Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807029601/om2132sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807029601/om2132Isup2.hkl |
CCDC reference: 654799
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.010 Å
- R factor = 0.054
- wR factor = 0.170
- Data-to-parameter ratio = 13.7
checkCIF/PLATON results
No syntax errors found
Alert level C GOODF01_ALERT_2_C The least squares goodness of fit parameter lies outside the range 0.80 <> 2.00 Goodness of fit given = 0.689 PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for O2 PLAT341_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 10 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 44 O2 -FE1 -N1 -C7 -33.00 6.00 1.555 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 47 O2 -FE1 -N1 -C6 142.00 6.00 1.555 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 57 O1 -FE1 -N2 -C20 -14.00 18.00 1.555 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 60 O1 -FE1 -N2 -C1 17.00 0.00 1.555 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 65 N2 -FE1 -O1 -C13 18.00 0.00 1.555 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 71 N1 -FE1 -O2 -C14 -132.00 6.00 1.555 1.555 1.555 1.555
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 26.00 From the CIF: _reflns_number_total 3106 Count of symmetry unique reflns 1827 Completeness (_total/calc) 170.01% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 1279 Fraction of Friedel pairs measured 0.700 Are heavy atom types Z>Si present yes PLAT794_ALERT_5_G Check Predicted Bond Valency for Fe1 (3) 3.38
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 9 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 0 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 1 ALERT type 3 Indicator that the structure quality may be low 7 ALERT type 4 Improvement, methodology, query or suggestion 1 ALERT type 5 Informative message, check
For related literature, see: Liu et al. (2004); You & Zhu (2004); You et al. (2004, 2005); Zhu et al. (2003).
All the solvents and chemicals were used as bought from Shanghai Chmical Company, Shanghai China, without further purification. 1,2-diaminobenzene and two equivalents of salicylaldehyde were dissolved in acetonitrile at room temperature with stirring. Five minutes later, equimolar Fe(ClO4)2·6H2O in methanol was added to the above solution, giving a clear dark green solution. Large green crystals precipitated after the solution was stood still in air for three days. These crystals were filtered, washed with acetonitrile/methanol (v:v = 1:1) for three times, and dried in air. Yield: 93%.
When using FeCl2·4H2O, Fe(NO3)2·6H2O, FeSO4·7H2O, or Fe(CH3COO)2·2H2O replaced Fe(ClO4)2·6H2O in the above reaction, the same product was isolated with the yields 65%, 46%, 70%, and 41%, respectively.
C-bound H atoms were included in the riding model approximation with C—H = 0.93–0.97 Å, and with Uiso(H) = 1.2Ueq(C).
Because of their interesting physical and biological properties, many iron complexes with amines or imines have structurally been studied (Liu, et al. 2004, You, et al. 2004a, 2004b, You, et al. 2005, Zhu, 2003a). When trying to synthesize iron(II) complexes with a Schiff base, condensed from salicylaldehyde and N-1,2-diaminobenzene, we isolated the title Fe(II) complex.
The title complex is a discrete iron(II) complex. The central iron(II) atom is four-coordinated by two oxygen atoms and two nitrogen atoms from a Schiff base ligand. The Schiff base acts as a tetradentate ligand. The iron(II) atom is in a distorted planar square coordination geometry.
Interestingly, all the atoms, including the hydrogen atoms, are in a plane with the mean deviation of 0.100 (2) /%A.
For related literature, see: Liu et al. (2004); You & Zhu (2004); You et al. (2004, 2005); Zhu et al. (2003).
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: SHELXTL.
Fig. 1. The molecular structure of (I), showing 30% probability displacement ellipsoids and the atom-numbering scheme. |
Fe(C20H14N2O2)] | F(000) = 760 |
Mr = 370.18 | Dx = 1.564 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 1882 reflections |
a = 5.4675 (10) Å | θ = 2.2–24.8° |
b = 16.616 (4) Å | µ = 0.98 mm−1 |
c = 17.310 (3) Å | T = 298 K |
V = 1572.6 (5) Å3 | Block, green |
Z = 4 | 0.30 × 0.20 × 0.20 mm |
Bruker APEX area-detector diffractometer | 3106 independent reflections |
Radiation source: fine-focus sealed tube | 2404 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.069 |
φ and ω scans | θmax = 26.0°, θmin = 1.7° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −6→6 |
Tmin = 0.759, Tmax = 0.829 | k = −20→20 |
11948 measured reflections | l = −21→21 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.054 | H-atom parameters constrained |
wR(F2) = 0.170 | w = 1/[σ2(Fo2) + (0.1483P)2 + 4.4994P] where P = (Fo2 + 2Fc2)/3 |
S = 0.69 | (Δ/σ)max = 0.003 |
3106 reflections | Δρmax = 0.45 e Å−3 |
226 parameters | Δρmin = −0.27 e Å−3 |
0 restraints | Absolute structure: Flack (1983), 1279 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: −0.09 (4) |
Fe(C20H14N2O2)] | V = 1572.6 (5) Å3 |
Mr = 370.18 | Z = 4 |
Orthorhombic, P212121 | Mo Kα radiation |
a = 5.4675 (10) Å | µ = 0.98 mm−1 |
b = 16.616 (4) Å | T = 298 K |
c = 17.310 (3) Å | 0.30 × 0.20 × 0.20 mm |
Bruker APEX area-detector diffractometer | 3106 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 2404 reflections with I > 2σ(I) |
Tmin = 0.759, Tmax = 0.829 | Rint = 0.069 |
11948 measured reflections |
R[F2 > 2σ(F2)] = 0.054 | H-atom parameters constrained |
wR(F2) = 0.170 | Δρmax = 0.45 e Å−3 |
S = 0.69 | Δρmin = −0.27 e Å−3 |
3106 reflections | Absolute structure: Flack (1983), 1279 Friedel pairs |
226 parameters | Absolute structure parameter: −0.09 (4) |
0 restraints |
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. |
x | y | z | Uiso*/Ueq | ||
C1 | 1.1934 (12) | 0.3423 (4) | 0.1633 (4) | 0.0426 (15) | |
C2 | 1.3846 (14) | 0.3878 (4) | 0.1349 (4) | 0.0521 (17) | |
H2 | 1.4875 | 0.3673 | 0.0969 | 0.063* | |
C3 | 1.4207 (15) | 0.4650 (4) | 0.1642 (4) | 0.060 (2) | |
H3 | 1.5508 | 0.4958 | 0.1462 | 0.072* | |
C4 | 1.2652 (16) | 0.4965 (4) | 0.2199 (4) | 0.060 (2) | |
H4 | 1.2917 | 0.5481 | 0.2390 | 0.072* | |
C5 | 1.0714 (14) | 0.4514 (4) | 0.2471 (4) | 0.0541 (18) | |
H5 | 0.9652 | 0.4730 | 0.2836 | 0.065* | |
C6 | 1.0350 (13) | 0.3734 (4) | 0.2197 (4) | 0.0453 (15) | |
C7 | 0.7082 (12) | 0.3363 (4) | 0.3033 (4) | 0.0490 (16) | |
H7 | 0.7374 | 0.3846 | 0.3289 | 0.059* | |
C8 | 0.5157 (12) | 0.2872 (4) | 0.3314 (4) | 0.0488 (16) | |
C9 | 0.3786 (15) | 0.3146 (5) | 0.3949 (4) | 0.0571 (18) | |
H9 | 0.4183 | 0.3635 | 0.4180 | 0.069* | |
C10 | 0.1874 (14) | 0.2704 (5) | 0.4231 (4) | 0.067 (2) | |
H10 | 0.1015 | 0.2882 | 0.4662 | 0.080* | |
C11 | 0.1221 (15) | 0.1991 (5) | 0.3876 (5) | 0.062 (2) | |
H11 | −0.0125 | 0.1705 | 0.4057 | 0.075* | |
C12 | 0.2531 (14) | 0.1696 (5) | 0.3256 (4) | 0.0567 (19) | |
H12 | 0.2087 | 0.1210 | 0.3031 | 0.068* | |
C13 | 0.4562 (12) | 0.2135 (4) | 0.2962 (3) | 0.0443 (15) | |
C14 | 1.0161 (12) | 0.0988 (4) | 0.0916 (4) | 0.0430 (14) | |
C15 | 0.9921 (14) | 0.0188 (4) | 0.0622 (4) | 0.0526 (17) | |
H15 | 0.8568 | −0.0117 | 0.0764 | 0.063* | |
C16 | 1.1597 (16) | −0.0137 (4) | 0.0145 (4) | 0.0582 (18) | |
H16 | 1.1385 | −0.0664 | −0.0023 | 0.070* | |
C17 | 1.3645 (16) | 0.0293 (4) | −0.0106 (4) | 0.0609 (19) | |
H17 | 1.4765 | 0.0065 | −0.0445 | 0.073* | |
C18 | 1.3949 (14) | 0.1061 (4) | 0.0164 (4) | 0.0556 (18) | |
H18 | 1.5315 | 0.1353 | 0.0010 | 0.067* | |
C19 | 1.2225 (12) | 0.1426 (4) | 0.0677 (4) | 0.0479 (16) | |
C20 | 1.2689 (12) | 0.2227 (5) | 0.0936 (4) | 0.0472 (14) | |
H20 | 1.4090 | 0.2482 | 0.0755 | 0.057* | |
Fe1 | 0.85107 (14) | 0.22313 (5) | 0.18970 (4) | 0.0326 (2) | |
N1 | 0.8475 (11) | 0.3190 (3) | 0.2446 (3) | 0.0423 (12) | |
N2 | 1.1281 (10) | 0.2625 (3) | 0.1408 (3) | 0.0402 (11) | |
O1 | 0.5742 (9) | 0.1826 (3) | 0.2377 (3) | 0.0512 (12) | |
O2 | 0.8516 (10) | 0.1260 (3) | 0.1390 (3) | 0.0559 (12) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.050 (4) | 0.040 (3) | 0.037 (3) | 0.000 (3) | −0.006 (3) | 0.005 (3) |
C2 | 0.059 (4) | 0.047 (4) | 0.050 (4) | −0.006 (3) | 0.000 (3) | 0.000 (3) |
C3 | 0.075 (5) | 0.052 (4) | 0.054 (4) | −0.014 (4) | 0.001 (4) | −0.001 (3) |
C4 | 0.081 (5) | 0.048 (4) | 0.051 (4) | −0.013 (4) | 0.002 (4) | −0.008 (3) |
C5 | 0.059 (5) | 0.049 (4) | 0.055 (4) | 0.002 (3) | 0.006 (3) | −0.007 (3) |
C6 | 0.049 (4) | 0.041 (3) | 0.046 (3) | −0.003 (3) | −0.007 (3) | 0.002 (3) |
C7 | 0.058 (4) | 0.050 (3) | 0.039 (3) | 0.007 (3) | −0.001 (3) | −0.004 (3) |
C8 | 0.049 (4) | 0.053 (4) | 0.044 (3) | 0.006 (3) | 0.001 (3) | 0.007 (3) |
C9 | 0.066 (5) | 0.054 (4) | 0.051 (4) | 0.009 (4) | 0.010 (4) | −0.003 (3) |
C10 | 0.068 (5) | 0.081 (6) | 0.051 (4) | 0.020 (5) | 0.016 (4) | 0.007 (4) |
C11 | 0.049 (4) | 0.068 (5) | 0.069 (5) | 0.009 (4) | 0.014 (4) | 0.015 (4) |
C12 | 0.048 (4) | 0.058 (4) | 0.064 (5) | 0.006 (3) | 0.001 (3) | 0.007 (4) |
C13 | 0.041 (3) | 0.045 (3) | 0.047 (4) | 0.011 (3) | 0.002 (3) | 0.008 (3) |
C14 | 0.044 (4) | 0.049 (4) | 0.036 (3) | 0.002 (3) | 0.001 (3) | −0.003 (3) |
C15 | 0.069 (5) | 0.043 (3) | 0.046 (4) | −0.005 (3) | 0.004 (4) | −0.003 (3) |
C16 | 0.080 (5) | 0.044 (3) | 0.051 (4) | 0.014 (4) | −0.005 (4) | −0.005 (3) |
C17 | 0.069 (5) | 0.060 (4) | 0.054 (4) | 0.018 (4) | 0.011 (4) | −0.009 (3) |
C18 | 0.056 (5) | 0.057 (4) | 0.054 (4) | 0.002 (3) | 0.000 (3) | −0.012 (3) |
C19 | 0.046 (4) | 0.058 (4) | 0.040 (3) | 0.002 (3) | −0.003 (3) | 0.001 (3) |
C20 | 0.042 (3) | 0.055 (4) | 0.044 (3) | −0.006 (3) | −0.001 (3) | −0.002 (3) |
Fe1 | 0.0365 (4) | 0.0296 (4) | 0.0318 (4) | 0.0026 (4) | 0.0019 (4) | 0.0010 (3) |
N1 | 0.047 (3) | 0.040 (3) | 0.040 (3) | 0.010 (3) | −0.001 (3) | 0.001 (2) |
N2 | 0.042 (3) | 0.042 (3) | 0.037 (2) | −0.002 (2) | 0.000 (2) | 0.003 (2) |
O1 | 0.050 (3) | 0.046 (2) | 0.057 (3) | −0.002 (2) | 0.006 (2) | −0.001 (2) |
O2 | 0.060 (3) | 0.046 (2) | 0.061 (3) | −0.008 (3) | 0.013 (3) | −0.009 (2) |
C1—C2 | 1.381 (9) | C11—H11 | 0.9300 |
C1—C6 | 1.403 (9) | C12—C13 | 1.423 (10) |
C1—N2 | 1.427 (8) | C12—H12 | 0.9300 |
C2—C3 | 1.394 (10) | C13—O1 | 1.306 (7) |
C2—H2 | 0.9300 | C14—O2 | 1.299 (7) |
C3—C4 | 1.388 (11) | C14—C19 | 1.405 (9) |
C3—H3 | 0.9300 | C14—C15 | 1.429 (9) |
C4—C5 | 1.381 (10) | C15—C16 | 1.346 (10) |
C4—H4 | 0.9300 | C15—H15 | 0.9300 |
C5—C6 | 1.395 (9) | C16—C17 | 1.398 (11) |
C5—H5 | 0.9300 | C16—H16 | 0.9300 |
C6—N1 | 1.433 (8) | C17—C18 | 1.368 (10) |
C7—N1 | 1.302 (8) | C17—H17 | 0.9300 |
C7—C8 | 1.417 (9) | C18—C19 | 1.429 (9) |
C7—H7 | 0.9300 | C18—H18 | 0.9300 |
C8—C13 | 1.406 (9) | C19—C20 | 1.428 (10) |
C8—C9 | 1.406 (9) | C20—N2 | 1.303 (8) |
C9—C10 | 1.368 (11) | C20—H20 | 0.9300 |
C9—H9 | 0.9300 | Fe1—O2 | 1.838 (4) |
C10—C11 | 1.382 (12) | Fe1—O1 | 1.854 (5) |
C10—H10 | 0.9300 | Fe1—N2 | 1.855 (5) |
C11—C12 | 1.379 (10) | Fe1—N1 | 1.856 (5) |
C2—C1—C6 | 121.0 (6) | O1—C13—C12 | 117.5 (6) |
C2—C1—N2 | 126.9 (6) | C8—C13—C12 | 118.1 (6) |
C6—C1—N2 | 112.1 (6) | O2—C14—C19 | 124.2 (6) |
C1—C2—C3 | 118.8 (7) | O2—C14—C15 | 119.0 (6) |
C1—C2—H2 | 120.6 | C19—C14—C15 | 116.8 (6) |
C3—C2—H2 | 120.6 | C16—C15—C14 | 121.9 (7) |
C4—C3—C2 | 120.9 (7) | C16—C15—H15 | 119.0 |
C4—C3—H3 | 119.5 | C14—C15—H15 | 119.0 |
C2—C3—H3 | 119.5 | C15—C16—C17 | 122.0 (7) |
C5—C4—C3 | 120.1 (7) | C15—C16—H16 | 119.0 |
C5—C4—H4 | 119.9 | C17—C16—H16 | 119.0 |
C3—C4—H4 | 119.9 | C18—C17—C16 | 117.9 (7) |
C4—C5—C6 | 119.9 (7) | C18—C17—H17 | 121.0 |
C4—C5—H5 | 120.1 | C16—C17—H17 | 121.0 |
C6—C5—H5 | 120.1 | C17—C18—C19 | 121.8 (7) |
C5—C6—C1 | 119.4 (6) | C17—C18—H18 | 119.1 |
C5—C6—N1 | 125.8 (6) | C19—C18—H18 | 119.1 |
C1—C6—N1 | 114.8 (5) | C14—C19—C20 | 122.2 (6) |
N1—C7—C8 | 125.1 (6) | C14—C19—C18 | 119.5 (6) |
N1—C7—H7 | 117.4 | C20—C19—C18 | 118.3 (6) |
C8—C7—H7 | 117.4 | N2—C20—C19 | 124.5 (6) |
C13—C8—C9 | 119.9 (6) | N2—C20—H20 | 117.8 |
C13—C8—C7 | 121.6 (6) | C19—C20—H20 | 117.8 |
C9—C8—C7 | 118.5 (7) | O2—Fe1—O1 | 84.0 (2) |
C10—C9—C8 | 120.8 (7) | O2—Fe1—N2 | 95.2 (2) |
C10—C9—H9 | 119.6 | O1—Fe1—N2 | 179.2 (2) |
C8—C9—H9 | 119.6 | O2—Fe1—N1 | 177.7 (2) |
C9—C10—C11 | 120.0 (7) | O1—Fe1—N1 | 94.2 (2) |
C9—C10—H10 | 120.0 | N2—Fe1—N1 | 86.5 (2) |
C11—C10—H10 | 120.0 | C7—N1—C6 | 121.0 (5) |
C12—C11—C10 | 121.1 (8) | C7—N1—Fe1 | 126.5 (5) |
C12—C11—H11 | 119.5 | C6—N1—Fe1 | 112.3 (4) |
C10—C11—H11 | 119.5 | C20—N2—C1 | 119.7 (6) |
C11—C12—C13 | 120.1 (7) | C20—N2—Fe1 | 126.1 (4) |
C11—C12—H12 | 119.9 | C1—N2—Fe1 | 114.1 (4) |
C13—C12—H12 | 119.9 | C13—O1—Fe1 | 127.4 (4) |
O1—C13—C8 | 124.4 (6) | C14—O2—Fe1 | 127.5 (4) |
C6—C1—C2—C3 | 1.1 (10) | C18—C19—C20—N2 | −179.3 (6) |
N2—C1—C2—C3 | −179.8 (6) | C8—C7—N1—C6 | 178.8 (6) |
C1—C2—C3—C4 | −1.2 (11) | C8—C7—N1—Fe1 | −6.6 (9) |
C2—C3—C4—C5 | 0.0 (12) | C5—C6—N1—C7 | −8.0 (10) |
C3—C4—C5—C6 | 1.4 (12) | C1—C6—N1—C7 | 171.2 (6) |
C4—C5—C6—C1 | −1.5 (10) | C5—C6—N1—Fe1 | 176.7 (6) |
C4—C5—C6—N1 | 177.7 (6) | C1—C6—N1—Fe1 | −4.1 (7) |
C2—C1—C6—C5 | 0.2 (10) | O2—Fe1—N1—C7 | −33 (6) |
N2—C1—C6—C5 | −179.0 (6) | O1—Fe1—N1—C7 | 9.0 (5) |
C2—C1—C6—N1 | −179.0 (5) | N2—Fe1—N1—C7 | −171.1 (5) |
N2—C1—C6—N1 | 1.7 (8) | O2—Fe1—N1—C6 | 142 (6) |
N1—C7—C8—C13 | −0.6 (10) | O1—Fe1—N1—C6 | −176.0 (4) |
N1—C7—C8—C9 | −179.1 (6) | N2—Fe1—N1—C6 | 3.9 (4) |
C13—C8—C9—C10 | 0.1 (10) | C19—C20—N2—C1 | 179.6 (6) |
C7—C8—C9—C10 | 178.6 (6) | C19—C20—N2—Fe1 | 4.2 (9) |
C8—C9—C10—C11 | −2.1 (11) | C2—C1—N2—C20 | 6.4 (9) |
C9—C10—C11—C12 | 2.8 (12) | C6—C1—N2—C20 | −174.4 (6) |
C10—C11—C12—C13 | −1.4 (11) | C2—C1—N2—Fe1 | −177.7 (5) |
C9—C8—C13—O1 | −179.1 (6) | C6—C1—N2—Fe1 | 1.5 (6) |
C7—C8—C13—O1 | 2.5 (10) | O2—Fe1—N2—C20 | −6.0 (5) |
C9—C8—C13—C12 | 1.3 (9) | O1—Fe1—N2—C20 | −14 (18) |
C7—C8—C13—C12 | −177.1 (6) | N1—Fe1—N2—C20 | 172.5 (5) |
C11—C12—C13—O1 | 179.7 (6) | O2—Fe1—N2—C1 | 178.5 (4) |
C11—C12—C13—C8 | −0.7 (10) | O1—Fe1—N2—C1 | 170 (67) |
O2—C14—C15—C16 | −178.2 (6) | N1—Fe1—N2—C1 | −3.1 (4) |
C19—C14—C15—C16 | 0.6 (10) | C8—C13—O1—Fe1 | 3.1 (9) |
C14—C15—C16—C17 | −1.4 (11) | C12—C13—O1—Fe1 | −177.3 (5) |
C15—C16—C17—C18 | 1.6 (12) | O2—Fe1—O1—C13 | 171.0 (5) |
C16—C17—C18—C19 | −1.0 (12) | N2—Fe1—O1—C13 | 179 (100) |
O2—C14—C19—C20 | −0.6 (10) | N1—Fe1—O1—C13 | −7.4 (5) |
C15—C14—C19—C20 | −179.3 (6) | C19—C14—O2—Fe1 | −3.3 (9) |
O2—C14—C19—C18 | 178.7 (6) | C15—C14—O2—Fe1 | 175.5 (5) |
C15—C14—C19—C18 | 0.0 (9) | O1—Fe1—O2—C14 | −174.6 (6) |
C17—C18—C19—C14 | 0.3 (11) | N2—Fe1—O2—C14 | 5.6 (6) |
C17—C18—C19—C20 | 179.6 (7) | N1—Fe1—O2—C14 | −132 (6) |
C14—C19—C20—N2 | 0.0 (10) |
Experimental details
Crystal data | |
Chemical formula | Fe(C20H14N2O2)] |
Mr | 370.18 |
Crystal system, space group | Orthorhombic, P212121 |
Temperature (K) | 298 |
a, b, c (Å) | 5.4675 (10), 16.616 (4), 17.310 (3) |
V (Å3) | 1572.6 (5) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.98 |
Crystal size (mm) | 0.30 × 0.20 × 0.20 |
Data collection | |
Diffractometer | Bruker APEX area-detector |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.759, 0.829 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 11948, 3106, 2404 |
Rint | 0.069 |
(sin θ/λ)max (Å−1) | 0.617 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.054, 0.170, 0.69 |
No. of reflections | 3106 |
No. of parameters | 226 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.45, −0.27 |
Absolute structure | Flack (1983), 1279 Friedel pairs |
Absolute structure parameter | −0.09 (4) |
Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SAINT, SHELXS97 (Sheldrick, 1997a), SHELXL97 (Sheldrick, 1997a), SHELXTL (Sheldrick, 1997b), SHELXTL.
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Because of their interesting physical and biological properties, many iron complexes with amines or imines have structurally been studied (Liu, et al. 2004, You, et al. 2004a, 2004b, You, et al. 2005, Zhu, 2003a). When trying to synthesize iron(II) complexes with a Schiff base, condensed from salicylaldehyde and N-1,2-diaminobenzene, we isolated the title Fe(II) complex.
The title complex is a discrete iron(II) complex. The central iron(II) atom is four-coordinated by two oxygen atoms and two nitrogen atoms from a Schiff base ligand. The Schiff base acts as a tetradentate ligand. The iron(II) atom is in a distorted planar square coordination geometry.
Interestingly, all the atoms, including the hydrogen atoms, are in a plane with the mean deviation of 0.100 (2) /%A.