Bis[(5-bromo­pyridin-2-yl)methano­lato-κ2N,O]copper(II) monohydrate

Hamaguchi, T.; Kawahara, I.; Ando, I.

doi:10.1107/S1600536813026974

metal-organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 69| Part 11| November 2013| Page m585

doi:10.1107/S1600536813026974

Open

access

Bis[(5-bromopyridin-2-yl)methanolato-κ²N,O]copper(II) monohydrate

Tomohiko Hamaguchi,^a ^* Issei Kawahara ^a and Isao Ando ^a

^aDepartment of Chemistry, Faculty of Science, Fukuoka University, 8-19-1 Nanakuma, Jonan-ku, Fukuoka 814-0180, Japan
^*Correspondence e-mail: thama@fukuoka-u.ac.jp

(Received 22 September 2013; accepted 1 October 2013; online 5 October 2013)

In the title compound, [Cu(C₆H₅BrNO)₂]·H₂O, the Cu^II ion has a square-planer N₂O₂ coordination environment. Slipped π–π stackings [centroid-centroid distances: 3.625 (3), 3.767 (3), 3.935 (3) and 4.255 (3) Å] between pyridine rings and Cu⋯π interactions (centroid-to-Cu^II distance: 3.56 Å) between Cu²⁺ ions and pyridine rings lead to a layered arrangement parallel to (010). Intermolecular Br⋯O interactions [Br⋯O distances: 2.904 (3) and 3.042 (3) Å] and O—H⋯O hydrogen bonds form a three-dimensional network structure.

CCDC reference: 963946

Related literature

For bis(pyridin-2-ylmethanolato) complexes with four-coordinate Cu^II, see: Antonioli et al. (2007 ); Boyle et al. (2010 )

Experimental

Crystal data

[Cu(C₆H₅BrNO)₂]·H₂O
M_r = 455.60
Triclinic, $[P \overline 1]$
a = 7.1892 (9) Å
b = 7.5438 (9) Å
c = 13.2195 (15) Å
α = 99.338 (3)°
β = 103.334 (3)°
γ = 100.400 (3)°
V = 670.41 (14) Å³
Z = 2
Mo Kα radiation
μ = 7.60 mm⁻¹
T = 100 K
0.15 × 0.06 × 0.04 mm

Data collection

Rigaku R-AXIS RAPID diffractometer
Absorption correction: multi-scan (ABSCOR; Rigaku, 1995 ) T_min = 0.395, T_max = 0.751
6697 measured reflections
3074 independent reflections
2305 reflections with I > 2σ(I)
R_int = 0.039

Refinement

R[F² > 2σ(F²)] = 0.028
wR(F²) = 0.077
S = 1.20
3074 reflections
187 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 1.24 e Å⁻³
Δρ_min = −1.05 e Å⁻³

Table 1
Selected bond lengths (Å)

Cu1—O1	1.882 (3)
Cu1—O2	1.892 (3)
Cu1—N1	1.970 (3)
Cu1—N2	1.991 (3)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H11⋯O1	0.80 (2)	1.95 (2)	2.740 (4)	170 (6)
O3—H12⋯O2ⁱ	0.82 (2)	2.01 (2)	2.825 (4)	171 (5)
Symmetry code: (i) x, y+1, z.

Data collection: RAPID-AUTO (Rigaku, 2002 ); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Yadokari-XG 2009 (Wakita, 2001 ; Kabuto et al., 2009 ), Mercury (Macrae et al., 2006 ) and ORTEP-3 for Windows (Farrugia, 2012 ); software used to prepare material for publication: Yadokari-XG 2009 and publCIF (Westrip, 2010 ).

Supporting information

CCDC reference: 963946

Crystal structure: contains datablock I. DOI: 10.1107/S1600536813026974/ru2055sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813026974/ru2055Isup2.hkl

checkCIF report

Comment top

pyridin-2-ylmethanol is popular bidentate ligand, and many bis(pyridin-2-ylmethanolato) copper complexes are reported. The central copper ions of these complexes are mainly six- or five-coordinated; however, four-coordinated structure is few even in derivatives of pyridin-2-ylmethanol (Antonioli et al. (2007); Boyle et al. (2010)). Here, we report the crystal structure of [Cu^II(5-bromo-pyridin-2-ylmethanolato)₂]H₂O which has a square planner Cu^II ion. As depicted in Fig. 1, the Cu^II ion is coordinated by two bidentated 5-bromo-pyridin-2-ylmethanolato ligands. A torsion angle of N1—O1—N2—O2 is -12.8 (1) ° and the Cu^II ion is located at -0.013 (2) Å from N1—O1—N2—O2 mean plane; therefore, the Cu^II has a slightly distorted square planer coordination environment. The complexes are connected via slipped π-π stackings between pyridine ring and pyridine ring [centroid-to-centroid distances: 3.625 (3), 3.767 (3), 3.935 (3) and 4.255 (3) Å; interplanar distances: 3.425 (2), 3.319 (2), 3.303 (2) and 3.594 (2) Å] and Cu···π interaction (centroid-to-Cu^II distance: 3.56 Å). These connections make this complex two-dimensional layered structure along with a c plane. (Fig. 2) Intermolecular Br···O halogen interaction [Br···O distances: 2.904 (3) and 3.042 (3) Å] and OH···O hydrogen bondings [O···O distances: 2.740 (4) and 2.825 (4) Å] make this two-dimensional layer to three-dimensional structure. (Fig. 3)

Related literature top

For four-coordinated bis(pyridin-2-ylmethanolato) Cu^II complexes, see: Antonioli et al. (2007); Boyle et al. (2010)

For related literature, see: Burla et al. (2005).

Experimental top

A solution of triethylamine (0.125 mmol) in MeOH (0.5 ml) was added to a solution of 5-bromo-pyridin-2-ylmethanol (0.125 mmol) in MeOH (0.5 ml). A solution of CuSO₄·5H₂O (0.0625 mmol) in H₂O (0.25 ml) was added to the mixture. After several hours, purple crystals crystallized from the purple solution.

Computing details top

Data collection: RAPID-AUTO (Rigaku, 2002); cell refinement: RAPID-AUTO (Rigaku, 2002); data reduction: RAPID-AUTO (Rigaku, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Yadokari-XG 2009 (Wakita, 2001; Kabuto et al., 2009), Mercury (Bruno et al., 2002) and ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: Yadokari-XG 2009 (Wakita, 2001; Kabuto et al., 2009) and publCIF (Westrip, 2010).

Figures top

	Fig. 1. ORTEP drawing for the title complex with labeling showing 50% probability displacement ellipsoids.
	Fig. 2. Crystal packing of the complex. Pale purple spheres indicate centroids of pyridine rings and green dashed lines indicate π-π or Cu···π interactions. H₂O molecules are omitted for clarity. (blue: copper; red: oxygen; light blue: nitrogen; gray: carbon; brown: bromine; white: hydrogen)
	Fig. 3. Crystal packing of the complex. Light blue dashed lines indicate Br···O halogen interaction or OH···O hydrogen bonding.

Bis[(5-bromopyridin-2-yl)methanolato-κ²N,O]copper(II) monohydrate top

Crystal data top

[Cu(C₆H₅BrNO)₂]·H₂O	V = 670.41 (14) Å³
M_r = 455.60	Z = 2
Triclinic, P1	F(000) = 442
Hall symbol: -P 1	D_x = 2.257 Mg m⁻³
a = 7.1892 (9) Å	Mo Kα radiation, λ = 0.71075 Å
b = 7.5438 (9) Å	µ = 7.60 mm⁻¹
c = 13.2195 (15) Å	T = 100 K
α = 99.338 (3)°	Needle, purple
β = 103.334 (3)°	0.15 × 0.06 × 0.04 mm
γ = 100.400 (3)°

Data collection top

Rigaku R-AXIS RAPID diffractometer	2305 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.039
ω scans	θ_max = 27.5°, θ_min = 3.2°
Absorption correction: multi-scan (ABSCOR; Rigaku, 1995)	h = −9→9
T_min = 0.395, T_max = 0.751	k = −9→9
6697 measured reflections	l = −17→17
3074 independent reflections

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)] = 0.028	Hydrogen site location: mixed
wR(F²) = 0.077	H atoms treated by a mixture of independent and constrained refinement
S = 1.20	w = 1/[σ²(F_o²) + (0.0208P)² + 0.8098P] where P = (F_o² + 2F_c²)/3
3074 reflections	(Δ/σ)_max = 0.001
187 parameters	Δρ_max = 1.24 e Å⁻³
2 restraints	Δρ_min = −1.05 e Å⁻³

Crystal data top

[Cu(C₆H₅BrNO)₂]·H₂O	γ = 100.400 (3)°
M_r = 455.60	V = 670.41 (14) Å³
Triclinic, P1	Z = 2
a = 7.1892 (9) Å	Mo Kα radiation
b = 7.5438 (9) Å	µ = 7.60 mm⁻¹
c = 13.2195 (15) Å	T = 100 K
α = 99.338 (3)°	0.15 × 0.06 × 0.04 mm
β = 103.334 (3)°

Data collection top

Rigaku R-AXIS RAPID diffractometer	3074 independent reflections
Absorption correction: multi-scan (ABSCOR; Rigaku, 1995)	2305 reflections with I > 2σ(I)
T_min = 0.395, T_max = 0.751	R_int = 0.039
6697 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.028	2 restraints
wR(F²) = 0.077	H atoms treated by a mixture of independent and constrained refinement
S = 1.20	Δρ_max = 1.24 e Å⁻³
3074 reflections	Δρ_min = −1.05 e Å⁻³
187 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
Cu1	0.54156 (8)	0.45571 (7)	0.28991 (4)	0.01103 (13)
N1	0.6758 (5)	0.4606 (5)	0.4385 (3)	0.0113 (8)
N2	0.3724 (5)	0.4527 (5)	0.1470 (3)	0.0108 (7)
O1	0.6975 (4)	0.6960 (4)	0.3169 (2)	0.0158 (7)
O2	0.4262 (4)	0.2003 (4)	0.2603 (2)	0.0133 (6)
C1	0.7898 (6)	0.7701 (6)	0.4241 (3)	0.0113 (9)
H1	0.7220	0.8632	0.4510	0.014*
H2	0.9269	0.8337	0.4315	0.014*
C2	0.7909 (6)	0.6272 (6)	0.4907 (3)	0.0101 (8)
C3	0.8947 (7)	0.6571 (6)	0.5958 (4)	0.0149 (9)
H3	0.9752	0.7751	0.6315	0.018*
C4	0.8804 (7)	0.5124 (6)	0.6494 (3)	0.0146 (9)
H4	0.9514	0.5299	0.7218	0.017*
C5	0.7603 (6)	0.3425 (6)	0.5946 (3)	0.0128 (9)
C6	0.6600 (6)	0.3186 (6)	0.4895 (3)	0.0115 (9)
H5	0.5788	0.2016	0.4523	0.014*
C7	0.2809 (6)	0.1401 (6)	0.1650 (3)	0.0133 (9)
H6	0.1520	0.1080	0.1804	0.016*
H7	0.3032	0.0268	0.1249	0.016*
C8	0.2743 (6)	0.2825 (6)	0.0962 (3)	0.0117 (9)
C9	0.1745 (6)	0.2415 (6)	−0.0109 (3)	0.0126 (9)
H8	0.1095	0.1182	−0.0460	0.015*
C10	0.1710 (6)	0.3826 (6)	−0.0657 (4)	0.0149 (9)
H9	0.1049	0.3582	−0.1393	0.018*
C11	0.2666 (6)	0.5611 (6)	−0.0107 (3)	0.0119 (9)
C12	0.3689 (6)	0.5935 (6)	0.0947 (3)	0.0140 (10)
H10	0.4377	0.7152	0.1312	0.017*
Br1	0.72814 (7)	0.13936 (6)	0.66098 (3)	0.01408 (12)
Br2	0.26359 (6)	0.75716 (6)	−0.08331 (3)	0.01288 (12)
O3	0.7243 (5)	1.0111 (4)	0.2380 (3)	0.0190 (7)
H11	0.709 (8)	0.913 (4)	0.254 (4)	0.029*
H12	0.638 (6)	1.061 (7)	0.250 (4)	0.029*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.0139 (3)	0.0090 (3)	0.0090 (3)	0.0016 (2)	0.0019 (2)	0.0016 (2)
N1	0.0058 (18)	0.0174 (19)	0.0100 (19)	0.0017 (15)	0.0021 (15)	0.0018 (17)
N2	0.0138 (19)	0.0119 (17)	0.0065 (18)	0.0035 (15)	0.0013 (15)	0.0032 (15)
O1	0.0173 (17)	0.0136 (16)	0.0147 (17)	−0.0008 (13)	0.0010 (13)	0.0075 (14)
O2	0.0165 (17)	0.0100 (14)	0.0112 (16)	−0.0008 (12)	0.0018 (13)	0.0036 (13)
C1	0.008 (2)	0.011 (2)	0.013 (2)	−0.0007 (17)	0.0015 (18)	0.0038 (19)
C2	0.009 (2)	0.010 (2)	0.010 (2)	0.0011 (16)	0.0032 (17)	−0.0027 (18)
C3	0.017 (2)	0.012 (2)	0.015 (2)	0.0028 (18)	0.0054 (19)	0.000 (2)
C4	0.020 (2)	0.015 (2)	0.010 (2)	0.0040 (19)	0.0053 (19)	0.003 (2)
C5	0.013 (2)	0.015 (2)	0.015 (2)	0.0045 (18)	0.0074 (19)	0.009 (2)
C6	0.014 (2)	0.009 (2)	0.013 (2)	0.0048 (17)	0.0062 (19)	0.0014 (19)
C7	0.013 (2)	0.012 (2)	0.011 (2)	0.0014 (18)	−0.0016 (18)	0.0031 (19)
C8	0.008 (2)	0.010 (2)	0.015 (2)	0.0002 (16)	0.0024 (18)	0.0007 (19)
C9	0.009 (2)	0.014 (2)	0.015 (2)	0.0014 (17)	0.0026 (18)	0.0044 (19)
C10	0.013 (2)	0.019 (2)	0.010 (2)	0.0011 (18)	0.0019 (18)	0.000 (2)
C11	0.015 (2)	0.015 (2)	0.010 (2)	0.0060 (18)	0.0066 (18)	0.0070 (19)
C12	0.016 (2)	0.013 (2)	0.016 (2)	0.0065 (18)	0.008 (2)	0.003 (2)
Br1	0.0183 (2)	0.0142 (2)	0.0112 (2)	0.00372 (17)	0.00498 (18)	0.00535 (19)
Br2	0.0155 (2)	0.0128 (2)	0.0122 (2)	0.00431 (17)	0.00462 (17)	0.00519 (18)
O3	0.023 (2)	0.0137 (16)	0.0228 (19)	0.0039 (14)	0.0071 (15)	0.0083 (16)

Geometric parameters (Å, º) top

Cu1—O1	1.882 (3)	C4—H4	0.9500
Cu1—O2	1.892 (3)	C5—C6	1.375 (6)
Cu1—N1	1.970 (3)	C5—Br1	1.891 (4)
Cu1—N2	1.991 (3)	C6—H5	0.9500
N1—C2	1.349 (5)	C7—C8	1.516 (5)
N1—C6	1.356 (5)	C7—H6	0.9900
N2—C8	1.331 (5)	C7—H7	0.9900
N2—C12	1.359 (5)	C8—C9	1.387 (6)
O1—C1	1.391 (5)	C9—C10	1.383 (6)
O2—C7	1.385 (5)	C9—H8	0.9500
C1—C2	1.499 (5)	C10—C11	1.390 (6)
C1—H1	0.9900	C10—H9	0.9500
C1—H2	0.9900	C11—C12	1.376 (6)
C2—C3	1.378 (6)	C11—Br2	1.890 (4)
C3—C4	1.396 (6)	C12—H10	0.9500
C3—H3	0.9500	O3—H11	0.797 (19)
C4—C5	1.387 (6)	O3—H12	0.817 (19)

O1—Cu1—O2	169.72 (13)	C6—C5—C4	120.2 (4)
O1—Cu1—N1	84.45 (13)	C6—C5—Br1	118.3 (3)
O2—Cu1—N1	93.40 (13)	C4—C5—Br1	121.6 (3)
O1—Cu1—N2	98.13 (13)	N1—C6—C5	120.6 (4)
O2—Cu1—N2	85.38 (13)	N1—C6—H5	119.7
N1—Cu1—N2	171.91 (14)	C5—C6—H5	119.7
C2—N1—C6	120.1 (4)	O2—C7—C8	113.1 (3)
C2—N1—Cu1	113.1 (3)	O2—C7—H6	109.0
C6—N1—Cu1	126.8 (3)	C8—C7—H6	109.0
C8—N2—C12	119.8 (4)	O2—C7—H7	109.0
C8—N2—Cu1	111.6 (3)	C8—C7—H7	109.0
C12—N2—Cu1	127.9 (3)	H6—C7—H7	107.8
C1—O1—Cu1	113.9 (2)	N2—C8—C9	122.0 (4)
C7—O2—Cu1	113.5 (2)	N2—C8—C7	114.5 (4)
O1—C1—C2	112.8 (3)	C9—C8—C7	123.5 (4)
O1—C1—H1	109.0	C10—C9—C8	119.1 (4)
C2—C1—H1	109.0	C10—C9—H8	120.5
O1—C1—H2	109.0	C8—C9—H8	120.5
C2—C1—H2	109.0	C9—C10—C11	118.4 (4)
H1—C1—H2	107.8	C9—C10—H9	120.8
N1—C2—C3	121.3 (4)	C11—C10—H9	120.8
N1—C2—C1	113.6 (4)	C12—C11—C10	120.2 (4)
C3—C2—C1	125.1 (4)	C12—C11—Br2	120.4 (3)
C2—C3—C4	119.4 (4)	C10—C11—Br2	119.4 (3)
C2—C3—H3	120.3	N2—C12—C11	120.5 (4)
C4—C3—H3	120.3	N2—C12—H10	119.7
C5—C4—C3	118.5 (4)	C11—C12—H10	119.7
C5—C4—H4	120.8	H11—O3—H12	109 (5)
C3—C4—H4	120.8

O1—Cu1—N1—C2	6.8 (3)	C2—C3—C4—C5	−0.4 (6)
O2—Cu1—N1—C2	176.7 (3)	C3—C4—C5—C6	0.6 (6)
N2—Cu1—N1—C2	−102.2 (10)	C3—C4—C5—Br1	−178.9 (3)
O1—Cu1—N1—C6	−174.2 (3)	C2—N1—C6—C5	0.1 (6)
O2—Cu1—N1—C6	−4.3 (3)	Cu1—N1—C6—C5	−178.9 (3)
N2—Cu1—N1—C6	76.8 (11)	C4—C5—C6—N1	−0.5 (6)
O1—Cu1—N2—C8	165.7 (3)	Br1—C5—C6—N1	179.1 (3)
O2—Cu1—N2—C8	−4.6 (3)	Cu1—O2—C7—C8	11.3 (4)
N1—Cu1—N2—C8	−86.3 (10)	C12—N2—C8—C9	3.0 (6)
O1—Cu1—N2—C12	−5.0 (4)	Cu1—N2—C8—C9	−168.5 (3)
O2—Cu1—N2—C12	−175.2 (3)	C12—N2—C8—C7	−176.8 (3)
N1—Cu1—N2—C12	103.1 (10)	Cu1—N2—C8—C7	11.7 (4)
O2—Cu1—O1—C1	−91.0 (7)	O2—C7—C8—N2	−15.4 (5)
N1—Cu1—O1—C1	−12.7 (3)	O2—C7—C8—C9	164.8 (4)
N2—Cu1—O1—C1	159.6 (3)	N2—C8—C9—C10	−2.3 (6)
O1—Cu1—O2—C7	−114.6 (7)	C7—C8—C9—C10	177.5 (4)
N1—Cu1—O2—C7	167.8 (3)	C8—C9—C10—C11	−0.6 (6)
N2—Cu1—O2—C7	−4.2 (3)	C9—C10—C11—C12	2.8 (6)
Cu1—O1—C1—C2	15.9 (4)	C9—C10—C11—Br2	−179.8 (3)
C6—N1—C2—C3	0.2 (6)	C8—N2—C12—C11	−0.7 (6)
Cu1—N1—C2—C3	179.3 (3)	Cu1—N2—C12—C11	169.2 (3)
C6—N1—C2—C1	−178.9 (3)	C10—C11—C12—N2	−2.2 (6)
Cu1—N1—C2—C1	0.2 (4)	Br2—C11—C12—N2	−179.6 (3)
O1—C1—C2—N1	−10.3 (5)	N1—O1—N2—O2	−12.82 (13)
O1—C1—C2—C3	170.6 (4)	O1—N1—O2—N2	−13.32 (14)
N1—C2—C3—C4	0.0 (6)	N1—O2—N2—O1	11.80 (12)
C1—C2—C3—C4	179.0 (4)	O2—N1—O1—N2	11.96 (13)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H11···O1	0.80 (2)	1.95 (2)	2.740 (4)	170 (6)
O3—H12···O2ⁱ	0.82 (2)	2.01 (2)	2.825 (4)	171 (5)

Symmetry code: (i) x, y+1, z.

Selected bond lengths (Å) top

Cu1—O1	1.882 (3)	Cu1—N1	1.970 (3)
Cu1—O2	1.892 (3)	Cu1—N2	1.991 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H11···O1	0.797 (19)	1.95 (2)	2.740 (4)	170 (6)
O3—H12···O2ⁱ	0.817 (19)	2.01 (2)	2.825 (4)	171 (5)

Symmetry code: (i) x, y+1, z.

References

Antonioli, B., Bray, D. J., Clegg, J. K., Jolliffe, K. A., Gloe, K., Gloe, K. & Lindoy, L. F. (2007). Polyhedron, 26, 673–678. Web of Science CSD CrossRef CAS Google Scholar
Boyle, T. J., Ottley, L. M. & Raymond, R. (2010). J. Coord. Chem. 63, 545–557. Web of Science CSD CrossRef CAS Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Kabuto, C., Akine, S., Nemoto, T. & Kwon, E. (2009). J. Crystallogr. Soc. Jpn, 51, 218–224. CrossRef Google Scholar
Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453–457. Web of Science CrossRef CAS IUCr Journals Google Scholar
Rigaku (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan. Google Scholar
Rigaku (2002). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Wakita, K. (2001). Yadokari-XG. http://www.hat.hi-ho.ne.jp/k-wakita/yadokari . Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 69| Part 11| November 2013| Page m585

doi:10.1107/S1600536813026974

Open

access