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

In the title compound, C(16)H(17)NO, the two aromatic rings are almost coplanar, making a dihedral angle of 1.9 (2)°. The amide group makes dihedral angles of 48.0 (3) and 48.6 (3)° with the 2-methyl-phenyl and the 2,5-dimethyl-phenyl rings, respectively. Inter-molecular N-H⋯O hydrogen bonds link the mol-ecules into chains running along the a axis of the crystal.

Related literature

For related structures, see Gowda, Foro et al. (2008 ▶); Gowda, Tokarčík et al. (2009 ▶).

Experimental

Crystal data

C16H17NO

M = 239.31

Orthorhombic,

a = 4.90104 (10) Å

b = 5.85657 (16) Å

c = 45.8291 (12) Å

V = 1315.45 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 295 K

0.54 × 0.35 × 0.09 mm

Data collection

Oxford Diffraction Xcalibur Ruby Gemini diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009 ▶) T min = 0.957, T max = 0.990

22131 measured reflections

1414 independent reflections

1338 reflections with I > 2σ(I)

R int = 0.037

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.097

S = 1.20

1414 reflections

165 parameters

H-atom parameters constrained

Δρmax = 0.12 e Å−3

Δρmin = −0.13 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/S160053681000886X/dn2545sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681000886X/dn2545Isup2.hkl

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

C16H17NO	F(000) = 512
Mr = 239.31	Dx = 1.208 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 11414 reflections
a = 4.90104 (10) Å	θ = 1.8–29.5°
b = 5.85657 (16) Å	µ = 0.08 mm−1
c = 45.8291 (12) Å	T = 295 K
V = 1315.45 (6) Å3	Block, colourless
Z = 4	0.54 × 0.35 × 0.09 mm

Oxford Diffraction Xcalibur Ruby Gemini diffractometer	1414 independent reflections
graphite	1338 reflections with I > 2σ(I)
Detector resolution: 10.434 pixels mm-1	Rint = 0.037
ω scans	θmax = 25°, θmin = 1.8°
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	h = −5→5
Tmin = 0.957, Tmax = 0.990	k = −6→6
22131 measured reflections	l = −54→54

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.097	H-atom parameters constrained
S = 1.20	w = 1/[σ2(Fo2) + (0.0248P)2 + 0.5849P] where P = (Fo2 + 2Fc2)/3
1414 reflections	(Δ/σ)max < 0.001
165 parameters	Δρmax = 0.12 e Å−3
0 restraints	Δρmin = −0.13 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)
O1	0.1938 (4)	0.2752 (5)	0.11488 (4)	0.0571 (7)
N1	0.6250 (4)	0.2075 (4)	0.12991 (4)	0.0354 (5)
H1N	0.7945	0.2132	0.1251	0.043*
C1	0.4388 (5)	0.2701 (5)	0.10975 (5)	0.0345 (6)
C2	0.5509 (5)	0.3297 (5)	0.08026 (5)	0.0340 (6)
C3	0.4651 (6)	0.5263 (5)	0.06577 (6)	0.0436 (7)
C4	0.5758 (7)	0.5680 (6)	0.03829 (6)	0.0580 (9)
H4	0.5241	0.6989	0.0282	0.070*
C5	0.7593 (7)	0.4208 (7)	0.02570 (6)	0.0644 (10)
H5	0.8294	0.4532	0.0073	0.077*
C6	0.8400 (7)	0.2271 (7)	0.03994 (6)	0.0600 (9)
H6	0.9627	0.1267	0.0313	0.072*
C7	0.7366 (6)	0.1831 (5)	0.06728 (6)	0.0446 (7)
H7	0.7924	0.0528	0.0772	0.054*
C8	0.5574 (5)	0.1322 (4)	0.15873 (5)	0.0323 (6)
C9	0.6678 (6)	−0.0703 (5)	0.16930 (6)	0.0382 (6)
C10	0.5923 (6)	−0.1364 (5)	0.19709 (6)	0.0484 (8)
H10	0.6660	−0.2696	0.2048	0.058*
C11	0.4121 (6)	−0.0122 (5)	0.21371 (6)	0.0488 (8)
H11	0.3631	−0.0644	0.2321	0.059*
C12	0.3027 (6)	0.1906 (5)	0.20322 (5)	0.0399 (7)
C13	0.3794 (5)	0.2610 (5)	0.17554 (5)	0.0365 (6)
H13	0.3103	0.3969	0.1681	0.044*
C14	0.2646 (7)	0.6906 (6)	0.07875 (8)	0.0633 (9)
H14A	0.2576	0.8264	0.0670	0.095*
H14B	0.3206	0.7294	0.0982	0.095*
H14C	0.0872	0.6213	0.0793	0.095*
C15	0.8619 (6)	−0.2117 (5)	0.15136 (6)	0.0527 (8)
H15A	1.0349	−0.1354	0.1502	0.079*
H15B	0.7888	−0.2316	0.1321	0.079*
H15C	0.8857	−0.3583	0.1604	0.079*
C16	0.1035 (7)	0.3287 (6)	0.22091 (6)	0.0566 (9)
H16A	0.1199	0.2888	0.2412	0.068*	0.74
H16B	−0.0786	0.2971	0.2144	0.068*	0.74
H16C	0.1420	0.4883	0.2185	0.068*	0.74
H16D	0.0025	0.4276	0.2082	0.068*	0.26
H16E	0.2007	0.4188	0.2350	0.068*	0.26
H16F	−0.0201	0.2279	0.2309	0.068*	0.26

	U11	U22	U33	U12	U13	U23
O1	0.0242 (10)	0.0968 (18)	0.0502 (11)	0.0001 (13)	0.0046 (9)	0.0132 (13)
N1	0.0211 (10)	0.0470 (13)	0.0382 (11)	0.0021 (11)	0.0061 (9)	0.0045 (11)
C1	0.0267 (13)	0.0385 (15)	0.0382 (14)	−0.0019 (13)	0.0028 (11)	−0.0007 (13)
C2	0.0242 (12)	0.0429 (15)	0.0349 (13)	−0.0036 (13)	−0.0003 (11)	−0.0024 (12)
C3	0.0354 (15)	0.0501 (17)	0.0454 (16)	−0.0044 (15)	−0.0066 (13)	0.0029 (14)
C4	0.058 (2)	0.068 (2)	0.0477 (17)	−0.005 (2)	−0.0123 (17)	0.0192 (17)
C5	0.059 (2)	0.100 (3)	0.0339 (15)	−0.011 (2)	0.0050 (15)	0.0039 (19)
C6	0.0532 (19)	0.084 (2)	0.0424 (16)	0.005 (2)	0.0094 (15)	−0.0104 (18)
C7	0.0376 (15)	0.0532 (18)	0.0431 (15)	0.0033 (16)	0.0023 (13)	−0.0010 (14)
C8	0.0271 (13)	0.0359 (14)	0.0340 (13)	−0.0028 (13)	0.0029 (12)	0.0016 (11)
C9	0.0315 (14)	0.0402 (15)	0.0429 (15)	−0.0003 (14)	0.0006 (12)	0.0004 (12)
C10	0.0488 (17)	0.0452 (17)	0.0511 (17)	0.0070 (17)	0.0016 (15)	0.0145 (14)
C11	0.0489 (18)	0.0584 (19)	0.0392 (15)	0.0001 (18)	0.0067 (15)	0.0120 (15)
C12	0.0337 (14)	0.0497 (17)	0.0363 (13)	−0.0020 (15)	0.0046 (12)	−0.0020 (13)
C13	0.0331 (13)	0.0369 (14)	0.0395 (14)	0.0044 (14)	0.0022 (11)	0.0016 (12)
C14	0.0526 (19)	0.0535 (19)	0.084 (2)	0.0100 (19)	−0.0045 (18)	0.0053 (19)
C15	0.0522 (18)	0.0435 (17)	0.0625 (18)	0.0149 (18)	0.0056 (15)	0.0020 (15)
C16	0.0529 (19)	0.072 (2)	0.0449 (16)	0.007 (2)	0.0120 (15)	−0.0044 (16)

O1—C1	1.224 (3)	C10—C11	1.375 (4)
N1—C1	1.349 (3)	C10—H10	0.9300
N1—C8	1.431 (3)	C11—C12	1.389 (4)
N1—H1N	0.8598	C11—H11	0.9300
C1—C2	1.500 (3)	C12—C13	1.386 (3)
C2—C7	1.386 (4)	C12—C16	1.505 (4)
C2—C3	1.394 (4)	C13—H13	0.9300
C3—C4	1.393 (4)	C14—H14A	0.9600
C3—C14	1.499 (4)	C14—H14B	0.9600
C4—C5	1.373 (5)	C14—H14C	0.9600
C4—H4	0.9300	C15—H15A	0.9600
C5—C6	1.367 (5)	C15—H15B	0.9600
C5—H5	0.9300	C15—H15C	0.9600
C6—C7	1.376 (4)	C16—H16A	0.9599
C6—H6	0.9300	C16—H16B	0.9598
C7—H7	0.9300	C16—H16C	0.9602
C8—C13	1.387 (3)	C16—H16D	0.9605
C8—C9	1.391 (4)	C16—H16E	0.9588
C9—C10	1.381 (4)	C16—H16F	0.9607
C9—C15	1.505 (4)
C1—N1—C8	124.0 (2)	C11—C12—C16	121.6 (3)
C1—N1—H1N	117.9	C12—C13—C8	121.2 (3)
C8—N1—H1N	118.1	C12—C13—H13	119.4
O1—C1—N1	122.6 (2)	C8—C13—H13	119.4
O1—C1—C2	121.8 (2)	C3—C14—H14A	109.5
N1—C1—C2	115.6 (2)	C3—C14—H14B	109.5
C7—C2—C3	120.4 (3)	H14A—C14—H14B	109.5
C7—C2—C1	118.9 (2)	C3—C14—H14C	109.5
C3—C2—C1	120.7 (2)	H14A—C14—H14C	109.5
C4—C3—C2	117.3 (3)	H14B—C14—H14C	109.5
C4—C3—C14	120.1 (3)	C9—C15—H15A	109.5
C2—C3—C14	122.6 (3)	C9—C15—H15B	109.5
C5—C4—C3	121.7 (3)	H15A—C15—H15B	109.5
C5—C4—H4	119.2	C9—C15—H15C	109.5
C3—C4—H4	119.2	H15A—C15—H15C	109.5
C6—C5—C4	120.7 (3)	H15B—C15—H15C	109.5
C6—C5—H5	119.7	C12—C16—H16A	109.6
C4—C5—H5	119.7	C12—C16—H16B	109.3
C5—C6—C7	118.9 (3)	H16A—C16—H16B	109.5
C5—C6—H6	120.5	C12—C16—H16C	109.4
C7—C6—H6	120.5	H16A—C16—H16C	109.5
C6—C7—C2	121.1 (3)	H16B—C16—H16C	109.5
C6—C7—H7	119.4	C12—C16—H16D	109.3
C2—C7—H7	119.4	H16A—C16—H16D	141.1
C13—C8—C9	121.0 (2)	H16B—C16—H16D	56.4
C13—C8—N1	119.4 (2)	H16C—C16—H16D	56.1
C9—C8—N1	119.6 (2)	C12—C16—H16E	109.6
C10—C9—C8	117.1 (3)	H16A—C16—H16E	56.2
C10—C9—C15	121.2 (3)	H16B—C16—H16E	141.1
C8—C9—C15	121.6 (2)	H16C—C16—H16E	56.3
C11—C10—C9	122.3 (3)	H16D—C16—H16E	109.4
C11—C10—H10	118.8	C12—C16—H16F	109.5
C9—C10—H10	118.8	H16A—C16—H16F	56.3
C10—C11—C12	120.6 (3)	H16B—C16—H16F	56.2
C10—C11—H11	119.7	H16C—C16—H16F	141.1
C12—C11—H11	119.7	H16D—C16—H16F	109.5
C13—C12—C11	117.8 (3)	H16E—C16—H16F	109.5
C13—C12—C16	120.6 (3)
C8—N1—C1—O1	2.7 (5)	C1—C2—C7—C6	178.3 (3)
C8—N1—C1—C2	−176.3 (2)	C1—N1—C8—C13	−49.7 (4)
O1—C1—C2—C7	−130.9 (3)	C1—N1—C8—C9	129.3 (3)
N1—C1—C2—C7	48.1 (3)	C13—C8—C9—C10	0.0 (4)
O1—C1—C2—C3	47.5 (4)	N1—C8—C9—C10	−179.1 (3)
N1—C1—C2—C3	−133.5 (3)	C13—C8—C9—C15	−179.8 (3)
C7—C2—C3—C4	−0.7 (4)	N1—C8—C9—C15	1.1 (4)
C1—C2—C3—C4	−179.1 (3)	C8—C9—C10—C11	1.3 (4)
C7—C2—C3—C14	180.0 (3)	C15—C9—C10—C11	−178.9 (3)
C1—C2—C3—C14	1.5 (4)	C9—C10—C11—C12	−1.6 (5)
C2—C3—C4—C5	0.8 (4)	C10—C11—C12—C13	0.6 (4)
C14—C3—C4—C5	−179.8 (3)	C10—C11—C12—C16	179.5 (3)
C3—C4—C5—C6	−0.1 (5)	C11—C12—C13—C8	0.6 (4)
C4—C5—C6—C7	−0.7 (5)	C16—C12—C13—C8	−178.3 (2)
C5—C6—C7—C2	0.9 (5)	C9—C8—C13—C12	−0.9 (4)
C3—C2—C7—C6	−0.2 (4)	N1—C8—C13—C12	178.1 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1i	0.86	2.05	2.899 (3)	172

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1i	0.86	2.05	2.899 (3)	172

Symmetry code: (i) .