N,N'-Bis(3-methyl-phen-yl)propane-diamide.

The mol-ecular structure of the title compound, C(17)H(18)N(2)O(2), is symmetrical around the central C atom. The two halves of the mol-ecule are related by a twofold rotation axis. In each half of the mol-ecule, the structure is stabilized by intra-molecular C-H⋯O hydrogen bonds. Furthermore, each amide group is almost coplanar with the adjacent benzene ring [dihedral angle is 9.2 (2)°]. The planes of the amide groups are inclined at an angle of 68.5 (1)°, while the two benzene rings make a dihedral angle of 70.40 (3)°. In the crystal, mol-ecules are linked by inter-molecular N-H⋯O hydrogen bonds into chains running along the c axis. Neighbouring chains are weakly coupled by π-π stacking inter-actions [centroid-centroid distance = 3.7952 (8) Å].

Related literature

For related compounds, see: Gowda et al. (2007 ▶, 2009 ▶, 2010 ▶).

Experimental

Crystal data

C17H18N2O2

M = 282.33

Monoclinic,

a = 15.3617 (6) Å

b = 11.2277 (6) Å

c = 8.7316 (5) Å

β = 90.370 (4)°

V = 1505.97 (13) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 295 K

0.58 × 0.27 × 0.16 mm

Data collection

Oxford Diffraction Gemini R CCD diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009 ▶) T min = 0.970, T max = 0.989

11578 measured reflections

1457 independent reflections

1252 reflections with I > 2σ(I)

R int = 0.019

Refinement

R[F 2 > 2σ(F 2)] = 0.032

wR(F 2) = 0.096

S = 1.05

1457 reflections

101 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.15 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/S1600536810044089/bq2245sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810044089/bq2245Isup2.hkl

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

C17H18N2O2	F(000) = 600
Mr = 282.33	Dx = 1.245 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 7458 reflections
a = 15.3617 (6) Å	θ = 3.5–29.5°
b = 11.2277 (6) Å	µ = 0.08 mm−1
c = 8.7316 (5) Å	T = 295 K
β = 90.370 (4)°	Prism, colorless
V = 1505.97 (13) Å3	0.58 × 0.27 × 0.16 mm
Z = 4

Oxford Diffraction Gemini R CCD diffractometer	1457 independent reflections
graphite	1252 reflections with I > 2σ(I)
Detector resolution: 10.434 pixels mm-1	Rint = 0.019
ω scans	θmax = 25.8°, θmin = 3.2°
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	h = −18→18
Tmin = 0.970, Tmax = 0.989	k = −13→13
11578 measured reflections	l = −10→10

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)] = 0.032	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.096	w = 1/[σ2(Fo2) + (0.0517P)2 + 0.487P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max < 0.001
1457 reflections	Δρmax = 0.15 e Å−3
101 parameters	Δρmin = −0.13 e Å−3
1 restraint	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.017 (2)

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	Occ. (<1)
C1	0.27806 (7)	0.38760 (10)	0.16427 (12)	0.0365 (3)
C2	0.22710 (7)	0.41256 (11)	0.03724 (13)	0.0419 (3)
H2	0.2498	0.4597	−0.0404	0.05*
C3	0.14287 (8)	0.36894 (12)	0.02273 (14)	0.0475 (3)
C4	0.11069 (8)	0.29958 (13)	0.14029 (16)	0.0559 (4)
H4	0.0542	0.27	0.1339	0.067*
C5	0.16120 (9)	0.27374 (14)	0.26661 (16)	0.0583 (4)
H5	0.1383	0.2268	0.3443	0.07*
C6	0.24561 (8)	0.31628 (12)	0.28041 (13)	0.0478 (3)
H6	0.2797	0.2975	0.3655	0.057*
C7	0.42002 (7)	0.44614 (9)	0.28233 (11)	0.0334 (3)
C8	0.5	0.52114 (14)	0.25	0.0364 (4)
H8	0.4902 (8)	0.5697 (12)	0.1602 (13)	0.044*
C9	0.08888 (10)	0.39539 (16)	−0.11743 (19)	0.0696 (5)
H9A	0.107	0.4699	−0.1608	0.104*	0.5
H9B	0.0286	0.4002	−0.0897	0.104*	0.5
H9C	0.0966	0.333	−0.1913	0.104*	0.5
H9D	0.0478	0.3322	−0.1337	0.104*	0.5
H9E	0.1262	0.4019	−0.2048	0.104*	0.5
H9F	0.0582	0.469	−0.1032	0.104*	0.5
N1	0.36255 (6)	0.43945 (9)	0.16717 (10)	0.0382 (3)
H1N	0.379	0.4711	0.0825	0.046*
O1	0.41040 (5)	0.39905 (8)	0.40829 (8)	0.0475 (3)

	U11	U22	U33	U12	U13	U23
C1	0.0337 (6)	0.0422 (6)	0.0337 (5)	−0.0052 (4)	−0.0007 (4)	−0.0028 (4)
C2	0.0378 (6)	0.0485 (7)	0.0394 (6)	−0.0059 (5)	−0.0026 (5)	0.0048 (5)
C3	0.0382 (6)	0.0509 (7)	0.0532 (7)	−0.0035 (5)	−0.0085 (5)	−0.0028 (6)
C4	0.0394 (7)	0.0619 (8)	0.0663 (8)	−0.0177 (6)	−0.0014 (6)	−0.0012 (7)
C5	0.0561 (8)	0.0647 (9)	0.0541 (8)	−0.0246 (7)	0.0036 (6)	0.0089 (6)
C6	0.0487 (7)	0.0555 (7)	0.0390 (6)	−0.0129 (6)	−0.0034 (5)	0.0060 (5)
C7	0.0326 (6)	0.0384 (6)	0.0292 (5)	0.0024 (4)	−0.0010 (4)	−0.0029 (4)
C8	0.0322 (8)	0.0390 (8)	0.0380 (8)	0	−0.0048 (6)	0
C9	0.0491 (8)	0.0836 (11)	0.0758 (10)	−0.0062 (7)	−0.0254 (7)	0.0075 (8)
N1	0.0341 (5)	0.0513 (6)	0.0292 (5)	−0.0086 (4)	−0.0016 (4)	0.0051 (4)
O1	0.0478 (5)	0.0633 (6)	0.0313 (4)	−0.0085 (4)	−0.0044 (3)	0.0060 (4)

C1—C2	1.3821 (16)	C7—O1	1.2301 (13)
C1—C6	1.3873 (16)	C7—N1	1.3359 (14)
C1—N1	1.4226 (14)	C7—C8	1.5176 (14)
C2—C3	1.3886 (16)	C8—C7i	1.5176 (14)
C2—H2	0.93	C8—H8	0.966 (12)
C3—C4	1.3824 (19)	C9—H9A	0.96
C3—C9	1.5035 (18)	C9—H9B	0.96
C4—C5	1.3754 (19)	C9—H9C	0.96
C4—H4	0.93	C9—H9D	0.96
C5—C6	1.3863 (17)	C9—H9E	0.96
C5—H5	0.93	C9—H9F	0.96
C6—H6	0.93	N1—H1N	0.86
C2—C1—C6	119.96 (10)	C3—C9—H9A	109.5
C2—C1—N1	116.31 (10)	C3—C9—H9B	109.5
C6—C1—N1	123.73 (10)	H9A—C9—H9B	109.5
C1—C2—C3	121.62 (11)	C3—C9—H9C	109.5
C1—C2—H2	119.2	H9A—C9—H9C	109.5
C3—C2—H2	119.2	H9B—C9—H9C	109.5
C4—C3—C2	117.93 (11)	C3—C9—H9D	109.5
C4—C3—C9	121.18 (12)	H9A—C9—H9D	141.1
C2—C3—C9	120.89 (12)	H9B—C9—H9D	56.3
C5—C4—C3	120.78 (11)	H9C—C9—H9D	56.3
C5—C4—H4	119.6	C3—C9—H9E	109.5
C3—C4—H4	119.6	H9A—C9—H9E	56.3
C4—C5—C6	121.30 (12)	H9B—C9—H9E	141.1
C4—C5—H5	119.3	H9C—C9—H9E	56.3
C6—C5—H5	119.3	H9D—C9—H9E	109.5
C5—C6—C1	118.40 (11)	C3—C9—H9F	109.5
C5—C6—H6	120.8	H9A—C9—H9F	56.3
C1—C6—H6	120.8	H9B—C9—H9F	56.3
O1—C7—N1	124.49 (10)	H9C—C9—H9F	141.1
O1—C7—C8	120.45 (8)	H9D—C9—H9F	109.5
N1—C7—C8	115.03 (8)	H9E—C9—H9F	109.5
C7—C8—C7i	112.59 (13)	C7—N1—C1	129.41 (9)
C7—C8—H8	110.0 (7)	C7—N1—H1N	115.3
C7i—C8—H8	106.5 (7)	C1—N1—H1N	115.3
C6—C1—C2—C3	0.73 (19)	C2—C1—C6—C5	−1.35 (19)
N1—C1—C2—C3	−178.75 (11)	N1—C1—C6—C5	178.09 (12)
C1—C2—C3—C4	0.32 (19)	O1—C7—C8—C7i	78.05 (10)
C1—C2—C3—C9	−179.02 (13)	N1—C7—C8—C7i	−103.70 (9)
C2—C3—C4—C5	−0.7 (2)	O1—C7—N1—C1	5.17 (19)
C9—C3—C4—C5	178.61 (15)	C8—C7—N1—C1	−173.01 (11)
C3—C4—C5—C6	0.1 (2)	C2—C1—N1—C7	168.77 (11)
C4—C5—C6—C1	0.9 (2)	C6—C1—N1—C7	−10.69 (19)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O1	0.93	2.34	2.9124 (14)	120
N1—H1N···O1ii	0.86	2.16	2.9932 (12)	162
C8—H8···O1ii	0.97 (1)	2.54 (1)	3.3981 (9)	149 (1)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯O1	0.93	2.34	2.9124 (14)	120
N1—H1N⋯O1i	0.86	2.16	2.9932 (12)	162
C8—H8⋯O1i	0.97 (1)	2.54 (1)	3.3981 (9)	149 (1)

Symmetry code: (i) .