N-(2-Bromo­phen­yl)-2-(naphthalen-1-yl)acetamide

Fun, H.-K.; Quah, C.K.; Nayak, P.S.; Narayana, B.; Sarojini, B.K.

doi:10.1107/S1600536812034423

organic compounds

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ISSN: 2056-9890

Volume 68| Part 9| September 2012| Page o2657

doi:10.1107/S1600536812034423

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N-(2-Bromophenyl)-2-(naphthalen-1-yl)acetamide

Hoong-Kun Fun,^a ^*‡ Ching Kheng Quah,^a § Prakash S. Nayak,^b B. Narayana ^b and B. K. Sarojini ^c

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, ^bDepartment of Studies in Chemistry, Mangalore University, Mangalagangotri 574 199, India, and ^cDepartment of Chemistry, P.A. College of Engineering, Nadupadavu, Mangalore 574 153, India
^*Correspondence e-mail: hkfun@usm.my

(Received 31 July 2012; accepted 2 August 2012; online 8 August 2012)

In the title compound, C₁₈H₁₄BrNO, 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, molecules are linked by N—H⋯O hydrogen bonds into C(4) chains propagating in [100]. A C—H⋯O interaction reinforces the chain connectivity, generating an R₂¹(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_r = 340.21
Orthorhombic, P 2₁ 2₁ 2₁
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[F² > 2σ(F²)] = 0.029
wR(F²) = 0.061
S = 1.03
3864 reflections
195 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.63 e Å⁻³
Δρ_min = −0.33 e Å⁻³
Absolute structure: Flack (1983 ), 1587 Friedel pairs
Flack parameter: 0.001 (8)

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) x-1, y, z.

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 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812034423/hb6923sup1.cif

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

Supporting information file. DOI: 10.1107/S1600536812034423/hb6923Isup3.cml

checkCIF report

Comment top

In continuation of our work on synthesis of amides (Fun et al., 2010, 2011a, 2011b, 2012), we report herein the crystal structure of the title compound.

The molecular structure is shown in Fig. 1. Bond lengths are comparable to related structures (Fun et al., 2010, 2011a, 2011b, 2012). The naphthalene ring system (C1-C10, maximum deviation of 0.015 (3) Å at atom C9) forms a dihedral angle of 67.70 (10)° with the benzene ring (C13-C18).

In the crystal structure, Fig. 2, molecules are linked via N1–H1N1···O1 and C11–H11A···O1 hydrogen bonds (Table 1) into one-dimensional [100] chains which contain R₂¹ (6) ring motifs (Bernstein et al., 1995).

Related literature top

For general background to and related structures of the title compound, see: Fun et al. (2010, 2011a, 2011b, 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 top

1-Naphthaleneacetic acid (0.186 g, 1 mmol), 2-bromoaniline (0.1 ml, 1 mmol) and 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide hydrochloride (1.0 g, 0.01 mol) were dissolved in dichloromethane (20 ml). The mixture was stirred in presence of triethylamine at 273 K for about 3 h. The contents were poured into 100 ml of ice-cold aqueous hydrochloric acid with stirring. The concotion was then extracted thrice with dichloromethane. The organic layer was washed with saturated NaHCO₃ solution and brine solution, dried and concentrated under reduced pressure to give the title compound. Colourless blocks were grown from toluene solution by the slow evaporation method (m.p.: 421K).

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound showing 40% probability displacement ellipsoids for non-H atoms.
	Fig. 2. The crystal structure of the title compound, viewed along the c axis. H atoms not involved in hydrogen bonds (dashed lines) have been omitted for clarity.

N-(2-Bromophenyl)-2-(naphthalen-1-yl)acetamide top

Crystal data top

C₁₈H₁₄BrNO	F(000) = 688
M_r = 340.21	D_x = 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

Data collection top

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

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)] = 0.029	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.061	w = 1/[σ²(F_o²) + (0.0272P)² + 0.2223P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max = 0.001
3864 reflections	Δρ_max = 0.63 e Å⁻³
195 parameters	Δρ_min = −0.33 e Å⁻³
0 restraints	Absolute structure: Flack (1983), 1587 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.001 (8)

Crystal data top

C₁₈H₁₄BrNO	V = 1452.68 (6) Å³
M_r = 340.21	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 4.7603 (1) Å	µ = 2.83 mm⁻¹
b = 11.4614 (3) Å	T = 100 K
c = 26.6255 (6) Å	0.32 × 0.16 × 0.13 mm

Data collection top

Bruker SMART APEXII CCD diffractometer	3864 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	3516 reflections with I > 2σ(I)
T_min = 0.463, T_max = 0.719	R_int = 0.031
16642 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.029	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.061	Δρ_max = 0.63 e Å⁻³
S = 1.03	Δρ_min = −0.33 e Å⁻³
3864 reflections	Absolute structure: Flack (1983), 1587 Friedel pairs
195 parameters	Absolute structure parameter: 0.001 (8)
0 restraints

Special details top

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.

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

	x	y	z	U_iso*/U_eq
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)*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) x−1, y, z.

Experimental details

Crystal data
Chemical formula	C₁₈H₁₄BrNO
M_r	340.21
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	100
a, b, c (Å)	4.7603 (1), 11.4614 (3), 26.6255 (6)
V (Å³)	1452.68 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	2.83
Crystal size (mm)	0.32 × 0.16 × 0.13

Data collection
Diffractometer	Bruker SMART APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.463, 0.719
No. of measured, independent and observed [I > 2σ(I)] reflections	16642, 3864, 3516
R_int	0.031
(sin θ/λ)_max (Å⁻¹)	0.682

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.029, 0.061, 1.03
No. of reflections	3864
No. of parameters	195
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.63, −0.33
Absolute structure	Flack (1983), 1587 Friedel pairs
Absolute structure parameter	0.001 (8)

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

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) x−1, y, z.

Footnotes

‡Thomson Reuters ResearcherID: A-3561-2009.

§Thomson Reuters ResearcherID: A-5525-2009.

Acknowledgements

The authors thank Universiti Sains Malaysia (USM) for the Research University Grant (No. 1001/PFIZIK/811160). BN also thanks UGC, New Delhi, and the Government of India for the purchase of chemicals through the SAP-DRS-Phase 1 programme.

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