N-(4-Methyl­phen­yl)benzamide

Abstract

The structure of the title compound, C₁₄H₁₃NO, resembles those of N-(2-chloro­phen­yl)benzamide, 2-chloro-N-phenyl­benzamide, N-(2,3-dichloro­phen­yl)benzamide, N-(3,4-dichloro­phen­yl)benzamide and 2-chloro-N-(2-chloro­phen­yl)benzamide with similar bond parameters. The benzene and methylphenyl rings have a dihedral angle of 63.41 (5)°, while the amide group makes a dihedral angle of 20.5 (1)° with the benzene ring. The mol­ecules are linked into chains in the b-axis direction by N—H⋯O hydrogen bonds.

Related literature

For related literature, see: Gowda et al. (2003 ▶, 2007a ▶,b ▶,c ▶); Gowda, Foro et al. (2007 ▶).

Experimental

Crystal data

• C₁₄H₁₃NO

• M _r = 211.25

• Orthorhombic,

• a = 9.1117 (3) Å

• b = 9.8336 (2) Å

• c = 26.0616 (10) Å

• V = 2335.14 (13) ų

• Z = 8

• Mo Kα radiation

• μ = 0.08 mm⁻¹

• T = 295 (2) K

• 0.26 × 0.07 × 0.06 mm

Data collection

• Oxford Diffraction Xcalibur diffractometer

• Absorption correction: none

• 21626 measured reflections

• 2276 independent reflections

• 1060 reflections with I > 2σ(I)

• R _int = 0.078

Refinement

• R[F ² > 2σ(F ²)] = 0.035

• wR(F ²) = 0.084

• S = 0.82

• 2276 reflections

• 149 parameters

• 1 restraint

• H atoms treated by a mixture of independent and constrained refinement

• Δρ_max = 0.15 e Å⁻³

• Δρ_min = −0.10 e Å⁻³

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, 1997 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶), DIAMOND (Brandenburg, 2002 ▶); software used to prepare material for publication: SHELXL97, PLATON (Spek, 2003 ▶) and WinGX (Farrugia, 1999 ▶).

Supplementary Material

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

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1i	0.826 (14)	2.117 (15)	2.9208 (14)	164.2 (15)

Symmetry code: (i) .

supplementary crystallographic information

Comment

In the present work, the structure of N-(4-methylphenyl)-benzamide (N4MPBA) has been determined to explore the effect of substituents on the structure of N-aromatic amides (Gowda et al., 2003, 2007a, b, c, d). The structure of N4MPBA (Fig. 1) resembles those of N-(2-chlorophenyl)-benzamide (N2CPBA) (Gowda et al., 2007a), 2-chloro-N-(phenyl)-benzamide (NP2CBA) (Gowda et al., 2003), N-(2,3-dichlorophenyl)benzamide (N23DCPBA) (Gowda et al., 2007b), N-(3,4-dichlorophenyl)-benzamide (N34DCPBA)(Gowda et al., 2007c) and 2-chloro-N- (2-chlorophenyl)benzamide (N2CP2CBA) (Gowda et al., 2007d), The bond parameters in N4MPBA are similar to those in N2CPBA, NP2CBA, N23DCPBA, N34DCPBA and N2CP2CBA. The molecules of N4MPBA are linked into chains in the direction of b axis through N—H···O hydrogen bonds (Table 1 and Fig. 2).

Experimental

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.

Refinement

H atoms bonded to C atoms were placed in geometrically calculated positions and subsequently treated as riding with C–H distances of 0.93Å for C_aromatic—H and C_methyl—H = 0.96 Å. The amino H atom was visible in difference map. In the refinement the N–H distance was restrained to 0.86 (5) Å. The U_iso(H) values were set at 1.2 U_eq(C,N) of the parent atom (1.5 for methyl).

Figures

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.

Partial packing diagram of the title compound showing the hydrogen bonds as dashed lines. Symmetry code (i): -x + 1/2, y - 1/2, z.

Crystal data

C14H13NO	F000 = 896
Mr = 211.25	Dx = 1.202 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 4170 reflections
a = 9.1117 (3) Å	θ = 3.1–29.4º
b = 9.8336 (2) Å	µ = 0.08 mm−1
c = 26.0616 (10) Å	T = 295 (2) K
V = 2335.14 (13) Å3	Prism, colourless
Z = 8	0.26 × 0.07 × 0.06 mm

Data collection

Oxford Diffraction Xcalibur diffractometer	1060 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.078
Detector resolution: 10.434 pixels mm-1	θmax = 26.0º
T = 295(2) K	θmin = 5.5º
ω scans with κ offsets	h = −11→11
Absorption correction: none	k = −10→12
21626 measured reflections	l = −32→32
2276 independent reflections

Refinement

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)] = 0.035	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.084	w = 1/[σ2(Fo2) + (0.0449P)2] where P = (Fo2 + 2Fc2)/3
S = 0.82	(Δ/σ)max = 0.002
2276 reflections	Δρmax = 0.15 e Å−3
149 parameters	Δρmin = −0.10 e Å−3
1 restraint	Extinction correction: none
Primary atom site location: structure-invariant direct methods

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
C1	0.17469 (16)	0.53524 (13)	0.35738 (6)	0.0451 (4)
C2	0.04977 (15)	0.47251 (12)	0.32925 (5)	0.0426 (4)
C3	−0.02778 (18)	0.55216 (14)	0.29516 (6)	0.0564 (4)
H3	−0.0029	0.6433	0.2912	0.068*
C4	−0.1411 (2)	0.49840 (16)	0.26710 (7)	0.0677 (5)
H4	−0.1916	0.5529	0.2439	0.081*
C5	−0.1804 (2)	0.36530 (16)	0.27305 (7)	0.0699 (5)
H5	−0.2574	0.3294	0.254	0.084*
C6	−0.10609 (19)	0.28486 (14)	0.30715 (7)	0.0637 (5)
H6	−0.1336	0.1945	0.3116	0.076*
C7	0.00930 (17)	0.33727 (13)	0.33495 (6)	0.0523 (4)
H7	0.0604	0.2818	0.3577	0.063*
C8	0.41205 (16)	0.49206 (13)	0.39957 (6)	0.0468 (4)
C9	0.4191 (2)	0.59367 (14)	0.43600 (6)	0.0568 (4)
H9	0.334	0.6383	0.4463	0.068*
C10	0.5522 (2)	0.62876 (16)	0.45704 (6)	0.0647 (5)
H10	0.5556	0.6985	0.4811	0.078*
C11	0.6797 (2)	0.56452 (16)	0.44375 (7)	0.0637 (5)
C12	0.6706 (2)	0.46213 (17)	0.40767 (7)	0.0746 (5)
H12	0.7554	0.4165	0.3978	0.089*
C13	0.53824 (19)	0.42617 (15)	0.38596 (7)	0.0664 (5)
H13	0.5348	0.3565	0.3619	0.08*
C14	0.8256 (2)	0.6010 (2)	0.46760 (8)	0.0961 (6)
H14A	0.8093	0.6467	0.4997	0.144*
H14B	0.8788	0.6599	0.4449	0.144*
H14C	0.8814	0.5197	0.4734	0.144*
N1	0.27740 (14)	0.45148 (11)	0.37649 (5)	0.0507 (4)
H1N	0.2724 (17)	0.3698 (15)	0.3692 (5)	0.061*
O1	0.18442 (12)	0.65930 (9)	0.36138 (5)	0.0701 (4)

Atomic displacement parameters (Ų)

	U11	U22	U33	U12	U13	U23
C1	0.0446 (9)	0.0321 (7)	0.0587 (10)	0.0027 (7)	0.0071 (8)	0.0021 (7)
C2	0.0402 (9)	0.0368 (7)	0.0507 (9)	0.0018 (7)	0.0047 (8)	−0.0009 (7)
C3	0.0597 (11)	0.0416 (8)	0.0680 (10)	0.0038 (8)	−0.0024 (10)	0.0023 (8)
C4	0.0723 (13)	0.0580 (10)	0.0728 (12)	0.0102 (9)	−0.0188 (10)	−0.0002 (8)
C5	0.0637 (12)	0.0671 (11)	0.0790 (13)	0.0011 (9)	−0.0185 (11)	−0.0146 (9)
C6	0.0634 (12)	0.0464 (9)	0.0812 (12)	−0.0078 (8)	−0.0085 (11)	−0.0025 (8)
C7	0.0505 (10)	0.0421 (8)	0.0643 (11)	−0.0002 (8)	−0.0041 (9)	0.0030 (7)
C8	0.0461 (10)	0.0365 (7)	0.0577 (10)	−0.0016 (8)	−0.0048 (8)	0.0016 (7)
C9	0.0591 (12)	0.0516 (8)	0.0596 (10)	0.0054 (8)	−0.0017 (9)	−0.0043 (8)
C10	0.0702 (14)	0.0606 (10)	0.0633 (11)	−0.0037 (10)	−0.0105 (11)	−0.0100 (8)
C11	0.0572 (12)	0.0660 (11)	0.0680 (12)	−0.0118 (9)	−0.0075 (10)	0.0018 (9)
C12	0.0497 (12)	0.0822 (11)	0.0918 (13)	0.0039 (10)	0.0009 (11)	−0.0187 (11)
C13	0.0523 (12)	0.0645 (10)	0.0824 (12)	0.0044 (9)	−0.0031 (10)	−0.0238 (8)
C14	0.0670 (14)	0.1123 (14)	0.1092 (16)	−0.0196 (11)	−0.0240 (13)	−0.0088 (12)
N1	0.0502 (9)	0.0308 (5)	0.0710 (9)	0.0014 (7)	−0.0082 (7)	−0.0033 (6)
O1	0.0606 (8)	0.0331 (6)	0.1165 (9)	0.0002 (5)	−0.0177 (7)	−0.0001 (5)

Geometric parameters (Å, °)

C1—O1	1.2276 (13)	C8—C9	1.380 (2)
C1—N1	1.3425 (17)	C8—N1	1.4235 (18)
C1—C2	1.4878 (19)	C9—C10	1.375 (2)
C2—C3	1.3792 (19)	C9—H9	0.93
C2—C7	1.3880 (18)	C10—C11	1.367 (2)
C3—C4	1.371 (2)	C10—H10	0.93
C3—H3	0.93	C11—C12	1.380 (2)
C4—C5	1.366 (2)	C11—C14	1.511 (2)
C4—H4	0.93	C12—C13	1.378 (2)
C5—C6	1.369 (2)	C12—H12	0.93
C5—H5	0.93	C13—H13	0.93
C6—C7	1.377 (2)	C14—H14A	0.96
C6—H6	0.93	C14—H14B	0.96
C7—H7	0.93	C14—H14C	0.96
C8—C13	1.367 (2)	N1—H1N	0.826 (14)
O1—C1—N1	121.86 (14)	C10—C9—C8	119.79 (16)
O1—C1—C2	120.61 (13)	C10—C9—H9	120.1
N1—C1—C2	117.50 (11)	C8—C9—H9	120.1
C3—C2—C7	118.48 (13)	C11—C10—C9	122.19 (15)
C3—C2—C1	118.29 (11)	C11—C10—H10	118.9
C7—C2—C1	123.22 (13)	C9—C10—H10	118.9
C4—C3—C2	120.69 (13)	C10—C11—C12	117.29 (16)
C4—C3—H3	119.7	C10—C11—C14	122.26 (17)
C2—C3—H3	119.7	C12—C11—C14	120.44 (17)
C5—C4—C3	120.40 (15)	C13—C12—C11	121.31 (16)
C5—C4—H4	119.8	C13—C12—H12	119.3
C3—C4—H4	119.8	C11—C12—H12	119.3
C4—C5—C6	119.87 (15)	C8—C13—C12	120.52 (15)
C4—C5—H5	120.1	C8—C13—H13	119.7
C6—C5—H5	120.1	C12—C13—H13	119.7
C5—C6—C7	120.19 (14)	C11—C14—H14A	109.5
C5—C6—H6	119.9	C11—C14—H14B	109.5
C7—C6—H6	119.9	H14A—C14—H14B	109.5
C6—C7—C2	120.34 (14)	C11—C14—H14C	109.5
C6—C7—H7	119.8	H14A—C14—H14C	109.5
C2—C7—H7	119.8	H14B—C14—H14C	109.5
C13—C8—C9	118.87 (15)	C1—N1—C8	125.84 (11)
C13—C8—N1	118.86 (13)	C1—N1—H1N	118.2 (11)
C9—C8—N1	122.26 (14)	C8—N1—H1N	114.6 (11)
O1—C1—C2—C3	19.6 (2)	N1—C8—C9—C10	180.00 (13)
N1—C1—C2—C3	−158.31 (13)	C8—C9—C10—C11	−1.1 (2)
O1—C1—C2—C7	−161.61 (14)	C9—C10—C11—C12	0.4 (2)
N1—C1—C2—C7	20.5 (2)	C9—C10—C11—C14	−178.73 (15)
C7—C2—C3—C4	−0.8 (2)	C10—C11—C12—C13	0.0 (3)
C1—C2—C3—C4	178.06 (14)	C14—C11—C12—C13	179.16 (17)
C2—C3—C4—C5	0.9 (2)	C9—C8—C13—C12	−1.0 (2)
C3—C4—C5—C6	−0.1 (3)	N1—C8—C13—C12	−179.66 (14)
C4—C5—C6—C7	−0.9 (3)	C11—C12—C13—C8	0.3 (3)
C5—C6—C7—C2	1.0 (2)	O1—C1—N1—C8	−5.0 (2)
C3—C2—C7—C6	−0.2 (2)	C2—C1—N1—C8	172.86 (13)
C1—C2—C7—C6	−178.97 (14)	C13—C8—N1—C1	−134.60 (15)
C13—C8—C9—C10	1.4 (2)	C9—C8—N1—C1	46.8 (2)

Hydrogen-bond geometry (Å, °)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1i	0.826 (14)	2.117 (15)	2.9208 (14)	164.2 (15)

Symmetry codes: (i) −x+1/2, y−1/2, z.