Structure of N-(5-ethyl-[1,3,4]-thiadiazole-2-yl)­toluenesulfonamide by combined X-ray powder diffraction, ¹³C solid-state NMR and molecular modelling

The crystal structure solution of the title compound is determined from microcrystalline powder using a multi-technique approach that combines X-ray powder diffraction (XRPD) data analysis based on direct-space methods with information from ¹³C solid-state NMR (SSNMR), and molecular modelling using the GIPAW (gauge including projector augmented-wave) method. The space group is Pbca with one molecule in the asymmetric unit. The proposed methodology proves very useful for unambiguously characterizing the supramolecular arrangement adopted by the N-(5-ethyl-[1,3,4]-thiadiazole-2-yl)toluenesulfonamide molecules in the crystal, which consists of extended double strands held together by C—H...π non-covalent interactions.

Computing details

Program(s) used to refine structure: GSAS.

(LC_publ)

Crystal data

C11H13N3O2S2	V = 2740.91 Å^3
Mr = 283.26	Z = 8
Orthorhombic, Pbca	Cu Kα1 radiation, λ = 1.5406 Å
a = 8.5364 (2) Å	T = 293 K
b = 15.0148 (3) Å	white
c = 21.3846 (3) Å	flat_sheet, 25 × 1 mm

Data collection

Bruker D8 Advance diffractometer	Data collection mode: reflection
Ge(111) monochromator	Scan method: continuous
Specimen mounting: Bruker sample cup	2θmin = 3.542°, 2θmax = 50.027°, 2θstep = 0.005°

Refinement

Least-squares matrix: full	Profile function: CW Profile function number 4 with 18 terms Pseudovoigt profile coefficients as parameterized in P. Thompson, D.E. Cox & J.B. Hastings (1987). J. Appl. Cryst.,20,79-83. Asymmetry correction of L.W. Finger, D.E. Cox & A. P. Jephcoat (1994). J. Appl. Cryst.,27,892-900. Microstrain broadening by P.W. Stephens, (1999). J. Appl. Cryst.,32,281-289. #1(GU) = 345.855 #2(GV) = -46.144 #3(GW) = 3.804 #4(GP) = 5.633 #5(LX) = 0.048 #6(ptec) = 0.00 #7(trns) = 0.00 #8(shft) = -0.5224 #9(sfec) = 0.00 #10(S/L) = 0.0179 #11(H/L) = 0.0182 #12(eta) = 0.7500 #13(S400 ) = 0.0E+00 #14(S040 ) = 0.0E+00 #15(S004 ) = 0.0E+00 #16(S220 ) = 0.0E+00 #17(S202 ) = 0.0E+00 #18(S022 ) = 0.0E+00 Peak tails are ignored where the intensity is below 0.0100 times the peak Aniso. broadening axis 0.0 0.0 1.0
Rp = 0.079	56 parameters
Rwp = 0.113	48 restraints
Rexp = 0.053	H-atom parameters not defined?
R(F^2) = 0.10350	(Δ/σ)max = 1.02
9298 data points	Background function: GSAS Background function number 1 with 13 terms. Shifted Chebyshev function of 1st kind 1: 234.111 2: -260.100 3: 131.588 4: -55.7401 5: 25.3514 6: -3.00434 7: -4.08634 8: 13.0009 9: -2.47133 10: -1.75930 11: 1.47926 12: -3.75949 13: 0.912415

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C1	0.1494 (9)	−0.3598 (5)	0.1675 (4)	0.0437 (5)*
C2	0.2652 (7)	−0.2953 (5)	0.1919 (4)	0.0437 (5)*
C3	0.1882 (7)	−0.2023 (4)	0.2006 (3)	0.0437 (5)*
N1	0.2288 (7)	−0.1448 (4)	0.2437 (3)	0.0437 (5)*
N2	0.1375 (8)	−0.0695 (4)	0.2453 (3)	0.0437 (5)*
C4	0.0539 (8)	−0.0622 (4)	0.1942 (3)	0.0437 (5)*
S1	0.0643 (4)	−0.1530 (2)	0.14528 (14)	0.0437 (5)*
N3	−0.0284 (7)	0.0166 (4)	0.1821 (3)	0.0437 (5)*
S2	−0.1586 (3)	0.03055 (19)	0.12623 (14)	0.0437 (5)*
O1	−0.3206 (7)	0.0376 (4)	0.1499 (3)	0.0437 (5)*
O2	−0.1237 (7)	−0.0354 (4)	0.0794 (3)	0.0437 (5)*
C5	−0.0923 (2)	0.1366 (3)	0.0950 (3)	0.0437 (5)*
C6	−0.1500 (7)	0.2170 (4)	0.1218 (3)	0.0437 (5)*
C7	−0.09996 (10)	0.29974 (6)	0.0991 (3)	0.0437 (5)*
C8	0.0000 (7)	0.30218 (6)	0.04590 (4)	0.0437 (5)*
C10	0.0160 (7)	0.1399 (4)	0.04586 (8)	0.0437 (5)*
C9	0.0635 (7)	0.2209 (4)	0.02109 (10)	0.0437 (5)*
C11	0.0565 (9)	0.3910 (5)	0.0197 (4)	0.0437 (5)*

Geometric parameters (Å, º)

C1—C2	1.479 (10)	S2—O1	1.476 (7)
C2—C1	1.479 (10)	S2—O2	1.439 (7)
C2—C3	1.555 (9)	S2—C5	1.817 (5)
C3—C2	1.555 (9)	O1—S2	1.476 (7)
C3—N1	1.309 (8)	O2—S2	1.439 (7)
C3—S1	1.751 (6)	C5—S2	1.817 (5)
N1—C3	1.309 (8)	C5—C6	1.425 (8)
N1—N2	1.373 (8)	C5—C10	1.400 (6)
N1—S1	2.534 (6)	C6—C5	1.425 (8)
N2—N1	1.373 (8)	C6—C7	1.401 (7)
N2—C4	1.310 (8)	C7—C6	1.401 (7)
C4—N2	1.310 (8)	C7—C8	1.422 (6)
C4—S1	1.721 (6)	C8—C7	1.422 (6)
C4—N3	1.400 (8)	C8—C9	1.437 (6)
S1—C3	1.751 (6)	C8—C11	1.525 (8)
S1—N1	2.534 (6)	C10—C5	1.400 (6)
S1—C4	1.721 (6)	C10—C9	1.387 (8)
N3—C4	1.400 (8)	C9—C8	1.437 (6)
N3—S2	1.645 (7)	C9—C10	1.387 (8)
S2—N3	1.645 (7)	C11—C8	1.525 (8)
C1—C2—C3	110.3 (5)	O1—S2—O2	118.8 (4)
C2—C3—N1	124.4 (5)	O1—S2—C5	110.8 (3)
C2—C3—S1	123.6 (4)	O2—S2—C5	106.4 (3)
N1—C3—S1	110.9 (4)	S2—C5—C6	119.1 (4)
C3—N1—N2	114.2 (5)	S2—C5—C10	120.9 (4)
N1—N2—C4	111.0 (5)	C6—C5—C10	120.0 (5)
N2—C4—S1	114.4 (5)	C5—C6—C7	120.4 (5)
N2—C4—N3	119.9 (5)	C6—C7—C8	118.9 (3)
S1—C4—N3	125.6 (4)	C7—C8—C9	120.0 (2)
C3—S1—C4	87.4 (3)	C7—C8—C11	120.4 (3)
C4—N3—S2	125.5 (5)	C9—C8—C11	119.2 (4)
N3—S2—O1	113.1 (4)	C5—C10—C9	120.7 (5)
N3—S2—O2	106.1 (4)	C8—C9—C10	119.6 (4)
N3—S2—C5	99.7 (3)