2,4-Dichloro-N-o-tolyl­benzamide

Saeed, A.; Khera, R.A.; Simpson, J.; Stanley, R.G.

doi:10.1107/S1600536809022752

organic compounds

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ISSN: 2056-9890

Volume 65| Part 7| July 2009| Page o1642

doi:10.1107/S1600536809022752

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2,4-Dichloro-N-o-tolylbenzamide

Aamer Saeed,^a ^* Rasheed Ahmad Khera,^a Jim Simpson ^b and Roderick G. Stanley ^b

^aDepartment of Chemistry, Quaid-i-Azam University, Islamabad 45320, Pakistan, and ^bDepartment of Chemistry, University of Otago, PO Box 56, Dunedin, New Zealand
^*Correspondence e-mail: aamersaeed@yahoo.com

(Received 11 June 2009; accepted 13 June 2009; online 20 June 2009)

In the title compound, C₁₄H₁₁Cl₂NO, the central C—C(O)—N—C amide unit makes dihedral angles of 68.71 (11) and 54.92 (12)°, respectively, with the dichlorobenzene and tolyl rings. The two aromatic rings are inclined at 16.25 (17)°. In the crystal, N—H⋯O hydrogen bonds link molecules into zigzag chains propagating in [001]. C—H⋯Cl contacts link these chains and additional C—H⋯O contacts generate stacks down b. Weak C—H⋯π and C—Cl⋯π interactions [Cl⋯centroid distance = 3.5422 (15) Å] may also stabilize the structure.

Related literature

For the biological activity of benzamide derivatives, see: Saeed et al. (2008a ). For related structures, see: Gowda et al. (2008 ); Saeed et al. (2008b ); Zhou & Zheng (2007 ). For reference structural data, see: Allen et al. (1987 ).

Experimental

Crystal data

C₁₄H₁₁Cl₂NO
M_r = 280.14
Monoclinic, C c
a = 22.517 (4) Å
b = 6.0405 (9) Å
c = 9.6332 (17) Å
β = 104.838 (9)°
V = 1266.6 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.50 mm⁻¹
T = 92 K
0.46 × 0.27 × 0.19 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2006 ) T_min = 0.615, T_max = 0.91
9889 measured reflections
3475 independent reflections
3195 reflections with I > 2σ(I)
R_int = 0.043

Refinement

R[F² > 2σ(F²)] = 0.057
wR(F²) = 0.158
S = 1.15
3475 reflections
164 parameters
2 restraints
H-atom parameters constrained
Δρ_max = 1.36 e Å⁻³
Δρ_min = −0.62 e Å⁻³
Absolute structure: Flack (1983 ), 1248 Friedel pairs
Flack parameter: 0.05 (8)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1ⁱ	0.88	2.04	2.865 (4)	156
C6—H6⋯O1ⁱⁱ	0.95	2.55	3.415 (4)	151
C11—H11⋯Cl2ⁱⁱⁱ	0.95	2.83	3.680 (3)	150
C14—H14C⋯Cg2ⁱ	0.98	2.87	3.528 (4)	125
Symmetry codes: (i) $[x, -y+1, z-{\script{1\over 2}}]$ ; (ii) $[x, -y+2, z-{\script{1\over 2}}]$ ; (iii) $[x-{\script{1\over 2}}, y-{\script{3\over 2}}, z]$ . Cg2 is the centroid of the C8–C13 ring.

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

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809022752/tk2478sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809022752/tk2478Isup2.hkl

checkCIF report

Comment top

The biological activity and applications of benzamide derivatives have been described in an earlier paper (Saeed et al. 2008a). In the title compound, (I) & Fig. 1, the central C2–C1(O1)–N1–C8 amide unit makes dihedral angles of 68.71 (11) ° and 54.92 (12) ° with the C2···C7 and C8···C13 rings, respectively. The two aromatic rings are inclined at 16.25 (17)°. Bond distances within the molecule are normal (Allen et al. 1987) and similar to those observed in comparable structures (Gowda et al. 2008; Saeed et al. 2008b; Zhou & Zheng 2007). In the crystal, N1—H1···O1 hydrogen bonds link molecules into zig-zag chains down the c axis; Table 1 & Fig. 2. C11—H11···Cl2 contacts link these chains and additional C6—H6···O1 contacts generate three-dimensional stacks down b, Fig. 3. C14—H14···π and Cl1···π interactions (Cl···Cg1 distance 3.5422 (15) Å; Cg1 is the centroid of the C2···C7 ring) may also stabilize the structure.

Related literature top

For the biological activity of benzamide derivatives, see: Saeed et al. (2008a). For related structures, see: Gowda et al. (2008); Saeed et al. (2008b); Zhou & Zheng (2007). For reference structural data, see: Allen et al. (1987). Cg1 is the centroid of the C2–C7 ring.

Experimental top

2,4-Dichlorobenzoyl chloride (5.4 mmol) in CHCl₃ was treated with 2-methylaniline (21.6 mmol) under a nitrogen atmosphere at reflux for 3 h. Upon cooling, the reaction mixture was diluted with CHCl₃ and washed consecutively with aq. 1 M HCl and saturated aq. NaHCO₃. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. Crystallization of the residue in CHCl₃ afforded (I) (81%) as colourless crystals: Anal. calcd. for C₁₄H₁₁Cl₂NO: C 60.02, H 3.96, N 5.00%; found: C 60.05, H 3.97, N 4.97%.

Computing details top

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

Figures top

	Fig. 1. The structure of (I) with displacement ellipsoids for the non-hydrogen atoms drawn at the 50% probability level.
	Fig. 2. Zig-zag chains of (I) down the c axis. Dashed lines indicate N—H···O hydrogen bonds and C—H···Cl contacts.
	Fig. 3. Crystal packing of (I) viewed down the b axis. Dashed lines indicate N—H···O hydrogen bonds as well as C—H···O and C—H···Cl contacts.

2,4-Dichloro-N-o-tolylbenzamide top

Crystal data top

C₁₄H₁₁Cl₂NO	F(000) = 576
M_r = 280.14	D_x = 1.469 Mg m⁻³
Monoclinic, Cc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2yc	Cell parameters from 5253 reflections
a = 22.517 (4) Å	θ = 2.2–32.4°
b = 6.0405 (9) Å	µ = 0.50 mm⁻¹
c = 9.6332 (17) Å	T = 92 K
β = 104.838 (9)°	Block, colourless
V = 1266.6 (4) Å³	0.46 × 0.27 × 0.19 mm
Z = 4

Data collection top

Bruker APEXII CCD diffractometer	3475 independent reflections
Radiation source: fine-focus sealed tube	3195 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.043
ω scans	θ_max = 33.1°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2006)	h = −34→33
T_min = 0.615, T_max = 0.91	k = −9→8
9889 measured reflections	l = −12→14

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.057	H-atom parameters constrained
wR(F²) = 0.158	w = 1/[σ²(F_o²) + (0.0952P)² + 1.0992P] where P = (F_o² + 2F_c²)/3
S = 1.15	(Δ/σ)_max < 0.001
3475 reflections	Δρ_max = 1.36 e Å⁻³
164 parameters	Δρ_min = −0.62 e Å⁻³
2 restraints	Absolute structure: Flack (1983), 1248 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.05 (8)

Crystal data top

C₁₄H₁₁Cl₂NO	V = 1266.6 (4) Å³
M_r = 280.14	Z = 4
Monoclinic, Cc	Mo Kα radiation
a = 22.517 (4) Å	µ = 0.50 mm⁻¹
b = 6.0405 (9) Å	T = 92 K
c = 9.6332 (17) Å	0.46 × 0.27 × 0.19 mm
β = 104.838 (9)°

Data collection top

Bruker APEXII CCD diffractometer	3475 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2006)	3195 reflections with I > 2σ(I)
T_min = 0.615, T_max = 0.91	R_int = 0.043
9889 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.057	H-atom parameters constrained
wR(F²) = 0.158	Δρ_max = 1.36 e Å⁻³
S = 1.15	Δρ_min = −0.62 e Å⁻³
3475 reflections	Absolute structure: Flack (1983), 1248 Friedel pairs
164 parameters	Absolute structure parameter: 0.05 (8)
2 restraints

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
O1	0.16543 (13)	0.5847 (4)	0.3277 (3)	0.0250 (5)
C1	0.17020 (14)	0.5816 (5)	0.2022 (3)	0.0185 (5)
C2	0.22063 (13)	0.7094 (5)	0.1617 (3)	0.0172 (5)
C3	0.28213 (14)	0.6506 (5)	0.2168 (3)	0.0173 (5)
Cl1	0.30103 (4)	0.41955 (12)	0.32639 (7)	0.02356 (18)
C4	0.32950 (13)	0.7736 (5)	0.1848 (3)	0.0178 (5)
H4	0.3712	0.7311	0.2212	0.021*
C5	0.31386 (14)	0.9607 (5)	0.0978 (3)	0.0184 (5)
Cl2	0.37258 (4)	1.11763 (13)	0.06163 (7)	0.02513 (18)
C6	0.25310 (15)	1.0223 (5)	0.0405 (3)	0.0211 (5)
H6	0.2433	1.1492	−0.0192	0.025*
C7	0.20711 (15)	0.8956 (5)	0.0719 (3)	0.0202 (6)
H7	0.1654	0.9355	0.0319	0.024*
N1	0.13248 (12)	0.4699 (5)	0.0939 (3)	0.0197 (5)
H1	0.1365	0.4894	0.0063	0.024*
C8	0.08611 (13)	0.3210 (5)	0.1147 (3)	0.0191 (5)
C9	0.10239 (14)	0.1560 (5)	0.2194 (3)	0.0218 (6)
H9	0.1435	0.1458	0.2762	0.026*
C10	0.05858 (17)	0.0073 (6)	0.2407 (4)	0.0272 (7)
H10	0.0696	−0.1041	0.3123	0.033*
C11	−0.00132 (17)	0.0223 (6)	0.1568 (4)	0.0291 (7)
H11	−0.0316	−0.0780	0.1719	0.035*
C12	−0.01736 (15)	0.1832 (6)	0.0507 (4)	0.0261 (6)
H12	−0.0584	0.1889	−0.0075	0.031*
C13	0.02600 (14)	0.3385 (5)	0.0276 (3)	0.0203 (5)
C14	0.00831 (15)	0.5163 (6)	−0.0857 (4)	0.0261 (6)
H14A	0.0153	0.6622	−0.0401	0.039*
H14B	−0.0352	0.5007	−0.1358	0.039*
H14C	0.0333	0.5012	−0.1548	0.039*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0322 (12)	0.0350 (13)	0.0103 (10)	−0.0082 (9)	0.0100 (9)	−0.0035 (8)
C1	0.0219 (12)	0.0242 (13)	0.0107 (12)	−0.0017 (9)	0.0067 (10)	−0.0010 (9)
C2	0.0202 (11)	0.0246 (13)	0.0082 (10)	−0.0028 (9)	0.0060 (9)	−0.0016 (9)
C3	0.0242 (12)	0.0183 (11)	0.0107 (11)	−0.0014 (9)	0.0067 (9)	−0.0010 (9)
Cl1	0.0313 (4)	0.0213 (3)	0.0185 (3)	0.0008 (2)	0.0070 (3)	0.0049 (2)
C4	0.0207 (13)	0.0207 (12)	0.0125 (12)	−0.0008 (9)	0.0048 (10)	0.0008 (9)
C5	0.0230 (12)	0.0197 (11)	0.0139 (13)	−0.0038 (9)	0.0074 (10)	−0.0004 (9)
Cl2	0.0260 (3)	0.0289 (3)	0.0217 (4)	−0.0064 (3)	0.0084 (3)	0.0042 (3)
C6	0.0262 (13)	0.0243 (13)	0.0137 (12)	−0.0005 (10)	0.0068 (11)	0.0018 (10)
C7	0.0225 (13)	0.0270 (14)	0.0115 (13)	0.0012 (10)	0.0053 (10)	0.0014 (10)
N1	0.0225 (11)	0.0289 (12)	0.0092 (10)	−0.0043 (9)	0.0069 (9)	−0.0008 (9)
C8	0.0207 (12)	0.0266 (13)	0.0114 (12)	−0.0019 (10)	0.0067 (10)	−0.0032 (9)
C9	0.0256 (13)	0.0275 (14)	0.0141 (13)	0.0000 (11)	0.0085 (11)	0.0030 (11)
C10	0.0376 (17)	0.0237 (14)	0.0233 (16)	−0.0026 (12)	0.0134 (14)	0.0027 (11)
C11	0.0348 (17)	0.0288 (15)	0.0274 (18)	−0.0101 (13)	0.0149 (14)	−0.0045 (13)
C12	0.0236 (13)	0.0322 (16)	0.0231 (16)	−0.0039 (11)	0.0070 (12)	−0.0050 (13)
C13	0.0224 (13)	0.0261 (13)	0.0139 (13)	0.0008 (10)	0.0073 (10)	−0.0032 (10)
C14	0.0252 (14)	0.0351 (16)	0.0181 (15)	−0.0001 (12)	0.0060 (12)	0.0004 (12)

Geometric parameters (Å, º) top

O1—C1	1.241 (4)	N1—H1	0.8800
C1—N1	1.346 (4)	C8—C9	1.399 (4)
C1—C2	1.505 (4)	C8—C13	1.402 (4)
C2—C3	1.396 (4)	C9—C10	1.388 (5)
C2—C7	1.404 (4)	C9—H9	0.9500
C3—C4	1.397 (4)	C10—C11	1.386 (5)
C3—Cl1	1.736 (3)	C10—H10	0.9500
C4—C5	1.398 (4)	C11—C12	1.389 (5)
C4—H4	0.9500	C11—H11	0.9500
C5—C6	1.388 (4)	C12—C13	1.412 (5)
C5—Cl2	1.733 (3)	C12—H12	0.9500
C6—C7	1.382 (5)	C13—C14	1.510 (5)
C6—H6	0.9500	C14—H14A	0.9800
C7—H7	0.9500	C14—H14B	0.9800
N1—C8	1.431 (4)	C14—H14C	0.9800

O1—C1—N1	124.6 (3)	C9—C8—C13	121.3 (3)
O1—C1—C2	120.3 (3)	C9—C8—N1	118.9 (3)
N1—C1—C2	115.1 (3)	C13—C8—N1	119.7 (3)
C3—C2—C7	118.4 (3)	C10—C9—C8	120.2 (3)
C3—C2—C1	120.8 (3)	C10—C9—H9	119.9
C7—C2—C1	120.8 (3)	C8—C9—H9	119.9
C2—C3—C4	121.3 (3)	C11—C10—C9	119.6 (3)
C2—C3—Cl1	120.0 (2)	C11—C10—H10	120.2
C4—C3—Cl1	118.7 (2)	C9—C10—H10	120.2
C3—C4—C5	118.2 (3)	C10—C11—C12	120.3 (3)
C3—C4—H4	120.9	C10—C11—H11	119.8
C5—C4—H4	120.9	C12—C11—H11	119.8
C6—C5—C4	121.8 (3)	C11—C12—C13	121.4 (3)
C6—C5—Cl2	119.9 (2)	C11—C12—H12	119.3
C4—C5—Cl2	118.3 (2)	C13—C12—H12	119.3
C7—C6—C5	118.8 (3)	C8—C13—C12	117.1 (3)
C7—C6—H6	120.6	C8—C13—C14	121.5 (3)
C5—C6—H6	120.6	C12—C13—C14	121.4 (3)
C6—C7—C2	121.5 (3)	C13—C14—H14A	109.5
C6—C7—H7	119.3	C13—C14—H14B	109.5
C2—C7—H7	119.3	H14A—C14—H14B	109.5
C1—N1—C8	123.1 (3)	C13—C14—H14C	109.5
C1—N1—H1	118.5	H14A—C14—H14C	109.5
C8—N1—H1	118.5	H14B—C14—H14C	109.5

O1—C1—C2—C3	66.1 (4)	C1—C2—C7—C6	176.2 (3)
N1—C1—C2—C3	−114.1 (3)	O1—C1—N1—C8	−7.1 (5)
O1—C1—C2—C7	−111.4 (4)	C2—C1—N1—C8	173.2 (3)
N1—C1—C2—C7	68.4 (4)	C1—N1—C8—C9	−50.9 (4)
C7—C2—C3—C4	0.3 (4)	C1—N1—C8—C13	130.9 (3)
C1—C2—C3—C4	−177.3 (3)	C13—C8—C9—C10	−1.0 (5)
C7—C2—C3—Cl1	−179.2 (2)	N1—C8—C9—C10	−179.1 (3)
C1—C2—C3—Cl1	3.2 (4)	C8—C9—C10—C11	0.4 (5)
C2—C3—C4—C5	1.2 (4)	C9—C10—C11—C12	0.8 (6)
Cl1—C3—C4—C5	−179.3 (2)	C10—C11—C12—C13	−1.6 (6)
C3—C4—C5—C6	−1.7 (5)	C9—C8—C13—C12	0.3 (5)
C3—C4—C5—Cl2	178.4 (2)	N1—C8—C13—C12	178.4 (3)
C4—C5—C6—C7	0.6 (5)	C9—C8—C13—C14	−180.0 (3)
Cl2—C5—C6—C7	−179.4 (2)	N1—C8—C13—C14	−1.8 (4)
C5—C6—C7—C2	1.0 (5)	C11—C12—C13—C8	1.0 (5)
C3—C2—C7—C6	−1.4 (5)	C11—C12—C13—C14	−178.8 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1ⁱ	0.88	2.04	2.865 (4)	156
C6—H6···O1ⁱⁱ	0.95	2.55	3.415 (4)	151
C11—H11···Cl2ⁱⁱⁱ	0.95	2.83	3.680 (3)	150
C14—H14C···Cg2ⁱ	0.98	2.87	3.528 (4)	125

Symmetry codes: (i) x, −y+1, z−1/2; (ii) x, −y+2, z−1/2; (iii) x−1/2, y−3/2, z.

Experimental details

Crystal data
Chemical formula	C₁₄H₁₁Cl₂NO
M_r	280.14
Crystal system, space group	Monoclinic, Cc
Temperature (K)	92
a, b, c (Å)	22.517 (4), 6.0405 (9), 9.6332 (17)
β (°)	104.838 (9)
V (Å³)	1266.6 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.50
Crystal size (mm)	0.46 × 0.27 × 0.19

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2006)
T_min, T_max	0.615, 0.91
No. of measured, independent and observed [I > 2σ(I)] reflections	9889, 3475, 3195
R_int	0.043
(sin θ/λ)_max (Å⁻¹)	0.768

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.057, 0.158, 1.15
No. of reflections	3475
No. of parameters	164
No. of restraints	2
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.36, −0.62
Absolute structure	Flack (1983), 1248 Friedel pairs
Absolute structure parameter	0.05 (8)

Computer programs: APEX2 (Bruker, 2006), APEX2 and SAINT (Bruker, 2006), SAINT (Bruker, 2006), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008) and TITAN (Hunter & Simpson, 1999), SHELXTL (Sheldrick, 2008) and Mercury (Macrae et al., 2006), SHELXL97 (Sheldrick, 2008), enCIFer (Allen et al., 2004), PLATON (Spek, 2009) and publCIF (Westrip, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1ⁱ	0.88	2.04	2.865 (4)	156
C6—H6···O1ⁱⁱ	0.95	2.55	3.415 (4)	151
C11—H11···Cl2ⁱⁱⁱ	0.95	2.83	3.680 (3)	150
C14—H14C···Cg2ⁱ	0.98	2.87	3.528 (4)	125

Symmetry codes: (i) x, −y+1, z−1/2; (ii) x, −y+2, z−1/2; (iii) x−1/2, y−3/2, z.

Acknowledgements

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

References

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