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The title compound, C16H20N2O4S2, crystallizes in a `partially extended' conformation, with crystallographically imposed centrosymmetry and intermolecular N—H...O hydrogen bonding.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536800020298/bt6001sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536800020298/bt6001Isup2.hkl
Contains datablock I

CCDC reference: 155893

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.036
  • wR factor = 0.110
  • Data-to-parameter ratio = 15.3

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

General Notes

ABSTM_02 When printed, the submitted absorption T values will be replaced by the scaled T values. Since the ratio of scaled T's is identical to the ratio of reported T values, the scaling does not imply a change to the absorption corrections used in the study. Ratio of Tmax expected/reported 1.118 Tmax scaled 0.927 Tmin scaled 0.913

Comment top

1,2-Bis(p-toluenesulfonylamino)ethane, (I), was prepared for use as a starting material in the synthesis of N-substituted alkylaminopolycarboxylate compounds, which were sought for development as potential biomedical diagnostics. The molecule crystallizes in a `partially extended' conformation in which the tosyl group folds back towards the diaminoethane unit. The molecule possesses crystallographically imposed centrosymmetry and is associated in the crystal via intermolecular N—H···O hydrogen bonds.

Experimental top

The title compound was prepared according to the procedure of Vogel (1989) and recrystallized from methanol. Analysis calculated for C16H20N2O4S2: C 51.9, H 5.4, N, 7.6%; found: C 51.9, H 5.8; N, 7.5%.

Refinement top

H atoms were refined with fixed individual displacement parameters [U(H) = 1.2 Ueq(C), U(H) = 1.3 Ueq(Cmethyl) or U(H) = 1.2 Ueq(N)] using a riding model with N—H = 0.86, C—H(aromatic) = 0.93, CH(methylene) = 0.97 or CH(methyl) = 0.96 Å. The methyl group was allowed to rotate about its local threefold axis.

Computing details top

Data collection: CAD-4 Software (Enraf-Nonius, 1989); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1987); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.

Figures top
[Figure 1] Fig. 1. Perspective view of the title molecule. The pairs of atoms C1/C1A, O1/O1A etc are related by the crystallographic inversion centre.
N,N-Ethylenebis(p-toluenesulfonamide) top
Crystal data top
C16H20N2O4S2F(000) = 388
Mr = 368.46Dx = 1.421 Mg m3
Dm = 1.4 Mg m3
Dm measured by flotation
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 5.8070 (12) ÅCell parameters from 25 reflections
b = 8.0970 (16) Åθ = 14.2–18.7°
c = 18.513 (4) ŵ = 0.33 mm1
β = 98.35 (3)°T = 293 K
V = 861.2 (3) Å3Column, colourless
Z = 20.40 × 0.36 × 0.23 mm
Data collection top
Enraf-Nonius CAD-4
diffractometer
1283 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.025
Graphite monochromatorθmax = 26.0°, θmin = 2.2°
θ/2θ scansh = 77
Absorption correction: empirical (using intensity measurements)
via ψ scans (North et al., 1968)
k = 09
Tmin = 0.817, Tmax = 0.829l = 2222
3356 measured reflections2 standard reflections every 120 min
1682 independent reflections intensity decay: 4.3%
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)] = 0.036Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.110H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0683P)2 + 0.1576P]
where P = (Fo2 + 2Fc2)/3
1682 reflections(Δ/σ)max = 0.008
110 parametersΔρmax = 0.35 e Å3
0 restraintsΔρmin = 0.43 e Å3
Crystal data top
C16H20N2O4S2V = 861.2 (3) Å3
Mr = 368.46Z = 2
Monoclinic, P21/cMo Kα radiation
a = 5.8070 (12) ŵ = 0.33 mm1
b = 8.0970 (16) ÅT = 293 K
c = 18.513 (4) Å0.40 × 0.36 × 0.23 mm
β = 98.35 (3)°
Data collection top
Enraf-Nonius CAD-4
diffractometer
1283 reflections with I > 2σ(I)
Absorption correction: empirical (using intensity measurements)
via ψ scans (North et al., 1968)
Rint = 0.025
Tmin = 0.817, Tmax = 0.8292 standard reflections every 120 min
3356 measured reflections intensity decay: 4.3%
1682 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0360 restraints
wR(F2) = 0.110H-atom parameters constrained
S = 1.03Δρmax = 0.35 e Å3
1682 reflectionsΔρmin = 0.43 e Å3
110 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. All H-atoms were evident in difference maps but, particularly with those belonging to the methyl group (H8a—H8C) and that attached to N (H1N), attempts at refinement led to unreasonable geometries. Hence they were included as riding contributions using the appropriate SHELX HFIX instructions.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S0.33227 (9)0.80920 (6)0.06633 (3)0.04226 (19)
O10.2802 (3)0.97684 (18)0.04401 (9)0.0550 (4)
O20.1456 (3)0.69995 (18)0.07434 (9)0.0561 (4)
N0.4804 (3)0.7309 (2)0.00746 (9)0.0449 (4)
H1N0.50240.78530.03090.054*
C10.5770 (4)0.5640 (2)0.02103 (12)0.0456 (5)
H1A0.59220.53980.07280.055*
H1B0.73100.55940.00660.055*
C20.5207 (3)0.8128 (2)0.15055 (11)0.0399 (4)
C30.4609 (4)0.7327 (3)0.21059 (12)0.0505 (5)
H30.32050.67610.20730.061*
C40.6108 (4)0.7367 (3)0.27609 (13)0.0559 (6)
H40.56920.68320.31680.067*
C50.8209 (4)0.8189 (3)0.28171 (12)0.0505 (5)
C60.8781 (4)0.8988 (3)0.22000 (13)0.0547 (6)
H61.01850.95550.22310.066*
C70.7313 (4)0.8958 (3)0.15454 (12)0.0483 (5)
H70.77260.94840.11370.058*
C80.9848 (5)0.8232 (4)0.35324 (16)0.0740 (8)
H8A0.96230.92410.37850.096*
H8B1.14270.81730.34370.096*
H8C0.95310.73090.38290.096*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S0.0402 (3)0.0297 (3)0.0558 (3)0.00112 (19)0.0031 (2)0.0008 (2)
O10.0561 (9)0.0335 (8)0.0741 (10)0.0082 (6)0.0050 (7)0.0062 (7)
O20.0420 (8)0.0489 (9)0.0758 (11)0.0110 (7)0.0033 (7)0.0007 (7)
N0.0554 (10)0.0306 (8)0.0478 (9)0.0005 (7)0.0048 (8)0.0018 (7)
C10.0472 (11)0.0342 (10)0.0530 (11)0.0020 (9)0.0006 (9)0.0043 (8)
C20.0390 (9)0.0291 (9)0.0518 (10)0.0003 (7)0.0067 (8)0.0037 (8)
C30.0481 (12)0.0424 (11)0.0612 (13)0.0070 (9)0.0093 (10)0.0036 (9)
C40.0645 (14)0.0487 (12)0.0544 (12)0.0003 (11)0.0086 (11)0.0048 (10)
C50.0553 (13)0.0389 (11)0.0555 (12)0.0099 (9)0.0024 (10)0.0120 (9)
C60.0419 (11)0.0478 (13)0.0735 (14)0.0060 (9)0.0047 (10)0.0149 (11)
C70.0469 (11)0.0409 (11)0.0580 (12)0.0083 (9)0.0105 (9)0.0015 (9)
C80.0754 (17)0.0687 (17)0.0707 (16)0.0133 (13)0.0138 (13)0.0199 (13)
Geometric parameters (Å, º) top
S—O21.4236 (16)C2—C71.388 (3)
S—O11.4382 (15)C3—C41.386 (3)
S—N1.6134 (19)C4—C51.381 (3)
S—C21.770 (2)C5—C61.395 (3)
N—C11.470 (2)C5—C81.515 (3)
C1—C1i1.510 (4)C6—C71.377 (3)
C2—C31.374 (3)
O2—S—O1119.01 (10)C3—C2—S120.55 (16)
O2—S—N108.36 (10)C7—C2—S118.82 (16)
O1—S—N106.70 (9)C2—C3—C4119.8 (2)
O2—S—C2107.52 (10)C5—C4—C3120.8 (2)
O1—S—C2108.34 (9)C4—C5—C6118.4 (2)
N—S—C2106.23 (9)C4—C5—C8120.9 (2)
C1—N—S118.27 (14)C6—C5—C8120.8 (2)
N—C1—C1i111.1 (2)C7—C6—C5121.5 (2)
C3—C2—C7120.6 (2)C6—C7—C2118.9 (2)
C1—N—S—O1174.14 (14)N—S—O1—C2114.01 (11)
Symmetry code: (i) x+1, y+1, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N—H1N···O1ii0.862.342.971 (2)131
Symmetry code: (ii) x+1, y+2, z.

Experimental details

Crystal data
Chemical formulaC16H20N2O4S2
Mr368.46
Crystal system, space groupMonoclinic, P21/c
Temperature (K)293
a, b, c (Å)5.8070 (12), 8.0970 (16), 18.513 (4)
β (°) 98.35 (3)
V3)861.2 (3)
Z2
Radiation typeMo Kα
µ (mm1)0.33
Crystal size (mm)0.40 × 0.36 × 0.23
Data collection
DiffractometerEnraf-Nonius CAD-4
diffractometer
Absorption correctionEmpirical (using intensity measurements)
via ψ scans (North et al., 1968)
Tmin, Tmax0.817, 0.829
No. of measured, independent and
observed [I > 2σ(I)] reflections
3356, 1682, 1283
Rint0.025
(sin θ/λ)max1)0.616
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.036, 0.110, 1.03
No. of reflections1682
No. of parameters110
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.35, 0.43

Computer programs: CAD-4 Software (Enraf-Nonius, 1989), CAD-4 Software, XCAD4 (Harms & Wocadlo, 1987), SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1997), SHELXTL.

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N—H1N···O1i0.862.342.971 (2)131.0
Symmetry code: (i) x+1, y+2, z.
 

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