


Supporting information
![]() | Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536808009331/hb2717sup1.cif |
![]() | Structure factor file (CIF format) https://doi.org/10.1107/S1600536808009331/hb2717Isup2.hkl |
CCDC reference: 688925
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean
(C-C) = 0.004 Å
- R factor = 0.046
- wR factor = 0.104
- Data-to-parameter ratio = 13.1
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT230_ALERT_2_C Hirshfeld Test Diff for S1 - O2 .. 5.09 su PLAT318_ALERT_2_C Check Hybridisation of N1 in Main Residue . ?
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 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
1 mmol of 2-Acetyl-3-methylpyrazine (1 mmol) was added to a solution of benzenesulfonyl hydrazide (1 mmol) in 5 ml of 95% ethanol. The mixture was continuously stirred for 4 h at refluxing temperature, evaporating some ethanol, then, upon cooling, the solid product was collected by filtration and dried in vacuo (yield 67%). Clear blocks of (I) were obtained by evaporation from a methanol solution after 3 days.
The H atoms were placed geometrically (C—H = 0.93–0.96 Å, N—H = 0.86 Å) and refined as riding with Uiso(H) = 1.2Ueq(carrier) or 1.5Ueq(methyl C).
Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).
![]() | Fig. 1. The molecular structure of (I) showing 30% displacement ellipsoids for the non-hydrogen atoms. |
C13H14N4O2S | F(000) = 608 |
Mr = 290.34 | Dx = 1.409 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 1439 reflections |
a = 10.9848 (15) Å | θ = 3.0–22.9° |
b = 16.7921 (18) Å | µ = 0.24 mm−1 |
c = 7.4817 (10) Å | T = 298 K |
β = 97.264 (1)° | Block, colourless |
V = 1369.0 (3) Å3 | 0.50 × 0.28 × 0.14 mm |
Z = 4 |
Bruker SMART CCD diffractometer | 2402 independent reflections |
Radiation source: fine-focus sealed tube | 1499 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.061 |
ω scans | θmax = 25.0°, θmin = 1.9° |
Absorption correction: multi-scan (SADABS; Bruker, 2000) | h = −13→8 |
Tmin = 0.888, Tmax = 0.967 | k = −19→17 |
6807 measured reflections | l = −8→8 |
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)] = 0.046 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.103 | H-atom parameters constrained |
S = 1.03 | w = 1/[σ2(Fo2) + (0.036P)2] where P = (Fo2 + 2Fc2)/3 |
2402 reflections | (Δ/σ)max < 0.001 |
183 parameters | Δρmax = 0.32 e Å−3 |
0 restraints | Δρmin = −0.31 e Å−3 |
C13H14N4O2S | V = 1369.0 (3) Å3 |
Mr = 290.34 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 10.9848 (15) Å | µ = 0.24 mm−1 |
b = 16.7921 (18) Å | T = 298 K |
c = 7.4817 (10) Å | 0.50 × 0.28 × 0.14 mm |
β = 97.264 (1)° |
Bruker SMART CCD diffractometer | 2402 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2000) | 1499 reflections with I > 2σ(I) |
Tmin = 0.888, Tmax = 0.967 | Rint = 0.061 |
6807 measured reflections |
R[F2 > 2σ(F2)] = 0.046 | 0 restraints |
wR(F2) = 0.103 | H-atom parameters constrained |
S = 1.03 | Δρmax = 0.32 e Å−3 |
2402 reflections | Δρmin = −0.31 e Å−3 |
183 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 | ||
N1 | 0.76385 (18) | 0.24028 (12) | 0.7039 (3) | 0.0401 (6) | |
H1 | 0.7785 | 0.2885 | 0.7389 | 0.048* | |
N2 | 0.64583 (19) | 0.21106 (12) | 0.6591 (3) | 0.0386 (6) | |
N3 | 0.3511 (2) | 0.28276 (13) | 0.5461 (3) | 0.0504 (7) | |
N4 | 0.2852 (2) | 0.12465 (14) | 0.5560 (3) | 0.0552 (7) | |
O1 | 0.98156 (16) | 0.21805 (11) | 0.7451 (3) | 0.0528 (6) | |
O2 | 0.85153 (17) | 0.14561 (10) | 0.5061 (2) | 0.0508 (5) | |
S1 | 0.87236 (6) | 0.17593 (4) | 0.68486 (10) | 0.0412 (2) | |
C1 | 0.8548 (2) | 0.09773 (15) | 0.8320 (4) | 0.0385 (7) | |
C2 | 0.7922 (3) | 0.03023 (16) | 0.7692 (4) | 0.0539 (8) | |
H2 | 0.7631 | 0.0249 | 0.6475 | 0.065* | |
C3 | 0.7734 (3) | −0.02929 (19) | 0.8895 (6) | 0.0704 (10) | |
H3A | 0.7318 | −0.0754 | 0.8494 | 0.084* | |
C4 | 0.8160 (3) | −0.0204 (2) | 1.0670 (6) | 0.0723 (11) | |
H4 | 0.8010 | −0.0602 | 1.1479 | 0.087* | |
C5 | 0.8807 (3) | 0.0460 (2) | 1.1294 (4) | 0.0660 (10) | |
H5 | 0.9114 | 0.0505 | 1.2506 | 0.079* | |
C6 | 0.8996 (3) | 0.10584 (17) | 1.0104 (4) | 0.0516 (8) | |
H6 | 0.9425 | 0.1515 | 1.0508 | 0.062* | |
C7 | 0.5726 (3) | 0.34525 (15) | 0.7167 (4) | 0.0500 (8) | |
H7A | 0.6031 | 0.3497 | 0.8423 | 0.075* | |
H7B | 0.4948 | 0.3718 | 0.6935 | 0.075* | |
H7C | 0.6298 | 0.3694 | 0.6462 | 0.075* | |
C8 | 0.5571 (2) | 0.25952 (15) | 0.6673 (3) | 0.0361 (7) | |
C9 | 0.4326 (2) | 0.22753 (15) | 0.6112 (3) | 0.0370 (7) | |
C10 | 0.3985 (3) | 0.14763 (16) | 0.6207 (4) | 0.0427 (7) | |
C11 | 0.2074 (3) | 0.17989 (19) | 0.4865 (4) | 0.0581 (9) | |
H11 | 0.1286 | 0.1650 | 0.4380 | 0.070* | |
C12 | 0.2400 (3) | 0.2581 (2) | 0.4845 (4) | 0.0588 (9) | |
H12 | 0.1817 | 0.2953 | 0.4381 | 0.071* | |
C13 | 0.4793 (3) | 0.08310 (16) | 0.7054 (4) | 0.0641 (10) | |
H13A | 0.4296 | 0.0395 | 0.7368 | 0.096* | |
H13B | 0.5272 | 0.1031 | 0.8121 | 0.096* | |
H13C | 0.5329 | 0.0651 | 0.6220 | 0.096* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0289 (14) | 0.0326 (12) | 0.0566 (16) | −0.0015 (10) | −0.0026 (11) | −0.0017 (11) |
N2 | 0.0279 (14) | 0.0445 (13) | 0.0413 (15) | −0.0002 (11) | −0.0037 (11) | −0.0015 (11) |
N3 | 0.0346 (16) | 0.0528 (15) | 0.0610 (18) | 0.0029 (12) | −0.0043 (13) | 0.0027 (13) |
N4 | 0.0402 (17) | 0.0594 (16) | 0.0645 (18) | −0.0082 (13) | 0.0006 (13) | −0.0014 (14) |
O1 | 0.0291 (12) | 0.0601 (13) | 0.0667 (14) | −0.0069 (9) | −0.0033 (10) | 0.0065 (11) |
O2 | 0.0515 (13) | 0.0615 (13) | 0.0383 (12) | 0.0083 (10) | 0.0008 (9) | −0.0039 (10) |
S1 | 0.0308 (4) | 0.0479 (4) | 0.0439 (5) | 0.0027 (3) | 0.0003 (3) | 0.0018 (4) |
C1 | 0.0321 (17) | 0.0405 (16) | 0.0429 (19) | 0.0085 (12) | 0.0042 (13) | −0.0010 (14) |
C2 | 0.044 (2) | 0.0517 (19) | 0.063 (2) | 0.0042 (15) | −0.0036 (16) | 0.0007 (18) |
C3 | 0.065 (2) | 0.049 (2) | 0.096 (3) | −0.0003 (16) | 0.007 (2) | 0.013 (2) |
C4 | 0.080 (3) | 0.057 (2) | 0.086 (3) | 0.019 (2) | 0.037 (2) | 0.025 (2) |
C5 | 0.085 (3) | 0.069 (2) | 0.047 (2) | 0.034 (2) | 0.0166 (19) | 0.004 (2) |
C6 | 0.061 (2) | 0.0464 (18) | 0.048 (2) | 0.0134 (15) | 0.0079 (16) | −0.0043 (16) |
C7 | 0.0441 (19) | 0.0471 (18) | 0.056 (2) | 0.0026 (13) | −0.0027 (15) | −0.0038 (15) |
C8 | 0.0340 (17) | 0.0413 (16) | 0.0323 (17) | 0.0031 (13) | 0.0014 (13) | 0.0011 (13) |
C9 | 0.0316 (17) | 0.0447 (17) | 0.0342 (17) | 0.0030 (13) | 0.0019 (13) | −0.0008 (14) |
C10 | 0.0374 (18) | 0.0484 (17) | 0.0422 (18) | −0.0012 (14) | 0.0045 (14) | −0.0009 (15) |
C11 | 0.0324 (19) | 0.073 (2) | 0.066 (2) | −0.0047 (17) | −0.0047 (16) | −0.0056 (19) |
C12 | 0.032 (2) | 0.069 (2) | 0.071 (2) | 0.0059 (16) | −0.0084 (16) | 0.0003 (18) |
C13 | 0.050 (2) | 0.0490 (19) | 0.090 (3) | −0.0034 (15) | −0.0032 (18) | 0.0134 (19) |
N1—N2 | 1.387 (3) | C4—H4 | 0.9300 |
N1—S1 | 1.628 (2) | C5—C6 | 1.376 (4) |
N1—H1 | 0.8600 | C5—H5 | 0.9300 |
N2—C8 | 1.277 (3) | C6—H6 | 0.9300 |
N3—C12 | 1.316 (3) | C7—C8 | 1.491 (3) |
N3—C9 | 1.337 (3) | C7—H7A | 0.9600 |
N4—C11 | 1.323 (3) | C7—H7B | 0.9600 |
N4—C10 | 1.334 (3) | C7—H7C | 0.9600 |
O1—S1 | 1.4163 (18) | C8—C9 | 1.480 (3) |
O2—S1 | 1.4220 (19) | C9—C10 | 1.397 (3) |
S1—C1 | 1.740 (3) | C10—C13 | 1.490 (3) |
C1—C6 | 1.370 (4) | C11—C12 | 1.361 (4) |
C1—C2 | 1.377 (3) | C11—H11 | 0.9300 |
C2—C3 | 1.378 (4) | C12—H12 | 0.9300 |
C2—H2 | 0.9300 | C13—H13A | 0.9600 |
C3—C4 | 1.359 (5) | C13—H13B | 0.9600 |
C3—H3A | 0.9300 | C13—H13C | 0.9600 |
C4—C5 | 1.372 (4) | ||
N2—N1—S1 | 114.60 (16) | C5—C6—H6 | 120.2 |
N2—N1—H1 | 122.7 | C8—C7—H7A | 109.5 |
S1—N1—H1 | 122.7 | C8—C7—H7B | 109.5 |
C8—N2—N1 | 117.3 (2) | H7A—C7—H7B | 109.5 |
C12—N3—C9 | 117.2 (2) | C8—C7—H7C | 109.5 |
C11—N4—C10 | 117.8 (3) | H7A—C7—H7C | 109.5 |
O1—S1—O2 | 120.49 (13) | H7B—C7—H7C | 109.5 |
O1—S1—N1 | 103.92 (12) | N2—C8—C9 | 116.0 (2) |
O2—S1—N1 | 106.70 (11) | N2—C8—C7 | 124.3 (2) |
O1—S1—C1 | 109.44 (12) | C9—C8—C7 | 119.5 (2) |
O2—S1—C1 | 107.89 (12) | N3—C9—C10 | 120.9 (2) |
N1—S1—C1 | 107.71 (12) | N3—C9—C8 | 113.8 (2) |
C6—C1—C2 | 121.1 (3) | C10—C9—C8 | 125.3 (2) |
C6—C1—S1 | 119.1 (2) | N4—C10—C9 | 120.2 (2) |
C2—C1—S1 | 119.7 (2) | N4—C10—C13 | 115.0 (2) |
C1—C2—C3 | 118.9 (3) | C9—C10—C13 | 124.8 (2) |
C1—C2—H2 | 120.6 | N4—C11—C12 | 121.5 (3) |
C3—C2—H2 | 120.6 | N4—C11—H11 | 119.2 |
C4—C3—C2 | 119.8 (3) | C12—C11—H11 | 119.2 |
C4—C3—H3A | 120.1 | N3—C12—C11 | 122.3 (3) |
C2—C3—H3A | 120.1 | N3—C12—H12 | 118.9 |
C3—C4—C5 | 121.4 (3) | C11—C12—H12 | 118.9 |
C3—C4—H4 | 119.3 | C10—C13—H13A | 109.5 |
C5—C4—H4 | 119.3 | C10—C13—H13B | 109.5 |
C4—C5—C6 | 119.2 (3) | H13A—C13—H13B | 109.5 |
C4—C5—H5 | 120.4 | C10—C13—H13C | 109.5 |
C6—C5—H5 | 120.4 | H13A—C13—H13C | 109.5 |
C1—C6—C5 | 119.5 (3) | H13B—C13—H13C | 109.5 |
C1—C6—H6 | 120.2 | ||
S1—N1—N2—C8 | −178.3 (2) | N1—N2—C8—C9 | 177.5 (2) |
N2—N1—S1—O1 | −177.34 (18) | N1—N2—C8—C7 | 1.7 (4) |
N2—N1—S1—O2 | 54.3 (2) | C12—N3—C9—C10 | −2.9 (4) |
N2—N1—S1—C1 | −61.3 (2) | C12—N3—C9—C8 | 176.5 (3) |
O1—S1—C1—C6 | 30.8 (3) | N2—C8—C9—N3 | −152.2 (3) |
O2—S1—C1—C6 | 163.6 (2) | C7—C8—C9—N3 | 23.8 (4) |
N1—S1—C1—C6 | −81.6 (2) | N2—C8—C9—C10 | 27.2 (4) |
O1—S1—C1—C2 | −151.7 (2) | C7—C8—C9—C10 | −156.8 (3) |
O2—S1—C1—C2 | −18.9 (3) | C11—N4—C10—C9 | −1.1 (4) |
N1—S1—C1—C2 | 96.0 (2) | C11—N4—C10—C13 | 177.0 (3) |
C6—C1—C2—C3 | 0.9 (4) | N3—C9—C10—N4 | 3.5 (4) |
S1—C1—C2—C3 | −176.5 (2) | C8—C9—C10—N4 | −175.9 (3) |
C1—C2—C3—C4 | 0.3 (5) | N3—C9—C10—C13 | −174.4 (3) |
C2—C3—C4—C5 | −1.8 (5) | C8—C9—C10—C13 | 6.3 (5) |
C3—C4—C5—C6 | 2.0 (5) | C10—N4—C11—C12 | −1.6 (5) |
C2—C1—C6—C5 | −0.7 (4) | C9—N3—C12—C11 | 0.2 (5) |
S1—C1—C6—C5 | 176.8 (2) | N4—C11—C12—N3 | 2.1 (5) |
C4—C5—C6—C1 | −0.7 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O2i | 0.86 | 2.34 | 3.027 (3) | 137 |
Symmetry code: (i) x, −y+1/2, z+1/2. |
Experimental details
Crystal data | |
Chemical formula | C13H14N4O2S |
Mr | 290.34 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 298 |
a, b, c (Å) | 10.9848 (15), 16.7921 (18), 7.4817 (10) |
β (°) | 97.264 (1) |
V (Å3) | 1369.0 (3) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.24 |
Crystal size (mm) | 0.50 × 0.28 × 0.14 |
Data collection | |
Diffractometer | Bruker SMART CCD diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 2000) |
Tmin, Tmax | 0.888, 0.967 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 6807, 2402, 1499 |
Rint | 0.061 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.046, 0.103, 1.03 |
No. of reflections | 2402 |
No. of parameters | 183 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.32, −0.31 |
Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O2i | 0.86 | 2.34 | 3.027 (3) | 137 |
Symmetry code: (i) x, −y+1/2, z+1/2. |
As part of our ongoing studies of aroylhydrazones as possible ligands (Tai et al., 2008), we now report the synthesis and structure of the title compound, (I), (Fig. 1).
The dihedral angle between the aromatic ring planes is 55.42 (14)°. Otherwise, the geometrical parameters for (I) are normal. In the crystal of (I), an N-H···O hydrogen bond (Table 1) leads to [001] chains.