2-{[1-(2-Amino­phenyl)­ethyl­idene]­hydrazino}-5-piperidyl-1,3,4-thia­diazo­le

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

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


 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

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Computing details

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

Crystal data

C15H20N6S	F(000) = 672
Mr = 316.43	Dx = 1.333 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 11.291 (1) Å	Cell parameters from 37 reflections
b = 13.644 (2) Å	θ = 4.7–9.4°
c = 11.384 (2) Å	µ = 0.21 mm^−1
β = 115.94 (1)°	T = 291 K
V = 1577.1 (4) Å^3	Prism, dark red
Z = 4	0.40 × 0.12 × 0.12 mm

Data collection

Siemens P4/PC diffractometer	Rint = 0.044
Radiation source: fine-focus sealed tube	θmax = 25.0°, θmin = 2.0°
Graphite monochromator	h = 0→13
ω scans	k = 0→16
2925 measured reflections	l = −13→12
2777 independent reflections	3 standard reflections every 97 reflections
1302 reflections with I > 2σ(I)	intensity decay: <2%

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.090	H atoms treated by a mixture of independent and constrained refinement
S = 0.88	w = 1/[σ^2(Fo^2) + (0.0186P)^2] where P = (Fo^2 + 2Fc^2)/3
2777 reflections	(Δ/σ)max = 0.012
208 parameters	Δρmax = 0.16 e Å^−3
0 restraints	Δρmin = −0.19 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
S1	0.22469 (10)	0.14577 (7)	0.39303 (11)	0.0678 (3)
N1	0.1993 (3)	−0.06257 (19)	0.3559 (3)	0.0605 (8)
N2	0.1134 (3)	−0.0259 (2)	0.4026 (4)	0.0714 (10)
H2A	0.056 (4)	−0.055 (3)	0.405 (4)	0.086*
N3	0.0722 (3)	0.11234 (19)	0.5016 (3)	0.0711 (10)
N4	0.1013 (3)	0.2124 (2)	0.5202 (3)	0.0724 (9)
N5	0.2122 (3)	0.3343 (2)	0.4646 (3)	0.0822 (11)
N6	0.4410 (4)	−0.0571 (3)	0.3625 (4)	0.0917 (13)
H6A	0.374 (4)	−0.022 (3)	0.374 (4)	0.110*
H6B	0.514 (4)	−0.034 (3)	0.375 (4)	0.110*
C1	0.2867 (3)	−0.1935 (2)	0.2790 (3)	0.0532 (9)
C2	0.4049 (3)	−0.1476 (3)	0.3015 (3)	0.0597 (9)
C3	0.4934 (4)	−0.1938 (3)	0.2638 (4)	0.0712 (11)
H3	0.5734	−0.1638	0.2819	0.085*
C4	0.4646 (4)	−0.2825 (3)	0.2009 (4)	0.0747 (12)
H4	0.5251	−0.3123	0.1772	0.090*
C5	0.3471 (4)	−0.3270 (3)	0.1730 (4)	0.0764 (12)
H5	0.3258	−0.3863	0.1282	0.092*
C6	0.2598 (4)	−0.2826 (2)	0.2125 (3)	0.0665 (11)
H6	0.1801	−0.3135	0.1937	0.080*
C7	0.1899 (3)	−0.1539 (2)	0.3232 (3)	0.0562 (9)
C8	0.1281 (3)	0.0693 (2)	0.4373 (4)	0.0578 (10)
C9	0.1774 (4)	0.2402 (2)	0.4687 (4)	0.0634 (11)
C10	0.3186 (4)	0.3580 (3)	0.4292 (4)	0.0950 (15)
H10A	0.3174	0.3119	0.3639	0.114*
H10B	0.4025	0.3514	0.5056	0.114*
C11	0.3058 (4)	0.4578 (3)	0.3778 (4)	0.0913 (14)
H11A	0.2319	0.4602	0.2919	0.110*
H11B	0.3847	0.4742	0.3681	0.110*
C12	0.2857 (4)	0.5331 (3)	0.4638 (4)	0.0916 (14)
H12B	0.3646	0.5377	0.5458	0.110*
H12A	0.2702	0.5967	0.4215	0.110*
C13	0.1706 (4)	0.5061 (3)	0.4901 (5)	0.0901 (14)
H13A	0.1638	0.5526	0.5514	0.108*
H13B	0.0902	0.5101	0.4095	0.108*
C14	0.1840 (4)	0.4058 (3)	0.5445 (4)	0.0910 (15)
H14A	0.2545	0.4049	0.6325	0.109*
H14B	0.1030	0.3876	0.5490	0.109*
C15	0.0905 (4)	−0.2196 (3)	0.3351 (4)	0.0795 (12)
H15A	0.0987	−0.2842	0.3062	0.095*
H15B	0.0037	−0.1948	0.2820	0.095*
H15C	0.1050	−0.2221	0.4246	0.095*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0840 (7)	0.0547 (5)	0.0984 (7)	0.0063 (6)	0.0712 (6)	0.0021 (6)
N1	0.071 (2)	0.0586 (18)	0.073 (2)	0.0077 (15)	0.0517 (19)	0.0016 (15)
N2	0.086 (3)	0.0543 (19)	0.113 (3)	0.0018 (17)	0.080 (2)	−0.0040 (19)
N3	0.089 (2)	0.0532 (17)	0.105 (3)	−0.0013 (16)	0.073 (2)	−0.0050 (16)
N4	0.094 (2)	0.0579 (18)	0.105 (3)	−0.0004 (17)	0.080 (2)	−0.0018 (18)
N5	0.111 (3)	0.0509 (18)	0.136 (3)	−0.0027 (18)	0.101 (3)	−0.0052 (19)
N6	0.081 (3)	0.076 (2)	0.146 (4)	−0.015 (2)	0.076 (3)	−0.031 (2)
C1	0.056 (2)	0.059 (2)	0.057 (2)	0.0011 (17)	0.036 (2)	0.0012 (18)
C2	0.062 (2)	0.061 (2)	0.068 (2)	0.006 (2)	0.039 (2)	0.002 (2)
C3	0.073 (3)	0.073 (3)	0.093 (3)	0.007 (2)	0.060 (3)	0.009 (2)
C4	0.089 (3)	0.071 (3)	0.092 (3)	0.015 (2)	0.066 (3)	0.001 (2)
C5	0.096 (3)	0.070 (3)	0.084 (3)	0.005 (2)	0.058 (3)	−0.013 (2)
C6	0.077 (3)	0.065 (2)	0.076 (3)	−0.005 (2)	0.051 (3)	−0.008 (2)
C7	0.066 (2)	0.056 (2)	0.060 (2)	0.0023 (19)	0.040 (2)	0.0003 (18)
C8	0.064 (2)	0.052 (2)	0.075 (3)	0.0067 (18)	0.047 (2)	0.0043 (19)
C9	0.076 (3)	0.055 (2)	0.085 (3)	0.0055 (19)	0.059 (3)	0.000 (2)
C10	0.126 (4)	0.065 (2)	0.156 (4)	0.002 (3)	0.119 (4)	0.008 (3)
C11	0.116 (4)	0.076 (3)	0.119 (4)	−0.010 (3)	0.086 (3)	−0.002 (3)
C12	0.122 (4)	0.062 (2)	0.121 (4)	−0.006 (3)	0.080 (3)	−0.001 (2)
C13	0.111 (4)	0.065 (2)	0.127 (4)	0.002 (2)	0.083 (3)	−0.013 (2)
C14	0.135 (4)	0.061 (2)	0.130 (4)	−0.004 (2)	0.106 (4)	−0.014 (2)
C15	0.078 (3)	0.079 (3)	0.110 (3)	−0.013 (2)	0.067 (3)	−0.028 (2)

Geometric parameters (Å, º)

S1—C8	1.736 (3)	C4—H4	0.9300
S1—C9	1.757 (3)	C5—C6	1.389 (4)
N1—C7	1.292 (4)	C5—H5	0.9300
N1—N2	1.387 (3)	C6—H6	0.9300
N2—C8	1.347 (4)	C7—C15	1.487 (4)
N2—H2A	0.76 (3)	C10—C11	1.465 (5)
N3—C8	1.297 (4)	C10—H10A	0.9700
N3—N4	1.398 (4)	C10—H10B	0.9700
N4—C9	1.292 (4)	C11—C12	1.502 (5)
N5—C9	1.350 (4)	C11—H11A	0.9700
N5—C14	1.460 (4)	C11—H11B	0.9700
N5—C10	1.460 (4)	C12—C13	1.503 (5)
N6—C2	1.388 (5)	C12—H12B	0.9700
N6—H6A	0.95 (4)	C12—H12A	0.9700
N6—H6B	0.84 (4)	C13—C14	1.482 (5)
C1—C6	1.393 (4)	C13—H13A	0.9700
C1—C2	1.393 (4)	C13—H13B	0.9700
C1—C7	1.490 (4)	C14—H14A	0.9700
C2—C3	1.397 (4)	C14—H14B	0.9700
C3—C4	1.371 (5)	C15—H15A	0.9600
C3—H3	0.9300	C15—H15B	0.9600
C4—C5	1.363 (5)	C15—H15C	0.9600
C8—S1—C9	86.22 (15)	N4—C9—S1	114.4 (3)
C7—N1—N2	118.4 (3)	N5—C9—S1	121.7 (2)
C8—N2—N1	116.3 (3)	N5—C10—C11	111.5 (3)
C8—N2—H2A	119 (3)	N5—C10—H10A	109.3
N1—N2—H2A	125 (3)	C11—C10—H10A	109.3
C8—N3—N4	112.8 (3)	N5—C10—H10B	109.3
C9—N4—N3	112.1 (3)	C11—C10—H10B	109.3
C9—N5—C14	117.9 (3)	H10A—C10—H10B	108.0
C9—N5—C10	120.4 (3)	C10—C11—C12	113.1 (3)
C14—N5—C10	117.0 (3)	C10—C11—H11A	109.0
C2—N6—H6A	116 (2)	C12—C11—H11A	109.0
C2—N6—H6B	119 (3)	C10—C11—H11B	109.0
H6A—N6—H6B	124 (4)	C12—C11—H11B	109.0
C6—C1—C2	117.1 (3)	H11A—C11—H11B	107.8
C6—C1—C7	118.8 (3)	C13—C12—C11	110.7 (3)
C2—C1—C7	124.1 (3)	C13—C12—H12B	109.5
N6—C2—C1	122.6 (3)	C11—C12—H12B	109.5
N6—C2—C3	117.5 (3)	C13—C12—H12A	109.5
C1—C2—C3	119.8 (3)	C11—C12—H12A	109.5
C4—C3—C2	121.4 (3)	H12B—C12—H12A	108.1
C4—C3—H3	119.3	C14—C13—C12	111.7 (3)
C2—C3—H3	119.3	C14—C13—H13A	109.3
C5—C4—C3	119.9 (3)	C12—C13—H13A	109.3
C5—C4—H4	120.1	C14—C13—H13B	109.3
C3—C4—H4	120.1	C12—C13—H13B	109.3
C4—C5—C6	119.1 (3)	H13A—C13—H13B	107.9
C4—C5—H5	120.4	N5—C14—C13	111.5 (3)
C6—C5—H5	120.4	N5—C14—H14A	109.3
C5—C6—C1	122.7 (3)	C13—C14—H14A	109.3
C5—C6—H6	118.7	N5—C14—H14B	109.3
C1—C6—H6	118.7	C13—C14—H14B	109.3
N1—C7—C15	121.7 (3)	H14A—C14—H14B	108.0
N1—C7—C1	117.9 (3)	C7—C15—H15A	109.5
C15—C7—C1	120.4 (3)	C7—C15—H15B	109.5
N3—C8—N2	125.1 (3)	H15A—C15—H15B	109.5
N3—C8—S1	114.5 (2)	C7—C15—H15C	109.5
N2—C8—S1	120.5 (2)	H15A—C15—H15C	109.5
N4—C9—N5	123.8 (3)	H15B—C15—H15C	109.5

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···N3^i	0.76 (3)	2.28 (3)	2.995 (3)	156 (4)
N6—H6A···N1	0.95 (4)	1.98 (4)	2.698 (4)	131 (3)
N6—H6A···S1	0.95 (4)	2.91 (4)	3.806 (3)	159 (3)

Symmetry code: (i) −x, −y, −z+1.