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In the crystal structure of the title compound, C19H20O6, the dihedral angle between the two aromatic planes is 31.8 (1)°. Intermolecular C—H...O hydrogen bonds serve to stabilize the structure.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805026292/bt6717sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805026292/bt6717Isup2.hkl
Contains datablock I

CCDC reference: 283762

Key indicators

  • Single-crystal X-ray study
  • T = 120 K
  • Mean [sigma](C-C) = 0.006 Å
  • R factor = 0.050
  • wR factor = 0.088
  • Data-to-parameter ratio = 8.5

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 6 PLAT432_ALERT_2_C Short Inter X...Y Contact O2 .. C16 .. 3.00 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 28.08 From the CIF: _reflns_number_total 1954 Count of symmetry unique reflns 1957 Completeness (_total/calc) 99.85% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 0 Fraction of Friedel pairs measured 0.000 Are heavy atom types Z>Si present no
0 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 0 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 2 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Bruker, 2002); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

2'-Hydroxy-4,4',5',6'-tetramethoxychalcone top
Crystal data top
C19H20O6F(000) = 728
Mr = 344.35Dx = 1.423 Mg m3
Monoclinic, CcMo Kα radiation, λ = 0.71073 Å
a = 13.092 (4) ÅCell parameters from 1038 reflections
b = 15.041 (5) Åθ = 2.7–22.4°
c = 8.256 (3) ŵ = 0.11 mm1
β = 98.649 (7)°T = 120 K
V = 1607.3 (9) Å3Prism, yellow
Z = 40.48 × 0.20 × 0.18 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer
1954 independent reflections
Radiation source: sealed tube1346 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.068
φ and ω scansθmax = 28.1°, θmin = 2.1°
Absorption correction: multi-scan
(SADABS; Bruker, 2002)
h = 1717
Tmin = 0.951, Tmax = 0.978k = 1919
7488 measured reflectionsl = 1010
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)] = 0.050Hydrogen site location: difference Fourier map
wR(F2) = 0.088H-atom parameters constrained
S = 0.91 w = 1/[σ2(Fo2) + (0.0277P)2]
where P = (Fo2 + 2Fc2)/3
1954 reflections(Δ/σ)max < 0.001
231 parametersΔρmax = 0.23 e Å3
2 restraintsΔρmin = 0.29 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
O10.28657 (19)0.09265 (18)0.4913 (3)0.0394 (8)
O20.88884 (19)0.13248 (17)0.9338 (3)0.0292 (7)
O31.04942 (19)0.10618 (15)1.1233 (3)0.0295 (7)
H31.00710.13451.05590.044*
O41.13136 (19)0.18490 (17)1.3040 (3)0.0300 (7)
O50.95605 (18)0.24797 (17)1.1318 (3)0.0294 (7)
O60.82109 (18)0.13873 (17)0.9579 (3)0.0241 (6)
C10.2463 (3)0.1666 (3)0.3970 (6)0.0389 (11)
H1A0.26470.22140.45860.058*
H1B0.17090.16150.37260.058*
H1C0.27530.16800.29430.058*
C20.3886 (3)0.0949 (3)0.5532 (5)0.0261 (9)
C30.4220 (3)0.0299 (3)0.6666 (5)0.0320 (10)
H3A0.37460.01310.69500.038*
C40.5232 (3)0.0274 (2)0.7384 (5)0.0268 (9)
H4A0.54540.01730.81730.032*
C50.5935 (3)0.0890 (2)0.6974 (5)0.0249 (9)
C60.5579 (3)0.1530 (2)0.5820 (5)0.0275 (9)
H6A0.60520.19570.55210.033*
C70.4569 (3)0.1566 (3)0.5097 (5)0.0282 (10)
H7A0.43430.20110.43070.034*
C80.7007 (3)0.0924 (3)0.7733 (5)0.0268 (9)
H8A0.74020.14030.74060.032*
C90.7508 (3)0.0365 (3)0.8834 (5)0.0268 (9)
H9A0.71730.01440.91860.032*
C100.8579 (3)0.0558 (3)0.9479 (5)0.0255 (9)
C110.9293 (3)0.0101 (3)1.0344 (4)0.0219 (9)
C121.0221 (3)0.0197 (2)1.1214 (5)0.0251 (9)
C131.0904 (3)0.0365 (3)1.2138 (5)0.0257 (9)
H13A1.15180.01351.27550.031*
C141.0700 (3)0.1250 (3)1.2165 (5)0.0260 (10)
C151.2228 (3)0.1518 (3)1.4008 (5)0.0323 (10)
H15A1.26770.12521.32920.048*
H15B1.25920.20071.46310.048*
H15C1.20420.10661.47690.048*
C160.9798 (3)0.1599 (3)1.1252 (5)0.0238 (8)
C171.0127 (3)0.3024 (3)1.0360 (6)0.0411 (11)
H17A1.00420.27970.92350.062*
H17B0.98690.36351.03560.062*
H17C1.08600.30131.08290.062*
C180.9112 (3)0.1021 (3)1.0383 (5)0.0232 (9)
C190.8222 (3)0.1532 (3)0.7888 (5)0.0358 (10)
H19A0.83920.09760.73720.054*
H19B0.75410.17390.73730.054*
H19C0.87430.19830.77490.054*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0269 (16)0.0374 (18)0.051 (2)0.0007 (13)0.0041 (15)0.0022 (15)
O20.0316 (16)0.0270 (15)0.0290 (17)0.0022 (13)0.0048 (13)0.0050 (13)
O30.0264 (16)0.0229 (14)0.0367 (19)0.0031 (12)0.0031 (13)0.0047 (13)
O40.0293 (15)0.0279 (15)0.0310 (17)0.0038 (13)0.0009 (13)0.0026 (13)
O50.0326 (15)0.0236 (14)0.0326 (17)0.0003 (12)0.0071 (13)0.0010 (12)
O60.0239 (14)0.0281 (14)0.0200 (15)0.0039 (12)0.0022 (12)0.0002 (12)
C10.032 (2)0.036 (2)0.043 (3)0.007 (2)0.009 (2)0.008 (2)
C20.020 (2)0.030 (2)0.028 (2)0.0025 (18)0.0018 (18)0.0048 (19)
C30.028 (2)0.029 (2)0.038 (3)0.0032 (18)0.006 (2)0.005 (2)
C40.029 (2)0.023 (2)0.028 (2)0.0043 (17)0.0019 (18)0.0074 (17)
C50.029 (2)0.023 (2)0.023 (2)0.0034 (18)0.0066 (18)0.0006 (17)
C60.029 (2)0.025 (2)0.029 (2)0.0034 (17)0.0056 (19)0.0017 (18)
C70.033 (2)0.028 (2)0.022 (2)0.0077 (18)0.0000 (18)0.0035 (18)
C80.032 (2)0.028 (2)0.023 (2)0.0006 (18)0.0117 (18)0.0016 (18)
C90.029 (2)0.027 (2)0.026 (2)0.0028 (18)0.0075 (18)0.0037 (19)
C100.031 (2)0.029 (2)0.019 (2)0.0024 (18)0.0099 (18)0.0039 (18)
C110.024 (2)0.026 (2)0.016 (2)0.0017 (17)0.0055 (17)0.0010 (16)
C120.027 (2)0.026 (2)0.024 (2)0.0030 (18)0.0098 (19)0.0042 (18)
C130.022 (2)0.029 (2)0.026 (2)0.0013 (17)0.0016 (18)0.0028 (18)
C140.029 (2)0.025 (2)0.026 (2)0.0046 (18)0.010 (2)0.0019 (17)
C150.029 (2)0.036 (2)0.032 (3)0.0079 (19)0.003 (2)0.002 (2)
C160.026 (2)0.022 (2)0.025 (2)0.0018 (17)0.0068 (17)0.0002 (18)
C170.046 (3)0.030 (2)0.048 (3)0.001 (2)0.009 (2)0.009 (2)
C180.022 (2)0.028 (2)0.020 (2)0.0007 (18)0.0043 (17)0.0017 (18)
C190.041 (2)0.043 (2)0.021 (2)0.012 (2)0.0005 (19)0.008 (2)
Geometric parameters (Å, º) top
O1—C21.357 (4)C6—H6A0.9500
O1—C11.414 (5)C7—H7A0.9500
O2—C101.234 (4)C8—C91.336 (5)
O3—C121.349 (4)C8—H8A0.9500
O3—H30.8400C9—C101.453 (5)
O4—C141.344 (5)C9—H9A0.9500
O4—C151.425 (5)C10—C111.471 (5)
O5—C161.364 (4)C11—C121.390 (5)
O5—C171.422 (4)C11—C181.404 (5)
O6—C181.379 (4)C12—C131.375 (5)
O6—C191.415 (4)C13—C141.358 (5)
C1—H1A0.9800C13—H13A0.9500
C1—H1B0.9800C14—C161.404 (5)
C1—H1C0.9800C15—H15A0.9800
C2—C71.373 (5)C15—H15B0.9800
C2—C31.378 (5)C15—H15C0.9800
C3—C41.368 (5)C16—C181.372 (5)
C3—H3A0.9500C17—H17A0.9800
C4—C51.384 (5)C17—H17B0.9800
C4—H4A0.9500C17—H17C0.9800
C5—C61.385 (5)C19—H19A0.9800
C5—C81.449 (5)C19—H19B0.9800
C6—C71.368 (5)C19—H19C0.9800
C2—O1—C1116.9 (3)C9—C10—C11123.4 (4)
C12—O3—H3109.5C12—C11—C18116.3 (3)
C14—O4—C15116.8 (3)C12—C11—C10118.4 (3)
C16—O5—C17113.3 (3)C18—C11—C10125.3 (3)
C18—O6—C19113.7 (3)O3—C12—C13115.9 (3)
O1—C1—H1A109.5O3—C12—C11121.8 (3)
O1—C1—H1B109.5C13—C12—C11122.3 (3)
H1A—C1—H1B109.5C14—C13—C12119.9 (4)
O1—C1—H1C109.5C14—C13—H13A120.1
H1A—C1—H1C109.5C12—C13—H13A120.1
H1B—C1—H1C109.5O4—C14—C13124.3 (4)
O1—C2—C7124.1 (4)O4—C14—C16115.1 (3)
O1—C2—C3115.5 (3)C13—C14—C16120.6 (4)
C7—C2—C3120.3 (3)O4—C15—H15A109.5
C4—C3—C2120.1 (4)O4—C15—H15B109.5
C4—C3—H3A120.0H15A—C15—H15B109.5
C2—C3—H3A120.0O4—C15—H15C109.5
C3—C4—C5120.8 (4)H15A—C15—H15C109.5
C3—C4—H4A119.6H15B—C15—H15C109.5
C5—C4—H4A119.6O5—C16—C18120.1 (4)
C4—C5—C6117.8 (3)O5—C16—C14121.3 (3)
C4—C5—C8123.7 (3)C18—C16—C14118.4 (3)
C6—C5—C8118.5 (3)O5—C17—H17A109.5
C7—C6—C5122.1 (4)O5—C17—H17B109.5
C7—C6—H6A119.0H17A—C17—H17B109.5
C5—C6—H6A119.0O5—C17—H17C109.5
C6—C7—C2118.9 (4)H17A—C17—H17C109.5
C6—C7—H7A120.5H17B—C17—H17C109.5
C2—C7—H7A120.5C16—C18—O6116.3 (3)
C9—C8—C5128.1 (4)C16—C18—C11122.5 (3)
C9—C8—H8A116.0O6—C18—C11121.2 (3)
C5—C8—H8A116.0O6—C19—H19A109.5
C8—C9—C10118.2 (4)O6—C19—H19B109.5
C8—C9—H9A120.9H19A—C19—H19B109.5
C10—C9—H9A120.9O6—C19—H19C109.5
O2—C10—C9117.7 (4)H19A—C19—H19C109.5
O2—C10—C11118.9 (4)H19B—C19—H19C109.5
C1—O1—C2—C710.4 (6)C10—C11—C12—C13176.0 (4)
C1—O1—C2—C3169.4 (3)O3—C12—C13—C14178.8 (3)
O1—C2—C3—C4178.9 (3)C11—C12—C13—C142.7 (6)
C7—C2—C3—C40.9 (6)C15—O4—C14—C130.8 (5)
C2—C3—C4—C50.6 (6)C15—O4—C14—C16178.9 (3)
C3—C4—C5—C60.0 (6)C12—C13—C14—O4179.3 (4)
C3—C4—C5—C8177.4 (4)C12—C13—C14—C160.3 (6)
C4—C5—C6—C70.2 (6)C17—O5—C16—C18106.9 (4)
C8—C5—C6—C7177.3 (4)C17—O5—C16—C1478.3 (5)
C5—C6—C7—C20.1 (6)O4—C14—C16—O52.4 (5)
O1—C2—C7—C6179.2 (4)C13—C14—C16—O5177.3 (4)
C3—C2—C7—C60.7 (6)O4—C14—C16—C18177.2 (3)
C4—C5—C8—C94.4 (6)C13—C14—C16—C182.4 (6)
C6—C5—C8—C9178.3 (4)O5—C16—C18—O61.6 (5)
C5—C8—C9—C10177.3 (4)C14—C16—C18—O6176.5 (3)
C8—C9—C10—O219.2 (5)O5—C16—C18—C11176.6 (3)
C8—C9—C10—C11163.4 (3)C14—C16—C18—C111.7 (6)
O2—C10—C11—C1211.2 (5)C19—O6—C18—C1699.6 (4)
C9—C10—C11—C12166.1 (3)C19—O6—C18—C1182.3 (4)
O2—C10—C11—C18169.5 (3)C12—C11—C18—C161.1 (5)
C9—C10—C11—C1813.1 (6)C10—C11—C18—C16178.2 (4)
C18—C11—C12—O3178.2 (4)C12—C11—C18—O6179.2 (3)
C10—C11—C12—O32.5 (5)C10—C11—C18—O60.1 (5)
C18—C11—C12—C133.3 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—H3···O20.841.722.457 (4)146
C9—H9A···O60.952.312.829 (4)114
C7—H7A···O2i0.952.573.329 (5)137
C1—H1B···O3ii0.982.543.289 (5)133
C15—H15B···O6iii0.982.553.410 (5)147
C15—H15C···O3iv0.982.513.201 (5)127
Symmetry codes: (i) x1/2, y+1/2, z1/2; (ii) x1, y, z1; (iii) x+1/2, y1/2, z+1/2; (iv) x, y, z+1/2.
 

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