Tris(2,2′-bipyridine)­copper(II) penta­cyanido­nitro­soferrate(II) methanol disolvate monohydrate

Rusanova, J.A.; Nesterova, O.V.; Zubatyuk, R.I.; Kozachuk, O.V.

doi:10.1107/S1600536813006867

metal-organic compounds

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ISSN: 2056-9890

Volume 69| Part 4| April 2013| Pages m212-m213

doi:10.1107/S1600536813006867

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Tris(2,2′-bipyridine)copper(II) pentacyanidonitrosoferrate(II) methanol disolvate monohydrate

Julia A. Rusanova,^a Oksana V. Nesterova,^a Roman I. Zubatyuk ^b and Olesia V. Kozachuk ^a ^*

^aDepartment of Inorganic Chemistry, Taras Shevchenko National University of Kyiv, 64/13 Volodymyrska St, Kyiv 01601, 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 27 February 2013; accepted 12 March 2013; online 16 March 2013)

The title complex [Cu(C₁₀H₈N₂)₃][Fe(CN)₅(NO)]·2CH₃OH·H₂O, consists of discrete [Cu(bpy)₃]²⁺ cations (bpy is 2,2′-bipyridine), [Fe(CN)₅NO]²⁻ anions and solvent molecules of crystallization (two methanol molecules and one water molecules per asymmetric unit). The Cu^II ion adopts a distorted octahedral environment, coordinated by six N atoms from three bpy ligands. The cation charge is balanced by a nitroprusside counter-anion, which has a slightly distorted octahedral coordination geometry. In the crystal, anions and solvent molecules are involved in O—H⋯N and O—H⋯O hydrogen bonds, which form chains along [100]. The cations are located between these chains.

Related literature

For background to the direct synthesis of coordination compounds, see: Buvaylo et al. (2005 ); Babich et al. (1996 ); Kovbasyuk et al. (1998 ); Makhankova et al. (2002 ); Nesterov et al. (2006 ); Pryma et al. (2003 ); Vinogradova et al. (2002 ). For the structures of related complexes, see: Nikitina et al. (2008 ); Vreshch et al. (2009a ,b ); Shyu et al. (1997 ); Shyu & Wei (1999 ); Dong et al. (2003 ); Wang et al. (2007 ); Zhang et al. (2004 ).

Experimental

Crystal data

[Cu(C₁₀H₈N₂)₃][Fe(CN)₅(NO)]·2CH₄O·H₂O
M_r = 830.15
Monoclinic, P 2₁ /c
a = 11.1308 (8) Å
b = 14.7928 (9) Å
c = 23.1448 (17) Å
β = 90.916 (8)°
V = 3810.4 (5) Å³
Z = 4
Mo Kα radiation
μ = 1.00 mm⁻¹
T = 293 K
0.30 × 0.20 × 0.10 mm

Data collection

Oxford Diffraction Xcalibur Sapphire3 diffractometer
Absorption correction: numerical (CrysAlis PRO; Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ) T_min = 0.74, T_max = 0.91
22593 measured reflections
7368 independent reflections
3799 reflections with I > 2σ(I)
R_int = 0.053

Refinement

R[F² > 2σ(F²)] = 0.051
wR(F²) = 0.110
S = 1.01
7368 reflections
496 parameters
H-atom parameters constrained
Δρ_max = 0.59 e Å⁻³
Δρ_min = −0.63 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3S—H3SB⋯N9	0.85	2.04	2.870 (5)	165
O3S—H3SA⋯N7ⁱ	0.85	2.25	3.058 (5)	158
O1S—H1S⋯N8ⁱⁱ	0.82	2.08	2.831 (5)	151
O2S—H2S⋯O3Sⁱⁱⁱ	0.82	1.96	2.746 (7)	161
Symmetry codes: (i) x+1, y, z; (ii) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) $[x-1, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ .

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

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536813006867/lh5592sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813006867/lh5592Isup2.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; Babich et al., 1996; Kovbasyuk et al., 1998; Makhankova et al., 2002; Nesterov et al., 2006; Pryma et al., 2003; Vinogradova et al., 2002). We have shown recently the possibility of using anionic complexes as a source of metalloligands in direct synthesis of heterometallic compounds (Nikitina et al., 2008; Vreshch et al., 2009a,b).

In this paper we present a novel Cu/Fe heterometallic ionic complex [Cu(bpy)₃][Fe(CN)₅NO]^.2CH₃OH^.H₂O which consists of discrete [Cu(bpy)₃]²⁺ and [Fe(CN)₅NO]^2- ions (Fig. 1). The Cu^II ion adopts a distorted octahedral environment by coordinating with six nitrogen atoms from three bpy ligands. The range of Cu—N bond distances of 1.999 (3) - 2.035 (3)Å is in good agreement with the previously reported values for analagous complexes (Shyu et al., 1999; Wang et al., 2007). The anion geometry is unremarkable and in good agreement with reported values for other nitroprussides (Shyu et al. 1997; 1999; Dong et al. 2003; Zhang et al., 2004). In the crystal, anions are involved in the formation of O—H···O hydrogen bonds with solvent molecules to form one-dimensional chains along [100] (Fig. 2). The complex cations are located between these chains.

Related literature top

For background to the direct synthesis of coordination compounds, see: Buvaylo et al. (2005); Babich et al. (1996); Kovbasyuk et al. (1998); Makhankova et al. (2002); Nesterov et al. (2006); Pryma et al. (2003); Vinogradova et al. (2002). For the structures of related complexes, see: Nikitina et al. (2008); Vreshch et al., (2009a,b); Shyu et al. (1997); Shyu & Wei (1999); Dong et al. (2003); Wang et al. (2007); Zhang et al. (2004).

Experimental top

Copper powder (0.04 g, 0.63 mmol), NH₄HSO₄ (0.145 g, 1.26 mmol), Na₂[Fe(CN)₅(NO)]^.2H₂O (0.188 g, 0.63 mmol) and bpy (0.296 g, 1.89 mmol) in methanol (30 ml) were heated to 323-333K and stirred magnetically until total dissolution of copper was observed (30 min). Dark-red crystals suitable for X-ray crystallography was isolated from the resulting dark-red solution with addition of 2-propanol in six 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. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. Part of the crystal structure of the title compound with cations omitted for clarity to show the one-dimensional hydrogen-bonded (dashed lines) chains formed by the anions and solvent molecules.

Tris(2,2'-bipyridine)copper(II) pentacyanidonitrosoferrate(II) methanol disolvate monohydrate top

Crystal data top

[Cu(C₁₀H₈N₂)₃][Fe(CN)₅(NO)]·2CH₄O·H₂O	F(000) = 1708
M_r = 830.15	D_x = 1.447 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5205 reflections
a = 11.1308 (8) Å	θ = 2.6–32.2°
b = 14.7928 (9) Å	µ = 1.00 mm⁻¹
c = 23.1448 (17) Å	T = 293 K
β = 90.916 (8)°	Block, dark red
V = 3810.4 (5) Å³	0.30 × 0.20 × 0.10 mm
Z = 4

Data collection top

Oxford Diffraction Xcalibur Sapphire3 diffractometer	7368 independent reflections
Radiation source: fine-focus sealed tube	3799 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.053
ω scans	θ_max = 26.4°, θ_min = 2.8°
Absorption correction: numerical (CrysAlis PRO; Oxford Diffraction, 2010)	h = −13→11
T_min = 0.74, T_max = 0.91	k = −18→18
22593 measured reflections	l = −28→24

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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.110	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.042P)²] where P = (F_o² + 2F_c²)/3
7368 reflections	(Δ/σ)_max = 0.001
496 parameters	Δρ_max = 0.59 e Å⁻³
0 restraints	Δρ_min = −0.63 e Å⁻³

Crystal data top

[Cu(C₁₀H₈N₂)₃][Fe(CN)₅(NO)]·2CH₄O·H₂O	V = 3810.4 (5) Å³
M_r = 830.15	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 11.1308 (8) Å	µ = 1.00 mm⁻¹
b = 14.7928 (9) Å	T = 293 K
c = 23.1448 (17) Å	0.30 × 0.20 × 0.10 mm
β = 90.916 (8)°

Data collection top

Oxford Diffraction Xcalibur Sapphire3 diffractometer	7368 independent reflections
Absorption correction: numerical (CrysAlis PRO; Oxford Diffraction, 2010)	3799 reflections with I > 2σ(I)
T_min = 0.74, T_max = 0.91	R_int = 0.053
22593 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.051	0 restraints
wR(F²) = 0.110	H-atom parameters constrained
S = 1.01	Δρ_max = 0.59 e Å⁻³
7368 reflections	Δρ_min = −0.63 e Å⁻³
496 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
Fe1	0.54777 (5)	0.85655 (4)	0.08468 (3)	0.03893 (16)
Cu1	0.91414 (4)	0.80913 (3)	0.32784 (2)	0.04640 (16)
N1	1.0220 (3)	0.7802 (2)	0.26108 (16)	0.0497 (9)
N2	1.0506 (3)	0.8936 (2)	0.34517 (16)	0.0495 (9)
N3	0.7880 (3)	0.7182 (2)	0.30682 (14)	0.0382 (8)
N4	0.9782 (3)	0.7012 (2)	0.37086 (13)	0.0378 (8)
N5	0.8102 (3)	0.8510 (2)	0.39425 (14)	0.0416 (8)
N6	0.8275 (3)	0.9133 (2)	0.29055 (14)	0.0372 (8)
N7	0.2746 (3)	0.8839 (2)	0.06854 (17)	0.0620 (11)
N8	0.5926 (3)	1.0615 (2)	0.09581 (18)	0.0622 (11)
N9	0.8113 (4)	0.8198 (3)	0.11772 (19)	0.0731 (12)
N10	0.5011 (3)	0.6536 (3)	0.10134 (18)	0.0637 (11)
N11	0.4997 (3)	0.8746 (2)	0.21488 (17)	0.0534 (10)
N12	0.5814 (3)	0.8554 (2)	0.01612 (17)	0.0492 (9)
C1	1.0021 (4)	0.7186 (3)	0.2195 (2)	0.0605 (12)
H1A	0.9292	0.6879	0.2192	0.073*
C2	1.0812 (5)	0.6988 (3)	0.1786 (2)	0.0694 (14)
H2A	1.0634	0.6554	0.1507	0.083*
C3	1.1885 (5)	0.7432 (4)	0.1783 (2)	0.0765 (16)
H3A	1.2449	0.7309	0.1501	0.092*
C4	1.2113 (4)	0.8055 (4)	0.2197 (2)	0.0739 (15)
H4A	1.2843	0.8361	0.2203	0.089*
C5	1.1273 (4)	0.8241 (3)	0.2611 (2)	0.0502 (11)
C6	1.1399 (4)	0.8914 (3)	0.3066 (2)	0.0551 (12)
C7A	0.3757 (4)	0.8748 (3)	0.07377 (18)	0.0445 (10)
C7	1.2363 (5)	0.9509 (4)	0.3111 (3)	0.0795 (16)
H7A	1.3002	0.9470	0.2858	0.095*
C8A	0.5745 (3)	0.9855 (3)	0.09130 (19)	0.0474 (11)
C8	1.2348 (5)	1.0162 (4)	0.3542 (3)	0.0928 (19)
H8A	1.2970	1.0580	0.3572	0.111*
C9A	0.7126 (4)	0.8341 (3)	0.10677 (19)	0.0474 (11)
C9	1.1436 (5)	1.0192 (4)	0.3915 (3)	0.0841 (17)
H9A	1.1416	1.0631	0.4203	0.101*
C10A	0.5162 (3)	0.7285 (3)	0.09489 (19)	0.0456 (11)
C10	1.0541 (4)	0.9564 (3)	0.3865 (2)	0.0634 (13)
H10A	0.9925	0.9576	0.4131	0.076*
C11A	0.5175 (3)	0.8666 (3)	0.1664 (2)	0.0415 (10)
C11	0.6953 (4)	0.7304 (3)	0.2706 (2)	0.0497 (11)
H11A	0.6908	0.7842	0.2499	0.060*
C12	0.6073 (4)	0.6684 (3)	0.2625 (2)	0.0546 (12)
H12A	0.5442	0.6794	0.2367	0.066*
C13	0.6126 (4)	0.5887 (3)	0.2931 (2)	0.0586 (13)
H13A	0.5521	0.5457	0.2891	0.070*
C14	0.7075 (4)	0.5742 (3)	0.32919 (19)	0.0499 (11)
H14A	0.7130	0.5207	0.3501	0.060*
C15	0.7955 (3)	0.6383 (3)	0.33483 (17)	0.0409 (10)
C16	0.9060 (4)	0.6278 (3)	0.37029 (17)	0.0413 (10)
C17	0.9377 (4)	0.5503 (3)	0.39901 (19)	0.0548 (12)
H17A	0.8866	0.5005	0.3985	0.066*
C18	1.0445 (4)	0.5465 (3)	0.4283 (2)	0.0587 (13)
H18A	1.0673	0.4940	0.4477	0.070*
C19	1.1185 (4)	0.6208 (3)	0.42895 (19)	0.0575 (12)
H19A	1.1918	0.6197	0.4487	0.069*
C20	1.0814 (4)	0.6969 (3)	0.39965 (18)	0.0476 (11)
H20A	1.1311	0.7475	0.4001	0.057*
C21	0.8078 (4)	0.8163 (3)	0.44769 (18)	0.0479 (11)
H21A	0.8631	0.7716	0.4577	0.058*
C22	0.7276 (4)	0.8438 (3)	0.48790 (19)	0.0544 (12)
H22A	0.7277	0.8176	0.5244	0.065*
C23	0.6471 (4)	0.9102 (3)	0.4740 (2)	0.0600 (12)
H23A	0.5912	0.9294	0.5008	0.072*
C24	0.6497 (4)	0.9482 (3)	0.41990 (19)	0.0535 (12)
H24A	0.5957	0.9937	0.4097	0.064*
C25	0.7321 (3)	0.9188 (2)	0.38118 (18)	0.0399 (10)
C26	0.7462 (3)	0.9554 (2)	0.32274 (18)	0.0383 (9)
C27	0.6835 (3)	1.0305 (3)	0.30261 (19)	0.0479 (11)
H27A	0.6281	1.0595	0.3259	0.058*
C28	0.7047 (4)	1.0611 (3)	0.2478 (2)	0.0556 (12)
H28A	0.6630	1.1108	0.2333	0.067*
C29	0.7865 (4)	1.0186 (3)	0.21512 (19)	0.0535 (11)
H29A	0.8024	1.0394	0.1781	0.064*
C30	0.8463 (4)	0.9441 (3)	0.23692 (18)	0.0472 (11)
H30A	0.9012	0.9143	0.2138	0.057*
O1	0.6132 (3)	0.8586 (3)	−0.03055 (15)	0.0856 (11)
O1S	0.3532 (3)	0.7337 (3)	0.3573 (2)	0.1165 (16)
H1S	0.3516	0.6904	0.3794	0.175*
C1S	0.4416 (5)	0.7904 (4)	0.3736 (3)	0.105 (2)
H1SA	0.4424	0.8416	0.3482	0.158*
H1SB	0.5173	0.7595	0.3720	0.158*
H1SC	0.4282	0.8104	0.4125	0.158*
O2S	0.0815 (7)	0.8683 (4)	0.5202 (3)	0.178 (2)
H2S	0.0561	0.8220	0.5353	0.267*
C2S	0.2053 (8)	0.8635 (5)	0.5160 (4)	0.156 (4)
H2SA	0.2349	0.9175	0.4982	0.234*
H2SB	0.2262	0.8121	0.4930	0.234*
H2SC	0.2405	0.8573	0.5540	0.234*
O3S	1.0227 (3)	0.8062 (2)	0.04880 (15)	0.0899 (11)
H3SA	1.0827	0.8365	0.0613	0.135*
H3SB	0.9690	0.8129	0.0742	0.135*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Fe1	0.0380 (3)	0.0344 (3)	0.0444 (3)	0.0019 (3)	0.0002 (3)	0.0001 (3)
Cu1	0.0481 (3)	0.0407 (3)	0.0504 (3)	−0.0027 (2)	0.0019 (3)	0.0039 (3)
N1	0.045 (2)	0.045 (2)	0.059 (2)	0.0040 (17)	−0.006 (2)	0.008 (2)
N2	0.049 (2)	0.046 (2)	0.054 (2)	−0.0050 (18)	−0.011 (2)	0.014 (2)
N3	0.0303 (18)	0.0397 (18)	0.045 (2)	0.0001 (15)	−0.0026 (17)	0.0103 (17)
N4	0.0359 (19)	0.0405 (18)	0.0371 (18)	0.0027 (15)	−0.0009 (17)	0.0014 (17)
N5	0.044 (2)	0.0390 (18)	0.041 (2)	−0.0027 (16)	−0.0012 (17)	0.0017 (18)
N6	0.0386 (19)	0.0361 (17)	0.0368 (19)	−0.0056 (15)	−0.0055 (17)	0.0013 (17)
N7	0.047 (2)	0.065 (2)	0.073 (3)	0.006 (2)	−0.008 (2)	−0.007 (2)
N8	0.064 (2)	0.041 (2)	0.081 (3)	−0.0053 (19)	−0.002 (2)	0.005 (2)
N9	0.048 (2)	0.091 (3)	0.081 (3)	0.015 (2)	−0.003 (2)	−0.016 (3)
N10	0.070 (3)	0.041 (2)	0.080 (3)	−0.004 (2)	0.009 (2)	−0.004 (2)
N11	0.061 (2)	0.051 (2)	0.049 (2)	0.0053 (18)	0.004 (2)	0.005 (2)
N12	0.055 (2)	0.0411 (19)	0.051 (2)	0.0139 (18)	−0.0027 (19)	0.004 (2)
C1	0.062 (3)	0.060 (3)	0.060 (3)	0.009 (3)	0.000 (3)	0.002 (3)
C2	0.086 (4)	0.063 (3)	0.060 (3)	0.010 (3)	0.002 (3)	0.000 (3)
C3	0.089 (4)	0.077 (4)	0.065 (4)	0.017 (3)	0.023 (3)	0.013 (3)
C4	0.053 (3)	0.084 (4)	0.085 (4)	−0.006 (3)	0.009 (3)	0.028 (4)
C5	0.035 (2)	0.059 (3)	0.057 (3)	0.001 (2)	−0.001 (2)	0.021 (3)
C6	0.044 (3)	0.052 (3)	0.069 (3)	−0.011 (2)	−0.010 (3)	0.019 (3)
C7A	0.051 (3)	0.040 (2)	0.042 (2)	0.000 (2)	0.000 (2)	−0.003 (2)
C7	0.062 (3)	0.087 (4)	0.089 (4)	−0.029 (3)	−0.011 (3)	0.020 (4)
C8A	0.042 (2)	0.046 (3)	0.054 (3)	0.000 (2)	−0.001 (2)	0.009 (2)
C8	0.084 (4)	0.078 (4)	0.116 (5)	−0.043 (4)	−0.024 (4)	0.016 (4)
C9A	0.051 (3)	0.042 (2)	0.049 (3)	0.000 (2)	0.009 (2)	−0.006 (2)
C9	0.092 (4)	0.068 (3)	0.092 (4)	−0.022 (3)	−0.020 (4)	−0.003 (3)
C10A	0.039 (2)	0.045 (2)	0.053 (3)	0.006 (2)	0.001 (2)	−0.007 (2)
C10	0.065 (3)	0.054 (3)	0.071 (3)	−0.014 (3)	−0.009 (3)	0.001 (3)
C11A	0.031 (2)	0.030 (2)	0.063 (3)	0.0012 (17)	−0.001 (2)	0.004 (2)
C11	0.043 (3)	0.041 (2)	0.065 (3)	−0.004 (2)	0.002 (3)	0.009 (2)
C12	0.039 (2)	0.054 (3)	0.070 (3)	−0.006 (2)	−0.012 (2)	0.005 (3)
C13	0.051 (3)	0.044 (3)	0.080 (4)	−0.014 (2)	−0.006 (3)	−0.005 (3)
C14	0.051 (3)	0.038 (2)	0.060 (3)	−0.004 (2)	0.001 (3)	0.008 (2)
C15	0.041 (2)	0.037 (2)	0.046 (2)	−0.002 (2)	0.008 (2)	0.002 (2)
C16	0.043 (2)	0.040 (2)	0.041 (2)	0.0016 (19)	0.006 (2)	0.005 (2)
C17	0.058 (3)	0.041 (2)	0.065 (3)	−0.002 (2)	−0.001 (3)	0.012 (2)
C18	0.066 (3)	0.054 (3)	0.057 (3)	0.019 (3)	0.001 (3)	0.014 (3)
C19	0.045 (3)	0.080 (3)	0.047 (3)	0.018 (3)	−0.001 (2)	0.000 (3)
C20	0.042 (3)	0.050 (3)	0.050 (3)	0.002 (2)	−0.006 (2)	0.001 (2)
C21	0.055 (3)	0.043 (2)	0.045 (3)	−0.005 (2)	−0.003 (2)	0.006 (2)
C22	0.075 (3)	0.045 (3)	0.043 (3)	−0.015 (2)	−0.002 (3)	0.003 (2)
C23	0.077 (3)	0.052 (3)	0.052 (3)	−0.002 (3)	0.021 (3)	−0.006 (3)
C24	0.059 (3)	0.043 (2)	0.059 (3)	0.004 (2)	0.009 (3)	0.004 (2)
C25	0.044 (2)	0.033 (2)	0.044 (2)	−0.0062 (19)	0.003 (2)	−0.002 (2)
C26	0.033 (2)	0.035 (2)	0.046 (2)	−0.0043 (18)	−0.008 (2)	−0.002 (2)
C27	0.044 (2)	0.043 (2)	0.057 (3)	0.007 (2)	0.003 (2)	0.002 (2)
C28	0.054 (3)	0.046 (3)	0.066 (3)	0.005 (2)	−0.010 (3)	0.013 (3)
C29	0.060 (3)	0.053 (3)	0.047 (3)	−0.004 (2)	−0.005 (2)	0.017 (2)
C30	0.047 (3)	0.050 (3)	0.044 (3)	−0.005 (2)	0.003 (2)	0.002 (2)
O1	0.110 (3)	0.098 (3)	0.050 (2)	0.035 (2)	0.013 (2)	0.014 (2)
O1S	0.088 (3)	0.082 (3)	0.179 (5)	−0.010 (2)	−0.029 (3)	0.043 (3)
C1S	0.088 (4)	0.071 (4)	0.156 (6)	−0.005 (3)	−0.022 (4)	0.000 (4)
O2S	0.218 (6)	0.121 (4)	0.195 (6)	0.030 (5)	0.014 (6)	0.055 (4)
C2S	0.176 (8)	0.128 (6)	0.161 (8)	−0.077 (7)	−0.073 (7)	0.047 (6)
O3S	0.079 (2)	0.111 (3)	0.081 (3)	−0.002 (2)	0.013 (2)	−0.002 (2)

Geometric parameters (Å, º) top

Fe1—N12	1.636 (4)	C11—C12	1.353 (5)
Fe1—C9A	1.926 (5)	C11—H11A	0.9300
Fe1—C11A	1.932 (5)	C12—C13	1.376 (6)
Fe1—C8A	1.936 (4)	C12—H12A	0.9300
Fe1—C10A	1.942 (5)	C13—C14	1.353 (6)
Fe1—C7A	1.947 (5)	C13—H13A	0.9300
Cu1—N3	1.999 (3)	C14—C15	1.368 (5)
Cu1—N2	2.002 (3)	C14—H14A	0.9300
Cu1—N6	2.006 (3)	C15—C16	1.476 (5)
Cu1—N4	2.006 (3)	C16—C17	1.370 (5)
Cu1—N1	2.018 (4)	C17—C18	1.360 (6)
Cu1—N5	2.035 (3)	C17—H17A	0.9300
N1—C5	1.340 (5)	C18—C19	1.374 (6)
N1—C1	1.341 (5)	C18—H18A	0.9300
N2—C10	1.333 (5)	C19—C20	1.374 (6)
N2—C6	1.347 (5)	C19—H19A	0.9300
N3—C11	1.331 (5)	C20—H20A	0.9300
N3—C15	1.349 (5)	C21—C22	1.362 (6)
N4—C20	1.321 (5)	C21—H21A	0.9300
N4—C16	1.350 (5)	C22—C23	1.364 (6)
N5—C21	1.340 (5)	C22—H22A	0.9300
N5—C25	1.359 (5)	C23—C24	1.374 (6)
N6—C26	1.336 (5)	C23—H23A	0.9300
N6—C30	1.342 (5)	C24—C25	1.364 (5)
N7—C7A	1.138 (5)	C24—H24A	0.9300
N8—C8A	1.147 (5)	C25—C26	1.467 (5)
N9—C9A	1.144 (5)	C26—C27	1.389 (5)
N10—C10A	1.130 (5)	C27—C28	1.371 (6)
N11—C11A	1.149 (5)	C27—H27A	0.9300
N12—O1	1.143 (4)	C28—C29	1.349 (6)
C1—C2	1.337 (6)	C28—H28A	0.9300
C1—H1A	0.9300	C29—C30	1.379 (5)
C2—C3	1.363 (7)	C29—H29A	0.9300
C2—H2A	0.9300	C30—H30A	0.9300
C3—C4	1.351 (7)	O1S—C1S	1.342 (6)
C3—H3A	0.9300	O1S—H1S	0.8200
C4—C5	1.377 (6)	C1S—H1SA	0.9600
C4—H4A	0.9300	C1S—H1SB	0.9600
C5—C6	1.455 (6)	C1S—H1SC	0.9602
C6—C7	1.390 (6)	O2S—C2S	1.384 (8)
C7—C8	1.389 (8)	O2S—H2S	0.8201
C7—H7A	0.9300	C2S—H2SA	0.9599
C8—C9	1.345 (8)	C2S—H2SB	0.9601
C8—H8A	0.9300	C2S—H2SC	0.9601
C9—C10	1.365 (6)	O3S—H3SA	0.8500
C9—H9A	0.9300	O3S—H3SB	0.8499
C10—H10A	0.9300

N12—Fe1—C9A	91.36 (17)	N2—C10—C9	123.3 (5)
N12—Fe1—C11A	175.03 (17)	N2—C10—H10A	118.4
C9A—Fe1—C11A	86.19 (17)	C9—C10—H10A	118.4
N12—Fe1—C8A	92.83 (18)	N11—C11A—Fe1	178.5 (4)
C9A—Fe1—C8A	90.23 (16)	N3—C11—C12	123.1 (4)
C11A—Fe1—C8A	82.87 (17)	N3—C11—H11A	118.4
N12—Fe1—C10A	98.79 (18)	C12—C11—H11A	118.4
C9A—Fe1—C10A	88.45 (16)	C11—C12—C13	119.0 (4)
C11A—Fe1—C10A	85.48 (17)	C11—C12—H12A	120.5
C8A—Fe1—C10A	168.33 (19)	C13—C12—H12A	120.5
N12—Fe1—C7A	96.65 (17)	C14—C13—C12	118.6 (4)
C9A—Fe1—C7A	171.75 (17)	C14—C13—H13A	120.7
C11A—Fe1—C7A	85.97 (16)	C12—C13—H13A	120.7
C8A—Fe1—C7A	91.33 (16)	C13—C14—C15	120.0 (4)
C10A—Fe1—C7A	88.39 (16)	C13—C14—H14A	120.0
N3—Cu1—N2	175.02 (14)	C15—C14—H14A	120.0
N3—Cu1—N6	94.69 (12)	N3—C15—C14	121.5 (4)
N2—Cu1—N6	87.97 (12)	N3—C15—C16	113.8 (3)
N3—Cu1—N4	80.07 (13)	C14—C15—C16	124.7 (4)
N2—Cu1—N4	97.75 (13)	N4—C16—C17	121.4 (4)
N6—Cu1—N4	171.67 (13)	N4—C16—C15	114.3 (3)
N3—Cu1—N1	95.46 (13)	C17—C16—C15	124.3 (4)
N2—Cu1—N1	80.02 (15)	C18—C17—C16	119.5 (4)
N6—Cu1—N1	96.94 (13)	C18—C17—H17A	120.2
N4—Cu1—N1	90.04 (12)	C16—C17—H17A	120.2
N3—Cu1—N5	89.03 (13)	C17—C18—C19	119.4 (4)
N2—Cu1—N5	95.60 (14)	C17—C18—H18A	120.3
N6—Cu1—N5	79.41 (13)	C19—C18—H18A	120.3
N4—Cu1—N5	93.94 (13)	C18—C19—C20	118.4 (4)
N1—Cu1—N5	174.46 (13)	C18—C19—H19A	120.8
C5—N1—C1	117.7 (4)	C20—C19—H19A	120.8
C5—N1—Cu1	115.4 (3)	N4—C20—C19	122.7 (4)
C1—N1—Cu1	126.8 (3)	N4—C20—H20A	118.6
C10—N2—C6	118.6 (4)	C19—C20—H20A	118.6
C10—N2—Cu1	126.3 (3)	N5—C21—C22	122.6 (4)
C6—N2—Cu1	114.7 (3)	N5—C21—H21A	118.7
C11—N3—C15	117.6 (3)	C22—C21—H21A	118.7
C11—N3—Cu1	126.6 (3)	C21—C22—C23	119.3 (4)
C15—N3—Cu1	115.8 (3)	C21—C22—H22A	120.4
C20—N4—C16	118.6 (3)	C23—C22—H22A	120.4
C20—N4—Cu1	126.0 (3)	C22—C23—C24	119.1 (4)
C16—N4—Cu1	115.4 (3)	C22—C23—H23A	120.5
C21—N5—C25	117.8 (3)	C24—C23—H23A	120.5
C21—N5—Cu1	126.9 (3)	C25—C24—C23	119.5 (4)
C25—N5—Cu1	115.2 (3)	C25—C24—H24A	120.2
C26—N6—C30	118.3 (3)	C23—C24—H24A	120.2
C26—N6—Cu1	116.3 (3)	N5—C25—C24	121.6 (4)
C30—N6—Cu1	125.3 (3)	N5—C25—C26	113.6 (3)
O1—N12—Fe1	174.4 (4)	C24—C25—C26	124.8 (4)
C2—C1—N1	123.6 (5)	N6—C26—C27	121.8 (4)
C2—C1—H1A	118.2	N6—C26—C25	115.2 (3)
N1—C1—H1A	118.2	C27—C26—C25	123.0 (4)
C1—C2—C3	119.1 (5)	C28—C27—C26	118.8 (4)
C1—C2—H2A	120.5	C28—C27—H27A	120.6
C3—C2—H2A	120.5	C26—C27—H27A	120.6
C4—C3—C2	118.7 (5)	C29—C28—C27	119.5 (4)
C4—C3—H3A	120.7	C29—C28—H28A	120.2
C2—C3—H3A	120.7	C27—C28—H28A	120.2
C3—C4—C5	120.5 (5)	C28—C29—C30	119.6 (4)
C3—C4—H4A	119.7	C28—C29—H29A	120.2
C5—C4—H4A	119.7	C30—C29—H29A	120.2
N1—C5—C4	120.5 (5)	N6—C30—C29	121.9 (4)
N1—C5—C6	113.9 (4)	N6—C30—H30A	119.0
C4—C5—C6	125.6 (5)	C29—C30—H30A	119.0
N2—C6—C7	120.9 (5)	C1S—O1S—H1S	109.6
N2—C6—C5	115.6 (4)	O1S—C1S—H1SA	109.6
C7—C6—C5	123.5 (5)	O1S—C1S—H1SB	109.4
N7—C7A—Fe1	178.1 (4)	H1SA—C1S—H1SB	109.5
C8—C7—C6	118.4 (5)	O1S—C1S—H1SC	109.4
C8—C7—H7A	120.8	H1SA—C1S—H1SC	109.5
C6—C7—H7A	120.8	H1SB—C1S—H1SC	109.5
N8—C8A—Fe1	178.6 (4)	C2S—O2S—H2S	109.7
C9—C8—C7	120.2 (5)	O2S—C2S—H2SA	109.7
C9—C8—H8A	119.9	O2S—C2S—H2SB	109.3
C7—C8—H8A	119.9	H2SA—C2S—H2SB	109.5
N9—C9A—Fe1	177.3 (4)	O2S—C2S—H2SC	109.4
C8—C9—C10	118.7 (6)	H2SA—C2S—H2SC	109.5
C8—C9—H9A	120.7	H2SB—C2S—H2SC	109.5
C10—C9—H9A	120.7	H3SA—O3S—H3SB	105.2
N10—C10A—Fe1	178.0 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3S—H3SB···N9	0.85	2.04	2.870 (5)	165
O3S—H3SA···N7ⁱ	0.85	2.25	3.058 (5)	158
O1S—H1S···N8ⁱⁱ	0.82	2.08	2.831 (5)	151
O2S—H2S···O3Sⁱⁱⁱ	0.82	1.96	2.746 (7)	161

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

Experimental details

Crystal data
Chemical formula	[Cu(C₁₀H₈N₂)₃][Fe(CN)₅(NO)]·2CH₄O·H₂O
M_r	830.15
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	11.1308 (8), 14.7928 (9), 23.1448 (17)
β (°)	90.916 (8)
V (Å³)	3810.4 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.00
Crystal size (mm)	0.30 × 0.20 × 0.10

Data collection
Diffractometer	Oxford Diffraction Xcalibur Sapphire3 diffractometer
Absorption correction	Numerical (CrysAlis PRO; Oxford Diffraction, 2010)
T_min, T_max	0.74, 0.91
No. of measured, independent and observed [I > 2σ(I)] reflections	22593, 7368, 3799
R_int	0.053
(sin θ/λ)_max (Å⁻¹)	0.625

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.051, 0.110, 1.01
No. of reflections	7368
No. of parameters	496
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.59, −0.63

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3S—H3SB···N9	0.85	2.04	2.870 (5)	165.2
O3S—H3SA···N7ⁱ	0.85	2.25	3.058 (5)	158.1
O1S—H1S···N8ⁱⁱ	0.82	2.08	2.831 (5)	151.4
O2S—H2S···O3Sⁱⁱⁱ	0.82	1.96	2.746 (7)	160.6

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

References

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Volume 69| Part 4| April 2013| Pages m212-m213

doi:10.1107/S1600536813006867

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

Tris(2,2′-bi­pyridine)­copper(II) penta­cyanido­nitro­soferrate(II) methanol disolvate monohydrate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

References

metal-organic compounds

Tris(2,2′-bipyridine)copper(II) pentacyanidonitrosoferrate(II) methanol disolvate monohydrate