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Acta Cryst. (2008). E64, m240-m241    [ doi:10.1107/S1600536807066895 ]

Diacetonitriletetrakis{[mu]2-3-anilinocarbonyl-1-[(5-chloro-2-oxidophenyl)diazenyl]-2-naphtholato}tetraaquadiiron(III)disodium(I) dihydrate

S. Yohei, U. Kazuya and J. Mizuguchi

Abstract top

The title compound, [Fe2Na2(C23H14ClN3O3)4(C2H3N)2(H2O)4]·2H2O, is a hydrated Fe-azo complex dimer that is used as a charge-control agent in electrophotography. The molecule is a centrosymmetric dimer with two octahedral FeIII units linked by two bridging five-coordinate NaI cations. Each FeIII atom is chelated by the N and two O atoms from two 3-anilinocarbonyl-1-[(5-chloro-2-oxidophenyl)diazenyl]-2-naphtholate ligands. The Na+ cation is coordinated by a carbonyl O atom from the two ligands of each octahedral FeIII unit, two water molecules and the N atom of an acetonitrile molecule. Two solvent water molecules complete the structure. In the crystal structure, the dimeric molecules are bridged by a pair of discrete intermolecular O-H...O hydrogen bonds, one of which involves a sodium-bound water molecule and a hydrate water, and the other a 5-chlorophenolate O atom and a water molecule to form an extended chain along b.

Comment top

The title compound, I, is a hydrated Fe-azo complex dimer that is used as a charge-control agent (CCA) of the negative type in electrophotography (Tanaka, 1995). The purpose of the investigation has been set out in our previous paper (Mizuguchi, Sato, Uta & Sato, 2007). We have previously reported the structure of a methanol-solvated Fe-azo complex with an ammonium cation (Mizuguchi et al., 2007a) and its acetone solvate (Mizuguchi, Uta & Sato, 2007). together with the structure of an acetone-solvated Fe-azo complex with a sodium cation, in place of the ammonium (Mizuguchi et al., 2007b). In this molecule, the sodium cation is found to bridge three different Fe-azo complexes through the Na—O bonds between the sodium cation and the carbonyl O atoms of the Fe-azo complex. The present paper reports a related hydrated Fe-azo complex dimer bridged by two sodium cations.

Fig. 1 shows the asymmetric unit of the complex with the complete centrosymmetric dimer molecule shown in Fig. 2. The dimer comprises two octahedral FeIII units linked by two bridging five-coordinate NaI cations. Each FeIII atom is chelated by the N and two O atoms from two 3-anilinocarbonyl-1-[(5-chloro-2-oxidophenyl)diazenyl]-2-naphtholate ligands with the naphtholate and chloro-2-oxidophenyl O atoms mutually cis. In each octahedral FeIII unit, there are two intramolecular N3—H3N···O1 and N6—H6N···O3 hydrogen bonds that effect the conformation of the molecule (Table 2). The five-coordinate Na cation binds to N7 of the acetonitrile molecule, the O7 and O8 atoms of the two coordinated water molecules, and to the O6 and O5i carbonyl O atoms from of each octahedral FeIII unit [symmetry code (i): 1 - x, -y, 1 - z]). There are also two hydrated water molecules O9 and O9ii [symmetry code (ii): x, y - 1,z].

In the crystal structure the dimeric molecules are bridged by a pair of discrete intermolecular O—H···O hydrogen bonds as shown in Fig. 3. One of these involves a sodium bound water molecule and a hydrate water, and the other a 5-chlorphenolate O atom and a hydrate water to form an extended chain along b. The atoms involved are: O8—(H)···O9 and O9—(H)···O4ii [symmetry code: (ii) x, -1 + y, z] with the H atoms in parenthesis not located. The H atoms on the O7, O8 and O9 atoms of the water molecules could not be found in difference density maps. However the bond distances O8—O9, 2.730 (7) and O9—O4ii, 2.710 (6) Å [symmetry code: (ii) x, -1 + y, z] strongly suggest the presence of classical hydrogen bonds.

Related literature top

For general background to charge-control agents, see: Tanaka (1995) and for the preparation of the title compound, see: Yasumatsu et al. (2006). For related structures, see: Mizuguchi, Sato, Uta & Sato (2007); Mizuguchi et al. (2007a,b); Mizuguchi, Uta & Sato (2007).

Experimental top

Compound I was prepared according to the previously reported method (Yasumatsu et al., 2006). Single crystals of (I) were recrystallized from an acetonitrile solution as blocks over a 48 h period.

Refinement top

All H atoms were placed in geometrically idealized positions and constrained to ride on their parent atoms, with C—H = 0.93 except for C—H in methyl groups (0.96) and N—H = 0.86 A, and Uiso (H) = 1.2 Ueq (parent atom). Six H atoms on the three water molecules (O7, O8 and O9) were not located in difference electron density maps.

R-merge for the reflection data was 12.5%. This indicates poor crystal quality resulting in a rather high value of the R factor.

Computing details top

Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO (Rigaku, 1998); data reduction: CrystalStructure (Rigaku/MSC, 2006); program(s) used to solve structure: SIR2004 (Burla et al., 2005); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996); software used to prepare material for publication: CrystalStructure (Rigaku/MSC, 2006).

Figures top
[Figure 1] Fig. 1. A view of the molecular structure of (I), showing 30% displacement ellipsoids.
[Figure 2] Fig. 2. The centrosymmetric complex dimer. The two Fe-azo complexes are bridged by Na1 and Na1i cations through Na1—O5i and Na1—O6, and Na1i—O5 and Na1i—O6i bonds, respectively [symmetry code(i): 1 - x, -y, 1 - z].
[Figure 3] Fig. 3. shows two distinct intermolecular O···O interactions, dashed lines, that link two azo-Fe complex dimers: O8···O9 and O9···O4ii Hydrogen atoms on O8 and O9 could not be located in difference electron density maps [symmetry codes (i): -x + 1, -y, -z + 1 and (ii): x, -1 + y, z].
Diacetonitriletetrakis{µ2-3-anilinocarbonyl-1-[(5-chloro-2- oxidophenyl)diazenyl]-2-naphtholato}tetraaquadiiron(III)disodium(I) dihydrate top
Crystal data top
[Fe2Na2(C23H14ClN3O3)4(C2H3N)2(H2O)4]·2H2OZ = 1
Mr = 2011.21F(000) = 1022.0
Triclinic, P1Dx = 1.481 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71075 Å
a = 11.4416 (5) ÅCell parameters from 18467 reflections
b = 14.1161 (7) Åθ = 3.0–25.3°
c = 15.0105 (7) ŵ = 0.53 mm−1
α = 72.396 (1)°T = 93 K
β = 76.2850 (9)°Block, black
γ = 83.015 (1)°0.30 × 0.09 × 0.05 mm
V = 2241.67 (18) Å3
Data collection top
Rigaku R-AXIS RAPID
diffractometer		4163 reflections with I > 2σ(I)
Detector resolution: 10.00 pixels mm-1Rint = 0.125
ω scansθmax = 25.4°
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)		h = −13→13
Tmin = 0.793, Tmax = 0.976k = −16→16
40907 measured reflectionsl = −18→18
8133 independent reflections
Refinement top
Refinement on F20 restraints
R[F2 > 2σ(F2)] = 0.086H-atom parameters constrained
wR(F2) = 0.264 w = 1/[σ2(Fo2) + (0.1531P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.97(Δ/σ)max < 0.001
8133 reflectionsΔρmax = 1.17 e Å−3
607 parametersΔρmin = −1.00 e Å−3
Crystal data top
[Fe2Na2(C23H14ClN3O3)4(C2H3N)2(H2O)4]·2H2Oγ = 83.015 (1)°
Mr = 2011.21V = 2241.67 (18) Å3
Triclinic, P1Z = 1
a = 11.4416 (5) ÅMo Kα radiation
b = 14.1161 (7) ŵ = 0.53 mm−1
c = 15.0105 (7) ÅT = 93 K
α = 72.396 (1)°0.30 × 0.09 × 0.05 mm
β = 76.2850 (9)°
Data collection top
Rigaku R-AXIS RAPID
diffractometer		8133 independent reflections
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)		4163 reflections with I > 2σ(I)
Tmin = 0.793, Tmax = 0.976Rint = 0.125
40907 measured reflectionsθmax = 25.4°
Refinement top
R[F2 > 2σ(F2)] = 0.086H-atom parameters constrained
wR(F2) = 0.264Δρmax = 1.17 e Å−3
S = 0.97Δρmin = −1.00 e Å−3
8133 reflectionsAbsolute structure: ?
607 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
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
xyzUiso*/Ueq
Fe10.35889 (7)0.15898 (6)0.81868 (6)0.0419 (3)
Cl10.89755 (14)0.08974 (12)0.97345 (11)0.0493 (4)
Cl2−0.13236 (15)0.46998 (12)0.94460 (12)0.0570 (4)
Na10.1669 (2)−0.2788 (2)0.66698 (19)0.0631 (7)
O10.3035 (3)0.0314 (2)0.8208 (2)0.0431 (9)
O20.2505 (3)0.1532 (2)0.9412 (2)0.0455 (10)
O30.4037 (3)0.1844 (2)0.6776 (2)0.0441 (10)
O40.4653 (3)0.2573 (2)0.8224 (2)0.0435 (10)
O50.6633 (4)0.2145 (3)0.4266 (3)0.0565 (11)
O60.1263 (3)−0.1752 (3)0.7588 (2)0.0506 (11)
O70.0555 (5)−0.1671 (4)0.5459 (4)0.1103 (15)
O80.2170 (5)−0.4270 (4)0.7749 (4)0.1103 (15)
O90.3764 (4)−0.5671 (3)0.8564 (3)0.0660 (13)
N10.5057 (4)0.0648 (3)0.8650 (3)0.0397 (11)
N20.5346 (4)−0.0289 (3)0.8773 (3)0.0398 (11)
N30.1124 (4)−0.0205 (3)0.7800 (3)0.0454 (12)
N40.2318 (4)0.2816 (3)0.7769 (3)0.0413 (11)
N50.2329 (4)0.3526 (3)0.6989 (3)0.0430 (12)
N60.5554 (4)0.1015 (3)0.5544 (3)0.0449 (12)
N7−0.0136 (6)−0.3582 (5)0.6870 (6)0.101 (2)
C10.5628 (5)0.2210 (4)0.8598 (4)0.0422 (14)
C20.6393 (5)0.2825 (4)0.8750 (4)0.0448 (15)
C30.7400 (5)0.2409 (4)0.9114 (4)0.0473 (15)
C40.7679 (5)0.1382 (4)0.9319 (4)0.0451 (14)
C50.6932 (5)0.0759 (4)0.9196 (4)0.0428 (14)
C60.5913 (5)0.1184 (4)0.8821 (4)0.0436 (14)
C70.3479 (5)−0.0602 (4)0.8343 (4)0.0392 (13)
C80.4605 (5)−0.0899 (4)0.8615 (4)0.0386 (13)
C90.5082 (5)−0.1914 (4)0.8752 (4)0.0402 (14)
C100.6220 (5)−0.2231 (4)0.8991 (4)0.0486 (15)
C110.6632 (6)−0.3209 (4)0.9089 (5)0.0593 (18)
C120.5984 (6)−0.3902 (4)0.8959 (5)0.0592 (18)
C130.4881 (6)−0.3611 (4)0.8720 (5)0.0544 (17)
C140.4414 (5)−0.2609 (4)0.8604 (4)0.0454 (15)
C150.3295 (5)−0.2294 (4)0.8330 (4)0.0450 (14)
C160.2828 (5)−0.1335 (4)0.8186 (4)0.0398 (13)
C170.1688 (5)−0.1119 (4)0.7845 (4)0.0424 (14)
C180.0062 (5)0.0210 (4)0.7457 (4)0.0452 (15)
C19−0.0736 (6)−0.0332 (5)0.7267 (4)0.0573 (17)
C20−0.1751 (6)0.0128 (5)0.6939 (4)0.0605 (18)
C21−0.1973 (6)0.1163 (5)0.6778 (4)0.0573 (18)
C22−0.1186 (5)0.1703 (5)0.6963 (4)0.0530 (17)
C23−0.0168 (5)0.1234 (5)0.7317 (4)0.0502 (16)
C240.1631 (5)0.2232 (4)0.9440 (4)0.0415 (14)
C250.0855 (5)0.2317 (4)1.0296 (4)0.0434 (14)
C26−0.0026 (5)0.3072 (4)1.0291 (4)0.0471 (15)
C27−0.0182 (5)0.3765 (4)0.9418 (4)0.0444 (14)
C280.0548 (5)0.3704 (4)0.8564 (4)0.0468 (15)
C290.1455 (5)0.2944 (4)0.8573 (4)0.0421 (14)
C300.4013 (5)0.2678 (4)0.6089 (4)0.0452 (15)
C310.3192 (5)0.3486 (4)0.6182 (4)0.0456 (15)
C320.3197 (5)0.4395 (4)0.5399 (4)0.0437 (14)
C330.2371 (5)0.5215 (4)0.5450 (4)0.0484 (15)
C340.2456 (6)0.6069 (4)0.4700 (4)0.0541 (17)
C350.3359 (6)0.6164 (4)0.3864 (4)0.0548 (17)
C360.4139 (6)0.5365 (4)0.3802 (4)0.0510 (16)
C370.4090 (5)0.4471 (4)0.4548 (4)0.0442 (14)
C380.4904 (5)0.3653 (4)0.4471 (4)0.0476 (15)
C390.4874 (5)0.2775 (4)0.5180 (4)0.0452 (15)
C400.5767 (6)0.1949 (5)0.4971 (4)0.0505 (16)
C410.6173 (5)0.0108 (4)0.5470 (4)0.0435 (14)
C420.7141 (5)0.0022 (5)0.4734 (4)0.0564 (17)
C430.7690 (6)−0.0910 (5)0.4735 (5)0.068 (2)
C440.7300 (6)−0.1763 (5)0.5459 (4)0.0577 (17)
C450.6337 (5)−0.1664 (5)0.6187 (4)0.0523 (16)
C460.5787 (5)−0.0738 (4)0.6184 (4)0.0462 (15)
C47−0.0920 (8)−0.4004 (6)0.6882 (6)0.081 (2)
C48−0.1940 (8)−0.4558 (7)0.6902 (6)0.103 (3)
H20.62240.35090.86050.054*
H30.78990.28160.92240.057*
H3N0.14560.01760.80080.054*
H50.70970.00740.93560.051*
H6N0.49580.09700.60240.054*
H100.6683−0.17840.90820.058*
H110.7379−0.34100.92480.071*
H120.6288−0.45570.90330.071*
H130.4439−0.40720.86340.066*
H150.2858−0.27580.82420.053*
H19−0.0590−0.10180.73630.068*
H20−0.2287−0.02450.68250.073*
H21−0.26490.14780.65480.069*
H22−0.13290.23880.68520.064*
H230.03500.16020.74570.060*
H250.09400.18571.08720.052*
H26−0.05210.31281.08630.057*
H280.04410.41590.79910.056*
H330.17650.51770.59950.058*
H340.19010.66000.47470.065*
H350.34210.67540.33690.066*
H360.47260.54120.32460.061*
H380.54890.37130.39110.057*
H420.74180.05830.42460.068*
H430.8335−0.09670.42390.082*
H440.7678−0.23840.54530.069*
H450.6060−0.22220.66790.063*
H460.5138−0.06840.66770.055*
H48A−0.1883−0.46350.62790.123*
H48B−0.2682−0.41980.70810.123*
H48C−0.1919−0.52020.73580.123*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Fe10.0437 (5)0.0388 (5)0.0420 (5)0.0055 (3)−0.0130 (4)−0.0097 (3)
Cl10.0459 (8)0.0517 (9)0.0505 (9)0.0036 (7)−0.0165 (7)−0.0122 (7)
Cl20.0557 (10)0.0513 (10)0.0614 (11)0.0143 (7)−0.0124 (8)−0.0188 (8)
Na10.0676 (17)0.0632 (18)0.0588 (17)−0.0126 (14)0.0001 (13)−0.0248 (13)
O10.044 (2)0.040 (2)0.046 (2)0.0014 (18)−0.0145 (19)−0.0111 (18)
O20.049 (2)0.041 (2)0.047 (2)0.0134 (19)−0.0170 (19)−0.0129 (19)
O30.049 (2)0.040 (2)0.041 (2)0.0019 (18)−0.0088 (19)−0.0106 (18)
O40.044 (2)0.040 (2)0.049 (2)0.0070 (18)−0.0202 (19)−0.0115 (18)
O50.057 (2)0.054 (2)0.052 (2)0.006 (2)−0.002 (2)−0.016 (2)
O60.049 (2)0.053 (2)0.051 (2)−0.001 (2)−0.013 (2)−0.014 (2)
O70.114 (3)0.112 (3)0.107 (3)−0.011 (2)−0.047 (3)−0.014 (2)
O80.114 (3)0.112 (3)0.107 (3)−0.011 (2)−0.047 (3)−0.014 (2)
O90.067 (3)0.050 (2)0.084 (3)−0.001 (2)−0.019 (2)−0.022 (2)
N10.038 (2)0.040 (2)0.039 (2)0.001 (2)−0.007 (2)−0.011 (2)
N20.050 (3)0.033 (2)0.034 (2)0.005 (2)−0.011 (2)−0.009 (2)
N30.046 (2)0.046 (3)0.047 (3)0.003 (2)−0.015 (2)−0.016 (2)
N40.042 (2)0.040 (2)0.041 (2)0.001 (2)−0.009 (2)−0.012 (2)
N50.049 (3)0.040 (2)0.033 (2)0.003 (2)−0.010 (2)−0.002 (2)
N60.050 (3)0.039 (3)0.041 (2)0.003 (2)−0.008 (2)−0.009 (2)
N70.073 (4)0.088 (5)0.164 (8)0.003 (4)−0.057 (5)−0.047 (5)
C10.042 (3)0.047 (3)0.037 (3)0.003 (2)−0.010 (2)−0.012 (2)
C20.048 (3)0.037 (3)0.051 (3)0.010 (2)−0.022 (3)−0.010 (2)
C30.046 (3)0.044 (3)0.052 (4)−0.002 (2)−0.005 (3)−0.017 (2)
C40.045 (3)0.046 (3)0.047 (3)−0.001 (2)−0.014 (2)−0.014 (2)
C50.048 (3)0.041 (3)0.042 (3)0.007 (2)−0.018 (2)−0.013 (2)
C60.050 (3)0.038 (3)0.042 (3)0.001 (2)−0.016 (2)−0.008 (2)
C70.046 (3)0.034 (3)0.041 (3)0.005 (2)−0.011 (2)−0.018 (2)
C80.038 (3)0.038 (3)0.039 (3)0.010 (2)−0.016 (2)−0.009 (2)
C90.044 (3)0.038 (3)0.039 (3)0.007 (2)−0.010 (2)−0.013 (2)
C100.057 (3)0.040 (3)0.052 (3)0.003 (3)−0.020 (3)−0.012 (2)
C110.052 (4)0.050 (4)0.080 (5)0.016 (3)−0.029 (3)−0.021 (3)
C120.060 (4)0.038 (3)0.089 (5)0.017 (3)−0.034 (3)−0.024 (3)
C130.059 (4)0.039 (3)0.072 (4)−0.001 (3)−0.019 (3)−0.022 (3)
C140.050 (3)0.038 (3)0.048 (3)0.003 (2)−0.010 (2)−0.015 (2)
C150.043 (3)0.044 (3)0.049 (3)−0.001 (2)−0.010 (2)−0.015 (2)
C160.040 (3)0.043 (3)0.039 (3)0.003 (2)−0.017 (2)−0.010 (2)
C170.047 (3)0.037 (3)0.041 (3)0.005 (2)−0.011 (2)−0.010 (2)
C180.042 (3)0.054 (4)0.040 (3)0.005 (3)−0.013 (2)−0.014 (2)
C190.055 (4)0.060 (4)0.059 (4)0.014 (3)−0.024 (3)−0.018 (3)
C200.058 (4)0.070 (5)0.055 (4)0.003 (3)−0.019 (3)−0.017 (3)
C210.055 (4)0.061 (4)0.060 (4)0.015 (3)−0.026 (3)−0.019 (3)
C220.049 (3)0.059 (4)0.048 (4)0.019 (3)−0.019 (3)−0.013 (3)
C230.049 (3)0.057 (4)0.043 (3)0.005 (3)−0.007 (2)−0.016 (3)
C240.047 (3)0.037 (3)0.040 (3)−0.001 (2)−0.011 (2)−0.009 (2)
C250.048 (3)0.039 (3)0.042 (3)0.002 (2)−0.015 (2)−0.006 (2)
C260.046 (3)0.049 (3)0.048 (3)0.003 (3)−0.012 (2)−0.017 (3)
C270.046 (3)0.038 (3)0.051 (3)0.015 (2)−0.016 (2)−0.016 (2)
C280.053 (3)0.039 (3)0.047 (3)0.005 (2)−0.013 (3)−0.012 (2)
C290.037 (3)0.041 (3)0.048 (3)0.004 (2)−0.014 (2)−0.011 (2)
C300.053 (3)0.041 (3)0.037 (3)−0.003 (2)−0.012 (2)−0.003 (2)
C310.058 (4)0.034 (3)0.046 (3)0.008 (2)−0.018 (3)−0.013 (2)
C320.050 (3)0.042 (3)0.037 (3)0.002 (2)−0.012 (2)−0.007 (2)
C330.055 (3)0.045 (3)0.046 (3)0.006 (3)−0.013 (3)−0.014 (2)
C340.061 (4)0.040 (3)0.058 (4)0.011 (3)−0.019 (3)−0.009 (3)
C350.073 (4)0.045 (4)0.041 (3)−0.003 (3)−0.009 (3)−0.006 (2)
C360.062 (4)0.047 (4)0.043 (3)−0.003 (3)−0.011 (3)−0.011 (2)
C370.051 (3)0.043 (3)0.037 (3)0.006 (2)−0.013 (2)−0.010 (2)
C380.057 (4)0.045 (3)0.039 (3)−0.004 (3)−0.008 (3)−0.010 (2)
C390.043 (3)0.047 (3)0.047 (3)0.006 (2)−0.014 (2)−0.015 (2)
C400.056 (4)0.054 (4)0.044 (3)0.004 (3)−0.015 (3)−0.015 (3)
C410.050 (3)0.041 (3)0.043 (3)0.002 (2)−0.015 (2)−0.014 (2)
C420.060 (4)0.046 (4)0.051 (4)0.000 (3)0.000 (3)−0.006 (3)
C430.070 (4)0.052 (4)0.064 (4)−0.001 (3)0.010 (3)−0.008 (3)
C440.064 (4)0.050 (4)0.052 (4)0.013 (3)−0.006 (3)−0.015 (3)
C450.054 (4)0.048 (4)0.051 (4)−0.004 (3)−0.011 (3)−0.010 (3)
C460.047 (3)0.047 (3)0.041 (3)0.003 (2)−0.010 (2)−0.009 (2)
C470.069 (5)0.086 (6)0.089 (6)0.012 (4)−0.027 (4)−0.024 (4)
C480.097 (7)0.106 (7)0.105 (7)−0.010 (5)−0.039 (6)−0.015 (5)
Geometric parameters (Å, º) top
Fe1—O11.970 (4)C15—C161.366 (8)
Fe1—O21.944 (3)C15—H150.930
Fe1—O31.986 (3)C16—C171.477 (8)
Fe1—O41.976 (4)C18—C191.387 (11)
Fe1—N12.127 (4)C18—C231.397 (9)
Fe1—N42.161 (4)C19—C201.381 (10)
Cl1—C41.729 (6)C19—H190.930
Cl2—C271.743 (6)C20—C211.408 (10)
Na1—O5i2.222 (4)C20—H200.930
Na1—O62.238 (5)C21—C221.373 (11)
Na1—O72.508 (7)C21—H210.930
Na1—O82.329 (6)C22—C231.404 (9)
Na1—N72.381 (9)C22—H220.930
O1—C71.304 (6)C23—H230.930
O2—C241.320 (6)C24—C251.407 (8)
O3—C301.312 (6)C24—C291.424 (7)
O4—C11.344 (7)C25—C261.375 (8)
O5—C401.253 (7)C25—H250.930
O6—C171.258 (8)C26—C271.413 (8)
N1—N21.290 (6)C26—H260.930
N1—C61.420 (9)C27—C281.375 (8)
N2—C81.384 (8)C28—C291.398 (8)
N3—C171.361 (7)C28—H280.930
N3—C181.424 (8)C30—C311.406 (8)
N3—H3N0.860C30—C391.460 (8)
N4—N51.289 (5)C31—C321.455 (7)
N4—C291.409 (7)C32—C331.412 (8)
N5—C311.380 (7)C32—C371.418 (7)
N6—C401.353 (7)C33—C341.373 (7)
N6—C411.407 (7)C33—H330.930
N6—H6N0.860C34—C351.406 (8)
N7—C471.130 (13)C34—H340.930
C1—C21.404 (10)C35—C361.363 (9)
C1—C61.400 (8)C35—H350.930
C2—C31.382 (8)C36—C371.408 (7)
C2—H20.930C36—H360.930
C3—C41.401 (8)C37—C381.408 (8)
C3—H30.930C38—C391.366 (7)
C4—C51.376 (10)C38—H380.930
C5—C61.404 (8)C39—C401.511 (9)
C5—H50.930C41—C421.390 (8)
C7—C81.420 (8)C41—C461.379 (7)
C7—C161.449 (9)C42—C431.387 (9)
C8—C91.441 (7)C42—H420.930
C9—C101.417 (8)C43—C441.393 (8)
C9—C141.410 (10)C43—H430.930
C10—C111.379 (9)C44—C451.382 (8)
C10—H100.930C44—H440.930
C11—C121.380 (11)C45—C461.379 (9)
C11—H110.930C45—H450.930
C12—C131.374 (10)C46—H460.930
C12—H120.930C47—C481.472 (14)
C13—C141.424 (8)C48—H48A0.960
C13—H130.930C48—H48B0.960
C14—C151.417 (9)C48—H48C0.960
O4···O9ii2.710 (6)O9···O4iii2.710 (6)
O8···O92.730 (7)O9···O82.730 (7)
O1—Fe1—O290.26 (17)N3—C17—C16117.7 (6)
O1—Fe1—O385.60 (17)N3—C18—C19124.4 (5)
O1—Fe1—O4160.14 (15)N3—C18—C23116.0 (6)
O1—Fe1—N181.72 (18)C19—C18—C23119.5 (5)
O1—Fe1—N4111.90 (19)C18—C19—C20120.8 (6)
O2—Fe1—O3155.71 (17)C18—C19—H19119.9
O2—Fe1—O496.86 (18)C20—C19—H19119.3
O2—Fe1—N1100.35 (16)C19—C20—C21119.9 (7)
O2—Fe1—N479.14 (16)C19—C20—H20120.1
O3—Fe1—O495.02 (17)C21—C20—H20120.1
O3—Fe1—N1102.70 (16)C20—C21—C22119.5 (6)
O3—Fe1—N480.26 (17)C20—C21—H21120.2
O4—Fe1—N178.78 (18)C22—C21—H21120.2
O4—Fe1—N487.69 (18)C21—C22—C23120.7 (6)
N1—Fe1—N4166.3 (2)C21—C22—H22119.6
O5i—Na1—O697.7 (2)C23—C22—H22119.6
O5i—Na1—O788.35 (19)C18—C23—C22119.5 (7)
O5i—Na1—O8108.0 (2)C18—C23—H23120.3
O5i—Na1—N7149.5 (3)C22—C23—H23120.3
O6—Na1—O792.9 (2)O2—C24—C25123.0 (4)
O6—Na1—O8101.3 (2)O2—C24—C29119.4 (4)
O6—Na1—N7107.6 (2)C25—C24—C29117.6 (5)
O7—Na1—O8156.4 (2)C24—C25—C26120.8 (5)
O7—Na1—N773.9 (2)C24—C25—H25119.6
O8—Na1—N783.8 (2)C26—C25—H25119.6
Fe1—O1—C7136.1 (4)C25—C26—C27120.2 (5)
Fe1—O2—C24117.8 (3)C25—C26—H26119.9
Fe1—O3—C30130.3 (4)C27—C26—H26119.9
Fe1—O4—C1116.7 (3)Cl2—C27—C26118.6 (4)
Na1i—O5—C40159.8 (5)Cl2—C27—C28120.6 (4)
Na1—O6—C17145.0 (3)C26—C27—C28120.8 (5)
Fe1—N1—N2133.6 (4)C27—C28—C29118.8 (5)
Fe1—N1—C6112.0 (3)C27—C28—H28120.6
N2—N1—C6114.3 (4)C29—C28—H28120.6
N1—N2—C8120.5 (4)N4—C29—C24112.6 (4)
C17—N3—C18129.2 (6)N4—C29—C28125.6 (5)
C17—N3—H3N115.4C24—C29—C28121.7 (5)
C18—N3—H3N115.4O3—C30—C31123.1 (5)
Fe1—N4—N5132.3 (3)O3—C30—C39118.8 (5)
Fe1—N4—C29110.8 (3)C31—C30—C39118.1 (4)
N5—N4—C29115.6 (4)N5—C31—C30125.8 (4)
N4—N5—C31119.2 (4)N5—C31—C32113.0 (5)
C40—N6—C41129.3 (4)C30—C31—C32121.1 (5)
C40—N6—H6N115.3C31—C32—C33123.2 (5)
C41—N6—H6N115.4C31—C32—C37118.6 (5)
Na1—N7—C47171.9 (8)C33—C32—C37118.2 (4)
O4—C1—C2122.4 (5)C32—C33—C34120.4 (5)
O4—C1—C6119.0 (6)C32—C33—H33119.8
C2—C1—C6118.5 (5)C34—C33—H33119.8
C1—C2—C3119.7 (5)C33—C34—C35121.9 (5)
C1—C2—H2120.1C33—C34—H34119.0
C3—C2—H2120.1C35—C34—H34119.0
C2—C3—C4120.8 (6)C34—C35—C36117.9 (5)
C2—C3—H3119.6C34—C35—H35121.1
C4—C3—H3119.6C36—C35—H35121.1
Cl1—C4—C3119.3 (5)C35—C36—C37122.6 (5)
Cl1—C4—C5120.0 (4)C35—C36—H36118.7
C3—C4—C5120.7 (5)C37—C36—H36118.7
C4—C5—C6118.3 (5)C32—C37—C36119.0 (5)
C4—C5—H5120.8C32—C37—C38119.2 (4)
C6—C5—H5120.8C36—C37—C38121.8 (5)
N1—C6—C1112.8 (5)C37—C38—C39123.0 (5)
N1—C6—C5125.3 (5)C37—C38—H38118.5
C1—C6—C5121.9 (6)C39—C38—H38118.5
O1—C7—C8121.8 (6)C30—C39—C38119.8 (5)
O1—C7—C16119.5 (5)C30—C39—C40123.5 (4)
C8—C7—C16118.7 (5)C38—C39—C40116.7 (5)
N2—C8—C7125.9 (5)O5—C40—N6123.1 (5)
N2—C8—C9113.4 (5)O5—C40—C39119.5 (5)
C7—C8—C9120.8 (6)N6—C40—C39117.3 (4)
C8—C9—C10122.4 (6)N6—C41—C42124.1 (4)
C8—C9—C14118.9 (5)N6—C41—C46117.0 (4)
C10—C9—C14118.7 (5)C42—C41—C46118.9 (5)
C9—C10—C11119.3 (6)C41—C42—C43119.3 (5)
C9—C10—H10120.4C41—C42—H42120.3
C11—C10—H10120.4C43—C42—H42120.3
C10—C11—C12122.8 (6)C42—C43—C44121.6 (6)
C10—C11—H11118.6C42—C43—H43119.2
C12—C11—H11118.6C44—C43—H43119.2
C11—C12—C13119.0 (6)C43—C44—C45118.3 (6)
C11—C12—H12120.5C43—C44—H44120.8
C13—C12—H12120.5C45—C44—H44120.8
C12—C13—C14120.7 (7)C44—C45—C46120.1 (5)
C12—C13—H13119.5C44—C45—H45119.9
C14—C13—H13119.8C46—C45—H45120.0
C9—C14—C13119.6 (5)C41—C46—C45121.8 (5)
C9—C14—C15119.3 (5)C41—C46—H46119.1
C13—C14—C15121.1 (6)C45—C46—H46119.1
C14—C15—C16123.0 (6)N7—C47—C48179.8 (9)
C14—C15—H15118.7C47—C48—H48A109.5
C16—C15—H15118.3C47—C48—H48B109.5
C7—C16—C15119.3 (5)C47—C48—H48C109.5
C7—C16—C17124.6 (5)H48A—C48—H48B109.5
C15—C16—C17116.1 (6)H48A—C48—H48C109.5
O6—C17—N3121.1 (5)H48B—C48—H48C109.5
O6—C17—C16121.2 (5)
O1—Fe1—O2—C24−116.4 (4)C3—C4—C5—C62.7 (8)
O2—Fe1—O1—C7−107.1 (5)C4—C5—C6—N1179.9 (4)
O1—Fe1—O3—C30145.6 (5)C4—C5—C6—C1−1.8 (8)
O3—Fe1—O1—C796.8 (5)O1—C7—C8—N20.3 (6)
O1—Fe1—O4—C1−18.3 (7)O1—C7—C8—C9−179.5 (4)
O4—Fe1—O1—C74.2 (8)O1—C7—C16—C15−179.8 (3)
O1—Fe1—N1—N24.6 (4)O1—C7—C16—C172.3 (8)
O1—Fe1—N1—C6−178.2 (3)C8—C7—C16—C151.8 (7)
N1—Fe1—O1—C7−6.7 (5)C8—C7—C16—C17−176.1 (5)
O1—Fe1—N4—N5−105.7 (6)C16—C7—C8—N2178.7 (4)
O1—Fe1—N4—C2988.5 (4)C16—C7—C8—C9−1.2 (7)
N4—Fe1—O1—C7174.5 (4)N2—C8—C9—C10−2.1 (7)
O2—Fe1—O3—C3064.8 (7)N2—C8—C9—C14−179.5 (4)
O3—Fe1—O2—C24−36.6 (7)C7—C8—C9—C10177.8 (5)
O2—Fe1—O4—C191.9 (3)C7—C8—C9—C140.4 (6)
O4—Fe1—O2—C2482.2 (4)C8—C9—C10—C11−178.4 (5)
O2—Fe1—N1—N293.4 (4)C8—C9—C14—C13178.9 (5)
O2—Fe1—N1—C6−89.4 (3)C8—C9—C14—C15−0.2 (6)
N1—Fe1—O2—C24162.0 (4)C10—C9—C14—C131.4 (8)
O2—Fe1—N4—N5168.5 (6)C10—C9—C14—C15−177.7 (5)
O2—Fe1—N4—C292.6 (4)C14—C9—C10—C11−1.0 (8)
N4—Fe1—O2—C24−4.1 (4)C9—C10—C11—C120.2 (7)
O3—Fe1—O4—C1−109.3 (3)C10—C11—C12—C130.2 (7)
O4—Fe1—O3—C30−54.3 (5)C11—C12—C13—C140.2 (7)
O3—Fe1—N1—N2−78.9 (4)C12—C13—C14—C9−1.0 (9)
O3—Fe1—N1—C698.3 (3)C12—C13—C14—C15178.1 (6)
N1—Fe1—O3—C30−133.9 (5)C9—C14—C15—C160.9 (8)
O3—Fe1—N4—N5−24.5 (6)C13—C14—C15—C16−178.2 (5)
O3—Fe1—N4—C29169.7 (4)C14—C15—C16—C7−1.7 (8)
N4—Fe1—O3—C3032.5 (5)C14—C15—C16—C17176.4 (5)
O4—Fe1—N1—N2−171.6 (4)C7—C16—C17—O6169.3 (5)
O4—Fe1—N1—C65.6 (3)C7—C16—C17—N3−9.5 (7)
N1—Fe1—O4—C1−7.3 (3)C15—C16—C17—O6−8.7 (7)
O4—Fe1—N4—N571.0 (6)C15—C16—C17—N3172.5 (4)
O4—Fe1—N4—C29−94.8 (4)N3—C18—C19—C20179.7 (5)
N4—Fe1—O4—C1170.7 (3)N3—C18—C23—C22178.8 (5)
N1—Fe1—N4—N579.3 (10)C19—C18—C23—C22−1.7 (8)
N1—Fe1—N4—C29−86.5 (7)C23—C18—C19—C200.2 (7)
N4—Fe1—N1—N2179.9 (5)C18—C19—C20—C211.1 (9)
N4—Fe1—N1—C6−2.9 (9)C19—C20—C21—C22−1.0 (9)
O5i—Na1—O6—C17−15.9 (6)C20—C21—C22—C23−0.4 (8)
O6—Na1—O5i—C40i−161.4 (11)C21—C22—C23—C181.8 (8)
O7—Na1—O5i—C40i−68.7 (12)O2—C24—C25—C26178.6 (6)
O8—Na1—O5i—C40i94.0 (12)O2—C24—C29—N4−2.4 (9)
N7—Na1—O5i—C40i−15.1 (14)O2—C24—C29—C28−179.6 (6)
O7—Na1—O6—C17−104.7 (6)C25—C24—C29—N4177.1 (6)
O8—Na1—O6—C1794.3 (6)C25—C24—C29—C280.0 (9)
N7—Na1—O6—C17−178.7 (6)C29—C24—C25—C26−1.0 (10)
Fe1—O1—C7—C85.8 (8)C24—C25—C26—C271.3 (10)
Fe1—O1—C7—C16−172.5 (3)C25—C26—C27—Cl2179.2 (5)
Fe1—O2—C24—C25−174.4 (5)C25—C26—C27—C28−0.7 (10)
Fe1—O2—C24—C295.1 (8)Cl2—C27—C28—C29179.9 (4)
Fe1—O3—C30—C31−29.3 (10)C26—C27—C28—C29−0.3 (8)
Fe1—O3—C30—C39151.0 (5)C27—C28—C29—N4−176.1 (6)
Fe1—O4—C1—C2−173.9 (4)C27—C28—C29—C240.6 (10)
Fe1—O4—C1—C68.1 (6)O3—C30—C31—N50.9 (12)
Na1i—O5—C40—N6−117.5 (11)O3—C30—C31—C32−179.8 (6)
Na1i—O5—C40—C3965.3 (14)O3—C30—C39—C38−176.9 (6)
Na1—O6—C17—N3128.1 (5)O3—C30—C39—C402.4 (10)
Na1—O6—C17—C16−50.6 (8)C31—C30—C39—C383.4 (10)
Fe1—N1—N2—C8−1.7 (7)C31—C30—C39—C40−177.3 (7)
Fe1—N1—C6—C1−3.2 (5)C39—C30—C31—N5−179.4 (6)
Fe1—N1—C6—C5175.3 (4)C39—C30—C31—C320.0 (9)
N2—N1—C6—C1174.6 (4)N5—C31—C32—C33−2.4 (10)
N2—N1—C6—C5−7.0 (7)N5—C31—C32—C37176.3 (6)
C6—N1—N2—C8−178.9 (4)C30—C31—C32—C33178.2 (7)
N1—N2—C8—C7−2.0 (7)C30—C31—C32—C37−3.1 (10)
N1—N2—C8—C9177.9 (4)C31—C32—C33—C34177.1 (7)
C17—N3—C18—C1913.2 (8)C31—C32—C37—C36−177.0 (6)
C17—N3—C18—C23−167.3 (5)C31—C32—C37—C382.9 (10)
C18—N3—C17—O6−2.3 (8)C33—C32—C37—C361.7 (10)
C18—N3—C17—C16176.5 (4)C33—C32—C37—C38−178.3 (7)
Fe1—N4—N5—C3110.9 (9)C37—C32—C33—C34−1.6 (11)
Fe1—N4—C29—C24−0.9 (7)C32—C33—C34—C35−0.3 (9)
Fe1—N4—C29—C28176.0 (5)C33—C34—C35—C361.9 (12)
N5—N4—C29—C24−169.4 (5)C34—C35—C36—C37−1.7 (12)
N5—N4—C29—C287.6 (10)C35—C36—C37—C320.0 (10)
C29—N4—N5—C31176.2 (6)C35—C36—C37—C38180.0 (7)
N4—N5—C31—C307.2 (11)C32—C37—C38—C390.4 (11)
N4—N5—C31—C32−172.2 (6)C36—C37—C38—C39−179.6 (7)
C40—N6—C41—C42−2.0 (12)C37—C38—C39—C30−3.7 (11)
C40—N6—C41—C46177.4 (7)C37—C38—C39—C40177.0 (7)
C41—N6—C40—O5−2.7 (12)C30—C39—C40—O5−165.1 (7)
C41—N6—C40—C39174.5 (6)C30—C39—C40—N617.5 (11)
O4—C1—C2—C3−178.3 (5)C38—C39—C40—O514.1 (11)
O4—C1—C6—N1−2.8 (7)C38—C39—C40—N6−163.2 (7)
O4—C1—C6—C5178.7 (5)N6—C41—C42—C43179.6 (7)
C2—C1—C6—N1179.0 (4)N6—C41—C46—C45−179.3 (6)
C2—C1—C6—C50.5 (8)C42—C41—C46—C450.1 (8)
C6—C1—C2—C3−0.2 (6)C46—C41—C42—C430.2 (8)
C1—C2—C3—C41.1 (8)C41—C42—C43—C44−0.4 (10)
C2—C3—C4—Cl1177.8 (4)C42—C43—C44—C450.3 (9)
C2—C3—C4—C5−2.4 (8)C43—C44—C45—C460.1 (10)
Cl1—C4—C5—C6−177.5 (4)C44—C45—C46—C41−0.3 (9)
Symmetry codes: (i) −x+1, −y, −z+1; (ii) x, y+1, z; (iii) x, y−1, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H3N···O10.861.942.644 (7)138
N6—H6N···O30.861.972.664 (6)138
O8—H···O92.730 (7)
O9—H···O4iii2.710 (6)
Symmetry code: (iii) x, y−1, z.
Selected geometric parameters (Å, º) top
Fe1—O11.970 (4)Na1—O5i2.222 (4)
Fe1—O21.944 (3)Na1—O62.238 (5)
Fe1—O31.986 (3)Na1—O72.508 (7)
Fe1—O41.976 (4)Na1—O82.329 (6)
Fe1—N12.127 (4)Na1—N72.381 (9)
Fe1—N42.161 (4)
O4···O9ii2.710 (6)O9···O4iii2.710 (6)
O8···O92.730 (7)O9···O82.730 (7)
O1—Fe1—O290.26 (17)O4—Fe1—N487.69 (18)
O1—Fe1—O385.60 (17)N1—Fe1—N4166.3 (2)
O1—Fe1—O4160.14 (15)O5i—Na1—O697.7 (2)
O1—Fe1—N181.72 (18)O5i—Na1—O788.35 (19)
O1—Fe1—N4111.90 (19)O5i—Na1—O8108.0 (2)
O2—Fe1—O3155.71 (17)O5i—Na1—N7149.5 (3)
O2—Fe1—O496.86 (18)O6—Na1—O792.9 (2)
O2—Fe1—N1100.35 (16)O6—Na1—O8101.3 (2)
O2—Fe1—N479.14 (16)O6—Na1—N7107.6 (2)
O3—Fe1—O495.02 (17)O7—Na1—O8156.4 (2)
O3—Fe1—N1102.70 (16)O7—Na1—N773.9 (2)
O3—Fe1—N480.26 (17)O8—Na1—N783.8 (2)
O4—Fe1—N178.78 (18)
Symmetry codes: (i) −x+1, −y, −z+1; (ii) x, y+1, z; (iii) x, y−1, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H3N···O10.8601.9412.644 (7)138.0
N6—H6N···O30.8591.9672.664 (6)137.5
O8—H···O9..2.730 (7).
O9—H···O4iii..2.710 (6).
Symmetry code: (iii) x, y−1, z.
references
References top

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