Bis(2,9-dimethyl-1,10-phenanthroline)copper(I) penta­cyanido­nitro­soferrate(II)

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

doi:10.1107/S1600536813031760

metal-organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 69| Part 12| December 2013| Pages m684-m685

doi:10.1107/S1600536813031760

Open

access

Bis(2,9-dimethyl-1,10-phenanthroline)copper(I) pentacyanidonitrosoferrate(II)

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

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

(Received 5 November 2013; accepted 21 November 2013; online 27 November 2013)

The asymmetric unit of the title complex [Cu(C₁₄H₁₂N₂)₂]₂[Fe(CN)₅(NO)], consists of a [Cu(dmp)₂]⁺ cation (dmp is 2,9-dimethyl-1,10-phenanthroline) and half an [Fe(CN)₅(NO)]²⁻ anion. The anion is disordered across an inversion center with the Fe^II ion slightly offset (ca 0.205Å) from the inversion center in the direction of the disordered trans-coordinating CN/NO ligands. The anion has a distorted octahedral coordination geometry. The Cu^I ion is coordinated by two phenanthroline ligands in a distorted tetrahedral geometry. The dihedral angle between the phenanthroline ligands is 77.16 (4) Å. In the crystal, the cations are connected to the anions by weak C—H⋯N hydrogen bonds. In addition, weak π–π stacking interactions are observed, with centroid–centroid distances in the range 3.512 (3)–3.859 (3) Å.

CCDC reference: 712222

Related literature

For background to the direct synthesis of coordination compounds, see: Kokozay & Vassilyeva (2002 ); Nesterova et al. (2008 ). For the direct synthesis of heterometallic Cu-containing complexes, see: Buvaylo et al. (2005 ); Nesterova et al. (2004 , 2005 ); Pryma et al. (2003 ). For the application of anionic complexes in the preparation of heterometallic compounds, see: Nikitina et al. (2008 , 2009 ). For the structures of related complexes, see: Blake et al. (1998 ); Chen et al. (2002 ); Morpurgo et al. (1984 ); Cuttell et al. (2002 ); King et al. (2005 ); Soria et al. (2002 ); Shevyakova et al. (2002 ); Peresypkina & Vostrikova (2012 ).

Experimental

Crystal data

[Cu(C₁₄H₁₂N₂)₂]₂[Fe(CN)₅(NO)]
M_r = 1176.06
Triclinic, $[P \overline 1]$
a = 7.371 (3) Å
b = 13.741 (3) Å
c = 15.065 (4) Å
α = 115.269 (4)°
β = 95.327 (3)°
γ = 101.323 (4)°
V = 1325.9 (7) Å³
Z = 1
Mo Kα radiation
μ = 1.12 mm⁻¹
T = 293 K
0.50 × 0.40 × 0.20 mm

Data collection

Oxford Diffraction Xcalibur3 diffractometer
Absorption correction: numerical (CrysAlis PRO; Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ) T_min = 0.604, T_max = 0.807
8613 measured reflections
5112 independent reflections
3100 reflections with I > 2σ(I)
R_int = 0.048

Refinement

R[F² > 2σ(F²)] = 0.050
wR(F²) = 0.109
S = 0.93
5112 reflections
377 parameters
H-atom parameters constrained
Δρ_max = 0.38 e Å⁻³
Δρ_min = −0.31 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C17—H17⋯N6ⁱ	0.93	2.55	3.393 (6)	151
Symmetry code: (i) -x+2, -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; software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

CCDC reference: 712222

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: 10.1107/S1600536813031760/lh5667sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813031760/lh5667Isup2.hkl

checkCIF report

Comment top

The title compound was obtained as part of our research in the field of direct synthesis of coordination compounds (Buvaylo et al., 2005; Kokozay et al., 2002; Nikitina et al., 2008, 2009; Nesterova et al., 2004, 2005, 2008; Pryma et al.,2003). Complexes of copper chelated with phenanthroline (in particular 2,9-dimethyl-1,10-phenanthroline) have attracted attention due to their longlived excited states and potential use in solar energy conversion (Blake et al., 1998; Chen et al., 2002; Morpurgo et al., 1984; Cuttell et al., 2002; King et al., 2005).

In this paper we present a novel Cu/Fe heterometallic ionic complex [Cu(dmp)₂]₂[Fe(CN)₅NO] which consists of discrete [Cu(dmp)₂]⁺ and [Fe(CN)₅NO]^2- ions (Fig. 1). The Cu^I ion adopts a distorted tetrahedral environment by coordinating with four nitrogen atoms from two dmp ligands. The dihedral angle between the two dmp ligands (77.16 (4) Å) as well as the range of Cu—N bond distances of 2.034 (3) - 2.079 (3) Å is in good agreement with the previously reported values for analagous complexes (King et al., 2005 and references therein). The nitroprusside anion lies on an inversion centre and disordered over two positions so that iron atom occupies two very close positions (Fe···Fe distance is 0.410 (15) Å) corresponding to the coordination of two disordered CN and NO groups in the axial sites with very close positions. However, geometric parameters (average Fe—CN and Fe—NO bond distances of 1.96 Å and 1.63 Å respectively) are in a good agreement with literature values (Soria et al. (2002); Shevyakova et al. (2002); Peresypkina et al. (2012).

In the crystal, cations are connected to the anions by weak C—H···N hydrogen bonds. In addition weak π–π stacking interactions with centroid–centroid distances in the range 3.512 (3)–3.859 (3)° are observed (Fig. 2).

Related literature top

For background to the direct synthesis of coordination compounds, see: Kokozay & Vassilyeva (2002); Nesterova et al. (2008). For the direct synthesis of heterometallic Cu-containing complexes, see: Buvaylo et al. (2005); Nesterova et al. (2004, 2005); Pryma et al. (2003). For the application of anionic complexes in the preparation of heterometallic compounds, see: Nikitina et al. (2008, 2009). For the structures of related complexes, see: Blake et al. (1998); Chen et al. (2002); Morpurgo et al. (1984); Cuttell et al. (2002); King et al. (2005); Soria et al. (2002); Shevyakova et al. (2002); Peresypkina & Vostrikova (2012).

Experimental top

Copper powder (0.04 g, 0.63 mmol), NH₄Br (0.123 g, 1.25 mmol), Na₂[Fe(CN)₅(NO)]^.2H₂O (0.188 g, 0.63 mmol) and dmp (0.262 g, 1.26 mmol) in DMF (30 ml) were heated to 333–343 K and stirred magnetically until total dissolution of copper was observed (2.5 h). Red needle-shaped crystals suitable for X-ray crystallography was isolated from the resulting dark-red solution with addition of 2-propanol and diethyl ether in a few days. The crystals (0.1 g, yield 30%) were filtered off, washed with dry methanol, and finally dried in vacuo at room temperature.

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); 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 30% probability level. Symmetry code (A); 2 -x,1-y,-z. The disorder is not shown.
	Fig. 2. Part of the crystal structure with weak hydrogen bonds shown as dashed lines.

Bis(2,9-dimethyl-1,10-phenanthroline)copper(I) pentacyanidonitrosoferrate(II) top

Crystal data top

[Cu(C₁₄H₁₂N₂)₂]₂[Fe(CN)₅(NO)]	Z = 1
M_r = 1176.06	F(000) = 604
Triclinic, P1	D_x = 1.473 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.371 (3) Å	Cell parameters from 4215 reflections
b = 13.741 (3) Å	θ = 2.7–24.8°
c = 15.065 (4) Å	µ = 1.12 mm⁻¹
α = 115.269 (4)°	T = 293 K
β = 95.327 (3)°	Needle-shaped, red
γ = 101.323 (4)°	0.50 × 0.40 × 0.20 mm
V = 1325.9 (7) Å³

Data collection top

Oxford Diffraction Xcalibur3 diffractometer	5112 independent reflections
Radiation source: Enhance (Mo) X-ray Source	3100 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.048
Detector resolution: 16.1827 pixels mm^-1	θ_max = 26.0°, θ_min = 2.9°
ω–scans	h = −8→9
Absorption correction: numerical (CrysAlis PRO; Oxford Diffraction, 2010)	k = −16→16
T_min = 0.604, T_max = 0.807	l = −18→15
8613 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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.109	H-atom parameters constrained
S = 0.93	w = 1/[σ²(F_o²) + (0.0468P)²] where P = (F_o² + 2F_c²)/3
5112 reflections	(Δ/σ)_max = 0.001
377 parameters	Δρ_max = 0.38 e Å⁻³
0 restraints	Δρ_min = −0.31 e Å⁻³

Crystal data top

[Cu(C₁₄H₁₂N₂)₂]₂[Fe(CN)₅(NO)]	γ = 101.323 (4)°
M_r = 1176.06	V = 1325.9 (7) Å³
Triclinic, P1	Z = 1
a = 7.371 (3) Å	Mo Kα radiation
b = 13.741 (3) Å	µ = 1.12 mm⁻¹
c = 15.065 (4) Å	T = 293 K
α = 115.269 (4)°	0.50 × 0.40 × 0.20 mm
β = 95.327 (3)°

Data collection top

Oxford Diffraction Xcalibur3 diffractometer	5112 independent reflections
Absorption correction: numerical (CrysAlis PRO; Oxford Diffraction, 2010)	3100 reflections with I > 2σ(I)
T_min = 0.604, T_max = 0.807	R_int = 0.048
8613 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.050	0 restraints
wR(F²) = 0.109	H-atom parameters constrained
S = 0.93	Δρ_max = 0.38 e Å⁻³
5112 reflections	Δρ_min = −0.31 e Å⁻³
377 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	0.24477 (7)	0.18237 (4)	0.30785 (3)	0.04709 (18)
Fe1	0.9747 (13)	0.5030 (13)	0.0033 (11)	0.0423 (14)	0.50
N1	0.3564 (4)	0.2540 (2)	0.2232 (2)	0.0377 (7)
N2	0.1731 (4)	0.0423 (2)	0.1741 (2)	0.0369 (7)
N3	0.3933 (4)	0.1682 (2)	0.4241 (2)	0.0379 (7)
N4	0.1040 (4)	0.2617 (2)	0.4159 (2)	0.0377 (7)
C1	0.4355 (5)	0.3608 (3)	0.2474 (3)	0.0464 (10)
C2	0.5081 (5)	0.3909 (3)	0.1771 (3)	0.0551 (11)
H2	0.5610	0.4656	0.1954	0.066*
C3	0.5025 (5)	0.3129 (4)	0.0833 (3)	0.0542 (11)
H3	0.5561	0.3335	0.0383	0.065*
C4	0.4148 (5)	0.2001 (3)	0.0542 (3)	0.0407 (9)
C5	0.3423 (4)	0.1751 (3)	0.1269 (3)	0.0345 (8)
C6	0.2450 (4)	0.0621 (3)	0.1008 (3)	0.0336 (8)
C7	0.2248 (5)	−0.0217 (3)	0.0027 (3)	0.0381 (9)
C8	0.3039 (5)	0.0072 (4)	−0.0683 (3)	0.0481 (10)
H8	0.2923	−0.0483	−0.1331	0.058*
C9	0.3950 (5)	0.1129 (4)	−0.0439 (3)	0.0492 (10)
H9	0.4457	0.1292	−0.0918	0.059*
C10	0.1271 (5)	−0.1296 (3)	−0.0187 (3)	0.0458 (10)
H10	0.1092	−0.1876	−0.0829	0.055*
C11	0.0583 (5)	−0.1498 (3)	0.0538 (3)	0.0460 (10)
H11	−0.0052	−0.2220	0.0394	0.055*
C12	0.0824 (5)	−0.0622 (3)	0.1510 (3)	0.0383 (9)
C13	0.4435 (6)	0.4460 (3)	0.3521 (3)	0.0654 (12)
H13A	0.5696	0.4934	0.3804	0.098*
H13B	0.4081	0.4091	0.3919	0.098*
H13C	0.3580	0.4902	0.3512	0.098*
C14	0.0096 (6)	−0.0831 (3)	0.2332 (3)	0.0559 (11)
H14A	0.0870	−0.1209	0.2545	0.084*
H14B	−0.1182	−0.1286	0.2086	0.084*
H14C	0.0137	−0.0133	0.2888	0.084*
C15	0.5321 (5)	0.1207 (3)	0.4270 (3)	0.0454 (10)
C16	0.6193 (6)	0.1264 (3)	0.5157 (3)	0.0547 (11)
H16	0.7197	0.0947	0.5157	0.066*
C17	0.5581 (6)	0.1786 (3)	0.6032 (3)	0.0549 (11)
H17	0.6176	0.1830	0.6625	0.066*
C18	0.4051 (5)	0.2251 (3)	0.6023 (3)	0.0451 (10)
C19	0.3273 (5)	0.2190 (3)	0.5108 (3)	0.0394 (9)
C20	0.1730 (5)	0.2687 (3)	0.5074 (3)	0.0358 (9)
C21	0.1046 (5)	0.3217 (3)	0.5935 (3)	0.0420 (9)
C22	0.1808 (6)	0.3230 (3)	0.6840 (3)	0.0528 (11)
H22	0.1298	0.3551	0.7405	0.063*
C23	0.3275 (6)	0.2779 (3)	0.6893 (3)	0.0548 (11)
H23	0.3780	0.2813	0.7498	0.066*
C24	−0.0412 (6)	0.3721 (3)	0.5857 (3)	0.0516 (11)
H24	−0.0922	0.4082	0.6412	0.062*
C25	−0.1066 (6)	0.3674 (3)	0.4963 (3)	0.0516 (10)
H25	−0.2005	0.4022	0.4912	0.062*
C26	−0.0338 (5)	0.3106 (3)	0.4117 (3)	0.0417 (9)
C27	0.5909 (6)	0.0609 (4)	0.3308 (3)	0.0619 (12)
H27A	0.5252	−0.0168	0.3005	0.093*
H27B	0.7245	0.0690	0.3432	0.093*
H27C	0.5611	0.0917	0.2866	0.093*
C28	−0.1065 (6)	0.3050 (4)	0.3126 (3)	0.0544 (11)
H28A	−0.0458	0.2601	0.2627	0.082*
H28B	−0.0798	0.3788	0.3182	0.082*
H28C	−0.2404	0.2723	0.2937	0.082*
C29	1.0149 (5)	0.4533 (3)	0.1060 (3)	0.0446 (9)
N5	1.0271 (5)	0.4286 (3)	0.1677 (3)	0.0631 (10)
C30	1.1809 (6)	0.6397 (3)	0.0926 (3)	0.0440 (9)
N6	1.2879 (5)	0.7213 (3)	0.1470 (3)	0.0626 (10)
C31	0.812 (5)	0.559 (2)	0.036 (2)	0.070 (5)	0.50
N7	0.681 (4)	0.603 (2)	0.0546 (17)	0.070 (5)	0.50
N8	0.805 (3)	0.5579 (11)	0.0446 (12)	0.026 (3)	0.50
O1	0.688 (3)	0.5921 (16)	0.0752 (11)	0.055 (3)	0.50

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.0659 (3)	0.0491 (3)	0.0278 (3)	0.0167 (2)	0.0157 (2)	0.0169 (2)
Fe1	0.057 (4)	0.0453 (14)	0.0274 (15)	0.012 (3)	0.009 (3)	0.0199 (12)
N1	0.0449 (17)	0.0362 (18)	0.0314 (17)	0.0069 (14)	0.0073 (14)	0.0166 (14)
N2	0.0400 (16)	0.0401 (18)	0.0323 (17)	0.0114 (14)	0.0067 (14)	0.0176 (14)
N3	0.0423 (16)	0.0398 (18)	0.0323 (17)	0.0120 (15)	0.0089 (15)	0.0162 (14)
N4	0.0433 (17)	0.0362 (17)	0.0302 (17)	0.0064 (14)	0.0041 (15)	0.0143 (14)
C1	0.047 (2)	0.045 (2)	0.045 (2)	0.0067 (19)	0.006 (2)	0.0210 (19)
C2	0.059 (2)	0.046 (3)	0.064 (3)	0.005 (2)	0.015 (2)	0.032 (2)
C3	0.056 (2)	0.065 (3)	0.053 (3)	0.009 (2)	0.019 (2)	0.038 (2)
C4	0.0384 (19)	0.057 (3)	0.034 (2)	0.0162 (19)	0.0086 (18)	0.0255 (19)
C5	0.0341 (18)	0.043 (2)	0.0300 (19)	0.0145 (17)	0.0068 (16)	0.0184 (17)
C6	0.0358 (18)	0.040 (2)	0.0295 (19)	0.0158 (17)	0.0084 (17)	0.0175 (16)
C7	0.0377 (19)	0.048 (2)	0.030 (2)	0.0209 (18)	0.0048 (17)	0.0153 (17)
C8	0.050 (2)	0.063 (3)	0.027 (2)	0.017 (2)	0.0100 (19)	0.0155 (19)
C9	0.046 (2)	0.080 (3)	0.031 (2)	0.022 (2)	0.0159 (19)	0.030 (2)
C10	0.047 (2)	0.048 (3)	0.036 (2)	0.020 (2)	0.0036 (19)	0.0117 (19)
C11	0.045 (2)	0.037 (2)	0.053 (3)	0.0118 (18)	0.004 (2)	0.017 (2)
C12	0.042 (2)	0.039 (2)	0.039 (2)	0.0130 (18)	0.0068 (18)	0.0210 (18)
C13	0.081 (3)	0.043 (3)	0.058 (3)	0.010 (2)	0.013 (3)	0.013 (2)
C14	0.067 (3)	0.048 (3)	0.061 (3)	0.015 (2)	0.022 (2)	0.031 (2)
C15	0.049 (2)	0.045 (2)	0.042 (2)	0.005 (2)	0.001 (2)	0.024 (2)
C16	0.054 (2)	0.055 (3)	0.058 (3)	0.017 (2)	0.003 (2)	0.029 (2)
C17	0.067 (3)	0.055 (3)	0.041 (3)	0.008 (2)	−0.005 (2)	0.027 (2)
C18	0.058 (2)	0.041 (2)	0.033 (2)	0.006 (2)	0.004 (2)	0.0179 (18)
C19	0.052 (2)	0.034 (2)	0.029 (2)	0.0044 (18)	0.0058 (18)	0.0152 (16)
C20	0.047 (2)	0.033 (2)	0.0260 (19)	0.0058 (17)	0.0075 (18)	0.0142 (16)
C21	0.053 (2)	0.039 (2)	0.031 (2)	0.0065 (19)	0.0102 (19)	0.0147 (17)
C22	0.072 (3)	0.054 (3)	0.026 (2)	0.009 (2)	0.014 (2)	0.0142 (19)
C23	0.080 (3)	0.053 (3)	0.026 (2)	0.009 (2)	0.006 (2)	0.0180 (19)
C24	0.064 (3)	0.050 (3)	0.035 (2)	0.013 (2)	0.022 (2)	0.0115 (19)
C25	0.058 (2)	0.050 (3)	0.050 (3)	0.023 (2)	0.017 (2)	0.020 (2)
C26	0.046 (2)	0.040 (2)	0.039 (2)	0.0096 (19)	0.0086 (19)	0.0193 (18)
C27	0.067 (3)	0.070 (3)	0.060 (3)	0.031 (2)	0.027 (2)	0.032 (2)
C28	0.062 (2)	0.065 (3)	0.041 (2)	0.024 (2)	0.009 (2)	0.026 (2)
C29	0.055 (2)	0.045 (2)	0.037 (2)	0.0171 (19)	0.015 (2)	0.0185 (19)
N5	0.093 (3)	0.067 (3)	0.044 (2)	0.028 (2)	0.020 (2)	0.0347 (19)
C30	0.058 (2)	0.048 (3)	0.033 (2)	0.021 (2)	0.009 (2)	0.0222 (19)
N6	0.069 (2)	0.062 (3)	0.052 (2)	0.016 (2)	−0.003 (2)	0.025 (2)
C31	0.087 (9)	0.109 (9)	0.050 (8)	0.044 (7)	0.017 (7)	0.061 (7)
N7	0.087 (9)	0.109 (9)	0.050 (8)	0.044 (7)	0.017 (7)	0.061 (7)
N8	0.039 (5)	0.022 (4)	0.011 (5)	0.012 (4)	0.009 (4)	−0.001 (4)
O1	0.082 (6)	0.087 (7)	0.027 (5)	0.057 (5)	0.026 (5)	0.036 (5)

Geometric parameters (Å, º) top

Cu1—N2	2.034 (3)	C13—H13A	0.9600
Cu1—N4	2.039 (3)	C13—H13B	0.9600
Cu1—N1	2.053 (3)	C13—H13C	0.9600
Cu1—N3	2.079 (3)	C14—H14A	0.9600
Fe1—Fe1ⁱ	0.410 (15)	C14—H14B	0.9600
Fe1—C31	1.56 (4)	C14—H14C	0.9600
Fe1—N8	1.625 (19)	C15—C16	1.392 (5)
Fe1—C30ⁱ	1.908 (15)	C15—C27	1.484 (5)
Fe1—C31ⁱ	1.96 (4)	C16—C17	1.373 (6)
Fe1—C29	1.961 (16)	C16—H16	0.9300
Fe1—C29ⁱ	1.981 (16)	C17—C18	1.403 (5)
Fe1—C30	1.998 (15)	C17—H17	0.9300
Fe1—N8ⁱ	2.03 (2)	C18—C19	1.404 (5)
N1—C1	1.341 (4)	C18—C23	1.435 (5)
N1—C5	1.370 (4)	C19—C20	1.446 (5)
N2—C12	1.334 (4)	C20—C21	1.388 (5)
N2—C6	1.372 (4)	C21—C24	1.410 (5)
N3—C15	1.324 (5)	C21—C22	1.416 (5)
N3—C19	1.379 (4)	C22—C23	1.360 (6)
N4—C26	1.334 (4)	C22—H22	0.9300
N4—C20	1.380 (4)	C23—H23	0.9300
C1—C2	1.404 (5)	C24—C25	1.358 (5)
C1—C13	1.497 (5)	C24—H24	0.9300
C2—C3	1.351 (5)	C25—C26	1.401 (5)
C2—H2	0.9300	C25—H25	0.9300
C3—C4	1.409 (5)	C26—C28	1.502 (5)
C3—H3	0.9300	C27—H27A	0.9600
C4—C5	1.399 (5)	C27—H27B	0.9600
C4—C9	1.421 (5)	C27—H27C	0.9600
C5—C6	1.439 (5)	C28—H28A	0.9600
C6—C7	1.403 (5)	C28—H28B	0.9600
C7—C10	1.397 (5)	C28—H28C	0.9600
C7—C8	1.425 (5)	C29—N5	1.120 (4)
C8—C9	1.346 (5)	C29—Fe1ⁱ	1.981 (16)
C8—H8	0.9300	C30—N6	1.140 (5)
C9—H9	0.9300	C30—Fe1ⁱ	1.908 (15)
C10—C11	1.354 (5)	C31—N7	1.23 (5)
C10—H10	0.9300	C31—Fe1ⁱ	1.96 (4)
C11—C12	1.410 (5)	N8—O1	1.11 (3)
C11—H11	0.9300	N8—Fe1ⁱ	2.03 (2)
C12—C14	1.507 (5)

N2—Cu1—N4	135.31 (11)	C8—C9—H9	119.6
N2—Cu1—N1	82.52 (12)	C4—C9—H9	119.6
N4—Cu1—N1	121.22 (12)	C11—C10—C7	120.1 (4)
N2—Cu1—N3	114.85 (12)	C11—C10—H10	120.0
N4—Cu1—N3	82.49 (12)	C7—C10—H10	120.0
N1—Cu1—N3	126.67 (11)	C10—C11—C12	120.4 (4)
Fe1ⁱ—Fe1—C31	165 (5)	C10—C11—H11	119.8
Fe1ⁱ—Fe1—N8	166 (5)	C12—C11—H11	119.8
C31—Fe1—N8	4.6 (19)	N2—C12—C11	121.3 (3)
Fe1ⁱ—Fe1—C30ⁱ	97 (4)	N2—C12—C14	117.4 (3)
C31—Fe1—C30ⁱ	96.8 (11)	C11—C12—C14	121.3 (3)
N8—Fe1—C30ⁱ	96.8 (7)	C1—C13—H13A	109.5
Fe1ⁱ—Fe1—C31ⁱ	12 (4)	C1—C13—H13B	109.5
C31—Fe1—C31ⁱ	176.8 (10)	H13A—C13—H13B	109.5
N8—Fe1—C31ⁱ	175.8 (18)	C1—C13—H13C	109.5
C30ⁱ—Fe1—C31ⁱ	86.0 (10)	H13A—C13—H13C	109.5
Fe1ⁱ—Fe1—C29	87 (4)	H13B—C13—H13C	109.5
C31—Fe1—C29	99.8 (13)	C12—C14—H14A	109.5
N8—Fe1—C29	95.2 (10)	C12—C14—H14B	109.5
C30ⁱ—Fe1—C29	93.0 (7)	H14A—C14—H14B	109.5
C31ⁱ—Fe1—C29	81.6 (11)	C12—C14—H14C	109.5
Fe1ⁱ—Fe1—C29ⁱ	81 (4)	H14A—C14—H14C	109.5
C31—Fe1—C29ⁱ	91.8 (14)	H14B—C14—H14C	109.5
N8—Fe1—C29ⁱ	96.4 (10)	N3—C15—C16	121.8 (4)
C30ⁱ—Fe1—C29ⁱ	88.4 (6)	N3—C15—C27	116.8 (3)
C31ⁱ—Fe1—C29ⁱ	86.7 (11)	C16—C15—C27	121.3 (4)
C29—Fe1—C29ⁱ	168.1 (5)	C17—C16—C15	120.5 (4)
Fe1ⁱ—Fe1—C30	72 (4)	C17—C16—H16	119.8
C31—Fe1—C30	94.9 (12)	C15—C16—H16	119.8
N8—Fe1—C30	94.9 (9)	C16—C17—C18	119.5 (4)
C30ⁱ—Fe1—C30	168.2 (5)	C16—C17—H17	120.3
C31ⁱ—Fe1—C30	82.3 (9)	C18—C17—H17	120.3
C29—Fe1—C30	86.5 (6)	C17—C18—C19	117.0 (3)
C29ⁱ—Fe1—C30	89.7 (6)	C17—C18—C23	123.4 (4)
Fe1ⁱ—Fe1—N8ⁱ	11 (4)	C19—C18—C23	119.6 (4)
C31—Fe1—N8ⁱ	174.2 (19)	N3—C19—C18	122.7 (3)
N8—Fe1—N8ⁱ	177.2 (10)	N3—C19—C20	118.5 (3)
C30ⁱ—Fe1—N8ⁱ	85.9 (6)	C18—C19—C20	118.8 (3)
C31ⁱ—Fe1—N8ⁱ	3.6 (15)	N4—C20—C21	123.7 (3)
C29—Fe1—N8ⁱ	85.2 (8)	N4—C20—C19	116.3 (3)
C29ⁱ—Fe1—N8ⁱ	83.1 (7)	C21—C20—C19	120.1 (3)
C30—Fe1—N8ⁱ	82.4 (5)	C20—C21—C24	117.1 (4)
C1—N1—C5	118.1 (3)	C20—C21—C22	120.0 (4)
C1—N1—Cu1	130.8 (2)	C24—C21—C22	122.9 (4)
C5—N1—Cu1	111.1 (2)	C23—C22—C21	120.9 (4)
C12—N2—C6	118.1 (3)	C23—C22—H22	119.6
C12—N2—Cu1	130.3 (2)	C21—C22—H22	119.6
C6—N2—Cu1	111.5 (2)	C22—C23—C18	120.6 (4)
C15—N3—C19	118.5 (3)	C22—C23—H23	119.7
C15—N3—Cu1	131.4 (3)	C18—C23—H23	119.7
C19—N3—Cu1	110.1 (2)	C25—C24—C21	119.4 (4)
C26—N4—C20	117.4 (3)	C25—C24—H24	120.3
C26—N4—Cu1	130.0 (2)	C21—C24—H24	120.3
C20—N4—Cu1	112.6 (2)	C24—C25—C26	120.5 (4)
N1—C1—C2	121.0 (4)	C24—C25—H25	119.7
N1—C1—C13	117.3 (3)	C26—C25—H25	119.7
C2—C1—C13	121.7 (4)	N4—C26—C25	121.9 (4)
C3—C2—C1	121.1 (4)	N4—C26—C28	117.5 (3)
C3—C2—H2	119.5	C25—C26—C28	120.6 (4)
C1—C2—H2	119.5	C15—C27—H27A	109.5
C2—C3—C4	119.4 (4)	C15—C27—H27B	109.5
C2—C3—H3	120.3	H27A—C27—H27B	109.5
C4—C3—H3	120.3	C15—C27—H27C	109.5
C5—C4—C3	117.0 (3)	H27A—C27—H27C	109.5
C5—C4—C9	119.5 (4)	H27B—C27—H27C	109.5
C3—C4—C9	123.5 (4)	C26—C28—H28A	109.5
N1—C5—C4	123.2 (3)	C26—C28—H28B	109.5
N1—C5—C6	117.1 (3)	H28A—C28—H28B	109.5
C4—C5—C6	119.7 (3)	C26—C28—H28C	109.5
N2—C6—C7	123.2 (3)	H28A—C28—H28C	109.5
N2—C6—C5	117.4 (3)	H28B—C28—H28C	109.5
C7—C6—C5	119.4 (3)	N5—C29—Fe1	174.5 (4)
C10—C7—C6	116.9 (3)	N5—C29—Fe1ⁱ	173.2 (5)
C10—C7—C8	124.0 (3)	N6—C30—Fe1ⁱ	173.6 (4)
C6—C7—C8	119.0 (3)	N6—C30—Fe1	174.6 (4)
C9—C8—C7	121.6 (4)	N7—C31—Fe1	175 (3)
C9—C8—H8	119.2	N7—C31—Fe1ⁱ	173 (3)
C7—C8—H8	119.2	O1—N8—Fe1	176.5 (19)
C8—C9—C4	120.8 (4)	O1—N8—Fe1ⁱ	176.7 (16)

Symmetry code: (i) −x+2, −y+1, −z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C17—H17···N6ⁱⁱ	0.93	2.55	3.393 (6)	151

Symmetry code: (ii) −x+2, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C17—H17···N6ⁱ	0.93	2.55	3.393 (6)	151.2

Symmetry code: (i) −x+2, −y+1, −z+1.

Acknowledgements

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

References

Blake, A. J., Hill, S. J., Hubberstey, P. & Li, W. S. (1998). J. Chem. Soc. Dalton Trans. pp. 909–915. Web of Science CSD CrossRef Google Scholar
Buvaylo, E. A., Kokozay, V. N., Vassilyeva, O. Yu., Skelton, B. W., Jezierska, J., Brunel, L. C. & Ozarowski, A. (2005). Chem. Commun. pp. 4976–4978. Web of Science CSD CrossRef Google Scholar
Chen, L. X., Jenning, G., Liu, T., Gosztola, D. J., Hessler, J. P., Scaltrito, D. V. & Meyers, G. J. (2002). J. Am. Chem. Soc. 124, 10861–10867. Web of Science CrossRef PubMed CAS Google Scholar
Cuttell, D. G., Kuang, S. M., Fanwick, P. E., McMillin, D. R. & Walton, R. A. (2002). J. Am. Chem. Soc. 124, 6–7. Web of Science CSD CrossRef PubMed CAS Google Scholar
King, G., Gembicky, M. & Coppens, P. (2005). Acta Cryst. C61, m329–m332. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Kokozay, V. N. & Vassilyeva, O. Yu. (2002). Transition Met. Chem. 27, 693–699. Web of Science CrossRef CAS Google Scholar
Morpurgo, G., Dessy, G. & Fares, V. (1984). J. Chem. Soc. Dalton Trans. pp. 785–791. CSD CrossRef Web of Science Google Scholar
Nesterova, O. V., Lipetskaya, A. V., Petrusenko, S. R., Kokozay, V. N., Skelton, B. W. & Jezierska, J. (2005). Polyhedron, 24, 1425–1434. Web of Science CSD CrossRef CAS Google Scholar
Nesterova, O. V., Petrusenko, S. R., Kokozay, V. N., Skelton, B. W., Jezierska, J., Linert, W. & Ozarowski, A. (2008). Dalton Trans. pp. 1431–1436. Web of Science CSD CrossRef Google Scholar
Nesterova (Pryma), O. V., Petrusenko, S. R., Kokozay, V. N., Skelton, B. W. & Linert, W. (2004). Inorg. Chem. Commun. 7, 450–454. Google Scholar
Nikitina, V. M., Nesterova, O. V., Kokozay, V. N., Dyakonenko, V. V., Shishkin, O. V. & Jezierska, J. (2009). Inorg. Chem. Commun. 12, 101–104. Web of Science CSD CrossRef CAS Google Scholar
Nikitina, V. M., Nesterova, O. V., Kokozay, V. N., Goreshnik, E. A. & Jezierska, J. (2008). Polyhedron, 27, 2426–2430. Web of Science CSD CrossRef CAS Google Scholar
Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England. Google Scholar
Peresypkina, E. V. & Vostrikova, K. E. (2012). Dalton Trans. 41, 4100–4106. Web of Science CSD CrossRef CAS PubMed Google Scholar
Pryma, O. V., Petrusenko, S. R., Kokozay, V. N., Skelton, B. W., Shishkin, O. V. & Teplytska, T. S. (2003). Eur. J. Inorg. Chem. pp. 1426–1432. CSD CrossRef Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Shevyakova, I. Yu., Buravov, L. I., Kushch, L. A., Yagubskii, E. B., Khasanov, S. S., Zorina, L. V., Shibaeva, R. P., Drichko, N. V. & Olejniczak, I. (2002). Russ. J. Coord. Chem. 28, 520–529. Web of Science CrossRef Google Scholar
Soria, D. B., Villalba, M. E. C., Piro, O. E. & Aymonino, P. J. (2002). Polyhedron, 21, 1767–1774. Web of Science CSD CrossRef CAS Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 69| Part 12| December 2013| Pages m684-m685

doi:10.1107/S1600536813031760

Open

access

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

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

Bis(2,9-di­methyl-1,10-phenanthroline)copper(I) penta­cyanido­nitro­soferrate(II)

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

metal-organic compounds

Bis(2,9-dimethyl-1,10-phenanthroline)copper(I) pentacyanidonitrosoferrate(II)