5-Bromo-3-(indan-1-yl-oxy)pyridin-2-amine.

The title compound, C(14)H(13)BrN(2)O, was obtained by reaction of indan-1-yl methane-sulfonate with 2-amino-5-bromo-pyridin-3-ol in the presence of caesium carbonate. The indane ring system is approximately planar [all but one of the C atoms are coplanar within 0.03 Å, the latter atom being displaced by 0.206 (2) Å from the mean plane through the remaining atoms] and forms a dihedral angle of 58.41 (4)° with the pyridine ring. In the crystal, centrosymmetrically related mol-ecules are linked into dimers by N-H⋯N hydrogen bonds.

Related literature

For related structures with an indane group linked to a pyridine derivative through a C—O—C bridge, see: Dinçer et al. (2004 ▶); Lifshits et al. (2008 ▶).

Experimental

Crystal data

C14H13BrN2O

M = 305.17

Monoclinic,

a = 11.3944 (18) Å

b = 9.4515 (15) Å

c = 12.438 (2) Å

β = 110.678 (2)°

V = 1253.2 (3) Å3

Z = 4

Mo Kα radiation

μ = 3.27 mm−1

T = 100 K

0.21 × 0.16 × 0.08 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.547, T max = 0.780

23669 measured reflections

2942 independent reflections

2595 reflections with I > 2σ(I)

R int = 0.046

Refinement

R[F 2 > 2σ(F 2)] = 0.023

wR(F 2) = 0.054

S = 1.03

2942 reflections

163 parameters

H-atom parameters constrained

Δρmax = 0.38 e Å−3

Δρmin = −0.30 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/S1600536811005332/rz2555sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811005332/rz2555Isup2.hkl

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

C14H13BrN2O	F(000) = 616
Mr = 305.17	Dx = 1.617 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 9797 reflections
a = 11.3944 (18) Å	θ = 2.8–27.7°
b = 9.4515 (15) Å	µ = 3.27 mm−1
c = 12.438 (2) Å	T = 100 K
β = 110.678 (2)°	Block, colorless
V = 1253.2 (3) Å3	0.21 × 0.16 × 0.08 mm
Z = 4

Bruker APEXII CCD diffractometer	2942 independent reflections
Radiation source: fine-focus sealed tube	2595 reflections with I > 2σ(I)
graphite	Rint = 0.046
φ and ω scans	θmax = 28.3°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −15→14
Tmin = 0.547, Tmax = 0.780	k = −12→12
23669 measured reflections	l = −16→15

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)] = 0.023	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.054	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0191P)2 + 0.7815P] where P = (Fo2 + 2Fc2)/3
2942 reflections	(Δ/σ)max = 0.001
163 parameters	Δρmax = 0.38 e Å−3
0 restraints	Δρmin = −0.30 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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
Br1	1.235622 (16)	1.080477 (17)	1.070416 (15)	0.02063 (6)
O1	0.95752 (11)	0.77404 (12)	0.71352 (10)	0.0192 (3)
N1	1.06647 (13)	0.68706 (14)	1.01301 (12)	0.0179 (3)
N2	0.95112 (15)	0.56292 (15)	0.84811 (13)	0.0227 (3)
H2NA	0.9477	0.4894	0.8903	0.027*
H2NB	0.9150	0.5591	0.7729	0.027*
C1	1.01219 (16)	0.68247 (17)	0.89913 (14)	0.0163 (3)
C2	1.01793 (15)	0.79884 (17)	0.82822 (14)	0.0165 (3)
C3	1.08206 (16)	0.91835 (17)	0.87805 (15)	0.0171 (3)
H3	1.0868	0.9979	0.8331	0.020*
C4	1.14048 (16)	0.91900 (16)	0.99797 (15)	0.0161 (3)
C5	1.13089 (16)	0.80499 (17)	1.06228 (15)	0.0180 (3)
H5	1.1704	0.8086	1.1435	0.022*
C6	0.95743 (16)	0.88611 (17)	0.63483 (14)	0.0168 (3)
H6	1.0431	0.9283	0.6559	0.020*
C7	0.85977 (17)	1.00246 (18)	0.62819 (15)	0.0209 (4)
H7A	0.8003	0.9696	0.6647	0.025*
H7B	0.9019	1.0892	0.6681	0.025*
C8	0.78992 (16)	1.03247 (17)	0.49914 (15)	0.0184 (3)
H8A	0.6983	1.0385	0.4815	0.022*
H8B	0.8193	1.1220	0.4759	0.022*
C9	0.82218 (16)	0.90756 (16)	0.43914 (15)	0.0164 (3)
C10	0.91601 (15)	0.82524 (17)	0.51553 (14)	0.0163 (3)
C11	0.96492 (16)	0.70772 (17)	0.47841 (15)	0.0200 (4)
H11	1.0284	0.6517	0.5316	0.024*
C12	0.91930 (17)	0.67388 (18)	0.36230 (16)	0.0225 (4)
H12	0.9523	0.5947	0.3353	0.027*
C13	0.82497 (17)	0.75614 (19)	0.28514 (15)	0.0224 (4)
H13	0.7942	0.7322	0.2059	0.027*
C14	0.77560 (17)	0.87233 (18)	0.32274 (15)	0.0204 (4)
H14	0.7109	0.9272	0.2699	0.025*

	U11	U22	U33	U12	U13	U23
Br1	0.02147 (10)	0.01833 (9)	0.01970 (10)	−0.00397 (7)	0.00432 (7)	−0.00082 (6)
O1	0.0247 (7)	0.0182 (6)	0.0125 (6)	−0.0039 (5)	0.0038 (5)	0.0033 (4)
N1	0.0195 (7)	0.0179 (7)	0.0156 (7)	−0.0011 (6)	0.0055 (6)	0.0024 (5)
N2	0.0298 (9)	0.0198 (7)	0.0140 (7)	−0.0074 (6)	0.0021 (6)	0.0035 (6)
C1	0.0150 (8)	0.0174 (7)	0.0168 (8)	0.0007 (6)	0.0058 (7)	0.0029 (6)
C2	0.0149 (8)	0.0209 (8)	0.0137 (8)	0.0019 (6)	0.0052 (6)	0.0030 (6)
C3	0.0178 (8)	0.0168 (8)	0.0172 (9)	0.0013 (6)	0.0070 (7)	0.0039 (6)
C4	0.0141 (8)	0.0155 (7)	0.0184 (8)	−0.0002 (6)	0.0053 (7)	−0.0013 (6)
C5	0.0187 (9)	0.0201 (8)	0.0145 (8)	0.0009 (7)	0.0049 (7)	0.0003 (6)
C6	0.0195 (9)	0.0169 (7)	0.0140 (8)	−0.0022 (6)	0.0057 (7)	0.0033 (6)
C7	0.0257 (10)	0.0202 (8)	0.0161 (9)	0.0025 (7)	0.0067 (7)	0.0009 (7)
C8	0.0184 (9)	0.0171 (8)	0.0180 (9)	0.0002 (6)	0.0045 (7)	0.0020 (6)
C9	0.0170 (8)	0.0158 (7)	0.0166 (8)	−0.0037 (6)	0.0062 (7)	0.0018 (6)
C10	0.0159 (8)	0.0177 (8)	0.0158 (8)	−0.0032 (6)	0.0061 (7)	0.0012 (6)
C11	0.0179 (9)	0.0193 (8)	0.0225 (9)	−0.0002 (7)	0.0067 (7)	0.0013 (7)
C12	0.0233 (9)	0.0200 (8)	0.0262 (10)	−0.0048 (7)	0.0113 (8)	−0.0068 (7)
C13	0.0256 (10)	0.0258 (9)	0.0154 (9)	−0.0086 (7)	0.0066 (7)	−0.0050 (7)
C14	0.0213 (9)	0.0199 (8)	0.0169 (9)	−0.0040 (7)	0.0028 (7)	0.0029 (7)

Br1—C4	1.9044 (16)	C7—C8	1.545 (2)
O1—C2	1.368 (2)	C7—H7A	0.9900
O1—C6	1.4419 (19)	C7—H7B	0.9900
N1—C1	1.331 (2)	C8—C9	1.510 (2)
N1—C5	1.356 (2)	C8—H8A	0.9900
N2—C1	1.361 (2)	C8—H8B	0.9900
N2—H2NA	0.8800	C9—C10	1.391 (2)
N2—H2NB	0.8800	C9—C14	1.395 (2)
C1—C2	1.426 (2)	C10—C11	1.393 (2)
C2—C3	1.369 (2)	C11—C12	1.388 (3)
C3—C4	1.402 (2)	C11—H11	0.9500
C3—H3	0.9500	C12—C13	1.397 (3)
C4—C5	1.369 (2)	C12—H12	0.9500
C5—H5	0.9500	C13—C14	1.388 (3)
C6—C10	1.504 (2)	C13—H13	0.9500
C6—C7	1.546 (2)	C14—H14	0.9500
C6—H6	1.0000
C2—O1—C6	117.49 (13)	C6—C7—H7A	110.4
C1—N1—C5	118.79 (14)	C8—C7—H7B	110.4
C1—N2—H2NA	120.0	C6—C7—H7B	110.4
C1—N2—H2NB	120.0	H7A—C7—H7B	108.6
H2NA—N2—H2NB	120.0	C9—C8—C7	104.11 (13)
N1—C1—N2	119.49 (15)	C9—C8—H8A	110.9
N1—C1—C2	121.84 (15)	C7—C8—H8A	110.9
N2—C1—C2	118.66 (15)	C9—C8—H8B	110.9
O1—C2—C3	127.25 (15)	C7—C8—H8B	110.9
O1—C2—C1	113.39 (14)	H8A—C8—H8B	109.0
C3—C2—C1	119.35 (15)	C10—C9—C14	119.63 (16)
C2—C3—C4	117.53 (15)	C10—C9—C8	111.25 (15)
C2—C3—H3	121.2	C14—C9—C8	129.04 (16)
C4—C3—H3	121.2	C9—C10—C11	121.40 (16)
C5—C4—C3	120.80 (15)	C9—C10—C6	110.97 (14)
C5—C4—Br1	120.25 (13)	C11—C10—C6	127.55 (15)
C3—C4—Br1	118.94 (12)	C12—C11—C10	118.81 (16)
N1—C5—C4	121.67 (16)	C12—C11—H11	120.6
N1—C5—H5	119.2	C10—C11—H11	120.6
C4—C5—H5	119.2	C11—C12—C13	120.06 (16)
O1—C6—C10	108.27 (13)	C11—C12—H12	120.0
O1—C6—C7	112.76 (14)	C13—C12—H12	120.0
C10—C6—C7	104.49 (14)	C14—C13—C12	120.92 (16)
O1—C6—H6	110.4	C14—C13—H13	119.5
C10—C6—H6	110.4	C12—C13—H13	119.5
C7—C6—H6	110.4	C13—C14—C9	119.18 (16)
C8—C7—C6	106.45 (14)	C13—C14—H14	120.4
C8—C7—H7A	110.4	C9—C14—H14	120.4

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2NA···N1i	0.88	2.10	2.975 (2)	178

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2NA⋯N1i	0.88	2.10	2.975 (2)	178

Symmetry code: (i) .