2-(Benzyl­sulfan­yl)benzaldehyde azine

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.

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

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Computing details

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

Crystal data

C28H24N2S2	Z = 1
Mr = 452.61	F(000) = 238
Triclinic, P1	Dx = 1.261 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.5712 (5) Å	Cell parameters from 25 reflections
b = 7.8467 (6) Å	θ = 5.7–13.8°
c = 11.3069 (10) Å	µ = 0.24 mm^−1
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) Å^3

Data collection

Enraf–Nonius CAD-4 diffractometer	2134 reflections with I > 2σ(I)
non–profiled ω/2θ scans	Rint = 0.008
Absorption correction: ψ scan 'North et al. (1968)'	θmax = 27.5°, θmin = 1.8°
Tmin = 0.907, Tmax = 0.938	h = −9→9
2873 measured reflections	k = −10→10
2733 independent reflections	l = 0→14

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.034	w = 1/[σ^2(Fo^2) + (0.0469P)^2 + 0.0834P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.101	(Δ/σ)max < 0.001
S = 1.05	Δρmax = 0.17 e Å^−3
2733 reflections	Δρmin = −0.18 e Å^−3
145 parameters

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C1	−0.2146 (3)	0.1074 (2)	0.49801 (15)	0.0730 (4)
H1	−0.152	0.2228	0.5432	0.088*
C2	−0.2514 (3)	−0.0625 (3)	0.54963 (17)	0.0829 (5)
H2	−0.213	−0.0602	0.629	0.099*
C3	−0.3433 (3)	−0.2324 (3)	0.48488 (18)	0.0783 (5)
H3	−0.3664	−0.3461	0.5195	0.094*
C4	−0.4018 (3)	−0.2357 (3)	0.36874 (18)	0.0806 (5)
H4	−0.4674	−0.3522	0.3249	0.097*
C5	−0.3640 (3)	−0.0669 (3)	0.31615 (16)	0.0749 (4)
H5	−0.4024	−0.0704	0.2367	0.09*
C6	−0.2693 (2)	0.1074 (2)	0.38073 (13)	0.0599 (4)
C7	−0.2170 (2)	0.2940 (2)	0.32384 (16)	0.0698 (4)
H7A	−0.2131	0.3899	0.3817	0.084*
H7B	−0.3143	0.2764	0.2602	0.084*
C10	0.0723 (2)	0.57166 (19)	0.18584 (12)	0.0527 (3)
C11	−0.0214 (2)	0.6861 (2)	0.20753 (14)	0.0649 (4)
H11	−0.1187	0.6504	0.2625	0.078*
C12	0.0291 (3)	0.8518 (2)	0.14820 (15)	0.0717 (4)
H12	−0.0342	0.9268	0.1639	0.086*
C13	0.1723 (3)	0.9068 (2)	0.06597 (15)	0.0713 (4)
H13	0.207	1.0194	0.027	0.086*
C14	0.2635 (2)	0.7941 (2)	0.04189 (13)	0.0613 (4)
H14	0.3588	0.8307	−0.0145	0.074*
C15	0.2160 (2)	0.62545 (18)	0.10053 (12)	0.0511 (3)
C16	0.3145 (2)	0.50771 (19)	0.07124 (12)	0.0552 (3)
H16	0.2643	0.3844	0.0983	0.066*
N	0.46620 (19)	0.56947 (16)	0.01011 (12)	0.0647 (3)
S	0.02599 (6)	0.36762 (6)	0.26657 (4)	0.06888 (16)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0717 (10)	0.0646 (9)	0.0656 (10)	0.0162 (8)	0.0101 (8)	0.0025 (7)
C2	0.0832 (12)	0.0822 (12)	0.0672 (10)	0.0233 (10)	0.0051 (9)	0.0163 (9)
C3	0.0670 (10)	0.0648 (10)	0.0932 (13)	0.0198 (8)	0.0151 (9)	0.0216 (9)
C4	0.0698 (11)	0.0630 (10)	0.0907 (13)	0.0153 (8)	0.0051 (9)	−0.0022 (9)
C5	0.0668 (10)	0.0785 (11)	0.0662 (10)	0.0221 (8)	0.0021 (8)	0.0046 (8)
C6	0.0460 (7)	0.0647 (9)	0.0650 (9)	0.0207 (6)	0.0152 (6)	0.0097 (7)
C7	0.0593 (9)	0.0729 (10)	0.0809 (11)	0.0315 (8)	0.0193 (8)	0.0179 (8)
C10	0.0555 (7)	0.0511 (7)	0.0513 (7)	0.0244 (6)	0.0014 (6)	0.0049 (5)
C11	0.0744 (10)	0.0720 (9)	0.0600 (8)	0.0434 (8)	0.0071 (7)	0.0057 (7)
C12	0.0896 (12)	0.0716 (10)	0.0711 (10)	0.0525 (9)	−0.0044 (8)	0.0031 (8)
C13	0.0882 (11)	0.0569 (9)	0.0721 (10)	0.0362 (8)	−0.0044 (9)	0.0135 (7)
C14	0.0672 (9)	0.0524 (8)	0.0588 (8)	0.0224 (7)	0.0030 (7)	0.0109 (6)
C15	0.0525 (7)	0.0442 (6)	0.0509 (7)	0.0173 (6)	0.0012 (5)	0.0038 (5)
C16	0.0575 (8)	0.0426 (6)	0.0602 (8)	0.0174 (6)	0.0123 (6)	0.0091 (5)
N	0.0653 (7)	0.0487 (6)	0.0809 (8)	0.0246 (6)	0.0251 (6)	0.0160 (6)
S	0.0663 (2)	0.0705 (3)	0.0822 (3)	0.0385 (2)	0.02925 (19)	0.0333 (2)

Geometric parameters (Å, º)

C1—C6	1.375 (2)	C10—C11	1.396 (2)
C1—C2	1.385 (2)	C10—C15	1.4059 (19)
C1—H1	0.93	C10—S	1.7680 (14)
C2—C3	1.359 (3)	C11—C12	1.381 (2)
C2—H2	0.93	C11—H11	0.93
C3—C4	1.366 (3)	C12—C13	1.378 (3)
C3—H3	0.93	C12—H12	0.93
C4—C5	1.380 (2)	C13—C14	1.375 (2)
C4—H4	0.93	C13—H13	0.93
C5—C6	1.384 (2)	C14—C15	1.3999 (18)
C5—H5	0.93	C14—H14	0.93
C6—C7	1.505 (2)	C15—C16	1.466 (2)
C7—S	1.8103 (15)	C16—N	1.2662 (18)
C7—H7A	0.97	C16—H16	0.93
C7—H7B	0.97	N—N^i	1.416 (2)
C6—C1—C2	120.79 (16)	C11—C10—C15	118.92 (13)
C6—C1—H1	119.6	C11—C10—S	122.53 (11)
C2—C1—H1	119.6	C15—C10—S	118.48 (10)
C3—C2—C1	120.32 (18)	C12—C11—C10	120.72 (15)
C3—C2—H2	119.8	C12—C11—H11	119.6
C1—C2—H2	119.8	C10—C11—H11	119.6
C2—C3—C4	119.75 (17)	C13—C12—C11	120.56 (15)
C2—C3—H3	120.1	C13—C12—H12	119.7
C4—C3—H3	120.1	C11—C12—H12	119.7
C3—C4—C5	120.35 (17)	C14—C13—C12	119.54 (14)
C3—C4—H4	119.8	C14—C13—H13	120.2
C5—C4—H4	119.8	C12—C13—H13	120.2
C4—C5—C6	120.56 (17)	C13—C14—C15	121.32 (15)
C4—C5—H5	119.7	C13—C14—H14	119.3
C6—C5—H5	119.7	C15—C14—H14	119.3
C1—C6—C5	118.20 (15)	C14—C15—C10	118.93 (13)
C1—C6—C7	120.19 (15)	C14—C15—C16	119.71 (13)
C5—C6—C7	121.53 (15)	C10—C15—C16	121.36 (12)
C6—C7—S	105.99 (10)	N—C16—C15	121.71 (12)
C6—C7—H7A	110.5	N—C16—H16	119.1
S—C7—H7A	110.5	C15—C16—H16	119.1
C6—C7—H7B	110.5	C16—N—N^i	112.24 (14)
S—C7—H7B	110.5	C10—S—C7	105.25 (7)
H7A—C7—H7B	108.7
C6—C1—C2—C3	−0.3 (3)	C12—C13—C14—C15	−0.9 (2)
C1—C2—C3—C4	−0.8 (3)	C13—C14—C15—C10	−0.2 (2)
C2—C3—C4—C5	1.5 (3)	C13—C14—C15—C16	179.15 (14)
C3—C4—C5—C6	−1.0 (3)	C11—C10—C15—C14	1.3 (2)
C2—C1—C6—C5	0.7 (2)	S—C10—C15—C14	−175.67 (10)
C2—C1—C6—C7	−176.18 (16)	C11—C10—C15—C16	−178.00 (13)
C4—C5—C6—C1	0.0 (2)	S—C10—C15—C16	5.00 (18)
C4—C5—C6—C7	176.78 (16)	C14—C15—C16—N	12.7 (2)
C1—C6—C7—S	89.07 (16)	C10—C15—C16—N	−167.96 (14)
C5—C6—C7—S	−87.67 (16)	C15—C16—N—N^i	−178.43 (15)
C15—C10—C11—C12	−1.4 (2)	C11—C10—S—C7	23.22 (15)
S—C10—C11—C12	175.47 (12)	C15—C10—S—C7	−159.90 (12)
C10—C11—C12—C13	0.3 (3)	C6—C7—S—C10	173.57 (11)
C11—C12—C13—C14	0.9 (3)

Symmetry code: (i) −x+1, −y+1, −z.