Hexa-μ2-chlorido-μ4-oxido-tetra­kis­[(3-methyl-5-phenyl-1H-pyrazole-κN2)copper(II)]

He, H.

doi:10.1107/S1600536810053663

metal-organic compounds

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Volume 67| Part 2| February 2011| Page m140

doi:10.1107/S1600536810053663

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Hexa-μ₂-chlorido-μ₄-oxido-tetrakis[(3-methyl-5-phenyl-1H-pyrazole-κN²)copper(II)]

Hongshan He ^a ^*

^aCenter for Advanced Photovoltaics, Department of Electrical Engineering and Computer Science, South Dakota State University, Brookings, SD 57007, USA
^*Correspondence e-mail: hongshan.he@sdstate.edu

(Received 19 December 2010; accepted 21 December 2010; online 8 January 2011)

The title compound, [Cu₄Cl₆O(C₁₀H₁₀N₂)₄], contains four Cu^II atoms which are bridged by six chloride anions. The central O atom is located on a crystallographic fourfold roto-inversion axis. Each Cu^II atom is coordinated by an N atom of a neutral monodentate 3-methyl-5-phenylpyrazole ligand, three Cl⁻ anions, and one O²⁻ anion. The geometry at each Cu^II atom is distorted trigonal–bipyramidal, with the three Cl⁻ ions in the equatorial plane and the N and O atoms in the axial positions.

Related literature

For the formation of trispyrazolylborate anions, see: Tekeste & Vahrenkamp (2007 ); Jacobsen & Cohen (2004 ); Puerta & Cohen (2003 ); Parkin (2004 ). For the formation of dinuclear copper compounds, see: He & Sykes (2007 ). For the formation of tetranuclear compounds, see: Keij et al. (1991 ); Liu et al. (2003 ); Chiarella et al. (2009 ).

Experimental

Crystal data

[Cu₄Cl₆O(C₁₀H₁₀N₂)₄]
M_r = 1115.66
Tetragonal, P 4/n
a = 14.5460 (6) Å
c = 11.1686 (7) Å
V = 2363.1 (3) Å³
Z = 2
Mo Kα radiation
μ = 2.16 mm⁻¹
T = 293 K
0.30 × 0.30 × 0.30 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2006 ) T_min = 0.564, T_max = 0.564
14047 measured reflections
2072 independent reflections
1184 reflections with I > 2σ(I)
R_int = 0.080

Refinement

R[F² > 2σ(F²)] = 0.067
wR(F²) = 0.194
S = 1.17
2072 reflections
136 parameters
H-atom parameters constrained
Δρ_max = 0.72 e Å⁻³
Δρ_min = −0.56 e Å⁻³

Data collection: APEX2 (Bruker, 2006); cell refinement: SAINT (Bruker, 2006); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ); software used to prepare material for publication: SHELXTL (Sheldrick, 2008), WinGX (Farrugia, 1999 ) and publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810053663/is2649sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810053663/is2649Isup2.hkl

checkCIF report

Comment top

5-Methyl-3-phenylpyrazole has been widely used as starting material for the preparation of the trispyrazolylborate anion (Tekeste & Vahrenkamp, 2007; Jacobsen & Cohen, 2004; Puerta & Cohen, 2003; Parkin, 2004). It can form a dimeric complex (He & Sykes, 2007). Reported here is a new complex when it reacts with copper chloride.

In the title compound, (I), six chloride ions hold four copper ions together with an O atom encapsulated in the center (Fig. 1). The coordination geometry around each Cu^II is identical to each other with three Cl^- in the equatorial positions and N and O atoms in the axial positions. The distances between Cu1 and three Cl atoms are 2.361 (2), 2.514 (3) and 2.377 (2) Å. The distances between Cu1 and O1 and N1 are 1.9052 (10) and 1.953 (8) Å, respectively. The N1, Cu1 and O1 atoms fall almost in a line with an angle of 177.9 (5)°. The oxygen atom is located on a crystallographic fourfold roto-inversion axis.

Related literature top

For the formation of trispyrazolylborate anions, see: Tekeste & Vahrenkamp (2007); Jacobsen & Cohen (2004); Puerta & Cohen (2003); Parkin (2004). For the formation of dimeric copper compounds, see: He & Sykes (2007). For the formation of tetracopper compounds, see: Keij et al. (1991); Liu et al. (2003); Chiarella et al. (2009).

Experimental top

5-Methyl-3-phenylpyrazole (16.0 mg, 0.1 mmol), prepared according to the literature (Puerta & Cohen, 2003), was dissolved in dichloromethane (10 ml) at room temperature. To this solution, copper(II) chloride dihydrate (8.7 mg, 0.05 mmol) in methanol (2 ml) was added. The resulting solution was stirred for two hours. The mixture was filtered and the filtrate kept at room temperature. Brown crystals were obtained after one week by slow evaporation.

Computing details top

Data collection: APEX2 (Bruker, 2006); cell refinement: SAINT (Bruker, 2006); data reduction: SAINT (Bruker, 2006); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXTL (Sheldrick, 2008), WinGX (Farrugia, 1999) and publCIF (Westrip, 2010).

Figures top

Fig. 1. The structure of the title compound with displacement ellipsoids drawn at the 50% probability level. Hydrogen atoms are drawn as small circles of arbitrary radii.

Hexa-µ₂-chlorido-µ₄-oxido-tetrakis[(3-methyl-5-phenyl-1H-pyrazole- κN²)copper(II)] top

Crystal data top

[Cu₄Cl₆O(C₁₀H₁₀N₂)₄]	D_x = 1.568 Mg m⁻³
M_r = 1115.66	Mo Kα radiation, λ = 0.71073 Å
Tetragonal, P4/n	Cell parameters from 16570 reflections
Hall symbol: -P 4a	θ = 2.3–25.0°
a = 14.5460 (6) Å	µ = 2.16 mm⁻¹
c = 11.1686 (7) Å	T = 293 K
V = 2363.1 (3) Å³	Block, brown
Z = 2	0.30 × 0.30 × 0.30 mm
F(000) = 1124

Data collection top

Bruker APEXII CCD area-detector diffractometer	2072 independent reflections
Radiation source: fine-focus sealed tube	1184 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.080
ϕ and ω scans	θ_max = 25.0°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2006)	h = −17→17
T_min = 0.564, T_max = 0.564	k = −17→17
14047 measured reflections	l = −13→13

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)] = 0.067	H-atom parameters constrained
wR(F²) = 0.194	w = 1/[σ²(F_o²) + (0.0526P)² + 14.3478P] where P = (F_o² + 2F_c²)/3
S = 1.17	(Δ/σ)_max < 0.001
2072 reflections	Δρ_max = 0.72 e Å⁻³
136 parameters	Δρ_min = −0.56 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: 0.0028 (8)

Crystal data top

[Cu₄Cl₆O(C₁₀H₁₀N₂)₄]	Z = 2
M_r = 1115.66	Mo Kα radiation
Tetragonal, P4/n	µ = 2.16 mm⁻¹
a = 14.5460 (6) Å	T = 293 K
c = 11.1686 (7) Å	0.30 × 0.30 × 0.30 mm
V = 2363.1 (3) Å³

Data collection top

Bruker APEXII CCD area-detector diffractometer	2072 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2006)	1184 reflections with I > 2σ(I)
T_min = 0.564, T_max = 0.564	R_int = 0.080
14047 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.067	0 restraints
wR(F²) = 0.194	H-atom parameters constrained
S = 1.17	w = 1/[σ²(F_o²) + (0.0526P)² + 14.3478P] where P = (F_o² + 2F_c²)/3
2072 reflections	Δρ_max = 0.72 e Å⁻³
136 parameters	Δρ_min = −0.56 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	0.72083 (7)	0.14541 (7)	0.90461 (11)	0.0567 (5)
Cl2	0.57726 (15)	0.14864 (15)	1.0031 (3)	0.0729 (8)
Cl1	0.7500	0.2500	0.7295 (3)	0.0705 (10)
N2	0.6784 (5)	0.0507 (5)	0.6812 (8)	0.070 (2)
H2	0.6890	0.1006	0.6424	0.084*
N1	0.6896 (5)	0.0413 (5)	0.8019 (8)	0.063 (2)
O1	0.7500	0.2500	1.0000	0.052 (3)
C1	0.6666 (7)	−0.0801 (7)	0.9515 (11)	0.079 (3)
H1A	0.6904	−0.0337	1.0042	0.119*
H1B	0.7046	−0.1340	0.9560	0.119*
H1C	0.6050	−0.0954	0.9749	0.119*
C2	0.6663 (6)	−0.0449 (6)	0.8269 (10)	0.063 (3)
C3	0.6412 (7)	−0.0918 (7)	0.7231 (11)	0.075 (3)
H3	0.6232	−0.1530	0.7177	0.090*
C4	0.6481 (7)	−0.0296 (7)	0.6292 (11)	0.072 (3)
C5	0.6268 (7)	−0.0344 (7)	0.5035 (11)	0.075 (3)
C6	0.5923 (10)	−0.1170 (9)	0.4580 (14)	0.120 (5)
H6	0.5854	−0.1677	0.5079	0.143*
C7	0.5686 (12)	−0.1228 (12)	0.3385 (15)	0.139 (6)
H7	0.5476	−0.1786	0.3084	0.166*
C8	0.5748 (10)	−0.0512 (12)	0.2651 (15)	0.122 (5)
H8	0.5571	−0.0566	0.1854	0.146*
C9	0.6072 (10)	0.0301 (11)	0.3078 (14)	0.120 (5)
H9	0.6116	0.0811	0.2579	0.144*
C10	0.6331 (9)	0.0355 (9)	0.4244 (13)	0.104 (4)
H10	0.6568	0.0911	0.4516	0.125*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.0436 (6)	0.0403 (6)	0.0863 (9)	−0.0028 (4)	−0.0010 (6)	−0.0064 (5)
Cl2	0.0424 (12)	0.0602 (14)	0.116 (2)	−0.0100 (10)	0.0079 (13)	−0.0219 (14)
Cl1	0.088 (2)	0.0405 (17)	0.082 (2)	−0.0115 (16)	0.000	0.000
N2	0.074 (5)	0.056 (5)	0.081 (6)	−0.014 (4)	0.002 (5)	−0.006 (4)
N1	0.051 (4)	0.043 (4)	0.096 (7)	−0.004 (3)	0.011 (4)	0.000 (4)
O1	0.039 (3)	0.039 (3)	0.077 (8)	0.000	0.000	0.000
C1	0.065 (6)	0.058 (6)	0.114 (10)	−0.016 (5)	0.001 (6)	0.009 (6)
C2	0.046 (5)	0.051 (5)	0.092 (8)	−0.001 (4)	0.009 (5)	0.008 (5)
C3	0.076 (7)	0.047 (5)	0.102 (9)	−0.013 (5)	0.000 (6)	−0.012 (6)
C4	0.066 (6)	0.054 (6)	0.097 (9)	−0.016 (5)	0.009 (6)	−0.012 (6)
C5	0.073 (7)	0.074 (7)	0.078 (8)	−0.017 (5)	0.013 (6)	−0.017 (6)
C6	0.149 (13)	0.090 (9)	0.119 (12)	−0.040 (9)	0.014 (10)	−0.039 (8)
C7	0.180 (16)	0.130 (14)	0.106 (13)	−0.057 (12)	0.008 (12)	−0.049 (11)
C8	0.108 (11)	0.142 (14)	0.115 (12)	−0.035 (10)	0.011 (9)	−0.029 (12)
C9	0.128 (12)	0.127 (12)	0.104 (11)	−0.037 (10)	−0.004 (9)	0.003 (10)
C10	0.122 (11)	0.096 (9)	0.095 (10)	−0.032 (8)	−0.014 (8)	0.004 (8)

Geometric parameters (Å, º) top

Cu1—O1	1.9052 (10)	C1—H1C	0.9600
Cu1—N1	1.953 (8)	C2—C3	1.394 (14)
Cu1—Cl2	2.361 (2)	C3—C4	1.388 (14)
Cu1—Cl2ⁱ	2.377 (2)	C3—H3	0.9300
Cu1—Cl1	2.514 (3)	C4—C5	1.439 (15)
Cl2—Cu1ⁱⁱ	2.377 (2)	C5—C10	1.350 (15)
Cl1—Cu1ⁱⁱⁱ	2.514 (3)	C5—C6	1.397 (15)
N2—N1	1.365 (11)	C6—C7	1.38 (2)
N2—C4	1.377 (11)	C6—H6	0.9300
N2—H2	0.8600	C7—C8	1.33 (2)
N1—C2	1.328 (10)	C7—H7	0.9300
O1—Cu1ⁱⁱⁱ	1.9052 (10)	C8—C9	1.359 (18)
O1—Cu1ⁱ	1.9052 (10)	C8—H8	0.9300
O1—Cu1ⁱⁱ	1.9052 (10)	C9—C10	1.358 (18)
C1—C2	1.482 (15)	C9—H9	0.9300
C1—H1A	0.9600	C10—H10	0.9300
C1—H1B	0.9600

O1—Cu1—N1	177.9 (3)	H1B—C1—H1C	109.5
O1—Cu1—Cl2	85.45 (7)	N1—C2—C3	110.7 (10)
N1—Cu1—Cl2	94.8 (2)	N1—C2—C1	121.5 (10)
O1—Cu1—Cl2ⁱ	84.98 (7)	C3—C2—C1	127.8 (9)
N1—Cu1—Cl2ⁱ	96.7 (2)	C4—C3—C2	106.9 (8)
Cl2—Cu1—Cl2ⁱ	120.86 (5)	C4—C3—H3	126.6
O1—Cu1—Cl1	85.08 (7)	C2—C3—H3	126.6
N1—Cu1—Cl1	93.0 (3)	N2—C4—C3	104.9 (9)
Cl2—Cu1—Cl1	119.98 (8)	N2—C4—C5	121.4 (10)
Cl2ⁱ—Cu1—Cl1	117.06 (8)	C3—C4—C5	133.6 (9)
Cu1—Cl2—Cu1ⁱⁱ	81.32 (8)	C10—C5—C6	115.7 (12)
Cu1ⁱⁱⁱ—Cl1—Cu1	77.85 (12)	C10—C5—C4	126.0 (10)
N1—N2—C4	111.7 (8)	C6—C5—C4	118.3 (12)
N1—N2—H2	124.1	C7—C6—C5	119.6 (15)
C4—N2—H2	124.1	C7—C6—H6	120.2
C2—N1—N2	105.8 (8)	C5—C6—H6	120.2
C2—N1—Cu1	131.9 (8)	C8—C7—C6	122.0 (15)
N2—N1—Cu1	122.0 (6)	C8—C7—H7	119.0
Cu1ⁱⁱⁱ—O1—Cu1	112.00 (7)	C6—C7—H7	119.0
Cu1ⁱⁱⁱ—O1—Cu1ⁱ	108.22 (3)	C7—C8—C9	119.3 (16)
Cu1—O1—Cu1ⁱ	108.22 (3)	C7—C8—H8	120.3
Cu1ⁱⁱⁱ—O1—Cu1ⁱⁱ	108.22 (3)	C9—C8—H8	120.3
Cu1—O1—Cu1ⁱⁱ	108.22 (3)	C10—C9—C8	118.9 (15)
Cu1ⁱ—O1—Cu1ⁱⁱ	112.00 (7)	C10—C9—H9	120.6
C2—C1—H1A	109.5	C8—C9—H9	120.6
C2—C1—H1B	109.5	C5—C10—C9	124.4 (13)
H1A—C1—H1B	109.5	C5—C10—H10	117.8
C2—C1—H1C	109.5	C9—C10—H10	117.8
H1A—C1—H1C	109.5

O1—Cu1—Cl2—Cu1ⁱⁱ	1.12 (6)	Cl1—Cu1—O1—Cu1ⁱⁱ	119.21 (2)
N1—Cu1—Cl2—Cu1ⁱⁱ	−176.7 (3)	N2—N1—C2—C3	0.8 (10)
Cl2ⁱ—Cu1—Cl2—Cu1ⁱⁱ	82.50 (10)	Cu1—N1—C2—C3	174.0 (6)
Cl1—Cu1—Cl2—Cu1ⁱⁱ	−80.53 (11)	N2—N1—C2—C1	−177.8 (8)
O1—Cu1—Cl1—Cu1ⁱⁱⁱ	0.0	Cu1—N1—C2—C1	−4.6 (13)
N1—Cu1—Cl1—Cu1ⁱⁱⁱ	179.1 (2)	N1—C2—C3—C4	−1.1 (11)
Cl2—Cu1—Cl1—Cu1ⁱⁱⁱ	81.86 (9)	C1—C2—C3—C4	177.3 (9)
Cl2ⁱ—Cu1—Cl1—Cu1ⁱⁱⁱ	−81.80 (9)	N1—N2—C4—C3	−0.6 (11)
C4—N2—N1—C2	−0.1 (10)	N1—N2—C4—C5	176.7 (9)
C4—N2—N1—Cu1	−174.1 (6)	C2—C3—C4—N2	1.0 (11)
Cl2—Cu1—N1—C2	−60.9 (8)	C2—C3—C4—C5	−175.8 (11)
Cl2ⁱ—Cu1—N1—C2	61.0 (8)	N2—C4—C5—C10	−0.3 (18)
Cl1—Cu1—N1—C2	178.7 (8)	C3—C4—C5—C10	176.0 (13)
Cl2—Cu1—N1—N2	111.4 (6)	N2—C4—C5—C6	−177.1 (11)
Cl2ⁱ—Cu1—N1—N2	−126.7 (6)	C3—C4—C5—C6	−0.7 (19)
Cl1—Cu1—N1—N2	−9.0 (6)	C10—C5—C6—C7	1 (2)
Cl2—Cu1—O1—Cu1ⁱⁱⁱ	−120.66 (8)	C4—C5—C6—C7	178.0 (13)
Cl2ⁱ—Cu1—O1—Cu1ⁱⁱⁱ	117.77 (8)	C5—C6—C7—C8	−2 (3)
Cl1—Cu1—O1—Cu1ⁱⁱⁱ	0.0	C6—C7—C8—C9	1 (3)
Cl2—Cu1—O1—Cu1ⁱ	120.13 (9)	C7—C8—C9—C10	1 (2)
Cl2ⁱ—Cu1—O1—Cu1ⁱ	−1.44 (8)	C6—C5—C10—C9	1 (2)
Cl1—Cu1—O1—Cu1ⁱ	−119.21 (2)	C4—C5—C10—C9	−175.8 (13)
Cl2—Cu1—O1—Cu1ⁱⁱ	−1.45 (8)	C8—C9—C10—C5	−2 (2)
Cl2ⁱ—Cu1—O1—Cu1ⁱⁱ	−123.01 (9)

Symmetry codes: (i) −y+1, x−1/2, −z+2; (ii) y+1/2, −x+1, −z+2; (iii) −x+3/2, −y+1/2, z.

Experimental details

Crystal data
Chemical formula	[Cu₄Cl₆O(C₁₀H₁₀N₂)₄]
M_r	1115.66
Crystal system, space group	Tetragonal, P4/n
Temperature (K)	293
a, c (Å)	14.5460 (6), 11.1686 (7)
V (Å³)	2363.1 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	2.16
Crystal size (mm)	0.30 × 0.30 × 0.30

Data collection
Diffractometer	Bruker APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2006)
T_min, T_max	0.564, 0.564
No. of measured, independent and observed [I > 2σ(I)] reflections	14047, 2072, 1184
R_int	0.080
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.067, 0.194, 1.17
No. of reflections	2072
No. of parameters	136
H-atom treatment	H-atom parameters constrained
	w = 1/[σ²(F_o²) + (0.0526P)² + 14.3478P] where P = (F_o² + 2F_c²)/3
Δρ_max, Δρ_min (e Å⁻³)	0.72, −0.56

Computer programs: APEX2 (Bruker, 2006), SAINT (Bruker, 2006), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), SHELXTL (Sheldrick, 2008), WinGX (Farrugia, 1999) and publCIF (Westrip, 2010).

Acknowledgements

This material is based upon work supported by the National Science Foundation/EPSCoR grant No. 0903804 and by the State of South Dakota.

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