1,7,7-Trimethyl-3-(naphthalen-2-ylcarbon­yl)bi­cyclo­[2.2.1]heptan-2-one

Bendia, S.; Ouari, K.; Ait Ali, M.; Firdousi, L. el; Nazarenko, A.Y.

doi:10.1107/S2414314620016624

organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 5| Part 12| December 2020| x201662

https://doi.org/10.1107/S2414314620016624

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1,7,7-Trimethyl-3-(naphthalen-2-ylcarbonyl)bicyclo[2.2.1]heptan-2-one

Sabrina Bendia,^a Kamel Ouari,^a Mustapha Ait Ali,^b Larbi el Firdousi ^b and Alexander Y. Nazarenko ^c ^*

^aLaboratoire d'Electrochimie, d'Ingénierie Moléculaire et de Catalyse Rédox (LEIMCR), Faculté de Technologie, Université Ferhat Abbas-Sétif-1, Sétif, 19000 , Algeria, ^bUniversité Cadi Ayyad Faculté des Sciences Semlalia, Departement de Chimie, BP 2390, 40001, Marrakech, Morocco, and ^cChemistry Department, State University of New York, College at Buffalo, 1300 Elmwood Ave, Buffalo, NY 14222-1095, USA
^*Correspondence e-mail: nazareay@buffalostate.edu

Edited by R. J. Butcher, Howard University, USA (Received 17 December 2020; accepted 22 December 2020; online 24 December 2020)

The title compound, C₂₁H₂₂O₂, crystallizes in its keto form. The molecules are connected via weak C—H⋯O interactions, forming infinite chains perpendicular to the [001] axis.

Keywords: crystal structure; β-diketone; naphthyl; camphor.

CCDC reference: 2052026

Structure description

Chiral β-diketonato ligands are used in catalysis and spectroscopy; chiral naphthyl derivatives have recently been prepared (Clark et al., 2013 ). However, no naphthyl-substituted β-diketones were found in the Cambridge Structure Database (Groom et al., 2016 ) in November 2020.

The title compound, C₂₁H₂₂O₂, crystallizes in its keto-form (Fig. 1). The shape of both the camphor and naphthyl fragments is essentially the same as in their parent molecules.

Figure 1
Numbering scheme of the title compound with 50% probability displacement ellipsoids.

There are no strong intermolecular interactions in this structure. The molecules are connected via weak C—H⋯O bonds (Table 1), forming infinite chains perpendicular to the [001] axis (Fig. 2). The hydrogen atoms of the naphthyl ring system and atoms H9B, H9C, and H10B of the methyl groups of the camphor fragment help to assemble these chains in the crystal via van der Waals interactions.

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13—H13⋯O1ⁱ	0.95	2.57	3.296 (3)	134
C16—H16⋯O2ⁱⁱ	0.95	2.57	3.458 (3)	156
Symmetry codes: (i) $[-x+{\script{3\over 2}}, y-{\script{1\over 2}}, -z+{\script{5\over 4}}]$ ; (ii) .

Figure 2
Packing diagram of the title compound showing C—H⋯O hydrogen bonding; the view along the [001] vector, which is parallel to the 4₁ screw axis. Only one layer of molecules is shown; the screw-axis symmetry operation rotates each subsequent layer by 90° and moves by c/4.

Synthesis and crystallization

The title compound was prepared by a procedure reported earlier (Clark et al., 2013) and was purified by recrystallization from hexane solution (m.p. 399 K). Elemental analysis for C₂₁H₂₂O₂, calculated C 82.30, H 7.24; found C 82.23, H 7.15. ¹H NMR: (DMSO-d₆, δ p.p.m.): 12.50 (s, OH), 9.00–7.40 (m, H_Ar), 2.80–0.80 (m, H_Camphor); ¹³C NMR: (DMSO-d₆, δ p.p.m.): 212–194 (C=O), 135–115 (C_Ar), 64–9 (C_Camphor). UV–vis in acetonitrile (λ_max (nm), [ɛ] (l mol⁻¹ cm⁻¹)): 272 [10197], 283 [12668], 292 [10352], 325 [8294]. Single crystals were grown by slow evaporation of a methanol solution at room temperature.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2.

Table 2
Experimental details

Crystal data
Chemical formula	C₂₁H₂₂O₂
M_r	306.38
Crystal system, space group	Tetragonal, P4₁2₁2
Temperature (K)	173
a, c (Å)	9.5637 (3), 36.3395 (10)
V (Å³)	3323.8 (2)
Z	8
Radiation type	Cu Kα
μ (mm⁻¹)	0.60
Crystal size (mm)	0.41 × 0.33 × 0.17

Data collection
Diffractometer	Bruker PHOTON-100 CMOS
Absorption correction	Multi-scan (SADABS; Krause et al., 2015 )
T_min, T_max	0.922, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	27362, 3363, 3123
R_int	0.034
(sin θ/λ)_max (Å⁻¹)	0.627

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.110, 1.05
No. of reflections	3363
No. of parameters	211
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.33, −0.16
Absolute structure	Flack x determined using 1176 quotients [(I⁺)−(I⁻)]/[(I⁺)+(I⁻)] (Parsons et al., 2013 )
Absolute structure parameter	−0.04 (10)
Computer programs: APEX2 and SAINT (Bruker, 2016 ), SHELXT (Sheldrick, 2015a ), SHELXL (Sheldrick, 2015b ), OLEX2 (Dolomanov et al., 2009 ) and VESTA (Momma & Izumi, 2011 ).

Structural data

CCDC reference: 2052026

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2414314620016624/bv4034sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314620016624/bv4034Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2414314620016624/bv4034Isup3.cdx

Supporting information file. DOI: https://doi.org/10.1107/S2414314620016624/bv4034Isup4.cml

checkCIF report

Computing details top

Data collection: APEX2 (Bruker, 2016); cell refinement: SAINT (Bruker, 2016); data reduction: SAINT (Bruker, 2016); program(s) used to solve structure: ShelXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL (Sheldrick, 2015b); molecular graphics: OLEX2 (Dolomanov et al., 2009); VESTA (Momma & Izumi, 2011); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

(1R,3S,4R)-1,7,7-Trimethyl-3-(naphthalen-2-ylcarbonyl)bicyclo[2.2.1]heptan-2-one top

Crystal data top

C₂₁H₂₂O₂	Melting point: 399 K
M_r = 306.38	Cu Kα radiation, λ = 1.54178 Å
Tetragonal, P4₁2₁2	Cell parameters from 9853 reflections
a = 9.5637 (3) Å	θ = 4.6–74.7°
c = 36.3395 (10) Å	µ = 0.60 mm⁻¹
V = 3323.8 (2) Å³	T = 173 K
Z = 8	Block, colourless
F(000) = 1312	0.41 × 0.33 × 0.17 mm
D_x = 1.225 Mg m⁻³

Data collection top

Bruker PHOTON-100 CMOS diffractometer	3363 independent reflections
Radiation source: sealedtube	3123 reflections with I > 2σ(I)
Detector resolution: 10.8 pixels mm^-1	R_int = 0.034
φ and ω scans	θ_max = 75.2°, θ_min = 4.8°
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	h = −11→9
T_min = 0.922, T_max = 1.000	k = −11→10
27362 measured reflections	l = −43→45

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.042	H-atom parameters constrained
wR(F²) = 0.110	w = 1/[σ²(F_o²) + (0.0568P)² + 0.9139P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max = 0.001
3363 reflections	Δρ_max = 0.33 e Å⁻³
211 parameters	Δρ_min = −0.16 e Å⁻³
0 restraints	Absolute structure: Flack x determined using 1176 quotients [(I⁺)-(I^-)]/[(I⁺)+(I^-)] (Parsons et al., 2013)
Primary atom site location: dual	Absolute structure parameter: −0.04 (10)

Special details top

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.

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

	x	y	z	U_iso*/U_eq
O1	0.70347 (19)	0.6575 (2)	0.64361 (5)	0.0464 (4)
O2	0.5159 (2)	0.51669 (19)	0.69923 (4)	0.0496 (5)
C1	0.6066 (2)	0.5955 (2)	0.62993 (5)	0.0332 (5)
C12	0.5164 (2)	0.2695 (3)	0.69118 (6)	0.0365 (5)
C20	0.4639 (2)	0.1076 (3)	0.74128 (6)	0.0352 (5)
C2	0.5645 (2)	0.4436 (2)	0.63805 (6)	0.0322 (5)
H2	0.641392	0.379430	0.630123	0.039*
C11	0.5318 (2)	0.4187 (2)	0.67846 (6)	0.0361 (5)
C4	0.4804 (2)	0.5150 (2)	0.57811 (6)	0.0353 (5)
C21	0.4779 (2)	0.2461 (3)	0.72708 (6)	0.0377 (5)
H21	0.460193	0.323627	0.742761	0.045*
C5	0.5053 (2)	0.6502 (2)	0.60124 (6)	0.0367 (5)
C3	0.4366 (2)	0.4255 (2)	0.61188 (6)	0.0332 (5)
H3	0.413105	0.326134	0.605939	0.040*
C7	0.3144 (2)	0.5104 (3)	0.62806 (6)	0.0409 (5)
H7A	0.299828	0.488296	0.654394	0.049*
H7B	0.226558	0.492847	0.614409	0.049*
C15	0.4932 (2)	−0.0064 (3)	0.71753 (6)	0.0394 (5)
C13	0.5416 (2)	0.1533 (3)	0.66742 (6)	0.0387 (5)
H13	0.565984	0.168661	0.642397	0.046*
C14	0.5307 (2)	0.0201 (3)	0.68070 (7)	0.0408 (5)
H14	0.548878	−0.056467	0.664725	0.049*
C8	0.3638 (3)	0.5307 (3)	0.54932 (7)	0.0499 (6)
H8A	0.282051	0.574768	0.560714	0.075*
H8B	0.337812	0.438197	0.539925	0.075*
H8C	0.397117	0.589021	0.528961	0.075*
C9	0.6120 (3)	0.4631 (3)	0.55838 (6)	0.0426 (6)
H9A	0.640885	0.532133	0.539957	0.064*
H9B	0.591951	0.373884	0.546203	0.064*
H9C	0.687276	0.450052	0.576340	0.064*
C19	0.4206 (3)	0.0829 (3)	0.77769 (7)	0.0438 (6)
H19	0.400420	0.159300	0.793543	0.053*
C16	0.4805 (3)	−0.1453 (3)	0.73169 (8)	0.0496 (6)
H16	0.501686	−0.223071	0.716425	0.060*
C6	0.3646 (3)	0.6628 (3)	0.62289 (7)	0.0442 (6)
H6A	0.379542	0.708616	0.647000	0.053*
H6B	0.295274	0.717616	0.608703	0.053*
C10	0.5525 (3)	0.7813 (3)	0.58164 (7)	0.0523 (7)
H10A	0.565896	0.856496	0.599628	0.078*
H10B	0.481338	0.809412	0.563703	0.078*
H10C	0.640935	0.763122	0.568879	0.078*
C17	0.4383 (3)	−0.1660 (3)	0.76687 (8)	0.0537 (7)
H17	0.429241	−0.258625	0.776009	0.064*
C18	0.4076 (3)	−0.0513 (3)	0.79021 (7)	0.0513 (7)
H18	0.377741	−0.067775	0.814759	0.062*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0456 (10)	0.0561 (11)	0.0375 (8)	−0.0160 (8)	−0.0059 (7)	0.0023 (8)
O2	0.0678 (12)	0.0467 (10)	0.0343 (8)	0.0024 (8)	0.0081 (8)	0.0006 (7)
C1	0.0344 (11)	0.0380 (12)	0.0273 (9)	−0.0036 (9)	0.0034 (8)	0.0012 (8)
C12	0.0288 (11)	0.0459 (13)	0.0350 (10)	0.0010 (9)	−0.0009 (9)	0.0071 (9)
C20	0.0255 (10)	0.0455 (13)	0.0345 (10)	−0.0012 (9)	−0.0056 (8)	0.0008 (9)
C2	0.0295 (10)	0.0364 (11)	0.0308 (10)	0.0007 (9)	0.0018 (8)	0.0020 (8)
C11	0.0370 (12)	0.0401 (12)	0.0311 (10)	0.0025 (9)	0.0002 (9)	0.0040 (9)
C4	0.0310 (11)	0.0442 (13)	0.0306 (10)	−0.0031 (9)	−0.0019 (8)	0.0020 (9)
C21	0.0352 (11)	0.0427 (13)	0.0353 (10)	0.0021 (10)	−0.0015 (9)	0.0014 (10)
C5	0.0369 (12)	0.0385 (12)	0.0347 (10)	0.0005 (10)	−0.0007 (9)	0.0052 (9)
C3	0.0290 (11)	0.0370 (11)	0.0337 (10)	−0.0032 (9)	0.0015 (8)	−0.0005 (9)
C7	0.0301 (11)	0.0519 (15)	0.0406 (11)	0.0001 (10)	0.0035 (9)	0.0008 (10)
C15	0.0283 (11)	0.0460 (13)	0.0439 (11)	0.0014 (9)	−0.0072 (9)	0.0020 (10)
C13	0.0353 (12)	0.0439 (13)	0.0370 (11)	0.0023 (10)	0.0012 (9)	0.0007 (10)
C14	0.0351 (12)	0.0441 (13)	0.0432 (11)	0.0052 (10)	−0.0010 (10)	−0.0066 (10)
C8	0.0410 (14)	0.0705 (18)	0.0381 (12)	−0.0032 (13)	−0.0088 (10)	0.0036 (12)
C9	0.0380 (12)	0.0572 (15)	0.0324 (10)	−0.0050 (11)	0.0045 (9)	−0.0035 (10)
C19	0.0396 (13)	0.0527 (15)	0.0390 (11)	−0.0023 (11)	−0.0045 (10)	0.0055 (11)
C16	0.0442 (14)	0.0422 (14)	0.0625 (16)	−0.0025 (11)	−0.0117 (12)	0.0047 (12)
C6	0.0416 (13)	0.0442 (13)	0.0467 (13)	0.0101 (11)	0.0013 (11)	0.0008 (11)
C10	0.0639 (18)	0.0459 (15)	0.0471 (13)	−0.0080 (13)	−0.0071 (12)	0.0129 (11)
C17	0.0502 (16)	0.0447 (14)	0.0662 (16)	−0.0085 (12)	−0.0135 (13)	0.0198 (13)
C18	0.0438 (14)	0.0618 (17)	0.0482 (13)	−0.0051 (12)	−0.0043 (11)	0.0181 (12)

Geometric parameters (Å, º) top

O1—C1	1.207 (3)	C7—C6	1.545 (4)
O2—C11	1.213 (3)	C15—C14	1.409 (3)
C1—C2	1.535 (3)	C15—C16	1.430 (4)
C1—C5	1.516 (3)	C13—H13	0.9500
C12—C11	1.507 (3)	C13—C14	1.367 (4)
C12—C21	1.374 (3)	C14—H14	0.9500
C12—C13	1.428 (3)	C8—H8A	0.9800
C20—C21	1.428 (3)	C8—H8B	0.9800
C20—C15	1.418 (3)	C8—H8C	0.9800
C20—C19	1.406 (3)	C9—H9A	0.9800
C2—H2	1.0000	C9—H9B	0.9800
C2—C11	1.521 (3)	C9—H9C	0.9800
C2—C3	1.559 (3)	C19—H19	0.9500
C4—C5	1.560 (3)	C19—C18	1.367 (4)
C4—C3	1.554 (3)	C16—H16	0.9500
C4—C8	1.537 (3)	C16—C17	1.355 (4)
C4—C9	1.531 (3)	C6—H6A	0.9900
C21—H21	0.9500	C6—H6B	0.9900
C5—C6	1.564 (3)	C10—H10A	0.9800
C5—C10	1.511 (3)	C10—H10B	0.9800
C3—H3	1.0000	C10—H10C	0.9800
C3—C7	1.540 (3)	C17—H17	0.9500
C7—H7A	0.9900	C17—C18	1.418 (4)
C7—H7B	0.9900	C18—H18	0.9500

O1—C1—C2	125.9 (2)	C20—C15—C16	118.6 (2)
O1—C1—C5	127.1 (2)	C14—C15—C20	119.4 (2)
C5—C1—C2	106.96 (18)	C14—C15—C16	122.0 (2)
C21—C12—C11	118.1 (2)	C12—C13—H13	120.0
C21—C12—C13	119.5 (2)	C14—C13—C12	120.0 (2)
C13—C12—C11	122.31 (19)	C14—C13—H13	120.0
C15—C20—C21	118.3 (2)	C15—C14—H14	119.3
C19—C20—C21	121.5 (2)	C13—C14—C15	121.5 (2)
C19—C20—C15	120.1 (2)	C13—C14—H14	119.3
C1—C2—H2	109.5	C4—C8—H8A	109.5
C1—C2—C3	101.15 (16)	C4—C8—H8B	109.5
C11—C2—C1	112.83 (18)	C4—C8—H8C	109.5
C11—C2—H2	109.5	H8A—C8—H8B	109.5
C11—C2—C3	114.20 (17)	H8A—C8—H8C	109.5
C3—C2—H2	109.5	H8B—C8—H8C	109.5
O2—C11—C12	121.90 (19)	C4—C9—H9A	109.5
O2—C11—C2	120.4 (2)	C4—C9—H9B	109.5
C12—C11—C2	117.72 (19)	C4—C9—H9C	109.5
C3—C4—C5	94.14 (16)	H9A—C9—H9B	109.5
C8—C4—C5	113.4 (2)	H9A—C9—H9C	109.5
C8—C4—C3	113.29 (19)	H9B—C9—H9C	109.5
C9—C4—C5	113.31 (19)	C20—C19—H19	120.1
C9—C4—C3	114.39 (19)	C18—C19—C20	119.8 (3)
C9—C4—C8	108.02 (19)	C18—C19—H19	120.1
C12—C21—C20	121.3 (2)	C15—C16—H16	120.0
C12—C21—H21	119.4	C17—C16—C15	120.1 (3)
C20—C21—H21	119.4	C17—C16—H16	120.0
C1—C5—C4	100.46 (18)	C5—C6—H6A	110.8
C1—C5—C6	103.31 (18)	C5—C6—H6B	110.8
C4—C5—C6	101.74 (18)	C7—C6—C5	104.83 (19)
C10—C5—C1	114.8 (2)	C7—C6—H6A	110.8
C10—C5—C4	118.64 (19)	C7—C6—H6B	110.8
C10—C5—C6	115.5 (2)	H6A—C6—H6B	108.9
C2—C3—H3	114.4	C5—C10—H10A	109.5
C4—C3—C2	102.03 (16)	C5—C10—H10B	109.5
C4—C3—H3	114.4	C5—C10—H10C	109.5
C7—C3—C2	107.70 (17)	H10A—C10—H10B	109.5
C7—C3—C4	102.45 (18)	H10A—C10—H10C	109.5
C7—C3—H3	114.4	H10B—C10—H10C	109.5
C3—C7—H7A	111.3	C16—C17—H17	119.6
C3—C7—H7B	111.3	C16—C17—C18	120.8 (3)
C3—C7—C6	102.44 (18)	C18—C17—H17	119.6
H7A—C7—H7B	109.2	C19—C18—C17	120.6 (2)
C6—C7—H7A	111.3	C19—C18—H18	119.7
C6—C7—H7B	111.3	C17—C18—H18	119.7

O1—C1—C2—C11	58.5 (3)	C5—C4—C3—C2	−55.30 (19)
O1—C1—C2—C3	−179.1 (2)	C5—C4—C3—C7	56.14 (19)
O1—C1—C5—C4	144.2 (2)	C3—C2—C11—O2	−101.7 (3)
O1—C1—C5—C6	−110.9 (3)	C3—C2—C11—C12	76.7 (3)
O1—C1—C5—C10	15.7 (3)	C3—C4—C5—C1	54.17 (19)
C1—C2—C11—O2	13.1 (3)	C3—C4—C5—C6	−51.94 (19)
C1—C2—C11—C12	−168.51 (19)	C3—C4—C5—C10	−179.9 (2)
C1—C2—C3—C4	35.2 (2)	C3—C7—C6—C5	4.6 (2)
C1—C2—C3—C7	−72.2 (2)	C15—C20—C21—C12	1.1 (3)
C1—C5—C6—C7	−73.3 (2)	C15—C20—C19—C18	0.4 (3)
C12—C13—C14—C15	0.8 (4)	C15—C16—C17—C18	−0.6 (4)
C20—C15—C14—C13	1.0 (3)	C13—C12—C11—O2	−176.8 (2)
C20—C15—C16—C17	1.4 (4)	C13—C12—C11—C2	4.8 (3)
C20—C19—C18—C17	0.4 (4)	C13—C12—C21—C20	0.6 (3)
C2—C1—C5—C4	−34.7 (2)	C14—C15—C16—C17	−177.2 (2)
C2—C1—C5—C6	70.1 (2)	C8—C4—C5—C1	171.77 (19)
C2—C1—C5—C10	−163.2 (2)	C8—C4—C5—C6	65.7 (2)
C2—C3—C7—C6	68.6 (2)	C8—C4—C5—C10	−62.3 (3)
C11—C12—C21—C20	−178.8 (2)	C8—C4—C3—C2	−172.96 (19)
C11—C12—C13—C14	177.8 (2)	C8—C4—C3—C7	−61.5 (2)
C11—C2—C3—C4	156.71 (18)	C9—C4—C5—C1	−64.6 (2)
C11—C2—C3—C7	49.3 (2)	C9—C4—C5—C6	−170.76 (18)
C4—C5—C6—C7	30.5 (2)	C9—C4—C5—C10	61.3 (3)
C4—C3—C7—C6	−38.6 (2)	C9—C4—C3—C2	62.6 (2)
C21—C12—C11—O2	2.6 (3)	C9—C4—C3—C7	174.07 (19)
C21—C12—C11—C2	−175.8 (2)	C19—C20—C21—C12	−178.1 (2)
C21—C12—C13—C14	−1.6 (3)	C19—C20—C15—C14	177.3 (2)
C21—C20—C15—C14	−1.9 (3)	C19—C20—C15—C16	−1.3 (3)
C21—C20—C15—C16	179.5 (2)	C16—C15—C14—C13	179.6 (2)
C21—C20—C19—C18	179.6 (2)	C16—C17—C18—C19	−0.3 (4)
C5—C1—C2—C11	−122.51 (19)	C10—C5—C6—C7	160.4 (2)
C5—C1—C2—C3	−0.1 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13···O1ⁱ	0.95	2.57	3.296 (3)	134
C16—H16···O2ⁱⁱ	0.95	2.57	3.458 (3)	156

Symmetry codes: (i) −x+3/2, y−1/2, −z+5/4; (ii) x, y−1, z.

Acknowledgements

Help from the CLAC Laboratory at Chemistry Institute of the University of Strasbourg is gratefully acknowledged.

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