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The title compound, C6H8N4S, crystallizes as the thione tautomer, with intra­molecular N...H—N and S...H—N hydrogen bonds, and π–π stacking along the b axis. Inter­molecular N...H—N hydrogen bonds link the mol­ecules into one-dimensional sheets stacked along the c axis.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805019057/jh6009sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805019057/jh6009Isup2.hkl
Contains datablock I

CCDC reference: 277708

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.035
  • wR factor = 0.107
  • Data-to-parameter ratio = 15.6

checkCIF/PLATON results

No syntax errors found



Alert level A PLAT707_ALERT_1_A D...A Calc 19.064(3), Rep 3.058(2), Dev.. 5335.33 Sigma N2 -N4 1.555 4.565 PLAT726_ALERT_1_A H...A Calc 18.83000, Rep 2.21000 Dev... 16.62 Ang. H5 -N4 1.555 4.565 PLAT728_ALERT_1_A D-H..A Calc 105.00, Rep 169.00 Dev... 64.00 Deg. N2 -H5 -N4 1.555 1.555 4.565
Alert level C PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature . 293 K PLAT230_ALERT_2_C Hirshfeld Test Diff for S1 - C6 .. 5.63 su PLAT352_ALERT_3_C Short N-H Bond (0.87A) N4 - H7 ... 0.75 Ang. PLAT420_ALERT_2_C D-H Without Acceptor N4 - H8 ... ?
3 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 5 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 5 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 1 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 and PLATON; software used to prepare material for publication: Please provide missing details.

N-(Pyridin-2-yl)hydrazinecarbothioamide top
Crystal data top
C6H8N4SF(000) = 704
Mr = 168.22Dx = 1.477 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 4378 reflections
a = 15.5846 (17) Åθ = 2.7–28.2°
b = 10.1592 (11) ŵ = 0.36 mm1
c = 11.1622 (12) ÅT = 293 K
β = 121.118 (2)°Blocks, light yellow
V = 1513.0 (3) Å30.32 × 0.28 × 0.22 mm
Z = 8
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
1604 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.015
Graphite monochromatorθmax = 28.2°, θmin = 2.7°
ω scansh = 2016
4378 measured reflectionsk = 1312
1748 independent reflectionsl = 1114
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.035Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.107H atoms treated by a mixture of independent and constrained refinement
S = 1.12 w = 1/[σ2(Fo2) + (0.0614P)2 + 0.5476P]
where P = (Fo2 + 2Fc2)/3
1748 reflections(Δ/σ)max < 0.001
112 parametersΔρmax = 0.24 e Å3
0 restraintsΔρmin = 0.22 e Å3
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S10.35725 (3)0.63917 (4)0.22149 (4)0.04559 (17)
N40.38305 (14)0.63960 (13)0.02915 (16)0.0474 (3)
N10.39857 (9)0.25571 (11)0.03824 (12)0.0383 (3)
C20.38651 (13)0.02148 (15)0.04013 (18)0.0500 (4)
H20.39160.05960.00560.060*
N20.37094 (9)0.38463 (11)0.18943 (12)0.0381 (3)
H50.36600.38250.26270.046*
C60.37261 (10)0.50765 (13)0.14174 (13)0.0347 (3)
C10.40289 (13)0.13602 (14)0.00925 (17)0.0464 (4)
H10.41790.13070.07970.056*
N30.38371 (10)0.51774 (11)0.03185 (13)0.0397 (3)
C50.37598 (9)0.26172 (13)0.13774 (13)0.0336 (3)
C30.36214 (12)0.02914 (15)0.14268 (17)0.0504 (4)
H30.35000.04710.17770.061*
C40.35599 (11)0.15032 (15)0.19251 (16)0.0436 (3)
H40.33900.15790.26080.052*
H80.4457 (18)0.672 (2)0.032 (3)0.079 (7)*
H70.343 (2)0.680 (3)0.029 (3)0.083 (8)*
H60.3886 (13)0.454 (2)0.005 (2)0.051 (5)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0657 (3)0.0377 (2)0.0445 (3)0.00352 (14)0.0364 (2)0.00588 (13)
N40.0754 (10)0.0318 (6)0.0496 (8)0.0037 (6)0.0426 (8)0.0021 (5)
N10.0512 (7)0.0328 (6)0.0366 (6)0.0007 (5)0.0269 (5)0.0015 (5)
C20.0604 (9)0.0331 (7)0.0477 (8)0.0007 (6)0.0218 (7)0.0063 (6)
N20.0552 (7)0.0349 (6)0.0357 (6)0.0013 (5)0.0316 (5)0.0008 (4)
C60.0410 (6)0.0349 (7)0.0323 (6)0.0004 (5)0.0219 (5)0.0017 (5)
C10.0603 (9)0.0393 (8)0.0419 (8)0.0016 (6)0.0280 (7)0.0062 (6)
N30.0630 (7)0.0292 (6)0.0397 (6)0.0037 (5)0.0357 (6)0.0032 (5)
C50.0357 (6)0.0342 (7)0.0295 (6)0.0003 (5)0.0157 (5)0.0007 (5)
C30.0588 (9)0.0347 (7)0.0490 (8)0.0050 (6)0.0217 (7)0.0055 (6)
C40.0527 (8)0.0415 (8)0.0393 (7)0.0032 (6)0.0256 (6)0.0053 (6)
Geometric parameters (Å, º) top
S1—C61.6897 (13)N2—C51.3947 (16)
N4—N31.4104 (16)N2—H50.8600
N4—H80.92 (2)C6—N31.3283 (17)
N4—H70.74 (3)C1—H10.9300
N1—C51.3286 (17)N3—H60.79 (2)
N1—C11.3420 (17)C5—C41.3960 (19)
C2—C11.367 (2)C3—C41.374 (2)
C2—C31.382 (3)C3—H30.9300
C2—H20.9300C4—H40.9300
N2—C61.3639 (16)
N3—N4—H8102.7 (15)N1—C1—H1118.2
N3—N4—H7106 (2)C2—C1—H1118.2
H8—N4—H7112 (3)C6—N3—N4122.79 (12)
C5—N1—C1117.44 (12)C6—N3—H6120.7 (14)
C1—C2—C3118.33 (14)N4—N3—H6116.4 (14)
C1—C2—H2120.8N1—C5—N2118.87 (11)
C3—C2—H2120.8N1—C5—C4122.98 (12)
C6—N2—C5129.97 (11)N2—C5—C4118.14 (12)
C6—N2—H5115.0C4—C3—C2119.48 (14)
C5—N2—H5115.0C4—C3—H3120.3
N3—C6—N2117.96 (11)C2—C3—H3120.3
N3—C6—S1123.16 (10)C3—C4—C5118.09 (15)
N2—C6—S1118.85 (10)C3—C4—H4121.0
N1—C1—C2123.65 (15)C5—C4—H4121.0
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H5···N4i0.862.213.058 (2)169
N4—H7···S10.75 (3)2.72 (3)3.025 (2)107 (2)
N3—H6···N10.79 (2)2.06 (2)2.6698 (16)134.0 (19)
Symmetry code: (i) x+1/2, y+3/2, z+1/2.
 

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