(E)-N-(2,4-Dimeth­oxy­benzyl­idene)-4-ethoxyaniline

Fejfarová, K.; Khalaji, A.D.; Dušek, M.

doi:10.1107/S1600536810041759

organic compounds

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ISSN: 2056-9890

Volume 66| Part 11| November 2010| Page o2874

https://doi.org/10.1107/S1600536810041759

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(E)-N-(2,4-Dimethoxybenzylidene)-4-ethoxyaniline

Karla Fejfarová,^a ^* Aliakbar Dehno Khalaji ^b and Michal Dušek ^c

^aInstitute of Physics of the ASCR, v.v.i., Na Slovance 2, 182 21 Praha 8, Czech Republic, ^bDepartment of Chemistry, Faculty of Science, Golestan University, Gorgan, Iran, and ^cInstitute of Physics, Na Slovance 2, 182 21 Praha 8, Czech Republic
^*Correspondence e-mail: fejfarov@fzu.cz

(Received 14 October 2010; accepted 15 October 2010; online 20 October 2010)

In the title compound, C₁₇H₁₉NO₃, the molecule has an E configuration with respect to the C=N bond and the dihedral angle between the aromatic rings is 56.07 (5)°. In the crystal, inversion dimers linked by pairs of C—H⋯O hydrogen bonds occur. The dimers are linked by weak C—H⋯π interactions, forming a three-dimensional network.

Related literature

For related structures and background references, see: Khalaji et al. (2010a ,b ).

Experimental

Crystal data

C₁₇H₁₉NO₃
M_r = 285.3
Monoclinic, P 2₁ /c
a = 8.4536 (1) Å
b = 9.6531 (2) Å
c = 18.0561 (3) Å
β = 90.9091 (10)°
V = 1473.25 (4) Å³
Z = 4
Cu Kα radiation
μ = 0.71 mm⁻¹
T = 120 K
0.50 × 0.12 × 0.11 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with Atlas (Gemini ultra Cu) detector
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis PRO, Oxford Diffraction Ltd., Oxford, UK.]$ ), T_min = 0.714, T_max = 1.000
18522 measured reflections
2543 independent reflections
2259 reflections with I > 3σ(I)
R_int = 0.024

Refinement

R[F² > 2σ(F²)] = 0.030
wR(F²) = 0.098
S = 1.98
2543 reflections
190 parameters
H-atom parameters constrained
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.13 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C1–C6 and C10–C15 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8c⋯O2ⁱ	0.96	2.52	3.3745 (13)	148
C5—H5⋯Cg2ⁱⁱ	0.96	2.88	3.7529 (11)	152
C14—H14⋯Cg1ⁱⁱⁱ	0.96	2.76	3.6019 (11)	147
Symmetry codes: (i) -x+2, -y, -z+2; (ii) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (iii) $[-x+1, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis PRO, Oxford Diffraction Ltd., Oxford, UK.]$ ); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SIR2002 (Burla et al., 2003 ); program(s) used to refine structure: JANA2006 (Petříček et al., 2007 ); molecular graphics: DIAMOND (Brandenburg & Putz, 2005 ); software used to prepare material for publication: JANA2006.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536810041759/hb5685sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810041759/hb5685Isup2.hkl

checkCIF report

Comment top

As part of our ongoing studies of Schiff bases (Khalaji et al., 2010a and 2010b) we now report the synthesis and crystal structure of the title compound, (I).

The title molecule with the atomic numbering scheme is depicted in Fig. 1. The C7—N1 and C10—N1 bond lengths of 1.2795 (13), 1.4171 (13) Å, respectively, conform to the value for a double and single bonds, respectively, and they are similar to the corresponding bond lengths in another Schiff-base compounds (Khalaji et al., 2010a and 2010b).

The torsion angle of the title compound, C10—N1—C7—C1 - 175.18 (9)°, indicates virtually planar E-configuration with respect to the imine C–N bond. Both methoxy groups are nearly coplanar with the C1—C6 ring, as indicated by torsion angles C3—C4—O2—C9 and C1—C2—O1—C8 of 178.16 (9)°, -175.74 (9)°, respectively. The ethoxy group is nearly coplanar with the C10—C15 ring, with the dihedral angle between the ring plane and plane defined by atoms O3, C16 and C17 of 6.28 (9)°.

In the crystal, molecules are connected by weak C—H···O interactions into dimers, which are further linked by C—H···π interactions into a three-dimensional network.

Related literature top

For related structures and background references, see: Khalaji et al. (2010a,b).

Structure description top

As part of our ongoing studies of Schiff bases (Khalaji et al., 2010a and 2010b) we now report the synthesis and crystal structure of the title compound, (I).

In the crystal, molecules are connected by weak C—H···O interactions into dimers, which are further linked by C—H···π interactions into a three-dimensional network.

For related structures and background references, see: Khalaji et al. (2010a,b).

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2009); cell refinement: CrysAlis PRO (Oxford Diffraction, 2009); data reduction: CrysAlis PRO (Oxford Diffraction, 2009); program(s) used to solve structure: SIR2002 (Burla et al., 2003); program(s) used to refine structure: JANA2006 (Petříček et al., 2007); molecular graphics: DIAMOND (Brandenburg & Putz, 2005); software used to prepare material for publication: JANA2006 (Petříček et al., 2007).

Figures top

	Fig. 1. View of (I) with displacement ellipsoids drawn at the 50% probability level. C—H···O bonds are drawn as blue dashed lines. [Symmetry codes: (i) 2 - x, -y, 2 - z]
	Fig. 2. Crystal packing of (I) viewed along the a axis. Hydrogen bonds are displayed as blue dashed lines, C—H···π interactions as red dashed lines.

(E)-N-(2,4-Dimethoxybenzylidene)-4-ethoxyaniline top

Crystal data top

C₁₇H₁₉NO₃	F(000) = 608
M_r = 285.3	D_x = 1.286 Mg m⁻³
Monoclinic, P2₁/c	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: -P 2ybc	Cell parameters from 13339 reflections
a = 8.4536 (1) Å	θ = 4.6–66.4°
b = 9.6531 (2) Å	µ = 0.71 mm⁻¹
c = 18.0561 (3) Å	T = 120 K
β = 90.9091 (10)°	Prism, colourless
V = 1473.25 (4) Å³	0.50 × 0.12 × 0.11 mm
Z = 4

Data collection top

Oxford Diffraction Xcalibur diffractometer with Atlas (Gemini ultra Cu) detector	2543 independent reflections
Radiation source: X-ray tube	2259 reflections with I > 3σ(I)
Mirror monochromator	R_int = 0.024
Detector resolution: 10.3784 pixels mm^-1	θ_max = 66.6°, θ_min = 4.9°
Rotation method data acquisition using ω scans	h = −9→9
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009),	k = −11→11
T_min = 0.714, T_max = 1.000	l = −21→21
18522 measured reflections

Refinement top

Refinement on F²	76 constraints
R[F > 3σ(F)] = 0.030	H-atom parameters constrained
wR(F) = 0.098	Weighting scheme based on measured s.u.'s w = 1/(σ²(I) + 0.0016I²)
S = 1.98	(Δ/σ)_max = 0.013
2543 reflections	Δρ_max = 0.17 e Å⁻³
190 parameters	Δρ_min = −0.13 e Å⁻³
0 restraints

Crystal data top

C₁₇H₁₉NO₃	V = 1473.25 (4) Å³
M_r = 285.3	Z = 4
Monoclinic, P2₁/c	Cu Kα radiation
a = 8.4536 (1) Å	µ = 0.71 mm⁻¹
b = 9.6531 (2) Å	T = 120 K
c = 18.0561 (3) Å	0.50 × 0.12 × 0.11 mm
β = 90.9091 (10)°

Data collection top

Oxford Diffraction Xcalibur diffractometer with Atlas (Gemini ultra Cu) detector	2543 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009),	2259 reflections with I > 3σ(I)
T_min = 0.714, T_max = 1.000	R_int = 0.024
18522 measured reflections

Refinement top

R[F > 3σ(F)] = 0.030	0 restraints
wR(F) = 0.098	H-atom parameters constrained
S = 1.98	Δρ_max = 0.17 e Å⁻³
2543 reflections	Δρ_min = −0.13 e Å⁻³
190 parameters

Special details top

Experimental. Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

Refinement. The refinement was carried out against all reflections. The conventional R-factor is always based on F. The goodness of fit as well as the weighted R-factor are based on F and F² for refinement carried out on F and F², respectively. The threshold expression is used only for calculating R-factors etc. and it is not relevant to the choice of reflections for refinement.

The program used for refinement, Jana2006, uses the weighting scheme based on the experimental expectations, see _refine_ls_weighting_details, that does not force S to be one. Therefore the values of S are usually larger than the ones from the SHELX program.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O1	0.84529 (8)	0.12294 (8)	0.81770 (4)	0.0248 (2)
O2	0.78640 (8)	0.15086 (8)	1.07814 (4)	0.0271 (2)
O3	0.16362 (8)	0.12599 (7)	0.48157 (4)	0.0244 (2)
N1	0.38690 (10)	0.18316 (9)	0.77253 (5)	0.0231 (3)
C1	0.59085 (11)	0.15330 (10)	0.86553 (6)	0.0206 (3)
C2	0.75506 (12)	0.13694 (10)	0.87911 (6)	0.0204 (3)
C3	0.81587 (11)	0.13725 (10)	0.95058 (6)	0.0220 (3)
C4	0.71412 (12)	0.15436 (10)	1.00995 (6)	0.0214 (3)
C5	0.55251 (12)	0.17397 (10)	0.99830 (6)	0.0229 (3)
C6	0.49391 (12)	0.17310 (10)	0.92638 (6)	0.0222 (3)
C7	0.52727 (11)	0.14440 (10)	0.79015 (6)	0.0207 (3)
C8	1.01066 (11)	0.09643 (12)	0.82857 (6)	0.0281 (3)
C9	0.68947 (13)	0.17194 (12)	1.14125 (6)	0.0284 (3)
C10	0.33285 (11)	0.16001 (11)	0.69888 (5)	0.0212 (3)
C11	0.23872 (11)	0.26224 (11)	0.66542 (6)	0.0243 (3)
C12	0.18457 (11)	0.24746 (11)	0.59337 (6)	0.0240 (3)
C13	0.22075 (11)	0.12870 (10)	0.55293 (5)	0.0210 (3)
C14	0.30901 (11)	0.02359 (11)	0.58635 (6)	0.0233 (3)
C15	0.36467 (11)	0.03995 (11)	0.65886 (6)	0.0229 (3)
C16	0.19378 (12)	0.00331 (11)	0.43883 (6)	0.0259 (3)
C17	0.13061 (13)	0.02869 (12)	0.36162 (6)	0.0309 (3)
H3	0.927413	0.125758	0.959322	0.0265*
H5	0.483291	0.187796	1.039282	0.0275*
H6	0.382532	0.186607	0.91805	0.0267*
H7	0.593525	0.107913	0.752123	0.0248*
H8a	1.059899	0.085896	0.781357	0.0337*
H8b	1.05849	0.172598	0.854758	0.0337*
H8c	1.024488	0.013012	0.856891	0.0337*
H9a	0.754648	0.173238	1.185267	0.0341*
H9b	0.634743	0.258688	1.136412	0.0341*
H9c	0.61388	0.098051	1.144473	0.0341*
H11	0.211463	0.343686	0.692928	0.0292*
H12	0.121631	0.319295	0.570909	0.0288*
H14	0.331465	−0.059847	0.559561	0.028*
H15	0.425927	−0.032629	0.681647	0.0274*
H16a	0.139336	−0.07389	0.4602	0.0311*
H16b	0.305721	−0.012837	0.437197	0.0311*
H17a	0.142647	−0.053732	0.332495	0.0371*
H17b	0.020596	0.052809	0.363673	0.0371*
H17c	0.188299	0.103188	0.339434	0.0371*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0173 (4)	0.0359 (4)	0.0213 (4)	0.0025 (3)	0.0015 (3)	−0.0005 (3)
O2	0.0258 (4)	0.0364 (5)	0.0190 (4)	0.0060 (3)	−0.0017 (3)	−0.0013 (3)
O3	0.0267 (4)	0.0261 (4)	0.0204 (4)	0.0031 (3)	−0.0028 (3)	−0.0019 (3)
N1	0.0203 (4)	0.0268 (5)	0.0222 (4)	0.0007 (3)	−0.0013 (3)	0.0002 (3)
C1	0.0193 (5)	0.0176 (5)	0.0248 (5)	−0.0007 (4)	−0.0006 (4)	0.0012 (4)
C2	0.0203 (5)	0.0180 (5)	0.0230 (5)	−0.0002 (4)	0.0021 (4)	0.0004 (4)
C3	0.0183 (5)	0.0225 (5)	0.0252 (6)	0.0013 (4)	−0.0018 (4)	−0.0005 (4)
C4	0.0249 (5)	0.0184 (5)	0.0208 (5)	0.0009 (4)	−0.0026 (4)	0.0001 (4)
C5	0.0233 (5)	0.0230 (5)	0.0226 (5)	0.0016 (4)	0.0038 (4)	0.0002 (4)
C6	0.0172 (5)	0.0224 (5)	0.0271 (5)	0.0009 (4)	−0.0003 (4)	0.0007 (4)
C7	0.0192 (5)	0.0200 (5)	0.0228 (5)	−0.0010 (4)	0.0025 (4)	0.0008 (4)
C8	0.0168 (5)	0.0392 (6)	0.0284 (5)	0.0011 (4)	0.0020 (4)	0.0011 (5)
C9	0.0338 (6)	0.0323 (6)	0.0193 (5)	0.0019 (5)	0.0022 (4)	−0.0003 (4)
C10	0.0155 (5)	0.0261 (5)	0.0222 (5)	−0.0015 (4)	0.0013 (4)	0.0005 (4)
C11	0.0212 (5)	0.0266 (6)	0.0252 (5)	0.0030 (4)	0.0009 (4)	−0.0028 (4)
C12	0.0207 (5)	0.0251 (6)	0.0262 (5)	0.0039 (4)	−0.0008 (4)	0.0010 (4)
C13	0.0174 (5)	0.0250 (5)	0.0206 (5)	−0.0023 (4)	0.0010 (4)	0.0012 (4)
C14	0.0222 (5)	0.0214 (5)	0.0264 (5)	−0.0006 (4)	−0.0002 (4)	−0.0022 (4)
C15	0.0194 (5)	0.0225 (5)	0.0266 (5)	0.0001 (4)	−0.0016 (4)	0.0031 (4)
C16	0.0257 (5)	0.0266 (6)	0.0256 (5)	0.0014 (4)	0.0001 (4)	−0.0040 (4)
C17	0.0347 (6)	0.0332 (6)	0.0248 (5)	0.0006 (5)	−0.0008 (4)	−0.0039 (4)

Geometric parameters (Å, º) top

O1—C2	1.3626 (12)	C8—H8c	0.96
O1—C8	1.4317 (11)	C9—H9a	0.96
O2—C4	1.3662 (12)	C9—H9b	0.96
O2—C9	1.4286 (13)	C9—H9c	0.96
O3—C13	1.3690 (12)	C10—C11	1.3988 (14)
O3—C16	1.4385 (13)	C10—C15	1.3942 (14)
N1—C7	1.2795 (13)	C11—C12	1.3797 (14)
N1—C10	1.4171 (13)	C11—H11	0.96
C1—C2	1.4147 (14)	C12—C13	1.3957 (14)
C1—C6	1.3943 (14)	C12—H12	0.96
C1—C7	1.4578 (14)	C13—C14	1.3915 (14)
C2—C3	1.3814 (14)	C14—C15	1.3932 (14)
C3—C4	1.3948 (14)	C14—H14	0.96
C3—H3	0.96	C15—H15	0.96
C4—C5	1.3919 (14)	C16—C17	1.5051 (15)
C5—C6	1.3824 (14)	C16—H16a	0.96
C5—H5	0.96	C16—H16b	0.96
C6—H6	0.96	C17—H17a	0.96
C7—H7	0.96	C17—H17b	0.96
C8—H8a	0.96	C17—H17c	0.96
C8—H8b	0.96

C2—O1—C8	117.65 (7)	H9a—C9—H9b	109.4721
C4—O2—C9	117.48 (8)	H9a—C9—H9c	109.4713
C13—O3—C16	117.24 (8)	H9b—C9—H9c	109.4713
C7—N1—C10	118.11 (8)	N1—C10—C11	117.83 (9)
C2—C1—C6	117.78 (9)	N1—C10—C15	123.74 (9)
C2—C1—C7	120.11 (9)	C11—C10—C15	118.41 (9)
C6—C1—C7	122.08 (9)	C10—C11—C12	120.81 (10)
O1—C2—C1	115.49 (8)	C10—C11—H11	119.5938
O1—C2—C3	123.75 (9)	C12—C11—H11	119.5935
C1—C2—C3	120.75 (9)	C11—C12—C13	120.40 (9)
C2—C3—C4	119.55 (9)	C11—C12—H12	119.798
C2—C3—H3	120.2241	C13—C12—H12	119.7978
C4—C3—H3	120.2224	O3—C13—C12	115.53 (9)
O2—C4—C3	114.66 (9)	O3—C13—C14	124.96 (9)
O2—C4—C5	124.29 (9)	C12—C13—C14	119.50 (9)
C3—C4—C5	121.05 (9)	C13—C14—C15	119.71 (9)
C4—C5—C6	118.51 (9)	C13—C14—H14	120.1429
C4—C5—H5	120.7434	C15—C14—H14	120.1429
C6—C5—H5	120.7439	C10—C15—C14	121.08 (9)
C1—C6—C5	122.32 (9)	C10—C15—H15	119.46
C1—C6—H6	118.8378	C14—C15—H15	119.4596
C5—C6—H6	118.8386	O3—C16—C17	107.44 (8)
N1—C7—C1	122.80 (9)	O3—C16—H16a	109.4712
N1—C7—H7	118.601	O3—C16—H16b	109.4719
C1—C7—H7	118.601	C17—C16—H16a	109.471
O1—C8—H8a	109.4708	C17—C16—H16b	109.4701
O1—C8—H8b	109.4712	H16a—C16—H16b	111.434
O1—C8—H8c	109.4709	C16—C17—H17a	109.4709
H8a—C8—H8b	109.4718	C16—C17—H17b	109.4708
H8a—C8—H8c	109.4713	C16—C17—H17c	109.4707
H8b—C8—H8c	109.4713	H17a—C17—H17b	109.4715
O2—C9—H9a	109.4707	H17a—C17—H17c	109.4719
O2—C9—H9b	109.4712	H17b—C17—H17c	109.4715
O2—C9—H9c	109.4708

C8—O1—C2—C1	−175.74 (9)	O1—C2—C3—C4	179.02 (9)
C8—O1—C2—C3	4.99 (14)	C1—C2—C3—C4	−0.22 (15)
C9—O2—C4—C3	178.16 (9)	C2—C3—C4—O2	179.02 (9)
C9—O2—C4—C5	−1.49 (14)	C2—C3—C4—C5	−1.32 (15)
C16—O3—C13—C12	−177.94 (8)	O2—C4—C5—C6	−178.96 (9)
C16—O3—C13—C14	1.80 (13)	C3—C4—C5—C6	1.42 (14)
C13—O3—C16—C17	−176.02 (8)	C4—C5—C6—C1	0.03 (16)
C10—N1—C7—C1	−175.18 (9)	N1—C10—C11—C12	178.79 (9)
C7—N1—C10—C11	−141.76 (10)	C15—C10—C11—C12	−2.88 (14)
C7—N1—C10—C15	40.01 (14)	N1—C10—C15—C14	−179.59 (9)
C6—C1—C2—O1	−177.72 (9)	C11—C10—C15—C14	2.20 (14)
C6—C1—C2—C3	1.57 (14)	C10—C11—C12—C13	1.09 (15)
C7—C1—C2—O1	4.41 (13)	C11—C12—C13—O3	−178.79 (9)
C7—C1—C2—C3	−176.30 (9)	C11—C12—C13—C14	1.45 (14)
C2—C1—C6—C5	−1.49 (15)	O3—C13—C14—C15	178.14 (9)
C7—C1—C6—C5	176.34 (9)	C12—C13—C14—C15	−2.12 (14)
C2—C1—C7—N1	−166.67 (10)	C13—C14—C15—C10	0.29 (15)
C6—C1—C7—N1	15.55 (15)

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of the C1–C6 and C10–C15 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8c···O2ⁱ	0.96	2.52	3.3745 (13)	148
C5—H5···Cg2ⁱⁱ	0.96	2.88	3.7529 (11)	152
C14—H14···Cg1ⁱⁱⁱ	0.96	2.76	3.6019 (11)	147

Symmetry codes: (i) −x+2, −y, −z+2; (ii) x, −y+1/2, z+1/2; (iii) −x+1, y−1/2, −z+3/2.

Experimental details

Crystal data
Chemical formula	C₁₇H₁₉NO₃
M_r	285.3
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	120
a, b, c (Å)	8.4536 (1), 9.6531 (2), 18.0561 (3)
β (°)	90.9091 (10)
V (Å³)	1473.25 (4)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	0.71
Crystal size (mm)	0.50 × 0.12 × 0.11

Data collection
Diffractometer	Oxford Diffraction Xcalibur diffractometer with Atlas (Gemini ultra Cu) detector
Absorption correction	Multi-scan (CrysAlis PRO; Oxford Diffraction, 2009),
T_min, T_max	0.714, 1.000
No. of measured, independent and observed [I > 3σ(I)] reflections	18522, 2543, 2259
R_int	0.024
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F > 3σ(F)], wR(F), S	0.030, 0.098, 1.98
No. of reflections	2543
No. of parameters	190
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.17, −0.13

Computer programs: CrysAlis PRO (Oxford Diffraction, 2009), SIR2002 (Burla et al., 2003), JANA2006 (Petříček et al., 2007), DIAMOND (Brandenburg & Putz, 2005).

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of the C1–C6 and C10–C15 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8c···O2ⁱ	0.96	2.52	3.3745 (13)	148
C5—H5···Cg2ⁱⁱ	0.96	2.88	3.7529 (11)	152
C14—H14···Cg1ⁱⁱⁱ	0.96	2.76	3.6019 (11)	147

Symmetry codes: (i) −x+2, −y, −z+2; (ii) x, −y+1/2, z+1/2; (iii) −x+1, y−1/2, −z+3/2.

Acknowledgements

We acknowledge Golestan University (GU), the Institutional research plan No. AVOZ10100521 of the Institute of Physics and the Praemium Academiae project of the Academy of Sciences of the Czech Republic.

References

Brandenburg, K. & Putz, H. (2005). DIAMOND. Crystal Impact GbR, Postfach 1251, D-53002 Bonn, Germany. Google Scholar
Burla, M. C., Camalli, M., Carrozzini, B., Cascarano, G. L., Giacovazzo, C., Polidori, G. & Spagna, R. (2003). J. Appl. Cryst. 36, 1103. CrossRef IUCr Journals Google Scholar
Khalaji, A., Fejfarová, K. & Dušek, M. (2010a). Acta Chim. Slov. 57, 257–261. CAS PubMed Google Scholar
Khalaji, A. D., Najafi Chermahini, A., Fejfarová, K. & Dušek, M. (2010b). Struct. Chem. 21, 153–157. Web of Science CSD CrossRef CAS Google Scholar
Oxford Diffraction (2009). CrysAlis PRO, Oxford Diffraction Ltd., Oxford, UK. Google Scholar
Petříček, V., Dušek, M. & Palatinus, L. (2007). JANA2006. Institute of Physics, Praha, Czech Republic. Google Scholar

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Volume 66| Part 11| November 2010| Page o2874

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