metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 64| Part 2| February 2008| Pages m333-m334

Poly[bis­­(acetone-κO)bis­­{μ3-1-[(5-chloro-2-oxido­phenyl)diazenyl]-2-naphtholato-κ4O:O,O′:O′}­sodium(I)­chromium(III)]

aDepartment of Applied Physics, Faculty of Engineering, Yokohama National University, Tokiwadai 79-5, Hodogaya-ku, Yokohama 240-8501, Japan, and bDepartment of Applied Physics, Graduate School of Engineering, Yokohama National University, Tokiwadai 79-5, Hodogaya-ku, Yokohama 240-8501, Japan
*Correspondence e-mail: mizu-j@ynu.ac.jp

(Received 16 December 2007; accepted 7 January 2008; online 11 January 2008)

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.

Related literature

For general background to charge-control agents, see: Tanaka (1995[Tanaka, K. (1995). J. Electrostatics (Jpn. Version), 19, 15-21.]). For the preparation of the title compound, see: Yasumatsu et al. (2006[Yasumatsu, M., Kuroda, K., Yamate, O., Sato, K., Hikata, J. & Yushina, H. (2006). JP Patent 2006-113576A.]). For related structures, see: Mizuguchi, Sato, Uta & Sato (2007[Mizuguchi, J., Sato, Y., Uta, K. & Sato, K. (2007). Acta Cryst. E63, o2509-o2510.]); Mizuguchi et al. (2007a[Mizuguchi, J., Sato, Y. & Uta, K. (2007a). Acta Cryst. E63, m1327-m1328.],b[Mizuguchi, J., Sato, Y. & Uta, K. (2007b). Acta Cryst. E63, m1377-m1378.]); Mizuguchi, Uta & Sato (2007[Mizuguchi, J., Uta, K. & Sato, Y. (2007). Acta Cryst. E63, m1329-m1330.]); Sato et al. (2008[Sato, Y., Uta, K. & Mizuguchi, J. (2008). Acta Cryst. E64, m240-m241.]).

[Scheme 1]

Experimental

Crystal data
  • [CrNa(C16H9ClN2O2)2(C3H6O)2]

  • Mr = 784.55

  • Orthorhombic, P n n a

  • a = 18.5082 (17) Å

  • b = 26.199 (3) Å

  • c = 7.1726 (6) Å

  • V = 3478.0 (6) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.55 mm−1

  • T = 93 K

  • 0.26 × 0.10 × 0.09 mm

Data collection
  • Rigaku R-AXIS RAPID diffractometer

  • Absorption correction: multi-scan (ABSCOR; Higashi, 1995[Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.890, Tmax = 0.947

  • 22709 measured reflections

  • 3314 independent reflections

  • 1916 reflections with I > 2σ(I)

  • Rint = 0.153

Refinement
  • R[F2 > 2σ(F2)] = 0.110

  • wR(F2) = 0.318

  • S = 1.03

  • 3314 reflections

  • 238 parameters

  • H-atom parameters constrained

  • Δρmax = 2.03 e Å−3

  • Δρmin = −0.59 e Å−3

Table 1
Selected geometric parameters (Å, °)

Cr1—O1 1.948 (4)
Cr1—O1i 1.948 (4)
Cr1—O2 1.993 (4)
Cr1—O2i 1.993 (4)
Cr1—N1 2.021 (5)
Cr1—N1i 2.021 (5)
Cl1—C1 1.752 (7)
Na1—O1 2.708 (4)
Na1—O1ii 2.708 (4)
Na1—O2iii 2.547 (4)
Na1—O2i 2.547 (4)
Na1—O3 2.274 (5)
Na1—O3ii 2.274 (5)
O1—Cr1—O1i 91.84 (19)
O1—Cr1—O2 169.0 (2)
O1—Cr1—O2i 90.83 (18)
O1—Cr1—N1 87.12 (19)
O1—Cr1—N1i 90.86 (19)
O2—Cr1—O2i 88.56 (19)
O2—Cr1—N1 82.2 (2)
O2—Cr1—N1i 100.0 (2)
N1—Cr1—N1i 177.1 (2)
O1—Na1—O1ii 107.84 (18)
O1—Na1—O2iii 168.44 (17)
O1—Na1—O2i 64.50 (13)
O1—Na1—O3 82.45 (16)
O1—Na1—O3ii 91.90 (16)
O2iii—Na1—O2i 124.4 (2)
O2iii—Na1—O3 89.00 (17)
O2iii—Na1—O3ii 95.46 (17)
O3—Na1—O3ii 170.4 (2)
Cr1—O1—Na1 99.77 (18)
Cr1—O2—Na1iv 104.03 (19)
Symmetry codes: (i) [x, -y+{\script{1\over 2}}, -z+{\script{1\over 2}}]; (ii) [x, -y+{\script{1\over 2}}, -z-{\script{1\over 2}}]; (iii) x, y, z-1; (iv) x, y, z+1.

Data collection: PROCESS-AUTO (Rigaku, 1998[Rigaku (1998). PROCESS-AUTO. Rigaku Corporation, Tokyo, Japan.]); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2006[Rigaku/MSC (2006). CrystalStructure. Version 3.8. Rigaku/MSC, The Woodlands, Texas, USA.]); program(s) used to solve structure: SIR2004 (Burla et al., 2005[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.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEPIII (Burnett & Johnson, 1996[Burnett, M. N. & Johnson, C. K. (1996). ORTEPIII. Report ORNL-6895. Oak Ridge National Laboratory, Tennessee, USA.]); software used to prepare material for publication: CrystalStructure.

Supporting information


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]F(000) = 1612.00
Mr = 784.55Dx = 1.498 Mg m3
Orthorhombic, PnnaMo Kα radiation, λ = 0.71075 Å
Hall symbol: -P 2a 2bcCell parameters from 14701 reflections
a = 18.5082 (17) Åθ = 3.7–26.1°
b = 26.199 (3) ŵ = 0.55 mm1
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 = 26.0°
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)
h = 2222
Tmin = 0.890, Tmax = 0.947k = 3231
22709 measured reflectionsl = 88
3314 independent reflections
Refinement top
Refinement on F20 restraints
R[F2 > 2σ(F2)] = 0.110H-atom parameters constrained
wR(F2) = 0.318 w = 1/[σ2(Fo2) + (0.2P)2
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max < 0.001
3314 reflectionsΔρmax = 2.03 e Å3
238 parametersΔρmin = 0.59 e Å3
Crystal data top
[CrNa(C16H9ClN2O2)2(C3H6O)2]V = 3478.0 (6) Å3
Mr = 784.55Z = 4
Orthorhombic, PnnaMo Kα radiation
a = 18.5082 (17) ŵ = 0.55 mm1
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)] = 0.1100 restraints
wR(F2) = 0.318H-atom parameters constrained
S = 1.04Δρmax = 2.03 e Å3
3314 reflectionsΔρmin = 0.59 e Å3
238 parameters
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
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)0.25000.25000.0467 (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*
H81.00820.25950.06780.054*
H91.10130.20480.07060.055*
H111.15400.11820.01560.055*
H121.13830.03430.06950.055*
H131.02890.00800.19240.055*
H140.93290.06240.21650.053*
H18A0.85130.05360.14060.087*
H18B0.79130.05600.29480.087*
H18C0.77640.07890.09650.087*
H19A0.94900.11390.27590.084*
H19B0.92020.15730.40660.084*
H19C0.90760.09990.45950.084*
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, º) 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—C7ii135.0 (4)
O1i—Cr1—O1—Na1176.84 (18)O1ii—Na1—O3ii—C17ii80.9 (8)
O1i—Cr1—O1—C755.3 (4)O3ii—Na1—O1ii—C7ii37.2 (4)
O1—Cr1—O2—C43.6 (12)O2iii—Na1—O2i—Cr1165.00 (18)
O1—Cr1—O2—Na1iv112.2 (9)O2iii—Na1—O2i—C4i77.2 (4)
O2—Cr1—O1—Na179.2 (10)O2i—Na1—O2iii—Cr1iii165.00 (18)
O2—Cr1—O1—C748.7 (12)O2i—Na1—O2iii—C4iii77.2 (4)
O1—Cr1—O2i—C4i107.6 (4)O2iii—Na1—O3—C1791.2 (8)
O1—Cr1—O2i—Na18.1 (2)O3—Na1—O2iii—Cr1iii99.1 (2)
O2i—Cr1—O1—Na17.5 (2)O3—Na1—O2iii—C4iii18.7 (3)
O2i—Cr1—O1—C7135.4 (4)O2iii—Na1—O3ii—C17ii144.3 (8)
O1—Cr1—N1—N225.7 (4)O3ii—Na1—O2iii—Cr1iii72.5 (2)
O1—Cr1—N1—C5161.3 (3)O3ii—Na1—O2iii—C4iii169.7 (3)
N1—Cr1—O1—Na192.39 (18)O2i—Na1—O3—C17144.3 (8)
N1—Cr1—O1—C735.5 (4)O3—Na1—O2i—Cr172.5 (2)
O1—Cr1—N1i—N2i66.1 (4)O3—Na1—O2i—C4i169.7 (3)
O1—Cr1—N1i—C5i106.9 (3)O2i—Na1—O3ii—C17ii91.2 (8)
N1i—Cr1—O1—Na189.70 (18)O3ii—Na1—O2i—Cr199.1 (2)
N1i—Cr1—O1—C7142.4 (4)O3ii—Na1—O2i—C4i18.7 (3)
O1i—Cr1—O2—C4107.6 (4)Cr1—O1—C7—C8148.7 (4)
O1i—Cr1—O2—Na1iv8.1 (2)Cr1—O1—C7—C1632.3 (7)
O2—Cr1—O1i—C7i135.4 (4)Na1—O1—C7—C891.2 (5)
O1i—Cr1—O2i—C4i3.6 (12)Na1—O1—C7—C1687.7 (6)
O1i—Cr1—O2i—Na1112.2 (9)Cr1—O2—C4—C3166.3 (5)
O2i—Cr1—O1i—C7i48.7 (12)Cr1—O2—C4—C515.4 (6)
O1i—Cr1—N1—N266.1 (4)Na1iv—O2—C4—C380.3 (6)
O1i—Cr1—N1—C5106.9 (3)Na1iv—O2—C4—C598.0 (5)
N1—Cr1—O1i—C7i142.4 (4)Na1—O3—C17—C18178.8 (6)
O1i—Cr1—N1i—N2i25.7 (4)Na1—O3—C17—C193.9 (12)
O1i—Cr1—N1i—C5i161.3 (3)Cr1—N1—N2—C165.7 (7)
N1i—Cr1—O1i—C7i35.5 (4)Cr1—N1—C5—C412.3 (6)
O2—Cr1—O2i—C4i83.4 (4)Cr1—N1—C5—C6170.9 (5)
O2—Cr1—O2i—Na1160.9 (2)N2—N1—C5—C4161.7 (5)
O2i—Cr1—O2—C483.4 (4)N2—N1—C5—C615.0 (8)
O2i—Cr1—O2—Na1iv160.9 (2)C5—N1—N2—C16178.4 (4)
O2—Cr1—N1—N2156.8 (4)N1—N2—C16—C713.7 (8)
O2—Cr1—N1—C516.2 (3)N1—N2—C16—C15168.4 (4)
N1—Cr1—O2—C416.9 (3)Cl1—C1—C2—C3179.3 (4)
N1—Cr1—O2—Na1iv98.9 (2)Cl1—C1—C6—C5176.7 (4)
O2—Cr1—N1i—N2i116.1 (4)C2—C1—C6—C51.8 (9)
O2—Cr1—N1i—C5i71.0 (3)C6—C1—C2—C30.8 (9)
N1i—Cr1—O2—C4165.2 (3)C1—C2—C3—C41.2 (9)
N1i—Cr1—O2—Na1iv79.1 (2)C2—C3—C4—O2177.5 (5)
O2i—Cr1—N1—N2116.1 (4)C2—C3—C4—C50.9 (9)
O2i—Cr1—N1—C571.0 (3)O2—C4—C5—N12.0 (8)
N1—Cr1—O2i—C4i165.2 (3)O2—C4—C5—C6175.0 (5)
N1—Cr1—O2i—Na179.1 (2)C3—C4—C5—N1179.6 (5)
O2i—Cr1—N1i—N2i156.8 (4)C3—C4—C5—C63.5 (9)
O2i—Cr1—N1i—C5i16.2 (3)N1—C5—C6—C1179.6 (5)
N1i—Cr1—O2i—C4i16.9 (3)C4—C5—C6—C14.0 (9)
N1i—Cr1—O2i—Na198.9 (2)O1—C7—C8—C9179.7 (5)
O1—Na1—O1ii—C7ii52.4 (4)O1—C7—C16—N20.9 (9)
O1ii—Na1—O1—Cr1177.19 (16)O1—C7—C16—C15176.9 (5)
O1ii—Na1—O1—C752.4 (4)C8—C7—C16—N2179.8 (5)
O1—Na1—O2iii—Cr1iii56.8 (9)C8—C7—C16—C152.1 (8)
O1—Na1—O2iii—C4iii61.0 (10)C16—C7—C8—C91.2 (8)
O2iii—Na1—O1—Cr1135.9 (8)C7—C8—C9—C102.8 (9)
O2iii—Na1—O1—C75.5 (10)C8—C9—C10—C11178.5 (6)
O1—Na1—O2i—Cr16.48 (17)C8—C9—C10—C151.0 (9)
O1—Na1—O2i—C4i111.3 (3)C9—C10—C11—C12177.2 (5)
O2i—Na1—O1—Cr16.53 (17)C9—C10—C15—C14178.7 (5)
O2i—Na1—O1—C7137.0 (4)C9—C10—C15—C162.1 (8)
O1—Na1—O3—C1780.9 (8)C11—C10—C15—C140.8 (8)
O3—Na1—O1—Cr193.2 (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—C132.8 (9)
O3ii—Na1—O1—Cr194.5 (2)C11—C12—C13—C141.7 (9)
O3ii—Na1—O1—C7135.0 (4)C12—C13—C14—C150.2 (7)
O1ii—Na1—O2iii—Cr1iii6.48 (17)C13—C14—C15—C100.2 (7)
O1ii—Na1—O2iii—C4iii111.3 (3)C13—C14—C15—C16179.3 (5)
O2iii—Na1—O1ii—C7ii137.0 (4)C10—C15—C16—N2178.3 (4)
O1ii—Na1—O2i—Cr156.8 (9)C10—C15—C16—C73.7 (8)
O1ii—Na1—O2i—C4i61.0 (9)C14—C15—C16—N20.8 (8)
O2i—Na1—O1ii—C7ii5.5 (10)C14—C15—C16—C7177.2 (5)
O1ii—Na1—O3—C1726.8 (8)
Symmetry codes: (i) x, y+1/2, z+1/2; (ii) x, y+1/2, z1/2; (iii) x, y, z1; (iv) x, y, z+1.

Experimental details

Crystal data
Chemical formula[CrNa(C16H9ClN2O2)2(C3H6O)2]
Mr784.55
Crystal system, space groupOrthorhombic, Pnna
Temperature (K)93
a, b, c (Å)18.5082 (17), 26.199 (3), 7.1726 (6)
V3)3478.0 (6)
Z4
Radiation typeMo Kα
µ (mm1)0.55
Crystal size (mm)0.26 × 0.10 × 0.09
Data collection
DiffractometerRigaku R-AXIS RAPID
diffractometer
Absorption correctionMulti-scan
(ABSCOR; Higashi, 1995)
Tmin, Tmax0.890, 0.947
No. of measured, independent and
observed [I > 2σ(I)] reflections
22709, 3314, 1916
Rint0.153
(sin θ/λ)max1)0.617
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.110, 0.318, 1.04
No. of reflections3314
No. of parameters238
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)2.03, 0.59

Computer programs: PROCESS-AUTO (Rigaku, 1998), CrystalStructure (Rigaku/MSC, 2006), SIR2004 (Burla et al., 2005), SHELXL97 (Sheldrick, 2008), ORTEPIII (Burnett & Johnson, 1996).

Selected geometric parameters (Å, º) 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, z1/2; (iii) x, y, z1; (iv) x, y, z+1.
 

References

First citationBurla, 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.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationBurnett, M. N. & Johnson, C. K. (1996). ORTEPIII. Report ORNL-6895. Oak Ridge National Laboratory, Tennessee, USA.  Google Scholar
First citationHigashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.  Google Scholar
First citationMizuguchi, J., Sato, Y. & Uta, K. (2007a). Acta Cryst. E63, m1327–m1328.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationMizuguchi, J., Sato, Y. & Uta, K. (2007b). Acta Cryst. E63, m1377–m1378.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationMizuguchi, J., Sato, Y., Uta, K. & Sato, K. (2007). Acta Cryst. E63, o2509–o2510.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationMizuguchi, J., Uta, K. & Sato, Y. (2007). Acta Cryst. E63, m1329–m1330.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationRigaku (1998). PROCESS-AUTO. Rigaku Corporation, Tokyo, Japan.  Google Scholar
First citationRigaku/MSC (2006). CrystalStructure. Version 3.8. Rigaku/MSC, The Woodlands, Texas, USA.  Google Scholar
First citationSato, Y., Uta, K. & Mizuguchi, J. (2008). Acta Cryst. E64, m240–m241.  Web of Science CrossRef IUCr Journals Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationTanaka, K. (1995). J. Electrostatics (Jpn. Version), 19, 15-21.  Google Scholar
First citationYasumatsu, M., Kuroda, K., Yamate, O., Sato, K., Hikata, J. & Yushina, H. (2006). JP Patent 2006-113576A.  Google Scholar

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Volume 64| Part 2| February 2008| Pages m333-m334
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