1,1′-(Butane-1,4-diyl)di-1H-imidazole–benzene-1,3,5-triol–water (1/1/1)

Gao, J.-S.; Yu, Y.-H.; Hou, G.-F.

doi:10.1107/S160053680802240X

organic compounds

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ISSN: 2056-9890

Volume 64| Part 8| August 2008| Page o1560

doi:10.1107/S160053680802240X

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1,1′-(Butane-1,4-diyl)di-1H-imidazole–benzene-1,3,5-triol–water (1/1/1)

Jin-Sheng Gao,^a ^* Ying-Hui Yu ^a and Guang-Feng Hou ^a

^aCollege of Chemistry and Materials Science, Heilongjiang University, Harbin 150080, People's Republic of China
^*Correspondence e-mail: hgf1000@163.com

(Received 11 June 2008; accepted 17 July 2008; online 19 July 2008)

The asymmetric unit of the title compound, C₁₀H₁₄N₄·C₆H₆O₃·H₂O, contains one molecule of benzene-1,3,5-triol, two half-molecules of 1,1′-butane-1,4-diyldi-1H-imidazole (each molecule is centrosymmetric) and one solvent water molecule. In the crystal structure, intermolecular O—H⋯O and O—H⋯N hydrogen bonds link all molecules into a three-dimensional supramolecular network.

Related literature

For background and details of the synthesis of 1,1′-(1,4-butanediyl)diimidazole, see: Ma et al. (2003 ). For the related crystal structure of 1,1′-(1,4-butanediyl)diimidazole, see: Yu et al. (2008 ).

Experimental

Crystal data

C₁₀H₁₄N₄·C₆H₆O₃·H₂O
M_r = 334.38
Triclinic, $[P \overline 1]$
a = 7.964 (5) Å
b = 8.405 (7) Å
c = 14.800 (9) Å
α = 98.40 (3)°
β = 92.93 (2)°
γ = 117.47 (3)°
V = 861.5 (10) Å³
Z = 2
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 291 (2) K
0.31 × 0.31 × 0.19 mm

Data collection

Rigaku R-AXIS RAPID diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ) T_min = 0.971, T_max = 0.982
8527 measured reflections
3911 independent reflections
2370 reflections with I > 2σ(I)
R_int = 0.028

Refinement

R[F² > 2σ(F²)] = 0.057
wR(F²) = 0.195
S = 1.05
3911 reflections
220 parameters
H-atom parameters constrained
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.27 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H22⋯O2	0.85	1.94	2.789 (3)	176
O4—H21⋯O1ⁱ	0.85	2.02	2.751 (3)	143
O3—H2⋯O4ⁱⁱ	0.82	1.84	2.658 (3)	173
O2—H6⋯N2ⁱⁱⁱ	0.82	1.84	2.636 (3)	164
O1—H4⋯N4^iv	0.82	1.79	2.596 (3)	170
Symmetry codes: (i) x, y+1, z; (ii) x-1, y-1, z; (iii) -x+2, -y+1, -z+1; (iv) x, y-1, z.

Data collection: RAPID-AUTO (Rigaku, 1998 ); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002 ); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680802240X/cv2422sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053680802240X/cv2422Isup2.hkl

checkCIF report

Comment top

The 1,1'-(1,4-butanediyl)diimidazole can be used as a flexible ligand to construct coordination polymer materials (Ma et al., 2003; Yu et al., 2008). In this paper, we report the new title compound, (I), synthesized by the reaction of 1,1'-(1,4-butanediyl)diimidazole and m-trihydroxybenzene in an methanol solution.

The asymmetric unit of the title compound, C₁₀H₁₄N₄.C₆H₆O₃.H₂O, contains one molecule of benzene-1,3,5-triol, two halfs of two independent centrosymmetric molecules of 1,1'-butane-1,4-diyldi-1H-imidazole and one crystalline water molecule (Figure 1). The two 1,1'-(1,4-butanediyl)diimidazole molecules both lie on inversion center.

There are five symmetry independent 'active' H atoms in the crystal structure; all of them participate in hydrogen bonds, which link the 1,1'-(1,4-butanediyl)diimidazole molecules, m-trihydroxybenzene molecule and water solvent molecule into an infinite three-dimensional network (Table 1, Figure 2).

Related literature top

For background and details of the synthesis of 1,1'-(1,4-butanediyl)diimidazole, see Ma et al. (2003). For the related crystal structure of 1,1'-(1,4-butanediyl)diimidazole, see Yu et al., (2008).

Experimental top

1,1'-(1,4-Butanediyl)diimidazole was prepared from imidazole and 1,4-dibromobutane in dimethylsulfoxide solution (Ma et al., 2003). m-trihydroxybenzene (0.126 g, 1 mmol) and 1,1'-(1,4-butanediyl)diimidazole (0.380 g, 2 mmol) were dissolved in hot methanol solution (15 ml) then a clear solution was obtained. The resulting solution was allowed to stand in a desiccator at room temperature for several days. Red crystals of (I) were obtained.

Computing details top

Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO (Rigaku, 1998); data reduction: CrystalStructure (Rigaku/MSC, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. A portion of the crystal structure of (I), showing the atomic numbering and 30% probability displacement ellipsoids [symmetry code: (I) -x, -y, -z + 1; (II) -x, -y, -z]. Dashed line indicates the hydrogen-bonding interaction.
	Fig. 2. A partial packing view, showing the three-dimensional hydrogen-bonding network. Dashed lines indicate the hydrogen-bonding interactions. H atoms have been omitted for clarity.

1,1'-(Butane-1,4-diyl)di-1H-imidazole–benzene-1,3,5-triol–water (1/1/1) top

Crystal data top

C₁₀H₁₄N₄·C₆H₆O₃·H₂O	Z = 2
M_r = 334.38	F(000) = 356
Triclinic, P1	D_x = 1.289 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.964 (5) Å	Cell parameters from 5362 reflections
b = 8.405 (7) Å	θ = 3.1–27.6°
c = 14.800 (9) Å	µ = 0.09 mm⁻¹
α = 98.40 (3)°	T = 291 K
β = 92.93 (2)°	Block, red
γ = 117.47 (3)°	0.31 × 0.31 × 0.19 mm
V = 861.5 (10) Å³

Data collection top

Rigaku R-AXIS RAPID diffractometer	3911 independent reflections
Radiation source: fine-focus sealed tube	2370 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.028
ω scans	θ_max = 27.5°, θ_min = 3.1°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −10→10
T_min = 0.971, T_max = 0.982	k = −10→10
8527 measured reflections	l = −18→19

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)] = 0.057	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.195	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.1078P)² + 0.0441P] where P = (F_o² + 2F_c²)/3
3911 reflections	(Δ/σ)_max < 0.001
220 parameters	Δρ_max = 0.20 e Å⁻³
0 restraints	Δρ_min = −0.27 e Å⁻³

Crystal data top

C₁₀H₁₄N₄·C₆H₆O₃·H₂O	γ = 117.47 (3)°
M_r = 334.38	V = 861.5 (10) Å³
Triclinic, P1	Z = 2
a = 7.964 (5) Å	Mo Kα radiation
b = 8.405 (7) Å	µ = 0.09 mm⁻¹
c = 14.800 (9) Å	T = 291 K
α = 98.40 (3)°	0.31 × 0.31 × 0.19 mm
β = 92.93 (2)°

Data collection top

Rigaku R-AXIS RAPID diffractometer	3911 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	2370 reflections with I > 2σ(I)
T_min = 0.971, T_max = 0.982	R_int = 0.028
8527 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.057	0 restraints
wR(F²) = 0.195	H-atom parameters constrained
S = 1.05	Δρ_max = 0.20 e Å⁻³
3911 reflections	Δρ_min = −0.27 e Å⁻³
220 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
C1	0.6082 (3)	0.4322 (3)	0.27525 (15)	0.0495 (5)
H1	0.5935	0.5359	0.2907	0.059*
C2	0.4512 (3)	0.2634 (3)	0.24735 (14)	0.0463 (5)
C3	0.4707 (3)	0.1074 (3)	0.22121 (14)	0.0440 (5)
H3	0.3639	−0.0060	0.2009	0.053*
C4	0.6534 (3)	0.1248 (3)	0.22616 (14)	0.0431 (5)
C5	0.8124 (3)	0.2923 (3)	0.25642 (14)	0.0445 (5)
H5	0.9340	0.3024	0.2609	0.053*
C6	0.7880 (3)	0.4458 (3)	0.28012 (14)	0.0461 (5)
C7	0.5669 (4)	0.2164 (4)	0.62310 (17)	0.0599 (6)
H7	0.5388	0.1550	0.6722	0.072*
C8	0.7113 (4)	0.4008 (4)	0.5372 (2)	0.0807 (9)
H8	0.8061	0.4952	0.5144	0.097*
C9	0.5333 (4)	0.2938 (5)	0.4948 (2)	0.0814 (9)
H9	0.4827	0.2997	0.4381	0.098*
C10	0.2441 (4)	0.0249 (4)	0.5326 (2)	0.0770 (8)
H10	0.2144	−0.0270	0.5878	0.092*
H11	0.2360	−0.0698	0.4837	0.092*
C11	0.0998 (3)	0.0796 (4)	0.50659 (19)	0.0655 (7)
H12	0.1248	0.1263	0.4498	0.079*
H13	0.1094	0.1768	0.5543	0.079*
C12	0.2720 (3)	0.5418 (3)	0.10952 (16)	0.0561 (6)
H16	0.2520	0.5172	0.1684	0.067*
C13	0.3851 (4)	0.6740 (4)	−0.00145 (17)	0.0606 (6)
H14	0.4595	0.7618	−0.0344	0.073*
C14	0.2445 (4)	0.5074 (4)	−0.03878 (17)	0.0613 (6)
H15	0.2052	0.4582	−0.1013	0.074*
C15	0.0159 (3)	0.2379 (3)	0.02391 (18)	0.0572 (6)
H17	−0.0806	0.2134	−0.0265	0.069*
H18	−0.0429	0.2277	0.0801	0.069*
C16	0.0830 (3)	0.0959 (3)	0.00706 (15)	0.0502 (6)
H19	0.1731	0.1147	0.0593	0.060*
H20	0.1485	0.1102	−0.0471	0.060*
N1	0.4412 (3)	0.1758 (3)	0.54990 (13)	0.0574 (5)
N2	0.7338 (3)	0.3514 (3)	0.61894 (15)	0.0661 (6)
N3	0.1703 (3)	0.4238 (2)	0.03210 (12)	0.0497 (5)
N4	0.4031 (3)	0.6959 (3)	0.09239 (14)	0.0573 (5)
O1	0.6793 (2)	−0.0244 (2)	0.20167 (12)	0.0587 (5)
H4	0.5847	−0.1054	0.1677	0.088*
O2	0.9405 (2)	0.6159 (2)	0.30773 (14)	0.0675 (5)
H6	1.0348	0.6068	0.3247	0.101*
O3	0.2755 (2)	0.2535 (2)	0.24808 (13)	0.0643 (5)
H2	0.1939	0.1464	0.2426	0.096*
O4	0.9883 (2)	0.9172 (3)	0.23236 (15)	0.0838 (6)
H21	0.8952	0.9328	0.2485	0.101*
H22	0.9716	0.8225	0.2530	0.101*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0515 (13)	0.0396 (12)	0.0590 (13)	0.0239 (11)	0.0033 (10)	0.0078 (10)
C2	0.0425 (11)	0.0467 (13)	0.0518 (12)	0.0225 (10)	0.0043 (9)	0.0113 (9)
C3	0.0374 (10)	0.0401 (12)	0.0503 (11)	0.0165 (9)	−0.0001 (9)	0.0055 (9)
C4	0.0432 (11)	0.0403 (12)	0.0464 (11)	0.0210 (10)	0.0037 (9)	0.0067 (9)
C5	0.0380 (11)	0.0443 (13)	0.0502 (11)	0.0192 (10)	0.0014 (9)	0.0090 (9)
C6	0.0416 (11)	0.0352 (12)	0.0532 (12)	0.0118 (10)	0.0007 (9)	0.0086 (9)
C7	0.0559 (14)	0.0609 (16)	0.0589 (14)	0.0246 (13)	0.0035 (11)	0.0120 (12)
C8	0.0605 (17)	0.069 (2)	0.117 (2)	0.0253 (16)	0.0187 (17)	0.0479 (18)
C9	0.074 (2)	0.096 (2)	0.0739 (17)	0.0352 (19)	0.0028 (15)	0.0350 (16)
C10	0.0540 (16)	0.0608 (18)	0.104 (2)	0.0216 (14)	−0.0041 (15)	0.0053 (15)
C11	0.0538 (14)	0.0644 (17)	0.0701 (15)	0.0261 (13)	−0.0046 (12)	0.0007 (13)
C12	0.0588 (14)	0.0445 (14)	0.0537 (13)	0.0177 (12)	0.0049 (11)	0.0011 (10)
C13	0.0570 (14)	0.0543 (16)	0.0706 (16)	0.0231 (13)	0.0136 (12)	0.0216 (12)
C14	0.0626 (15)	0.0632 (17)	0.0537 (13)	0.0266 (14)	0.0070 (12)	0.0095 (12)
C15	0.0451 (12)	0.0400 (13)	0.0717 (15)	0.0117 (10)	0.0073 (11)	−0.0024 (11)
C16	0.0418 (12)	0.0415 (13)	0.0559 (12)	0.0134 (10)	0.0030 (10)	0.0000 (10)
N1	0.0483 (11)	0.0548 (13)	0.0616 (12)	0.0200 (10)	−0.0006 (9)	0.0080 (10)
N2	0.0545 (13)	0.0524 (13)	0.0832 (15)	0.0220 (11)	−0.0070 (11)	0.0064 (11)
N3	0.0477 (10)	0.0376 (11)	0.0563 (11)	0.0159 (9)	0.0070 (9)	0.0026 (8)
N4	0.0512 (11)	0.0358 (11)	0.0724 (13)	0.0131 (9)	0.0036 (10)	0.0020 (9)
O1	0.0444 (9)	0.0438 (9)	0.0818 (12)	0.0222 (8)	−0.0023 (8)	−0.0069 (8)
O2	0.0494 (10)	0.0371 (9)	0.1014 (13)	0.0126 (8)	−0.0109 (9)	0.0056 (9)
O3	0.0432 (9)	0.0548 (11)	0.0984 (13)	0.0274 (8)	0.0079 (9)	0.0107 (10)
O4	0.0461 (10)	0.0723 (14)	0.1375 (18)	0.0247 (10)	0.0120 (11)	0.0456 (12)

Geometric parameters (Å, º) top

C1—C2	1.373 (3)	C11—C11ⁱ	1.512 (5)
C1—C6	1.380 (3)	C11—H12	0.9700
C1—H1	0.9300	C11—H13	0.9700
C2—O3	1.364 (3)	C12—N4	1.306 (3)
C2—C3	1.392 (3)	C12—N3	1.336 (3)
C3—C4	1.390 (3)	C12—H16	0.9300
C3—H3	0.9300	C13—C14	1.335 (4)
C4—O1	1.364 (3)	C13—N4	1.365 (3)
C4—C5	1.378 (3)	C13—H14	0.9300
C5—C6	1.390 (3)	C14—N3	1.356 (3)
C5—H5	0.9300	C14—H15	0.9300
C6—O2	1.365 (3)	C15—N3	1.458 (3)
C7—N2	1.302 (3)	C15—C16	1.512 (3)
C7—N1	1.326 (3)	C15—H17	0.9700
C7—H7	0.9300	C15—H18	0.9700
C8—C9	1.334 (4)	C16—C16ⁱⁱ	1.516 (4)
C8—N2	1.364 (4)	C16—H19	0.9700
C8—H8	0.9300	C16—H20	0.9700
C9—N1	1.347 (4)	O1—H4	0.8200
C9—H9	0.9300	O2—H6	0.8200
C10—N1	1.471 (3)	O3—H2	0.8200
C10—C11	1.475 (4)	O4—H21	0.8501
C10—H10	0.9700	O4—H22	0.8500
C10—H11	0.9700

C2—C1—C6	119.1 (2)	C10—C11—H13	109.4
C2—C1—H1	120.4	C11ⁱ—C11—H13	109.4
C6—C1—H1	120.4	H12—C11—H13	108.0
O3—C2—C1	117.6 (2)	N4—C12—N3	111.8 (2)
O3—C2—C3	121.2 (2)	N4—C12—H16	124.1
C1—C2—C3	121.2 (2)	N3—C12—H16	124.1
C4—C3—C2	118.5 (2)	C14—C13—N4	109.7 (2)
C4—C3—H3	120.7	C14—C13—H14	125.1
C2—C3—H3	120.7	N4—C13—H14	125.1
O1—C4—C5	118.36 (19)	C13—C14—N3	106.8 (2)
O1—C4—C3	120.58 (19)	C13—C14—H15	126.6
C5—C4—C3	121.07 (19)	N3—C14—H15	126.6
C4—C5—C6	118.88 (19)	N3—C15—C16	112.84 (19)
C4—C5—H5	120.6	N3—C15—H17	109.0
C6—C5—H5	120.6	C16—C15—H17	109.0
O2—C6—C1	117.4 (2)	N3—C15—H18	109.0
O2—C6—C5	121.5 (2)	C16—C15—H18	109.0
C1—C6—C5	121.1 (2)	H17—C15—H18	107.8
N2—C7—N1	112.9 (2)	C15—C16—C16ⁱⁱ	111.3 (2)
N2—C7—H7	123.6	C15—C16—H19	109.4
N1—C7—H7	123.6	C16ⁱⁱ—C16—H19	109.4
C9—C8—N2	110.0 (3)	C15—C16—H20	109.4
C9—C8—H8	125.0	C16ⁱⁱ—C16—H20	109.4
N2—C8—H8	125.0	H19—C16—H20	108.0
C8—C9—N1	106.8 (3)	C7—N1—C9	106.2 (2)
C8—C9—H9	126.6	C7—N1—C10	125.6 (2)
N1—C9—H9	126.6	C9—N1—C10	128.2 (2)
N1—C10—C11	113.9 (2)	C7—N2—C8	104.1 (2)
N1—C10—H10	108.8	C12—N3—C14	106.6 (2)
C11—C10—H10	108.8	C12—N3—C15	127.4 (2)
N1—C10—H11	108.8	C14—N3—C15	126.0 (2)
C11—C10—H11	108.8	C12—N4—C13	105.2 (2)
H10—C10—H11	107.7	C4—O1—H4	109.5
C10—C11—C11ⁱ	111.3 (3)	C6—O2—H6	109.5
C10—C11—H12	109.4	C2—O3—H2	109.5
C11ⁱ—C11—H12	109.4	H21—O4—H22	102.9

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O4—H22···O2	0.85	1.94	2.789 (3)	176
O4—H21···O1ⁱⁱⁱ	0.85	2.02	2.751 (3)	143
O3—H2···O4^iv	0.82	1.84	2.658 (3)	173
O2—H6···N2^v	0.82	1.84	2.636 (3)	164
O1—H4···N4^vi	0.82	1.79	2.596 (3)	170

Symmetry codes: (iii) x, y+1, z; (iv) x−1, y−1, z; (v) −x+2, −y+1, −z+1; (vi) x, y−1, z.

Experimental details

Crystal data
Chemical formula	C₁₀H₁₄N₄·C₆H₆O₃·H₂O
M_r	334.38
Crystal system, space group	Triclinic, P1
Temperature (K)	291
a, b, c (Å)	7.964 (5), 8.405 (7), 14.800 (9)
α, β, γ (°)	98.40 (3), 92.93 (2), 117.47 (3)
V (Å³)	861.5 (10)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.31 × 0.31 × 0.19

Data collection
Diffractometer	Rigaku R-AXIS RAPID diffractometer
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995)
T_min, T_max	0.971, 0.982
No. of measured, independent and observed [I > 2σ(I)] reflections	8527, 3911, 2370
R_int	0.028
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.057, 0.195, 1.05
No. of reflections	3911
No. of parameters	220
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.20, −0.27

Computer programs: RAPID-AUTO (Rigaku, 1998), CrystalStructure (Rigaku/MSC, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O4—H22···O2	0.85	1.94	2.789 (3)	176.4
O4—H21···O1ⁱ	0.85	2.02	2.751 (3)	143.3
O3—H2···O4ⁱⁱ	0.82	1.84	2.658 (3)	172.6
O2—H6···N2ⁱⁱⁱ	0.82	1.84	2.636 (3)	164.3
O1—H4···N4^iv	0.82	1.79	2.596 (3)	169.5

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

Acknowledgements

The authors thank Heilongjiang University for supporting this study.

References

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