PMCCPMCCPMCC

Search tips
Search criteria 

Advanced

 
Logo of actaeInternational Union of Crystallographysearchopen accessarticle submissionjournal home pagethis article
 
Acta Crystallogr Sect E Struct Rep Online. 2010 January 1; 66(Pt 1): o214.
Published online 2009 December 19. doi:  10.1107/S160053680905394X
PMCID: PMC2980066

4-Chloro-N-(2-methoxy­phen­yl)benzamide

Abstract

The title compound, C14H12ClNO2, was prepared by refluxing 4-chloro­benzoyl chloride with o-anisidine in CHCl3. The methoxy­phen­yl–amide segment of the mol­ecule is almost planar, with a dihedral angle of 5.10 (7)° between the benzene ring and the C—N—C(O)—C fragment. A weak intra­molecular N—H(...)O contact forms an S(5) ring and contributes to the planarity of this portion of the mol­ecule. The two benzene rings are inclined at an angle of 26.74 (7)°. In the crystal structure, inter­molecular Cl(...)O inter­actions of 3.1874 (9) Å generate centrosymmetric dimers. These are further linked by C—H(...)O and C—H(...)π inter­actions, forming inversion related sheets parallel to [001].

Related literature

For background to our work on benzamide derivatives, see: Saeed et al. (2008 [triangle]). For related structures, see: Balasubramanyam et al. (2003 [triangle]); Gowda et al. (2008 [triangle]); Saeed et al. (2007 [triangle]). For hydrogen-bond motifs, see: Bernstein et al. (1995 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-0o214-scheme1.jpg

Experimental

Crystal data

  • C14H12ClNO2
  • M r = 261.70
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-0o214-efi1.jpg
  • a = 7.6938 (5) Å
  • b = 9.2339 (6) Å
  • c = 9.8723 (7) Å
  • α = 66.683 (3)°
  • β = 89.943 (3)°
  • γ = 69.536 (3)°
  • V = 595.69 (7) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 0.31 mm−1
  • T = 89 K
  • 0.68 × 0.55 × 0.38 mm

Data collection

  • Bruker APEXII CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2006 [triangle]) T min = 0.762, T max = 1.000
  • 9701 measured reflections
  • 4037 independent reflections
  • 3359 reflections with I > 2σ(I)
  • R int = 0.034

Refinement

  • R[F 2 > 2σ(F 2)] = 0.039
  • wR(F 2) = 0.129
  • S = 1.11
  • 4037 reflections
  • 167 parameters
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.49 e Å−3
  • Δρmin = −0.41 e Å−3

Data collection: APEX2 (Bruker, 2006 [triangle]); cell refinement: APEX2 and SAINT (Bruker, 2006 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]) and TITAN2000 (Hunter & Simpson, 1999 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]) and TITAN2000; molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]) and Mercury (Macrae et al., 2006 [triangle]); software used to prepare material for publication: SHELXL97, enCIFer (Allen et al., 2004 [triangle]), PLATON (Spek, 2009 [triangle]) and publCIF (Westrip, 2010 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680905394X/bq2183sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680905394X/bq2183Isup2.hkl

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

Acknowledgments

We thank the University of Otago for purchase of the diffractometer.

supplementary crystallographic information

Comment

Our work on benzamide derivatives has been described in a previous paper (Saeed et al., 2008). The methoxyphenyl amide segment of the molecule is planar with a dihedral angle of 5.10 (7) ° between benzene ring and the C8—N1—C1(O1)—C2 fragment. A weak intramolecular N1—H1N···O91 contact forms an S(5) ring (Bernstein et al., 1995) and contributes to the planarity of this portion of the molecule. The O91 and C91 atoms of the methoxy group also lie close to the C8···C13 ring plane with deviations 0.0171 (17) Å for O91 and -0.040 (2)Å for C91 respectively. The two benzene rings are inclined at an angle of 26.74 (7) °. Bond distances within the molecule are similar to those observed in comparable structures (Balasubramanyam et al.,2003; Saeed et al., 2007; Gowda et al., 2008).

In the crystal structure intermolecular Cl1···O1 interactions, 3.1874 (9) Å, generate centrosymmetric dimers, Fig. 2. Molecules in these dimers are further linked by C4—H4···O1 and C6—H6···Cg interactions (Cg is the centroid of the C8···C13 ring), Table 1, forming inversion related sheets parallel to 001, Fig 3.

Experimental

A freshly prepared solution of 4-chlorobenzoyl chloride (1 mmol) in CHCl3 was treated with o-anisidine (1 mmol) under a nitrogen atmosphere at reflux for 2.5 h. Upon cooling, the reaction mixture was diluted with CHCl3 and washed consecutively with 1 M aq HCl and saturated aq NaHCO3. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. Crystallization of the residue from methanol afforded the title compound (87%) as colourless crystals: Anal. calcd. for C14H12ClNO2: C, 64.25; H, 4.62; N, 5.35%; found: C, 64.09; H, 4.71; N, 5.43%.

Refinement

The H atom on N1 was located in a difference Fourier map and refined isotropically. All other H-atoms were placed in calculated positions and refined using a riding model with d(C—H) = 0.95 Å, Uiso = 1.2Ueq (C) for aromatic and 0.98 Å, Uiso = 1.5Ueq (C) for the CH3 H atoms. The crystal was relatively weakly diffracting reducing the overall fraction of measured reflections.

Figures

Fig. 1.
The structure of (I) with displacement ellipsoids for the non-hydrogen atoms drawn at the 50% probability level. The intramolecular hydrogen bond is drawn as a dashed line.
Fig. 2.
Cl···O contacts in (I) (dashed lines) linking the molecules into centrosymmetric dimers.
Fig. 3.
Crystal packing of (I) viewed down the b axis, with hydrogen bonds drawn as dashed lines and representative C—H···π interactions shown as dotted lines. Red spheres represent the centroids of the C8···C13 ...

Crystal data

C14H12ClNO2Z = 2
Mr = 261.70F(000) = 272
Triclinic, P1Dx = 1.459 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.6938 (5) ÅCell parameters from 5193 reflections
b = 9.2339 (6) Åθ = 5.2–66.5°
c = 9.8723 (7) ŵ = 0.31 mm1
α = 66.683 (3)°T = 89 K
β = 89.943 (3)°Irregular block, colourless
γ = 69.536 (3)°0.68 × 0.55 × 0.38 mm
V = 595.69 (7) Å3

Data collection

Bruker APEXII CCD area-detector diffractometer4037 independent reflections
Radiation source: fine-focus sealed tube3359 reflections with I > 2σ(I)
graphiteRint = 0.034
ω scansθmax = 33.4°, θmin = 3.4°
Absorption correction: multi-scan (SADABS; Bruker, 2006)h = −10→11
Tmin = 0.762, Tmax = 1.000k = −14→14
9701 measured reflectionsl = −15→14

Refinement

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) = 0.129H atoms treated by a mixture of independent and constrained refinement
S = 1.11w = 1/[σ2(Fo2) + (0.0747P)2 + 0.107P] where P = (Fo2 + 2Fc2)/3
4037 reflections(Δ/σ)max = 0.001
167 parametersΔρmax = 0.49 e Å3
0 restraintsΔρmin = −0.41 e Å3

Special details

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)

xyzUiso*/Ueq
N10.96801 (14)0.46684 (13)0.22602 (12)0.01253 (19)
H1N0.884 (2)0.424 (2)0.2472 (19)0.015*
O11.05224 (13)0.67559 (12)0.23889 (11)0.01810 (19)
C10.94176 (16)0.60270 (14)0.25817 (13)0.0119 (2)
C20.76731 (16)0.65786 (14)0.32264 (13)0.0115 (2)
C30.60538 (16)0.63062 (15)0.29623 (13)0.0128 (2)
H30.60340.57370.23480.015*
C40.44720 (16)0.68559 (15)0.35862 (14)0.0137 (2)
H40.33700.66790.33960.016*
C50.45387 (16)0.76691 (15)0.44926 (13)0.0134 (2)
Cl10.25804 (4)0.83363 (4)0.53040 (3)0.01918 (10)
C60.61287 (17)0.79600 (15)0.47773 (13)0.0141 (2)
H60.61480.85140.54050.017*
C70.76861 (16)0.74244 (15)0.41260 (13)0.0129 (2)
H70.87720.76350.42940.015*
C81.12198 (15)0.38098 (14)0.17333 (13)0.0111 (2)
C91.11216 (15)0.24043 (14)0.15384 (13)0.0119 (2)
O910.95021 (12)0.21277 (11)0.18506 (10)0.01454 (18)
C910.92918 (17)0.07592 (16)0.16205 (15)0.0170 (2)
H91A0.92120.10170.05540.026*
H91B0.81420.06200.19670.026*
H91C1.0378−0.02970.21830.026*
C101.25940 (16)0.14161 (15)0.10850 (14)0.0142 (2)
H101.25140.04790.09460.017*
C111.41951 (17)0.18041 (16)0.08331 (14)0.0156 (2)
H111.52190.11150.05410.019*
C121.42992 (17)0.31922 (16)0.10069 (14)0.0156 (2)
H121.53910.34530.08260.019*
C131.28124 (16)0.42081 (15)0.14455 (14)0.0139 (2)
H131.28830.51670.15480.017*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
N10.0111 (4)0.0137 (4)0.0177 (5)−0.0062 (3)0.0069 (4)−0.0100 (4)
O10.0149 (4)0.0190 (4)0.0284 (5)−0.0099 (3)0.0084 (4)−0.0148 (4)
C10.0107 (5)0.0131 (5)0.0137 (5)−0.0044 (4)0.0027 (4)−0.0073 (4)
C20.0111 (5)0.0111 (4)0.0125 (5)−0.0037 (4)0.0023 (4)−0.0057 (4)
C30.0118 (5)0.0143 (5)0.0147 (5)−0.0051 (4)0.0034 (4)−0.0084 (4)
C40.0115 (5)0.0152 (5)0.0160 (5)−0.0054 (4)0.0037 (4)−0.0078 (4)
C50.0132 (5)0.0130 (5)0.0134 (5)−0.0035 (4)0.0047 (4)−0.0062 (4)
Cl10.01588 (16)0.02343 (17)0.02268 (17)−0.00678 (12)0.00998 (12)−0.01468 (13)
C60.0162 (5)0.0139 (5)0.0143 (5)−0.0053 (4)0.0037 (4)−0.0083 (4)
C70.0129 (5)0.0133 (5)0.0145 (5)−0.0051 (4)0.0023 (4)−0.0078 (4)
C80.0100 (4)0.0108 (4)0.0118 (5)−0.0029 (4)0.0029 (4)−0.0052 (4)
C90.0103 (5)0.0124 (5)0.0128 (5)−0.0039 (4)0.0031 (4)−0.0056 (4)
O910.0123 (4)0.0148 (4)0.0228 (5)−0.0073 (3)0.0080 (3)−0.0122 (3)
C910.0149 (5)0.0163 (5)0.0261 (6)−0.0077 (4)0.0052 (5)−0.0135 (5)
C100.0125 (5)0.0134 (5)0.0171 (5)−0.0035 (4)0.0047 (4)−0.0082 (4)
C110.0113 (5)0.0168 (5)0.0178 (6)−0.0028 (4)0.0054 (4)−0.0085 (4)
C120.0115 (5)0.0177 (5)0.0172 (5)−0.0059 (4)0.0048 (4)−0.0068 (4)
C130.0128 (5)0.0149 (5)0.0161 (5)−0.0068 (4)0.0045 (4)−0.0074 (4)

Geometric parameters (Å, °)

N1—C11.3613 (14)C7—H70.9500
N1—C81.4039 (13)C8—C131.3961 (15)
N1—H1N0.860 (17)C8—C91.4119 (15)
O1—C11.2288 (13)C9—O911.3683 (13)
C1—C21.4977 (15)C9—C101.3841 (15)
C2—C71.3977 (15)O91—C911.4301 (13)
C2—C31.3982 (15)C91—H91A0.9800
C3—C41.3901 (15)C91—H91B0.9800
C3—H30.9500C91—H91C0.9800
C4—C51.3879 (16)C10—C111.3947 (16)
C4—H40.9500C10—H100.9500
C5—C61.3920 (16)C11—C121.3873 (16)
C5—Cl11.7408 (11)C11—H110.9500
Cl1—O91i3.1874 (9)C12—C131.3951 (16)
C6—C71.3891 (15)C12—H120.9500
C6—H60.9500C13—H130.9500
C1—N1—C8128.16 (9)C13—C8—C9119.25 (10)
C1—N1—H1N115.7 (11)N1—C8—C9115.41 (9)
C8—N1—H1N116.0 (11)O91—C9—C10124.96 (10)
O1—C1—N1123.69 (10)O91—C9—C8114.45 (9)
O1—C1—C2121.14 (10)C10—C9—C8120.58 (10)
N1—C1—C2115.16 (9)C9—O91—C91117.00 (9)
C7—C2—C3119.14 (10)O91—C91—H91A109.5
C7—C2—C1117.28 (10)O91—C91—H91B109.5
C3—C2—C1123.57 (10)H91A—C91—H91B109.5
C4—C3—C2120.95 (10)O91—C91—H91C109.5
C4—C3—H3119.5H91A—C91—H91C109.5
C2—C3—H3119.5H91B—C91—H91C109.5
C5—C4—C3118.53 (10)C9—C10—C11119.63 (10)
C5—C4—H4120.7C9—C10—H10120.2
C3—C4—H4120.7C11—C10—H10120.2
C4—C5—C6121.93 (10)C12—C11—C10120.28 (10)
C4—C5—Cl1119.03 (9)C12—C11—H11119.9
C6—C5—Cl1119.04 (9)C10—C11—H11119.9
C7—C6—C5118.73 (10)C11—C12—C13120.49 (10)
C7—C6—H6120.6C11—C12—H12119.8
C5—C6—H6120.6C13—C12—H12119.8
C6—C7—C2120.71 (11)C12—C13—C8119.75 (10)
C6—C7—H7119.6C12—C13—H13120.1
C2—C7—H7119.6C8—C13—H13120.1
C13—C8—N1125.31 (10)

Symmetry codes: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C8–C13 ring.
D—H···AD—HH···AD···AD—H···A
N1—H1N···O910.855 (17)2.165 (19)2.5810 (16)109.7 (15)
C4—H4···O1ii0.952.373.3060 (15)167
C6—H6···Cg1iii0.953.333.911 (2)133

Symmetry codes: (ii) x−1, y, z; (iii) −x+2, −y+1, −z+1.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BQ2183).

References

  • Allen, F. H., Johnson, O., Shields, G. P., Smith, B. R. & Towler, M. (2004). J. Appl. Cryst.37, 335–338.
  • Balasubramanyam, K., Swaminathan, V., Ranganathan, A. & Kundu, T. K. (2003). J. Biol. Chem.278, 19134–19140. [PubMed]
  • Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl.34, 1555–1573.
  • Bruker (2006). APEX2, SAINT and SADABS Bruker AXS Inc., Madison, Wisconsin, USA.
  • Gowda, B. T., Tokarčík, M., Kožíšek, J., Sowmya, B. P. & Fuess, H. (2008). Acta Cryst. E64, o769. [PMC free article] [PubMed]
  • Hunter, K. A. & Simpson, J. (1999). TITAN2000 University of Otago, New Zealand.
  • Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst.39, 453–457.
  • Saeed, A., Hussain, S. & Bolte, M. (2007). Acta Cryst. E63, o4843.
  • Saeed, A., Khera, R. A., Abbas, N., Simpson, J. & Stanley, R. G. (2008). Acta Cryst. E64, o1976. [PMC free article] [PubMed]
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Spek, A. L. (2009). Acta Cryst. D65, 148–155. [PMC free article] [PubMed]
  • Westrip, S. P. (2010). publCIF In preparation.

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography