2,4-Dichloro-N-p-tolyl­benzamide

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

doi:10.1107/S1600536809034710

organic compounds

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ISSN: 2056-9890

Volume 65| Part 10| October 2009| Page o2527

doi:10.1107/S1600536809034710

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2,4-Dichloro-N-p-tolylbenzamide

Aamer Saeed,^a ^* Rasheed Ahmad Khera,^a Hummera Rafique,^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 2 July 2009; accepted 29 August 2009; online 26 September 2009)

In the title compound, C₁₄H₁₁Cl₂NO, the C—N—C(=O)—C amide unit is almost planar (r.m.s. deviation = 0.0317 Å) and subtends dihedral angles of 65.93 (6) and 29.45 (7)°, respectively, to the dichlorobenzene and tolyl rings. The two aromatic rings are inclined at 37.92 (6)° to one another. In the crystal structure, N—H⋯O hydrogen bonds link the molecules into chains along b. Additional weak C—H⋯Cl and C—H⋯O hydrogen bonds combine with C—H⋯π and very weak π–π contacts [Cg⋯Cg distance = 4.0217 (12) Å] to stack the molecules down b.

Related literature

For background to our work on benzamide derivatives, see: Saeed et al. (2008 ). For related structures see: Zhou & Zheng (2007 ); Gowda et al. (2008a ,b ,c , 2009 ); Chopra & Guru Row (2005 ).

Experimental

Crystal data

C₁₄H₁₁Cl₂NO
M_r = 280.14
Monoclinic, P 2₁ /c
a = 9.0884 (18) Å
b = 9.825 (2) Å
c = 14.167 (3) Å
β = 94.208 (9)°
V = 1261.6 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.50 mm⁻¹
T = 89 K
0.33 × 0.26 × 0.06 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2006 ) T_min = 0.753, T_max = 0.970
20982 measured reflections
4465 independent reflections
3463 reflections with I > 2σ(I)
R_int = 0.044

Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.132
S = 1.15
4465 reflections
167 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.57 e Å⁻³
Δρ_min = −0.49 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1ⁱ	0.86 (2)	2.14 (2)	2.9867 (17)	168 (2)
C12—H12⋯Cl1ⁱⁱ	0.95	2.91	3.7372 (17)	146
C6—H6⋯O1ⁱⁱⁱ	0.95	2.67	3.619 (2)	175
C7—H7⋯Cg2^iv	0.95	2.65	3.4865 (17)	147
Symmetry codes: (i) $[-x+1, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (ii) -x+1, -y+1, -z+2; (iii) $[x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ ; (iv) $[x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ . 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/S1600536809034710/fl2252sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809034710/fl2252Isup2.hkl

checkCIF report

Comment top

The background to our work on benzamide derivatives has been described in a previous paper (Saeed et al., 2008). In the title compound (I), Fig. 1, the C8–N1–C1(O1)–C2 amide unit is planar, r.m.s. deviation 0.0317 Å, and subtends dihedral angles of 65.93 (6)° and 29.45 (7)° respectively to the C2···C7 dichlorobenzene and C8···C13 tolyl rings. The two aromatic rings are inclined at 37.92 (6)° to one another. Bond distances within the molecule are normal and similar to those observed in comparable structures (Zhou & Zheng, 2007; Gowda et al. 2008a,b,c 2009; Chopra & Guru Row, 2005).

In the crystal structure N—H···O hydrogen bonds link molecules in a head to tail fashion into rows along b. C7—H7···π and weak, inversion related π–π contacts involving adjacent dichlorobenene rings [Cg···Cg distance 4.0217 (12), symmetry operation 1 - x, 1 - y, 1 - z] are also observed, Table 1, Fig 2. These together with additional C—H···Cl and C—H···O hydrogen bonds link the stacks of molecules alternately head to head and head to tail down the b axis, Fig. 3.

Related literature top

For background to our work on benzamide derivatives, see: Saeed et al. (2008). For related structures see: Zhou & Zheng (2007); Gowda et al. (2008a,b,c, 2009); Chopra & Guru Row (2005).

Experimental top

2,4-Dichlorobenzoyl chloride (5.4 mmol) in CHCl₃ was treated with p-toluidine(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 magnesium sulfate and concentrated under reduced pressure. Crystallization of the residue by evaporation from CHCl₃ afforded the title compound (84%) as colourless needles: Anal. calcd. for C₁₄H₁₁Cl₂NO,: C, 60.02; H, 3.96; N, 5.00%; found: C, 60.06; H, 3.92; N, 5.10%

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 TITAN2000 (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. π–π and C—H···π interactions in (I). Contacts are shown as dotted lines,the coloured spheres represent the ring centroids.
	Fig. 3. Crystal packing of (I) viewed down the b axis, with hydrogen bonds drawn as dashed lines.

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

Crystal data top

C₁₄H₁₁Cl₂NO	F(000) = 576
M_r = 280.14	D_x = 1.475 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5859 reflections
a = 9.0884 (18) Å	θ = 2.5–33.0°
b = 9.825 (2) Å	µ = 0.50 mm⁻¹
c = 14.167 (3) Å	T = 89 K
β = 94.208 (9)°	Irregular fragment, colourless
V = 1261.6 (4) Å³	0.33 × 0.26 × 0.06 mm
Z = 4

Data collection top

Bruker APEXII CCD diffractometer	4465 independent reflections
Radiation source: fine-focus sealed tube	3463 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.044
ω scans	θ_max = 33.1°, θ_min = 2.9°
Absorption correction: multi-scan (SADABS; Bruker, 2006)	h = −13→13
T_min = 0.753, T_max = 0.970	k = −14→13
20982 measured reflections	l = −21→21

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.132	H atoms treated by a mixture of independent and constrained refinement
S = 1.15	w = 1/[σ²(F_o²) + (0.0688P)² + 0.2064P] where P = (F_o² + 2F_c²)/3
4465 reflections	(Δ/σ)_max = 0.001
167 parameters	Δρ_max = 0.57 e Å⁻³
0 restraints	Δρ_min = −0.49 e Å⁻³

Crystal data top

C₁₄H₁₁Cl₂NO	V = 1261.6 (4) Å³
M_r = 280.14	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 9.0884 (18) Å	µ = 0.50 mm⁻¹
b = 9.825 (2) Å	T = 89 K
c = 14.167 (3) Å	0.33 × 0.26 × 0.06 mm
β = 94.208 (9)°

Data collection top

Bruker APEXII CCD diffractometer	4465 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2006)	3463 reflections with I > 2σ(I)
T_min = 0.753, T_max = 0.970	R_int = 0.044
20982 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	0 restraints
wR(F²) = 0.132	H atoms treated by a mixture of independent and constrained refinement
S = 1.15	Δρ_max = 0.57 e Å⁻³
4465 reflections	Δρ_min = −0.49 e Å⁻³
167 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	0.52742 (16)	0.71474 (14)	0.71812 (10)	0.0111 (3)
C2	0.43510 (16)	0.67111 (13)	0.63071 (10)	0.0105 (3)
C3	0.29263 (16)	0.61878 (14)	0.63334 (10)	0.0121 (3)
C4	0.21096 (16)	0.57806 (14)	0.55106 (10)	0.0126 (3)
H4	0.1147	0.5414	0.5539	0.015*
C5	0.27317 (16)	0.59219 (14)	0.46479 (10)	0.0125 (3)
C6	0.41328 (16)	0.64737 (14)	0.45883 (10)	0.0130 (3)
H6	0.4536	0.6584	0.3993	0.016*
C7	0.49281 (16)	0.68595 (14)	0.54224 (11)	0.0125 (3)
H7	0.5887	0.7233	0.5391	0.015*
C8	0.66786 (16)	0.62192 (14)	0.86070 (10)	0.0109 (3)
C9	0.77909 (17)	0.71922 (15)	0.87165 (11)	0.0141 (3)
H9	0.7902	0.7855	0.8239	0.017*
C10	0.87396 (17)	0.71820 (15)	0.95361 (11)	0.0153 (3)
H10	0.9498	0.7847	0.9607	0.018*
C11	0.86130 (16)	0.62256 (14)	1.02572 (11)	0.0131 (3)
C12	0.74965 (17)	0.52520 (15)	1.01274 (11)	0.0142 (3)
H12	0.7388	0.4585	1.0603	0.017*
C13	0.65393 (16)	0.52412 (14)	0.93137 (10)	0.0123 (3)
H13	0.5789	0.4568	0.9238	0.015*
C14	0.96308 (18)	0.62590 (17)	1.11523 (11)	0.0184 (3)
H14A	0.9120	0.6683	1.1662	0.028*
H14B	1.0515	0.6788	1.1040	0.028*
H14C	0.9916	0.5328	1.1334	0.028*
N1	0.56897 (14)	0.61267 (12)	0.77821 (9)	0.0120 (2)
O1	0.56444 (13)	0.83472 (10)	0.72985 (8)	0.0168 (2)
Cl1	0.20933 (4)	0.60815 (4)	0.73967 (3)	0.01815 (11)
Cl2	0.17246 (4)	0.53821 (4)	0.36221 (3)	0.01910 (11)
H1N	0.530 (2)	0.534 (2)	0.7672 (16)	0.023*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0116 (6)	0.0104 (6)	0.0112 (6)	0.0005 (5)	0.0004 (5)	0.0007 (5)
C2	0.0122 (6)	0.0073 (6)	0.0117 (6)	0.0008 (4)	−0.0010 (5)	0.0009 (4)
C3	0.0135 (6)	0.0120 (6)	0.0107 (6)	0.0020 (5)	0.0011 (5)	0.0023 (5)
C4	0.0108 (6)	0.0127 (6)	0.0141 (7)	−0.0008 (5)	−0.0005 (5)	0.0009 (5)
C5	0.0145 (6)	0.0111 (6)	0.0115 (6)	0.0015 (5)	−0.0020 (5)	−0.0012 (5)
C6	0.0154 (6)	0.0114 (6)	0.0123 (6)	0.0003 (5)	0.0022 (5)	0.0005 (5)
C7	0.0127 (6)	0.0095 (6)	0.0153 (7)	−0.0011 (5)	0.0005 (5)	0.0005 (5)
C8	0.0121 (6)	0.0091 (6)	0.0112 (6)	0.0016 (4)	−0.0006 (5)	−0.0013 (4)
C9	0.0154 (6)	0.0127 (6)	0.0137 (6)	−0.0026 (5)	−0.0014 (5)	0.0035 (5)
C10	0.0141 (7)	0.0134 (6)	0.0179 (7)	−0.0031 (5)	−0.0015 (6)	0.0003 (5)
C11	0.0117 (6)	0.0141 (6)	0.0133 (6)	0.0011 (5)	−0.0008 (5)	−0.0002 (5)
C12	0.0166 (7)	0.0131 (6)	0.0125 (6)	−0.0014 (5)	−0.0008 (5)	0.0026 (5)
C13	0.0130 (6)	0.0103 (6)	0.0134 (6)	−0.0019 (5)	−0.0001 (5)	0.0005 (5)
C14	0.0182 (7)	0.0217 (7)	0.0145 (7)	−0.0031 (6)	−0.0037 (6)	0.0012 (6)
N1	0.0154 (6)	0.0084 (5)	0.0115 (6)	−0.0014 (4)	−0.0034 (5)	0.0006 (4)
O1	0.0210 (6)	0.0084 (5)	0.0199 (5)	−0.0009 (4)	−0.0056 (4)	0.0009 (4)
Cl1	0.01473 (18)	0.0284 (2)	0.01157 (18)	0.00040 (13)	0.00261 (13)	0.00371 (13)
Cl2	0.01772 (19)	0.0254 (2)	0.01362 (18)	−0.00149 (13)	−0.00263 (14)	−0.00494 (13)

Geometric parameters (Å, º) top

C1—O1	1.2338 (17)	C8—C13	1.400 (2)
C1—N1	1.3512 (18)	C8—N1	1.4240 (18)
C1—C2	1.5062 (19)	C9—C10	1.395 (2)
C2—C3	1.396 (2)	C9—H9	0.9500
C2—C7	1.401 (2)	C10—C11	1.399 (2)
C3—C4	1.394 (2)	C10—H10	0.9500
C3—Cl1	1.7379 (16)	C11—C12	1.397 (2)
C4—C5	1.391 (2)	C11—C14	1.514 (2)
C4—H4	0.9500	C12—C13	1.392 (2)
C5—C6	1.392 (2)	C12—H12	0.9500
C5—Cl2	1.7423 (15)	C13—H13	0.9500
C6—C7	1.392 (2)	C14—H14A	0.9800
C6—H6	0.9500	C14—H14B	0.9800
C7—H7	0.9500	C14—H14C	0.9800
C8—C9	1.392 (2)	N1—H1N	0.86 (2)

O1—C1—N1	124.29 (13)	C8—C9—C10	119.17 (13)
O1—C1—C2	120.84 (12)	C8—C9—H9	120.4
N1—C1—C2	114.82 (12)	C10—C9—H9	120.4
C3—C2—C7	118.10 (13)	C9—C10—C11	122.27 (14)
C3—C2—C1	122.99 (13)	C9—C10—H10	118.9
C7—C2—C1	118.90 (13)	C11—C10—H10	118.9
C4—C3—C2	121.42 (14)	C12—C11—C10	117.50 (13)
C4—C3—Cl1	117.94 (12)	C12—C11—C14	121.22 (14)
C2—C3—Cl1	120.61 (11)	C10—C11—C14	121.27 (13)
C5—C4—C3	118.71 (14)	C13—C12—C11	121.19 (14)
C5—C4—H4	120.6	C13—C12—H12	119.4
C3—C4—H4	120.6	C11—C12—H12	119.4
C4—C5—C6	121.66 (13)	C12—C13—C8	120.20 (13)
C4—C5—Cl2	118.69 (11)	C12—C13—H13	119.9
C6—C5—Cl2	119.65 (12)	C8—C13—H13	119.9
C7—C6—C5	118.36 (14)	C11—C14—H14A	109.5
C7—C6—H6	120.8	C11—C14—H14B	109.5
C5—C6—H6	120.8	H14A—C14—H14B	109.5
C6—C7—C2	121.72 (13)	C11—C14—H14C	109.5
C6—C7—H7	119.1	H14A—C14—H14C	109.5
C2—C7—H7	119.1	H14B—C14—H14C	109.5
C9—C8—C13	119.66 (13)	C1—N1—C8	126.87 (12)
C9—C8—N1	123.01 (13)	C1—N1—H1N	117.5 (14)
C13—C8—N1	117.28 (12)	C8—N1—H1N	115.6 (14)

O1—C1—C2—C3	−115.79 (17)	C1—C2—C7—C6	179.87 (12)
N1—C1—C2—C3	66.64 (18)	C13—C8—C9—C10	−0.6 (2)
O1—C1—C2—C7	62.85 (19)	N1—C8—C9—C10	−178.01 (14)
N1—C1—C2—C7	−114.72 (15)	C8—C9—C10—C11	−0.1 (2)
C7—C2—C3—C4	2.0 (2)	C9—C10—C11—C12	0.6 (2)
C1—C2—C3—C4	−179.31 (13)	C9—C10—C11—C14	−178.33 (15)
C7—C2—C3—Cl1	−175.69 (10)	C10—C11—C12—C13	−0.5 (2)
C1—C2—C3—Cl1	2.96 (19)	C14—C11—C12—C13	178.50 (14)
C2—C3—C4—C5	−0.9 (2)	C11—C12—C13—C8	−0.2 (2)
Cl1—C3—C4—C5	176.86 (11)	C9—C8—C13—C12	0.8 (2)
C3—C4—C5—C6	−0.9 (2)	N1—C8—C13—C12	178.32 (13)
C3—C4—C5—Cl2	178.77 (11)	O1—C1—N1—C8	−4.3 (2)
C4—C5—C6—C7	1.5 (2)	C2—C1—N1—C8	173.21 (13)
Cl2—C5—C6—C7	−178.17 (11)	C9—C8—N1—C1	−26.7 (2)
C5—C6—C7—C2	−0.3 (2)	C13—C8—N1—C1	155.92 (15)
C3—C2—C7—C6	−1.4 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1ⁱ	0.86 (2)	2.14 (2)	2.9867 (17)	168 (2)
C12—H12···Cl1ⁱⁱ	0.95	2.91	3.7372 (17)	146
C6—H6···O1ⁱⁱⁱ	0.95	2.67	3.619 (2)	175
C7—H7···Cg2^iv	0.95	2.65	3.4865 (17)	147

Symmetry codes: (i) −x+1, y−1/2, −z+3/2; (ii) −x+1, −y+1, −z+2; (iii) x, −y+3/2, z−1/2; (iv) 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)	89
a, b, c (Å)	9.0884 (18), 9.825 (2), 14.167 (3)
β (°)	94.208 (9)
V (Å³)	1261.6 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.50
Crystal size (mm)	0.33 × 0.26 × 0.06

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2006)
T_min, T_max	0.753, 0.970
No. of measured, independent and observed [I > 2σ(I)] reflections	20982, 4465, 3463
R_int	0.044
(sin θ/λ)_max (Å⁻¹)	0.769

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.132, 1.15
No. of reflections	4465
No. of parameters	167
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.57, −0.49

Computer programs: APEX2 (Bruker, 2006), APEX2 and SAINT (Bruker, 2006), SAINT (Bruker, 2006), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008) and TITAN2000 (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—H1N···O1ⁱ	0.86 (2)	2.14 (2)	2.9867 (17)	168 (2)
C12—H12···Cl1ⁱⁱ	0.95	2.91	3.7372 (17)	145.8
C6—H6···O1ⁱⁱⁱ	0.95	2.67	3.619 (2)	174.8
C7—H7···Cg2^iv	0.95	2.65	3.4865 (17)	147

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

Acknowledgements

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

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