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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 64| Part 7| July 2008| Page o1243
doi:10.1107/S1600536808017017

N-(3,5-Di­chloro­phen­yl)benzamide

B. Thimme Gowda,a* Sabine Foro,b B. P. Sowmyaa and Hartmut Fuessb

aDepartment of Chemistry, Mangalore University, Mangalagangotri 574 199, Mangalore, India, and bInstitute of Materials Science, Darmstadt University of Technology, Petersenstrasse 23, D-64287 Darmstadt, Germany
*Correspondence e-mail: gowdabt@yahoo.com

(Received 5 June 2008; accepted 5 June 2008; online 7 June 2008)

The conformation of the H—N—C=O unit in the title compound, C13H9Cl2NO, is trans, similar to the conformation observed in N-(3-chloro­phen­yl)benzamide, N-(2,3-dichloro­phen­yl)benzamide, N-(2,4-dichloro­phen­yl)benzamide, N-(2,6-dichloro­phen­yl)benzamide and N-(3,4-dichloro­phen­yl)benz­amide. The amide group makes dihedral angles of 14.3 (8) and 44.4 (4)° with the benzoyl and aniline rings, respectively, while the benzoyl and aniline rings form a dihedral angle of 58.3 (1)°. The mol­ecules are linked by N—H⋯O hydrogen bonds into infinite chains running along the c axis.

Related literature

For related literature, see: Gowda et al. (2003[Gowda, B. T., Jyothi, K., Paulus, H. & Fuess, H. (2003). Z. Naturforsch. Teil A, 58, 225-230.], 2007[Gowda, B. T., Sowmya, B. P., Tokarčík, M., Kožíšek, J. & Fuess, H. (2007). Acta Cryst. E63, o3365.], 2008a[Gowda, B. T., Tokarčík, M., Kožíšek, J., Sowmya, B. P. & Fuess, H. (2008a). Acta Cryst. E64, o462.],b[Gowda, B. T., Tokarčík, M., Kožíšek, J., Sowmya, B. P. & Fuess, H. (2008b). Acta Cryst. E64, o950.]).

[Scheme 1]

Experimental

Crystal data

  • C13H9Cl2NO

  • Mr = 266.11

  • Monoclinic, P 21 /c

  • a = 13.520 (1) Å

  • b = 9.9929 (8) Å

  • c = 9.4447 (7) Å

  • β = 106.357 (9)°

  • V = 1224.37 (16) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.51 mm−1

  • T = 299 (2) K

  • 0.48 × 0.36 × 0.26 mm
Data collection

  • Oxford Diffraction Xcalibur diffractometer with Sapphire CCD detector

  • Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007[Oxford Diffraction (2007). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.]) Tmin = 0.792, Tmax = 0.879

  • 7774 measured reflections

  • 2493 independent reflections

  • 1837 reflections with I > 2σ(I)

  • Rint = 0.013
Refinement

  • R[F2 > 2σ(F2)] = 0.037

  • wR(F2) = 0.133

  • S = 1.12

  • 2493 reflections

  • 181 parameters

  • Only H-atom coordinates refined

  • Δρmax = 0.44 e Å−3

  • Δρmin = −0.29 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
N1—H1N⋯O1i 0.83 (3) 2.18 (3) 2.964 (2) 157 (2)
Symmetry code: (i) [x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}].

Data collection: CrysAlis CCD (Oxford Diffraction, 2007[Oxford Diffraction (2007). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.]); cell refinement: CrysAlis RED (Oxford Diffraction, 2007[Oxford Diffraction (2007). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.]); data reduction: CrysAlis RED; 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: PLATON (Spek, 2003[Spek, A. L. (2003). J. Appl. Cryst. 36, 7-13.]); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808017017/bt2720sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808017017/bt2720Isup2.hkl

checkCIF report


Comment top

In the present work, the structure of N-(3,5-dichlorophenyl)-benzamide (N35DCPBA) has been determined to explore the effect of substituents on the solid state geometries of benzanilides (Gowda et al., 2003, 2007, 2008a, 2008b). The conformation of the H-N-C=O unit in is trans (Fig. 1), similar to that observed in N-(3-chlorophenyl)-benzamide (Gowda et al., 2008a), N-(2,3-dichlorophenyl)-benzamide and N-(3,4-dichlorophenyl)- benzamide (Gowda et al., 2007), N-(2,4-dichlorophenyl)-benzamide and N-(2,6-dichlorophenyl)-benzamide(Gowda et al., 2008b). The amide group –NHCO– makes the dihedral angles of 14.3 (8)° and 44.4 (4)° with the benzoyl and aniline rings, respectively, while the benzoyl and aniline rings form the dihedral angle of 58.3 (1)°). Part of the crystal structure of the title compound with infinite molecular chains running along the c axis is shown in Fig. 2. The chains are generated by N—H···O hydrogen bonds (Table 1)

Related literature top

For related literature, see: Gowda et al. (2003, 2007, 2008a,b).

Experimental top

The title compound was prepared according to the literature method (Gowda et al., 2003). The purity of the compound was checked by determining its melting point. It was characterized by recording its infrared and NMR spectra. Single crystals of the title compound were obtained from an ethanolic solution and used for X-ray diffraction studies at room temperature.

Refinement top

The H atoms were located in a difference map, and their positional parameters were refined freely with U(H) set to 1.2Ueq of the parent atom.

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2007); cell refinement: CrysAlis RED (Oxford Diffraction, 2007); data reduction: CrysAlis RED (Oxford Diffraction, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. Molecular structure of the title compound, showing the atom labeling scheme. The displacement ellipsoids are drawn at the 50% probability level. H atoms are represented as small spheres of arbitrary radii.
[Figure 2] Fig. 2. Molecular packing of the title compound with hydrogen bonding shown as dashed lines.
N-(3,5-Dichlorophenyl)benzamide top
Crystal data top
C13H9Cl2NOF(000) = 544
Mr = 266.11Dx = 1.444 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 3450 reflections
a = 13.520 (1) Åθ = 2.4–28.1°
b = 9.9929 (8) ŵ = 0.51 mm−1
c = 9.4447 (7) ÅT = 299 K
β = 106.357 (9)°Prism, colourless
V = 1224.37 (16) Å30.48 × 0.36 × 0.26 mm
Z = 4
Data collection top
Oxford Diffraction Xcalibur
diffractometer with Sapphire CCD detector		2493 independent reflections
Radiation source: fine-focus sealed tube1837 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.013
Rotation method data acquisition using ω and ϕ scansθmax = 26.4°, θmin = 2.6°
Absorption correction: multi-scan
(CrysAlis RED; Oxford Diffraction, 2007)		h = −12→16
Tmin = 0.792, Tmax = 0.879k = −12→12
7774 measured reflectionsl = −11→11
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)] = 0.037Hydrogen site location: difference Fourier map
wR(F2) = 0.133Only H-atom coordinates refined
S = 1.12 w = 1/[σ2(Fo2) + (0.0671P)2 + 0.5267P]
where P = (Fo2 + 2Fc2)/3
2493 reflections(Δ/σ)max = 0.010
181 parametersΔρmax = 0.44 e Å−3
0 restraintsΔρmin = −0.29 e Å−3
Crystal data top
C13H9Cl2NOV = 1224.37 (16) Å3
Mr = 266.11Z = 4
Monoclinic, P21/cMo Kα radiation
a = 13.520 (1) ŵ = 0.51 mm−1
b = 9.9929 (8) ÅT = 299 K
c = 9.4447 (7) Å0.48 × 0.36 × 0.26 mm
β = 106.357 (9)°
Data collection top
Oxford Diffraction Xcalibur
diffractometer with Sapphire CCD detector		2493 independent reflections
Absorption correction: multi-scan
(CrysAlis RED; Oxford Diffraction, 2007)		1837 reflections with I > 2σ(I)
Tmin = 0.792, Tmax = 0.879Rint = 0.013
7774 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0370 restraints
wR(F2) = 0.133Only H-atom coordinates refined
S = 1.12Δρmax = 0.44 e Å−3
2493 reflectionsΔρmin = −0.29 e Å−3
181 parameters
Special details top

Experimental. (CrysAlis RED; Oxford Diffraction, 2007) 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
C10.18869 (16)0.6454 (2)0.5651 (2)0.0370 (5)
C20.11990 (16)0.6605 (2)0.4259 (2)0.0389 (5)
H20.1002 (18)0.753 (2)0.384 (3)0.047*
C30.07367 (17)0.5473 (2)0.3519 (2)0.0412 (5)
C40.09118 (18)0.4206 (2)0.4131 (3)0.0452 (5)
H40.0558 (19)0.332 (3)0.354 (3)0.054*
C50.15740 (19)0.4104 (2)0.5533 (3)0.0446 (5)
C60.20746 (18)0.5197 (2)0.6309 (2)0.0429 (5)
H60.2544 (19)0.506 (3)0.726 (3)0.051*
C70.29164 (16)0.8484 (2)0.5806 (2)0.0357 (4)
C80.34903 (16)0.9572 (2)0.6776 (2)0.0358 (5)
C90.4140 (2)1.0369 (3)0.6232 (3)0.0525 (6)
H90.419 (2)1.022 (3)0.530 (4)0.063*
C100.4693 (2)1.1390 (3)0.7066 (3)0.0628 (7)
H100.509 (2)1.189 (3)0.663 (3)0.075*
C110.4590 (2)1.1653 (3)0.8447 (3)0.0601 (7)
H110.497 (2)1.235 (3)0.898 (3)0.072*
C120.3940 (2)1.0892 (3)0.8994 (3)0.0573 (7)
H120.379 (2)1.110 (3)0.989 (3)0.069*
C130.33965 (19)0.9850 (2)0.8168 (2)0.0450 (5)
H130.296 (2)0.942 (3)0.852 (3)0.054*
N10.24216 (15)0.75725 (18)0.64286 (19)0.0395 (4)
H1N0.2559 (19)0.753 (2)0.734 (3)0.047*
O10.29162 (14)0.84106 (17)0.45101 (16)0.0518 (4)
Cl1−0.00774 (6)0.56249 (7)0.17406 (7)0.0640 (2)
Cl20.18142 (6)0.25339 (6)0.63392 (8)0.0716 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0448 (11)0.0354 (10)0.0335 (10)−0.0010 (9)0.0157 (9)−0.0022 (8)
C20.0456 (12)0.0359 (11)0.0347 (10)0.0036 (9)0.0103 (9)0.0004 (9)
C30.0435 (12)0.0443 (12)0.0335 (10)0.0036 (9)0.0071 (9)−0.0037 (9)
C40.0516 (13)0.0381 (12)0.0453 (12)−0.0011 (10)0.0129 (10)−0.0066 (10)
C50.0552 (13)0.0331 (11)0.0468 (12)0.0031 (10)0.0163 (10)0.0038 (9)
C60.0512 (13)0.0432 (12)0.0325 (10)0.0001 (10)0.0090 (9)0.0027 (9)
C70.0421 (11)0.0355 (10)0.0295 (9)0.0026 (9)0.0103 (8)0.0006 (8)
C80.0390 (11)0.0354 (11)0.0329 (10)0.0029 (8)0.0098 (8)0.0016 (8)
C90.0641 (16)0.0570 (15)0.0413 (12)−0.0134 (12)0.0226 (11)−0.0022 (11)
C100.0679 (17)0.0681 (18)0.0550 (15)−0.0263 (14)0.0213 (13)0.0010 (13)
C110.0656 (16)0.0569 (16)0.0548 (15)−0.0226 (13)0.0120 (12)−0.0103 (12)
C120.0697 (17)0.0625 (16)0.0418 (13)−0.0181 (13)0.0195 (12)−0.0142 (12)
C130.0530 (13)0.0470 (13)0.0383 (11)−0.0120 (11)0.0181 (10)−0.0051 (10)
N10.0544 (11)0.0387 (10)0.0257 (8)−0.0073 (8)0.0120 (8)−0.0025 (7)
O10.0769 (11)0.0517 (10)0.0306 (8)−0.0128 (8)0.0215 (7)−0.0043 (7)
Cl10.0752 (5)0.0601 (4)0.0419 (3)0.0005 (3)−0.0076 (3)−0.0028 (3)
Cl20.0945 (6)0.0372 (3)0.0729 (5)0.0021 (3)0.0066 (4)0.0131 (3)
Geometric parameters (Å, º) top
C1—C21.389 (3)C7—C81.491 (3)
C1—C61.392 (3)C8—C131.385 (3)
C1—N11.419 (3)C8—C91.387 (3)
C2—C31.383 (3)C9—C101.375 (4)
C2—H21.01 (2)C9—H90.91 (3)
C3—C41.384 (3)C10—C111.375 (4)
C3—Cl11.736 (2)C10—H100.91 (3)
C4—C51.377 (3)C11—C121.369 (4)
C4—H41.09 (3)C11—H110.92 (3)
C5—C61.382 (3)C12—C131.381 (3)
C5—Cl21.734 (2)C12—H120.95 (3)
C6—H60.95 (3)C13—H130.87 (3)
C7—O11.226 (2)N1—H1N0.83 (3)
C7—N11.358 (3)
C2—C1—C6120.66 (19)C13—C8—C9118.3 (2)
C2—C1—N1120.79 (19)C13—C8—C7123.98 (19)
C6—C1—N1118.54 (19)C9—C8—C7117.74 (18)
C3—C2—C1118.4 (2)C10—C9—C8120.9 (2)
C3—C2—H2121.4 (14)C10—C9—H9119.7 (19)
C1—C2—H2120.0 (14)C8—C9—H9119.5 (19)
C2—C3—C4122.5 (2)C11—C10—C9120.1 (2)
C2—C3—Cl1119.37 (17)C11—C10—H10123 (2)
C4—C3—Cl1118.13 (17)C9—C10—H10116 (2)
C5—C4—C3117.3 (2)C12—C11—C10120.0 (2)
C5—C4—H4120.5 (14)C12—C11—H11121.7 (19)
C3—C4—H4122.3 (14)C10—C11—H11118 (2)
C4—C5—C6122.7 (2)C11—C12—C13120.1 (2)
C4—C5—Cl2118.68 (18)C11—C12—H12122.4 (19)
C6—C5—Cl2118.63 (18)C13—C12—H12117.3 (19)
C5—C6—C1118.4 (2)C12—C13—C8120.7 (2)
C5—C6—H6118.9 (17)C12—C13—H13118.0 (18)
C1—C6—H6122.7 (17)C8—C13—H13121.0 (18)
O1—C7—N1122.05 (19)C7—N1—C1123.09 (16)
O1—C7—C8120.68 (18)C7—N1—H1N119.4 (17)
N1—C7—C8117.25 (17)C1—N1—H1N115.4 (17)
C6—C1—C2—C3−2.5 (3)O1—C7—C8—C9−9.3 (3)
N1—C1—C2—C3176.84 (19)N1—C7—C8—C9169.2 (2)
C1—C2—C3—C41.9 (3)C13—C8—C9—C101.3 (4)
C1—C2—C3—Cl1−176.86 (16)C7—C8—C9—C10180.0 (2)
C2—C3—C4—C50.1 (3)C8—C9—C10—C11−1.4 (4)
Cl1—C3—C4—C5178.90 (17)C9—C10—C11—C120.2 (5)
C3—C4—C5—C6−1.6 (4)C10—C11—C12—C130.8 (5)
C3—C4—C5—Cl2−179.98 (17)C11—C12—C13—C8−0.8 (4)
C4—C5—C6—C11.0 (3)C9—C8—C13—C12−0.2 (4)
Cl2—C5—C6—C1179.39 (17)C7—C8—C13—C12−178.8 (2)
C2—C1—C6—C51.1 (3)O1—C7—N1—C11.4 (3)
N1—C1—C6—C5−178.3 (2)C8—C7—N1—C1−177.06 (19)
O1—C7—C8—C13169.3 (2)C2—C1—N1—C7−47.9 (3)
N1—C7—C8—C13−12.2 (3)C6—C1—N1—C7131.4 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1N···O1i0.83 (3)2.18 (3)2.964 (2)157 (2)
Symmetry code: (i) x, −y+3/2, z+1/2.

Experimental details

Crystal data
Chemical formulaC13H9Cl2NO
Mr266.11
Crystal system, space groupMonoclinic, P21/c
Temperature (K)299
a, b, c (Å)13.520 (1), 9.9929 (8), 9.4447 (7)
β (°) 106.357 (9)
V (Å3)1224.37 (16)
Z4
Radiation typeMo Kα
µ (mm−1)0.51
Crystal size (mm)0.48 × 0.36 × 0.26
Data collection
DiffractometerOxford Diffraction Xcalibur
diffractometer with Sapphire CCD detector
Absorption correctionMulti-scan
(CrysAlis RED; Oxford Diffraction, 2007)
Tmin, Tmax0.792, 0.879
No. of measured, independent and
observed [I > 2σ(I)] reflections		7774, 2493, 1837
Rint0.013
(sin θ/λ)max (Å−1)0.625
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.037, 0.133, 1.12
No. of reflections2493
No. of parameters181
H-atom treatmentOnly H-atom coordinates refined
Δρmax, Δρmin (e Å−3)0.44, −0.29

Computer programs: CrysAlis CCD (Oxford Diffraction, 2007), CrysAlis RED (Oxford Diffraction, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1N···O1i0.83 (3)2.18 (3)2.964 (2)157 (2)
Symmetry code: (i) x, −y+3/2, z+1/2.
 

Acknowledgements

BTG thanks the Alexander von Humboldt Foundation, Bonn, Germany, for extensions of his research fellowship.

References

First citationGowda, B. T., Jyothi, K., Paulus, H. & Fuess, H. (2003). Z. Naturforsch. Teil A, 58, 225–230.  CAS Google Scholar
 First citationGowda, B. T., Sowmya, B. P., Tokarčík, M., Kožíšek, J. & Fuess, H. (2007). Acta Cryst. E63, o3365.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationGowda, B. T., Tokarčík, M., Kožíšek, J., Sowmya, B. P. & Fuess, H. (2008a). Acta Cryst. E64, o462.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationGowda, B. T., Tokarčík, M., Kožíšek, J., Sowmya, B. P. & Fuess, H. (2008b). Acta Cryst. E64, o950.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationOxford Diffraction (2007). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.  Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationSpek, A. L. (2003). J. Appl. Cryst. 36, 7–13.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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Journal logoCRYSTALLOGRAPHIC
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ISSN: 2056-9890
Volume 64| Part 7| July 2008| Page o1243
doi:10.1107/S1600536808017017
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