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Acta Crystallogr Sect E Struct Rep Online. 2010 December 1; 66(Pt 12): o3307.
Published online 2010 November 27. doi:  10.1107/S160053681004821X
PMCID: PMC3011374

N,N′-Bis(3-phenyl­prop-2-en-1-yl­idene)-2,2′-disulfanediyldianiline

Abstract

In the title compound, C30H24N2S2, the two phenyl rings attached to the S atoms are oriented nearly perpendicularly, making a dihedral angle of 86.14 (8)°. Each of the two ArCH=CHCH=N units is almost planar, having maximum deviations from the least-squares planes of 0.125 and 0.149 Å, and rotated around the C—N bonds relative to the adjacent phenyl ring by 110.26 and 30.30°.

Related literature

The structure of the title compound was determined within a project on the synthesis of new ligands based on diaryl­disulfides, see: Bhowon et al. (2001 [triangle], 2005 [triangle], 2007 [triangle]); Raftery et al. (2009 [triangle]).

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Object name is e-66-o3307-scheme1.jpg

Experimental

Crystal data

  • C30H24N2S2
  • M r = 476.63
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-o3307-efi1.jpg
  • a = 20.2393 (13) Å
  • b = 9.1593 (6) Å
  • c = 13.5335 (8) Å
  • β = 104.995 (1)°
  • V = 2423.4 (3) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.24 mm−1
  • T = 100 K
  • 0.35 × 0.31 × 0.30 mm

Data collection

  • Bruker SMART CCD area-detector diffractometer
  • 20381 measured reflections
  • 5736 independent reflections
  • 4962 reflections with I > 2σ(I)
  • R int = 0.041

Refinement

  • R[F 2 > 2σ(F 2)] = 0.047
  • wR(F 2) = 0.112
  • S = 1.08
  • 5736 reflections
  • 307 parameters
  • H-atom parameters constrained
  • Δρmax = 0.48 e Å−3
  • Δρmin = −0.22 e Å−3

Data collection: SMART (Bruker, 2007 [triangle]); cell refinement: SAINT-Plus (Bruker, 2007 [triangle]); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053681004821X/nc2202sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681004821X/nc2202Isup2.hkl

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

supplementary crystallographic information

Comment

The structure of the title compound was determined within a project on the synthesis of new ligands based on diaryldisulfides (Bhowon et al., 2001; Bhowon et al. 2005; Bhowon et al., 2007; Raftery et al. 2009). In this project we have synthesized 2,2'-dithiobis[N-(3-phenyl- 2-propen-1-ylidene) benzenamine via the condensation of 2,2'-dithiobis(benzenamine) with cinnamaldehyde. The structure determination revealed that each of the ArCH=CHCH=N moieties are coplanar but rotated relative to the adjacent phenyl rings. Moreover, the phenyl rings attached to the sulfur atom are twisted around the sulfur-sulfur single bond so that they are nearly perpendicularly oriented.

Experimental

2,2'-Dithiobis(benzenamine)(0.49 g, 2 mmol) was added to a solution of trans cinnamaldehyde (0.50 mL, 4 mmol) in ethanol (20 ml) and the mixture was heated at reflux for 3 h. On evaporation in vacuo, a yellow crude product was obtained which was recrystallised from CHCl3/Et2O to yield the bis-imine (86 percent) as yellow crystals, mp 435 K. I.R. 1624, 1609 cm-1; 1H-NMR (250 MHz, DMSO-d6) 8.33 (1H, d, 3 Hz), 8.31 (1H, d, 3 Hz), 7.66 (2H, dd, 4.5, 3 Hz), 7.59-7.62 (4H, m), 7.26-7.16 (2H, m), 7.05 (2H, dd, 4.5, 3 Hz). 13C-NMR (62.5 MHz, DMSO-d6) 163.1, 152.8, 148.8, 131.6, 129.8, 129.1, 129.0, 128.5, 128.0, 76.5. Anal. Calc. (Found) C, 75.4 (75.1), H, 5.0 (5.0), N, 5.9 (6.0), S, 13.9 (14.0).

Refinement

H atoms were included in calculated positions with C—H distances of 0.95(CH), 0.99(CH2) & 0.98(CH3)Å; Uĩso(H) values were fixed at 1.2Ueq(C) except for CH3 where Uĩso(H) values of 1.5Ueq(C) were used.

Figures

Fig. 1.
Crystal structure of the title compound with labelling and displacement elliposids drawn at the 50% probability level.

Crystal data

C30H24N2S2Dx = 1.306 Mg m3
Mr = 476.63Melting point: 435 K
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 20.2393 (13) ÅCell parameters from 6928 reflections
b = 9.1593 (6) Åθ = 2.5–28.3°
c = 13.5335 (8) ŵ = 0.24 mm1
β = 104.995 (1)°T = 100 K
V = 2423.4 (3) Å3Block, yellow
Z = 40.35 × 0.31 × 0.30 mm
F(000) = 1000

Data collection

Bruker SMART CCD area-detector diffractometer4962 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.041
graphiteθmax = 28.3°, θmin = 2.1°
phi and ω scansh = −26→26
20381 measured reflectionsk = −12→12
5736 independent reflectionsl = −17→17

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)] = 0.047Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.112H-atom parameters constrained
S = 1.08w = 1/[σ2(Fo2) + (0.0595P)2 + 0.2559P] where P = (Fo2 + 2Fc2)/3
5736 reflections(Δ/σ)max = 0.001
307 parametersΔρmax = 0.48 e Å3
0 restraintsΔρmin = −0.22 e Å3

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
C10.38459 (8)1.25065 (18)0.51729 (12)0.0195 (3)
C20.31992 (8)1.18586 (17)0.48098 (12)0.0180 (3)
C30.26430 (9)1.23904 (19)0.51183 (13)0.0220 (3)
H30.22061.19510.48750.026*
C40.27272 (9)1.3567 (2)0.57839 (13)0.0258 (4)
H40.23471.39290.59980.031*
C50.33636 (10)1.4218 (2)0.61399 (13)0.0275 (4)
H50.34161.50290.65920.033*
C60.39234 (9)1.36868 (19)0.58369 (13)0.0241 (4)
H60.43591.41310.60840.029*
C70.46740 (8)1.24584 (19)0.42592 (13)0.0225 (4)
H70.45391.34240.40400.027*
C80.51906 (8)1.17317 (19)0.38739 (13)0.0227 (4)
H80.53951.08630.41980.027*
C90.53883 (8)1.22549 (19)0.30712 (13)0.0236 (4)
H90.52021.31700.28090.028*
C100.58617 (8)1.15668 (19)0.25538 (12)0.0210 (3)
C110.61820 (9)1.02313 (19)0.28774 (13)0.0227 (4)
H110.60850.97330.34390.027*
C120.66411 (9)0.9628 (2)0.23856 (14)0.0266 (4)
H120.68640.87340.26220.032*
C130.67738 (9)1.03311 (19)0.15495 (14)0.0252 (4)
H130.70870.99200.12130.030*
C140.64471 (9)1.1634 (2)0.12084 (13)0.0251 (4)
H140.65321.21080.06290.030*
C150.59981 (9)1.22491 (19)0.17048 (13)0.0235 (4)
H150.57801.31470.14660.028*
C160.20139 (8)0.85527 (17)0.43037 (12)0.0177 (3)
C170.13867 (8)0.78088 (17)0.39865 (12)0.0184 (3)
C180.11973 (8)0.68668 (18)0.46757 (13)0.0221 (4)
H180.07780.63460.44710.026*
C190.16135 (9)0.66819 (19)0.56546 (13)0.0219 (3)
H190.14760.60460.61190.026*
C200.22306 (8)0.74204 (18)0.59609 (13)0.0209 (3)
H200.25150.72930.66340.025*
C210.24311 (8)0.83474 (18)0.52809 (12)0.0198 (3)
H210.28570.88440.54870.024*
C220.05392 (8)0.72355 (18)0.24995 (13)0.0205 (3)
H220.04940.63130.27960.025*
C230.01189 (8)0.75679 (18)0.14901 (13)0.0208 (3)
H230.01350.85260.12290.025*
C24−0.02929 (8)0.65861 (19)0.09061 (12)0.0204 (3)
H24−0.03400.56760.12170.025*
C25−0.06781 (8)0.67666 (18)−0.01621 (12)0.0186 (3)
C26−0.10459 (8)0.55894 (18)−0.06838 (13)0.0211 (3)
H26−0.10600.4698−0.03310.025*
C27−0.13915 (9)0.56984 (19)−0.17104 (13)0.0237 (4)
H27−0.16470.4892−0.20510.028*
C28−0.13637 (9)0.69832 (19)−0.22380 (13)0.0238 (4)
H28−0.15920.7054−0.29440.029*
C29−0.09991 (8)0.81704 (19)−0.17271 (13)0.0226 (4)
H29−0.09790.9053−0.20870.027*
C30−0.06685 (8)0.80699 (18)−0.07039 (13)0.0208 (3)
H30−0.04310.8894−0.03600.025*
N10.43975 (7)1.18250 (16)0.48865 (11)0.0229 (3)
N20.09713 (7)0.81600 (15)0.30036 (10)0.0201 (3)
S10.31958 (2)1.03606 (5)0.39689 (3)0.02044 (11)
S20.22014 (2)0.97846 (5)0.33968 (3)0.02173 (11)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C10.0200 (8)0.0190 (8)0.0186 (8)0.0010 (6)0.0031 (6)0.0051 (6)
C20.0228 (8)0.0156 (8)0.0151 (7)−0.0010 (6)0.0043 (6)0.0017 (6)
C30.0215 (8)0.0226 (9)0.0225 (8)−0.0004 (7)0.0068 (7)0.0052 (7)
C40.0299 (9)0.0242 (9)0.0264 (9)0.0043 (7)0.0132 (7)0.0020 (7)
C50.0382 (10)0.0215 (9)0.0227 (9)−0.0001 (8)0.0078 (8)−0.0025 (7)
C60.0252 (9)0.0220 (9)0.0224 (9)−0.0041 (7)0.0012 (7)0.0004 (7)
C70.0190 (8)0.0228 (9)0.0228 (9)−0.0013 (6)0.0005 (6)0.0018 (7)
C80.0163 (8)0.0256 (9)0.0236 (9)−0.0007 (6)0.0004 (6)0.0026 (7)
C90.0207 (8)0.0242 (9)0.0234 (9)0.0006 (7)0.0011 (7)0.0019 (7)
C100.0166 (8)0.0241 (9)0.0192 (8)−0.0030 (6)−0.0009 (6)−0.0010 (7)
C110.0240 (9)0.0225 (9)0.0183 (8)−0.0016 (7)−0.0005 (6)0.0024 (7)
C120.0262 (9)0.0233 (9)0.0261 (9)0.0031 (7)−0.0010 (7)−0.0007 (7)
C130.0224 (9)0.0264 (9)0.0258 (9)−0.0007 (7)0.0042 (7)−0.0077 (7)
C140.0253 (9)0.0280 (9)0.0217 (9)−0.0050 (7)0.0053 (7)−0.0003 (7)
C150.0223 (9)0.0233 (9)0.0229 (9)0.0003 (7)0.0027 (7)0.0028 (7)
C160.0209 (8)0.0162 (8)0.0170 (8)0.0002 (6)0.0066 (6)0.0004 (6)
C170.0186 (8)0.0184 (8)0.0174 (8)0.0018 (6)0.0035 (6)−0.0013 (6)
C180.0194 (8)0.0218 (8)0.0250 (9)−0.0020 (6)0.0057 (7)−0.0005 (7)
C190.0235 (9)0.0213 (8)0.0218 (8)0.0008 (7)0.0073 (7)0.0044 (7)
C200.0220 (8)0.0224 (8)0.0166 (8)0.0053 (6)0.0016 (6)0.0018 (6)
C210.0185 (8)0.0198 (8)0.0202 (8)−0.0010 (6)0.0034 (6)−0.0021 (6)
C220.0210 (8)0.0211 (8)0.0204 (8)−0.0016 (6)0.0072 (7)0.0006 (7)
C230.0205 (8)0.0211 (8)0.0207 (8)−0.0008 (6)0.0051 (6)0.0006 (6)
C240.0199 (8)0.0221 (8)0.0194 (8)−0.0019 (6)0.0053 (6)0.0016 (6)
C250.0145 (7)0.0220 (8)0.0195 (8)−0.0002 (6)0.0049 (6)−0.0022 (6)
C260.0204 (8)0.0201 (8)0.0232 (8)−0.0021 (6)0.0061 (7)0.0015 (7)
C270.0226 (9)0.0235 (9)0.0233 (9)−0.0035 (7)0.0027 (7)−0.0047 (7)
C280.0218 (8)0.0289 (9)0.0185 (8)0.0022 (7)0.0011 (7)−0.0003 (7)
C290.0207 (8)0.0209 (8)0.0260 (9)0.0023 (6)0.0058 (7)0.0037 (7)
C300.0162 (8)0.0197 (8)0.0257 (9)−0.0016 (6)0.0037 (6)−0.0029 (7)
N10.0183 (7)0.0226 (7)0.0273 (8)−0.0009 (6)0.0051 (6)0.0010 (6)
N20.0190 (7)0.0222 (7)0.0184 (7)−0.0008 (5)0.0034 (5)−0.0001 (6)
S10.0206 (2)0.0211 (2)0.0203 (2)−0.00339 (15)0.00639 (16)−0.00296 (16)
S20.0230 (2)0.0238 (2)0.0160 (2)−0.00575 (16)0.00063 (16)0.00236 (16)

Geometric parameters (Å, °)

C1—C61.388 (2)C16—C171.406 (2)
C1—C21.405 (2)C16—S21.7790 (16)
C1—N11.418 (2)C17—C181.395 (2)
C2—C31.386 (2)C17—N21.415 (2)
C2—S11.7815 (16)C18—C191.384 (2)
C3—C41.386 (2)C18—H180.9500
C3—H30.9500C19—C201.386 (2)
C4—C51.388 (3)C19—H190.9500
C4—H40.9500C20—C211.388 (2)
C5—C61.389 (2)C20—H200.9500
C5—H50.9500C21—H210.9500
C6—H60.9500C22—N21.280 (2)
C7—N11.271 (2)C22—C231.443 (2)
C7—C81.446 (2)C22—H220.9500
C7—H70.9500C23—C241.337 (2)
C8—C91.340 (2)C23—H230.9500
C8—H80.9500C24—C251.463 (2)
C9—C101.467 (2)C24—H240.9500
C9—H90.9500C25—C261.394 (2)
C10—C151.397 (2)C25—C301.404 (2)
C10—C111.400 (2)C26—C271.388 (2)
C11—C121.390 (2)C26—H260.9500
C11—H110.9500C27—C281.385 (2)
C12—C131.387 (3)C27—H270.9500
C12—H120.9500C28—C291.393 (2)
C13—C141.384 (2)C28—H280.9500
C13—H130.9500C29—C301.376 (2)
C14—C151.382 (2)C29—H290.9500
C14—H140.9500C30—H300.9500
C15—H150.9500S1—S22.0302 (6)
C16—C211.386 (2)
C6—C1—C2119.62 (15)C17—C16—S2115.69 (12)
C6—C1—N1123.68 (15)C18—C17—C16118.56 (15)
C2—C1—N1116.53 (15)C18—C17—N2124.75 (15)
C3—C2—C1120.12 (15)C16—C17—N2116.54 (14)
C3—C2—S1126.42 (13)C19—C18—C17120.73 (15)
C1—C2—S1113.46 (12)C19—C18—H18119.6
C4—C3—C2119.72 (16)C17—C18—H18119.6
C4—C3—H3120.1C18—C19—C20120.31 (15)
C2—C3—H3120.1C18—C19—H19119.8
C3—C4—C5120.45 (16)C20—C19—H19119.8
C3—C4—H4119.8C19—C20—C21119.72 (15)
C5—C4—H4119.8C19—C20—H20120.1
C4—C5—C6120.11 (16)C21—C20—H20120.1
C4—C5—H5119.9C16—C21—C20120.36 (15)
C6—C5—H5119.9C16—C21—H21119.8
C1—C6—C5119.98 (16)C20—C21—H21119.8
C1—C6—H6120.0N2—C22—C23121.28 (15)
C5—C6—H6120.0N2—C22—H22119.4
N1—C7—C8121.00 (16)C23—C22—H22119.4
N1—C7—H7119.5C24—C23—C22122.86 (16)
C8—C7—H7119.5C24—C23—H23118.6
C9—C8—C7121.56 (16)C22—C23—H23118.6
C9—C8—H8119.2C23—C24—C25126.82 (16)
C7—C8—H8119.2C23—C24—H24116.6
C8—C9—C10127.03 (16)C25—C24—H24116.6
C8—C9—H9116.5C26—C25—C30118.10 (15)
C10—C9—H9116.5C26—C25—C24119.41 (15)
C15—C10—C11118.30 (16)C30—C25—C24122.43 (15)
C15—C10—C9119.53 (15)C27—C26—C25121.07 (16)
C11—C10—C9122.17 (15)C27—C26—H26119.5
C12—C11—C10120.67 (16)C25—C26—H26119.5
C12—C11—H11119.7C28—C27—C26119.99 (16)
C10—C11—H11119.7C28—C27—H27120.0
C13—C12—C11120.05 (16)C26—C27—H27120.0
C13—C12—H12120.0C27—C28—C29119.62 (16)
C11—C12—H12120.0C27—C28—H28120.2
C14—C13—C12119.71 (17)C29—C28—H28120.2
C14—C13—H13120.1C30—C29—C28120.28 (16)
C12—C13—H13120.1C30—C29—H29119.9
C15—C14—C13120.45 (16)C28—C29—H29119.9
C15—C14—H14119.8C29—C30—C25120.91 (15)
C13—C14—H14119.8C29—C30—H30119.5
C14—C15—C10120.80 (16)C25—C30—H30119.5
C14—C15—H15119.6C7—N1—C1119.70 (15)
C10—C15—H15119.6C22—N2—C17120.57 (14)
C21—C16—C17120.31 (14)C2—S1—S2106.46 (6)
C21—C16—S2123.95 (12)C16—S2—S1105.61 (6)
C6—C1—C2—C3−0.4 (2)C17—C18—C19—C20−0.8 (3)
N1—C1—C2—C3175.08 (15)C18—C19—C20—C21−0.1 (3)
C6—C1—C2—S1−179.93 (12)C17—C16—C21—C20−0.8 (2)
N1—C1—C2—S1−4.46 (19)S2—C16—C21—C20176.64 (12)
C1—C2—C3—C40.2 (2)C19—C20—C21—C160.9 (2)
S1—C2—C3—C4179.67 (13)N2—C22—C23—C24173.89 (16)
C2—C3—C4—C50.2 (3)C22—C23—C24—C25−172.68 (15)
C3—C4—C5—C6−0.5 (3)C23—C24—C25—C26175.30 (16)
C2—C1—C6—C50.1 (2)C23—C24—C25—C30−1.8 (3)
N1—C1—C6—C5−174.99 (16)C30—C25—C26—C270.2 (2)
C4—C5—C6—C10.3 (3)C24—C25—C26—C27−177.00 (15)
N1—C7—C8—C9166.62 (17)C25—C26—C27—C281.2 (3)
C7—C8—C9—C10−174.57 (16)C26—C27—C28—C29−1.3 (3)
C8—C9—C10—C15178.26 (17)C27—C28—C29—C30−0.1 (3)
C8—C9—C10—C11−1.3 (3)C28—C29—C30—C251.5 (2)
C15—C10—C11—C122.1 (2)C26—C25—C30—C29−1.6 (2)
C9—C10—C11—C12−178.36 (16)C24—C25—C30—C29175.55 (15)
C10—C11—C12—C13−1.6 (3)C8—C7—N1—C1−173.79 (15)
C11—C12—C13—C140.0 (3)C6—C1—N1—C7−74.5 (2)
C12—C13—C14—C151.0 (3)C2—C1—N1—C7110.26 (18)
C13—C14—C15—C10−0.5 (3)C23—C22—N2—C17−179.07 (15)
C11—C10—C15—C14−1.1 (2)C18—C17—N2—C22−30.3 (2)
C9—C10—C15—C14179.36 (15)C16—C17—N2—C22154.31 (15)
C21—C16—C17—C180.0 (2)C3—C2—S1—S28.01 (16)
S2—C16—C17—C18−177.67 (12)C1—C2—S1—S2−172.48 (10)
C21—C16—C17—N2175.68 (14)C21—C16—S2—S113.04 (15)
S2—C16—C17—N2−1.99 (19)C17—C16—S2—S1−169.38 (11)
C16—C17—C18—C190.8 (2)C2—S1—S2—C16−86.14 (8)
N2—C17—C18—C19−174.51 (15)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: NC2202).

References

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