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8-Hy­dr­oxy-2-methyl­quinolinium di­iodido(2-methyl­quinolin-8-olato-κ2N,O)zincate(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 anion of the title salt, (C10H10NO)[Zn(C10H8NO)I2]·CH3OH, has its metal atom N,O-chelated by the deprotonated 2-methyl-8-hy­droxy­quinoline ligand. The hy­droxy unit of the cation is a hydrogen-bond donor to the alkoxide O atom of the tetra­hedrally coordinated anion, whereas the ammonium cation acts as a hydrogen-bond donor to the methano­lic O atom. In the crystal, adjacent ion pairs and solvent mol­ecules are linked by a methanol–halogen O—H⋯I hydrogen bond, generating a chain running along the a axis.

Related literature

For the isostructural chloro analog, see: Sattarzadeh et al. (2009[Sattarzadeh, E., Mohammadnezhad, G., Amini, M. M. & Ng, S. W. (2009). Acta Cryst. E65, m553.]).

[Scheme 1]

Experimental

Crystal data
  • (C10H10NO)[Zn(C10H8NO)I2]·CH4O

  • Mr = 669.58

  • Monoclinic, P 21 /n

  • a = 10.1745 (6) Å

  • b = 14.6292 (9) Å

  • c = 16.5321 (10) Å

  • β = 106.356 (1)°

  • V = 2361.1 (2) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 3.68 mm−1

  • T = 295 K

  • 0.35 × 0.25 × 0.15 mm

Data collection
  • Bruker SMART APEX diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.359, Tmax = 0.608

  • 21863 measured reflections

  • 5404 independent reflections

  • 4049 reflections with I > 2σ(I)

  • Rint = 0.031

Refinement
  • R[F2 > 2σ(F2)] = 0.031

  • wR(F2) = 0.090

  • S = 1.06

  • 5404 reflections

  • 267 parameters

  • H-atom parameters constrained

  • Δρmax = 0.73 e Å−3

  • Δρmin = −0.78 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O2—H2⋯O1 0.82 1.74 2.559 (4) 172
O3—H3⋯I1i 0.82 2.88 3.575 (4) 144
N2—H2n⋯O3 0.86 1.92 2.757 (5) 165
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+.ZnCI2(C10H8NO).CH3OH, which feature cations, tetrahedral anions and solvent molecules linked by N···O, O···O and O···Cl hydrogen bonds into a linear chain (Sattarzadeh et al., 2009). The present iodide analog (Scheme I, Fig. 1) is isostructural, the two compounds displaying matching cell dimensions. The hydroxy unit of the cation is hydrogen-bond donor to the alkoxide O atom of the tetrahedrally coordinated anion whereas the ammonium unit is hydrogen-bond donor to the methanolic O atom. Adjacent ion-pairs and solvent molecules are linked by a O–Hmethanol···I hydrogen bond to generate a linear chain running along the a-axis of the monoclinic unit cell.

Related literature top

For the isostructural chloro analog, see: Sattarzadeh et al. (2009).

Experimental top

Zinc iodide (0.24 g, 0.75 mmol) and 2-methyl-8-hydroxyquinoline (0.24 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 0.93–0.96, N–H 0.86 and O–H 0.82 Å) and were included in the refinement in the riding model approximation, with U(H) set to 1.2–1.5Ueq(C,N,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 50% probability level. Hydrogen atoms are drawn as spheres of arbitrary radius.
8-Hydroxy-2-methylquinolinium diiodido(2-methylquinolin-8-olato-κ2N,O)zincate(II) methanol monosolvate top
Crystal data top
(C10H10NO)[Zn(C10H8NO)I2]·CH4OF(000) = 1288
Mr = 669.58Dx = 1.884 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 6864 reflections
a = 10.1745 (6) Åθ = 2.5–25.1°
b = 14.6292 (9) ŵ = 3.68 mm1
c = 16.5321 (10) ÅT = 295 K
β = 106.356 (1)°Triangular block, yellow
V = 2361.1 (2) Å30.35 × 0.25 × 0.15 mm
Z = 4
Data collection top
Bruker SMART APEX
diffractometer
5404 independent reflections
Radiation source: fine-focus sealed tube4049 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.031
ω scansθmax = 27.5°, θmin = 1.9°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1313
Tmin = 0.359, Tmax = 0.608k = 1919
21863 measured reflectionsl = 2118
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)] = 0.031Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.090H-atom parameters constrained
S = 1.06 w = 1/[σ2(Fo2) + (0.0352P)2 + 2.9232P]
where P = (Fo2 + 2Fc2)/3
5404 reflections(Δ/σ)max = 0.001
267 parametersΔρmax = 0.73 e Å3
0 restraintsΔρmin = 0.78 e Å3
Crystal data top
(C10H10NO)[Zn(C10H8NO)I2]·CH4OV = 2361.1 (2) Å3
Mr = 669.58Z = 4
Monoclinic, P21/nMo Kα radiation
a = 10.1745 (6) ŵ = 3.68 mm1
b = 14.6292 (9) ÅT = 295 K
c = 16.5321 (10) Å0.35 × 0.25 × 0.15 mm
β = 106.356 (1)°
Data collection top
Bruker SMART APEX
diffractometer
5404 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
4049 reflections with I > 2σ(I)
Tmin = 0.359, Tmax = 0.608Rint = 0.031
21863 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0310 restraints
wR(F2) = 0.090H-atom parameters constrained
S = 1.06Δρmax = 0.73 e Å3
5404 reflectionsΔρmin = 0.78 e Å3
267 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
I10.99864 (3)0.22364 (2)0.185681 (19)0.05940 (11)
I21.12403 (4)0.50224 (2)0.22894 (2)0.06773 (12)
Zn10.98601 (5)0.37087 (4)0.26758 (3)0.04947 (13)
O10.7946 (3)0.4058 (2)0.25987 (17)0.0590 (8)
O20.5880 (3)0.3620 (2)0.13701 (17)0.0575 (8)
H20.65560.37980.17360.086*
O30.3218 (4)0.2893 (5)0.1583 (3)0.132 (2)
H30.24240.30080.15730.198*
N11.0064 (3)0.3664 (2)0.39435 (19)0.0421 (7)
N20.3603 (3)0.3482 (2)0.0082 (2)0.0464 (8)
H2N0.36200.33460.05910.056*
C10.8857 (4)0.3933 (3)0.4085 (2)0.0439 (9)
C20.7747 (4)0.4140 (3)0.3364 (2)0.0491 (10)
C30.6530 (5)0.4435 (3)0.3495 (3)0.0585 (11)
H3a0.57940.45870.30360.070*
C40.6399 (5)0.4505 (4)0.4314 (3)0.0675 (13)
H40.55680.46990.43860.081*
C50.7444 (5)0.4301 (3)0.5007 (3)0.0639 (13)
H50.73250.43500.55430.077*
C60.8711 (5)0.4016 (3)0.4906 (3)0.0507 (10)
C70.9878 (5)0.3799 (3)0.5575 (3)0.0611 (13)
H70.98310.38340.61280.073*
C81.1066 (5)0.3541 (3)0.5424 (3)0.0585 (12)
H81.18280.34070.58720.070*
C91.1151 (4)0.3477 (3)0.4589 (2)0.0481 (9)
C101.2444 (5)0.3205 (3)0.4395 (3)0.0625 (12)
H10A1.27970.37170.41590.094*
H10B1.22600.27100.39980.094*
H10C1.31070.30140.49040.094*
C110.4800 (4)0.3758 (3)0.0072 (2)0.0423 (8)
C120.6010 (4)0.3837 (3)0.0609 (2)0.0445 (9)
C130.7190 (4)0.4124 (3)0.0438 (3)0.0487 (9)
H130.79980.41730.08730.058*
C140.7184 (5)0.4343 (3)0.0388 (3)0.0558 (11)
H140.79910.45410.04880.067*
C150.6026 (5)0.4273 (3)0.1051 (3)0.0548 (11)
H150.60490.44170.15940.066*
C160.4804 (4)0.3981 (3)0.0899 (2)0.0461 (9)
C170.3539 (5)0.3907 (3)0.1537 (3)0.0564 (11)
H170.35010.40490.20910.068*
C180.2383 (5)0.3632 (3)0.1349 (3)0.0571 (11)
H180.15640.35880.17760.069*
C190.2415 (4)0.3414 (3)0.0518 (3)0.0542 (11)
C200.1160 (5)0.3133 (4)0.0273 (4)0.0782 (16)
H20A0.11300.34550.02270.117*
H20B0.11890.24870.01680.117*
H20C0.03580.32770.07230.117*
C210.3972 (6)0.2771 (4)0.2385 (3)0.0768 (15)
H21A0.49200.27170.24040.115*
H21B0.36800.22240.26050.115*
H21C0.38530.32860.27180.115*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
I10.06369 (19)0.0647 (2)0.04850 (17)0.01375 (14)0.01360 (13)0.00404 (13)
I20.0790 (2)0.0597 (2)0.0736 (2)0.00371 (16)0.03639 (18)0.00974 (15)
Zn10.0457 (3)0.0681 (3)0.0332 (2)0.0018 (2)0.00879 (19)0.0042 (2)
O10.0437 (16)0.099 (2)0.0323 (14)0.0011 (16)0.0070 (12)0.0026 (15)
O20.0492 (17)0.085 (2)0.0346 (15)0.0055 (16)0.0053 (12)0.0056 (15)
O30.058 (2)0.279 (7)0.061 (3)0.008 (3)0.022 (2)0.046 (3)
N10.0462 (18)0.0456 (18)0.0308 (15)0.0052 (14)0.0046 (13)0.0035 (13)
N20.0467 (19)0.0472 (19)0.0412 (18)0.0031 (15)0.0057 (15)0.0036 (15)
C10.052 (2)0.045 (2)0.0345 (19)0.0133 (17)0.0110 (17)0.0016 (16)
C20.048 (2)0.061 (3)0.039 (2)0.0094 (19)0.0128 (18)0.0015 (18)
C30.054 (3)0.067 (3)0.055 (3)0.003 (2)0.016 (2)0.003 (2)
C40.063 (3)0.079 (3)0.070 (3)0.005 (3)0.034 (3)0.011 (3)
C50.083 (4)0.067 (3)0.051 (3)0.012 (3)0.034 (3)0.006 (2)
C60.070 (3)0.045 (2)0.038 (2)0.013 (2)0.018 (2)0.0007 (17)
C70.092 (4)0.060 (3)0.030 (2)0.016 (3)0.015 (2)0.0013 (19)
C80.075 (3)0.054 (3)0.036 (2)0.005 (2)0.001 (2)0.0066 (19)
C90.057 (2)0.043 (2)0.039 (2)0.0060 (18)0.0048 (18)0.0027 (17)
C100.060 (3)0.065 (3)0.052 (3)0.003 (2)0.000 (2)0.003 (2)
C110.047 (2)0.038 (2)0.040 (2)0.0055 (16)0.0097 (17)0.0019 (16)
C120.049 (2)0.048 (2)0.036 (2)0.0058 (17)0.0106 (17)0.0007 (16)
C130.042 (2)0.057 (2)0.044 (2)0.0040 (18)0.0080 (17)0.0008 (19)
C140.056 (3)0.059 (3)0.057 (3)0.003 (2)0.024 (2)0.001 (2)
C150.066 (3)0.059 (3)0.043 (2)0.010 (2)0.019 (2)0.0031 (19)
C160.055 (2)0.044 (2)0.038 (2)0.0074 (18)0.0093 (18)0.0044 (16)
C170.069 (3)0.058 (3)0.036 (2)0.009 (2)0.005 (2)0.0038 (19)
C180.053 (3)0.063 (3)0.047 (2)0.004 (2)0.001 (2)0.006 (2)
C190.049 (2)0.051 (2)0.054 (3)0.0018 (19)0.000 (2)0.001 (2)
C200.050 (3)0.098 (4)0.079 (4)0.011 (3)0.006 (3)0.014 (3)
C210.078 (4)0.085 (4)0.069 (3)0.002 (3)0.022 (3)0.023 (3)
Geometric parameters (Å, º) top
I1—Zn12.5665 (6)C8—H80.9300
I2—Zn12.5649 (6)C9—C101.493 (6)
Zn1—O11.982 (3)C10—H10A0.9600
Zn1—N12.048 (3)C10—H10B0.9600
O1—C21.341 (5)C10—H10C0.9600
O2—C121.340 (5)C11—C161.407 (5)
O2—H20.8200C11—C121.419 (5)
O3—C211.343 (6)C12—C131.375 (6)
O3—H30.8200C13—C141.400 (6)
N1—C91.331 (5)C13—H130.9300
N1—C11.371 (5)C14—C151.369 (6)
N2—C191.333 (5)C14—H140.9300
N2—C111.373 (5)C15—C161.402 (6)
N2—H2N0.8600C15—H150.9300
C1—C61.412 (5)C16—C171.420 (6)
C1—C21.425 (6)C17—C181.359 (7)
C2—C31.385 (6)C17—H170.9300
C3—C41.402 (7)C18—C191.403 (6)
C3—H3a0.9300C18—H180.9300
C4—C51.359 (7)C19—C201.502 (7)
C4—H40.9300C20—H20A0.9600
C5—C61.409 (7)C20—H20B0.9600
C5—H50.9300C20—H20C0.9600
C6—C71.412 (6)C21—H21A0.9600
C7—C81.354 (7)C21—H21B0.9600
C7—H70.9300C21—H21C0.9600
C8—C91.410 (6)
O1—Zn1—N183.61 (12)H10A—C10—H10B109.5
O1—Zn1—I2112.82 (10)C9—C10—H10C109.5
N1—Zn1—I2111.95 (9)H10A—C10—H10C109.5
O1—Zn1—I1112.11 (10)H10B—C10—H10C109.5
N1—Zn1—I1120.50 (9)N2—C11—C16119.6 (4)
I2—Zn1—I1112.65 (2)N2—C11—C12119.6 (3)
C2—O1—Zn1111.6 (2)C16—C11—C12120.8 (4)
C12—O2—H2109.5O2—C12—C13126.1 (4)
C21—O3—H3109.5O2—C12—C11115.6 (4)
C9—N1—C1120.2 (3)C13—C12—C11118.3 (4)
C9—N1—Zn1130.5 (3)C12—C13—C14120.4 (4)
C1—N1—Zn1109.2 (2)C12—C13—H13119.8
C19—N2—C11123.4 (4)C14—C13—H13119.8
C19—N2—H2N118.3C15—C14—C13122.0 (4)
C11—N2—H2N118.3C15—C14—H14119.0
N1—C1—C6122.1 (4)C13—C14—H14119.0
N1—C1—C2117.1 (3)C14—C15—C16119.1 (4)
C6—C1—C2120.9 (4)C14—C15—H15120.5
O1—C2—C3123.7 (4)C16—C15—H15120.5
O1—C2—C1118.4 (4)C15—C16—C11119.3 (4)
C3—C2—C1117.9 (4)C15—C16—C17123.7 (4)
C2—C3—C4120.5 (4)C11—C16—C17117.0 (4)
C2—C3—H3a119.8C18—C17—C16121.0 (4)
C4—C3—H3a119.8C18—C17—H17119.5
C5—C4—C3122.2 (5)C16—C17—H17119.5
C5—C4—H4118.9C17—C18—C19120.5 (4)
C3—C4—H4118.9C17—C18—H18119.7
C4—C5—C6119.4 (4)C19—C18—H18119.7
C4—C5—H5120.3N2—C19—C18118.5 (4)
C6—C5—H5120.3N2—C19—C20118.8 (4)
C7—C6—C5124.7 (4)C18—C19—C20122.6 (4)
C7—C6—C1116.1 (4)C19—C20—H20A109.5
C5—C6—C1119.1 (4)C19—C20—H20B109.5
C8—C7—C6121.0 (4)H20A—C20—H20B109.5
C8—C7—H7119.5C19—C20—H20C109.5
C6—C7—H7119.5H20A—C20—H20C109.5
C7—C8—C9120.2 (4)H20B—C20—H20C109.5
C7—C8—H8119.9O3—C21—H21A109.5
C9—C8—H8119.9O3—C21—H21B109.5
N1—C9—C8120.3 (4)H21A—C21—H21B109.5
N1—C9—C10117.8 (4)O3—C21—H21C109.5
C8—C9—C10121.9 (4)H21A—C21—H21C109.5
C9—C10—H10A109.5H21B—C21—H21C109.5
C9—C10—H10B109.5
N1—Zn1—O1—C23.3 (3)C6—C7—C8—C90.6 (7)
I2—Zn1—O1—C2107.9 (3)C1—N1—C9—C80.8 (6)
I1—Zn1—O1—C2123.7 (3)Zn1—N1—C9—C8176.2 (3)
O1—Zn1—N1—C9178.9 (4)C1—N1—C9—C10178.8 (4)
I2—Zn1—N1—C966.8 (4)Zn1—N1—C9—C103.4 (6)
I1—Zn1—N1—C969.2 (4)C7—C8—C9—N10.3 (6)
O1—Zn1—N1—C13.1 (3)C7—C8—C9—C10179.3 (4)
I2—Zn1—N1—C1109.0 (2)C19—N2—C11—C160.3 (6)
I1—Zn1—N1—C1115.0 (2)C19—N2—C11—C12178.1 (4)
C9—N1—C1—C60.4 (6)N2—C11—C12—O20.6 (5)
Zn1—N1—C1—C6176.7 (3)C16—C11—C12—O2179.0 (4)
C9—N1—C1—C2178.7 (4)N2—C11—C12—C13179.4 (4)
Zn1—N1—C1—C22.4 (4)C16—C11—C12—C131.0 (6)
Zn1—O1—C2—C3175.7 (4)O2—C12—C13—C14179.1 (4)
Zn1—O1—C2—C12.9 (5)C11—C12—C13—C140.9 (6)
N1—C1—C2—O10.3 (6)C12—C13—C14—C150.7 (7)
C6—C1—C2—O1179.4 (4)C13—C14—C15—C160.6 (7)
N1—C1—C2—C3178.4 (4)C14—C15—C16—C110.7 (6)
C6—C1—C2—C30.7 (6)C14—C15—C16—C17178.4 (4)
O1—C2—C3—C4179.9 (4)N2—C11—C16—C15179.3 (4)
C1—C2—C3—C41.3 (7)C12—C11—C16—C150.9 (6)
C2—C3—C4—C50.7 (8)N2—C11—C16—C170.2 (6)
C3—C4—C5—C60.6 (8)C12—C11—C16—C17178.2 (4)
C4—C5—C6—C7178.9 (5)C15—C16—C17—C18179.1 (4)
C4—C5—C6—C11.1 (7)C11—C16—C17—C180.0 (6)
N1—C1—C6—C70.5 (6)C16—C17—C18—C190.1 (7)
C2—C1—C6—C7179.6 (4)C11—N2—C19—C180.2 (6)
N1—C1—C6—C5179.6 (4)C11—N2—C19—C20178.1 (4)
C2—C1—C6—C50.5 (6)C17—C18—C19—N20.0 (7)
C5—C6—C7—C8179.1 (4)C17—C18—C19—C20178.2 (5)
C1—C6—C7—C81.0 (6)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2···O10.821.742.559 (4)172
O3—H3···I1i0.822.883.575 (4)144
N2—H2n···O30.861.922.757 (5)165
Symmetry code: (i) x1, y, z.

Experimental details

Crystal data
Chemical formula(C10H10NO)[Zn(C10H8NO)I2]·CH4O
Mr669.58
Crystal system, space groupMonoclinic, P21/n
Temperature (K)295
a, b, c (Å)10.1745 (6), 14.6292 (9), 16.5321 (10)
β (°) 106.356 (1)
V3)2361.1 (2)
Z4
Radiation typeMo Kα
µ (mm1)3.68
Crystal size (mm)0.35 × 0.25 × 0.15
Data collection
DiffractometerBruker SMART APEX
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.359, 0.608
No. of measured, independent and
observed [I > 2σ(I)] reflections
21863, 5404, 4049
Rint0.031
(sin θ/λ)max1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.031, 0.090, 1.06
No. of reflections5404
No. of parameters267
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.73, 0.78

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···O10.821.742.559 (4)172
O3—H3···I1i0.822.883.575 (4)144
N2—H2n···O30.861.922.757 (5)165
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 citationSattarzadeh, E., Mohammadnezhad, G., Amini, M. M. & Ng, S. W. (2009). Acta Cryst. E65, m553.  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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