(Z)-N,N-Dimethyl-2-[phen­yl(pyridin-2-yl)methyl­idene]hydrazinecarbothio­amide

Jayakumar, K.; Sithambaresan, M.; Prathapachandra Kurup, M.R.

doi:10.1107/S1600536811045739

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 67| Part 12| December 2011| Page o3195

https://doi.org/10.1107/S1600536811045739

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(Z)-N,N-Dimethyl-2-[phenyl(pyridin-2-yl)methylidene]hydrazinecarbothioamide

K. Jayakumar,^a M. Sithambaresan ^b ^* and M. R. Prathapachandra Kurup ^a

^aDepartment of Applied Chemistry, Cochin University of Science and Technology, Kochi 682 022, India, and ^bDepartment of Chemistry, Faculty of Science, Eastern University, Sri Lanka, Chenkalady, Sri Lanka
^*Correspondence e-mail: eesans@yahoo.com

(Received 5 October 2011; accepted 31 October 2011; online 5 November 2011)

The title compound, C₁₅H₁₆N₄S, exists in the Z conformation with the thionyl S atom lying cis to the azomethine N atom. The shortening of the N—N distance [1.3697 (17) Å] is due to extensive delocalization with the pyridine ring. The hydrazine–carbothioamide unit is almost planar, with a maximum deviation of 0.013 (2) Å for the amide N atom. The stability of this conformation is favoured by the formation of an intramolecular N—H⋯N hydrogen bond. The packing of the molecules involves no classical intermolecular hydrogen-bonding interactions; however, a C—H⋯π interaction occurs.

Related literature

For abackground to hydrazinecarbothioamide and its derivatives, see: Beraldo & Gambino (2004 ). For the synthesis, see: Joseph et al. (2006 ). For related structures of hydrazinecarbothioamides, see: Philip et al. (2006 ); Arumugam et al. (2011 ). For related structures, see: Seena et al. (2008 ); Usman et al. (2002 ); Huheey et al. (1993 ); Joseph et al. (2004 ).

Experimental

Crystal data

C₁₅H₁₆N₄S
M_r = 284.39
Monoclinic, P 2₁ /c
a = 10.011 (2) Å
b = 8.888 (2) Å
c = 16.256 (4) Å
β = 94.528 (3)°
V = 1441.9 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.22 mm⁻¹
T = 153 K
0.32 × 0.28 × 0.22 mm

Data collection

Bruker P4 diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2004 ) T_min = 0.932, T_max = 0.953
14231 measured reflections
2828 independent reflections
2405 reflections with I > 2σ(I)
R_int = 0.031

Refinement

R[F² > 2σ(F²)] = 0.039
wR(F²) = 0.110
S = 1.06
2828 reflections
188 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the N1/C8–C12 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3′⋯N1	0.837 (17)	1.869 (17)	2.602 (2)	145.4 (15)
C5—H5⋯Cgⁱ	0.93	2.66	3.536 (2)	157
Symmetry code: (i) -x+2, -y+1, -z+1.

Data collection: SMART (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008) and ORTEP-3 (Farrugia, 1997 ); software used to prepare material for publication: SHELXL97 and publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536811045739/fj2463sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811045739/fj2463Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536811045739/fj2463Isup3.cml

checkCIF report

Comment top

A large number of studies have been devoted to the search for derivatives of hydrazinecarbothioamide, which have been used as drugs and have the ability to form complexes. The biological activity of these compounds depends on the parent aldehyde or ketone (Beraldo & Gambino, 2004). Derivatives of hydrazinecarbothioamide constitute an important group of multidentate ligands with potential binding sites available for a wide variety of metal ions. These thiourea derivatives find substantial applications in different facets of contemporary scientific research.

The title compound (Z)-2-N,N-dimethyl-2-[phenyl(pyridin-2-yl)methylidene]hydrazinecarbothioamide is found to exist in Z configuration. A perspective view of the molecular structure of the title compound, along with the atom-labeling scheme, is given in Fig. 1. The S1= C13–N3–N2 torsion-angle [14.4 (2)°] indicates that thionyl atom S1 is positioned cis to azomethane nitrogen atom N2. The hydrazinecarbothioamide moiety adopts an extended conjugation, with electron delocalization throughout the N4/C13/S1/N3/N2 group. The fact that the compound exists in the thione form is confirmed by the N3—N2, N4—C13 and C13=S1 bond distances. The C13=S1 bond distance is close to that expected for a C=S double bond of 1.60 Å (Huheey et al., 1993). The N3—N2 bond distance is very close to the reported similar substituted hydrazinecarbothioamide (Joseph et al., 2004). The resonance form involving pyridine ring would account for the shortening of the N—N distance through extensive electron delocalization.

The hydrazinecarbothioamide moiety, comprising atoms N3, C13, S1 and N4, is almost planar with the maximum deviation of 0.013 (2) Å for atom N4. The pyridyl ring and phenyl ring are not in the same plane and the pyridyl ring is twisted significantly from the hydrazinecarbothioamide plane, with a torsionl angle of -176.3 (2)°.

Two types of intramolecular (classical and non-classical) hydrogen bond interactions are found in this molecule. A classical hydrogen bonding interaction between the hydrogen attached to the N3 nitrogen and the N1 nitrogen with the D···A distance of 2.602 (2) Å and the non-classical hydrogen bonding interaction between one of the hydrogen atom attached to the C14 atom and the S1 atom of the molecule with a D···A distance of 3.030 (2) Å as described in Table 1.

Fig. 2 shows the packing diagram of the title compound. Packing of these molecules does not include any classical intermolecular hydrogen bonding interactions in its molecular array. However, it may be directed by the C—H···π interaction between the pyridine ring and the hydrogen attached at C5 carbon atom of the phenyl ring of the another molecule. There are four very weak π–π interactions present in this molecular array with the distances of 5.5874 (17), 4.8708 (15), 5.5455 (17) and 4.9165 (15) Å between the centroids of the corresponding rings involving interactions.

Related literature top

For abackground to hydrazinecarbothioamide and its derivatives, see: Beraldo & Gambino (2004). For the synthesis, see: Joseph et al. (2006). For related structures of hydrazinecarbothioamides, see: Philip et al. (2006); Arumugam et al. (2011). For related structures, see: Seena et al. (2008); Usman et al. (2002); Huheey et al. (1993); Joseph et al. (2004).

Experimental top

The title compound was prepared by adapting a reported procedure (Joseph et al., 2006) by refluxing a mixture of methanolic solutions of 2-benzoylpyridine (11 mmol, 2.032 g) and N,N-dimethylhydrazinecarbothioamide (11 mmol, 1.320 g) for five hours after adding 5 drops of acetic acid. Yellow crystals were collected, washed with few drops of methanol and dried over P₄O₁₀ in vacuo. Single crystals of the title compound suitable for X-ray analysis were obtained by slow evaporation from its methanolic solution.

Structure description top

For abackground to hydrazinecarbothioamide and its derivatives, see: Beraldo & Gambino (2004). For the synthesis, see: Joseph et al. (2006). For related structures of hydrazinecarbothioamides, see: Philip et al. (2006); Arumugam et al. (2011). For related structures, see: Seena et al. (2008); Usman et al. (2002); Huheey et al. (1993); Joseph et al. (2004).

Computing details top

Data collection: SMART (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008) and ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and publCIF (Westrip, 2010).

Figures top

	Fig. 1. The molecular structure of the title compound with displacement ellipsoids are drawn at 50% probability level.
	Fig. 2. Packing diagram of the title compound, the unit cell is viewed down the a axis.

(Z)-N,N-Dimethyl-2-[phenyl(pyridin-2- yl)methylidene]hydrazinecarbothioamide top

Crystal data top

C₁₅H₁₆N₄S	F(000) = 600.0
M_r = 284.39	D_x = 1.310 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 8120 reflections
a = 10.011 (2) Å	θ = 2.0–26.0°
b = 8.888 (2) Å	µ = 0.22 mm⁻¹
c = 16.256 (4) Å	T = 153 K
β = 94.528 (3)°	Block, yellow
V = 1441.9 (6) Å³	0.32 × 0.28 × 0.22 mm
Z = 4

Data collection top

Bruker P4 diffractometer	2828 independent reflections
Radiation source: fine-focus sealed tube	2405 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.031
Detector resolution: 8.33 pixels mm^-1	θ_max = 26.0°, θ_min = 2.0°
ω scans	h = −12→12
Absorption correction: multi-scan (SADABS; Bruker, 2004)	k = −10→10
T_min = 0.932, T_max = 0.953	l = −20→20
14231 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.039	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.110	w = 1/[σ²(F_o²) + (0.0606P)² + 0.2366P] where P = (F_o² + 2F_c²)/3
S = 1.06	(Δ/σ)_max = 0.014
2828 reflections	Δρ_max = 0.19 e Å⁻³
188 parameters	Δρ_min = −0.20 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0104 (16)

Crystal data top

C₁₅H₁₆N₄S	V = 1441.9 (6) Å³
M_r = 284.39	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 10.011 (2) Å	µ = 0.22 mm⁻¹
b = 8.888 (2) Å	T = 153 K
c = 16.256 (4) Å	0.32 × 0.28 × 0.22 mm
β = 94.528 (3)°

Data collection top

Bruker P4 diffractometer	2828 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2004)	2405 reflections with I > 2σ(I)
T_min = 0.932, T_max = 0.953	R_int = 0.031
14231 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	0 restraints
wR(F²) = 0.110	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	Δρ_max = 0.19 e Å⁻³
2828 reflections	Δρ_min = −0.20 e Å⁻³
188 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
S1	0.75460 (4)	0.15132 (5)	0.31975 (3)	0.05808 (18)
N1	0.98755 (14)	0.68420 (14)	0.33757 (8)	0.0466 (3)
N2	0.99018 (12)	0.35758 (13)	0.36663 (7)	0.0413 (3)
N3	0.87523 (12)	0.42001 (16)	0.33015 (8)	0.0459 (3)
N4	0.68025 (13)	0.41370 (17)	0.25113 (9)	0.0552 (4)
C1	1.33165 (15)	0.42244 (19)	0.39734 (10)	0.0496 (4)
H1	1.3333	0.4983	0.3580	0.059*
C2	1.44999 (16)	0.3531 (2)	0.42682 (12)	0.0584 (5)
H2	1.5307	0.3820	0.4069	0.070*
C3	1.44848 (18)	0.2420 (2)	0.48527 (12)	0.0604 (5)
H3	1.5280	0.1956	0.5048	0.072*
C4	1.32983 (18)	0.1993 (2)	0.51494 (11)	0.0586 (5)
H4	1.3291	0.1248	0.5551	0.070*
C5	1.21090 (16)	0.26692 (18)	0.48536 (10)	0.0474 (4)
H5	1.1305	0.2368	0.5053	0.057*
C6	1.21111 (14)	0.37895 (16)	0.42634 (9)	0.0386 (3)
C7	1.08395 (14)	0.45037 (16)	0.39224 (8)	0.0383 (3)
C8	1.07742 (14)	0.61797 (16)	0.39196 (9)	0.0404 (3)
C9	1.15590 (16)	0.70179 (18)	0.44910 (10)	0.0499 (4)
H9	1.2173	0.6546	0.4865	0.060*
C10	1.14187 (19)	0.85641 (19)	0.44978 (13)	0.0600 (5)
H10	1.1928	0.9143	0.4882	0.072*
C11	1.05114 (18)	0.92430 (19)	0.39262 (12)	0.0574 (4)
H11	1.0408	1.0283	0.3912	0.069*
C12	0.97729 (18)	0.83393 (18)	0.33834 (11)	0.0527 (4)
H12	0.9165	0.8793	0.2998	0.063*
C13	0.77074 (15)	0.33429 (18)	0.29902 (9)	0.0442 (4)
C14	0.56134 (19)	0.3425 (3)	0.21167 (14)	0.0755 (6)
H14A	0.5778	0.3140	0.1564	0.113*
H14B	0.4877	0.4119	0.2101	0.113*
H14C	0.5400	0.2547	0.2424	0.113*
C15	0.6980 (2)	0.5728 (2)	0.23277 (14)	0.0770 (6)
H15A	0.6945	0.6306	0.2824	0.115*
H15B	0.6279	0.6051	0.1930	0.115*
H15C	0.7833	0.5874	0.2108	0.115*
H3'	0.8833 (15)	0.511 (2)	0.3188 (9)	0.043 (4)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0506 (3)	0.0477 (3)	0.0740 (3)	−0.00580 (18)	−0.0075 (2)	−0.00052 (19)
N1	0.0516 (8)	0.0409 (7)	0.0469 (7)	0.0035 (6)	0.0016 (6)	0.0030 (5)
N2	0.0353 (6)	0.0410 (7)	0.0462 (7)	0.0030 (5)	−0.0045 (5)	0.0000 (5)
N3	0.0394 (7)	0.0388 (7)	0.0574 (8)	0.0035 (5)	−0.0087 (6)	0.0003 (6)
N4	0.0427 (7)	0.0588 (9)	0.0613 (8)	0.0069 (6)	−0.0143 (6)	−0.0006 (7)
C1	0.0441 (9)	0.0505 (9)	0.0542 (9)	0.0001 (7)	0.0042 (7)	0.0044 (7)
C2	0.0347 (8)	0.0697 (12)	0.0705 (11)	0.0005 (8)	0.0022 (8)	−0.0032 (9)
C3	0.0425 (9)	0.0639 (11)	0.0711 (11)	0.0098 (8)	−0.0182 (8)	−0.0052 (9)
C4	0.0562 (10)	0.0552 (10)	0.0611 (10)	0.0010 (8)	−0.0157 (8)	0.0113 (8)
C5	0.0418 (8)	0.0478 (9)	0.0513 (9)	−0.0055 (7)	−0.0045 (7)	0.0039 (7)
C6	0.0363 (7)	0.0361 (7)	0.0421 (8)	0.0002 (6)	−0.0042 (6)	−0.0050 (6)
C7	0.0372 (7)	0.0394 (7)	0.0380 (7)	0.0016 (6)	0.0014 (6)	−0.0007 (6)
C8	0.0373 (7)	0.0400 (8)	0.0442 (8)	0.0019 (6)	0.0058 (6)	0.0004 (6)
C9	0.0448 (9)	0.0463 (9)	0.0577 (9)	−0.0007 (7)	−0.0016 (7)	−0.0048 (7)
C10	0.0582 (11)	0.0457 (10)	0.0756 (12)	−0.0065 (8)	0.0024 (9)	−0.0123 (8)
C11	0.0634 (11)	0.0360 (8)	0.0745 (11)	−0.0007 (8)	0.0162 (9)	−0.0006 (8)
C12	0.0595 (10)	0.0438 (9)	0.0553 (9)	0.0074 (7)	0.0069 (8)	0.0092 (7)
C13	0.0373 (8)	0.0499 (9)	0.0444 (8)	0.0043 (6)	−0.0021 (6)	−0.0052 (6)
C14	0.0502 (11)	0.0935 (16)	0.0781 (13)	0.0042 (10)	−0.0250 (10)	−0.0092 (11)
C15	0.0699 (13)	0.0660 (13)	0.0902 (15)	0.0183 (10)	−0.0245 (11)	0.0121 (11)

Geometric parameters (Å, º) top

S1—C13	1.6712 (17)	C5—C6	1.383 (2)
N1—C12	1.335 (2)	C5—H5	0.9300
N1—C8	1.3461 (19)	C6—C7	1.4898 (19)
N2—C7	1.2934 (18)	C7—C8	1.491 (2)
N2—N3	1.3697 (17)	C8—C9	1.386 (2)
N3—C13	1.3591 (19)	C9—C10	1.381 (2)
N3—H3'	0.837 (17)	C9—H9	0.9300
N4—C13	1.3466 (19)	C10—C11	1.385 (3)
N4—C14	1.452 (2)	C10—H10	0.9300
N4—C15	1.459 (3)	C11—C12	1.366 (2)
C1—C6	1.385 (2)	C11—H11	0.9300
C1—C2	1.387 (2)	C12—H12	0.9300
C1—H1	0.9300	C14—H14A	0.9600
C2—C3	1.371 (3)	C14—H14B	0.9600
C2—H2	0.9300	C14—H14C	0.9600
C3—C4	1.370 (3)	C15—H15A	0.9600
C3—H3	0.9300	C15—H15B	0.9600
C4—C5	1.385 (2)	C15—H15C	0.9600
C4—H4	0.9300

C12—N1—C8	118.54 (14)	N1—C8—C7	117.75 (13)
C7—N2—N3	116.40 (12)	C9—C8—C7	120.85 (13)
C13—N3—N2	121.99 (13)	C10—C9—C8	119.18 (16)
C13—N3—H3'	123.1 (11)	C10—C9—H9	120.4
N2—N3—H3'	113.3 (11)	C8—C9—H9	120.4
C13—N4—C14	121.18 (15)	C9—C10—C11	119.31 (16)
C13—N4—C15	122.61 (14)	C9—C10—H10	120.3
C14—N4—C15	116.16 (14)	C11—C10—H10	120.3
C6—C1—C2	120.13 (16)	C12—C11—C10	118.02 (15)
C6—C1—H1	119.9	C12—C11—H11	121.0
C2—C1—H1	119.9	C10—C11—H11	121.0
C3—C2—C1	120.23 (16)	N1—C12—C11	123.63 (16)
C3—C2—H2	119.9	N1—C12—H12	118.2
C1—C2—H2	119.9	C11—C12—H12	118.2
C4—C3—C2	120.04 (16)	N4—C13—N3	112.61 (14)
C4—C3—H3	120.0	N4—C13—S1	123.72 (12)
C2—C3—H3	120.0	N3—C13—S1	123.65 (11)
C3—C4—C5	120.19 (16)	N4—C14—H14A	109.5
C3—C4—H4	119.9	N4—C14—H14B	109.5
C5—C4—H4	119.9	H14A—C14—H14B	109.5
C6—C5—C4	120.31 (15)	N4—C14—H14C	109.5
C6—C5—H5	119.8	H14A—C14—H14C	109.5
C4—C5—H5	119.8	H14B—C14—H14C	109.5
C5—C6—C1	119.09 (14)	N4—C15—H15A	109.5
C5—C6—C7	121.12 (13)	N4—C15—H15B	109.5
C1—C6—C7	119.77 (13)	H15A—C15—H15B	109.5
N2—C7—C6	115.17 (12)	N4—C15—H15C	109.5
N2—C7—C8	127.26 (13)	H15A—C15—H15C	109.5
C6—C7—C8	117.56 (12)	H15B—C15—H15C	109.5
N1—C8—C9	121.30 (14)

C7—N2—N3—C13	178.44 (14)	N2—C7—C8—N1	−23.7 (2)
C6—C1—C2—C3	−0.5 (3)	C6—C7—C8—N1	157.05 (13)
C1—C2—C3—C4	−0.2 (3)	N2—C7—C8—C9	152.63 (15)
C2—C3—C4—C5	0.8 (3)	C6—C7—C8—C9	−26.6 (2)
C3—C4—C5—C6	−0.7 (3)	N1—C8—C9—C10	−0.4 (2)
C4—C5—C6—C1	0.0 (2)	C7—C8—C9—C10	−176.54 (16)
C4—C5—C6—C7	178.48 (14)	C8—C9—C10—C11	−0.9 (3)
C2—C1—C6—C5	0.6 (2)	C9—C10—C11—C12	1.0 (3)
C2—C1—C6—C7	−177.91 (14)	C8—N1—C12—C11	−1.5 (3)
N3—N2—C7—C6	−175.96 (12)	C10—C11—C12—N1	0.2 (3)
N3—N2—C7—C8	4.8 (2)	C14—N4—C13—N3	179.72 (16)
C5—C6—C7—N2	−50.15 (19)	C15—N4—C13—N3	2.5 (2)
C1—C6—C7—N2	128.32 (15)	C14—N4—C13—S1	−1.7 (2)
C5—C6—C7—C8	129.21 (15)	C15—N4—C13—S1	−178.84 (15)
C1—C6—C7—C8	−52.32 (19)	N2—N3—C13—N4	−166.98 (14)
C12—N1—C8—C9	1.5 (2)	N2—N3—C13—S1	14.4 (2)
C12—N1—C8—C7	177.81 (14)

Hydrogen-bond geometry (Å, º) top

Cg is the centroid of the N1/C8–C12 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3′···N1	0.837 (17)	1.869 (17)	2.602 (2)	145.4 (15)
C14—H14C···S1	0.96	2.57	3.030 (2)	109
C5—H5···Cgⁱ	0.93	2.66	3.536 (2)	157

Symmetry code: (i) −x+2, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₅H₁₆N₄S
M_r	284.39
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	153
a, b, c (Å)	10.011 (2), 8.888 (2), 16.256 (4)
β (°)	94.528 (3)
V (Å³)	1441.9 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.22
Crystal size (mm)	0.32 × 0.28 × 0.22

Data collection
Diffractometer	Bruker P4
Absorption correction	Multi-scan (SADABS; Bruker, 2004)
T_min, T_max	0.932, 0.953
No. of measured, independent and observed [I > 2σ(I)] reflections	14231, 2828, 2405
R_int	0.031
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.110, 1.06
No. of reflections	2828
No. of parameters	188
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.19, −0.20

Computer programs: SMART (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008) and ORTEP-3 (Farrugia, 1997), SHELXL97 (Sheldrick, 2008) and publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

Cg is the centroid of the N1/C8–C12 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3'···N1	0.837 (17)	1.869 (17)	2.602 (2)	145.4 (15)
C14—H14C···S1	0.96	2.57	3.030 (2)	109.4
C5—H5···Cgⁱ	0.93	2.66	3.536 (2)	157

Symmetry code: (i) −x+2, −y+1, −z+1.

Acknowledgements

KJ thanks the UGC, New Delhi, for the award of a Teacher Fellowship. The authors also thank the STIC, CUSAT, Kochi-22, for providing the single-crystal XRD data.

References

Arumugam, S. R., Dasary, S. S. R., Venkatraman, R., Yu, H. & Fronczek, F. R. (2011). Acta Cryst. E67, m1409–m1410. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
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Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

(Z)-N,N-Di­methyl-2-[phen­yl(pyridin-2-yl)methyl­­idene]hydrazinecarbo­thio­amide

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

(Z)-N,N-Dimethyl-2-[phenyl(pyridin-2-yl)methylidene]hydrazinecarbothioamide