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

Ito, S.; Sato, Y.; Mizuguchi, J.

doi:10.1107/S1600536808000433

metal-organic compounds

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ISSN: 2056-9890

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

doi:10.1107/S1600536808000433

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

Shinpei Ito,^a Yohei Sato ^b and Jin Mizuguchi ^b ^*

^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-Cr^III complex polymer that is used as a charge-control agent in electrophotography. The monomeric unit is composed of octahedral Cr^III and Na^I units, and is characterized by twofold rotation symmetry. The Cr^III 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 Na^I atom is coordinated by two phenoxy O atoms from a neighboring Cr^III unit, two naphthoxy O atoms from another neighboring Cr^III 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 ). 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

Crystal data

[CrNa(C₁₆H₉ClN₂O₂)₂(C₃H₆O)₂]
M_r = 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 ) T_min = 0.890, T_max = 0.947
22709 measured reflections
3314 independent reflections
1916 reflections with I > 2σ(I)
R_int = 0.153

Refinement

R[F² > 2σ(F²)] = 0.110
wR(F²) = 0.318
S = 1.03
3314 reflections
238 parameters
H-atom parameters constrained
Δρ_max = 2.03 e Å⁻³
Δρ_min = −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—Na1^iv	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 ); cell refinement: PROCESS-AUTO; 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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808000433/is2268sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808000433/is2268Isup2.hkl

checkCIF report

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 Cr^III unit and an octahedral Na^I one.

Figure 1 shows the ORTEPIII plot (Burnett & Johnson, 1996) of the monomeric unit of (I). The unit is composed of an octahedral Cr^III unit and an octahedral Na^I one. The anion complex exists in cis-form, just as in the ordinary azo-Fe complexes described in the above paragraph. Each Cr^III 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 Na^I cation coordinates to a phenoxy O atom from the two ligands of each octahedral Cr^III unit, a naphthoxy O atom from the two ligands of each neighboring Cr^III unit and two acetone molecules. The octahedral Cr^III unit and the octahedral Na^I 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.

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

	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).
	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
M_r = 784.55	D_x = 1.498 Mg m⁻³
Orthorhombic, Pnna	Mo Kα radiation, λ = 0.71075 Å
Hall symbol: -P 2a 2bc	Cell parameters from 14701 reflections
a = 18.5082 (17) Å	θ = 3.7–26.1°
b = 26.199 (3) Å	µ = 0.55 mm⁻¹
c = 7.1726 (6) Å	T = 93 K
V = 3478.0 (6) Å³	Block, black
Z = 4	0.26 × 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^-1	R_int = 0.153
ω scans	θ_max = 26.0°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −22→22
T_min = 0.890, T_max = 0.947	k = −32→31
22709 measured reflections	l = −8→8
3314 independent reflections

Refinement top

Refinement on F²	0 restraints
R[F² > 2σ(F²)] = 0.110	H-atom parameters constrained
wR(F²) = 0.318	w = 1/[σ²(F_o²) + (0.2P)² where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max < 0.001
3314 reflections	Δρ_max = 2.03 e Å⁻³
238 parameters	Δρ_min = −0.59 e Å⁻³

Crystal data top

[CrNa(C₁₆H₉ClN₂O₂)₂(C₃H₆O)₂]	V = 3478.0 (6) Å³
M_r = 784.55	Z = 4
Orthorhombic, Pnna	Mo Kα radiation
a = 18.5082 (17) Å	µ = 0.55 mm⁻¹
b = 26.199 (3) Å	T = 93 K
c = 7.1726 (6) Å	0.26 × 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)
T_min = 0.890, T_max = 0.947	R_int = 0.153
22709 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.110	0 restraints
wR(F²) = 0.318	H-atom parameters constrained
S = 1.04	Δρ_max = 2.03 e Å⁻³
3314 reflections	Δρ_min = −0.59 e Å⁻³
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

	x	y	z	U_iso*/U_eq
Cr1	0.80893 (8)	0.2500	0.2500	0.0380 (5)
Cl1	0.63892 (10)	0.02267 (8)	0.4102 (2)	0.0539 (6)
Na1	0.7960 (2)	0.2500	−0.2500	0.0467 (9)
O1	0.8822 (2)	0.24781 (18)	0.0550 (6)	0.0435 (11)
O2	0.7318 (2)	0.2380 (2)	0.4390 (6)	0.0513 (12)
O3	0.8062 (2)	0.1638 (2)	−0.2260 (6)	0.0512 (12)
N1	0.8117 (2)	0.1729 (2)	0.2488 (6)	0.0351 (11)
N2	0.8617 (2)	0.1418 (2)	0.2019 (6)	0.0407 (13)
C1	0.6658 (3)	0.0867 (2)	0.4209 (8)	0.0462 (16)
C2	0.6242 (3)	0.1212 (3)	0.5099 (8)	0.0461 (17)
C3	0.6441 (3)	0.1722 (2)	0.5183 (9)	0.0437 (15)
C4	0.7078 (3)	0.1896 (2)	0.4309 (8)	0.0407 (15)
C5	0.7492 (3)	0.1516 (2)	0.3324 (9)	0.0426 (15)
C6	0.7292 (3)	0.1006 (2)	0.3330 (9)	0.0435 (15)
C7	0.9324 (3)	0.2119 (2)	0.0575 (7)	0.0396 (15)
C8	1.0020 (3)	0.2267 (3)	−0.0206 (8)	0.0451 (15)
C9	1.0569 (3)	0.1937 (2)	−0.0250 (8)	0.0461 (16)
C10	1.0507 (3)	0.1422 (2)	0.0373 (7)	0.0434 (16)
C11	1.1093 (3)	0.1072 (3)	0.0275 (8)	0.0458 (16)
C12	1.1004 (3)	0.0574 (2)	0.0811 (8)	0.0462 (16)
C13	1.0341 (3)	0.0416 (2)	0.1532 (8)	0.0457 (15)
C14	0.9764 (3)	0.0742 (2)	0.1681 (8)	0.0445 (16)
C15	0.9825 (3)	0.1249 (2)	0.1113 (7)	0.0371 (14)
C16	0.9246 (3)	0.1624 (2)	0.1233 (7)	0.0385 (14)
C17	0.8410 (4)	0.1242 (3)	−0.2542 (7)	0.0484 (17)
C18	0.8125 (4)	0.0736 (3)	−0.1908 (11)	0.0583 (19)
C19	0.9106 (3)	0.1238 (3)	−0.3583 (10)	0.0561 (19)
H2	0.5815	0.1107	0.5665	0.055*
H3	0.6151	0.1953	0.5824	0.052*
H6	0.7580	0.0761	0.2753	0.052*
H8	1.0082	0.2595	−0.0678	0.054*
H9	1.1013	0.2048	−0.0706	0.055*
H11	1.1540	0.1182	−0.0156	0.055*
H12	1.1383	0.0343	0.0695	0.055*
H13	1.0289	0.0080	0.1924	0.055*
H14	0.9329	0.0624	0.2165	0.053*
H18A	0.8513	0.0536	−0.1406	0.087*
H18B	0.7913	0.0560	−0.2948	0.087*
H18C	0.7764	0.0789	−0.0965	0.087*
H19A	0.9490	0.1139	−0.2759	0.084*
H19B	0.9202	0.1573	−0.4066	0.084*
H19C	0.9076	0.0999	−0.4595	0.084*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cr1	0.0287 (8)	0.0449 (9)	0.0405 (8)	0.0000	0.0000	0.0033 (5)
Cl1	0.0448 (10)	0.0658 (13)	0.0511 (10)	−0.0180 (8)	0.0053 (7)	−0.0007 (7)
Na1	0.046 (2)	0.048 (2)	0.046 (2)	0.0000	0.0000	0.0035 (15)
O1	0.032 (2)	0.058 (3)	0.040 (2)	−0.001 (2)	−0.0023 (18)	0.0069 (19)
O2	0.024 (2)	0.077 (3)	0.053 (2)	0.007 (2)	−0.001 (2)	0.005 (2)
O3	0.045 (3)	0.056 (3)	0.052 (2)	0.006 (2)	−0.019 (2)	−0.002 (2)
N1	0.027 (2)	0.043 (3)	0.035 (2)	0.001 (2)	0.001 (2)	−0.001 (2)
N2	0.023 (2)	0.065 (4)	0.033 (2)	0.002 (2)	0.0005 (19)	0.007 (2)
C1	0.034 (3)	0.063 (4)	0.042 (3)	−0.009 (3)	−0.008 (2)	−0.001 (3)
C2	0.021 (3)	0.076 (5)	0.041 (3)	−0.017 (3)	−0.002 (2)	0.002 (3)
C3	0.021 (3)	0.059 (4)	0.051 (3)	0.005 (2)	0.001 (2)	0.012 (3)
C4	0.020 (2)	0.057 (4)	0.044 (3)	−0.004 (2)	−0.001 (2)	0.007 (2)
C5	0.023 (3)	0.055 (4)	0.050 (3)	−0.005 (2)	−0.008 (2)	0.006 (3)
C6	0.025 (3)	0.058 (4)	0.048 (3)	−0.001 (2)	0.002 (2)	0.005 (3)
C7	0.018 (2)	0.070 (4)	0.031 (2)	−0.002 (2)	−0.001 (2)	−0.003 (2)
C8	0.023 (3)	0.076 (4)	0.037 (3)	−0.002 (3)	−0.003 (2)	0.003 (3)
C9	0.027 (3)	0.071 (4)	0.040 (3)	0.003 (3)	−0.003 (2)	0.005 (3)
C10	0.018 (2)	0.080 (5)	0.032 (2)	−0.001 (2)	0.001 (2)	−0.002 (3)
C11	0.033 (3)	0.070 (5)	0.034 (3)	0.002 (3)	0.002 (2)	−0.004 (3)
C12	0.039 (3)	0.062 (4)	0.037 (3)	0.010 (3)	0.007 (2)	−0.003 (3)
C13	0.045 (4)	0.049 (4)	0.043 (3)	0.006 (3)	−0.008 (3)	−0.001 (3)
C14	0.032 (3)	0.060 (4)	0.041 (3)	0.006 (3)	−0.001 (2)	−0.003 (3)
C15	0.026 (3)	0.054 (4)	0.031 (2)	−0.005 (2)	0.002 (2)	−0.004 (2)
C16	0.022 (3)	0.057 (4)	0.037 (2)	−0.003 (2)	−0.004 (2)	0.008 (2)
C17	0.048 (4)	0.062 (5)	0.035 (3)	−0.002 (3)	−0.009 (2)	−0.007 (3)
C18	0.039 (4)	0.066 (5)	0.070 (4)	−0.007 (3)	0.010 (3)	0.007 (4)
C19	0.040 (4)	0.078 (5)	0.050 (3)	−0.013 (3)	−0.000 (3)	−0.005 (3)

Geometric parameters (Å, º) top

Cr1—O1	1.948 (4)	C6—H6	0.930
Cr1—O1ⁱ	1.948 (4)	C7—C8	1.458 (8)
Cr1—O2	1.993 (4)	C7—C16	1.386 (9)
Cr1—O2ⁱ	1.993 (4)	C8—C9	1.336 (10)
Cr1—N1	2.021 (5)	C8—H8	0.930
Cr1—N1ⁱ	2.021 (5)	C9—C10	1.426 (10)
Cl1—C1	1.752 (7)	C9—H9	0.930
Na1—O1	2.708 (4)	C10—C11	1.421 (9)
Na1—O1ⁱⁱ	2.708 (4)	C10—C15	1.443 (8)
Na1—O2ⁱⁱⁱ	2.547 (4)	C11—C12	1.371 (10)
Na1—O2ⁱ	2.547 (4)	C11—H11	0.930
Na1—O3	2.274 (5)	C12—C13	1.394 (9)
Na1—O3ⁱⁱ	2.274 (5)	C12—H12	0.930
O1—C7	1.323 (7)	C13—C14	1.372 (9)
O2—C4	1.345 (8)	C13—H13	0.930
O3—C17	1.238 (9)	C14—C15	1.393 (9)
N1—N2	1.278 (7)	C14—H14	0.930
N1—C5	1.418 (7)	C15—C16	1.456 (8)
N2—C16	1.403 (7)	C17—C18	1.497 (11)
C1—C2	1.349 (9)	C17—C19	1.488 (10)
C1—C6	1.381 (9)	C18—H18A	0.960
C2—C3	1.386 (10)	C18—H18B	0.960
C2—H2	0.930	C18—H18C	0.960
C3—C4	1.411 (8)	C19—H19A	0.960
C3—H3	0.930	C19—H19B	0.960
C4—C5	1.440 (9)	C19—H19C	0.960
C5—C6	1.387 (9)

O1—Cr1—O1ⁱ	91.84 (19)	C3—C4—C5	116.0 (6)
O1—Cr1—O2	169.0 (2)	N1—C5—C4	111.7 (5)
O1—Cr1—O2ⁱ	90.83 (18)	N1—C5—C6	126.7 (5)
O1—Cr1—N1	87.12 (19)	C4—C5—C6	121.6 (5)
O1—Cr1—N1ⁱ	90.86 (19)	C1—C6—C5	118.7 (6)
O1ⁱ—Cr1—O2	90.83 (18)	C1—C6—H6	120.6
O1ⁱ—Cr1—O2ⁱ	169.0 (2)	C5—C6—H6	120.6
O1ⁱ—Cr1—N1	90.86 (19)	O1—C7—C8	115.1 (6)
O1ⁱ—Cr1—N1ⁱ	87.12 (19)	O1—C7—C16	126.7 (5)
O2—Cr1—O2ⁱ	88.56 (19)	C8—C7—C16	118.2 (5)
O2—Cr1—N1	82.2 (2)	C7—C8—C9	120.6 (7)
O2—Cr1—N1ⁱ	100.0 (2)	C7—C8—H8	119.7
O2ⁱ—Cr1—N1	100.0 (2)	C9—C8—H8	119.7
O2ⁱ—Cr1—N1ⁱ	82.2 (2)	C8—C9—C10	122.9 (6)
N1—Cr1—N1ⁱ	177.1 (2)	C8—C9—H9	118.5
O1—Na1—O1ⁱⁱ	107.84 (18)	C10—C9—H9	118.5
O1—Na1—O2ⁱⁱⁱ	168.44 (17)	C9—C10—C11	122.2 (5)
O1—Na1—O2ⁱ	64.50 (13)	C9—C10—C15	118.9 (5)
O1—Na1—O3	82.45 (16)	C11—C10—C15	118.9 (6)
O1—Na1—O3ⁱⁱ	91.90 (16)	C10—C11—C12	120.6 (6)
O1ⁱⁱ—Na1—O2ⁱⁱⁱ	64.50 (13)	C10—C11—H11	119.7
O1ⁱⁱ—Na1—O2ⁱ	168.44 (17)	C12—C11—H11	119.7
O1ⁱⁱ—Na1—O3	91.90 (16)	C11—C12—C13	119.5 (6)
O1ⁱⁱ—Na1—O3ⁱⁱ	82.45 (16)	C11—C12—H12	120.3
O2ⁱⁱⁱ—Na1—O2ⁱ	124.4 (2)	C13—C12—H12	120.3
O2ⁱⁱⁱ—Na1—O3	89.00 (17)	C12—C13—C14	121.9 (6)
O2ⁱⁱⁱ—Na1—O3ⁱⁱ	95.46 (17)	C12—C13—H13	119.0
O2ⁱ—Na1—O3	95.46 (17)	C14—C13—H13	119.0
O2ⁱ—Na1—O3ⁱⁱ	89.00 (17)	C13—C14—C15	120.5 (6)
O3—Na1—O3ⁱⁱ	170.4 (2)	C13—C14—H14	119.7
Cr1—O1—Na1	99.77 (18)	C15—C14—H14	119.7
Cr1—O1—C7	120.0 (3)	C10—C15—C14	118.5 (5)
Na1—O1—C7	116.1 (3)	C10—C15—C16	116.9 (6)
Cr1—O2—Na1^iv	104.03 (19)	C14—C15—C16	124.5 (5)
Cr1—O2—C4	110.9 (3)	N2—C16—C7	125.6 (5)
Na1^iv—O2—C4	107.9 (3)	N2—C16—C15	112.0 (5)
Na1—O3—C17	149.7 (4)	C7—C16—C15	122.4 (5)
Cr1—N1—N2	131.1 (4)	O3—C17—C18	120.5 (6)
Cr1—N1—C5	111.7 (4)	O3—C17—C19	122.6 (7)
N2—N1—C5	116.8 (5)	C18—C17—C19	116.9 (6)
N1—N2—C16	117.4 (5)	C17—C18—H18A	109.5
Cl1—C1—C2	120.0 (5)	C17—C18—H18B	109.5
Cl1—C1—C6	118.3 (5)	C17—C18—H18C	109.5
C2—C1—C6	121.7 (6)	H18A—C18—H18B	109.5
C1—C2—C3	120.9 (6)	H18A—C18—H18C	109.5
C1—C2—H2	119.5	H18B—C18—H18C	109.5
C3—C2—H2	119.5	C17—C19—H19A	109.5
C2—C3—C4	120.9 (6)	C17—C19—H19B	109.5
C2—C3—H3	119.5	C17—C19—H19C	109.5
C4—C3—H3	119.5	H19A—C19—H19B	109.5
O2—C4—C3	124.2 (6)	H19A—C19—H19C	109.5
O2—C4—C5	119.8 (5)	H19B—C19—H19C	109.5

O1—Cr1—O1ⁱ—C7ⁱ	55.3 (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—C7	55.3 (4)	O3ⁱⁱ—Na1—O1ⁱⁱ—C7ⁱⁱ	37.2 (4)
O1—Cr1—O2—C4	−3.6 (12)	O2ⁱⁱⁱ—Na1—O2ⁱ—Cr1	165.00 (18)
O1—Cr1—O2—Na1^iv	112.2 (9)	O2ⁱⁱⁱ—Na1—O2ⁱ—C4ⁱ	−77.2 (4)
O2—Cr1—O1—Na1	79.2 (10)	O2ⁱ—Na1—O2ⁱⁱⁱ—Cr1ⁱⁱⁱ	165.00 (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—C17	91.2 (8)
O1—Cr1—O2ⁱ—Na1	8.1 (2)	O3—Na1—O2ⁱⁱⁱ—Cr1ⁱⁱⁱ	−99.1 (2)
O2ⁱ—Cr1—O1—Na1	−7.5 (2)	O3—Na1—O2ⁱⁱⁱ—C4ⁱⁱⁱ	18.7 (3)
O2ⁱ—Cr1—O1—C7	−135.4 (4)	O2ⁱⁱⁱ—Na1—O3ⁱⁱ—C17ⁱⁱ	−144.3 (8)
O1—Cr1—N1—N2	25.7 (4)	O3ⁱⁱ—Na1—O2ⁱⁱⁱ—Cr1ⁱⁱⁱ	72.5 (2)
O1—Cr1—N1—C5	−161.3 (3)	O3ⁱⁱ—Na1—O2ⁱⁱⁱ—C4ⁱⁱⁱ	−169.7 (3)
N1—Cr1—O1—Na1	92.39 (18)	O2ⁱ—Na1—O3—C17	−144.3 (8)
N1—Cr1—O1—C7	−35.5 (4)	O3—Na1—O2ⁱ—Cr1	72.5 (2)
O1—Cr1—N1ⁱ—N2ⁱ	−66.1 (4)	O3—Na1—O2ⁱ—C4ⁱ	−169.7 (3)
O1—Cr1—N1ⁱ—C5ⁱ	106.9 (3)	O2ⁱ—Na1—O3ⁱⁱ—C17ⁱⁱ	91.2 (8)
N1ⁱ—Cr1—O1—Na1	−89.70 (18)	O3ⁱⁱ—Na1—O2ⁱ—Cr1	−99.1 (2)
N1ⁱ—Cr1—O1—C7	142.4 (4)	O3ⁱⁱ—Na1—O2ⁱ—C4ⁱ	18.7 (3)
O1ⁱ—Cr1—O2—C4	−107.6 (4)	Cr1—O1—C7—C8	−148.7 (4)
O1ⁱ—Cr1—O2—Na1^iv	8.1 (2)	Cr1—O1—C7—C16	32.3 (7)
O2—Cr1—O1ⁱ—C7ⁱ	−135.4 (4)	Na1—O1—C7—C8	91.2 (5)
O1ⁱ—Cr1—O2ⁱ—C4ⁱ	−3.6 (12)	Na1—O1—C7—C16	−87.7 (6)
O1ⁱ—Cr1—O2ⁱ—Na1	112.2 (9)	Cr1—O2—C4—C3	−166.3 (5)
O2ⁱ—Cr1—O1ⁱ—C7ⁱ	−48.7 (12)	Cr1—O2—C4—C5	15.4 (6)
O1ⁱ—Cr1—N1—N2	−66.1 (4)	Na1^iv—O2—C4—C3	80.3 (6)
O1ⁱ—Cr1—N1—C5	106.9 (3)	Na1^iv—O2—C4—C5	−98.0 (5)
N1—Cr1—O1ⁱ—C7ⁱ	142.4 (4)	Na1—O3—C17—C18	178.8 (6)
O1ⁱ—Cr1—N1ⁱ—N2ⁱ	25.7 (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—C4ⁱ	83.4 (4)	Cr1—N1—C5—C6	170.9 (5)
O2—Cr1—O2ⁱ—Na1	−160.9 (2)	N2—N1—C5—C4	161.7 (5)
O2ⁱ—Cr1—O2—C4	83.4 (4)	N2—N1—C5—C6	−15.0 (8)
O2ⁱ—Cr1—O2—Na1^iv	−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—C5	16.2 (3)	N1—N2—C16—C15	168.4 (4)
N1—Cr1—O2—C4	−16.9 (3)	Cl1—C1—C2—C3	−179.3 (4)
N1—Cr1—O2—Na1^iv	98.9 (2)	Cl1—C1—C6—C5	176.7 (4)
O2—Cr1—N1ⁱ—N2ⁱ	116.1 (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—C4	165.2 (3)	C1—C2—C3—C4	1.2 (9)
N1ⁱ—Cr1—O2—Na1^iv	−79.1 (2)	C2—C3—C4—O2	−177.5 (5)
O2ⁱ—Cr1—N1—N2	116.1 (4)	C2—C3—C4—C5	0.9 (9)
O2ⁱ—Cr1—N1—C5	−71.0 (3)	O2—C4—C5—N1	−2.0 (8)
N1—Cr1—O2ⁱ—C4ⁱ	165.2 (3)	O2—C4—C5—C6	175.0 (5)
N1—Cr1—O2ⁱ—Na1	−79.1 (2)	C3—C4—C5—N1	179.6 (5)
O2ⁱ—Cr1—N1ⁱ—N2ⁱ	−156.8 (4)	C3—C4—C5—C6	−3.5 (9)
O2ⁱ—Cr1—N1ⁱ—C5ⁱ	16.2 (3)	N1—C5—C6—C1	−179.6 (5)
N1ⁱ—Cr1—O2ⁱ—C4ⁱ	−16.9 (3)	C4—C5—C6—C1	4.0 (9)
N1ⁱ—Cr1—O2ⁱ—Na1	98.9 (2)	O1—C7—C8—C9	179.7 (5)
O1—Na1—O1ⁱⁱ—C7ⁱⁱ	−52.4 (4)	O1—C7—C16—N2	−0.9 (9)
O1ⁱⁱ—Na1—O1—Cr1	177.19 (16)	O1—C7—C16—C15	176.9 (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—C4ⁱⁱⁱ	61.0 (10)	C16—C7—C8—C9	−1.2 (8)
O2ⁱⁱⁱ—Na1—O1—Cr1	−135.9 (8)	C7—C8—C9—C10	2.8 (9)
O2ⁱⁱⁱ—Na1—O1—C7	−5.5 (10)	C8—C9—C10—C11	178.5 (6)
O1—Na1—O2ⁱ—Cr1	−6.48 (17)	C8—C9—C10—C15	−1.0 (9)
O1—Na1—O2ⁱ—C4ⁱ	111.3 (3)	C9—C10—C11—C12	−177.2 (5)
O2ⁱ—Na1—O1—Cr1	6.53 (17)	C9—C10—C15—C14	178.7 (5)
O2ⁱ—Na1—O1—C7	137.0 (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—C16	178.4 (5)
O3—Na1—O1—C7	37.2 (4)	C15—C10—C11—C12	2.3 (8)
O1—Na1—O3ⁱⁱ—C17ⁱⁱ	26.8 (8)	C10—C11—C12—C13	−2.8 (9)
O3ⁱⁱ—Na1—O1—Cr1	94.5 (2)	C11—C12—C13—C14	1.7 (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—C4ⁱⁱⁱ	111.3 (3)	C13—C14—C15—C16	−179.3 (5)
O2ⁱⁱⁱ—Na1—O1ⁱⁱ—C7ⁱⁱ	137.0 (4)	C10—C15—C16—N2	−178.3 (4)
O1ⁱⁱ—Na1—O2ⁱ—Cr1	−56.8 (9)	C10—C15—C16—C7	3.7 (8)
O1ⁱⁱ—Na1—O2ⁱ—C4ⁱ	61.0 (9)	C14—C15—C16—N2	0.8 (8)
O2ⁱ—Na1—O1ⁱⁱ—C7ⁱⁱ	−5.5 (10)	C14—C15—C16—C7	−177.2 (5)
O1ⁱⁱ—Na1—O3—C17	26.8 (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.

Experimental details

Crystal data
Chemical formula	[CrNa(C₁₆H₉ClN₂O₂)₂(C₃H₆O)₂]
M_r	784.55
Crystal system, space group	Orthorhombic, Pnna
Temperature (K)	93
a, b, c (Å)	18.5082 (17), 26.199 (3), 7.1726 (6)
V (Å³)	3478.0 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.55
Crystal size (mm)	0.26 × 0.10 × 0.09

Data collection
Diffractometer	Rigaku R-AXIS RAPID diffractometer
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995)
T_min, T_max	0.890, 0.947
No. of measured, independent and observed [I > 2σ(I)] reflections	22709, 3314, 1916
R_int	0.153
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.110, 0.318, 1.04
No. of reflections	3314
No. of parameters	238
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	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—O1	1.948 (4)	Na1—O1	2.708 (4)
Cr1—O1ⁱ	1.948 (4)	Na1—O1ⁱⁱ	2.708 (4)
Cr1—O2	1.993 (4)	Na1—O2ⁱⁱⁱ	2.547 (4)
Cr1—O2ⁱ	1.993 (4)	Na1—O2ⁱ	2.547 (4)
Cr1—N1	2.021 (5)	Na1—O3	2.274 (5)
Cr1—N1ⁱ	2.021 (5)	Na1—O3ⁱⁱ	2.274 (5)
Cl1—C1	1.752 (7)

O1—Cr1—O1ⁱ	91.84 (19)	O1—Na1—O2ⁱⁱⁱ	168.44 (17)
O1—Cr1—O2	169.0 (2)	O1—Na1—O2ⁱ	64.50 (13)
O1—Cr1—O2ⁱ	90.83 (18)	O1—Na1—O3	82.45 (16)
O1—Cr1—N1	87.12 (19)	O1—Na1—O3ⁱⁱ	91.90 (16)
O1—Cr1—N1ⁱ	90.86 (19)	O1ⁱⁱ—Na1—O2ⁱⁱⁱ	64.50 (13)
O1ⁱ—Cr1—O2	90.83 (18)	O1ⁱⁱ—Na1—O2ⁱ	168.44 (17)
O1ⁱ—Cr1—O2ⁱ	169.0 (2)	O1ⁱⁱ—Na1—O3	91.90 (16)
O1ⁱ—Cr1—N1	90.86 (19)	O1ⁱⁱ—Na1—O3ⁱⁱ	82.45 (16)
O1ⁱ—Cr1—N1ⁱ	87.12 (19)	O2ⁱⁱⁱ—Na1—O2ⁱ	124.4 (2)
O2—Cr1—O2ⁱ	88.56 (19)	O2ⁱⁱⁱ—Na1—O3	89.00 (17)
O2—Cr1—N1	82.2 (2)	O2ⁱⁱⁱ—Na1—O3ⁱⁱ	95.46 (17)
O2—Cr1—N1ⁱ	100.0 (2)	O2ⁱ—Na1—O3	95.46 (17)
O2ⁱ—Cr1—N1	100.0 (2)	O2ⁱ—Na1—O3ⁱⁱ	89.00 (17)
O2ⁱ—Cr1—N1ⁱ	82.2 (2)	O3—Na1—O3ⁱⁱ	170.4 (2)
N1—Cr1—N1ⁱ	177.1 (2)	Cr1—O1—Na1	99.77 (18)
O1—Na1—O1ⁱⁱ	107.84 (18)	Cr1—O2—Na1^iv	104.03 (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

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. Web of Science CrossRef CAS IUCr Journals Google Scholar
Burnett, M. N. & Johnson, C. K. (1996). ORTEPIII. Report ORNL-6895. Oak Ridge National Laboratory, Tennessee, USA. Google Scholar
Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan. Google Scholar
Mizuguchi, J., Sato, Y. & Uta, K. (2007a). Acta Cryst. E63, m1327–m1328. Web of Science CSD CrossRef IUCr Journals Google Scholar
Mizuguchi, J., Sato, Y. & Uta, K. (2007b). Acta Cryst. E63, m1377–m1378. Web of Science CSD CrossRef IUCr Journals Google Scholar
Mizuguchi, J., Sato, Y., Uta, K. & Sato, K. (2007). Acta Cryst. E63, o2509–o2510. Web of Science CSD CrossRef IUCr Journals Google Scholar
Mizuguchi, J., Uta, K. & Sato, Y. (2007). Acta Cryst. E63, m1329–m1330. Web of Science CSD CrossRef IUCr Journals Google Scholar
Rigaku (1998). PROCESS-AUTO. Rigaku Corporation, Tokyo, Japan. Google Scholar
Rigaku/MSC (2006). CrystalStructure. Version 3.8. Rigaku/MSC, The Woodlands, Texas, USA. Google Scholar
Sato, Y., Uta, K. & Mizuguchi, J. (2008). Acta Cryst. E64, m240–m241. Web of Science CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Tanaka, K. (1995). J. Electrostatics (Jpn. Version), 19, 15-21. Google Scholar
Yasumatsu, 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

doi:10.1107/S1600536808000433

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