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The crystal structure of the title compound, C23H22O2, which exists in the enol form, is stabilized by an intra­molecular hydrogen bond. The dihedral angle between the naphthyl ring system and the aromatic ring of the t-BuC6H4 group is 23.50 (10)°.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806029084/tk2062sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806029084/tk2062Isup2.hkl
Contains datablock I

CCDC reference: 621509

Key indicators

  • Single-crystal X-ray study
  • T = 292 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.061
  • wR factor = 0.164
  • Data-to-parameter ratio = 17.3

checkCIF/PLATON results

No syntax errors found



Alert level A PLAT772_ALERT_2_A Suspect O-H Bond in CIF: O1 -H1 .. 1.36 Ang.
Author Response: The bond is an intramolecular hydrogen bond, the enolic proton position is not in the middle of the O1--O2 because of tautomeric equilibrium ---O1---H--O2 \\db and \\db O1--H---O2---, the O--H Bond length is in agreement with reported literature values (Bertolasi et al., 1991; Gilli et al., 2004).

Alert level C RINTA01_ALERT_3_C The value of Rint is greater than 0.10 Rint given 0.101 PLAT020_ALERT_3_C The value of Rint is greater than 0.10 ......... 0.10 PLAT230_ALERT_2_C Hirshfeld Test Diff for C1 - C4 .. 5.03 su PLAT230_ALERT_2_C Hirshfeld Test Diff for C8 - C11 .. 5.08 su PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C4
1 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 5 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 4 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SMART; data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2001); software used to prepare material for publication: SHELXTL.

1-(4-tert-Butylphenyl)-3-hydroxy-3-(2-naphthyl)prop-2-en-1-one top
Crystal data top
C23H22O2F(000) = 1408
Mr = 330.41Dx = 1.233 Mg m3
Monoclinic, C2/cMelting point: 340 K
Hall symbol: -C2ycMo Kα radiation, λ = 0.71073 Å
a = 32.490 (4) ÅCell parameters from 3719 reflections
b = 6.2231 (8) Åθ = 2.3–27.5°
c = 22.533 (3) ŵ = 0.08 mm1
β = 128.605 (2)°T = 292 K
V = 3560.2 (8) Å3Block, colorless
Z = 80.30 × 0.20 × 0.20 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer
4055 independent reflections
Radiation source: fine-focus sealed tube2810 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.101
Detector resolution: 0 pixels mm-1θmax = 27.5°, θmin = 1.6°
φ and ω scansh = 4242
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
k = 88
Tmin = 0.977, Tmax = 0.982l = 2929
15619 measured reflections
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)] = 0.061Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.164H atoms treated by a mixture of independent and constrained refinement
S = 1.02 w = 1/[σ2(Fo2) + (0.0858P)2]
where P = (Fo2 + 2Fc2)/3
4055 reflections(Δ/σ)max < 0.001
234 parametersΔρmax = 0.22 e Å3
0 restraintsΔρmin = 0.25 e Å3
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
C10.52312 (7)0.4576 (3)1.10587 (10)0.0696 (5)
H1A0.50440.35951.06380.104*
H1B0.54660.37871.15230.104*
H1C0.54300.55591.09980.104*
C20.51384 (10)0.7495 (3)1.17197 (11)0.0873 (6)
H2A0.53370.84011.16370.131*
H2B0.53740.67741.21990.131*
H2C0.48940.83541.17230.131*
C30.45729 (8)0.4263 (4)1.12740 (11)0.0822 (6)
H3A0.43140.50081.12730.123*
H3B0.48330.36491.17660.123*
H3C0.44050.31401.09000.123*
C40.48372 (6)0.5837 (2)1.10864 (8)0.0491 (4)
C50.44385 (5)0.6886 (2)1.03080 (8)0.0439 (4)
C60.45241 (6)0.8920 (3)1.01503 (9)0.0568 (4)
H60.48220.96801.05350.068*
C70.41851 (7)0.9846 (3)0.94476 (10)0.0564 (4)
H70.42561.12180.93680.068*
C80.37382 (6)0.8770 (2)0.88524 (8)0.0446 (4)
C90.36475 (6)0.6735 (2)0.90011 (9)0.0498 (4)
H90.33520.59700.86130.060*
C100.39852 (6)0.5827 (2)0.97099 (9)0.0501 (4)
H100.39090.44710.97930.060*
C110.33878 (6)0.9834 (2)0.81039 (9)0.0511 (4)
C120.29937 (6)0.8765 (2)0.74332 (8)0.0499 (4)
H120.29150.73420.74530.060*
C130.27165 (6)0.9808 (2)0.67346 (9)0.0495 (4)
C140.23474 (6)0.8707 (2)0.59985 (8)0.0464 (4)
C150.22066 (6)0.9705 (2)0.53512 (9)0.0471 (4)
H150.23341.10780.53880.057*
C160.18753 (5)0.8710 (2)0.46341 (9)0.0457 (4)
C170.17393 (6)0.9710 (3)0.39697 (9)0.0552 (4)
H170.18701.10710.40000.066*
C180.14204 (7)0.8701 (3)0.32876 (10)0.0646 (5)
H180.13340.93740.28540.078*
C190.12221 (7)0.6662 (3)0.32332 (11)0.0688 (5)
H190.10040.59900.27620.083*
C200.13420 (7)0.5642 (3)0.38552 (10)0.0632 (5)
H200.12050.42820.38070.076*
C210.16757 (6)0.6639 (2)0.45815 (9)0.0498 (4)
C220.18168 (6)0.5647 (2)0.52489 (10)0.0570 (4)
H220.16840.42930.52190.068*
C230.21432 (6)0.6635 (3)0.59342 (9)0.0536 (4)
H230.22340.59410.63670.064*
O10.34739 (6)1.18445 (18)0.80858 (7)0.0758 (4)
H10.3119 (10)1.224 (4)0.7329 (14)0.137 (9)*
O20.27924 (5)1.18291 (17)0.67066 (7)0.0710 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0607 (11)0.0834 (13)0.0642 (11)0.0150 (9)0.0388 (10)0.0122 (10)
C20.1013 (16)0.0788 (13)0.0525 (11)0.0049 (12)0.0337 (11)0.0125 (10)
C30.0675 (12)0.1152 (17)0.0641 (12)0.0081 (11)0.0413 (11)0.0215 (11)
C40.0448 (8)0.0566 (9)0.0456 (9)0.0051 (7)0.0280 (7)0.0033 (7)
C50.0426 (8)0.0483 (8)0.0471 (8)0.0019 (6)0.0310 (7)0.0046 (7)
C60.0495 (9)0.0570 (10)0.0542 (10)0.0157 (7)0.0275 (8)0.0079 (8)
C70.0589 (10)0.0458 (9)0.0615 (11)0.0099 (7)0.0361 (9)0.0018 (8)
C80.0468 (8)0.0458 (8)0.0480 (8)0.0010 (6)0.0330 (7)0.0028 (6)
C90.0455 (8)0.0511 (9)0.0462 (9)0.0088 (7)0.0255 (7)0.0064 (7)
C100.0517 (9)0.0450 (8)0.0517 (9)0.0067 (7)0.0313 (8)0.0010 (7)
C110.0578 (10)0.0460 (9)0.0586 (10)0.0003 (7)0.0408 (9)0.0002 (7)
C120.0545 (9)0.0454 (8)0.0532 (9)0.0013 (7)0.0352 (8)0.0033 (7)
C130.0518 (9)0.0477 (9)0.0560 (10)0.0031 (7)0.0370 (8)0.0043 (7)
C140.0411 (8)0.0470 (8)0.0530 (9)0.0067 (6)0.0303 (7)0.0078 (7)
C150.0423 (8)0.0420 (8)0.0571 (10)0.0019 (6)0.0310 (8)0.0051 (7)
C160.0360 (7)0.0480 (8)0.0532 (9)0.0057 (6)0.0279 (7)0.0032 (7)
C170.0453 (9)0.0606 (10)0.0578 (10)0.0044 (7)0.0314 (8)0.0075 (8)
C180.0532 (10)0.0832 (13)0.0536 (10)0.0059 (9)0.0314 (9)0.0008 (9)
C190.0532 (10)0.0859 (14)0.0579 (11)0.0020 (9)0.0301 (9)0.0151 (10)
C200.0500 (10)0.0579 (10)0.0740 (13)0.0045 (8)0.0349 (9)0.0119 (9)
C210.0377 (8)0.0497 (9)0.0605 (10)0.0048 (7)0.0299 (8)0.0011 (7)
C220.0506 (9)0.0456 (9)0.0748 (12)0.0021 (7)0.0391 (9)0.0045 (8)
C230.0499 (9)0.0528 (9)0.0586 (10)0.0022 (7)0.0340 (8)0.0111 (8)
O10.0957 (10)0.0456 (7)0.0617 (8)0.0087 (6)0.0371 (8)0.0001 (6)
O20.0883 (9)0.0449 (7)0.0597 (8)0.0020 (6)0.0364 (7)0.0058 (6)
Geometric parameters (Å, º) top
C1—C41.536 (2)O2—C131.2908 (18)
C1—H1A0.9600C11—C121.397 (2)
C1—H1B0.9600C12—C131.393 (2)
C1—H1C0.9600C12—H120.9300
C2—C41.522 (2)C13—C141.475 (2)
C2—H2A0.9600C14—C151.375 (2)
C2—H2B0.9600C14—C231.416 (2)
C2—H2C0.9600C15—C161.408 (2)
C3—C41.526 (2)C15—H150.9300
C3—H3A0.9600C16—C171.414 (2)
C3—H3B0.9600C16—C211.414 (2)
C3—H3C0.9600C17—C181.357 (2)
C4—C51.531 (2)C17—H170.9300
C5—C61.389 (2)C18—C191.393 (3)
C5—C101.394 (2)C18—H180.9300
C6—C71.370 (2)C19—C201.356 (3)
C6—H60.9300C19—H190.9300
C7—C81.388 (2)C20—C211.423 (2)
C7—H70.9300C20—H200.9300
C8—C91.388 (2)C21—C221.411 (2)
C8—C111.478 (2)C22—C231.358 (2)
C9—C101.374 (2)C22—H220.9300
C9—H90.9300C23—H230.9300
C10—H100.9300O1—H11.36 (3)
O1—C111.2881 (19)O2—H11.14 (3)
C4—C1—H1A109.5O1—C11—C12119.92 (14)
C4—C1—H1B109.5O1—C11—C8116.34 (14)
H1A—C1—H1B109.5C12—C11—C8123.69 (14)
C4—C1—H1C109.5C11—C12—C13120.70 (14)
H1A—C1—H1C109.5C13—C12—H12119.7
H1B—C1—H1C109.5C11—C12—H12119.7
C4—C2—H2A109.5O2—C13—C12120.04 (15)
C4—C2—H2B109.5O2—C13—C14116.33 (14)
H2A—C2—H2B109.5C12—C13—C14123.58 (14)
C4—C2—H2C109.5C15—C14—C23118.59 (15)
H2A—C2—H2C109.5C15—C14—C13118.82 (14)
H2B—C2—H2C109.5C23—C14—C13122.57 (14)
C4—C3—H3A109.5C14—C15—C16121.94 (14)
C4—C3—H3B109.5C14—C15—H15119.0
H3A—C3—H3B109.5C16—C15—H15119.0
C4—C3—H3C109.5C15—C16—C17122.13 (14)
H3A—C3—H3C109.5C15—C16—C21118.64 (14)
H3B—C3—H3C109.5C17—C16—C21119.23 (15)
C2—C4—C3108.61 (15)C18—C17—C16120.59 (16)
C2—C4—C5112.02 (14)C18—C17—H17119.7
C3—C4—C5111.76 (13)C16—C17—H17119.7
C2—C4—C1108.65 (15)C17—C18—C19120.35 (17)
C3—C4—C1108.09 (15)C17—C18—H18119.8
C5—C4—C1107.59 (12)C19—C18—H18119.8
C6—C5—C10116.30 (14)C20—C19—C18121.11 (17)
C6—C5—C4121.33 (13)C20—C19—H19119.4
C10—C5—C4122.29 (13)C18—C19—H19119.4
C7—C6—C5122.30 (15)C19—C20—C21120.40 (16)
C7—C6—H6118.9C19—C20—H20119.8
C5—C6—H6118.9C21—C20—H20119.8
C6—C7—C8121.05 (14)C22—C21—C16118.81 (15)
C6—C7—H7119.5C22—C21—C20122.88 (15)
C8—C7—H7119.5C16—C21—C20118.31 (15)
C7—C8—C9117.32 (14)C23—C22—C21121.19 (14)
C7—C8—C11118.89 (14)C23—C22—H22119.4
C9—C8—C11123.79 (14)C21—C22—H22119.4
C10—C9—C8121.35 (14)C22—C23—C14120.82 (15)
C10—C9—H9119.3C22—C23—H23119.6
C8—C9—H9119.3C14—C23—H23119.6
C9—C10—C5121.67 (14)C11—O1—H1100.7 (12)
C9—C10—H10119.2C13—O2—H1102.6 (14)
C5—C10—H10119.2
C2—C4—C5—C629.8 (2)O2—C13—C14—C1515.0 (2)
C3—C4—C5—C6151.98 (16)C12—C13—C14—C15162.25 (14)
C1—C4—C5—C689.52 (18)O2—C13—C14—C23166.84 (14)
C2—C4—C5—C10153.33 (16)C12—C13—C14—C2315.9 (2)
C3—C4—C5—C1031.2 (2)C23—C14—C15—C161.2 (2)
C1—C4—C5—C1087.32 (17)C13—C14—C15—C16177.07 (12)
C10—C5—C6—C70.2 (2)C14—C15—C16—C17178.51 (13)
C4—C5—C6—C7176.85 (14)C14—C15—C16—C211.1 (2)
C5—C6—C7—C80.7 (3)C15—C16—C17—C18179.75 (14)
C6—C7—C8—C90.6 (2)C21—C16—C17—C180.1 (2)
C6—C7—C8—C11179.50 (14)C16—C17—C18—C190.0 (2)
C7—C8—C9—C100.3 (2)C17—C18—C19—C200.0 (3)
C11—C8—C9—C10179.60 (14)C18—C19—C20—C210.1 (3)
C8—C9—C10—C51.2 (2)C15—C16—C21—C220.1 (2)
C6—C5—C10—C91.1 (2)C17—C16—C21—C22179.54 (14)
C4—C5—C10—C9175.91 (13)C15—C16—C21—C20179.86 (13)
C7—C8—C11—O111.3 (2)C17—C16—C21—C200.2 (2)
C9—C8—C11—O1168.62 (15)C19—C20—C21—C22179.54 (16)
C7—C8—C11—C12166.22 (14)C19—C20—C21—C160.2 (2)
C9—C8—C11—C1213.9 (2)C16—C21—C22—C230.8 (2)
O1—C11—C12—C134.6 (2)C20—C21—C22—C23178.90 (14)
C8—C11—C12—C13172.79 (13)C21—C22—C23—C140.8 (2)
C11—C12—C13—O25.6 (2)C15—C14—C23—C220.2 (2)
C11—C12—C13—C14171.52 (13)C13—C14—C23—C22177.98 (14)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H1···O11.14 (3)1.36 (3)2.4441 (17)156 (2)
 

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