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The title compound {systematic name: bis­[2-(tert-butylimino­meth­yl)phenolato-κ2N,O]iron(II)}, [Fe(C11H14NO)2], was synthesized by the reaction of tetra­kis(trimethyl­phos­phine)iron(0) and N-tert-butyl­salicylaldimine in pentane. The FeII atom exhibits a distorted tetra­hedral coordination geometry.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806051464/bi2102sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806051464/bi2102Isup2.hkl
Contains datablock I

CCDC reference: 633608

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.040
  • wR factor = 0.105
  • Data-to-parameter ratio = 17.0

checkCIF/PLATON results

No syntax errors found



Alert level A PLAT220_ALERT_2_A Large Non-Solvent C Ueq(max)/Ueq(min) ... 5.25 Ratio
Author Response: The three alerts refer to a tert-butyl group that exhibits some degree of rotational disorder. The elongated anisotropic displacement parameter for C20 is acceptable under these circumstances.
PLAT222_ALERT_3_A Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       6.04 Ratio
Author Response: as above.
PLAT242_ALERT_2_A Check Low       Ueq as Compared to Neighbors for        C19
Author Response: as above.

Alert level B PLAT029_ALERT_3_B _diffrn_measured_fraction_theta_full Low ....... 0.96
Alert level C PLAT213_ALERT_2_C Atom C20 has ADP max/min Ratio ............. 3.20 prola PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C8
Author Response: as above.
PLAT412_ALERT_2_C Short Intra XH3 .. XHn     H12    ..  H20B    ..       1.81 Ang.

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 27.09 From the CIF: _reflns_number_total 4238 Count of symmetry unique reflns 2672 Completeness (_total/calc) 158.61% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 1566 Fraction of Friedel pairs measured 0.586 Are heavy atom types Z>Si present yes PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K
3 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 3 ALERT level G = General alerts; check 2 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 2 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 (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Sheldrick, 2001); software used to prepare material for publication: SHELXTL.

bis[2-(tert-buyliminomethyl)phenolato-κ2N,O]iron(II) top
Crystal data top
[Fe(C11H14NO)2F(000) = 864
Mr = 408.31Dx = 1.272 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 5823 reflections
a = 10.080 (2) Åθ = 2.3–25.2°
b = 10.219 (2) ŵ = 0.73 mm1
c = 20.699 (4) ÅT = 293 K
V = 2132.2 (7) Å3Block, red
Z = 40.35 × 0.24 × 0.10 mm
Data collection top
Bruker SMART CCD
diffractometer
4238 independent reflections
Radiation source: fine-focus sealed tube3815 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.034
φ and ω scansθmax = 27.1°, θmin = 2.3°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1212
Tmin = 0.785, Tmax = 0.931k = 139
9491 measured reflectionsl = 2619
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.040H-atom parameters constrained
wR(F2) = 0.105 w = 1/[σ2(Fo2) + (0.0634P)2 + 0.2356P]
where P = (Fo2 + 2Fc2)/3
S = 1.10(Δ/σ)max < 0.001
4238 reflectionsΔρmax = 0.38 e Å3
250 parametersΔρmin = 0.47 e Å3
0 restraintsAbsolute structure: Flack (1983), 1676 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.001 (18)
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
Fe10.67067 (3)0.44399 (4)0.823289 (19)0.03691 (12)
O10.68309 (17)0.5935 (2)0.87917 (10)0.0450 (5)
O20.74860 (19)0.4572 (2)0.73923 (10)0.0456 (5)
N10.46703 (19)0.4357 (2)0.83172 (11)0.0367 (5)
N20.7910 (2)0.2894 (2)0.84959 (12)0.0393 (5)
C10.5895 (2)0.6654 (3)0.90482 (13)0.0345 (5)
C20.6238 (3)0.7815 (3)0.93724 (15)0.0415 (6)
H20.71250.80600.93980.050*
C30.5279 (3)0.8602 (3)0.96551 (16)0.0476 (7)
H30.55310.93660.98660.057*
C40.3949 (3)0.8261 (3)0.96268 (18)0.0510 (8)
H40.33110.87840.98240.061*
C50.3588 (2)0.7148 (3)0.93060 (16)0.0451 (7)
H50.26940.69240.92880.054*
C60.4531 (2)0.6319 (3)0.89994 (14)0.0367 (6)
C70.4014 (2)0.5231 (3)0.86428 (14)0.0376 (6)
H70.30960.51390.86450.045*
C80.3882 (3)0.3353 (3)0.79462 (15)0.0424 (7)
C90.4841 (3)0.2326 (4)0.7701 (2)0.0691 (11)
H9A0.55410.27430.74640.104*
H9B0.43790.17260.74240.104*
H9C0.52100.18580.80610.104*
C100.3227 (5)0.4023 (5)0.7375 (2)0.0754 (11)
H10A0.26160.46720.75290.113*
H10B0.27580.33860.71220.113*
H10C0.38930.44340.71130.113*
C110.2847 (5)0.2704 (5)0.8369 (2)0.0790 (14)
H11A0.32760.22640.87210.118*
H11B0.23550.20810.81180.118*
H11C0.22530.33560.85360.118*
C120.8693 (2)0.2341 (3)0.80844 (15)0.0421 (7)
H120.91830.16360.82390.050*
C130.8905 (2)0.2678 (3)0.74143 (15)0.0412 (6)
C140.9808 (3)0.1892 (4)0.70604 (17)0.0510 (8)
H141.01730.11570.72570.061*
C151.0157 (3)0.2184 (4)0.64404 (17)0.0544 (9)
H151.07490.16520.62170.065*
C160.9621 (3)0.3283 (4)0.61461 (16)0.0506 (8)
H160.98590.34860.57240.061*
C170.8745 (3)0.4075 (3)0.64692 (15)0.0456 (7)
H170.84090.48140.62640.055*
C180.8345 (3)0.3787 (3)0.71090 (14)0.0403 (6)
C190.7974 (3)0.2486 (4)0.91883 (16)0.0487 (7)
C200.8385 (13)0.1097 (7)0.9287 (3)0.182 (5)
H20A0.85580.09480.97370.272*
H20B0.91740.09240.90410.272*
H20C0.76870.05260.91450.272*
C210.6688 (5)0.2772 (8)0.9502 (2)0.121 (3)
H21A0.60010.22690.92980.181*
H21B0.64930.36870.94610.181*
H21C0.67370.25440.99520.181*
C220.8984 (5)0.3380 (8)0.9502 (2)0.120 (3)
H22A0.88210.42670.93720.180*
H22B0.98600.31260.93710.180*
H22C0.89110.33150.99640.180*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Fe10.03041 (16)0.0355 (2)0.0449 (2)0.00187 (15)0.00400 (15)0.00501 (19)
O10.0260 (8)0.0499 (12)0.0592 (12)0.0006 (8)0.0038 (8)0.0154 (10)
O20.0464 (10)0.0392 (12)0.0512 (11)0.0105 (9)0.0080 (8)0.0038 (11)
N10.0313 (9)0.0360 (12)0.0426 (12)0.0022 (8)0.0009 (8)0.0029 (12)
N20.0358 (10)0.0349 (13)0.0472 (13)0.0001 (9)0.0025 (9)0.0028 (11)
C10.0295 (11)0.0364 (14)0.0376 (13)0.0029 (10)0.0010 (10)0.0061 (12)
C20.0381 (12)0.0422 (17)0.0444 (15)0.0000 (11)0.0005 (11)0.0066 (14)
C30.0538 (16)0.0403 (17)0.0489 (17)0.0031 (13)0.0019 (13)0.0076 (15)
C40.0442 (14)0.0464 (18)0.062 (2)0.0118 (13)0.0070 (13)0.0111 (17)
C50.0302 (12)0.0472 (18)0.0579 (18)0.0073 (11)0.0044 (11)0.0063 (15)
C60.0304 (11)0.0386 (15)0.0410 (14)0.0033 (10)0.0022 (10)0.0033 (13)
C70.0252 (10)0.0426 (16)0.0449 (14)0.0003 (10)0.0023 (10)0.0013 (12)
C80.0363 (12)0.0406 (16)0.0502 (16)0.0116 (11)0.0034 (11)0.0082 (14)
C90.0524 (18)0.060 (2)0.095 (3)0.0041 (16)0.0104 (18)0.035 (2)
C100.092 (3)0.066 (2)0.068 (2)0.013 (2)0.037 (2)0.005 (2)
C110.089 (3)0.078 (3)0.070 (3)0.047 (2)0.021 (2)0.019 (2)
C120.0366 (12)0.0374 (15)0.0521 (18)0.0046 (10)0.0053 (11)0.0039 (13)
C130.0306 (11)0.0443 (16)0.0487 (16)0.0035 (11)0.0018 (11)0.0070 (14)
C140.0343 (13)0.055 (2)0.064 (2)0.0110 (12)0.0020 (13)0.0101 (17)
C150.0344 (13)0.070 (2)0.059 (2)0.0100 (14)0.0042 (13)0.0236 (19)
C160.0403 (13)0.062 (2)0.0498 (17)0.0049 (13)0.0073 (12)0.0129 (17)
C170.0424 (13)0.0483 (18)0.0461 (16)0.0011 (11)0.0049 (11)0.0059 (14)
C180.0313 (11)0.0421 (15)0.0474 (15)0.0023 (12)0.0056 (11)0.0077 (13)
C190.0517 (16)0.0459 (18)0.0487 (17)0.0033 (12)0.0017 (13)0.0065 (15)
C200.417 (15)0.059 (3)0.068 (3)0.049 (6)0.042 (6)0.020 (3)
C210.066 (2)0.233 (8)0.063 (2)0.034 (4)0.020 (2)0.056 (4)
C220.100 (3)0.202 (8)0.057 (3)0.067 (4)0.025 (2)0.023 (4)
Geometric parameters (Å, º) top
Fe1—O21.914 (2)C10—H10B0.960
Fe1—O11.920 (2)C10—H10C0.960
Fe1—N12.062 (2)C11—H11A0.960
Fe1—N22.064 (2)C11—H11B0.960
O1—C11.308 (3)C11—H11C0.960
O2—C181.318 (3)C12—C131.445 (4)
N1—C71.300 (4)C12—H120.930
N1—C81.508 (4)C13—C181.415 (4)
N2—C121.292 (4)C13—C141.418 (4)
N2—C191.494 (4)C14—C151.364 (5)
C1—C21.406 (4)C14—H140.930
C1—C61.420 (4)C15—C161.387 (6)
C2—C31.387 (4)C15—H150.930
C2—H20.930C16—C171.372 (4)
C3—C41.386 (4)C16—H160.930
C3—H30.930C17—C181.415 (4)
C4—C51.367 (5)C17—H170.930
C4—H40.930C19—C211.479 (5)
C5—C61.422 (4)C19—C201.492 (7)
C5—H50.930C19—C221.515 (6)
C6—C71.433 (4)C20—H20A0.960
C7—H70.930C20—H20B0.960
C8—C91.514 (5)C20—H20C0.960
C8—C111.515 (5)C21—H21A0.960
C8—C101.517 (5)C21—H21B0.960
C9—H9A0.960C21—H21C0.960
C9—H9B0.960C22—H22A0.960
C9—H9C0.960C22—H22B0.960
C10—H10A0.960C22—H22C0.960
O2—Fe1—O1117.70 (10)H10B—C10—H10C109.5
O2—Fe1—N1119.24 (9)C8—C11—H11A109.5
O1—Fe1—N192.67 (8)C8—C11—H11B109.5
O2—Fe1—N293.01 (9)H11A—C11—H11B109.5
O1—Fe1—N2114.31 (9)C8—C11—H11C109.5
N1—Fe1—N2122.07 (10)H11A—C11—H11C109.5
C1—O1—Fe1130.12 (17)H11B—C11—H11C109.5
C18—O2—Fe1129.2 (2)N2—C12—C13128.2 (3)
C7—N1—C8117.6 (2)N2—C12—H12115.9
C7—N1—Fe1121.49 (18)C13—C12—H12115.9
C8—N1—Fe1120.63 (17)C18—C13—C14118.6 (3)
C12—N2—C19118.9 (3)C18—C13—C12124.1 (3)
C12—N2—Fe1121.3 (2)C14—C13—C12117.1 (3)
C19—N2—Fe1119.48 (19)C15—C14—C13121.9 (3)
O1—C1—C2119.4 (2)C15—C14—H14119.1
O1—C1—C6122.2 (2)C13—C14—H14119.1
C2—C1—C6118.4 (2)C14—C15—C16119.3 (3)
C3—C2—C1121.3 (3)C14—C15—H15120.3
C3—C2—H2119.4C16—C15—H15120.3
C1—C2—H2119.4C17—C16—C15121.0 (3)
C4—C3—C2120.7 (3)C17—C16—H16119.5
C4—C3—H3119.6C15—C16—H16119.5
C2—C3—H3119.6C16—C17—C18121.1 (3)
C5—C4—C3119.1 (3)C16—C17—H17119.4
C5—C4—H4120.4C18—C17—H17119.4
C3—C4—H4120.4O2—C18—C13123.4 (3)
C4—C5—C6122.3 (3)O2—C18—C17118.5 (3)
C4—C5—H5118.9C13—C18—C17118.1 (3)
C6—C5—H5118.9C21—C19—C20111.8 (6)
C1—C6—C5118.2 (3)C21—C19—N2109.2 (3)
C1—C6—C7125.2 (2)C20—C19—N2114.1 (3)
C5—C6—C7116.6 (2)C21—C19—C22106.3 (5)
N1—C7—C6128.0 (2)C20—C19—C22109.2 (6)
N1—C7—H7116.0N2—C19—C22105.8 (3)
C6—C7—H7116.0C19—C20—H20A109.5
N1—C8—C9107.8 (2)C19—C20—H20B109.5
N1—C8—C11111.5 (3)H20A—C20—H20B109.5
C9—C8—C11109.2 (4)C19—C20—H20C109.5
N1—C8—C10108.6 (3)H20A—C20—H20C109.5
C9—C8—C10109.3 (3)H20B—C20—H20C109.5
C11—C8—C10110.4 (3)C19—C21—H21A109.5
C8—C9—H9A109.5C19—C21—H21B109.5
C8—C9—H9B109.5H21A—C21—H21B109.5
H9A—C9—H9B109.5C19—C21—H21C109.5
C8—C9—H9C109.5H21A—C21—H21C109.5
H9A—C9—H9C109.5H21B—C21—H21C109.5
H9B—C9—H9C109.5C19—C22—H22A109.5
C8—C10—H10A109.5C19—C22—H22B109.5
C8—C10—H10B109.5H22A—C22—H22B109.5
H10A—C10—H10B109.5C19—C22—H22C109.5
C8—C10—H10C109.5H22A—C22—H22C109.5
H10A—C10—H10C109.5H22B—C22—H22C109.5
O2—Fe1—O1—C1118.8 (2)Fe1—N1—C7—C62.1 (4)
N1—Fe1—O1—C16.5 (3)C1—C6—C7—N11.4 (5)
N2—Fe1—O1—C1133.7 (2)C5—C6—C7—N1179.0 (3)
O1—Fe1—O2—C18127.3 (2)C7—N1—C8—C9170.9 (3)
N1—Fe1—O2—C18122.0 (2)Fe1—N1—C8—C915.1 (4)
N2—Fe1—O2—C187.7 (2)C7—N1—C8—C1151.0 (4)
O2—Fe1—N1—C7120.4 (2)Fe1—N1—C8—C11135.0 (3)
O1—Fe1—N1—C73.6 (2)C7—N1—C8—C1070.8 (4)
N2—Fe1—N1—C7124.6 (2)Fe1—N1—C8—C10103.2 (3)
O2—Fe1—N1—C853.4 (2)C19—N2—C12—C13172.5 (3)
O1—Fe1—N1—C8177.4 (2)Fe1—N2—C12—C131.7 (4)
N2—Fe1—N1—C861.6 (2)N2—C12—C13—C186.0 (5)
O2—Fe1—N2—C126.8 (2)N2—C12—C13—C14178.8 (3)
O1—Fe1—N2—C12129.1 (2)C18—C13—C14—C150.7 (5)
N1—Fe1—N2—C12120.8 (2)C12—C13—C14—C15174.9 (3)
O2—Fe1—N2—C19167.3 (2)C13—C14—C15—C160.3 (5)
O1—Fe1—N2—C1945.0 (2)C14—C15—C16—C170.1 (5)
N1—Fe1—N2—C1965.1 (2)C15—C16—C17—C181.0 (5)
Fe1—O1—C1—C2171.3 (2)Fe1—O2—C18—C133.0 (4)
Fe1—O1—C1—C67.3 (4)Fe1—O2—C18—C17178.0 (2)
O1—C1—C2—C3179.5 (3)C14—C13—C18—O2179.2 (3)
C6—C1—C2—C31.8 (5)C12—C13—C18—O25.6 (4)
C1—C2—C3—C40.1 (5)C14—C13—C18—C171.7 (4)
C2—C3—C4—C51.1 (5)C12—C13—C18—C17173.5 (3)
C3—C4—C5—C60.1 (5)C16—C17—C18—O2179.0 (3)
O1—C1—C6—C5178.7 (3)C16—C17—C18—C131.9 (4)
C2—C1—C6—C52.7 (4)C12—N2—C19—C21155.6 (4)
O1—C1—C6—C73.8 (5)Fe1—N2—C19—C2130.1 (5)
C2—C1—C6—C7174.8 (3)C12—N2—C19—C2029.8 (7)
C4—C5—C6—C11.8 (5)Fe1—N2—C19—C20155.9 (6)
C4—C5—C6—C7175.9 (3)C12—N2—C19—C2290.3 (4)
C8—N1—C7—C6176.1 (3)Fe1—N2—C19—C2284.0 (4)
 

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