4-Methyl-N-[2-(pyridin-2-yl)ethyl­carbamo­thio­yl]benzamide

Adam, F.; Ameram, N.; Eltayeb, N.E.

doi:10.1107/S1600536814016377

organic compounds

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ISSN: 2056-9890

Volume 70| Part 8| August 2014| Page o885

doi:10.1107/S1600536814016377

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4-Methyl-N-[2-(pyridin-2-yl)ethylcarbamothioyl]benzamide

Farook Adam,^a ^* Nadiah Ameram ^a and Naser Eltaher Eltayeb ^b ‡

^aSchool of Chemical Sciences, 11800, USM Pulau Pinang, Malaysia, and ^bCollege of Sciences and Arts, Rabigh, King Abdulaziz University, Saudi Arabia
^*Correspondence e-mail: farook@usm.my

Edited by G. Smith, Queensland University of Technology, Australia (Received 15 June 2014; accepted 15 July 2014; online 31 July 2014)

In the title compound, C₁₆H₁₇N₃OS, the dihedral angle between the planes of the benzene and pyridine rings is 71.33 (15)°. An intramolecular N—H⋯O hydrogen bond is present. In the crystal, weak aromatic C—H⋯O hydrogen bonds link the molecules into chains extending along a.

Keywords: crystal structure; hydrogen bonding; thiourea compounds; thiocarbonyl groups; benzamide.

CCDC reference: 1014035

Related literature

For related structures, see: Saeed & Flörke (2007 ); Yusof et al. (2008 , 2011 ); Shoukat et al. (2007 ); Hassan et al. (2008a ,b ,c ). For standard bond lengths, see: Allen et al. (1987 ). For graph-set analysis, see Bernstein et al. (1995 ).

Experimental

Crystal data

C₁₆H₁₇N₃OS
M_r = 299.39
Monoclinic, P 2₁ /c
a = 16.0467 (12) Å
b = 4.8824 (4) Å
c = 23.0403 (18) Å
β = 124.997 (5)°
V = 1478.7 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.22 mm⁻¹
T = 100 K
0.47 × 0.20 × 0.14 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.903, T_max = 0.980
12777 measured reflections
3409 independent reflections
2221 reflections with I > 2σ(I)
R_int = 0.082

Refinement

R[F² > 2σ(F²)] = 0.068
wR(F²) = 0.182
S = 1.04
3409 reflections
199 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.66 e Å⁻³
Δρ_min = −0.44 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H1N2⋯O2	0.87 (4)	1.90 (3)	2.645 (3)	143 (3)
C14—H14A⋯O2ⁱ	0.95	2.51	3.421 (4)	161
Symmetry code: (i) $[-x+2, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ).

Supporting information

CCDC reference: 1014035

Crystal structure: contains datablock I. DOI: 10.1107/S1600536814016377/zs2306sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814016377/zs2306Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536814016377/zs2306Isup3.cml

checkCIF report

Comment top

In the title compound, C₁₆H₁₇N₃SO (Fig. 1), the bond lengths and angles are generally normal compared to those in N-alkyl-N-benzoylthiourea compounds (Allen et al., 1987). The bond lengths of the carbonyl and thiocarbonyl groups [C7—O2 = 1.229 (5) Å and C8—S1 = 1.677 (4) Å, respectively] have typical C═O and C═S double-bond character (Yusof et al. 2011). However, the thiocarbonyl is longer compared to the typical C═S bond which is 1.660 (2) Å. The C—N bond lengths for the title compound [C7—N1 = 1.375 (4) Å, C8—N1 = 1.397 (4) Å, C9—N2 = 1.460 (4) Å, C11—N3 = 1.335 (4), C15—N3 = 1.351 (4) Å] are all shorter than the average C—N single bond length [1.472 (5) Å], thus showing varying degrees of single bond character (Yusof et al. 2008). These bond features in the structure are presumed as a result of the intramolecular H-bonding interactions "locking" the molecule into a planar six-membered ring structure and are consistent with the expected delocalization in the title compound, confimed by the C9—N2—C8 and C8—N1—C7 bond angles [125.0 (3) and 128.8 (3)°, respectively], showing sp² hybridization on the N2 and N1 atoms. The molecule maintains its cis–trans configuration with respect to the position of the methyl benzene and ethyl pyridine groups relative to the thiocarbonyl sulfur atom across the N1—C7 and N2—C8 bonds, respectively (Hassan et al. (2008b,2008c)). The conformation of the molecule with respect to the thiocarbonyl and carbonyl moieties is twisted, as refleced by the torsion angles [C8–N1–C7–O2, C7–N1–C8–N2 and C7—N1—C8—S1: 2.1 (5), -4.4 (4) and 175.9 (2)°, respectively. The angle between the benzene and pyridine rings is 71.33 (15)°. The N2 H-atom forms bifurcated intramolecular interactions with both a carbonyl O-atom and the pyridine N-atom (Table 1): a hydrogen bond with O2 (N2—H···O2) and an interaction with N3 (N2—H···N3), giving cyclic motifs [graph sets S6 (Bernstein et al., 1995)]. Present also are weak intramolecular C1—H···O2 and C9—H···S1 interactions [graph set S(5)]. In the crystal, molecules are connected through weak intermolecular C14—H···O2 hydrogen-bonding interactions, giving one-dimensional chain structures extending along x (Fig. 2). The N1—H1N1 group has no acceptor in the crystal.

Experimental top

Synthesis and crystallization top

Freshly prepared substituted p-benzoyl chloride (13 mmol) was added dropwise to a stirred acetone solution (30 ml) of ammonium thiocyanate (13 mmol). The mixture was stirred for 10 min. A solution of 2-(2-aminethylpyridine) in acetone was added and the reaction mixture was refluxed for 3 h., after which the solution was poured into a beaker containing some ice cubes. The resulting precipitate was collected by filtration, washed several times with a cold ethanol/water mixture and purified by recrystallization from ethanol (Hassan et al., 2008a). Yield 65%; white transparent crystals, m.p. 126.3 °C. Anal Calc. for C16 H17 N3 O S: C, 64.9; H, 5.6; N, 15.9; S, 8.2%. Found: C, 64.8; H, 5.7; N, 14.8; S, 8.7%.

Refinement top

The H-atoms on the N atoms were located in a difference-Fourier and were fully refined. All other H-atoms were positioned geometrically and refined using a riding model with C—H = 0.95–0.99 Å and U_iso(H) = 1.2U_eq(aromatic C), 1.5U_eq(methyl C) and 1.2U_eq(methylene C).

Related literature top

For related structures, see: Saeed & Flörke (2007); Yusof et al. (2008); Shoukat et al. (2007). For standard bond lengths, see: Allen et al. (1987). For related literature, see: Hassan et al. (2008a,b,c); Saeed & Flörke (2007); Yusof et al. (2011). For graph-set analysis, see Bernstein et al. (1995).

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound, showing 50% probability displacement ellipsoids and the atom-numbering scheme. Intramolecular interactions are shown as dashed lines.
	Fig. 2. The crystal packing of the title compound viewed down the c axis. Hydrogen bonds are shown as dashed lines.

(I) top

Crystal data top

C₁₆H₁₇N₃OS	F(000) = 632
M_r = 299.39	D_x = 1.345 Mg m⁻³
Monoclinic, P2₁/c	Melting point: 399.3 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 16.0467 (12) Å	θ = 2.6–25.5°
b = 4.8824 (4) Å	µ = 0.22 mm⁻¹
c = 23.0403 (18) Å	T = 100 K
β = 124.997 (5)°	Block, colourless
V = 1478.7 (2) Å³	0.47 × 0.20 × 0.14 mm
Z = 4

Data collection top

Bruker APEXII CCD diffractometer	3409 independent reflections
Radiation source: fine-focus sealed tube	2221 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.082
ϕ and ω scans	θ_max = 27.6°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −17→20
T_min = 0.903, T_max = 0.980	k = −6→6
12777 measured reflections	l = −30→24

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)] = 0.068	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.182	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ²(F_o²) + (0.0899P)²] where P = (F_o² + 2F_c²)/3
3409 reflections	(Δ/σ)_max < 0.001
199 parameters	Δρ_max = 0.66 e Å⁻³
0 restraints	Δρ_min = −0.44 e Å⁻³

Crystal data top

C₁₆H₁₇N₃OS	V = 1478.7 (2) Å³
M_r = 299.39	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 16.0467 (12) Å	µ = 0.22 mm⁻¹
b = 4.8824 (4) Å	T = 100 K
c = 23.0403 (18) Å	0.47 × 0.20 × 0.14 mm
β = 124.997 (5)°

Data collection top

Bruker APEXII CCD diffractometer	3409 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	2221 reflections with I > 2σ(I)
T_min = 0.903, T_max = 0.980	R_int = 0.082
12777 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.068	0 restraints
wR(F²) = 0.182	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 0.66 e Å⁻³
3409 reflections	Δρ_min = −0.44 e Å⁻³
199 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	0.72652 (6)	0.04528 (17)	0.87044 (4)	0.0286 (3)
O2	0.78657 (14)	0.5226 (4)	0.72802 (11)	0.0272 (5)
N1	0.69712 (19)	0.3898 (5)	0.77218 (13)	0.0227 (6)
N2	0.84392 (17)	0.1337 (5)	0.82384 (13)	0.0211 (5)
N3	1.02858 (17)	0.3126 (5)	0.84401 (12)	0.0229 (6)
C1	0.6442 (2)	0.9043 (6)	0.63777 (15)	0.0236 (7)
H1A	0.7034	0.8759	0.6386	0.028*
C2	0.5737 (2)	1.0965 (6)	0.59246 (15)	0.0250 (7)
H2A	0.5853	1.1996	0.5627	0.030*
C3	0.4852 (2)	1.1422 (6)	0.58956 (15)	0.0227 (6)
C4	0.4718 (2)	0.9901 (6)	0.63468 (16)	0.0246 (7)
H4A	0.4128	1.0199	0.6341	0.030*
C5	0.5426 (2)	0.7954 (6)	0.68073 (15)	0.0245 (7)
H5A	0.5315	0.6933	0.7108	0.029*
C6	0.6301 (2)	0.7508 (6)	0.68249 (14)	0.0200 (6)
C7	0.7113 (2)	0.5479 (6)	0.72911 (14)	0.0203 (6)
C8	0.7611 (2)	0.1903 (6)	0.82127 (15)	0.0218 (6)
C9	0.9261 (2)	−0.0462 (6)	0.87572 (15)	0.0240 (7)
H9A	0.9508	−0.1556	0.8523	0.029*
H9B	0.9001	−0.1743	0.8952	0.029*
C10	1.0135 (2)	0.1207 (6)	0.93572 (15)	0.0242 (7)
H10A	0.9874	0.2330	0.9578	0.029*
H10B	1.0650	−0.0066	0.9723	0.029*
C11	1.0649 (2)	0.3085 (6)	0.91261 (15)	0.0224 (6)
C12	1.1454 (2)	0.4739 (6)	0.96253 (16)	0.0282 (7)
H12A	1.1707	0.4633	1.0112	0.034*
C13	1.1880 (2)	0.6550 (7)	0.93981 (18)	0.0315 (8)
H13A	1.2426	0.7710	0.9728	0.038*
C14	1.1503 (2)	0.6643 (6)	0.86918 (18)	0.0323 (8)
H14A	1.1775	0.7882	0.8523	0.039*
C15	1.0716 (2)	0.4885 (6)	0.82314 (17)	0.0269 (7)
H15A	1.0466	0.4919	0.7745	0.032*
C16	0.4073 (2)	1.3480 (6)	0.53901 (16)	0.0279 (7)
H16C	0.3579	1.3783	0.5505	0.042*
H16D	0.3721	1.2787	0.4904	0.042*
H16A	0.4412	1.5211	0.5431	0.042*
H1N2	0.852 (2)	0.242 (7)	0.7974 (17)	0.039 (10)*
H1N1	0.651 (3)	0.424 (9)	0.775 (2)	0.078 (15)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0251 (4)	0.0384 (5)	0.0310 (5)	0.0068 (3)	0.0211 (4)	0.0085 (3)
O2	0.0175 (11)	0.0343 (12)	0.0359 (12)	0.0052 (9)	0.0189 (10)	0.0070 (9)
N1	0.0166 (13)	0.0302 (14)	0.0268 (14)	0.0042 (10)	0.0157 (12)	0.0023 (10)
N2	0.0151 (12)	0.0249 (14)	0.0253 (14)	0.0030 (10)	0.0127 (11)	0.0040 (10)
N3	0.0185 (13)	0.0269 (14)	0.0266 (14)	0.0036 (10)	0.0149 (11)	0.0030 (10)
C1	0.0173 (14)	0.0322 (17)	0.0246 (16)	−0.0003 (12)	0.0140 (13)	0.0001 (12)
C2	0.0212 (15)	0.0317 (17)	0.0258 (16)	0.0013 (12)	0.0156 (13)	0.0055 (13)
C3	0.0184 (15)	0.0252 (16)	0.0234 (16)	0.0012 (12)	0.0114 (13)	−0.0001 (12)
C4	0.0180 (15)	0.0286 (16)	0.0311 (17)	0.0010 (12)	0.0163 (13)	0.0005 (13)
C5	0.0235 (16)	0.0284 (17)	0.0273 (16)	0.0017 (12)	0.0180 (14)	0.0038 (13)
C6	0.0154 (14)	0.0229 (15)	0.0214 (15)	−0.0028 (11)	0.0104 (12)	−0.0031 (11)
C7	0.0165 (14)	0.0234 (15)	0.0212 (15)	−0.0030 (11)	0.0109 (12)	−0.0029 (12)
C8	0.0173 (14)	0.0265 (16)	0.0222 (15)	0.0005 (12)	0.0116 (12)	0.0002 (12)
C9	0.0208 (15)	0.0247 (16)	0.0303 (17)	0.0046 (12)	0.0169 (14)	0.0056 (12)
C10	0.0180 (15)	0.0315 (17)	0.0238 (16)	0.0037 (12)	0.0124 (13)	0.0037 (12)
C11	0.0156 (15)	0.0248 (16)	0.0285 (16)	0.0051 (12)	0.0137 (13)	0.0030 (12)
C12	0.0216 (16)	0.0360 (18)	0.0268 (17)	−0.0014 (13)	0.0137 (14)	−0.0002 (13)
C13	0.0214 (16)	0.0293 (17)	0.044 (2)	−0.0020 (13)	0.0185 (15)	−0.0035 (14)
C14	0.0265 (17)	0.0298 (18)	0.052 (2)	0.0030 (14)	0.0292 (17)	0.0059 (15)
C15	0.0246 (16)	0.0330 (18)	0.0327 (17)	0.0063 (13)	0.0220 (14)	0.0052 (13)
C16	0.0229 (16)	0.0327 (18)	0.0286 (17)	0.0048 (13)	0.0150 (14)	0.0027 (13)

Geometric parameters (Å, º) top

S1—C8	1.678 (3)	C5—H5A	0.9500
O2—C7	1.228 (3)	C6—C7	1.493 (4)
N1—C7	1.376 (4)	C9—C10	1.523 (4)
N1—C8	1.397 (4)	C9—H9A	0.9900
N1—H1N1	0.80 (5)	C9—H9B	0.9900
N2—C8	1.325 (3)	C10—C11	1.519 (4)
N2—C9	1.460 (3)	C10—H10A	0.9900
N2—H1N2	0.87 (3)	C10—H10B	0.9900
N3—C11	1.335 (4)	C11—C12	1.392 (4)
N3—C15	1.351 (4)	C12—C13	1.391 (4)
C1—C2	1.376 (4)	C12—H12A	0.9500
C1—C6	1.393 (4)	C13—C14	1.374 (4)
C1—H1A	0.9500	C13—H13A	0.9500
C2—C3	1.402 (4)	C14—C15	1.386 (4)
C2—H2A	0.9500	C14—H14A	0.9500
C3—C4	1.390 (4)	C15—H15A	0.9500
C3—C16	1.502 (4)	C16—H16C	0.9800
C4—C5	1.391 (4)	C16—H16D	0.9800
C4—H4A	0.9500	C16—H16A	0.9800
C5—C6	1.399 (4)

C7—N1—C8	128.8 (2)	N2—C9—H9A	109.5
C7—N1—H1N1	119 (3)	C10—C9—H9A	109.5
C8—N1—H1N1	111 (3)	N2—C9—H9B	109.5
C8—N2—C9	125.0 (2)	C10—C9—H9B	109.5
C8—N2—H1N2	113 (2)	H9A—C9—H9B	108.1
C9—N2—H1N2	121 (2)	C11—C10—C9	114.1 (2)
C11—N3—C15	117.7 (3)	C11—C10—H10A	108.7
C2—C1—C6	121.1 (3)	C9—C10—H10A	108.7
C2—C1—H1A	119.4	C11—C10—H10B	108.7
C6—C1—H1A	119.4	C9—C10—H10B	108.7
C1—C2—C3	120.9 (3)	H10A—C10—H10B	107.6
C1—C2—H2A	119.5	N3—C11—C12	122.6 (3)
C3—C2—H2A	119.5	N3—C11—C10	117.9 (3)
C4—C3—C2	117.8 (3)	C12—C11—C10	119.5 (3)
C4—C3—C16	121.4 (3)	C13—C12—C11	118.7 (3)
C2—C3—C16	120.8 (3)	C13—C12—H12A	120.6
C3—C4—C5	121.8 (3)	C11—C12—H12A	120.6
C3—C4—H4A	119.1	C14—C13—C12	119.3 (3)
C5—C4—H4A	119.1	C14—C13—H13A	120.3
C4—C5—C6	119.7 (3)	C12—C13—H13A	120.3
C4—C5—H5A	120.2	C13—C14—C15	118.4 (3)
C6—C5—H5A	120.2	C13—C14—H14A	120.8
C1—C6—C5	118.7 (3)	C15—C14—H14A	120.8
C1—C6—C7	116.4 (2)	N3—C15—C14	123.3 (3)
C5—C6—C7	124.9 (2)	N3—C15—H15A	118.4
O2—C7—N1	122.0 (3)	C14—C15—H15A	118.4
O2—C7—C6	121.0 (3)	C3—C16—H16C	109.5
N1—C7—C6	117.0 (2)	C3—C16—H16D	109.5
N2—C8—N1	115.7 (2)	H16C—C16—H16D	109.5
N2—C8—S1	126.4 (2)	C3—C16—H16A	109.5
N1—C8—S1	117.8 (2)	H16C—C16—H16A	109.5
N2—C9—C10	110.5 (2)	H16D—C16—H16A	109.5

C6—C1—C2—C3	−0.5 (5)	C9—N2—C8—N1	173.5 (3)
C1—C2—C3—C4	1.0 (4)	C9—N2—C8—S1	−6.9 (4)
C1—C2—C3—C16	−178.7 (3)	C7—N1—C8—N2	−4.4 (4)
C2—C3—C4—C5	−0.9 (4)	C7—N1—C8—S1	175.9 (2)
C16—C3—C4—C5	178.8 (3)	C8—N2—C9—C10	−98.0 (3)
C3—C4—C5—C6	0.4 (4)	N2—C9—C10—C11	−63.9 (3)
C2—C1—C6—C5	−0.1 (4)	C15—N3—C11—C12	−1.0 (4)
C2—C1—C6—C7	179.8 (3)	C15—N3—C11—C10	177.2 (3)
C4—C5—C6—C1	0.1 (4)	C9—C10—C11—N3	1.1 (4)
C4—C5—C6—C7	−179.7 (3)	C9—C10—C11—C12	179.4 (3)
C8—N1—C7—O2	2.1 (5)	N3—C11—C12—C13	1.5 (4)
C8—N1—C7—C6	−178.7 (3)	C10—C11—C12—C13	−176.6 (3)
C1—C6—C7—O2	0.8 (4)	C11—C12—C13—C14	−0.5 (4)
C5—C6—C7—O2	−179.3 (3)	C12—C13—C14—C15	−0.9 (4)
C1—C6—C7—N1	−178.3 (3)	C11—N3—C15—C14	−0.5 (4)
C5—C6—C7—N1	1.5 (4)	C13—C14—C15—N3	1.5 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1N2···O2	0.87 (4)	1.90 (3)	2.645 (3)	143 (3)
N2—H1N2···N3	0.87 (4)	2.41 (4)	2.860 (4)	113 (3)
C1—H1A···O2	0.95	2.42	2.751 (4)	100
C9—H9B···S1	0.99	2.72	3.166 (4)	108
C14—H14A···O2ⁱ	0.95	2.51	3.421 (4)	161

Symmetry code: (i) −x+2, y+1/2, −z+3/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1N2···O2	0.87 (4)	1.90 (3)	2.645 (3)	143 (3)
C14—H14A···O2ⁱ	0.95	2.51	3.421 (4)	161

Symmetry code: (i) −x+2, y+1/2, −z+3/2.

Footnotes

‡Additional address: Department of Chemistry, International University of Africa, Sudan

Acknowledgements

The authors thank Universiti Sains Malaysia for a research grant (No. PKIMIA846017) which partially supported this work.

References

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