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The title compound, C13H12N2OS, was prepared by the reaction of (4-pyrid­yl)methanol with phenyl isothio­cyanate and NaOH in a 1,4-dioxane solution. The asymmetric unit contains two independent mol­ecules. The mol­ecular structure and packing are stabilized by N—H...N inter­molecular hydrogen-bond inter­actions and C—H...π inter­actions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680602191X/rz2044sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680602191X/rz2044Isup2.hkl
Contains datablock I

CCDC reference: 614880

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.049
  • wR factor = 0.130
  • Data-to-parameter ratio = 17.3

checkCIF/PLATON results

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Alert level C PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low .... 45 Perc. PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.98 PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature . 293 K PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.01 PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5 PLAT480_ALERT_4_C Long H...A H-Bond Reported H23A .. CG2 .. 3.08 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H26A .. CG3 .. 2.96 Ang.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 8 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 3 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software; data reduction: NRCVAX (Gabe et al., 1989); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Sheldrick, 1990); software used to prepare material for publication: WinGX (Farrugia, 1999).

(4-Pyridyl)methyl N-phenylthiocarbamate top
Crystal data top
C13H12N2OSF(000) = 1024
Mr = 244.32Dx = 1.303 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -p 2y bcCell parameters from 25 reflections
a = 9.4370 (19) Åθ = 4–14°
b = 16.714 (3) ŵ = 0.24 mm1
c = 17.907 (5) ÅT = 293 K
β = 118.16 (2)°Block, colourless
V = 2490.1 (10) Å30.25 × 0.20 × 0.18 mm
Z = 8
Data collection top
Enraf–Nonius CAD-4
diffractometer
Rint = 0.040
Radiation source: fine-focus sealed tubeθmax = 27.0°, θmin = 1.8°
Graphite monochromatorh = 1212
ω scansk = 2121
5620 measured reflectionsl = 2222
5311 independent reflections3 standard reflections every 100 reflections
2381 reflections with I > 2σ(I) intensity decay: none
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)] = 0.049Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.130H-atom parameters constrained
S = 1.00 w = 1/[σ2(Fo2) + (0.0477P)2]
where P = (Fo2 + 2Fc2)/3
5311 reflections(Δ/σ)max < 0.001
307 parametersΔρmax = 0.21 e Å3
0 restraintsΔρmin = 0.25 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
S10.92123 (11)0.45202 (4)0.36479 (6)0.0622 (3)
O10.8894 (2)0.29697 (10)0.38314 (13)0.0481 (5)
N10.6980 (3)0.36754 (12)0.38481 (14)0.0418 (6)
H1A0.66800.31970.38820.050*
N21.0746 (3)0.02747 (14)0.3912 (2)0.0601 (8)
C10.6470 (4)0.50627 (17)0.41482 (19)0.0494 (8)
H1B0.75370.52100.43400.059*
C20.5366 (4)0.56124 (18)0.4139 (2)0.0606 (9)
H2B0.56990.61330.43190.073*
C30.3797 (4)0.5407 (2)0.3870 (2)0.0661 (10)
H3A0.30680.57870.38600.079*
C40.3303 (4)0.4636 (2)0.3615 (2)0.0653 (10)
H4A0.22430.44880.34420.078*
C50.4391 (4)0.40791 (18)0.3617 (2)0.0520 (8)
H5A0.40560.35560.34480.062*
C60.5965 (3)0.42884 (16)0.38670 (18)0.0400 (7)
C70.8336 (3)0.37267 (15)0.37862 (17)0.0381 (7)
C81.0307 (4)0.28289 (17)0.3746 (2)0.0551 (9)
H8A1.12310.30950.41940.066*
H8B1.01630.30220.32040.066*
C91.0525 (3)0.19408 (17)0.3808 (2)0.0422 (7)
C101.0864 (4)0.15395 (19)0.4545 (2)0.0575 (9)
H10A1.10240.18260.50230.069*
C111.0966 (4)0.07195 (19)0.4578 (2)0.0592 (9)
H11A1.11980.04640.50850.071*
C121.0437 (4)0.0664 (2)0.3205 (2)0.0670 (10)
H12A1.02990.03670.27370.080*
C131.0309 (4)0.14906 (19)0.3125 (2)0.0572 (9)
H13A1.00790.17350.26130.069*
S20.62607 (11)0.27865 (4)0.15162 (6)0.0632 (3)
O20.6454 (2)0.43374 (10)0.12512 (13)0.0496 (6)
N30.8317 (3)0.36345 (12)0.11833 (15)0.0446 (6)
H3B0.85190.40990.10490.054*
N40.4171 (3)0.70050 (14)0.12728 (17)0.0524 (7)
C140.8887 (4)0.22698 (16)0.08750 (19)0.0481 (8)
H14A0.77960.21570.05670.058*
C151.0014 (5)0.16938 (18)0.0966 (2)0.0587 (9)
H15A0.96770.11910.07250.070*
C161.1635 (5)0.1864 (2)0.1414 (2)0.0657 (10)
H16A1.23870.14720.14860.079*
C171.2135 (4)0.2611 (2)0.1751 (2)0.0640 (10)
H17A1.32260.27300.20350.077*
C181.1021 (4)0.31846 (18)0.16705 (19)0.0504 (8)
H18A1.13640.36900.19040.060*
C190.9391 (4)0.30112 (16)0.12428 (18)0.0403 (7)
C200.7037 (3)0.35888 (16)0.13104 (18)0.0404 (7)
C210.5210 (4)0.44800 (17)0.1481 (2)0.0510 (8)
H21A0.55600.43090.20590.061*
H21B0.42510.41820.11100.061*
C220.4860 (3)0.53610 (17)0.13958 (18)0.0415 (7)
C230.5312 (4)0.58712 (18)0.09403 (19)0.0522 (8)
H23A0.58650.56750.06650.063*
C240.4940 (4)0.66768 (17)0.0895 (2)0.0559 (9)
H24A0.52500.70070.05800.067*
C250.3719 (4)0.65086 (19)0.1706 (2)0.0585 (9)
H25A0.31490.67200.19660.070*
C260.4049 (4)0.56986 (17)0.1790 (2)0.0543 (9)
H26A0.37280.53820.21100.065*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0706 (6)0.0318 (4)0.1095 (8)0.0060 (4)0.0633 (6)0.0005 (5)
O10.0518 (13)0.0287 (11)0.0779 (16)0.0039 (9)0.0423 (12)0.0040 (10)
N10.0425 (15)0.0284 (13)0.0609 (17)0.0007 (11)0.0296 (14)0.0037 (11)
N20.0618 (19)0.0334 (15)0.087 (2)0.0035 (13)0.0367 (18)0.0011 (16)
C10.0502 (19)0.0373 (17)0.066 (2)0.0005 (15)0.0313 (18)0.0027 (16)
C20.079 (3)0.0404 (19)0.077 (3)0.0084 (18)0.048 (2)0.0011 (17)
C30.067 (3)0.067 (2)0.080 (3)0.023 (2)0.048 (2)0.005 (2)
C40.050 (2)0.069 (3)0.086 (3)0.0033 (19)0.040 (2)0.002 (2)
C50.049 (2)0.0468 (19)0.067 (2)0.0023 (16)0.0327 (19)0.0042 (17)
C60.0423 (18)0.0384 (17)0.0448 (19)0.0046 (14)0.0251 (16)0.0033 (14)
C70.0435 (18)0.0319 (16)0.0449 (19)0.0004 (13)0.0258 (16)0.0029 (13)
C80.058 (2)0.0369 (18)0.086 (3)0.0073 (15)0.047 (2)0.0038 (16)
C90.0421 (18)0.0350 (16)0.057 (2)0.0042 (13)0.0292 (17)0.0025 (16)
C100.079 (2)0.0452 (19)0.057 (2)0.0017 (18)0.039 (2)0.0033 (17)
C110.068 (2)0.048 (2)0.065 (3)0.0092 (17)0.035 (2)0.0144 (18)
C120.087 (3)0.052 (2)0.066 (3)0.0089 (19)0.039 (2)0.0160 (19)
C130.073 (2)0.051 (2)0.052 (2)0.0125 (18)0.032 (2)0.0046 (17)
S20.0778 (6)0.0340 (4)0.0991 (8)0.0020 (4)0.0593 (6)0.0084 (5)
O20.0576 (13)0.0299 (11)0.0766 (16)0.0095 (9)0.0442 (13)0.0039 (10)
N30.0540 (16)0.0231 (12)0.0646 (18)0.0040 (11)0.0344 (15)0.0036 (11)
N40.0536 (17)0.0377 (15)0.0720 (19)0.0088 (12)0.0345 (16)0.0041 (14)
C140.061 (2)0.0343 (17)0.048 (2)0.0070 (15)0.0241 (17)0.0007 (15)
C150.085 (3)0.0423 (19)0.052 (2)0.0197 (19)0.035 (2)0.0005 (16)
C160.076 (3)0.064 (2)0.065 (3)0.037 (2)0.040 (2)0.0085 (19)
C170.056 (2)0.073 (3)0.067 (3)0.0151 (19)0.032 (2)0.002 (2)
C180.053 (2)0.0454 (19)0.057 (2)0.0035 (16)0.0296 (18)0.0038 (16)
C190.051 (2)0.0320 (16)0.0466 (19)0.0093 (14)0.0301 (17)0.0054 (14)
C200.0459 (19)0.0277 (15)0.0465 (19)0.0056 (13)0.0208 (16)0.0012 (13)
C210.053 (2)0.0390 (18)0.071 (2)0.0089 (15)0.0378 (19)0.0038 (16)
C220.0389 (17)0.0346 (17)0.048 (2)0.0070 (13)0.0183 (16)0.0008 (14)
C230.061 (2)0.0471 (19)0.057 (2)0.0159 (16)0.0345 (19)0.0025 (16)
C240.064 (2)0.0401 (19)0.069 (2)0.0109 (16)0.036 (2)0.0083 (17)
C250.064 (2)0.0468 (19)0.077 (3)0.0113 (17)0.044 (2)0.0046 (18)
C260.062 (2)0.0464 (19)0.069 (2)0.0129 (16)0.043 (2)0.0065 (17)
Geometric parameters (Å, º) top
S1—C71.642 (3)S2—C201.651 (3)
O1—C71.358 (3)O2—C201.351 (3)
O1—C81.432 (3)O2—C211.435 (3)
N1—C71.339 (3)N3—C201.333 (3)
N1—C61.414 (3)N3—C191.422 (3)
N1—H1A0.8600N3—H3B0.8600
N2—C121.328 (4)N4—C241.322 (4)
N2—C111.336 (4)N4—C251.336 (4)
C1—C21.383 (4)C14—C191.378 (4)
C1—C61.389 (4)C14—C151.386 (4)
C1—H1B0.9300C14—H14A0.9300
C2—C31.368 (4)C15—C161.381 (5)
C2—H2B0.9300C15—H15A0.9300
C3—C41.373 (4)C16—C171.369 (4)
C3—H3A0.9300C16—H16A0.9300
C4—C51.384 (4)C17—C181.380 (4)
C4—H4A0.9300C17—H17A0.9300
C5—C61.379 (4)C18—C191.387 (4)
C5—H5A0.9300C18—H18A0.9300
C8—C91.495 (4)C21—C221.501 (4)
C8—H8A0.9700C21—H21A0.9700
C8—H8B0.9700C21—H21B0.9700
C9—C131.366 (4)C22—C231.380 (4)
C9—C101.377 (4)C22—C261.383 (4)
C10—C111.373 (4)C23—C241.384 (4)
C10—H10A0.9300C23—H23A0.9300
C11—H11A0.9300C24—H24A0.9300
C12—C131.388 (4)C25—C261.382 (4)
C12—H12A0.9300C25—H25A0.9300
C13—H13A0.9300C26—H26A0.9300
C7—O1—C8120.1 (2)C20—O2—C21119.3 (2)
C7—N1—C6129.8 (2)C20—N3—C19128.1 (2)
C7—N1—H1A115.1C20—N3—H3B116.0
C6—N1—H1A115.1C19—N3—H3B116.0
C12—N2—C11116.8 (3)C24—N4—C25116.3 (3)
C2—C1—C6119.1 (3)C19—C14—C15119.7 (3)
C2—C1—H1B120.4C19—C14—H14A120.1
C6—C1—H1B120.4C15—C14—H14A120.1
C3—C2—C1121.5 (3)C16—C15—C14120.2 (3)
C3—C2—H2B119.3C16—C15—H15A119.9
C1—C2—H2B119.3C14—C15—H15A119.9
C2—C3—C4119.6 (3)C17—C16—C15120.1 (3)
C2—C3—H3A120.2C17—C16—H16A120.0
C4—C3—H3A120.2C15—C16—H16A120.0
C3—C4—C5119.7 (3)C16—C17—C18120.0 (3)
C3—C4—H4A120.2C16—C17—H17A120.0
C5—C4—H4A120.2C18—C17—H17A120.0
C6—C5—C4121.0 (3)C17—C18—C19120.3 (3)
C6—C5—H5A119.5C17—C18—H18A119.9
C4—C5—H5A119.5C19—C18—H18A119.9
C5—C6—C1119.1 (3)C14—C19—C18119.6 (3)
C5—C6—N1116.5 (3)C14—C19—N3123.4 (3)
C1—C6—N1124.3 (3)C18—C19—N3117.0 (3)
N1—C7—O1107.1 (2)N3—C20—O2107.6 (2)
N1—C7—S1129.3 (2)N3—C20—S2128.2 (2)
O1—C7—S1123.6 (2)O2—C20—S2124.3 (2)
O1—C8—C9104.9 (2)O2—C21—C22107.7 (2)
O1—C8—H8A110.8O2—C21—H21A110.2
C9—C8—H8A110.8C22—C21—H21A110.2
O1—C8—H8B110.8O2—C21—H21B110.2
C9—C8—H8B110.8C22—C21—H21B110.2
H8A—C8—H8B108.8H21A—C21—H21B108.5
C13—C9—C10117.3 (3)C23—C22—C26116.7 (3)
C13—C9—C8121.5 (3)C23—C22—C21123.5 (3)
C10—C9—C8121.1 (3)C26—C22—C21119.8 (3)
C11—C10—C9120.5 (3)C22—C23—C24119.7 (3)
C11—C10—H10A119.7C22—C23—H23A120.2
C9—C10—H10A119.7C24—C23—H23A120.2
N2—C11—C10122.5 (3)N4—C24—C23124.0 (3)
N2—C11—H11A118.7N4—C24—H24A118.0
C10—C11—H11A118.7C23—C24—H24A118.0
N2—C12—C13123.8 (3)N4—C25—C26123.6 (3)
N2—C12—H12A118.1N4—C25—H25A118.2
C13—C12—H12A118.1C26—C25—H25A118.2
C9—C13—C12119.1 (3)C25—C26—C22119.7 (3)
C9—C13—H13A120.4C25—C26—H26A120.2
C12—C13—H13A120.4C22—C26—H26A120.2
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···N4i0.862.122.966 (3)170
N3—H3B···N2ii0.862.072.910 (3)164
C10—H10A···Cg1iii0.932.863.757 (2)162
C13—H13A···Cg10.932.803.686 (1)161
C23—H23A···Cg2ii0.933.083.685 (2)125
C26—H26A···Cg30.932.963.718 (2)140
Symmetry codes: (i) x+1, y1/2, z+1/2; (ii) x+2, y+1/2, z+1/2; (iii) x, y+1/2, z+1/2.
 

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