Buy article online - an online subscription or single-article purchase is required to access this article.
organic compounds
The title molecule, C15H15N3OS, adopts a cis–trans configuration with respect to the positions of the 3-methylbenzoyl and 6-methyl-2-pyridyl groups relative to the S atom across the thiourea C—N bonds. In the crystal structure, the molecules are linked by intermolecular N—HS hydrogen bonds, forming centrosymmetric dimers.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806025414/bh2029sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806025414/bh2029Isup2.hkl |
CCDC reference: 618776
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.003 Å
- R factor = 0.045
- wR factor = 0.132
- Data-to-parameter ratio = 13.4
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ? PLAT230_ALERT_2_C Hirshfeld Test Diff for S1 - C8 .. 6.77 su
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 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 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
Computing details top
Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL (Sheldrick, 1997); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, PARST95 (Nardelli, 1995) and PLATON (Spek, 2003).
1-(3-Methylbenzoyl)-3-(6-methyl-2-pyridyl)thiourea top
Crystal data top
C15H15N3OS | F(000) = 600 |
Mr = 285.36 | Dx = 1.354 Mg m−3 |
Monoclinic, P21/n | Melting point = 489.3–491.7 K |
Hall symbol: -P 2yn | Mo Kα radiation, λ = 0.71073 Å |
a = 7.1981 (19) Å | Cell parameters from 2524 reflections |
b = 10.092 (3) Å | θ = 2.1–25.0° |
c = 19.372 (5) Å | µ = 0.23 mm−1 |
β = 95.826 (5)° | T = 298 K |
V = 1399.9 (6) Å3 | Block, colourless |
Z = 4 | 0.50 × 0.32 × 0.28 mm |
Data collection top
Bruker SMART APEX CCD area-detector diffractometer | 2459 independent reflections |
Radiation source: fine-focus sealed tube | 1995 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.020 |
Detector resolution: 83.66 pixels mm-1 | θmax = 25.0°, θmin = 2.1° |
ω scans | h = −8→8 |
Absorption correction: multi-scan (SADABS; Bruker, 2000) | k = −8→12 |
Tmin = 0.893, Tmax = 0.938 | l = −20→23 |
6913 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)] = 0.045 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.132 | H-atom parameters constrained |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0823P)2 + 0.2335P] where P = (Fo2 + 2Fc2)/3 |
2459 reflections | (Δ/σ)max < 0.001 |
183 parameters | Δρmax = 0.26 e Å−3 |
0 restraints | Δρmin = −0.14 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
S1 | 0.57143 (10) | −0.15632 (6) | 0.07052 (3) | 0.0612 (3) | |
O1 | 0.5921 (3) | −0.27604 (16) | 0.21202 (8) | 0.0688 (5) | |
N1 | 0.5519 (2) | −0.05276 (16) | 0.19781 (8) | 0.0451 (4) | |
H1A | 0.5420 | 0.0191 | 0.2210 | 0.054* | |
N2 | 0.4742 (2) | 0.08305 (16) | 0.10422 (8) | 0.0451 (4) | |
H2A | 0.4583 | 0.0900 | 0.0598 | 0.054* | |
N3 | 0.4379 (2) | 0.19609 (17) | 0.20855 (8) | 0.0434 (4) | |
C1 | 0.5814 (3) | −0.2493 (2) | 0.35613 (11) | 0.0473 (5) | |
H1 | 0.5504 | −0.3313 | 0.3363 | 0.057* | |
C2 | 0.5970 (3) | −0.2361 (2) | 0.42806 (11) | 0.0514 (5) | |
C3 | 0.6451 (3) | −0.1137 (3) | 0.45560 (12) | 0.0609 (6) | |
H3 | 0.6566 | −0.1028 | 0.5035 | 0.073* | |
C4 | 0.6768 (3) | −0.0072 (2) | 0.41426 (12) | 0.0626 (6) | |
H4 | 0.7091 | 0.0745 | 0.4343 | 0.075* | |
C5 | 0.6607 (3) | −0.0211 (2) | 0.34328 (11) | 0.0493 (5) | |
H5 | 0.6832 | 0.0509 | 0.3153 | 0.059* | |
C6 | 0.6110 (3) | −0.1427 (2) | 0.31344 (10) | 0.0421 (5) | |
C7 | 0.5873 (3) | −0.16645 (19) | 0.23729 (11) | 0.0451 (5) | |
C8 | 0.5306 (3) | −0.0389 (2) | 0.12747 (10) | 0.0425 (5) | |
C9 | 0.4371 (3) | 0.20047 (19) | 0.14009 (10) | 0.0401 (5) | |
C10 | 0.4054 (3) | 0.3097 (2) | 0.24273 (11) | 0.0460 (5) | |
C11 | 0.3720 (3) | 0.4268 (2) | 0.20764 (12) | 0.0529 (5) | |
H11 | 0.3505 | 0.5040 | 0.2318 | 0.064* | |
C12 | 0.3706 (3) | 0.4296 (2) | 0.13732 (12) | 0.0575 (6) | |
H12 | 0.3478 | 0.5089 | 0.1134 | 0.069* | |
C13 | 0.4027 (3) | 0.3156 (2) | 0.10149 (11) | 0.0491 (5) | |
H13 | 0.4014 | 0.3155 | 0.0534 | 0.059* | |
C14 | 0.5593 (4) | −0.3522 (3) | 0.47304 (14) | 0.0730 (8) | |
H14A | 0.4423 | −0.3394 | 0.4919 | 0.110* | |
H14B | 0.6576 | −0.3595 | 0.5102 | 0.110* | |
H14C | 0.5540 | −0.4318 | 0.4458 | 0.110* | |
C15 | 0.4109 (4) | 0.3003 (3) | 0.31996 (12) | 0.0619 (6) | |
H15A | 0.3276 | 0.2316 | 0.3319 | 0.093* | |
H15B | 0.3728 | 0.3833 | 0.3382 | 0.093* | |
H15C | 0.5357 | 0.2799 | 0.3393 | 0.093* |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0963 (5) | 0.0509 (4) | 0.0370 (3) | 0.0203 (3) | 0.0104 (3) | −0.0046 (2) |
O1 | 0.1155 (15) | 0.0417 (9) | 0.0500 (9) | 0.0152 (9) | 0.0128 (9) | −0.0015 (7) |
N1 | 0.0639 (11) | 0.0390 (9) | 0.0329 (8) | 0.0067 (8) | 0.0072 (7) | −0.0011 (7) |
N2 | 0.0588 (11) | 0.0442 (10) | 0.0322 (8) | 0.0081 (8) | 0.0036 (7) | −0.0003 (7) |
N3 | 0.0484 (10) | 0.0430 (10) | 0.0393 (9) | 0.0041 (7) | 0.0069 (7) | −0.0031 (7) |
C1 | 0.0510 (12) | 0.0440 (12) | 0.0472 (12) | 0.0020 (9) | 0.0060 (9) | 0.0033 (9) |
C2 | 0.0490 (12) | 0.0577 (14) | 0.0486 (12) | 0.0064 (10) | 0.0109 (9) | 0.0146 (10) |
C3 | 0.0714 (15) | 0.0698 (16) | 0.0410 (12) | 0.0017 (12) | 0.0036 (10) | −0.0026 (12) |
C4 | 0.0793 (16) | 0.0548 (14) | 0.0526 (13) | −0.0077 (12) | 0.0008 (11) | −0.0065 (11) |
C5 | 0.0546 (12) | 0.0460 (12) | 0.0468 (11) | −0.0031 (10) | 0.0022 (9) | 0.0028 (10) |
C6 | 0.0385 (10) | 0.0455 (11) | 0.0430 (11) | 0.0052 (9) | 0.0071 (8) | 0.0051 (9) |
C7 | 0.0529 (12) | 0.0398 (11) | 0.0434 (11) | 0.0086 (9) | 0.0089 (9) | 0.0017 (9) |
C8 | 0.0456 (11) | 0.0454 (11) | 0.0365 (10) | 0.0034 (9) | 0.0051 (8) | 0.0014 (9) |
C9 | 0.0392 (10) | 0.0418 (11) | 0.0393 (11) | 0.0019 (8) | 0.0036 (8) | −0.0026 (9) |
C10 | 0.0420 (11) | 0.0496 (12) | 0.0465 (12) | 0.0027 (9) | 0.0053 (8) | −0.0096 (9) |
C11 | 0.0558 (13) | 0.0426 (12) | 0.0606 (14) | 0.0061 (10) | 0.0068 (10) | −0.0084 (10) |
C12 | 0.0676 (15) | 0.0420 (12) | 0.0623 (14) | 0.0082 (11) | 0.0040 (11) | 0.0044 (11) |
C13 | 0.0569 (13) | 0.0475 (12) | 0.0420 (11) | 0.0037 (10) | 0.0014 (9) | 0.0031 (9) |
C14 | 0.0856 (19) | 0.0761 (18) | 0.0584 (15) | −0.0036 (14) | 0.0127 (13) | 0.0217 (13) |
C15 | 0.0740 (16) | 0.0637 (15) | 0.0487 (13) | 0.0120 (12) | 0.0094 (11) | −0.0112 (11) |
Geometric parameters (Å, º) top
S1—C8 | 1.665 (2) | C4—H4 | 0.9300 |
O1—C7 | 1.211 (2) | C5—C6 | 1.388 (3) |
N1—C8 | 1.363 (2) | C5—H5 | 0.9300 |
N1—C7 | 1.388 (2) | C6—C7 | 1.487 (3) |
N1—H1A | 0.8600 | C9—C13 | 1.390 (3) |
N2—C8 | 1.359 (3) | C10—C11 | 1.372 (3) |
N2—C9 | 1.413 (2) | C10—C15 | 1.496 (3) |
N2—H2A | 0.8600 | C11—C12 | 1.362 (3) |
N3—C9 | 1.326 (3) | C11—H11 | 0.9300 |
N3—C10 | 1.356 (3) | C12—C13 | 1.376 (3) |
C1—C6 | 1.386 (3) | C12—H12 | 0.9300 |
C1—C2 | 1.393 (3) | C13—H13 | 0.9300 |
C1—H1 | 0.9300 | C14—H14A | 0.9600 |
C2—C3 | 1.376 (3) | C14—H14B | 0.9600 |
C2—C14 | 1.501 (3) | C14—H14C | 0.9600 |
C3—C4 | 1.373 (3) | C15—H15A | 0.9600 |
C3—H3 | 0.9300 | C15—H15B | 0.9600 |
C4—C5 | 1.375 (3) | C15—H15C | 0.9600 |
C8—N1—C7 | 129.14 (17) | N2—C8—S1 | 119.47 (14) |
C8—N1—H1A | 115.4 | N1—C8—S1 | 125.46 (15) |
C7—N1—H1A | 115.4 | N3—C9—C13 | 123.24 (18) |
C8—N2—C9 | 131.45 (16) | N3—C9—N2 | 118.82 (17) |
C8—N2—H2A | 114.3 | C13—C9—N2 | 117.94 (17) |
C9—N2—H2A | 114.3 | N3—C10—C11 | 121.09 (19) |
C9—N3—C10 | 118.45 (18) | N3—C10—C15 | 116.49 (19) |
C6—C1—C2 | 121.4 (2) | C11—C10—C15 | 122.4 (2) |
C6—C1—H1 | 119.3 | C12—C11—C10 | 119.8 (2) |
C2—C1—H1 | 119.3 | C12—C11—H11 | 120.1 |
C3—C2—C1 | 117.7 (2) | C10—C11—H11 | 120.1 |
C3—C2—C14 | 121.9 (2) | C11—C12—C13 | 120.2 (2) |
C1—C2—C14 | 120.3 (2) | C11—C12—H12 | 119.9 |
C4—C3—C2 | 121.8 (2) | C13—C12—H12 | 119.9 |
C4—C3—H3 | 119.1 | C12—C13—C9 | 117.2 (2) |
C2—C3—H3 | 119.1 | C12—C13—H13 | 121.4 |
C3—C4—C5 | 120.1 (2) | C9—C13—H13 | 121.4 |
C3—C4—H4 | 120.0 | C2—C14—H14A | 109.5 |
C5—C4—H4 | 120.0 | C2—C14—H14B | 109.5 |
C4—C5—C6 | 119.9 (2) | H14A—C14—H14B | 109.5 |
C4—C5—H5 | 120.0 | C2—C14—H14C | 109.5 |
C6—C5—H5 | 120.0 | H14A—C14—H14C | 109.5 |
C1—C6—C5 | 119.08 (19) | H14B—C14—H14C | 109.5 |
C1—C6—C7 | 117.27 (18) | C10—C15—H15A | 109.5 |
C5—C6—C7 | 123.65 (18) | C10—C15—H15B | 109.5 |
O1—C7—N1 | 122.89 (19) | H15A—C15—H15B | 109.5 |
O1—C7—C6 | 122.87 (18) | C10—C15—H15C | 109.5 |
N1—C7—C6 | 114.19 (17) | H15A—C15—H15C | 109.5 |
N2—C8—N1 | 115.07 (17) | H15B—C15—H15C | 109.5 |
C6—C1—C2—C3 | −0.7 (3) | C9—N2—C8—N1 | 1.6 (3) |
C6—C1—C2—C14 | 178.4 (2) | C9—N2—C8—S1 | −177.29 (16) |
C1—C2—C3—C4 | 0.1 (3) | C7—N1—C8—N2 | 172.2 (2) |
C14—C2—C3—C4 | −179.0 (2) | C7—N1—C8—S1 | −8.9 (3) |
C2—C3—C4—C5 | 0.0 (4) | C10—N3—C9—C13 | −0.6 (3) |
C3—C4—C5—C6 | 0.5 (3) | C10—N3—C9—N2 | 178.88 (16) |
C2—C1—C6—C5 | 1.2 (3) | C8—N2—C9—N3 | −7.2 (3) |
C2—C1—C6—C7 | −178.85 (18) | C8—N2—C9—C13 | 172.3 (2) |
C4—C5—C6—C1 | −1.1 (3) | C9—N3—C10—C11 | 0.1 (3) |
C4—C5—C6—C7 | 179.0 (2) | C9—N3—C10—C15 | −179.01 (18) |
C8—N1—C7—O1 | −5.2 (4) | N3—C10—C11—C12 | 0.3 (3) |
C8—N1—C7—C6 | 177.25 (19) | C15—C10—C11—C12 | 179.3 (2) |
C1—C6—C7—O1 | −19.6 (3) | C10—C11—C12—C13 | −0.1 (3) |
C5—C6—C7—O1 | 160.3 (2) | C11—C12—C13—C9 | −0.4 (3) |
C1—C6—C7—N1 | 157.93 (18) | N3—C9—C13—C12 | 0.8 (3) |
C5—C6—C7—N1 | −22.2 (3) | N2—C9—C13—C12 | −178.71 (18) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···N3 | 0.86 | 1.94 | 2.657 (2) | 140 |
N2—H2A···S1i | 0.86 | 2.60 | 3.4478 (19) | 169 |
C5—H5···O1ii | 0.93 | 2.47 | 3.289 (3) | 146 |
Symmetry codes: (i) −x+1, −y, −z; (ii) −x+3/2, y+1/2, −z+1/2. |
Subscribe to Acta Crystallographica Section E: Crystallographic Communications
The full text of this article is available to subscribers to the journal.
- Information on subscribing
- Sample issue
- If you have already subscribed, you may need to register