Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804016551/lh6236sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536804016551/lh6236IIIsup2.hkl |
CCDC reference: 248800
Key indicators
- Single-crystal X-ray study
- T = 150 K
- Mean (C-C) = 0.004 Å
- R factor = 0.054
- wR factor = 0.148
- Data-to-parameter ratio = 13.8
checkCIF/PLATON results
No syntax errors found
Alert level C RINTA01_ALERT_3_C The value of Rint is greater than 0.10 Rint given 0.143 PLAT020_ALERT_3_C The value of Rint is greater than 0.10 ......... 0.14 PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 1 C15 H13 N3 O S
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED32 (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) and PLATON (Spek, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).
C15H13N3OS | F(000) = 1184 |
Mr = 283.34 | Dx = 1.410 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -C 2yc | Cell parameters from 10560 reflections |
a = 26.524 (3) Å | θ = 1.6–27.2° |
b = 11.3288 (18) Å | µ = 0.24 mm−1 |
c = 9.2310 (11) Å | T = 150 K |
β = 104.643 (9)° | Plate, colourless |
V = 2683.7 (6) Å3 | 0.38 × 0.26 × 0.08 mm |
Z = 8 |
Stoe IPDS 2 diffractometer | 2636 independent reflections |
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus | 1775 reflections with I > 2σ(I) |
Plane graphite monochromator | Rint = 0.143 |
Detector resolution: 6.67 pixels mm-1 | θmax = 26.0°, θmin = 1.6° |
rotation method scans | h = −32→32 |
Absorption correction: integration (X-RED32; Stoe & Cie, 2002) | k = −13→13 |
Tmin = 0.919, Tmax = 0.978 | l = −11→11 |
9354 measured reflections |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.054 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.148 | H-atom parameters constrained |
S = 0.98 | w = 1/[σ2(Fo2) + (0.0749P)2] where P = (Fo2 + 2Fc2)/3 |
2636 reflections | (Δ/σ)max = 0.001 |
191 parameters | Δρmax = 0.41 e Å−3 |
0 restraints | Δρmin = −0.60 e Å−3 |
Experimental. Melting points were determined in open capillary tubes on a Gallenkamp digital melting-point apparatus and are uncorrected. The IR spectra were recorded as KBr disks with a Mattson 1000 F T—IR spectrometer. 1H NMR spectra were recorded on an FX 90 Jeol 90 MHz NMR spectrometer in DMSO-d6 with TMS as an internal standard. |
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 | 0.01200 (2) | 0.69821 (7) | 0.02543 (9) | 0.0327 (3) | |
O1 | 0.15575 (7) | 0.41156 (17) | −0.3164 (2) | 0.0368 (6) | |
H1 | 0.1382 | 0.4075 | −0.2551 | 0.055* | |
N1 | 0.09264 (7) | 0.69074 (19) | −0.1113 (3) | 0.0261 (6) | |
N2 | 0.09765 (8) | 0.5010 (2) | −0.1596 (3) | 0.0319 (6) | |
N3 | 0.05803 (8) | 0.5225 (2) | −0.0939 (3) | 0.0324 (6) | |
H3 | 0.0377 | 0.4683 | −0.0759 | 0.039* | |
C1 | 0.17960 (9) | 0.5179 (3) | −0.3051 (3) | 0.0299 (7) | |
C2 | 0.22122 (9) | 0.5277 (3) | −0.3695 (4) | 0.0343 (7) | |
H2 | 0.2305 | 0.4634 | −0.4199 | 0.041* | |
C3 | 0.24902 (9) | 0.6307 (3) | −0.3601 (4) | 0.0362 (8) | |
H3A | 0.2770 | 0.6357 | −0.4035 | 0.043* | |
C4 | 0.23540 (9) | 0.7272 (3) | −0.2859 (4) | 0.0368 (8) | |
H4 | 0.2546 | 0.7968 | −0.2776 | 0.044* | |
C5 | 0.19327 (9) | 0.7195 (3) | −0.2244 (4) | 0.0332 (7) | |
H5 | 0.1842 | 0.7851 | −0.1760 | 0.040* | |
C6 | 0.16385 (9) | 0.6166 (3) | −0.2325 (3) | 0.0267 (6) | |
C7 | 0.11891 (9) | 0.6040 (2) | −0.1687 (3) | 0.0266 (6) | |
C8 | 0.05382 (9) | 0.6361 (2) | −0.0602 (3) | 0.0269 (7) | |
C9 | 0.09922 (9) | 0.8174 (2) | −0.1062 (3) | 0.0250 (6) | |
C10 | 0.13459 (9) | 0.8698 (3) | 0.0140 (3) | 0.0295 (7) | |
H10 | 0.1548 | 0.8238 | 0.0904 | 0.035* | |
C11 | 0.13906 (10) | 0.9907 (3) | 0.0177 (3) | 0.0316 (7) | |
H11 | 0.1633 | 1.0261 | 0.0963 | 0.038* | |
C12 | 0.10809 (9) | 1.0616 (3) | −0.0934 (3) | 0.0291 (7) | |
C13 | 0.07306 (10) | 1.0065 (3) | −0.2112 (4) | 0.0330 (7) | |
H13 | 0.0523 | 1.0522 | −0.2869 | 0.040* | |
C14 | 0.06843 (9) | 0.8848 (3) | −0.2182 (4) | 0.0317 (7) | |
H14 | 0.0447 | 0.8490 | −0.2977 | 0.038* | |
C15 | 0.11145 (10) | 1.1944 (3) | −0.0873 (4) | 0.0387 (8) | |
H15A | 0.1003 | 1.2224 | −0.0023 | 0.058* | |
H15B | 0.0894 | 1.2269 | −0.1772 | 0.058* | |
H15C | 0.1468 | 1.2184 | −0.0785 | 0.058* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0210 (3) | 0.0297 (5) | 0.0499 (6) | −0.0004 (3) | 0.0139 (3) | 0.0015 (4) |
O1 | 0.0296 (9) | 0.0327 (12) | 0.0510 (15) | −0.0052 (8) | 0.0156 (9) | −0.0063 (11) |
N1 | 0.0184 (9) | 0.0244 (12) | 0.0357 (15) | −0.0015 (8) | 0.0074 (9) | 0.0000 (11) |
N2 | 0.0207 (10) | 0.0300 (14) | 0.0469 (17) | −0.0030 (9) | 0.0123 (10) | −0.0032 (12) |
N3 | 0.0204 (10) | 0.0274 (13) | 0.0522 (18) | −0.0048 (9) | 0.0146 (10) | 0.0017 (12) |
C1 | 0.0197 (11) | 0.0337 (16) | 0.0334 (18) | −0.0001 (11) | 0.0016 (11) | −0.0023 (13) |
C2 | 0.0234 (12) | 0.0391 (18) | 0.0403 (19) | 0.0030 (12) | 0.0079 (11) | −0.0040 (15) |
C3 | 0.0201 (12) | 0.052 (2) | 0.039 (2) | 0.0008 (12) | 0.0113 (11) | 0.0013 (15) |
C4 | 0.0229 (13) | 0.0407 (18) | 0.048 (2) | −0.0076 (12) | 0.0104 (12) | 0.0007 (16) |
C5 | 0.0256 (13) | 0.0326 (17) | 0.042 (2) | −0.0034 (11) | 0.0095 (12) | −0.0064 (14) |
C6 | 0.0191 (11) | 0.0317 (15) | 0.0289 (17) | −0.0006 (11) | 0.0055 (10) | 0.0011 (13) |
C7 | 0.0193 (11) | 0.0271 (15) | 0.0317 (17) | −0.0001 (10) | 0.0032 (10) | −0.0032 (13) |
C8 | 0.0183 (11) | 0.0285 (15) | 0.0326 (18) | −0.0035 (10) | 0.0038 (10) | 0.0033 (13) |
C9 | 0.0187 (11) | 0.0254 (14) | 0.0322 (17) | −0.0008 (10) | 0.0086 (10) | 0.0003 (13) |
C10 | 0.0233 (12) | 0.0308 (16) | 0.0322 (18) | −0.0002 (10) | 0.0028 (11) | 0.0026 (13) |
C11 | 0.0232 (12) | 0.0354 (17) | 0.0342 (18) | −0.0048 (11) | 0.0038 (11) | −0.0050 (14) |
C12 | 0.0216 (11) | 0.0284 (15) | 0.0400 (19) | −0.0005 (11) | 0.0126 (11) | −0.0015 (13) |
C13 | 0.0214 (11) | 0.0345 (17) | 0.041 (2) | 0.0016 (11) | 0.0039 (12) | 0.0075 (15) |
C14 | 0.0171 (11) | 0.0380 (17) | 0.0374 (19) | −0.0035 (11) | 0.0024 (11) | −0.0001 (14) |
C15 | 0.0268 (13) | 0.0313 (17) | 0.058 (2) | 0.0006 (11) | 0.0116 (13) | −0.0009 (15) |
S1—C8 | 1.671 (3) | C5—C6 | 1.395 (4) |
O1—C1 | 1.353 (3) | C5—H5 | 0.9300 |
O1—H1 | 0.8200 | C6—C7 | 1.464 (4) |
N1—C8 | 1.382 (3) | C9—C14 | 1.376 (4) |
N1—C7 | 1.385 (3) | C9—C10 | 1.392 (4) |
N1—C9 | 1.445 (3) | C10—C11 | 1.374 (4) |
N2—C7 | 1.308 (3) | C10—H10 | 0.9300 |
N2—N3 | 1.361 (3) | C11—C12 | 1.396 (4) |
N3—C8 | 1.335 (4) | C11—H11 | 0.9300 |
N3—H3 | 0.8600 | C12—C13 | 1.387 (4) |
C1—C2 | 1.384 (4) | C12—C15 | 1.507 (4) |
C1—C6 | 1.420 (4) | C13—C14 | 1.384 (4) |
C2—C3 | 1.371 (4) | C13—H13 | 0.9300 |
C2—H2 | 0.9300 | C14—H14 | 0.9300 |
C3—C4 | 1.387 (4) | C15—H15A | 0.9600 |
C3—H3A | 0.9300 | C15—H15B | 0.9600 |
C4—C5 | 1.378 (4) | C15—H15C | 0.9600 |
C4—H4 | 0.9300 | ||
C1—O1—H1 | 109.5 | N1—C7—C6 | 128.6 (2) |
C8—N1—C7 | 107.6 (2) | N3—C8—N1 | 103.8 (2) |
C8—N1—C9 | 121.8 (2) | N3—C8—S1 | 128.4 (2) |
C7—N1—C9 | 130.5 (2) | N1—C8—S1 | 127.9 (2) |
C7—N2—N3 | 105.2 (2) | C14—C9—C10 | 121.0 (3) |
C8—N3—N2 | 113.3 (2) | C14—C9—N1 | 118.9 (2) |
C8—N3—H3 | 123.3 | C10—C9—N1 | 120.1 (2) |
N2—N3—H3 | 123.3 | C11—C10—C9 | 118.8 (3) |
O1—C1—C2 | 116.5 (3) | C11—C10—H10 | 120.6 |
O1—C1—C6 | 123.4 (2) | C9—C10—H10 | 120.6 |
C2—C1—C6 | 120.1 (3) | C10—C11—C12 | 121.7 (3) |
C3—C2—C1 | 121.0 (3) | C10—C11—H11 | 119.2 |
C3—C2—H2 | 119.5 | C12—C11—H11 | 119.2 |
C1—C2—H2 | 119.5 | C13—C12—C11 | 118.0 (3) |
C2—C3—C4 | 120.0 (3) | C13—C12—C15 | 120.0 (3) |
C2—C3—H3A | 120.0 | C11—C12—C15 | 122.0 (3) |
C4—C3—H3A | 120.0 | C14—C13—C12 | 121.2 (3) |
C5—C4—C3 | 119.5 (3) | C14—C13—H13 | 119.4 |
C5—C4—H4 | 120.2 | C12—C13—H13 | 119.4 |
C3—C4—H4 | 120.2 | C9—C14—C13 | 119.3 (3) |
C4—C5—C6 | 122.2 (3) | C9—C14—H14 | 120.3 |
C4—C5—H5 | 118.9 | C13—C14—H14 | 120.3 |
C6—C5—H5 | 118.9 | C12—C15—H15A | 109.5 |
C5—C6—C1 | 117.1 (2) | C12—C15—H15B | 109.5 |
C5—C6—C7 | 124.2 (3) | H15A—C15—H15B | 109.5 |
C1—C6—C7 | 118.7 (2) | C12—C15—H15C | 109.5 |
N2—C7—N1 | 110.0 (2) | H15A—C15—H15C | 109.5 |
N2—C7—C6 | 121.4 (2) | H15B—C15—H15C | 109.5 |
C7—N2—N3—C8 | −0.5 (3) | C1—C6—C7—N1 | −170.7 (3) |
O1—C1—C2—C3 | −177.9 (3) | N2—N3—C8—N1 | 1.5 (3) |
C6—C1—C2—C3 | 2.3 (4) | N2—N3—C8—S1 | −177.9 (2) |
C1—C2—C3—C4 | −0.3 (4) | C7—N1—C8—N3 | −1.9 (3) |
C2—C3—C4—C5 | −1.2 (4) | C9—N1—C8—N3 | 175.5 (2) |
C3—C4—C5—C6 | 0.8 (5) | C7—N1—C8—S1 | 177.5 (2) |
C4—C5—C6—C1 | 1.1 (4) | C9—N1—C8—S1 | −5.1 (4) |
C4—C5—C6—C7 | 179.8 (3) | C8—N1—C9—C14 | −82.1 (3) |
O1—C1—C6—C5 | 177.6 (3) | C7—N1—C9—C14 | 94.6 (3) |
C2—C1—C6—C5 | −2.6 (4) | C8—N1—C9—C10 | 95.0 (3) |
O1—C1—C6—C7 | −1.2 (4) | C7—N1—C9—C10 | −88.2 (4) |
C2—C1—C6—C7 | 178.6 (2) | C14—C9—C10—C11 | −1.3 (4) |
N3—N2—C7—N1 | −0.8 (3) | N1—C9—C10—C11 | −178.4 (2) |
N3—N2—C7—C6 | 179.3 (2) | C9—C10—C11—C12 | 1.8 (4) |
C8—N1—C7—N2 | 1.8 (3) | C10—C11—C12—C13 | −1.5 (4) |
C9—N1—C7—N2 | −175.3 (3) | C10—C11—C12—C15 | 177.8 (3) |
C8—N1—C7—C6 | −178.3 (3) | C11—C12—C13—C14 | 0.6 (4) |
C9—N1—C7—C6 | 4.6 (5) | C15—C12—C13—C14 | −178.7 (3) |
C5—C6—C7—N2 | −169.5 (3) | C10—C9—C14—C13 | 0.4 (4) |
C1—C6—C7—N2 | 9.2 (4) | N1—C9—C14—C13 | 177.6 (3) |
C5—C6—C7—N1 | 10.6 (4) | C12—C13—C14—C9 | −0.1 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3···S1i | 0.86 | 2.41 | 3.271 (3) | 174 |
C14—H14···S1ii | 0.93 | 2.83 | 3.742 (3) | 168 |
O1—H1···N2 | 0.82 | 1.88 | 2.574 (3) | 142 |
Symmetry codes: (i) −x, −y+1, −z; (ii) −x, y, −z−1/2. |
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