2-Methyl-N-phenyl-benzamide.

In the structure of the title compound (NP2MBA), C(14)H(13)NO, 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-phenyl-benzamide, with similar bond parameters. The dihedral angle between the phenyl and benzoyl rings is 88.05 (5)°. Mol-ecules 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 = 211.25

Orthorhombic,

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 ▶) 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[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.115

S = 1.05

2387 reflections

149 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.24 e Å−3

Δρmin = −0.21 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2004 ▶); 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: SHELXS97.

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

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

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

C14H13NO	F000 = 896
Mr = 211.25	Dx = 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 = 1.5–26.9º
b = 8.6824 (6) Å	µ = 0.08 mm−1
c = 18.710 (1) Å	T = 100 (2) K
V = 2339.9 (3) Å3	Rod, colourless
Z = 8	0.40 × 0.20 × 0.16 mm

Oxford Diffraction Xcalibur diffractometer with Sapphire CCD Detector	2387 independent reflections
Radiation source: fine-focus sealed tube	1686 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.029
T = 100(2) K	θmax = 26.4º
Rotation method data acquisition using ω and φ scans.	θmin = 2.6º
Absorption correction: multi-scan(SCALE3 ABSPACK; Oxford Diffraction, 2007)	h = −17→17
Tmin = 0.970, Tmax = 0.981	k = −10→10
11005 measured reflections	l = −23→23

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)] = 0.038	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.115	w = 1/[σ2(Fo2) + (0.0589P)2 + 0.6762P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max = 0.007
2387 reflections	Δρmax = 0.24 e Å−3
149 parameters	Δρmin = −0.21 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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
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)

	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)

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)

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)

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) .