N-(3-Bromo­phen­yl)acetamide

Gowda, B.T.; Foro, S.; Terao, H.; Fuess, H.

doi:10.1107/S1600536809013294

organic compounds

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ISSN: 2056-9890

Volume 65| Part 5| May 2009| Page o1039

doi:10.1107/S1600536809013294

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N-(3-Bromophenyl)acetamide

B. Thimme Gowda,^a ^* Sabine Foro,^b Hiromitsu Terao ^c and Hartmut Fuess ^b

^aDepartment of Chemistry, Mangalore University, Mangalagangotri 574 199, Mangalore, India, ^bInstitute of Materials Science, Darmstadt University of Technology, Petersenstrasse 23, D-64287 Darmstadt, Germany, and ^cFaculty of Integrated Arts and Sciences, Tokushima University, Minamijosanjima-cho, Tokushima 770-8502, Japan
^*Correspondence e-mail: gowdabt@yahoo.com

(Received 6 April 2009; accepted 7 April 2009; online 18 April 2009)

The conformation of the N—H bond in the structure of the title compound, C₈H₈BrNO, is anti to the C=O bond and to the meta-bromo substituent of the aromatic ring in both independent molecules comprising the asymmetric unit. Molecules are linked through N—H⋯O hydrogen bonding into supramolecular chains with a twisted topology.

Related literature

For the preparation of the compound, see: Gowda et al. (2006 ). For related structures, see: Gowda et al. (2007 , 2008 , 2009 ).

Experimental

Crystal data

C₈H₈BrNO
M_r = 214.06
Orthorhombic, P 2₁ 2₁ 2₁
a = 4.7836 (6) Å
b = 18.765 (1) Å
c = 19.379 (2) Å
V = 1739.5 (3) Å³
Z = 8
Mo Kα radiation
μ = 4.67 mm⁻¹
T = 299 K
0.44 × 0.10 × 0.08 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007 $[Oxford Diffraction (2007). CrysAlis RED. Oxford Diffraction Ltd, Köln, Germany.]$ ) T_min = 0.226, T_max = 0.685
9612 measured reflections
3449 independent reflections
2043 reflections with I > 2σ(I)
R_int = 0.034

Refinement

R[F² > 2σ(F²)] = 0.045
wR(F²) = 0.093
S = 0.99
3449 reflections
201 parameters
H-atom parameters constrained
Δρ_max = 0.31 e Å⁻³
Δρ_min = −0.49 e Å⁻³
Absolute structure: Flack (1983 ), 1366 Friedel pairs
Flack parameter: −0.008 (13)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O2ⁱ	0.86	2.05	2.887 (5)	166
N2—H2N⋯O1	0.86	2.10	2.953 (5)	169
Symmetry code: (i) $[-x+2, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: CrysAlis CCD (Oxford Diffraction, 2004 $[Oxford Diffraction (2004). CrysAlis CCD. Oxford Diffraction Ltd, Köln, Germany.]$ ); cell refinement: CrysAlis RED (Oxford Diffraction, 2007 $[Oxford Diffraction (2007). CrysAlis RED. Oxford Diffraction Ltd, Köln, Germany.]$ ); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809013294/tk2417sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809013294/tk2417Isup2.hkl

checkCIF report

Comment top

As part of a study of the effect of ring and side-chain substitutions on the crystal structures of aromatic amides (Gowda et al., 2007, 2008, 2009), in the present work, the structure of N-(3-bromophenyl)acetamide (I) has been determined. The conformation of the N—H bond in the structure is anti to the meta-bromo substituent of the aromatic ring (Fig. 1), in both independent molecules comprising the asymmetric unit, similar to that observed in N-(3-chlorophenyl)acetamide (Gowda et al., 2008). Further, the conformation of the C=O bond is anti to the N—H bond. The two independent molecules in (I) are linked through intermolecular N—H···O hydrogen bonding into a supramolecular chains with a twisted topology (Table 1, Fig. 2).

Related literature top

For the preparation of the compound, see: Gowda et al. (2006). For related structures, see: Gowda et al. (2007, 2008, 2009)

Experimental top

Compound (I) was prepared according to the literature method (Gowda et al., 2006). Single crystals were obtained from an ethanolic solution of (I).

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2004); cell refinement: CrysAlis RED (Oxford Diffraction, 2007); data reduction: CrysAlis RED (Oxford Diffraction, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. Molecular structure of (I), showing the atom labeling scheme and displacement ellipsoids drawn at the 50% probability level. The intermolecular N-H···O hydrogen is shown as a dashed line.
	Fig. 2. Molecular packing of (I) viewed in projection down the a-axis highlighting the supramolecular chains mediated by hydrogen bonding (shown as dashed lines).

N-(3-Bromophenyl)acetamide top

Crystal data top

C₈H₈BrNO	F(000) = 848
M_r = 214.06	D_x = 1.635 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 3601 reflections
a = 4.7836 (6) Å	θ = 2.4–27.6°
b = 18.765 (1) Å	µ = 4.67 mm⁻¹
c = 19.379 (2) Å	T = 299 K
V = 1739.5 (3) Å³	Long needle, colourless
Z = 8	0.44 × 0.10 × 0.08 mm

Data collection top

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	3449 independent reflections
Radiation source: fine-focus sealed tube	2043 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.034
Rotation method data acquisition using ω and ϕ scans	θ_max = 26.4°, θ_min = 2.4°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007)	h = −5→5
T_min = 0.226, T_max = 0.685	k = −22→23
9612 measured reflections	l = −20→24

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.045	H-atom parameters constrained
wR(F²) = 0.093	w = 1/[σ²(F_o²) + (0.0455P)² + 0.0252P] where P = (F_o² + 2F_c²)/3
S = 0.99	(Δ/σ)_max = 0.001
3449 reflections	Δρ_max = 0.31 e Å⁻³
201 parameters	Δρ_min = −0.49 e Å⁻³
0 restraints	Absolute structure: Flack (1983), 1366 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.008 (13)

Crystal data top

C₈H₈BrNO	V = 1739.5 (3) Å³
M_r = 214.06	Z = 8
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 4.7836 (6) Å	µ = 4.67 mm⁻¹
b = 18.765 (1) Å	T = 299 K
c = 19.379 (2) Å	0.44 × 0.10 × 0.08 mm

Data collection top

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	3449 independent reflections
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007)	2043 reflections with I > 2σ(I)
T_min = 0.226, T_max = 0.685	R_int = 0.034
9612 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	H-atom parameters constrained
wR(F²) = 0.093	Δρ_max = 0.31 e Å⁻³
S = 0.99	Δρ_min = −0.49 e Å⁻³
3449 reflections	Absolute structure: Flack (1983), 1366 Friedel pairs
201 parameters	Absolute structure parameter: −0.008 (13)
0 restraints

Special details top

Experimental. Absorption correction: CrysAlis RED, Oxford Diffraction Ltd. (2007). Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Br1	0.64658 (17)	0.36438 (3)	0.40336 (3)	0.0961 (3)
O1	1.0611 (8)	0.22271 (18)	0.20168 (19)	0.0786 (12)
N1	0.9531 (7)	0.13129 (19)	0.27225 (19)	0.0531 (10)
H1N	0.9782	0.0863	0.2779	0.064*
C1	0.7804 (10)	0.1647 (2)	0.3206 (2)	0.0492 (12)
C2	0.7903 (10)	0.2377 (2)	0.3338 (2)	0.0524 (12)
H2	0.9111	0.2670	0.3092	0.063*
C3	0.6192 (12)	0.2656 (3)	0.3838 (2)	0.0606 (14)
C4	0.4398 (12)	0.2247 (4)	0.4216 (3)	0.0740 (17)
H4	0.3269	0.2450	0.4553	0.089*
C5	0.4300 (12)	0.1519 (3)	0.4084 (3)	0.0848 (18)
H5	0.3068	0.1234	0.4331	0.102*
C6	0.6000 (11)	0.1215 (3)	0.3592 (3)	0.0691 (15)
H6	0.5951	0.0726	0.3516	0.083*
C7	1.0850 (10)	0.1608 (3)	0.2180 (2)	0.0546 (13)
C8	1.2664 (11)	0.1102 (2)	0.1767 (2)	0.0726 (17)
H8A	1.2240	0.0620	0.1895	0.087*
H8B	1.4597	0.1199	0.1861	0.087*
H8C	1.2303	0.1166	0.1284	0.087*
Br2	0.30944 (16)	0.49664 (3)	−0.03009 (3)	0.0919 (3)
O2	0.9050 (8)	0.48750 (17)	0.18809 (18)	0.0709 (10)
N2	0.8933 (8)	0.36972 (18)	0.16644 (18)	0.0475 (9)
H2N	0.9634	0.3294	0.1785	0.057*
C9	0.6865 (9)	0.3675 (2)	0.11456 (19)	0.0397 (10)
C10	0.6162 (10)	0.4252 (2)	0.0737 (2)	0.0464 (11)
H10	0.7039	0.4690	0.0799	0.056*
C11	0.4147 (10)	0.4168 (2)	0.0239 (2)	0.0499 (12)
C12	0.2819 (9)	0.3533 (3)	0.0127 (2)	0.0528 (12)
H12	0.1476	0.3489	−0.0218	0.063*
C13	0.3519 (12)	0.2959 (3)	0.0536 (2)	0.0576 (13)
H13	0.2619	0.2525	0.0473	0.069*
C14	0.5532 (9)	0.3025 (2)	0.1035 (2)	0.0490 (12)
H14	0.6013	0.2632	0.1302	0.059*
C15	0.9939 (9)	0.4277 (3)	0.1993 (2)	0.0490 (12)
C16	1.2135 (10)	0.4133 (3)	0.2521 (3)	0.0652 (14)
H16A	1.2663	0.3640	0.2502	0.078*
H16B	1.1416	0.4242	0.2971	0.078*
H16C	1.3739	0.4426	0.2429	0.078*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.1400 (6)	0.0715 (4)	0.0768 (4)	0.0319 (4)	−0.0121 (4)	−0.0259 (3)
O1	0.110 (3)	0.046 (2)	0.080 (2)	0.013 (2)	0.022 (2)	0.0251 (19)
N1	0.067 (3)	0.035 (2)	0.057 (2)	0.0055 (19)	0.003 (2)	0.012 (2)
C1	0.058 (3)	0.045 (3)	0.044 (3)	0.005 (2)	−0.005 (2)	0.006 (2)
C2	0.065 (3)	0.045 (3)	0.047 (2)	0.004 (2)	−0.003 (3)	0.003 (2)
C3	0.075 (4)	0.064 (3)	0.043 (3)	0.021 (3)	−0.007 (3)	−0.006 (3)
C4	0.068 (4)	0.108 (5)	0.046 (3)	0.021 (3)	0.008 (3)	−0.009 (3)
C5	0.089 (5)	0.096 (5)	0.070 (4)	−0.020 (3)	0.014 (4)	0.002 (4)
C6	0.083 (4)	0.059 (3)	0.065 (3)	−0.009 (3)	0.003 (3)	0.009 (3)
C7	0.067 (4)	0.045 (3)	0.052 (3)	0.007 (2)	0.002 (3)	0.008 (2)
C8	0.086 (5)	0.065 (3)	0.066 (3)	0.005 (3)	0.012 (3)	0.002 (3)
Br2	0.1222 (5)	0.0670 (4)	0.0866 (4)	0.0074 (4)	−0.0273 (4)	0.0277 (3)
O2	0.091 (3)	0.0351 (18)	0.086 (2)	0.0039 (19)	−0.014 (2)	−0.0108 (17)
N2	0.058 (3)	0.0299 (19)	0.054 (2)	0.0034 (19)	0.000 (2)	0.0001 (18)
C9	0.044 (3)	0.035 (2)	0.040 (2)	0.000 (2)	0.004 (2)	−0.003 (2)
C10	0.051 (3)	0.035 (2)	0.053 (3)	−0.002 (2)	−0.001 (3)	0.005 (2)
C11	0.059 (3)	0.044 (3)	0.047 (3)	0.008 (2)	0.003 (3)	0.007 (2)
C12	0.048 (3)	0.058 (3)	0.052 (3)	−0.002 (2)	−0.003 (2)	−0.006 (2)
C13	0.056 (3)	0.051 (3)	0.066 (3)	−0.002 (3)	−0.007 (3)	−0.011 (3)
C14	0.053 (3)	0.035 (3)	0.058 (3)	0.000 (2)	0.006 (3)	−0.002 (2)
C15	0.050 (3)	0.047 (3)	0.050 (3)	−0.001 (3)	−0.001 (3)	−0.007 (3)
C16	0.065 (4)	0.062 (3)	0.069 (3)	−0.009 (3)	−0.007 (3)	−0.012 (3)

Geometric parameters (Å, º) top

Br1—C3	1.897 (5)	Br2—C11	1.895 (4)
O1—C7	1.209 (5)	O2—C15	1.220 (5)
N1—C7	1.346 (5)	N2—C15	1.349 (5)
N1—C1	1.398 (5)	N2—C9	1.411 (5)
N1—H1N	0.8600	N2—H2N	0.8600
C1—C2	1.394 (6)	C9—C10	1.383 (5)
C1—C6	1.400 (6)	C9—C14	1.392 (6)
C2—C3	1.372 (6)	C10—C11	1.374 (6)
C2—H2	0.9300	C10—H10	0.9300
C3—C4	1.364 (7)	C11—C12	1.369 (6)
C4—C5	1.390 (7)	C12—C13	1.377 (6)
C4—H4	0.9300	C12—H12	0.9300
C5—C6	1.377 (7)	C13—C14	1.371 (6)
C5—H5	0.9300	C13—H13	0.9300
C6—H6	0.9300	C14—H14	0.9300
C7—C8	1.514 (6)	C15—C16	1.490 (6)
C8—H8A	0.9600	C16—H16A	0.9600
C8—H8B	0.9600	C16—H16B	0.9600
C8—H8C	0.9600	C16—H16C	0.9600

C7—N1—C1	128.1 (4)	C15—N2—C9	127.6 (4)
C7—N1—H1N	116.0	C15—N2—H2N	116.2
C1—N1—H1N	116.0	C9—N2—H2N	116.2
C2—C1—N1	123.0 (4)	C10—C9—C14	119.1 (4)
C2—C1—C6	119.5 (5)	C10—C9—N2	123.7 (4)
N1—C1—C6	117.5 (4)	C14—C9—N2	117.2 (4)
C3—C2—C1	119.0 (5)	C11—C10—C9	118.9 (4)
C3—C2—H2	120.5	C11—C10—H10	120.5
C1—C2—H2	120.5	C9—C10—H10	120.5
C4—C3—C2	122.7 (5)	C12—C11—C10	122.5 (4)
C4—C3—Br1	119.1 (4)	C12—C11—Br2	118.5 (4)
C2—C3—Br1	118.2 (4)	C10—C11—Br2	119.0 (3)
C3—C4—C5	118.3 (5)	C11—C12—C13	118.4 (4)
C3—C4—H4	120.8	C11—C12—H12	120.8
C5—C4—H4	120.8	C13—C12—H12	120.8
C6—C5—C4	121.0 (5)	C14—C13—C12	120.4 (4)
C6—C5—H5	119.5	C14—C13—H13	119.8
C4—C5—H5	119.5	C12—C13—H13	119.8
C5—C6—C1	119.6 (5)	C13—C14—C9	120.6 (4)
C5—C6—H6	120.2	C13—C14—H14	119.7
C1—C6—H6	120.2	C9—C14—H14	119.7
O1—C7—N1	123.7 (4)	O2—C15—N2	122.2 (4)
O1—C7—C8	121.3 (4)	O2—C15—C16	122.3 (4)
N1—C7—C8	115.0 (4)	N2—C15—C16	115.5 (4)
C7—C8—H8A	109.5	C15—C16—H16A	109.5
C7—C8—H8B	109.5	C15—C16—H16B	109.5
H8A—C8—H8B	109.5	H16A—C16—H16B	109.5
C7—C8—H8C	109.5	C15—C16—H16C	109.5
H8A—C8—H8C	109.5	H16A—C16—H16C	109.5
H8B—C8—H8C	109.5	H16B—C16—H16C	109.5

C7—N1—C1—C2	−22.3 (7)	C15—N2—C9—C10	21.5 (6)
C7—N1—C1—C6	160.8 (4)	C15—N2—C9—C14	−160.2 (4)
N1—C1—C2—C3	−177.9 (4)	C14—C9—C10—C11	0.7 (6)
C6—C1—C2—C3	−1.0 (7)	N2—C9—C10—C11	178.9 (4)
C1—C2—C3—C4	0.4 (7)	C9—C10—C11—C12	−0.5 (7)
C1—C2—C3—Br1	177.6 (3)	C9—C10—C11—Br2	178.0 (3)
C2—C3—C4—C5	−0.4 (8)	C10—C11—C12—C13	0.7 (7)
Br1—C3—C4—C5	−177.6 (4)	Br2—C11—C12—C13	−177.8 (4)
C3—C4—C5—C6	1.0 (8)	C11—C12—C13—C14	−1.1 (7)
C4—C5—C6—C1	−1.7 (8)	C12—C13—C14—C9	1.2 (7)
C2—C1—C6—C5	1.7 (7)	C10—C9—C14—C13	−1.0 (6)
N1—C1—C6—C5	178.7 (4)	N2—C9—C14—C13	−179.4 (4)
C1—N1—C7—O1	−3.1 (8)	C9—N2—C15—O2	2.2 (7)
C1—N1—C7—C8	177.9 (4)	C9—N2—C15—C16	−179.9 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O2ⁱ	0.86	2.05	2.887 (5)	166
N2—H2N···O1	0.86	2.10	2.953 (5)	169

Symmetry code: (i) −x+2, y−1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₈H₈BrNO
M_r	214.06
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	299
a, b, c (Å)	4.7836 (6), 18.765 (1), 19.379 (2)
V (Å³)	1739.5 (3)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	4.67
Crystal size (mm)	0.44 × 0.10 × 0.08

Data collection
Diffractometer	Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector
Absorption correction	Multi-scan (CrysAlis RED; Oxford Diffraction, 2007)
T_min, T_max	0.226, 0.685
No. of measured, independent and observed [I > 2σ(I)] reflections	9612, 3449, 2043
R_int	0.034
(sin θ/λ)_max (Å⁻¹)	0.626

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.093, 0.99
No. of reflections	3449
No. of parameters	201
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.31, −0.49
Absolute structure	Flack (1983), 1366 Friedel pairs
Absolute structure parameter	−0.008 (13)

Computer programs: CrysAlis CCD (Oxford Diffraction, 2004), CrysAlis RED (Oxford Diffraction, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O2ⁱ	0.86	2.05	2.887 (5)	166
N2—H2N···O1	0.86	2.10	2.953 (5)	169

Symmetry code: (i) −x+2, y−1/2, −z+1/2.

References

Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
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Gowda, B. T., Svoboda, I. & Fuess, H. (2007). Acta Cryst. E63, o3267. Web of Science CSD CrossRef IUCr Journals Google Scholar
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ISSN: 2056-9890

Volume 65| Part 5| May 2009| Page o1039

doi:10.1107/S1600536809013294

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