Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807059715/lh2565sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807059715/lh2565Isup2.hkl |
CCDC reference: 646689
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.006 Å
- R factor = 0.048
- wR factor = 0.123
- Data-to-parameter ratio = 12.2
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT322_ALERT_2_C Check Hybridisation of S1 in Main Residue . ? PLAT322_ALERT_2_C Check Hybridisation of S2 in Main Residue . ? PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 6 PLAT480_ALERT_4_C Long H...A H-Bond Reported H1 .. S1 .. 2.98 Ang.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 4 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 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 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
For related literature, see: Baker & Jones (2005); Ma, Li et al. (2004); Ma, Zhang et al. (2004); Meyers (1974); Mondal et al. (2001); Raper (1985); Streubel (2002); Tarafder et al. (2002); Yang et al. (2000).
For related literature, see: Cheng et al. (2006); Etter (1990).
The reaction was carried out under nitrogen atmosphere with use of standard Schlenk technique. The 2,5-dithiobiurea (0.150 g, 1 mmol) was added to the solution of ethanol (20 ml) with sodium ethoxide (0.136 g, 2 mmol) and stirred for 10 min, and then added salicyladehyde (0.112 g,1 mmol) to the mixture, the mixture was stirred at 353 K and then filtered. an pale yellow solution was obtained, which was filtered. The filtrate was left undisturbed at room temperature for one week. Crystals of the title compound suitable for X-ray analysis were grown from an ethanol solution. yield 65%. NMR(CHCl3):(H) 11.23 (H1, s), 7.02 (H8, s), 7.09 (H6, s), 7.26 (H2, s), 7.56 (H1, s), 7.69 (H1, s), 8.38 (H1, s); (C) 118.1 (C6), 120.8 (C4), 121.8 (C8), 132.6 (C9), 132.9 (C7), 160.5 (C3), 161.4 (C5), 162.0 (C2), 164.2 (C1).
All H atoms were placed in geometrically idealized positions (N—H, O—H and C—H of 0.86, 0.82 and 0.93 Å, respectively) and treated as riding on their parent atoms, with Uiso(H), 1.2Ueq(C,N) and 1.2Ueq(O)
Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL (Sheldrick, 1997b).
C9H8N4OS | F(000) = 912 |
Mr = 220.25 | Dx = 1.521 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 1496 reflections |
a = 5.841 (2) Å | θ = 2.3–21.6° |
b = 30.421 (10) Å | µ = 0.31 mm−1 |
c = 10.915 (4) Å | T = 298 K |
β = 97.282 (4)° | Block, orange |
V = 1923.7 (11) Å3 | 0.22 × 0.15 × 0.11 mm |
Z = 8 |
Bruker SMART CCD diffractometer | 3314 independent reflections |
Radiation source: fine-focus sealed tube | 1830 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.061 |
ϕ and ω scans | θmax = 25.0°, θmin = 1.3° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −6→4 |
Tmin = 0.932, Tmax = 0.958 | k = −36→33 |
9736 measured reflections | l = −12→12 |
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)] = 0.048 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.123 | H-atom parameters constrained |
S = 1.00 | w = 1/[σ2(Fo2) + (0.050P)2] where P = (Fo2 + 2Fc2)/3 |
3314 reflections | (Δ/σ)max < 0.001 |
271 parameters | Δρmax = 0.23 e Å−3 |
0 restraints | Δρmin = −0.27 e Å−3 |
C9H8N4OS | V = 1923.7 (11) Å3 |
Mr = 220.25 | Z = 8 |
Monoclinic, P21/n | Mo Kα radiation |
a = 5.841 (2) Å | µ = 0.31 mm−1 |
b = 30.421 (10) Å | T = 298 K |
c = 10.915 (4) Å | 0.22 × 0.15 × 0.11 mm |
β = 97.282 (4)° |
Bruker SMART CCD diffractometer | 3314 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 1830 reflections with I > 2σ(I) |
Tmin = 0.932, Tmax = 0.958 | Rint = 0.061 |
9736 measured reflections |
R[F2 > 2σ(F2)] = 0.048 | 0 restraints |
wR(F2) = 0.123 | H-atom parameters constrained |
S = 1.00 | Δρmax = 0.23 e Å−3 |
3314 reflections | Δρmin = −0.27 e Å−3 |
271 parameters |
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 | ||
N1 | 0.0020 (5) | 0.02475 (9) | 1.1793 (3) | 0.0413 (8) | |
N2 | 0.1711 (5) | 0.00077 (9) | 1.2504 (3) | 0.0411 (8) | |
N3 | −0.0552 (5) | 0.07223 (9) | 1.0065 (3) | 0.0389 (7) | |
N4 | 0.5670 (5) | −0.01561 (10) | 1.2623 (3) | 0.0485 (9) | |
H4A | 0.5632 | −0.0329 | 1.3243 | 0.058* | |
H4B | 0.6945 | −0.0114 | 1.2324 | 0.058* | |
N5 | 0.2979 (5) | 0.09155 (10) | 0.4459 (3) | 0.0503 (9) | |
N6 | 0.4661 (5) | 0.06510 (10) | 0.5069 (3) | 0.0452 (8) | |
N7 | 0.2222 (5) | 0.14339 (9) | 0.2877 (3) | 0.0413 (8) | |
N8 | 0.8524 (5) | 0.04549 (10) | 0.5046 (3) | 0.0503 (9) | |
H8A | 0.8483 | 0.0271 | 0.5642 | 0.060* | |
H8B | 0.9777 | 0.0490 | 0.4720 | 0.060* | |
O1 | −0.4115 (5) | 0.12430 (9) | 0.9319 (3) | 0.0615 (8) | |
H1 | −0.3375 | 0.1058 | 0.9750 | 0.092* | |
O2 | −0.1463 (5) | 0.19460 (9) | 0.2563 (3) | 0.0648 (8) | |
H2 | −0.0528 | 0.1776 | 0.2931 | 0.097* | |
S1 | 0.37598 (16) | 0.03882 (3) | 1.08484 (9) | 0.0434 (3) | |
S2 | 0.66006 (17) | 0.10490 (3) | 0.34039 (9) | 0.0464 (3) | |
C1 | 0.0808 (6) | 0.04590 (11) | 1.0896 (3) | 0.0349 (9) | |
C2 | 0.3737 (6) | 0.00484 (11) | 1.2122 (3) | 0.0367 (9) | |
C3 | 0.0284 (6) | 0.08513 (11) | 0.9074 (3) | 0.0392 (9) | |
H3 | 0.1723 | 0.0745 | 0.8936 | 0.047* | |
C4 | −0.0879 (7) | 0.11451 (11) | 0.8191 (3) | 0.0398 (9) | |
C5 | −0.3019 (7) | 0.13374 (12) | 0.8338 (4) | 0.0451 (10) | |
C6 | −0.3961 (7) | 0.16421 (13) | 0.7469 (4) | 0.0569 (11) | |
H6 | −0.5356 | 0.1777 | 0.7564 | 0.068* | |
C7 | −0.2859 (8) | 0.17457 (13) | 0.6474 (4) | 0.0596 (12) | |
H7 | −0.3534 | 0.1947 | 0.5898 | 0.072* | |
C8 | −0.0757 (8) | 0.15570 (14) | 0.6304 (4) | 0.0610 (12) | |
H8 | −0.0019 | 0.1631 | 0.5626 | 0.073* | |
C9 | 0.0205 (7) | 0.12576 (12) | 0.7163 (3) | 0.0499 (10) | |
H9 | 0.1606 | 0.1127 | 0.7058 | 0.060* | |
C10 | 0.3698 (6) | 0.11467 (11) | 0.3573 (3) | 0.0401 (9) | |
C11 | 0.6628 (6) | 0.06866 (11) | 0.4623 (3) | 0.0390 (9) | |
C12 | 0.2767 (7) | 0.15904 (11) | 0.1865 (3) | 0.0421 (9) | |
H12 | 0.4159 | 0.1506 | 0.1607 | 0.051* | |
C13 | 0.1291 (7) | 0.18946 (11) | 0.1108 (3) | 0.0412 (9) | |
C14 | −0.0756 (7) | 0.20601 (11) | 0.1478 (4) | 0.0433 (10) | |
C15 | −0.2124 (7) | 0.23435 (12) | 0.0721 (4) | 0.0577 (12) | |
H15 | −0.3474 | 0.2454 | 0.0972 | 0.069* | |
C16 | −0.1507 (9) | 0.24629 (13) | −0.0395 (4) | 0.0629 (13) | |
H16 | −0.2458 | 0.2650 | −0.0907 | 0.075* | |
C17 | 0.0516 (9) | 0.23096 (14) | −0.0776 (4) | 0.0648 (13) | |
H17 | 0.0936 | 0.2396 | −0.1534 | 0.078* | |
C18 | 0.1897 (8) | 0.20292 (13) | −0.0031 (3) | 0.0530 (11) | |
H18 | 0.3260 | 0.1927 | −0.0288 | 0.064* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0324 (18) | 0.0468 (18) | 0.0457 (19) | 0.0019 (16) | 0.0083 (16) | 0.0064 (15) |
N2 | 0.0336 (19) | 0.0492 (19) | 0.0400 (18) | 0.0019 (16) | 0.0033 (15) | 0.0111 (15) |
N3 | 0.0323 (17) | 0.0412 (18) | 0.0431 (19) | 0.0031 (15) | 0.0049 (15) | 0.0009 (15) |
N4 | 0.0322 (18) | 0.062 (2) | 0.054 (2) | 0.0110 (17) | 0.0119 (16) | 0.0189 (16) |
N5 | 0.038 (2) | 0.060 (2) | 0.054 (2) | 0.0055 (18) | 0.0101 (17) | 0.0130 (18) |
N6 | 0.0361 (19) | 0.051 (2) | 0.049 (2) | 0.0029 (17) | 0.0071 (16) | 0.0164 (16) |
N7 | 0.0401 (19) | 0.0381 (18) | 0.0455 (19) | 0.0030 (16) | 0.0041 (16) | 0.0062 (15) |
N8 | 0.0321 (18) | 0.063 (2) | 0.057 (2) | 0.0056 (17) | 0.0094 (16) | 0.0253 (17) |
O1 | 0.0464 (18) | 0.0703 (19) | 0.071 (2) | 0.0158 (15) | 0.0218 (16) | 0.0209 (16) |
O2 | 0.057 (2) | 0.0624 (18) | 0.080 (2) | 0.0175 (15) | 0.0267 (17) | 0.0217 (16) |
S1 | 0.0338 (6) | 0.0514 (6) | 0.0460 (6) | 0.0026 (5) | 0.0087 (5) | 0.0126 (5) |
S2 | 0.0355 (6) | 0.0537 (6) | 0.0505 (6) | 0.0024 (5) | 0.0084 (5) | 0.0150 (5) |
C1 | 0.029 (2) | 0.034 (2) | 0.041 (2) | 0.0009 (17) | 0.0047 (17) | −0.0043 (17) |
C2 | 0.029 (2) | 0.041 (2) | 0.040 (2) | 0.0006 (18) | 0.0028 (18) | 0.0004 (17) |
C3 | 0.037 (2) | 0.038 (2) | 0.044 (2) | −0.0020 (18) | 0.0071 (19) | −0.0019 (18) |
C4 | 0.037 (2) | 0.040 (2) | 0.041 (2) | −0.0031 (19) | 0.0001 (18) | 0.0064 (18) |
C5 | 0.039 (2) | 0.045 (2) | 0.050 (3) | −0.001 (2) | −0.002 (2) | 0.005 (2) |
C6 | 0.047 (3) | 0.051 (3) | 0.068 (3) | 0.009 (2) | −0.007 (2) | 0.010 (2) |
C7 | 0.071 (3) | 0.052 (3) | 0.052 (3) | 0.006 (2) | −0.007 (2) | 0.012 (2) |
C8 | 0.069 (3) | 0.066 (3) | 0.048 (3) | −0.006 (3) | 0.006 (2) | 0.006 (2) |
C9 | 0.051 (3) | 0.051 (2) | 0.047 (2) | 0.001 (2) | 0.005 (2) | 0.006 (2) |
C10 | 0.039 (2) | 0.038 (2) | 0.043 (2) | −0.0005 (19) | 0.0028 (19) | 0.0018 (18) |
C11 | 0.035 (2) | 0.041 (2) | 0.040 (2) | −0.0040 (19) | 0.0025 (18) | 0.0059 (17) |
C12 | 0.034 (2) | 0.041 (2) | 0.051 (3) | 0.0052 (19) | 0.0030 (19) | −0.0048 (19) |
C13 | 0.042 (2) | 0.034 (2) | 0.046 (2) | −0.0014 (19) | 0.0005 (19) | −0.0001 (18) |
C14 | 0.040 (2) | 0.030 (2) | 0.060 (3) | −0.0021 (19) | 0.004 (2) | 0.0052 (19) |
C15 | 0.046 (3) | 0.044 (2) | 0.080 (3) | 0.006 (2) | −0.005 (2) | 0.006 (2) |
C16 | 0.070 (3) | 0.041 (3) | 0.069 (3) | 0.000 (2) | −0.023 (3) | 0.005 (2) |
C17 | 0.091 (4) | 0.054 (3) | 0.047 (3) | −0.010 (3) | −0.005 (3) | 0.005 (2) |
C18 | 0.058 (3) | 0.057 (3) | 0.044 (3) | −0.002 (2) | 0.005 (2) | 0.002 (2) |
N1—C1 | 1.303 (4) | C3—C4 | 1.423 (5) |
N1—N2 | 1.384 (4) | C3—H3 | 0.9300 |
N2—C2 | 1.310 (4) | C4—C9 | 1.399 (5) |
N3—C3 | 1.302 (4) | C4—C5 | 1.407 (5) |
N3—C1 | 1.383 (4) | C5—C6 | 1.389 (5) |
N4—C2 | 1.343 (4) | C6—C7 | 1.367 (5) |
N4—H4A | 0.8600 | C6—H6 | 0.9300 |
N4—H4B | 0.8600 | C7—C8 | 1.389 (6) |
N5—C10 | 1.307 (4) | C7—H7 | 0.9300 |
N5—N6 | 1.375 (4) | C8—C9 | 1.375 (5) |
N6—C11 | 1.308 (4) | C8—H8 | 0.9300 |
N7—C12 | 1.279 (4) | C9—H9 | 0.9300 |
N7—C10 | 1.385 (4) | C12—C13 | 1.450 (5) |
N8—C11 | 1.344 (4) | C12—H12 | 0.9300 |
N8—H8A | 0.8600 | C13—C18 | 1.397 (5) |
N8—H8B | 0.8600 | C13—C14 | 1.403 (5) |
O1—C5 | 1.346 (4) | C14—C15 | 1.377 (5) |
O1—H1 | 0.8200 | C15—C16 | 1.363 (5) |
O2—C14 | 1.349 (4) | C15—H15 | 0.9300 |
O2—H2 | 0.8200 | C16—C17 | 1.382 (6) |
S1—C2 | 1.733 (4) | C16—H16 | 0.9300 |
S1—C1 | 1.745 (4) | C17—C18 | 1.368 (6) |
S2—C11 | 1.726 (4) | C17—H17 | 0.9300 |
S2—C10 | 1.754 (4) | C18—H18 | 0.9300 |
C1—N1—N2 | 112.8 (3) | C6—C7—H7 | 119.2 |
C2—N2—N1 | 112.3 (3) | C8—C7—H7 | 119.2 |
C3—N3—C1 | 118.3 (3) | C9—C8—C7 | 118.3 (4) |
C2—N4—H4A | 120.0 | C9—C8—H8 | 120.9 |
C2—N4—H4B | 120.0 | C7—C8—H8 | 120.9 |
H4A—N4—H4B | 120.0 | C8—C9—C4 | 121.4 (4) |
C10—N5—N6 | 113.4 (3) | C8—C9—H9 | 119.3 |
C11—N6—N5 | 112.2 (3) | C4—C9—H9 | 119.3 |
C12—N7—C10 | 120.2 (3) | N5—C10—N7 | 120.6 (3) |
C11—N8—H8A | 120.0 | N5—C10—S2 | 113.1 (3) |
C11—N8—H8B | 120.0 | N7—C10—S2 | 126.3 (3) |
H8A—N8—H8B | 120.0 | N6—C11—N8 | 123.6 (3) |
C5—O1—H1 | 109.5 | N6—C11—S2 | 114.7 (3) |
C14—O2—H2 | 109.5 | N8—C11—S2 | 121.8 (3) |
C2—S1—C1 | 86.66 (17) | N7—C12—C13 | 122.3 (3) |
C11—S2—C10 | 86.66 (18) | N7—C12—H12 | 118.8 |
N1—C1—N3 | 123.4 (3) | C13—C12—H12 | 118.8 |
N1—C1—S1 | 113.9 (3) | C18—C13—C14 | 118.2 (4) |
N3—C1—S1 | 122.7 (3) | C18—C13—C12 | 119.7 (4) |
N2—C2—N4 | 125.0 (3) | C14—C13—C12 | 122.1 (3) |
N2—C2—S1 | 114.3 (3) | O2—C14—C15 | 118.0 (4) |
N4—C2—S1 | 120.7 (3) | O2—C14—C13 | 121.8 (3) |
N3—C3—C4 | 123.7 (3) | C15—C14—C13 | 120.2 (4) |
N3—C3—H3 | 118.1 | C16—C15—C14 | 120.3 (4) |
C4—C3—H3 | 118.1 | C16—C15—H15 | 119.9 |
C9—C4—C5 | 119.3 (3) | C14—C15—H15 | 119.9 |
C9—C4—C3 | 118.1 (4) | C15—C16—C17 | 120.8 (4) |
C5—C4—C3 | 122.6 (3) | C15—C16—H16 | 119.6 |
O1—C5—C6 | 119.9 (4) | C17—C16—H16 | 119.6 |
O1—C5—C4 | 121.4 (3) | C18—C17—C16 | 119.6 (4) |
C6—C5—C4 | 118.7 (4) | C18—C17—H17 | 120.2 |
C7—C6—C5 | 120.7 (4) | C16—C17—H17 | 120.2 |
C7—C6—H6 | 119.6 | C17—C18—C13 | 121.0 (4) |
C5—C6—H6 | 119.6 | C17—C18—H18 | 119.5 |
C6—C7—C8 | 121.6 (4) | C13—C18—H18 | 119.5 |
C1—N1—N2—C2 | 0.3 (4) | C3—C4—C9—C8 | −176.6 (3) |
C10—N5—N6—C11 | −0.4 (5) | N6—N5—C10—N7 | −179.3 (3) |
N2—N1—C1—N3 | −179.7 (3) | N6—N5—C10—S2 | 0.7 (4) |
N2—N1—C1—S1 | −0.7 (4) | C12—N7—C10—N5 | −165.7 (3) |
C3—N3—C1—N1 | −167.2 (3) | C12—N7—C10—S2 | 14.3 (5) |
C3—N3—C1—S1 | 13.9 (4) | C11—S2—C10—N5 | −0.6 (3) |
C2—S1—C1—N1 | 0.7 (3) | C11—S2—C10—N7 | 179.3 (3) |
C2—S1—C1—N3 | 179.7 (3) | N5—N6—C11—N8 | −178.6 (3) |
N1—N2—C2—N4 | −178.4 (3) | N5—N6—C11—S2 | −0.1 (4) |
N1—N2—C2—S1 | 0.2 (4) | C10—S2—C11—N6 | 0.4 (3) |
C1—S1—C2—N2 | −0.5 (3) | C10—S2—C11—N8 | 178.9 (3) |
C1—S1—C2—N4 | 178.1 (3) | C10—N7—C12—C13 | −179.5 (3) |
C1—N3—C3—C4 | −175.8 (3) | N7—C12—C13—C18 | −175.3 (3) |
N3—C3—C4—C9 | −179.9 (3) | N7—C12—C13—C14 | 4.4 (5) |
N3—C3—C4—C5 | 2.6 (5) | C18—C13—C14—O2 | 179.9 (3) |
C9—C4—C5—O1 | −179.2 (3) | C12—C13—C14—O2 | 0.2 (5) |
C3—C4—C5—O1 | −1.7 (6) | C18—C13—C14—C15 | 0.7 (5) |
C9—C4—C5—C6 | −1.6 (5) | C12—C13—C14—C15 | −179.0 (3) |
C3—C4—C5—C6 | 176.0 (3) | O2—C14—C15—C16 | −178.8 (3) |
O1—C5—C6—C7 | 179.3 (4) | C13—C14—C15—C16 | 0.4 (6) |
C4—C5—C6—C7 | 1.5 (6) | C14—C15—C16—C17 | −1.3 (6) |
C5—C6—C7—C8 | −1.0 (7) | C15—C16—C17—C18 | 1.0 (6) |
C6—C7—C8—C9 | 0.4 (6) | C16—C17—C18—C13 | 0.1 (6) |
C7—C8—C9—C4 | −0.4 (6) | C14—C13—C18—C17 | −1.0 (6) |
C5—C4—C9—C8 | 1.0 (6) | C12—C13—C18—C17 | 178.8 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···S1i | 0.82 | 2.98 | 3.408 (3) | 115 |
O2—H2···N7 | 0.82 | 1.92 | 2.644 (4) | 147 |
O1—H1···N3 | 0.82 | 1.93 | 2.660 (4) | 147 |
N8—H8B···N5ii | 0.86 | 2.32 | 3.093 (4) | 150 |
N8—H8A···N2iii | 0.86 | 2.21 | 3.041 (4) | 162 |
N4—H4B···N1ii | 0.86 | 2.24 | 3.061 (4) | 159 |
N4—H4A···N6iii | 0.86 | 2.11 | 2.962 (4) | 170 |
Symmetry codes: (i) x−1, y, z; (ii) x+1, y, z; (iii) −x+1, −y, −z+2. |
Experimental details
Crystal data | |
Chemical formula | C9H8N4OS |
Mr | 220.25 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 298 |
a, b, c (Å) | 5.841 (2), 30.421 (10), 10.915 (4) |
β (°) | 97.282 (4) |
V (Å3) | 1923.7 (11) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.31 |
Crystal size (mm) | 0.22 × 0.15 × 0.11 |
Data collection | |
Diffractometer | Bruker SMART CCD diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.932, 0.958 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 9736, 3314, 1830 |
Rint | 0.061 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.048, 0.123, 1.00 |
No. of reflections | 3314 |
No. of parameters | 271 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.23, −0.27 |
Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 1997a), SHELXL97 (Sheldrick, 1997a), SHELXTL (Sheldrick, 1997b).
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···S1i | 0.82 | 2.98 | 3.408 (3) | 114.6 |
O2—H2···N7 | 0.82 | 1.92 | 2.644 (4) | 146.6 |
O1—H1···N3 | 0.82 | 1.93 | 2.660 (4) | 147.1 |
N8—H8B···N5ii | 0.86 | 2.32 | 3.093 (4) | 149.5 |
N8—H8A···N2iii | 0.86 | 2.21 | 3.041 (4) | 162.0 |
N4—H4B···N1ii | 0.86 | 2.24 | 3.061 (4) | 158.6 |
N4—H4A···N6iii | 0.86 | 2.11 | 2.962 (4) | 169.5 |
Symmetry codes: (i) x−1, y, z; (ii) x+1, y, z; (iii) −x+1, −y, −z+2. |
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Schiff bases have been intensively investigated recently owing to their diverse biological activities, such as antibacterial, antitumor activities etc. (Yang et al., 2000; Mondal et al., 2001; Tarafder et al., 2002). On the other hand, heterocycles in organic synthesis is a current research (Meyers, 1974) and lots of organic heterocyclic compounds have been synthesized (Raper, 1985; Streubel, 2002; Baker & Jones, 2005) to study their various characteristics.
We are interested in 2,5-dithiobiurea and salicylaldehyde and report here the structure of the title compound. The asymmetric unit of the title compound contains two crystallographically independent molecules, with almost identical bond lengths and angles. The asymmetric unit and atom numbering scheme are shown in (Fig. 1).
The title compound comprises a 2-amino-1,3,4- thiadiazole moiety and 2-hydroxyphenyl group linked by a C=N bond which has a Z geometry. In this Z isomer, the C3—C4 bond is trans with respect to the N3—C1 bond. The geometries of the two molecules in the asymmetric unit are essentially the same, so only one independent molecule is discussed in detail here.
The bond angles around atoms N3 and C3 deviate from 120 ° and this is in general agreement with observation for a similar type of compound (Cheng et al., 2006). The angles C3=N3—C1, C4—C3=N3 and H3—C3—C4 [118.33, 123.71 and 118.18 °, respectively] are distorted as a consequence of the strain induced by the double-bond linkage at C3=N3.
For the five-membered 1,3,4-thiadiazole ring, the N1—N2 bond length (1.384 (4) Å) and the C=N bond lengths (C1=N1 1.303 (4) Å and C2=N2 1.310 (4) Å, respectively) are consistent with those reported in the literature (Ma, Zhang et al., 2004); the C—S bond lengths (C1—S1 1.745 (4) Å and C2—S1 1.733 (4) Å, respectively) are consistent with literature reported (Ma, Li et al., 2004).
The molecular structure and crystal packing of are stabilized by intermolecular N—H···N and O—H···S hydrogen bonds. N—H···N hydrogen bonds generate centrosymmetric R228 (Etter, 1990) rings (Fig.2), forming dimers which are linked through the N—H···N hydrogen bonds to form a second type of ring motif, of R4410 type. The combination of these rings produces a linear chains, which run along [100] and are stabilized by weak intermolecular O—H···S hydrogen bonds.