2,6-Dichloro-N-(4-methyl­phen­yl)benzamide

Wei, P.-F.; Hao, L.-Y.; Yang, X.-L.; Ye, Y.-F.; Feng, Z.-Q.

doi:10.1107/S1600536812015188

organic compounds

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ISSN: 2056-9890

Volume 68| Part 5| May 2012| Page o1417

doi:10.1107/S1600536812015188

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2,6-Dichloro-N-(4-methylphenyl)benzamide

Peng-Fei Wei,^a ^* Ling-Yun Hao,^a Xiao-Li Yang,^a Yuan-Feng Ye ^a and Zhi-Qiang Feng ^a

^aCollege of Materials Engineering, Jinling Institute of Technology, Hongjing Road No.99 Nanjing, Nanjing 211146, People's Republic of China
^*Correspondence e-mail: hqzhou323@yahoo.cn

(Received 25 March 2012; accepted 6 April 2012; online 18 April 2012)

In the title compound, C₁₄H₁₁Cl₂NO, the two benzene rings are non-coplanar [dihedral angle = 60.9 (3)°]. In the crystal, an amide N—H⋯O hydrogen bond links the molecules into chains which extend along (001).

Related literature

For the synthesis of the title compound, see: Houlihan et al. (1981 ). For bond-length data, see: Allen et al. (1987 ).

Experimental

Crystal data

C₁₄H₁₁Cl₂NO
M_r = 280.14
Monoclinic, P 2₁ /c
a = 11.260 (2) Å
b = 12.786 (3) Å
c = 9.6700 (19) Å
β = 100.65 (3)°
V = 1368.2 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.46 mm⁻¹
T = 293 K
0.30 × 0.10 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: ψ scan (North et al., 1968 ) T_min = 0.874, T_max = 0.955
2650 measured reflections
2518 independent reflections
1514 reflections with I > 2sI)
R_int = 0.033
3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F² > 2σ(F²)] = 0.053
wR(F²) = 0.150
S = 1.01
2518 reflections
163 parameters
H-atom parameters constrained
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.26 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N—H0A⋯Oⁱ	0.86	1.98	2.839 (4)	173
Symmetry code: (i) $[x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995 ); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812015188/zs2197sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812015188/zs2197Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812015188/zs2197Isup3.cml

checkCIF report

Comment top

We report here the crystal structure of the title compound C₁₄H₁₁Cl₂NO. In this molecule (Fig. 1), the phenyl and dichlorophenyl rings are non-coplanar [dihedral angle 60.9 (3)°]. In the crystal structure an intermolecular amide N—H···O hydrogen bond (Table 1) links the molecules, giving one-dimensional chains which extend along (001) (Fig. 2).

Related literature top

For the synthesis of the title compound, see: Houlihan et al. (1981). For bond-length data, see: Allen et al. (1987).

Experimental top

A mixture of 4-methylbenzenamine (3.2 g, 0.03 mol), 2,6-dichlorobenzoyl chloride (6.3 g, 0.03 mol), and 6 ml of triethylamine in 50 ml of anhydrous tetrahydrofuran was refluxed with stirring for 8 h and then allowed to stand at room temperature. The resulting solids were filtered off and washed with water (2 x 30 mL) then dried, giving 7.2 g of product. Recrystallization from ethanol gave yellow crystals of the title compound. Crystals suitable for X-ray diffraction were obtained by slow evaporation of an ethanol solution.

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software (Enraf–Nonius, 1989); data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound showing the atom-numbering scheme, with displacement ellipsoids drawn at the 30% probability level.
	Fig. 2. A packing diagram of the title compound viewed down a, with intermolecular hydrogen bonds shown as dashed lines.

2,6-Dichloro-N-(4-methylphenyl)benzamide top

Crystal data top

C₁₄H₁₁Cl₂NO	F(000) = 576
M_r = 280.14	D_x = 1.360 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 11.260 (2) Å	θ = 9–13°
b = 12.786 (3) Å	µ = 0.46 mm⁻¹
c = 9.6700 (19) Å	T = 293 K
β = 100.65 (3)°	Block, yellow
V = 1368.2 (5) Å³	0.30 × 0.10 × 0.10 mm
Z = 4

Data collection top

Enraf–Nonius CAD-4 diffractometer	1514 reflections with I > 2s˘I)
Radiation source: fine-focus sealed tube	R_int = 0.033
Graphite monochromator	θ_max = 25.4°, θ_min = 1.8°
ω/2θ scans	h = −13→0
Absorption correction: ψ scan (North et al., 1968)	k = 0→15
T_min = 0.874, T_max = 0.955	l = −11→11
2650 measured reflections	3 standard reflections every 200 reflections
2518 independent reflections	intensity decay: 1%

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)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.150	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.070P)²] where P = (F_o² + 2F_c²)/3
2518 reflections	(Δ/σ)_max < 0.001
163 parameters	Δρ_max = 0.22 e Å⁻³
0 restraints	Δρ_min = −0.26 e Å⁻³

Crystal data top

C₁₄H₁₁Cl₂NO	V = 1368.2 (5) Å³
M_r = 280.14	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 11.260 (2) Å	µ = 0.46 mm⁻¹
b = 12.786 (3) Å	T = 293 K
c = 9.6700 (19) Å	0.30 × 0.10 × 0.10 mm
β = 100.65 (3)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	1514 reflections with I > 2s˘I)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0.033
T_min = 0.874, T_max = 0.955	3 standard reflections every 200 reflections
2650 measured reflections	intensity decay: 1%
2518 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.053	0 restraints
wR(F²) = 0.150	H-atom parameters constrained
S = 1.01	Δρ_max = 0.22 e Å⁻³
2518 reflections	Δρ_min = −0.26 e Å⁻³
163 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
N	0.2641 (2)	0.8121 (2)	0.1158 (3)	0.0404 (7)
H0A	0.2757	0.7889	0.2007	0.048*
O	0.2803 (3)	0.76570 (19)	−0.1064 (2)	0.0660 (8)
Cl1	0.14387 (9)	0.55959 (8)	0.07524 (10)	0.0635 (3)
C1	0.0707 (4)	1.2269 (3)	0.0646 (6)	0.0969 (17)
H1A	0.0283	1.2398	0.1404	0.145*
H1B	0.0162	1.2352	−0.0236	0.145*
H1C	0.1361	1.2758	0.0699	0.145*
Cl2	0.56778 (10)	0.75531 (9)	0.07081 (15)	0.0876 (4)
C2	0.1203 (3)	1.1167 (3)	0.0760 (5)	0.0601 (11)
C3	0.1026 (4)	1.0507 (3)	0.1828 (4)	0.0629 (11)
H3A	0.0596	1.0745	0.2500	0.076*
C4	0.1474 (3)	0.9499 (3)	0.1924 (4)	0.0533 (9)
H4A	0.1334	0.9065	0.2649	0.064*
C5	0.2128 (3)	0.9131 (2)	0.0952 (3)	0.0395 (8)
C6	0.2314 (3)	0.9779 (3)	−0.0124 (4)	0.0562 (10)
H6A	0.2750	0.9544	−0.0791	0.067*
C7	0.1848 (4)	1.0781 (3)	−0.0206 (4)	0.0661 (11)
H7A	0.1975	1.1210	−0.0941	0.079*
C8	0.2970 (3)	0.7476 (3)	0.0202 (3)	0.0423 (8)
C9	0.3616 (3)	0.6510 (3)	0.0813 (3)	0.0418 (8)
C10	0.3010 (3)	0.5611 (3)	0.1098 (3)	0.0445 (8)
C11	0.3614 (4)	0.4729 (3)	0.1667 (4)	0.0592 (10)
H11A	0.3192	0.4132	0.1837	0.071*
C12	0.4849 (4)	0.4751 (4)	0.1976 (5)	0.0730 (13)
H12A	0.5265	0.4165	0.2380	0.088*
C13	0.5485 (4)	0.5612 (4)	0.1707 (4)	0.0710 (12)
H13A	0.6324	0.5614	0.1921	0.085*
C14	0.4868 (3)	0.6472 (3)	0.1116 (4)	0.0550 (10)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N	0.0548 (17)	0.0427 (16)	0.0246 (13)	0.0042 (13)	0.0096 (12)	0.0009 (12)
O	0.112 (2)	0.0577 (16)	0.0291 (13)	0.0081 (15)	0.0157 (13)	−0.0012 (12)
Cl1	0.0531 (6)	0.0723 (7)	0.0669 (7)	−0.0039 (5)	0.0156 (5)	0.0100 (5)
C1	0.092 (4)	0.054 (3)	0.139 (5)	0.020 (3)	0.007 (3)	0.002 (3)
Cl2	0.0715 (8)	0.0718 (8)	0.1247 (11)	−0.0208 (6)	0.0314 (7)	−0.0195 (7)
C2	0.049 (2)	0.044 (2)	0.082 (3)	0.0040 (18)	0.000 (2)	−0.003 (2)
C3	0.062 (3)	0.060 (3)	0.072 (3)	0.008 (2)	0.027 (2)	−0.010 (2)
C4	0.060 (2)	0.054 (2)	0.050 (2)	0.0024 (19)	0.0204 (18)	−0.0009 (18)
C5	0.0430 (18)	0.0413 (19)	0.0337 (17)	−0.0001 (15)	0.0059 (14)	0.0015 (15)
C6	0.074 (3)	0.052 (2)	0.047 (2)	0.009 (2)	0.0222 (19)	0.0045 (18)
C7	0.083 (3)	0.051 (2)	0.063 (3)	0.003 (2)	0.010 (2)	0.013 (2)
C8	0.051 (2)	0.0449 (19)	0.0318 (18)	−0.0029 (16)	0.0087 (15)	0.0000 (16)
C9	0.050 (2)	0.045 (2)	0.0323 (17)	0.0039 (16)	0.0115 (15)	−0.0071 (15)
C10	0.050 (2)	0.051 (2)	0.0338 (17)	0.0035 (18)	0.0131 (15)	−0.0029 (17)
C11	0.072 (3)	0.051 (2)	0.057 (2)	0.008 (2)	0.018 (2)	0.0078 (18)
C12	0.073 (3)	0.067 (3)	0.077 (3)	0.027 (3)	0.011 (2)	0.009 (2)
C13	0.048 (2)	0.086 (3)	0.076 (3)	0.016 (2)	0.002 (2)	−0.004 (3)
C14	0.054 (2)	0.053 (2)	0.060 (2)	−0.0002 (19)	0.0143 (18)	−0.0102 (19)

Geometric parameters (Å, º) top

N—C8	1.341 (4)	C4—H4A	0.9300
N—C5	1.414 (4)	C5—C6	1.376 (4)
N—H0A	0.8600	C6—C7	1.381 (5)
O—C8	1.225 (4)	C6—H6A	0.9300
Cl1—C10	1.739 (4)	C7—H7A	0.9300
C1—C2	1.513 (5)	C8—C9	1.498 (5)
C1—H1A	0.9600	C9—C14	1.387 (5)
C1—H1B	0.9600	C9—C10	1.390 (5)
C1—H1C	0.9600	C10—C11	1.379 (5)
Cl2—C14	1.740 (4)	C11—C12	1.367 (6)
C2—C7	1.376 (5)	C11—H11A	0.9300
C2—C3	1.377 (5)	C12—C13	1.365 (6)
C3—C4	1.381 (5)	C12—H12A	0.9300
C3—H3A	0.9300	C13—C14	1.368 (5)
C4—C5	1.379 (4)	C13—H13A	0.9300

C8—N—C5	128.5 (3)	C2—C7—C6	122.4 (4)
C8—N—H0A	115.8	C2—C7—H7A	118.8
C5—N—H0A	115.8	C6—C7—H7A	118.8
C2—C1—H1A	109.5	O—C8—N	124.2 (3)
C2—C1—H1B	109.5	O—C8—C9	121.6 (3)
H1A—C1—H1B	109.5	N—C8—C9	114.2 (3)
C2—C1—H1C	109.5	C14—C9—C10	116.5 (3)
H1A—C1—H1C	109.5	C14—C9—C8	120.8 (3)
H1B—C1—H1C	109.5	C10—C9—C8	122.7 (3)
C7—C2—C3	117.2 (4)	C11—C10—C9	122.1 (3)
C7—C2—C1	121.3 (4)	C11—C10—Cl1	118.5 (3)
C3—C2—C1	121.5 (4)	C9—C10—Cl1	119.4 (3)
C2—C3—C4	121.4 (4)	C12—C11—C10	118.5 (4)
C2—C3—H3A	119.3	C12—C11—H11A	120.7
C4—C3—H3A	119.3	C10—C11—H11A	120.7
C5—C4—C3	120.5 (3)	C13—C12—C11	121.5 (4)
C5—C4—H4A	119.8	C13—C12—H12A	119.2
C3—C4—H4A	119.8	C11—C12—H12A	119.2
C6—C5—C4	119.0 (3)	C12—C13—C14	119.0 (4)
C6—C5—N	122.8 (3)	C12—C13—H13A	120.5
C4—C5—N	118.1 (3)	C14—C13—H13A	120.5
C5—C6—C7	119.5 (3)	C13—C14—C9	122.3 (4)
C5—C6—H6A	120.2	C13—C14—Cl2	119.1 (3)
C7—C6—H6A	120.2	C9—C14—Cl2	118.6 (3)

C7—C2—C3—C4	−0.2 (6)	O—C8—C9—C10	−96.5 (4)
C1—C2—C3—C4	179.6 (4)	N—C8—C9—C10	85.6 (4)
C2—C3—C4—C5	0.8 (6)	C14—C9—C10—C11	0.7 (5)
C3—C4—C5—C6	−0.8 (5)	C8—C9—C10—C11	−179.7 (3)
C3—C4—C5—N	175.4 (3)	C14—C9—C10—Cl1	179.8 (2)
C8—N—C5—C6	−26.7 (5)	C8—C9—C10—Cl1	−0.5 (4)
C8—N—C5—C4	157.2 (3)	C9—C10—C11—C12	1.0 (5)
C4—C5—C6—C7	0.2 (5)	Cl1—C10—C11—C12	−178.2 (3)
N—C5—C6—C7	−175.8 (3)	C10—C11—C12—C13	−1.4 (6)
C3—C2—C7—C6	−0.4 (6)	C11—C12—C13—C14	0.2 (7)
C1—C2—C7—C6	179.8 (4)	C12—C13—C14—C9	1.6 (6)
C5—C6—C7—C2	0.4 (6)	C12—C13—C14—Cl2	−177.5 (3)
C5—N—C8—O	−4.5 (5)	C10—C9—C14—C13	−2.0 (5)
C5—N—C8—C9	173.4 (3)	C8—C9—C14—C13	178.4 (3)
O—C8—C9—C14	83.1 (4)	C10—C9—C14—Cl2	177.1 (2)
N—C8—C9—C14	−94.8 (4)	C8—C9—C14—Cl2	−2.5 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N—H0A···Oⁱ	0.86	1.98	2.839 (4)	173

Symmetry code: (i) x, −y+3/2, z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₄H₁₁Cl₂NO
M_r	280.14
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	11.260 (2), 12.786 (3), 9.6700 (19)
β (°)	100.65 (3)
V (Å³)	1368.2 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.46
Crystal size (mm)	0.30 × 0.10 × 0.10

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.874, 0.955
No. of measured, independent and observed [I > 2s˘I)] reflections	2650, 2518, 1514
R_int	0.033
(sin θ/λ)_max (Å⁻¹)	0.603

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.053, 0.150, 1.01
No. of reflections	2518
No. of parameters	163
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.22, −0.26

Computer programs: CAD-4 Software (Enraf–Nonius, 1989), XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N—H0A···Oⁱ	0.86	1.98	2.839 (4)	173

Symmetry code: (i) x, −y+3/2, z+1/2.

Acknowledgements

The authors thank Liu Bo Nian from Nanjing University of Technology for useful discussions and the Center of Testing and Analysis, Nanjing University, for support.

References

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