research communications\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 71| Part 3| March 2015| Pages 315-317
doi:10.1107/S2056989015003412

Crystal structure of 4-methyl-N-[(4-methyl­pyridin-2-yl)carbamo­thioyl]­benzamide

CROSSMARK_Color_square_no_text.svg
Farook Adam,a* Nadiah Amerama and Naser Eltaher Eltayebb‡

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

Edited by W. T. A. Harrison, University of Aberdeen, Scotland (Received 8 February 2015; accepted 18 February 2015; online 28 February 2015)

In the title compound, C15H15N3OS, the dihedral angle between the planes of the benzene and pyridine rings is 26.86 (9)°. Intra­molecular N—H⋯O and C—H⋯S hydrogen bonds both generate S(6) rings. The C=O and C=S bonds lie to opposite sides of the mol­ecule. In the crystal, inversion dimers linked by pairs of N—H⋯S hydrogen bonds generate R22(8) loops.

CCDC reference: 1050132

1. Chemical context

The role of benzoyl thio­urea derivatives in coordination chemistry has been extensively studied and quite satisfactorily elucidated. As benzoyl thio­ureas have suitable C=O and C=S functional groups, they can be considered as useful chelating agents due to their ability to encapsulate metal ions into their coordinating moiety. Thio­urea and its derivatives have found extensive applications in the fields of medicine, agriculture and analytical chemistry. Thio­ureas are also known to exhibit a wide range of biological activities including anti­cancer (Saeed et al., 2010a[Saeed, S., Rashid, N., Ali, M. & Hussain, R. (2010a). Eur. J. Chem. 1, 200-205.]), anti­fungal (Saeed et al., 2010b[Saeed, S., Rashid, N., Ali, M., Hussain, R. & Jones, P. G. (2010b). Eur. J. Chem. 1, 221-227.]) and as agrochemicals (Xu et al., 2003[Xu, X., Qian, X., Li, Z., Huang, Q. & Chen, G. (2003). J. Fluor. Chem. 121, 51-54.]). As part of our studies in this area, we now describe the synthesis and structure of the title compound, (I)[link].

[Scheme 1]

2. Structural commentary

The title compound (Fig. 1[link]) is a benzoyl thio­urea derivative and analogous to a compound recently reported by us (Adam et al., 2014[Adam, F., Ameram, N. & Eltayeb, N. E. (2014). Acta Cryst. E70, o885.]), except that the other substituent is changed to methyl­pyridine and the thio­urea moiety is still in a para position. The dihedral angle between the planes of the benzene and pyridine rings is 26.86 (9)°. The C=O bond length of 1.225 (2) Å is comparable to that observed in N-benzoyl-N′-phenyl­thio­urea (Hassan et al., 2008a[Hassan, I. N., Yamin, B. M. & Kassim, M. B. (2008a). Acta Cryst. E64, o1727.]). The C—N bond lengths are in the range 1.328 (2)–1.417 (2) Å, shorter than the normal single C—N bond length (1.469 Å), indicating partial double-bond character owing to the resonance effect at the carbonyl­thio­urea moiety.

[Figure 1]
Figure 1
The mol­ecular structure of the title compound, with 50% probability displacement ellipsoids. Hydrogen bonds are shown as dashed lines.

As in most benzoyl thio­urea derivatives, an intra­molecular N—H⋯O hydrogen bond leads to the formation of an S(6) ring, namely, C7/N1/C8/N2/H2/O1. An intra­molecular C—H⋯S inter­action (C9/N2/C8/S1/H10/C10) also generates an S(6) ring (Fig. 1[link], Table 1[link]).

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
N2—H1N2⋯O1 0.82 (2) 1.94 (2) 2.644 (2) 144 (2)
N1—H1N1⋯S1i 0.81 (2) 2.74 (2) 3.511 (2) 158 (2)
C10—H10A⋯S1 0.93 2.57 3.221 (2) 127
Symmetry code: (i) -x+1, -y+2, -z+1.

3. Supra­molecular features

In the crystal of (I)[link], inversion dimers linked by pairs of N—H⋯S hydrogen bonds (Table 1[link], Fig. 2[link]) generate [R_{2}^{2}](8) loops. As free rotation about the N1—C7 and N2—C8 single bonds is hindered, the C=O and C=S bonds are unlikely to align at the same side of the mol­ecule in order to form a chelate with a metal ion.

[Figure 2]
Figure 2
The crystal packing of the title compound viewed down the c axis. Hydrogen bonds are shown as dashed lines.

4. Synthesis and crystallization

The title compound was prepared according to a slight modification of the method described by Hassan et al. (2008b[Hassan, I. N., Yamin, B. M. & Kassim, M. B. (2008b). Acta Cryst. E64, o2083.]). 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-amino-4-picoline 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 an ethanol solution.

5. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2[link]. The H-atoms on the N atoms were located in a difference-Fourier map and were freely refined. All other H atoms were positioned geometrically and refined using a riding model with C—H = 0.93–0.96 Å and Uiso(H) = 1.2Ueq(aromatic C) or 1.5Ueq(methyl C).

Table 2
Experimental details

Crystal data
Chemical formula C15H15N3OS
Mr 285.36
Crystal system, space group Monoclinic, P21/c
Temperature (K) 294
a, b, c (Å) 11.5297 (12), 6.1860 (6), 20.657 (2)
β (°) 101.431 (2)
V (Å3) 1444.1 (3)
Z 4
Radiation type Mo Kα
μ (mm−1) 0.22
Crystal size (mm) 0.38 × 0.34 × 0.09
 
Data collection
Diffractometer Bruker APEXII CCD
Absorption correction Multi-scan (SADABS; Bruker, 2005[Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.])
Tmin, Tmax 0.920, 0.981
No. of measured, independent and observed [I > 2σ(I)] reflections 15813, 4233, 2790
Rint 0.028
(sin θ/λ)max (Å−1) 0.706
 
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.048, 0.164, 1.05
No. of reflections 4233
No. of parameters 191
H-atom treatment H atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3) 0.27, −0.19
Computer programs: APEX2 and SAINT (Bruker, 2005[Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]), SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]) and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Supporting information

CCDC reference: 1050132

Crystal structure: contains datablock I. DOI: 10.1107/S2056989015003412/hb7367sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S2056989015003412/hb7367Isup2.hkl

Supporting information file. DOI: 10.1107/S2056989015003412/hb7367Isup3.cml

checkCIF report


Chemical context top

The role of benzoyl thio­urea derivatives in coordination chemistry has been extensively studied and quite satisfactorily elucidated. As benzoyl thio­ureas have suitable C=O and C=S functional groups, they can be considered as useful chelating agents due to their ability to encapsulate metal ions into their coordinating moiety. Thio­urea and its derivatives have found extensive applications in the fields of medicine, agriculture and analytical chemistry. Thio­ureas are also known to exhibit a wide range of biological activities including anti­cancer (Saeed et al., 2010a), anti­fungal (Saeed et al., 2010b) and as agrochemicals (Xu et al., 2003). As part of our studies in this area, we now describe the synthesis and structure of the title compound, (I).

Structural commentary top

The title compound (Fig. 1) is a benzoyl thio­urea derivative and analogous to a compound recently reported by us (Adam et al., 2014), except that the other substituent is changed to methyl­pyridine and the thio­urea moiety is still in a para position. The dihedral angle between the planes of the benzene and pyridine rings is 26.86 (9)°. The C=O bond length of 1.225 (2) Å is longer than the average C=O bond length (1.200 Å) and comparable to that observed in N-benzoyl-N'-phenyl­thio­urea (Hassan et al., 2008a). The C—N bond lengths are in the range 1.328 (2)–1.417 (2) Å, shorter than the normal single C—N bond length (1.469 Å), indicating partial double-bond character owing to the resonance effect at the carbonyl­thio­urea moiety.

As in most benzoyl thio­urea derivatives, an intra­molecular N—H···O hydrogen bond leads to the formation of an S(6) ring, namely, C7/N1/C8/N2/H2/O1. An intra­molecular C—H···S inter­action (C9/N2/C8/S1/H10/C10) also generates an S(6) ring (Fig. 1, Table 1).

Supra­molecular features top

In the crystal of (I), inversion dimers linked by pairs of N—H···S hydrogen bonds (Table 1, Fig. 2) generate R22(8) loops. As free rotation about the N1—C7 and N2—C8 single bonds is hindered, the C=O and C=S bonds are unlikely to align at the same side of the molecule in order to form a chelate with a metal ion.

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-amino-4-picoline 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 an ethanol solution (Hassan et al., 2008b) as colourless plates (yield 61%).

Refinement top

Crystal data, data collection and structure refinement details are summarized in Table 2. The H-atoms on the N atoms were located in a difference-Fourier map and were fully refined. All other H atoms were positioned geometrically and refined using a riding model with C—H = 0.93–0.96 Å and Uiso(H) = 1.2Ueq(aromatic C) or 1.5Ueq(methyl C).

Related literature top

For related literature, see: Adam et al. (2014); Hassan et al. (2008a, 2008b); Saeed et al. (2010a, 2010b); Xu et al. (2003).

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
[Figure 1] Fig. 1. The molecular structure of the title compound, with 50% probability displacement ellipsoids. Hydrogen bonds are shown as dashed lines.
[Figure 2] Fig. 2. The crystal packing of the title compound viewed down the c axis. Hydrogen bonds are shown as dashed lines.
4-Methyl-N-[(4-methylpyridin-2-yl)carbamothioyl]benzamide top
Crystal data top
C15H15N3OSF(000) = 600
Mr = 285.36Dx = 1.313 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 3960 reflections
a = 11.5297 (12) Åθ = 2.4–25.9°
b = 6.1860 (6) ŵ = 0.22 mm−1
c = 20.657 (2) ÅT = 294 K
β = 101.431 (2)°Plate, colourless
V = 1444.1 (3) Å30.38 × 0.34 × 0.09 mm
Z = 4
Data collection top
Bruker APEXII CCD
diffractometer		4233 independent reflections
Radiation source: fine-focus sealed tube2790 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.028
ϕ and ω scansθmax = 30.1°, θmin = 1.8°
Absorption correction: multi-scan
(SADABS; Bruker, 2005)		h = −16→16
Tmin = 0.920, Tmax = 0.981k = −8→8
15813 measured reflectionsl = −29→29
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.048Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.164H atoms treated by a mixture of independent and constrained refinement
S = 1.05 w = 1/[σ2(Fo2) + (0.0866P)2 + 0.1249P]
where P = (Fo2 + 2Fc2)/3
4233 reflections(Δ/σ)max < 0.001
191 parametersΔρmax = 0.27 e Å−3
0 restraintsΔρmin = −0.19 e Å−3
Crystal data top
C15H15N3OSV = 1444.1 (3) Å3
Mr = 285.36Z = 4
Monoclinic, P21/cMo Kα radiation
a = 11.5297 (12) ŵ = 0.22 mm−1
b = 6.1860 (6) ÅT = 294 K
c = 20.657 (2) Å0.38 × 0.34 × 0.09 mm
β = 101.431 (2)°
Data collection top
Bruker APEXII CCD
diffractometer		4233 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2005)		2790 reflections with I > 2σ(I)
Tmin = 0.920, Tmax = 0.981Rint = 0.028
15813 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0480 restraints
wR(F2) = 0.164H atoms treated by a mixture of independent and constrained refinement
S = 1.05Δρmax = 0.27 e Å−3
4233 reflectionsΔρmin = −0.19 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
xyzUiso*/Ueq
S10.47752 (4)0.82687 (9)0.41107 (2)0.0655 (2)
O10.10758 (10)1.0358 (2)0.43058 (7)0.0664 (4)
N10.30931 (13)1.0520 (2)0.44717 (7)0.0489 (3)
N20.24183 (13)0.7757 (3)0.37524 (7)0.0499 (3)
N30.11827 (13)0.5315 (3)0.31789 (8)0.0656 (4)
C10.11290 (16)1.3270 (3)0.53813 (9)0.0549 (4)
H1A0.05141.22710.53170.066*
C20.11387 (17)1.4947 (3)0.58230 (9)0.0618 (5)
H2A0.05341.50490.60600.074*
C30.20271 (18)1.6472 (3)0.59200 (9)0.0585 (5)
C40.29222 (18)1.6283 (3)0.55643 (9)0.0595 (5)
H4A0.35251.73060.56220.071*
C50.29362 (16)1.4598 (3)0.51247 (8)0.0525 (4)
H5A0.35471.44920.48920.063*
C60.20408 (14)1.3073 (3)0.50317 (8)0.0463 (4)
C70.20039 (14)1.1224 (3)0.45721 (8)0.0481 (4)
C80.33584 (14)0.8813 (3)0.40921 (7)0.0456 (4)
C90.23136 (14)0.5873 (3)0.33544 (7)0.0485 (4)
C100.32251 (15)0.4763 (3)0.31581 (8)0.0546 (4)
H10A0.40040.52240.32920.065*
C110.29672 (18)0.2966 (3)0.27621 (8)0.0549 (4)
C120.18012 (19)0.2358 (4)0.25798 (10)0.0673 (5)
H12A0.15910.11460.23160.081*
C130.0953 (2)0.3570 (4)0.27931 (12)0.0766 (6)
H13A0.01670.31500.26610.092*
C140.2033 (3)1.8322 (4)0.64013 (11)0.0836 (7)
H14A0.27081.92280.63970.125*
H14B0.20731.77540.68380.125*
H14C0.13221.91560.62740.125*
C150.3924 (2)0.1738 (4)0.25264 (13)0.0834 (7)
H15A0.46360.17850.28580.125*
H15B0.40680.23800.21260.125*
H15C0.36820.02620.24430.125*
H1N20.181 (2)0.810 (4)0.3871 (12)0.083 (7)*
H1N10.3673 (18)1.100 (3)0.4720 (10)0.055 (5)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0427 (3)0.0886 (4)0.0651 (3)−0.0032 (2)0.0107 (2)−0.0266 (2)
O10.0437 (7)0.0727 (10)0.0793 (9)0.0008 (6)0.0035 (6)−0.0220 (7)
N10.0440 (7)0.0525 (9)0.0488 (7)−0.0028 (6)0.0057 (6)−0.0086 (6)
N20.0429 (7)0.0548 (9)0.0498 (7)0.0016 (6)0.0040 (6)−0.0088 (6)
N30.0508 (8)0.0691 (11)0.0723 (10)−0.0025 (8)0.0012 (7)−0.0189 (8)
C10.0478 (9)0.0604 (11)0.0555 (9)0.0019 (8)0.0083 (7)−0.0018 (8)
C20.0624 (11)0.0725 (13)0.0510 (9)0.0149 (10)0.0124 (8)−0.0027 (8)
C30.0731 (12)0.0516 (11)0.0464 (9)0.0149 (9)0.0011 (8)0.0002 (7)
C40.0701 (12)0.0457 (10)0.0602 (10)−0.0014 (9)0.0066 (9)0.0008 (8)
C50.0597 (10)0.0466 (10)0.0520 (9)0.0011 (8)0.0127 (7)0.0038 (7)
C60.0475 (8)0.0447 (9)0.0452 (8)0.0044 (7)0.0053 (6)0.0016 (6)
C70.0454 (8)0.0494 (10)0.0480 (8)0.0005 (7)0.0054 (7)−0.0004 (7)
C80.0457 (8)0.0501 (9)0.0401 (7)−0.0016 (7)0.0064 (6)−0.0001 (6)
C90.0495 (9)0.0526 (10)0.0407 (7)−0.0004 (7)0.0029 (6)−0.0006 (7)
C100.0548 (10)0.0566 (11)0.0534 (9)−0.0008 (8)0.0131 (7)−0.0033 (8)
C110.0730 (12)0.0469 (10)0.0460 (8)0.0014 (8)0.0148 (8)0.0007 (7)
C120.0770 (13)0.0601 (12)0.0648 (11)−0.0072 (10)0.0138 (10)−0.0136 (9)
C130.0624 (12)0.0760 (15)0.0862 (14)−0.0093 (10)0.0022 (10)−0.0282 (12)
C140.114 (2)0.0673 (15)0.0669 (13)0.0168 (12)0.0112 (13)−0.0144 (10)
C150.0940 (17)0.0733 (16)0.0907 (16)0.0025 (12)0.0374 (14)−0.0172 (12)
Geometric parameters (Å, º) top
S1—C81.6609 (16)C4—H4A0.9300
O1—C71.225 (2)C5—C61.384 (2)
N1—C71.383 (2)C5—H5A0.9300
N1—C81.385 (2)C6—C71.482 (2)
N1—H1N10.81 (2)C9—C101.382 (2)
N2—C81.339 (2)C10—C111.377 (3)
N2—C91.417 (2)C10—H10A0.9300
N2—H1N20.82 (2)C11—C121.375 (3)
N3—C91.328 (2)C11—C151.498 (3)
N3—C131.337 (3)C12—C131.373 (3)
C1—C21.380 (3)C12—H12A0.9300
C1—C61.394 (2)C13—H13A0.9300
C1—H1A0.9300C14—H14A0.9600
C2—C31.378 (3)C14—H14B0.9600
C2—H2A0.9300C14—H14C0.9600
C3—C41.385 (3)C15—H15A0.9600
C3—C141.515 (3)C15—H15B0.9600
C4—C51.385 (3)C15—H15C0.9600
C7—N1—C8129.34 (15)N2—C8—S1127.11 (13)
C7—N1—H1N1116.6 (14)N1—C8—S1117.91 (12)
C8—N1—H1N1112.9 (14)N3—C9—C10123.61 (16)
C8—N2—C9132.25 (15)N3—C9—N2109.77 (15)
C8—N2—H1N2111.7 (17)C10—C9—N2126.61 (15)
C9—N2—H1N2114.2 (17)C11—C10—C9119.22 (17)
C9—N3—C13116.14 (17)C11—C10—H10A120.4
C2—C1—C6120.01 (18)C9—C10—H10A120.4
C2—C1—H1A120.0C12—C11—C10117.90 (18)
C6—C1—H1A120.0C12—C11—C15121.03 (18)
C3—C2—C1121.29 (17)C10—C11—C15121.07 (19)
C3—C2—H2A119.4C13—C12—C11118.87 (19)
C1—C2—H2A119.4C13—C12—H12A120.6
C2—C3—C4118.38 (17)C11—C12—H12A120.6
C2—C3—C14121.3 (2)N3—C13—C12124.3 (2)
C4—C3—C14120.3 (2)N3—C13—H13A117.9
C5—C4—C3121.21 (18)C12—C13—H13A117.9
C5—C4—H4A119.4C3—C14—H14A109.5
C3—C4—H4A119.4C3—C14—H14B109.5
C6—C5—C4119.94 (17)H14A—C14—H14B109.5
C6—C5—H5A120.0C3—C14—H14C109.5
C4—C5—H5A120.0H14A—C14—H14C109.5
C5—C6—C1119.15 (16)H14B—C14—H14C109.5
C5—C6—C7122.77 (15)C11—C15—H15A109.5
C1—C6—C7118.08 (15)C11—C15—H15B109.5
O1—C7—N1122.22 (16)H15A—C15—H15B109.5
O1—C7—C6122.46 (15)C11—C15—H15C109.5
N1—C7—C6115.31 (15)H15A—C15—H15C109.5
N2—C8—N1114.97 (14)H15B—C15—H15C109.5
C6—C1—C2—C31.2 (3)C9—N2—C8—N1−174.80 (16)
C1—C2—C3—C4−0.3 (3)C9—N2—C8—S14.2 (3)
C1—C2—C3—C14179.57 (18)C7—N1—C8—N23.2 (3)
C2—C3—C4—C5−0.5 (3)C7—N1—C8—S1−175.97 (14)
C14—C3—C4—C5179.64 (17)C13—N3—C9—C100.3 (3)
C3—C4—C5—C60.4 (3)C13—N3—C9—N2179.18 (18)
C4—C5—C6—C10.5 (3)C8—N2—C9—N3173.13 (18)
C4—C5—C6—C7−179.68 (16)C8—N2—C9—C10−8.0 (3)
C2—C1—C6—C5−1.2 (3)N3—C9—C10—C11−0.4 (3)
C2—C1—C6—C7178.91 (16)N2—C9—C10—C11−179.18 (16)
C8—N1—C7—O1−1.1 (3)C9—C10—C11—C120.0 (3)
C8—N1—C7—C6177.94 (15)C9—C10—C11—C15178.80 (19)
C5—C6—C7—O1−152.85 (18)C10—C11—C12—C130.7 (3)
C1—C6—C7—O127.0 (2)C15—C11—C12—C13−178.2 (2)
C5—C6—C7—N128.1 (2)C9—N3—C13—C120.4 (4)
C1—C6—C7—N1−152.03 (16)C11—C12—C13—N3−0.9 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H1N2···O10.82 (2)1.94 (2)2.644 (2)144 (2)
N1—H1N1···S1i0.81 (2)2.74 (2)3.5106 (15)157.8 (18)
C10—H10A···S10.932.573.2211 (19)127
Symmetry code: (i) −x+1, −y+2, −z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H1N2···O10.82 (2)1.94 (2)2.644 (2)144 (2)
N1—H1N1···S1i0.81 (2)2.74 (2)3.5106 (15)157.8 (18)
C10—H10A···S10.932.573.2211 (19)127
Symmetry code: (i) −x+1, −y+2, −z+1.

Experimental details

Crystal data
Chemical formulaC15H15N3OS
Mr285.36
Crystal system, space groupMonoclinic, P21/c
Temperature (K)294
a, b, c (Å)11.5297 (12), 6.1860 (6), 20.657 (2)
β (°) 101.431 (2)
V (Å3)1444.1 (3)
Z4
Radiation typeMo Kα
µ (mm−1)0.22
Crystal size (mm)0.38 × 0.34 × 0.09
Data collection
DiffractometerBruker APEXII CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2005)
Tmin, Tmax0.920, 0.981
No. of measured, independent and
observed [I > 2σ(I)] reflections		15813, 4233, 2790
Rint0.028
(sin θ/λ)max (Å−1)0.706
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.048, 0.164, 1.05
No. of reflections4233
No. of parameters191
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)0.27, −0.19

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

 

Footnotes

‡Additional correspondence author, e-mail: nasertaha90@hotmail.com.

Acknowledgements

The authors would like to thank Universiti Sains Malaysia for a research grant (PKIMIA 846017), which partially supported this work.

References

First citationAdam, F., Ameram, N. & Eltayeb, N. E. (2014). Acta Cryst. E70, o885.  CSD CrossRef IUCr Journals Google Scholar
 First citationBruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
 First citationHassan, I. N., Yamin, B. M. & Kassim, M. B. (2008a). Acta Cryst. E64, o1727.  Web of Science CSD CrossRef IUCr Journals Google Scholar
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 First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationXu, X., Qian, X., Li, Z., Huang, Q. & Chen, G. (2003). J. Fluor. Chem. 121, 51–54.  CrossRef CAS Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

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ISSN: 2056-9890
Volume 71| Part 3| March 2015| Pages 315-317
doi:10.1107/S2056989015003412
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