Download citation
Download citation
link to html
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.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536808000433/is2268sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536808000433/is2268Isup2.hkl
Contains datablock I

CCDC reference: 677444

Key indicators

  • Single-crystal X-ray study
  • T = 93 K
  • Mean [sigma](C-C) = 0.008 Å
  • R factor = 0.110
  • wR factor = 0.318
  • Data-to-parameter ratio = 13.9

checkCIF/PLATON results

No syntax errors found



Alert level B RINTA01_ALERT_3_B The value of Rint is greater than 0.15 Rint given 0.153 PLAT020_ALERT_3_B The value of Rint is greater than 0.10 ......... 0.15
Alert level C DIFMX01_ALERT_2_C The maximum difference density is > 0.1*ZMAX*0.75 _refine_diff_density_max given = 2.030 Test value = 1.800 DIFMX02_ALERT_1_C The maximum difference density is > 0.1*ZMAX*0.75 The relevant atom site should be identified. RFACG01_ALERT_3_C The value of the R factor is > 0.10 R factor given 0.110 RFACR01_ALERT_3_C The value of the weighted R factor is > 0.25 Weighted R factor given 0.318 PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.97 PLAT082_ALERT_2_C High R1 Value .................................. 0.11 PLAT084_ALERT_2_C High R2 Value .................................. 0.32 PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 3.44 PLAT097_ALERT_2_C Maximum (Positive) Residual Density ............ 2.03 e/A    PLAT230_ALERT_2_C Hirshfeld Test Diff for O2 - C4 .. 6.56 su PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.06 PLAT341_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 8
0 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 12 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 7 ALERT type 2 Indicator that the structure model may be wrong or deficient 6 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

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.
 

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