organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890

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

(Received 28 September 2012; accepted 2 October 2012; online 6 October 2012)

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 amides, see: Chen et al. (2011[Chen, Q., Ilies, L., Yoshikai, N. & Nakamura, E. (2011). Org. Lett. 13, 3232-3234.]); El Rayes et al. (2008[El Rayes, S. M., Ali, I. A. I. & Walid, F. (2008). Arkivoc, XI, 86-95.]); Regiec et al. (2006[Regiec, A., Machoń, Z., Miedzybrodzki, R. & Szymaniec, S. (2006). Arch. Pharm. Chem. Life Sci. 339, 401-413.]); Kuroda et al. (2006[Kuroda, N., Hird, N. & Cork, D. G. (2006). J. Comb. Chem. 8, 505-512.]). For related structures, see: Gowda et al. (2008[Gowda, B. T., Foro, S., Sowmya, B. P. & Fuess, H. (2008). Acta Cryst. E64, o1421.]); Saeed et al. (2008[Saeed, A., Khera, R. A., Gotoh, K. & Ishida, H. (2008). Acta Cryst. E64, o1934.]).

[Scheme 1]

Experimental

Crystal data
  • C14H12ClNO2

  • Mr = 261.70

  • Triclinic, [P \overline 1]

  • a = 5.4394 (2) Å

  • b = 7.7754 (3) Å

  • c = 14.9262 (6) Å

  • α = 78.759 (3)°

  • β = 80.712 (3)°

  • γ = 88.821 (3)°

  • V = 611.01 (4) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.31 mm−1

  • T = 293 K

  • 0.3 × 0.2 × 0.2 mm

Data collection
  • Oxford Diffraction Xcalibur Sapphire3 diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]) Tmin = 0.952, Tmax = 1.000

  • 14438 measured reflections

  • 2407 independent reflections

  • 1997 reflections with I > 2σ(I)

  • Rint = 0.035

Refinement
  • R[F2 > 2σ(F2)] = 0.039

  • wR(F2) = 0.100

  • S = 1.03

  • 2407 reflections

  • 168 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.17 e Å−3

  • Δρmin = −0.32 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA 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.

Data collection: CrysAlis PRO (Oxford Diffraction, 2010[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Supporting information


Comment top

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—CO–] 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).

Related literature top

For the biological activity of amides, see: Chen 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).

Experimental top

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.

Refinement top

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).

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2010); cell refinement: 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).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I) shown with 40% probability ellipsoids. H atoms are shown as small spheres of arbitrary radii.
[Figure 2] Fig. 2. The packing arrangement of molecules with dashed lines to show intermolecular N—H···O and weak C—H···O hydrogen bonds. Only H atoms involved in hydrogen bonds are shown.
N-(4-Chlorophenyl)-4-methoxybenzamide top
Crystal data top
C14H12ClNO2Z = 2
Mr = 261.70F(000) = 272
Triclinic, P1Dx = 1.422 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 5.4394 (2) ÅCell parameters from 6498 reflections
b = 7.7754 (3) Åθ = 3.5–29.0°
c = 14.9262 (6) ŵ = 0.31 mm1
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
Data collection top
Oxford Diffraction Xcalibur Sapphire3
diffractometer
2407 independent reflections
Radiation source: fine-focus sealed tube1997 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.035
Detector resolution: 16.1049 pixels mm-1θmax = 26.0°, θmin = 3.5°
ω scanh = 66
Absorption correction: multi-scan
(CrysAlis PRO; Oxford Diffraction, 2010)
k = 99
Tmin = 0.952, Tmax = 1.000l = 1818
14438 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.039Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.100H 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 parametersΔρmax = 0.17 e Å3
0 restraintsΔρmin = 0.32 e Å3
Crystal data top
C14H12ClNO2γ = 88.821 (3)°
Mr = 261.70V = 611.01 (4) Å3
Triclinic, P1Z = 2
a = 5.4394 (2) ÅMo Kα radiation
b = 7.7754 (3) ŵ = 0.31 mm1
c = 14.9262 (6) ÅT = 293 K
α = 78.759 (3)°0.3 × 0.2 × 0.2 mm
β = 80.712 (3)°
Data collection top
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 = 1.000Rint = 0.035
14438 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0390 restraints
wR(F2) = 0.100H atoms treated by a mixture of independent and constrained refinement
S = 1.03Δρmax = 0.17 e Å3
2407 reflectionsΔρmin = 0.32 e Å3
168 parameters
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cl10.17726 (10)0.35695 (7)0.41886 (3)0.05640 (19)
O10.1117 (2)0.74773 (19)0.00401 (9)0.0527 (4)
O20.3921 (2)1.08846 (18)0.40006 (8)0.0512 (4)
N10.2890 (3)0.73483 (19)0.02965 (10)0.0361 (3)
C10.3419 (3)1.0184 (2)0.30831 (11)0.0352 (4)
C20.1256 (3)0.9169 (2)0.27999 (12)0.0389 (4)
H20.02800.90000.32340.047*
C30.0551 (3)0.8416 (2)0.18864 (12)0.0364 (4)
H30.09110.77530.17060.044*
C40.1999 (3)0.8631 (2)0.12239 (11)0.0319 (4)
C50.4163 (3)0.9639 (2)0.15134 (11)0.0343 (4)
H50.51570.97880.10820.041*
C60.4869 (3)1.0425 (2)0.24313 (12)0.0361 (4)
H60.63091.11130.26110.043*
C70.1095 (3)0.7782 (2)0.02462 (12)0.0350 (4)
C90.2519 (3)0.6449 (2)0.12294 (11)0.0311 (3)
C100.0413 (3)0.6671 (2)0.18553 (12)0.0381 (4)
H100.08460.74110.16630.046*
C110.0182 (3)0.5794 (2)0.27654 (12)0.0391 (4)
H110.12300.59400.31860.047*
C120.2064 (3)0.4700 (2)0.30466 (12)0.0366 (4)
C130.4176 (3)0.4487 (2)0.24347 (12)0.0381 (4)
H130.54410.37580.26320.046*
C140.4404 (3)0.5361 (2)0.15282 (12)0.0362 (4)
H140.58300.52220.11130.043*
C150.6246 (4)1.1737 (3)0.43646 (14)0.0596 (6)
H15A0.63291.27870.41220.089*
H15B0.64181.20330.50270.089*
H15C0.75671.09700.41920.089*
H10.435 (4)0.741 (2)0.0024 (12)0.040 (5)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0657 (4)0.0623 (3)0.0364 (3)0.0082 (2)0.0090 (2)0.0036 (2)
O10.0295 (7)0.0825 (10)0.0405 (7)0.0090 (6)0.0035 (5)0.0011 (7)
O20.0480 (8)0.0676 (9)0.0339 (7)0.0103 (6)0.0082 (6)0.0022 (6)
N10.0262 (7)0.0446 (8)0.0345 (8)0.0009 (6)0.0015 (6)0.0026 (6)
C10.0342 (9)0.0362 (9)0.0347 (9)0.0031 (7)0.0061 (7)0.0054 (7)
C20.0340 (9)0.0461 (10)0.0394 (9)0.0005 (7)0.0140 (7)0.0084 (8)
C30.0272 (8)0.0396 (9)0.0428 (10)0.0034 (7)0.0074 (7)0.0068 (7)
C40.0284 (8)0.0315 (8)0.0357 (9)0.0027 (6)0.0049 (7)0.0067 (6)
C50.0306 (8)0.0380 (9)0.0359 (9)0.0012 (7)0.0096 (7)0.0077 (7)
C60.0303 (8)0.0378 (9)0.0391 (9)0.0056 (7)0.0052 (7)0.0047 (7)
C70.0297 (9)0.0390 (9)0.0361 (9)0.0016 (7)0.0046 (7)0.0070 (7)
C90.0283 (8)0.0317 (8)0.0331 (8)0.0041 (6)0.0052 (6)0.0051 (6)
C100.0299 (9)0.0446 (10)0.0400 (9)0.0065 (7)0.0066 (7)0.0089 (7)
C110.0303 (8)0.0501 (10)0.0364 (9)0.0006 (7)0.0002 (7)0.0118 (8)
C120.0389 (9)0.0373 (9)0.0338 (9)0.0088 (7)0.0075 (7)0.0047 (7)
C130.0341 (9)0.0357 (9)0.0433 (10)0.0025 (7)0.0093 (7)0.0026 (7)
C140.0271 (8)0.0382 (9)0.0413 (9)0.0002 (7)0.0006 (7)0.0072 (7)
C150.0558 (13)0.0737 (14)0.0414 (11)0.0162 (11)0.0041 (9)0.0068 (10)
Geometric parameters (Å, º) top
Cl1—C121.7430 (17)C5—H50.9300
O1—C71.222 (2)C6—H60.9300
O2—C11.357 (2)C9—C101.387 (2)
O2—C151.417 (2)C9—C141.390 (2)
N1—C71.363 (2)C10—C111.383 (2)
N1—C91.416 (2)C10—H100.9300
N1—H10.831 (19)C11—C121.383 (2)
C1—C61.388 (2)C11—H110.9300
C1—C21.391 (2)C12—C131.376 (2)
C2—C31.370 (2)C13—C141.378 (2)
C2—H20.9300C13—H130.9300
C3—C41.395 (2)C14—H140.9300
C3—H30.9300C15—H15A0.9600
C4—C51.389 (2)C15—H15B0.9600
C4—C71.488 (2)C15—H15C0.9600
C5—C61.383 (2)
C1—O2—C15118.93 (14)C10—C9—C14119.44 (15)
C7—N1—C9126.38 (14)C10—C9—N1122.65 (14)
C7—N1—H1116.3 (13)C14—C9—N1117.86 (14)
C9—N1—H1115.8 (13)C11—C10—C9120.10 (15)
O2—C1—C6125.11 (15)C11—C10—H10120.0
O2—C1—C2115.52 (14)C9—C10—H10120.0
C6—C1—C2119.37 (15)C12—C11—C10119.59 (16)
C3—C2—C1120.48 (15)C12—C11—H11120.2
C3—C2—H2119.8C10—C11—H11120.2
C1—C2—H2119.8C13—C12—C11120.83 (16)
C2—C3—C4120.88 (15)C13—C12—Cl1119.26 (13)
C2—C3—H3119.6C11—C12—Cl1119.91 (14)
C4—C3—H3119.6C12—C13—C14119.51 (15)
C5—C4—C3118.26 (15)C12—C13—H13120.2
C5—C4—C7124.18 (14)C14—C13—H13120.2
C3—C4—C7117.56 (14)C13—C14—C9120.52 (15)
C6—C5—C4121.25 (15)C13—C14—H14119.7
C6—C5—H5119.4C9—C14—H14119.7
C4—C5—H5119.4O2—C15—H15A109.5
C5—C6—C1119.75 (15)O2—C15—H15B109.5
C5—C6—H6120.1H15A—C15—H15B109.5
C1—C6—H6120.1O2—C15—H15C109.5
O1—C7—N1122.75 (16)H15A—C15—H15C109.5
O1—C7—C4121.52 (15)H15B—C15—H15C109.5
N1—C7—C4115.72 (14)
C15—O2—C1—C69.0 (3)C3—C4—C7—O126.4 (2)
C15—O2—C1—C2171.69 (17)C5—C4—C7—N128.3 (2)
O2—C1—C2—C3179.17 (15)C3—C4—C7—N1152.68 (15)
C6—C1—C2—C30.2 (3)C7—N1—C9—C1035.0 (3)
C1—C2—C3—C40.8 (3)C7—N1—C9—C14147.70 (17)
C2—C3—C4—C50.5 (2)C14—C9—C10—C110.9 (2)
C2—C3—C4—C7179.57 (15)N1—C9—C10—C11178.21 (15)
C3—C4—C5—C60.5 (2)C9—C10—C11—C120.1 (3)
C7—C4—C5—C6178.52 (15)C10—C11—C12—C130.7 (3)
C4—C5—C6—C11.1 (3)C10—C11—C12—Cl1179.24 (13)
O2—C1—C6—C5179.93 (15)C11—C12—C13—C140.7 (3)
C2—C1—C6—C50.8 (2)Cl1—C12—C13—C14179.24 (13)
C9—N1—C7—O12.7 (3)C12—C13—C14—C90.1 (3)
C9—N1—C7—C4176.35 (15)C10—C9—C14—C130.9 (2)
C5—C4—C7—O1152.67 (17)N1—C9—C14—C13178.35 (15)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O1i0.83 (4)2.47 (2)3.222 (2)151 (2)
C14—H14···O1i0.932.563.251 (2)131
Symmetry code: (i) x+1, y, z.

Experimental details

Crystal data
Chemical formulaC14H12ClNO2
Mr261.70
Crystal system, space groupTriclinic, 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)
V3)611.01 (4)
Z2
Radiation typeMo Kα
µ (mm1)0.31
Crystal size (mm)0.3 × 0.2 × 0.2
Data collection
DiffractometerOxford Diffraction Xcalibur Sapphire3
diffractometer
Absorption correctionMulti-scan
(CrysAlis PRO; Oxford Diffraction, 2010)
Tmin, Tmax0.952, 1.000
No. of measured, independent and
observed [I > 2σ(I)] reflections
14438, 2407, 1997
Rint0.035
(sin θ/λ)max1)0.617
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.039, 0.100, 1.03
No. of reflections2407
No. of parameters168
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.17, 0.32

Computer programs: CrysAlis PRO (Oxford Diffraction, 2010), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O1i0.83 (4)2.47 (2)3.222 (2)151 (2)
C14—H14···O1i0.932.563.251 (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

First citationChen, Q., Ilies, L., Yoshikai, N. & Nakamura, E. (2011). Org. Lett. 13, 3232–3234.  Web of Science CrossRef CAS PubMed
First citationEl Rayes, S. M., Ali, I. A. I. & Walid, F. (2008). Arkivoc, XI, 86–95.
First citationFarrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  CrossRef IUCr Journals
First citationGowda, B. T., Foro, S., Sowmya, B. P. & Fuess, H. (2008). Acta Cryst. E64, o1421.  Web of Science CSD CrossRef IUCr Journals
First citationKuroda, N., Hird, N. & Cork, D. G. (2006). J. Comb. Chem. 8, 505–512.  Web of Science CrossRef PubMed CAS
First citationOxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.
First citationRegiec, A., Machoń, Z., Miedzybrodzki, R. & Szymaniec, S. (2006). Arch. Pharm. Chem. Life Sci. 339, 401–413.  Web of Science CrossRef CAS
First citationSaeed, A., Khera, R. A., Gotoh, K. & Ishida, H. (2008). Acta Cryst. E64, o1934.  Web of Science CSD CrossRef IUCr Journals
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals
First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals

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