3-Methyl-N-phen-ylbenzamide.

The conformation of the C=O bond in the structure of the title compound, C(14)H(13)NO, is anti to the meta-methyl substituent in the benzoyl ring. The conformations of the N-H and C=O bonds in the amide group are also anti to each other. The asymmetric unit of the structure contains two mol-ecules. The bond parameters are similar to those in N-(phen-yl)benzamide, 2-methyl-N-(phenyl)-benz-amide and other benzanilides. The amide group -NHCO- forms dihedral angles of 20.97 (34) and 45.65 (19)° with the benzoyl rings, and 41.54 (25) and 31.87 (29)° with the aniline rings, in the two independent mol-ecules. The benzoyl and aniline rings adopt dihedral angles of 22.17 (18) and 75.86 (12)° in the two independent mol-ecules. In the crystal structure, mol-ecules are linked into chains by inter-molecular N-H⋯O hydrogen bonds.

Related literature

For related literature, see: Gowda et al. (2003 ▶, 2008a ▶,b ▶).

Experimental

Crystal data

C14H13NO

M = 211.25

Monoclinic,

a = 16.947 (2) Å

b = 15.531 (1) Å

c = 8.623 (1) Å

β = 93.35 (1)°

V = 2265.7 (4) Å3

Z = 8

Cu Kα radiation

μ = 0.62 mm−1

T = 299 (2) K

0.60 × 0.10 × 0.05 mm

Data collection

Enraf–Nonius CAD4 diffractometer

Absorption correction: none

4339 measured reflections

4039 independent reflections

2466 reflections with I > 2σ(I)

R int = 0.034

3 standard reflections frequency: 120 min intensity decay: 1.5%

Refinement

R[F 2 > 2σ(F 2)] = 0.082

wR(F 2) = 0.240

S = 1.03

4039 reflections

291 parameters

H-atom parameters constrained

Δρmax = 0.35 e Å−3

Δρmin = −0.39 e Å−3

Data collection: CAD-4-PC Software (Enraf–Nonius, 1996 ▶); cell refinement: CAD-4-PC Software; data reduction: REDU4 (Stoe & Cie, 1987 ▶); 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: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808008143/dn2328sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808008143/dn2328Isup2.hkl

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

C14H13NO	F000 = 896
Mr = 211.25	Dx = 1.239 Mg m−3
Monoclinic, P21/c	Cu Kα radiation λ = 1.54180 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 16.947 (2) Å	θ = 5.7–21.0º
b = 15.531 (1) Å	µ = 0.62 mm−1
c = 8.623 (1) Å	T = 299 (2) K
β = 93.35 (1)º	Long needle, colourless
V = 2265.7 (4) Å3	0.60 × 0.10 × 0.05 mm
Z = 8

Enraf–Nonius CAD4 diffractometer	Rint = 0.034
Radiation source: fine-focus sealed tube	θmax = 66.9º
Monochromator: graphite	θmin = 2.6º
T = 299(2) K	h = −20→20
ω/2θ scans	k = −1→18
Absorption correction: none	l = −10→0
4339 measured reflections	3 standard reflections
4039 independent reflections	every 120 min
2466 reflections with I > 2σ(I)	intensity decay: 1.5%

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)] = 0.082	H-atom parameters constrained
wR(F2) = 0.241	w = 1/[σ2(Fo2) + (0.153P)2] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max = 0.003
4039 reflections	Δρmax = 0.36 e Å−3
291 parameters	Δρmin = −0.39 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
O1	0.24023 (18)	0.66029 (17)	0.5392 (3)	0.0558 (8)
N1	0.26569 (16)	0.75059 (19)	0.3424 (3)	0.0399 (7)
H1N	0.2562	0.7611	0.2452	0.048*
C1	0.3146 (2)	0.8100 (2)	0.4286 (3)	0.0363 (7)
C2	0.3052 (2)	0.8972 (2)	0.3996 (4)	0.0457 (9)
H2	0.2686	0.9159	0.3224	0.055*
C3	0.3502 (3)	0.9564 (3)	0.4849 (5)	0.0559 (10)
H3	0.3435	1.0150	0.4660	0.067*
C4	0.4049 (3)	0.9287 (3)	0.5978 (5)	0.0662 (12)
H4	0.4342	0.9687	0.6571	0.079*
C5	0.4163 (3)	0.8422 (3)	0.6235 (5)	0.0611 (12)
H5	0.4545	0.8237	0.6980	0.073*
C6	0.3711 (2)	0.7827 (3)	0.5385 (4)	0.0481 (9)
H6	0.3789	0.7241	0.5557	0.058*
C7	0.2328 (2)	0.6791 (2)	0.3997 (4)	0.0378 (8)
C8	0.1875 (2)	0.6216 (2)	0.2875 (4)	0.0382 (8)
C9	0.1563 (2)	0.6497 (2)	0.1438 (4)	0.0395 (8)
H9	0.1620	0.7071	0.1158	0.047*
C10	0.1167 (2)	0.5932 (3)	0.0411 (4)	0.0469 (9)
C11	0.1086 (2)	0.5083 (3)	0.0854 (5)	0.0553 (10)
H11	0.0830	0.4695	0.0173	0.066*
C12	0.1378 (3)	0.4802 (3)	0.2293 (5)	0.0598 (11)
H12	0.1308	0.4232	0.2587	0.072*
C13	0.1775 (2)	0.5369 (2)	0.3297 (5)	0.0505 (9)
H13	0.1976	0.5177	0.4263	0.061*
C14	0.0866 (3)	0.6228 (3)	−0.1174 (4)	0.0639 (12)
H14A	0.0874	0.6846	−0.1213	0.077*
H14B	0.0334	0.6027	−0.1380	0.077*
H14C	0.1197	0.6001	−0.1942	0.077*
O2	0.26730 (16)	0.32575 (17)	−0.0183 (3)	0.0498 (7)
N2	0.22500 (17)	0.24790 (19)	0.1854 (3)	0.0416 (7)
H2N	0.2375	0.2335	0.2799	0.050*
C15	0.1546 (2)	0.2116 (2)	0.1191 (4)	0.0396 (8)
C16	0.1310 (3)	0.1321 (2)	0.1709 (4)	0.0538 (10)
H16	0.1638	0.1014	0.2413	0.065*
C17	0.0593 (3)	0.0978 (3)	0.1193 (5)	0.0673 (13)
H17	0.0429	0.0453	0.1581	0.081*
C18	0.0117 (3)	0.1414 (3)	0.0100 (5)	0.0664 (12)
H18	−0.0365	0.1181	−0.0258	0.080*
C19	0.0360 (3)	0.2189 (3)	−0.0454 (5)	0.0603 (11)
H19	0.0046	0.2477	−0.1207	0.072*
C20	0.1070 (2)	0.2549 (3)	0.0098 (4)	0.0453 (9)
H20	0.1226	0.3083	−0.0268	0.054*
C21	0.2752 (2)	0.3022 (2)	0.1197 (4)	0.0386 (8)
C22	0.3426 (2)	0.3328 (2)	0.2230 (4)	0.0384 (8)
C23	0.3317 (2)	0.3609 (2)	0.3741 (4)	0.0427 (8)
H23	0.2813	0.3599	0.4114	0.051*
C24	0.3942 (2)	0.3902 (2)	0.4689 (4)	0.0458 (9)
C25	0.4691 (2)	0.3895 (2)	0.4135 (5)	0.0503 (9)
H25	0.5121	0.4079	0.4772	0.060*
C26	0.4808 (2)	0.3617 (3)	0.2633 (5)	0.0529 (10)
H26	0.5314	0.3614	0.2270	0.063*
C27	0.4178 (2)	0.3347 (2)	0.1686 (4)	0.0462 (9)
H27	0.4257	0.3176	0.0673	0.055*
C28	0.3808 (3)	0.4223 (3)	0.6316 (5)	0.0706 (14)
H28A	0.3665	0.3748	0.6955	0.085*
H28B	0.3391	0.4642	0.6270	0.085*
H28C	0.4285	0.4483	0.6753	0.085*

	U11	U22	U33	U12	U13	U23
O1	0.095 (2)	0.0574 (16)	0.0143 (12)	−0.0142 (14)	−0.0011 (12)	0.0030 (10)
N1	0.0552 (17)	0.0488 (16)	0.0154 (12)	−0.0071 (14)	−0.0001 (12)	−0.0003 (11)
C1	0.0451 (18)	0.0481 (19)	0.0160 (14)	−0.0036 (15)	0.0039 (13)	−0.0036 (13)
C2	0.056 (2)	0.054 (2)	0.0275 (18)	−0.0009 (17)	0.0043 (16)	0.0017 (15)
C3	0.076 (3)	0.047 (2)	0.044 (2)	−0.0084 (19)	0.001 (2)	−0.0009 (17)
C4	0.087 (3)	0.065 (3)	0.045 (2)	−0.020 (2)	−0.006 (2)	−0.011 (2)
C5	0.068 (3)	0.073 (3)	0.040 (2)	−0.011 (2)	−0.016 (2)	0.002 (2)
C6	0.056 (2)	0.051 (2)	0.037 (2)	−0.0034 (17)	−0.0014 (17)	0.0017 (16)
C7	0.0488 (19)	0.0458 (19)	0.0191 (15)	0.0027 (15)	0.0043 (14)	−0.0037 (14)
C8	0.048 (2)	0.0444 (19)	0.0229 (16)	−0.0005 (15)	0.0054 (14)	−0.0051 (13)
C9	0.0483 (19)	0.0498 (19)	0.0204 (16)	−0.0092 (16)	0.0036 (14)	−0.0035 (14)
C10	0.050 (2)	0.061 (2)	0.0303 (19)	−0.0054 (17)	0.0034 (16)	−0.0093 (16)
C11	0.059 (2)	0.059 (2)	0.047 (2)	−0.011 (2)	0.0019 (19)	−0.0190 (19)
C12	0.079 (3)	0.042 (2)	0.058 (3)	−0.008 (2)	−0.005 (2)	−0.0042 (18)
C13	0.069 (3)	0.045 (2)	0.037 (2)	−0.0001 (18)	−0.0004 (18)	0.0015 (16)
C14	0.069 (3)	0.090 (3)	0.031 (2)	−0.014 (2)	−0.0042 (19)	−0.008 (2)
O2	0.0733 (18)	0.0608 (16)	0.0150 (11)	−0.0113 (13)	0.0008 (11)	0.0021 (10)
N2	0.0548 (17)	0.0534 (17)	0.0163 (13)	−0.0067 (14)	−0.0002 (12)	0.0036 (12)
C15	0.050 (2)	0.050 (2)	0.0192 (15)	−0.0040 (16)	0.0036 (14)	−0.0074 (14)
C16	0.079 (3)	0.052 (2)	0.0304 (19)	−0.008 (2)	0.0043 (18)	−0.0029 (16)
C17	0.088 (3)	0.070 (3)	0.044 (2)	−0.029 (3)	0.006 (2)	−0.008 (2)
C18	0.066 (3)	0.089 (3)	0.044 (2)	−0.021 (2)	0.003 (2)	−0.014 (2)
C19	0.062 (2)	0.081 (3)	0.037 (2)	0.004 (2)	−0.0015 (19)	−0.008 (2)
C20	0.052 (2)	0.058 (2)	0.0252 (17)	0.0003 (18)	0.0017 (15)	−0.0019 (15)
C21	0.0509 (19)	0.0455 (19)	0.0197 (15)	0.0023 (15)	0.0041 (14)	−0.0045 (13)
C22	0.050 (2)	0.0424 (19)	0.0223 (16)	−0.0011 (15)	0.0013 (14)	0.0011 (13)
C23	0.052 (2)	0.051 (2)	0.0248 (17)	−0.0048 (16)	0.0032 (15)	−0.0019 (15)
C24	0.060 (2)	0.048 (2)	0.0282 (18)	−0.0052 (17)	−0.0064 (17)	−0.0034 (15)
C25	0.054 (2)	0.053 (2)	0.043 (2)	−0.0016 (17)	−0.0085 (18)	0.0002 (17)
C26	0.047 (2)	0.060 (2)	0.052 (2)	0.0024 (18)	0.0040 (18)	0.0027 (19)
C27	0.054 (2)	0.053 (2)	0.0325 (19)	0.0030 (17)	0.0077 (16)	−0.0011 (16)
C28	0.085 (3)	0.092 (3)	0.034 (2)	−0.021 (3)	−0.002 (2)	−0.023 (2)

O1—C7	1.237 (4)	O2—C21	1.244 (4)
N1—C7	1.348 (4)	N2—C21	1.347 (4)
N1—C1	1.421 (4)	N2—C15	1.409 (4)
N1—H1N	0.8600	N2—H2N	0.8600
C1—C6	1.373 (5)	C15—C20	1.379 (5)
C1—C2	1.385 (5)	C15—C16	1.382 (5)
C2—C3	1.379 (5)	C16—C17	1.376 (6)
C2—H2	0.9300	C16—H16	0.9300
C3—C4	1.373 (6)	C17—C18	1.381 (7)
C3—H3	0.9300	C17—H17	0.9300
C4—C5	1.373 (6)	C18—C19	1.368 (6)
C4—H4	0.9300	C18—H18	0.9300
C5—C6	1.384 (5)	C19—C20	1.386 (5)
C5—H5	0.9300	C19—H19	0.9300
C6—H6	0.9300	C20—H20	0.9300
C7—C8	1.496 (5)	C21—C22	1.484 (5)
C8—C13	1.378 (5)	C22—C27	1.384 (5)
C8—C9	1.389 (5)	C22—C23	1.397 (5)
C9—C10	1.391 (5)	C23—C24	1.376 (5)
C9—H9	0.9300	C23—H23	0.9300
C10—C11	1.382 (6)	C24—C25	1.383 (6)
C10—C14	1.503 (5)	C24—C28	1.519 (5)
C11—C12	1.380 (6)	C25—C26	1.391 (6)
C11—H11	0.9300	C25—H25	0.9300
C12—C13	1.382 (5)	C26—C27	1.372 (5)
C12—H12	0.9300	C26—H26	0.9300
C13—H13	0.9300	C27—H27	0.9300
C14—H14A	0.9600	C28—H28A	0.9600
C14—H14B	0.9600	C28—H28B	0.9600
C14—H14C	0.9600	C28—H28C	0.9600
C7—N1—C1	125.7 (3)	C21—N2—C15	128.3 (3)
C7—N1—H1N	117.1	C21—N2—H2N	115.8
C1—N1—H1N	117.1	C15—N2—H2N	115.8
C6—C1—C2	119.6 (3)	C20—C15—C16	119.2 (3)
C6—C1—N1	121.5 (3)	C20—C15—N2	122.0 (3)
C2—C1—N1	118.9 (3)	C16—C15—N2	118.8 (3)
C3—C2—C1	120.2 (4)	C17—C16—C15	120.6 (4)
C3—C2—H2	119.9	C17—C16—H16	119.7
C1—C2—H2	119.9	C15—C16—H16	119.7
C4—C3—C2	119.8 (4)	C16—C17—C18	120.0 (4)
C4—C3—H3	120.1	C16—C17—H17	120.0
C2—C3—H3	120.1	C18—C17—H17	120.0
C5—C4—C3	120.3 (4)	C19—C18—C17	119.6 (4)
C5—C4—H4	119.8	C19—C18—H18	120.2
C3—C4—H4	119.8	C17—C18—H18	120.2
C4—C5—C6	119.9 (4)	C18—C19—C20	120.6 (4)
C4—C5—H5	120.0	C18—C19—H19	119.7
C6—C5—H5	120.0	C20—C19—H19	119.7
C1—C6—C5	120.1 (4)	C15—C20—C19	119.9 (4)
C1—C6—H6	120.0	C15—C20—H20	120.0
C5—C6—H6	120.0	C19—C20—H20	120.0
O1—C7—N1	122.0 (3)	O2—C21—N2	123.4 (3)
O1—C7—C8	120.4 (3)	O2—C21—C22	121.1 (3)
N1—C7—C8	117.5 (3)	N2—C21—C22	115.5 (3)
C13—C8—C9	119.3 (3)	C27—C22—C23	118.9 (3)
C13—C8—C7	117.8 (3)	C27—C22—C21	119.7 (3)
C9—C8—C7	123.0 (3)	C23—C22—C21	121.4 (3)
C8—C9—C10	121.0 (3)	C24—C23—C22	121.2 (3)
C8—C9—H9	119.5	C24—C23—H23	119.4
C10—C9—H9	119.5	C22—C23—H23	119.4
C11—C10—C9	118.5 (4)	C23—C24—C25	118.9 (3)
C11—C10—C14	120.7 (4)	C23—C24—C28	120.4 (4)
C9—C10—C14	120.8 (4)	C25—C24—C28	120.7 (4)
C12—C11—C10	121.0 (4)	C24—C25—C26	120.5 (4)
C12—C11—H11	119.5	C24—C25—H25	119.7
C10—C11—H11	119.5	C26—C25—H25	119.7
C11—C12—C13	119.9 (4)	C27—C26—C25	120.1 (4)
C11—C12—H12	120.1	C27—C26—H26	120.0
C13—C12—H12	120.1	C25—C26—H26	120.0
C8—C13—C12	120.4 (4)	C26—C27—C22	120.4 (4)
C8—C13—H13	119.8	C26—C27—H27	119.8
C12—C13—H13	119.8	C22—C27—H27	119.8
C10—C14—H14A	109.5	C24—C28—H28A	109.5
C10—C14—H14B	109.5	C24—C28—H28B	109.5
H14A—C14—H14B	109.5	H28A—C28—H28B	109.5
C10—C14—H14C	109.5	C24—C28—H28C	109.5
H14A—C14—H14C	109.5	H28A—C28—H28C	109.5
H14B—C14—H14C	109.5	H28B—C28—H28C	109.5
C7—N1—C1—C6	40.6 (5)	C21—N2—C15—C20	−32.3 (5)
C7—N1—C1—C2	−139.9 (4)	C21—N2—C15—C16	150.9 (4)
C6—C1—C2—C3	−2.6 (5)	C20—C15—C16—C17	−2.7 (6)
N1—C1—C2—C3	178.0 (3)	N2—C15—C16—C17	174.2 (4)
C1—C2—C3—C4	0.6 (6)	C15—C16—C17—C18	2.7 (7)
C2—C3—C4—C5	1.6 (7)	C16—C17—C18—C19	−0.6 (7)
C3—C4—C5—C6	−1.9 (7)	C17—C18—C19—C20	−1.5 (7)
C2—C1—C6—C5	2.3 (5)	C16—C15—C20—C19	0.7 (5)
N1—C1—C6—C5	−178.2 (4)	N2—C15—C20—C19	−176.2 (3)
C4—C5—C6—C1	−0.1 (6)	C18—C19—C20—C15	1.4 (6)
C1—N1—C7—O1	3.1 (6)	C15—N2—C21—O2	−3.5 (6)
C1—N1—C7—C8	−176.0 (3)	C15—N2—C21—C22	177.0 (3)
O1—C7—C8—C13	−21.2 (5)	O2—C21—C22—C27	−44.0 (5)
N1—C7—C8—C13	157.9 (3)	N2—C21—C22—C27	135.6 (3)
O1—C7—C8—C9	159.5 (3)	O2—C21—C22—C23	135.1 (4)
N1—C7—C8—C9	−21.4 (5)	N2—C21—C22—C23	−45.3 (5)
C13—C8—C9—C10	−1.4 (5)	C27—C22—C23—C24	−0.1 (5)
C7—C8—C9—C10	177.9 (3)	C21—C22—C23—C24	−179.2 (3)
C8—C9—C10—C11	0.4 (6)	C22—C23—C24—C25	−1.5 (6)
C8—C9—C10—C14	−176.9 (4)	C22—C23—C24—C28	178.6 (4)
C9—C10—C11—C12	1.1 (6)	C23—C24—C25—C26	1.5 (6)
C14—C10—C11—C12	178.4 (4)	C28—C24—C25—C26	−178.7 (4)
C10—C11—C12—C13	−1.6 (7)	C24—C25—C26—C27	0.1 (6)
C9—C8—C13—C12	0.9 (6)	C25—C26—C27—C22	−1.7 (6)
C7—C8—C13—C12	−178.5 (4)	C23—C22—C27—C26	1.7 (5)
C11—C12—C13—C8	0.6 (7)	C21—C22—C27—C26	−179.2 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1i	0.86	2.16	2.968 (4)	157
N2—H2N···O2ii	0.86	2.01	2.853 (3)	168

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1i	0.86	2.16	2.968 (4)	157
N2—H2N⋯O2ii	0.86	2.01	2.853 (3)	168

Symmetry codes: (i) ; (ii) .