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Acta Cryst. (2008). E64, m333-m334    [ doi:10.1107/S1600536808000433 ]

Poly[bis(acetone-[kappa]O)bis{[mu]3-1-[(5-chloro-2-oxidophenyl)diazenyl]-2-naphtholato-[kappa]4O:O,O':O'}sodium(I)chromium(III)\]

S. Ito, Y. Sato and J. Mizuguchi

Abstract top

The title compound, [CrNa(C16H9ClN2O2)2(C3H6O)2]n, is an azo-CrIII complex polymer that is used as a charge-control agent in electrophotography. The monomeric unit is composed of octahedral CrIII and NaI units, and is characterized by twofold rotation symmetry. The CrIII atom is chelated by two N and four O atoms from two [(5-chloro-2-oxidophenyl)diazenyl]-2-naphtholate ligands. The ligand anion exists in the cis form. The NaI atom is coordinated by two phenoxy O atoms from a neighboring CrIII unit, two naphthoxy O atoms from another neighboring CrIII unit and two O atoms from acetone molecules. The dinuclear complex forms a one-dimensional polymer running along the c axis.

Comment top

The title compound, (I), is an azo-Cr complex polymer 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 azo-Fe complex with an ammonium cation (Mizuguchi et al., 2007a) and its acetone solvate (Mizuguchi, Uta & Sato, 2007). Further structural analysis was carried out on the same azo-Fe complex but with a different cation, i.e. sodium one in place of the ammonium ion. The compound was recrystallized from an acetone (Mizuguchi et al., 2007b) or acetonitrile solution (Sato, Uta & Mizuguchi, 2007). The present paper reports an azo-Cr complex polymer whose monomeric unit comprises an octahedral CrIII unit and an octahedral NaI one.

Figure 1 shows the ORTEPIII plot (Burnett & Johnson, 1996) of the monomeric unit of (I). The unit is composed of an octahedral CrIII unit and an octahedral NaI one. The anion complex exists in cis-form, just as in the ordinary azo-Fe complexes described in the above paragraph. Each CrIII atom is chelated by the N and two O atoms from two [(5-chloro-2-oxidophenyl) diazenyl]-2-naphtholate ligands. On the other hand, the NaI cation coordinates to a phenoxy O atom from the two ligands of each octahedral CrIII unit, a naphthoxy O atom from the two ligands of each neighboring CrIII unit and two acetone molecules. The octahedral CrIII unit and the octahedral NaI one are repeated alternately to form a one dimensional polymer along c through the four O ligands in common (Fig. 2). The polymer formation contributes to a significant stabilization of (I) whose property is pre-requisite for the CCA application in electrophotography.

Related literature top

For general background to charge-control agents, see: Tanaka (1995). 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); Sato et al. (2008).

Experimental top

The title compound was prepared according to the previously reported method (Yasumatsu et al., 2006). Single crystals were recrystallized from an acetone solution. After 48 h, a number of single crystals were obtained in the form of blocks. Since the single crystals were found to include two solvent molecules according to the thermogravimetric analysis, reflection data were collected at 93 K.

Refinement top

All H atoms were placed in geometrically idealized positions (C—H = 0.93 or 0.96 Å) and constrained to ride on their parent atoms, with Uiso (H) = 1.2Ueq(C) or 1.5Ueq(methyl C). R-merge for the reflection data was 15.3%. This indicates poor crystal quality resulting in a rather high value of the R factor. The highest electron density (2.03 e Å-3) is located 0.64 Å from Cr1.

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, 2008); 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 monomeric structure of the title compound, showing 50% displacement ellipsoids. Unlabelled atoms except for C17—C19 and O3 are related to labelled atoms by the symmetry operation (x, 1/2 - y, 1/2 - z), whereas those for C17—C19 and O3 by the symmetry operation (x, 1/2 - y, -1/2 - z).
[Figure 2] Fig. 2. Polymeric structure of the title compound along the c axis.
Poly[bis(acetone)bis{µ3-1-[(5-chloro-2-oxidophenyl)diazenyl]-2- naphtholato-κ4O:O,O':O'}sodium(I)chromium(III)] top
Crystal data top
[CrNa(C16H9ClN2O2)2(C3H6O)2]F000 = 1612.00
Mr = 784.55Dx = 1.498 Mg m−3
Orthorhombic, PnnaMo Kα radiation
λ = 0.71075 Å
Hall symbol: -P 2a 2bcCell parameters from 14701 reflections
a = 18.5082 (17) Åθ = 3.7–26.1º
b = 26.199 (3) ŵ = 0.55 mm−1
c = 7.1726 (6) ÅT = 93 K
V = 3478.0 (6) Å3Block, black
Z = 40.26 × 0.10 × 0.09 mm
Data collection top
Rigaku R-AXIS RAPID
diffractometer		1916 reflections with I > 2σ(I)
Detector resolution: 10.00 pixels mm-1Rint = 0.153
ω scansθmax = 26.0º
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)		h = −22→22
Tmin = 0.890, Tmax = 0.947k = −32→31
22709 measured reflectionsl = −8→8
3314 independent reflections
Refinement top
Refinement on F2H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.110  w = 1/[σ2(Fo2) + (0.2P)2
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.318(Δ/σ)max < 0.001
S = 1.04Δρmax = 2.03 e Å−3
3314 reflectionsΔρmin = −0.59 e Å−3
238 parametersExtinction correction: none
Crystal data top
[CrNa(C16H9ClN2O2)2(C3H6O)2]V = 3478.0 (6) Å3
Mr = 784.55Z = 4
Orthorhombic, PnnaMo Kα
a = 18.5082 (17) ŵ = 0.55 mm−1
b = 26.199 (3) ÅT = 93 K
c = 7.1726 (6) Å0.26 × 0.10 × 0.09 mm
Data collection top
Rigaku R-AXIS RAPID
diffractometer		3314 independent reflections
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)		1916 reflections with I > 2σ(I)
Tmin = 0.890, Tmax = 0.947Rint = 0.153
22709 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.110238 parameters
wR(F2) = 0.318H-atom parameters constrained
S = 1.04Δρmax = 2.03 e Å−3
3314 reflectionsΔρmin = −0.59 e Å−3
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
Cr10.80893 (8)0.25000.25000.0380 (5)
Cl10.63892 (10)0.02267 (8)0.4102 (2)0.0539 (6)
Na10.7960 (2)0.2500−0.25000.0467 (9)
O10.8822 (2)0.24781 (18)0.0550 (6)0.0435 (11)
O20.7318 (2)0.2380 (2)0.4390 (6)0.0513 (12)
O30.8062 (2)0.1638 (2)−0.2260 (6)0.0512 (12)
N10.8117 (2)0.1729 (2)0.2488 (6)0.0351 (11)
N20.8617 (2)0.1418 (2)0.2019 (6)0.0407 (13)
C10.6658 (3)0.0867 (2)0.4209 (8)0.0462 (16)
C20.6242 (3)0.1212 (3)0.5099 (8)0.0461 (17)
C30.6441 (3)0.1722 (2)0.5183 (9)0.0437 (15)
C40.7078 (3)0.1896 (2)0.4309 (8)0.0407 (15)
C50.7492 (3)0.1516 (2)0.3324 (9)0.0426 (15)
C60.7292 (3)0.1006 (2)0.3330 (9)0.0435 (15)
C70.9324 (3)0.2119 (2)0.0575 (7)0.0396 (15)
C81.0020 (3)0.2267 (3)−0.0206 (8)0.0451 (15)
C91.0569 (3)0.1937 (2)−0.0250 (8)0.0461 (16)
C101.0507 (3)0.1422 (2)0.0373 (7)0.0434 (16)
C111.1093 (3)0.1072 (3)0.0275 (8)0.0458 (16)
C121.1004 (3)0.0574 (2)0.0811 (8)0.0462 (16)
C131.0341 (3)0.0416 (2)0.1532 (8)0.0457 (15)
C140.9764 (3)0.0742 (2)0.1681 (8)0.0445 (16)
C150.9825 (3)0.1249 (2)0.1113 (7)0.0371 (14)
C160.9246 (3)0.1624 (2)0.1233 (7)0.0385 (14)
C170.8410 (4)0.1242 (3)−0.2542 (7)0.0484 (17)
C180.8125 (4)0.0736 (3)−0.1908 (11)0.0583 (19)
C190.9106 (3)0.1238 (3)−0.3583 (10)0.0561 (19)
H20.58150.11070.56650.055*
H30.61510.19530.58240.052*
H60.75800.07610.27530.052*
H81.00820.2595−0.06780.054*
H91.10130.2048−0.07060.055*
H111.15400.1182−0.01560.055*
H121.13830.03430.06950.055*
H131.02890.00800.19240.055*
H140.93290.06240.21650.053*
H18A0.85130.0536−0.14060.087*
H18B0.79130.0560−0.29480.087*
H18C0.77640.0789−0.09650.087*
H19A0.94900.1139−0.27590.084*
H19B0.92020.1573−0.40660.084*
H19C0.90760.0999−0.45950.084*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cr10.0287 (8)0.0449 (9)0.0405 (8)0.00000.00000.0033 (5)
Cl10.0448 (10)0.0658 (13)0.0511 (10)−0.0180 (8)0.0053 (7)−0.0007 (7)
Na10.046 (2)0.048 (2)0.046 (2)0.00000.00000.0035 (15)
O10.032 (2)0.058 (3)0.040 (2)−0.001 (2)−0.0023 (18)0.0069 (19)
O20.024 (2)0.077 (3)0.053 (2)0.007 (2)−0.001 (2)0.005 (2)
O30.045 (3)0.056 (3)0.052 (2)0.006 (2)−0.019 (2)−0.002 (2)
N10.027 (2)0.043 (3)0.035 (2)0.001 (2)0.001 (2)−0.001 (2)
N20.023 (2)0.065 (4)0.033 (2)0.002 (2)0.0005 (19)0.007 (2)
C10.034 (3)0.063 (4)0.042 (3)−0.009 (3)−0.008 (2)−0.001 (3)
C20.021 (3)0.076 (5)0.041 (3)−0.017 (3)−0.002 (2)0.002 (3)
C30.021 (3)0.059 (4)0.051 (3)0.005 (2)0.001 (2)0.012 (3)
C40.020 (2)0.057 (4)0.044 (3)−0.004 (2)−0.001 (2)0.007 (2)
C50.023 (3)0.055 (4)0.050 (3)−0.005 (2)−0.008 (2)0.006 (3)
C60.025 (3)0.058 (4)0.048 (3)−0.001 (2)0.002 (2)0.005 (3)
C70.018 (2)0.070 (4)0.031 (2)−0.002 (2)−0.001 (2)−0.003 (2)
C80.023 (3)0.076 (4)0.037 (3)−0.002 (3)−0.003 (2)0.003 (3)
C90.027 (3)0.071 (4)0.040 (3)0.003 (3)−0.003 (2)0.005 (3)
C100.018 (2)0.080 (5)0.032 (2)−0.001 (2)0.001 (2)−0.002 (3)
C110.033 (3)0.070 (5)0.034 (3)0.002 (3)0.002 (2)−0.004 (3)
C120.039 (3)0.062 (4)0.037 (3)0.010 (3)0.007 (2)−0.003 (3)
C130.045 (4)0.049 (4)0.043 (3)0.006 (3)−0.008 (3)−0.001 (3)
C140.032 (3)0.060 (4)0.041 (3)0.006 (3)−0.001 (2)−0.003 (3)
C150.026 (3)0.054 (4)0.031 (2)−0.005 (2)0.002 (2)−0.004 (2)
C160.022 (3)0.057 (4)0.037 (2)−0.003 (2)−0.004 (2)0.008 (2)
C170.048 (4)0.062 (5)0.035 (3)−0.002 (3)−0.009 (2)−0.007 (3)
C180.039 (4)0.066 (5)0.070 (4)−0.007 (3)0.010 (3)0.007 (4)
C190.040 (4)0.078 (5)0.050 (3)−0.013 (3)0.000 (3)−0.005 (3)
Geometric parameters (Å, °) top
Cr1—O11.948 (4)C6—H60.930
Cr1—O1i1.948 (4)C7—C81.458 (8)
Cr1—O21.993 (4)C7—C161.386 (9)
Cr1—O2i1.993 (4)C8—C91.336 (10)
Cr1—N12.021 (5)C8—H80.930
Cr1—N1i2.021 (5)C9—C101.426 (10)
Cl1—C11.752 (7)C9—H90.930
Na1—O12.708 (4)C10—C111.421 (9)
Na1—O1ii2.708 (4)C10—C151.443 (8)
Na1—O2iii2.547 (4)C11—C121.371 (10)
Na1—O2i2.547 (4)C11—H110.930
Na1—O32.274 (5)C12—C131.394 (9)
Na1—O3ii2.274 (5)C12—H120.930
O1—C71.323 (7)C13—C141.372 (9)
O2—C41.345 (8)C13—H130.930
O3—C171.238 (9)C14—C151.393 (9)
N1—N21.278 (7)C14—H140.930
N1—C51.418 (7)C15—C161.456 (8)
N2—C161.403 (7)C17—C181.497 (11)
C1—C21.349 (9)C17—C191.488 (10)
C1—C61.381 (9)C18—H18A0.960
C2—C31.386 (10)C18—H18B0.960
C2—H20.930C18—H18C0.960
C3—C41.411 (8)C19—H19A0.960
C3—H30.930C19—H19B0.960
C4—C51.440 (9)C19—H19C0.960
C5—C61.387 (9)
O1—Cr1—O1i91.84 (19)C3—C4—C5116.0 (6)
O1—Cr1—O2169.0 (2)N1—C5—C4111.7 (5)
O1—Cr1—O2i90.83 (18)N1—C5—C6126.7 (5)
O1—Cr1—N187.12 (19)C4—C5—C6121.6 (5)
O1—Cr1—N1i90.86 (19)C1—C6—C5118.7 (6)
O1i—Cr1—O290.83 (18)C1—C6—H6120.6
O1i—Cr1—O2i169.0 (2)C5—C6—H6120.6
O1i—Cr1—N190.86 (19)O1—C7—C8115.1 (6)
O1i—Cr1—N1i87.12 (19)O1—C7—C16126.7 (5)
O2—Cr1—O2i88.56 (19)C8—C7—C16118.2 (5)
O2—Cr1—N182.2 (2)C7—C8—C9120.6 (7)
O2—Cr1—N1i100.0 (2)C7—C8—H8119.7
O2i—Cr1—N1100.0 (2)C9—C8—H8119.7
O2i—Cr1—N1i82.2 (2)C8—C9—C10122.9 (6)
N1—Cr1—N1i177.1 (2)C8—C9—H9118.5
O1—Na1—O1ii107.84 (18)C10—C9—H9118.5
O1—Na1—O2iii168.44 (17)C9—C10—C11122.2 (5)
O1—Na1—O2i64.50 (13)C9—C10—C15118.9 (5)
O1—Na1—O382.45 (16)C11—C10—C15118.9 (6)
O1—Na1—O3ii91.90 (16)C10—C11—C12120.6 (6)
O1ii—Na1—O2iii64.50 (13)C10—C11—H11119.7
O1ii—Na1—O2i168.44 (17)C12—C11—H11119.7
O1ii—Na1—O391.90 (16)C11—C12—C13119.5 (6)
O1ii—Na1—O3ii82.45 (16)C11—C12—H12120.3
O2iii—Na1—O2i124.4 (2)C13—C12—H12120.3
O2iii—Na1—O389.00 (17)C12—C13—C14121.9 (6)
O2iii—Na1—O3ii95.46 (17)C12—C13—H13119.0
O2i—Na1—O395.46 (17)C14—C13—H13119.0
O2i—Na1—O3ii89.00 (17)C13—C14—C15120.5 (6)
O3—Na1—O3ii170.4 (2)C13—C14—H14119.7
Cr1—O1—Na199.77 (18)C15—C14—H14119.7
Cr1—O1—C7120.0 (3)C10—C15—C14118.5 (5)
Na1—O1—C7116.1 (3)C10—C15—C16116.9 (6)
Cr1—O2—Na1iv104.03 (19)C14—C15—C16124.5 (5)
Cr1—O2—C4110.9 (3)N2—C16—C7125.6 (5)
Na1iv—O2—C4107.9 (3)N2—C16—C15112.0 (5)
Na1—O3—C17149.7 (4)C7—C16—C15122.4 (5)
Cr1—N1—N2131.1 (4)O3—C17—C18120.5 (6)
Cr1—N1—C5111.7 (4)O3—C17—C19122.6 (7)
N2—N1—C5116.8 (5)C18—C17—C19116.9 (6)
N1—N2—C16117.4 (5)C17—C18—H18A109.5
Cl1—C1—C2120.0 (5)C17—C18—H18B109.5
Cl1—C1—C6118.3 (5)C17—C18—H18C109.5
C2—C1—C6121.7 (6)H18A—C18—H18B109.5
C1—C2—C3120.9 (6)H18A—C18—H18C109.5
C1—C2—H2119.5H18B—C18—H18C109.5
C3—C2—H2119.5C17—C19—H19A109.5
C2—C3—C4120.9 (6)C17—C19—H19B109.5
C2—C3—H3119.5C17—C19—H19C109.5
C4—C3—H3119.5H19A—C19—H19B109.5
O2—C4—C3124.2 (6)H19A—C19—H19C109.5
O2—C4—C5119.8 (5)H19B—C19—H19C109.5
O1—Cr1—O1i—C7i55.3 (4)O3—Na1—O1ii—C7ii−135.0 (4)
O1i—Cr1—O1—Na1−176.84 (18)O1ii—Na1—O3ii—C17ii−80.9 (8)
O1i—Cr1—O1—C755.3 (4)O3ii—Na1—O1ii—C7ii37.2 (4)
O1—Cr1—O2—C4−3.6 (12)O2iii—Na1—O2i—Cr1165.00 (18)
O1—Cr1—O2—Na1iv112.2 (9)O2iii—Na1—O2i—C4i−77.2 (4)
O2—Cr1—O1—Na179.2 (10)O2i—Na1—O2iii—Cr1iii165.00 (18)
O2—Cr1—O1—C7−48.7 (12)O2i—Na1—O2iii—C4iii−77.2 (4)
O1—Cr1—O2i—C4i−107.6 (4)O2iii—Na1—O3—C1791.2 (8)
O1—Cr1—O2i—Na18.1 (2)O3—Na1—O2iii—Cr1iii−99.1 (2)
O2i—Cr1—O1—Na1−7.5 (2)O3—Na1—O2iii—C4iii18.7 (3)
O2i—Cr1—O1—C7−135.4 (4)O2iii—Na1—O3ii—C17ii−144.3 (8)
O1—Cr1—N1—N225.7 (4)O3ii—Na1—O2iii—Cr1iii72.5 (2)
O1—Cr1—N1—C5−161.3 (3)O3ii—Na1—O2iii—C4iii−169.7 (3)
N1—Cr1—O1—Na192.39 (18)O2i—Na1—O3—C17−144.3 (8)
N1—Cr1—O1—C7−35.5 (4)O3—Na1—O2i—Cr172.5 (2)
O1—Cr1—N1i—N2i−66.1 (4)O3—Na1—O2i—C4i−169.7 (3)
O1—Cr1—N1i—C5i106.9 (3)O2i—Na1—O3ii—C17ii91.2 (8)
N1i—Cr1—O1—Na1−89.70 (18)O3ii—Na1—O2i—Cr1−99.1 (2)
N1i—Cr1—O1—C7142.4 (4)O3ii—Na1—O2i—C4i18.7 (3)
O1i—Cr1—O2—C4−107.6 (4)Cr1—O1—C7—C8−148.7 (4)
O1i—Cr1—O2—Na1iv8.1 (2)Cr1—O1—C7—C1632.3 (7)
O2—Cr1—O1i—C7i−135.4 (4)Na1—O1—C7—C891.2 (5)
O1i—Cr1—O2i—C4i−3.6 (12)Na1—O1—C7—C16−87.7 (6)
O1i—Cr1—O2i—Na1112.2 (9)Cr1—O2—C4—C3−166.3 (5)
O2i—Cr1—O1i—C7i−48.7 (12)Cr1—O2—C4—C515.4 (6)
O1i—Cr1—N1—N2−66.1 (4)Na1iv—O2—C4—C380.3 (6)
O1i—Cr1—N1—C5106.9 (3)Na1iv—O2—C4—C5−98.0 (5)
N1—Cr1—O1i—C7i142.4 (4)Na1—O3—C17—C18178.8 (6)
O1i—Cr1—N1i—N2i25.7 (4)Na1—O3—C17—C19−3.9 (12)
O1i—Cr1—N1i—C5i−161.3 (3)Cr1—N1—N2—C16−5.7 (7)
N1i—Cr1—O1i—C7i−35.5 (4)Cr1—N1—C5—C4−12.3 (6)
O2—Cr1—O2i—C4i83.4 (4)Cr1—N1—C5—C6170.9 (5)
O2—Cr1—O2i—Na1−160.9 (2)N2—N1—C5—C4161.7 (5)
O2i—Cr1—O2—C483.4 (4)N2—N1—C5—C6−15.0 (8)
O2i—Cr1—O2—Na1iv−160.9 (2)C5—N1—N2—C16−178.4 (4)
O2—Cr1—N1—N2−156.8 (4)N1—N2—C16—C7−13.7 (8)
O2—Cr1—N1—C516.2 (3)N1—N2—C16—C15168.4 (4)
N1—Cr1—O2—C4−16.9 (3)Cl1—C1—C2—C3−179.3 (4)
N1—Cr1—O2—Na1iv98.9 (2)Cl1—C1—C6—C5176.7 (4)
O2—Cr1—N1i—N2i116.1 (4)C2—C1—C6—C5−1.8 (9)
O2—Cr1—N1i—C5i−71.0 (3)C6—C1—C2—C3−0.8 (9)
N1i—Cr1—O2—C4165.2 (3)C1—C2—C3—C41.2 (9)
N1i—Cr1—O2—Na1iv−79.1 (2)C2—C3—C4—O2−177.5 (5)
O2i—Cr1—N1—N2116.1 (4)C2—C3—C4—C50.9 (9)
O2i—Cr1—N1—C5−71.0 (3)O2—C4—C5—N1−2.0 (8)
N1—Cr1—O2i—C4i165.2 (3)O2—C4—C5—C6175.0 (5)
N1—Cr1—O2i—Na1−79.1 (2)C3—C4—C5—N1179.6 (5)
O2i—Cr1—N1i—N2i−156.8 (4)C3—C4—C5—C6−3.5 (9)
O2i—Cr1—N1i—C5i16.2 (3)N1—C5—C6—C1−179.6 (5)
N1i—Cr1—O2i—C4i−16.9 (3)C4—C5—C6—C14.0 (9)
N1i—Cr1—O2i—Na198.9 (2)O1—C7—C8—C9179.7 (5)
O1—Na1—O1ii—C7ii−52.4 (4)O1—C7—C16—N2−0.9 (9)
O1ii—Na1—O1—Cr1177.19 (16)O1—C7—C16—C15176.9 (5)
O1ii—Na1—O1—C7−52.4 (4)C8—C7—C16—N2−179.8 (5)
O1—Na1—O2iii—Cr1iii−56.8 (9)C8—C7—C16—C15−2.1 (8)
O1—Na1—O2iii—C4iii61.0 (10)C16—C7—C8—C9−1.2 (8)
O2iii—Na1—O1—Cr1−135.9 (8)C7—C8—C9—C102.8 (9)
O2iii—Na1—O1—C7−5.5 (10)C8—C9—C10—C11178.5 (6)
O1—Na1—O2i—Cr1−6.48 (17)C8—C9—C10—C15−1.0 (9)
O1—Na1—O2i—C4i111.3 (3)C9—C10—C11—C12−177.2 (5)
O2i—Na1—O1—Cr16.53 (17)C9—C10—C15—C14178.7 (5)
O2i—Na1—O1—C7137.0 (4)C9—C10—C15—C16−2.1 (8)
O1—Na1—O3—C17−80.9 (8)C11—C10—C15—C14−0.8 (8)
O3—Na1—O1—Cr1−93.2 (2)C11—C10—C15—C16178.4 (5)
O3—Na1—O1—C737.2 (4)C15—C10—C11—C122.3 (8)
O1—Na1—O3ii—C17ii26.8 (8)C10—C11—C12—C13−2.8 (9)
O3ii—Na1—O1—Cr194.5 (2)C11—C12—C13—C141.7 (9)
O3ii—Na1—O1—C7−135.0 (4)C12—C13—C14—C15−0.2 (7)
O1ii—Na1—O2iii—Cr1iii−6.48 (17)C13—C14—C15—C10−0.2 (7)
O1ii—Na1—O2iii—C4iii111.3 (3)C13—C14—C15—C16−179.3 (5)
O2iii—Na1—O1ii—C7ii137.0 (4)C10—C15—C16—N2−178.3 (4)
O1ii—Na1—O2i—Cr1−56.8 (9)C10—C15—C16—C73.7 (8)
O1ii—Na1—O2i—C4i61.0 (9)C14—C15—C16—N20.8 (8)
O2i—Na1—O1ii—C7ii−5.5 (10)C14—C15—C16—C7−177.2 (5)
O1ii—Na1—O3—C1726.8 (8)
Symmetry codes: (i) x, −y+1/2, −z+1/2; (ii) x, −y+1/2, −z−1/2; (iii) x, y, z−1; (iv) x, y, z+1.
Table 1
Selected geometric parameters (Å, °) top
Cr1—O11.948 (4)Na1—O12.708 (4)
Cr1—O1i1.948 (4)Na1—O1ii2.708 (4)
Cr1—O21.993 (4)Na1—O2iii2.547 (4)
Cr1—O2i1.993 (4)Na1—O2i2.547 (4)
Cr1—N12.021 (5)Na1—O32.274 (5)
Cr1—N1i2.021 (5)Na1—O3ii2.274 (5)
Cl1—C11.752 (7)
O1—Cr1—O1i91.84 (19)O1—Na1—O2iii168.44 (17)
O1—Cr1—O2169.0 (2)O1—Na1—O2i64.50 (13)
O1—Cr1—O2i90.83 (18)O1—Na1—O382.45 (16)
O1—Cr1—N187.12 (19)O1—Na1—O3ii91.90 (16)
O1—Cr1—N1i90.86 (19)O1ii—Na1—O2iii64.50 (13)
O1i—Cr1—O290.83 (18)O1ii—Na1—O2i168.44 (17)
O1i—Cr1—O2i169.0 (2)O1ii—Na1—O391.90 (16)
O1i—Cr1—N190.86 (19)O1ii—Na1—O3ii82.45 (16)
O1i—Cr1—N1i87.12 (19)O2iii—Na1—O2i124.4 (2)
O2—Cr1—O2i88.56 (19)O2iii—Na1—O389.00 (17)
O2—Cr1—N182.2 (2)O2iii—Na1—O3ii95.46 (17)
O2—Cr1—N1i100.0 (2)O2i—Na1—O395.46 (17)
O2i—Cr1—N1100.0 (2)O2i—Na1—O3ii89.00 (17)
O2i—Cr1—N1i82.2 (2)O3—Na1—O3ii170.4 (2)
N1—Cr1—N1i177.1 (2)Cr1—O1—Na199.77 (18)
O1—Na1—O1ii107.84 (18)Cr1—O2—Na1iv104.03 (19)
Symmetry codes: (i) x, −y+1/2, −z+1/2; (ii) x, −y+1/2, −z−1/2; (iii) x, y, z−1; (iv) x, y, z+1.
references
References top

Burla, M. C., Caliandro, R., Camalli, M., Carrozzini, B., Cascarano, G. L., De Caro, L., Giacovazzo, C., Polidori, G. & Spagna, R. (2005). J. Appl. Cryst. 38, 381–388.

Burnett, M. N. & Johnson, C. K. (1996). ORTEPIII. Report ORNL-6895. Oak Ridge National Laboratory. Tennessee, USA.

Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.

Mizuguchi, J., Sato, Y. & Uta, K. (2007a). Acta Cryst. E63, m1327–m1328.

Mizuguchi, J., Sato, Y. & Uta, K. (2007b). Acta Cryst. E63, m1377–m1378.

Mizuguchi, J., Sato, Y., Uta, K. & Sato, K. (2007). Acta Cryst. E63, o2509–o2510.

Mizuguchi, J., Uta, K. & Sato, Y. (2007). Acta Cryst. E63, m1329–m1330.

Rigaku (1998). PROCESS-AUTO. Rigaku Corporation, Tokyo, Japan.

Rigaku/MSC (2006). CrystalStructure. Version 3.8. Rigaku/MSC, The Woodlands, Texas, USA.

Sato, Y., Uta, K. & Mizuguchi, J. (2008). Acta Cryst. E64, m240–m241.

Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.

Tanaka, K. (1995). J. Electrostatics (Jpn Version), 19, 15-21.

Yasumatsu, M., Kuroda, K., Yamate, O., Sato, K., Hikata, J. & Yushina, H. (2006). JP Patent 2006–113 576A.