N-(2,4-Dichloro­phen­yl)benzamide

Gowda, B.T.; Tokarčík, M.; Kožíšek, J.; Sowmya, B.P.; Fuess, H.

doi:10.1107/S1600536808012385

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 64| Part 6| June 2008| Page o950

doi:10.1107/S1600536808012385

Open

access

N-(2,4-Dichlorophenyl)benzamide

B. Thimme Gowda,^a ^* Miroslav Tokarčík,^b Jozef Kožíšek,^b B. P. Sowmya ^a and Hartmut Fuess ^c

^aDepartment of Chemistry, Mangalore University, Mangalagangotri 574 199, Mangalore, India, ^bFaculty of Chemical and Food Technology, Slovak Technical University, Radlinského 9, SK-812 37 Bratislava, Slovak Republic, and ^cInstitute of Materials Science, Darmstadt University of Technology, Petersenstrasse 23, D-64287 Darmstadt, Germany
^*Correspondence e-mail: gowdabt@yahoo.com

(Received 25 April 2008; accepted 28 April 2008; online 3 May 2008)

The conformations of the N—H and C=O bonds in the structure of the title compound, C₁₃H₉Cl₂NO, are anti to each other, similar to that observed in N-phenylbenzamide, N-(2-chlorophenyl)benzamide, N-(4-chlorophenyl)benzamide, N-(2,3-dichlorophenyl)benzamide, N-(2,6-dichlorophenyl)benzamide and other benzanilides. The amide –NHCO– group forms a dihedral angle of 33.0 (2)° with the benzoyl ring, while the rings are almost coplanar, making a dihedral angle of 2.6 (2)°). The molecules are linked by N—H⋯O hydrogen bonds into infinite chains running along the b axis.

Related literature

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

Experimental

Crystal data

C₁₃H₉Cl₂NO
M_r = 266.11
Monoclinic, P 2₁ /c
a = 11.7388 (6) Å
b = 4.7475 (2) Å
c = 22.8630 (11) Å
β = 106.360 (4)°
V = 1222.56 (10) Å³
Z = 4
Mo Kα radiation
μ = 0.51 mm⁻¹
T = 295 (2) K
0.33 × 0.06 × 0.03 mm

Data collection

Oxford Diffraction Xcalibur diffractometer
Absorption correction: analytical [CrysAlis RED (Oxford Diffraction, 2007 $[Oxford Diffraction (2007). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.]$ ), based on expressions derived by Clark & Reid (1995 )] T_min = 0.905, T_max = 0.987
11465 measured reflections
2311 independent reflections
1209 reflections with I > 2σ(I)
R_int = 0.060

Refinement

R[F² > 2σ(F²)] = 0.037
wR(F²) = 0.089
S = 1.06
2311 reflections
157 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.16 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1ⁱ	0.805 (16)	2.178 (19)	2.899 (2)	149 (2)
Symmetry code: (i) x, y-1, z.

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 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ) and DIAMOND (Brandenburg, 2002 ); software used to prepare material for publication: SHELXL97, PLATON (Spek, 2003 ) and WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808012385/om2232sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808012385/om2232Isup2.hkl

checkCIF report

Comment top

In the present work, the structure of N-(2,4-dichlorophenyl)-benzamide (N24DCPBA) has been determined to study the effect of substituents on the structures of benzanilides (Gowda et al., 2003, 2007a,b, 2008a,b). The conformations of the N—H and C=O bonds in the structure of N24DCPBA (Fig.1) are anti to each other, similar to that observed in N-(phenyl)-benzamide (NPBA) (Gowda et al., 2003), N-(2-chlorophenyl)-benzamide (N2CPBA), N-(4-chlorophenyl)-benzamide (N4CPBA), N-(2,3-dichlorophenyl)-benzamide(N23DCPBA), N-(2,6-dichlorophenyl)-benzamide (N26DCPBA) and other benzanilides (Gowda et al., 2007a,b, 2008a,b). The bond parameters in N24DCPBA are similar to those in NPBA, N2CPBA, N4CPBA, N23DCPBA, N26DCPBA and other benzanilides. The amide group –NHCO– forms the dihedral angle of 33.0 (2)° with the benzoyl ring, while the benzoyl and aniline rings are almost coplanar, with the dihedral angle of 2.6 (2)°). Part of the crystal structure of the title compound with infinite molecular chains running in the [010] direction is shown in Fig. 2. The chains are generated by N—H···O(i) hydrogen bonds (Table 1) [symmetry operation (i): x,y - 1,z].

Related literature top

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

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: ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2002); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2003) and WinGX (Farrugia, 1999).

Figures top

	Fig. 1. Molecular structure of the title compound showing the atom labelling scheme. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. Part of the crystal structure of the title compound with infinite molecular chains running in the [010] direction. The chains are generated by N—H···O(i) hydrogen bonds.[Symmetry operation (i): x,y - 1,z]. H atoms not involved in intermolecular bonding have been omitted.

N-(2,4-Dichlorophenyl)benzamide top

Crystal data top

C₁₃H₉Cl₂NO	F(000) = 544
M_r = 266.11	D_x = 1.446 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2675 reflections
a = 11.7388 (6) Å	θ = 3.5–29.1°
b = 4.7475 (2) Å	µ = 0.51 mm⁻¹
c = 22.8630 (11) Å	T = 295 K
β = 106.360 (4)°	Needle, colorless
V = 1222.56 (10) Å³	0.33 × 0.06 × 0.03 mm
Z = 4

Data collection top

Oxford Diffraction Xcalibur diffractometer	2311 independent reflections
Graphite monochromator	1209 reflections with I > 2σ(I)
Detector resolution: 10.434 pixels mm^-1	R_int = 0.060
ω scans with κ offsets	θ_max = 25.7°, θ_min = 5.1°
Absorption correction: analytical [CrysAlis RED (Oxford Diffraction, 2007), based on expressions derived by Clark & Reid (1995)]	h = −14→14
T_min = 0.905, T_max = 0.987	k = −5→5
11465 measured reflections	l = −27→27

Refinement top

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.089	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	[exp(3(sinθ/λ)²)]/ [σ²(F_o²) + (0.0389P)²] where P = 0.33333F_o² + 0.66667F_c²
2311 reflections	(Δ/σ)_max = 0.002
157 parameters	Δρ_max = 0.21 e Å⁻³
1 restraint	Δρ_min = −0.16 e Å⁻³

Crystal data top

C₁₃H₉Cl₂NO	V = 1222.56 (10) Å³
M_r = 266.11	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 11.7388 (6) Å	µ = 0.51 mm⁻¹
b = 4.7475 (2) Å	T = 295 K
c = 22.8630 (11) Å	0.33 × 0.06 × 0.03 mm
β = 106.360 (4)°

Data collection top

Oxford Diffraction Xcalibur diffractometer	2311 independent reflections
Absorption correction: analytical [CrysAlis RED (Oxford Diffraction, 2007), based on expressions derived by Clark & Reid (1995)]	1209 reflections with I > 2σ(I)
T_min = 0.905, T_max = 0.987	R_int = 0.060
11465 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	1 restraint
wR(F²) = 0.089	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	Δρ_max = 0.21 e Å⁻³
2311 reflections	Δρ_min = −0.16 e Å⁻³
157 parameters

Special details top

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

	x	y	z	U_iso*/U_eq
C1	1.0522 (2)	0.6218 (5)	0.12848 (10)	0.0496 (6)
C2	1.1434 (2)	0.5105 (5)	0.18272 (10)	0.0528 (6)
C3	1.2566 (3)	0.6149 (6)	0.19551 (12)	0.0702 (7)
H3	1.2743	0.7524	0.1704	0.084*
C4	1.3453 (3)	0.5182 (7)	0.24537 (14)	0.0849 (9)
H4	1.4223	0.5874	0.2533	0.102*
C5	1.3184 (4)	0.3218 (8)	0.28242 (14)	0.0893 (10)
H5	1.3774	0.2567	0.316	0.107*
C6	1.2056 (4)	0.2184 (6)	0.27103 (12)	0.0877 (10)
H6	1.1882	0.0849	0.297	0.105*
C7	1.1172 (3)	0.3122 (5)	0.22083 (11)	0.0677 (7)
H7	1.0405	0.2413	0.213	0.081*
C8	0.8686 (2)	0.4974 (4)	0.04960 (9)	0.0457 (6)
C9	0.8747 (2)	0.6864 (4)	0.00429 (10)	0.0518 (6)
H9	0.9462	0.7762	0.0064	0.062*
C10	0.7767 (2)	0.7427 (5)	−0.04370 (10)	0.0597 (7)
H10	0.7814	0.8708	−0.0737	0.072*
C11	0.6721 (2)	0.6086 (6)	−0.04695 (11)	0.0611 (7)
C12	0.6630 (2)	0.4146 (5)	−0.00389 (11)	0.0610 (7)
H12	0.5919	0.3208	−0.0071	0.073*
C13	0.7617 (2)	0.3632 (5)	0.04400 (10)	0.0510 (6)
N1	0.96721 (19)	0.4383 (4)	0.09966 (8)	0.0513 (5)
H1N	0.972 (2)	0.276 (4)	0.1100 (10)	0.062*
O1	1.05520 (15)	0.8645 (3)	0.11131 (7)	0.0687 (5)
Cl1	0.75028 (6)	0.12644 (14)	0.09989 (3)	0.0705 (2)
Cl2	0.54660 (7)	0.6883 (2)	−0.10654 (3)	0.1010 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0601 (15)	0.0357 (14)	0.0511 (13)	0.0050 (13)	0.0128 (12)	−0.0020 (11)
C2	0.0646 (18)	0.0412 (13)	0.0492 (13)	0.0076 (13)	0.0102 (12)	−0.0042 (11)
C3	0.0695 (19)	0.0686 (18)	0.0653 (17)	0.0051 (16)	0.0073 (14)	0.0003 (13)
C4	0.071 (2)	0.099 (2)	0.073 (2)	0.0125 (19)	0.0002 (17)	−0.0152 (19)
C5	0.100 (3)	0.089 (2)	0.0600 (19)	0.036 (2)	−0.0077 (18)	−0.0101 (17)
C6	0.131 (3)	0.072 (2)	0.0491 (16)	0.016 (2)	0.0083 (18)	0.0054 (14)
C7	0.093 (2)	0.0550 (17)	0.0504 (14)	0.0032 (15)	0.0121 (14)	0.0012 (12)
C8	0.0541 (16)	0.0349 (12)	0.0482 (13)	0.0057 (12)	0.0146 (11)	−0.0021 (11)
C9	0.0556 (15)	0.0437 (14)	0.0557 (14)	0.0016 (12)	0.0150 (12)	0.0043 (11)
C10	0.0700 (19)	0.0588 (15)	0.0510 (14)	0.0114 (14)	0.0184 (13)	0.0099 (12)
C11	0.0547 (17)	0.0721 (17)	0.0526 (14)	0.0143 (15)	0.0086 (12)	−0.0020 (14)
C12	0.0549 (16)	0.0659 (17)	0.0645 (16)	−0.0021 (13)	0.0205 (13)	−0.0069 (14)
C13	0.0566 (16)	0.0454 (13)	0.0541 (14)	0.0010 (13)	0.0204 (12)	−0.0024 (11)
N1	0.0636 (13)	0.0342 (11)	0.0531 (11)	0.0008 (11)	0.0117 (10)	0.0065 (9)
O1	0.0800 (12)	0.0347 (10)	0.0776 (11)	−0.0009 (9)	−0.0003 (9)	0.0063 (8)
Cl1	0.0783 (5)	0.0633 (4)	0.0772 (4)	−0.0034 (4)	0.0339 (4)	0.0109 (3)
Cl2	0.0706 (5)	0.1426 (8)	0.0752 (5)	0.0183 (5)	−0.0033 (4)	0.0119 (4)

Geometric parameters (Å, º) top

C1—O1	1.221 (2)	C8—C13	1.380 (3)
C1—N1	1.348 (3)	C8—C9	1.388 (3)
C1—C2	1.488 (3)	C8—N1	1.408 (3)
C2—C3	1.371 (3)	C9—C10	1.374 (3)
C2—C7	1.375 (3)	C9—H9	0.93
C3—C4	1.387 (4)	C10—C11	1.366 (3)
C3—H3	0.93	C10—H10	0.93
C4—C5	1.356 (4)	C11—C12	1.374 (3)
C4—H4	0.93	C11—Cl2	1.743 (2)
C5—C6	1.366 (5)	C12—C13	1.374 (3)
C5—H5	0.93	C12—H12	0.93
C6—C7	1.387 (4)	C13—Cl1	1.735 (2)
C6—H6	0.93	N1—H1N	0.805 (16)
C7—H7	0.93

O1—C1—N1	122.5 (2)	C13—C8—C9	117.8 (2)
O1—C1—C2	121.6 (2)	C13—C8—N1	120.1 (2)
N1—C1—C2	115.9 (2)	C9—C8—N1	122.2 (2)
C3—C2—C7	119.3 (2)	C10—C9—C8	120.9 (2)
C3—C2—C1	118.4 (2)	C10—C9—H9	119.5
C7—C2—C1	122.3 (2)	C8—C9—H9	119.5
C2—C3—C4	120.9 (3)	C11—C10—C9	119.4 (2)
C2—C3—H3	119.6	C11—C10—H10	120.3
C4—C3—H3	119.6	C9—C10—H10	120.3
C5—C4—C3	119.2 (3)	C10—C11—C12	121.6 (2)
C5—C4—H4	120.4	C10—C11—Cl2	119.3 (2)
C3—C4—H4	120.4	C12—C11—Cl2	119.1 (2)
C4—C5—C6	120.8 (3)	C13—C12—C11	118.1 (2)
C4—C5—H5	119.6	C13—C12—H12	120.9
C6—C5—H5	119.6	C11—C12—H12	120.9
C5—C6—C7	120.1 (3)	C12—C13—C8	122.2 (2)
C5—C6—H6	119.9	C12—C13—Cl1	118.62 (19)
C7—C6—H6	119.9	C8—C13—Cl1	119.18 (17)
C2—C7—C6	119.7 (3)	C1—N1—C8	126.45 (18)
C2—C7—H7	120.2	C1—N1—H1N	119.5 (18)
C6—C7—H7	120.2	C8—N1—H1N	114.0 (18)

O1—C1—C2—C3	−31.9 (3)	C9—C10—C11—C12	−1.2 (4)
N1—C1—C2—C3	147.8 (2)	C9—C10—C11—Cl2	178.01 (17)
O1—C1—C2—C7	146.7 (2)	C10—C11—C12—C13	1.7 (4)
N1—C1—C2—C7	−33.6 (3)	Cl2—C11—C12—C13	−177.46 (18)
C7—C2—C3—C4	1.6 (4)	C11—C12—C13—C8	−0.6 (3)
C1—C2—C3—C4	−179.8 (2)	C11—C12—C13—Cl1	178.13 (19)
C2—C3—C4—C5	−1.3 (4)	C9—C8—C13—C12	−1.0 (3)
C3—C4—C5—C6	0.2 (4)	N1—C8—C13—C12	179.8 (2)
C4—C5—C6—C7	0.5 (4)	C9—C8—C13—Cl1	−179.73 (16)
C3—C2—C7—C6	−0.8 (4)	N1—C8—C13—Cl1	1.0 (3)
C1—C2—C7—C6	−179.4 (2)	O1—C1—N1—C8	−3.9 (4)
C5—C6—C7—C2	−0.2 (4)	C2—C1—N1—C8	176.4 (2)
C13—C8—C9—C10	1.6 (3)	C13—C8—N1—C1	−145.5 (2)
N1—C8—C9—C10	−179.2 (2)	C9—C8—N1—C1	35.3 (3)
C8—C9—C10—C11	−0.5 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1ⁱ	0.81 (2)	2.18 (2)	2.899 (2)	149 (2)

Symmetry code: (i) x, y−1, z.

Experimental details

Crystal data
Chemical formula	C₁₃H₉Cl₂NO
M_r	266.11
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	295
a, b, c (Å)	11.7388 (6), 4.7475 (2), 22.8630 (11)
β (°)	106.360 (4)
V (Å³)	1222.56 (10)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.51
Crystal size (mm)	0.33 × 0.06 × 0.03

Data collection
Diffractometer	Oxford Diffraction Xcalibur diffractometer
Absorption correction	Analytical [CrysAlis RED (Oxford Diffraction, 2007), based on expressions derived by Clark & Reid (1995)]
T_min, T_max	0.905, 0.987
No. of measured, independent and observed [I > 2σ(I)] reflections	11465, 2311, 1209
R_int	0.060
(sin θ/λ)_max (Å⁻¹)	0.610

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.089, 1.06
No. of reflections	2311
No. of parameters	157
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.21, −0.16

Computer programs: CrysAlis CCD (Oxford Diffraction, 2007), CrysAlis RED (Oxford Diffraction, 2007), SHELXS97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2002), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2003) and WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1ⁱ	0.805 (16)	2.178 (19)	2.899 (2)	149 (2)

Symmetry code: (i) x, y−1, z.

Acknowledgements

MT and JK thank the Grant Agency of the Slovak Republic (grant No. VEGA 1/0817/08) and the Structural Funds, Interreg IIIA, for financial support in purchasing the diffractometer.

References

Brandenburg, K. (2002). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887–897. CrossRef CAS Web of Science IUCr Journals Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. CrossRef CAS IUCr Journals Google Scholar
Gowda, B. T., Jyothi, K., Paulus, H. & Fuess, H. (2003). Z. Naturforsch. Teil A, 58, 225–230. CAS Google Scholar
Gowda, B. T., Sowmya, B. P., Kožíšek, J., Tokarčík, M. & Fuess, H. (2007a). Acta Cryst. E63, o2906. Web of Science CSD CrossRef IUCr Journals Google Scholar
Gowda, B. T., Sowmya, B. P., Tokarčík, M., Kožíšek, J. & Fuess, H. (2007b). Acta Cryst. E63, o3326. Web of Science CSD CrossRef IUCr Journals Google Scholar
Gowda, B. T., Tokarčík, M., Kožíšek, J., Sowmya, B. P. & Fuess, H. (2008a). Acta Cryst. E64, o540. Web of Science CSD CrossRef IUCr Journals Google Scholar
Gowda, B. T., Tokarčík, M., Kožíšek, J., Sowmya, B. P. & Fuess, H. (2008b). Acta Cryst. E64, o769. Web of Science CSD CrossRef IUCr Journals Google Scholar
Oxford Diffraction (2007). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2003). J. Appl. Cryst. 36, 7–13. Web of Science CrossRef CAS IUCr Journals Google Scholar