N-(3,5-Dimethyl-phen-yl)-4-methyl-benzamide.

In the title compound, C(16)H(17)NO, the dihedral angle between the two benzene rings is 16.6 (1)°. The crystal structure is stabilized by inter-molecular N-H⋯O hydrogen bonds, which link the mol-ecules into chains running along the c axis.

Related literature

For the preparation of the title compound, see: Gowda et al. (2003 ▶). For our studies on the effects of substituents on the structures and other aspects of N-(ar­yl)-amides, see: Bhat & Gowda (2000 ▶); Bowes et al. (2003 ▶); Gowda et al. (2009 ▶); Saeed et al. (2010 ▶), on N-(ar­yl)-methane­sulfonamides, see: Gowda et al. (2007 ▶), on N-(ar­yl)-aryl­sulfonamides, see: Shetty & Gowda (2005 ▶) and on N-chloro-aryl­amides, see: Gowda & Weiss (1994 ▶).

Experimental

Crystal data

C16H17NO

M = 239.31

Monoclinic,

a = 15.9048 (6) Å

b = 9.0323 (4) Å

c = 9.6774 (3) Å

β = 93.619 (3)°

V = 1387.45 (9) Å3

Z = 4

Mo Kα radiation

μ = 0.07 mm−1

T = 293 K

0.85 × 0.22 × 0.10 mm

Data collection

Oxford Diffraction Xcalibur Ruby Gemini diffractometer

Absorption correction: analytical [CrysAlis RED (Oxford Diffraction, 2009 ▶) based on expressions derived (Clark & Reid, 1995 ▶)] T min = 0.981, T max = 0.993

24108 measured reflections

3853 independent reflections

1720 reflections with I > 2σ(I)

R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.143

S = 0.95

3853 reflections

160 parameters

H-atom parameters constrained

Δρmax = 0.16 e Å−3

Δρmin = −0.17 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/S1600536811044904/bt5690sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811044904/bt5690Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811044904/bt5690Isup3.cml

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

C16H17NO	F(000) = 512
Mr = 239.31	Dx = 1.146 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9180 reflections
a = 15.9048 (6) Å	θ = 3.4–29.5°
b = 9.0323 (4) Å	µ = 0.07 mm−1
c = 9.6774 (3) Å	T = 293 K
β = 93.619 (3)°	Rod, colorless
V = 1387.45 (9) Å3	0.85 × 0.22 × 0.10 mm
Z = 4

Oxford Diffraction Xcalibur Ruby Gemini diffractometer	3853 independent reflections
Radiation source: Enhance (Mo) X-ray Source	1720 reflections with I > 2σ(I)
graphite	Rint = 0.029
Detector resolution: 10.4340 pixels mm-1	θmax = 29.5°, θmin = 3.4°
ω scans	h = −22→22
Absorption correction: analytical [CrysAlis RED (Oxford Diffraction, 2009) based on expressions derived (Clark & Reid, 1995)]	k = −12→12
Tmin = 0.981, Tmax = 0.993	l = −13→13
24108 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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.143	H-atom parameters constrained
S = 0.95	w = 1/[σ2(Fo2) + (0.0807P)2] where P = (Fo2 + 2Fc2)/3
3853 reflections	(Δ/σ)max < 0.001
160 parameters	Δρmax = 0.16 e Å−3
0 restraints	Δρmin = −0.17 e Å−3

Experimental. CrysAlis RED (Oxford Diffraction, 2009) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived (Clark & Reid, 1995).

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	0.10384 (9)	0.72822 (17)	0.65724 (13)	0.0516 (4)
C2	0.01648 (9)	0.69750 (16)	0.60172 (12)	0.0490 (4)
C3	−0.02569 (10)	0.78306 (18)	0.50007 (14)	0.0597 (4)
H3A	0.0010	0.8648	0.4641	0.072*
C4	−0.10664 (10)	0.7479 (2)	0.45208 (15)	0.0662 (5)
H4A	−0.1335	0.8063	0.3835	0.079*
C5	−0.14900 (9)	0.62795 (19)	0.50320 (14)	0.0589 (4)
C6	−0.10688 (10)	0.54526 (18)	0.60578 (13)	0.0590 (4)
H6A	−0.1340	0.4647	0.6430	0.071*
C7	−0.02621 (10)	0.57839 (17)	0.65440 (12)	0.0558 (4)
H7A	0.0002	0.5202	0.7236	0.067*
C8	−0.23550 (11)	0.5858 (2)	0.44574 (19)	0.0857 (6)
H8C	−0.2670	0.5457	0.5184	0.103*
H8B	−0.2311	0.5128	0.3744	0.103*
H8A	−0.2638	0.6719	0.4076	0.103*
C9	0.23454 (9)	0.86647 (18)	0.60272 (13)	0.0554 (4)
C10	0.26402 (10)	0.96307 (18)	0.50518 (14)	0.0620 (4)
H10A	0.2297	0.9857	0.4266	0.074*
C11	0.34300 (10)	1.0264 (2)	0.52210 (16)	0.0705 (5)
C12	0.39208 (11)	0.9929 (2)	0.64150 (19)	0.0800 (5)
H12A	0.4448	1.0367	0.6557	0.096*
C13	0.36468 (11)	0.8959 (2)	0.74052 (16)	0.0737 (5)
C14	0.28568 (10)	0.8325 (2)	0.72012 (14)	0.0652 (5)
H14A	0.2667	0.7669	0.7853	0.078*
C15	0.37495 (9)	1.12687 (19)	0.41307 (14)	0.1005 (7)
H15C	0.4201	1.1866	0.4531	0.121*
H15B	0.3300	1.1898	0.3773	0.121*
H15A	0.3951	1.0684	0.3392	0.121*
C16	0.41977 (9)	0.86018 (19)	0.86910 (14)	0.1075 (8)
H16C	0.3865	0.8133	0.9360	0.129*
H16B	0.4437	0.9499	0.9075	0.129*
H16A	0.4642	0.7946	0.8456	0.129*
N1	0.15225 (8)	0.80933 (14)	0.57539 (11)	0.0572 (4)
H1A	0.1296	0.8292	0.4945	0.069*
O1	0.12997 (7)	0.68252 (12)	0.77180 (8)	0.0649 (3)

	U11	U22	U33	U12	U13	U23
C1	0.0602 (9)	0.0549 (9)	0.0394 (7)	0.0012 (7)	0.0015 (6)	−0.0079 (6)
C2	0.0573 (9)	0.0507 (9)	0.0391 (7)	−0.0011 (7)	0.0039 (6)	−0.0056 (6)
C3	0.0602 (10)	0.0559 (10)	0.0628 (8)	−0.0039 (8)	0.0028 (7)	0.0083 (7)
C4	0.0598 (11)	0.0686 (11)	0.0693 (9)	0.0056 (9)	−0.0036 (8)	0.0113 (8)
C5	0.0544 (10)	0.0634 (11)	0.0592 (8)	−0.0015 (8)	0.0053 (7)	−0.0083 (7)
C6	0.0674 (10)	0.0561 (10)	0.0542 (8)	−0.0110 (8)	0.0095 (7)	−0.0034 (7)
C7	0.0688 (10)	0.0558 (10)	0.0424 (7)	−0.0017 (8)	0.0013 (6)	−0.0001 (6)
C8	0.0639 (12)	0.0939 (15)	0.0983 (12)	−0.0037 (10)	−0.0028 (9)	−0.0059 (11)
C9	0.0508 (9)	0.0620 (10)	0.0531 (8)	−0.0002 (7)	0.0005 (6)	−0.0116 (7)
C10	0.0567 (10)	0.0700 (11)	0.0592 (8)	−0.0028 (8)	0.0030 (7)	−0.0077 (7)
C11	0.0590 (11)	0.0728 (12)	0.0800 (10)	−0.0053 (9)	0.0074 (8)	−0.0072 (9)
C12	0.0520 (10)	0.0856 (14)	0.1017 (13)	−0.0087 (10)	−0.0009 (9)	−0.0170 (11)
C13	0.0562 (11)	0.0865 (14)	0.0767 (10)	0.0031 (9)	−0.0097 (8)	−0.0090 (9)
C14	0.0578 (10)	0.0753 (12)	0.0613 (9)	−0.0011 (8)	−0.0050 (7)	−0.0032 (7)
C15	0.0800 (14)	0.1071 (18)	0.1156 (14)	−0.0235 (12)	0.0155 (11)	0.0103 (13)
C16	0.0702 (13)	0.141 (2)	0.1072 (14)	−0.0027 (13)	−0.0314 (11)	0.0019 (13)
N1	0.0568 (8)	0.0726 (9)	0.0415 (6)	−0.0092 (7)	−0.0036 (5)	0.0006 (5)
O1	0.0700 (7)	0.0809 (8)	0.0428 (6)	−0.0007 (6)	−0.0041 (5)	0.0038 (5)

C1—O1	1.2305 (15)	C9—C14	1.389 (2)
C1—N1	1.3542 (18)	C9—N1	1.4162 (18)
C1—C2	1.484 (2)	C10—C11	1.380 (2)
C2—C7	1.386 (2)	C10—H10A	0.9300
C2—C3	1.3898 (19)	C11—C12	1.386 (2)
C3—C4	1.378 (2)	C11—C15	1.504 (2)
C3—H3A	0.9300	C12—C13	1.389 (2)
C4—C5	1.384 (2)	C12—H12A	0.9300
C4—H4A	0.9300	C13—C14	1.383 (2)
C5—C6	1.381 (2)	C13—C16	1.511 (2)
C5—C8	1.500 (2)	C14—H14A	0.9300
C6—C7	1.372 (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—C10	1.388 (2)	N1—H1A	0.8600
O1—C1—N1	122.44 (13)	C11—C10—C9	121.56 (14)
O1—C1—C2	121.25 (13)	C11—C10—H10A	119.2
N1—C1—C2	116.32 (12)	C9—C10—H10A	119.2
C7—C2—C3	117.78 (14)	C10—C11—C12	117.97 (16)
C7—C2—C1	118.76 (13)	C10—C11—C15	120.79 (14)
C3—C2—C1	123.46 (13)	C12—C11—C15	121.24 (15)
C4—C3—C2	120.62 (15)	C11—C12—C13	121.86 (16)
C4—C3—H3A	119.7	C11—C12—H12A	119.1
C2—C3—H3A	119.7	C13—C12—H12A	119.1
C3—C4—C5	121.71 (14)	C14—C13—C12	118.96 (15)
C3—C4—H4A	119.1	C14—C13—C16	120.24 (16)
C5—C4—H4A	119.1	C12—C13—C16	120.80 (15)
C6—C5—C4	117.08 (14)	C13—C14—C9	120.34 (16)
C6—C5—C8	121.40 (16)	C13—C14—H14A	119.8
C4—C5—C8	121.47 (15)	C9—C14—H14A	119.8
C7—C6—C5	121.96 (15)	C11—C15—H15C	109.5
C7—C6—H6A	119.0	C11—C15—H15B	109.5
C5—C6—H6A	119.0	H15C—C15—H15B	109.5
C6—C7—C2	120.83 (14)	C11—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	C13—C16—H16C	109.5
C5—C8—H8B	109.5	C13—C16—H16B	109.5
H8C—C8—H8B	109.5	H16C—C16—H16B	109.5
C5—C8—H8A	109.5	C13—C16—H16A	109.5
H8C—C8—H8A	109.5	H16C—C16—H16A	109.5
H8B—C8—H8A	109.5	H16B—C16—H16A	109.5
C10—C9—C14	119.29 (14)	C1—N1—C9	129.85 (12)
C10—C9—N1	116.73 (12)	C1—N1—H1A	115.1
C14—C9—N1	123.98 (14)	C9—N1—H1A	115.1
O1—C1—C2—C7	−21.8 (2)	N1—C9—C10—C11	179.38 (14)
N1—C1—C2—C7	158.54 (12)	C9—C10—C11—C12	−1.2 (2)
O1—C1—C2—C3	157.45 (13)	C9—C10—C11—C15	177.99 (14)
N1—C1—C2—C3	−22.2 (2)	C10—C11—C12—C13	1.7 (3)
C7—C2—C3—C4	−1.3 (2)	C15—C11—C12—C13	−177.49 (17)
C1—C2—C3—C4	179.48 (13)	C11—C12—C13—C14	−0.9 (3)
C2—C3—C4—C5	0.5 (2)	C11—C12—C13—C16	179.40 (16)
C3—C4—C5—C6	0.6 (2)	C12—C13—C14—C9	−0.4 (3)
C3—C4—C5—C8	−176.97 (15)	C16—C13—C14—C9	179.28 (14)
C4—C5—C6—C7	−0.8 (2)	C10—C9—C14—C13	0.9 (2)
C8—C5—C6—C7	176.75 (14)	N1—C9—C14—C13	−178.51 (14)
C5—C6—C7—C2	0.0 (2)	O1—C1—N1—C9	−5.2 (2)
C3—C2—C7—C6	1.0 (2)	C2—C1—N1—C9	174.40 (13)
C1—C2—C7—C6	−179.66 (12)	C10—C9—N1—C1	−171.53 (14)
C14—C9—C10—C11	0.0 (2)	C14—C9—N1—C1	7.9 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1i	0.86	2.16	2.9379 (13)	151.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O1i	0.86	2.16	2.9379 (13)	151

Symmetry code: (i) .