2-Amino-1-(3-sulfonato­prop­yl)pyridinium monohydrate

Adam, F.; Ali, T.H.; Kueh, C.-W.; Rosli, M.M.; Fun, H.-K.

doi:10.1107/S1600536811004107

organic compounds

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ISSN: 2056-9890

Volume 67| Part 3| March 2011| Page o580

doi:10.1107/S1600536811004107

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2-Amino-1-(3-sulfonatopropyl)pyridinium monohydrate

Farook Adam,^a Tammar H. Ali,^a Chien-Wen Kueh,^a Mohd Mustaqim Rosli ^b and Hoong-Kun Fun ^b ^*‡

^aSchool of Chemical Sciences, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and ^bX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
^*Correspondence e-mail: hkfun@usm.my

(Received 16 January 2011; accepted 2 February 2011; online 5 February 2011)

In the title compound, C₈H₁₂N₂O₃S·H₂O, intermolecular O—H⋯O and N—H⋯O hydrogen bonds and weak C—H⋯O interactions, which form R₁²(6) and R₂²(12) ring motifs, link the components into a three-dimensional network.

Related literature

For applications of sulfopropyl derivatives, see: Adamczyk & Rege (1998 ). For the biological activity of 2-aminopyridine, see: Salimon et al. (2009 ). For a related structure, see: Koclega et al. (2007 ). For the title compound as a heterogeneous catalyst, see: Jayamurugan et al. (2009 ). For hydrogen-bond motifs, see: Bernstein et al. (1995 ). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ).

Experimental

Crystal data

C₈H₁₂N₂O₃S·H₂O
M_r = 234.27
Monoclinic, P 2₁ /c
a = 9.0771 (3) Å
b = 16.6307 (7) Å
c = 7.4393 (3) Å
β = 112.794 (1)°
V = 1035.32 (7) Å³
Z = 4
Mo Kα radiation
μ = 0.31 mm⁻¹
T = 100 K
0.51 × 0.14 × 0.14 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.858, T_max = 0.958
15075 measured reflections
4050 independent reflections
3694 reflections with I > 2σ(I)
R_int = 0.023

Refinement

R[F² > 2σ(F²)] = 0.028
wR(F²) = 0.082
S = 1.04
4050 reflections
152 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.49 e Å⁻³
Δρ_min = −0.41 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H1N2⋯O3ⁱ	0.862 (15)	2.009 (14)	2.8553 (10)	167.0 (13)
O1W—H1W1⋯O2ⁱⁱ	0.89 (2)	1.95 (2)	2.8289 (9)	171.5 (19)
N2—H2N2⋯O1W	0.875 (16)	2.055 (16)	2.9139 (11)	166.9 (15)
O1W—H2W1⋯O2ⁱⁱⁱ	0.822 (19)	2.007 (19)	2.8270 (10)	175 (2)
C1—H1A⋯O1^iv	0.93	2.57	3.4076 (11)	150
C2—H2A⋯O1W^v	0.93	2.58	3.3595 (11)	142
C6—H6A⋯O3ⁱ	0.97	2.53	3.3160 (11)	138
C6—H6B⋯O1^iv	0.97	2.52	3.2589 (11)	133
Symmetry codes: (i) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (ii) $[x+1, -y+{\script{1\over 2}}, z+{\script{3\over 2}}]$ ; (iii) x+1, y, z+1; (iv) -x, -y, -z; (v) $[-x+1, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

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/S1600536811004107/lh5199sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811004107/lh5199Isup2.hkl

checkCIF report

Comment top

The sulfopropyl group has been widely used as a hydrophilic enhancing agent in dye, nucleocides, proteins and polymers (Adamczyk & Rege, 1998). In addition, derivatives of sulfopropylated compounds are used extensively in both manufacturing and diagnostic industries. For example, sulfopropylated fatty acids have been found to possess antistatic properties while sulfopropylated acridines have been used industrially as chemiluminescent probes (Adamczyk & Rege, 1998). These properties of sultone can be acredited to the CH₂ group attached to the S atom which allowed attachment to other organic fragments such as the 2-amino pyridine group in the current study. The indisputable application of 2-aminopyridine in the synthesis of pharmaceuticals such as antihistamines and piroxican has been the main reason for its substantial desirability up to now (Salimon et al., 2009). In this study, sultone was reacted with 2-aminopyridine and attachment was achieved through the N atom in the ring. This compound allows the immobilization onto silica to serve as a heterogeneous catalyst in various industrial applications (Jayamurugan et al., 2009).

All parameters in the title compound (I), Fig. 1, are within normal ranges and comparable to a related structure (Koclega et al., 2007). The torsion angles S1-C8-C7-C6 and N1-C6-C7-C8 are -178.36 (5) and -179.58 (6)° respectively. In the selected asymmetric unit, the 2-amino-N-3-sulfatepropyl-pyridinium molecule is linked to the water molecule through an N2—H2N2···O1W (Table 1, Fig. 1) intermolecular hydrogen bond.

In the crystal structure, intermolecular O1W—H1W1···O2ⁱⁱ, O1W—H2W1···O2ⁱⁱⁱ, N2—H1N2···O3ⁱ, C6—H6B···O1^iv, C1—H1A···O1^iv, C2—H2A···O1W^v and weak C6—H6A···O3ⁱ hydrogen bnods (Table 1, Fig. 2) link molecules into a three-dimensional network. The weak C6—H6B···O1^iv interactions are involved in R₂²(12) ring motifs while weak C1—H1A···O1^iv interactions form R₁² (6) ring motifs (Bernstein et al., 1995).

Related literature top

For applications of sulfopropyl derivatives, see: Adamczyk & Rege (1998). For the biological activity of 2-aminopyridine, see: Salimon et al. (2009). For a related structure, see: Koclega et al. (2007). For the title compound as a heterogeneous catalyst, see: Jayamurugan et al. (2009). For hydrogen-bond motifs, see: Bernstein et al. (1995). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986).

Experimental top

2-amino pyridine (3g, 1.9 mmol) was dissolved in acetonitrile (20 ml). 1,3-propane sultone (2.8 ml, 1.9 mmol) was added to the mixture and was refluxed at 353 K for 1 h. The light yellowish precipitate was filtered and washed with acetonitrile (10 ml) and diethyl ether (10 ml). The product was recrystallized in methanol: water (9:1 ratio) to produce light yellow needle-shaped crystals.

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 molecular structure, showing 50% probability displacement ellipsoids. Hydrogen atoms are shown as spheres of arbitrary radius. The dashed line indicates a hydrogen bond.
	Fig. 2. The crystal packing of (I) viewed along the b axis. Dashed lines indicate hydrogen bonds. H atoms not involved in the hydrogen bond interactions have been omitted for clarity.

2-Amino-1-(3-sulfonatopropyl)pyridinium monohydrate top

Crystal data top

C₈H₁₂N₂O₃S·H₂O	F(000) = 496
M_r = 234.27	D_x = 1.503 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 7571 reflections
a = 9.0771 (3) Å	θ = 3.2–33.6°
b = 16.6307 (7) Å	µ = 0.31 mm⁻¹
c = 7.4393 (3) Å	T = 100 K
β = 112.794 (1)°	Needle, light-yellow
V = 1035.32 (7) Å³	0.51 × 0.14 × 0.14 mm
Z = 4

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	4050 independent reflections
Radiation source: fine-focus sealed tube	3694 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.023
ϕ and ω scans	θ_max = 33.6°, θ_min = 3.2°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −14→13
T_min = 0.858, T_max = 0.958	k = −24→25
15075 measured reflections	l = −11→11

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: inferred from neighbouring sites
wR(F²) = 0.082	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ²(F_o²) + (0.0443P)² + 0.3224P] where P = (F_o² + 2F_c²)/3
4050 reflections	(Δ/σ)_max < 0.001
152 parameters	Δρ_max = 0.49 e Å⁻³
0 restraints	Δρ_min = −0.41 e Å⁻³

Crystal data top

C₈H₁₂N₂O₃S·H₂O	V = 1035.32 (7) Å³
M_r = 234.27	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 9.0771 (3) Å	µ = 0.31 mm⁻¹
b = 16.6307 (7) Å	T = 100 K
c = 7.4393 (3) Å	0.51 × 0.14 × 0.14 mm
β = 112.794 (1)°

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	4050 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	3694 reflections with I > 2σ(I)
T_min = 0.858, T_max = 0.958	R_int = 0.023
15075 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.028	0 restraints
wR(F²) = 0.082	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 0.49 e Å⁻³
4050 reflections	Δρ_min = −0.41 e Å⁻³
152 parameters

Special details top

Experimental. The crystal was placed in the cold stream of an Oxford Cyrosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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	0.02015 (2)	0.135731 (11)	−0.20477 (3)	0.00995 (6)
O1	0.04125 (8)	0.05139 (4)	−0.23882 (9)	0.01617 (12)
O2	−0.13259 (7)	0.16825 (4)	−0.34346 (9)	0.01625 (12)
O3	0.15490 (7)	0.18591 (4)	−0.19553 (9)	0.01467 (12)
N1	0.29524 (8)	0.09165 (4)	0.54330 (9)	0.01030 (12)
N2	0.40686 (9)	0.22107 (4)	0.57767 (11)	0.01460 (13)
C1	0.30927 (10)	0.01161 (5)	0.59030 (12)	0.01312 (14)
H1A	0.2253	−0.0229	0.5236	0.016*
C2	0.44337 (10)	−0.01854 (5)	0.73247 (12)	0.01495 (14)
H2A	0.4531	−0.0733	0.7604	0.018*
C3	0.56716 (10)	0.03537 (5)	0.83638 (12)	0.01397 (14)
H3A	0.6577	0.0167	0.9384	0.017*
C4	0.55426 (9)	0.11494 (5)	0.78738 (11)	0.01314 (14)
H4A	0.6364	0.1502	0.8558	0.016*
C5	0.41636 (9)	0.14415 (5)	0.63289 (11)	0.01089 (13)
C6	0.14495 (9)	0.11861 (5)	0.38687 (11)	0.01081 (13)
H6A	0.1216	0.1734	0.4122	0.013*
H6B	0.0575	0.0846	0.3847	0.013*
C7	0.16001 (9)	0.11457 (5)	0.19015 (11)	0.01233 (13)
H7A	0.2483	0.1482	0.1932	0.015*
H7B	0.1829	0.0597	0.1649	0.015*
C8	0.00708 (9)	0.14264 (5)	0.02759 (11)	0.01198 (13)
H8A	−0.0140	0.1980	0.0514	0.014*
H8B	−0.0815	0.1100	0.0275	0.014*
O1W	0.71613 (8)	0.30058 (4)	0.75218 (10)	0.01777 (13)
H1N2	0.3233 (17)	0.2419 (8)	0.489 (2)	0.020 (3)*
H1W1	0.772 (2)	0.3125 (10)	0.877 (3)	0.034 (4)*
H2N2	0.4915 (18)	0.2508 (9)	0.636 (2)	0.025 (3)*
H2W1	0.765 (2)	0.2638 (11)	0.726 (3)	0.041 (5)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.01095 (9)	0.01021 (9)	0.00793 (9)	−0.00137 (6)	0.00282 (6)	−0.00137 (5)
O1	0.0228 (3)	0.0105 (3)	0.0159 (3)	−0.0020 (2)	0.0082 (2)	−0.0038 (2)
O2	0.0142 (3)	0.0222 (3)	0.0094 (2)	0.0024 (2)	0.0014 (2)	0.0011 (2)
O3	0.0156 (3)	0.0152 (3)	0.0138 (3)	−0.0060 (2)	0.0064 (2)	−0.0030 (2)
N1	0.0103 (3)	0.0104 (3)	0.0087 (3)	0.0005 (2)	0.0021 (2)	0.0004 (2)
N2	0.0123 (3)	0.0107 (3)	0.0165 (3)	−0.0005 (2)	0.0008 (2)	0.0015 (2)
C1	0.0153 (3)	0.0109 (3)	0.0126 (3)	−0.0007 (2)	0.0048 (3)	0.0004 (2)
C2	0.0169 (3)	0.0123 (3)	0.0147 (3)	0.0022 (3)	0.0051 (3)	0.0029 (3)
C3	0.0133 (3)	0.0157 (3)	0.0121 (3)	0.0033 (3)	0.0041 (3)	0.0022 (3)
C4	0.0110 (3)	0.0146 (3)	0.0115 (3)	0.0007 (3)	0.0018 (2)	0.0001 (3)
C5	0.0103 (3)	0.0112 (3)	0.0102 (3)	0.0003 (2)	0.0029 (2)	−0.0005 (2)
C6	0.0097 (3)	0.0128 (3)	0.0087 (3)	0.0008 (2)	0.0023 (2)	0.0003 (2)
C7	0.0113 (3)	0.0160 (3)	0.0090 (3)	0.0020 (3)	0.0032 (2)	0.0003 (2)
C8	0.0108 (3)	0.0156 (3)	0.0085 (3)	0.0015 (2)	0.0027 (2)	−0.0001 (2)
O1W	0.0167 (3)	0.0174 (3)	0.0147 (3)	0.0013 (2)	0.0010 (2)	−0.0018 (2)

Geometric parameters (Å, º) top

S1—O1	1.4511 (6)	C3—C4	1.3655 (12)
S1—O3	1.4602 (6)	C3—H3A	0.9300
S1—O2	1.4734 (6)	C4—C5	1.4174 (11)
S1—C8	1.7817 (8)	C4—H4A	0.9300
N1—C5	1.3593 (10)	C6—C7	1.5231 (11)
N1—C1	1.3695 (10)	C6—H6A	0.9700
N1—C6	1.4786 (10)	C6—H6B	0.9700
N2—C5	1.3361 (10)	C7—C8	1.5188 (11)
N2—H1N2	0.861 (14)	C7—H7A	0.9700
N2—H2N2	0.874 (15)	C7—H7B	0.9700
C1—C2	1.3616 (11)	C8—H8A	0.9700
C1—H1A	0.9300	C8—H8B	0.9700
C2—C3	1.4110 (12)	O1W—H1W1	0.892 (17)
C2—H2A	0.9300	O1W—H2W1	0.825 (19)

O1—S1—O3	113.32 (4)	C5—C4—H4A	119.8
O1—S1—O2	112.62 (4)	N2—C5—N1	121.38 (7)
O3—S1—O2	111.53 (4)	N2—C5—C4	120.60 (7)
O1—S1—C8	107.14 (4)	N1—C5—C4	118.02 (7)
O3—S1—C8	106.67 (4)	N1—C6—C7	110.12 (6)
O2—S1—C8	104.92 (4)	N1—C6—H6A	109.6
C5—N1—C1	121.44 (7)	C7—C6—H6A	109.6
C5—N1—C6	121.03 (7)	N1—C6—H6B	109.6
C1—N1—C6	117.50 (6)	C7—C6—H6B	109.6
C5—N2—H1N2	123.5 (9)	H6A—C6—H6B	108.2
C5—N2—H2N2	116.6 (10)	C8—C7—C6	110.91 (6)
H1N2—N2—H2N2	119.9 (14)	C8—C7—H7A	109.5
C2—C1—N1	121.53 (7)	C6—C7—H7A	109.5
C2—C1—H1A	119.2	C8—C7—H7B	109.5
N1—C1—H1A	119.2	C6—C7—H7B	109.5
C1—C2—C3	118.30 (8)	H7A—C7—H7B	108.0
C1—C2—H2A	120.9	C7—C8—S1	111.64 (6)
C3—C2—H2A	120.9	C7—C8—H8A	109.3
C4—C3—C2	120.12 (7)	S1—C8—H8A	109.3
C4—C3—H3A	119.9	C7—C8—H8B	109.3
C2—C3—H3A	119.9	S1—C8—H8B	109.3
C3—C4—C5	120.41 (8)	H8A—C8—H8B	108.0
C3—C4—H4A	119.8	H1W1—O1W—H2W1	105.9 (16)

C5—N1—C1—C2	1.82 (12)	C3—C4—C5—N2	−176.43 (8)
C6—N1—C1—C2	−179.98 (7)	C3—C4—C5—N1	3.44 (12)
N1—C1—C2—C3	2.11 (12)	C5—N1—C6—C7	87.55 (9)
C1—C2—C3—C4	−3.15 (12)	C1—N1—C6—C7	−90.66 (8)
C2—C3—C4—C5	0.38 (13)	N1—C6—C7—C8	−179.58 (6)
C1—N1—C5—N2	175.31 (8)	C6—C7—C8—S1	−178.36 (5)
C6—N1—C5—N2	−2.83 (12)	O1—S1—C8—C7	62.61 (7)
C1—N1—C5—C4	−4.56 (11)	O3—S1—C8—C7	−59.04 (7)
C6—N1—C5—C4	177.31 (7)	O2—S1—C8—C7	−177.48 (6)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1N2···O3ⁱ	0.862 (15)	2.009 (14)	2.8553 (10)	167.0 (13)
O1W—H1W1···O2ⁱⁱ	0.89 (2)	1.95 (2)	2.8289 (9)	171.5 (19)
N2—H2N2···O1W	0.875 (16)	2.055 (16)	2.9139 (11)	166.9 (15)
O1W—H2W1···O2ⁱⁱⁱ	0.822 (19)	2.007 (19)	2.8270 (10)	175 (2)
C1—H1A···O1^iv	0.93	2.57	3.4076 (11)	150
C2—H2A···O1W^v	0.93	2.58	3.3595 (11)	142
C6—H6A···O3ⁱ	0.97	2.53	3.3160 (11)	138
C6—H6B···O1^iv	0.97	2.52	3.2589 (11)	133

Symmetry codes: (i) x, −y+1/2, z+1/2; (ii) x+1, −y+1/2, z+3/2; (iii) x+1, y, z+1; (iv) −x, −y, −z; (v) −x+1, y−1/2, −z+3/2.

Experimental details

Crystal data
Chemical formula	C₈H₁₂N₂O₃S·H₂O
M_r	234.27
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	9.0771 (3), 16.6307 (7), 7.4393 (3)
β (°)	112.794 (1)
V (Å³)	1035.32 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.31
Crystal size (mm)	0.51 × 0.14 × 0.14

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.858, 0.958
No. of measured, independent and observed [I > 2σ(I)] reflections	15075, 4050, 3694
R_int	0.023
(sin θ/λ)_max (Å⁻¹)	0.779

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.028, 0.082, 1.04
No. of reflections	4050
No. of parameters	152
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.49, −0.41

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···O3ⁱ	0.862 (15)	2.009 (14)	2.8553 (10)	167.0 (13)
O1W—H1W1···O2ⁱⁱ	0.89 (2)	1.95 (2)	2.8289 (9)	171.5 (19)
N2—H2N2···O1W	0.875 (16)	2.055 (16)	2.9139 (11)	166.9 (15)
O1W—H2W1···O2ⁱⁱⁱ	0.822 (19)	2.007 (19)	2.8270 (10)	175 (2)
C1—H1A···O1^iv	0.93	2.57	3.4076 (11)	150
C2—H2A···O1W^v	0.93	2.58	3.3595 (11)	142
C6—H6A···O3ⁱ	0.97	2.53	3.3160 (11)	138
C6—H6B···O1^iv	0.97	2.52	3.2589 (11)	133

Symmetry codes: (i) x, −y+1/2, z+1/2; (ii) x+1, −y+1/2, z+3/2; (iii) x+1, y, z+1; (iv) −x, −y, −z; (v) −x+1, y−1/2, −z+3/2.

Footnotes

‡Thomson Reuters ResearcherID: A-3561-2009

Acknowledgements

The authors would like to thank Universiti Sains Malaysia (USM) for the RU research grant (No. 1001/PKIMIA/814019). CWK would also like to acknowledge an NSF scholarship. HKF and MMR also thank USM for the Research University Grant (No. 1001/PFIZIK/811160).

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