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In the title compound, C14H13N3OS, the dihedral angle between the two aromatic ring planes is 34.00 (8)°. The crystal packing shows centrosymmetric dimers formed by inter­molecular N—H...S hydrogen bonds which are stacked along [010].

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806032302/ga2001sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806032302/ga2001Isup2.hkl
Contains datablock I

CCDC reference: 621313

Key indicators

  • Single-crystal X-ray study
  • T = 120 K
  • Mean [sigma](C-C)= 0.003 Å
  • R factor = 0.050
  • wR factor = 0.112
  • Data-to-parameter ratio = 18.8

checkCIF/PLATON results

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No errors found in this datablock

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Bruker, 2002); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

1-Benzoyl-3-(4-methylpyridin-2-yl)thiourea top
Crystal data top
C14H13N3OSF(000) = 568
Mr = 271.33Dx = 1.356 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 1567 reflections
a = 11.9247 (15) Åθ = 2.4–25.0°
b = 5.1952 (7) ŵ = 0.24 mm1
c = 21.615 (3) ÅT = 120 K
β = 96.962 (3)°Needle, pale yellow
V = 1329.2 (3) Å30.48 × 0.18 × 0.12 mm
Z = 4
Data collection top
Bruker SMART APEX
diffractometer
3254 independent reflections
Radiation source: sealed tube2026 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.062
φ and ω scansθmax = 28.2°, θmin = 1.7°
Absorption correction: multi-scan
(SADABS; Bruker, 2002)
h = 1515
Tmin = 0.912, Tmax = 0.971k = 66
11451 measured reflectionsl = 2828
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)] = 0.050Hydrogen site location: difference Fourier map
wR(F2) = 0.112H-atom parameters constrained
S = 0.88 w = 1/[σ2(Fo2) + (0.044P)2]
where P = (Fo2 + 2Fc2)/3
3254 reflections(Δ/σ)max < 0.001
173 parametersΔρmax = 0.38 e Å3
0 restraintsΔρmin = 0.31 e Å3
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
S10.02463 (4)0.69073 (13)0.08562 (2)0.03769 (19)
O10.37889 (11)0.4364 (3)0.05884 (7)0.0405 (4)
N10.36791 (13)0.9156 (3)0.19281 (8)0.0344 (4)
N20.24871 (13)0.7134 (3)0.12008 (7)0.0291 (4)
H2B0.31350.64690.11250.035*
N30.18649 (12)0.4287 (3)0.04268 (7)0.0278 (4)
H3A0.12880.35110.02120.033*
C10.39131 (18)1.0899 (5)0.23789 (10)0.0404 (6)
H1A0.46701.10230.25730.048*
C20.31223 (18)1.2523 (4)0.25788 (10)0.0394 (6)
H2A0.33361.37360.29000.047*
C30.20114 (17)1.2376 (4)0.23071 (9)0.0321 (5)
C40.17485 (16)1.0588 (4)0.18362 (9)0.0292 (5)
H4A0.10001.04420.16320.035*
C50.26024 (16)0.9021 (4)0.16702 (8)0.0278 (5)
C60.11200 (18)1.4089 (5)0.25197 (10)0.0411 (6)
H6A0.08971.34300.29120.062*
H6B0.04601.41200.22020.062*
H6C0.14201.58370.25840.062*
C70.15969 (15)0.6142 (4)0.08464 (8)0.0276 (5)
C80.29257 (16)0.3499 (4)0.03026 (9)0.0290 (5)
C90.29646 (15)0.1549 (4)0.01933 (8)0.0272 (5)
C100.20970 (17)0.0189 (4)0.03680 (9)0.0313 (5)
H10A0.14190.01110.01790.038*
C110.22211 (19)0.2024 (4)0.08146 (10)0.0382 (5)
H11A0.16240.31970.09370.046*
C120.3210 (2)0.2163 (4)0.10846 (10)0.0400 (6)
H12A0.32960.34510.13870.048*
C130.40745 (18)0.0440 (4)0.09172 (9)0.0370 (5)
H13A0.47500.05310.11080.044*
C140.39563 (16)0.1413 (4)0.04727 (9)0.0320 (5)
H14A0.45520.25980.03570.038*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0223 (3)0.0564 (4)0.0340 (3)0.0002 (2)0.0023 (2)0.0133 (3)
O10.0263 (7)0.0465 (10)0.0468 (9)0.0034 (7)0.0028 (7)0.0139 (8)
N10.0294 (9)0.0377 (11)0.0348 (9)0.0021 (8)0.0020 (7)0.0035 (9)
N20.0224 (8)0.0332 (11)0.0310 (9)0.0014 (7)0.0006 (7)0.0059 (8)
N30.0215 (8)0.0337 (10)0.0276 (8)0.0034 (7)0.0001 (7)0.0047 (8)
C10.0354 (12)0.0448 (15)0.0384 (12)0.0065 (11)0.0061 (10)0.0063 (11)
C20.0461 (13)0.0373 (14)0.0333 (12)0.0060 (11)0.0007 (10)0.0068 (10)
C30.0408 (12)0.0283 (12)0.0283 (11)0.0038 (9)0.0082 (9)0.0043 (9)
C40.0285 (10)0.0296 (12)0.0293 (10)0.0019 (9)0.0031 (8)0.0015 (9)
C50.0292 (10)0.0289 (12)0.0251 (10)0.0041 (9)0.0020 (8)0.0025 (9)
C60.0469 (13)0.0365 (14)0.0415 (12)0.0004 (11)0.0121 (10)0.0072 (11)
C70.0285 (10)0.0301 (12)0.0238 (10)0.0004 (9)0.0016 (8)0.0010 (9)
C80.0270 (10)0.0280 (12)0.0318 (10)0.0020 (9)0.0026 (8)0.0042 (9)
C90.0279 (10)0.0262 (12)0.0267 (10)0.0045 (9)0.0009 (8)0.0035 (9)
C100.0363 (11)0.0270 (12)0.0308 (11)0.0012 (9)0.0048 (9)0.0050 (10)
C110.0491 (13)0.0285 (13)0.0359 (12)0.0039 (10)0.0011 (10)0.0018 (10)
C120.0571 (14)0.0332 (14)0.0292 (11)0.0099 (11)0.0033 (10)0.0018 (10)
C130.0385 (12)0.0403 (14)0.0323 (11)0.0107 (11)0.0057 (9)0.0048 (11)
C140.0305 (10)0.0326 (13)0.0322 (11)0.0046 (9)0.0012 (9)0.0033 (10)
Geometric parameters (Å, º) top
S1—C71.6616 (19)C4—H4A0.9500
O1—C81.220 (2)C6—H6A0.9800
N1—C11.334 (3)C6—H6B0.9800
N1—C51.338 (2)C6—H6C0.9800
N2—C71.335 (2)C8—C91.480 (3)
N2—C51.406 (2)C9—C101.391 (3)
N2—H2B0.8800C9—C141.393 (3)
N3—C81.386 (2)C10—C111.377 (3)
N3—C71.387 (2)C10—H10A0.9500
N3—H3A0.8800C11—C121.380 (3)
C1—C21.374 (3)C11—H11A0.9500
C1—H1A0.9500C12—C131.380 (3)
C2—C31.385 (3)C12—H12A0.9500
C2—H2A0.9500C13—C141.379 (3)
C3—C41.385 (3)C13—H13A0.9500
C3—C61.501 (3)C14—H14A0.9500
C4—C51.385 (3)
C1—N1—C5116.43 (18)H6A—C6—H6C109.5
C7—N2—C5133.23 (17)H6B—C6—H6C109.5
C7—N2—H2B113.4N2—C7—N3114.41 (16)
C5—N2—H2B113.4N2—C7—S1127.22 (16)
C8—N3—C7128.30 (16)N3—C7—S1118.37 (13)
C8—N3—H3A115.9O1—C8—N3121.78 (19)
C7—N3—H3A115.9O1—C8—C9121.35 (17)
N1—C1—C2123.76 (19)N3—C8—C9116.87 (16)
N1—C1—H1A118.1C10—C9—C14119.47 (19)
C2—C1—H1A118.1C10—C9—C8123.63 (18)
C1—C2—C3119.4 (2)C14—C9—C8116.84 (18)
C1—C2—H2A120.3C11—C10—C9120.0 (2)
C3—C2—H2A120.3C11—C10—H10A120.0
C2—C3—C4117.93 (19)C9—C10—H10A120.0
C2—C3—C6120.94 (19)C10—C11—C12120.2 (2)
C4—C3—C6121.13 (18)C10—C11—H11A119.9
C5—C4—C3118.47 (18)C12—C11—H11A119.9
C5—C4—H4A120.8C11—C12—C13120.3 (2)
C3—C4—H4A120.8C11—C12—H12A119.8
N1—C5—C4124.02 (18)C13—C12—H12A119.8
N1—C5—N2110.03 (17)C14—C13—C12119.9 (2)
C4—C5—N2125.92 (17)C14—C13—H13A120.0
C3—C6—H6A109.5C12—C13—H13A120.0
C3—C6—H6B109.5C13—C14—C9120.1 (2)
H6A—C6—H6B109.5C13—C14—H14A120.0
C3—C6—H6C109.5C9—C14—H14A120.0
C5—N1—C1—C20.6 (3)C8—N3—C7—S1174.38 (16)
N1—C1—C2—C30.3 (3)C7—N3—C8—O12.9 (3)
C1—C2—C3—C40.6 (3)C7—N3—C8—C9177.27 (17)
C1—C2—C3—C6179.0 (2)O1—C8—C9—C10154.7 (2)
C2—C3—C4—C51.1 (3)N3—C8—C9—C1025.2 (3)
C6—C3—C4—C5178.53 (19)O1—C8—C9—C1422.3 (3)
C1—N1—C5—C41.2 (3)N3—C8—C9—C14157.83 (17)
C1—N1—C5—N2179.31 (18)C14—C9—C10—C110.1 (3)
C3—C4—C5—N11.5 (3)C8—C9—C10—C11176.99 (18)
C3—C4—C5—N2179.29 (18)C9—C10—C11—C120.7 (3)
C7—N2—C5—N1174.1 (2)C10—C11—C12—C131.1 (3)
C7—N2—C5—C47.9 (3)C11—C12—C13—C140.7 (3)
C5—N2—C7—N3179.47 (18)C12—C13—C14—C90.1 (3)
C5—N2—C7—S10.0 (3)C10—C9—C14—C130.2 (3)
C8—N3—C7—N25.2 (3)C8—C9—C14—C13176.87 (17)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2B···O10.881.832.594 (2)143
N3—H3A···S1i0.882.773.567 (2)150
Symmetry code: (i) x, y+1, z.
 

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