Bis[chloridobis(1,10-phenanthroline)copper(II)] penta­cyanido­nitro­soferrate(II) di­methyl­formamide monosolvate

Rusanova, J.A.; Kozachuk, O.V.; Dyakonenko, V.V.

doi:10.1107/S1600536813015547

metal-organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 69| Part 7| July 2013| Pages m391-m392

https://doi.org/10.1107/S1600536813015547

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Bis[chloridobis(1,10-phenanthroline)copper(II)] pentacyanidonitrosoferrate(II) dimethylformamide monosolvate

Julia A. Rusanova,^a Olesia V. Kozachuk ^a ^* and Viktoriya V. Dyakonenko ^b

^aTaras Shevchenko National University, Department of Chemistry, Volodymyrska str. 64/13, 01601 Kyiv, Ukraine, and ^bSTC, "Institute for Single Crystals", National Academy of Sciences of Ukraine, Lenina ave. 60, Kharkov 61001, Ukraine
^*Correspondence e-mail: kozachuk_o@yahoo.com

(Received 21 May 2013; accepted 4 June 2013; online 15 June 2013)

The title complex [CuCl(C₁₂H₈N₂)₂]₂[Fe(CN)₅(NO)]·C₃H₇NO, consists of discrete [Cu(phen)₂Cl]⁺ cations (phen is 1,10-phenanthroline), [Fe(CN)₅NO]²⁻ anions and one dimethylformamide (DMF) solvent molecule of crystallization per asymmetric unit. The Cu^II atom is coordinated by two phenanthroline ligands and one chloride ion in a distorted trigonal–bipyramidal geometry. The dihedral angle between the phen ligands is 77.92 (7)°. The cation charge is balanced by a disordered nitroprusside counter-anion with the Fe^II atom located on an inversion center with a slightly distorted octahedral coordination geometry. In the crystal, weak C—H⋯N and C—H⋯Cl hydrogen bonds connect anions and cations into a two-dimensional network parallel to (100). In addition, π–π stacking interactions are observed with centroid–centroid distances in the range 3.565 (2)–3.760 (3)Å. The dimethylformamide solvent molecule was refined as disordered about an inversion center.

Related literature

For background to the direct synthesis of coordination compounds, see: Buvaylo et al. (2005 ); Makhankova et al. (2002 ); Nesterova et al. (2004 , 2005 , 2008 ); Pryma et al. (2003 ); Vinogradova et al. (2002 ); Vassilyeva et al. (1997 ). For the structures of related complexes, see: Nikitina et al. (2008 ); Vreshch et al. (2009 ); Onawumi et al. (2010 ); Sui et al. (2006 ); Xiao et al. (2004 ); Soria et al. (2002 ); Shevyakova et al. (2002 ).

Experimental

Crystal data

[CuCl(C₁₂H₈N₂)₂]₂[Fe(CN)₅(NO)]·C₃H₇NO
M_r = 1207.85
Triclinic, $[P \overline 1]$
a = 9.9645 (13) Å
b = 10.6001 (18) Å
c = 12.623 (2) Å
α = 79.585 (14)°
β = 84.896 (12)°
γ = 82.047 (12)°
V = 1295.9 (4) Å³
Z = 1
Mo Kα radiation
μ = 1.25 mm⁻¹
T = 293 K
0.50 × 0.40 × 0.20 mm

Data collection

Oxford Diffraction Xcalibur 3 diffractometer
Absorption correction: numerical (CrysAlis PRO; Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ) T_min = 0.575, T_max = 0.789
11289 measured reflections
5647 independent reflections
2685 reflections with I > 2σ(I)
R_int = 0.041

Refinement

R[F² > 2σ(F²)] = 0.061
wR(F²) = 0.182
S = 0.99
5647 reflections
366 parameters
5 restraints
H-atom parameters constrained
Δρ_max = 0.73 e Å⁻³
Δρ_min = −0.61 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C12—H12⋯Cl1ⁱ	0.93	2.82	3.701 (6)	159
C23—H23⋯N6ⁱⁱ	0.93	2.52	3.425 (7)	163
Symmetry codes: (i) -x+1, -y+2, -z; (ii) -x, -y+1, -z+1.

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL and PLATON (Spek, 2009 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: https://doi.org/10.1107/S1600536813015547/lh5620sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536813015547/lh5620Isup2.hkl

checkCIF report

Comment top

This work is a continuation of our research in the field of direct synthesis of coordination compounds (Buvaylo et al., 2005; Makhankova et al., 2002; Nesterova et al., 2004,2005,2008; Pryma et al., 2003; Vinogradova et al., 2002; Vassilyeva et al., 1997). It was shown recently the possibility of using anionic complexes as a source of metalloligands or the second metal in direct synthesis of heterometallic compounds (Nikitina et al., 2008; Vreshch et al., 2009).

In this paper we present a novel Cu/Fe heterometallic ionic complex [CuCl(phen)₂][Fe(CN)₅NO]^.DMF which consists of discrete [CuCl(phen)₂]⁺ and [Fe(CN)₅NO]^2- ions (Fig. 1) as well as dimethylformamide solvent molecules. The Cu^II ion adopts a distorted trigonal–bipyramidal environment by coordinating with four nitrogen atoms from two phen ligands and chlorine atom. The dihedral angle between the two phen ligands (77.92 (7)° ) as well as the range of Cu—N bond distances of 1.996 (3) - 2.177 (4) Å is in good agreement with the previously reported values for analagous complexes (Onawumi et al., 2010; Sui et al., 2006; Xiao et al., 2004). The nitroprusside ion lies across an inversion center. Therefore, the CN and NO groups occupy the axial positions with equal occupancies. It has the usual distorted octahedral, pagoda-like, conformation with average Fe—C and Fe—N bond distances of 1.90 Å and 1.78 Å respectively, in a good agreement with literature values (Soria et al. (2002); Shevyakova et al. (2002). In the crystal, weak C—H···N and C—H···Cl hydrogen bonds connect anions and cations into a two-dimensional network parallel to (100) (Fig. 2). In addition, π···π stacking interactions are observed with centroid to centroid distances in the range 3.565 (2)–3.760 (3)Å.

Related literature top

For background to the direct synthesis of coordination compounds, see: Buvaylo et al. (2005); Makhankova et al. (2002); Nesterova et al. (2004, 2005, 2008); Pryma et al. (2003); Vinogradova et al. (2002); Vassilyeva et al. (1997). For the structures of related complexes, see: Nikitina et al. (2008); Vreshch et al. (2009); Onawumi et al. (2010); Sui et al. (2006); Xiao et al. (2004); Soria et al. (2002); Shevyakova et al. (2002).

Experimental top

Copper powder (0.159 g, 2.50 mmol), Na₂[Fe(CN)₅(NO)]^.2H₂O (0.372 g, 1.25 mmol) and phen^.HCl^.H₂O (1.17 g, 5.00 mmol) in DMF (20 ml) were heated to 323–333 K and stirred magnetically until total dissolution of copper was observed (75 min). Green crystals suitable for X-ray crystallography were isolated in four days. The crystals (0.18 g, yield 14%) were filtered off, washed with dry methanol, and finally dried in vacuo at room temperature.

Structure description top

For background to the direct synthesis of coordination compounds, see: Buvaylo et al. (2005); Makhankova et al. (2002); Nesterova et al. (2004, 2005, 2008); Pryma et al. (2003); Vinogradova et al. (2002); Vassilyeva et al. (1997). For the structures of related complexes, see: Nikitina et al. (2008); Vreshch et al. (2009); Onawumi et al. (2010); Sui et al. (2006); Xiao et al. (2004); Soria et al. (2002); Shevyakova et al. (2002).

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2010); cell refinement: CrysAlis PRO (Oxford Diffraction, 2010); data reduction: CrysAlis PRO (Oxford Diffraction, 2010); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

	Fig. 1. The molecular structure of the title compound with displacement ellipsoids drawn at the 50% probability level. Symmetry code (A): -x+1, -y+1, -z+1.
	Fig. 2. Part of the crystal structure with weak hydrogen bonds shown as dashed lines. Only H atoms involved in hydrogen bonds are shown. The disordered solvent molecule is not shown as it is not involved in the hydrogen bond motif.

Bis[chloridobis(1,10-phenanthroline)copper(II)] pentacyanidonitrosoferrate(II) dimethylformamide monosolvate top

Crystal data top

[CuCl(C₁₂H₈N₂)₂]₂[Fe(CN)₅(NO)]·C₃H₇NO	V = 1295.9 (4) Å³
M_r = 1207.85	Z = 1
Triclinic, P1	F(000) = 614
Hall symbol: -P 1	D_x = 1.548 Mg m⁻³
a = 9.9645 (13) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.6001 (18) Å	µ = 1.25 mm⁻¹
c = 12.623 (2) Å	T = 293 K
α = 79.585 (14)°	Block, green
β = 84.896 (12)°	0.50 × 0.40 × 0.20 mm
γ = 82.047 (12)°

Data collection top

Oxford Diffraction Xcalibur 3 diffractometer	5647 independent reflections
Radiation source: fine-focus sealed tube	2685 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.041
Detector resolution: 16.1827 pixels mm^-1	θ_max = 27.0°, θ_min = 3.9°
ω–scans	h = −12→12
Absorption correction: numerical (CrysAlis PRO; Oxford Diffraction, 2010)	k = −13→13
T_min = 0.575, T_max = 0.789	l = −16→16
11289 measured 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)] = 0.061	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.182	H-atom parameters constrained
S = 0.99	w = 1/[σ²(F_o²) + (0.090P)²] where P = (F_o² + 2F_c²)/3
5647 reflections	(Δ/σ)_max = 0.001
366 parameters	Δρ_max = 0.73 e Å⁻³
5 restraints	Δρ_min = −0.61 e Å⁻³

Crystal data top

[CuCl(C₁₂H₈N₂)₂]₂[Fe(CN)₅(NO)]·C₃H₇NO	γ = 82.047 (12)°
M_r = 1207.85	V = 1295.9 (4) Å³
Triclinic, P1	Z = 1
a = 9.9645 (13) Å	Mo Kα radiation
b = 10.6001 (18) Å	µ = 1.25 mm⁻¹
c = 12.623 (2) Å	T = 293 K
α = 79.585 (14)°	0.50 × 0.40 × 0.20 mm
β = 84.896 (12)°

Data collection top

Oxford Diffraction Xcalibur 3 diffractometer	5647 independent reflections
Absorption correction: numerical (CrysAlis PRO; Oxford Diffraction, 2010)	2685 reflections with I > 2σ(I)
T_min = 0.575, T_max = 0.789	R_int = 0.041
11289 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.061	5 restraints
wR(F²) = 0.182	H-atom parameters constrained
S = 0.99	Δρ_max = 0.73 e Å⁻³
5647 reflections	Δρ_min = −0.61 e Å⁻³
366 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	Occ. (<1)
Cu1	0.17993 (5)	1.01179 (6)	0.25097 (5)	0.0663 (2)
Fe1	0.5000	0.5000	0.5000	0.0698 (3)
Cl1	0.04963 (14)	1.13793 (15)	0.12224 (12)	0.0907 (4)
N1	0.3265 (4)	1.1266 (4)	0.2215 (3)	0.0620 (9)
N2	0.3436 (4)	0.8814 (4)	0.1883 (3)	0.0672 (10)
N3	0.0513 (3)	0.8798 (4)	0.2939 (3)	0.0644 (10)
N4	0.2017 (3)	0.9736 (3)	0.4164 (3)	0.0567 (9)
C25	0.6109 (5)	0.4836 (4)	0.3720 (5)	0.0657 (12)
N5	0.6773 (4)	0.4748 (5)	0.2946 (4)	0.0842 (12)
C26	0.3406 (5)	0.5273 (5)	0.4171 (4)	0.0672 (12)
N6	0.2486 (4)	0.5418 (4)	0.3662 (4)	0.0821 (12)
C27	0.514 (4)	0.696 (3)	0.474 (4)	0.066 (6)	0.50
N7	0.5204 (17)	0.796 (3)	0.446 (3)	0.107 (9)	0.50
N7B	0.507 (3)	0.660 (2)	0.471 (3)	0.057 (5)	0.50
O7B	0.517 (2)	0.776 (2)	0.457 (2)	0.123 (8)	0.50
C1	0.3150 (5)	1.2477 (5)	0.2380 (4)	0.0752 (13)
H1	0.2321	1.2846	0.2654	0.090*
C2	0.4228 (6)	1.3221 (6)	0.2157 (4)	0.0824 (15)
H2	0.4134	1.4050	0.2323	0.099*
C3	0.5410 (6)	1.2716 (6)	0.1697 (4)	0.0872 (17)
H3	0.6121	1.3215	0.1520	0.105*
C4	0.5573 (4)	1.1453 (6)	0.1485 (4)	0.0694 (13)
C5	0.4460 (4)	1.0740 (5)	0.1772 (3)	0.0590 (11)
C6	0.4538 (4)	0.9441 (5)	0.1594 (3)	0.0605 (11)
C7	0.5754 (5)	0.8866 (6)	0.1118 (4)	0.0725 (14)
C8	0.5751 (7)	0.7591 (7)	0.0950 (4)	0.0942 (19)
H8	0.6514	0.7168	0.0625	0.113*
C9	0.4641 (7)	0.6979 (6)	0.1260 (5)	0.0972 (18)
H9	0.4648	0.6129	0.1163	0.117*
C10	0.3494 (6)	0.7617 (5)	0.1723 (4)	0.0829 (15)
H10	0.2737	0.7183	0.1928	0.100*
C11	0.6773 (5)	1.0833 (8)	0.1005 (4)	0.0872 (17)
H11	0.7523	1.1281	0.0820	0.105*
C12	0.6851 (5)	0.9618 (7)	0.0812 (4)	0.0874 (18)
H12	0.7640	0.9259	0.0471	0.105*
C13	−0.0238 (5)	0.8380 (5)	0.2298 (5)	0.0808 (15)
H13	−0.0229	0.8740	0.1569	0.097*
C14	−0.1058 (5)	0.7390 (5)	0.2707 (5)	0.0840 (15)
H14	−0.1585	0.7106	0.2246	0.101*
C15	−0.1078 (5)	0.6856 (5)	0.3758 (5)	0.0766 (14)
H15	−0.1617	0.6204	0.4027	0.092*
C16	−0.0292 (4)	0.7284 (4)	0.4436 (4)	0.0641 (12)
C17	0.0489 (4)	0.8265 (4)	0.3995 (4)	0.0600 (11)
C18	0.1300 (4)	0.8767 (4)	0.4657 (4)	0.0559 (10)
C19	0.1308 (4)	0.8260 (4)	0.5758 (4)	0.0611 (11)
C20	0.2095 (5)	0.8823 (5)	0.6371 (4)	0.0741 (13)
H20	0.2116	0.8539	0.7111	0.089*
C21	0.2825 (5)	0.9787 (5)	0.5879 (4)	0.0753 (13)
H21	0.3356	1.0154	0.6281	0.090*
C22	0.2776 (4)	1.0221 (5)	0.4772 (4)	0.0655 (12)
H22	0.3290	1.0872	0.4446	0.079*
C23	−0.0211 (5)	0.6775 (5)	0.5573 (4)	0.0723 (13)
H23	−0.0690	0.6091	0.5880	0.087*
C24	0.0522 (5)	0.7251 (5)	0.6187 (4)	0.0745 (14)
H24	0.0523	0.6916	0.6920	0.089*
N8	0.0000	0.5000	1.0000	0.157 (4)*
O1	−0.2091 (11)	0.465 (2)	1.004 (2)	0.273 (9)*	0.50
C28	−0.1053 (13)	0.483 (3)	0.9484 (13)	0.213 (10)*	0.50
H28A	−0.1030	0.4841	0.8688	0.256*	0.50
C29	0.015 (2)	0.504 (2)	1.1107 (9)	0.177 (8)*	0.50
H29A	−0.0724	0.4960	1.1561	0.212*	0.50
H29B	0.0843	0.4305	1.1378	0.212*	0.50
H29C	0.0475	0.5876	1.1150	0.212*	0.50
C30	0.1174 (18)	0.512 (2)	0.9282 (17)	0.186 (8)*	0.50
H30A	0.0824	0.5077	0.8573	0.223*	0.50
H30B	0.1544	0.5962	0.9235	0.223*	0.50
H30C	0.1912	0.4391	0.9462	0.223*	0.50

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.0579 (3)	0.0790 (4)	0.0627 (4)	−0.0218 (3)	0.0013 (3)	−0.0064 (3)
Fe1	0.0523 (5)	0.0874 (7)	0.0730 (7)	−0.0208 (5)	0.0005 (4)	−0.0155 (5)
Cl1	0.0809 (8)	0.1060 (11)	0.0834 (9)	−0.0154 (7)	−0.0016 (7)	−0.0103 (8)
N1	0.058 (2)	0.071 (3)	0.059 (2)	−0.0179 (18)	0.0037 (17)	−0.010 (2)
N2	0.066 (2)	0.077 (3)	0.053 (2)	−0.014 (2)	−0.0005 (18)	0.003 (2)
N3	0.057 (2)	0.072 (2)	0.065 (2)	−0.0181 (18)	−0.0070 (18)	−0.005 (2)
N4	0.0478 (17)	0.064 (2)	0.059 (2)	−0.0160 (16)	0.0040 (16)	−0.0101 (18)
C25	0.053 (2)	0.063 (3)	0.084 (3)	−0.010 (2)	−0.010 (2)	−0.016 (3)
N5	0.065 (2)	0.105 (3)	0.084 (3)	−0.012 (2)	0.001 (2)	−0.025 (3)
C26	0.057 (3)	0.063 (3)	0.077 (3)	−0.015 (2)	0.013 (2)	−0.003 (3)
N6	0.062 (2)	0.096 (3)	0.085 (3)	−0.021 (2)	−0.003 (2)	0.001 (3)
C27	0.072 (9)	0.048 (17)	0.091 (11)	−0.030 (11)	0.006 (7)	−0.033 (14)
N7	0.060 (7)	0.068 (14)	0.19 (2)	−0.003 (7)	−0.031 (10)	0.001 (11)
N7B	0.047 (5)	0.043 (12)	0.092 (8)	−0.016 (8)	−0.010 (5)	−0.028 (10)
O7B	0.186 (15)	0.047 (8)	0.140 (13)	−0.058 (8)	0.040 (10)	−0.017 (9)
C1	0.073 (3)	0.082 (4)	0.072 (3)	−0.020 (3)	0.009 (3)	−0.014 (3)
C2	0.094 (4)	0.086 (4)	0.073 (3)	−0.035 (3)	0.009 (3)	−0.019 (3)
C3	0.089 (4)	0.111 (5)	0.072 (3)	−0.058 (3)	−0.008 (3)	−0.009 (3)
C4	0.054 (2)	0.106 (4)	0.050 (3)	−0.021 (3)	−0.006 (2)	−0.005 (3)
C5	0.050 (2)	0.084 (3)	0.043 (2)	−0.021 (2)	−0.0032 (18)	−0.001 (2)
C6	0.063 (3)	0.076 (3)	0.040 (2)	−0.004 (2)	−0.009 (2)	−0.004 (2)
C7	0.065 (3)	0.096 (4)	0.051 (3)	0.006 (3)	−0.016 (2)	−0.003 (3)
C8	0.098 (4)	0.106 (5)	0.065 (3)	0.032 (4)	−0.010 (3)	−0.010 (3)
C9	0.132 (5)	0.075 (4)	0.075 (4)	0.007 (4)	−0.009 (4)	0.001 (3)
C10	0.109 (4)	0.071 (4)	0.066 (3)	−0.020 (3)	−0.003 (3)	−0.001 (3)
C11	0.053 (3)	0.152 (6)	0.059 (3)	−0.026 (3)	0.000 (2)	−0.014 (4)
C12	0.052 (3)	0.152 (6)	0.056 (3)	0.003 (3)	−0.008 (2)	−0.019 (4)
C13	0.070 (3)	0.100 (4)	0.079 (3)	−0.023 (3)	−0.015 (3)	−0.015 (3)
C14	0.075 (3)	0.091 (4)	0.096 (4)	−0.033 (3)	−0.015 (3)	−0.023 (3)
C15	0.056 (3)	0.071 (3)	0.104 (4)	−0.014 (2)	−0.007 (3)	−0.012 (3)
C16	0.045 (2)	0.059 (3)	0.087 (3)	−0.011 (2)	0.003 (2)	−0.010 (3)
C17	0.047 (2)	0.062 (3)	0.069 (3)	−0.0097 (19)	0.000 (2)	−0.007 (2)
C18	0.044 (2)	0.062 (3)	0.061 (3)	−0.0095 (19)	0.0022 (19)	−0.008 (2)
C19	0.052 (2)	0.067 (3)	0.061 (3)	−0.007 (2)	0.003 (2)	−0.004 (2)
C20	0.074 (3)	0.092 (4)	0.055 (3)	−0.013 (3)	−0.002 (2)	−0.010 (3)
C21	0.076 (3)	0.089 (4)	0.068 (3)	−0.021 (3)	−0.011 (3)	−0.020 (3)
C22	0.062 (2)	0.071 (3)	0.065 (3)	−0.018 (2)	−0.001 (2)	−0.007 (2)
C23	0.063 (3)	0.070 (3)	0.079 (3)	−0.020 (2)	0.009 (3)	0.003 (3)
C24	0.067 (3)	0.079 (3)	0.070 (3)	−0.014 (3)	0.009 (2)	0.004 (3)

Geometric parameters (Å, º) top

Cu1—N1	1.996 (3)	C11—H11	0.9300
Cu1—N3	1.998 (4)	C12—H12	0.9300
Cu1—N4	2.079 (4)	C13—C14	1.415 (7)
Cu1—N2	2.177 (4)	C13—H13	0.9300
Cu1—Cl1	2.2855 (16)	C14—C15	1.345 (7)
Fe1—N7B	1.68 (2)	C14—H14	0.9300
Fe1—N7Bⁱ	1.68 (2)	C15—C16	1.382 (7)
Fe1—C25ⁱ	1.895 (6)	C15—H15	0.9300
Fe1—C25	1.895 (6)	C16—C17	1.391 (6)
Fe1—C26ⁱ	1.939 (6)	C16—C23	1.444 (7)
Fe1—C26	1.939 (6)	C17—C18	1.427 (6)
Fe1—C27	2.07 (3)	C18—C19	1.397 (6)
Fe1—C27ⁱ	2.07 (3)	C19—C20	1.405 (7)
N1—C1	1.325 (6)	C19—C24	1.413 (6)
N1—C5	1.361 (5)	C20—C21	1.362 (7)
N2—C10	1.313 (6)	C20—H20	0.9300
N2—C6	1.351 (6)	C21—C22	1.393 (7)
N3—C13	1.320 (6)	C21—H21	0.9300
N3—C17	1.350 (6)	C22—H22	0.9300
N4—C22	1.334 (6)	C23—C24	1.317 (7)
N4—C18	1.358 (5)	C23—H23	0.9300
C25—N5	1.141 (6)	C24—H24	0.9300
C26—N6	1.143 (6)	N8—C28ⁱⁱ	1.333 (3)
C27—O7B	0.83 (4)	N8—C28	1.333 (3)
C27—N7	1.06 (4)	N8—C30ⁱⁱ	1.421 (9)
N7—N7B	1.45 (4)	N8—C30	1.421 (9)
N7B—O7B	1.23 (3)	N8—C29	1.426 (9)
C1—C2	1.398 (7)	N8—C29ⁱⁱ	1.426 (9)
C1—H1	0.9300	O1—C28	1.212 (3)
C2—C3	1.351 (8)	O1—C30ⁱⁱ	1.38 (3)
C2—H2	0.9300	C28—C29ⁱⁱ	1.13 (2)
C3—C4	1.397 (8)	C28—C30ⁱⁱ	1.56 (2)
C3—H3	0.9300	C28—H28A	1.0001
C4—C5	1.412 (6)	C29—C28ⁱⁱ	1.13 (2)
C4—C11	1.423 (8)	C29—C30ⁱⁱ	1.49 (2)
C5—C6	1.425 (7)	C29—H29A	1.0000
C6—C7	1.414 (6)	C29—H29B	0.9999
C7—C8	1.406 (8)	C29—H29C	1.0000
C7—C12	1.426 (8)	C30—O1ⁱⁱ	1.38 (3)
C8—C9	1.352 (8)	C30—C29ⁱⁱ	1.49 (2)
C8—H8	0.9300	C30—C28ⁱⁱ	1.56 (2)
C9—C10	1.383 (8)	C30—H30A	1.0000
C9—H9	0.9300	C30—H30B	1.0000
C10—H10	0.9300	C30—H30C	1.0000
C11—C12	1.344 (8)

N1—Cu1—N3	171.91 (15)	N3—C13—H13	119.6
N1—Cu1—N4	93.42 (14)	C14—C13—H13	119.6
N3—Cu1—N4	80.94 (14)	C15—C14—C13	120.3 (5)
N1—Cu1—N2	80.03 (16)	C15—C14—H14	119.8
N3—Cu1—N2	95.56 (15)	C13—C14—H14	119.8
N4—Cu1—N2	103.41 (14)	C14—C15—C16	119.4 (5)
N1—Cu1—Cl1	92.87 (12)	C14—C15—H15	120.3
N3—Cu1—Cl1	95.13 (11)	C16—C15—H15	120.3
N4—Cu1—Cl1	142.15 (10)	C15—C16—C17	118.0 (5)
N2—Cu1—Cl1	114.45 (11)	C15—C16—C23	124.6 (4)
N7B—Fe1—N7Bⁱ	180.000 (3)	C17—C16—C23	117.4 (4)
N7B—Fe1—C25ⁱ	92.0 (13)	N3—C17—C16	122.6 (4)
N7Bⁱ—Fe1—C25ⁱ	88.0 (13)	N3—C17—C18	116.7 (4)
N7B—Fe1—C25	88.0 (13)	C16—C17—C18	120.6 (4)
N7Bⁱ—Fe1—C25	92.0 (13)	N4—C18—C19	123.8 (4)
C25ⁱ—Fe1—C25	180.000 (1)	N4—C18—C17	116.8 (4)
N7B—Fe1—C26ⁱ	91.7 (10)	C19—C18—C17	119.3 (4)
N7Bⁱ—Fe1—C26ⁱ	88.3 (10)	C18—C19—C20	116.5 (4)
C25ⁱ—Fe1—C26ⁱ	89.34 (19)	C18—C19—C24	119.1 (4)
C25—Fe1—C26ⁱ	90.66 (19)	C20—C19—C24	124.4 (5)
N7B—Fe1—C26	88.3 (10)	C21—C20—C19	119.9 (5)
N7Bⁱ—Fe1—C26	91.7 (10)	C21—C20—H20	120.1
C25ⁱ—Fe1—C26	90.66 (19)	C19—C20—H20	120.1
C25—Fe1—C26	89.34 (19)	C20—C21—C22	119.8 (5)
C26ⁱ—Fe1—C26	180.000 (1)	C20—C21—H21	120.1
N7B—Fe1—C27	4 (2)	C22—C21—H21	120.1
N7Bⁱ—Fe1—C27	176 (2)	N4—C22—C21	122.2 (4)
C25ⁱ—Fe1—C27	89.7 (13)	N4—C22—H22	118.9
C25—Fe1—C27	90.3 (13)	C21—C22—H22	118.9
C26ⁱ—Fe1—C27	88.5 (12)	C24—C23—C16	121.9 (4)
C26—Fe1—C27	91.5 (12)	C24—C23—H23	119.1
N7B—Fe1—C27ⁱ	176 (2)	C16—C23—H23	119.1
N7Bⁱ—Fe1—C27ⁱ	4 (2)	C23—C24—C19	121.6 (5)
C25ⁱ—Fe1—C27ⁱ	90.3 (13)	C23—C24—H24	119.2
C25—Fe1—C27ⁱ	89.7 (13)	C19—C24—H24	119.2
C26ⁱ—Fe1—C27ⁱ	91.5 (12)	C28ⁱⁱ—N8—C28	180.000 (4)
C26—Fe1—C27ⁱ	88.5 (12)	C28ⁱⁱ—N8—C30ⁱⁱ	111.0 (11)
C27—Fe1—C27ⁱ	180.000 (4)	C28—N8—C30ⁱⁱ	69.0 (11)
C1—N1—C5	118.9 (4)	C28ⁱⁱ—N8—C30	69.0 (11)
C1—N1—Cu1	125.8 (3)	C28—N8—C30	111.0 (11)
C5—N1—Cu1	115.3 (3)	C30ⁱⁱ—N8—C30	180.000 (5)
C10—N2—C6	118.9 (4)	C28ⁱⁱ—N8—C29	48.1 (10)
C10—N2—Cu1	131.9 (4)	C28—N8—C29	131.9 (10)
C6—N2—Cu1	109.2 (3)	C30ⁱⁱ—N8—C29	62.9 (11)
C13—N3—C17	118.9 (4)	C30—N8—C29	117.1 (11)
C13—N3—Cu1	126.9 (4)	C28ⁱⁱ—N8—C29ⁱⁱ	131.9 (10)
C17—N3—Cu1	114.1 (3)	C28—N8—C29ⁱⁱ	48.1 (10)
C22—N4—C18	117.7 (4)	C30ⁱⁱ—N8—C29ⁱⁱ	117.1 (11)
C22—N4—Cu1	131.1 (3)	C30—N8—C29ⁱⁱ	62.9 (11)
C18—N4—Cu1	111.1 (3)	C29—N8—C29ⁱⁱ	180.000 (7)
N5—C25—Fe1	179.4 (5)	C28—O1—C30ⁱⁱ	73.7 (8)
N6—C26—Fe1	178.2 (5)	C29ⁱⁱ—C28—O1	173.4 (12)
O7B—C27—N7	4 (3)	C29ⁱⁱ—C28—N8	70.3 (7)
O7B—C27—Fe1	174 (5)	O1—C28—N8	116.3 (9)
N7—C27—Fe1	170 (4)	C29ⁱⁱ—C28—C30ⁱⁱ	128.3 (8)
C27—N7—N7B	7 (4)	O1—C28—C30ⁱⁱ	58.2 (9)
O7B—N7B—N7	4 (2)	N8—C28—C30ⁱⁱ	58.1 (7)
O7B—N7B—Fe1	175 (3)	C29ⁱⁱ—C28—H28A	53.9
N7—N7B—Fe1	177 (2)	O1—C28—H28A	119.6
C27—O7B—N7B	7 (5)	N8—C28—H28A	124.1
N1—C1—C2	122.5 (5)	C30ⁱⁱ—C28—H28A	175.9
N1—C1—H1	118.7	C28ⁱⁱ—C29—N8	61.6 (6)
C2—C1—H1	118.7	C28ⁱⁱ—C29—C30ⁱⁱ	120.0 (10)
C3—C2—C1	118.9 (5)	N8—C29—C30ⁱⁱ	58.4 (7)
C3—C2—H2	120.5	C28ⁱⁱ—C29—H29A	173.5
C1—C2—H2	120.5	N8—C29—H29A	112.6
C2—C3—C4	120.7 (5)	C30ⁱⁱ—C29—H29A	54.2
C2—C3—H3	119.7	C28ⁱⁱ—C29—H29B	76.0
C4—C3—H3	119.7	N8—C29—H29B	107.6
C3—C4—C5	117.3 (4)	C30ⁱⁱ—C29—H29B	124.3
C3—C4—C11	125.0 (5)	H29A—C29—H29B	109.5
C5—C4—C11	117.7 (5)	C28ⁱⁱ—C29—H29C	71.1
N1—C5—C4	121.6 (4)	N8—C29—H29C	108.2
N1—C5—C6	117.2 (4)	C30ⁱⁱ—C29—H29C	126.2
C4—C5—C6	121.2 (4)	H29A—C29—H29C	109.5
N2—C6—C7	122.8 (5)	H29B—C29—H29C	109.5
N2—C6—C5	118.2 (4)	O1ⁱⁱ—C30—N8	100.9 (13)
C7—C6—C5	119.0 (4)	O1ⁱⁱ—C30—C29ⁱⁱ	159.1 (13)
C8—C7—C6	115.9 (5)	N8—C30—C29ⁱⁱ	58.7 (7)
C8—C7—C12	125.3 (5)	O1ⁱⁱ—C30—C28ⁱⁱ	48.1 (8)
C6—C7—C12	118.7 (5)	N8—C30—C28ⁱⁱ	52.8 (6)
C9—C8—C7	120.1 (5)	C29ⁱⁱ—C30—C28ⁱⁱ	111.5 (8)
C9—C8—H8	119.9	O1ⁱⁱ—C30—H30A	156.1
C7—C8—H8	119.9	N8—C30—H30A	102.4
C8—C9—C10	120.1 (6)	C29ⁱⁱ—C30—H30A	43.6
C8—C9—H9	120.0	C28ⁱⁱ—C30—H30A	155.1
C10—C9—H9	120.0	O1ⁱⁱ—C30—H30B	55.3
N2—C10—C9	122.2 (5)	N8—C30—H30B	113.5
N2—C10—H10	118.9	C29ⁱⁱ—C30—H30B	125.5
C9—C10—H10	118.9	C28ⁱⁱ—C30—H30B	82.6
C12—C11—C4	121.8 (5)	H30A—C30—H30B	109.5
C12—C11—H11	119.1	O1ⁱⁱ—C30—H30C	65.8
C4—C11—H11	119.1	N8—C30—H30C	112.3
C11—C12—C7	121.6 (5)	C29ⁱⁱ—C30—H30C	123.5
C11—C12—H12	119.2	C28ⁱⁱ—C30—H30C	85.5
C7—C12—H12	119.2	H30A—C30—H30C	109.5
N3—C13—C14	120.7 (5)	H30B—C30—H30C	109.5

N4—Cu1—N1—C1	−77.5 (4)	C17—N3—C13—C14	0.0 (7)
N2—Cu1—N1—C1	179.5 (4)	Cu1—N3—C13—C14	176.8 (4)
Cl1—Cu1—N1—C1	65.2 (4)	N3—C13—C14—C15	−0.2 (8)
N4—Cu1—N1—C5	104.9 (3)	C13—C14—C15—C16	0.1 (8)
N2—Cu1—N1—C5	1.8 (3)	C14—C15—C16—C17	0.3 (7)
Cl1—Cu1—N1—C5	−112.5 (3)	C14—C15—C16—C23	−178.9 (5)
N1—Cu1—N2—C10	−179.7 (5)	C13—N3—C17—C16	0.4 (7)
N3—Cu1—N2—C10	7.2 (5)	Cu1—N3—C17—C16	−176.8 (3)
N4—Cu1—N2—C10	89.2 (5)	C13—N3—C17—C18	−178.9 (4)
Cl1—Cu1—N2—C10	−91.0 (5)	Cu1—N3—C17—C18	3.9 (5)
N1—Cu1—N2—C6	−2.1 (3)	C15—C16—C17—N3	−0.5 (7)
N3—Cu1—N2—C6	−175.2 (3)	C23—C16—C17—N3	178.8 (4)
N4—Cu1—N2—C6	−93.2 (3)	C15—C16—C17—C18	178.7 (4)
Cl1—Cu1—N2—C6	86.6 (3)	C23—C16—C17—C18	−2.0 (6)
N4—Cu1—N3—C13	178.4 (4)	C22—N4—C18—C19	0.4 (6)
N2—Cu1—N3—C13	−78.8 (4)	Cu1—N4—C18—C19	176.7 (3)
Cl1—Cu1—N3—C13	36.4 (4)	C22—N4—C18—C17	179.7 (4)
N4—Cu1—N3—C17	−4.6 (3)	Cu1—N4—C18—C17	−3.9 (4)
N2—Cu1—N3—C17	98.1 (3)	N3—C17—C18—N4	0.2 (6)
Cl1—Cu1—N3—C17	−146.6 (3)	C16—C17—C18—N4	−179.1 (4)
N1—Cu1—N4—C22	6.1 (4)	N3—C17—C18—C19	179.6 (4)
N3—Cu1—N4—C22	−179.7 (4)	C16—C17—C18—C19	0.3 (6)
N2—Cu1—N4—C22	86.7 (4)	N4—C18—C19—C20	1.2 (6)
Cl1—Cu1—N4—C22	−93.0 (4)	C17—C18—C19—C20	−178.1 (4)
N1—Cu1—N4—C18	−169.6 (3)	N4—C18—C19—C24	180.0 (4)
N3—Cu1—N4—C18	4.6 (3)	C17—C18—C19—C24	0.7 (6)
N2—Cu1—N4—C18	−89.0 (3)	C18—C19—C20—C21	−1.8 (7)
Cl1—Cu1—N4—C18	91.3 (3)	C24—C19—C20—C21	179.5 (4)
C5—N1—C1—C2	−2.7 (7)	C19—C20—C21—C22	0.8 (8)
Cu1—N1—C1—C2	179.7 (4)	C18—N4—C22—C21	−1.5 (7)
N1—C1—C2—C3	4.0 (8)	Cu1—N4—C22—C21	−176.9 (3)
C1—C2—C3—C4	−2.5 (8)	C20—C21—C22—N4	0.9 (8)
C2—C3—C4—C5	0.0 (8)	C15—C16—C23—C24	−177.7 (5)
C2—C3—C4—C11	−180.0 (5)	C17—C16—C23—C24	3.0 (7)
C1—N1—C5—C4	0.0 (6)	C16—C23—C24—C19	−2.2 (8)
Cu1—N1—C5—C4	177.8 (3)	C18—C19—C24—C23	0.3 (7)
C1—N1—C5—C6	−179.2 (4)	C20—C19—C24—C23	179.0 (5)
Cu1—N1—C5—C6	−1.4 (5)	C30ⁱⁱ—O1—C28—N8	3 (2)
C3—C4—C5—N1	1.4 (6)	C30ⁱⁱ—N8—C28—C29ⁱⁱ	178 (3)
C11—C4—C5—N1	−178.7 (4)	C30—N8—C28—C29ⁱⁱ	−2 (3)
C3—C4—C5—C6	−179.5 (4)	C29—N8—C28—C29ⁱⁱ	180.000 (3)
C11—C4—C5—C6	0.4 (6)	C28ⁱⁱ—N8—C28—O1	171 (100)
C10—N2—C6—C7	0.5 (7)	C30ⁱⁱ—N8—C28—O1	−3 (2)
Cu1—N2—C6—C7	−177.5 (3)	C30—N8—C28—O1	177 (2)
C10—N2—C6—C5	180.0 (4)	C29—N8—C28—O1	−1 (4)
Cu1—N2—C6—C5	2.0 (5)	C29ⁱⁱ—N8—C28—O1	179 (4)
N1—C5—C6—N2	−0.6 (6)	C30—N8—C28—C30ⁱⁱ	180.000 (5)
C4—C5—C6—N2	−179.8 (4)	C29—N8—C28—C30ⁱⁱ	2 (3)
N1—C5—C6—C7	178.9 (4)	C29ⁱⁱ—N8—C28—C30ⁱⁱ	−178 (3)
C4—C5—C6—C7	−0.2 (6)	C28—N8—C29—C28ⁱⁱ	180.000 (4)
N2—C6—C7—C8	0.5 (7)	C30ⁱⁱ—N8—C29—C28ⁱⁱ	−177 (3)
C5—C6—C7—C8	−179.0 (4)	C30—N8—C29—C28ⁱⁱ	3 (3)
N2—C6—C7—C12	178.2 (4)	C28ⁱⁱ—N8—C29—C30ⁱⁱ	177 (3)
C5—C6—C7—C12	−1.3 (6)	C28—N8—C29—C30ⁱⁱ	−3 (3)
C6—C7—C8—C9	−1.5 (8)	C30—N8—C29—C30ⁱⁱ	180.000 (4)
C12—C7—C8—C9	−179.0 (5)	C28ⁱⁱ—N8—C30—O1ⁱⁱ	−2.8 (19)
C7—C8—C9—C10	1.4 (9)	C28—N8—C30—O1ⁱⁱ	177.2 (19)
C6—N2—C10—C9	−0.6 (8)	C29—N8—C30—O1ⁱⁱ	−5 (2)
Cu1—N2—C10—C9	176.9 (4)	C29ⁱⁱ—N8—C30—O1ⁱⁱ	175 (2)
C8—C9—C10—N2	−0.4 (9)	C28ⁱⁱ—N8—C30—C29ⁱⁱ	−178 (2)
C3—C4—C11—C12	−179.1 (5)	C28—N8—C30—C29ⁱⁱ	2 (2)
C5—C4—C11—C12	1.0 (7)	C29—N8—C30—C29ⁱⁱ	180.000 (4)
C4—C11—C12—C7	−2.6 (8)	C28—N8—C30—C28ⁱⁱ	180.000 (4)
C8—C7—C12—C11	−179.8 (5)	C29—N8—C30—C28ⁱⁱ	−2 (2)
C6—C7—C12—C11	2.7 (7)	C29ⁱⁱ—N8—C30—C28ⁱⁱ	178 (2)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12···Cl1ⁱⁱⁱ	0.93	2.82	3.701 (6)	159
C23—H23···N6^iv	0.93	2.52	3.425 (7)	163

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

Experimental details

Crystal data
Chemical formula	[CuCl(C₁₂H₈N₂)₂]₂[Fe(CN)₅(NO)]·C₃H₇NO
M_r	1207.85
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	9.9645 (13), 10.6001 (18), 12.623 (2)
α, β, γ (°)	79.585 (14), 84.896 (12), 82.047 (12)
V (Å³)	1295.9 (4)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	1.25
Crystal size (mm)	0.50 × 0.40 × 0.20

Data collection
Diffractometer	Oxford Diffraction Xcalibur 3
Absorption correction	Numerical (CrysAlis PRO; Oxford Diffraction, 2010)
T_min, T_max	0.575, 0.789
No. of measured, independent and observed [I > 2σ(I)] reflections	11289, 5647, 2685
R_int	0.041
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.061, 0.182, 0.99
No. of reflections	5647
No. of parameters	366
No. of restraints	5
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.73, −0.61

Computer programs: CrysAlis PRO (Oxford Diffraction, 2010), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12···Cl1ⁱ	0.93	2.82	3.701 (6)	159
C23—H23···N6ⁱⁱ	0.93	2.52	3.425 (7)	163

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

Acknowledgements

This work was partly supported by the State Fund for Fundamental Researches of Ukraine (project 54.3/005).

References

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Volume 69| Part 7| July 2013| Pages m391-m392

https://doi.org/10.1107/S1600536813015547

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

Bis[chloridobis(1,10-phenanthroline)copper(II)] penta­cyanido­nitro­soferrate(II) di­methyl­formamide monosolvate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

metal-organic compounds

Bis[chloridobis(1,10-phenanthroline)copper(II)] pentacyanidonitrosoferrate(II) dimethylformamide monosolvate