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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 71| Part 5| May 2015| Page o356
https://doi.org/10.1107/S2056989015007860

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

Nadiah Ameram,a Farook Adam,a* Nur Nadia Fatihaha and Salih Al-Juaidb

aSchool of Chemical Sciences, Universiti Sains Malaysia, 11800 Georgetown, Penang, Malaysia, and bChemistry Department, Faculty of Science, King Abdulaziz University, Jeddah, Kingdom of Saudi Arabia
*Correspondence e-mail: farook@usm.my

Edited by H. Stoeckli-Evans, University of Neuchâtel, Switzerland (Received 15 April 2015; accepted 21 April 2015; online 30 April 2015)

In the title compound, C15H15N3OS, there is an intra­molecular N—H⋯O hydrogen bond and an intra­molecular C—H⋯S hydrogen bond involving the C=O and C=S bonds which lie on opposite sides of the mol­ecule. The mol­ecule is non-planar with the benzene and pyridine rings being inclined to one another by 26.86 (9)°. In the crystal, mol­ecules are linked by pairs of N—H⋯S hydrogen bonds, forming inversion dimers with an R22(8) ring motif. The dimers are linked via C—H⋯S hydrogen bonds, forming slabs parallel to the bc plane.

CCDC reference: 974439

Similar articles

1. Related literature

For the crystal structures of related compounds, see: Adam et al. (2014[Adam, F., Ameram, N. & Eltayeb, N. E. (2014). Acta Cryst. E70, o885.], 2015[Adam, F., Ameram, N. & Eltayeb, N. E. (2015). Acta Cryst. E71, 315-317.]).

[Scheme 1]

2. Experimental

2.1. Crystal data

  • C15H15N3OS

  • Mr = 285.36

  • Monoclinic, P 21 /c

  • a = 11.7131 (3) Å

  • b = 6.2423 (2) Å

  • c = 19.5376 (5) Å

  • β = 95.312 (2)°

  • V = 1422.39 (7) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.23 mm−1

  • T = 100 K

  • 0.54 × 0.28 × 0.18 mm

2.2. Data collection

  • Bruker SMART APEXII CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.865, Tmax = 0.960

  • 15037 measured reflections

  • 3780 independent reflections

  • 3112 reflections with I > 2σ(I)

  • Rint = 0.031

2.3. Refinement

  • R[F2 > 2σ(F2)] = 0.037

  • wR(F2) = 0.093

  • S = 1.05

  • 3780 reflections

  • 191 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.32 e Å−3

  • Δρmin = −0.23 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
N2—H1N2⋯O1 0.905 (17) 1.863 (18) 2.6370 (16) 142.2 (15)
C10—H10A⋯S1 0.95 2.54 3.2084 (14) 127
N1—H1N1⋯S1i 0.891 (18) 2.536 (18) 3.4046 (11) 165.1 (16)
C15—H15B⋯S1ii 0.98 2.85 3.8248 (16) 175
Symmetry codes: (i) -x+1, -y+1, -z; (ii) [-x+1, y-{\script{1\over 2}}, -z-{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS2013 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015[Sheldrick, G. M. (2015). Acta Cryst. C71, 3-8.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXL2014 and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Supporting information

CCDC reference: 974439

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2056989015007860/su5119sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989015007860/su5119Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2056989015007860/su5119Isup3.cml

checkCIF report


Structural commentary top

The title compound shows the bond lengths and angles which are generally normal in N-alkyl-N'-benzoyl­thio­urea compounds. The bond length of the carbonyl [C8—O1 = 1.229 (15) Å] group of the compound have typical double-bond character, as shown in two closely related compounds, viz. 4-methyl-N-[(4-methyl­pyridin-2-yl)carbamo­thioyl]benzamide (Adam et al., 2015) and 4-methyl-N-[2-(pyridin-2-yl)ethyl­carbamo­thioyl]benzamide (Adam et al., 2014). However, the thio­carbonyl­group [C9—S1 = 1.6755 (13) Å] is longer than the typical C═S of 1.660 (2) Å. The C—N bond lengths are all shorter than the average single C—N bond length of 1.472 (5) Å, being C8—N1 = 1.3930 (16) Å, C9—N1 = 1.3915 (16) Å, C10—N3 = 1.3411 (16) Å and C10—N2 = 1.4157 (16) Å, thus showing varying degrees of single-bond character. There are two intra­molecular hydrogen bonds, viz. C11—H11–S1 and N2—H2–O1, which have lengths of 3.2051 (13) and 2.6372 (14) Å, respectively (Table 1). The bond character of the structure is presumed to be the result of the intra­molecular hydrogen bonding that `locks' the molecule into a pseudo-planar six-membered ring structure, similar to structure of the 4-methyl derivative mentioned above (Adam et al., 2015). These results are in agreement with the expected delocalisation in the compound and confirmed by bond angles C9—N2—C10 = 132.02 (11)° and C9—N1—C8 = 128.54 (10)°, indicating sp2 hybridization of atoms N1 and N2.

In the crystal, molecules are linked by a pair of N—H···S hydrogen bonds forming inversion dimers with an R22(8) ring motif (Table 1 and Fig. 2). This situation is similar to that in the 4-methyl derivative mentioned above (Adam et al., 2015). The dimers are linked via C—H···S hydrogen bonds forming slabs parallel to the bc plane.

Synthesis and crystallization top

o-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 titration, washed several times with a cold ethanol/water mixture and purified by recrystallization from an ethanol solution (m.p. 437.9–438.8 K). FT–IR (KBr, cm-1) analysis shows the following vibrational frequencies for N—H, C═O, C—N and C═S at 3237, 1683, 1329 and 1157, respectively. 1H NMR results show chemical shifts at 9.545 and 13.501 p.p.m. for the two N—H protons.

Refinement top

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

Related literature top

For the crystal structures of related compounds, see: Adam et al. (2014, 2015).

Structure description top

The title compound shows the bond lengths and angles which are generally normal in N-alkyl-N'-benzoyl­thio­urea compounds. The bond length of the carbonyl [C8—O1 = 1.229 (15) Å] group of the compound have typical double-bond character, as shown in two closely related compounds, viz. 4-methyl-N-[(4-methyl­pyridin-2-yl)carbamo­thioyl]benzamide (Adam et al., 2015) and 4-methyl-N-[2-(pyridin-2-yl)ethyl­carbamo­thioyl]benzamide (Adam et al., 2014). However, the thio­carbonyl­group [C9—S1 = 1.6755 (13) Å] is longer than the typical C═S of 1.660 (2) Å. The C—N bond lengths are all shorter than the average single C—N bond length of 1.472 (5) Å, being C8—N1 = 1.3930 (16) Å, C9—N1 = 1.3915 (16) Å, C10—N3 = 1.3411 (16) Å and C10—N2 = 1.4157 (16) Å, thus showing varying degrees of single-bond character. There are two intra­molecular hydrogen bonds, viz. C11—H11–S1 and N2—H2–O1, which have lengths of 3.2051 (13) and 2.6372 (14) Å, respectively (Table 1). The bond character of the structure is presumed to be the result of the intra­molecular hydrogen bonding that `locks' the molecule into a pseudo-planar six-membered ring structure, similar to structure of the 4-methyl derivative mentioned above (Adam et al., 2015). These results are in agreement with the expected delocalisation in the compound and confirmed by bond angles C9—N2—C10 = 132.02 (11)° and C9—N1—C8 = 128.54 (10)°, indicating sp2 hybridization of atoms N1 and N2.

In the crystal, molecules are linked by a pair of N—H···S hydrogen bonds forming inversion dimers with an R22(8) ring motif (Table 1 and Fig. 2). This situation is similar to that in the 4-methyl derivative mentioned above (Adam et al., 2015). The dimers are linked via C—H···S hydrogen bonds forming slabs parallel to the bc plane.

For the crystal structures of related compounds, see: Adam et al. (2014, 2015).

Synthesis and crystallization top

o-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 titration, washed several times with a cold ethanol/water mixture and purified by recrystallization from an ethanol solution (m.p. 437.9–438.8 K). FT–IR (KBr, cm-1) analysis shows the following vibrational frequencies for N—H, C═O, C—N and C═S at 3237, 1683, 1329 and 1157, respectively. 1H NMR results show chemical shifts at 9.545 and 13.501 p.p.m. for the two N—H protons.

Refinement details top

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

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS2013 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015) and PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. A view of the molecular structure of the title compound, showing the atom labellling. Displacement ellipsoids are drawn at the 50% probability level.
[Figure 2] Fig. 2. A view along the b axis of the crystal packing of the title compound. Hydrogen bonds are shown as dashed lines (see Table 1 for details).
2-Methyl-N-[(4-methylpyridin-2-yl)carbamothioyl]benzamide top
Crystal data top
C15H15N3OSF(000) = 600
Mr = 285.36Dx = 1.333 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 11.7131 (3) ÅCell parameters from 5643 reflections
b = 6.2423 (2) Åθ = 2.9–30.0°
c = 19.5376 (5) ŵ = 0.23 mm−1
β = 95.312 (2)°T = 100 K
V = 1422.39 (7) Å3Block, colourless
Z = 40.54 × 0.28 × 0.18 mm
Data collection top
Bruker SMART APEXII CCD area-detector
diffractometer		3780 independent reflections
Radiation source: fine-focus sealed tube3112 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.031
φ and ω scansθmax = 29.0°, θmin = 1.8°
Absorption correction: multi-scan
(SADABS; Bruker, 2009)		h = −15→15
Tmin = 0.865, Tmax = 0.960k = −8→8
15037 measured reflectionsl = −26→26
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.037H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.093 w = 1/[σ2(Fo2) + (0.0369P)2 + 0.6623P]
where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max < 0.001
3780 reflectionsΔρmax = 0.32 e Å−3
191 parametersΔρmin = −0.23 e Å−3
Crystal data top
C15H15N3OSV = 1422.39 (7) Å3
Mr = 285.36Z = 4
Monoclinic, P21/cMo Kα radiation
a = 11.7131 (3) ŵ = 0.23 mm−1
b = 6.2423 (2) ÅT = 100 K
c = 19.5376 (5) Å0.54 × 0.28 × 0.18 mm
β = 95.312 (2)°
Data collection top
Bruker SMART APEXII CCD area-detector
diffractometer		3780 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2009)		3112 reflections with I > 2σ(I)
Tmin = 0.865, Tmax = 0.960Rint = 0.031
15037 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0370 restraints
wR(F2) = 0.093H atoms treated by a mixture of independent and constrained refinement
S = 1.05Δρmax = 0.32 e Å−3
3780 reflectionsΔρmin = −0.23 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S10.47895 (3)0.33500 (6)−0.09032 (2)0.01997 (10)
O10.13144 (8)0.65482 (17)−0.07451 (5)0.0234 (2)
N10.32328 (9)0.59313 (19)−0.04676 (5)0.0176 (2)
N20.25172 (9)0.3533 (2)−0.12933 (6)0.0193 (2)
N30.12736 (10)0.1758 (2)−0.20438 (6)0.0239 (3)
C10.13792 (11)0.8962 (2)0.05748 (6)0.0195 (3)
C20.14708 (12)1.0676 (2)0.10348 (7)0.0233 (3)
H2A0.08751.09060.13250.028*
C30.24044 (13)1.2056 (2)0.10816 (7)0.0260 (3)
H3A0.24401.32100.14000.031*
C40.32857 (13)1.1749 (2)0.06622 (7)0.0248 (3)
H4A0.39301.26790.06950.030*
C50.32134 (11)1.0070 (2)0.01962 (7)0.0216 (3)
H5A0.38110.9859−0.00940.026*
C60.22749 (11)0.8685 (2)0.01472 (6)0.0179 (3)
C70.22010 (11)0.6972 (2)−0.03910 (6)0.0179 (3)
C80.34405 (10)0.4251 (2)−0.09059 (6)0.0171 (3)
C90.23574 (11)0.1778 (2)−0.17521 (6)0.0190 (3)
C100.31741 (11)0.0251 (2)−0.18797 (7)0.0205 (3)
H10A0.39340.0348−0.16650.025*
C110.28585 (12)−0.1427 (2)−0.23287 (7)0.0218 (3)
C120.17278 (13)−0.1482 (3)−0.26237 (7)0.0266 (3)
H12A0.1474−0.2611−0.29260.032*
C130.09824 (12)0.0126 (3)−0.24707 (7)0.0290 (3)
H13A0.02180.0073−0.26800.035*
C140.03709 (12)0.7467 (3)0.05661 (7)0.0247 (3)
H14A−0.00590.77660.09620.037*
H14B0.06440.59830.05890.037*
H14C−0.01290.76780.01410.037*
C150.37213 (13)−0.3085 (3)−0.24966 (8)0.0282 (3)
H15A0.4294−0.3266−0.21030.042*
H15B0.4101−0.2618−0.28970.042*
H15C0.3331−0.4452−0.25990.042*
H1N10.3827 (15)0.625 (3)−0.0167 (9)0.035 (5)*
H1N20.1874 (14)0.430 (3)−0.1245 (8)0.029 (4)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.01482 (15)0.0247 (2)0.02041 (15)−0.00071 (13)0.00180 (11)−0.00555 (13)
O10.0187 (4)0.0267 (6)0.0242 (5)0.0014 (4)−0.0009 (4)−0.0061 (4)
N10.0162 (5)0.0173 (6)0.0190 (5)−0.0010 (4)0.0000 (4)−0.0034 (4)
N20.0157 (5)0.0211 (6)0.0209 (5)0.0004 (5)0.0007 (4)−0.0050 (5)
N30.0199 (5)0.0290 (7)0.0225 (5)−0.0020 (5)0.0001 (4)−0.0070 (5)
C10.0210 (6)0.0193 (7)0.0178 (6)0.0018 (5)−0.0001 (5)0.0028 (5)
C20.0296 (7)0.0214 (7)0.0190 (6)0.0051 (6)0.0034 (5)0.0002 (6)
C30.0394 (8)0.0160 (7)0.0220 (6)0.0017 (6)−0.0008 (6)−0.0020 (5)
C40.0304 (7)0.0160 (7)0.0275 (7)−0.0041 (6)0.0002 (5)0.0007 (6)
C50.0246 (6)0.0163 (7)0.0243 (6)−0.0007 (5)0.0034 (5)0.0012 (5)
C60.0204 (6)0.0148 (6)0.0184 (5)0.0014 (5)0.0004 (4)0.0015 (5)
C70.0189 (6)0.0161 (7)0.0189 (5)−0.0004 (5)0.0035 (4)0.0016 (5)
C80.0179 (6)0.0173 (7)0.0165 (5)−0.0017 (5)0.0026 (4)−0.0001 (5)
C90.0199 (6)0.0200 (7)0.0173 (5)−0.0045 (5)0.0026 (4)−0.0027 (5)
C100.0205 (6)0.0203 (7)0.0209 (6)−0.0010 (5)0.0027 (5)−0.0024 (5)
C110.0292 (7)0.0200 (7)0.0172 (6)−0.0037 (6)0.0072 (5)0.0002 (5)
C120.0325 (7)0.0265 (8)0.0211 (6)−0.0078 (6)0.0036 (5)−0.0077 (6)
C130.0242 (7)0.0363 (9)0.0259 (7)−0.0075 (7)−0.0008 (5)−0.0098 (7)
C140.0231 (6)0.0287 (8)0.0229 (6)−0.0014 (6)0.0051 (5)−0.0014 (6)
C150.0384 (8)0.0214 (8)0.0261 (7)0.0016 (6)0.0090 (6)−0.0033 (6)
Geometric parameters (Å, º) top
S1—C81.6768 (13)C4—H4A0.9500
O1—C71.2223 (15)C5—C61.3949 (19)
N1—C81.3898 (17)C5—H5A0.9500
N1—C71.3924 (16)C6—C71.4964 (18)
N1—H1N10.891 (18)C9—C101.3895 (19)
N2—C81.3386 (16)C10—C111.3940 (19)
N2—C91.4166 (17)C10—H10A0.9500
N2—H1N20.903 (17)C11—C121.3949 (19)
N3—C131.3406 (19)C11—C151.504 (2)
N3—C91.3426 (16)C12—C131.381 (2)
C1—C21.395 (2)C12—H12A0.9500
C1—C61.4110 (18)C13—H13A0.9500
C1—C141.5041 (19)C14—H14A0.9800
C2—C31.389 (2)C14—H14B0.9800
C2—H2A0.9500C14—H14C0.9800
C3—C41.389 (2)C15—H15A0.9800
C3—H3A0.9500C15—H15B0.9800
C4—C51.386 (2)C15—H15C0.9800
C8—N1—C7128.43 (11)N2—C8—S1126.96 (11)
C8—N1—H1N1113.8 (12)N1—C8—S1118.02 (9)
C7—N1—H1N1117.3 (12)N3—C9—C10123.84 (12)
C8—N2—C9132.00 (12)N3—C9—N2109.89 (12)
C8—N2—H1N2113.7 (11)C10—C9—N2126.25 (12)
C9—N2—H1N2114.3 (11)C9—C10—C11118.80 (12)
C13—N3—C9116.57 (13)C9—C10—H10A120.6
C2—C1—C6117.29 (13)C11—C10—H10A120.6
C2—C1—C14119.77 (12)C10—C11—C12117.68 (13)
C6—C1—C14122.91 (12)C10—C11—C15120.66 (13)
C3—C2—C1122.11 (13)C12—C11—C15121.65 (13)
C3—C2—H2A118.9C13—C12—C11119.21 (13)
C1—C2—H2A118.9C13—C12—H12A120.4
C2—C3—C4119.94 (13)C11—C12—H12A120.4
C2—C3—H3A120.0N3—C13—C12123.87 (13)
C4—C3—H3A120.0N3—C13—H13A118.1
C5—C4—C3119.22 (13)C12—C13—H13A118.1
C5—C4—H4A120.4C1—C14—H14A109.5
C3—C4—H4A120.4C1—C14—H14B109.5
C4—C5—C6120.92 (13)H14A—C14—H14B109.5
C4—C5—H5A119.5C1—C14—H14C109.5
C6—C5—H5A119.5H14A—C14—H14C109.5
C5—C6—C1120.51 (12)H14B—C14—H14C109.5
C5—C6—C7119.01 (12)C11—C15—H15A109.5
C1—C6—C7120.39 (12)C11—C15—H15B109.5
O1—C7—N1122.59 (12)H15A—C15—H15B109.5
O1—C7—C6122.90 (12)C11—C15—H15C109.5
N1—C7—C6114.49 (11)H15A—C15—H15C109.5
N2—C8—N1115.02 (11)H15B—C15—H15C109.5
C6—C1—C2—C3−0.6 (2)C9—N2—C8—N1−174.26 (13)
C14—C1—C2—C3177.60 (13)C9—N2—C8—S16.2 (2)
C1—C2—C3—C4−0.1 (2)C7—N1—C8—N2−1.2 (2)
C2—C3—C4—C50.6 (2)C7—N1—C8—S1178.38 (11)
C3—C4—C5—C6−0.4 (2)C13—N3—C9—C101.3 (2)
C4—C5—C6—C1−0.3 (2)C13—N3—C9—N2−177.29 (12)
C4—C5—C6—C7176.50 (12)C8—N2—C9—N3−177.61 (14)
C2—C1—C6—C50.77 (19)C8—N2—C9—C103.9 (2)
C14—C1—C6—C5−177.37 (12)N3—C9—C10—C11−0.9 (2)
C2—C1—C6—C7−175.96 (12)N2—C9—C10—C11177.46 (13)
C14—C1—C6—C75.90 (19)C9—C10—C11—C12−0.4 (2)
C8—N1—C7—O1−3.2 (2)C9—C10—C11—C15178.39 (13)
C8—N1—C7—C6178.21 (12)C10—C11—C12—C131.1 (2)
C5—C6—C7—O1−136.49 (14)C15—C11—C12—C13−177.63 (14)
C1—C6—C7—O140.29 (19)C9—N3—C13—C12−0.5 (2)
C5—C6—C7—N142.05 (17)C11—C12—C13—N3−0.7 (2)
C1—C6—C7—N1−141.17 (12)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H1N2···O10.905 (17)1.863 (18)2.6370 (16)142.2 (15)
C10—H10A···S10.952.543.2084 (14)127
N1—H1N1···S1i0.891 (18)2.536 (18)3.4046 (11)165.1 (16)
C15—H15B···S1ii0.982.853.8248 (16)175
Symmetry codes: (i) −x+1, −y+1, −z; (ii) −x+1, y−1/2, −z−1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H1N2···O10.905 (17)1.863 (18)2.6370 (16)142.2 (15)
C10—H10A···S10.952.543.2084 (14)127
N1—H1N1···S1i0.891 (18)2.536 (18)3.4046 (11)165.1 (16)
C15—H15B···S1ii0.982.853.8248 (16)175
Symmetry codes: (i) −x+1, −y+1, −z; (ii) −x+1, y−1/2, −z−1/2.
 

Acknowledgements

This work was supported in part by a research grant (PKIMIA 846017) from the Universiti Sains Malaysia (USM).

References

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 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS 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

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ISSN: 2056-9890
Volume 71| Part 5| May 2015| Page o356
https://doi.org/10.1107/S2056989015007860
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