1-Benzoyl-3-(6-methyl­pyridin-2-yl)thio­urea

The mol­ecular structure of the title compound, C₁₄H₁₃N₃OS, adopts a cis–trans configuration with respect to the positions of the benzoyl and 6-methyl­pyridin-2yl groups relative to the S atom across the thio­urea C—N bonds. In the crystal structure, the mol­ecules are linked by N—H...S, C—H...S and C—H...O inter­actions, forming a one-dimensional chain parallel to the b axis.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.046
• wR factor = 0.123
• Data-to-parameter ratio = 14.8

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       2.05
PLAT414_ALERT_2_C Short Intra D-H..H-X       H1     ..  H6      ..       1.92 Ang.

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   3 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003).

1-benzoyl-3-(6-methylpyridin-2-yl)thiourea

Crystal data

C14H13N3OS	F(000) = 568
Mr = 271.33	Dx = 1.374 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2710 reflections
a = 7.2687 (14) Å	θ = 2.1–26.0°
b = 18.938 (4) Å	µ = 0.24 mm^−1
c = 10.1216 (19) Å	T = 298 K
β = 109.756 (4)°	Block, colorless
V = 1311.3 (4) Å^3	0.40 × 0.30 × 0.23 mm
Z = 4

Data collection

Bruker SMART APEX CCD area-detector diffractometer	2560 independent reflections
Radiation source: fine-focus sealed tube	2000 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.020
Detector resolution: 83.66 pixels mm^-1	θmax = 26.0°, θmin = 2.1°
ω scans	h = −8→8
Absorption correction: multi-scan (SADABS; Bruker, 2000)	k = −17→23
Tmin = 0.910, Tmax = 0.947	l = −12→11
7196 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.123	H-atom parameters constrained
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0591P)^2 + 0.4366P] where P = (Fo^2 + 2Fc^2)/3
2560 reflections	(Δ/σ)max < 0.001
173 parameters	Δρmax = 0.31 e Å^−3
0 restraints	Δρmin = −0.26 e Å^−3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
S1	0.38212 (11)	0.40652 (3)	0.37926 (5)	0.0709 (3)
O1	0.2225 (3)	0.32957 (8)	0.11006 (16)	0.0757 (5)
N1	0.2776 (2)	0.44799 (8)	0.10831 (15)	0.0478 (4)
H1	0.2673	0.4831	0.0523	0.057*
N2	0.4171 (3)	0.53061 (9)	0.27846 (16)	0.0511 (4)
H2	0.4729	0.5386	0.3667	0.061*
N3	0.3255 (2)	0.58384 (8)	0.05480 (16)	0.0456 (4)
C1	0.1276 (3)	0.38519 (10)	−0.11126 (19)	0.0440 (5)
C2	0.0854 (3)	0.32123 (12)	−0.1815 (2)	0.0573 (6)
H2A	0.1067	0.2793	−0.1307	0.069*
C3	0.0124 (4)	0.31925 (14)	−0.3258 (3)	0.0678 (7)
H3	−0.0134	0.2760	−0.3719	0.081*
C4	−0.0224 (4)	0.38008 (16)	−0.4014 (2)	0.0735 (7)
H4	−0.0708	0.3784	−0.4990	0.088*
C5	0.0138 (5)	0.44367 (15)	−0.3337 (2)	0.0835 (9)
H5	−0.0129	0.4854	−0.3853	0.100*
C6	0.0900 (4)	0.44619 (12)	−0.1890 (2)	0.0649 (7)
H6	0.1161	0.4897	−0.1438	0.078*
C7	0.2111 (3)	0.38328 (10)	0.0447 (2)	0.0468 (5)
C8	0.3570 (3)	0.46294 (10)	0.24818 (19)	0.0474 (5)
C9	0.4058 (3)	0.59044 (10)	0.1934 (2)	0.0432 (5)
C10	0.3162 (3)	0.64204 (11)	−0.0252 (2)	0.0467 (5)
C11	0.3866 (3)	0.70600 (11)	0.0342 (2)	0.0542 (5)
H11	0.3780	0.7454	−0.0224	0.065*
C12	0.4704 (3)	0.71173 (11)	0.1783 (2)	0.0545 (5)
H12	0.5202	0.7547	0.2194	0.065*
C13	0.4791 (3)	0.65334 (10)	0.2598 (2)	0.0499 (5)
H13	0.5328	0.6559	0.3571	0.060*
C14	0.2238 (4)	0.63309 (13)	−0.1806 (2)	0.0612 (6)
H14A	0.2839	0.5941	−0.2110	0.092*
H14B	0.2417	0.6754	−0.2271	0.092*
H14C	0.0866	0.6240	−0.2034	0.092*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.1254 (6)	0.0480 (3)	0.0315 (3)	−0.0015 (3)	0.0161 (3)	0.0069 (2)
O1	0.1233 (15)	0.0449 (9)	0.0472 (9)	−0.0103 (9)	0.0136 (9)	0.0065 (7)
N1	0.0710 (12)	0.0398 (9)	0.0281 (8)	−0.0021 (8)	0.0108 (7)	0.0027 (6)
N2	0.0753 (12)	0.0454 (9)	0.0269 (8)	−0.0035 (8)	0.0097 (7)	0.0014 (7)
N3	0.0556 (10)	0.0456 (9)	0.0335 (8)	−0.0023 (7)	0.0122 (7)	0.0029 (7)
C1	0.0482 (11)	0.0455 (11)	0.0372 (10)	0.0033 (9)	0.0130 (8)	−0.0024 (8)
C2	0.0627 (14)	0.0501 (12)	0.0526 (13)	−0.0055 (10)	0.0109 (10)	−0.0075 (10)
C3	0.0695 (16)	0.0692 (16)	0.0566 (14)	−0.0086 (12)	0.0110 (12)	−0.0242 (12)
C4	0.0847 (18)	0.0894 (19)	0.0353 (12)	0.0033 (15)	0.0057 (11)	−0.0137 (12)
C5	0.130 (2)	0.0685 (17)	0.0378 (13)	0.0090 (16)	0.0091 (14)	0.0043 (11)
C6	0.1004 (19)	0.0488 (13)	0.0371 (11)	0.0064 (12)	0.0121 (11)	−0.0022 (9)
C7	0.0592 (13)	0.0403 (10)	0.0393 (10)	0.0021 (9)	0.0144 (9)	0.0012 (8)
C8	0.0646 (13)	0.0437 (11)	0.0317 (9)	0.0020 (9)	0.0135 (9)	0.0013 (8)
C9	0.0509 (12)	0.0439 (11)	0.0345 (10)	0.0007 (8)	0.0140 (8)	0.0010 (8)
C10	0.0500 (12)	0.0491 (11)	0.0399 (10)	0.0007 (9)	0.0136 (9)	0.0082 (9)
C11	0.0623 (14)	0.0461 (12)	0.0524 (12)	−0.0023 (10)	0.0172 (10)	0.0094 (9)
C12	0.0640 (14)	0.0437 (11)	0.0539 (12)	−0.0038 (10)	0.0176 (10)	−0.0026 (9)
C13	0.0604 (13)	0.0481 (11)	0.0379 (10)	−0.0021 (9)	0.0124 (9)	−0.0038 (9)
C14	0.0796 (16)	0.0596 (14)	0.0389 (11)	−0.0070 (11)	0.0126 (10)	0.0099 (10)

Geometric parameters (Å, º)

S1—C8	1.665 (2)	C4—C5	1.366 (4)
O1—C7	1.201 (2)	C4—H4	0.9300
N1—C8	1.366 (2)	C5—C6	1.381 (3)
N1—C7	1.393 (2)	C5—H5	0.9300
N1—H1	0.8600	C6—H6	0.9300
N2—C8	1.355 (3)	C9—C13	1.383 (3)
N2—C9	1.409 (2)	C10—C11	1.372 (3)
N2—H2	0.8600	C10—C14	1.497 (3)
N3—C9	1.330 (2)	C11—C12	1.382 (3)
N3—C10	1.356 (2)	C11—H11	0.9300
C1—C6	1.372 (3)	C12—C13	1.368 (3)
C1—C2	1.386 (3)	C12—H12	0.9300
C1—C7	1.488 (3)	C13—H13	0.9300
C2—C3	1.375 (3)	C14—H14A	0.9600
C2—H2A	0.9300	C14—H14B	0.9600
C3—C4	1.359 (4)	C14—H14C	0.9600
C3—H3	0.9300
C8—N1—C7	128.36 (16)	O1—C7—C1	122.17 (18)
C8—N1—H1	115.8	N1—C7—C1	114.99 (17)
C7—N1—H1	115.8	N2—C8—N1	114.92 (16)
C8—N2—C9	132.42 (16)	N2—C8—S1	119.12 (14)
C8—N2—H2	113.8	N1—C8—S1	125.95 (15)
C9—N2—H2	113.8	N3—C9—C13	123.59 (18)
C9—N3—C10	117.95 (17)	N3—C9—N2	118.89 (16)
C6—C1—C2	118.36 (19)	C13—C9—N2	117.52 (17)
C6—C1—C7	124.03 (18)	N3—C10—C11	121.35 (18)
C2—C1—C7	117.61 (18)	N3—C10—C14	116.72 (18)
C3—C2—C1	120.5 (2)	C11—C10—C14	121.93 (18)
C3—C2—H2A	119.7	C10—C11—C12	119.85 (19)
C1—C2—H2A	119.7	C10—C11—H11	120.1
C4—C3—C2	120.5 (2)	C12—C11—H11	120.1
C4—C3—H3	119.8	C13—C12—C11	119.14 (19)
C2—C3—H3	119.8	C13—C12—H12	120.4
C3—C4—C5	119.8 (2)	C11—C12—H12	120.4
C3—C4—H4	120.1	C12—C13—C9	118.12 (18)
C5—C4—H4	120.1	C12—C13—H13	120.9
C4—C5—C6	120.2 (2)	C9—C13—H13	120.9
C4—C5—H5	119.9	C10—C14—H14A	109.5
C6—C5—H5	119.9	C10—C14—H14B	109.5
C1—C6—C5	120.7 (2)	H14A—C14—H14B	109.5
C1—C6—H6	119.7	C10—C14—H14C	109.5
C5—C6—H6	119.7	H14A—C14—H14C	109.5
O1—C7—N1	122.83 (18)	H14B—C14—H14C	109.5

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···N3	0.86	1.95	2.676 (2)	141
C6—H6···N1	0.93	2.55	2.853 (2)	100
N2—H2···S1^i	0.86	2.64	3.4831 (18)	167
C12—H12···O1^ii	0.93	2.51	3.364 (3)	153
C13—H13···S1^i	0.93	2.79	3.627 (2)	150

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