Bis[2,6-bis­(2-meth­oxy­phen­yl)pyridinium] di-μ-bromido-bis­[dibromidocuprate(II)]

Sangtrirutnugul, P.; Haesuwannakij, S.; Sooksimuang, T.; Prabpai, S.; Kongsaeree, P.

doi:10.1107/S1600536811003588

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 3| March 2011| Pages m299-m300

doi:10.1107/S1600536811003588

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Bis[2,6-bis(2-methoxyphenyl)pyridinium] di-μ-bromido-bis[dibromidocuprate(II)]

Preeyanuch Sangtrirutnugul,^a ^* Setsiri Haesuwannakij,^a Thanasat Sooksimuang,^b Samran Prabpai ^a and Palangpon Kongsaeree ^a

^aDepartment of Chemistry and Center of Excellence for Innovation in Chemistry, Faculty of Science, Mahidol University, Rama VI Road, Bangkok 10400, Thailand, and ^bNational Metal and Materials Technology Center, Thailand Science Park, Klong Luang, Pathumthani, Thailand
^*Correspondence e-mail: scpsf@mahidol.ac.th

(Received 22 January 2011; accepted 27 January 2011; online 5 February 2011)

The title salt, (C₁₉H₁₈NO₂)₂[Cu₂Br₆], was obtained from an attempt to synthesize the copper(II) complex of 2,6-bis(2-methoxyphenyl)pyridine (L) from a reaction between CuBr₂ and one equivalent of L in CH₂Cl₂ at room temperature. The resulting compound is the salt of the 2,6-bis(2-methoxyphenyl)pyridinium cation and 0.5 equivalents of a hexabromidodicuprate(II) dianion. Both methoxy groups of the cationic pyridinium moiety are directed towards the N atom of the pyridine ring as a result of intramolecular N—H⋯O hydrogen bonds. The centrosymmetric hexabromidodicuprate dianion possesses a distorted tetrahedral geometry at the copper ion. The Cu—Br bond lengths are 2.3385 (7) and 2.3304 (7) Å for the terminal bromides, whereas the bond length between the Cu atom and two bridging bromides is slightly longer [2.4451 (6) Å].

Related literature

The neutral compound 2,6-bis(2-methoxyphenyl)pyridine has been previously reported (Silva et al., 1997 ) and copper(II) complexes of the related ligand 2,6-bis(2′-hydroxyphenyl)pyridine have also been characterized (Steinhauser et al., 2004 ).

Experimental

Crystal data

(C₁₉H₁₈NO₂)₂[Cu₂Br₆]
M_r = 1191.23
Orthorhombic, P b c a
a = 11.5329 (1) Å
b = 17.0104 (4) Å
c = 21.0021 (5) Å
V = 4120.18 (14) Å³
Z = 4
Mo Kα radiation
μ = 6.89 mm⁻¹
T = 298 K
0.25 × 0.20 × 0.18 mm

Data collection

Nonius KappaCCD diffractometer
Absorption correction: multi-scan (DENZO-SMN; Otwinowski & Minor, 1997 ) T_min = 0.207, T_max = 0.301
28095 measured reflections
4177 independent reflections
3240 reflections with I > 2σ(I)
R_int = 0.075

Refinement

R[F² > 2σ(F²)] = 0.042
wR(F²) = 0.104
S = 1.05
4177 reflections
235 parameters
H-atom parameters constrained
Δρ_max = 0.36 e Å⁻³
Δρ_min = −0.55 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H20⋯O1	0.96	1.90	2.625 (4)	131
N1—H20⋯O2	0.96	1.92	2.630 (4)	129

Data collection: KappaCCD Server Software (Nonius, 1997 ); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN; program(s) used to solve structure: SIR92 (Altomare et al., 1994 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: PLATON (Spek, 2009 ); software used to prepare material for publication: SHELXL97 and maXus (Mackay et al., 1999 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811003588/vn2002sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811003588/vn2002Isup2.hkl

checkCIF report

Comment top

An attempt to synthesize copper(II) complex of 2,6-bis(2-methoxyphenyl)- pyridine in CH₂Cl₂ unexpectedly yielded the ionic complex (C₉H₁₈NO₂).0.5(Cu₂Br₆). The single crystals of the title compound crystallizes in the orthorhombic unit cell in space group P_bca. Each asymmetric unit cell contains one molecule of 2,6-bis(2-methoxy- phenyl)pyridinium cation and half a molecule of hexabromodicuprate(II). Crystallographic data of the title compound reveals intramolecular N—H···O hydrogen bonds forcing both methoxy groups to be in close proximity to the nitrogen atom of the pyridinium ring (N···O distances of 2.625 (4) and 2.630 (4) Å). The pyridinium and two methoxyphenyl rings are almost co-planar, having the dihedral angles between them of 7.5 (5)° and 15.0 (5)°. In addition, weak intermolecular π-π stacking interactions between pyridine and phenyl moieties of the neighboring molecules with centroid-centroid distances of 3.649 (2) and 3.850 (2) Å are present.

Note that the centroid of the complete dianion coincides with the inversion center. Moreover, the hexabromodicuprate(II) dianion displays a distorted tetrahedral geometry at both copper(II) ions with Cu—Br bond distances of 2.3385 (7) and 2.3304 (7) Å for terminal bromides, and 2.4451 (6) Å for bridging bromides, respectively.

The neutral compound 2,6-bis(2-methoxyphenyl)pyridine has been previously reported (Silva et al., 1997) and their crystals were obtained from an ethyl acetate solution. The published crystal structure reveals that both methoxy groups are on opposite sides of the pyridine nitrogen to avoid the N···O lone pair repulsion. In addition, copper(II) complexes of the related ligand 2,6-bis(2'- hydroxyphenyl)pyridine have previously been synthesized and characterized (Steinhauser et al., 2004).

Related literature top

The neutral compound 2,6-bis(2-methoxyphenyl)pyridine has been previously reported (Silva et al., 1997) and copper(II) complexes of the related ligand 2,6-bis(2'-hydroxyphenyl)pyridine have also been characterized (Steinhauser et al., 2004).

Experimental top

The title compound, (C₉H₁₈NO₂).0.5(Cu₂Br₆) (1), was prepared from a reaction of CuBr₂ (0.5 mmol) with one equivalent of 2,6-bis(2-methoxyphenyl)pyridine (0.5 mmol) in dichloromethane (30 ml) at room temperature for 3 h. The reaction solution was filtered to remove any unreacted CuBr₂. X-ray quality single crystals were obtained from slow evaporation of a dichloromethane solution of 1 at room temperature.

Computing details top

Data collection: KappaCCD Server Software (Nonius, 1997); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN (Otwinowski & Minor, 1997); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and maXus (Mackay et al., 1999).

Figures top

Fig. 1. ORTEP diagram of the title compound (1). Displacement ellipsoids are drawn at the 30% probability level.

Bis[2,6-bis(2-methoxyphenyl)pyridinium] di-µ-bromido-bis[dibromidocuprate(II)] top

Crystal data top

(C₁₉H₁₈NO₂)₂[Cu₂Br₆]	F(000) = 2312
M_r = 1191.23	D_x = 1.920 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 32254 reflections
a = 11.5329 (1) Å	θ = 1.0–26.4°
b = 17.0104 (4) Å	µ = 6.89 mm⁻¹
c = 21.0021 (5) Å	T = 298 K
V = 4120.18 (14) Å³	Cube, dark green
Z = 4	0.25 × 0.20 × 0.18 mm

Data collection top

Nonius KappaCCD diffractometer	3240 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.075
ω scans	θ_max = 26.4°, θ_min = 2.9°
Absorption correction: multi-scan (DENZO-SMN; Otwinowski & Minor, 1997)	h = −14→14
T_min = 0.207, T_max = 0.301	k = −21→21
28095 measured reflections	l = −22→26
4177 independent reflections

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.104	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0575P)² + 1.1145P] where P = (F_o² + 2F_c²)/3
4177 reflections	(Δ/σ)_max < 0.001
235 parameters	Δρ_max = 0.36 e Å⁻³
0 restraints	Δρ_min = −0.55 e Å⁻³

Crystal data top

(C₁₉H₁₈NO₂)₂[Cu₂Br₆]	V = 4120.18 (14) Å³
M_r = 1191.23	Z = 4
Orthorhombic, Pbca	Mo Kα radiation
a = 11.5329 (1) Å	µ = 6.89 mm⁻¹
b = 17.0104 (4) Å	T = 298 K
c = 21.0021 (5) Å	0.25 × 0.20 × 0.18 mm

Data collection top

Nonius KappaCCD diffractometer	4177 independent reflections
Absorption correction: multi-scan (DENZO-SMN; Otwinowski & Minor, 1997)	3240 reflections with I > 2σ(I)
T_min = 0.207, T_max = 0.301	R_int = 0.075
28095 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	0 restraints
wR(F²) = 0.104	H-atom parameters constrained
S = 1.05	Δρ_max = 0.36 e Å⁻³
4177 reflections	Δρ_min = −0.55 e Å⁻³
235 parameters

Special details top

Experimental. multi-scan from symmetry-related measurements SORTAV (Blessing 1995)

Geometry. All standard uncertainties (except dihedral angles between l.s. planes) are estimated using the full covariance matrix. The standard uncertainties in cell dimensions are are used in calculating the standard uncertainties of bond distances, angles and torsion angles. Angles between l.s. planes have standard uncertainties calculated from atomic positional standard uncertainties; the errors in cell dimensions are not used in this case.

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

	x	y	z	U_iso*/U_eq
Br1	−0.03538 (4)	0.45904 (3)	0.07154 (2)	0.07414 (19)
Br2	0.14159 (4)	0.30603 (3)	0.00330 (2)	0.05795 (15)
Br3	0.31781 (4)	0.47771 (3)	−0.02118 (2)	0.06266 (16)
Cu1	0.12512 (4)	0.44281 (3)	−0.00337 (2)	0.05014 (16)
N1	0.3781 (2)	0.23294 (16)	0.25843 (14)	0.0384 (7)
H20	0.3754	0.2367	0.2128	0.046*
O1	0.3184 (2)	0.16507 (18)	0.15107 (14)	0.0609 (8)
O2	0.4577 (2)	0.30722 (17)	0.15766 (13)	0.0571 (7)
C1	0.2958 (3)	0.1857 (2)	0.28504 (18)	0.0438 (9)
C2	0.2983 (4)	0.1787 (3)	0.3505 (2)	0.0613 (11)
H2	0.2431	0.1451	0.3713	0.074*
C3	0.3783 (4)	0.2192 (3)	0.3857 (2)	0.0678 (12)
H3	0.3768	0.2142	0.4312	0.081*
C4	0.4595 (3)	0.2663 (2)	0.35705 (19)	0.0535 (10)
H4	0.5156	0.2941	0.3822	0.064*
C5	0.4602 (3)	0.2733 (2)	0.29171 (17)	0.0388 (8)
C6	0.2118 (3)	0.1434 (2)	0.2446 (2)	0.0461 (9)
C7	0.2227 (3)	0.1327 (2)	0.1792 (2)	0.0500 (10)
C8	0.1406 (4)	0.0902 (3)	0.1446 (3)	0.0658 (12)
H8	0.1496	0.0835	0.0995	0.079*
C9	0.0476 (4)	0.0583 (3)	0.1753 (3)	0.0768 (16)
H9	−0.0088	0.0294	0.1512	0.092*
C10	0.0341 (4)	0.0672 (3)	0.2395 (3)	0.0751 (15)
H10	−0.0311	0.0436	0.2606	0.090*
C11	0.1135 (3)	0.1099 (3)	0.2742 (2)	0.0614 (12)
H11	0.1027	0.1172	0.3191	0.074*
C12	0.3434 (4)	0.1461 (3)	0.0865 (2)	0.0712 (13)
H12A	0.4127	0.1730	0.0734	0.085*
H12B	0.2798	0.1624	0.0600	0.085*
H12C	0.3544	0.0904	0.0824	0.085*
C13	0.5483 (3)	0.3218 (2)	0.25782 (18)	0.0421 (8)
C14	0.5472 (3)	0.3374 (2)	0.19176 (19)	0.0445 (9)
C15	0.6341 (4)	0.3824 (2)	0.1641 (2)	0.0569 (11)
H15	0.6337	0.3919	0.1191	0.068*
C16	0.7214 (4)	0.4135 (3)	0.2013 (3)	0.0671 (13)
H16	0.7812	0.4448	0.1821	0.081*
C17	0.7238 (3)	0.4001 (3)	0.2657 (3)	0.0669 (13)
H17	0.7844	0.4222	0.2914	0.080*
C18	0.6385 (3)	0.3547 (2)	0.2938 (2)	0.0550 (10)
H18	0.6421	0.3458	0.3389	0.066*
C19	0.4346 (4)	0.3398 (3)	0.0959 (2)	0.0667 (12)
H19A	0.3696	0.3133	0.0772	0.080*
H19B	0.5016	0.3331	0.0693	0.080*
H19C	0.4174	0.3948	0.1000	0.080*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.0777 (3)	0.0785 (4)	0.0662 (3)	0.0310 (2)	0.0336 (2)	0.0342 (3)
Br2	0.0599 (3)	0.0497 (3)	0.0643 (3)	0.00570 (18)	0.01288 (19)	0.0059 (2)
Br3	0.0578 (3)	0.0655 (3)	0.0646 (3)	−0.00476 (19)	0.0102 (2)	0.0042 (2)
Cu1	0.0534 (3)	0.0490 (3)	0.0480 (3)	0.0075 (2)	0.0124 (2)	0.0064 (2)
N1	0.0394 (16)	0.0413 (16)	0.0344 (16)	0.0002 (12)	0.0000 (12)	0.0008 (13)
O1	0.0662 (18)	0.0702 (19)	0.0464 (18)	−0.0161 (15)	0.0017 (13)	−0.0131 (16)
O2	0.0643 (17)	0.0674 (19)	0.0395 (16)	−0.0155 (14)	−0.0049 (12)	0.0100 (14)
C1	0.0392 (19)	0.044 (2)	0.048 (2)	0.0010 (15)	0.0072 (16)	0.0039 (18)
C2	0.062 (3)	0.072 (3)	0.050 (3)	−0.013 (2)	0.011 (2)	0.007 (2)
C3	0.079 (3)	0.086 (3)	0.039 (2)	−0.009 (3)	0.003 (2)	0.004 (2)
C4	0.060 (2)	0.058 (3)	0.043 (2)	−0.0058 (19)	−0.0026 (18)	−0.005 (2)
C5	0.0388 (19)	0.0363 (19)	0.041 (2)	0.0044 (14)	−0.0021 (14)	−0.0026 (16)
C6	0.041 (2)	0.036 (2)	0.061 (3)	0.0040 (14)	0.0015 (17)	0.0058 (18)
C7	0.047 (2)	0.042 (2)	0.061 (3)	0.0006 (16)	−0.0013 (18)	−0.0037 (19)
C8	0.061 (3)	0.055 (3)	0.082 (4)	−0.004 (2)	−0.014 (2)	−0.014 (3)
C9	0.054 (3)	0.052 (3)	0.124 (5)	−0.006 (2)	−0.020 (3)	−0.012 (3)
C10	0.046 (3)	0.054 (3)	0.126 (5)	−0.0071 (19)	0.003 (3)	0.011 (3)
C11	0.045 (2)	0.054 (3)	0.085 (3)	0.0010 (19)	0.009 (2)	0.009 (2)
C12	0.089 (3)	0.071 (3)	0.054 (3)	0.001 (2)	0.002 (2)	−0.020 (2)
C13	0.0374 (18)	0.039 (2)	0.050 (2)	0.0028 (14)	−0.0009 (15)	−0.0031 (17)
C14	0.046 (2)	0.040 (2)	0.048 (2)	0.0004 (16)	0.0024 (16)	0.0020 (17)
C15	0.060 (3)	0.052 (3)	0.059 (3)	−0.001 (2)	0.014 (2)	0.010 (2)
C16	0.050 (3)	0.052 (3)	0.099 (4)	−0.008 (2)	0.012 (2)	0.008 (3)
C17	0.043 (2)	0.062 (3)	0.096 (4)	−0.006 (2)	−0.005 (2)	−0.007 (3)
C18	0.049 (2)	0.054 (2)	0.062 (3)	−0.0034 (18)	−0.0075 (19)	−0.003 (2)
C19	0.081 (3)	0.077 (3)	0.042 (3)	−0.005 (2)	−0.006 (2)	0.011 (2)

Geometric parameters (Å, º) top

Br2—Cu1	2.3385 (7)	C2—H2	0.9600
Br3—Cu1	2.3304 (7)	C19—H19A	0.9600
Br1—Cu1	2.4451 (6)	C19—H19B	0.9600
C5—N1	1.362 (4)	C19—H19C	0.9600
C5—C4	1.377 (5)	C3—H3	0.9600
C5—C13	1.490 (5)	C7—C6	1.392 (6)
O2—C14	1.356 (4)	C7—C8	1.396 (6)
O2—C19	1.435 (5)	C11—C6	1.413 (5)
O1—C7	1.367 (5)	C11—H11	0.9600
O1—C12	1.423 (5)	C12—H12A	0.9600
C14—C15	1.389 (5)	C12—H12B	0.9600
C14—C13	1.413 (5)	C12—H12C	0.9600
N1—C1	1.363 (4)	C13—C18	1.402 (5)
N1—H20	0.9600	C8—C9	1.364 (7)
C10—C9	1.365 (8)	C8—H8	0.9600
C10—C11	1.377 (7)	C18—C17	1.382 (6)
C10—H10	0.9601	C18—H18	0.9600
C4—C3	1.372 (6)	C16—C17	1.372 (7)
C4—H4	0.9600	C16—H16	0.9600
C15—C16	1.380 (6)	C17—H17	0.9600
C15—H15	0.9598	C9—H9	0.9600
C2—C3	1.368 (6)	C1—C6	1.476 (5)
C2—C1	1.380 (6)

Br3—Cu1—Br2	100.69 (2)	O1—C7—C8	122.1 (4)
Br3—Cu1—Br1	142.79 (3)	C6—C7—C8	121.3 (4)
Br2—Cu1—Br1	97.77 (2)	C10—C11—C6	121.0 (5)
N1—C5—C4	117.6 (3)	C10—C11—H11	120.1
N1—C5—C13	120.5 (3)	C6—C11—H11	118.9
C4—C5—C13	121.8 (3)	O1—C12—H12A	109.4
C14—O2—C19	118.1 (3)	O1—C12—H12B	109.4
C7—O1—C12	118.9 (3)	H12A—C12—H12B	109.5
O2—C14—C15	122.5 (4)	O1—C12—H12C	109.6
O2—C14—C13	117.0 (3)	H12A—C12—H12C	109.5
C15—C14—C13	120.5 (4)	H12B—C12—H12C	109.5
C5—N1—C1	124.8 (3)	C18—C13—C14	117.4 (4)
C5—N1—H20	120.1	C18—C13—C5	118.0 (3)
C1—N1—H20	115.2	C14—C13—C5	124.5 (3)
C9—C10—C11	120.3 (5)	C9—C8—C7	119.6 (5)
C9—C10—H10	119.9	C9—C8—H8	120.4
C11—C10—H10	119.8	C7—C8—H8	120.1
C3—C4—C5	119.4 (4)	C17—C18—C13	121.4 (4)
C3—C4—H4	120.5	C17—C18—H18	118.5
C5—C4—H4	120.1	C13—C18—H18	120.0
C16—C15—C14	120.1 (4)	C17—C16—C15	120.6 (4)
C16—C15—H15	119.8	C17—C16—H16	119.5
C14—C15—H15	120.1	C15—C16—H16	119.9
C3—C2—C1	120.6 (4)	C16—C17—C18	120.0 (4)
C3—C2—H2	120.0	C16—C17—H17	120.2
C1—C2—H2	119.4	C18—C17—H17	119.9
O2—C19—H19A	109.5	C8—C9—C10	120.9 (5)
O2—C19—H19B	109.4	C8—C9—H9	119.1
H19A—C19—H19B	109.5	C10—C9—H9	120.0
O2—C19—H19C	109.5	N1—C1—C2	116.4 (3)
H19A—C19—H19C	109.5	N1—C1—C6	120.6 (3)
H19B—C19—H19C	109.5	C2—C1—C6	123.0 (3)
C2—C3—C4	121.2 (4)	C7—C6—C11	117.0 (4)
C2—C3—H3	118.9	C7—C6—C1	124.9 (3)
C4—C3—H3	120.0	C11—C6—C1	118.1 (4)
O1—C7—C6	116.5 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H20···O1	0.96	1.90	2.625 (4)	131
N1—H20···O2	0.96	1.92	2.630 (4)	129

Experimental details

Crystal data
Chemical formula	(C₁₉H₁₈NO₂)₂[Cu₂Br₆]
M_r	1191.23
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	298
a, b, c (Å)	11.5329 (1), 17.0104 (4), 21.0021 (5)
V (Å³)	4120.18 (14)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	6.89
Crystal size (mm)	0.25 × 0.20 × 0.18

Data collection
Diffractometer	Nonius KappaCCD diffractometer
Absorption correction	Multi-scan (DENZO-SMN; Otwinowski & Minor, 1997)
T_min, T_max	0.207, 0.301
No. of measured, independent and observed [I > 2σ(I)] reflections	28095, 4177, 3240
R_int	0.075
(sin θ/λ)_max (Å⁻¹)	0.625

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.104, 1.05
No. of reflections	4177
No. of parameters	235
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.36, −0.55

Computer programs: KappaCCD Server Software (Nonius, 1997), DENZO-SMN (Otwinowski & Minor, 1997), SIR92 (Altomare et al., 1994), PLATON (Spek, 2009), SHELXL97 (Sheldrick, 2008) and maXus (Mackay et al., 1999).

Selected bond lengths (Å) top

Br2—Cu1	2.3385 (7)	Br1—Cu1	2.4451 (6)
Br3—Cu1	2.3304 (7)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H20···O1	0.96	1.90	2.625 (4)	131
N1—H20···O2	0.96	1.92	2.630 (4)	129

Acknowledgements

The authors acknowledge financial support from the Young Scientist and Technologist Programme (YSTP), the Center of Excellence for Innovation in Chemistry (PERCH-CIC) and the Office of the Higher Education Commission and Mahidol University under the National Research Universities Initiative.

References

Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435. CrossRef Web of Science IUCr Journals Google Scholar
Mackay, S., Gilmore, C. J., Edwards, C., Stewart, N. & Shankland, K. (1999). maXus. Bruker–Nonius, Delft, The Netherlands, MacScience, Yokohama, Japan, and The University of Glasgow, Scotland. Google Scholar
Nonius (1997). KappaCCD Server Software. Nonius BV, Delft, The Netherlands. Google Scholar
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307–326. New York: Academic Press. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Silva, A. M. S., Almeida, L. M. P. M., Cavaleiro, J. A. S., Foces-Foces, C., Llamas-Saiz, A. L., Fontenas, C., Jagerovic, N. & Elguero, J. (1997). Tetrahedron, 53, 11645–11658. CSD CrossRef CAS Web of Science Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Steinhauser, S., Heinz, U., Sander, J. & Hegetschweiler, K. (2004). Z. Anorg. Allg. Chem. 630, 1829–1838. Web of Science CSD CrossRef CAS Google Scholar

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Volume 67| Part 3| March 2011| Pages m299-m300

doi:10.1107/S1600536811003588

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

Bis[2,6-bis­­(2-meth­­oxy­phen­yl)pyridinium] di-μ-bromido-bis­­[di­bromidocuprate(II)]

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

metal-organic compounds

Bis[2,6-bis(2-methoxyphenyl)pyridinium] di-μ-bromido-bis[dibromidocuprate(II)]