N-(3,5-Dimethyl-phen-yl)-2-methyl-benzamide.

In the mol-ecular structure of the title compound, C(16)H(17)NO, the amide group is twisted by 41.8 (2) and 29.0 (2)° out of the planes of the 2-methyl-phenyl and 3,5-dimethyl-phenyl rings, respectively. The two aromatic rings make a dihedral angle of 69.5 (1)°. In the crystal, inter-molecular N-H⋯O hydrogen bonds connect the mol-ecules into C(4) chains running along the c axis.

Related literature

For our study of the effect of the substituents on the structures of benzanilides and for related structures, see: Gowda, Foro et al. (2008 ▶); Gowda, Tokarčík et al. (2009 ▶). For synthesis, see: Gowda, Foro et al. (2008b ▶).

Experimental

Crystal data

C16H17NO

M = 239.31

Monoclinic,

a = 10.5174 (5) Å

b = 14.9616 (7) Å

c = 8.9209 (4) Å

β = 105.373 (4)°

V = 1353.54 (11) Å3

Z = 4

Mo Kα radiation

μ = 0.07 mm−1

T = 295 K

0.54 × 0.08 × 0.04 mm

Data collection

Oxford Diffraction Xcalibur Ruby Gemini diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009 ▶) T min = 0.957, T max = 0.992

14671 measured reflections

2548 independent reflections

1628 reflections with I > 2σ(I)

R int = 0.041

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.120

S = 0.97

2548 reflections

170 parameters

H-atom parameters constrained

Δρmax = 0.13 e Å−3

Δρmin = −0.12 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 ▶); 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 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810009116/tk2640sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810009116/tk2640Isup2.hkl

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

C16H17NO	F(000) = 512
Mr = 239.31	Dx = 1.174 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5268 reflections
a = 10.5174 (5) Å	θ = 2.0–29.4°
b = 14.9616 (7) Å	µ = 0.07 mm−1
c = 8.9209 (4) Å	T = 295 K
β = 105.373 (4)°	Needle, colourless
V = 1353.54 (11) Å3	0.54 × 0.08 × 0.04 mm
Z = 4

Oxford Diffraction Xcalibur Ruby Gemini diffractometer	2548 independent reflections
graphite	1628 reflections with I > 2σ(I)
Detector resolution: 10.434 pixels mm-1	Rint = 0.041
ω scans	θmax = 25.6°, θmin = 2.0°
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	h = −12→12
Tmin = 0.957, Tmax = 0.992	k = −18→18
14671 measured reflections	l = −10→10

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.120	H-atom parameters constrained
S = 0.97	[exp(2.50(sinθ/λ)2)]/[σ2(Fo2) + (0.094P)2], where P = 0.33333Fo2 + 0.66667Fc2
2548 reflections	(Δ/σ)max < 0.001
170 parameters	Δρmax = 0.13 e Å−3
0 restraints	Δρmin = −0.12 e Å−3

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.

	x	y	z	Uiso*/Ueq	Occ. (<1)
C1	0.20367 (15)	0.19330 (10)	0.08175 (15)	0.0348 (4)
C2	0.09976 (16)	0.14838 (10)	0.14205 (17)	0.0392 (4)
C3	−0.02376 (17)	0.12792 (12)	0.0426 (2)	0.0503 (5)
C4	−0.1141 (2)	0.08515 (16)	0.1073 (3)	0.0724 (6)
H4	−0.1967	0.0705	0.0435	0.087*
C5	−0.0850 (2)	0.06389 (17)	0.2623 (3)	0.0835 (7)
H5	−0.148	0.0359	0.3021	0.1*
C6	0.0366 (2)	0.08381 (16)	0.3589 (3)	0.0760 (7)
H6	0.0564	0.0695	0.464	0.091*
C7	0.1290 (2)	0.12525 (12)	0.29829 (19)	0.0527 (5)
H7	0.2121	0.1379	0.3629	0.063*
C8	0.38098 (14)	0.30756 (10)	0.15513 (15)	0.0354 (4)
C9	0.46745 (15)	0.27564 (11)	0.07407 (16)	0.0396 (4)
H9	0.4536	0.2198	0.0266	0.048*
C10	0.57512 (15)	0.32734 (12)	0.06388 (17)	0.0454 (4)
C11	0.59283 (16)	0.41058 (12)	0.13406 (18)	0.0489 (4)
H11	0.6637	0.4456	0.1256	0.059*
C12	0.50798 (17)	0.44351 (11)	0.21670 (17)	0.0449 (4)
C13	0.40205 (16)	0.39107 (11)	0.22612 (16)	0.0398 (4)
H13	0.344	0.4119	0.2807	0.048*
C14	−0.0633 (2)	0.15265 (17)	−0.1269 (2)	0.0743 (6)
H14A	−0.1568	0.1457	−0.1673	0.112*	0.82 (3)
H14B	−0.0187	0.1144	−0.1829	0.112*	0.82 (3)
H14C	−0.0395	0.2137	−0.1386	0.112*	0.82 (3)
H14D	0.0135	0.1703	−0.1585	0.112*	0.18 (3)
H14E	−0.1248	0.2014	−0.143	0.112*	0.18 (3)
H14F	−0.1037	0.1021	−0.1872	0.112*	0.18 (3)
C15	0.67092 (19)	0.29122 (17)	−0.0193 (2)	0.0651 (6)
H15A	0.7143	0.34	−0.0554	0.098*	0.60 (3)
H15B	0.6244	0.2558	−0.1063	0.098*	0.60 (3)
H15C	0.7353	0.2548	0.0507	0.098*	0.60 (3)
H15D	0.6684	0.2271	−0.0186	0.098*	0.40 (3)
H15E	0.7583	0.3112	0.0324	0.098*	0.40 (3)
H15F	0.6474	0.3123	−0.1247	0.098*	0.40 (3)
C16	0.5318 (2)	0.53329 (13)	0.2949 (2)	0.0644 (5)
H16A	0.5572	0.5754	0.227	0.097*	0.73 (2)
H16B	0.6009	0.5283	0.3896	0.097*	0.73 (2)
H16C	0.4525	0.5535	0.3182	0.097*	0.73 (2)
H16D	0.5166	0.5294	0.3962	0.097*	0.27 (2)
H16E	0.4728	0.5765	0.2336	0.097*	0.27 (2)
H16F	0.6213	0.5513	0.305	0.097*	0.27 (2)
N1	0.27245 (13)	0.25733 (9)	0.17550 (13)	0.0399 (3)
H1N	0.2474	0.2691	0.2576	0.048*
O1	0.22394 (11)	0.17203 (8)	−0.04280 (11)	0.0456 (3)

	U11	U22	U33	U12	U13	U23
C1	0.0372 (8)	0.0346 (8)	0.0317 (7)	0.0014 (7)	0.0078 (6)	0.0008 (6)
C2	0.0428 (9)	0.0315 (8)	0.0444 (8)	−0.0029 (7)	0.0137 (7)	−0.0046 (6)
C3	0.0426 (10)	0.0445 (10)	0.0629 (11)	−0.0037 (8)	0.0122 (8)	−0.0086 (8)
C4	0.0485 (11)	0.0649 (14)	0.1019 (16)	−0.0159 (10)	0.0167 (11)	−0.0023 (12)
C5	0.0744 (16)	0.0734 (16)	0.1135 (19)	−0.0260 (13)	0.0438 (15)	0.0144 (13)
C6	0.0901 (17)	0.0724 (15)	0.0719 (12)	−0.0242 (13)	0.0327 (12)	0.0169 (11)
C7	0.0602 (11)	0.0481 (10)	0.0506 (10)	−0.0128 (8)	0.0163 (8)	0.0044 (8)
C8	0.0360 (8)	0.0395 (9)	0.0290 (7)	−0.0040 (7)	0.0056 (6)	0.0048 (6)
C9	0.0396 (9)	0.0428 (9)	0.0341 (7)	−0.0008 (7)	0.0055 (6)	0.0004 (6)
C10	0.0359 (9)	0.0604 (11)	0.0377 (8)	−0.0007 (8)	0.0058 (6)	0.0074 (7)
C11	0.0387 (9)	0.0580 (11)	0.0463 (8)	−0.0133 (8)	0.0050 (7)	0.0113 (8)
C12	0.0486 (10)	0.0413 (9)	0.0399 (8)	−0.0071 (8)	0.0031 (7)	0.0065 (7)
C13	0.0444 (9)	0.0393 (9)	0.0354 (7)	−0.0013 (7)	0.0101 (6)	0.0020 (6)
C14	0.0483 (11)	0.1004 (18)	0.0638 (12)	−0.0075 (12)	−0.0037 (9)	−0.0105 (11)
C15	0.0441 (10)	0.0897 (16)	0.0651 (11)	0.0000 (10)	0.0209 (9)	−0.0018 (10)
C16	0.0745 (14)	0.0471 (11)	0.0683 (11)	−0.0196 (10)	0.0134 (10)	−0.0037 (9)
N1	0.0461 (8)	0.0433 (8)	0.0341 (6)	−0.0087 (6)	0.0173 (5)	−0.0051 (5)
O1	0.0505 (7)	0.0517 (7)	0.0363 (6)	−0.0048 (6)	0.0148 (5)	−0.0068 (5)

C1—O1	1.2276 (17)	C12—C13	1.383 (2)
C1—N1	1.3490 (19)	C12—C16	1.504 (2)
C1—C2	1.499 (2)	C13—H13	0.93
C2—C7	1.389 (2)	C14—H14A	0.96
C2—C3	1.399 (2)	C14—H14B	0.96
C3—C4	1.391 (3)	C14—H14C	0.96
C3—C14	1.504 (3)	C14—H14D	0.96
C4—C5	1.372 (3)	C14—H14E	0.96
C4—H4	0.93	C14—H14F	0.96
C5—C6	1.372 (3)	C15—H15A	0.96
C5—H5	0.93	C15—H15B	0.96
C6—C7	1.378 (3)	C15—H15C	0.96
C6—H6	0.93	C15—H15D	0.96
C7—H7	0.93	C15—H15E	0.96
C8—C9	1.388 (2)	C15—H15F	0.96
C8—C13	1.392 (2)	C16—H16A	0.96
C8—N1	1.4180 (19)	C16—H16B	0.96
C9—C10	1.394 (2)	C16—H16C	0.96
C9—H9	0.93	C16—H16D	0.96
C10—C11	1.384 (2)	C16—H16E	0.96
C10—C15	1.501 (3)	C16—H16F	0.96
C11—C12	1.390 (2)	N1—H1N	0.86
C11—H11	0.93
O1—C1—N1	123.50 (13)	C11—C12—C16	120.75 (16)
O1—C1—C2	121.78 (13)	C12—C13—C8	121.01 (15)
N1—C1—C2	114.72 (12)	C12—C13—H13	119.5
C7—C2—C3	120.21 (16)	C8—C13—H13	119.5
C7—C2—C1	118.90 (15)	C3—C14—H14A	109.5
C3—C2—C1	120.87 (14)	C3—C14—H14B	109.5
C4—C3—C2	117.28 (17)	C3—C14—H14C	109.5
C4—C3—C14	119.57 (18)	C3—C14—H14D	109.5
C2—C3—C14	123.12 (16)	C3—C14—H14E	109.5
C5—C4—C3	122.1 (2)	H14D—C14—H14E	109.5
C5—C4—H4	119	C3—C14—H14F	109.5
C3—C4—H4	119	H14D—C14—H14F	109.5
C4—C5—C6	120.27 (19)	H14E—C14—H14F	109.5
C4—C5—H5	119.9	C10—C15—H15A	109.5
C6—C5—H5	119.9	C10—C15—H15B	109.5
C5—C6—C7	119.2 (2)	C10—C15—H15C	109.5
C5—C6—H6	120.4	C10—C15—H15D	109.5
C7—C6—H6	120.4	C10—C15—H15E	109.5
C6—C7—C2	120.94 (19)	H15D—C15—H15E	109.5
C6—C7—H7	119.5	C10—C15—H15F	109.5
C2—C7—H7	119.5	H15D—C15—H15F	109.5
C9—C8—C13	119.91 (14)	H15E—C15—H15F	109.5
C9—C8—N1	123.04 (14)	C12—C16—H16A	109.5
C13—C8—N1	117.00 (13)	C12—C16—H16B	109.5
C8—C9—C10	119.92 (15)	C12—C16—H16C	109.5
C8—C9—H9	120	C12—C16—H16D	109.5
C10—C9—H9	120	C12—C16—H16E	109.5
C11—C10—C9	118.94 (15)	H16D—C16—H16E	109.5
C11—C10—C15	121.33 (16)	C12—C16—H16F	109.5
C9—C10—C15	119.71 (17)	H16D—C16—H16F	109.5
C10—C11—C12	122.04 (15)	H16E—C16—H16F	109.5
C10—C11—H11	119	C1—N1—C8	127.92 (12)
C12—C11—H11	119	C1—N1—H1N	116
C13—C12—C11	118.16 (15)	C8—N1—H1N	116
C13—C12—C16	121.09 (16)
O1—C1—C2—C7	136.94 (16)	N1—C8—C9—C10	−177.47 (13)
N1—C1—C2—C7	−42.4 (2)	C8—C9—C10—C11	−0.7 (2)
O1—C1—C2—C3	−41.5 (2)	C8—C9—C10—C15	177.92 (15)
N1—C1—C2—C3	139.08 (15)	C9—C10—C11—C12	1.2 (2)
C7—C2—C3—C4	0.7 (3)	C15—C10—C11—C12	−177.41 (16)
C1—C2—C3—C4	179.16 (17)	C10—C11—C12—C13	−0.9 (2)
C7—C2—C3—C14	178.64 (19)	C10—C11—C12—C16	178.48 (16)
C1—C2—C3—C14	−2.9 (3)	C11—C12—C13—C8	0.1 (2)
C2—C3—C4—C5	0.4 (3)	C16—C12—C13—C8	−179.26 (15)
C14—C3—C4—C5	−177.6 (2)	C9—C8—C13—C12	0.3 (2)
C3—C4—C5—C6	−0.7 (4)	N1—C8—C13—C12	177.91 (13)
C4—C5—C6—C7	−0.1 (4)	O1—C1—N1—C8	−3.4 (2)
C5—C6—C7—C2	1.2 (3)	C2—C1—N1—C8	176.00 (14)
C3—C2—C7—C6	−1.5 (3)	C9—C8—N1—C1	−27.9 (2)
C1—C2—C7—C6	−179.97 (18)	C13—C8—N1—C1	154.64 (15)
C13—C8—C9—C10	0.0 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1i	0.86	2.06	2.8935 (16)	163

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1i	0.86	2.06	2.8935 (16)	163

Symmetry code: (i) .