Download citation
Download citation
link to html
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.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108768110039327/zb5014sup1.cif
Contains datablock LC_publ

rtv

Rietveld powder data file (CIF format) https://doi.org/10.1107/S0108768110039327/zb5014Isup2.rtv
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768110039327/zb5014Isup3.hkl
Contains datablock I

CCDC reference: 801339

Computing details top

Program(s) used to refine structure: GSAS.

(LC_publ) top
Crystal data top
C11H13N3O2S2V = 2740.91 Å3
Mr = 283.26Z = 8
Orthorhombic, PbcaCu Kα1 radiation, λ = 1.5406 Å
a = 8.5364 (2) ÅT = 293 K
b = 15.0148 (3) Åwhite
c = 21.3846 (3) Åflat_sheet, 25 × 1 mm
Data collection top
Bruker D8 Advance
diffractometer
Data collection mode: reflection
Ge(111) monochromatorScan method: continuous
Specimen mounting: Bruker sample cup2θmin = 3.542°, 2θmax = 50.027°, 2θstep = 0.005°
Refinement top
Least-squares matrix: fullProfile 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 = 0.07956 parameters
Rwp = 0.11348 restraints
Rexp = 0.053H-atom parameters not defined?
R(F2) = 0.10350(Δ/σ)max = 1.02
9298 data pointsBackground 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 (Å2) top
xyzUiso*/Ueq
C10.1494 (9)0.3598 (5)0.1675 (4)0.0437 (5)*
C20.2652 (7)0.2953 (5)0.1919 (4)0.0437 (5)*
C30.1882 (7)0.2023 (4)0.2006 (3)0.0437 (5)*
N10.2288 (7)0.1448 (4)0.2437 (3)0.0437 (5)*
N20.1375 (8)0.0695 (4)0.2453 (3)0.0437 (5)*
C40.0539 (8)0.0622 (4)0.1942 (3)0.0437 (5)*
S10.0643 (4)0.1530 (2)0.14528 (14)0.0437 (5)*
N30.0284 (7)0.0166 (4)0.1821 (3)0.0437 (5)*
S20.1586 (3)0.03055 (19)0.12623 (14)0.0437 (5)*
O10.3206 (7)0.0376 (4)0.1499 (3)0.0437 (5)*
O20.1237 (7)0.0354 (4)0.0794 (3)0.0437 (5)*
C50.0923 (2)0.1366 (3)0.0950 (3)0.0437 (5)*
C60.1500 (7)0.2170 (4)0.1218 (3)0.0437 (5)*
C70.09996 (10)0.29974 (6)0.0991 (3)0.0437 (5)*
C80.0000 (7)0.30218 (6)0.04590 (4)0.0437 (5)*
C100.0160 (7)0.1399 (4)0.04586 (8)0.0437 (5)*
C90.0635 (7)0.2209 (4)0.02109 (10)0.0437 (5)*
C110.0565 (9)0.3910 (5)0.0197 (4)0.0437 (5)*
Geometric parameters (Å, º) top
C1—C21.479 (10)S2—O11.476 (7)
C2—C11.479 (10)S2—O21.439 (7)
C2—C31.555 (9)S2—C51.817 (5)
C3—C21.555 (9)O1—S21.476 (7)
C3—N11.309 (8)O2—S21.439 (7)
C3—S11.751 (6)C5—S21.817 (5)
N1—C31.309 (8)C5—C61.425 (8)
N1—N21.373 (8)C5—C101.400 (6)
N1—S12.534 (6)C6—C51.425 (8)
N2—N11.373 (8)C6—C71.401 (7)
N2—C41.310 (8)C7—C61.401 (7)
C4—N21.310 (8)C7—C81.422 (6)
C4—S11.721 (6)C8—C71.422 (6)
C4—N31.400 (8)C8—C91.437 (6)
S1—C31.751 (6)C8—C111.525 (8)
S1—N12.534 (6)C10—C51.400 (6)
S1—C41.721 (6)C10—C91.387 (8)
N3—C41.400 (8)C9—C81.437 (6)
N3—S21.645 (7)C9—C101.387 (8)
S2—N31.645 (7)C11—C81.525 (8)
C1—C2—C3110.3 (5)O1—S2—O2118.8 (4)
C2—C3—N1124.4 (5)O1—S2—C5110.8 (3)
C2—C3—S1123.6 (4)O2—S2—C5106.4 (3)
N1—C3—S1110.9 (4)S2—C5—C6119.1 (4)
C3—N1—N2114.2 (5)S2—C5—C10120.9 (4)
N1—N2—C4111.0 (5)C6—C5—C10120.0 (5)
N2—C4—S1114.4 (5)C5—C6—C7120.4 (5)
N2—C4—N3119.9 (5)C6—C7—C8118.9 (3)
S1—C4—N3125.6 (4)C7—C8—C9120.0 (2)
C3—S1—C487.4 (3)C7—C8—C11120.4 (3)
C4—N3—S2125.5 (5)C9—C8—C11119.2 (4)
N3—S2—O1113.1 (4)C5—C10—C9120.7 (5)
N3—S2—O2106.1 (4)C8—C9—C10119.6 (4)
N3—S2—C599.7 (3)
 

Follow Acta Cryst. B
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds