{2,2′-[o-Phenyl­enebis(nitrilo­methyl­idyne)]diphenolato}manganese(II)

Liu, Y.-Q.; Zeng, X.-R.; Luo, Q.-Y.; Xu, Y.-P.

doi:10.1107/S1600536807052993

Retracted: {2,2'-[o-Phenylenebis(nitrilomethylidyne)]diphenolato}manganese(II)

Y.-Q. Liu, X.-R. Zeng, Q.-Y. Luo and Y.-P. Xu

The title complex, [Mn(C₂₀H₁₄N₂O₂)], is a mononuclear manganese(II) compound. The manganese(II) ion is four-coordinated in a square-planar geometry by two imine N and two phenolate O atoms from one 2,2'-[o-phenylenebis(nitrilomethylidyne)]diphenolate Schiff base ligand. No strong hydrogen bonds were found in the crystal structure.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807052993/hg2322sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807052993/hg2322Isup2.hkl Contains datablock I

CCDC reference: 1284448

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.010 Å
R factor = 0.059
wR factor = 0.161
Data-to-parameter ratio = 12.9

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.16
PLAT341_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...         10

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           25.50
           From the CIF: _reflns_number_total               2930
           Count of symmetry unique reflns         1726
           Completeness (_total/calc)            169.76%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      1204
           Fraction of Friedel pairs measured     0.698
           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
PLAT794_ALERT_5_G Check Predicted Bond Valency for Mn1         (3)       3.54

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

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 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
   1 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

Comment top

The X-ray structure determination shows the title complex to be a discrete molecular compound (Fig.1). Each manganese(II) ion is four-coordinated in a square-planar geometry by two imine N and two phenolate O atoms from one 2,2'-[o-phenylenebis(nitrilomethylidyne)]- diphenolate Schiff base ligand, coordination bond length are listed as: Mn1—N1 1.853 (5) Å; Mn1—N2 1.852 (5) Å; Mn1—O1 1.834 (4) Å; Mn1—O2 1.841 (4) Å. Atom O1, O2, N1 and N2 are approximately coplanar with the central Mn cation, the maximum deviation from the least-squares plane through all five atoms being 0.0141 Å for atom O1. The structure of a related complex, ZnC₂₀H₁₄N₂O₂ has been reported (Liu et al., 2007). No strong hydrogen bonds are found with the the three-dimensional framework of the crystal mainly constructed by weak intermolecular interactions.

Related literature top

For related literature, see: Liu et al. (2007).

Experimental top

A mixture of 2,2'-[o-phenylenebis(nitrilomethylidyne)]- diphenolate Schiff base (0.341 g, 0.001 mol)and MnSO₄.H₂O (0.169 g, 0.001 mol) in the More ratio of 1:1 was added to methanol, The mixture was heated at 365 K or so for 5 h under reflux with stirring.The resulting solution was then filtered off. Single crystals suitable for X-ray diffraction analysis formed after a week by slow evaporation of the solvent.

Structure description top

For related literature, see: Liu et al. (2007).

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Siemens, 1996); software used to prepare material for publication: SHELXTL (Siemens, 1996).

Figures top

	Fig. 1. The asymmetric unit of (I), showing atom labelling and 50% probability displacement ellipsoids for the non-hydrogen atoms.
	Fig. 2. The packing diagram of (I), viewed along the a axis.

{2,2'-[o-Phenylenebis(nitrilomethylidyne)]diphenolato}manganese(II) top

Crystal data top

[Mn(C₂₀H₁₄N₂O₂)]	F(000) = 756.0
M_r = 369.27	D_x = 1.558 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 3944 reflections
a = 5.4676 (6) Å	θ = 1.0–28.3°
b = 16.6244 (19) Å	µ = 0.85 mm⁻¹
c = 17.324 (2) Å	T = 293 K
V = 1574.7 (3) Å³	Block, brown
Z = 4	0.25 × 0.08 × 0.07 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	2298 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.046
Graphite monochromator	θ_max = 25.5°, θ_min = 1.7°
φ and ω scans	h = −6→6
9864 measured reflections	k = −20→20
2930 independent reflections	l = −20→20

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.059	w = 1/[σ²(F_o²) + (0.0556P)² + 2.0762P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.161	(Δ/σ)_max < 0.001
S = 1.06	Δρ_max = 0.81 e Å⁻³
2930 reflections	Δρ_min = −0.37 e Å⁻³
227 parameters	Extinction correction: SHELXL97 (Sheldrick, 1997), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.020 (3)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983)
Secondary atom site location: difference Fourier map	Absolute structure parameter: −0.13 (5)

Crystal data top

[Mn(C₂₀H₁₄N₂O₂)]	V = 1574.7 (3) Å³
M_r = 369.27	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 5.4676 (6) Å	µ = 0.85 mm⁻¹
b = 16.6244 (19) Å	T = 293 K
c = 17.324 (2) Å	0.25 × 0.08 × 0.07 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	2298 reflections with I > 2σ(I)
9864 measured reflections	R_int = 0.046
2930 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.059	H-atom parameters constrained
wR(F²) = 0.161	Δρ_max = 0.81 e Å⁻³
S = 1.06	Δρ_min = −0.37 e Å⁻³
2930 reflections	Absolute structure: Flack (1983)
227 parameters	Absolute structure parameter: −0.13 (5)
0 restraints

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

	x	y	z	U_iso*/U_eq
Mn1	0.15024 (15)	0.77722 (5)	0.31030 (4)	0.0471 (3)
O1	0.1505 (9)	0.8737 (2)	0.3616 (2)	0.0654 (11)
O2	0.4255 (9)	0.8173 (2)	0.2628 (2)	0.0626 (12)
N1	−0.1267 (10)	0.7379 (3)	0.3591 (3)	0.0609 (13)
N2	0.1512 (11)	0.6815 (3)	0.2556 (3)	0.0602 (13)
C1	−0.0151 (14)	0.9022 (4)	0.4090 (4)	0.0649 (17)
C2	0.0095 (13)	0.9814 (4)	0.4377 (4)	0.0660 (17)
H2	0.1447	1.0119	0.4235	0.079*
C3	−0.1621 (14)	1.0137 (4)	0.4859 (4)	0.0668 (16)
H3	−0.1421	1.0664	0.5028	0.080*
C4	−0.3658 (14)	0.9706 (4)	0.5105 (4)	0.0674 (17)
H4	−0.4777	0.9933	0.5446	0.081*
C5	−0.3974 (13)	0.8939 (4)	0.4834 (4)	0.0664 (18)
H5	−0.5348	0.8648	0.4982	0.080*
C6	−0.2241 (13)	0.8582 (4)	0.4332 (4)	0.0648 (17)
C7	−0.2680 (13)	0.7784 (4)	0.4071 (3)	0.0625 (15)
H7	−0.4076	0.7527	0.4253	0.075*
C8	−0.1898 (13)	0.6582 (4)	0.3369 (4)	0.0616 (16)
C9	−0.3811 (13)	0.6121 (4)	0.3653 (4)	0.0635 (16)
H9	−0.4812	0.6321	0.4042	0.076*
C10	−0.4224 (13)	0.5357 (4)	0.3353 (4)	0.0648 (17)
H10	−0.5559	0.5057	0.3520	0.078*
C11	−0.2629 (14)	0.5040 (4)	0.2800 (4)	0.0649 (17)
H11	−0.2875	0.4521	0.2617	0.078*
C12	−0.0690 (14)	0.5489 (4)	0.2523 (4)	0.0636 (17)
H12	0.0362	0.5275	0.2155	0.076*
C13	−0.0334 (13)	0.6267 (4)	0.2803 (4)	0.0615 (16)
C14	0.2948 (12)	0.6644 (4)	0.1966 (4)	0.0618 (16)
H14	0.2688	0.6156	0.1717	0.074*
C15	0.4841 (13)	0.7136 (4)	0.1683 (4)	0.0639 (16)
C16	0.6217 (13)	0.6860 (4)	0.1047 (4)	0.0657 (17)
H16	0.5813	0.6371	0.0820	0.079*
C17	0.8115 (12)	0.7291 (4)	0.0758 (4)	0.0670 (16)
H17	0.8961	0.7108	0.0327	0.080*
C18	0.8798 (14)	0.8022 (4)	0.1118 (4)	0.0663 (17)
H18	1.0134	0.8312	0.0936	0.080*
C19	0.7471 (13)	0.8303 (4)	0.1739 (4)	0.0650 (17)
H19	0.7913	0.8789	0.1965	0.078*
C20	0.5471 (13)	0.7875 (4)	0.2040 (4)	0.0632 (16)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Mn1	0.0554 (5)	0.0423 (4)	0.0437 (4)	0.0039 (4)	−0.0010 (4)	0.0021 (3)
O1	0.075 (3)	0.056 (2)	0.065 (3)	−0.003 (2)	0.009 (3)	−0.0109 (19)
O2	0.067 (3)	0.057 (2)	0.064 (3)	0.000 (2)	0.010 (2)	0.001 (2)
N1	0.068 (3)	0.055 (3)	0.059 (3)	−0.003 (3)	0.009 (3)	−0.004 (2)
N2	0.070 (3)	0.052 (3)	0.058 (3)	0.001 (3)	0.006 (3)	−0.005 (2)
C1	0.075 (5)	0.056 (4)	0.064 (4)	−0.001 (3)	0.008 (4)	−0.010 (3)
C2	0.076 (4)	0.057 (3)	0.065 (4)	0.000 (3)	0.007 (4)	−0.010 (3)
C3	0.077 (4)	0.058 (3)	0.065 (4)	0.001 (4)	0.007 (4)	−0.010 (3)
C4	0.076 (5)	0.060 (4)	0.066 (4)	0.001 (4)	0.008 (4)	−0.009 (3)
C5	0.074 (5)	0.060 (4)	0.065 (4)	0.001 (3)	0.008 (3)	−0.008 (3)
C6	0.073 (4)	0.058 (4)	0.063 (4)	0.000 (3)	0.008 (3)	−0.007 (3)
C7	0.069 (4)	0.058 (3)	0.061 (3)	−0.001 (4)	0.009 (3)	−0.005 (3)
C8	0.070 (4)	0.054 (3)	0.060 (3)	−0.004 (3)	0.006 (3)	−0.003 (3)
C9	0.072 (4)	0.056 (3)	0.063 (4)	−0.005 (3)	0.005 (3)	−0.002 (3)
C10	0.074 (5)	0.056 (4)	0.064 (4)	−0.006 (3)	0.005 (3)	−0.003 (3)
C11	0.075 (4)	0.055 (4)	0.065 (4)	−0.005 (3)	0.004 (3)	−0.004 (3)
C12	0.074 (5)	0.054 (3)	0.063 (4)	−0.004 (3)	0.004 (3)	−0.004 (3)
C13	0.072 (4)	0.053 (3)	0.060 (3)	−0.003 (3)	0.004 (3)	−0.004 (3)
C14	0.071 (4)	0.055 (3)	0.059 (3)	0.003 (3)	0.007 (3)	−0.005 (3)
C15	0.071 (4)	0.059 (4)	0.062 (4)	0.004 (3)	0.008 (3)	0.000 (3)
C16	0.072 (5)	0.062 (4)	0.063 (4)	0.004 (4)	0.009 (4)	0.000 (3)
C17	0.072 (4)	0.064 (4)	0.065 (4)	0.005 (4)	0.010 (3)	0.002 (3)
C18	0.070 (4)	0.063 (4)	0.065 (4)	0.004 (3)	0.011 (4)	0.004 (3)
C19	0.069 (4)	0.061 (4)	0.065 (4)	0.003 (3)	0.011 (3)	0.003 (3)
C20	0.068 (4)	0.058 (4)	0.063 (4)	0.002 (3)	0.010 (3)	0.002 (3)

Geometric parameters (Å, º) top

Mn1—O1	1.834 (4)	C8—C9	1.387 (9)
Mn1—O2	1.841 (4)	C8—C13	1.402 (9)
Mn1—N2	1.852 (5)	C9—C10	1.390 (9)
Mn1—N1	1.853 (5)	C9—H9	0.9300
O1—C1	1.310 (7)	C10—C11	1.399 (9)
O2—C20	1.314 (7)	C10—H10	0.9300
N1—C7	1.320 (7)	C11—C12	1.383 (9)
N1—C8	1.422 (8)	C11—H11	0.9300
N2—C14	1.320 (8)	C12—C13	1.396 (8)
N2—C13	1.425 (8)	C12—H12	0.9300
C1—C2	1.414 (9)	C14—C15	1.408 (9)
C1—C6	1.419 (10)	C14—H14	0.9300
C2—C3	1.366 (9)	C15—C16	1.410 (9)
C2—H2	0.9300	C15—C20	1.418 (9)
C3—C4	1.392 (9)	C16—C17	1.357 (9)
C3—H3	0.9300	C16—H16	0.9300
C4—C5	1.369 (8)	C17—C18	1.416 (9)
C4—H4	0.9300	C17—H17	0.9300
C5—C6	1.417 (9)	C18—C19	1.379 (9)
C5—H5	0.9300	C18—H18	0.9300
C6—C7	1.422 (9)	C19—C20	1.405 (9)
C7—H7	0.9300	C19—H19	0.9300

O1—Mn1—O2	84.2 (2)	C13—C8—N1	112.8 (6)
O1—Mn1—N2	178.2 (2)	C8—C9—C10	119.7 (6)
O2—Mn1—N2	94.6 (2)	C8—C9—H9	120.2
O1—Mn1—N1	95.1 (2)	C10—C9—H9	120.2
O2—Mn1—N1	179.3 (2)	C9—C10—C11	119.9 (6)
N2—Mn1—N1	86.1 (2)	C9—C10—H10	120.0
C1—O1—Mn1	128.2 (4)	C11—C10—H10	120.0
C20—O2—Mn1	128.6 (4)	C12—C11—C10	120.8 (6)
C7—N1—C8	120.2 (6)	C12—C11—H11	119.6
C7—N1—Mn1	125.8 (4)	C10—C11—H11	119.6
C8—N1—Mn1	113.8 (4)	C11—C12—C13	119.1 (6)
C14—N2—C13	121.1 (5)	C11—C12—H12	120.4
C14—N2—Mn1	125.6 (4)	C13—C12—H12	120.4
C13—N2—Mn1	113.2 (4)	C12—C13—C8	120.2 (6)
O1—C1—C2	119.4 (6)	C12—C13—N2	125.9 (6)
O1—C1—C6	123.7 (6)	C8—C13—N2	113.8 (5)
C2—C1—C6	116.9 (6)	N2—C14—C15	125.6 (6)
C3—C2—C1	121.0 (7)	N2—C14—H14	117.2
C3—C2—H2	119.5	C15—C14—H14	117.2
C1—C2—H2	119.5	C14—C15—C16	118.4 (6)
C2—C3—C4	122.3 (6)	C14—C15—C20	122.0 (6)
C2—C3—H3	118.8	C16—C15—C20	119.5 (6)
C4—C3—H3	118.8	C17—C16—C15	121.6 (6)
C5—C4—C3	118.4 (7)	C17—C16—H16	119.2
C5—C4—H4	120.8	C15—C16—H16	119.2
C3—C4—H4	120.8	C16—C17—C18	119.6 (6)
C4—C5—C6	121.1 (7)	C16—C17—H17	120.2
C4—C5—H5	119.5	C18—C17—H17	120.2
C6—C5—H5	119.5	C19—C18—C17	119.6 (7)
C5—C6—C1	120.3 (6)	C19—C18—H18	120.2
C5—C6—C7	118.2 (6)	C17—C18—H18	120.2
C1—C6—C7	121.5 (6)	C18—C19—C20	121.9 (7)
N1—C7—C6	125.3 (6)	C18—C19—H19	119.1
N1—C7—H7	117.4	C20—C19—H19	119.1
C6—C7—H7	117.4	O2—C20—C19	119.3 (6)
C9—C8—C13	120.1 (6)	O2—C20—C15	122.9 (6)
C9—C8—N1	127.0 (6)	C19—C20—C15	117.8 (6)

Experimental details

Crystal data
Chemical formula	[Mn(C₂₀H₁₄N₂O₂)]
M_r	369.27
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	293
a, b, c (Å)	5.4676 (6), 16.6244 (19), 17.324 (2)
V (Å³)	1574.7 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.85
Crystal size (mm)	0.25 × 0.08 × 0.07

Data collection
Diffractometer	Bruker SMART CCD area-detector
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	9864, 2930, 2298
R_int	0.046
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.059, 0.161, 1.06
No. of reflections	2930
No. of parameters	227
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.81, −0.37
Absolute structure	Flack (1983)
Absolute structure parameter	−0.13 (5)

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Siemens, 1996).

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Retracted: {2,2'-[o-Phenyl­enebis(nitrilo­methyl­idyne)]diphenolato}manganese(II)

Supporting information

Key indicators

checkCIF/PLATON results

Retracted: {2,2'-[o-Phenylenebis(nitrilomethylidyne)]diphenolato}manganese(II)