Diethyl 4,4'-(diazenediyl)dibenzoate.

The full mol-ecule of the title compound, C(18)H(18)N(2)O(4), is generated by the application of an inversion centre. There are strong π-π inter-actions between adjacent mol-ecules 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 = 326.34

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 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 ▶); 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.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811036877/aa2020sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811036877/aa2020Isup2.hkl

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

C18H18N2O4	F(000) = 344
Mr = 326.34	Dx = 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

Bruker APEXII CCD diffractometer	1639 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.022
graphite	θmax = 28.4°, θmin = 3.5°
φ and ω scans	h = −19→19
13606 measured reflections	k = −6→6
1976 independent reflections	l = −15→15

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(Fo2) + (0.0736P)2 + 0.2526P] where P = (Fo2 + 2Fc2)/3
1976 reflections	(Δ/σ)max < 0.001
109 parameters	Δρmax = 0.31 e Å−3
0 restraints	Δρmin = −0.25 e Å−3

	x	y	z	Uiso*/Ueq
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)

	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)

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)