Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536800020298/bt6001sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536800020298/bt6001Isup2.hkl |
CCDC reference: 155893
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (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
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%.
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, C—H(methylene) = 0.97 or C—H(methyl) = 0.96 Å. The methyl group was allowed to rotate about its local threefold axis.
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.
Fig. 1. Perspective view of the title molecule. The pairs of atoms C1/C1A, O1/O1A etc are related by the crystallographic inversion centre. |
C16H20N2O4S2 | F(000) = 388 |
Mr = 368.46 | Dx = 1.421 Mg m−3 Dm = 1.4 Mg m−3 Dm measured by flotation |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 5.8070 (12) Å | Cell parameters from 25 reflections |
b = 8.0970 (16) Å | θ = 14.2–18.7° |
c = 18.513 (4) Å | µ = 0.33 mm−1 |
β = 98.35 (3)° | T = 293 K |
V = 861.2 (3) Å3 | Column, colourless |
Z = 2 | 0.40 × 0.36 × 0.23 mm |
Enraf-Nonius CAD-4 diffractometer | 1283 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.025 |
Graphite monochromator | θmax = 26.0°, θmin = 2.2° |
θ/2θ scans | h = −7→7 |
Absorption correction: empirical (using intensity measurements) via ψ scans (North et al., 1968) | k = 0→9 |
Tmin = 0.817, Tmax = 0.829 | l = −22→22 |
3356 measured reflections | 2 standard reflections every 120 min |
1682 independent reflections | intensity decay: 4.3% |
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)] = 0.036 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.110 | H-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 parameters | Δρmax = 0.35 e Å−3 |
0 restraints | Δρmin = −0.43 e Å−3 |
C16H20N2O4S2 | V = 861.2 (3) Å3 |
Mr = 368.46 | Z = 2 |
Monoclinic, P21/c | Mo Kα radiation |
a = 5.8070 (12) Å | µ = 0.33 mm−1 |
b = 8.0970 (16) Å | T = 293 K |
c = 18.513 (4) Å | 0.40 × 0.36 × 0.23 mm |
β = 98.35 (3)° |
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 = 0.829 | 2 standard reflections every 120 min |
3356 measured reflections | intensity decay: 4.3% |
1682 independent reflections |
R[F2 > 2σ(F2)] = 0.036 | 0 restraints |
wR(F2) = 0.110 | H-atom parameters constrained |
S = 1.03 | Δρmax = 0.35 e Å−3 |
1682 reflections | Δρmin = −0.43 e Å−3 |
110 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
S | 0.33227 (9) | 0.80920 (6) | 0.06633 (3) | 0.04226 (19) | |
O1 | 0.2802 (3) | 0.97684 (18) | 0.04401 (9) | 0.0550 (4) | |
O2 | 0.1456 (3) | 0.69995 (18) | 0.07434 (9) | 0.0561 (4) | |
N | 0.4804 (3) | 0.7309 (2) | 0.00746 (9) | 0.0449 (4) | |
H1N | 0.5024 | 0.7853 | −0.0309 | 0.054* | |
C1 | 0.5770 (4) | 0.5640 (2) | 0.02103 (12) | 0.0456 (5) | |
H1A | 0.5922 | 0.5398 | 0.0728 | 0.055* | |
H1B | 0.7310 | 0.5594 | 0.0066 | 0.055* | |
C2 | 0.5207 (3) | 0.8128 (2) | 0.15055 (11) | 0.0399 (4) | |
C3 | 0.4609 (4) | 0.7327 (3) | 0.21059 (12) | 0.0505 (5) | |
H3 | 0.3205 | 0.6761 | 0.2073 | 0.061* | |
C4 | 0.6108 (4) | 0.7367 (3) | 0.27609 (13) | 0.0559 (6) | |
H4 | 0.5692 | 0.6832 | 0.3168 | 0.067* | |
C5 | 0.8209 (4) | 0.8189 (3) | 0.28171 (12) | 0.0505 (5) | |
C6 | 0.8781 (4) | 0.8988 (3) | 0.22000 (13) | 0.0547 (6) | |
H6 | 1.0185 | 0.9555 | 0.2231 | 0.066* | |
C7 | 0.7313 (4) | 0.8958 (3) | 0.15454 (12) | 0.0483 (5) | |
H7 | 0.7726 | 0.9484 | 0.1137 | 0.058* | |
C8 | 0.9848 (5) | 0.8232 (4) | 0.35324 (16) | 0.0740 (8) | |
H8A | 0.9623 | 0.9241 | 0.3785 | 0.096* | |
H8B | 1.1427 | 0.8173 | 0.3437 | 0.096* | |
H8C | 0.9531 | 0.7309 | 0.3829 | 0.096* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S | 0.0402 (3) | 0.0297 (3) | 0.0558 (3) | −0.00112 (19) | 0.0031 (2) | 0.0008 (2) |
O1 | 0.0561 (9) | 0.0335 (8) | 0.0741 (10) | 0.0082 (6) | 0.0050 (7) | 0.0062 (7) |
O2 | 0.0420 (8) | 0.0489 (9) | 0.0758 (11) | −0.0110 (7) | 0.0033 (7) | 0.0007 (7) |
N | 0.0554 (10) | 0.0306 (8) | 0.0478 (9) | 0.0005 (7) | 0.0048 (8) | 0.0018 (7) |
C1 | 0.0472 (11) | 0.0342 (10) | 0.0530 (11) | 0.0020 (9) | −0.0006 (9) | −0.0043 (8) |
C2 | 0.0390 (9) | 0.0291 (9) | 0.0518 (10) | −0.0003 (7) | 0.0067 (8) | −0.0037 (8) |
C3 | 0.0481 (12) | 0.0424 (11) | 0.0612 (13) | −0.0070 (9) | 0.0093 (10) | 0.0036 (9) |
C4 | 0.0645 (14) | 0.0487 (12) | 0.0544 (12) | 0.0003 (11) | 0.0086 (11) | 0.0048 (10) |
C5 | 0.0553 (13) | 0.0389 (11) | 0.0555 (12) | 0.0099 (9) | 0.0024 (10) | −0.0120 (9) |
C6 | 0.0419 (11) | 0.0478 (13) | 0.0735 (14) | −0.0060 (9) | 0.0047 (10) | −0.0149 (11) |
C7 | 0.0469 (11) | 0.0409 (11) | 0.0580 (12) | −0.0083 (9) | 0.0105 (9) | −0.0015 (9) |
C8 | 0.0754 (17) | 0.0687 (17) | 0.0707 (16) | 0.0133 (13) | −0.0138 (13) | −0.0199 (13) |
S—O2 | 1.4236 (16) | C2—C7 | 1.388 (3) |
S—O1 | 1.4382 (15) | C3—C4 | 1.386 (3) |
S—N | 1.6134 (19) | C4—C5 | 1.381 (3) |
S—C2 | 1.770 (2) | C5—C6 | 1.395 (3) |
N—C1 | 1.470 (2) | C5—C8 | 1.515 (3) |
C1—C1i | 1.510 (4) | C6—C7 | 1.377 (3) |
C2—C3 | 1.374 (3) | ||
O2—S—O1 | 119.01 (10) | C3—C2—S | 120.55 (16) |
O2—S—N | 108.36 (10) | C7—C2—S | 118.82 (16) |
O1—S—N | 106.70 (9) | C2—C3—C4 | 119.8 (2) |
O2—S—C2 | 107.52 (10) | C5—C4—C3 | 120.8 (2) |
O1—S—C2 | 108.34 (9) | C4—C5—C6 | 118.4 (2) |
N—S—C2 | 106.23 (9) | C4—C5—C8 | 120.9 (2) |
C1—N—S | 118.27 (14) | C6—C5—C8 | 120.8 (2) |
N—C1—C1i | 111.1 (2) | C7—C6—C5 | 121.5 (2) |
C3—C2—C7 | 120.6 (2) | C6—C7—C2 | 118.9 (2) |
C1—N—S—O1 | 174.14 (14) | N—S—O1—C2 | −114.01 (11) |
Symmetry code: (i) −x+1, −y+1, −z. |
D—H···A | D—H | H···A | D···A | D—H···A |
N—H1N···O1ii | 0.86 | 2.34 | 2.971 (2) | 131 |
Symmetry code: (ii) −x+1, −y+2, −z. |
Experimental details
Crystal data | |
Chemical formula | C16H20N2O4S2 |
Mr | 368.46 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 293 |
a, b, c (Å) | 5.8070 (12), 8.0970 (16), 18.513 (4) |
β (°) | 98.35 (3) |
V (Å3) | 861.2 (3) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.33 |
Crystal size (mm) | 0.40 × 0.36 × 0.23 |
Data collection | |
Diffractometer | Enraf-Nonius CAD-4 diffractometer |
Absorption correction | Empirical (using intensity measurements) via ψ scans (North et al., 1968) |
Tmin, Tmax | 0.817, 0.829 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 3356, 1682, 1283 |
Rint | 0.025 |
(sin θ/λ)max (Å−1) | 0.616 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.036, 0.110, 1.03 |
No. of reflections | 1682 |
No. of parameters | 110 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 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.
D—H···A | D—H | H···A | D···A | D—H···A |
N—H1N···O1i | 0.86 | 2.34 | 2.971 (2) | 131.0 |
Symmetry code: (i) −x+1, −y+2, −z. |
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.