organic compounds
Benzyl 3-[(E)-1-(pyrazin-2-yl)ethylidene]dithiocarbazate
aCollege of Chemical Engineering and Materials Science, Zhejiang University of Technology, People's Republic of China
*Correspondence e-mail: shanshang@mail.hz.zj.cn
The title compound, C14H14N4S2, was obtained from a condensation reaction of benzyl dithiocarbazate and acetylpyrazine. The contains two independent molecules, in each of which the pyrazine ring and dithiocarbazate unit are approximately co-planar, the r.m.s. deviations being 0.0304 and 0.0418 Å. The mean plane is oriented with respect to the benzene ring at 49.22 (4)° in one molecule and at 69.76 (7)° in the other. In the crystal, the molecules are linked to each other via intermolecular N—H⋯S hydrogen bonds, forming centrosymmetric supramolecular dimers.
Related literature
For applications of hydrazone and its derivatives in the biological field, see: Okabe et al. (1993); Hu et al. (2001). For related structures, see: Shan et al. (2006, 2008a,b). For the synthesis, see: Hu et al. (2001).
Experimental
Crystal data
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Refinement
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Data collection: PROCESS-AUTO (Rigaku, 1998); cell PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).
Supporting information
10.1107/S1600536811028480/xu5267sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536811028480/xu5267Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536811028480/xu5267Isup3.cml
Benzyl dithiocarbazate was synthesized as described previously (Hu et al., 2001). Benzyl dithiocarbazate (0.4 g, 2 mmol) and acetylpyrazine (0.24 g, 2 mmol) were dissolved in ethanol (20 ml), then acetic acid (0.2 ml) was added to the ethanol solution with stirring. The mixture solution was refluxed for 6 h. After cooling to room temperature, yellow microcrystals appeared. The microcrystals were separated from the solution and washed with cold water three times. Recrystallization was performed twice with absolute methanol to obtain single crystals of the title compound.
H atoms were placed in calculated positions with C—H = 0.93 (aromatic), 0.97 (methylene) and N—H = 0.86 Å, and refined in riding mode with Uiso(H) = 1.2Ueq(C,N).
Data collection: PROCESS-AUTO (Rigaku, 1998); cell
PROCESS-AUTO (Rigaku, 1998); data reduction: CrystalStructure (Rigaku/MSC, 2002); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).Fig. 1. The molecular structure of the title compound with 40% probability displacement (arbitrary spheres for H atoms). |
C14H14N4S2 | Z = 4 |
Mr = 302.41 | F(000) = 632 |
Triclinic, P1 | Dx = 1.375 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 9.511 (3) Å | Cell parameters from 5249 reflections |
b = 9.786 (3) Å | θ = 3.3–25.2° |
c = 17.144 (5) Å | µ = 0.36 mm−1 |
α = 90.688 (4)° | T = 294 K |
β = 100.178 (6)° | Needle, yellow |
γ = 111.006 (6)° | 0.45 × 0.23 × 0.22 mm |
V = 1461.2 (8) Å3 |
Rigaku R-AXIS RAPID IP diffractometer | 5249 independent reflections |
Radiation source: fine-focus sealed tube | 3005 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.027 |
Detector resolution: 10.0 pixels mm-1 | θmax = 25.2°, θmin = 3.4° |
ω scans | h = −11→10 |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | k = −10→11 |
Tmin = 0.88, Tmax = 0.90 | l = −17→20 |
9171 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)] = 0.044 | H-atom parameters constrained |
wR(F2) = 0.111 | w = 1/[σ2(Fo2) + (0.0442P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.94 | (Δ/σ)max < 0.001 |
5249 reflections | Δρmax = 0.21 e Å−3 |
364 parameters | Δρmin = −0.22 e Å−3 |
0 restraints | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0051 (7) |
C14H14N4S2 | γ = 111.006 (6)° |
Mr = 302.41 | V = 1461.2 (8) Å3 |
Triclinic, P1 | Z = 4 |
a = 9.511 (3) Å | Mo Kα radiation |
b = 9.786 (3) Å | µ = 0.36 mm−1 |
c = 17.144 (5) Å | T = 294 K |
α = 90.688 (4)° | 0.45 × 0.23 × 0.22 mm |
β = 100.178 (6)° |
Rigaku R-AXIS RAPID IP diffractometer | 5249 independent reflections |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | 3005 reflections with I > 2σ(I) |
Tmin = 0.88, Tmax = 0.90 | Rint = 0.027 |
9171 measured reflections |
R[F2 > 2σ(F2)] = 0.044 | 0 restraints |
wR(F2) = 0.111 | H-atom parameters constrained |
S = 0.94 | Δρmax = 0.21 e Å−3 |
5249 reflections | Δρmin = −0.22 e Å−3 |
364 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 | ||
S1 | 0.37949 (8) | 0.30497 (8) | 0.39964 (4) | 0.0577 (2) | |
S2 | 0.47351 (8) | 0.22593 (7) | 0.25099 (4) | 0.0478 (2) | |
S3 | 0.36950 (8) | 0.79605 (8) | 0.39238 (4) | 0.0576 (2) | |
S4 | 0.47142 (8) | 0.73081 (7) | 0.24347 (4) | 0.0475 (2) | |
N1 | 0.9596 (3) | −0.0100 (2) | 0.37093 (13) | 0.0612 (6) | |
N2 | 0.9043 (3) | 0.0108 (3) | 0.20740 (14) | 0.0678 (7) | |
N3 | 0.6706 (2) | 0.1393 (2) | 0.35110 (11) | 0.0440 (5) | |
N4 | 0.5883 (2) | 0.1903 (2) | 0.39383 (12) | 0.0462 (5) | |
H4N | 0.6029 | 0.1905 | 0.4448 | 0.055* | |
N5 | 0.9564 (3) | 0.4878 (2) | 0.37052 (13) | 0.0579 (6) | |
N6 | 0.9118 (3) | 0.5081 (3) | 0.20683 (14) | 0.0700 (7) | |
N7 | 0.6718 (2) | 0.6436 (2) | 0.34506 (12) | 0.0451 (5) | |
N8 | 0.5870 (2) | 0.6937 (2) | 0.38655 (12) | 0.0475 (5) | |
H8N | 0.6022 | 0.6962 | 0.4376 | 0.057* | |
C1 | 0.8542 (3) | 0.0416 (2) | 0.33694 (14) | 0.0419 (6) | |
C2 | 0.8283 (3) | 0.0504 (3) | 0.25545 (16) | 0.0575 (7) | |
H2 | 0.7532 | 0.0862 | 0.2331 | 0.069* | |
C3 | 1.0097 (3) | −0.0394 (3) | 0.24298 (18) | 0.0623 (8) | |
H3 | 1.0675 | −0.0680 | 0.2124 | 0.075* | |
C4 | 1.0353 (3) | −0.0503 (3) | 0.32220 (18) | 0.0664 (8) | |
H4 | 1.1094 | −0.0878 | 0.3439 | 0.080* | |
C5 | 0.7692 (3) | 0.0897 (2) | 0.38862 (14) | 0.0421 (6) | |
C6 | 0.8013 (3) | 0.0798 (3) | 0.47576 (15) | 0.0646 (8) | |
H6A | 0.8297 | 0.1752 | 0.5026 | 0.097* | |
H6B | 0.8838 | 0.0445 | 0.4894 | 0.097* | |
H6C | 0.7110 | 0.0132 | 0.4917 | 0.097* | |
C7 | 0.4838 (3) | 0.2402 (2) | 0.35357 (14) | 0.0420 (6) | |
C8 | 0.3348 (3) | 0.3081 (3) | 0.21370 (14) | 0.0513 (7) | |
H8A | 0.2407 | 0.2609 | 0.2333 | 0.062* | |
H8B | 0.3751 | 0.4118 | 0.2314 | 0.062* | |
C9 | 0.3036 (3) | 0.2880 (2) | 0.12422 (15) | 0.0443 (6) | |
C10 | 0.1556 (3) | 0.2220 (3) | 0.08232 (16) | 0.0591 (8) | |
H10 | 0.0749 | 0.1883 | 0.1095 | 0.071* | |
C11 | 0.1261 (4) | 0.2054 (3) | 0.00069 (19) | 0.0731 (9) | |
H11 | 0.0254 | 0.1628 | −0.0270 | 0.088* | |
C12 | 0.2447 (4) | 0.2513 (3) | −0.04033 (18) | 0.0697 (9) | |
H12 | 0.2246 | 0.2382 | −0.0956 | 0.084* | |
C13 | 0.3914 (4) | 0.3160 (3) | 0.00040 (18) | 0.0670 (8) | |
H13 | 0.4720 | 0.3470 | −0.0271 | 0.080* | |
C14 | 0.4215 (3) | 0.3359 (3) | 0.08218 (17) | 0.0590 (8) | |
H14 | 0.5221 | 0.3819 | 0.1094 | 0.071* | |
C15 | 0.8569 (3) | 0.5450 (2) | 0.33416 (14) | 0.0401 (6) | |
C16 | 0.8372 (3) | 0.5543 (3) | 0.25265 (15) | 0.0568 (7) | |
H16 | 0.7676 | 0.5954 | 0.2289 | 0.068* | |
C17 | 1.0091 (3) | 0.4506 (3) | 0.24458 (18) | 0.0620 (8) | |
H17 | 1.0642 | 0.4153 | 0.2153 | 0.074* | |
C18 | 1.0308 (3) | 0.4415 (3) | 0.32380 (18) | 0.0623 (8) | |
H18 | 1.1013 | 0.4010 | 0.3470 | 0.075* | |
C19 | 0.7713 (3) | 0.5969 (2) | 0.38395 (14) | 0.0430 (6) | |
C20 | 0.8037 (3) | 0.5919 (3) | 0.47198 (15) | 0.0620 (8) | |
H20A | 0.8294 | 0.6881 | 0.4972 | 0.093* | |
H20B | 0.8882 | 0.5596 | 0.4869 | 0.093* | |
H20C | 0.7145 | 0.5247 | 0.4884 | 0.093* | |
C21 | 0.4789 (3) | 0.7394 (2) | 0.34580 (14) | 0.0416 (6) | |
C22 | 0.3174 (3) | 0.7955 (3) | 0.20720 (14) | 0.0487 (7) | |
H22A | 0.2249 | 0.7366 | 0.2254 | 0.058* | |
H22B | 0.3457 | 0.8969 | 0.2271 | 0.058* | |
C23 | 0.2895 (3) | 0.7829 (3) | 0.11759 (14) | 0.0428 (6) | |
C24 | 0.2221 (3) | 0.6467 (3) | 0.07488 (16) | 0.0533 (7) | |
H24 | 0.1938 | 0.5621 | 0.1018 | 0.064* | |
C25 | 0.1965 (3) | 0.6353 (3) | −0.00675 (17) | 0.0605 (8) | |
H25 | 0.1516 | 0.5432 | −0.0347 | 0.073* | |
C26 | 0.2366 (3) | 0.7584 (3) | −0.04698 (16) | 0.0632 (8) | |
H26 | 0.2194 | 0.7505 | −0.1022 | 0.076* | |
C27 | 0.3021 (4) | 0.8932 (3) | −0.00586 (17) | 0.0677 (8) | |
H27 | 0.3283 | 0.9775 | −0.0331 | 0.081* | |
C28 | 0.3295 (3) | 0.9046 (3) | 0.07592 (17) | 0.0599 (8) | |
H28 | 0.3761 | 0.9970 | 0.1034 | 0.072* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0636 (5) | 0.0886 (5) | 0.0419 (4) | 0.0505 (4) | 0.0153 (4) | 0.0049 (4) |
S2 | 0.0585 (5) | 0.0617 (4) | 0.0362 (4) | 0.0382 (3) | 0.0076 (3) | 0.0020 (3) |
S3 | 0.0596 (5) | 0.0915 (5) | 0.0420 (4) | 0.0499 (4) | 0.0142 (3) | 0.0052 (4) |
S4 | 0.0525 (4) | 0.0643 (4) | 0.0365 (4) | 0.0341 (3) | 0.0091 (3) | 0.0026 (3) |
N1 | 0.0642 (16) | 0.0921 (16) | 0.0485 (14) | 0.0546 (14) | 0.0094 (12) | 0.0079 (12) |
N2 | 0.0755 (18) | 0.1014 (18) | 0.0466 (15) | 0.0511 (15) | 0.0225 (13) | 0.0082 (13) |
N3 | 0.0461 (13) | 0.0598 (12) | 0.0379 (12) | 0.0323 (11) | 0.0103 (10) | 0.0047 (10) |
N4 | 0.0507 (13) | 0.0675 (13) | 0.0327 (11) | 0.0351 (11) | 0.0105 (10) | 0.0069 (10) |
N5 | 0.0585 (15) | 0.0868 (15) | 0.0464 (14) | 0.0465 (13) | 0.0135 (12) | 0.0071 (12) |
N6 | 0.0879 (19) | 0.0954 (17) | 0.0469 (15) | 0.0527 (16) | 0.0235 (14) | 0.0005 (13) |
N7 | 0.0465 (13) | 0.0607 (12) | 0.0394 (12) | 0.0327 (11) | 0.0092 (10) | 0.0033 (10) |
N8 | 0.0505 (13) | 0.0693 (13) | 0.0345 (12) | 0.0355 (11) | 0.0090 (10) | 0.0047 (10) |
C1 | 0.0427 (15) | 0.0487 (13) | 0.0382 (15) | 0.0213 (12) | 0.0080 (12) | 0.0037 (11) |
C2 | 0.065 (2) | 0.0804 (18) | 0.0451 (17) | 0.0451 (16) | 0.0155 (15) | 0.0124 (14) |
C3 | 0.062 (2) | 0.0807 (19) | 0.059 (2) | 0.0377 (16) | 0.0260 (16) | 0.0021 (16) |
C4 | 0.064 (2) | 0.095 (2) | 0.063 (2) | 0.0555 (17) | 0.0150 (17) | 0.0080 (17) |
C5 | 0.0412 (15) | 0.0532 (14) | 0.0360 (14) | 0.0225 (12) | 0.0064 (12) | 0.0055 (11) |
C6 | 0.069 (2) | 0.107 (2) | 0.0379 (16) | 0.0568 (17) | 0.0089 (14) | 0.0074 (15) |
C7 | 0.0450 (15) | 0.0468 (13) | 0.0385 (14) | 0.0217 (12) | 0.0088 (12) | 0.0036 (11) |
C8 | 0.0585 (17) | 0.0630 (15) | 0.0456 (16) | 0.0384 (14) | 0.0090 (13) | 0.0040 (12) |
C9 | 0.0510 (17) | 0.0437 (14) | 0.0449 (16) | 0.0264 (12) | 0.0065 (13) | 0.0077 (12) |
C10 | 0.0509 (18) | 0.0758 (18) | 0.0556 (19) | 0.0294 (15) | 0.0090 (15) | 0.0125 (15) |
C11 | 0.062 (2) | 0.088 (2) | 0.058 (2) | 0.0224 (17) | −0.0059 (18) | 0.0055 (17) |
C12 | 0.090 (3) | 0.077 (2) | 0.0420 (18) | 0.0338 (18) | 0.0051 (18) | 0.0095 (15) |
C13 | 0.069 (2) | 0.0793 (19) | 0.056 (2) | 0.0275 (17) | 0.0208 (17) | 0.0164 (16) |
C14 | 0.0530 (18) | 0.0644 (17) | 0.0540 (19) | 0.0167 (14) | 0.0058 (15) | 0.0106 (14) |
C15 | 0.0398 (15) | 0.0486 (13) | 0.0346 (14) | 0.0195 (12) | 0.0067 (12) | 0.0027 (11) |
C16 | 0.066 (2) | 0.0785 (18) | 0.0397 (16) | 0.0432 (16) | 0.0096 (14) | 0.0060 (14) |
C17 | 0.068 (2) | 0.0739 (18) | 0.062 (2) | 0.0402 (16) | 0.0272 (16) | 0.0011 (15) |
C18 | 0.063 (2) | 0.090 (2) | 0.0549 (19) | 0.0510 (17) | 0.0162 (15) | 0.0061 (16) |
C19 | 0.0440 (16) | 0.0530 (14) | 0.0381 (15) | 0.0243 (12) | 0.0092 (12) | 0.0046 (11) |
C20 | 0.0646 (19) | 0.101 (2) | 0.0391 (16) | 0.0539 (17) | 0.0077 (14) | 0.0021 (14) |
C21 | 0.0421 (15) | 0.0479 (13) | 0.0388 (14) | 0.0217 (11) | 0.0071 (12) | 0.0020 (11) |
C22 | 0.0529 (17) | 0.0579 (15) | 0.0446 (16) | 0.0318 (13) | 0.0081 (13) | 0.0048 (12) |
C23 | 0.0401 (15) | 0.0526 (15) | 0.0421 (15) | 0.0252 (12) | 0.0065 (12) | 0.0051 (12) |
C24 | 0.0583 (18) | 0.0520 (16) | 0.0512 (18) | 0.0229 (13) | 0.0085 (14) | 0.0069 (13) |
C25 | 0.0604 (19) | 0.0646 (18) | 0.0541 (19) | 0.0246 (15) | 0.0020 (15) | −0.0082 (15) |
C26 | 0.071 (2) | 0.086 (2) | 0.0405 (17) | 0.0403 (17) | 0.0041 (15) | 0.0041 (16) |
C27 | 0.085 (2) | 0.0684 (19) | 0.055 (2) | 0.0332 (16) | 0.0161 (17) | 0.0223 (16) |
C28 | 0.073 (2) | 0.0510 (15) | 0.0564 (19) | 0.0264 (14) | 0.0073 (15) | 0.0055 (14) |
S1—C7 | 1.651 (2) | C9—C10 | 1.376 (3) |
S2—C7 | 1.745 (2) | C9—C14 | 1.383 (4) |
S2—C8 | 1.808 (2) | C10—C11 | 1.374 (4) |
S3—C21 | 1.650 (2) | C10—H10 | 0.9300 |
S4—C21 | 1.743 (3) | C11—C12 | 1.376 (4) |
S4—C22 | 1.813 (2) | C11—H11 | 0.9300 |
N1—C1 | 1.327 (3) | C12—C13 | 1.360 (4) |
N1—C4 | 1.335 (3) | C12—H12 | 0.9300 |
N2—C2 | 1.325 (3) | C13—C14 | 1.377 (4) |
N2—C3 | 1.327 (3) | C13—H13 | 0.9300 |
N3—C5 | 1.284 (3) | C14—H14 | 0.9300 |
N3—N4 | 1.368 (3) | C15—C16 | 1.385 (3) |
N4—C7 | 1.348 (3) | C15—C19 | 1.477 (3) |
N4—H4N | 0.8600 | C16—H16 | 0.9300 |
N5—C18 | 1.330 (3) | C17—C18 | 1.346 (4) |
N5—C15 | 1.333 (3) | C17—H17 | 0.9300 |
N6—C16 | 1.321 (3) | C18—H18 | 0.9300 |
N6—C17 | 1.328 (3) | C19—C20 | 1.491 (3) |
N7—C19 | 1.282 (3) | C20—H20A | 0.9600 |
N7—N8 | 1.370 (3) | C20—H20B | 0.9600 |
N8—C21 | 1.352 (3) | C20—H20C | 0.9600 |
N8—H8N | 0.8600 | C22—C23 | 1.508 (3) |
C1—C2 | 1.384 (3) | C22—H22A | 0.9700 |
C1—C5 | 1.475 (3) | C22—H22B | 0.9700 |
C2—H2 | 0.9300 | C23—C28 | 1.366 (3) |
C3—C4 | 1.349 (4) | C23—C24 | 1.386 (3) |
C3—H3 | 0.9300 | C24—C25 | 1.374 (4) |
C4—H4 | 0.9300 | C24—H24 | 0.9300 |
C5—C6 | 1.482 (3) | C25—C26 | 1.362 (4) |
C6—H6A | 0.9600 | C25—H25 | 0.9300 |
C6—H6B | 0.9600 | C26—C27 | 1.363 (3) |
C6—H6C | 0.9600 | C26—H26 | 0.9300 |
C8—C9 | 1.507 (3) | C27—C28 | 1.376 (4) |
C8—H8A | 0.9700 | C27—H27 | 0.9300 |
C8—H8B | 0.9700 | C28—H28 | 0.9300 |
C7—S2—C8 | 102.79 (11) | C11—C12—H12 | 120.2 |
C21—S4—C22 | 102.13 (11) | C12—C13—C14 | 120.3 (3) |
C1—N1—C4 | 116.0 (2) | C12—C13—H13 | 119.8 |
C2—N2—C3 | 115.1 (3) | C14—C13—H13 | 119.8 |
C5—N3—N4 | 118.6 (2) | C13—C14—C9 | 120.7 (3) |
C7—N4—N3 | 117.9 (2) | C13—C14—H14 | 119.7 |
C7—N4—H4N | 121.0 | C9—C14—H14 | 119.7 |
N3—N4—H4N | 121.0 | N5—C15—C16 | 120.0 (2) |
C18—N5—C15 | 115.9 (2) | N5—C15—C19 | 117.5 (2) |
C16—N6—C17 | 115.0 (3) | C16—C15—C19 | 122.4 (2) |
C19—N7—N8 | 118.4 (2) | N6—C16—C15 | 123.6 (3) |
C21—N8—N7 | 118.8 (2) | N6—C16—H16 | 118.2 |
C21—N8—H8N | 120.6 | C15—C16—H16 | 118.2 |
N7—N8—H8N | 120.6 | N6—C17—C18 | 122.3 (3) |
N1—C1—C2 | 119.9 (2) | N6—C17—H17 | 118.8 |
N1—C1—C5 | 118.0 (2) | C18—C17—H17 | 118.8 |
C2—C1—C5 | 122.1 (2) | N5—C18—C17 | 123.2 (3) |
N2—C2—C1 | 123.7 (3) | N5—C18—H18 | 118.4 |
N2—C2—H2 | 118.1 | C17—C18—H18 | 118.4 |
C1—C2—H2 | 118.1 | N7—C19—C15 | 114.5 (2) |
N2—C3—C4 | 122.0 (3) | N7—C19—C20 | 125.4 (2) |
N2—C3—H3 | 119.0 | C15—C19—C20 | 120.1 (2) |
C4—C3—H3 | 119.0 | C19—C20—H20A | 109.5 |
N1—C4—C3 | 123.2 (3) | C19—C20—H20B | 109.5 |
N1—C4—H4 | 118.4 | H20A—C20—H20B | 109.5 |
C3—C4—H4 | 118.4 | C19—C20—H20C | 109.5 |
N3—C5—C1 | 113.9 (2) | H20A—C20—H20C | 109.5 |
N3—C5—C6 | 125.6 (2) | H20B—C20—H20C | 109.5 |
C1—C5—C6 | 120.5 (2) | N8—C21—S3 | 120.95 (19) |
C5—C6—H6A | 109.5 | N8—C21—S4 | 113.05 (18) |
C5—C6—H6B | 109.5 | S3—C21—S4 | 126.01 (14) |
H6A—C6—H6B | 109.5 | C23—C22—S4 | 108.01 (16) |
C5—C6—H6C | 109.5 | C23—C22—H22A | 110.1 |
H6A—C6—H6C | 109.5 | S4—C22—H22A | 110.1 |
H6B—C6—H6C | 109.5 | C23—C22—H22B | 110.1 |
N4—C7—S1 | 121.67 (19) | S4—C22—H22B | 110.1 |
N4—C7—S2 | 112.47 (18) | H22A—C22—H22B | 108.4 |
S1—C7—S2 | 125.85 (14) | C28—C23—C24 | 117.9 (2) |
C9—C8—S2 | 107.72 (16) | C28—C23—C22 | 121.3 (2) |
C9—C8—H8A | 110.2 | C24—C23—C22 | 120.8 (2) |
S2—C8—H8A | 110.2 | C25—C24—C23 | 120.8 (2) |
C9—C8—H8B | 110.2 | C25—C24—H24 | 119.6 |
S2—C8—H8B | 110.2 | C23—C24—H24 | 119.6 |
H8A—C8—H8B | 108.5 | C26—C25—C24 | 120.2 (2) |
C10—C9—C14 | 118.4 (2) | C26—C25—H25 | 119.9 |
C10—C9—C8 | 120.3 (3) | C24—C25—H25 | 119.9 |
C14—C9—C8 | 121.3 (2) | C25—C26—C27 | 119.7 (3) |
C11—C10—C9 | 120.6 (3) | C25—C26—H26 | 120.1 |
C11—C10—H10 | 119.7 | C27—C26—H26 | 120.1 |
C9—C10—H10 | 119.7 | C26—C27—C28 | 120.1 (3) |
C10—C11—C12 | 120.4 (3) | C26—C27—H27 | 120.0 |
C10—C11—H11 | 119.8 | C28—C27—H27 | 120.0 |
C12—C11—H11 | 119.8 | C23—C28—C27 | 121.3 (2) |
C13—C12—C11 | 119.6 (3) | C23—C28—H28 | 119.3 |
C13—C12—H12 | 120.2 | C27—C28—H28 | 119.3 |
D—H···A | D—H | H···A | D···A | D—H···A |
N4—H4N···S3i | 0.86 | 2.75 | 3.611 (2) | 175 |
N8—H8N···S1i | 0.86 | 2.77 | 3.622 (2) | 174 |
Symmetry code: (i) −x+1, −y+1, −z+1. |
Experimental details
Crystal data | |
Chemical formula | C14H14N4S2 |
Mr | 302.41 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 294 |
a, b, c (Å) | 9.511 (3), 9.786 (3), 17.144 (5) |
α, β, γ (°) | 90.688 (4), 100.178 (6), 111.006 (6) |
V (Å3) | 1461.2 (8) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.36 |
Crystal size (mm) | 0.45 × 0.23 × 0.22 |
Data collection | |
Diffractometer | Rigaku R-AXIS RAPID IP diffractometer |
Absorption correction | Multi-scan (ABSCOR; Higashi, 1995) |
Tmin, Tmax | 0.88, 0.90 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 9171, 5249, 3005 |
Rint | 0.027 |
(sin θ/λ)max (Å−1) | 0.599 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.044, 0.111, 0.94 |
No. of reflections | 5249 |
No. of parameters | 364 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.21, −0.22 |
Computer programs: PROCESS-AUTO (Rigaku, 1998), CrystalStructure (Rigaku/MSC, 2002), SIR92 (Altomare et al., 1993), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).
D—H···A | D—H | H···A | D···A | D—H···A |
N4—H4N···S3i | 0.86 | 2.75 | 3.611 (2) | 175 |
N8—H8N···S1i | 0.86 | 2.77 | 3.622 (2) | 174 |
Symmetry code: (i) −x+1, −y+1, −z+1. |
Acknowledgements
The work was supported by the Natural Science Foundation of Zhejiang Province, China (No. M203027).
References
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This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
Hydrazone and its derivatives have shown the potential application in the biological field (Okabe et al., 1993; Hu et al., 2001). As part of the ongoing investigation on anti-cancer compounds, the title compound has recently been prepared in our laboratory and its crystal structure is presented here.
The molecular structure of the title compound is shown in Fig. 1. The asymmetric unit contains two independent molecules. In each, the pyrazine ring and dithiocarbazate moiety are approximately co-planer, r.m.s. deviation being 0.0304 and 0.0418 Å, respectively. The mean plane is oriented with respect to the benzene ring at 49.22 (4)° in one molecule while at 69.76 (7)° in the other. The N3—C5 bond length of 1.284 (3) Å and the N7—C19 bond length of 1.282 (3) Å indicate the typical C═N double bonds. The pyrazine ring and dithiocarbazate moieties are located on the opposite positions of the C═N bonds, showing the E-configuration, which agrees with those found in related compounds (Shan et al., 2006; Shan et al., 2008a,b).
In the crystal the two independent molecules are linked to each other via intermolecular N—H···S hydrogen bonding to form the centro-symmetric supramolecular dimer (Table 1).