Diethyl 4,4′-(diazenediyl)dibenzoate

Niu, Y.; Huang, J.; Zhao, C.; Gao, P.; Yu, Y.

doi:10.1107/S1600536811036877

organic compounds

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ISSN: 2056-9890

Volume 67| Part 10| October 2011| Page o2671

https://doi.org/10.1107/S1600536811036877

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Diethyl 4,4′-(diazenediyl)dibenzoate

Yongsheng Niu,^a Jianping Huang,^a Chunpu Zhao,^a Pan Gao ^a and Youzhu Yu ^a ^*

^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 π–π 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 ;) Kubo et al. (2005 ); Harada et al. (1997 ).

Experimental

Crystal data

C₁₈H₁₈N₂O₄
M_r = 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)
R_int = 0.022

Refinement

R[F² > 2σ(F²)] = 0.050
wR(F²) = 0.149
S = 1.07
1976 reflections
109 parameters
H-atom parameters constrained
Δρ_max = 0.31 e Å⁻³
Δρ_min = −0.25 e Å⁻³

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

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536811036877/aa2020sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811036877/aa2020Isup2.hkl

checkCIF report

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.

Structure description top

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

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

	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
	Fig. 2. π-π interaction of the molecules.

Diethyl 4,4'-(diazenediyl)dibenzoate top

Crystal data top

C₁₈H₁₈N₂O₄	F(000) = 344
M_r = 326.34	D_x = 1.359 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5335 reflections
a = 14.844 (3) Å	θ = 3.5–28.4°
b = 4.5731 (9) Å	µ = 0.10 mm⁻¹
c = 11.814 (2) Å	T = 293 K
β = 95.88 (3)°	Block, red
V = 797.7 (3) Å³	0.40 × 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 tube	R_int = 0.022
Graphite monochromator	θ_max = 28.4°, θ_min = 3.5°
φ and ω scans	h = −19→19
13606 measured reflections	k = −6→6
1976 independent reflections	l = −15→15

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.149	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.0736P)² + 0.2526P] where P = (F_o² + 2F_c²)/3
1976 reflections	(Δ/σ)_max < 0.001
109 parameters	Δρ_max = 0.31 e Å⁻³
0 restraints	Δρ_min = −0.25 e Å⁻³

Crystal data top

C₁₈H₁₈N₂O₄	V = 797.7 (3) Å³
M_r = 326.34	Z = 2
Monoclinic, P2₁/c	Mo Kα radiation
a = 14.844 (3) Å	µ = 0.10 mm⁻¹
b = 4.5731 (9) Å	T = 293 K
c = 11.814 (2) Å	0.40 × 0.20 × 0.20 mm
β = 95.88 (3)°

Data collection top

Bruker APEXII CCD diffractometer	1639 reflections with I > 2σ(I)
13606 measured reflections	R_int = 0.022
1976 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.050	0 restraints
wR(F²) = 0.149	H-atom parameters constrained
S = 1.07	Δρ_max = 0.31 e Å⁻³
1976 reflections	Δρ_min = −0.25 e Å⁻³
109 parameters

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

	x	y	z	U_iso*/U_eq
C1	0.92686 (8)	0.2685 (3)	0.93120 (11)	0.0327 (3)
C2	0.86559 (9)	0.3422 (3)	1.00838 (12)	0.0390 (3)
H2A	0.8699	0.2558	1.0800	0.047*
C3	0.92142 (9)	0.4028 (3)	0.82545 (11)	0.0353 (3)
H3A	0.9633	0.3565	0.7748	0.042*
C4	0.85380 (9)	0.6061 (3)	0.79487 (11)	0.0360 (3)
H4A	0.8502	0.6954	0.7238	0.043*
C5	0.79835 (9)	0.5450 (3)	0.97752 (12)	0.0398 (3)
H5A	0.7573	0.5946	1.0288	0.048*
C6	0.79149 (8)	0.6754 (3)	0.87074 (11)	0.0340 (3)
C7	0.71536 (9)	0.8857 (3)	0.84138 (13)	0.0407 (3)
C8	0.64597 (12)	1.2071 (4)	0.69866 (17)	0.0604 (5)
H8A	0.6696	1.3527	0.6498	0.072*
H8B	0.6251	1.3072	0.7635	0.072*
C9	0.56912 (14)	1.0525 (6)	0.6352 (2)	0.0848 (8)
H9A	0.5226	1.1908	0.6103	0.127*
H9B	0.5453	0.9099	0.6838	0.127*
H9C	0.5896	0.9565	0.5702	0.127*
N1	0.99820 (7)	0.0589 (2)	0.95208 (9)	0.0354 (3)
O1	0.65887 (8)	0.9411 (3)	0.90410 (11)	0.0645 (4)
O2	0.71756 (7)	1.0021 (3)	0.73787 (10)	0.0502 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0323 (6)	0.0305 (6)	0.0344 (7)	−0.0026 (5)	−0.0018 (5)	−0.0015 (5)
C2	0.0417 (7)	0.0438 (8)	0.0315 (7)	−0.0004 (6)	0.0032 (5)	0.0052 (5)
C3	0.0359 (6)	0.0373 (7)	0.0329 (7)	0.0013 (5)	0.0039 (5)	−0.0006 (5)
C4	0.0392 (6)	0.0380 (7)	0.0303 (6)	0.0012 (5)	0.0008 (5)	0.0017 (5)
C5	0.0363 (6)	0.0469 (8)	0.0368 (7)	0.0007 (6)	0.0071 (5)	−0.0010 (6)
C6	0.0311 (6)	0.0337 (6)	0.0361 (7)	−0.0019 (5)	−0.0016 (5)	−0.0033 (5)
C7	0.0344 (6)	0.0404 (7)	0.0462 (8)	0.0016 (5)	−0.0005 (5)	−0.0048 (6)
C8	0.0546 (9)	0.0584 (10)	0.0651 (11)	0.0187 (8)	−0.0086 (8)	0.0054 (9)
C9	0.0547 (10)	0.1064 (19)	0.0875 (16)	0.0183 (11)	−0.0209 (10)	−0.0167 (14)
N1	0.0370 (6)	0.0347 (6)	0.0334 (6)	−0.0007 (4)	−0.0009 (4)	0.0008 (4)
O1	0.0515 (7)	0.0768 (9)	0.0673 (8)	0.0215 (6)	0.0171 (6)	0.0054 (7)
O2	0.0468 (6)	0.0546 (7)	0.0475 (6)	0.0157 (5)	−0.0033 (5)	0.0054 (5)

Geometric parameters (Å, º) top

C1—C3	1.3870 (18)	C6—C7	1.4972 (18)
C1—C2	1.3934 (19)	C7—O1	1.2015 (18)
C1—N1	1.4311 (17)	C7—O2	1.3371 (19)
C2—C5	1.384 (2)	C8—O2	1.4568 (18)
C2—H2A	0.9300	C8—C9	1.479 (3)
C3—C4	1.3883 (18)	C8—H8A	0.9700
C3—H3A	0.9300	C8—H8B	0.9700
C4—C6	1.3890 (19)	C9—H9A	0.9600
C4—H4A	0.9300	C9—H9B	0.9600
C5—C6	1.3896 (19)	C9—H9C	0.9600
C5—H5A	0.9300	N1—N1ⁱ	1.250 (2)

C3—C1—C2	120.05 (12)	O1—C7—O2	124.33 (14)
C3—C1—N1	115.19 (12)	O1—C7—C6	123.40 (14)
C2—C1—N1	124.76 (12)	O2—C7—C6	112.27 (12)
C5—C2—C1	119.41 (13)	O2—C8—C9	110.67 (16)
C5—C2—H2A	120.3	O2—C8—H8A	109.5
C1—C2—H2A	120.3	C9—C8—H8A	109.5
C1—C3—C4	120.31 (12)	O2—C8—H8B	109.5
C1—C3—H3A	119.8	C9—C8—H8B	109.5
C4—C3—H3A	119.8	H8A—C8—H8B	108.1
C3—C4—C6	119.77 (12)	C8—C9—H9A	109.5
C3—C4—H4A	120.1	C8—C9—H9B	109.5
C6—C4—H4A	120.1	H9A—C9—H9B	109.5
C2—C5—C6	120.71 (13)	C8—C9—H9C	109.5
C2—C5—H5A	119.6	H9A—C9—H9C	109.5
C6—C5—H5A	119.6	H9B—C9—H9C	109.5
C4—C6—C5	119.73 (12)	N1ⁱ—N1—C1	114.02 (14)
C4—C6—C7	122.27 (12)	C7—O2—C8	117.50 (13)
C5—C6—C7	117.99 (12)

C3—C1—C2—C5	1.4 (2)	C4—C6—C7—O1	177.29 (15)
N1—C1—C2—C5	−178.86 (12)	C5—C6—C7—O1	−2.0 (2)
C2—C1—C3—C4	−1.5 (2)	C4—C6—C7—O2	−2.41 (19)
N1—C1—C3—C4	178.77 (11)	C5—C6—C7—O2	178.28 (12)
C1—C3—C4—C6	0.1 (2)	C3—C1—N1—N1ⁱ	179.91 (13)
C1—C2—C5—C6	0.0 (2)	C2—C1—N1—N1ⁱ	0.2 (2)
C3—C4—C6—C5	1.2 (2)	O1—C7—O2—C8	−0.7 (2)
C3—C4—C6—C7	−178.06 (12)	C6—C7—O2—C8	179.05 (12)
C2—C5—C6—C4	−1.3 (2)	C9—C8—O2—C7	−91.4 (2)
C2—C5—C6—C7	178.04 (12)

Symmetry code: (i) −x+2, −y, −z+2.

Experimental details

Crystal data
Chemical formula	C₁₈H₁₈N₂O₄
M_r	326.34
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	14.844 (3), 4.5731 (9), 11.814 (2)
β (°)	95.88 (3)
V (Å³)	797.7 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.40 × 0.20 × 0.20

Data collection
Diffractometer	Bruker APEXII CCD
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	13606, 1976, 1639
R_int	0.022
(sin θ/λ)_max (Å⁻¹)	0.669

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.050, 0.149, 1.07
No. of reflections	1976
No. of parameters	109
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	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

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