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The mol­ecule of the title compound, C13H11N3OS, is non-planar; the dihedral angles between the thio­urea and pyridine planes and between the thio­urea and benzene planes are 41.28 (8) and 27.47 (8)°, respectively.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806027516/xu2058sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806027516/xu2058Isup2.hkl
Contains datablock I

CCDC reference: 609353

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.043
  • wR factor = 0.106
  • Data-to-parameter ratio = 13.9

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.96 PLAT230_ALERT_2_C Hirshfeld Test Diff for S1 - C6 .. 5.16 su
Alert level G PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 2 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 1 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: SMART (Bruker, 2003); cell refinement: SAINT (Bruker, 2003); 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.

N-Benzoyl-N'-(3-pyridyl)thiourea top
Crystal data top
C13H11N3OSZ = 2
Mr = 257.31F(000) = 268
Triclinic, P1Dx = 1.363 Mg m3
Hall symbol: -P 1Melting point = 431–432 K
a = 7.828 (2) ÅMo Kα radiation, λ = 0.71073 Å
b = 8.688 (2) ÅCell parameters from 1073 reflections
c = 10.892 (3) Åθ = 2.7–25.9°
α = 111.785 (3)°µ = 0.25 mm1
β = 92.152 (4)°T = 293 K
γ = 111.499 (4)°Prism, colorless
V = 627.0 (3) Å30.25 × 0.15 × 0.06 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer
2263 independent reflections
Radiation source: fine-focus sealed tube1879 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.013
φ and ω scansθmax = 25.5°, θmin = 2.7°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2002)
h = 99
Tmin = 0.930, Tmax = 0.985k = 1010
3239 measured reflectionsl = 1213
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)] = 0.043Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.106H-atom parameters constrained
S = 1.01 w = 1/[σ2(Fo2) + (0.0512P)2 + 0.1913P]
where P = (Fo2 + 2Fc2)/3
2263 reflections(Δ/σ)max < 0.001
163 parametersΔρmax = 0.19 e Å3
0 restraintsΔρmin = 0.21 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
N10.2590 (3)0.6065 (2)0.55261 (18)0.0428 (4)
N20.2778 (2)0.1699 (2)0.48517 (17)0.0407 (4)
H20.28280.14000.40120.049*
N30.2196 (2)0.1298 (2)0.42742 (16)0.0366 (4)
H3A0.20300.21560.45330.044*
O10.2515 (2)0.06185 (19)0.24359 (14)0.0490 (4)
S10.21945 (9)0.05640 (7)0.68254 (5)0.0509 (2)
C10.2307 (3)0.4316 (3)0.4978 (2)0.0409 (5)
H10.15470.35830.41250.049*
C20.3083 (3)0.3530 (2)0.5608 (2)0.0359 (5)
C30.4218 (3)0.4607 (3)0.6869 (2)0.0441 (5)
H30.47790.41330.73160.053*
C40.4499 (3)0.6410 (3)0.7450 (2)0.0468 (5)
H40.52410.71680.83060.056*
C50.3676 (3)0.7080 (3)0.6756 (2)0.0432 (5)
H50.38870.83000.71630.052*
C60.2424 (3)0.0377 (2)0.52733 (19)0.0354 (5)
C70.2204 (3)0.1735 (3)0.2923 (2)0.0366 (5)
C80.1799 (3)0.3661 (3)0.20554 (19)0.0349 (4)
C90.2538 (3)0.4019 (3)0.0896 (2)0.0454 (5)
H90.32850.30620.06990.055*
C100.2177 (4)0.5779 (3)0.0031 (2)0.0551 (6)
H100.27040.60040.07330.066*
C110.1031 (4)0.7206 (3)0.0302 (2)0.0550 (6)
H110.07750.83950.02850.066*
C120.0267 (3)0.6870 (3)0.1439 (2)0.0521 (6)
H120.05110.78340.16170.062*
C130.0654 (3)0.5103 (3)0.2319 (2)0.0428 (5)
H130.01440.48820.30900.051*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0534 (11)0.0307 (9)0.0474 (11)0.0190 (8)0.0105 (9)0.0176 (8)
N20.0616 (12)0.0305 (9)0.0333 (9)0.0221 (8)0.0140 (8)0.0132 (7)
N30.0537 (11)0.0266 (8)0.0312 (9)0.0190 (8)0.0095 (8)0.0109 (7)
O10.0738 (11)0.0353 (8)0.0368 (8)0.0197 (8)0.0124 (7)0.0162 (7)
S10.0845 (5)0.0367 (3)0.0361 (3)0.0293 (3)0.0207 (3)0.0146 (2)
C10.0513 (13)0.0317 (11)0.0372 (11)0.0155 (9)0.0071 (9)0.0136 (9)
C20.0420 (11)0.0278 (10)0.0393 (11)0.0152 (9)0.0134 (9)0.0141 (9)
C30.0481 (13)0.0381 (12)0.0466 (13)0.0197 (10)0.0048 (10)0.0166 (10)
C40.0505 (13)0.0342 (11)0.0436 (12)0.0147 (10)0.0006 (10)0.0070 (9)
C50.0476 (13)0.0269 (10)0.0521 (13)0.0147 (9)0.0111 (10)0.0136 (10)
C60.0384 (11)0.0288 (10)0.0375 (11)0.0151 (9)0.0072 (9)0.0109 (9)
C70.0410 (11)0.0329 (11)0.0366 (11)0.0164 (9)0.0083 (9)0.0135 (9)
C80.0400 (11)0.0331 (10)0.0305 (10)0.0173 (9)0.0038 (8)0.0099 (8)
C90.0567 (14)0.0402 (12)0.0363 (11)0.0184 (10)0.0118 (10)0.0139 (9)
C100.0724 (17)0.0549 (15)0.0342 (12)0.0322 (13)0.0127 (11)0.0084 (11)
C110.0806 (18)0.0368 (12)0.0397 (13)0.0293 (12)0.0035 (12)0.0032 (10)
C120.0673 (16)0.0329 (12)0.0463 (13)0.0149 (11)0.0038 (12)0.0125 (10)
C130.0532 (13)0.0372 (12)0.0350 (11)0.0169 (10)0.0103 (10)0.0132 (9)
Geometric parameters (Å, º) top
N1—C51.335 (3)C4—C51.374 (3)
N1—C11.336 (3)C4—H40.9300
N2—C61.332 (2)C5—H50.9300
N2—C21.415 (2)C7—C81.486 (3)
N2—H20.8600C8—C131.385 (3)
N3—C71.378 (2)C8—C91.386 (3)
N3—C61.398 (2)C9—C101.378 (3)
N3—H3A0.8600C9—H90.9300
O1—C71.224 (2)C10—C111.380 (3)
S1—C61.660 (2)C10—H100.9300
C1—C21.387 (3)C11—C121.376 (3)
C1—H10.9300C11—H110.9300
C2—C31.377 (3)C12—C131.383 (3)
C3—C41.380 (3)C12—H120.9300
C3—H30.9300C13—H130.9300
C5—N1—C1116.68 (18)N2—C6—S1125.80 (15)
C6—N2—C2128.35 (17)N3—C6—S1119.62 (14)
C6—N2—H2115.8O1—C7—N3122.82 (18)
C2—N2—H2115.8O1—C7—C8120.53 (18)
C7—N3—C6127.54 (16)N3—C7—C8116.65 (16)
C7—N3—H3A116.2C13—C8—C9118.98 (18)
C6—N3—H3A116.2C13—C8—C7123.14 (18)
N1—C1—C2123.8 (2)C9—C8—C7117.80 (18)
N1—C1—H1118.1C10—C9—C8120.7 (2)
C2—C1—H1118.1C10—C9—H9119.6
C3—C2—C1118.53 (18)C8—C9—H9119.6
C3—C2—N2124.16 (18)C11—C10—C9119.8 (2)
C1—C2—N2117.07 (18)C11—C10—H10120.1
C2—C3—C4118.04 (19)C9—C10—H10120.1
C2—C3—H3121.0C12—C11—C10120.1 (2)
C4—C3—H3121.0C12—C11—H11120.0
C5—C4—C3119.7 (2)C10—C11—H11120.0
C5—C4—H4120.2C11—C12—C13120.1 (2)
C3—C4—H4120.2C11—C12—H12119.9
N1—C5—C4123.22 (19)C13—C12—H12119.9
N1—C5—H5118.4C8—C13—C12120.3 (2)
C4—C5—H5118.4C8—C13—H13119.9
N2—C6—N3114.56 (17)C12—C13—H13119.9
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2···O10.861.872.597 (2)141
N3—H3A···N1i0.862.343.164 (3)162
Symmetry code: (i) x, y1, z.
 

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