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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.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806037871/ci2167sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806037871/ci2167Isup2.hkl
Contains datablock I

CCDC reference: 624175

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

Computing details top

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) top
Crystal data top
[Fe(C12H12N4)]Z = 2
Mr = 268.11F(000) = 276
Triclinic, P1Dx = 1.550 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 6.923 (3) ÅCell parameters from 1886 reflections
b = 8.828 (3) Åθ = 2.6–27.3°
c = 10.512 (4) ŵ = 1.29 mm1
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) Å3
Data collection top
Siemens SMART CCD area-detector
diffractometer
1988 independent reflections
Radiation source: fine-focus sealed tube1740 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.028
φ and ω scansθmax = 25.0°, θmin = 2.6°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 87
Tmin = 0.473, Tmax = 0.675k = 1010
2960 measured reflectionsl = 1211
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.047Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.127H-atom parameters constrained
S = 1.01 w = 1/[σ2(Fo2) + (0.0909P)2]
where P = (Fo2 + 2Fc2)/3
1988 reflections(Δ/σ)max = 0.001
154 parametersΔρmax = 0.83 e Å3
0 restraintsΔρmin = 0.76 e Å3
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
xyzUiso*/Ueq
Fe10.75616 (6)0.53637 (6)0.50806 (5)0.0357 (2)
N10.8023 (5)0.5960 (4)0.3587 (3)0.0491 (8)
N20.7539 (5)0.7390 (4)0.6675 (3)0.0494 (7)
N30.7553 (5)0.3192 (4)0.3754 (4)0.0515 (8)
N40.6994 (4)0.4354 (4)0.6265 (3)0.0498 (8)
C10.7835 (6)0.3022 (6)0.2507 (5)0.0591 (11)
H10.78900.19810.17700.071*
C20.8055 (6)0.4551 (6)0.2341 (4)0.0572 (10)
C30.8316 (7)0.4994 (7)0.1244 (5)0.0762 (14)
H30.83930.42760.03090.091*
C40.8440 (7)0.6751 (7)0.1828 (5)0.0774 (14)
H40.86110.74340.13510.093*
C50.8260 (6)0.7285 (6)0.3256 (4)0.0609 (11)
H50.82980.84040.38940.073*
C60.6780 (6)0.5359 (6)0.7544 (5)0.0602 (11)
H60.64410.49680.82160.072*
C70.7104 (6)0.7101 (6)0.7840 (4)0.0577 (10)
C80.7018 (8)0.8602 (7)0.8977 (5)0.0827 (15)
H80.67290.87410.98720.099*
C90.7445 (8)0.9860 (7)0.8522 (5)0.0868 (16)
H90.75151.10150.90580.104*
C100.7749 (6)0.9074 (6)0.7118 (5)0.0628 (11)
H100.80580.96370.65570.075*
C110.7418 (6)0.1863 (5)0.4251 (5)0.0623 (11)
H11A0.87060.15880.43480.075*
H11B0.65570.08470.35820.075*
C120.6615 (6)0.2507 (5)0.5646 (5)0.0642 (11)
H12A0.52130.20890.55220.077*
H12B0.72420.21130.62630.077*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Fe10.0350 (3)0.0307 (3)0.0456 (3)0.00397 (19)0.0042 (2)0.0210 (2)
N10.0474 (18)0.0460 (18)0.0572 (18)0.0054 (14)0.0098 (14)0.0259 (16)
N20.0488 (18)0.0450 (18)0.0548 (18)0.0052 (14)0.0032 (14)0.0229 (15)
N30.0498 (18)0.0410 (17)0.065 (2)0.0097 (14)0.0069 (15)0.0234 (16)
N40.0447 (17)0.0528 (19)0.062 (2)0.0066 (14)0.0025 (14)0.0353 (17)
C10.057 (2)0.051 (2)0.059 (2)0.0071 (19)0.0095 (19)0.015 (2)
C20.056 (2)0.057 (3)0.057 (2)0.0048 (19)0.0080 (18)0.024 (2)
C30.085 (3)0.083 (4)0.059 (3)0.002 (3)0.012 (2)0.032 (3)
C40.088 (3)0.091 (4)0.075 (3)0.007 (3)0.017 (2)0.057 (3)
C50.062 (3)0.055 (2)0.077 (3)0.008 (2)0.014 (2)0.041 (2)
C60.054 (2)0.076 (3)0.066 (3)0.007 (2)0.0057 (19)0.047 (3)
C70.053 (2)0.067 (3)0.053 (2)0.006 (2)0.0047 (17)0.027 (2)
C80.100 (4)0.080 (4)0.052 (2)0.003 (3)0.007 (2)0.016 (3)
C90.112 (4)0.054 (3)0.069 (3)0.005 (3)0.005 (3)0.005 (3)
C100.070 (3)0.046 (2)0.069 (3)0.003 (2)0.007 (2)0.024 (2)
C110.058 (2)0.044 (2)0.089 (3)0.0081 (19)0.003 (2)0.033 (2)
C120.061 (3)0.053 (2)0.095 (3)0.012 (2)0.014 (2)0.047 (3)
Geometric parameters (Å, º) top
Fe1—N41.833 (3)C4—C51.390 (6)
Fe1—N31.841 (3)C4—H40.93
Fe1—N21.876 (3)C5—H50.93
Fe1—N11.876 (3)C6—C71.417 (7)
N1—C51.343 (5)C6—H60.93
N1—C21.384 (6)C7—C81.377 (7)
N2—C101.343 (6)C8—C91.381 (8)
N2—C71.385 (5)C8—H80.93
N3—C11.282 (5)C9—C101.384 (6)
N3—C111.463 (5)C9—H90.93
N4—C61.294 (6)C10—H100.93
N4—C121.459 (6)C11—C121.497 (6)
C1—C21.418 (6)C11—H11A0.97
C1—H10.93C11—H11B0.97
C2—C31.374 (6)C12—H12A0.97
C3—C41.397 (8)C12—H12B0.97
C3—H30.93
N4—Fe1—N384.53 (15)N1—C5—C4110.6 (4)
N4—Fe1—N284.67 (14)N1—C5—H5124.7
N3—Fe1—N2169.07 (13)C4—C5—H5124.7
N4—Fe1—N1168.68 (14)N4—C6—C7114.7 (4)
N3—Fe1—N184.43 (14)N4—C6—H6122.6
N2—Fe1—N1106.43 (15)C7—C6—H6122.6
C5—N1—C2105.7 (3)C8—C7—N2110.5 (4)
C5—N1—Fe1142.6 (3)C8—C7—C6136.6 (4)
C2—N1—Fe1111.6 (3)N2—C7—C6112.8 (4)
C10—N2—C7105.4 (4)C7—C8—C9106.2 (4)
C10—N2—Fe1142.8 (3)C7—C8—H8126.9
C7—N2—Fe1111.8 (3)C9—C8—H8126.9
C1—N3—C11126.4 (4)C8—C9—C10107.0 (5)
C1—N3—Fe1116.2 (3)C8—C9—H9126.5
C11—N3—Fe1117.1 (3)C10—C9—H9126.5
C6—N4—C12126.4 (4)N2—C10—C9110.9 (4)
C6—N4—Fe1116.0 (3)N2—C10—H10124.5
C12—N4—Fe1117.3 (3)C9—C10—H10124.5
N3—C1—C2114.6 (4)N3—C11—C12107.9 (4)
N3—C1—H1122.7N3—C11—H11A110.1
C2—C1—H1122.7C12—C11—H11A110.1
C3—C2—N1111.1 (4)N3—C11—H11B110.1
C3—C2—C1135.8 (4)C12—C11—H11B110.1
N1—C2—C1113.1 (4)H11A—C11—H11B108.4
C2—C3—C4105.6 (4)N4—C12—C11108.6 (3)
C2—C3—H3127.2N4—C12—H12A110.0
C4—C3—H3127.2C11—C12—H12A110.0
C5—C4—C3107.1 (4)N4—C12—H12B110.0
C5—C4—H4126.5C11—C12—H12B110.0
C3—C4—H4126.5H12A—C12—H12B108.4
N4—Fe1—N1—C5164.8 (6)Fe1—N1—C2—C13.0 (4)
N3—Fe1—N1—C5177.6 (5)N3—C1—C2—C3177.7 (5)
N2—Fe1—N1—C53.6 (5)N3—C1—C2—N13.1 (6)
N4—Fe1—N1—C211.1 (7)N1—C2—C3—C40.3 (5)
N3—Fe1—N1—C21.7 (3)C1—C2—C3—C4179.5 (5)
N2—Fe1—N1—C2179.5 (3)C2—C3—C4—C50.3 (6)
N4—Fe1—N2—C10178.6 (5)C2—N1—C5—C40.1 (5)
N3—Fe1—N2—C10172.6 (6)Fe1—N1—C5—C4176.0 (4)
N1—Fe1—N2—C100.9 (5)C3—C4—C5—N10.3 (6)
N4—Fe1—N2—C70.9 (3)C12—N4—C6—C7175.2 (4)
N3—Fe1—N2—C79.7 (8)Fe1—N4—C6—C72.5 (5)
N1—Fe1—N2—C7176.8 (3)C10—N2—C7—C81.0 (5)
N4—Fe1—N3—C1177.5 (3)Fe1—N2—C7—C8177.5 (3)
N2—Fe1—N3—C1173.8 (6)C10—N2—C7—C6178.4 (4)
N1—Fe1—N3—C10.0 (3)Fe1—N2—C7—C60.1 (4)
N4—Fe1—N3—C118.3 (3)N4—C6—C7—C8178.1 (5)
N2—Fe1—N3—C110.5 (8)N4—C6—C7—N21.7 (6)
N1—Fe1—N3—C11174.3 (3)N2—C7—C8—C91.1 (6)
N3—Fe1—N4—C6179.7 (3)C6—C7—C8—C9177.7 (5)
N2—Fe1—N4—C62.0 (3)C7—C8—C9—C100.8 (6)
N1—Fe1—N4—C6166.8 (5)C7—N2—C10—C90.5 (5)
N3—Fe1—N4—C126.3 (3)Fe1—N2—C10—C9177.3 (3)
N2—Fe1—N4—C12175.4 (3)C8—C9—C10—N20.2 (6)
N1—Fe1—N4—C126.5 (8)C1—N3—C11—C12166.7 (4)
C11—N3—C1—C2175.4 (4)Fe1—N3—C11—C1219.7 (4)
Fe1—N3—C1—C21.7 (5)C6—N4—C12—C11169.1 (4)
C5—N1—C2—C30.2 (5)Fe1—N4—C12—C1118.3 (4)
Fe1—N1—C2—C3177.6 (3)N3—C11—C12—N422.6 (5)
C5—N1—C2—C1179.6 (4)
 

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