N-(2,3-Dimethyl-phen-yl)-4-methylbenzamide.

In the mol-ecule of the title compound, C(16)H(17)NO, the two aromatic rings are almost perpendicular to each other [dihedral angle 85.90 (5)°]. The crystal structure is stabilized by inter-molecular N-H⋯O hydrogen bonds which link the mol-ecules, forming C(4) chains running along the c axis.

Related literature

For preparation of the title compound, see: Gowda et al. (2003 ▶). For the study of the effect of substituents on the structures and other aspects of N-(ar­yl)amides, see: Arjunan et al. (2004 ▶); Bhat & Gowda (2000 ▶); Bowes et al. (2003 ▶); Gowda et al. (2009 ▶); Rodrigues et al. (2011 ▶); Saeed et al. (2010 ▶).

Experimental

Crystal data

C16H17NO

M = 239.31

Monoclinic,

a = 8.1723 (3) Å

b = 19.3923 (7) Å

c = 9.3170 (3) Å

β = 111.781 (4)°

V = 1371.14 (9) Å3

Z = 4

Mo Kα radiation

μ = 0.07 mm−1

T = 293 K

0.76 × 0.12 × 0.09 mm

Data collection

Oxford Xcalibur Ruby Gemini diffractometer

Absorption correction: analytical [CrysAlis RED (Oxford Diffraction, 2009 ▶) based on Clark & Reid (1995 ▶)] T min = 0.989, T max = 0.994

21529 measured reflections

3806 independent reflections

1925 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.126

S = 0.93

3806 reflections

166 parameters

H-atom parameters constrained

Δρmax = 0.20 e Å−3

Δρmin = −0.18 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2009 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg, 2002 ▶); software used to prepare material for publication: enCIFer (Allen et al., 2004 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811034490/bt5622sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811034490/bt5622Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811034490/bt5622Isup3.cml

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

C16H17NO	F(000) = 512
Mr = 239.31	Dx = 1.159 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 7558 reflections
a = 8.1723 (3) Å	θ = 3.5–29.5°
b = 19.3923 (7) Å	µ = 0.07 mm−1
c = 9.3170 (3) Å	T = 293 K
β = 111.781 (4)°	Cuboid, colourless
V = 1371.14 (9) Å3	0.76 × 0.12 × 0.09 mm
Z = 4

Oxford Xcalibur Ruby Gemini diffractometer	3806 independent reflections
Radiation source: fine-focus sealed tube	1925 reflections with I > 2σ(I)
graphite	Rint = 0.030
Detector resolution: 10.4340 pixels mm-1	θmax = 29.5°, θmin = 3.5°
ω scans	h = −10→11
Absorption correction: analytical [CrysAlis RED (Oxford Diffraction, 2009). Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by Clark & Reid (1995).]	k = −24→26
Tmin = 0.989, Tmax = 0.994	l = −12→12
21529 measured reflections

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.126	H-atom parameters constrained
S = 0.93	w = 1/[σ2(Fo2) + (0.0738P)2] where P = (Fo2 + 2Fc2)/3
3806 reflections	(Δ/σ)max = 0.001
166 parameters	Δρmax = 0.20 e Å−3
0 restraints	Δρmin = −0.18 e Å−3

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	0.73885 (17)	0.70346 (6)	0.43887 (13)	0.0447 (3)
C2	0.84624 (17)	0.65196 (6)	0.39419 (13)	0.0440 (3)
C3	0.80527 (19)	0.62986 (7)	0.24275 (14)	0.0512 (3)
H3A	0.7064	0.6474	0.1642	0.061*
C4	0.9099 (2)	0.58240 (7)	0.20867 (15)	0.0572 (4)
H4A	0.8805	0.5684	0.1067	0.069*
C5	1.0570 (2)	0.55487 (7)	0.32099 (16)	0.0571 (4)
C6	1.0959 (2)	0.57579 (8)	0.47215 (17)	0.0613 (4)
H6A	1.1935	0.5573	0.5504	0.074*
C7	0.9927 (2)	0.62340 (7)	0.50858 (14)	0.0552 (4)
H7A	1.0213	0.6366	0.6110	0.066*
C8	1.1734 (3)	0.50369 (9)	0.2821 (2)	0.0863 (5)
H8C	1.2149	0.4698	0.3627	0.104*
H8B	1.2721	0.5274	0.2727	0.104*
H8A	1.1072	0.4813	0.1861	0.104*
C9	0.53294 (17)	0.79984 (6)	0.35140 (12)	0.0433 (3)
C10	0.38966 (17)	0.78287 (7)	0.39137 (13)	0.0476 (3)
C11	0.29061 (19)	0.83671 (9)	0.41903 (14)	0.0579 (4)
C12	0.3352 (2)	0.90411 (9)	0.40209 (17)	0.0671 (4)
H12A	0.2703	0.9397	0.4221	0.081*
C13	0.4729 (2)	0.92024 (8)	0.35643 (15)	0.0635 (4)
H13A	0.4983	0.9660	0.3431	0.076*
C14	0.57237 (19)	0.86776 (7)	0.33078 (14)	0.0519 (3)
H14A	0.6655	0.8779	0.2998	0.062*
C15	0.3376 (2)	0.70931 (8)	0.39997 (17)	0.0644 (4)
H15C	0.2119	0.7050	0.3519	0.077*
H15B	0.3751	0.6955	0.5063	0.077*
H15A	0.3926	0.6804	0.3473	0.077*
C16	0.1334 (2)	0.82157 (11)	0.4618 (2)	0.0875 (6)
H16C	0.0944	0.8634	0.4942	0.105*
H16B	0.1659	0.7887	0.5448	0.105*
H16A	0.0398	0.8030	0.3738	0.105*
N1	0.64148 (14)	0.74732 (5)	0.32655 (10)	0.0464 (3)
H1A	0.6453	0.7433	0.2359	0.056*
O1	0.74010 (13)	0.70534 (5)	0.57153 (9)	0.0590 (3)

	U11	U22	U33	U12	U13	U23
C1	0.0527 (8)	0.0490 (7)	0.0389 (6)	−0.0046 (6)	0.0246 (6)	−0.0015 (5)
C2	0.0533 (8)	0.0454 (7)	0.0388 (6)	−0.0039 (6)	0.0235 (6)	0.0006 (5)
C3	0.0606 (9)	0.0540 (8)	0.0424 (7)	0.0058 (7)	0.0229 (6)	−0.0014 (6)
C4	0.0755 (10)	0.0551 (8)	0.0476 (7)	0.0004 (7)	0.0306 (7)	−0.0053 (6)
C5	0.0686 (10)	0.0479 (8)	0.0666 (9)	0.0022 (7)	0.0387 (8)	0.0003 (6)
C6	0.0609 (9)	0.0601 (9)	0.0614 (8)	0.0103 (7)	0.0211 (7)	0.0072 (7)
C7	0.0664 (9)	0.0594 (9)	0.0411 (7)	0.0012 (7)	0.0215 (6)	0.0004 (6)
C8	0.0961 (13)	0.0766 (12)	0.1019 (13)	0.0218 (10)	0.0550 (11)	0.0016 (9)
C9	0.0481 (8)	0.0494 (8)	0.0337 (6)	−0.0015 (6)	0.0169 (5)	−0.0014 (5)
C10	0.0474 (8)	0.0599 (9)	0.0355 (6)	−0.0048 (6)	0.0154 (5)	−0.0020 (5)
C11	0.0486 (8)	0.0800 (11)	0.0440 (7)	0.0053 (8)	0.0159 (6)	−0.0056 (7)
C12	0.0661 (10)	0.0710 (11)	0.0602 (9)	0.0180 (8)	0.0186 (8)	−0.0097 (7)
C13	0.0714 (11)	0.0506 (8)	0.0600 (9)	0.0010 (8)	0.0145 (8)	−0.0013 (6)
C14	0.0550 (8)	0.0532 (8)	0.0473 (7)	−0.0053 (7)	0.0186 (6)	0.0015 (6)
C15	0.0630 (10)	0.0735 (10)	0.0602 (8)	−0.0178 (8)	0.0270 (7)	0.0017 (7)
C16	0.0647 (11)	0.1299 (16)	0.0789 (11)	0.0118 (11)	0.0395 (9)	−0.0020 (10)
N1	0.0596 (7)	0.0515 (6)	0.0367 (5)	0.0031 (5)	0.0277 (5)	0.0012 (4)
O1	0.0775 (7)	0.0704 (7)	0.0385 (5)	0.0099 (5)	0.0324 (5)	0.0019 (4)

C1—O1	1.2327 (13)	C9—C10	1.3935 (18)
C1—N1	1.3542 (16)	C9—N1	1.4248 (16)
C1—C2	1.4873 (17)	C10—C11	1.402 (2)
C2—C7	1.3885 (19)	C10—C15	1.4991 (19)
C2—C3	1.3913 (17)	C11—C12	1.381 (2)
C3—C4	1.3711 (19)	C11—C16	1.509 (2)
C3—H3A	0.9300	C12—C13	1.379 (2)
C4—C5	1.376 (2)	C12—H12A	0.9300
C4—H4A	0.9300	C13—C14	1.378 (2)
C5—C6	1.385 (2)	C13—H13A	0.9300
C5—C8	1.509 (2)	C14—H14A	0.9300
C6—C7	1.375 (2)	C15—H15C	0.9600
C6—H6A	0.9300	C15—H15B	0.9600
C7—H7A	0.9300	C15—H15A	0.9600
C8—H8C	0.9600	C16—H16C	0.9600
C8—H8B	0.9600	C16—H16B	0.9600
C8—H8A	0.9600	C16—H16A	0.9600
C9—C14	1.3861 (18)	N1—H1A	0.8600
O1—C1—N1	122.69 (12)	C9—C10—C11	118.22 (12)
O1—C1—C2	120.95 (11)	C9—C10—C15	121.48 (13)
N1—C1—C2	116.36 (10)	C11—C10—C15	120.27 (13)
C7—C2—C3	118.04 (12)	C12—C11—C10	119.27 (14)
C7—C2—C1	118.87 (10)	C12—C11—C16	120.03 (15)
C3—C2—C1	123.07 (12)	C10—C11—C16	120.67 (15)
C4—C3—C2	120.36 (13)	C13—C12—C11	121.99 (14)
C4—C3—H3A	119.8	C13—C12—H12A	119.0
C2—C3—H3A	119.8	C11—C12—H12A	119.0
C3—C4—C5	121.90 (12)	C14—C13—C12	119.20 (14)
C3—C4—H4A	119.0	C14—C13—H13A	120.4
C5—C4—H4A	119.0	C12—C13—H13A	120.4
C4—C5—C6	117.77 (13)	C13—C14—C9	119.69 (14)
C4—C5—C8	121.57 (13)	C13—C14—H14A	120.2
C6—C5—C8	120.66 (14)	C9—C14—H14A	120.2
C7—C6—C5	121.17 (13)	C10—C15—H15C	109.5
C7—C6—H6A	119.4	C10—C15—H15B	109.5
C5—C6—H6A	119.4	H15C—C15—H15B	109.5
C6—C7—C2	120.73 (12)	C10—C15—H15A	109.5
C6—C7—H7A	119.6	H15C—C15—H15A	109.5
C2—C7—H7A	119.6	H15B—C15—H15A	109.5
C5—C8—H8C	109.5	C11—C16—H16C	109.5
C5—C8—H8B	109.5	C11—C16—H16B	109.5
H8C—C8—H8B	109.5	H16C—C16—H16B	109.5
C5—C8—H8A	109.5	C11—C16—H16A	109.5
H8C—C8—H8A	109.5	H16C—C16—H16A	109.5
H8B—C8—H8A	109.5	H16B—C16—H16A	109.5
C14—C9—C10	121.54 (12)	C1—N1—C9	123.11 (9)
C14—C9—N1	117.78 (11)	C1—N1—H1A	118.4
C10—C9—N1	120.67 (11)	C9—N1—H1A	118.4
O1—C1—C2—C7	−23.19 (18)	C14—C9—C10—C15	174.52 (11)
N1—C1—C2—C7	156.80 (12)	N1—C9—C10—C15	−3.88 (17)
O1—C1—C2—C3	155.62 (13)	C9—C10—C11—C12	1.61 (17)
N1—C1—C2—C3	−24.40 (18)	C15—C10—C11—C12	−176.44 (12)
C7—C2—C3—C4	−1.4 (2)	C9—C10—C11—C16	179.66 (12)
C1—C2—C3—C4	179.75 (12)	C15—C10—C11—C16	1.61 (18)
C2—C3—C4—C5	0.2 (2)	C10—C11—C12—C13	1.0 (2)
C3—C4—C5—C6	1.0 (2)	C16—C11—C12—C13	−177.06 (14)
C3—C4—C5—C8	−178.80 (14)	C11—C12—C13—C14	−1.8 (2)
C4—C5—C6—C7	−1.1 (2)	C12—C13—C14—C9	−0.10 (19)
C8—C5—C6—C7	178.74 (15)	C10—C9—C14—C13	2.77 (17)
C5—C6—C7—C2	−0.1 (2)	N1—C9—C14—C13	−178.78 (11)
C3—C2—C7—C6	1.4 (2)	O1—C1—N1—C9	0.50 (19)
C1—C2—C7—C6	−179.77 (13)	C2—C1—N1—C9	−179.49 (10)
C14—C9—C10—C11	−3.50 (17)	C14—C9—N1—C1	118.12 (13)
N1—C9—C10—C11	178.09 (10)	C10—C9—N1—C1	−63.42 (16)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1i	0.86	2.20	2.9256 (12)	143.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O1i	0.86	2.20	2.9256 (12)	143

Symmetry code: (i) .