supplementary materials
3,3'-Dibenzoyl-1,1'-(3,6-dioxaoctane-1,8-diyl)dithiourea
In the molecule of the title compound, C22H26N4O4S2, the central O-CH2-CH2-O chain adopts a synclinal conformation [torsion angle = 65.0 (2)°]. The crystal structure is stabilized by intramolecular N-H
O=C and intermolecular N-HO-C hydrogen bonds.
Benzoyl chloride (7.10 g, 50 mmol) was reacted with potassium thiocyanate (4.86 g, 50 mmol) in CH3OCH3 (50 ml) solution, to give the corresponding benzoyl
isothiocyanate after one hour under refluxing. After cooling to room
temperature, a solution of 2-(2-(2-aminoethoxy)ethoxy)ethanamine (3.70 g, 25 mmol) in CH3OCH3 (20 ml) was added dropwise to benzoyl isothiocyanate.
After three hours under stirring, 200 ml of HCl 1 M was added. A yellow
oil was isolated and treated with diethyl ether to give the title compound
which is washed with diethyl ether twice. Yield: 55.9%. m.p. 415–419 K. Anal.
Calc. for C22H26N4O4S2: C 55.68, H 5.52, N 11.81%. Found: C 55.70, H
5.45, N 11.65%. Selected IR data (cm-1, KBr pellet): 3424, 3218 (ν NH),
1667 (ν C?O), 1160 (ν C?S). 1H-NMR (200 MHz, DMSO-d6, δ, p.p.m.): 3.45
(t, 4H, N—CH2); 3.63 (s, 4H, O—CH2); 3.70 (t, 4H, O—CH2);
7.21–7.92 (m, 10H, C6H5); 11.01 (s, 2H, NH); 11.41 (s, 2H, NH). 13C-NMR
(50 MHz, DMSO-d6, δ, p.p.m.): 45.21 (N—CH2); 68.09 (O—CH2); 70.12
(O—CH2); 133.31–127.62 (C6H5); 1168.60 (C?O); 180.81 (C?S). A CH3Cl
solution of the title compound was mixed with ethanol (1/1). After several
days, colorless block-shaped single crystals suitable for X-ray
crystallographic analysis were obtained.
H atoms of NH groups were located in a difference map and refined freely. Others
H atoms were placed geometrically and refined with a riding model.
Uiso(H) for H was calculated as 1.2 Ueq of the carrier atom.
Data collection: COLLECT (Nonius, 1998); cell refinement: DENZO and SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO and SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).
3,3'-Dibenzoyl-1,1'-(3,6-dioxaoctane-1,8-diyl)dithiourea
top
Crystal data top
| C22H26N4O4S2 | Z = 2 |
| Mr = 474.59 | F(000) = 500 |
| Triclinic, P1 | Dx = 1.347 Mg m−3 |
| Hall symbol: -P 1 | Melting point: 415 K |
| a = 7.9718 (2) Å | Mo Kα radiation, λ = 0.71073 Å |
| b = 9.2177 (3) Å | Cell parameters from 4206 reflections |
| c = 16.4106 (5) Å | θ = 1.0–25.4° |
| α = 81.018 (2)° | µ = 0.26 mm−1 |
| β = 83.364 (2)° | T = 293 K |
| γ = 80.450 (2)° | Prism, yellow |
| V = 1169.60 (6) Å3 | 0.10 × 0.10 × 0.10 mm |
Data collection top
Nonius KappaCCD
diffractometer | 2737 reflections with I > 2σ(I) |
| Radiation source: fine-focus sealed tube | Rint = 0.030 |
| graphite | θmax = 25.2°, θmin = 2.3° |
| ω scans | h = −9→9 |
| 7989 measured reflections | k = −11→11 |
| 4211 independent reflections | l = −19→19 |
Refinement top
| 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)] = 0.045 | Hydrogen site location: inferred from neighbouring sites |
| wR(F2) = 0.128 | H atoms treated by a mixture of independent and constrained refinement |
| S = 1.02 | w = 1/[σ2(Fo2) + (0.0614P)2 + 0.2609P]
where P = (Fo2 + 2Fc2)/3 |
| 4211 reflections | (Δ/σ)max = 0.008 |
| 305 parameters | Δρmax = 0.41 e Å−3 |
| 0 restraints | Δρmin = −0.50 e Å−3 |
| 0 constraints | |
Crystal data top
| C22H26N4O4S2 | γ = 80.450 (2)° |
| Mr = 474.59 | V = 1169.60 (6) Å3 |
| Triclinic, P1 | Z = 2 |
| a = 7.9718 (2) Å | Mo Kα radiation |
| b = 9.2177 (3) Å | µ = 0.26 mm−1 |
| c = 16.4106 (5) Å | T = 293 K |
| α = 81.018 (2)° | 0.10 × 0.10 × 0.10 mm |
| β = 83.364 (2)° | |
Data collection top
Nonius KappaCCD
diffractometer | 2737 reflections with I > 2σ(I) |
| 7989 measured reflections | Rint = 0.030 |
| 4211 independent reflections | θmax = 25.2° |
Refinement top
| R[F2 > 2σ(F2)] = 0.045 | H atoms treated by a mixture of independent and constrained refinement |
| wR(F2) = 0.128 | Δρmax = 0.41 e Å−3 |
| S = 1.02 | Δρmin = −0.50 e Å−3 |
| 4211 reflections | Absolute structure: ? |
| 305 parameters | Flack parameter: ? |
| 0 restraints | Rogers parameter: ? |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top| | x | y | z | Uiso*/Ueq | |
| S1 | 0.37094 (10) | 0.16706 (9) | 0.86251 (5) | 0.0713 (3) | |
| S2 | 1.26452 (13) | −0.27342 (8) | 0.52516 (4) | 0.0790 (3) | |
| O1 | 0.7377 (3) | 0.4586 (2) | 0.91685 (11) | 0.0711 (6) | |
| O2 | 0.81088 (19) | 0.39803 (17) | 0.67050 (9) | 0.0482 (4) | |
| O3 | 1.12041 (19) | 0.24744 (17) | 0.60508 (10) | 0.0472 (4) | |
| O4 | 1.2463 (3) | 0.1608 (2) | 0.35665 (11) | 0.0740 (6) | |
| N1 | 0.5641 (3) | 0.2839 (3) | 0.94678 (14) | 0.0527 (6) | |
| H1 | 0.530 (3) | 0.224 (3) | 0.9815 (16) | 0.049 (8)* | |
| N2 | 0.5680 (3) | 0.3729 (2) | 0.80784 (13) | 0.0492 (5) | |
| H2 | 0.639 (3) | 0.422 (3) | 0.8172 (16) | 0.056 (8)* | |
| N3 | 1.2498 (3) | 0.0165 (3) | 0.50822 (13) | 0.0506 (5) | |
| H3 | 1.236 (3) | 0.099 (3) | 0.4798 (17) | 0.063 (9)* | |
| N4 | 1.2073 (3) | −0.0786 (2) | 0.39123 (12) | 0.0465 (5) | |
| H4 | 1.190 (3) | −0.154 (3) | 0.3741 (15) | 0.052 (8)* | |
| C1 | 0.7116 (3) | 0.3433 (3) | 1.05616 (14) | 0.0456 (6) | |
| C2 | 0.8101 (3) | 0.4370 (3) | 1.08034 (16) | 0.0539 (6) | |
| H2A | 0.8497 | 0.5115 | 1.0416 | 0.065* | |
| C3 | 0.8498 (4) | 0.4211 (3) | 1.16088 (18) | 0.0639 (7) | |
| H3A | 0.9169 | 0.4840 | 1.1763 | 0.077* | |
| C4 | 0.7902 (4) | 0.3120 (3) | 1.21864 (18) | 0.0692 (8) | |
| H4A | 0.8165 | 0.3012 | 1.2732 | 0.083* | |
| C5 | 0.6923 (4) | 0.2194 (4) | 1.19573 (19) | 0.0771 (9) | |
| H5 | 0.6513 | 0.1464 | 1.2350 | 0.093* | |
| C6 | 0.6537 (4) | 0.2335 (3) | 1.11472 (17) | 0.0649 (8) | |
| H6 | 0.5885 | 0.1690 | 1.0995 | 0.078* | |
| C7 | 0.6744 (3) | 0.3674 (3) | 0.96796 (15) | 0.0488 (6) | |
| C8 | 0.5078 (3) | 0.2817 (3) | 0.86956 (15) | 0.0477 (6) | |
| C9 | 0.5275 (3) | 0.3838 (3) | 0.72324 (15) | 0.0537 (6) | |
| H9A | 0.4095 | 0.4293 | 0.7189 | 0.064* | |
| H9B | 0.5406 | 0.2851 | 0.7075 | 0.064* | |
| C10 | 0.6419 (3) | 0.4745 (3) | 0.66582 (15) | 0.0516 (6) | |
| H10A | 0.6101 | 0.4859 | 0.6096 | 0.062* | |
| H10B | 0.6331 | 0.5723 | 0.6822 | 0.062* | |
| C11 | 0.9346 (3) | 0.4733 (3) | 0.61860 (16) | 0.0522 (6) | |
| H11A | 0.9278 | 0.5730 | 0.6320 | 0.063* | |
| H11B | 0.9133 | 0.4804 | 0.5610 | 0.063* | |
| C12 | 1.1067 (3) | 0.3882 (3) | 0.63208 (16) | 0.0506 (6) | |
| H12A | 1.1936 | 0.4426 | 0.6014 | 0.061* | |
| H12B | 1.1243 | 0.3751 | 0.6904 | 0.061* | |
| C13 | 1.2832 (3) | 0.1611 (3) | 0.61572 (16) | 0.0529 (6) | |
| H13A | 1.3092 | 0.1538 | 0.6727 | 0.063* | |
| H13B | 1.3705 | 0.2077 | 0.5799 | 0.063* | |
| C14 | 1.2803 (3) | 0.0091 (3) | 0.59436 (14) | 0.0504 (6) | |
| H14A | 1.3887 | −0.0529 | 0.6045 | 0.061* | |
| H14B | 1.1912 | −0.0359 | 0.6297 | 0.061* | |
| C15 | 1.2389 (3) | −0.1016 (3) | 0.47501 (14) | 0.0447 (6) | |
| C16 | 1.2118 (3) | 0.0483 (3) | 0.33592 (14) | 0.0454 (6) | |
| C17 | 1.1796 (3) | 0.0433 (2) | 0.24907 (14) | 0.0419 (5) | |
| C18 | 1.2227 (3) | 0.1595 (3) | 0.19018 (15) | 0.0527 (6) | |
| H18 | 1.2684 | 0.2361 | 0.2062 | 0.063* | |
| C19 | 1.1984 (3) | 0.1624 (3) | 0.10851 (16) | 0.0610 (7) | |
| H19 | 1.2299 | 0.2398 | 0.0693 | 0.073* | |
| C20 | 1.1281 (3) | 0.0520 (3) | 0.08436 (16) | 0.0618 (7) | |
| H20 | 1.1120 | 0.0546 | 0.0289 | 0.074* | |
| C21 | 1.0811 (3) | −0.0632 (3) | 0.14224 (16) | 0.0605 (7) | |
| H21 | 1.0324 | −0.1378 | 0.1260 | 0.073* | |
| C22 | 1.1069 (3) | −0.0672 (3) | 0.22467 (15) | 0.0507 (6) | |
| H22 | 1.0751 | −0.1446 | 0.2638 | 0.061* | |
Atomic displacement parameters (Å2) top| | U11 | U22 | U33 | U12 | U13 | U23 |
| S1 | 0.0807 (5) | 0.0781 (5) | 0.0659 (5) | −0.0445 (4) | −0.0032 (4) | −0.0115 (4) |
| S2 | 0.1467 (8) | 0.0464 (4) | 0.0494 (4) | −0.0296 (5) | −0.0275 (5) | 0.0059 (3) |
| O1 | 0.0906 (14) | 0.0822 (14) | 0.0503 (11) | −0.0502 (12) | −0.0123 (10) | 0.0050 (10) |
| O2 | 0.0498 (10) | 0.0443 (9) | 0.0461 (9) | −0.0077 (8) | 0.0014 (8) | 0.0036 (7) |
| O3 | 0.0497 (10) | 0.0457 (9) | 0.0501 (10) | −0.0119 (8) | −0.0053 (7) | −0.0140 (8) |
| O4 | 0.1328 (18) | 0.0430 (11) | 0.0518 (11) | −0.0288 (11) | −0.0176 (11) | −0.0010 (9) |
| N1 | 0.0584 (14) | 0.0572 (14) | 0.0453 (13) | −0.0237 (11) | 0.0023 (11) | −0.0054 (11) |
| N2 | 0.0468 (12) | 0.0626 (14) | 0.0431 (12) | −0.0214 (11) | 0.0000 (10) | −0.0112 (10) |
| N3 | 0.0716 (15) | 0.0397 (13) | 0.0409 (12) | −0.0077 (11) | −0.0081 (10) | −0.0055 (10) |
| N4 | 0.0666 (14) | 0.0372 (12) | 0.0385 (11) | −0.0162 (10) | −0.0079 (9) | −0.0024 (9) |
| C1 | 0.0450 (13) | 0.0445 (14) | 0.0455 (14) | −0.0027 (11) | −0.0034 (11) | −0.0053 (11) |
| C2 | 0.0562 (15) | 0.0556 (16) | 0.0514 (15) | −0.0127 (13) | −0.0023 (12) | −0.0093 (12) |
| C3 | 0.0698 (18) | 0.0677 (18) | 0.0579 (17) | −0.0074 (15) | −0.0134 (14) | −0.0177 (15) |
| C4 | 0.076 (2) | 0.078 (2) | 0.0507 (17) | 0.0048 (17) | −0.0169 (15) | −0.0081 (16) |
| C5 | 0.087 (2) | 0.080 (2) | 0.0591 (19) | −0.0181 (18) | −0.0171 (16) | 0.0192 (16) |
| C6 | 0.0748 (19) | 0.0598 (17) | 0.0612 (18) | −0.0203 (15) | −0.0184 (15) | 0.0077 (14) |
| C7 | 0.0483 (14) | 0.0492 (15) | 0.0496 (15) | −0.0124 (12) | −0.0012 (12) | −0.0062 (12) |
| C8 | 0.0461 (13) | 0.0507 (15) | 0.0486 (15) | −0.0121 (11) | 0.0023 (11) | −0.0135 (12) |
| C9 | 0.0498 (15) | 0.0667 (17) | 0.0491 (15) | −0.0132 (13) | −0.0048 (12) | −0.0167 (13) |
| C10 | 0.0562 (15) | 0.0521 (15) | 0.0451 (14) | −0.0026 (12) | −0.0084 (12) | −0.0056 (12) |
| C11 | 0.0639 (16) | 0.0404 (14) | 0.0514 (15) | −0.0188 (12) | 0.0041 (12) | 0.0006 (11) |
| C12 | 0.0578 (15) | 0.0444 (14) | 0.0527 (15) | −0.0208 (12) | 0.0023 (12) | −0.0082 (12) |
| C13 | 0.0527 (15) | 0.0607 (16) | 0.0485 (15) | −0.0100 (13) | −0.0065 (12) | −0.0144 (12) |
| C14 | 0.0612 (16) | 0.0531 (15) | 0.0379 (13) | −0.0040 (12) | −0.0102 (11) | −0.0100 (11) |
| C15 | 0.0512 (14) | 0.0442 (14) | 0.0399 (13) | −0.0115 (11) | −0.0051 (11) | −0.0044 (11) |
| C16 | 0.0543 (14) | 0.0392 (14) | 0.0426 (13) | −0.0097 (11) | −0.0041 (11) | −0.0023 (11) |
| C17 | 0.0440 (13) | 0.0396 (13) | 0.0399 (13) | −0.0052 (10) | −0.0027 (10) | −0.0009 (10) |
| C18 | 0.0591 (16) | 0.0488 (15) | 0.0492 (15) | −0.0153 (12) | −0.0033 (12) | 0.0029 (12) |
| C19 | 0.0667 (18) | 0.0656 (18) | 0.0458 (16) | −0.0163 (15) | −0.0043 (13) | 0.0132 (13) |
| C20 | 0.0631 (17) | 0.080 (2) | 0.0399 (14) | −0.0112 (15) | −0.0098 (13) | 0.0033 (14) |
| C21 | 0.0691 (17) | 0.0629 (17) | 0.0527 (16) | −0.0161 (14) | −0.0134 (13) | −0.0059 (13) |
| C22 | 0.0572 (15) | 0.0500 (15) | 0.0434 (14) | −0.0135 (12) | −0.0065 (12) | 0.0052 (11) |
Geometric parameters (Å, °) top
| S1—C8 | 1.665 (3) | C5—H5 | 0.9300 |
| S2—C15 | 1.659 (2) | C6—H6 | 0.9300 |
| O1—C7 | 1.220 (3) | C9—C10 | 1.492 (3) |
| O2—C10 | 1.417 (3) | C9—H9A | 0.9700 |
| O2—C11 | 1.424 (3) | C9—H9B | 0.9700 |
| O3—C12 | 1.419 (3) | C10—H10A | 0.9700 |
| O3—C13 | 1.419 (3) | C10—H10B | 0.9700 |
| O4—C16 | 1.222 (3) | C11—C12 | 1.485 (3) |
| N1—C7 | 1.366 (3) | C11—H11A | 0.9700 |
| N1—C8 | 1.396 (3) | C11—H11B | 0.9700 |
| N1—H1 | 0.79 (3) | C12—H12A | 0.9700 |
| N2—C8 | 1.311 (3) | C12—H12B | 0.9700 |
| N2—C9 | 1.446 (3) | C13—C14 | 1.501 (3) |
| N2—H2 | 0.82 (3) | C13—H13A | 0.9700 |
| N3—C15 | 1.310 (3) | C13—H13B | 0.9700 |
| N3—C14 | 1.451 (3) | C14—H14A | 0.9700 |
| N3—H3 | 0.83 (3) | C14—H14B | 0.9700 |
| N4—C16 | 1.367 (3) | C16—C17 | 1.486 (3) |
| N4—C15 | 1.404 (3) | C17—C22 | 1.382 (3) |
| N4—H4 | 0.82 (3) | C17—C18 | 1.386 (3) |
| C1—C6 | 1.382 (3) | C18—C19 | 1.372 (4) |
| C1—C2 | 1.387 (3) | C18—H18 | 0.9300 |
| C1—C7 | 1.486 (3) | C19—C20 | 1.369 (4) |
| C2—C3 | 1.375 (4) | C19—H19 | 0.9300 |
| C2—H2A | 0.9300 | C20—C21 | 1.380 (4) |
| C3—C4 | 1.376 (4) | C20—H20 | 0.9300 |
| C3—H3A | 0.9300 | C21—C22 | 1.386 (4) |
| C4—C5 | 1.366 (4) | C21—H21 | 0.9300 |
| C4—H4A | 0.9300 | C22—H22 | 0.9300 |
| C5—C6 | 1.381 (4) | | |
| | | |
| C10—O2—C11 | 113.12 (18) | H10A—C10—H10B | 108.5 |
| C12—O3—C13 | 112.15 (18) | O2—C11—C12 | 108.43 (19) |
| C7—N1—C8 | 129.4 (2) | O2—C11—H11A | 110.0 |
| C7—N1—H1 | 117.6 (19) | C12—C11—H11A | 110.0 |
| C8—N1—H1 | 112.9 (19) | O2—C11—H11B | 110.0 |
| C8—N2—C9 | 124.1 (2) | C12—C11—H11B | 110.0 |
| C8—N2—H2 | 117.9 (18) | H11A—C11—H11B | 108.4 |
| C9—N2—H2 | 117.9 (19) | O3—C12—C11 | 109.5 (2) |
| C15—N3—C14 | 122.6 (2) | O3—C12—H12A | 109.8 |
| C15—N3—H3 | 119 (2) | C11—C12—H12A | 109.8 |
| C14—N3—H3 | 118 (2) | O3—C12—H12B | 109.8 |
| C16—N4—C15 | 127.9 (2) | C11—C12—H12B | 109.8 |
| C16—N4—H4 | 118.1 (18) | H12A—C12—H12B | 108.2 |
| C15—N4—H4 | 113.8 (18) | O3—C13—C14 | 108.6 (2) |
| C6—C1—C2 | 118.7 (2) | O3—C13—H13A | 110.0 |
| C6—C1—C7 | 123.7 (2) | C14—C13—H13A | 110.0 |
| C2—C1—C7 | 117.6 (2) | O3—C13—H13B | 110.0 |
| C3—C2—C1 | 120.8 (3) | C14—C13—H13B | 110.0 |
| C3—C2—H2A | 119.6 | H13A—C13—H13B | 108.4 |
| C1—C2—H2A | 119.6 | N3—C14—C13 | 111.0 (2) |
| C2—C3—C4 | 119.8 (3) | N3—C14—H14A | 109.4 |
| C2—C3—H3A | 120.1 | C13—C14—H14A | 109.4 |
| C4—C3—H3A | 120.1 | N3—C14—H14B | 109.4 |
| C5—C4—C3 | 119.9 (3) | C13—C14—H14B | 109.4 |
| C5—C4—H4A | 120.0 | H14A—C14—H14B | 108.0 |
| C3—C4—H4A | 120.0 | N3—C15—N4 | 116.7 (2) |
| C4—C5—C6 | 120.5 (3) | N3—C15—S2 | 124.06 (19) |
| C4—C5—H5 | 119.7 | N4—C15—S2 | 119.18 (18) |
| C6—C5—H5 | 119.7 | O4—C16—N4 | 121.1 (2) |
| C5—C6—C1 | 120.2 (3) | O4—C16—C17 | 121.1 (2) |
| C5—C6—H6 | 119.9 | N4—C16—C17 | 117.8 (2) |
| C1—C6—H6 | 119.9 | C22—C17—C18 | 119.0 (2) |
| O1—C7—N1 | 121.3 (2) | C22—C17—C16 | 124.1 (2) |
| O1—C7—C1 | 121.7 (2) | C18—C17—C16 | 116.9 (2) |
| N1—C7—C1 | 117.0 (2) | C19—C18—C17 | 120.5 (3) |
| N2—C8—N1 | 116.1 (2) | C19—C18—H18 | 119.8 |
| N2—C8—S1 | 125.2 (2) | C17—C18—H18 | 119.8 |
| N1—C8—S1 | 118.66 (18) | C20—C19—C18 | 120.4 (2) |
| N2—C9—C10 | 110.6 (2) | C20—C19—H19 | 119.8 |
| N2—C9—H9A | 109.5 | C18—C19—H19 | 119.8 |
| C10—C9—H9A | 109.5 | C19—C20—C21 | 120.1 (3) |
| N2—C9—H9B | 109.5 | C19—C20—H20 | 120.0 |
| C10—C9—H9B | 109.5 | C21—C20—H20 | 120.0 |
| H9A—C9—H9B | 108.1 | C20—C21—C22 | 119.7 (3) |
| O2—C10—C9 | 107.14 (19) | C20—C21—H21 | 120.1 |
| O2—C10—H10A | 110.3 | C22—C21—H21 | 120.1 |
| C9—C10—H10A | 110.3 | C17—C22—C21 | 120.3 (2) |
| O2—C10—H10B | 110.3 | C17—C22—H22 | 119.8 |
| C9—C10—H10B | 110.3 | C21—C22—H22 | 119.8 |
| | | |
| O2—C11—C12—O3 | 65.0 (2) | | |
Hydrogen-bond geometry (Å, °) top
| D—H···A | D—H | H···A | D···A | D—H···A |
| N2—H2···O1 | 0.82 (3) | 1.99 (3) | 2.648 (3) | 136 (2) |
| N3—H3···O4 | 0.83 (3) | 2.01 (3) | 2.632 (3) | 132 (3) |
| N4—H4···O2i | 0.82 (3) | 2.48 (3) | 3.290 (3) | 170 (2) |
| Symmetry codes: (i) −x+2, −y, −z+1. |
Table 1
Hydrogen-bond geometry (Å, °) top
| D—H···A | D—H | H···A | D···A | D—H···A |
| N2—H2···O1 | 0.82 (3) | 1.99 (3) | 2.648 (3) | 136 (2) |
| N3—H3···O4 | 0.83 (3) | 2.01 (3) | 2.632 (3) | 132 (3) |
| N4—H4···O2i | 0.82 (3) | 2.48 (3) | 3.290 (3) | 170 (2) |
| Symmetry codes: (i) −x+2, −y, −z+1. |
The authors thank the Agence Universitaire de la Francophonie for financial
support (AUF-PSCI No.6314PS804).
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![[Figure 1]](./bh2217fig1thm.gif)
![[Figure 2]](./bh2217fig2thm.gif)
The title compound, C22H26N4O4S2, was characterized by 1H and 13C NMR, solid-state IR and X-ray crystallographic techniques. The X-ray structure determination reveals that the compound crystallizes in the triclinic space group P1 with one molecule in the asymmetric unit. The molecular geometry is illustrated in Fig. 1. The C—S bond lengths of 1.665 (3) Å and 1.659 (2) Å and the C—O bond lengths of 1.220 (3) Å and 1.222 (3) Å are double bonds character and are comparable to those observed for 1-(biphenyl-4-carbonyl)-3-p-tolyl-thiourea [1.647 (3) Å for C—S, 1.217 (3) and 1.224 (3) Å for C—O respectively (Arslan et al., 2004)]. The C—N bond lengths are in the range 1.310 (3)–1.451 (3) Å, and are shorter than the normal single C—N bond length (Avşar et al., 2003). The carbonyl group forms an intramolecular hydrogen bonds with the N2—H2 and the N3—H3 groups, which forms two six-membered rings (C8/N1/C7/O1/H2/N2 and C15/N4/C16/O4/H3/N3) structure (Fig. 2); H2···O1 and the H3···O4 separations are respectively 1.99 (3) Å and 2.01 (3) Å. There is an intermolecular hydrogen bonding between N4—H4 and the O atom of the ethoxy group of a symmetry-related molecule, the H4···O2 (-x + 2, -y, -z + 1) separation being 2.48 (3) Å (Table 1). The structure of the title compound is related to other thiourea derivatives (e.g. Ding et al., 2008; Du & Du, 2008).