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The title compound, C19H14O4, crystallizes with two mol­ecules in the asymmetric unit. The di­hydro­pyran rings adopt a half-chair conformation or a conformation intermediate between a sofa and half-chair. The inversion-related type A and B mol­ecules and vice versa are linked by C—H...O hydrogen bonds, forming an infinite chain along the a axis. The molecular packing is stabilized by C—H...O interactions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803018075/fl6048sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803018075/fl6048Isup2.hkl
Contains datablock I

CCDC reference: 222906

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.065
  • wR factor = 0.167
  • Data-to-parameter ratio = 25.4

checkCIF/PLATON results

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Alert level A PLAT029_ALERT_3_A _diffrn_measured_fraction_theta_full Low ..... 0.92
Alert level C PLAT141_ALERT_4_C su on a - Axis Small or Missing (x 100000) ... 10 Ang.
1 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 0 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 1 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion

Comment top

Coumarin derivatives can undergo photocycloaddition with themselves (Song et al., 1971). Coumarin dyes are widely used in lasers owing to their tunability (Masilamani et al., 1986; Elnagdi et al., 1997). The coumarin ring system is also present in a number of natural products (Cisowski, 1983, 1984), which are found to possess antimicrobial (Zaha & Hazen, 2002), antioxidant (Wei et al., 1999; Sugioka et al., 1997), anticoagulation (Cole et al., 1988) and antiplatelet (Roma et al., 2003) activities. 4,7-Disubstituted coumarins give rise to interesting crystal structures in terms of their photochemical reactivity (Gnanaguru et al., 1985). The X-ray crystal structure analysis of the title compound, (I), was carried out as part of our studies on coumarin derivatives.

The title molecule, (I), consists of the coumarin moiety (ring A and B), two dihydropyran rings (C and D) and a benzene ring (E) fused together. There are two crystallographically independent molecules in the asymmetric unit. In both molecules, the bonds O1—C2 and O1—C6 are nearly equal in length, but slightly shorter than previously reported values (Krishna et al., 2003). The bond lengths C2O2, C2—C3, C3C4 and C5—C6, and the endocyclic angles of the pyrone ring (B) agree well with those reported in related stuctures (Ruggiero et al., 1989; Chinnakali et al., 1992). The coumarin moiety is planar except that atom C2 has deviations of −0.097 (2) and 0.040 (2) Å for molecules A and B, respectively. Atom O2 is displaced from the coumarin plane by −0.289 (1) and 0.136 (1) Å for molecules A and B, respectively. The dihedral angles between the aromatic ring (A) and the pyrone ring (B) are 3.2 (1) and 1.4 (1)° for molecules A and B, respectively. In both molecules, the dihedral angles between the dihydropyran rings (C and D) are 66.5 (1) and 64.8 (1)°, respectively. In both molecules, dihydropyran ring C adopts a conformation intermediate between a sofa and a half-chair, with asymmetric parameters (Nardelli, 1983) of ΔCS(C4A) = 0.059 (1) and ΔC2(C4A—C3A)= 0.063 (1) for molecule A, and ΔCS(C4B) = 0.065 (1) and ΔC2(C4B—C3B)= 0.061 (1) for molecule B. Dihydropyran ring D has a half-chair conformation in molecule A [ΔC2(C15A—C14A) = 0.015 (1)] and is intermediate between a sofa and a half-chair in molecule B [ΔCS(C15B) = 0.059 (1) and ΔC2(C15B—C14B) = 0.027 (1)].

Carbonyl atom O2 at (x, y, z) acts as a bifurcated acceptor from the H atoms on C16 and C7 of neighbouring molecules [at (2 − x, 1/2 + y, 1/2 − z) and (1 − x, 1/2 + y, 1/2 − z) for molecule A, and at (2 − x, −1/2 + y, 1/2 − z) and (1 − x, −1/2 + y, 1/2 − z) for molecule B]. Inversion-related A and B molecules and vice versa are linked by C—H···O interactions and form an infinite chain along the a axis (Fig. 2). The molecular packing is stabilized by C—H···O and weak C—H···π interactions (Table 2). In Table 2, Cg denotes the centroid of aromatic ring A.

Experimental top

To a refluxing solution of 3-(2-alloxybenzylidine)chroman-2,4-dione (0.31 g, 1 mmol) in 20 ml of nitromethane, lithium perchlorolate (0.11 g, 1 mmol) was added. After 12 h, work-up and flash-column chromatagraphy afforded the cycloadduct in 38% yield. The crystals were grown from a combination of methanol/chloroform by slow evaporation.

Refinement top

All H atoms were included in calculated positions and allowed to ride on their corresponding parent atoms.

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ZORTEP (Zsolnai, 1997) and PLATON (Spek, 1990); software used to prepare material for publication: SHELXL97 and PARST (Nardelli, 1995).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound, showing 35% probability displacement elliposid and the atom-numbering scheme.
[Figure 2] Fig. 2. The crystal packing of the molecule viewed down c axis,
6a,14a-cis-6,6a,7,14a-Tetrahydrochromeno[4',3':3,4]pyrano[3,2-c]coumarin top
Crystal data top
C19H14O4F(000) = 1280
Mr = 306.30Dx = 1.406 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 9616 reflections
a = 12.2252 (1) Åθ = 2.8–33.2°
b = 16.3351 (3) ŵ = 0.10 mm1
c = 15.3425 (3) ÅT = 293 K
β = 109.207 (1)°Block, colourless
V = 2893.35 (8) Å30.44 × 0.40 × 0.22 mm
Z = 8
Data collection top
Siemens SMART 1K CCD area-detector
diffractometer
6116 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.031
Graphite monochromatorθmax = 33.2°, θmin = 2.8°
ω scansh = 189
25479 measured reflectionsk = 2424
10531 independent 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)] = 0.066Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.167H-atom parameters constrained
S = 1.07 w = 1/[σ2(Fo2) + (0.0539P)2 + 0.8287P]
where P = (Fo2 + 2Fc2)/3
10531 reflections(Δ/σ)max < 0.001
415 parametersΔρmax = 0.28 e Å3
0 restraintsΔρmin = 0.22 e Å3
Crystal data top
C19H14O4V = 2893.35 (8) Å3
Mr = 306.30Z = 8
Monoclinic, P21/cMo Kα radiation
a = 12.2252 (1) ŵ = 0.10 mm1
b = 16.3351 (3) ÅT = 293 K
c = 15.3425 (3) Å0.44 × 0.40 × 0.22 mm
β = 109.207 (1)°
Data collection top
Siemens SMART 1K CCD area-detector
diffractometer
6116 reflections with I > 2σ(I)
25479 measured reflectionsRint = 0.031
10531 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0660 restraints
wR(F2) = 0.167H-atom parameters constrained
S = 1.07Δρmax = 0.28 e Å3
10531 reflectionsΔρmin = 0.22 e Å3
415 parameters
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
O1A0.81696 (10)0.52353 (7)0.40126 (9)0.0460 (3)
O2A0.68208 (11)0.60333 (8)0.42118 (10)0.0561 (3)
O3A0.59638 (10)0.32610 (7)0.33785 (9)0.0455 (3)
O4A0.25966 (10)0.43271 (8)0.26001 (9)0.0529 (3)
C2A0.70422 (14)0.53606 (10)0.39770 (11)0.0411 (4)
C3A0.62236 (13)0.46990 (9)0.36671 (10)0.0352 (3)
C4A0.66200 (13)0.39405 (9)0.35680 (11)0.0362 (3)
C5A0.78270 (13)0.37947 (10)0.36883 (10)0.0372 (3)
C6A0.85639 (14)0.44687 (10)0.38954 (11)0.0395 (3)
C7A0.97387 (15)0.43920 (12)0.40214 (12)0.0475 (4)
H7A1.02180.48490.41420.057*
C8A1.01744 (16)0.36306 (13)0.39639 (12)0.0514 (4)
H8A1.09630.35700.40640.062*
C9A0.94611 (16)0.29448 (13)0.37584 (12)0.0494 (4)
H9A0.97730.24320.37180.059*
C10A0.82897 (15)0.30248 (11)0.36138 (11)0.0432 (4)
H10A0.78100.25680.34670.052*
C11A0.47372 (14)0.33633 (10)0.31907 (13)0.0438 (4)
H11A0.44120.28510.33100.053*
H11B0.43740.34940.25430.053*
C12A0.44571 (14)0.40321 (10)0.37689 (11)0.0386 (3)
H12A0.48040.38870.44220.046*
C13A0.49776 (13)0.48470 (9)0.35993 (11)0.0356 (3)
H13A0.49730.52270.40930.043*
C14A0.42310 (13)0.52157 (9)0.26797 (11)0.0358 (3)
C15A0.31038 (14)0.49340 (10)0.22483 (12)0.0413 (4)
C16A0.31652 (15)0.41106 (11)0.35480 (12)0.0458 (4)
H16A0.28560.35950.36770.055*
H16B0.30060.45260.39420.055*
C17A0.24301 (16)0.52449 (13)0.13971 (13)0.0543 (5)
H17A0.16840.50460.11150.065*
C18A0.28592 (18)0.58455 (13)0.09692 (14)0.0582 (5)
H18A0.24060.60500.03990.070*
C19A0.39635 (18)0.61423 (12)0.13889 (14)0.0549 (5)
H19A0.42550.65510.11050.066*
C20A0.46349 (16)0.58301 (10)0.22317 (13)0.0461 (4)
H20A0.53780.60360.25090.055*
O1B0.66184 (10)0.16108 (8)0.08697 (9)0.0489 (3)
O2B0.79637 (11)0.07284 (7)0.08321 (9)0.0528 (3)
O3B0.89363 (10)0.35224 (7)0.14674 (8)0.0434 (3)
O4B1.22624 (11)0.23412 (9)0.22756 (10)0.0600 (4)
C2B0.77600 (14)0.14314 (10)0.09760 (11)0.0402 (3)
C3B0.86045 (13)0.20829 (9)0.12349 (10)0.0353 (3)
C4B0.82432 (13)0.28612 (9)0.12986 (10)0.0358 (3)
C5B0.70387 (14)0.30489 (10)0.11545 (10)0.0386 (3)
C6B0.62643 (15)0.23977 (11)0.09467 (11)0.0434 (4)
C7B0.50879 (16)0.25140 (14)0.07992 (13)0.0537 (5)
H7B0.45790.20730.06740.064*
C8B0.46998 (17)0.32957 (15)0.08439 (14)0.0607 (5)
H8B0.39150.33830.07370.073*
C9B0.54525 (18)0.39608 (14)0.10454 (14)0.0581 (5)
H9B0.51700.44860.10690.070*
C10B0.66212 (16)0.38382 (12)0.12105 (12)0.0483 (4)
H10B0.71300.42790.13590.058*
C11B1.01600 (14)0.33738 (10)0.16789 (12)0.0413 (4)
H11C1.04990.32480.23310.050*
H11D1.05260.38670.15570.050*
C12B1.04043 (14)0.26762 (10)0.11211 (11)0.0404 (3)
H12B1.00570.28080.04640.048*
C13B0.98440 (14)0.18897 (9)0.13188 (11)0.0371 (3)
H13B0.98340.14880.08420.045*
C14B1.05716 (14)0.15392 (9)0.22548 (11)0.0395 (3)
C15B1.17234 (15)0.17816 (11)0.26614 (13)0.0481 (4)
C16B1.16889 (16)0.25488 (12)0.13290 (14)0.0512 (4)
H16C1.18090.21140.09400.061*
H16D1.20270.30460.11830.061*
C17B1.23934 (19)0.14793 (14)0.35180 (16)0.0666 (6)
H17B1.31560.16530.37820.080*
C18B1.1934 (2)0.09256 (14)0.39755 (16)0.0705 (6)
H18B1.23860.07230.45470.085*
C19B1.0802 (2)0.06711 (12)0.35862 (15)0.0639 (6)
H19B1.04880.02970.38950.077*
C20B1.01356 (16)0.09726 (10)0.27363 (13)0.0492 (4)
H20B0.93750.07930.24780.059*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O1A0.0354 (6)0.0408 (6)0.0576 (7)0.0078 (5)0.0096 (5)0.0025 (5)
O2A0.0495 (7)0.0369 (6)0.0764 (9)0.0064 (5)0.0132 (6)0.0111 (6)
O3A0.0346 (6)0.0327 (6)0.0684 (8)0.0039 (4)0.0155 (5)0.0058 (5)
O4A0.0353 (6)0.0609 (8)0.0576 (8)0.0098 (6)0.0086 (5)0.0119 (6)
C2A0.0378 (8)0.0376 (8)0.0420 (8)0.0051 (7)0.0053 (7)0.0001 (7)
C3A0.0319 (7)0.0336 (7)0.0365 (7)0.0032 (6)0.0065 (6)0.0005 (6)
C4A0.0332 (7)0.0353 (7)0.0372 (8)0.0047 (6)0.0074 (6)0.0012 (6)
C5A0.0338 (8)0.0415 (8)0.0343 (7)0.0003 (6)0.0087 (6)0.0008 (6)
C6A0.0355 (8)0.0447 (9)0.0357 (8)0.0032 (6)0.0082 (6)0.0004 (7)
C7A0.0354 (8)0.0620 (11)0.0443 (9)0.0084 (8)0.0122 (7)0.0009 (8)
C8A0.0359 (9)0.0762 (13)0.0444 (9)0.0032 (9)0.0164 (7)0.0022 (9)
C9A0.0473 (10)0.0594 (11)0.0443 (9)0.0119 (9)0.0186 (8)0.0011 (8)
C10A0.0423 (9)0.0453 (9)0.0421 (9)0.0031 (7)0.0140 (7)0.0008 (7)
C11A0.0340 (8)0.0352 (8)0.0602 (11)0.0050 (6)0.0129 (7)0.0031 (7)
C12A0.0364 (8)0.0393 (8)0.0400 (8)0.0012 (6)0.0126 (6)0.0047 (7)
C13A0.0349 (8)0.0334 (7)0.0365 (7)0.0005 (6)0.0093 (6)0.0017 (6)
C14A0.0351 (7)0.0320 (7)0.0391 (8)0.0028 (6)0.0106 (6)0.0010 (6)
C15A0.0367 (8)0.0412 (8)0.0453 (9)0.0016 (7)0.0124 (7)0.0029 (7)
C16A0.0416 (9)0.0467 (9)0.0533 (10)0.0004 (7)0.0211 (8)0.0068 (8)
C17A0.0394 (9)0.0625 (12)0.0520 (10)0.0003 (8)0.0029 (8)0.0077 (9)
C18A0.0582 (12)0.0599 (12)0.0482 (10)0.0086 (10)0.0063 (9)0.0134 (9)
C19A0.0637 (12)0.0437 (10)0.0545 (11)0.0001 (9)0.0156 (9)0.0147 (8)
C20A0.0459 (9)0.0356 (8)0.0532 (10)0.0031 (7)0.0115 (8)0.0044 (7)
O1B0.0391 (6)0.0468 (7)0.0569 (7)0.0125 (5)0.0107 (5)0.0048 (6)
O2B0.0552 (8)0.0368 (6)0.0607 (8)0.0105 (6)0.0114 (6)0.0073 (6)
O3B0.0372 (6)0.0325 (5)0.0589 (7)0.0049 (5)0.0137 (5)0.0036 (5)
O4B0.0394 (7)0.0660 (9)0.0691 (9)0.0106 (6)0.0103 (6)0.0082 (7)
C2B0.0403 (8)0.0395 (8)0.0367 (8)0.0087 (7)0.0072 (6)0.0008 (6)
C3B0.0355 (8)0.0334 (7)0.0336 (7)0.0059 (6)0.0068 (6)0.0023 (6)
C4B0.0354 (8)0.0359 (7)0.0340 (7)0.0058 (6)0.0085 (6)0.0006 (6)
C5B0.0369 (8)0.0432 (8)0.0340 (7)0.0010 (7)0.0094 (6)0.0008 (6)
C6B0.0385 (8)0.0522 (10)0.0370 (8)0.0050 (7)0.0090 (7)0.0009 (7)
C7B0.0362 (9)0.0730 (13)0.0507 (10)0.0081 (9)0.0126 (8)0.0057 (9)
C8B0.0398 (10)0.0899 (16)0.0527 (11)0.0065 (10)0.0158 (8)0.0026 (11)
C9B0.0548 (12)0.0646 (13)0.0566 (11)0.0160 (10)0.0206 (9)0.0000 (10)
C10B0.0480 (10)0.0485 (10)0.0494 (10)0.0036 (8)0.0172 (8)0.0003 (8)
C11B0.0367 (8)0.0353 (8)0.0511 (9)0.0073 (6)0.0132 (7)0.0030 (7)
C12B0.0415 (9)0.0416 (8)0.0395 (8)0.0054 (7)0.0152 (7)0.0019 (7)
C13B0.0378 (8)0.0338 (7)0.0387 (8)0.0032 (6)0.0111 (6)0.0060 (6)
C14B0.0402 (8)0.0318 (7)0.0435 (8)0.0006 (6)0.0096 (7)0.0040 (6)
C15B0.0406 (9)0.0423 (9)0.0563 (10)0.0020 (7)0.0089 (8)0.0009 (8)
C16B0.0448 (10)0.0538 (11)0.0605 (11)0.0033 (8)0.0248 (9)0.0009 (9)
C17B0.0482 (11)0.0616 (13)0.0713 (14)0.0057 (9)0.0055 (10)0.0083 (11)
C18B0.0684 (14)0.0557 (12)0.0651 (13)0.0010 (10)0.0081 (11)0.0141 (10)
C19B0.0715 (14)0.0451 (11)0.0628 (13)0.0082 (10)0.0055 (10)0.0134 (9)
C20B0.0488 (10)0.0372 (8)0.0548 (10)0.0063 (7)0.0078 (8)0.0034 (8)
Geometric parameters (Å, º) top
O1A—C6A1.375 (2)O1B—C6B1.374 (2)
O1A—C2A1.377 (2)O1B—C2B1.382 (2)
O2A—C2A1.214 (2)O2B—C2B1.211 (2)
O3A—C4A1.344 (2)O3B—C4B1.344 (2)
O3A—C11A1.441 (2)O3B—C11B1.443 (2)
O4A—C15A1.371 (2)O4B—C15B1.370 (2)
O4A—C16A1.435 (2)O4B—C16B1.430 (2)
C2A—C3A1.443 (2)C2B—C3B1.444 (2)
C3A—C4A1.357 (2)C3B—C4B1.360 (2)
C3A—C13A1.512 (2)C3B—C13B1.511 (2)
C4A—C5A1.445 (2)C4B—C5B1.448 (2)
C5A—C6A1.392 (2)C5B—C6B1.390 (2)
C5A—C10A1.399 (2)C5B—C10B1.400 (2)
C6A—C7A1.390 (2)C6B—C7B1.393 (2)
C7A—C8A1.367 (3)C7B—C8B1.372 (3)
C7A—H7A0.9300C7B—H7B0.9300
C8A—C9A1.391 (3)C8B—C9B1.391 (3)
C8A—H8A0.9300C8B—H8B0.9300
C9A—C10A1.381 (2)C9B—C10B1.381 (3)
C9A—H9A0.9300C9B—H9B0.9300
C10A—H10A0.9300C10B—H10B0.9300
C11A—C12A1.516 (2)C11B—C12B1.513 (2)
C11A—H11A0.9700C11B—H11C0.9700
C11A—H11B0.9700C11B—H11D0.9700
C12A—C16A1.508 (2)C12B—C16B1.510 (2)
C12A—C13A1.534 (2)C12B—C13B1.532 (2)
C12A—H12A0.9800C12B—H12B0.9800
C13A—C14A1.529 (2)C13B—C14B1.530 (2)
C13A—H13A0.9800C13B—H13B0.9800
C14A—C20A1.395 (2)C14B—C20B1.395 (2)
C14A—C15A1.396 (2)C14B—C15B1.397 (2)
C15A—C17A1.391 (2)C15B—C17B1.391 (3)
C16A—H16A0.9700C16B—H16C0.9700
C16A—H16B0.9700C16B—H16D0.9700
C17A—C18A1.377 (3)C17B—C18B1.373 (3)
C17A—H17A0.9300C17B—H17B0.9300
C18A—C19A1.379 (3)C18B—C19B1.379 (3)
C18A—H18A0.9300C18B—H18B0.9300
C19A—C20A1.381 (3)C19B—C20B1.381 (3)
C19A—H19A0.9300C19B—H19B0.9300
C20A—H20A0.9300C20B—H20B0.9300
C6A—O1A—C2A121.3 (1)C6B—O1B—C2B121.5 (1)
C4A—O3A—C11A117.1 (1)C4B—O3B—C11B116.7 (1)
C15A—O4A—C16A116.5 (1)C15B—O4B—C16B116.9 (1)
O2A—C2A—O1A116.2 (1)O2B—C2B—O1B116.1 (1)
O2A—C2A—C3A125.3 (2)O2B—C2B—C3B125.3 (2)
O1A—C2A—C3A118.6 (1)O1B—C2B—C3B118.6 (1)
C4A—C3A—C2A119.1 (1)C4B—C3B—C2B119.3 (2)
C4A—C3A—C13A121.8 (1)C4B—C3B—C13B122.0 (1)
C2A—C3A—C13A118.5 (1)C2B—C3B—C13B118.4 (1)
O3A—C4A—C3A124.7 (1)O3B—C4B—C3B124.5 (1)
O3A—C4A—C5A113.8 (1)O3B—C4B—C5B113.8 (1)
C3A—C4A—C5A121.6 (1)C3B—C4B—C5B121.7 (1)
C6A—C5A—C10A118.8 (2)C6B—C5B—C10B119.0 (1)
C6A—C5A—C4A117.1 (2)C6B—C5B—C4B117.1 (2)
C10A—C5A—C4A124.1 (2)C10B—C5B—C4B124.0 (2)
O1A—C6A—C5A121.5 (1)O1B—C6B—C5B121.7 (2)
O1A—C6A—C7A117.0 (2)O1B—C6B—C7B116.8 (2)
C5A—C6A—C7A121.5 (2)C5B—C6B—C7B121.5 (2)
C8A—C7A—C6A118.7 (2)C8B—C7B—C6B118.3 (2)
C8A—C7A—H7A120.7C8B—C7B—H7B120.8
C6A—C7A—H7A120.7C6B—C7B—H7B120.8
C7A—C8A—C9A121.3 (2)C7B—C8B—C9B121.6 (2)
C7A—C8A—H8A119.4C7B—C8B—H8B119.2
C9A—C8A—H8A119.4C9B—C8B—H8B119.2
C10A—C9A—C8A120.0 (2)C10B—C9B—C8B119.7 (2)
C10A—C9A—H9A120.0C10B—C9B—H9B120.1
C8A—C9A—H9A120.0C8B—C9B—H9B120.1
C9A—C10A—C5A119.9 (2)C9B—C10B—C5B119.9 (2)
C9A—C10A—H10A120.1C9B—C10B—H10B120.0
C5A—C10A—H10A120.1C5B—C10B—H10B120.0
O3A—C11A—C12A112.8 (1)O3B—C11B—C12B112.5 (1)
O3A—C11A—H11A109.0O3B—C11B—H11C109.1
C12A—C11A—H11A109.0C12B—C11B—H11C109.1
O3A—C11A—H11B109.0O3B—C11B—H11D109.1
C12A—C11A—H11B109.0C12B—C11B—H11D109.1
H11A—C11A—H11B107.8H11C—C11B—H11D107.8
C16A—C12A—C11A110.6 (1)C16B—C12B—C11B111.7 (1)
C16A—C12A—C13A110.5 (1)C16B—C12B—C13B110.1 (1)
C11A—C12A—C13A109.9 (1)C11B—C12B—C13B109.6 (1)
C16A—C12A—H12A108.6C16B—C12B—H12B108.5
C11A—C12A—H12A108.6C11B—C12B—H12B108.5
C13A—C12A—H12A108.6C13B—C12B—H12B108.5
C3A—C13A—C14A114.1 (1)C3B—C13B—C14B114.5 (1)
C3A—C13A—C12A108.3 (1)C3B—C13B—C12B108.0 (1)
C14A—C13A—C12A110.1 (1)C14B—C13B—C12B109.9 (1)
C3A—C13A—H13A108.1C3B—C13B—H13B108.1
C14A—C13A—H13A108.1C14B—C13B—H13B108.1
C12A—C13A—H13A108.1C12B—C13B—H13B108.1
C20A—C14A—C15A117.2 (2)C20B—C14B—C15B117.2 (1)
C20A—C14A—C13A122.5 (1)C20B—C14B—C13B122.7 (2)
C15A—C14A—C13A120.3 (1)C15B—C14B—C13B120.2 (2)
O4A—C15A—C17A115.4 (2)O4B—C15B—C17B115.3 (2)
O4A—C15A—C14A123.8 (1)O4B—C15B—C14B123.6 (2)
C17A—C15A—C14A120.8 (2)C17B—C15B—C14B121.0 (2)
O4A—C16A—C12A111.8 (1)O4B—C16B—C12B112.1 (1)
O4A—C16A—H16A109.3O4B—C16B—H16C109.2
C12A—C16A—H16A109.3C12B—C16B—H16C109.2
O4A—C16A—H16B109.3O4B—C16B—H16D109.2
C12A—C16A—H16B109.3C12B—C16B—H16D109.2
H16A—C16A—H16B107.9H16C—C16B—H16D107.9
C18A—C17A—C15A120.5 (2)C18B—C17B—C15B120.3 (2)
C18A—C17A—H17A119.8C18B—C17B—H17B119.9
C15A—C17A—H17A119.8C15B—C17B—H17B119.9
C17A—C18A—C19A119.8 (2)C17B—C18B—C19B119.9 (2)
C17A—C18A—H18A120.1C17B—C18B—H18B120.1
C19A—C18A—H18A120.1C19B—C18B—H18B120.1
C18A—C19A—C20A119.8 (2)C20B—C19B—C18B119.8 (2)
C18A—C19A—H19A120.1C20B—C19B—H19B120.1
C20A—C19A—H19A120.1C18B—C19B—H19B120.1
C19A—C20A—C14A122.0 (2)C19B—C20B—C14B121.8 (2)
C19A—C20A—H20A119.0C19B—C20B—H20B119.1
C14A—C20A—H20A119.0C14B—C20B—H20B119.1
C6A—O1A—C2A—O2A170.3 (2)C6B—O1B—C2B—O2B175.1 (2)
C6A—O1A—C2A—C3A9.9 (2)C6B—O1B—C2B—C3B4.2 (2)
O2A—C2A—C3A—C4A169.4 (2)O2B—C2B—C3B—C4B174.4 (2)
O1A—C2A—C3A—C4A10.8 (2)O1B—C2B—C3B—C4B4.9 (2)
O2A—C2A—C3A—C13A1.7 (3)O2B—C2B—C3B—C13B1.3 (2)
O1A—C2A—C3A—C13A178.1 (1)O1B—C2B—C3B—C13B178.0 (1)
C11A—O3A—C4A—C3A5.6 (2)C11B—O3B—C4B—C3B6.1 (2)
C11A—O3A—C4A—C5A176.1 (1)C11B—O3B—C4B—C5B176.0 (1)
C2A—C3A—C4A—O3A172.8 (2)C2B—C3B—C4B—O3B175.0 (1)
C13A—C3A—C4A—O3A1.9 (2)C13B—C3B—C4B—O3B2.2 (2)
C2A—C3A—C4A—C5A5.4 (2)C2B—C3B—C4B—C5B2.9 (2)
C13A—C3A—C4A—C5A176.2 (1)C13B—C3B—C4B—C5B175.7 (1)
O3A—C4A—C5A—C6A179.4 (1)O3B—C4B—C5B—C6B178.0 (1)
C3A—C4A—C5A—C6A1.0 (2)C3B—C4B—C5B—C6B0.1 (2)
O3A—C4A—C5A—C10A0.3 (2)O3B—C4B—C5B—C10B1.9 (2)
C3A—C4A—C5A—C10A178.6 (2)C3B—C4B—C5B—C10B179.9 (2)
C2A—O1A—C6A—C5A3.4 (2)C2B—O1B—C6B—C5B1.4 (2)
C2A—O1A—C6A—C7A174.7 (1)C2B—O1B—C6B—C7B178.1 (2)
C10A—C5A—C6A—O1A177.5 (2)C10B—C5B—C6B—O1B179.1 (2)
C4A—C5A—C6A—O1A2.2 (2)C4B—C5B—C6B—O1B0.8 (2)
C10A—C5A—C6A—C7A0.5 (2)C10B—C5B—C6B—C7B0.4 (2)
C4A—C5A—C6A—C7A179.8 (2)C4B—C5B—C6B—C7B179.8 (2)
O1A—C6A—C7A—C8A176.2 (2)O1B—C6B—C7B—C8B178.1 (2)
C5A—C6A—C7A—C8A1.8 (3)C5B—C6B—C7B—C8B1.4 (3)
C6A—C7A—C8A—C9A1.8 (3)C6B—C7B—C8B—C9B1.0 (3)
C7A—C8A—C9A—C10A0.4 (3)C7B—C8B—C9B—C10B0.3 (3)
C8A—C9A—C10A—C5A1.0 (3)C8B—C9B—C10B—C5B1.4 (3)
C6A—C5A—C10A—C9A0.9 (2)C6B—C5B—C10B—C9B1.0 (3)
C4A—C5A—C10A—C9A178.8 (2)C4B—C5B—C10B—C9B178.8 (2)
C4A—O3A—C11A—C12A36.0 (2)C4B—O3B—C11B—C12B37.3 (2)
O3A—C11A—C12A—C16A179.8 (1)O3B—C11B—C12B—C16B178.1 (1)
O3A—C11A—C12A—C13A58.0 (2)O3B—C11B—C12B—C13B59.6 (2)
C4A—C3A—C13A—C14A102.5 (2)C4B—C3B—C13B—C14B102.4 (2)
C2A—C3A—C13A—C14A86.6 (2)C2B—C3B—C13B—C14B84.8 (2)
C4A—C3A—C13A—C12A20.5 (2)C4B—C3B—C13B—C12B20.4 (2)
C2A—C3A—C13A—C12A150.4 (1)C2B—C3B—C13B—C12B152.5 (1)
C16A—C12A—C13A—C3A170.2 (1)C16B—C12B—C13B—C3B171.9 (1)
C11A—C12A—C13A—C3A47.9 (2)C11B—C12B—C13B—C3B48.7 (2)
C16A—C12A—C13A—C14A44.8 (2)C16B—C12B—C13B—C14B46.3 (2)
C11A—C12A—C13A—C14A77.5 (2)C11B—C12B—C13B—C14B76.9 (2)
C3A—C13A—C14A—C20A40.9 (2)C3B—C13B—C14B—C20B39.9 (2)
C12A—C13A—C14A—C20A162.9 (2)C12B—C13B—C14B—C20B161.6 (2)
C3A—C13A—C14A—C15A138.4 (2)C3B—C13B—C14B—C15B140.3 (2)
C12A—C13A—C14A—C15A16.4 (2)C12B—C13B—C14B—C15B18.6 (2)
C16A—O4A—C15A—C17A167.9 (2)C16B—O4B—C15B—C17B168.5 (2)
C16A—O4A—C15A—C14A14.3 (2)C16B—O4B—C15B—C14B13.5 (3)
C20A—C14A—C15A—O4A179.2 (2)C20B—C14B—C15B—O4B179.0 (2)
C13A—C14A—C15A—O4A0.1 (2)C13B—C14B—C15B—O4B1.2 (3)
C20A—C14A—C15A—C17A1.4 (3)C20B—C14B—C15B—C17B1.2 (3)
C13A—C14A—C15A—C17A177.8 (2)C13B—C14B—C15B—C17B179.0 (2)
C15A—O4A—C16A—C12A44.6 (2)C15B—O4B—C16B—C12B43.4 (2)
C11A—C12A—C16A—O4A61.2 (2)C11B—C12B—C16B—O4B61.4 (2)
C13A—C12A—C16A—O4A60.7 (2)C13B—C12B—C16B—O4B60.6 (2)
O4A—C15A—C17A—C18A178.7 (2)O4B—C15B—C17B—C18B178.9 (2)
C14A—C15A—C17A—C18A0.9 (3)C14B—C15B—C17B—C18B0.8 (3)
C15A—C17A—C18A—C19A0.2 (3)C15B—C17B—C18B—C19B0.3 (4)
C17A—C18A—C19A—C20A0.6 (3)C17B—C18B—C19B—C20B0.2 (4)
C18A—C19A—C20A—C14A0.1 (3)C18B—C19B—C20B—C14B0.6 (3)
C15A—C14A—C20A—C19A1.1 (3)C15B—C14B—C20B—C19B1.1 (3)
C13A—C14A—C20A—C19A178.2 (2)C13B—C14B—C20B—C19B179.2 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C20B—H20B···O2B0.932.553.262 (2)134
C7B—H7B···O2Ai0.932.463.357 (2)163
C16A—H16B···O2Bii0.972.383.265 (2)152
C16B—H16C···O2Aiii0.972.503.336 (2)145
Symmetry codes: (i) x+1, y1/2, z+1/2; (ii) x+1, y+1/2, z+1/2; (iii) x+2, y1/2, z+1/2.

Experimental details

Crystal data
Chemical formulaC19H14O4
Mr306.30
Crystal system, space groupMonoclinic, P21/c
Temperature (K)293
a, b, c (Å)12.2252 (1), 16.3351 (3), 15.3425 (3)
β (°) 109.207 (1)
V3)2893.35 (8)
Z8
Radiation typeMo Kα
µ (mm1)0.10
Crystal size (mm)0.44 × 0.40 × 0.22
Data collection
DiffractometerSiemens SMART 1K CCD area-detector
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
25479, 10531, 6116
Rint0.031
(sin θ/λ)max1)0.770
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.066, 0.167, 1.07
No. of reflections10531
No. of parameters415
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.28, 0.22

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ZORTEP (Zsolnai, 1997) and PLATON (Spek, 1990), SHELXL97 and PARST (Nardelli, 1995).

Selected geometric parameters (Å, º) top
O1A—C6A1.375 (2)O1B—C6B1.374 (2)
O1A—C2A1.377 (2)O1B—C2B1.382 (2)
O2A—C2A1.214 (2)O2B—C2B1.211 (2)
O3A—C4A1.344 (2)O3B—C4B1.344 (2)
O3A—C11A1.441 (2)O3B—C11B1.443 (2)
O4A—C15A1.371 (2)O4B—C15B1.370 (2)
O4A—C16A1.435 (2)O4B—C16B1.430 (2)
C2A—C3A1.443 (2)C2B—C3B1.444 (2)
C3A—C4A1.357 (2)C3B—C4B1.360 (2)
C3A—C13A1.512 (2)C3B—C13B1.511 (2)
C4A—C5A1.445 (2)C4B—C5B1.448 (2)
C5A—C6A1.392 (2)C5B—C6B1.390 (2)
C11A—C12A1.516 (2)C11B—C12B1.513 (2)
C12A—C16A1.508 (2)C12B—C16B1.510 (2)
C12A—C13A1.534 (2)C12B—C13B1.532 (2)
C13A—C14A1.529 (2)C13B—C14B1.530 (2)
C6A—O1A—C2A121.3 (1)O4A—C15A—C14A123.8 (1)
C4A—O3A—C11A117.1 (1)C6B—O1B—C2B121.5 (1)
C15A—O4A—C16A116.5 (1)C4B—O3B—C11B116.7 (1)
O2A—C2A—O1A116.2 (1)C15B—O4B—C16B116.9 (1)
O2A—C2A—C3A125.3 (2)O1B—C2B—C3B118.6 (1)
O1A—C2A—C3A118.6 (1)C4B—C3B—C2B119.3 (2)
C4A—C3A—C2A119.1 (1)C4B—C3B—C13B122.0 (1)
C4A—C3A—C13A121.8 (1)O3B—C4B—C3B124.5 (1)
O3A—C4A—C3A124.7 (1)C3B—C4B—C5B121.7 (1)
C3A—C4A—C5A121.6 (1)C6B—C5B—C4B117.1 (2)
C6A—C5A—C4A117.1 (2)O1B—C6B—C5B121.7 (2)
O1A—C6A—C5A121.5 (1)O3B—C11B—C12B112.5 (1)
O3A—C11A—C12A112.8 (1)O4B—C15B—C14B123.6 (2)
C16A—C12A—C13A110.5 (1)O4B—C16B—C12B112.1 (1)
C13A—C3A—C4A—C5A176.2 (1)C13B—C3B—C4B—C5B175.7 (1)
C10A—C5A—C6A—O1A177.5 (2)C10B—C5B—C6B—O1B179.1 (2)
C20A—C14A—C15A—O4A179.2 (2)C20B—C14B—C15B—O4B179.0 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C20B—H20B···O2B0.932.553.262 (2)134
C7B—H7B···O2Ai0.932.463.357 (2)163
C16A—H16B···O2Bii0.972.383.265 (2)152
C16B—H16C···O2Aiii0.972.503.336 (2)145
Symmetry codes: (i) x+1, y1/2, z+1/2; (ii) x+1, y+1/2, z+1/2; (iii) x+2, y1/2, z+1/2.
 

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