N,N'-(1,4-Phenyl-ene)bis-(2-bromo-2-methyl-propanamide).

The mol-ecular structure of the title compound, C(14)H(18)Br(2)N(2)O(2), has one half-mol-ecule in the asymmetric unit. The mol-ecule has a crystallographic inversion centre in the middle of the benzene ring. The C-C-N-C torsion angle between the benzene ring and the bromo-amide group is 149.2 (7)°. The crystal is stabilized by a strong inter-molecular N-H⋯O bond and weak C-H⋯O inter-actions. These contacts give rise to a three-dimensional network.

Related literature

For the use of the title compound as an initiator in atom transfer radical polymerization and other polymerization studies, see: Ashraf et al. (1994 ▶); Domenicano et al. (1977 ▶); Kuipers et al. (1989 ▶); Matyjaszewski & Xia (2001 ▶); Miroshnikova et al. (2007 ▶); Rollison et al. (2006 ▶). For similar structures, see: Haridharan et al. (2010 ▶).

Experimental

Crystal data

C14H18Br2N2O2

M = 406.12

Monoclinic,

a = 13.834 (3) Å

b = 6.4746 (13) Å

c = 9.4642 (18) Å

β = 103.807 (9)°

V = 823.2 (3) Å3

Z = 2

Mo Kα radiation

μ = 4.93 mm−1

T = 298 K

0.35 × 0.22 × 0.05 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T min = 0.278, T max = 0.791

1834 measured reflections

1834 independent reflections

664 reflections with I > 2σ(I)

R int = 0.000

Refinement

R[F 2 > 2σ(F 2)] = 0.056

wR(F 2) = 0.146

S = 0.94

1834 reflections

93 parameters

H-atom parameters constrained

Δρmax = 0.54 e Å−3

Δρmin = −0.56 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: APEX2 and SAINT-Plus (Bruker, 2004 ▶); data reduction: SAINT-Plus and XPREP (Bruker, 2004 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812003479/bv2195sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812003479/bv2195Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812003479/bv2195Isup3.cml

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

C14H18Br2N2O2	F(000) = 404
Mr = 406.12	Dx = 1.638 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1219 reflections
a = 13.834 (3) Å	θ = 0.0–0.0°
b = 6.4746 (13) Å	µ = 4.93 mm−1
c = 9.4642 (18) Å	T = 298 K
β = 103.807 (9)°	Block, colourless
V = 823.2 (3) Å3	0.35 × 0.22 × 0.05 mm
Z = 2

Bruker APEXII CCD area-detector diffractometer	1834 independent reflections
Radiation source: fine-focus sealed tube	664 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.000
φ and ω scans	θmax = 27.8°, θmin = 3.0°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −18→17
Tmin = 0.278, Tmax = 0.791	k = 0→8
1834 measured reflections	l = 0→11

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)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.146	H-atom parameters constrained
S = 0.94	w = 1/[σ2(Fo2) + (0.0575P)2] where P = (Fo2 + 2Fc2)/3
1834 reflections	(Δ/σ)max < 0.001
93 parameters	Δρmax = 0.54 e Å−3
0 restraints	Δρmin = −0.56 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	0.90343 (6)	0.80012 (14)	0.54184 (10)	0.0699 (4)
O1	0.7011 (3)	0.5876 (8)	0.6804 (5)	0.0520 (14)
N1	0.6647 (4)	0.7640 (8)	0.4699 (6)	0.0436 (16)
H1A	0.6809	0.7779	0.3882	0.052*
C1	0.5804 (5)	0.8774 (11)	0.4872 (7)	0.0364 (18)
C2	0.5188 (5)	0.8134 (11)	0.5735 (8)	0.050 (2)
H2	0.5308	0.6887	0.6234	0.060*
C3	0.5607 (5)	1.0646 (13)	0.4144 (7)	0.045 (2)
H3	0.6021	1.1089	0.3561	0.054*
C4	0.7212 (5)	0.6389 (10)	0.5664 (8)	0.0366 (18)
C5	0.8137 (4)	0.5549 (10)	0.5272 (7)	0.0387 (18)
C6	0.8682 (6)	0.4020 (14)	0.6398 (9)	0.079 (3)
H6A	0.8881	0.4692	0.7327	0.118*
H6B	0.9261	0.3518	0.6116	0.118*
H6C	0.8250	0.2884	0.6465	0.118*
C7	0.7975 (5)	0.4668 (11)	0.3732 (7)	0.051 (2)
H7A	0.8601	0.4226	0.3567	0.076*
H7B	0.7693	0.5714	0.3036	0.076*
H7C	0.7529	0.3512	0.3627	0.076*

	U11	U22	U33	U12	U13	U23
Br1	0.0573 (6)	0.0714 (7)	0.0882 (8)	−0.0096 (5)	0.0316 (4)	−0.0175 (5)
O1	0.056 (3)	0.074 (4)	0.035 (3)	0.008 (3)	0.028 (3)	0.009 (3)
N1	0.053 (4)	0.056 (4)	0.032 (4)	0.018 (3)	0.028 (3)	0.011 (3)
C1	0.040 (4)	0.046 (5)	0.028 (4)	0.003 (3)	0.018 (3)	0.000 (4)
C2	0.056 (5)	0.050 (5)	0.052 (5)	0.013 (4)	0.027 (4)	0.018 (4)
C3	0.043 (4)	0.066 (6)	0.033 (5)	0.010 (4)	0.026 (3)	0.009 (4)
C4	0.045 (4)	0.032 (5)	0.038 (5)	0.007 (3)	0.021 (4)	0.004 (4)
C5	0.037 (4)	0.044 (5)	0.041 (5)	0.012 (4)	0.022 (3)	0.012 (4)
C6	0.095 (7)	0.092 (7)	0.062 (6)	0.042 (6)	0.044 (5)	0.028 (5)
C7	0.076 (5)	0.041 (5)	0.046 (5)	0.013 (4)	0.036 (4)	−0.006 (4)

Br1—C5	2.000 (7)	C3—H3	0.9300
O1—C4	1.223 (7)	C4—C5	1.516 (8)
N1—C4	1.326 (8)	C5—C6	1.517 (9)
N1—C1	1.421 (8)	C5—C7	1.531 (9)
N1—H1A	0.8600	C6—H6A	0.9600
C1—C2	1.377 (8)	C6—H6B	0.9600
C1—C3	1.389 (9)	C6—H6C	0.9600
C2—C3i	1.381 (9)	C7—H7A	0.9600
C2—H2	0.9300	C7—H7B	0.9600
C3—C2i	1.381 (9)	C7—H7C	0.9600
C4—N1—C1	127.0 (5)	C6—C5—C7	111.2 (6)
C4—N1—H1A	116.5	C4—C5—Br1	104.2 (4)
C1—N1—H1A	116.5	C6—C5—Br1	105.8 (5)
C2—C1—C3	118.8 (6)	C7—C5—Br1	108.0 (4)
C2—C1—N1	123.6 (7)	C5—C6—H6A	109.5
C3—C1—N1	117.6 (5)	C5—C6—H6B	109.5
C1—C2—C3i	119.7 (7)	H6A—C6—H6B	109.5
C1—C2—H2	120.2	C5—C6—H6C	109.5
C3i—C2—H2	120.2	H6A—C6—H6C	109.5
C2i—C3—C1	121.6 (6)	H6B—C6—H6C	109.5
C2i—C3—H3	119.2	C5—C7—H7A	109.5
C1—C3—H3	119.2	C5—C7—H7B	109.5
O1—C4—N1	123.5 (6)	H7A—C7—H7B	109.5
O1—C4—C5	120.1 (6)	C5—C7—H7C	109.5
N1—C4—C5	116.4 (6)	H7A—C7—H7C	109.5
C4—C5—C6	111.7 (5)	H7B—C7—H7C	109.5
C4—C5—C7	115.2 (6)
C4—N1—C1—C2	−29.5 (11)	C1—N1—C4—C5	−173.4 (6)
C4—N1—C1—C3	149.4 (7)	O1—C4—C5—C6	2.8 (10)
C3—C1—C2—C3i	0.1 (12)	N1—C4—C5—C6	−175.8 (7)
N1—C1—C2—C3i	179.0 (6)	O1—C4—C5—C7	130.9 (7)
C2—C1—C3—C2i	−0.2 (12)	N1—C4—C5—C7	−47.8 (8)
N1—C1—C3—C2i	−179.1 (6)	O1—C4—C5—Br1	−111.0 (6)
C1—N1—C4—O1	8.0 (11)	N1—C4—C5—Br1	70.4 (7)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1ii	0.86	2.23	3.057 (7)	162
C7—H7B···O1ii	0.96	2.57	3.503 (9)	164

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O1i	0.86	2.23	3.057 (7)	162
C7—H7B⋯O1i	0.96	2.57	3.503 (9)	164

Symmetry code: (i) .