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
Key indicators
- Single-crystal X-ray study
- T = 273 K
- Mean (C-C) = 0.007 Å
- R factor = 0.051
- wR factor = 0.166
- Data-to-parameter ratio = 13.9
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT230_ALERT_2_B Hirshfeld Test Diff for O3 - C25 .. 7.46 su PLAT230_ALERT_2_B Hirshfeld Test Diff for O4 - C26 .. 7.31 su PLAT242_ALERT_2_B Check Low Ueq as Compared to Neighbors for C25 PLAT242_ALERT_2_B Check Low Ueq as Compared to Neighbors for C26 PLAT420_ALERT_2_B D-H Without Acceptor O2 - H2A ... ? PLAT420_ALERT_2_B D-H Without Acceptor O3 - H3A ... ? PLAT420_ALERT_2_B D-H Without Acceptor O4 - H4A ... ? PLAT420_ALERT_2_B D-H Without Acceptor O11 - H11B ... ? PLAT420_ALERT_2_B D-H Without Acceptor O12 - H12A ... ? PLAT420_ALERT_2_B D-H Without Acceptor O12 - H12B ... ?
Alert level C PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.97 PLAT214_ALERT_2_C Atom O10 (Anion/Solvent) ADP max/min Ratio 4.40 prola PLAT220_ALERT_2_C Large Non-Solvent O Ueq(max)/Ueq(min) ... 2.56 Ratio PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.76 Ratio PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Mn1 - N1 .. 9.10 su PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Mn1 - N2 .. 5.85 su PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Mn1 - N3 .. 6.74 su PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Mn1 - N4 .. 8.51 su PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Mn1 - N5 .. 6.44 su PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Mn1 - N6 .. 7.74 su PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for O2 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for Mn1 PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for N7 PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for N8 PLAT341_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 7 PLAT480_ALERT_4_C Long H...A H-Bond Reported H1A .. N2 .. 2.67 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H2A .. O3 .. 2.63 Ang. PLAT482_ALERT_4_C Small D-H..A Angle Rep for O2 .. O3 .. 93.00 Deg.
Alert level G PLAT794_ALERT_5_G Check Predicted Bond Valency for Mn1 (4) 4.54 PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 12
0 ALERT level A = In general: serious problem 10 ALERT level B = Potentially serious problem 18 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 20 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 5 ALERT type 4 Improvement, methodology, query or suggestion 1 ALERT type 5 Informative message, check
For a related structure, see: Liu et al. (2007). For bond-length data, see: Allen et al. (1987).
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. |
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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.