Literature DB >> 23795072

1,2-Bis{2-[(4-meth-oxy-benzyl-idene)amino]-phen-yl}disulfane.

Abstract

The asymmetric unit of the title compound, C28H24N2O2S2, contains one-half mol-ecule, 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 di-sulfide chain form a dihedral angle of 76.1 (1)°, while the planes of the two benzene rings in the benzyl-ideneaniline fragment form a dihedral angle of 48.9 (1)°. The crystal packing exhibits no significantly short inter-molecular contacts.

Entities: CellLine Chemical Disease Gene

Year: 2013 PMID： 23795072 PMCID： PMC3685053 DOI： 10.1107/S1600536813011598

Source DB: PubMed Journal: Acta Crystallogr Sect E Struct Rep Online ISSN： 1600-5368

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 = 484.61 Orthorhombic, 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[F 2 > 2σ(F 2)] = 0.051 wR(F 2) = 0.139 S = 0.95 2163 reflections 155 parameters H-atom parameters constrained Δρmax = 0.37 e Å−3 Δρmin = −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. Click here for additional data file. Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813011598/cv5405sup1.cif Click here for additional data file. Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813011598/cv5405Isup2.hkl Click here for additional data file. Supplementary material file. DOI: 10.1107/S1600536813011598/cv5405Isup3.cml Additional supplementary materials: crystallographic information; 3D view; checkCIF report

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

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 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

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.

	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*

	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)

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

3 in total

1,2-Bis{2-[(4-meth-oxy-benzyl-idene)amino]-phen-yl}disulfane.

Related literature

Experimental

Crystal data

Data collection

Refinement

1. A short history of SHELX.

2. Bis[2-(benzyl-idene-amino)-phen-yl] disulfide.

3. 2-{[4-(Dimethyl-amino)-benzyl-idene]amino}-phenyl disulfide.