Crystal structure of 2-methyl-N-[(4-methyl-pyridin-2-yl)carbamo-thio-yl]benzamide.

In the title compound, C15H15N3OS, there is an intra-molecular N-H⋯O hydrogen bond and an intra-molecular C-H⋯S hydrogen bond involving the C=O and C=S bonds which lie on opposite sides of the mol-ecule. The mol-ecule is non-planar with the benzene and pyridine rings being inclined to one another by 26.86 (9)°. In the crystal, mol-ecules are linked by pairs of N-H⋯S hydrogen bonds, forming inversion dimers with an R 2 (2)(8) ring motif. The dimers are linked via C-H⋯S hydrogen bonds, forming slabs parallel to the bc plane.

Related literature

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

Experimental

Crystal data

C15H15N3OS

M = 285.36

Monoclinic,

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

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▸) T min = 0.865, T max = 0.960

15037 measured reflections

3780 independent reflections

3112 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 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

Data collection: APEX2 (Bruker, 2009 ▸); cell refinement: SAINT (Bruker, 2009 ▸); data reduction: SAINT; 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 and PLATON (Spek, 2009 ▸).

Crystal structure: contains datablock(s) I. DOI: 10.1107/S2056989015007860/su5119sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015007860/su5119Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S2056989015007860/su5119Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S2056989015007860/su5119fig1.tif

A view of the mol­ecular structure of the title compound, showing the atom labellling. Displacement ellipsoids are drawn at the 50% probability level.

Click here for additional data file.

b . DOI: 10.1107/S2056989015007860/su5119fig2.tif

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).

CCDC reference: 974439

Additional supporting information: crystallographic information; 3D view; checkCIF report

C15H15N3OS	F(000) = 600
Mr = 285.36	Dx = 1.333 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 11.7131 (3) Å	Cell parameters from 5643 reflections
b = 6.2423 (2) Å	θ = 2.9–30.0°
c = 19.5376 (5) Å	µ = 0.23 mm−1
β = 95.312 (2)°	T = 100 K
V = 1422.39 (7) Å3	Block, colourless
Z = 4	0.54 × 0.28 × 0.18 mm

Bruker SMART APEXII CCD area-detector diffractometer	3780 independent reflections
Radiation source: fine-focus sealed tube	3112 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.031
φ and ω scans	θmax = 29.0°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −15→15
Tmin = 0.865, Tmax = 0.960	k = −8→8
15037 measured reflections	l = −26→26

Refinement on F2	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.037	H 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 reflections	Δρmax = 0.32 e Å−3
191 parameters	Δρmin = −0.23 e Å−3

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.

	x	y	z	Uiso*/Ueq
S1	0.47895 (3)	0.33500 (6)	−0.09032 (2)	0.01997 (10)
O1	0.13144 (8)	0.65482 (17)	−0.07451 (5)	0.0234 (2)
N1	0.32328 (9)	0.59313 (19)	−0.04676 (5)	0.0176 (2)
N2	0.25172 (9)	0.3533 (2)	−0.12933 (6)	0.0193 (2)
N3	0.12736 (10)	0.1758 (2)	−0.20438 (6)	0.0239 (3)
C1	0.13792 (11)	0.8962 (2)	0.05748 (6)	0.0195 (3)
C2	0.14708 (12)	1.0676 (2)	0.10348 (7)	0.0233 (3)
H2A	0.0875	1.0906	0.1325	0.028*
C3	0.24044 (13)	1.2056 (2)	0.10816 (7)	0.0260 (3)
H3A	0.2440	1.3210	0.1400	0.031*
C4	0.32857 (13)	1.1749 (2)	0.06622 (7)	0.0248 (3)
H4A	0.3930	1.2679	0.0695	0.030*
C5	0.32134 (11)	1.0070 (2)	0.01962 (7)	0.0216 (3)
H5A	0.3811	0.9859	−0.0094	0.026*
C6	0.22749 (11)	0.8685 (2)	0.01472 (6)	0.0179 (3)
C7	0.22010 (11)	0.6972 (2)	−0.03910 (6)	0.0179 (3)
C8	0.34405 (10)	0.4251 (2)	−0.09059 (6)	0.0171 (3)
C9	0.23574 (11)	0.1778 (2)	−0.17521 (6)	0.0190 (3)
C10	0.31741 (11)	0.0251 (2)	−0.18797 (7)	0.0205 (3)
H10A	0.3934	0.0348	−0.1665	0.025*
C11	0.28585 (12)	−0.1427 (2)	−0.23287 (7)	0.0218 (3)
C12	0.17278 (13)	−0.1482 (3)	−0.26237 (7)	0.0266 (3)
H12A	0.1474	−0.2611	−0.2926	0.032*
C13	0.09824 (12)	0.0126 (3)	−0.24707 (7)	0.0290 (3)
H13A	0.0218	0.0073	−0.2680	0.035*
C14	0.03709 (12)	0.7467 (3)	0.05661 (7)	0.0247 (3)
H14A	−0.0059	0.7766	0.0962	0.037*
H14B	0.0644	0.5983	0.0589	0.037*
H14C	−0.0129	0.7678	0.0141	0.037*
C15	0.37213 (13)	−0.3085 (3)	−0.24966 (8)	0.0282 (3)
H15A	0.4294	−0.3266	−0.2103	0.042*
H15B	0.4101	−0.2618	−0.2897	0.042*
H15C	0.3331	−0.4452	−0.2599	0.042*
H1N1	0.3827 (15)	0.625 (3)	−0.0167 (9)	0.035 (5)*
H1N2	0.1874 (14)	0.430 (3)	−0.1245 (8)	0.029 (4)*

	U11	U22	U33	U12	U13	U23
S1	0.01482 (15)	0.0247 (2)	0.02041 (15)	−0.00071 (13)	0.00180 (11)	−0.00555 (13)
O1	0.0187 (4)	0.0267 (6)	0.0242 (5)	0.0014 (4)	−0.0009 (4)	−0.0061 (4)
N1	0.0162 (5)	0.0173 (6)	0.0190 (5)	−0.0010 (4)	0.0000 (4)	−0.0034 (4)
N2	0.0157 (5)	0.0211 (6)	0.0209 (5)	0.0004 (5)	0.0007 (4)	−0.0050 (5)
N3	0.0199 (5)	0.0290 (7)	0.0225 (5)	−0.0020 (5)	0.0001 (4)	−0.0070 (5)
C1	0.0210 (6)	0.0193 (7)	0.0178 (6)	0.0018 (5)	−0.0001 (5)	0.0028 (5)
C2	0.0296 (7)	0.0214 (7)	0.0190 (6)	0.0051 (6)	0.0034 (5)	0.0002 (6)
C3	0.0394 (8)	0.0160 (7)	0.0220 (6)	0.0017 (6)	−0.0008 (6)	−0.0020 (5)
C4	0.0304 (7)	0.0160 (7)	0.0275 (7)	−0.0041 (6)	0.0002 (5)	0.0007 (6)
C5	0.0246 (6)	0.0163 (7)	0.0243 (6)	−0.0007 (5)	0.0034 (5)	0.0012 (5)
C6	0.0204 (6)	0.0148 (6)	0.0184 (5)	0.0014 (5)	0.0004 (4)	0.0015 (5)
C7	0.0189 (6)	0.0161 (7)	0.0189 (5)	−0.0004 (5)	0.0035 (4)	0.0016 (5)
C8	0.0179 (6)	0.0173 (7)	0.0165 (5)	−0.0017 (5)	0.0026 (4)	−0.0001 (5)
C9	0.0199 (6)	0.0200 (7)	0.0173 (5)	−0.0045 (5)	0.0026 (4)	−0.0027 (5)
C10	0.0205 (6)	0.0203 (7)	0.0209 (6)	−0.0010 (5)	0.0027 (5)	−0.0024 (5)
C11	0.0292 (7)	0.0200 (7)	0.0172 (6)	−0.0037 (6)	0.0072 (5)	0.0002 (5)
C12	0.0325 (7)	0.0265 (8)	0.0211 (6)	−0.0078 (6)	0.0036 (5)	−0.0077 (6)
C13	0.0242 (7)	0.0363 (9)	0.0259 (7)	−0.0075 (7)	−0.0008 (5)	−0.0098 (7)
C14	0.0231 (6)	0.0287 (8)	0.0229 (6)	−0.0014 (6)	0.0051 (5)	−0.0014 (6)
C15	0.0384 (8)	0.0214 (8)	0.0261 (7)	0.0016 (6)	0.0090 (6)	−0.0033 (6)

S1—C8	1.6768 (13)	C4—H4A	0.9500
O1—C7	1.2223 (15)	C5—C6	1.3949 (19)
N1—C8	1.3898 (17)	C5—H5A	0.9500
N1—C7	1.3924 (16)	C6—C7	1.4964 (18)
N1—H1N1	0.891 (18)	C9—C10	1.3895 (19)
N2—C8	1.3386 (16)	C10—C11	1.3940 (19)
N2—C9	1.4166 (17)	C10—H10A	0.9500
N2—H1N2	0.903 (17)	C11—C12	1.3949 (19)
N3—C13	1.3406 (19)	C11—C15	1.504 (2)
N3—C9	1.3426 (16)	C12—C13	1.381 (2)
C1—C2	1.395 (2)	C12—H12A	0.9500
C1—C6	1.4110 (18)	C13—H13A	0.9500
C1—C14	1.5041 (19)	C14—H14A	0.9800
C2—C3	1.389 (2)	C14—H14B	0.9800
C2—H2A	0.9500	C14—H14C	0.9800
C3—C4	1.389 (2)	C15—H15A	0.9800
C3—H3A	0.9500	C15—H15B	0.9800
C4—C5	1.386 (2)	C15—H15C	0.9800
C8—N1—C7	128.43 (11)	N2—C8—S1	126.96 (11)
C8—N1—H1N1	113.8 (12)	N1—C8—S1	118.02 (9)
C7—N1—H1N1	117.3 (12)	N3—C9—C10	123.84 (12)
C8—N2—C9	132.00 (12)	N3—C9—N2	109.89 (12)
C8—N2—H1N2	113.7 (11)	C10—C9—N2	126.25 (12)
C9—N2—H1N2	114.3 (11)	C9—C10—C11	118.80 (12)
C13—N3—C9	116.57 (13)	C9—C10—H10A	120.6
C2—C1—C6	117.29 (13)	C11—C10—H10A	120.6
C2—C1—C14	119.77 (12)	C10—C11—C12	117.68 (13)
C6—C1—C14	122.91 (12)	C10—C11—C15	120.66 (13)
C3—C2—C1	122.11 (13)	C12—C11—C15	121.65 (13)
C3—C2—H2A	118.9	C13—C12—C11	119.21 (13)
C1—C2—H2A	118.9	C13—C12—H12A	120.4
C2—C3—C4	119.94 (13)	C11—C12—H12A	120.4
C2—C3—H3A	120.0	N3—C13—C12	123.87 (13)
C4—C3—H3A	120.0	N3—C13—H13A	118.1
C5—C4—C3	119.22 (13)	C12—C13—H13A	118.1
C5—C4—H4A	120.4	C1—C14—H14A	109.5
C3—C4—H4A	120.4	C1—C14—H14B	109.5
C4—C5—C6	120.92 (13)	H14A—C14—H14B	109.5
C4—C5—H5A	119.5	C1—C14—H14C	109.5
C6—C5—H5A	119.5	H14A—C14—H14C	109.5
C5—C6—C1	120.51 (12)	H14B—C14—H14C	109.5
C5—C6—C7	119.01 (12)	C11—C15—H15A	109.5
C1—C6—C7	120.39 (12)	C11—C15—H15B	109.5
O1—C7—N1	122.59 (12)	H15A—C15—H15B	109.5
O1—C7—C6	122.90 (12)	C11—C15—H15C	109.5
N1—C7—C6	114.49 (11)	H15A—C15—H15C	109.5
N2—C8—N1	115.02 (11)	H15B—C15—H15C	109.5
C6—C1—C2—C3	−0.6 (2)	C9—N2—C8—N1	−174.26 (13)
C14—C1—C2—C3	177.60 (13)	C9—N2—C8—S1	6.2 (2)
C1—C2—C3—C4	−0.1 (2)	C7—N1—C8—N2	−1.2 (2)
C2—C3—C4—C5	0.6 (2)	C7—N1—C8—S1	178.38 (11)
C3—C4—C5—C6	−0.4 (2)	C13—N3—C9—C10	1.3 (2)
C4—C5—C6—C1	−0.3 (2)	C13—N3—C9—N2	−177.29 (12)
C4—C5—C6—C7	176.50 (12)	C8—N2—C9—N3	−177.61 (14)
C2—C1—C6—C5	0.77 (19)	C8—N2—C9—C10	3.9 (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—C11	177.46 (13)
C14—C1—C6—C7	5.90 (19)	C9—C10—C11—C12	−0.4 (2)
C8—N1—C7—O1	−3.2 (2)	C9—C10—C11—C15	178.39 (13)
C8—N1—C7—C6	178.21 (12)	C10—C11—C12—C13	1.1 (2)
C5—C6—C7—O1	−136.49 (14)	C15—C11—C12—C13	−177.63 (14)
C1—C6—C7—O1	40.29 (19)	C9—N3—C13—C12	−0.5 (2)
C5—C6—C7—N1	42.05 (17)	C11—C12—C13—N3	−0.7 (2)
C1—C6—C7—N1	−141.17 (12)

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

Table 1

Hydrogen-bond geometry (, )

DHA	DH	HA	D A	DHA
N2H1N2O1	0.905(17)	1.863(18)	2.6370(16)	142.2(15)
C10H10AS1	0.95	2.54	3.2084(14)	127
N1H1N1S1i	0.891(18)	2.536(18)	3.4046(11)	165.1(16)
C15H15BS1ii	0.98	2.85	3.8248(16)	175

Symmetry codes: (i) ; (ii) .