2-Methyl-N-[(3-methyl-2-pyrid­yl)carbamothio­yl]benzamide

Yamin, B.M.; Yousuf, S.; Yusof, M.S.M.; Jusoh, R.H.

doi:10.1107/S1600536808009513

organic compounds

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ISSN: 2056-9890

Volume 64| Part 5| May 2008| Page o833

doi:10.1107/S1600536808009513

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2-Methyl-N-[(3-methyl-2-pyridyl)carbamothioyl]benzamide

B. M. Yamin,^a S. Yousuf,^b ^* M. S. M. Yusof ^c and R. H. Jusoh ^c

^aSchool of Chemical Sciences and Food Technology, Universiti Kebangsaan Malaysia, UKM 43500 Bangi Selangor, Malaysia, ^bHEJ Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, Karachi 75270, Pakistan, and ^cDepartment of Chemistry, Universiti Malaysia Terengganu, Manngabang Telipot, Terengganu, Malaysia
^*Correspondence e-mail: sammer_yousuf@yahoo.com

(Received 25 March 2008; accepted 7 April 2008; online 10 April 2008)

In the title compound, C₁₅H₁₅N₃OS, the thiourea group is stabilized by an intramolecular hydrogen bond between the carbonyl O atom and the thioamide group. A C—H⋯N intramolecular hydrogen bond is also present. Molecules are linked by intermolecular N—H⋯O and C—H⋯S hydrogen bonds.

Related literature

For the crystal structure of N-(3-iodophenyl)-N′-(2-methylbenzoyl)thiourea, see: Yusof et al. (2007 ). For bond-length data, see: Allen et al. (1987 ).

Experimental

Crystal data

C₁₅H₁₅N₃OS
M_r = 285.36
Monoclinic, P 2₁ /n
a = 7.955 (3) Å
b = 7.811 (3) Å
c = 23.414 (8) Å
β = 90.827 (6)°
V = 1454.6 (9) Å³
Z = 4
Mo Kα radiation
μ = 0.22 mm⁻¹
T = 298 (2) K
0.49 × 0.46 × 0.17 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000 ) T_min = 0.899, T_max = 0.963
7524 measured reflections
2710 independent reflections
2099 reflections with I > 2σ(I)
R_int = 0.018

Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.112
S = 1.02
2710 reflections
191 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.13 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O1	0.86 (2)	2.04 (2)	2.697 (2)	132.2 (18)
C15—H15A⋯N2	0.96	2.56	2.961	105
N2—H2⋯O1ⁱ	0.86 (2)	2.30 (2)	3.021 (2)	142 (2)
C13—H13⋯S1ⁱⁱ	0.93	2.85	3.700	154
Symmetry codes: (i) -x+1, -y+1, -z; (ii) $[-x+{\script{3\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); 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); software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995 ) and PLATON (Spek, 2003 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808009513/sg2229sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808009513/sg2229Isup2.hkl

checkCIF report

Comment top

The title compound, (I), is analogous to N-(3-iodophenyl)-N'-(2-methylbenzoyl) thiourea (II), (Yusof et al., 2007) except that the iodophenyl group is replaced by the 3-methylpyridine group (Fig.1). The bond lengths and angles are in normal range (Allen et al., 1987). The central thiourea moiety, S1/N1/N2/C9, pyridine, N3/(C10—C14), and benzene,(C1—C6) rings are each planar with maximum deviation of 0.033 (2)Å for N2 atom from the least square plane. The central thiourea moiety makes dihedral angle with the pyridine and benzene rings of 64.58 (8) and 62.03 (8)° respectively. The dihedral angle between the pyridine and benzene rings (4.03 (10)°) is smaller compared to that in (II) of 31.88 (9)°. The molecule maintains the trans-cis geometry of the thiourea moiety which is stabilized by the intrahydrogen bond between the carbonyl oxygen atom O1 and the thioamide hydrogen atom, H15A. In the crystal structure, the molecules are linked by the N2—H2···O1 and C13—H13···S1 intermolecular hydrogen bonds (symmtery codes as in Table 2).

Related literature top

For the crystal structure of N-(3-iodophenyl)-N'-(2-methylbenzoyl) thiourea, see: Yusof et al. (2007). For bond-length data, see: Allen et al. (1987).

Experimental top

The mixture of 2-methylbenzoyl chloride (9.720 g, 0.025mole) with the equimolar amount of ammonium thiocyanate (1.903 g, 0.025 mol) and 2-amino-3-methyl pyridine,(2.703 g, 0.025 mol) in 40 ml dry acetone was refluxed with stirring for 4 h. The solution was filtered and left to evaporate at room temperature. The colourless crystals obtained after a few days, was found suitable for X-ray investigations. The yield was 85% and the melting point is 412.3–413.8 K.

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008), PARST (Nardelli, 1995) and PLATON (Spek, 2003).

Figures top

	Fig. 1. The molecular Structure of (1) with displacement ellipsoids drawn at 50% probability level.The dashed lines indicates the intramolecular hydrogen bonds.
	Fig. 2. A packing diagram of (1). Hydrogen bonds are shown by dashed lines.

2-Methyl-N-[(3-methyl-2-pyridyl)carbamothioyl]benzamide top

Crystal data top

C₁₅H₁₅N₃OS	F(000) = 600
M_r = 285.36	D_x = 1.303 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2292 reflections
a = 7.955 (3) Å	θ = 1.7–25.5°
b = 7.811 (3) Å	µ = 0.22 mm⁻¹
c = 23.414 (8) Å	T = 298 K
β = 90.827 (6)°	Block, colourless
V = 1454.6 (9) Å³	0.49 × 0.46 × 0.17 mm
Z = 4

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	2710 independent reflections
Radiation source: fine-focus sealed tube	2099 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.019
Detector resolution: 83.66 pixels mm^-1	θ_max = 25.5°, θ_min = 1.7°
ω scans	h = −9→9
Absorption correction: multi-scan (SADABS; Bruker, 2000)	k = −9→9
T_min = 0.899, T_max = 0.963	l = −16→28
7524 measured reflections

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.112	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ²(F_o²) + (0.0591P)² + 0.3029P] where P = (F_o² + 2F_c²)/3
2710 reflections	(Δ/σ)_max < 0.001
191 parameters	Δρ_max = 0.24 e Å⁻³
1 restraint	Δρ_min = −0.13 e Å⁻³

Crystal data top

C₁₅H₁₅N₃OS	V = 1454.6 (9) Å³
M_r = 285.36	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 7.955 (3) Å	µ = 0.22 mm⁻¹
b = 7.811 (3) Å	T = 298 K
c = 23.414 (8) Å	0.49 × 0.46 × 0.17 mm
β = 90.827 (6)°

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	2710 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2000)	2099 reflections with I > 2σ(I)
T_min = 0.899, T_max = 0.963	R_int = 0.019
7524 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	1 restraint
wR(F²) = 0.112	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	Δρ_max = 0.24 e Å⁻³
2710 reflections	Δρ_min = −0.13 e Å⁻³
191 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	0.34243 (7)	0.20705 (8)	0.17685 (2)	0.0662 (2)
O1	0.40058 (17)	0.34898 (19)	−0.00872 (5)	0.0599 (4)
N1	0.26335 (19)	0.2529 (2)	0.06915 (6)	0.0485 (4)
H1	0.1847 (19)	0.183 (2)	0.0784 (8)	0.056 (6)*
N2	0.49690 (18)	0.4025 (2)	0.10075 (6)	0.0460 (4)
H2	0.513 (2)	0.429 (3)	0.0656 (9)	0.057 (6)*
N3	0.77881 (19)	0.3995 (2)	0.12320 (7)	0.0579 (4)
C1	0.1548 (2)	0.1298 (2)	−0.07366 (8)	0.0497 (5)
C2	0.0123 (3)	0.0935 (3)	−0.10668 (9)	0.0641 (6)
H2A	0.0238	0.0305	−0.1401	0.077*
C3	−0.1439 (3)	0.1477 (3)	−0.09150 (10)	0.0707 (7)
H3	−0.2358	0.1239	−0.1152	0.085*
C4	−0.1669 (3)	0.2364 (3)	−0.04197 (11)	0.0675 (6)
H4	−0.2737	0.2720	−0.0316	0.081*
C5	−0.0286 (2)	0.2727 (3)	−0.00736 (9)	0.0537 (5)
H5	−0.0430	0.3303	0.0270	0.064*
C6	0.1310 (2)	0.2234 (2)	−0.02376 (7)	0.0434 (4)
C7	0.3230 (3)	0.0627 (3)	−0.09092 (10)	0.0759 (7)
H7A	0.3091	−0.0141	−0.1226	0.114*
H7B	0.3742	0.0028	−0.0594	0.114*
H7C	0.3936	0.1565	−0.1018	0.114*
C8	0.2781 (2)	0.2805 (2)	0.01149 (7)	0.0433 (4)
C9	0.3749 (2)	0.2940 (2)	0.11353 (7)	0.0457 (4)
C10	0.6291 (2)	0.4528 (2)	0.13916 (7)	0.0437 (4)
C11	0.6000 (3)	0.5570 (3)	0.18580 (8)	0.0554 (5)
C12	0.7424 (3)	0.5988 (3)	0.21814 (9)	0.0688 (6)
H12	0.7315	0.6667	0.2505	0.083*
C13	0.8968 (3)	0.5421 (3)	0.20313 (10)	0.0745 (7)
H13	0.9914	0.5683	0.2252	0.089*
C14	0.9096 (3)	0.4468 (3)	0.15529 (10)	0.0732 (7)
H14	1.0162	0.4123	0.1442	0.088*
C15	0.4302 (3)	0.6260 (4)	0.20004 (11)	0.0852 (8)
H15A	0.3581	0.6201	0.1669	0.128*
H15B	0.4408	0.7430	0.2121	0.128*
H15C	0.3829	0.5593	0.2303	0.128*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0669 (4)	0.0892 (4)	0.0423 (3)	−0.0180 (3)	−0.0071 (2)	0.0199 (3)
O1	0.0565 (8)	0.0822 (10)	0.0411 (7)	−0.0295 (7)	0.0001 (6)	0.0024 (7)
N1	0.0422 (9)	0.0642 (10)	0.0390 (8)	−0.0158 (7)	−0.0032 (6)	0.0087 (7)
N2	0.0425 (8)	0.0628 (10)	0.0325 (8)	−0.0091 (7)	−0.0020 (6)	0.0037 (7)
N3	0.0422 (9)	0.0730 (11)	0.0585 (10)	−0.0011 (8)	−0.0012 (7)	−0.0153 (8)
C1	0.0598 (12)	0.0452 (10)	0.0441 (10)	−0.0082 (9)	−0.0028 (8)	0.0020 (8)
C2	0.0840 (16)	0.0569 (13)	0.0508 (11)	−0.0154 (12)	−0.0169 (11)	−0.0021 (10)
C3	0.0697 (15)	0.0612 (13)	0.0801 (16)	−0.0157 (11)	−0.0364 (13)	0.0138 (12)
C4	0.0452 (12)	0.0651 (14)	0.0919 (17)	−0.0024 (10)	−0.0117 (11)	0.0112 (13)
C5	0.0485 (12)	0.0559 (12)	0.0567 (12)	−0.0043 (9)	−0.0023 (9)	0.0011 (9)
C6	0.0455 (10)	0.0432 (9)	0.0413 (9)	−0.0070 (8)	−0.0044 (7)	0.0061 (8)
C7	0.0810 (16)	0.0757 (16)	0.0713 (15)	0.0002 (13)	0.0119 (12)	−0.0179 (12)
C8	0.0434 (10)	0.0456 (10)	0.0408 (9)	−0.0068 (8)	−0.0005 (7)	0.0018 (8)
C9	0.0387 (10)	0.0565 (11)	0.0418 (10)	−0.0005 (8)	−0.0014 (7)	0.0026 (8)
C10	0.0435 (10)	0.0508 (10)	0.0367 (9)	−0.0025 (8)	−0.0028 (7)	0.0003 (8)
C11	0.0634 (12)	0.0592 (12)	0.0435 (10)	0.0039 (10)	0.0008 (9)	−0.0035 (9)
C12	0.0903 (17)	0.0698 (15)	0.0459 (11)	−0.0074 (13)	−0.0106 (11)	−0.0148 (10)
C13	0.0637 (15)	0.0915 (18)	0.0675 (14)	−0.0146 (13)	−0.0233 (11)	−0.0064 (13)
C14	0.0435 (12)	0.0973 (18)	0.0785 (15)	−0.0010 (11)	−0.0096 (10)	−0.0162 (13)
C15	0.0838 (17)	0.0948 (18)	0.0774 (16)	0.0215 (14)	0.0110 (13)	−0.0214 (14)

Geometric parameters (Å, º) top

S1—C9	1.6545 (18)	C4—H4	0.9300
O1—C8	1.214 (2)	C5—C6	1.386 (3)
N1—C8	1.374 (2)	C5—H5	0.9300
N1—C9	1.394 (2)	C6—C8	1.490 (2)
N1—H1	0.860 (9)	C7—H7A	0.9600
N2—C9	1.326 (2)	C7—H7B	0.9600
N2—C10	1.429 (2)	C7—H7C	0.9600
N2—H2	0.86 (2)	C10—C11	1.384 (3)
N3—C10	1.321 (2)	C11—C12	1.392 (3)
N3—C14	1.327 (3)	C11—C15	1.497 (3)
C1—C2	1.392 (3)	C12—C13	1.357 (3)
C1—C6	1.394 (3)	C12—H12	0.9300
C1—C7	1.498 (3)	C13—C14	1.350 (3)
C2—C3	1.364 (3)	C13—H13	0.9300
C2—H2A	0.9300	C14—H14	0.9300
C3—C4	1.366 (3)	C15—H15A	0.9600
C3—H3	0.9300	C15—H15B	0.9600
C4—C5	1.386 (3)	C15—H15C	0.9600

C8—N1—C9	129.35 (15)	H7A—C7—H7C	109.5
C8—N1—H1	114.8 (13)	H7B—C7—H7C	109.5
C9—N1—H1	114.6 (13)	O1—C8—N1	122.17 (16)
C9—N2—C10	124.63 (15)	O1—C8—C6	122.97 (16)
C9—N2—H2	119.5 (13)	N1—C8—C6	114.85 (14)
C10—N2—H2	114.5 (13)	N2—C9—N1	116.05 (15)
C10—N3—C14	117.05 (18)	N2—C9—S1	126.06 (14)
C2—C1—C6	116.94 (19)	N1—C9—S1	117.88 (13)
C2—C1—C7	120.18 (19)	N3—C10—C11	124.77 (17)
C6—C1—C7	122.84 (18)	N3—C10—N2	113.16 (15)
C3—C2—C1	122.0 (2)	C11—C10—N2	121.92 (16)
C3—C2—H2A	119.0	C10—C11—C12	115.06 (19)
C1—C2—H2A	119.0	C10—C11—C15	123.32 (19)
C2—C3—C4	120.8 (2)	C12—C11—C15	121.6 (2)
C2—C3—H3	119.6	C13—C12—C11	121.0 (2)
C4—C3—H3	119.6	C13—C12—H12	119.5
C3—C4—C5	119.1 (2)	C11—C12—H12	119.5
C3—C4—H4	120.5	C14—C13—C12	118.4 (2)
C5—C4—H4	120.5	C14—C13—H13	120.8
C4—C5—C6	120.2 (2)	C12—C13—H13	120.8
C4—C5—H5	119.9	N3—C14—C13	123.7 (2)
C6—C5—H5	119.9	N3—C14—H14	118.1
C5—C6—C1	120.92 (17)	C13—C14—H14	118.1
C5—C6—C8	118.59 (16)	C11—C15—H15A	109.5
C1—C6—C8	120.42 (16)	C11—C15—H15B	109.5
C1—C7—H7A	109.5	H15A—C15—H15B	109.5
C1—C7—H7B	109.5	C11—C15—H15C	109.5
H7A—C7—H7B	109.5	H15A—C15—H15C	109.5
C1—C7—H7C	109.5	H15B—C15—H15C	109.5

C6—C1—C2—C3	0.5 (3)	C10—N2—C9—N1	−176.19 (16)
C7—C1—C2—C3	177.9 (2)	C10—N2—C9—S1	4.8 (3)
C1—C2—C3—C4	−1.8 (3)	C8—N1—C9—N2	14.3 (3)
C2—C3—C4—C5	0.7 (3)	C8—N1—C9—S1	−166.69 (16)
C3—C4—C5—C6	1.8 (3)	C14—N3—C10—C11	1.6 (3)
C4—C5—C6—C1	−3.1 (3)	C14—N3—C10—N2	177.29 (19)
C4—C5—C6—C8	173.72 (17)	C9—N2—C10—N3	113.7 (2)
C2—C1—C6—C5	2.0 (3)	C9—N2—C10—C11	−70.4 (3)
C7—C1—C6—C5	−175.40 (18)	N3—C10—C11—C12	−2.8 (3)
C2—C1—C6—C8	−174.81 (17)	N2—C10—C11—C12	−178.13 (18)
C7—C1—C6—C8	7.8 (3)	N3—C10—C11—C15	175.1 (2)
C9—N1—C8—O1	0.3 (3)	N2—C10—C11—C15	−0.2 (3)
C9—N1—C8—C6	−178.45 (18)	C10—C11—C12—C13	1.2 (3)
C5—C6—C8—O1	−129.5 (2)	C15—C11—C12—C13	−176.7 (2)
C1—C6—C8—O1	47.3 (3)	C11—C12—C13—C14	1.3 (4)
C5—C6—C8—N1	49.2 (2)	C10—N3—C14—C13	1.3 (4)
C1—C6—C8—N1	−133.98 (18)	C12—C13—C14—N3	−2.8 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O1	0.86 (2)	2.04 (2)	2.697 (2)	132.2 (18)
C15—H15A···N2	0.96	2.56	2.961	105
N2—H2···O1ⁱ	0.86 (2)	2.30 (2)	3.021 (2)	142 (2)
C13—H13···S1ⁱⁱ	0.93	2.85	3.700	154

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

Experimental details

Crystal data
Chemical formula	C₁₅H₁₅N₃OS
M_r	285.36
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	298
a, b, c (Å)	7.955 (3), 7.811 (3), 23.414 (8)
β (°)	90.827 (6)
V (Å³)	1454.6 (9)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.22
Crystal size (mm)	0.49 × 0.46 × 0.17

Data collection
Diffractometer	Bruker SMART APEX CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2000)
T_min, T_max	0.899, 0.963
No. of measured, independent and observed [I > 2σ(I)] reflections	7524, 2710, 2099
R_int	0.019
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.112, 1.02
No. of reflections	2710
No. of parameters	191
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.24, −0.13

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008), PARST (Nardelli, 1995) and PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O1	0.86 (2)	2.04 (2)	2.697 (2)	132.2 (18)
C15—H15A···N2	0.96	2.56	2.961	105
N2—H2···O1ⁱ	0.86 (2)	2.30 (2)	3.021 (2)	142 (2)
C13—H13···S1ⁱⁱ	0.93	2.85	3.700	154

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

Acknowledgements

The authors thank the Ministry of Higher Education of Malaysia for Fundamental Research Grants UKM-ST-01-FRGS-0003-2006 and UMT-FRGS-59001, and Universiti Kebangsaan Malaysia and HEJ Research Institute of Chemistry, University of Karachi, for research facilities.

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