3,3'-Dibromo-1,1'-[ethyl-enedioxy-bis(nitrilo-methyl-idyne)]dibenzene.

In the centrosymmetric title compound, C(16)H(14)Br(2)N(2)O(2), the intra-molecular interplanar distance between the parallel benzene rings is 1.305 (3) Å, while the inter-molecular interplanar distance (between neighbouring mol-ecules) is 3.463 (3) Å, exhibiting obvious strong inter-molecular π-π stacking inter-actions.

Related literature

For related literature, see: Akine et al. (2006 ▶); Atwood & Harvey (2001 ▶); Dong & Duan (2008 ▶); Dong et al. (2007 ▶); Dong, Duan et al. (2008 ▶); Dong, Shi et al. (2008 ▶); Katsuki (1995 ▶); Sun et al. (2004 ▶).

Experimental

Crystal data

C16H14Br2N2O2

M = 426.11

Monoclinic,

a = 4.5072 (7) Å

b = 7.615 (2) Å

c = 23.180 (3) Å

β = 93.523 (2)°

V = 794.1 (3) Å3

Z = 2

Mo Kα radiation

μ = 5.11 mm−1

T = 298 (2) K

0.42 × 0.27 × 0.15 mm

Data collection

Siemens SMART 1000 CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.223, T max = 0.514 (expected range = 0.201–0.464)

3840 measured reflections

1400 independent reflections

1168 reflections with I > 2σ(I)

R int = 0.043

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.097

S = 1.04

1400 reflections

100 parameters

H-atom parameters constrained

Δρmax = 0.28 e Å−3

Δρmin = −0.49 e Å−3

Data collection: SMART (Siemens, 1996 ▶); cell refinement: SAINT (Siemens, 1996 ▶); data reduction: SAINT; 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 datablocks global, I. DOI: 10.1107/S1600536808020692/ww2122sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808020692/ww2122Isup2.hkl

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

C16H14Br2N2O2	F000 = 420
Mr = 426.11	Dx = 1.782 Mg m−3
Monoclinic, P21/n	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2000 reflections
a = 4.5072 (7) Å	θ = 2.6–26.7º
b = 7.615 (2) Å	µ = 5.11 mm−1
c = 23.180 (3) Å	T = 298 (2) K
β = 93.523 (2)º	Needle-shaped, colorless
V = 794.1 (3) Å3	0.42 × 0.27 × 0.15 mm
Z = 2

Siemens SMART 1000 CCD area-detector diffractometer	1400 independent reflections
Radiation source: fine-focus sealed tube	1168 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.043
T = 298(2) K	θmax = 25.0º
ω and φ scans	θmin = 1.8º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)	h = −5→5
Tmin = 0.223, Tmax = 0.514	k = −8→9
3840 measured reflections	l = −19→27

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.037	H-atom parameters constrained
wR(F2) = 0.097	w = 1/[σ2(Fo2) + (0.0535P)2 + 0.3108P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max < 0.001
1400 reflections	Δρmax = 0.28 e Å−3
100 parameters	Δρmin = −0.49 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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
Br1	0.56056 (10)	0.86904 (5)	0.160074 (19)	0.0576 (2)
N1	−0.2668 (6)	0.2442 (4)	0.05861 (13)	0.0381 (7)
O1	−0.4716 (6)	0.2385 (3)	0.00969 (11)	0.0422 (6)
C1	−0.6114 (8)	0.0710 (5)	0.00676 (17)	0.0396 (8)
H1A	−0.7723	0.0722	−0.0230	0.048*
H1B	−0.6952	0.0452	0.0434	0.048*
C2	−0.1591 (8)	0.3960 (4)	0.06447 (16)	0.0373 (8)
H2	−0.2198	0.4837	0.0384	0.045*
C3	0.0595 (7)	0.4362 (4)	0.11157 (15)	0.0324 (8)
C4	0.1868 (8)	0.6001 (4)	0.11401 (15)	0.0350 (8)
H4	0.1337	0.6827	0.0857	0.042*
C5	0.3929 (8)	0.6427 (4)	0.15821 (16)	0.0369 (8)
C6	0.4796 (9)	0.5227 (5)	0.19990 (16)	0.0449 (9)
H6	0.6198	0.5523	0.2294	0.054*
C7	0.3545 (9)	0.3565 (5)	0.19728 (18)	0.0485 (10)
H7	0.4098	0.2741	0.2256	0.058*
C8	0.1504 (9)	0.3121 (5)	0.15356 (16)	0.0412 (9)
H8	0.0719	0.1992	0.1517	0.049*

	U11	U22	U33	U12	U13	U23
Br1	0.0701 (4)	0.0416 (3)	0.0597 (3)	−0.0158 (2)	−0.0076 (2)	−0.00700 (18)
N1	0.0374 (16)	0.0381 (17)	0.0381 (18)	−0.0031 (13)	−0.0038 (13)	−0.0018 (13)
O1	0.0438 (14)	0.0346 (13)	0.0468 (15)	−0.0078 (11)	−0.0083 (12)	0.0016 (11)
C1	0.037 (2)	0.0389 (19)	0.043 (2)	−0.0032 (16)	−0.0004 (16)	−0.0033 (16)
C2	0.0387 (19)	0.0329 (19)	0.040 (2)	0.0004 (15)	0.0022 (16)	0.0032 (15)
C3	0.0310 (18)	0.0343 (18)	0.0323 (19)	0.0008 (14)	0.0061 (14)	−0.0021 (14)
C4	0.039 (2)	0.0322 (18)	0.0337 (19)	0.0024 (15)	0.0026 (15)	−0.0001 (14)
C5	0.038 (2)	0.0344 (19)	0.038 (2)	−0.0041 (15)	0.0036 (16)	−0.0037 (15)
C6	0.047 (2)	0.049 (2)	0.037 (2)	0.0008 (18)	−0.0054 (18)	−0.0027 (17)
C7	0.052 (2)	0.046 (2)	0.047 (2)	0.0059 (19)	−0.0024 (19)	0.0120 (18)
C8	0.048 (2)	0.0334 (19)	0.043 (2)	−0.0055 (17)	0.0102 (18)	0.0027 (16)

Br1—C5	1.881 (3)	C3—C8	1.399 (5)
N1—C2	1.258 (4)	C4—C5	1.379 (5)
N1—O1	1.418 (4)	C4—H4	0.9300
O1—C1	1.423 (4)	C5—C6	1.369 (5)
C1—C1i	1.521 (7)	C6—C7	1.386 (5)
C1—H1A	0.9700	C6—H6	0.9300
C1—H1B	0.9700	C7—C8	1.368 (5)
C2—C3	1.457 (5)	C7—H7	0.9300
C2—H2	0.9300	C8—H8	0.9300
C3—C4	1.373 (5)
C2—N1—O1	110.0 (3)	C3—C4—H4	119.8
N1—O1—C1	109.3 (3)	C5—C4—H4	119.8
O1—C1—C1i	110.5 (4)	C6—C5—C4	121.1 (3)
O1—C1—H1A	109.5	C6—C5—Br1	119.9 (3)
C1i—C1—H1A	109.5	C4—C5—Br1	119.0 (3)
O1—C1—H1B	109.5	C5—C6—C7	118.8 (3)
C1i—C1—H1B	109.5	C5—C6—H6	120.6
H1A—C1—H1B	108.1	C7—C6—H6	120.6
N1—C2—C3	120.8 (3)	C8—C7—C6	120.7 (4)
N1—C2—H2	119.6	C8—C7—H7	119.6
C3—C2—H2	119.6	C6—C7—H7	119.6
C4—C3—C8	118.7 (3)	C7—C8—C3	120.2 (4)
C4—C3—C2	118.9 (3)	C7—C8—H8	119.9
C8—C3—C2	122.3 (3)	C3—C8—H8	119.9
C3—C4—C5	120.4 (3)
C2—N1—O1—C1	−174.7 (3)	C3—C4—C5—Br1	−179.8 (3)
N1—O1—C1—C1i	−67.7 (5)	C4—C5—C6—C7	−0.5 (6)
O1—N1—C2—C3	−179.6 (3)	Br1—C5—C6—C7	−179.5 (3)
N1—C2—C3—C4	175.5 (3)	C5—C6—C7—C8	0.7 (6)
N1—C2—C3—C8	−2.8 (5)	C6—C7—C8—C3	−1.6 (6)
C8—C3—C4—C5	−2.1 (5)	C4—C3—C8—C7	2.3 (6)
C2—C3—C4—C5	179.6 (3)	C2—C3—C8—C7	−179.4 (4)
C3—C4—C5—C6	1.2 (5)