


Supporting information
![]() | Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807059788/ng2375sup1.cif |
![]() | Structure factor file (CIF format) https://doi.org/10.1107/S1600536807059788/ng2375Isup2.hkl |
CCDC reference: 674679
A mixture of 1-(4-methoxyphenyl)ethanone (1.5 g, 0.01 mol) and hydrazinecarbothioamide (0.91 g, 0.01 mol) in 15 ml of absolute ethanol containing 2 drops of 4 M sulfuric acid was refluxed for about 3 h. On cooling, the solid separated was filtered and recrystallized from ethyl acetate (m.p.: 448–450 K). Analysis found: C 53.70, H 5.83, N 18.76, S 14.31%; C10H13N3OS requires: C 53.79, H 5.87, N 18.82, S 14.36%.
H atoms were found in a difference map, but they were geometrically positioned and refined with fixed individual displacement parameters [U(H) = 1.2 Ueq(C) or U(H) = 1.5 Ueq(Cmethyl)] using a riding model with Caromatic—H = 0.95 Å, Cmethyl—H = 0.98 Å and N—H = 0.88 Å The methyl groups were allowed to rotate but not to tip. The crystal was a non-merohedral twin (twin law -1 0 0/0 - 1 0/0.85 0 1) with a contribution of 66.3 (3)% of the main component.
Data collection: X-AREA (Stoe & Cie, 2001); cell refinement: X-AREA (Stoe & Cie, 2001); data reduction: X-AREA (Stoe & Cie, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in SHELXTL-Plus (Sheldrick, 1991); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).
C10H13N3OS | F(000) = 944 |
Mr = 223.29 | Dx = 1.315 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 14.3548 (9) Å | Cell parameters from 30258 reflections |
b = 8.4141 (5) Å | θ = 2.8–26.2° |
c = 19.6562 (13) Å | µ = 0.27 mm−1 |
β = 108.123 (5)° | T = 173 K |
V = 2256.4 (3) Å3 | Plate, yellow |
Z = 8 | 0.31 × 0.25 × 0.18 mm |
Stoe IPDSII two-circle diffractometer | 4478 independent reflections |
Radiation source: fine-focus sealed tube | 3571 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.082 |
ω scans | θmax = 26.3°, θmin = 2.7° |
Absorption correction: multi-scan (MULABS; Spek, 2003; Blessing, 1995) | h = −17→16 |
Tmin = 0.923, Tmax = 0.954 | k = −10→10 |
42568 measured reflections | l = −12→24 |
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)] = 0.079 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.240 | H-atom parameters constrained |
S = 1.06 | w = 1/[σ2(Fo2) + (0.1562P)2 + 4.346P] where P = (Fo2 + 2Fc2)/3 |
4478 reflections | (Δ/σ)max = 0.001 |
282 parameters | Δρmax = 0.79 e Å−3 |
0 restraints | Δρmin = −0.48 e Å−3 |
C10H13N3OS | V = 2256.4 (3) Å3 |
Mr = 223.29 | Z = 8 |
Monoclinic, P21/c | Mo Kα radiation |
a = 14.3548 (9) Å | µ = 0.27 mm−1 |
b = 8.4141 (5) Å | T = 173 K |
c = 19.6562 (13) Å | 0.31 × 0.25 × 0.18 mm |
β = 108.123 (5)° |
Stoe IPDSII two-circle diffractometer | 4478 independent reflections |
Absorption correction: multi-scan (MULABS; Spek, 2003; Blessing, 1995) | 3571 reflections with I > 2σ(I) |
Tmin = 0.923, Tmax = 0.954 | Rint = 0.082 |
42568 measured reflections |
R[F2 > 2σ(F2)] = 0.079 | 0 restraints |
wR(F2) = 0.240 | H-atom parameters constrained |
S = 1.06 | Δρmax = 0.79 e Å−3 |
4478 reflections | Δρmin = −0.48 e Å−3 |
282 parameters |
Experimental. ; |
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 | 0.48440 (11) | 0.23608 (16) | 0.76976 (8) | 0.0341 (4) | |
O1 | 0.8050 (3) | 0.0042 (5) | 0.38379 (19) | 0.0334 (9) | |
N1 | 0.6287 (3) | 0.1143 (5) | 0.6373 (2) | 0.0310 (10) | |
N2 | 0.5907 (3) | 0.1107 (5) | 0.6946 (2) | 0.0297 (10) | |
H2 | 0.5967 | 0.0253 | 0.7215 | 0.036* | |
N3 | 0.5500 (3) | 0.3732 (5) | 0.6715 (2) | 0.0304 (10) | |
H3A | 0.5826 | 0.3733 | 0.6403 | 0.036* | |
H3B | 0.5206 | 0.4603 | 0.6789 | 0.036* | |
C1 | 0.6949 (4) | 0.0096 (6) | 0.6359 (3) | 0.0247 (10) | |
C2 | 0.7407 (4) | −0.1069 (8) | 0.6946 (3) | 0.0395 (13) | |
H2A | 0.7371 | −0.0650 | 0.7402 | 0.06 (2)* | |
H2B | 0.8095 | −0.1235 | 0.6977 | 0.07 (2)* | |
H2C | 0.7055 | −0.2082 | 0.6842 | 0.14 (5)* | |
C3 | 0.5450 (4) | 0.2403 (6) | 0.7077 (3) | 0.0266 (10) | |
C11 | 0.7240 (4) | 0.0096 (6) | 0.5701 (3) | 0.0258 (10) | |
C12 | 0.6569 (4) | 0.0578 (6) | 0.5050 (3) | 0.0274 (10) | |
H12 | 0.5933 | 0.0912 | 0.5041 | 0.033* | |
C13 | 0.6808 (4) | 0.0583 (6) | 0.4416 (3) | 0.0290 (11) | |
H13 | 0.6342 | 0.0910 | 0.3980 | 0.035* | |
C14 | 0.7742 (4) | 0.0099 (6) | 0.4433 (3) | 0.0277 (11) | |
C15 | 0.8419 (4) | −0.0382 (7) | 0.5070 (3) | 0.0302 (11) | |
H15 | 0.9055 | −0.0709 | 0.5077 | 0.036* | |
C16 | 0.8172 (4) | −0.0388 (7) | 0.5697 (3) | 0.0279 (11) | |
H16 | 0.8641 | −0.0724 | 0.6131 | 0.033* | |
C17 | 0.7387 (4) | 0.0625 (8) | 0.3175 (3) | 0.0409 (14) | |
H17A | 0.6813 | −0.0074 | 0.3019 | 0.061* | |
H17B | 0.7720 | 0.0642 | 0.2809 | 0.061* | |
H17C | 0.7176 | 0.1703 | 0.3246 | 0.061* | |
S1A | −0.04879 (11) | 0.28900 (16) | 0.75014 (8) | 0.0352 (4) | |
O1A | 0.3755 (3) | 0.4380 (5) | 0.42642 (19) | 0.0332 (9) | |
N1A | 0.1031 (3) | 0.4094 (5) | 0.6234 (2) | 0.0281 (9) | |
N2A | 0.0390 (3) | 0.4199 (5) | 0.6636 (2) | 0.0260 (9) | |
H2N | 0.0117 | 0.5106 | 0.6690 | 0.031* | |
N3A | 0.0556 (4) | 0.1494 (5) | 0.6767 (2) | 0.0339 (10) | |
H3A1 | 0.0897 | 0.1504 | 0.6464 | 0.041* | |
H3A2 | 0.0448 | 0.0590 | 0.6955 | 0.041* | |
C1A | 0.1091 (4) | 0.5312 (6) | 0.5826 (3) | 0.0264 (10) | |
C2A | 0.0463 (4) | 0.6765 (6) | 0.5725 (3) | 0.0310 (11) | |
H2A1 | −0.0167 | 0.6492 | 0.5790 | 0.07 (2)* | |
H2A2 | 0.0351 | 0.7183 | 0.5240 | 0.07 (2)* | |
H2A3 | 0.0794 | 0.7572 | 0.6076 | 0.11 (4)* | |
C3A | 0.0204 (4) | 0.2839 (6) | 0.6939 (2) | 0.0247 (10) | |
C11A | 0.1823 (4) | 0.5119 (6) | 0.5444 (3) | 0.0254 (10) | |
C12A | 0.2609 (4) | 0.4073 (6) | 0.5702 (3) | 0.0292 (11) | |
H12A | 0.2697 | 0.3540 | 0.6143 | 0.035* | |
C13A | 0.3268 (4) | 0.3796 (6) | 0.5323 (3) | 0.0294 (11) | |
H13A | 0.3799 | 0.3081 | 0.5505 | 0.035* | |
C14A | 0.3143 (4) | 0.4573 (6) | 0.4679 (3) | 0.0266 (10) | |
C15A | 0.2370 (4) | 0.5645 (7) | 0.4413 (3) | 0.0297 (11) | |
H15A | 0.2290 | 0.6181 | 0.3973 | 0.036* | |
C16A | 0.1721 (4) | 0.5919 (7) | 0.4799 (3) | 0.0296 (11) | |
H16A | 0.1201 | 0.6658 | 0.4623 | 0.036* | |
C17A | 0.4539 (4) | 0.3252 (6) | 0.4501 (3) | 0.0322 (12) | |
H17D | 0.4976 | 0.3570 | 0.4972 | 0.048* | |
H17E | 0.4909 | 0.3221 | 0.4158 | 0.048* | |
H17F | 0.4268 | 0.2197 | 0.4535 | 0.048* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0511 (8) | 0.0239 (6) | 0.0392 (7) | −0.0035 (6) | 0.0314 (6) | −0.0025 (5) |
O1 | 0.034 (2) | 0.041 (2) | 0.0301 (18) | 0.0052 (16) | 0.0170 (16) | 0.0016 (16) |
N1 | 0.039 (2) | 0.028 (2) | 0.032 (2) | −0.0009 (19) | 0.020 (2) | −0.0008 (18) |
N2 | 0.045 (3) | 0.022 (2) | 0.030 (2) | 0.0007 (19) | 0.023 (2) | 0.0026 (17) |
N3 | 0.043 (3) | 0.028 (2) | 0.027 (2) | 0.001 (2) | 0.022 (2) | −0.0018 (18) |
C1 | 0.023 (2) | 0.024 (2) | 0.027 (2) | −0.0009 (19) | 0.0091 (19) | 0.0019 (19) |
C2 | 0.042 (3) | 0.049 (3) | 0.029 (3) | 0.014 (3) | 0.012 (2) | 0.009 (3) |
C3 | 0.033 (3) | 0.024 (2) | 0.025 (2) | −0.006 (2) | 0.013 (2) | −0.0031 (19) |
C11 | 0.031 (3) | 0.019 (2) | 0.029 (2) | 0.0030 (19) | 0.012 (2) | 0.0005 (19) |
C12 | 0.025 (2) | 0.029 (3) | 0.029 (2) | 0.005 (2) | 0.010 (2) | 0.002 (2) |
C13 | 0.030 (3) | 0.030 (3) | 0.027 (2) | 0.004 (2) | 0.009 (2) | 0.002 (2) |
C14 | 0.034 (3) | 0.025 (3) | 0.029 (2) | 0.000 (2) | 0.016 (2) | 0.000 (2) |
C15 | 0.026 (3) | 0.033 (3) | 0.034 (3) | 0.002 (2) | 0.012 (2) | 0.000 (2) |
C16 | 0.023 (2) | 0.033 (3) | 0.027 (2) | 0.006 (2) | 0.007 (2) | 0.004 (2) |
C17 | 0.041 (3) | 0.055 (4) | 0.028 (3) | 0.005 (3) | 0.013 (2) | 0.007 (3) |
S1A | 0.0495 (8) | 0.0254 (6) | 0.0436 (8) | −0.0024 (6) | 0.0331 (7) | −0.0012 (5) |
O1A | 0.036 (2) | 0.037 (2) | 0.0314 (18) | 0.0035 (17) | 0.0180 (17) | 0.0046 (16) |
N1A | 0.033 (2) | 0.027 (2) | 0.030 (2) | 0.0015 (18) | 0.0175 (19) | 0.0035 (17) |
N2A | 0.035 (2) | 0.0195 (19) | 0.029 (2) | 0.0019 (17) | 0.0177 (19) | 0.0037 (16) |
N3A | 0.051 (3) | 0.023 (2) | 0.037 (2) | −0.005 (2) | 0.027 (2) | −0.0012 (19) |
C1A | 0.030 (3) | 0.024 (2) | 0.024 (2) | −0.001 (2) | 0.007 (2) | −0.0010 (19) |
C2A | 0.040 (3) | 0.025 (3) | 0.035 (3) | 0.005 (2) | 0.021 (2) | 0.003 (2) |
C3A | 0.029 (2) | 0.022 (2) | 0.024 (2) | −0.004 (2) | 0.010 (2) | −0.0012 (18) |
C11A | 0.030 (3) | 0.021 (2) | 0.026 (2) | −0.0071 (19) | 0.011 (2) | −0.0039 (18) |
C12A | 0.034 (3) | 0.030 (3) | 0.024 (2) | 0.000 (2) | 0.009 (2) | 0.004 (2) |
C13A | 0.031 (3) | 0.031 (3) | 0.030 (2) | 0.004 (2) | 0.014 (2) | 0.005 (2) |
C14A | 0.030 (3) | 0.024 (2) | 0.028 (2) | −0.003 (2) | 0.013 (2) | −0.003 (2) |
C15A | 0.030 (3) | 0.035 (3) | 0.026 (2) | −0.004 (2) | 0.012 (2) | 0.001 (2) |
C16A | 0.031 (3) | 0.030 (3) | 0.029 (3) | −0.002 (2) | 0.012 (2) | 0.000 (2) |
C17A | 0.032 (3) | 0.028 (3) | 0.040 (3) | 0.001 (2) | 0.016 (2) | −0.001 (2) |
S1—C3 | 1.704 (5) | S1A—C3A | 1.701 (5) |
O1—C14 | 1.374 (6) | O1A—C14A | 1.381 (6) |
O1—C17 | 1.439 (7) | O1A—C17A | 1.434 (6) |
N1—C1 | 1.302 (6) | N1A—C1A | 1.320 (7) |
N1—N2 | 1.398 (6) | N1A—N2A | 1.389 (6) |
N2—C3 | 1.338 (6) | N2A—C3A | 1.354 (6) |
N2—H2 | 0.8800 | N2A—H2N | 0.8800 |
N3—C3 | 1.339 (7) | N3A—C3A | 1.326 (7) |
N3—H3A | 0.8800 | N3A—H3A1 | 0.8800 |
N3—H3B | 0.8800 | N3A—H3A2 | 0.8800 |
C1—C11 | 1.478 (7) | C1A—C11A | 1.478 (7) |
C1—C2 | 1.500 (7) | C1A—C2A | 1.495 (7) |
C2—H2A | 0.9800 | C2A—H2A1 | 0.9800 |
C2—H2B | 0.9800 | C2A—H2A2 | 0.9800 |
C2—H2C | 0.9800 | C2A—H2A3 | 0.9800 |
C11—C12 | 1.401 (7) | C11A—C12A | 1.397 (7) |
C11—C16 | 1.401 (7) | C11A—C16A | 1.402 (7) |
C12—C13 | 1.391 (7) | C12A—C13A | 1.393 (7) |
C12—H12 | 0.9500 | C12A—H12A | 0.9500 |
C13—C14 | 1.391 (7) | C13A—C14A | 1.387 (7) |
C13—H13 | 0.9500 | C13A—H13A | 0.9500 |
C14—C15 | 1.386 (8) | C14A—C15A | 1.398 (8) |
C15—C16 | 1.384 (7) | C15A—C16A | 1.393 (7) |
C15—H15 | 0.9500 | C15A—H15A | 0.9500 |
C16—H16 | 0.9500 | C16A—H16A | 0.9500 |
C17—H17A | 0.9800 | C17A—H17D | 0.9800 |
C17—H17B | 0.9800 | C17A—H17E | 0.9800 |
C17—H17C | 0.9800 | C17A—H17F | 0.9800 |
C14—O1—C17 | 117.4 (4) | C14A—O1A—C17A | 117.7 (4) |
C1—N1—N2 | 118.2 (4) | C1A—N1A—N2A | 118.4 (4) |
C3—N2—N1 | 118.4 (4) | C3A—N2A—N1A | 116.9 (4) |
C3—N2—H2 | 120.8 | C3A—N2A—H2N | 121.6 |
N1—N2—H2 | 120.8 | N1A—N2A—H2N | 121.6 |
C3—N3—H3A | 120.0 | C3A—N3A—H3A1 | 120.0 |
C3—N3—H3B | 120.0 | C3A—N3A—H3A2 | 120.0 |
H3A—N3—H3B | 120.0 | H3A1—N3A—H3A2 | 120.0 |
N1—C1—C11 | 115.1 (4) | N1A—C1A—C11A | 114.5 (4) |
N1—C1—C2 | 125.1 (5) | N1A—C1A—C2A | 124.4 (5) |
C11—C1—C2 | 119.8 (4) | C11A—C1A—C2A | 121.1 (4) |
C1—C2—H2A | 109.5 | C1A—C2A—H2A1 | 109.5 |
C1—C2—H2B | 109.5 | C1A—C2A—H2A2 | 109.5 |
H2A—C2—H2B | 109.5 | H2A1—C2A—H2A2 | 109.5 |
C1—C2—H2C | 109.5 | C1A—C2A—H2A3 | 109.5 |
H2A—C2—H2C | 109.5 | H2A1—C2A—H2A3 | 109.5 |
H2B—C2—H2C | 109.5 | H2A2—C2A—H2A3 | 109.5 |
N2—C3—N3 | 117.9 (4) | N3A—C3A—N2A | 117.8 (4) |
N2—C3—S1 | 120.7 (4) | N3A—C3A—S1A | 122.2 (4) |
N3—C3—S1 | 121.4 (4) | N2A—C3A—S1A | 120.0 (4) |
C12—C11—C16 | 117.7 (5) | C12A—C11A—C16A | 118.4 (5) |
C12—C11—C1 | 119.9 (5) | C12A—C11A—C1A | 120.5 (4) |
C16—C11—C1 | 122.4 (5) | C16A—C11A—C1A | 121.1 (5) |
C13—C12—C11 | 121.9 (5) | C13A—C12A—C11A | 121.2 (5) |
C13—C12—H12 | 119.1 | C13A—C12A—H12A | 119.4 |
C11—C12—H12 | 119.1 | C11A—C12A—H12A | 119.4 |
C12—C13—C14 | 118.8 (5) | C14A—C13A—C12A | 119.5 (5) |
C12—C13—H13 | 120.6 | C14A—C13A—H13A | 120.2 |
C14—C13—H13 | 120.6 | C12A—C13A—H13A | 120.2 |
O1—C14—C15 | 116.0 (5) | O1A—C14A—C13A | 123.9 (5) |
O1—C14—C13 | 123.6 (5) | O1A—C14A—C15A | 115.6 (4) |
C15—C14—C13 | 120.4 (5) | C13A—C14A—C15A | 120.5 (5) |
C16—C15—C14 | 120.3 (5) | C16A—C15A—C14A | 119.4 (5) |
C16—C15—H15 | 119.9 | C16A—C15A—H15A | 120.3 |
C14—C15—H15 | 119.9 | C14A—C15A—H15A | 120.3 |
C15—C16—C11 | 120.9 (5) | C15A—C16A—C11A | 120.9 (5) |
C15—C16—H16 | 119.6 | C15A—C16A—H16A | 119.5 |
C11—C16—H16 | 119.6 | C11A—C16A—H16A | 119.5 |
O1—C17—H17A | 109.5 | O1A—C17A—H17D | 109.5 |
O1—C17—H17B | 109.5 | O1A—C17A—H17E | 109.5 |
H17A—C17—H17B | 109.5 | H17D—C17A—H17E | 109.5 |
O1—C17—H17C | 109.5 | O1A—C17A—H17F | 109.5 |
H17A—C17—H17C | 109.5 | H17D—C17A—H17F | 109.5 |
H17B—C17—H17C | 109.5 | H17E—C17A—H17F | 109.5 |
C1—N1—N2—C3 | 161.5 (5) | C1A—N1A—N2A—C3A | 167.8 (5) |
N2—N1—C1—C11 | 173.8 (4) | N2A—N1A—C1A—C11A | 177.5 (4) |
N2—N1—C1—C2 | −5.8 (8) | N2A—N1A—C1A—C2A | −4.4 (7) |
N1—N2—C3—N3 | −9.0 (7) | N1A—N2A—C3A—N3A | −7.4 (7) |
N1—N2—C3—S1 | 172.2 (4) | N1A—N2A—C3A—S1A | 174.4 (3) |
N1—C1—C11—C12 | −28.9 (7) | N1A—C1A—C11A—C12A | −23.1 (7) |
C2—C1—C11—C12 | 150.7 (5) | C2A—C1A—C11A—C12A | 158.7 (5) |
N1—C1—C11—C16 | 151.7 (5) | N1A—C1A—C11A—C16A | 153.8 (5) |
C2—C1—C11—C16 | −28.7 (8) | C2A—C1A—C11A—C16A | −24.3 (7) |
C16—C11—C12—C13 | 0.1 (8) | C16A—C11A—C12A—C13A | −1.4 (8) |
C1—C11—C12—C13 | −179.3 (5) | C1A—C11A—C12A—C13A | 175.6 (5) |
C11—C12—C13—C14 | −0.3 (8) | C11A—C12A—C13A—C14A | 0.0 (8) |
C17—O1—C14—C15 | −176.3 (5) | C17A—O1A—C14A—C13A | 2.9 (7) |
C17—O1—C14—C13 | 4.6 (8) | C17A—O1A—C14A—C15A | −177.9 (5) |
C12—C13—C14—O1 | 179.3 (5) | C12A—C13A—C14A—O1A | −180.0 (5) |
C12—C13—C14—C15 | 0.2 (8) | C12A—C13A—C14A—C15A | 0.9 (8) |
O1—C14—C15—C16 | −179.1 (5) | O1A—C14A—C15A—C16A | −179.7 (5) |
C13—C14—C15—C16 | 0.1 (8) | C13A—C14A—C15A—C16A | −0.5 (8) |
C14—C15—C16—C11 | −0.3 (8) | C14A—C15A—C16A—C11A | −0.9 (8) |
C12—C11—C16—C15 | 0.2 (8) | C12A—C11A—C16A—C15A | 1.8 (8) |
C1—C11—C16—C15 | 179.6 (5) | C1A—C11A—C16A—C15A | −175.2 (5) |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2···S1i | 0.88 | 2.73 | 3.472 (4) | 143 |
N3—H3A···O1Aii | 0.88 | 2.26 | 2.942 (5) | 135 |
N3—H3B···S1iii | 0.88 | 2.54 | 3.355 (5) | 154 |
N2A—H2N···S1Aiv | 0.88 | 2.79 | 3.521 (4) | 142 |
N3A—H3A1···O1v | 0.88 | 2.21 | 2.927 (6) | 138 |
N3A—H3A2···S1Avi | 0.88 | 2.50 | 3.370 (5) | 169 |
Symmetry codes: (i) −x+1, y−1/2, −z+3/2; (ii) −x+1, −y+1, −z+1; (iii) −x+1, y+1/2, −z+3/2; (iv) −x, y+1/2, −z+3/2; (v) −x+1, −y, −z+1; (vi) −x, y−1/2, −z+3/2. |
Experimental details
Crystal data | |
Chemical formula | C10H13N3OS |
Mr | 223.29 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 173 |
a, b, c (Å) | 14.3548 (9), 8.4141 (5), 19.6562 (13) |
β (°) | 108.123 (5) |
V (Å3) | 2256.4 (3) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.27 |
Crystal size (mm) | 0.31 × 0.25 × 0.18 |
Data collection | |
Diffractometer | Stoe IPDSII two-circle diffractometer |
Absorption correction | Multi-scan (MULABS; Spek, 2003; Blessing, 1995) |
Tmin, Tmax | 0.923, 0.954 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 42568, 4478, 3571 |
Rint | 0.082 |
(sin θ/λ)max (Å−1) | 0.623 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.079, 0.240, 1.06 |
No. of reflections | 4478 |
No. of parameters | 282 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.79, −0.48 |
Computer programs: X-AREA (Stoe & Cie, 2001), SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), XP in SHELXTL-Plus (Sheldrick, 1991).
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2···S1i | 0.88 | 2.73 | 3.472 (4) | 143.4 |
N3—H3A···O1Aii | 0.88 | 2.26 | 2.942 (5) | 134.6 |
N3—H3B···S1iii | 0.88 | 2.54 | 3.355 (5) | 154.3 |
N2A—H2N···S1Aiv | 0.88 | 2.79 | 3.521 (4) | 141.7 |
N3A—H3A1···O1v | 0.88 | 2.21 | 2.927 (6) | 138.2 |
N3A—H3A2···S1Avi | 0.88 | 2.50 | 3.370 (5) | 168.5 |
Symmetry codes: (i) −x+1, y−1/2, −z+3/2; (ii) −x+1, −y+1, −z+1; (iii) −x+1, y+1/2, −z+3/2; (iv) −x, y+1/2, −z+3/2; (v) −x+1, −y, −z+1; (vi) −x, y−1/2, −z+3/2. |
Thiourea and its derivatives have been the focus of attention in recent years in view of their interesting physicochemical properties and broad range of applications in several chemical disciplines. Certain thiourea molecules have antiviral activity and might be characterized as prospective inhibitors of many enzymes, particularly, HIV-1 reverse transcriptase (Ren et al., 2000; Onderwater et al., 2004). As antibacterial and antifungal agents, they have been used in agriculture (Rodriguez-Fernandez et al., 2005). In technical applications, dithioamide compounds are known to be prospective nonlinear optical materials (Zhou et al., 2003), corrosion inhibitors for copper and iron in acidic media (Stankovic & Vukovic 1996) and functionalization agents for production of chemically modified resins (Trochimczuk & Kolarz 2000). Thiourea derivatives have been also reported as potential receptors and ionophores for heavy metal cations (Castro et al., 2003), building blocks in the synthesis of heterocyclic compounds (Kearney et al., 1998). Finally, the strong hydrogen-bonding donor capability of the –N(H)—C(=S)—N(H)- group has been widely exploited in supramolecular chemistry, where it has been used as a building block for anion receptors (Nie et al., 2004). The crystal structures of 1-(2-bromo-5-methoxybenzoyl)thiosemicarbazide, (Sarojini et al., 2007), salicylaldehyde thiosemicarbazone (Chattopadhyay et al., 1988), 4-(methylsulfanyl)benzaldehyde thiosemicarbazone (Yathirajan et al., 2006) and benzoin thiosemicarbazone (Dinçer et al., 2005) A new carbothioamide, (I), C10H13N3OS, has been synthesized and its crystal structure is reported.
Geometric parameters of the title compound are in the usual ranges. There are two similar (r.m.s. deviation 0.131 Å for all non-H atoms) molecules in the asymmetric unit. The crystal packing is characterized by sheets in the (202) plane. The molecules in a sheet are connected by N—H···O and N—H···S hydrogen bonds.