N-(2,6-Dimethyl­phen­yl)-3-methyl­benzamide

Rodrigues, V.Z.; Tokarčík, M.; Gowda, B.T.; Kožíšek, J.

doi:10.1107/S1600536810011530

organic compounds

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ISSN: 2056-9890

Volume 66| Part 4| April 2010| Page o991

doi:10.1107/S1600536810011530

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N-(2,6-Dimethylphenyl)-3-methylbenzamide

Vinola Z. Rodrigues,^a Miroslav Tokarčík,^b B. Thimme Gowda ^a ^* and Jozef Kožíšek ^b

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

(Received 25 March 2010; accepted 26 March 2010; online 31 March 2010)

In the molecular structure of the title compound, C₁₆H₁₇NO, the N—H and C=O bonds are anti to each other. The two aromatic rings make a dihedral angle of 73.3 (1)°. In the crystal, intermolecular N—H⋯O hydrogen bonds connect the molecules into C(4) chains running along the c axis.

Related literature

For preparation of the title compound and related structures, see: Gowda et al. (2008a ,b , 2009 ); Bowes et al. (2003 ).

Experimental

Crystal data

C₁₆H₁₇NO
M_r = 239.31
Monoclinic, C c
a = 12.0715 (4) Å
b = 12.4966 (3) Å
c = 9.7027 (3) Å
β = 112.123 (4)°
V = 1355.92 (7) Å³
Z = 4
Mo Kα radiation
μ = 0.07 mm⁻¹
T = 295 K
0.55 × 0.30 × 0.18 mm

Data collection

Oxford Diffraction Xcalibur Ruby Gemini diffractometer
Absorption correction: analytical (CrysAlis PRO; Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.]$ ) T_min = 0.972, T_max = 0.989
11288 measured reflections
1371 independent reflections
1260 reflections with I > 2σ(I)
R_int = 0.030

Refinement

R[F² > 2σ(F²)] = 0.030
wR(F²) = 0.084
S = 1.08
1371 reflections
169 parameters
3 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.09 e Å⁻³
Δρ_min = −0.11 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1ⁱ	0.88 (2)	2.09 (2)	2.902 (2)	154 (2)
Symmetry code: (i) $[x, -y+1, z+{\script{1\over 2}}]$ .

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.]$ ); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ) and DIAMOND (Brandenburg, 2002 ); software used to prepare material for publication: SHELXL97, PLATON (Spek, 2009 ) and WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810011530/bt5228sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810011530/bt5228Isup2.hkl

checkCIF report

Comment top

As part of a study of the substituent effects on the crystal structures of benzanilides (Gowda et al., 2008a,b, 2009), in the present work, the structure of N-(2,6-dimethylphenyl)3-methylbenzamide (I) has been determined. In the structure, the conformations of the N—H and C=O bonds are anti to each other (Fig. 1), similar to those observed in N-(phenyl)3-methylbenzamide (II)(Gowda et al., 2008a), N-(2,6-dimethylphenyl)2-methylbenzamide (III) (Gowda et al., 2008b), N-(2,6-dichloromethylphenyl)- 3-methylbenzamide (IV)(Gowda et al., 2009) and the parent benzanilide (Bowes et al., 2003). Further, the conformation of the C=O bond in (I) is syn to the meta-methyl substituent in the benzoyl ring, similar to that observed in (III) and (IV), but contrary to the anti conformation observed between the C=O bond and the meta-methyl group in the benzoyl ring of (II).

The two aromatic rings make a dihedral angle of 73.3 (1) °. The amide group –NH–C(=O)– is twisted by 81.0 (1)° and 25.8 (2)° out of the planes of the 2,6-dimethylphenyl and 3-methylphenyl rings, respectively. In the crystal, intermolecular N–H···O hydrogen bonds (Table 1) connect the molecules into chains running along the c-axis (Fig. 2).

Related literature top

For preparation of the title compound, see: Gowda et al. (2008a,b). For related structures, see: Bowes et al. (2003); Gowda et al. (2008a,b, 2009).

Experimental top

The title compound was prepared according to the literature method (Gowda et al., 2008a,b). The purity of the compound was checked by determining its melting point. It was characterized by recording its infrared and NMR spectra. Single crystals of the title compound used in X-ray diffraction studies were obtained from a slow evaporation of its ethanolic solution at room temperature.

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2009); cell refinement: CrysAlis PRO (Oxford Diffraction, 2009); data reduction: CrysAlis PRO (Oxford Diffraction, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2002); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009) and WinGX (Farrugia, 1999).

Figures top

	Fig. 1. Molecular structure of (I) showing the atom labelling scheme. Displacement ellipsoids are drawn at the 30% probability level and H atoms are represented as small spheres of arbitrary radii.
	Fig. 2. Part of crystal structure of (I) showing molecular chains running along the c-axis. Hydrogen bonds are shown as dashed lines. H atoms not involved in hydrogen bonding were omitted. Symmetry code:(i) x, -y+1, z+1/2.

N-(2,6-Dimethylphenyl)-3-methylbenzamide top

Crystal data top

C₁₆H₁₇NO	F(000) = 512
M_r = 239.31	D_x = 1.172 Mg m⁻³
Monoclinic, Cc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2yc	Cell parameters from 6791 reflections
a = 12.0715 (4) Å	θ = 2.3–29.5°
b = 12.4966 (3) Å	µ = 0.07 mm⁻¹
c = 9.7027 (3) Å	T = 295 K
β = 112.123 (4)°	Block, colourless
V = 1355.92 (7) Å³	0.55 × 0.30 × 0.18 mm
Z = 4

Data collection top

Oxford Diffraction Xcalibur Ruby Gemini diffractometer	1371 independent reflections
Graphite monochromator	1260 reflections with I > 2σ(I)
Detector resolution: 10.434 pixels mm^-1	R_int = 0.030
ω scans	θ_max = 26.2°, θ_min = 2.4°
Absorption correction: analytical (CrysAlis PRO; Oxford Diffraction, 2009)	h = −14→14
T_min = 0.972, T_max = 0.989	k = −15→15
11288 measured reflections	l = −12→12

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)] = 0.030	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.084	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	w = 1/[σ²(F_o²) + (0.0513P)² + 0.1381P] where P = (F_o² + 2F_c²)/3
1371 reflections	(Δ/σ)_max < 0.001
169 parameters	Δρ_max = 0.09 e Å⁻³
3 restraints	Δρ_min = −0.11 e Å⁻³

Crystal data top

C₁₆H₁₇NO	V = 1355.92 (7) Å³
M_r = 239.31	Z = 4
Monoclinic, Cc	Mo Kα radiation
a = 12.0715 (4) Å	µ = 0.07 mm⁻¹
b = 12.4966 (3) Å	T = 295 K
c = 9.7027 (3) Å	0.55 × 0.30 × 0.18 mm
β = 112.123 (4)°

Data collection top

Oxford Diffraction Xcalibur Ruby Gemini diffractometer	1371 independent reflections
Absorption correction: analytical (CrysAlis PRO; Oxford Diffraction, 2009)	1260 reflections with I > 2σ(I)
T_min = 0.972, T_max = 0.989	R_int = 0.030
11288 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.030	3 restraints
wR(F²) = 0.084	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	Δρ_max = 0.09 e Å⁻³
1371 reflections	Δρ_min = −0.11 e Å⁻³
169 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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	0.78435 (17)	0.48438 (15)	0.42193 (19)	0.0400 (4)
C2	0.67477 (16)	0.55392 (15)	0.3679 (2)	0.0411 (4)
C3	0.58869 (18)	0.53174 (18)	0.2278 (2)	0.0482 (5)
H3	0.6004	0.4745	0.1736	0.058*
C4	0.48627 (19)	0.5928 (2)	0.1676 (2)	0.0558 (5)
C5	0.4723 (2)	0.6792 (2)	0.2490 (3)	0.0622 (6)
H5	0.4047	0.7221	0.2095	0.075*
C6	0.5568 (2)	0.7029 (2)	0.3876 (3)	0.0602 (5)
H6	0.5457	0.7612	0.4407	0.072*
C7	0.65776 (19)	0.64009 (17)	0.4474 (2)	0.0486 (5)
H7	0.7144	0.6556	0.5413	0.058*
C8	0.95159 (17)	0.41695 (16)	0.63591 (19)	0.0422 (4)
C9	1.05908 (18)	0.46294 (17)	0.6440 (2)	0.0494 (5)
C10	1.1631 (2)	0.4041 (2)	0.7137 (3)	0.0621 (6)
H10	1.236	0.4327	0.7202	0.074*
C11	1.1606 (2)	0.3050 (2)	0.7730 (3)	0.0677 (7)
H11	1.2314	0.2674	0.8199	0.081*
C12	1.0537 (3)	0.2613 (2)	0.7630 (3)	0.0631 (6)
H12	1.0529	0.1939	0.8032	0.076*
C13	0.9464 (2)	0.31583 (16)	0.6939 (2)	0.0496 (5)
C14	0.3930 (3)	0.5643 (3)	0.0162 (3)	0.0890 (9)
H14A	0.3383	0.6229	−0.0201	0.134*
H14B	0.35	0.5018	0.0251	0.134*
H14C	0.4318	0.5502	−0.052	0.134*
C15	1.0634 (3)	0.5708 (2)	0.5791 (4)	0.0742 (7)
H15A	1.1447	0.5955	0.6142	0.111*
H15B	1.0159	0.6203	0.609	0.111*
H15C	1.0326	0.5658	0.4726	0.111*
C16	0.8297 (3)	0.2675 (2)	0.6825 (3)	0.0724 (7)
H16A	0.8367	0.191	0.687	0.109*
H16B	0.7684	0.2881	0.5898	0.109*
H16C	0.8091	0.2926	0.7633	0.109*
N1	0.84288 (14)	0.47696 (14)	0.56895 (16)	0.0447 (4)
H1N	0.813 (2)	0.5097 (19)	0.627 (3)	0.054*
O1	0.81747 (13)	0.43660 (12)	0.33310 (16)	0.0518 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0423 (9)	0.0448 (9)	0.0324 (9)	−0.0060 (8)	0.0137 (7)	−0.0005 (8)
C2	0.0397 (9)	0.0481 (10)	0.0340 (9)	−0.0046 (8)	0.0120 (7)	0.0050 (8)
C3	0.0482 (11)	0.0587 (12)	0.0359 (10)	−0.0064 (9)	0.0138 (9)	0.0009 (9)
C4	0.0458 (11)	0.0759 (14)	0.0402 (11)	−0.0028 (10)	0.0099 (9)	0.0115 (10)
C5	0.0512 (12)	0.0728 (15)	0.0604 (14)	0.0135 (11)	0.0185 (11)	0.0195 (12)
C6	0.0631 (13)	0.0576 (12)	0.0598 (14)	0.0085 (11)	0.0229 (11)	0.0032 (10)
C7	0.0487 (10)	0.0525 (11)	0.0408 (10)	−0.0012 (9)	0.0125 (8)	−0.0009 (9)
C8	0.0453 (10)	0.0484 (10)	0.0304 (8)	0.0037 (8)	0.0114 (8)	−0.0028 (7)
C9	0.0473 (11)	0.0570 (12)	0.0418 (11)	−0.0009 (9)	0.0146 (9)	−0.0057 (9)
C10	0.0456 (12)	0.0837 (16)	0.0536 (13)	0.0025 (11)	0.0149 (10)	−0.0075 (12)
C11	0.0613 (15)	0.0842 (18)	0.0515 (12)	0.0281 (13)	0.0141 (11)	0.0041 (12)
C12	0.0868 (17)	0.0527 (13)	0.0523 (13)	0.0181 (12)	0.0291 (12)	0.0080 (10)
C13	0.0605 (11)	0.0510 (11)	0.0376 (9)	0.0016 (10)	0.0187 (9)	−0.0024 (8)
C14	0.0626 (16)	0.133 (3)	0.0529 (15)	0.0034 (17)	0.0006 (13)	0.0060 (16)
C15	0.0653 (15)	0.0700 (15)	0.0866 (19)	−0.0104 (13)	0.0280 (14)	0.0054 (14)
C16	0.0841 (17)	0.0659 (15)	0.0730 (16)	−0.0121 (13)	0.0361 (14)	0.0059 (13)
N1	0.0446 (9)	0.0578 (10)	0.0314 (8)	0.0074 (7)	0.0141 (7)	0.0007 (7)
O1	0.0549 (8)	0.0638 (9)	0.0357 (7)	0.0053 (7)	0.0161 (6)	−0.0030 (6)

Geometric parameters (Å, º) top

C1—O1	1.232 (2)	C9—C15	1.496 (3)
C1—N1	1.336 (2)	C10—C11	1.371 (4)
C1—C2	1.502 (3)	C10—H10	0.93
C2—C7	1.385 (3)	C11—C12	1.370 (4)
C2—C3	1.392 (3)	C11—H11	0.93
C3—C4	1.381 (3)	C12—C13	1.392 (3)
C3—H3	0.93	C12—H12	0.93
C4—C5	1.386 (4)	C13—C16	1.498 (4)
C4—C14	1.518 (3)	C14—H14A	0.96
C5—C6	1.380 (3)	C14—H14B	0.96
C5—H5	0.93	C14—H14C	0.96
C6—C7	1.381 (3)	C15—H15A	0.96
C6—H6	0.93	C15—H15B	0.96
C7—H7	0.93	C15—H15C	0.96
C8—C13	1.394 (3)	C16—H16A	0.96
C8—C9	1.394 (3)	C16—H16B	0.96
C8—N1	1.437 (3)	C16—H16C	0.96
C9—C10	1.391 (3)	N1—H1N	0.875 (17)

O1—C1—N1	122.20 (18)	C12—C11—C10	119.9 (2)
O1—C1—C2	120.72 (16)	C12—C11—H11	120
N1—C1—C2	117.08 (16)	C10—C11—H11	120
C7—C2—C3	119.08 (17)	C11—C12—C13	121.3 (2)
C7—C2—C1	123.44 (16)	C11—C12—H12	119.3
C3—C2—C1	117.45 (17)	C13—C12—H12	119.3
C4—C3—C2	121.5 (2)	C12—C13—C8	117.6 (2)
C4—C3—H3	119.2	C12—C13—C16	121.1 (2)
C2—C3—H3	119.2	C8—C13—C16	121.3 (2)
C3—C4—C5	118.1 (2)	C4—C14—H14A	109.5
C3—C4—C14	120.0 (2)	C4—C14—H14B	109.5
C5—C4—C14	121.9 (2)	H14A—C14—H14B	109.5
C6—C5—C4	121.3 (2)	C4—C14—H14C	109.5
C6—C5—H5	119.4	H14A—C14—H14C	109.5
C4—C5—H5	119.4	H14B—C14—H14C	109.5
C5—C6—C7	119.9 (2)	C9—C15—H15A	109.5
C5—C6—H6	120	C9—C15—H15B	109.5
C7—C6—H6	120	H15A—C15—H15B	109.5
C6—C7—C2	120.05 (19)	C9—C15—H15C	109.5
C6—C7—H7	120	H15A—C15—H15C	109.5
C2—C7—H7	120	H15B—C15—H15C	109.5
C13—C8—C9	122.22 (18)	C13—C16—H16A	109.5
C13—C8—N1	118.92 (18)	C13—C16—H16B	109.5
C9—C8—N1	118.84 (18)	H16A—C16—H16B	109.5
C10—C9—C8	117.4 (2)	C13—C16—H16C	109.5
C10—C9—C15	120.8 (2)	H16A—C16—H16C	109.5
C8—C9—C15	121.80 (19)	H16B—C16—H16C	109.5
C11—C10—C9	121.6 (2)	C1—N1—C8	123.02 (16)
C11—C10—H10	119.2	C1—N1—H1N	118.3 (17)
C9—C10—H10	119.2	C8—N1—H1N	118.7 (17)

O1—C1—C2—C7	−153.25 (19)	C13—C8—C9—C15	179.0 (2)
N1—C1—C2—C7	26.9 (3)	N1—C8—C9—C15	−2.6 (3)
O1—C1—C2—C3	24.4 (3)	C8—C9—C10—C11	−0.3 (3)
N1—C1—C2—C3	−155.44 (17)	C15—C9—C10—C11	−179.7 (2)
C7—C2—C3—C4	−0.8 (3)	C9—C10—C11—C12	0.6 (4)
C1—C2—C3—C4	−178.60 (18)	C10—C11—C12—C13	−0.2 (3)
C2—C3—C4—C5	1.6 (3)	C11—C12—C13—C8	−0.4 (3)
C2—C3—C4—C14	−178.4 (2)	C11—C12—C13—C16	179.6 (2)
C3—C4—C5—C6	−1.2 (3)	C9—C8—C13—C12	0.7 (3)
C14—C4—C5—C6	178.8 (3)	N1—C8—C13—C12	−177.66 (18)
C4—C5—C6—C7	0.1 (3)	C9—C8—C13—C16	−179.3 (2)
C5—C6—C7—C2	0.6 (3)	N1—C8—C13—C16	2.3 (3)
C3—C2—C7—C6	−0.3 (3)	O1—C1—N1—C8	2.8 (3)
C1—C2—C7—C6	177.36 (19)	C2—C1—N1—C8	−177.37 (17)
C13—C8—C9—C10	−0.4 (3)	C13—C8—N1—C1	−101.4 (2)
N1—C8—C9—C10	177.99 (18)	C9—C8—N1—C1	80.2 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1ⁱ	0.88 (2)	2.09 (2)	2.902 (2)	154 (2)

Symmetry code: (i) x, −y+1, z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₆H₁₇NO
M_r	239.31
Crystal system, space group	Monoclinic, Cc
Temperature (K)	295
a, b, c (Å)	12.0715 (4), 12.4966 (3), 9.7027 (3)
β (°)	112.123 (4)
V (Å³)	1355.92 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.07
Crystal size (mm)	0.55 × 0.30 × 0.18

Data collection
Diffractometer	Oxford Diffraction Xcalibur Ruby Gemini diffractometer
Absorption correction	Analytical (CrysAlis PRO; Oxford Diffraction, 2009)
T_min, T_max	0.972, 0.989
No. of measured, independent and observed [I > 2σ(I)] reflections	11288, 1371, 1260
R_int	0.030
(sin θ/λ)_max (Å⁻¹)	0.622

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.030, 0.084, 1.08
No. of reflections	1371
No. of parameters	169
No. of restraints	3
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.09, −0.11

Computer programs: CrysAlis PRO (Oxford Diffraction, 2009), SHELXS97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2002), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009) and WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1ⁱ	0.875 (17)	2.092 (19)	2.902 (2)	154 (2)

Symmetry code: (i) x, −y+1, z+1/2.

Acknowledgements

MT and JK thank the Grant Agency of the Slovak Republic (VEGA 1/0817/08) and the Structural Funds, Interreg IIIA, for financial support in purchasing the diffractometer. VZR thanks the University Grants Commission, Government of India, New Delhi, for the award of a research fellowship.

References

Bowes, K. F., Glidewell, C., Low, J. N., Skakle, J. M. S. & Wardell, J. L. (2003). Acta Cryst. C59, o1–o3. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Brandenburg, K. (2002). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. CrossRef CAS IUCr Journals Google Scholar
Gowda, B. T., Foro, S., Sowmya, B. P. & Fuess, H. (2008a). Acta Cryst. E64, o770. Web of Science CSD CrossRef IUCr Journals Google Scholar
Gowda, B. T., Foro, S., Sowmya, B. P. & Fuess, H. (2008b). Acta Cryst. E64, o1605. Web of Science CSD CrossRef IUCr Journals Google Scholar
Gowda, B. T., Tokarčík, M., Kožíšek, J., Rodrigues, V. Z. & Fuess, H. (2009). Acta Cryst. E65, o2713. Web of Science CrossRef IUCr Journals Google Scholar
Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar