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Acta Cryst. (2007). E63, m1377-m1378    [ doi:10.1107/S1600536807017369 ]

Poly[bis(acetone)bis[[mu]-4-[(5-chloro-2-oxidophenyl)diazenyl]-3-oxido-N-phenylnaphthalene-2-carboxamidato]sodium(I)ferrate(III)]

J. Mizuguchi, Y. Sato and K. Uta

Abstract top

The title compound, [FeNa(C23H14ClN3O3)2(C3H6O)2]n, has a skeleton of an azo-FeIII anion complex with a sodium cation, used widely as a charge-control agent (CCA) of the negative type in electrophotography. In the FeIII anion-complex, the FeIII atom is coordinated by four carbonyl O atoms and two N atoms of the diazo groups from two azo ligands lying cis to each other. There are two N-H...O intramolecular hydrogen bonds between the NH group and the carbonyl O atom. In the crystal structure, there exists a sodium-cation dimer bridged by the carbonyl O atoms at the periphery of the anion complex. An interesting aspect of this structure is that each sodium cation unites three different Fe-anion complexes through the carbonyl O atom, generating a quasi-two-dimensional network parallel to the (001) plane. At the same time, the sodium cation accommodates two acetone molecules, linked through the carbonyl O atom.

Comment top

Charge-control agents play an important role in the electrophotographic process and are usually added to toners to create a desired charge level and polarity. The purpose of the present investigation has been set out in our previous investigation (Mizuguchi, Sato, Uta & Sato, 2007). We have been so far involved in the structure of a methanol-solvated azo-iron complex with the ammonium cation (Mizuguchi, Sato & Uta, 2007) and also of an acetone-solvated one (Mizuguchi, Uta & Sato, 2007). In the present investigation, the same azo-FeIII complex but with a different cation (i.e. sodium cation) is used in place of the ammonium one. The ammonium salt is more widely used in practice as compared with the sodium one, because of its stable operation against temperature and humidity. To clarify this, the present structure analysis has been undertaken.

In the title compound, (I), there found two intramolecular hydrogen bonds, N3—H3N···O2 and N4—H4N···O1, between the NH group and the carbonyl O atom (Fig. 1 and Table 2). The sodium cation is found to form a dimer with another sodium one (Fig. 2), where each sodium cation is coordinated by five ligands: O5, O7, O8, O5i and O6ii [symmetry code: (i) -x, 1 - y, 1 - z; (ii) 1 - x, 1 - y, 1 - z]. Atoms Na1, O5, O7 and O8 are on the plane as characterized by the mean deviation of 0.0243 Å from the plane. It is interesting to note that each sodium cation unites three different anion complexes through the carbonyl O atoms: O5, O5i and O6ii. This indicates that compound (I) forms a quasi two-dimensional network parallel to the (001) plane. This kind of the sheet-like network has not been observed in our methanol and acetone-solvated azo-Fe complexes with the ammonium cation (Mizuguchi, Sato & Uta, 2007;

Mizuguchi, Uta & Sato, 2007). Then, it is highly expected that the charge-control characteristics can greatly be affected by the species of cations. Correlation between structure and charge-control ability is now under investigation and will be shortly reported elsewhere.

Related literature top

Two related structural studies of azo–Fe anion complexes with a different cation (i.e. ammonium cation) have been reported: a methanol-solvated complex (Mizuguchi, Sato & Uta, 2007) and an acetone-solvated one (Mizuguchi, Uta & Sato, 2007).

For related literature, see: Mizuguchi, Sato, Uta & Sato (2007); Tanaka (1995); Yasumatsu et al. (2006).

Experimental top

The title compound was prepared according to the methods previously reported (Yasumatsu et al., 2006). Single crystals of (I) were obtained from an acetone solution.

Refinement top

All H atoms were placed in geometrically idealized positions (C—H = 0.95 and 0.98 Å, and N—H = 0.88 Å) and constrained to ride on their parent atoms, with Uiso(H) = 1.2Ueq(parent atom).

Computing details top

Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC & Rigaku, 2006); program(s) used to solve structure: SIR2004 (Burla et al., 2003); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996); software used to prepare material for publication: CrystalStructure.

Figures top
[Figure 1] Fig. 1. The asymmetric unit of (I), showing 30% displacement ellipsoids. Dotted lines indicate intramolecular hydrogen bonds.
[Figure 2] Fig. 2. The sodium cation dimer with four acetone molecules. Each sodium cation is coordinated by five ligands. The atom Na1 unites three different azo-Fe anion-complexes through the carbonyl O atoms: O5, O5i and O6ii. [Symmetry codes: (i) -x, 1 - y, 1 - z; (ii) 1 - x, 1 - y, 1 - z; (iii) -1 + x, y, z].
Poly[bis(acetone)bis[µ-4-[(5-chloro-2-oxidophenyl)diazenyl]-3-oxido-N– phenylnaphthalene-2-carboxamidato]sodium(I)ferrate(III)] top
Crystal data top
[FeNa(C23H14ClN3O3)2(C3H6O)2]Z = 2
Mr = 1026.64F(000) = 1058.00
Triclinic, P1Dx = 1.431 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71075 Å
a = 13.8165 (4) ÅCell parameters from 21230 reflections
b = 13.8623 (4) Åθ = 3.1–30.0°
c = 14.1524 (5) ŵ = 0.50 mm−1
α = 98.8719 (10)°T = 93 K
β = 105.3882 (10)°Block, black
γ = 109.0641 (8)°0.18 × 0.10 × 0.10 mm
V = 2382.21 (13) Å3
Data collection top
Rigaku R-AXIS RAPID
diffractometer		9943 reflections with F2 > 2σ(F2)
Detector resolution: 10.00 pixels mm-1Rint = 0.043
ω scansθmax = 30.0°
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)		h = −19→19
Tmin = 0.918, Tmax = 0.951k = −18→19
29200 measured reflectionsl = −19→19
13791 independent reflections
Refinement top
Refinement on F20 restraints
R[F2 > 2σ(F2)] = 0.056H-atom parameters constrained
wR(F2) = 0.163 w = 1/[σ2(Fo2) + (0.0899P)2 + 0.6174P]
where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max < 0.001
13791 reflectionsΔρmax = 0.67 e Å−3
631 parametersΔρmin = −0.66 e Å−3
Crystal data top
[FeNa(C23H14ClN3O3)2(C3H6O)2]γ = 109.0641 (8)°
Mr = 1026.64V = 2382.21 (13) Å3
Triclinic, P1Z = 2
a = 13.8165 (4) ÅMo Kα radiation
b = 13.8623 (4) ŵ = 0.50 mm−1
c = 14.1524 (5) ÅT = 93 K
α = 98.8719 (10)°0.18 × 0.10 × 0.10 mm
β = 105.3882 (10)°
Data collection top
Rigaku R-AXIS RAPID
diffractometer		13791 independent reflections
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)		9943 reflections with F2 > 2σ(F2)
Tmin = 0.918, Tmax = 0.951Rint = 0.043
29200 measured reflectionsθmax = 30.0°
Refinement top
R[F2 > 2σ(F2)] = 0.056H-atom parameters constrained
wR(F2) = 0.163Δρmax = 0.67 e Å−3
S = 1.05Δρmin = −0.66 e Å−3
13791 reflectionsAbsolute structure: ?
631 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
Fe10.31606 (2)0.16230 (2)0.47513 (2)0.01612 (8)
Cl10.38547 (5)−0.07025 (5)0.04068 (4)0.03048 (14)
Cl20.19145 (5)0.04986 (5)0.89961 (5)0.02991 (14)
Na10.13517 (8)0.58239 (7)0.51452 (7)0.0225 (2)
O10.44066 (13)0.30060 (12)0.51878 (12)0.0196 (3)
O20.22198 (13)0.24151 (13)0.44431 (12)0.0202 (3)
O30.40711 (13)0.08387 (13)0.45764 (12)0.0210 (3)
O40.19287 (13)0.04703 (13)0.48461 (12)0.0227 (3)
O50.02589 (13)0.40350 (12)0.47922 (12)0.0201 (3)
O60.72706 (13)0.48182 (13)0.48145 (13)0.0243 (3)
O70.23557 (17)0.68164 (16)0.67806 (15)0.0382 (4)
O80.14432 (15)0.67557 (15)0.39620 (16)0.0333 (4)
N10.20889 (15)0.14164 (15)0.24167 (14)0.0179 (3)
N20.45392 (15)0.23816 (15)0.70695 (14)0.0187 (3)
N30.10993 (16)0.30301 (15)0.55036 (15)0.0200 (3)
N40.54202 (16)0.42610 (16)0.42128 (15)0.0230 (4)
N50.27647 (15)0.12597 (14)0.31353 (14)0.0170 (3)
N70.36381 (15)0.18355 (14)0.63488 (14)0.0176 (3)
C10.53196 (18)0.33593 (17)0.59485 (17)0.0176 (4)
C20.53897 (18)0.30636 (17)0.68714 (17)0.0185 (4)
C30.63941 (18)0.35065 (18)0.77251 (17)0.0206 (4)
C40.64824 (19)0.32463 (19)0.86600 (18)0.0227 (4)
C50.7462 (2)0.3664 (2)0.94388 (19)0.0276 (5)
C60.8399 (2)0.4360 (2)0.93258 (19)0.0291 (5)
C70.8337 (2)0.4644 (2)0.8437 (2)0.0277 (5)
C80.73351 (19)0.42249 (19)0.76142 (18)0.0229 (4)
C90.72539 (19)0.44944 (19)0.66820 (18)0.0215 (4)
C100.63053 (18)0.40934 (18)0.58666 (18)0.0200 (4)
C110.63754 (19)0.44278 (18)0.49172 (18)0.0202 (4)
C120.5242 (2)0.44629 (19)0.32462 (18)0.0224 (4)
C130.6035 (2)0.5190 (2)0.2988 (2)0.0259 (4)
C140.5776 (2)0.5339 (2)0.2018 (2)0.0315 (5)
C150.4748 (2)0.4791 (2)0.1311 (2)0.0345 (6)
C160.3955 (2)0.4077 (2)0.1567 (2)0.0339 (5)
C170.4192 (2)0.3912 (2)0.2527 (2)0.0280 (5)
C180.15271 (18)0.24337 (17)0.36269 (17)0.0182 (4)
C190.14686 (18)0.19647 (17)0.26329 (16)0.0177 (4)
C200.06999 (17)0.20183 (17)0.17447 (17)0.0185 (4)
C210.0596 (2)0.1544 (2)0.07434 (17)0.0238 (4)
C22−0.0169 (2)0.1596 (2)−0.00840 (18)0.0263 (5)
C23−0.0858 (2)0.2119 (2)0.00479 (19)0.0280 (5)
C24−0.07693 (19)0.2589 (2)0.10065 (18)0.0238 (4)
C250.00035 (19)0.25475 (18)0.18712 (17)0.0201 (4)
C260.00764 (18)0.30062 (17)0.28715 (17)0.0191 (4)
C270.07859 (18)0.29493 (17)0.37230 (16)0.0172 (4)
C280.07078 (17)0.33964 (17)0.47220 (17)0.0177 (4)
C290.11155 (19)0.32857 (19)0.65212 (17)0.0212 (4)
C300.1169 (2)0.4258 (2)0.70109 (19)0.0285 (5)
C310.1244 (2)0.4459 (2)0.80263 (19)0.0327 (5)
C320.1279 (2)0.3701 (2)0.8558 (2)0.0325 (5)
C330.1233 (2)0.2736 (2)0.8072 (2)0.0340 (6)
C340.1134 (2)0.2520 (2)0.70495 (19)0.0281 (5)
C350.19117 (19)0.04498 (18)0.57723 (17)0.0208 (4)
C360.1017 (2)−0.02391 (19)0.59606 (19)0.0235 (4)
C370.1024 (2)−0.02095 (19)0.69418 (19)0.0254 (4)
C380.1935 (2)0.04924 (19)0.77662 (18)0.0221 (4)
C390.28331 (19)0.11807 (18)0.76252 (17)0.0206 (4)
C400.28146 (18)0.11585 (17)0.66251 (17)0.0191 (4)
C410.40286 (18)0.04753 (18)0.36382 (16)0.0185 (4)
C420.33457 (18)0.06816 (17)0.28179 (16)0.0177 (4)
C430.32719 (19)0.03125 (18)0.18136 (17)0.0210 (4)
C440.38792 (19)−0.02652 (19)0.16375 (17)0.0218 (4)
C450.45506 (19)−0.04928 (18)0.24313 (18)0.0210 (4)
C460.46185 (18)−0.01315 (18)0.34240 (17)0.0205 (4)
C470.3919 (3)0.7379 (2)0.8251 (2)0.0517 (9)
C480.3028 (2)0.7536 (2)0.75075 (19)0.0278 (5)
C490.2974 (2)0.8606 (2)0.7686 (2)0.0349 (6)
C500.3021 (2)0.8333 (2)0.4768 (2)0.0341 (6)
C510.2019 (2)0.7614 (2)0.3904 (2)0.0274 (5)
C520.1753 (2)0.7969 (2)0.2955 (2)0.0398 (6)
H3N0.13860.25670.53660.024*
H40.58580.27780.87520.027*
H4N0.48350.39930.43760.028*
H50.75080.34791.00640.033*
H60.90740.46340.98680.035*
H70.89690.51260.83680.033*
H90.78870.49770.66160.026*
H130.67430.55770.34700.031*
H140.63170.58270.18390.038*
H150.45840.49020.06510.041*
H160.32470.36990.10810.041*
H170.36440.34270.27000.034*
H20−0.02290.1273−0.07510.032*
H210.10560.11870.06390.029*
H23−0.13840.2146−0.05260.034*
H24−0.12310.29490.10950.029*
H26−0.03870.33670.29520.023*
H300.11540.47830.66550.034*
H310.12720.51220.83600.039*
H320.13350.38470.92530.039*
H330.12680.22200.84360.041*
H340.10790.18470.67110.034*
H360.0404−0.07290.54060.028*
H370.0410−0.06660.70580.030*
H390.34460.16560.81890.025*
H430.28160.04560.12690.025*
H450.4959−0.08950.22870.025*
H460.5065−0.02950.39600.025*
H47a0.36740.71530.88000.062*
H47b0.45590.80450.85360.062*
H47c0.41090.68340.79060.062*
H49a0.33990.90370.73370.042*
H49b0.32730.89520.84160.042*
H49c0.22150.85320.74210.042*
H50a0.35560.87550.45030.041*
H50b0.33300.79100.51530.041*
H50c0.28360.88050.52150.041*
H52a0.21090.77330.25050.048*
H52b0.20120.87420.31300.048*
H53c0.09630.76620.26070.048*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Fe10.01826 (16)0.02073 (16)0.01130 (14)0.00860 (13)0.00639 (11)0.00470 (11)
Cl10.0409 (3)0.0459 (3)0.0157 (2)0.0273 (3)0.0143 (2)0.0073 (2)
Cl20.0375 (3)0.0376 (3)0.0227 (2)0.0147 (2)0.0183 (2)0.0152 (2)
Na10.0227 (4)0.0219 (4)0.0250 (4)0.0087 (4)0.0112 (3)0.0062 (3)
O10.0194 (7)0.0231 (7)0.0176 (7)0.0082 (6)0.0065 (6)0.0080 (6)
O20.0217 (7)0.0271 (8)0.0128 (7)0.0122 (6)0.0050 (5)0.0036 (6)
O30.0267 (8)0.0287 (8)0.0120 (6)0.0155 (7)0.0075 (6)0.0051 (6)
O40.0227 (8)0.0248 (8)0.0162 (7)0.0045 (7)0.0060 (6)0.0041 (6)
O50.0208 (7)0.0213 (7)0.0206 (7)0.0101 (6)0.0087 (6)0.0044 (6)
O60.0218 (7)0.0284 (8)0.0273 (8)0.0098 (7)0.0140 (6)0.0099 (7)
O70.0369 (10)0.0368 (10)0.0290 (10)0.0089 (9)0.0065 (8)−0.0041 (8)
O80.0308 (9)0.0347 (10)0.0406 (11)0.0123 (8)0.0173 (8)0.0186 (8)
N10.0190 (8)0.0232 (9)0.0143 (8)0.0096 (7)0.0067 (6)0.0068 (7)
N20.0182 (8)0.0221 (9)0.0169 (8)0.0086 (7)0.0071 (7)0.0049 (7)
N30.0246 (9)0.0213 (8)0.0182 (8)0.0112 (8)0.0105 (7)0.0055 (7)
N40.0229 (9)0.0293 (10)0.0219 (9)0.0100 (8)0.0124 (7)0.0118 (8)
N50.0191 (8)0.0194 (8)0.0155 (8)0.0093 (7)0.0075 (6)0.0066 (6)
N70.0201 (8)0.0195 (8)0.0167 (8)0.0090 (7)0.0092 (7)0.0056 (7)
C10.0194 (9)0.0192 (9)0.0171 (9)0.0090 (8)0.0093 (8)0.0037 (7)
C20.0183 (9)0.0201 (10)0.0170 (9)0.0074 (8)0.0063 (8)0.0043 (8)
C30.0205 (10)0.0235 (10)0.0187 (10)0.0099 (9)0.0077 (8)0.0037 (8)
C40.0218 (10)0.0246 (11)0.0206 (10)0.0084 (9)0.0065 (8)0.0054 (8)
C50.0276 (12)0.0354 (13)0.0172 (10)0.0122 (11)0.0043 (9)0.0055 (9)
C60.0210 (11)0.0396 (14)0.0200 (11)0.0103 (11)0.0016 (9)0.0023 (10)
C70.0216 (11)0.0305 (12)0.0258 (12)0.0065 (10)0.0063 (9)0.0034 (9)
C80.0212 (10)0.0269 (11)0.0198 (10)0.0087 (9)0.0080 (8)0.0037 (8)
C90.0185 (10)0.0239 (10)0.0226 (10)0.0069 (9)0.0090 (8)0.0067 (8)
C100.0192 (10)0.0220 (10)0.0207 (10)0.0087 (9)0.0086 (8)0.0057 (8)
C110.0217 (10)0.0205 (10)0.0207 (10)0.0077 (9)0.0108 (8)0.0059 (8)
C120.0282 (11)0.0260 (11)0.0229 (11)0.0155 (10)0.0148 (9)0.0116 (9)
C130.0292 (12)0.0289 (11)0.0264 (11)0.0129 (10)0.0151 (9)0.0124 (9)
C140.0387 (14)0.0378 (14)0.0341 (14)0.0209 (12)0.0240 (11)0.0200 (11)
C150.0493 (16)0.0487 (16)0.0247 (12)0.0308 (14)0.0219 (11)0.0198 (11)
C160.0372 (14)0.0440 (15)0.0238 (12)0.0188 (13)0.0101 (10)0.0116 (11)
C170.0295 (12)0.0321 (12)0.0276 (12)0.0131 (11)0.0130 (10)0.0138 (10)
C180.0187 (9)0.0182 (9)0.0167 (9)0.0047 (8)0.0073 (8)0.0054 (7)
C190.0203 (10)0.0209 (10)0.0147 (9)0.0097 (9)0.0073 (7)0.0056 (7)
C200.0169 (9)0.0219 (10)0.0164 (9)0.0055 (9)0.0067 (7)0.0068 (8)
C210.0257 (11)0.0352 (12)0.0163 (10)0.0162 (10)0.0095 (8)0.0082 (9)
C220.0292 (12)0.0372 (13)0.0142 (10)0.0149 (11)0.0074 (9)0.0065 (9)
C230.0296 (12)0.0377 (13)0.0181 (10)0.0159 (11)0.0052 (9)0.0095 (10)
C240.0238 (11)0.0311 (12)0.0209 (10)0.0156 (10)0.0065 (8)0.0092 (9)
C250.0225 (10)0.0237 (10)0.0162 (9)0.0095 (9)0.0081 (8)0.0066 (8)
C260.0203 (10)0.0208 (10)0.0186 (10)0.0092 (9)0.0081 (8)0.0059 (8)
C270.0186 (9)0.0179 (9)0.0157 (9)0.0064 (8)0.0077 (7)0.0043 (7)
C280.0171 (9)0.0164 (9)0.0171 (9)0.0035 (8)0.0068 (7)0.0027 (7)
C290.0217 (10)0.0267 (11)0.0175 (10)0.0102 (9)0.0097 (8)0.0053 (8)
C300.0406 (14)0.0240 (11)0.0199 (11)0.0116 (11)0.0103 (10)0.0044 (9)
C310.0461 (15)0.0334 (13)0.0186 (11)0.0168 (12)0.0114 (10)0.0028 (10)
C320.0454 (15)0.0415 (14)0.0183 (11)0.0216 (13)0.0157 (10)0.0099 (10)
C330.0538 (17)0.0433 (15)0.0251 (12)0.0317 (14)0.0232 (12)0.0187 (11)
C340.0426 (14)0.0325 (12)0.0223 (11)0.0241 (12)0.0169 (10)0.0113 (9)
C350.0229 (10)0.0231 (10)0.0194 (10)0.0112 (9)0.0075 (8)0.0081 (8)
C360.0227 (11)0.0235 (11)0.0222 (11)0.0065 (9)0.0069 (8)0.0065 (9)
C370.0252 (11)0.0250 (11)0.0275 (12)0.0073 (10)0.0123 (9)0.0101 (9)
C380.0283 (11)0.0266 (11)0.0186 (10)0.0134 (10)0.0124 (9)0.0110 (8)
C390.0212 (10)0.0234 (10)0.0171 (10)0.0074 (9)0.0079 (8)0.0056 (8)
C400.0217 (10)0.0211 (10)0.0186 (10)0.0096 (9)0.0097 (8)0.0084 (8)
C410.0224 (10)0.0230 (10)0.0124 (9)0.0104 (9)0.0069 (7)0.0054 (8)
C420.0209 (10)0.0210 (10)0.0139 (9)0.0097 (9)0.0075 (7)0.0055 (7)
C430.0239 (10)0.0276 (11)0.0146 (9)0.0124 (9)0.0077 (8)0.0065 (8)
C440.0268 (11)0.0285 (11)0.0127 (9)0.0122 (10)0.0093 (8)0.0043 (8)
C450.0244 (10)0.0239 (10)0.0188 (10)0.0123 (9)0.0099 (8)0.0056 (8)
C460.0221 (10)0.0250 (10)0.0164 (10)0.0114 (9)0.0066 (8)0.0055 (8)
C470.062 (2)0.059 (2)0.0353 (16)0.0415 (18)0.0037 (15)−0.0011 (14)
C480.0294 (12)0.0326 (12)0.0238 (11)0.0119 (11)0.0139 (9)0.0057 (10)
C490.0408 (15)0.0336 (13)0.0343 (14)0.0170 (12)0.0150 (12)0.0101 (11)
C500.0413 (15)0.0314 (13)0.0290 (13)0.0100 (12)0.0135 (11)0.0119 (10)
C510.0278 (12)0.0294 (12)0.0328 (13)0.0141 (11)0.0164 (10)0.0115 (10)
C520.0360 (15)0.0411 (15)0.0366 (15)0.0070 (13)0.0073 (12)0.0204 (13)
Geometric parameters (Å, °) top
Fe1—O11.9837 (13)C18—C271.449 (3)
Fe1—O21.966 (2)C19—C201.444 (3)
Fe1—O31.950 (2)C20—C211.416 (3)
Fe1—O41.9695 (16)C20—C251.417 (4)
Fe1—N52.1411 (19)C21—C221.383 (3)
Fe1—N72.1236 (19)C21—H210.950
Cl1—C441.741 (2)C22—C231.404 (4)
Cl2—C381.747 (2)C22—H200.950
Na1—O52.3346 (16)C23—C241.366 (3)
Na1—O5i2.320 (2)C23—H230.950
Na1—O6ii2.342 (2)C24—C251.418 (3)
Na1—O72.2894 (19)C24—H240.950
Na1—O82.272 (2)C25—C261.422 (3)
O1—C11.305 (2)C26—C271.368 (3)
O2—C181.300 (2)C26—H260.950
O3—C411.324 (2)C27—C281.500 (3)
O4—C351.322 (3)C29—C301.386 (3)
O5—C281.242 (3)C29—C341.392 (4)
O6—C111.235 (3)C30—C311.390 (3)
O7—C481.220 (2)C30—H300.950
O8—C511.226 (3)C31—C321.389 (4)
N1—N51.285 (2)C31—H310.950
N1—C191.378 (3)C32—C331.380 (4)
N2—N71.279 (2)C32—H320.950
N2—C21.373 (3)C33—C341.392 (4)
N3—C281.345 (3)C33—H330.950
N3—C291.421 (3)C34—H340.950
N3—H3N0.880C35—C361.412 (3)
N4—C111.349 (3)C35—C401.419 (2)
N4—C121.412 (3)C36—C371.380 (3)
N4—H4N0.880C36—H360.950
N5—C421.410 (3)C37—C381.401 (2)
N7—C401.407 (3)C37—H370.950
C1—C21.417 (3)C38—C391.381 (3)
C1—C101.456 (3)C39—C401.404 (3)
C2—C31.445 (2)C39—H390.950
C3—C41.409 (3)C41—C421.420 (3)
C3—C81.420 (3)C41—C461.401 (4)
C4—C51.372 (3)C42—C431.399 (3)
C4—H40.950C43—C441.377 (4)
C5—C61.405 (3)C43—H430.950
C5—H50.950C44—C451.403 (3)
C6—C71.364 (4)C45—C461.384 (3)
C6—H60.950C45—H450.950
C7—C81.421 (3)C46—H460.950
C7—H70.950C47—C481.493 (4)
C8—C91.412 (3)C47—H47a0.980
C9—C101.372 (2)C47—H47b0.980
C9—H90.950C47—H47c0.980
C10—C111.504 (3)C48—C491.496 (4)
C12—C131.398 (3)C49—H49a0.980
C12—C171.406 (3)C49—H49b0.980
C13—C141.389 (4)C49—H49c0.980
C13—H130.950C50—C511.493 (3)
C14—C151.379 (3)C50—H50a0.980
C14—H140.950C50—H50b0.980
C15—C161.388 (4)C50—H50c0.980
C15—H150.950C51—C521.497 (4)
C16—C171.383 (4)C52—H52a0.980
C16—H160.950C52—H52b0.980
C17—H170.950C52—H53c0.980
C18—C191.425 (3)
Na1···Na1i3.5581 (13)N2···H45iv2.595
Cl1···H49biii2.635C6···H32vi2.797
O3···H46iv2.458C18···H37vii2.778
O3···H50av2.718C46···H50av2.703
O1—Fe1—O286.60 (7)C20—C21—C22120.5 (2)
O1—Fe1—O392.44 (7)C20—C21—H21119.7
O1—Fe1—O4157.75 (7)C22—C21—H21119.8
O1—Fe1—N5101.35 (6)C21—C22—C23121.0 (2)
O1—Fe1—N780.70 (6)C21—C22—H20119.5
O2—Fe1—O3160.13 (7)C23—C22—H20119.5
O2—Fe1—O489.25 (7)C22—C23—C24119.6 (2)
O2—Fe1—N581.27 (7)C22—C23—H23120.2
O2—Fe1—N7105.83 (8)C24—C23—H23120.2
O3—Fe1—O498.69 (7)C23—C24—C25120.9 (2)
O3—Fe1—N579.47 (7)C23—C24—H24119.6
O3—Fe1—N793.57 (8)C25—C24—H24119.6
O4—Fe1—N599.60 (6)C20—C25—C24119.8 (2)
O4—Fe1—N779.44 (6)C20—C25—C26119.0 (2)
N5—Fe1—N7172.78 (8)C24—C25—C26121.1 (2)
O5—Na1—O5i80.28 (6)C25—C26—C27122.7 (2)
O5—Na1—O6ii83.32 (7)C25—C26—H26118.6
O5—Na1—O7121.07 (8)C27—C26—H26118.6
O5—Na1—O8124.62 (6)C18—C27—C26120.0 (2)
O5i—Na1—O6ii162.26 (7)C18—C27—C28123.4 (2)
O5i—Na1—O794.92 (8)C26—C27—C28116.5 (2)
O5i—Na1—O892.23 (8)O5—C28—N3123.0 (2)
O6ii—Na1—O787.74 (8)O5—C28—C27120.5 (2)
O6ii—Na1—O8102.69 (8)N3—C28—C27116.4 (2)
O7—Na1—O8114.20 (7)N3—C29—C30123.6 (2)
Fe1—O1—C1129.50 (16)N3—C29—C34116.6 (2)
Fe1—O2—C18135.37 (16)C30—C29—C34119.7 (2)
Fe1—O3—C41117.35 (16)C29—C30—C31119.6 (2)
Fe1—O4—C35116.21 (11)C29—C30—H30120.2
Na1—O5—Na1i99.72 (8)C31—C30—H30120.2
Na1—O5—C28116.87 (13)C30—C31—C32120.7 (2)
Na1i—O5—C28143.08 (14)C30—C31—H31119.6
Na1ii—O6—C11131.51 (18)C32—C31—H31119.6
Na1—O7—C48161.6 (2)C31—C32—C33119.7 (2)
Na1—O8—C51138.02 (17)C31—C32—H32120.2
N5—N1—C19120.6 (2)C33—C32—H32120.2
N7—N2—C2119.9 (2)C32—C33—C34120.0 (3)
C28—N3—C29129.1 (2)C32—C33—H33120.0
C28—N3—H3N115.5C34—C33—H33120.0
C29—N3—H3N115.5C29—C34—C33120.3 (2)
C11—N4—C12128.1 (2)C29—C34—H34119.9
C11—N4—H4N115.9C33—C34—H34119.9
C12—N4—H4N115.9O4—C35—C36122.86 (17)
Fe1—N5—N1133.58 (18)O4—C35—C40119.5 (2)
Fe1—N5—C42111.06 (14)C36—C35—C40117.6 (2)
N1—N5—C42115.27 (19)C35—C36—C37120.76 (18)
Fe1—N7—N2132.41 (17)C35—C36—H36119.6
Fe1—N7—C40111.44 (11)C37—C36—H36119.6
N2—N7—C40115.84 (19)C36—C37—C38120.1 (2)
O1—C1—C2122.2 (2)C36—C37—H37120.0
O1—C1—C10119.8 (2)C38—C37—H37120.0
C2—C1—C10117.99 (18)Cl2—C38—C37118.6 (2)
N2—C2—C1125.19 (18)Cl2—C38—C39119.82 (15)
N2—C2—C3113.3 (2)C37—C38—C39121.5 (2)
C1—C2—C3121.4 (2)C38—C39—C40118.12 (17)
C2—C3—C4122.7 (2)C38—C39—H39120.9
C2—C3—C8118.7 (2)C40—C39—H39120.9
C4—C3—C8118.60 (18)N7—C40—C35112.7 (2)
C3—C4—C5120.6 (2)N7—C40—C39125.32 (16)
C3—C4—H4119.7C35—C40—C39121.9 (2)
C5—C4—H4119.7O3—C41—C42119.3 (2)
C4—C5—C6121.0 (2)O3—C41—C46122.0 (2)
C4—C5—H5119.5C42—C41—C46118.7 (2)
C6—C5—H5119.5N5—C42—C41112.8 (2)
C5—C6—C7119.9 (2)N5—C42—C43125.8 (2)
C5—C6—H6120.0C41—C42—C43121.4 (2)
C7—C6—H6120.0C42—C43—C44118.1 (2)
C6—C7—C8120.5 (2)C42—C43—H43121.0
C6—C7—H7119.7C44—C43—H43121.0
C8—C7—H7119.7Cl1—C44—C43119.91 (19)
C3—C8—C7119.4 (2)Cl1—C44—C45118.3 (2)
C3—C8—C9119.03 (19)C43—C44—C45121.8 (2)
C7—C8—C9121.6 (2)C44—C45—C46120.1 (2)
C8—C9—C10123.2 (2)C44—C45—H45120.0
C8—C9—H9118.4C46—C45—H45120.0
C10—C9—H9118.4C41—C46—C45120.0 (2)
C1—C10—C9119.6 (2)C41—C46—H46120.0
C1—C10—C11124.15 (18)C45—C46—H46120.0
C9—C10—C11116.2 (2)C48—C47—H47a109.5
O6—C11—N4124.0 (2)C48—C47—H47b109.5
O6—C11—C10120.0 (2)C48—C47—H47c109.5
N4—C11—C10116.0 (2)H47a—C47—H47b109.5
N4—C12—C13123.72 (19)H47a—C47—H47c109.5
N4—C12—C17116.9 (2)H47b—C47—H47c109.5
C13—C12—C17119.4 (2)O7—C48—C47121.5 (2)
C12—C13—C14119.4 (2)O7—C48—C49120.6 (2)
C12—C13—H13120.3C47—C48—C49117.9 (2)
C14—C13—H13120.3C48—C49—H49a109.5
C13—C14—C15121.1 (2)C48—C49—H49b109.5
C13—C14—H14119.5C48—C49—H49c109.5
C15—C14—H14119.5H49a—C49—H49b109.5
C14—C15—C16119.8 (2)H49a—C49—H49c109.5
C14—C15—H15120.1H49b—C49—H49c109.5
C16—C15—H15120.1C51—C50—H50a109.5
C15—C16—C17120.3 (2)C51—C50—H50b109.5
C15—C16—H16119.9C51—C50—H50c109.5
C17—C16—H16119.9H50a—C50—H50b109.5
C12—C17—C16120.1 (2)H50a—C50—H50c109.5
C12—C17—H17120.0H50b—C50—H50c109.5
C16—C17—H17120.0O8—C51—C50121.3 (2)
O2—C18—C19122.3 (2)O8—C51—C52121.0 (2)
O2—C18—C27119.3 (2)C50—C51—C52117.7 (2)
C19—C18—C27118.4 (2)C51—C52—H52a109.5
N1—C19—C18125.3 (2)C51—C52—H52b109.5
N1—C19—C20114.0 (2)C51—C52—H53c109.5
C18—C19—C20120.6 (2)H52a—C52—H52b109.5
C19—C20—C21122.6 (2)H52a—C52—H53c109.5
C19—C20—C25119.2 (2)H52b—C52—H53c109.5
C21—C20—C25118.2 (2)
O1—Fe1—O2—C18116.7 (2)O1—C1—C2—N20.9 (4)
O2—Fe1—O1—C1141.4 (2)O1—C1—C2—C3−176.6 (2)
O1—Fe1—O3—C41−101.36 (15)O1—C1—C10—C9177.5 (2)
O3—Fe1—O1—C1−58.5 (2)O1—C1—C10—C11−4.7 (4)
O1—Fe1—O4—C35−19.9 (3)C2—C1—C10—C9−1.7 (3)
O4—Fe1—O1—C161.8 (3)C2—C1—C10—C11176.1 (2)
O1—Fe1—N5—N1−93.59 (19)C10—C1—C2—N2−179.95 (19)
O1—Fe1—N5—C4290.08 (14)C10—C1—C2—C32.6 (3)
N5—Fe1—O1—C1−138.2 (2)N2—C2—C3—C40.7 (3)
O1—Fe1—N7—N2−23.2 (2)N2—C2—C3—C8180.0 (2)
O1—Fe1—N7—C40163.59 (18)C1—C2—C3—C4178.5 (2)
N7—Fe1—O1—C134.8 (2)C1—C2—C3—C8−2.2 (4)
O2—Fe1—O3—C41−14.6 (2)C2—C3—C4—C5178.1 (2)
O3—Fe1—O2—C1828.9 (3)C2—C3—C8—C7−178.2 (2)
O2—Fe1—O4—C35−99.02 (19)C2—C3—C8—C91.0 (4)
O4—Fe1—O2—C18−85.2 (2)C4—C3—C8—C71.1 (4)
O2—Fe1—N5—N1−8.87 (18)C4—C3—C8—C9−179.7 (2)
O2—Fe1—N5—C42174.80 (14)C8—C3—C4—C5−1.2 (4)
N5—Fe1—O2—C1814.6 (2)C3—C4—C5—C60.1 (3)
O2—Fe1—N7—N2−106.9 (2)C4—C5—C6—C71.1 (4)
O2—Fe1—N7—C4079.84 (17)C5—C6—C7—C8−1.2 (4)
N7—Fe1—O2—C18−164.0 (2)C6—C7—C8—C30.1 (3)
O3—Fe1—O4—C3599.27 (19)C6—C7—C8—C9−179.1 (2)
O4—Fe1—O3—C4197.97 (15)C3—C8—C9—C10−0.2 (4)
O3—Fe1—N5—N1176.02 (19)C7—C8—C9—C10179.0 (2)
O3—Fe1—N5—C42−0.31 (13)C8—C9—C10—C10.5 (4)
N5—Fe1—O3—C41−0.26 (14)C8—C9—C10—C11−177.4 (2)
O3—Fe1—N7—N268.7 (2)C1—C10—C11—O6−161.0 (2)
O3—Fe1—N7—C40−104.53 (17)C1—C10—C11—N418.2 (3)
N7—Fe1—O3—C41177.82 (14)C9—C10—C11—O616.8 (3)
O4—Fe1—N5—N178.87 (19)C9—C10—C11—N4−163.9 (2)
O4—Fe1—N5—C42−97.46 (14)N4—C12—C13—C14−179.4 (2)
N5—Fe1—O4—C35179.97 (14)N4—C12—C17—C16179.5 (2)
O4—Fe1—N7—N2166.9 (2)C13—C12—C17—C161.2 (4)
O4—Fe1—N7—C40−6.34 (17)C17—C12—C13—C14−1.3 (4)
N7—Fe1—O4—C357.23 (19)C12—C13—C14—C150.7 (5)
O5—Na1—O5i—C28i−172.4 (2)C13—C14—C15—C16−0.1 (4)
O5i—Na1—O5—C28−174.88 (17)C14—C15—C16—C17−0.0 (4)
O5—Na1—O6ii—C11ii158.7 (2)C15—C16—C17—C12−0.5 (5)
O6ii—Na1—O5—Na1i173.20 (7)O2—C18—C19—N12.5 (3)
O6ii—Na1—O5—C28−1.68 (17)O2—C18—C19—C20−178.92 (19)
O5—Na1—O7—C48165.7 (7)O2—C18—C27—C26177.85 (19)
O7—Na1—O5—Na1i89.91 (11)O2—C18—C27—C28−5.0 (3)
O7—Na1—O5—C28−84.96 (19)C19—C18—C27—C26−2.0 (3)
O5—Na1—O8—C51−167.7 (3)C19—C18—C27—C28175.07 (19)
O8—Na1—O5—Na1i−85.97 (11)C27—C18—C19—N1−177.63 (19)
O8—Na1—O5—C2899.15 (18)C27—C18—C19—C201.0 (3)
O5i—Na1—O6ii—C11ii−178.8 (2)N1—C19—C20—C210.2 (3)
O6ii—Na1—O5i—Na1i−22.7 (2)N1—C19—C20—C25178.98 (19)
O6ii—Na1—O5i—C28i164.9 (2)C18—C19—C20—C21−178.5 (2)
O5i—Na1—O7—C48−112.7 (7)C18—C19—C20—C250.2 (3)
O7—Na1—O5i—Na1i−120.71 (8)C19—C20—C21—C22178.5 (2)
O7—Na1—O5i—C28i66.9 (2)C19—C20—C25—C24−178.8 (2)
O5i—Na1—O8—C51112.6 (3)C19—C20—C25—C26−0.4 (3)
O8—Na1—O5i—Na1i124.76 (7)C21—C20—C25—C240.0 (2)
O8—Na1—O5i—C28i−47.6 (2)C21—C20—C25—C26178.4 (2)
O6ii—Na1—O7—C4884.9 (7)C25—C20—C21—C22−0.2 (3)
O7—Na1—O6ii—C11ii−79.6 (2)C20—C21—C22—C230.0 (2)
O6ii—Na1—O8—C51−77.1 (3)C21—C22—C23—C240.4 (3)
O8—Na1—O6ii—C11ii34.7 (2)C22—C23—C24—C25−0.6 (3)
O7—Na1—O8—C5116.2 (3)C23—C24—C25—C200.4 (3)
O8—Na1—O7—C48−18.0 (8)C23—C24—C25—C26−178.0 (2)
Fe1—O1—C1—C2−32.1 (3)C20—C25—C26—C27−0.7 (3)
Fe1—O1—C1—C10148.77 (19)C24—C25—C26—C27177.7 (2)
Fe1—O2—C18—C19−14.7 (3)C25—C26—C27—C182.0 (3)
Fe1—O2—C18—C27165.40 (15)C25—C26—C27—C28−175.36 (19)
Fe1—O3—C41—C420.8 (2)C18—C27—C28—O5163.18 (19)
Fe1—O3—C41—C46−177.58 (15)C18—C27—C28—N3−19.8 (2)
Fe1—O4—C35—C36171.6 (2)C26—C27—C28—O5−19.6 (2)
Fe1—O4—C35—C40−7.1 (3)C26—C27—C28—N3157.38 (19)
Na1—O5—C28—N395.0 (2)N3—C29—C30—C31−176.3 (2)
Na1—O5—C28—C27−88.25 (17)N3—C29—C34—C33175.2 (2)
Na1i—O5—C28—N3−76.6 (2)C30—C29—C34—C33−1.6 (4)
Na1i—O5—C28—C27100.2 (2)C34—C29—C30—C310.2 (3)
Na1ii—O6—C11—N4−122.2 (2)C29—C30—C31—C320.7 (4)
Na1ii—O6—C11—C1057.0 (2)C30—C31—C32—C33−0.4 (4)
Na1—O7—C48—C47−116.2 (7)C31—C32—C33—C34−1.0 (4)
Na1—O7—C48—C4964.5 (8)C32—C33—C34—C292.0 (4)
Na1—O8—C51—C504.8 (5)O4—C35—C36—C37−178.0 (2)
Na1—O8—C51—C52−176.5 (2)O4—C35—C40—N71.2 (3)
N5—N1—C19—C182.4 (3)O4—C35—C40—C39179.1 (2)
N5—N1—C19—C20−176.30 (18)C36—C35—C40—N7−177.6 (2)
C19—N1—N5—Fe13.3 (2)C36—C35—C40—C390.3 (4)
C19—N1—N5—C42179.52 (18)C40—C35—C36—C370.7 (4)
N7—N2—C2—C110.7 (4)C35—C36—C37—C38−1.5 (4)
N7—N2—C2—C3−171.6 (2)C36—C37—C38—Cl2−179.6 (2)
C2—N2—N7—Fe17.0 (3)C36—C37—C38—C391.3 (4)
C2—N2—N7—C40179.96 (17)Cl2—C38—C39—C40−179.4 (2)
C28—N3—C29—C30−29.4 (3)C37—C38—C39—C40−0.3 (4)
C28—N3—C29—C34153.9 (2)C38—C39—C40—N7177.1 (2)
C29—N3—C28—O5−1.6 (3)C38—C39—C40—C35−0.5 (4)
C29—N3—C28—C27−178.50 (18)O3—C41—C42—N5−1.1 (2)
C11—N4—C12—C13−22.6 (4)O3—C41—C42—C43−179.87 (19)
C11—N4—C12—C17159.2 (2)O3—C41—C46—C45−179.87 (19)
C12—N4—C11—O61.5 (4)C42—C41—C46—C451.7 (3)
C12—N4—C11—C10−177.7 (2)C46—C41—C42—N5177.39 (18)
Fe1—N5—C42—C410.8 (2)C46—C41—C42—C43−1.4 (3)
Fe1—N5—C42—C43179.51 (17)N5—C42—C43—C44−178.3 (2)
N1—N5—C42—C41−176.27 (17)C41—C42—C43—C440.3 (3)
N1—N5—C42—C432.4 (3)C42—C43—C44—Cl1−177.69 (16)
Fe1—N7—C40—C354.6 (2)C42—C43—C44—C450.5 (3)
Fe1—N7—C40—C39−173.2 (2)Cl1—C44—C45—C46178.04 (17)
N2—N7—C40—C35−169.8 (2)C43—C44—C45—C46−0.2 (3)
N2—N7—C40—C3912.4 (3)C44—C45—C46—C41−0.9 (3)
Symmetry codes: (i) −x, −y+1, −z+1; (ii) −x+1, −y+1, −z+1; (iii) x, y−1, z−1; (iv) −x+1, −y, −z+1; (v) x, y−1, z; (vi) −x+1, −y+1, −z+2; (vii) −x, −y, −z+1.
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N3—H3N···O20.881.992.660 (3)132
N4—H4N···O10.881.962.658 (2)135
Table 1
Selected geometric parameters (Å, °) top
Fe1—O11.9837 (13)Na1—O52.3346 (16)
Fe1—O21.966 (2)Na1—O5i2.320 (2)
Fe1—O31.950 (2)Na1—O6ii2.342 (2)
Fe1—O41.9695 (16)Na1—O72.2894 (19)
Fe1—N52.1411 (19)Na1—O82.272 (2)
Fe1—N72.1236 (19)
Na1···Na1i3.5581 (13)
O1—Fe1—O286.60 (7)O3—Fe1—O498.69 (7)
O1—Fe1—O392.44 (7)O3—Fe1—N579.47 (7)
O1—Fe1—O4157.75 (7)O3—Fe1—N793.57 (8)
O1—Fe1—N5101.35 (6)O4—Fe1—N599.60 (6)
O1—Fe1—N780.70 (6)O4—Fe1—N779.44 (6)
O2—Fe1—O3160.13 (7)N5—Fe1—N7172.78 (8)
O2—Fe1—O489.25 (7)O5—Na1—O5i80.28 (6)
O2—Fe1—N581.27 (7)O5—Na1—O6ii83.32 (7)
O2—Fe1—N7105.83 (8)O5i—Na1—O6ii162.26 (7)
Symmetry codes: (i) −x, −y+1, −z+1; (ii) −x+1, −y+1, −z+1.
Table 2
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N3—H3N···O20.881.992.660 (3)132
N4—H4N···O10.881.962.658 (2)135
references
References top

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