organic compounds
N-(4-Chlorophenyl)-4-methoxybenzamide
aX-ray Crystallography Laboratory, Post-Graduate Department of Physics & Electronics, University of Jammu, Jammu Tawi 180 006, India, and bPost-Graduate Department of Chemistry, University of Jammu, Jammu Tawi 180 006, India
*Correspondence e-mail: rkvk.paper11@gmail.com
In the title compound, C14H12ClNO2, the mean plane through the amide group [–N—C=O–] forms dihedral angles of 27.55 (8) and 31.94 (7)° with the methoxy- and chloro-substituted benzene rings, respectively. The dihedral angle between the benzene rings is 59.24 (4)°. In the crystal, N—H⋯O and weak C—H⋯O hydrogen bonds link the molecules into chains along the a axis.
Related literature
For the biological activity of et al. (2011); El Rayes et al. (2008); Regiec et al. (2006); Kuroda et al. (2006). For related structures, see: Gowda et al. (2008); Saeed et al. (2008).
see: ChenExperimental
Crystal data
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Refinement
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Data collection: CrysAlis PRO (Oxford Diffraction, 2010); cell CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: PLATON (Spek, 2009).
Supporting information
10.1107/S1600536812041384/lh5539sup1.cif
contains datablocks I, New_Global_Publ_Block. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536812041384/lh5539Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536812041384/lh5539Isup3.cml
To a mixture of 4-chloroaniline (0.127 g, 1 mmol) and aq. sodium hydroxide solution (10%, 20 ml) in a round bottom flask (50 ml), 4-methoxybenzoyl chloride (0.170 g, 1 mmol) was added in portions during stirring at room temperature. After the complete addition of 4-methoxybenzoyl chloride, the reaction mixture was further stirred for 30 minutes and then poured into ice-cold water (25 ml). It was further stirred for 10 min. and filtered. Finally, the product was obtained after drying followed by crystallization from ethanol (0.224 g, 86%) to give X-ray quality crystals.
The H atom bonded to the N atom was located in a difference map and refined independently with an isotropic displacement parameter. Other H atoms were positioned geometrically and were treated as riding on their parent C atoms, with C—H distances of 0.93–0.96 Å and with with Uiso(H) = 1.2Ueq(C) or 1.5Ueq(methyl C).
Data collection: CrysAlis PRO (Oxford Diffraction, 2010); cell
CrysAlis PRO (Oxford Diffraction, 2010); data reduction: CrysAlis PRO (Oxford Diffraction, 2010); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: PLATON (Spek, 2009).C14H12ClNO2 | Z = 2 |
Mr = 261.70 | F(000) = 272 |
Triclinic, P1 | Dx = 1.422 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 5.4394 (2) Å | Cell parameters from 6498 reflections |
b = 7.7754 (3) Å | θ = 3.5–29.0° |
c = 14.9262 (6) Å | µ = 0.31 mm−1 |
α = 78.759 (3)° | T = 293 K |
β = 80.712 (3)° | Rectangular, white |
γ = 88.821 (3)° | 0.3 × 0.2 × 0.2 mm |
V = 611.01 (4) Å3 |
Oxford Diffraction Xcalibur Sapphire3 diffractometer | 2407 independent reflections |
Radiation source: fine-focus sealed tube | 1997 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.035 |
Detector resolution: 16.1049 pixels mm-1 | θmax = 26.0°, θmin = 3.5° |
ω scan | h = −6→6 |
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010) | k = −9→9 |
Tmin = 0.952, Tmax = 1.000 | l = −18→18 |
14438 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)] = 0.039 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.100 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0427P)2 + 0.2321P] where P = (Fo2 + 2Fc2)/3 |
2407 reflections | (Δ/σ)max < 0.001 |
168 parameters | Δρmax = 0.17 e Å−3 |
0 restraints | Δρmin = −0.32 e Å−3 |
C14H12ClNO2 | γ = 88.821 (3)° |
Mr = 261.70 | V = 611.01 (4) Å3 |
Triclinic, P1 | Z = 2 |
a = 5.4394 (2) Å | Mo Kα radiation |
b = 7.7754 (3) Å | µ = 0.31 mm−1 |
c = 14.9262 (6) Å | T = 293 K |
α = 78.759 (3)° | 0.3 × 0.2 × 0.2 mm |
β = 80.712 (3)° |
Oxford Diffraction Xcalibur Sapphire3 diffractometer | 2407 independent reflections |
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010) | 1997 reflections with I > 2σ(I) |
Tmin = 0.952, Tmax = 1.000 | Rint = 0.035 |
14438 measured reflections |
R[F2 > 2σ(F2)] = 0.039 | 0 restraints |
wR(F2) = 0.100 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.03 | Δρmax = 0.17 e Å−3 |
2407 reflections | Δρmin = −0.32 e Å−3 |
168 parameters |
Experimental. CrysAlis PRO, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27–08-2010 CrysAlis171. NET) (compiled Aug 27 2010,11:50:40) 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. |
x | y | z | Uiso*/Ueq | ||
Cl1 | 0.17726 (10) | 0.35695 (7) | 0.41886 (3) | 0.05640 (19) | |
O1 | −0.1117 (2) | 0.74773 (19) | 0.00401 (9) | 0.0527 (4) | |
O2 | 0.3921 (2) | 1.08846 (18) | −0.40006 (8) | 0.0512 (4) | |
N1 | 0.2890 (3) | 0.73483 (19) | 0.02965 (10) | 0.0361 (3) | |
C1 | 0.3419 (3) | 1.0184 (2) | −0.30831 (11) | 0.0352 (4) | |
C2 | 0.1256 (3) | 0.9169 (2) | −0.27999 (12) | 0.0389 (4) | |
H2 | 0.0280 | 0.9000 | −0.3234 | 0.047* | |
C3 | 0.0551 (3) | 0.8416 (2) | −0.18864 (12) | 0.0364 (4) | |
H3 | −0.0911 | 0.7753 | −0.1706 | 0.044* | |
C4 | 0.1999 (3) | 0.8631 (2) | −0.12239 (11) | 0.0319 (4) | |
C5 | 0.4163 (3) | 0.9639 (2) | −0.15134 (11) | 0.0343 (4) | |
H5 | 0.5157 | 0.9788 | −0.1082 | 0.041* | |
C6 | 0.4869 (3) | 1.0425 (2) | −0.24313 (12) | 0.0361 (4) | |
H6 | 0.6309 | 1.1113 | −0.2611 | 0.043* | |
C7 | 0.1095 (3) | 0.7782 (2) | −0.02462 (12) | 0.0350 (4) | |
C9 | 0.2519 (3) | 0.6449 (2) | 0.12294 (11) | 0.0311 (3) | |
C10 | 0.0413 (3) | 0.6671 (2) | 0.18553 (12) | 0.0381 (4) | |
H10 | −0.0846 | 0.7411 | 0.1663 | 0.046* | |
C11 | 0.0182 (3) | 0.5794 (2) | 0.27654 (12) | 0.0391 (4) | |
H11 | −0.1230 | 0.5940 | 0.3186 | 0.047* | |
C12 | 0.2064 (3) | 0.4700 (2) | 0.30466 (12) | 0.0366 (4) | |
C13 | 0.4176 (3) | 0.4487 (2) | 0.24347 (12) | 0.0381 (4) | |
H13 | 0.5441 | 0.3758 | 0.2632 | 0.046* | |
C14 | 0.4404 (3) | 0.5361 (2) | 0.15282 (12) | 0.0362 (4) | |
H14 | 0.5830 | 0.5222 | 0.1113 | 0.043* | |
C15 | 0.6246 (4) | 1.1737 (3) | −0.43646 (14) | 0.0596 (6) | |
H15A | 0.6329 | 1.2787 | −0.4122 | 0.089* | |
H15B | 0.6418 | 1.2033 | −0.5027 | 0.089* | |
H15C | 0.7567 | 1.0970 | −0.4192 | 0.089* | |
H1 | 0.435 (4) | 0.741 (2) | 0.0024 (12) | 0.040 (5)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0657 (4) | 0.0623 (3) | 0.0364 (3) | −0.0082 (2) | −0.0090 (2) | 0.0036 (2) |
O1 | 0.0295 (7) | 0.0825 (10) | 0.0405 (7) | −0.0090 (6) | −0.0035 (5) | 0.0011 (7) |
O2 | 0.0480 (8) | 0.0676 (9) | 0.0339 (7) | −0.0103 (6) | −0.0082 (6) | 0.0022 (6) |
N1 | 0.0262 (7) | 0.0446 (8) | 0.0345 (8) | −0.0009 (6) | −0.0015 (6) | −0.0026 (6) |
C1 | 0.0342 (9) | 0.0362 (9) | 0.0347 (9) | 0.0031 (7) | −0.0061 (7) | −0.0054 (7) |
C2 | 0.0340 (9) | 0.0461 (10) | 0.0394 (9) | −0.0005 (7) | −0.0140 (7) | −0.0084 (8) |
C3 | 0.0272 (8) | 0.0396 (9) | 0.0428 (10) | −0.0034 (7) | −0.0074 (7) | −0.0068 (7) |
C4 | 0.0284 (8) | 0.0315 (8) | 0.0357 (9) | 0.0027 (6) | −0.0049 (7) | −0.0067 (6) |
C5 | 0.0306 (8) | 0.0380 (9) | 0.0359 (9) | −0.0012 (7) | −0.0096 (7) | −0.0077 (7) |
C6 | 0.0303 (8) | 0.0378 (9) | 0.0391 (9) | −0.0056 (7) | −0.0052 (7) | −0.0047 (7) |
C7 | 0.0297 (9) | 0.0390 (9) | 0.0361 (9) | −0.0016 (7) | −0.0046 (7) | −0.0070 (7) |
C9 | 0.0283 (8) | 0.0317 (8) | 0.0331 (8) | −0.0041 (6) | −0.0052 (6) | −0.0051 (6) |
C10 | 0.0299 (9) | 0.0446 (10) | 0.0400 (9) | 0.0065 (7) | −0.0066 (7) | −0.0089 (7) |
C11 | 0.0303 (8) | 0.0501 (10) | 0.0364 (9) | 0.0006 (7) | 0.0002 (7) | −0.0118 (8) |
C12 | 0.0389 (9) | 0.0373 (9) | 0.0338 (9) | −0.0088 (7) | −0.0075 (7) | −0.0047 (7) |
C13 | 0.0341 (9) | 0.0357 (9) | 0.0433 (10) | 0.0025 (7) | −0.0093 (7) | −0.0026 (7) |
C14 | 0.0271 (8) | 0.0382 (9) | 0.0413 (9) | −0.0002 (7) | −0.0006 (7) | −0.0072 (7) |
C15 | 0.0558 (13) | 0.0737 (14) | 0.0414 (11) | −0.0162 (11) | −0.0041 (9) | 0.0068 (10) |
Cl1—C12 | 1.7430 (17) | C5—H5 | 0.9300 |
O1—C7 | 1.222 (2) | C6—H6 | 0.9300 |
O2—C1 | 1.357 (2) | C9—C10 | 1.387 (2) |
O2—C15 | 1.417 (2) | C9—C14 | 1.390 (2) |
N1—C7 | 1.363 (2) | C10—C11 | 1.383 (2) |
N1—C9 | 1.416 (2) | C10—H10 | 0.9300 |
N1—H1 | 0.831 (19) | C11—C12 | 1.383 (2) |
C1—C6 | 1.388 (2) | C11—H11 | 0.9300 |
C1—C2 | 1.391 (2) | C12—C13 | 1.376 (2) |
C2—C3 | 1.370 (2) | C13—C14 | 1.378 (2) |
C2—H2 | 0.9300 | C13—H13 | 0.9300 |
C3—C4 | 1.395 (2) | C14—H14 | 0.9300 |
C3—H3 | 0.9300 | C15—H15A | 0.9600 |
C4—C5 | 1.389 (2) | C15—H15B | 0.9600 |
C4—C7 | 1.488 (2) | C15—H15C | 0.9600 |
C5—C6 | 1.383 (2) | ||
C1—O2—C15 | 118.93 (14) | C10—C9—C14 | 119.44 (15) |
C7—N1—C9 | 126.38 (14) | C10—C9—N1 | 122.65 (14) |
C7—N1—H1 | 116.3 (13) | C14—C9—N1 | 117.86 (14) |
C9—N1—H1 | 115.8 (13) | C11—C10—C9 | 120.10 (15) |
O2—C1—C6 | 125.11 (15) | C11—C10—H10 | 120.0 |
O2—C1—C2 | 115.52 (14) | C9—C10—H10 | 120.0 |
C6—C1—C2 | 119.37 (15) | C12—C11—C10 | 119.59 (16) |
C3—C2—C1 | 120.48 (15) | C12—C11—H11 | 120.2 |
C3—C2—H2 | 119.8 | C10—C11—H11 | 120.2 |
C1—C2—H2 | 119.8 | C13—C12—C11 | 120.83 (16) |
C2—C3—C4 | 120.88 (15) | C13—C12—Cl1 | 119.26 (13) |
C2—C3—H3 | 119.6 | C11—C12—Cl1 | 119.91 (14) |
C4—C3—H3 | 119.6 | C12—C13—C14 | 119.51 (15) |
C5—C4—C3 | 118.26 (15) | C12—C13—H13 | 120.2 |
C5—C4—C7 | 124.18 (14) | C14—C13—H13 | 120.2 |
C3—C4—C7 | 117.56 (14) | C13—C14—C9 | 120.52 (15) |
C6—C5—C4 | 121.25 (15) | C13—C14—H14 | 119.7 |
C6—C5—H5 | 119.4 | C9—C14—H14 | 119.7 |
C4—C5—H5 | 119.4 | O2—C15—H15A | 109.5 |
C5—C6—C1 | 119.75 (15) | O2—C15—H15B | 109.5 |
C5—C6—H6 | 120.1 | H15A—C15—H15B | 109.5 |
C1—C6—H6 | 120.1 | O2—C15—H15C | 109.5 |
O1—C7—N1 | 122.75 (16) | H15A—C15—H15C | 109.5 |
O1—C7—C4 | 121.52 (15) | H15B—C15—H15C | 109.5 |
N1—C7—C4 | 115.72 (14) | ||
C15—O2—C1—C6 | 9.0 (3) | C3—C4—C7—O1 | −26.4 (2) |
C15—O2—C1—C2 | −171.69 (17) | C5—C4—C7—N1 | −28.3 (2) |
O2—C1—C2—C3 | −179.17 (15) | C3—C4—C7—N1 | 152.68 (15) |
C6—C1—C2—C3 | 0.2 (3) | C7—N1—C9—C10 | −35.0 (3) |
C1—C2—C3—C4 | −0.8 (3) | C7—N1—C9—C14 | 147.70 (17) |
C2—C3—C4—C5 | 0.5 (2) | C14—C9—C10—C11 | −0.9 (2) |
C2—C3—C4—C7 | 179.57 (15) | N1—C9—C10—C11 | −178.21 (15) |
C3—C4—C5—C6 | 0.5 (2) | C9—C10—C11—C12 | 0.1 (3) |
C7—C4—C5—C6 | −178.52 (15) | C10—C11—C12—C13 | 0.7 (3) |
C4—C5—C6—C1 | −1.1 (3) | C10—C11—C12—Cl1 | −179.24 (13) |
O2—C1—C6—C5 | −179.93 (15) | C11—C12—C13—C14 | −0.7 (3) |
C2—C1—C6—C5 | 0.8 (2) | Cl1—C12—C13—C14 | 179.24 (13) |
C9—N1—C7—O1 | 2.7 (3) | C12—C13—C14—C9 | −0.1 (3) |
C9—N1—C7—C4 | −176.35 (15) | C10—C9—C14—C13 | 0.9 (2) |
C5—C4—C7—O1 | 152.67 (17) | N1—C9—C14—C13 | 178.35 (15) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O1i | 0.83 (4) | 2.47 (2) | 3.222 (2) | 151 (2) |
C14—H14···O1i | 0.93 | 2.56 | 3.251 (2) | 131 |
Symmetry code: (i) x+1, y, z. |
Experimental details
Crystal data | |
Chemical formula | C14H12ClNO2 |
Mr | 261.70 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 293 |
a, b, c (Å) | 5.4394 (2), 7.7754 (3), 14.9262 (6) |
α, β, γ (°) | 78.759 (3), 80.712 (3), 88.821 (3) |
V (Å3) | 611.01 (4) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.31 |
Crystal size (mm) | 0.3 × 0.2 × 0.2 |
Data collection | |
Diffractometer | Oxford Diffraction Xcalibur Sapphire3 diffractometer |
Absorption correction | Multi-scan (CrysAlis PRO; Oxford Diffraction, 2010) |
Tmin, Tmax | 0.952, 1.000 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 14438, 2407, 1997 |
Rint | 0.035 |
(sin θ/λ)max (Å−1) | 0.617 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.039, 0.100, 1.03 |
No. of reflections | 2407 |
No. of parameters | 168 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.17, −0.32 |
Computer programs: CrysAlis PRO (Oxford Diffraction, 2010), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), PLATON (Spek, 2009).
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O1i | 0.83 (4) | 2.47 (2) | 3.222 (2) | 151 (2) |
C14—H14···O1i | 0.93 | 2.56 | 3.251 (2) | 131 |
Symmetry code: (i) x+1, y, z. |
Acknowledgements
RK acknowledges the Department of Science & Technology for access to the single-crystal X-ray diffractometer sanctioned as a National Facility under project No. SR/S2/CMP-47/2003.
References
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This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
Aromatic amides have been utilized as versatile fragments to construct frameworks that have numerous functions such as molecular recognition, conformational switching, and biological activities which include in vitro xanthine oxidase (XO), tyrosinase and melanin production inhibitory activity. Further, benzanilides and their metal complexes have also been known for their marked biological activities such as antifungal,antibacterial and genotoxic effect (Chen et al., 2011). Globally, multidrug-resistant bacteria are a major health problem leading to severe consequences; anilides have shown antimycobacterial activity against classical mycobacterium tuberculosis (El Rayes et al., 2008), thiobenzanilides also belong to a group of biologically active compounds possessing antimicobacterial activities. In addition, N-substituted carboxamide isothiazoles (Regiec et al., 2006) produced a remarkable immunotropic, antiviral and anti-inflammatory activities, N-acylamino benzamides (Kuroda et al., 2006), constitute an important class of potent insecticides.
The molecular structure of the title compound (I) is shown in Fig. 1. All bond lengths and angles are normal and correspond to those observed in the related structures (Gowda et al., 2008; Saeed et al., 2008). The amide group [–N—C═O–] forms dihedral angles of 27.55 (8) and 31.94 (7)° with methoxy-substituted benzene [C1-C6] and chloro-substitued benzene [C9-C14] rings, respectively. The two benzene rings are twisted by 59.24 (4)° with respect to each other. In the crystal, N1—H1···O1i and C14—H14A···O1i hydrogen bonds link the molecules into chains along the a axis (Fig. 2) (Table 1).