1-(N-p-toluenesulfonyl)ethylaminoindene

Ortep of (1-N-p-toluenesulfonyl)ethylaminoindene
Figure 1: View of (1-N-p-toluenesulfonyl)ethylaminoindene showing the labelling of the non-H atoms. Thermal ellipsoids are shown at 40% probability levels.

The structure shows this molecule to be a 1,2-disubstituted ethane with a regular indenyl moiety substituted at the 1 carbon of the five membered ring and having the double bond in the expected 1 position (C(1)...C(2) 1.34 ) The sulfonamido moiety displays a planar nitrogen atom. There are no significant deviations from expected bond lengths and angles in the molecule. An active molecule (in .pdb format) is available here.

G.J. Gainsford, C. Lensink Acta Cryst. C, 1996, 52, 2.

Crystal data and structure refinement
Selected bond lengths and angles

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Table 1.  Crystal data and structure refinement for 4a. 
 
Identification code               [C455]shelxl 
Empirical formula                 C18 H19 N O2 S 
Formula weight                    313.40 
Temperature                       130(2) K 
Wavelength                        0.71073 A 
Crystal system                    Monoclinic 
Space group                       P 2~1~/n 
Unit cell dimensions              a = 12.681(7) A   alpha = 90 deg. 
                                  b = 7.261(4) A    beta = 93.65(2) deg. 
                                  c = 16.654(9) A   gamma = 90 deg. 
Volume                            1530.3(15) A^3 
Z                                 4 
Density (calculated)              1.360 Mg/m^3 
Absorption coefficient            0.218 mm^-1 
F(000)                            664 
Crystal size                      0.82 x 0.18 x 0.08 mm 
Theta range for data collection   2.08 to 24.98 deg. 
Index ranges                      -15<=h<=2, 0<=k<=8, -19<=l<=19 
Reflections collected             3216 
independent reflections           2693 [r(int) = 0.0272] 
absorption correction             \y scan 
max. and min. transmission        0.768 and 0.736 
refinement method                 full-matrix least-squares on f^2 
data / restraints / parameters    2693 / 0 / 204 
goodness-of-fit on f^2            1.044 
final r indices [i>2sigma(I)]     R1 = 0.0454, wR2 = 0.0925 
R indices (all data)              R1 = 0.0731, wR2 = 0.1053 
Extinction coefficient            0.0 
Largest diff. peak and hole       0.219 and -0.330 e.A^-3 

           Table 2.   Selected bond lengths [A] and angles [deg] for 4a. 
           _____________________________________________________________ 
  
            S(1)-O(1)                     1.431(2) 
            S(1)-O(2)                     1.435(2) 
            S(1)-N(1)                     1.600(3) 
            S(1)-C(14)                    1.768(3) 
            N(1)-C(10)                    1.467(4) 
            C(1)-C(2)                     1.340(4) 
            C(1)-C(9)                     1.475(3) 
            C(1)-C(18)                    1.500(4) 
            C(2)-C(3)                     1.493(4) 
            C(3)-C(8)                     1.501(3) 
            C(4)-C(8)                     1.380(4) 
            C(4)-C(5)                     1.398(4) 
            C(5)-C(6)                     1.381(4) 
            C(6)-C(7)                     1.388(4) 
            C(7)-C(9)                     1.389(4) 
            C(8)-C(9)                     1.398(4) 
            C(10)-C(18)                   1.530(4) 
            C(11)-C(16)                   1.390(4) 
            C(11)-C(12)                   1.394(4) 
            C(11)-C(17)                   1.506(3) 
            C(12)-C(13)                   1.388(3) 
            C(13)-C(14)                   1.389(3) 
            C(14)-C(15)                   1.389(3) 
            C(15)-C(16)                   1.377(4) 
  
            O(1)-S(1)-O(2)              119.49(12) 
            O(1)-S(1)-N(1)              107.40(13) 
            O(2)-S(1)-N(1)              106.52(12) 
            O(1)-S(1)-C(14)             107.11(11) 
            O(2)-S(1)-C(14)             106.77(11) 
            N(1)-S(1)-C(14)             109.30(13) 
            C(10)-N(1)-S(1)             123.5(2) 
            C(2)-C(1)-C(9)              108.0(2) 
            C(2)-C(1)-C(18)             128.2(2) 
            C(9)-C(1)-C(18)             123.8(2) 
            C(1)-C(2)-C(3)              111.9(2) 
            C(2)-C(3)-C(8)              102.7(2) 
            C(8)-C(4)-C(5)              118.6(3) 
            C(6)-C(5)-C(4)              120.5(2) 
            C(5)-C(6)-C(7)              121.1(3) 
            C(6)-C(7)-C(9)              118.6(3) 
            C(4)-C(8)-C(9)              120.9(2) 
            C(4)-C(8)-C(3)              130.6(2) 
            C(9)-C(8)-C(3)              108.5(2) 
            C(7)-C(9)-C(8)              120.3(2) 
            C(7)-C(9)-C(1)              131.0(2) 
            C(8)-C(9)-C(1)              108.7(2) 
            N(1)-C(10)-C(18)            111.0(2) 
            C(16)-C(11)-C(12)           118.3(2) 
            C(16)-C(11)-C(17)           120.5(2) 
            C(12)-C(11)-C(17)           121.2(2) 
            C(13)-C(12)-C(11)           121.2(2) 
            C(12)-C(13)-C(14)           119.2(2) 
            C(15)-C(14)-C(13)           120.4(2) 
            C(15)-C(14)-S(1)            119.9(2) 
            C(13)-C(14)-S(1)            119.7(2) 
            C(16)-C(15)-C(14)           119.6(2) 
            C(15)-C(16)-C(11)           121.4(2) 
            C(1)-C(18)-C(10)            113.3(2) 

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