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Acta Crystallogr Sect E Struct Rep Online. 2010 July 1; 66(Pt 7): o1750.
Published online 2010 June 23. doi:  10.1107/S1600536810023433
PMCID: PMC3006808

tert-Butyl 2-[4-(2-{4-[(tert-butoxycar­bonyl)methoxy]-3-methylphenyl}-2-propyl)-2-methylphenoxy]acetate

Abstract

In the mol­ecule of the title compound, C29H40O6, the carbon atom belonging to the propyl chain is connected to two aromatic rings that open up the Car­yl—C—Car­yl angle to 111.5 (1)°. The four-atom –O–CH2–C(=O)–O– linkage between the aromatic ring and the tert-butyl group assumes a (−)anti-periplanar conformation for one substituent and a (−)syn-periplanar conformation for the other substituent; the O–C–C–O torsion angles are −173.7 (2) and −10.2 (3)°.

Related literature

For the crystal structure of a related V-shaped mol­ecule, see: Shah et al. (2010 [triangle]).

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Object name is e-66-o1750-scheme1.jpg

Experimental

Crystal data

  • C29H40O6
  • M r = 484.61
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-o1750-efi1.jpg
  • a = 8.3154 (6) Å
  • b = 12.5589 (8) Å
  • c = 13.9410 (9) Å
  • α = 101.782 (1)°
  • β = 97.529 (1)°
  • γ = 94.156 (1)°
  • V = 1405.52 (16) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 0.08 mm−1
  • T = 293 K
  • 0.45 × 0.35 × 0.30 mm

Data collection

  • Bruker SMART APEX diffractometer
  • 13784 measured reflections
  • 6428 independent reflections
  • 4482 reflections with I > 2σ(I)
  • R int = 0.021

Refinement

  • R[F 2 > 2σ(F 2)] = 0.060
  • wR(F 2) = 0.184
  • S = 1.03
  • 6428 reflections
  • 318 parameters
  • H-atom parameters constrained
  • Δρmax = 0.35 e Å−3
  • Δρmin = −0.19 e Å−3

Data collection: SMART (Bruker, 2002 [triangle]); cell refinement: SAINT (Bruker, 2002 [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: X-SEED (Barbour, 2001 [triangle]); software used to prepare material for publication: publCIF (Westrip, 2010 [triangle]).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810023433/ci5103sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810023433/ci5103Isup2.hkl

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

Acknowledgments

The authors thank the Higher Education Commission of Pakistan and the University of Malaya for supporting this study.

supplementary crystallographic information

Comment

We are interested in the solid-state structures of V-shaped molecules. A recent study reported the crystal structure of 9,9-bis[4-(tert-butoxycarbonylmethyloxy)phenyl]fluorene, a compound used as dissolution inhibitor for protecting photosensitive poly(benzoxazole)s (Shah et al., 2010). The V shape induced by the fluorenyl portion is now replaced by an i-propyl unit to furnish a similarly shaped molecule (Scheme I, Fig. 1). In the title molecule, the carbon atom belonging to the propyl chain is connected to two aromatic rings that open up the CarylC–Caryl to 111.5 (1)°. The four-atom –O–CH2–C(═O)–O– chain between the aromatic ring and the tert-butyl group assumes a W shape for one substituent and a U shape for the other substituent [O–C–C–O torsion angle -173.7 (2)° and -10.2 (3)°].

Experimental

2,2-Bis(4-hydroxy-3-methylphenyl)propane (0.50 g) and potassium carbonate (0.85 g) were placed in acetone (25 ml) and to this was added tert-butyl bromoacetate (0.75 ml, 5 mmol). The mixture was stirred at room temperature for 3 h. The solvent was evaporated under reduced pressure and the residue was dissolved in a mixture of water (50 ml) and dichloromethane (50 ml). The aqueous layer was extracted three times with dichloromethane. The combined organic phases were evaporated under reduced pressure and the solid material was recrystallized from n-hexane. Colourless crystals were obtained in 80% yield.

Refinement

H atoms were placed in calculated positions [C–H = 0.93–0.97 Å] and were included in the refinement in the riding model approximation, with Uiso(H) = 1.2–1.5Ueq(C).

Figures

Fig. 1.
Displacement ellipsoid plot (Barbour, 2001) of C29H40O6 at the 50% probability level. H atoms are drawn as spheres of arbitrary radius.

Crystal data

C29H40O6Z = 2
Mr = 484.61F(000) = 524
Triclinic, P1Dx = 1.145 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.3154 (6) ÅCell parameters from 4014 reflections
b = 12.5589 (8) Åθ = 2.5–27.3°
c = 13.9410 (9) ŵ = 0.08 mm1
α = 101.782 (1)°T = 293 K
β = 97.529 (1)°Block, colourless
γ = 94.156 (1)°0.45 × 0.35 × 0.30 mm
V = 1405.52 (16) Å3

Data collection

Bruker SMART APEX diffractometer4482 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.021
graphiteθmax = 27.5°, θmin = 1.7°
ω scansh = −10→10
13784 measured reflectionsk = −16→14
6428 independent reflectionsl = −18→17

Refinement

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) = 0.184H-atom parameters constrained
S = 1.03w = 1/[σ2(Fo2) + (0.0989P)2 + 0.2549P] where P = (Fo2 + 2Fc2)/3
6428 reflections(Δ/σ)max = 0.001
318 parametersΔρmax = 0.35 e Å3
0 restraintsΔρmin = −0.19 e Å3

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

xyzUiso*/Ueq
O10.54867 (16)0.16145 (12)0.44990 (9)0.0584 (4)
O20.28231 (18)0.17998 (13)0.40617 (11)0.0644 (4)
O30.22035 (16)0.13010 (10)0.58548 (10)0.0537 (3)
O40.13940 (17)0.83903 (11)1.01874 (10)0.0608 (4)
O50.4354 (2)0.79162 (18)1.21064 (11)0.0891 (6)
O60.43525 (16)0.77133 (14)1.04833 (10)0.0665 (4)
C10.6069 (3)0.17993 (18)0.35761 (14)0.0571 (5)
C20.7872 (3)0.1715 (3)0.3802 (2)0.1093 (12)
H2A0.83370.22750.43690.164*
H2B0.83840.18080.32420.164*
H2C0.80440.10100.39390.164*
C30.5730 (4)0.29242 (19)0.34262 (19)0.0811 (7)
H3A0.62490.34650.39940.122*
H3B0.45750.29720.33440.122*
H3C0.61500.30510.28460.122*
C40.5265 (4)0.0919 (2)0.27129 (18)0.0882 (8)
H4A0.41080.09610.26250.132*
H4B0.54860.02160.28390.132*
H4C0.56850.10160.21240.132*
C50.3936 (2)0.16414 (14)0.46314 (13)0.0459 (4)
C60.3813 (2)0.14131 (16)0.56480 (14)0.0516 (4)
H6A0.43070.07470.57000.062*
H6B0.44340.20050.61460.062*
C70.1432 (2)0.22212 (13)0.61535 (12)0.0424 (4)
C80.2100 (2)0.32846 (15)0.62278 (14)0.0501 (4)
H80.31460.34180.60820.060*
C90.1196 (2)0.41480 (14)0.65211 (14)0.0506 (4)
H90.16610.48600.65850.061*
C10−0.0379 (2)0.39793 (13)0.67218 (12)0.0429 (4)
C11−0.0997 (2)0.29071 (14)0.66524 (12)0.0432 (4)
H11−0.20450.27750.67950.052*
C12−0.0121 (2)0.20183 (13)0.63788 (12)0.0423 (4)
C13−0.0854 (3)0.08640 (15)0.63031 (16)0.0593 (5)
H13A−0.19550.08750.64410.089*
H13B−0.02230.05400.67740.089*
H13C−0.08510.04430.56460.089*
C14−0.1407 (2)0.49513 (14)0.69162 (14)0.0480 (4)
C15−0.3066 (2)0.46110 (18)0.7189 (2)0.0755 (7)
H15A−0.36410.40360.66690.113*
H15B−0.36910.52280.72740.113*
H15C−0.29040.43560.77960.113*
C16−0.1702 (3)0.53592 (18)0.59406 (15)0.0711 (7)
H16A−0.06730.55580.57490.107*
H16B−0.23090.59850.60370.107*
H16C−0.23080.47880.54290.107*
C17−0.0548 (2)0.58614 (13)0.77766 (12)0.0403 (4)
C18−0.0610 (2)0.69584 (13)0.77638 (12)0.0402 (4)
H18−0.11100.71430.71920.048*
C190.0042 (2)0.77945 (13)0.85692 (12)0.0420 (4)
C200.0800 (2)0.75110 (14)0.94170 (13)0.0445 (4)
C210.0898 (2)0.64272 (16)0.94550 (14)0.0522 (4)
H210.14150.62431.00230.063*
C220.0220 (2)0.56143 (15)0.86392 (14)0.0494 (4)
H220.02810.48860.86710.059*
C23−0.0095 (3)0.89746 (16)0.85277 (17)0.0642 (6)
H23A0.09770.93580.86330.096*
H23B−0.06960.93030.90340.096*
H23C−0.06510.90150.78900.096*
C240.1975 (2)0.8205 (2)1.11273 (14)0.0632 (6)
H24A0.12630.76181.12510.076*
H24B0.18810.88571.16190.076*
C250.3708 (2)0.79182 (16)1.12921 (13)0.0527 (5)
C260.6032 (2)0.7409 (2)1.04549 (17)0.0702 (6)
C270.6246 (5)0.6415 (3)1.0903 (3)0.1357 (14)
H27A0.61500.66021.15950.203*
H27B0.73030.61781.08270.203*
H27C0.54190.58361.05720.203*
C280.7205 (4)0.8347 (3)1.1020 (3)0.1313 (15)
H28A0.70170.89821.07540.197*
H28B0.82990.81721.09670.197*
H28C0.70550.84931.17040.197*
C290.6096 (4)0.7084 (4)0.9371 (2)0.1321 (15)
H29A0.59310.77010.90730.198*
H29B0.52570.65020.90720.198*
H29C0.71420.68420.92700.198*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.0552 (8)0.0840 (10)0.0451 (7)0.0226 (7)0.0167 (6)0.0235 (7)
O20.0593 (8)0.0816 (10)0.0560 (8)0.0185 (7)0.0039 (7)0.0224 (7)
O30.0603 (8)0.0434 (7)0.0634 (8)0.0169 (6)0.0273 (6)0.0100 (6)
O40.0636 (8)0.0574 (8)0.0506 (8)0.0147 (6)−0.0056 (6)−0.0076 (6)
O50.0735 (11)0.1484 (18)0.0461 (9)0.0218 (11)0.0038 (7)0.0219 (9)
O60.0487 (8)0.1064 (12)0.0437 (7)0.0157 (7)0.0103 (6)0.0098 (7)
C10.0673 (12)0.0676 (13)0.0446 (10)0.0186 (10)0.0208 (9)0.0193 (9)
C20.0730 (17)0.195 (4)0.093 (2)0.048 (2)0.0443 (15)0.075 (2)
C30.113 (2)0.0603 (14)0.0764 (16)0.0089 (13)0.0251 (14)0.0213 (12)
C40.136 (2)0.0705 (15)0.0585 (14)0.0123 (15)0.0343 (15)0.0028 (11)
C50.0526 (10)0.0408 (9)0.0452 (9)0.0152 (7)0.0102 (8)0.0055 (7)
C60.0563 (11)0.0560 (11)0.0490 (10)0.0241 (9)0.0171 (8)0.0141 (8)
C70.0503 (9)0.0407 (9)0.0375 (8)0.0122 (7)0.0120 (7)0.0055 (7)
C80.0454 (9)0.0462 (10)0.0595 (11)0.0042 (8)0.0177 (8)0.0074 (8)
C90.0538 (10)0.0344 (9)0.0622 (11)0.0019 (7)0.0144 (8)0.0049 (8)
C100.0462 (9)0.0370 (8)0.0426 (9)0.0070 (7)0.0067 (7)0.0004 (7)
C110.0430 (9)0.0422 (9)0.0429 (9)0.0042 (7)0.0113 (7)0.0029 (7)
C120.0540 (10)0.0355 (8)0.0372 (8)0.0059 (7)0.0112 (7)0.0041 (6)
C130.0721 (13)0.0401 (10)0.0686 (13)0.0044 (9)0.0302 (10)0.0066 (9)
C140.0489 (10)0.0385 (9)0.0524 (10)0.0110 (7)0.0031 (8)0.0010 (7)
C150.0450 (11)0.0517 (12)0.119 (2)0.0112 (9)0.0138 (11)−0.0087 (12)
C160.0976 (17)0.0548 (12)0.0504 (11)0.0289 (11)−0.0129 (11)−0.0050 (9)
C170.0419 (8)0.0387 (8)0.0405 (8)0.0093 (7)0.0107 (7)0.0048 (7)
C180.0458 (9)0.0396 (9)0.0369 (8)0.0100 (7)0.0101 (7)0.0079 (6)
C190.0441 (9)0.0388 (9)0.0443 (9)0.0086 (7)0.0130 (7)0.0061 (7)
C200.0413 (9)0.0461 (9)0.0428 (9)0.0090 (7)0.0075 (7)−0.0005 (7)
C210.0564 (11)0.0567 (11)0.0432 (9)0.0166 (8)0.0007 (8)0.0105 (8)
C220.0586 (11)0.0391 (9)0.0525 (10)0.0141 (8)0.0060 (8)0.0129 (8)
C230.0833 (15)0.0417 (10)0.0646 (13)0.0103 (10)0.0068 (11)0.0058 (9)
C240.0547 (11)0.0802 (15)0.0449 (10)0.0143 (10)0.0049 (8)−0.0102 (9)
C250.0516 (10)0.0627 (12)0.0382 (9)0.0016 (8)0.0045 (8)0.0010 (8)
C260.0450 (11)0.0988 (18)0.0643 (13)0.0143 (11)0.0131 (9)0.0065 (12)
C270.140 (3)0.116 (3)0.163 (4)0.069 (2)0.040 (3)0.029 (3)
C280.0605 (16)0.132 (3)0.174 (4)−0.0194 (17)0.0303 (19)−0.027 (3)
C290.087 (2)0.228 (5)0.081 (2)0.045 (2)0.0380 (17)0.007 (2)

Geometric parameters (Å, °)

O1—C51.328 (2)C13—H13C0.96
O1—C11.488 (2)C14—C151.533 (3)
O2—C51.194 (2)C14—C171.534 (2)
O3—C71.379 (2)C14—C161.545 (3)
O3—C61.409 (2)C15—H15A0.96
O4—C201.384 (2)C15—H15B0.96
O4—C241.407 (3)C15—H15C0.96
O5—C251.191 (2)C16—H16A0.96
O6—C251.298 (2)C16—H16B0.96
O6—C261.478 (2)C16—H16C0.96
C1—C41.502 (3)C17—C181.386 (2)
C1—C21.507 (3)C17—C221.389 (2)
C1—C31.511 (3)C18—C191.391 (2)
C2—H2A0.96C18—H180.93
C2—H2B0.96C19—C201.389 (2)
C2—H2C0.96C19—C231.507 (3)
C3—H3A0.96C20—C211.381 (3)
C3—H3B0.96C21—C221.389 (3)
C3—H3C0.96C21—H210.93
C4—H4A0.96C22—H220.93
C4—H4B0.96C23—H23A0.96
C4—H4C0.96C23—H23B0.96
C5—C61.517 (3)C23—H23C0.96
C6—H6A0.97C24—C251.510 (3)
C6—H6B0.97C24—H24A0.97
C7—C121.387 (2)C24—H24B0.97
C7—C81.387 (3)C26—C281.488 (4)
C8—C91.388 (3)C26—C291.492 (4)
C8—H80.93C26—C271.517 (5)
C9—C101.385 (3)C27—H27A0.96
C9—H90.93C27—H27B0.96
C10—C111.386 (2)C27—H27C0.96
C10—C141.540 (2)C28—H28A0.96
C11—C121.392 (2)C28—H28B0.96
C11—H110.93C28—H28C0.96
C12—C131.509 (2)C29—H29A0.96
C13—H13A0.96C29—H29B0.96
C13—H13B0.96C29—H29C0.96
C5—O1—C1122.52 (14)C14—C15—H15B109.5
C7—O3—C6119.71 (14)H15A—C15—H15B109.5
C20—O4—C24119.61 (16)C14—C15—H15C109.5
C25—O6—C26123.23 (16)H15A—C15—H15C109.5
O1—C1—C4109.56 (18)H15B—C15—H15C109.5
O1—C1—C2101.98 (16)C14—C16—H16A109.5
C4—C1—C2111.8 (2)C14—C16—H16B109.5
O1—C1—C3109.83 (17)H16A—C16—H16B109.5
C4—C1—C3111.7 (2)C14—C16—H16C109.5
C2—C1—C3111.5 (2)H16A—C16—H16C109.5
C1—C2—H2A109.5H16B—C16—H16C109.5
C1—C2—H2B109.5C18—C17—C22117.09 (15)
H2A—C2—H2B109.5C18—C17—C14121.98 (15)
C1—C2—H2C109.5C22—C17—C14120.75 (15)
H2A—C2—H2C109.5C17—C18—C19122.83 (15)
H2B—C2—H2C109.5C17—C18—H18118.6
C1—C3—H3A109.5C19—C18—H18118.6
C1—C3—H3B109.5C20—C19—C18118.19 (15)
H3A—C3—H3B109.5C20—C19—C23120.99 (16)
C1—C3—H3C109.5C18—C19—C23120.81 (16)
H3A—C3—H3C109.5C21—C20—O4124.86 (16)
H3B—C3—H3C109.5C21—C20—C19120.66 (16)
C1—C4—H4A109.5O4—C20—C19114.47 (15)
C1—C4—H4B109.5C20—C21—C22119.52 (16)
H4A—C4—H4B109.5C20—C21—H21120.2
C1—C4—H4C109.5C22—C21—H21120.2
H4A—C4—H4C109.5C21—C22—C17121.70 (16)
H4B—C4—H4C109.5C21—C22—H22119.2
O2—C5—O1127.28 (17)C17—C22—H22119.2
O2—C5—C6125.41 (17)C19—C23—H23A109.5
O1—C5—C6107.31 (15)C19—C23—H23B109.5
O3—C6—C5113.92 (15)H23A—C23—H23B109.5
O3—C6—H6A108.8C19—C23—H23C109.5
C5—C6—H6A108.8H23A—C23—H23C109.5
O3—C6—H6B108.8H23B—C23—H23C109.5
C5—C6—H6B108.8O4—C24—C25116.98 (17)
H6A—C6—H6B107.7O4—C24—H24A108.1
O3—C7—C12114.91 (15)C25—C24—H24A108.1
O3—C7—C8124.60 (16)O4—C24—H24B108.1
C12—C7—C8120.48 (15)C25—C24—H24B108.1
C7—C8—C9119.50 (17)H24A—C24—H24B107.3
C7—C8—H8120.2O5—C25—O6126.65 (19)
C9—C8—H8120.2O5—C25—C24120.14 (18)
C10—C9—C8121.84 (16)O6—C25—C24113.20 (16)
C10—C9—H9119.1O6—C26—C28109.1 (2)
C8—C9—H9119.1O6—C26—C29102.79 (19)
C9—C10—C11116.96 (15)C28—C26—C29116.1 (3)
C9—C10—C14119.77 (15)O6—C26—C27109.7 (2)
C11—C10—C14123.03 (15)C28—C26—C27110.2 (3)
C10—C11—C12123.05 (16)C29—C26—C27108.5 (3)
C10—C11—H11118.5C26—C27—H27A109.5
C12—C11—H11118.5C26—C27—H27B109.5
C7—C12—C11118.11 (15)H27A—C27—H27B109.5
C7—C12—C13120.80 (15)C26—C27—H27C109.5
C11—C12—C13121.08 (16)H27A—C27—H27C109.5
C12—C13—H13A109.5H27B—C27—H27C109.5
C12—C13—H13B109.5C26—C28—H28A109.5
H13A—C13—H13B109.5C26—C28—H28B109.5
C12—C13—H13C109.5H28A—C28—H28B109.5
H13A—C13—H13C109.5C26—C28—H28C109.5
H13B—C13—H13C109.5H28A—C28—H28C109.5
C15—C14—C17106.90 (16)H28B—C28—H28C109.5
C15—C14—C10111.80 (15)C26—C29—H29A109.5
C17—C14—C10111.47 (14)C26—C29—H29B109.5
C15—C14—C16108.36 (18)H29A—C29—H29B109.5
C17—C14—C16111.53 (15)C26—C29—H29C109.5
C10—C14—C16106.79 (15)H29A—C29—H29C109.5
C14—C15—H15A109.5H29B—C29—H29C109.5
C5—O1—C1—C4−62.9 (2)C15—C14—C17—C18−95.7 (2)
C5—O1—C1—C2178.6 (2)C10—C14—C17—C18141.89 (16)
C5—O1—C1—C360.2 (3)C16—C14—C17—C1822.6 (2)
C1—O1—C5—O20.6 (3)C15—C14—C17—C2279.1 (2)
C1—O1—C5—C6179.73 (16)C10—C14—C17—C22−43.3 (2)
C7—O3—C6—C5−80.1 (2)C16—C14—C17—C22−162.58 (17)
O2—C5—C6—O35.4 (3)C22—C17—C18—C19−0.6 (3)
O1—C5—C6—O3−173.69 (15)C14—C17—C18—C19174.44 (15)
C6—O3—C7—C12−177.31 (15)C17—C18—C19—C200.6 (3)
C6—O3—C7—C83.2 (3)C17—C18—C19—C23−178.41 (17)
O3—C7—C8—C9178.89 (17)C24—O4—C20—C21−8.0 (3)
C12—C7—C8—C9−0.6 (3)C24—O4—C20—C19170.98 (16)
C7—C8—C9—C10−1.5 (3)C18—C19—C20—C210.0 (3)
C8—C9—C10—C112.3 (3)C23—C19—C20—C21178.97 (18)
C8—C9—C10—C14−172.32 (17)C18—C19—C20—O4−179.11 (15)
C9—C10—C11—C12−1.1 (3)C23—C19—C20—O4−0.1 (2)
C14—C10—C11—C12173.34 (16)O4—C20—C21—C22178.45 (17)
O3—C7—C12—C11−177.78 (14)C19—C20—C21—C22−0.5 (3)
C8—C7—C12—C111.8 (3)C20—C21—C22—C170.6 (3)
O3—C7—C12—C130.7 (2)C18—C17—C22—C210.0 (3)
C8—C7—C12—C13−179.79 (18)C14—C17—C22—C21−175.09 (17)
C10—C11—C12—C7−0.9 (3)C20—O4—C24—C2582.9 (2)
C10—C11—C12—C13−179.34 (17)C26—O6—C25—O51.7 (4)
C9—C10—C14—C15−176.28 (18)C26—O6—C25—C24−179.7 (2)
C11—C10—C14—C159.4 (3)O4—C24—C25—O5168.5 (2)
C9—C10—C14—C17−56.7 (2)O4—C24—C25—O6−10.2 (3)
C11—C10—C14—C17129.00 (18)C25—O6—C26—C28−65.1 (3)
C9—C10—C14—C1665.4 (2)C25—O6—C26—C29171.0 (3)
C11—C10—C14—C16−109.0 (2)C25—O6—C26—C2755.7 (3)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CI5103).

References

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