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

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

doi:10.1107/S1600536814008149

organic compounds

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ISSN: 2056-9890

Volume 70| Part 5| May 2014| Page o567

doi:10.1107/S1600536814008149

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5-Bromo-2,7-dimethyl-3-(3-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 27 March 2014; accepted 11 April 2014; online 16 April 2014)

In the title compound, C₁₇H₁₅BrO₃S, the dihedral angle between the mean planes of the benzofuran and 3-methylphenyl rings is 77.37 (5)°. In the crystal, molecules are linked via pairs of Br⋯O [Br⋯O = 3.335 (2) Å] contacts into inversion dimers. These dimers are further linked by C—H⋯O hydrogen bonds and π–π interactions between the benzene and furan rings of neighbouring molecules [centroid–centroid separation = 3.884 (3) Å] into supramolecular chains running along the a-axis direction.

CCDC reference: 996711

Related literature

For background information and the crystal structures of related compounds, see: Choi et al. (2011 , 2012 , 2013 ). For a review of halogen bonding, see: Politzer et al. (2007 ).

Experimental

Crystal data

C₁₇H₁₅BrO₃S
M_r = 379.26
Monoclinic, P 2₁ /c
a = 8.8813 (3) Å
b = 6.5976 (2) Å
c = 26.5044 (8) Å
β = 97.635 (1)°
V = 1539.26 (8) Å³
Z = 4
Mo Kα radiation
μ = 2.82 mm⁻¹
T = 296 K
0.50 × 0.46 × 0.15 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.379, T_max = 0.746
26392 measured reflections
3831 independent reflections
3188 reflections with I > 2σ(I)
R_int = 0.043

Refinement

R[F² > 2σ(F²)] = 0.031
wR(F²) = 0.081
S = 1.07
3831 reflections
202 parameters
H-atom parameters constrained
Δρ_max = 0.56 e Å⁻³
Δρ_min = −0.45 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C10—H10B⋯O2ⁱ	0.96	2.54	3.338 (3)	141
C17—H17C⋯O3ⁱⁱ	0.96	2.41	3.357 (3)	170
Symmetry codes: (i) x, y-1, z; (ii) 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 for Windows (Farrugia, 2012 ) and DIAMOND (Brandenburg, 1998 ); software used to prepare material for publication: SHELXL97.

Supporting information

CCDC reference: 996711

Crystal structure: contains datablock I. DOI: 10.1107/S1600536814008149/bh2497sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814008149/bh2497Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536814008149/bh2497Isup3.cml

checkCIF report

Experimental top

Synthesis and crystallization 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-(3-methylphenylsulfanyl)-1-benzofuran (312 mg, 0.9 mmol) in dichloromethane (40 mL) at 273 K. After being stirred at room temperature for 8 h., 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 68%, m.p. 438–439 K; R_f = 0.51 (hexane–ethyl acetate, 4:1 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.

Refinement top

Crystal data, data collection and structure refinement details are summarized in Table 1. All H atoms were positioned geometrically and refined using a riding model, with C—H = 0.95 Å for aryl and 0.98 Å for methyl H atoms, respectively. U_iso (H) = 1.2U_eq (C) for aryl and 1.5U_eq (C) for methyl H atoms. The positions of methyl hydrogens were optimized using the SHELXL-97's command AFIX 137 (Sheldrick, 2008).

Results and discussion 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 0.010 (2) Å from the least-squares plane defined by the nine constituent atoms. The 3-methylphenyl ring is essentially planar, with a mean deviation of 0.004 (1) Å from the least-squares plane defined by the six constituent atoms. The dihedral angle formed by the benzofuran ring system and the 3-methylphenyl ring is 77.37 (5)°. In the crystal structure (Fig. 2), molecules are linked by pairs of Br···O halogen-bondings (Politzer et al. 2007) between the bromine and the O atom of the O═S═O unit [Br1···O2ⁱⁱⁱ = 3.335 (2) Å, C4—Br1···O2ⁱⁱⁱ = 168.67 (6)°, symmetry code: (iii) -x+1, -y+2, -z+1]. These dimers are further linked by C—H···O hydrogen bonds (Table 1), and by π···π interactions between the benzene and furan rings of neighbouring molecules, with a Cg1···Cg2^iv distance of 3.884 (3) Å and an interplanar distance of 3.440 (3) Å resulting in a slippage of 1.804 (3) Å (Cg1 and Cg2 are the centroids of the C2–C7 benzene ring and the C1/C2/C7/O1/C8 furan ring, respectively), forming supramolecular chains running along the a–axis direction.

Related literature top

For background information and the crystal structures of related compounds, see: Choi et al. (2011, 2012, 2013). For a review of halogen bonding, see: Politzer et al. (2007).

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, Br···O and π···π 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, y - 1, z; (ii) x + 1, y, z; (iii) - x + 1, - y + 2, - z + 1; (iv) - x, - y + 1, - z + 1.]

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

Crystal data top

C₁₇H₁₅BrO₃S	F(000) = 768
M_r = 379.26	D_x = 1.637 Mg m⁻³
Monoclinic, P2₁/c	Melting point = 439–438 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 8.8813 (3) Å	Cell parameters from 9774 reflections
b = 6.5976 (2) Å	θ = 2.3–28.2°
c = 26.5044 (8) Å	µ = 2.82 mm⁻¹
β = 97.635 (1)°	T = 296 K
V = 1539.26 (8) Å³	Block, colourless
Z = 4	0.50 × 0.46 × 0.15 mm

Data collection top

Bruker SMART APEXII CCD diffractometer	3831 independent reflections
Radiation source: rotating anode	3188 reflections with I > 2σ(I)
Graphite multilayer monochromator	R_int = 0.043
Detector resolution: 10.0 pixels mm^-1	θ_max = 28.3°, θ_min = 1.6°
ϕ and ω scans	h = −11→11
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −8→8
T_min = 0.379, T_max = 0.746	l = −35→35
26392 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: difference Fourier map
wR(F²) = 0.081	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.0364P)² + 0.7777P] where P = (F_o² + 2F_c²)/3
3831 reflections	(Δ/σ)_max = 0.002
202 parameters	Δρ_max = 0.56 e Å⁻³
0 restraints	Δρ_min = −0.45 e Å⁻³

Crystal data top

C₁₇H₁₅BrO₃S	V = 1539.26 (8) Å³
M_r = 379.26	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 8.8813 (3) Å	µ = 2.82 mm⁻¹
b = 6.5976 (2) Å	T = 296 K
c = 26.5044 (8) Å	0.50 × 0.46 × 0.15 mm
β = 97.635 (1)°

Data collection top

Bruker SMART APEXII CCD diffractometer	3831 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	3188 reflections with I > 2σ(I)
T_min = 0.379, T_max = 0.746	R_int = 0.043
26392 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.031	0 restraints
wR(F²) = 0.081	H-atom parameters constrained
S = 1.07	Δρ_max = 0.56 e Å⁻³
3831 reflections	Δρ_min = −0.45 e Å⁻³
202 parameters

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

	x	y	z	U_iso*/U_eq
Br1	0.46068 (3)	0.80654 (4)	0.428686 (8)	0.04118 (9)
S1	0.26202 (5)	0.72154 (8)	0.641971 (18)	0.02783 (11)
O1	0.09711 (16)	0.2852 (2)	0.55049 (5)	0.0314 (3)
O2	0.27849 (16)	0.9169 (2)	0.61959 (5)	0.0352 (3)
O3	0.16243 (16)	0.7009 (3)	0.68033 (6)	0.0380 (4)
C1	0.2041 (2)	0.5514 (3)	0.59334 (7)	0.0284 (4)
C2	0.2454 (2)	0.5613 (3)	0.54261 (7)	0.0277 (4)
C3	0.3313 (2)	0.6908 (3)	0.51640 (7)	0.0305 (4)
H3	0.3777	0.8062	0.5314	0.037*
C4	0.3435 (2)	0.6375 (4)	0.46673 (7)	0.0318 (4)
C5	0.2756 (2)	0.4660 (4)	0.44286 (7)	0.0347 (5)
H5	0.2888	0.4380	0.4093	0.042*
C6	0.1884 (2)	0.3360 (3)	0.46849 (8)	0.0325 (4)
C7	0.1763 (2)	0.3932 (3)	0.51806 (7)	0.0291 (4)
C8	0.1157 (2)	0.3850 (3)	0.59611 (7)	0.0302 (4)
C9	0.1153 (3)	0.1474 (4)	0.44553 (8)	0.0415 (5)
H9A	0.1709	0.0312	0.4596	0.062*
H9B	0.1157	0.1499	0.4093	0.062*
H9C	0.0125	0.1399	0.4529	0.062*
C10	0.0370 (3)	0.2911 (3)	0.63612 (9)	0.0368 (5)
H10A	0.0463	0.3777	0.6655	0.055*
H10B	0.0821	0.1619	0.6454	0.055*
H10C	−0.0685	0.2730	0.6235	0.055*
C11	0.4444 (2)	0.6401 (3)	0.66941 (7)	0.0283 (4)
C12	0.5609 (2)	0.7803 (3)	0.67428 (7)	0.0314 (4)
H12	0.5452	0.9090	0.6603	0.038*
C13	0.7026 (2)	0.7273 (4)	0.70039 (8)	0.0389 (5)
C14	0.7213 (3)	0.5329 (4)	0.71966 (8)	0.0461 (6)
H14	0.8152	0.4950	0.7369	0.055*
C15	0.6045 (3)	0.3937 (4)	0.71410 (8)	0.0444 (6)
H15	0.6208	0.2638	0.7274	0.053*
C16	0.4631 (2)	0.4458 (4)	0.68888 (8)	0.0367 (5)
H16	0.3834	0.3533	0.6852	0.044*
C17	0.8290 (2)	0.8819 (5)	0.70728 (10)	0.0535 (7)
H17A	0.8362	0.9388	0.7409	0.080*
H17B	0.8078	0.9877	0.6825	0.080*
H17C	0.9233	0.8176	0.7029	0.080*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.04301 (14)	0.04977 (17)	0.03230 (13)	0.01099 (10)	0.01067 (9)	0.00424 (9)
S1	0.0264 (2)	0.0325 (3)	0.0236 (2)	0.00823 (19)	−0.00028 (17)	−0.00524 (18)
O1	0.0345 (7)	0.0306 (8)	0.0276 (7)	0.0047 (6)	−0.0014 (6)	−0.0037 (6)
O2	0.0379 (7)	0.0294 (8)	0.0352 (8)	0.0090 (6)	−0.0061 (6)	−0.0033 (6)
O3	0.0309 (7)	0.0511 (11)	0.0329 (8)	0.0049 (7)	0.0072 (6)	−0.0131 (7)
C1	0.0293 (9)	0.0319 (11)	0.0229 (9)	0.0079 (8)	−0.0007 (7)	−0.0030 (7)
C2	0.0272 (9)	0.0315 (11)	0.0228 (9)	0.0105 (8)	−0.0028 (7)	−0.0035 (7)
C3	0.0295 (9)	0.0333 (12)	0.0276 (9)	0.0086 (8)	−0.0002 (7)	−0.0019 (8)
C4	0.0314 (9)	0.0382 (12)	0.0255 (9)	0.0132 (8)	0.0027 (7)	0.0025 (8)
C5	0.0359 (10)	0.0439 (13)	0.0230 (9)	0.0166 (9)	−0.0016 (8)	−0.0055 (8)
C6	0.0328 (10)	0.0336 (12)	0.0288 (10)	0.0137 (8)	−0.0049 (8)	−0.0061 (8)
C7	0.0295 (9)	0.0304 (11)	0.0253 (9)	0.0100 (8)	−0.0033 (7)	−0.0012 (8)
C8	0.0317 (9)	0.0304 (11)	0.0271 (9)	0.0100 (8)	−0.0012 (7)	−0.0028 (8)
C9	0.0484 (12)	0.0394 (13)	0.0332 (11)	0.0111 (10)	−0.0072 (9)	−0.0118 (9)
C10	0.0409 (11)	0.0353 (13)	0.0343 (11)	0.0029 (9)	0.0052 (9)	−0.0013 (9)
C11	0.0283 (9)	0.0390 (11)	0.0174 (8)	0.0115 (8)	0.0025 (7)	−0.0011 (7)
C12	0.0287 (9)	0.0419 (13)	0.0239 (9)	0.0067 (8)	0.0044 (7)	−0.0019 (8)
C13	0.0285 (10)	0.0651 (16)	0.0235 (9)	0.0108 (10)	0.0057 (8)	−0.0055 (10)
C14	0.0348 (11)	0.0774 (19)	0.0253 (10)	0.0247 (12)	0.0005 (8)	0.0031 (11)
C15	0.0542 (13)	0.0508 (15)	0.0275 (10)	0.0248 (12)	0.0033 (10)	0.0101 (10)
C16	0.0405 (11)	0.0430 (13)	0.0266 (9)	0.0113 (9)	0.0050 (8)	0.0036 (9)
C17	0.0263 (10)	0.086 (2)	0.0482 (14)	0.0016 (12)	0.0042 (9)	−0.0118 (14)

Geometric parameters (Å, º) top

Br1—C4	1.903 (2)	C9—H9A	0.9600
Br1—O2ⁱ	3.3350 (16)	C9—H9B	0.9600
S1—O2	1.4341 (17)	C9—H9C	0.9600
S1—O3	1.4400 (15)	C10—H10A	0.9600
S1—C1	1.735 (2)	C10—H10B	0.9600
S1—C11	1.7687 (19)	C10—H10C	0.9600
O1—C8	1.368 (2)	C11—C12	1.381 (3)
O1—C7	1.379 (3)	C11—C16	1.383 (3)
C1—C8	1.358 (3)	C12—C13	1.398 (3)
C1—C2	1.441 (3)	C12—H12	0.9300
C2—C7	1.387 (3)	C13—C14	1.382 (4)
C2—C3	1.391 (3)	C13—C17	1.510 (4)
C3—C4	1.381 (3)	C14—C15	1.379 (4)
C3—H3	0.9300	C14—H14	0.9300
C4—C5	1.394 (3)	C15—C16	1.385 (3)
C5—C6	1.392 (3)	C15—H15	0.9300
C5—H5	0.9300	C16—H16	0.9300
C6—C7	1.385 (3)	C17—H17A	0.9600
C6—C9	1.495 (3)	C17—H17B	0.9600
C8—C10	1.481 (3)	C17—H17C	0.9600

C4—Br1—O2ⁱ	168.67 (6)	H9A—C9—H9B	109.5
O2—S1—O3	118.89 (9)	C6—C9—H9C	109.5
O2—S1—C1	108.10 (9)	H9A—C9—H9C	109.5
O3—S1—C1	108.30 (10)	H9B—C9—H9C	109.5
O2—S1—C11	107.76 (10)	C8—C10—H10A	109.5
O3—S1—C11	107.20 (9)	C8—C10—H10B	109.5
C1—S1—C11	105.88 (9)	H10A—C10—H10B	109.5
C8—O1—C7	106.91 (16)	C8—C10—H10C	109.5
C8—C1—C2	107.93 (17)	H10A—C10—H10C	109.5
C8—C1—S1	126.84 (15)	H10B—C10—H10C	109.5
C2—C1—S1	125.22 (16)	C12—C11—C16	122.29 (19)
C7—C2—C3	119.64 (18)	C12—C11—S1	117.95 (16)
C7—C2—C1	104.47 (18)	C16—C11—S1	119.54 (17)
C3—C2—C1	135.88 (19)	C11—C12—C13	119.5 (2)
C4—C3—C2	115.9 (2)	C11—C12—H12	120.2
C4—C3—H3	122.0	C13—C12—H12	120.2
C2—C3—H3	122.0	C14—C13—C12	118.1 (2)
C3—C4—C5	123.7 (2)	C14—C13—C17	122.1 (2)
C3—C4—Br1	118.26 (17)	C12—C13—C17	119.8 (2)
C5—C4—Br1	117.99 (15)	C15—C14—C13	121.8 (2)
C6—C5—C4	120.94 (18)	C15—C14—H14	119.1
C6—C5—H5	119.5	C13—C14—H14	119.1
C4—C5—H5	119.5	C14—C15—C16	120.5 (2)
C7—C6—C5	114.4 (2)	C14—C15—H15	119.8
C7—C6—C9	122.0 (2)	C16—C15—H15	119.8
C5—C6—C9	123.63 (19)	C11—C16—C15	117.8 (2)
O1—C7—C6	124.08 (19)	C11—C16—H16	121.1
O1—C7—C2	110.57 (16)	C15—C16—H16	121.1
C6—C7—C2	125.3 (2)	C13—C17—H17A	109.5
C1—C8—O1	110.12 (17)	C13—C17—H17B	109.5
C1—C8—C10	135.10 (19)	H17A—C17—H17B	109.5
O1—C8—C10	114.78 (19)	C13—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	−149.32 (17)	C3—C2—C7—O1	179.96 (16)
O3—S1—C1—C8	−19.3 (2)	C1—C2—C7—O1	0.1 (2)
C11—S1—C1—C8	95.42 (18)	C3—C2—C7—C6	2.0 (3)
O2—S1—C1—C2	32.05 (18)	C1—C2—C7—C6	−177.80 (18)
O3—S1—C1—C2	162.10 (16)	C2—C1—C8—O1	0.2 (2)
C11—S1—C1—C2	−83.20 (18)	S1—C1—C8—O1	−178.57 (14)
C8—C1—C2—C7	−0.2 (2)	C2—C1—C8—C10	−179.5 (2)
S1—C1—C2—C7	178.62 (14)	S1—C1—C8—C10	1.7 (3)
C8—C1—C2—C3	180.0 (2)	C7—O1—C8—C1	−0.2 (2)
S1—C1—C2—C3	−1.2 (3)	C7—O1—C8—C10	179.60 (16)
C7—C2—C3—C4	−1.2 (3)	O2—S1—C11—C12	12.15 (17)
C1—C2—C3—C4	178.6 (2)	O3—S1—C11—C12	−116.91 (15)
C2—C3—C4—C5	0.1 (3)	C1—S1—C11—C12	127.64 (16)
C2—C3—C4—Br1	−179.53 (13)	O2—S1—C11—C16	−173.10 (15)
O2ⁱ—Br1—C4—C3	58.1 (4)	O3—S1—C11—C16	57.84 (18)
O2ⁱ—Br1—C4—C5	−121.5 (3)	C1—S1—C11—C16	−57.62 (18)
C3—C4—C5—C6	0.4 (3)	C16—C11—C12—C13	−1.1 (3)
Br1—C4—C5—C6	−179.97 (15)	S1—C11—C12—C13	173.54 (15)
C4—C5—C6—C7	0.2 (3)	C11—C12—C13—C14	1.2 (3)
C4—C5—C6—C9	−178.61 (19)	C11—C12—C13—C17	−178.06 (19)
C8—O1—C7—C6	177.97 (18)	C12—C13—C14—C15	−0.6 (3)
C8—O1—C7—C2	0.0 (2)	C17—C13—C14—C15	178.7 (2)
C5—C6—C7—O1	−179.12 (17)	C13—C14—C15—C16	−0.3 (3)
C9—C6—C7—O1	−0.3 (3)	C12—C11—C16—C15	0.2 (3)
C5—C6—C7—C2	−1.5 (3)	S1—C11—C16—C15	−174.34 (15)
C9—C6—C7—C2	177.39 (19)	C14—C15—C16—C11	0.5 (3)

Symmetry code: (i) −x+1, −y+2, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10B···O2ⁱⁱ	0.96	2.54	3.338 (3)	141
C17—H17C···O3ⁱⁱⁱ	0.96	2.41	3.357 (3)	170

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10B···O2ⁱ	0.96	2.54	3.338 (3)	140.9
C17—H17C···O3ⁱⁱ	0.96	2.41	3.357 (3)	169.8

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

References

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Volume 70| Part 5| May 2014| Page o567

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