Acta Cryst. (2009). E65, o2604-o2605 [ doi:10.1107/S1600536809036599 ]
The title compound, C17H19N3O3S, crystallizes with two closely similar independent molecules related by a pseudotranslation of c/2. Each molecule consists of three approximately planar moieties centred on the N2CS group and the two ring systems. The packing involves classical H bonds of the form Namide-H
S and Nhydrazine-HOC, together with various weak hydrogen bonds and Nhydrazine-H![[pi]](/logos/entities/pi_rmgif.gif)
interactions. The overall packing is three-dimensional, but layer substructures parallel to the xz plane can be readily identified. Each molecule forms a topologically equivalent set of hydrogen-bond interactions.
4-Ethoxybenzohydrazide (0.0068 moles) was dissolved in methanol (30 ml) and a solution of 4-methoxyphenylisothiocyanate (0.0066 moles), separately dissolved in 10 ml of methanol, was added dropwise with continuous stirring. The reaction mixture was refluxed for 10–12 h and progress of the reaction monitored by TLC. After consumption of the starting materials, the mixture was cooled to room temperature. The methanol was removed to give the crude thiosemicarbazide as an oil that solidified on cooling. The product was recrystallized from ethanol as large colourless blocks that were cut to size for X-ray analysis.
The NH H atoms were refined freely but with N—H distances restrained equal. Methyl H atoms were identified in difference syntheses, idealized and refined as rigid groups with C—H 0.98 Å and H—C—H angles 109.5°, allowed to rotate but not tip. Other H atoms were placed in calculated positions and refined using a riding model with C—Harom 0.95 and C—Hmethylene 0.99 Å; the hydrogen U values were fixed at 1.5 (methyl) or 1.2 × U(eq) of the parent carbon atom.
The compound is achiral but crystallizes by chance in a chiral space group. The translational pseudosymmetry causes the reflections with l odd to be weak, but they are definitely present.
Data collection: CrysAlis PRO (Oxford Diffraction, 2009); cell refinement: CrysAlis PRO (Oxford Diffraction, 2009); data reduction: CrysAlis PRO (Oxford Diffraction, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP (Siemens, 1994); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).
![[Figure 1]](./bt5057fig1thm.gif)
| Fig. 1. Molecular structure of the title compound showing the two independent molecules, the atom labelling scheme and displacement ellipsoids at the 50% probability level. |
![[Figure 2]](./bt5057fig2thm.gif)
| Fig. 2. A section of the three-dimensional packing diagram of the title compound viewed parallel to the x axis. Bond types: thick continuous bonds, molecule 1; open continuous bonds, molecule 2; thick dashed bonds, classical H bonds; thin dashed bonds, C—H···O interactions. For clarity, the ethoxy substituents and all H atoms not involved in the H bonds were omitted and the rings at N1 are shown only as their ipso carbons. |
| C17H19N3O3S | F(000) = 728 |
| Mr = 345.41 | Dx = 1.322 Mg m−3 |
| Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
| a = 15.40429 (13) Å | Cell parameters from 16506 reflections |
| b = 9.67120 (9) Å | θ = 2.3–30.7° |
| c = 11.69922 (9) Å | µ = 0.21 mm−1 |
| β = 95.0922 (7)° | T = 100 K |
| V = 1736.05 (3) Å3 | Tablet, colourless |
| Z = 4 | 0.3 × 0.2 × 0.1 mm |
| Oxford Diffraction Xcalibur E diffractometer | 9918 independent reflections |
| Radiation source: Enhance (Mo) X-ray Source | 6348 reflections with I > 2σ(I) |
| graphite | Rint = 0.032 |
| Detector resolution: 16.1419 pixels mm-1 | θmax = 30.5°, θmin = 2.3° |
| ω–scan | h = −21→21 |
| Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009) | k = −13→13 |
| Tmin = 0.981, Tmax = 1.000 | l = −15→16 |
| 44704 measured reflections |
| 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)] = 0.029 | H atoms treated by a mixture of independent and constrained refinement |
| wR(F2) = 0.055 | w = 1/[σ2(Fo2) + (0.020P)2] where P = (Fo2 + 2Fc2)/3 |
| S = 0.96 | (Δ/σ)max = 0.001 |
| 9918 reflections | Δρmax = 0.30 e Å−3 |
| 461 parameters | Δρmin = −0.23 e Å−3 |
| 16 restraints | Absolute structure: Flack (1983), 4562 Friedel pairs |
| Primary atom site location: structure-invariant direct methods | Flack parameter: 0.01 (3) |
| C17H19N3O3S | V = 1736.05 (3) Å3 |
| Mr = 345.41 | Z = 4 |
| Monoclinic, P21 | Mo Kα radiation |
| a = 15.40429 (13) Å | µ = 0.21 mm−1 |
| b = 9.67120 (9) Å | T = 100 K |
| c = 11.69922 (9) Å | 0.3 × 0.2 × 0.1 mm |
| β = 95.0922 (7)° |
| Oxford Diffraction Xcalibur E diffractometer | 9918 independent reflections |
| Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009) | 6348 reflections with I > 2σ(I) |
| Tmin = 0.981, Tmax = 1.000 | Rint = 0.032 |
| 44704 measured reflections | θmax = 30.5° |
| R[F2 > 2σ(F2)] = 0.029 | H atoms treated by a mixture of independent and constrained refinement |
| wR(F2) = 0.055 | Δρmax = 0.30 e Å−3 |
| S = 0.96 | Δρmin = −0.23 e Å−3 |
| 9918 reflections | Absolute structure: Flack (1983), 4562 Friedel pairs |
| 461 parameters | Flack parameter: 0.01 (3) |
| 16 restraints |
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. Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane) 13.0283 (0.0011) x + 1.4133 (0.0037) y - 6.8581 (0.0016) z = 2.4289 (0.0026) * 0.0169 (0.0013) C6 * 0.0162 (0.0012) C7 * 0.0312 (0.0012) C8 * 0.0483 (0.0013) C9 * 0.0676 (0.0014) C10 * 0.0481 (0.0013) C11 * 0.0436 (0.0010) O2 * -0.0206 (0.0014) C12 * -0.1392 (0.0013) C13 * 0.0011 (0.0013) C5 * -0.0780 (0.0010) O1 * 0.0952 (0.0010) N4 * -0.1306 (0.0010) N3 Rms deviation of fitted atoms = 0.0705 - 5.8835 (0.0067) x + 8.3025 (0.0025) y + 4.3848 (0.0043) z = 4.5767 (0.0054) Angle to previous plane (with approximate e.s.d.) = 68.09 (0.03) * -0.0909 (0.0013) N1 * -0.0296 (0.0012) C2 * 0.0247 (0.0006) S * 0.0499 (0.0008) N4 * -0.0143 (0.0011) N3 * 0.0602 (0.0008) C14 Rms deviation of fitted atoms = 0.0518 4.4124 (0.0064) x - 7.2670 (0.0036) y + 6.6294 (0.0075) z = 4.1549 (0.0063) Angle to previous plane (with approximate e.s.d.) = 56.56 (0.04) * 0.0131 (0.0015) C14 * 0.0077 (0.0017) C15 * -0.0154 (0.0018) C16 * 0.0007 (0.0017) C17 * -0.0065 (0.0015) C18 * -0.0105 (0.0015) C19 * -0.0002 (0.0013) O3 * 0.0099 (0.0013) C20 * 0.0012 (0.0012) N1 Rms deviation of fitted atoms = 0.0089 13.0659 (0.0012) x + 1.8489 (0.0037) y - 6.6371 (0.0017) z = 6.1077 (0.0017) Angle to previous plane (with approximate e.s.d.) = 78.79 (0.03) * 0.0172 (0.0013) C6' * 0.0319 (0.0011) C7' * 0.0585 (0.0011) C8' * 0.0569 (0.0013) C9' * 0.0548 (0.0014) C10' * 0.0249 (0.0013) C11' * 0.0496 (0.0010) O2' * -0.0083 (0.0015) C12' * -0.1597 (0.0014) C13' * -0.0114 (0.0013) C5' * -0.1233 (0.0010) O1' * 0.1239 (0.0010) N4' * -0.1150 (0.0010) N3' Rms deviation of fitted atoms = 0.0802 - 4.7715 (0.0070) x + 8.8203 (0.0020) y + 3.4544 (0.0044) z = 2.9970 (0.0051) Angle to previous plane (with approximate e.s.d.) = 77.22 (0.03) * -0.0881 (0.0013) N1' * -0.0271 (0.0012) C2' * 0.0344 (0.0006) S' * 0.0675 (0.0008) N4' * -0.0418 (0.0011) N3' * 0.0550 (0.0008) C14' Rms deviation of fitted atoms = 0.0563 2.1176 (0.0060) x - 6.0315 (0.0044) y + 8.8245 (0.0052) z = 0.7518 (0.0041) Angle to previous plane (with approximate e.s.d.) = 66.14 (0.03) * 0.0140 (0.0014) C14' * 0.0048 (0.0014) C15' * -0.0082 (0.0014) C16' * -0.0043 (0.0016) C17' * -0.0002 (0.0015) C18' * -0.0089 (0.0014) C19' * -0.0003 (0.0013) O3' * 0.0060 (0.0013) C20' * -0.0029 (0.0012) N1' Rms deviation of fitted atoms = 0.0069 |
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 | ||
| S | 0.70206 (2) | 0.50456 (5) | 1.03604 (3) | 0.01728 (10) | |
| O1 | 0.52373 (7) | 0.30901 (11) | 0.71581 (8) | 0.0180 (2) | |
| O2 | 0.28479 (6) | 0.55263 (11) | 0.29437 (8) | 0.0211 (3) | |
| O3 | 1.02907 (7) | 0.86352 (16) | 0.88836 (10) | 0.0411 (4) | |
| N1 | 0.70429 (8) | 0.60538 (15) | 0.82176 (11) | 0.0181 (3) | |
| H01 | 0.6823 (9) | 0.6052 (17) | 0.7547 (10) | 0.021 (5)* | |
| C2 | 0.66134 (9) | 0.54043 (16) | 0.90110 (11) | 0.0125 (3) | |
| N3 | 0.57906 (8) | 0.50134 (15) | 0.86822 (10) | 0.0142 (3) | |
| H03 | 0.5512 (8) | 0.4637 (14) | 0.9164 (10) | 0.005 (4)* | |
| N4 | 0.53669 (8) | 0.53524 (14) | 0.76180 (10) | 0.0133 (3) | |
| H04 | 0.5143 (10) | 0.6113 (14) | 0.7606 (14) | 0.027 (6)* | |
| C5 | 0.50445 (9) | 0.42990 (16) | 0.69256 (13) | 0.0128 (3) | |
| C6 | 0.44704 (9) | 0.47015 (16) | 0.58951 (12) | 0.0122 (3) | |
| C7 | 0.41778 (9) | 0.36550 (16) | 0.51243 (12) | 0.0148 (4) | |
| H7 | 0.4349 | 0.2724 | 0.5274 | 0.018* | |
| C8 | 0.36421 (10) | 0.39690 (17) | 0.41495 (12) | 0.0169 (4) | |
| H8 | 0.3447 | 0.3252 | 0.3634 | 0.020* | |
| C9 | 0.33859 (9) | 0.53260 (17) | 0.39175 (12) | 0.0157 (3) | |
| C10 | 0.36805 (10) | 0.63793 (17) | 0.46663 (12) | 0.0171 (4) | |
| H10 | 0.3516 | 0.7311 | 0.4507 | 0.021* | |
| C11 | 0.42156 (10) | 0.60574 (16) | 0.56447 (13) | 0.0157 (4) | |
| H11 | 0.4413 | 0.6777 | 0.6156 | 0.019* | |
| C12 | 0.25273 (10) | 0.69102 (17) | 0.27136 (13) | 0.0244 (4) | |
| H12A | 0.3015 | 0.7539 | 0.2577 | 0.029* | |
| H12B | 0.2234 | 0.7264 | 0.3374 | 0.029* | |
| C13 | 0.18893 (11) | 0.68298 (19) | 0.16578 (13) | 0.0312 (5) | |
| H13A | 0.2177 | 0.6421 | 0.1025 | 0.047* | |
| H13B | 0.1685 | 0.7762 | 0.1443 | 0.047* | |
| H13C | 0.1391 | 0.6255 | 0.1821 | 0.047* | |
| C14 | 0.78727 (10) | 0.67202 (18) | 0.84138 (13) | 0.0198 (4) | |
| C15 | 0.85155 (11) | 0.6460 (2) | 0.76923 (14) | 0.0428 (6) | |
| H15 | 0.8414 | 0.5821 | 0.7078 | 0.051* | |
| C16 | 0.93107 (12) | 0.7134 (3) | 0.78670 (14) | 0.0503 (7) | |
| H16 | 0.9746 | 0.6970 | 0.7357 | 0.060* | |
| C17 | 0.94779 (10) | 0.8035 (2) | 0.87684 (14) | 0.0298 (5) | |
| C18 | 0.88347 (10) | 0.83019 (18) | 0.94777 (15) | 0.0270 (4) | |
| H18 | 0.8938 | 0.8933 | 1.0097 | 0.032* | |
| C19 | 0.80302 (10) | 0.76466 (18) | 0.92888 (15) | 0.0272 (4) | |
| H19 | 0.7584 | 0.7846 | 0.9775 | 0.033* | |
| C20 | 1.04658 (11) | 0.9572 (2) | 0.98097 (15) | 0.0376 (5) | |
| H20A | 1.0051 | 1.0342 | 0.9729 | 0.056* | |
| H20B | 1.1061 | 0.9930 | 0.9803 | 0.056* | |
| H20C | 1.0406 | 0.9092 | 1.0536 | 0.056* | |
| S' | 0.69682 (2) | 0.51034 (4) | 0.53698 (3) | 0.01624 (9) | |
| O1' | 0.52337 (7) | 0.30780 (11) | 0.21440 (8) | 0.0184 (2) | |
| O2' | 0.28670 (6) | 0.54492 (11) | −0.21151 (8) | 0.0215 (3) | |
| O3' | 1.04034 (7) | 0.80274 (17) | 0.38417 (11) | 0.0439 (4) | |
| N1' | 0.70424 (8) | 0.58667 (14) | 0.31685 (11) | 0.0161 (3) | |
| H01' | 0.6834 (9) | 0.5828 (16) | 0.2504 (10) | 0.017 (5)* | |
| C2' | 0.65809 (9) | 0.53631 (15) | 0.39935 (11) | 0.0122 (3) | |
| N3' | 0.57447 (7) | 0.50178 (15) | 0.36778 (10) | 0.0139 (3) | |
| H03' | 0.5419 (8) | 0.4738 (15) | 0.4176 (10) | 0.012 (4)* | |
| N4' | 0.53359 (8) | 0.53414 (14) | 0.26033 (10) | 0.0133 (3) | |
| H04' | 0.5104 (10) | 0.6123 (14) | 0.2551 (13) | 0.023 (5)* | |
| C5' | 0.50319 (9) | 0.42750 (16) | 0.19115 (12) | 0.0130 (3) | |
| C6' | 0.44667 (9) | 0.46655 (16) | 0.08647 (12) | 0.0118 (3) | |
| C7' | 0.42218 (9) | 0.36192 (16) | 0.00689 (12) | 0.0140 (3) | |
| H7' | 0.4418 | 0.2699 | 0.0212 | 0.017* | |
| C8' | 0.36966 (9) | 0.39163 (17) | −0.09224 (12) | 0.0152 (3) | |
| H8' | 0.3539 | 0.3203 | −0.1460 | 0.018* | |
| C9' | 0.33984 (9) | 0.52599 (17) | −0.11327 (12) | 0.0157 (3) | |
| C10' | 0.36423 (10) | 0.63083 (17) | −0.03574 (13) | 0.0173 (4) | |
| H10' | 0.3450 | 0.7229 | −0.0508 | 0.021* | |
| C11' | 0.41673 (10) | 0.60055 (16) | 0.06368 (13) | 0.0155 (4) | |
| H11' | 0.4325 | 0.6723 | 0.1170 | 0.019* | |
| C12' | 0.25161 (11) | 0.68144 (18) | −0.23382 (14) | 0.0274 (4) | |
| H12C | 0.2990 | 0.7471 | −0.2472 | 0.033* | |
| H12D | 0.2217 | 0.7144 | −0.1675 | 0.033* | |
| C13' | 0.18795 (12) | 0.6718 (2) | −0.33901 (14) | 0.0392 (5) | |
| H13D | 0.2167 | 0.6298 | −0.4019 | 0.059* | |
| H13E | 0.1676 | 0.7647 | −0.3616 | 0.059* | |
| H13F | 0.1381 | 0.6147 | −0.3220 | 0.059* | |
| C14' | 0.79061 (10) | 0.64214 (18) | 0.33595 (13) | 0.0187 (4) | |
| C15' | 0.85761 (10) | 0.5858 (2) | 0.28031 (13) | 0.0280 (4) | |
| H15' | 0.8472 | 0.5088 | 0.2305 | 0.034* | |
| C16' | 0.94058 (10) | 0.6430 (2) | 0.29804 (13) | 0.0350 (5) | |
| H16' | 0.9869 | 0.6051 | 0.2597 | 0.042* | |
| C17' | 0.95622 (10) | 0.7544 (2) | 0.37088 (14) | 0.0294 (5) | |
| C18' | 0.88890 (10) | 0.81103 (19) | 0.42619 (15) | 0.0282 (4) | |
| H18' | 0.8994 | 0.8873 | 0.4767 | 0.034* | |
| C19' | 0.80553 (10) | 0.75494 (18) | 0.40688 (14) | 0.0259 (4) | |
| H19' | 0.7586 | 0.7948 | 0.4429 | 0.031* | |
| C20' | 1.05700 (12) | 0.9175 (2) | 0.45930 (16) | 0.0441 (6) | |
| H20D | 1.0241 | 0.9980 | 0.4285 | 0.066* | |
| H20E | 1.1194 | 0.9387 | 0.4658 | 0.066* | |
| H20F | 1.0389 | 0.8946 | 0.5352 | 0.066* |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| S | 0.0191 (2) | 0.0208 (3) | 0.01124 (19) | −0.0005 (2) | −0.00234 (16) | 0.00053 (18) |
| O1 | 0.0241 (6) | 0.0118 (6) | 0.0177 (6) | 0.0013 (5) | −0.0002 (5) | 0.0031 (5) |
| O2 | 0.0243 (6) | 0.0218 (7) | 0.0157 (6) | 0.0006 (5) | −0.0066 (5) | 0.0002 (5) |
| O3 | 0.0235 (7) | 0.0669 (11) | 0.0330 (7) | −0.0240 (7) | 0.0037 (6) | −0.0058 (7) |
| N1 | 0.0150 (7) | 0.0272 (9) | 0.0117 (7) | −0.0055 (6) | −0.0012 (6) | 0.0051 (6) |
| C2 | 0.0115 (7) | 0.0120 (9) | 0.0140 (8) | 0.0012 (6) | 0.0010 (6) | −0.0018 (6) |
| N3 | 0.0154 (6) | 0.0180 (8) | 0.0092 (7) | −0.0034 (6) | 0.0009 (5) | 0.0031 (6) |
| N4 | 0.0148 (7) | 0.0116 (8) | 0.0127 (7) | 0.0000 (6) | −0.0026 (5) | 0.0001 (6) |
| C5 | 0.0123 (8) | 0.0125 (9) | 0.0143 (8) | −0.0011 (7) | 0.0043 (6) | 0.0009 (7) |
| C6 | 0.0129 (8) | 0.0110 (9) | 0.0131 (8) | −0.0026 (6) | 0.0023 (6) | −0.0001 (6) |
| C7 | 0.0164 (8) | 0.0111 (9) | 0.0172 (9) | −0.0009 (7) | 0.0039 (7) | 0.0010 (7) |
| C8 | 0.0177 (8) | 0.0182 (10) | 0.0144 (8) | −0.0043 (7) | −0.0002 (7) | −0.0049 (7) |
| C9 | 0.0121 (7) | 0.0210 (10) | 0.0138 (8) | −0.0019 (7) | 0.0004 (6) | 0.0034 (7) |
| C10 | 0.0221 (8) | 0.0117 (9) | 0.0170 (9) | 0.0005 (7) | −0.0009 (7) | −0.0008 (7) |
| C11 | 0.0174 (8) | 0.0131 (10) | 0.0161 (9) | −0.0017 (7) | −0.0016 (7) | −0.0051 (7) |
| C12 | 0.0244 (10) | 0.0245 (11) | 0.0233 (10) | 0.0044 (8) | −0.0041 (8) | 0.0023 (8) |
| C13 | 0.0273 (10) | 0.0399 (12) | 0.0246 (10) | 0.0040 (8) | −0.0076 (8) | 0.0047 (8) |
| C14 | 0.0119 (8) | 0.0278 (10) | 0.0194 (9) | −0.0038 (7) | −0.0005 (6) | 0.0082 (7) |
| C15 | 0.0288 (10) | 0.0805 (18) | 0.0202 (9) | −0.0255 (11) | 0.0082 (7) | −0.0192 (10) |
| C16 | 0.0298 (11) | 0.096 (2) | 0.0274 (10) | −0.0292 (11) | 0.0170 (8) | −0.0178 (11) |
| C17 | 0.0194 (9) | 0.0454 (13) | 0.0240 (9) | −0.0128 (8) | −0.0023 (7) | 0.0086 (8) |
| C18 | 0.0211 (9) | 0.0215 (10) | 0.0387 (10) | −0.0053 (7) | 0.0048 (8) | −0.0080 (8) |
| C19 | 0.0180 (9) | 0.0214 (10) | 0.0434 (10) | −0.0038 (7) | 0.0087 (8) | −0.0077 (8) |
| C20 | 0.0245 (9) | 0.0496 (13) | 0.0374 (10) | −0.0197 (9) | −0.0049 (8) | 0.0030 (9) |
| S' | 0.0178 (2) | 0.0181 (2) | 0.01218 (19) | 0.0001 (2) | −0.00225 (15) | −0.00011 (18) |
| O1' | 0.0255 (6) | 0.0116 (7) | 0.0178 (6) | 0.0013 (5) | −0.0007 (5) | 0.0025 (5) |
| O2' | 0.0246 (6) | 0.0232 (7) | 0.0151 (6) | −0.0011 (5) | −0.0079 (5) | −0.0006 (5) |
| O3' | 0.0182 (6) | 0.0690 (11) | 0.0448 (8) | −0.0180 (7) | 0.0041 (6) | −0.0062 (7) |
| N1' | 0.0131 (7) | 0.0236 (8) | 0.0113 (7) | −0.0032 (6) | −0.0004 (6) | 0.0006 (6) |
| C2' | 0.0149 (8) | 0.0081 (9) | 0.0139 (8) | 0.0017 (6) | 0.0026 (6) | −0.0011 (6) |
| N3' | 0.0121 (6) | 0.0188 (8) | 0.0105 (7) | −0.0020 (6) | −0.0004 (5) | 0.0015 (6) |
| N4' | 0.0139 (7) | 0.0130 (9) | 0.0124 (7) | 0.0014 (6) | −0.0019 (5) | 0.0020 (6) |
| C5' | 0.0128 (8) | 0.0138 (9) | 0.0131 (8) | −0.0018 (7) | 0.0042 (6) | 0.0003 (7) |
| C6' | 0.0096 (7) | 0.0125 (9) | 0.0134 (8) | −0.0018 (6) | 0.0019 (6) | 0.0016 (7) |
| C7' | 0.0154 (8) | 0.0114 (9) | 0.0156 (8) | −0.0026 (7) | 0.0037 (7) | −0.0018 (7) |
| C8' | 0.0155 (8) | 0.0156 (9) | 0.0148 (8) | −0.0047 (7) | 0.0031 (6) | −0.0026 (7) |
| C9' | 0.0130 (7) | 0.0238 (10) | 0.0103 (7) | −0.0012 (7) | 0.0006 (6) | 0.0009 (7) |
| C10' | 0.0180 (8) | 0.0158 (9) | 0.0178 (9) | 0.0039 (7) | −0.0008 (7) | 0.0037 (7) |
| C11' | 0.0185 (8) | 0.0131 (9) | 0.0149 (9) | −0.0012 (7) | 0.0008 (7) | −0.0017 (7) |
| C12' | 0.0286 (10) | 0.0264 (11) | 0.0255 (10) | 0.0024 (8) | −0.0079 (8) | 0.0030 (8) |
| C13' | 0.0399 (12) | 0.0448 (14) | 0.0299 (11) | 0.0070 (10) | −0.0142 (9) | 0.0026 (9) |
| C14' | 0.0142 (8) | 0.0253 (10) | 0.0165 (8) | −0.0027 (7) | 0.0009 (6) | 0.0047 (7) |
| C15' | 0.0187 (8) | 0.0423 (12) | 0.0233 (9) | −0.0025 (8) | 0.0040 (7) | −0.0088 (8) |
| C16' | 0.0164 (9) | 0.0614 (14) | 0.0277 (10) | −0.0018 (9) | 0.0056 (7) | −0.0101 (9) |
| C17' | 0.0150 (8) | 0.0459 (13) | 0.0266 (9) | −0.0101 (8) | −0.0013 (7) | 0.0057 (9) |
| C18' | 0.0212 (9) | 0.0248 (10) | 0.0384 (10) | −0.0065 (8) | 0.0009 (8) | −0.0009 (8) |
| C19' | 0.0145 (8) | 0.0262 (11) | 0.0377 (10) | −0.0007 (7) | 0.0060 (7) | −0.0030 (8) |
| C20' | 0.0260 (10) | 0.0522 (14) | 0.0521 (13) | −0.0214 (10) | −0.0083 (9) | 0.0102 (10) |
| S—C2 | 1.6823 (14) | C14'—C19' | 1.378 (2) |
| O1—C5 | 1.2307 (17) | C14'—C15' | 1.380 (2) |
| O2—C9 | 1.3618 (16) | C15'—C16' | 1.391 (2) |
| O2—C12 | 1.4436 (18) | C16'—C17' | 1.382 (2) |
| O3—C17 | 1.3757 (18) | C17'—C18' | 1.383 (2) |
| O3—C20 | 1.420 (2) | C18'—C19' | 1.394 (2) |
| N1—C2 | 1.3428 (18) | N1—H01 | 0.826 (11) |
| N1—C14 | 1.4316 (19) | N3—H03 | 0.822 (10) |
| C2—N3 | 1.3457 (17) | N4—H04 | 0.812 (12) |
| N3—N4 | 1.3926 (16) | C7—H7 | 0.9500 |
| N4—C5 | 1.3672 (19) | C8—H8 | 0.9500 |
| C5—C6 | 1.482 (2) | C10—H10 | 0.9500 |
| C6—C11 | 1.393 (2) | C11—H11 | 0.9500 |
| C6—C7 | 1.4030 (19) | C12—H12A | 0.9900 |
| C7—C8 | 1.3809 (19) | C12—H12B | 0.9900 |
| C8—C9 | 1.390 (2) | C13—H13A | 0.9800 |
| C9—C10 | 1.393 (2) | C13—H13B | 0.9800 |
| C10—C11 | 1.3853 (19) | C13—H13C | 0.9800 |
| C12—C13 | 1.5108 (19) | C15—H15 | 0.9500 |
| C14—C19 | 1.366 (2) | C16—H16 | 0.9500 |
| C14—C15 | 1.380 (2) | C18—H18 | 0.9500 |
| C15—C16 | 1.387 (2) | C19—H19 | 0.9500 |
| C16—C17 | 1.375 (3) | C20—H20A | 0.9800 |
| C17—C18 | 1.372 (2) | C20—H20B | 0.9800 |
| C18—C19 | 1.392 (2) | C20—H20C | 0.9800 |
| S'—C2' | 1.6856 (14) | N1'—H01' | 0.816 (11) |
| O1'—C5' | 1.2229 (17) | N3'—H03' | 0.847 (10) |
| O2'—C9' | 1.3630 (16) | N4'—H04' | 0.836 (12) |
| O2'—C12' | 1.4417 (19) | C7'—H7' | 0.9500 |
| O3'—C17' | 1.3733 (18) | C8'—H8' | 0.9500 |
| O3'—C20' | 1.425 (2) | C10'—H10' | 0.9500 |
| N1'—C2' | 1.3402 (17) | C11'—H11' | 0.9500 |
| N1'—C14' | 1.4335 (19) | C12'—H12C | 0.9900 |
| C2'—N3' | 1.3501 (17) | C12'—H12D | 0.9900 |
| N3'—N4' | 1.3908 (16) | C13'—H13D | 0.9800 |
| N4'—C5' | 1.3678 (19) | C13'—H13E | 0.9800 |
| C5'—C6' | 1.487 (2) | C13'—H13F | 0.9800 |
| C6'—C11' | 1.393 (2) | C15'—H15' | 0.9500 |
| C6'—C7' | 1.4039 (19) | C16'—H16' | 0.9500 |
| C7'—C8' | 1.3840 (19) | C18'—H18' | 0.9500 |
| C8'—C9' | 1.393 (2) | C19'—H19' | 0.9500 |
| C9'—C10' | 1.390 (2) | C20'—H20D | 0.9800 |
| C10'—C11' | 1.3877 (19) | C20'—H20E | 0.9800 |
| C12'—C13' | 1.507 (2) | C20'—H20F | 0.9800 |
| C9—O2—C12 | 117.42 (12) | C6—C7—H7 | 119.8 |
| C17—O3—C20 | 116.97 (14) | C7—C8—H8 | 119.8 |
| C2—N1—C14 | 125.98 (13) | C9—C8—H8 | 119.8 |
| N1—C2—N3 | 116.31 (13) | C11—C10—H10 | 120.3 |
| N1—C2—S | 125.42 (11) | C9—C10—H10 | 120.3 |
| N3—C2—S | 118.27 (11) | C10—C11—H11 | 119.3 |
| C2—N3—N4 | 122.97 (12) | C6—C11—H11 | 119.3 |
| C5—N4—N3 | 118.10 (13) | O2—C12—H12A | 110.3 |
| O1—C5—N4 | 120.60 (15) | C13—C12—H12A | 110.3 |
| O1—C5—C6 | 122.96 (14) | O2—C12—H12B | 110.3 |
| N4—C5—C6 | 116.44 (14) | C13—C12—H12B | 110.3 |
| C11—C6—C7 | 118.40 (14) | H12A—C12—H12B | 108.6 |
| C11—C6—C5 | 123.71 (13) | C12—C13—H13A | 109.5 |
| C7—C6—C5 | 117.89 (14) | C12—C13—H13B | 109.5 |
| C8—C7—C6 | 120.43 (15) | H13A—C13—H13B | 109.5 |
| C7—C8—C9 | 120.49 (15) | C12—C13—H13C | 109.5 |
| O2—C9—C8 | 116.02 (14) | H13A—C13—H13C | 109.5 |
| O2—C9—C10 | 124.21 (15) | H13B—C13—H13C | 109.5 |
| C8—C9—C10 | 119.77 (14) | C14—C15—H15 | 120.1 |
| C11—C10—C9 | 119.48 (15) | C16—C15—H15 | 120.1 |
| C10—C11—C6 | 121.42 (14) | C17—C16—H16 | 119.5 |
| O2—C12—C13 | 106.96 (13) | C15—C16—H16 | 119.5 |
| C19—C14—C15 | 119.26 (15) | C17—C18—H18 | 120.0 |
| C19—C14—N1 | 120.81 (15) | C19—C18—H18 | 120.0 |
| C15—C14—N1 | 119.90 (15) | C14—C19—H19 | 119.5 |
| C14—C15—C16 | 119.76 (17) | C18—C19—H19 | 119.5 |
| C17—C16—C15 | 120.94 (17) | O3—C20—H20A | 109.5 |
| C18—C17—C16 | 119.13 (16) | O3—C20—H20B | 109.5 |
| C18—C17—O3 | 124.15 (16) | H20A—C20—H20B | 109.5 |
| C16—C17—O3 | 116.71 (16) | O3—C20—H20C | 109.5 |
| C17—C18—C19 | 119.93 (16) | H20A—C20—H20C | 109.5 |
| C14—C19—C18 | 120.94 (16) | H20B—C20—H20C | 109.5 |
| C9'—O2'—C12' | 117.59 (12) | C2'—N1'—H01' | 118.7 (11) |
| C17'—O3'—C20' | 116.84 (14) | C14'—N1'—H01' | 116.6 (11) |
| C2'—N1'—C14' | 124.62 (13) | C2'—N3'—H03' | 120.0 (9) |
| N1'—C2'—N3' | 116.56 (13) | N4'—N3'—H03' | 116.5 (9) |
| N1'—C2'—S' | 125.22 (11) | C5'—N4'—H04' | 121.1 (11) |
| N3'—C2'—S' | 118.21 (11) | N3'—N4'—H04' | 115.2 (11) |
| C2'—N3'—N4' | 122.41 (12) | C8'—C7'—H7' | 119.7 |
| C5'—N4'—N3' | 117.96 (13) | C6'—C7'—H7' | 119.7 |
| O1'—C5'—N4' | 121.01 (15) | C7'—C8'—H8' | 120.0 |
| O1'—C5'—C6' | 122.84 (14) | C9'—C8'—H8' | 120.0 |
| N4'—C5'—C6' | 116.14 (14) | C11'—C10'—H10' | 120.1 |
| C11'—C6'—C7' | 118.59 (14) | C9'—C10'—H10' | 120.1 |
| C11'—C6'—C5' | 123.61 (14) | C10'—C11'—H11' | 119.5 |
| C7'—C6'—C5' | 117.80 (14) | C6'—C11'—H11' | 119.5 |
| C8'—C7'—C6' | 120.58 (15) | O2'—C12'—H12C | 110.3 |
| C7'—C8'—C9' | 120.05 (14) | C13'—C12'—H12C | 110.3 |
| O2'—C9'—C10' | 124.03 (15) | O2'—C12'—H12D | 110.3 |
| O2'—C9'—C8' | 115.99 (14) | C13'—C12'—H12D | 110.3 |
| C10'—C9'—C8' | 119.97 (14) | H12C—C12'—H12D | 108.5 |
| C11'—C10'—C9' | 119.79 (15) | C12'—C13'—H13D | 109.5 |
| C10'—C11'—C6' | 121.00 (15) | C12'—C13'—H13E | 109.5 |
| O2'—C12'—C13' | 107.32 (14) | H13D—C13'—H13E | 109.5 |
| C19'—C14'—C15' | 120.33 (15) | C12'—C13'—H13F | 109.5 |
| C19'—C14'—N1' | 119.55 (15) | H13D—C13'—H13F | 109.5 |
| C15'—C14'—N1' | 120.08 (15) | H13E—C13'—H13F | 109.5 |
| C14'—C15'—C16' | 119.21 (17) | C14'—C15'—H15' | 120.4 |
| C17'—C16'—C15' | 120.65 (16) | C16'—C15'—H15' | 120.4 |
| O3'—C17'—C16' | 116.52 (16) | C17'—C16'—H16' | 119.7 |
| O3'—C17'—C18' | 123.46 (17) | C15'—C16'—H16' | 119.7 |
| C16'—C17'—C18' | 120.02 (16) | C17'—C18'—H18' | 120.4 |
| C17'—C18'—C19' | 119.23 (17) | C19'—C18'—H18' | 120.4 |
| C14'—C19'—C18' | 120.52 (16) | C14'—C19'—H19' | 119.7 |
| C2—N1—H01 | 118.0 (11) | C18'—C19'—H19' | 119.7 |
| C14—N1—H01 | 116.0 (11) | O3'—C20'—H20D | 109.5 |
| C2—N3—H03 | 117.6 (9) | O3'—C20'—H20E | 109.5 |
| N4—N3—H03 | 119.0 (9) | H20D—C20'—H20E | 109.5 |
| C5—N4—H04 | 122.2 (12) | O3'—C20'—H20F | 109.5 |
| N3—N4—H04 | 113.2 (12) | H20D—C20'—H20F | 109.5 |
| C8—C7—H7 | 119.8 | H20E—C20'—H20F | 109.5 |
| C14—N1—C2—N3 | 171.14 (15) | C14'—N1'—C2'—N3' | 173.21 (15) |
| C14—N1—C2—S | −9.0 (2) | C14'—N1'—C2'—S' | −8.1 (2) |
| N1—C2—N3—N4 | −5.3 (2) | N1'—C2'—N3'—N4' | −9.0 (2) |
| S—C2—N3—N4 | 174.82 (11) | S'—C2'—N3'—N4' | 172.22 (11) |
| C2—N3—N4—C5 | 123.25 (16) | C2'—N3'—N4'—C5' | 119.34 (16) |
| N3—N4—C5—O1 | −10.8 (2) | N3'—N4'—C5'—O1' | −11.7 (2) |
| N3—N4—C5—C6 | 169.88 (12) | N3'—N4'—C5'—C6' | 169.66 (11) |
| O1—C5—C6—C11 | 177.14 (15) | O1'—C5'—C6'—C11' | 174.11 (15) |
| N4—C5—C6—C11 | −3.6 (2) | N4'—C5'—C6'—C11' | −7.2 (2) |
| O1—C5—C6—C7 | −3.6 (2) | O1'—C5'—C6'—C7' | −5.6 (2) |
| N4—C5—C6—C7 | 175.64 (13) | N4'—C5'—C6'—C7' | 173.03 (13) |
| C11—C6—C7—C8 | −0.7 (2) | C11'—C6'—C7'—C8' | 0.2 (2) |
| C5—C6—C7—C8 | −179.97 (13) | C5'—C6'—C7'—C8' | 180.00 (13) |
| C6—C7—C8—C9 | 0.1 (2) | C6'—C7'—C8'—C9' | −0.7 (2) |
| C12—O2—C9—C8 | 176.35 (13) | C12'—O2'—C9'—C10' | −2.1 (2) |
| C12—O2—C9—C10 | −3.6 (2) | C12'—O2'—C9'—C8' | 177.49 (13) |
| C7—C8—C9—O2 | −179.13 (12) | C7'—C8'—C9'—O2' | −178.38 (12) |
| C7—C8—C9—C10 | 0.8 (2) | C7'—C8'—C9'—C10' | 1.2 (2) |
| O2—C9—C10—C11 | 178.93 (13) | O2'—C9'—C10'—C11' | 178.20 (13) |
| C8—C9—C10—C11 | −1.0 (2) | C8'—C9'—C10'—C11' | −1.4 (2) |
| C9—C10—C11—C6 | 0.4 (2) | C9'—C10'—C11'—C6' | 1.0 (2) |
| C7—C6—C11—C10 | 0.5 (2) | C7'—C6'—C11'—C10' | −0.4 (2) |
| C5—C6—C11—C10 | 179.72 (13) | C5'—C6'—C11'—C10' | 179.86 (13) |
| C9—O2—C12—C13 | −174.97 (12) | C9'—O2'—C12'—C13' | −173.82 (13) |
| C2—N1—C14—C19 | −50.0 (2) | C2'—N1'—C14'—C19' | −60.2 (2) |
| C2—N1—C14—C15 | 131.93 (18) | C2'—N1'—C14'—C15' | 122.06 (18) |
| C19—C14—C15—C16 | 0.3 (3) | C19'—C14'—C15'—C16' | 0.9 (3) |
| N1—C14—C15—C16 | 178.35 (18) | N1'—C14'—C15'—C16' | 178.60 (16) |
| C14—C15—C16—C17 | 1.6 (3) | C14'—C15'—C16'—C17' | 0.4 (3) |
| C15—C16—C17—C18 | −2.2 (3) | C20'—O3'—C17'—C16' | −179.90 (16) |
| C15—C16—C17—O3 | 178.87 (19) | C20'—O3'—C17'—C18' | −0.1 (3) |
| C20—O3—C17—C18 | 0.9 (3) | C15'—C16'—C17'—O3' | 179.18 (16) |
| C20—O3—C17—C16 | 179.71 (18) | C15'—C16'—C17'—C18' | −0.6 (3) |
| C16—C17—C18—C19 | 0.9 (3) | O3'—C17'—C18'—C19' | 179.81 (17) |
| O3—C17—C18—C19 | 179.73 (17) | C16'—C17'—C18'—C19' | −0.4 (3) |
| C15—C14—C19—C18 | −1.6 (3) | C15'—C14'—C19'—C18' | −2.0 (3) |
| N1—C14—C19—C18 | −179.64 (16) | N1'—C14'—C19'—C18' | −179.66 (15) |
| C17—C18—C19—C14 | 1.0 (3) | C17'—C18'—C19'—C14' | 1.7 (3) |
| D—H···A | D—H | H···A | D···A | D—H···A |
| N1—H01···S' | 0.83 (1) | 2.74 (1) | 3.4483 (14) | 146 (1) |
| N4—H04···O1'i | 0.81 (1) | 2.02 (1) | 2.8156 (17) | 168 (2) |
| N1'—H01'···Sii | 0.82 (1) | 2.66 (1) | 3.3772 (14) | 148 (1) |
| N4'—H04'···O1i | 0.84 (1) | 2.01 (1) | 2.8228 (18) | 164 (2) |
| C11'—H11'···O1i | 0.95 | 2.41 | 3.3378 (19) | 166 |
| C11—H11···O1'i | 0.95 | 2.38 | 3.2927 (18) | 162 |
| C20—H20B···Siii | 0.98 | 2.98 | 3.9215 (17) | 161 |
| C20'—H20E···S'iv | 0.98 | 2.92 | 3.8936 (18) | 175 |
| C10'—H10'···Si | 0.95 | 2.83 | 3.7559 (17) | 166 |
| C10—H10···S'i | 0.95 | 2.81 | 3.7369 (17) | 166 |
| C15'—H15'···Sii | 0.95 | 3.05 | 3.6482 (16) | 123 |
| C15—H15···S' | 0.95 | 2.94 | 3.6925 (17) | 137 |
| N3'—H03'···Cg | 0.85 (1) | 2.53 | 3.25 | 144 |
| N3—H03···Cg'v | 0.82 (1) | 2.65 | 3.29 | 135 |
| Symmetry codes: (i) −x+1, y+1/2, −z+1; (ii) x, y, z−1; (iii) −x+2, y+1/2, −z+2; (iv) −x+2, y+1/2, −z+1; (v) x, y, z+1. |
| D—H···A | D—H | H···A | D···A | D—H···A |
| N1—H01···S' | 0.83 (1) | 2.74 (1) | 3.4483 (14) | 146 (1) |
| N4—H04···O1'i | 0.81 (1) | 2.02 (1) | 2.8156 (17) | 168 (2) |
| N1'—H01'···Sii | 0.82 (1) | 2.66 (1) | 3.3772 (14) | 148 (1) |
| N4'—H04'···O1i | 0.84 (1) | 2.01 (1) | 2.8228 (18) | 164 (2) |
| C11'—H11'···O1i | 0.95 | 2.41 | 3.3378 (19) | 166 |
| C11—H11···O1'i | 0.95 | 2.38 | 3.2927 (18) | 162 |
| C20—H20B···Siii | 0.98 | 2.98 | 3.9215 (17) | 161 |
| C20'—H20E···S'iv | 0.98 | 2.92 | 3.8936 (18) | 175 |
| C10'—H10'···Si | 0.95 | 2.83 | 3.7559 (17) | 166 |
| C10—H10···S'i | 0.95 | 2.81 | 3.7369 (17) | 166 |
| C15'—H15'···Sii | 0.95 | 3.05 | 3.6482 (16) | 123 |
| C15—H15···S' | 0.95 | 2.94 | 3.6925 (17) | 137 |
| N3'—H03'···Cg | 0.85 (1) | 2.53 | 3.25 | 144 |
| N3—H03···Cg'v | 0.82 (1) | 2.65 | 3.29 | 135 |
| Symmetry codes: (i) −x+1, y+1/2, −z+1; (ii) x, y, z−1; (iii) −x+2, y+1/2, −z+2; (iv) −x+2, y+1/2, −z+1; (v) x, y, z+1. |
Al-Masoudi, I. A., Al-Soud, Y. A., Al-Salihi, N. J. & Al-Masoudi, N. A. (2006). Chem. Heterocycl. Comp. 42, 1377–1403.
Angelusiu, M. V., Almajan, G. L., Rosu, T., Negoiu, M., Almajan, E. R. & Roy, J. (2009). Eur. J. Med. Chem. 44, 3323–3329.
Flack, H. D. (1983). Acta Cryst. A39, 876–881.
Ghosh, S., Mishra, A. K. & Bhatia, G. (2009). Bioorg. Med. Chem. Lett. 19, 386–389.
Kucukguzel, S. G., Kucukguzel, I., Tatar, E. & Rollas, S. (2007). Eur. J. Med. Chem. 42, 893–901.
Liu, J., Cao, R., Yi, W., Ma, C., Wan, Y., Zhou, B., Ma, L. & Song, H. (2009). Eur. J. Med. Chem. 44, 1773–1778.
Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd., Yarnton, Oxford, UK.
Serwar, M., Akhtar, T., Hameed, S. & Khan, K. M. (2009). ARKIVOC pp. 210–221.
Serwer, M., Khawar Rauf, M., Ebihara, M. & Hameed, S. (2008). Acta Cryst. E64, o812.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.
Siemens (1994). XP. Siemens Analytical X-ray Instruments, Madison, U.S.A.
Tomascikava, J., Imrich, J. & Danihel, I. (2008). Molecules 13, 501–518.
Tozkoparan, B., Kupeli, E., Yesilada, E. & Ertan, M. (2007). Bioorg. Med. Chem. 15, 1808–1814.
Thiosemicarbazides represent a class of versatile precursors for the syntheses of various nitrogen heterocycles (Kucukguzel et al., 2007; Al-Masoudi et al., 2006; Tozkoparan et al., 2007; Tomascikava et al., 2008; Serwer et al. 2008; Serwar et al. 2009). The thiosemicarbazide moiety possesses substantial pharmaceutical potential such as anti-tumor (Angelusiu et al., 2009), tyrosinase inhibitor (Liu et al., 2009) and antioxidant (Ghosh et al., 2009) properties. The title compound was synthesized as an intermediate for its onward conversion to 1,2,4-triazoles and 1,3,4-thiadiazoles and in order to explore their anti-bacterial, urease inhibition and anti-fungal activities.
The title compound crystallizes with two independent molecules in the asymmetric unit (Fig. 1); these are related to a good approximation by a translation of c/2. A least-squares fit of both molecules gives an r.m.s. deviation of 0.15 Å for all non-H atoms. Main differences involve orientations of the aromatic rings, e.g. C2—N1—C14—C15 131.9 (2), 122.1 (2)°. Atoms of the second independent molecule are distinguished by a prime (') where necessary. Molecular dimensions (e.g. the hydrazine N—N bond lengths of 1.393 (2), 1.391 (2) Å) may be regarded as normal. The thione sulfur is trans to N4 across the bond C2—N3 (torsion angles 174.8 (1), 172.2 (1)°) but cis to C14 across the bond N1—C2 (torsion angles -9.0 (2), -8.1 (2)).
Each molecule consists of three approximately planar moieties with various common atoms: (1) the central thioamide section (S, N2, N3, N4, C2, C14); (2) the hydrazine and its aromatic ring (C5–13, O1, O2, N3, N4); and (3) the amide and its aromatic ring (C14–20, N1, O3). These display r.m.s. deviations of 0.07, 0.05, 0.01 Å in molecule 1 and 0.08, 0.06, 0.01 Å in molecule 2. Interplanar angles (1)–(2) and (3)–(2) are 68.09 (3), 56.56 (4)° in molecule 1 and 77.22 (3), 66.14 (3)° in molecule 2.
The molecular packing is three-dimensional; classical and "weak" hydrogen bonds are summarized in Table 2. Both molecules form a topologically equivalent set of hydrogen bonds. Fig. 2 shows that the molecules associate to form layers parallel to the xz plane; within the layers, the molecules are linked by classical H bonds N1—H01···S' (and N1'—H01'···S), whereas the layers are linked by N4—H04···O1' and the weak H bonds C10—H10···S' and C11—H11···O1' (and their counterparts). The H bond donors N3—H03 and N03'—H03' are involved in C—H···π interactions to the centroids of the ring C6'–11' and C6–11 respectively, with H···π 2.65, 2.53 Å and angles 135°, 144° respectively (operators x,y,1 + z, and x,y,z). These interactions are not shown explicitly in Fig. 2 but can be recognized within the layers.