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The uncertainty associated with the position of one H atom in curcumin, C21H20O6, has been resolved by establishing the enol tautomeric form supported by an intra­molecular O—H...O hydrogen bond.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680700222X/bi2146sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680700222X/bi2146Isup2.hkl
Contains datablock I

CCDC reference: 636155

Key indicators

  • Single-crystal X-ray study
  • T = 290 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.062
  • wR factor = 0.143
  • Data-to-parameter ratio = 12.2

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT230_ALERT_2_B Hirshfeld Test Diff for O6 - C18 .. 12.46 su PLAT230_ALERT_2_B Hirshfeld Test Diff for C11 - C12 .. 7.94 su
Alert level C PLAT128_ALERT_4_C Non-standard setting of Space group P2/c .... P2/n PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5
0 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 2 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 2 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 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and CAMERON (Watkin et al., 1996); software used to prepare material for publication: PLATON (Spek, 2003).

(1E,4Z,6E)-5-hydroxy-1,7-bis(4-hydroxy-3-methoxyphenyl)hepta-1,4,6-trien-3-one top
Crystal data top
C21H20O6F(000) = 776
Mr = 368.37Dx = 1.348 Mg m3
Monoclinic, P2/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yacCell parameters from 564 reflections
a = 12.707 (3) Åθ = 1.8–25.0°
b = 7.2186 (14) ŵ = 0.10 mm1
c = 19.880 (4) ÅT = 290 K
β = 95.348 (4)°Block, orange
V = 1815.6 (7) Å30.30 × 0.25 × 0.20 mm
Z = 4
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
3152 independent reflections
Radiation source: fine-focus sealed tube1609 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.079
φ and ω scansθmax = 25.0°, θmin = 1.8°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1515
Tmin = 0.932, Tmax = 0.981k = 88
12396 measured reflectionsl = 2323
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)] = 0.062Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.143H atoms treated by a mixture of independent and constrained refinement
S = 0.99 w = 1/[σ2(Fo2) + (0.0574P)2]
where P = (Fo2 + 2Fc2)/3
3152 reflections(Δ/σ)max < 0.001
258 parametersΔρmax = 0.24 e Å3
0 restraintsΔρmin = 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
O11.44657 (19)0.3371 (4)0.40287 (15)0.0641 (8)
O20.79953 (19)0.1456 (3)0.41527 (11)0.0594 (7)
O30.63286 (18)0.1099 (4)0.46721 (13)0.0647 (8)
O40.3940 (3)0.1720 (5)0.86093 (14)0.0670 (9)
O51.37549 (17)0.3829 (3)0.52369 (12)0.0612 (7)
O60.3811 (2)0.1034 (4)0.76937 (13)0.0790 (9)
C11.3009 (3)0.3367 (4)0.47178 (17)0.0423 (9)
C21.3411 (3)0.3161 (4)0.40926 (19)0.0453 (9)
C31.2748 (3)0.2736 (4)0.35333 (18)0.0483 (9)
C41.1679 (3)0.2492 (4)0.35921 (18)0.0486 (9)
C51.1266 (2)0.2671 (4)0.42123 (17)0.0400 (8)
C61.1947 (2)0.3117 (4)0.47753 (17)0.0429 (8)
C71.0133 (3)0.2361 (4)0.42491 (17)0.0445 (9)
C80.9588 (3)0.2325 (4)0.47824 (18)0.0440 (9)
C90.8469 (3)0.1914 (4)0.47390 (17)0.0412 (8)
C100.7889 (3)0.1957 (4)0.52978 (17)0.0443 (9)
C110.6809 (3)0.1525 (4)0.52469 (18)0.0437 (9)
C120.6168 (3)0.1435 (5)0.5817 (2)0.0552 (10)
C130.6414 (3)0.2142 (5)0.6411 (2)0.0560 (10)
C140.5773 (3)0.1990 (5)0.69976 (19)0.0535 (10)
C150.5859 (3)0.3291 (5)0.7505 (2)0.0617 (11)
C160.5231 (3)0.3182 (5)0.80344 (19)0.0574 (10)
C170.4532 (3)0.1765 (5)0.80759 (18)0.0486 (9)
C180.4459 (3)0.0412 (5)0.75769 (18)0.0505 (9)
C190.5062 (3)0.0525 (5)0.70384 (17)0.0523 (10)
C210.3806 (4)0.2616 (6)0.7264 (2)0.0891 (14)
C231.3430 (3)0.3830 (5)0.58991 (18)0.0653 (11)
H31.30130.26100.31150.058*
H41.12300.22040.32100.058*
H61.16850.32480.51940.051*
H70.97410.21610.38370.053*
H80.99380.25740.52040.053*
H100.82260.22820.57170.053*
H120.55250.08160.57490.066*
H130.70450.28000.64760.067*
H150.63440.42520.74920.074*
H160.52860.40900.83680.069*
H190.49960.03720.67010.063*
H21A0.34430.23220.68320.134*
H21B0.34510.36220.74640.134*
H21C0.45200.29700.72060.134*
H23A1.28980.47600.59330.098*
H23B1.40260.40930.62180.098*
H23C1.31460.26370.59960.098*
H1O1.473 (3)0.343 (6)0.444 (2)0.091 (17)*
H4O0.364 (3)0.081 (6)0.8633 (19)0.073 (18)*
H230.704 (4)0.128 (6)0.426 (2)0.126 (16)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0345 (16)0.094 (2)0.063 (2)0.0019 (13)0.0076 (14)0.0047 (16)
O20.0365 (15)0.100 (2)0.0413 (15)0.0052 (13)0.0053 (12)0.0011 (13)
O30.0377 (15)0.103 (2)0.0521 (17)0.0111 (14)0.0046 (13)0.0033 (15)
O40.076 (2)0.075 (2)0.0529 (19)0.0015 (18)0.0247 (16)0.0073 (16)
O50.0406 (15)0.088 (2)0.0532 (17)0.0113 (13)0.0004 (13)0.0028 (13)
O60.081 (2)0.098 (2)0.0586 (18)0.0167 (17)0.0171 (15)0.0145 (16)
C10.036 (2)0.043 (2)0.047 (2)0.0032 (16)0.0027 (17)0.0042 (16)
C20.029 (2)0.047 (2)0.059 (3)0.0034 (16)0.0076 (18)0.0084 (18)
C30.037 (2)0.060 (3)0.047 (3)0.0028 (17)0.006 (2)0.0110 (19)
C40.039 (2)0.059 (2)0.045 (2)0.0053 (17)0.0056 (19)0.0063 (19)
C50.034 (2)0.046 (2)0.040 (2)0.0009 (15)0.0034 (17)0.0102 (16)
C60.036 (2)0.053 (2)0.043 (3)0.0010 (17)0.0095 (19)0.0035 (19)
C70.038 (2)0.052 (2)0.041 (2)0.0035 (16)0.004 (2)0.0084 (17)
C80.034 (2)0.057 (2)0.041 (2)0.0034 (16)0.0004 (19)0.0079 (18)
C90.040 (2)0.046 (2)0.037 (2)0.0001 (16)0.0026 (18)0.0051 (16)
C100.045 (2)0.050 (2)0.038 (2)0.0006 (18)0.0006 (19)0.0002 (18)
C110.042 (2)0.045 (2)0.046 (2)0.0028 (17)0.0166 (19)0.0101 (17)
C120.047 (3)0.056 (3)0.057 (3)0.001 (2)0.001 (2)0.003 (2)
C130.046 (3)0.050 (3)0.071 (3)0.000 (2)0.003 (2)0.005 (2)
C140.055 (3)0.052 (3)0.055 (3)0.0026 (19)0.013 (2)0.012 (2)
C150.068 (3)0.054 (3)0.062 (3)0.003 (2)0.014 (2)0.004 (2)
C160.065 (3)0.058 (3)0.050 (3)0.004 (2)0.014 (2)0.008 (2)
C170.051 (2)0.059 (3)0.037 (2)0.007 (2)0.0081 (19)0.0031 (19)
C180.050 (2)0.051 (2)0.050 (2)0.0074 (19)0.0050 (19)0.006 (2)
C190.062 (3)0.060 (3)0.036 (2)0.004 (2)0.009 (2)0.010 (2)
C210.098 (4)0.084 (3)0.082 (3)0.018 (3)0.008 (3)0.018 (3)
C230.052 (2)0.086 (3)0.054 (3)0.014 (2)0.008 (2)0.003 (2)
Geometric parameters (Å, º) top
O3—C111.282 (4)C14—C151.375 (5)
O3—H231.28 (5)C14—C191.398 (5)
O1—C21.366 (4)C14—C131.487 (5)
O1—H1O0.85 (4)C2—C31.366 (4)
O2—C91.303 (3)C3—C41.386 (4)
O2—H231.26 (5)C3—H30.930
O4—C171.356 (4)C12—C131.298 (4)
O4—H4O0.77 (4)C12—C111.458 (5)
O5—C11.375 (4)C12—H120.930
O5—C231.416 (4)C7—C81.320 (4)
O6—C181.363 (4)C7—H70.930
O6—C211.426 (4)C4—H40.930
C1—C61.377 (4)C8—H80.930
C1—C21.395 (4)C19—C181.375 (4)
C10—C91.390 (4)C19—H190.930
C10—C111.401 (4)C17—C161.362 (5)
C10—H100.930C17—C181.389 (4)
C9—C81.446 (4)C16—C151.381 (5)
C6—C51.387 (4)C16—H160.930
C6—H60.930C13—H130.930
C23—H23A0.960C15—H150.930
C23—H23B0.960C21—H21A0.960
C23—H23C0.960C21—H21B0.960
C5—C41.390 (4)C21—H21C0.960
C5—C71.466 (4)
C11—O3—H23104 (2)C11—C12—H12117.1
C2—O1—H1O103 (3)C8—C7—C5129.4 (3)
C9—O2—H23104.0 (19)C8—C7—H7115.3
C17—O4—H4O113 (3)C5—C7—H7115.3
C1—O5—C23117.2 (3)C3—C4—C5121.1 (3)
C18—O6—C21118.7 (3)C3—C4—H4119.4
O5—C1—C6125.5 (3)C5—C4—H4119.4
O5—C1—C2114.3 (3)C7—C8—C9122.8 (3)
C6—C1—C2120.2 (3)C7—C8—H8118.6
C9—C10—C11121.7 (3)C9—C8—H8118.6
C9—C10—H10119.1C18—C19—C14120.0 (3)
C11—C10—H10119.1C18—C19—H19120.0
O2—C9—C10119.0 (3)C14—C19—H19120.0
O2—C9—C8118.3 (3)O4—C17—C16118.5 (4)
C10—C9—C8122.6 (3)O4—C17—C18122.4 (4)
C1—C6—C5120.4 (3)C16—C17—C18119.0 (4)
C1—C6—H6119.8C17—C16—C15121.0 (4)
C5—C6—H6119.8C17—C16—H16119.5
O5—C23—H23A109.5C15—C16—H16119.5
O5—C23—H23B109.5C12—C13—C14125.5 (4)
H23A—C23—H23B109.5C12—C13—H13117.2
O5—C23—H23C109.5C14—C13—H13117.2
H23A—C23—H23C109.5O3—C11—C10120.0 (3)
H23B—C23—H23C109.5O3—C11—C12115.3 (3)
C6—C5—C4118.6 (3)C10—C11—C12124.6 (3)
C6—C5—C7122.5 (3)O6—C18—C19124.6 (4)
C4—C5—C7118.9 (3)O6—C18—C17114.7 (3)
C15—C14—C19118.8 (3)C19—C18—C17120.6 (4)
C15—C14—C13120.8 (4)C14—C15—C16120.5 (4)
C19—C14—C13120.4 (4)C14—C15—H15119.7
O1—C2—C3119.0 (3)C16—C15—H15119.7
O1—C2—C1121.0 (3)O6—C21—H21A109.5
C3—C2—C1120.0 (3)O6—C21—H21B109.5
C2—C3—C4119.7 (3)H21A—C21—H21B109.5
C2—C3—H3120.2O6—C21—H21C109.5
C4—C3—H3120.2H21A—C21—H21C109.5
C13—C12—C11125.8 (4)H21B—C21—H21C109.5
C13—C12—H12117.1
C23—O5—C1—C68.1 (5)C15—C14—C19—C180.4 (5)
C23—O5—C1—C2172.2 (3)C13—C14—C19—C18178.9 (3)
C11—C10—C9—O20.1 (5)O4—C17—C16—C15179.5 (3)
C11—C10—C9—C8178.9 (3)C18—C17—C16—C150.3 (5)
O5—C1—C6—C5179.2 (3)C11—C12—C13—C14177.7 (3)
C2—C1—C6—C50.4 (5)C15—C14—C13—C12155.2 (4)
C1—C6—C5—C40.3 (4)C19—C14—C13—C1224.1 (6)
C1—C6—C5—C7179.0 (3)C9—C10—C11—O31.0 (5)
O5—C1—C2—O11.5 (4)C9—C10—C11—C12176.2 (3)
C6—C1—C2—O1178.8 (3)C13—C12—C11—O3165.5 (3)
O5—C1—C2—C3178.8 (3)C13—C12—C11—C1017.3 (6)
C6—C1—C2—C30.9 (5)C21—O6—C18—C195.2 (5)
O1—C2—C3—C4179.1 (3)C21—O6—C18—C17170.8 (3)
C1—C2—C3—C40.7 (5)C14—C19—C18—O6174.2 (3)
C6—C5—C7—C84.6 (5)C14—C19—C18—C171.5 (5)
C4—C5—C7—C8174.7 (3)O4—C17—C18—O64.9 (5)
C2—C3—C4—C50.1 (5)C16—C17—C18—O6174.3 (3)
C6—C5—C4—C30.5 (5)O4—C17—C18—C19178.9 (3)
C7—C5—C4—C3178.7 (3)C16—C17—C18—C191.8 (5)
C5—C7—C8—C9177.1 (3)C19—C14—C15—C161.9 (5)
O2—C9—C8—C74.0 (5)C13—C14—C15—C16177.4 (3)
C10—C9—C8—C7177.1 (3)C17—C16—C15—C141.6 (6)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—H23···O21.28 (5)1.26 (6)2.455 (3)151 (5)
O2—H23···O31.26 (5)1.28 (5)2.455 (3)151 (3)
O1—H1O···O50.85 (4)2.13 (5)2.664 (5)121 (4)
O4—H4O···O60.77 (4)2.32 (6)2.690 (4)111 (3)
C7—H7···O6i0.932.593.512 (4)170
O4—H4O···O2ii0.77 (3)2.14 (4)2.848 (4)155 (5)
Symmetry codes: (i) x+1/2, y, z1/2; (ii) x1/2, y, z+1/2.
 

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