2-{2-[(2,6-Dichloro­phen­yl)amino]­phen­yl}ethanol

Nasirullah; Ul Islam, N.; Tahir, M.N.; Khan, I.

doi:10.1107/S1600536810054590

organic compounds

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ISSN: 2056-9890

Volume 67| Part 2| February 2011| Page o273

doi:10.1107/S1600536810054590

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2-{2-[(2,6-Dichlorophenyl)amino]phenyl}ethanol

Nasirullah,^a Nazar Ul Islam,^a M. Nawaz Tahir ^b ^* and Ikhtiar Khan ^a

^aInstitute of Chemical Sciences, University of Peshawar, Peshawar, Pakistan, and ^bDepartment of Physics, University of Sargodha, Sargodha, Pakistan
^*Correspondence e-mail: dmntahir_uos@yahoo.com

(Received 26 December 2010; accepted 28 December 2010; online 8 January 2011)

In the title compound, C₁₄H₁₃Cl₂NO, the 2,6-dichloroanilino unit is roughly planar (r.m.s. deviation = 0.0298 Å) and makes a dihedral angle of 67.71 (4)° with the benzene ring containing the ethanol group. The C–C–O fragment is oriented at a dihedral angle of 64.94 (9)° with respect to its parent benzene ring. The molecular conformation is stabilised by a bifurcated N—H⋯(O,Cl) hydrogen bond. C—H⋯π, O—H⋯π and π–π interactions [centroid–centroid distance = 3.5706 (11) Å] stabilize the crystal structure.

Related literature

For related structures, see: Nasirullah et al. (2010 ); Rodriguez et al. (2007 ); Damas et al. (1997 ); Nawaz et al. (2007 ); For graph-set notation, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₁₄H₁₃Cl₂NO
M_r = 282.15
Monoclinic, P 2₁ /c
a = 8.3521 (3) Å
b = 15.0986 (5) Å
c = 10.9225 (5) Å
β = 107.180 (1)°
V = 1315.93 (9) Å³
Z = 4
Mo Kα radiation
μ = 0.48 mm⁻¹
T = 296 K
0.28 × 0.18 × 0.14 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.903, T_max = 0.934
9878 measured reflections
2348 independent reflections
2029 reflections with I > 2σ(I)
R_int = 0.022

Refinement

R[F² > 2σ(F²)] = 0.031
wR(F²) = 0.082
S = 1.06
2348 reflections
167 parameters
All H-atom parameters refined
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.30 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C7–C12 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯Cl1	0.796 (18)	2.628 (18)	2.9888 (16)	109.5 (15)
N1—H1⋯O1	0.796 (18)	2.155 (18)	2.877 (2)	151.0 (18)
O1—H1A⋯Cg1ⁱ	0.82	2.58	3.3465 (19)	156
C3—H3⋯Cg1ⁱⁱ	0.93	2.95	3.791 (2)	152
Symmetry codes: (i) -x+1, -y, -z+1; (ii) $[-x+2, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Data collection: APEX2 (Bruker, 2009 ); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ) and PLATON (Spek, 2009 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ) and PLATON.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810054590/bq2270sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810054590/bq2270Isup2.hkl

checkCIF report

Comment top

The title compound (I, Fig. 1) has been prepared for further derivatization and in continuation to the reduction of carboxylic moieties of some important drugs (Nasirullah et al., 2010) without affecting the medicinally important functional groups.

The crystal structures of (II) i.e., (Z)-3-(4-(2-hydroxyethyl)phenylamino)-1-phenylbut-2-en-1-one (Rodriguez et al., 2007) and (III) 2-[2-(hydroxyethyl)phenoxy]benzoic acid (Damas et al., 1997) have been published previously which seems relavant to the present structure.

In (I), the 2,6-dichloroanilinic moiety A (N1/C1—C6/CL1/CL2) and the benzene ring of 2-phenylethanol B (C7—C12) are planar with r. m. s. deviations of 0.0298 Å and 0.0031 Å, respectively. The ethanol moiety C (C13/C14/O1) is of course planar. The dihedral angles between A/B, A/C and B/C are 67.71 (4)°, 10.40 (20)° and 64.94 (9)°, respectively. The molecules are stabilized as monomers due to intramolecular H-bondings of N—H···Cl and N—H···O types (Table 1, Fig. 1) with S(5) and S(7) ring motifs (Bernstein et al., 1995). In the stabilization of molecules C—H···π and π–π interaction at a distance of 3.5706 (11) Å between the centroids of chloro containing benzene rings play an important role.

Related literature top

For related structures, see: Nasirullah et al. (2010); Rodriguez et al. (2007); Damas et al. (1997); Nawaz et al. (2007); For graph-set notation, see: Bernstein et al. (1995).

Experimental top

A solution of dichlofenac sodium (6.75 mmol) in THF (10 ml) was slowly added to suspension of NaBH₄ (10 mmol) in THF (10 ml), at room temperature. The mixture was stirred until evolution of hydrogen ceased. Iodine (6.75 mmol) in THF (10 ml) was drop wise added to this mixture. When the addition of iodine was complete, the reaction mixture was refluxed for 8 h and cooled to room temperature. 10 ml of 2 N HCl was added and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with 20 ml of 2 N NaOH and then with brine. Finally the ethyl acetate layer was dried over MgSO₄. On evaporation of the solvent 1.3 g of the crude product was obtained. The product was further purified by column chromatography on silica gel. Light yellow needles of (I) were obtained by recrystallization from ethyl acetate and n-hexane. m.p. of pure product:383 K.

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: ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Figures top

Fig. 1. View of (I) with the atom numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. The dotted lines represent the intramolecular H-bonding.

2-{2-[(2,6-Dichlorophenyl)amino]phenyl}ethanol top

Crystal data top

C₁₄H₁₃Cl₂NO	F(000) = 584
M_r = 282.15	D_x = 1.424 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2029 reflections
a = 8.3521 (3) Å	θ = 2.4–25.3°
b = 15.0986 (5) Å	µ = 0.48 mm⁻¹
c = 10.9225 (5) Å	T = 296 K
β = 107.180 (1)°	Needle, light yellow
V = 1315.93 (9) Å³	0.28 × 0.18 × 0.14 mm
Z = 4

Data collection top

Bruker Kappa APEXII CCD diffractometer	2348 independent reflections
Radiation source: fine-focus sealed tube	2029 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.022
Detector resolution: 8.10 pixels mm^-1	θ_max = 25.3°, θ_min = 2.4°
ω scans	h = −10→9
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −18→18
T_min = 0.903, T_max = 0.934	l = −13→11
9878 measured 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)] = 0.031	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.082	All H-atom parameters refined
S = 1.06	w = 1/[σ²(F_o²) + (0.0334P)² + 0.510P] where P = (F_o² + 2F_c²)/3
2348 reflections	(Δ/σ)_max < 0.001
167 parameters	Δρ_max = 0.30 e Å⁻³
0 restraints	Δρ_min = −0.30 e Å⁻³

Crystal data top

C₁₄H₁₃Cl₂NO	V = 1315.93 (9) Å³
M_r = 282.15	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 8.3521 (3) Å	µ = 0.48 mm⁻¹
b = 15.0986 (5) Å	T = 296 K
c = 10.9225 (5) Å	0.28 × 0.18 × 0.14 mm
β = 107.180 (1)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	2348 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	2029 reflections with I > 2σ(I)
T_min = 0.903, T_max = 0.934	R_int = 0.022
9878 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.031	0 restraints
wR(F²) = 0.082	All H-atom parameters refined
S = 1.06	Δρ_max = 0.30 e Å⁻³
2348 reflections	Δρ_min = −0.30 e Å⁻³
167 parameters

Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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
Cl1	0.75713 (7)	−0.13208 (3)	0.78183 (5)	0.0643 (2)
Cl2	1.11847 (6)	0.17019 (3)	0.84323 (5)	0.0563 (2)
O1	0.45224 (19)	0.01954 (11)	0.67674 (19)	0.0809 (6)
N1	0.80367 (17)	0.06112 (10)	0.74340 (13)	0.0391 (4)
C1	0.94805 (19)	0.01500 (11)	0.81022 (15)	0.0363 (5)
C2	0.9460 (2)	−0.07553 (11)	0.83623 (16)	0.0426 (5)
C3	1.0862 (3)	−0.12212 (13)	0.90315 (18)	0.0533 (7)
C4	1.2364 (3)	−0.07878 (14)	0.9456 (2)	0.0586 (7)
C5	1.2460 (2)	0.01071 (14)	0.92471 (19)	0.0540 (7)
C6	1.1029 (2)	0.05691 (11)	0.85975 (16)	0.0415 (5)
C7	0.78660 (18)	0.10202 (10)	0.62459 (14)	0.0322 (4)
C8	0.90748 (19)	0.09185 (10)	0.56114 (16)	0.0373 (5)
C9	0.8907 (2)	0.13202 (11)	0.44481 (17)	0.0438 (6)
C10	0.7518 (2)	0.18261 (12)	0.38800 (17)	0.0476 (6)
C11	0.6306 (2)	0.19269 (11)	0.44974 (17)	0.0428 (5)
C12	0.64417 (18)	0.15399 (10)	0.56786 (16)	0.0353 (5)
C13	0.5069 (2)	0.16759 (12)	0.62982 (19)	0.0469 (6)
C14	0.3779 (2)	0.09453 (15)	0.6051 (2)	0.0599 (7)
H1	0.719 (2)	0.0399 (12)	0.7492 (18)	0.0469*
H1A	0.39115	−0.02359	0.65344	0.0971*
H3	1.07894	−0.18223	0.91928	0.0639*
H4	1.33248	−0.10997	0.98888	0.0703*
H5	1.34815	0.04001	0.95408	0.0648*
H8	1.00146	0.05723	0.59803	0.0448*
H9	0.97366	0.12489	0.40455	0.0525*
H10	0.73968	0.20961	0.30925	0.0571*
H11	0.53635	0.22662	0.41086	0.0514*
H13A	0.45039	0.22296	0.59905	0.0562*
H13B	0.55757	0.17322	0.72162	0.0562*
H14A	0.28150	0.11344	0.63079	0.0719*
H14B	0.34044	0.08021	0.51453	0.0719*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0701 (3)	0.0482 (3)	0.0678 (3)	−0.0170 (2)	0.0101 (3)	−0.0019 (2)
Cl2	0.0524 (3)	0.0452 (3)	0.0661 (3)	−0.0084 (2)	0.0096 (2)	0.0026 (2)
O1	0.0531 (9)	0.0673 (10)	0.1199 (14)	−0.0221 (7)	0.0219 (9)	0.0031 (10)
N1	0.0316 (7)	0.0469 (8)	0.0403 (8)	0.0002 (6)	0.0131 (6)	0.0060 (6)
C1	0.0394 (9)	0.0411 (9)	0.0301 (8)	0.0027 (7)	0.0130 (7)	0.0022 (7)
C2	0.0513 (10)	0.0418 (9)	0.0355 (9)	−0.0022 (8)	0.0142 (7)	0.0006 (7)
C3	0.0689 (13)	0.0453 (10)	0.0473 (11)	0.0117 (9)	0.0197 (9)	0.0107 (8)
C4	0.0536 (12)	0.0628 (13)	0.0569 (12)	0.0191 (10)	0.0126 (9)	0.0153 (10)
C5	0.0389 (10)	0.0667 (13)	0.0536 (11)	0.0038 (9)	0.0093 (8)	0.0069 (9)
C6	0.0417 (9)	0.0442 (9)	0.0392 (9)	0.0014 (7)	0.0127 (7)	0.0045 (7)
C7	0.0313 (8)	0.0298 (7)	0.0341 (8)	−0.0033 (6)	0.0077 (6)	−0.0027 (6)
C8	0.0339 (8)	0.0381 (8)	0.0400 (9)	0.0042 (7)	0.0111 (7)	0.0026 (7)
C9	0.0457 (10)	0.0464 (10)	0.0428 (10)	0.0006 (7)	0.0187 (8)	0.0036 (8)
C10	0.0531 (10)	0.0468 (10)	0.0400 (10)	0.0006 (8)	0.0094 (8)	0.0096 (8)
C11	0.0373 (9)	0.0352 (8)	0.0480 (10)	0.0024 (7)	0.0002 (7)	0.0022 (7)
C12	0.0301 (8)	0.0308 (8)	0.0425 (9)	−0.0019 (6)	0.0067 (7)	−0.0071 (7)
C13	0.0359 (9)	0.0479 (10)	0.0569 (11)	0.0038 (7)	0.0139 (8)	−0.0110 (8)
C14	0.0332 (9)	0.0786 (14)	0.0688 (13)	−0.0077 (9)	0.0163 (9)	−0.0147 (11)

Geometric parameters (Å, º) top

Cl1—C2	1.7369 (18)	C9—C10	1.374 (2)
Cl2—C6	1.7288 (17)	C10—C11	1.381 (2)
O1—C14	1.412 (3)	C11—C12	1.390 (2)
O1—H1A	0.8200	C12—C13	1.508 (2)
N1—C1	1.397 (2)	C13—C14	1.510 (3)
N1—C7	1.406 (2)	C3—H3	0.9300
N1—H1	0.796 (18)	C4—H4	0.9300
C1—C2	1.397 (2)	C5—H5	0.9300
C1—C6	1.397 (2)	C8—H8	0.9300
C2—C3	1.377 (3)	C9—H9	0.9300
C3—C4	1.369 (3)	C10—H10	0.9300
C4—C5	1.377 (3)	C11—H11	0.9300
C5—C6	1.385 (3)	C13—H13A	0.9700
C7—C8	1.392 (2)	C13—H13B	0.9700
C7—C12	1.407 (2)	C14—H14A	0.9700
C8—C9	1.377 (2)	C14—H14B	0.9700

C14—O1—H1A	109.00	C12—C13—C14	114.67 (15)
C1—N1—C7	122.53 (14)	O1—C14—C13	108.25 (16)
C1—N1—H1	114.1 (13)	C2—C3—H3	120.00
C7—N1—H1	113.6 (14)	C4—C3—H3	120.00
N1—C1—C2	122.23 (15)	C3—C4—H4	120.00
N1—C1—C6	122.27 (15)	C5—C4—H4	120.00
C2—C1—C6	115.46 (15)	C4—C5—H5	120.00
C1—C2—C3	123.25 (17)	C6—C5—H5	120.00
Cl1—C2—C1	118.41 (13)	C7—C8—H8	119.00
Cl1—C2—C3	118.34 (14)	C9—C8—H8	119.00
C2—C3—C4	119.10 (18)	C8—C9—H9	120.00
C3—C4—C5	120.4 (2)	C10—C9—H9	120.00
C4—C5—C6	119.71 (18)	C9—C10—H10	121.00
C1—C6—C5	122.03 (16)	C11—C10—H10	121.00
Cl2—C6—C1	119.81 (13)	C10—C11—H11	119.00
Cl2—C6—C5	118.15 (14)	C12—C11—H11	119.00
N1—C7—C12	119.57 (14)	C12—C13—H13A	109.00
N1—C7—C8	121.37 (14)	C12—C13—H13B	109.00
C8—C7—C12	119.06 (14)	C14—C13—H13A	109.00
C7—C8—C9	121.32 (15)	C14—C13—H13B	109.00
C8—C9—C10	120.24 (16)	H13A—C13—H13B	108.00
C9—C10—C11	118.92 (16)	O1—C14—H14A	110.00
C10—C11—C12	122.44 (16)	O1—C14—H14B	110.00
C7—C12—C13	122.31 (15)	C13—C14—H14A	110.00
C7—C12—C11	118.02 (15)	C13—C14—H14B	110.00
C11—C12—C13	119.67 (15)	H14A—C14—H14B	108.00

C7—N1—C1—C2	−117.26 (18)	C4—C5—C6—Cl2	176.57 (16)
C7—N1—C1—C6	65.2 (2)	C4—C5—C6—C1	−2.2 (3)
C1—N1—C7—C8	6.0 (2)	N1—C7—C8—C9	−179.93 (15)
C1—N1—C7—C12	−174.38 (15)	C12—C7—C8—C9	0.4 (2)
N1—C1—C2—Cl1	0.6 (2)	N1—C7—C12—C11	−179.35 (15)
N1—C1—C2—C3	−179.22 (17)	N1—C7—C12—C13	−0.2 (2)
C6—C1—C2—Cl1	178.28 (12)	C8—C7—C12—C11	0.3 (2)
C6—C1—C2—C3	−1.5 (3)	C8—C7—C12—C13	179.44 (15)
N1—C1—C6—Cl2	2.0 (2)	C7—C8—C9—C10	−0.8 (3)
N1—C1—C6—C5	−179.29 (16)	C8—C9—C10—C11	0.3 (3)
C2—C1—C6—Cl2	−175.70 (13)	C9—C10—C11—C12	0.4 (3)
C2—C1—C6—C5	3.0 (2)	C10—C11—C12—C7	−0.7 (2)
Cl1—C2—C3—C4	179.35 (16)	C10—C11—C12—C13	−179.89 (16)
C1—C2—C3—C4	−0.8 (3)	C7—C12—C13—C14	−83.6 (2)
C2—C3—C4—C5	1.8 (3)	C11—C12—C13—C14	95.6 (2)
C3—C4—C5—C6	−0.4 (3)	C12—C13—C14—O1	72.5 (2)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C7–C12 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···Cl1	0.796 (18)	2.628 (18)	2.9888 (16)	109.5 (15)
N1—H1···O1	0.796 (18)	2.155 (18)	2.877 (2)	151.0 (18)
O1—H1A···Cg1ⁱ	0.82	2.58	3.3465 (19)	156
C3—H3···Cg1ⁱⁱ	0.93	2.95	3.791 (2)	152

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

Experimental details

Crystal data
Chemical formula	C₁₄H₁₃Cl₂NO
M_r	282.15
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	8.3521 (3), 15.0986 (5), 10.9225 (5)
β (°)	107.180 (1)
V (Å³)	1315.93 (9)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.48
Crystal size (mm)	0.28 × 0.18 × 0.14

Data collection
Diffractometer	Bruker Kappa APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.903, 0.934
No. of measured, independent and observed [I > 2σ(I)] reflections	9878, 2348, 2029
R_int	0.022
(sin θ/λ)_max (Å⁻¹)	0.600

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.031, 0.082, 1.06
No. of reflections	2348
No. of parameters	167
H-atom treatment	All H-atom parameters refined
Δρ_max, Δρ_min (e Å⁻³)	0.30, −0.30

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009), WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C7–C12 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···Cl1	0.796 (18)	2.628 (18)	2.9888 (16)	109.5 (15)
N1—H1···O1	0.796 (18)	2.155 (18)	2.877 (2)	151.0 (18)
O1—H1A···Cg1ⁱ	0.82	2.58	3.3465 (19)	156
C3—H3···Cg1ⁱⁱ	0.93	2.95	3.791 (2)	152

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

Acknowledgements

The authors acknowledge the provision of funds for the purchase of the diffractometer and encouragement by Dr Muhammad Akram Chaudhary, Vice Chancellor, University of Sargodha, Pakistan.

References

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). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Damas, A. M., Roleira, F. F. & Pinto, M. M. M. (1997). Acta Cryst. C53, 1143–1145. CSD CrossRef CAS Web of Science IUCr Journals Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. CrossRef CAS IUCr Journals Google Scholar
Nasirullah, Islam, N. U., Tahir, M. N. & Khan, I. (2010). Acta Cryst. E66, o2373. Google Scholar
Nawaz, H., Khawar Rauf, M., Ebihara, M. & Badshah, A. (2007). Acta Cryst. E63, o1658–o1659. Web of Science CSD CrossRef IUCr Journals Google Scholar
Rodriguez, M., Santillan, R., Lopez, Y., Farfan, N., Barba, V., Nakatani, K., Baez, E. V. G. & Padilla-Martinez, I. I. (2007). Supramol. Chem. 19, 641–653. CAS 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

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Volume 67| Part 2| February 2011| Page o273

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