organic compounds
2-[(E)-2-Hydroxy-3-methoxybenzylidene]-N-methylhydrazinecarbothioamide
aDepartment of Chemistry, Sri Krishna Institute of Technology, Bangalore 560 090, India, bDepartment of Chemistry, S. D. M. College of Engineering and Technology, Dharwad 580 002, India, cDepartment of Inorganic and Physical Chemistry, Indian Institute of Science, Bangalore 560 012, India, and dDepartment of Chemistry, M. S. Ramaiah Institute of Technology, Bangalore 560 054, Karnataka, India
*Correspondence e-mail: muralikp21@gmail.com
In the 11H15N3O2S, molecules are linked by pairs of N—H⋯O and O—H⋯S hydrogen, forming inversion dimers. These dimers are linked by N—H⋯S hydrogen bonds, forming double-stranded chains propagating along the b-axis direction. The two C atoms of the end chain of the molecule are disordered over two sets os sites [occupancy ratio 0.574 (9):0.426 (9)].
of the title compound, CRelated literature
For related structures, see: Joseph et al. (2006); Ren-Gao Zhao et al.(2008). For the biological activity of thiosemicarbazone see: Kasuga et al. (2003); Murali et al. (2008, 2009); Paterson & Donnelly (2011).
Experimental
Crystal data
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Refinement
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Data collection: APEX2 (Bruker, 2006); cell SAINT (Bruker, 2006); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012).
Supporting information
https://doi.org/10.1107/S1600536812049847/gw2126sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812049847/gw2126Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S1600536812049847/gw2126Isup3.cml
The title compound (I)was synthesized by the reaction of 2-hydroxy-3-methoxy benzaldehyde (10 g, 0.1 mol) in 250 ml round bottom flask, 5% acetic acid-water solution of 4 N-methyl hydrazinecarbothioamide (0.1 mol) in ethanol solution and refluxed on a steam bath for 30–45 minutes. The crystalline product which formed was collected by filtration, washed several times with hot water and, then ether, finally dried in vacuo. Then good quality crystals (I)were obtained in a 1:1 mixture of ethanol and n-hexane.
The hydrogen atoms were located with the help of difference fourier maps. Hydrogen atoms for C7, C6 were positioned geometrically and refined using a riding model.
The end group of N-Et was disordered and modelled with the help of part command. The major component i.e. N3–C10–C11 is depicted in the ORTEP diagram. since this group is diordered over two positions, isotropic
is done for these 3 atoms. SADI and DFIX commands were used to model the disordered atoms. The hydrogen atoms were fixed for these atoms.There are two reflections missing from the fcf file according to check
which may be at high angle beyond the limiting sphere and not possible for recording despite the fact the data was recollected with another crystal.Thiosemicarbazones emerged an important class of sulfur and nitrogen containing Schiff-bases due to their chemistry and potentially beneficial biological activities, such as antitumor,antibacterial, antiviral and antimalarial activities (Kasuga et al., 2003; Paterson & Donnelly, 2011). In a continuation of our studies on thiosemicarbazone Schiff-bases, we report the synthesis and
of the title compound, (I).In (I) (Fig. 1), all bond lengths and angles are normal and in a good agreement with those found in the literature (Joseph et al., 2006).There is one molecule in the assymetric unit with the end atoms thermally disordered. This molecule exhibits intermolecular N—H···O and O—H···S hydrogen bonds (Table 2) forming a dimer along b axis. These dimers give rise to a zigzag pattern seen along c axis. Further the molecules are packed by weak π···π interactions [centroid–centroid distance 4.495 (5) Å]
For related structures, see: Joseph et al. (2006); Ren-Gao Zhao et al.(2008). For the biological activity of thiosemicarbazone
see: Kasuga et al. (2003); Murali et al. (2008, 2009); Paterson & Donnelly (2011).Data collection: APEX2 (Bruker, 2006); cell
SAINT (Bruker, 2006); data reduction: SAINT (Bruker, 2006); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012).C11H15N3O2S | F(000) = 536 |
Mr = 253.32 | Dx = 1.363 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 1499 reflections |
a = 13.251 (6) Å | θ = 2.6–25.6° |
b = 6.185 (3) Å | µ = 0.26 mm−1 |
c = 16.380 (8) Å | T = 293 K |
β = 113.153 (7)° | Rectangular plate like, yellow |
V = 1234.4 (11) Å3 | 0.26 × 0.09 × 0.05 mm |
Z = 4 |
Bruker APEXII CCD diffractometer | 2433 independent reflections |
Radiation source: fine-focus sealed tube | 1666 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.030 |
Detector resolution: 0.3 pixels mm-1 | θmax = 26.0°, θmin = 1.7° |
φ and ω scans | h = −16→16 |
Absorption correction: multi-scan (SADABS; Bruker, 2006) | k = −6→7 |
Tmin = 0.936, Tmax = 0.987 | l = −20→20 |
7373 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)] = 0.064 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.180 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.06 | w = 1/[σ2(Fo2) + (0.0756P)2 + 1.2001P] where P = (Fo2 + 2Fc2)/3 |
2433 reflections | (Δ/σ)max < 0.001 |
175 parameters | Δρmax = 0.46 e Å−3 |
4 restraints | Δρmin = −0.37 e Å−3 |
C11H15N3O2S | V = 1234.4 (11) Å3 |
Mr = 253.32 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 13.251 (6) Å | µ = 0.26 mm−1 |
b = 6.185 (3) Å | T = 293 K |
c = 16.380 (8) Å | 0.26 × 0.09 × 0.05 mm |
β = 113.153 (7)° |
Bruker APEXII CCD diffractometer | 2433 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2006) | 1666 reflections with I > 2σ(I) |
Tmin = 0.936, Tmax = 0.987 | Rint = 0.030 |
7373 measured reflections |
R[F2 > 2σ(F2)] = 0.064 | 4 restraints |
wR(F2) = 0.180 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.06 | Δρmax = 0.46 e Å−3 |
2433 reflections | Δρmin = −0.37 e Å−3 |
175 parameters |
Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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) | |
S1 | 0.87523 (8) | 0.71851 (17) | 0.56230 (8) | 0.0642 (4) | |
O1 | 0.37812 (19) | 0.2015 (4) | 0.55013 (16) | 0.0483 (6) | |
O2 | 0.28859 (18) | −0.1250 (4) | 0.60039 (16) | 0.0515 (7) | |
N1 | 0.7027 (2) | 0.2534 (4) | 0.60644 (18) | 0.0419 (7) | |
N2 | 0.7343 (2) | 0.4427 (5) | 0.5791 (2) | 0.0462 (7) | |
C1 | 0.5554 (2) | 0.0466 (5) | 0.61505 (19) | 0.0355 (7) | |
C2 | 0.4438 (2) | 0.0358 (5) | 0.59547 (19) | 0.0356 (7) | |
C3 | 0.3996 (3) | −0.1393 (5) | 0.6244 (2) | 0.0393 (7) | |
C4 | 0.4666 (3) | −0.3038 (6) | 0.6715 (2) | 0.0457 (8) | |
C5 | 0.5792 (3) | −0.2945 (6) | 0.6909 (2) | 0.0473 (8) | |
C6 | 0.6224 (3) | −0.1240 (5) | 0.6625 (2) | 0.0420 (8) | |
H6 | 0.6972 | −0.1211 | 0.6748 | 0.050* | |
C7 | 0.2363 (3) | −0.2905 (7) | 0.6292 (3) | 0.0617 (11) | |
H7A | 0.2530 | −0.4284 | 0.6107 | 0.093* | |
H7B | 0.1583 | −0.2680 | 0.6036 | 0.093* | |
H7C | 0.2621 | −0.2871 | 0.6927 | 0.093* | |
C8 | 0.5999 (3) | 0.2336 (5) | 0.5868 (2) | 0.0386 (7) | |
C9 | 0.8392 (3) | 0.4794 (6) | 0.5909 (2) | 0.0491 (9) | |
N3 | 0.9010 (4) | 0.2968 (11) | 0.6089 (5) | 0.0524 (17)* | 0.574 (9) |
H3 | 0.8756 | 0.1678 | 0.5955 | 0.063* | 0.574 (9) |
C10 | 1.0329 (6) | 0.3596 (12) | 0.6605 (6) | 0.076 (3)* | 0.574 (9) |
H10A | 1.0552 | 0.4659 | 0.6273 | 0.092* | 0.574 (9) |
H10B | 1.0491 | 0.4138 | 0.7199 | 0.092* | 0.574 (9) |
C11 | 1.0867 (7) | 0.1453 (13) | 0.6627 (7) | 0.079 (3)* | 0.574 (9) |
H11A | 1.0750 | 0.0528 | 0.7052 | 0.119* | 0.574 (9) |
H11B | 1.1641 | 0.1661 | 0.6793 | 0.119* | 0.574 (9) |
H11C | 1.0556 | 0.0797 | 0.6050 | 0.119* | 0.574 (9) |
N3A | 0.9128 (5) | 0.3405 (12) | 0.6420 (6) | 0.043 (2)* | 0.426 (9) |
H3A | 0.9109 | 0.2887 | 0.6901 | 0.051* | 0.426 (9) |
C10A | 1.0095 (7) | 0.2744 (17) | 0.6053 (6) | 0.065 (3)* | 0.426 (9) |
H10C | 0.9888 | 0.1537 | 0.5641 | 0.078* | 0.426 (9) |
H10D | 1.0334 | 0.3959 | 0.5799 | 0.078* | 0.426 (9) |
C11A | 1.0909 (11) | 0.213 (3) | 0.6964 (8) | 0.111 (5)* | 0.426 (9) |
H11D | 1.0844 | 0.3111 | 0.7395 | 0.167* | 0.426 (9) |
H11E | 1.1639 | 0.2207 | 0.6977 | 0.167* | 0.426 (9) |
H11F | 1.0763 | 0.0684 | 0.7100 | 0.167* | 0.426 (9) |
H1 | 0.309 (3) | 0.176 (6) | 0.535 (2) | 0.055 (11)* | |
H2 | 0.687 (3) | 0.534 (6) | 0.556 (2) | 0.048 (11)* | |
H4 | 0.435 (3) | −0.420 (6) | 0.688 (2) | 0.050 (10)* | |
H5 | 0.634 (3) | −0.414 (6) | 0.726 (2) | 0.060 (10)* | |
H8 | 0.553 (3) | 0.336 (5) | 0.557 (2) | 0.040 (9)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0450 (6) | 0.0550 (6) | 0.0933 (8) | −0.0108 (4) | 0.0280 (5) | 0.0119 (5) |
O1 | 0.0348 (13) | 0.0452 (14) | 0.0638 (16) | 0.0000 (11) | 0.0181 (12) | 0.0143 (12) |
O2 | 0.0413 (13) | 0.0519 (15) | 0.0639 (15) | −0.0080 (11) | 0.0236 (12) | 0.0098 (12) |
N1 | 0.0391 (15) | 0.0401 (15) | 0.0505 (16) | −0.0012 (12) | 0.0217 (13) | 0.0044 (13) |
N2 | 0.0349 (15) | 0.0393 (16) | 0.066 (2) | 0.0004 (13) | 0.0212 (14) | 0.0096 (15) |
C1 | 0.0404 (17) | 0.0351 (17) | 0.0342 (16) | −0.0023 (13) | 0.0181 (14) | −0.0020 (13) |
C2 | 0.0396 (17) | 0.0325 (16) | 0.0359 (16) | 0.0003 (13) | 0.0160 (14) | 0.0013 (13) |
C3 | 0.0423 (18) | 0.0400 (18) | 0.0408 (17) | −0.0068 (15) | 0.0218 (15) | −0.0035 (15) |
C4 | 0.057 (2) | 0.0352 (18) | 0.051 (2) | −0.0042 (16) | 0.0276 (18) | 0.0058 (15) |
C5 | 0.053 (2) | 0.0410 (19) | 0.051 (2) | 0.0068 (16) | 0.0245 (17) | 0.0094 (16) |
C6 | 0.0388 (17) | 0.0431 (18) | 0.0468 (19) | 0.0040 (15) | 0.0197 (15) | 0.0012 (15) |
C7 | 0.055 (2) | 0.063 (3) | 0.075 (3) | −0.0192 (19) | 0.035 (2) | 0.004 (2) |
C8 | 0.0355 (17) | 0.0373 (17) | 0.0426 (18) | −0.0004 (15) | 0.0151 (14) | 0.0042 (15) |
C9 | 0.0367 (18) | 0.051 (2) | 0.059 (2) | −0.0024 (16) | 0.0194 (16) | 0.0060 (17) |
S1—C9 | 1.676 (4) | C7—H7C | 0.9600 |
O1—C2 | 1.360 (4) | C8—H8 | 0.89 (3) |
O1—H1 | 0.87 (4) | C9—N3A | 1.322 (8) |
O2—C3 | 1.367 (4) | C9—N3 | 1.358 (7) |
O2—C7 | 1.416 (4) | N3—C10 | 1.661 (8) |
N1—C8 | 1.277 (4) | N3—H3 | 0.8600 |
N1—N2 | 1.376 (4) | C10—C11 | 1.499 (7) |
N2—C9 | 1.346 (4) | C10—H10A | 0.9700 |
N2—H2 | 0.82 (3) | C10—H10B | 0.9700 |
C1—C2 | 1.387 (4) | C11—H11A | 0.9600 |
C1—C6 | 1.401 (4) | C11—H11B | 0.9600 |
C1—C8 | 1.454 (4) | C11—H11C | 0.9600 |
C2—C3 | 1.399 (4) | N3A—C10A | 1.667 (8) |
C3—C4 | 1.371 (5) | N3A—H3A | 0.8600 |
C4—C5 | 1.399 (5) | C10A—C11A | 1.506 (7) |
C4—H4 | 0.93 (4) | C10A—H10C | 0.9700 |
C5—C6 | 1.366 (5) | C10A—H10D | 0.9700 |
C5—H5 | 1.04 (4) | C11A—H11D | 0.9600 |
C6—H6 | 0.9300 | C11A—H11E | 0.9600 |
C7—H7A | 0.9600 | C11A—H11F | 0.9600 |
C7—H7B | 0.9600 | ||
C2—O1—H1 | 113 (3) | N1—C8—H8 | 121 (2) |
C3—O2—C7 | 118.0 (3) | C1—C8—H8 | 118 (2) |
C8—N1—N2 | 115.5 (3) | N3A—C9—N2 | 116.4 (4) |
C9—N2—N1 | 121.7 (3) | N2—C9—N3 | 113.1 (4) |
C9—N2—H2 | 120 (2) | N3A—C9—S1 | 122.0 (4) |
N1—N2—H2 | 118 (2) | N2—C9—S1 | 120.0 (3) |
C2—C1—C6 | 118.5 (3) | N3—C9—S1 | 125.5 (3) |
C2—C1—C8 | 119.6 (3) | C9—N3—C10 | 109.9 (5) |
C6—C1—C8 | 121.9 (3) | C9—N3—H3 | 125.1 |
O1—C2—C1 | 119.0 (3) | C10—N3—H3 | 125.1 |
O1—C2—C3 | 120.3 (3) | C11—C10—N3 | 101.6 (6) |
C1—C2—C3 | 120.6 (3) | C11—C10—H10A | 111.4 |
O2—C3—C4 | 126.5 (3) | N3—C10—H10A | 111.4 |
O2—C3—C2 | 113.5 (3) | C11—C10—H10B | 111.4 |
C4—C3—C2 | 120.0 (3) | N3—C10—H10B | 111.4 |
C3—C4—C5 | 119.6 (3) | H10A—C10—H10B | 109.3 |
C3—C4—H4 | 118 (2) | C9—N3A—C10A | 114.2 (6) |
C5—C4—H4 | 122 (2) | C9—N3A—H3A | 122.9 |
C6—C5—C4 | 120.4 (3) | C10A—N3A—H3A | 122.9 |
C6—C5—H5 | 116 (2) | C11A—C10A—N3A | 93.3 (9) |
C4—C5—H5 | 123 (2) | C11A—C10A—H10C | 113.1 |
C5—C6—C1 | 120.7 (3) | N3A—C10A—H10C | 113.1 |
C5—C6—H6 | 119.6 | C11A—C10A—H10D | 113.1 |
C1—C6—H6 | 119.6 | N3A—C10A—H10D | 113.1 |
O2—C7—H7A | 109.5 | H10C—C10A—H10D | 110.4 |
O2—C7—H7B | 109.5 | C10A—C11A—H11D | 109.5 |
H7A—C7—H7B | 109.5 | C10A—C11A—H11E | 109.5 |
O2—C7—H7C | 109.5 | H11D—C11A—H11E | 109.5 |
H7A—C7—H7C | 109.5 | C10A—C11A—H11F | 109.5 |
H7B—C7—H7C | 109.5 | H11D—C11A—H11F | 109.5 |
N1—C8—C1 | 121.5 (3) | H11E—C11A—H11F | 109.5 |
C8—N1—N2—C9 | −176.1 (3) | C8—C1—C6—C5 | 177.8 (3) |
C6—C1—C2—O1 | 179.4 (3) | N2—N1—C8—C1 | −177.1 (3) |
C8—C1—C2—O1 | −0.1 (4) | C2—C1—C8—N1 | 177.3 (3) |
C6—C1—C2—C3 | 1.5 (4) | C6—C1—C8—N1 | −2.2 (5) |
C8—C1—C2—C3 | −178.0 (3) | N1—N2—C9—N3A | −10.2 (6) |
C7—O2—C3—C4 | 2.6 (5) | N1—N2—C9—N3 | 16.6 (6) |
C7—O2—C3—C2 | −177.8 (3) | N1—N2—C9—S1 | −176.2 (3) |
O1—C2—C3—O2 | 1.6 (4) | N3A—C9—N3—C10 | −54.4 (10) |
C1—C2—C3—O2 | 179.5 (3) | N2—C9—N3—C10 | −157.7 (5) |
O1—C2—C3—C4 | −178.8 (3) | S1—C9—N3—C10 | 35.9 (8) |
C1—C2—C3—C4 | −0.9 (5) | C9—N3—C10—C11 | −172.4 (6) |
O2—C3—C4—C5 | −180.0 (3) | N2—C9—N3A—C10A | 139.6 (6) |
C2—C3—C4—C5 | 0.5 (5) | N3—C9—N3A—C10A | 51.5 (9) |
C3—C4—C5—C6 | −0.7 (5) | S1—C9—N3A—C10A | −54.8 (9) |
C4—C5—C6—C1 | 1.3 (5) | C9—N3A—C10A—C11A | 155.8 (9) |
C2—C1—C6—C5 | −1.7 (5) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···S1i | 0.87 (4) | 2.42 (4) | 3.169 (3) | 145 (3) |
N2—H2···O1i | 0.82 (3) | 2.29 (4) | 3.010 (4) | 147 (3) |
Symmetry code: (i) −x+1, −y+1, −z+1. |
Experimental details
Crystal data | |
Chemical formula | C11H15N3O2S |
Mr | 253.32 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 293 |
a, b, c (Å) | 13.251 (6), 6.185 (3), 16.380 (8) |
β (°) | 113.153 (7) |
V (Å3) | 1234.4 (11) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.26 |
Crystal size (mm) | 0.26 × 0.09 × 0.05 |
Data collection | |
Diffractometer | Bruker APEXII CCD |
Absorption correction | Multi-scan (SADABS; Bruker, 2006) |
Tmin, Tmax | 0.936, 0.987 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 7373, 2433, 1666 |
Rint | 0.030 |
(sin θ/λ)max (Å−1) | 0.617 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.064, 0.180, 1.06 |
No. of reflections | 2433 |
No. of parameters | 175 |
No. of restraints | 4 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.46, −0.37 |
Computer programs: APEX2 (Bruker, 2006), SAINT (Bruker, 2006), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 2012), WinGX (Farrugia, 2012).
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···S1i | 0.87 (4) | 2.42 (4) | 3.169 (3) | 145 (3) |
N2—H2···O1i | 0.82 (3) | 2.29 (4) | 3.010 (4) | 147 (3) |
Symmetry code: (i) −x+1, −y+1, −z+1. |
Acknowledgements
The work was financed by a grant (project No: VTU/Aca./2010–11/A–9/11341) from Visvesvaraya Technological University. YPP thanks the CSIR, India, for a fellowship.
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Thiosemicarbazones emerged an important class of sulfur and nitrogen containing Schiff-bases due to their chemistry and potentially beneficial biological activities, such as antitumor,antibacterial, antiviral and antimalarial activities (Kasuga et al., 2003; Paterson & Donnelly, 2011). In a continuation of our studies on thiosemicarbazone Schiff-bases, we report the synthesis and crystal structure of the title compound, (I).
In (I) (Fig. 1), all bond lengths and angles are normal and in a good agreement with those found in the literature (Joseph et al., 2006).There is one molecule in the assymetric unit with the end atoms thermally disordered. This molecule exhibits intermolecular N—H···O and O—H···S hydrogen bonds (Table 2) forming a dimer along b axis. These dimers give rise to a zigzag pattern seen along c axis. Further the molecules are packed by weak π···π interactions [centroid–centroid distance 4.495 (5) Å]