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

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Bromido(quinolin-8-ol-κ2N,O)(quinolin-8-olato-κ2N,O)zinc(II) methanol monosolvate

aDepartment of Chemistry, General Campus, Shahid Beheshti University, Tehran 1983963113, Iran, and bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
*Correspondence e-mail: seikweng@um.edu.my

(Received 12 September 2010; accepted 14 September 2010; online 18 September 2010)

The title compound, [ZnBr(C9H6NO)(C9H7NO)]·CH3OH, has its metal atom N,O-chelated by a neutral and a deproton­ated 8-hy­droxy­quinoline ligand. The hy­droxy unit of the neutral ligand is a hydrogen-bond donor to the methanol O atom and the alk­oxy O atom of the monoanionic ligand is a hydrogen-bond acceptor to the methanol O atom. In the crystal, adjacent mol­ecules are linked by these two hydrogen bonds, generating a chain running along the a axis.

Related literature

For a related structure, see: Najafi et al. (2010[Najafi, E., Amini, M. M. & Ng, S. W. (2010). Acta Cryst. E66, m1276.]).

[Scheme 1]

Experimental

Crystal data
  • [ZnBr(C9H6NO)(C9H7NO)]·CH4O

  • Mr = 466.63

  • Triclinic, [P \overline 1]

  • a = 8.4485 (7) Å

  • b = 8.6968 (7) Å

  • c = 13.1868 (10) Å

  • α = 97.241 (1)°

  • β = 99.209 (1)°

  • γ = 109.470 (1)°

  • V = 884.81 (12) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 3.67 mm−1

  • T = 100 K

  • 0.30 × 0.20 × 0.10 mm

Data collection
  • Bruker SMART APEX diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.406, Tmax = 0.711

  • 8392 measured reflections

  • 4022 independent reflections

  • 3354 reflections with I > 2σ(I)

  • Rint = 0.028

Refinement
  • R[F2 > 2σ(F2)] = 0.032

  • wR(F2) = 0.103

  • S = 1.10

  • 4022 reflections

  • 237 parameters

  • H-atom parameters constrained

  • Δρmax = 0.78 e Å−3

  • Δρmin = −0.85 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O2—H2⋯O3i 0.84 1.90 2.585 (4) 137
O3—H3⋯O1 0.84 1.71 2.551 (4) 178
Symmetry code: (i) x-1, y, z.

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: X-SEED (Barbour, 2001[Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.]); software used to prepare material for publication: publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).

Supporting information


Comment top

An earlier study reported C10H10NO+.ZnBr2(C10H8NO).CH3OH, which feature cations, tetrahedral anions and solvent molecules linked by N···O, O···O and O···Br hydrogen bonds into a linear chain. The salt was synthesized by reacting zinc bromide and 2-methyl-8-hydroxyquinoline in methanol; no base was added (Najafi et al., 2010). The present study uses 8-hydoxyquinoline instead of 2-methy-8-hydroxyquinoline as the organic reactant. The product is a mono-solavated neutral molecule (Scheme I, Fig. 1). The methanol-solvated compound, ZnBr(C9H6NO)(C9H7NO).CH3OH, has its metal atom N,O-chelated by a neutral and deprotonated 8-hydroxyquinoline ligand. The hydroxy unit of the neutral ligand is hydrogen-bond donor methanol O atom and the alkoxy O atom of the monoanionic ligand is hydrogen-bond acceptor to methanol O atom. Adjacent molecules are linked by these two hydrogen bonds to generate a linear chain running along the a-axis of the triclinic unit cell (Fig. 2).

Related literature top

For a related structure, see: Najafi et al. (2010).

Experimental top

Zinc bromide (0.19 g, 0.75 mmol) and 8-hydroxyquinoline (0.22 g, 1.5 mmol) were loaded into a convection tube; the tube was filled with dry methanol and kept at 333 K. Crystals were collected from the side arm after several days.

Refinement top

Hydrogen atoms were placed in calculated positions (C–H 0.95–0.98, O–H 0.84 Å) and were included in the refinement in the riding model approximation, with U(H) set to 1.2–1.5Ueq(C,O).

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top
[Figure 1] Fig. 1. Anisotropic displacement ellipsoid plot (Barbour, 2001) of the title compound at the 70% probability level. Hydrogen atoms are drawn as spheres of arbitrary radius.
[Figure 2] Fig. 2. Hydrogen bonded chain structure.
Bromido(quinolin-8-ol-κ2N,O)(quinolin-8-olato- κ2N,O)zinc(II) methanol monosolvate top
Crystal data top
[ZnBr(C9H6NO)(C9H7NO)]·CH4OZ = 2
Mr = 466.63F(000) = 468
Triclinic, P1Dx = 1.751 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.4485 (7) ÅCell parameters from 3867 reflections
b = 8.6968 (7) Åθ = 2.5–28.2°
c = 13.1868 (10) ŵ = 3.67 mm1
α = 97.241 (1)°T = 100 K
β = 99.209 (1)°Prism, yellow
γ = 109.470 (1)°0.30 × 0.20 × 0.10 mm
V = 884.81 (12) Å3
Data collection top
Bruker SMART APEX
diffractometer
4022 independent reflections
Radiation source: fine-focus sealed tube3354 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.028
ω scansθmax = 27.5°, θmin = 2.5°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1010
Tmin = 0.406, Tmax = 0.711k = 1111
8392 measured reflectionsl = 1517
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.032Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.103H-atom parameters constrained
S = 1.10 w = 1/[σ2(Fo2) + (0.0457P)2 + 1.9422P]
where P = (Fo2 + 2Fc2)/3
4022 reflections(Δ/σ)max = 0.001
237 parametersΔρmax = 0.78 e Å3
0 restraintsΔρmin = 0.85 e Å3
Crystal data top
[ZnBr(C9H6NO)(C9H7NO)]·CH4Oγ = 109.470 (1)°
Mr = 466.63V = 884.81 (12) Å3
Triclinic, P1Z = 2
a = 8.4485 (7) ÅMo Kα radiation
b = 8.6968 (7) ŵ = 3.67 mm1
c = 13.1868 (10) ÅT = 100 K
α = 97.241 (1)°0.30 × 0.20 × 0.10 mm
β = 99.209 (1)°
Data collection top
Bruker SMART APEX
diffractometer
4022 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
3354 reflections with I > 2σ(I)
Tmin = 0.406, Tmax = 0.711Rint = 0.028
8392 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0320 restraints
wR(F2) = 0.103H-atom parameters constrained
S = 1.10Δρmax = 0.78 e Å3
4022 reflectionsΔρmin = 0.85 e Å3
237 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Zn10.45338 (5)0.64466 (5)0.71737 (3)0.01184 (12)
Br10.58054 (4)0.92415 (4)0.81357 (3)0.01654 (11)
O10.6864 (3)0.6465 (3)0.64187 (19)0.0152 (5)
O20.2092 (3)0.5306 (3)0.73396 (19)0.0145 (5)
H20.12300.54610.70240.022*
O30.9908 (3)0.6800 (3)0.7299 (2)0.0209 (6)
H30.89080.67070.70160.031*
N10.3868 (4)0.6687 (4)0.5653 (2)0.0119 (6)
N20.5025 (4)0.4869 (3)0.8093 (2)0.0121 (6)
C10.5180 (4)0.7280 (4)0.5148 (3)0.0110 (6)
C20.6796 (4)0.7212 (4)0.5573 (3)0.0128 (7)
C30.8163 (4)0.7842 (4)0.5120 (3)0.0150 (7)
H3A0.92550.78190.54150.018*
C40.7946 (5)0.8531 (5)0.4209 (3)0.0177 (7)
H40.88970.89500.38920.021*
C50.6384 (4)0.8603 (4)0.3777 (3)0.0151 (7)
H50.62640.90800.31720.018*
C60.4957 (5)0.7963 (4)0.4238 (3)0.0141 (7)
C70.3290 (5)0.7915 (4)0.3821 (3)0.0153 (7)
H70.30850.83500.32080.018*
C80.1969 (5)0.7238 (5)0.4304 (3)0.0173 (7)
H80.08350.71660.40200.021*
C90.2328 (4)0.6652 (4)0.5232 (3)0.0156 (7)
H90.14120.62080.55710.019*
C100.3596 (4)0.4025 (4)0.8429 (3)0.0109 (6)
C110.2035 (4)0.4283 (4)0.8012 (3)0.0138 (7)
C120.0569 (4)0.3427 (4)0.8339 (3)0.0150 (7)
H120.04810.35600.80740.018*
C130.0599 (5)0.2365 (5)0.9055 (3)0.0165 (7)
H130.04330.18000.92630.020*
C140.2083 (5)0.2119 (4)0.9464 (3)0.0165 (7)
H140.20790.14000.99510.020*
C150.3606 (4)0.2956 (4)0.9146 (3)0.0128 (7)
C160.5206 (5)0.2803 (4)0.9519 (3)0.0145 (7)
H160.52820.20850.99960.017*
C170.6636 (5)0.3682 (4)0.9194 (3)0.0153 (7)
H170.77160.36040.94570.018*
C180.6497 (4)0.4706 (4)0.8467 (3)0.0134 (7)
H180.74940.53010.82350.016*
C191.0704 (5)0.8335 (5)0.8036 (3)0.0271 (9)
H19A1.09330.81070.87430.041*
H19B0.99360.89670.80040.041*
H19C1.17890.89840.78670.041*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Zn10.0117 (2)0.0145 (2)0.0111 (2)0.00508 (15)0.00377 (15)0.00635 (15)
Br10.0208 (2)0.01368 (17)0.01481 (19)0.00510 (14)0.00314 (14)0.00568 (13)
O10.0162 (12)0.0189 (12)0.0138 (12)0.0078 (10)0.0056 (10)0.0078 (10)
O20.0105 (11)0.0194 (12)0.0163 (13)0.0080 (10)0.0012 (9)0.0076 (10)
O30.0130 (12)0.0228 (13)0.0256 (15)0.0072 (11)0.0002 (11)0.0035 (11)
N10.0106 (13)0.0158 (14)0.0101 (14)0.0054 (11)0.0026 (11)0.0030 (11)
N20.0159 (14)0.0129 (13)0.0080 (13)0.0037 (11)0.0045 (11)0.0049 (11)
C10.0104 (15)0.0115 (15)0.0109 (16)0.0041 (12)0.0033 (12)0.0001 (12)
C20.0159 (17)0.0138 (15)0.0117 (16)0.0083 (13)0.0044 (13)0.0042 (13)
C30.0115 (16)0.0187 (17)0.0171 (18)0.0080 (13)0.0034 (13)0.0043 (14)
C40.0172 (18)0.0193 (17)0.0155 (18)0.0026 (14)0.0076 (14)0.0052 (14)
C50.0169 (17)0.0161 (16)0.0107 (16)0.0044 (14)0.0015 (13)0.0030 (13)
C60.0185 (17)0.0126 (15)0.0114 (16)0.0046 (13)0.0061 (14)0.0027 (13)
C70.0180 (17)0.0180 (17)0.0099 (16)0.0072 (14)0.0003 (13)0.0043 (13)
C80.0159 (17)0.0236 (18)0.0126 (17)0.0076 (14)0.0010 (14)0.0061 (14)
C90.0120 (16)0.0209 (17)0.0161 (18)0.0077 (14)0.0045 (14)0.0045 (14)
C100.0124 (15)0.0120 (15)0.0089 (15)0.0056 (12)0.0025 (12)0.0011 (12)
C110.0145 (16)0.0158 (16)0.0118 (16)0.0062 (13)0.0025 (13)0.0034 (13)
C120.0108 (16)0.0208 (17)0.0123 (17)0.0054 (13)0.0003 (13)0.0038 (13)
C130.0146 (17)0.0199 (17)0.0152 (18)0.0041 (14)0.0063 (14)0.0062 (14)
C140.0206 (18)0.0153 (16)0.0152 (18)0.0056 (14)0.0069 (14)0.0066 (14)
C150.0151 (16)0.0123 (15)0.0082 (16)0.0029 (13)0.0004 (13)0.0002 (12)
C160.0197 (18)0.0145 (16)0.0127 (17)0.0105 (14)0.0021 (14)0.0048 (13)
C170.0143 (17)0.0208 (17)0.0127 (17)0.0093 (14)0.0009 (13)0.0043 (14)
C180.0121 (16)0.0171 (16)0.0143 (17)0.0081 (13)0.0049 (13)0.0045 (13)
C190.0193 (19)0.027 (2)0.029 (2)0.0051 (16)0.0007 (17)0.0014 (17)
Geometric parameters (Å, º) top
Zn1—O22.030 (2)C7—C81.372 (5)
Zn1—N22.040 (3)C7—H70.9500
Zn1—N12.050 (3)C8—C91.411 (5)
Zn1—O12.340 (2)C8—H80.9500
Zn1—Br12.3911 (5)C9—H90.9500
O1—C21.362 (4)C10—C151.409 (5)
O2—C111.328 (4)C10—C111.445 (5)
O2—H20.8400C11—C121.383 (5)
O3—C191.430 (5)C12—C131.404 (5)
O3—H30.8400C12—H120.9500
N1—C91.319 (4)C13—C141.378 (5)
N1—C11.372 (4)C13—H130.9500
N2—C181.322 (4)C14—C151.410 (5)
N2—C101.361 (4)C14—H140.9500
C1—C21.414 (5)C15—C161.417 (5)
C1—C61.418 (5)C16—C171.364 (5)
C2—C31.368 (5)C16—H160.9500
C3—C41.422 (5)C17—C181.406 (5)
C3—H3A0.9500C17—H170.9500
C4—C51.376 (5)C18—H180.9500
C4—H40.9500C19—H19A0.9800
C5—C61.416 (5)C19—H19B0.9800
C5—H50.9500C19—H19C0.9800
C6—C71.412 (5)
O2—Zn1—N282.51 (11)C6—C7—H7120.1
O2—Zn1—N195.88 (11)C7—C8—C9118.8 (3)
N2—Zn1—N1143.75 (11)C7—C8—H8120.6
O2—Zn1—O1150.98 (10)C9—C8—H8120.6
N2—Zn1—O190.06 (10)N1—C9—C8123.4 (3)
N1—Zn1—O173.91 (10)N1—C9—H9118.3
O2—Zn1—Br1112.41 (7)C8—C9—H9118.3
N2—Zn1—Br1109.66 (8)N2—C10—C15122.9 (3)
N1—Zn1—Br1104.40 (8)N2—C10—C11116.5 (3)
O1—Zn1—Br196.52 (6)C15—C10—C11120.7 (3)
C2—O1—Zn1108.4 (2)O2—C11—C12124.4 (3)
C11—O2—Zn1111.3 (2)O2—C11—C10118.4 (3)
C11—O2—H2124.4C12—C11—C10117.2 (3)
Zn1—O2—H2124.4C11—C12—C13121.4 (3)
C19—O3—H3109.5C11—C12—H12119.3
C9—N1—C1118.4 (3)C13—C12—H12119.3
C9—N1—Zn1122.8 (2)C14—C13—C12121.9 (3)
C1—N1—Zn1117.2 (2)C14—C13—H13119.0
C18—N2—C10119.0 (3)C12—C13—H13119.0
C18—N2—Zn1129.8 (2)C13—C14—C15118.6 (3)
C10—N2—Zn1110.8 (2)C13—C14—H14120.7
N1—C1—C2117.6 (3)C15—C14—H14120.7
N1—C1—C6122.0 (3)C10—C15—C14120.1 (3)
C2—C1—C6120.3 (3)C10—C15—C16116.4 (3)
O1—C2—C3124.0 (3)C14—C15—C16123.5 (3)
O1—C2—C1116.0 (3)C17—C16—C15120.2 (3)
C3—C2—C1119.9 (3)C17—C16—H16119.9
C2—C3—C4119.9 (3)C15—C16—H16119.9
C2—C3—H3A120.0C16—C17—C18119.3 (3)
C4—C3—H3A120.0C16—C17—H17120.4
C5—C4—C3121.2 (3)C18—C17—H17120.4
C5—C4—H4119.4N2—C18—C17122.2 (3)
C3—C4—H4119.4N2—C18—H18118.9
C4—C5—C6119.7 (3)C17—C18—H18118.9
C4—C5—H5120.2O3—C19—H19A109.5
C6—C5—H5120.2O3—C19—H19B109.5
C7—C6—C5123.5 (3)H19A—C19—H19B109.5
C7—C6—C1117.5 (3)O3—C19—H19C109.5
C5—C6—C1118.9 (3)H19A—C19—H19C109.5
C8—C7—C6119.8 (3)H19B—C19—H19C109.5
C8—C7—H7120.1
O2—Zn1—O1—C294.6 (3)C4—C5—C6—C7177.0 (3)
N2—Zn1—O1—C2169.1 (2)C4—C5—C6—C10.9 (5)
N1—Zn1—O1—C222.0 (2)N1—C1—C6—C74.1 (5)
Br1—Zn1—O1—C281.1 (2)C2—C1—C6—C7176.7 (3)
N2—Zn1—O2—C116.3 (2)N1—C1—C6—C5177.9 (3)
N1—Zn1—O2—C11149.9 (2)C2—C1—C6—C51.3 (5)
O1—Zn1—O2—C1182.7 (3)C5—C6—C7—C8178.5 (3)
Br1—Zn1—O2—C11101.9 (2)C1—C6—C7—C80.6 (5)
O2—Zn1—N1—C921.6 (3)C6—C7—C8—C92.0 (5)
N2—Zn1—N1—C9106.9 (3)C1—N1—C9—C81.9 (5)
O1—Zn1—N1—C9173.8 (3)Zn1—N1—C9—C8162.7 (3)
Br1—Zn1—N1—C993.4 (3)C7—C8—C9—N11.4 (6)
O2—Zn1—N1—C1173.6 (2)C18—N2—C10—C151.2 (5)
N2—Zn1—N1—C188.3 (3)Zn1—N2—C10—C15174.5 (3)
O1—Zn1—N1—C121.3 (2)C18—N2—C10—C11178.6 (3)
Br1—Zn1—N1—C171.4 (2)Zn1—N2—C10—C115.2 (4)
O2—Zn1—N2—C18178.6 (3)Zn1—O2—C11—C12175.2 (3)
N1—Zn1—N2—C1891.6 (3)Zn1—O2—C11—C105.4 (4)
O1—Zn1—N2—C1829.5 (3)N2—C10—C11—O20.1 (5)
Br1—Zn1—N2—C1867.5 (3)C15—C10—C11—O2179.8 (3)
O2—Zn1—N2—C106.2 (2)N2—C10—C11—C12179.6 (3)
N1—Zn1—N2—C1096.0 (3)C15—C10—C11—C120.7 (5)
O1—Zn1—N2—C10158.1 (2)O2—C11—C12—C13179.9 (3)
Br1—Zn1—N2—C10104.9 (2)C10—C11—C12—C130.7 (5)
C9—N1—C1—C2176.1 (3)C11—C12—C13—C140.2 (6)
Zn1—N1—C1—C218.4 (4)C12—C13—C14—C150.3 (5)
C9—N1—C1—C64.7 (5)N2—C10—C15—C14179.9 (3)
Zn1—N1—C1—C6160.8 (3)C11—C10—C15—C140.2 (5)
Zn1—O1—C2—C3161.4 (3)N2—C10—C15—C160.5 (5)
Zn1—O1—C2—C120.0 (3)C11—C10—C15—C16179.2 (3)
N1—C1—C2—O13.7 (4)C13—C14—C15—C100.3 (5)
C6—C1—C2—O1177.1 (3)C13—C14—C15—C16179.7 (3)
N1—C1—C2—C3177.7 (3)C10—C15—C16—C171.0 (5)
C6—C1—C2—C31.6 (5)C14—C15—C16—C17178.5 (3)
O1—C2—C3—C4177.1 (3)C15—C16—C17—C181.7 (5)
C1—C2—C3—C41.4 (5)C10—N2—C18—C170.4 (5)
C2—C3—C4—C51.0 (6)Zn1—N2—C18—C17172.3 (3)
C3—C4—C5—C60.8 (5)C16—C17—C18—N21.0 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2···O3i0.841.902.585 (4)137
O3—H3···O10.841.712.551 (4)178
Symmetry code: (i) x1, y, z.

Experimental details

Crystal data
Chemical formula[ZnBr(C9H6NO)(C9H7NO)]·CH4O
Mr466.63
Crystal system, space groupTriclinic, P1
Temperature (K)100
a, b, c (Å)8.4485 (7), 8.6968 (7), 13.1868 (10)
α, β, γ (°)97.241 (1), 99.209 (1), 109.470 (1)
V3)884.81 (12)
Z2
Radiation typeMo Kα
µ (mm1)3.67
Crystal size (mm)0.30 × 0.20 × 0.10
Data collection
DiffractometerBruker SMART APEX
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.406, 0.711
No. of measured, independent and
observed [I > 2σ(I)] reflections
8392, 4022, 3354
Rint0.028
(sin θ/λ)max1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.032, 0.103, 1.10
No. of reflections4022
No. of parameters237
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.78, 0.85

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2···O3i0.841.902.585 (4)137
O3—H3···O10.841.712.551 (4)178
Symmetry code: (i) x1, y, z.
 

Acknowledgements

We thank Shahid Beheshti University and the University of Malaya for supporting this study.

References

First citationBarbour, L. J. (2001). J. Supramol. Chem. 1, 189–191.  CrossRef CAS Google Scholar
First citationBruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationNajafi, E., Amini, M. M. & Ng, S. W. (2010). Acta Cryst. E66, m1276.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationSheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationWestrip, S. P. (2010). J. Appl. Cryst. 43, 920–925.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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