N-(2-Bromo-phen-yl)-2-(naphthalen-1-yl)acetamide.

In the title compound, C(18)H(14)BrNO, the naphthalene ring system [maximum deviation = 0.015 (3) Å] forms a dihedral angle of 67.70 (10)° with the benzene ring. In the crystal, mol-ecules are linked by N-H⋯O hydrogen bonds into C(4) chains propagating in [100]. A C-H⋯O inter-action reinforces the chain connectivity, generating an R(2) (1)(6) loop.

Related literature

For general background to and related structures of the title compound, see: Fun et al. (2010 ▶, 2011a ▶,b ▶, 2012 ▶). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C18H14BrNO

M = 340.21

Orthorhombic,

a = 4.7603 (1) Å

b = 11.4614 (3) Å

c = 26.6255 (6) Å

V = 1452.68 (6) Å3

Z = 4

Mo Kα radiation

μ = 2.83 mm−1

T = 100 K

0.32 × 0.16 × 0.13 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.463, T max = 0.719

16642 measured reflections

3864 independent reflections

3516 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.029

wR(F 2) = 0.061

S = 1.03

3864 reflections

195 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.63 e Å−3

Δρmin = −0.33 e Å−3

Absolute structure: Flack (1983 ▶), 1587 Friedel pairs

Flack parameter: 0.001 (8)

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/S1600536812034423/hb6923sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812034423/hb6923Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812034423/hb6923Isup3.cml

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

C18H14BrNO	F(000) = 688
Mr = 340.21	Dx = 1.556 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 8019 reflections
a = 4.7603 (1) Å	θ = 2.3–30.8°
b = 11.4614 (3) Å	µ = 2.83 mm−1
c = 26.6255 (6) Å	T = 100 K
V = 1452.68 (6) Å3	Block, colourless
Z = 4	0.32 × 0.16 × 0.13 mm

Bruker SMART APEXII CCD diffractometer	3864 independent reflections
Radiation source: fine-focus sealed tube	3516 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.031
φ and ω scans	θmax = 29.0°, θmin = 1.5°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −6→6
Tmin = 0.463, Tmax = 0.719	k = −15→15
16642 measured reflections	l = −36→36

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)] = 0.029	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.061	w = 1/[σ2(Fo2) + (0.0272P)2 + 0.2223P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max = 0.001
3864 reflections	Δρmax = 0.63 e Å−3
195 parameters	Δρmin = −0.33 e Å−3
0 restraints	Absolute structure: Flack (1983), 1587 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.001 (8)

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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	0.44680 (5)	0.197949 (18)	0.766005 (8)	0.01881 (6)
O1	1.1551 (4)	0.32404 (15)	0.64580 (7)	0.0288 (4)
N1	0.7212 (5)	0.25292 (18)	0.66352 (8)	0.0205 (4)
C1	0.9798 (6)	0.4924 (2)	0.54712 (8)	0.0243 (5)
C2	0.8336 (6)	0.3968 (2)	0.52540 (10)	0.0290 (6)
H2A	0.7122	0.3512	0.5458	0.035*
C3	0.8643 (7)	0.3692 (3)	0.47576 (10)	0.0362 (7)
H3A	0.7616	0.3060	0.4618	0.043*
C4	1.0465 (8)	0.4340 (3)	0.44572 (10)	0.0404 (7)
H4A	1.0702	0.4133	0.4114	0.048*
C5	1.1896 (7)	0.5257 (3)	0.46455 (10)	0.0342 (7)
H5A	1.3099	0.5691	0.4431	0.041*
C6	1.1646 (6)	0.5586 (2)	0.51556 (9)	0.0254 (5)
C7	1.3132 (7)	0.6544 (2)	0.53578 (11)	0.0327 (6)
H7A	1.4370	0.6981	0.5151	0.039*
C8	1.2791 (6)	0.6844 (2)	0.58521 (10)	0.0318 (6)
H8A	1.3788	0.7488	0.5989	0.038*
C9	1.0935 (6)	0.6184 (2)	0.61591 (9)	0.0274 (6)
H9A	1.0688	0.6408	0.6500	0.033*
C10	0.9508 (6)	0.52492 (19)	0.59833 (8)	0.0237 (5)
C11	0.7656 (6)	0.45304 (19)	0.63269 (9)	0.0238 (5)
H11A	0.5846	0.4374	0.6156	0.029*
H11B	0.7254	0.4984	0.6635	0.029*
C12	0.9006 (6)	0.3379 (2)	0.64713 (8)	0.0211 (6)
C13	0.8129 (5)	0.14552 (19)	0.68404 (8)	0.0169 (5)
C14	0.7098 (5)	0.10589 (17)	0.73006 (8)	0.0159 (4)
C15	0.7974 (5)	0.00074 (19)	0.75029 (8)	0.0202 (5)
H15A	0.7212	−0.0260	0.7812	0.024*
C16	0.9963 (5)	−0.06519 (18)	0.72528 (8)	0.0244 (6)
H16A	1.0604	−0.1365	0.7394	0.029*
C17	1.1024 (5)	−0.0273 (2)	0.67953 (9)	0.0240 (6)
H17A	1.2386	−0.0729	0.6623	0.029*
C18	1.0100 (5)	0.07691 (19)	0.65886 (8)	0.0207 (5)
H18A	1.0815	0.1018	0.6273	0.025*
H1N1	0.543 (6)	0.261 (2)	0.6612 (8)	0.015 (6)*

	U11	U22	U33	U12	U13	U23
Br1	0.01624 (11)	0.01879 (9)	0.02138 (9)	0.00023 (10)	0.00331 (10)	0.00085 (8)
O1	0.0139 (9)	0.0299 (10)	0.0427 (10)	0.0035 (8)	0.0034 (9)	0.0116 (8)
N1	0.0126 (11)	0.0246 (10)	0.0244 (9)	0.0045 (9)	0.0025 (10)	0.0081 (8)
C1	0.0171 (14)	0.0310 (11)	0.0249 (10)	0.0080 (11)	−0.0005 (11)	0.0072 (9)
C2	0.0178 (13)	0.0312 (13)	0.0380 (14)	0.0009 (12)	−0.0006 (13)	0.0094 (11)
C3	0.0269 (17)	0.0460 (16)	0.0359 (14)	0.0036 (14)	−0.0049 (13)	−0.0062 (12)
C4	0.0273 (15)	0.0627 (19)	0.0312 (12)	0.0067 (18)	0.0001 (15)	−0.0022 (12)
C5	0.0229 (15)	0.0514 (17)	0.0282 (13)	0.0013 (14)	0.0047 (13)	0.0095 (12)
C6	0.0188 (13)	0.0313 (13)	0.0261 (11)	0.0052 (12)	0.0023 (12)	0.0084 (10)
C7	0.0226 (15)	0.0352 (13)	0.0404 (14)	0.0043 (13)	0.0041 (13)	0.0134 (11)
C8	0.0249 (15)	0.0285 (14)	0.0419 (14)	−0.0021 (13)	−0.0034 (12)	0.0033 (11)
C9	0.0242 (17)	0.0307 (12)	0.0271 (11)	0.0073 (12)	0.0011 (12)	0.0060 (9)
C10	0.0189 (12)	0.0245 (11)	0.0278 (10)	0.0071 (12)	0.0013 (13)	0.0058 (8)
C11	0.0214 (15)	0.0234 (11)	0.0264 (11)	0.0057 (11)	0.0021 (11)	0.0045 (9)
C12	0.0202 (16)	0.0237 (11)	0.0195 (10)	0.0030 (10)	0.0020 (11)	0.0028 (8)
C13	0.0116 (12)	0.0168 (10)	0.0222 (10)	−0.0002 (9)	−0.0031 (10)	0.0016 (8)
C14	0.0123 (11)	0.0158 (9)	0.0197 (9)	−0.0006 (8)	−0.0020 (11)	−0.0013 (8)
C15	0.0157 (12)	0.0187 (10)	0.0262 (10)	−0.0041 (10)	−0.0027 (10)	0.0052 (8)
C16	0.0170 (15)	0.0169 (10)	0.0393 (13)	−0.0006 (9)	−0.0036 (12)	0.0034 (8)
C17	0.0140 (15)	0.0231 (11)	0.0349 (12)	0.0026 (10)	−0.0006 (11)	−0.0088 (9)
C18	0.0146 (15)	0.0267 (11)	0.0210 (9)	0.0031 (10)	−0.0019 (10)	−0.0022 (8)

Br1—C14	1.896 (2)	C8—C9	1.422 (4)
O1—C12	1.223 (3)	C8—H8A	0.9500
N1—C12	1.367 (3)	C9—C10	1.352 (4)
N1—C13	1.416 (3)	C9—H9A	0.9500
N1—H1N1	0.86 (3)	C10—C11	1.514 (3)
C1—C10	1.420 (3)	C11—C12	1.517 (3)
C1—C2	1.421 (4)	C11—H11A	0.9900
C1—C6	1.434 (3)	C11—H11B	0.9900
C2—C3	1.367 (4)	C13—C18	1.396 (3)
C2—H2A	0.9500	C13—C14	1.396 (3)
C3—C4	1.394 (4)	C14—C15	1.384 (3)
C3—H3A	0.9500	C15—C16	1.382 (3)
C4—C5	1.349 (4)	C15—H15A	0.9500
C4—H4A	0.9500	C16—C17	1.388 (3)
C5—C6	1.415 (4)	C16—H16A	0.9500
C5—H5A	0.9500	C17—C18	1.386 (3)
C6—C7	1.412 (4)	C17—H17A	0.9500
C7—C8	1.370 (4)	C18—H18A	0.9500
C7—H7A	0.9500
C12—N1—C13	123.4 (2)	C9—C10—C1	119.4 (2)
C12—N1—H1N1	121.0 (16)	C9—C10—C11	121.0 (2)
C13—N1—H1N1	115.6 (16)	C1—C10—C11	119.6 (2)
C10—C1—C2	123.1 (2)	C10—C11—C12	112.3 (2)
C10—C1—C6	118.9 (2)	C10—C11—H11A	109.1
C2—C1—C6	118.0 (2)	C12—C11—H11A	109.1
C3—C2—C1	121.3 (3)	C10—C11—H11B	109.1
C3—C2—H2A	119.3	C12—C11—H11B	109.1
C1—C2—H2A	119.3	H11A—C11—H11B	107.9
C2—C3—C4	119.9 (3)	O1—C12—N1	122.4 (2)
C2—C3—H3A	120.1	O1—C12—C11	121.7 (2)
C4—C3—H3A	120.1	N1—C12—C11	115.8 (2)
C5—C4—C3	121.0 (3)	C18—C13—C14	118.3 (2)
C5—C4—H4A	119.5	C18—C13—N1	120.8 (2)
C3—C4—H4A	119.5	C14—C13—N1	120.9 (2)
C4—C5—C6	121.5 (3)	C15—C14—C13	121.2 (2)
C4—C5—H5A	119.3	C15—C14—Br1	119.14 (17)
C6—C5—H5A	119.3	C13—C14—Br1	119.61 (16)
C7—C6—C5	122.1 (2)	C16—C15—C14	119.7 (2)
C7—C6—C1	119.7 (2)	C16—C15—H15A	120.2
C5—C6—C1	118.2 (2)	C14—C15—H15A	120.2
C8—C7—C6	120.1 (3)	C15—C16—C17	120.1 (2)
C8—C7—H7A	119.9	C15—C16—H16A	120.0
C6—C7—H7A	119.9	C17—C16—H16A	120.0
C7—C8—C9	119.5 (3)	C18—C17—C16	120.2 (2)
C7—C8—H8A	120.2	C18—C17—H17A	119.9
C9—C8—H8A	120.2	C16—C17—H17A	119.9
C10—C9—C8	122.3 (2)	C17—C18—C13	120.5 (2)
C10—C9—H9A	118.8	C17—C18—H18A	119.7
C8—C9—H9A	118.8	C13—C18—H18A	119.7
C10—C1—C2—C3	179.1 (3)	C6—C1—C10—C11	−177.6 (2)
C6—C1—C2—C3	−0.9 (4)	C9—C10—C11—C12	−104.1 (3)
C1—C2—C3—C4	1.4 (4)	C1—C10—C11—C12	74.6 (3)
C2—C3—C4—C5	−1.5 (5)	C13—N1—C12—O1	5.2 (4)
C3—C4—C5—C6	1.1 (5)	C13—N1—C12—C11	−172.3 (2)
C4—C5—C6—C7	−180.0 (3)	C10—C11—C12—O1	23.2 (3)
C4—C5—C6—C1	−0.6 (4)	C10—C11—C12—N1	−159.3 (2)
C10—C1—C6—C7	−0.1 (4)	C12—N1—C13—C18	−50.8 (3)
C2—C1—C6—C7	179.9 (2)	C12—N1—C13—C14	128.9 (3)
C10—C1—C6—C5	−179.5 (3)	C18—C13—C14—C15	−0.6 (3)
C2—C1—C6—C5	0.4 (4)	N1—C13—C14—C15	179.7 (2)
C5—C6—C7—C8	178.9 (3)	C18—C13—C14—Br1	178.87 (17)
C1—C6—C7—C8	−0.5 (4)	N1—C13—C14—Br1	−0.8 (3)
C6—C7—C8—C9	0.0 (4)	C13—C14—C15—C16	1.7 (3)
C7—C8—C9—C10	1.1 (4)	Br1—C14—C15—C16	−177.77 (17)
C8—C9—C10—C1	−1.7 (4)	C14—C15—C16—C17	−1.5 (3)
C8—C9—C10—C11	177.0 (2)	C15—C16—C17—C18	0.2 (4)
C2—C1—C10—C9	−178.8 (2)	C16—C17—C18—C13	0.9 (4)
C6—C1—C10—C9	1.2 (4)	C14—C13—C18—C17	−0.7 (3)
C2—C1—C10—C11	2.5 (4)	N1—C13—C18—C17	179.0 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N1···O1i	0.86 (3)	2.03 (3)	2.855 (3)	163 (2)
C11—H11A···O1i	0.99	2.55	3.279 (3)	130

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N1⋯O1i	0.86 (3)	2.03 (3)	2.855 (3)	163 (2)
C11—H11A⋯O1i	0.99	2.55	3.279 (3)	130

Symmetry code: (i) .