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Acta Crystallogr Sect E Struct Rep Online. 2010 March 1; 66(Pt 3): o635.
Published online 2010 February 13. doi:  10.1107/S1600536810004708
PMCID: PMC2983710

4,4,6-Trimethyl-1-(3-methyl­phen­yl)-3,4-dihydro­pyrimidine-2(1H)-thione

Abstract

The asymmetric unit of the title compound, C14H18N2S, contains two independent and conformationally similar mol­ecules, which form cyclic dimers via inter­molecular hydrogen bonds of the type N—H(...)S [graph set R 2 2(8)]. The structure is iso­morphous with that of one of the polymorphs of 4,4,6-tri­methyl-1-phenyl-3,4-dihydro­pyrimidine-2(1H)-thione [Yam­in et al. (2005 [triangle]). Acta Cryst. E61, o55–o57].

Related literature

For the biological activity of pyrimidine-2-thio­nes, see: Alam et al. (2005 [triangle]); Sriram et al. (2006 [triangle]); Swamy et al. (2005 [triangle]). For related structures, see: Yamin et al. (2005 [triangle]); Ismail et al. (2007 [triangle]). For graph-set analysis, see Etter et al. (1990 [triangle]).

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Object name is e-66-0o635-scheme1.jpg

Experimental

Crystal data

  • C14H18N2S
  • M r = 246.36
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-66-0o635-efi1.jpg
  • a = 10.5904 (3) Å
  • b = 16.9189 (5) Å
  • c = 30.5713 (10) Å
  • V = 5477.7 (3) Å3
  • Z = 16
  • Mo Kα radiation
  • μ = 0.22 mm−1
  • T = 173 K
  • 0.14 × 0.12 × 0.08 mm

Data collection

  • Bruker APEXII CCD diffractometer
  • Absorption correction: multi-scan (SORTAV; Blessing, 1997 [triangle]) T min = 0.970, T max = 0.983
  • 19135 measured reflections
  • 4830 independent reflections
  • 3231 reflections with I > 2.0σ(I)
  • R int = 0.041

Refinement

  • R[F 2 > 2σ(F 2)] = 0.049
  • wR(F 2) = 0.115
  • S = 1.04
  • 4830 reflections
  • 315 parameters
  • H-atom parameters constrained
  • Δρmax = 0.25 e Å−3
  • Δρmin = −0.23 e Å−3

Data collection: COLLECT (Hooft, 1998 [triangle]); cell refinement: HKL DENZO (Otwinowski & Minor, 1997 [triangle]); data reduction: SCALEPACK (Otwinowski & Minor, 1997 [triangle]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 [triangle]); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks Global, I. DOI: 10.1107/S1600536810004708/zs2028sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810004708/zs2028Isup2.hkl

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

Acknowledgments

The authors gratefully acknowledge a research grant from the Higher Education Commission of Pakistan under project No. 20-Miscel/R&D/00/3834.

supplementary crystallographic information

Comment

The title compound C14H18N2S (I) belongs to a novel and rare class of dihydropyrimidine-2-thiones. Their synthesis has been attracting widespread attention because of their diverse pharmacological properties such as antibacterial (Alam et al., 2005), antitumour (Swamy et al., 2005) and antioxidative activities (Sriram et al., 2006). The crystal structure of a closely related compound, 4,4,6-trimethyl-1-phenyl-3,4-dihydropyrimidine-2(1H)-thione (Yamin et al., 2005) and its triclinic polymorph (Ismail et al., 2007) have been reported.

The asymmetric unit of the title compound is composed of two molecules (Fig. 1) exhibiting intermolecular hydrogen bonds of the type N—H···S (Table 1) forming cyclic dimers [graph set R22(8) (Etter et al., 1990)]. The two molecules are conformationally similar [e.g. the inter-ring torsion angle C1–N2–C8–C13 (molecule 1), -83.1 (3)° and C15–N4–C22–C27, -85.9 (3)° (molecule 2)] and are related by pseudo two-fold rotational symmetry. The title compound is isomorphous with one of the polymorphs of 4,4,6-trimethyl-1-phenyl-3,4-dihydropyrimidine-2(1H)-thione (Yamin et al., 2005). However, in the triclinic polymorph of this related compound (Ismail et al., 2007), which also forms a cyclic dimer, the two molecules have crystallographic inversion symmetry.

Experimental

The title compound was prepared by the reaction of 3-methylaniline with 4-methylpent-3-en-2-one in the presence of potassium thiocyanate in acetone: details of the synthesis will be reported later. Recrystallization from methanol afforded the title compound as colourless crystals: Anal. calcd. for C14H18N2S: C, 68.25; H, 7.36; N, 11.37; S, 13.01%; found: C, 68.09; H, 7.41; N, 11.51; S, 13.12.

Refinement

All H-atoms were visible in the difference Fourier maps but were included in the refinements at geometrically idealized positions with distances: N—H = 0.88 Å and C—H = 0.95 and 0.98 Å, with Uiso = 1.2Ueq of the atoms to which they were bonded. The final difference map was free of chemically significant features.

Figures

Fig. 1.
ORTEP-3 (Farrugia, 1997) drawing of the two molecules in the asymmetric unit of (I) with displacement ellipsoids plotted at 50% probability level. Hydrogen bonds have been drawn with dashed lines.

Crystal data

C14H18N2SF(000) = 2112
Mr = 246.36Dx = 1.195 Mg m3
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 8634 reflections
a = 10.5904 (3) Åθ = 1.0–25.3°
b = 16.9189 (5) ŵ = 0.22 mm1
c = 30.5713 (10) ÅT = 173 K
V = 5477.7 (3) Å3Block, colorless
Z = 160.14 × 0.12 × 0.08 mm

Data collection

Bruker APEXII CCD diffractometer4830 independent reflections
Radiation source: fine-focus sealed tube3231 reflections with I > 2.0σ(I)
graphiteRint = 0.041
[var phi] & ω scansθmax = 25.3°, θmin = 2.3°
Absorption correction: multi-scan (SORTAV; Blessing, 1997)h = −12→12
Tmin = 0.970, Tmax = 0.983k = −20→20
19135 measured reflectionsl = −36→36

Refinement

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) = 0.115H-atom parameters constrained
S = 1.04w = 1/[σ2(Fo2) + (0.038P)2 + 3.05P] where P = (Fo2 + 2Fc2)/3
4830 reflections(Δ/σ)max < 0.001
315 parametersΔρmax = 0.25 e Å3
0 restraintsΔρmin = −0.23 e Å3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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
S10.85314 (7)0.07897 (4)0.325070 (19)0.03644 (19)
S20.84290 (7)0.24913 (4)0.43316 (2)0.03863 (19)
N10.75860 (19)0.22309 (11)0.32616 (6)0.0343 (5)
H1N0.75790.21640.35470.041*
N20.76802 (18)0.16559 (11)0.25790 (6)0.0305 (5)
N30.7806 (2)0.09853 (11)0.43444 (6)0.0376 (5)
H3N0.78970.10320.40600.045*
N40.7743 (2)0.16054 (12)0.50157 (6)0.0354 (5)
C10.7907 (2)0.16081 (13)0.30203 (7)0.0285 (6)
C20.7240 (2)0.30212 (14)0.30983 (8)0.0327 (6)
C30.6741 (2)0.29264 (14)0.26468 (8)0.0365 (6)
H30.62200.33320.25300.044*
C40.6990 (2)0.23009 (14)0.23982 (8)0.0325 (6)
C50.6260 (3)0.33607 (17)0.34098 (9)0.0513 (8)
H5A0.60520.39020.33210.062*
H5B0.66010.33650.37080.062*
H5C0.54960.30340.34010.062*
C60.8409 (3)0.35435 (16)0.31010 (10)0.0476 (7)
H6A0.81820.40770.30030.057*
H6B0.90450.33210.29030.057*
H6C0.87530.35690.33980.057*
C70.6571 (3)0.22143 (16)0.19344 (8)0.0440 (7)
H7A0.61240.26940.18430.053*
H7B0.60030.17590.19090.053*
H7C0.73090.21330.17460.053*
C80.8098 (2)0.10194 (14)0.23002 (7)0.0293 (6)
C90.7269 (2)0.04236 (14)0.21939 (7)0.0316 (6)
H90.64330.04320.23060.038*
C100.7653 (2)−0.01925 (14)0.19210 (8)0.0346 (6)
C110.8885 (3)−0.01932 (15)0.17714 (8)0.0380 (6)
H110.9167−0.06170.15920.046*
C120.9715 (2)0.04068 (16)0.18757 (8)0.0386 (6)
H121.05540.03970.17660.046*
C130.9320 (2)0.10269 (15)0.21418 (7)0.0339 (6)
H130.98790.14470.22130.041*
C140.6721 (3)−0.08216 (16)0.17965 (9)0.0494 (8)
H14A0.7167−0.12640.16580.059*
H14B0.6104−0.06020.15910.059*
H14C0.6283−0.10090.20590.059*
C150.7974 (2)0.16412 (14)0.45766 (8)0.0325 (6)
C160.7484 (3)0.01867 (14)0.45061 (8)0.0390 (7)
C170.7067 (3)0.02656 (17)0.49684 (9)0.0549 (8)
H170.6667−0.01760.51010.066*
C180.7217 (3)0.09111 (15)0.52074 (8)0.0420 (7)
C190.8654 (3)−0.03424 (16)0.44798 (10)0.0569 (8)
H19A0.8435−0.08780.45760.068*
H19B0.9317−0.01290.46700.068*
H19C0.8959−0.03590.41770.068*
C200.6454 (3)−0.01520 (17)0.42148 (10)0.0532 (8)
H20A0.6238−0.06860.43140.064*
H20B0.6756−0.01740.39120.064*
H20C0.57040.01860.42300.064*
C210.6857 (4)0.09640 (19)0.56755 (10)0.0709 (10)
H21A0.65610.04470.57770.085*
H21B0.61800.13540.57100.085*
H21C0.75910.11270.58490.085*
C220.8055 (2)0.22713 (14)0.52939 (8)0.0331 (6)
C230.7123 (2)0.27825 (15)0.54251 (8)0.0355 (6)
H230.62880.27180.53170.043*
C240.7391 (3)0.33970 (15)0.57156 (8)0.0381 (6)
C250.8616 (3)0.34748 (16)0.58649 (8)0.0425 (7)
H250.88150.38870.60640.051*
C260.9557 (3)0.29648 (17)0.57300 (8)0.0464 (7)
H261.03960.30330.58330.056*
C270.9278 (3)0.23536 (16)0.54441 (8)0.0403 (7)
H270.99180.19970.53530.048*
C280.6363 (3)0.39498 (17)0.58604 (10)0.0541 (8)
H28A0.66590.42600.61110.065*
H28B0.56170.36440.59450.065*
H28C0.61440.43060.56190.065*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
S10.0510 (4)0.0257 (3)0.0326 (3)0.0049 (3)−0.0024 (3)0.0000 (3)
S20.0582 (5)0.0254 (3)0.0322 (3)−0.0035 (3)−0.0002 (3)0.0002 (3)
N10.0497 (13)0.0252 (11)0.0281 (10)0.0039 (10)0.0008 (10)−0.0014 (9)
N20.0352 (12)0.0272 (11)0.0292 (10)0.0041 (10)−0.0024 (10)−0.0019 (9)
N30.0615 (15)0.0240 (11)0.0274 (11)−0.0043 (11)0.0009 (11)−0.0011 (9)
N40.0493 (14)0.0276 (11)0.0291 (11)−0.0034 (11)0.0026 (10)−0.0016 (9)
C10.0295 (13)0.0243 (13)0.0318 (13)−0.0033 (11)0.0000 (11)−0.0012 (10)
C20.0375 (15)0.0245 (13)0.0362 (13)0.0026 (12)−0.0003 (12)−0.0029 (11)
C30.0383 (15)0.0272 (14)0.0439 (15)0.0046 (12)−0.0074 (13)0.0029 (12)
C40.0326 (14)0.0304 (14)0.0345 (14)0.0000 (12)−0.0033 (12)0.0016 (11)
C50.0586 (19)0.0457 (18)0.0495 (16)0.0192 (16)0.0048 (15)−0.0015 (14)
C60.0503 (18)0.0360 (16)0.0564 (17)−0.0044 (14)−0.0067 (15)0.0013 (13)
C70.0522 (18)0.0370 (16)0.0427 (15)0.0072 (14)−0.0087 (14)0.0001 (12)
C80.0337 (15)0.0272 (13)0.0270 (12)0.0039 (12)−0.0030 (11)0.0003 (10)
C90.0310 (14)0.0335 (14)0.0304 (13)0.0018 (12)0.0000 (11)0.0007 (11)
C100.0437 (16)0.0299 (14)0.0300 (13)0.0001 (13)−0.0069 (12)0.0011 (11)
C110.0471 (17)0.0375 (16)0.0293 (13)0.0127 (14)−0.0058 (13)−0.0053 (12)
C120.0360 (15)0.0475 (17)0.0324 (14)0.0066 (14)0.0006 (12)−0.0001 (13)
C130.0338 (15)0.0375 (15)0.0305 (13)−0.0008 (12)−0.0011 (12)−0.0006 (11)
C140.061 (2)0.0392 (16)0.0475 (16)−0.0060 (15)−0.0062 (15)−0.0059 (13)
C150.0375 (15)0.0285 (14)0.0316 (13)0.0011 (12)−0.0027 (11)−0.0003 (11)
C160.0558 (18)0.0235 (14)0.0378 (15)−0.0044 (13)0.0016 (14)0.0008 (11)
C170.083 (2)0.0356 (17)0.0457 (17)−0.0191 (17)0.0134 (16)0.0015 (13)
C180.0555 (18)0.0337 (15)0.0369 (14)−0.0072 (14)0.0043 (14)0.0028 (12)
C190.067 (2)0.0353 (17)0.068 (2)0.0020 (16)−0.0107 (17)0.0072 (15)
C200.060 (2)0.0351 (16)0.0645 (19)−0.0108 (15)−0.0136 (16)0.0014 (14)
C210.114 (3)0.054 (2)0.0451 (17)−0.026 (2)0.0167 (19)0.0044 (15)
C220.0427 (16)0.0287 (14)0.0278 (12)−0.0003 (13)0.0009 (12)−0.0017 (10)
C230.0359 (15)0.0386 (15)0.0319 (13)−0.0014 (13)−0.0031 (12)−0.0013 (12)
C240.0479 (17)0.0339 (15)0.0325 (13)0.0029 (14)0.0026 (13)−0.0058 (12)
C250.0503 (18)0.0429 (17)0.0343 (14)−0.0076 (15)−0.0065 (14)−0.0086 (12)
C260.0418 (17)0.0542 (19)0.0431 (16)−0.0059 (16)−0.0066 (14)0.0004 (14)
C270.0400 (16)0.0384 (16)0.0425 (15)0.0029 (13)0.0002 (13)−0.0008 (12)
C280.0571 (19)0.0471 (18)0.0580 (18)0.0050 (16)0.0054 (16)−0.0155 (15)

Geometric parameters (Å, °)

S1—C11.688 (2)C11—H110.9500
S2—C151.692 (2)C12—C131.392 (3)
N1—C11.331 (3)C12—H120.9500
N1—C21.473 (3)C13—H130.9500
N1—H1N0.8800C14—H14A0.9800
N2—C11.373 (3)C14—H14B0.9800
N2—C41.425 (3)C14—H14C0.9800
N2—C81.443 (3)C16—C171.487 (4)
N3—C151.329 (3)C16—C201.520 (4)
N3—C161.478 (3)C16—C191.531 (4)
N3—H3N0.8800C17—C181.324 (4)
N4—C151.366 (3)C17—H170.9500
N4—C181.426 (3)C18—C211.484 (4)
N4—C221.450 (3)C19—H19A0.9800
C2—C31.487 (3)C19—H19B0.9800
C2—C51.521 (3)C19—H19C0.9800
C2—C61.521 (3)C20—H20A0.9800
C3—C41.329 (3)C20—H20B0.9800
C3—H30.9500C20—H20C0.9800
C4—C71.493 (3)C21—H21A0.9800
C5—H5A0.9800C21—H21B0.9800
C5—H5B0.9800C21—H21C0.9800
C5—H5C0.9800C22—C231.372 (3)
C6—H6A0.9800C22—C271.381 (3)
C6—H6B0.9800C23—C241.396 (3)
C6—H6C0.9800C23—H230.9500
C7—H7A0.9800C24—C251.382 (4)
C7—H7B0.9800C24—C281.501 (4)
C7—H7C0.9800C25—C261.381 (4)
C8—C91.376 (3)C25—H250.9500
C8—C131.381 (3)C26—C271.386 (4)
C9—C101.396 (3)C26—H260.9500
C9—H90.9500C27—H270.9500
C10—C111.382 (4)C28—H28A0.9800
C10—C141.501 (3)C28—H28B0.9800
C11—C121.380 (3)C28—H28C0.9800
C1—N1—C2126.47 (19)C10—C14—H14A109.5
C1—N1—H1N116.8C10—C14—H14B109.5
C2—N1—H1N116.8H14A—C14—H14B109.5
C1—N2—C4121.07 (19)C10—C14—H14C109.5
C1—N2—C8118.86 (19)H14A—C14—H14C109.5
C4—N2—C8119.99 (18)H14B—C14—H14C109.5
C15—N3—C16128.0 (2)N3—C15—N4117.6 (2)
C15—N3—H3N116.0N3—C15—S2120.77 (18)
C16—N3—H3N116.0N4—C15—S2121.60 (18)
C15—N4—C18120.7 (2)N3—C16—C17107.7 (2)
C15—N4—C22120.1 (2)N3—C16—C20108.3 (2)
C18—N4—C22119.22 (19)C17—C16—C20112.2 (2)
N1—C1—N2117.0 (2)N3—C16—C19109.3 (2)
N1—C1—S1121.21 (17)C17—C16—C19110.0 (2)
N2—C1—S1121.80 (17)C20—C16—C19109.3 (2)
N1—C2—C3107.76 (19)C18—C17—C16124.3 (2)
N1—C2—C5107.5 (2)C18—C17—H17117.9
C3—C2—C5112.3 (2)C16—C17—H17117.9
N1—C2—C6108.8 (2)C17—C18—N4120.0 (2)
C3—C2—C6110.9 (2)C17—C18—C21123.5 (3)
C5—C2—C6109.4 (2)N4—C18—C21116.6 (2)
C4—C3—C2123.1 (2)C16—C19—H19A109.5
C4—C3—H3118.4C16—C19—H19B109.5
C2—C3—H3118.4H19A—C19—H19B109.5
C3—C4—N2119.3 (2)C16—C19—H19C109.5
C3—C4—C7124.2 (2)H19A—C19—H19C109.5
N2—C4—C7116.5 (2)H19B—C19—H19C109.5
C2—C5—H5A109.5C16—C20—H20A109.5
C2—C5—H5B109.5C16—C20—H20B109.5
H5A—C5—H5B109.5H20A—C20—H20B109.5
C2—C5—H5C109.5C16—C20—H20C109.5
H5A—C5—H5C109.5H20A—C20—H20C109.5
H5B—C5—H5C109.5H20B—C20—H20C109.5
C2—C6—H6A109.5C18—C21—H21A109.5
C2—C6—H6B109.5C18—C21—H21B109.5
H6A—C6—H6B109.5H21A—C21—H21B109.5
C2—C6—H6C109.5C18—C21—H21C109.5
H6A—C6—H6C109.5H21A—C21—H21C109.5
H6B—C6—H6C109.5H21B—C21—H21C109.5
C4—C7—H7A109.5C23—C22—C27120.9 (2)
C4—C7—H7B109.5C23—C22—N4119.8 (2)
H7A—C7—H7B109.5C27—C22—N4119.2 (2)
C4—C7—H7C109.5C22—C23—C24120.6 (2)
H7A—C7—H7C109.5C22—C23—H23119.7
H7B—C7—H7C109.5C24—C23—H23119.7
C9—C8—C13121.5 (2)C25—C24—C23118.1 (2)
C9—C8—N2119.4 (2)C25—C24—C28121.6 (2)
C13—C8—N2119.2 (2)C23—C24—C28120.3 (2)
C8—C9—C10120.1 (2)C26—C25—C24121.3 (2)
C8—C9—H9119.9C26—C25—H25119.3
C10—C9—H9119.9C24—C25—H25119.3
C11—C10—C9118.3 (2)C25—C26—C27120.0 (3)
C11—C10—C14122.4 (2)C25—C26—H26120.0
C9—C10—C14119.3 (2)C27—C26—H26120.0
C12—C11—C10121.6 (2)C22—C27—C26119.0 (3)
C12—C11—H11119.2C22—C27—H27120.5
C10—C11—H11119.2C26—C27—H27120.5
C11—C12—C13119.9 (2)C24—C28—H28A109.5
C11—C12—H12120.1C24—C28—H28B109.5
C13—C12—H12120.1H28A—C28—H28B109.5
C8—C13—C12118.7 (2)C24—C28—H28C109.5
C8—C13—H13120.7H28A—C28—H28C109.5
C12—C13—H13120.7H28B—C28—H28C109.5
C2—N1—C1—N2−12.6 (4)C16—N3—C15—N4−5.1 (4)
C2—N1—C1—S1168.88 (18)C16—N3—C15—S2176.2 (2)
C4—N2—C1—N1−7.6 (3)C18—N4—C15—N3−6.2 (4)
C8—N2—C1—N1175.5 (2)C22—N4—C15—N3172.5 (2)
C4—N2—C1—S1170.90 (17)C18—N4—C15—S2172.50 (19)
C8—N2—C1—S1−6.0 (3)C22—N4—C15—S2−8.8 (3)
C1—N1—C2—C325.6 (3)C15—N3—C16—C1713.6 (4)
C1—N1—C2—C5146.8 (2)C15—N3—C16—C20135.1 (3)
C1—N1—C2—C6−94.7 (3)C15—N3—C16—C19−105.9 (3)
N1—C2—C3—C4−21.0 (3)N3—C16—C17—C18−12.5 (4)
C5—C2—C3—C4−139.2 (3)C20—C16—C17—C18−131.6 (3)
C6—C2—C3—C498.0 (3)C19—C16—C17—C18106.6 (3)
C2—C3—C4—N25.3 (4)C16—C17—C18—N43.8 (5)
C2—C3—C4—C7−175.9 (2)C16—C17—C18—C21−176.6 (3)
C1—N2—C4—C311.0 (3)C15—N4—C18—C176.8 (4)
C8—N2—C4—C3−172.1 (2)C22—N4—C18—C17−171.9 (3)
C1—N2—C4—C7−167.8 (2)C15—N4—C18—C21−172.8 (3)
C8—N2—C4—C79.1 (3)C22—N4—C18—C218.5 (4)
C1—N2—C8—C994.8 (3)C15—N4—C22—C23100.7 (3)
C4—N2—C8—C9−82.2 (3)C18—N4—C22—C23−80.6 (3)
C1—N2—C8—C13−85.9 (3)C15—N4—C22—C27−83.1 (3)
C4—N2—C8—C1397.1 (3)C18—N4—C22—C2795.6 (3)
C13—C8—C9—C100.1 (4)C27—C22—C23—C24−0.2 (4)
N2—C8—C9—C10179.3 (2)N4—C22—C23—C24175.8 (2)
C8—C9—C10—C111.4 (3)C22—C23—C24—C250.2 (4)
C8—C9—C10—C14−177.9 (2)C22—C23—C24—C28−179.5 (2)
C9—C10—C11—C12−1.8 (4)C23—C24—C25—C260.4 (4)
C14—C10—C11—C12177.4 (2)C28—C24—C25—C26−179.9 (3)
C10—C11—C12—C130.8 (4)C24—C25—C26—C27−0.9 (4)
C9—C8—C13—C12−1.2 (4)C23—C22—C27—C26−0.2 (4)
N2—C8—C13—C12179.5 (2)N4—C22—C27—C26−176.4 (2)
C11—C12—C13—C80.8 (3)C25—C26—C27—C220.8 (4)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N1—H1N···S20.882.623.419 (2)151
N3—H3N···S10.882.603.447 (2)163

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: ZS2028).

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