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Acta Crystallogr Sect E Struct Rep Online. 2008 March 1; 64(Pt 3): o606.
Published online 2008 February 20. doi:  10.1107/S1600536808002924
PMCID: PMC2960831

8,8-Dimethyl-5-(4-methyl­phen­yl)-8,9-dihydro­pyrimido[4,5-b]quinoline-2,4,6(1H,3H,7H)-trione N,N-dimethyl­formamide solvate

Abstract

The title compound, C20H19N3O3·C3H7NO, was synthesized by the reaction of 6-amino­pyrimidine-2,4(1H,3H)-dione and 4-methyl­benzaldehyde with 5,5-dimethyl-1,3-cyclo­hexa­nedione in 1-butyl-3-methyl­imidazolium bromide at 363 K. The pyrimidine ring adopts a half-chair conformation while the six-membered ring fused to the pyridine ring adopts a skew-boat conformation. The dihedral angle between the pyridine ring and the attached benzene ring is 2.38(8)°

Related literature

For related literature, see: Bhuyan et al. (1999 [triangle]); Clercq (1986 [triangle]); Gangjee et al. (1999 [triangle]); Griengl et al. (1987 [triangle]); Hirota et al. (1981 [triangle]); Jones et al. (1979 [triangle]); Nasr & Gineinah (2002 [triangle]); Pontikis & Monneret (1994 [triangle]); Sasaki et al. (1980 [triangle]).

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Object name is e-64-0o606-scheme1.jpg

Experimental

Crystal data

  • C20H19N3O3·C3H7NO
  • M r = 422.48
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-0o606-efi1.jpg
  • a = 8.8252 (16) Å
  • b = 10.289 (2) Å
  • c = 12.316 (2) Å
  • α = 95.898 (3)°
  • β = 93.115 (3)°
  • γ = 94.719 (3)°
  • V = 1106.4 (4) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 0.09 mm−1
  • T = 294 (2) K
  • 0.24 × 0.16 × 0.12 mm

Data collection

  • Bruker SMART 1000 diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.978, T max = 0.989
  • 6083 measured reflections
  • 4285 independent reflections
  • 2833 reflections with I > 2σ(I)
  • R int = 0.018

Refinement

  • R[F 2 > 2σ(F 2)] = 0.045
  • wR(F 2) = 0.134
  • S = 1.00
  • 4285 reflections
  • 285 parameters
  • 1 restraint
  • H-atom parameters constrained
  • Δρmax = 0.25 e Å−3
  • Δρmin = −0.23 e Å−3

Data collection: SMART (Bruker, 1998 [triangle]); cell refinement: SAINT (Bruker, 1999 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808002924/cs2057sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808002924/cs2057Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

The authors are grateful to the Foundation of the Key Laboratory of Biotechnology on Medical Plants of Jiangsu Province for financial support.

supplementary crystallographic information

Comment

The importance of uracil and its annelated derivatives is well recognized by synthetic (Sasaki et al., 1980; Bhuyan et al., 1999) as well as biological (Griengl et al., 1987; Pontikis et al., 1994) chemists. With the development of clinically useful anticancer and antiviral drugs (Clercq et al.,1986; Jones et al., 1979), there has recently been remarkable interest in the synthetic manipulations of uracils (Hirota et al., 1981). Pyrido[2,3-d]pyrimidines represent a heterocyclic ring system of considerable interest because of several biological activities associated with this scaffold. Some analogues have been found to act as anticancer agents inhibiting dihydrofolate reductases or tyrosine kinases (Gangjee et al., 1999), while others are known antiviral agents (Nasr et al., 2002).

The title compound was synthesized by the reaction of 6-aminopyrimidine-2,4(1H,3H)-dione and 4-methylbenzaldehyde with 5,5-dimethyl-1,3-cyclohexanedione using 1-butyl-3-methylimidazolium bromide ([bmim]Br) as solvent at 363 K.

In the title compound the pyridine ring (C13/C3/C4/C5/C12/N3) is a newly formed planar ring. The pyrimidine ring is less planar with atom C2 deviating from the C3/C1/C13/N1/N2 plane by -0.108 (3) Å (Fig. 1). The six-membered ring fused on to the pyridine ring adopts a skew-boat conformation; atoms C6, C5, C12 and C11 are coplanar, with atoms C7 and C8 deviating from the plane by -0.301 (2) and 0.458 (6) Å, respectively. The dihedral angle between the C13/C3/C4/C5/C12/N3 plane and the C3/C1/C13/N1/N2 plane is 2.38 (8) °, they are almost coplanar. The dihedral angle between the C13/C3/C4/C5/C12/N3 plane and the C14/C15/C16/C17/C19/C20 plane is 77.99 (5) °. The molecules are linked by N1—H1···O4 and N2—H2···O1 intermolecular hydrogen bonds (Table 1) to form dimers (Fig. 2).

Experimental

The title compound was prepared by the reaction of 6-aminopyrimidine-2,4(1H,3H)-dione (2 mmol) and 4-methylaldehyde (2 mmol) with 5,5-dimethyl-1,3-cyclohexanedione (2 mmol) in [bmim]Br (2 ml) at 363 K. Crystals of the title compound suitable for X-ray diffraction were obtained by slow evaporation of a N,N-dimethylformamide and water solution. 1H NMR (DMSO-d6, δ): 1.03 (6H, s, 2*CH3), 2.35 (3H, s, CH3), 2.40 (2H, s, CH2), 2.74 (3H, s, CH3), 2.90 (3H, s, CH3), 3.01 (2H, s, CH2), 6.89 (2H, d, J = 8.0 Hz, ArH), 7.08 (2H, d, J = 8.0 Hz, ArH), 7.96 (1H, s, CH), 11.12 (1H, s, NH), 11.88 (1H, s, NH).

Refinement

The amino H atoms were located in a difference map and kept riding subsequently. The C-bound H atoms were placed in calculated positions, with C—H = 0.93–0.97 Å, and included in the final cycles of refinement using a riding model, with Uiso(H) = 1.2–1.5 Ueq(C).

Figures

Fig. 1.
The molecular structure of the title compound showing 40% probability displacement ellipsoids and the atom-numbering scheme.
Fig. 2.
The crystal packing of the title compound.

Crystal data

C20H19N3O3·C3H7NOZ = 2
Mr = 422.48F000 = 448
Triclinic, P1Dx = 1.268 Mg m3
Hall symbol: -P 1Mo Kα radiation λ = 0.71073 Å
a = 8.8252 (16) ÅCell parameters from 2318 reflections
b = 10.289 (2) Åθ = 2.5–26.3º
c = 12.316 (2) ŵ = 0.09 mm1
α = 95.898 (3)ºT = 294 (2) K
β = 93.115 (3)ºBlock, colorless
γ = 94.719 (3)º0.24 × 0.16 × 0.12 mm
V = 1106.4 (4) Å3

Data collection

Bruker SMART 1000 diffractometer4285 independent reflections
Radiation source: fine-focus sealed tube2833 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.018
T = 294(2) Kθmax = 26.0º
[var phi] and ω scansθmin = 1.7º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)h = −9→10
Tmin = 0.978, Tmax = 0.989k = −10→12
6083 measured reflectionsl = −15→11

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.045H-atom parameters constrained
wR(F2) = 0.134  w = 1/[σ2(Fo2) + (0.0627P)2 + 0.2466P] where P = (Fo2 + 2Fc2)/3
S = 1.00(Δ/σ)max < 0.001
4285 reflectionsΔρmax = 0.25 e Å3
285 parametersΔρmin = −0.23 e Å3
1 restraintExtinction correction: none
Primary atom site location: structure-invariant direct methods

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

xyzUiso*/Ueq
O10.66314 (15)0.41510 (14)0.49822 (12)0.0587 (4)
O20.61458 (17)0.01747 (15)0.62264 (14)0.0726 (5)
O30.1315 (2)−0.03738 (19)0.88397 (19)0.1117 (8)
N10.63982 (17)0.22017 (16)0.56995 (13)0.0485 (4)
H10.73000.20420.54310.058*
N20.45129 (17)0.36219 (16)0.58594 (14)0.0503 (4)
H20.41120.43580.57040.060*
N30.24137 (17)0.32697 (15)0.68299 (13)0.0475 (4)
C10.5892 (2)0.33743 (19)0.54821 (16)0.0456 (5)
C20.5624 (2)0.1225 (2)0.62047 (16)0.0474 (5)
C30.42031 (19)0.15976 (18)0.66859 (14)0.0411 (4)
C40.3337 (2)0.08197 (18)0.73401 (14)0.0404 (4)
C50.1967 (2)0.12798 (18)0.76963 (15)0.0438 (4)
C60.0920 (2)0.0536 (2)0.83849 (18)0.0556 (5)
C7−0.0623 (2)0.10073 (19)0.85164 (18)0.0533 (5)
H7A−0.10910.06040.91080.064*
H7B−0.12590.07370.78510.064*
C8−0.0549 (2)0.25028 (19)0.87620 (16)0.0473 (5)
C90.0437 (3)0.2941 (2)0.98100 (19)0.0691 (6)
H9A0.04560.38750.99720.104*
H9B0.14550.27030.97160.104*
H9C0.00230.25201.04020.104*
C10−0.2145 (2)0.2942 (2)0.8905 (2)0.0650 (6)
H10A−0.25670.25740.95200.098*
H10B−0.27850.26470.82560.098*
H10C−0.20880.38820.90290.098*
C110.0129 (2)0.3077 (2)0.77834 (18)0.0544 (5)
H11A−0.06310.29440.71740.065*
H11B0.03500.40160.79660.065*
C120.1560 (2)0.25081 (18)0.74199 (16)0.0458 (5)
C130.36838 (19)0.27982 (18)0.64708 (15)0.0420 (4)
C140.38754 (19)−0.04296 (18)0.76792 (14)0.0398 (4)
C150.3251 (2)−0.16362 (19)0.71966 (16)0.0503 (5)
H150.2520−0.16840.66180.060*
C160.3704 (2)−0.2778 (2)0.75669 (18)0.0558 (5)
H160.3266−0.35840.72350.067*
C170.4790 (2)−0.2743 (2)0.84175 (17)0.0530 (5)
C180.5257 (3)−0.4007 (3)0.8817 (2)0.0871 (8)
H18A0.6009−0.43550.83620.131*
H18B0.4381−0.46320.87830.131*
H18C0.5675−0.38330.95590.131*
C190.5433 (2)−0.1537 (2)0.88808 (17)0.0548 (5)
H190.6181−0.14930.94480.066*
C200.4988 (2)−0.0388 (2)0.85185 (16)0.0485 (5)
H200.54420.04170.88420.058*
O4−0.06364 (17)0.16079 (19)0.51009 (14)0.0800 (5)
N40.09249 (19)0.25425 (17)0.39330 (15)0.0582 (5)
C210.0462 (2)0.1599 (3)0.45278 (19)0.0658 (6)
H210.10160.08680.45100.079*
C220.0147 (3)0.3718 (2)0.3888 (3)0.0941 (10)
H22A−0.06870.36940.43570.141*
H22B−0.02340.37720.31510.141*
H22C0.08450.44720.41280.141*
C230.2201 (3)0.2428 (3)0.3249 (2)0.0797 (8)
H23A0.26740.16430.33680.120*
H23B0.29280.31760.34310.120*
H23C0.18460.23900.24950.120*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.0489 (8)0.0557 (9)0.0800 (10)0.0090 (6)0.0278 (7)0.0317 (7)
O20.0714 (10)0.0658 (10)0.0973 (12)0.0368 (8)0.0439 (9)0.0436 (9)
O30.1149 (15)0.0955 (14)0.1588 (19)0.0597 (12)0.0936 (14)0.0921 (14)
N10.0396 (8)0.0558 (10)0.0574 (10)0.0151 (7)0.0189 (7)0.0236 (8)
N20.0446 (9)0.0477 (9)0.0676 (11)0.0153 (7)0.0225 (8)0.0298 (8)
N30.0434 (8)0.0466 (9)0.0597 (10)0.0131 (7)0.0181 (7)0.0249 (8)
C10.0395 (10)0.0480 (11)0.0535 (11)0.0077 (8)0.0124 (9)0.0168 (9)
C20.0473 (11)0.0521 (12)0.0497 (11)0.0165 (9)0.0143 (9)0.0232 (9)
C30.0396 (10)0.0441 (10)0.0441 (10)0.0110 (8)0.0097 (8)0.0163 (8)
C40.0429 (10)0.0408 (10)0.0412 (10)0.0100 (8)0.0087 (8)0.0132 (8)
C50.0440 (10)0.0443 (11)0.0478 (11)0.0098 (8)0.0142 (8)0.0162 (8)
C60.0633 (13)0.0447 (11)0.0665 (13)0.0131 (10)0.0296 (11)0.0229 (10)
C70.0485 (11)0.0497 (12)0.0646 (13)0.0020 (9)0.0198 (10)0.0141 (10)
C80.0420 (10)0.0464 (11)0.0575 (12)0.0090 (8)0.0173 (9)0.0138 (9)
C90.0749 (15)0.0634 (15)0.0693 (15)0.0109 (12)0.0075 (12)0.0036 (12)
C100.0516 (12)0.0669 (15)0.0824 (16)0.0141 (11)0.0280 (11)0.0164 (12)
C110.0459 (11)0.0571 (13)0.0687 (13)0.0190 (9)0.0227 (10)0.0263 (10)
C120.0432 (10)0.0462 (11)0.0533 (11)0.0113 (8)0.0145 (9)0.0194 (9)
C130.0376 (9)0.0447 (11)0.0484 (11)0.0088 (8)0.0120 (8)0.0190 (8)
C140.0409 (9)0.0410 (10)0.0422 (10)0.0103 (8)0.0136 (8)0.0163 (8)
C150.0527 (11)0.0477 (12)0.0514 (12)0.0066 (9)−0.0011 (9)0.0113 (9)
C160.0631 (13)0.0389 (11)0.0670 (14)0.0073 (9)0.0069 (11)0.0095 (10)
C170.0564 (12)0.0500 (13)0.0601 (13)0.0194 (10)0.0158 (10)0.0236 (10)
C180.0965 (19)0.0673 (17)0.109 (2)0.0288 (14)0.0107 (16)0.0448 (15)
C190.0550 (12)0.0627 (14)0.0508 (12)0.0155 (10)−0.0006 (10)0.0198 (10)
C200.0520 (11)0.0463 (11)0.0483 (11)0.0042 (9)0.0019 (9)0.0116 (9)
O40.0493 (9)0.1184 (15)0.0802 (11)0.0195 (9)0.0241 (8)0.0278 (10)
N40.0482 (10)0.0595 (11)0.0705 (12)0.0154 (8)0.0172 (9)0.0086 (9)
C210.0501 (12)0.0872 (18)0.0675 (15)0.0244 (12)0.0143 (11)0.0229 (13)
C220.0639 (15)0.0549 (15)0.166 (3)0.0120 (12)0.0356 (17)0.0052 (16)
C230.0733 (16)0.0849 (18)0.0918 (19)0.0286 (14)0.0400 (14)0.0257 (15)

Geometric parameters (Å, °)

O1—C11.226 (2)C10—H10C0.9600
O2—C21.211 (2)C11—C121.506 (2)
O3—C61.205 (2)C11—H11A0.9700
N1—C11.367 (2)C11—H11B0.9700
N1—C21.388 (2)C14—C151.378 (3)
N1—H10.8997C14—C201.382 (3)
N2—C11.360 (2)C15—C161.383 (3)
N2—C131.382 (2)C15—H150.9300
N2—H20.8952C16—C171.377 (3)
N3—C131.337 (2)C16—H160.9300
N3—C121.338 (2)C17—C191.375 (3)
C2—C31.478 (2)C17—C181.516 (3)
C3—C131.398 (2)C18—H18A0.9600
C3—C41.405 (2)C18—H18B0.9600
C4—C51.409 (2)C18—H18C0.9600
C4—C141.497 (2)C19—C201.384 (3)
C5—C121.411 (2)C19—H190.9300
C5—C61.503 (2)C20—H200.9300
C6—C71.495 (3)O4—C211.230 (2)
C7—C81.533 (3)N4—C211.326 (3)
C7—H7A0.9700N4—C221.444 (3)
C7—H7B0.9700N4—C231.447 (3)
C8—C91.523 (3)C21—H210.9300
C8—C111.526 (3)C22—H22A0.9600
C8—C101.528 (3)C22—H22B0.9600
C9—H9A0.9600C22—H22C0.9600
C9—H9B0.9600C23—H23A0.9600
C9—H9C0.9600C23—H23B0.9600
C10—H10A0.9600C23—H23C0.9600
C10—H10B0.9600
C1—N1—C2127.04 (15)C12—C11—H11B108.5
C1—N1—H1114.5C8—C11—H11B108.5
C2—N1—H1118.3H11A—C11—H11B107.5
C1—N2—C13123.74 (15)N3—C12—C5123.18 (16)
C1—N2—H2118.6N3—C12—C11114.43 (16)
C13—N2—H2117.6C5—C12—C11122.38 (16)
C13—N3—C12116.77 (15)N3—C13—N2114.21 (15)
O1—C1—N2122.24 (17)N3—C13—C3125.32 (15)
O1—C1—N1122.30 (16)N2—C13—C3120.46 (15)
N2—C1—N1115.46 (16)C15—C14—C20118.52 (17)
O2—C2—N1119.28 (17)C15—C14—C4121.53 (17)
O2—C2—C3125.96 (17)C20—C14—C4119.91 (17)
N1—C2—C3114.75 (16)C14—C15—C16120.51 (19)
C13—C3—C4117.92 (15)C14—C15—H15119.7
C13—C3—C2117.88 (15)C16—C15—H15119.7
C4—C3—C2124.20 (16)C17—C16—C15121.3 (2)
C3—C4—C5117.59 (16)C17—C16—H16119.4
C3—C4—C14121.21 (15)C15—C16—H16119.4
C5—C4—C14121.17 (15)C19—C17—C16117.98 (18)
C4—C5—C12119.14 (16)C19—C17—C18121.7 (2)
C4—C5—C6123.10 (16)C16—C17—C18120.4 (2)
C12—C5—C6117.74 (16)C17—C18—H18A109.5
O3—C6—C7121.12 (18)C17—C18—H18B109.5
O3—C6—C5121.92 (19)H18A—C18—H18B109.5
C7—C6—C5116.92 (17)C17—C18—H18C109.5
C6—C7—C8111.96 (16)H18A—C18—H18C109.5
C6—C7—H7A109.2H18B—C18—H18C109.5
C8—C7—H7A109.2C17—C19—C20121.29 (19)
C6—C7—H7B109.2C17—C19—H19119.4
C8—C7—H7B109.2C20—C19—H19119.4
H7A—C7—H7B107.9C14—C20—C19120.40 (19)
C9—C8—C11111.19 (18)C14—C20—H20119.8
C9—C8—C10108.88 (18)C19—C20—H20119.8
C11—C8—C10109.94 (16)C21—N4—C22122.15 (19)
C9—C8—C7109.80 (17)C21—N4—C23121.93 (19)
C11—C8—C7106.70 (16)C22—N4—C23115.86 (19)
C10—C8—C7110.32 (16)O4—C21—N4125.7 (2)
C8—C9—H9A109.5O4—C21—H21117.2
C8—C9—H9B109.5N4—C21—H21117.2
H9A—C9—H9B109.5N4—C22—H22A109.5
C8—C9—H9C109.5N4—C22—H22B109.5
H9A—C9—H9C109.5H22A—C22—H22B109.5
H9B—C9—H9C109.5N4—C22—H22C109.5
C8—C10—H10A109.5H22A—C22—H22C109.5
C8—C10—H10B109.5H22B—C22—H22C109.5
H10A—C10—H10B109.5N4—C23—H23A109.5
C8—C10—H10C109.5N4—C23—H23B109.5
H10A—C10—H10C109.5H23A—C23—H23B109.5
H10B—C10—H10C109.5N4—C23—H23C109.5
C12—C11—C8114.94 (16)H23A—C23—H23C109.5
C12—C11—H11A108.5H23B—C23—H23C109.5
C8—C11—H11A108.5
C13—N2—C1—O1−176.75 (19)C13—N3—C12—C11−178.87 (17)
C13—N2—C1—N13.2 (3)C4—C5—C12—N30.0 (3)
C2—N1—C1—O1−176.3 (2)C6—C5—C12—N3178.69 (19)
C2—N1—C1—N23.8 (3)C4—C5—C12—C11−179.04 (18)
C1—N1—C2—O2171.4 (2)C6—C5—C12—C11−0.4 (3)
C1—N1—C2—C3−9.2 (3)C8—C11—C12—N3−159.06 (18)
O2—C2—C3—C13−172.7 (2)C8—C11—C12—C520.1 (3)
N1—C2—C3—C138.0 (3)C12—N3—C13—N2179.51 (17)
O2—C2—C3—C47.0 (3)C12—N3—C13—C3−1.7 (3)
N1—C2—C3—C4−172.41 (18)C1—N2—C13—N3175.18 (18)
C13—C3—C4—C52.6 (3)C1—N2—C13—C3−3.7 (3)
C2—C3—C4—C5−176.97 (18)C4—C3—C13—N3−0.6 (3)
C13—C3—C4—C14−175.28 (17)C2—C3—C13—N3179.01 (18)
C2—C3—C4—C145.1 (3)C4—C3—C13—N2178.07 (17)
C3—C4—C5—C12−2.4 (3)C2—C3—C13—N2−2.3 (3)
C14—C4—C5—C12175.53 (18)C3—C4—C14—C15−104.4 (2)
C3—C4—C5—C6179.03 (18)C5—C4—C14—C1577.8 (2)
C14—C4—C5—C6−3.1 (3)C3—C4—C14—C2077.8 (2)
C4—C5—C6—O313.9 (4)C5—C4—C14—C20−100.1 (2)
C12—C5—C6—O3−164.7 (2)C20—C14—C15—C161.7 (3)
C4—C5—C6—C7−168.34 (19)C4—C14—C15—C16−176.17 (17)
C12—C5—C6—C713.1 (3)C14—C15—C16—C17−0.4 (3)
O3—C6—C7—C8132.9 (3)C15—C16—C17—C19−1.0 (3)
C5—C6—C7—C8−45.0 (3)C15—C16—C17—C18179.4 (2)
C6—C7—C8—C9−59.3 (2)C16—C17—C19—C201.0 (3)
C6—C7—C8—C1161.3 (2)C18—C17—C19—C20−179.3 (2)
C6—C7—C8—C10−179.26 (18)C15—C14—C20—C19−1.6 (3)
C9—C8—C11—C1270.9 (2)C4—C14—C20—C19176.28 (17)
C10—C8—C11—C12−168.42 (18)C17—C19—C20—C140.3 (3)
C7—C8—C11—C12−48.8 (2)C22—N4—C21—O4−0.6 (4)
C13—N3—C12—C52.0 (3)C23—N4—C21—O4−177.7 (2)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N1—H1···O4i0.901.962.854 (2)170
N2—H2···O1ii0.901.972.846 (2)167

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CS2057).

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