2-Chloro-N-(3,5-dimethyl-phen-yl)benzamide.

In the structure of the the title compound, C(15)H(14)ClNO, the N-H and C=O bonds are trans to each other and the amide O atom is anti to the ortho-Cl atom in the benzoyl ring. The amide group makes dihedral angles of 61.2 (6) and 42.2 (8)° with the benzoyl and aniline rings, respectively. In the crystal, the mol-ecules are linked into infinite chains by N-H⋯O hydrogen bonds.

Related literature

For the synthesis, see: Gowda et al. (2003 ▶). For structure of the 3,5-dichloro­phenyl analog and other benzanilides, see: Gowda et al. (2008 ▶).

Experimental

Crystal data

C15H14ClNO

M = 259.72

Orthorhombic,

a = 9.1867 (6) Å

b = 13.9710 (8) Å

c = 10.2711 (7) Å

V = 1318.27 (15) Å3

Z = 4

Mo Kα radiation

μ = 0.28 mm−1

T = 100 (2) K

0.48 × 0.28 × 0.13 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007 ▶) T min = 0.879, T max = 0.965

6034 measured reflections

2136 independent reflections

1977 reflections with I > 2σ(I)

R int = 0.014

Refinement

R[F 2 > 2σ(F 2)] = 0.031

wR(F 2) = 0.083

S = 1.03

2136 reflections

187 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.34 e Å−3

Δρmin = −0.27 e Å−3

Absolute structure: Flack (1983 ▶), 712 Friedel pairs

Flack parameter: 0.01 (7)

Data collection: CrysAlis CCD (Oxford Diffraction, 2007 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2007 ▶); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2003 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809001706/ng2536sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809001706/ng2536Isup2.hkl

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

C15H14ClNO	F(000) = 544
Mr = 259.72	Dx = 1.309 Mg m−3
Orthorhombic, Pna21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 2104 reflections
a = 9.1867 (6) Å	θ = 2.5–28.1°
b = 13.9710 (8) Å	µ = 0.28 mm−1
c = 10.2711 (7) Å	T = 100 K
V = 1318.27 (15) Å3	Prism, colourless
Z = 4	0.48 × 0.28 × 0.13 mm

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	2136 independent reflections
Radiation source: fine-focus sealed tube	1977 reflections with I > 2σ(I)
graphite	Rint = 0.014
Rotation method data acquisition using ω and φ scans	θmax = 26.4°, θmin = 2.5°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007)	h = −11→11
Tmin = 0.879, Tmax = 0.965	k = −17→17
6034 measured reflections	l = −10→12

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)] = 0.031	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.083	w = 1/[σ2(Fo2) + (0.0477P)2 + 0.598P] where P = (Fo2 + 2Fc2)/3
S = 1.02	(Δ/σ)max = 0.002
2136 reflections	Δρmax = 0.34 e Å−3
187 parameters	Δρmin = −0.27 e Å−3
2 restraints	Absolute structure: Flack (1983), 712 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.01 (7)

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
Cl1	0.11485 (6)	0.32674 (4)	1.16333 (7)	0.03305 (16)
O1	0.19372 (16)	0.32548 (10)	0.85807 (18)	0.0253 (4)
N1	−0.01100 (18)	0.24094 (12)	0.8052 (2)	0.0210 (4)
H1N	−0.0995 (19)	0.2359 (18)	0.820 (3)	0.025*
C1	0.0540 (2)	0.17351 (13)	0.7178 (2)	0.0211 (4)
C2	0.0112 (2)	0.07840 (15)	0.7257 (3)	0.0247 (5)
H2	−0.049 (3)	0.0577 (18)	0.794 (3)	0.030*
C3	0.0694 (2)	0.01080 (14)	0.6398 (3)	0.0299 (6)
C4	0.1719 (3)	0.04035 (16)	0.5498 (3)	0.0307 (5)
H4	0.219 (3)	−0.0046 (18)	0.489 (3)	0.037*
C5	0.2166 (3)	0.13617 (16)	0.5410 (2)	0.0287 (5)
C6	0.1549 (2)	0.20260 (15)	0.6256 (2)	0.0249 (5)
H6	0.192 (3)	0.2682 (18)	0.617 (3)	0.030*
C7	0.0614 (2)	0.31152 (14)	0.8664 (2)	0.0200 (4)
C8	−0.0321 (2)	0.37827 (13)	0.9446 (2)	0.0193 (4)
C9	−0.0080 (2)	0.39557 (15)	1.0757 (2)	0.0237 (5)
C10	−0.0849 (3)	0.46637 (16)	1.1420 (2)	0.0289 (5)
H10	−0.068 (3)	0.4734 (19)	1.232 (3)	0.035*
C11	−0.1868 (2)	0.52064 (16)	1.0761 (3)	0.0313 (6)
H11	−0.240 (3)	0.5734 (18)	1.117 (3)	0.038*
C12	−0.2157 (3)	0.50321 (15)	0.9463 (3)	0.0305 (5)
H12	−0.285 (3)	0.539 (2)	0.907 (3)	0.037*
C13	−0.1396 (2)	0.43181 (16)	0.8809 (3)	0.0239 (5)
H13	−0.157 (3)	0.4197 (18)	0.798 (3)	0.029*
C14	0.0200 (3)	−0.09234 (15)	0.6467 (4)	0.0409 (7)
H14A	0.0078	−0.1111	0.7380	0.049*
H14B	0.0932	−0.1335	0.6057	0.049*
H14C	−0.0729	−0.0993	0.6008	0.049*
C15	0.3281 (3)	0.16747 (18)	0.4422 (3)	0.0392 (6)
H15A	0.2854	0.1645	0.3548	0.047*
H15B	0.4128	0.1250	0.4465	0.047*
H15C	0.3585	0.2333	0.4610	0.047*

	U11	U22	U33	U12	U13	U23
Cl1	0.0362 (3)	0.0325 (3)	0.0304 (3)	−0.0048 (2)	−0.0079 (3)	0.0058 (3)
O1	0.0141 (7)	0.0272 (7)	0.0345 (10)	−0.0016 (5)	0.0019 (7)	−0.0081 (7)
N1	0.0133 (8)	0.0218 (8)	0.0280 (10)	−0.0020 (6)	0.0015 (8)	−0.0034 (7)
C1	0.0164 (9)	0.0219 (10)	0.0249 (11)	0.0019 (7)	−0.0043 (9)	−0.0049 (8)
C2	0.0178 (9)	0.0242 (10)	0.0323 (13)	−0.0008 (8)	−0.0045 (10)	−0.0028 (9)
C3	0.0219 (10)	0.0225 (9)	0.0454 (16)	0.0042 (7)	−0.0137 (11)	−0.0063 (10)
C4	0.0269 (11)	0.0306 (11)	0.0345 (14)	0.0099 (9)	−0.0078 (11)	−0.0150 (10)
C5	0.0261 (11)	0.0337 (11)	0.0262 (14)	0.0060 (9)	−0.0032 (11)	−0.0064 (10)
C6	0.0238 (10)	0.0221 (10)	0.0286 (13)	0.0010 (8)	−0.0015 (9)	−0.0030 (8)
C7	0.0180 (10)	0.0211 (9)	0.0208 (12)	−0.0005 (7)	0.0029 (9)	−0.0011 (8)
C8	0.0172 (9)	0.0188 (9)	0.0220 (12)	−0.0048 (7)	0.0034 (9)	−0.0019 (8)
C9	0.0211 (9)	0.0228 (10)	0.0273 (13)	−0.0085 (8)	0.0010 (9)	0.0008 (8)
C10	0.0351 (12)	0.0282 (10)	0.0235 (14)	−0.0127 (8)	0.0098 (11)	−0.0094 (9)
C11	0.0271 (11)	0.0249 (10)	0.0418 (16)	−0.0037 (8)	0.0135 (11)	−0.0097 (10)
C12	0.0221 (11)	0.0270 (11)	0.0424 (16)	0.0016 (9)	0.0052 (12)	−0.0005 (10)
C13	0.0188 (10)	0.0279 (10)	0.0250 (13)	−0.0015 (8)	0.0016 (9)	−0.0032 (9)
C14	0.0319 (12)	0.0227 (10)	0.068 (2)	0.0007 (8)	−0.0118 (14)	−0.0102 (13)
C15	0.0412 (14)	0.0471 (14)	0.0294 (14)	0.0052 (12)	0.0090 (13)	−0.0100 (12)

Cl1—C9	1.735 (2)	C8—C9	1.386 (3)
O1—C7	1.234 (3)	C8—C13	1.401 (3)
N1—C7	1.346 (3)	C9—C10	1.393 (3)
N1—C1	1.431 (3)	C10—C11	1.383 (4)
N1—H1N	0.831 (17)	C10—H10	0.94 (3)
C1—C6	1.386 (3)	C11—C12	1.380 (4)
C1—C2	1.388 (3)	C11—H11	0.98 (3)
C2—C3	1.399 (3)	C12—C13	1.391 (3)
C2—H2	0.94 (3)	C12—H12	0.91 (3)
C3—C4	1.382 (4)	C13—H13	0.89 (3)
C3—C14	1.512 (3)	C14—H14A	0.9800
C4—C5	1.403 (3)	C14—H14B	0.9800
C4—H4	0.99 (3)	C14—H14C	0.9800
C5—C6	1.392 (3)	C15—H15A	0.9800
C5—C15	1.506 (4)	C15—H15B	0.9800
C6—H6	0.98 (3)	C15—H15C	0.9800
C7—C8	1.501 (3)
C7—N1—C1	124.70 (17)	C8—C9—C10	121.2 (2)
C7—N1—H1N	117.2 (19)	C8—C9—Cl1	120.74 (16)
C1—N1—H1N	118.1 (19)	C10—C9—Cl1	118.02 (19)
C6—C1—C2	120.7 (2)	C11—C10—C9	119.5 (2)
C6—C1—N1	120.94 (18)	C11—C10—H10	122.3 (18)
C2—C1—N1	118.4 (2)	C9—C10—H10	118.1 (18)
C1—C2—C3	120.1 (2)	C12—C11—C10	120.4 (2)
C1—C2—H2	120.5 (16)	C12—C11—H11	116.7 (18)
C3—C2—H2	119.2 (16)	C10—C11—H11	122.8 (18)
C4—C3—C2	118.7 (2)	C11—C12—C13	119.8 (2)
C4—C3—C14	121.3 (2)	C11—C12—H12	118 (2)
C2—C3—C14	119.9 (2)	C13—C12—H12	122 (2)
C3—C4—C5	121.8 (2)	C12—C13—C8	120.7 (2)
C3—C4—H4	122.2 (16)	C12—C13—H13	120.8 (17)
C5—C4—H4	116.0 (16)	C8—C13—H13	118.5 (17)
C6—C5—C4	118.4 (2)	C3—C14—H14A	109.5
C6—C5—C15	120.3 (2)	C3—C14—H14B	109.5
C4—C5—C15	121.3 (2)	H14A—C14—H14B	109.5
C1—C6—C5	120.2 (2)	C3—C14—H14C	109.5
C1—C6—H6	124.8 (16)	H14A—C14—H14C	109.5
C5—C6—H6	114.9 (16)	H14B—C14—H14C	109.5
O1—C7—N1	124.76 (19)	C5—C15—H15A	109.5
O1—C7—C8	120.18 (18)	C5—C15—H15B	109.5
N1—C7—C8	115.01 (18)	H15A—C15—H15B	109.5
C9—C8—C13	118.23 (19)	C5—C15—H15C	109.5
C9—C8—C7	122.49 (19)	H15A—C15—H15C	109.5
C13—C8—C7	119.0 (2)	H15B—C15—H15C	109.5
C7—N1—C1—C6	−42.6 (3)	O1—C7—C8—C9	−57.9 (3)
C7—N1—C1—C2	138.7 (2)	N1—C7—C8—C9	124.6 (2)
C6—C1—C2—C3	−0.3 (3)	O1—C7—C8—C13	116.2 (2)
N1—C1—C2—C3	178.36 (19)	N1—C7—C8—C13	−61.3 (3)
C1—C2—C3—C4	1.4 (3)	C13—C8—C9—C10	−2.1 (3)
C1—C2—C3—C14	−178.6 (2)	C7—C8—C9—C10	172.08 (18)
C2—C3—C4—C5	−1.2 (4)	C13—C8—C9—Cl1	175.77 (15)
C14—C3—C4—C5	178.8 (2)	C7—C8—C9—Cl1	−10.1 (3)
C3—C4—C5—C6	−0.2 (4)	C8—C9—C10—C11	−0.2 (3)
C3—C4—C5—C15	−179.8 (2)	Cl1—C9—C10—C11	−178.07 (16)
C2—C1—C6—C5	−1.1 (3)	C9—C10—C11—C12	1.9 (3)
N1—C1—C6—C5	−179.7 (2)	C10—C11—C12—C13	−1.3 (3)
C4—C5—C6—C1	1.3 (3)	C11—C12—C13—C8	−1.1 (3)
C15—C5—C6—C1	−179.0 (2)	C9—C8—C13—C12	2.7 (3)
C1—N1—C7—O1	−2.2 (4)	C7—C8—C13—C12	−171.68 (19)
C1—N1—C7—C8	175.16 (19)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1i	0.83 (2)	2.12 (2)	2.918 (2)	161 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1i	0.831 (17)	2.120 (18)	2.918 (2)	161 (2)

Symmetry code: (i) .