N-(2,3-Dimethyl­phen­yl)-4-methylbenzamide

Rodrigues, V.Z.; Herich, P.; Gowda, B.T.; Kožíšek, J.

doi:10.1107/S1600536811034490

organic compounds

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ISSN: 2056-9890

Volume 67| Part 9| September 2011| Page o2463

doi:10.1107/S1600536811034490

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N-(2,3-Dimethylphenyl)-4-methylbenzamide

Vinola Z. Rodrigues,^a Peter Herich,^b B. Thimme Gowda ^a ^* and Jozef Kožíšek ^b

^aDepartment of Chemistry, Mangalore University, Mangalagangotri 574 199, Mangalore, India, and ^bInstitute of Physical Chemistry and Chemical Physics, Slovak University of Technology, Radlinského 9, SK-812 37 Bratislava, Slovak Republic
^*Correspondence e-mail: gowdabt@yahoo.com

(Received 19 August 2011; accepted 22 August 2011; online 27 August 2011)

In the molecule of the title compound, C₁₆H₁₇NO, the two aromatic rings are almost perpendicular to each other [dihedral angle 85.90 (5)°]. The crystal structure is stabilized by intermolecular N—H⋯O hydrogen bonds which link the molecules, forming C(4) chains running along the c axis.

Related literature

For preparation of the title compound, see: Gowda et al. (2003 ). For the study of the effect of substituents on the structures and other aspects of N-(aryl)amides, see: Arjunan et al. (2004 ); Bhat & Gowda (2000 ); Bowes et al. (2003 ); Gowda et al. (2009 ); Rodrigues et al. (2011 ); Saeed et al. (2010 ).

Experimental

Crystal data

C₁₆H₁₇NO
M_r = 239.31
Monoclinic, P 2₁ /c
a = 8.1723 (3) Å
b = 19.3923 (7) Å
c = 9.3170 (3) Å
β = 111.781 (4)°
V = 1371.14 (9) Å³
Z = 4
Mo Kα radiation
μ = 0.07 mm⁻¹
T = 293 K
0.76 × 0.12 × 0.09 mm

Data collection

Oxford Xcalibur Ruby Gemini diffractometer
Absorption correction: analytical [CrysAlis RED (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ) based on Clark & Reid (1995 )] T_min = 0.989, T_max = 0.994
21529 measured reflections
3806 independent reflections
1925 reflections with I > 2σ(I)
R_int = 0.030

Refinement

R[F² > 2σ(F²)] = 0.042
wR(F²) = 0.126
S = 0.93
3806 reflections
166 parameters
H-atom parameters constrained
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.18 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O1ⁱ	0.86	2.20	2.9256 (12)	143
Symmetry code: (i) $[x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2002 ); software used to prepare material for publication: enCIFer (Allen et al., 2004 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811034490/bt5622sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811034490/bt5622Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811034490/bt5622Isup3.cml

checkCIF report

Comment top

The structural aspects of N-aryl amides are of interest due to their chemical and biological importance (Arjunan et al., 2004; Bhat & Gowda, 2000; Bowes et al., 2003; Gowda et al., 2003; Saeed et al., 2010). In the present work, as part of a study of the substituent effects on the structures of benzanilides (Gowda et al., 2003, 2009; Rodrigues et al., 2011), the structure of 4-methyl-N-(2,3-dimethylphenyl)benzamide (I) has been determined (Fig. 1). In the crystal, the ortho- and meta-methyl substituents in the anilino ring are positioned anti to the N—H bond, similar to that observed in one of the molecules of 4-methyl-N-(2-methylphenyl)benzamide (II) (Rodrigues et al., 2011).

The central amide group –NHCO– is tilted to the anilino ring with the C10—C9—N1—C1 and C14—C9—N1—C1 torsion angles of -63.4 (2)° and 118.1 (1)°. The C3—C2—C1—N1 and C7—C2—C1—N1 torsion angles are -24.4 (2)° and 156.8 (1)°, respectively, while the C3—C2—C1—O1 and C7—C2—C1—O1 torsion angles are 155.6 (1)° and -23.2 (2)°, respectively. But the C2—C1—N1—C9 and C9—N1—C1—O1 torsion angles are -179.5 (1)° and 0.5 (2)°, respectively.

The packing of molecules linked by N—H···O hydrogen bonds is shown in Fig. 2.

Related literature top

For preparation of the title compound, see: Gowda et al. (2003). For the study of the effect of substituents on the structures and other aspects of N-(aryl)amides, see: Arjunan et al. (2004); Bhat & Gowda (2000); Bowes et al. (2003); Gowda et al. (2009); Rodrigues et al. (2011); Saeed et al. (2010).

Experimental top

The title compound was prepared according to the method described by Gowda et al. (2003). The purity of the compound was checked by determining its melting point. It was characterized by recording its infrared and NMR spectra. Cuboid-like colourless single crystals of the title compound were obtained by slow evaporation from an ethanol solution of the compound (0.5 g in about 30 ml of ethanol) at room temperature.

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2009); cell refinement: CrysAlis CCD (Oxford Diffraction, 2009); data reduction: CrysAlis RED (Oxford Diffraction, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2002); software used to prepare material for publication: enCIFer (Allen et al., 2004).

Figures top

	Fig. 1. Molecular structure of the title compound showing the atom labelling scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are represented as small spheres of arbitrary radii.
	Fig. 2. Part of the crystal structure of the title compound generated by N—H···O hydrogen bonds which are shown by dashed lines. H atoms not involved in intermolecular bonding have been omitted.

N-(2,3-Dimethylphenyl)-4-methylbenzamide top

Crystal data top

C₁₆H₁₇NO	F(000) = 512
M_r = 239.31	D_x = 1.159 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 7558 reflections
a = 8.1723 (3) Å	θ = 3.5–29.5°
b = 19.3923 (7) Å	µ = 0.07 mm⁻¹
c = 9.3170 (3) Å	T = 293 K
β = 111.781 (4)°	Cuboid, colourless
V = 1371.14 (9) Å³	0.76 × 0.12 × 0.09 mm
Z = 4

Data collection top

Oxford Xcalibur Ruby Gemini diffractometer	3806 independent reflections
Radiation source: fine-focus sealed tube	1925 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.030
Detector resolution: 10.4340 pixels mm^-1	θ_max = 29.5°, θ_min = 3.5°
ω scans	h = −10→11
Absorption correction: analytical [CrysAlis RED (Oxford Diffraction, 2009). Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by Clark & Reid (1995).]	k = −24→26
T_min = 0.989, T_max = 0.994	l = −12→12
21529 measured reflections

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.126	H-atom parameters constrained
S = 0.93	w = 1/[σ²(F_o²) + (0.0738P)²] where P = (F_o² + 2F_c²)/3
3806 reflections	(Δ/σ)_max = 0.001
166 parameters	Δρ_max = 0.20 e Å⁻³
0 restraints	Δρ_min = −0.18 e Å⁻³

Crystal data top

C₁₆H₁₇NO	V = 1371.14 (9) Å³
M_r = 239.31	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 8.1723 (3) Å	µ = 0.07 mm⁻¹
b = 19.3923 (7) Å	T = 293 K
c = 9.3170 (3) Å	0.76 × 0.12 × 0.09 mm
β = 111.781 (4)°

Data collection top

Oxford Xcalibur Ruby Gemini diffractometer	3806 independent reflections
Absorption correction: analytical [CrysAlis RED (Oxford Diffraction, 2009). Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by Clark & Reid (1995).]	1925 reflections with I > 2σ(I)
T_min = 0.989, T_max = 0.994	R_int = 0.030
21529 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	0 restraints
wR(F²) = 0.126	H-atom parameters constrained
S = 0.93	Δρ_max = 0.20 e Å⁻³
3806 reflections	Δρ_min = −0.18 e Å⁻³
166 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	0.73885 (17)	0.70346 (6)	0.43887 (13)	0.0447 (3)
C2	0.84624 (17)	0.65196 (6)	0.39419 (13)	0.0440 (3)
C3	0.80527 (19)	0.62986 (7)	0.24275 (14)	0.0512 (3)
H3A	0.7064	0.6474	0.1642	0.061*
C4	0.9099 (2)	0.58240 (7)	0.20867 (15)	0.0572 (4)
H4A	0.8805	0.5684	0.1067	0.069*
C5	1.0570 (2)	0.55487 (7)	0.32099 (16)	0.0571 (4)
C6	1.0959 (2)	0.57579 (8)	0.47215 (17)	0.0613 (4)
H6A	1.1935	0.5573	0.5504	0.074*
C7	0.9927 (2)	0.62340 (7)	0.50858 (14)	0.0552 (4)
H7A	1.0213	0.6366	0.6110	0.066*
C8	1.1734 (3)	0.50369 (9)	0.2821 (2)	0.0863 (5)
H8C	1.2149	0.4698	0.3627	0.104*
H8B	1.2721	0.5274	0.2727	0.104*
H8A	1.1072	0.4813	0.1861	0.104*
C9	0.53294 (17)	0.79984 (6)	0.35140 (12)	0.0433 (3)
C10	0.38966 (17)	0.78287 (7)	0.39137 (13)	0.0476 (3)
C11	0.29061 (19)	0.83671 (9)	0.41903 (14)	0.0579 (4)
C12	0.3352 (2)	0.90411 (9)	0.40209 (17)	0.0671 (4)
H12A	0.2703	0.9397	0.4221	0.081*
C13	0.4729 (2)	0.92024 (8)	0.35643 (15)	0.0635 (4)
H13A	0.4983	0.9660	0.3431	0.076*
C14	0.57237 (19)	0.86776 (7)	0.33078 (14)	0.0519 (3)
H14A	0.6655	0.8779	0.2998	0.062*
C15	0.3376 (2)	0.70931 (8)	0.39997 (17)	0.0644 (4)
H15C	0.2119	0.7050	0.3519	0.077*
H15B	0.3751	0.6955	0.5063	0.077*
H15A	0.3926	0.6804	0.3473	0.077*
C16	0.1334 (2)	0.82157 (11)	0.4618 (2)	0.0875 (6)
H16C	0.0944	0.8634	0.4942	0.105*
H16B	0.1659	0.7887	0.5448	0.105*
H16A	0.0398	0.8030	0.3738	0.105*
N1	0.64148 (14)	0.74732 (5)	0.32655 (10)	0.0464 (3)
H1A	0.6453	0.7433	0.2359	0.056*
O1	0.74010 (13)	0.70534 (5)	0.57153 (9)	0.0590 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0527 (8)	0.0490 (7)	0.0389 (6)	−0.0046 (6)	0.0246 (6)	−0.0015 (5)
C2	0.0533 (8)	0.0454 (7)	0.0388 (6)	−0.0039 (6)	0.0235 (6)	0.0006 (5)
C3	0.0606 (9)	0.0540 (8)	0.0424 (7)	0.0058 (7)	0.0229 (6)	−0.0014 (6)
C4	0.0755 (10)	0.0551 (8)	0.0476 (7)	0.0004 (7)	0.0306 (7)	−0.0053 (6)
C5	0.0686 (10)	0.0479 (8)	0.0666 (9)	0.0022 (7)	0.0387 (8)	0.0003 (6)
C6	0.0609 (9)	0.0601 (9)	0.0614 (8)	0.0103 (7)	0.0211 (7)	0.0072 (7)
C7	0.0664 (9)	0.0594 (9)	0.0411 (7)	0.0012 (7)	0.0215 (6)	0.0004 (6)
C8	0.0961 (13)	0.0766 (12)	0.1019 (13)	0.0218 (10)	0.0550 (11)	0.0016 (9)
C9	0.0481 (8)	0.0494 (8)	0.0337 (6)	−0.0015 (6)	0.0169 (5)	−0.0014 (5)
C10	0.0474 (8)	0.0599 (9)	0.0355 (6)	−0.0048 (6)	0.0154 (5)	−0.0020 (5)
C11	0.0486 (8)	0.0800 (11)	0.0440 (7)	0.0053 (8)	0.0159 (6)	−0.0056 (7)
C12	0.0661 (10)	0.0710 (11)	0.0602 (9)	0.0180 (8)	0.0186 (8)	−0.0097 (7)
C13	0.0714 (11)	0.0506 (8)	0.0600 (9)	0.0010 (8)	0.0145 (8)	−0.0013 (6)
C14	0.0550 (8)	0.0532 (8)	0.0473 (7)	−0.0053 (7)	0.0186 (6)	0.0015 (6)
C15	0.0630 (10)	0.0735 (10)	0.0602 (8)	−0.0178 (8)	0.0270 (7)	0.0017 (7)
C16	0.0647 (11)	0.1299 (16)	0.0789 (11)	0.0118 (11)	0.0395 (9)	−0.0020 (10)
N1	0.0596 (7)	0.0515 (6)	0.0367 (5)	0.0031 (5)	0.0277 (5)	0.0012 (4)
O1	0.0775 (7)	0.0704 (7)	0.0385 (5)	0.0099 (5)	0.0324 (5)	0.0019 (4)

Geometric parameters (Å, º) top

C1—O1	1.2327 (13)	C9—C10	1.3935 (18)
C1—N1	1.3542 (16)	C9—N1	1.4248 (16)
C1—C2	1.4873 (17)	C10—C11	1.402 (2)
C2—C7	1.3885 (19)	C10—C15	1.4991 (19)
C2—C3	1.3913 (17)	C11—C12	1.381 (2)
C3—C4	1.3711 (19)	C11—C16	1.509 (2)
C3—H3A	0.9300	C12—C13	1.379 (2)
C4—C5	1.376 (2)	C12—H12A	0.9300
C4—H4A	0.9300	C13—C14	1.378 (2)
C5—C6	1.385 (2)	C13—H13A	0.9300
C5—C8	1.509 (2)	C14—H14A	0.9300
C6—C7	1.375 (2)	C15—H15C	0.9600
C6—H6A	0.9300	C15—H15B	0.9600
C7—H7A	0.9300	C15—H15A	0.9600
C8—H8C	0.9600	C16—H16C	0.9600
C8—H8B	0.9600	C16—H16B	0.9600
C8—H8A	0.9600	C16—H16A	0.9600
C9—C14	1.3861 (18)	N1—H1A	0.8600

O1—C1—N1	122.69 (12)	C9—C10—C11	118.22 (12)
O1—C1—C2	120.95 (11)	C9—C10—C15	121.48 (13)
N1—C1—C2	116.36 (10)	C11—C10—C15	120.27 (13)
C7—C2—C3	118.04 (12)	C12—C11—C10	119.27 (14)
C7—C2—C1	118.87 (10)	C12—C11—C16	120.03 (15)
C3—C2—C1	123.07 (12)	C10—C11—C16	120.67 (15)
C4—C3—C2	120.36 (13)	C13—C12—C11	121.99 (14)
C4—C3—H3A	119.8	C13—C12—H12A	119.0
C2—C3—H3A	119.8	C11—C12—H12A	119.0
C3—C4—C5	121.90 (12)	C14—C13—C12	119.20 (14)
C3—C4—H4A	119.0	C14—C13—H13A	120.4
C5—C4—H4A	119.0	C12—C13—H13A	120.4
C4—C5—C6	117.77 (13)	C13—C14—C9	119.69 (14)
C4—C5—C8	121.57 (13)	C13—C14—H14A	120.2
C6—C5—C8	120.66 (14)	C9—C14—H14A	120.2
C7—C6—C5	121.17 (13)	C10—C15—H15C	109.5
C7—C6—H6A	119.4	C10—C15—H15B	109.5
C5—C6—H6A	119.4	H15C—C15—H15B	109.5
C6—C7—C2	120.73 (12)	C10—C15—H15A	109.5
C6—C7—H7A	119.6	H15C—C15—H15A	109.5
C2—C7—H7A	119.6	H15B—C15—H15A	109.5
C5—C8—H8C	109.5	C11—C16—H16C	109.5
C5—C8—H8B	109.5	C11—C16—H16B	109.5
H8C—C8—H8B	109.5	H16C—C16—H16B	109.5
C5—C8—H8A	109.5	C11—C16—H16A	109.5
H8C—C8—H8A	109.5	H16C—C16—H16A	109.5
H8B—C8—H8A	109.5	H16B—C16—H16A	109.5
C14—C9—C10	121.54 (12)	C1—N1—C9	123.11 (9)
C14—C9—N1	117.78 (11)	C1—N1—H1A	118.4
C10—C9—N1	120.67 (11)	C9—N1—H1A	118.4

O1—C1—C2—C7	−23.19 (18)	C14—C9—C10—C15	174.52 (11)
N1—C1—C2—C7	156.80 (12)	N1—C9—C10—C15	−3.88 (17)
O1—C1—C2—C3	155.62 (13)	C9—C10—C11—C12	1.61 (17)
N1—C1—C2—C3	−24.40 (18)	C15—C10—C11—C12	−176.44 (12)
C7—C2—C3—C4	−1.4 (2)	C9—C10—C11—C16	179.66 (12)
C1—C2—C3—C4	179.75 (12)	C15—C10—C11—C16	1.61 (18)
C2—C3—C4—C5	0.2 (2)	C10—C11—C12—C13	1.0 (2)
C3—C4—C5—C6	1.0 (2)	C16—C11—C12—C13	−177.06 (14)
C3—C4—C5—C8	−178.80 (14)	C11—C12—C13—C14	−1.8 (2)
C4—C5—C6—C7	−1.1 (2)	C12—C13—C14—C9	−0.10 (19)
C8—C5—C6—C7	178.74 (15)	C10—C9—C14—C13	2.77 (17)
C5—C6—C7—C2	−0.1 (2)	N1—C9—C14—C13	−178.78 (11)
C3—C2—C7—C6	1.4 (2)	O1—C1—N1—C9	0.50 (19)
C1—C2—C7—C6	−179.77 (13)	C2—C1—N1—C9	−179.49 (10)
C14—C9—C10—C11	−3.50 (17)	C14—C9—N1—C1	118.12 (13)
N1—C9—C10—C11	178.09 (10)	C10—C9—N1—C1	−63.42 (16)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1ⁱ	0.86	2.20	2.9256 (12)	143

Symmetry code: (i) x, −y+3/2, z−1/2.

Experimental details

Crystal data
Chemical formula	C₁₆H₁₇NO
M_r	239.31
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	8.1723 (3), 19.3923 (7), 9.3170 (3)
β (°)	111.781 (4)
V (Å³)	1371.14 (9)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.07
Crystal size (mm)	0.76 × 0.12 × 0.09

Data collection
Diffractometer	Oxford Xcalibur Ruby Gemini diffractometer
Absorption correction	Analytical [CrysAlis RED (Oxford Diffraction, 2009). Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by Clark & Reid (1995).]
T_min, T_max	0.989, 0.994
No. of measured, independent and observed [I > 2σ(I)] reflections	21529, 3806, 1925
R_int	0.030
(sin θ/λ)_max (Å⁻¹)	0.692

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.126, 0.93
No. of reflections	3806
No. of parameters	166
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.20, −0.18

Computer programs: CrysAlis CCD (Oxford Diffraction, 2009), CrysAlis RED (Oxford Diffraction, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg, 2002), enCIFer (Allen et al., 2004).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1ⁱ	0.86	2.20	2.9256 (12)	142.6

Symmetry code: (i) x, −y+3/2, z−1/2.

Acknowledgements

VZR thanks the University Grants Commission, Government of India, New Delhi, for the award of an RFSMS research fellowship. PH and JK thank the Grant Agencies for their financial support: the VEGA Grant Agency of the Slovak Ministry of Education (grant No. 1/0679/11), the Research and Development Agency (Slovakia) (grant No. APVV-0202-10), and the Structural Funds, Interreg IIIA, for financial support in purchasing the diffractometer.

References

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