N-(6-Bromo­pyridin-2-yl)pyridin-2-amine

In the title compound, C₁₀H₈BrN₃, the dihedral angle between the pyridine ring planes is 6.10 (15)°. In the crystal structure, the mol­ecules are linked by N—H...N hydrogen bonds, leading to chains.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.032
• wR factor = 0.086
• Data-to-parameter ratio = 13.6

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.90

Alert level G
ABSTM02_ALERT_3_G  When printed, the submitted absorption T values will be
            replaced by the scaled T values. Since the ratio of scaled T's
            is identical to the ratio of reported T values, the scaling
            does not imply a change to the absorption corrections used in
            the study.
            Ratio of Tmax expected/reported      0.897
            Tmax scaled      0.451 Tmin scaled      0.337

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   1 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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S1. Comment

Here we report the structure of the title compound, (I), which arose as an unexpected product from attempts to prepare a coordination polymer containing zinc(II) ions and N-(6-bromopyridin-2-yl)pyridin-2-amine (tpdaH₂Br) (Xu et al., 2004).

The dihedral angle between the pyridine ring planes is 6.10 (15)°. (Fig. 1). In the crystal, molecules are linked by N—H···N hydrogen bonds (Table 1) to result in infinite chains.

Related literature

For background, see: Xu et al. (2004).

S2. Experimental

ZnSO₄ (0.016 g, 0.01 mmol), tpdaH₂Br (0.022 g, 0.011 mmol) and NaOH (0.0012 g, 0.003 mmol), were refluxed in acetonitrile for six hours with stirring. The resultant liquor was filtered to give a clear solution which was infiltrated by diethyl ether in a closed vessel. After two weeks, colourless blocks of (I) were recovered.

S3. Refinement

The H atoms were placed in calculated positions (C—H = 0.93 Å, N—H = 0.86 Å) and refined as riding, with U_iso(H) = 1.2U_eq(carrier).

Computing details

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2004); software used to prepare material for publication: SHELXTL (Bruker, 2004).

Figures

Fig. 1. The molecular structure of (I), showing 50% probability displacement ellipsoids for the non-hydrogen atoms.

N-(6-Bromopyridin-2-yl)pyridin-2-amine

Crystal data

C10H8BrN3	F(000) = 992
Mr = 250.10	Dx = 1.710 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 1723 reflections
a = 22.177 (7) Å	θ = 2.0–25.2°
b = 7.551 (2) Å	µ = 4.19 mm^−1
c = 12.293 (4) Å	T = 298 K
β = 109.299 (4)°	Block, colourless
V = 1942.9 (10) Å^3	0.29 × 0.25 × 0.19 mm
Z = 8

Data collection

Bruker APEXII CCD diffractometer	1723 independent reflections
Radiation source: fine-focus sealed tube	1403 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.074
Detector resolution: 0 pixels mm^-1	θmax = 25.2°, θmin = 2.0°
φ and ω scans	h = −26→26
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	k = −8→9
Tmin = 0.376, Tmax = 0.503	l = −14→14
5705 measured reflections

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)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.087	H-atom parameters constrained
S = 1.06	w = 1/[σ^2(Fo^2) + (0.0456P)^2] where P = (Fo^2 + 2Fc^2)/3
1723 reflections	(Δ/σ)max < 0.001
127 parameters	Δρmax = 0.31 e Å^−3
0 restraints	Δρmin = −0.45 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
Br1	0.348533 (14)	0.03734 (6)	0.56958 (3)	0.06353 (18)
C1	0.41493 (12)	0.1357 (4)	0.5224 (2)	0.0404 (6)
C2	0.41213 (13)	0.1193 (4)	0.4089 (2)	0.0450 (7)
H2	0.3782	0.0637	0.3537	0.054*
C3	0.46233 (13)	0.1898 (4)	0.3832 (2)	0.0475 (7)
H3	0.4623	0.1853	0.3076	0.057*
C4	0.51341 (13)	0.2679 (4)	0.4666 (2)	0.0431 (7)
H4	0.5476	0.3156	0.4485	0.052*
C5	0.51153 (11)	0.2723 (4)	0.5782 (2)	0.0367 (6)
C6	0.61548 (12)	0.4275 (4)	0.6853 (2)	0.0381 (6)
C7	0.64667 (14)	0.5036 (4)	0.7932 (2)	0.0449 (7)
H7	0.6301	0.4932	0.8533	0.054*
C8	0.69133 (15)	0.5299 (4)	0.6151 (3)	0.0526 (8)
H8	0.7069	0.5397	0.5538	0.063*
C9	0.72529 (13)	0.6080 (5)	0.7165 (3)	0.0525 (8)
H9	0.7629	0.6692	0.7241	0.063*
C10	0.70248 (13)	0.5941 (5)	0.8077 (3)	0.0510 (8)
H10	0.7247	0.6455	0.8784	0.061*
N1	0.46154 (9)	0.2106 (3)	0.60504 (16)	0.0381 (5)
N2	0.63662 (11)	0.4391 (3)	0.5976 (2)	0.0465 (6)
N3	0.55897 (10)	0.3372 (3)	0.67403 (17)	0.0438 (6)
H3A	0.5523	0.3185	0.7382	0.053*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.0490 (2)	0.0850 (3)	0.0585 (3)	−0.02186 (15)	0.02024 (17)	−0.00919 (16)
C1	0.0378 (13)	0.0412 (18)	0.0436 (15)	0.0047 (12)	0.0153 (12)	0.0020 (12)
C2	0.0442 (15)	0.0518 (19)	0.0350 (14)	0.0043 (13)	0.0077 (12)	−0.0079 (13)
C3	0.0497 (16)	0.062 (2)	0.0308 (13)	0.0095 (14)	0.0126 (12)	−0.0004 (13)
C4	0.0457 (14)	0.0493 (19)	0.0388 (14)	0.0059 (12)	0.0200 (13)	0.0036 (13)
C5	0.0344 (13)	0.0395 (16)	0.0353 (13)	0.0053 (11)	0.0103 (11)	0.0022 (12)
C6	0.0332 (13)	0.0424 (18)	0.0376 (14)	0.0059 (11)	0.0103 (11)	0.0052 (12)
C7	0.0426 (15)	0.053 (2)	0.0386 (15)	0.0000 (12)	0.0128 (13)	0.0025 (13)
C8	0.0430 (16)	0.070 (2)	0.0493 (17)	−0.0016 (14)	0.0218 (14)	0.0038 (16)
C9	0.0371 (14)	0.058 (2)	0.0602 (19)	−0.0044 (14)	0.0131 (14)	0.0058 (16)
C10	0.0442 (16)	0.056 (2)	0.0454 (16)	−0.0016 (14)	0.0054 (13)	−0.0014 (14)
N1	0.0370 (11)	0.0448 (14)	0.0325 (11)	0.0009 (10)	0.0113 (9)	−0.0016 (10)
N2	0.0411 (13)	0.0582 (19)	0.0439 (13)	−0.0025 (11)	0.0189 (11)	−0.0007 (11)
N3	0.0394 (11)	0.0616 (18)	0.0312 (11)	−0.0077 (11)	0.0126 (10)	0.0019 (10)

Geometric parameters (Å, º)

Br1—C1	1.903 (3)	C6—N3	1.392 (3)
C1—N1	1.314 (3)	C6—C7	1.401 (4)
C1—C2	1.381 (4)	C7—C10	1.373 (4)
C2—C3	1.362 (4)	C7—H7	0.9300
C2—H2	0.9300	C8—N2	1.348 (4)
C3—C4	1.384 (4)	C8—C9	1.359 (5)
C3—H3	0.9300	C8—H8	0.9300
C4—C5	1.387 (4)	C9—C10	1.378 (4)
C4—H4	0.9300	C9—H9	0.9300
C5—N1	1.340 (3)	C10—H10	0.9300
C5—N3	1.384 (3)	N3—H3A	0.8600
C6—N2	1.313 (4)
N1—C1—C2	125.5 (3)	C10—C7—C6	117.9 (3)
N1—C1—Br1	115.00 (19)	C10—C7—H7	121.0
C2—C1—Br1	119.5 (2)	C6—C7—H7	121.0
C3—C2—C1	115.6 (3)	N2—C8—C9	124.3 (3)
C3—C2—H2	122.2	N2—C8—H8	117.8
C1—C2—H2	122.2	C9—C8—H8	117.8
C2—C3—C4	121.8 (3)	C8—C9—C10	118.1 (3)
C2—C3—H3	119.1	C8—C9—H9	120.9
C4—C3—H3	119.1	C10—C9—H9	120.9
C3—C4—C5	117.3 (3)	C7—C10—C9	119.4 (3)
C3—C4—H4	121.4	C7—C10—H10	120.3
C5—C4—H4	121.4	C9—C10—H10	120.3
N1—C5—N3	111.8 (2)	C1—N1—C5	117.6 (2)
N1—C5—C4	122.2 (2)	C6—N2—C8	116.7 (2)
N3—C5—C4	126.0 (2)	C5—N3—C6	131.6 (2)
N2—C6—N3	120.3 (2)	C5—N3—H3A	114.2
N2—C6—C7	123.5 (3)	C6—N3—H3A	114.2
N3—C6—C7	116.2 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···N1^i	0.86	2.21	3.052 (3)	168

Symmetry code: (i) −x+1, y, −z+3/2.