Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806010610/at2018sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806010610/at2018Isup2.hkl |
CCDC reference: 604958
Key indicators
- Single-crystal X-ray study
- T = 296 K
- Mean (C-C) = 0.009 Å
- R factor = 0.068
- wR factor = 0.187
- Data-to-parameter ratio = 8.1
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.05 PLAT128_ALERT_4_C Non-standard setting of Space group Pna21 .... Pn21a PLAT322_ALERT_2_C Check Hybridisation of S1 in Main Residue . ? PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 9
Alert level G REFLT03_ALERT_4_G WARNING: Large fraction of Friedel related reflns may be needed to determine absolute structure From the CIF: _diffrn_reflns_theta_max 70.76 From the CIF: _reflns_number_total 1034 Count of symmetry unique reflns 1034 Completeness (_total/calc) 100.00% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 0 Fraction of Friedel pairs measured 0.000 Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 4 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 2 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 2 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995); 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).
C10H10N2OS | F(000) = 432 |
Mr = 206.26 | Dx = 1.368 Mg m−3 |
Orthorhombic, Pn21a | Cu Kα radiation, λ = 1.54184 Å |
Hall symbol: P -2ac -2n | Cell parameters from 25 reflections |
a = 7.181 (2) Å | θ = 2.6–28.3° |
b = 7.750 (2) Å | µ = 2.61 mm−1 |
c = 17.994 (3) Å | T = 296 K |
V = 1001.4 (4) Å3 | Plate, colorless |
Z = 4 | 0.35 × 0.25 × 0.10 mm |
Enraf–Nonius TurboCAD-4 diffractometer | 847 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.000 |
Graphite monochromator | θmax = 70.8°, θmin = 4.9° |
Non–profiled ω scans | h = 0→8 |
Absorption correction: ψ scan (North et al., 1968) | k = 0→9 |
Tmin = 0.475, Tmax = 0.768 | l = −22→0 |
1034 measured reflections | 3 standard reflections every 120 min |
1034 independent reflections | intensity decay: 1% |
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)] = 0.068 | H-atom parameters constrained |
wR(F2) = 0.187 | w = 1/[σ2(Fo2) + (0.1346P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | (Δ/σ)max < 0.001 |
1034 reflections | Δρmax = 0.65 e Å−3 |
127 parameters | Δρmin = −0.32 e Å−3 |
1 restraint | Absolute structure: Flack (1983), with 0 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: −0.01 (7) |
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 | 0.2699 (2) | 0.4471 (3) | 0.32537 (10) | 0.0601 (6) | |
O | 1.0390 (6) | 0.5359 (8) | 0.6520 (2) | 0.0608 (13) | |
N | 0.3998 (7) | 0.7076 (8) | 0.2413 (3) | 0.0521 (14) | |
N3 | 0.5647 (6) | 0.6284 (7) | 0.3491 (2) | 0.0398 (11) | |
H1 | 0.4775 | 0.7884 | 0.2307 | 0.063* | |
H2 | 0.3056 | 0.6890 | 0.2128 | 0.063* | |
C2 | 0.4257 (7) | 0.6096 (8) | 0.3027 (3) | 0.0391 (12) | |
C4 | 0.5454 (8) | 0.5150 (8) | 0.4088 (3) | 0.0395 (12) | |
C5 | 0.4009 (9) | 0.4070 (9) | 0.4040 (4) | 0.0558 (18) | |
H5 | 0.3743 | 0.3213 | 0.4386 | 0.067* | |
C6 | 0.6811 (8) | 0.5214 (9) | 0.4704 (3) | 0.0390 (12) | |
C7 | 0.6429 (8) | 0.4393 (11) | 0.5375 (3) | 0.0501 (14) | |
H7 | 0.5332 | 0.3765 | 0.5425 | 0.060* | |
C8 | 0.7639 (9) | 0.4491 (13) | 0.5969 (3) | 0.0520 (15) | |
H8 | 0.7329 | 0.3968 | 0.6418 | 0.062* | |
C9 | 0.9322 (9) | 0.5368 (10) | 0.5901 (3) | 0.0493 (15) | |
C10 | 0.9713 (8) | 0.6198 (10) | 0.5243 (3) | 0.0483 (14) | |
H10 | 1.0814 | 0.6820 | 0.5194 | 0.058* | |
C11 | 0.8471 (8) | 0.6111 (10) | 0.4651 (3) | 0.0447 (13) | |
H11 | 0.8764 | 0.6670 | 0.4209 | 0.054* | |
C12 | 1.2075 (11) | 0.6320 (16) | 0.6515 (4) | 0.076 (3) | |
H12A | 1.2696 | 0.6185 | 0.6984 | 0.114* | |
H12B | 1.1802 | 0.7517 | 0.6434 | 0.114* | |
H12C | 1.2867 | 0.5906 | 0.6124 | 0.114* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0532 (9) | 0.0602 (9) | 0.0669 (10) | −0.0194 (10) | −0.0176 (7) | 0.0104 (10) |
O | 0.060 (3) | 0.069 (3) | 0.053 (2) | −0.010 (3) | −0.017 (2) | 0.015 (3) |
N | 0.048 (3) | 0.069 (4) | 0.039 (3) | −0.011 (3) | −0.011 (2) | 0.009 (3) |
N3 | 0.036 (2) | 0.049 (3) | 0.035 (2) | 0.000 (2) | 0.0029 (17) | 0.001 (2) |
C2 | 0.041 (3) | 0.044 (3) | 0.032 (2) | −0.002 (3) | 0.004 (2) | −0.008 (2) |
C4 | 0.039 (3) | 0.038 (3) | 0.042 (3) | 0.003 (2) | 0.006 (2) | −0.002 (2) |
C5 | 0.052 (4) | 0.050 (4) | 0.065 (4) | −0.016 (3) | −0.013 (3) | 0.011 (3) |
C6 | 0.041 (3) | 0.040 (3) | 0.036 (3) | 0.003 (2) | 0.005 (2) | 0.000 (2) |
C7 | 0.050 (3) | 0.046 (3) | 0.054 (3) | −0.002 (4) | 0.008 (2) | 0.006 (3) |
C8 | 0.062 (3) | 0.052 (3) | 0.041 (3) | −0.014 (4) | −0.003 (2) | 0.016 (4) |
C9 | 0.055 (4) | 0.047 (3) | 0.046 (3) | 0.010 (3) | −0.002 (3) | 0.000 (3) |
C10 | 0.041 (3) | 0.055 (4) | 0.049 (3) | −0.008 (3) | 0.004 (2) | 0.004 (3) |
C11 | 0.047 (3) | 0.053 (3) | 0.034 (3) | −0.005 (3) | −0.001 (2) | 0.004 (3) |
C12 | 0.068 (5) | 0.096 (7) | 0.064 (4) | −0.019 (5) | −0.019 (4) | 0.001 (5) |
S1—C5 | 1.728 (7) | C7—C8 | 1.379 (8) |
S1—C2 | 1.733 (6) | C7—C6 | 1.393 (8) |
O—C9 | 1.353 (7) | C7—H7 | 0.9300 |
O—C12 | 1.421 (10) | C8—H8 | 0.9300 |
N—C2 | 1.353 (8) | C9—C10 | 1.376 (8) |
N—H1 | 0.8600 | C9—C8 | 1.392 (10) |
N—H2 | 0.8600 | C10—C11 | 1.390 (8) |
N3—C2 | 1.310 (7) | C10—H10 | 0.9300 |
N3—C4 | 1.395 (7) | C11—H11 | 0.9300 |
C4—C5 | 1.336 (8) | C12—H12A | 0.9600 |
C5—H5 | 0.9300 | C12—H12B | 0.9600 |
C6—C11 | 1.383 (9) | C12—H12C | 0.9600 |
C6—C4 | 1.477 (8) | ||
C5—S1—C2 | 88.4 (3) | C6—C7—H7 | 119.2 |
C9—O—C12 | 118.4 (6) | C7—C8—C9 | 120.3 (6) |
C2—N—H1 | 120.0 | C7—C8—H8 | 119.8 |
C2—N—H2 | 120.0 | C9—C8—H8 | 119.8 |
H1—N—H2 | 120.0 | O—C9—C10 | 126.5 (6) |
C2—N3—C4 | 110.2 (5) | O—C9—C8 | 114.6 (6) |
N3—C2—N | 124.3 (6) | C10—C9—C8 | 118.8 (6) |
N3—C2—S1 | 115.0 (4) | C9—C10—C11 | 120.3 (6) |
N—C2—S1 | 120.7 (4) | C9—C10—H10 | 119.8 |
C5—C4—N3 | 114.9 (5) | C11—C10—H10 | 119.8 |
C5—C4—C6 | 125.6 (6) | C6—C11—C10 | 121.6 (5) |
N3—C4—C6 | 119.4 (5) | C6—C11—H11 | 119.2 |
C4—C5—S1 | 111.3 (5) | C10—C11—H11 | 119.2 |
C4—C5—H5 | 124.3 | O—C12—H12A | 109.5 |
S1—C5—H5 | 124.3 | O—C12—H12B | 109.5 |
C11—C6—C7 | 117.3 (5) | H12A—C12—H12B | 109.5 |
C11—C6—C4 | 122.3 (5) | O—C12—H12C | 109.5 |
C7—C6—C4 | 120.4 (5) | H12A—C12—H12C | 109.5 |
C8—C7—C6 | 121.5 (6) | H12B—C12—H12C | 109.5 |
C8—C7—H7 | 119.2 | ||
C2—S1—C5—C4 | 1.0 (5) | C7—C6—C11—C10 | −0.1 (10) |
C5—S1—C2—N3 | 1.3 (5) | C7—C6—C4—N3 | 165.3 (6) |
C5—S1—C2—N | −178.2 (6) | C11—C6—C4—C5 | 166.7 (6) |
C12—O—C9—C10 | 1.5 (12) | C11—C6—C4—N3 | −13.0 (9) |
C12—O—C9—C8 | −175.9 (8) | C8—C7—C6—C11 | 1.0 (10) |
C2—N3—C4—C5 | 3.9 (7) | C8—C7—C6—C4 | −177.4 (8) |
C2—N3—C4—C6 | −176.3 (5) | O—C9—C10—C11 | −179.3 (7) |
C4—N3—C2—N | 176.4 (6) | C6—C7—C8—C9 | −2.4 (12) |
C4—N3—C2—S1 | −3.1 (6) | O—C9—C8—C7 | −179.5 (8) |
N3—C4—C5—S1 | −3.0 (7) | C8—C9—C10—C11 | −2.0 (11) |
C6—C4—C5—S1 | 177.3 (5) | C10—C9—C8—C7 | 2.9 (12) |
C4—C6—C11—C10 | 178.3 (7) | C9—C10—C11—C6 | 0.6 (11) |
C7—C6—C4—C5 | −15.0 (9) |