Diaqua­hexa-μ2-dichloro­acetato-μ3-oxido-tetra­hydro­furan­diiron(III)manganese(II)

Sadeghi, O.; Amini, M.M.; Ng, S.W.

doi:10.1107/S1600536809054518

metal-organic compounds

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ISSN: 2056-9890

Volume 66| Part 1| January 2010| Page m101

doi:10.1107/S1600536809054518

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Diaquahexa-μ₂-dichloroacetato-μ₃-oxido-tetrahydrofurandiiron(III)manganese(II)

Omid Sadeghi,^a Mostafa M. Amini ^a and Seik Weng Ng ^b ^*

^aDepartment of Chemistry, General Campus, Shahid Beheshti University, Tehran 1983963113, Iran, and ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 17 December 2009; accepted 17 December 2009; online 24 December 2009)

In the oxido-centered title compound, [Fe₂Mn(C₂HCl₂O₂)₆O(C₄H₈O)(H₂O)₂], the central O atom is linked to three metal atoms, which are themselves each linked to four dichloroacetate anions, and is in a triangular configuration. Two of the metal atoms are each coordinated by a water molecule, whereas the third is coordinated by a tetrahydrofuran molecule. In the crystal, adjacent molecules are linked by O—H⋯O and O—H⋯Cl hydrogen bonds across centers of inversion, generating a hydrogen-bonded chain along the c axis. The Mn^II atoms are disordered with respect to the Fe^III atoms, and the same metal site is occupied by 1/3Mn + 2/3Fe.

Related literature

For aquabis(tetrahydrofuran)hexakis(trifluoroacetato)(μ₃-oxido)M(II)diiron(III) (M = copper, zinc), see: Amini et al. (2004a ,b ).

Experimental

Crystal data

[Fe₂Mn(C₂HCl₂O₂)₆O(C₄H₈O)(H₂O)₂]
M_r = 1058.34
Triclinic, $[P \overline 1]$
a = 9.380 (1) Å
b = 13.316 (1) Å
c = 15.432 (1) Å
α = 90.131 (1)°
β = 100.067 (1)°
γ = 97.677 (1)°
V = 1880.1 (2) Å³
Z = 2
Mo Kα radiation
μ = 2.01 mm⁻¹
T = 295 K
0.35 × 0.15 × 0.15 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.540, T_max = 0.753
15425 measured reflections
8543 independent reflections
5788 reflections with I > 2σ(I)
R_int = 0.025

Refinement

R[F² > 2σ(F²)] = 0.063
wR(F²) = 0.207
S = 1.03
8543 reflections
440 parameters
35 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 1.64 e Å⁻³
Δρ_min = −0.90 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1w—H11⋯O3ⁱ	0.85 (1)	2.01 (3)	2.809 (6)	158 (5)
O2w—H22⋯O8ⁱⁱ	0.85 (1)	2.06 (4)	2.821 (5)	149 (7)
O2W—H21⋯O10ⁱⁱ	0.84 (6)	2.19 (7)	2.950 (6)	150 (6)
O1W—H12⋯Cl1ⁱ	0.85 (3)	2.47 (4)	3.288 (4)	160 (6)
Symmetry codes: (i) -x+1, -y+1, -z; (ii) -x+1, -y+1, -z+1.

Data collection: APEX2 (Bruker, 2008 ); cell refinement: SAINT (Bruker, 2008); 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, 2010 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809054518/ci2991sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809054518/ci2991Isup2.hkl

checkCIF report

Related literature top

For aquabis(tetrahydrofuran)hexakis(trifluoroacetato)(µ₃-oxo)metal(II)diiron(III) (metal = copper, zinc), see: Amini et al. (2004a,b).

Experimental top

Sodium bicarbonate (4.12 g, 49 mmol) was dissolved in water (50 ml) and this was mixed with dichloroacetic acid (6.19 g, 48 mmol), ferric nitrate nonahydrate (6.46 g, 16 mmol) dissolved in water (30 ml) along with manganese nitrate hexahydrate (2.36 g, 8 mmol) dissolved in water (5 ml). The mixture was stirred for 24 h. The water was removed under reduced pressure and the residue dissolved in a tetrahydrofuran and hexane mixture. The solvent was removed to give an oily residue. This was treated with hexane to remove the oil; the pure compound was obtained by recrystallization from hexane to which several drops of tetrahydrofuran were added. The brown compound melts at 435–436 K.

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); 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, 2010).

Figures top

Fig. 1. Displacement ellipsoid plot (Barbour, 2001) of Fe₂MnO(H₂O)₂(C₄H₈O)(C₂HO₂Cl₂)₆; ellipsoids are drawn at the 50% probability level and H atoms of arbitrary radius.

Diaquahexa-µ₂-dichloroacetato-µ₃-oxido- tetrahydrofurandiiron(III)manganese(II) top

Crystal data top

[Fe₂Mn(C₂HCl₂O₂)₆O(C₄H₈O)(H₂O)₂]	Z = 2
M_r = 1058.34	F(000) = 1046
Triclinic, P1	D_x = 1.869 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.380 (1) Å	Cell parameters from 4712 reflections
b = 13.316 (1) Å	θ = 2.4–27.4°
c = 15.432 (1) Å	µ = 2.01 mm⁻¹
α = 90.131 (1)°	T = 295 K
β = 100.067 (1)°	Block, brown
γ = 97.677 (1)°	0.35 × 0.15 × 0.15 mm
V = 1880.1 (2) Å³

Data collection top

Bruker SMART APEX diffractometer	8543 independent reflections
Radiation source: fine-focus sealed tube	5788 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.025
ω scans	θ_max = 27.5°, θ_min = 1.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→12
T_min = 0.540, T_max = 0.753	k = −17→17
15425 measured reflections	l = −20→17

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)] = 0.063	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.207	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ²(F_o²) + (0.1141P)² + 3.6071P] where P = (F_o² + 2F_c²)/3
8543 reflections	(Δ/σ)_max = 0.001
440 parameters	Δρ_max = 1.64 e Å⁻³
35 restraints	Δρ_min = −0.90 e Å⁻³

Crystal data top

[Fe₂Mn(C₂HCl₂O₂)₆O(C₄H₈O)(H₂O)₂]	γ = 97.677 (1)°
M_r = 1058.34	V = 1880.1 (2) Å³
Triclinic, P1	Z = 2
a = 9.380 (1) Å	Mo Kα radiation
b = 13.316 (1) Å	µ = 2.01 mm⁻¹
c = 15.432 (1) Å	T = 295 K
α = 90.131 (1)°	0.35 × 0.15 × 0.15 mm
β = 100.067 (1)°

Data collection top

Bruker SMART APEX diffractometer	8543 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	5788 reflections with I > 2σ(I)
T_min = 0.540, T_max = 0.753	R_int = 0.025
15425 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.063	35 restraints
wR(F²) = 0.207	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 1.64 e Å⁻³
8543 reflections	Δρ_min = −0.90 e Å⁻³
440 parameters

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
Fe1	0.48559 (8)	0.58734 (5)	0.15449 (5)	0.02900 (19)	0.67
Fe2	0.70394 (8)	0.77291 (5)	0.26487 (5)	0.03113 (19)	0.67
Fe3	0.62644 (8)	0.55454 (6)	0.36749 (5)	0.0331 (2)	0.67
Mn1	0.48559 (8)	0.58734 (5)	0.15449 (5)	0.02900 (19)	0.33
Mn2	0.70394 (8)	0.77291 (5)	0.26487 (5)	0.03113 (19)	0.33
Mn3	0.62644 (8)	0.55454 (6)	0.36749 (5)	0.0331 (2)	0.33
Cl1	0.7881 (3)	0.31545 (18)	0.11574 (16)	0.0856 (7)
Cl2	0.5060 (4)	0.21726 (17)	0.1440 (3)	0.1210 (11)
Cl3	0.9003 (3)	0.83097 (19)	−0.00937 (16)	0.0953 (8)
Cl4	0.9893 (3)	0.6422 (2)	0.0556 (2)	0.1111 (10)
Cl5	0.3394 (5)	0.9362 (2)	0.0396 (2)	0.1385 (14)
Cl6	0.3033 (4)	0.9569 (2)	0.2189 (3)	0.1291 (12)
Cl7	0.1673 (3)	0.30107 (17)	0.22744 (18)	0.0944 (8)
Cl8	0.0953 (3)	0.4052 (2)	0.37391 (18)	0.1134 (11)
Cl9	0.5161 (3)	0.77820 (18)	0.60071 (13)	0.0888 (7)
Cl10	0.6888 (3)	0.94612 (19)	0.53350 (18)	0.1011 (9)
Cl11	1.2099 (2)	0.7122 (2)	0.3483 (2)	0.1044 (9)
Cl12	1.1217 (3)	0.7937 (2)	0.5016 (2)	0.1191 (11)
O1	0.5657 (5)	0.4523 (3)	0.1497 (3)	0.0473 (10)
O2	0.6456 (5)	0.4239 (3)	0.2908 (3)	0.0490 (10)
O3	0.6341 (4)	0.6367 (3)	0.0718 (3)	0.0449 (9)
O4	0.7827 (5)	0.7618 (3)	0.1493 (3)	0.0522 (11)
O5	0.3761 (4)	0.7103 (3)	0.1277 (3)	0.0485 (10)
O6	0.5320 (4)	0.8361 (3)	0.2003 (3)	0.0532 (11)
O7	0.3171 (4)	0.5173 (3)	0.2051 (3)	0.0503 (10)
O8	0.3900 (4)	0.4967 (3)	0.3482 (2)	0.0421 (9)
O9	0.6494 (6)	0.8139 (3)	0.3790 (3)	0.0556 (11)
O10	0.5825 (4)	0.6753 (3)	0.4504 (3)	0.0426 (9)
O11	0.8568 (4)	0.6037 (3)	0.4047 (3)	0.0487 (10)
O12	0.8968 (4)	0.7428 (3)	0.3279 (3)	0.0523 (11)
O13	0.6045 (4)	0.6424 (2)	0.2557 (2)	0.0310 (7)
O14	0.8102 (5)	0.9224 (3)	0.2647 (3)	0.0485 (10)
O1w	0.3539 (5)	0.5332 (3)	0.0336 (2)	0.0428 (9)
H11	0.354 (9)	0.4734 (18)	0.015 (3)	0.07 (2)*
H12	0.336 (7)	0.570 (3)	−0.011 (2)	0.046 (18)*
O2w	0.6460 (4)	0.4572 (3)	0.4791 (3)	0.0407 (8)
H21	0.580 (7)	0.408 (4)	0.481 (5)	0.08 (3)*
H22	0.662 (11)	0.489 (6)	0.528 (3)	0.13 (4)*
C1	0.6208 (6)	0.4026 (4)	0.2124 (4)	0.0396 (12)
C2	0.6613 (9)	0.2998 (5)	0.1891 (5)	0.0596 (18)
H2	0.7080	0.2706	0.2433	0.072*
C3	0.7428 (6)	0.7024 (4)	0.0862 (3)	0.0364 (11)
C4	0.8391 (7)	0.7079 (6)	0.0146 (5)	0.0615 (19)
H4	0.7829	0.6730	−0.0391	0.074*
C5	0.4141 (6)	0.7987 (4)	0.1553 (4)	0.0425 (13)
C6	0.3003 (8)	0.8696 (5)	0.1314 (7)	0.079 (3)
H6	0.2031	0.8299	0.1170	0.095*
C7	0.3020 (6)	0.4845 (4)	0.2785 (4)	0.0393 (12)
C8	0.1511 (7)	0.4205 (6)	0.2740 (5)	0.0608 (18)
H8	0.0783	0.4525	0.2340	0.073*
C9	0.6017 (6)	0.7685 (4)	0.4403 (4)	0.0374 (11)
C10	0.5580 (7)	0.8389 (5)	0.5070 (4)	0.0504 (15)
H10	0.4682	0.8634	0.4777	0.061*
C11	0.9324 (6)	0.6772 (4)	0.3815 (4)	0.0407 (12)
C12	1.0941 (7)	0.6917 (6)	0.4260 (5)	0.0584 (17)
H12a	1.1148	0.6303	0.4580	0.070*
C13	0.7881 (14)	0.9875 (9)	0.1903 (8)	0.140 (5)
H13A	0.7012	1.0197	0.1900	0.168*
H13B	0.7769	0.9488	0.1356	0.168*
C14	0.9230 (15)	1.0664 (10)	0.2007 (8)	0.143 (5)
H14A	1.0047	1.0406	0.1816	0.171*
H14B	0.9039	1.1280	0.1700	0.171*
C15	0.9457 (18)	1.0811 (8)	0.2983 (8)	0.144 (5)
H15A	0.8773	1.1229	0.3150	0.173*
H15B	1.0445	1.1126	0.3213	0.173*
C16	0.9183 (18)	0.9741 (9)	0.3316 (9)	0.165 (6)
H16A	1.0069	0.9424	0.3396	0.198*
H16B	0.8833	0.9744	0.3871	0.198*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Fe1	0.0335 (4)	0.0263 (4)	0.0262 (4)	0.0008 (3)	0.0051 (3)	0.0000 (3)
Fe2	0.0348 (4)	0.0247 (4)	0.0311 (4)	−0.0016 (3)	0.0025 (3)	0.0006 (3)
Fe3	0.0358 (4)	0.0320 (4)	0.0305 (4)	0.0010 (3)	0.0059 (3)	0.0003 (3)
Mn1	0.0335 (4)	0.0263 (4)	0.0262 (4)	0.0008 (3)	0.0051 (3)	0.0000 (3)
Mn2	0.0348 (4)	0.0247 (4)	0.0311 (4)	−0.0016 (3)	0.0025 (3)	0.0006 (3)
Mn3	0.0358 (4)	0.0320 (4)	0.0305 (4)	0.0010 (3)	0.0059 (3)	0.0003 (3)
Cl1	0.0947 (15)	0.0943 (15)	0.0880 (15)	0.0563 (13)	0.0386 (12)	0.0159 (12)
Cl2	0.131 (2)	0.0474 (11)	0.186 (3)	−0.0117 (13)	0.050 (2)	−0.0354 (15)
Cl3	0.1197 (19)	0.0878 (15)	0.0785 (14)	−0.0301 (14)	0.0511 (14)	0.0132 (12)
Cl4	0.0769 (14)	0.120 (2)	0.155 (3)	0.0284 (14)	0.0592 (17)	−0.0058 (19)
Cl5	0.214 (4)	0.104 (2)	0.098 (2)	0.074 (2)	−0.009 (2)	0.0416 (17)
Cl6	0.134 (2)	0.0947 (19)	0.185 (3)	0.0527 (18)	0.072 (2)	−0.010 (2)
Cl7	0.1038 (17)	0.0655 (13)	0.1057 (18)	−0.0294 (12)	0.0273 (14)	−0.0193 (12)
Cl8	0.0954 (17)	0.150 (3)	0.0903 (17)	−0.0524 (17)	0.0554 (14)	−0.0208 (16)
Cl9	0.145 (2)	0.0797 (14)	0.0520 (11)	0.0171 (14)	0.0442 (12)	−0.0051 (10)
Cl10	0.1105 (18)	0.0784 (14)	0.1083 (18)	−0.0314 (13)	0.0369 (15)	−0.0541 (14)
Cl11	0.0527 (11)	0.142 (2)	0.132 (2)	0.0308 (13)	0.0393 (13)	0.0530 (18)
Cl12	0.0953 (18)	0.121 (2)	0.116 (2)	−0.0117 (16)	−0.0304 (16)	−0.0442 (18)
O1	0.072 (3)	0.033 (2)	0.037 (2)	0.0182 (19)	0.0018 (19)	−0.0010 (16)
O2	0.074 (3)	0.042 (2)	0.034 (2)	0.018 (2)	0.0087 (19)	−0.0006 (17)
O3	0.044 (2)	0.053 (2)	0.035 (2)	−0.0111 (18)	0.0133 (16)	−0.0022 (17)
O4	0.063 (3)	0.046 (2)	0.045 (2)	−0.013 (2)	0.020 (2)	−0.0057 (19)
O5	0.048 (2)	0.038 (2)	0.055 (3)	0.0091 (18)	−0.0061 (19)	0.0007 (18)
O6	0.043 (2)	0.033 (2)	0.075 (3)	0.0012 (17)	−0.010 (2)	0.004 (2)
O7	0.043 (2)	0.065 (3)	0.035 (2)	−0.0156 (19)	0.0043 (17)	0.0022 (19)
O8	0.039 (2)	0.052 (2)	0.033 (2)	−0.0039 (17)	0.0066 (16)	0.0045 (17)
O9	0.088 (3)	0.033 (2)	0.048 (2)	−0.005 (2)	0.028 (2)	−0.0066 (18)
O10	0.055 (2)	0.036 (2)	0.039 (2)	0.0071 (17)	0.0136 (18)	−0.0020 (16)
O11	0.036 (2)	0.049 (2)	0.059 (3)	0.0001 (18)	0.0065 (18)	0.012 (2)
O12	0.039 (2)	0.046 (2)	0.063 (3)	−0.0021 (18)	−0.0071 (19)	0.013 (2)
O13	0.0362 (18)	0.0248 (16)	0.0294 (17)	−0.0007 (13)	0.0021 (14)	0.0022 (13)
O14	0.055 (2)	0.031 (2)	0.054 (3)	−0.0073 (17)	0.003 (2)	0.0038 (17)
O1w	0.051 (2)	0.045 (2)	0.0296 (19)	0.0013 (19)	0.0038 (17)	−0.0049 (17)
O2w	0.046 (2)	0.043 (2)	0.032 (2)	0.0025 (18)	0.0067 (16)	0.0062 (17)
C1	0.049 (3)	0.035 (3)	0.037 (3)	0.007 (2)	0.013 (2)	0.000 (2)
C2	0.101 (5)	0.039 (3)	0.048 (4)	0.032 (3)	0.020 (4)	0.004 (3)
C3	0.040 (3)	0.038 (3)	0.032 (3)	0.001 (2)	0.011 (2)	0.002 (2)
C4	0.052 (4)	0.080 (5)	0.052 (4)	−0.019 (3)	0.027 (3)	−0.009 (3)
C5	0.036 (3)	0.039 (3)	0.051 (3)	0.004 (2)	0.005 (2)	0.009 (3)
C6	0.046 (4)	0.038 (3)	0.145 (8)	0.011 (3)	−0.010 (4)	0.016 (4)
C7	0.030 (2)	0.044 (3)	0.042 (3)	−0.005 (2)	0.008 (2)	−0.005 (2)
C8	0.047 (3)	0.067 (4)	0.065 (4)	−0.015 (3)	0.016 (3)	0.000 (3)
C9	0.040 (3)	0.034 (3)	0.036 (3)	0.002 (2)	0.001 (2)	−0.005 (2)
C10	0.060 (4)	0.045 (3)	0.047 (3)	0.006 (3)	0.013 (3)	−0.012 (3)
C11	0.033 (3)	0.043 (3)	0.045 (3)	0.006 (2)	0.004 (2)	−0.004 (2)
C12	0.038 (3)	0.063 (4)	0.069 (4)	0.002 (3)	−0.002 (3)	0.012 (3)
C13	0.154 (9)	0.108 (7)	0.138 (8)	−0.014 (7)	−0.003 (7)	0.030 (7)
C14	0.152 (8)	0.112 (7)	0.154 (9)	−0.030 (6)	0.039 (7)	0.032 (7)
C15	0.188 (9)	0.082 (6)	0.136 (8)	−0.059 (6)	0.013 (7)	0.009 (6)
C16	0.179 (9)	0.122 (8)	0.167 (9)	−0.020 (7)	−0.010 (8)	0.010 (7)

Geometric parameters (Å, º) top

Fe1—O13	1.841 (3)	O7—C7	1.239 (7)
Fe1—O7	2.004 (4)	O8—C7	1.232 (7)
Fe1—O1	2.045 (4)	O9—C9	1.241 (7)
Fe1—O5	2.052 (4)	O10—C9	1.244 (6)
Fe1—O3	2.092 (4)	O11—C11	1.222 (7)
Fe1—O1w	2.116 (4)	O12—C11	1.241 (7)
Fe2—O13	1.852 (3)	O14—C16	1.419 (9)
Fe2—O12	1.991 (4)	O14—C13	1.442 (8)
Fe2—O9	2.012 (4)	O1w—H11	0.85 (1)
Fe2—O6	2.026 (4)	O1w—H12	0.85 (1)
Fe2—O4	2.058 (4)	O2w—H21	0.85 (1)
Fe2—O14	2.104 (4)	O2w—H22	0.85 (1)
Fe3—O13	2.082 (3)	C1—C2	1.528 (8)
Fe3—O2	2.146 (4)	C2—H2	0.98
Fe3—O11	2.148 (4)	C3—C4	1.541 (8)
Fe3—O2w	2.155 (4)	C4—H4	0.98
Fe3—O10	2.178 (4)	C5—C6	1.516 (8)
Fe3—O8	2.216 (4)	C6—H6	0.98
Cl1—C2	1.773 (8)	C7—C8	1.542 (8)
Cl2—C2	1.740 (9)	C8—H8	0.98
Cl3—C4	1.725 (8)	C9—C10	1.534 (8)
Cl4—C4	1.781 (9)	C10—H10	0.98
Cl5—C6	1.740 (10)	C11—C12	1.538 (8)
Cl6—C6	1.774 (10)	C12—H12a	0.98
Cl7—C8	1.779 (8)	C13—C14	1.519 (9)
Cl8—C8	1.717 (7)	C13—H13A	0.97
Cl9—C10	1.736 (7)	C13—H13B	0.97
Cl10—C10	1.751 (7)	C14—C15	1.493 (9)
Cl11—C12	1.751 (8)	C14—H14A	0.97
Cl12—C12	1.752 (8)	C14—H14B	0.97
O1—C1	1.250 (7)	C15—C16	1.521 (9)
O2—C1	1.217 (7)	C15—H15A	0.97
O3—C3	1.240 (6)	C15—H15B	0.97
O4—C3	1.226 (7)	C16—H16A	0.97
O5—C5	1.236 (7)	C16—H16B	0.97
O6—C5	1.240 (7)

O13—Fe1—O7	100.17 (16)	Cl2—C2—Cl1	111.0 (4)
O13—Fe1—O1	98.93 (16)	C1—C2—H2	108.3
O7—Fe1—O1	89.64 (19)	Cl2—C2—H2	108.3
O13—Fe1—O5	95.75 (16)	Cl1—C2—H2	108.3
O7—Fe1—O5	89.80 (19)	O4—C3—O3	128.6 (5)
O1—Fe1—O5	165.17 (16)	O4—C3—C4	117.0 (5)
O13—Fe1—O3	94.81 (15)	O3—C3—C4	114.4 (5)
O7—Fe1—O3	164.61 (16)	C3—C4—Cl3	112.5 (5)
O1—Fe1—O3	84.53 (18)	C3—C4—Cl4	106.3 (5)
O5—Fe1—O3	92.22 (18)	Cl3—C4—Cl4	110.5 (4)
O13—Fe1—O1w	176.02 (16)	C3—C4—H4	109.1
O7—Fe1—O1w	83.07 (16)	Cl3—C4—H4	109.1
O1—Fe1—O1w	83.33 (17)	Cl4—C4—H4	109.1
O5—Fe1—O1w	81.89 (17)	O5—C5—O6	128.3 (5)
O3—Fe1—O1w	82.11 (16)	O5—C5—C6	115.3 (5)
O13—Fe2—O12	98.58 (16)	O6—C5—C6	116.4 (6)
O13—Fe2—O9	97.57 (16)	C5—C6—Cl5	107.9 (6)
O12—Fe2—O9	90.9 (2)	C5—C6—Cl6	111.4 (6)
O13—Fe2—O6	94.49 (16)	Cl5—C6—Cl6	109.1 (4)
O12—Fe2—O6	166.89 (17)	C5—C6—H6	109.5
O9—Fe2—O6	88.4 (2)	Cl5—C6—H6	109.5
O13—Fe2—O4	94.61 (16)	Cl6—C6—H6	109.5
O12—Fe2—O4	87.6 (2)	O8—C7—O7	128.3 (5)
O9—Fe2—O4	167.81 (17)	O8—C7—C8	121.0 (5)
O6—Fe2—O4	90.4 (2)	O7—C7—C8	110.7 (5)
O13—Fe2—O14	175.47 (16)	C7—C8—Cl8	114.3 (5)
O12—Fe2—O14	84.51 (17)	C7—C8—Cl7	105.4 (5)
O9—Fe2—O14	85.66 (17)	Cl8—C8—Cl7	110.5 (4)
O6—Fe2—O14	82.38 (16)	C7—C8—H8	108.8
O4—Fe2—O14	82.17 (17)	Cl8—C8—H8	108.8
O13—Fe3—O2	91.27 (14)	Cl7—C8—H8	108.8
O13—Fe3—O11	94.02 (15)	O9—C9—O10	127.3 (5)
O2—Fe3—O11	96.35 (18)	O9—C9—C10	113.6 (5)
O13—Fe3—O2w	177.25 (15)	O10—C9—C10	119.1 (5)
O2—Fe3—O2w	86.15 (16)	C9—C10—Cl9	113.7 (4)
O11—Fe3—O2w	87.23 (16)	C9—C10—Cl10	111.5 (4)
O13—Fe3—O10	92.63 (14)	Cl9—C10—Cl10	111.7 (4)
O2—Fe3—O10	172.53 (16)	C9—C10—H10	106.5
O11—Fe3—O10	89.72 (17)	Cl9—C10—H10	106.5
O2w—Fe3—O10	89.82 (15)	Cl10—C10—H10	106.5
O13—Fe3—O8	93.57 (14)	O11—C11—O12	129.2 (5)
O2—Fe3—O8	85.85 (17)	O11—C11—C12	115.5 (5)
O11—Fe3—O8	172.04 (15)	O12—C11—C12	115.3 (5)
O2w—Fe3—O8	85.28 (15)	C11—C12—Cl11	111.3 (5)
O10—Fe3—O8	87.56 (15)	C11—C12—Cl12	107.9 (5)
C1—O1—Fe1	128.2 (4)	Cl11—C12—Cl12	111.4 (4)
C1—O2—Fe3	134.2 (4)	C11—C12—H12a	108.7
C3—O3—Fe1	129.1 (3)	Cl11—C12—H12a	108.7
C3—O4—Fe2	130.9 (4)	Cl12—C12—H12a	108.7
C5—O5—Fe1	128.3 (4)	O14—C13—C14	106.2 (8)
C5—O6—Fe2	132.2 (4)	O14—C13—H13A	110.5
C7—O7—Fe1	134.5 (4)	C14—C13—H13A	110.5
C7—O8—Fe3	128.0 (3)	O14—C13—H13B	110.5
C9—O9—Fe2	135.5 (4)	C14—C13—H13B	110.5
C9—O10—Fe3	128.8 (4)	H13A—C13—H13B	108.7
C11—O11—Fe3	130.0 (4)	C15—C14—C13	97.9 (9)
C11—O12—Fe2	132.6 (4)	C15—C14—H14A	112.2
Fe1—O13—Fe2	123.79 (18)	C13—C14—H14A	112.2
Fe1—O13—Fe3	118.50 (16)	C15—C14—H14B	112.2
Fe2—O13—Fe3	117.70 (17)	C13—C14—H14B	112.2
C16—O14—C13	108.7 (7)	H14A—C14—H14B	109.8
C16—O14—Fe2	127.9 (5)	C14—C15—C16	103.8 (10)
C13—O14—Fe2	123.3 (5)	C14—C15—H15A	111.0
Fe1—O1w—H11	121 (4)	C16—C15—H15A	111.0
Fe1—O1w—H12	124 (4)	C14—C15—H15B	111.0
H11—O1w—H12	107.6 (17)	C16—C15—H15B	111.0
Fe3—O2w—H21	119 (6)	H15A—C15—H15B	109.0
Fe3—O2w—H22	114 (7)	O14—C16—C15	104.4 (8)
H21—O2w—H22	107.5 (18)	O14—C16—H16A	110.9
O2—C1—O1	129.0 (5)	C15—C16—H16A	110.9
O2—C1—C2	114.4 (5)	O14—C16—H16B	110.9
O1—C1—C2	116.5 (5)	C15—C16—H16B	110.9
C1—C2—Cl2	110.8 (5)	H16A—C16—H16B	108.9
C1—C2—Cl1	110.0 (5)

O13—Fe1—O1—C1	30.2 (5)	O3—Fe1—O13—Fe3	−134.8 (2)
O7—Fe1—O1—C1	−70.1 (5)	O12—Fe2—O13—Fe1	−135.3 (2)
O5—Fe1—O1—C1	−157.9 (6)	O9—Fe2—O13—Fe1	132.7 (2)
O3—Fe1—O1—C1	124.2 (5)	O6—Fe2—O13—Fe1	43.7 (3)
O1w—Fe1—O1—C1	−153.2 (5)	O4—Fe2—O13—Fe1	−47.0 (3)
O13—Fe3—O2—C1	−14.5 (6)	O12—Fe2—O13—Fe3	45.9 (2)
O11—Fe3—O2—C1	−108.7 (6)	O9—Fe2—O13—Fe3	−46.1 (2)
O2w—Fe3—O2—C1	164.6 (6)	O6—Fe2—O13—Fe3	−135.1 (2)
O8—Fe3—O2—C1	79.0 (6)	O4—Fe2—O13—Fe3	134.2 (2)
O13—Fe1—O3—C3	−16.7 (5)	O2—Fe3—O13—Fe1	43.2 (2)
O7—Fe1—O3—C3	176.6 (6)	O11—Fe3—O13—Fe1	139.6 (2)
O1—Fe1—O3—C3	−115.2 (5)	O10—Fe3—O13—Fe1	−130.5 (2)
O5—Fe1—O3—C3	79.3 (5)	O8—Fe3—O13—Fe1	−42.8 (2)
O1w—Fe1—O3—C3	160.8 (5)	O2—Fe3—O13—Fe2	−138.0 (2)
O13—Fe2—O4—C3	18.4 (6)	O11—Fe3—O13—Fe2	−41.5 (2)
O12—Fe2—O4—C3	116.8 (6)	O10—Fe3—O13—Fe2	48.4 (2)
O9—Fe2—O4—C3	−160.3 (8)	O8—Fe3—O13—Fe2	136.1 (2)
O6—Fe2—O4—C3	−76.2 (6)	O12—Fe2—O14—C13	139.5 (9)
O14—Fe2—O4—C3	−158.4 (6)	O9—Fe2—O14—C13	−129.2 (9)
O13—Fe1—O5—C5	19.9 (5)	O6—Fe2—O14—C13	−40.2 (9)
O7—Fe1—O5—C5	120.1 (5)	O4—Fe2—O14—C13	51.2 (9)
O1—Fe1—O5—C5	−152.1 (7)	Fe3—O2—C1—O1	−4.6 (10)
O3—Fe1—O5—C5	−75.2 (5)	Fe3—O2—C1—C2	176.5 (5)
O1w—Fe1—O5—C5	−156.9 (5)	Fe1—O1—C1—C2	175.7 (4)
O13—Fe2—O6—C5	−13.1 (6)	O2—C1—C2—Cl2	114.7 (6)
O12—Fe2—O6—C5	162.4 (8)	O1—C1—C2—Cl2	−64.4 (7)
O9—Fe2—O6—C5	−110.6 (6)	O2—C1—C2—Cl1	−122.3 (5)
O4—Fe2—O6—C5	81.6 (6)	O1—C1—C2—Cl1	58.7 (7)
O14—Fe2—O6—C5	163.6 (6)	Fe2—O4—C3—C4	−172.8 (5)
O13—Fe1—O7—C7	−23.4 (6)	Fe1—O3—C3—O4	−7.7 (9)
O1—Fe1—O7—C7	75.7 (6)	Fe1—O3—C3—C4	171.8 (4)
O5—Fe1—O7—C7	−119.2 (6)	O4—C3—C4—Cl3	−41.7 (8)
O3—Fe1—O7—C7	143.2 (6)	O3—C3—C4—Cl3	138.7 (5)
O1w—Fe1—O7—C7	159.0 (6)	O4—C3—C4—Cl4	79.4 (6)
O13—Fe3—O8—C7	28.5 (5)	O3—C3—C4—Cl4	−100.2 (5)
O2—Fe3—O8—C7	−62.6 (5)	Fe1—O5—C5—C6	−173.3 (5)
O2w—Fe3—O8—C7	−149.0 (5)	Fe2—O6—C5—C6	169.0 (5)
O10—Fe3—O8—C7	120.9 (5)	O5—C5—C6—Cl5	−97.9 (6)
O13—Fe2—O9—C9	18.2 (6)	O6—C5—C6—Cl5	82.8 (7)
O12—Fe2—O9—C9	−80.6 (6)	O5—C5—C6—Cl6	142.3 (5)
O6—Fe2—O9—C9	112.5 (6)	O6—C5—C6—Cl6	−37.0 (8)
O4—Fe2—O9—C9	−163.2 (8)	Fe3—O8—C7—O7	−13.7 (9)
O14—Fe2—O9—C9	−165.0 (6)	Fe3—O8—C7—C8	165.3 (4)
O13—Fe3—O10—C9	−25.7 (5)	Fe1—O7—C7—C8	−169.9 (5)
O11—Fe3—O10—C9	68.3 (5)	O8—C7—C8—Cl8	20.3 (8)
O2w—Fe3—O10—C9	155.5 (5)	O7—C7—C8—Cl8	−160.5 (5)
O8—Fe3—O10—C9	−119.2 (5)	O8—C7—C8—Cl7	−101.2 (6)
O13—Fe3—O11—C11	17.7 (5)	O7—C7—C8—Cl7	78.0 (6)
O2—Fe3—O11—C11	109.4 (5)	Fe2—O9—C9—C10	−171.7 (5)
O2w—Fe3—O11—C11	−164.8 (5)	Fe3—O10—C9—O9	1.0 (9)
O10—Fe3—O11—C11	−74.9 (5)	Fe3—O10—C9—C10	178.3 (4)
O13—Fe2—O12—C11	−30.9 (6)	O9—C9—C10—Cl9	−171.3 (5)
O9—Fe2—O12—C11	66.9 (6)	O10—C9—C10—Cl9	11.0 (7)
O6—Fe2—O12—C11	153.6 (8)	O9—C9—C10—Cl10	−44.0 (7)
O4—Fe2—O12—C11	−125.2 (6)	O10—C9—C10—Cl10	138.4 (5)
O14—Fe2—O12—C11	152.4 (6)	Fe3—O11—C11—C12	176.9 (4)
O7—Fe1—O13—Fe2	−137.2 (2)	Fe2—O12—C11—C12	−170.4 (4)
O1—Fe1—O13—Fe2	131.6 (2)	O11—C11—C12—Cl11	131.1 (5)
O5—Fe1—O13—Fe2	−46.3 (2)	O12—C11—C12—Cl11	−49.9 (7)
O3—Fe1—O13—Fe2	46.4 (2)	O11—C11—C12—Cl12	−106.4 (6)
O7—Fe1—O13—Fe3	41.6 (2)	O12—C11—C12—Cl12	72.7 (6)
O1—Fe1—O13—Fe3	−49.6 (2)	Fe2—O14—C13—C14	−157.0 (8)
O5—Fe1—O13—Fe3	132.5 (2)	Fe2—O14—C16—C15	−175.9 (8)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1w—H11···O3ⁱ	0.85 (1)	2.01 (3)	2.809 (6)	158 (5)
O2w—H22···O8ⁱⁱ	0.85 (1)	2.06 (4)	2.821 (5)	149 (7)
O2W—H21···O10ⁱⁱ	0.84 (6)	2.19 (7)	2.950 (6)	150 (6)
O1W—H12···Cl1ⁱ	0.85 (3)	2.47 (4)	3.288 (4)	160 (6)

Symmetry codes: (i) −x+1, −y+1, −z; (ii) −x+1, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	[Fe₂Mn(C₂HCl₂O₂)₆O(C₄H₈O)(H₂O)₂]
M_r	1058.34
Crystal system, space group	Triclinic, P1
Temperature (K)	295
a, b, c (Å)	9.380 (1), 13.316 (1), 15.432 (1)
α, β, γ (°)	90.131 (1), 100.067 (1), 97.677 (1)
V (Å³)	1880.1 (2)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	2.01
Crystal size (mm)	0.35 × 0.15 × 0.15

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.540, 0.753
No. of measured, independent and observed [I > 2σ(I)] reflections	15425, 8543, 5788
R_int	0.025
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.063, 0.207, 1.03
No. of reflections	8543
No. of parameters	440
No. of restraints	35
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	1.64, −0.90

Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1w—H11···O3ⁱ	0.85 (1)	2.01 (3)	2.809 (6)	158 (5)
O2w—H22···O8ⁱⁱ	0.85 (1)	2.06 (4)	2.821 (5)	149 (7)
O2W—H21···O10ⁱⁱ	0.84 (6)	2.19 (7)	2.950 (6)	150 (6)
O1W—H12···Cl1ⁱ	0.85 (3)	2.47 (4)	3.288 (4)	160 (6)

Symmetry codes: (i) −x+1, −y+1, −z; (ii) −x+1, −y+1, −z+1.

Acknowledgements

The authors thank Shahid Beheshti University and the University of Malaya for supporting this study.

References

Amini, M. M., Yadavi, M. & Ng, S. W. (2004a). Acta Cryst. E60, m492–m494. Web of Science CSD CrossRef IUCr Journals Google Scholar
Amini, M. M., Yadavi, M. & Ng, S. W. (2004b). Acta Cryst. E60, m495–m497. Web of Science CSD CrossRef IUCr Journals Google Scholar
Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. 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. (2010). publCIF. In preparation. Google Scholar

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