Crystal structure of 4-methyl­benzyl N′-[(thio­phen-2-yl)methyl­idene]hydrazinecarbodi­thio­ate

Ramli, S. binti; Ravoof, T.B.S.A.; Tahir, M.I.M.; Tiekink, E.R.T.

doi:10.1107/S205698901501107X

organic compounds

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ISSN: 2056-9890

Volume 71| Part 7| July 2015| Pages o475-o476

doi:10.1107/S205698901501107X

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Crystal structure of 4-methylbenzyl N′-[(thiophen-2-yl)methylidene]hydrazinecarbodithioate

Syahirah binti Ramli,^a ^* Thahira Begum S. A. Ravoof,^a ^* Mohamed Ibrahim Mohamed Tahir ^a and Edward R. T. Tiekink ^b

^aDepartment of Chemistry, Universiti Putra Malaysia, 43400 Serdang, Malaysia, and ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: thahira@upm.edu.my, thahira@upm.edu.my

Edited by W. T. A. Harrison, University of Aberdeen, Scotland (Received 3 June 2015; accepted 8 June 2015; online 13 June 2015)

In the title compound, C₁₅H₁₆N₂S₃ {systematic name: [({[(4-methylphenyl)methyl]sulfanyl}methanethioyl)amino][1-(thiophen-2-yl)ethylidene]amine}, the central CN₂S₂ residue is almost planar (r.m.s. deviation = 0.0061 Å) and forms dihedral angles of 7.39 (10) and 64.91 (5)° with the thienyl and p-tolyl rings, respectively; the dihedral angle between these rings is 57.52 (6)°. The non-thione S atoms are syn, and with respect to the thione S atom, the benzyl group is anti. In the crystal, centrosymmetrically related molecules self-associate via eight-membered {⋯HNCS}₂ synthons. The dimeric aggregates stack along the a axis and are are consolidated into a three-dimensional architecture via methyl-C—H⋯π(benzene) and benzene-C—H⋯π(thienyl) interactions.

Keywords: crystal structure; hydrogen bonding; dithiocarbazate; C—H⋯π interactions.

CCDC reference: 1405284

1. Related literature

For the structure of the parent compound, in which the benzyl residue is syn to the thione S atom, see: Chan et al. (2003 ). For the synthesis, see: Tarafder et al. (2002 ).

2. Experimental

2.1. Crystal data

C₁₅H₁₆N₂S₃
M_r = 320.48
Monoclinic, P 2₁ /c
a = 5.6956 (4) Å
b = 14.3424 (9) Å
c = 18.9255 (11) Å
β = 90.263 (5)°
V = 1545.98 (17) Å³
Z = 4
Cu Kα radiation
μ = 4.30 mm⁻¹
T = 150 K
0.15 × 0.10 × 0.06 mm

2.2. Data collection

Oxford Diffraction Xcaliber Eos Gemini diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ) T_min = 0.774, T_max = 1.000
8463 measured reflections
2830 independent reflections
2506 reflections with I > 2σ(I)
R_int = 0.023

2.3. Refinement

R[F² > 2σ(F²)] = 0.039
wR(F²) = 0.109
S = 1.06
2830 reflections
186 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.49 e Å⁻³
Δρ_min = −0.33 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the S3,C3–C6 and C8–C13 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯S2ⁱ	0.87 (2)	2.57 (2)	3.4433 (18)	176 (3)
C2′—H2′2⋯Cg2ⁱⁱ	0.98	2.85	3.616 (3)	138
C12—H12⋯Cg1ⁱⁱⁱ	0.95	2.89	3.560 (2)	130
Symmetry codes: (i) -x+1, -y+2, -z+1; (ii) $[x-1, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (iii) -x+1, -y+1, -z+1.

Data collection: CrysAlis PRO (Agilent, 2011); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2015 ); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ) and DIAMOND (Brandenburg, 2006 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

CCDC reference: 1405284

Crystal structure: contains datablocks 1, I. DOI: 10.1107/S205698901501107X/hb7439sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S205698901501107X/hb7439Isup2.hkl

checkCIF report

Related literature top

For the structure of the parent compound, in which the benzyl residue is syn to the thione S atom, see: Chan et al. (2003). For the synthesis, see: Tarafder et al. (2002).

Experimental top

The title compound was prepared as per a reported procedure (Tarafder et al., 2002). The light-yellow precipitate formed was filtered off and recrystallized from its acetonitrile solution as yellow prisms. Yield 56%; M.pt: 175–177 °C. Anal. Calcd for C₁₅H₁₆N₂S₃: C, 56.21; H, 5.03; N, 8.74. Found: C, 55.97; H, 4.96; N, 8.10. IR (cm^-1, FT—IR): 3143 w, 1511 m, 1060 m, 924 s. ¹H-NMR: (DMSO-d₆, p.p.m.) δ: 12.42 (s, 1H, NH), 7.24–7.55 (multiplet, 4H, Ar–H), 7.03–7.10 (multiplet, 3H, thiophene-H), 4.37 (s, 2H, –SCH₂), 2.24, 2.36 (s, 6H, –CH₃), 13 C-NMR:(DMSO-d₆, p.p.m.) δ: 197.98 (C=S), 159.15 (C=N), 129.32–142.86 (Ar–C), 128.39–129.90 (thiophene-C), 38.23 (SCH₂), 15.58, 21.24 (CH₃).

Computing details top

Data collection: CrysAlis PRO (Agilent, 2011); cell refinement: CrysAlis PRO (Agilent, 2011); data reduction: CrysAlis PRO (Agilent, 2011); program(s) used to solve structure: SHELXS97 (Sheldrick, 2015); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

	Fig. 1. The molecular structure of the title compound showing displacement ellipsoids at the 70% probability level.
	Fig. 2. Overlay diagram of the title compound (red image) with the parent compound (blue). The molecules have been overlapped so that the thienyl residues are coincident.
	Fig. 3. A view of the unit-cell contents in projection down the a axis. The N—H···S (orange) and C—H···π (purple) interactions are shown as dashed lines.

[({[(4-Methylphenyl)methyl]sulfanyl}methanethioyl)amino][1-(thiophen-2-yl)ethylidene]amine top

Crystal data top

C₁₅H₁₆N₂S₃	F(000) = 672
M_r = 320.48	D_x = 1.377 Mg m⁻³
Monoclinic, P2₁/c	Cu Kα radiation, λ = 1.54182 Å
a = 5.6956 (4) Å	Cell parameters from 3915 reflections
b = 14.3424 (9) Å	θ = 3.1–71.3°
c = 18.9255 (11) Å	µ = 4.30 mm⁻¹
β = 90.263 (5)°	T = 150 K
V = 1545.98 (17) Å³	Prism, yellow
Z = 4	0.15 × 0.10 × 0.06 mm

Data collection top

Oxford Diffraction Xcaliber Eos Gemini diffractometer	2830 independent reflections
Radiation source: fine-focus sealed tube	2506 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.023
Detector resolution: 16.1952 pixels mm^-1	θ_max = 71.3°, θ_min = 3.9°
ω scans	h = −6→6
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	k = −17→17
T_min = 0.774, T_max = 1.000	l = −16→22
8463 measured reflections

Refinement top

Refinement on F²	1 restraint
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.039	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.109	w = 1/[σ²(F_o²) + (0.0667P)² + 0.9619P] where P = (F_o² + 2F_c²)/3
S = 1.06	(Δ/σ)_max = 0.001
2830 reflections	Δρ_max = 0.49 e Å⁻³
186 parameters	Δρ_min = −0.33 e Å⁻³

Crystal data top

C₁₅H₁₆N₂S₃	V = 1545.98 (17) Å³
M_r = 320.48	Z = 4
Monoclinic, P2₁/c	Cu Kα radiation
a = 5.6956 (4) Å	µ = 4.30 mm⁻¹
b = 14.3424 (9) Å	T = 150 K
c = 18.9255 (11) Å	0.15 × 0.10 × 0.06 mm
β = 90.263 (5)°

Data collection top

Oxford Diffraction Xcaliber Eos Gemini diffractometer	2830 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	2506 reflections with I > 2σ(I)
T_min = 0.774, T_max = 1.000	R_int = 0.023
8463 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	1 restraint
wR(F²) = 0.109	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	Δρ_max = 0.49 e Å⁻³
2830 reflections	Δρ_min = −0.33 e Å⁻³
186 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.

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

	x	y	z	U_iso*/U_eq
S1	0.51174 (9)	0.72659 (3)	0.42082 (3)	0.01620 (16)
S2	0.71326 (10)	0.92093 (3)	0.43627 (3)	0.02009 (17)
S3	−0.06660 (10)	0.60844 (4)	0.53247 (3)	0.02183 (17)
N1	0.3513 (3)	0.85288 (12)	0.50603 (10)	0.0179 (4)
H1N	0.339 (5)	0.9097 (9)	0.5222 (13)	0.021*
N2	0.1971 (3)	0.78079 (12)	0.51907 (10)	0.0170 (4)
C1	0.5185 (4)	0.83886 (14)	0.45784 (12)	0.0171 (4)
C2	0.0454 (4)	0.79016 (15)	0.56846 (12)	0.0179 (5)
C2'	0.0181 (5)	0.87383 (16)	0.61556 (13)	0.0258 (5)
H2'1	0.1735	0.8977	0.6287	0.039*
H2'2	−0.0675	0.8559	0.6583	0.039*
H2'3	−0.0696	0.9224	0.5904	0.039*
C3	−0.1146 (4)	0.71133 (15)	0.57733 (12)	0.0174 (4)
C4	−0.3185 (4)	0.56050 (16)	0.56418 (13)	0.0237 (5)
H4	−0.3703	0.4993	0.5530	0.028*
C5	−0.4368 (4)	0.61936 (17)	0.60721 (13)	0.0243 (5)
H5	−0.5818	0.6033	0.6286	0.029*
C6	−0.3258 (4)	0.70718 (14)	0.61767 (12)	0.0175 (5)
H6	−0.3834	0.7557	0.6470	0.021*
C7	0.7561 (4)	0.73279 (15)	0.35948 (12)	0.0184 (5)
H7A	0.7341	0.7856	0.3265	0.022*
H7B	0.9052	0.7421	0.3856	0.022*
C8	0.7625 (4)	0.64185 (14)	0.31920 (11)	0.0165 (4)
C9	0.5788 (4)	0.61510 (15)	0.27450 (12)	0.0186 (5)
H9	0.4473	0.6551	0.2684	0.022*
C10	0.5867 (4)	0.53072 (15)	0.23898 (12)	0.0188 (5)
H10	0.4602	0.5136	0.2087	0.023*
C11	0.7773 (4)	0.47032 (15)	0.24688 (11)	0.0179 (5)
C11'	0.7835 (4)	0.37808 (16)	0.20945 (14)	0.0259 (5)
H11A	0.8516	0.3863	0.1624	0.039*
H11B	0.6235	0.3537	0.2048	0.039*
H11C	0.8795	0.3341	0.2367	0.039*
C12	0.9610 (4)	0.49777 (15)	0.29108 (12)	0.0179 (5)
H12	1.0934	0.4581	0.2968	0.022*
C13	0.9533 (4)	0.58213 (15)	0.32682 (12)	0.0177 (5)
H13	1.0800	0.5993	0.3569	0.021*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0185 (3)	0.0122 (3)	0.0180 (3)	−0.00068 (18)	0.0030 (2)	−0.00096 (18)
S2	0.0217 (3)	0.0135 (3)	0.0251 (3)	−0.0034 (2)	0.0057 (2)	−0.0019 (2)
S3	0.0233 (3)	0.0177 (3)	0.0244 (3)	−0.0018 (2)	−0.0013 (2)	−0.0007 (2)
N1	0.0208 (10)	0.0120 (8)	0.0209 (10)	−0.0019 (7)	0.0041 (8)	−0.0017 (7)
N2	0.0180 (9)	0.0139 (8)	0.0192 (9)	−0.0007 (7)	0.0008 (7)	0.0009 (7)
C1	0.0205 (11)	0.0131 (10)	0.0176 (11)	0.0012 (8)	−0.0015 (9)	−0.0002 (8)
C2	0.0188 (11)	0.0159 (10)	0.0190 (11)	0.0000 (8)	−0.0014 (9)	−0.0011 (8)
C2'	0.0298 (13)	0.0226 (11)	0.0251 (13)	−0.0066 (10)	0.0095 (10)	−0.0053 (10)
C3	0.0186 (11)	0.0169 (10)	0.0168 (11)	−0.0001 (8)	−0.0023 (9)	−0.0008 (8)
C4	0.0232 (12)	0.0205 (11)	0.0272 (13)	−0.0058 (9)	−0.0092 (10)	0.0064 (9)
C5	0.0185 (12)	0.0320 (13)	0.0225 (12)	−0.0039 (10)	−0.0024 (9)	0.0099 (10)
C6	0.0182 (11)	0.0146 (10)	0.0198 (11)	0.0005 (8)	−0.0076 (9)	0.0023 (8)
C7	0.0181 (11)	0.0168 (10)	0.0204 (11)	−0.0022 (8)	0.0061 (9)	−0.0006 (8)
C8	0.0178 (11)	0.0160 (10)	0.0157 (10)	−0.0023 (8)	0.0052 (8)	0.0008 (8)
C9	0.0169 (11)	0.0199 (10)	0.0190 (11)	0.0026 (8)	0.0012 (9)	0.0026 (8)
C10	0.0165 (11)	0.0230 (11)	0.0167 (11)	−0.0019 (9)	−0.0008 (9)	0.0002 (9)
C11	0.0194 (11)	0.0179 (10)	0.0164 (11)	−0.0014 (8)	0.0038 (9)	−0.0009 (8)
C11'	0.0259 (13)	0.0222 (11)	0.0296 (13)	0.0003 (9)	0.0008 (10)	−0.0073 (10)
C12	0.0161 (11)	0.0179 (10)	0.0198 (11)	0.0026 (8)	0.0003 (9)	0.0011 (8)
C13	0.0154 (11)	0.0203 (10)	0.0175 (11)	−0.0016 (8)	−0.0008 (9)	0.0003 (8)

Geometric parameters (Å, º) top

S1—C1	1.756 (2)	C6—H6	0.9500
S1—C7	1.818 (2)	C7—C8	1.511 (3)
S2—C1	1.670 (2)	C7—H7A	0.9900
S3—C4	1.703 (2)	C7—H7B	0.9900
S3—C3	1.725 (2)	C8—C13	1.391 (3)
N1—C1	1.337 (3)	C8—C9	1.396 (3)
N1—N2	1.379 (3)	C9—C10	1.385 (3)
N1—H1N	0.874 (10)	C9—H9	0.9500
N2—C2	1.283 (3)	C10—C11	1.396 (3)
C2—C3	1.462 (3)	C10—H10	0.9500
C2—C2'	1.503 (3)	C11—C12	1.393 (3)
C2'—H2'1	0.9800	C11—C11'	1.501 (3)
C2'—H2'2	0.9800	C11'—H11A	0.9800
C2'—H2'3	0.9800	C11'—H11B	0.9800
C3—C6	1.429 (3)	C11'—H11C	0.9800
C4—C5	1.354 (4)	C12—C13	1.387 (3)
C4—H4	0.9500	C12—H12	0.9500
C5—C6	1.423 (3)	C13—H13	0.9500
C5—H5	0.9500

C1—S1—C7	101.21 (10)	C8—C7—S1	107.47 (14)
C4—S3—C3	92.08 (12)	C8—C7—H7A	110.2
C1—N1—N2	117.73 (17)	S1—C7—H7A	110.2
C1—N1—H1N	115.8 (18)	C8—C7—H7B	110.2
N2—N1—H1N	125.9 (18)	S1—C7—H7B	110.2
C2—N2—N1	118.90 (18)	H7A—C7—H7B	108.5
N1—C1—S2	122.48 (16)	C13—C8—C9	118.5 (2)
N1—C1—S1	113.31 (16)	C13—C8—C7	120.0 (2)
S2—C1—S1	124.21 (14)	C9—C8—C7	121.5 (2)
N2—C2—C3	115.14 (19)	C10—C9—C8	120.5 (2)
N2—C2—C2'	126.0 (2)	C10—C9—H9	119.7
C3—C2—C2'	118.9 (2)	C8—C9—H9	119.7
C2—C2'—H2'1	109.5	C9—C10—C11	121.1 (2)
C2—C2'—H2'2	109.5	C9—C10—H10	119.4
H2'1—C2'—H2'2	109.5	C11—C10—H10	119.4
C2—C2'—H2'3	109.5	C12—C11—C10	118.0 (2)
H2'1—C2'—H2'3	109.5	C12—C11—C11'	120.9 (2)
H2'2—C2'—H2'3	109.5	C10—C11—C11'	121.1 (2)
C6—C3—C2	128.3 (2)	C11—C11'—H11A	109.5
C6—C3—S3	111.28 (16)	C11—C11'—H11B	109.5
C2—C3—S3	120.31 (17)	H11A—C11'—H11B	109.5
C5—C4—S3	112.48 (18)	C11—C11'—H11C	109.5
C5—C4—H4	123.8	H11A—C11'—H11C	109.5
S3—C4—H4	123.8	H11B—C11'—H11C	109.5
C4—C5—C6	114.4 (2)	C13—C12—C11	120.9 (2)
C4—C5—H5	122.8	C13—C12—H12	119.5
C6—C5—H5	122.8	C11—C12—H12	119.5
C5—C6—C3	109.7 (2)	C12—C13—C8	120.9 (2)
C5—C6—H6	125.1	C12—C13—H13	119.6
C3—C6—H6	125.1	C8—C13—H13	119.6

C1—N1—N2—C2	175.2 (2)	C2—C3—C6—C5	175.4 (2)
N2—N1—C1—S2	179.03 (15)	S3—C3—C6—C5	−1.4 (2)
N2—N1—C1—S1	−1.3 (3)	C1—S1—C7—C8	−176.13 (15)
C7—S1—C1—N1	179.94 (17)	S1—C7—C8—C13	−115.3 (2)
C7—S1—C1—S2	−0.39 (17)	S1—C7—C8—C9	63.9 (2)
N1—N2—C2—C3	178.49 (18)	C13—C8—C9—C10	0.3 (3)
N1—N2—C2—C2'	−0.5 (3)	C7—C8—C9—C10	−178.9 (2)
N2—C2—C3—C6	−167.3 (2)	C8—C9—C10—C11	0.1 (3)
C2'—C2—C3—C6	11.7 (3)	C9—C10—C11—C12	−0.6 (3)
N2—C2—C3—S3	9.2 (3)	C9—C10—C11—C11'	178.8 (2)
C2'—C2—C3—S3	−171.73 (17)	C10—C11—C12—C13	0.7 (3)
C4—S3—C3—C6	0.80 (17)	C11'—C11—C12—C13	−178.7 (2)
C4—S3—C3—C2	−176.29 (18)	C11—C12—C13—C8	−0.3 (3)
C3—S3—C4—C5	0.04 (19)	C9—C8—C13—C12	−0.2 (3)
S3—C4—C5—C6	−0.9 (3)	C7—C8—C13—C12	179.1 (2)
C4—C5—C6—C3	1.5 (3)

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of the S3,C3–C6 and C8–C13 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···S2ⁱ	0.87 (2)	2.57 (2)	3.4433 (18)	176 (3)
C2′—H2′2···Cg2ⁱⁱ	0.98	2.85	3.616 (3)	138
C12—H12···Cg1ⁱⁱⁱ	0.95	2.89	3.560 (2)	130

Symmetry codes: (i) −x+1, −y+2, −z+1; (ii) x−1, −y+1/2, z−1/2; (iii) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of the S3,C3–C6 and C8–C13 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···S2ⁱ	0.874 (15)	2.571 (15)	3.4433 (18)	176 (3)
C2'—H2'2···Cg2ⁱⁱ	0.98	2.85	3.616 (3)	138
C12—H12···Cg1ⁱⁱⁱ	0.95	2.89	3.560 (2)	130

Symmetry codes: (i) −x+1, −y+2, −z+1; (ii) x−1, −y+1/2, z−1/2; (iii) −x+1, −y+1, −z+1.

Acknowledgements

The research was funded by Universiti Putra Malaysia (UPM) under Research University Grant Schemes (RUGS No. 9419400), the Fundamental Research Grant Scheme (FRGS No. 5524425) and the Science Fund (Science Fund No. 06-01-04-SF810). SR thanks the UPM for the award of a Graduate Research Fellowship.

References

Agilent (2011). CrysAlis PRO. Agilent Technologies, Yarnton, England. Google Scholar
Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Chan, M.-H. E., Crouse, K. A., Tarafder, M. T. H. & Yamin, B. M. (2003). Acta Cryst. E59, o628–o629. Web of Science CSD CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2015). Acta Cryst. C71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Tarafder, M. T. H., Khoo, T.-J., Crouse, K. A., Ali, A. M., Yamin, B. M. & Fun, H.-K. (2002). Polyhedron, 21, 2691–2698. Web of Science CSD CrossRef CAS Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar

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ISSN: 2056-9890

Volume 71| Part 7| July 2015| Pages o475-o476

doi:10.1107/S205698901501107X

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

Crystal structure of 4-methyl­benzyl N′-[(thio­phen-2-yl)methyl­­idene]hydrazinecarbodi­thio­ate

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 4-methylbenzyl N′-[(thiophen-2-yl)methylidene]hydrazinecarbodithioate