Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807052993/hg2322sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807052993/hg2322Isup2.hkl |
CCDC reference: 1284448
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.
All H atoms were located at calculated positions and refined as riding on their parent C atoms with the C—H bond length fixed to 0.93 Å with Uiso(H) = 1.2 times Ueq(C).
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.
For related literature, see: Liu et al. (2007).
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).
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. |
[Mn(C20H14N2O2)] | F(000) = 756.0 |
Mr = 369.27 | Dx = 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 |
Bruker SMART CCD area-detector diffractometer | 2298 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.046 |
Graphite monochromator | θmax = 25.5°, θmin = 1.7° |
φ and ω scans | h = −6→6 |
9864 measured reflections | k = −20→20 |
2930 independent reflections | l = −20→20 |
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(Fo2) + (0.0556P)2 + 2.0762P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.161 | (Δ/σ)max < 0.001 |
S = 1.06 | Δρmax = 0.81 e Å−3 |
2930 reflections | Δρmin = −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) |
[Mn(C20H14N2O2)] | V = 1574.7 (3) Å3 |
Mr = 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 |
Bruker SMART CCD area-detector diffractometer | 2298 reflections with I > 2σ(I) |
9864 measured reflections | Rint = 0.046 |
2930 independent reflections |
R[F2 > 2σ(F2)] = 0.059 | H-atom parameters constrained |
wR(F2) = 0.161 | Δρmax = 0.81 e Å−3 |
S = 1.06 | Δρmin = −0.37 e Å−3 |
2930 reflections | Absolute structure: Flack (1983) |
227 parameters | Absolute structure parameter: −0.13 (5) |
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 | ||
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) |
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) |
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)] |
Mr | 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 |
Rint | 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 |
Δρmax, Δρmin (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).
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.