2-Bromo-N-(2-hy-droxy-5-methyl-phen-yl)-2-methyl-propanamide.

In the title mol-ecule, C(11)H(14)BrNO(2), there is twist between the mean plane of the amide group and the benzene ring [the C-N-C-C torsion angle is -172.1 (2)°]. The amide H atom forms an intra-molecular hydrogen bond with the Br atom. In the crystal, inter-molecular O-H⋯O and weak C-H⋯O hydrogen bonds link mol-ecules into a chain along [100].

Related literature

For functional initiators in polymerization processes, see: Matyjaszewski & Xia (2001 ▶); Kato et al. (1995 ▶). For related structures, see: Moreno-Fuquen et al. (2011a ▶,b ▶). For hydrogen-bond graph-set motifs, see: Etter (1990 ▶).

Experimental

Crystal data

C11H14BrNO2

M = 272.14

Monoclinic,

a = 7.4510 (2) Å

b = 13.8498 (4) Å

c = 12.8646 (4) Å

β = 116.324 (2)°

V = 1189.89 (6) Å3

Z = 4

Mo Kα radiation

μ = 3.44 mm−1

T = 123 K

0.30 × 0.10 × 0.08 mm

Data collection

Oxford Diffraction Xcalibur E diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009 ▶) T min = 0.650, T max = 1.000

5803 measured reflections

2886 independent reflections

2437 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.085

S = 1.05

2886 reflections

147 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.73 e Å−3

Δρmin = −0.46 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 (Farrugia, 1997 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PARST (Nardelli, 1995 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811033150/tk2780sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811033150/tk2780Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811033150/tk2780Isup3.cml

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

C11H14BrNO2	F(000) = 552
Mr = 272.14	Dx = 1.519 Mg m−3
Monoclinic, P21/c	Melting point: 385(1) K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 7.4510 (2) Å	Cell parameters from 3082 reflections
b = 13.8498 (4) Å	θ = 3.1–29.4°
c = 12.8646 (4) Å	µ = 3.44 mm−1
β = 116.324 (2)°	T = 123 K
V = 1189.89 (6) Å3	Tablet, colourless
Z = 4	0.30 × 0.10 × 0.08 mm

Oxford Diffraction Xcalibur E diffractometer	2886 independent reflections
Radiation source: fine-focus sealed tube	2437 reflections with I > 2σ(I)
graphite	Rint = 0.023
ω scans	θmax = 29.4°, θmin = 3.1°
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	h = −8→10
Tmin = 0.650, Tmax = 1.000	k = −16→19
5803 measured reflections	l = −16→17

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: inferred from neighbouring sites
wR(F2) = 0.085	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ2(Fo2) + (0.0441P)2 + 0.2346P] where P = (Fo2 + 2Fc2)/3
2886 reflections	(Δ/σ)max < 0.001
147 parameters	Δρmax = 0.73 e Å−3
1 restraint	Δρmin = −0.46 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	0.10479 (3)	0.358681 (19)	0.14350 (2)	0.02782 (10)
O1	−0.0362 (3)	0.54556 (15)	0.34215 (18)	0.0387 (5)
O2	0.5930 (2)	0.53566 (12)	0.32150 (14)	0.0219 (4)
N1	0.2461 (3)	0.51979 (14)	0.32142 (17)	0.0190 (4)
C1	−0.1738 (4)	0.35819 (19)	0.2380 (3)	0.0317 (6)
H1A	−0.0742	0.3209	0.3025	0.048*
H1B	−0.2525	0.3146	0.1739	0.048*
H1C	−0.2629	0.3916	0.2638	0.048*
C2	−0.0677 (3)	0.43204 (18)	0.1973 (2)	0.0227 (5)
C3	−0.2146 (4)	0.4905 (2)	0.0933 (2)	0.0375 (7)
H3A	−0.2935	0.4466	0.0296	0.056*
H3B	−0.1398	0.5352	0.0680	0.056*
H3C	−0.3043	0.5272	0.1158	0.056*
C4	0.0531 (3)	0.50331 (18)	0.2951 (2)	0.0215 (5)
C5	0.3773 (3)	0.58845 (16)	0.39924 (19)	0.0162 (4)
C6	0.5634 (3)	0.59619 (17)	0.39643 (19)	0.0177 (4)
C7	0.7014 (3)	0.66329 (17)	0.4661 (2)	0.0220 (5)
H7	0.8263	0.6696	0.4635	0.026*
C8	0.6582 (3)	0.72175 (17)	0.5400 (2)	0.0220 (5)
H8	0.7538	0.7681	0.5870	0.026*
C9	0.4764 (3)	0.71337 (16)	0.54611 (19)	0.0193 (5)
C10	0.3369 (3)	0.64603 (15)	0.4745 (2)	0.0182 (5)
H10	0.2123	0.6396	0.4774	0.022*
C11	0.4344 (4)	0.77409 (18)	0.6301 (2)	0.0261 (5)
H11A	0.4697	0.7376	0.7019	0.039*
H11B	0.2918	0.7907	0.5955	0.039*
H11C	0.5144	0.8334	0.6476	0.039*
H1H	0.711 (2)	0.540 (2)	0.328 (3)	0.038 (8)*
H1N	0.297 (4)	0.4836 (19)	0.286 (2)	0.027 (7)*

	U11	U22	U33	U12	U13	U23
Br1	0.02120 (15)	0.03380 (17)	0.02828 (15)	0.00141 (11)	0.01082 (11)	−0.01028 (10)
O1	0.0186 (9)	0.0505 (13)	0.0535 (12)	−0.0127 (9)	0.0219 (9)	−0.0306 (10)
O2	0.0130 (8)	0.0300 (9)	0.0261 (9)	−0.0022 (7)	0.0118 (7)	−0.0037 (7)
N1	0.0128 (9)	0.0224 (10)	0.0239 (10)	−0.0013 (8)	0.0100 (8)	−0.0044 (8)
C1	0.0248 (13)	0.0322 (15)	0.0411 (16)	−0.0082 (11)	0.0174 (12)	−0.0120 (12)
C2	0.0149 (11)	0.0267 (13)	0.0256 (12)	0.0011 (10)	0.0082 (9)	−0.0070 (10)
C3	0.0273 (14)	0.0417 (17)	0.0313 (15)	0.0126 (13)	0.0021 (11)	−0.0042 (13)
C4	0.0133 (11)	0.0265 (12)	0.0261 (12)	−0.0020 (10)	0.0101 (9)	−0.0042 (10)
C5	0.0106 (10)	0.0176 (11)	0.0183 (10)	−0.0001 (9)	0.0044 (8)	0.0030 (8)
C6	0.0138 (11)	0.0207 (12)	0.0183 (11)	0.0002 (9)	0.0069 (9)	0.0034 (9)
C7	0.0143 (11)	0.0264 (13)	0.0250 (12)	−0.0049 (10)	0.0084 (9)	0.0024 (10)
C8	0.0174 (11)	0.0216 (12)	0.0230 (12)	−0.0054 (10)	0.0053 (9)	−0.0013 (9)
C9	0.0202 (11)	0.0177 (11)	0.0169 (11)	−0.0003 (10)	0.0056 (9)	0.0025 (9)
C10	0.0139 (11)	0.0206 (12)	0.0207 (11)	0.0004 (9)	0.0081 (9)	0.0024 (9)
C11	0.0277 (13)	0.0257 (13)	0.0241 (12)	−0.0011 (11)	0.0110 (10)	−0.0044 (10)

Br1—C2	1.988 (2)	C3—H3C	0.9800
O1—C4	1.229 (3)	C5—C10	1.387 (3)
O2—C6	1.367 (3)	C5—C6	1.407 (3)
O2—H1H	0.847 (10)	C6—C7	1.381 (3)
N1—C4	1.343 (3)	C7—C8	1.391 (3)
N1—C5	1.412 (3)	C7—H7	0.9500
N1—H1N	0.87 (3)	C8—C9	1.396 (3)
C1—C2	1.520 (3)	C8—H8	0.9500
C1—H1A	0.9800	C9—C10	1.396 (3)
C1—H1B	0.9800	C9—C11	1.508 (3)
C1—H1C	0.9800	C10—H10	0.9500
C2—C3	1.531 (4)	C11—H11A	0.9800
C2—C4	1.537 (3)	C11—H11B	0.9800
C3—H3A	0.9800	C11—H11C	0.9800
C3—H3B	0.9800
C6—O2—H1H	112 (2)	C10—C5—C6	119.7 (2)
C4—N1—C5	128.39 (19)	C10—C5—N1	125.84 (19)
C4—N1—H1N	115.9 (18)	C6—C5—N1	114.43 (19)
C5—N1—H1N	115.7 (18)	O2—C6—C7	124.29 (19)
C2—C1—H1A	109.5	O2—C6—C5	116.13 (19)
C2—C1—H1B	109.5	C7—C6—C5	119.6 (2)
H1A—C1—H1B	109.5	C6—C7—C8	120.2 (2)
C2—C1—H1C	109.5	C6—C7—H7	119.9
H1A—C1—H1C	109.5	C8—C7—H7	119.9
H1B—C1—H1C	109.5	C7—C8—C9	121.0 (2)
C1—C2—C3	112.2 (2)	C7—C8—H8	119.5
C1—C2—C4	110.8 (2)	C9—C8—H8	119.5
C3—C2—C4	107.9 (2)	C8—C9—C10	118.4 (2)
C1—C2—Br1	106.92 (16)	C8—C9—C11	120.6 (2)
C3—C2—Br1	106.75 (16)	C10—C9—C11	121.0 (2)
C4—C2—Br1	112.25 (14)	C5—C10—C9	121.1 (2)
C2—C3—H3A	109.5	C5—C10—H10	119.5
C2—C3—H3B	109.5	C9—C10—H10	119.5
H3A—C3—H3B	109.5	C9—C11—H11A	109.5
C2—C3—H3C	109.5	C9—C11—H11B	109.5
H3A—C3—H3C	109.5	H11A—C11—H11B	109.5
H3B—C3—H3C	109.5	C9—C11—H11C	109.5
O1—C4—N1	123.2 (2)	H11A—C11—H11C	109.5
O1—C4—C2	117.44 (19)	H11B—C11—H11C	109.5
N1—C4—C2	119.26 (19)
C5—N1—C4—O1	−3.6 (4)	C10—C5—C6—C7	−2.1 (3)
C5—N1—C4—C2	173.2 (2)	N1—C5—C6—C7	177.9 (2)
C1—C2—C4—O1	−53.7 (3)	O2—C6—C7—C8	−179.8 (2)
C3—C2—C4—O1	69.5 (3)	C5—C6—C7—C8	1.1 (3)
Br1—C2—C4—O1	−173.2 (2)	C6—C7—C8—C9	0.5 (4)
C1—C2—C4—N1	129.2 (2)	C7—C8—C9—C10	−1.2 (3)
C3—C2—C4—N1	−107.6 (3)	C7—C8—C9—C11	177.4 (2)
Br1—C2—C4—N1	9.8 (3)	C6—C5—C10—C9	1.4 (3)
C4—N1—C5—C10	7.8 (4)	N1—C5—C10—C9	−178.5 (2)
C4—N1—C5—C6	−172.1 (2)	C8—C9—C10—C5	0.2 (3)
C10—C5—C6—O2	178.8 (2)	C11—C9—C10—C5	−178.4 (2)
N1—C5—C6—O2	−1.3 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H1H···O1i	0.85 (1)	1.81 (1)	2.659 (2)	179 (3)
C1—H1C···O2ii	0.98	2.53	3.445 (3)	156.
N1—H1N···Br1	0.87 (3)	2.47 (3)	3.031 (2)	123 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H1H⋯O1i	0.85 (1)	1.81 (1)	2.659 (2)	179 (3)
C1—H1C⋯O2ii	0.98	2.53	3.445 (3)	156
N1—H1N⋯Br1	0.87 (3)	2.47 (3)	3.031 (2)	123 (2)

Symmetry codes: (i) ; (ii) .