Bis{2-[N,N-bis(2-amino­ethyl)amino]­ethan­aminium}­nickel(II) hexa­cyanidoferrate(II)

In the title compound, [Ni(C₆H₁₉N₄)₂][Fe(CN)₆], the Ni²⁺ and Fe²⁺ cations are both octa­hedrally coordinated. The complex cations and anions, both of which are centrosymmetric, are linked by a network of N—H...N hydrogen bonds to form a three-dimensional network.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.032
• wR factor = 0.083
• Data-to-parameter ratio = 16.6

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT030_ALERT_1_C _diffrn_reflns_number .LE.  _reflns_number_total          ?
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.99
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent .....          ?
PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000)        3000 Deg.
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Fe1    -   C7      ..       9.60 su
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Fe1    -   C8      ..       9.03 su
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Fe1    -   C9      ..       9.84 su

Alert level G
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   7 ALERT level C = Check and explain
   2 ALERT level G = General alerts; check

   5 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software; data reduction: MolEN (Fair, 1990); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP (Siemens, 1994); software used to prepare material for publication: SHELXTL (Siemens, 1995).

{N-[N,N-Bis(2-aminoethyl)amino]ethanaminium]}nickel(II)] hexacyanidoferrate(II)

Crystal data

[Ni(C6H19N4)2][Fe(CN)6]	Z = 1
Mr = 565.18	F(000) = 298
Triclinic, P1	Dx = 1.547 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.6744 (17) Å	Cell parameters from 25 reflections
b = 8.7883 (18) Å	θ = 14.9–16.0°
c = 9.3802 (19) Å	µ = 1.41 mm^−1
α = 92.45 (3)°	T = 293 K
β = 99.70 (3)°	Block, red
γ = 119.56 (3)°	0.48 × 0.35 × 0.20 mm
V = 606.5 (2) Å^3

Data collection

Enraf–Nonius CAD-4 diffractometer	2350 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.000
Graphite monochromator	θmax = 27.0°, θmin = 2.2°
ω/2θ scans	h = −11→0
Absorption correction: ψ scan (North et al., 1968)	k = −9→11
Tmin = 0.551, Tmax = 0.765	l = −11→11
2632 measured reflections	3 standard reflections every 97 reflections
2632 independent reflections	intensity decay: none

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.032	H-atom parameters constrained
wR(F^2) = 0.083	w = 1/[σ^2(Fo^2) + (0.0525P)^2 + 0.3859P] where P = (Fo^2 + 2Fc^2)/3
S = 0.97	(Δ/σ)max < 0.001
2632 reflections	Δρmax = 0.39 e Å^−3
159 parameters	Δρmin = −0.67 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.072 (4)

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
Ni1	0.5000	0.5000	0.5000	0.02007 (13)
Fe1	0.5000	1.0000	1.0000	0.02107 (13)
N1	0.3089 (2)	0.4080 (2)	0.63209 (18)	0.0276 (4)
H1A	0.3196	0.3272	0.6820	0.033*
H1B	0.3319	0.4986	0.6974	0.033*
N2	0.5202 (3)	0.7528 (2)	0.51491 (19)	0.0296 (4)
H2A	0.5679	0.8085	0.6076	0.036*
H2B	0.5923	0.8203	0.4573	0.036*
N3	0.2635 (2)	0.4335 (2)	0.33354 (17)	0.0229 (3)
N4	0.1203 (2)	0.2641 (2)	−0.07164 (19)	0.0303 (4)
H4A	0.1735	0.3700	−0.1003	0.045*
H4B	0.0131	0.1942	−0.1321	0.045*
H4C	0.1902	0.2168	−0.0728	0.045*
N5	0.2451 (3)	0.9657 (2)	1.2025 (2)	0.0339 (4)
N6	0.2564 (3)	0.6101 (2)	0.8684 (2)	0.0418 (5)
N7	0.2923 (3)	1.1052 (3)	0.7672 (2)	0.0421 (5)
C1	0.1217 (3)	0.3276 (3)	0.5449 (2)	0.0360 (5)
H1C	0.0774	0.4085	0.5559	0.043*
H1D	0.0435	0.2199	0.5808	0.043*
C2	0.1142 (3)	0.2855 (3)	0.3850 (2)	0.0320 (5)
H2C	0.1224	0.1800	0.3702	0.038*
H2D	−0.0015	0.2612	0.3273	0.038*
C3	0.3361 (3)	0.7226 (3)	0.4671 (2)	0.0321 (5)
H3A	0.3419	0.8332	0.4502	0.038*
H3B	0.2679	0.6764	0.5423	0.038*
C4	0.2426 (3)	0.5914 (3)	0.3271 (2)	0.0294 (4)
H4D	0.1143	0.5528	0.3067	0.035*
H4E	0.2921	0.6505	0.2470	0.035*
C5	0.2739 (3)	0.3727 (3)	0.1878 (2)	0.0255 (4)
H5A	0.3185	0.2911	0.1984	0.031*
H5B	0.3610	0.4737	0.1498	0.031*
C6	0.0936 (3)	0.2826 (3)	0.0782 (2)	0.0310 (5)
H6A	0.0152	0.1666	0.1025	0.037*
H6B	0.0347	0.3515	0.0832	0.037*
C7	0.3399 (3)	0.9770 (2)	1.1258 (2)	0.0252 (4)
C8	0.3471 (3)	0.7572 (3)	0.9176 (2)	0.0270 (4)
C9	0.3702 (3)	1.0645 (3)	0.8541 (2)	0.0276 (4)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Ni1	0.0239 (2)	0.02026 (19)	0.01702 (19)	0.01223 (15)	0.00363 (13)	0.00265 (12)
Fe1	0.0244 (2)	0.0159 (2)	0.0215 (2)	0.00954 (16)	0.00411 (15)	0.00185 (14)
N1	0.0330 (9)	0.0306 (9)	0.0219 (8)	0.0173 (8)	0.0081 (7)	0.0059 (7)
N2	0.0373 (10)	0.0252 (8)	0.0249 (8)	0.0173 (8)	0.0001 (7)	−0.0010 (7)
N3	0.0257 (8)	0.0227 (8)	0.0191 (7)	0.0121 (7)	0.0031 (6)	0.0020 (6)
N4	0.0316 (9)	0.0269 (9)	0.0247 (9)	0.0095 (7)	0.0059 (7)	−0.0006 (7)
N5	0.0343 (10)	0.0312 (9)	0.0314 (9)	0.0132 (8)	0.0084 (8)	−0.0018 (7)
N6	0.0479 (12)	0.0233 (9)	0.0455 (12)	0.0112 (9)	0.0136 (10)	−0.0020 (8)
N7	0.0394 (11)	0.0434 (11)	0.0478 (12)	0.0236 (10)	0.0088 (9)	0.0186 (9)
C1	0.0305 (11)	0.0435 (13)	0.0311 (11)	0.0148 (10)	0.0120 (9)	0.0089 (9)
C2	0.0270 (10)	0.0329 (11)	0.0290 (11)	0.0099 (9)	0.0060 (8)	0.0050 (8)
C3	0.0405 (12)	0.0316 (11)	0.0310 (11)	0.0248 (10)	0.0038 (9)	0.0011 (8)
C4	0.0330 (11)	0.0319 (10)	0.0271 (10)	0.0214 (9)	0.0004 (8)	0.0027 (8)
C5	0.0272 (10)	0.0273 (10)	0.0223 (9)	0.0143 (8)	0.0048 (8)	0.0021 (7)
C6	0.0274 (10)	0.0368 (11)	0.0204 (10)	0.0107 (9)	0.0039 (8)	0.0006 (8)
C7	0.0269 (9)	0.0178 (9)	0.0260 (10)	0.0097 (7)	0.0001 (8)	−0.0001 (7)
C8	0.0310 (10)	0.0250 (10)	0.0252 (10)	0.0137 (8)	0.0081 (8)	0.0038 (8)
C9	0.0285 (10)	0.0222 (9)	0.0321 (10)	0.0116 (8)	0.0102 (8)	0.0057 (8)

Geometric parameters (Å, º)

Ni1—N1^i	2.0956 (19)	N4—H4A	0.8900
Ni1—N1	2.0956 (19)	N4—H4B	0.8900
Ni1—N2^i	2.1369 (17)	N4—H4C	0.8900
Ni1—N2	2.1369 (17)	N5—C7	1.153 (3)
Ni1—N3	2.1558 (18)	N6—C8	1.151 (3)
Ni1—N3^i	2.1558 (18)	N7—C9	1.152 (3)
Fe1—C9	1.907 (2)	C1—C2	1.513 (3)
Fe1—C9^ii	1.907 (2)	C1—H1C	0.9700
Fe1—C7^ii	1.912 (2)	C1—H1D	0.9700
Fe1—C7	1.912 (2)	C2—H2C	0.9700
Fe1—C8	1.906 (2)	C2—H2D	0.9700
Fe1—C8^ii	1.906 (2)	C3—C4	1.516 (3)
N1—C1	1.475 (3)	C3—H3A	0.9700
N1—H1A	0.9000	C3—H3B	0.9700
N1—H1B	0.9000	C4—H4D	0.9700
N2—C3	1.467 (3)	C4—H4E	0.9700
N2—H2A	0.9000	C5—C6	1.516 (3)
N2—H2B	0.9000	C5—H5A	0.9700
N3—C5	1.480 (2)	C5—H5B	0.9700
N3—C4	1.488 (3)	C6—H6A	0.9700
N3—C2	1.484 (3)	C6—H6B	0.9700
N4—C6	1.478 (3)
N1^i—Ni1—N1	180.0	C2—N3—Ni1	103.13 (12)
N1^i—Ni1—N2^i	91.77 (8)	C6—N4—H4A	109.5
N1—Ni1—N2^i	88.23 (8)	C6—N4—H4B	109.5
N1^i—Ni1—N2	88.23 (8)	H4A—N4—H4B	109.5
N1—Ni1—N2	91.77 (8)	C6—N4—H4C	109.5
N1^i—Ni1—N3	97.77 (7)	H4A—N4—H4C	109.5
N1—Ni1—N3	82.23 (7)	H4B—N4—H4C	109.5
N1^i—Ni1—N3^i	82.23 (7)	N1—C1—C2	110.95 (18)
N1—Ni1—N3^i	97.77 (7)	N1—C1—H1C	109.4
N2^i—Ni1—N2	180.0	C2—C1—H1C	109.4
N2^i—Ni1—N3	98.33 (7)	N1—C1—H1D	109.4
N2—Ni1—N3	81.67 (7)	C2—C1—H1D	109.4
N2^i—Ni1—N3^i	81.67 (7)	H1C—C1—H1D	108.0
N2—Ni1—N3^i	98.33 (7)	N3—C2—C1	111.80 (18)
N3—Ni1—N3^i	180.0	N3—C2—H2C	109.3
C9—Fe1—C9^ii	180.0	C1—C2—H2C	109.3
C9—Fe1—C7^ii	89.59 (9)	N3—C2—H2D	109.3
C9^ii—Fe1—C7^ii	90.41 (9)	C1—C2—H2D	109.3
C9—Fe1—C7	90.41 (9)	H2C—C2—H2D	107.9
C9^ii—Fe1—C7	89.59 (9)	N2—C3—C4	109.03 (17)
C7^ii—Fe1—C7	180.0	N2—C3—H3A	109.9
C9—Fe1—C8	90.51 (9)	C4—C3—H3A	109.9
C9^ii—Fe1—C8	89.49 (9)	N2—C3—H3B	109.9
C7^ii—Fe1—C8	89.22 (9)	C4—C3—H3B	109.9
C7—Fe1—C8	90.78 (9)	H3A—C3—H3B	108.3
C9—Fe1—C8^ii	89.49 (9)	N3—C4—C3	113.36 (16)
C9^ii—Fe1—C8^ii	90.51 (9)	N3—C4—H4D	108.9
C7^ii—Fe1—C8^ii	90.77 (9)	C3—C4—H4D	108.9
C7—Fe1—C8^ii	89.22 (9)	N3—C4—H4E	108.9
C8—Fe1—C8^ii	180.0	C3—C4—H4E	108.9
C1—N1—Ni1	111.72 (13)	H4D—C4—H4E	107.7
C1—N1—H1A	109.3	N3—C5—C6	113.54 (17)
Ni1—N1—H1A	109.3	N3—C5—H5A	108.9
C1—N1—H1B	109.3	C6—C5—H5A	108.9
Ni1—N1—H1B	109.3	N3—C5—H5B	108.9
H1A—N1—H1B	107.9	C6—C5—H5B	108.9
C3—N2—Ni1	107.36 (13)	H5A—C5—H5B	107.7
C3—N2—H2A	110.2	N4—C6—C5	110.70 (17)
Ni1—N2—H2A	110.2	N4—C6—H6A	109.5
C3—N2—H2B	110.2	C5—C6—H6A	109.5
Ni1—N2—H2B	110.2	N4—C6—H6B	109.5
H2A—N2—H2B	108.5	C5—C6—H6B	109.5
C5—N3—C4	109.79 (15)	H6A—C6—H6B	108.1
C5—N3—C2	109.59 (16)	N5—C7—Fe1	179.01 (19)
C4—N3—C2	112.87 (17)	N6—C8—Fe1	179.2 (2)
C5—N3—Ni1	112.66 (12)	N7—C9—Fe1	179.1 (2)
C4—N3—Ni1	108.71 (12)
N2^i—Ni1—N1—C1	−91.04 (16)	N1—Ni1—N3—C2	−29.54 (13)
N2—Ni1—N1—C1	88.96 (16)	N2^i—Ni1—N3—C2	57.51 (13)
N3—Ni1—N1—C1	7.62 (15)	N2—Ni1—N3—C2	−122.49 (13)
N3^i—Ni1—N1—C1	−172.38 (15)	Ni1—N1—C1—C2	16.5 (2)
N1^i—Ni1—N2—C3	125.09 (14)	C5—N3—C2—C1	168.07 (18)
N1—Ni1—N2—C3	−54.91 (14)	C4—N3—C2—C1	−69.2 (2)
N3—Ni1—N2—C3	26.96 (13)	Ni1—N3—C2—C1	47.9 (2)
N3^i—Ni1—N2—C3	−153.04 (13)	N1—C1—C2—N3	−44.8 (3)
N1^i—Ni1—N3—C5	32.40 (13)	Ni1—N2—C3—C4	−46.2 (2)
N1—Ni1—N3—C5	−147.60 (13)	C5—N3—C4—C3	−146.12 (18)
N2^i—Ni1—N3—C5	−60.55 (14)	C2—N3—C4—C3	91.3 (2)
N2—Ni1—N3—C5	119.45 (14)	Ni1—N3—C4—C3	−22.5 (2)
N1^i—Ni1—N3—C4	−89.52 (14)	N2—C3—C4—N3	46.8 (2)
N1—Ni1—N3—C4	90.48 (14)	C4—N3—C5—C6	−73.2 (2)
N2^i—Ni1—N3—C4	177.53 (13)	C2—N3—C5—C6	51.3 (2)
N2—Ni1—N3—C4	−2.47 (13)	Ni1—N3—C5—C6	165.49 (14)
N1^i—Ni1—N3—C2	150.46 (13)	N3—C5—C6—N4	166.40 (16)

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···N7^iii	0.90	2.06	2.946 (3)	168
N1—H1B···N6	0.90	2.20	3.014 (3)	151
N2—H2A···N5^ii	0.90	2.30	3.153 (3)	158
N2—H2B···N7^iv	0.90	2.46	3.307 (3)	157
N4—H4A···N6^v	0.89	1.92	2.791 (3)	166
N4—H4B···N5^vi	0.89	1.94	2.792 (3)	161
N4—H4C···N7^vii	0.89	2.27	3.016 (3)	141

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