N-(2,5-Dimethoxy­phen­yl)-4-nitro­benzene­sulfonamide

Zhang, G.-Y.; Qian, S.; Li, X.-C.; Wu, Y.

doi:10.1107/S1600536809027962

organic compounds

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ISSN: 2056-9890

Volume 65| Part 8| August 2009| Page o1939

doi:10.1107/S1600536809027962

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N-(2,5-Dimethoxyphenyl)-4-nitrobenzenesulfonamide

Guo-Yao Zhang,^a Shan Qian,^a Xiao-Cen Li ^a and Yong Wu ^a ^*

^aKey Laboratory of Drug Targeting of the Education Ministry, West China School of Pharmacy, Sichuan University, Chengdu 610041, People's Republic of China
^*Correspondence e-mail: wyong@scu.edu.cn

(Received 6 July 2009; accepted 16 July 2009; online 22 July 2009)

The title compound, C₁₄H₁₄N₂O₆S, is an intermediate for the synthesis of β-3-adrenergic receptor agonists. The two methoxy groups are approximately coplanar with the attached benzene ring [C—O—C—C = −2.7 (4) and 9.4 (4)°]. The dihedral angle between the two aromatic rings is 67.16 (12)°. An intramolecular N—H⋯O hydrogen bond is observed. In the crystal, molecules are linked into chains along the c axis by C—H⋯O hydrogen bonds.

Related literature

For biological activity of β-3-adrenergic receptors, see: Bardou et al. (1998 ); Hu et al. (2001 ); Klaus et al. (2001 ); Margareto et al. (2001 ); Ok et al. (2000 ); Parmee et al. (1998 , 2000 ); Tonello et al. (1998 ); Weber et al. (1998 ).

Experimental

Crystal data

C₁₄H₁₄N₂O₆S
M_r = 338.33
Orthorhombic, P b c a
a = 14.532 (4) Å
b = 12.375 (4) Å
c = 17.311 (4) Å
V = 3113.2 (14) Å³
Z = 8
Mo Kα radiation
μ = 0.24 mm⁻¹
T = 292 K
0.48 × 0.44 × 0.42 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: for a sphere (WinGX; Farrugia, 1999 ) T_min = 0.893, T_max = 0.906
4003 measured reflections
2877 independent reflections
1790 reflections with I > 2σ(I)
R_int = 0.004
3 standard reflections every 200 reflections intensity decay: 0.9%

Refinement

R[F² > 2σ(F²)] = 0.040
wR(F²) = 0.121
S = 1.06
2877 reflections
214 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.32 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O2	0.78 (3)	2.20 (3)	2.607 (3)	113 (2)
C8—H8C⋯O4ⁱ	0.96	2.55	3.414 (4)	150
Symmetry code: (i) $[x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: DIFRAC (Gabe & White, 1993 ); cell refinement: DIFRAC; data reduction: NRCVAX (Gabe et al., 1989 ); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809027962/ci2846sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809027962/ci2846Isup2.hkl

checkCIF report

Comment top

The beta 3-adrenergic receptor has been shown to mediate various pharmacological and physiological effects such as lipolysis in white adipocyte tissue, thermogenesis in brown adipocyte tissue (Tonello et al., 1998; Ok et al., 2000; Parmee et al., 1998, 2000) and relaxation of urinary bladder detrusor tissue (Hu et al., 2001; Parmee et al., 1998; Weber et al., 1998). Consequently, several pharmaceutical firms, including ourselves, are engaged in developing potent and selective beta 3-adrenergic receptor agonists for the treatment of obesity, type II diabetes, and frequent urination (Margareto et al., 2001; Bardou et al., 1998; Klaus et al., 2001). In our synthetic work of beta 3-adrenergic receptor agonists, we obtained the title compound. Its crystal structure is reported here.

The two methoxy groups are approximately coplanar with the attached benzene ring [C7—O1—C3—C4 = -2.7 (4)° and C8—O2—C6—C5 9.4 (4)°]. The nitro group is coplanar with the C9-C14 benzene ring. The dihedral angle between the two aromatic rings is 67.16 (12)°. An intramolecular N—H···O hydrogen bond is observed.

The crystal packing of the title compound shows that the molecules are linked by C—H···.O hydrogen bonds (Table 1) to form chains along the c axis.

Related literature top

For biological activity of β-3-adrenergic receptors, see: Bardou et al. (1998); Hu et al. (2001); Klaus et al. (2001); Margareto et al. (2001); Ok et al. (2000); Parmee et al. (1998, 2000); Tonello et al. (1998); Weber et al. (1998).

Experimental top

2,5-Dimethoxybenzenamine (10 mmol) and excess pyridine were dissolved in dichloromethane (20 ml) and a solution of 4-nitrobenzene-1-sulfonyl chloride (13 mmol) in dichloromethane (20 ml) was added dropwise with vigorous stirring at 273 K. After 1 h, the reaction was quenched by addition of water and the oil was washed with diluted HCl. The organic layer separated was evaporated to give the crude product, which was recrystallized from n-hexane -dichloromethane (5:1). Colourless crystals suitable for X-ray analysis were obtained by slow evaporation in n-hexane-dichloromethane at room temperature.

Computing details top

Data collection: DIFRAC (Gabe & White, 1993); cell refinement: DIFRAC (Gabe & White, 1993); data reduction: NRCVAX (Gabe et al., 1989); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound, with displacement ellipsoids drawn at the 50% probability level.
	Fig. 2. A packing diagram for the title compound.

N-(2,5-Dimethoxyphenyl)-4-nitrobenzenesulfonamide top

Crystal data top

C₁₄H₁₄N₂O₆S	F(000) = 1408
M_r = 338.33	D_x = 1.444 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 32 reflections
a = 14.532 (4) Å	θ = 4.3–7.5°
b = 12.375 (4) Å	µ = 0.24 mm⁻¹
c = 17.311 (4) Å	T = 292 K
V = 3113.2 (14) Å³	Block, colourless
Z = 8	0.48 × 0.44 × 0.42 mm

Data collection top

Enraf–Nonius CAD-4 diffractometer	1790 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.004
Graphite monochromator	θ_max = 25.4°, θ_min = 2.4°
ω/2θ scans	h = −17→10
Absorption correction: for a sphere (WinGX; Farrugia, 1999)	k = −2→14
T_min = 0.893, T_max = 0.906	l = −11→20
4003 measured reflections	3 standard reflections every 200 reflections
2877 independent reflections	intensity decay: 0.9%

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)] = 0.040	Hydrogen site location: mixed
wR(F²) = 0.121	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ²(F_o²) + (0.0632P)² + 0.3387P] where P = (F_o² + 2F_c²)/3
2877 reflections	(Δ/σ)_max = 0.001
214 parameters	Δρ_max = 0.20 e Å⁻³
0 restraints	Δρ_min = −0.32 e Å⁻³

Crystal data top

C₁₄H₁₄N₂O₆S	V = 3113.2 (14) Å³
M_r = 338.33	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 14.532 (4) Å	µ = 0.24 mm⁻¹
b = 12.375 (4) Å	T = 292 K
c = 17.311 (4) Å	0.48 × 0.44 × 0.42 mm

Data collection top

Enraf–Nonius CAD-4 diffractometer	1790 reflections with I > 2σ(I)
Absorption correction: for a sphere (WinGX; Farrugia, 1999)	R_int = 0.004
T_min = 0.893, T_max = 0.906	3 standard reflections every 200 reflections
4003 measured reflections	intensity decay: 0.9%
2877 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	0 restraints
wR(F²) = 0.121	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	Δρ_max = 0.20 e Å⁻³
2877 reflections	Δρ_min = −0.32 e Å⁻³
214 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 > 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
S1	0.06666 (4)	0.69183 (6)	0.38224 (3)	0.0473 (2)
N1	0.05816 (14)	0.7151 (2)	0.28983 (13)	0.0530 (6)
H1N	0.0834 (18)	0.669 (2)	0.2672 (16)	0.057 (10)*
N2	−0.23262 (16)	0.3748 (2)	0.44664 (14)	0.0662 (7)
O1	−0.20633 (15)	0.94720 (18)	0.27633 (11)	0.0854 (7)
O2	0.00947 (13)	0.61834 (17)	0.16246 (10)	0.0731 (6)
O3	0.15329 (11)	0.63919 (17)	0.39190 (10)	0.0624 (5)
O4	0.04683 (13)	0.78981 (14)	0.42213 (10)	0.0615 (5)
O5	−0.30528 (13)	0.40717 (19)	0.47199 (13)	0.0831 (7)
O6	−0.21642 (16)	0.28124 (19)	0.43150 (18)	0.1057 (9)
C1	−0.02551 (15)	0.7501 (2)	0.25371 (14)	0.0452 (6)
C2	−0.07889 (17)	0.8326 (2)	0.28188 (15)	0.0549 (7)
H2	−0.0618	0.8681	0.3270	0.066*
C3	−0.15884 (18)	0.8634 (2)	0.24300 (15)	0.0569 (7)
C4	−0.18336 (17)	0.8124 (2)	0.17588 (15)	0.0562 (7)
H4	−0.2366	0.8329	0.1499	0.067*
C5	−0.12900 (19)	0.7305 (2)	0.14695 (15)	0.0576 (7)
H5	−0.1456	0.6966	0.1011	0.069*
C6	−0.04991 (17)	0.6982 (2)	0.18527 (14)	0.0495 (6)
C7	−0.2851 (2)	0.9874 (3)	0.23675 (18)	0.0916 (11)
H7A	−0.2688	1.0047	0.1844	0.137*
H7B	−0.3071	1.0512	0.2623	0.137*
H7C	−0.3325	0.9334	0.2368	0.137*
C8	−0.0013 (2)	0.5726 (3)	0.08822 (16)	0.0856 (11)
H8A	−0.0571	0.5312	0.0866	0.128*
H8B	0.0501	0.5263	0.0772	0.128*
H8C	−0.0041	0.6292	0.0504	0.128*
C9	−0.02178 (15)	0.59843 (19)	0.40462 (12)	0.0392 (5)
C10	−0.00660 (16)	0.4902 (2)	0.39088 (14)	0.0518 (6)
H10	0.0498	0.4670	0.3716	0.062*
C11	−0.07563 (18)	0.4167 (2)	0.40591 (15)	0.0542 (7)
H11	−0.0664	0.3432	0.3978	0.065*
C12	−0.15815 (16)	0.4544 (2)	0.43310 (14)	0.0474 (6)
C13	−0.17421 (17)	0.5610 (2)	0.44706 (15)	0.0536 (7)
H13	−0.2310	0.5838	0.4657	0.064*
C14	−0.10508 (15)	0.6342 (2)	0.43313 (15)	0.0494 (6)
H14	−0.1144	0.7073	0.4428	0.059*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0389 (3)	0.0590 (4)	0.0440 (3)	−0.0088 (3)	−0.0050 (3)	0.0049 (3)
N1	0.0418 (12)	0.0706 (17)	0.0467 (12)	−0.0002 (12)	0.0015 (9)	0.0032 (12)
N2	0.0512 (15)	0.0693 (18)	0.0780 (16)	−0.0135 (13)	−0.0120 (12)	0.0180 (14)
O1	0.0911 (14)	0.0898 (16)	0.0751 (13)	0.0359 (14)	−0.0083 (11)	−0.0015 (12)
O2	0.0859 (14)	0.0786 (14)	0.0547 (12)	0.0178 (12)	−0.0074 (10)	−0.0102 (11)
O3	0.0344 (9)	0.0884 (14)	0.0645 (11)	−0.0040 (9)	−0.0062 (8)	0.0152 (10)
O4	0.0738 (12)	0.0565 (11)	0.0541 (11)	−0.0146 (10)	−0.0101 (9)	−0.0053 (10)
O5	0.0478 (11)	0.0999 (18)	0.1017 (16)	−0.0122 (12)	0.0057 (11)	0.0330 (14)
O6	0.0880 (17)	0.0563 (15)	0.173 (3)	−0.0261 (13)	−0.0048 (17)	0.0040 (16)
C1	0.0409 (12)	0.0526 (14)	0.0422 (12)	−0.0101 (13)	−0.0033 (11)	0.0099 (13)
C2	0.0566 (15)	0.0624 (18)	0.0458 (13)	−0.0020 (14)	−0.0048 (12)	0.0002 (13)
C3	0.0563 (15)	0.0618 (17)	0.0525 (15)	0.0030 (14)	0.0020 (12)	0.0101 (14)
C4	0.0475 (14)	0.0632 (18)	0.0577 (15)	−0.0060 (14)	−0.0077 (12)	0.0131 (15)
C5	0.0602 (17)	0.0620 (18)	0.0505 (15)	−0.0190 (15)	−0.0130 (12)	0.0054 (14)
C6	0.0533 (14)	0.0506 (15)	0.0446 (13)	−0.0061 (13)	0.0019 (11)	0.0057 (13)
C7	0.082 (2)	0.105 (3)	0.088 (2)	0.036 (2)	0.0062 (18)	0.030 (2)
C8	0.128 (3)	0.078 (2)	0.0505 (17)	0.016 (2)	−0.0012 (17)	−0.0066 (17)
C9	0.0350 (12)	0.0436 (13)	0.0389 (12)	0.0026 (11)	−0.0008 (9)	0.0004 (11)
C10	0.0390 (12)	0.0553 (16)	0.0612 (16)	0.0061 (12)	0.0085 (11)	−0.0058 (13)
C11	0.0547 (15)	0.0425 (14)	0.0653 (16)	0.0039 (13)	0.0012 (12)	−0.0019 (13)
C12	0.0391 (13)	0.0484 (15)	0.0548 (14)	−0.0044 (12)	−0.0053 (11)	0.0091 (12)
C13	0.0360 (13)	0.0545 (16)	0.0703 (17)	0.0073 (12)	0.0093 (12)	0.0041 (14)
C14	0.0427 (13)	0.0409 (14)	0.0646 (15)	0.0075 (12)	0.0074 (12)	0.0013 (13)

Geometric parameters (Å, º) top

S1—O4	1.4249 (19)	C4—H4	0.93
S1—O3	1.4273 (18)	C5—C6	1.386 (3)
S1—N1	1.630 (2)	C5—H5	0.93
S1—C9	1.771 (2)	C7—H7A	0.96
N1—C1	1.434 (3)	C7—H7B	0.96
N1—H1N	0.78 (3)	C7—H7C	0.96
N2—O6	1.210 (3)	C8—H8A	0.96
N2—O5	1.212 (3)	C8—H8B	0.96
N2—C12	1.482 (3)	C8—H8C	0.96
O1—C3	1.373 (3)	C9—C10	1.378 (4)
O1—C7	1.424 (3)	C9—C14	1.380 (3)
O2—C6	1.370 (3)	C10—C11	1.379 (3)
O2—C8	1.413 (3)	C10—H10	0.93
C1—C2	1.372 (3)	C11—C12	1.371 (3)
C1—C6	1.393 (3)	C11—H11	0.93
C2—C3	1.396 (3)	C12—C13	1.360 (3)
C2—H2	0.93	C13—C14	1.374 (3)
C3—C4	1.370 (4)	C13—H13	0.93
C4—C5	1.379 (4)	C14—H14	0.93

O4—S1—O3	120.67 (12)	C5—C6—C1	119.0 (2)
O4—S1—N1	108.06 (13)	O1—C7—H7A	109.5
O3—S1—N1	105.22 (11)	O1—C7—H7B	109.5
O4—S1—C9	107.61 (11)	H7A—C7—H7B	109.5
O3—S1—C9	108.45 (11)	O1—C7—H7C	109.5
N1—S1—C9	105.95 (11)	H7A—C7—H7C	109.5
C1—N1—S1	123.06 (17)	H7B—C7—H7C	109.5
C1—N1—H1N	114 (2)	O2—C8—H8A	109.5
S1—N1—H1N	109 (2)	O2—C8—H8B	109.5
O6—N2—O5	124.4 (3)	H8A—C8—H8B	109.5
O6—N2—C12	117.4 (3)	O2—C8—H8C	109.5
O5—N2—C12	118.3 (3)	H8A—C8—H8C	109.5
C3—O1—C7	117.8 (2)	H8B—C8—H8C	109.5
C6—O2—C8	118.8 (2)	C10—C9—C14	120.9 (2)
C2—C1—C6	120.1 (2)	C10—C9—S1	118.70 (18)
C2—C1—N1	123.3 (2)	C14—C9—S1	120.34 (19)
C6—C1—N1	116.6 (2)	C9—C10—C11	119.5 (2)
C1—C2—C3	120.2 (2)	C9—C10—H10	120.3
C1—C2—H2	119.9	C11—C10—H10	120.3
C3—C2—H2	119.9	C12—C11—C10	118.4 (2)
C4—C3—O1	125.0 (2)	C12—C11—H11	120.8
C4—C3—C2	120.0 (3)	C10—C11—H11	120.8
O1—C3—C2	115.0 (2)	C13—C12—C11	122.8 (2)
C3—C4—C5	119.9 (2)	C13—C12—N2	119.4 (2)
C3—C4—H4	120.1	C11—C12—N2	117.8 (2)
C5—C4—H4	120.1	C12—C13—C14	118.9 (2)
C4—C5—C6	120.9 (2)	C12—C13—H13	120.6
C4—C5—H5	119.6	C14—C13—H13	120.6
C6—C5—H5	119.6	C13—C14—C9	119.5 (2)
O2—C6—C5	126.3 (2)	C13—C14—H14	120.3
O2—C6—C1	114.7 (2)	C9—C14—H14	120.3

O4—S1—N1—C1	−61.0 (2)	N1—C1—C6—C5	−178.5 (2)
O3—S1—N1—C1	168.9 (2)	O4—S1—C9—C10	−162.61 (19)
C9—S1—N1—C1	54.1 (2)	O3—S1—C9—C10	−30.5 (2)
S1—N1—C1—C2	47.4 (3)	N1—S1—C9—C10	82.0 (2)
S1—N1—C1—C6	−134.8 (2)	O4—S1—C9—C14	19.3 (2)
C6—C1—C2—C3	1.3 (4)	O3—S1—C9—C14	151.32 (19)
N1—C1—C2—C3	179.0 (2)	N1—S1—C9—C14	−96.1 (2)
C7—O1—C3—C4	−2.7 (4)	C14—C9—C10—C11	−0.1 (4)
C7—O1—C3—C2	175.8 (3)	S1—C9—C10—C11	−178.18 (19)
C1—C2—C3—C4	−1.0 (4)	C9—C10—C11—C12	1.0 (4)
C1—C2—C3—O1	−179.7 (2)	C10—C11—C12—C13	−1.1 (4)
O1—C3—C4—C5	178.6 (2)	C10—C11—C12—N2	178.1 (2)
C2—C3—C4—C5	0.1 (4)	O6—N2—C12—C13	178.0 (3)
C3—C4—C5—C6	0.6 (4)	O5—N2—C12—C13	−2.0 (4)
C8—O2—C6—C5	9.4 (4)	O6—N2—C12—C11	−1.3 (4)
C8—O2—C6—C1	−170.3 (2)	O5—N2—C12—C11	178.7 (2)
C4—C5—C6—O2	−180.0 (2)	C11—C12—C13—C14	0.2 (4)
C4—C5—C6—C1	−0.3 (4)	N2—C12—C13—C14	−179.0 (2)
C2—C1—C6—O2	179.1 (2)	C12—C13—C14—C9	0.7 (4)
N1—C1—C6—O2	1.2 (3)	C10—C9—C14—C13	−0.8 (4)
C2—C1—C6—C5	−0.7 (4)	S1—C9—C14—C13	177.25 (19)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O2	0.78 (3)	2.20 (3)	2.607 (3)	113 (2)
C8—H8C···O4ⁱ	0.96	2.55	3.414 (4)	150

Symmetry code: (i) x, −y+3/2, z−1/2.

Experimental details

Crystal data
Chemical formula	C₁₄H₁₄N₂O₆S
M_r	338.33
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	292
a, b, c (Å)	14.532 (4), 12.375 (4), 17.311 (4)
V (Å³)	3113.2 (14)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.24
Crystal size (mm)	0.48 × 0.44 × 0.42

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	For a sphere (WinGX; Farrugia, 1999)
T_min, T_max	0.893, 0.906
No. of measured, independent and observed [I > 2σ(I)] reflections	4003, 2877, 1790
R_int	0.004
(sin θ/λ)_max (Å⁻¹)	0.604

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.121, 1.06
No. of reflections	2877
No. of parameters	214
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.20, −0.32

Computer programs: DIFRAC (Gabe & White, 1993), NRCVAX (Gabe et al., 1989), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O2	0.78 (3)	2.20 (3)	2.607 (3)	113 (2)
C8—H8C···O4ⁱ	0.96	2.55	3.414 (4)	150

Symmetry code: (i) x, −y+3/2, z−1/2.

References

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Volume 65| Part 8| August 2009| Page o1939

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