organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890

5-tert-Butyl 3-ethyl 1-iso­propyl-4,5,6,7-tetra­hydro-1H-pyrazolo­[4,3-c]pyridine-3,5-di­carboxyl­ate

aMicroscale Science Institute, Weifang University, Weifang 261061, People's Republic of China
*Correspondence e-mail: huanmeiguo@163.com

(Received 26 October 2011; accepted 3 November 2011; online 9 November 2011)

In the title compound, C17H27N3O4, the six-membered ring adopts a half-chair conformation with the N atom and the adjacent methyl­ene C atom displaced by −0.391 (2) and 0.358 (2) Å, respectively, from the plane of the other four atoms. In the crystal, mol­ecules are linked by weak C—H⋯O inter­actions.

Related literature

For a related structure and background references to heterocycles as pharmaceuticals, see: Guo (2011[Guo, H.-M. (2011). Acta Cryst. E67, o2516.]).

[Scheme 1]

Experimental

Crystal data
  • C17H27N3O4

  • Mr = 337.42

  • Monoclinic, P 21 /c

  • a = 13.017 (3) Å

  • b = 12.771 (3) Å

  • c = 11.952 (3) Å

  • β = 115.760 (3)°

  • V = 1789.4 (7) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.09 mm−1

  • T = 173 K

  • 0.21 × 0.17 × 0.06 mm

Data collection
  • Rigaku MM007-HF CCD (Saturn 724+) diffractometer

  • Absorption correction: multi-scan (CrystalClear; Rigaku, 2007[Rigaku (2007). CrystalClear. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.981, Tmax = 0.995

  • 7844 measured reflections

  • 4013 independent reflections

  • 3330 reflections with I > 2σ(I)

  • Rint = 0.039

Refinement
  • R[F2 > 2σ(F2)] = 0.060

  • wR(F2) = 0.128

  • S = 1.09

  • 4013 reflections

  • 223 parameters

  • H-atom parameters constrained

  • Δρmax = 0.27 e Å−3

  • Δρmin = −0.22 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C5—H5B⋯O1i 0.99 2.51 3.303 (3) 137
C11—H11A⋯O1ii 0.98 2.57 3.320 (3) 133
Symmetry codes: (i) -x+2, -y, -z+2; (ii) [x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}].

Data collection: CrystalClear (Rigaku, 2007[Rigaku (2007). CrystalClear. Rigaku Corporation, Tokyo, Japan.]); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information


Comment top

As part of our ongoing studies of heterocycles (Guo, 2011), herein we report the structure of the title compound.

In the molecule (Fig. 1), all bond lengths and angles are within normal ranges.The atoms N1, N2, C1, C2, C3, C4 and C6 lie in a plan(p1), with a maximum deviation of 0.0100 (15)Å; atoms N3, C13, O3, O4, and C14 lie in a plan(p2) too, the maximum deviation is 0.0552 (12)Å. The dihedral angle between p1 and p2 is 75.44 (5)°.

Related literature top

For a related structure and background references to heterocycles as pharmaceuticals, see: Guo (2011).

Experimental top

The title compound was synthesized with 5-tert-butyl 3-ethyl 6,7-dihydro-1H- pyrazolo[4,3-c]pyridine-3,5(4H)- dicarboxylate (1 eq), NaH (2.5 eq) and 2-bromopropane (1.2 eq) in THF at 273 K to room temperature. Single crystals of the compound suitable for X-ray measurements were obtained by recrystallization from ethanol at room temperature.

Refinement top

All H atoms were fixed geometrically and allowed to ride on their attached atoms, with C—H distances in the range 0.98–1.00 Å, and with Uiso(H) = 1.2Ueq(C) or Uiso(H) = 1.5Ueq(Cmethyl).

Structure description top

As part of our ongoing studies of heterocycles (Guo, 2011), herein we report the structure of the title compound.

In the molecule (Fig. 1), all bond lengths and angles are within normal ranges.The atoms N1, N2, C1, C2, C3, C4 and C6 lie in a plan(p1), with a maximum deviation of 0.0100 (15)Å; atoms N3, C13, O3, O4, and C14 lie in a plan(p2) too, the maximum deviation is 0.0552 (12)Å. The dihedral angle between p1 and p2 is 75.44 (5)°.

For a related structure and background references to heterocycles as pharmaceuticals, see: Guo (2011).

Computing details top

Data collection: CrystalClear (Rigaku, 2007); cell refinement: CrystalClear (Rigaku, 2007); data reduction: CrystalClear (Rigaku, 2007); 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: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound with displacement ellipsoids drawn at the 30% probability level.
5-tert-Butyl 3-ethyl 1-isopropyl-4,5,6,7-tetrahydro-1H- pyrazolo[4,3-c]pyridine-3,5-dicarboxylate top
Crystal data top
C17H27N3O4F(000) = 728
Mr = 337.42Dx = 1.252 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 5928 reflections
a = 13.017 (3) Åθ = 1.6–27.5°
b = 12.771 (3) ŵ = 0.09 mm1
c = 11.952 (3) ÅT = 173 K
β = 115.760 (3)°Block, colorless
V = 1789.4 (7) Å30.21 × 0.17 × 0.06 mm
Z = 4
Data collection top
Rigaku MM007-HF CCD (Saturn 724+)
diffractometer
4013 independent reflections
Radiation source: rotating anode3330 reflections with I > 2σ(I)
Confocal monochromatorRint = 0.039
ω scans at fixed χ = 45°θmax = 27.4°, θmin = 1.7°
Absorption correction: multi-scan
(CrystalClear; Rigaku, 2007)
h = 1614
Tmin = 0.981, Tmax = 0.995k = 1615
7844 measured reflectionsl = 815
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.060Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.128H-atom parameters constrained
S = 1.09 w = 1/[σ2(Fo2) + (0.0346P)2 + 1.0152P]
where P = (Fo2 + 2Fc2)/3
4013 reflections(Δ/σ)max = 0.001
223 parametersΔρmax = 0.27 e Å3
0 restraintsΔρmin = 0.22 e Å3
Crystal data top
C17H27N3O4V = 1789.4 (7) Å3
Mr = 337.42Z = 4
Monoclinic, P21/cMo Kα radiation
a = 13.017 (3) ŵ = 0.09 mm1
b = 12.771 (3) ÅT = 173 K
c = 11.952 (3) Å0.21 × 0.17 × 0.06 mm
β = 115.760 (3)°
Data collection top
Rigaku MM007-HF CCD (Saturn 724+)
diffractometer
4013 independent reflections
Absorption correction: multi-scan
(CrystalClear; Rigaku, 2007)
3330 reflections with I > 2σ(I)
Tmin = 0.981, Tmax = 0.995Rint = 0.039
7844 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0600 restraints
wR(F2) = 0.128H-atom parameters constrained
S = 1.09Δρmax = 0.27 e Å3
4013 reflectionsΔρmin = 0.22 e Å3
223 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
xyzUiso*/Ueq
O10.89479 (12)0.21624 (10)0.88381 (12)0.0305 (3)
O20.83497 (11)0.09119 (10)0.73679 (11)0.0270 (3)
O30.59568 (12)0.19414 (12)0.66795 (13)0.0379 (4)
O40.62019 (11)0.32250 (10)0.80972 (12)0.0272 (3)
N10.86219 (13)0.02179 (11)1.09856 (13)0.0214 (3)
N20.87328 (12)0.06944 (11)1.04856 (13)0.0208 (3)
N30.77214 (13)0.23478 (12)0.81927 (14)0.0231 (3)
C10.86041 (14)0.04334 (13)0.93459 (16)0.0191 (4)
C20.83954 (14)0.06483 (14)0.91134 (16)0.0194 (4)
C30.84147 (14)0.10378 (14)1.01911 (16)0.0202 (4)
C40.82646 (16)0.21603 (14)1.04464 (17)0.0236 (4)
H4A0.75070.22671.04360.028*
H4B0.88590.23691.12720.028*
C50.83677 (16)0.28141 (14)0.94246 (17)0.0241 (4)
H5B0.91810.28690.95950.029*
H5A0.80800.35300.94330.029*
C60.82002 (16)0.13484 (14)0.80231 (17)0.0245 (4)
H6A0.76650.10100.72410.029*
H6B0.89300.14740.79740.029*
C70.86696 (14)0.12674 (14)0.85268 (16)0.0206 (4)
C80.83558 (18)0.16686 (16)0.64603 (17)0.0307 (4)
H8B0.91460.17950.65750.037*
H8A0.80280.23420.65590.037*
C90.7652 (2)0.12184 (19)0.51993 (18)0.0409 (5)
H9B0.76950.16780.45650.061*
H9A0.68560.11590.50670.061*
H9C0.79430.05230.51410.061*
C100.85336 (16)0.02244 (14)1.21705 (16)0.0241 (4)
H100.86390.09621.24820.029*
C110.94661 (17)0.04410 (16)1.31347 (17)0.0298 (4)
H11B1.02110.02091.32110.045*
H11C0.94410.03661.39390.045*
H11A0.93480.11771.28770.045*
C120.73472 (17)0.01270 (18)1.19462 (19)0.0365 (5)
H12B0.72290.08531.16520.055*
H12C0.72670.00791.27230.055*
H12A0.67790.03241.13180.055*
C130.65564 (16)0.24563 (15)0.75820 (17)0.0246 (4)
C140.49694 (16)0.34246 (16)0.76793 (18)0.0293 (4)
C150.49744 (19)0.43108 (18)0.8521 (2)0.0433 (6)
H15A0.41870.45060.83300.065*
H15C0.53680.40850.93890.065*
H15B0.53710.49160.83890.065*
C160.44174 (18)0.3756 (2)0.6327 (2)0.0434 (6)
H16B0.36280.39710.60940.065*
H16C0.48430.43450.62070.065*
H16A0.44250.31670.58050.065*
C170.44277 (19)0.24554 (19)0.7929 (2)0.0410 (5)
H17A0.44870.18720.74280.062*
H17C0.48230.22730.88110.062*
H17B0.36220.25950.77080.062*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0424 (8)0.0206 (7)0.0280 (7)0.0067 (6)0.0148 (6)0.0004 (5)
O20.0420 (8)0.0206 (7)0.0205 (6)0.0026 (6)0.0154 (6)0.0015 (5)
O30.0346 (8)0.0423 (9)0.0303 (8)0.0006 (7)0.0079 (7)0.0120 (7)
O40.0233 (7)0.0266 (7)0.0301 (7)0.0030 (5)0.0099 (6)0.0028 (6)
N10.0283 (8)0.0172 (7)0.0201 (7)0.0012 (6)0.0119 (7)0.0001 (6)
N20.0246 (8)0.0177 (7)0.0211 (7)0.0008 (6)0.0108 (6)0.0007 (6)
N30.0275 (8)0.0192 (7)0.0226 (8)0.0042 (6)0.0110 (7)0.0027 (6)
C10.0179 (8)0.0192 (9)0.0202 (8)0.0008 (7)0.0085 (7)0.0001 (7)
C20.0199 (8)0.0194 (9)0.0198 (8)0.0022 (7)0.0094 (7)0.0015 (7)
C30.0215 (9)0.0183 (9)0.0209 (8)0.0013 (7)0.0092 (7)0.0012 (7)
C40.0294 (10)0.0199 (9)0.0219 (9)0.0032 (8)0.0114 (8)0.0010 (7)
C50.0263 (9)0.0193 (9)0.0248 (9)0.0005 (7)0.0093 (8)0.0005 (7)
C60.0340 (10)0.0205 (9)0.0233 (9)0.0065 (8)0.0164 (8)0.0037 (7)
C70.0191 (8)0.0204 (9)0.0225 (9)0.0005 (7)0.0093 (7)0.0022 (7)
C80.0410 (12)0.0279 (10)0.0263 (10)0.0007 (9)0.0176 (9)0.0068 (8)
C90.0554 (14)0.0414 (13)0.0237 (10)0.0036 (11)0.0152 (10)0.0064 (9)
C100.0354 (10)0.0223 (9)0.0177 (8)0.0003 (8)0.0143 (8)0.0017 (7)
C110.0368 (11)0.0302 (11)0.0210 (9)0.0016 (9)0.0113 (9)0.0022 (8)
C120.0343 (11)0.0490 (13)0.0320 (11)0.0023 (10)0.0198 (9)0.0007 (10)
C130.0285 (10)0.0229 (9)0.0231 (9)0.0023 (8)0.0118 (8)0.0022 (8)
C140.0223 (9)0.0337 (11)0.0321 (10)0.0019 (8)0.0121 (8)0.0006 (9)
C150.0356 (12)0.0398 (13)0.0555 (15)0.0079 (10)0.0207 (11)0.0071 (11)
C160.0289 (11)0.0602 (16)0.0395 (12)0.0135 (11)0.0133 (10)0.0149 (11)
C170.0385 (12)0.0445 (13)0.0453 (13)0.0071 (10)0.0231 (11)0.0003 (11)
Geometric parameters (Å, º) top
O1—C71.208 (2)C8—H8B0.9900
O2—C71.340 (2)C8—H8A0.9900
O2—C81.455 (2)C9—H9B0.9800
O3—C131.214 (2)C9—H9A0.9800
O4—C131.343 (2)C9—H9C0.9800
O4—C141.480 (2)C10—C121.516 (3)
N1—N21.345 (2)C10—C111.519 (3)
N1—C31.360 (2)C10—H101.0000
N1—C101.470 (2)C11—H11B0.9800
N2—C11.340 (2)C11—H11C0.9800
N3—C131.375 (2)C11—H11A0.9800
N3—C51.468 (2)C12—H12B0.9800
N3—C61.472 (2)C12—H12C0.9800
C1—C21.412 (2)C12—H12A0.9800
C1—C71.474 (2)C14—C151.512 (3)
C2—C31.371 (2)C14—C161.516 (3)
C2—C61.508 (2)C14—C171.517 (3)
C3—C41.496 (2)C15—H15A0.9800
C4—C51.533 (2)C15—H15C0.9800
C4—H4A0.9900C15—H15B0.9800
C4—H4B0.9900C16—H16B0.9800
C5—H5B0.9900C16—H16C0.9800
C5—H5A0.9900C16—H16A0.9800
C6—H6A0.9900C17—H17A0.9800
C6—H6B0.9900C17—H17C0.9800
C8—C91.497 (3)C17—H17B0.9800
C7—O2—C8116.44 (14)C8—C9—H9C109.5
C13—O4—C14120.61 (14)H9B—C9—H9C109.5
N2—N1—C3112.56 (14)H9A—C9—H9C109.5
N2—N1—C10120.08 (14)N1—C10—C12109.16 (15)
C3—N1—C10126.43 (15)N1—C10—C11110.89 (15)
C1—N2—N1104.24 (14)C12—C10—C11112.66 (17)
C13—N3—C5120.72 (15)N1—C10—H10108.0
C13—N3—C6116.71 (15)C12—C10—H10108.0
C5—N3—C6113.42 (14)C11—C10—H10108.0
N2—C1—C2111.82 (15)C10—C11—H11B109.5
N2—C1—C7118.53 (15)C10—C11—H11C109.5
C2—C1—C7129.64 (16)H11B—C11—H11C109.5
C3—C2—C1104.29 (15)C10—C11—H11A109.5
C3—C2—C6121.62 (16)H11B—C11—H11A109.5
C1—C2—C6134.09 (16)H11C—C11—H11A109.5
N1—C3—C2107.09 (15)C10—C12—H12B109.5
N1—C3—C4126.83 (15)C10—C12—H12C109.5
C2—C3—C4126.07 (16)H12B—C12—H12C109.5
C3—C4—C5107.16 (14)C10—C12—H12A109.5
C3—C4—H4A110.3H12B—C12—H12A109.5
C5—C4—H4A110.3H12C—C12—H12A109.5
C3—C4—H4B110.3O3—C13—O4125.96 (18)
C5—C4—H4B110.3O3—C13—N3123.52 (17)
H4A—C4—H4B108.5O4—C13—N3110.48 (15)
N3—C5—C4111.58 (15)O4—C14—C15102.34 (15)
N3—C5—H5B109.3O4—C14—C16110.48 (15)
C4—C5—H5B109.3C15—C14—C16111.31 (19)
N3—C5—H5A109.3O4—C14—C17108.74 (16)
C4—C5—H5A109.3C15—C14—C17110.36 (18)
H5B—C5—H5A108.0C16—C14—C17113.07 (18)
N3—C6—C2108.50 (14)C14—C15—H15A109.5
N3—C6—H6A110.0C14—C15—H15C109.5
C2—C6—H6A110.0H15A—C15—H15C109.5
N3—C6—H6B110.0C14—C15—H15B109.5
C2—C6—H6B110.0H15A—C15—H15B109.5
H6A—C6—H6B108.4H15C—C15—H15B109.5
O1—C7—O2123.77 (16)C14—C16—H16B109.5
O1—C7—C1125.12 (17)C14—C16—H16C109.5
O2—C7—C1111.09 (15)H16B—C16—H16C109.5
O2—C8—C9107.22 (16)C14—C16—H16A109.5
O2—C8—H8B110.3H16B—C16—H16A109.5
C9—C8—H8B110.3H16C—C16—H16A109.5
O2—C8—H8A110.3C14—C17—H17A109.5
C9—C8—H8A110.3C14—C17—H17C109.5
H8B—C8—H8A108.5H17A—C17—H17C109.5
C8—C9—H9B109.5C14—C17—H17B109.5
C8—C9—H9A109.5H17A—C17—H17B109.5
H9B—C9—H9A109.5H17C—C17—H17B109.5
C3—N1—N2—C10.73 (19)C3—C2—C6—N316.5 (2)
C10—N1—N2—C1170.41 (15)C1—C2—C6—N3164.66 (18)
N1—N2—C1—C20.77 (19)C8—O2—C7—O10.4 (3)
N1—N2—C1—C7179.55 (14)C8—O2—C7—C1178.84 (15)
N2—C1—C2—C30.5 (2)N2—C1—C7—O18.1 (3)
C7—C1—C2—C3179.14 (17)C2—C1—C7—O1173.39 (18)
N2—C1—C2—C6179.51 (18)N2—C1—C7—O2170.33 (15)
C7—C1—C2—C61.9 (3)C2—C1—C7—O28.2 (3)
N2—N1—C3—C20.4 (2)C7—O2—C8—C9163.00 (16)
C10—N1—C3—C2169.31 (16)N2—N1—C10—C1275.7 (2)
N2—N1—C3—C4179.00 (16)C3—N1—C10—C1292.4 (2)
C10—N1—C3—C412.1 (3)N2—N1—C10—C1149.0 (2)
C1—C2—C3—N10.07 (18)C3—N1—C10—C11142.90 (17)
C6—C2—C3—N1179.20 (15)C14—O4—C13—O38.2 (3)
C1—C2—C3—C4178.52 (17)C14—O4—C13—N3174.12 (15)
C6—C2—C3—C40.6 (3)C5—N3—C13—O3166.25 (18)
N1—C3—C4—C5165.31 (16)C6—N3—C13—O321.5 (3)
C2—C3—C4—C513.0 (2)C5—N3—C13—O416.0 (2)
C13—N3—C5—C477.8 (2)C6—N3—C13—O4160.74 (14)
C6—N3—C5—C467.98 (19)C13—O4—C14—C15178.30 (17)
C3—C4—C5—N344.5 (2)C13—O4—C14—C1663.1 (2)
C13—N3—C6—C297.36 (18)C13—O4—C14—C1761.5 (2)
C5—N3—C6—C249.90 (19)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C5—H5B···O1i0.992.513.303 (3)137
C11—H11A···O1ii0.982.573.320 (3)133
Symmetry codes: (i) x+2, y, z+2; (ii) x, y+1/2, z+1/2.

Experimental details

Crystal data
Chemical formulaC17H27N3O4
Mr337.42
Crystal system, space groupMonoclinic, P21/c
Temperature (K)173
a, b, c (Å)13.017 (3), 12.771 (3), 11.952 (3)
β (°) 115.760 (3)
V3)1789.4 (7)
Z4
Radiation typeMo Kα
µ (mm1)0.09
Crystal size (mm)0.21 × 0.17 × 0.06
Data collection
DiffractometerRigaku MM007-HF CCD (Saturn 724+)
Absorption correctionMulti-scan
(CrystalClear; Rigaku, 2007)
Tmin, Tmax0.981, 0.995
No. of measured, independent and
observed [I > 2σ(I)] reflections
7844, 4013, 3330
Rint0.039
(sin θ/λ)max1)0.648
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.060, 0.128, 1.09
No. of reflections4013
No. of parameters223
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.27, 0.22

Computer programs: CrystalClear (Rigaku, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C5—H5B···O1i0.992.513.303 (3)137
C11—H11A···O1ii0.982.573.320 (3)133
Symmetry codes: (i) x+2, y, z+2; (ii) x, y+1/2, z+1/2.
 

Acknowledgements

The author would like to thank Shandong Provincial Natural Science Foundation, China (Y2008B29) and Yuandu Scholar of Weifang City.

References

First citationGuo, H.-M. (2011). Acta Cryst. E67, o2516.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationRigaku (2007). CrystalClear. Rigaku Corporation, Tokyo, Japan.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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