(E)-4-Amino-N-(1,2-dihydro­pyridin-2-yl­idene)benzene­sulfonamide nitro­methane monosolvate

Ghorab, M.M.; Al-Said, M.S.; Ghabbour, H.A.; Chantrapromma, S.; Fun, H.-K.

doi:10.1107/S1600536812009865

organic compounds

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ISSN: 2056-9890

Volume 68| Part 4| April 2012| Page o1030

doi:10.1107/S1600536812009865

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(E)-4-Amino-N-(1,2-dihydropyridin-2-ylidene)benzenesulfonamide nitromethane monosolvate

Mostafa M. Ghorab,^a Mansour S. Al-Said,^a Hazem A. Ghabbour,^b Suchada Chantrapromma ^c ‡ and Hoong-Kun Fun ^d ^*§

^aMedicinal, Aromatic and Poisonous Plants Research Center (MAPPRC), College of Pharmacy, King Saud University, PO Box 2457, Riyadh 11451, Saudi Arabia, ^bDepartment of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, PO Box 2457, Riyadh 11451, Saudi Arabia, ^cCrystal Materials Research Unit, Department of Chemistry, Faculty of Science, Prince of Songkla University, Hat-Yai, Songkhla 90112, Thailand, and ^dX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
^*Correspondence e-mail: hkfun@usm.my

(Received 27 February 2012; accepted 6 March 2012; online 10 March 2012)

In the title solvate, C₁₁H₁₁N₃O₂S·CH₃NO₂, the dihedral angle between the benzene ring and the N-containing ring is 85.94 (11)°, and an approximate V shape arises for the sulfonamide molecule. In the crystal, N—H⋯O and N—H⋯N hydrogen bonds and weak C—H⋯O interactions link the sulfonamide molecules into a three-dimensional network. The nitromethane solvent molecules are located in the interstitial sites in the sulfonamide network.

Related literature

For background to the applications of sulfonamide compounds, see: Ghorab et al. (2009 );

Experimental

Crystal data

C₁₁H₁₁N₃O₂S·CH₃NO₂
M_r = 310.34
Orthorhombic, P b c a
a = 10.5179 (3) Å
b = 12.4857 (3) Å
c = 22.7237 (6) Å
V = 2984.15 (14) Å³
Z = 8
Cu Kα radiation
μ = 2.14 mm⁻¹
T = 296 K
0.54 × 0.43 × 0.31 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.392, T_max = 0.554
14569 measured reflections
2799 independent reflections
2386 reflections with I > 2σ(I)
R_int = 0.062

Refinement

R[F² > 2σ(F²)] = 0.045
wR(F²) = 0.144
S = 1.07
2799 reflections
196 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.25 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
N2—H1N2⋯O2ⁱ	0.87	2.10	2.971 (3)	174
N2—H2N2⋯O1ⁱⁱ	0.87	2.34	3.162 (3)	157
N3—H1N3⋯N1ⁱⁱⁱ	0.86 (2)	2.09 (2)	2.948 (2)	178 (2)
C8—H8A⋯O1ⁱⁱⁱ	0.93	2.52	3.160 (3)	126
Symmetry codes: (i) $[-x, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[-x-{\script{1\over 2}}, y-{\script{1\over 2}}, z]$ ; (iii) -x, -y+1, -z.

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812009865/hb6660sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812009865/hb6660Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812009865/hb6660Isup3.cml

checkCIF report

Comment top

As part of our ongoing studies of sulfonamides with potential biological activities (Ghorab et al. (2009), the present investigation deals with the synthesis of the title compound, (I), (Fig. 1) a sulfonamide bearing a pyridine moiety to be evaluated as anticancer agent.

The environment of S atom is distorted tetrahedral geometry [angles around S atom are 104.49 (9) - 115.82 (10)°] with two O atoms, one N atom of the amide group and one C atom of the benzene ring. The dihedral angle between the benzene ring and the N atom-containing ring is 85.94 (11)°. The amino group is co-planar with its bound benzene ring with r.m.s. 0.0126 (2) Å for the seven non H atoms (C1–C6/N2).

In the crystal (Fig. 2), the molecules of sulfonamide derivative are linked by N—H···O and N—H···N hydrogen bonds and weak C···H···O interactions (Table 1) into a three dimensional network. The nitromethane solvent molecules are located in the interstitial sites of the sulfonamide network.

Related literature top

For background to the applications of sulfonamide compounds, see: Ghorab et al. (2009);

Experimental top

A mixture of (E)-3-(dimethylamino)-1-(thiophen-2-yl)prop-2-en-1-one (1.81 g, 0.01 mole) and sulfapyridine (2.49 g, 0.01 mole) in absolute ethanol (30 ml) was heated under reflux for 12 hr. The reaction mixture was filtered and pink blocks of (I) were obtained by the slow evaporation of an ethanol/nitromethane (3:1) solution at room temperature.

Structure description top

For background to the applications of sulfonamide compounds, see: Ghorab et al. (2009);

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The structure of (I), showing 30% probability displacement ellipsoids.
	Fig. 2. The crystal packing of (I) viewed along the a axis, showing three dimensional network.

(E)-4-Amino-N-(1,2-dihydropyridin-2-ylidene)benzenesulfonamide nitromethane monosolvate top

Crystal data top

C₁₁H₁₁N₃O₂S·CH₃NO₂	F(000) = 1296
M_r = 310.34	D_x = 1.381 Mg m⁻³
Orthorhombic, Pbca	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 2799 reflections
a = 10.5179 (3) Å	θ = 5.7–71.6°
b = 12.4857 (3) Å	µ = 2.14 mm⁻¹
c = 22.7237 (6) Å	T = 296 K
V = 2984.15 (14) Å³	Block, pink
Z = 8	0.54 × 0.43 × 0.31 mm

Data collection top

Bruker SMART APEXII CCD diffractometer	2799 independent reflections
Radiation source: fine-focus sealed tube	2386 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.062
φ and ω scans	θ_max = 71.6°, θ_min = 5.7°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −11→10
T_min = 0.392, T_max = 0.554	k = −15→15
14569 measured reflections	l = −27→27

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.045	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.144	w = 1/[σ²(F_o²) + (0.0843P)² + 0.5181P] where P = (F_o² + 2F_c²)/3
S = 1.07	(Δ/σ)_max = 0.001
2799 reflections	Δρ_max = 0.25 e Å⁻³
196 parameters	Δρ_min = −0.42 e Å⁻³
0 restraints	Extinction correction: SHELXTL (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0022 (3)

Crystal data top

C₁₁H₁₁N₃O₂S·CH₃NO₂	V = 2984.15 (14) Å³
M_r = 310.34	Z = 8
Orthorhombic, Pbca	Cu Kα radiation
a = 10.5179 (3) Å	µ = 2.14 mm⁻¹
b = 12.4857 (3) Å	T = 296 K
c = 22.7237 (6) Å	0.54 × 0.43 × 0.31 mm

Data collection top

Bruker SMART APEXII CCD diffractometer	2799 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	2386 reflections with I > 2σ(I)
T_min = 0.392, T_max = 0.554	R_int = 0.062
14569 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	0 restraints
wR(F²) = 0.144	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	Δρ_max = 0.25 e Å⁻³
2799 reflections	Δρ_min = −0.42 e Å⁻³
196 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
S1	0.03202 (5)	0.52678 (4)	0.13912 (2)	0.0537 (2)
O1	−0.04470 (16)	0.62229 (11)	0.13586 (7)	0.0664 (4)
O2	0.14832 (16)	0.53613 (12)	0.17203 (7)	0.0696 (4)
N1	0.05275 (16)	0.49231 (13)	0.07212 (8)	0.0549 (4)
N2	−0.27661 (19)	0.18108 (17)	0.24298 (10)	0.0806 (6)
H1N2	−0.2408	0.1417	0.2699	0.097*
H2N2	−0.3364	0.1534	0.2213	0.097*
N3	0.13565 (17)	0.39072 (14)	−0.00078 (8)	0.0587 (4)
H1N3	0.082 (2)	0.4266 (17)	−0.0216 (10)	0.054 (6)*
C1	−0.05963 (18)	0.42658 (14)	0.17206 (8)	0.0499 (4)
C2	−0.1786 (2)	0.40208 (16)	0.14851 (9)	0.0547 (5)
H2A	−0.2093	0.4405	0.1165	0.066*
C3	−0.2504 (2)	0.32171 (17)	0.17237 (9)	0.0576 (5)
H3A	−0.3299	0.3063	0.1565	0.069*
C4	−0.20549 (19)	0.26212 (16)	0.22053 (9)	0.0567 (5)
C5	−0.0891 (2)	0.29027 (18)	0.24482 (9)	0.0628 (5)
H5A	−0.0599	0.2542	0.2780	0.075*
C6	−0.0163 (2)	0.37042 (17)	0.22084 (9)	0.0576 (5)
H6A	0.0623	0.3871	0.2373	0.069*
C7	0.13465 (18)	0.41433 (15)	0.05728 (9)	0.0530 (4)
C8	0.2136 (2)	0.3168 (2)	−0.02582 (12)	0.0741 (6)
H8A	0.2104	0.3049	−0.0662	0.089*
C9	0.2955 (3)	0.2609 (2)	0.00786 (14)	0.0855 (8)
H9A	0.3498	0.2106	−0.0088	0.103*
C10	0.2968 (3)	0.2799 (2)	0.06752 (14)	0.0857 (8)
H10A	0.3523	0.2413	0.0913	0.103*
C11	0.2185 (2)	0.35419 (18)	0.09265 (11)	0.0708 (6)
H11A	0.2205	0.3651	0.1331	0.085*
O3	0.0798 (3)	0.0856 (2)	0.04675 (11)	0.1239 (9)
O4	−0.0699 (2)	−0.0317 (2)	0.06434 (11)	0.1120 (8)
N4	0.0045 (3)	0.0378 (3)	0.08153 (15)	0.1093 (9)
C12	0.0102 (4)	0.0684 (4)	0.14512 (17)	0.1265 (14)
H12A	−0.0722	0.0921	0.1578	0.190*
H12B	0.0706	0.1253	0.1503	0.190*
H12C	0.0358	0.0076	0.1681	0.190*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0566 (4)	0.0492 (3)	0.0551 (3)	−0.00291 (18)	−0.00473 (19)	−0.00030 (17)
O1	0.0793 (11)	0.0487 (8)	0.0712 (10)	0.0061 (7)	0.0029 (7)	0.0001 (6)
O2	0.0653 (10)	0.0710 (9)	0.0724 (10)	−0.0133 (7)	−0.0152 (8)	−0.0063 (7)
N1	0.0541 (9)	0.0559 (8)	0.0546 (9)	0.0045 (7)	−0.0008 (7)	0.0066 (7)
N2	0.0624 (12)	0.0869 (13)	0.0923 (15)	−0.0077 (10)	−0.0068 (10)	0.0371 (11)
N3	0.0544 (10)	0.0631 (9)	0.0587 (10)	0.0083 (8)	−0.0006 (8)	0.0047 (8)
C1	0.0513 (10)	0.0518 (9)	0.0464 (9)	0.0002 (8)	−0.0059 (7)	−0.0004 (7)
C2	0.0549 (11)	0.0588 (10)	0.0505 (10)	0.0017 (8)	−0.0082 (8)	0.0071 (8)
C3	0.0479 (10)	0.0659 (11)	0.0589 (11)	−0.0003 (8)	−0.0077 (8)	0.0038 (9)
C4	0.0494 (10)	0.0626 (10)	0.0580 (11)	0.0039 (9)	0.0040 (8)	0.0082 (8)
C5	0.0618 (13)	0.0740 (12)	0.0525 (10)	0.0043 (10)	−0.0075 (9)	0.0153 (9)
C6	0.0546 (11)	0.0663 (11)	0.0518 (11)	−0.0017 (9)	−0.0110 (8)	0.0050 (8)
C7	0.0476 (10)	0.0520 (9)	0.0595 (11)	−0.0021 (8)	−0.0016 (8)	0.0072 (8)
C8	0.0688 (14)	0.0791 (14)	0.0744 (14)	0.0156 (12)	0.0052 (11)	−0.0043 (11)
C9	0.0784 (17)	0.0795 (15)	0.0985 (19)	0.0293 (14)	0.0006 (14)	−0.0035 (14)
C10	0.0832 (17)	0.0737 (14)	0.100 (2)	0.0258 (13)	−0.0213 (15)	0.0060 (13)
C11	0.0739 (15)	0.0672 (12)	0.0712 (14)	0.0110 (11)	−0.0150 (11)	0.0046 (10)
O3	0.1205 (18)	0.148 (2)	0.1029 (17)	−0.0638 (17)	0.0212 (14)	−0.0115 (15)
O4	0.0996 (15)	0.141 (2)	0.0955 (15)	−0.0502 (15)	0.0236 (13)	−0.0211 (13)
N4	0.0867 (17)	0.139 (2)	0.103 (2)	−0.0042 (17)	0.0109 (16)	−0.0112 (17)
C12	0.122 (3)	0.169 (4)	0.089 (2)	−0.013 (3)	0.004 (2)	−0.033 (2)

Geometric parameters (Å, º) top

S1—O2	1.4384 (16)	C5—C6	1.373 (3)
S1—O1	1.4418 (15)	C5—H5A	0.9300
S1—N1	1.5971 (18)	C6—H6A	0.9300
S1—C1	1.7477 (19)	C7—C11	1.410 (3)
N1—C7	1.343 (3)	C8—C9	1.347 (4)
N2—C4	1.358 (3)	C8—H8A	0.9300
N2—H1N2	0.8700	C9—C10	1.377 (4)
N2—H2N2	0.8699	C9—H9A	0.9300
N3—C7	1.352 (3)	C10—C11	1.365 (4)
N3—C8	1.359 (3)	C10—H10A	0.9300
N3—H1N3	0.86 (2)	C11—H11A	0.9300
C1—C6	1.389 (3)	O3—N4	1.268 (4)
C1—C2	1.395 (3)	O4—N4	1.232 (4)
C2—C3	1.368 (3)	N4—C12	1.496 (5)
C2—H2A	0.9300	C12—H12A	0.9600
C3—C4	1.405 (3)	C12—H12B	0.9600
C3—H3A	0.9300	C12—H12C	0.9600
C4—C5	1.388 (3)

O2—S1—O1	115.82 (10)	C5—C6—C1	120.10 (19)
O2—S1—N1	113.66 (10)	C5—C6—H6A	119.9
O1—S1—N1	104.49 (9)	C1—C6—H6A	119.9
O2—S1—C1	107.73 (10)	N1—C7—N3	114.09 (17)
O1—S1—C1	107.78 (9)	N1—C7—C11	130.1 (2)
N1—S1—C1	106.90 (9)	N3—C7—C11	115.81 (19)
C7—N1—S1	121.49 (14)	C9—C8—N3	120.0 (2)
C4—N2—H1N2	116.5	C9—C8—H8A	120.0
C4—N2—H2N2	118.8	N3—C8—H8A	120.0
H1N2—N2—H2N2	119.1	C8—C9—C10	118.4 (2)
C7—N3—C8	124.15 (19)	C8—C9—H9A	120.8
C7—N3—H1N3	114.7 (15)	C10—C9—H9A	120.8
C8—N3—H1N3	121.1 (16)	C11—C10—C9	121.5 (2)
C6—C1—C2	119.35 (18)	C11—C10—H10A	119.2
C6—C1—S1	121.47 (15)	C9—C10—H10A	119.2
C2—C1—S1	119.17 (15)	C10—C11—C7	120.0 (2)
C3—C2—C1	120.26 (18)	C10—C11—H11A	120.0
C3—C2—H2A	119.9	C7—C11—H11A	120.0
C1—C2—H2A	119.9	O4—N4—O3	122.0 (3)
C2—C3—C4	120.77 (19)	O4—N4—C12	120.8 (3)
C2—C3—H3A	119.6	O3—N4—C12	117.2 (3)
C4—C3—H3A	119.6	N4—C12—H12A	109.5
N2—C4—C5	121.67 (19)	N4—C12—H12B	109.5
N2—C4—C3	120.14 (19)	H12A—C12—H12B	109.5
C5—C4—C3	118.18 (19)	N4—C12—H12C	109.5
C6—C5—C4	121.24 (18)	H12A—C12—H12C	109.5
C6—C5—H5A	119.4	H12B—C12—H12C	109.5
C4—C5—H5A	119.4

O2—S1—N1—C7	43.60 (19)	C3—C4—C5—C6	−3.3 (3)
O1—S1—N1—C7	170.79 (16)	C4—C5—C6—C1	1.3 (3)
C1—S1—N1—C7	−75.12 (17)	C2—C1—C6—C5	1.2 (3)
O2—S1—C1—C6	−0.9 (2)	S1—C1—C6—C5	−178.33 (17)
O1—S1—C1—C6	−126.50 (18)	S1—N1—C7—N3	176.39 (14)
N1—S1—C1—C6	121.65 (17)	S1—N1—C7—C11	−3.6 (3)
O2—S1—C1—C2	179.59 (16)	C8—N3—C7—N1	178.0 (2)
O1—S1—C1—C2	53.96 (18)	C8—N3—C7—C11	−2.0 (3)
N1—S1—C1—C2	−57.89 (18)	C7—N3—C8—C9	0.8 (4)
C6—C1—C2—C3	−1.6 (3)	N3—C8—C9—C10	0.6 (4)
S1—C1—C2—C3	177.94 (16)	C8—C9—C10—C11	−0.6 (5)
C1—C2—C3—C4	−0.5 (3)	C9—C10—C11—C7	−0.7 (4)
C2—C3—C4—N2	−178.6 (2)	N1—C7—C11—C10	−178.1 (2)
C2—C3—C4—C5	2.9 (3)	N3—C7—C11—C10	1.9 (3)
N2—C4—C5—C6	178.2 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1N2···O2ⁱ	0.87	2.10	2.971 (3)	174
N2—H2N2···O1ⁱⁱ	0.87	2.34	3.162 (3)	157
N3—H1N3···N1ⁱⁱⁱ	0.86 (2)	2.09 (2)	2.948 (2)	178 (2)
C8—H8A···O1ⁱⁱⁱ	0.93	2.52	3.160 (3)	126

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

Experimental details

Crystal data
Chemical formula	C₁₁H₁₁N₃O₂S·CH₃NO₂
M_r	310.34
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	296
a, b, c (Å)	10.5179 (3), 12.4857 (3), 22.7237 (6)
V (Å³)	2984.15 (14)
Z	8
Radiation type	Cu Kα
µ (mm⁻¹)	2.14
Crystal size (mm)	0.54 × 0.43 × 0.31

Data collection
Diffractometer	Bruker SMART APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.392, 0.554
No. of measured, independent and observed [I > 2σ(I)] reflections	14569, 2799, 2386
R_int	0.062
(sin θ/λ)_max (Å⁻¹)	0.615

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.144, 1.07
No. of reflections	2799
No. of parameters	196
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.25, −0.42

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1N2···O2ⁱ	0.87	2.10	2.971 (3)	174
N2—H2N2···O1ⁱⁱ	0.87	2.34	3.162 (3)	157
N3—H1N3···N1ⁱⁱⁱ	0.86 (2)	2.09 (2)	2.948 (2)	178 (2)
C8—H8A···O1ⁱⁱⁱ	0.93	2.52	3.160 (3)	126

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

Footnotes

‡Thomson Reuters ResearcherID: A-5085-2009.

§College of Pharmacy (Visiting Professor), King Saud University, PO Box 2457, Riyadh 11451, Saudi Arabia. Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

The authors are grateful for the sponsorship of the Research Center, College of Pharmacy and the Deanship of Scientific Research, King Saud University, Riyadh, Saudi Arabia. HKF and SC thank Universiti Sains Malaysia for the Research University Grant No. 1001/PFIZIK/811160. HKF also thanks the King Saud University, Riyadh, Saudi Arabia, for the award of a visiting Professorship (December 23rd 2011 to January 14th 2012).

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