Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807025548/rz2142sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807025548/rz2142Isup2.hkl |
CCDC reference: 651539
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.003 Å
- R factor = 0.044
- wR factor = 0.126
- Data-to-parameter ratio = 18.9
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT029_ALERT_3_B _diffrn_measured_fraction_theta_full Low ....... 0.94
Alert level C REFLT03_ALERT_3_C Reflection count < 95% complete From the CIF: _diffrn_reflns_theta_max 28.74 From the CIF: _diffrn_reflns_theta_full 28.74 From the CIF: _reflns_number_total 4293 TEST2: Reflns within _diffrn_reflns_theta_max Count of symmetry unique reflns 4546 Completeness (_total/calc) 94.43%
Alert level G PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 2 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 2 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
The title compound was prepared by the reaction of 3,5-dimethoxy bezohydrazide (3.92 g, 20 mmol) and 2-methoxyphenyl isothiocyanate (3.3 g, 20 mmol). Single crystals suitable for X-ray measurements were obtained by slow evaporation of an ethanol/water solution (60: 40 v/v) at room temperature (yield: 80%; m.p. 435–437 K).
H atoms were positioned geometrically, with N—H = 0.86 Å and C—H = 0.93–0.96 Å, and constrained to ride on their parent atoms, with Uiso(H) = 1.2 Ueq(C, N) or 1.2 Ueq(C) for methyl groups.
Thiosemicarbazide is interesting because of the formation of complexes with biological activities (Shen et al., 1998). Some substituted thiourea derivatives have shown interesting biological effects, including anti-HIV properties (Mao et al., 1999), and thiourea derivatives have also been successfully screened for various biological actions (Antholine & Taketa, 1982). As a ligand with potential S– and N-atom donors, thiosemicarbazide is interesting because of the structural chemistry of its multifunctional coordination modes (N-monodentate, S-monodentate or N,S-bidentate). In order to investigate further this kind of ligand, we synthesized the title compound and describe its structure here.
In the molecule (Fig. 1), the bond lengths and angles are in normal ranges (Allen et al., 1987; Ji et al., 2002). Selected bond distances and angles within the thiosemicarbazide group are quoted in Table 1. The thiosemicarbazide group is approximately planar (maximum displacement 0.133 (2) Å for atom N2) and forms dihedral angles of 33.03 (6) and 45.48 (5)° with the benzene rings. The dihedral angle between the benzene rings is 56.29 (6)°. The molecular structure is stabilized by intramolecular N—H···O, N—H···N and C—H···S hydrogen bonds (Table 2). Intermolecular N—H···O, N—H···S, C—H···S, C—H···O hydrogen interactions link the molecules into an extended three-dimensional network.
For general background see: Allen et al. (1987); Shen et al. (1998); Mao et al. (1999); Antholine & Taketa (1982); for literature on a related structure see: Ji et al. (2002).
Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1999); software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003).
C17H19N3O4S | F(000) = 760 |
Mr = 361.42 | Dx = 1.371 Mg m−3 |
Monoclinic, P21/c | Melting point: 435(2) K |
Hall symbol: -P 2ybc | Mo Kα radiation, λ = 0.71073 Å |
a = 15.371 (6) Å | Cell parameters from 1520 reflections |
b = 14.775 (6) Å | θ = 2.7–24.9° |
c = 7.904 (3) Å | µ = 0.21 mm−1 |
β = 102.835 (6)° | T = 293 K |
V = 1750.2 (12) Å3 | Block, colourless |
Z = 4 | 0.46 × 0.26 × 0.20 mm |
Bruker APEXII diffractometer | 4293 independent reflections |
Radiation source: rotating-anode generator | 3033 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.030 |
φ and ω scans | θmax = 28.7°, θmin = 1.9° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −20→20 |
Tmin = 0.904, Tmax = 0.960 | k = −19→19 |
13047 measured reflections | l = −10→10 |
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)] = 0.044 | H-atom parameters constrained |
wR(F2) = 0.127 | w = 1/[σ2(Fo2) + (0.0179P)2 + 0.3525P] where P = (Fo2 + 2Fc2)/3 |
S = 1.10 | (Δ/σ)max < 0.001 |
4293 reflections | Δρmax = 0.26 e Å−3 |
227 parameters | Δρmin = −0.32 e Å−3 |
0 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0132 (17) |
C17H19N3O4S | V = 1750.2 (12) Å3 |
Mr = 361.42 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 15.371 (6) Å | µ = 0.21 mm−1 |
b = 14.775 (6) Å | T = 293 K |
c = 7.904 (3) Å | 0.46 × 0.26 × 0.20 mm |
β = 102.835 (6)° |
Bruker APEXII diffractometer | 4293 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 3033 reflections with I > 2σ(I) |
Tmin = 0.904, Tmax = 0.960 | Rint = 0.030 |
13047 measured reflections |
R[F2 > 2σ(F2)] = 0.044 | 0 restraints |
wR(F2) = 0.127 | H-atom parameters constrained |
S = 1.10 | Δρmax = 0.26 e Å−3 |
4293 reflections | Δρmin = −0.32 e Å−3 |
227 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 | ||
S1 | 0.15553 (3) | 0.37817 (3) | 0.97813 (7) | 0.04962 (16) | |
O1 | 0.11298 (9) | 0.03948 (9) | 0.8952 (2) | 0.0637 (4) | |
O2 | 0.34541 (9) | −0.14431 (9) | 1.4113 (2) | 0.0639 (4) | |
O3 | 0.61762 (8) | −0.06156 (8) | 1.2608 (2) | 0.0558 (4) | |
O4 | 0.40068 (9) | 0.20133 (9) | 1.0677 (2) | 0.0607 (4) | |
N1 | 0.13745 (9) | 0.19931 (9) | 1.0337 (2) | 0.0487 (4) | |
H1B | 0.1633 | 0.1526 | 1.0874 | 0.058* | |
N2 | 0.26333 (9) | 0.26783 (9) | 1.1842 (2) | 0.0487 (4) | |
H2B | 0.2910 | 0.3156 | 1.2297 | 0.058* | |
N3 | 0.29958 (9) | 0.18262 (9) | 1.2322 (2) | 0.0470 (4) | |
H3B | 0.2777 | 0.1484 | 1.3004 | 0.056* | |
C1 | −0.01826 (12) | 0.24193 (14) | 0.9010 (3) | 0.0602 (5) | |
H1A | −0.0109 | 0.2990 | 0.9519 | 0.072* | |
C2 | −0.10062 (14) | 0.21636 (17) | 0.7993 (4) | 0.0757 (7) | |
H2A | −0.1484 | 0.2565 | 0.7820 | 0.091* | |
C3 | −0.11147 (16) | 0.13246 (18) | 0.7247 (4) | 0.0800 (7) | |
H3A | −0.1665 | 0.1163 | 0.6556 | 0.096* | |
C4 | −0.04169 (15) | 0.07148 (16) | 0.7508 (3) | 0.0713 (6) | |
H4A | −0.0498 | 0.0145 | 0.6997 | 0.086* | |
C5 | 0.04030 (12) | 0.09527 (13) | 0.8531 (3) | 0.0527 (5) | |
C6 | 0.05241 (11) | 0.18213 (12) | 0.9261 (2) | 0.0468 (4) | |
C7 | 0.35912 (11) | −0.00066 (11) | 1.2957 (2) | 0.0458 (4) | |
H7A | 0.3014 | 0.0118 | 1.3069 | 0.055* | |
C8 | 0.39811 (11) | −0.08474 (11) | 1.3456 (2) | 0.0458 (4) | |
C9 | 0.48417 (11) | −0.10345 (11) | 1.3312 (2) | 0.0452 (4) | |
H9A | 0.5097 | −0.1595 | 1.3649 | 0.054* | |
C10 | 0.53229 (10) | −0.03741 (11) | 1.2657 (2) | 0.0423 (4) | |
C11 | 0.49472 (10) | 0.04567 (11) | 1.2121 (2) | 0.0425 (4) | |
H11A | 0.5267 | 0.0888 | 1.1654 | 0.051* | |
C12 | 0.40784 (10) | 0.06380 (10) | 1.2293 (2) | 0.0401 (4) | |
C13 | 0.18429 (10) | 0.27610 (10) | 1.0656 (2) | 0.0398 (4) | |
C14 | 0.37060 (10) | 0.15494 (11) | 1.1684 (2) | 0.0417 (4) | |
C15 | 0.10394 (18) | −0.05097 (14) | 0.8277 (4) | 0.0806 (7) | |
H15A | 0.1593 | −0.0827 | 0.8656 | 0.121* | |
H15B | 0.0887 | −0.0489 | 0.7032 | 0.121* | |
H15C | 0.0577 | −0.0818 | 0.8690 | 0.121* | |
C16 | 0.38136 (16) | −0.23039 (14) | 1.4676 (3) | 0.0704 (6) | |
H16A | 0.3376 | −0.2652 | 1.5088 | 0.106* | |
H16B | 0.4333 | −0.2228 | 1.5597 | 0.106* | |
H16C | 0.3975 | −0.2614 | 1.3724 | 0.106* | |
C17 | 0.67315 (12) | 0.00578 (14) | 1.2084 (3) | 0.0586 (5) | |
H17A | 0.7308 | −0.0196 | 1.2098 | 0.088* | |
H17B | 0.6796 | 0.0561 | 1.2869 | 0.088* | |
H17C | 0.6463 | 0.0260 | 1.0932 | 0.088* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0436 (3) | 0.0354 (2) | 0.0669 (3) | 0.00322 (17) | 0.0061 (2) | 0.00655 (19) |
O1 | 0.0637 (9) | 0.0389 (7) | 0.0914 (12) | −0.0079 (6) | 0.0234 (8) | −0.0095 (7) |
O2 | 0.0528 (7) | 0.0463 (7) | 0.0977 (12) | 0.0047 (6) | 0.0273 (8) | 0.0188 (7) |
O3 | 0.0380 (6) | 0.0455 (7) | 0.0859 (10) | 0.0085 (5) | 0.0177 (6) | 0.0024 (6) |
O4 | 0.0609 (8) | 0.0430 (7) | 0.0833 (11) | 0.0051 (6) | 0.0272 (8) | 0.0127 (7) |
N1 | 0.0411 (8) | 0.0340 (7) | 0.0659 (11) | −0.0021 (6) | 0.0011 (7) | 0.0039 (6) |
N2 | 0.0387 (7) | 0.0315 (7) | 0.0704 (11) | 0.0051 (5) | 0.0000 (7) | −0.0020 (6) |
N3 | 0.0408 (7) | 0.0357 (7) | 0.0642 (10) | 0.0085 (6) | 0.0108 (7) | 0.0078 (6) |
C1 | 0.0420 (9) | 0.0507 (11) | 0.0848 (16) | −0.0022 (8) | 0.0077 (10) | 0.0057 (10) |
C2 | 0.0420 (11) | 0.0751 (15) | 0.103 (2) | −0.0069 (10) | 0.0004 (12) | 0.0210 (13) |
C3 | 0.0519 (12) | 0.0922 (18) | 0.0861 (18) | −0.0259 (12) | −0.0058 (12) | 0.0148 (14) |
C4 | 0.0697 (14) | 0.0672 (14) | 0.0735 (16) | −0.0310 (12) | 0.0083 (12) | −0.0093 (11) |
C5 | 0.0516 (10) | 0.0476 (10) | 0.0602 (13) | −0.0125 (8) | 0.0154 (9) | −0.0007 (8) |
C6 | 0.0393 (8) | 0.0426 (9) | 0.0568 (11) | −0.0077 (7) | 0.0070 (8) | 0.0033 (8) |
C7 | 0.0355 (8) | 0.0433 (9) | 0.0578 (12) | 0.0042 (7) | 0.0086 (8) | 0.0012 (8) |
C8 | 0.0425 (9) | 0.0393 (9) | 0.0546 (11) | 0.0003 (7) | 0.0089 (8) | 0.0023 (7) |
C9 | 0.0425 (9) | 0.0375 (8) | 0.0540 (11) | 0.0072 (7) | 0.0074 (8) | 0.0005 (7) |
C10 | 0.0353 (8) | 0.0403 (9) | 0.0500 (10) | 0.0048 (6) | 0.0068 (7) | −0.0047 (7) |
C11 | 0.0378 (8) | 0.0382 (8) | 0.0509 (11) | 0.0002 (6) | 0.0085 (7) | −0.0016 (7) |
C12 | 0.0360 (8) | 0.0365 (8) | 0.0453 (10) | 0.0030 (6) | 0.0038 (7) | −0.0018 (7) |
C13 | 0.0349 (8) | 0.0339 (8) | 0.0510 (10) | 0.0031 (6) | 0.0105 (7) | −0.0031 (7) |
C14 | 0.0361 (8) | 0.0359 (8) | 0.0499 (10) | 0.0015 (6) | 0.0029 (7) | −0.0013 (7) |
C15 | 0.0966 (17) | 0.0411 (11) | 0.116 (2) | −0.0178 (11) | 0.0493 (16) | −0.0168 (12) |
C16 | 0.0807 (15) | 0.0460 (11) | 0.0895 (18) | 0.0042 (10) | 0.0297 (13) | 0.0168 (11) |
C17 | 0.0419 (9) | 0.0575 (11) | 0.0784 (15) | 0.0035 (8) | 0.0177 (10) | 0.0062 (10) |
S1—C13 | 1.6769 (17) | C4—C5 | 1.383 (3) |
O1—C5 | 1.369 (2) | C4—H4A | 0.9300 |
O1—C15 | 1.434 (2) | C5—C6 | 1.403 (3) |
O2—C8 | 1.374 (2) | C7—C12 | 1.385 (2) |
O2—C16 | 1.418 (2) | C7—C8 | 1.398 (2) |
O3—C10 | 1.3681 (19) | C7—H7A | 0.9300 |
O3—C17 | 1.431 (2) | C8—C9 | 1.381 (2) |
O4—C14 | 1.217 (2) | C9—C10 | 1.392 (2) |
N1—C13 | 1.337 (2) | C9—H9A | 0.9300 |
N1—C6 | 1.415 (2) | C10—C11 | 1.382 (2) |
N1—H1B | 0.8600 | C11—C12 | 1.398 (2) |
N2—C13 | 1.365 (2) | C11—H11A | 0.9300 |
N2—N3 | 1.3949 (19) | C12—C14 | 1.500 (2) |
N2—H2B | 0.8600 | C15—H15A | 0.9600 |
N3—C14 | 1.363 (2) | C15—H15B | 0.9600 |
N3—H3B | 0.8600 | C15—H15C | 0.9600 |
C1—C6 | 1.380 (3) | C16—H16A | 0.9600 |
C1—C2 | 1.393 (3) | C16—H16B | 0.9600 |
C1—H1A | 0.9300 | C16—H16C | 0.9600 |
C2—C3 | 1.367 (4) | C17—H17A | 0.9600 |
C2—H2A | 0.9300 | C17—H17B | 0.9600 |
C3—C4 | 1.381 (3) | C17—H17C | 0.9600 |
C3—H3A | 0.9300 | ||
C5—O1—C15 | 117.66 (17) | C8—C9—C10 | 119.24 (15) |
C8—O2—C16 | 118.15 (15) | C8—C9—H9A | 120.4 |
C10—O3—C17 | 117.66 (14) | C10—C9—H9A | 120.4 |
C13—N1—C6 | 130.71 (15) | O3—C10—C11 | 124.11 (16) |
C13—N1—H1B | 114.6 | O3—C10—C9 | 114.81 (14) |
C6—N1—H1B | 114.6 | C11—C10—C9 | 121.07 (15) |
C13—N2—N3 | 120.56 (14) | C10—C11—C12 | 118.91 (16) |
C13—N2—H2B | 119.7 | C10—C11—H11A | 120.5 |
N3—N2—H2B | 119.7 | C12—C11—H11A | 120.5 |
C14—N3—N2 | 118.32 (15) | C7—C12—C11 | 120.92 (15) |
C14—N3—H3B | 120.8 | C7—C12—C14 | 122.62 (15) |
N2—N3—H3B | 120.8 | C11—C12—C14 | 116.45 (15) |
C6—C1—C2 | 119.7 (2) | N1—C13—N2 | 114.41 (14) |
C6—C1—H1A | 120.2 | N1—C13—S1 | 127.13 (13) |
C2—C1—H1A | 120.2 | N2—C13—S1 | 118.45 (12) |
C3—C2—C1 | 120.2 (2) | O4—C14—N3 | 121.67 (15) |
C3—C2—H2A | 119.9 | O4—C14—C12 | 122.85 (16) |
C1—C2—H2A | 119.9 | N3—C14—C12 | 115.48 (15) |
C2—C3—C4 | 120.7 (2) | O1—C15—H15A | 109.5 |
C2—C3—H3A | 119.6 | O1—C15—H15B | 109.5 |
C4—C3—H3A | 119.6 | H15A—C15—H15B | 109.5 |
C3—C4—C5 | 119.9 (2) | O1—C15—H15C | 109.5 |
C3—C4—H4A | 120.1 | H15A—C15—H15C | 109.5 |
C5—C4—H4A | 120.1 | H15B—C15—H15C | 109.5 |
O1—C5—C4 | 125.29 (19) | O2—C16—H16A | 109.5 |
O1—C5—C6 | 115.12 (16) | O2—C16—H16B | 109.5 |
C4—C5—C6 | 119.57 (19) | H16A—C16—H16B | 109.5 |
C1—C6—C5 | 119.90 (17) | O2—C16—H16C | 109.5 |
C1—C6—N1 | 124.34 (17) | H16A—C16—H16C | 109.5 |
C5—C6—N1 | 115.58 (16) | H16B—C16—H16C | 109.5 |
C12—C7—C8 | 118.96 (15) | O3—C17—H17A | 109.5 |
C12—C7—H7A | 120.5 | O3—C17—H17B | 109.5 |
C8—C7—H7A | 120.5 | H17A—C17—H17B | 109.5 |
O2—C8—C9 | 123.99 (16) | O3—C17—H17C | 109.5 |
O2—C8—C7 | 115.11 (15) | H17A—C17—H17C | 109.5 |
C9—C8—C7 | 120.89 (16) | H17B—C17—H17C | 109.5 |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1B···O1 | 0.86 | 2.28 | 2.595 (2) | 102 |
N1—H1B···N3 | 0.86 | 2.20 | 2.645 (2) | 112 |
C1—H1A···S1 | 0.93 | 2.78 | 3.292 (2) | 116 |
N2—H2B···O3i | 0.86 | 2.29 | 3.088 (2) | 155 |
N3—H3B···S1ii | 0.86 | 2.61 | 3.377 (2) | 149 |
C4—H4A···S1iii | 0.93 | 2.77 | 3.618 (3) | 152 |
C9—H9A···O4iv | 0.93 | 2.47 | 3.386 (2) | 170 |
Symmetry codes: (i) −x+1, y+1/2, −z+5/2; (ii) x, −y+1/2, z+1/2; (iii) −x, y−1/2, −z+3/2; (iv) −x+1, y−1/2, −z+5/2. |
Experimental details
Crystal data | |
Chemical formula | C17H19N3O4S |
Mr | 361.42 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 293 |
a, b, c (Å) | 15.371 (6), 14.775 (6), 7.904 (3) |
β (°) | 102.835 (6) |
V (Å3) | 1750.2 (12) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.21 |
Crystal size (mm) | 0.46 × 0.26 × 0.20 |
Data collection | |
Diffractometer | Bruker APEXII |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.904, 0.960 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 13047, 4293, 3033 |
Rint | 0.030 |
(sin θ/λ)max (Å−1) | 0.677 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.044, 0.127, 1.10 |
No. of reflections | 4293 |
No. of parameters | 227 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.26, −0.32 |
Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1999), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1999), SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003).
S1—C13 | 1.6769 (17) | N2—C13 | 1.365 (2) |
N1—C13 | 1.337 (2) | N2—N3 | 1.3949 (19) |
N1—C6 | 1.415 (2) | N3—C14 | 1.363 (2) |
C13—N1—C6 | 130.71 (15) | N3—N2—H2B | 119.7 |
C13—N2—N3 | 120.56 (14) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1B···O1 | 0.86 | 2.28 | 2.595 (2) | 102.1 |
N1—H1B···N3 | 0.86 | 2.20 | 2.645 (2) | 112.2 |
C1—H1A···S1 | 0.93 | 2.78 | 3.292 (2) | 115.8 |
N2—H2B···O3i | 0.86 | 2.29 | 3.088 (2) | 155.2 |
N3—H3B···S1ii | 0.86 | 2.61 | 3.377 (2) | 148.6 |
C4—H4A···S1iii | 0.93 | 2.77 | 3.618 (3) | 152.4 |
C9—H9A···O4iv | 0.93 | 2.47 | 3.386 (2) | 169.9 |
Symmetry codes: (i) −x+1, y+1/2, −z+5/2; (ii) x, −y+1/2, z+1/2; (iii) −x, y−1/2, −z+3/2; (iv) −x+1, y−1/2, −z+5/2. |
Thiosemicarbazide is interesting because of the formation of complexes with biological activities (Shen et al., 1998). Some substituted thiourea derivatives have shown interesting biological effects, including anti-HIV properties (Mao et al., 1999), and thiourea derivatives have also been successfully screened for various biological actions (Antholine & Taketa, 1982). As a ligand with potential S– and N-atom donors, thiosemicarbazide is interesting because of the structural chemistry of its multifunctional coordination modes (N-monodentate, S-monodentate or N,S-bidentate). In order to investigate further this kind of ligand, we synthesized the title compound and describe its structure here.
In the molecule (Fig. 1), the bond lengths and angles are in normal ranges (Allen et al., 1987; Ji et al., 2002). Selected bond distances and angles within the thiosemicarbazide group are quoted in Table 1. The thiosemicarbazide group is approximately planar (maximum displacement 0.133 (2) Å for atom N2) and forms dihedral angles of 33.03 (6) and 45.48 (5)° with the benzene rings. The dihedral angle between the benzene rings is 56.29 (6)°. The molecular structure is stabilized by intramolecular N—H···O, N—H···N and C—H···S hydrogen bonds (Table 2). Intermolecular N—H···O, N—H···S, C—H···S, C—H···O hydrogen interactions link the molecules into an extended three-dimensional network.