6-Bromo-1,3-bis-[(1,3-dioxolan-2-yl)meth-yl]-1H-imidazo[4,5-b]pyridin-2(3H)-one.

In the title compound, C14H16BrN3O5, the N atoms adjacent to the carbonyl group in the five-membered ring are substituted by (1,3-dioxolan-2-yl)methyl groups. The fused ring system is essentially planar, with the largest deviation from the mean plane being 0.014 (2) Å for the C atom bearing the Br atom. The first oxolane ring, attached on the side of the N atom belonging to the pyridine ring, has an envelope conformation with one of the O atoms as the flap, whereas the second oxolane ring displays a twisted boat conformation. The two oxolane rings display envelope and twisted boat conformations. In the crystal, mol-ecules are linked by C-H⋯O hydrogen bonds, building chains parallel to the a-axis direction.

Related literature

For the biological activity of imidazo­pyridine derivatives, see: Temple et al. (1987 ▶); Barraclough et al. (1990 ▶); Janssens et al. (1985 ▶); Liu et al. (2008 ▶); Bavetsias et al. (2010 ▶); Coates et al. (1993 ▶); For the chemistry of synthetic dyes, see: Ryabukhin et al. (2006 ▶); Schiffmann et al. (2006 ▶).

Experimental

Crystal data

C14H16BrN3O5

M = 386.21

Monoclinic,

a = 5.1144 (1) Å

b = 17.8029 (4) Å

c = 16.5365 (5) Å

β = 97.009 (2)°

V = 1494.42 (6) Å3

Z = 4

Mo Kα radiation

μ = 2.78 mm−1

T = 296 K

0.15 × 0.07 × 0.02 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.674, T max = 0.936

13392 measured reflections

3421 independent reflections

2632 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.089

S = 1.02

3421 reflections

208 parameters

H-atom parameters constrained

Δρmax = 0.45 e Å−3

Δρmin = −0.27 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: APEX2; data reduction: SAINT (Bruker, 2009 ▶); 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, 2012 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶) and publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813014591/fj2631sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813014591/fj2631Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813014591/fj2631Isup3.cml

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

C14H16BrN3O5	F(000) = 784
Mr = 386.21	Dx = 1.717 Mg m−3
Monoclinic, P21/n	Melting point: 446 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 5.1144 (1) Å	Cell parameters from 4379 reflections
b = 17.8029 (4) Å	θ = 2.3–25.5°
c = 16.5365 (5) Å	µ = 2.78 mm−1
β = 97.009 (2)°	T = 296 K
V = 1494.42 (6) Å3	Needle, white
Z = 4	0.15 × 0.07 × 0.02 mm

Bruker APEXII CCD diffractometer	3421 independent reflections
Radiation source: microfocus source	2632 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.027
φ and ω scans	θmax = 27.5°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −6→5
Tmin = 0.674, Tmax = 0.936	k = −23→23
13392 measured reflections	l = −21→20

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)] = 0.035	Hydrogen site location: difference Fourier map
wR(F2) = 0.089	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0418P)2 + 0.7351P] where P = (Fo2 + 2Fc2)/3
3421 reflections	(Δ/σ)max = 0.010
208 parameters	Δρmax = 0.45 e Å−3
0 restraints	Δρmin = −0.27 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 > 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
Br1	1.05083 (6)	0.395344 (15)	0.301591 (18)	0.05380 (12)
C1	0.8031 (5)	0.32618 (13)	0.33438 (15)	0.0401 (5)
C2	0.7746 (5)	0.32059 (13)	0.41724 (15)	0.0412 (5)
H2	0.8760	0.3485	0.4570	0.049*
C3	0.5856 (5)	0.27082 (12)	0.43522 (14)	0.0371 (5)
C4	0.4416 (5)	0.23061 (12)	0.37221 (14)	0.0360 (5)
C5	0.6557 (5)	0.28362 (13)	0.27657 (15)	0.0419 (6)
H5	0.6855	0.2890	0.2225	0.050*
C6	0.2946 (5)	0.19654 (13)	0.49010 (15)	0.0411 (6)
C7	0.6085 (5)	0.26864 (15)	0.58864 (15)	0.0465 (6)
H7A	0.7984	0.2710	0.5898	0.056*
H7B	0.5692	0.2289	0.6254	0.056*
C8	0.5135 (5)	0.34154 (15)	0.61902 (15)	0.0444 (6)
H8	0.6117	0.3526	0.6723	0.053*
C9	0.3556 (7)	0.45586 (17)	0.5782 (2)	0.0689 (9)
H9A	0.2573	0.4709	0.5269	0.083*
H9B	0.4373	0.5000	0.6049	0.083*
C10	0.1799 (6)	0.41836 (17)	0.6312 (2)	0.0583 (7)
H10A	0.2136	0.4365	0.6868	0.070*
H10B	−0.0039	0.4269	0.6111	0.070*
C11	0.0926 (5)	0.13044 (14)	0.36364 (16)	0.0432 (6)
H11A	−0.0073	0.1535	0.3165	0.052*
H11B	−0.0310	0.1123	0.3992	0.052*
C12	0.2506 (5)	0.06459 (13)	0.33618 (16)	0.0444 (6)
H12	0.3725	0.0829	0.2993	0.053*
C13	0.2579 (7)	−0.03685 (19)	0.4183 (2)	0.0718 (10)
H13A	0.1987	−0.0342	0.4718	0.086*
H13B	0.3727	−0.0801	0.4169	0.086*
C14	0.0312 (6)	−0.04352 (16)	0.35507 (17)	0.0545 (7)
H14A	0.0209	−0.0936	0.3318	0.065*
H14B	−0.1320	−0.0327	0.3771	0.065*
N1	0.4701 (4)	0.23447 (11)	0.29392 (12)	0.0411 (5)
N2	0.4931 (4)	0.24938 (11)	0.50679 (12)	0.0406 (5)
N3	0.2652 (4)	0.18604 (10)	0.40653 (12)	0.0395 (5)
O1	0.1709 (4)	0.16624 (10)	0.53895 (11)	0.0539 (5)
O2	0.5490 (4)	0.40116 (10)	0.56540 (12)	0.0518 (5)
O3	0.2459 (4)	0.34071 (11)	0.62657 (12)	0.0572 (5)
O4	0.3926 (4)	0.02910 (10)	0.40233 (13)	0.0639 (6)
O5	0.0812 (4)	0.01107 (10)	0.29556 (11)	0.0549 (5)

	U11	U22	U33	U12	U13	U23
Br1	0.04950 (18)	0.04746 (16)	0.0682 (2)	−0.00250 (12)	0.02211 (14)	0.00902 (13)
C1	0.0395 (13)	0.0352 (12)	0.0480 (14)	0.0052 (10)	0.0156 (11)	0.0052 (10)
C2	0.0402 (13)	0.0381 (12)	0.0456 (14)	−0.0001 (10)	0.0061 (11)	−0.0009 (10)
C3	0.0411 (13)	0.0345 (11)	0.0371 (12)	0.0033 (10)	0.0110 (10)	0.0028 (9)
C4	0.0382 (13)	0.0285 (10)	0.0421 (13)	0.0040 (9)	0.0083 (10)	0.0012 (9)
C5	0.0507 (15)	0.0361 (12)	0.0413 (13)	0.0077 (11)	0.0154 (11)	0.0031 (10)
C6	0.0449 (14)	0.0343 (12)	0.0451 (14)	0.0067 (10)	0.0096 (11)	0.0049 (10)
C7	0.0487 (15)	0.0517 (14)	0.0390 (13)	0.0017 (12)	0.0047 (11)	0.0042 (11)
C8	0.0449 (15)	0.0550 (15)	0.0328 (13)	−0.0039 (12)	0.0031 (11)	−0.0012 (11)
C9	0.063 (2)	0.0536 (17)	0.092 (2)	0.0057 (15)	0.0180 (18)	0.0063 (16)
C10	0.0472 (16)	0.0575 (16)	0.071 (2)	−0.0025 (13)	0.0103 (14)	−0.0145 (15)
C11	0.0407 (14)	0.0414 (12)	0.0466 (14)	−0.0022 (11)	0.0016 (11)	0.0035 (11)
C12	0.0479 (15)	0.0362 (12)	0.0474 (14)	−0.0016 (11)	−0.0010 (12)	0.0002 (11)
C13	0.080 (2)	0.065 (2)	0.066 (2)	−0.0116 (17)	−0.0120 (18)	0.0195 (16)
C14	0.0622 (18)	0.0474 (15)	0.0531 (17)	−0.0086 (13)	0.0031 (14)	0.0015 (12)
N1	0.0492 (12)	0.0361 (10)	0.0391 (11)	0.0042 (9)	0.0094 (9)	0.0013 (8)
N2	0.0464 (12)	0.0389 (10)	0.0377 (11)	−0.0022 (9)	0.0093 (9)	0.0011 (9)
N3	0.0444 (12)	0.0328 (10)	0.0428 (11)	−0.0015 (9)	0.0110 (9)	0.0006 (8)
O1	0.0597 (12)	0.0524 (11)	0.0531 (11)	−0.0068 (9)	0.0206 (9)	0.0100 (9)
O2	0.0510 (11)	0.0498 (10)	0.0568 (11)	−0.0021 (8)	0.0158 (9)	0.0048 (9)
O3	0.0526 (12)	0.0514 (11)	0.0719 (13)	−0.0062 (9)	0.0248 (10)	−0.0048 (9)
O4	0.0615 (13)	0.0453 (10)	0.0764 (14)	0.0050 (9)	−0.0258 (11)	0.0006 (10)
O5	0.0716 (14)	0.0457 (10)	0.0431 (10)	−0.0086 (9)	−0.0105 (9)	−0.0016 (8)

Br1—C1	1.893 (2)	C9—O2	1.422 (4)
C1—C5	1.371 (4)	C9—C10	1.488 (4)
C1—C2	1.399 (3)	C9—H9A	0.9700
C2—C3	1.370 (3)	C9—H9B	0.9700
C2—H2	0.9300	C10—O3	1.427 (3)
C3—N2	1.381 (3)	C10—H10A	0.9700
C3—C4	1.398 (3)	C10—H10B	0.9700
C4—N1	1.322 (3)	C11—N3	1.452 (3)
C4—N3	1.375 (3)	C11—C12	1.524 (4)
C5—N1	1.347 (3)	C11—H11A	0.9700
C5—H5	0.9300	C11—H11B	0.9700
C6—O1	1.212 (3)	C12—O4	1.389 (3)
C6—N3	1.385 (3)	C12—O5	1.403 (3)
C6—N2	1.387 (3)	C12—H12	0.9800
C7—N2	1.450 (3)	C13—O4	1.403 (4)
C7—C8	1.494 (4)	C13—C14	1.469 (4)
C7—H7A	0.9700	C13—H13A	0.9700
C7—H7B	0.9700	C13—H13B	0.9700
C8—O3	1.389 (3)	C14—O5	1.428 (3)
C8—O2	1.409 (3)	C14—H14A	0.9700
C8—H8	0.9800	C14—H14B	0.9700
C5—C1—C2	121.9 (2)	O3—C10—H10B	111.0
C5—C1—Br1	119.34 (18)	C9—C10—H10B	111.0
C2—C1—Br1	118.71 (19)	H10A—C10—H10B	109.0
C3—C2—C1	114.8 (2)	N3—C11—C12	110.9 (2)
C3—C2—H2	122.6	N3—C11—H11A	109.5
C1—C2—H2	122.6	C12—C11—H11A	109.5
C2—C3—N2	133.6 (2)	N3—C11—H11B	109.5
C2—C3—C4	119.4 (2)	C12—C11—H11B	109.5
N2—C3—C4	107.0 (2)	H11A—C11—H11B	108.0
N1—C4—N3	126.2 (2)	O4—C12—O5	107.53 (19)
N1—C4—C3	126.3 (2)	O4—C12—C11	111.1 (2)
N3—C4—C3	107.5 (2)	O5—C12—C11	110.3 (2)
N1—C5—C1	123.5 (2)	O4—C12—H12	109.3
N1—C5—H5	118.2	O5—C12—H12	109.3
C1—C5—H5	118.2	C11—C12—H12	109.3
O1—C6—N3	127.1 (2)	O4—C13—C14	107.2 (2)
O1—C6—N2	126.8 (2)	O4—C13—H13A	110.3
N3—C6—N2	106.1 (2)	C14—C13—H13A	110.3
N2—C7—C8	114.0 (2)	O4—C13—H13B	110.3
N2—C7—H7A	108.7	C14—C13—H13B	110.3
C8—C7—H7A	108.7	H13A—C13—H13B	108.5
N2—C7—H7B	108.7	O5—C14—C13	104.1 (2)
C8—C7—H7B	108.7	O5—C14—H14A	110.9
H7A—C7—H7B	107.6	C13—C14—H14A	110.9
O3—C8—O2	105.6 (2)	O5—C14—H14B	110.9
O3—C8—C7	112.7 (2)	C13—C14—H14B	110.9
O2—C8—C7	111.7 (2)	H14A—C14—H14B	109.0
O3—C8—H8	108.9	C4—N1—C5	114.0 (2)
O2—C8—H8	108.9	C3—N2—C6	109.6 (2)
C7—C8—H8	108.9	C3—N2—C7	126.3 (2)
O2—C9—C10	105.2 (2)	C6—N2—C7	123.4 (2)
O2—C9—H9A	110.7	C4—N3—C6	109.7 (2)
C10—C9—H9A	110.7	C4—N3—C11	125.6 (2)
O2—C9—H9B	110.7	C6—N3—C11	124.4 (2)
C10—C9—H9B	110.7	C8—O2—C9	106.0 (2)
H9A—C9—H9B	108.8	C8—O3—C10	103.7 (2)
O3—C10—C9	103.8 (2)	C12—O4—C13	107.9 (2)
O3—C10—H10A	111.0	C12—O5—C14	106.51 (19)
C9—C10—H10A	111.0
C5—C1—C2—C3	−1.3 (3)	N3—C6—N2—C7	−171.4 (2)
Br1—C1—C2—C3	178.13 (17)	C8—C7—N2—C3	87.4 (3)
C1—C2—C3—N2	−179.0 (2)	C8—C7—N2—C6	−103.0 (3)
C1—C2—C3—C4	0.3 (3)	N1—C4—N3—C6	179.4 (2)
C2—C3—C4—N1	1.0 (4)	C3—C4—N3—C6	−0.4 (3)
N2—C3—C4—N1	−179.6 (2)	N1—C4—N3—C11	5.4 (4)
C2—C3—C4—N3	−179.2 (2)	C3—C4—N3—C11	−174.4 (2)
N2—C3—C4—N3	0.2 (3)	O1—C6—N3—C4	179.9 (2)
C2—C1—C5—N1	1.3 (4)	N2—C6—N3—C4	0.4 (3)
Br1—C1—C5—N1	−178.18 (18)	O1—C6—N3—C11	−6.0 (4)
N2—C7—C8—O3	64.1 (3)	N2—C6—N3—C11	174.6 (2)
N2—C7—C8—O2	−54.6 (3)	C12—C11—N3—C4	68.0 (3)
O2—C9—C10—O3	−14.6 (3)	C12—C11—N3—C6	−105.2 (3)
N3—C11—C12—O4	60.3 (3)	O3—C8—O2—C9	31.3 (3)
N3—C11—C12—O5	179.4 (2)	C7—C8—O2—C9	154.1 (2)
O4—C13—C14—O5	12.2 (4)	C10—C9—O2—C8	−9.6 (3)
N3—C4—N1—C5	179.2 (2)	O2—C8—O3—C10	−40.7 (3)
C3—C4—N1—C5	−1.1 (3)	C7—C8—O3—C10	−162.9 (2)
C1—C5—N1—C4	0.0 (3)	C9—C10—O3—C8	33.5 (3)
C2—C3—N2—C6	179.4 (3)	O5—C12—O4—C13	−18.7 (3)
C4—C3—N2—C6	0.1 (3)	C11—C12—O4—C13	102.1 (3)
C2—C3—N2—C7	−9.8 (4)	C14—C13—O4—C12	3.6 (4)
C4—C3—N2—C7	170.9 (2)	O4—C12—O5—C14	26.6 (3)
O1—C6—N2—C3	−179.8 (2)	C11—C12—O5—C14	−94.7 (2)
N3—C6—N2—C3	−0.3 (3)	C13—C14—O5—C12	−23.4 (3)
O1—C6—N2—C7	9.1 (4)

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10B···O2i	0.97	2.36	3.291 (4)	160

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C10—H10B⋯O2i	0.97	2.36	3.291 (4)	160

Symmetry code: (i) .