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The mol­ecule of the title compound, C28H24N2S2, has a crystallographically imposed center of symmetry at the mid-point of the N-N bond. It is not planar, due to the steric repulsion between S and H atoms.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806012396/hk2024sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806012396/hk2024Isup2.hkl
Contains datablock I

CCDC reference: 608352

Key indicators

  • Single-crystal X-ray study
  • T = 297 K
  • Mean [sigma](C-C)= 0.002 Å
  • R factor = 0.034
  • wR factor = 0.101
  • Data-to-parameter ratio = 18.8

checkCIF/PLATON results

No syntax errors found


No errors found in this datablock

Computing details top

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: DIRDIF99 (Beurskens et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

2-(Benzylsulfanyl)benzaldehyde azine top
Crystal data top
C28H24N2S2Z = 1
Mr = 452.61F(000) = 238
Triclinic, P1Dx = 1.261 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.5712 (5) ÅCell parameters from 25 reflections
b = 7.8467 (6) Åθ = 5.7–13.8°
c = 11.3069 (10) ŵ = 0.24 mm1
α = 91.882 (8)°T = 297 K
β = 92.124 (7)°Plate, yellow
γ = 117.234 (6)°0.59 × 0.41 × 0.25 mm
V = 595.92 (9) Å3
Data collection top
Enraf–Nonius CAD-4
diffractometer
2134 reflections with I > 2σ(I)
non–profiled ω/2θ scansRint = 0.008
Absorption correction: ψ scan
'North et al. (1968)'
θmax = 27.5°, θmin = 1.8°
Tmin = 0.907, Tmax = 0.938h = 99
2873 measured reflectionsk = 1010
2733 independent reflectionsl = 014
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.034 w = 1/[σ2(Fo2) + (0.0469P)2 + 0.0834P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.101(Δ/σ)max < 0.001
S = 1.05Δρmax = 0.17 e Å3
2733 reflectionsΔρmin = 0.18 e Å3
145 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.2146 (3)0.1074 (2)0.49801 (15)0.0730 (4)
H10.1520.22280.54320.088*
C20.2514 (3)0.0625 (3)0.54963 (17)0.0829 (5)
H20.2130.06020.6290.099*
C30.3433 (3)0.2324 (3)0.48488 (18)0.0783 (5)
H30.36640.34610.51950.094*
C40.4018 (3)0.2357 (3)0.36874 (18)0.0806 (5)
H40.46740.35220.32490.097*
C50.3640 (3)0.0669 (3)0.31615 (16)0.0749 (4)
H50.40240.07040.23670.09*
C60.2693 (2)0.1074 (2)0.38073 (13)0.0599 (4)
C70.2170 (2)0.2940 (2)0.32384 (16)0.0698 (4)
H7A0.21310.38990.38170.084*
H7B0.31430.27640.26020.084*
C100.0723 (2)0.57166 (19)0.18584 (12)0.0527 (3)
C110.0214 (2)0.6861 (2)0.20753 (14)0.0649 (4)
H110.11870.65040.26250.078*
C120.0291 (3)0.8518 (2)0.14820 (15)0.0717 (4)
H120.03420.92680.16390.086*
C130.1723 (3)0.9068 (2)0.06597 (15)0.0713 (4)
H130.2071.01940.0270.086*
C140.2635 (2)0.7941 (2)0.04189 (13)0.0613 (4)
H140.35880.83070.01450.074*
C150.2160 (2)0.62545 (18)0.10053 (12)0.0511 (3)
C160.3145 (2)0.50771 (19)0.07124 (12)0.0552 (3)
H160.26430.38440.09830.066*
N0.46620 (19)0.56947 (16)0.01011 (12)0.0647 (3)
S0.02599 (6)0.36762 (6)0.26657 (4)0.06888 (16)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0717 (10)0.0646 (9)0.0656 (10)0.0162 (8)0.0101 (8)0.0025 (7)
C20.0832 (12)0.0822 (12)0.0672 (10)0.0233 (10)0.0051 (9)0.0163 (9)
C30.0670 (10)0.0648 (10)0.0932 (13)0.0198 (8)0.0151 (9)0.0216 (9)
C40.0698 (11)0.0630 (10)0.0907 (13)0.0153 (8)0.0051 (9)0.0022 (9)
C50.0668 (10)0.0785 (11)0.0662 (10)0.0221 (8)0.0021 (8)0.0046 (8)
C60.0460 (7)0.0647 (9)0.0650 (9)0.0207 (6)0.0152 (6)0.0097 (7)
C70.0593 (9)0.0729 (10)0.0809 (11)0.0315 (8)0.0193 (8)0.0179 (8)
C100.0555 (7)0.0511 (7)0.0513 (7)0.0244 (6)0.0014 (6)0.0049 (5)
C110.0744 (10)0.0720 (9)0.0600 (8)0.0434 (8)0.0071 (7)0.0057 (7)
C120.0896 (12)0.0716 (10)0.0711 (10)0.0525 (9)0.0044 (8)0.0031 (8)
C130.0882 (11)0.0569 (9)0.0721 (10)0.0362 (8)0.0044 (9)0.0135 (7)
C140.0672 (9)0.0524 (8)0.0588 (8)0.0224 (7)0.0030 (7)0.0109 (6)
C150.0525 (7)0.0442 (6)0.0509 (7)0.0173 (6)0.0012 (5)0.0038 (5)
C160.0575 (8)0.0426 (6)0.0602 (8)0.0174 (6)0.0123 (6)0.0091 (5)
N0.0653 (7)0.0487 (6)0.0809 (8)0.0246 (6)0.0251 (6)0.0160 (6)
S0.0663 (2)0.0705 (3)0.0822 (3)0.0385 (2)0.02925 (19)0.0333 (2)
Geometric parameters (Å, º) top
C1—C61.375 (2)C10—C111.396 (2)
C1—C21.385 (2)C10—C151.4059 (19)
C1—H10.93C10—S1.7680 (14)
C2—C31.359 (3)C11—C121.381 (2)
C2—H20.93C11—H110.93
C3—C41.366 (3)C12—C131.378 (3)
C3—H30.93C12—H120.93
C4—C51.380 (2)C13—C141.375 (2)
C4—H40.93C13—H130.93
C5—C61.384 (2)C14—C151.3999 (18)
C5—H50.93C14—H140.93
C6—C71.505 (2)C15—C161.466 (2)
C7—S1.8103 (15)C16—N1.2662 (18)
C7—H7A0.97C16—H160.93
C7—H7B0.97N—Ni1.416 (2)
C6—C1—C2120.79 (16)C11—C10—C15118.92 (13)
C6—C1—H1119.6C11—C10—S122.53 (11)
C2—C1—H1119.6C15—C10—S118.48 (10)
C3—C2—C1120.32 (18)C12—C11—C10120.72 (15)
C3—C2—H2119.8C12—C11—H11119.6
C1—C2—H2119.8C10—C11—H11119.6
C2—C3—C4119.75 (17)C13—C12—C11120.56 (15)
C2—C3—H3120.1C13—C12—H12119.7
C4—C3—H3120.1C11—C12—H12119.7
C3—C4—C5120.35 (17)C14—C13—C12119.54 (14)
C3—C4—H4119.8C14—C13—H13120.2
C5—C4—H4119.8C12—C13—H13120.2
C4—C5—C6120.56 (17)C13—C14—C15121.32 (15)
C4—C5—H5119.7C13—C14—H14119.3
C6—C5—H5119.7C15—C14—H14119.3
C1—C6—C5118.20 (15)C14—C15—C10118.93 (13)
C1—C6—C7120.19 (15)C14—C15—C16119.71 (13)
C5—C6—C7121.53 (15)C10—C15—C16121.36 (12)
C6—C7—S105.99 (10)N—C16—C15121.71 (12)
C6—C7—H7A110.5N—C16—H16119.1
S—C7—H7A110.5C15—C16—H16119.1
C6—C7—H7B110.5C16—N—Ni112.24 (14)
S—C7—H7B110.5C10—S—C7105.25 (7)
H7A—C7—H7B108.7
C6—C1—C2—C30.3 (3)C12—C13—C14—C150.9 (2)
C1—C2—C3—C40.8 (3)C13—C14—C15—C100.2 (2)
C2—C3—C4—C51.5 (3)C13—C14—C15—C16179.15 (14)
C3—C4—C5—C61.0 (3)C11—C10—C15—C141.3 (2)
C2—C1—C6—C50.7 (2)S—C10—C15—C14175.67 (10)
C2—C1—C6—C7176.18 (16)C11—C10—C15—C16178.00 (13)
C4—C5—C6—C10.0 (2)S—C10—C15—C165.00 (18)
C4—C5—C6—C7176.78 (16)C14—C15—C16—N12.7 (2)
C1—C6—C7—S89.07 (16)C10—C15—C16—N167.96 (14)
C5—C6—C7—S87.67 (16)C15—C16—N—Ni178.43 (15)
C15—C10—C11—C121.4 (2)C11—C10—S—C723.22 (15)
S—C10—C11—C12175.47 (12)C15—C10—S—C7159.90 (12)
C10—C11—C12—C130.3 (3)C6—C7—S—C10173.57 (11)
C11—C12—C13—C140.9 (3)
Symmetry code: (i) x+1, y+1, z.
 

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