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
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.004 Å
- R factor = 0.038
- wR factor = 0.088
- Data-to-parameter ratio = 13.7
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT165_ALERT_3_C Nr. of Status R Flagged Non-Hydrogen Atoms ..... 1 PLAT420_ALERT_2_C D-H Without Acceptor N1 - H1 ... ? PLAT480_ALERT_4_C Long H...A H-Bond Reported H5 .. CG1 .. 3.01 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H8 .. CG .. 2.83 Ang. PLAT751_ALERT_4_C Bond Calc 1.37996, Rep 1.380(3) ...... Senseless su C10 -C11 1.555 1.555 PLAT752_ALERT_4_C Angle Calc 112.48, Rep 112.48(16) ...... Senseless su C8 -C9 -C10 1.555 1.555 1.555 PLAT752_ALERT_4_C Angle Calc 112.05, Rep 112.05(15) ...... Senseless su C11 -C10 -C9 1.555 1.555 1.555 PLAT752_ALERT_4_C Angle Calc 127.20, Rep 127.2(3) ...... Senseless su C10 -C11 -C7 1.555 1.555 1.555 PLAT752_ALERT_4_C Angle Calc 111.37, Rep 111.4(2) ...... Senseless su C10 -C11 -S1 1.555 1.555 1.555
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 25.00 From the CIF: _reflns_number_total 1738 Count of symmetry unique reflns 1066 Completeness (_total/calc) 163.04% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 672 Fraction of Friedel pairs measured 0.630 Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 9 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 8 ALERT type 4 Improvement, methodology, query or suggestion
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. |