Download citation
Download citation
link to html
The crystal structure of 2,4,6-triisopropylbenzenesulfonamide, C15H25NO2S, has been solved from X-ray powder diffraction data collected at 120 (1) K using synchrotron radiation and refined by Rietveld methods. The structure was solved by the application of a Monte Carlo method in which trial structures were generated by random movement of the molecule in the unit cell and assessed using a full-profile-fitting technique. Intramolecular flexibility was introduced into the structure solution in the form of four independent asymmetric rotors, allowing the isopropyl and sulfonamide groups to rotate freely within the molecule. The structure is monoclinic P21/c, a = 16.9600 (6), b = 8.1382 (2), c = 11.7810 (2) Å, β = 104.777 (2)° with Z = 4. The molecules are linked by N—H...O hydrogen bonds, with N...O distances of 2.77 (1) and 2.92 (1) Å, into two-dimensional sheets built from R^2_2(8) and R^6_6(20) rings.

Supporting information

cif

Crystallographic Information File (CIF)
Contains datablocks global, TIBS

hkl

Structure factor file (CIF format)
Supplementary material

CCDC reference: 138582

Computing details top

Data collection: PINCER (CCLRC, 1994); program(s) used to solve structure: OCTOPUS (Tremayne et al. 1997); program(s) used to refine structure: GSAS (Larson et al. 1994).

2,4,6-Tri-isopropylbenzenesulfonamide top
Crystal data top
C15H25NO2SV = 1572.3 (1) Å3
Mr = 283.42Z = 4
Monoclinic, P21/cDx = 1.200 Mg m3
a = 16.9600 (6) ÅSynchrotron radiation
b = 8.1382 (2) ÅT = 120 K
c = 11.7810 (2) Åwhite
β = 104.777 (2)°cylinder, 30 × 0.5 mm
Data collection top
Bede EDR detector
diffractometer
Specimen mounting: quartz capillary
Radiation source: synchrotronData collection mode: transmission
Silicon 111 monochromator2θmin = 3.00°, 2θmax = 49.99°, 2θstep = 0.01°
Refinement top
Rp = 0.050143 parameters
Rwp = 0.071120 restraints
R(F2) = 0.0997Restr
Excluded region(s): 7 small regions excluded due to ice peaksPreferred orientation correction: none
Profile function: pseudovoigt
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S10.0849 (5)0.3869 (9)0.6677 (6)0.072 (4)*
C10.186 (1)0.481 (3)0.709 (2)0.039 (4)*
C20.199 (1)0.627 (3)0.647 (2)0.039 (4)*
C30.274 (1)0.705 (2)0.686 (2)0.039 (4)*
C40.337 (1)0.634 (2)0.773 (2)0.039 (4)*
C50.323 (1)0.497 (3)0.834 (1)0.039 (4)*
C60.247 (1)0.414 (3)0.798 (2)0.039 (4)*
C70.1306 (7)0.715 (1)0.551 (1)0.064 (6)*
C80.4210 (9)0.723 (1)0.811 (1)0.064 (6)*
C90.2456 (6)0.241 (2)0.857 (1)0.064 (6)*
O10.0724 (8)0.349 (2)0.550 (1)0.046 (5)*
O20.0771 (8)0.265 (2)0.741 (1)0.046 (5)*
N10.0199 (9)0.540 (2)0.681 (1)0.017 (7)*
C710.1659 (9)0.715 (2)0.447 (1)0.063 (4)*
C720.1057 (8)0.876 (2)0.593 (1)0.063 (4)*
C810.4853 (9)0.625 (2)0.775 (1)0.063 (4)*
C820.4501 (9)0.759 (2)0.940 (1)0.063 (4)*
C910.2575 (9)0.265 (2)0.985 (1)0.063 (4)*
C920.3061 (9)0.123 (2)0.830 (1)0.063 (4)*
H30.285 (4)0.824 (9)0.647 (9)0.05*
H50.364 (4)0.465 (9)0.920 (6)0.05*
H70.079 (1)0.630 (2)0.535 (2)0.05*
H80.412 (1)0.840 (2)0.762 (2)0.05*
H90.183 (1)0.195 (3)0.818 (2)0.05*
H7110.166 (7)0.589 (3)0.414 (7)0.07*
H7120.128 (5)0.794 (9)0.378 (5)0.07*
H7130.228 (3)0.763 (9)0.472 (4)0.07*
H7210.159 (3)0.960 (6)0.613 (9)0.07*
H7220.056 (6)0.930 (8)0.524 (5)0.07*
H7230.084 (7)0.856 (4)0.672 (6)0.07*
H8110.467 (4)0.495 (3)0.768 (9)0.07*
H8120.492 (6)0.670 (9)0.690 (6)0.07*
H8130.543 (2)0.638 (9)0.842 (6)0.07*
H8210.477 (6)0.648 (4)0.987 (2)0.07*
H8220.496 (4)0.858 (8)0.954 (2)0.07*
H8230.398 (2)0.799 (9)0.974 (3)0.07*
H9110.198 (1)0.277 (9)1.006 (2)0.07*
H9120.290 (6)0.159 (7)1.033 (2)0.07*
H9130.293 (6)0.377 (8)1.014 (3)0.07*
H9210.294 (6)0.001 (3)0.859 (9)0.07*
H9220.301 (6)0.123 (9)0.735 (2)0.07*
H9230.368 (1)0.160 (9)0.877 (9)0.07*
Geometric parameters (Å, º) top
S1—O11.38 (1)C3—H31.11 (1)
S1—O21.34 (1)C5—H51.10 (1)
S1—N11.70 (1)C7—H71.09 (1)
S1—C11.83 (1)C8—H81.10 (1)
C2—C71.57 (1)C9—H91.11 (3)
C4—C81.56 (1)C71—H7111.10 (1)
C6—C91.57 (1)C71—H7121.10 (1)
C7—C711.494 (7)C71—H7131.10 (1)
C7—C721.499 (7)C72—H7211.11 (1)
C8—C811.497 (7)C72—H7221.10 (1)
C8—C821.502 (7)C72—H7231.10 (1)
C9—C911.484 (7)C81—H8111.10 (1)
C9—C921.497 (7)C81—H8121.10 (1)
N1—H11.003 (13)C81—H8131.09 (1)
N1—H21.001 (13)C82—H8211.10 (1)
N1—O1i2.92 (1)C82—H8221.10 (1)
N1—O2ii2.77 (1)C82—H8231.11 (1)
C1—C21.44 (1)C91—H9111.10 (1)
C1—C61.38 (1)C91—H9121.10 (1)
C2—C31.39 (1)C91—H9131.10 (1)
C3—C41.40 (1)C92—H9211.10 (1)
C4—C51.38 (1)C92—H9221.10 (1)
C5—C61.42 (1)C92—H9231.10 (1)
O1—S1—O2117 (1)C6—C9—H9104 (1)
O1—S1—N1109 (1)C91—C9—H9109 (1)
C1—S1—O1105 (1)C92—C9—H9109 (1)
O2—S1—N1108 (1)C7—C71—H711109 (1)
C1—S1—O2112 (1)C7—C71—H712109 (1)
C1—S1—N1105 (1)C7—C71—H713110 (1)
S1—C1—C2118 (1)H711—C71—H712110 (1)
S1—C1—C6120 (1)H711—C71—H713110 (1)
C1—C2—C7124 (1)H712—C71—H713109 (1)
C3—C2—C7118 (1)C7—C72—H721109 (1)
C1—C6—C9126 (1)C7—C72—H722109 (1)
C5—C6—C9114 (1)C7—C72—H723109 (1)
C3—C4—C8119 (1)H721—C72—H722110 (1)
C5—C4—C8119 (1)H721—C72—H723110 (1)
C2—C7—C71102 (1)H722—C72—H723109 (1)
C2—C7—C72112 (1)C8—C81—H811109 (1)
C71—C7—C72118 (1)C8—C81—H812109 (1)
C4—C8—C81110 (1)C8—C81—H813109 (1)
C4—C8—C82115 (1)H811—C81—H812110 (1)
C81—C8—C82108 (1)H811—C81—H813109 (1)
C6—C9—C91109 (1)H812—C81—H813110 (1)
C6—C9—C92113 (1)C8—C82—H821110 (1)
C91—C9—C92112 (1)C8—C82—H822109 (1)
C2—C1—C6122 (1)C8—C82—H823110 (1)
C1—C2—C3117 (1)H821—C82—H822110 (1)
C2—C3—C4121 (1)H821—C82—H823109 (1)
C3—C4—C5121 (1)H822—C82—H823109 (1)
C4—C5—C6119 (1)C9—C91—H911110 (1)
C1—C6—C5119 (1)C9—C91—H912110 (1)
C2—C3—H3120 (1)C9—C91—H913110 (1)
C4—C3—H3119 (1)H911—C91—H912109 (1)
C4—C5—H5121 (1)H911—C91—H913109 (1)
C6—C5—H5118 (1)H912—C91—H913109 (1)
C2—C7—H7104 (1)C9—C92—H921109 (1)
C71—C7—H7109 (1)C9—C92—H922110 (1)
C72—C7—H7109 (1)C9—C92—H923110 (1)
C4—C8—H8105 (1)H921—C92—H922110 (1)
C81—C8—H8109 (1)H921—C92—H923110 (1)
C82—C8—H8109 (1)H922—C92—H923111 (1)
C1—C2—C7—C71123 (1)C1—C2—C7—C72109 (1)
C3—C4—C8—C81113 (1)C3—C4—C8—C82124 (1)
C1—C6—C9—C91122 (1)C1—C6—C9—C92113 (1)
C2—C1—S1—O159 (1)C2—C1—S1—O2172 (1)
C2—C1—S1—N155 (1)
Symmetry codes: (i) x, y+1, z+1; (ii) x, y+1/2, z+3/2.
 
Follow Acta Cryst. B
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds