Bis[2-(amino­methyl)­pyridine-κ²N,N′]­dinitrato­iron(II)

The title compound, [Fe(NO₃)₂(C₆H₈N₂)₂], is a mononuclear centrosymmetric iron(II) complex. The Fe^II ion is coordinated by four N atoms from two 2-amino­methyl­pyridine ligands and two O atoms from two nitrate anions. The six atoms around the metal constitute a slightly distorted octahedral geometry. In the crystal structure, the mol­ecules are held together by intermolecular N—H...O hydrogen bonds, forming a three-dimensional network.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.010 Å
• R factor = 0.077
• wR factor = 0.179
• Data-to-parameter ratio = 13.9

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Fe1    -   N1      ..       8.63 su
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Fe1    -   N2      ..       9.88 su
PLAT241_ALERT_2_C Check High   U(eq) as Compared to Neighbors  for         O1
PLAT242_ALERT_2_C Check Low    U(eq) as Compared to Neighbors  for        Fe1
PLAT242_ALERT_2_C Check Low    U(eq) as Compared to Neighbors  for         N3
PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...         10
PLAT480_ALERT_4_C Long H...A H-Bond Reported H2B    ..  O2      ..       2.65 Ang.

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

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

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Computing details

Data collection: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Bis(2-aminomethylpyridine-κ²N,N')dinitratoiron(II)

Crystal data

[Fe(NO3)2(C6H8N2)2]	F(000) = 408
Mr = 396.16	Dx = 1.699 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 462 reflections
a = 8.781 (2) Å	θ = 2.4–20.7°
b = 8.845 (2) Å	µ = 1.02 mm^−1
c = 10.171 (2) Å	T = 293 K
β = 101.34 (3)°	Block, brown
V = 774.5 (3) Å^3	0.22 × 0.18 × 0.12 mm
Z = 2

Data collection

Bruker SMART CCD area-detector diffractometer	1596 independent reflections
Radiation source: fine-focus sealed tube	900 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.098
ω scans	θmax = 26.5°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→5
Tmin = 0.807, Tmax = 0.887	k = −11→11
3482 measured reflections	l = −12→12

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.077	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.179	H-atom parameters constrained
S = 0.95	w = 1/[σ^2(Fo^2) + (0.0752P)^2] where P = (Fo^2 + 2Fc^2)/3
1596 reflections	(Δ/σ)max < 0.001
115 parameters	Δρmax = 0.87 e Å^−3
0 restraints	Δρmin = −0.59 e Å^−3

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
Fe1	1.0000	0.0000	1.0000	0.0273 (4)
O1	1.0647 (6)	0.2371 (5)	0.9370 (4)	0.0584 (15)
O2	1.2000 (7)	0.4427 (6)	0.9643 (5)	0.0830 (19)
O3	1.1535 (6)	0.3236 (5)	1.1364 (4)	0.0612 (15)
N1	0.7619 (6)	0.0548 (6)	0.9299 (5)	0.0417 (14)
N2	0.9403 (6)	0.0738 (6)	1.1769 (5)	0.0450 (14)
H2A	0.9139	−0.0058	1.2228	0.054*
H2B	1.0221	0.1201	1.2283	0.054*
N3	1.1413 (7)	0.3346 (6)	1.0144 (5)	0.0438 (14)
C1	0.7029 (8)	0.1426 (7)	1.0150 (6)	0.0413 (16)
C2	0.5534 (8)	0.1961 (8)	0.9837 (7)	0.0512 (19)
H2	0.5167	0.2591	1.0438	0.061*
C3	0.4583 (8)	0.1584 (7)	0.8661 (7)	0.0520 (19)
H3	0.3572	0.1952	0.8454	0.062*
C4	0.5146 (8)	0.0636 (8)	0.7771 (7)	0.0474 (17)
H4	0.4517	0.0330	0.6970	0.057*
C5	0.6679 (9)	0.0167 (7)	0.8124 (7)	0.0499 (18)
H5	0.7080	−0.0438	0.7526	0.060*
C6	0.8075 (8)	0.1806 (7)	1.1455 (6)	0.0480 (18)
H6A	0.8467	0.2827	1.1412	0.058*
H6B	0.7486	0.1773	1.2167	0.058*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Fe1	0.0257 (7)	0.0396 (7)	0.0178 (6)	0.0092 (6)	0.0075 (4)	−0.0027 (6)
O1	0.089 (4)	0.047 (3)	0.036 (3)	−0.013 (3)	0.004 (3)	−0.007 (2)
O2	0.117 (5)	0.064 (3)	0.073 (4)	−0.031 (4)	0.031 (4)	0.012 (3)
O3	0.083 (4)	0.069 (3)	0.032 (3)	−0.010 (3)	0.011 (3)	−0.002 (2)
N1	0.050 (4)	0.045 (3)	0.032 (3)	−0.006 (3)	0.012 (3)	0.000 (2)
N2	0.047 (4)	0.039 (3)	0.048 (3)	0.000 (3)	0.007 (3)	−0.002 (3)
N3	0.049 (4)	0.044 (3)	0.040 (3)	0.006 (3)	0.011 (3)	0.002 (3)
C1	0.053 (5)	0.032 (3)	0.040 (4)	−0.002 (3)	0.012 (3)	−0.005 (3)
C2	0.048 (5)	0.056 (4)	0.051 (4)	0.009 (4)	0.012 (4)	−0.013 (3)
C3	0.050 (5)	0.051 (4)	0.055 (4)	0.006 (4)	0.011 (4)	0.009 (4)
C4	0.046 (5)	0.053 (4)	0.042 (4)	−0.005 (4)	0.006 (4)	0.006 (3)
C5	0.058 (5)	0.050 (4)	0.041 (4)	−0.002 (4)	0.007 (3)	0.004 (3)
C6	0.047 (5)	0.051 (4)	0.046 (4)	0.000 (4)	0.010 (4)	−0.005 (3)

Geometric parameters (Å, º)

Fe1—N2^i	2.076 (5)	N2—H2B	0.90
Fe1—N2	2.076 (5)	C1—C2	1.372 (9)
Fe1—N1^i	2.128 (6)	C1—C6	1.497 (9)
Fe1—N1	2.128 (6)	C2—C3	1.359 (9)
Fe1—O1	2.297 (4)	C2—H2	0.93
Fe1—O1^i	2.297 (4)	C3—C4	1.394 (9)
O1—N3	1.268 (6)	C3—H3	0.93
O2—N3	1.243 (7)	C4—C5	1.387 (9)
O3—N3	1.228 (6)	C4—H4	0.93
N1—C1	1.340 (7)	C5—H5	0.93
N1—C5	1.355 (8)	C6—H6A	0.97
N2—C6	1.486 (8)	C6—H6B	0.97
N2—H2A	0.90
N2^i—Fe1—N2	180.00 (2)	O3—N3—O2	121.0 (6)
N2^i—Fe1—N1^i	79.6 (2)	O3—N3—O1	120.3 (6)
N2—Fe1—N1^i	100.4 (2)	O2—N3—O1	118.7 (5)
N2^i—Fe1—N1	100.4 (2)	N1—C1—C2	121.6 (6)
N2—Fe1—N1	79.6 (2)	N1—C1—C6	117.1 (6)
N1^i—Fe1—N1	180.00 (2)	C2—C1—C6	121.4 (6)
N2^i—Fe1—O1	85.80 (18)	C3—C2—C1	120.9 (6)
N2—Fe1—O1	94.20 (18)	C3—C2—H2	119.6
N1^i—Fe1—O1	91.19 (19)	C1—C2—H2	119.6
N1—Fe1—O1	88.81 (19)	C2—C3—C4	119.0 (7)
N2^i—Fe1—O1^i	94.20 (18)	C2—C3—H3	120.5
N2—Fe1—O1^i	85.80 (18)	C4—C3—H3	120.5
N1^i—Fe1—O1^i	88.81 (19)	C5—C4—C3	117.5 (6)
N1—Fe1—O1^i	91.19 (19)	C5—C4—H4	121.2
O1—Fe1—O1^i	180.0	C3—C4—H4	121.2
N3—O1—Fe1	125.3 (4)	N1—C5—C4	123.1 (7)
C1—N1—C5	117.9 (6)	N1—C5—H5	118.5
C1—N1—Fe1	113.2 (4)	C4—C5—H5	118.5
C5—N1—Fe1	128.8 (5)	N2—C6—C1	111.5 (5)
C6—N2—Fe1	109.6 (4)	N2—C6—H6A	109.3
C6—N2—H2A	109.8	C1—C6—H6A	109.3
Fe1—N2—H2A	109.8	N2—C6—H6B	109.3
C6—N2—H2B	109.8	C1—C6—H6B	109.3
Fe1—N2—H2B	109.8	H6A—C6—H6B	108.0
H2A—N2—H2B	108.2
N2^i—Fe1—O1—N3	−137.6 (5)	Fe1—O1—N3—O3	−18.6 (9)
N2—Fe1—O1—N3	42.4 (5)	Fe1—O1—N3—O2	163.1 (5)
N1^i—Fe1—O1—N3	−58.1 (5)	C5—N1—C1—C2	−1.7 (9)
N1—Fe1—O1—N3	121.9 (5)	Fe1—N1—C1—C2	176.5 (5)
N2^i—Fe1—N1—C1	−163.4 (4)	C5—N1—C1—C6	178.7 (6)
N2—Fe1—N1—C1	16.6 (4)	Fe1—N1—C1—C6	−3.1 (7)
O1—Fe1—N1—C1	−77.9 (4)	N1—C1—C2—C3	1.8 (10)
O1^i—Fe1—N1—C1	102.1 (4)	C6—C1—C2—C3	−178.6 (6)
N2^i—Fe1—N1—C5	14.5 (6)	C1—C2—C3—C4	0.1 (11)
N2—Fe1—N1—C5	−165.5 (6)	C2—C3—C4—C5	−2.0 (10)
O1—Fe1—N1—C5	100.0 (5)	C1—N1—C5—C4	−0.3 (9)
O1^i—Fe1—N1—C5	−80.0 (5)	Fe1—N1—C5—C4	−178.1 (5)
N1^i—Fe1—N2—C6	154.2 (4)	C3—C4—C5—N1	2.1 (10)
N1—Fe1—N2—C6	−25.8 (4)	Fe1—N2—C6—C1	31.6 (6)
O1—Fe1—N2—C6	62.2 (4)	N1—C1—C6—N2	−19.1 (8)
O1^i—Fe1—N2—C6	−117.8 (4)	C2—C1—C6—N2	161.3 (6)

Symmetry code: (i) −x+2, −y, −z+2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2B···O2^ii	0.90	2.65	3.338 (8)	134
N2—H2B···O1^ii	0.90	2.43	3.139 (7)	135
N2—H2B···O3	0.90	2.42	2.976 (7)	120
N2—H2A···O3^iii	0.90	2.24	3.130 (7)	171

Symmetry codes: (ii) x, −y+1/2, z+1/2; (iii) −x+2, y−1/2, −z+5/2.