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The title mol­ecule, C18H16O3, 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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805026140/er6020sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805026140/er6020Isup2.hkl
Contains datablock I

CCDC reference: 283909

Key indicators

  • Single-crystal X-ray study
  • T = 105 K
  • Mean [sigma](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

Computing details top

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
C18H16O3F(000) = 296
Mr = 280.31Dx = 1.334 Mg m3
Monoclinic, P21Melting point = 393–394 K
Hall symbol: P 2ybMo Kα radiation, λ = 0.71073 Å
a = 3.9754 (8) ÅCell parameters from 10099 reflections
b = 9.790 (2) Åθ = 2.1–28.4°
c = 17.958 (4) ŵ = 0.09 mm1
β = 92.91 (3)°T = 105 K
V = 698.0 (3) Å3Plate, yellow
Z = 20.4 × 0.4 × 0.1 mm
Data collection top
Bruker SMART
diffractometer
1838 independent reflections
Radiation source: fine-focus sealed tube1794 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.022
Detector resolution: 8 pixels mm-1θmax = 28.3°, θmin = 1.1°
ω scansh = 55
Absorption correction: multi-scan
(SADABS; Sheldrick, 2002)
k = 1313
Tmin = 0.965, Tmax = 0.991l = 2323
11132 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)] = 0.028Hydrogen site location: difference Fourier map
wR(F2) = 0.079All 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 parametersΔρmax = 0.24 e Å3
1 restraintΔρmin = 0.21 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
O10.7478 (3)0.23595 (12)0.28853 (6)0.0277 (3)
O20.6016 (3)0.29013 (12)0.15712 (6)0.0309 (3)
O30.8910 (3)0.37033 (14)0.75071 (6)0.0271 (2)
C10.4700 (4)0.40322 (15)0.17643 (8)0.0220 (3)
C20.4670 (4)0.43937 (16)0.25299 (8)0.0216 (3)
H20.361 (5)0.522 (3)0.2661 (12)0.028 (5)*
C30.6085 (4)0.35162 (16)0.30711 (8)0.0215 (3)
C40.6079 (4)0.38521 (17)0.38649 (8)0.0221 (3)
H40.488 (6)0.467 (3)0.3969 (12)0.032 (5)*
C50.7587 (4)0.30436 (15)0.43892 (8)0.0213 (3)
H50.858 (5)0.223 (2)0.4223 (10)0.020 (4)*
C60.7792 (3)0.32671 (15)0.51963 (8)0.0199 (3)
C70.9452 (4)0.22908 (16)0.56558 (9)0.0228 (3)
H71.034 (5)0.154 (3)0.5430 (11)0.030 (5)*
C80.9768 (4)0.24602 (17)0.64229 (8)0.0234 (3)
H81.090 (5)0.182 (3)0.6734 (12)0.033 (5)*
C90.8427 (3)0.36190 (16)0.67501 (8)0.0215 (3)
C100.6743 (4)0.46067 (16)0.63072 (8)0.0220 (3)
H100.580 (5)0.543 (3)0.6536 (12)0.032 (5)*
C110.6444 (4)0.44191 (15)0.55375 (8)0.0213 (3)
H110.525 (6)0.516 (3)0.5259 (11)0.034 (6)*
C120.7318 (4)0.4814 (2)0.78748 (8)0.0283 (3)
H1220.784 (6)0.465 (3)0.8432 (12)0.041 (6)*
H1230.496 (6)0.479 (3)0.7785 (11)0.031 (5)*
H1210.807 (6)0.567 (3)0.7704 (12)0.035 (6)*
C130.3293 (3)0.49390 (15)0.11628 (8)0.0201 (3)
C140.1465 (4)0.61172 (16)0.13135 (8)0.0233 (3)
H140.103 (5)0.638 (2)0.1817 (12)0.026 (5)*
C150.0218 (4)0.69481 (16)0.07341 (9)0.0260 (3)
C160.0827 (4)0.66171 (17)0.00027 (9)0.0251 (3)
H160.007 (6)0.720 (3)0.0395 (12)0.037 (6)*
H150.112 (5)0.773 (3)0.0841 (12)0.035 (6)*
C170.2669 (4)0.54523 (17)0.01551 (8)0.0245 (3)
H170.315 (5)0.525 (2)0.0671 (11)0.032 (5)*
C180.3876 (4)0.46115 (16)0.04206 (8)0.0227 (3)
H180.519 (5)0.382 (2)0.0312 (11)0.027 (5)*
H210.708 (10)0.243 (5)0.222 (2)0.110 (14)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0401 (6)0.0202 (5)0.0230 (5)0.0052 (5)0.0029 (4)0.0006 (4)
O20.0493 (7)0.0215 (5)0.0223 (5)0.0085 (5)0.0046 (5)0.0006 (4)
O30.0311 (5)0.0302 (6)0.0199 (5)0.0032 (5)0.0005 (4)0.0038 (4)
C10.0241 (6)0.0202 (7)0.0219 (6)0.0016 (5)0.0028 (5)0.0005 (5)
C20.0242 (6)0.0195 (7)0.0210 (6)0.0004 (6)0.0005 (5)0.0028 (5)
C30.0220 (6)0.0203 (7)0.0224 (6)0.0024 (5)0.0025 (5)0.0012 (5)
C40.0237 (6)0.0216 (7)0.0211 (6)0.0002 (6)0.0011 (5)0.0014 (6)
C50.0207 (6)0.0202 (7)0.0231 (7)0.0022 (5)0.0024 (5)0.0009 (5)
C60.0189 (6)0.0198 (7)0.0210 (6)0.0025 (5)0.0014 (5)0.0011 (5)
C70.0217 (6)0.0201 (7)0.0267 (7)0.0010 (6)0.0025 (5)0.0019 (6)
C80.0222 (6)0.0225 (7)0.0252 (7)0.0007 (6)0.0005 (5)0.0063 (6)
C90.0203 (6)0.0232 (7)0.0210 (6)0.0032 (6)0.0007 (5)0.0035 (6)
C100.0226 (6)0.0193 (7)0.0242 (7)0.0001 (5)0.0016 (5)0.0014 (5)
C110.0213 (6)0.0190 (7)0.0236 (6)0.0013 (6)0.0005 (5)0.0041 (5)
C120.0283 (7)0.0348 (9)0.0219 (7)0.0004 (7)0.0012 (5)0.0018 (7)
C130.0216 (6)0.0179 (6)0.0207 (6)0.0033 (5)0.0016 (5)0.0002 (5)
C140.0280 (7)0.0204 (7)0.0217 (6)0.0005 (6)0.0024 (5)0.0021 (6)
C150.0288 (7)0.0206 (7)0.0286 (7)0.0010 (6)0.0012 (6)0.0005 (6)
C160.0263 (7)0.0240 (7)0.0248 (7)0.0047 (6)0.0018 (6)0.0045 (6)
C170.0256 (6)0.0280 (8)0.0199 (6)0.0055 (6)0.0017 (5)0.0002 (6)
C180.0241 (6)0.0214 (7)0.0227 (6)0.0009 (6)0.0018 (5)0.0019 (6)
Geometric parameters (Å, º) top
O1—C31.3110 (19)C8—H80.94 (2)
O1—H211.19 (4)C9—C101.401 (2)
O2—C11.2797 (19)C10—C111.393 (2)
O2—H211.31 (4)C10—H100.99 (2)
O3—C91.3657 (17)C11—H110.99 (2)
O3—C121.436 (2)C12—H1221.02 (2)
C1—C21.4203 (19)C12—H1230.94 (2)
C1—C131.485 (2)C12—H1210.95 (3)
C2—C31.394 (2)C13—C141.397 (2)
C2—H20.94 (2)C13—C181.4014 (19)
C3—C41.4631 (19)C14—C151.392 (2)
C4—C51.347 (2)C14—H140.97 (2)
C4—H40.96 (3)C15—C161.395 (2)
C5—C61.4638 (19)C15—H150.95 (2)
C5—H50.94 (2)C16—C171.390 (2)
C6—C111.403 (2)C16—H160.96 (2)
C6—C71.405 (2)C17—C181.388 (2)
C7—C81.387 (2)C17—H170.97 (2)
C7—H70.92 (3)C18—H180.96 (2)
C8—C91.396 (2)
C3—O1—H21100 (2)C11—C10—C9119.12 (13)
C1—O2—H21100 (2)C11—C10—H10120.4 (12)
C9—O3—C12117.43 (12)C9—C10—H10120.5 (12)
O2—C1—C2120.09 (14)C10—C11—C6121.60 (13)
O2—C1—C13117.65 (12)C10—C11—H11115.0 (13)
C2—C1—C13122.25 (13)C6—C11—H11123.4 (12)
C3—C2—C1119.89 (14)O3—C12—H122104.8 (15)
C3—C2—H2121.4 (13)O3—C12—H123111.2 (15)
C1—C2—H2118.7 (13)H122—C12—H123108.2 (18)
O1—C3—C2121.03 (13)O3—C12—H121111.6 (14)
O1—C3—C4117.63 (13)H122—C12—H121114 (2)
C2—C3—C4121.34 (14)H123—C12—H121107 (2)
C5—C4—C3121.74 (14)C14—C13—C18119.07 (13)
C5—C4—H4124.4 (13)C14—C13—C1122.21 (13)
C3—C4—H4113.9 (13)C18—C13—C1118.71 (13)
C4—C5—C6127.19 (14)C15—C14—C13120.44 (14)
C4—C5—H5117.0 (11)C15—C14—H14117.9 (13)
C6—C5—H5115.8 (11)C13—C14—H14121.7 (13)
C11—C6—C7117.95 (13)C14—C15—C16120.06 (14)
C11—C6—C5123.32 (13)C14—C15—H15119.8 (13)
C7—C6—C5118.72 (13)C16—C15—H15120.1 (13)
C8—C7—C6121.21 (14)C17—C16—C15119.72 (14)
C8—C7—H7121.2 (13)C17—C16—H16121.4 (14)
C6—C7—H7117.6 (13)C15—C16—H16118.9 (14)
C7—C8—C9119.87 (13)C18—C17—C16120.37 (14)
C7—C8—H8121.8 (14)C18—C17—H17120.8 (14)
C9—C8—H8118.4 (14)C16—C17—H17118.8 (14)
O3—C9—C8115.52 (13)C17—C18—C13120.33 (14)
O3—C9—C10124.23 (14)C17—C18—H18119.9 (12)
C8—C9—C10120.25 (13)C13—C18—H18119.7 (12)
O2—C1—C2—C30.2 (2)C8—C9—C10—C110.3 (2)
C13—C1—C2—C3178.74 (13)C9—C10—C11—C60.1 (2)
C1—C2—C3—O10.5 (2)C7—C6—C11—C100.4 (2)
C1—C2—C3—C4179.61 (13)C5—C6—C11—C10178.84 (13)
O1—C3—C4—C53.2 (2)O2—C1—C13—C14172.53 (14)
C2—C3—C4—C5176.65 (14)C2—C1—C13—C148.5 (2)
C3—C4—C5—C6179.36 (14)O2—C1—C13—C188.7 (2)
C4—C5—C6—C111.5 (2)C2—C1—C13—C18170.29 (13)
C4—C5—C6—C7179.25 (14)C18—C13—C14—C150.5 (2)
C11—C6—C7—C80.3 (2)C1—C13—C14—C15179.31 (14)
C5—C6—C7—C8178.98 (14)C13—C14—C15—C160.8 (2)
C6—C7—C8—C90.1 (2)C14—C15—C16—C170.3 (2)
C12—O3—C9—C8174.56 (13)C15—C16—C17—C180.6 (2)
C12—O3—C9—C106.0 (2)C16—C17—C18—C130.9 (2)
C7—C8—C9—O3179.07 (13)C14—C13—C18—C170.4 (2)
C7—C8—C9—C100.4 (2)C1—C13—C18—C17178.47 (13)
O3—C9—C10—C11179.12 (13)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C18—H18···C16i0.96 (2)2.75 (2)3.708 (2)178 (2)
C12—H121···O1ii0.95 (3)2.68 (2)3.556 (2)154 (2)
C12—H123···O3iii0.94 (2)2.65 (2)3.545 (2)158 (2)
C10—H10···O1iv0.99 (2)2.55 (2)3.525 (2)172 (2)
C14—H14···O3iv0.97 (2)2.57 (2)3.3089 (19)133 (2)
O1—H21···O21.19 (4)1.31 (4)2.4594 (16)159 (4)
Symmetry codes: (i) x+1, y1/2, z; (ii) x+2, y+1/2, z+1; (iii) x1, y, z; (iv) x+1, y+1/2, z+1.
 

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