2-(4-Bromo-phen-yl)-N-(2,6-dimethyl-phen-yl)acetamide.

In the title compound, C(16)H(16)BrNO, the dihedral angle between the benzene rings is 69.8 (2)°. In the crystal, N-H⋯O hydrogen bonds link the mol-ecules into C(4) chains propagating in [100]. Adjacent mol-ecules in the chains are also linked by C-H⋯O inter-actions which, along with the N-H⋯O hydrogen bonds, generate R(2) (1)(6) loops.

Related literature

For general background to the title compound and for related structures, see: Fun et al. (2011a ▶,b ▶, 2012a ▶,b ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C16H16BrNO

M = 318.21

Monoclinic,

a = 4.7146 (6) Å

b = 22.999 (3) Å

c = 13.5350 (15) Å

β = 91.138 (3)°

V = 1467.3 (3) Å3

Z = 4

Mo Kα radiation

μ = 2.79 mm−1

T = 296 K

0.18 × 0.09 × 0.07 mm

Data collection

Bruker SMART APEXII DUO CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.635, T max = 0.822

14048 measured reflections

3352 independent reflections

1593 reflections with I > 2σ(I)

R int = 0.074

Refinement

R[F 2 > 2σ(F 2)] = 0.052

wR(F 2) = 0.143

S = 1.01

3352 reflections

178 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.37 e Å−3

Δρmin = −0.57 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); 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 datablock(s) global, I. DOI: 10.1107/S1600536812034617/hb6926sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812034617/hb6926Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812034617/hb6926Isup3.cml

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

C16H16BrNO	F(000) = 648
Mr = 318.21	Dx = 1.440 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1376 reflections
a = 4.7146 (6) Å	θ = 3.0–20.1°
b = 22.999 (3) Å	µ = 2.79 mm−1
c = 13.5350 (15) Å	T = 296 K
β = 91.138 (3)°	Plate, colourless
V = 1467.3 (3) Å3	0.18 × 0.09 × 0.07 mm
Z = 4

Bruker SMART APEXII DUO CCD diffractometer	3352 independent reflections
Radiation source: fine-focus sealed tube	1593 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.074
φ and ω scans	θmax = 27.5°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −6→6
Tmin = 0.635, Tmax = 0.822	k = −26→29
14048 measured reflections	l = −17→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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.143	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ2(Fo2) + (0.0518P)2 + 0.539P] where P = (Fo2 + 2Fc2)/3
3352 reflections	(Δ/σ)max = 0.001
178 parameters	Δρmax = 0.37 e Å−3
0 restraints	Δρmin = −0.57 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	0.41005 (16)	0.35233 (3)	0.61576 (4)	0.1038 (3)
O1	0.4016 (5)	0.33510 (13)	1.1247 (2)	0.0615 (8)
N1	−0.0290 (7)	0.37234 (13)	1.1589 (2)	0.0416 (7)
C1	0.0074 (10)	0.35773 (19)	0.8830 (4)	0.0688 (13)
H1A	−0.1203	0.3825	0.9134	0.083*
C2	0.0970 (11)	0.3706 (2)	0.7894 (4)	0.0744 (14)
H2A	0.0300	0.4037	0.7570	0.089*
C3	0.2837 (10)	0.33480 (19)	0.7448 (3)	0.0614 (11)
C4	0.3828 (10)	0.28624 (19)	0.7918 (3)	0.0652 (12)
H4A	0.5100	0.2616	0.7609	0.078*
C5	0.2916 (9)	0.27413 (17)	0.8861 (3)	0.0550 (10)
H5A	0.3608	0.2413	0.9186	0.066*
C6	0.1019 (8)	0.30930 (17)	0.9327 (3)	0.0469 (9)
C7	0.0048 (8)	0.29567 (17)	1.0356 (3)	0.0531 (10)
H7A	0.0515	0.2557	1.0517	0.064*
H7B	−0.1996	0.3000	1.0383	0.064*
C8	0.1443 (8)	0.33567 (16)	1.1105 (3)	0.0464 (9)
C9	0.0737 (7)	0.41182 (15)	1.2329 (2)	0.0380 (8)
C10	0.2465 (8)	0.45805 (16)	1.2062 (3)	0.0477 (9)
C11	0.3468 (10)	0.49491 (18)	1.2805 (3)	0.0664 (12)
H11A	0.4670	0.5254	1.2645	0.080*
C12	0.2719 (10)	0.4871 (2)	1.3765 (3)	0.0704 (13)
H12A	0.3412	0.5122	1.4251	0.084*
C13	0.0963 (10)	0.4428 (2)	1.4010 (3)	0.0618 (12)
H13A	0.0450	0.4383	1.4666	0.074*
C14	−0.0091 (8)	0.40372 (16)	1.3301 (3)	0.0470 (9)
C15	0.3245 (11)	0.4697 (2)	1.1008 (3)	0.0736 (13)
H15A	0.1636	0.4621	1.0581	0.110*
H15B	0.4787	0.4448	1.0829	0.110*
H15C	0.3808	0.5096	1.0941	0.110*
C16	−0.2007 (10)	0.35451 (19)	1.3576 (3)	0.0680 (12)
H16A	−0.1351	0.3192	1.3278	0.102*
H16B	−0.3903	0.3627	1.3344	0.102*
H16C	−0.1992	0.3502	1.4281	0.102*
H1N1	−0.220 (8)	0.3663 (14)	1.153 (3)	0.042 (10)*

	U11	U22	U33	U12	U13	U23
Br1	0.1668 (7)	0.0908 (4)	0.0537 (3)	−0.0423 (4)	0.0020 (3)	0.0035 (3)
O1	0.0288 (15)	0.081 (2)	0.0748 (19)	0.0040 (14)	0.0040 (14)	−0.0234 (15)
N1	0.0260 (17)	0.0529 (19)	0.0457 (17)	0.0002 (15)	−0.0001 (15)	−0.0070 (14)
C1	0.063 (3)	0.064 (3)	0.079 (3)	0.022 (2)	−0.002 (3)	−0.012 (3)
C2	0.085 (4)	0.061 (3)	0.076 (3)	0.013 (3)	−0.014 (3)	0.008 (2)
C3	0.077 (3)	0.055 (3)	0.052 (2)	−0.015 (2)	−0.003 (2)	−0.005 (2)
C4	0.083 (3)	0.056 (3)	0.057 (3)	0.007 (2)	0.015 (3)	−0.011 (2)
C5	0.064 (3)	0.047 (2)	0.053 (2)	0.010 (2)	0.005 (2)	−0.0060 (18)
C6	0.038 (2)	0.050 (2)	0.053 (2)	−0.0018 (19)	−0.0050 (19)	−0.0126 (19)
C7	0.036 (2)	0.062 (3)	0.061 (2)	−0.0096 (19)	0.010 (2)	−0.021 (2)
C8	0.033 (2)	0.057 (2)	0.050 (2)	0.0006 (19)	0.0076 (19)	−0.0070 (18)
C9	0.0304 (19)	0.041 (2)	0.0421 (19)	0.0044 (16)	−0.0021 (17)	−0.0023 (16)
C10	0.047 (2)	0.044 (2)	0.052 (2)	0.0030 (19)	−0.0013 (19)	0.0040 (18)
C11	0.067 (3)	0.052 (3)	0.079 (3)	−0.009 (2)	−0.005 (3)	−0.010 (2)
C12	0.079 (3)	0.066 (3)	0.066 (3)	0.000 (3)	−0.011 (3)	−0.024 (2)
C13	0.071 (3)	0.074 (3)	0.040 (2)	0.016 (3)	0.000 (2)	−0.010 (2)
C14	0.042 (2)	0.052 (2)	0.048 (2)	0.0086 (19)	0.0069 (19)	0.0016 (18)
C15	0.090 (4)	0.069 (3)	0.062 (3)	−0.014 (3)	0.006 (3)	0.019 (2)
C16	0.061 (3)	0.084 (3)	0.059 (3)	0.002 (3)	0.017 (2)	0.010 (2)

Br1—C3	1.899 (4)	C7—H7B	0.9700
O1—C8	1.224 (4)	C9—C10	1.392 (5)
N1—C8	1.353 (5)	C9—C14	1.392 (5)
N1—C9	1.429 (4)	C10—C11	1.391 (5)
N1—H1N1	0.91 (4)	C10—C15	1.504 (5)
C1—C6	1.371 (6)	C11—C12	1.365 (6)
C1—C2	1.376 (6)	C11—H11A	0.9300
C1—H1A	0.9300	C12—C13	1.358 (6)
C2—C3	1.356 (6)	C12—H12A	0.9300
C2—H2A	0.9300	C13—C14	1.400 (5)
C3—C4	1.363 (6)	C13—H13A	0.9300
C4—C5	1.383 (5)	C14—C16	1.500 (5)
C4—H4A	0.9300	C15—H15A	0.9600
C5—C6	1.369 (5)	C15—H15B	0.9600
C5—H5A	0.9300	C15—H15C	0.9600
C6—C7	1.508 (5)	C16—H16A	0.9600
C7—C8	1.510 (5)	C16—H16B	0.9600
C7—H7A	0.9700	C16—H16C	0.9600
C8—N1—C9	122.4 (3)	C10—C9—C14	121.6 (3)
C8—N1—H1N1	118 (2)	C10—C9—N1	119.7 (3)
C9—N1—H1N1	118 (2)	C14—C9—N1	118.7 (3)
C6—C1—C2	121.6 (4)	C11—C10—C9	118.0 (4)
C6—C1—H1A	119.2	C11—C10—C15	119.4 (4)
C2—C1—H1A	119.2	C9—C10—C15	122.6 (4)
C3—C2—C1	119.5 (4)	C12—C11—C10	121.2 (4)
C3—C2—H2A	120.2	C12—C11—H11A	119.4
C1—C2—H2A	120.2	C10—C11—H11A	119.4
C2—C3—C4	120.6 (4)	C13—C12—C11	120.2 (4)
C2—C3—Br1	119.9 (4)	C13—C12—H12A	119.9
C4—C3—Br1	119.5 (3)	C11—C12—H12A	119.9
C3—C4—C5	119.1 (4)	C12—C13—C14	121.6 (4)
C3—C4—H4A	120.5	C12—C13—H13A	119.2
C5—C4—H4A	120.5	C14—C13—H13A	119.2
C6—C5—C4	121.6 (4)	C9—C14—C13	117.4 (4)
C6—C5—H5A	119.2	C9—C14—C16	121.2 (3)
C4—C5—H5A	119.2	C13—C14—C16	121.4 (4)
C5—C6—C1	117.6 (4)	C10—C15—H15A	109.5
C5—C6—C7	121.0 (4)	C10—C15—H15B	109.5
C1—C6—C7	121.3 (4)	H15A—C15—H15B	109.5
C6—C7—C8	110.9 (3)	C10—C15—H15C	109.5
C6—C7—H7A	109.5	H15A—C15—H15C	109.5
C8—C7—H7A	109.5	H15B—C15—H15C	109.5
C6—C7—H7B	109.5	C14—C16—H16A	109.5
C8—C7—H7B	109.5	C14—C16—H16B	109.5
H7A—C7—H7B	108.0	H16A—C16—H16B	109.5
O1—C8—N1	122.4 (3)	C14—C16—H16C	109.5
O1—C8—C7	121.1 (3)	H16A—C16—H16C	109.5
N1—C8—C7	116.5 (3)	H16B—C16—H16C	109.5
C6—C1—C2—C3	−0.1 (7)	C8—N1—C9—C10	67.8 (5)
C1—C2—C3—C4	0.1 (7)	C8—N1—C9—C14	−113.9 (4)
C1—C2—C3—Br1	−179.7 (3)	C14—C9—C10—C11	3.0 (5)
C2—C3—C4—C5	−0.4 (7)	N1—C9—C10—C11	−178.8 (3)
Br1—C3—C4—C5	179.4 (3)	C14—C9—C10—C15	−176.3 (4)
C3—C4—C5—C6	0.8 (7)	N1—C9—C10—C15	2.0 (5)
C4—C5—C6—C1	−0.9 (6)	C9—C10—C11—C12	−1.8 (6)
C4—C5—C6—C7	−179.8 (4)	C15—C10—C11—C12	177.4 (4)
C2—C1—C6—C5	0.5 (6)	C10—C11—C12—C13	0.0 (7)
C2—C1—C6—C7	179.5 (4)	C11—C12—C13—C14	0.9 (7)
C5—C6—C7—C8	104.8 (4)	C10—C9—C14—C13	−2.2 (5)
C1—C6—C7—C8	−74.1 (5)	N1—C9—C14—C13	179.6 (3)
C9—N1—C8—O1	−2.2 (6)	C10—C9—C14—C16	178.6 (4)
C9—N1—C8—C7	178.9 (3)	N1—C9—C14—C16	0.3 (5)
C6—C7—C8—O1	−63.7 (5)	C12—C13—C14—C9	0.2 (6)
C6—C7—C8—N1	115.2 (4)	C12—C13—C14—C16	179.4 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N1···O1i	0.91 (4)	1.95 (4)	2.847 (4)	166 (3)
C7—H7B···O1i	0.97	2.38	3.240 (5)	148

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N1⋯O1i	0.91 (4)	1.95 (4)	2.847 (4)	166 (3)
C7—H7B⋯O1i	0.97	2.38	3.240 (5)	148

Symmetry code: (i) .