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Acta Crystallogr Sect E Struct Rep Online. 2008 May 1; 64(Pt 5): o901.
Published online 2008 April 23. doi:  10.1107/S1600536808010854
PMCID: PMC2961214

1,3-Bis[4-(4-pyrid­yl)pyrimidin-2-ylsulfan­yl]propane

Abstract

In the title compound, C21H18N6S2, the dihedral angles between the aromatic rings in the two 4-(4-pyrid­yl)pyrimidine residues are 23.45 (13) and 2.67 (14)°. Whereas one of the C—S—C—C torsion angles corresponds to a staggered conformation, the other is gauche.

Related literature

For related structures, see: Awaleh et al. (2005 [triangle]); Xie et al. (2005 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-0o901-scheme1.jpg

Experimental

Crystal data

  • C21H18N6S2
  • M r = 418.55
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-0o901-efi1.jpg
  • a = 9.986 (3) Å
  • b = 10.057 (3) Å
  • c = 10.645 (3) Å
  • α = 98.972 (5)°
  • β = 90.688 (5)°
  • γ = 112.632 (5)°
  • V = 971.6 (5) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 0.29 mm−1
  • T = 291 (2) K
  • 0.30 × 0.20 × 0.20 mm

Data collection

  • Bruker SMART CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2000 [triangle]) T min = 0.915, T max = 0.943
  • 5163 measured reflections
  • 3720 independent reflections
  • 2986 reflections with I > 2σ(I)
  • R int = 0.028

Refinement

  • R[F 2 > 2σ(F 2)] = 0.059
  • wR(F 2) = 0.156
  • S = 1.02
  • 3720 reflections
  • 262 parameters
  • H-atom parameters constrained
  • Δρmax = 0.52 e Å−3
  • Δρmin = −0.46 e Å−3

Data collection: SMART (Bruker, 2000 [triangle]); cell refinement: SMART; data reduction: SAINT (Bruker, 2000 [triangle]); program(s) used to solve structure: SHELXTL (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808010854/bt2695sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808010854/bt2695Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

The authors thank the Program for Excellent Talents Introduction of Southeast University for financial support.

supplementary crystallographic information

Comment

In the title compound, the dihedral angles between the aromatic rings in the two(4-pyridyl)-pyrimidine residues are 23.45 (13)° and 2.67 (14)°. Whereas one of the C-S-C-C torsion angles adopts a staggered conformation [-176.74 (17)°], the other one is gauche [87.6 (2)°].

Experimental

NaOH (0.80 g, 20 mmol) in ethanol (10 mL) was added with stirring to a solution of 4-(pyridin-4-yl)pyrimidine-2-thiol (3.78 g, 20 mmol) in acetone (30 mL) at ambient temperature for 20 min. A solution of 1,3-dibromopropane (2.00 g, 10.0 mmol) was added slowly over 1 h, and the resulting mixture was further refluxed for 6 h. The solids isolated from the reaction mixture were washed with water and acetone. The yellow products were obtained by vacuum dryness in 91% yield (3.80 g). The filtrate was allowed to evaporate slowly at room temperature. After several days, yellow block shaped crystals suitable for X-ray diffraction analyses were obtained.

Refinement

H atoms were positioned geometrically and refined using a riding model, with C—H = 0.93 and 0.97 Å for Caromatic and Cmethylene, respectively, and with Uiso(H) = 1.2Ueq(C).

Figures

Fig. 1.
The molecular structure of the title compound.

Crystal data

C21H18N6S2Z = 2
Mr = 418.55F000 = 436.0
Triclinic, P1Dx = 1.431 Mg m3
Hall symbol: -P 1Mo Kα radiation λ = 0.71073 Å
a = 9.986 (3) ÅCell parameters from 765 reflections
b = 10.057 (3) Åθ = 2.5–28.0º
c = 10.645 (3) ŵ = 0.30 mm1
α = 98.972 (5)ºT = 291 (2) K
β = 90.688 (5)ºBlock, yellow
γ = 112.632 (5)º0.30 × 0.20 × 0.20 mm
V = 971.6 (5) Å3

Data collection

Bruker CCD area-detector diffractometer3720 independent reflections
Radiation source: fine-focus sealed tube2986 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.028
T = 291(2) Kθmax = 26.0º
[var phi] and ω scansθmin = 1.9º
Absorption correction: multi-scan(SADABS; Bruker, 2000)h = −12→11
Tmin = 0.915, Tmax = 0.943k = −12→10
5163 measured reflectionsl = −12→13

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.059H-atom parameters constrained
wR(F2) = 0.156  w = 1/[σ2(Fo2) + (0.1031P)2] where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max < 0.001
3720 reflectionsΔρmax = 0.52 e Å3
262 parametersΔρmin = −0.46 e Å3
Primary atom site location: structure-invariant direct methodsExtinction correction: none

Special details

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)

xyzUiso*/Ueq
S10.66814 (7)0.18543 (8)0.02844 (6)0.0501 (2)
S20.31122 (8)0.33035 (8)0.24761 (7)0.0551 (2)
N10.9037 (2)0.1412 (2)−0.0039 (2)0.0484 (5)
N20.88209 (19)0.3272 (2)−0.10815 (17)0.0362 (4)
N31.1505 (2)0.6455 (2)−0.4191 (2)0.0517 (6)
N40.1388 (2)0.1026 (2)0.3337 (2)0.0516 (5)
N50.3748 (2)0.1065 (2)0.29548 (17)0.0394 (5)
N60.6716 (3)−0.1928 (3)0.3320 (2)0.0558 (6)
C10.8365 (2)0.2254 (3)−0.0352 (2)0.0374 (5)
C21.0326 (3)0.1682 (3)−0.0486 (2)0.0488 (6)
H21.08590.1158−0.02700.059*
C31.0916 (3)0.2709 (3)−0.1260 (2)0.0449 (6)
H31.18260.2879−0.15650.054*
C41.0107 (2)0.3474 (2)−0.1565 (2)0.0346 (5)
C51.0584 (2)0.4510 (2)−0.2471 (2)0.0355 (5)
C61.1556 (3)0.4399 (3)−0.3360 (2)0.0438 (6)
H61.19250.3676−0.33970.053*
C71.1961 (3)0.5387 (3)−0.4185 (3)0.0520 (7)
H71.26050.5294−0.47840.062*
C81.0070 (3)0.5595 (3)−0.2489 (2)0.0423 (6)
H80.93920.5687−0.19280.051*
C91.0560 (3)0.6538 (3)−0.3333 (3)0.0504 (6)
H91.02160.7279−0.33110.061*
C100.6054 (3)0.3160 (3)−0.0212 (2)0.0454 (6)
H10A0.67650.41460.00800.055*
H10B0.59200.2998−0.11350.055*
C110.4614 (3)0.2964 (3)0.0364 (2)0.0475 (6)
H11A0.41090.3412−0.01010.057*
H11B0.40110.19280.02630.057*
C120.4802 (3)0.3627 (3)0.1758 (2)0.0446 (6)
H12A0.53520.46740.18520.054*
H12B0.53670.32280.22130.054*
C130.2733 (3)0.1608 (3)0.2964 (2)0.0416 (5)
C140.1092 (3)−0.0215 (3)0.3770 (2)0.0519 (7)
H140.0168−0.06730.40370.062*
C150.2062 (3)−0.0862 (3)0.3847 (2)0.0464 (6)
H150.1824−0.17200.41790.056*
C160.3416 (3)−0.0181 (2)0.3409 (2)0.0373 (5)
C170.4557 (3)−0.0781 (2)0.3402 (2)0.0373 (5)
C180.4364 (3)−0.2049 (3)0.3858 (2)0.0491 (6)
H180.3500−0.25500.42040.059*
C190.5447 (3)−0.2568 (3)0.3800 (2)0.0546 (7)
H190.5286−0.34230.41170.066*
C200.5885 (3)−0.0082 (3)0.2938 (2)0.0443 (6)
H200.60920.07980.26500.053*
C210.6903 (3)−0.0697 (3)0.2905 (3)0.0536 (7)
H210.7781−0.02170.25690.064*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
S10.0461 (4)0.0571 (4)0.0600 (4)0.0260 (3)0.0245 (3)0.0303 (3)
S20.0617 (5)0.0605 (4)0.0689 (5)0.0449 (4)0.0295 (4)0.0283 (4)
N10.0516 (13)0.0521 (12)0.0558 (13)0.0287 (10)0.0163 (10)0.0272 (10)
N20.0346 (10)0.0392 (10)0.0392 (10)0.0173 (8)0.0077 (8)0.0118 (8)
N30.0481 (13)0.0537 (13)0.0615 (14)0.0215 (10)0.0138 (10)0.0283 (11)
N40.0447 (12)0.0597 (14)0.0598 (13)0.0287 (11)0.0183 (10)0.0142 (11)
N50.0438 (11)0.0451 (11)0.0400 (10)0.0264 (9)0.0124 (8)0.0134 (8)
N60.0701 (16)0.0584 (13)0.0590 (14)0.0434 (12)0.0147 (12)0.0192 (11)
C10.0389 (12)0.0410 (12)0.0381 (12)0.0193 (10)0.0083 (10)0.0132 (10)
C20.0470 (14)0.0536 (15)0.0620 (16)0.0306 (12)0.0109 (12)0.0270 (12)
C30.0391 (13)0.0505 (14)0.0575 (15)0.0257 (11)0.0139 (11)0.0226 (12)
C40.0326 (11)0.0355 (11)0.0385 (12)0.0148 (9)0.0052 (9)0.0103 (9)
C50.0296 (11)0.0382 (12)0.0414 (12)0.0145 (9)0.0036 (9)0.0113 (9)
C60.0381 (13)0.0482 (14)0.0553 (14)0.0232 (11)0.0144 (11)0.0206 (11)
C70.0458 (15)0.0595 (16)0.0604 (16)0.0242 (13)0.0210 (12)0.0277 (13)
C80.0409 (13)0.0445 (13)0.0485 (13)0.0219 (11)0.0099 (10)0.0139 (11)
C90.0516 (15)0.0439 (14)0.0654 (16)0.0244 (12)0.0104 (13)0.0218 (12)
C100.0450 (14)0.0548 (15)0.0446 (13)0.0251 (12)0.0125 (11)0.0164 (11)
C110.0392 (13)0.0628 (16)0.0494 (14)0.0265 (12)0.0092 (11)0.0172 (12)
C120.0447 (14)0.0477 (13)0.0508 (14)0.0251 (11)0.0122 (11)0.0160 (11)
C130.0477 (14)0.0485 (13)0.0392 (12)0.0294 (11)0.0123 (10)0.0097 (10)
C140.0455 (15)0.0552 (15)0.0556 (15)0.0197 (12)0.0189 (12)0.0098 (12)
C150.0501 (15)0.0438 (13)0.0455 (14)0.0172 (12)0.0153 (11)0.0109 (11)
C160.0441 (13)0.0399 (12)0.0309 (11)0.0200 (10)0.0073 (9)0.0057 (9)
C170.0488 (14)0.0389 (12)0.0299 (11)0.0226 (10)0.0091 (9)0.0077 (9)
C180.0627 (16)0.0483 (14)0.0488 (14)0.0303 (13)0.0199 (12)0.0201 (11)
C190.080 (2)0.0489 (15)0.0537 (15)0.0400 (14)0.0211 (14)0.0233 (12)
C200.0506 (15)0.0425 (13)0.0508 (14)0.0256 (11)0.0134 (11)0.0193 (11)
C210.0560 (16)0.0590 (16)0.0627 (16)0.0353 (14)0.0207 (13)0.0242 (13)

Geometric parameters (Å, °)

S1—C11.743 (2)C7—H70.9300
S1—C101.799 (3)C8—C91.365 (3)
S2—C131.762 (3)C8—H80.9300
S2—C121.796 (2)C9—H90.9300
N1—C21.320 (3)C10—C111.525 (3)
N1—C11.342 (3)C10—H10A0.9700
N2—C11.325 (3)C10—H10B0.9700
N2—C41.343 (3)C11—C121.507 (3)
N3—C71.320 (3)C11—H11A0.9700
N3—C91.338 (3)C11—H11B0.9700
N4—C141.325 (3)C12—H12A0.9700
N4—C131.336 (3)C12—H12B0.9700
N5—C131.323 (3)C14—C151.367 (4)
N5—C161.337 (3)C14—H140.9300
N6—C211.326 (3)C15—C161.385 (3)
N6—C191.330 (4)C15—H150.9300
C2—C31.379 (3)C16—C171.480 (3)
C2—H20.9300C17—C181.381 (3)
C3—C41.379 (3)C17—C201.380 (3)
C3—H30.9300C18—C191.368 (4)
C4—C51.478 (3)C18—H180.9300
C5—C81.376 (3)C19—H190.9300
C5—C61.386 (3)C20—C211.377 (4)
C6—C71.376 (3)C20—H200.9300
C6—H60.9300C21—H210.9300
C1—S1—C10103.68 (11)H10A—C10—H10B108.4
C13—S2—C12102.41 (11)C12—C11—C10113.0 (2)
C2—N1—C1114.9 (2)C12—C11—H11A109.0
C1—N2—C4115.73 (19)C10—C11—H11A109.0
C7—N3—C9115.9 (2)C12—C11—H11B109.0
C14—N4—C13114.3 (2)C10—C11—H11B109.0
C13—N5—C16116.7 (2)H11A—C11—H11B107.8
C21—N6—C19115.5 (2)C11—C12—S2113.52 (17)
N2—C1—N1127.7 (2)C11—C12—H12A108.9
N2—C1—S1119.77 (17)S2—C12—H12A108.9
N1—C1—S1112.50 (17)C11—C12—H12B108.9
N1—C2—C3122.8 (2)S2—C12—H12B108.9
N1—C2—H2118.6H12A—C12—H12B107.7
C3—C2—H2118.6N5—C13—N4127.3 (2)
C4—C3—C2117.5 (2)N5—C13—S2119.94 (18)
C4—C3—H3121.2N4—C13—S2112.72 (18)
C2—C3—H3121.2N4—C14—C15124.0 (2)
N2—C4—C3121.2 (2)N4—C14—H14118.0
N2—C4—C5116.95 (19)C15—C14—H14118.0
C3—C4—C5121.8 (2)C14—C15—C16116.9 (2)
C8—C5—C6117.4 (2)C14—C15—H15121.6
C8—C5—C4122.0 (2)C16—C15—H15121.6
C6—C5—C4120.6 (2)N5—C16—C15120.7 (2)
C7—C6—C5118.4 (2)N5—C16—C17116.6 (2)
C7—C6—H6120.8C15—C16—C17122.7 (2)
C5—C6—H6120.8C18—C17—C20116.4 (2)
N3—C7—C6124.9 (2)C18—C17—C16122.6 (2)
N3—C7—H7117.6C20—C17—C16121.0 (2)
C6—C7—H7117.6C19—C18—C17119.9 (2)
C9—C8—C5119.8 (2)C19—C18—H18120.1
C9—C8—H8120.1C17—C18—H18120.1
C5—C8—H8120.1N6—C19—C18124.3 (2)
N3—C9—C8123.7 (2)N6—C19—H19117.8
N3—C9—H9118.1C18—C19—H19117.8
C8—C9—H9118.1C21—C20—C17119.5 (2)
C11—C10—S1108.09 (17)C21—C20—H20120.3
C11—C10—H10A110.1C17—C20—H20120.3
S1—C10—H10A110.1N6—C21—C20124.4 (2)
C11—C10—H10B110.1N6—C21—H21117.8
S1—C10—H10B110.1C20—C21—H21117.8

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT2695).

References

  • Awaleh, M. O., Badia, A. & Brisse, F. (2005). Inorg. Chem.44, 7833–7845. [PubMed]
  • Bruker (2000). SMART, SAINT and SADABS Bruker AXS Inc., Madison, Wisconsin, USA.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Xie, Y.-B., Li, J.-R., Zhang, C. & Bu, X.-H. (2005). Cryst. Growth Des.5, 1743–1749.

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