organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890

Di­ethyl 4,4′-(diazenediyl)dibenzoate

aDepartment of Chemistry and Environmental Engineering, Anyang Institute of Technology, Henan 455000, People's Republic of China
*Correspondence e-mail: 119yyz@163.com

(Received 22 July 2011; accepted 11 September 2011; online 17 September 2011)

The full mol­ecule of the title compound, C18H18N2O4, is generated by the application of an inversion centre. There are strong ππ inter­actions between adjacent mol­ecules with a centroid–centroid distance of 3.298 (2)Å.

Related literature

For the properties and structures of related compounds, see: Altomare et al. (2005[Altomare, A., Ciardelli, F., Marchini, M. & Solaro, R. (2005). Polymer, 46, 2086-2096.];) Kubo et al. (2005[Kubo, K., Mori, A., Ujiie, S. & Tschierske, C. (2005). J. Oleo Sci. 54, 179-183.]); Harada et al. (1997[Harada, J., Ogawa, K. & Tomoda, S. (1997). Acta Cryst. B53, 662-672.]).

[Scheme 1]

Experimental

Crystal data
  • C18H18N2O4

  • Mr = 326.34

  • Monoclinic, P 21 /c

  • a = 14.844 (3) Å

  • b = 4.5731 (9) Å

  • c = 11.814 (2) Å

  • β = 95.88 (3)°

  • V = 797.7 (3) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.10 mm−1

  • T = 293 K

  • 0.40 × 0.20 × 0.20 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • 13606 measured reflections

  • 1976 independent reflections

  • 1639 reflections with I > 2σ(I)

  • Rint = 0.022

Refinement
  • R[F2 > 2σ(F2)] = 0.050

  • wR(F2) = 0.149

  • S = 1.07

  • 1976 reflections

  • 109 parameters

  • H-atom parameters constrained

  • Δρmax = 0.31 e Å−3

  • Δρmin = −0.25 e Å−3

Data collection: APEX2 (Bruker, 2005[Bruker (2005). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT-Plus (Bruker, 2001[Bruker (2001). SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA]); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information


Comment top

Synthesis, elucidation of crystal structures, and investigation of physical properties of new liquid crystals are important for studying the relationship between molecular stuctures and mesophases. (Kubo et al., 2005). As a contribution to these fields, We report here the synthesis and structure of the title compound.

The title compound (Fig. 1), C18H18N2O4, shows crystallographic inversion symmetry. The intersection angle between two benzene rings is consistent with that of azobenzene (0 °). (Harada et al., 1997) No classic hydrogen bonds are observed in the crystal. There are strong π-π interactions between planar adjacent molecules with the interplanar distance 3.298 Å.

Related literature top

For the properties and structures of related compounds, see: Altomare et al. (2005;) Kubo et al. (2005); Harada et al. (1997).

Experimental top

1.0 g of azobenzene-4,4'-dicarbonylchloride and 20 ml of ethanol were stirred at 353 K for 4 h. After cooling to room temperature a red deposit was obtained. It was then recrystallized from CH2Cl2 to give red crystals suitable for X-ray diffraction analysis.

Refinement top

All H atoms were placed in geometrically idealized positions (C—H = 0.93, 0.96 and 0.97 Å) and treated as riding on their parent atoms with Uiso(H) = 1.2Ueq(C) and 1.5Ueq(C).

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus (Bruker, 2001); 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 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound, with displacement ellipsoids drawn at the 30% probability level. Symmetry code: (i) 2 - x, - y, 2 - z
[Figure 2] Fig. 2. π-π interaction of the molecules.
Diethyl 4,4'-(diazenediyl)dibenzoate top
Crystal data top
C18H18N2O4F(000) = 344
Mr = 326.34Dx = 1.359 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 5335 reflections
a = 14.844 (3) Åθ = 3.5–28.4°
b = 4.5731 (9) ŵ = 0.10 mm1
c = 11.814 (2) ÅT = 293 K
β = 95.88 (3)°Block, red
V = 797.7 (3) Å30.40 × 0.20 × 0.20 mm
Z = 2
Data collection top
Bruker APEXII CCD
diffractometer
1639 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.022
Graphite monochromatorθmax = 28.4°, θmin = 3.5°
ϕ and ω scansh = 1919
13606 measured reflectionsk = 66
1976 independent reflectionsl = 1515
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.050Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.149H-atom parameters constrained
S = 1.07 w = 1/[σ2(Fo2) + (0.0736P)2 + 0.2526P]
where P = (Fo2 + 2Fc2)/3
1976 reflections(Δ/σ)max < 0.001
109 parametersΔρmax = 0.31 e Å3
0 restraintsΔρmin = 0.25 e Å3
Crystal data top
C18H18N2O4V = 797.7 (3) Å3
Mr = 326.34Z = 2
Monoclinic, P21/cMo Kα radiation
a = 14.844 (3) ŵ = 0.10 mm1
b = 4.5731 (9) ÅT = 293 K
c = 11.814 (2) Å0.40 × 0.20 × 0.20 mm
β = 95.88 (3)°
Data collection top
Bruker APEXII CCD
diffractometer
1639 reflections with I > 2σ(I)
13606 measured reflectionsRint = 0.022
1976 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0500 restraints
wR(F2) = 0.149H-atom parameters constrained
S = 1.07Δρmax = 0.31 e Å3
1976 reflectionsΔρmin = 0.25 e Å3
109 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.92686 (8)0.2685 (3)0.93120 (11)0.0327 (3)
C20.86559 (9)0.3422 (3)1.00838 (12)0.0390 (3)
H2A0.86990.25581.08000.047*
C30.92142 (9)0.4028 (3)0.82545 (11)0.0353 (3)
H3A0.96330.35650.77480.042*
C40.85380 (9)0.6061 (3)0.79487 (11)0.0360 (3)
H4A0.85020.69540.72380.043*
C50.79835 (9)0.5450 (3)0.97752 (12)0.0398 (3)
H5A0.75730.59461.02880.048*
C60.79149 (8)0.6754 (3)0.87074 (11)0.0340 (3)
C70.71536 (9)0.8857 (3)0.84138 (13)0.0407 (3)
C80.64597 (12)1.2071 (4)0.69866 (17)0.0604 (5)
H8A0.66961.35270.64980.072*
H8B0.62511.30720.76350.072*
C90.56912 (14)1.0525 (6)0.6352 (2)0.0848 (8)
H9A0.52261.19080.61030.127*
H9B0.54530.90990.68380.127*
H9C0.58960.95650.57020.127*
N10.99820 (7)0.0589 (2)0.95208 (9)0.0354 (3)
O10.65887 (8)0.9411 (3)0.90410 (11)0.0645 (4)
O20.71756 (7)1.0021 (3)0.73787 (10)0.0502 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0323 (6)0.0305 (6)0.0344 (7)0.0026 (5)0.0018 (5)0.0015 (5)
C20.0417 (7)0.0438 (8)0.0315 (7)0.0004 (6)0.0032 (5)0.0052 (5)
C30.0359 (6)0.0373 (7)0.0329 (7)0.0013 (5)0.0039 (5)0.0006 (5)
C40.0392 (6)0.0380 (7)0.0303 (6)0.0012 (5)0.0008 (5)0.0017 (5)
C50.0363 (6)0.0469 (8)0.0368 (7)0.0007 (6)0.0071 (5)0.0010 (6)
C60.0311 (6)0.0337 (6)0.0361 (7)0.0019 (5)0.0016 (5)0.0033 (5)
C70.0344 (6)0.0404 (7)0.0462 (8)0.0016 (5)0.0005 (5)0.0048 (6)
C80.0546 (9)0.0584 (10)0.0651 (11)0.0187 (8)0.0086 (8)0.0054 (9)
C90.0547 (10)0.1064 (19)0.0875 (16)0.0183 (11)0.0209 (10)0.0167 (14)
N10.0370 (6)0.0347 (6)0.0334 (6)0.0007 (4)0.0009 (4)0.0008 (4)
O10.0515 (7)0.0768 (9)0.0673 (8)0.0215 (6)0.0171 (6)0.0054 (7)
O20.0468 (6)0.0546 (7)0.0475 (6)0.0157 (5)0.0033 (5)0.0054 (5)
Geometric parameters (Å, º) top
C1—C31.3870 (18)C6—C71.4972 (18)
C1—C21.3934 (19)C7—O11.2015 (18)
C1—N11.4311 (17)C7—O21.3371 (19)
C2—C51.384 (2)C8—O21.4568 (18)
C2—H2A0.9300C8—C91.479 (3)
C3—C41.3883 (18)C8—H8A0.9700
C3—H3A0.9300C8—H8B0.9700
C4—C61.3890 (19)C9—H9A0.9600
C4—H4A0.9300C9—H9B0.9600
C5—C61.3896 (19)C9—H9C0.9600
C5—H5A0.9300N1—N1i1.250 (2)
C3—C1—C2120.05 (12)O1—C7—O2124.33 (14)
C3—C1—N1115.19 (12)O1—C7—C6123.40 (14)
C2—C1—N1124.76 (12)O2—C7—C6112.27 (12)
C5—C2—C1119.41 (13)O2—C8—C9110.67 (16)
C5—C2—H2A120.3O2—C8—H8A109.5
C1—C2—H2A120.3C9—C8—H8A109.5
C1—C3—C4120.31 (12)O2—C8—H8B109.5
C1—C3—H3A119.8C9—C8—H8B109.5
C4—C3—H3A119.8H8A—C8—H8B108.1
C3—C4—C6119.77 (12)C8—C9—H9A109.5
C3—C4—H4A120.1C8—C9—H9B109.5
C6—C4—H4A120.1H9A—C9—H9B109.5
C2—C5—C6120.71 (13)C8—C9—H9C109.5
C2—C5—H5A119.6H9A—C9—H9C109.5
C6—C5—H5A119.6H9B—C9—H9C109.5
C4—C6—C5119.73 (12)N1i—N1—C1114.02 (14)
C4—C6—C7122.27 (12)C7—O2—C8117.50 (13)
C5—C6—C7117.99 (12)
C3—C1—C2—C51.4 (2)C4—C6—C7—O1177.29 (15)
N1—C1—C2—C5178.86 (12)C5—C6—C7—O12.0 (2)
C2—C1—C3—C41.5 (2)C4—C6—C7—O22.41 (19)
N1—C1—C3—C4178.77 (11)C5—C6—C7—O2178.28 (12)
C1—C3—C4—C60.1 (2)C3—C1—N1—N1i179.91 (13)
C1—C2—C5—C60.0 (2)C2—C1—N1—N1i0.2 (2)
C3—C4—C6—C51.2 (2)O1—C7—O2—C80.7 (2)
C3—C4—C6—C7178.06 (12)C6—C7—O2—C8179.05 (12)
C2—C5—C6—C41.3 (2)C9—C8—O2—C791.4 (2)
C2—C5—C6—C7178.04 (12)
Symmetry code: (i) x+2, y, z+2.

Experimental details

Crystal data
Chemical formulaC18H18N2O4
Mr326.34
Crystal system, space groupMonoclinic, P21/c
Temperature (K)293
a, b, c (Å)14.844 (3), 4.5731 (9), 11.814 (2)
β (°) 95.88 (3)
V3)797.7 (3)
Z2
Radiation typeMo Kα
µ (mm1)0.10
Crystal size (mm)0.40 × 0.20 × 0.20
Data collection
DiffractometerBruker APEXII CCD
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
13606, 1976, 1639
Rint0.022
(sin θ/λ)max1)0.669
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.050, 0.149, 1.07
No. of reflections1976
No. of parameters109
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.31, 0.25

Computer programs: APEX2 (Bruker, 2005), SAINT-Plus (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

 

Acknowledgements

This work was supported by the key subject of applied chemistry of Anyang Institute of Technology.

References

First citationAltomare, A., Ciardelli, F., Marchini, M. & Solaro, R. (2005). Polymer, 46, 2086–2096.  Web of Science CrossRef CAS
First citationBruker (2001). SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA
First citationBruker (2005). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA.
First citationHarada, J., Ogawa, K. & Tomoda, S. (1997). Acta Cryst. B53, 662–672.  CSD CrossRef CAS Web of Science IUCr Journals
First citationKubo, K., Mori, A., Ujiie, S. & Tschierske, C. (2005). J. Oleo Sci. 54, 179–183.  CrossRef CAS
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals

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ISSN: 2056-9890
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