The title compound, C
13H
12N
2OS, 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
CCDC reference: 614880
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.005 Å
- R factor = 0.049
- wR factor = 0.130
- Data-to-parameter ratio = 17.3
checkCIF/PLATON results
No syntax errors found
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
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
C13H12N2OS | F(000) = 1024 |
Mr = 244.32 | Dx = 1.303 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -p 2y bc | Cell parameters from 25 reflections |
a = 9.4370 (19) Å | θ = 4–14° |
b = 16.714 (3) Å | µ = 0.24 mm−1 |
c = 17.907 (5) Å | T = 293 K |
β = 118.16 (2)° | Block, colourless |
V = 2490.1 (10) Å3 | 0.25 × 0.20 × 0.18 mm |
Z = 8 | |
Data collection top
Enraf–Nonius CAD-4 diffractometer | Rint = 0.040 |
Radiation source: fine-focus sealed tube | θmax = 27.0°, θmin = 1.8° |
Graphite monochromator | h = −12→12 |
ω scans | k = −21→21 |
5620 measured reflections | l = −22→22 |
5311 independent reflections | 3 standard reflections every 100 reflections |
2381 reflections with I > 2σ(I) | intensity decay: none |
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)] = 0.049 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.130 | H-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 parameters | Δρmax = 0.21 e Å−3 |
0 restraints | Δρmin = −0.25 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
S1 | 0.92123 (11) | 0.45202 (4) | 0.36479 (6) | 0.0622 (3) | |
O1 | 0.8894 (2) | 0.29697 (10) | 0.38314 (13) | 0.0481 (5) | |
N1 | 0.6980 (3) | 0.36754 (12) | 0.38481 (14) | 0.0418 (6) | |
H1A | 0.6680 | 0.3197 | 0.3882 | 0.050* | |
N2 | 1.0746 (3) | 0.02747 (14) | 0.3912 (2) | 0.0601 (8) | |
C1 | 0.6470 (4) | 0.50627 (17) | 0.41482 (19) | 0.0494 (8) | |
H1B | 0.7537 | 0.5210 | 0.4340 | 0.059* | |
C2 | 0.5366 (4) | 0.56124 (18) | 0.4139 (2) | 0.0606 (9) | |
H2B | 0.5699 | 0.6133 | 0.4319 | 0.073* | |
C3 | 0.3797 (4) | 0.5407 (2) | 0.3870 (2) | 0.0661 (10) | |
H3A | 0.3068 | 0.5787 | 0.3860 | 0.079* | |
C4 | 0.3303 (4) | 0.4636 (2) | 0.3615 (2) | 0.0653 (10) | |
H4A | 0.2243 | 0.4488 | 0.3442 | 0.078* | |
C5 | 0.4391 (4) | 0.40791 (18) | 0.3617 (2) | 0.0520 (8) | |
H5A | 0.4056 | 0.3556 | 0.3448 | 0.062* | |
C6 | 0.5965 (3) | 0.42884 (16) | 0.38670 (18) | 0.0400 (7) | |
C7 | 0.8336 (3) | 0.37267 (15) | 0.37862 (17) | 0.0381 (7) | |
C8 | 1.0307 (4) | 0.28289 (17) | 0.3746 (2) | 0.0551 (9) | |
H8A | 1.1231 | 0.3095 | 0.4194 | 0.066* | |
H8B | 1.0163 | 0.3022 | 0.3204 | 0.066* | |
C9 | 1.0525 (3) | 0.19408 (17) | 0.3808 (2) | 0.0422 (7) | |
C10 | 1.0864 (4) | 0.15395 (19) | 0.4545 (2) | 0.0575 (9) | |
H10A | 1.1024 | 0.1826 | 0.5023 | 0.069* | |
C11 | 1.0966 (4) | 0.07195 (19) | 0.4578 (2) | 0.0592 (9) | |
H11A | 1.1198 | 0.0464 | 0.5085 | 0.071* | |
C12 | 1.0437 (4) | 0.0664 (2) | 0.3205 (2) | 0.0670 (10) | |
H12A | 1.0299 | 0.0367 | 0.2737 | 0.080* | |
C13 | 1.0309 (4) | 0.14906 (19) | 0.3125 (2) | 0.0572 (9) | |
H13A | 1.0079 | 0.1735 | 0.2613 | 0.069* | |
S2 | 0.62607 (11) | 0.27865 (4) | 0.15162 (6) | 0.0632 (3) | |
O2 | 0.6454 (2) | 0.43374 (10) | 0.12512 (13) | 0.0496 (6) | |
N3 | 0.8317 (3) | 0.36345 (12) | 0.11833 (15) | 0.0446 (6) | |
H3B | 0.8519 | 0.4099 | 0.1049 | 0.054* | |
N4 | 0.4171 (3) | 0.70050 (14) | 0.12728 (17) | 0.0524 (7) | |
C14 | 0.8887 (4) | 0.22698 (16) | 0.08750 (19) | 0.0481 (8) | |
H14A | 0.7796 | 0.2157 | 0.0567 | 0.058* | |
C15 | 1.0014 (5) | 0.16938 (18) | 0.0966 (2) | 0.0587 (9) | |
H15A | 0.9677 | 0.1191 | 0.0725 | 0.070* | |
C16 | 1.1635 (5) | 0.1864 (2) | 0.1414 (2) | 0.0657 (10) | |
H16A | 1.2387 | 0.1472 | 0.1486 | 0.079* | |
C17 | 1.2135 (4) | 0.2611 (2) | 0.1751 (2) | 0.0640 (10) | |
H17A | 1.3226 | 0.2730 | 0.2035 | 0.077* | |
C18 | 1.1021 (4) | 0.31846 (18) | 0.16705 (19) | 0.0504 (8) | |
H18A | 1.1364 | 0.3690 | 0.1904 | 0.060* | |
C19 | 0.9391 (4) | 0.30112 (16) | 0.12428 (18) | 0.0403 (7) | |
C20 | 0.7037 (3) | 0.35888 (16) | 0.13104 (18) | 0.0404 (7) | |
C21 | 0.5210 (4) | 0.44800 (17) | 0.1481 (2) | 0.0510 (8) | |
H21A | 0.5560 | 0.4309 | 0.2059 | 0.061* | |
H21B | 0.4251 | 0.4182 | 0.1110 | 0.061* | |
C22 | 0.4860 (3) | 0.53610 (17) | 0.13958 (18) | 0.0415 (7) | |
C23 | 0.5312 (4) | 0.58712 (18) | 0.09403 (19) | 0.0522 (8) | |
H23A | 0.5865 | 0.5675 | 0.0665 | 0.063* | |
C24 | 0.4940 (4) | 0.66768 (17) | 0.0895 (2) | 0.0559 (9) | |
H24A | 0.5250 | 0.7007 | 0.0580 | 0.067* | |
C25 | 0.3719 (4) | 0.65086 (19) | 0.1706 (2) | 0.0585 (9) | |
H25A | 0.3149 | 0.6720 | 0.1966 | 0.070* | |
C26 | 0.4049 (4) | 0.56986 (17) | 0.1790 (2) | 0.0543 (9) | |
H26A | 0.3728 | 0.5382 | 0.2110 | 0.065* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S1 | 0.0706 (6) | 0.0318 (4) | 0.1095 (8) | −0.0060 (4) | 0.0633 (6) | −0.0005 (5) |
O1 | 0.0518 (13) | 0.0287 (11) | 0.0779 (16) | 0.0039 (9) | 0.0423 (12) | 0.0040 (10) |
N1 | 0.0425 (15) | 0.0284 (13) | 0.0609 (17) | −0.0007 (11) | 0.0296 (14) | 0.0037 (11) |
N2 | 0.0618 (19) | 0.0334 (15) | 0.087 (2) | 0.0035 (13) | 0.0367 (18) | 0.0011 (16) |
C1 | 0.0502 (19) | 0.0373 (17) | 0.066 (2) | −0.0005 (15) | 0.0313 (18) | −0.0027 (16) |
C2 | 0.079 (3) | 0.0404 (19) | 0.077 (3) | 0.0084 (18) | 0.048 (2) | −0.0011 (17) |
C3 | 0.067 (3) | 0.067 (2) | 0.080 (3) | 0.023 (2) | 0.048 (2) | 0.005 (2) |
C4 | 0.050 (2) | 0.069 (3) | 0.086 (3) | 0.0033 (19) | 0.040 (2) | −0.002 (2) |
C5 | 0.049 (2) | 0.0468 (19) | 0.067 (2) | −0.0023 (16) | 0.0327 (19) | −0.0042 (17) |
C6 | 0.0423 (18) | 0.0384 (17) | 0.0448 (19) | 0.0046 (14) | 0.0251 (16) | 0.0033 (14) |
C7 | 0.0435 (18) | 0.0319 (16) | 0.0449 (19) | −0.0004 (13) | 0.0258 (16) | −0.0029 (13) |
C8 | 0.058 (2) | 0.0369 (18) | 0.086 (3) | 0.0073 (15) | 0.047 (2) | 0.0038 (16) |
C9 | 0.0421 (18) | 0.0350 (16) | 0.057 (2) | 0.0042 (13) | 0.0292 (17) | 0.0025 (16) |
C10 | 0.079 (2) | 0.0452 (19) | 0.057 (2) | 0.0017 (18) | 0.039 (2) | −0.0033 (17) |
C11 | 0.068 (2) | 0.048 (2) | 0.065 (3) | 0.0092 (17) | 0.035 (2) | 0.0144 (18) |
C12 | 0.087 (3) | 0.052 (2) | 0.066 (3) | 0.0089 (19) | 0.039 (2) | −0.0160 (19) |
C13 | 0.073 (2) | 0.051 (2) | 0.052 (2) | 0.0125 (18) | 0.032 (2) | 0.0046 (17) |
S2 | 0.0778 (6) | 0.0340 (4) | 0.0991 (8) | 0.0020 (4) | 0.0593 (6) | 0.0084 (5) |
O2 | 0.0576 (13) | 0.0299 (11) | 0.0766 (16) | 0.0095 (9) | 0.0442 (13) | 0.0039 (10) |
N3 | 0.0540 (16) | 0.0231 (12) | 0.0646 (18) | 0.0040 (11) | 0.0344 (15) | 0.0036 (11) |
N4 | 0.0536 (17) | 0.0377 (15) | 0.0720 (19) | 0.0088 (12) | 0.0345 (16) | −0.0041 (14) |
C14 | 0.061 (2) | 0.0343 (17) | 0.048 (2) | 0.0070 (15) | 0.0241 (17) | 0.0007 (15) |
C15 | 0.085 (3) | 0.0423 (19) | 0.052 (2) | 0.0197 (19) | 0.035 (2) | 0.0005 (16) |
C16 | 0.076 (3) | 0.064 (2) | 0.065 (3) | 0.037 (2) | 0.040 (2) | 0.0085 (19) |
C17 | 0.056 (2) | 0.073 (3) | 0.067 (3) | 0.0151 (19) | 0.032 (2) | −0.002 (2) |
C18 | 0.053 (2) | 0.0454 (19) | 0.057 (2) | 0.0035 (16) | 0.0296 (18) | −0.0038 (16) |
C19 | 0.051 (2) | 0.0320 (16) | 0.0466 (19) | 0.0093 (14) | 0.0301 (17) | 0.0054 (14) |
C20 | 0.0459 (19) | 0.0277 (15) | 0.0465 (19) | 0.0056 (13) | 0.0208 (16) | −0.0012 (13) |
C21 | 0.053 (2) | 0.0390 (18) | 0.071 (2) | 0.0089 (15) | 0.0378 (19) | 0.0038 (16) |
C22 | 0.0389 (17) | 0.0346 (17) | 0.048 (2) | 0.0070 (13) | 0.0183 (16) | 0.0008 (14) |
C23 | 0.061 (2) | 0.0471 (19) | 0.057 (2) | 0.0159 (16) | 0.0345 (19) | 0.0025 (16) |
C24 | 0.064 (2) | 0.0401 (19) | 0.069 (2) | 0.0109 (16) | 0.036 (2) | 0.0083 (17) |
C25 | 0.064 (2) | 0.0468 (19) | 0.077 (3) | 0.0113 (17) | 0.044 (2) | −0.0046 (18) |
C26 | 0.062 (2) | 0.0464 (19) | 0.069 (2) | 0.0129 (16) | 0.043 (2) | 0.0065 (17) |
Geometric parameters (Å, º) top
S1—C7 | 1.642 (3) | S2—C20 | 1.651 (3) |
O1—C7 | 1.358 (3) | O2—C20 | 1.351 (3) |
O1—C8 | 1.432 (3) | O2—C21 | 1.435 (3) |
N1—C7 | 1.339 (3) | N3—C20 | 1.333 (3) |
N1—C6 | 1.414 (3) | N3—C19 | 1.422 (3) |
N1—H1A | 0.8600 | N3—H3B | 0.8600 |
N2—C12 | 1.328 (4) | N4—C24 | 1.322 (4) |
N2—C11 | 1.336 (4) | N4—C25 | 1.336 (4) |
C1—C2 | 1.383 (4) | C14—C19 | 1.378 (4) |
C1—C6 | 1.389 (4) | C14—C15 | 1.386 (4) |
C1—H1B | 0.9300 | C14—H14A | 0.9300 |
C2—C3 | 1.368 (4) | C15—C16 | 1.381 (5) |
C2—H2B | 0.9300 | C15—H15A | 0.9300 |
C3—C4 | 1.373 (4) | C16—C17 | 1.369 (4) |
C3—H3A | 0.9300 | C16—H16A | 0.9300 |
C4—C5 | 1.384 (4) | C17—C18 | 1.380 (4) |
C4—H4A | 0.9300 | C17—H17A | 0.9300 |
C5—C6 | 1.379 (4) | C18—C19 | 1.387 (4) |
C5—H5A | 0.9300 | C18—H18A | 0.9300 |
C8—C9 | 1.495 (4) | C21—C22 | 1.501 (4) |
C8—H8A | 0.9700 | C21—H21A | 0.9700 |
C8—H8B | 0.9700 | C21—H21B | 0.9700 |
C9—C13 | 1.366 (4) | C22—C23 | 1.380 (4) |
C9—C10 | 1.377 (4) | C22—C26 | 1.383 (4) |
C10—C11 | 1.373 (4) | C23—C24 | 1.384 (4) |
C10—H10A | 0.9300 | C23—H23A | 0.9300 |
C11—H11A | 0.9300 | C24—H24A | 0.9300 |
C12—C13 | 1.388 (4) | C25—C26 | 1.382 (4) |
C12—H12A | 0.9300 | C25—H25A | 0.9300 |
C13—H13A | 0.9300 | C26—H26A | 0.9300 |
| | | |
C7—O1—C8 | 120.1 (2) | C20—O2—C21 | 119.3 (2) |
C7—N1—C6 | 129.8 (2) | C20—N3—C19 | 128.1 (2) |
C7—N1—H1A | 115.1 | C20—N3—H3B | 116.0 |
C6—N1—H1A | 115.1 | C19—N3—H3B | 116.0 |
C12—N2—C11 | 116.8 (3) | C24—N4—C25 | 116.3 (3) |
C2—C1—C6 | 119.1 (3) | C19—C14—C15 | 119.7 (3) |
C2—C1—H1B | 120.4 | C19—C14—H14A | 120.1 |
C6—C1—H1B | 120.4 | C15—C14—H14A | 120.1 |
C3—C2—C1 | 121.5 (3) | C16—C15—C14 | 120.2 (3) |
C3—C2—H2B | 119.3 | C16—C15—H15A | 119.9 |
C1—C2—H2B | 119.3 | C14—C15—H15A | 119.9 |
C2—C3—C4 | 119.6 (3) | C17—C16—C15 | 120.1 (3) |
C2—C3—H3A | 120.2 | C17—C16—H16A | 120.0 |
C4—C3—H3A | 120.2 | C15—C16—H16A | 120.0 |
C3—C4—C5 | 119.7 (3) | C16—C17—C18 | 120.0 (3) |
C3—C4—H4A | 120.2 | C16—C17—H17A | 120.0 |
C5—C4—H4A | 120.2 | C18—C17—H17A | 120.0 |
C6—C5—C4 | 121.0 (3) | C17—C18—C19 | 120.3 (3) |
C6—C5—H5A | 119.5 | C17—C18—H18A | 119.9 |
C4—C5—H5A | 119.5 | C19—C18—H18A | 119.9 |
C5—C6—C1 | 119.1 (3) | C14—C19—C18 | 119.6 (3) |
C5—C6—N1 | 116.5 (3) | C14—C19—N3 | 123.4 (3) |
C1—C6—N1 | 124.3 (3) | C18—C19—N3 | 117.0 (3) |
N1—C7—O1 | 107.1 (2) | N3—C20—O2 | 107.6 (2) |
N1—C7—S1 | 129.3 (2) | N3—C20—S2 | 128.2 (2) |
O1—C7—S1 | 123.6 (2) | O2—C20—S2 | 124.3 (2) |
O1—C8—C9 | 104.9 (2) | O2—C21—C22 | 107.7 (2) |
O1—C8—H8A | 110.8 | O2—C21—H21A | 110.2 |
C9—C8—H8A | 110.8 | C22—C21—H21A | 110.2 |
O1—C8—H8B | 110.8 | O2—C21—H21B | 110.2 |
C9—C8—H8B | 110.8 | C22—C21—H21B | 110.2 |
H8A—C8—H8B | 108.8 | H21A—C21—H21B | 108.5 |
C13—C9—C10 | 117.3 (3) | C23—C22—C26 | 116.7 (3) |
C13—C9—C8 | 121.5 (3) | C23—C22—C21 | 123.5 (3) |
C10—C9—C8 | 121.1 (3) | C26—C22—C21 | 119.8 (3) |
C11—C10—C9 | 120.5 (3) | C22—C23—C24 | 119.7 (3) |
C11—C10—H10A | 119.7 | C22—C23—H23A | 120.2 |
C9—C10—H10A | 119.7 | C24—C23—H23A | 120.2 |
N2—C11—C10 | 122.5 (3) | N4—C24—C23 | 124.0 (3) |
N2—C11—H11A | 118.7 | N4—C24—H24A | 118.0 |
C10—C11—H11A | 118.7 | C23—C24—H24A | 118.0 |
N2—C12—C13 | 123.8 (3) | N4—C25—C26 | 123.6 (3) |
N2—C12—H12A | 118.1 | N4—C25—H25A | 118.2 |
C13—C12—H12A | 118.1 | C26—C25—H25A | 118.2 |
C9—C13—C12 | 119.1 (3) | C25—C26—C22 | 119.7 (3) |
C9—C13—H13A | 120.4 | C25—C26—H26A | 120.2 |
C12—C13—H13A | 120.4 | C22—C26—H26A | 120.2 |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···N4i | 0.86 | 2.12 | 2.966 (3) | 170 |
N3—H3B···N2ii | 0.86 | 2.07 | 2.910 (3) | 164 |
C10—H10A···Cg1iii | 0.93 | 2.86 | 3.757 (2) | 162 |
C13—H13A···Cg1 | 0.93 | 2.80 | 3.686 (1) | 161 |
C23—H23A···Cg2ii | 0.93 | 3.08 | 3.685 (2) | 125 |
C26—H26A···Cg3 | 0.93 | 2.96 | 3.718 (2) | 140 |
Symmetry codes: (i) −x+1, y−1/2, −z+1/2; (ii) −x+2, y+1/2, −z+1/2; (iii) x, −y+1/2, z+1/2. |