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organic compounds
N-(2,6-Dichlorophenyl)-2-(naphthalen-1-yl)acetamide
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
In the title compound, C18H13Cl2NO, the naphthalene ring system and the benzene ring form dihedral angles of 74.73 (13) and 62.53 (16)°, respectively, with the acetamide grouping [maximum deviation = 0.005 (3) Å]. The naphthalene ring system forms a dihedral angle of 75.14 (13)° with the benzene ring. In the crystal, molecules are linked by N—H⋯O hydrogen bonds, forming C(4) chains propagating in [010]. The O atom also accepts two C—H⋯O interactions.
Related literature
For related structures, see: Fun et al. (2010, 2011a
,b
). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986
).
Experimental
Crystal data
|
Refinement
|
|
Data collection: APEX2 (Bruker, 2009); cell 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
10.1107/S1600536812014869/hb6731sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536812014869/hb6731Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536812014869/hb6731Isup3.cml
1-Naphthalene acetic acid (0.186 g, 1 mmol) and 2,6-dichloroaniline (0.162 g, 1 mmol), 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide hydrochloride (1.0 g, 0.01 mol) and were dissolved in dichloromethane (20ml). 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, which was extracted thrice with dichloromethane. Organic layer was washed with saturated NaHCO3 solution and brine solution, dried and concentrated under reduced pressure to give the title compound. Colourless needles were grown from N,N-dimethyl formamide solution by the slow evaporation method (m.p.: 463K).
Atom H1N1 was located in a difference Fourier map and refined freely with N1-H1N1 = 0.85 (4) Å. The remaining H atoms were positioned geometrically and refined using a riding model with C–H = 0.95 or 0.99 Å and Uiso(H) = 1.2 Ueq(C).
Data collection: APEX2 (Bruker, 2009); cell
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).C18H13Cl2NO | F(000) = 680 |
Mr = 330.19 | Dx = 1.454 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 3979 reflections |
a = 13.1918 (13) Å | θ = 3.2–30.0° |
b = 4.7199 (5) Å | µ = 0.43 mm−1 |
c = 24.878 (2) Å | T = 100 K |
β = 103.127 (3)° | Needle, colourless |
V = 1508.5 (3) Å3 | 0.38 × 0.13 × 0.08 mm |
Z = 4 |
Bruker SMART APEXII CCD diffractometer | 4397 independent reflections |
Radiation source: fine-focus sealed tube | 3245 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.055 |
ϕ and ω scans | θmax = 30.1°, θmin = 2.0° |
Absorption correction: multi-scan (SADABS; Bruker, 2009) | h = −18→18 |
Tmin = 0.853, Tmax = 0.968 | k = −6→6 |
13545 measured reflections | l = −35→35 |
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)] = 0.068 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.168 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.08 | w = 1/[σ2(Fo2) + (0.0606P)2 + 3.359P] where P = (Fo2 + 2Fc2)/3 |
4397 reflections | (Δ/σ)max = 0.001 |
203 parameters | Δρmax = 0.53 e Å−3 |
0 restraints | Δρmin = −0.56 e Å−3 |
C18H13Cl2NO | V = 1508.5 (3) Å3 |
Mr = 330.19 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 13.1918 (13) Å | µ = 0.43 mm−1 |
b = 4.7199 (5) Å | T = 100 K |
c = 24.878 (2) Å | 0.38 × 0.13 × 0.08 mm |
β = 103.127 (3)° |
Bruker SMART APEXII CCD diffractometer | 4397 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2009) | 3245 reflections with I > 2σ(I) |
Tmin = 0.853, Tmax = 0.968 | Rint = 0.055 |
13545 measured reflections |
R[F2 > 2σ(F2)] = 0.068 | 0 restraints |
wR(F2) = 0.168 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.08 | Δρmax = 0.53 e Å−3 |
4397 reflections | Δρmin = −0.56 e Å−3 |
203 parameters |
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 | ||
Cl1 | 0.46301 (6) | 0.58083 (17) | 1.15354 (3) | 0.02081 (18) | |
Cl2 | 0.13465 (6) | −0.0073 (2) | 1.03531 (3) | 0.0258 (2) | |
O1 | 0.36215 (16) | −0.0699 (5) | 1.02088 (9) | 0.0167 (4) | |
N1 | 0.32626 (19) | 0.3664 (5) | 1.04970 (10) | 0.0128 (5) | |
C1 | 0.3584 (2) | 0.3527 (7) | 1.15041 (12) | 0.0160 (6) | |
C2 | 0.3352 (2) | 0.2594 (8) | 1.19925 (13) | 0.0221 (7) | |
H2A | 0.3758 | 0.3204 | 1.2339 | 0.026* | |
C3 | 0.2519 (3) | 0.0759 (8) | 1.19680 (14) | 0.0247 (7) | |
H3A | 0.2357 | 0.0096 | 1.2299 | 0.030* | |
C4 | 0.1922 (3) | −0.0109 (7) | 1.14604 (14) | 0.0234 (7) | |
H4A | 0.1355 | −0.1375 | 1.1444 | 0.028* | |
C5 | 0.2158 (2) | 0.0887 (7) | 1.09772 (13) | 0.0186 (6) | |
C6 | 0.3005 (2) | 0.2685 (6) | 1.09881 (11) | 0.0136 (5) | |
C7 | 0.3562 (2) | 0.1873 (6) | 1.01372 (11) | 0.0123 (5) | |
C8 | 0.3845 (2) | 0.3240 (6) | 0.96339 (11) | 0.0125 (5) | |
H8A | 0.3733 | 0.5311 | 0.9645 | 0.015* | |
H8B | 0.4592 | 0.2910 | 0.9649 | 0.015* | |
C9 | 0.3199 (2) | 0.2055 (6) | 0.90964 (11) | 0.0128 (5) | |
C10 | 0.3612 (2) | 0.0027 (7) | 0.88140 (12) | 0.0156 (6) | |
H10A | 0.4293 | −0.0667 | 0.8965 | 0.019* | |
C11 | 0.3044 (2) | −0.1058 (7) | 0.83020 (12) | 0.0183 (6) | |
H11A | 0.3343 | −0.2474 | 0.8114 | 0.022* | |
C12 | 0.2067 (2) | −0.0057 (7) | 0.80799 (12) | 0.0177 (6) | |
H12A | 0.1691 | −0.0769 | 0.7735 | 0.021* | |
C13 | 0.1607 (2) | 0.2029 (6) | 0.83576 (12) | 0.0151 (6) | |
C14 | 0.0590 (2) | 0.3104 (7) | 0.81287 (12) | 0.0189 (6) | |
H14A | 0.0213 | 0.2416 | 0.7782 | 0.023* | |
C15 | 0.0150 (2) | 0.5103 (8) | 0.83999 (13) | 0.0213 (6) | |
H15A | −0.0527 | 0.5800 | 0.8240 | 0.026* | |
C16 | 0.0700 (2) | 0.6148 (7) | 0.89197 (13) | 0.0199 (6) | |
H16A | 0.0387 | 0.7521 | 0.9110 | 0.024* | |
C17 | 0.1686 (2) | 0.5172 (7) | 0.91479 (12) | 0.0171 (6) | |
H17A | 0.2052 | 0.5902 | 0.9494 | 0.021* | |
C18 | 0.2165 (2) | 0.3100 (6) | 0.88767 (12) | 0.0140 (5) | |
H1N1 | 0.332 (3) | 0.543 (8) | 1.0462 (14) | 0.014 (9)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0224 (3) | 0.0174 (4) | 0.0219 (4) | −0.0038 (3) | 0.0033 (3) | −0.0046 (3) |
Cl2 | 0.0198 (3) | 0.0294 (5) | 0.0285 (4) | −0.0066 (3) | 0.0058 (3) | −0.0084 (3) |
O1 | 0.0234 (10) | 0.0077 (10) | 0.0203 (10) | 0.0022 (8) | 0.0077 (8) | −0.0007 (8) |
N1 | 0.0208 (11) | 0.0034 (12) | 0.0152 (11) | 0.0017 (9) | 0.0057 (9) | 0.0020 (9) |
C1 | 0.0189 (13) | 0.0116 (14) | 0.0176 (13) | 0.0024 (11) | 0.0045 (10) | 0.0000 (11) |
C2 | 0.0277 (15) | 0.0230 (18) | 0.0161 (14) | 0.0069 (14) | 0.0062 (11) | 0.0013 (13) |
C3 | 0.0322 (16) | 0.0236 (18) | 0.0224 (15) | 0.0066 (15) | 0.0148 (13) | 0.0064 (14) |
C4 | 0.0271 (15) | 0.0159 (16) | 0.0317 (17) | 0.0004 (13) | 0.0163 (13) | 0.0055 (14) |
C5 | 0.0205 (13) | 0.0154 (15) | 0.0211 (14) | 0.0029 (12) | 0.0070 (11) | −0.0011 (12) |
C6 | 0.0196 (13) | 0.0059 (13) | 0.0170 (13) | 0.0030 (11) | 0.0077 (10) | 0.0021 (10) |
C7 | 0.0132 (11) | 0.0091 (13) | 0.0142 (12) | 0.0003 (10) | 0.0021 (9) | −0.0017 (11) |
C8 | 0.0161 (12) | 0.0068 (12) | 0.0148 (12) | −0.0002 (10) | 0.0041 (10) | −0.0002 (10) |
C9 | 0.0161 (12) | 0.0091 (13) | 0.0139 (12) | −0.0023 (11) | 0.0051 (10) | 0.0015 (11) |
C10 | 0.0182 (12) | 0.0120 (14) | 0.0172 (13) | −0.0008 (12) | 0.0052 (10) | 0.0002 (11) |
C11 | 0.0257 (14) | 0.0131 (15) | 0.0174 (13) | 0.0008 (12) | 0.0075 (11) | −0.0030 (12) |
C12 | 0.0238 (14) | 0.0140 (14) | 0.0146 (13) | −0.0025 (12) | 0.0032 (10) | −0.0021 (12) |
C13 | 0.0192 (13) | 0.0108 (14) | 0.0154 (13) | −0.0045 (11) | 0.0042 (10) | 0.0009 (11) |
C14 | 0.0200 (13) | 0.0174 (16) | 0.0175 (14) | −0.0017 (12) | 0.0004 (11) | 0.0010 (12) |
C15 | 0.0151 (12) | 0.0230 (17) | 0.0248 (15) | 0.0009 (12) | 0.0029 (11) | 0.0031 (13) |
C16 | 0.0220 (14) | 0.0157 (16) | 0.0231 (15) | 0.0017 (12) | 0.0075 (11) | −0.0010 (12) |
C17 | 0.0208 (13) | 0.0136 (14) | 0.0175 (13) | 0.0006 (12) | 0.0054 (10) | −0.0002 (12) |
C18 | 0.0164 (12) | 0.0098 (13) | 0.0164 (13) | −0.0009 (11) | 0.0053 (10) | 0.0006 (11) |
Cl1—C1 | 1.738 (3) | C9—C10 | 1.371 (4) |
Cl2—C5 | 1.734 (3) | C9—C18 | 1.436 (4) |
O1—C7 | 1.227 (4) | C10—C11 | 1.418 (4) |
N1—C7 | 1.354 (4) | C10—H10A | 0.9500 |
N1—C6 | 1.418 (4) | C11—C12 | 1.367 (4) |
N1—H1N1 | 0.85 (4) | C11—H11A | 0.9500 |
C1—C2 | 1.390 (4) | C12—C13 | 1.416 (4) |
C1—C6 | 1.394 (4) | C12—H12A | 0.9500 |
C2—C3 | 1.390 (5) | C13—C18 | 1.426 (4) |
C2—H2A | 0.9500 | C13—C14 | 1.426 (4) |
C3—C4 | 1.390 (5) | C14—C15 | 1.364 (5) |
C3—H3A | 0.9500 | C14—H14A | 0.9500 |
C4—C5 | 1.390 (4) | C15—C16 | 1.420 (4) |
C4—H4A | 0.9500 | C15—H15A | 0.9500 |
C5—C6 | 1.398 (4) | C16—C17 | 1.375 (4) |
C7—C8 | 1.528 (4) | C16—H16A | 0.9500 |
C8—C9 | 1.520 (4) | C17—C18 | 1.416 (4) |
C8—H8A | 0.9900 | C17—H17A | 0.9500 |
C8—H8B | 0.9900 | ||
C7—N1—C6 | 122.0 (3) | C10—C9—C18 | 119.9 (3) |
C7—N1—H1N1 | 120 (2) | C10—C9—C8 | 119.9 (3) |
C6—N1—H1N1 | 117 (2) | C18—C9—C8 | 120.2 (2) |
C2—C1—C6 | 122.1 (3) | C9—C10—C11 | 121.5 (3) |
C2—C1—Cl1 | 119.1 (2) | C9—C10—H10A | 119.3 |
C6—C1—Cl1 | 118.8 (2) | C11—C10—H10A | 119.3 |
C3—C2—C1 | 119.2 (3) | C12—C11—C10 | 119.7 (3) |
C3—C2—H2A | 120.4 | C12—C11—H11A | 120.2 |
C1—C2—H2A | 120.4 | C10—C11—H11A | 120.2 |
C4—C3—C2 | 120.2 (3) | C11—C12—C13 | 120.8 (3) |
C4—C3—H3A | 119.9 | C11—C12—H12A | 119.6 |
C2—C3—H3A | 119.9 | C13—C12—H12A | 119.6 |
C3—C4—C5 | 119.6 (3) | C12—C13—C18 | 119.9 (3) |
C3—C4—H4A | 120.2 | C12—C13—C14 | 121.4 (3) |
C5—C4—H4A | 120.2 | C18—C13—C14 | 118.7 (3) |
C4—C5—C6 | 121.6 (3) | C15—C14—C13 | 121.1 (3) |
C4—C5—Cl2 | 118.1 (3) | C15—C14—H14A | 119.5 |
C6—C5—Cl2 | 120.3 (2) | C13—C14—H14A | 119.5 |
C1—C6—C5 | 117.3 (3) | C14—C15—C16 | 120.3 (3) |
C1—C6—N1 | 120.8 (3) | C14—C15—H15A | 119.9 |
C5—C6—N1 | 121.9 (3) | C16—C15—H15A | 119.9 |
O1—C7—N1 | 122.7 (3) | C17—C16—C15 | 120.0 (3) |
O1—C7—C8 | 121.2 (3) | C17—C16—H16A | 120.0 |
N1—C7—C8 | 116.1 (3) | C15—C16—H16A | 120.0 |
C9—C8—C7 | 111.9 (2) | C16—C17—C18 | 121.1 (3) |
C9—C8—H8A | 109.2 | C16—C17—H17A | 119.4 |
C7—C8—H8A | 109.2 | C18—C17—H17A | 119.4 |
C9—C8—H8B | 109.2 | C17—C18—C13 | 118.8 (3) |
C7—C8—H8B | 109.2 | C17—C18—C9 | 122.9 (3) |
H8A—C8—H8B | 107.9 | C13—C18—C9 | 118.2 (3) |
C6—C1—C2—C3 | 0.1 (5) | C18—C9—C10—C11 | 0.7 (4) |
Cl1—C1—C2—C3 | −179.7 (3) | C8—C9—C10—C11 | −177.9 (3) |
C1—C2—C3—C4 | −0.5 (5) | C9—C10—C11—C12 | 0.5 (5) |
C2—C3—C4—C5 | −0.5 (5) | C10—C11—C12—C13 | −0.8 (5) |
C3—C4—C5—C6 | 1.9 (5) | C11—C12—C13—C18 | −0.2 (5) |
C3—C4—C5—Cl2 | −176.1 (3) | C11—C12—C13—C14 | 179.6 (3) |
C2—C1—C6—C5 | 1.2 (4) | C12—C13—C14—C15 | 179.7 (3) |
Cl1—C1—C6—C5 | −178.9 (2) | C18—C13—C14—C15 | −0.5 (5) |
C2—C1—C6—N1 | −179.8 (3) | C13—C14—C15—C16 | −0.2 (5) |
Cl1—C1—C6—N1 | 0.1 (4) | C14—C15—C16—C17 | 0.9 (5) |
C4—C5—C6—C1 | −2.3 (4) | C15—C16—C17—C18 | −0.8 (5) |
Cl2—C5—C6—C1 | 175.8 (2) | C16—C17—C18—C13 | 0.1 (5) |
C4—C5—C6—N1 | 178.7 (3) | C16—C17—C18—C9 | 179.0 (3) |
Cl2—C5—C6—N1 | −3.2 (4) | C12—C13—C18—C17 | −179.6 (3) |
C7—N1—C6—C1 | 117.3 (3) | C14—C13—C18—C17 | 0.5 (4) |
C7—N1—C6—C5 | −63.7 (4) | C12—C13—C18—C9 | 1.4 (4) |
C6—N1—C7—O1 | 0.6 (4) | C14—C13—C18—C9 | −178.4 (3) |
C6—N1—C7—C8 | −178.3 (2) | C10—C9—C18—C17 | 179.4 (3) |
O1—C7—C8—C9 | 57.7 (3) | C8—C9—C18—C17 | −2.0 (4) |
N1—C7—C8—C9 | −123.3 (3) | C10—C9—C18—C13 | −1.7 (4) |
C7—C8—C9—C10 | −99.9 (3) | C8—C9—C18—C13 | 176.9 (3) |
C7—C8—C9—C18 | 81.5 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N1···O1i | 0.84 (4) | 2.00 (4) | 2.823 (3) | 165 (3) |
C8—H8A···O1i | 0.99 | 2.37 | 3.242 (4) | 146 |
C8—H8B···O1ii | 0.99 | 2.53 | 3.488 (4) | 163 |
Symmetry codes: (i) x, y+1, z; (ii) −x+1, −y, −z+2. |
Experimental details
Crystal data | |
Chemical formula | C18H13Cl2NO |
Mr | 330.19 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 100 |
a, b, c (Å) | 13.1918 (13), 4.7199 (5), 24.878 (2) |
β (°) | 103.127 (3) |
V (Å3) | 1508.5 (3) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.43 |
Crystal size (mm) | 0.38 × 0.13 × 0.08 |
Data collection | |
Diffractometer | Bruker SMART APEXII CCD diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 2009) |
Tmin, Tmax | 0.853, 0.968 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 13545, 4397, 3245 |
Rint | 0.055 |
(sin θ/λ)max (Å−1) | 0.706 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.068, 0.168, 1.08 |
No. of reflections | 4397 |
No. of parameters | 203 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.53, −0.56 |
Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N1···O1i | 0.84 (4) | 2.00 (4) | 2.823 (3) | 165 (3) |
C8—H8A···O1i | 0.99 | 2.37 | 3.242 (4) | 146 |
C8—H8B···O1ii | 0.99 | 2.53 | 3.488 (4) | 163 |
Symmetry codes: (i) x, y+1, z; (ii) −x+1, −y, −z+2. |
Acknowledgements
The authors would like to thank Universiti Sains Malaysia for the Research University Grant (No. 1001/PFIZIK/811160). BN thanks the UGC, New Delhi, and the Government of India for the purchase of chemicals through the SAP–DRS–Phase 1 programme.
References
Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
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Fun, H.-K., Quah, C. K., Narayana, B., Nayak, P. S. & Sarojini, B. K. (2011b). Acta Cryst. E67, o2926–o2927. Web of Science CSD CrossRef IUCr Journals Google Scholar
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In continuation of our work on synthesis and structures of amides (Fun et al., 2010, 2011a,b) 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,b). The naphthalene ring system (C9-C18, maximum deviation of 0.017 (3) Å at atom C9) and the benzene ring (C1-C6) form dihedral angles of 74.73 (13) and 62.53 (16)°, respectively, with the acetamide moiety (O1/N1/C7/C8, maximum deviation of 0.005 (3) Å at atom C7). The naphthalene ring system forms a dihedral angle of 75.14 (13)° with the benzene ring.
In the crystal, Fig. 2, molecules are linked via N1–H1N1···O1, C8–H8A···O1 and C8–H8B···O1 hydrogen bonds (Table 1) into two-molecule-thick chains along [010].