) $[-x+{\script{3\over 2}}, -y, z+{\script{1\over 2}}]$ .

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: 1016441

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536814018509/su2769sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814018509/su2769Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536814018509/su2769Isup3.cml

checkCIF report

Related literature top

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).

Experimental top

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.

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 molecule, with atom labelling. The displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. The crystal packing of the title compound viewed along the a axis. The hydrogen bonds are shown as dashed lines (see Table 1 for details; H atoms not involved in hydrogen bonding have been omitted for clarity).

(E)-2-[(4-Chloro-2H-chromen-3-yl)methylidene]-N-cyclohexylhydrazine carbothioamide top

Crystal data top

C₁₇H₂₀ClN₃OS	F(000) = 1472
M_r = 349.87	D_x = 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

Data collection top

Bruker SMART APEXII area-detector diffractometer	4291 independent reflections
Radiation source: fine-focus sealed tube	2762 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.033
ω and ϕ scans	θ_max = 28.3°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −15→16
T_min = 0.901, T_max = 0.933	k = −19→19
18568 measured reflections	l = −24→23

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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.152	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0745P)² + 0.9377P] where P = (F_o² + 2F_c²)/3
4291 reflections	(Δ/σ)_max = 0.001
208 parameters	Δρ_max = 0.32 e Å⁻³
0 restraints	Δρ_min = −0.31 e Å⁻³

Crystal data top

C₁₇H₂₀ClN₃OS	V = 3483.9 (6) Å³
M_r = 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

Data collection top

Bruker SMART APEXII area-detector diffractometer	4291 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2008)	2762 reflections with I > 2σ(I)
T_min = 0.901, T_max = 0.933	R_int = 0.033
18568 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.050	0 restraints
wR(F²) = 0.152	H-atom parameters constrained
S = 1.02	Δρ_max = 0.32 e Å⁻³
4291 reflections	Δρ_min = −0.31 e Å⁻³
208 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	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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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.

Hydrogen-bond geometry (Å, º) top

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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Volume 70| Part 9| September 2014| Pages o1039-o1040

doi:10.1107/S1600536814018509

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

Crystal structure of (E)-2-[(4-chloro-2H-chromen-3-yl)methyl­­idene]-N-cyclo­hexyl­hydrazinecarbo­thio­amide

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 (E)-2-[(4-chloro-2H-chromen-3-yl)methylidene]-N-cyclohexylhydrazinecarbothioamide