2-Bromo-2-methyl-N-(4-nitro-phen-yl)propanamide.

The title compound, C(10)H(11)BrN(2)O(3), exhibits a small twist between the amide residue and benzene ring [the C-N-C-C torsion angle = 12.7 (4)°]. The crystal structure is stabilized by weak N-H⋯O, C-H⋯Br and C-H⋯O inter-actions. These lead to supra-molecular layers in the bc plane.

Related literature

For initiators in ATRP (polymerization by atom transfer radical) processes, see: Matyjaszewski & Xia (2001 ▶); Pietrasik & Tsarevsky (2010 ▶). For graph-set notation of hydrogen-bond patterns, see: Etter (1990 ▶).

Experimental

Crystal data

C10H11BrN2O3

M = 287.11

Monoclinic,

a = 24.1245 (12) Å

b = 5.8507 (3) Å

c = 15.4723 (8) Å

β = 91.837 (5)°

V = 2182.72 (19) Å3

Z = 8

Mo Kα radiation

μ = 3.76 mm−1

T = 123 K

0.60 × 0.05 × 0.05 mm

Data collection

Oxford Diffraction Xcalibur E diffractometer

Absorption correction: analytical (CrysAlis PRO; Oxford Diffraction, 2009 ▶) T min = 0.444, T max = 1.000

5100 measured reflections

2633 independent reflections

2197 reflections with I > 2σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.032

wR(F 2) = 0.068

S = 1.06

2633 reflections

151 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.55 e Å−3

Δρmin = −0.60 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis CCD; data reduction: CrysAlis CCD; 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 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811005320/tk2720sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811005320/tk2720Isup2.hkl

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

C10H11BrN2O3	F(000) = 1152
Mr = 287.11	Dx = 1.747 Mg m−3
Monoclinic, C2/c	Melting point: 385(1) K
Hall symbol: -C 2yc	Mo Kα radiation, λ = 0.71073 Å
a = 24.1245 (12) Å	Cell parameters from 2722 reflections
b = 5.8507 (3) Å	θ = 3.2–29.3°
c = 15.4723 (8) Å	µ = 3.76 mm−1
β = 91.837 (5)°	T = 123 K
V = 2182.72 (19) Å3	Fragment cut from needle, colourless
Z = 8	0.60 × 0.05 × 0.05 mm

Oxford Diffraction Xcalibur E diffractometer	2633 independent reflections
Radiation source: fine-focus sealed tube	2197 reflections with I > 2σ(I)
graphite	Rint = 0.032
ω scans	θmax = 29.0°, θmin = 3.2°
Absorption correction: analytical (CrysAlis PRO; Oxford Diffraction, 2009)	h = −32→18
Tmin = 0.444, Tmax = 1.000	k = −6→7
5100 measured reflections	l = −19→21

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)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.068	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ2(Fo2) + (0.0213P)2] where P = (Fo2 + 2Fc2)/3
2633 reflections	(Δ/σ)max < 0.001
151 parameters	Δρmax = 0.55 e Å−3
0 restraints	Δρmin = −0.60 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	0.418223 (9)	−0.36757 (5)	0.230618 (14)	0.01800 (9)
O1	0.33754 (6)	−0.2340 (4)	0.04409 (11)	0.0205 (4)
O2	0.09326 (6)	0.3711 (4)	0.06453 (11)	0.0219 (4)
O3	0.12126 (7)	0.6341 (3)	0.15486 (11)	0.0224 (4)
N1	0.34163 (8)	0.0629 (4)	0.13870 (13)	0.0177 (5)
N2	0.12933 (8)	0.4612 (4)	0.11152 (12)	0.0175 (5)
C1	0.44903 (10)	−0.3344 (5)	0.05532 (15)	0.0205 (6)
H1A	0.4520	−0.2507	0.0008	0.031*
H1B	0.4251	−0.4681	0.0461	0.031*
H1C	0.4860	−0.3844	0.0756	0.031*
C2	0.42421 (9)	−0.1793 (5)	0.12266 (14)	0.0156 (5)
C3	0.46064 (9)	0.0238 (5)	0.14342 (16)	0.0209 (6)
H3A	0.4986	−0.0283	0.1564	0.031*
H3B	0.4465	0.1044	0.1937	0.031*
H3C	0.4605	0.1275	0.0937	0.031*
C4	0.36323 (9)	−0.1220 (5)	0.09765 (14)	0.0143 (5)
C5	0.28757 (9)	0.1555 (5)	0.12844 (14)	0.0133 (5)
C6	0.24391 (9)	0.0415 (5)	0.08499 (14)	0.0156 (5)
H6	0.2497	−0.1040	0.0595	0.019*
C7	0.19187 (9)	0.1446 (5)	0.07971 (14)	0.0154 (5)
H7	0.1618	0.0700	0.0503	0.018*
C8	0.18422 (9)	0.3543 (5)	0.11722 (14)	0.0135 (5)
C9	0.22692 (9)	0.4702 (5)	0.16051 (14)	0.0158 (5)
H9	0.2208	0.6157	0.1857	0.019*
C10	0.27856 (9)	0.3680 (5)	0.16594 (14)	0.0150 (5)
H10	0.3083	0.4438	0.1957	0.018*
H1N	0.3624 (11)	0.132 (5)	0.1742 (17)	0.028 (8)*

	U11	U22	U33	U12	U13	U23
Br1	0.01677 (13)	0.01963 (16)	0.01755 (13)	0.00024 (10)	−0.00059 (9)	0.00090 (10)
O1	0.0181 (8)	0.0222 (12)	0.0211 (9)	0.0011 (8)	−0.0017 (7)	−0.0079 (8)
O2	0.0143 (8)	0.0292 (13)	0.0218 (9)	0.0013 (8)	−0.0029 (7)	0.0000 (8)
O3	0.0204 (9)	0.0223 (12)	0.0247 (9)	0.0072 (8)	0.0027 (7)	−0.0027 (9)
N1	0.0135 (10)	0.0205 (14)	0.0187 (11)	0.0023 (9)	−0.0038 (8)	−0.0075 (10)
N2	0.0183 (10)	0.0190 (14)	0.0152 (10)	0.0039 (9)	0.0026 (8)	0.0028 (9)
C1	0.0180 (12)	0.0222 (17)	0.0214 (12)	0.0066 (11)	0.0030 (10)	−0.0025 (11)
C2	0.0151 (11)	0.0158 (15)	0.0159 (11)	0.0025 (10)	0.0004 (9)	−0.0007 (10)
C3	0.0141 (11)	0.0220 (17)	0.0265 (13)	0.0001 (11)	0.0008 (10)	0.0007 (12)
C4	0.0166 (11)	0.0144 (14)	0.0122 (11)	−0.0001 (10)	0.0032 (9)	0.0011 (10)
C5	0.0127 (11)	0.0165 (15)	0.0109 (10)	−0.0002 (10)	0.0020 (8)	0.0010 (10)
C6	0.0176 (11)	0.0145 (15)	0.0148 (11)	0.0015 (10)	0.0005 (9)	−0.0023 (10)
C7	0.0121 (11)	0.0187 (16)	0.0152 (11)	−0.0004 (10)	−0.0013 (9)	0.0010 (10)
C8	0.0119 (11)	0.0170 (15)	0.0117 (11)	0.0030 (10)	0.0024 (8)	0.0034 (10)
C9	0.0200 (12)	0.0120 (14)	0.0155 (11)	0.0010 (10)	0.0030 (9)	−0.0018 (10)
C10	0.0143 (11)	0.0177 (15)	0.0130 (11)	−0.0018 (10)	−0.0001 (8)	−0.0016 (10)

Br1—C2	2.010 (2)	C3—H3A	0.9800
O1—C4	1.211 (3)	C3—H3B	0.9800
O2—N2	1.234 (3)	C3—H3C	0.9800
O3—N2	1.232 (3)	C5—C10	1.392 (4)
N1—C4	1.366 (3)	C5—C6	1.400 (3)
N1—C5	1.416 (3)	C6—C7	1.393 (3)
N1—H1N	0.84 (3)	C6—H6	0.9500
N2—C8	1.465 (3)	C7—C8	1.373 (4)
C1—C2	1.519 (3)	C7—H7	0.9500
C1—H1A	0.9800	C8—C9	1.387 (3)
C1—H1B	0.9800	C9—C10	1.382 (3)
C1—H1C	0.9800	C9—H9	0.9500
C2—C3	1.506 (4)	C10—H10	0.9500
C2—C4	1.546 (3)
C4—N1—C5	127.9 (2)	H3B—C3—H3C	109.5
C4—N1—H1N	117 (2)	O1—C4—N1	123.5 (2)
C5—N1—H1N	115 (2)	O1—C4—C2	121.0 (2)
O3—N2—O2	123.4 (2)	N1—C4—C2	115.4 (2)
O3—N2—C8	118.4 (2)	C10—C5—C6	120.1 (2)
O2—N2—C8	118.2 (2)	C10—C5—N1	116.8 (2)
C2—C1—H1A	109.5	C6—C5—N1	123.2 (2)
C2—C1—H1B	109.5	C7—C6—C5	119.0 (2)
H1A—C1—H1B	109.5	C7—C6—H6	120.5
C2—C1—H1C	109.5	C5—C6—H6	120.5
H1A—C1—H1C	109.5	C8—C7—C6	119.7 (2)
H1B—C1—H1C	109.5	C8—C7—H7	120.1
C3—C2—C1	112.2 (2)	C6—C7—H7	120.1
C3—C2—C4	115.2 (2)	C7—C8—C9	122.2 (2)
C1—C2—C4	110.53 (19)	C7—C8—N2	119.3 (2)
C3—C2—Br1	108.18 (15)	C9—C8—N2	118.5 (2)
C1—C2—Br1	106.45 (18)	C10—C9—C8	118.2 (2)
C4—C2—Br1	103.51 (14)	C10—C9—H9	120.9
C2—C3—H3A	109.5	C8—C9—H9	120.9
C2—C3—H3B	109.5	C9—C10—C5	120.9 (2)
H3A—C3—H3B	109.5	C9—C10—H10	119.6
C2—C3—H3C	109.5	C5—C10—H10	119.6
H3A—C3—H3C	109.5
C5—N1—C4—O1	0.7 (4)	C5—C6—C7—C8	−0.3 (3)
C5—N1—C4—C2	179.5 (2)	C6—C7—C8—C9	0.3 (4)
C3—C2—C4—O1	145.0 (2)	C6—C7—C8—N2	−179.9 (2)
C1—C2—C4—O1	16.6 (3)	O3—N2—C8—C7	170.6 (2)
Br1—C2—C4—O1	−97.1 (2)	O2—N2—C8—C7	−8.3 (3)
C3—C2—C4—N1	−33.9 (3)	O3—N2—C8—C9	−9.6 (3)
C1—C2—C4—N1	−162.3 (2)	O2—N2—C8—C9	171.6 (2)
Br1—C2—C4—N1	84.0 (2)	C7—C8—C9—C10	−0.4 (3)
C4—N1—C5—C10	−168.9 (2)	N2—C8—C9—C10	179.8 (2)
C4—N1—C5—C6	12.7 (4)	C8—C9—C10—C5	0.5 (3)
C10—C5—C6—C7	0.4 (3)	C6—C5—C10—C9	−0.5 (3)
N1—C5—C6—C7	178.7 (2)	N1—C5—C10—C9	−179.0 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O1	0.95	2.27	2.862 (3)	120
C7—H7···O1i	0.95	2.45	3.139 (3)	129
N1—H1n···O3ii	0.84 (3)	2.66 (3)	3.316 (3)	136 (2)
C10—H10···Br1iii	0.95	2.91	3.812 (2)	160

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯O1	0.95	2.27	2.862 (3)	120
C7—H7⋯O1i	0.95	2.45	3.139 (3)	129
N1—H1n⋯O3ii	0.84 (3)	2.66 (3)	3.316 (3)	136 (2)
C10—H10⋯Br1iii	0.95	2.91	3.812 (2)	160

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