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Acta Cryst. (2007). E63, o3307
https://doi.org/10.1107/S1600536807029984
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Bis{4-[(5-methyl­thien-2-yl)methyl­ene­amino]phen­yl} sulfide

Y.-F. Zheng, L.-G. Wang and C.-N. Zhang
In the title compound, C24H20N2S3, all geometric parameters are in the usual ranges. The two benzene rings are almost perpendicular [85.80 (11)°]. The dihedral angle between the benzene and thiophene rings are 45.16 (15) and 37.43 (14)° in the two halves. The C=N double bonds are coplanar with the thiophene rings.
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Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807029984/bt2400sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807029984/bt2400Isup2.hkl
Contains datablock I

CCDC reference: 655029

checkCIF report

Key indicators

  • Single-crystal X-ray study
  • T = 291 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.065
  • wR factor = 0.134
  • Data-to-parameter ratio = 16.2

checkCIF/PLATON results

No syntax errors found




Alert level C
CELLV02_ALERT_1_C  The supplied cell volume s.u. differs from that
            calculated from the cell parameter s.u.'s by > 2
            Calculated cell volume su =       7.19
            Cell volume su given      =      11.00
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent .....          ?
PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...          5


   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   3 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
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check
Comment top

Organosulfides are important intermediates in the field of medicinal chemistry and organic synthesis (Luly et al., 1987; Corey et al., 1980). Thiazole Schiff bases are also important lead compounds active against emergent and re-emergent human and cattle infectious diseases, such as AIDS, hepatitis B, hepatitis C, tuberculosis and bovine viral diarrhea, (Vicini et al., 2003). Recently, we have synthesized the title ligand, a new schiff base containing thiophen component.

All bond lengths and angles have normal values (Fig. 1), the bond length of C–N are 1.267 (4) Å and 1.271 (4) Å, respectively, blong to typical double bonds. The dihedral angle between the two phenyl rings is 85.80 (11)°.

Related literature top

For related literature, see: Corey et al. (1980); Luly et al. (1987); Vicini et al. (2003).

Experimental top

Under nitrogen, a mixture of 4,4'-thiodianiline (1.08 g, 5 mmol) and 5-methylthiophene-2-carbaldehyde (1.26 g, 10 mmol) in anhydrous ethanol (20 ml) was refluxed for 6 h, yielding a yellow precipitate. The product was collected by vacuum filtration and washed with ethanol. After being dried a yellow solid was obtained in yield 85% (1.84 g). Yellow single crystals suitable for X-ray analysis were grown by slow evaporation of anhydrous ethanol at room temperature.

Refinement top

H atoms bonded to C atoms were positioned geometrically and refined using a riding model (including free rotation about the methyl C—C bond), with C—H = 0.93–0.96 Å and with Uiso(H) = 1.2(1.5 for methyl groups) times Ueq(C).

Structure description top

Organosulfides are important intermediates in the field of medicinal chemistry and organic synthesis (Luly et al., 1987; Corey et al., 1980). Thiazole Schiff bases are also important lead compounds active against emergent and re-emergent human and cattle infectious diseases, such as AIDS, hepatitis B, hepatitis C, tuberculosis and bovine viral diarrhea, (Vicini et al., 2003). Recently, we have synthesized the title ligand, a new schiff base containing thiophen component.

All bond lengths and angles have normal values (Fig. 1), the bond length of C–N are 1.267 (4) Å and 1.271 (4) Å, respectively, blong to typical double bonds. The dihedral angle between the two phenyl rings is 85.80 (11)°.

For related literature, see: Corey et al. (1980); Luly et al. (1987); Vicini et al. (2003).

Computing details top

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

Figures top
[Figure 1] Fig. 1. The molecular structure of (I), with atom labels and 30% probability displacement ellipsoids for non-H atoms.
Bis{4-[(5-methylthien-2-yl)methyleneamino]phenyl} sulfide top
Crystal data top
C24H20N2S3Z = 2
Mr = 432.60F(000) = 452
Triclinic, P1Dx = 1.321 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 5.315 (3) ÅCell parameters from 2294 reflections
b = 14.275 (4) Åθ = 2.3–25.5°
c = 15.106 (3) ŵ = 0.35 mm−1
α = 72.828 (3)°T = 291 K
β = 88.344 (4)°Block, yellow
γ = 83.314 (4)°0.30 × 0.24 × 0.22 mm
V = 1087.6 (11) Å3
Data collection top
Bruker SMART APEX CCD
diffractometer		4283 independent reflections
Radiation source: sealed tube3075 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.053
φ and ω scansθmax = 26.0°, θmin = 1.4°
Absorption correction: multi-scan
(SADABS; Bruker, 2000)		h = −6→6
Tmin = 0.901, Tmax = 0.926k = −17→17
11209 measured reflectionsl = −18→18
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)] = 0.065Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.134H-atom parameters constrained
S = 1.06 w = 1/[σ2(Fo2) + (0.04P)2 + 0.55P]
where P = (Fo2 + 2Fc2)/3
4283 reflections(Δ/σ)max < 0.001
264 parametersΔρmax = 0.21 e Å−3
0 restraintsΔρmin = −0.34 e Å−3
Crystal data top
C24H20N2S3γ = 83.314 (4)°
Mr = 432.60V = 1087.6 (11) Å3
Triclinic, P1Z = 2
a = 5.315 (3) ÅMo Kα radiation
b = 14.275 (4) ŵ = 0.35 mm−1
c = 15.106 (3) ÅT = 291 K
α = 72.828 (3)°0.30 × 0.24 × 0.22 mm
β = 88.344 (4)°
Data collection top
Bruker SMART APEX CCD
diffractometer		4283 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2000)		3075 reflections with I > 2σ(I)
Tmin = 0.901, Tmax = 0.926Rint = 0.053
11209 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0650 restraints
wR(F2) = 0.134H-atom parameters constrained
S = 1.06Δρmax = 0.21 e Å−3
4283 reflectionsΔρmin = −0.34 e Å−3
264 parameters
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.

Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)

3.9093 (0.0067) x - 7.3689 (0.0222) y + 2.0066 (0.0224) z = 2.2004 (0.0243)

* 0.0017 (0.0017) S1 * -0.0037 (0.0022) C2 * 0.0043 (0.0027) C3 * -0.0027 (0.0026) C4 * 0.0003 (0.0022) C5

Rms deviation of fitted atoms = 0.0029

3.1052 (0.0064) x + 0.2728 (0.0209) y + 11.7286 (0.0163) z = 12.8848 (0.0204)

Angle to previous plane (with approximate e.s.d.) = 45.16 (0.15)

* 0.0011 (0.0024) C7 * 0.0019 (0.0025) C8 * -0.0005 (0.0025) C9 * -0.0039 (0.0024) C10 * 0.0070 (0.0026) C11 * -0.0056 (0.0027) C12

Rms deviation of fitted atoms = 0.0041

3.5500 (0.0058) x + 8.3600 (0.0174) y - 5.2434 (0.0231) z = 7.6913 (0.0305)

Angle to previous plane (with approximate e.s.d.) = 85.80 (0.11)

* -0.0008 (0.0023) C13 * 0.0034 (0.0025) C14 * -0.0053 (0.0026) C15 * 0.0046 (0.0025) C16 * -0.0021 (0.0026) C17 * 0.0001 (0.0026) C18

Rms deviation of fitted atoms = 0.0033

3.7905 (0.0067) x + 11.0723 (0.0165) y + 4.4432 (0.0214) z = 17.2182 (0.0267)

Angle to previous plane (with approximate e.s.d.) = 37.43 (0.14)

* 0.0009 (0.0016) S3 * -0.0045 (0.0021) C20 * 0.0067 (0.0025) C21 * -0.0059 (0.0025) C22 * 0.0027 (0.0021) C23

Rms deviation of fitted atoms = 0.0046

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
C10.2614 (9)0.0886 (3)0.9139 (3)0.0857 (13)
H1A0.22400.03620.96740.129*
H1B0.37340.06220.87390.129*
H1C0.10710.11950.88110.129*
C20.3849 (7)0.1630 (2)0.9435 (3)0.0637 (10)
C30.3779 (8)0.1806 (3)1.0259 (3)0.0747 (11)
H30.28890.14601.07670.090*
C40.5197 (8)0.2571 (3)1.0272 (3)0.0675 (10)
H40.53180.27861.07920.081*
C50.6357 (7)0.2966 (2)0.9476 (2)0.0550 (8)
C60.7838 (7)0.3786 (2)0.9234 (2)0.0578 (8)
H60.80860.40970.96810.069*
C71.0027 (6)0.4972 (2)0.8216 (2)0.0483 (7)
C80.9070 (6)0.5813 (2)0.8451 (2)0.0558 (8)
H80.76530.57970.88280.067*
C91.0204 (6)0.6678 (2)0.8129 (2)0.0564 (8)
H90.95410.72360.82920.068*
C101.2311 (6)0.6715 (2)0.7567 (2)0.0431 (7)
C111.3271 (7)0.5885 (2)0.7341 (2)0.0562 (8)
H111.47090.58980.69740.067*
C121.2126 (7)0.5029 (2)0.7654 (3)0.0630 (9)
H121.27860.44770.74800.076*
C131.1345 (6)0.8760 (2)0.6981 (2)0.0467 (7)
C141.0991 (7)0.9302 (2)0.7597 (3)0.0594 (9)
H141.20800.91660.81010.071*
C150.8991 (7)1.0059 (2)0.7467 (3)0.0602 (9)
H150.87401.04180.78930.072*
C160.7382 (6)1.0280 (2)0.6711 (2)0.0486 (7)
C170.7769 (7)0.9728 (3)0.6105 (3)0.0618 (9)
H170.66910.98600.55980.074*
C180.9732 (7)0.8979 (2)0.6236 (2)0.0610 (9)
H180.99690.86160.58140.073*
C190.4707 (7)1.1612 (3)0.5835 (3)0.0599 (9)
H190.56241.15250.53260.072*
C200.2608 (6)1.2376 (2)0.5676 (2)0.0513 (8)
C210.1764 (8)1.3004 (3)0.4856 (2)0.0646 (10)
H210.24841.29980.42890.077*
C22−0.0331 (8)1.3671 (2)0.4953 (2)0.0645 (10)
H22−0.11501.41410.44520.077*
C23−0.1032 (6)1.3566 (2)0.5832 (2)0.0492 (7)
C24−0.3108 (7)1.4138 (3)0.6194 (2)0.0575 (8)
H24A−0.36121.47490.57280.086*
H24B−0.25281.42720.67350.086*
H24C−0.45271.37620.63520.086*
N10.8823 (6)0.41080 (19)0.84441 (19)0.0553 (7)
N20.5373 (5)1.10504 (19)0.6635 (2)0.0564 (7)
S10.5706 (2)0.23984 (7)0.86657 (6)0.0630 (3)
S21.38975 (16)0.77884 (6)0.71406 (6)0.0547 (2)
S30.08630 (18)1.26159 (7)0.65792 (6)0.0591 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.095 (3)0.063 (2)0.098 (3)−0.026 (2)−0.024 (3)−0.013 (2)
C20.065 (2)0.0417 (17)0.075 (3)−0.0114 (16)−0.0046 (18)−0.0008 (16)
C30.083 (3)0.069 (3)0.068 (3)−0.017 (2)0.020 (2)−0.013 (2)
C40.090 (3)0.061 (2)0.053 (2)−0.017 (2)0.0128 (19)−0.0194 (17)
C50.066 (2)0.0445 (17)0.0536 (19)−0.0078 (15)0.0000 (16)−0.0127 (14)
C60.063 (2)0.0511 (19)0.061 (2)−0.0100 (16)0.0017 (17)−0.0184 (16)
C70.0500 (18)0.0465 (17)0.0467 (17)−0.0004 (14)−0.0016 (14)−0.0130 (13)
C80.0474 (19)0.0500 (18)0.072 (2)−0.0072 (15)0.0172 (16)−0.0221 (16)
C90.053 (2)0.0464 (17)0.075 (2)−0.0053 (15)0.0135 (17)−0.0284 (16)
C100.0426 (16)0.0391 (15)0.0461 (16)0.0022 (12)0.0002 (12)−0.0128 (12)
C110.052 (2)0.0504 (18)0.067 (2)−0.0021 (15)0.0178 (16)−0.0223 (16)
C120.079 (3)0.0405 (17)0.071 (2)0.0017 (16)0.0194 (19)−0.0241 (16)
C130.0441 (17)0.0373 (15)0.0579 (19)−0.0071 (13)0.0091 (14)−0.0127 (13)
C140.062 (2)0.0539 (19)0.065 (2)−0.0011 (16)−0.0156 (17)−0.0224 (16)
C150.064 (2)0.057 (2)0.069 (2)−0.0027 (17)−0.0020 (18)−0.0341 (18)
C160.0406 (17)0.0417 (16)0.062 (2)−0.0036 (13)−0.0010 (14)−0.0136 (14)
C170.067 (2)0.057 (2)0.064 (2)0.0052 (17)−0.0145 (17)−0.0250 (17)
C180.075 (2)0.0487 (18)0.064 (2)0.0009 (17)−0.0018 (18)−0.0263 (16)
C190.059 (2)0.0530 (19)0.067 (2)−0.0016 (16)0.0128 (17)−0.0187 (17)
C200.0473 (18)0.0432 (16)0.062 (2)0.0014 (14)0.0112 (15)−0.0161 (15)
C210.085 (3)0.056 (2)0.0471 (19)0.0053 (18)0.0109 (18)−0.0122 (16)
C220.085 (3)0.0481 (19)0.0498 (19)0.0138 (18)0.0003 (18)−0.0065 (15)
C230.0559 (19)0.0396 (15)0.0518 (18)−0.0013 (14)0.0014 (14)−0.0147 (13)
C240.056 (2)0.059 (2)0.0521 (19)0.0071 (16)0.0073 (15)−0.0140 (15)
N10.0662 (18)0.0438 (14)0.0542 (16)−0.0097 (13)0.0059 (13)−0.0111 (12)
N20.0501 (16)0.0455 (15)0.0703 (19)0.0012 (12)0.0054 (14)−0.0150 (14)
S10.0819 (7)0.0545 (5)0.0542 (5)−0.0172 (4)0.0015 (4)−0.0150 (4)
S20.0445 (5)0.0455 (4)0.0723 (6)−0.0040 (3)0.0100 (4)−0.0156 (4)
S30.0609 (5)0.0588 (5)0.0509 (5)0.0044 (4)0.0039 (4)−0.0106 (4)
Geometric parameters (Å, º) top
C1—C21.489 (5)C13—C141.371 (4)
C1—H1A0.9600C13—C181.374 (5)
C1—H1B0.9600C13—S21.791 (3)
C1—H1C0.9600C14—C151.399 (5)
C2—C31.341 (5)C14—H140.9300
C2—S11.721 (4)C15—C161.385 (5)
C3—C41.402 (5)C15—H150.9300
C3—H30.9300C16—C171.370 (5)
C4—C51.334 (5)C16—N21.422 (4)
C4—H40.9300C17—C181.378 (5)
C5—C61.438 (5)C17—H170.9300
C5—S11.718 (3)C18—H180.9300
C6—N11.267 (4)C19—N21.271 (4)
C6—H60.9300C19—C201.439 (4)
C7—C121.378 (5)C19—H190.9300
C7—C81.386 (4)C20—C211.350 (5)
C7—N11.404 (4)C20—S31.722 (3)
C8—C91.387 (5)C21—C221.412 (5)
C8—H80.9300C21—H210.9300
C9—C101.382 (4)C22—C231.337 (5)
C9—H90.9300C22—H220.9300
C10—C111.367 (4)C23—C241.484 (4)
C10—S21.777 (3)C23—S31.725 (3)
C11—C121.379 (5)C24—H24A0.9600
C11—H110.9300C24—H24B0.9600
C12—H120.9300C24—H24C0.9600
C2—C1—H1A109.5C13—C14—C15120.0 (3)
C2—C1—H1B109.5C13—C14—H14120.0
H1A—C1—H1B109.5C15—C14—H14120.0
C2—C1—H1C109.5C16—C15—C14120.5 (3)
H1A—C1—H1C109.5C16—C15—H15119.7
H1B—C1—H1C109.5C14—C15—H15119.7
C3—C2—C1129.2 (4)C17—C16—C15118.5 (3)
C3—C2—S1111.1 (3)C17—C16—N2124.4 (3)
C1—C2—S1119.7 (3)C15—C16—N2117.1 (3)
C2—C3—C4112.4 (3)C16—C17—C18121.0 (3)
C2—C3—H3123.8C16—C17—H17119.5
C4—C3—H3123.8C18—C17—H17119.5
C5—C4—C3114.5 (4)C13—C18—C17120.8 (3)
C5—C4—H4122.7C13—C18—H18119.6
C3—C4—H4122.7C17—C18—H18119.6
C4—C5—C6129.1 (3)N2—C19—C20123.4 (3)
C4—C5—S1110.3 (3)N2—C19—H19118.3
C6—C5—S1120.5 (3)C20—C19—H19118.3
N1—C6—C5123.5 (3)C21—C20—C19127.5 (3)
N1—C6—H6118.3C21—C20—S3110.9 (2)
C5—C6—H6118.3C19—C20—S3121.5 (3)
C12—C7—C8117.7 (3)C20—C21—C22112.6 (3)
C12—C7—N1118.7 (3)C20—C21—H21123.7
C8—C7—N1123.3 (3)C22—C21—H21123.7
C7—C8—C9120.7 (3)C23—C22—C21114.0 (3)
C7—C8—H8119.6C23—C22—H22123.0
C9—C8—H8119.6C21—C22—H22123.0
C10—C9—C8120.4 (3)C22—C23—C24128.9 (3)
C10—C9—H9119.8C22—C23—S3110.6 (2)
C8—C9—H9119.8C24—C23—S3120.5 (2)
C11—C10—C9118.9 (3)C23—C24—H24A109.5
C11—C10—S2117.9 (2)C23—C24—H24B109.5
C9—C10—S2123.1 (2)H24A—C24—H24B109.5
C10—C11—C12120.6 (3)C23—C24—H24C109.5
C10—C11—H11119.7H24A—C24—H24C109.5
C12—C11—H11119.7H24B—C24—H24C109.5
C7—C12—C11121.6 (3)C6—N1—C7120.9 (3)
C7—C12—H12119.2C19—N2—C16118.8 (3)
C11—C12—H12119.2C5—S1—C291.71 (19)
C14—C13—C18119.2 (3)C10—S2—C13102.28 (15)
C14—C13—S2120.4 (3)C20—S3—C2391.82 (16)
C18—C13—S2120.4 (2)

Experimental details

Crystal data
Chemical formulaC24H20N2S3
Mr432.60
Crystal system, space groupTriclinic, P1
Temperature (K)291
a, b, c (Å)5.315 (3), 14.275 (4), 15.106 (3)
α, β, γ (°)72.828 (3), 88.344 (4), 83.314 (4)
V (Å3)1087.6 (11)
Z2
Radiation typeMo Kα
µ (mm−1)0.35
Crystal size (mm)0.30 × 0.24 × 0.22
Data collection
DiffractometerBruker SMART APEX CCD
Absorption correctionMulti-scan
(SADABS; Bruker, 2000)
Tmin, Tmax0.901, 0.926
No. of measured, independent and
observed [I > 2σ(I)] reflections		11209, 4283, 3075
Rint0.053
(sin θ/λ)max (Å−1)0.617
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.065, 0.134, 1.06
No. of reflections4283
No. of parameters264
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.21, −0.34

Computer programs: SMART (Bruker, 2000), SMART, SAINT (Bruker, 2000), SHELXTL (Bruker, 2000), SHELXTL.

 

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