Bis(N-tert-butylsalicylaldiminato)iron(II)

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 Fe^II atom exhibits a distorted tetra­hedral coordination geometry.

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

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Computing details

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)

Crystal data

[Fe(C11H14NO)2	F(000) = 864
Mr = 408.31	Dx = 1.272 Mg m^−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 5823 reflections
a = 10.080 (2) Å	θ = 2.3–25.2°
b = 10.219 (2) Å	µ = 0.73 mm^−1
c = 20.699 (4) Å	T = 293 K
V = 2132.2 (7) Å^3	Block, red
Z = 4	0.35 × 0.24 × 0.10 mm

Data collection

Bruker SMART CCD diffractometer	4238 independent reflections
Radiation source: fine-focus sealed tube	3815 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.034
φ and ω scans	θmax = 27.1°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→12
Tmin = 0.785, Tmax = 0.931	k = −13→9
9491 measured reflections	l = −26→19

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.040	H-atom parameters constrained
wR(F^2) = 0.105	w = 1/[σ^2(Fo^2) + (0.0634P)^2 + 0.2356P] where P = (Fo^2 + 2Fc^2)/3
S = 1.10	(Δ/σ)max < 0.001
4238 reflections	Δρmax = 0.38 e Å^−3
250 parameters	Δρmin = −0.47 e Å^−3
0 restraints	Absolute structure: Flack (1983), 1676 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.001 (18)

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	0.67067 (3)	0.44399 (4)	0.823289 (19)	0.03691 (12)
O1	0.68309 (17)	0.5935 (2)	0.87917 (10)	0.0450 (5)
O2	0.74860 (19)	0.4572 (2)	0.73923 (10)	0.0456 (5)
N1	0.46703 (19)	0.4357 (2)	0.83172 (11)	0.0367 (5)
N2	0.7910 (2)	0.2894 (2)	0.84959 (12)	0.0393 (5)
C1	0.5895 (2)	0.6654 (3)	0.90482 (13)	0.0345 (5)
C2	0.6238 (3)	0.7815 (3)	0.93724 (15)	0.0415 (6)
H2	0.7125	0.8060	0.9398	0.050*
C3	0.5279 (3)	0.8602 (3)	0.96551 (16)	0.0476 (7)
H3	0.5531	0.9366	0.9866	0.057*
C4	0.3949 (3)	0.8261 (3)	0.96268 (18)	0.0510 (8)
H4	0.3311	0.8784	0.9824	0.061*
C5	0.3588 (2)	0.7148 (3)	0.93060 (16)	0.0451 (7)
H5	0.2694	0.6924	0.9288	0.054*
C6	0.4531 (2)	0.6319 (3)	0.89994 (14)	0.0367 (6)
C7	0.4014 (2)	0.5231 (3)	0.86428 (14)	0.0376 (6)
H7	0.3096	0.5139	0.8645	0.045*
C8	0.3882 (3)	0.3353 (3)	0.79462 (15)	0.0424 (7)
C9	0.4841 (3)	0.2326 (4)	0.7701 (2)	0.0691 (11)
H9A	0.5541	0.2743	0.7464	0.104*
H9B	0.4379	0.1726	0.7424	0.104*
H9C	0.5210	0.1858	0.8061	0.104*
C10	0.3227 (5)	0.4023 (5)	0.7375 (2)	0.0754 (11)
H10A	0.2616	0.4672	0.7529	0.113*
H10B	0.2758	0.3386	0.7122	0.113*
H10C	0.3893	0.4434	0.7113	0.113*
C11	0.2847 (5)	0.2704 (5)	0.8369 (2)	0.0790 (14)
H11A	0.3276	0.2264	0.8721	0.118*
H11B	0.2355	0.2081	0.8118	0.118*
H11C	0.2253	0.3356	0.8536	0.118*
C12	0.8693 (2)	0.2341 (3)	0.80844 (15)	0.0421 (7)
H12	0.9183	0.1636	0.8239	0.050*
C13	0.8905 (2)	0.2678 (3)	0.74143 (15)	0.0412 (6)
C14	0.9808 (3)	0.1892 (4)	0.70604 (17)	0.0510 (8)
H14	1.0173	0.1157	0.7257	0.061*
C15	1.0157 (3)	0.2184 (4)	0.64404 (17)	0.0544 (9)
H15	1.0749	0.1652	0.6217	0.065*
C16	0.9621 (3)	0.3283 (4)	0.61461 (16)	0.0506 (8)
H16	0.9859	0.3486	0.5724	0.061*
C17	0.8745 (3)	0.4075 (3)	0.64692 (15)	0.0456 (7)
H17	0.8409	0.4814	0.6264	0.055*
C18	0.8345 (3)	0.3787 (3)	0.71090 (14)	0.0403 (6)
C19	0.7974 (3)	0.2486 (4)	0.91883 (16)	0.0487 (7)
C20	0.8385 (13)	0.1097 (7)	0.9287 (3)	0.182 (5)
H20A	0.8558	0.0948	0.9737	0.272*
H20B	0.9174	0.0924	0.9041	0.272*
H20C	0.7687	0.0526	0.9145	0.272*
C21	0.6688 (5)	0.2772 (8)	0.9502 (2)	0.121 (3)
H21A	0.6001	0.2269	0.9298	0.181*
H21B	0.6493	0.3687	0.9461	0.181*
H21C	0.6737	0.2544	0.9952	0.181*
C22	0.8984 (5)	0.3380 (8)	0.9502 (2)	0.120 (3)
H22A	0.8821	0.4267	0.9372	0.180*
H22B	0.9860	0.3126	0.9371	0.180*
H22C	0.8911	0.3315	0.9964	0.180*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Fe1	0.03041 (16)	0.0355 (2)	0.0449 (2)	0.00187 (15)	0.00400 (15)	−0.00501 (19)
O1	0.0260 (8)	0.0499 (12)	0.0592 (12)	0.0006 (8)	0.0038 (8)	−0.0154 (10)
O2	0.0464 (10)	0.0392 (12)	0.0512 (11)	0.0105 (9)	0.0080 (8)	−0.0038 (11)
N1	0.0313 (9)	0.0360 (12)	0.0426 (12)	−0.0022 (8)	−0.0009 (8)	−0.0029 (12)
N2	0.0358 (10)	0.0349 (13)	0.0472 (13)	−0.0001 (9)	−0.0025 (9)	−0.0028 (11)
C1	0.0295 (11)	0.0364 (14)	0.0376 (13)	0.0029 (10)	−0.0010 (10)	−0.0061 (12)
C2	0.0381 (12)	0.0422 (17)	0.0444 (15)	0.0000 (11)	−0.0005 (11)	−0.0066 (14)
C3	0.0538 (16)	0.0403 (17)	0.0489 (17)	0.0031 (13)	−0.0019 (13)	−0.0076 (15)
C4	0.0442 (14)	0.0464 (18)	0.062 (2)	0.0118 (13)	0.0070 (13)	−0.0111 (17)
C5	0.0302 (12)	0.0472 (18)	0.0579 (18)	0.0073 (11)	0.0044 (11)	−0.0063 (15)
C6	0.0304 (11)	0.0386 (15)	0.0410 (14)	0.0033 (10)	0.0022 (10)	−0.0033 (13)
C7	0.0252 (10)	0.0426 (16)	0.0449 (14)	0.0003 (10)	0.0023 (10)	−0.0013 (12)
C8	0.0363 (12)	0.0406 (16)	0.0502 (16)	−0.0116 (11)	−0.0034 (11)	−0.0082 (14)
C9	0.0524 (18)	0.060 (2)	0.095 (3)	−0.0041 (16)	−0.0104 (18)	−0.035 (2)
C10	0.092 (3)	0.066 (2)	0.068 (2)	−0.013 (2)	−0.037 (2)	−0.005 (2)
C11	0.089 (3)	0.078 (3)	0.070 (3)	−0.047 (2)	0.021 (2)	−0.019 (2)
C12	0.0366 (12)	0.0374 (15)	0.0521 (18)	0.0046 (10)	−0.0053 (11)	−0.0039 (13)
C13	0.0306 (11)	0.0443 (16)	0.0487 (16)	0.0035 (11)	−0.0018 (11)	−0.0070 (14)
C14	0.0343 (13)	0.055 (2)	0.064 (2)	0.0110 (12)	−0.0020 (13)	−0.0101 (17)
C15	0.0344 (13)	0.070 (2)	0.059 (2)	0.0100 (14)	0.0042 (13)	−0.0236 (19)
C16	0.0403 (13)	0.062 (2)	0.0498 (17)	−0.0049 (13)	0.0073 (12)	−0.0129 (17)
C17	0.0424 (13)	0.0483 (18)	0.0461 (16)	0.0011 (11)	0.0049 (11)	−0.0059 (14)
C18	0.0313 (11)	0.0421 (15)	0.0474 (15)	−0.0023 (12)	0.0056 (11)	−0.0077 (13)
C19	0.0517 (16)	0.0459 (18)	0.0487 (17)	0.0033 (12)	−0.0017 (13)	0.0065 (15)
C20	0.417 (15)	0.059 (3)	0.068 (3)	0.049 (6)	0.042 (6)	0.020 (3)
C21	0.066 (2)	0.233 (8)	0.063 (2)	0.034 (4)	0.020 (2)	0.056 (4)
C22	0.100 (3)	0.202 (8)	0.057 (3)	−0.067 (4)	−0.025 (2)	0.023 (4)

Geometric parameters (Å, º)

Fe1—O2	1.914 (2)	C10—H10B	0.960
Fe1—O1	1.920 (2)	C10—H10C	0.960
Fe1—N1	2.062 (2)	C11—H11A	0.960
Fe1—N2	2.064 (2)	C11—H11B	0.960
O1—C1	1.308 (3)	C11—H11C	0.960
O2—C18	1.318 (3)	C12—C13	1.445 (4)
N1—C7	1.300 (4)	C12—H12	0.930
N1—C8	1.508 (4)	C13—C18	1.415 (4)
N2—C12	1.292 (4)	C13—C14	1.418 (4)
N2—C19	1.494 (4)	C14—C15	1.364 (5)
C1—C2	1.406 (4)	C14—H14	0.930
C1—C6	1.420 (4)	C15—C16	1.387 (6)
C2—C3	1.387 (4)	C15—H15	0.930
C2—H2	0.930	C16—C17	1.372 (4)
C3—C4	1.386 (4)	C16—H16	0.930
C3—H3	0.930	C17—C18	1.415 (4)
C4—C5	1.367 (5)	C17—H17	0.930
C4—H4	0.930	C19—C21	1.479 (5)
C5—C6	1.422 (4)	C19—C20	1.492 (7)
C5—H5	0.930	C19—C22	1.515 (6)
C6—C7	1.433 (4)	C20—H20A	0.960
C7—H7	0.930	C20—H20B	0.960
C8—C9	1.514 (5)	C20—H20C	0.960
C8—C11	1.515 (5)	C21—H21A	0.960
C8—C10	1.517 (5)	C21—H21B	0.960
C9—H9A	0.960	C21—H21C	0.960
C9—H9B	0.960	C22—H22A	0.960
C9—H9C	0.960	C22—H22B	0.960
C10—H10A	0.960	C22—H22C	0.960
O2—Fe1—O1	117.70 (10)	H10B—C10—H10C	109.5
O2—Fe1—N1	119.24 (9)	C8—C11—H11A	109.5
O1—Fe1—N1	92.67 (8)	C8—C11—H11B	109.5
O2—Fe1—N2	93.01 (9)	H11A—C11—H11B	109.5
O1—Fe1—N2	114.31 (9)	C8—C11—H11C	109.5
N1—Fe1—N2	122.07 (10)	H11A—C11—H11C	109.5
C1—O1—Fe1	130.12 (17)	H11B—C11—H11C	109.5
C18—O2—Fe1	129.2 (2)	N2—C12—C13	128.2 (3)
C7—N1—C8	117.6 (2)	N2—C12—H12	115.9
C7—N1—Fe1	121.49 (18)	C13—C12—H12	115.9
C8—N1—Fe1	120.63 (17)	C18—C13—C14	118.6 (3)
C12—N2—C19	118.9 (3)	C18—C13—C12	124.1 (3)
C12—N2—Fe1	121.3 (2)	C14—C13—C12	117.1 (3)
C19—N2—Fe1	119.48 (19)	C15—C14—C13	121.9 (3)
O1—C1—C2	119.4 (2)	C15—C14—H14	119.1
O1—C1—C6	122.2 (2)	C13—C14—H14	119.1
C2—C1—C6	118.4 (2)	C14—C15—C16	119.3 (3)
C3—C2—C1	121.3 (3)	C14—C15—H15	120.3
C3—C2—H2	119.4	C16—C15—H15	120.3
C1—C2—H2	119.4	C17—C16—C15	121.0 (3)
C4—C3—C2	120.7 (3)	C17—C16—H16	119.5
C4—C3—H3	119.6	C15—C16—H16	119.5
C2—C3—H3	119.6	C16—C17—C18	121.1 (3)
C5—C4—C3	119.1 (3)	C16—C17—H17	119.4
C5—C4—H4	120.4	C18—C17—H17	119.4
C3—C4—H4	120.4	O2—C18—C13	123.4 (3)
C4—C5—C6	122.3 (3)	O2—C18—C17	118.5 (3)
C4—C5—H5	118.9	C13—C18—C17	118.1 (3)
C6—C5—H5	118.9	C21—C19—C20	111.8 (6)
C1—C6—C5	118.2 (3)	C21—C19—N2	109.2 (3)
C1—C6—C7	125.2 (2)	C20—C19—N2	114.1 (3)
C5—C6—C7	116.6 (2)	C21—C19—C22	106.3 (5)
N1—C7—C6	128.0 (2)	C20—C19—C22	109.2 (6)
N1—C7—H7	116.0	N2—C19—C22	105.8 (3)
C6—C7—H7	116.0	C19—C20—H20A	109.5
N1—C8—C9	107.8 (2)	C19—C20—H20B	109.5
N1—C8—C11	111.5 (3)	H20A—C20—H20B	109.5
C9—C8—C11	109.2 (4)	C19—C20—H20C	109.5
N1—C8—C10	108.6 (3)	H20A—C20—H20C	109.5
C9—C8—C10	109.3 (3)	H20B—C20—H20C	109.5
C11—C8—C10	110.4 (3)	C19—C21—H21A	109.5
C8—C9—H9A	109.5	C19—C21—H21B	109.5
C8—C9—H9B	109.5	H21A—C21—H21B	109.5
H9A—C9—H9B	109.5	C19—C21—H21C	109.5
C8—C9—H9C	109.5	H21A—C21—H21C	109.5
H9A—C9—H9C	109.5	H21B—C21—H21C	109.5
H9B—C9—H9C	109.5	C19—C22—H22A	109.5
C8—C10—H10A	109.5	C19—C22—H22B	109.5
C8—C10—H10B	109.5	H22A—C22—H22B	109.5
H10A—C10—H10B	109.5	C19—C22—H22C	109.5
C8—C10—H10C	109.5	H22A—C22—H22C	109.5
H10A—C10—H10C	109.5	H22B—C22—H22C	109.5
O2—Fe1—O1—C1	118.8 (2)	Fe1—N1—C7—C6	−2.1 (4)
N1—Fe1—O1—C1	−6.5 (3)	C1—C6—C7—N1	1.4 (5)
N2—Fe1—O1—C1	−133.7 (2)	C5—C6—C7—N1	179.0 (3)
O1—Fe1—O2—C18	127.3 (2)	C7—N1—C8—C9	−170.9 (3)
N1—Fe1—O2—C18	−122.0 (2)	Fe1—N1—C8—C9	15.1 (4)
N2—Fe1—O2—C18	7.7 (2)	C7—N1—C8—C11	−51.0 (4)
O2—Fe1—N1—C7	−120.4 (2)	Fe1—N1—C8—C11	135.0 (3)
O1—Fe1—N1—C7	3.6 (2)	C7—N1—C8—C10	70.8 (4)
N2—Fe1—N1—C7	124.6 (2)	Fe1—N1—C8—C10	−103.2 (3)
O2—Fe1—N1—C8	53.4 (2)	C19—N2—C12—C13	−172.5 (3)
O1—Fe1—N1—C8	177.4 (2)	Fe1—N2—C12—C13	1.7 (4)
N2—Fe1—N1—C8	−61.6 (2)	N2—C12—C13—C18	6.0 (5)
O2—Fe1—N2—C12	−6.8 (2)	N2—C12—C13—C14	−178.8 (3)
O1—Fe1—N2—C12	−129.1 (2)	C18—C13—C14—C15	0.7 (5)
N1—Fe1—N2—C12	120.8 (2)	C12—C13—C14—C15	−174.9 (3)
O2—Fe1—N2—C19	167.3 (2)	C13—C14—C15—C16	0.3 (5)
O1—Fe1—N2—C19	45.0 (2)	C14—C15—C16—C17	−0.1 (5)
N1—Fe1—N2—C19	−65.1 (2)	C15—C16—C17—C18	−1.0 (5)
Fe1—O1—C1—C2	−171.3 (2)	Fe1—O2—C18—C13	−3.0 (4)
Fe1—O1—C1—C6	7.3 (4)	Fe1—O2—C18—C17	178.0 (2)
O1—C1—C2—C3	−179.5 (3)	C14—C13—C18—O2	179.2 (3)
C6—C1—C2—C3	1.8 (5)	C12—C13—C18—O2	−5.6 (4)
C1—C2—C3—C4	0.1 (5)	C14—C13—C18—C17	−1.7 (4)
C2—C3—C4—C5	−1.1 (5)	C12—C13—C18—C17	173.5 (3)
C3—C4—C5—C6	0.1 (5)	C16—C17—C18—O2	−179.0 (3)
O1—C1—C6—C5	178.7 (3)	C16—C17—C18—C13	1.9 (4)
C2—C1—C6—C5	−2.7 (4)	C12—N2—C19—C21	−155.6 (4)
O1—C1—C6—C7	−3.8 (5)	Fe1—N2—C19—C21	30.1 (5)
C2—C1—C6—C7	174.8 (3)	C12—N2—C19—C20	−29.8 (7)
C4—C5—C6—C1	1.8 (5)	Fe1—N2—C19—C20	155.9 (6)
C4—C5—C6—C7	−175.9 (3)	C12—N2—C19—C22	90.3 (4)
C8—N1—C7—C6	−176.1 (3)	Fe1—N2—C19—C22	−84.0 (4)