2,4-Dichloro-N-p-tolyl-benzamide.

In the title compound, C(14)H(11)Cl(2)NO, 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 dichloro-benzene 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 mol-ecules 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 mol-ecules 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 = 280.14

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.132

S = 1.15

4465 reflections

167 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.57 e Å−3

Δρmin = −0.49 e Å−3

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 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809034710/fl2252sup1.cif

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

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C14H11Cl2NO	F(000) = 576
Mr = 280.14	Dx = 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

Bruker APEXII CCD diffractometer	4465 independent reflections
Radiation source: fine-focus sealed tube	3463 reflections with I > 2σ(I)
graphite	Rint = 0.044
ω scans	θmax = 33.1°, θmin = 2.9°
Absorption correction: multi-scan (SADABS; Bruker, 2006)	h = −13→13
Tmin = 0.753, Tmax = 0.970	k = −14→13
20982 measured reflections	l = −21→21

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(Fo2) + (0.0688P)2 + 0.2064P] where P = (Fo2 + 2Fc2)/3
4465 reflections	(Δ/σ)max = 0.001
167 parameters	Δρmax = 0.57 e Å−3
0 restraints	Δρmin = −0.48 e Å−3

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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···Cg2iv	0.95	2.65	3.4865 (17)	147

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⋯Cg2iv	0.95	2.65	3.4865 (17)	147

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) . Cg2 is the centroid of the C8–C13 ring.