Acta Cryst. (2008). E64, m50 [ doi:10.1107/S1600536807063301 ]
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3N1,N2,O]manganese(II)In the title compound, [Mn(C13H11N4O2)2], the Mn atom is coordinated in a distorted octahedral manner by pyridyl N atoms, amidrazonato N atoms and carbamoy O atoms from two tridentate N3-salicyloylpyridine-2-carboxamidrazonato ligands. N-H
O hydrogen bonds result in the formation of two chains, one parallel to the b axis and the other one parallel to the c axis. These two chains are cross-linked, building up layers parallel to the (100) plane.
The ligand N3-salicyloylpyridine-2-carboxamidrazonato (Hspa) was synthesized according to literature (Van Koningsbruggen et al., 1995). [Mn(C13H11N4O2)2] was synthesized by adding ligand (0.0256 g, 0.10 mmol) and Et3N (0.010 g, 0.1 mmol) in 1 ml DMSO to a solution of Mn(acac)2 (0.0253 g, 0.10 mmol) in CH2Cl2 (4 ml). The compound crystallized upon evaporation of the solvent at room temperature after a few days.
H atoms bonded to N and O atoms were located in a difference map and refined with distance restraints, and with Uiso(H) = 1.2Ueq(N,O). Other H atoms were positioned geometrically and refined using a riding model with Uiso(H) = 1.2 times Ueq(C).
Data collection: SMART (Bruker, 2002); cell refinement: SAINT-Plus (Bruker, 2003); data reduction: SAINT-Plus (Bruker, 2003); program(s) used to solve structure: SHELXTL (Bruker, 2000); program(s) used to refine structure: SHELXTL (Bruker, 2000); molecular graphics: ORTEPIII (Burnett & Johnson, 1996), ORTEP-3 for Windows (Farrugia, 1997) and XP (in SHELXTL; Bruker, 2000); software used to prepare material for publication: SHELXTL (Bruker, 2000).
![[Figure 1]](./dn2292fig1thm.gif)
| Fig. 1. A view of the title compound with the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms have been omitted for clarity. |
![[Figure 2]](./dn2292fig2thm.gif)
| Fig. 2. View down a, showing the crosslinking chains by hydrogen bonds. The c axis is horizontal. H atoms not involved in H bondings are removed for purpose of clarity. |
| [Mn(C13H11N4O2)2] | F000 = 1164 |
| Mr = 565.46 | Dx = 1.490 Mg m−3 |
| Monoclinic, P2/c | Mo Kα radiation λ = 0.71073 Å |
| Hall symbol: -P 2yc | Cell parameters from 9514 reflections |
| a = 10.7661 (16) Å | θ = 2.5–28.3º |
| b = 13.049 (2) Å | µ = 0.57 mm−1 |
| c = 19.998 (3) Å | T = 173 (2) K |
| β = 116.192 (7)º | Block, red |
| V = 2521.0 (7) Å3 | 0.35 × 0.32 × 0.28 mm |
| Z = 4 |
| Bruker SMART CCD area-detector diffractometer | 4676 independent reflections |
| Radiation source: fine-focus sealed tube | 4155 reflections with I > 2σ(I) |
| Monochromator: graphite | Rint = 0.051 |
| T = 173(2) K | θmax = 25.5º |
| φ and ω scans | θmin = 1.6º |
| Absorption correction: multi-scan (SADABS; Bruker, 2000) | h = −13→12 |
| Tmin = 0.816, Tmax = 0.850 | k = −15→15 |
| 13210 measured reflections | l = −24→22 |
| 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)] = 0.039 | H-atom parameters constrained |
| wR(F2) = 0.110 | w = 1/[σ2(Fo2) + (0.0484P)2 + 2.5739P] where P = (Fo2 + 2Fc2)/3 |
| S = 1.07 | (Δ/σ)max < 0.001 |
| 4676 reflections | Δρmax = 0.71 e Å−3 |
| 352 parameters | Δρmin = −0.46 e Å−3 |
| Primary atom site location: structure-invariant direct methods | Extinction correction: none |
| [Mn(C13H11N4O2)2] | V = 2521.0 (7) Å3 |
| Mr = 565.46 | Z = 4 |
| Monoclinic, P2/c | Mo Kα |
| a = 10.7661 (16) Å | µ = 0.57 mm−1 |
| b = 13.049 (2) Å | T = 173 (2) K |
| c = 19.998 (3) Å | 0.35 × 0.32 × 0.28 mm |
| β = 116.192 (7)º |
| Bruker SMART CCD area-detector diffractometer | 4676 independent reflections |
| Absorption correction: multi-scan (SADABS; Bruker, 2000) | 4155 reflections with I > 2σ(I) |
| Tmin = 0.816, Tmax = 0.850 | Rint = 0.051 |
| 13210 measured reflections |
| R[F2 > 2σ(F2)] = 0.039 | 352 parameters |
| wR(F2) = 0.110 | H-atom parameters constrained |
| S = 1.07 | Δρmax = 0.71 e Å−3 |
| 4676 reflections | Δρmin = −0.46 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 | 0.48496 (3) | 0.24317 (2) | 0.001305 (18) | 0.01994 (12) | |
| O1 | 0.34073 (16) | 0.27345 (12) | −0.11489 (9) | 0.0227 (3) | |
| O2 | 0.34502 (18) | 0.06726 (13) | −0.27699 (9) | 0.0303 (4) | |
| H2A | 0.4017 | 0.0720 | −0.2318 | 0.045* | |
| O3 | 0.33067 (16) | 0.22300 (12) | 0.04389 (9) | 0.0230 (3) | |
| O4 | 0.33727 (19) | 0.43655 (13) | 0.20316 (10) | 0.0327 (4) | |
| H4A | 0.3958 | 0.4277 | 0.1866 | 0.049* | |
| N1 | 0.64892 (19) | 0.12437 (15) | 0.07874 (10) | 0.0229 (4) | |
| N2 | 0.52421 (19) | 0.13187 (14) | −0.06626 (10) | 0.0210 (4) | |
| N3 | 0.6414 (2) | −0.01103 (14) | −0.08148 (11) | 0.0243 (4) | |
| H3A | 0.6011 | −0.0063 | −0.1304 | 0.029* | |
| H3B | 0.7018 | −0.0602 | −0.0596 | 0.029* | |
| N4 | 0.44572 (19) | 0.13650 (14) | −0.14337 (10) | 0.0218 (4) | |
| N5 | 0.64734 (19) | 0.35892 (15) | −0.00045 (11) | 0.0242 (4) | |
| N6 | 0.6224 (2) | 0.51303 (15) | 0.14364 (11) | 0.0287 (5) | |
| H6A | 0.5814 | 0.5115 | 0.1731 | 0.034* | |
| H6B | 0.6772 | 0.5645 | 0.1462 | 0.034* | |
| N7 | 0.52385 (19) | 0.35738 (14) | 0.08584 (10) | 0.0218 (4) | |
| N8 | 0.4424 (2) | 0.35657 (15) | 0.12401 (11) | 0.0238 (4) | |
| C1 | 0.6845 (2) | 0.05120 (16) | 0.04260 (12) | 0.0194 (4) | |
| C2 | 0.7836 (2) | −0.02275 (18) | 0.08055 (13) | 0.0249 (5) | |
| H2 | 0.8065 | −0.0739 | 0.0540 | 0.030* | |
| C3 | 0.8486 (2) | −0.02049 (19) | 0.15777 (14) | 0.0289 (5) | |
| H3 | 0.9160 | −0.0707 | 0.1849 | 0.035* | |
| C4 | 0.8145 (2) | 0.0552 (2) | 0.19479 (13) | 0.0291 (5) | |
| H4 | 0.8589 | 0.0588 | 0.2477 | 0.035* | |
| C5 | 0.7136 (2) | 0.12593 (19) | 0.15304 (13) | 0.0270 (5) | |
| H5 | 0.6895 | 0.1778 | 0.1786 | 0.032* | |
| C6 | 0.6109 (2) | 0.05651 (16) | −0.04034 (12) | 0.0195 (4) | |
| C7 | 0.3522 (2) | 0.21080 (16) | −0.16168 (12) | 0.0202 (4) | |
| C8 | 0.2524 (2) | 0.21631 (18) | −0.24186 (13) | 0.0228 (5) | |
| C9 | 0.1513 (3) | 0.2926 (2) | −0.26567 (14) | 0.0327 (6) | |
| H9 | 0.1509 | 0.3419 | −0.2308 | 0.039* | |
| C10 | 0.0521 (3) | 0.2982 (2) | −0.33867 (15) | 0.0391 (6) | |
| H10 | −0.0147 | 0.3516 | −0.3538 | 0.047* | |
| C11 | 0.0499 (3) | 0.2261 (2) | −0.38990 (14) | 0.0345 (6) | |
| H11 | −0.0199 | 0.2290 | −0.4399 | 0.041* | |
| C12 | 0.1491 (3) | 0.1499 (2) | −0.36856 (14) | 0.0309 (5) | |
| H12 | 0.1480 | 0.1011 | −0.4041 | 0.037* | |
| C13 | 0.2511 (2) | 0.14416 (17) | −0.29498 (12) | 0.0235 (5) | |
| C14 | 0.6746 (2) | 0.43915 (17) | 0.04641 (12) | 0.0202 (4) | |
| C15 | 0.7624 (2) | 0.51802 (18) | 0.04861 (13) | 0.0264 (5) | |
| H15 | 0.7787 | 0.5742 | 0.0817 | 0.032* | |
| C16 | 0.8263 (3) | 0.51342 (19) | 0.00135 (14) | 0.0297 (5) | |
| H16 | 0.8870 | 0.5665 | 0.0017 | 0.036* | |
| C17 | 0.8001 (3) | 0.4310 (2) | −0.04579 (14) | 0.0319 (6) | |
| H17 | 0.8427 | 0.4259 | −0.0783 | 0.038* | |
| C18 | 0.7105 (3) | 0.3555 (2) | −0.04503 (14) | 0.0306 (5) | |
| H18 | 0.6930 | 0.2986 | −0.0776 | 0.037* | |
| C19 | 0.6018 (2) | 0.43734 (16) | 0.09498 (12) | 0.0208 (5) | |
| C20 | 0.3441 (2) | 0.28614 (17) | 0.09614 (12) | 0.0218 (5) | |
| C21 | 0.2390 (2) | 0.28714 (18) | 0.12565 (12) | 0.0236 (5) | |
| C22 | 0.1321 (3) | 0.21487 (19) | 0.09977 (14) | 0.0285 (5) | |
| H22 | 0.1339 | 0.1612 | 0.0681 | 0.034* | |
| C23 | 0.0237 (3) | 0.2198 (2) | 0.11919 (15) | 0.0348 (6) | |
| H23 | −0.0481 | 0.1701 | 0.1010 | 0.042* | |
| C24 | 0.0211 (3) | 0.2983 (2) | 0.16550 (15) | 0.0389 (6) | |
| H24 | −0.0544 | 0.3033 | 0.1779 | 0.047* | |
| C25 | 0.1270 (3) | 0.3689 (2) | 0.19368 (15) | 0.0361 (6) | |
| H25 | 0.1250 | 0.4212 | 0.2263 | 0.043* | |
| C26 | 0.2376 (3) | 0.36451 (18) | 0.17467 (13) | 0.0267 (5) |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| Mn1 | 0.02221 (19) | 0.01706 (19) | 0.0222 (2) | −0.00067 (13) | 0.01128 (15) | −0.00370 (13) |
| O1 | 0.0249 (8) | 0.0214 (8) | 0.0214 (8) | 0.0025 (6) | 0.0099 (7) | −0.0026 (6) |
| O2 | 0.0325 (9) | 0.0330 (9) | 0.0216 (8) | 0.0076 (7) | 0.0085 (7) | −0.0036 (7) |
| O3 | 0.0269 (8) | 0.0200 (8) | 0.0253 (8) | −0.0025 (6) | 0.0144 (7) | −0.0038 (6) |
| O4 | 0.0392 (10) | 0.0340 (10) | 0.0344 (10) | −0.0081 (8) | 0.0250 (8) | −0.0119 (8) |
| N1 | 0.0224 (9) | 0.0242 (10) | 0.0232 (10) | −0.0024 (8) | 0.0112 (8) | −0.0025 (8) |
| N2 | 0.0223 (9) | 0.0209 (9) | 0.0184 (9) | 0.0006 (8) | 0.0078 (8) | −0.0013 (7) |
| N3 | 0.0295 (10) | 0.0225 (10) | 0.0210 (10) | 0.0074 (8) | 0.0113 (8) | 0.0012 (7) |
| N4 | 0.0224 (9) | 0.0219 (10) | 0.0197 (9) | 0.0015 (8) | 0.0079 (8) | −0.0015 (7) |
| N5 | 0.0248 (10) | 0.0253 (10) | 0.0249 (10) | −0.0018 (8) | 0.0132 (8) | −0.0031 (8) |
| N6 | 0.0400 (12) | 0.0236 (10) | 0.0303 (11) | −0.0106 (9) | 0.0227 (10) | −0.0082 (8) |
| N7 | 0.0241 (9) | 0.0236 (10) | 0.0217 (9) | −0.0030 (8) | 0.0138 (8) | −0.0028 (8) |
| N8 | 0.0273 (10) | 0.0243 (10) | 0.0255 (10) | −0.0026 (8) | 0.0169 (8) | −0.0030 (8) |
| C1 | 0.0187 (10) | 0.0188 (11) | 0.0226 (11) | −0.0041 (8) | 0.0108 (9) | −0.0006 (8) |
| C2 | 0.0239 (11) | 0.0218 (11) | 0.0284 (12) | −0.0010 (9) | 0.0112 (10) | −0.0004 (9) |
| C3 | 0.0248 (12) | 0.0300 (13) | 0.0270 (12) | −0.0007 (10) | 0.0071 (10) | 0.0053 (10) |
| C4 | 0.0263 (12) | 0.0387 (14) | 0.0186 (11) | −0.0060 (10) | 0.0066 (10) | 0.0001 (10) |
| C5 | 0.0282 (12) | 0.0318 (13) | 0.0230 (12) | −0.0036 (10) | 0.0133 (10) | −0.0033 (10) |
| C6 | 0.0185 (10) | 0.0171 (11) | 0.0249 (11) | −0.0041 (8) | 0.0114 (9) | −0.0010 (8) |
| C7 | 0.0227 (11) | 0.0183 (10) | 0.0212 (11) | −0.0014 (9) | 0.0111 (9) | −0.0003 (8) |
| C8 | 0.0229 (11) | 0.0234 (11) | 0.0225 (11) | −0.0004 (9) | 0.0103 (10) | 0.0012 (9) |
| C9 | 0.0323 (13) | 0.0338 (14) | 0.0302 (13) | 0.0082 (11) | 0.0122 (11) | −0.0003 (11) |
| C10 | 0.0320 (14) | 0.0450 (16) | 0.0336 (14) | 0.0164 (12) | 0.0084 (12) | 0.0074 (12) |
| C11 | 0.0276 (13) | 0.0460 (16) | 0.0215 (12) | 0.0006 (11) | 0.0032 (10) | 0.0059 (11) |
| C12 | 0.0313 (13) | 0.0358 (14) | 0.0257 (12) | −0.0037 (11) | 0.0128 (11) | −0.0031 (10) |
| C13 | 0.0249 (11) | 0.0243 (12) | 0.0226 (11) | −0.0023 (9) | 0.0117 (10) | 0.0000 (9) |
| C14 | 0.0170 (10) | 0.0221 (11) | 0.0190 (10) | 0.0017 (8) | 0.0057 (9) | 0.0018 (9) |
| C15 | 0.0236 (12) | 0.0262 (12) | 0.0281 (12) | −0.0028 (9) | 0.0102 (10) | −0.0025 (10) |
| C16 | 0.0226 (11) | 0.0334 (14) | 0.0360 (14) | −0.0040 (10) | 0.0155 (11) | 0.0029 (11) |
| C17 | 0.0291 (13) | 0.0392 (15) | 0.0351 (14) | 0.0000 (11) | 0.0212 (11) | 0.0006 (11) |
| C18 | 0.0324 (13) | 0.0333 (13) | 0.0318 (13) | −0.0012 (10) | 0.0195 (11) | −0.0059 (10) |
| C19 | 0.0207 (11) | 0.0197 (11) | 0.0210 (11) | 0.0017 (8) | 0.0085 (9) | 0.0011 (9) |
| C20 | 0.0266 (11) | 0.0183 (11) | 0.0216 (11) | 0.0008 (9) | 0.0116 (9) | 0.0019 (9) |
| C21 | 0.0274 (12) | 0.0242 (12) | 0.0219 (11) | 0.0004 (9) | 0.0133 (10) | 0.0029 (9) |
| C22 | 0.0322 (13) | 0.0276 (12) | 0.0284 (13) | −0.0035 (10) | 0.0157 (11) | 0.0004 (10) |
| C23 | 0.0302 (13) | 0.0389 (15) | 0.0383 (15) | −0.0085 (11) | 0.0180 (12) | 0.0019 (12) |
| C24 | 0.0351 (14) | 0.0535 (17) | 0.0394 (15) | −0.0013 (13) | 0.0267 (13) | 0.0005 (13) |
| C25 | 0.0392 (15) | 0.0420 (15) | 0.0364 (14) | −0.0009 (12) | 0.0251 (12) | −0.0050 (12) |
| C26 | 0.0313 (12) | 0.0286 (12) | 0.0233 (12) | −0.0005 (10) | 0.0149 (10) | 0.0010 (10) |
| Mn1—N2 | 2.1488 (18) | C4—C5 | 1.389 (3) |
| Mn1—N7 | 2.1517 (18) | C4—H4 | 0.9500 |
| Mn1—O1 | 2.1868 (16) | C5—H5 | 0.9500 |
| Mn1—O3 | 2.1915 (16) | C7—C8 | 1.487 (3) |
| Mn1—N5 | 2.3223 (19) | C8—C9 | 1.394 (3) |
| Mn1—N1 | 2.3461 (19) | C8—C13 | 1.415 (3) |
| O1—C7 | 1.289 (3) | C9—C10 | 1.379 (4) |
| O2—C13 | 1.356 (3) | C9—H9 | 0.9500 |
| O2—H2A | 0.8410 | C10—C11 | 1.384 (4) |
| O3—C20 | 1.288 (3) | C10—H10 | 0.9500 |
| O4—C26 | 1.349 (3) | C11—C12 | 1.382 (4) |
| O4—H4A | 0.8398 | C11—H11 | 0.9500 |
| N1—C5 | 1.334 (3) | C12—C13 | 1.396 (3) |
| N1—C1 | 1.351 (3) | C12—H12 | 0.9500 |
| N2—C6 | 1.296 (3) | C14—C15 | 1.385 (3) |
| N2—N4 | 1.395 (3) | C14—C19 | 1.493 (3) |
| N3—C6 | 1.342 (3) | C15—C16 | 1.394 (3) |
| N3—H3A | 0.8795 | C15—H15 | 0.9500 |
| N3—H3B | 0.8798 | C16—C17 | 1.375 (4) |
| N4—C7 | 1.328 (3) | C16—H16 | 0.9500 |
| N5—C18 | 1.340 (3) | C17—C18 | 1.383 (4) |
| N5—C14 | 1.348 (3) | C17—H17 | 0.9500 |
| N6—C19 | 1.335 (3) | C18—H18 | 0.9500 |
| N6—H6A | 0.8795 | C20—C21 | 1.490 (3) |
| N6—H6B | 0.8797 | C21—C22 | 1.398 (3) |
| N7—C19 | 1.301 (3) | C21—C26 | 1.412 (3) |
| N7—N8 | 1.394 (2) | C22—C23 | 1.384 (4) |
| N8—C20 | 1.324 (3) | C22—H22 | 0.9500 |
| C1—C2 | 1.390 (3) | C23—C24 | 1.389 (4) |
| C1—C6 | 1.491 (3) | C23—H23 | 0.9500 |
| C2—C3 | 1.386 (3) | C24—C25 | 1.379 (4) |
| C2—H2 | 0.9500 | C24—H24 | 0.9500 |
| C3—C4 | 1.377 (4) | C25—C26 | 1.402 (3) |
| C3—H3 | 0.9500 | C25—H25 | 0.9500 |
| N2—Mn1—N7 | 159.74 (7) | N4—C7—C8 | 115.58 (19) |
| N2—Mn1—O1 | 72.45 (6) | C9—C8—C13 | 118.1 (2) |
| N7—Mn1—O1 | 120.69 (7) | C9—C8—C7 | 119.1 (2) |
| N2—Mn1—O3 | 123.80 (7) | C13—C8—C7 | 122.7 (2) |
| N7—Mn1—O3 | 72.29 (6) | C10—C9—C8 | 121.5 (2) |
| O1—Mn1—O3 | 97.47 (6) | C10—C9—H9 | 119.2 |
| N2—Mn1—N5 | 94.12 (7) | C8—C9—H9 | 119.2 |
| N7—Mn1—N5 | 71.01 (7) | C9—C10—C11 | 120.0 (2) |
| O1—Mn1—N5 | 93.02 (6) | C9—C10—H10 | 120.0 |
| O3—Mn1—N5 | 142.07 (6) | C11—C10—H10 | 120.0 |
| N2—Mn1—N1 | 70.67 (7) | C12—C11—C10 | 120.2 (2) |
| N7—Mn1—N1 | 96.34 (7) | C12—C11—H11 | 119.9 |
| O1—Mn1—N1 | 142.69 (6) | C10—C11—H11 | 119.9 |
| O3—Mn1—N1 | 98.21 (6) | C11—C12—C13 | 120.3 (2) |
| N5—Mn1—N1 | 95.03 (7) | C11—C12—H12 | 119.8 |
| C7—O1—Mn1 | 113.97 (14) | C13—C12—H12 | 119.8 |
| C13—O2—H2A | 109.5 | O2—C13—C12 | 117.8 (2) |
| C20—O3—Mn1 | 113.91 (14) | O2—C13—C8 | 122.3 (2) |
| C26—O4—H4A | 109.5 | C12—C13—C8 | 119.9 (2) |
| C5—N1—C1 | 118.4 (2) | N5—C14—C15 | 122.3 (2) |
| C5—N1—Mn1 | 126.56 (16) | N5—C14—C19 | 115.11 (19) |
| C1—N1—Mn1 | 114.98 (14) | C15—C14—C19 | 122.5 (2) |
| C6—N2—N4 | 116.92 (18) | C14—C15—C16 | 118.7 (2) |
| C6—N2—Mn1 | 124.63 (15) | C14—C15—H15 | 120.6 |
| N4—N2—Mn1 | 118.34 (13) | C16—C15—H15 | 120.6 |
| C6—N3—H3A | 120.1 | C17—C16—C15 | 119.0 (2) |
| C6—N3—H3B | 120.0 | C17—C16—H16 | 120.5 |
| H3A—N3—H3B | 119.9 | C15—C16—H16 | 120.5 |
| C7—N4—N2 | 110.61 (17) | C16—C17—C18 | 118.9 (2) |
| C18—N5—C14 | 118.0 (2) | C16—C17—H17 | 120.6 |
| C18—N5—Mn1 | 126.52 (16) | C18—C17—H17 | 120.6 |
| C14—N5—Mn1 | 115.39 (14) | N5—C18—C17 | 123.0 (2) |
| C19—N6—H6A | 120.1 | N5—C18—H18 | 118.5 |
| C19—N6—H6B | 119.9 | C17—C18—H18 | 118.5 |
| H6A—N6—H6B | 120.0 | N7—C19—N6 | 125.8 (2) |
| C19—N7—N8 | 116.90 (18) | N7—C19—C14 | 114.38 (19) |
| C19—N7—Mn1 | 123.76 (14) | N6—C19—C14 | 119.8 (2) |
| N8—N7—Mn1 | 118.28 (13) | O3—C20—N8 | 124.7 (2) |
| C20—N8—N7 | 110.70 (18) | O3—C20—C21 | 119.6 (2) |
| N1—C1—C2 | 122.0 (2) | N8—C20—C21 | 115.63 (19) |
| N1—C1—C6 | 115.17 (19) | C22—C21—C26 | 118.7 (2) |
| C2—C1—C6 | 122.9 (2) | C22—C21—C20 | 119.5 (2) |
| C3—C2—C1 | 118.8 (2) | C26—C21—C20 | 121.6 (2) |
| C3—C2—H2 | 120.6 | C23—C22—C21 | 121.5 (2) |
| C1—C2—H2 | 120.6 | C23—C22—H22 | 119.2 |
| C4—C3—C2 | 119.4 (2) | C21—C22—H22 | 119.2 |
| C4—C3—H3 | 120.3 | C22—C23—C24 | 119.3 (2) |
| C2—C3—H3 | 120.3 | C22—C23—H23 | 120.4 |
| C3—C4—C5 | 118.5 (2) | C24—C23—H23 | 120.4 |
| C3—C4—H4 | 120.8 | C25—C24—C23 | 120.6 (2) |
| C5—C4—H4 | 120.8 | C25—C24—H24 | 119.7 |
| N1—C5—C4 | 123.0 (2) | C23—C24—H24 | 119.7 |
| N1—C5—H5 | 118.5 | C24—C25—C26 | 120.7 (2) |
| C4—C5—H5 | 118.5 | C24—C25—H25 | 119.7 |
| N2—C6—N3 | 125.5 (2) | C26—C25—H25 | 119.7 |
| N2—C6—C1 | 114.53 (19) | O4—C26—C25 | 118.0 (2) |
| N3—C6—C1 | 119.87 (19) | O4—C26—C21 | 122.8 (2) |
| O1—C7—N4 | 124.5 (2) | C25—C26—C21 | 119.2 (2) |
| O1—C7—C8 | 119.82 (19) |
| D—H···A | D—H | H···A | D···A | D—H···A |
| O2—H2A···N4 | 0.84 | 1.82 | 2.564 (2) | 146 |
| O4—H4A···N8 | 0.84 | 1.80 | 2.541 (2) | 147 |
| N3—H3A···O2i | 0.88 | 2.37 | 3.072 (3) | 137 |
| N3—H3B···O3ii | 0.88 | 2.20 | 2.847 (2) | 130 |
| N6—H6A···O4iii | 0.88 | 2.44 | 3.065 (3) | 129 |
| N6—H6B···O1iv | 0.88 | 2.19 | 2.907 (3) | 138 |
| Symmetry codes: (i) −x+1, y, −z−1/2; (ii) −x+1, −y, −z; (iii) −x+1, y, −z+1/2; (iv) −x+1, −y+1, −z. |
| D—H···A | D—H | H···A | D···A | D—H···A |
| O2—H2A···N4 | 0.84 | 1.82 | 2.564 (2) | 146 |
| O4—H4A···N8 | 0.84 | 1.80 | 2.541 (2) | 147 |
| N3—H3A···O2i | 0.88 | 2.37 | 3.072 (3) | 137 |
| N3—H3B···O3ii | 0.88 | 2.20 | 2.847 (2) | 130 |
| N6—H6A···O4iii | 0.88 | 2.44 | 3.065 (3) | 129 |
| N6—H6B···O1iv | 0.88 | 2.19 | 2.907 (3) | 138 |
| Symmetry codes: (i) −x+1, y, −z−1/2; (ii) −x+1, −y, −z; (iii) −x+1, y, −z+1/2; (iv) −x+1, −y+1, −z. |
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Burnett, M. N. & Johnson, C. K. (1996). ORTEPIII. Report ORNL-6895. Oak Ridge National Laboratory, Oak Ridge, Tennessee, USA.
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Van Koningsbruggen, P. J., Haasnoot, J. G., de Graaff, R. A. G. & Reedijk, J. (1995). Inorg. Chim. Acta, 234, 87–94.
Van Koningsbruggen, P. J., Haasnoot, J. G., Graaff, R. A. G. & Reedijk, J. (1993). J. Chem. Soc. Dalton Trans. pp. 483–484.
The N3-salicyloylpyridine-2-carboxamidrazonato ligand (abbreviated as Hspa) has several potential donor atoms and can occur in different chemical and structural conformations. In the Copper(II) coordination compound containing the dehydrogenated spa ligand (Van Koningsbruggen et al., 1995), this spa ligand is fairly planar, whereas in the title complex it is slighted bent around the central Mn—N bonds, with a dihedral angle of 20.53 (7)° between the two aromatic rings (Fig. 1).
Hydrogen bonds N6—H6A···O4 and N3—H3B···O3 forms chain parallel to the b axis (Table 1) whereas hydrogen bonds of N6—H6A···O4 and N3—H3A···O2 result in a chain parallels to c axis. These two chains are crosslinked to build up layers parallel to the (1 0 0) plane. There are also intramolecular O—H···N hydrogen bonds which do not participate to the packing (Table 1).