Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803010110/cv6191sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536803010110/cv6191Isup2.hkl |
CCDC reference: 214829
A solution of benzhydrazide (1.62 g, 0.011 mol) in acetone (50 ml) was added dropwise to 50 ml of an acetone solution containing an equimolar amount of benzoylisothiocyanate in a two-necked round-bottomed flask. The solution was refluxed for about 2 h and then cooled in ice. The white precipitate was filtered off and washed with ethanol-distilled water, then dried in a vacuum (yield 83%). Recrystallization from ethanol yielded single crystals suitable for X-ray analysis.
After checking their presence in the difference map, all H atoms were fixed geometrically and allowed to ride on the parent C or N atoms, with C—H = 0.93 Å and N—H = 0.86 Å.
Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL (Sheldrick, 1997); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 1990).
C15H13N3O2S | F(000) = 624 |
Mr = 299.34 | Dx = 1.412 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 14.7949 (19) Å | Cell parameters from 1584 reflections |
b = 7.7004 (10) Å | θ = 1.6–27.5° |
c = 13.9577 (18) Å | µ = 0.24 mm−1 |
β = 117.705 (2)° | T = 273 K |
V = 1407.8 (3) Å3 | Slab, colourless |
Z = 4 | 0.55 × 0.21 × 0.10 mm |
Bruker SMART APEX CCD area-detector diffractometer | 3097 independent reflections |
Radiation source: fine-focus sealed tube | 1925 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.043 |
Detector resolution: 83.66 pixels mm-1 | θmax = 27.5°, θmin = 1.6° |
ω scans | h = −17→18 |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | k = −9→9 |
Tmin = 0.880, Tmax = 0.977 | l = −18→13 |
7907 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)] = 0.057 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.133 | H-atom parameters constrained |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0304P)2 + 0.1794P] where P = (Fo2 + 2Fc2)/3 |
3097 reflections | (Δ/σ)max < 0.001 |
190 parameters | Δρmax = 0.20 e Å−3 |
0 restraints | Δρmin = −0.19 e Å−3 |
C15H13N3O2S | V = 1407.8 (3) Å3 |
Mr = 299.34 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 14.7949 (19) Å | µ = 0.24 mm−1 |
b = 7.7004 (10) Å | T = 273 K |
c = 13.9577 (18) Å | 0.55 × 0.21 × 0.10 mm |
β = 117.705 (2)° |
Bruker SMART APEX CCD area-detector diffractometer | 3097 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 1925 reflections with I > 2σ(I) |
Tmin = 0.880, Tmax = 0.977 | Rint = 0.043 |
7907 measured reflections |
R[F2 > 2σ(F2)] = 0.057 | 0 restraints |
wR(F2) = 0.133 | H-atom parameters constrained |
S = 1.05 | Δρmax = 0.20 e Å−3 |
3097 reflections | Δρmin = −0.19 e Å−3 |
190 parameters |
x | y | z | Uiso*/Ueq | ||
S1 | 0.19008 (5) | 0.07097 (11) | 0.41368 (6) | 0.0628 (3) | |
O1 | 0.49547 (13) | 0.1887 (3) | 0.43281 (15) | 0.0610 (5) | |
O2 | 0.30605 (14) | 0.0778 (3) | 0.13136 (15) | 0.0602 (6) | |
N1 | 0.37856 (14) | 0.1982 (3) | 0.49423 (16) | 0.0427 (5) | |
H1A | 0.3677 | 0.2337 | 0.5464 | 0.051* | |
N2 | 0.31213 (15) | 0.0790 (3) | 0.32451 (17) | 0.0474 (6) | |
H2A | 0.3688 | 0.1062 | 0.3251 | 0.057* | |
N3 | 0.23692 (16) | −0.0041 (3) | 0.23624 (17) | 0.0513 (6) | |
H3A | 0.1896 | −0.0601 | 0.2424 | 0.062* | |
C1 | 0.54332 (19) | 0.3085 (3) | 0.7024 (2) | 0.0487 (7) | |
H1B | 0.4880 | 0.2551 | 0.7049 | 0.058* | |
C2 | 0.61817 (19) | 0.3866 (4) | 0.7941 (2) | 0.0519 (7) | |
H2B | 0.6133 | 0.3848 | 0.8582 | 0.062* | |
C3 | 0.6996 (2) | 0.4668 (3) | 0.7912 (2) | 0.0503 (7) | |
H3B | 0.7492 | 0.5213 | 0.8527 | 0.060* | |
C4 | 0.7076 (2) | 0.4663 (4) | 0.6969 (2) | 0.0542 (7) | |
H4A | 0.7630 | 0.5202 | 0.6950 | 0.065* | |
C5 | 0.63453 (19) | 0.3868 (3) | 0.6054 (2) | 0.0479 (7) | |
H5A | 0.6414 | 0.3850 | 0.5425 | 0.057* | |
C6 | 0.55034 (17) | 0.3092 (3) | 0.6068 (2) | 0.0398 (6) | |
C7 | 0.47454 (18) | 0.2282 (3) | 0.5049 (2) | 0.0430 (6) | |
C8 | 0.29731 (18) | 0.1172 (3) | 0.4087 (2) | 0.0420 (6) | |
C9 | 0.23762 (19) | 0.0024 (3) | 0.1402 (2) | 0.0432 (6) | |
C10 | 0.15052 (18) | −0.0874 (3) | 0.0494 (2) | 0.0410 (6) | |
C11 | 0.1361 (2) | −0.0548 (4) | −0.0539 (2) | 0.0554 (7) | |
H11A | 0.1808 | 0.0186 | −0.0642 | 0.067* | |
C12 | 0.0556 (2) | −0.1308 (4) | −0.1423 (2) | 0.0662 (9) | |
H12A | 0.0465 | −0.1087 | −0.2118 | 0.079* | |
C13 | −0.0104 (2) | −0.2379 (4) | −0.1279 (3) | 0.0605 (8) | |
H13A | −0.0646 | −0.2883 | −0.1875 | 0.073* | |
C14 | 0.0029 (2) | −0.2711 (4) | −0.0262 (3) | 0.0599 (8) | |
H14A | −0.0423 | −0.3442 | −0.0166 | 0.072* | |
C15 | 0.0835 (2) | −0.1964 (3) | 0.0630 (2) | 0.0531 (7) | |
H15A | 0.0924 | −0.2199 | 0.1322 | 0.064* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0491 (4) | 0.0989 (6) | 0.0431 (5) | −0.0197 (4) | 0.0236 (4) | −0.0082 (4) |
O1 | 0.0516 (11) | 0.0927 (15) | 0.0472 (12) | −0.0114 (10) | 0.0302 (10) | −0.0224 (11) |
O2 | 0.0541 (11) | 0.0819 (14) | 0.0466 (12) | −0.0176 (10) | 0.0250 (10) | −0.0064 (10) |
N1 | 0.0416 (11) | 0.0568 (13) | 0.0318 (12) | −0.0026 (9) | 0.0189 (10) | −0.0048 (10) |
N2 | 0.0425 (11) | 0.0610 (14) | 0.0384 (13) | −0.0084 (10) | 0.0186 (10) | −0.0088 (11) |
N3 | 0.0505 (13) | 0.0657 (14) | 0.0382 (14) | −0.0157 (11) | 0.0209 (11) | −0.0105 (11) |
C1 | 0.0424 (14) | 0.0644 (18) | 0.0448 (17) | −0.0046 (12) | 0.0249 (13) | −0.0025 (13) |
C2 | 0.0512 (16) | 0.0726 (19) | 0.0340 (15) | −0.0008 (14) | 0.0216 (14) | −0.0049 (13) |
C3 | 0.0478 (15) | 0.0590 (17) | 0.0382 (16) | −0.0030 (12) | 0.0150 (13) | −0.0081 (13) |
C4 | 0.0461 (15) | 0.0690 (19) | 0.0501 (18) | −0.0121 (13) | 0.0246 (14) | −0.0035 (14) |
C5 | 0.0490 (15) | 0.0617 (17) | 0.0383 (15) | −0.0042 (13) | 0.0248 (13) | −0.0018 (13) |
C6 | 0.0384 (13) | 0.0452 (14) | 0.0356 (14) | 0.0029 (10) | 0.0171 (12) | −0.0001 (11) |
C7 | 0.0412 (13) | 0.0516 (15) | 0.0396 (16) | 0.0008 (11) | 0.0216 (13) | −0.0009 (12) |
C8 | 0.0453 (14) | 0.0478 (15) | 0.0326 (14) | 0.0015 (11) | 0.0178 (12) | 0.0012 (11) |
C9 | 0.0452 (14) | 0.0465 (15) | 0.0374 (15) | 0.0031 (11) | 0.0187 (13) | −0.0011 (12) |
C10 | 0.0413 (13) | 0.0445 (14) | 0.0372 (15) | 0.0029 (11) | 0.0182 (12) | −0.0032 (12) |
C11 | 0.0553 (16) | 0.071 (2) | 0.0427 (18) | −0.0040 (14) | 0.0255 (14) | −0.0066 (14) |
C12 | 0.0666 (19) | 0.089 (2) | 0.0397 (18) | −0.0009 (17) | 0.0220 (16) | −0.0145 (16) |
C13 | 0.0503 (16) | 0.0607 (19) | 0.055 (2) | 0.0006 (14) | 0.0115 (15) | −0.0169 (15) |
C14 | 0.0500 (16) | 0.0540 (18) | 0.067 (2) | −0.0053 (13) | 0.0204 (16) | −0.0027 (15) |
C15 | 0.0535 (16) | 0.0558 (17) | 0.0482 (18) | −0.0014 (13) | 0.0220 (14) | 0.0016 (14) |
S1—C8 | 1.659 (3) | C4—C5 | 1.375 (4) |
O1—C7 | 1.221 (3) | C4—H4A | 0.9300 |
O2—C9 | 1.222 (3) | C5—C6 | 1.390 (3) |
N1—C7 | 1.376 (3) | C5—H5A | 0.9300 |
N1—C8 | 1.388 (3) | C6—C7 | 1.479 (3) |
N1—H1A | 0.8600 | C9—C10 | 1.493 (3) |
N2—C8 | 1.324 (3) | C10—C15 | 1.378 (3) |
N2—N3 | 1.375 (3) | C10—C11 | 1.379 (4) |
N2—H2A | 0.8600 | C11—C12 | 1.385 (4) |
N3—C9 | 1.346 (3) | C11—H11A | 0.9300 |
N3—H3A | 0.8600 | C12—C13 | 1.362 (4) |
C1—C2 | 1.381 (3) | C12—H12A | 0.9300 |
C1—C6 | 1.385 (3) | C13—C14 | 1.364 (4) |
C1—H1B | 0.9300 | C13—H13A | 0.9300 |
C2—C3 | 1.371 (3) | C14—C15 | 1.387 (4) |
C2—H2B | 0.9300 | C14—H14A | 0.9300 |
C3—C4 | 1.376 (4) | C15—H15A | 0.9300 |
C3—H3B | 0.9300 | ||
C7—N1—C8 | 127.3 (2) | O1—C7—N1 | 120.9 (2) |
C7—N1—H1A | 116.4 | O1—C7—C6 | 121.9 (2) |
C8—N1—H1A | 116.4 | N1—C7—C6 | 117.2 (2) |
C8—N2—N3 | 120.0 (2) | N2—C8—N1 | 115.4 (2) |
C8—N2—H2A | 120.0 | N2—C8—S1 | 123.08 (19) |
N3—N2—H2A | 120.0 | N1—C8—S1 | 121.54 (19) |
C9—N3—N2 | 119.8 (2) | O2—C9—N3 | 120.6 (2) |
C9—N3—H3A | 120.1 | O2—C9—C10 | 124.2 (2) |
N2—N3—H3A | 120.1 | N3—C9—C10 | 115.2 (2) |
C2—C1—C6 | 120.2 (2) | C15—C10—C11 | 119.0 (2) |
C2—C1—H1B | 119.9 | C15—C10—C9 | 123.8 (2) |
C6—C1—H1B | 119.9 | C11—C10—C9 | 117.2 (2) |
C3—C2—C1 | 120.4 (2) | C10—C11—C12 | 120.4 (3) |
C3—C2—H2B | 119.8 | C10—C11—H11A | 119.8 |
C1—C2—H2B | 119.8 | C12—C11—H11A | 119.8 |
C2—C3—C4 | 119.7 (2) | C13—C12—C11 | 120.2 (3) |
C2—C3—H3B | 120.2 | C13—C12—H12A | 119.9 |
C4—C3—H3B | 120.2 | C11—C12—H12A | 119.9 |
C5—C4—C3 | 120.6 (2) | C12—C13—C14 | 120.0 (3) |
C5—C4—H4A | 119.7 | C12—C13—H13A | 120.0 |
C3—C4—H4A | 119.7 | C14—C13—H13A | 120.0 |
C4—C5—C6 | 120.1 (2) | C13—C14—C15 | 120.3 (3) |
C4—C5—H5A | 120.0 | C13—C14—H14A | 119.8 |
C6—C5—H5A | 120.0 | C15—C14—H14A | 119.8 |
C1—C6—C5 | 119.0 (2) | C10—C15—C14 | 120.1 (3) |
C1—C6—C7 | 124.2 (2) | C10—C15—H15A | 119.9 |
C5—C6—C7 | 116.8 (2) | C14—C15—H15A | 119.9 |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2A···O1 | 0.86 | 1.88 | 2.558 (3) | 134 |
N3—H3A···S1 | 0.86 | 2.59 | 2.923 (2) | 104 |
N1—H1A···O2i | 0.86 | 2.31 | 3.114 (3) | 155 |
C2—H2B···O1i | 0.93 | 2.47 | 3.263 (4) | 142 |
Symmetry code: (i) x, −y+1/2, z+1/2. |
Experimental details
Crystal data | |
Chemical formula | C15H13N3O2S |
Mr | 299.34 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 273 |
a, b, c (Å) | 14.7949 (19), 7.7004 (10), 13.9577 (18) |
β (°) | 117.705 (2) |
V (Å3) | 1407.8 (3) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.24 |
Crystal size (mm) | 0.55 × 0.21 × 0.10 |
Data collection | |
Diffractometer | Bruker SMART APEX CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.880, 0.977 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 7907, 3097, 1925 |
Rint | 0.043 |
(sin θ/λ)max (Å−1) | 0.650 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.057, 0.133, 1.05 |
No. of reflections | 3097 |
No. of parameters | 190 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.20, −0.19 |
Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SAINT, SHELXTL (Sheldrick, 1997), SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 1990).
S1—C8 | 1.659 (3) | N1—C8 | 1.388 (3) |
O1—C7 | 1.221 (3) | N2—C8 | 1.324 (3) |
O2—C9 | 1.222 (3) | N2—N3 | 1.375 (3) |
N1—C7 | 1.376 (3) | N3—C9 | 1.346 (3) |
C7—N1—C8 | 127.3 (2) | N2—C8—N1 | 115.4 (2) |
C9—N3—N2 | 119.8 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2A···O1 | 0.86 | 1.88 | 2.558 (3) | 134 |
N3—H3A···S1 | 0.86 | 2.59 | 2.923 (2) | 104 |
N1—H1A···O2i | 0.86 | 2.31 | 3.114 (3) | 155 |
C2—H2B···O1i | 0.93 | 2.47 | 3.263 (4) | 142 |
Symmetry code: (i) x, −y+1/2, z+1/2. |
The molecular structure and dimension of the title compound, (I), is similar to other benzoylthiourea derivatives, such as in N-benzoyl-N'-phenylthiourea (Yamin & Yusof, 2003a), N-benzoyl-N'-(3,4-dimethylphenyl)thiourea (Shanmuga Sundara Raj et al., 1999), N'-benzoyl-N-p-bromophenylthiourea (Yamin & Yusof, 2003b) with a cis–trans configuration with respect to the position of the benzamide and benzoyl groups relative to the S atom across the C8—N2 and C8—N1 bonds, respectively.
The central carbonyl–thiourea moiety (S1/C8/N1/N2) is planar. The benzoyl [maximum deviation at O1 of 0.348 (2) Å] and benzamide [maximum deviation at N3 of 0.306 (2) Å] fragments are essentially planar. The central thiourea moeity makes angles with the benzoyl and benzamide fragments of 15.12 (11) and 31.45 (12)°, respectively. The inclination between the benzoyl and benzamide fragments is 16.42 (14)°. There are two N—H···O and N—H···S intramolecular hydrogen bonds (Table 2). In the crystal structure, the molecules are linked by intermolecular N—H···O and C—H···O contacts (Table 2), forming linear chains parallel to the c axis (Fig. 2).