tert-Butyl N-(5-bromo-1H-imidazo[4,5-b]pyridin-2-ylmeth-yl)carbamate.

In the mol-ecule of the title compound, C(12)H(15)BrN(4)O(2), the imidazole and pyridine rings are strictly coplanar [maximum deviation 0.006 (3) Å]. In the crystal structure, mol-ecules are linked into chains running parallel to the a axis by inter-molecular N-H⋯O hydrogen bonds. Centrosymmetrically related chains are further connected by N-H⋯N hydrogen-bonding inter-actions to form a two-dimensional layer structure parallel to the ab plane.

Related literature

For general background on the properties of imidazole deriv­atives, see: Dai et al. (2004 ▶); Durant et al. (1973 ▶); Wang et al. (2007 ▶). For the crystal structures of related compounds, see: Lorenc et al. (2008 ▶).

Experimental

Crystal data

C12H15BrN4O2

M = 327.19

Orthorhombic,

a = 10.7400 (11) Å

b = 9.6717 (9) Å

c = 28.215 (3) Å

V = 2930.8 (5) Å3

Z = 8

Mo Kα radiation

μ = 2.81 mm−1

T = 298 (2) K

0.20 × 0.10 × 0.05 mm

Data collection

Bruker SMART APEX area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2002 ▶) T min = 0.604, T max = 0.872

16102 measured reflections

3374 independent reflections

2285 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.102

S = 1.01

3374 reflections

180 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.72 e Å−3

Δρmin = −0.65 e Å−3

Data collection: SMART (Bruker, 2002 ▶); cell refinement: SAINT (Bruker, 2002 ▶); data reduction: SAINT; 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 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808035393/rz2259sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808035393/rz2259Isup2.hkl

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

C12H15BrN4O2	F000 = 1328
Mr = 327.19	Dx = 1.483 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 4297 reflections
a = 10.7400 (11) Å	θ = 2.4–24.9º
b = 9.6717 (9) Å	µ = 2.81 mm−1
c = 28.215 (3) Å	T = 298 (2) K
V = 2930.8 (5) Å3	Plate, colourless
Z = 8	0.20 × 0.10 × 0.05 mm

Bruker SMART APEX area-detector diffractometer	3374 independent reflections
Radiation source: fine-focus sealed tube	2285 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.031
T = 298(2) K	θmax = 27.6º
φ and ω scans	θmin = 2.4º
Absorption correction: multi-scan(SADABS; Bruker, 2002)	h = −13→13
Tmin = 0.604, Tmax = 0.872	k = −12→8
16102 measured reflections	l = −36→29

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.038	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.102	w = 1/[σ2(Fo2) + (0.0412P)2 + 2.0629P] where P = (Fo2 + 2Fc2)/3
S = 1.01	(Δ/σ)max = 0.001
3374 reflections	Δρmax = 0.72 e Å−3
180 parameters	Δρmin = −0.65 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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
Br1	0.13230 (4)	0.06577 (4)	0.356022 (12)	0.07448 (16)
O1	0.2545 (2)	0.37496 (19)	0.61523 (7)	0.0588 (5)
O2	0.1723 (2)	0.55519 (18)	0.65633 (7)	0.0532 (5)
N1	0.0365 (2)	0.3710 (2)	0.45039 (8)	0.0492 (5)
N2	0.1726 (2)	0.4846 (2)	0.50653 (8)	0.0425 (5)
N3	0.35221 (19)	0.3775 (2)	0.48963 (8)	0.0481 (5)
N4	0.2808 (2)	0.5942 (2)	0.59153 (8)	0.0441 (5)
C1	0.0386 (3)	0.2736 (3)	0.41650 (10)	0.0508 (7)
H1	−0.0350	0.2529	0.4006	0.061*
C2	0.1457 (3)	0.2029 (3)	0.40420 (9)	0.0488 (6)
C3	0.2584 (3)	0.2271 (3)	0.42539 (9)	0.0499 (6)
H3	0.3301	0.1795	0.4167	0.060*
C4	0.2590 (2)	0.3268 (3)	0.46047 (8)	0.0426 (6)
C5	0.1455 (2)	0.3930 (3)	0.47101 (9)	0.0395 (5)
C6	0.2964 (2)	0.4704 (3)	0.51590 (9)	0.0414 (6)
C7	0.3610 (2)	0.5565 (3)	0.55229 (10)	0.0463 (6)
H7A	0.4320	0.5056	0.5644	0.056*
H7B	0.3920	0.6400	0.5374	0.056*
C8	0.2370 (2)	0.4976 (3)	0.62088 (9)	0.0411 (6)
C9	0.1098 (3)	0.4696 (3)	0.69213 (10)	0.0563 (7)
C10	0.2031 (4)	0.3846 (5)	0.71874 (13)	0.0989 (13)
H10A	0.2389	0.3172	0.6978	0.148*
H10B	0.1625	0.3384	0.7446	0.148*
H10C	0.2675	0.4436	0.7308	0.148*
C11	0.0119 (4)	0.3815 (5)	0.66859 (16)	0.1005 (14)
H11A	0.0515	0.3131	0.6491	0.151*
H11B	−0.0406	0.4389	0.6493	0.151*
H11C	−0.0375	0.3366	0.6924	0.151*
C12	0.0497 (4)	0.5769 (4)	0.72365 (14)	0.0929 (13)
H12A	0.1132	0.6315	0.7386	0.139*
H12B	0.0005	0.5317	0.7474	0.139*
H12C	−0.0027	0.6358	0.7049	0.139*
H2	0.124 (3)	0.537 (3)	0.5189 (11)	0.051 (9)*
H3A	0.272 (2)	0.678 (3)	0.5990 (8)	0.034 (7)*

	U11	U22	U33	U12	U13	U23
Br1	0.0908 (3)	0.0764 (3)	0.0563 (2)	0.00984 (19)	0.00153 (17)	−0.02719 (16)
O1	0.0800 (14)	0.0302 (10)	0.0660 (12)	0.0025 (9)	0.0186 (11)	−0.0051 (9)
O2	0.0700 (13)	0.0381 (10)	0.0516 (11)	0.0002 (9)	0.0197 (9)	−0.0059 (8)
N1	0.0436 (12)	0.0482 (13)	0.0559 (14)	0.0046 (10)	−0.0002 (10)	−0.0114 (11)
N2	0.0382 (12)	0.0406 (12)	0.0488 (13)	0.0050 (10)	0.0065 (10)	−0.0055 (10)
N3	0.0387 (11)	0.0575 (14)	0.0482 (12)	0.0069 (10)	0.0078 (10)	−0.0079 (11)
N4	0.0540 (14)	0.0259 (11)	0.0524 (13)	−0.0004 (9)	0.0092 (10)	−0.0055 (9)
C1	0.0515 (16)	0.0472 (16)	0.0539 (16)	0.0033 (13)	−0.0026 (13)	−0.0078 (13)
C2	0.0593 (17)	0.0493 (15)	0.0379 (13)	0.0037 (13)	0.0066 (12)	−0.0044 (11)
C3	0.0513 (16)	0.0556 (16)	0.0427 (14)	0.0107 (13)	0.0110 (12)	−0.0047 (12)
C4	0.0414 (13)	0.0478 (15)	0.0385 (12)	0.0051 (11)	0.0104 (11)	0.0005 (11)
C5	0.0417 (13)	0.0368 (13)	0.0401 (13)	0.0018 (11)	0.0069 (11)	−0.0008 (10)
C6	0.0391 (13)	0.0430 (14)	0.0420 (14)	−0.0003 (11)	0.0083 (11)	0.0012 (11)
C7	0.0411 (13)	0.0492 (15)	0.0486 (15)	−0.0048 (12)	0.0061 (12)	−0.0017 (12)
C8	0.0457 (14)	0.0332 (13)	0.0445 (13)	−0.0005 (11)	0.0024 (11)	−0.0051 (11)
C9	0.0630 (18)	0.0561 (17)	0.0499 (16)	−0.0051 (14)	0.0154 (14)	−0.0002 (13)
C10	0.109 (3)	0.124 (3)	0.064 (2)	0.021 (3)	0.009 (2)	0.025 (2)
C11	0.085 (3)	0.115 (3)	0.101 (3)	−0.044 (3)	0.024 (2)	−0.015 (3)
C12	0.109 (3)	0.093 (3)	0.077 (2)	0.001 (2)	0.045 (2)	−0.012 (2)

Br1—C2	1.904 (3)	C3—H3	0.9300
O1—C8	1.211 (3)	C4—C5	1.409 (3)
O2—C8	1.339 (3)	C6—C7	1.493 (4)
O2—C9	1.469 (3)	C7—H7A	0.9700
N1—C5	1.325 (3)	C7—H7B	0.9700
N1—C1	1.342 (3)	C9—C10	1.498 (5)
N2—C6	1.362 (3)	C9—C11	1.507 (5)
N2—C5	1.369 (3)	C9—C12	1.512 (4)
N2—H2	0.81 (3)	C10—H10A	0.9600
N3—C6	1.310 (3)	C10—H10B	0.9600
N3—C4	1.385 (3)	C10—H10C	0.9600
N4—C8	1.335 (3)	C11—H11A	0.9600
N4—C7	1.449 (3)	C11—H11B	0.9600
N4—H3A	0.84 (3)	C11—H11C	0.9600
C1—C2	1.383 (4)	C12—H12A	0.9600
C1—H1	0.9300	C12—H12B	0.9600
C2—C3	1.370 (4)	C12—H12C	0.9600
C3—C4	1.382 (3)
C8—O2—C9	121.1 (2)	N4—C7—H7B	109.0
C5—N1—C1	114.3 (2)	C6—C7—H7B	109.0
C6—N2—C5	106.5 (2)	H7A—C7—H7B	107.8
C6—N2—H2	128 (2)	O1—C8—N4	123.3 (2)
C5—N2—H2	126 (2)	O1—C8—O2	125.9 (2)
C6—N3—C4	104.4 (2)	N4—C8—O2	110.8 (2)
C8—N4—C7	120.4 (2)	O2—C9—C10	110.4 (3)
C8—N4—H3A	118.5 (17)	O2—C9—C11	109.5 (3)
C7—N4—H3A	120.2 (17)	C10—C9—C11	112.1 (3)
N1—C1—C2	122.6 (3)	O2—C9—C12	102.3 (2)
N1—C1—H1	118.7	C10—C9—C12	111.6 (3)
C2—C1—H1	118.7	C11—C9—C12	110.5 (3)
C3—C2—C1	122.8 (2)	C9—C10—H10A	109.5
C3—C2—Br1	119.8 (2)	C9—C10—H10B	109.5
C1—C2—Br1	117.4 (2)	H10A—C10—H10B	109.5
C2—C3—C4	115.9 (2)	C9—C10—H10C	109.5
C2—C3—H3	122.1	H10A—C10—H10C	109.5
C4—C3—H3	122.1	H10B—C10—H10C	109.5
C3—C4—N3	132.5 (2)	C9—C11—H11A	109.5
C3—C4—C5	117.7 (2)	C9—C11—H11B	109.5
N3—C4—C5	109.8 (2)	H11A—C11—H11B	109.5
N1—C5—N2	127.9 (2)	C9—C11—H11C	109.5
N1—C5—C4	126.8 (2)	H11A—C11—H11C	109.5
N2—C5—C4	105.4 (2)	H11B—C11—H11C	109.5
N3—C6—N2	114.0 (2)	C9—C12—H12A	109.5
N3—C6—C7	124.0 (2)	C9—C12—H12B	109.5
N2—C6—C7	122.1 (2)	H12A—C12—H12B	109.5
N4—C7—C6	113.0 (2)	C9—C12—H12C	109.5
N4—C7—H7A	109.0	H12A—C12—H12C	109.5
C6—C7—H7A	109.0	H12B—C12—H12C	109.5
C5—N1—C1—C2	−0.2 (4)	N3—C4—C5—N2	0.5 (3)
N1—C1—C2—C3	−0.4 (4)	C4—N3—C6—N2	0.4 (3)
N1—C1—C2—Br1	179.1 (2)	C4—N3—C6—C7	−178.3 (2)
C1—C2—C3—C4	0.5 (4)	C5—N2—C6—N3	−0.1 (3)
Br1—C2—C3—C4	−178.99 (19)	C5—N2—C6—C7	178.7 (2)
C2—C3—C4—N3	179.1 (3)	C8—N4—C7—C6	65.8 (3)
C2—C3—C4—C5	0.0 (4)	N3—C6—C7—N4	−149.7 (2)
C6—N3—C4—C3	−179.6 (3)	N2—C6—C7—N4	31.7 (3)
C6—N3—C4—C5	−0.5 (3)	C7—N4—C8—O1	−4.5 (4)
C1—N1—C5—N2	−179.8 (3)	C7—N4—C8—O2	175.7 (2)
C1—N1—C5—C4	0.7 (4)	C9—O2—C8—O1	−2.6 (4)
C6—N2—C5—N1	−179.8 (3)	C9—O2—C8—N4	177.2 (2)
C6—N2—C5—C4	−0.3 (3)	C8—O2—C9—C10	61.7 (4)
C3—C4—C5—N1	−0.7 (4)	C8—O2—C9—C11	−62.3 (4)
N3—C4—C5—N1	−179.9 (2)	C8—O2—C9—C12	−179.5 (3)
C3—C4—C5—N2	179.8 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···N1i	0.81 (3)	2.12 (3)	2.911 (3)	165 (3)
N4—H3A···O1ii	0.84 (3)	1.98 (3)	2.822 (3)	178 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯N1i	0.81 (3)	2.12 (3)	2.911 (3)	165 (3)
N4—H3A⋯O1ii	0.84 (3)	1.98 (3)	2.822 (3)	178 (2)

Symmetry codes: (i) ; (ii) .