trans-Dichloridobis[(6-nicotinoyl-2-pyridyl-κN6)(3-pyridyl-κN)methanone]copper(II)

Qiang, H.; Zhang, F.

doi:10.1107/S1600536811017685

metal-organic compounds

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Volume 67| Part 6| June 2011| Page m758

doi:10.1107/S1600536811017685

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trans-Dichloridobis[(6-nicotinoyl-2-pyridyl-κN⁶)(3-pyridyl-κN)methanone]copper(II)

Hong Qiang ^a ^* and Fan Zhang ^a

^aDepartment of Chemistry, Capital Normal University, Beijing 100048, People's Republic of China
^*Correspondence e-mail: qiang-hong@163.com

(Received 6 May 2011; accepted 10 May 2011; online 14 May 2011)

In the title complex, [CuCl₂(C₁₇H₁₁N₃O₂)₂], the Cu^II ion is located on an inversion center. It exhibits a distorted octahedral coordination geometry defined by two chloride anions at trans sites and four 3-pyridyl N atoms at equatorial sites from two (6-nicotinoyl-2-pyridyl)(3-pyridyl)methanone ligands. The (6-nicotinoyl-2-pyridyl)(3-pyridyl)methanone ligand can be viewed as having two pendant 3-pyridyl rings attached to a central pyridyl skeleton via separate carbonyl bridges, acting in a κ²N,N′-chelating mode with its 3-pyridyl N atoms bound to the Cu^II ion. The pendant 3-pyridyl rings make a dihedral angle of 80.76 (5)°. In the crystal, molecules are linked through intermolecular C—H⋯π and C—H⋯O interactions, forming a three-dimentional framework.

Related literature

For transition metal complexes with di-pyrid-2-yl ketone, see: Papaefstathiou & Perlepes (2002 ); Efthymiou et al. (2006 ). For the crystal structure of an analogous Cu^II complex, see: Wan et al. (2008 ). For C—H⋯π interactions, see: Umezawa et al. (1998 ).

Experimental

Crystal data

[CuCl₂(C₁₇H₁₁N₃O₂)₂]
M_r = 713.02
Monoclinic, C 2/c
a = 18.728 (3) Å
b = 11.8971 (18) Å
c = 16.695 (3) Å
β = 121.522 (3)°
V = 3170.9 (8) Å³
Z = 4
Mo Kα radiation
μ = 0.91 mm⁻¹
T = 293 K
0.40 × 0.30 × 0.30 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2007 ) T_min = 0.848, T_max = 1.000
11215 measured reflections
3937 independent reflections
3361 reflections with I > 2σ(I)
R_int = 0.020

Refinement

R[F² > 2σ(F²)] = 0.029
wR(F²) = 0.084
S = 1.04
3937 reflections
215 parameters
H-atom parameters constrained
Δρ_max = 0.25 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C13–C17,N3 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13—H13A⋯O1ⁱ	0.93	2.61	3.418 (2)	146
C2—H2A⋯Cg1ⁱⁱ	0.93	2.73	3.621 (3)	162
Symmetry codes: (i) $[x+{\script{1\over 2}}, y-{\script{1\over 2}}, z]$ ; (ii) $[-x+1, y, -z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2007); cell refinement: APEX2 and SAINT (Bruker, 2007); 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 and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811017685/zq2102sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811017685/zq2102Isup2.hkl

checkCIF report

Comment top

Di-pyridin-2-yl-methanone (di-pyrid-2-yl ketone, DPK), (C₅H₄N)₂CO, is an extraordinarily versatile ligand among the thousands of basic building blocks that have been used in coordination chemistry and materials science (Papaefstathiou & Perlepes, 2002; Efthymiou et al., 2006). Herein, we report the mononuclear Cu^II complex with the oligo-pyridyl ketone ligand (6-nicotinoyl-2-pyridyl)(3-pyridyl)methanone (abbreviated as L), a member of the pyridinylmethanone family.

In the crystal structure of the title complex, the center Cu^II adopts an octahedral coordination geometry with two chlorido depositing in trans to each other, and two 2,6-pyridinediylbis(3-pyridinyl)methanone ligands bound to the ion by four 3-pyridyl N atoms (Fig. 1). The Cu1—N3 and Cu1—Cl1 bond lengths equal 2.0412 (12) Å and 2.3087 (4) Å, respectively, while the Cu-N1 exhibits weak bonding with the Cu-N1 distance of 2.615 (1) Å. The latter Cu—N bonds are remarkably longer than that (about 2.03 Å) in the similar complex Cu(L)₂(BF₄)₂ (Wan et al. 2008). The pendant 3-pyridyl rings exhibit a dihedral angle of 80.76 (5)°. The mononuclear complex units link each other through the intermolecular C2—H2A···π and C13—H13A···O1ⁱⁱ interactions to form a three-dimentional framework, as shown in Fig. 2. For the C—H···π interaction (Umezawa et al. 1998), the C2···Cg1 distance (where Cg1 is the centroid of the ring containing N3ⁱ; i: -x+1, -y, 0.5-z) is 3.621 (3) Å, and the C2—H2A···Cg1 angle is 161.8° . For the C—H···O interaction, the C13···O1ⁱⁱ distance is 3.418 (2) Å, and the C13—H13A···O1ⁱⁱ angle is 146.2° (ii: x+0.5, y-0.5, z).

Related literature top

For transition metal complexes with di-pyrid-2-yl ketone, see: Papaefstathiou & Perlepes (2002); Efthymiou et al. (2006). For the crystal structure of an analogous Cu^II complex, see: Wan et al. (2008). For C—H···π interactions, see: Umezawa et al.(1998).

Experimental top

The (6-nicotinoyl-2-pyridyl)(3-pyridyl)methanone ligand was obtained following the reaction procedure as reported in literature (Wan et al., 2008). Reaction of (6-nicotinoyl-2-pyridyl)(3-pyridyl)methanone (29 mg, 0.1 mmol) with CuCl₂ (7 mg, 0.05 mmol) in acetonitrile formed trans-[Cu(C₁₇H₁₁N₃O₂)₂Cl₂] as a blue solution, which was left stand in air for four days to obtain block-like crystals (yield 13.1mg, 61%).

Computing details top

Data collection: APEX2 (Bruker 2007); cell refinement: APEX2 and SAINT (Bruker 2007); data reduction: SAINT (Bruker 2007); 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) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The atom-numbering scheme of the title complex (symmetry code: (i) -x+1.5, -y+0.5, -z+1.5) with red-dashed lines indicating weak Cu1-N1 bonding. Displacement ellipsoids are drawn at the 50% probability level and H atoms are omitted for clarity.
	Fig. 2. View of the crystal packing of the title compound.

trans-Dichloridobis[(6-nicotinoyl-2-pyridyl-κN⁶)(3-pyridyl- κN)methanone]copper(II) top

Crystal data top

[CuCl₂(C₁₇H₁₁N₃O₂)₂]	Z = 4
M_r = 713.02	F(000) = 1452
Monoclinic, C2/c	D_x = 1.494 Mg m⁻³
Hall symbol: -C 2yc	Mo Kα radiation, λ = 0.71073 Å
a = 18.728 (3) Å	µ = 0.91 mm⁻¹
b = 11.8971 (18) Å	T = 293 K
c = 16.695 (3) Å	Block, blue
β = 121.522 (3)°	0.40 × 0.30 × 0.30 mm
V = 3170.9 (8) Å³

Data collection top

Bruker APEXII CCD area-detector diffractometer	3937 independent reflections
Radiation source: fine-focus sealed tube	3361 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.020
ω scans	θ_max = 28.3°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −24→24
T_min = 0.848, T_max = 1.000	k = −15→15
11215 measured reflections	l = −19→22

Refinement top

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)] = 0.029	H-atom parameters constrained
wR(F²) = 0.084	w = 1/[σ²(F_o²) + (0.0423P)² + 2.1803P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max = 0.001
3937 reflections	Δρ_max = 0.25 e Å⁻³
215 parameters	Δρ_min = −0.21 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.00079 (17)

Crystal data top

[CuCl₂(C₁₇H₁₁N₃O₂)₂]	V = 3170.9 (8) Å³
M_r = 713.02	Z = 4
Monoclinic, C2/c	Mo Kα radiation
a = 18.728 (3) Å	µ = 0.91 mm⁻¹
b = 11.8971 (18) Å	T = 293 K
c = 16.695 (3) Å	0.40 × 0.30 × 0.30 mm
β = 121.522 (3)°

Data collection top

Bruker APEXII CCD area-detector diffractometer	3937 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2007)	3361 reflections with I > 2σ(I)
T_min = 0.848, T_max = 1.000	R_int = 0.020
11215 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.029	0 restraints
wR(F²) = 0.084	H-atom parameters constrained
S = 1.04	Δρ_max = 0.25 e Å⁻³
3937 reflections	Δρ_min = −0.21 e Å⁻³
215 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
Cu1	0.7500	0.2500	0.5000	0.03142 (9)
Cl1	0.69747 (3)	0.11938 (3)	0.38011 (3)	0.03905 (11)
O2	0.77486 (11)	0.74717 (10)	0.35782 (15)	0.0670 (5)
C12	0.73237 (11)	0.67642 (13)	0.36615 (13)	0.0423 (4)
C1	0.45389 (14)	0.2790 (2)	0.33217 (19)	0.0666 (6)
H1A	0.4120	0.2267	0.2971	0.080*
C2	0.43565 (12)	0.39132 (18)	0.32729 (16)	0.0588 (5)
H2A	0.3811	0.4166	0.2878	0.071*
C3	0.49909 (10)	0.46676 (15)	0.38157 (12)	0.0404 (4)
C4	0.57867 (10)	0.42349 (14)	0.44252 (12)	0.0386 (3)
H4A	0.6207	0.4729	0.4830	0.046*
N1	0.59789 (9)	0.31499 (12)	0.44589 (11)	0.0464 (3)
C5	0.53567 (13)	0.24547 (15)	0.39018 (18)	0.0571 (5)
H5A	0.5483	0.1698	0.3905	0.069*
C6	0.47982 (11)	0.58898 (16)	0.37172 (13)	0.0453 (4)
O1	0.41059 (9)	0.62239 (13)	0.35012 (13)	0.0676 (4)
C7	0.54433 (11)	0.67304 (14)	0.38234 (13)	0.0432 (4)
C8	0.53320 (14)	0.78598 (18)	0.39550 (17)	0.0602 (5)
H8A	0.4891	0.8084	0.4023	0.072*
C9	0.58907 (15)	0.86377 (16)	0.39825 (18)	0.0657 (6)
H9A	0.5826	0.9397	0.4062	0.079*
C10	0.65408 (13)	0.82833 (15)	0.38923 (14)	0.0520 (5)
H10A	0.6924	0.8795	0.3908	0.062*
C11	0.66154 (11)	0.71359 (13)	0.37759 (12)	0.0394 (4)
N2	0.60753 (9)	0.63678 (11)	0.37358 (10)	0.0378 (3)
N3	0.76337 (8)	0.36519 (10)	0.41813 (9)	0.0300 (3)
C14	0.74131 (10)	0.47290 (12)	0.41611 (11)	0.0314 (3)
H14A	0.7177	0.4935	0.4510	0.038*
C15	0.75214 (10)	0.55503 (12)	0.36437 (11)	0.0338 (3)
C16	0.78887 (11)	0.52392 (15)	0.31374 (12)	0.0419 (4)
H16A	0.7983	0.5770	0.2794	0.050*
C17	0.81099 (11)	0.41376 (15)	0.31523 (13)	0.0431 (4)
H17A	0.8353	0.3914	0.2815	0.052*
C13	0.79703 (10)	0.33587 (14)	0.36711 (11)	0.0368 (3)
H13A	0.8113	0.2611	0.3667	0.044*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.04854 (17)	0.01975 (13)	0.03224 (15)	−0.00100 (10)	0.02548 (13)	0.00062 (9)
Cl1	0.0554 (2)	0.02824 (18)	0.0347 (2)	−0.00295 (15)	0.02439 (18)	−0.00262 (14)
O2	0.0755 (10)	0.0343 (7)	0.1049 (14)	−0.0040 (6)	0.0566 (10)	0.0174 (7)
C12	0.0487 (9)	0.0296 (7)	0.0459 (9)	−0.0008 (7)	0.0230 (8)	0.0109 (7)
C1	0.0446 (11)	0.0549 (12)	0.0815 (16)	−0.0138 (9)	0.0198 (11)	−0.0136 (11)
C2	0.0344 (9)	0.0595 (12)	0.0661 (13)	0.0007 (8)	0.0149 (9)	−0.0019 (10)
C3	0.0366 (8)	0.0426 (9)	0.0436 (9)	0.0033 (7)	0.0221 (7)	0.0027 (7)
C4	0.0371 (8)	0.0365 (8)	0.0390 (8)	−0.0007 (6)	0.0177 (7)	0.0016 (6)
N1	0.0412 (8)	0.0358 (7)	0.0534 (9)	0.0007 (6)	0.0186 (7)	0.0041 (6)
C5	0.0498 (11)	0.0376 (10)	0.0752 (15)	−0.0054 (8)	0.0266 (11)	−0.0042 (9)
C6	0.0433 (9)	0.0466 (9)	0.0468 (10)	0.0112 (8)	0.0242 (8)	0.0031 (8)
O1	0.0517 (8)	0.0637 (9)	0.0945 (12)	0.0184 (7)	0.0432 (9)	0.0034 (8)
C7	0.0444 (9)	0.0361 (8)	0.0428 (9)	0.0093 (7)	0.0185 (8)	0.0022 (7)
C8	0.0609 (13)	0.0440 (10)	0.0716 (14)	0.0169 (9)	0.0318 (11)	−0.0033 (10)
C9	0.0750 (15)	0.0305 (9)	0.0796 (15)	0.0102 (9)	0.0320 (13)	−0.0070 (9)
C10	0.0630 (12)	0.0273 (8)	0.0548 (11)	−0.0004 (8)	0.0233 (10)	0.0011 (7)
C11	0.0489 (9)	0.0264 (7)	0.0365 (8)	0.0033 (6)	0.0178 (7)	0.0052 (6)
N2	0.0430 (7)	0.0279 (6)	0.0397 (7)	0.0055 (5)	0.0196 (6)	0.0041 (5)
N3	0.0373 (7)	0.0248 (5)	0.0326 (6)	0.0011 (5)	0.0214 (6)	0.0023 (5)
C14	0.0374 (7)	0.0264 (7)	0.0343 (7)	0.0021 (6)	0.0213 (6)	0.0036 (6)
C15	0.0366 (8)	0.0284 (7)	0.0352 (8)	−0.0024 (6)	0.0179 (6)	0.0052 (6)
C16	0.0462 (9)	0.0437 (9)	0.0407 (9)	−0.0072 (7)	0.0262 (8)	0.0073 (7)
C17	0.0491 (10)	0.0495 (9)	0.0438 (9)	−0.0021 (8)	0.0335 (8)	−0.0011 (7)
C13	0.0428 (9)	0.0332 (7)	0.0394 (8)	0.0019 (6)	0.0251 (7)	−0.0011 (6)

Geometric parameters (Å, º) top

Cu1—N3	2.0412 (12)	C7—N2	1.338 (2)
Cu1—N3ⁱ	2.0412 (12)	C7—C8	1.395 (3)
Cu1—Cl1	2.3087 (4)	C8—C9	1.380 (3)
Cu1—Cl1ⁱ	2.3087 (4)	C8—H8A	0.9300
O2—C12	1.215 (2)	C9—C10	1.369 (3)
C12—C15	1.495 (2)	C9—H9A	0.9300
C12—C11	1.502 (3)	C10—C11	1.396 (2)
C1—C2	1.371 (3)	C10—H10A	0.9300
C1—C5	1.376 (3)	C11—N2	1.339 (2)
C1—H1A	0.9300	N3—C14	1.3415 (18)
C2—C3	1.383 (3)	N3—C13	1.3438 (19)
C2—H2A	0.9300	C14—C15	1.3875 (19)
C3—C4	1.391 (2)	C14—H14A	0.9300
C3—C6	1.487 (2)	C15—C16	1.390 (2)
C4—N1	1.333 (2)	C16—C17	1.371 (2)
C4—H4A	0.9300	C16—H16A	0.9300
N1—C5	1.332 (2)	C17—C13	1.383 (2)
C5—H5A	0.9300	C17—H17A	0.9300
C6—O1	1.217 (2)	C13—H13A	0.9300
C6—C7	1.506 (3)

N3—Cu1—N3ⁱ	180.0	C9—C8—C7	118.57 (19)
N3—Cu1—Cl1	90.99 (4)	C9—C8—H8A	120.7
N3ⁱ—Cu1—Cl1	89.01 (4)	C7—C8—H8A	120.7
N3—Cu1—Cl1ⁱ	89.01 (4)	C10—C9—C8	119.50 (18)
N3ⁱ—Cu1—Cl1ⁱ	90.99 (4)	C10—C9—H9A	120.2
Cl1—Cu1—Cl1ⁱ	180.0	C8—C9—H9A	120.2
O2—C12—C15	118.88 (17)	C9—C10—C11	118.42 (19)
O2—C12—C11	119.02 (16)	C9—C10—H10A	120.8
C15—C12—C11	122.10 (14)	C11—C10—H10A	120.8
C2—C1—C5	118.40 (19)	N2—C11—C10	123.12 (17)
C2—C1—H1A	120.8	N2—C11—C12	119.14 (14)
C5—C1—H1A	120.8	C10—C11—C12	117.71 (16)
C1—C2—C3	119.45 (18)	C7—N2—C11	117.58 (14)
C1—C2—H2A	120.3	C14—N3—C13	118.19 (13)
C3—C2—H2A	120.3	C14—N3—Cu1	120.94 (10)
C2—C3—C4	117.64 (17)	C13—N3—Cu1	120.84 (10)
C2—C3—C6	119.12 (16)	N3—C14—C15	123.02 (14)
C4—C3—C6	123.23 (16)	N3—C14—H14A	118.5
N1—C4—C3	123.46 (16)	C15—C14—H14A	118.5
N1—C4—H4A	118.3	C14—C15—C16	118.09 (14)
C3—C4—H4A	118.3	C14—C15—C12	123.33 (14)
C5—N1—C4	116.97 (16)	C16—C15—C12	118.41 (14)
N1—C5—C1	123.86 (18)	C17—C16—C15	118.97 (14)
N1—C5—H5A	118.1	C17—C16—H16A	120.5
C1—C5—H5A	118.1	C15—C16—H16A	120.5
O1—C6—C3	120.78 (18)	C16—C17—C13	119.84 (15)
O1—C6—C7	118.89 (17)	C16—C17—H17A	120.1
C3—C6—C7	120.22 (15)	C13—C17—H17A	120.1
N2—C7—C8	122.80 (18)	N3—C13—C17	121.86 (15)
N2—C7—C6	118.31 (15)	N3—C13—H13A	119.1
C8—C7—C6	118.79 (17)	C17—C13—H13A	119.1

C5—C1—C2—C3	−1.2 (4)	O2—C12—C11—C10	−7.4 (3)
C1—C2—C3—C4	−2.9 (3)	C15—C12—C11—C10	172.79 (16)
C1—C2—C3—C6	176.4 (2)	C8—C7—N2—C11	−0.2 (3)
C2—C3—C4—N1	5.2 (3)	C6—C7—N2—C11	176.08 (15)
C6—C3—C4—N1	−174.07 (17)	C10—C11—N2—C7	−0.8 (3)
C3—C4—N1—C5	−3.0 (3)	C12—C11—N2—C7	−178.81 (15)
C4—N1—C5—C1	−1.6 (3)	Cl1—Cu1—N3—C14	136.92 (12)
C2—C1—C5—N1	3.7 (4)	Cl1ⁱ—Cu1—N3—C14	−43.08 (12)
C2—C3—C6—O1	30.2 (3)	Cl1—Cu1—N3—C13	−45.23 (12)
C4—C3—C6—O1	−150.5 (2)	Cl1ⁱ—Cu1—N3—C13	134.77 (12)
C2—C3—C6—C7	−145.85 (19)	C13—N3—C14—C15	−0.4 (2)
C4—C3—C6—C7	33.5 (3)	Cu1—N3—C14—C15	177.50 (11)
O1—C6—C7—N2	−157.20 (19)	N3—C14—C15—C16	−1.1 (2)
C3—C6—C7—N2	18.9 (3)	N3—C14—C15—C12	−176.31 (15)
O1—C6—C7—C8	19.2 (3)	O2—C12—C15—C14	146.67 (19)
C3—C6—C7—C8	−164.64 (18)	C11—C12—C15—C14	−33.5 (2)
N2—C7—C8—C9	1.0 (3)	O2—C12—C15—C16	−28.5 (3)
C6—C7—C8—C9	−175.3 (2)	C11—C12—C15—C16	151.27 (16)
C7—C8—C9—C10	−0.8 (4)	C14—C15—C16—C17	1.5 (2)
C8—C9—C10—C11	−0.1 (3)	C12—C15—C16—C17	176.90 (16)
C9—C10—C11—N2	0.9 (3)	C15—C16—C17—C13	−0.4 (3)
C9—C10—C11—C12	178.98 (19)	C14—N3—C13—C17	1.6 (2)
O2—C12—C11—N2	170.73 (18)	Cu1—N3—C13—C17	−176.35 (13)
C15—C12—C11—N2	−9.1 (2)	C16—C17—C13—N3	−1.2 (3)

Symmetry code: (i) −x+3/2, −y+1/2, −z+1.

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C13–C17,N3 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13A···O1ⁱⁱ	0.93	2.61	3.418 (2)	146
C2—H2A···Cg1ⁱⁱⁱ	0.93	2.73	3.621 (3)	162

Symmetry codes: (ii) x+1/2, y−1/2, z; (iii) −x+1, y, −z+1/2.

Experimental details

Crystal data
Chemical formula	[CuCl₂(C₁₇H₁₁N₃O₂)₂]
M_r	713.02
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	293
a, b, c (Å)	18.728 (3), 11.8971 (18), 16.695 (3)
β (°)	121.522 (3)
V (Å³)	3170.9 (8)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.91
Crystal size (mm)	0.40 × 0.30 × 0.30

Data collection
Diffractometer	Bruker APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2007)
T_min, T_max	0.848, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	11215, 3937, 3361
R_int	0.020
(sin θ/λ)_max (Å⁻¹)	0.668

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.029, 0.084, 1.04
No. of reflections	3937
No. of parameters	215
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.25, −0.21

Computer programs: APEX2 (Bruker 2007), APEX2 and SAINT (Bruker 2007), SAINT (Bruker 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C13–C17,N3 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13A···O1ⁱ	0.93	2.61	3.418 (2)	146
C2—H2A···Cg1ⁱⁱ	0.93	2.73	3.621 (3)	162

Symmetry codes: (i) x+1/2, y−1/2, z; (ii) −x+1, y, −z+1/2.

Acknowledgements

The authors are grateful for financial support from the Science and Technology program, Beijing Municipal Education Commission.

References

Bruker (2007). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Efthymiou, C. G., Raptopoulou, C. P., Terzis, A., Boca, R., Korabic, M., Mrozinski, J., Perlepes, S. P. & Bakalbassis, E. G. (2006). Eur. J. Inorg. Chem. 11, 2236–2252. CrossRef Google Scholar
Papaefstathiou, G. S. & Perlepes, S. P. (2002). Comments Inorg. Chem. 23, 249–274. Web of Science CrossRef CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Umezawa, Y., Tsuboyama, S., Honda, K., Uzawa, J. & Nishio, M. (1998). Bull. Chem. Soc. Jpn, 71, 1202–1213. Web of Science CrossRef Google Scholar
Wan, C. Q., Chen, X. D. & Mak, T. C. W. (2008). CrystEngComm, 10, 475–478. Web of Science CSD CrossRef CAS Google Scholar

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Volume 67| Part 6| June 2011| Page m758

doi:10.1107/S1600536811017685

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