3-Amino-5-bromo-2-iodo-pyridine.

The reaction of 3-amino-5-bromo-pyridine with N-iodo-succinimide in the presence of acetic acid produces the title compound, C(5)H(4)BrIN, with an iodo substituent in position 2 of the pyridine ring. The crystal structure features rather weak inter-molecular N-H⋯N hydrogen bonds linking the mol-ecules into chains along the z axis of the crystal.

Related literature

For structures of ortho-iodo­anilines, see: McWilliam et al. (2001 ▶); Sandor & Foxman (2000 ▶); Parkin et al. (2005 ▶).

Experimental

Crystal data

C5H4BrIN2

M = 298.90

Monoclinic,

a = 4.0983 (12) Å

b = 15.172 (4) Å

c = 12.038 (3) Å

β = 90.152 (5)°

V = 748.5 (3) Å3

Z = 4

Mo Kα radiation

μ = 9.53 mm−1

T = 100 (2) K

0.40 × 0.33 × 0.04 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.234, T max = 0.557

3783 measured reflections

1251 independent reflections

1086 reflections with I > 2σ(I)

R int = 0.037

Refinement

R[F 2 > 2σ(F 2)] = 0.032

wR(F 2) = 0.082

S = 1.05

1251 reflections

82 parameters

H-atom parameters constrained

Δρmax = 1.33 e Å−3

Δρmin = −0.92 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808040452/rz2275sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808040452/rz2275Isup2.hkl

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

C5H4BrIN2	F(000) = 544
Mr = 298.90	Dx = 2.652 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2536 reflections
a = 4.0983 (12) Å	θ = 2.7–25.3°
b = 15.172 (4) Å	µ = 9.53 mm−1
c = 12.038 (3) Å	T = 100 K
β = 90.152 (5)°	Plate, colourless
V = 748.5 (3) Å3	0.40 × 0.33 × 0.04 mm
Z = 4

Bruker APEXII CCD diffractometer	1251 independent reflections
Radiation source: fine-focus sealed tube	1086 reflections with I > 2σ(I)
graphite	Rint = 0.037
φ and ω scans	θmax = 25.3°, θmin = 2.2°
Absorption correction: analytical (SADABS; Bruker, 2001)	h = −4→1
Tmin = 0.234, Tmax = 0.557	k = −17→18
3783 measured reflections	l = −10→14

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)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.082	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.037P)2 + 2.524P] where P = (Fo2 + 2Fc2)/3
1251 reflections	(Δ/σ)max = 0.003
82 parameters	Δρmax = 1.33 e Å−3
0 restraints	Δρmin = −0.92 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
I1	0.18405 (10)	0.37509 (3)	0.48761 (3)	0.02516 (17)
Br1	−0.56202 (16)	0.01782 (4)	0.28399 (5)	0.0266 (2)
N2	−0.0278 (15)	0.3306 (4)	0.2326 (4)	0.0298 (13)
H2A	−0.0808	0.3282	0.1617	0.036*
H2B	0.0760	0.3769	0.2589	0.036*
N1	−0.1133 (14)	0.1994 (4)	0.4858 (4)	0.0264 (13)
C2	−0.2684 (18)	0.1278 (4)	0.4470 (6)	0.0264 (15)
H2	−0.3243	0.0815	0.4965	0.032*
C1	−0.0390 (15)	0.2637 (5)	0.4165 (5)	0.0242 (14)
C5	−0.1071 (15)	0.2622 (5)	0.3019 (5)	0.0227 (14)
C3	−0.3480 (16)	0.1208 (4)	0.3350 (5)	0.0221 (14)
C4	−0.2713 (15)	0.1878 (4)	0.2636 (5)	0.0213 (14)
H4	−0.3303	0.1834	0.1874	0.026*

	U11	U22	U33	U12	U13	U23
I1	0.0244 (3)	0.0324 (3)	0.0187 (3)	−0.00094 (16)	−0.00522 (18)	−0.00340 (17)
Br1	0.0285 (4)	0.0274 (4)	0.0238 (4)	−0.0007 (3)	−0.0039 (3)	−0.0027 (3)
N2	0.044 (4)	0.029 (3)	0.016 (3)	−0.002 (3)	−0.008 (3)	−0.001 (2)
N1	0.035 (3)	0.030 (3)	0.015 (3)	0.002 (2)	−0.005 (2)	0.002 (2)
C2	0.035 (4)	0.024 (4)	0.020 (3)	0.000 (3)	−0.007 (3)	0.002 (3)
C1	0.017 (3)	0.036 (4)	0.020 (3)	0.004 (3)	−0.006 (3)	−0.008 (3)
C5	0.017 (3)	0.035 (4)	0.016 (3)	0.006 (3)	−0.001 (2)	−0.002 (3)
C3	0.021 (4)	0.027 (4)	0.018 (3)	0.005 (3)	−0.001 (3)	−0.001 (3)
C4	0.021 (3)	0.033 (4)	0.011 (3)	0.007 (3)	−0.005 (2)	−0.006 (3)

I1—C1	2.102 (7)	C2—C3	1.390 (9)
Br1—C3	1.894 (7)	C2—H2	0.9500
N2—C5	1.371 (9)	C1—C5	1.407 (9)
N2—H2A	0.8800	C5—C4	1.393 (9)
N2—H2B	0.8800	C3—C4	1.368 (9)
N1—C1	1.320 (9)	C4—H4	0.9500
N1—C2	1.342 (9)
C5—N2—H2A	120.0	N2—C5—C4	121.8 (5)
C5—N2—H2B	120.0	N2—C5—C1	122.6 (6)
H2A—N2—H2B	120.0	C4—C5—C1	115.6 (6)
C1—N1—C2	119.3 (5)	C4—C3—C2	119.9 (6)
N1—C2—C3	120.6 (6)	C4—C3—Br1	121.1 (5)
N1—C2—H2	119.7	C2—C3—Br1	119.0 (5)
C3—C2—H2	119.7	C3—C4—C5	120.4 (6)
N1—C1—C5	124.2 (6)	C3—C4—H4	119.8
N1—C1—I1	116.0 (4)	C5—C4—H4	119.8
C5—C1—I1	119.8 (5)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···N1i	0.88	2.16	3.025 (8)	166
N2—H2B···I1	0.88	2.79	3.259 (5)	115

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯N1i	0.88	2.16	3.025 (8)	166
N2—H2B⋯I1	0.88	2.79	3.259 (5)	115

Symmetry code: (i) .