Dimethyl 4,4'-(diazenedi-yl)dibenzoate at 100 K.

In the asymmetric part of the unit cell of the title compound, C16H14N2O4, there are two chemically equivalent but crystallographic independent half mol-ecules. The geometric centre of each complete mol-ecule lies on a crystallographic inversion centre. Both mol-ecules are almost planar [mean deviations of atoms in the two molecules are 0.032 (2) and 0.044 (2) Å] and their geometries are similar. In the crystal, mol-ecules are arranged in columns along the a axis. There are no inter-molecular donor-acceptor distances shorter than 3.4 Å.

Related literature

For general background to the use of azo compounds as dyes, pigments and advanced materials, see: Allmann (1997 ▶); Scott et al., (2002 ▶); Maniam et al. (2008 ▶); Zeitouny et al., (2009 ▶). For a related structure, see: Yu & Liu (2009 ▶); Niu et al. (2011 ▶). For related literature, see: Onto et al. (1998 ▶). For the Cambridge Structural Database, see: Allen (2002 ▶).

Experimental

Crystal data

C16H14N2O4

M = 298.29

Triclinic,

a = 3.8146 (8) Å

b = 11.2571 (18) Å

c = 16.904 (3) Å

α = 72.456 (16)°

β = 85.030 (18)°

γ = 84.468 (16)°

V = 687.6 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.11 mm−1

T = 100 K

0.35 × 0.17 × 0.15 mm

Data collection

Oxford Diffraction Xcalibur diffractometer

4264 measured reflections

2405 independent reflections

1652 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.147

S = 1.05

2405 reflections

213 parameters

H-atom parameters constrained

Δρmax = 0.32 e Å−3

Δρmin = −0.25 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2008 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2008 ▶); data reduction: CrysAlis RED; 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: SHELXL97.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813026846/fk2074sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813026846/fk2074Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813026846/fk2074Isup3.cml

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

C16H14N2O4	Z = 2
Mr = 298.29	F(000) = 312
Triclinic, P1	Dx = 1.441 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 3.8146 (8) Å	Cell parameters from 4264 reflections
b = 11.2571 (18) Å	θ = 3.6–25.0°
c = 16.904 (3) Å	µ = 0.11 mm−1
α = 72.456 (16)°	T = 100 K
β = 85.030 (18)°	Prism, red
γ = 84.468 (16)°	0.35 × 0.17 × 0.15 mm
V = 687.6 (2) Å3

Oxford Diffraction Xcalibur diffractometer	1652 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.025
Graphite monochromator	θmax = 25.0°, θmin = 3.6°
Detector resolution: 1024 x 1024 with blocks 2 x 2 pixels mm-1	h = −4→2
ω–scan	k = −13→13
4264 measured reflections	l = −20→20
2405 independent reflections

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.147	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0791P)2 + 0.205P] where P = (Fo2 + 2Fc2)/3
2405 reflections	(Δ/σ)max < 0.001
213 parameters	Δρmax = 0.32 e Å−3
0 restraints	Δρmin = −0.25 e Å−3

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.

	x	y	z	Uiso*/Ueq
O11	0.3301 (4)	0.15744 (14)	0.33935 (9)	0.0251 (4)
O12	0.1772 (4)	−0.04021 (15)	0.39802 (10)	0.0296 (4)
N11	0.0393 (5)	0.05005 (17)	0.00495 (12)	0.0216 (5)
C11	0.0777 (6)	0.0436 (2)	0.08962 (14)	0.0191 (5)
C12	0.2050 (6)	0.1480 (2)	0.10194 (14)	0.0196 (5)
H12	0.2585	0.2160	0.0565	0.020 (6)*
C13	0.2522 (5)	0.1511 (2)	0.18173 (14)	0.0191 (5)
H13	0.3387	0.2208	0.1898	0.025 (6)*
C14	0.1695 (5)	0.0493 (2)	0.25002 (14)	0.0194 (5)
C15	0.0372 (6)	−0.0548 (2)	0.23750 (14)	0.0204 (5)
H15	−0.0194	−0.1222	0.2830	0.020 (6)*
C16	−0.0101 (6)	−0.0585 (2)	0.15834 (14)	0.0200 (5)
H16	−0.0992	−0.1278	0.1504	0.028 (7)*
C17	0.2225 (6)	0.0484 (2)	0.33681 (14)	0.0209 (5)
C18	0.3974 (7)	0.1652 (2)	0.42107 (14)	0.0272 (6)
H18A	0.4725	0.2464	0.4158	0.037 (7)*
H18B	0.5788	0.1025	0.4448	0.031 (7)*
H18C	0.1852	0.1519	0.4565	0.038 (8)*
O21	0.6465 (4)	0.65469 (14)	0.35059 (10)	0.0248 (4)
O22	0.8894 (4)	0.45639 (15)	0.38736 (10)	0.0308 (5)
N21	0.4726 (5)	0.55083 (17)	0.00854 (12)	0.0206 (4)
C21	0.5457 (6)	0.5432 (2)	0.09183 (14)	0.0184 (5)
C22	0.4325 (6)	0.6478 (2)	0.11755 (14)	0.0193 (5)
H22	0.3167	0.7168	0.0815	0.034 (7)*
C23	0.4932 (5)	0.6485 (2)	0.19724 (13)	0.0188 (5)
H23	0.4175	0.7183	0.2145	0.027 (7)*
C24	0.6678 (6)	0.5450 (2)	0.25183 (14)	0.0194 (5)
C25	0.7813 (5)	0.4400 (2)	0.22548 (14)	0.0196 (5)
H25	0.8971	0.3710	0.2616	0.023 (6)*
C26	0.7222 (6)	0.4383 (2)	0.14616 (14)	0.0193 (5)
H26	0.7983	0.3686	0.1288	0.027 (7)*
C27	0.7478 (6)	0.5448 (2)	0.33667 (14)	0.0212 (5)
C28	0.7220 (7)	0.6663 (2)	0.43076 (14)	0.0279 (6)
H28A	0.6386	0.7481	0.4340	0.046 (8)*
H28B	0.9720	0.6542	0.4368	0.031 (7)*
H28C	0.6053	0.6044	0.4744	0.039 (8)*

	U11	U22	U33	U12	U13	U23
O11	0.0366 (10)	0.0189 (9)	0.0242 (9)	−0.0057 (7)	−0.0049 (7)	−0.0110 (7)
O12	0.0411 (11)	0.0227 (10)	0.0250 (9)	−0.0081 (8)	−0.0030 (8)	−0.0052 (7)
N11	0.0227 (10)	0.0171 (10)	0.0270 (11)	−0.0007 (8)	−0.0018 (8)	−0.0096 (8)
C11	0.0183 (11)	0.0165 (12)	0.0233 (12)	0.0047 (9)	−0.0021 (9)	−0.0089 (9)
C12	0.0205 (11)	0.0136 (12)	0.0239 (13)	−0.0017 (9)	−0.0001 (9)	−0.0047 (9)
C13	0.0184 (11)	0.0133 (11)	0.0289 (13)	−0.0003 (9)	−0.0020 (9)	−0.0114 (10)
C14	0.0163 (11)	0.0185 (12)	0.0253 (13)	0.0014 (9)	−0.0019 (9)	−0.0100 (10)
C15	0.0232 (12)	0.0140 (11)	0.0228 (12)	−0.0005 (9)	−0.0017 (10)	−0.0039 (9)
C16	0.0198 (11)	0.0150 (12)	0.0274 (13)	−0.0027 (9)	−0.0005 (10)	−0.0094 (10)
C17	0.0203 (12)	0.0174 (12)	0.0272 (13)	−0.0014 (9)	−0.0013 (9)	−0.0101 (10)
C18	0.0355 (14)	0.0250 (14)	0.0268 (14)	−0.0061 (11)	−0.0062 (11)	−0.0141 (11)
O21	0.0352 (10)	0.0200 (9)	0.0231 (9)	−0.0018 (7)	−0.0041 (7)	−0.0115 (7)
O22	0.0428 (11)	0.0240 (10)	0.0263 (10)	0.0044 (8)	−0.0080 (8)	−0.0092 (8)
N21	0.0230 (10)	0.0177 (10)	0.0229 (10)	−0.0029 (8)	−0.0008 (8)	−0.0085 (8)
C21	0.0180 (11)	0.0156 (12)	0.0226 (12)	−0.0046 (9)	0.0015 (9)	−0.0069 (9)
C22	0.0188 (11)	0.0143 (11)	0.0245 (13)	−0.0006 (9)	−0.0020 (9)	−0.0055 (9)
C23	0.0189 (11)	0.0141 (11)	0.0255 (13)	−0.0034 (9)	0.0011 (9)	−0.0091 (9)
C24	0.0189 (11)	0.0177 (12)	0.0232 (12)	−0.0057 (9)	0.0017 (9)	−0.0079 (9)
C25	0.0182 (11)	0.0145 (12)	0.0258 (13)	−0.0012 (9)	−0.0017 (9)	−0.0055 (9)
C26	0.0201 (11)	0.0132 (11)	0.0270 (13)	−0.0021 (9)	−0.0003 (9)	−0.0093 (9)
C27	0.0217 (12)	0.0173 (12)	0.0263 (13)	−0.0045 (9)	0.0017 (10)	−0.0088 (10)
C28	0.0368 (14)	0.0263 (14)	0.0264 (14)	−0.0043 (11)	−0.0040 (11)	−0.0153 (11)

O11—C17	1.345 (3)	O21—C27	1.342 (3)
O11—C18	1.456 (3)	O21—C28	1.456 (3)
O12—C17	1.215 (3)	O22—C27	1.216 (3)
N11—N11i	1.255 (3)	N21—N21ii	1.257 (4)
N11—C11	1.431 (3)	N21—C21	1.434 (3)
C11—C12	1.391 (3)	C21—C22	1.393 (3)
C11—C16	1.409 (3)	C21—C26	1.411 (3)
C12—C13	1.387 (3)	C22—C23	1.389 (3)
C12—H12	0.9300	C22—H22	0.9300
C13—C14	1.398 (3)	C23—C24	1.401 (3)
C13—H13	0.9300	C23—H23	0.9300
C14—C15	1.398 (3)	C24—C25	1.403 (3)
C14—C17	1.495 (3)	C24—C27	1.491 (3)
C15—C16	1.379 (3)	C25—C26	1.385 (3)
C15—H15	0.9300	C25—H25	0.9300
C16—H16	0.9300	C26—H26	0.9300
C18—H18A	0.9600	C28—H28A	0.9600
C18—H18B	0.9600	C28—H28B	0.9600
C18—H18C	0.9600	C28—H28C	0.9600
C17—O11—C18	116.32 (17)	C27—O21—C28	116.58 (18)
N11i—N11—C11	114.3 (2)	N21ii—N21—C21	114.3 (2)
C12—C11—C16	120.0 (2)	C22—C21—C26	120.4 (2)
C12—C11—N11	115.69 (19)	C22—C21—N21	115.86 (19)
C16—C11—N11	124.25 (19)	C26—C21—N21	123.76 (19)
C13—C12—C11	120.2 (2)	C23—C22—C21	119.7 (2)
C13—C12—H12	119.9	C23—C22—H22	120.2
C11—C12—H12	119.9	C21—C22—H22	120.2
C12—C13—C14	119.88 (19)	C22—C23—C24	120.5 (2)
C12—C13—H13	120.1	C22—C23—H23	119.8
C14—C13—H13	120.1	C24—C23—H23	119.8
C15—C14—C13	119.8 (2)	C23—C24—C25	119.5 (2)
C15—C14—C17	118.83 (19)	C23—C24—C27	121.7 (2)
C13—C14—C17	121.41 (19)	C25—C24—C27	118.8 (2)
C16—C15—C14	120.7 (2)	C26—C25—C24	120.5 (2)
C16—C15—H15	119.7	C26—C25—H25	119.8
C14—C15—H15	119.7	C24—C25—H25	119.8
C15—C16—C11	119.42 (19)	C25—C26—C21	119.4 (2)
C15—C16—H16	120.3	C25—C26—H26	120.3
C11—C16—H16	120.3	C21—C26—H26	120.3
O12—C17—O11	123.6 (2)	O22—C27—O21	123.7 (2)
O12—C17—C14	124.4 (2)	O22—C27—C24	124.4 (2)
O11—C17—C14	111.96 (18)	O21—C27—C24	111.90 (19)
O11—C18—H18A	109.5	O21—C28—H28A	109.5
O11—C18—H18B	109.5	O21—C28—H28B	109.5
H18A—C18—H18B	109.5	H28A—C28—H28B	109.5
O11—C18—H18C	109.5	O21—C28—H28C	109.5
H18A—C18—H18C	109.5	H28A—C28—H28C	109.5
H18B—C18—H18C	109.5	H28B—C28—H28C	109.5
N11i—N11—C11—C12	172.7 (2)	N21ii—N21—C21—C22	−169.5 (2)
N11i—N11—C11—C16	−8.4 (3)	N21ii—N21—C21—C26	10.9 (3)
C16—C11—C12—C13	1.2 (3)	C26—C21—C22—C23	−0.2 (3)
N11—C11—C12—C13	−179.92 (18)	N21—C21—C22—C23	−179.82 (18)
C11—C12—C13—C14	−0.4 (3)	C21—C22—C23—C24	0.1 (3)
C12—C13—C14—C15	−0.4 (3)	C22—C23—C24—C25	0.0 (3)
C12—C13—C14—C17	178.97 (19)	C22—C23—C24—C27	177.82 (19)
C13—C14—C15—C16	0.5 (3)	C23—C24—C25—C26	0.1 (3)
C17—C14—C15—C16	−178.93 (19)	C27—C24—C25—C26	−177.85 (19)
C14—C15—C16—C11	0.3 (3)	C24—C25—C26—C21	−0.1 (3)
C12—C11—C16—C15	−1.1 (3)	C22—C21—C26—C25	0.2 (3)
N11—C11—C16—C15	−179.91 (19)	N21—C21—C26—C25	179.82 (19)
C18—O11—C17—O12	0.8 (3)	C28—O21—C27—O22	1.5 (3)
C18—O11—C17—C14	−178.63 (18)	C28—O21—C27—C24	−178.16 (17)
C15—C14—C17—O12	4.4 (3)	C23—C24—C27—O22	177.8 (2)
C13—C14—C17—O12	−175.0 (2)	C25—C24—C27—O22	−4.3 (3)
C15—C14—C17—O11	−176.20 (18)	C23—C24—C27—O21	−2.5 (3)
C13—C14—C17—O11	4.4 (3)	C25—C24—C27—O21	175.33 (19)