catena-Poly[copper(II)-{μ3-4,4′-dibromo-2,2′-[butane-1,4-diylbis(nitrilo­methanyl­yl­idene)]diphenolato-κ4N,O:N′,O′:O′}]

Kargar, H.; Kia, R.

doi:10.1107/S1600536811009949

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 4| April 2011| Pages m499-m500

doi:10.1107/S1600536811009949

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catena-Poly[copper(II)-{μ₃-4,4′-dibromo-2,2′-[butane-1,4-diylbis(nitrilomethanylylidene)]diphenolato-κ⁴N,O:N′,O′:O′}]

Hadi Kargar ^a ^* and Reza Kia ^b

^aChemistry Department, Payame Noor University, Tehran 19395-4697, I. R. of Iran, and ^bX-ray Crystallography Laboratory, Plasma Physics Research Center, Science and Research Branch, Islamic Azad University, Tehran, Iran
^*Correspondence e-mail: hkargar@pnu.ac.ir

(Received 7 March 2011; accepted 16 March 2011; online 26 March 2011)

The asymmetric unit of the title coordination polymer, [Cu(C₁₈H₁₆Br₂N₂O₂)]_n, consists of a Schiff base complex in which a crystallographic twofold rotation axis bisects the central C—C bonds of the n-butyl spacers of the designated Schiff base ligands, making symmetry-related dimer units, which are twisted around Cu^II atoms in a bis-bidentate coordination mode. In the crystal, these dimeric units are connected through Cu—O bonds, forming one-dimensional coordination polymers, which propagate along [001]. The Cu^II atom adopts a square-based pyramidal coordination geometry, being coordinated by two N and two O atoms of symmetry-related ligands and by a third O atom of a neighboring complex. Furthermore, intermolecular π–π interactions [centroid–centroid distance = 3.786 (2) Å] and C—H⋯O interactions stabilize the crystal packing.

Related literature

For van der Waals radii, see: Bondi (1964 ). For background to coordination polymers, see: Kido & Okamoto (2002 ); Li et al. (2006 ); Eddaoudi et al. (2001 ); Dietzel et al. (2005 ). For background to bis-bidentate Schiff base complexes, see: Hannon et al. (1999 ); Lavalette et al. (2003 ). For the synthesis and structural variations of Schiff base complexes see: Granovski et al. (1993 ); Elmali et al. (2000 ). For the crystal structure of the chloro derivative, see: Kargar & Kia (2011 ).

Experimental

Crystal data

[Cu(C₁₈H₁₆Br₂N₂O₂)]
M_r = 515.69
Monoclinic, C 2/c
a = 24.0964 (9) Å
b = 10.5885 (3) Å
c = 15.3528 (5) Å
β = 117.354 (3)°
V = 3479.2 (2) Å³
Z = 8
Mo Kα radiation
μ = 5.86 mm⁻¹
T = 100 K
0.41 × 0.32 × 0.17 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ) T_min = 0.197, T_max = 0.439
36229 measured reflections
6017 independent reflections
4887 reflections with I > 2σ(I)
R_int = 0.037

Refinement

R[F² > 2σ(F²)] = 0.049
wR(F²) = 0.139
S = 1.19
6017 reflections
226 parameters
H-atom parameters constrained
Δρ_max = 2.19 e Å⁻³
Δρ_min = −0.73 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C9—H9B⋯O2	0.97	2.28	2.973 (5)	128

Data collection: APEX2 (Bruker, 2007 ); cell refinement: 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 global, I. DOI: 10.1107/S1600536811009949/su2263sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811009949/su2263Isup2.hkl

checkCIF report

Comment top

The design and construction of metal-organic coordination polymers (MOCPs) have attracted considerable attention, not only for their novel topologies but also for their potential in the area of magnetic applications and functional materials (Kido & Okamoto, 2002; Li et al., 2006; Eddaoudi et al., 2001; Dietzel et al., 2005). One of the key strategies in the construction of metal-organic coordination polymers is to select suitable bi- or multi-dentate bridging ligands. Among these, bis-bidentate NN- or NO-donor Schiff base ligands with aliphatic and aromatic spacers (Hannon et al., 1999; Lavalette et al., 2003) have attracted much attention because of the flexibility in their coordination modes and the resulting intermolecular interactions. The long chain aliphatic spacers or rigid aromatic spacers with large bite angles in these ligands favour the bis-bidentate coordination mode and allow the ligands to accomodate metal centers in one unit of the ligand. On the other hand, Schiff bases are one of the most prevalent ligands in coordination chemistry and their complexes are some of the most important stereochemical models in transition metal-organic chemistry, with their ease of preparation and structural variations (Granovski et al., 1993; Elmali et al., 2000).

The crystal structure of the chloro derivative, Poly[N,N'-Bis(5-chlorosalicylidene)-1,4-butanediaminato copper(II)], has been descibed in the previous paper (Kargar & Kia, 2011).

The molecular structure of the title complex (Fig. 1) consists of symmetry-related dimers in which the Schiff base ligands are twisted around Cu^II centers in a bis-bidentate coordinⁿation mode, having a crystallographic twofold rotation axis which passes through the central C—C bonds of the n-butyl spacers [C9—C9Aⁱ and C18—C18Aⁱ; symmetry code: (i) -x + 1, y, -z + 1/2].

In the crystal the dimer units are connected through Cu—O bonds, forming one-diensional coordination polymer running along the c axis (Fig. 2), in which the Cu^II atom adopts a square-based pyramidal coordination geometry. The Cu^II atoms are supported by the two nitrogen and oxygen atoms of the symmetry-related ligands and a third oxygen atom of neighboring complexes. The lengths of the intermolecular Cu1—O1ⁱ bonds [2.394 (3) Å Å; symetry code (i) -x, -y + 1, -z] is significantly shorter than the sum of the van der Waals (vdW) radii of these atoms [Cu, 1.43Å and O, 1.52 Å; Bondi, 1964]. There are different non-bonded internuclear Cu···Cu distances. The longer one is separated by the butyl spacers [4.718 Å], and the shorter one is in the centrosymmetric Cu₂O₂ rectangular unit [3.314 Å]. Furthermore, intermolecular π-π interactions stabilize the crystal packings with centroid to centroid distances of 3.786 (2)Å [Cg1 and Cg2 are the centroids of the rings (C1–C6) and (C10–C15)]. There are also C—H···O interactions present (Table 1).

Related literature top

For van der Waals radii, see: Bondi (1964). For background to coordination polymers, see: Kido & Okamoto (2002); Li et al. (2006); Eddaoudi et al. (2001); Dietzel et al. (2005). For background to bis-bidentate Schiff base complexes, see: Hannon et al. (1999); Lavalette et al. (2003). For the synthesis and structural variations of Schiff base complexes see: Granovski et al. (1993); Elmali et al. (2000). For the crystal structure of the chloro derivative, see: Kargar & Kia (2011).

Experimental top

The title complex was synthesized by the template method of mixing an ethanolic solution (50 ml) of 5-bromosalicylaldeyde (4 mmol), 1,4-butanediamine (2 mmol), and CuCl₂.4H₂O (2.1 mmol). After stirring at reflux conditions for 2 h, the solution was filtered and the resulting green solid was crystallized from ethanol, giving single crystals suitable for X-ray diffraction.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: 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 molecular structure of the title complex, showing 40% probability displacement ellipsoids and the atomic numbering [H-atoms have been omitted for clarity; symmetry code for A suffix: -x + 1, -y, -z + 1].
	Fig. 2. The crystal packing, viewed down the b-axis, of the title complex, showing the one-dimensional coordination chain propagating along [001] (H-atoms have been omitted for clarity).

catena-Poly[copper(II)-{µ₃-4,4'-dibromo-2,2'-[butane-1,4- diylbis(nitrilomethanylylidene)]diphenolato- κ⁴N,O:N',O':O'}] top

Crystal data top

[Cu(C₁₈H₁₆Br₂N₂O₂)]	F(000) = 2024
M_r = 515.69	D_x = 1.969 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 9961 reflections
a = 24.0964 (9) Å	θ = 2.4–34.8°
b = 10.5885 (3) Å	µ = 5.86 mm⁻¹
c = 15.3528 (5) Å	T = 100 K
β = 117.354 (3)°	Block, green
V = 3479.2 (2) Å³	0.41 × 0.32 × 0.17 mm
Z = 8

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	6017 independent reflections
Radiation source: fine-focus sealed tube	4887 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.037
ϕ and ω scans	θ_max = 32.0°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −35→35
T_min = 0.197, T_max = 0.439	k = −15→15
36229 measured reflections	l = −22→22

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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.139	H-atom parameters constrained
S = 1.19	w = 1/[σ²(F_o²) + (0.0486P)² + 32.1161P] where P = (F_o² + 2F_c²)/3
6017 reflections	(Δ/σ)_max = 0.001
226 parameters	Δρ_max = 2.19 e Å⁻³
0 restraints	Δρ_min = −0.73 e Å⁻³

Crystal data top

[Cu(C₁₈H₁₆Br₂N₂O₂)]	V = 3479.2 (2) Å³
M_r = 515.69	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 24.0964 (9) Å	µ = 5.86 mm⁻¹
b = 10.5885 (3) Å	T = 100 K
c = 15.3528 (5) Å	0.41 × 0.32 × 0.17 mm
β = 117.354 (3)°

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	6017 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	4887 reflections with I > 2σ(I)
T_min = 0.197, T_max = 0.439	R_int = 0.037
36229 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.049	0 restraints
wR(F²) = 0.139	H-atom parameters constrained
S = 1.19	w = 1/[σ²(F_o²) + (0.0486P)² + 32.1161P] where P = (F_o² + 2F_c²)/3
6017 reflections	Δρ_max = 2.19 e Å⁻³
226 parameters	Δρ_min = −0.73 e Å⁻³

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
Cu1	0.47745 (2)	−0.03938 (5)	0.38413 (4)	0.01976 (11)
Br1	0.819293 (19)	0.00198 (4)	0.58443 (3)	0.02766 (11)
Br2	0.134787 (18)	0.00911 (4)	0.11824 (3)	0.02394 (10)
O1	0.54761 (13)	0.0506 (3)	0.4822 (2)	0.0236 (6)
O2	0.40617 (13)	−0.1341 (3)	0.2998 (2)	0.0252 (6)
N1	0.53131 (15)	−0.1956 (3)	0.4080 (2)	0.0198 (6)
N2	0.43372 (16)	0.1252 (3)	0.3280 (3)	0.0217 (6)
C1	0.60593 (18)	0.0376 (4)	0.4980 (3)	0.0218 (7)
C2	0.64637 (19)	0.1423 (4)	0.5324 (3)	0.0249 (8)
H2A	0.6310	0.2195	0.5405	0.030*
C3	0.70866 (19)	0.1318 (4)	0.5542 (3)	0.0247 (8)
H3A	0.7347	0.2021	0.5755	0.030*
C4	0.73222 (18)	0.0156 (4)	0.5442 (3)	0.0213 (7)
C5	0.69348 (17)	−0.0878 (4)	0.5073 (3)	0.0209 (7)
H5A	0.7094	−0.1640	0.4987	0.025*
C6	0.62944 (17)	−0.0775 (4)	0.4828 (3)	0.0194 (7)
C7	0.59134 (18)	−0.1902 (4)	0.4466 (3)	0.0209 (7)
H7A	0.6123	−0.2657	0.4517	0.025*
C8	0.50307 (18)	−0.3230 (4)	0.3790 (3)	0.0214 (7)
H8A	0.4702	−0.3323	0.3984	0.026*
H8B	0.5347	−0.3863	0.4138	0.026*
C9	0.47575 (17)	−0.3465 (4)	0.2686 (3)	0.0208 (7)
H9A	0.4544	−0.4273	0.2533	0.025*
H9B	0.4449	−0.2817	0.2341	0.025*
C10	0.34829 (17)	−0.0968 (4)	0.2555 (3)	0.0204 (7)
C11	0.30077 (18)	−0.1890 (4)	0.2123 (3)	0.0223 (7)
H11A	0.3120	−0.2728	0.2115	0.027*
C12	0.23841 (18)	−0.1575 (4)	0.1715 (3)	0.0224 (7)
H12A	0.2080	−0.2199	0.1450	0.027*
C13	0.22092 (17)	−0.0308 (4)	0.1703 (3)	0.0194 (7)
C14	0.26555 (18)	0.0625 (4)	0.2037 (3)	0.0218 (7)
H14A	0.2534	0.1467	0.1980	0.026*
C15	0.32968 (18)	0.0317 (4)	0.2466 (3)	0.0209 (7)
C16	0.37388 (19)	0.1347 (4)	0.2777 (3)	0.0225 (7)
H16A	0.3576	0.2157	0.2597	0.027*
C17	0.47047 (19)	0.2436 (4)	0.3495 (3)	0.0229 (7)
H17A	0.4937	0.2543	0.4200	0.028*
H17B	0.4421	0.3145	0.3233	0.028*
C18	0.51627 (19)	0.2440 (4)	0.3057 (3)	0.0243 (8)
H18A	0.5427	0.3181	0.3289	0.029*
H18B	0.5429	0.1701	0.3289	0.029*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.01465 (19)	0.0223 (2)	0.0209 (2)	0.00107 (16)	0.00695 (16)	−0.00268 (18)
Br1	0.01623 (17)	0.0374 (2)	0.0292 (2)	−0.00192 (15)	0.01023 (15)	−0.00306 (17)
Br2	0.01591 (17)	0.0263 (2)	0.0279 (2)	0.00093 (13)	0.00856 (15)	0.00019 (15)
O1	0.0168 (12)	0.0281 (15)	0.0256 (14)	−0.0010 (11)	0.0096 (11)	−0.0052 (12)
O2	0.0177 (12)	0.0233 (14)	0.0292 (15)	0.0028 (10)	0.0062 (11)	−0.0047 (12)
N1	0.0179 (14)	0.0220 (15)	0.0194 (14)	0.0005 (11)	0.0086 (12)	0.0001 (12)
N2	0.0222 (15)	0.0200 (15)	0.0246 (16)	−0.0012 (12)	0.0123 (13)	−0.0036 (13)
C1	0.0171 (15)	0.0266 (19)	0.0196 (16)	−0.0004 (14)	0.0066 (13)	−0.0041 (15)
C2	0.0224 (17)	0.0256 (19)	0.0271 (19)	−0.0002 (15)	0.0117 (16)	−0.0049 (16)
C3	0.0213 (17)	0.0268 (19)	0.0262 (19)	−0.0051 (14)	0.0111 (15)	−0.0053 (16)
C4	0.0159 (15)	0.031 (2)	0.0174 (16)	−0.0006 (14)	0.0083 (13)	−0.0012 (14)
C5	0.0178 (15)	0.0236 (18)	0.0198 (16)	0.0000 (13)	0.0075 (13)	−0.0022 (14)
C6	0.0174 (15)	0.0227 (17)	0.0169 (15)	0.0002 (13)	0.0068 (13)	−0.0002 (13)
C7	0.0199 (16)	0.0220 (17)	0.0196 (16)	0.0022 (13)	0.0080 (14)	−0.0004 (14)
C8	0.0186 (16)	0.0206 (17)	0.0245 (18)	−0.0019 (13)	0.0095 (14)	0.0003 (14)
C9	0.0165 (15)	0.0222 (17)	0.0234 (17)	−0.0019 (13)	0.0089 (14)	−0.0014 (14)
C10	0.0187 (16)	0.0234 (18)	0.0183 (16)	0.0015 (13)	0.0078 (13)	−0.0005 (14)
C11	0.0186 (16)	0.0224 (18)	0.0223 (18)	0.0013 (13)	0.0062 (14)	−0.0005 (14)
C12	0.0184 (16)	0.0235 (18)	0.0222 (17)	0.0007 (13)	0.0067 (14)	0.0004 (15)
C13	0.0141 (14)	0.0234 (17)	0.0177 (16)	0.0025 (12)	0.0047 (12)	0.0018 (13)
C14	0.0179 (16)	0.0194 (17)	0.0268 (18)	0.0008 (13)	0.0091 (14)	0.0011 (14)
C15	0.0196 (16)	0.0221 (17)	0.0188 (16)	0.0018 (13)	0.0070 (13)	−0.0004 (14)
C16	0.0219 (17)	0.0210 (17)	0.0254 (18)	0.0002 (14)	0.0115 (15)	−0.0023 (15)
C17	0.0221 (17)	0.0208 (18)	0.0286 (19)	−0.0033 (14)	0.0140 (15)	−0.0034 (15)
C18	0.0213 (17)	0.0277 (19)	0.0270 (19)	−0.0019 (14)	0.0138 (15)	−0.0010 (15)

Geometric parameters (Å, º) top

Cu1—O2	1.894 (3)	C7—H7A	0.9300
Cu1—O1	1.922 (3)	C8—C9	1.530 (6)
Cu1—N2	2.014 (4)	C8—H8A	0.9700
Cu1—N1	2.029 (3)	C8—H8B	0.9700
Cu1—O1ⁱ	2.393 (3)	C9—C9ⁱⁱ	1.519 (7)
Br1—C4	1.901 (4)	C9—H9A	0.9700
Br2—C13	1.898 (4)	C9—H9B	0.9700
O1—C1	1.319 (5)	C10—C11	1.416 (5)
O1—Cu1ⁱ	2.393 (3)	C10—C15	1.420 (6)
O2—C10	1.301 (5)	C11—C12	1.377 (5)
N1—C7	1.288 (5)	C11—H11A	0.9300
N1—C8	1.484 (5)	C12—C13	1.404 (6)
N2—C16	1.289 (5)	C12—H12A	0.9300
N2—C17	1.481 (5)	C13—C14	1.374 (5)
C1—C6	1.408 (6)	C14—C15	1.412 (5)
C1—C2	1.409 (6)	C14—H14A	0.9300
C2—C3	1.384 (6)	C15—C16	1.444 (6)
C2—H2A	0.9300	C16—H16A	0.9300
C3—C4	1.393 (6)	C17—C18	1.534 (5)
C3—H3A	0.9300	C17—H17A	0.9700
C4—C5	1.380 (6)	C17—H17B	0.9700
C5—C6	1.414 (5)	C18—C18ⁱⁱ	1.519 (8)
C5—H5A	0.9300	C18—H18A	0.9700
C6—C7	1.451 (6)	C18—H18B	0.9700

O2—Cu1—O1	173.11 (14)	C9—C8—H8A	109.1
O2—Cu1—N2	91.94 (13)	N1—C8—H8B	109.1
O1—Cu1—N2	90.31 (14)	C9—C8—H8B	109.1
O2—Cu1—N1	89.76 (13)	H8A—C8—H8B	107.8
O1—Cu1—N1	90.18 (13)	C9ⁱⁱ—C9—C8	113.8 (4)
N2—Cu1—N1	161.46 (14)	C9ⁱⁱ—C9—H9A	108.8
O2—Cu1—O1ⁱ	93.04 (12)	C8—C9—H9A	108.8
O1—Cu1—O1ⁱ	80.22 (12)	C9ⁱⁱ—C9—H9B	108.8
N2—Cu1—O1ⁱ	96.98 (12)	C8—C9—H9B	108.8
N1—Cu1—O1ⁱ	101.37 (12)	H9A—C9—H9B	107.7
C1—O1—Cu1	124.9 (3)	O2—C10—C11	118.6 (4)
C1—O1—Cu1ⁱ	120.3 (3)	O2—C10—C15	123.8 (4)
Cu1—O1—Cu1ⁱ	99.78 (12)	C11—C10—C15	117.6 (3)
C10—O2—Cu1	127.9 (3)	C12—C11—C10	121.7 (4)
C7—N1—C8	116.2 (3)	C12—C11—H11A	119.2
C7—N1—Cu1	122.4 (3)	C10—C11—H11A	119.2
C8—N1—Cu1	121.3 (2)	C11—C12—C13	119.7 (4)
C16—N2—C17	117.2 (4)	C11—C12—H12A	120.2
C16—N2—Cu1	123.0 (3)	C13—C12—H12A	120.2
C17—N2—Cu1	119.7 (3)	C14—C13—C12	120.2 (3)
O1—C1—C6	122.4 (4)	C14—C13—Br2	120.9 (3)
O1—C1—C2	118.8 (4)	C12—C13—Br2	118.8 (3)
C6—C1—C2	118.8 (4)	C13—C14—C15	120.6 (4)
C3—C2—C1	121.0 (4)	C13—C14—H14A	119.7
C3—C2—H2A	119.5	C15—C14—H14A	119.7
C1—C2—H2A	119.5	C14—C15—C10	119.7 (4)
C2—C3—C4	119.7 (4)	C14—C15—C16	117.6 (4)
C2—C3—H3A	120.2	C10—C15—C16	122.7 (3)
C4—C3—H3A	120.2	N2—C16—C15	126.2 (4)
C5—C4—C3	120.9 (4)	N2—C16—H16A	116.9
C5—C4—Br1	120.7 (3)	C15—C16—H16A	116.9
C3—C4—Br1	118.4 (3)	N2—C17—C18	112.4 (3)
C4—C5—C6	119.9 (4)	N2—C17—H17A	109.1
C4—C5—H5A	120.1	C18—C17—H17A	109.1
C6—C5—H5A	120.1	N2—C17—H17B	109.1
C1—C6—C5	119.7 (4)	C18—C17—H17B	109.1
C1—C6—C7	122.9 (3)	H17A—C17—H17B	107.9
C5—C6—C7	117.4 (4)	C18ⁱⁱ—C18—C17	113.0 (4)
N1—C7—C6	126.3 (4)	C18ⁱⁱ—C18—H18A	109.0
N1—C7—H7A	116.8	C17—C18—H18A	109.0
C6—C7—H7A	116.8	C18ⁱⁱ—C18—H18B	109.0
N1—C8—C9	112.6 (3)	C17—C18—H18B	109.0
N1—C8—H8A	109.1	H18A—C18—H18B	107.8

N2—Cu1—O1—C1	−124.9 (3)	O1—C1—C6—C5	−175.7 (4)
N1—Cu1—O1—C1	36.6 (3)	C2—C1—C6—C5	3.5 (6)
O1ⁱ—Cu1—O1—C1	138.1 (4)	O1—C1—C6—C7	1.4 (6)
N2—Cu1—O1—Cu1ⁱ	97.03 (13)	C2—C1—C6—C7	−179.3 (4)
N1—Cu1—O1—Cu1ⁱ	−101.51 (13)	C4—C5—C6—C1	−1.3 (6)
O1ⁱ—Cu1—O1—Cu1ⁱ	0.0	C4—C5—C6—C7	−178.6 (4)
N2—Cu1—O2—C10	−21.9 (4)	C8—N1—C7—C6	−178.3 (4)
N1—Cu1—O2—C10	176.6 (4)	Cu1—N1—C7—C6	3.4 (6)
O1ⁱ—Cu1—O2—C10	75.2 (4)	C1—C6—C7—N1	13.1 (6)
O2—Cu1—N1—C7	164.8 (3)	C5—C6—C7—N1	−169.7 (4)
O1—Cu1—N1—C7	−22.1 (3)	C7—N1—C8—C9	−101.6 (4)
N2—Cu1—N1—C7	69.4 (6)	Cu1—N1—C8—C9	76.7 (4)
O1ⁱ—Cu1—N1—C7	−102.2 (3)	N1—C8—C9—C9ⁱⁱ	64.2 (3)
O2—Cu1—N1—C8	−13.5 (3)	Cu1—O2—C10—C11	−167.0 (3)
O1—Cu1—N1—C8	159.6 (3)	Cu1—O2—C10—C15	13.7 (6)
N2—Cu1—N1—C8	−108.9 (5)	O2—C10—C11—C12	174.4 (4)
O1ⁱ—Cu1—N1—C8	79.6 (3)	C15—C10—C11—C12	−6.3 (6)
O2—Cu1—N2—C16	17.4 (3)	C10—C11—C12—C13	1.5 (6)
O1—Cu1—N2—C16	−156.1 (3)	C11—C12—C13—C14	4.2 (6)
N1—Cu1—N2—C16	112.4 (5)	C11—C12—C13—Br2	−177.6 (3)
O1ⁱ—Cu1—N2—C16	−75.9 (3)	C12—C13—C14—C15	−4.9 (6)
O2—Cu1—N2—C17	−166.6 (3)	Br2—C13—C14—C15	177.0 (3)
O1—Cu1—N2—C17	19.9 (3)	C13—C14—C15—C10	−0.1 (6)
N1—Cu1—N2—C17	−71.6 (5)	C13—C14—C15—C16	178.4 (4)
O1ⁱ—Cu1—N2—C17	100.1 (3)	O2—C10—C15—C14	−175.2 (4)
Cu1—O1—C1—C6	−31.8 (6)	C11—C10—C15—C14	5.6 (6)
Cu1ⁱ—O1—C1—C6	98.5 (4)	O2—C10—C15—C16	6.4 (6)
Cu1—O1—C1—C2	148.9 (3)	C11—C10—C15—C16	−172.8 (4)
Cu1ⁱ—O1—C1—C2	−80.7 (4)	C17—N2—C16—C15	178.4 (4)
O1—C1—C2—C3	177.1 (4)	Cu1—N2—C16—C15	−5.6 (6)
C6—C1—C2—C3	−2.2 (6)	C14—C15—C16—N2	171.5 (4)
C1—C2—C3—C4	−1.4 (7)	C10—C15—C16—N2	−10.1 (7)
C2—C3—C4—C5	3.8 (6)	C16—N2—C17—C18	−118.7 (4)
C2—C3—C4—Br1	−175.2 (3)	Cu1—N2—C17—C18	65.1 (4)
C3—C4—C5—C6	−2.5 (6)	N2—C17—C18—C18ⁱⁱ	65.9 (3)
Br1—C4—C5—C6	176.6 (3)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9B···O2	0.97	2.28	2.973 (5)	128

Experimental details

Crystal data
Chemical formula	[Cu(C₁₈H₁₆Br₂N₂O₂)]
M_r	515.69
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	100
a, b, c (Å)	24.0964 (9), 10.5885 (3), 15.3528 (5)
β (°)	117.354 (3)
V (Å³)	3479.2 (2)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	5.86
Crystal size (mm)	0.41 × 0.32 × 0.17

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.197, 0.439
No. of measured, independent and observed [I > 2σ(I)] reflections	36229, 6017, 4887
R_int	0.037
(sin θ/λ)_max (Å⁻¹)	0.746

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.049, 0.139, 1.19
No. of reflections	6017
No. of parameters	226
H-atom treatment	H-atom parameters constrained
	w = 1/[σ²(F_o²) + (0.0486P)² + 32.1161P] where P = (F_o² + 2F_c²)/3
Δρ_max, Δρ_min (e Å⁻³)	2.19, −0.73

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9B···O2	0.97	2.28	2.973 (5)	128

Acknowledgements

HK thans PNU for support of this work. RK thanks the Science and Research Branch, Islamic Azad University.

References

Bondi, A. (1964). J. Phys. Chem. 68, 441–451. CrossRef CAS Web of Science Google Scholar
Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Dietzel, P. D. C., Morita, Y., Blom, R. & Fjellvag, H. (2005). Angew. Chem. Int. Ed. 44, 1483–1492. Web of Science CSD CrossRef Google Scholar
Eddaoudi, M., Moler, D., Li, H., Reineke, T. M., O'Keeffe, M. & Yaghi, O. M. (2001). Acc. Chem. Res. 34, 319–330. Web of Science CrossRef PubMed CAS Google Scholar
Elmali, A., Zeyrek, C. T., Elerman, Y. & Svoboda, I. (2000). Acta Cryst. C56, 1302–1304. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Granovski, A. D., Nivorozhkin, A. L. & Minkin, V. I. (1993). Coord. Chem. Rev. 126, 1–69. Google Scholar
Hannon, M. J., Painting, L. C. & Alcock, N. W. (1999). Chem. Commun. pp. 2023–2024. Web of Science CSD CrossRef Google Scholar
Kargar, H. & Kia, R. (2011). Acta Cryst. E67, m497–m498. Web of Science CSD CrossRef IUCr Journals Google Scholar
Kido, J. & Okamoto, Y. (2002). Chem. Rev. 102, 2357–2368. Web of Science CrossRef PubMed CAS Google Scholar
Lavalette, A., Tuna, F., Clarkson, G., Alcock, N. W. & Hannon, M. J. (2003). Chem. Commun. pp. 2666–2667. Web of Science CSD CrossRef Google Scholar
Li, Y., Zheng, F.-K., Liu, X., Zou, W.-Q., Guo, G.-C., Lu, C.-Z. & Huang, J.-S. (2006). Inorg. Chem. 45, 6308–6316. Web of Science CSD CrossRef PubMed 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

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