5-Bromo-2,7-dimethyl-3-(4-methyl­phenyl­sulfon­yl)-1-benzo­furan

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

doi:10.1107/S1600536814007181

organic compounds

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ISSN: 2056-9890

Volume 70| Part 5| May 2014| Page o520

doi:10.1107/S1600536814007181

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5-Bromo-2,7-dimethyl-3-(4-methylphenylsulfonyl)-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 25 March 2014; accepted 1 April 2014; online 5 April 2014)

In the title compound, C₁₇H₁₅BrO₃S, the dihedral angle between the mean planes of the benzofuran and 4-methylphenyl rings is 76.43 (5)°. In the crystal, molecules are linked via pairs of C—H⋯O hydrogen bonds into inversion dimers that are further linked by Br⋯Br [3.6517 (4) Å] contacts about inversion centers into supramolecular sheets that lie parallel to (111).

CCDC reference: 994776

Related literature

For background information and the crystal structures of related compounds, see: Choi et al. (2011 , 2012 , 2013 ).

Experimental

Crystal data

C₁₇H₁₅BrO₃S
M_r = 379.26
Triclinic, $[P \overline 1]$
a = 8.1554 (2) Å
b = 9.9790 (2) Å
c = 10.1260 (2) Å
α = 77.410 (1)°
β = 77.114 (1)°
γ = 76.009 (1)°
V = 767.68 (3) Å³
Z = 2
Mo Kα radiation
μ = 2.82 mm⁻¹
T = 173 K
0.34 × 0.32 × 0.23 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.543, T_max = 0.746
14016 measured reflections
3812 independent reflections
3336 reflections with I > 2σ(I)
R_int = 0.033

Refinement

R[F² > 2σ(F²)] = 0.028
wR(F²) = 0.073
S = 1.04
3812 reflections
202 parameters
H-atom parameters constrained
Δρ_max = 0.36 e Å⁻³
Δρ_min = −0.42 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13—H13⋯O2ⁱ	0.95	2.54	3.330 (2)	140
Symmetry code: (i) -x+1, -y+1, -z+1.

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, 2012 ) and DIAMOND (Brandenburg, 1998 ); software used to prepare material for publication: SHELXL97.

Supporting information

CCDC reference: 994776

Crystal structure: contains datablock I. DOI: 10.1107/S1600536814007181/gg2139sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814007181/gg2139Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536814007181/gg2139Isup3.cml

checkCIF report

Comment top

As a part of our ongoing study of 5-bromo-2,7-dimethyl-1-benzofuran derivatives containing cyclohexylsulfonyl (Choi et al., 2011), 4-fluorophenylsulfonyl (Choi et al., 2012) and 4-methylphenylsulfinyl (Choi et al., 2013) substituents in the 3-position, we report here on the crystal structure of the title compound.

In the title molecule (Fig. 1), the benzofuran ring system is essentially planar, with a mean deviation of 0.008 (1) Å from the least-squares plane defined by the nine constituent atoms. The 4-methylphenyl ring is essentially planar, with a mean deviation of 0.005 (1) Å from the least-squares plane defined by the six constituent atoms. The dihedral angle formed by the benzofuran ring system and the 4-methylphenyl ring is 76.43 (5)°. In the crystal structure (Fig. 2), molecules are linked via pairs of C—H···O hydrogen bonds (Table 1) into inversion dimers.

In the crystal, molecules are linked via pairs of C—H···O hydrogen bonds into inversion dimers that are further linked by C—H···O interactions and Br···Br [3.6517 (4) Å] contacts about inversion centers into supramolecular sheets that lie parallel with the (111) plane.

Related literature top

For background information and the crystal structures of related compounds, see: Choi et al. (2011, 2012, 2013).

Experimental top

3-Chloroperoxybenzoic acid (77%, 448 mg, 2.0 mmol) was added in small portions to a stirred solution of 5-bromo-2,7-dimethyl-3-(4-methylphenylsulfanyl)-1-benzofuran (312 mg, 0.9 mmol) in dichloromethane (40 mL) at 273 K. After being stirred at room temperature for 8h, 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, 4:1 v/v) to afford the title compound as a colorless solid [yield 69%, m.p. 474-475 K; R_f = 0.48 (hexane-ethyl acetate, 4:1 v/v)]. Single crystals suitable for X-ray diffraction were prepared by slow vaporation 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 for Windows (Farrugia, 2012) and DIAMOND (Brandenburg, 1998); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title molecule with the atom numbering scheme. The displacement ellipsoids are drawn at the 50% probability level. The hydrogen atoms are presented as small spheres of arbitrary radius.
	Fig. 2. A view of the C—H···O and Br···Br 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 + 1, - y + 2, - z; (ii) - x + 1, - y + 1, - z + 1]

5-Bromo-2,7-dimethyl-3-(4-methylphenylsulfonyl)-1-benzofuran top

Crystal data top

C₁₇H₁₅BrO₃S	Z = 2
M_r = 379.26	F(000) = 384
Triclinic, P1	D_x = 1.641 Mg m⁻³
Hall symbol: -P 1	Melting point = 475–474 K
a = 8.1554 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.9790 (2) Å	Cell parameters from 6793 reflections
c = 10.1260 (2) Å	θ = 2.7–28.3°
α = 77.410 (1)°	µ = 2.82 mm⁻¹
β = 77.114 (1)°	T = 173 K
γ = 76.009 (1)°	Block, colourless
V = 767.68 (3) Å³	0.34 × 0.32 × 0.23 mm

Data collection top

Bruker SMART APEXII CCD diffractometer	3812 independent reflections
Radiation source: rotating anode	3336 reflections with I > 2σ(I)
Graphite multilayer monochromator	R_int = 0.033
Detector resolution: 10.0 pixels mm^-1	θ_max = 28.4°, θ_min = 2.1°
ϕ and ω scans	h = −10→10
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −13→13
T_min = 0.543, T_max = 0.746	l = −13→13
14016 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)] = 0.028	Hydrogen site location: difference Fourier map
wR(F²) = 0.073	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0353P)² + 0.3958P] where P = (F_o² + 2F_c²)/3
3812 reflections	(Δ/σ)_max = 0.001
202 parameters	Δρ_max = 0.36 e Å⁻³
0 restraints	Δρ_min = −0.42 e Å⁻³

Crystal data top

C₁₇H₁₅BrO₃S	γ = 76.009 (1)°
M_r = 379.26	V = 767.68 (3) Å³
Triclinic, P1	Z = 2
a = 8.1554 (2) Å	Mo Kα radiation
b = 9.9790 (2) Å	µ = 2.82 mm⁻¹
c = 10.1260 (2) Å	T = 173 K
α = 77.410 (1)°	0.34 × 0.32 × 0.23 mm
β = 77.114 (1)°

Data collection top

Bruker SMART APEXII CCD diffractometer	3812 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	3336 reflections with I > 2σ(I)
T_min = 0.543, T_max = 0.746	R_int = 0.033
14016 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.028	0 restraints
wR(F²) = 0.073	H-atom parameters constrained
S = 1.04	Δρ_max = 0.36 e Å⁻³
3812 reflections	Δρ_min = −0.42 e Å⁻³
202 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
Br1	0.50946 (3)	0.81656 (2)	−0.00546 (2)	0.03262 (8)
S1	0.91173 (6)	0.31301 (5)	0.35042 (4)	0.02099 (10)
O1	0.93317 (17)	0.24115 (13)	−0.01983 (13)	0.0222 (3)
O2	0.88773 (18)	0.45707 (15)	0.36343 (14)	0.0274 (3)
O3	1.06161 (18)	0.21433 (15)	0.38771 (14)	0.0287 (3)
C1	0.9028 (2)	0.31299 (19)	0.18034 (17)	0.0199 (3)
C2	0.8119 (2)	0.42615 (19)	0.09103 (18)	0.0195 (3)
C3	0.7156 (2)	0.56082 (19)	0.10102 (19)	0.0225 (4)
H3	0.6982	0.6000	0.1818	0.027*
C4	0.6470 (2)	0.63398 (19)	−0.01324 (19)	0.0232 (4)
C5	0.6705 (3)	0.5809 (2)	−0.13421 (19)	0.0251 (4)
H5	0.6202	0.6369	−0.2094	0.030*
C6	0.7667 (2)	0.4471 (2)	−0.14618 (18)	0.0230 (4)
C7	0.8346 (2)	0.37528 (19)	−0.03066 (18)	0.0205 (3)
C8	0.9720 (2)	0.2055 (2)	0.10962 (18)	0.0217 (4)
C9	0.7931 (3)	0.3831 (2)	−0.2723 (2)	0.0308 (4)
H9A	0.9106	0.3284	−0.2890	0.046*
H9B	0.7745	0.4576	−0.3516	0.046*
H9C	0.7114	0.3215	−0.2585	0.046*
C10	1.0746 (3)	0.0626 (2)	0.1429 (2)	0.0284 (4)
H10A	1.0974	0.0473	0.2366	0.043*
H10B	1.1838	0.0523	0.0778	0.043*
H10C	1.0108	−0.0065	0.1363	0.043*
C11	0.7293 (2)	0.25019 (19)	0.44768 (18)	0.0206 (3)
C12	0.5677 (3)	0.3361 (2)	0.4457 (2)	0.0270 (4)
H12	0.5553	0.4269	0.3908	0.032*
C13	0.4250 (3)	0.2879 (2)	0.5248 (2)	0.0295 (4)
H13	0.3142	0.3461	0.5232	0.035*
C14	0.4410 (3)	0.1561 (2)	0.60634 (19)	0.0267 (4)
C15	0.6032 (3)	0.0716 (2)	0.6056 (2)	0.0303 (4)
H15	0.6155	−0.0193	0.6604	0.036*
C16	0.7476 (3)	0.1173 (2)	0.5263 (2)	0.0269 (4)
H16	0.8580	0.0580	0.5260	0.032*
C17	0.2839 (3)	0.1074 (3)	0.6937 (2)	0.0375 (5)
H17A	0.3131	0.0064	0.7278	0.056*
H17B	0.1937	0.1266	0.6384	0.056*
H17C	0.2427	0.1575	0.7718	0.056*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.03337 (12)	0.01974 (11)	0.03988 (13)	−0.00075 (8)	−0.00655 (9)	−0.00013 (8)
S1	0.0221 (2)	0.0245 (2)	0.0167 (2)	−0.00315 (17)	−0.00529 (16)	−0.00419 (16)
O1	0.0252 (7)	0.0221 (6)	0.0191 (6)	−0.0024 (5)	−0.0035 (5)	−0.0065 (5)
O2	0.0345 (8)	0.0283 (7)	0.0229 (7)	−0.0090 (6)	−0.0053 (6)	−0.0089 (6)
O3	0.0226 (7)	0.0357 (8)	0.0258 (7)	−0.0006 (6)	−0.0085 (5)	−0.0031 (6)
C1	0.0201 (8)	0.0221 (9)	0.0162 (8)	−0.0025 (7)	−0.0034 (6)	−0.0026 (7)
C2	0.0199 (8)	0.0211 (8)	0.0173 (8)	−0.0053 (7)	−0.0027 (6)	−0.0021 (7)
C3	0.0254 (9)	0.0224 (9)	0.0199 (8)	−0.0060 (7)	−0.0024 (7)	−0.0042 (7)
C4	0.0231 (9)	0.0184 (8)	0.0257 (9)	−0.0044 (7)	−0.0026 (7)	−0.0004 (7)
C5	0.0277 (10)	0.0266 (10)	0.0209 (9)	−0.0087 (8)	−0.0067 (7)	0.0020 (7)
C6	0.0252 (9)	0.0272 (10)	0.0182 (8)	−0.0094 (8)	−0.0044 (7)	−0.0023 (7)
C7	0.0216 (8)	0.0207 (8)	0.0190 (8)	−0.0054 (7)	−0.0023 (7)	−0.0031 (7)
C8	0.0206 (9)	0.0248 (9)	0.0196 (8)	−0.0044 (7)	−0.0036 (7)	−0.0037 (7)
C9	0.0392 (12)	0.0361 (11)	0.0195 (9)	−0.0089 (9)	−0.0079 (8)	−0.0057 (8)
C10	0.0274 (10)	0.0236 (9)	0.0318 (10)	0.0015 (8)	−0.0057 (8)	−0.0072 (8)
C11	0.0222 (9)	0.0242 (9)	0.0154 (8)	−0.0031 (7)	−0.0039 (7)	−0.0045 (7)
C12	0.0278 (10)	0.0226 (9)	0.0269 (10)	−0.0009 (8)	−0.0055 (8)	−0.0007 (8)
C13	0.0227 (9)	0.0318 (11)	0.0301 (10)	0.0014 (8)	−0.0038 (8)	−0.0058 (8)
C14	0.0278 (10)	0.0326 (10)	0.0192 (9)	−0.0059 (8)	−0.0020 (7)	−0.0060 (8)
C15	0.0316 (11)	0.0264 (10)	0.0273 (10)	−0.0037 (8)	−0.0049 (8)	0.0041 (8)
C16	0.0235 (9)	0.0274 (10)	0.0252 (9)	0.0011 (8)	−0.0054 (8)	−0.0005 (8)
C17	0.0312 (11)	0.0460 (13)	0.0328 (11)	−0.0127 (10)	0.0004 (9)	−0.0028 (10)

Geometric parameters (Å, º) top

Br1—C4	1.9023 (19)	C9—H9A	0.9800
Br1—Br1ⁱ	3.6517 (4)	C9—H9B	0.9800
S1—O2	1.4343 (14)	C9—H9C	0.9800
S1—O3	1.4381 (14)	C10—H10A	0.9800
S1—C1	1.7400 (17)	C10—H10B	0.9800
S1—C11	1.7618 (19)	C10—H10C	0.9800
O1—C8	1.368 (2)	C11—C16	1.383 (3)
O1—C7	1.380 (2)	C11—C12	1.390 (3)
C1—C8	1.358 (3)	C12—C13	1.384 (3)
C1—C2	1.446 (2)	C12—H12	0.9500
C2—C7	1.391 (2)	C13—C14	1.385 (3)
C2—C3	1.395 (3)	C13—H13	0.9500
C3—C4	1.381 (3)	C14—C15	1.385 (3)
C3—H3	0.9500	C14—C17	1.507 (3)
C4—C5	1.395 (3)	C15—C16	1.385 (3)
C5—C6	1.391 (3)	C15—H15	0.9500
C5—H5	0.9500	C16—H16	0.9500
C6—C7	1.386 (3)	C17—H17A	0.9800
C6—C9	1.500 (3)	C17—H17B	0.9800
C8—C10	1.479 (3)	C17—H17C	0.9800

C4—Br1—Br1ⁱ	147.64 (6)	H9A—C9—H9B	109.5
O2—S1—O3	119.77 (9)	C6—C9—H9C	109.5
O2—S1—C1	106.40 (8)	H9A—C9—H9C	109.5
O3—S1—C1	109.32 (9)	H9B—C9—H9C	109.5
O2—S1—C11	107.59 (9)	C8—C10—H10A	109.5
O3—S1—C11	107.93 (9)	C8—C10—H10B	109.5
C1—S1—C11	104.85 (8)	H10A—C10—H10B	109.5
C8—O1—C7	107.07 (14)	C8—C10—H10C	109.5
C8—C1—C2	107.66 (15)	H10A—C10—H10C	109.5
C8—C1—S1	126.61 (14)	H10B—C10—H10C	109.5
C2—C1—S1	125.66 (14)	C16—C11—C12	120.53 (18)
C7—C2—C3	119.23 (17)	C16—C11—S1	120.14 (14)
C7—C2—C1	104.64 (16)	C12—C11—S1	119.33 (15)
C3—C2—C1	136.13 (16)	C13—C12—C11	119.24 (19)
C4—C3—C2	116.18 (17)	C13—C12—H12	120.4
C4—C3—H3	121.9	C11—C12—H12	120.4
C2—C3—H3	121.9	C12—C13—C14	121.07 (19)
C3—C4—C5	123.76 (18)	C12—C13—H13	119.5
C3—C4—Br1	118.52 (14)	C14—C13—H13	119.5
C5—C4—Br1	117.71 (14)	C13—C14—C15	118.72 (18)
C6—C5—C4	120.83 (18)	C13—C14—C17	119.98 (19)
C6—C5—H5	119.6	C15—C14—C17	121.30 (19)
C4—C5—H5	119.6	C16—C15—C14	121.17 (19)
C7—C6—C5	114.64 (17)	C16—C15—H15	119.4
C7—C6—C9	122.07 (18)	C14—C15—H15	119.4
C5—C6—C9	123.28 (17)	C11—C16—C15	119.25 (18)
O1—C7—C6	124.36 (16)	C11—C16—H16	120.4
O1—C7—C2	110.27 (15)	C15—C16—H16	120.4
C6—C7—C2	125.36 (18)	C14—C17—H17A	109.5
C1—C8—O1	110.36 (16)	C14—C17—H17B	109.5
C1—C8—C10	134.25 (17)	H17A—C17—H17B	109.5
O1—C8—C10	115.38 (16)	C14—C17—H17C	109.5
C6—C9—H9A	109.5	H17A—C17—H17C	109.5
C6—C9—H9B	109.5	H17B—C17—H17C	109.5

O2—S1—C1—C8	156.87 (17)	C3—C2—C7—O1	179.91 (15)
O3—S1—C1—C8	26.20 (19)	C1—C2—C7—O1	−0.49 (19)
C11—S1—C1—C8	−89.30 (18)	C3—C2—C7—C6	−0.9 (3)
O2—S1—C1—C2	−26.54 (18)	C1—C2—C7—C6	178.71 (17)
O3—S1—C1—C2	−157.20 (15)	C2—C1—C8—O1	0.3 (2)
C11—S1—C1—C2	87.29 (17)	S1—C1—C8—O1	177.42 (13)
C8—C1—C2—C7	0.1 (2)	C2—C1—C8—C10	−178.7 (2)
S1—C1—C2—C7	−177.03 (14)	S1—C1—C8—C10	−1.6 (3)
C8—C1—C2—C3	179.6 (2)	C7—O1—C8—C1	−0.6 (2)
S1—C1—C2—C3	2.5 (3)	C7—O1—C8—C10	178.59 (16)
C7—C2—C3—C4	0.8 (3)	O2—S1—C11—C16	−139.02 (15)
C1—C2—C3—C4	−178.64 (19)	O3—S1—C11—C16	−8.47 (18)
C2—C3—C4—C5	−0.5 (3)	C1—S1—C11—C16	107.99 (16)
C2—C3—C4—Br1	178.49 (13)	O2—S1—C11—C12	40.21 (17)
Br1ⁱ—Br1—C4—C3	70.15 (19)	O3—S1—C11—C12	170.75 (15)
Br1ⁱ—Br1—C4—C5	−110.76 (15)	C1—S1—C11—C12	−72.78 (16)
C3—C4—C5—C6	0.3 (3)	C16—C11—C12—C13	0.8 (3)
Br1—C4—C5—C6	−178.75 (14)	S1—C11—C12—C13	−178.44 (16)
C4—C5—C6—C7	−0.3 (3)	C11—C12—C13—C14	0.5 (3)
C4—C5—C6—C9	178.51 (18)	C12—C13—C14—C15	−1.2 (3)
C8—O1—C7—C6	−178.52 (17)	C12—C13—C14—C17	178.7 (2)
C8—O1—C7—C2	0.69 (19)	C13—C14—C15—C16	0.6 (3)
C5—C6—C7—O1	179.69 (16)	C17—C14—C15—C16	−179.28 (19)
C9—C6—C7—O1	0.9 (3)	C12—C11—C16—C15	−1.3 (3)
C5—C6—C7—C2	0.6 (3)	S1—C11—C16—C15	177.89 (15)
C9—C6—C7—C2	−178.21 (18)	C14—C15—C16—C11	0.6 (3)

Symmetry code: (i) −x+1, −y+2, −z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13···O2ⁱⁱ	0.95	2.54	3.330 (2)	140

Symmetry code: (ii) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13···O2ⁱ	0.95	2.54	3.330 (2)	140.4

Symmetry code: (i) −x+1, −y+1, −z+1.

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. & Lee, U. (2012). Acta Cryst. E68, o3208. CSD CrossRef IUCr Journals Google Scholar
Choi, H. D., Seo, P. J. & Lee, U. (2013). Acta Cryst. E69, o720. CSD CrossRef IUCr Journals Google Scholar
Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2011). Acta Cryst. E67, o1279. Web of Science CSD CrossRef IUCr Journals Google Scholar
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Volume 70| Part 5| May 2014| Page o520

doi:10.1107/S1600536814007181

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