3,3'-Dibromo-1,1'-[(propane-1,3-diyl-dioxy)-bis(nitrilo-methyl-idyne)]dibenzene.

The mol-ecule of the title compound, C(17)H(16)Br(2)N(2)O(2), lies on a twofold axis that passes through the middle atom of the three-atom trimethyl-ene unit. The two aromatic rings are aligned at an angle of 76.02 (4)°.

Related literature

For similar Schiff bases, see: Aysegul et al. (2005 ▶); Cordes & Jencks (1962 ▶); Dong et al. (2008 ▶); Duan et al. (2007 ▶); Shi et al. (2007 ▶); Koehler et al. (1964 ▶).

Experimental

Crystal data

C17H16Br2N2O2

M = 440.14

Monoclinic,

a = 24.397 (3) Å

b = 4.4848 (4) Å

c = 17.189 (2) Å

β = 114.009 (2)°

V = 1718.0 (3) Å3

Z = 4

Mo Kα radiation

μ = 4.73 mm−1

T = 298 (2) K

0.48 × 0.35 × 0.24 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.210, T max = 0.397 (expected range = 0.170–0.321)

3683 measured reflections

1497 independent reflections

1179 reflections with I > 2σ(I)

R int = 0.094

Refinement

R[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.133

S = 1.07

1497 reflections

105 parameters

H-atom parameters constrained

Δρmax = 0.60 e Å−3

Δρmin = −0.66 e Å−3

Data collection: SMART (Bruker, 1996 ▶); cell refinement: SAINT (Bruker, 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/S1600536808018187/ng2462sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808018187/ng2462Isup2.hkl

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

C17H16Br2N2O2	F000 = 872
Mr = 440.14	Dx = 1.702 Mg m−3
Monoclinic, C2/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 2255 reflections
a = 24.397 (3) Å	θ = 2.5–27.9º
b = 4.4848 (4) Å	µ = 4.73 mm−1
c = 17.189 (2) Å	T = 298 (2) K
β = 114.009 (2)º	Rod, colorless
V = 1718.0 (3) Å3	0.48 × 0.35 × 0.24 mm
Z = 4

Bruker SMART 1000 CCD area-detector diffractometer	1497 independent reflections
Radiation source: fine-focus sealed tube	1179 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.094
T = 298(2) K	θmax = 25.0º
φ and ω scans	θmin = 1.8º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)	h = −27→28
Tmin = 0.210, Tmax = 0.397	k = −5→5
3683 measured reflections	l = −20→15

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)] = 0.050	H-atom parameters constrained
wR(F2) = 0.133	w = 1/[σ2(Fo2) + (0.061P)2] where P = (Fo2 + 2Fc2)/3
S = 1.07	(Δ/σ)max = 0.001
1497 reflections	Δρmax = 0.60 e Å−3
105 parameters	Δρmin = −0.66 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	Occ. (<1)
Br1	0.78652 (2)	1.12437 (15)	0.11896 (3)	0.0608 (3)
O1	0.53639 (12)	0.3149 (7)	−0.13426 (18)	0.0393 (8)
N1	0.58506 (15)	0.4899 (10)	−0.0798 (2)	0.0352 (9)
C1	0.5538 (2)	0.1605 (10)	−0.1934 (3)	0.0369 (11)
H1A	0.5876	0.0299	−0.1635	0.044*
H1B	0.5653	0.3011	−0.2270	0.044*
C2	0.5000	−0.0186 (16)	−0.2500	0.0371 (15)
H2A	0.4880	−0.1465	−0.2142	0.044*	0.50
H2B	0.5120	−0.1465	−0.2858	0.044*	0.50
C3	0.5704 (2)	0.6276 (10)	−0.0265 (3)	0.0398 (12)
H3	0.5317	0.6039	−0.0296	0.048*
C4	0.6117 (2)	0.8206 (10)	0.0390 (3)	0.0350 (11)
C5	0.6701 (2)	0.8759 (10)	0.0463 (3)	0.0368 (11)
H5	0.6836	0.7885	0.0083	0.044*
C6	0.7070 (2)	1.0573 (11)	0.1091 (3)	0.0391 (12)
C7	0.6887 (2)	1.1924 (12)	0.1666 (3)	0.0472 (13)
H7	0.7144	1.3178	0.2087	0.057*
C8	0.6313 (3)	1.1373 (11)	0.1600 (3)	0.0504 (14)
H8	0.6185	1.2245	0.1988	0.061*
C9	0.5930 (2)	0.9556 (12)	0.0972 (3)	0.0444 (13)
H9	0.5544	0.9222	0.0935	0.053*

	U11	U22	U33	U12	U13	U23
Br1	0.0451 (4)	0.0844 (6)	0.0468 (4)	−0.0215 (3)	0.0126 (3)	−0.0037 (3)
O1	0.0346 (18)	0.042 (2)	0.0377 (19)	−0.0112 (15)	0.0110 (15)	−0.0071 (16)
N1	0.030 (2)	0.036 (2)	0.033 (2)	−0.0059 (17)	0.0067 (17)	0.0016 (19)
C1	0.038 (3)	0.036 (3)	0.035 (2)	0.003 (2)	0.014 (2)	0.007 (2)
C2	0.039 (4)	0.026 (4)	0.043 (4)	0.000	0.013 (3)	0.000
C3	0.037 (3)	0.040 (3)	0.039 (3)	−0.009 (2)	0.012 (2)	0.002 (2)
C4	0.040 (3)	0.035 (3)	0.029 (2)	0.000 (2)	0.013 (2)	0.009 (2)
C5	0.040 (3)	0.041 (3)	0.027 (2)	−0.001 (2)	0.012 (2)	0.003 (2)
C6	0.043 (3)	0.044 (3)	0.026 (2)	−0.006 (2)	0.009 (2)	0.005 (2)
C7	0.059 (3)	0.042 (3)	0.030 (2)	−0.007 (3)	0.008 (2)	−0.005 (2)
C8	0.066 (4)	0.052 (4)	0.041 (3)	0.001 (3)	0.029 (3)	−0.007 (3)
C9	0.047 (3)	0.040 (3)	0.050 (3)	0.000 (2)	0.024 (3)	0.001 (3)

Br1—C6	1.900 (4)	C3—H3	0.9300
O1—N1	1.413 (4)	C4—C9	1.396 (6)
O1—C1	1.431 (5)	C4—C5	1.400 (6)
N1—C3	1.270 (6)	C5—C6	1.359 (6)
C1—C2	1.508 (6)	C5—H5	0.9300
C1—H1A	0.9700	C6—C7	1.381 (6)
C1—H1B	0.9700	C7—C8	1.379 (7)
C2—C1i	1.508 (6)	C7—H7	0.9300
C2—H2A	0.9700	C8—C9	1.372 (7)
C2—H2B	0.9700	C8—H8	0.9300
C3—C4	1.453 (6)	C9—H9	0.9300
N1—O1—C1	109.1 (3)	C9—C4—C3	119.2 (4)
C3—N1—O1	109.9 (3)	C5—C4—C3	122.3 (4)
O1—C1—C2	106.5 (3)	C6—C5—C4	120.0 (4)
O1—C1—H1A	110.4	C6—C5—H5	120.0
C2—C1—H1A	110.4	C4—C5—H5	120.0
O1—C1—H1B	110.4	C5—C6—C7	121.8 (4)
C2—C1—H1B	110.4	C5—C6—Br1	119.3 (3)
H1A—C1—H1B	108.6	C7—C6—Br1	118.9 (4)
C1—C2—C1i	115.7 (5)	C8—C7—C6	118.5 (5)
C1—C2—H2A	108.4	C8—C7—H7	120.8
C1i—C2—H2A	108.4	C6—C7—H7	120.8
C1—C2—H2B	108.4	C9—C8—C7	121.0 (4)
C1i—C2—H2B	108.4	C9—C8—H8	119.5
H2A—C2—H2B	107.4	C7—C8—H8	119.5
N1—C3—C4	122.6 (4)	C8—C9—C4	120.3 (4)
N1—C3—H3	118.7	C8—C9—H9	119.8
C4—C3—H3	118.7	C4—C9—H9	119.8
C9—C4—C5	118.4 (4)
C1—O1—N1—C3	−179.7 (4)	C4—C5—C6—C7	−0.3 (7)
N1—O1—C1—C2	−179.4 (4)	C4—C5—C6—Br1	179.0 (3)
O1—C1—C2—C1i	65.8 (3)	C5—C6—C7—C8	0.7 (7)
O1—N1—C3—C4	178.7 (4)	Br1—C6—C7—C8	−178.6 (4)
N1—C3—C4—C9	−177.6 (4)	C6—C7—C8—C9	−0.8 (8)
N1—C3—C4—C5	2.1 (7)	C7—C8—C9—C4	0.6 (8)
C9—C4—C5—C6	0.0 (6)	C5—C4—C9—C8	−0.1 (7)
C3—C4—C5—C6	−179.7 (4)	C3—C4—C9—C8	179.6 (5)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H3···C3#	0.93	2.36	3.189	148