2,4,6-Triisopropylbenzenesulfonamide: Monte Carlo structure solution from X-ray powder diffraction data for a molecular system containing four independent asymmetric rotors

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 and rings.

Computing details

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

Crystal data

C15H25NO2S	V = 1572.3 (1) Å^3
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

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

Rp = 0.050	143 parameters
Rwp = 0.071	120 restraints
R(F^2) = 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 (Ų)

	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)

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—O1^i	2.92 (1)	C82—H822	1.10 (1)
N1—O2^ii	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.