Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806052238/kj2029sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806052238/kj2029Isup2.hkl |
CCDC reference: 636720
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.002 Å
- R factor = 0.040
- wR factor = 0.106
- Data-to-parameter ratio = 26.3
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT021_ALERT_1_B Ratio Unique / Expected Reflections too High ... 1.13
Alert level C PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size ....... 0.79 mm PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ?
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 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 1 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
Data collection: APEX2 (Bruker, 2006); cell refinement: APEX2; data reduction: APEX2; program(s) used to solve structure: SHELXTL (Bruker, 2000); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.
C8H6N2OS | F(000) = 368 |
Mr = 178.21 | Dx = 1.440 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 11.3414 (15) Å | Cell parameters from 3166 reflections |
b = 4.6589 (16) Å | θ = 3.7–30.6° |
c = 16.0242 (7) Å | µ = 0.34 mm−1 |
β = 103.845 (5)° | T = 298 K |
V = 822.1 (3) Å3 | Plate, colourless |
Z = 4 | 0.79 × 0.23 × 0.07 mm |
Bruker APEXII CCD area-detector diffractometer | 2888 independent reflections |
Radiation source: fine-focus sealed tube | 2386 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.034 |
φ and ω scans | θmax = 30.7°, θmin = 2.0° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −15→15 |
Tmin = 0.775, Tmax = 0.977 | k = −6→6 |
12966 measured reflections | l = −22→22 |
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)] = 0.040 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.106 | H-atom parameters constrained |
S = 1.01 | w = 1/[σ2(Fo2) + (0.0696P)2] where P = (Fo2 + 2Fc2)/3 |
2888 reflections | (Δ/σ)max = 0.001 |
110 parameters | Δρmax = 0.27 e Å−3 |
0 restraints | Δρmin = −0.21 e Å−3 |
Experimental. IR (Medium?, ν, cm-1): 3108 (–NH), 1610 (C═N), 1145 (–C═S); 1H NMR (DMSO-d6, TMS, δ, p.p.m.): 13.56 (s, 1H, NH), 8.55–7.25 (m, 5H, phenyl); 13C NMR (DMSO-d6, TMS, δ, p.p.m.): 131.48 (C1), 128.68 (C2, C6),125.29 (C3, C5), 121.73 (C4), 159.72 (C7), 176.74 (C8). The IR and NMR data confirm the presence of the thione tautomer in the solid state as well as in solution. |
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 | 0.68387 (3) | 1.03196 (9) | 0.45854 (2) | 0.04557 (13) | |
O1 | 0.60441 (7) | 0.6440 (2) | 0.33504 (6) | 0.0379 (2) | |
C1 | 0.49558 (11) | 0.2792 (3) | 0.23604 (8) | 0.0372 (3) | |
C7 | 0.50227 (11) | 0.4791 (3) | 0.30667 (9) | 0.0374 (3) | |
C8 | 0.58430 (11) | 0.8025 (3) | 0.40210 (8) | 0.0375 (3) | |
N1 | 0.42105 (12) | 0.5232 (3) | 0.34905 (9) | 0.0477 (3) | |
C6 | 0.59515 (12) | 0.2282 (4) | 0.20132 (10) | 0.0454 (3) | |
H6A | 0.6678 | 0.3252 | 0.2226 | 0.055* | |
N2 | 0.47371 (10) | 0.7277 (3) | 0.40827 (8) | 0.0475 (3) | |
H2B | 0.4386 | 0.7996 | 0.4455 | 0.057* | |
C5 | 0.58552 (15) | 0.0333 (4) | 0.13530 (10) | 0.0531 (4) | |
H5A | 0.6521 | −0.0037 | 0.1126 | 0.064* | |
C2 | 0.38610 (12) | 0.1370 (4) | 0.20291 (10) | 0.0470 (3) | |
H2A | 0.3193 | 0.1714 | 0.2257 | 0.056* | |
C4 | 0.47638 (15) | −0.1079 (4) | 0.10273 (10) | 0.0544 (4) | |
H4A | 0.4702 | −0.2389 | 0.0581 | 0.065* | |
C3 | 0.37748 (16) | −0.0554 (4) | 0.13593 (11) | 0.0536 (4) | |
H3A | 0.3045 | −0.1496 | 0.1133 | 0.064* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.04042 (19) | 0.0496 (2) | 0.0479 (2) | −0.00313 (15) | 0.01284 (15) | −0.00394 (16) |
O1 | 0.0333 (4) | 0.0403 (5) | 0.0424 (5) | 0.0001 (4) | 0.0134 (4) | −0.0003 (4) |
C1 | 0.0347 (6) | 0.0375 (7) | 0.0395 (6) | 0.0024 (5) | 0.0092 (5) | 0.0031 (5) |
C7 | 0.0303 (5) | 0.0392 (7) | 0.0431 (6) | 0.0015 (5) | 0.0093 (5) | 0.0041 (6) |
C8 | 0.0378 (6) | 0.0369 (7) | 0.0396 (6) | 0.0051 (5) | 0.0125 (5) | 0.0047 (5) |
N1 | 0.0366 (6) | 0.0552 (8) | 0.0547 (7) | −0.0038 (5) | 0.0174 (5) | −0.0099 (6) |
C6 | 0.0361 (6) | 0.0533 (9) | 0.0487 (7) | −0.0028 (6) | 0.0136 (6) | −0.0039 (6) |
N2 | 0.0400 (6) | 0.0553 (8) | 0.0522 (7) | −0.0027 (6) | 0.0211 (5) | −0.0110 (6) |
C5 | 0.0478 (8) | 0.0624 (11) | 0.0543 (9) | 0.0004 (7) | 0.0227 (7) | −0.0050 (8) |
C2 | 0.0351 (6) | 0.0533 (9) | 0.0538 (8) | −0.0028 (6) | 0.0130 (6) | −0.0025 (7) |
C4 | 0.0616 (10) | 0.0552 (10) | 0.0466 (8) | −0.0018 (8) | 0.0131 (7) | −0.0085 (7) |
C3 | 0.0478 (8) | 0.0555 (10) | 0.0546 (9) | −0.0086 (7) | 0.0069 (7) | −0.0066 (7) |
S1—C8 | 1.6574 (15) | C6—H6A | 0.9300 |
O1—C8 | 1.3672 (16) | N2—H2B | 0.8600 |
O1—C7 | 1.3739 (16) | C5—C4 | 1.389 (2) |
C1—C6 | 1.3936 (19) | C5—H5A | 0.9300 |
C1—C2 | 1.3953 (19) | C2—C3 | 1.384 (2) |
C1—C7 | 1.454 (2) | C2—H2A | 0.9300 |
C7—N1 | 1.2850 (19) | C4—C3 | 1.373 (2) |
C8—N2 | 1.3281 (17) | C4—H4A | 0.9300 |
N1—N2 | 1.3761 (18) | C3—H3A | 0.9300 |
C6—C5 | 1.378 (2) | ||
C8—O1—C7 | 106.03 (10) | C8—N2—H2B | 123.5 |
C6—C1—C2 | 119.97 (14) | N1—N2—H2B | 123.5 |
C6—C1—C7 | 121.59 (12) | C6—C5—C4 | 120.02 (15) |
C2—C1—C7 | 118.44 (12) | C6—C5—H5A | 120.0 |
N1—C7—O1 | 112.96 (12) | C4—C5—H5A | 120.0 |
N1—C7—C1 | 127.12 (13) | C3—C2—C1 | 119.60 (14) |
O1—C7—C1 | 119.92 (12) | C3—C2—H2A | 120.2 |
N2—C8—O1 | 104.77 (12) | C1—C2—H2A | 120.2 |
N2—C8—S1 | 131.38 (12) | C3—C4—C5 | 120.48 (15) |
O1—C8—S1 | 123.86 (10) | C3—C4—H4A | 119.8 |
C7—N1—N2 | 103.14 (12) | C5—C4—H4A | 119.8 |
C5—C6—C1 | 119.71 (14) | C4—C3—C2 | 120.20 (15) |
C5—C6—H6A | 120.1 | C4—C3—H3A | 119.9 |
C1—C6—H6A | 120.1 | C2—C3—H3A | 119.9 |
C8—N2—N1 | 113.09 (12) | ||
C8—O1—C7—N1 | 0.75 (15) | C7—C1—C6—C5 | 178.92 (14) |
C8—O1—C7—C1 | −178.73 (11) | O1—C8—N2—N1 | 1.02 (17) |
C6—C1—C7—N1 | −172.88 (15) | S1—C8—N2—N1 | −179.02 (12) |
C2—C1—C7—N1 | 7.2 (2) | C7—N1—N2—C8 | −0.58 (18) |
C6—C1—C7—O1 | 6.5 (2) | C1—C6—C5—C4 | 1.0 (3) |
C2—C1—C7—O1 | −173.42 (13) | C6—C1—C2—C3 | 0.4 (2) |
C7—O1—C8—N2 | −1.02 (14) | C7—C1—C2—C3 | −179.69 (14) |
C7—O1—C8—S1 | 179.01 (10) | C6—C5—C4—C3 | −0.1 (3) |
O1—C7—N1—N2 | −0.13 (16) | C5—C4—C3—C2 | −0.6 (3) |
C1—C7—N1—N2 | 179.30 (13) | C1—C2—C3—C4 | 0.5 (3) |
C2—C1—C6—C5 | −1.2 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2B···S1i | 0.86 | 2.44 | 3.2907 (13) | 173 |
Symmetry code: (i) −x+1, −y+2, −z+1. |
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