Acta Cryst. (2008). E64, m500-m501 [ doi:10.1107/S1600536808005230 ]
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2N3,O4)(1,10-phenanthroline-2N,N')manganese(II)The title compound, [Mn(C5H2N2O4)(C12H8N2)(H2O)2], was synthesized by the reaction of manganese(II) acetate and orotic acid in the presence of 1,10-phenanthroline. The crystal structure exhibits intermolecular N-H
O and O-HO hydrogen bonds . The Mn coordination environment consists of an N3O3 donor set in an octahedral geometry.
Orotic acid (0.0012 mol), 1, 10-phenanthroline (0.0012 mol) and Mn(CH3COO)2.2H2O (0.0012 mol, 0.294 g) in 120 ml of water were stirred at 373 K for 24 h; the pH of the solution was adjusted to 6 using a dilute aqueous solution of ammonia. After evaporation of the solution for two weeks, colorless block-like crystals were isolated by filtration. Analysis, calculated for C17H14N4O6Mn: C 48.01, H 3.32, N 13.17; found: C 48.00, H 3.30, N 13.16. Crystals suitable for single-crystal X-ray analysis were selected directly from the sample.
All H atoms were initially located in a difference Fourier map, but placed in idealized positions (C—H 0.93 Å, N—H 0.86 Å), with Uiso(H) = 1.2Ueq(C). The O—H bond lengths were constrained to 0.85Å and the isotropic thermal parameters of the H atoms bonded to water were refined.
Data collection: SMART (Bruker, 2007); cell refinement: SMART (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).
![[Figure 1]](./om2206fig1thm.gif)
| Fig. 1. The structure of the title compound, showing 30% probability displacement ellipsoids and the atom-numbering scheme. The H atoms are omitted. |
| [Mn(C5H2N2O4)(C12H8N2)(H2O)2] | Z = 2 |
| Mr = 425.26 | F000 = 434 |
| Triclinic, P1 | Dx = 1.678 Mg m−3 |
| a = 8.3173 (2) Å | Mo Kα radiation λ = 0.71073 Å |
| b = 8.9875 (2) Å | Cell parameters from 3161 reflections |
| c = 11.9509 (3) Å | θ = 2.4–24.5º |
| α = 78.2780 (10)º | µ = 0.83 mm−1 |
| β = 82.9100 (10)º | T = 293 (2) K |
| γ = 74.7440 (10)º | Block, colorless |
| V = 841.58 (3) Å3 | 0.15 × 0.12 × 0.10 mm |
| Bruker SMART diffractometer | 2950 independent reflections |
| Radiation source: fine-focus sealed tube | 2539 reflections with I > 2σ(I) |
| Monochromator: graphite | Rint = 0.027 |
| T = 293(2) K | θmax = 25.0º |
| φ and ω scans | θmin = 1.8º |
| Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −9→9 |
| Tmin = 0.886, Tmax = 0.922 | k = −10→10 |
| 9718 measured reflections | l = −14→13 |
| Refinement on F2 | Secondary atom site location: difference Fourier map |
| Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
| R[F2 > 2σ(F2)] = 0.030 | H-atom parameters constrained |
| wR(F2) = 0.072 | w = 1/[σ2(Fo2) + (0.0269P)2 + 0.4894P] where P = (Fo2 + 2Fc2)/3 |
| S = 1.05 | (Δ/σ)max = 0.001 |
| 2950 reflections | Δρmax = 0.22 e Å−3 |
| 257 parameters | Δρmin = −0.22 e Å−3 |
| Primary atom site location: structure-invariant direct methods | Extinction correction: none |
| [Mn(C5H2N2O4)(C12H8N2)(H2O)2] | γ = 74.7440 (10)º |
| Mr = 425.26 | V = 841.58 (3) Å3 |
| Triclinic, P1 | Z = 2 |
| a = 8.3173 (2) Å | Mo Kα |
| b = 8.9875 (2) Å | µ = 0.83 mm−1 |
| c = 11.9509 (3) Å | T = 293 (2) K |
| α = 78.2780 (10)º | 0.15 × 0.12 × 0.10 mm |
| β = 82.9100 (10)º |
| Bruker SMART diffractometer | 2950 independent reflections |
| Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 2539 reflections with I > 2σ(I) |
| Tmin = 0.886, Tmax = 0.922 | Rint = 0.027 |
| 9718 measured reflections |
| R[F2 > 2σ(F2)] = 0.030 | 257 parameters |
| wR(F2) = 0.072 | H-atom parameters constrained |
| S = 1.05 | Δρmax = 0.22 e Å−3 |
| 2950 reflections | Δρmin = −0.22 e Å−3 |
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 | 0.11775 (4) | 0.19441 (4) | 0.78756 (3) | 0.03047 (11) | |
| N1 | 0.2989 (2) | −0.03517 (19) | 0.85359 (15) | 0.0276 (4) | |
| N2 | 0.3993 (2) | −0.29802 (19) | 0.93896 (15) | 0.0305 (4) | |
| H2 | 0.3786 | −0.3884 | 0.9636 | 0.037* | |
| N3 | −0.0891 (2) | 0.3718 (2) | 0.68697 (16) | 0.0336 (4) | |
| N4 | 0.1453 (2) | 0.1395 (2) | 0.60556 (16) | 0.0358 (4) | |
| O1 | 0.35761 (18) | 0.24240 (17) | 0.75978 (15) | 0.0416 (4) | |
| O2 | 0.62451 (19) | 0.16456 (19) | 0.79231 (17) | 0.0532 (5) | |
| O3 | 0.13026 (17) | −0.20586 (16) | 0.89654 (13) | 0.0335 (4) | |
| O4 | 0.66615 (18) | −0.40215 (16) | 0.98859 (14) | 0.0385 (4) | |
| O5 | 0.0660 (2) | 0.33271 (19) | 0.92439 (14) | 0.0414 (4) | |
| H5A | 0.1454 | 0.3672 | 0.9392 | 0.085 (11)* | |
| H5B | 0.0168 | 0.3024 | 0.9883 | 0.084 (11)* | |
| O6 | −0.07494 (19) | 0.08117 (19) | 0.86706 (15) | 0.0437 (4) | |
| H6A | −0.1673 | 0.1030 | 0.8365 | 0.071 (10)* | |
| H6B | −0.0474 | −0.0182 | 0.8853 | 0.081 (11)* | |
| C1 | 0.4836 (3) | 0.1428 (2) | 0.79908 (19) | 0.0312 (5) | |
| C2 | 0.4575 (2) | −0.0191 (2) | 0.85488 (17) | 0.0258 (4) | |
| C3 | 0.5858 (3) | −0.1354 (2) | 0.89906 (19) | 0.0304 (5) | |
| H3 | 0.6906 | −0.1167 | 0.8987 | 0.036* | |
| C4 | 0.5589 (3) | −0.2856 (2) | 0.94576 (18) | 0.0294 (5) | |
| C5 | 0.2696 (2) | −0.1773 (2) | 0.89586 (17) | 0.0266 (4) | |
| C6 | −0.2058 (3) | 0.4826 (3) | 0.7282 (2) | 0.0450 (6) | |
| H6 | −0.2016 | 0.4959 | 0.8028 | 0.054* | |
| C7 | −0.3352 (3) | 0.5805 (3) | 0.6641 (3) | 0.0534 (7) | |
| H7 | −0.4157 | 0.6565 | 0.6962 | 0.064* | |
| C8 | −0.3428 (3) | 0.5639 (3) | 0.5547 (3) | 0.0506 (7) | |
| H8 | −0.4273 | 0.6299 | 0.5110 | 0.061* | |
| C9 | −0.2226 (3) | 0.4470 (3) | 0.5079 (2) | 0.0409 (6) | |
| C10 | −0.2204 (3) | 0.4214 (3) | 0.3930 (2) | 0.0508 (7) | |
| H10 | −0.3020 | 0.4849 | 0.3458 | 0.061* | |
| C11 | −0.1026 (4) | 0.3072 (3) | 0.3523 (2) | 0.0518 (7) | |
| H11 | −0.1045 | 0.2926 | 0.2776 | 0.062* | |
| C12 | 0.0259 (3) | 0.2076 (3) | 0.4220 (2) | 0.0427 (6) | |
| C13 | 0.1512 (4) | 0.0871 (3) | 0.3838 (2) | 0.0521 (7) | |
| H13 | 0.1534 | 0.0681 | 0.3099 | 0.062* | |
| C14 | 0.2700 (3) | −0.0023 (3) | 0.4549 (2) | 0.0525 (7) | |
| H14 | 0.3547 | −0.0817 | 0.4300 | 0.063* | |
| C15 | 0.2621 (3) | 0.0277 (3) | 0.5655 (2) | 0.0439 (6) | |
| H15 | 0.3431 | −0.0342 | 0.6138 | 0.053* | |
| C16 | 0.0279 (3) | 0.2301 (3) | 0.53475 (19) | 0.0343 (5) | |
| C17 | −0.0985 (3) | 0.3524 (2) | 0.57867 (19) | 0.0329 (5) |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| Mn1 | 0.02175 (18) | 0.03294 (19) | 0.0356 (2) | −0.00587 (13) | −0.00776 (14) | −0.00124 (14) |
| N1 | 0.0201 (9) | 0.0290 (9) | 0.0327 (10) | −0.0066 (7) | −0.0040 (7) | −0.0010 (7) |
| N2 | 0.0263 (9) | 0.0241 (9) | 0.0415 (11) | −0.0077 (7) | −0.0084 (8) | −0.0008 (8) |
| N3 | 0.0267 (10) | 0.0351 (10) | 0.0387 (11) | −0.0079 (8) | −0.0068 (8) | −0.0029 (8) |
| N4 | 0.0300 (10) | 0.0404 (10) | 0.0362 (11) | −0.0080 (8) | −0.0044 (8) | −0.0048 (9) |
| O1 | 0.0251 (8) | 0.0330 (8) | 0.0610 (11) | −0.0081 (7) | −0.0124 (7) | 0.0117 (7) |
| O2 | 0.0238 (9) | 0.0409 (9) | 0.0900 (14) | −0.0128 (7) | −0.0162 (9) | 0.0134 (9) |
| O3 | 0.0240 (8) | 0.0351 (8) | 0.0431 (9) | −0.0116 (6) | −0.0060 (7) | −0.0026 (7) |
| O4 | 0.0276 (8) | 0.0280 (8) | 0.0585 (11) | −0.0045 (6) | −0.0166 (7) | 0.0006 (7) |
| O5 | 0.0368 (9) | 0.0515 (10) | 0.0428 (10) | −0.0209 (8) | −0.0032 (8) | −0.0105 (8) |
| O6 | 0.0266 (9) | 0.0398 (10) | 0.0637 (12) | −0.0115 (7) | −0.0110 (8) | 0.0022 (8) |
| C1 | 0.0237 (11) | 0.0313 (11) | 0.0374 (13) | −0.0075 (9) | −0.0050 (9) | −0.0011 (9) |
| C2 | 0.0211 (10) | 0.0297 (10) | 0.0268 (11) | −0.0063 (8) | −0.0028 (8) | −0.0046 (8) |
| C3 | 0.0213 (11) | 0.0303 (11) | 0.0401 (13) | −0.0079 (9) | −0.0066 (9) | −0.0031 (9) |
| C4 | 0.0254 (11) | 0.0298 (11) | 0.0338 (12) | −0.0055 (9) | −0.0067 (9) | −0.0069 (9) |
| C5 | 0.0242 (11) | 0.0298 (11) | 0.0265 (11) | −0.0070 (8) | −0.0030 (9) | −0.0052 (9) |
| C6 | 0.0357 (14) | 0.0430 (14) | 0.0547 (16) | −0.0043 (11) | −0.0076 (12) | −0.0096 (12) |
| C7 | 0.0371 (14) | 0.0415 (14) | 0.077 (2) | −0.0003 (11) | −0.0107 (14) | −0.0080 (14) |
| C8 | 0.0368 (14) | 0.0400 (14) | 0.073 (2) | −0.0092 (11) | −0.0255 (13) | 0.0083 (13) |
| C9 | 0.0365 (13) | 0.0380 (13) | 0.0495 (15) | −0.0170 (10) | −0.0175 (11) | 0.0083 (11) |
| C10 | 0.0535 (16) | 0.0579 (16) | 0.0433 (16) | −0.0286 (14) | −0.0259 (13) | 0.0189 (13) |
| C11 | 0.0628 (18) | 0.0657 (18) | 0.0334 (14) | −0.0306 (15) | −0.0145 (13) | 0.0025 (13) |
| C12 | 0.0473 (15) | 0.0529 (15) | 0.0341 (14) | −0.0268 (12) | −0.0046 (11) | −0.0022 (11) |
| C13 | 0.0637 (18) | 0.0646 (17) | 0.0367 (15) | −0.0308 (15) | 0.0069 (13) | −0.0155 (13) |
| C14 | 0.0529 (17) | 0.0530 (16) | 0.0520 (17) | −0.0133 (13) | 0.0118 (14) | −0.0193 (13) |
| C15 | 0.0381 (14) | 0.0452 (14) | 0.0460 (15) | −0.0065 (11) | −0.0009 (11) | −0.0088 (12) |
| C16 | 0.0335 (12) | 0.0402 (12) | 0.0323 (13) | −0.0184 (10) | −0.0046 (10) | 0.0006 (10) |
| C17 | 0.0290 (12) | 0.0359 (12) | 0.0355 (13) | −0.0160 (9) | −0.0076 (10) | 0.0034 (10) |
| Mn1—O1 | 2.1231 (15) | C2—C3 | 1.356 (3) |
| Mn1—O6 | 2.1439 (15) | C3—C4 | 1.416 (3) |
| Mn1—O5 | 2.1852 (16) | C3—H3 | 0.9300 |
| Mn1—N1 | 2.2686 (16) | C6—C7 | 1.396 (3) |
| Mn1—N3 | 2.2880 (18) | C6—H6 | 0.9300 |
| Mn1—N4 | 2.2979 (19) | C7—C8 | 1.356 (4) |
| N1—C5 | 1.348 (3) | C7—H7 | 0.9300 |
| N1—C2 | 1.366 (2) | C8—C9 | 1.401 (4) |
| N2—C4 | 1.375 (3) | C8—H8 | 0.9300 |
| N2—C5 | 1.378 (3) | C9—C17 | 1.402 (3) |
| N2—H2 | 0.8600 | C9—C10 | 1.435 (4) |
| N3—C6 | 1.323 (3) | C10—C11 | 1.344 (4) |
| N3—C17 | 1.355 (3) | C10—H10 | 0.9300 |
| N4—C15 | 1.323 (3) | C11—C12 | 1.432 (4) |
| N4—C16 | 1.356 (3) | C11—H11 | 0.9300 |
| O1—C1 | 1.256 (2) | C12—C13 | 1.399 (4) |
| O2—C1 | 1.229 (2) | C12—C16 | 1.405 (3) |
| O3—C5 | 1.250 (2) | C13—C14 | 1.362 (4) |
| O4—C4 | 1.248 (2) | C13—H13 | 0.9300 |
| O5—H5A | 0.8500 | C14—C15 | 1.392 (4) |
| O5—H5B | 0.8500 | C14—H14 | 0.9300 |
| O6—H6A | 0.8499 | C15—H15 | 0.9300 |
| O6—H6B | 0.8501 | C16—C17 | 1.442 (3) |
| C1—C2 | 1.531 (3) | ||
| O1—Mn1—O6 | 157.87 (6) | O4—C4—N2 | 119.95 (18) |
| O1—Mn1—O5 | 87.31 (6) | O4—C4—C3 | 125.78 (19) |
| O6—Mn1—O5 | 88.81 (6) | N2—C4—C3 | 114.26 (18) |
| O1—Mn1—N1 | 74.55 (6) | O3—C5—N1 | 123.06 (18) |
| O6—Mn1—N1 | 85.75 (6) | O3—C5—N2 | 118.06 (18) |
| O5—Mn1—N1 | 106.65 (6) | N1—C5—N2 | 118.87 (17) |
| O1—Mn1—N3 | 116.16 (6) | N3—C6—C7 | 122.6 (3) |
| O6—Mn1—N3 | 85.65 (6) | N3—C6—H6 | 118.7 |
| O5—Mn1—N3 | 90.50 (6) | C7—C6—H6 | 118.7 |
| N1—Mn1—N3 | 160.61 (6) | C8—C7—C6 | 119.6 (3) |
| O1—Mn1—N4 | 89.63 (7) | C8—C7—H7 | 120.2 |
| O6—Mn1—N4 | 101.40 (7) | C6—C7—H7 | 120.2 |
| O5—Mn1—N4 | 159.04 (7) | C7—C8—C9 | 119.7 (2) |
| N1—Mn1—N4 | 92.45 (6) | C7—C8—H8 | 120.1 |
| N3—Mn1—N4 | 72.31 (7) | C9—C8—H8 | 120.1 |
| C5—N1—C2 | 117.78 (17) | C8—C9—C17 | 117.0 (2) |
| C5—N1—Mn1 | 129.53 (13) | C8—C9—C10 | 123.6 (2) |
| C2—N1—Mn1 | 112.58 (12) | C17—C9—C10 | 119.4 (2) |
| C4—N2—C5 | 125.27 (17) | C11—C10—C9 | 121.2 (2) |
| C4—N2—H2 | 117.4 | C11—C10—H10 | 119.4 |
| C5—N2—H2 | 117.4 | C9—C10—H10 | 119.4 |
| C6—N3—C17 | 118.0 (2) | C10—C11—C12 | 121.0 (2) |
| C6—N3—Mn1 | 125.65 (16) | C10—C11—H11 | 119.5 |
| C17—N3—Mn1 | 116.18 (14) | C12—C11—H11 | 119.5 |
| C15—N4—C16 | 118.1 (2) | C13—C12—C16 | 117.5 (2) |
| C15—N4—Mn1 | 126.10 (16) | C13—C12—C11 | 123.3 (2) |
| C16—N4—Mn1 | 115.76 (15) | C16—C12—C11 | 119.2 (2) |
| C1—O1—Mn1 | 120.96 (13) | C14—C13—C12 | 120.0 (2) |
| Mn1—O5—H5A | 117.0 | C14—C13—H13 | 120.0 |
| Mn1—O5—H5B | 121.2 | C12—C13—H13 | 120.0 |
| H5A—O5—H5B | 106.8 | C13—C14—C15 | 118.7 (2) |
| Mn1—O6—H6A | 119.7 | C13—C14—H14 | 120.6 |
| Mn1—O6—H6B | 117.1 | C15—C14—H14 | 120.6 |
| H6A—O6—H6B | 105.6 | N4—C15—C14 | 123.4 (2) |
| O2—C1—O1 | 124.9 (2) | N4—C15—H15 | 118.3 |
| O2—C1—C2 | 118.71 (18) | C14—C15—H15 | 118.3 |
| O1—C1—C2 | 116.29 (17) | N4—C16—C12 | 122.2 (2) |
| C3—C2—N1 | 124.23 (19) | N4—C16—C17 | 117.9 (2) |
| C3—C2—C1 | 120.98 (18) | C12—C16—C17 | 119.9 (2) |
| N1—C2—C1 | 114.78 (17) | N3—C17—C9 | 123.0 (2) |
| C2—C3—C4 | 119.51 (18) | N3—C17—C16 | 117.71 (19) |
| C2—C3—H3 | 120.2 | C9—C17—C16 | 119.2 (2) |
| C4—C3—H3 | 120.2 | ||
| O1—Mn1—N1—C5 | −176.35 (19) | C5—N2—C4—O4 | 178.6 (2) |
| O6—Mn1—N1—C5 | 13.84 (18) | C5—N2—C4—C3 | −2.7 (3) |
| O5—Mn1—N1—C5 | 101.32 (18) | C2—C3—C4—O4 | 179.8 (2) |
| N3—Mn1—N1—C5 | −50.0 (3) | C2—C3—C4—N2 | 1.1 (3) |
| N4—Mn1—N1—C5 | −87.41 (18) | C2—N1—C5—O3 | −178.39 (19) |
| O1—Mn1—N1—C2 | 7.66 (13) | Mn1—N1—C5—O3 | 5.8 (3) |
| O6—Mn1—N1—C2 | −162.15 (14) | C2—N1—C5—N2 | 0.6 (3) |
| O5—Mn1—N1—C2 | −74.67 (14) | Mn1—N1—C5—N2 | −175.20 (13) |
| N3—Mn1—N1—C2 | 133.99 (19) | C4—N2—C5—O3 | −179.11 (19) |
| N4—Mn1—N1—C2 | 96.60 (14) | C4—N2—C5—N1 | 1.8 (3) |
| O1—Mn1—N3—C6 | −101.28 (19) | C17—N3—C6—C7 | −1.0 (3) |
| O6—Mn1—N3—C6 | 74.74 (19) | Mn1—N3—C6—C7 | −175.60 (18) |
| O5—Mn1—N3—C6 | −14.03 (19) | N3—C6—C7—C8 | −0.6 (4) |
| N1—Mn1—N3—C6 | 138.6 (2) | C6—C7—C8—C9 | 1.2 (4) |
| N4—Mn1—N3—C6 | 178.2 (2) | C7—C8—C9—C17 | −0.3 (3) |
| O1—Mn1—N3—C17 | 84.04 (15) | C7—C8—C9—C10 | −179.7 (2) |
| O6—Mn1—N3—C17 | −99.94 (15) | C8—C9—C10—C11 | −179.8 (2) |
| O5—Mn1—N3—C17 | 171.29 (15) | C17—C9—C10—C11 | 0.7 (4) |
| N1—Mn1—N3—C17 | −36.1 (3) | C9—C10—C11—C12 | −0.4 (4) |
| N4—Mn1—N3—C17 | 3.49 (14) | C10—C11—C12—C13 | 180.0 (2) |
| O1—Mn1—N4—C15 | 60.93 (19) | C10—C11—C12—C16 | 0.1 (4) |
| O6—Mn1—N4—C15 | −99.75 (19) | C16—C12—C13—C14 | −0.5 (4) |
| O5—Mn1—N4—C15 | 142.4 (2) | C11—C12—C13—C14 | 179.6 (2) |
| N1—Mn1—N4—C15 | −13.59 (19) | C12—C13—C14—C15 | 0.8 (4) |
| N3—Mn1—N4—C15 | 178.6 (2) | C16—N4—C15—C14 | −0.4 (3) |
| O1—Mn1—N4—C16 | −120.22 (15) | Mn1—N4—C15—C14 | 178.45 (18) |
| O6—Mn1—N4—C16 | 79.11 (15) | C13—C14—C15—N4 | −0.4 (4) |
| O5—Mn1—N4—C16 | −38.7 (3) | C15—N4—C16—C12 | 0.7 (3) |
| N1—Mn1—N4—C16 | 165.26 (15) | Mn1—N4—C16—C12 | −178.23 (16) |
| N3—Mn1—N4—C16 | −2.52 (14) | C15—N4—C16—C17 | −179.66 (19) |
| O6—Mn1—O1—C1 | 19.9 (3) | Mn1—N4—C16—C17 | 1.4 (2) |
| O5—Mn1—O1—C1 | 100.05 (18) | C13—C12—C16—N4 | −0.3 (3) |
| N1—Mn1—O1—C1 | −8.05 (17) | C11—C12—C16—N4 | 179.6 (2) |
| N3—Mn1—O1—C1 | −170.71 (16) | C13—C12—C16—C17 | −179.9 (2) |
| N4—Mn1—O1—C1 | −100.69 (18) | C11—C12—C16—C17 | 0.0 (3) |
| Mn1—O1—C1—O2 | −175.75 (19) | C6—N3—C17—C9 | 2.0 (3) |
| Mn1—O1—C1—C2 | 6.9 (3) | Mn1—N3—C17—C9 | 177.10 (16) |
| C5—N1—C2—C3 | −2.1 (3) | C6—N3—C17—C16 | −179.21 (19) |
| Mn1—N1—C2—C3 | 174.40 (17) | Mn1—N3—C17—C16 | −4.1 (2) |
| C5—N1—C2—C1 | 176.54 (18) | C8—C9—C17—N3 | −1.4 (3) |
| Mn1—N1—C2—C1 | −7.0 (2) | C10—C9—C17—N3 | 178.1 (2) |
| O2—C1—C2—C3 | 1.8 (3) | C8—C9—C17—C16 | 179.9 (2) |
| O1—C1—C2—C3 | 179.4 (2) | C10—C9—C17—C16 | −0.6 (3) |
| O2—C1—C2—N1 | −176.8 (2) | N4—C16—C17—N3 | 1.8 (3) |
| O1—C1—C2—N1 | 0.7 (3) | C12—C16—C17—N3 | −178.55 (19) |
| N1—C2—C3—C4 | 1.2 (3) | N4—C16—C17—C9 | −179.33 (19) |
| C1—C2—C3—C4 | −177.38 (19) | C12—C16—C17—C9 | 0.3 (3) |
| D—H···A | D—H | H···A | D···A | D—H···A |
| N2—H2···O4i | 0.86 | 1.97 | 2.831 (2) | 177 |
| O5—H5A···O4ii | 0.85 | 2.00 | 2.829 (2) | 164 |
| O5—H5B···O3iii | 0.85 | 1.95 | 2.769 (2) | 162 |
| O6—H6A···O2iv | 0.85 | 1.79 | 2.627 (2) | 170 |
| O6—H6B···O3 | 0.85 | 1.92 | 2.675 (2) | 147 |
| Symmetry codes: (i) −x+1, −y−1, −z+2; (ii) −x+1, −y, −z+2; (iii) −x, −y, −z+2; (iv) x−1, y, z. |
| Mn1—O1 | 2.1231 (15) | Mn1—N1 | 2.2686 (16) |
| Mn1—O6 | 2.1439 (15) | Mn1—N3 | 2.2880 (18) |
| Mn1—O5 | 2.1852 (16) | Mn1—N4 | 2.2979 (19) |
| D—H···A | D—H | H···A | D···A | D—H···A |
| N2—H2···O4i | 0.86 | 1.97 | 2.831 (2) | 177 |
| O5—H5A···O4ii | 0.85 | 2.00 | 2.829 (2) | 164 |
| O5—H5B···O3iii | 0.85 | 1.95 | 2.769 (2) | 162 |
| O6—H6A···O2iv | 0.85 | 1.79 | 2.627 (2) | 170 |
| O6—H6B···O3 | 0.85 | 1.92 | 2.675 (2) | 147 |
| Symmetry codes: (i) −x+1, −y−1, −z+2; (ii) −x+1, −y, −z+2; (iii) −x, −y, −z+2; (iv) x−1, y, z. |
The authors thank the Postgraduate Foundation of Taishan University for financial support.
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Manganese is an important element in organisms and involved in many biochemical processes (Mukhopadhyay et al., 2004 and Ren et al., 2005). It may be observed in the active parts of many enzymes. Orotic acid (2, 6-dioxo-1, 2, 3, 6-tetrahydropyrimidine-4- carboxylic acid), an important pyrimidine derivative as the effective precursor in the biosynthesis of pyrimidine base of nucleic acids in living organisms, plays an important role in bioinorganic chemistry and pharmaceutical studies (Lieberman et al., 1955), material science, coordination chemistry and other aspects (Darensbourg et al., 1998). Many complexes of the orotate ligand have been reported (Hambley et al., 1995).
In the title compound (Fig, 1), Mn(C12H8N2)(C5H2N2O4)(H2O)2, the Mn(II) ion is coordinated by N and O atoms from the orotate (2, 6-dioxo-1, 2, 3, 6-tetrahydropyrimidine- 4-carboxylate) ligand. The bond lengths and angles are in good agreement with reported values (Nepveu et al., 1995). In the crystal structure, the molecule with its two coordinated water molecules is linked into infinite chains by O—H···O and N—H···O hydrogen bonds.