Buy article online - an online subscription or single-article purchase is required to access this article.
share
share
Issue contentsclose
Statistics
close
Download citation
closeDownload citation
Format BIBTeX
EndNote
RefMan
Refer
Medline
CIF
SGML
Text
Plain Text
Download PDF of article
Download PDF of articleclose
Acta Cryst. (2012). C68, o413-o416
https://doi.org/10.1107/S010827011203805X
Download PDF of article
Download PDF of articleclose
Download citation
closeDownload citation
Format BIBTeX
EndNote
RefMan
Refer
Medline
CIF
SGML
Text
Plain Text
Statistics
close
Issue contentsclose
share
link to html

An irreversible phase transition in 1-n-butyl­indeno­[2,1-c]pyran-3,9-dione

A. S. Batsanov, J. A. K. Howard, N. Wu, Z. Yang and T. B. Marder
At ambient temperature, the title compound, C16H14O3, is triclinic, with the n-butyl side chain disordered in an out-of-plane orientation. On cooling below 240 K, it converts into a different triclinic phase with an ordered planar conformation and denser packing, which is retained on warming to room temperature. The transition (occasionally) proceeds from single crystal to single crystal.
Read articleSimilar articles

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S010827011203805X/em3055sup1.cif
Contains datablocks global, aI, bI, bIRT

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S010827011203805X/em3055aIsup2.hkl
Contains datablock aI

mol

MDL mol file https://doi.org/10.1107/S010827011203805X/em3055aIsup5.mol
Supplementary material

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S010827011203805X/em3055bIsup3.hkl
Contains datablock bI

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S010827011203805X/em3055bIRTsup4.hkl
Contains datablock bIRT

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S010827011203805X/em3055aIsup6.cml
Supplementary material

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S010827011203805X/em3055bIsup7.cml
Supplementary material

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S010827011203805X/em3055bIRTsup8.cml
Supplementary material

CCDC references: 852796; 906585; 906586; 906587

Comment top

In recent decades, crystal-to-crystal transformations, both physical and chemical, of organic and organometallic compounds have moved from being a crystallographic curiosity (Morawetz et al., 1963) to a focus of intense theoretical and applied interest (Dunitz, 1995; Gavezzotti & Filippini, 1995; Braga & Grepioni, 2005; Garcia-Garibay, 2007). Important aspects of the mechanism are still in dispute (Mnyukh, 2001; Herbstein, 2006; Merz et al., 2009), hence the significance of closely investigating new examples of these transformations. The titl compound, (I), which was obtained during our studies of palladium(II)-catalysed electrophilic cyclization of electron-deficient enynes (Wu et al., 2012), presents such an example.

Crystals of the α-polymorph of (I) were grown at room temperature by diffusion of n-hexane into an Et2O solution of (I). The structure is triclinic. The indeno[2,1-c]pyran-3,9-dione (ipd) system is planar and the n-butyl side-chain is disordered between two alternative conformations, viz. all-trans (A) and trans–gauche (B), with occupancies of 0.720 (4) and 0.280 (4), respectively. For the major conformation, atoms C12, C13, C14A, C15A and C16A are practically coplanar; their mean plane is inclined to the ipd plane by 60.7° (Fig. 1). For the minor conformation, the mean plane formed by atoms C12, C13, C14B and C15B is practically perpendicular to the ipd plane (interplanar angle = 89.0°), while the plane formed by atoms C14B, C15B and C16B is inclined to the latter by 31.6°. However, the mean vector of the C12–C16 chain has a similar direction in both cases, which differ by 6.6° and are inclined to the ipd plane by 26.3° for the major conformation and by 22.7° for the minor conformation.

The phase transition occurs on cooling below ca 240 K. It usually results in fracturing of the crystal, and always in its violent swinging on the mount, even when glued apparently rigidly with epoxy resin. On one occasion, after slow cooling (at a rate of 10 K h-1 near the transition) with periodic annealing, a fragment of a fractured crystal which remained on the mount was found to be a single crystal of X-ray quality of the new β-polymorph, also triclinic. This crystal was cooled to 120 K and a full data set was collected. The same crystal was then warmed to room temperature without any further phase transformation being observed, and a second data set was collected at 293 K. The structures of β-(I) determined at 120 and 293 K are essentially identical. The side-chain is ordered in an all-trans conformation, in this case practically coplanar with the ipd system (Fig. 1). At room temperature, β-(I) has a packing coefficient [calculated according to Gavezzotti (1983)] of 0.645, compared with a value of 0.615 for polymorph α-(I), and a correspondingly higher density (1.337 versus 1.276 Mg m-3). The thermal expansion coefficient of β-(I), 1.05 (3) × 10-4, is of the usual order of magnitude (Hofmann, 2002).

The crystal packing of polymorphs α-(I) and β-(I) is compared in Figs. 2 and 3. In both structures, molecules related via the a–b translation are practically coplanar, entirely for β-(I) or just as far as the ipd system is concerned in α-(I). In β-(I), the resulting planar ribbons form a slightly puckered layer (Fig. 3), whereas in α-(I) two adjacent ribbons are coplanar, but the next pair is shifted relative to them along the stacking direction. In both polymorphs, aromatic and aliphatic systems are segregated, which gives some leeway for the conformational realignment of the side-chains. However, the phase transition cannot be interpreted purely in terms of side-chains moving between stationary aromatic stacks, as there is also a very substantial shear between the aromatic systems. In fact, the layered appearance of the structures is somewhat deceptive. Although the mean interlayer separations are rather short [3.32 Å in α-(I) and 3.30 Å in β-(I) at 120 K], in neither structure is it possible to distinguish any meaningful stacks; only some fringe overlap between the aromatic systems of neighbouring layers is observed.

The absence of any rational relation between the unit cells of the two polymorphs, as well as the large intermolecular shifts required, suggest that the phase transition may be reconstructive (Mnyukh, 2001) rather than topotactic (Morawetz et al., 1963) and proceed through the usual process of nucleation and growth (Herbstein, 2006).

The crystal data of polymorph β-(I) at 120 K are reported without comment by Wu et al. (2012) [deposited in the Cambridge Structural Database (Allen, 2002) as deposition number CCDC-852796].

Related literature top

For related literature, see: Allen (2002); Braga & Grepioni (2005); Dunitz (1995); Garcia-Garibay (2007); Gavezzotti (1983); Gavezzotti & Filippini (1995); Herbstein (2006); Hofmann (2002); Merz et al. (2009); Mnyukh (2001); Morawetz et al. (1963); Wu et al. (2012).

Experimental top

The synthesis of (I) is described by Wu et al. (2012). o-EtO2CC═CC6H4C(═O)C≡CBu-n (0.15 mmol) was added to a solution of Pd(OAc)2 (10 mol%) and LiCl (4 equivalents) in acetic acid (3 ml). The mixture was stirred at 333 K in air until all the enyne was consumed (as monitored by gas chromatographic mass spectroscopy, GC–MS), then cooled and the solvent removed in vacuo. The residue was purified by flash chromatography to give (I). X-ray quality crystals of polymorph α-(I) were grown by solvent diffusion: a diethyl ether solution of (I) was placed in an open 10 ml vial within a closed 50 ml vial containing n-hexane.

Refinement top

Methyl groups were refined as rigid bodies rotating around the C—C bonds, with C—H = 0.98 Å. All other H atoms were treated as riding in idealized positions, with Csp2—H = 0.93 and Csp3—H = 0.97 Å at 293 K, and 0.95 and 0.99 Å, respectively, at 120 K. The Uiso(H) values for the methyl H atoms in β-(I) were refined, while in α-(I) they were constrained to 1.5Ueq(C), or 1.2Ueq(C) for non-methyl H atoms.

Structure description top

In recent decades, crystal-to-crystal transformations, both physical and chemical, of organic and organometallic compounds have moved from being a crystallographic curiosity (Morawetz et al., 1963) to a focus of intense theoretical and applied interest (Dunitz, 1995; Gavezzotti & Filippini, 1995; Braga & Grepioni, 2005; Garcia-Garibay, 2007). Important aspects of the mechanism are still in dispute (Mnyukh, 2001; Herbstein, 2006; Merz et al., 2009), hence the significance of closely investigating new examples of these transformations. The titl compound, (I), which was obtained during our studies of palladium(II)-catalysed electrophilic cyclization of electron-deficient enynes (Wu et al., 2012), presents such an example.

Crystals of the α-polymorph of (I) were grown at room temperature by diffusion of n-hexane into an Et2O solution of (I). The structure is triclinic. The indeno[2,1-c]pyran-3,9-dione (ipd) system is planar and the n-butyl side-chain is disordered between two alternative conformations, viz. all-trans (A) and trans–gauche (B), with occupancies of 0.720 (4) and 0.280 (4), respectively. For the major conformation, atoms C12, C13, C14A, C15A and C16A are practically coplanar; their mean plane is inclined to the ipd plane by 60.7° (Fig. 1). For the minor conformation, the mean plane formed by atoms C12, C13, C14B and C15B is practically perpendicular to the ipd plane (interplanar angle = 89.0°), while the plane formed by atoms C14B, C15B and C16B is inclined to the latter by 31.6°. However, the mean vector of the C12–C16 chain has a similar direction in both cases, which differ by 6.6° and are inclined to the ipd plane by 26.3° for the major conformation and by 22.7° for the minor conformation.

The phase transition occurs on cooling below ca 240 K. It usually results in fracturing of the crystal, and always in its violent swinging on the mount, even when glued apparently rigidly with epoxy resin. On one occasion, after slow cooling (at a rate of 10 K h-1 near the transition) with periodic annealing, a fragment of a fractured crystal which remained on the mount was found to be a single crystal of X-ray quality of the new β-polymorph, also triclinic. This crystal was cooled to 120 K and a full data set was collected. The same crystal was then warmed to room temperature without any further phase transformation being observed, and a second data set was collected at 293 K. The structures of β-(I) determined at 120 and 293 K are essentially identical. The side-chain is ordered in an all-trans conformation, in this case practically coplanar with the ipd system (Fig. 1). At room temperature, β-(I) has a packing coefficient [calculated according to Gavezzotti (1983)] of 0.645, compared with a value of 0.615 for polymorph α-(I), and a correspondingly higher density (1.337 versus 1.276 Mg m-3). The thermal expansion coefficient of β-(I), 1.05 (3) × 10-4, is of the usual order of magnitude (Hofmann, 2002).

The crystal packing of polymorphs α-(I) and β-(I) is compared in Figs. 2 and 3. In both structures, molecules related via the a–b translation are practically coplanar, entirely for β-(I) or just as far as the ipd system is concerned in α-(I). In β-(I), the resulting planar ribbons form a slightly puckered layer (Fig. 3), whereas in α-(I) two adjacent ribbons are coplanar, but the next pair is shifted relative to them along the stacking direction. In both polymorphs, aromatic and aliphatic systems are segregated, which gives some leeway for the conformational realignment of the side-chains. However, the phase transition cannot be interpreted purely in terms of side-chains moving between stationary aromatic stacks, as there is also a very substantial shear between the aromatic systems. In fact, the layered appearance of the structures is somewhat deceptive. Although the mean interlayer separations are rather short [3.32 Å in α-(I) and 3.30 Å in β-(I) at 120 K], in neither structure is it possible to distinguish any meaningful stacks; only some fringe overlap between the aromatic systems of neighbouring layers is observed.

The absence of any rational relation between the unit cells of the two polymorphs, as well as the large intermolecular shifts required, suggest that the phase transition may be reconstructive (Mnyukh, 2001) rather than topotactic (Morawetz et al., 1963) and proceed through the usual process of nucleation and growth (Herbstein, 2006).

The crystal data of polymorph β-(I) at 120 K are reported without comment by Wu et al. (2012) [deposited in the Cambridge Structural Database (Allen, 2002) as deposition number CCDC-852796].

For related literature, see: Allen (2002); Braga & Grepioni (2005); Dunitz (1995); Garcia-Garibay (2007); Gavezzotti (1983); Gavezzotti & Filippini (1995); Herbstein (2006); Hofmann (2002); Merz et al. (2009); Mnyukh (2001); Morawetz et al. (1963); Wu et al. (2012).

Computing details top

Data collection: SMART (Bruker, 2001) for aI, bI; SMART (Bruker, 2003) for bIRT. For all compounds, cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I) in (a) the α-polymorph at 293 K (dashed outlines indicate the minor disordered component?) and (b) the β-polymorph at 120 K. Displacement ellipsoids are drawn at the 50% probability level.
[Figure 2] Fig. 2. The molecular layers in (a) α-(I) (disorder omitted) and (b) β-(I).
[Figure 3] Fig. 3. The crystal packing of (a) α-(I) and (b) β-(I), viewed along the direction of the a–b translation [Revised text OK?] (indicated by the arrows in Fig. 2). Dashed boxes enclose the layers shown in Fig. 2.
(aI) 1-n-Butylindeno[2,1-c]pyran-3,9-dione top
Crystal data top
C16H14O3F(000) = 268
Mr = 254.27Dx = 1.276 Mg m−3
Triclinic, P1Melting point: 373.7(5) K
a = 4.6539 (6) ÅMo Kα radiation, λ = 0.71073 Å
b = 10.1800 (12) ÅCell parameters from 1209 reflections
c = 14.3718 (17) Åθ = 2.4–21.9°
α = 82.481 (5)°µ = 0.09 mm−1
β = 88.127 (7)°T = 293 K
γ = 78.604 (6)°Plate, colourless
V = 661.71 (14) Å30.22 × 0.18 × 0.06 mm
Z = 2
Data collection top
Bruker SMART CCD 6000 area-detector
diffractometer		1137 reflections with I > 2σ(I)
Radiation source: sealed X-ray tubeRint = 0.063
Graphite monochromatorθmax = 25.0°, θmin = 1.4°
Detector resolution: 5.6 pixels mm-1h = −5→5
ω scansk = −12→12
5329 measured reflectionsl = −16→17
2336 independent 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)] = 0.041Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.110H-atom parameters constrained
S = 0.84 w = 1/[σ2(Fo2) + (0.0525P)2]
where P = (Fo2 + 2Fc2)/3
2336 reflections(Δ/σ)max < 0.001
185 parametersΔρmax = 0.10 e Å−3
15 restraintsΔρmin = −0.14 e Å−3
Crystal data top
C16H14O3γ = 78.604 (6)°
Mr = 254.27V = 661.71 (14) Å3
Triclinic, P1Z = 2
a = 4.6539 (6) ÅMo Kα radiation
b = 10.1800 (12) ŵ = 0.09 mm−1
c = 14.3718 (17) ÅT = 293 K
α = 82.481 (5)°0.22 × 0.18 × 0.06 mm
β = 88.127 (7)°
Data collection top
Bruker SMART CCD 6000 area-detector
diffractometer		1137 reflections with I > 2σ(I)
5329 measured reflectionsRint = 0.063
2336 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.04115 restraints
wR(F2) = 0.110H-atom parameters constrained
S = 0.84Δρmax = 0.10 e Å−3
2336 reflectionsΔρmin = −0.14 e Å−3
185 parameters
Special details top

Experimental. The data collection nominally covered a full sphere of reciprocal space by a combination of 3 sets of ω scans each set at different φ angles and each scan (20 s exposure) covering -0.3° in ω. The crystal-to-detector distance was 4.83 cm. Phase transition occurs on cooling below 240 K.

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. Methyl groups were refined as rigid bodies rotating around C—C bonds. Other H atoms: riding in idealized positions. The C14H2C15H2C16H3 chain is disordered between two conformations, A and B, with occupancies refined to 0.719 (4) and 0.281 (4), respectively.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
O10.3523 (3)0.63740 (14)0.18082 (11)0.0659 (4)
O20.0149 (4)0.66916 (15)0.07167 (11)0.0808 (5)
O31.0635 (4)0.33233 (18)0.32844 (13)0.0944 (6)
C10.2122 (5)0.5888 (2)0.11157 (16)0.0613 (6)
C20.3168 (4)0.4515 (2)0.09622 (15)0.0605 (6)
H20.23330.41500.05020.073*
C30.5361 (4)0.3755 (2)0.14912 (15)0.0553 (6)
C40.6816 (5)0.2336 (2)0.15088 (16)0.0614 (6)
C50.6375 (6)0.1373 (2)0.09593 (19)0.0799 (7)
H50.49820.15800.04850.096*
C60.8076 (7)0.0090 (3)0.1137 (2)0.0988 (9)
H60.7813−0.05740.07790.119*
C71.0139 (7)−0.0220 (3)0.1830 (3)0.1012 (10)
H71.1254−0.10900.19300.121*
C81.0608 (6)0.0730 (3)0.2379 (2)0.0909 (8)
H81.20000.05100.28530.109*
C90.8918 (5)0.2016 (2)0.22028 (17)0.0677 (6)
C100.8990 (5)0.3235 (2)0.26654 (18)0.0681 (6)
C110.6686 (4)0.4301 (2)0.21968 (15)0.0552 (6)
C120.5754 (4)0.5593 (2)0.23414 (16)0.0598 (6)
C130.6839 (5)0.6342 (2)0.30300 (17)0.0765 (7)
H1330.67840.72720.27620.092*0.281 (4)
H1340.88470.59310.32000.092*0.281 (4)
H1310.76520.70700.26840.092*0.719 (4)
H1320.84330.57350.33760.092*0.719 (4)
C14A0.4626 (7)0.6900 (4)0.3742 (2)0.0757 (12)0.719 (4)
H1410.39190.61720.41270.091*0.719 (4)
H1420.29630.74660.34050.091*0.719 (4)
C15A0.5944 (8)0.7680 (6)0.4391 (3)0.0920 (15)0.719 (4)
H1510.75710.70750.47210.110*0.719 (4)
H1520.67050.84040.40200.110*0.719 (4)
C16A0.3720 (10)0.8233 (5)0.5098 (3)0.1216 (19)0.719 (4)
H1610.21420.89160.48230.182*0.719 (4)
H1620.46320.85850.55760.182*0.719 (4)
H1630.29610.74590.53750.182*0.719 (4)
C14B0.501 (2)0.6185 (11)0.3917 (4)0.0757 (12)0.281 (4)
H1430.49110.52480.41240.091*0.281 (4)
H1440.30450.66560.37360.091*0.281 (4)
C15B0.570 (3)0.6772 (10)0.4781 (7)0.0920 (15)0.281 (4)
H1530.42970.65670.52650.110*0.281 (4)
H1540.76450.63540.50130.110*0.281 (4)
C16B0.537 (4)0.8293 (11)0.4678 (15)0.147 (7)*0.281 (4)
H1640.69070.85600.42790.220*0.281 (4)
H1650.55030.85760.52850.220*0.281 (4)
H1660.35050.87080.44070.220*0.281 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0630 (9)0.0575 (9)0.0773 (11)−0.0027 (8)−0.0093 (8)−0.0207 (8)
O20.0874 (11)0.0648 (11)0.0820 (12)0.0083 (9)−0.0221 (10)−0.0095 (9)
O30.0820 (12)0.1039 (13)0.0927 (14)−0.0030 (10)−0.0290 (11)−0.0117 (11)
C10.0664 (15)0.0596 (15)0.0572 (15)−0.0072 (13)−0.0026 (12)−0.0116 (12)
C20.0702 (14)0.0562 (14)0.0561 (14)−0.0095 (12)−0.0045 (12)−0.0138 (12)
C30.0576 (13)0.0526 (13)0.0555 (14)−0.0098 (11)0.0046 (12)−0.0085 (11)
C40.0665 (15)0.0519 (14)0.0650 (16)−0.0088 (12)0.0083 (13)−0.0106 (12)
C50.0925 (18)0.0610 (16)0.0875 (19)−0.0121 (14)0.0057 (15)−0.0202 (14)
C60.111 (2)0.0602 (18)0.125 (3)−0.0116 (17)0.022 (2)−0.0265 (17)
C70.102 (2)0.0570 (18)0.134 (3)0.0024 (16)0.017 (2)−0.0070 (19)
C80.0825 (18)0.0688 (18)0.108 (2)0.0075 (15)−0.0015 (16)0.0048 (16)
C90.0661 (14)0.0552 (15)0.0766 (17)−0.0044 (12)0.0069 (13)−0.0029 (13)
C100.0596 (15)0.0760 (16)0.0660 (17)−0.0092 (13)−0.0048 (13)−0.0039 (14)
C110.0526 (12)0.0551 (14)0.0573 (14)−0.0069 (11)−0.0002 (11)−0.0111 (11)
C120.0497 (12)0.0667 (15)0.0656 (16)−0.0122 (12)−0.0019 (12)−0.0162 (13)
C130.0616 (14)0.0807 (16)0.0917 (19)−0.0108 (13)−0.0077 (14)−0.0307 (15)
C14A0.0694 (19)0.081 (3)0.077 (2)0.001 (2)−0.0139 (17)−0.035 (2)
C15A0.081 (2)0.126 (4)0.082 (3)−0.030 (3)−0.005 (2)−0.042 (3)
C16A0.109 (3)0.180 (5)0.097 (3)−0.047 (3)0.015 (3)−0.070 (3)
C14B0.0694 (19)0.081 (3)0.077 (2)0.001 (2)−0.0139 (17)−0.035 (2)
C15B0.081 (2)0.126 (4)0.082 (3)−0.030 (3)−0.005 (2)−0.042 (3)
Geometric parameters (Å, º) top
O1—C121.365 (2)C13—C14B1.518 (4)
O1—C11.400 (2)C13—H1330.9699
O2—C11.206 (2)C13—H1340.9703
O3—C101.216 (3)C13—H1310.9699
C1—C21.430 (3)C13—H1320.9703
C2—C31.343 (3)C14A—C15A1.517 (3)
C2—H20.9301C14A—H1410.9700
C3—C111.429 (3)C14A—H1420.9701
C3—C41.467 (3)C15A—C16A1.508 (4)
C4—C91.382 (3)C15A—H1510.9702
C4—C51.386 (3)C15A—H1520.9700
C5—C61.383 (3)C16A—H1610.9613
C5—H50.9302C16A—H1620.9612
C6—C71.369 (4)C16A—H1630.9608
C6—H60.9300C14B—C15B1.517 (4)
C7—C81.379 (4)C14B—H1430.9701
C7—H70.9301C14B—H1440.9701
C8—C91.384 (3)C15B—C16B1.514 (4)
C8—H80.9302C15B—H1530.9702
C9—C101.489 (3)C15B—H1540.9701
C10—C111.475 (3)C16B—H1640.9600
C11—C121.342 (3)C16B—H1650.9600
C12—C131.483 (3)C16B—H1660.9600
C13—C14A1.510 (3)
C12—O1—C1123.03 (17)C12—C13—H134110.2
O2—C1—O1115.3 (2)C14A—C13—H134122.0
O2—C1—C2127.6 (2)C14B—C13—H134106.6
O1—C1—C2117.1 (2)H133—C13—H134108.5
C3—C2—C1119.4 (2)C12—C13—H131108.1
C3—C2—H2120.3C14A—C13—H131109.7
C1—C2—H2120.3C12—C13—H132108.1
C2—C3—C11121.07 (19)C14A—C13—H132107.3
C2—C3—C4131.5 (2)H131—C13—H132107.3
C11—C3—C4107.45 (19)C13—C14A—C15A111.6 (3)
C9—C4—C5120.5 (2)C13—C14A—H141110.4
C9—C4—C3109.2 (2)C15A—C14A—H141107.7
C5—C4—C3130.3 (2)C13—C14A—H142108.2
C6—C5—C4117.8 (3)C15A—C14A—H142111.2
C6—C5—H5120.9H141—C14A—H142107.7
C4—C5—H5121.2C13—C14A—H144114.7
C7—C6—C5121.3 (3)C16A—C15A—C14A111.3 (3)
C7—C6—H6119.4C16A—C15A—H151109.0
C5—C6—H6119.4C14A—C15A—H151108.6
C6—C7—C8121.5 (3)C16A—C15A—H152110.6
C6—C7—H7119.2C14A—C15A—H152109.3
C8—C7—H7119.3H151—C15A—H152108.0
C7—C8—C9117.5 (3)C15B—C14B—C13120.1 (8)
C7—C8—H8121.1C15B—C14B—H143106.2
C9—C8—H8121.4C13—C14B—H143112.3
C4—C9—C8121.4 (2)C15B—C14B—H144105.3
C4—C9—C10109.5 (2)C13—C14B—H144104.7
C8—C9—C10129.1 (2)H143—C14B—H144107.5
O3—C10—C11128.1 (2)C16B—C15B—C14B116.0 (12)
O3—C10—C9126.9 (2)C16B—C15B—H153104.8
C11—C10—C9105.0 (2)C14B—C15B—H153107.4
C12—C11—C3120.3 (2)C16B—C15B—H154109.4
C12—C11—C10130.9 (2)C14B—C15B—H154111.0
C3—C11—C10108.85 (19)H153—C15B—H154107.7
C11—C12—O1119.1 (2)C15B—C16B—H161108.5
C11—C12—C13128.4 (2)C15B—C16B—H164109.5
O1—C12—C13112.44 (19)C15B—C16B—H165109.5
C12—C13—C14A116.1 (2)H164—C16B—H165109.5
C12—C13—C14B107.2 (4)C15B—C16B—H166109.5
C12—C13—H133110.1H164—C16B—H166109.5
C14A—C13—H13386.7H165—C16B—H166109.5
C14B—C13—H133114.2
C11—C12—C13—C14A−119.6 (3)C11—C12—C13—C14B−91.3 (5)
C12—C13—C14A—C15A−178.3 (3)C12—C13—C14B—C15B176.4 (8)
C13—C14A—C15A—C16A180.0 (5)C13—C14B—C15B—C16B63.1 (17)
(bI) 1-n-Butylindeno[2,1-c]pyran-3,9-dione top
Crystal data top
C16H14O3F(000) = 268
Mr = 254.27Dx = 1.387 Mg m−3
Triclinic, P1Melting point: 373.7(5) K
a = 5.3708 (2) ÅMo Kα radiation, λ = 0.71073 Å
b = 7.2029 (3) ÅCell parameters from 1676 reflections
c = 16.9507 (8) Åθ = 2.4–29.8°
α = 96.461 (2)°µ = 0.10 mm−1
β = 93.246 (2)°T = 120 K
γ = 110.029 (2)°Irregular, colourless
V = 608.98 (4) Å30.30 × 0.12 × 0.10 mm
Z = 2
Data collection top
Bruker SMART CCD 6000 area-detector
diffractometer		1491 reflections with I > 2σ(I)
Radiation source: sealed X-ray tubeRint = 0.047
Graphite monochromatorθmax = 25.0°, θmin = 1.2°
Detector resolution: 5.6 pixels mm-1h = −6→6
ω scansk = −8→8
5759 measured reflectionsl = −20→20
2151 independent 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)] = 0.037Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.091H-atom parameters constrained
S = 0.96 w = 1/[σ2(Fo2) + (0.0452P)2]
where P = (Fo2 + 2Fc2)/3
2151 reflections(Δ/σ)max < 0.001
174 parametersΔρmax = 0.18 e Å−3
0 restraintsΔρmin = −0.21 e Å−3
Crystal data top
C16H14O3γ = 110.029 (2)°
Mr = 254.27V = 608.98 (4) Å3
Triclinic, P1Z = 2
a = 5.3708 (2) ÅMo Kα radiation
b = 7.2029 (3) ŵ = 0.10 mm−1
c = 16.9507 (8) ÅT = 120 K
α = 96.461 (2)°0.30 × 0.12 × 0.10 mm
β = 93.246 (2)°
Data collection top
Bruker SMART CCD 6000 area-detector
diffractometer		1491 reflections with I > 2σ(I)
5759 measured reflectionsRint = 0.047
2151 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0370 restraints
wR(F2) = 0.091H-atom parameters constrained
S = 0.96Δρmax = 0.18 e Å−3
2151 reflectionsΔρmin = −0.21 e Å−3
174 parameters
Special details top

Experimental. The data collection nominally covered a full sphere of reciprocal space by a combination of 4 sets of ω scans each set at different φ and/or 2θ angles and each scan (20 s exposure) covering -0.3° in ω. The crystal to detector distance was 4.84 cm.

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.3331 (2)0.67093 (18)0.29843 (7)0.0236 (3)
O20.5366 (2)0.71270 (19)0.42052 (7)0.0289 (3)
O3−0.2151 (2)0.86789 (19)0.14982 (7)0.0275 (3)
C10.3900 (4)0.7650 (3)0.37911 (10)0.0231 (4)
C20.2712 (3)0.9115 (3)0.40094 (10)0.0231 (4)
H20.30460.98030.45380.028*
C30.1122 (3)0.9510 (3)0.34607 (10)0.0206 (4)
C4−0.0241 (3)1.0975 (3)0.35064 (10)0.0208 (4)
C5−0.0283 (4)1.2378 (3)0.41299 (11)0.0252 (4)
H50.06811.25200.46340.030*
C6−0.1772 (4)1.3568 (3)0.39975 (11)0.0270 (5)
H6−0.18551.45200.44220.032*
C7−0.3154 (4)1.3399 (3)0.32539 (11)0.0257 (5)
H7−0.41451.42440.31780.031*
C8−0.3092 (4)1.2009 (3)0.26266 (11)0.0237 (4)
H8−0.40231.18900.21190.028*
C9−0.1631 (3)1.0795 (3)0.27606 (10)0.0202 (4)
C10−0.1218 (3)0.9212 (3)0.21951 (10)0.0212 (4)
C110.0560 (3)0.8461 (3)0.26607 (10)0.0203 (4)
C120.1700 (3)0.7116 (3)0.24340 (10)0.0212 (4)
C130.1431 (4)0.6016 (3)0.16156 (10)0.0271 (5)
H1310.22450.70040.12580.032*
H132−0.04910.54010.14300.032*
C140.2644 (4)0.4394 (3)0.15111 (10)0.0238 (4)
H1410.45860.49890.16690.029*
H1420.18640.33900.18660.029*
C150.2150 (4)0.3371 (3)0.06527 (11)0.0308 (5)
H1510.28640.43910.02980.037*
H1520.02050.27440.05040.037*
C160.3418 (4)0.1780 (3)0.05116 (11)0.0312 (5)
H1610.30270.1179−0.00500.041 (3)*
H1620.26920.07450.08510.041 (3)*
H1630.53510.23930.06440.041 (3)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0266 (7)0.0250 (7)0.0218 (7)0.0141 (6)−0.0015 (5)−0.0002 (6)
O20.0320 (8)0.0337 (8)0.0265 (7)0.0200 (7)−0.0032 (6)0.0030 (6)
O30.0341 (8)0.0309 (8)0.0196 (7)0.0159 (6)−0.0022 (6)−0.0005 (6)
C10.0240 (10)0.0232 (10)0.0209 (10)0.0074 (9)0.0008 (8)0.0009 (9)
C20.0248 (10)0.0241 (10)0.0208 (10)0.0107 (9)0.0004 (8)−0.0009 (8)
C30.0205 (10)0.0192 (10)0.0214 (10)0.0061 (8)0.0029 (7)0.0018 (8)
C40.0214 (10)0.0190 (10)0.0224 (10)0.0074 (8)0.0029 (8)0.0028 (8)
C50.0284 (11)0.0245 (11)0.0231 (10)0.0113 (9)0.0003 (8)0.0001 (9)
C60.0322 (11)0.0206 (11)0.0284 (11)0.0122 (9)0.0014 (9)−0.0044 (9)
C70.0266 (11)0.0223 (10)0.0323 (11)0.0134 (9)0.0042 (8)0.0046 (9)
C80.0247 (10)0.0230 (10)0.0244 (10)0.0090 (9)0.0011 (8)0.0054 (9)
C90.0209 (10)0.0191 (10)0.0211 (10)0.0075 (8)0.0022 (7)0.0032 (8)
C100.0210 (10)0.0216 (10)0.0205 (10)0.0066 (8)0.0028 (8)0.0035 (8)
C110.0205 (10)0.0209 (10)0.0192 (9)0.0073 (8)0.0010 (7)0.0021 (8)
C120.0197 (10)0.0219 (10)0.0226 (10)0.0082 (8)0.0019 (7)0.0030 (8)
C130.0314 (11)0.0302 (11)0.0221 (10)0.0164 (9)0.0000 (8)−0.0026 (9)
C140.0260 (10)0.0223 (10)0.0238 (10)0.0098 (8)0.0029 (8)0.0020 (8)
C150.0349 (12)0.0352 (12)0.0254 (11)0.0194 (10)−0.0013 (8)−0.0031 (9)
C160.0413 (12)0.0342 (12)0.0221 (10)0.0211 (10)0.0016 (9)−0.0037 (9)
Geometric parameters (Å, º) top
O1—C121.367 (2)C8—H80.9500
O1—C11.423 (2)C9—C101.490 (2)
O2—C11.206 (2)C10—C111.481 (2)
O3—C101.222 (2)C11—C121.345 (2)
C1—C21.435 (2)C12—C131.492 (2)
C2—C31.346 (2)C13—C141.519 (2)
C2—H20.9499C13—H1310.9900
C3—C111.438 (2)C13—H1320.9900
C3—C41.473 (2)C14—C151.520 (2)
C4—C51.385 (2)C14—H1410.9900
C4—C91.401 (2)C14—H1420.9900
C5—C61.384 (2)C15—C161.525 (2)
C5—H50.9500C15—H1510.9901
C6—C71.397 (3)C15—H1520.9900
C6—H60.9500C16—H1610.9800
C7—C81.386 (3)C16—H1620.9800
C7—H70.9499C16—H1630.9800
C8—C91.388 (2)
C12—O1—C1123.11 (13)C12—C11—C3120.68 (15)
O2—C1—O1115.30 (15)C12—C11—C10130.43 (16)
O2—C1—C2128.03 (17)C3—C11—C10108.81 (14)
O1—C1—C2116.66 (15)C11—C12—O1118.92 (16)
C3—C2—C1119.63 (17)C11—C12—C13126.38 (16)
C3—C2—H2120.2O1—C12—C13114.68 (15)
C1—C2—H2120.2C12—C13—C14117.56 (15)
C2—C3—C11120.94 (16)C12—C13—H131107.9
C2—C3—C4131.19 (17)C14—C13—H131107.9
C11—C3—C4107.85 (14)C12—C13—H132107.9
C5—C4—C9120.68 (17)C14—C13—H132107.9
C5—C4—C3130.91 (16)H131—C13—H132107.2
C9—C4—C3108.40 (15)C13—C14—C15111.58 (15)
C6—C5—C4118.08 (17)C13—C14—H141109.3
C6—C5—H5121.0C15—C14—H141109.3
C4—C5—H5121.0C13—C14—H142109.3
C5—C6—C7121.45 (17)C15—C14—H142109.3
C5—C6—H6119.3H141—C14—H142108.0
C7—C6—H6119.3C14—C15—C16113.51 (15)
C8—C7—C6120.55 (17)C14—C15—H151108.9
C8—C7—H7119.7C16—C15—H151108.9
C6—C7—H7119.7C14—C15—H152108.9
C7—C8—C9118.13 (16)C16—C15—H152108.9
C7—C8—H8120.9H151—C15—H152107.7
C9—C8—H8120.9C15—C16—H161109.5
C8—C9—C4121.10 (17)C15—C16—H162109.5
C8—C9—C10128.99 (15)H161—C16—H162109.5
C4—C9—C10109.90 (15)C15—C16—H163109.5
O3—C10—C11128.33 (16)H161—C16—H163109.5
O3—C10—C9126.65 (16)H162—C16—H163109.5
C11—C10—C9105.02 (14)
O1—C12—C13—C148.3 (2)C13—C14—C15—C16177.91 (17)
C12—C13—C14—C15178.49 (16)
(bIRT) 1-n-Butylindeno[2,1-c]pyran-3,9-dione top
Crystal data top
C16H14O3Z = 2
Mr = 254.27F(000) = 268
Triclinic, P1Dx = 1.337 Mg m−3
a = 5.4330 (3) ÅMo Kα radiation, λ = 0.71073 Å
b = 7.2863 (4) ÅCell parameters from 1474 reflections
c = 17.0874 (9) Åθ = 2.4–22.8°
α = 97.426 (2)°µ = 0.09 mm−1
β = 92.884 (2)°T = 293 K
γ = 108.874 (2)°Irregular, colourless
V = 631.62 (6) Å30.30 × 0.12 × 0.10 mm
Data collection top
Bruker SMART CCD 6000 area-detector
diffractometer		1138 reflections with I > 2σ(I)
Radiation source: sealed X-ray tubeRint = 0.039
Graphite monochromatorθmax = 25.0°, θmin = 1.2°
Detector resolution: 5.6 pixels mm-1h = −6→6
ω scansk = −8→8
6510 measured reflectionsl = −20→20
2222 independent 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)] = 0.039Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.096H-atom parameters constrained
S = 0.84 w = 1/[σ2(Fo2) + (0.0473P)2]
where P = (Fo2 + 2Fc2)/3
2222 reflections(Δ/σ)max < 0.001
174 parametersΔρmax = 0.20 e Å−3
0 restraintsΔρmin = −0.11 e Å−3
Crystal data top
C16H14O3γ = 108.874 (2)°
Mr = 254.27V = 631.62 (6) Å3
Triclinic, P1Z = 2
a = 5.4330 (3) ÅMo Kα radiation
b = 7.2863 (4) ŵ = 0.09 mm−1
c = 17.0874 (9) ÅT = 293 K
α = 97.426 (2)°0.30 × 0.12 × 0.10 mm
β = 92.884 (2)°
Data collection top
Bruker SMART CCD 6000 area-detector
diffractometer		1138 reflections with I > 2σ(I)
6510 measured reflectionsRint = 0.039
2222 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0390 restraints
wR(F2) = 0.096H-atom parameters constrained
S = 0.84Δρmax = 0.20 e Å−3
2222 reflectionsΔρmin = −0.11 e Å−3
174 parameters
Special details top

Experimental. The data collection nominally covered a full sphere of reciprocal space by a combination of 4 sets of ω scans each set at different φ and/or 2θ angles and each scan (20 s exposure) covering -0.3° in ω. The crystal to detector distance was 4.85 cm.

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.3367 (3)0.6718 (2)0.29864 (8)0.0580 (4)
O20.5369 (3)0.7157 (2)0.41943 (9)0.0731 (5)
O3−0.2037 (3)0.8665 (2)0.15197 (9)0.0702 (5)
C10.3923 (4)0.7667 (3)0.37858 (13)0.0566 (6)
C20.2737 (4)0.9127 (3)0.40021 (12)0.0549 (6)
H20.30470.98050.45170.066*
C30.1170 (4)0.9515 (3)0.34585 (11)0.0481 (5)
C4−0.0197 (4)1.0962 (3)0.35063 (12)0.0482 (5)
C5−0.0275 (4)1.2364 (3)0.41260 (13)0.0627 (6)
H50.06501.25100.46160.075*
C6−0.1753 (4)1.3538 (3)0.39990 (14)0.0678 (7)
H6−0.18471.44720.44120.081*
C7−0.3105 (4)1.3354 (3)0.32665 (14)0.0649 (7)
H7−0.40771.41710.31930.078*
C8−0.3019 (4)1.1967 (3)0.26453 (13)0.0606 (6)
H8−0.39261.18390.21540.073*
C9−0.1559 (4)1.0775 (3)0.27695 (12)0.0486 (5)
C10−0.1122 (4)0.9202 (3)0.22093 (12)0.0512 (6)
C110.0628 (4)0.8464 (3)0.26681 (11)0.0475 (5)
C120.1738 (4)0.7110 (3)0.24442 (12)0.0513 (6)
C130.1471 (5)0.5983 (3)0.16367 (13)0.0699 (7)
H1310.22050.69170.12830.084*
H132−0.03810.53900.14660.084*
C140.2673 (4)0.4402 (3)0.15115 (12)0.0619 (6)
H1410.19710.34520.18620.074*
H1420.45430.49750.16550.074*
C150.2188 (5)0.3354 (4)0.06698 (14)0.0784 (8)
H1510.03170.27410.05360.094*
H1520.28150.43180.03200.094*
C160.3462 (5)0.1808 (4)0.05112 (14)0.0859 (8)
H1610.30300.1199−0.00330.125 (6)*
H1620.28440.08340.08490.125 (6)*
H1630.53230.24050.06170.125 (6)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0651 (10)0.0619 (10)0.0530 (9)0.0349 (8)−0.0056 (7)−0.0013 (8)
O20.0826 (12)0.0840 (12)0.0650 (11)0.0503 (10)−0.0147 (9)0.0052 (9)
O30.0859 (12)0.0811 (12)0.0475 (10)0.0406 (10)−0.0115 (8)−0.0028 (9)
C10.0613 (15)0.0589 (15)0.0498 (14)0.0251 (13)−0.0046 (11)−0.0007 (12)
C20.0605 (14)0.0598 (15)0.0460 (13)0.0268 (12)−0.0030 (11)−0.0007 (11)
C30.0500 (13)0.0465 (13)0.0476 (13)0.0180 (11)0.0001 (10)0.0033 (11)
C40.0512 (13)0.0447 (13)0.0501 (13)0.0199 (11)0.0014 (10)0.0026 (11)
C50.0720 (16)0.0576 (15)0.0603 (15)0.0304 (13)−0.0037 (12)−0.0041 (13)
C60.0782 (17)0.0567 (15)0.0717 (17)0.0340 (14)0.0011 (14)−0.0061 (13)
C70.0711 (17)0.0539 (15)0.0791 (17)0.0352 (13)0.0027 (13)0.0080 (14)
C80.0648 (15)0.0602 (15)0.0620 (15)0.0282 (13)−0.0006 (12)0.0119 (13)
C90.0527 (13)0.0461 (13)0.0503 (13)0.0224 (11)0.0001 (10)0.0051 (11)
C100.0536 (14)0.0539 (14)0.0462 (14)0.0195 (11)0.0002 (11)0.0059 (11)
C110.0519 (14)0.0486 (13)0.0436 (13)0.0212 (12)0.0004 (10)0.0030 (11)
C120.0501 (13)0.0544 (14)0.0486 (13)0.0198 (12)−0.0003 (10)0.0011 (11)
C130.0828 (18)0.0798 (17)0.0540 (14)0.0462 (15)−0.0055 (12)−0.0104 (13)
C140.0697 (16)0.0581 (15)0.0589 (15)0.0273 (13)0.0066 (11)−0.0027 (12)
C150.0901 (19)0.0877 (19)0.0627 (16)0.0481 (16)−0.0019 (13)−0.0147 (14)
C160.111 (2)0.094 (2)0.0629 (16)0.0582 (19)0.0006 (14)−0.0138 (15)
Geometric parameters (Å, º) top
O1—C121.369 (2)C8—H80.9299
O1—C11.419 (2)C9—C101.484 (3)
O2—C11.201 (2)C10—C111.474 (3)
O3—C101.218 (2)C11—C121.339 (3)
C1—C21.432 (3)C12—C131.486 (3)
C2—C31.346 (3)C13—C141.495 (3)
C2—H20.9301C13—H1310.9700
C3—C111.429 (3)C13—H1320.9700
C3—C41.470 (3)C14—C151.506 (3)
C4—C51.385 (3)C14—H1410.9700
C4—C91.396 (3)C14—H1420.9700
C5—C61.378 (3)C15—C161.505 (3)
C5—H50.9299C15—H1510.9700
C6—C71.387 (3)C15—H1520.9699
C6—H60.9299C16—H1610.9599
C7—C81.381 (3)C16—H1620.9600
C7—H70.9300C16—H1630.9600
C8—C91.380 (3)
C12—O1—C1123.01 (16)C12—C11—C3120.61 (18)
O2—C1—O1115.49 (19)C12—C11—C10130.41 (18)
O2—C1—C2128.1 (2)C3—C11—C10108.92 (17)
O1—C1—C2116.39 (18)C11—C12—O1119.13 (18)
C3—C2—C1119.80 (19)C11—C12—C13126.63 (18)
C3—C2—H2120.1O1—C12—C13114.21 (17)
C1—C2—H2120.1C12—C13—C14119.14 (18)
C2—C3—C11121.01 (18)C12—C13—H131107.5
C2—C3—C4131.27 (19)C14—C13—H131107.5
C11—C3—C4107.71 (16)C12—C13—H132107.5
C5—C4—C9120.35 (19)C14—C13—H132107.5
C5—C4—C3131.12 (19)H131—C13—H132107.0
C9—C4—C3108.52 (17)C13—C14—C15113.21 (19)
C6—C5—C4118.4 (2)C13—C14—H141108.9
C6—C5—H5120.8C15—C14—H141108.9
C4—C5—H5120.8C13—C14—H142108.9
C5—C6—C7121.2 (2)C15—C14—H142108.9
C5—C6—H6119.4H141—C14—H142107.7
C7—C6—H6119.4C16—C15—C14114.9 (2)
C8—C7—C6120.6 (2)C16—C15—H151108.6
C8—C7—H7119.7C14—C15—H151108.6
C6—C7—H7119.7C16—C15—H152108.6
C9—C8—C7118.6 (2)C14—C15—H152108.5
C9—C8—H8120.7H151—C15—H152107.5
C7—C8—H8120.7C15—C16—H161109.5
C8—C9—C4120.87 (19)C15—C16—H162109.5
C8—C9—C10129.45 (19)H161—C16—H162109.5
C4—C9—C10109.68 (17)C15—C16—H163109.5
O3—C10—C11128.54 (19)H161—C16—H163109.5
O3—C10—C9126.31 (18)H162—C16—H163109.5
C11—C10—C9105.16 (17)
C11—C12—C13—C14−174.8 (2)C13—C14—C15—C16177.5 (2)
C12—C13—C14—C15178.5 (2)

Experimental details

(aI)(bI)(bIRT)
Crystal data
Chemical formulaC16H14O3C16H14O3C16H14O3
Mr254.27254.27254.27
Crystal system, space groupTriclinic, P1Triclinic, P1Triclinic, P1
Temperature (K)293120293
a, b, c (Å)4.6539 (6), 10.1800 (12), 14.3718 (17)5.3708 (2), 7.2029 (3), 16.9507 (8)5.4330 (3), 7.2863 (4), 17.0874 (9)
α, β, γ (°)82.481 (5), 88.127 (7), 78.604 (6)96.461 (2), 93.246 (2), 110.029 (2)97.426 (2), 92.884 (2), 108.874 (2)
V (Å3)661.71 (14)608.98 (4)631.62 (6)
Z222
Radiation typeMo KαMo KαMo Kα
µ (mm−1)0.090.100.09
Crystal size (mm)0.22 × 0.18 × 0.060.30 × 0.12 × 0.100.30 × 0.12 × 0.10
Data collection
DiffractometerBruker SMART CCD 6000 area-detectorBruker SMART CCD 6000 area-detectorBruker SMART CCD 6000 area-detector
Absorption correction–––
No. of measured, independent and
observed [I > 2σ(I)] reflections		5329, 2336, 1137 5759, 2151, 1491 6510, 2222, 1138
Rint0.0630.0470.039
(sin θ/λ)max (Å−1)0.5950.5950.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.041, 0.110, 0.84 0.037, 0.091, 0.96 0.039, 0.096, 0.84
No. of reflections233621512222
No. of parameters185174174
No. of restraints1500
H-atom treatmentH-atom parameters constrainedH-atom parameters constrainedH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.10, −0.140.18, −0.210.20, −0.11

Computer programs: SMART (Bruker, 2001), SMART (Bruker, 2003), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), OLEX2 (Dolomanov et al., 2009).

 

Subscribe to Acta Crystallographica Section C: Structural Chemistry

The full text of this article is available to subscribers to the journal.

If you have already registered and are using a computer listed in your registration details, please email support@iucr.org for assistance.

Buy online

You may purchase this article in PDF and/or HTML formats. For purchasers in the European Community who do not have a VAT number, VAT will be added at the local rate. Payments to the IUCr are handled by WorldPay, who will accept payment by credit card in several currencies. To purchase the article, please complete the form below (fields marked * are required), and then click on `Continue'.
E-mail address* 
Repeat e-mail address* 
(for error checking) 

Format*   PDF (US $40)
   HTML (US $40)
   PDF+HTML (US $50)
In order for VAT to be shown for your country javascript needs to be enabled.

VAT number 
(non-UK EC countries only) 
Country* 
 

Terms and conditions of use
Contact us

Follow Acta Cryst. C
Sign up for e-alerts
E-alerts
Follow Acta Cryst. on Twitter
Twitter
Follow us on facebook
Facebook
Sign up for RSS feeds
RSS