Buy article online - an online subscription or single-article purchase is required to access this article.
Download citation
Download citation
link to html
The crystal structure of the title compound, tris(1,10-phenanthroline-N,N')­iron(II) bis­[1,2-benziso­thia­zol-3(2H)-onate 1,1-dioxide] 1,2-benziso­thia­zol-3(2H)-one 1,1-dioxide hexahydrate, [Fe(C12H8N2)3](C7H4NO3S)2·C7H5NO3S·6H2O, at 120 K consists of slightly distorted octahedral [Fe(phen)3]2+ cations (phen is 1,10-phenanthroline), two saccharinate anions and a free saccharin mol­ecule, as well as six waters of crystallization. The compound has been confirmed as diamagnetic low-spin iron(II) by magnetic measurements. There is extensive hydrogen bonding leading to a three-dimensional network.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270100013093/bm1421sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270100013093/bm1421Isup2.hkl
Contains datablock I

CCDC reference: 158221

Comment top

In our earlier papers on metal-saccharinate complexes with the bidentate ligands 2,2'-bipyridine (bipy) or phen present (Dillon et al., 1999; Deng et al., 2000), we summarized previous work on these systems, including examples with all the saccharinate ligands attached to the metal (Hergold-Brundic et al., 1989) and ones where saccharinate is present only as the counter-ion (Ainscough et al., 1990; Li, Chen et al., 1993; Li, Wei et al., 1993). The only structures reported for iron(II) complexes of saccharin are those of the parent compound, [Fe(sac)2(H2O)4]·2H2O (Haider et al., 1983), and of the phen complex [Fe(phen)3](sac)2·4H2O (Li, Wei et al., 1993?). In the present work, we report the structure of another tris(1,10-phenanthroline)iron(II) complex, (I), with two saccharinate anions and one free saccharin molecule present, as well as six waters of crystallization. The compound has been confirmed as diamagnetic iron(II) (d6 low spin) by magnetic measurements, which clearly eliminates the alternative possibility of an iron(III) complex with three saccharinate anions. Such a d5 complex, if low spin, would be paramagnetic, with one unpaired electron present, while a high spin species would have five unpaired electrons. Low spin would be expected in any case, from the position of phen in the spectrochemical series. \sch

The structure of the title compound consists of slightly distorted octahedral [Fe(phen)3]2+ cations, with two saccharinate anions, a free saccharin molecule and six water molecules. The Fe—N distances (Table 1) are quite similar within each of the bidentate phen ligands, although the bonds are slightly longer to N3 and N4 than to the other four N atoms; the average Fe—N bond length is 1.966 Å. This compares well, for example, with the mean distance of 1.97 Å in l-[Fe(phen)3]bis[Sb(III)d-tartrate]·8H2O (Zalkin et al., 1973), 1.973 Å in [Fe(phen)3]I2·2H2O (Johansson et al., 1978) and 1.980 Å in [Fe(phen)3](sac)2·4H2O (Li, Wei et al., 1993?). The central Fe in (I) is very close to co-planarity with the four surrounding N atoms; the largest deviation is 0.014 (1) Å from the plane defined by N2, N3, N4 and N6. This compares with more significant deviations of 0.06, 0.03 and 0.008 Å in the structure of [Fe(phen)3](sac)2·4H2O (Li, Wei et al., 1993?).

The hydrogen-bonding geometry of (I) is shown in Table 2 and displayed in Fig. 2. There is a strong, essentially linear, hydrogen bond between H8 (on N8) in the saccharin molecule to O11 of a water molecule, with a distance of 1.70 (5) Å and a bond angle at H of 174 (4)°. The carbonyl oxygen O7 in one of the saccharinate anions appears to form linear hydrogen bonds with both H4W and H9W on adjacent water molecules, with distances and angles shown in Table 2. There is also a linear hydrogen bond between O3 on S1 in the second saccharinate anion and H11W (see Table 2). A shorter contact between the carbonyl oxygen O1 and H7W in this ion is also found at 1.853 (13) Å, but at a slightly less favourable angle of 164 (4)°. Other weaker hydrogen bonds between either the free saccharin molecule or a saccharinate anion and a water molecule are tabulated in Table 2, as well as hydrogen bonds between water molecules.

The overall hydrogen-bond scheme can be described as a three-dimensional network formed by the saccharinate anions, the free saccharin molecule and the water molecules. This network, shown in Fig. 3, leaves channels along the b axis where the cations reside.

Experimental top

Compound (I) was prepared by adding a warm solution of 1,10-phenanthroline (0.4488 g, 2.46 mmol) in water (50 ml), with stirring, to a warm clear solution of [Fe(sac)24H2O]·2H2O (0.4386 g, 0.83 mmol) in water (30 ml). A deep red solution formed; it was stirred for some time, and then left to stand. Fine red crystals formed after four weeks. These were separated, washed with 10 ml of cold distilled water and dried in air at room temperature. Elemental analyses, performed by the microanalytical services of the Department of Chemistry, University of Durham both before and after the crystal structure determination, indicated an average composition of [Fe(phen)3](sac)2.sacH·3H2O; found: C 57.18, H 3.72, N 10.66%; calculated for C57H43FeN9O12S3: C 57.15, H 3.62, N 10.52%. It is therefore probable that other material is present containing less water of crystallization than found in the crystals whose X-ray structure was determined in this work. Magnetic measurements were performed on a Johnson-Matthey-Evans magnetic susceptibility balance; the complex was shown to be diamagnetic.

Refinement top

All water H atoms and the amino H atom on the free saccharin molecule were refined. Other H atoms were treated as riding (C—H = 0.93 Å). Query.

Computing details top

Data collection: SMART-NT (Bruker, 1998); cell refinement: SMART-NT; data reduction: SAINT-NT (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL-NT (Bruker, 1998).

Figures top
[Figure 1] Fig. 1. The ORTEP (Johnson, 1965) drawing of the [Fe(C12H8N2)3]+ cation of (I) showing 70% probability displacement ellipsoids. H atoms have been omitted for clarity.
[Figure 2] Fig. 2. The hydrogen-bonding scheme of (I). Atom types are represented as follows: N regular dot pattern, O shaded bottom left to top right, S cross-hatched, C shaded and H small open circles.
[Figure 3] Fig. 3. The packing diagram for (I) showing the three-dimensional network formed via hydrogen bonding by the anions, the free saccharin and the water molecules. Only the Fe centres (shaded top left to bottom right) from the cations are shown for clarity. Other atoms are represented as in Fig. 2.
tris(1,10-phenanthroline-N,N')iron(II) bis[1,2-benzisothiazol-3(2H)-onate 1,1-dioxide] 1,2-benzisothiazol-3(2H)-one 1,1-dioxide hexahydrate top
Crystal data top
[Fe(C12H8N2)3](C7H4NO3S)2·C7H5NO3S·6H2OF(000) = 2592
Mr = 1252.08Dx = 1.572 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 16.113 (4) ÅCell parameters from 869 reflections
b = 19.079 (5) Åθ = 10.2–21.5°
c = 17.227 (4) ŵ = 0.49 mm1
β = 92.873 (5)°T = 120 K
V = 5289 (2) Å3Rectangular plate, red
Z = 40.48 × 0.19 × 0.10 mm
Data collection top
Bruker SMART-CCD
diffractometer
14753 independent reflections
Radiation source: fine-focus sealed tube7374 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.115
ω scansθmax = 30.5°, θmin = 1.6°
Absorption correction: integration
(SHELXTL-NT; Bruker, 1998)
h = 2220
Tmin = 0.830, Tmax = 0.954k = 2626
47439 measured reflectionsl = 2424
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.056Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.145H atoms treated by a mixture of independent and constrained refinement
S = 0.99 w = 1/[σ2(Fo2) + (0.0583P)2 + 0.6223P]
where P = (Fo2 + 2Fc2)/3
14753 reflections(Δ/σ)max = 0.001
812 parametersΔρmax = 0.52 e Å3
18 restraintsΔρmin = 0.70 e Å3
Crystal data top
[Fe(C12H8N2)3](C7H4NO3S)2·C7H5NO3S·6H2OV = 5289 (2) Å3
Mr = 1252.08Z = 4
Monoclinic, P21/nMo Kα radiation
a = 16.113 (4) ŵ = 0.49 mm1
b = 19.079 (5) ÅT = 120 K
c = 17.227 (4) Å0.48 × 0.19 × 0.10 mm
β = 92.873 (5)°
Data collection top
Bruker SMART-CCD
diffractometer
14753 independent reflections
Absorption correction: integration
(SHELXTL-NT; Bruker, 1998)
7374 reflections with I > 2σ(I)
Tmin = 0.830, Tmax = 0.954Rint = 0.115
47439 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.05618 restraints
wR(F2) = 0.145H atoms treated by a mixture of independent and constrained refinement
S = 0.99Δρmax = 0.52 e Å3
14753 reflectionsΔρmin = 0.70 e Å3
812 parameters
Special details top

Experimental. The detector was positioned at 2θ = -26° at a distance of 45 mm from the crystal. Data collection was carried out using ω scans, 0.3° wide 10 secs frames, starting at 3 different ϕ positions in order to cover a hemisphere.

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
xyzUiso*/Ueq
Fe10.52163 (3)0.24308 (2)0.54286 (2)0.01375 (11)
N10.48774 (16)0.30757 (14)0.45813 (14)0.0159 (6)
C10.4952 (2)0.30126 (18)0.38174 (18)0.0184 (7)
H1A0.51840.26050.36270.022*
C20.4696 (2)0.35343 (19)0.32946 (19)0.0206 (8)
H2A0.47670.34720.27670.025*
C30.4342 (2)0.41348 (19)0.35485 (19)0.0210 (8)
H3A0.41630.44800.31980.025*
C40.4252 (2)0.42246 (18)0.43517 (18)0.0175 (7)
C50.3899 (2)0.48258 (19)0.4694 (2)0.0243 (8)
H5B0.36870.51840.43760.029*
C60.3865 (2)0.48868 (19)0.5476 (2)0.0237 (8)
H6A0.36160.52790.56860.028*
C70.4206 (2)0.43578 (18)0.59782 (18)0.0188 (7)
C80.4250 (2)0.44084 (19)0.67953 (19)0.0226 (8)
H8A0.40250.47930.70420.027*
C90.4629 (2)0.38812 (18)0.72189 (19)0.0219 (8)
H9A0.46770.39120.77580.026*
C100.4941 (2)0.33032 (18)0.68477 (18)0.0179 (7)
H10A0.51960.29530.71500.021*
N20.48953 (16)0.32216 (14)0.60776 (14)0.0157 (6)
C110.45404 (19)0.37585 (17)0.56550 (18)0.0154 (7)
C120.45482 (19)0.36833 (17)0.48390 (18)0.0163 (7)
N30.40924 (16)0.20186 (14)0.54246 (14)0.0151 (6)
C130.3414 (2)0.22384 (18)0.57630 (18)0.0192 (7)
H13A0.34400.26540.60440.023*
C140.2667 (2)0.1869 (2)0.57116 (19)0.0236 (8)
H14A0.22080.20410.59560.028*
C150.2607 (2)0.12618 (18)0.53080 (19)0.0206 (8)
H15A0.21080.10170.52720.025*
C160.3307 (2)0.10048 (18)0.49437 (18)0.0175 (7)
C170.3315 (2)0.03785 (18)0.44892 (19)0.0226 (8)
H17A0.28360.01070.44350.027*
C180.4002 (2)0.01743 (19)0.41390 (19)0.0230 (8)
H18A0.39900.02370.38480.028*
C190.4753 (2)0.05772 (17)0.42043 (18)0.0176 (7)
C200.5487 (2)0.04083 (19)0.38436 (19)0.0216 (8)
H20A0.55160.00060.35420.026*
C210.6160 (2)0.08420 (18)0.39404 (19)0.0223 (8)
H21A0.66510.07340.37040.027*
C220.6113 (2)0.14416 (18)0.43894 (18)0.0180 (7)
H22A0.65810.17250.44510.022*
N40.54250 (16)0.16316 (14)0.47379 (14)0.0148 (6)
C230.47567 (19)0.11937 (17)0.46471 (17)0.0147 (7)
C240.40288 (19)0.14099 (17)0.50169 (17)0.0145 (7)
N50.56186 (16)0.18701 (14)0.63259 (14)0.0135 (6)
C250.5201 (2)0.14570 (17)0.67989 (18)0.0188 (7)
H25A0.46310.14060.67080.023*
C260.5592 (2)0.10987 (17)0.74241 (18)0.0189 (7)
H26A0.52800.08210.77430.023*
C270.6427 (2)0.11561 (18)0.75665 (18)0.0196 (7)
H27A0.66880.09230.79850.024*
C280.6889 (2)0.15707 (18)0.70748 (18)0.0182 (7)
C290.7770 (2)0.16672 (18)0.71560 (19)0.0222 (8)
H29A0.80710.14370.75530.027*
C300.8169 (2)0.20836 (18)0.66702 (19)0.0211 (8)
H30A0.87450.21220.67280.025*
C310.77325 (19)0.24695 (18)0.60652 (18)0.0174 (7)
C320.8105 (2)0.29269 (18)0.55613 (19)0.0215 (8)
H32A0.86780.29930.55890.026*
C330.7611 (2)0.32784 (19)0.50230 (19)0.0221 (8)
H33A0.78480.35960.46890.026*
C340.6759 (2)0.31651 (18)0.49703 (18)0.0198 (7)
H34A0.64390.34100.45960.024*
N60.63808 (16)0.27221 (14)0.54319 (14)0.0152 (6)
C350.68753 (19)0.23848 (17)0.59791 (17)0.0147 (7)
C360.64497 (19)0.19251 (17)0.64705 (17)0.0143 (7)
N70.29673 (18)0.00231 (16)0.84201 (16)0.0242 (7)
C370.3573 (2)0.01256 (18)0.89624 (19)0.0193 (7)
O10.37995 (15)0.02634 (12)0.95100 (13)0.0235 (5)
C380.3956 (2)0.08361 (18)0.88669 (18)0.0165 (7)
C390.4582 (2)0.11577 (19)0.93168 (19)0.0200 (7)
H39A0.48620.09200.97220.024*
C400.4778 (2)0.18382 (19)0.91465 (19)0.0243 (8)
H40A0.52010.20600.94390.029*
C410.4361 (2)0.22044 (19)0.85501 (19)0.0238 (8)
H41A0.44990.26690.84580.029*
C420.3739 (2)0.18806 (19)0.80888 (19)0.0214 (8)
H42A0.34590.21170.76830.026*
C430.3559 (2)0.12010 (19)0.82593 (18)0.0193 (7)
S10.28134 (5)0.06220 (5)0.78363 (5)0.0230 (2)
O20.30215 (16)0.04516 (14)0.70548 (13)0.0310 (6)
O30.19901 (15)0.09069 (14)0.79033 (15)0.0308 (6)
N80.74313 (19)0.36323 (16)0.79381 (16)0.0218 (7)
H8N0.701 (3)0.339 (2)0.816 (3)0.057 (14)*
C440.8238 (2)0.34047 (18)0.80033 (18)0.0190 (7)
O40.84977 (14)0.29645 (13)0.84588 (13)0.0226 (5)
C450.8730 (2)0.37726 (17)0.74232 (18)0.0184 (7)
C460.9562 (2)0.36890 (19)0.7294 (2)0.0230 (8)
H46A0.98900.33820.75950.028*
C470.9895 (2)0.40754 (19)0.6703 (2)0.0245 (8)
H47A1.04570.40320.66110.029*
C480.9400 (2)0.45258 (18)0.62465 (19)0.0228 (8)
H48A0.96360.47780.58520.027*
C490.8565 (2)0.46074 (18)0.63656 (19)0.0215 (8)
H49A0.82310.49060.60580.026*
C500.8250 (2)0.42274 (17)0.69595 (18)0.0169 (7)
S20.72285 (5)0.42219 (5)0.72614 (5)0.01966 (19)
O50.70229 (15)0.48753 (13)0.75978 (14)0.0274 (6)
O60.66567 (15)0.39484 (13)0.66736 (13)0.0265 (6)
N90.42304 (17)0.33972 (15)0.99403 (16)0.0219 (6)
C510.4967 (2)0.36627 (18)0.97701 (19)0.0191 (7)
O70.56490 (14)0.33866 (13)0.99665 (13)0.0231 (6)
C520.4920 (2)0.43249 (18)0.93115 (18)0.0175 (7)
C530.5557 (2)0.47344 (18)0.90557 (18)0.0208 (8)
H53A0.61090.46060.91530.025*
C540.5353 (2)0.53413 (19)0.86511 (19)0.0250 (8)
H54A0.57740.56270.84780.030*
C550.4530 (2)0.55290 (19)0.84999 (19)0.0259 (8)
H55A0.44080.59410.82290.031*
C560.3886 (2)0.51171 (18)0.87422 (18)0.0213 (8)
H56A0.33330.52360.86320.026*
C570.4105 (2)0.45236 (18)0.91538 (18)0.0177 (7)
S30.34868 (5)0.38661 (5)0.95553 (5)0.0209 (2)
O80.29725 (14)0.41467 (13)1.01375 (14)0.0270 (6)
O90.30438 (15)0.34905 (13)0.89333 (14)0.0292 (6)
O100.73902 (18)0.18541 (15)0.90609 (16)0.0356 (7)
H1W0.779 (3)0.218 (2)0.908 (2)0.093 (14)*
H2W0.731 (3)0.174 (3)0.9557 (9)0.093 (14)*
O110.63066 (16)0.29071 (14)0.86289 (15)0.0297 (6)
H3W0.658 (3)0.2500 (14)0.872 (2)0.072 (12)*
H4W0.612 (3)0.305 (2)0.9085 (12)0.072 (12)*
O120.7536 (2)0.17201 (19)0.23007 (18)0.0532 (9)
H5W0.750 (4)0.1333 (16)0.200 (2)0.119 (18)*
H6W0.747 (4)0.158 (3)0.2792 (11)0.119 (18)*
O130.3036 (2)0.15423 (15)0.94486 (19)0.0460 (8)
H7W0.321 (2)0.1095 (7)0.952 (3)0.070 (12)*
H8W0.3500 (14)0.1795 (16)0.939 (3)0.070 (12)*
O140.0632 (2)0.26506 (15)0.60654 (16)0.0430 (8)
H9W0.063 (4)0.2295 (15)0.5721 (18)0.094 (15)*
H10W0.073 (4)0.245 (2)0.6537 (11)0.094 (15)*
O150.13016 (17)0.22951 (16)0.75558 (16)0.0372 (7)
H11W0.154 (2)0.1878 (8)0.767 (3)0.056 (10)*
H12W0.1712 (15)0.2614 (13)0.759 (3)0.056 (10)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Fe10.0119 (2)0.0182 (3)0.0109 (2)0.00072 (19)0.00246 (16)0.0003 (2)
N10.0118 (14)0.0219 (16)0.0137 (13)0.0011 (12)0.0014 (10)0.0022 (12)
C10.0146 (18)0.026 (2)0.0137 (16)0.0027 (14)0.0041 (13)0.0037 (15)
C20.0192 (19)0.030 (2)0.0119 (16)0.0045 (15)0.0051 (13)0.0039 (15)
C30.0170 (18)0.027 (2)0.0179 (17)0.0020 (15)0.0066 (13)0.0070 (15)
C40.0127 (17)0.0223 (19)0.0169 (16)0.0020 (14)0.0052 (13)0.0010 (14)
C50.021 (2)0.026 (2)0.0256 (19)0.0021 (15)0.0083 (14)0.0068 (16)
C60.024 (2)0.020 (2)0.0269 (19)0.0054 (15)0.0016 (15)0.0006 (15)
C70.0154 (18)0.0223 (19)0.0185 (17)0.0021 (14)0.0013 (13)0.0016 (15)
C80.0220 (19)0.024 (2)0.0222 (18)0.0004 (15)0.0039 (14)0.0073 (15)
C90.027 (2)0.024 (2)0.0139 (16)0.0035 (16)0.0005 (14)0.0043 (15)
C100.0191 (18)0.0214 (19)0.0127 (16)0.0006 (14)0.0026 (13)0.0008 (14)
N20.0114 (14)0.0211 (16)0.0144 (13)0.0041 (11)0.0024 (10)0.0014 (12)
C110.0114 (17)0.0181 (18)0.0163 (16)0.0038 (13)0.0023 (12)0.0014 (14)
C120.0110 (17)0.0209 (19)0.0166 (16)0.0062 (13)0.0028 (12)0.0005 (14)
N30.0151 (15)0.0175 (15)0.0123 (13)0.0035 (11)0.0036 (11)0.0019 (11)
C130.0172 (18)0.024 (2)0.0164 (16)0.0037 (14)0.0019 (13)0.0008 (14)
C140.0179 (19)0.031 (2)0.0218 (18)0.0032 (16)0.0026 (14)0.0027 (16)
C150.0134 (18)0.028 (2)0.0204 (18)0.0039 (15)0.0027 (13)0.0072 (15)
C160.0151 (17)0.0211 (19)0.0157 (16)0.0020 (14)0.0039 (13)0.0067 (14)
C170.0208 (19)0.023 (2)0.0236 (18)0.0067 (15)0.0046 (14)0.0012 (15)
C180.027 (2)0.0204 (19)0.0214 (18)0.0032 (15)0.0044 (15)0.0038 (15)
C190.0195 (18)0.0202 (19)0.0125 (16)0.0002 (14)0.0048 (13)0.0007 (14)
C200.024 (2)0.023 (2)0.0185 (17)0.0009 (15)0.0016 (14)0.0054 (15)
C210.0182 (19)0.029 (2)0.0196 (17)0.0058 (15)0.0014 (14)0.0015 (16)
C220.0110 (17)0.0230 (19)0.0196 (17)0.0010 (14)0.0033 (13)0.0019 (15)
N40.0119 (14)0.0199 (15)0.0123 (13)0.0022 (11)0.0026 (10)0.0033 (11)
C230.0144 (17)0.0177 (17)0.0114 (15)0.0012 (14)0.0041 (12)0.0027 (13)
C240.0144 (17)0.0179 (18)0.0108 (15)0.0004 (13)0.0037 (12)0.0039 (13)
N50.0147 (14)0.0137 (14)0.0120 (13)0.0010 (11)0.0006 (10)0.0025 (11)
C250.0199 (19)0.0182 (18)0.0179 (17)0.0004 (14)0.0014 (13)0.0009 (14)
C260.024 (2)0.0171 (18)0.0158 (16)0.0012 (14)0.0016 (14)0.0003 (14)
C270.0228 (19)0.0209 (19)0.0146 (16)0.0035 (15)0.0044 (13)0.0050 (14)
C280.0185 (18)0.0209 (19)0.0144 (16)0.0033 (14)0.0055 (13)0.0027 (14)
C290.0186 (19)0.026 (2)0.0206 (18)0.0046 (15)0.0087 (14)0.0012 (16)
C300.0137 (18)0.024 (2)0.0246 (19)0.0005 (14)0.0045 (14)0.0050 (16)
C310.0131 (17)0.0196 (18)0.0190 (16)0.0019 (14)0.0041 (12)0.0067 (15)
C320.0151 (18)0.028 (2)0.0214 (18)0.0063 (15)0.0006 (14)0.0062 (16)
C330.0202 (19)0.029 (2)0.0175 (17)0.0082 (15)0.0026 (14)0.0016 (15)
C340.0218 (19)0.0236 (19)0.0138 (16)0.0027 (15)0.0021 (13)0.0012 (14)
N60.0157 (15)0.0180 (15)0.0118 (13)0.0015 (11)0.0017 (11)0.0007 (11)
C350.0155 (17)0.0164 (17)0.0119 (15)0.0013 (13)0.0009 (12)0.0031 (13)
C360.0133 (17)0.0159 (17)0.0133 (15)0.0001 (13)0.0018 (12)0.0042 (13)
N70.0201 (17)0.0269 (17)0.0253 (16)0.0046 (13)0.0016 (12)0.0018 (13)
C370.0156 (18)0.024 (2)0.0184 (17)0.0004 (14)0.0038 (13)0.0047 (15)
O10.0242 (14)0.0240 (14)0.0221 (13)0.0001 (11)0.0011 (10)0.0061 (11)
C380.0151 (17)0.0202 (18)0.0143 (16)0.0029 (14)0.0033 (13)0.0002 (14)
C390.0162 (18)0.029 (2)0.0142 (16)0.0008 (15)0.0003 (13)0.0043 (15)
C400.026 (2)0.029 (2)0.0184 (18)0.0041 (16)0.0015 (15)0.0050 (16)
C410.027 (2)0.022 (2)0.0225 (18)0.0002 (16)0.0060 (15)0.0021 (15)
C420.0198 (19)0.028 (2)0.0167 (17)0.0028 (15)0.0017 (14)0.0032 (15)
C430.0152 (18)0.028 (2)0.0143 (16)0.0064 (15)0.0001 (13)0.0013 (15)
S10.0174 (5)0.0303 (5)0.0207 (4)0.0009 (4)0.0037 (3)0.0013 (4)
O20.0321 (15)0.0440 (17)0.0163 (12)0.0030 (13)0.0035 (11)0.0062 (12)
O30.0138 (13)0.0419 (17)0.0361 (15)0.0017 (11)0.0036 (11)0.0013 (13)
N80.0166 (16)0.0294 (18)0.0193 (15)0.0018 (13)0.0003 (12)0.0074 (13)
C440.0201 (19)0.0222 (19)0.0144 (16)0.0021 (15)0.0009 (13)0.0005 (15)
O40.0220 (14)0.0286 (15)0.0166 (12)0.0018 (11)0.0040 (10)0.0020 (11)
C450.0220 (19)0.0198 (19)0.0131 (16)0.0016 (14)0.0009 (13)0.0022 (14)
C460.0193 (19)0.026 (2)0.0233 (18)0.0008 (15)0.0003 (14)0.0024 (16)
C470.0201 (19)0.027 (2)0.0273 (19)0.0020 (15)0.0047 (15)0.0048 (16)
C480.031 (2)0.021 (2)0.0175 (17)0.0070 (16)0.0072 (15)0.0057 (15)
C490.028 (2)0.0199 (19)0.0163 (17)0.0027 (15)0.0034 (14)0.0022 (14)
C500.0163 (18)0.0202 (19)0.0138 (16)0.0015 (14)0.0041 (13)0.0058 (14)
S20.0165 (4)0.0248 (5)0.0173 (4)0.0011 (4)0.0032 (3)0.0025 (4)
O50.0256 (14)0.0275 (15)0.0290 (14)0.0049 (11)0.0005 (11)0.0008 (11)
O60.0217 (14)0.0338 (15)0.0229 (13)0.0055 (11)0.0098 (10)0.0041 (11)
N90.0170 (16)0.0228 (17)0.0257 (16)0.0021 (12)0.0007 (12)0.0015 (13)
C510.0177 (19)0.0224 (19)0.0171 (17)0.0009 (15)0.0001 (13)0.0056 (14)
O70.0163 (13)0.0295 (15)0.0231 (13)0.0038 (10)0.0033 (10)0.0010 (11)
C520.0153 (17)0.0229 (19)0.0140 (16)0.0013 (14)0.0031 (12)0.0049 (14)
C530.0161 (18)0.027 (2)0.0189 (17)0.0020 (15)0.0042 (13)0.0069 (15)
C540.030 (2)0.028 (2)0.0175 (17)0.0056 (17)0.0032 (15)0.0028 (16)
C550.036 (2)0.026 (2)0.0148 (17)0.0065 (17)0.0046 (15)0.0017 (15)
C560.0196 (19)0.028 (2)0.0161 (17)0.0058 (15)0.0042 (13)0.0032 (15)
C570.0168 (18)0.0237 (19)0.0125 (16)0.0011 (14)0.0016 (13)0.0045 (14)
S30.0135 (4)0.0238 (5)0.0249 (4)0.0012 (4)0.0018 (3)0.0032 (4)
O80.0185 (14)0.0334 (15)0.0294 (14)0.0049 (11)0.0038 (10)0.0024 (12)
O90.0193 (14)0.0354 (16)0.0322 (14)0.0026 (11)0.0071 (11)0.0078 (12)
O100.0377 (18)0.0348 (17)0.0342 (15)0.0002 (14)0.0005 (13)0.0025 (13)
O110.0264 (15)0.0357 (17)0.0277 (14)0.0008 (12)0.0067 (11)0.0041 (12)
O120.045 (2)0.072 (2)0.0406 (19)0.0143 (18)0.0118 (16)0.0170 (17)
O130.059 (2)0.0276 (17)0.0519 (19)0.0118 (15)0.0072 (17)0.0028 (15)
O140.060 (2)0.0340 (17)0.0343 (17)0.0073 (15)0.0074 (15)0.0071 (13)
O150.0290 (16)0.0480 (19)0.0346 (16)0.0001 (13)0.0015 (12)0.0035 (15)
Geometric parameters (Å, º) top
Fe1—N11.965 (3)C32—H32A0.9300
Fe1—N21.963 (3)C33—C341.388 (5)
Fe1—N31.974 (3)C33—H33A0.9300
Fe1—N41.973 (3)C34—N61.329 (4)
Fe1—N51.963 (3)C34—H34A0.9300
Fe1—N61.957 (3)N6—C351.365 (4)
N1—C11.333 (4)C35—C361.419 (4)
N1—C121.359 (4)N7—C371.347 (4)
C1—C21.391 (5)N7—S11.601 (3)
C1—H1A0.9300C37—O11.241 (4)
C2—C31.362 (5)C37—C381.502 (5)
C2—H2A0.9300C38—C391.385 (5)
C3—C41.409 (4)C38—C431.386 (4)
C3—H3A0.9300C39—C401.371 (5)
C4—C121.400 (4)C39—H39A0.9300
C4—C51.421 (5)C40—C411.388 (5)
C5—C61.356 (5)C40—H40A0.9300
C5—H5B0.9300C41—C421.392 (5)
C6—C71.422 (5)C41—H41A0.9300
C6—H6A0.9300C42—C431.364 (5)
C7—C111.392 (5)C42—H42A0.9300
C7—C81.409 (5)C43—S11.763 (4)
C8—C91.369 (5)S1—O21.441 (2)
C8—H8A0.9300S1—O31.444 (3)
C9—C101.382 (5)N8—C441.370 (4)
C9—H9A0.9300N8—S21.641 (3)
C10—N21.334 (4)N8—H8N0.92 (5)
C10—H10A0.9300C44—O41.210 (4)
N2—C111.366 (4)C44—C451.483 (5)
C11—C121.414 (4)C45—C461.378 (5)
N3—C131.332 (4)C45—C501.388 (5)
N3—C241.359 (4)C46—C471.387 (5)
C13—C141.394 (5)C46—H46A0.9300
C13—H13A0.9300C47—C481.390 (5)
C14—C151.352 (5)C47—H47A0.9300
C14—H14A0.9300C48—C491.380 (5)
C15—C161.406 (5)C48—H48A0.9300
C15—H15A0.9300C49—C501.372 (5)
C16—C241.397 (4)C49—H49A0.9300
C16—C171.429 (5)C50—S21.751 (3)
C17—C181.345 (5)S2—O51.421 (3)
C17—H17A0.9300S2—O61.433 (2)
C18—C191.433 (5)N9—C511.336 (4)
C18—H18A0.9300N9—S31.611 (3)
C19—C201.401 (5)C51—O71.250 (4)
C19—C231.402 (4)C51—C521.490 (5)
C20—C211.368 (5)C52—C571.379 (4)
C20—H20A0.9300C52—C531.381 (5)
C21—C221.385 (5)C53—C541.383 (5)
C21—H21A0.9300C53—H53A0.9300
C22—N41.337 (4)C54—C551.385 (5)
C22—H22A0.9300C54—H54A0.9300
N4—C231.366 (4)C55—C561.383 (5)
C23—C241.423 (4)C55—H55A0.9300
N5—C251.339 (4)C56—C571.373 (5)
N5—C361.354 (4)C56—H56A0.9300
C25—C261.399 (5)C57—S31.765 (3)
C25—H25A0.9300S3—O81.436 (2)
C26—C271.360 (5)S3—O91.447 (2)
C26—H26A0.9300O10—H1W0.900 (5)
C27—C281.400 (5)O10—H2W0.900 (5)
C27—H27A0.9300O11—H3W0.899 (5)
C28—C361.403 (4)O11—H4W0.898 (5)
C28—C291.431 (5)O12—H5W0.900 (5)
C29—C301.342 (5)O12—H6W0.898 (5)
C29—H29A0.9300O13—H7W0.902 (5)
C30—C311.432 (5)O13—H8W0.902 (5)
C30—H30A0.9300O14—H9W0.901 (5)
C31—C321.389 (5)O14—H10W0.900 (5)
C31—C351.391 (4)O15—H11W0.899 (5)
C32—C331.367 (5)O15—H12W0.898 (5)
N1—Fe1—N282.55 (11)C29—C30—C31121.6 (3)
N1—Fe1—N391.50 (11)C29—C30—H30A119.2
N1—Fe1—N494.89 (11)C31—C30—H30A119.2
N1—Fe1—N5173.96 (11)C32—C31—C35117.7 (3)
N1—Fe1—N693.15 (11)C32—C31—C30124.5 (3)
N2—Fe1—N392.31 (11)C35—C31—C30117.9 (3)
N2—Fe1—N4174.42 (11)C33—C32—C31118.5 (3)
N2—Fe1—N593.23 (11)C33—C32—H32A120.8
N2—Fe1—N693.44 (11)C31—C32—H32A120.8
N3—Fe1—N482.77 (11)C32—C33—C34120.6 (3)
N3—Fe1—N593.00 (11)C32—C33—H33A119.7
N3—Fe1—N6173.03 (11)C34—C33—H33A119.7
N4—Fe1—N589.67 (10)N6—C34—C33122.8 (3)
N4—Fe1—N691.66 (11)N6—C34—H34A118.6
N5—Fe1—N682.75 (11)C33—C34—H34A118.6
C1—N1—C12117.1 (3)C34—N6—C35116.3 (3)
C1—N1—Fe1129.9 (2)C34—N6—Fe1130.3 (2)
C12—N1—Fe1113.0 (2)C35—N6—Fe1113.2 (2)
N1—C1—C2122.4 (3)N6—C35—C31124.1 (3)
N1—C1—H1A118.8N6—C35—C36114.9 (3)
C2—C1—H1A118.8C31—C35—C36121.0 (3)
C3—C2—C1120.6 (3)N5—C36—C28123.8 (3)
C3—C2—H2A119.7N5—C36—C35116.2 (3)
C1—C2—H2A119.7C28—C36—C35120.0 (3)
C2—C3—C4118.9 (3)C37—N7—S1111.0 (2)
C2—C3—H3A120.5O1—C37—N7125.2 (3)
C4—C3—H3A120.5O1—C37—C38121.1 (3)
C12—C4—C3116.7 (3)N7—C37—C38113.7 (3)
C12—C4—C5118.6 (3)C39—C38—C43119.7 (3)
C3—C4—C5124.7 (3)C39—C38—C37129.1 (3)
C6—C5—C4121.2 (3)C43—C38—C37111.1 (3)
C6—C5—H5B119.4C40—C39—C38117.9 (3)
C4—C5—H5B119.4C40—C39—H39A121.0
C5—C6—C7120.7 (3)C38—C39—H39A121.0
C5—C6—H6A119.7C39—C40—C41121.8 (3)
C7—C6—H6A119.7C39—C40—H40A119.1
C11—C7—C8117.1 (3)C41—C40—H40A119.1
C11—C7—C6119.0 (3)C40—C41—C42120.5 (3)
C8—C7—C6123.9 (3)C40—C41—H41A119.8
C9—C8—C7118.7 (3)C42—C41—H41A119.8
C9—C8—H8A120.6C43—C42—C41117.0 (3)
C7—C8—H8A120.6C43—C42—H42A121.5
C8—C9—C10120.2 (3)C41—C42—H42A121.5
C8—C9—H9A119.9C42—C43—C38123.0 (3)
C10—C9—H9A119.9C42—C43—S1130.9 (3)
N2—C10—C9123.4 (3)C38—C43—S1106.0 (3)
N2—C10—H10A118.3O2—S1—O3114.67 (15)
C9—C10—H10A118.3O2—S1—N7112.18 (16)
C10—N2—C11116.3 (3)O3—S1—N7110.69 (16)
C10—N2—Fe1130.8 (2)O2—S1—C43109.99 (16)
C11—N2—Fe1112.8 (2)O3—S1—C43109.95 (16)
N2—C11—C7124.3 (3)N7—S1—C4398.12 (15)
N2—C11—C12115.4 (3)C44—N8—S2115.5 (2)
C7—C11—C12120.3 (3)C44—N8—H8N122 (3)
N1—C12—C4124.1 (3)S2—N8—H8N121 (3)
N1—C12—C11115.8 (3)O4—C44—N8124.7 (3)
C4—C12—C11120.1 (3)O4—C44—C45125.9 (3)
C13—N3—C24116.9 (3)N8—C44—C45109.4 (3)
C13—N3—Fe1130.2 (2)C46—C45—C50119.8 (3)
C24—N3—Fe1112.8 (2)C46—C45—C44127.6 (3)
N3—C13—C14122.5 (3)C50—C45—C44112.5 (3)
N3—C13—H13A118.7C45—C46—C47118.2 (3)
C14—C13—H13A118.7C45—C46—H46A120.9
C15—C14—C13120.3 (3)C47—C46—H46A120.9
C15—C14—H14A119.8C46—C47—C48120.8 (3)
C13—C14—H14A119.8C46—C47—H47A119.6
C14—C15—C16119.3 (3)C48—C47—H47A119.6
C14—C15—H15A120.3C49—C48—C47121.5 (3)
C16—C15—H15A120.3C49—C48—H48A119.3
C24—C16—C15116.7 (3)C47—C48—H48A119.3
C24—C16—C17118.8 (3)C50—C49—C48116.8 (3)
C15—C16—C17124.4 (3)C50—C49—H49A121.6
C18—C17—C16121.2 (3)C48—C49—H49A121.6
C18—C17—H17A119.4C49—C50—C45122.9 (3)
C16—C17—H17A119.4C49—C50—S2127.8 (3)
C17—C18—C19121.4 (3)C45—C50—S2109.3 (2)
C17—C18—H18A119.3O5—S2—O6116.93 (15)
C19—C18—H18A119.3O5—S2—N8110.72 (15)
C20—C19—C23117.0 (3)O6—S2—N8110.52 (16)
C20—C19—C18124.7 (3)O5—S2—C50110.96 (16)
C23—C19—C18118.3 (3)O6—S2—C50111.91 (15)
C21—C20—C19119.3 (3)N8—S2—C5093.35 (16)
C21—C20—H20A120.4C51—N9—S3110.4 (2)
C19—C20—H20A120.4O7—C51—N9124.0 (3)
C20—C21—C22120.1 (3)O7—C51—C52121.4 (3)
C20—C21—H21A119.9N9—C51—C52114.6 (3)
C22—C21—H21A119.9C57—C52—C53119.8 (3)
N4—C22—C21123.0 (3)C57—C52—C51111.1 (3)
N4—C22—H22A118.5C53—C52—C51129.1 (3)
C21—C22—H22A118.5C52—C53—C54118.2 (3)
C22—N4—C23116.7 (3)C52—C53—H53A120.9
C22—N4—Fe1130.6 (2)C54—C53—H53A120.9
C23—N4—Fe1112.6 (2)C53—C54—C55120.8 (3)
N4—C23—C19123.9 (3)C53—C54—H54A119.6
N4—C23—C24115.7 (3)C55—C54—H54A119.6
C19—C23—C24120.4 (3)C56—C55—C54121.5 (3)
N3—C24—C16124.1 (3)C56—C55—H55A119.3
N3—C24—C23115.9 (3)C54—C55—H55A119.3
C16—C24—C23120.0 (3)C57—C56—C55116.5 (3)
C25—N5—C36117.1 (3)C57—C56—H56A121.7
C25—N5—Fe1130.1 (2)C55—C56—H56A121.7
C36—N5—Fe1112.8 (2)C56—C57—C52123.1 (3)
N5—C25—C26122.4 (3)C56—C57—S3130.7 (3)
N5—C25—H25A118.8C52—C57—S3106.1 (2)
C26—C25—H25A118.8O8—S3—O9114.92 (15)
C27—C26—C25120.2 (3)O8—S3—N9111.26 (15)
C27—C26—H26A119.9O9—S3—N9111.03 (16)
C25—C26—H26A119.9O8—S3—C57111.45 (16)
C26—C27—C28119.2 (3)O9—S3—C57109.21 (15)
C26—C27—H27A120.4N9—S3—C5797.64 (15)
C28—C27—H27A120.4H1W—O10—H2W106.1 (8)
C27—C28—C36117.2 (3)H3W—O11—H4W106.5 (8)
C27—C28—C29124.6 (3)H5W—O12—H6W106.5 (8)
C36—C28—C29118.1 (3)H7W—O13—H8W105.8 (8)
C30—C29—C28121.3 (3)H9W—O14—H10W106.0 (8)
C30—C29—H29A119.3H11W—O15—H12W106.6 (8)
C28—C29—H29A119.3
N6—Fe1—N1—C179.4 (3)Fe1—N5—C25—C26179.2 (2)
N2—Fe1—N1—C1172.5 (3)N5—C25—C26—C270.7 (5)
N5—Fe1—N1—C1126.5 (10)C25—C26—C27—C280.7 (5)
N4—Fe1—N1—C112.5 (3)C26—C27—C28—C362.0 (5)
N3—Fe1—N1—C195.4 (3)C26—C27—C28—C29179.2 (3)
N6—Fe1—N1—C1297.8 (2)C27—C28—C29—C30178.8 (3)
N2—Fe1—N1—C124.8 (2)C36—C28—C29—C300.0 (5)
N5—Fe1—N1—C1250.7 (11)C28—C29—C30—C312.2 (5)
N4—Fe1—N1—C12170.2 (2)C29—C30—C31—C32177.7 (3)
N3—Fe1—N1—C1287.4 (2)C29—C30—C31—C351.8 (5)
C12—N1—C1—C21.0 (4)C35—C31—C32—C331.4 (5)
Fe1—N1—C1—C2178.2 (2)C30—C31—C32—C33178.1 (3)
N1—C1—C2—C31.0 (5)C31—C32—C33—C341.7 (5)
C1—C2—C3—C41.0 (5)C32—C33—C34—N60.4 (5)
C2—C3—C4—C120.9 (5)C33—C34—N6—C351.0 (5)
C2—C3—C4—C5179.6 (3)C33—C34—N6—Fe1175.6 (2)
C12—C4—C5—C61.5 (5)N2—Fe1—N6—C3486.6 (3)
C3—C4—C5—C6177.2 (3)N5—Fe1—N6—C34179.4 (3)
C4—C5—C6—C71.9 (5)N1—Fe1—N6—C343.9 (3)
C5—C6—C7—C113.1 (5)N4—Fe1—N6—C3491.1 (3)
C5—C6—C7—C8175.1 (3)N3—Fe1—N6—C34127.9 (8)
C11—C7—C8—C91.4 (5)N2—Fe1—N6—C3596.7 (2)
C6—C7—C8—C9176.8 (3)N5—Fe1—N6—C353.9 (2)
C7—C8—C9—C101.8 (5)N1—Fe1—N6—C35179.4 (2)
C8—C9—C10—N20.0 (5)N4—Fe1—N6—C3585.6 (2)
C9—C10—N2—C112.1 (5)N3—Fe1—N6—C3548.8 (10)
C9—C10—N2—Fe1175.1 (2)C34—N6—C35—C311.2 (5)
N6—Fe1—N2—C1083.9 (3)Fe1—N6—C35—C31176.0 (2)
N5—Fe1—N2—C100.9 (3)C34—N6—C35—C36179.0 (3)
N1—Fe1—N2—C10176.6 (3)Fe1—N6—C35—C363.8 (3)
N4—Fe1—N2—C10120.3 (11)C32—C31—C35—N60.0 (5)
N3—Fe1—N2—C1092.2 (3)C30—C31—C35—N6179.6 (3)
N6—Fe1—N2—C1198.8 (2)C32—C31—C35—C36179.8 (3)
N5—Fe1—N2—C11178.3 (2)C30—C31—C35—C360.6 (5)
N1—Fe1—N2—C116.1 (2)C25—N5—C36—C280.8 (4)
N4—Fe1—N2—C1157.0 (12)Fe1—N5—C36—C28179.4 (3)
N3—Fe1—N2—C1185.1 (2)C25—N5—C36—C35177.9 (3)
C10—N2—C11—C72.4 (5)Fe1—N5—C36—C352.0 (3)
Fe1—N2—C11—C7175.3 (3)C27—C28—C36—N52.1 (5)
C10—N2—C11—C12175.9 (3)C29—C28—C36—N5179.0 (3)
Fe1—N2—C11—C126.4 (3)C27—C28—C36—C35176.4 (3)
C8—C7—C11—N20.7 (5)C29—C28—C36—C352.4 (5)
C6—C7—C11—N2179.0 (3)N6—C35—C36—N51.2 (4)
C8—C7—C11—C12177.5 (3)C31—C35—C36—N5178.6 (3)
C6—C7—C11—C120.7 (5)N6—C35—C36—C28177.5 (3)
C1—N1—C12—C43.1 (5)C31—C35—C36—C282.7 (5)
Fe1—N1—C12—C4179.3 (2)S1—N7—C37—O1176.7 (3)
C1—N1—C12—C11175.0 (3)S1—N7—C37—C381.6 (4)
Fe1—N1—C12—C112.7 (3)O1—C37—C38—C391.1 (5)
C3—C4—C12—N13.0 (5)N7—C37—C38—C39179.5 (3)
C5—C4—C12—N1178.2 (3)O1—C37—C38—C43174.8 (3)
C3—C4—C12—C11174.9 (3)N7—C37—C38—C433.6 (4)
C5—C4—C12—C113.9 (5)C43—C38—C39—C401.0 (5)
N2—C11—C12—N12.5 (4)C37—C38—C39—C40174.6 (3)
C7—C11—C12—N1179.1 (3)C38—C39—C40—C410.7 (5)
N2—C11—C12—C4175.7 (3)C39—C40—C41—C421.7 (5)
C7—C11—C12—C42.7 (5)C40—C41—C42—C430.8 (5)
N6—Fe1—N3—C13145.1 (8)C41—C42—C43—C380.9 (5)
N2—Fe1—N3—C130.4 (3)C41—C42—C43—S1178.5 (3)
N5—Fe1—N3—C1392.9 (3)C39—C38—C43—C421.9 (5)
N1—Fe1—N3—C1383.0 (3)C37—C38—C43—C42174.5 (3)
N4—Fe1—N3—C13177.8 (3)C39—C38—C43—S1179.9 (2)
N6—Fe1—N3—C2433.7 (10)C37—C38—C43—S13.6 (3)
N2—Fe1—N3—C24179.3 (2)C37—N7—S1—O2115.1 (2)
N5—Fe1—N3—C2485.9 (2)C37—N7—S1—O3115.4 (2)
N1—Fe1—N3—C2498.1 (2)C37—N7—S1—C430.5 (3)
N4—Fe1—N3—C243.4 (2)C42—C43—S1—O267.4 (4)
C24—N3—C13—C140.2 (5)C38—C43—S1—O2114.7 (2)
Fe1—N3—C13—C14178.6 (2)C42—C43—S1—O359.8 (4)
N3—C13—C14—C150.1 (5)C38—C43—S1—O3118.1 (2)
C13—C14—C15—C160.3 (5)C42—C43—S1—N7175.3 (3)
C14—C15—C16—C240.9 (5)C38—C43—S1—N72.5 (3)
C14—C15—C16—C17178.7 (3)S2—N8—C44—O4178.7 (3)
C24—C16—C17—C180.4 (5)S2—N8—C44—C450.4 (4)
C15—C16—C17—C18178.1 (3)O4—C44—C45—C460.3 (6)
C16—C17—C18—C190.3 (5)N8—C44—C45—C46179.3 (3)
C17—C18—C19—C20178.5 (3)O4—C44—C45—C50177.3 (3)
C17—C18—C19—C230.2 (5)N8—C44—C45—C501.7 (4)
C23—C19—C20—C210.3 (5)C50—C45—C46—C470.8 (5)
C18—C19—C20—C21178.9 (3)C44—C45—C46—C47178.3 (3)
C19—C20—C21—C220.2 (5)C45—C46—C47—C481.0 (5)
C20—C21—C22—N40.7 (5)C46—C47—C48—C490.3 (5)
C21—C22—N4—C231.4 (5)C47—C48—C49—C500.5 (5)
C21—C22—N4—Fe1177.5 (2)C48—C49—C50—C450.7 (5)
N6—Fe1—N4—C224.3 (3)C48—C49—C50—S2179.3 (3)
N2—Fe1—N4—C22151.5 (10)C46—C45—C50—C490.0 (5)
N5—Fe1—N4—C2287.1 (3)C44—C45—C50—C49177.8 (3)
N1—Fe1—N4—C2289.0 (3)C46—C45—C50—S2180.0 (3)
N3—Fe1—N4—C22179.9 (3)C44—C45—C50—S22.2 (3)
N6—Fe1—N4—C23171.9 (2)C44—N8—S2—O5113.2 (3)
N2—Fe1—N4—C2332.3 (12)C44—N8—S2—O6115.6 (3)
N5—Fe1—N4—C2389.2 (2)C44—N8—S2—C500.7 (3)
N1—Fe1—N4—C2394.8 (2)C49—C50—S2—O568.0 (3)
N3—Fe1—N4—C233.9 (2)C45—C50—S2—O5112.0 (2)
C22—N4—C23—C191.3 (4)C49—C50—S2—O664.6 (3)
Fe1—N4—C23—C19178.1 (2)C45—C50—S2—O6115.4 (2)
C22—N4—C23—C24179.4 (3)C49—C50—S2—N8178.3 (3)
Fe1—N4—C23—C243.8 (3)C45—C50—S2—N81.7 (3)
C20—C19—C23—N40.5 (5)S3—N9—C51—O7176.8 (3)
C18—C19—C23—N4178.3 (3)S3—N9—C51—C522.6 (4)
C20—C19—C23—C24178.5 (3)O7—C51—C52—C57179.1 (3)
C18—C19—C23—C240.2 (4)N9—C51—C52—C570.4 (4)
C13—N3—C24—C160.9 (4)O7—C51—C52—C531.8 (5)
Fe1—N3—C24—C16178.1 (2)N9—C51—C52—C53178.8 (3)
C13—N3—C24—C23178.7 (3)C57—C52—C53—C540.6 (5)
Fe1—N3—C24—C232.3 (3)C51—C52—C53—C54178.5 (3)
C15—C16—C24—N31.3 (5)C52—C53—C54—C550.7 (5)
C17—C16—C24—N3179.1 (3)C53—C54—C55—C560.4 (5)
C15—C16—C24—C23178.3 (3)C54—C55—C56—C571.4 (5)
C17—C16—C24—C230.5 (4)C55—C56—C57—C521.5 (5)
N4—C23—C24—N31.0 (4)C55—C56—C57—S3179.5 (3)
C19—C23—C24—N3179.2 (3)C53—C52—C57—C560.5 (5)
N4—C23—C24—C16178.6 (3)C51—C52—C57—C56179.7 (3)
C19—C23—C24—C160.4 (4)C53—C52—C57—S3178.9 (2)
N6—Fe1—N5—C25176.7 (3)C51—C52—C57—S31.8 (3)
N2—Fe1—N5—C2583.6 (3)C51—N9—S3—O8119.9 (2)
N1—Fe1—N5—C25129.2 (10)C51—N9—S3—O9110.8 (2)
N4—Fe1—N5—C2591.6 (3)C51—N9—S3—C573.3 (3)
N3—Fe1—N5—C258.9 (3)C56—C57—S3—O862.3 (3)
N6—Fe1—N5—C363.2 (2)C52—C57—S3—O8119.5 (2)
N2—Fe1—N5—C3696.3 (2)C56—C57—S3—O965.8 (3)
N1—Fe1—N5—C3650.7 (11)C52—C57—S3—O9112.5 (2)
N4—Fe1—N5—C3688.5 (2)C56—C57—S3—N9178.7 (3)
N3—Fe1—N5—C36171.3 (2)C52—C57—S3—N93.0 (2)
C36—N5—C25—C260.7 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N8—H8N···O110.92 (5)1.70 (5)2.614 (4)174 (4)
O10—H1W···O40.89 (4)2.19 (2)2.989 (4)148 (4)
O10—H2W···O13i0.90 (3)1.87 (3)2.756 (4)171 (5)
O11—H3W···O100.90 (3)1.87 (4)2.740 (4)161 (5)
O11—H4W···O70.90 (3)1.85 (3)2.741 (3)174 (4)
O12—H5W···N7ii0.90 (3)2.70 (2)3.547 (5)157 (5)
O12—H6W···O9iii0.90 (3)2.13 (4)2.917 (4)146 (5)
O13—H7W···O10.90 (3)1.85 (2)2.732 (4)164 (4)
O13—H8W···O14iv0.90 (3)1.95 (2)2.820 (5)163 (5)
O14—H9W···O7v0.90 (3)1.84 (3)2.740 (4)176 (4)
O14—H10W···O150.90 (3)1.97 (2)2.817 (4)157 (5)
O15—H11W···O30.90 (3)2.02 (2)2.922 (4)176 (3)
O15—H12W···O12vi0.90 (3)1.92 (2)2.787 (4)161 (4)
Symmetry codes: (i) x+1, y, z+2; (ii) x+1, y, z+1; (iii) x+1/2, y+1/2, z1/2; (iv) x+1/2, y1/2, z+3/2; (v) x1/2, y+1/2, z1/2; (vi) x1/2, y+1/2, z+1/2.

Experimental details

Crystal data
Chemical formula[Fe(C12H8N2)3](C7H4NO3S)2·C7H5NO3S·6H2O
Mr1252.08
Crystal system, space groupMonoclinic, P21/n
Temperature (K)120
a, b, c (Å)16.113 (4), 19.079 (5), 17.227 (4)
β (°) 92.873 (5)
V3)5289 (2)
Z4
Radiation typeMo Kα
µ (mm1)0.49
Crystal size (mm)0.48 × 0.19 × 0.10
Data collection
DiffractometerBruker SMART-CCD
diffractometer
Absorption correctionIntegration
(SHELXTL-NT; Bruker, 1998)
Tmin, Tmax0.830, 0.954
No. of measured, independent and
observed [I > 2σ(I)] reflections
47439, 14753, 7374
Rint0.115
(sin θ/λ)max1)0.713
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.056, 0.145, 0.99
No. of reflections14753
No. of parameters812
No. of restraints18
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.52, 0.70

Computer programs: SMART-NT (Bruker, 1998), SMART-NT, SAINT-NT (Bruker, 1998), SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), SHELXTL-NT (Bruker, 1998).

Selected geometric parameters (Å, º) top
Fe1—N11.965 (3)Fe1—N41.973 (3)
Fe1—N21.963 (3)Fe1—N51.963 (3)
Fe1—N31.974 (3)Fe1—N61.957 (3)
N1—Fe1—N282.55 (11)N2—Fe1—N693.44 (11)
N1—Fe1—N391.50 (11)N3—Fe1—N482.77 (11)
N1—Fe1—N494.89 (11)N3—Fe1—N593.00 (11)
N1—Fe1—N5173.96 (11)N3—Fe1—N6173.03 (11)
N1—Fe1—N693.15 (11)N4—Fe1—N589.67 (10)
N2—Fe1—N392.31 (11)N4—Fe1—N691.66 (11)
N2—Fe1—N4174.42 (11)N5—Fe1—N682.75 (11)
N2—Fe1—N593.23 (11)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N8—H8N···O110.92 (5)1.70 (5)2.614 (4)174 (4)
O10—H1W···O40.89 (4)2.19 (2)2.989 (4)148 (4)
O10—H2W···O13i0.90 (3)1.87 (3)2.756 (4)171 (5)
O11—H3W···O100.90 (3)1.87 (4)2.740 (4)161 (5)
O11—H4W···O70.90 (3)1.85 (3)2.741 (3)174 (4)
O12—H5W···N7ii0.90 (3)2.70 (2)3.547 (5)157 (5)
O12—H6W···O9iii0.90 (3)2.13 (4)2.917 (4)146 (5)
O13—H7W···O10.90 (3)1.85 (2)2.732 (4)164 (4)
O13—H8W···O14iv0.90 (3)1.95 (2)2.820 (5)163 (5)
O14—H9W···O7v0.90 (3)1.84 (3)2.740 (4)176 (4)
O14—H10W···O150.90 (3)1.97 (2)2.817 (4)157 (5)
O15—H11W···O30.90 (3)2.02 (2)2.922 (4)176 (3)
O15—H12W···O12vi0.90 (3)1.92 (2)2.787 (4)161 (4)
Symmetry codes: (i) x+1, y, z+2; (ii) x+1, y, z+1; (iii) x+1/2, y+1/2, z1/2; (iv) x+1/2, y1/2, z+3/2; (v) x1/2, y+1/2, z1/2; (vi) x1/2, y+1/2, z+1/2.
 

Subscribe to Acta Crystallographica Section C: Structural Chemistry

The full text of this article is available to subscribers to the journal.

If you have already registered and are using a computer listed in your registration details, please email support@iucr.org for assistance.

Buy online

You may purchase this article in PDF and/or HTML formats. For purchasers in the European Community who do not have a VAT number, VAT will be added at the local rate. Payments to the IUCr are handled by WorldPay, who will accept payment by credit card in several currencies. To purchase the article, please complete the form below (fields marked * are required), and then click on `Continue'.
E-mail address* 
Repeat e-mail address* 
(for error checking) 

Format*   PDF (US $40)
   HTML (US $40)
   PDF+HTML (US $50)
In order for VAT to be shown for your country javascript needs to be enabled.

VAT number 
(non-UK EC countries only) 
Country* 
 

Terms and conditions of use
Contact us

Follow Acta Cryst. C
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds