organic compounds
1-(2-Hydroxybenzoyl)thiosemicarbazide hemihydrate
aCollege of Chemistry and Chemical Technology, Binzhou University, Binzhou 256600, Shandong, People's Republic of China
*Correspondence e-mail: fanchuangang2009@163.com
The 8H9N3O2S·0.5H2O, contains two thiosemicarbazide molecules with the short distance of 3.521 (3) Å between the centroids of the benzene rings, and one water molecule. In the two independent molecules, the benzene rings and the thiosemicarbazone fragments are twisted at 9.2 (3) and 18.5 (3)°. An extensive three-dimensional hydrogen-bonding network, formed by intermolecular N—H⋯O, N—H⋯S and O—H⋯O hydrogen bonds, consolidates the crystal packing.
of the title compound, CRelated literature
For the biological activities of thiosemicarbazide derivatives, see: Desai et al. (1984); Shukla et al. (1984). For related structures, see: Gors et al. (1979); Jin (2007).
Experimental
Crystal data
|
Refinement
|
Data collection: SMART (Bruker, 2007); cell SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.
Supporting information
https://doi.org/10.1107/S1600536810044259/cv2777sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810044259/cv2777Isup2.hkl
Salicylyl hydrazine (10 mmol), potassium thiocyanate (12 mmol) and 10 ml me thanol-water (1:1) were mixed in 50 ml flask. After refluxing 12 h at 373 K, the resulting mixture was recrystalized from solution, affording the title compound as a colorless crystalline solid.
All H atoms were placed in geometrically idealized positions (N—H = 0.86, O—H= 0.82-0.85 and C—H = 0.93 Å) and treated as riding on their parent atoms, with Uiso(H) = 1.2U-1.5 Ueq of the parent atom.
Thiosemicarbazide compounds exhibit various biological activities such as anti-bacterial, anti-fungal and especially anti-tuberculosis (Shukla et al., 1984; Desai et al., 1984). Herewith we present the title compound (I), a new thiosemicarbazide compound.
The
of (I) contains two independent molecules and one crystalline water molecule (Fig. 1). The bond lengths and angles are normal and comparable to the values observed in similar compounds (Gors et al., 1979; Jin, 2007). In two independent molecules, the benzene rings and the thiosemicarbazone fragments (C/N/N) are twisted at 9.2 (3)° and 18.5 (3)°, respectively.In the
the three-dimensional network structure was formed by the intermolecular N—H···O, N—H···S and O—H···O hydrogen bonds (Table 1).For the biological activities of thiosemicarbazide derivatives, see: Desai et al. (1984); Shukla et al. (1984). For the crystal structures of related compounds, see: Gors et al. (1979); Jin (2007).
Data collection: SMART (Bruker, 2007); cell
SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).Fig. 1. The content of asymmetric unit of the title compound showing the atomic numbering scheme and 30% probability displacement ellipsoids. |
C16H20N6O5S2 | F(000) = 916 |
Mr = 440.50 | Dx = 1.474 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 9.0718 (11) Å | Cell parameters from 2367 reflections |
b = 21.608 (2) Å | θ = 2.2–25.7° |
c = 10.1035 (13) Å | µ = 0.31 mm−1 |
β = 90.173 (1)° | T = 298 K |
V = 1980.5 (4) Å3 | Block, yellow |
Z = 4 | 0.45 × 0.20 × 0.17 mm |
Bruker SMART APEX CCD area-detector diffractometer | 3487 independent reflections |
Radiation source: fine-focus sealed tube | 2202 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.041 |
φ and ω scans | θmax = 25.0°, θmin = 1.9° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −10→10 |
Tmin = 0.873, Tmax = 0.949 | k = −21→25 |
9862 measured reflections | l = −11→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)] = 0.047 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.122 | H-atom parameters constrained |
S = 1.01 | w = 1/[σ2(Fo2) + (0.0468P)2 + 1.2463P] where P = (Fo2 + 2Fc2)/3 |
3487 reflections | (Δ/σ)max < 0.001 |
262 parameters | Δρmax = 0.37 e Å−3 |
0 restraints | Δρmin = −0.33 e Å−3 |
C16H20N6O5S2 | V = 1980.5 (4) Å3 |
Mr = 440.50 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 9.0718 (11) Å | µ = 0.31 mm−1 |
b = 21.608 (2) Å | T = 298 K |
c = 10.1035 (13) Å | 0.45 × 0.20 × 0.17 mm |
β = 90.173 (1)° |
Bruker SMART APEX CCD area-detector diffractometer | 3487 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 2202 reflections with I > 2σ(I) |
Tmin = 0.873, Tmax = 0.949 | Rint = 0.041 |
9862 measured reflections |
R[F2 > 2σ(F2)] = 0.047 | 0 restraints |
wR(F2) = 0.122 | H-atom parameters constrained |
S = 1.01 | Δρmax = 0.37 e Å−3 |
3487 reflections | Δρmin = −0.33 e Å−3 |
262 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 | Occ. (<1) | |
N1 | 0.4021 (3) | 0.07227 (12) | 0.5682 (3) | 0.0401 (7) | |
H1 | 0.3330 | 0.0634 | 0.6231 | 0.048* | |
N2 | 0.5273 (3) | 0.10117 (11) | 0.6152 (3) | 0.0392 (7) | |
H2 | 0.6033 | 0.0794 | 0.6354 | 0.047* | |
N3 | 0.4849 (3) | 0.07466 (12) | 0.3544 (3) | 0.0443 (7) | |
H3A | 0.5612 | 0.0950 | 0.3806 | 0.053* | |
H3B | 0.4746 | 0.0655 | 0.2721 | 0.053* | |
N4 | 0.8800 (3) | 0.06010 (11) | 0.3372 (3) | 0.0399 (7) | |
H4' | 0.8275 | 0.0385 | 0.3908 | 0.048* | |
N5 | 0.9398 (3) | 0.11556 (11) | 0.3803 (3) | 0.0362 (7) | |
H5 | 1.0322 | 0.1177 | 0.3992 | 0.043* | |
N6 | 0.9674 (3) | 0.07614 (13) | 0.1292 (3) | 0.0527 (8) | |
H6A | 0.9949 | 0.1125 | 0.1534 | 0.063* | |
H6B | 0.9827 | 0.0639 | 0.0495 | 0.063* | |
O1 | 0.4251 (2) | 0.19444 (10) | 0.5943 (2) | 0.0386 (6) | |
O2 | 0.5712 (3) | 0.29296 (10) | 0.6415 (2) | 0.0441 (6) | |
H2A | 0.5042 | 0.2722 | 0.6100 | 0.066* | |
O3 | 0.7237 (2) | 0.16510 (10) | 0.3629 (2) | 0.0439 (6) | |
O4 | 1.1396 (2) | 0.17295 (9) | 0.5240 (2) | 0.0408 (6) | |
H4 | 1.2180 | 0.1806 | 0.5612 | 0.061* | |
O5 | 0.3935 (7) | 0.0087 (2) | 0.0932 (4) | 0.172 (2) | |
H5D | 0.3575 | −0.0063 | 0.1638 | 0.206* | 0.50 |
H5B | 0.4780 | 0.0030 | 0.0591 | 0.206* | 0.50 |
S1 | 0.23175 (9) | 0.01686 (4) | 0.39559 (9) | 0.0415 (3) | |
S2 | 0.84286 (14) | −0.03260 (5) | 0.17448 (11) | 0.0703 (4) | |
C1 | 0.3839 (4) | 0.05757 (13) | 0.4406 (3) | 0.0336 (8) | |
C2 | 0.5320 (3) | 0.16295 (14) | 0.6297 (3) | 0.0307 (7) | |
C3 | 0.6647 (3) | 0.19040 (13) | 0.6870 (3) | 0.0287 (7) | |
C4 | 0.6763 (3) | 0.25507 (14) | 0.6910 (3) | 0.0315 (7) | |
C5 | 0.7998 (4) | 0.28273 (16) | 0.7474 (3) | 0.0404 (8) | |
H5A | 0.8066 | 0.3256 | 0.7513 | 0.049* | |
C6 | 0.9113 (4) | 0.24687 (18) | 0.7971 (3) | 0.0448 (9) | |
H6 | 0.9938 | 0.2657 | 0.8342 | 0.054* | |
C7 | 0.9031 (4) | 0.18322 (17) | 0.7929 (3) | 0.0445 (9) | |
H7 | 0.9797 | 0.1593 | 0.8267 | 0.053* | |
C8 | 0.7813 (3) | 0.15549 (15) | 0.7387 (3) | 0.0377 (8) | |
H8 | 0.7761 | 0.1125 | 0.7361 | 0.045* | |
C9 | 0.9021 (4) | 0.03945 (15) | 0.2138 (4) | 0.0412 (8) | |
C10 | 0.8546 (3) | 0.16613 (14) | 0.3929 (3) | 0.0307 (7) | |
C11 | 0.9288 (3) | 0.22405 (13) | 0.4381 (3) | 0.0288 (7) | |
C12 | 1.0660 (3) | 0.22665 (13) | 0.5004 (3) | 0.0303 (7) | |
C13 | 1.1241 (4) | 0.28340 (14) | 0.5386 (3) | 0.0370 (8) | |
H13 | 1.2142 | 0.2849 | 0.5826 | 0.044* | |
C14 | 1.0501 (4) | 0.33711 (15) | 0.5122 (3) | 0.0425 (9) | |
H14 | 1.0910 | 0.3749 | 0.5365 | 0.051* | |
C15 | 0.9147 (4) | 0.33536 (15) | 0.4495 (3) | 0.0431 (9) | |
H15 | 0.8642 | 0.3719 | 0.4314 | 0.052* | |
C16 | 0.8552 (4) | 0.27936 (14) | 0.4143 (3) | 0.0373 (8) | |
H16 | 0.7633 | 0.2784 | 0.3733 | 0.045* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0370 (17) | 0.0357 (16) | 0.0475 (18) | −0.0102 (13) | −0.0024 (14) | −0.0063 (14) |
N2 | 0.0284 (16) | 0.0278 (15) | 0.0613 (19) | −0.0024 (12) | −0.0136 (13) | −0.0030 (13) |
N3 | 0.0396 (18) | 0.0449 (17) | 0.0485 (18) | −0.0078 (14) | −0.0004 (15) | −0.0042 (14) |
N4 | 0.0388 (17) | 0.0296 (15) | 0.0514 (18) | −0.0092 (12) | 0.0036 (14) | −0.0057 (13) |
N5 | 0.0256 (15) | 0.0272 (14) | 0.0558 (18) | −0.0054 (12) | −0.0035 (13) | −0.0093 (13) |
N6 | 0.078 (2) | 0.0351 (17) | 0.0453 (18) | −0.0171 (16) | 0.0066 (16) | −0.0064 (15) |
O1 | 0.0281 (13) | 0.0323 (12) | 0.0555 (14) | 0.0039 (10) | −0.0091 (11) | −0.0004 (11) |
O2 | 0.0432 (15) | 0.0294 (12) | 0.0596 (15) | 0.0017 (10) | −0.0031 (12) | −0.0032 (11) |
O3 | 0.0241 (13) | 0.0436 (14) | 0.0639 (16) | −0.0005 (10) | −0.0073 (11) | −0.0033 (12) |
O4 | 0.0315 (13) | 0.0331 (13) | 0.0577 (15) | 0.0027 (10) | −0.0120 (11) | −0.0027 (11) |
O5 | 0.299 (7) | 0.114 (3) | 0.102 (3) | −0.017 (4) | 0.030 (4) | −0.006 (3) |
S1 | 0.0350 (5) | 0.0327 (5) | 0.0567 (6) | −0.0036 (4) | −0.0089 (4) | −0.0056 (4) |
S2 | 0.1012 (9) | 0.0420 (6) | 0.0677 (7) | −0.0309 (6) | 0.0138 (6) | −0.0172 (5) |
C1 | 0.0309 (19) | 0.0198 (16) | 0.050 (2) | 0.0055 (13) | −0.0033 (16) | −0.0016 (15) |
C2 | 0.0303 (18) | 0.0316 (18) | 0.0302 (17) | −0.0006 (15) | 0.0035 (14) | 0.0010 (14) |
C3 | 0.0264 (17) | 0.0303 (17) | 0.0293 (17) | −0.0022 (13) | 0.0012 (13) | −0.0030 (14) |
C4 | 0.0308 (19) | 0.0325 (18) | 0.0313 (18) | 0.0019 (14) | 0.0051 (14) | −0.0033 (15) |
C5 | 0.041 (2) | 0.0376 (19) | 0.043 (2) | −0.0130 (16) | 0.0075 (17) | −0.0115 (16) |
C6 | 0.030 (2) | 0.064 (3) | 0.040 (2) | −0.0169 (18) | 0.0041 (16) | −0.0147 (19) |
C7 | 0.030 (2) | 0.058 (2) | 0.045 (2) | −0.0004 (17) | −0.0064 (16) | −0.0021 (18) |
C8 | 0.036 (2) | 0.0357 (19) | 0.0410 (19) | 0.0022 (15) | −0.0036 (16) | −0.0021 (16) |
C9 | 0.040 (2) | 0.0313 (19) | 0.052 (2) | −0.0035 (15) | −0.0020 (17) | −0.0036 (17) |
C10 | 0.0270 (19) | 0.0315 (18) | 0.0337 (18) | −0.0003 (14) | 0.0046 (14) | 0.0012 (14) |
C11 | 0.0253 (17) | 0.0284 (17) | 0.0328 (17) | −0.0003 (13) | 0.0068 (14) | −0.0011 (14) |
C12 | 0.0288 (18) | 0.0285 (17) | 0.0338 (18) | 0.0000 (14) | 0.0034 (14) | −0.0009 (14) |
C13 | 0.0326 (19) | 0.0354 (19) | 0.043 (2) | −0.0050 (15) | 0.0012 (16) | −0.0043 (16) |
C14 | 0.048 (2) | 0.0285 (19) | 0.051 (2) | −0.0053 (17) | 0.0093 (18) | −0.0096 (16) |
C15 | 0.046 (2) | 0.0274 (18) | 0.056 (2) | 0.0080 (16) | 0.0064 (18) | 0.0025 (16) |
C16 | 0.034 (2) | 0.0360 (19) | 0.042 (2) | 0.0057 (15) | 0.0076 (15) | 0.0017 (16) |
N1—C1 | 1.338 (4) | S1—C1 | 1.697 (3) |
N1—N2 | 1.379 (3) | S2—C9 | 1.694 (3) |
N1—H1 | 0.8600 | C2—C3 | 1.460 (4) |
N2—C2 | 1.344 (4) | C3—C8 | 1.399 (4) |
N2—H2 | 0.8600 | C3—C4 | 1.402 (4) |
N3—C1 | 1.319 (4) | C4—C5 | 1.391 (4) |
N3—H3A | 0.8600 | C5—C6 | 1.369 (5) |
N3—H3B | 0.8600 | C5—H5A | 0.9300 |
N4—C9 | 1.340 (4) | C6—C7 | 1.378 (5) |
N4—N5 | 1.385 (3) | C6—H6 | 0.9300 |
N4—H4' | 0.8600 | C7—C8 | 1.370 (4) |
N5—C10 | 1.345 (4) | C7—H7 | 0.9300 |
N5—H5 | 0.8600 | C8—H8 | 0.9300 |
N6—C9 | 1.308 (4) | C10—C11 | 1.492 (4) |
N6—H6A | 0.8600 | C11—C16 | 1.390 (4) |
N6—H6B | 0.8600 | C11—C12 | 1.394 (4) |
O1—C2 | 1.237 (3) | C12—C13 | 1.389 (4) |
O2—C4 | 1.351 (4) | C13—C14 | 1.367 (4) |
O2—H2A | 0.8200 | C13—H13 | 0.9300 |
O3—C10 | 1.225 (3) | C14—C15 | 1.381 (5) |
O4—C12 | 1.359 (3) | C14—H14 | 0.9300 |
O4—H4 | 0.8200 | C15—C16 | 1.371 (4) |
O5—H5D | 0.8496 | C15—H15 | 0.9300 |
O5—H5B | 0.8500 | C16—H16 | 0.9300 |
C1—N1—N2 | 122.6 (3) | C4—C5—H5A | 120.0 |
C1—N1—H1 | 118.7 | C5—C6—C7 | 120.9 (3) |
N2—N1—H1 | 118.7 | C5—C6—H6 | 119.5 |
C2—N2—N1 | 120.9 (3) | C7—C6—H6 | 119.5 |
C2—N2—H2 | 119.5 | C8—C7—C6 | 119.5 (3) |
N1—N2—H2 | 119.5 | C8—C7—H7 | 120.3 |
C1—N3—H3A | 120.0 | C6—C7—H7 | 120.3 |
C1—N3—H3B | 120.0 | C7—C8—C3 | 121.4 (3) |
H3A—N3—H3B | 120.0 | C7—C8—H8 | 119.3 |
C9—N4—N5 | 121.4 (3) | C3—C8—H8 | 119.3 |
C9—N4—H4' | 119.3 | N6—C9—N4 | 118.4 (3) |
N5—N4—H4' | 119.3 | N6—C9—S2 | 123.2 (3) |
C10—N5—N4 | 120.5 (3) | N4—C9—S2 | 118.4 (3) |
C10—N5—H5 | 119.7 | O3—C10—N5 | 121.3 (3) |
N4—N5—H5 | 119.7 | O3—C10—C11 | 121.8 (3) |
C9—N6—H6A | 120.0 | N5—C10—C11 | 116.8 (3) |
C9—N6—H6B | 120.0 | C16—C11—C12 | 118.1 (3) |
H6A—N6—H6B | 120.0 | C16—C11—C10 | 116.9 (3) |
C4—O2—H2A | 109.5 | C12—C11—C10 | 125.0 (3) |
C12—O4—H4 | 109.5 | O4—C12—C13 | 121.3 (3) |
H5D—O5—H5B | 129.4 | O4—C12—C11 | 118.8 (3) |
N3—C1—N1 | 119.1 (3) | C13—C12—C11 | 119.9 (3) |
N3—C1—S1 | 122.3 (3) | C14—C13—C12 | 120.6 (3) |
N1—C1—S1 | 118.6 (3) | C14—C13—H13 | 119.7 |
O1—C2—N2 | 119.4 (3) | C12—C13—H13 | 119.7 |
O1—C2—C3 | 122.4 (3) | C13—C14—C15 | 120.2 (3) |
N2—C2—C3 | 118.2 (3) | C13—C14—H14 | 119.9 |
C8—C3—C4 | 118.1 (3) | C15—C14—H14 | 119.9 |
C8—C3—C2 | 123.4 (3) | C16—C15—C14 | 119.5 (3) |
C4—C3—C2 | 118.5 (3) | C16—C15—H15 | 120.3 |
O2—C4—C5 | 117.2 (3) | C14—C15—H15 | 120.3 |
O2—C4—C3 | 122.7 (3) | C15—C16—C11 | 121.7 (3) |
C5—C4—C3 | 120.0 (3) | C15—C16—H16 | 119.2 |
C6—C5—C4 | 120.1 (3) | C11—C16—H16 | 119.2 |
C6—C5—H5A | 120.0 |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2···S1i | 0.86 | 2.58 | 3.361 (3) | 151 |
N5—H5···S1ii | 0.86 | 2.83 | 3.404 (3) | 125 |
N6—H6A···O2iii | 0.86 | 2.16 | 2.984 (3) | 160 |
N6—H6B···S2iv | 0.86 | 2.85 | 3.647 (3) | 156 |
O4—H4···O1ii | 0.82 | 1.93 | 2.724 (3) | 162 |
O5—H5B···O5v | 0.85 | 1.95 | 2.728 (10) | 152 |
N3—H3A···O3 | 0.86 | 2.12 | 2.918 (3) | 154 |
N3—H3B···O5 | 0.86 | 2.30 | 3.110 (5) | 156 |
N5—H5···O4 | 0.86 | 1.99 | 2.629 (3) | 130 |
O2—H2A···O1 | 0.82 | 1.83 | 2.552 (3) | 146 |
O5—H5D···S1 | 0.85 | 2.66 | 3.398 (4) | 147 |
Symmetry codes: (i) −x+1, −y, −z+1; (ii) x+1, y, z; (iii) x+1/2, −y+1/2, z−1/2; (iv) −x+2, −y, −z; (v) −x+1, −y, −z. |
Experimental details
Crystal data | |
Chemical formula | C16H20N6O5S2 |
Mr | 440.50 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 298 |
a, b, c (Å) | 9.0718 (11), 21.608 (2), 10.1035 (13) |
β (°) | 90.173 (1) |
V (Å3) | 1980.5 (4) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.31 |
Crystal size (mm) | 0.45 × 0.20 × 0.17 |
Data collection | |
Diffractometer | Bruker SMART APEX CCD area-detector |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.873, 0.949 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 9862, 3487, 2202 |
Rint | 0.041 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.047, 0.122, 1.01 |
No. of reflections | 3487 |
No. of parameters | 262 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.37, −0.33 |
Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2···S1i | 0.86 | 2.58 | 3.361 (3) | 151.4 |
N5—H5···S1ii | 0.86 | 2.83 | 3.404 (3) | 125.4 |
N6—H6A···O2iii | 0.86 | 2.16 | 2.984 (3) | 160.3 |
N6—H6B···S2iv | 0.86 | 2.85 | 3.647 (3) | 155.5 |
O4—H4···O1ii | 0.82 | 1.93 | 2.724 (3) | 162.3 |
O5—H5B···O5v | 0.85 | 1.95 | 2.728 (10) | 151.7 |
N3—H3A···O3 | 0.86 | 2.12 | 2.918 (3) | 153.7 |
N3—H3B···O5 | 0.86 | 2.30 | 3.110 (5) | 156.3 |
N5—H5···O4 | 0.86 | 1.99 | 2.629 (3) | 130.3 |
O2—H2A···O1 | 0.82 | 1.83 | 2.552 (3) | 145.6 |
O5—H5D···S1 | 0.85 | 2.66 | 3.398 (4) | 146.7 |
Symmetry codes: (i) −x+1, −y, −z+1; (ii) x+1, y, z; (iii) x+1/2, −y+1/2, z−1/2; (iv) −x+2, −y, −z; (v) −x+1, −y, −z. |
Acknowledgements
The authors acknowledge the financial support of the Foundation of Binzhou University (grant No. BZXYQNLG200501).
References
Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Desai, N. C., Shukla, H. K., Paresh, B. P. & Thaker, K. A. (1984). J. Indian Chem. Soc. pp. 455–457. Google Scholar
Gors, C., Baert, F., Henichart, J. P. & Houssin, R. (1979). J. Mol. Struct. 55, 223–233. CSD CrossRef CAS Web of Science Google Scholar
Jin, L.-F. (2007). Acta Cryst. E63, o3465. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Shukla, H. K., Desai, N. C., Astik, R. R. & Thaker, K. A. (1984). J. Indian Chem. Soc. pp. 168–196. Google Scholar
This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
Thiosemicarbazide compounds exhibit various biological activities such as anti-bacterial, anti-fungal and especially anti-tuberculosis (Shukla et al., 1984; Desai et al., 1984). Herewith we present the title compound (I), a new thiosemicarbazide compound.
The asymmetric unit of (I) contains two independent molecules and one crystalline water molecule (Fig. 1). The bond lengths and angles are normal and comparable to the values observed in similar compounds (Gors et al., 1979; Jin, 2007). In two independent molecules, the benzene rings and the thiosemicarbazone fragments (C/N/N) are twisted at 9.2 (3)° and 18.5 (3)°, respectively.
In the crystal structure, the three-dimensional network structure was formed by the intermolecular N—H···O, N—H···S and O—H···O hydrogen bonds (Table 1).