4-Morpholine-carboxamidine.

In the crystal structure of the title compound, C(5)H(11)N(3)O, the C=N and C-N bond lengths in the CN(3) unit are 1.2971 (14), 1.3595 (14) (NH(2)) and 1.3902 (13) Å, indicating double- and single-bond character, respectively. The N-C-N angles are 115.49 (9)°, 119.68 (10)° and 124.83 (10)°, showing a deviation of the CN(3) plane from an ideal trigonal-planar geometry. The morpholine ring is in a chair conformation. In the crystal, the mol-ecules are linked by N-H⋯N and N-H⋯O hydrogen bonds, generating a three-dimensional network.

Related literature

For the synthesis of carboxamides by amidination of secondary amines with 4-benzyl-3,5-dimethyl-1H-pyrazole-1-carboxamidine hydro­chloride, see: Dräger et al. (2002 ▶). For the crystal structure of 4,4′-carbonyl-dimorpholine, see: Zhou et al. (2003 ▶).

Experimental

Crystal data

C5H11N3O

M = 129.17

Tetragonal,

a = 16.5910 (6) Å

c = 9.7939 (3) Å

V = 2695.9 (2) Å3

Z = 16

Mo Kα radiation

μ = 0.09 mm−1

T = 100 K

0.17 × 0.15 × 0.13 mm

Data collection

Bruker–Nonius KappaCCD diffractometer

2889 measured reflections

1628 independent reflections

1341 reflections with I > 2σ(I)

R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.091

S = 1.06

1628 reflections

94 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.27 e Å−3

Δρmin = −0.19 e Å−3

Data collection: COLLECT (Hooft, 2004 ▶); cell refinement: SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: SCALEPACK; 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/S1600536812042201/zl2510sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812042201/zl2510Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812042201/zl2510Isup3.cml

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

C5H11N3O	Dx = 1.273 Mg m−3
Mr = 129.17	Melting point: 433 K
Tetragonal, I41/a	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -I 4ad	Cell parameters from 5017 reflections
a = 16.5910 (6) Å	θ = 0.4–28.3°
c = 9.7939 (3) Å	µ = 0.09 mm−1
V = 2695.9 (2) Å3	T = 100 K
Z = 16	Polyhedral, colorless
F(000) = 1120	0.17 × 0.15 × 0.13 mm

Bruker–Nonius KappaCCD diffractometer	1341 reflections with I > 2σ(I)
Radiation source: sealed tube	Rint = 0.022
Graphite monochromator	θmax = 28.1°, θmin = 2.5°
φ scans, and ω scans	h = −21→21
2889 measured reflections	k = −21→21
1628 independent 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)] = 0.037	Hydrogen site location: difference Fourier map
wR(F2) = 0.091	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ2(Fo2) + (0.0306P)2 + 2.2674P] where P = (Fo2 + 2Fc2)/3
1628 reflections	(Δ/σ)max < 0.001
94 parameters	Δρmax = 0.27 e Å−3
0 restraints	Δρmin = −0.19 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
N1	−0.14446 (6)	0.03950 (6)	0.30140 (11)	0.0159 (2)
H11	−0.1813 (9)	0.0047 (9)	0.2645 (15)	0.019 (4)*
N2	−0.06037 (6)	−0.03560 (6)	0.15536 (11)	0.0157 (2)
H21	−0.1050 (9)	−0.0608 (9)	0.1248 (16)	0.022 (4)*
H22	−0.0127 (10)	−0.0587 (9)	0.1491 (16)	0.025 (4)*
N3	−0.00555 (5)	0.05719 (5)	0.30717 (10)	0.0125 (2)
C1	−0.07396 (6)	0.02009 (6)	0.25455 (11)	0.0114 (2)
C2	0.06247 (7)	0.07582 (7)	0.21681 (12)	0.0158 (3)
H2A	0.0507	0.1252	0.1636	0.019*
H2B	0.0711	0.0309	0.1519	0.019*
C3	0.13724 (7)	0.08832 (7)	0.30179 (13)	0.0190 (3)
H3A	0.1502	0.0379	0.3513	0.023*
H3B	0.1832	0.1013	0.2413	0.023*
O1	0.12587 (5)	0.15229 (5)	0.39777 (9)	0.0192 (2)
C4	0.06078 (7)	0.13290 (8)	0.48713 (12)	0.0199 (3)
H4A	0.0535	0.1772	0.5537	0.024*
H4B	0.0742	0.0834	0.5387	0.024*
C5	−0.01736 (7)	0.11994 (7)	0.40977 (12)	0.0170 (3)
H5A	−0.0605	0.1036	0.4740	0.020*
H5B	−0.0340	0.1708	0.3649	0.020*

	U11	U22	U33	U12	U13	U23
N1	0.0111 (4)	0.0149 (5)	0.0217 (5)	−0.0013 (4)	0.0005 (4)	−0.0051 (4)
N2	0.0106 (5)	0.0143 (5)	0.0222 (5)	0.0007 (4)	−0.0018 (4)	−0.0082 (4)
N3	0.0106 (4)	0.0134 (4)	0.0137 (5)	−0.0020 (3)	0.0023 (4)	−0.0056 (4)
C1	0.0129 (5)	0.0088 (5)	0.0126 (5)	−0.0004 (4)	−0.0008 (4)	−0.0002 (4)
C2	0.0142 (5)	0.0172 (5)	0.0160 (6)	−0.0041 (4)	0.0038 (4)	−0.0043 (4)
C3	0.0141 (5)	0.0197 (6)	0.0232 (6)	−0.0035 (4)	0.0029 (5)	−0.0050 (5)
O1	0.0168 (4)	0.0196 (4)	0.0213 (4)	−0.0088 (3)	0.0012 (3)	−0.0052 (3)
C4	0.0185 (6)	0.0260 (6)	0.0153 (6)	−0.0064 (5)	0.0011 (5)	−0.0064 (5)
C5	0.0145 (5)	0.0179 (6)	0.0185 (6)	−0.0014 (4)	0.0019 (4)	−0.0088 (5)

N1—C1	1.2971 (14)	C2—H2B	0.9900
N1—H11	0.916 (15)	C3—O1	1.4302 (14)
N2—C1	1.3595 (14)	C3—H3A	0.9900
N2—H21	0.901 (16)	C3—H3B	0.9900
N2—H22	0.881 (16)	O1—C4	1.4268 (14)
N3—C1	1.3902 (13)	C4—C5	1.5169 (16)
N3—C5	1.4602 (14)	C4—H4A	0.9900
N3—C2	1.4671 (14)	C4—H4B	0.9900
C2—C3	1.5081 (16)	C5—H5A	0.9900
C2—H2A	0.9900	C5—H5B	0.9900
C1—N1—H11	107.8 (9)	C2—C3—H3A	109.5
C1—N2—H21	114.6 (10)	O1—C3—H3B	109.5
C1—N2—H22	119.6 (10)	C2—C3—H3B	109.5
H21—N2—H22	120.8 (14)	H3A—C3—H3B	108.1
C1—N3—C5	117.47 (9)	C4—O1—C3	109.61 (9)
C1—N3—C2	119.85 (9)	O1—C4—C5	111.87 (9)
C5—N3—C2	111.60 (9)	O1—C4—H4A	109.2
N1—C1—N2	124.83 (10)	C5—C4—H4A	109.2
N1—C1—N3	119.68 (10)	O1—C4—H4B	109.2
N2—C1—N3	115.49 (9)	C5—C4—H4B	109.2
N3—C2—C3	109.19 (9)	H4A—C4—H4B	107.9
N3—C2—H2A	109.8	N3—C5—C4	109.27 (9)
C3—C2—H2A	109.8	N3—C5—H5A	109.8
N3—C2—H2B	109.8	C4—C5—H5A	109.8
C3—C2—H2B	109.8	N3—C5—H5B	109.8
H2A—C2—H2B	108.3	C4—C5—H5B	109.8
O1—C3—C2	110.87 (9)	H5A—C5—H5B	108.3
O1—C3—H3A	109.5
C5—N3—C1—N1	−2.87 (16)	N3—C2—C3—O1	−58.69 (12)
C2—N3—C1—N1	−143.83 (11)	C2—C3—O1—C4	60.42 (12)
C5—N3—C1—N2	177.42 (10)	C3—O1—C4—C5	−59.34 (13)
C2—N3—C1—N2	36.46 (14)	C1—N3—C5—C4	161.31 (10)
C1—N3—C2—C3	−160.75 (10)	C2—N3—C5—C4	−54.67 (12)
C5—N3—C2—C3	56.20 (12)	O1—C4—C5—N3	56.31 (13)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H21···N1i	0.90 (2)	2.03 (2)	2.930 (1)	174 (1)
N2—H22···O1ii	0.88 (2)	2.13 (2)	3.007 (1)	174 (1)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H21⋯N1i	0.90 (2)	2.03 (2)	2.930 (1)	174 (1)
N2—H22⋯O1ii	0.88 (2)	2.13 (2)	3.007 (1)	174 (1)

Symmetry codes: (i) ; (ii) .