2,2'-Dichloro-1,1'-[(propane-1,3-diyldi-oxy)bis-(nitrilo-methyl-idyne)]dibenzene.

The title compound, C(17)H(16)Cl(2)N(2)O(2), assumes a V-shape configuration with a dihedral angle between the two halves of the mol-ecule of 79.60 (4)°. The asymmetric unit comprises one half-mol-ecule with a crystallographic twofold rotation axis passing through the central C atom. There are weak inter-molecular π-π stacking inter-actions between neighbouring benzene rings with inter-molecular plane-to-plane distances of 3.277 (6) and 3.465 (5) Å along the a and c axes, respectively. In the crystal structure, weak inter-molecular C-H⋯O bonds link each mol-ecule to four others to form an infinite three-dimensional network.

Related literature

For related literature, see: Campbell et al. (2001 ▶); Dong et al. (2006 ▶); Dong, Ding et al. (2008 ▶); Dong, He et al. (2008 ▶); Duan et al. (2007 ▶); Mohand et al. (1995 ▶); Morris et al. (2001 ▶); Shi et al. (2007 ▶).

Experimental

Crystal data

C17H16Cl2N2O2

M = 351.22

Orthorhombic,

a = 6.5218 (7) Å

b = 28.586 (3) Å

c = 4.5120 (6) Å

V = 841.17 (17) Å3

Z = 2

Mo Kα radiation

μ = 0.40 mm−1

T = 298 (2) K

0.45 × 0.18 × 0.15 mm

Data collection

Siemens SMART 1000 CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.842, T max = 0.943

3761 measured reflections

1495 independent reflections

1111 reflections with I > 2σ(I)

R int = 0.047

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.086

S = 1.04

1495 reflections

105 parameters

H-atom parameters constrained

Δρmax = 0.17 e Å−3

Δρmin = −0.17 e Å−3

Absolute structure: Flack (1983 ▶), 565 Friedel pairs

Flack parameter: −0.02 (11)

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/S1600536808021739/fl2205sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808021739/fl2205Isup2.hkl

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

C17H16Cl2N2O2	F000 = 364
Mr = 351.22	Dx = 1.387 Mg m−3
Orthorhombic, P21212	Mo Kα radiation λ = 0.71073 Å
Hall symbol: P 2 2ab	Cell parameters from 1292 reflections
a = 6.5218 (7) Å	θ = 2.9–22.2º
b = 28.586 (3) Å	µ = 0.40 mm−1
c = 4.5120 (6) Å	T = 298 (2) K
V = 841.17 (17) Å3	Needle-like, colorless
Z = 2	0.45 × 0.18 × 0.15 mm

Siemens SMART 1000 CCD area-detector diffractometer	1495 independent reflections
Radiation source: fine-focus sealed tube	1111 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.047
T = 298(2) K	θmax = 25.0º
φ and ω scans	θmin = 1.4º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)	h = −7→7
Tmin = 0.842, Tmax = 0.943	k = −17→34
3761 measured reflections	l = −5→5

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.042	w = 1/[σ2(Fo2) + (0.0338P)2] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.086	(Δ/σ)max < 0.001
S = 1.05	Δρmax = 0.17 e Å−3
1495 reflections	Δρmin = −0.17 e Å−3
105 parameters	Extinction correction: none
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 565 Friedel pairs
Secondary atom site location: difference Fourier map	Flack parameter: −0.02 (11)

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)
Cl1	0.68069 (12)	0.20827 (3)	0.4175 (2)	0.0826 (3)
N1	0.8042 (3)	0.06911 (7)	0.7415 (5)	0.0441 (5)
O1	0.6419 (2)	0.05622 (5)	0.9278 (5)	0.0502 (5)
C1	0.6858 (3)	0.01262 (8)	1.0698 (6)	0.0454 (6)
H1A	0.8046	0.0157	1.1976	0.054*
H1B	0.7137	−0.0114	0.9232	0.054*
C2	0.5000	0.0000	1.2484 (8)	0.0435 (10)
H2A	0.5342	−0.0262	1.3754	0.052*	0.50
H2B	0.4658	0.0262	1.3754	0.052*	0.50
C3	0.7749 (4)	0.10932 (8)	0.6332 (6)	0.0489 (8)
H3	0.6573	0.1258	0.6850	0.059*
C4	0.9206 (3)	0.13043 (8)	0.4297 (7)	0.0414 (6)
C5	0.8922 (4)	0.17493 (9)	0.3130 (7)	0.0467 (8)
C6	1.0293 (5)	0.19465 (9)	0.1179 (7)	0.0583 (8)
H6	1.0059	0.2245	0.0427	0.070*
C7	1.2002 (5)	0.17021 (10)	0.0352 (8)	0.0674 (9)
H7	1.2933	0.1832	−0.0975	0.081*
C8	1.2334 (4)	0.12619 (10)	0.1497 (7)	0.0650 (9)
H8	1.3500	0.1096	0.0950	0.078*
C9	1.0964 (4)	0.10670 (9)	0.3433 (7)	0.0542 (8)
H9	1.1216	0.0770	0.4185	0.065*

	U11	U22	U33	U12	U13	U23
Cl1	0.0880 (6)	0.0630 (5)	0.0967 (7)	0.0250 (4)	0.0168 (6)	0.0231 (5)
N1	0.0454 (12)	0.0429 (12)	0.0439 (13)	−0.0079 (11)	0.0078 (13)	−0.0029 (12)
O1	0.0508 (10)	0.0440 (9)	0.0559 (12)	−0.0012 (8)	0.0120 (11)	0.0089 (10)
C1	0.0526 (14)	0.0393 (13)	0.0443 (16)	−0.0049 (13)	−0.0008 (17)	0.0024 (14)
C2	0.053 (2)	0.039 (2)	0.038 (2)	−0.0065 (17)	0.000	0.000
C3	0.0517 (15)	0.0422 (14)	0.053 (2)	0.0016 (12)	0.0094 (16)	0.0028 (15)
C4	0.0450 (13)	0.0407 (13)	0.0384 (16)	−0.0069 (11)	−0.0002 (14)	−0.0028 (14)
C5	0.0566 (16)	0.0401 (13)	0.043 (2)	−0.0058 (13)	−0.0002 (14)	−0.0009 (14)
C6	0.079 (2)	0.0477 (16)	0.048 (2)	−0.0134 (16)	−0.0004 (18)	0.0070 (17)
C7	0.0670 (19)	0.073 (2)	0.063 (2)	−0.0248 (17)	0.019 (2)	0.0038 (19)
C8	0.0588 (18)	0.0610 (17)	0.075 (3)	−0.0040 (15)	0.0171 (18)	−0.0052 (19)
C9	0.0550 (15)	0.0454 (14)	0.062 (2)	−0.0001 (13)	0.0108 (16)	−0.0042 (16)

Cl1—C5	1.742 (3)	C3—H3	0.9300
N1—C3	1.264 (3)	C4—C9	1.388 (3)
N1—O1	1.401 (2)	C4—C5	1.389 (3)
O1—C1	1.430 (3)	C5—C6	1.376 (4)
C1—C2	1.499 (3)	C6—C7	1.367 (4)
C1—H1A	0.9700	C6—H6	0.9300
C1—H1B	0.9700	C7—C8	1.377 (4)
C2—C1i	1.499 (3)	C7—H7	0.9300
C2—H2A	0.9700	C8—C9	1.368 (4)
C2—H2B	0.9700	C8—H8	0.9300
C3—C4	1.453 (3)	C9—H9	0.9300
C3—N1—O1	110.9 (2)	C9—C4—C3	121.0 (2)
N1—O1—C1	110.30 (16)	C5—C4—C3	122.2 (2)
O1—C1—C2	106.78 (17)	C6—C5—C4	122.1 (3)
O1—C1—H1A	110.4	C6—C5—Cl1	117.6 (2)
C2—C1—H1A	110.4	C4—C5—Cl1	120.3 (2)
O1—C1—H1B	110.4	C7—C6—C5	119.7 (3)
C2—C1—H1B	110.4	C7—C6—H6	120.2
H1A—C1—H1B	108.6	C5—C6—H6	120.2
C1i—C2—C1	115.0 (3)	C6—C7—C8	119.5 (3)
C1i—C2—H2A	108.5	C6—C7—H7	120.3
C1—C2—H2A	108.5	C8—C7—H7	120.3
C1i—C2—H2B	108.5	C9—C8—C7	120.6 (3)
C1—C2—H2B	108.5	C9—C8—H8	119.7
H2A—C2—H2B	107.5	C7—C8—H8	119.7
N1—C3—C4	121.6 (2)	C8—C9—C4	121.3 (3)
N1—C3—H3	119.2	C8—C9—H9	119.3
C4—C3—H3	119.2	C4—C9—H9	119.3
C9—C4—C5	116.8 (3)
C3—N1—O1—C1	−174.7 (2)	C3—C4—C5—Cl1	2.0 (4)
N1—O1—C1—C2	−176.4 (2)	C4—C5—C6—C7	−0.3 (4)
O1—C1—C2—C1i	68.74 (16)	Cl1—C5—C6—C7	178.4 (2)
O1—N1—C3—C4	−179.3 (2)	C5—C6—C7—C8	−0.4 (5)
N1—C3—C4—C9	1.0 (4)	C6—C7—C8—C9	0.5 (5)
N1—C3—C4—C5	−178.8 (3)	C7—C8—C9—C4	0.1 (4)
C9—C4—C5—C6	0.8 (4)	C5—C4—C9—C8	−0.7 (4)
C3—C4—C5—C6	−179.3 (2)	C3—C4—C9—C8	179.4 (2)
C9—C4—C5—Cl1	−177.9 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8···O1ii	0.93	2.55	3.479 (3)	173

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8⋯O1i	0.93	2.55	3.479 (3)	173

Symmetry code: (i) .