[1,2-Bis(1H-pyrrol-2-ylmethyl­eneamino)ethane-κ⁴N]iron(II)

In the title compound, [Fe(C₁₂H₁₂N₄)], the metal atom is four-coordinated by four N atoms from the Schiff base ligand in an approximately square-planar configuration. The Fe—N distances are in the range 1.833 (3)–1.876 (3) Å.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.008 Å
• R factor = 0.047
• wR factor = 0.126
• Data-to-parameter ratio = 12.9

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.98
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.97
PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size .......       0.68 mm
PLAT150_ALERT_1_C Volume as Calculated Differs from that Given ...     574.30 Ang-3
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Fe1    -   N1      ..       6.53 su
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Fe1    -   N2      ..       5.87 su
PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          8

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

   3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 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: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXL97.

[1,2-Bis(1H-pyrrol-2-ylmethyleneamino)ethane-κ⁴N]iron(II)

Crystal data

[Fe(C12H12N4)]	Z = 2
Mr = 268.11	F(000) = 276
Triclinic, P1	Dx = 1.550 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.923 (3) Å	Cell parameters from 1886 reflections
b = 8.828 (3) Å	θ = 2.6–27.3°
c = 10.512 (4) Å	µ = 1.29 mm^−1
α = 114.634 (4)°	T = 293 K
β = 92.149 (4)°	Block, brown
γ = 98.351 (4)°	0.68 × 0.52 × 0.33 mm
V = 574.3 (4) Å^3

Data collection

Siemens SMART CCD area-detector diffractometer	1988 independent reflections
Radiation source: fine-focus sealed tube	1740 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.028
φ and ω scans	θmax = 25.0°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −8→7
Tmin = 0.473, Tmax = 0.675	k = −10→10
2960 measured reflections	l = −12→11

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.127	H-atom parameters constrained
S = 1.01	w = 1/[σ^2(Fo^2) + (0.0909P)^2] where P = (Fo^2 + 2Fc^2)/3
1988 reflections	(Δ/σ)max = 0.001
154 parameters	Δρmax = 0.83 e Å^−3
0 restraints	Δρmin = −0.76 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	0.75616 (6)	0.53637 (6)	0.50806 (5)	0.0357 (2)
N1	0.8023 (5)	0.5960 (4)	0.3587 (3)	0.0491 (8)
N2	0.7539 (5)	0.7390 (4)	0.6675 (3)	0.0494 (7)
N3	0.7553 (5)	0.3192 (4)	0.3754 (4)	0.0515 (8)
N4	0.6994 (4)	0.4354 (4)	0.6265 (3)	0.0498 (8)
C1	0.7835 (6)	0.3022 (6)	0.2507 (5)	0.0591 (11)
H1	0.7890	0.1981	0.1770	0.071*
C2	0.8055 (6)	0.4551 (6)	0.2341 (4)	0.0572 (10)
C3	0.8316 (7)	0.4994 (7)	0.1244 (5)	0.0762 (14)
H3	0.8393	0.4276	0.0309	0.091*
C4	0.8440 (7)	0.6751 (7)	0.1828 (5)	0.0774 (14)
H4	0.8611	0.7434	0.1351	0.093*
C5	0.8260 (6)	0.7285 (6)	0.3256 (4)	0.0609 (11)
H5	0.8298	0.8404	0.3894	0.073*
C6	0.6780 (6)	0.5359 (6)	0.7544 (5)	0.0602 (11)
H6	0.6441	0.4968	0.8216	0.072*
C7	0.7104 (6)	0.7101 (6)	0.7840 (4)	0.0577 (10)
C8	0.7018 (8)	0.8602 (7)	0.8977 (5)	0.0827 (15)
H8	0.6729	0.8741	0.9872	0.099*
C9	0.7445 (8)	0.9860 (7)	0.8522 (5)	0.0868 (16)
H9	0.7515	1.1015	0.9058	0.104*
C10	0.7749 (6)	0.9074 (6)	0.7118 (5)	0.0628 (11)
H10	0.8058	0.9637	0.6557	0.075*
C11	0.7418 (6)	0.1863 (5)	0.4251 (5)	0.0623 (11)
H11A	0.8706	0.1588	0.4348	0.075*
H11B	0.6557	0.0847	0.3582	0.075*
C12	0.6615 (6)	0.2507 (5)	0.5646 (5)	0.0642 (11)
H12A	0.5213	0.2089	0.5522	0.077*
H12B	0.7242	0.2113	0.6263	0.077*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Fe1	0.0350 (3)	0.0307 (3)	0.0456 (3)	0.00397 (19)	0.0042 (2)	0.0210 (2)
N1	0.0474 (18)	0.0460 (18)	0.0572 (18)	0.0054 (14)	0.0098 (14)	0.0259 (16)
N2	0.0488 (18)	0.0450 (18)	0.0548 (18)	0.0052 (14)	0.0032 (14)	0.0229 (15)
N3	0.0498 (18)	0.0410 (17)	0.065 (2)	0.0097 (14)	0.0069 (15)	0.0234 (16)
N4	0.0447 (17)	0.0528 (19)	0.062 (2)	0.0066 (14)	0.0025 (14)	0.0353 (17)
C1	0.057 (2)	0.051 (2)	0.059 (2)	0.0071 (19)	0.0095 (19)	0.015 (2)
C2	0.056 (2)	0.057 (3)	0.057 (2)	0.0048 (19)	0.0080 (18)	0.024 (2)
C3	0.085 (3)	0.083 (4)	0.059 (3)	0.002 (3)	0.012 (2)	0.032 (3)
C4	0.088 (3)	0.091 (4)	0.075 (3)	0.007 (3)	0.017 (2)	0.057 (3)
C5	0.062 (3)	0.055 (2)	0.077 (3)	0.008 (2)	0.014 (2)	0.041 (2)
C6	0.054 (2)	0.076 (3)	0.066 (3)	0.007 (2)	0.0057 (19)	0.047 (3)
C7	0.053 (2)	0.067 (3)	0.053 (2)	0.006 (2)	0.0047 (17)	0.027 (2)
C8	0.100 (4)	0.080 (4)	0.052 (2)	0.003 (3)	0.007 (2)	0.016 (3)
C9	0.112 (4)	0.054 (3)	0.069 (3)	0.005 (3)	0.005 (3)	0.005 (3)
C10	0.070 (3)	0.046 (2)	0.069 (3)	0.003 (2)	0.007 (2)	0.024 (2)
C11	0.058 (2)	0.044 (2)	0.089 (3)	0.0081 (19)	0.003 (2)	0.033 (2)
C12	0.061 (3)	0.053 (2)	0.095 (3)	0.012 (2)	0.014 (2)	0.047 (3)

Geometric parameters (Å, º)

Fe1—N4	1.833 (3)	C4—C5	1.390 (6)
Fe1—N3	1.841 (3)	C4—H4	0.93
Fe1—N2	1.876 (3)	C5—H5	0.93
Fe1—N1	1.876 (3)	C6—C7	1.417 (7)
N1—C5	1.343 (5)	C6—H6	0.93
N1—C2	1.384 (6)	C7—C8	1.377 (7)
N2—C10	1.343 (6)	C8—C9	1.381 (8)
N2—C7	1.385 (5)	C8—H8	0.93
N3—C1	1.282 (5)	C9—C10	1.384 (6)
N3—C11	1.463 (5)	C9—H9	0.93
N4—C6	1.294 (6)	C10—H10	0.93
N4—C12	1.459 (6)	C11—C12	1.497 (6)
C1—C2	1.418 (6)	C11—H11A	0.97
C1—H1	0.93	C11—H11B	0.97
C2—C3	1.374 (6)	C12—H12A	0.97
C3—C4	1.397 (8)	C12—H12B	0.97
C3—H3	0.93
N4—Fe1—N3	84.53 (15)	N1—C5—C4	110.6 (4)
N4—Fe1—N2	84.67 (14)	N1—C5—H5	124.7
N3—Fe1—N2	169.07 (13)	C4—C5—H5	124.7
N4—Fe1—N1	168.68 (14)	N4—C6—C7	114.7 (4)
N3—Fe1—N1	84.43 (14)	N4—C6—H6	122.6
N2—Fe1—N1	106.43 (15)	C7—C6—H6	122.6
C5—N1—C2	105.7 (3)	C8—C7—N2	110.5 (4)
C5—N1—Fe1	142.6 (3)	C8—C7—C6	136.6 (4)
C2—N1—Fe1	111.6 (3)	N2—C7—C6	112.8 (4)
C10—N2—C7	105.4 (4)	C7—C8—C9	106.2 (4)
C10—N2—Fe1	142.8 (3)	C7—C8—H8	126.9
C7—N2—Fe1	111.8 (3)	C9—C8—H8	126.9
C1—N3—C11	126.4 (4)	C8—C9—C10	107.0 (5)
C1—N3—Fe1	116.2 (3)	C8—C9—H9	126.5
C11—N3—Fe1	117.1 (3)	C10—C9—H9	126.5
C6—N4—C12	126.4 (4)	N2—C10—C9	110.9 (4)
C6—N4—Fe1	116.0 (3)	N2—C10—H10	124.5
C12—N4—Fe1	117.3 (3)	C9—C10—H10	124.5
N3—C1—C2	114.6 (4)	N3—C11—C12	107.9 (4)
N3—C1—H1	122.7	N3—C11—H11A	110.1
C2—C1—H1	122.7	C12—C11—H11A	110.1
C3—C2—N1	111.1 (4)	N3—C11—H11B	110.1
C3—C2—C1	135.8 (4)	C12—C11—H11B	110.1
N1—C2—C1	113.1 (4)	H11A—C11—H11B	108.4
C2—C3—C4	105.6 (4)	N4—C12—C11	108.6 (3)
C2—C3—H3	127.2	N4—C12—H12A	110.0
C4—C3—H3	127.2	C11—C12—H12A	110.0
C5—C4—C3	107.1 (4)	N4—C12—H12B	110.0
C5—C4—H4	126.5	C11—C12—H12B	110.0
C3—C4—H4	126.5	H12A—C12—H12B	108.4
N4—Fe1—N1—C5	164.8 (6)	Fe1—N1—C2—C1	−3.0 (4)
N3—Fe1—N1—C5	177.6 (5)	N3—C1—C2—C3	−177.7 (5)
N2—Fe1—N1—C5	−3.6 (5)	N3—C1—C2—N1	3.1 (6)
N4—Fe1—N1—C2	−11.1 (7)	N1—C2—C3—C4	−0.3 (5)
N3—Fe1—N1—C2	1.7 (3)	C1—C2—C3—C4	−179.5 (5)
N2—Fe1—N1—C2	−179.5 (3)	C2—C3—C4—C5	0.3 (6)
N4—Fe1—N2—C10	−178.6 (5)	C2—N1—C5—C4	0.1 (5)
N3—Fe1—N2—C10	172.6 (6)	Fe1—N1—C5—C4	−176.0 (4)
N1—Fe1—N2—C10	−0.9 (5)	C3—C4—C5—N1	−0.3 (6)
N4—Fe1—N2—C7	−0.9 (3)	C12—N4—C6—C7	−175.2 (4)
N3—Fe1—N2—C7	−9.7 (8)	Fe1—N4—C6—C7	−2.5 (5)
N1—Fe1—N2—C7	176.8 (3)	C10—N2—C7—C8	1.0 (5)
N4—Fe1—N3—C1	177.5 (3)	Fe1—N2—C7—C8	−177.5 (3)
N2—Fe1—N3—C1	−173.8 (6)	C10—N2—C7—C6	178.4 (4)
N1—Fe1—N3—C1	0.0 (3)	Fe1—N2—C7—C6	−0.1 (4)
N4—Fe1—N3—C11	−8.3 (3)	N4—C6—C7—C8	178.1 (5)
N2—Fe1—N3—C11	0.5 (8)	N4—C6—C7—N2	1.7 (6)
N1—Fe1—N3—C11	174.3 (3)	N2—C7—C8—C9	−1.1 (6)
N3—Fe1—N4—C6	−179.7 (3)	C6—C7—C8—C9	−177.7 (5)
N2—Fe1—N4—C6	2.0 (3)	C7—C8—C9—C10	0.8 (6)
N1—Fe1—N4—C6	−166.8 (5)	C7—N2—C10—C9	−0.5 (5)
N3—Fe1—N4—C12	−6.3 (3)	Fe1—N2—C10—C9	177.3 (3)
N2—Fe1—N4—C12	175.4 (3)	C8—C9—C10—N2	−0.2 (6)
N1—Fe1—N4—C12	6.5 (8)	C1—N3—C11—C12	−166.7 (4)
C11—N3—C1—C2	−175.4 (4)	Fe1—N3—C11—C12	19.7 (4)
Fe1—N3—C1—C2	−1.7 (5)	C6—N4—C12—C11	−169.1 (4)
C5—N1—C2—C3	0.2 (5)	Fe1—N4—C12—C11	18.3 (4)
Fe1—N1—C2—C3	177.6 (3)	N3—C11—C12—N4	−22.6 (5)
C5—N1—C2—C1	179.6 (4)