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Acta Crystallogr Sect E Struct Rep Online. 2008 November 1; 64(Pt 11): o2104.
Published online 2008 October 11. doi:  10.1107/S1600536808032352
PMCID: PMC2959503

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

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 [triangle]). For related structures, see: Wang & Han (2004 [triangle]); Wang & Jiang (2004 [triangle]); Huang & Yang (2008 [triangle]).

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Object name is e-64-o2104-scheme1.jpg

Experimental

Crystal data

  • C28H24N2O4
  • M r = 452.49
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-o2104-efi1.jpg
  • 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 [triangle]) 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
  • Δρmax = 0.17 e Å−3
  • Δρmin = −0.20 e Å−3

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

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

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

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

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

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.

Refinement

H atoms were placed in calculated positions with C—H = 0.93 Å, and N—H = 0.86 Å,and refined in riding mode with Uiso(H) = 1.2Ueq(C,N).

Figures

Fig. 1.
The molecular structure of the title compound, showing 30% probability displacement ellipsoids and the atomic numbering.

Crystal data

C28H24N2O4F(000) = 952
Mr = 452.49Dx = 1.339 Mg m3
Monoclinic, CcMo Kα radiation, λ = 0.71073 Å
a = 18.184 (4) ÅCell parameters from 3190 reflections
b = 16.304 (3) Åθ = 1.7–27.9°
c = 7.9998 (16) ŵ = 0.09 mm1
β = 108.90 (3)°T = 113 K
V = 2243.9 (8) Å3Block, colourless
Z = 40.16 × 0.14 × 0.10 mm

Data collection

Rigaku Saturn diffractometer1991 independent reflections
Radiation source: rotating anode1858 reflections with I > 2σ(I)
confocalRint = 0.054
ω scansθmax = 25.0°, θmin = 1.7°
Absorption correction: multi-scan (CrystalStructure; Rigaku/MSC, 2004)h = −21→20
Tmin = 0.986, Tmax = 0.991k = −17→19
6422 measured reflectionsl = −9→9

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.039Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.093H-atom parameters constrained
S = 1.06w = 1/[σ2(Fo2) + (0.0537P)2] where P = (Fo2 + 2Fc2)/3
1991 reflections(Δ/σ)max = 0.007
309 parametersΔρmax = 0.17 e Å3
2 restraintsΔρmin = −0.20 e Å3

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
O1−0.01240 (15)0.26417 (14)0.9137 (3)0.0338 (6)
O20.21854 (13)0.17729 (12)1.0081 (2)0.0234 (5)
O30.45976 (12)0.32159 (13)1.0239 (2)0.0239 (5)
O40.31213 (13)0.07137 (13)0.8380 (3)0.0273 (5)
N10.09211 (15)0.17216 (15)0.8317 (3)0.0222 (6)
H1N0.06150.18010.72580.027*
N20.37809 (15)0.21050 (14)0.9645 (3)0.0216 (6)
H2N0.33500.19320.97430.026*
C10.00360 (19)0.19053 (18)0.9988 (4)0.0229 (7)
C2−0.0328 (2)0.16090 (19)1.1154 (4)0.0277 (7)
H2−0.06940.19281.14410.033*
C3−0.0139 (2)0.0831 (2)1.1889 (4)0.0298 (8)
H3−0.03780.06321.26740.036*
C40.0399 (2)0.0355 (2)1.1457 (4)0.0305 (8)
H40.0512−0.01701.19260.037*
C50.07701 (19)0.06580 (18)1.0327 (3)0.0258 (7)
H50.11480.03451.00720.031*
C60.05817 (18)0.14248 (18)0.9576 (3)0.0210 (7)
C70.16777 (18)0.18877 (17)0.8643 (3)0.0188 (6)
C80.18756 (18)0.22120 (18)0.7085 (3)0.0201 (7)
C90.16253 (18)0.17982 (18)0.5469 (4)0.0219 (7)
H90.13040.13420.53360.026*
C100.18522 (19)0.20637 (19)0.4066 (3)0.0251 (7)
H100.16950.17790.30000.030*
C110.2317 (2)0.27591 (19)0.4260 (4)0.0275 (7)
H110.24710.29400.33210.033*
C120.25501 (19)0.31821 (19)0.5843 (4)0.0252 (7)
H120.28530.36510.59560.030*
C130.23333 (17)0.29096 (18)0.7281 (3)0.0190 (6)
C140.25474 (18)0.34128 (17)0.8950 (3)0.0204 (6)
C150.1978 (2)0.39160 (18)0.9223 (4)0.0270 (7)
H150.14750.39010.84280.032*
C160.2152 (2)0.4441 (2)1.0670 (4)0.0307 (8)
H160.17630.47661.08470.037*
C170.2897 (2)0.44812 (19)1.1841 (4)0.0290 (8)
H170.30150.48371.28000.035*
C180.34668 (19)0.39879 (18)1.1576 (4)0.0244 (7)
H180.39720.40211.23550.029*
C190.32979 (19)0.34399 (18)1.0156 (3)0.0211 (6)
C200.39544 (18)0.29130 (17)1.0011 (3)0.0210 (7)
C210.42452 (18)0.15199 (18)0.9115 (3)0.0212 (7)
C220.5013 (2)0.1627 (2)0.9232 (4)0.0317 (8)
H220.52760.20990.97560.038*
C230.5398 (2)0.1035 (2)0.8573 (5)0.0407 (9)
H230.59180.11110.86740.049*
C240.5015 (2)0.0338 (2)0.7773 (4)0.0354 (8)
H240.5271−0.00480.73050.042*
C250.4250 (2)0.0217 (2)0.7669 (4)0.0275 (8)
H250.3988−0.02520.71270.033*
C260.38714 (18)0.07931 (18)0.8372 (3)0.0225 (7)
C280.2734 (2)−0.0051 (2)0.7829 (5)0.0366 (9)
H28A0.2719−0.01680.66420.055*
H28B0.2214−0.00190.78730.055*
H28C0.3011−0.04800.86010.055*
C27−0.0779 (3)0.3085 (2)0.9290 (5)0.0458 (10)
H27A−0.12340.27460.88920.069*
H27B−0.08560.35710.85780.069*
H27C−0.06840.32341.05020.069*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.0436 (16)0.0284 (13)0.0359 (11)0.0087 (11)0.0218 (11)0.0078 (9)
O20.0200 (12)0.0303 (12)0.0181 (10)−0.0008 (9)0.0038 (9)0.0020 (8)
O30.0182 (13)0.0273 (12)0.0252 (10)−0.0060 (9)0.0054 (10)−0.0002 (8)
O40.0194 (12)0.0223 (12)0.0408 (11)−0.0041 (9)0.0104 (10)−0.0049 (9)
N10.0164 (14)0.0333 (15)0.0163 (11)−0.0017 (11)0.0045 (11)0.0036 (9)
N20.0172 (14)0.0205 (14)0.0279 (13)0.0000 (10)0.0084 (11)−0.0017 (10)
C10.0267 (18)0.0191 (15)0.0228 (14)−0.0017 (13)0.0076 (13)0.0001 (11)
C20.030 (2)0.0306 (19)0.0255 (14)0.0003 (14)0.0135 (15)−0.0028 (12)
C30.039 (2)0.0303 (19)0.0251 (14)−0.0089 (15)0.0176 (16)0.0009 (12)
C40.042 (2)0.0234 (18)0.0272 (16)0.0002 (14)0.0133 (16)0.0033 (12)
C50.030 (2)0.0248 (17)0.0225 (14)0.0023 (14)0.0082 (14)−0.0017 (12)
C60.0203 (17)0.0250 (17)0.0163 (12)−0.0035 (12)0.0042 (13)−0.0008 (11)
C70.0183 (17)0.0183 (15)0.0201 (14)0.0011 (12)0.0066 (14)−0.0023 (11)
C80.0134 (16)0.0294 (18)0.0170 (12)0.0040 (12)0.0045 (12)0.0016 (11)
C90.0174 (17)0.0245 (17)0.0219 (14)−0.0004 (13)0.0036 (13)−0.0011 (11)
C100.0213 (19)0.0347 (18)0.0182 (13)0.0025 (14)0.0050 (13)−0.0018 (11)
C110.028 (2)0.0348 (19)0.0219 (14)0.0019 (14)0.0117 (14)0.0081 (12)
C120.0236 (19)0.0249 (17)0.0278 (15)−0.0002 (13)0.0094 (14)0.0035 (12)
C130.0123 (16)0.0232 (16)0.0209 (13)0.0025 (11)0.0045 (12)0.0027 (11)
C140.0205 (17)0.0175 (15)0.0238 (14)−0.0011 (12)0.0079 (13)0.0020 (11)
C150.0231 (18)0.0254 (17)0.0305 (15)0.0006 (14)0.0057 (14)0.0010 (12)
C160.032 (2)0.0278 (19)0.0365 (17)0.0041 (14)0.0167 (17)−0.0022 (13)
C170.037 (2)0.0222 (17)0.0277 (15)−0.0017 (14)0.0105 (15)−0.0026 (12)
C180.0267 (19)0.0206 (17)0.0239 (14)−0.0020 (13)0.0054 (13)−0.0010 (11)
C190.0221 (17)0.0192 (16)0.0234 (14)0.0007 (12)0.0091 (14)0.0030 (11)
C200.0223 (19)0.0250 (17)0.0143 (13)−0.0018 (13)0.0041 (13)0.0012 (10)
C210.0207 (18)0.0212 (16)0.0222 (14)0.0009 (12)0.0076 (14)−0.0005 (11)
C220.0246 (19)0.0289 (18)0.0423 (17)−0.0024 (14)0.0118 (16)−0.0068 (14)
C230.0207 (19)0.042 (2)0.063 (2)−0.0016 (15)0.0182 (18)−0.0110 (17)
C240.034 (2)0.029 (2)0.0465 (19)0.0069 (15)0.0177 (17)−0.0012 (14)
C250.031 (2)0.0201 (17)0.0321 (16)−0.0004 (13)0.0110 (15)−0.0015 (12)
C260.0204 (19)0.0219 (16)0.0241 (14)−0.0011 (12)0.0059 (13)0.0019 (11)
C280.033 (2)0.031 (2)0.0477 (19)−0.0132 (15)0.0152 (17)−0.0088 (14)
C270.062 (3)0.037 (2)0.049 (2)0.0233 (19)0.032 (2)0.0113 (16)

Geometric parameters (Å, °)

O1—C11.364 (4)C12—C131.403 (4)
O1—C271.431 (4)C12—H120.9300
O2—C71.234 (3)C13—C141.507 (4)
O3—C201.228 (4)C14—C191.394 (4)
O4—C261.372 (4)C14—C151.393 (4)
O4—C281.429 (4)C15—C161.390 (4)
N1—C71.342 (4)C15—H150.9300
N1—C61.425 (4)C16—C171.377 (5)
N1—H1N0.8600C16—H160.9300
N2—C201.364 (4)C17—C181.381 (5)
N2—C211.426 (4)C17—H170.9300
N2—H2N0.8600C18—C191.398 (4)
C1—C61.385 (5)C18—H180.9300
C1—C21.393 (4)C19—C201.506 (4)
C2—C31.393 (5)C21—C221.380 (5)
C2—H20.9300C21—C261.399 (4)
C3—C41.377 (5)C22—C231.393 (5)
C3—H30.9300C22—H220.9300
C4—C51.383 (5)C23—C241.377 (5)
C4—H40.9300C23—H230.9300
C5—C61.381 (4)C24—C251.381 (5)
C5—H50.9300C24—H240.9300
C7—C81.501 (4)C25—C261.387 (4)
C8—C131.388 (4)C25—H250.9300
C8—C91.397 (4)C28—H28A0.9600
C9—C101.385 (4)C28—H28B0.9600
C9—H90.9300C28—H28C0.9600
C10—C111.392 (5)C27—H27A0.9600
C10—H100.9300C27—H27B0.9600
C11—C121.383 (4)C27—H27C0.9600
C11—H110.9300
C1—O1—C27116.8 (3)C15—C14—C13117.9 (3)
C26—O4—C28118.1 (2)C16—C15—C14120.8 (3)
C7—N1—C6125.6 (2)C16—C15—H15119.6
C7—N1—H1N117.2C14—C15—H15119.6
C6—N1—H1N117.2C17—C16—C15120.3 (3)
C20—N2—C21126.3 (3)C17—C16—H16119.9
C20—N2—H2N116.9C15—C16—H16119.9
C21—N2—H2N116.9C16—C17—C18119.3 (3)
O1—C1—C6115.6 (3)C16—C17—H17120.3
O1—C1—C2124.6 (3)C18—C17—H17120.3
C6—C1—C2119.7 (3)C17—C18—C19121.2 (3)
C1—C2—C3119.5 (3)C17—C18—H18119.4
C1—C2—H2120.2C19—C18—H18119.4
C3—C2—H2120.2C14—C19—C18119.4 (3)
C4—C3—C2120.3 (3)C14—C19—C20123.5 (3)
C4—C3—H3119.8C18—C19—C20117.1 (3)
C2—C3—H3119.8O3—C20—N2124.3 (3)
C3—C4—C5120.0 (3)O3—C20—C19120.0 (3)
C3—C4—H4120.0N2—C20—C19115.7 (3)
C5—C4—H4120.0C22—C21—C26118.6 (3)
C6—C5—C4120.2 (3)C22—C21—N2125.3 (3)
C6—C5—H5119.9C26—C21—N2116.1 (3)
C4—C5—H5119.9C21—C22—C23120.5 (3)
C5—C6—C1120.3 (3)C21—C22—H22119.7
C5—C6—N1120.8 (3)C23—C22—H22119.7
C1—C6—N1118.9 (3)C24—C23—C22120.5 (3)
O2—C7—N1124.1 (3)C24—C23—H23119.7
O2—C7—C8121.3 (3)C22—C23—H23119.7
N1—C7—C8114.6 (2)C23—C24—C25119.6 (3)
C13—C8—C9120.3 (3)C23—C24—H24120.2
C13—C8—C7119.4 (2)C25—C24—H24120.2
C9—C8—C7120.3 (3)C24—C25—C26120.1 (3)
C10—C9—C8120.4 (3)C24—C25—H25120.0
C10—C9—H9119.8C26—C25—H25120.0
C8—C9—H9119.8O4—C26—C25124.3 (3)
C9—C10—C11119.6 (3)O4—C26—C21115.1 (3)
C9—C10—H10120.2C25—C26—C21120.6 (3)
C11—C10—H10120.2O4—C28—H28A109.5
C12—C11—C10120.2 (3)O4—C28—H28B109.5
C12—C11—H11119.9H28A—C28—H28B109.5
C10—C11—H11119.9O4—C28—H28C109.5
C11—C12—C13120.6 (3)H28A—C28—H28C109.5
C11—C12—H12119.7H28B—C28—H28C109.5
C13—C12—H12119.7O1—C27—H27A109.5
C8—C13—C12119.0 (3)O1—C27—H27B109.5
C8—C13—C14121.3 (2)H27A—C27—H27B109.5
C12—C13—C14119.6 (3)O1—C27—H27C109.5
C19—C14—C15118.9 (3)H27A—C27—H27C109.5
C19—C14—C13123.0 (3)H27B—C27—H27C109.5
C27—O1—C1—C6169.2 (3)C8—C13—C14—C15−75.3 (4)
C27—O1—C1—C2−8.3 (4)C12—C13—C14—C1599.9 (3)
O1—C1—C2—C3177.3 (3)C19—C14—C15—C160.3 (4)
C6—C1—C2—C3−0.2 (4)C13—C14—C15—C16−175.3 (3)
C1—C2—C3—C4−0.4 (5)C14—C15—C16—C171.2 (5)
C2—C3—C4—C51.8 (5)C15—C16—C17—C18−0.8 (5)
C3—C4—C5—C6−2.5 (4)C16—C17—C18—C19−1.0 (5)
C4—C5—C6—C11.8 (4)C15—C14—C19—C18−2.0 (4)
C4—C5—C6—N1−175.7 (3)C13—C14—C19—C18173.3 (3)
O1—C1—C6—C5−178.2 (3)C15—C14—C19—C20178.8 (3)
C2—C1—C6—C5−0.5 (4)C13—C14—C19—C20−5.9 (4)
O1—C1—C6—N1−0.6 (4)C17—C18—C19—C142.4 (4)
C2—C1—C6—N1177.1 (3)C17—C18—C19—C20−178.4 (3)
C7—N1—C6—C5−65.1 (4)C21—N2—C20—O3−13.6 (4)
C7—N1—C6—C1117.3 (3)C21—N2—C20—C19167.3 (2)
C6—N1—C7—O22.9 (5)C14—C19—C20—O3135.1 (3)
C6—N1—C7—C8−178.7 (3)C18—C19—C20—O3−44.0 (4)
O2—C7—C8—C13−50.2 (4)C14—C19—C20—N2−45.7 (4)
N1—C7—C8—C13131.3 (3)C18—C19—C20—N2135.1 (3)
O2—C7—C8—C9127.4 (3)C20—N2—C21—C2214.1 (4)
N1—C7—C8—C9−51.1 (4)C20—N2—C21—C26−163.9 (2)
C13—C8—C9—C102.1 (5)C26—C21—C22—C232.0 (5)
C7—C8—C9—C10−175.5 (3)N2—C21—C22—C23−175.9 (3)
C8—C9—C10—C11−1.6 (5)C21—C22—C23—C240.9 (5)
C9—C10—C11—C120.0 (5)C22—C23—C24—C25−1.8 (6)
C10—C11—C12—C131.1 (5)C23—C24—C25—C26−0.2 (5)
C9—C8—C13—C12−1.1 (4)C28—O4—C26—C258.0 (4)
C7—C8—C13—C12176.6 (3)C28—O4—C26—C21−173.0 (3)
C9—C8—C13—C14174.1 (3)C24—C25—C26—O4−177.9 (3)
C7—C8—C13—C14−8.2 (4)C24—C25—C26—C213.1 (4)
C11—C12—C13—C8−0.5 (5)C22—C21—C26—O4176.9 (3)
C11—C12—C13—C14−175.8 (3)N2—C21—C26—O4−4.9 (3)
C8—C13—C14—C19109.4 (3)C22—C21—C26—C25−4.0 (4)
C12—C13—C14—C19−75.4 (4)N2—C21—C26—C25174.2 (2)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N1—H1N···O3i0.862.022.833 (3)157
N2—H2N···O20.862.243.081 (4)167
N2—H2N···O40.862.242.612 (3)106
C22—H22···O30.932.302.885 (4)120

Symmetry codes: (i) x−1/2, −y+1/2, z−1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: GW2044).

References

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  • Wang, R. H. & Han, L. (2004). J. Mol. Struct.694, 79–83.
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