4-Chloro-N-(2,4-dimethyl­phenyl)­benzamide

Mol­ecules of the title compound, C₁₅H₁₄ClNO, are linked into chains along the c axis by inter­molecular N—H...O hydrogen bonds. The xylene and chloro­benzene rings deviate from the amide plane [C(=O)—N] by 77.8 (1) and 29.7 (1)°, respectively.

Key indicators

• Single-crystal X-ray study
• T = 294 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.047
• wR factor = 0.128
• Data-to-parameter ratio = 14.0

checkCIF/PLATON results

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S1. Comment

The bonds to nitrogen of the title amide (I), Fig.1, lie in the same plane (C7—N1—C8 123.92 (17), C7—N1—H1A 121.5 (16), C8—N1—H1A 114.5 (16)), unlike the pyramidal arrangement of bonds in ammonia and amines. The C7—N1 bond has considerable double-bond character, at 1.344 (3) Å, is substantially shorter than the normal C—N single-bond distance observed in amines. The dihedral angle between the xylene and chlorobenzene ring is 73.27 (11)°.

In the crystal of (I), the intermolecular N—H···O H-bonds (Table 1) linked molecules to chains along the c axis (Fig.2).

Related literature

For arylamides, see: Jackson et al. (2002); Gowda, Sowmya, Kožíšek et al. (2007); Gowda, Sowmya, Tokarčík et al. (2007a,b); Gowda, Foro et al. (2007).

S2. Experimental

The title compound was prepared, in a 90% yield, by reaction of 2,4-xylidine (1.21 g, 10 mmol) with 4-chlorobenzoyl chloride (1.92 g, 11 mmol) in CH₂Cl₂ (20 ml)in the presence of aqueous NaHCO₃ (1.68 g, 20 mmol). Colorless blocks of (I) were grown by natural evaporation of a MeOH solution.

S3. Refinement

The N-bound H atoms were refined freely while the other H atoms were positioned geometrically (C—H = 0.93 and 0.96 Å) and refined as riding with U_iso(H) = 1.2U_eq(C) or 1.5U_eq(methyl C).

Computing details

Data collection: SMART (Bruker, 1997); cell refinement: SMART (Bruker, 1997); data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL (Bruker, 1997).

Figures

	Fig. 1. The molecular structure of (I), with the atom-numbering scheme and 30% probability displacement ellipsoids for the non-hydrogen atoms.
	Fig. 2. A partial packing diagram for (1). The dashed lines indicate intermolecular hydrogen bonds.

4-Chloro-N-(2,4-dimethylphenyl)benzamide

Crystal data

C15H14ClNO	F(000) = 544
Mr = 259.72	Dx = 1.277 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2688 reflections
a = 22.918 (6) Å	θ = 3.1–26.3°
b = 6.4588 (17) Å	µ = 0.27 mm^−1
c = 9.261 (3) Å	T = 294 K
β = 99.654 (4)°	Block, colorless
V = 1351.4 (6) Å^3	0.30 × 0.26 × 0.20 mm
Z = 4

Data collection

Bruker SMART 1K CCD area-detector diffractometer	2367 independent reflections
Radiation source: fine-focus sealed tube	1861 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.023
ϕ and ω scans	θmax = 25.0°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −20→27
Tmin = 0.924, Tmax = 0.948	k = −7→5
4885 measured reflections	l = −11→8

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.128	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0514P)^2 + 0.7152P] where P = (Fo^2 + 2Fc^2)/3
2367 reflections	(Δ/σ)max = 0.002
169 parameters	Δρmax = 0.18 e Å^−3
1 restraint	Δρmin = −0.26 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
Cl1	0.03364 (4)	1.33583 (14)	0.65684 (12)	0.1027 (4)
O1	0.23813 (7)	0.5885 (2)	0.72579 (15)	0.0473 (4)
N1	0.25229 (8)	0.6922 (3)	0.96238 (18)	0.0454 (5)
C1	0.08899 (11)	1.1520 (4)	0.7080 (3)	0.0592 (7)
C2	0.08721 (11)	0.9683 (5)	0.6315 (3)	0.0646 (7)
H2	0.0567	0.9420	0.5539	0.077*
C3	0.13137 (10)	0.8242 (4)	0.6718 (3)	0.0519 (6)
H3	0.1306	0.7005	0.6202	0.062*
C4	0.17688 (9)	0.8604 (3)	0.7879 (2)	0.0389 (5)
C5	0.17761 (11)	1.0476 (4)	0.8624 (3)	0.0544 (6)
H5	0.2079	1.0747	0.9402	0.065*
C6	0.13392 (13)	1.1936 (4)	0.8224 (3)	0.0648 (7)
H6	0.1349	1.3188	0.8723	0.078*
C7	0.22494 (9)	0.7027 (3)	0.8224 (2)	0.0388 (5)
C8	0.30162 (9)	0.5585 (3)	1.0128 (2)	0.0393 (5)
C9	0.35792 (10)	0.6094 (3)	0.9857 (2)	0.0409 (5)
C10	0.40452 (10)	0.4800 (4)	1.0444 (2)	0.0453 (5)
H10	0.4424	0.5121	1.0278	0.054*
C11	0.39697 (10)	0.3051 (4)	1.1265 (2)	0.0480 (6)
C12	0.34021 (10)	0.2593 (4)	1.1516 (2)	0.0504 (6)
H12	0.3339	0.1436	1.2068	0.061*
C13	0.29303 (10)	0.3851 (4)	1.0947 (2)	0.0449 (5)
H13	0.2552	0.3529	1.1117	0.054*
C14	0.36859 (12)	0.7973 (4)	0.8979 (3)	0.0594 (7)
H14A	0.4104	0.8208	0.9065	0.089*
H14B	0.3503	0.9157	0.9343	0.089*
H14C	0.3519	0.7754	0.7969	0.089*
C15	0.44913 (13)	0.1704 (5)	1.1882 (3)	0.0760 (9)
H15A	0.4766	0.1661	1.1205	0.114*
H15B	0.4355	0.0328	1.2035	0.114*
H15C	0.4684	0.2268	1.2798	0.114*
H1A	0.2396 (10)	0.765 (3)	1.033 (2)	0.062 (7)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0736 (6)	0.0776 (6)	0.1499 (9)	0.0316 (4)	−0.0017 (5)	0.0127 (5)
O1	0.0544 (9)	0.0523 (9)	0.0344 (7)	0.0066 (8)	0.0053 (6)	−0.0048 (7)
N1	0.0505 (11)	0.0548 (12)	0.0307 (9)	0.0119 (9)	0.0064 (8)	−0.0029 (8)
C1	0.0461 (14)	0.0566 (15)	0.0749 (17)	0.0100 (12)	0.0105 (12)	0.0102 (13)
C2	0.0425 (14)	0.0704 (18)	0.0750 (17)	0.0028 (13)	−0.0070 (12)	0.0000 (15)
C3	0.0430 (13)	0.0528 (15)	0.0577 (14)	−0.0018 (11)	0.0023 (11)	−0.0071 (11)
C4	0.0379 (11)	0.0446 (12)	0.0350 (10)	−0.0015 (9)	0.0080 (8)	0.0023 (9)
C5	0.0602 (15)	0.0515 (14)	0.0473 (13)	0.0038 (12)	−0.0033 (11)	−0.0055 (11)
C6	0.0759 (19)	0.0464 (15)	0.0713 (17)	0.0099 (13)	0.0100 (14)	−0.0054 (13)
C7	0.0419 (12)	0.0420 (12)	0.0330 (10)	−0.0031 (9)	0.0078 (9)	−0.0006 (9)
C8	0.0447 (12)	0.0442 (12)	0.0278 (9)	0.0026 (10)	0.0025 (8)	−0.0043 (9)
C9	0.0467 (13)	0.0441 (12)	0.0320 (10)	−0.0026 (10)	0.0065 (9)	0.0005 (9)
C10	0.0394 (12)	0.0551 (14)	0.0414 (11)	−0.0040 (10)	0.0061 (9)	−0.0005 (10)
C11	0.0516 (14)	0.0462 (13)	0.0448 (12)	0.0038 (11)	0.0038 (10)	0.0012 (10)
C12	0.0598 (15)	0.0402 (12)	0.0508 (12)	−0.0046 (11)	0.0079 (11)	0.0071 (11)
C13	0.0442 (12)	0.0497 (13)	0.0415 (11)	−0.0067 (11)	0.0089 (9)	−0.0015 (10)
C14	0.0628 (16)	0.0573 (16)	0.0587 (14)	−0.0036 (13)	0.0120 (12)	0.0147 (12)
C15	0.0644 (18)	0.074 (2)	0.085 (2)	0.0148 (15)	0.0009 (15)	0.0197 (16)

Geometric parameters (Å, º)

Cl1—C1	1.744 (3)	C8—C9	1.395 (3)
O1—C7	1.236 (2)	C9—C10	1.393 (3)
N1—C7	1.344 (3)	C9—C14	1.503 (3)
N1—C8	1.437 (3)	C10—C11	1.388 (3)
N1—H1A	0.892 (10)	C10—H10	0.9300
C1—C6	1.374 (4)	C11—C12	1.391 (3)
C1—C2	1.379 (4)	C11—C15	1.511 (3)
C2—C3	1.380 (3)	C12—C13	1.384 (3)
C2—H2	0.9300	C12—H12	0.9300
C3—C4	1.387 (3)	C13—H13	0.9300
C3—H3	0.9300	C14—H14A	0.9600
C4—C5	1.390 (3)	C14—H14B	0.9600
C4—C7	1.495 (3)	C14—H14C	0.9600
C5—C6	1.380 (4)	C15—H15A	0.9600
C5—H5	0.9300	C15—H15B	0.9600
C6—H6	0.9300	C15—H15C	0.9600
C8—C13	1.386 (3)
C7—N1—C8	123.92 (17)	C10—C9—C8	117.4 (2)
C7—N1—H1A	121.5 (16)	C10—C9—C14	120.8 (2)
C8—N1—H1A	114.5 (16)	C8—C9—C14	121.8 (2)
C6—C1—C2	121.2 (2)	C11—C10—C9	123.0 (2)
C6—C1—Cl1	119.5 (2)	C11—C10—H10	118.5
C2—C1—Cl1	119.3 (2)	C9—C10—H10	118.5
C1—C2—C3	119.0 (2)	C10—C11—C12	118.1 (2)
C1—C2—H2	120.5	C10—C11—C15	120.8 (2)
C3—C2—H2	120.5	C12—C11—C15	121.1 (2)
C2—C3—C4	121.2 (2)	C13—C12—C11	120.3 (2)
C2—C3—H3	119.4	C13—C12—H12	119.9
C4—C3—H3	119.4	C11—C12—H12	119.9
C3—C4—C5	118.4 (2)	C12—C13—C8	120.6 (2)
C3—C4—C7	118.81 (19)	C12—C13—H13	119.7
C5—C4—C7	122.64 (19)	C8—C13—H13	119.7
C6—C5—C4	120.9 (2)	C9—C14—H14A	109.5
C6—C5—H5	119.6	C9—C14—H14B	109.5
C4—C5—H5	119.6	H14A—C14—H14B	109.5
C1—C6—C5	119.3 (2)	C9—C14—H14C	109.5
C1—C6—H6	120.3	H14A—C14—H14C	109.5
C5—C6—H6	120.3	H14B—C14—H14C	109.5
O1—C7—N1	122.50 (19)	C11—C15—H15A	109.5
O1—C7—C4	120.87 (17)	C11—C15—H15B	109.5
N1—C7—C4	116.63 (18)	H15A—C15—H15B	109.5
C13—C8—C9	120.7 (2)	C11—C15—H15C	109.5
C13—C8—N1	119.17 (19)	H15A—C15—H15C	109.5
C9—C8—N1	120.08 (19)	H15B—C15—H15C	109.5
C6—C1—C2—C3	0.3 (4)	C7—N1—C8—C13	−106.9 (2)
Cl1—C1—C2—C3	179.5 (2)	C7—N1—C8—C9	76.4 (3)
C1—C2—C3—C4	0.5 (4)	C13—C8—C9—C10	−0.2 (3)
C2—C3—C4—C5	−0.9 (4)	N1—C8—C9—C10	176.43 (18)
C2—C3—C4—C7	−177.3 (2)	C13—C8—C9—C14	−179.6 (2)
C3—C4—C5—C6	0.4 (4)	N1—C8—C9—C14	−3.0 (3)
C7—C4—C5—C6	176.7 (2)	C8—C9—C10—C11	0.4 (3)
C2—C1—C6—C5	−0.8 (4)	C14—C9—C10—C11	179.8 (2)
Cl1—C1—C6—C5	180.0 (2)	C9—C10—C11—C12	−0.5 (3)
C4—C5—C6—C1	0.4 (4)	C9—C10—C11—C15	−179.8 (2)
C8—N1—C7—O1	4.1 (3)	C10—C11—C12—C13	0.4 (3)
C8—N1—C7—C4	−176.16 (19)	C15—C11—C12—C13	179.7 (2)
C3—C4—C7—O1	27.6 (3)	C11—C12—C13—C8	−0.3 (3)
C5—C4—C7—O1	−148.7 (2)	C9—C8—C13—C12	0.2 (3)
C3—C4—C7—N1	−152.1 (2)	N1—C8—C13—C12	−176.50 (19)
C5—C4—C7—N1	31.6 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1^i	0.89 (1)	2.03 (1)	2.886 (2)	161 (2)

Symmetry code: (i) x, −y+3/2, z+1/2.