Piperidine-1-carboximidamide.

In the title compound, C(6)H(13)N(3), the C=N and C-N bond lengths in the CN(3) unit are 1.3090 (17), and 1.3640 (17) (C-NH(2)) and 1.3773 (16) Å, indicating double- and single-bond character, respectively. The N-C-N angles are 116.82 (12), 119.08 (11) and 124.09 (11)°, showing a deviation of the CN(3) plane from an ideal trigonal-planar geometry. The piperidine ring is in a chair conformation. In the crystal, mol-ecules are linked by N-H⋯N hydrogen bonds, forming a two-dimensional network along the ac plane.

Related literature

For the crystal structure of 4-morpholine­carboxamidine, see: Tiritiris (2012 ▶). For the crystal structure of bis­(piperidin-1-yl)methanone, see: Betz et al. (2011 ▶).

Experimental

Crystal data

C6H13N3

M = 127.19

Monoclinic,

a = 12.2193 (9) Å

b = 5.5784 (5) Å

c = 10.4885 (7) Å

β = 91.887 (4)°

V = 714.55 (10) Å3

Z = 4

Cu Kα radiation

μ = 0.60 mm−1

T = 100 K

0.45 × 0.26 × 0.06 mm

Data collection

Bruker Kappa APEXII DUO diffractometer

Absorption correction: multi-scan (Blessing, 1995 ▶) T min = 0.830, T max = 0.965

4190 measured reflections

1413 independent reflections

1116 reflections with I > 2σ(I)

R int = 0.049

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.112

S = 1.03

1413 reflections

94 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.19 e Å−3

Δρmin = −0.21 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg & Putz, 2005 ▶); software used to prepare material for publication: SHELXL97.

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812044467/go2073sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812044467/go2073Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812044467/go2073Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C6H13N3	F(000) = 280
Mr = 127.19	Dx = 1.182 Mg m−3
Monoclinic, P21/c	Melting point: 409 K
Hall symbol: -P 2ybc	Cu Kα radiation, λ = 1.54178 Å
a = 12.2193 (9) Å	Cell parameters from 4190 reflections
b = 5.5784 (5) Å	θ = 3.6–73.5°
c = 10.4885 (7) Å	µ = 0.60 mm−1
β = 91.887 (4)°	T = 100 K
V = 714.55 (10) Å3	Plate, colorless
Z = 4	0.45 × 0.26 × 0.06 mm

Bruker Kappa APEXII DUO diffractometer	1413 independent reflections
Radiation source: sealed tube	1116 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.049
φ scans, and ω scans	θmax = 73.5°, θmin = 3.6°
Absorption correction: multi-scan (Blessing, 1995)	h = −15→15
Tmin = 0.830, Tmax = 0.965	k = −6→6
4190 measured reflections	l = −12→12

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)] = 0.045	Hydrogen site location: difference Fourier map
wR(F2) = 0.112	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.0625P)2] where P = (Fo2 + 2Fc2)/3
1413 reflections	(Δ/σ)max < 0.001
94 parameters	Δρmax = 0.19 e Å−3
0 restraints	Δρmin = −0.21 e Å−3

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
C1	0.38570 (11)	0.2272 (2)	0.20721 (12)	0.0194 (3)
N1	0.41982 (10)	0.26476 (18)	0.32513 (11)	0.0229 (3)
H11	0.4665 (14)	0.393 (3)	0.3256 (16)	0.031 (4)*
N2	0.40843 (11)	0.37432 (19)	0.10763 (12)	0.0248 (3)
H21	0.4040 (14)	0.315 (3)	0.0240 (18)	0.037 (4)*
H22	0.4598 (14)	0.497 (3)	0.1251 (15)	0.035 (4)*
N3	0.32466 (10)	0.02529 (17)	0.17918 (10)	0.0225 (3)
C2	0.25890 (12)	−0.0007 (2)	0.06138 (13)	0.0270 (4)
H2A	0.2591	−0.1706	0.0341	0.032*
H2B	0.2915	0.0964	−0.0067	0.032*
C3	0.14128 (12)	0.0807 (2)	0.08029 (14)	0.0279 (4)
H3A	0.1403	0.2540	0.1006	0.034*
H3B	0.0972	0.0553	0.0005	0.034*
C4	0.09150 (13)	−0.0602 (2)	0.18847 (14)	0.0275 (3)
H4A	0.0179	0.0040	0.2054	0.033*
H4B	0.0833	−0.2304	0.1631	0.033*
C5	0.16364 (12)	−0.0434 (2)	0.30906 (14)	0.0273 (4)
H5A	0.1341	−0.1493	0.3754	0.033*
H5B	0.1629	0.1231	0.3416	0.033*
C6	0.28172 (12)	−0.1171 (2)	0.28289 (13)	0.0246 (3)
H6A	0.3282	−0.0937	0.3610	0.030*
H6B	0.2837	−0.2892	0.2600	0.030*

	U11	U22	U33	U12	U13	U23
C1	0.0203 (7)	0.0167 (6)	0.0211 (7)	0.0021 (4)	0.0004 (5)	−0.0011 (4)
N1	0.0271 (7)	0.0187 (5)	0.0228 (6)	−0.0023 (4)	−0.0013 (5)	−0.0015 (4)
N2	0.0335 (7)	0.0211 (5)	0.0196 (6)	−0.0053 (5)	−0.0011 (5)	−0.0009 (4)
N3	0.0256 (7)	0.0203 (5)	0.0214 (6)	−0.0032 (4)	−0.0036 (5)	0.0001 (4)
C2	0.0329 (9)	0.0261 (6)	0.0218 (7)	−0.0065 (5)	−0.0021 (6)	−0.0037 (5)
C3	0.0309 (9)	0.0274 (6)	0.0249 (8)	−0.0016 (6)	−0.0091 (6)	0.0017 (5)
C4	0.0261 (8)	0.0268 (7)	0.0295 (8)	0.0009 (5)	−0.0013 (6)	−0.0002 (5)
C5	0.0313 (9)	0.0251 (6)	0.0254 (8)	−0.0022 (5)	0.0012 (6)	0.0016 (5)
C6	0.0292 (8)	0.0197 (6)	0.0247 (7)	−0.0019 (5)	−0.0040 (6)	0.0048 (5)

C1—N1	1.3090 (17)	C3—C4	1.5235 (19)
C1—N2	1.3640 (17)	C3—H3A	0.9900
C1—N3	1.3773 (16)	C3—H3B	0.9900
N1—H11	0.913 (17)	C4—C5	1.521 (2)
N2—H21	0.937 (18)	C4—H4A	0.9900
N2—H22	0.943 (17)	C4—H4B	0.9900
N3—C6	1.4585 (17)	C5—C6	1.534 (2)
N3—C2	1.4587 (17)	C5—H5A	0.9900
C2—C3	1.526 (2)	C5—H5B	0.9900
C2—H2A	0.9900	C6—H6A	0.9900
C2—H2B	0.9900	C6—H6B	0.9900
N1—C1—N2	124.09 (11)	C2—C3—H3B	109.6
N1—C1—N3	119.08 (11)	H3A—C3—H3B	108.2
N2—C1—N3	116.82 (12)	C5—C4—C3	110.67 (12)
C1—N1—H11	108.1 (11)	C5—C4—H4A	109.5
C1—N2—H21	119.8 (10)	C3—C4—H4A	109.5
C1—N2—H22	116.1 (10)	C5—C4—H4B	109.5
H21—N2—H22	117.2 (14)	C3—C4—H4B	109.5
C1—N3—C6	119.46 (11)	H4A—C4—H4B	108.1
C1—N3—C2	122.78 (10)	C4—C5—C6	110.95 (12)
C6—N3—C2	112.09 (10)	C4—C5—H5A	109.4
N3—C2—C3	110.80 (11)	C6—C5—H5A	109.4
N3—C2—H2A	109.5	C4—C5—H5B	109.4
C3—C2—H2A	109.5	C6—C5—H5B	109.4
N3—C2—H2B	109.5	H5A—C5—H5B	108.0
C3—C2—H2B	109.5	N3—C6—C5	110.55 (11)
H2A—C2—H2B	108.1	N3—C6—H6A	109.5
C4—C3—C2	110.12 (11)	C5—C6—H6A	109.5
C4—C3—H3A	109.6	N3—C6—H6B	109.5
C2—C3—H3A	109.6	C5—C6—H6B	109.5
C4—C3—H3B	109.6	H6A—C6—H6B	108.1
N1—C1—N3—C6	11.63 (18)	N3—C2—C3—C4	−56.89 (14)
N2—C1—N3—C6	−169.57 (11)	C2—C3—C4—C5	53.91 (15)
N1—C1—N3—C2	162.94 (12)	C3—C4—C5—C6	−53.30 (14)
N2—C1—N3—C2	−18.25 (18)	C1—N3—C6—C5	95.35 (14)
C1—N3—C2—C3	−93.09 (14)	C2—N3—C6—C5	−58.83 (14)
C6—N3—C2—C3	60.10 (13)	C4—C5—C6—N3	55.17 (13)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H21···N1i	0.94 (2)	2.15 (2)	3.071 (1)	168 (1)
N2—H22···N1ii	0.94 (2)	2.15 (2)	3.090 (1)	177 (1)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H21⋯N1i	0.94 (2)	2.15 (2)	3.071 (1)	168 (1)
N2—H22⋯N1ii	0.94 (2)	2.15 (2)	3.090 (1)	177 (1)

Symmetry codes: (i) ; (ii) .