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
CCDC reference: 621509
Key indicators
- Single-crystal X-ray study
- T = 292 K
- Mean (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
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
C23H22O2 | F(000) = 1408 |
Mr = 330.41 | Dx = 1.233 Mg m−3 |
Monoclinic, C2/c | Melting point: 340 K |
Hall symbol: -C2yc | Mo Kα radiation, λ = 0.71073 Å |
a = 32.490 (4) Å | Cell parameters from 3719 reflections |
b = 6.2231 (8) Å | θ = 2.3–27.5° |
c = 22.533 (3) Å | µ = 0.08 mm−1 |
β = 128.605 (2)° | T = 292 K |
V = 3560.2 (8) Å3 | Block, colorless |
Z = 8 | 0.30 × 0.20 × 0.20 mm |
Data collection top
Bruker SMART CCD area-detector diffractometer | 4055 independent reflections |
Radiation source: fine-focus sealed tube | 2810 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.101 |
Detector resolution: 0 pixels mm-1 | θmax = 27.5°, θmin = 1.6° |
φ and ω scans | h = −42→42 |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | k = −8→8 |
Tmin = 0.977, Tmax = 0.982 | l = −29→29 |
15619 measured reflections | |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.061 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.164 | H 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 parameters | Δρmax = 0.22 e Å−3 |
0 restraints | Δρmin = −0.25 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
C1 | 0.52312 (7) | 0.4576 (3) | 1.10587 (10) | 0.0696 (5) | |
H1A | 0.5044 | 0.3595 | 1.0638 | 0.104* | |
H1B | 0.5466 | 0.3787 | 1.1523 | 0.104* | |
H1C | 0.5430 | 0.5559 | 1.0998 | 0.104* | |
C2 | 0.51384 (10) | 0.7495 (3) | 1.17197 (11) | 0.0873 (6) | |
H2A | 0.5337 | 0.8401 | 1.1637 | 0.131* | |
H2B | 0.5374 | 0.6774 | 1.2199 | 0.131* | |
H2C | 0.4894 | 0.8354 | 1.1723 | 0.131* | |
C3 | 0.45729 (8) | 0.4263 (4) | 1.12740 (11) | 0.0822 (6) | |
H3A | 0.4314 | 0.5008 | 1.1273 | 0.123* | |
H3B | 0.4833 | 0.3649 | 1.1766 | 0.123* | |
H3C | 0.4405 | 0.3140 | 1.0900 | 0.123* | |
C4 | 0.48372 (6) | 0.5837 (2) | 1.10864 (8) | 0.0491 (4) | |
C5 | 0.44385 (5) | 0.6886 (2) | 1.03080 (8) | 0.0439 (4) | |
C6 | 0.45241 (6) | 0.8920 (3) | 1.01503 (9) | 0.0568 (4) | |
H6 | 0.4822 | 0.9680 | 1.0535 | 0.068* | |
C7 | 0.41851 (7) | 0.9846 (3) | 0.94476 (10) | 0.0564 (4) | |
H7 | 0.4256 | 1.1218 | 0.9368 | 0.068* | |
C8 | 0.37382 (6) | 0.8770 (2) | 0.88524 (8) | 0.0446 (4) | |
C9 | 0.36475 (6) | 0.6735 (2) | 0.90011 (9) | 0.0498 (4) | |
H9 | 0.3352 | 0.5970 | 0.8613 | 0.060* | |
C10 | 0.39852 (6) | 0.5827 (2) | 0.97099 (9) | 0.0501 (4) | |
H10 | 0.3909 | 0.4471 | 0.9793 | 0.060* | |
C11 | 0.33878 (6) | 0.9834 (2) | 0.81039 (9) | 0.0511 (4) | |
C12 | 0.29937 (6) | 0.8765 (2) | 0.74332 (8) | 0.0499 (4) | |
H12 | 0.2915 | 0.7342 | 0.7453 | 0.060* | |
C13 | 0.27165 (6) | 0.9808 (2) | 0.67346 (9) | 0.0495 (4) | |
C14 | 0.23474 (6) | 0.8707 (2) | 0.59985 (8) | 0.0464 (4) | |
C15 | 0.22066 (6) | 0.9705 (2) | 0.53512 (9) | 0.0471 (4) | |
H15 | 0.2334 | 1.1078 | 0.5388 | 0.057* | |
C16 | 0.18753 (5) | 0.8710 (2) | 0.46341 (9) | 0.0457 (4) | |
C17 | 0.17393 (6) | 0.9710 (3) | 0.39697 (9) | 0.0552 (4) | |
H17 | 0.1870 | 1.1071 | 0.4000 | 0.066* | |
C18 | 0.14204 (7) | 0.8701 (3) | 0.32876 (10) | 0.0646 (5) | |
H18 | 0.1334 | 0.9374 | 0.2854 | 0.078* | |
C19 | 0.12221 (7) | 0.6662 (3) | 0.32332 (11) | 0.0688 (5) | |
H19 | 0.1004 | 0.5990 | 0.2762 | 0.083* | |
C20 | 0.13420 (7) | 0.5642 (3) | 0.38552 (10) | 0.0632 (5) | |
H20 | 0.1205 | 0.4282 | 0.3807 | 0.076* | |
C21 | 0.16757 (6) | 0.6639 (2) | 0.45815 (9) | 0.0498 (4) | |
C22 | 0.18168 (6) | 0.5647 (2) | 0.52489 (10) | 0.0570 (4) | |
H22 | 0.1684 | 0.4293 | 0.5219 | 0.068* | |
C23 | 0.21432 (6) | 0.6635 (3) | 0.59342 (9) | 0.0536 (4) | |
H23 | 0.2234 | 0.5941 | 0.6367 | 0.064* | |
O1 | 0.34739 (6) | 1.18445 (18) | 0.80858 (7) | 0.0758 (4) | |
H1 | 0.3119 (10) | 1.224 (4) | 0.7329 (14) | 0.137 (9)* | |
O2 | 0.27924 (5) | 1.18291 (17) | 0.67066 (7) | 0.0710 (4) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0607 (11) | 0.0834 (13) | 0.0642 (11) | 0.0150 (9) | 0.0388 (10) | 0.0122 (10) |
C2 | 0.1013 (16) | 0.0788 (13) | 0.0525 (11) | −0.0049 (12) | 0.0337 (11) | −0.0125 (10) |
C3 | 0.0675 (12) | 0.1152 (17) | 0.0641 (12) | −0.0081 (11) | 0.0413 (11) | 0.0215 (11) |
C4 | 0.0448 (8) | 0.0566 (9) | 0.0456 (9) | −0.0051 (7) | 0.0280 (7) | −0.0033 (7) |
C5 | 0.0426 (8) | 0.0483 (8) | 0.0471 (8) | −0.0019 (6) | 0.0310 (7) | −0.0046 (7) |
C6 | 0.0495 (9) | 0.0570 (10) | 0.0542 (10) | −0.0157 (7) | 0.0275 (8) | −0.0079 (8) |
C7 | 0.0589 (10) | 0.0458 (9) | 0.0615 (11) | −0.0099 (7) | 0.0361 (9) | −0.0018 (8) |
C8 | 0.0468 (8) | 0.0458 (8) | 0.0480 (8) | −0.0010 (6) | 0.0330 (7) | −0.0028 (6) |
C9 | 0.0455 (8) | 0.0511 (9) | 0.0462 (9) | −0.0088 (7) | 0.0255 (7) | −0.0064 (7) |
C10 | 0.0517 (9) | 0.0450 (8) | 0.0517 (9) | −0.0067 (7) | 0.0313 (8) | −0.0010 (7) |
C11 | 0.0578 (10) | 0.0460 (9) | 0.0586 (10) | 0.0003 (7) | 0.0408 (9) | −0.0002 (7) |
C12 | 0.0545 (9) | 0.0454 (8) | 0.0532 (9) | −0.0013 (7) | 0.0352 (8) | 0.0033 (7) |
C13 | 0.0518 (9) | 0.0477 (9) | 0.0560 (10) | 0.0031 (7) | 0.0370 (8) | 0.0043 (7) |
C14 | 0.0411 (8) | 0.0470 (8) | 0.0530 (9) | 0.0067 (6) | 0.0303 (7) | 0.0078 (7) |
C15 | 0.0423 (8) | 0.0420 (8) | 0.0571 (10) | 0.0019 (6) | 0.0310 (8) | 0.0051 (7) |
C16 | 0.0360 (7) | 0.0480 (8) | 0.0532 (9) | 0.0057 (6) | 0.0279 (7) | 0.0032 (7) |
C17 | 0.0453 (9) | 0.0606 (10) | 0.0578 (10) | 0.0044 (7) | 0.0314 (8) | 0.0075 (8) |
C18 | 0.0532 (10) | 0.0832 (13) | 0.0536 (10) | 0.0059 (9) | 0.0314 (9) | 0.0008 (9) |
C19 | 0.0532 (10) | 0.0859 (14) | 0.0579 (11) | −0.0020 (9) | 0.0301 (9) | −0.0151 (10) |
C20 | 0.0500 (10) | 0.0579 (10) | 0.0740 (13) | −0.0045 (8) | 0.0349 (9) | −0.0119 (9) |
C21 | 0.0377 (8) | 0.0497 (9) | 0.0605 (10) | 0.0048 (7) | 0.0299 (8) | 0.0011 (7) |
C22 | 0.0506 (9) | 0.0456 (9) | 0.0748 (12) | −0.0021 (7) | 0.0391 (9) | 0.0045 (8) |
C23 | 0.0499 (9) | 0.0528 (9) | 0.0586 (10) | 0.0022 (7) | 0.0340 (8) | 0.0111 (8) |
O1 | 0.0957 (10) | 0.0456 (7) | 0.0617 (8) | −0.0087 (6) | 0.0371 (8) | −0.0001 (6) |
O2 | 0.0883 (9) | 0.0449 (7) | 0.0597 (8) | −0.0020 (6) | 0.0364 (7) | 0.0058 (6) |
Geometric parameters (Å, º) top
C1—C4 | 1.536 (2) | O2—C13 | 1.2908 (18) |
C1—H1A | 0.9600 | C11—C12 | 1.397 (2) |
C1—H1B | 0.9600 | C12—C13 | 1.393 (2) |
C1—H1C | 0.9600 | C12—H12 | 0.9300 |
C2—C4 | 1.522 (2) | C13—C14 | 1.475 (2) |
C2—H2A | 0.9600 | C14—C15 | 1.375 (2) |
C2—H2B | 0.9600 | C14—C23 | 1.416 (2) |
C2—H2C | 0.9600 | C15—C16 | 1.408 (2) |
C3—C4 | 1.526 (2) | C15—H15 | 0.9300 |
C3—H3A | 0.9600 | C16—C17 | 1.414 (2) |
C3—H3B | 0.9600 | C16—C21 | 1.414 (2) |
C3—H3C | 0.9600 | C17—C18 | 1.357 (2) |
C4—C5 | 1.531 (2) | C17—H17 | 0.9300 |
C5—C6 | 1.389 (2) | C18—C19 | 1.393 (3) |
C5—C10 | 1.394 (2) | C18—H18 | 0.9300 |
C6—C7 | 1.370 (2) | C19—C20 | 1.356 (3) |
C6—H6 | 0.9300 | C19—H19 | 0.9300 |
C7—C8 | 1.388 (2) | C20—C21 | 1.423 (2) |
C7—H7 | 0.9300 | C20—H20 | 0.9300 |
C8—C9 | 1.388 (2) | C21—C22 | 1.411 (2) |
C8—C11 | 1.478 (2) | C22—C23 | 1.358 (2) |
C9—C10 | 1.374 (2) | C22—H22 | 0.9300 |
C9—H9 | 0.9300 | C23—H23 | 0.9300 |
C10—H10 | 0.9300 | O1—H1 | 1.36 (3) |
O1—C11 | 1.2881 (19) | O2—H1 | 1.14 (3) |
| | | |
C4—C1—H1A | 109.5 | O1—C11—C12 | 119.92 (14) |
C4—C1—H1B | 109.5 | O1—C11—C8 | 116.34 (14) |
H1A—C1—H1B | 109.5 | C12—C11—C8 | 123.69 (14) |
C4—C1—H1C | 109.5 | C11—C12—C13 | 120.70 (14) |
H1A—C1—H1C | 109.5 | C13—C12—H12 | 119.7 |
H1B—C1—H1C | 109.5 | C11—C12—H12 | 119.7 |
C4—C2—H2A | 109.5 | O2—C13—C12 | 120.04 (15) |
C4—C2—H2B | 109.5 | O2—C13—C14 | 116.33 (14) |
H2A—C2—H2B | 109.5 | C12—C13—C14 | 123.58 (14) |
C4—C2—H2C | 109.5 | C15—C14—C23 | 118.59 (15) |
H2A—C2—H2C | 109.5 | C15—C14—C13 | 118.82 (14) |
H2B—C2—H2C | 109.5 | C23—C14—C13 | 122.57 (14) |
C4—C3—H3A | 109.5 | C14—C15—C16 | 121.94 (14) |
C4—C3—H3B | 109.5 | C14—C15—H15 | 119.0 |
H3A—C3—H3B | 109.5 | C16—C15—H15 | 119.0 |
C4—C3—H3C | 109.5 | C15—C16—C17 | 122.13 (14) |
H3A—C3—H3C | 109.5 | C15—C16—C21 | 118.64 (14) |
H3B—C3—H3C | 109.5 | C17—C16—C21 | 119.23 (15) |
C2—C4—C3 | 108.61 (15) | C18—C17—C16 | 120.59 (16) |
C2—C4—C5 | 112.02 (14) | C18—C17—H17 | 119.7 |
C3—C4—C5 | 111.76 (13) | C16—C17—H17 | 119.7 |
C2—C4—C1 | 108.65 (15) | C17—C18—C19 | 120.35 (17) |
C3—C4—C1 | 108.09 (15) | C17—C18—H18 | 119.8 |
C5—C4—C1 | 107.59 (12) | C19—C18—H18 | 119.8 |
C6—C5—C10 | 116.30 (14) | C20—C19—C18 | 121.11 (17) |
C6—C5—C4 | 121.33 (13) | C20—C19—H19 | 119.4 |
C10—C5—C4 | 122.29 (13) | C18—C19—H19 | 119.4 |
C7—C6—C5 | 122.30 (15) | C19—C20—C21 | 120.40 (16) |
C7—C6—H6 | 118.9 | C19—C20—H20 | 119.8 |
C5—C6—H6 | 118.9 | C21—C20—H20 | 119.8 |
C6—C7—C8 | 121.05 (14) | C22—C21—C16 | 118.81 (15) |
C6—C7—H7 | 119.5 | C22—C21—C20 | 122.88 (15) |
C8—C7—H7 | 119.5 | C16—C21—C20 | 118.31 (15) |
C7—C8—C9 | 117.32 (14) | C23—C22—C21 | 121.19 (14) |
C7—C8—C11 | 118.89 (14) | C23—C22—H22 | 119.4 |
C9—C8—C11 | 123.79 (14) | C21—C22—H22 | 119.4 |
C10—C9—C8 | 121.35 (14) | C22—C23—C14 | 120.82 (15) |
C10—C9—H9 | 119.3 | C22—C23—H23 | 119.6 |
C8—C9—H9 | 119.3 | C14—C23—H23 | 119.6 |
C9—C10—C5 | 121.67 (14) | C11—O1—H1 | 100.7 (12) |
C9—C10—H10 | 119.2 | C13—O2—H1 | 102.6 (14) |
C5—C10—H10 | 119.2 | | |
| | | |
C2—C4—C5—C6 | 29.8 (2) | O2—C13—C14—C15 | 15.0 (2) |
C3—C4—C5—C6 | 151.98 (16) | C12—C13—C14—C15 | −162.25 (14) |
C1—C4—C5—C6 | −89.52 (18) | O2—C13—C14—C23 | −166.84 (14) |
C2—C4—C5—C10 | −153.33 (16) | C12—C13—C14—C23 | 15.9 (2) |
C3—C4—C5—C10 | −31.2 (2) | C23—C14—C15—C16 | −1.2 (2) |
C1—C4—C5—C10 | 87.32 (17) | C13—C14—C15—C16 | 177.07 (12) |
C10—C5—C6—C7 | −0.2 (2) | C14—C15—C16—C17 | −178.51 (13) |
C4—C5—C6—C7 | 176.85 (14) | C14—C15—C16—C21 | 1.1 (2) |
C5—C6—C7—C8 | −0.7 (3) | C15—C16—C17—C18 | 179.75 (14) |
C6—C7—C8—C9 | 0.6 (2) | C21—C16—C17—C18 | 0.1 (2) |
C6—C7—C8—C11 | −179.50 (14) | C16—C17—C18—C19 | 0.0 (2) |
C7—C8—C9—C10 | 0.3 (2) | C17—C18—C19—C20 | 0.0 (3) |
C11—C8—C9—C10 | −179.60 (14) | C18—C19—C20—C21 | −0.1 (3) |
C8—C9—C10—C5 | −1.2 (2) | C15—C16—C21—C22 | −0.1 (2) |
C6—C5—C10—C9 | 1.1 (2) | C17—C16—C21—C22 | 179.54 (14) |
C4—C5—C10—C9 | −175.91 (13) | C15—C16—C21—C20 | −179.86 (13) |
C7—C8—C11—O1 | −11.3 (2) | C17—C16—C21—C20 | −0.2 (2) |
C9—C8—C11—O1 | 168.62 (15) | C19—C20—C21—C22 | −179.54 (16) |
C7—C8—C11—C12 | 166.22 (14) | C19—C20—C21—C16 | 0.2 (2) |
C9—C8—C11—C12 | −13.9 (2) | C16—C21—C22—C23 | −0.8 (2) |
O1—C11—C12—C13 | 4.6 (2) | C20—C21—C22—C23 | 178.90 (14) |
C8—C11—C12—C13 | −172.79 (13) | C21—C22—C23—C14 | 0.8 (2) |
C11—C12—C13—O2 | −5.6 (2) | C15—C14—C23—C22 | 0.2 (2) |
C11—C12—C13—C14 | 171.52 (13) | C13—C14—C23—C22 | −177.98 (14) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H1···O1 | 1.14 (3) | 1.36 (3) | 2.4441 (17) | 156 (2) |