The title molecule, C
18H
16O
3, exists in the enolized form and displays a strong intramolecular hydrogen bond. Except for van der Waals interactions, the intermolecular contacts are dominated by weak hydrogen bonding of the type C—H
O and aromatic C—H
π.
Supporting information
CCDC reference: 283909
Key indicators
- Single-crystal X-ray study
- T = 105 K
- Mean (C-C) = 0.002 Å
- R factor = 0.028
- wR factor = 0.079
- Data-to-parameter ratio = 13.6
checkCIF/PLATON results
No syntax errors found
Alert level A
PLAT222_ALERT_3_A Large Non-Solvent H Ueq(max)/Ueq(min) ... 5.50 Ratio
| Author Response: Such variation in the temperature factor for enol hydrogen atoms
is not uncommon as explained in the publ_section_comment.
|
PLAT772_ALERT_2_A Suspect O-H Bond in CIF: O2 -H21 .. 1.31 Ang.
| Author Response: The special geometry of the position of the enol hydrogen atom is
given in the table describing the hydrogen bonds.
|
Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ?
PLAT480_ALERT_4_C Long H...A H-Bond Reported H121 .. O1 .. 2.68 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H123 .. O3 .. 2.65 Ang.
Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
correct. If it is not, please give the correct count in the
_publ_section_exptl_refinement section of the submitted CIF.
From the CIF: _diffrn_reflns_theta_max 28.30
From the CIF: _reflns_number_total 1838
Count of symmetry unique reflns 1837
Completeness (_total/calc) 100.05%
TEST3: Check Friedels for noncentro structure
Estimate of Friedel pairs measured 1
Fraction of Friedel pairs measured 0.001
Are heavy atom types Z>Si present no
2 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
3 ALERT level C = Check and explain
1 ALERT level G = General alerts; check
1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
1 ALERT type 2 Indicator that the structure model may be wrong or deficient
1 ALERT type 3 Indicator that the structure quality may be low
3 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2000); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.
5-(4-methoxyphenyl)-1-phenylpent-4-ene-1,3-dione
top
Crystal data top
C18H16O3 | F(000) = 296 |
Mr = 280.31 | Dx = 1.334 Mg m−3 |
Monoclinic, P21 | Melting point = 393–394 K |
Hall symbol: P 2yb | Mo Kα radiation, λ = 0.71073 Å |
a = 3.9754 (8) Å | Cell parameters from 10099 reflections |
b = 9.790 (2) Å | θ = 2.1–28.4° |
c = 17.958 (4) Å | µ = 0.09 mm−1 |
β = 92.91 (3)° | T = 105 K |
V = 698.0 (3) Å3 | Plate, yellow |
Z = 2 | 0.4 × 0.4 × 0.1 mm |
Data collection top
Bruker SMART diffractometer | 1838 independent reflections |
Radiation source: fine-focus sealed tube | 1794 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.022 |
Detector resolution: 8 pixels mm-1 | θmax = 28.3°, θmin = 1.1° |
ω scans | h = −5→5 |
Absorption correction: multi-scan (SADABS; Sheldrick, 2002) | k = −13→13 |
Tmin = 0.965, Tmax = 0.991 | l = −23→23 |
11132 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)] = 0.028 | Hydrogen site location: difference Fourier map |
wR(F2) = 0.079 | All H-atom parameters refined |
S = 1.12 | w = 1/[σ2(Fo2) + (0.0881P)2 + 0.4691P] where P = (Fo2 + 2Fc2)/3 |
1838 reflections | (Δ/σ)max = 0.020 |
254 parameters | Δρmax = 0.24 e Å−3 |
1 restraint | Δρmin = −0.21 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 | |
O1 | 0.7478 (3) | 0.23595 (12) | 0.28853 (6) | 0.0277 (3) | |
O2 | 0.6016 (3) | 0.29013 (12) | 0.15712 (6) | 0.0309 (3) | |
O3 | 0.8910 (3) | 0.37033 (14) | 0.75071 (6) | 0.0271 (2) | |
C1 | 0.4700 (4) | 0.40322 (15) | 0.17643 (8) | 0.0220 (3) | |
C2 | 0.4670 (4) | 0.43937 (16) | 0.25299 (8) | 0.0216 (3) | |
H2 | 0.361 (5) | 0.522 (3) | 0.2661 (12) | 0.028 (5)* | |
C3 | 0.6085 (4) | 0.35162 (16) | 0.30711 (8) | 0.0215 (3) | |
C4 | 0.6079 (4) | 0.38521 (17) | 0.38649 (8) | 0.0221 (3) | |
H4 | 0.488 (6) | 0.467 (3) | 0.3969 (12) | 0.032 (5)* | |
C5 | 0.7587 (4) | 0.30436 (15) | 0.43892 (8) | 0.0213 (3) | |
H5 | 0.858 (5) | 0.223 (2) | 0.4223 (10) | 0.020 (4)* | |
C6 | 0.7792 (3) | 0.32671 (15) | 0.51963 (8) | 0.0199 (3) | |
C7 | 0.9452 (4) | 0.22908 (16) | 0.56558 (9) | 0.0228 (3) | |
H7 | 1.034 (5) | 0.154 (3) | 0.5430 (11) | 0.030 (5)* | |
C8 | 0.9768 (4) | 0.24602 (17) | 0.64229 (8) | 0.0234 (3) | |
H8 | 1.090 (5) | 0.182 (3) | 0.6734 (12) | 0.033 (5)* | |
C9 | 0.8427 (3) | 0.36190 (16) | 0.67501 (8) | 0.0215 (3) | |
C10 | 0.6743 (4) | 0.46067 (16) | 0.63072 (8) | 0.0220 (3) | |
H10 | 0.580 (5) | 0.543 (3) | 0.6536 (12) | 0.032 (5)* | |
C11 | 0.6444 (4) | 0.44191 (15) | 0.55375 (8) | 0.0213 (3) | |
H11 | 0.525 (6) | 0.516 (3) | 0.5259 (11) | 0.034 (6)* | |
C12 | 0.7318 (4) | 0.4814 (2) | 0.78748 (8) | 0.0283 (3) | |
H122 | 0.784 (6) | 0.465 (3) | 0.8432 (12) | 0.041 (6)* | |
H123 | 0.496 (6) | 0.479 (3) | 0.7785 (11) | 0.031 (5)* | |
H121 | 0.807 (6) | 0.567 (3) | 0.7704 (12) | 0.035 (6)* | |
C13 | 0.3293 (3) | 0.49390 (15) | 0.11628 (8) | 0.0201 (3) | |
C14 | 0.1465 (4) | 0.61172 (16) | 0.13135 (8) | 0.0233 (3) | |
H14 | 0.103 (5) | 0.638 (2) | 0.1817 (12) | 0.026 (5)* | |
C15 | 0.0218 (4) | 0.69481 (16) | 0.07341 (9) | 0.0260 (3) | |
C16 | 0.0827 (4) | 0.66171 (17) | −0.00027 (9) | 0.0251 (3) | |
H16 | −0.007 (6) | 0.720 (3) | −0.0395 (12) | 0.037 (6)* | |
H15 | −0.112 (5) | 0.773 (3) | 0.0841 (12) | 0.035 (6)* | |
C17 | 0.2669 (4) | 0.54523 (17) | −0.01551 (8) | 0.0245 (3) | |
H17 | 0.315 (5) | 0.525 (2) | −0.0671 (11) | 0.032 (5)* | |
C18 | 0.3876 (4) | 0.46115 (16) | 0.04206 (8) | 0.0227 (3) | |
H18 | 0.519 (5) | 0.382 (2) | 0.0312 (11) | 0.027 (5)* | |
H21 | 0.708 (10) | 0.243 (5) | 0.222 (2) | 0.110 (14)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0401 (6) | 0.0202 (5) | 0.0230 (5) | 0.0052 (5) | 0.0029 (4) | 0.0006 (4) |
O2 | 0.0493 (7) | 0.0215 (5) | 0.0223 (5) | 0.0085 (5) | 0.0046 (5) | −0.0006 (4) |
O3 | 0.0311 (5) | 0.0302 (6) | 0.0199 (5) | 0.0032 (5) | −0.0005 (4) | 0.0038 (4) |
C1 | 0.0241 (6) | 0.0202 (7) | 0.0219 (6) | −0.0016 (5) | 0.0028 (5) | 0.0005 (5) |
C2 | 0.0242 (6) | 0.0195 (7) | 0.0210 (6) | 0.0004 (6) | 0.0005 (5) | −0.0028 (5) |
C3 | 0.0220 (6) | 0.0203 (7) | 0.0224 (6) | −0.0024 (5) | 0.0025 (5) | −0.0012 (5) |
C4 | 0.0237 (6) | 0.0216 (7) | 0.0211 (6) | −0.0002 (6) | 0.0011 (5) | −0.0014 (6) |
C5 | 0.0207 (6) | 0.0202 (7) | 0.0231 (7) | −0.0022 (5) | 0.0024 (5) | −0.0009 (5) |
C6 | 0.0189 (6) | 0.0198 (7) | 0.0210 (6) | −0.0025 (5) | 0.0014 (5) | 0.0011 (5) |
C7 | 0.0217 (6) | 0.0201 (7) | 0.0267 (7) | 0.0010 (6) | 0.0025 (5) | 0.0019 (6) |
C8 | 0.0222 (6) | 0.0225 (7) | 0.0252 (7) | 0.0007 (6) | −0.0005 (5) | 0.0063 (6) |
C9 | 0.0203 (6) | 0.0232 (7) | 0.0210 (6) | −0.0032 (6) | 0.0007 (5) | 0.0035 (6) |
C10 | 0.0226 (6) | 0.0193 (7) | 0.0242 (7) | −0.0001 (5) | 0.0016 (5) | 0.0014 (5) |
C11 | 0.0213 (6) | 0.0190 (7) | 0.0236 (6) | 0.0013 (6) | 0.0005 (5) | 0.0041 (5) |
C12 | 0.0283 (7) | 0.0348 (9) | 0.0219 (7) | 0.0004 (7) | 0.0012 (5) | −0.0018 (7) |
C13 | 0.0216 (6) | 0.0179 (6) | 0.0207 (6) | −0.0033 (5) | 0.0016 (5) | 0.0002 (5) |
C14 | 0.0280 (7) | 0.0204 (7) | 0.0217 (6) | −0.0005 (6) | 0.0024 (5) | −0.0021 (6) |
C15 | 0.0288 (7) | 0.0206 (7) | 0.0286 (7) | 0.0010 (6) | 0.0012 (6) | 0.0005 (6) |
C16 | 0.0263 (7) | 0.0240 (7) | 0.0248 (7) | −0.0047 (6) | −0.0018 (6) | 0.0045 (6) |
C17 | 0.0256 (6) | 0.0280 (8) | 0.0199 (6) | −0.0055 (6) | 0.0017 (5) | −0.0002 (6) |
C18 | 0.0241 (6) | 0.0214 (7) | 0.0227 (6) | −0.0009 (6) | 0.0018 (5) | −0.0019 (6) |
Geometric parameters (Å, º) top
O1—C3 | 1.3110 (19) | C8—H8 | 0.94 (2) |
O1—H21 | 1.19 (4) | C9—C10 | 1.401 (2) |
O2—C1 | 1.2797 (19) | C10—C11 | 1.393 (2) |
O2—H21 | 1.31 (4) | C10—H10 | 0.99 (2) |
O3—C9 | 1.3657 (17) | C11—H11 | 0.99 (2) |
O3—C12 | 1.436 (2) | C12—H122 | 1.02 (2) |
C1—C2 | 1.4203 (19) | C12—H123 | 0.94 (2) |
C1—C13 | 1.485 (2) | C12—H121 | 0.95 (3) |
C2—C3 | 1.394 (2) | C13—C14 | 1.397 (2) |
C2—H2 | 0.94 (2) | C13—C18 | 1.4014 (19) |
C3—C4 | 1.4631 (19) | C14—C15 | 1.392 (2) |
C4—C5 | 1.347 (2) | C14—H14 | 0.97 (2) |
C4—H4 | 0.96 (3) | C15—C16 | 1.395 (2) |
C5—C6 | 1.4638 (19) | C15—H15 | 0.95 (2) |
C5—H5 | 0.94 (2) | C16—C17 | 1.390 (2) |
C6—C11 | 1.403 (2) | C16—H16 | 0.96 (2) |
C6—C7 | 1.405 (2) | C17—C18 | 1.388 (2) |
C7—C8 | 1.387 (2) | C17—H17 | 0.97 (2) |
C7—H7 | 0.92 (3) | C18—H18 | 0.96 (2) |
C8—C9 | 1.396 (2) | | |
| | | |
C3—O1—H21 | 100 (2) | C11—C10—C9 | 119.12 (13) |
C1—O2—H21 | 100 (2) | C11—C10—H10 | 120.4 (12) |
C9—O3—C12 | 117.43 (12) | C9—C10—H10 | 120.5 (12) |
O2—C1—C2 | 120.09 (14) | C10—C11—C6 | 121.60 (13) |
O2—C1—C13 | 117.65 (12) | C10—C11—H11 | 115.0 (13) |
C2—C1—C13 | 122.25 (13) | C6—C11—H11 | 123.4 (12) |
C3—C2—C1 | 119.89 (14) | O3—C12—H122 | 104.8 (15) |
C3—C2—H2 | 121.4 (13) | O3—C12—H123 | 111.2 (15) |
C1—C2—H2 | 118.7 (13) | H122—C12—H123 | 108.2 (18) |
O1—C3—C2 | 121.03 (13) | O3—C12—H121 | 111.6 (14) |
O1—C3—C4 | 117.63 (13) | H122—C12—H121 | 114 (2) |
C2—C3—C4 | 121.34 (14) | H123—C12—H121 | 107 (2) |
C5—C4—C3 | 121.74 (14) | C14—C13—C18 | 119.07 (13) |
C5—C4—H4 | 124.4 (13) | C14—C13—C1 | 122.21 (13) |
C3—C4—H4 | 113.9 (13) | C18—C13—C1 | 118.71 (13) |
C4—C5—C6 | 127.19 (14) | C15—C14—C13 | 120.44 (14) |
C4—C5—H5 | 117.0 (11) | C15—C14—H14 | 117.9 (13) |
C6—C5—H5 | 115.8 (11) | C13—C14—H14 | 121.7 (13) |
C11—C6—C7 | 117.95 (13) | C14—C15—C16 | 120.06 (14) |
C11—C6—C5 | 123.32 (13) | C14—C15—H15 | 119.8 (13) |
C7—C6—C5 | 118.72 (13) | C16—C15—H15 | 120.1 (13) |
C8—C7—C6 | 121.21 (14) | C17—C16—C15 | 119.72 (14) |
C8—C7—H7 | 121.2 (13) | C17—C16—H16 | 121.4 (14) |
C6—C7—H7 | 117.6 (13) | C15—C16—H16 | 118.9 (14) |
C7—C8—C9 | 119.87 (13) | C18—C17—C16 | 120.37 (14) |
C7—C8—H8 | 121.8 (14) | C18—C17—H17 | 120.8 (14) |
C9—C8—H8 | 118.4 (14) | C16—C17—H17 | 118.8 (14) |
O3—C9—C8 | 115.52 (13) | C17—C18—C13 | 120.33 (14) |
O3—C9—C10 | 124.23 (14) | C17—C18—H18 | 119.9 (12) |
C8—C9—C10 | 120.25 (13) | C13—C18—H18 | 119.7 (12) |
| | | |
O2—C1—C2—C3 | 0.2 (2) | C8—C9—C10—C11 | −0.3 (2) |
C13—C1—C2—C3 | −178.74 (13) | C9—C10—C11—C6 | −0.1 (2) |
C1—C2—C3—O1 | 0.5 (2) | C7—C6—C11—C10 | 0.4 (2) |
C1—C2—C3—C4 | −179.61 (13) | C5—C6—C11—C10 | −178.84 (13) |
O1—C3—C4—C5 | 3.2 (2) | O2—C1—C13—C14 | 172.53 (14) |
C2—C3—C4—C5 | −176.65 (14) | C2—C1—C13—C14 | −8.5 (2) |
C3—C4—C5—C6 | 179.36 (14) | O2—C1—C13—C18 | −8.7 (2) |
C4—C5—C6—C11 | −1.5 (2) | C2—C1—C13—C18 | 170.29 (13) |
C4—C5—C6—C7 | 179.25 (14) | C18—C13—C14—C15 | 0.5 (2) |
C11—C6—C7—C8 | −0.3 (2) | C1—C13—C14—C15 | 179.31 (14) |
C5—C6—C7—C8 | 178.98 (14) | C13—C14—C15—C16 | −0.8 (2) |
C6—C7—C8—C9 | −0.1 (2) | C14—C15—C16—C17 | 0.3 (2) |
C12—O3—C9—C8 | −174.56 (13) | C15—C16—C17—C18 | 0.6 (2) |
C12—O3—C9—C10 | 6.0 (2) | C16—C17—C18—C13 | −0.9 (2) |
C7—C8—C9—O3 | −179.07 (13) | C14—C13—C18—C17 | 0.4 (2) |
C7—C8—C9—C10 | 0.4 (2) | C1—C13—C18—C17 | −178.47 (13) |
O3—C9—C10—C11 | 179.12 (13) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C18—H18···C16i | 0.96 (2) | 2.75 (2) | 3.708 (2) | 178 (2) |
C12—H121···O1ii | 0.95 (3) | 2.68 (2) | 3.556 (2) | 154 (2) |
C12—H123···O3iii | 0.94 (2) | 2.65 (2) | 3.545 (2) | 158 (2) |
C10—H10···O1iv | 0.99 (2) | 2.55 (2) | 3.525 (2) | 172 (2) |
C14—H14···O3iv | 0.97 (2) | 2.57 (2) | 3.3089 (19) | 133 (2) |
O1—H21···O2 | 1.19 (4) | 1.31 (4) | 2.4594 (16) | 159 (4) |
Symmetry codes: (i) −x+1, y−1/2, −z; (ii) −x+2, y+1/2, −z+1; (iii) x−1, y, z; (iv) −x+1, y+1/2, −z+1. |