1,2-Bis{2-[(4-meth­oxy­benzyl­idene)amino]­phen­yl}disulfane

Xin, W.

doi:10.1107/S1600536813011598

organic compounds

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Volume 69| Part 6| June 2013| Page o896

doi:10.1107/S1600536813011598

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1,2-Bis{2-[(4-methoxybenzylidene)amino]phenyl}disulfane

Wei Xin ^a ^*

^aKingfa Scientific & Technological Coporation Limited, Guang Zhou, China 510663, People's Republic of China
^*Correspondence e-mail: xinw0408@163.com

(Received 15 April 2013; accepted 28 April 2013; online 15 May 2013)

The asymmetric unit of the title compound, C₂₈H₂₄N₂O₂S₂, contains one-half molecule, which is completed by twofold rotation symmetry with the twofold axis passing through the mid-point of the central S—S bond. The planes of the two benzene rings linked by the disulfide chain form a dihedral angle of 76.1 (1)°, while the planes of the two benzene rings in the benzylideneaniline fragment form a dihedral angle of 48.9 (1)°. The crystal packing exhibits no significantly short intermolecular contacts.

Related literature

For the crystal structures of related compounds, see: İde et al. (1997 ); Ozbey et al. (1998 ); He et al. (2011 ); Wang et al. (2011 ).

Experimental

Crystal data

C₂₈H₂₄N₂O₂S₂
M_r = 484.61
Orthorhombic, P b c n
a = 10.2657 (11) Å
b = 13.0675 (13) Å
c = 18.3415 (15) Å
V = 2460.5 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.25 mm⁻¹
T = 298 K
0.26 × 0.22 × 0.17 mm

Data collection

Bruker SMART APEX CCD area-etector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.939, T_max = 0.960
9487 measured reflections
2163 independent reflections
1363 reflections with I > 2σ(I)
R_int = 0.094

Refinement

R[F² > 2σ(F²)] = 0.051
wR(F²) = 0.139
S = 0.95
2163 reflections
155 parameters
H-atom parameters constrained
Δρ_max = 0.37 e Å⁻³
Δρ_min = −0.28 e Å⁻³

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

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536813011598/cv5405sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813011598/cv5405Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813011598/cv5405Isup3.cml

checkCIF report

Comment top

As a contribution to structural study of diaminodiphenyl disulfides (İde et al., 1997; Wang et al., 2011; He et al., 2011), we present here the crystal structure of the title compound, (I).

In (I) (Fig. 1), the bond lengths and angles are normal and correspond to those observed in related compounds (İde et al., 1997; Ozbey et al.,1998; He et al., 2011). The molecule has crystallographic twofold rotation symmetry with the twofold axis passing through the midpoint of the central S—S bond. Two benzene rings connected through disulfide chain form a dihedral angle of 76.1 (1)°. Two benzene rings in two benzylideneaniline fragments form the dihedral angles of 48.9 (1)°. The crystal packing exhibits no significantly short intermolecular contacts.

Related literature top

For the crystal structures of related compounds, see: İde et al. (1997); Ozbey et al. (1998); He et al. (2011); Wang et al. (2011).

Experimental top

4-Methoxybenzaldehyde (2 mmol) in ethanol (10 ml) was added to a solution of 2,2'-diaminodiphenyl disulfide (1 mmol) in ethanol (20 ml). The solution was heated to 323 K for 4 h. The reaction mixture was cooled to room tempertature and the yellow crystalline product was obtained.

Computing details top

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

Figures top

Fig. 1. The molecular structure of (I) showing the atomic numbering and 50% probabilty displacement ellipsoids. Unlabelled atoms are related with the labelled ones by symmetry operation (-x, y, 1/2 - z).

1,2-Bis{2-[(4-methoxybenzylidene)amino]phenyl}disulfane top

Crystal data top

C₂₈H₂₄N₂O₂S₂	D_x = 1.308 Mg m⁻³
M_r = 484.61	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pbcn	Cell parameters from 1719 reflections
a = 10.2657 (11) Å	θ = 2.5–22.9°
b = 13.0675 (13) Å	µ = 0.25 mm⁻¹
c = 18.3415 (15) Å	T = 298 K
V = 2460.5 (4) Å³	Block, yellow
Z = 4	0.26 × 0.22 × 0.17 mm
F(000) = 1016

Data collection top

Bruker SMART APEX CCD area-etector diffractometer	2163 independent reflections
Radiation source: fine-focus sealed tube	1363 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.094
phi and ω scans	θ_max = 25.0°, θ_min = 2.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −8→12
T_min = 0.939, T_max = 0.960	k = −12→15
9487 measured reflections	l = −17→21

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.139	H-atom parameters constrained
S = 0.95	w = 1/[σ²(F_o²) + (0.075P)²] where P = (F_o² + 2F_c²)/3
2163 reflections	(Δ/σ)_max < 0.001
155 parameters	Δρ_max = 0.37 e Å⁻³
0 restraints	Δρ_min = −0.28 e Å⁻³

Crystal data top

C₂₈H₂₄N₂O₂S₂	V = 2460.5 (4) Å³
M_r = 484.61	Z = 4
Orthorhombic, Pbcn	Mo Kα radiation
a = 10.2657 (11) Å	µ = 0.25 mm⁻¹
b = 13.0675 (13) Å	T = 298 K
c = 18.3415 (15) Å	0.26 × 0.22 × 0.17 mm

Data collection top

Bruker SMART APEX CCD area-etector diffractometer	2163 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1363 reflections with I > 2σ(I)
T_min = 0.939, T_max = 0.960	R_int = 0.094
9487 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.051	0 restraints
wR(F²) = 0.139	H-atom parameters constrained
S = 0.95	Δρ_max = 0.37 e Å⁻³
2163 reflections	Δρ_min = −0.28 e Å⁻³
155 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.

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

	x	y	z	U_iso*/U_eq
S1	0.01987 (8)	0.02789 (6)	0.19518 (4)	0.0510 (3)
N1	0.1694 (2)	0.02278 (17)	0.06606 (11)	0.0433 (6)
O1	0.0529 (2)	0.39678 (18)	−0.14776 (12)	0.0757 (7)
C1	0.1483 (3)	−0.0635 (2)	0.18144 (14)	0.0408 (7)
C2	0.1829 (3)	−0.1399 (2)	0.23057 (15)	0.0494 (8)
H2	0.1390	−0.1459	0.2747	0.059*
C3	0.2830 (3)	−0.2067 (2)	0.21360 (16)	0.0574 (8)
H3	0.3062	−0.2575	0.2467	0.069*
C4	0.3491 (3)	−0.1991 (2)	0.14808 (16)	0.0596 (9)
H4	0.4153	−0.2450	0.1369	0.072*
C5	0.3159 (3)	−0.1225 (2)	0.09907 (15)	0.0510 (8)
H5	0.3605	−0.1171	0.0551	0.061*
C6	0.2160 (3)	−0.0532 (2)	0.11509 (14)	0.0417 (7)
C7	0.2471 (3)	0.0735 (2)	0.02534 (14)	0.0468 (7)
H7	0.3359	0.0594	0.0276	0.056*
C8	0.2011 (3)	0.1530 (2)	−0.02483 (13)	0.0451 (7)
C9	0.0684 (3)	0.1658 (2)	−0.03945 (14)	0.0483 (7)
H9	0.0089	0.1192	−0.0205	0.058*
C10	0.0241 (3)	0.2456 (2)	−0.08118 (15)	0.0518 (8)
H10	−0.0646	0.2524	−0.0902	0.062*
C11	0.1108 (3)	0.3167 (2)	−0.11021 (14)	0.0518 (8)
C12	0.2432 (3)	0.3044 (2)	−0.09884 (14)	0.0541 (8)
H12	0.3024	0.3505	−0.1187	0.065*
C13	0.2868 (3)	0.2216 (2)	−0.05696 (14)	0.0539 (8)
H13	0.3758	0.2123	−0.0505	0.065*
C14	0.1355 (4)	0.4714 (3)	−0.1798 (2)	0.0852 (12)
H14A	0.1930	0.4987	−0.1434	0.128*
H14B	0.0836	0.5257	−0.1998	0.128*
H14C	0.1859	0.4404	−0.2180	0.128*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0584 (6)	0.0438 (5)	0.0509 (5)	0.0064 (4)	0.0120 (4)	0.0093 (3)
N1	0.0474 (15)	0.0441 (13)	0.0383 (12)	−0.0016 (11)	0.0033 (11)	0.0047 (11)
O1	0.0769 (17)	0.0664 (16)	0.0839 (16)	−0.0040 (13)	−0.0048 (13)	0.0296 (13)
C1	0.0446 (18)	0.0362 (15)	0.0415 (15)	−0.0036 (13)	0.0016 (13)	−0.0014 (12)
C2	0.064 (2)	0.0450 (18)	0.0395 (15)	−0.0004 (15)	0.0080 (14)	0.0022 (13)
C3	0.069 (2)	0.0495 (19)	0.0536 (18)	0.0127 (17)	0.0051 (16)	0.0100 (15)
C4	0.064 (2)	0.054 (2)	0.061 (2)	0.0174 (16)	0.0045 (16)	0.0008 (16)
C5	0.054 (2)	0.0534 (19)	0.0451 (16)	0.0032 (16)	0.0130 (14)	−0.0001 (14)
C6	0.0428 (17)	0.0428 (16)	0.0395 (15)	−0.0035 (13)	−0.0009 (13)	−0.0001 (12)
C7	0.0447 (18)	0.0508 (17)	0.0449 (15)	−0.0015 (15)	0.0022 (14)	0.0015 (13)
C8	0.053 (2)	0.0492 (17)	0.0330 (14)	−0.0047 (14)	0.0048 (13)	−0.0003 (12)
C9	0.0509 (19)	0.0487 (18)	0.0452 (16)	−0.0089 (15)	0.0002 (14)	0.0031 (13)
C10	0.0499 (19)	0.0558 (19)	0.0496 (17)	−0.0019 (16)	−0.0017 (14)	0.0028 (15)
C11	0.063 (2)	0.0533 (19)	0.0389 (15)	−0.0033 (17)	−0.0038 (15)	0.0040 (14)
C12	0.065 (2)	0.0540 (19)	0.0436 (16)	−0.0157 (17)	0.0081 (15)	0.0101 (14)
C13	0.0511 (19)	0.066 (2)	0.0444 (16)	−0.0081 (16)	0.0066 (14)	0.0069 (15)
C14	0.101 (3)	0.065 (3)	0.090 (3)	−0.011 (2)	0.005 (2)	0.030 (2)

Geometric parameters (Å, º) top

S1—C1	1.797 (3)	C7—C8	1.466 (4)
S1—S1ⁱ	2.0518 (14)	C7—H7	0.9300
N1—C7	1.278 (3)	C8—C13	1.388 (4)
N1—C6	1.423 (3)	C8—C9	1.398 (4)
O1—C11	1.387 (4)	C9—C10	1.372 (4)
O1—C14	1.420 (4)	C9—H9	0.9300
C1—C2	1.390 (4)	C10—C11	1.392 (4)
C1—C6	1.408 (3)	C10—H10	0.9300
C2—C3	1.385 (4)	C11—C12	1.385 (4)
C2—H2	0.9300	C12—C13	1.400 (4)
C3—C4	1.383 (4)	C12—H12	0.9300
C3—H3	0.9300	C13—H13	0.9300
C4—C5	1.388 (4)	C14—H14A	0.9600
C4—H4	0.9300	C14—H14B	0.9600
C5—C6	1.398 (4)	C14—H14C	0.9600
C5—H5	0.9300

C1—S1—S1ⁱ	106.46 (9)	C13—C8—C9	117.3 (3)
C7—N1—C6	121.4 (2)	C13—C8—C7	121.3 (3)
C11—O1—C14	117.9 (3)	C9—C8—C7	121.3 (3)
C2—C1—C6	120.1 (3)	C10—C9—C8	121.4 (3)
C2—C1—S1	125.0 (2)	C10—C9—H9	119.3
C6—C1—S1	114.8 (2)	C8—C9—H9	119.3
C3—C2—C1	119.8 (3)	C9—C10—C11	120.6 (3)
C3—C2—H2	120.1	C9—C10—H10	119.7
C1—C2—H2	120.1	C11—C10—H10	119.7
C4—C3—C2	120.9 (3)	C12—C11—O1	125.7 (3)
C4—C3—H3	119.6	C12—C11—C10	119.5 (3)
C2—C3—H3	119.6	O1—C11—C10	114.8 (3)
C3—C4—C5	119.7 (3)	C11—C12—C13	119.1 (3)
C3—C4—H4	120.2	C11—C12—H12	120.5
C5—C4—H4	120.2	C13—C12—H12	120.5
C4—C5—C6	120.7 (3)	C8—C13—C12	122.0 (3)
C4—C5—H5	119.7	C8—C13—H13	119.0
C6—C5—H5	119.7	C12—C13—H13	119.0
C5—C6—C1	118.8 (2)	O1—C14—H14A	109.5
C5—C6—N1	124.4 (2)	O1—C14—H14B	109.5
C1—C6—N1	116.5 (2)	H14A—C14—H14B	109.5
N1—C7—C8	122.2 (3)	O1—C14—H14C	109.5
N1—C7—H7	118.9	H14A—C14—H14C	109.5
C8—C7—H7	118.9	H14B—C14—H14C	109.5

Symmetry code: (i) −x, y, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₂₈H₂₄N₂O₂S₂
M_r	484.61
Crystal system, space group	Orthorhombic, Pbcn
Temperature (K)	298
a, b, c (Å)	10.2657 (11), 13.0675 (13), 18.3415 (15)
V (Å³)	2460.5 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.25
Crystal size (mm)	0.26 × 0.22 × 0.17

Data collection
Diffractometer	Bruker SMART APEX CCD area-etector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.939, 0.960
No. of measured, independent and observed [I > 2σ(I)] reflections	9487, 2163, 1363
R_int	0.094
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.051, 0.139, 0.95
No. of reflections	2163
No. of parameters	155
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.37, −0.28

Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Acknowledgements

The author acknowledges the financial support of the Kingfa Scientific & Technological corporation Ltd.

References

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