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The mol­ecules of the title compound, C15H20N6S, are linked into centrosymmetric dimers by N—H...N intermolecular hydrogen bonds, forming a monoclinic crystal structure.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802009170/cv6115sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536802009170/cv6115Isup2.hkl
Contains datablock I

CCDC reference: 189412

Key indicators

  • Single-crystal X-ray study
  • T = 291 K
  • Mean [sigma](C-C) = 0.006 Å
  • R factor = 0.047
  • wR factor = 0.090
  • Data-to-parameter ratio = 13.4

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


Yellow Alert Alert Level C:
PLAT_420 Alert C D-H Without Acceptor N(6) - H(6B) ?
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
1 Alert Level C = Please check

Computing details top

Data collection: XSCANS (Siemens, 1994); cell refinement: XSCANS; data reduction: XSCANS; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 1999) and Visualizer Program (Cambridge Crystallographic Data Centre, 2002); software used to prepare material for publication: SHELXL97 and PLATON.

2-{[1-(2-Aminophenyl)ethylidene]hydrazino}-5-piperidyl-1,3,4-thiadiazole top
Crystal data top
C15H20N6SF(000) = 672
Mr = 316.43Dx = 1.333 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 11.291 (1) ÅCell parameters from 37 reflections
b = 13.644 (2) Åθ = 4.7–9.4°
c = 11.384 (2) ŵ = 0.21 mm1
β = 115.94 (1)°T = 291 K
V = 1577.1 (4) Å3Prism, dark red
Z = 40.40 × 0.12 × 0.12 mm
Data collection top
Siemens P4/PC
diffractometer
Rint = 0.044
Radiation source: fine-focus sealed tubeθmax = 25.0°, θmin = 2.0°
Graphite monochromatorh = 013
ω scansk = 016
2925 measured reflectionsl = 1312
2777 independent reflections3 standard reflections every 97 reflections
1302 reflections with I > 2σ(I) intensity decay: <2%
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)] = 0.047Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.090H atoms treated by a mixture of independent and constrained refinement
S = 0.88 w = 1/[σ2(Fo2) + (0.0186P)2]
where P = (Fo2 + 2Fc2)/3
2777 reflections(Δ/σ)max = 0.012
208 parametersΔρmax = 0.16 e Å3
0 restraintsΔρmin = 0.19 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
S10.22469 (10)0.14577 (7)0.39303 (11)0.0678 (3)
N10.1993 (3)0.06257 (19)0.3559 (3)0.0605 (8)
N20.1134 (3)0.0259 (2)0.4026 (4)0.0714 (10)
H2A0.056 (4)0.055 (3)0.405 (4)0.086*
N30.0722 (3)0.11234 (19)0.5016 (3)0.0711 (10)
N40.1013 (3)0.2124 (2)0.5202 (3)0.0724 (9)
N50.2122 (3)0.3343 (2)0.4646 (3)0.0822 (11)
N60.4410 (4)0.0571 (3)0.3625 (4)0.0917 (13)
H6A0.374 (4)0.022 (3)0.374 (4)0.110*
H6B0.514 (4)0.034 (3)0.375 (4)0.110*
C10.2867 (3)0.1935 (2)0.2790 (3)0.0532 (9)
C20.4049 (3)0.1476 (3)0.3015 (3)0.0597 (9)
C30.4934 (4)0.1938 (3)0.2638 (4)0.0712 (11)
H30.57340.16380.28190.085*
C40.4646 (4)0.2825 (3)0.2009 (4)0.0747 (12)
H40.52510.31230.17720.090*
C50.3471 (4)0.3270 (3)0.1730 (4)0.0764 (12)
H50.32580.38630.12820.092*
C60.2598 (4)0.2826 (2)0.2125 (3)0.0665 (11)
H60.18010.31350.19370.080*
C70.1899 (3)0.1539 (2)0.3232 (3)0.0562 (9)
C80.1281 (3)0.0693 (2)0.4373 (4)0.0578 (10)
C90.1774 (4)0.2402 (2)0.4687 (4)0.0634 (11)
C100.3186 (4)0.3580 (3)0.4292 (4)0.0950 (15)
H10A0.31740.31190.36390.114*
H10B0.40250.35140.50560.114*
C110.3058 (4)0.4578 (3)0.3778 (4)0.0913 (14)
H11A0.23190.46020.29190.110*
H11B0.38470.47420.36810.110*
C120.2857 (4)0.5331 (3)0.4638 (4)0.0916 (14)
H12B0.36460.53770.54580.110*
H12A0.27020.59670.42150.110*
C130.1706 (4)0.5061 (3)0.4901 (5)0.0901 (14)
H13A0.16380.55260.55140.108*
H13B0.09020.51010.40950.108*
C140.1840 (4)0.4058 (3)0.5445 (4)0.0910 (15)
H14A0.25450.40490.63250.109*
H14B0.10300.38760.54900.109*
C150.0905 (4)0.2196 (3)0.3351 (4)0.0795 (12)
H15A0.09870.28420.30620.095*
H15B0.00370.19480.28200.095*
H15C0.10500.22210.42460.095*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0840 (7)0.0547 (5)0.0984 (7)0.0063 (6)0.0712 (6)0.0021 (6)
N10.071 (2)0.0586 (18)0.073 (2)0.0077 (15)0.0517 (19)0.0016 (15)
N20.086 (3)0.0543 (19)0.113 (3)0.0018 (17)0.080 (2)0.0040 (19)
N30.089 (2)0.0532 (17)0.105 (3)0.0013 (16)0.073 (2)0.0050 (16)
N40.094 (2)0.0579 (18)0.105 (3)0.0004 (17)0.080 (2)0.0018 (18)
N50.111 (3)0.0509 (18)0.136 (3)0.0027 (18)0.101 (3)0.0052 (19)
N60.081 (3)0.076 (2)0.146 (4)0.015 (2)0.076 (3)0.031 (2)
C10.056 (2)0.059 (2)0.057 (2)0.0011 (17)0.036 (2)0.0012 (18)
C20.062 (2)0.061 (2)0.068 (2)0.006 (2)0.039 (2)0.002 (2)
C30.073 (3)0.073 (3)0.093 (3)0.007 (2)0.060 (3)0.009 (2)
C40.089 (3)0.071 (3)0.092 (3)0.015 (2)0.066 (3)0.001 (2)
C50.096 (3)0.070 (3)0.084 (3)0.005 (2)0.058 (3)0.013 (2)
C60.077 (3)0.065 (2)0.076 (3)0.005 (2)0.051 (3)0.008 (2)
C70.066 (2)0.056 (2)0.060 (2)0.0023 (19)0.040 (2)0.0003 (18)
C80.064 (2)0.052 (2)0.075 (3)0.0067 (18)0.047 (2)0.0043 (19)
C90.076 (3)0.055 (2)0.085 (3)0.0055 (19)0.059 (3)0.000 (2)
C100.126 (4)0.065 (2)0.156 (4)0.002 (3)0.119 (4)0.008 (3)
C110.116 (4)0.076 (3)0.119 (4)0.010 (3)0.086 (3)0.002 (3)
C120.122 (4)0.062 (2)0.121 (4)0.006 (3)0.080 (3)0.001 (2)
C130.111 (4)0.065 (2)0.127 (4)0.002 (2)0.083 (3)0.013 (2)
C140.135 (4)0.061 (2)0.130 (4)0.004 (2)0.106 (4)0.014 (2)
C150.078 (3)0.079 (3)0.110 (3)0.013 (2)0.067 (3)0.028 (2)
Geometric parameters (Å, º) top
S1—C81.736 (3)C4—H40.9300
S1—C91.757 (3)C5—C61.389 (4)
N1—C71.292 (4)C5—H50.9300
N1—N21.387 (3)C6—H60.9300
N2—C81.347 (4)C7—C151.487 (4)
N2—H2A0.76 (3)C10—C111.465 (5)
N3—C81.297 (4)C10—H10A0.9700
N3—N41.398 (4)C10—H10B0.9700
N4—C91.292 (4)C11—C121.502 (5)
N5—C91.350 (4)C11—H11A0.9700
N5—C141.460 (4)C11—H11B0.9700
N5—C101.460 (4)C12—C131.503 (5)
N6—C21.388 (5)C12—H12B0.9700
N6—H6A0.95 (4)C12—H12A0.9700
N6—H6B0.84 (4)C13—C141.482 (5)
C1—C61.393 (4)C13—H13A0.9700
C1—C21.393 (4)C13—H13B0.9700
C1—C71.490 (4)C14—H14A0.9700
C2—C31.397 (4)C14—H14B0.9700
C3—C41.371 (5)C15—H15A0.9600
C3—H30.9300C15—H15B0.9600
C4—C51.363 (5)C15—H15C0.9600
C8—S1—C986.22 (15)N4—C9—S1114.4 (3)
C7—N1—N2118.4 (3)N5—C9—S1121.7 (2)
C8—N2—N1116.3 (3)N5—C10—C11111.5 (3)
C8—N2—H2A119 (3)N5—C10—H10A109.3
N1—N2—H2A125 (3)C11—C10—H10A109.3
C8—N3—N4112.8 (3)N5—C10—H10B109.3
C9—N4—N3112.1 (3)C11—C10—H10B109.3
C9—N5—C14117.9 (3)H10A—C10—H10B108.0
C9—N5—C10120.4 (3)C10—C11—C12113.1 (3)
C14—N5—C10117.0 (3)C10—C11—H11A109.0
C2—N6—H6A116 (2)C12—C11—H11A109.0
C2—N6—H6B119 (3)C10—C11—H11B109.0
H6A—N6—H6B124 (4)C12—C11—H11B109.0
C6—C1—C2117.1 (3)H11A—C11—H11B107.8
C6—C1—C7118.8 (3)C13—C12—C11110.7 (3)
C2—C1—C7124.1 (3)C13—C12—H12B109.5
N6—C2—C1122.6 (3)C11—C12—H12B109.5
N6—C2—C3117.5 (3)C13—C12—H12A109.5
C1—C2—C3119.8 (3)C11—C12—H12A109.5
C4—C3—C2121.4 (3)H12B—C12—H12A108.1
C4—C3—H3119.3C14—C13—C12111.7 (3)
C2—C3—H3119.3C14—C13—H13A109.3
C5—C4—C3119.9 (3)C12—C13—H13A109.3
C5—C4—H4120.1C14—C13—H13B109.3
C3—C4—H4120.1C12—C13—H13B109.3
C4—C5—C6119.1 (3)H13A—C13—H13B107.9
C4—C5—H5120.4N5—C14—C13111.5 (3)
C6—C5—H5120.4N5—C14—H14A109.3
C5—C6—C1122.7 (3)C13—C14—H14A109.3
C5—C6—H6118.7N5—C14—H14B109.3
C1—C6—H6118.7C13—C14—H14B109.3
N1—C7—C15121.7 (3)H14A—C14—H14B108.0
N1—C7—C1117.9 (3)C7—C15—H15A109.5
C15—C7—C1120.4 (3)C7—C15—H15B109.5
N3—C8—N2125.1 (3)H15A—C15—H15B109.5
N3—C8—S1114.5 (2)C7—C15—H15C109.5
N2—C8—S1120.5 (2)H15A—C15—H15C109.5
N4—C9—N5123.8 (3)H15B—C15—H15C109.5
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2A···N3i0.76 (3)2.28 (3)2.995 (3)156 (4)
N6—H6A···N10.95 (4)1.98 (4)2.698 (4)131 (3)
N6—H6A···S10.95 (4)2.91 (4)3.806 (3)159 (3)
Symmetry code: (i) x, y, z+1.
 

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