
Acta Cryst. (2008). E64, m709 [ doi:10.1107/S1600536808010829 ]
O)bis(1,10-phenanthroline-
2N,N')manganese(II)The chloride and chlorodifluoroacetate anions occupy cis positions in the octahedral coordination geometry of the title compound, [Mn(C2ClF2O2)Cl(C12H8N2)2]. The two N-heterocycles both chelate the metal atom.
Manganese dichloride dihydrate (0.5 g, 3 mmol) was dissolved in ethanol and chlorodifluoroacetic acid (0.3 ml, 3 mol) was added. The mixture was heated briefly, after which 1,10-phenanthroline (1.6 g, 6 mmol) was added. The solution when allowed to cool yielded yellow crystals.
Carbon-bound H-atoms were placed in calculated positions (C—H 0.95 Å) and were included in the refinement in the riding model approximation, with U(H) set to 1.2Ueq(C).
Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (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: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2008).
| Fig. 1. 70% Probability thermal ellipsoid plot (Barbour, 2001) of Mn(C12H8N2)2(C2ClF2O2)Cl. Hydrogen atoms are drawn as spheres of arbitrary radii. |
| [Mn(C2ClF2O2)Cl(C12H8N2)2] | F000 = 1172 |
| Mr = 580.27 | Dx = 1.566 Mg m−3 |
| Monoclinic, P21/c | Mo Kα radiation λ = 0.71073 Å |
| Hall symbol: -P 2ybc | Cell parameters from 2908 reflections |
| a = 16.8822 (4) Å | θ = 2.3–21.4º |
| b = 10.3781 (3) Å | µ = 0.80 mm−1 |
| c = 14.8364 (5) Å | T = 100 (2) K |
| β = 108.813 (2)º | Irregular block, yellow |
| V = 2460.5 (1) Å3 | 0.20 × 0.15 × 0.10 mm |
| Z = 4 |
| Bruker SMART APEX diffractometer | 5628 independent reflections |
| Radiation source: fine-focus sealed tube | 3863 reflections with I > 2σ(I) |
| Monochromator: graphite | Rint = 0.104 |
| T = 100(2) K | θmax = 27.5º |
| ω scans | θmin = 1.3º |
| Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −21→21 |
| Tmin = 0.856, Tmax = 0.924 | k = −13→13 |
| 30077 measured reflections | l = −19→14 |
| 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)] = 0.057 | H-atom parameters constrained |
| wR(F2) = 0.165 | w = 1/[σ2(Fo2) + (0.0868P)2] where P = (Fo2 + 2Fc2)/3 |
| S = 1.04 | (Δ/σ)max = 0.001 |
| 5628 reflections | Δρmax = 1.00 e Å−3 |
| 334 parameters | Δρmin = −0.62 e Å−3 |
| Primary atom site location: structure-invariant direct methods | Extinction correction: none |
| [Mn(C2ClF2O2)Cl(C12H8N2)2] | V = 2460.5 (1) Å3 |
| Mr = 580.27 | Z = 4 |
| Monoclinic, P21/c | Mo Kα |
| a = 16.8822 (4) Å | µ = 0.80 mm−1 |
| b = 10.3781 (3) Å | T = 100 (2) K |
| c = 14.8364 (5) Å | 0.20 × 0.15 × 0.10 mm |
| β = 108.813 (2)º |
| Bruker SMART APEX diffractometer | 5628 independent reflections |
| Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 3863 reflections with I > 2σ(I) |
| Tmin = 0.856, Tmax = 0.924 | Rint = 0.104 |
| 30077 measured reflections |
| R[F2 > 2σ(F2)] = 0.057 | 334 parameters |
| wR(F2) = 0.165 | H-atom parameters constrained |
| S = 1.04 | Δρmax = 1.00 e Å−3 |
| 5628 reflections | Δρmin = −0.62 e Å−3 |
| x | y | z | Uiso*/Ueq | ||
| Mn1 | 0.28449 (3) | 0.63507 (5) | 0.17308 (4) | 0.02130 (16) | |
| Cl1 | 0.33600 (5) | 0.60920 (8) | 0.03799 (6) | 0.0247 (2) | |
| Cl2 | 0.21097 (8) | 1.04489 (11) | 0.29372 (9) | 0.0536 (3) | |
| F1 | 0.09738 (14) | 1.0724 (2) | 0.1347 (2) | 0.0545 (8) | |
| F2 | 0.22337 (14) | 1.0904 (2) | 0.13132 (18) | 0.0402 (6) | |
| O1 | 0.24710 (14) | 0.8334 (2) | 0.15829 (18) | 0.0264 (6) | |
| O2 | 0.10701 (14) | 0.8221 (2) | 0.1178 (2) | 0.0330 (6) | |
| N1 | 0.17254 (16) | 0.5061 (3) | 0.1004 (2) | 0.0240 (6) | |
| N2 | 0.21023 (16) | 0.6109 (3) | 0.2757 (2) | 0.0230 (6) | |
| N3 | 0.39971 (15) | 0.7160 (3) | 0.2897 (2) | 0.0219 (6) | |
| N4 | 0.36197 (16) | 0.4637 (3) | 0.2525 (2) | 0.0215 (6) | |
| C1 | 0.1249 (2) | 0.4714 (3) | 0.1547 (3) | 0.0239 (7) | |
| C2 | 0.1524 (2) | 0.4572 (3) | 0.0131 (3) | 0.0275 (8) | |
| H2 | 0.1857 | 0.4800 | −0.0254 | 0.033* | |
| C3 | 0.0848 (2) | 0.3739 (3) | −0.0250 (3) | 0.0338 (9) | |
| H3 | 0.0720 | 0.3432 | −0.0885 | 0.041* | |
| C4 | 0.0376 (2) | 0.3369 (3) | 0.0295 (3) | 0.0312 (9) | |
| H4 | −0.0080 | 0.2793 | 0.0049 | 0.037* | |
| C5 | 0.0572 (2) | 0.3857 (3) | 0.1237 (3) | 0.0279 (8) | |
| C6 | 0.0103 (2) | 0.3542 (3) | 0.1854 (3) | 0.0328 (9) | |
| H6 | −0.0356 | 0.2963 | 0.1638 | 0.039* | |
| C7 | 0.0297 (2) | 0.4050 (4) | 0.2738 (3) | 0.0313 (9) | |
| H7 | −0.0018 | 0.3813 | 0.3140 | 0.038* | |
| C8 | 0.0975 (2) | 0.4944 (3) | 0.3072 (3) | 0.0266 (8) | |
| C9 | 0.1187 (2) | 0.5535 (3) | 0.3974 (3) | 0.0294 (8) | |
| H9 | 0.0885 | 0.5332 | 0.4397 | 0.035* | |
| C10 | 0.1829 (2) | 0.6399 (3) | 0.4236 (3) | 0.0316 (8) | |
| H10 | 0.1973 | 0.6819 | 0.4836 | 0.038* | |
| C11 | 0.2276 (2) | 0.6658 (3) | 0.3604 (3) | 0.0248 (7) | |
| H11 | 0.2724 | 0.7257 | 0.3795 | 0.030* | |
| C12 | 0.14495 (19) | 0.5264 (3) | 0.2484 (3) | 0.0228 (7) | |
| C13 | 0.45711 (19) | 0.6274 (3) | 0.3381 (2) | 0.0217 (7) | |
| C14 | 0.4167 (2) | 0.8390 (3) | 0.3096 (3) | 0.0274 (8) | |
| H14 | 0.3766 | 0.9014 | 0.2767 | 0.033* | |
| C15 | 0.4910 (2) | 0.8821 (3) | 0.3767 (3) | 0.0299 (8) | |
| H15 | 0.5006 | 0.9716 | 0.3891 | 0.036* | |
| C16 | 0.5496 (2) | 0.7935 (3) | 0.4243 (3) | 0.0282 (8) | |
| H16 | 0.6007 | 0.8210 | 0.4696 | 0.034* | |
| C17 | 0.5338 (2) | 0.6622 (3) | 0.4060 (3) | 0.0251 (8) | |
| C18 | 0.5921 (2) | 0.5629 (3) | 0.4517 (3) | 0.0291 (8) | |
| H18 | 0.6446 | 0.5861 | 0.4962 | 0.035* | |
| C19 | 0.5738 (2) | 0.4374 (3) | 0.4329 (3) | 0.0280 (8) | |
| H19 | 0.6135 | 0.3737 | 0.4643 | 0.034* | |
| C20 | 0.4951 (2) | 0.3985 (3) | 0.3662 (3) | 0.0241 (7) | |
| C21 | 0.4724 (2) | 0.2692 (3) | 0.3466 (3) | 0.0271 (8) | |
| H21 | 0.5097 | 0.2025 | 0.3778 | 0.033* | |
| C22 | 0.3961 (2) | 0.2393 (3) | 0.2822 (3) | 0.0284 (8) | |
| H22 | 0.3795 | 0.1520 | 0.2689 | 0.034* | |
| C23 | 0.3430 (2) | 0.3395 (3) | 0.2362 (3) | 0.0249 (8) | |
| H23 | 0.2906 | 0.3178 | 0.1909 | 0.030* | |
| C24 | 0.43732 (19) | 0.4937 (3) | 0.3181 (2) | 0.0211 (7) | |
| C25 | 0.1748 (2) | 0.8752 (3) | 0.1456 (2) | 0.0234 (7) | |
| C26 | 0.1740 (2) | 1.0211 (3) | 0.1694 (3) | 0.0330 (9) |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| Mn1 | 0.0192 (3) | 0.0265 (3) | 0.0161 (3) | −0.00035 (19) | 0.0028 (2) | −0.0001 (2) |
| Cl1 | 0.0231 (4) | 0.0310 (4) | 0.0189 (5) | 0.0005 (3) | 0.0053 (3) | 0.0006 (3) |
| Cl2 | 0.0682 (7) | 0.0614 (7) | 0.0398 (7) | −0.0225 (6) | 0.0291 (6) | −0.0250 (5) |
| F1 | 0.0351 (12) | 0.0376 (13) | 0.086 (2) | 0.0129 (10) | 0.0131 (13) | 0.0026 (13) |
| F2 | 0.0446 (13) | 0.0359 (12) | 0.0427 (16) | −0.0083 (10) | 0.0178 (11) | 0.0021 (11) |
| O1 | 0.0224 (12) | 0.0323 (13) | 0.0221 (14) | 0.0033 (9) | 0.0038 (10) | 0.0028 (10) |
| O2 | 0.0236 (12) | 0.0375 (14) | 0.0354 (17) | −0.0043 (10) | 0.0061 (12) | −0.0090 (12) |
| N1 | 0.0213 (13) | 0.0294 (15) | 0.0185 (16) | 0.0014 (11) | 0.0024 (12) | −0.0009 (12) |
| N2 | 0.0199 (13) | 0.0282 (15) | 0.0185 (16) | 0.0015 (11) | 0.0028 (12) | 0.0013 (12) |
| N3 | 0.0200 (13) | 0.0265 (15) | 0.0174 (16) | −0.0022 (11) | 0.0036 (12) | 0.0019 (11) |
| N4 | 0.0207 (13) | 0.0280 (15) | 0.0158 (16) | −0.0024 (11) | 0.0057 (12) | −0.0013 (11) |
| C1 | 0.0208 (15) | 0.0279 (17) | 0.0204 (19) | 0.0042 (13) | 0.0032 (14) | 0.0028 (14) |
| C2 | 0.0279 (17) | 0.0340 (19) | 0.017 (2) | −0.0003 (14) | 0.0022 (15) | −0.0027 (15) |
| C3 | 0.034 (2) | 0.037 (2) | 0.024 (2) | −0.0029 (16) | 0.0000 (17) | −0.0069 (16) |
| C4 | 0.0240 (17) | 0.0299 (19) | 0.032 (2) | −0.0014 (14) | −0.0015 (16) | −0.0027 (16) |
| C5 | 0.0242 (17) | 0.0295 (18) | 0.025 (2) | 0.0015 (14) | 0.0017 (15) | −0.0007 (15) |
| C6 | 0.0222 (17) | 0.035 (2) | 0.037 (2) | −0.0039 (14) | 0.0042 (17) | 0.0015 (17) |
| C7 | 0.0267 (18) | 0.037 (2) | 0.033 (2) | 0.0002 (15) | 0.0130 (17) | 0.0044 (17) |
| C8 | 0.0221 (16) | 0.0308 (18) | 0.025 (2) | 0.0011 (14) | 0.0044 (15) | 0.0028 (15) |
| C9 | 0.0291 (18) | 0.040 (2) | 0.020 (2) | 0.0007 (15) | 0.0101 (16) | 0.0041 (16) |
| C10 | 0.0336 (19) | 0.040 (2) | 0.020 (2) | 0.0023 (16) | 0.0070 (16) | −0.0016 (16) |
| C11 | 0.0225 (16) | 0.0343 (18) | 0.0140 (18) | −0.0009 (13) | 0.0009 (14) | −0.0014 (14) |
| C12 | 0.0177 (15) | 0.0279 (17) | 0.0197 (19) | 0.0032 (13) | 0.0018 (14) | 0.0015 (14) |
| C13 | 0.0211 (15) | 0.0271 (17) | 0.0172 (18) | −0.0006 (13) | 0.0067 (14) | 0.0018 (14) |
| C14 | 0.0259 (17) | 0.0265 (18) | 0.028 (2) | −0.0006 (13) | 0.0063 (16) | 0.0005 (15) |
| C15 | 0.0263 (17) | 0.0292 (18) | 0.030 (2) | −0.0073 (14) | 0.0042 (16) | −0.0041 (16) |
| C16 | 0.0240 (16) | 0.0343 (19) | 0.024 (2) | −0.0074 (14) | 0.0048 (15) | −0.0008 (15) |
| C17 | 0.0229 (16) | 0.0341 (19) | 0.0187 (19) | −0.0043 (14) | 0.0071 (15) | 0.0009 (15) |
| C18 | 0.0202 (16) | 0.037 (2) | 0.025 (2) | −0.0021 (14) | 0.0003 (15) | −0.0001 (16) |
| C19 | 0.0235 (16) | 0.0338 (19) | 0.022 (2) | 0.0043 (14) | 0.0014 (15) | 0.0031 (15) |
| C20 | 0.0209 (16) | 0.0340 (18) | 0.0159 (18) | 0.0020 (14) | 0.0042 (14) | 0.0017 (14) |
| C21 | 0.0263 (17) | 0.0274 (18) | 0.026 (2) | 0.0048 (14) | 0.0061 (15) | 0.0028 (15) |
| C22 | 0.0268 (17) | 0.0271 (18) | 0.028 (2) | 0.0018 (14) | 0.0047 (15) | 0.0000 (15) |
| C23 | 0.0213 (16) | 0.0295 (18) | 0.023 (2) | −0.0012 (13) | 0.0055 (15) | 0.0006 (14) |
| C24 | 0.0206 (15) | 0.0303 (17) | 0.0134 (17) | 0.0002 (13) | 0.0070 (13) | 0.0025 (13) |
| C25 | 0.0224 (16) | 0.0364 (19) | 0.0107 (17) | 0.0001 (14) | 0.0045 (14) | 0.0008 (14) |
| C26 | 0.0266 (17) | 0.037 (2) | 0.035 (2) | 0.0007 (15) | 0.0089 (17) | −0.0015 (17) |
| Mn1—O1 | 2.143 (2) | C7—C8 | 1.432 (5) |
| Mn1—N1 | 2.283 (3) | C7—H7 | 0.9500 |
| Mn1—N2 | 2.277 (3) | C8—C12 | 1.401 (5) |
| Mn1—N3 | 2.305 (3) | C8—C9 | 1.410 (5) |
| Mn1—N4 | 2.295 (3) | C9—C10 | 1.363 (5) |
| Mn1—Cl1 | 2.443 (1) | C9—H9 | 0.9500 |
| Cl2—C26 | 1.764 (4) | C10—C11 | 1.405 (5) |
| F1—C26 | 1.339 (4) | C10—H10 | 0.9500 |
| F2—C26 | 1.355 (4) | C11—H11 | 0.9500 |
| O1—C25 | 1.250 (4) | C13—C17 | 1.407 (5) |
| O2—C25 | 1.217 (4) | C13—C24 | 1.436 (4) |
| N1—C2 | 1.330 (5) | C14—C15 | 1.400 (5) |
| N1—C1 | 1.358 (5) | C14—H14 | 0.9500 |
| N2—C11 | 1.324 (5) | C15—C16 | 1.368 (5) |
| N2—C12 | 1.363 (4) | C15—H15 | 0.9500 |
| N3—C14 | 1.321 (4) | C16—C17 | 1.398 (5) |
| N3—C13 | 1.361 (4) | C16—H16 | 0.9500 |
| N4—C23 | 1.331 (4) | C17—C18 | 1.436 (5) |
| N4—C24 | 1.365 (4) | C18—C19 | 1.346 (5) |
| C1—C5 | 1.403 (5) | C18—H18 | 0.9500 |
| C1—C12 | 1.440 (5) | C19—C20 | 1.435 (5) |
| C2—C3 | 1.398 (5) | C19—H19 | 0.9500 |
| C2—H2 | 0.9500 | C20—C21 | 1.399 (5) |
| C3—C4 | 1.362 (6) | C20—C24 | 1.410 (4) |
| C3—H3 | 0.9500 | C21—C22 | 1.369 (5) |
| C4—C5 | 1.422 (5) | C21—H21 | 0.9500 |
| C4—H4 | 0.9500 | C22—C23 | 1.398 (5) |
| C5—C6 | 1.428 (6) | C22—H22 | 0.9500 |
| C6—C7 | 1.353 (6) | C23—H23 | 0.9500 |
| C6—H6 | 0.9500 | C25—C26 | 1.556 (5) |
| O1—Mn1—N1 | 110.1 (1) | C9—C10—C11 | 119.0 (4) |
| O1—Mn1—N2 | 88.1 (1) | C9—C10—H10 | 120.5 |
| O1—Mn1—N3 | 82.9 (1) | C11—C10—H10 | 120.5 |
| O1—Mn1—N4 | 153.8 (1) | N2—C11—C10 | 123.3 (3) |
| O1—Mn1—Cl1 | 101.1 (1) | N2—C11—H11 | 118.4 |
| N1—Mn1—N2 | 72.6 (1) | C10—C11—H11 | 118.3 |
| N1—Mn1—N3 | 159.7 (1) | N2—C12—C8 | 122.5 (3) |
| N1—Mn1—N4 | 92.1 (1) | N2—C12—C1 | 117.2 (3) |
| N1—Mn1—Cl1 | 90.4 (1) | C8—C12—C1 | 120.2 (3) |
| N2—Mn1—N3 | 93.0 (1) | N3—C13—C17 | 122.6 (3) |
| N2—Mn1—N4 | 85.2 (1) | N3—C13—C24 | 117.8 (3) |
| N2—Mn1—Cl1 | 162.7 (1) | C17—C13—C24 | 119.7 (3) |
| N3—Mn1—N4 | 72.2 (1) | N3—C14—C15 | 123.2 (3) |
| N3—Mn1—Cl1 | 102.6 (1) | N3—C14—H14 | 118.4 |
| N4—Mn1—Cl1 | 92.4 (1) | C15—C14—H14 | 118.4 |
| C25—O1—Mn1 | 126.1 (2) | C16—C15—C14 | 119.0 (3) |
| C2—N1—C1 | 117.6 (3) | C16—C15—H15 | 120.5 |
| C2—N1—Mn1 | 126.6 (2) | C14—C15—H15 | 120.5 |
| C1—N1—Mn1 | 115.7 (2) | C15—C16—C17 | 119.6 (3) |
| C11—N2—C12 | 117.9 (3) | C15—C16—H16 | 120.2 |
| C11—N2—Mn1 | 125.9 (2) | C17—C16—H16 | 120.2 |
| C12—N2—Mn1 | 116.0 (2) | C16—C17—C13 | 117.6 (3) |
| C14—N3—C13 | 117.9 (3) | C16—C17—C18 | 123.3 (3) |
| C14—N3—Mn1 | 126.2 (2) | C13—C17—C18 | 119.1 (3) |
| C13—N3—Mn1 | 115.8 (2) | C19—C18—C17 | 121.3 (3) |
| C23—N4—C24 | 117.7 (3) | C19—C18—H18 | 119.3 |
| C23—N4—Mn1 | 126.4 (2) | C17—C18—H18 | 119.3 |
| C24—N4—Mn1 | 115.8 (2) | C18—C19—C20 | 121.0 (3) |
| N1—C1—C5 | 123.3 (3) | C18—C19—H19 | 119.5 |
| N1—C1—C12 | 117.9 (3) | C20—C19—H19 | 119.5 |
| C5—C1—C12 | 118.7 (3) | C21—C20—C24 | 117.9 (3) |
| N1—C2—C3 | 123.3 (4) | C21—C20—C19 | 123.0 (3) |
| N1—C2—H2 | 118.4 | C24—C20—C19 | 119.1 (3) |
| C3—C2—H2 | 118.4 | C22—C21—C20 | 119.7 (3) |
| C4—C3—C2 | 119.5 (4) | C22—C21—H21 | 120.2 |
| C4—C3—H3 | 120.3 | C20—C21—H21 | 120.2 |
| C2—C3—H3 | 120.3 | C21—C22—C23 | 118.9 (3) |
| C3—C4—C5 | 119.2 (3) | C21—C22—H22 | 120.6 |
| C3—C4—H4 | 120.4 | C23—C22—H22 | 120.6 |
| C5—C4—H4 | 120.4 | N4—C23—C22 | 123.5 (3) |
| C1—C5—C4 | 117.0 (3) | N4—C23—H23 | 118.2 |
| C1—C5—C6 | 119.8 (4) | C22—C23—H23 | 118.2 |
| C4—C5—C6 | 123.1 (3) | N4—C24—C20 | 122.3 (3) |
| C7—C6—C5 | 121.4 (3) | N4—C24—C13 | 117.9 (3) |
| C7—C6—H6 | 119.3 | C20—C24—C13 | 119.8 (3) |
| C5—C6—H6 | 119.3 | O2—C25—O1 | 131.3 (3) |
| C6—C7—C8 | 120.3 (4) | O2—C25—C26 | 116.1 (3) |
| C6—C7—H7 | 119.9 | O1—C25—C26 | 112.5 (3) |
| C8—C7—H7 | 119.9 | F1—C26—F2 | 106.1 (3) |
| C12—C8—C9 | 117.8 (3) | F1—C26—C25 | 112.2 (3) |
| C12—C8—C7 | 119.5 (3) | F2—C26—C25 | 111.7 (3) |
| C9—C8—C7 | 122.7 (3) | F1—C26—Cl2 | 108.6 (3) |
| C10—C9—C8 | 119.5 (4) | F2—C26—Cl2 | 107.7 (2) |
| C10—C9—H9 | 120.3 | C25—C26—Cl2 | 110.3 (3) |
| C8—C9—H9 | 120.3 | ||
| N2—Mn1—O1—C25 | −45.9 (3) | C12—C8—C9—C10 | 1.0 (5) |
| N1—Mn1—O1—C25 | 24.8 (3) | C7—C8—C9—C10 | −178.5 (3) |
| N4—Mn1—O1—C25 | −121.0 (3) | C8—C9—C10—C11 | −1.4 (5) |
| N3—Mn1—O1—C25 | −139.1 (3) | C12—N2—C11—C10 | 0.9 (5) |
| Cl1—Mn1—O1—C25 | 119.4 (3) | Mn1—N2—C11—C10 | −175.2 (2) |
| O1—Mn1—N1—C2 | 96.7 (3) | C9—C10—C11—N2 | 0.4 (5) |
| N2—Mn1—N1—C2 | 178.0 (3) | C11—N2—C12—C8 | −1.3 (5) |
| N4—Mn1—N1—C2 | −97.7 (3) | Mn1—N2—C12—C8 | 175.2 (2) |
| N3—Mn1—N1—C2 | −135.8 (3) | C11—N2—C12—C1 | 177.6 (3) |
| Cl1—Mn1—N1—C2 | −5.3 (3) | Mn1—N2—C12—C1 | −5.9 (4) |
| O1—Mn1—N1—C1 | −87.0 (2) | C9—C8—C12—N2 | 0.4 (5) |
| N2—Mn1—N1—C1 | −5.7 (2) | C7—C8—C12—N2 | 179.9 (3) |
| N4—Mn1—N1—C1 | 78.7 (2) | C9—C8—C12—C1 | −178.5 (3) |
| N3—Mn1—N1—C1 | 40.5 (4) | C7—C8—C12—C1 | 1.0 (5) |
| Cl1—Mn1—N1—C1 | 171.1 (2) | N1—C1—C12—N2 | 0.7 (4) |
| O1—Mn1—N2—C11 | −66.0 (3) | C5—C1—C12—N2 | −179.0 (3) |
| N1—Mn1—N2—C11 | −177.7 (3) | N1—C1—C12—C8 | 179.7 (3) |
| N4—Mn1—N2—C11 | 88.6 (3) | C5—C1—C12—C8 | 0.0 (5) |
| N3—Mn1—N2—C11 | 16.7 (3) | C14—N3—C13—C17 | −1.5 (5) |
| Cl1—Mn1—N2—C11 | 171.2 (2) | Mn1—N3—C13—C17 | 174.8 (3) |
| O1—Mn1—N2—C12 | 117.8 (2) | C14—N3—C13—C24 | 178.3 (3) |
| N1—Mn1—N2—C12 | 6.1 (2) | Mn1—N3—C13—C24 | −5.3 (4) |
| N4—Mn1—N2—C12 | −87.6 (2) | C13—N3—C14—C15 | 0.8 (5) |
| N3—Mn1—N2—C12 | −159.4 (2) | Mn1—N3—C14—C15 | −175.1 (3) |
| Cl1—Mn1—N2—C12 | −5.0 (4) | N3—C14—C15—C16 | 0.3 (6) |
| O1—Mn1—N3—C14 | −6.1 (3) | C14—C15—C16—C17 | −0.8 (6) |
| N2—Mn1—N3—C14 | −93.8 (3) | C15—C16—C17—C13 | 0.1 (5) |
| N1—Mn1—N3—C14 | −137.4 (3) | C15—C16—C17—C18 | 179.2 (4) |
| N4—Mn1—N3—C14 | −177.8 (3) | N3—C13—C17—C16 | 1.1 (5) |
| Cl1—Mn1—N3—C14 | 93.7 (3) | C24—C13—C17—C16 | −178.8 (3) |
| O1—Mn1—N3—C13 | 177.9 (2) | N3—C13—C17—C18 | −178.1 (3) |
| N2—Mn1—N3—C13 | 90.2 (2) | C24—C13—C17—C18 | 2.1 (5) |
| N1—Mn1—N3—C13 | 46.6 (4) | C16—C17—C18—C19 | 179.0 (4) |
| N4—Mn1—N3—C13 | 6.1 (2) | C13—C17—C18—C19 | −1.9 (6) |
| Cl1—Mn1—N3—C13 | −82.3 (2) | C17—C18—C19—C20 | 0.0 (6) |
| O1—Mn1—N4—C23 | 159.6 (3) | C18—C19—C20—C21 | −178.0 (4) |
| N2—Mn1—N4—C23 | 83.7 (3) | C18—C19—C20—C24 | 1.7 (5) |
| N1—Mn1—N4—C23 | 11.4 (3) | C24—C20—C21—C22 | 0.2 (5) |
| N3—Mn1—N4—C23 | 178.4 (3) | C19—C20—C21—C22 | 179.9 (4) |
| Cl1—Mn1—N4—C23 | −79.1 (3) | C20—C21—C22—C23 | 1.0 (6) |
| O1—Mn1—N4—C24 | −25.2 (4) | C24—N4—C23—C22 | −0.3 (5) |
| N2—Mn1—N4—C24 | −101.0 (2) | Mn1—N4—C23—C22 | 174.8 (3) |
| N1—Mn1—N4—C24 | −173.4 (2) | C21—C22—C23—N4 | −1.0 (6) |
| N3—Mn1—N4—C24 | −6.4 (2) | C23—N4—C24—C20 | 1.6 (5) |
| Cl1—Mn1—N4—C24 | 96.1 (2) | Mn1—N4—C24—C20 | −174.1 (3) |
| C2—N1—C1—C5 | 1.2 (5) | C23—N4—C24—C13 | −178.2 (3) |
| Mn1—N1—C1—C5 | −175.5 (2) | Mn1—N4—C24—C13 | 6.1 (4) |
| C2—N1—C1—C12 | −178.5 (3) | C21—C20—C24—N4 | −1.5 (5) |
| Mn1—N1—C1—C12 | 4.8 (4) | C19—C20—C24—N4 | 178.8 (3) |
| C1—N1—C2—C3 | 0.7 (5) | C21—C20—C24—C13 | 178.3 (3) |
| Mn1—N1—C2—C3 | 176.9 (3) | C19—C20—C24—C13 | −1.4 (5) |
| N1—C2—C3—C4 | −1.8 (5) | N3—C13—C24—N4 | −0.5 (5) |
| C2—C3—C4—C5 | 1.0 (5) | C17—C13—C24—N4 | 179.3 (3) |
| N1—C1—C5—C4 | −1.8 (5) | N3—C13—C24—C20 | 179.7 (3) |
| C12—C1—C5—C4 | 177.9 (3) | C17—C13—C24—C20 | −0.5 (5) |
| N1—C1—C5—C6 | 180.0 (3) | Mn1—O1—C25—O2 | −18.7 (6) |
| C12—C1—C5—C6 | −0.3 (5) | Mn1—O1—C25—C26 | 161.9 (2) |
| C3—C4—C5—C1 | 0.7 (5) | O2—C25—C26—F1 | −14.5 (5) |
| C3—C4—C5—C6 | 178.8 (3) | O1—C25—C26—F1 | 164.9 (3) |
| C1—C5—C6—C7 | −0.2 (5) | O2—C25—C26—F2 | −133.6 (3) |
| C4—C5—C6—C7 | −178.3 (3) | O1—C25—C26—F2 | 45.9 (4) |
| C5—C6—C7—C8 | 1.2 (5) | O2—C25—C26—Cl2 | 106.7 (3) |
| C6—C7—C8—C12 | −1.6 (5) | O1—C25—C26—Cl2 | −73.8 (3) |
| C6—C7—C8—C9 | 177.9 (3) |
| Mn1—O1 | 2.143 (2) | Mn1—N3 | 2.305 (3) |
| Mn1—N1 | 2.283 (3) | Mn1—N4 | 2.295 (3) |
| Mn1—N2 | 2.277 (3) | Mn1—Cl1 | 2.443 (1) |
| O1—Mn1—N1 | 110.1 (1) | N1—Mn1—Cl1 | 90.4 (1) |
| O1—Mn1—N2 | 88.1 (1) | N2—Mn1—N3 | 93.0 (1) |
| O1—Mn1—N3 | 82.9 (1) | N2—Mn1—N4 | 85.2 (1) |
| O1—Mn1—N4 | 153.8 (1) | N2—Mn1—Cl1 | 162.7 (1) |
| O1—Mn1—Cl1 | 101.1 (1) | N3—Mn1—N4 | 72.2 (1) |
| N1—Mn1—N2 | 72.6 (1) | N3—Mn1—Cl1 | 102.6 (1) |
| N1—Mn1—N3 | 159.7 (1) | N4—Mn1—Cl1 | 92.4 (1) |
| N1—Mn1—N4 | 92.1 (1) |
The authors thank the University of Malaya for funding this study (grant No.SF022155/2007 A) and also for the purchase of the diffractometer.
Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191.
Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Chen, L., Wang, X.-W., Chen, F.-P., Chen, Y. & Chen, J.-Z. (2006). Acta Cryst. E62, m1743–m1745.
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.
Westrip, S. P. (2008). publCIF. In preparation.
Manganese dichloride typically reacts with carboxylate anions in the presence of a neutral α,α-dimine ligand (such as 1,10-phenanthroline) to furnish the expected manganese dicarboxylate as the 1:2 adduct of the N-heterocycle. In the case of the reaction with the trichloroacetate anion, only one chloride is displaced. Chlorido-bis(1,10-phenanthroline)(trichloroacetato)manganese exists as a monomeric compound; the crystal structure displays π–π interactions that appear to stabilize the structure (Chen et al., 2006). Replacing the trichloroacetate anion by the chlorodifluoroacetate anion furnishes an isostructural compound (Scheme I, Fig. 1).