Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804019932/cv6354sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536804019932/cv6354Isup2.hkl |
CCDC reference: 251727
Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).
C11H10N2S | F(000) = 424 |
Mr = 202.27 | Dx = 1.334 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 12880 reflections |
a = 6.0473 (6) Å | θ = 1.8–25.8° |
b = 7.4417 (7) Å | µ = 0.28 mm−1 |
c = 22.376 (3) Å | T = 293 K |
V = 1006.97 (19) Å3 | Plate, colorless |
Z = 4 | 0.50 × 0.33 × 0.05 mm |
Stoe IPDS-2 diffractometer | 1738 independent reflections |
Radiation source: fine-focus sealed tube | 1403 reflections with I > 2σ(I) |
Plane graphite monochromator | Rint = 0.054 |
Detector resolution: 6.67 pixels mm-1 | θmax = 25.0°, θmin = 1.8° |
ω rotation scans | h = −6→7 |
Absorption correction: integration (X-RED; Stoe & Cie, 2002) | k = −8→8 |
Tmin = 0.892, Tmax = 0.986 | l = −26→26 |
5892 measured reflections |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.038 | H-atom parameters constrained |
wR(F2) = 0.088 | w = 1/[σ2(Fo2) + (0.052P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.93 | (Δ/σ)max = 0.001 |
1738 reflections | Δρmax = 0.37 e Å−3 |
127 parameters | Δρmin = −0.21 e Å−3 |
0 restraints | Absolute structure: (Flack, 1983) |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.03 (12) |
Experimental. Melting points were determined in open capillary tubes on a digital Gallenkamp melting point apparatus and are uncorrected. The IR spectra were recorded for KBr disks with a Mattson 1000 F T—IR spectrometer. 1H-NMR spectra were recorded on a FX 90 Jeol 90 MHz NMR, spectrometer in CDCl3 + DMSO-d6 with TMS as an internal standard. Elemental analyses were done on a LECO-CHNS-938. Starting materials was obtained from Fluka or Aldrich. For (I): IR (KBr) ?: 3325 (N—H), 3100,3087,3082, (aromatic C—H), 1603 (C=N), 1579,1535 (C=C). cm-1. 1H NMR (Aceton-d6) ?: 9.23(s, 1H, NH), 8.03(s, 1H, CH=), 7.48–6.63 (m 8H, Aromatic protons). 13 C NMR (Aceton- d6, TMS, ? p.p.m.): 146.20, 142.40, 133.06, 131.94, 129.87, 126.91, 126.17, 120.13, 113.37. Anal calcd for C11H10N2S: C: 65.35, H: 4.95, N: 13.88, S:15.84%. |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
S1 | 0.64972 (13) | 0.72536 (9) | 0.15971 (3) | 0.0366 (2) | |
N1 | 0.0542 (4) | 0.5413 (3) | 0.25417 (11) | 0.0322 (6) | |
H1 | −0.0396 | 0.4707 | 0.2373 | 0.039* | |
N2 | 0.2345 (4) | 0.5983 (3) | 0.22289 (11) | 0.0301 (6) | |
C1 | 0.0196 (5) | 0.5951 (3) | 0.31248 (12) | 0.0278 (6) | |
C2 | −0.1826 (5) | 0.5552 (3) | 0.33942 (13) | 0.0329 (7) | |
H2 | −0.2926 | 0.4971 | 0.3177 | 0.040* | |
C3 | −0.2192 (5) | 0.6017 (4) | 0.39798 (14) | 0.0379 (7) | |
H3 | −0.3534 | 0.5732 | 0.4159 | 0.045* | |
C4 | −0.0575 (6) | 0.6911 (4) | 0.43083 (13) | 0.0387 (8) | |
H4 | −0.0825 | 0.7224 | 0.4705 | 0.046* | |
C5 | 0.1417 (5) | 0.7328 (4) | 0.40332 (11) | 0.0356 (6) | |
H5 | 0.2503 | 0.7928 | 0.4250 | 0.043* | |
C6 | 0.1818 (5) | 0.6876 (3) | 0.34499 (13) | 0.0303 (6) | |
H6 | 0.3155 | 0.7180 | 0.3271 | 0.036* | |
C7 | 0.2451 (5) | 0.5545 (3) | 0.16801 (13) | 0.0301 (7) | |
H7 | 0.1329 | 0.4848 | 0.1516 | 0.036* | |
C8 | 0.7673 (5) | 0.7451 (4) | 0.09058 (12) | 0.0384 (7) | |
H8 | 0.9016 | 0.8023 | 0.0836 | 0.046* | |
C9 | 0.6436 (4) | 0.6683 (2) | 0.04706 (9) | 0.0370 (7) | |
H9 | 0.6836 | 0.6668 | 0.0069 | 0.044* | |
C10 | 0.4461 (4) | 0.5902 (2) | 0.06955 (9) | 0.0314 (7) | |
H10 | 0.3417 | 0.5323 | 0.0459 | 0.038* | |
C11 | 0.4273 (5) | 0.6105 (3) | 0.13064 (12) | 0.0294 (7) |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0331 (4) | 0.0346 (4) | 0.0422 (4) | −0.0028 (3) | −0.0035 (4) | −0.0039 (3) |
N1 | 0.0283 (16) | 0.0303 (13) | 0.0379 (13) | −0.0091 (11) | −0.0024 (12) | −0.0024 (10) |
N2 | 0.0285 (14) | 0.0273 (12) | 0.0345 (13) | 0.0008 (10) | −0.0029 (11) | 0.0034 (10) |
C1 | 0.0254 (17) | 0.0209 (13) | 0.0370 (16) | 0.0006 (12) | −0.0022 (12) | 0.0055 (11) |
C2 | 0.0256 (17) | 0.0298 (14) | 0.0435 (16) | 0.0001 (12) | −0.0033 (15) | 0.0051 (13) |
C3 | 0.0305 (19) | 0.0356 (17) | 0.0476 (18) | 0.0028 (14) | 0.0076 (14) | 0.0130 (14) |
C4 | 0.052 (2) | 0.0329 (16) | 0.0315 (15) | 0.0116 (15) | 0.0020 (14) | 0.0027 (13) |
C5 | 0.0407 (17) | 0.0275 (15) | 0.0385 (14) | −0.0023 (17) | −0.0102 (15) | 0.0018 (12) |
C6 | 0.0220 (16) | 0.0252 (13) | 0.0436 (16) | 0.0001 (11) | −0.0030 (14) | 0.0048 (12) |
C7 | 0.0272 (15) | 0.0236 (13) | 0.0395 (18) | 0.0014 (11) | −0.0054 (13) | 0.0017 (12) |
C8 | 0.0390 (17) | 0.0259 (16) | 0.0502 (18) | 0.0023 (14) | 0.0050 (13) | 0.0002 (13) |
C9 | 0.043 (2) | 0.0307 (15) | 0.0374 (15) | −0.0015 (16) | 0.0028 (17) | 0.0003 (12) |
C10 | 0.0329 (18) | 0.0266 (14) | 0.0348 (15) | 0.0020 (14) | −0.0033 (13) | 0.0032 (12) |
C11 | 0.0312 (18) | 0.0180 (13) | 0.0390 (16) | 0.0023 (12) | −0.0047 (13) | 0.0022 (11) |
S1—C8 | 1.709 (3) | C4—H4 | 0.9300 |
S1—C11 | 1.721 (3) | C5—C6 | 1.369 (4) |
N1—N2 | 1.363 (3) | C5—H5 | 0.9300 |
N1—C1 | 1.381 (4) | C6—H6 | 0.9300 |
N1—H1 | 0.8600 | C7—C11 | 1.445 (4) |
N2—C7 | 1.272 (4) | C7—H7 | 0.9300 |
C1—C2 | 1.395 (4) | C8—C9 | 1.354 (4) |
C1—C6 | 1.402 (4) | C8—H8 | 0.9300 |
C2—C3 | 1.373 (4) | C9—C10 | 1.4205 |
C2—H2 | 0.9300 | C9—H9 | 0.9300 |
C3—C4 | 1.393 (4) | C10—C11 | 1.380 (3) |
C3—H3 | 0.9300 | C10—H10 | 0.9300 |
C4—C5 | 1.388 (4) | ||
C8—S1—C11 | 91.48 (14) | C4—C5—H5 | 119.3 |
N2—N1—C1 | 121.1 (2) | C5—C6—C1 | 119.4 (3) |
N2—N1—H1 | 119.5 | C5—C6—H6 | 120.3 |
C1—N1—H1 | 119.5 | C1—C6—H6 | 120.3 |
C7—N2—N1 | 117.1 (2) | N2—C7—C11 | 121.6 (3) |
N1—C1—C2 | 118.6 (3) | N2—C7—H7 | 119.2 |
N1—C1—C6 | 121.8 (3) | C11—C7—H7 | 119.2 |
C2—C1—C6 | 119.6 (3) | C9—C8—S1 | 112.6 (2) |
C3—C2—C1 | 120.0 (3) | C9—C8—H8 | 123.7 |
C3—C2—H2 | 120.0 | S1—C8—H8 | 123.7 |
C1—C2—H2 | 120.0 | C8—C9—C10 | 112.48 (16) |
C2—C3—C4 | 120.7 (3) | C8—C9—H9 | 123.8 |
C2—C3—H3 | 119.6 | C10—C9—H9 | 123.8 |
C4—C3—H3 | 119.6 | C11—C10—C9 | 112.05 (15) |
C5—C4—C3 | 118.8 (3) | C11—C10—H10 | 124.0 |
C5—C4—H4 | 120.6 | C9—C10—H10 | 124.0 |
C3—C4—H4 | 120.6 | C10—C11—C7 | 127.2 (3) |
C6—C5—C4 | 121.4 (3) | C10—C11—S1 | 111.4 (2) |
C6—C5—H5 | 119.3 | C7—C11—S1 | 121.4 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
C5—H5···Cg1i | 0.93 | 3.01 | 3.631 (3) | 126 |
C7—H7···Cgii | 0.93 | 2.68 | 3.461 (3) | 142 |
C8—H8···Cgi | 0.93 | 2.83 | 3.443 (3) | 125 |
Symmetry codes: (i) −x+1, y+1/2, −z+1/2; (ii) −x, y−1/2, −z+1/2. |