A dinuclear Schiff base iron(III) complex with the ligand N,N′-bis(2-oxido­phenyl­methyl­eneimino)­propane-1,2-di­amine

The centrosymmetric title compound, bis­[μ-N,N′-bis(μ-2-oxido­phenyl­methyl­eneimino)­propane-1,2-diaminato(3−)]­iron(III), [Fe₂(C₁₇H₁₆ClN₂O₂)₂], is a dinuclear iron(III) complex. Each Fe^III atom is six-coordinated by two N atoms and three O atoms from two Schiff base ligands, and one Cl atom, giving an approximately octahedral coordination environment.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.012 Å
• R factor = 0.086
• wR factor = 0.224
• Data-to-parameter ratio = 13.6

checkCIF/PLATON results

No syntax errors found



Alert level B
RINTA01_ALERT_3_B  The value of Rint is greater than 0.15
            Rint given   0.176
PLAT020_ALERT_3_B The value of Rint is greater than 0.10 .........       0.18

Alert level C
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.15
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.45 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.69 Ratio
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C11    -   C12     ..       5.04 su
PLAT241_ALERT_2_C Check High   U(eq) as Compared to Neighbors ....        C10
PLAT242_ALERT_2_C Check Low    U(eq) as Compared to Neighbors ....         C8
PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...         12

   0 ALERT level A = In general: serious problem
   2 ALERT level B = Potentially serious problem
   7 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 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
   4 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion

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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: SHELXTL.

bis[µ-N,N'-bis(µ-2-oxidophenylmethyleneamino)propane-1,2- diaminato(3-)]iron(III)

Crystal data

[Fe2(C17H16ClN2O2)2]	F(000) = 764
Mr = 743.24	Dx = 1.510 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2307 reflections
a = 10.937 (8) Å	θ = 2.2–22.3°
b = 20.406 (14) Å	µ = 1.10 mm^−1
c = 7.484 (5) Å	T = 298 K
β = 101.864 (11)°	Block, brown
V = 1635 (2) Å^3	0.28 × 0.22 × 0.14 mm
Z = 2

Data collection

Siemens SMART CCD area-detector diffractometer	2838 independent reflections
Radiation source: fine-focus sealed tube	1515 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.176
ω scans	θmax = 25.0°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −13→12
Tmin = 0.749, Tmax = 0.862	k = −24→23
8018 measured reflections	l = −8→6

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)] = 0.086	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.224	H-atom parameters constrained
S = 0.94	w = 1/[σ^2(Fo^2) + (0.1021P)^2] where P = (Fo^2 + 2Fc^2)/3
2838 reflections	(Δ/σ)max < 0.001
209 parameters	Δρmax = 1.30 e Å^−3
0 restraints	Δρmin = −0.61 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	−0.00368 (9)	0.42045 (4)	0.46127 (13)	0.0469 (4)
Cl1	0.0462 (2)	0.35261 (10)	0.2404 (3)	0.0711 (7)
O1	0.0379 (4)	0.50276 (19)	0.3477 (6)	0.0428 (11)
O2	−0.1781 (4)	0.4085 (2)	0.3954 (6)	0.0489 (12)
N1	0.1828 (6)	0.4239 (3)	0.6087 (8)	0.0563 (16)
N2	−0.0006 (7)	0.3474 (3)	0.6575 (7)	0.0563 (17)
C1	0.2568 (7)	0.4812 (3)	0.3684 (10)	0.0537 (19)
C2	0.1423 (6)	0.5084 (3)	0.2802 (9)	0.0446 (17)
C3	0.1377 (7)	0.5418 (3)	0.1170 (9)	0.0516 (18)
H3	0.0613	0.5571	0.0523	0.062*
C4	0.2414 (8)	0.5524 (4)	0.0505 (11)	0.067 (2)
H4	0.2365	0.5768	−0.0557	0.080*
C5	0.3568 (8)	0.5269 (5)	0.1404 (12)	0.075 (2)
H5	0.4279	0.5331	0.0924	0.090*
C6	0.3637 (7)	0.4930 (4)	0.2989 (11)	0.066 (2)
H6	0.4406	0.4775	0.3616	0.079*
C7	0.2709 (7)	0.4467 (4)	0.5459 (10)	0.059 (2)
H7	0.3512	0.4416	0.6153	0.071*
C8	0.2010 (8)	0.3919 (5)	0.7885 (11)	0.075 (3)
H8	0.1704	0.4206	0.8746	0.090*
C9	0.3303 (11)	0.3671 (7)	0.8746 (18)	0.152 (5)
H9A	0.3494	0.3293	0.8092	0.229*
H9B	0.3327	0.3556	0.9996	0.229*
H9C	0.3906	0.4009	0.8696	0.229*
C10	0.1252 (9)	0.3307 (4)	0.7621 (12)	0.085 (3)
H10A	0.1641	0.2986	0.6959	0.101*
H10B	0.1195	0.3122	0.8795	0.101*
C11	−0.0965 (10)	0.3154 (4)	0.6835 (10)	0.073 (3)
H11	−0.0815	0.2833	0.7736	0.087*
C12	−0.2224 (8)	0.3230 (4)	0.5917 (10)	0.062 (2)
C13	−0.2575 (7)	0.3688 (3)	0.4483 (9)	0.0504 (18)
C14	−0.3826 (7)	0.3720 (4)	0.3614 (11)	0.061 (2)
H14	−0.4084	0.4013	0.2659	0.073*
C15	−0.4683 (9)	0.3313 (4)	0.4179 (13)	0.082 (3)
H15	−0.5517	0.3344	0.3590	0.098*
C16	−0.4374 (11)	0.2875 (5)	0.5535 (14)	0.093 (3)
H16	−0.4974	0.2604	0.5869	0.111*
C17	−0.3146 (11)	0.2839 (4)	0.6412 (13)	0.086 (3)
H17	−0.2919	0.2544	0.7370	0.103*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Fe1	0.0553 (7)	0.0381 (6)	0.0474 (7)	0.0048 (5)	0.0107 (5)	0.0065 (4)
Cl1	0.0952 (17)	0.0569 (12)	0.0636 (13)	0.0098 (11)	0.0222 (11)	−0.0064 (9)
O1	0.045 (3)	0.035 (2)	0.049 (3)	0.006 (2)	0.012 (2)	0.0064 (19)
O2	0.043 (3)	0.046 (3)	0.056 (3)	−0.004 (2)	0.006 (2)	0.005 (2)
N1	0.057 (4)	0.061 (4)	0.049 (4)	0.011 (3)	0.007 (3)	0.006 (3)
N2	0.089 (5)	0.035 (3)	0.044 (4)	0.011 (3)	0.012 (3)	0.016 (3)
C1	0.046 (5)	0.051 (4)	0.066 (5)	0.005 (4)	0.015 (4)	−0.007 (4)
C2	0.043 (4)	0.040 (4)	0.052 (4)	0.001 (3)	0.014 (3)	−0.007 (3)
C3	0.057 (5)	0.052 (5)	0.045 (4)	−0.005 (4)	0.008 (3)	−0.004 (3)
C4	0.072 (6)	0.075 (5)	0.055 (5)	−0.015 (5)	0.019 (4)	0.002 (4)
C5	0.054 (5)	0.111 (7)	0.065 (6)	−0.016 (5)	0.026 (4)	−0.014 (5)
C6	0.051 (5)	0.072 (6)	0.072 (6)	−0.006 (4)	0.008 (4)	−0.008 (4)
C7	0.051 (5)	0.067 (5)	0.055 (5)	0.016 (4)	0.002 (4)	−0.001 (4)
C8	0.066 (6)	0.093 (7)	0.059 (5)	0.033 (5)	−0.001 (4)	0.017 (5)
C9	0.102 (10)	0.180 (14)	0.165 (12)	−0.005 (9)	0.005 (8)	0.053 (11)
C10	0.114 (8)	0.060 (6)	0.078 (6)	0.009 (6)	0.017 (5)	0.031 (5)
C11	0.123 (8)	0.041 (4)	0.058 (5)	−0.004 (5)	0.026 (5)	0.012 (4)
C12	0.085 (7)	0.046 (4)	0.053 (5)	−0.004 (4)	0.008 (4)	0.002 (4)
C13	0.059 (5)	0.046 (4)	0.050 (4)	−0.006 (4)	0.018 (4)	−0.010 (3)
C14	0.061 (5)	0.059 (5)	0.070 (5)	−0.011 (4)	0.028 (4)	−0.011 (4)
C15	0.074 (6)	0.067 (6)	0.110 (8)	−0.022 (5)	0.032 (5)	−0.018 (5)
C16	0.105 (9)	0.089 (7)	0.089 (7)	−0.043 (7)	0.034 (6)	0.010 (6)
C17	0.122 (9)	0.061 (6)	0.081 (7)	−0.021 (6)	0.039 (6)	0.019 (5)

Geometric parameters (Å, º)

Fe1—O2	1.886 (5)	C6—H6	0.93
Fe1—O1	1.977 (4)	C7—H7	0.93
Fe1—N2	2.089 (6)	C8—C10	1.489 (12)
Fe1—N1	2.111 (6)	C8—C9	1.515 (13)
Fe1—O1^i	2.205 (4)	C8—H8	0.98
Fe1—Cl1	2.306 (2)	C9—H9A	0.96
O1—C2	1.345 (8)	C9—H9B	0.96
O1—Fe1^i	2.205 (4)	C9—H9C	0.96
O2—C13	1.307 (8)	C10—H10A	0.97
N1—C7	1.245 (9)	C10—H10B	0.97
N1—C8	1.473 (9)	C11—C12	1.415 (11)
N2—C11	1.284 (10)	C11—H11	0.93
N2—C10	1.477 (10)	C12—C17	1.395 (11)
C1—C6	1.394 (10)	C12—C13	1.415 (10)
C1—C2	1.404 (10)	C13—C14	1.391 (10)
C1—C7	1.484 (10)	C14—C15	1.382 (11)
C2—C3	1.390 (9)	C14—H14	0.93
C3—C4	1.346 (10)	C15—C16	1.342 (13)
C3—H3	0.93	C15—H15	0.93
C4—C5	1.403 (12)	C16—C17	1.371 (12)
C4—H4	0.93	C16—H16	0.93
C5—C6	1.362 (11)	C17—H17	0.93
C5—H5	0.93
O2—Fe1—O1	107.90 (19)	N1—C7—C1	124.7 (7)
O2—Fe1—N2	87.7 (2)	N1—C7—H7	117.6
O1—Fe1—N2	159.5 (2)	C1—C7—H7	117.6
O2—Fe1—N1	163.3 (2)	N1—C8—C10	106.5 (7)
O1—Fe1—N1	85.0 (2)	N1—C8—C9	118.4 (8)
N2—Fe1—N1	77.4 (3)	C10—C8—C9	102.9 (8)
O2—Fe1—O1^i	87.92 (18)	N1—C8—H8	109.5
O1—Fe1—O1^i	76.10 (19)	C10—C8—H8	109.5
N2—Fe1—O1^i	91.81 (19)	C9—C8—H8	109.5
N1—Fe1—O1^i	85.0 (2)	C8—C9—H9A	109.5
O2—Fe1—Cl1	96.35 (15)	C8—C9—H9B	109.5
O1—Fe1—Cl1	95.31 (14)	H9A—C9—H9B	109.5
N2—Fe1—Cl1	95.95 (17)	C8—C9—H9C	109.5
N1—Fe1—Cl1	92.83 (18)	H9A—C9—H9C	109.5
O1^i—Fe1—Cl1	171.27 (13)	H9B—C9—H9C	109.5
C2—O1—Fe1	121.5 (4)	N2—C10—C8	108.0 (6)
C2—O1—Fe1^i	116.9 (4)	N2—C10—H10A	110.1
Fe1—O1—Fe1^i	103.90 (18)	C8—C10—H10A	110.1
C13—O2—Fe1	134.4 (5)	N2—C10—H10B	110.1
C7—N1—C8	122.7 (7)	C8—C10—H10B	110.1
C7—N1—Fe1	123.7 (5)	H10A—C10—H10B	108.4
C8—N1—Fe1	113.4 (5)	N2—C11—C12	127.9 (7)
C11—N2—C10	120.3 (7)	N2—C11—H11	116.0
C11—N2—Fe1	125.0 (6)	C12—C11—H11	116.0
C10—N2—Fe1	114.6 (5)	C17—C12—C13	118.7 (8)
C6—C1—C2	119.4 (7)	C17—C12—C11	119.5 (8)
C6—C1—C7	118.4 (7)	C13—C12—C11	121.8 (7)
C2—C1—C7	121.8 (6)	O2—C13—C14	118.7 (7)
O1—C2—C3	119.5 (6)	O2—C13—C12	123.0 (7)
O1—C2—C1	122.2 (6)	C14—C13—C12	118.3 (7)
C3—C2—C1	118.3 (6)	C15—C14—C13	119.5 (8)
C4—C3—C2	121.5 (7)	C15—C14—H14	120.3
C4—C3—H3	119.2	C13—C14—H14	120.3
C2—C3—H3	119.2	C16—C15—C14	123.4 (9)
C3—C4—C5	120.4 (8)	C16—C15—H15	118.3
C3—C4—H4	119.8	C14—C15—H15	118.3
C5—C4—H4	119.8	C15—C16—C17	117.8 (9)
C6—C5—C4	119.3 (7)	C15—C16—H16	121.1
C6—C5—H5	120.3	C17—C16—H16	121.1
C4—C5—H5	120.3	C16—C17—C12	122.2 (8)
C5—C6—C1	120.8 (7)	C16—C17—H17	118.9
C5—C6—H6	119.6	C12—C17—H17	118.9
C1—C6—H6	119.6

Symmetry code: (i) −x, −y+1, −z+1.