2,2′-Dichloro-1,1′-[(pentane-1,5-diyldi­oxy)bis­(nitrilo­methyl­idyne)]dibenzene

Dong, W.-K.; Tong, J.-F.; Wu, J.-C.; Li, Li; Yao, J.

doi:10.1107/S1600536809027433

organic compounds

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Volume 65| Part 8| August 2009| Page o1904

doi:10.1107/S1600536809027433

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2,2′-Dichloro-1,1′-[(pentane-1,5-diyldioxy)bis(nitrilomethylidyne)]dibenzene

Wen-Kui Dong,^a ^* Jun-Feng Tong,^a Jian-Chao Wu,^a Li Li ^a and Jian Yao ^a

^aSchool of Chemical and Biological Engineering, Lanzhou Jiaotong University, Lanzhou 730070, People's Republic of China
^*Correspondence e-mail: dongwk@mail.lzjtu.cn

(Received 9 July 2009; accepted 13 July 2009; online 18 July 2009)

The molecule of the title compound, C₁₉H₂₀Cl₂N₂O₂, which lies across a crystallographic inversion centre, adopts a linear configuration. The dihedral angle between the two halves of the molecule is 5.14 (2)°. In the crystal structure, intermolecular C—H⋯O hydrogen bonds link neighbouring molecules into an infinite zigzag chain supramolecular structure.

Related literature

For background to Schiff base compounds in transition 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_r = 379.27
Monoclinic, P 2₁ /c
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[F² > 2σ(F²)] = 0.045
wR(F²) = 0.116
S = 1.02
3376 reflections
226 parameters
H-atom parameters constrained
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.25 e Å⁻³

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) $[-x+2, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809027433/hg2535sup1.cif

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

checkCIF report

Comment top

Schiff base compounds are one kind of important stereochemical models in transition metal coordination chemistry due to their ease of preparation and structural variations (Granovski et al., 1993) and play an important role in the development of coordination chemistry owing to forming stable complexes with most of the transition metals or nontransition metals, in which many could exhibit intresting properties, including magnetic, optics and catalysis (Ghosh et al., 2006; Ward et al., 2007). In view of these facts and in continuation of our works on the synthesis and structural characterization of Schiff base bisoxime compounds (Dong et al., 2008a), here we report synthesis and crystal structure of the title compound (Fig. 1).

The single-crystal structure of the title compound has a crystallographic inversion centre (symmetry code: -x, -y, -z) and twofold screw axis (symmetry code: -x, 1/2 + y, 1/2 - z), and adopts a linear configuration. This structure is not similar to what was observed in our previously reported series bisoxime compounds containing five-methene bridge, which assume a W-shape configuration (Dong et al., 2008b) and distorted Z configuration (Sun et al., 2009). The dihedral angle between the two halves of the molecule is 5.14 (2)°. Intermolecular C—H···O hydrogen bonds (Table 1, Fig. 2) link the neighbouring molecules into an infinite zigzag chain supramolecular structure.

Related literature top

For background to Schiff base compounds in transition 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 top

2,2'-Dichloro-1,1'-[(pentane-1,5-diyldioxy)bis(nitrilomethylidyne)]dibenzene was synthesized according to an analogous method reported earlier (Dong et al., 2009). To an ethanol solution (4 ml) of o-chlorobenzaldehyde (394.1 mg, 2.80 mmol) was added an ethanol absolute (3 ml) of 1, 5-bis(aminooxy)pentane (187.9 mg, 1.40 mmol). The mixture solution was stirred at 328 K for 8 h. After cooling to room temperature, no precipitate was formed, when the mixture solution was concentrated to about 1 ml under reduced pressure, and cooled to room temperature, the precipitate was filtered, and washed successively with ethanol and n-hexane, respectively. The product was dried under vacuum and purified with recrystallization from ethanol to yield 119.1 mg of the title compound. Yield, 24.7%. m. p. 327–328 K. Anal. Calcd. for C₁₉H₂₀Cl₂N₂O₂: C, 60.17; H, 5.32; N, 7.39. Found: C, 60.10; H, 5.53; N, 7.27.

Colorless needle-like single crystals suitable for X-ray diffraction studies were obtained after one month by slow evaporation from a methanol solution of the title compound.

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecule structure of the title compound with the atom numbering scheme. Displacement ellipsoids for non-hydrogen atoms are drawn at the 30% probability level.
	Fig. 2. Part of zigzag chain supramolecular structure is formed by C—H···O intermolecular interactions with H bonds drawn as dashed lines. H atoms not involved in hydrogen bonding have been omitted for clarity.

2,2'-Dichloro-1,1'-[(pentane-1,5-diyldioxy)bis(nitrilomethylidyne)]dibenzene top

Crystal data top

C₁₉H₂₀Cl₂N₂O₂	F(000) = 792
M_r = 379.27	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0407P)² + 0.181P] where P = (F_o² + 2F_c²)/3
3376 reflections	(Δ/σ)_max = 0.001
226 parameters	Δρ_max = 0.21 e Å⁻³
0 restraints	Δρ_min = −0.25 e Å⁻³

Crystal data top

C₁₉H₂₀Cl₂N₂O₂	V = 1917.7 (3) Å³
M_r = 379.27	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 12.5025 (12) Å	µ = 0.35 mm⁻¹
b = 19.7801 (17) Å	T = 298 K
c = 7.8085 (9) Å	0.45 × 0.30 × 0.28 mm
β = 96.747 (1)°

Data collection top

Bruker SMART CCD area-detector diffractometer	3376 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1631 reflections with I > 2σ(I)
T_min = 0.857, T_max = 0.908	R_int = 0.048
9529 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	0 restraints
wR(F²) = 0.116	H-atom parameters constrained
S = 1.02	Δρ_max = 0.21 e Å⁻³
3376 reflections	Δρ_min = −0.25 e Å⁻³
226 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x+2, y−1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₉H₂₀Cl₂N₂O₂
M_r	379.27
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	12.5025 (12), 19.7801 (17), 7.8085 (9)
β (°)	96.747 (1)
V (Å³)	1917.7 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.35
Crystal size (mm)	0.45 × 0.30 × 0.28

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.857, 0.908
No. of measured, independent and observed [I > 2σ(I)] reflections	9529, 3376, 1631
R_int	0.048
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.116, 1.02
No. of reflections	3376
No. of parameters	226
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.21, −0.25

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10···O2ⁱ	0.93	2.60	3.527 (4)	177.1

Symmetry code: (i) −x+2, y−1/2, −z+1/2.

Acknowledgements

This work was supported by the Foundation of the Education Department of Gansu Province and the `Jing Lan' Talent Engineering Funds of Lanzhou Jiaotong University, which are gratefully acknowledged.

References

Dong, W.-K., He, X.-N., Guan, Y.-H., Xu, L. & Ren, Z.-L. (2008b). Acta Cryst. E64, o1600–o1601. Web of Science CSD CrossRef IUCr Journals Google Scholar
Dong, W. K., Shi, J. Y., Zhong, J. K., Tian, Y. Q. & Duan, J. G. (2008a). Chin. J. Inorg. Chem. 28, 10–14. Google Scholar
Dong, W.-K., Wu, J.-C., Sun, Y.-X., Yao, J. & Tong, J.-F. (2009). Acta Cryst. E65, o1248. Web of Science CSD CrossRef IUCr Journals Google Scholar
Ghosh, R., Rahaman, S. H., Lin, C. N., Lu, T. H. & Ghosh, B. K. (2006). Polyhedron, 25, 3104–3112. Web of Science CSD CrossRef CAS Google Scholar
Granovski, A. D., Nivorozhkin, A. L. & Minkin, V. I. (1993). Coord. Chem. Rev. 126, 1–69. Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Siemens (1996). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA. Google Scholar
Sun, Y.-X., Wu, J.-C., Dong, W.-K., Gong, S. & Tong, J.-F. (2009). Acta Cryst. E65, o1238. Web of Science CSD CrossRef IUCr Journals Google Scholar
Ward, M. D. (2007). Coord. Chem. Rev. 251, 1663–1667. Web of Science CrossRef CAS Google Scholar

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Volume 65| Part 8| August 2009| Page o1904

doi:10.1107/S1600536809027433

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

2,2′-Di­chloro-1,1′-[(pentane-1,5-diyldi­­oxy)bis­­(nitrilo­methyl­­idyne)]di­benzene

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Acknowledgements

References

organic compounds

2,2′-Dichloro-1,1′-[(pentane-1,5-diyldioxy)bis(nitrilomethylidyne)]dibenzene