N-(4-Bromo-phen-yl)acetamide: a new polymorph.

A new polymorph of the title compound, C8H8BrNO, has been determined at 173 K in the space group P21/c. The previous room-temperature structure was reported to crystallize in the ortho-rhom-bic space group Pna21 [Andreetti et al. (1968 ▶). Acta Cryst. B24, 1195-1198]. In the crystal, mol-ecules are linked by N-H⋯O hydrogen bonds forming chains along [010]. Weak C-H⋯π inter-actions are also present.

Related literature

For 2-aryl­acetamides, see: Mijin & Marinkovic (2006 ▶); Mijin et al. (2008 ▶) and for amides, see: Wu et al. (2008 ▶, 2010 ▶). For the structure of the ortho­rhom­bic polymorph, see: Andreetti et al. (1968 ▶). For related structures, see: Praveen et al. (2011a ▶,b ▶,c ▶). For standard bond lengths, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C8H8BrNO

M = 214.06

Monoclinic,

a = 6.7250 (7) Å

b = 9.3876 (11) Å

c = 14.4434 (14) Å

β = 117.750 (4)°

V = 806.96 (15) Å3

Z = 4

Mo Kα radiation

μ = 5.03 mm−1

T = 173 K

0.32 × 0.22 × 0.18 mm

Data collection

Oxford Diffraction Xcalibur (Eos, Gemini) diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction 2010 ▶) T min = 0.296, T max = 0.465

10902 measured reflections

2689 independent reflections

2099 reflections with I > 2σ(I)

R int = 0.035

Refinement

R[F 2 > 2σ(F 2)] = 0.033

wR(F 2) = 0.073

S = 1.04

2689 reflections

101 parameters

H-atom parameters constrained

Δρmax = 0.54 e Å−3

Δρmin = −0.44 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Oxford Diffraction, 2010 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813005448/su2566sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813005448/su2566Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813005448/su2566Isup3.cml

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

C8H8BrNO	F(000) = 424
Mr = 214.06	Dx = 1.762 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3269 reflections
a = 6.7250 (7) Å	θ = 3.4–32.3°
b = 9.3876 (11) Å	µ = 5.03 mm−1
c = 14.4434 (14) Å	T = 173 K
β = 117.750 (4)°	Block, yellow
V = 806.96 (15) Å3	0.32 × 0.22 × 0.18 mm
Z = 4

Oxford Diffraction Xcalibur (Eos, Gemini) diffractometer	2689 independent reflections
Radiation source: Enhance (Mo) X-ray Source	2099 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.035
Detector resolution: 16.1500 pixels mm-1	θmax = 32.3°, θmin = 3.4°
ω scans	h = −9→9
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction 2010)	k = −13→13
Tmin = 0.296, Tmax = 0.465	l = −20→19
10902 measured reflections

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)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.073	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0329P)2 + 0.1779P] where P = (Fo2 + 2Fc2)/3
2689 reflections	(Δ/σ)max = 0.001
101 parameters	Δρmax = 0.54 e Å−3
0 restraints	Δρmin = −0.44 e Å−3

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.

	x	y	z	Uiso*/Ueq
Br1	−0.12616 (4)	0.70900 (2)	0.493749 (17)	0.03329 (8)
O1	0.4333 (2)	0.63844 (14)	0.19611 (11)	0.0286 (3)
N1	0.3872 (3)	0.85329 (15)	0.25584 (12)	0.0212 (3)
H1	0.4358	0.9432	0.2658	0.025*
C1	0.5678 (4)	0.8449 (2)	0.14665 (17)	0.0283 (4)
H1A	0.5162	0.8041	0.0767	0.042*
H1B	0.7312	0.8344	0.1869	0.042*
H1C	0.5281	0.9462	0.1404	0.042*
C2	0.4570 (3)	0.76819 (19)	0.20162 (15)	0.0213 (4)
C3	0.2696 (3)	0.81333 (18)	0.31030 (14)	0.0199 (3)
C4	0.2647 (3)	0.91062 (19)	0.38173 (15)	0.0240 (4)
H4	0.3428	0.9985	0.3931	0.029*
C5	0.1473 (3)	0.8806 (2)	0.43633 (16)	0.0265 (4)
H5	0.1435	0.9475	0.4849	0.032*
C6	0.0351 (3)	0.7520 (2)	0.41948 (15)	0.0233 (4)
C7	0.0369 (3)	0.6541 (2)	0.34821 (15)	0.0247 (4)
H7	−0.0407	0.5662	0.3374	0.030*
C8	0.1522 (3)	0.68544 (19)	0.29313 (15)	0.0235 (4)
H8	0.1518	0.6195	0.2431	0.028*

	U11	U22	U33	U12	U13	U23
Br1	0.03360 (13)	0.03978 (14)	0.03455 (13)	−0.00199 (9)	0.02264 (10)	0.00392 (9)
O1	0.0383 (8)	0.0163 (6)	0.0388 (8)	0.0038 (6)	0.0242 (7)	−0.0003 (5)
N1	0.0257 (8)	0.0132 (7)	0.0290 (8)	−0.0018 (6)	0.0163 (7)	−0.0016 (6)
C1	0.0328 (11)	0.0252 (9)	0.0350 (11)	0.0002 (8)	0.0226 (9)	−0.0001 (8)
C2	0.0214 (9)	0.0189 (9)	0.0260 (9)	0.0025 (7)	0.0129 (7)	0.0009 (7)
C3	0.0207 (9)	0.0161 (8)	0.0237 (9)	0.0028 (6)	0.0109 (7)	0.0020 (6)
C4	0.0296 (10)	0.0159 (8)	0.0288 (10)	−0.0009 (7)	0.0157 (8)	−0.0008 (7)
C5	0.0331 (11)	0.0219 (9)	0.0285 (10)	0.0009 (8)	0.0176 (9)	−0.0028 (7)
C6	0.0213 (9)	0.0263 (9)	0.0239 (9)	0.0019 (7)	0.0119 (8)	0.0050 (7)
C7	0.0239 (9)	0.0204 (8)	0.0301 (10)	−0.0038 (7)	0.0129 (8)	−0.0001 (7)
C8	0.0257 (9)	0.0182 (8)	0.0281 (10)	−0.0014 (7)	0.0138 (8)	−0.0027 (7)

Br1—C6	1.8906 (19)	C3—C8	1.394 (2)
O1—C2	1.226 (2)	C4—C5	1.380 (3)
N1—C2	1.347 (2)	C4—H4	0.9500
N1—C3	1.401 (2)	C5—C6	1.384 (3)
N1—H1	0.8922	C5—H5	0.9500
C1—C2	1.501 (3)	C6—C7	1.384 (3)
C1—H1A	0.9800	C7—C8	1.377 (3)
C1—H1B	0.9800	C7—H7	0.9500
C1—H1C	0.9800	C8—H8	0.9500
C3—C4	1.390 (2)
C2—N1—C3	127.45 (15)	C5—C4—C3	120.52 (17)
C2—N1—H1	117.0	C5—C4—H4	119.7
C3—N1—H1	115.1	C3—C4—H4	119.7
C2—C1—H1A	109.5	C4—C5—C6	119.17 (17)
C2—C1—H1B	109.5	C4—C5—H5	120.4
H1A—C1—H1B	109.5	C6—C5—H5	120.4
C2—C1—H1C	109.5	C5—C6—C7	121.18 (18)
H1A—C1—H1C	109.5	C5—C6—Br1	119.76 (15)
H1B—C1—H1C	109.5	C7—C6—Br1	119.06 (15)
O1—C2—N1	123.83 (17)	C8—C7—C6	119.33 (18)
O1—C2—C1	121.58 (17)	C8—C7—H7	120.3
N1—C2—C1	114.59 (16)	C6—C7—H7	120.3
C4—C3—C8	119.39 (18)	C7—C8—C3	120.39 (18)
C4—C3—N1	117.09 (16)	C7—C8—H8	119.8
C8—C3—N1	123.46 (17)	C3—C8—H8	119.8
C3—N1—C2—O1	−3.1 (3)	C4—C5—C6—C7	−0.7 (3)
C3—N1—C2—C1	176.68 (18)	C4—C5—C6—Br1	179.88 (15)
C2—N1—C3—C4	164.06 (18)	C5—C6—C7—C8	0.0 (3)
C2—N1—C3—C8	−18.6 (3)	Br1—C6—C7—C8	179.37 (15)
C8—C3—C4—C5	0.8 (3)	C6—C7—C8—C3	1.2 (3)
N1—C3—C4—C5	178.23 (17)	C4—C3—C8—C7	−1.6 (3)
C3—C4—C5—C6	0.3 (3)	N1—C3—C8—C7	−178.81 (18)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1i	0.89	2.00	2.885 (2)	174
C1—H1B···Cg1ii	0.98	2.84	3.761 (3)	157

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C3–C8 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1i	0.89	2.00	2.885 (2)	174
C1—H1B⋯Cg1ii	0.98	2.84	3.761 (3)	157

Symmetry codes: (i) ; (ii) .