research papers
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—HO hydrogen bonds, with NO distances of 2.77 (1) and 2.92 (1) Å, into two-dimensional sheets built from and rings.
Keywords: 2,4,6-Triisopropylbenzenesulfonamide; Monte Carlo structure solution; X-ray powder diffraction; Synchrotron radiation.
Supporting information
Crystallographic Information File (CIF) | |
Structure factor file (CIF format) |
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
C15H25NO2S | V = 1572.3 (1) Å3 |
Mr = 283.42 | Z = 4 |
Monoclinic, P21/c | Dx = 1.200 Mg m−3 |
a = 16.9600 (6) Å | Synchrotron radiation |
b = 8.1382 (2) Å | T = 120 K |
c = 11.7810 (2) Å | white |
β = 104.777 (2)° | cylinder, 30 × 0.5 mm |
Data collection top
Bede EDR detector diffractometer | Specimen mounting: quartz capillary |
Radiation source: synchrotron | Data collection mode: transmission |
Silicon 111 monochromator | 2θmin = 3.00°, 2θmax = 49.99°, 2θstep = 0.01° |
Refinement top
Rp = 0.050 | 143 parameters |
Rwp = 0.071 | 120 restraints |
R(F2) = 0.0997 | Restr |
Excluded region(s): 7 small regions excluded due to ice peaks | Preferred orientation correction: none |
Profile function: pseudovoigt |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
S1 | 0.0849 (5) | 0.3869 (9) | 0.6677 (6) | 0.072 (4)* | |
C1 | 0.186 (1) | 0.481 (3) | 0.709 (2) | 0.039 (4)* | |
C2 | 0.199 (1) | 0.627 (3) | 0.647 (2) | 0.039 (4)* | |
C3 | 0.274 (1) | 0.705 (2) | 0.686 (2) | 0.039 (4)* | |
C4 | 0.337 (1) | 0.634 (2) | 0.773 (2) | 0.039 (4)* | |
C5 | 0.323 (1) | 0.497 (3) | 0.834 (1) | 0.039 (4)* | |
C6 | 0.247 (1) | 0.414 (3) | 0.798 (2) | 0.039 (4)* | |
C7 | 0.1306 (7) | 0.715 (1) | 0.551 (1) | 0.064 (6)* | |
C8 | 0.4210 (9) | 0.723 (1) | 0.811 (1) | 0.064 (6)* | |
C9 | 0.2456 (6) | 0.241 (2) | 0.857 (1) | 0.064 (6)* | |
O1 | 0.0724 (8) | 0.349 (2) | 0.550 (1) | 0.046 (5)* | |
O2 | 0.0771 (8) | 0.265 (2) | 0.741 (1) | 0.046 (5)* | |
N1 | 0.0199 (9) | 0.540 (2) | 0.681 (1) | 0.017 (7)* | |
C71 | 0.1659 (9) | 0.715 (2) | 0.447 (1) | 0.063 (4)* | |
C72 | 0.1057 (8) | 0.876 (2) | 0.593 (1) | 0.063 (4)* | |
C81 | 0.4853 (9) | 0.625 (2) | 0.775 (1) | 0.063 (4)* | |
C82 | 0.4501 (9) | 0.759 (2) | 0.940 (1) | 0.063 (4)* | |
C91 | 0.2575 (9) | 0.265 (2) | 0.985 (1) | 0.063 (4)* | |
C92 | 0.3061 (9) | 0.123 (2) | 0.830 (1) | 0.063 (4)* | |
H3 | 0.285 (4) | 0.824 (9) | 0.647 (9) | 0.05* | |
H5 | 0.364 (4) | 0.465 (9) | 0.920 (6) | 0.05* | |
H7 | 0.079 (1) | 0.630 (2) | 0.535 (2) | 0.05* | |
H8 | 0.412 (1) | 0.840 (2) | 0.762 (2) | 0.05* | |
H9 | 0.183 (1) | 0.195 (3) | 0.818 (2) | 0.05* | |
H711 | 0.166 (7) | 0.589 (3) | 0.414 (7) | 0.07* | |
H712 | 0.128 (5) | 0.794 (9) | 0.378 (5) | 0.07* | |
H713 | 0.228 (3) | 0.763 (9) | 0.472 (4) | 0.07* | |
H721 | 0.159 (3) | 0.960 (6) | 0.613 (9) | 0.07* | |
H722 | 0.056 (6) | 0.930 (8) | 0.524 (5) | 0.07* | |
H723 | 0.084 (7) | 0.856 (4) | 0.672 (6) | 0.07* | |
H811 | 0.467 (4) | 0.495 (3) | 0.768 (9) | 0.07* | |
H812 | 0.492 (6) | 0.670 (9) | 0.690 (6) | 0.07* | |
H813 | 0.543 (2) | 0.638 (9) | 0.842 (6) | 0.07* | |
H821 | 0.477 (6) | 0.648 (4) | 0.987 (2) | 0.07* | |
H822 | 0.496 (4) | 0.858 (8) | 0.954 (2) | 0.07* | |
H823 | 0.398 (2) | 0.799 (9) | 0.974 (3) | 0.07* | |
H911 | 0.198 (1) | 0.277 (9) | 1.006 (2) | 0.07* | |
H912 | 0.290 (6) | 0.159 (7) | 1.033 (2) | 0.07* | |
H913 | 0.293 (6) | 0.377 (8) | 1.014 (3) | 0.07* | |
H921 | 0.294 (6) | −0.001 (3) | 0.859 (9) | 0.07* | |
H922 | 0.301 (6) | 0.123 (9) | 0.735 (2) | 0.07* | |
H923 | 0.368 (1) | 0.160 (9) | 0.877 (9) | 0.07* |
Geometric parameters (Å, º) top
S1—O1 | 1.38 (1) | C3—H3 | 1.11 (1) |
S1—O2 | 1.34 (1) | C5—H5 | 1.10 (1) |
S1—N1 | 1.70 (1) | C7—H7 | 1.09 (1) |
S1—C1 | 1.83 (1) | C8—H8 | 1.10 (1) |
C2—C7 | 1.57 (1) | C9—H9 | 1.11 (3) |
C4—C8 | 1.56 (1) | C71—H711 | 1.10 (1) |
C6—C9 | 1.57 (1) | C71—H712 | 1.10 (1) |
C7—C71 | 1.494 (7) | C71—H713 | 1.10 (1) |
C7—C72 | 1.499 (7) | C72—H721 | 1.11 (1) |
C8—C81 | 1.497 (7) | C72—H722 | 1.10 (1) |
C8—C82 | 1.502 (7) | C72—H723 | 1.10 (1) |
C9—C91 | 1.484 (7) | C81—H811 | 1.10 (1) |
C9—C92 | 1.497 (7) | C81—H812 | 1.10 (1) |
N1—H1 | 1.003 (13) | C81—H813 | 1.09 (1) |
N1—H2 | 1.001 (13) | C82—H821 | 1.10 (1) |
N1—O1i | 2.92 (1) | C82—H822 | 1.10 (1) |
N1—O2ii | 2.77 (1) | C82—H823 | 1.11 (1) |
C1—C2 | 1.44 (1) | C91—H911 | 1.10 (1) |
C1—C6 | 1.38 (1) | C91—H912 | 1.10 (1) |
C2—C3 | 1.39 (1) | C91—H913 | 1.10 (1) |
C3—C4 | 1.40 (1) | C92—H921 | 1.10 (1) |
C4—C5 | 1.38 (1) | C92—H922 | 1.10 (1) |
C5—C6 | 1.42 (1) | C92—H923 | 1.10 (1) |
O1—S1—O2 | 117 (1) | C6—C9—H9 | 104 (1) |
O1—S1—N1 | 109 (1) | C91—C9—H9 | 109 (1) |
C1—S1—O1 | 105 (1) | C92—C9—H9 | 109 (1) |
O2—S1—N1 | 108 (1) | C7—C71—H711 | 109 (1) |
C1—S1—O2 | 112 (1) | C7—C71—H712 | 109 (1) |
C1—S1—N1 | 105 (1) | C7—C71—H713 | 110 (1) |
S1—C1—C2 | 118 (1) | H711—C71—H712 | 110 (1) |
S1—C1—C6 | 120 (1) | H711—C71—H713 | 110 (1) |
C1—C2—C7 | 124 (1) | H712—C71—H713 | 109 (1) |
C3—C2—C7 | 118 (1) | C7—C72—H721 | 109 (1) |
C1—C6—C9 | 126 (1) | C7—C72—H722 | 109 (1) |
C5—C6—C9 | 114 (1) | C7—C72—H723 | 109 (1) |
C3—C4—C8 | 119 (1) | H721—C72—H722 | 110 (1) |
C5—C4—C8 | 119 (1) | H721—C72—H723 | 110 (1) |
C2—C7—C71 | 102 (1) | H722—C72—H723 | 109 (1) |
C2—C7—C72 | 112 (1) | C8—C81—H811 | 109 (1) |
C71—C7—C72 | 118 (1) | C8—C81—H812 | 109 (1) |
C4—C8—C81 | 110 (1) | C8—C81—H813 | 109 (1) |
C4—C8—C82 | 115 (1) | H811—C81—H812 | 110 (1) |
C81—C8—C82 | 108 (1) | H811—C81—H813 | 109 (1) |
C6—C9—C91 | 109 (1) | H812—C81—H813 | 110 (1) |
C6—C9—C92 | 113 (1) | C8—C82—H821 | 110 (1) |
C91—C9—C92 | 112 (1) | C8—C82—H822 | 109 (1) |
C2—C1—C6 | 122 (1) | C8—C82—H823 | 110 (1) |
C1—C2—C3 | 117 (1) | H821—C82—H822 | 110 (1) |
C2—C3—C4 | 121 (1) | H821—C82—H823 | 109 (1) |
C3—C4—C5 | 121 (1) | H822—C82—H823 | 109 (1) |
C4—C5—C6 | 119 (1) | C9—C91—H911 | 110 (1) |
C1—C6—C5 | 119 (1) | C9—C91—H912 | 110 (1) |
C2—C3—H3 | 120 (1) | C9—C91—H913 | 110 (1) |
C4—C3—H3 | 119 (1) | H911—C91—H912 | 109 (1) |
C4—C5—H5 | 121 (1) | H911—C91—H913 | 109 (1) |
C6—C5—H5 | 118 (1) | H912—C91—H913 | 109 (1) |
C2—C7—H7 | 104 (1) | C9—C92—H921 | 109 (1) |
C71—C7—H7 | 109 (1) | C9—C92—H922 | 110 (1) |
C72—C7—H7 | 109 (1) | C9—C92—H923 | 110 (1) |
C4—C8—H8 | 105 (1) | H921—C92—H922 | 110 (1) |
C81—C8—H8 | 109 (1) | H921—C92—H923 | 110 (1) |
C82—C8—H8 | 109 (1) | H922—C92—H923 | 111 (1) |
C1—C2—C7—C71 | −123 (1) | C1—C2—C7—C72 | 109 (1) |
C3—C4—C8—C81 | −113 (1) | C3—C4—C8—C82 | 124 (1) |
C1—C6—C9—C91 | −122 (1) | C1—C6—C9—C92 | 113 (1) |
C2—C1—S1—O1 | 59 (1) | C2—C1—S1—O2 | −172 (1) |
C2—C1—S1—N1 | −55 (1) |
Symmetry codes: (i) −x, −y+1, −z+1; (ii) −x, y+1/2, −z+3/2. |