2-Methyl-N-phenyl­benzamide

Gowda, B.T.; Foro, S.; Sowmya, B.P.; Fuess, H.

doi:10.1107/S1600536807068821

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 64| Part 2| February 2008| Page o383

doi:10.1107/S1600536807068821

Open

access

2-Methyl-N-phenylbenzamide

B. Thimme Gowda,^a ^* Sabine Foro,^b B. P. Sowmya ^a and Hartmut Fuess ^b

^aDepartment of Chemistry, Mangalore University, Mangalagangotri 574 199, Mangalore, India, and ^bInstitute of Materials Science, Darmstadt University of Technology, Petersenstrasse 23, D-64287 Darmstadt, Germany
^*Correspondence e-mail: gowdabt@yahoo.com

(Received 28 December 2007; accepted 31 December 2007; online 9 January 2008)

In the structure of the title compound (NP2MBA), C₁₄H₁₃NO, the conformation of the C—O bond is syn to the ortho-methyl substituent in the benzoyl phenyl ring, while the N—H bond is anti to the ortho-methyl substituent. The structure of NP2MBA closely resembles that of 2-chloro-N-phenylbenzamide, with similar bond parameters. The dihedral angle between the phenyl and benzoyl rings is 88.05 (5)°. Molecules are linked into a chain through N—H⋯O hydrogen bonding.

Related literature

For related literature, see: Gowda et al. (2003 , 2007 , 2008 ).

Experimental

Crystal data

C₁₄H₁₃NO
M_r = 211.25
Orthorhombic, P b c a
a = 14.404 (1) Å
b = 8.6824 (6) Å
c = 18.710 (1) Å
V = 2339.9 (3) Å³
Z = 8
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 100 (2) K
0.40 × 0.20 × 0.16 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with Sapphire CCD detector
Absorption correction: multi-scan (SCALE3 ABSPACK; Oxford Diffraction, 2007 $[Oxford Diffraction (2007). CrysAlis RED. Version 1.171.32.5. Oxford Diffraction Ltd. Abingdon, Oxfordshire, England.]$ ) T_min = 0.970, T_max = 0.981
11005 measured reflections
2387 independent reflections
1686 reflections with I > 2σ(I)
R_int = 0.029

Refinement

R[F² > 2σ(F²)] = 0.038
wR(F²) = 0.115
S = 1.05
2387 reflections
149 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1ⁱ	0.878 (17)	2.012 (18)	2.8751 (16)	167.7 (15)
Symmetry code: (i) $[-x+{\script{3\over 2}}, y+{\script{1\over 2}}, z]$ .

Data collection: CrysAlis CCD (Oxford Diffraction, 2004 $[Oxford Diffraction (2004). CrysAlis CCD. Version 1.171.26. Oxford Diffraction Ltd. Abingdon, Oxfordshire, England.]$ ); cell refinement: CrysAlis RED (Oxford Diffraction, 2007 $[Oxford Diffraction (2007). CrysAlis RED. Version 1.171.32.5. Oxford Diffraction Ltd. Abingdon, Oxfordshire, England.]$ ); 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: SHELXS97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536807068821/dn2308sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536807068821/dn2308Isup2.hkl

checkCIF report

Comment top

As part of a study of the substituent effects on the structures of benzanilides, in the present work, the structure of 2-methyl-N-(phenyl)benzamide (NP2MBA) has been determined (Gowda, et al., 2003; 2007; 2008). In the structure of NP2MBA,(Fig. 1), the conformation of the C—O bond is syn to the ortho-methyl substituent in the benzoyl phenyl ring, while the N—H bond is anti to the ortho-methyl substituent. The bond parameters in NP2MBA are similar to those in 2-chloro-N-(phenyl)-benzamide (Gowda, et al.,2003), 2-chloro-N-(2-chlorophenyl)-benzamide (Gowda, et al.,2007), N-(4-methylphenyl)-benzamide (Gowda, et al.,2008) and other benzanilides. The dihedral angle between the phenyl and benzoyl rings in NP2MBA is 88.05 (5)°. The packing diagram of NP2MBA molecules showing the hydrogen bonds N1—H1N···O1 (Table 1) involved in the formation of molecular chain is shown in Fig. 2.

Related literature top

For related literature, see: Gowda et al. (2003, 2007, 2008).

Experimental top

The title compound was prepared according to the literature method (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. Single crystals of the title compound were obtained from an ethanolic solution and used for X-ray diffraction studies at room temperature.

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2004); cell refinement: CrysAlis RED (Oxford Diffraction, 2007); data reduction: CrysAlis RED (Oxford Diffraction, 2007); 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: SHELXS97 (Sheldrick, 2008).

Figures top

	Fig. 1. Molecular structure of the title compound, showing the atom labeling scheme. The displacement ellipsoids are drawn at the 50% probability level. H atoms are represented as small spheres of arbitrary radii.
	Fig. 2. Molecular packing of the title compound with hydrogen bonding shown as dashed lines.H atoms not involved in hydrogen bondings have been omitted for clarity. [Symmetry code: (i) 3/2 - x, 1/2 + y, z]

2-Methyl-N-phenylbenzamide top

Crystal data top

C₁₄H₁₃NO	F(000) = 896
M_r = 211.25	D_x = 1.199 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 3291 reflections
a = 14.404 (1) Å	θ = 1.5–26.9°
b = 8.6824 (6) Å	µ = 0.08 mm⁻¹
c = 18.710 (1) Å	T = 100 K
V = 2339.9 (3) Å³	Rod, colourless
Z = 8	0.40 × 0.20 × 0.16 mm

Data collection top

Oxford Diffraction Xcalibur diffractometer with Sapphire CCD Detector	2387 independent reflections
Radiation source: fine-focus sealed tube	1686 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.029
Rotation method data acquisition using ω and ϕ scans.	θ_max = 26.4°, θ_min = 2.6°
Absorption correction: multi-scan (SCALE3 ABSPACK; Oxford Diffraction, 2007)	h = −17→17
T_min = 0.970, T_max = 0.981	k = −10→10
11005 measured reflections	l = −23→23

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.115	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ²(F_o²) + (0.0589P)² + 0.6762P] where P = (F_o² + 2F_c²)/3
2387 reflections	(Δ/σ)_max = 0.007
149 parameters	Δρ_max = 0.24 e Å⁻³
0 restraints	Δρ_min = −0.21 e Å⁻³

Crystal data top

C₁₄H₁₃NO	V = 2339.9 (3) Å³
M_r = 211.25	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 14.404 (1) Å	µ = 0.08 mm⁻¹
b = 8.6824 (6) Å	T = 100 K
c = 18.710 (1) Å	0.40 × 0.20 × 0.16 mm

Data collection top

Oxford Diffraction Xcalibur diffractometer with Sapphire CCD Detector	2387 independent reflections
Absorption correction: multi-scan (SCALE3 ABSPACK; Oxford Diffraction, 2007)	1686 reflections with I > 2σ(I)
T_min = 0.970, T_max = 0.981	R_int = 0.029
11005 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.038	0 restraints
wR(F²) = 0.115	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	Δρ_max = 0.24 e Å⁻³
2387 reflections	Δρ_min = −0.21 e Å⁻³
149 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	0.69394 (10)	0.28490 (16)	0.53783 (8)	0.0226 (3)
C2	0.60165 (11)	0.32710 (18)	0.52773 (9)	0.0298 (4)
H2	0.5740	0.4029	0.5575	0.036*
C3	0.55046 (12)	0.2578 (2)	0.47398 (10)	0.0395 (5)
H3	0.4876	0.2869	0.4667	0.047*
C4	0.59039 (14)	0.1463 (2)	0.43075 (10)	0.0421 (5)
H4	0.5544	0.0966	0.3950	0.051*
C5	0.68238 (13)	0.1079 (2)	0.43987 (9)	0.0360 (4)
H5	0.7102	0.0334	0.4094	0.043*
C6	0.73475 (11)	0.17696 (18)	0.49311 (8)	0.0276 (4)
H6	0.7983	0.1505	0.4990	0.033*
C7	0.80898 (9)	0.28653 (16)	0.63583 (7)	0.0197 (3)
C8	0.85208 (9)	0.38985 (16)	0.69023 (8)	0.0203 (3)
C9	0.85849 (9)	0.34624 (16)	0.76232 (8)	0.0231 (3)
C10	0.90322 (10)	0.44704 (19)	0.80890 (9)	0.0284 (4)
H10	0.9075	0.4210	0.8581	0.034*
C11	0.94171 (11)	0.58472 (19)	0.78533 (9)	0.0323 (4)
H11	0.9735	0.6498	0.8180	0.039*
C12	0.93373 (11)	0.62687 (18)	0.71470 (9)	0.0310 (4)
H12	0.9590	0.7218	0.6986	0.037*
C13	0.88876 (10)	0.53029 (16)	0.66721 (9)	0.0248 (4)
H13	0.8828	0.5597	0.6185	0.030*
C14	0.81853 (11)	0.19677 (19)	0.78942 (8)	0.0311 (4)
H14A	0.8571	0.1108	0.7730	0.037*
H14B	0.7552	0.1842	0.7711	0.037*
H14C	0.8172	0.1981	0.8418	0.037*
N1	0.74373 (8)	0.35464 (14)	0.59463 (7)	0.0220 (3)
H1N	0.7283 (11)	0.448 (2)	0.6078 (9)	0.026*
O1	0.83366 (7)	0.15084 (11)	0.62885 (6)	0.0245 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0295 (8)	0.0138 (7)	0.0244 (7)	−0.0039 (6)	−0.0054 (6)	0.0032 (6)
C2	0.0308 (8)	0.0223 (8)	0.0362 (9)	−0.0009 (7)	−0.0051 (7)	0.0040 (7)
C3	0.0335 (9)	0.0373 (10)	0.0477 (10)	−0.0048 (8)	−0.0176 (8)	0.0095 (9)
C4	0.0563 (12)	0.0291 (9)	0.0410 (10)	−0.0117 (9)	−0.0223 (9)	0.0006 (9)
C5	0.0541 (11)	0.0221 (8)	0.0316 (9)	−0.0039 (8)	−0.0079 (8)	−0.0018 (8)
C6	0.0348 (8)	0.0204 (8)	0.0276 (8)	−0.0022 (7)	−0.0039 (7)	0.0007 (7)
C7	0.0189 (7)	0.0154 (7)	0.0248 (7)	−0.0018 (5)	0.0013 (6)	0.0015 (6)
C8	0.0172 (7)	0.0154 (7)	0.0284 (8)	0.0023 (5)	−0.0008 (6)	−0.0020 (6)
C9	0.0183 (7)	0.0217 (7)	0.0294 (8)	0.0040 (6)	−0.0005 (6)	−0.0019 (7)
C10	0.0249 (8)	0.0316 (9)	0.0287 (8)	0.0065 (7)	−0.0055 (7)	−0.0063 (8)
C11	0.0246 (8)	0.0273 (8)	0.0452 (10)	0.0000 (7)	−0.0082 (7)	−0.0151 (8)
C12	0.0263 (8)	0.0190 (8)	0.0478 (10)	−0.0038 (6)	−0.0030 (7)	−0.0031 (8)
C13	0.0235 (7)	0.0176 (7)	0.0333 (8)	0.0001 (6)	−0.0013 (6)	0.0009 (7)
C14	0.0336 (9)	0.0299 (9)	0.0298 (8)	−0.0022 (7)	−0.0004 (7)	0.0052 (8)
N1	0.0261 (6)	0.0126 (6)	0.0273 (7)	0.0019 (5)	−0.0033 (6)	−0.0017 (6)
O1	0.0274 (5)	0.0124 (5)	0.0336 (6)	0.0014 (4)	−0.0033 (5)	−0.0018 (5)

Geometric parameters (Å, º) top

C1—C6	1.387 (2)	C8—C13	1.397 (2)
C1—C2	1.392 (2)	C8—C9	1.404 (2)
C1—N1	1.4180 (18)	C9—C10	1.393 (2)
C2—C3	1.385 (2)	C9—C14	1.507 (2)
C2—H2	0.9500	C10—C11	1.390 (2)
C3—C4	1.387 (3)	C10—H10	0.9500
C3—H3	0.9500	C11—C12	1.376 (2)
C4—C5	1.377 (3)	C11—H11	0.9500
C4—H4	0.9500	C12—C13	1.383 (2)
C5—C6	1.386 (2)	C12—H12	0.9500
C5—H5	0.9500	C13—H13	0.9500
C6—H6	0.9500	C14—H14A	0.9800
C7—O1	1.2375 (17)	C14—H14B	0.9800
C7—N1	1.3516 (18)	C14—H14C	0.9800
C7—C8	1.492 (2)	N1—H1N	0.878 (17)

C6—C1—C2	120.05 (14)	C10—C9—C8	117.51 (14)
C6—C1—N1	121.76 (13)	C10—C9—C14	120.47 (14)
C2—C1—N1	118.19 (13)	C8—C9—C14	122.01 (13)
C3—C2—C1	119.53 (16)	C11—C10—C9	121.78 (15)
C3—C2—H2	120.2	C11—C10—H10	119.1
C1—C2—H2	120.2	C9—C10—H10	119.1
C2—C3—C4	120.41 (16)	C12—C11—C10	120.01 (15)
C2—C3—H3	119.8	C12—C11—H11	120.0
C4—C3—H3	119.8	C10—C11—H11	120.0
C5—C4—C3	119.73 (16)	C11—C12—C13	119.66 (15)
C5—C4—H4	120.1	C11—C12—H12	120.2
C3—C4—H4	120.1	C13—C12—H12	120.2
C4—C5—C6	120.53 (17)	C12—C13—C8	120.56 (15)
C4—C5—H5	119.7	C12—C13—H13	119.7
C6—C5—H5	119.7	C8—C13—H13	119.7
C5—C6—C1	119.69 (15)	C9—C14—H14A	109.5
C5—C6—H6	120.2	C9—C14—H14B	109.5
C1—C6—H6	120.2	H14A—C14—H14B	109.5
O1—C7—N1	123.79 (13)	C9—C14—H14C	109.5
O1—C7—C8	121.65 (12)	H14A—C14—H14C	109.5
N1—C7—C8	114.53 (12)	H14B—C14—H14C	109.5
C13—C8—C9	120.44 (14)	C7—N1—C1	126.32 (12)
C13—C8—C7	118.16 (13)	C7—N1—H1N	114.9 (11)
C9—C8—C7	121.37 (13)	C1—N1—H1N	118.5 (11)

C6—C1—C2—C3	1.6 (2)	C13—C8—C9—C14	179.07 (13)
N1—C1—C2—C3	−178.20 (14)	C7—C8—C9—C14	−2.9 (2)
C1—C2—C3—C4	0.5 (3)	C8—C9—C10—C11	−1.1 (2)
C2—C3—C4—C5	−2.1 (3)	C14—C9—C10—C11	179.21 (14)
C3—C4—C5—C6	1.7 (3)	C9—C10—C11—C12	2.0 (2)
C4—C5—C6—C1	0.4 (2)	C10—C11—C12—C13	−1.2 (2)
C2—C1—C6—C5	−2.0 (2)	C11—C12—C13—C8	−0.5 (2)
N1—C1—C6—C5	177.73 (14)	C9—C8—C13—C12	1.5 (2)
O1—C7—C8—C13	126.10 (15)	C7—C8—C13—C12	−176.65 (13)
N1—C7—C8—C13	−52.29 (17)	O1—C7—N1—C1	−0.2 (2)
O1—C7—C8—C9	−51.99 (19)	C8—C7—N1—C1	178.11 (13)
N1—C7—C8—C9	129.62 (14)	C6—C1—N1—C7	−35.5 (2)
C13—C8—C9—C10	−0.7 (2)	C2—C1—N1—C7	144.32 (15)
C7—C8—C9—C10	177.40 (13)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1ⁱ	0.878 (17)	2.012 (18)	2.8751 (16)	167.7 (15)

Symmetry code: (i) −x+3/2, y+1/2, z.

Experimental details

Crystal data
Chemical formula	C₁₄H₁₃NO
M_r	211.25
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	100
a, b, c (Å)	14.404 (1), 8.6824 (6), 18.710 (1)
V (Å³)	2339.9 (3)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.40 × 0.20 × 0.16

Data collection
Diffractometer	Oxford Diffraction Xcalibur diffractometer with Sapphire CCD Detector
Absorption correction	Multi-scan (SCALE3 ABSPACK; Oxford Diffraction, 2007)
T_min, T_max	0.970, 0.981
No. of measured, independent and observed [I > 2σ(I)] reflections	11005, 2387, 1686
R_int	0.029
(sin θ/λ)_max (Å⁻¹)	0.625

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.038, 0.115, 1.05
No. of reflections	2387
No. of parameters	149
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.24, −0.21

Computer programs: CrysAlis CCD (Oxford Diffraction, 2004), CrysAlis RED (Oxford Diffraction, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1ⁱ	0.878 (17)	2.012 (18)	2.8751 (16)	167.7 (15)

Symmetry code: (i) −x+3/2, y+1/2, z.

Acknowledgements

BTG thanks the Alexander von Humboldt Foundation, Bonn, Germany, for extensions of his research fellowship.

References

Gowda, B. T., Foro, S., Sowmya, B. P. & Fuess, H. (2007). Acta Cryst. E63, o3789. Web of Science CSD CrossRef IUCr Journals Google Scholar
Gowda, B. T., Jyothi, K., Paulus, H. & Fuess, H. (2003). Z. Naturforsch. Teil A, 58, 225–230. CAS Google Scholar
Gowda, B. T., Tokarčík, M., Kožíšek, J. & Sowmya, B. P. (2008). Acta Cryst. E64, o83. Web of Science CSD CrossRef IUCr Journals Google Scholar
Oxford Diffraction (2004). CrysAlis CCD. Version 1.171.26. Oxford Diffraction Ltd. Abingdon, Oxfordshire, England. Google Scholar
Oxford Diffraction (2007). CrysAlis RED. Version 1.171.32.5. Oxford Diffraction Ltd. Abingdon, 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. (2003). PLATON. J. Appl. Cryst. 36, 7–13. Web of Science CrossRef CAS IUCr Journals Google Scholar