Chlorido(chloro­difluoro­acetato-κO)bis(1,10-phenanthroline-κ2N,N′)manganese(II)

Lo, K.M.; Ng, S.W.

doi:10.1107/S1600536808010829

metal-organic compounds

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ISSN: 2056-9890

Volume 64| Part 5| May 2008| Page m709

doi:10.1107/S1600536808010829

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Chlorido(chlorodifluoroacetato-κO)bis(1,10-phenanthroline-κ²N,N′)manganese(II)

Kong Mun Lo ^a and Seik Weng Ng ^a ^*

^aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 14 April 2008; accepted 18 April 2008; online 23 April 2008)

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 ).

Experimental

Crystal data

[Mn(C₂ClF₂O₂)Cl(C₁₂H₈N₂)₂]
M_r = 580.27
Monoclinic, P 2₁ /c
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 ) 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[F² > 2σ(F²)] = 0.057
wR(F²) = 0.165
S = 1.04
5628 reflections
334 parameters
H-atom parameters constrained
Δρ_max = 1.00 e Å⁻³
Δρ_min = −0.63 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

Mn1—O1	2.143 (2)
Mn1—N1	2.283 (3)
Mn1—N2	2.277 (3)
Mn1—N3	2.305 (3)
Mn1—N4	2.295 (3)
Mn1—Cl1	2.443 (1)

O1—Mn1—N1	110.1 (1)
O1—Mn1—N2	88.1 (1)
O1—Mn1—N3	82.9 (1)
O1—Mn1—N4	153.8 (1)
O1—Mn1—Cl1	101.1 (1)
N1—Mn1—N2	72.6 (1)
N1—Mn1—N3	159.7 (1)
N1—Mn1—N4	92.1 (1)
N1—Mn1—Cl1	90.4 (1)
N2—Mn1—N3	93.0 (1)
N2—Mn1—N4	85.2 (1)
N2—Mn1—Cl1	162.7 (1)
N3—Mn1—N4	72.2 (1)
N3—Mn1—Cl1	102.6 (1)
N4—Mn1—Cl1	92.4 (1)

Data collection: APEX2 (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; 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 ).

Supporting information

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

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

checkCIF report

Comment top

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).

Related literature top

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

Experimental top

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.

Computing details top

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).

Figures top

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

Chlorido(chlorodifluoroacetato-κO)bis(1,10-phenanthroline- κ²N,N')manganese(II) top

Crystal data top

[Mn(C₂ClF₂O₂)Cl(C₁₂H₈N₂)₂]	F(000) = 1172
M_r = 580.27	D_x = 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 = 2.3–21.4°
b = 10.3781 (3) Å	µ = 0.80 mm⁻¹
c = 14.8364 (5) Å	T = 100 K
β = 108.813 (2)°	Irregular block, yellow
V = 2460.5 (1) Å³	0.20 × 0.15 × 0.10 mm
Z = 4

Data collection top

Bruker SMART APEX diffractometer	5628 independent reflections
Radiation source: fine-focus sealed tube	3863 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.104
ω scans	θ_max = 27.5°, θ_min = 1.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −21→21
T_min = 0.856, T_max = 0.924	k = −13→13
30077 measured reflections	l = −19→14

Refinement top

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)] = 0.057	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.165	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0868P)²] where P = (F_o² + 2F_c²)/3
5628 reflections	(Δ/σ)_max = 0.001
334 parameters	Δρ_max = 1.00 e Å⁻³
0 restraints	Δρ_min = −0.63 e Å⁻³

Crystal data top

[Mn(C₂ClF₂O₂)Cl(C₁₂H₈N₂)₂]	V = 2460.5 (1) Å³
M_r = 580.27	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 16.8822 (4) Å	µ = 0.80 mm⁻¹
b = 10.3781 (3) Å	T = 100 K
c = 14.8364 (5) Å	0.20 × 0.15 × 0.10 mm
β = 108.813 (2)°

Data collection top

Bruker SMART APEX diffractometer	5628 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3863 reflections with I > 2σ(I)
T_min = 0.856, T_max = 0.924	R_int = 0.104
30077 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.057	0 restraints
wR(F²) = 0.165	H-atom parameters constrained
S = 1.04	Δρ_max = 1.00 e Å⁻³
5628 reflections	Δρ_min = −0.63 e Å⁻³
334 parameters

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

	x	y	z	U_iso*/U_eq
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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Experimental details

Crystal data
Chemical formula	[Mn(C₂ClF₂O₂)Cl(C₁₂H₈N₂)₂]
M_r	580.27
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	16.8822 (4), 10.3781 (3), 14.8364 (5)
β (°)	108.813 (2)
V (Å³)	2460.5 (1)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.80
Crystal size (mm)	0.20 × 0.15 × 0.10

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.856, 0.924
No. of measured, independent and observed [I > 2σ(I)] reflections	30077, 5628, 3863
R_int	0.104
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.057, 0.165, 1.04
No. of reflections	5628
No. of parameters	334
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.00, −0.63

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2008).

Selected geometric parameters (Å, º) top

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)

Acknowledgements

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

References

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Chen, L., Wang, X.-W., Chen, F.-P., Chen, Y. & Chen, J.-Z. (2006). Acta Cryst. E62, m1743–m1745. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2008). publCIF. In preparation. Google Scholar

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