6-Amino-nicotinamide.

In the title compound, C(6)H(7)N(3)O, the amide group is rotated such that the carbonyl O atom is syn to the pyridine N atom, with an O-C-C-C torsion angle of -23.55 (18)°. The crystal packing involves four hydrogen bonds of the types N-H⋯N and N-H⋯O. Two separate centrosymmetric rings are formed using N-H⋯N and N-H⋯O hydrogen bonds that result in a ribbon of 6-aminonicotinamide molecules, joined by the amide and amine functional groups. The remaining two hydrogen bonds are used to generate a three-dimensional packing arrangement.

Related literature

For pharmacological activity, see: Street et al. (1997 ▶); Budihardjo et al. (2000 ▶). For structurally related compounds, see: Miwa et al. (1999 ▶); Li et al. (2011 ▶).

Experimental

Crystal data

C6H7N3O

M = 137.15

Monoclinic,

a = 14.3483 (6) Å

b = 4.8143 (2) Å

c = 9.6685 (4) Å

β = 99.215 (2)°

V = 659.25 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.1 mm−1

T = 173 K

0.27 × 0.25 × 0.2 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.974, T max = 0.980

4078 measured reflections

1582 independent reflections

1300 reflections with I > 2σ(I)

R int = 0.037

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.113

S = 1.03

1582 reflections

107 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.33 e Å−3

Δρmin = −0.21 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT-Plus (Bruker, 2004 ▶); data reduction: SAINT-Plus and XPREP (Bruker 2004 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812031224/fj2584sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812031224/fj2584Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812031224/fj2584Isup3.mol

Supplementary material file. DOI: 10.1107/S1600536812031224/fj2584Isup4.cml

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

C6H7N3O	F(000) = 288
Mr = 137.15	Dx = 1.382 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1574 reflections
a = 14.3483 (6) Å	θ = 2.9–28.4°
b = 4.8143 (2) Å	µ = 0.1 mm−1
c = 9.6685 (4) Å	T = 173 K
β = 99.215 (2)°	Cube, colourless
V = 659.25 (5) Å3	0.27 × 0.25 × 0.2 mm
Z = 4

Bruker APEXII CCD area-detector diffractometer	1300 reflections with I > 2σ(I)
ω scans	Rint = 0.037
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	θmax = 28°, θmin = 2.9°
Tmin = 0.974, Tmax = 0.980	h = −18→18
4078 measured reflections	k = −6→6
1582 independent reflections	l = −11→12

Refinement on F2	0 restraints
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.040	w = 1/[σ2(Fo2) + (0.0577P)2 + 0.1618P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.113	(Δ/σ)max < 0.001
S = 1.03	Δρmax = 0.33 e Å−3
1582 reflections	Δρmin = −0.21 e Å−3
107 parameters

Experimental. Absorption corrections were made using the program SADABS (Sheldrick, 1996)

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.

	x	y	z	Uiso*/Ueq
C1	0.21465 (8)	0.3830 (3)	0.06966 (12)	0.0216 (3)
C2	0.28897 (8)	0.3112 (3)	0.00180 (12)	0.0227 (3)
H2	0.279	0.1654	−0.0651	0.027*
C3	0.38732 (8)	0.6424 (2)	0.11660 (12)	0.0212 (3)
C4	0.31587 (9)	0.7304 (3)	0.19125 (13)	0.0246 (3)
H4	0.3271	0.878	0.257	0.03*
C5	0.22979 (9)	0.5994 (3)	0.16746 (13)	0.0242 (3)
H5	0.1808	0.6552	0.217	0.029*
C6	0.12477 (8)	0.2249 (3)	0.03728 (12)	0.0235 (3)
N1	0.06896 (8)	0.2202 (3)	0.13454 (12)	0.0315 (3)
H1S	0.0150 (13)	0.121 (3)	0.1119 (18)	0.037 (4)*
H1A	0.0869 (12)	0.292 (3)	0.219 (2)	0.036 (4)*
N2	0.37410 (7)	0.4326 (2)	0.02370 (11)	0.0232 (3)
N3	0.47474 (8)	0.7598 (2)	0.14074 (13)	0.0275 (3)
H3S	0.5162 (12)	0.710 (4)	0.0824 (19)	0.037 (4)*
H3A	0.4816 (12)	0.918 (3)	0.1855 (18)	0.034 (4)*
O1	0.10436 (6)	0.0996 (2)	−0.07631 (9)	0.0295 (3)

	U11	U22	U33	U12	U13	U23
C1	0.0207 (5)	0.0269 (6)	0.0175 (5)	−0.0015 (4)	0.0042 (4)	0.0035 (4)
C2	0.0232 (6)	0.0257 (6)	0.0194 (6)	−0.0029 (5)	0.0045 (4)	−0.0017 (5)
C3	0.0206 (6)	0.0219 (6)	0.0208 (6)	−0.0007 (4)	0.0027 (4)	0.0028 (4)
C4	0.0275 (6)	0.0239 (6)	0.0229 (6)	−0.0008 (5)	0.0058 (5)	−0.0034 (5)
C5	0.0234 (6)	0.0281 (6)	0.0223 (6)	0.0026 (5)	0.0078 (5)	0.0010 (5)
C6	0.0203 (6)	0.0320 (6)	0.0185 (6)	−0.0012 (5)	0.0039 (4)	0.0023 (5)
N1	0.0246 (6)	0.0497 (7)	0.0219 (6)	−0.0122 (5)	0.0086 (4)	−0.0067 (5)
N2	0.0219 (5)	0.0260 (5)	0.0224 (5)	−0.0017 (4)	0.0061 (4)	−0.0017 (4)
N3	0.0229 (6)	0.0275 (6)	0.0329 (6)	−0.0045 (4)	0.0068 (4)	−0.0066 (5)
O1	0.0250 (5)	0.0451 (6)	0.0190 (5)	−0.0094 (4)	0.0057 (3)	−0.0040 (4)

C1—C2	1.3824 (17)	C4—H4	0.95
C1—C5	1.4004 (17)	C5—H5	0.95
C1—C6	1.4870 (16)	C6—O1	1.2461 (15)
C2—N2	1.3401 (15)	C6—N1	1.3293 (16)
C2—H2	0.95	N1—H1S	0.907 (18)
C3—N2	1.3449 (15)	N1—H1A	0.888 (18)
C3—N3	1.3614 (15)	N3—H3S	0.915 (18)
C3—C4	1.4100 (17)	N3—H3A	0.875 (17)
C4—C5	1.3730 (17)
C2—C1—C5	117.29 (11)	C4—C5—H5	120.2
C2—C1—C6	118.75 (11)	C1—C5—H5	120.2
C5—C1—C6	123.95 (11)	O1—C6—N1	122.15 (12)
N2—C2—C1	124.66 (11)	O1—C6—C1	120.45 (11)
N2—C2—H2	117.7	N1—C6—C1	117.39 (11)
C1—C2—H2	117.7	C6—N1—H1S	115.2 (11)
N2—C3—N3	116.99 (11)	C6—N1—H1A	121.9 (11)
N2—C3—C4	122.08 (11)	H1S—N1—H1A	122.5 (16)
N3—C3—C4	120.87 (11)	C2—N2—C3	117.43 (10)
C5—C4—C3	118.99 (11)	C3—N3—H3S	117.2 (11)
C5—C4—H4	120.5	C3—N3—H3A	118.4 (11)
C3—C4—H4	120.5	H3S—N3—H3A	120.1 (15)
C4—C5—C1	119.53 (11)
C5—C1—C2—N2	0.43 (19)	C2—C1—C6—O1	−23.55 (18)
C6—C1—C2—N2	−178.45 (11)	C5—C1—C6—O1	157.66 (12)
N2—C3—C4—C5	−0.61 (19)	C2—C1—C6—N1	155.44 (12)
N3—C3—C4—C5	−177.58 (11)	C5—C1—C6—N1	−23.36 (18)
C3—C4—C5—C1	−0.24 (18)	C1—C2—N2—C3	−1.24 (18)
C2—C1—C5—C4	0.34 (18)	N3—C3—N2—C2	178.40 (11)
C6—C1—C5—C4	179.15 (11)	C4—C3—N2—C2	1.31 (18)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1i	0.888 (18)	2.021 (19)	2.8933 (15)	167.2 (15)
N1—H1S···O1ii	0.907 (18)	1.997 (19)	2.9024 (14)	176.0 (16)
N3—H3S···N2iii	0.915 (18)	2.125 (19)	3.0322 (15)	170.9 (15)
N3—H3A···N3iv	0.875 (17)	2.363 (17)	3.2083 (16)	162.7 (15)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O1i	0.888 (18)	2.021 (19)	2.8933 (15)	167.2 (15)
N1—H1S⋯O1ii	0.907 (18)	1.997 (19)	2.9024 (14)	176.0 (16)
N3—H3S⋯N2iii	0.915 (18)	2.125 (19)	3.0322 (15)	170.9 (15)
N3—H3A⋯N3iv	0.875 (17)	2.363 (17)	3.2083 (16)	162.7 (15)

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .