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Acta Crystallogr Sect E Struct Rep Online. 2008 May 1; 64(Pt 5): m709.
Published online 2008 April 23. doi:  10.1107/S1600536808010829
PMCID: PMC2961075

Chlorido(chloro­difluoro­acetato-κO)bis(1,10-phenanthroline-κ2 N,N′)manganese(II)

Abstract

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.

Related literature

For isostructural chlorido(1,10-phenanthroline)(trichloro­acetato)manganese(II), see: Chen et al. (2006 [triangle]).

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Object name is e-64-0m709-scheme1.jpg

Experimental

Crystal data

  • [Mn(C2ClF2O2)Cl(C12H8N2)2]
  • M r = 580.27
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-0m709-efi1.jpg
  • a = 16.8822 (4) Å
  • b = 10.3781 (3) Å
  • c = 14.8364 (5) Å
  • β = 108.813 (2)°
  • V = 2460.5 (1) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.80 mm−1
  • T = 100 (2) K
  • 0.20 × 0.15 × 0.10 mm

Data collection

  • Bruker SMART APEXII diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.856, T max = 0.924
  • 30077 measured reflections
  • 5628 independent reflections
  • 3863 reflections with I > 2σ(I)
  • R int = 0.104

Refinement

  • R[F 2 > 2σ(F 2)] = 0.057
  • wR(F 2) = 0.165
  • S = 1.04
  • 5628 reflections
  • 334 parameters
  • H-atom parameters constrained
  • Δρmax = 1.00 e Å−3
  • Δρmin = −0.63 e Å−3

Data collection: APEX2 (Bruker, 2007 [triangle]); cell refinement: SAINT (Bruker, 2007 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: X-SEED (Barbour, 2001 [triangle]); software used to prepare material for publication: publCIF (Westrip, 2008 [triangle]).

Table 1
Selected geometric parameters (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808010829/sg2236sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808010829/sg2236Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

The authors thank the University of Malaya for funding this study (grant No. SF022155/2007A) and also for the purchase of the diffractometer.

supplementary crystallographic information

Comment

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).

Experimental

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.

Refinement

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).

Figures

Fig. 1.
70% Probability thermal ellipsoid plot (Barbour, 2001) of Mn(C12H8N2)2(C2ClF2O2)Cl. Hydrogen atoms are drawn as spheres of arbitrary radii.

Crystal data

[Mn(C2ClF2O2)Cl(C12H8N2)2]F000 = 1172
Mr = 580.27Dx = 1.566 Mg m3
Monoclinic, P21/cMo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 2908 reflections
a = 16.8822 (4) Åθ = 2.3–21.4º
b = 10.3781 (3) ŵ = 0.80 mm1
c = 14.8364 (5) ÅT = 100 (2) K
β = 108.813 (2)ºIrregular block, yellow
V = 2460.5 (1) Å30.20 × 0.15 × 0.10 mm
Z = 4

Data collection

Bruker SMART APEX diffractometer5628 independent reflections
Radiation source: fine-focus sealed tube3863 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.104
T = 100(2) Kθmax = 27.5º
ω scansθmin = 1.3º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)h = −21→21
Tmin = 0.856, Tmax = 0.924k = −13→13
30077 measured reflectionsl = −19→14

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.057H-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 reflectionsΔρmax = 1.00 e Å3
334 parametersΔρmin = −0.62 e Å3
Primary atom site location: structure-invariant direct methodsExtinction correction: none

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
Mn10.28449 (3)0.63507 (5)0.17308 (4)0.02130 (16)
Cl10.33600 (5)0.60920 (8)0.03799 (6)0.0247 (2)
Cl20.21097 (8)1.04489 (11)0.29372 (9)0.0536 (3)
F10.09738 (14)1.0724 (2)0.1347 (2)0.0545 (8)
F20.22337 (14)1.0904 (2)0.13132 (18)0.0402 (6)
O10.24710 (14)0.8334 (2)0.15829 (18)0.0264 (6)
O20.10701 (14)0.8221 (2)0.1178 (2)0.0330 (6)
N10.17254 (16)0.5061 (3)0.1004 (2)0.0240 (6)
N20.21023 (16)0.6109 (3)0.2757 (2)0.0230 (6)
N30.39971 (15)0.7160 (3)0.2897 (2)0.0219 (6)
N40.36197 (16)0.4637 (3)0.2525 (2)0.0215 (6)
C10.1249 (2)0.4714 (3)0.1547 (3)0.0239 (7)
C20.1524 (2)0.4572 (3)0.0131 (3)0.0275 (8)
H20.18570.4800−0.02540.033*
C30.0848 (2)0.3739 (3)−0.0250 (3)0.0338 (9)
H30.07200.3432−0.08850.041*
C40.0376 (2)0.3369 (3)0.0295 (3)0.0312 (9)
H4−0.00800.27930.00490.037*
C50.0572 (2)0.3857 (3)0.1237 (3)0.0279 (8)
C60.0103 (2)0.3542 (3)0.1854 (3)0.0328 (9)
H6−0.03560.29630.16380.039*
C70.0297 (2)0.4050 (4)0.2738 (3)0.0313 (9)
H7−0.00180.38130.31400.038*
C80.0975 (2)0.4944 (3)0.3072 (3)0.0266 (8)
C90.1187 (2)0.5535 (3)0.3974 (3)0.0294 (8)
H90.08850.53320.43970.035*
C100.1829 (2)0.6399 (3)0.4236 (3)0.0316 (8)
H100.19730.68190.48360.038*
C110.2276 (2)0.6658 (3)0.3604 (3)0.0248 (7)
H110.27240.72570.37950.030*
C120.14495 (19)0.5264 (3)0.2484 (3)0.0228 (7)
C130.45711 (19)0.6274 (3)0.3381 (2)0.0217 (7)
C140.4167 (2)0.8390 (3)0.3096 (3)0.0274 (8)
H140.37660.90140.27670.033*
C150.4910 (2)0.8821 (3)0.3767 (3)0.0299 (8)
H150.50060.97160.38910.036*
C160.5496 (2)0.7935 (3)0.4243 (3)0.0282 (8)
H160.60070.82100.46960.034*
C170.5338 (2)0.6622 (3)0.4060 (3)0.0251 (8)
C180.5921 (2)0.5629 (3)0.4517 (3)0.0291 (8)
H180.64460.58610.49620.035*
C190.5738 (2)0.4374 (3)0.4329 (3)0.0280 (8)
H190.61350.37370.46430.034*
C200.4951 (2)0.3985 (3)0.3662 (3)0.0241 (7)
C210.4724 (2)0.2692 (3)0.3466 (3)0.0271 (8)
H210.50970.20250.37780.033*
C220.3961 (2)0.2393 (3)0.2822 (3)0.0284 (8)
H220.37950.15200.26890.034*
C230.3430 (2)0.3395 (3)0.2362 (3)0.0249 (8)
H230.29060.31780.19090.030*
C240.43732 (19)0.4937 (3)0.3181 (2)0.0211 (7)
C250.1748 (2)0.8752 (3)0.1456 (2)0.0234 (7)
C260.1740 (2)1.0211 (3)0.1694 (3)0.0330 (9)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Mn10.0192 (3)0.0265 (3)0.0161 (3)−0.00035 (19)0.0028 (2)−0.0001 (2)
Cl10.0231 (4)0.0310 (4)0.0189 (5)0.0005 (3)0.0053 (3)0.0006 (3)
Cl20.0682 (7)0.0614 (7)0.0398 (7)−0.0225 (6)0.0291 (6)−0.0250 (5)
F10.0351 (12)0.0376 (13)0.086 (2)0.0129 (10)0.0131 (13)0.0026 (13)
F20.0446 (13)0.0359 (12)0.0427 (16)−0.0083 (10)0.0178 (11)0.0021 (11)
O10.0224 (12)0.0323 (13)0.0221 (14)0.0033 (9)0.0038 (10)0.0028 (10)
O20.0236 (12)0.0375 (14)0.0354 (17)−0.0043 (10)0.0061 (12)−0.0090 (12)
N10.0213 (13)0.0294 (15)0.0185 (16)0.0014 (11)0.0024 (12)−0.0009 (12)
N20.0199 (13)0.0282 (15)0.0185 (16)0.0015 (11)0.0028 (12)0.0013 (12)
N30.0200 (13)0.0265 (15)0.0174 (16)−0.0022 (11)0.0036 (12)0.0019 (11)
N40.0207 (13)0.0280 (15)0.0158 (16)−0.0024 (11)0.0057 (12)−0.0013 (11)
C10.0208 (15)0.0279 (17)0.0204 (19)0.0042 (13)0.0032 (14)0.0028 (14)
C20.0279 (17)0.0340 (19)0.017 (2)−0.0003 (14)0.0022 (15)−0.0027 (15)
C30.034 (2)0.037 (2)0.024 (2)−0.0029 (16)0.0000 (17)−0.0069 (16)
C40.0240 (17)0.0299 (19)0.032 (2)−0.0014 (14)−0.0015 (16)−0.0027 (16)
C50.0242 (17)0.0295 (18)0.025 (2)0.0015 (14)0.0017 (15)−0.0007 (15)
C60.0222 (17)0.035 (2)0.037 (2)−0.0039 (14)0.0042 (17)0.0015 (17)
C70.0267 (18)0.037 (2)0.033 (2)0.0002 (15)0.0130 (17)0.0044 (17)
C80.0221 (16)0.0308 (18)0.025 (2)0.0011 (14)0.0044 (15)0.0028 (15)
C90.0291 (18)0.040 (2)0.020 (2)0.0007 (15)0.0101 (16)0.0041 (16)
C100.0336 (19)0.040 (2)0.020 (2)0.0023 (16)0.0070 (16)−0.0016 (16)
C110.0225 (16)0.0343 (18)0.0140 (18)−0.0009 (13)0.0009 (14)−0.0014 (14)
C120.0177 (15)0.0279 (17)0.0197 (19)0.0032 (13)0.0018 (14)0.0015 (14)
C130.0211 (15)0.0271 (17)0.0172 (18)−0.0006 (13)0.0067 (14)0.0018 (14)
C140.0259 (17)0.0265 (18)0.028 (2)−0.0006 (13)0.0063 (16)0.0005 (15)
C150.0263 (17)0.0292 (18)0.030 (2)−0.0073 (14)0.0042 (16)−0.0041 (16)
C160.0240 (16)0.0343 (19)0.024 (2)−0.0074 (14)0.0048 (15)−0.0008 (15)
C170.0229 (16)0.0341 (19)0.0187 (19)−0.0043 (14)0.0071 (15)0.0009 (15)
C180.0202 (16)0.037 (2)0.025 (2)−0.0021 (14)0.0003 (15)−0.0001 (16)
C190.0235 (16)0.0338 (19)0.022 (2)0.0043 (14)0.0014 (15)0.0031 (15)
C200.0209 (16)0.0340 (18)0.0159 (18)0.0020 (14)0.0042 (14)0.0017 (14)
C210.0263 (17)0.0274 (18)0.026 (2)0.0048 (14)0.0061 (15)0.0028 (15)
C220.0268 (17)0.0271 (18)0.028 (2)0.0018 (14)0.0047 (15)0.0000 (15)
C230.0213 (16)0.0295 (18)0.023 (2)−0.0012 (13)0.0055 (15)0.0006 (14)
C240.0206 (15)0.0303 (17)0.0134 (17)0.0002 (13)0.0070 (13)0.0025 (13)
C250.0224 (16)0.0364 (19)0.0107 (17)0.0001 (14)0.0045 (14)0.0008 (14)
C260.0266 (17)0.037 (2)0.035 (2)0.0007 (15)0.0089 (17)−0.0015 (17)

Geometric parameters (Å, °)

Mn1—O12.143 (2)C7—C81.432 (5)
Mn1—N12.283 (3)C7—H70.9500
Mn1—N22.277 (3)C8—C121.401 (5)
Mn1—N32.305 (3)C8—C91.410 (5)
Mn1—N42.295 (3)C9—C101.363 (5)
Mn1—Cl12.443 (1)C9—H90.9500
Cl2—C261.764 (4)C10—C111.405 (5)
F1—C261.339 (4)C10—H100.9500
F2—C261.355 (4)C11—H110.9500
O1—C251.250 (4)C13—C171.407 (5)
O2—C251.217 (4)C13—C241.436 (4)
N1—C21.330 (5)C14—C151.400 (5)
N1—C11.358 (5)C14—H140.9500
N2—C111.324 (5)C15—C161.368 (5)
N2—C121.363 (4)C15—H150.9500
N3—C141.321 (4)C16—C171.398 (5)
N3—C131.361 (4)C16—H160.9500
N4—C231.331 (4)C17—C181.436 (5)
N4—C241.365 (4)C18—C191.346 (5)
C1—C51.403 (5)C18—H180.9500
C1—C121.440 (5)C19—C201.435 (5)
C2—C31.398 (5)C19—H190.9500
C2—H20.9500C20—C211.399 (5)
C3—C41.362 (6)C20—C241.410 (4)
C3—H30.9500C21—C221.369 (5)
C4—C51.422 (5)C21—H210.9500
C4—H40.9500C22—C231.398 (5)
C5—C61.428 (6)C22—H220.9500
C6—C71.353 (6)C23—H230.9500
C6—H60.9500C25—C261.556 (5)
O1—Mn1—N1110.1 (1)C9—C10—C11119.0 (4)
O1—Mn1—N288.1 (1)C9—C10—H10120.5
O1—Mn1—N382.9 (1)C11—C10—H10120.5
O1—Mn1—N4153.8 (1)N2—C11—C10123.3 (3)
O1—Mn1—Cl1101.1 (1)N2—C11—H11118.4
N1—Mn1—N272.6 (1)C10—C11—H11118.3
N1—Mn1—N3159.7 (1)N2—C12—C8122.5 (3)
N1—Mn1—N492.1 (1)N2—C12—C1117.2 (3)
N1—Mn1—Cl190.4 (1)C8—C12—C1120.2 (3)
N2—Mn1—N393.0 (1)N3—C13—C17122.6 (3)
N2—Mn1—N485.2 (1)N3—C13—C24117.8 (3)
N2—Mn1—Cl1162.7 (1)C17—C13—C24119.7 (3)
N3—Mn1—N472.2 (1)N3—C14—C15123.2 (3)
N3—Mn1—Cl1102.6 (1)N3—C14—H14118.4
N4—Mn1—Cl192.4 (1)C15—C14—H14118.4
C25—O1—Mn1126.1 (2)C16—C15—C14119.0 (3)
C2—N1—C1117.6 (3)C16—C15—H15120.5
C2—N1—Mn1126.6 (2)C14—C15—H15120.5
C1—N1—Mn1115.7 (2)C15—C16—C17119.6 (3)
C11—N2—C12117.9 (3)C15—C16—H16120.2
C11—N2—Mn1125.9 (2)C17—C16—H16120.2
C12—N2—Mn1116.0 (2)C16—C17—C13117.6 (3)
C14—N3—C13117.9 (3)C16—C17—C18123.3 (3)
C14—N3—Mn1126.2 (2)C13—C17—C18119.1 (3)
C13—N3—Mn1115.8 (2)C19—C18—C17121.3 (3)
C23—N4—C24117.7 (3)C19—C18—H18119.3
C23—N4—Mn1126.4 (2)C17—C18—H18119.3
C24—N4—Mn1115.8 (2)C18—C19—C20121.0 (3)
N1—C1—C5123.3 (3)C18—C19—H19119.5
N1—C1—C12117.9 (3)C20—C19—H19119.5
C5—C1—C12118.7 (3)C21—C20—C24117.9 (3)
N1—C2—C3123.3 (4)C21—C20—C19123.0 (3)
N1—C2—H2118.4C24—C20—C19119.1 (3)
C3—C2—H2118.4C22—C21—C20119.7 (3)
C4—C3—C2119.5 (4)C22—C21—H21120.2
C4—C3—H3120.3C20—C21—H21120.2
C2—C3—H3120.3C21—C22—C23118.9 (3)
C3—C4—C5119.2 (3)C21—C22—H22120.6
C3—C4—H4120.4C23—C22—H22120.6
C5—C4—H4120.4N4—C23—C22123.5 (3)
C1—C5—C4117.0 (3)N4—C23—H23118.2
C1—C5—C6119.8 (4)C22—C23—H23118.2
C4—C5—C6123.1 (3)N4—C24—C20122.3 (3)
C7—C6—C5121.4 (3)N4—C24—C13117.9 (3)
C7—C6—H6119.3C20—C24—C13119.8 (3)
C5—C6—H6119.3O2—C25—O1131.3 (3)
C6—C7—C8120.3 (4)O2—C25—C26116.1 (3)
C6—C7—H7119.9O1—C25—C26112.5 (3)
C8—C7—H7119.9F1—C26—F2106.1 (3)
C12—C8—C9117.8 (3)F1—C26—C25112.2 (3)
C12—C8—C7119.5 (3)F2—C26—C25111.7 (3)
C9—C8—C7122.7 (3)F1—C26—Cl2108.6 (3)
C10—C9—C8119.5 (4)F2—C26—Cl2107.7 (2)
C10—C9—H9120.3C25—C26—Cl2110.3 (3)
C8—C9—H9120.3
N2—Mn1—O1—C25−45.9 (3)C12—C8—C9—C101.0 (5)
N1—Mn1—O1—C2524.8 (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—C100.9 (5)
Cl1—Mn1—O1—C25119.4 (3)Mn1—N2—C11—C10−175.2 (2)
O1—Mn1—N1—C296.7 (3)C9—C10—C11—N20.4 (5)
N2—Mn1—N1—C2178.0 (3)C11—N2—C12—C8−1.3 (5)
N4—Mn1—N1—C2−97.7 (3)Mn1—N2—C12—C8175.2 (2)
N3—Mn1—N1—C2−135.8 (3)C11—N2—C12—C1177.6 (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—N20.4 (5)
N2—Mn1—N1—C1−5.7 (2)C7—C8—C12—N2179.9 (3)
N4—Mn1—N1—C178.7 (2)C9—C8—C12—C1−178.5 (3)
N3—Mn1—N1—C140.5 (4)C7—C8—C12—C11.0 (5)
Cl1—Mn1—N1—C1171.1 (2)N1—C1—C12—N20.7 (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—C8179.7 (3)
N4—Mn1—N2—C1188.6 (3)C5—C1—C12—C80.0 (5)
N3—Mn1—N2—C1116.7 (3)C14—N3—C13—C17−1.5 (5)
Cl1—Mn1—N2—C11171.2 (2)Mn1—N3—C13—C17174.8 (3)
O1—Mn1—N2—C12117.8 (2)C14—N3—C13—C24178.3 (3)
N1—Mn1—N2—C126.1 (2)Mn1—N3—C13—C24−5.3 (4)
N4—Mn1—N2—C12−87.6 (2)C13—N3—C14—C150.8 (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—C160.3 (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—C130.1 (5)
N1—Mn1—N3—C14−137.4 (3)C15—C16—C17—C18179.2 (4)
N4—Mn1—N3—C14−177.8 (3)N3—C13—C17—C161.1 (5)
Cl1—Mn1—N3—C1493.7 (3)C24—C13—C17—C16−178.8 (3)
O1—Mn1—N3—C13177.9 (2)N3—C13—C17—C18−178.1 (3)
N2—Mn1—N3—C1390.2 (2)C24—C13—C17—C182.1 (5)
N1—Mn1—N3—C1346.6 (4)C16—C17—C18—C19179.0 (4)
N4—Mn1—N3—C136.1 (2)C13—C17—C18—C19−1.9 (6)
Cl1—Mn1—N3—C13−82.3 (2)C17—C18—C19—C200.0 (6)
O1—Mn1—N4—C23159.6 (3)C18—C19—C20—C21−178.0 (4)
N2—Mn1—N4—C2383.7 (3)C18—C19—C20—C241.7 (5)
N1—Mn1—N4—C2311.4 (3)C24—C20—C21—C220.2 (5)
N3—Mn1—N4—C23178.4 (3)C19—C20—C21—C22179.9 (4)
Cl1—Mn1—N4—C23−79.1 (3)C20—C21—C22—C231.0 (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—C22174.8 (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—C201.6 (5)
Cl1—Mn1—N4—C2496.1 (2)Mn1—N4—C24—C20−174.1 (3)
C2—N1—C1—C51.2 (5)C23—N4—C24—C13−178.2 (3)
Mn1—N1—C1—C5−175.5 (2)Mn1—N4—C24—C136.1 (4)
C2—N1—C1—C12−178.5 (3)C21—C20—C24—N4−1.5 (5)
Mn1—N1—C1—C124.8 (4)C19—C20—C24—N4178.8 (3)
C1—N1—C2—C30.7 (5)C21—C20—C24—C13178.3 (3)
Mn1—N1—C2—C3176.9 (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—C51.0 (5)C17—C13—C24—N4179.3 (3)
N1—C1—C5—C4−1.8 (5)N3—C13—C24—C20179.7 (3)
C12—C1—C5—C4177.9 (3)C17—C13—C24—C20−0.5 (5)
N1—C1—C5—C6180.0 (3)Mn1—O1—C25—O2−18.7 (6)
C12—C1—C5—C6−0.3 (5)Mn1—O1—C25—C26161.9 (2)
C3—C4—C5—C10.7 (5)O2—C25—C26—F1−14.5 (5)
C3—C4—C5—C6178.8 (3)O1—C25—C26—F1164.9 (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—F245.9 (4)
C5—C6—C7—C81.2 (5)O2—C25—C26—Cl2106.7 (3)
C6—C7—C8—C12−1.6 (5)O1—C25—C26—Cl2−73.8 (3)
C6—C7—C8—C9177.9 (3)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SG2236).

References

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