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The title compound, C17H14O4, a homoisoflavanoid, was isolated from the twigs and stems of Caesalpinia digyna Rottler. The pyran ring adopts an envelope conformation. The symmetry-related mol­ecules are linked via O—H...O and C—H...O inter­molecular hydrogen bonds to form a mol­ecular network.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805034823/ci6686sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805034823/ci6686Isup2.hkl
Contains datablock I

CCDC reference: 290010

Key indicators

  • Single-crystal X-ray study
  • T = 297 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.044
  • wR factor = 0.106
  • Data-to-parameter ratio = 13.5

checkCIF/PLATON results

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Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ?
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion
checkCIF publication errors
Alert level A PUBL024_ALERT_1_A The number of authors is greater than 5. Please specify the role of each of the co-authors for your paper.
1 ALERT level A = Data missing that is essential or data in wrong format 0 ALERT level G = General alerts. Data that may be required is missing

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003).

2,3-dihydro-7-hydroxy-3-[(4-methoxyphenyl)methylene]-4H-1-benzopyran-4-one top
Crystal data top
C17H14O4F(000) = 592
Mr = 282.28Dx = 1.416 Mg m3
Monoclinic, P21/cMelting point = 488–490 K
Hall symbol: -P 2ybcMo Kα radiation, λ = 0.71073 Å
a = 3.9591 (11) ÅCell parameters from 2593 reflections
b = 20.939 (5) Åθ = 1.6–26.0°
c = 16.209 (4) ŵ = 0.10 mm1
β = 99.844 (7)°T = 297 K
V = 1323.9 (6) Å3Needle, colourless
Z = 40.55 × 0.05 × 0.04 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer
2593 independent reflections
Radiation source: fine-focus sealed tube1997 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.036
Detector resolution: 8.33 pixels mm-1θmax = 26.0°, θmin = 1.6°
ω scansh = 44
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
k = 2525
Tmin = 0.994, Tmax = 0.996l = 1919
13570 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)] = 0.044Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.106H-atom parameters constrained
S = 1.08 w = 1/[σ2(Fo2) + (0.0414P)2 + 0.4026P]
where P = (Fo2 + 2Fc2)/3
2593 reflections(Δ/σ)max = 0.001
192 parametersΔρmax = 0.19 e Å3
0 restraintsΔρmin = 0.15 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
O10.3373 (3)0.07801 (6)0.48932 (7)0.0408 (3)
O20.0199 (4)0.22947 (6)0.61048 (8)0.0510 (4)
O30.1600 (4)0.18424 (6)0.23273 (8)0.0539 (4)
H30.08680.21760.20990.081*
O40.6640 (4)0.07164 (6)0.93901 (8)0.0477 (4)
C10.2102 (4)0.13093 (8)0.44565 (10)0.0316 (4)
C20.2405 (5)0.13278 (8)0.36196 (11)0.0366 (4)
H20.33930.09870.33790.044*
C30.1228 (5)0.18561 (8)0.31405 (10)0.0361 (4)
C40.0270 (5)0.23666 (8)0.34969 (11)0.0396 (4)
H40.11030.27170.31720.047*
C50.0503 (5)0.23473 (8)0.43306 (11)0.0372 (4)
H50.14720.26920.45680.045*
C60.0683 (4)0.18215 (8)0.48366 (10)0.0313 (4)
C70.0689 (5)0.18208 (8)0.57403 (11)0.0344 (4)
C80.1856 (5)0.12225 (8)0.61888 (10)0.0328 (4)
C90.2010 (5)0.06451 (8)0.56462 (10)0.0368 (4)
H9A0.34250.03220.59670.044*
H9B0.02810.04710.54920.044*
C100.2689 (5)0.12230 (8)0.70259 (11)0.0378 (4)
H100.26310.16220.72760.045*
C110.3674 (5)0.06956 (8)0.76064 (10)0.0352 (4)
C120.5836 (5)0.08131 (9)0.83691 (11)0.0415 (5)
H120.66370.12260.84910.050*
C130.6803 (5)0.03373 (9)0.89399 (11)0.0419 (5)
H130.82940.04260.94350.050*
C140.5560 (5)0.02776 (9)0.87797 (10)0.0359 (4)
C150.3348 (5)0.04092 (9)0.80379 (11)0.0377 (4)
H150.24760.08190.79300.045*
C160.2451 (5)0.00749 (9)0.74601 (11)0.0372 (4)
H160.09940.00170.69610.045*
C170.4982 (6)0.13247 (9)0.93384 (13)0.0497 (5)
H17A0.58640.15720.98270.075*
H17B0.54100.15450.88470.075*
H17C0.25580.12660.93060.075*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0578 (8)0.0361 (7)0.0306 (7)0.0160 (6)0.0132 (6)0.0047 (5)
O20.0820 (11)0.0365 (7)0.0344 (7)0.0126 (7)0.0093 (7)0.0068 (6)
O30.0882 (12)0.0466 (8)0.0290 (7)0.0089 (8)0.0159 (7)0.0066 (6)
O40.0529 (9)0.0489 (8)0.0387 (8)0.0016 (6)0.0005 (6)0.0122 (6)
C10.0358 (10)0.0279 (9)0.0300 (9)0.0006 (7)0.0024 (7)0.0002 (7)
C20.0458 (11)0.0332 (10)0.0316 (9)0.0024 (8)0.0092 (8)0.0036 (7)
C30.0460 (11)0.0364 (10)0.0254 (9)0.0049 (8)0.0050 (8)0.0007 (7)
C40.0512 (12)0.0308 (9)0.0353 (10)0.0024 (8)0.0033 (8)0.0044 (8)
C50.0464 (11)0.0281 (9)0.0367 (10)0.0034 (8)0.0066 (8)0.0034 (7)
C60.0365 (10)0.0287 (9)0.0277 (9)0.0014 (7)0.0025 (7)0.0018 (7)
C70.0418 (10)0.0293 (9)0.0314 (9)0.0012 (8)0.0043 (8)0.0059 (7)
C80.0375 (10)0.0323 (9)0.0286 (9)0.0007 (7)0.0057 (7)0.0000 (7)
C90.0512 (11)0.0318 (9)0.0282 (9)0.0047 (8)0.0088 (8)0.0029 (7)
C100.0484 (11)0.0326 (9)0.0320 (10)0.0011 (8)0.0062 (8)0.0037 (7)
C110.0416 (10)0.0390 (10)0.0259 (9)0.0014 (8)0.0082 (8)0.0004 (7)
C120.0544 (12)0.0397 (10)0.0296 (10)0.0069 (9)0.0049 (8)0.0040 (8)
C130.0463 (11)0.0512 (12)0.0262 (9)0.0042 (9)0.0002 (8)0.0015 (8)
C140.0375 (10)0.0428 (11)0.0286 (9)0.0056 (8)0.0089 (8)0.0043 (8)
C150.0446 (11)0.0348 (10)0.0338 (10)0.0030 (8)0.0069 (8)0.0005 (8)
C160.0425 (10)0.0423 (11)0.0255 (9)0.0026 (8)0.0020 (8)0.0016 (7)
C170.0590 (13)0.0438 (12)0.0484 (12)0.0063 (10)0.0148 (10)0.0112 (9)
Geometric parameters (Å, º) top
O1—C11.364 (2)C8—C91.502 (2)
O1—C91.444 (2)C9—H9A0.97
O2—C71.236 (2)C9—H9B0.97
O3—C31.351 (2)C10—C111.460 (2)
O3—H30.82C10—H100.93
O4—C141.364 (2)C11—C161.393 (3)
O4—C171.429 (2)C11—C121.400 (2)
C1—C21.383 (2)C12—C131.369 (3)
C1—C61.401 (2)C12—H120.93
C2—C31.386 (2)C13—C141.387 (3)
C2—H20.93C13—H130.93
C3—C41.395 (3)C14—C151.389 (3)
C4—C51.371 (3)C15—C161.385 (2)
C4—H40.93C15—H150.93
C5—C61.405 (2)C16—H160.93
C5—H50.93C17—H17A0.96
C6—C71.464 (2)C17—H17B0.96
C7—C81.482 (2)C17—H17C0.96
C8—C101.340 (2)
C1—O1—C9116.08 (13)O1—C9—H9B108.9
C3—O3—H3109.5C8—C9—H9B108.9
C14—O4—C17118.30 (15)H9A—C9—H9B107.7
O1—C1—C2116.48 (15)C8—C10—C11130.10 (17)
O1—C1—C6122.26 (15)C8—C10—H10115.0
C2—C1—C6121.21 (16)C11—C10—H10115.0
C1—C2—C3119.68 (16)C16—C11—C12117.16 (16)
C1—C2—H2120.2C16—C11—C10123.33 (16)
C3—C2—H2120.2C12—C11—C10119.45 (16)
O3—C3—C2116.57 (16)C13—C12—C11121.82 (17)
O3—C3—C4123.04 (16)C13—C12—H12119.1
C2—C3—C4120.38 (16)C11—C12—H12119.1
C5—C4—C3119.40 (16)C12—C13—C14119.98 (17)
C5—C4—H4120.3C12—C13—H13120.0
C3—C4—H4120.3C14—C13—H13120.0
C4—C5—C6121.77 (16)O4—C14—C13115.61 (16)
C4—C5—H5119.1O4—C14—C15124.56 (17)
C6—C5—H5119.1C13—C14—C15119.82 (16)
C1—C6—C5117.53 (15)C16—C15—C14119.42 (17)
C1—C6—C7120.44 (15)C16—C15—H15120.3
C5—C6—C7121.87 (15)C14—C15—H15120.3
O2—C7—C6121.69 (16)C15—C16—C11121.77 (17)
O2—C7—C8122.30 (16)C15—C16—H16119.1
C6—C7—C8116.01 (14)C11—C16—H16119.1
C10—C8—C7119.86 (16)O4—C17—H17A109.5
C10—C8—C9124.45 (16)O4—C17—H17B109.5
C7—C8—C9115.68 (14)H17A—C17—H17B109.5
O1—C9—C8113.30 (14)O4—C17—H17C109.5
O1—C9—H9A108.9H17A—C17—H17C109.5
C8—C9—H9A108.9H17B—C17—H17C109.5
C9—O1—C1—C2158.14 (16)O2—C7—C8—C9165.46 (18)
C9—O1—C1—C624.3 (2)C6—C7—C8—C915.2 (2)
O1—C1—C2—C3178.80 (16)C1—O1—C9—C846.1 (2)
C6—C1—C2—C31.2 (3)C10—C8—C9—O1138.66 (18)
C1—C2—C3—O3179.93 (17)C7—C8—C9—O141.4 (2)
C1—C2—C3—C40.3 (3)C7—C8—C10—C11175.48 (18)
O3—C3—C4—C5179.00 (18)C9—C8—C10—C114.5 (3)
C2—C3—C4—C51.4 (3)C8—C10—C11—C1631.5 (3)
C3—C4—C5—C61.0 (3)C8—C10—C11—C12151.4 (2)
O1—C1—C6—C5179.03 (16)C16—C11—C12—C131.9 (3)
C2—C1—C6—C51.6 (3)C10—C11—C12—C13179.19 (18)
O1—C1—C6—C73.4 (3)C11—C12—C13—C141.8 (3)
C2—C1—C6—C7173.97 (17)C17—O4—C14—C13168.63 (17)
C4—C5—C6—C10.5 (3)C17—O4—C14—C1510.9 (3)
C4—C5—C6—C7175.02 (17)C12—C13—C14—O4179.27 (17)
C1—C6—C7—O2171.95 (17)C12—C13—C14—C150.3 (3)
C5—C6—C7—O23.4 (3)O4—C14—C15—C16179.46 (17)
C1—C6—C7—C87.4 (2)C13—C14—C15—C161.0 (3)
C5—C6—C7—C8177.20 (16)C14—C15—C16—C110.9 (3)
O2—C7—C8—C1014.5 (3)C12—C11—C16—C150.5 (3)
C6—C7—C8—C10164.84 (17)C10—C11—C16—C15177.73 (17)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—H3···O2i0.821.942.686 (2)151
C10—H10···O20.932.472.826 (2)103
C13—H13···O4ii0.932.593.506 (3)168
C17—H17B···O3iii0.962.493.398 (2)158
Symmetry codes: (i) x, y+1/2, z1/2; (ii) x+2, y, z+2; (iii) x+1, y, z+1.
 

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