Dichlorido[1-(8-quinolylimino­meth­yl)-2-naphtholato]iron(III)

Urakami, D.; Inoue, K.; Hayami, S.

doi:10.1107/S1600536809022880

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 7| July 2009| Page m800

doi:10.1107/S1600536809022880

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Dichlorido[1-(8-quinolyliminomethyl)-2-naphtholato]iron(III)

Daisuke Urakami,^a Katsuya Inoue ^a,^b and Shinya Hayami ^c ^*

^aDepartment of Chemistry, Graduate School of Science, Hiroshima University, Kagamiyama, Higashi–Hiroshima 739-8526, Japan, ^bDepartment of Chemistry and Institute for Advanced Materials Research, Hiroshima University, Kagamiyama, Higashi–Hiroshima 739-8526, Japan, and ^cDepartment of Chemistry, Graduate School of Science and Technology, Kumamoto University, Kurokami, Kumamoto 860-8555, Japan
^*Correspondence e-mail: hayami@sci.kumamoto-u.ac.jp

(Received 29 May 2009; accepted 15 June 2009; online 20 June 2009)

The Fe^III ion in the title complex, [FeCl₂(C₂₀H₁₃N₂O)], has a distorted square-pyramidal coordination formed by one O atom and two N atoms from a tridentate 1-(8-quinolyliminomethyl)-2-naphtholate ligand and two Cl atoms. In the crystal structure, molecules form a column structure along the a axis through π–π stacking interactions, with centroid–centroid distances of 3.657 (1) and 3.818 (2) Å. Weak C—H⋯Cl interactions are observed between the columns.

Related literature

For supramolecular self-assembly, see: Crivillers & Furukawa (2009 ).

Experimental

Crystal data

[FeCl₂(C₂₀H₁₃N₂O)]
M_r = 424.07
Monoclinic, P 2₁ /n
a = 7.6177 (5) Å
b = 18.5256 (11) Å
c = 12.2073 (7) Å
β = 91.1612 (16)°
V = 1722.37 (18) Å³
Z = 4
Mo Kα radiation
μ = 1.20 mm⁻¹
T = 293 K
0.80 × 0.20 × 0.10 mm

Data collection

Rigaku R-AXIS RAPID diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 2001 ) T_min = 0.448, T_max = 0.890
17621 measured reflections
3934 independent reflections
3182 reflections with I > 2σ(I)
R_int = 0.034

Refinement

R[F² > 2σ(F²)] = 0.037
wR(F²) = 0.090
S = 1.08
3934 reflections
235 parameters
H-atom parameters constrained
Δρ_max = 0.44 e Å⁻³
Δρ_min = −0.25 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C14—H12⋯Cl1ⁱ	0.93	2.81	3.598 (2)	143
C19—H8⋯Cl1ⁱⁱ	0.93	2.86	3.656 (2)	144
Symmetry codes: (i) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (ii) -x+1, -y, -z+1.

Data collection: PROCESS-AUTO (Rigaku, 1998 ); cell refinement: PROCESS-AUTO; data reduction: CrystalClear (Molecular Structure Corporation and Rigaku, 2002 ); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Yadokari–XG (Wakita, 2000 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809022880/is2429sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809022880/is2429Isup2.hkl

checkCIF report

Comment top

Self-assembly has been recognized as a most efficient process that organizes individual molecular components into highly ordered supramolecular species (Crivillers et al., 2009). The designed construction of supramolecules from molecular building blocks is noted as one of most challenging issues facing synthetic chemistry today. The method by using self-assembly is very important in developing novel molecular compounds with multi-functions. The cooperativity can be achieved by using π-π interactions as well as by using bridging ligands. We focused on a iron(III) complex with a qnal ligand [qnal = 1-(quinolin-8-yliminomethyl)-naphthalen-2-ol] having large π electron system. Here we report the synthesis and crystal structure of the title complex.

The Fe^III ion in the title complex, [Fe(qnal)Cl₂], has a distorted five coordination environment formed by one O atom and two N atoms from a qnal ligand, and two Cl atoms. The Fe—O bond length is shortest and the Fe—Cl bond length is longest. The π–π contacts between the benzene and pyridine rings, Cg1···Cg3ⁱ and Cg2···Cg3ⁱⁱ [symmetry codes: (i) -x, -y, 1 - z; (ii) 1 - x, -y, 1 - z, where Cg1, Cg2, Cg3 are centroids of the rings (N1/C1–C4/C9), (C4–C9) and (C11–/C15/C20), respectively] may stabilize the structure, with centroid-centroid distances of 3.657 (1) and 3.818 (2) Å, respectively. The molecules form a column structure by π-π stacking along the a axis. Three dimensional network is formed through C—H···Cl interactions between columns.

Related literature top

For supramolecular self-assembly, see: Crivillers & Furukawa (2009).

Experimental top

The ligand molecule, qnal, was prepared from 8-aminoquinoline (4.2 mg, 0.03 mmol) and 2-hydroxy-1-naphthaldehyde (5.1 mg, 0.03 mmol), which were mixed in 10 ml methanol and heating on a oil bath for about 2 h under reflux. The title complex was prepared by slow diffusion of qnal (9.0 mg, 0.03 mmol) and FeCl₃ (4.9 mg, 0.03 mmol) in methanol by using a H-form tube. After about one week, single crystals were obtained as black needles.

Computing details top

Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO (Rigaku, 1998); data reduction: CrystalClear (Molecular Structure Corporation and Rigaku, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Yadokari–XG (Wakita, 2000); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. ORTEP drawing of the title complex, showing 50% probability displacement ellipsoids.
	Fig. 2. Column structure for the title complex.
	Fig. 3. Part of the crystal structure, showing C—H···Cl interactions as dashed lines.

Dichlorido[1-(8-quinolyliminomethyl)-2-naphtholato]iron(III) top

Crystal data top

[FeCl₂(C₂₀H₁₃N₂O)]	F(000) = 860
M_r = 424.07	D_x = 1.635 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71075 Å
Hall symbol: -P 2yn	Cell parameters from 15565 reflections
a = 7.6177 (5) Å	θ = 3.1–27.7°
b = 18.5256 (11) Å	µ = 1.20 mm⁻¹
c = 12.2073 (7) Å	T = 293 K
β = 91.1612 (16)°	Needle, black
V = 1722.37 (18) Å³	0.80 × 0.20 × 0.10 mm
Z = 4

Data collection top

Rigaku R-AXIS RAPID diffractometer	3934 independent reflections
Radiation source: fine-focus sealed tube	3182 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.034
ω scans	θ_max = 27.5°, θ_min = 3.1°
Absorption correction: multi-scan (ABSCOR; Higashi, 2001)	h = −9→9
T_min = 0.448, T_max = 0.890	k = −24→23
17621 measured reflections	l = −15→15

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.090	H-atom parameters constrained
S = 1.08	w = 1/[σ²(F_o²) + (0.0395P)² + 0.7323P] where P = (F_o² + 2F_c²)/3
3934 reflections	(Δ/σ)_max = 0.001
235 parameters	Δρ_max = 0.44 e Å⁻³
0 restraints	Δρ_min = −0.25 e Å⁻³

Crystal data top

[FeCl₂(C₂₀H₁₃N₂O)]	V = 1722.37 (18) Å³
M_r = 424.07	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 7.6177 (5) Å	µ = 1.20 mm⁻¹
b = 18.5256 (11) Å	T = 293 K
c = 12.2073 (7) Å	0.80 × 0.20 × 0.10 mm
β = 91.1612 (16)°

Data collection top

Rigaku R-AXIS RAPID diffractometer	3934 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi, 2001)	3182 reflections with I > 2σ(I)
T_min = 0.448, T_max = 0.890	R_int = 0.034
17621 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	0 restraints
wR(F²) = 0.090	H-atom parameters constrained
S = 1.08	Δρ_max = 0.44 e Å⁻³
3934 reflections	Δρ_min = −0.25 e Å⁻³
235 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
Fe1	0.16122 (4)	0.072865 (16)	0.67792 (2)	0.03433 (11)
C1	0.1279 (3)	−0.04180 (15)	0.8607 (2)	0.0498 (6)
H1	0.0834	−0.0042	0.9022	0.060*
C2	0.1519 (4)	−0.10907 (17)	0.9103 (2)	0.0599 (7)
H2	0.1216	−0.1161	0.9830	0.072*
C3	0.2195 (4)	−0.16364 (16)	0.8515 (2)	0.0562 (7)
H3	0.2361	−0.2086	0.8839	0.067*
C4	0.2653 (3)	−0.15321 (13)	0.74142 (19)	0.0409 (5)
C5	0.3412 (3)	−0.20622 (12)	0.6755 (2)	0.0485 (6)
H4	0.3632	−0.2521	0.7035	0.058*
C6	0.3825 (3)	−0.19030 (12)	0.5702 (2)	0.0451 (6)
H5	0.4356	−0.2254	0.5276	0.054*
C7	0.3470 (3)	−0.12257 (12)	0.52462 (19)	0.0401 (5)
H6	0.3743	−0.1136	0.4520	0.048*
C8	0.2723 (3)	−0.06922 (10)	0.58598 (17)	0.0306 (4)
C9	0.2340 (3)	−0.08413 (11)	0.69642 (17)	0.0329 (4)
C10	0.2480 (3)	0.01983 (11)	0.44882 (17)	0.0321 (4)
H7	0.2835	−0.0167	0.4020	0.038*
C11	0.2188 (3)	0.08832 (11)	0.40091 (17)	0.0327 (4)
C12	0.1502 (3)	0.14570 (12)	0.46229 (19)	0.0399 (5)
C13	0.1253 (3)	0.21425 (13)	0.4125 (2)	0.0495 (6)
H13	0.0767	0.2516	0.4526	0.059*
C14	0.1709 (3)	0.22598 (14)	0.3084 (2)	0.0524 (7)
H12	0.1570	0.2719	0.2789	0.063*
C15	0.2392 (3)	0.17054 (13)	0.24256 (19)	0.0441 (6)
C16	0.2835 (4)	0.18369 (17)	0.1329 (2)	0.0600 (8)
H11	0.2733	0.2303	0.1052	0.072*
C17	0.3403 (4)	0.13057 (19)	0.0673 (2)	0.0655 (8)
H10	0.3656	0.1400	−0.0055	0.079*
C18	0.3606 (4)	0.06130 (17)	0.1099 (2)	0.0586 (7)
H9	0.3989	0.0244	0.0647	0.070*
C19	0.3254 (3)	0.04645 (14)	0.21726 (19)	0.0450 (6)
H8	0.3441	0.0001	0.2444	0.054*
C20	0.2612 (3)	0.10040 (12)	0.28673 (18)	0.0354 (5)
N1	0.1657 (2)	−0.02918 (10)	0.75694 (14)	0.0366 (4)
N2	0.2306 (2)	0.00218 (9)	0.55195 (14)	0.0305 (4)
O1	0.1072 (3)	0.13872 (9)	0.56416 (14)	0.0559 (5)
Cl1	0.40989 (8)	0.11675 (4)	0.74667 (6)	0.05373 (18)
Cl2	−0.06535 (9)	0.11031 (4)	0.77771 (7)	0.0629 (2)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Fe1	0.03643 (18)	0.03247 (18)	0.03430 (17)	0.00072 (13)	0.00555 (13)	−0.00741 (13)
C1	0.0496 (15)	0.0636 (17)	0.0365 (12)	−0.0030 (13)	0.0074 (11)	0.0006 (12)
C2	0.0656 (18)	0.076 (2)	0.0387 (14)	−0.0091 (16)	0.0045 (13)	0.0150 (14)
C3	0.0592 (17)	0.0552 (16)	0.0539 (15)	−0.0136 (13)	−0.0071 (13)	0.0222 (13)
C4	0.0372 (12)	0.0376 (12)	0.0476 (13)	−0.0079 (10)	−0.0082 (10)	0.0090 (10)
C5	0.0510 (15)	0.0290 (12)	0.0650 (16)	−0.0031 (11)	−0.0136 (13)	0.0054 (11)
C6	0.0474 (14)	0.0306 (11)	0.0569 (15)	0.0025 (10)	−0.0076 (12)	−0.0099 (10)
C7	0.0459 (13)	0.0345 (12)	0.0400 (12)	0.0007 (10)	0.0006 (10)	−0.0067 (9)
C8	0.0299 (10)	0.0264 (10)	0.0354 (11)	−0.0023 (8)	−0.0013 (8)	−0.0019 (8)
C9	0.0282 (10)	0.0336 (11)	0.0367 (11)	−0.0055 (9)	−0.0026 (8)	0.0006 (9)
C10	0.0328 (11)	0.0313 (11)	0.0322 (10)	0.0007 (9)	0.0034 (8)	−0.0047 (8)
C11	0.0314 (11)	0.0317 (11)	0.0348 (11)	−0.0002 (9)	−0.0015 (9)	−0.0010 (8)
C12	0.0397 (12)	0.0377 (12)	0.0420 (12)	0.0075 (10)	−0.0076 (10)	−0.0035 (10)
C13	0.0530 (15)	0.0365 (13)	0.0583 (16)	0.0138 (11)	−0.0138 (12)	−0.0061 (11)
C14	0.0528 (16)	0.0383 (13)	0.0654 (18)	0.0043 (11)	−0.0165 (13)	0.0139 (12)
C15	0.0390 (13)	0.0461 (14)	0.0466 (13)	−0.0034 (11)	−0.0099 (10)	0.0126 (11)
C16	0.0582 (17)	0.0689 (19)	0.0525 (16)	−0.0071 (15)	−0.0085 (14)	0.0291 (14)
C17	0.0636 (19)	0.092 (2)	0.0408 (14)	−0.0143 (17)	0.0042 (13)	0.0187 (15)
C18	0.0532 (16)	0.080 (2)	0.0431 (14)	−0.0083 (14)	0.0114 (12)	−0.0013 (14)
C19	0.0465 (14)	0.0495 (14)	0.0391 (12)	−0.0061 (11)	0.0077 (11)	0.0021 (11)
C20	0.0307 (11)	0.0381 (11)	0.0372 (11)	−0.0044 (9)	−0.0033 (9)	0.0049 (9)
N1	0.0371 (10)	0.0410 (10)	0.0317 (9)	−0.0036 (8)	0.0040 (8)	−0.0004 (8)
N2	0.0339 (9)	0.0276 (8)	0.0301 (9)	0.0004 (7)	0.0020 (7)	−0.0019 (7)
O1	0.0798 (13)	0.0474 (10)	0.0406 (9)	0.0282 (9)	0.0024 (9)	−0.0061 (8)
Cl1	0.0437 (3)	0.0501 (4)	0.0674 (4)	−0.0116 (3)	0.0018 (3)	−0.0121 (3)
Cl2	0.0552 (4)	0.0489 (4)	0.0858 (5)	0.0031 (3)	0.0354 (4)	−0.0098 (3)

Geometric parameters (Å, º) top

Fe1—O1	1.8876 (17)	C9—N1	1.367 (3)
Fe1—N2	2.0957 (17)	C10—C11	1.413 (3)
Fe1—N1	2.1223 (19)	C10—N2	1.310 (3)
Fe1—Cl1	2.2111 (7)	C10—H7	0.9300
Fe1—Cl2	2.2426 (7)	C11—C12	1.407 (3)
C1—C2	1.396 (4)	C11—C20	1.454 (3)
C1—N1	1.325 (3)	C12—C13	1.419 (3)
C1—H1	0.9300	C12—O1	1.299 (3)
C2—C3	1.349 (4)	C13—C14	1.342 (4)
C2—H2	0.9300	C13—H13	0.9300
C3—C4	1.408 (3)	C14—C15	1.410 (4)
C3—H3	0.9300	C14—H12	0.9300
C4—C5	1.402 (3)	C15—C16	1.408 (4)
C4—C9	1.411 (3)	C15—C20	1.416 (3)
C5—C6	1.362 (4)	C16—C17	1.346 (4)
C5—H4	0.9300	C16—H11	0.9300
C6—H5	0.9300	C17—H10	0.9300
C6—C7	1.397 (3)	C18—C17	1.392 (4)
C7—C8	1.371 (3)	C18—H9	0.9300
C7—H6	0.9300	C19—C18	1.371 (3)
C8—C9	1.412 (3)	C19—H8	0.9300
C8—N2	1.420 (3)	C20—C19	1.405 (3)

Fe1—N1—C1	126.14 (17)	C11—C20—C15	118.6 (2)
Fe1—N1—C9	114.86 (14)	C11—C20—C19	123.8 (2)
Fe1—N2—C8	115.18 (13)	C12—C11—C20	119.1 (2)
Fe1—N2—C10	125.53 (14)	C12—C13—H13	119.5
Fe1—O1—C12	135.52 (15)	C13—C12—O1	117.7 (2)
C1—C2—C3	119.1 (2)	C13—C14—C15	121.8 (2)
C1—C2—H2	120.5	C13—C14—H12	119.1
C1—N1—C9	118.5 (2)	C14—C13—C12	121.1 (2)
C2—C1—N1	122.9 (3)	C14—C13—H13	119.5
C2—C1—H1	118.5	C14—C15—C20	119.6 (2)
C2—C3—C4	120.7 (2)	C15—C14—H12	119.1
C2—C3—H3	119.7	C15—C16—H11	119.2
C3—C2—H2	120.5	C15—C20—C19	117.6 (2)
C3—C4—C5	124.4 (2)	C16—C15—C14	120.9 (2)
C3—C4—C9	116.9 (2)	C16—C15—C20	119.5 (2)
C4—C3—H3	119.7	C16—C17—C18	119.1 (3)
C4—C5—C6	119.8 (2)	C16—C17—H10	120.4
C4—C5—H4	120.1	C17—C16—C15	121.7 (3)
C4—C9—C8	120.8 (2)	C17—C16—H11	119.2
C4—C9—N1	121.9 (2)	C17—C18—C19	121.3 (3)
C5—C4—C9	118.7 (2)	C17—C18—H9	119.3
C5—C6—C7	121.6 (2)	C18—C17—H10	120.4
C5—C6—H5	119.2	C18—C19—C20	120.8 (3)
C6—C5—H4	120.1	C18—C19—H8	119.6
C6—C7—C8	120.6 (2)	C19—C18—H9	119.3
C6—C7—H6	119.7	C20—C19—H8	119.6
C7—C6—H5	119.2	N1—Fe1—N2	77.00 (7)
C7—C8—C9	118.47 (19)	N1—Fe1—O1	155.70 (8)
C7—C8—N2	127.17 (19)	N1—Fe1—Cl1	98.59 (5)
C8—C7—H6	119.7	N1—Fe1—Cl2	91.95 (5)
C8—C9—N1	117.29 (19)	N1—C1—H1	118.5
C8—N2—C10	119.16 (17)	N2—Fe1—O1	85.32 (7)
C9—C8—N2	114.34 (18)	N2—Fe1—Cl1	106.34 (5)
C10—C11—C12	121.0 (2)	N2—Fe1—Cl2	143.16 (5)
C10—C11—C20	119.91 (19)	N2—C10—H7	116.4
C11—C10—N2	127.14 (19)	O1—Fe1—Cl1	102.35 (7)
C11—C10—H7	116.4	O1—Fe1—Cl2	92.36 (6)
C11—C12—C13	119.7 (2)	Cl1—Fe1—Cl2	110.06 (3)
C11—C12—O1	122.6 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C14—H12···Cl1ⁱ	0.93	2.81	3.598 (2)	143
C19—H8···Cl1ⁱⁱ	0.93	2.86	3.656 (2)	144

Symmetry codes: (i) x−1/2, −y+1/2, z−1/2; (ii) −x+1, −y, −z+1.

Experimental details

Crystal data
Chemical formula	[FeCl₂(C₂₀H₁₃N₂O)]
M_r	424.07
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	293
a, b, c (Å)	7.6177 (5), 18.5256 (11), 12.2073 (7)
β (°)	91.1612 (16)
V (Å³)	1722.37 (18)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.20
Crystal size (mm)	0.80 × 0.20 × 0.10

Data collection
Diffractometer	Rigaku R-AXIS RAPID diffractometer
Absorption correction	Multi-scan (ABSCOR; Higashi, 2001)
T_min, T_max	0.448, 0.890
No. of measured, independent and observed [I > 2σ(I)] reflections	17621, 3934, 3182
R_int	0.034
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.090, 1.08
No. of reflections	3934
No. of parameters	235
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.44, −0.25

Computer programs: PROCESS-AUTO (Rigaku, 1998), CrystalClear (Molecular Structure Corporation and Rigaku, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), Yadokari–XG (Wakita, 2000).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C14—H12···Cl1ⁱ	0.93	2.81	3.598 (2)	143
C19—H8···Cl1ⁱⁱ	0.93	2.86	3.656 (2)	144

Symmetry codes: (i) x−1/2, −y+1/2, z−1/2; (ii) −x+1, −y, −z+1.

Acknowledgements

This work was supported by `Development of Molecular Devices in Ferroelectric Metallomesogens' in 2006 of the New Energy and Industrial Technology Development Organization (NEDO) of Japan and Grants-in-Aid for Scientific Research from the Ministry of Education, Culture, Sports, Science and Technology of the Japanese Governement (No. 20350028).

References

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