2-(3-Fluoro­phen­yl)-5-iodo-7-methyl-3-methyl­sulfinyl-1-benzofuran

Choi, H.D.; Seo, P.J.; Lee, U.

doi:10.1107/S1600536812018697

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 6| June 2012| Page o1612

doi:10.1107/S1600536812018697

Open

access

2-(3-Fluorophenyl)-5-iodo-7-methyl-3-methylsulfinyl-1-benzofuran

Hong Dae Choi,^a Pil Ja Seo ^a and Uk Lee ^b ^*

^aDepartment of Chemistry, Dongeui University, San 24 Kaya-dong, Busanjin-gu, Busan 614-714, Republic of Korea, and ^bDepartment of Chemistry, Pukyong National University, 599-1 Daeyeon 3-dong, Nam-gu, Busan 608-737, Republic of Korea
^*Correspondence e-mail: uklee@pknu.ac.kr

(Received 24 April 2012; accepted 26 April 2012; online 5 May 2012)

In the title compound, C₁₆H₁₂FIO₂S, the 3-fluorophenyl ring makes a dihedral angle of 34.93 (7)° with the mean plane [r.m.s. deviation = 0.019 (1) Å] of the benzofuran fragment. In the crystal, molecules are linked via pairs of I⋯O contacts [3.088 (2) Å] into inversion dimers. These dimers are connected by weak C—H⋯O hydrogen bonds.

Related literature

For background information and the crystal structures of related compounds, see: Choi et al. (2008 , 2010 ). For a review of halogen bonding, see: Politzer et al. (2007 ).

Experimental

Crystal data

C₁₆H₁₂FIO₂S
M_r = 414.22
Monoclinic, P 2₁ /c
a = 7.8169 (1) Å
b = 23.9721 (3) Å
c = 8.0559 (1) Å
β = 99.748 (1)°
V = 1487.78 (3) Å³
Z = 4
Mo Kα radiation
μ = 2.30 mm⁻¹
T = 173 K
0.30 × 0.22 × 0.19 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.570, T_max = 0.746
14066 measured reflections
3424 independent reflections
3226 reflections with I > 2σ(I)
R_int = 0.025

Refinement

R[F² > 2σ(F²)] = 0.021
wR(F²) = 0.052
S = 1.10
3424 reflections
192 parameters
H-atom parameters constrained
Δρ_max = 0.45 e Å⁻³
Δρ_min = −0.55 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C15—H15⋯O2ⁱ	0.95	2.44	3.183 (3)	135
Symmetry code: (i) x-1, y, z.

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 (Farrugia, 1997 ) and DIAMOND (Brandenburg, 1998 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812018697/bt5901sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812018697/bt5901Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812018697/bt5901Isup3.cml

checkCIF report

Comment top

As a part of our ongoing study of 5-iodo-7-methyl-3-methylsulfinyl-1-benzofuran derivatives containing 2-phenyl (Choi et al., 2008) and 2-(4-fluorophenyl) (Choi et al., 2010) substituents, we report herein the crystal structure of the title compound.

In the title molecule (Fig. 1), the benzofuran unit is essentially planar, with a mean deviation of 0.019 (1) Å from the least-squares plane defined by the nine constituent atoms. The dihedral angle between the 3-fluorophenyl ring and the mean plane of the benzofuran fragment is 34.93 (7)°. In the crystal structure (Fig. 2), molecules are linked via pairs of I···O halogen-bondings (Politzer et al., 2007) between the iodine atom and the O atom of the S═O unit [I1···O2ⁱ = 3.088 (2) Å, C4—I1···O2ⁱ = 169.86 (6)°], forming inversion dimers. These dimers are connected by weak intermolecular C—H···O hydrogen bonds (Table 1).

Related literature top

For background information and the crystal structures of related compounds, see: Choi et al. (2008, 2010). For a review of halogen bonding, see: Politzer et al. (2007).

Experimental top

3-Chloroperoxybenzoic acid (77%, 202 mg, 0.9 mmol) was added in small portions to a stirred solution of 2-(3-fluorophenyl)-5-iodo-7-methyl-3-methylsulfanyl-1-benzofuran (326 mg, 0.8 mmol) in dichloromethane (30 mL) at 273 K. After being stirred at room temperature for 4h, the mixture was washed with saturated sodium bicarbonate solution and the organic layer was separated, dried over magnesium sulfate, filtered and concentrated at reduced pressure. The residue was purified by column chromatography (hexane/ethyl acetate, 1:1 v/v) to afford the title compound as a colorless solid [yield 70%, m.p. 459–460 K; R_f = 0.56 (hexane?ethyl acetate, 1:1 v/v)]. Single crystals suitable for X-ray diffraction were prepared by slow evaporation of a solution of the title compound in ethyl acetate at room temperature.

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 (Farrugia, 1997) and DIAMOND (Brandenburg, 1998); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound with the atom numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are presented as small spheres of arbitrary radius.
	Fig. 2. A view of the C—H···O and I···O interactions (dotted lines) in the crystal structure of the title compound. H atoms non-participating in hydrogen-bonding were omitted for clarity. [Symmetry codes: (i) - x + 2, - y + 1, - z + 2; (ii) x - 1, y, z; (iii) x + 1, y, z.]

2-(3-Fluorophenyl)-5-iodo-7-methyl-3-methylsulfinyl-1-benzofuran top

Crystal data top

C₁₆H₁₂FIO₂S	F(000) = 808
M_r = 414.22	D_x = 1.849 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 8987 reflections
a = 7.8169 (1) Å	θ = 2.7–27.5°
b = 23.9721 (3) Å	µ = 2.30 mm⁻¹
c = 8.0559 (1) Å	T = 173 K
β = 99.748 (1)°	Block, colourless
V = 1487.78 (3) Å³	0.30 × 0.22 × 0.19 mm
Z = 4

Data collection top

Bruker SMART APEXII CCD diffractometer	3424 independent reflections
Radiation source: rotating anode	3226 reflections with I > 2σ(I)
Graphite multilayer monochromator	R_int = 0.025
Detector resolution: 10.0 pixels mm^-1	θ_max = 27.5°, θ_min = 1.7°
ϕ and ω scans	h = −10→8
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −31→30
T_min = 0.570, T_max = 0.746	l = −10→10
14066 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)] = 0.021	Hydrogen site location: difference Fourier map
wR(F²) = 0.052	H-atom parameters constrained
S = 1.10	w = 1/[σ²(F_o²) + (0.0225P)² + 1.0726P] where P = (F_o² + 2F_c²)/3
3424 reflections	(Δ/σ)_max = 0.002
192 parameters	Δρ_max = 0.45 e Å⁻³
0 restraints	Δρ_min = −0.55 e Å⁻³

Crystal data top

C₁₆H₁₂FIO₂S	V = 1487.78 (3) Å³
M_r = 414.22	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 7.8169 (1) Å	µ = 2.30 mm⁻¹
b = 23.9721 (3) Å	T = 173 K
c = 8.0559 (1) Å	0.30 × 0.22 × 0.19 mm
β = 99.748 (1)°

Data collection top

Bruker SMART APEXII CCD diffractometer	3424 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	3226 reflections with I > 2σ(I)
T_min = 0.570, T_max = 0.746	R_int = 0.025
14066 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.021	0 restraints
wR(F²) = 0.052	H-atom parameters constrained
S = 1.10	Δρ_max = 0.45 e Å⁻³
3424 reflections	Δρ_min = −0.55 e Å⁻³
192 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	0.830625 (17)	0.412987 (6)	1.026115 (17)	0.02457 (6)
S1	0.70761 (6)	0.66239 (2)	0.72019 (6)	0.02102 (11)
F1	−0.11935 (17)	0.70760 (6)	0.33734 (19)	0.0382 (3)
O1	0.31305 (17)	0.56234 (6)	0.56108 (17)	0.0187 (3)
O2	0.88641 (19)	0.64247 (7)	0.7119 (2)	0.0298 (3)
C1	0.5622 (3)	0.60638 (8)	0.6682 (2)	0.0192 (4)
C2	0.5730 (2)	0.54990 (8)	0.7341 (2)	0.0185 (4)
C3	0.6967 (3)	0.51834 (8)	0.8398 (3)	0.0212 (4)
H3	0.8058	0.5336	0.8886	0.025*
C4	0.6524 (3)	0.46397 (8)	0.8699 (2)	0.0204 (4)
C5	0.4901 (3)	0.44112 (8)	0.8021 (2)	0.0207 (4)
H5	0.4652	0.4037	0.8283	0.025*
C6	0.3652 (2)	0.47188 (8)	0.6978 (2)	0.0193 (4)
C7	0.4151 (2)	0.52550 (8)	0.6654 (2)	0.0182 (4)
C8	0.4067 (2)	0.61080 (8)	0.5635 (2)	0.0177 (4)
C9	0.1873 (3)	0.44943 (9)	0.6296 (3)	0.0272 (5)
H9A	0.1000	0.4706	0.6774	0.041*
H9B	0.1813	0.4100	0.6603	0.041*
H9C	0.1648	0.4531	0.5067	0.041*
C10	0.3182 (2)	0.65543 (8)	0.4579 (2)	0.0184 (4)
C11	0.4081 (3)	0.69255 (9)	0.3707 (3)	0.0240 (4)
H11	0.5301	0.6890	0.3772	0.029*
C12	0.3186 (3)	0.73475 (10)	0.2744 (3)	0.0301 (5)
H12	0.3802	0.7600	0.2153	0.036*
C13	0.1406 (3)	0.74046 (10)	0.2636 (3)	0.0300 (5)
H13	0.0792	0.7698	0.2001	0.036*
C14	0.0562 (3)	0.70246 (9)	0.3474 (3)	0.0253 (4)
C15	0.1381 (3)	0.65996 (9)	0.4442 (2)	0.0203 (4)
H15	0.0743	0.6344	0.5002	0.024*
C16	0.6965 (3)	0.66712 (10)	0.9404 (3)	0.0308 (5)
H16A	0.7382	0.6322	0.9964	0.046*
H16B	0.5760	0.6736	0.9545	0.046*
H16C	0.7691	0.6981	0.9905	0.046*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
I1	0.02277 (8)	0.02225 (8)	0.02801 (8)	0.00522 (5)	0.00230 (6)	0.00455 (5)
S1	0.0205 (2)	0.0182 (2)	0.0234 (2)	−0.00496 (18)	0.00100 (19)	0.00187 (18)
F1	0.0224 (7)	0.0458 (9)	0.0453 (8)	0.0121 (6)	0.0022 (6)	0.0103 (7)
O1	0.0175 (6)	0.0161 (7)	0.0213 (6)	−0.0019 (5)	0.0002 (5)	0.0015 (5)
O2	0.0183 (7)	0.0381 (9)	0.0330 (8)	−0.0056 (6)	0.0044 (6)	−0.0003 (7)
C1	0.0189 (9)	0.0177 (9)	0.0211 (9)	−0.0020 (7)	0.0033 (7)	0.0010 (7)
C2	0.0185 (9)	0.0158 (9)	0.0215 (9)	−0.0006 (7)	0.0045 (7)	−0.0007 (7)
C3	0.0166 (9)	0.0213 (10)	0.0250 (10)	−0.0002 (7)	0.0018 (8)	−0.0002 (8)
C4	0.0210 (9)	0.0201 (10)	0.0201 (9)	0.0040 (7)	0.0033 (8)	0.0024 (7)
C5	0.0224 (10)	0.0163 (10)	0.0246 (10)	−0.0008 (7)	0.0071 (8)	0.0002 (7)
C6	0.0191 (9)	0.0180 (10)	0.0211 (9)	−0.0021 (7)	0.0040 (7)	−0.0020 (7)
C7	0.0169 (9)	0.0185 (10)	0.0191 (9)	0.0004 (7)	0.0032 (7)	0.0007 (7)
C8	0.0177 (9)	0.0168 (9)	0.0193 (9)	−0.0019 (7)	0.0050 (7)	0.0000 (7)
C9	0.0212 (10)	0.0232 (11)	0.0353 (11)	−0.0064 (8)	−0.0002 (9)	0.0009 (9)
C10	0.0203 (9)	0.0169 (9)	0.0173 (9)	−0.0003 (7)	0.0012 (7)	−0.0003 (7)
C11	0.0222 (10)	0.0252 (11)	0.0249 (10)	−0.0013 (8)	0.0050 (8)	0.0026 (8)
C12	0.0346 (12)	0.0257 (11)	0.0305 (11)	−0.0036 (9)	0.0070 (9)	0.0091 (9)
C13	0.0361 (12)	0.0248 (11)	0.0274 (10)	0.0060 (9)	0.0004 (9)	0.0068 (9)
C14	0.0213 (10)	0.0283 (11)	0.0251 (10)	0.0064 (8)	0.0010 (8)	−0.0002 (8)
C15	0.0210 (9)	0.0198 (10)	0.0200 (9)	−0.0009 (7)	0.0030 (7)	−0.0011 (7)
C16	0.0372 (12)	0.0309 (12)	0.0245 (10)	−0.0044 (10)	0.0063 (9)	−0.0049 (9)

Geometric parameters (Å, º) top

I1—C4	2.1034 (19)	C6—C9	1.505 (3)
I1—O2ⁱ	3.0876 (16)	C8—C10	1.466 (3)
S1—O2	1.4891 (16)	C9—H9A	0.9800
S1—C1	1.763 (2)	C9—H9B	0.9800
S1—C16	1.795 (2)	C9—H9C	0.9800
F1—C14	1.366 (2)	C10—C11	1.395 (3)
O1—C8	1.371 (2)	C10—C15	1.398 (3)
O1—C7	1.376 (2)	C11—C12	1.390 (3)
C1—C8	1.361 (3)	C11—H11	0.9500
C1—C2	1.451 (3)	C12—C13	1.386 (3)
C2—C7	1.393 (3)	C12—H12	0.9500
C2—C3	1.397 (3)	C13—C14	1.368 (3)
C3—C4	1.380 (3)	C13—H13	0.9500
C3—H3	0.9500	C14—C15	1.374 (3)
C4—C5	1.405 (3)	C15—H15	0.9500
C5—C6	1.388 (3)	C16—H16A	0.9800
C5—H5	0.9500	C16—H16B	0.9800
C6—C7	1.381 (3)	C16—H16C	0.9800

C4—I1—O2ⁱ	169.86 (6)	C6—C9—H9B	109.5
O2—S1—C1	108.51 (9)	H9A—C9—H9B	109.5
O2—S1—C16	105.52 (10)	C6—C9—H9C	109.5
C1—S1—C16	98.38 (10)	H9A—C9—H9C	109.5
C8—O1—C7	106.39 (14)	H9B—C9—H9C	109.5
C8—C1—C2	106.86 (17)	C11—C10—C15	119.85 (18)
C8—C1—S1	124.05 (15)	C11—C10—C8	121.95 (18)
C2—C1—S1	128.91 (14)	C15—C10—C8	118.20 (17)
C7—C2—C3	119.33 (18)	C12—C11—C10	119.7 (2)
C7—C2—C1	104.67 (16)	C12—C11—H11	120.1
C3—C2—C1	136.00 (18)	C10—C11—H11	120.1
C4—C3—C2	116.76 (18)	C13—C12—C11	120.8 (2)
C4—C3—H3	121.6	C13—C12—H12	119.6
C2—C3—H3	121.6	C11—C12—H12	119.6
C3—C4—C5	122.44 (18)	C14—C13—C12	117.8 (2)
C3—C4—I1	119.57 (14)	C14—C13—H13	121.1
C5—C4—I1	117.98 (15)	C12—C13—H13	121.1
C6—C5—C4	121.68 (19)	F1—C14—C13	118.30 (19)
C6—C5—H5	119.2	F1—C14—C15	117.87 (19)
C4—C5—H5	119.2	C13—C14—C15	123.8 (2)
C7—C6—C5	114.62 (18)	C14—C15—C10	117.96 (19)
C7—C6—C9	122.47 (18)	C14—C15—H15	121.0
C5—C6—C9	122.89 (19)	C10—C15—H15	121.0
O1—C7—C6	124.02 (17)	S1—C16—H16A	109.5
O1—C7—C2	110.87 (17)	S1—C16—H16B	109.5
C6—C7—C2	125.11 (18)	H16A—C16—H16B	109.5
C1—C8—O1	111.17 (17)	S1—C16—H16C	109.5
C1—C8—C10	134.49 (18)	H16A—C16—H16C	109.5
O1—C8—C10	114.33 (16)	H16B—C16—H16C	109.5
C6—C9—H9A	109.5

O2—S1—C1—C8	−136.08 (17)	C3—C2—C7—O1	−178.14 (17)
C16—S1—C1—C8	114.37 (19)	C1—C2—C7—O1	1.4 (2)
O2—S1—C1—C2	49.5 (2)	C3—C2—C7—C6	2.5 (3)
C16—S1—C1—C2	−60.0 (2)	C1—C2—C7—C6	−177.92 (19)
C8—C1—C2—C7	−2.2 (2)	C2—C1—C8—O1	2.2 (2)
S1—C1—C2—C7	172.98 (16)	S1—C1—C8—O1	−173.22 (14)
C8—C1—C2—C3	177.3 (2)	C2—C1—C8—C10	−179.2 (2)
S1—C1—C2—C3	−7.6 (4)	S1—C1—C8—C10	5.3 (3)
C7—C2—C3—C4	−0.2 (3)	C7—O1—C8—C1	−1.4 (2)
C1—C2—C3—C4	−179.6 (2)	C7—O1—C8—C10	179.76 (16)
C2—C3—C4—C5	−1.5 (3)	C1—C8—C10—C11	37.1 (3)
C2—C3—C4—I1	179.60 (14)	O1—C8—C10—C11	−144.37 (18)
O2ⁱ—I1—C4—C3	31.2 (5)	C1—C8—C10—C15	−143.5 (2)
O2ⁱ—I1—C4—C5	−147.7 (3)	O1—C8—C10—C15	35.0 (2)
C3—C4—C5—C6	1.1 (3)	C15—C10—C11—C12	1.7 (3)
I1—C4—C5—C6	−179.97 (15)	C8—C10—C11—C12	−178.94 (19)
C4—C5—C6—C7	1.0 (3)	C10—C11—C12—C13	−0.1 (3)
C4—C5—C6—C9	−177.2 (2)	C11—C12—C13—C14	−1.5 (3)
C8—O1—C7—C6	179.23 (18)	C12—C13—C14—F1	−179.9 (2)
C8—O1—C7—C2	−0.1 (2)	C12—C13—C14—C15	1.5 (3)
C5—C6—C7—O1	177.90 (18)	F1—C14—C15—C10	−178.52 (18)
C9—C6—C7—O1	−3.9 (3)	C13—C14—C15—C10	0.1 (3)
C5—C6—C7—C2	−2.8 (3)	C11—C10—C15—C14	−1.7 (3)
C9—C6—C7—C2	175.3 (2)	C8—C10—C15—C14	178.90 (18)

Symmetry code: (i) −x+2, −y+1, −z+2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15···O2ⁱⁱ	0.95	2.44	3.183 (3)	135

Symmetry code: (ii) x−1, y, z.

Experimental details

Crystal data
Chemical formula	C₁₆H₁₂FIO₂S
M_r	414.22
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	173
a, b, c (Å)	7.8169 (1), 23.9721 (3), 8.0559 (1)
β (°)	99.748 (1)
V (Å³)	1487.78 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	2.30
Crystal size (mm)	0.30 × 0.22 × 0.19

Data collection
Diffractometer	Bruker SMART APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.570, 0.746
No. of measured, independent and observed [I > 2σ(I)] reflections	14066, 3424, 3226
R_int	0.025
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.021, 0.052, 1.10
No. of reflections	3424
No. of parameters	192
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.45, −0.55

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 1998).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15···O2ⁱ	0.95	2.44	3.183 (3)	135.0

Symmetry code: (i) x−1, y, z.

References

Brandenburg, K. (1998). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Bruker (2009). APEX2, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Choi, H. D., Seo, P. J., Kim, B. K., Son, B. W. & Lee, U. (2008). Acta Cryst. E64, o1116. Web of Science CSD CrossRef IUCr Journals Google Scholar
Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2010). Acta Cryst. E66, o1680. Web of Science CSD CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Politzer, P., Lane, P., Concha, M. C., Ma, Y. & Murray, J. S. (2007). J. Mol. Model. 13, 305–311. Web of Science CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. 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.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 6| June 2012| Page o1612

doi:10.1107/S1600536812018697

Open

access