N-[6-(Dibromo-meth-yl)-2-pyrid-yl]-2,2-dimethyl-propionamide.

In the mol-ecular structure of the title compound, C(11)H(14)Br(2)N(2)O, the dimethyl-propionamide substituent is twisted slightly with respect to the pyridine ring, the inter-planar angle being 12.3 (2)°. The dibromo-methyl group is orientated in such a way that the two Br atoms are tilted away from the pyridine ring. In the crystal structure, mol-ecules are associated into supra-molecular chains by weak C-H⋯O inter-actions. The crystal is further stabilized by weak N-H⋯Br and C-H⋯N inter-actions.

Related literature

For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For mol­ecular recognition and N-bromo­succinimides, see, for example: Goswami & Mukherjee, (1997 ▶); Goswami et al. (2000 ▶, 2001 ▶, 2004 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C11H14Br2N2O

M = 350.06

Monoclinic,

a = 13.2936 (7) Å

b = 8.4660 (3) Å

c = 11.9638 (6) Å

β = 99.195 (3)°

V = 1329.15 (11) Å3

Z = 4

Mo Kα radiation

μ = 6.08 mm−1

T = 100 K

0.33 × 0.29 × 0.24 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.114, T max = 0.233

12087 measured reflections

3863 independent reflections

2954 reflections with I > 2σ(I)

R int = 0.039

Refinement

R[F 2 > 2σ(F 2)] = 0.051

wR(F 2) = 0.153

S = 1.10

3863 reflections

152 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 1.98 e Å−3

Δρmin = −1.13 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809007909/tk2385sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809007909/tk2385Isup2.hkl

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

C11H14Br2N2O	F(000) = 688
Mr = 350.06	Dx = 1.749 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3863 reflections
a = 13.2936 (7) Å	θ = 1.6–30.0°
b = 8.4660 (3) Å	µ = 6.08 mm−1
c = 11.9638 (6) Å	T = 100 K
β = 99.195 (3)°	Block, colorless
V = 1329.15 (11) Å3	0.33 × 0.29 × 0.24 mm
Z = 4

Bruker APEXII CCD area-detector diffractometer	3863 independent reflections
Radiation source: sealed tube	2954 reflections with I > 2σ(I)
graphite	Rint = 0.039
φ and ω scans	θmax = 30.0°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −16→18
Tmin = 0.114, Tmax = 0.233	k = −9→11
12087 measured reflections	l = −16→16

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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.153	H atoms treated by a mixture of independent and constrained refinement
S = 1.10	w = 1/[σ2(Fo2) + (0.0946P)2] where P = (Fo2 + 2Fc2)/3
3863 reflections	(Δ/σ)max < 0.001
152 parameters	Δρmax = 1.98 e Å−3
0 restraints	Δρmin = −1.13 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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	−0.01634 (3)	0.15918 (5)	0.82585 (4)	0.02738 (15)
Br2	0.08741 (3)	0.31287 (5)	1.05799 (4)	0.02696 (15)
O1	0.4376 (2)	0.5484 (4)	0.6250 (3)	0.0403 (9)
N1	0.1855 (2)	0.4274 (4)	0.7746 (3)	0.0188 (6)
N2	0.2728 (3)	0.5490 (4)	0.6511 (3)	0.0233 (7)
C1	0.1747 (3)	0.3175 (4)	0.8522 (4)	0.0205 (8)
C2	0.2499 (3)	0.2067 (5)	0.8910 (4)	0.0250 (9)
H2A	0.2416	0.1345	0.9474	0.030*
C3	0.3376 (3)	0.2089 (5)	0.8420 (4)	0.0269 (9)
H3A	0.3887	0.1351	0.8643	0.032*
C4	0.3500 (3)	0.3196 (4)	0.7602 (4)	0.0230 (8)
H4A	0.4084	0.3216	0.7267	0.028*
C5	0.2719 (3)	0.4275 (5)	0.7302 (3)	0.0191 (7)
C6	0.3540 (3)	0.6069 (5)	0.6056 (4)	0.0237 (8)
C7	0.3295 (3)	0.7544 (5)	0.5291 (4)	0.0278 (9)
C8	0.3325 (5)	0.8986 (6)	0.6075 (5)	0.0463 (13)
H8A	0.3962	0.9001	0.6584	0.070*
H8B	0.2774	0.8923	0.6502	0.070*
H8C	0.3260	0.9933	0.5629	0.070*
C9	0.2253 (4)	0.7427 (6)	0.4534 (5)	0.0441 (14)
H9A	0.2227	0.6484	0.4084	0.066*
H9B	0.2152	0.8332	0.4045	0.066*
H9C	0.1727	0.7391	0.4998	0.066*
C10	0.4117 (4)	0.7706 (7)	0.4552 (5)	0.0452 (14)
H10A	0.4150	0.6753	0.4124	0.068*
H10B	0.4763	0.7887	0.5022	0.068*
H10C	0.3959	0.8579	0.4043	0.068*
C11	0.0748 (3)	0.3265 (4)	0.8950 (3)	0.0212 (8)
H11A	0.0433	0.4283	0.8713	0.025*
H1N2	0.224 (3)	0.609 (6)	0.638 (4)	0.023 (12)*

	U11	U22	U33	U12	U13	U23
Br1	0.0269 (2)	0.0317 (3)	0.0252 (2)	−0.00904 (17)	0.00912 (17)	−0.00740 (16)
Br2	0.0314 (3)	0.0321 (3)	0.0176 (2)	0.00285 (17)	0.00477 (17)	0.00017 (15)
O1	0.0224 (16)	0.0365 (19)	0.064 (3)	0.0035 (14)	0.0128 (16)	0.0234 (17)
N1	0.0202 (16)	0.0166 (15)	0.0189 (15)	−0.0010 (12)	0.0012 (13)	−0.0006 (12)
N2	0.0215 (17)	0.0221 (17)	0.0271 (18)	0.0045 (14)	0.0064 (14)	0.0044 (14)
C1	0.0213 (19)	0.0155 (18)	0.025 (2)	−0.0025 (14)	0.0030 (16)	−0.0011 (14)
C2	0.027 (2)	0.0176 (18)	0.031 (2)	0.0014 (15)	0.0064 (17)	0.0041 (16)
C3	0.026 (2)	0.0172 (19)	0.037 (2)	0.0033 (16)	0.0029 (18)	0.0031 (17)
C4	0.0197 (19)	0.0169 (19)	0.033 (2)	0.0014 (14)	0.0070 (17)	0.0001 (15)
C5	0.0186 (18)	0.0168 (18)	0.0219 (18)	−0.0021 (14)	0.0031 (15)	−0.0005 (14)
C6	0.0211 (19)	0.0207 (19)	0.030 (2)	−0.0017 (15)	0.0057 (16)	0.0011 (16)
C7	0.027 (2)	0.024 (2)	0.034 (2)	0.0004 (17)	0.0103 (18)	0.0048 (17)
C8	0.065 (4)	0.022 (2)	0.053 (3)	0.003 (2)	0.010 (3)	0.000 (2)
C9	0.043 (3)	0.035 (3)	0.051 (3)	−0.003 (2)	−0.004 (2)	0.025 (2)
C10	0.046 (3)	0.043 (3)	0.052 (3)	0.012 (2)	0.023 (3)	0.022 (3)
C11	0.024 (2)	0.0194 (19)	0.0206 (19)	−0.0010 (15)	0.0044 (15)	−0.0021 (14)

Br1—C11	1.959 (4)	C4—H4A	0.9300
Br2—C11	1.934 (4)	C6—C7	1.551 (6)
O1—C6	1.205 (5)	C7—C10	1.518 (6)
N1—C1	1.338 (5)	C7—C9	1.532 (7)
N1—C5	1.341 (5)	C7—C8	1.536 (7)
N2—C6	1.374 (5)	C8—H8A	0.9600
N2—C5	1.400 (5)	C8—H8B	0.9600
N2—H1N2	0.82 (5)	C8—H8C	0.9600
C1—C2	1.395 (6)	C9—H9A	0.9600
C1—C11	1.500 (6)	C9—H9B	0.9600
C2—C3	1.386 (6)	C9—H9C	0.9600
C2—H2A	0.9300	C10—H10A	0.9600
C3—C4	1.384 (6)	C10—H10B	0.9600
C3—H3A	0.9300	C10—H10C	0.9600
C4—C5	1.385 (5)	C11—H11A	0.9800
C1—N1—C5	117.9 (3)	C9—C7—C6	112.4 (4)
C6—N2—C5	128.5 (4)	C8—C7—C6	107.2 (4)
C6—N2—H1N2	110 (3)	C7—C8—H8A	109.5
C5—N2—H1N2	120 (3)	C7—C8—H8B	109.5
N1—C1—C2	123.2 (4)	H8A—C8—H8B	109.5
N1—C1—C11	113.6 (3)	C7—C8—H8C	109.5
C2—C1—C11	123.2 (4)	H8A—C8—H8C	109.5
C3—C2—C1	117.2 (4)	H8B—C8—H8C	109.5
C3—C2—H2A	121.4	C7—C9—H9A	109.5
C1—C2—H2A	121.4	C7—C9—H9B	109.5
C4—C3—C2	120.7 (4)	H9A—C9—H9B	109.5
C4—C3—H3A	119.6	C7—C9—H9C	109.5
C2—C3—H3A	119.6	H9A—C9—H9C	109.5
C3—C4—C5	117.5 (4)	H9B—C9—H9C	109.5
C3—C4—H4A	121.3	C7—C10—H10A	109.5
C5—C4—H4A	121.3	C7—C10—H10B	109.5
N1—C5—C4	123.4 (4)	H10A—C10—H10B	109.5
N1—C5—N2	111.6 (3)	C7—C10—H10C	109.5
C4—C5—N2	124.9 (4)	H10A—C10—H10C	109.5
O1—C6—N2	122.4 (4)	H10B—C10—H10C	109.5
O1—C6—C7	123.0 (4)	C1—C11—Br2	113.7 (3)
N2—C6—C7	114.6 (3)	C1—C11—Br1	110.0 (3)
C10—C7—C9	109.2 (4)	Br2—C11—Br1	109.32 (19)
C10—C7—C8	109.4 (4)	C1—C11—H11A	107.9
C9—C7—C8	110.2 (4)	Br2—C11—H11A	107.9
C10—C7—C6	108.2 (4)	Br1—C11—H11A	107.9
C5—N1—C1—C2	1.9 (6)	C5—N2—C6—O1	5.2 (7)
C5—N1—C1—C11	−179.1 (3)	C5—N2—C6—C7	−174.0 (4)
N1—C1—C2—C3	−2.8 (6)	O1—C6—C7—C10	19.8 (6)
C11—C1—C2—C3	178.3 (4)	N2—C6—C7—C10	−161.0 (4)
C1—C2—C3—C4	1.6 (7)	O1—C6—C7—C9	140.5 (5)
C2—C3—C4—C5	0.3 (7)	N2—C6—C7—C9	−40.3 (6)
C1—N1—C5—C4	0.3 (6)	O1—C6—C7—C8	−98.2 (5)
C1—N1—C5—N2	−179.7 (3)	N2—C6—C7—C8	81.0 (5)
C3—C4—C5—N1	−1.3 (6)	N1—C1—C11—Br2	−133.6 (3)
C3—C4—C5—N2	178.6 (4)	C2—C1—C11—Br2	45.5 (5)
C6—N2—C5—N1	165.5 (4)	N1—C1—C11—Br1	103.5 (3)
C6—N2—C5—C4	−14.4 (7)	C2—C1—C11—Br1	−77.5 (5)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1N2···Br1i	0.82 (5)	2.89 (4)	3.587 (4)	144 (4)
C3—H3A···O1ii	0.93	2.41	3.249 (5)	151
C4—H4A···O1	0.93	2.34	2.886 (5)	117
C9—H9B···N1iii	0.96	2.55	3.506 (6)	179

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H1N2⋯Br1i	0.82 (5)	2.89 (4)	3.587 (4)	144 (4)
C3—H3A⋯O1ii	0.93	2.41	3.249 (5)	151
C4—H4A⋯O1	0.93	2.34	2.886 (5)	117
C9—H9B⋯N1iii	0.96	2.55	3.506 (6)	179

Symmetry codes: (i) ; (ii) ; (iii) .