Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807035076/at2344sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807035076/at2344Isup2.hkl |
CCDC reference: 1270870
Manganese dinitrate hexahydrate (144 mg, 0.5 mmol), phen (198 mg, 1 mmol) and dihydroxy glyoxime (120 mg, 1 mmol) were dissolved in ethanol (15 ml). The mixture was heated for 5 h under reflux with stirring. It was then filtered to give a clear solution, into which diethyl ether vapour was allowed to condense in a closed vessel. After being allowed to stand for a few days at room temperature, some colourless single crystals suitable for X-ray diffraction analysis precipitated.
H atoms of the water molecules were located in a difference synthesis and refined freely. The remaining H atoms were positioned geometrically, with O—H = 0.82 Å (for OH) and C—H = 0.93 Å for aromatic H, and constrained to ride on their parent atoms, with Uiso(H) = xUeq(C, O), where x = 1.2 for aromatic H atoms and x = 1.5 for hydroxyl H atoms.
The crystal structure of bis(1,10-phenanthroline-N,N')(dihydroxy glyoxime) copper(II) dinitrate dihydrate, (II), and bis(1,10-phenanthroline-N,N') (dihydroxy glyoxime) cobalt(II) dinitrate dihydrate, (III), has previously been reported (Liu et al., 2007). The crystal structure determination of the title compound, (I), has been carried out in order to elucidate the molecular conformation and to compare it with that of (II) and (III). We report herein the crystal structure of (I).
In the molecule of (I) (Fig. 1), the ligand bond lengths and angles are within normal ranges (Allen et al., 1987). The six N atoms of one dihydroxy glyoxime and two 1,10-phenanthroline (phen) ligands are coordinated to the Mn atom, in a distorted octahedral arrangement (Table 1). The dihydroxy glyoxime and two phen ligands are each planar and the phen ligands are nearly perpendicular to each other, with a dihedral angle of 86.94 (7)°, as in (II) and (III).
In the crystal structure, the molecules are linked into a three-dimensional framework (Fig. 2) by O—H···O, C—H···O, C—H···N and O—H···N hydrogen bonds (Table 2). There are π-π stacking interactions between adjacent phen ligands with centroid-centroid distance of 3.580 (2) Å (symmetry code: 1 - x, 2 - y, -z). These π-π stacking interactions and hydrogen bonds lead to a supramolecular network structure (Fig. 2), as in (II) and (III). The three compounds, (I), (II) and (III), are isostructural.
For a related structure, see: Liu et al. (2007). For bond-length data, see: Allen et al. (1987).
Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; 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.
[Mn(C12H8N2)2(C2H4N2O4)](NO3)2·2H2O | F(000) = 1428 |
Mr = 695.47 | Dx = 1.535 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 5592 reflections |
a = 13.913 (2) Å | θ = 2.1–25.0° |
b = 11.998 (5) Å | µ = 0.52 mm−1 |
c = 18.131 (3) Å | T = 273 K |
β = 96.228 (4)° | Prism, colourless |
V = 3008.6 (14) Å3 | 0.30 × 0.23 × 0.18 mm |
Z = 4 |
Bruker APEX II area-detector diffractometer | 6179 independent reflections |
Radiation source: fine-focus sealed tube | 3132 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.041 |
φ and ω scans | θmax = 26.7°, θmin = 2.0° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −17→17 |
Tmin = 0.861, Tmax = 0.912 | k = −15→15 |
20095 measured reflections | l = −22→22 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.051 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.166 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.99 | w = 1/[σ2(Fo2) + (0.0806P)2] where P = (Fo2 + 2Fc2)/3 |
6179 reflections | (Δ/σ)max = 0.001 |
444 parameters | Δρmax = 0.65 e Å−3 |
12 restraints | Δρmin = −0.49 e Å−3 |
[Mn(C12H8N2)2(C2H4N2O4)](NO3)2·2H2O | V = 3008.6 (14) Å3 |
Mr = 695.47 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 13.913 (2) Å | µ = 0.52 mm−1 |
b = 11.998 (5) Å | T = 273 K |
c = 18.131 (3) Å | 0.30 × 0.23 × 0.18 mm |
β = 96.228 (4)° |
Bruker APEX II area-detector diffractometer | 6179 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 3132 reflections with I > 2σ(I) |
Tmin = 0.861, Tmax = 0.912 | Rint = 0.041 |
20095 measured reflections |
R[F2 > 2σ(F2)] = 0.051 | 12 restraints |
wR(F2) = 0.166 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.99 | Δρmax = 0.65 e Å−3 |
6179 reflections | Δρmin = −0.49 e Å−3 |
444 parameters |
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 | 0.77582 (4) | 0.75577 (4) | 0.03825 (3) | 0.03420 (19) | |
O1 | 0.7959 (2) | 0.9968 (2) | 0.04742 (16) | 0.0605 (8) | |
H1A | 0.8019 | 0.9977 | 0.0029 | 0.091* | |
O2 | 0.8357 (2) | 0.6023 (3) | 0.14815 (18) | 0.0683 (9) | |
H2A | 0.8150 | 0.5969 | 0.1887 | 0.102* | |
O3 | 0.9306 (4) | 0.7550 (5) | 0.2469 (3) | 0.1472 (19) | |
H3A | 0.9890 | 0.7641 | 0.2467 | 0.221* | |
O4 | 0.9029 (4) | 0.9960 (4) | 0.1826 (4) | 0.155 (2) | |
H4A | 0.9502 | 0.9809 | 0.2120 | 0.233* | |
O5 | 0.7738 (3) | 0.1306 (3) | 0.9096 (2) | 0.0962 (13) | |
O6 | 0.8934 (2) | 0.0146 (3) | 0.9287 (2) | 0.0783 (10) | |
O7 | 0.8897 (4) | 0.1357 (4) | 0.8427 (3) | 0.1356 (19) | |
O8 | 0.7404 (6) | 0.8835 (8) | 0.2850 (4) | 0.219 (4) | |
O9 | 0.6159 (6) | 0.8842 (6) | 0.3345 (4) | 0.209 (3) | |
O10 | 0.6416 (8) | 1.0073 (6) | 0.2609 (6) | 0.388 (11) | |
O11 | 0.5552 (13) | 0.4230 (13) | 0.1434 (9) | 0.574 (14) | |
O12 | 0.695 (2) | 0.3357 (18) | 0.2000 (11) | 0.64 (2) | |
N1 | 0.6533 (2) | 0.7803 (3) | 0.0767 (2) | 0.0492 (9) | |
N2 | 0.7067 (2) | 0.8181 (3) | −0.05277 (19) | 0.0453 (9) | |
N3 | 0.7384 (2) | 0.6057 (3) | 0.00436 (19) | 0.0495 (9) | |
N4 | 0.8938 (2) | 0.7246 (3) | −0.00697 (18) | 0.0459 (9) | |
N5 | 0.8376 (2) | 0.7049 (3) | 0.1295 (2) | 0.0490 (9) | |
N6 | 0.8222 (2) | 0.8935 (3) | 0.0762 (2) | 0.0473 (9) | |
N7 | 0.8510 (3) | 0.0927 (4) | 0.8919 (3) | 0.0713 (12) | |
N8 | 0.6670 (6) | 0.9299 (9) | 0.2896 (5) | 0.155 (4) | |
C1 | 0.6298 (3) | 0.7618 (4) | 0.1438 (3) | 0.0601 (12) | |
H1 | 0.6769 | 0.7353 | 0.1798 | 0.072* | |
C2 | 0.5368 (4) | 0.7804 (4) | 0.1633 (3) | 0.0707 (14) | |
H2 | 0.5236 | 0.7678 | 0.2118 | 0.085* | |
C3 | 0.4665 (3) | 0.8164 (4) | 0.1125 (3) | 0.0666 (14) | |
H3 | 0.4042 | 0.8270 | 0.1253 | 0.080* | |
C4 | 0.4872 (3) | 0.8374 (3) | 0.0413 (3) | 0.0570 (12) | |
C5 | 0.4199 (3) | 0.8792 (4) | −0.0160 (3) | 0.0690 (14) | |
H5 | 0.3561 | 0.8914 | −0.0074 | 0.083* | |
C6 | 0.4483 (4) | 0.9013 (4) | −0.0837 (3) | 0.0729 (15) | |
H6 | 0.4035 | 0.9295 | −0.1208 | 0.088* | |
C7 | 0.5460 (3) | 0.8824 (4) | −0.0996 (3) | 0.0575 (12) | |
C8 | 0.5799 (4) | 0.9054 (4) | −0.1654 (3) | 0.0720 (15) | |
H8 | 0.5382 | 0.9344 | −0.2043 | 0.086* | |
C9 | 0.6765 (4) | 0.8862 (4) | −0.1753 (3) | 0.0742 (15) | |
H9 | 0.6999 | 0.9041 | −0.2200 | 0.089* | |
C10 | 0.7378 (3) | 0.8397 (3) | −0.1172 (3) | 0.0562 (12) | |
H10 | 0.8016 | 0.8238 | −0.1242 | 0.067* | |
C11 | 0.6126 (3) | 0.8395 (3) | −0.0444 (2) | 0.0468 (10) | |
C12 | 0.5836 (3) | 0.8180 (3) | 0.0252 (2) | 0.0459 (10) | |
C13 | 0.6605 (3) | 0.5457 (4) | 0.0147 (3) | 0.0667 (13) | |
H13 | 0.6140 | 0.5755 | 0.0422 | 0.080* | |
C14 | 0.6478 (4) | 0.4399 (4) | −0.0147 (3) | 0.0818 (17) | |
H14 | 0.5931 | 0.3993 | −0.0065 | 0.098* | |
C15 | 0.7135 (4) | 0.3950 (4) | −0.0549 (3) | 0.0762 (15) | |
H15 | 0.7036 | 0.3244 | −0.0755 | 0.091* | |
C16 | 0.7964 (3) | 0.4549 (3) | −0.0657 (2) | 0.0542 (12) | |
C17 | 0.8730 (4) | 0.4158 (4) | −0.1057 (3) | 0.0659 (14) | |
H17 | 0.8670 | 0.3463 | −0.1285 | 0.079* | |
C18 | 0.9528 (4) | 0.4755 (4) | −0.1116 (2) | 0.0607 (13) | |
H18 | 1.0010 | 0.4465 | −0.1377 | 0.073* | |
C19 | 0.9653 (3) | 0.5827 (4) | −0.0786 (2) | 0.0488 (10) | |
C20 | 1.0468 (3) | 0.6503 (4) | −0.0802 (2) | 0.0591 (12) | |
H20 | 1.0987 | 0.6262 | −0.1043 | 0.071* | |
C21 | 1.0498 (3) | 0.7506 (4) | −0.0466 (2) | 0.0591 (12) | |
H21 | 1.1040 | 0.7957 | −0.0478 | 0.071* | |
C22 | 0.9729 (3) | 0.7873 (3) | −0.0101 (2) | 0.0516 (11) | |
H22 | 0.9765 | 0.8569 | 0.0127 | 0.062* | |
C23 | 0.8909 (3) | 0.6235 (3) | −0.0409 (2) | 0.0461 (10) | |
C24 | 0.8064 (3) | 0.5585 (3) | −0.0346 (2) | 0.0463 (10) | |
C25 | 0.8807 (3) | 0.7818 (4) | 0.1722 (2) | 0.0509 (11) | |
C26 | 0.8680 (3) | 0.8923 (4) | 0.1413 (3) | 0.0533 (11) | |
H11A | 0.511 (3) | 0.401 (3) | 0.111 (3) | 0.570 (13)* | |
H12A | 0.674 (8) | 0.286 (4) | 0.228 (5) | 0.64 (3)* | |
H11B | 0.5599 (19) | 0.4908 (14) | 0.1538 (16) | 0.573 (7)* | |
H12B | 0.731 (2) | 0.307 (3) | 0.1701 (18) | 0.642 (10)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Mn1 | 0.0323 (3) | 0.0334 (3) | 0.0362 (3) | 0.0025 (3) | 0.0005 (2) | −0.0023 (3) |
O1 | 0.075 (2) | 0.0436 (17) | 0.061 (2) | 0.0081 (14) | −0.0009 (18) | 0.0001 (15) |
O2 | 0.075 (2) | 0.063 (2) | 0.066 (2) | 0.0010 (16) | 0.0004 (18) | 0.0183 (17) |
O3 | 0.143 (4) | 0.182 (5) | 0.106 (4) | 0.004 (4) | −0.031 (3) | 0.020 (3) |
O4 | 0.175 (6) | 0.125 (4) | 0.155 (5) | −0.013 (3) | −0.026 (4) | −0.042 (4) |
O5 | 0.067 (2) | 0.104 (3) | 0.120 (3) | 0.020 (2) | 0.021 (2) | 0.006 (2) |
O6 | 0.078 (2) | 0.059 (2) | 0.096 (3) | 0.0090 (18) | 0.003 (2) | 0.018 (2) |
O7 | 0.134 (4) | 0.147 (4) | 0.136 (4) | 0.028 (3) | 0.058 (3) | 0.064 (3) |
O8 | 0.168 (6) | 0.293 (10) | 0.204 (8) | −0.064 (7) | 0.058 (6) | −0.083 (6) |
O9 | 0.229 (9) | 0.218 (8) | 0.175 (7) | 0.002 (6) | 0.000 (6) | −0.022 (6) |
O10 | 0.55 (2) | 0.142 (6) | 0.380 (14) | −0.070 (8) | −0.355 (14) | 0.128 (7) |
O11 | 0.55 (3) | 0.76 (3) | 0.48 (3) | 0.09 (3) | 0.39 (2) | 0.16 (2) |
O12 | 0.56 (3) | 0.94 (5) | 0.40 (3) | 0.04 (3) | −0.09 (2) | −0.40 (3) |
N1 | 0.048 (2) | 0.044 (2) | 0.055 (2) | 0.0009 (15) | 0.0006 (18) | −0.0012 (17) |
N2 | 0.052 (2) | 0.039 (2) | 0.044 (2) | 0.0024 (15) | 0.0001 (17) | −0.0074 (16) |
N3 | 0.046 (2) | 0.048 (2) | 0.054 (2) | −0.0017 (17) | 0.0016 (17) | −0.0013 (18) |
N4 | 0.046 (2) | 0.040 (2) | 0.050 (2) | 0.0034 (15) | −0.0021 (16) | −0.0018 (16) |
N5 | 0.046 (2) | 0.047 (2) | 0.054 (2) | 0.0020 (16) | 0.0027 (17) | 0.0055 (19) |
N6 | 0.045 (2) | 0.046 (2) | 0.050 (2) | 0.0041 (16) | 0.0028 (17) | 0.0006 (17) |
N7 | 0.063 (3) | 0.069 (3) | 0.082 (4) | −0.006 (2) | 0.010 (2) | 0.010 (3) |
N8 | 0.108 (6) | 0.245 (12) | 0.116 (7) | −0.070 (7) | 0.031 (5) | −0.083 (7) |
C1 | 0.055 (3) | 0.074 (3) | 0.052 (3) | 0.007 (2) | 0.007 (2) | 0.009 (3) |
C2 | 0.061 (3) | 0.082 (4) | 0.070 (4) | 0.006 (3) | 0.013 (3) | −0.003 (3) |
C3 | 0.049 (3) | 0.068 (3) | 0.086 (4) | −0.004 (2) | 0.022 (3) | −0.012 (3) |
C4 | 0.044 (3) | 0.046 (3) | 0.079 (4) | 0.002 (2) | −0.002 (2) | −0.010 (2) |
C5 | 0.048 (3) | 0.067 (3) | 0.090 (4) | 0.007 (2) | −0.003 (3) | −0.006 (3) |
C6 | 0.061 (3) | 0.061 (3) | 0.090 (4) | 0.012 (2) | −0.022 (3) | −0.004 (3) |
C7 | 0.061 (3) | 0.052 (3) | 0.057 (3) | 0.005 (2) | −0.009 (2) | −0.003 (2) |
C8 | 0.077 (4) | 0.064 (3) | 0.069 (4) | 0.012 (3) | −0.019 (3) | −0.002 (3) |
C9 | 0.108 (5) | 0.058 (3) | 0.053 (3) | 0.002 (3) | −0.005 (3) | −0.006 (3) |
C10 | 0.070 (3) | 0.053 (3) | 0.045 (3) | 0.002 (2) | 0.002 (2) | −0.003 (2) |
C11 | 0.047 (3) | 0.038 (2) | 0.052 (3) | 0.0021 (19) | −0.005 (2) | −0.001 (2) |
C12 | 0.042 (2) | 0.038 (2) | 0.056 (3) | 0.0024 (18) | 0.000 (2) | −0.003 (2) |
C13 | 0.055 (3) | 0.052 (3) | 0.094 (4) | −0.009 (2) | 0.010 (3) | −0.004 (3) |
C14 | 0.066 (3) | 0.054 (3) | 0.125 (5) | −0.015 (3) | 0.012 (3) | −0.009 (3) |
C15 | 0.078 (4) | 0.047 (3) | 0.101 (5) | −0.006 (3) | −0.002 (3) | −0.015 (3) |
C16 | 0.064 (3) | 0.039 (2) | 0.057 (3) | 0.005 (2) | −0.005 (2) | −0.003 (2) |
C17 | 0.093 (4) | 0.053 (3) | 0.049 (3) | 0.018 (3) | −0.005 (3) | −0.007 (2) |
C18 | 0.077 (3) | 0.058 (3) | 0.046 (3) | 0.021 (3) | 0.002 (2) | −0.006 (2) |
C19 | 0.050 (3) | 0.054 (3) | 0.041 (3) | 0.013 (2) | 0.000 (2) | 0.004 (2) |
C20 | 0.054 (3) | 0.073 (3) | 0.052 (3) | 0.015 (2) | 0.012 (2) | 0.003 (3) |
C21 | 0.048 (3) | 0.068 (3) | 0.062 (3) | −0.001 (2) | 0.006 (2) | 0.003 (3) |
C22 | 0.044 (3) | 0.051 (2) | 0.059 (3) | 0.000 (2) | 0.002 (2) | −0.003 (2) |
C23 | 0.047 (2) | 0.046 (2) | 0.043 (3) | 0.007 (2) | −0.0049 (19) | 0.003 (2) |
C24 | 0.053 (3) | 0.042 (2) | 0.042 (3) | 0.009 (2) | −0.002 (2) | 0.000 (2) |
C25 | 0.045 (2) | 0.060 (3) | 0.046 (3) | 0.004 (2) | −0.001 (2) | 0.002 (2) |
C26 | 0.052 (3) | 0.057 (3) | 0.051 (3) | −0.002 (2) | 0.001 (2) | −0.011 (2) |
Mn1—N1 | 1.933 (3) | C3—C4 | 1.376 (6) |
Mn1—N2 | 1.966 (3) | C3—H3 | 0.9300 |
Mn1—N3 | 1.955 (3) | C4—C5 | 1.414 (6) |
Mn1—N4 | 1.949 (3) | C4—C12 | 1.421 (5) |
Mn1—N5 | 1.881 (4) | C5—C6 | 1.355 (7) |
Mn1—N6 | 1.877 (3) | C5—H5 | 0.9300 |
O1—N6 | 1.378 (4) | C6—C7 | 1.437 (7) |
O1—H1A | 0.8200 | C6—H6 | 0.9300 |
O2—N5 | 1.278 (4) | C7—C8 | 1.359 (6) |
O2—H2A | 0.8200 | C7—C11 | 1.387 (6) |
O3—C25 | 1.488 (6) | C8—C9 | 1.395 (7) |
O3—H3A | 0.8200 | C8—H8 | 0.9300 |
O4—C26 | 1.505 (6) | C9—C10 | 1.398 (6) |
O4—H4A | 0.8200 | C9—H9 | 0.9300 |
O5—N7 | 1.240 (5) | C10—H10 | 0.9300 |
O6—N7 | 1.259 (5) | C11—C12 | 1.390 (6) |
O7—N7 | 1.207 (5) | C13—C14 | 1.380 (6) |
O8—N8 | 1.174 (9) | C13—H13 | 0.9300 |
O9—N8 | 1.262 (8) | C14—C15 | 1.342 (6) |
O10—N8 | 1.104 (11) | C14—H14 | 0.9300 |
O11—H11A | 0.85 (5) | C15—C16 | 1.390 (6) |
O11—H11B | 0.836 (10) | C15—H15 | 0.9300 |
O12—H12A | 0.86 (8) | C16—C24 | 1.366 (5) |
O12—H12B | 0.85 (4) | C16—C17 | 1.432 (6) |
N1—C1 | 1.313 (5) | C17—C18 | 1.335 (6) |
N1—C12 | 1.349 (5) | C17—H17 | 0.9300 |
N2—C10 | 1.315 (5) | C18—C19 | 1.420 (6) |
N2—C11 | 1.358 (5) | C18—H18 | 0.9300 |
N3—C13 | 1.331 (5) | C19—C23 | 1.390 (5) |
N3—C24 | 1.363 (5) | C19—C20 | 1.397 (6) |
N4—C22 | 1.340 (5) | C20—C21 | 1.348 (6) |
N4—C23 | 1.358 (5) | C20—H20 | 0.9300 |
N5—C25 | 1.308 (5) | C21—C22 | 1.389 (5) |
N6—C26 | 1.280 (5) | C21—H21 | 0.9300 |
C1—C2 | 1.395 (6) | C22—H22 | 0.9300 |
C1—H1 | 0.9300 | C23—C24 | 1.427 (5) |
C2—C3 | 1.339 (7) | C25—C26 | 1.443 (6) |
C2—H2 | 0.9300 | ||
N1—Mn1—N2 | 82.79 (15) | C7—C6—H6 | 119.2 |
N1—Mn1—N3 | 92.23 (14) | C8—C7—C11 | 116.2 (5) |
N1—Mn1—N4 | 175.49 (14) | C8—C7—C6 | 124.7 (5) |
N1—Mn1—N5 | 93.95 (15) | C11—C7—C6 | 119.1 (5) |
N1—Mn1—N6 | 90.86 (14) | C7—C8—C9 | 120.7 (5) |
N2—Mn1—N3 | 89.86 (13) | C7—C8—H8 | 119.6 |
N2—Mn1—N4 | 94.46 (14) | C9—C8—H8 | 119.6 |
N2—Mn1—N5 | 175.53 (14) | C8—C9—C10 | 119.1 (5) |
N2—Mn1—N6 | 95.16 (14) | C8—C9—H9 | 120.4 |
N3—Mn1—N4 | 84.17 (14) | C10—C9—H9 | 120.4 |
N3—Mn1—N5 | 93.32 (15) | N2—C10—C9 | 121.0 (5) |
N3—Mn1—N6 | 174.40 (14) | N2—C10—H10 | 119.5 |
N4—Mn1—N5 | 88.99 (14) | C9—C10—H10 | 119.5 |
N4—Mn1—N6 | 92.95 (13) | N2—C11—C7 | 124.4 (4) |
N5—Mn1—N6 | 81.81 (15) | N2—C11—C12 | 116.4 (4) |
N6—O1—H1A | 109.5 | C7—C11—C12 | 119.1 (4) |
N5—O2—H2A | 109.5 | N1—C12—C11 | 115.6 (4) |
C25—O3—H3A | 109.5 | N1—C12—C4 | 122.5 (4) |
C26—O4—H4A | 109.5 | C11—C12—C4 | 121.9 (4) |
H11A—O11—H11B | 120 (3) | N3—C13—C14 | 121.0 (5) |
H12A—O12—H12B | 111 (7) | N3—C13—H13 | 119.5 |
C1—N1—C12 | 117.7 (4) | C14—C13—H13 | 119.5 |
C1—N1—Mn1 | 128.8 (3) | C15—C14—C13 | 120.9 (5) |
C12—N1—Mn1 | 113.4 (3) | C15—C14—H14 | 119.6 |
C10—N2—C11 | 118.5 (4) | C13—C14—H14 | 119.6 |
C10—N2—Mn1 | 130.0 (3) | C14—C15—C16 | 119.5 (5) |
C11—N2—Mn1 | 111.6 (3) | C14—C15—H15 | 120.2 |
C13—N3—C24 | 118.0 (4) | C16—C15—H15 | 120.2 |
C13—N3—Mn1 | 130.3 (3) | C24—C16—C15 | 117.5 (4) |
C24—N3—Mn1 | 111.7 (3) | C24—C16—C17 | 117.3 (4) |
C22—N4—C23 | 117.8 (4) | C15—C16—C17 | 125.2 (4) |
C22—N4—Mn1 | 130.0 (3) | C18—C17—C16 | 122.3 (4) |
C23—N4—Mn1 | 112.1 (3) | C18—C17—H17 | 118.8 |
O2—N5—C25 | 122.9 (4) | C16—C17—H17 | 118.8 |
O2—N5—Mn1 | 121.7 (3) | C17—C18—C19 | 121.2 (4) |
C25—N5—Mn1 | 115.4 (3) | C17—C18—H18 | 119.4 |
C26—N6—O1 | 116.4 (3) | C19—C18—H18 | 119.4 |
C26—N6—Mn1 | 116.5 (3) | C23—C19—C20 | 117.0 (4) |
O1—N6—Mn1 | 125.9 (3) | C23—C19—C18 | 117.5 (4) |
O7—N7—O5 | 120.2 (5) | C20—C19—C18 | 125.5 (4) |
O7—N7—O6 | 119.3 (5) | C21—C20—C19 | 119.7 (4) |
O5—N7—O6 | 120.3 (5) | C21—C20—H20 | 120.1 |
O10—N8—O8 | 127.0 (11) | C19—C20—H20 | 120.1 |
O10—N8—O9 | 119.7 (11) | C20—C21—C22 | 120.7 (4) |
O8—N8—O9 | 113.3 (11) | C20—C21—H21 | 119.7 |
N1—C1—C2 | 122.6 (4) | C22—C21—H21 | 119.7 |
N1—C1—H1 | 118.7 | N4—C22—C21 | 121.4 (4) |
C2—C1—H1 | 118.7 | N4—C22—H22 | 119.3 |
C3—C2—C1 | 120.4 (5) | C21—C22—H22 | 119.3 |
C3—C2—H2 | 119.8 | N4—C23—C19 | 123.4 (4) |
C1—C2—H2 | 119.8 | N4—C23—C24 | 115.9 (4) |
C2—C3—C4 | 119.5 (5) | C19—C23—C24 | 120.7 (4) |
C2—C3—H3 | 120.3 | N3—C24—C16 | 123.1 (4) |
C4—C3—H3 | 120.3 | N3—C24—C23 | 116.0 (4) |
C3—C4—C5 | 124.4 (5) | C16—C24—C23 | 120.9 (4) |
C3—C4—C12 | 117.4 (4) | N5—C25—C26 | 112.9 (4) |
C5—C4—C12 | 118.2 (5) | N5—C25—O3 | 121.7 (4) |
C6—C5—C4 | 120.0 (5) | C26—C25—O3 | 125.2 (4) |
C6—C5—H5 | 120.0 | N6—C26—C25 | 113.3 (4) |
C4—C5—H5 | 120.0 | N6—C26—O4 | 123.5 (4) |
C5—C6—C7 | 121.7 (5) | C25—C26—O4 | 123.2 (4) |
C5—C6—H6 | 119.2 |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1A···N2 | 0.82 | 2.67 | 2.991 (4) | 105 |
O2—H2A···O3 | 0.82 | 2.63 | 2.791 (7) | 93 |
C1—H1···N5 | 0.93 | 2.53 | 3.009 (5) | 112 |
C13—H13···N1 | 0.93 | 2.58 | 3.037 (6) | 111 |
C22—H22···N6 | 0.93 | 2.58 | 3.030 (5) | 110 |
O1—H1A···O5i | 0.82 | 2.33 | 2.958 (5) | 134 |
O1—H1A···O6i | 0.82 | 1.96 | 2.674 (5) | 145 |
C3—H3···O5ii | 0.93 | 2.54 | 3.385 (6) | 151 |
C5—H5···O1iii | 0.93 | 2.54 | 3.344 (6) | 145 |
C18—H18···O2iv | 0.93 | 2.37 | 3.225 (6) | 152 |
C22—H22···O6v | 0.93 | 2.52 | 3.269 (6) | 137 |
C15—H15···O5vi | 0.93 | 2.55 | 3.361 (6) | 146 |
Symmetry codes: (i) x, y+1, z−1; (ii) −x+1, −y+1, −z+1; (iii) −x+1, −y+2, −z; (iv) −x+2, −y+1, −z; (v) −x+2, −y+1, −z+1; (vi) x, y, z−1. |
Experimental details
Crystal data | |
Chemical formula | [Mn(C12H8N2)2(C2H4N2O4)](NO3)2·2H2O |
Mr | 695.47 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 273 |
a, b, c (Å) | 13.913 (2), 11.998 (5), 18.131 (3) |
β (°) | 96.228 (4) |
V (Å3) | 3008.6 (14) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.52 |
Crystal size (mm) | 0.30 × 0.23 × 0.18 |
Data collection | |
Diffractometer | Bruker APEX II area-detector |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.861, 0.912 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 20095, 6179, 3132 |
Rint | 0.041 |
(sin θ/λ)max (Å−1) | 0.632 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.051, 0.166, 0.99 |
No. of reflections | 6179 |
No. of parameters | 444 |
No. of restraints | 12 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.65, −0.49 |
Computer programs: APEX2 (Bruker, 2005), SAINT (Siemens, 1996), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Siemens, 1996), SHELXTL.
Mn1—N1 | 1.933 (3) | Mn1—N4 | 1.949 (3) |
Mn1—N2 | 1.966 (3) | Mn1—N5 | 1.881 (4) |
Mn1—N3 | 1.955 (3) | Mn1—N6 | 1.877 (3) |
N1—Mn1—N2 | 82.79 (15) | N2—Mn1—N6 | 95.16 (14) |
N1—Mn1—N3 | 92.23 (14) | N3—Mn1—N4 | 84.17 (14) |
N1—Mn1—N4 | 175.49 (14) | N3—Mn1—N5 | 93.32 (15) |
N1—Mn1—N5 | 93.95 (15) | N3—Mn1—N6 | 174.40 (14) |
N1—Mn1—N6 | 90.86 (14) | N4—Mn1—N5 | 88.99 (14) |
N2—Mn1—N3 | 89.86 (13) | N4—Mn1—N6 | 92.95 (13) |
N2—Mn1—N4 | 94.46 (14) | N5—Mn1—N6 | 81.81 (15) |
N2—Mn1—N5 | 175.53 (14) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1A···N2 | 0.82 | 2.67 | 2.991 (4) | 105 |
O2—H2A···O3 | 0.82 | 2.63 | 2.791 (7) | 93 |
C1—H1···N5 | 0.93 | 2.53 | 3.009 (5) | 112 |
C13—H13···N1 | 0.93 | 2.58 | 3.037 (6) | 111 |
C22—H22···N6 | 0.93 | 2.58 | 3.030 (5) | 110 |
O1—H1A···O5i | 0.82 | 2.33 | 2.958 (5) | 134 |
O1—H1A···O6i | 0.82 | 1.96 | 2.674 (5) | 145 |
C3—H3···O5ii | 0.93 | 2.54 | 3.385 (6) | 151 |
C5—H5···O1iii | 0.93 | 2.54 | 3.344 (6) | 145 |
C18—H18···O2iv | 0.93 | 2.37 | 3.225 (6) | 152 |
C22—H22···O6v | 0.93 | 2.52 | 3.269 (6) | 137 |
C15—H15···O5vi | 0.93 | 2.55 | 3.361 (6) | 146 |
Symmetry codes: (i) x, y+1, z−1; (ii) −x+1, −y+1, −z+1; (iii) −x+1, −y+2, −z; (iv) −x+2, −y+1, −z; (v) −x+2, −y+1, −z+1; (vi) x, y, z−1. |
The crystal structure of bis(1,10-phenanthroline-N,N')(dihydroxy glyoxime) copper(II) dinitrate dihydrate, (II), and bis(1,10-phenanthroline-N,N') (dihydroxy glyoxime) cobalt(II) dinitrate dihydrate, (III), has previously been reported (Liu et al., 2007). The crystal structure determination of the title compound, (I), has been carried out in order to elucidate the molecular conformation and to compare it with that of (II) and (III). We report herein the crystal structure of (I).
In the molecule of (I) (Fig. 1), the ligand bond lengths and angles are within normal ranges (Allen et al., 1987). The six N atoms of one dihydroxy glyoxime and two 1,10-phenanthroline (phen) ligands are coordinated to the Mn atom, in a distorted octahedral arrangement (Table 1). The dihydroxy glyoxime and two phen ligands are each planar and the phen ligands are nearly perpendicular to each other, with a dihedral angle of 86.94 (7)°, as in (II) and (III).
In the crystal structure, the molecules are linked into a three-dimensional framework (Fig. 2) by O—H···O, C—H···O, C—H···N and O—H···N hydrogen bonds (Table 2). There are π-π stacking interactions between adjacent phen ligands with centroid-centroid distance of 3.580 (2) Å (symmetry code: 1 - x, 2 - y, -z). These π-π stacking interactions and hydrogen bonds lead to a supramolecular network structure (Fig. 2), as in (II) and (III). The three compounds, (I), (II) and (III), are isostructural.