N,N,N′,N′-Tetra­methyl­phthalamide

Adel Hamada; Yamina Boudinar; Adel Beghidja; Mehdi Boutebdja

doi:10.1107/S1600536812035167

. 2012 Aug 15;68(Pt 9):o2710. doi: 10.1107/S1600536812035167

N,N,N′,N′-Tetramethylphthalamide

Adel Hamada ^a, Yamina Boudinar ^a, Adel Beghidja ^b,^*, Mehdi Boutebdja ^b

PMCID: PMC3435727 PMID: 22969598

Abstract

The title compound, C₁₂H₁₆N₂O₂, crystallized from toluene with two independent molecules in the asymmetric unit. The dihedral angles between the amide groups and the benzene ring are 60.87 (11) and 54.08 (11)° in one independent molecule and 60.13 (11) and 64.64 (11) in the other. The crystal structure features weak C—H⋯O hydrogen bonds and C—H⋯π interactions.

Related literature

For related structures, see: Altamura et al. (2005 ▶); Anderson et al. (2004 ▶); Clayden et al. (2001 ▶); Comins et al. (1998 ▶); Sakamoto et al. (2004 ▶).

Experimental

Crystal data

C₁₂H₁₆N₂O₂
M _r = 220.27
Monoclinic,
a = 6.7337 (6) Å
b = 18.1230 (14) Å
c = 9.8216 (8) Å
β = 104.918 (3)°
V = 1158.18 (17) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 100 K
0.56 × 0.52 × 0.33 mm

Data collection

Bruker APEXII diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2002 ▶) T _min = 0.925, T _max = 0.972
8205 measured reflections
2739 independent reflections
2414 reflections with I > 2σ(I)
R _int = 0.045

Refinement

R[F ² > 2σ(F ²)] = 0.049
wR(F ²) = 0.124
S = 1.06
2739 reflections
297 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.32 e Å⁻³
Δρ_min = −0.34 e Å⁻³

Data collection: APEX2 (Bruker, 2006 ▶); cell refinement: SAINT (Bruker, 2006 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ATOMS (Dowty, 1995 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812035167/bq2372sup1.cif

e-68-o2710-sup1.cif^{(37.8KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812035167/bq2372Isup2.hkl

e-68-o2710-Isup2.hkl^{(131.7KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812035167/bq2372Isup3.cml

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

Table 1. Hydrogen-bond geometry (Å, °).

Cg1 is the centroid of the C2–C7 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯O3ⁱ	0.93	2.60	3.518 (3)	170
C5—H5⋯O4ⁱⁱ	0.93	2.58	3.141 (4)	119
C6—H6⋯O4ⁱⁱ	0.93	2.51	3.105 (4)	122
C18—H18⋯O2ⁱⁱⁱ	0.93	2.49	3.329 (3)	150
C24—H24A⋯O2ⁱⁱⁱ	0.96	2.56	3.224 (4)	127
C16—H16⋯Cg1	0.93	2.97	3.810 (4)	124

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) .

Acknowledgments

The authors thank the MESRS (Algeria) for financial support.

supplementary crystallographic information

Comment

The molecular structure of (I) is composed of a two crystallographically independent molecules (IA and IB). A displacement ellipsoid plot of the two independent molecules of (I) is shown in Fig. 1. Bond lengths and angles in (I) are normal, and values for the two independent molecules agree with each other. The crystal structure of (I) is stabilized by intermolecular weak hydrogen-bonds type C—H···O (Fig. 2) and C—H··· π interactions, the latter interaction is observed between centroid of benzene ring (C2—C7) (IA) and hydrogen atom H16 of benzene ring (C14—C19) of the adjacent molecule (IB), with a Cg···H16 distance of 2.96 (2) Å (Fig. 1), resulting in the formation of infinite three-dimensional network reinforcing a cohesion of structure. Hydrogen-bonding parameters are listed in Table 1.

Experimental

To a suspension of phthalic acid (1 g, 6.02 mmol) in anhydrous toluene (10 ml) trimethlphosphine (6.02 mmol) was added and the mixture kept under reflux for 45 min. The resulting cloudy solution was allowed to cool to room temperature and a saturated aqueous solution of NaHCO3 (5 ml) was added. The layers were separated and the aqueous phase was extracted with methylene chloride (4.5 ml). The organic solutions were combined together, dried over anhydrous MgSO₄ and concentrated to dryness, obtaining a white solid. Colorless single crystals suitable for X-ray diffraction analysis were obtained by dissolving the corresponding compound in toluene solution and letting it for slow evaporation at room temperature (Yield: 1.30 g, 92%).