Bis(2-{5-[(2-carb­oxy­phen­yl)sulfanylmeth­yl]-2,4-dimethyl­benzyl­sulfan­yl}benzoato-κ2O,O′)bis­(pyridine-κN)iron(II)

Xu, Y.-M.; Hu, T.-P.

doi:10.1107/S1600536810054619

metal-organic compounds

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Volume 67| Part 2| February 2011| Page m159

doi:10.1107/S1600536810054619

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Bis(2-{5-[(2-carboxyphenyl)sulfanylmethyl]-2,4-dimethylbenzylsulfanyl}benzoato-κ²O,O′)bis(pyridine-κN)iron(II)

Yu-Min Xu ^a ^* and Tuo-Ping Hu ^a

^aDepartment of Chemistry, North University of China, Taiyuan 030051, People's Republic of China
^*Correspondence e-mail: yuminzaizher@126.com

(Received 20 December 2010; accepted 29 December 2010; online 12 January 2011)

The title compound, [Fe(C₂₄H₂₁O₄S₂)₂(C₅H₅N)₂], has 2 symmetry. The Fe^II cation is located on a twofold rotation axis and is O,O′-chelated by two 2-{5-[(2-carboxyphenyl)sulfanylmethyl]-2,4-dimethylbenzylsulfanyl}benzoate anions and further coordinated by two pyridine ligands in a distorted octahedral geometry. In the anion, the terminal benzene rings are oriented at dihedral angles of 63.81 (14) and 84.50 (14)° with respect to the central benzene ring. Intermolecular O—H⋯O and C—H⋯O hydrogen bonding is present in the crystal structure.

Related literature

For applications of multithioether ligands in inorganic chemistry, see: Li et al. (2002 ). For structures of related complexes with multithioether ligands, see: Bu et al. (2002 ); Alcock et al. (1978 ) and with carboxylate ligands, see: Dai et al. (2008 ).

Experimental

Crystal data

[Fe(C₂₄H₂₁O₄S₂)₂(C₅H₅N)₂]
M_r = 1089.10
Orthorhombic, P b c n
a = 16.987 (5) Å
b = 9.635 (3) Å
c = 31.982 (10) Å
V = 5234 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.51 mm⁻¹
T = 293 K
0.15 × 0.10 × 0.10 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.928, T_max = 0.951
29090 measured reflections
5950 independent reflections
3431 reflections with I > 2σ(I)
R_int = 0.073

Refinement

R[F² > 2σ(F²)] = 0.047
wR(F²) = 0.114
S = 1.00
5950 reflections
336 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.29 e Å⁻³
Δρ_min = −0.24 e Å⁻³

Table 1
Selected bond lengths (Å)

Fe1—O1	2.412 (2)
Fe1—O2	2.0400 (18)
Fe1—N1	2.100 (2)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H4⋯O1ⁱ	0.96 (4)	1.77 (4)	2.702 (3)	162 (4)
C16—H16A⋯O3ⁱⁱ	0.93	2.54	3.421 (3)	158
Symmetry codes: (i) $[x-{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[-x-{\script{1\over 2}}, y+{\script{1\over 2}}, z]$ .

Data collection: APEX2 (Bruker, 2007 ); cell refinement: SAINT-Plus (Bruker, 2007); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810054619/xu5127sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810054619/xu5127Isup2.hkl

checkCIF report

Comment top

Multithioether ligands possess unusual potential for structure control in inorganic chemistry (Li et al., 2002). Some crystal structures of complexes with multithioether ligands have been reported previously (Bu et al., 2002; Alcock et al., 1978). The title compound with the flexible multithioether ligand was obtained in preparing of metal-organic framework (MOF) compounds.

In (I), the central Fe²⁺ ion is coordinated by four oxygen atoms from the carboxylate group of the ligand and two nitrogen atoms from the pyridine molecule in a distorted octahedron (Fig. 1).

The asymmetry unit contains one ligand, one pyridine molecule, and half Fe²⁺ ion sitting on the twofold axis, with the other part being generated by the symmetry operation of C<ι>₂.

Strong H-bondings are observed between the O-H group of the carboxylate group and O2 in the crystal structure (Table 2).

Related literature top

For applications of multithioether ligands in inorganic chemistry, see: Li et al. (2002). For structures of related complexes with multithioether ligands, see: Bu et al. (2002); Alcock et al. (1978). For related literature [on what subject?], see: Dai et al. (2009).

Experimental top

2,4-Bis(2-(benzylacid)thiophenylmethyl)-1,5-dimethylbenze (2 mg, 4.6 mmol) and FeSO₄ (4 mg, 26.3 mmol) were dissolved in 1 ml mixed solution of H2O, DMF and MeOH (5:3:2), then 1 drop pyridine was added. The mixed solution was sealed into a Pyrex glass tube. The mixed solution was heated at 363 K for 60 h, and then cooled down to room temperature over 17 h. Orange crystals were obtained from the reaction mixture.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT-Plus (Bruker, 2007); data reduction: SAINT-Plus (Bruker, 2007); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. Molecular structure showing 35% probability displacement ellipsoids. The atoms marked with A are derived from the reference atoms by the symmetry transformation of (-x, y, z).

Bis(2-{5-[(2-carboxyphenyl)sulfanylmethyl]-2,4-dimethylbenzylsulfanyl}benzoato-κ²O,O')bis(pyridine-κN)iron(II) top

Crystal data top

[Fe(C₂₄H₂₁O₄S₂)₂(C₅H₅N)₂]	F(000) = 2272
M_r = 1089.10	D_x = 1.382 Mg m⁻³
Orthorhombic, Pbcn	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2n 2ab	Cell parameters from 3184 reflections
a = 16.987 (5) Å	θ = 2.4–20.3°
b = 9.635 (3) Å	µ = 0.51 mm⁻¹
c = 31.982 (10) Å	T = 293 K
V = 5234 (3) Å³	Prism, orange
Z = 4	0.15 × 0.10 × 0.10 mm

Data collection top

Bruker APEXII CCD area-detector diffractometer	5950 independent reflections
Radiation source: fine-focus sealed tube	3431 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.073
ϕ and ω scans	θ_max = 27.4°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −22→18
T_min = 0.928, T_max = 0.951	k = −11→12
29090 measured reflections	l = −40→41

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.114	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ²(F_o²) + (0.0476P)² + 0.3652P] where P = (F_o² + 2F_c²)/3
5950 reflections	(Δ/σ)_max < 0.001
336 parameters	Δρ_max = 0.29 e Å⁻³
0 restraints	Δρ_min = −0.24 e Å⁻³

Crystal data top

[Fe(C₂₄H₂₁O₄S₂)₂(C₅H₅N)₂]	V = 5234 (3) Å³
M_r = 1089.10	Z = 4
Orthorhombic, Pbcn	Mo Kα radiation
a = 16.987 (5) Å	µ = 0.51 mm⁻¹
b = 9.635 (3) Å	T = 293 K
c = 31.982 (10) Å	0.15 × 0.10 × 0.10 mm

Data collection top

Bruker APEXII CCD area-detector diffractometer	5950 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3431 reflections with I > 2σ(I)
T_min = 0.928, T_max = 0.951	R_int = 0.073
29090 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	0 restraints
wR(F²) = 0.114	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	Δρ_max = 0.29 e Å⁻³
5950 reflections	Δρ_min = −0.24 e Å⁻³
336 parameters

Special details top

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.

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

	x	y	z	U_iso*/U_eq
Fe1	0.0000	0.74627 (6)	0.2500	0.04331 (16)
S2	−0.30599 (4)	0.78127 (7)	0.40440 (2)	0.04618 (19)
S3	0.04300 (4)	0.89147 (7)	0.38414 (2)	0.0475 (2)
N1	0.08272 (13)	0.6062 (2)	0.22545 (7)	0.0479 (6)
O1	0.09558 (11)	0.9313 (2)	0.25198 (6)	0.0540 (5)
O2	0.05286 (11)	0.8060 (2)	0.30437 (5)	0.0499 (5)
O3	−0.35938 (12)	0.5896 (2)	0.34618 (6)	0.0610 (6)
O4	−0.45225 (12)	0.6383 (2)	0.29905 (6)	0.0617 (6)
C1	0.09241 (15)	0.9076 (3)	0.29042 (8)	0.0417 (6)
C2	0.13707 (15)	0.9951 (3)	0.32090 (8)	0.0396 (6)
C3	0.19723 (17)	1.0779 (3)	0.30537 (10)	0.0575 (8)
H3A	0.2079	1.0777	0.2768	0.069*
C4	0.2413 (2)	1.1602 (4)	0.33156 (11)	0.0749 (10)
H4A	0.2820	1.2143	0.3209	0.090*
C5	0.22487 (19)	1.1615 (4)	0.37331 (11)	0.0755 (10)
H5A	0.2546	1.2171	0.3911	0.091*
C6	0.16505 (17)	1.0818 (3)	0.38954 (10)	0.0582 (8)
H6A	0.1545	1.0856	0.4180	0.070*
C7	0.12002 (14)	0.9957 (3)	0.36411 (8)	0.0401 (6)
C8	0.02048 (16)	0.9718 (3)	0.43415 (8)	0.0519 (8)
H8A	0.0658	0.9674	0.4525	0.062*
H8B	0.0062	1.0684	0.4302	0.062*
C9	−0.04780 (15)	0.8916 (3)	0.45280 (8)	0.0409 (6)
C10	−0.03712 (15)	0.7868 (3)	0.48216 (8)	0.0426 (6)
C11	0.04427 (16)	0.7410 (3)	0.49569 (10)	0.0642 (9)
H11A	0.0403	0.6564	0.5114	0.096*
H11B	0.0676	0.8118	0.5128	0.096*
H11C	0.0764	0.7259	0.4714	0.096*
C12	−0.10259 (15)	0.7253 (3)	0.49995 (8)	0.0437 (7)
H12A	−0.0950	0.6574	0.5202	0.052*
C13	−0.17944 (14)	0.7601 (3)	0.48894 (8)	0.0400 (6)
C14	−0.24754 (16)	0.6930 (3)	0.51124 (9)	0.0556 (8)
H14A	−0.2286	0.6178	0.5282	0.083*
H14B	−0.2844	0.6580	0.4911	0.083*
H14C	−0.2731	0.7603	0.5287	0.083*
C15	−0.19034 (15)	0.8607 (3)	0.45766 (8)	0.0394 (6)
C16	−0.12421 (15)	0.9235 (3)	0.44033 (8)	0.0436 (7)
H16A	−0.1314	0.9896	0.4195	0.052*
C17	−0.27102 (14)	0.9053 (3)	0.44325 (8)	0.0452 (7)
H17A	−0.2684	0.9975	0.4311	0.054*
H17B	−0.3069	0.9080	0.4668	0.054*
C18	−0.40055 (15)	0.8453 (3)	0.39068 (8)	0.0393 (6)
C19	−0.43241 (17)	0.9630 (3)	0.40961 (9)	0.0493 (7)
H19A	−0.4036	1.0091	0.4301	0.059*
C20	−0.50547 (18)	1.0123 (3)	0.39868 (9)	0.0584 (8)
H20A	−0.5250	1.0916	0.4116	0.070*
C21	−0.55010 (18)	0.9458 (4)	0.36882 (10)	0.0642 (9)
H21A	−0.6002	0.9779	0.3622	0.077*
C22	−0.51971 (17)	0.8319 (3)	0.34908 (9)	0.0535 (8)
H22A	−0.5494	0.7876	0.3286	0.064*
C23	−0.44520 (15)	0.7808 (3)	0.35894 (8)	0.0400 (6)
C24	−0.41396 (17)	0.6604 (3)	0.33493 (9)	0.0453 (7)
C25	0.12280 (17)	0.6396 (3)	0.19087 (9)	0.0557 (8)
H25A	0.1064	0.7160	0.1754	0.067*
C26	0.18633 (19)	0.5669 (4)	0.17738 (11)	0.0692 (9)
H26A	0.2131	0.5947	0.1534	0.083*
C27	0.2106 (2)	0.4539 (4)	0.19880 (13)	0.0750 (10)
H27A	0.2545	0.4041	0.1901	0.090*
C28	0.1694 (2)	0.4137 (4)	0.23362 (13)	0.0778 (11)
H28A	0.1840	0.3350	0.2486	0.093*
C29	0.1056 (2)	0.4935 (4)	0.24592 (10)	0.0650 (9)
H29A	0.0776	0.4668	0.2696	0.078*
H4	−0.428 (2)	0.561 (4)	0.2852 (12)	0.124 (16)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Fe1	0.0466 (3)	0.0494 (3)	0.0340 (3)	0.000	0.0038 (3)	0.000
S2	0.0433 (4)	0.0469 (4)	0.0484 (4)	0.0056 (3)	−0.0105 (3)	−0.0091 (3)
S3	0.0501 (4)	0.0531 (4)	0.0393 (4)	−0.0149 (4)	0.0100 (3)	−0.0041 (3)
N1	0.0503 (14)	0.0503 (14)	0.0429 (14)	0.0007 (12)	0.0031 (11)	0.0009 (12)
O1	0.0674 (13)	0.0589 (13)	0.0357 (11)	0.0015 (10)	0.0065 (10)	0.0067 (10)
O2	0.0601 (13)	0.0514 (12)	0.0382 (11)	−0.0130 (10)	0.0019 (9)	0.0003 (9)
O3	0.0561 (13)	0.0642 (13)	0.0627 (14)	0.0133 (11)	−0.0122 (11)	−0.0187 (11)
O4	0.0714 (15)	0.0633 (14)	0.0503 (13)	0.0041 (12)	−0.0190 (11)	−0.0164 (11)
C1	0.0415 (16)	0.0433 (16)	0.0403 (17)	0.0086 (13)	0.0076 (13)	0.0033 (13)
C2	0.0367 (15)	0.0372 (15)	0.0447 (16)	0.0035 (12)	0.0043 (12)	0.0057 (12)
C3	0.0578 (19)	0.0573 (19)	0.0572 (19)	−0.0092 (16)	0.0151 (16)	0.0032 (15)
C4	0.066 (2)	0.080 (2)	0.079 (3)	−0.0352 (19)	0.021 (2)	0.000 (2)
C5	0.064 (2)	0.089 (3)	0.074 (2)	−0.038 (2)	0.0041 (18)	−0.015 (2)
C6	0.0551 (19)	0.069 (2)	0.0500 (18)	−0.0194 (16)	0.0049 (15)	−0.0061 (16)
C7	0.0343 (15)	0.0415 (15)	0.0446 (16)	−0.0018 (12)	0.0030 (12)	−0.0001 (12)
C8	0.0484 (18)	0.0641 (19)	0.0432 (17)	−0.0151 (15)	0.0091 (13)	−0.0108 (15)
C9	0.0411 (16)	0.0500 (16)	0.0315 (14)	−0.0089 (13)	0.0049 (12)	−0.0065 (13)
C10	0.0353 (15)	0.0589 (17)	0.0338 (15)	−0.0024 (13)	−0.0019 (12)	−0.0091 (13)
C11	0.0410 (17)	0.092 (2)	0.059 (2)	0.0014 (17)	−0.0071 (15)	0.0007 (18)
C12	0.0450 (16)	0.0540 (17)	0.0320 (14)	−0.0026 (13)	−0.0015 (12)	0.0045 (12)
C13	0.0360 (15)	0.0489 (16)	0.0350 (15)	−0.0041 (12)	0.0016 (11)	−0.0074 (13)
C14	0.0441 (17)	0.073 (2)	0.0497 (18)	−0.0077 (15)	0.0059 (14)	0.0017 (15)
C15	0.0391 (15)	0.0421 (15)	0.0369 (15)	0.0007 (12)	−0.0028 (12)	−0.0064 (12)
C16	0.0495 (18)	0.0441 (16)	0.0373 (15)	−0.0046 (13)	0.0004 (13)	−0.0020 (12)
C17	0.0403 (16)	0.0495 (16)	0.0459 (16)	−0.0013 (13)	−0.0059 (12)	−0.0063 (13)
C18	0.0406 (15)	0.0393 (15)	0.0379 (15)	−0.0016 (12)	−0.0013 (12)	0.0030 (12)
C19	0.0554 (19)	0.0470 (17)	0.0455 (17)	0.0052 (14)	−0.0052 (14)	−0.0060 (14)
C20	0.064 (2)	0.0540 (18)	0.058 (2)	0.0218 (16)	−0.0026 (16)	−0.0052 (15)
C21	0.053 (2)	0.070 (2)	0.070 (2)	0.0189 (17)	−0.0132 (17)	0.0002 (18)
C22	0.0482 (18)	0.0578 (19)	0.0544 (19)	0.0003 (15)	−0.0136 (14)	−0.0019 (16)
C23	0.0406 (15)	0.0391 (15)	0.0401 (15)	−0.0011 (12)	−0.0001 (12)	0.0027 (12)
C24	0.0423 (17)	0.0480 (17)	0.0457 (18)	−0.0079 (14)	−0.0008 (14)	−0.0030 (14)
C25	0.0549 (19)	0.062 (2)	0.0505 (19)	−0.0042 (16)	0.0085 (15)	0.0024 (15)
C26	0.053 (2)	0.087 (3)	0.068 (2)	0.001 (2)	0.0125 (17)	−0.015 (2)
C27	0.055 (2)	0.082 (3)	0.088 (3)	0.012 (2)	−0.004 (2)	−0.029 (2)
C28	0.075 (3)	0.064 (2)	0.095 (3)	0.011 (2)	−0.028 (2)	0.002 (2)
C29	0.070 (2)	0.068 (2)	0.057 (2)	0.0068 (18)	0.0022 (17)	0.0139 (18)

Geometric parameters (Å, º) top

Fe1—O1	2.412 (2)	C11—H11A	0.9600
Fe1—O1ⁱ	2.412 (2)	C11—H11B	0.9600
Fe1—O2ⁱ	2.0400 (18)	C11—H11C	0.9600
Fe1—O2	2.0400 (18)	C12—C13	1.393 (3)
Fe1—N1ⁱ	2.100 (2)	C12—H12A	0.9300
Fe1—N1	2.100 (2)	C13—C15	1.405 (3)
S2—C18	1.776 (3)	C13—C14	1.505 (4)
S2—C17	1.823 (3)	C14—H14A	0.9600
S3—C7	1.769 (3)	C14—H14B	0.9600
S3—C8	1.818 (3)	C14—H14C	0.9600
N1—C29	1.327 (4)	C15—C16	1.391 (3)
N1—C25	1.338 (3)	C15—C17	1.508 (3)
O1—C1	1.252 (3)	C16—H16A	0.9300
O2—C1	1.268 (3)	C17—H17A	0.9700
O3—C24	1.206 (3)	C17—H17B	0.9700
O4—C24	1.336 (3)	C18—C19	1.395 (4)
O4—H4	0.96 (4)	C18—C23	1.411 (3)
C1—C2	1.496 (4)	C19—C20	1.374 (4)
C2—C3	1.388 (4)	C19—H19A	0.9300
C2—C7	1.412 (4)	C20—C21	1.377 (4)
C3—C4	1.375 (4)	C20—H20A	0.9300
C3—H3A	0.9300	C21—C22	1.367 (4)
C4—C5	1.365 (4)	C21—H21A	0.9300
C4—H4A	0.9300	C22—C23	1.394 (4)
C5—C6	1.375 (4)	C22—H22A	0.9300
C5—H5A	0.9300	C23—C24	1.489 (4)
C6—C7	1.391 (4)	C25—C26	1.357 (4)
C6—H6A	0.9300	C25—H25A	0.9300
C8—C9	1.516 (3)	C26—C27	1.350 (5)
C8—H8A	0.9700	C26—H26A	0.9300
C8—H8B	0.9700	C27—C28	1.370 (5)
C9—C16	1.392 (3)	C27—H27A	0.9300
C9—C10	1.391 (4)	C28—C29	1.386 (5)
C10—C12	1.383 (4)	C28—H28A	0.9300
C10—C11	1.514 (4)	C29—H29A	0.9300

O2ⁱ—Fe1—O2	147.21 (11)	C12—C13—C14	119.8 (2)
O2ⁱ—Fe1—N1ⁱ	101.86 (8)	C15—C13—C14	122.2 (2)
O2—Fe1—N1ⁱ	99.04 (8)	C13—C14—H14A	109.5
O2ⁱ—Fe1—N1	99.04 (8)	C13—C14—H14B	109.5
O2—Fe1—N1	101.86 (8)	H14A—C14—H14B	109.5
N1ⁱ—Fe1—N1	100.07 (13)	C13—C14—H14C	109.5
C18—S2—C17	103.62 (12)	H14A—C14—H14C	109.5
C7—S3—C8	103.45 (13)	H14B—C14—H14C	109.5
C29—N1—C25	117.1 (3)	C16—C15—C13	118.5 (2)
C29—N1—Fe1	122.5 (2)	C16—C15—C17	119.2 (2)
C25—N1—Fe1	119.7 (2)	C13—C15—C17	122.2 (2)
C1—O2—Fe1	98.68 (16)	C15—C16—C9	122.9 (3)
C24—O4—H4	108 (2)	C15—C16—H16A	118.5
O1—C1—O2	120.6 (3)	C9—C16—H16A	118.5
O1—C1—C2	121.0 (2)	C15—C17—S2	108.51 (18)
O2—C1—C2	118.3 (2)	C15—C17—H17A	110.0
C3—C2—C7	119.9 (3)	S2—C17—H17A	110.0
C3—C2—C1	117.7 (2)	C15—C17—H17B	110.0
C7—C2—C1	122.4 (2)	S2—C17—H17B	110.0
C4—C3—C2	121.0 (3)	H17A—C17—H17B	108.4
C4—C3—H3A	119.5	C19—C18—C23	117.5 (2)
C2—C3—H3A	119.5	C19—C18—S2	121.7 (2)
C5—C4—C3	119.3 (3)	C23—C18—S2	120.7 (2)
C5—C4—H4A	120.3	C20—C19—C18	121.4 (3)
C3—C4—H4A	120.3	C20—C19—H19A	119.3
C4—C5—C6	121.0 (3)	C18—C19—H19A	119.3
C4—C5—H5A	119.5	C19—C20—C21	120.9 (3)
C6—C5—H5A	119.5	C19—C20—H20A	119.6
C5—C6—C7	121.3 (3)	C21—C20—H20A	119.6
C5—C6—H6A	119.4	C22—C21—C20	119.1 (3)
C7—C6—H6A	119.4	C22—C21—H21A	120.5
C6—C7—C2	117.5 (2)	C20—C21—H21A	120.5
C6—C7—S3	122.3 (2)	C21—C22—C23	121.5 (3)
C2—C7—S3	120.3 (2)	C21—C22—H22A	119.3
C9—C8—S3	106.88 (18)	C23—C22—H22A	119.3
C9—C8—H8A	110.3	C22—C23—C18	119.7 (2)
S3—C8—H8A	110.3	C22—C23—C24	118.8 (2)
C9—C8—H8B	110.3	C18—C23—C24	121.5 (2)
S3—C8—H8B	110.3	O3—C24—O4	122.7 (3)
H8A—C8—H8B	108.6	O3—C24—C23	124.1 (2)
C16—C9—C10	118.3 (2)	O4—C24—C23	113.2 (3)
C16—C9—C8	119.3 (3)	N1—C25—C26	122.9 (3)
C10—C9—C8	122.4 (2)	N1—C25—H25A	118.5
C12—C10—C9	119.0 (2)	C26—C25—H25A	118.5
C12—C10—C11	119.5 (3)	C27—C26—C25	119.8 (3)
C9—C10—C11	121.6 (3)	C27—C26—H26A	120.1
C10—C11—H11A	109.5	C25—C26—H26A	120.1
C10—C11—H11B	109.5	C26—C27—C28	119.0 (3)
H11A—C11—H11B	109.5	C26—C27—H27A	120.5
C10—C11—H11C	109.5	C28—C27—H27A	120.5
H11A—C11—H11C	109.5	C27—C28—C29	118.2 (3)
H11B—C11—H11C	109.5	C27—C28—H28A	120.9
C10—C12—C13	123.1 (3)	C29—C28—H28A	120.9
C10—C12—H12A	118.4	N1—C29—C28	122.9 (3)
C13—C12—H12A	118.4	N1—C29—H29A	118.5
C12—C13—C15	118.0 (2)	C28—C29—H29A	118.5

O2ⁱ—Fe1—N1—C29	−146.8 (2)	C10—C12—C13—C14	−177.2 (2)
O2—Fe1—N1—C29	58.7 (2)	C12—C13—C15—C16	−2.1 (4)
N1ⁱ—Fe1—N1—C29	−42.9 (2)	C14—C13—C15—C16	176.3 (2)
O2ⁱ—Fe1—N1—C25	43.1 (2)	C12—C13—C15—C17	179.6 (2)
O2—Fe1—N1—C25	−111.5 (2)	C14—C13—C15—C17	−1.9 (4)
N1ⁱ—Fe1—N1—C25	147.0 (2)	C13—C15—C16—C9	−0.4 (4)
O2ⁱ—Fe1—O2—C1	−39.76 (14)	C17—C15—C16—C9	177.9 (2)
N1ⁱ—Fe1—O2—C1	−168.90 (15)	C10—C9—C16—C15	3.8 (4)
N1—Fe1—O2—C1	88.73 (16)	C8—C9—C16—C15	−176.1 (2)
Fe1—O2—C1—O1	−7.3 (3)	C16—C15—C17—S2	98.4 (2)
Fe1—O2—C1—C2	174.59 (18)	C13—C15—C17—S2	−83.3 (3)
O1—C1—C2—C3	−16.7 (4)	C18—S2—C17—C15	179.62 (18)
O2—C1—C2—C3	161.4 (2)	C17—S2—C18—C19	−1.8 (3)
O1—C1—C2—C7	163.4 (2)	C17—S2—C18—C23	176.1 (2)
O2—C1—C2—C7	−18.5 (4)	C23—C18—C19—C20	1.8 (4)
C7—C2—C3—C4	0.6 (4)	S2—C18—C19—C20	179.7 (2)
C1—C2—C3—C4	−179.4 (3)	C18—C19—C20—C21	0.7 (5)
C2—C3—C4—C5	−0.8 (5)	C19—C20—C21—C22	−2.0 (5)
C3—C4—C5—C6	0.1 (6)	C20—C21—C22—C23	0.9 (5)
C4—C5—C6—C7	0.9 (6)	C21—C22—C23—C18	1.6 (4)
C5—C6—C7—C2	−1.2 (4)	C21—C22—C23—C24	−177.2 (3)
C5—C6—C7—S3	179.7 (3)	C19—C18—C23—C22	−2.9 (4)
C3—C2—C7—C6	0.4 (4)	S2—C18—C23—C22	179.2 (2)
C1—C2—C7—C6	−179.6 (2)	C19—C18—C23—C24	175.8 (2)
C3—C2—C7—S3	179.5 (2)	S2—C18—C23—C24	−2.1 (3)
C1—C2—C7—S3	−0.5 (3)	C22—C23—C24—O3	−163.3 (3)
C8—S3—C7—C6	19.2 (3)	C18—C23—C24—O3	18.0 (4)
C8—S3—C7—C2	−159.9 (2)	C22—C23—C24—O4	17.1 (4)
C7—S3—C8—C9	177.75 (19)	C18—C23—C24—O4	−161.6 (2)
S3—C8—C9—C16	−82.8 (3)	C29—N1—C25—C26	−2.6 (4)
S3—C8—C9—C10	97.3 (3)	Fe1—N1—C25—C26	168.0 (2)
C16—C9—C10—C12	−4.5 (4)	N1—C25—C26—C27	1.2 (5)
C8—C9—C10—C12	175.4 (2)	C25—C26—C27—C28	0.9 (5)
C16—C9—C10—C11	176.8 (2)	C26—C27—C28—C29	−1.6 (5)
C8—C9—C10—C11	−3.2 (4)	C25—N1—C29—C28	1.9 (5)
C9—C10—C12—C13	2.1 (4)	Fe1—N1—C29—C28	−168.5 (3)
C11—C10—C12—C13	−179.2 (3)	C27—C28—C29—N1	0.2 (5)
C10—C12—C13—C15	1.3 (4)

Symmetry code: (i) −x, y, −z+1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4···O1ⁱⁱ	0.96 (4)	1.77 (4)	2.702 (3)	162 (4)
C16—H16A···O3ⁱⁱⁱ	0.93	2.54	3.421 (3)	158

Symmetry codes: (ii) x−1/2, y−1/2, −z+1/2; (iii) −x−1/2, y+1/2, z.

Experimental details

Crystal data
Chemical formula	[Fe(C₂₄H₂₁O₄S₂)₂(C₅H₅N)₂]
M_r	1089.10
Crystal system, space group	Orthorhombic, Pbcn
Temperature (K)	293
a, b, c (Å)	16.987 (5), 9.635 (3), 31.982 (10)
V (Å³)	5234 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.51
Crystal size (mm)	0.15 × 0.10 × 0.10

Data collection
Diffractometer	Bruker APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.928, 0.951
No. of measured, independent and observed [I > 2σ(I)] reflections	29090, 5950, 3431
R_int	0.073
(sin θ/λ)_max (Å⁻¹)	0.648

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.114, 1.00
No. of reflections	5950
No. of parameters	336
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.29, −0.24

Computer programs: APEX2 (Bruker, 2007), SAINT-Plus (Bruker, 2007), SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top

Fe1—O1	2.412 (2)	Fe1—N1	2.100 (2)
Fe1—O2	2.0400 (18)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4···O1ⁱ	0.96 (4)	1.77 (4)	2.702 (3)	162 (4)
C16—H16A···O3ⁱⁱ	0.93	2.54	3.421 (3)	158

Symmetry codes: (i) x−1/2, y−1/2, −z+1/2; (ii) −x−1/2, y+1/2, z.

Acknowledgements

The author is grateful for funding support from the Natural Science foundation of Shanxi province, China (2007011033).

References

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