N,N′-Bis(2-methoxy­phen­yl)biphenyl-2,2′-dicarboxamide

Gui-Yu Wang; Di Li; Da-Bin Qin; Jie-Wei Luo; Li-Hui Guo

doi:10.1107/S1600536808032352

. 2008 Oct 11;64(Pt 11):o2104. doi: 10.1107/S1600536808032352

N,N′-Bis(2-methoxyphenyl)biphenyl-2,2′-dicarboxamide

Gui-Yu Wang ^a, Di Li ^a, Da-Bin Qin ^a,^*, Jie-Wei Luo ^a, Li-Hui Guo ^a

PMCID: PMC2959503 PMID: 21580968

Abstract

In the title compound, C₂₈H₂₄N₂O₄, the dihedral angle between the two rings of the biphenyl unit is 75.34 (9)°. The outer aromatic rings form dihedral angles of 66.96 (1) and 85.69 (8)° with the rings to which they are attached . The molecular structure is stabilized by intramolecular C—H⋯O and N—H⋯O hydrogen bonds. In the crystal structure, intermolecular N—H⋯O interactions are observed.

Related literature

For the synthesis, see: Gao & Gao (2002 ▶). For related structures, see: Wang & Han (2004 ▶); Wang & Jiang (2004 ▶); Huang & Yang (2008 ▶).

Experimental

Crystal data

C₂₈H₂₄N₂O₄
M _r = 452.49
Monoclinic,
a = 18.184 (4) Å
b = 16.304 (3) Å
c = 7.9998 (16) Å
β = 108.90 (3)°
V = 2243.9 (8) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 113 (2) K
0.16 × 0.14 × 0.10 mm

Data collection

Rigaku Saturn CCD diffractometer
Absorption correction: multi-scan (CrystalStructure; Rigaku/MSC, 2004 ▶) T _min = 0.986, T _max = 0.991
6422 measured reflections
1991 independent reflections
1858 reflections with I > 2σ(I)
R _int = 0.054

Refinement

R[F ² > 2σ(F ²)] = 0.039
wR(F ²) = 0.093
S = 1.06
1991 reflections
309 parameters
2 restraints
H-atom parameters constrained
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Data collection: RAPID-AUTO (Rigaku/MSC, 2004 ▶); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808032352/gw2044sup1.cif

e-64-o2104-sup1.cif^{(23.5KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808032352/gw2044Isup2.hkl

e-64-o2104-Isup2.hkl^{(98KB, hkl)}

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

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

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O3ⁱ	0.86	2.02	2.833 (3)	157
N2—H2N⋯O2	0.86	2.24	3.081 (4)	167
N2—H2N⋯O4	0.86	2.24	2.612 (3)	106
C22—H22⋯O3	0.93	2.30	2.885 (4)	120

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Symmetry code: (i) Inline graphic .

Acknowledgments

The authors thank the Scientific Research Fund Projects of China West Normal University (grant No. 06B003) and the Youth Fund Projects of Sichuan Education Department (grant No. 2006B039).

supplementary crystallographic information

Comment

The distortion of diphenyl spacer about central bond not only endows dpa a peculiar characterization to link metal ions or metal clusters into macrocycles or helical chains, but also makes diphenic acid (H2dpa) can deprotonate partially forming hydrogen bonds of carboxylic groups to meet both geometric and energetic requirements. We here report the crystal structure of the title compound.

The C8—C13 and C14—C19 planes form the dihedral angle of 75.34 (9)°, and C1—C6 ring are nearly perpendicular to C14—C19 ring, with a dihedral angle of 85.69 (8)°.The molecular structure is stabilized by C—H···O and N—H···O intramolecular hydrogen bonds.In addition, weak C—H···O intermolecular hydrogen bonds are observed.

Experimental

The title compound was prepared according to the reported procedure of M. Z. Gao & Gao (2002). Colourless single crystals suitable for X-ray diffraction were obtained by recrystallization from dimethyl sulfoxide.