2-[(Z)-(3-{[(Z)-2-Hy­droxy-3,5-diiodo­benzyl­idene]amino}­propyl­imino)­meth­yl]-4,6-diiodo­phenol

Kargar, H.; Kia, R.; Adabi Ardakani, A.; Tahir, M.N.

doi:10.1107/S160053681203214X

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 8| August 2012| Page o2500

https://doi.org/10.1107/S160053681203214X

Open

access

2-[(Z)-(3-{[(Z)-2-Hydroxy-3,5-diiodobenzylidene]amino}propylimino)methyl]-4,6-diiodophenol

Hadi Kargar,^a Reza Kia,^b ^*‡ Amir Adabi Ardakani ^c and Muhammad Nawaz Tahir ^d ^*

^aDepartment of Chemistry, Payame Noor University, PO Box 19395-3697 Tehran, I. R. of IRAN, ^bDepartment of Chemistry, Science and Research Branch, Islamic Azad University, Tehran, Iran, ^cArdakan Branch, Islamic Azad University, Ardakan, Iran, and ^dDepartment of Physics, University of Sargodha, Punjab, Pakistan
^*Correspondence e-mail: zsrkk@yahoo.com, dmntahir_uos@yahoo.com

(Received 29 June 2012; accepted 14 July 2012; online 18 July 2012)

In the title compound, C₁₇H₁₄I₄N₂O₂, there are two intramolecular O—H⋯N hydrogen bonds, which make S(6) ring motifs. In the crystal, there are no significant intermolecular interactions present.

Related literature

For standard bond lengths, see: Allen et al. (1987 ). For hydrogen-bond motifs, see: Bernstein et al. (1995 ). For background to Schiff base ligands, see, for example: Kargar et al. (2011 ); Kia et al. (2010 ). For a related structure, see: Kargar et al. (2012 ).

Experimental

Crystal data

C₁₇H₁₄I₄N₂O₂
M_r = 785.90
Monoclinic, P 2₁ /n
a = 4.5578 (3) Å
b = 16.5095 (11) Å
c = 27.2417 (18) Å
β = 91.736 (4)°
V = 2048.9 (2) Å³
Z = 4
Mo Kα radiation
μ = 6.10 mm⁻¹
T = 291 K
0.30 × 0.14 × 0.14 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.262, T_max = 0.482
16049 measured reflections
4458 independent reflections
2832 reflections with I > 2σ(I)
R_int = 0.047

Refinement

R[F² > 2σ(F²)] = 0.035
wR(F²) = 0.059
S = 0.98
4458 reflections
226 parameters
H-atom parameters constrained
Δρ_max = 0.61 e Å⁻³
Δρ_min = −0.72 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.90	1.76	2.569 (5)	148
O2—H2⋯N2	0.89	1.75	2.564 (5)	150

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S160053681203214X/su2471sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S160053681203214X/su2471Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S160053681203214X/su2471Isup3.cml

checkCIF report

Comment top

In continuation of our work on the crystal structures of Schiff base ligands (Kargar et al., 2011; Kia et al., 2010), we synthesizes and carried out the X-ray structure analysis of the title compound.

In the title compound, Fig. 1, a potential tetradentate Schiff base ligand, there are two intramolecular O—H···N hydrogen bonds (Table 1) that make S(6) ring motifs (Bernstein et al., 1995). The bond lengths (Allen et al., 1987) and angles are within the normal ranges and are comparable to those reported for a similar structure (Kargar et al., 2012).

In the crystal, there are no significant intermolecular interactions present.

Related literature top

For standard bond lengths, see: Allen et al. (1987). For hydrogen-bond motifs, see: Bernstein et al. (1995). For background to Schiff base ligands, see, for example: Kargar et al. (2011); Kia et al. (2010). For a related structure, see: Kargar et al. (2012).

Experimental top

The title compound was synthesized by adding 3,5-dibromosalicylaldehyde (2 mmol) to a solution of propylenediamine (1 mmol) in ethanol (30 ml). The mixture was refluxed with stirring for 30 min. The resultant solution was filtered. Light-yellow prismatic single crystals of the title compound, suitable for X-ray structure determination, were obtained by recrystallization from ethanol by slow evaporation of the solvents at room temperature over several days.

Structure description top

In the crystal, there are no significant intermolecular interactions present.

For standard bond lengths, see: Allen et al. (1987). For hydrogen-bond motifs, see: Bernstein et al. (1995). For background to Schiff base ligands, see, for example: Kargar et al. (2011); Kia et al. (2010). For a related structure, see: Kargar et al. (2012).

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

Fig. 1. The molecular structure of the title compound, showing 40% probability displacement ellipsoids and the atomic numbering.

2-[(Z)-(3-{[(Z)-2-Hydroxy-3,5- diiodobenzylidene]amino}propylimino)methyl]-4,6-diiodophenol top

Crystal data top

C₁₇H₁₄I₄N₂O₂	F(000) = 1432
M_r = 785.90	D_x = 2.548 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2453 reflections
a = 4.5578 (3) Å	θ = 2.5–27.5°
b = 16.5095 (11) Å	µ = 6.10 mm⁻¹
c = 27.2417 (18) Å	T = 291 K
β = 91.736 (4)°	Needle, light-yellow
V = 2048.9 (2) Å³	0.30 × 0.14 × 0.14 mm
Z = 4

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	4458 independent reflections
Radiation source: fine-focus sealed tube	2832 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.047
φ and ω scans	θ_max = 27.1°, θ_min = 1.4°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −5→5
T_min = 0.262, T_max = 0.482	k = −21→17
16049 measured reflections	l = −34→34

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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.059	H-atom parameters constrained
S = 0.98	w = 1/[σ²(F_o²) + (0.0161P)²] where P = (F_o² + 2F_c²)/3
4458 reflections	(Δ/σ)_max = 0.002
226 parameters	Δρ_max = 0.61 e Å⁻³
0 restraints	Δρ_min = −0.71 e Å⁻³

Crystal data top

C₁₇H₁₄I₄N₂O₂	V = 2048.9 (2) Å³
M_r = 785.90	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 4.5578 (3) Å	µ = 6.10 mm⁻¹
b = 16.5095 (11) Å	T = 291 K
c = 27.2417 (18) Å	0.30 × 0.14 × 0.14 mm
β = 91.736 (4)°

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	4458 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	2832 reflections with I > 2σ(I)
T_min = 0.262, T_max = 0.482	R_int = 0.047
16049 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.035	0 restraints
wR(F²) = 0.059	H-atom parameters constrained
S = 0.98	Δρ_max = 0.61 e Å⁻³
4458 reflections	Δρ_min = −0.71 e Å⁻³
226 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
I1	−0.84612 (9)	1.18172 (2)	0.147565 (15)	0.05342 (13)
I2	−0.80900 (9)	0.88529 (2)	0.274765 (14)	0.05293 (13)
I3	0.66705 (10)	0.36716 (2)	0.091322 (16)	0.06029 (14)
I4	0.86332 (9)	0.67131 (2)	0.208721 (14)	0.05504 (13)
O1	−0.4461 (7)	1.0651 (2)	0.08517 (12)	0.0406 (9)
H1	−0.3177	1.0345	0.0688	0.061*
O2	0.4376 (7)	0.7341 (2)	0.12415 (12)	0.0446 (9)
H2	0.2946	0.7497	0.1030	0.067*
N1	−0.1123 (8)	0.9443 (2)	0.06648 (15)	0.0350 (10)
N2	0.0681 (9)	0.7303 (3)	0.05131 (15)	0.0395 (11)
C1	−0.5088 (10)	1.0271 (3)	0.12709 (18)	0.0303 (12)
C2	−0.6977 (10)	1.0640 (3)	0.16025 (19)	0.0322 (12)
C3	−0.7811 (11)	1.0236 (3)	0.20139 (19)	0.0377 (13)
H3	−0.9105	1.0480	0.2226	0.045*
C4	−0.6736 (11)	0.9465 (3)	0.21164 (17)	0.0341 (13)
C5	−0.4784 (10)	0.9102 (3)	0.18129 (18)	0.0329 (12)
H5	−0.4028	0.8593	0.1890	0.040*
C6	−0.3933 (10)	0.9501 (3)	0.13875 (18)	0.0294 (12)
C7	−0.1787 (10)	0.9141 (3)	0.10729 (18)	0.0342 (13)
H7	−0.0857	0.8666	0.1175	0.041*
C8	0.1172 (11)	0.9065 (3)	0.03753 (18)	0.0378 (13)
H8A	0.2494	0.8767	0.0594	0.045*
H8B	0.2299	0.9487	0.0220	0.045*
C9	−0.0043 (11)	0.8493 (3)	−0.00185 (18)	0.0391 (14)
H9A	0.1530	0.8340	−0.0232	0.047*
H9B	−0.1519	0.8776	−0.0217	0.047*
C10	−0.1411 (11)	0.7724 (3)	0.01916 (18)	0.0415 (14)
H10A	−0.3131	0.7867	0.0374	0.050*
H10B	−0.2030	0.7368	−0.0075	0.050*
C11	0.1244 (10)	0.6563 (3)	0.04552 (19)	0.0375 (13)
H11	0.0295	0.6283	0.0200	0.045*
C12	0.3351 (10)	0.6128 (3)	0.07772 (19)	0.0351 (13)
C13	0.3936 (11)	0.5311 (3)	0.07004 (19)	0.0407 (14)
H13	0.3015	0.5036	0.0441	0.049*
C14	0.5879 (11)	0.4914 (3)	0.1010 (2)	0.0387 (13)
C15	0.7236 (11)	0.5313 (3)	0.14057 (19)	0.0381 (13)
H15	0.8510	0.5032	0.1618	0.046*
C16	0.6701 (11)	0.6115 (3)	0.14830 (18)	0.0352 (13)
C17	0.4795 (11)	0.6551 (3)	0.11703 (19)	0.0347 (13)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
I1	0.0713 (3)	0.0303 (2)	0.0585 (3)	0.0101 (2)	−0.0011 (2)	−0.0040 (2)
I2	0.0675 (3)	0.0569 (3)	0.0348 (2)	−0.0083 (2)	0.00783 (19)	0.0078 (2)
I3	0.0820 (3)	0.0365 (2)	0.0627 (3)	0.0121 (2)	0.0063 (2)	−0.0041 (2)
I4	0.0633 (3)	0.0545 (3)	0.0467 (2)	−0.0014 (2)	−0.0092 (2)	−0.0021 (2)
O1	0.051 (2)	0.033 (2)	0.038 (2)	0.0030 (17)	0.0072 (18)	0.0107 (18)
O2	0.057 (2)	0.031 (2)	0.046 (2)	0.0008 (18)	−0.0050 (19)	0.0028 (19)
N1	0.034 (3)	0.037 (3)	0.034 (3)	−0.001 (2)	0.004 (2)	0.003 (2)
N2	0.042 (3)	0.038 (3)	0.039 (3)	0.001 (2)	0.001 (2)	0.002 (2)
C1	0.034 (3)	0.023 (3)	0.033 (3)	−0.010 (2)	−0.004 (3)	0.001 (3)
C2	0.036 (3)	0.019 (3)	0.042 (3)	0.001 (2)	−0.003 (3)	−0.004 (3)
C3	0.044 (3)	0.032 (3)	0.038 (3)	−0.001 (3)	0.006 (3)	−0.010 (3)
C4	0.041 (3)	0.033 (3)	0.028 (3)	−0.006 (3)	0.001 (3)	−0.002 (3)
C5	0.038 (3)	0.031 (3)	0.029 (3)	0.001 (2)	−0.008 (3)	0.002 (3)
C6	0.032 (3)	0.023 (3)	0.032 (3)	−0.001 (2)	−0.007 (2)	−0.002 (2)
C7	0.035 (3)	0.031 (3)	0.037 (3)	0.005 (2)	−0.004 (3)	−0.001 (3)
C8	0.037 (3)	0.042 (3)	0.035 (3)	0.002 (3)	0.007 (3)	0.002 (3)
C9	0.041 (3)	0.046 (4)	0.031 (3)	0.011 (3)	0.001 (3)	0.001 (3)
C10	0.038 (3)	0.046 (4)	0.039 (3)	0.004 (3)	−0.007 (3)	−0.005 (3)
C11	0.034 (3)	0.044 (4)	0.035 (3)	−0.001 (3)	0.004 (3)	0.000 (3)
C12	0.033 (3)	0.036 (3)	0.037 (3)	−0.001 (3)	0.007 (3)	0.007 (3)
C13	0.046 (4)	0.039 (3)	0.038 (3)	−0.002 (3)	0.010 (3)	−0.005 (3)
C14	0.041 (3)	0.026 (3)	0.049 (4)	0.004 (2)	0.011 (3)	−0.003 (3)
C15	0.043 (3)	0.037 (3)	0.035 (3)	0.004 (3)	0.005 (3)	0.003 (3)
C16	0.038 (3)	0.031 (3)	0.037 (3)	−0.002 (3)	0.003 (3)	0.006 (3)
C17	0.039 (3)	0.030 (3)	0.035 (3)	−0.004 (3)	0.014 (3)	0.000 (3)

Geometric parameters (Å, º) top

I1—C2	2.083 (5)	C6—C7	1.447 (6)
I2—C4	2.103 (5)	C7—H7	0.9300
I3—C14	2.100 (5)	C8—C9	1.521 (6)
I4—C16	2.091 (5)	C8—H8A	0.9700
O1—C1	1.341 (5)	C8—H8B	0.9700
O1—H1	0.9004	C9—C10	1.533 (6)
O2—C17	1.334 (5)	C9—H9A	0.9700
O2—H2	0.8944	C9—H9B	0.9700
N1—C7	1.264 (6)	C10—H10A	0.9700
N1—C8	1.468 (6)	C10—H10B	0.9700
N2—C11	1.260 (6)	C11—C12	1.468 (7)
N2—C10	1.452 (6)	C11—H11	0.9300
C1—C2	1.405 (6)	C12—C13	1.392 (6)
C1—C6	1.409 (6)	C12—C17	1.422 (7)
C2—C3	1.367 (6)	C13—C14	1.372 (7)
C3—C4	1.390 (7)	C13—H13	0.9300
C3—H3	0.9300	C14—C15	1.392 (7)
C4—C5	1.370 (6)	C15—C16	1.364 (6)
C5—C6	1.397 (6)	C15—H15	0.9300
C5—H5	0.9300	C16—C17	1.397 (7)

C1—O1—H1	108.6	C8—C9—H9A	108.9
C17—O2—H2	107.0	C10—C9—H9A	108.9
C7—N1—C8	119.9 (4)	C8—C9—H9B	108.9
C11—N2—C10	121.4 (4)	C10—C9—H9B	108.9
O1—C1—C2	119.7 (4)	H9A—C9—H9B	107.7
O1—C1—C6	121.7 (5)	N2—C10—C9	110.7 (4)
C2—C1—C6	118.5 (5)	N2—C10—H10A	109.5
C3—C2—C1	120.4 (4)	C9—C10—H10A	109.5
C3—C2—I1	119.6 (4)	N2—C10—H10B	109.5
C1—C2—I1	120.0 (4)	C9—C10—H10B	109.5
C2—C3—C4	120.4 (5)	H10A—C10—H10B	108.1
C2—C3—H3	119.8	N2—C11—C12	122.1 (5)
C4—C3—H3	119.8	N2—C11—H11	118.9
C5—C4—C3	120.7 (5)	C12—C11—H11	118.9
C5—C4—I2	119.7 (4)	C13—C12—C17	120.1 (5)
C3—C4—I2	119.6 (4)	C13—C12—C11	120.6 (5)
C4—C5—C6	119.8 (5)	C17—C12—C11	119.3 (5)
C4—C5—H5	120.1	C14—C13—C12	119.6 (5)
C6—C5—H5	120.1	C14—C13—H13	120.2
C5—C6—C1	120.0 (5)	C12—C13—H13	120.2
C5—C6—C7	120.5 (4)	C13—C14—C15	120.9 (5)
C1—C6—C7	119.4 (5)	C13—C14—I3	120.0 (4)
N1—C7—C6	122.9 (5)	C15—C14—I3	119.1 (4)
N1—C7—H7	118.6	C16—C15—C14	120.1 (5)
C6—C7—H7	118.6	C16—C15—H15	119.9
N1—C8—C9	113.1 (4)	C14—C15—H15	119.9
N1—C8—H8A	109.0	C15—C16—C17	121.1 (5)
C9—C8—H8A	109.0	C15—C16—I4	120.5 (4)
N1—C8—H8B	109.0	C17—C16—I4	118.4 (4)
C9—C8—H8B	109.0	O2—C17—C16	120.3 (5)
H8A—C8—H8B	107.8	O2—C17—C12	121.6 (5)
C8—C9—C10	113.3 (4)	C16—C17—C12	118.1 (5)

O1—C1—C2—C3	175.1 (4)	C11—N2—C10—C9	−127.5 (5)
C6—C1—C2—C3	−3.9 (7)	C8—C9—C10—N2	−55.5 (6)
O1—C1—C2—I1	−6.0 (6)	C10—N2—C11—C12	−179.9 (4)
C6—C1—C2—I1	174.9 (3)	N2—C11—C12—C13	−179.5 (5)
C1—C2—C3—C4	1.8 (7)	N2—C11—C12—C17	0.5 (8)
I1—C2—C3—C4	−177.0 (4)	C17—C12—C13—C14	0.9 (8)
C2—C3—C4—C5	1.2 (7)	C11—C12—C13—C14	−179.0 (5)
C2—C3—C4—I2	−179.4 (3)	C12—C13—C14—C15	1.1 (8)
C3—C4—C5—C6	−2.0 (7)	C12—C13—C14—I3	177.9 (4)
I2—C4—C5—C6	178.6 (3)	C13—C14—C15—C16	−1.6 (8)
C4—C5—C6—C1	−0.2 (7)	I3—C14—C15—C16	−178.4 (4)
C4—C5—C6—C7	177.6 (4)	C14—C15—C16—C17	0.0 (8)
O1—C1—C6—C5	−175.9 (4)	C14—C15—C16—I4	178.2 (4)
C2—C1—C6—C5	3.1 (7)	C15—C16—C17—O2	−177.7 (5)
O1—C1—C6—C7	6.3 (7)	I4—C16—C17—O2	4.1 (6)
C2—C1—C6—C7	−174.7 (4)	C15—C16—C17—C12	2.0 (7)
C8—N1—C7—C6	177.2 (4)	I4—C16—C17—C12	−176.3 (3)
C5—C6—C7—N1	174.0 (4)	C13—C12—C17—O2	177.2 (5)
C1—C6—C7—N1	−8.2 (7)	C11—C12—C17—O2	−2.9 (7)
C7—N1—C8—C9	96.3 (5)	C13—C12—C17—C16	−2.5 (7)
N1—C8—C9—C10	−68.6 (5)	C11—C12—C17—C16	177.5 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.90	1.76	2.569 (5)	148
O2—H2···N2	0.89	1.75	2.564 (5)	150

Experimental details

Crystal data
Chemical formula	C₁₇H₁₄I₄N₂O₂
M_r	785.90
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	291
a, b, c (Å)	4.5578 (3), 16.5095 (11), 27.2417 (18)
β (°)	91.736 (4)
V (Å³)	2048.9 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	6.10
Crystal size (mm)	0.30 × 0.14 × 0.14

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.262, 0.482
No. of measured, independent and observed [I > 2σ(I)] reflections	16049, 4458, 2832
R_int	0.047
(sin θ/λ)_max (Å⁻¹)	0.641

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.035, 0.059, 0.98
No. of reflections	4458
No. of parameters	226
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.61, −0.71

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.90	1.76	2.569 (5)	148
O2—H2···N2	0.89	1.75	2.564 (5)	150

Footnotes

‡Present address: Structural Dynamics of (Bio)Chemical Systems, Max Planck Institute for Biophysical Chemistry, Am Fassberg 11, 37077 Göttingen, Germany.

Acknowledgements

HK and AAA thank PNU for financial support. MNT thanks the GC University of Sargodha, Pakistan, for the research facility.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CSD CrossRef Web of Science Google Scholar
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573. CrossRef CAS Web of Science Google Scholar
Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Kargar, H., Kia, R., Adabi Ardakani, A. & Tahir, M. N. (2012). Acta Cryst. E68, o2323. CSD CrossRef IUCr Journals Google Scholar
Kargar, H., Kia, R., Pahlavani, E. & Tahir, M. N. (2011). Acta Cryst. E67, o614. Web of Science CSD CrossRef IUCr Journals Google Scholar
Kia, R., Kargar, H., Tahir, M. N. & Kianoosh, F. (2010). Acta Cryst. E66, o2296. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. 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.