2,2'-Dichloro-1,1'-[(pentane-1,5-diyldi-oxy)bis-(nitrilo-methyl-idyne)]dibenzene.

The mol-ecule of the title compound, C(19)H(20)Cl(2)N(2)O(2), which lies across a crystallographic inversion centre, adopts a linear configuration. The dihedral angle between the two halves of the mol-ecule is 5.14 (2)°. In the crystal structure, inter-molecular C-H⋯O hydrogen bonds link neighbouring mol-ecules into an infinite zigzag chain supra-molecular structure.

Related literature

For background to Schiff base compounds in transition n class="Chemical">metal coordination chemistry, see: Granovski et al. (1993 ▶). For the properties of Schiff base–metal complexes, see: Ghosh et al. (2006 ▶); Ward (2007 ▶). For our work on the synthesis and structural characterization of Schiff base–bis­oxime compounds, see: Dong et al. (2008a ▶). For related structures, see: Dong et al. (2008b ▶, 2009 ▶); Sun et al. (2009 ▶).

Experimental

Crystal data

C19H20Cl2N2O2

M = 379.27

Monoclinic,

a = 12.5025 (12) Å

b = 19.7801 (17) Å

c = 7.8085 (9) Å

β = 96.747 (1)°

V = 1917.7 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.35 mm−1

T = 298 K

0.45 × 0.30 × 0.28 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.857, T max = 0.908

9529 measured reflections

3376 independent reflections

1631 reflections with I > 2σ(I)

R int = 0.048

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.116

S = 1.02

3376 reflections

226 parameters

H-atom parameters constrained

Δρmax = 0.21 e Å−3

Δρmin = −0.25 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/S1600536809027433/hg2535sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809027433/hg2535Isup2.hkl

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

C19H20Cl2N2O2	F(000) = 792
Mr = 379.27	Dx = 1.314 Mg m−3
Monoclinic, P21/c	Melting point = 327–328 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 12.5025 (12) Å	Cell parameters from 1696 reflections
b = 19.7801 (17) Å	θ = 2.6–21.6°
c = 7.8085 (9) Å	µ = 0.35 mm−1
β = 96.747 (1)°	T = 298 K
V = 1917.7 (3) Å3	Needle-like, colorless
Z = 4	0.45 × 0.30 × 0.28 mm

Bruker SMART CCD area-detector diffractometer	3376 independent reflections
Radiation source: fine-focus sealed tube	1631 reflections with I > 2σ(I)
graphite	Rint = 0.048
φ and ω scans	θmax = 25.0°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→14
Tmin = 0.857, Tmax = 0.908	k = −23→19
9529 measured reflections	l = −9→9

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.116	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0407P)2 + 0.181P] where P = (Fo2 + 2Fc2)/3
3376 reflections	(Δ/σ)max = 0.001
226 parameters	Δρmax = 0.21 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
Cl1	1.35447 (6)	0.01799 (4)	0.52460 (14)	0.0757 (4)
Cl2	0.26416 (7)	0.37373 (5)	−0.36888 (13)	0.0750 (3)
N1	1.03773 (19)	−0.03387 (13)	0.2814 (3)	0.0518 (7)
N2	0.38680 (19)	0.17370 (14)	−0.2572 (3)	0.0548 (8)
O1	0.98008 (15)	0.02573 (10)	0.2391 (3)	0.0561 (6)
O2	0.48710 (16)	0.18002 (11)	−0.1578 (3)	0.0676 (7)
C1	0.8763 (2)	0.00878 (16)	0.1514 (4)	0.0547 (9)
H1A	0.8361	−0.0179	0.2260	0.066*
H1B	0.8844	−0.0175	0.0488	0.066*
C2	0.8178 (2)	0.07350 (15)	0.1030 (4)	0.0500 (9)
H2A	0.8567	0.0985	0.0231	0.060*
H2B	0.8159	0.1010	0.2054	0.060*
C3	0.7034 (2)	0.06076 (15)	0.0203 (4)	0.0508 (9)
H3A	0.7054	0.0333	−0.0823	0.061*
H3B	0.6646	0.0357	0.1000	0.061*
C4	0.6438 (2)	0.12609 (15)	−0.0285 (4)	0.0514 (9)
H4A	0.6416	0.1533	0.0744	0.062*
H4B	0.6833	0.1513	−0.1071	0.062*
C5	0.5302 (2)	0.11490 (16)	−0.1123 (4)	0.0572 (10)
H5A	0.5302	0.0868	−0.2141	0.069*
H5B	0.4876	0.0927	−0.0327	0.069*
C6	1.1294 (2)	−0.02145 (15)	0.3602 (4)	0.0478 (9)
H6	1.1501	0.0231	0.3829	0.057*
C7	1.2036 (2)	−0.07616 (16)	0.4163 (4)	0.0427 (8)
C8	1.3086 (2)	−0.06409 (15)	0.4923 (4)	0.0481 (8)
C9	1.3784 (2)	−0.11648 (18)	0.5446 (4)	0.0592 (10)
H9	1.4480	−0.1071	0.5947	0.071*
C10	1.3447 (3)	−0.18221 (19)	0.5225 (5)	0.0696 (11)
H10	1.3913	−0.2176	0.5573	0.084*
C11	1.2412 (3)	−0.19537 (18)	0.4484 (5)	0.0693 (11)
H11	1.2182	−0.2399	0.4323	0.083*
C12	1.1719 (2)	−0.14340 (17)	0.3981 (4)	0.0551 (9)
H12	1.1020	−0.1534	0.3506	0.066*
C13	0.3452 (2)	0.23100 (17)	−0.2923 (4)	0.0554 (10)
H13	0.3823	0.2697	−0.2528	0.066*
C14	0.2399 (2)	0.23755 (16)	−0.3936 (4)	0.0434 (8)
C15	0.1946 (2)	0.30034 (15)	−0.4349 (4)	0.0473 (8)
C16	0.0941 (3)	0.30657 (19)	−0.5273 (4)	0.0618 (10)
H16	0.0650	0.3491	−0.5532	0.074*
C17	0.0375 (3)	0.2494 (2)	−0.5807 (5)	0.0651 (11)
H17	−0.0305	0.2533	−0.6427	0.078*
C18	0.0805 (3)	0.18646 (19)	−0.5430 (4)	0.0618 (10)
H18	0.0420	0.1479	−0.5802	0.074*
C19	0.1803 (2)	0.18066 (16)	−0.4505 (4)	0.0548 (9)
H19	0.2088	0.1379	−0.4253	0.066*

	U11	U22	U33	U12	U13	U23
Cl1	0.0486 (5)	0.0534 (6)	0.1195 (9)	−0.0057 (4)	−0.0139 (5)	0.0063 (6)
Cl2	0.0702 (6)	0.0465 (6)	0.1062 (8)	0.0037 (4)	0.0024 (5)	0.0050 (5)
N1	0.0426 (17)	0.0486 (18)	0.061 (2)	0.0090 (13)	−0.0089 (14)	0.0017 (15)
N2	0.0388 (16)	0.0545 (19)	0.068 (2)	0.0067 (13)	−0.0065 (14)	0.0003 (16)
O1	0.0426 (13)	0.0461 (15)	0.0745 (17)	0.0089 (10)	−0.0153 (11)	−0.0005 (12)
O2	0.0467 (14)	0.0513 (15)	0.097 (2)	0.0068 (11)	−0.0232 (13)	0.0020 (14)
C1	0.0383 (18)	0.057 (2)	0.065 (2)	0.0020 (16)	−0.0098 (17)	0.0033 (19)
C2	0.048 (2)	0.046 (2)	0.054 (2)	0.0081 (15)	−0.0018 (16)	0.0015 (17)
C3	0.0424 (19)	0.050 (2)	0.056 (2)	0.0040 (15)	−0.0075 (16)	0.0031 (18)
C4	0.047 (2)	0.052 (2)	0.053 (2)	0.0066 (16)	−0.0069 (16)	0.0019 (18)
C5	0.047 (2)	0.051 (2)	0.070 (3)	0.0118 (16)	−0.0080 (18)	0.0019 (19)
C6	0.0413 (19)	0.041 (2)	0.059 (2)	0.0021 (16)	−0.0035 (17)	0.0016 (18)
C7	0.0390 (19)	0.044 (2)	0.045 (2)	0.0003 (15)	0.0024 (15)	0.0028 (16)
C8	0.0434 (19)	0.046 (2)	0.054 (2)	−0.0009 (16)	0.0019 (16)	0.0038 (17)
C9	0.041 (2)	0.058 (3)	0.076 (3)	0.0084 (17)	−0.0022 (18)	0.010 (2)
C10	0.063 (3)	0.054 (3)	0.088 (3)	0.0170 (19)	−0.005 (2)	0.014 (2)
C11	0.067 (3)	0.047 (2)	0.091 (3)	0.0034 (19)	−0.006 (2)	0.000 (2)
C12	0.043 (2)	0.051 (2)	0.068 (3)	−0.0020 (16)	−0.0066 (17)	0.0000 (19)
C13	0.049 (2)	0.041 (2)	0.074 (3)	0.0053 (16)	−0.0004 (19)	0.0019 (19)
C14	0.0370 (19)	0.049 (2)	0.044 (2)	0.0076 (16)	0.0047 (15)	0.0023 (17)
C15	0.048 (2)	0.044 (2)	0.051 (2)	0.0067 (16)	0.0080 (17)	0.0059 (17)
C16	0.053 (2)	0.058 (3)	0.073 (3)	0.0161 (19)	0.0045 (19)	0.015 (2)
C17	0.047 (2)	0.080 (3)	0.066 (3)	0.008 (2)	−0.0041 (19)	0.013 (2)
C18	0.051 (2)	0.066 (3)	0.067 (3)	0.0014 (18)	−0.0002 (19)	−0.005 (2)
C19	0.050 (2)	0.048 (2)	0.065 (3)	0.0079 (17)	−0.0004 (18)	0.0007 (19)

Cl1—C8	1.731 (3)	C6—H6	0.9300
Cl2—C15	1.739 (3)	C7—C12	1.390 (4)
N1—C6	1.260 (3)	C7—C8	1.396 (4)
N1—O1	1.401 (3)	C8—C9	1.385 (4)
N2—C13	1.264 (3)	C9—C10	1.371 (4)
N2—O2	1.401 (3)	C9—H9	0.9300
O1—C1	1.434 (3)	C10—C11	1.379 (4)
O2—C5	1.425 (3)	C10—H10	0.9300
C1—C2	1.500 (4)	C11—C12	1.371 (4)
C1—H1A	0.9700	C11—H11	0.9300
C1—H1B	0.9700	C12—H12	0.9300
C2—C3	1.520 (4)	C13—C14	1.459 (4)
C2—H2A	0.9700	C13—H13	0.9300
C2—H2B	0.9700	C14—C15	1.387 (4)
C3—C4	1.518 (4)	C14—C19	1.393 (4)
C3—H3A	0.9700	C15—C16	1.378 (4)
C3—H3B	0.9700	C16—C17	1.373 (4)
C4—C5	1.508 (3)	C16—H16	0.9300
C4—H4A	0.9700	C17—C18	1.374 (4)
C4—H4B	0.9700	C17—H17	0.9300
C5—H5A	0.9700	C18—C19	1.371 (4)
C5—H5B	0.9700	C18—H18	0.9300
C6—C7	1.459 (4)	C19—H19	0.9300
C6—N1—O1	111.4 (2)	C12—C7—C6	121.1 (3)
C13—N2—O2	111.0 (3)	C8—C7—C6	122.2 (3)
N1—O1—C1	109.1 (2)	C9—C8—C7	121.7 (3)
N2—O2—C5	110.2 (2)	C9—C8—Cl1	118.2 (2)
O1—C1—C2	107.9 (2)	C7—C8—Cl1	120.1 (2)
O1—C1—H1A	110.1	C10—C9—C8	119.9 (3)
C2—C1—H1A	110.1	C10—C9—H9	120.0
O1—C1—H1B	110.1	C8—C9—H9	120.0
C2—C1—H1B	110.1	C9—C10—C11	119.4 (3)
H1A—C1—H1B	108.4	C9—C10—H10	120.3
C1—C2—C3	111.9 (2)	C11—C10—H10	120.3
C1—C2—H2A	109.2	C12—C11—C10	120.6 (3)
C3—C2—H2A	109.2	C12—C11—H11	119.7
C1—C2—H2B	109.2	C10—C11—H11	119.7
C3—C2—H2B	109.2	C11—C12—C7	121.7 (3)
H2A—C2—H2B	107.9	C11—C12—H12	119.2
C4—C3—C2	112.1 (2)	C7—C12—H12	119.2
C4—C3—H3A	109.2	N2—C13—C14	121.3 (3)
C2—C3—H3A	109.2	N2—C13—H13	119.4
C4—C3—H3B	109.2	C14—C13—H13	119.4
C2—C3—H3B	109.2	C15—C14—C19	117.4 (3)
H3A—C3—H3B	107.9	C15—C14—C13	121.5 (3)
C5—C4—C3	113.2 (2)	C19—C14—C13	121.0 (3)
C5—C4—H4A	108.9	C16—C15—C14	121.6 (3)
C3—C4—H4A	108.9	C16—C15—Cl2	118.3 (3)
C5—C4—H4B	108.9	C14—C15—Cl2	120.1 (2)
C3—C4—H4B	108.9	C17—C16—C15	119.4 (3)
H4A—C4—H4B	107.8	C17—C16—H16	120.3
O2—C5—C4	106.5 (2)	C15—C16—H16	120.3
O2—C5—H5A	110.4	C16—C17—C18	120.4 (3)
C4—C5—H5A	110.4	C16—C17—H17	119.8
O2—C5—H5B	110.4	C18—C17—H17	119.8
C4—C5—H5B	110.4	C19—C18—C17	119.8 (3)
H5A—C5—H5B	108.6	C19—C18—H18	120.1
N1—C6—C7	120.8 (3)	C17—C18—H18	120.1
N1—C6—H6	119.6	C18—C19—C14	121.3 (3)
C7—C6—H6	119.6	C18—C19—H19	119.3
C12—C7—C8	116.7 (3)	C14—C19—H19	119.3
C6—N1—O1—C1	−179.5 (3)	C9—C10—C11—C12	−0.5 (6)
C13—N2—O2—C5	177.0 (3)	C10—C11—C12—C7	1.3 (5)
N1—O1—C1—C2	−178.3 (2)	C8—C7—C12—C11	−1.5 (5)
O1—C1—C2—C3	−175.9 (2)	C6—C7—C12—C11	179.2 (3)
C1—C2—C3—C4	179.9 (3)	O2—N2—C13—C14	−179.5 (3)
C2—C3—C4—C5	179.5 (3)	N2—C13—C14—C15	−178.9 (3)
N2—O2—C5—C4	172.1 (2)	N2—C13—C14—C19	2.0 (5)
C3—C4—C5—O2	−177.2 (3)	C19—C14—C15—C16	0.6 (5)
O1—N1—C6—C7	−179.8 (3)	C13—C14—C15—C16	−178.5 (3)
N1—C6—C7—C12	−5.7 (5)	C19—C14—C15—Cl2	−179.9 (2)
N1—C6—C7—C8	175.1 (3)	C13—C14—C15—Cl2	1.0 (4)
C12—C7—C8—C9	0.9 (5)	C14—C15—C16—C17	−0.3 (5)
C6—C7—C8—C9	−179.8 (3)	Cl2—C15—C16—C17	−179.9 (3)
C12—C7—C8—Cl1	−178.7 (2)	C15—C16—C17—C18	−0.2 (5)
C6—C7—C8—Cl1	0.6 (4)	C16—C17—C18—C19	0.4 (5)
C7—C8—C9—C10	−0.1 (5)	C17—C18—C19—C14	−0.2 (5)
Cl1—C8—C9—C10	179.4 (3)	C15—C14—C19—C18	−0.4 (5)
C8—C9—C10—C11	−0.1 (5)	C13—C14—C19—C18	178.8 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10···O2i	0.93	2.60	3.527 (4)	177

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C10—H10⋯O2i	0.93	2.60	3.527 (4)	177

Symmetry code: (i) .