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The two title chromene compounds, 3,3a-dihydrocyclo­penta­[b]chromen-1(2H)-one, C16H12O2, (I), and 2-(2-hydroxy­benzyl­idene)-3,3a-dihydrocyclo­penta­[b]chromen-1(2H)-one, C19H14O3, (II), have been determined in the monoclinic space group P21/n. Compound (I) is mainly stabilized by C-H...[pi] inter­actions. Compound (II) is linked into infinite one-dimensional chains with a C(3) motif via inter­molecular O-H...O hydrogen bonds. The inter­molecular C-H...[pi] and [pi][pi] inter­actions also play key roles in stabilizing the crystal packing. Two intra­molecular C-H...O hydrogen bonds with S(5) motifs were detected in (II).

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270105008528/sk1811sup1.cif
Contains datablocks I, II, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270105008528/sk1811Isup2.hkl
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270105008528/sk1811IIsup3.hkl
Contains datablock II

CCDC references: 273072; 273073

Comment top

Chromenes (2H-1-benzopyrane derivatives) are frequently found in naturally occurring heterocycles, many of which exhibit biological activity (Bowers et al., 1976) and have been widely employed as important intermediates in the synthesis of many natural products and medicinal agents (Wang & Finn, 2000). Thus, various synthetic methods for the formation of these compounds have been reported (Kaye & Nocanda, 2000; Parker & Mindt, 2001).

Most recently, the reaction of 2-hydroxybenzaldehyde and cyclopent-2-enone, a typical Baylis–Hillman coupling, was suggested to occur through a domino oxa-Michael addition/aldol condesation pathway in the presence of DMAP (dimethylaminopyridine; Lee et al., 2003) or DABCO (diazabicyclo[2.2.2]octane; Bräse & Lesch, 2004) under aqueous conditions. We have also carried out the reactions with imidazole as a catalyst. Several crystal structures of chromene derivatives have been published (Huo et al., 2004a,b,c). In the present paper, another two crystal stuctures are reported.

In the five derivatives that we have studied [7a,8,9,10-tetrahydrobenzo[f]cyclopenta[b]chromen-10-one (Huo et al., 2004a), nitro/methoxy-2,3-dihydro-1H-cyclopenta[b]chromen-1-one (Huo et al., 2004b,c), 3,3a-dihydro-2H-cyclopenta[b]chromen-1-one and 5-benzylidene-3,3a-dihydro-2H-cyclopenta[b]chromen-1-one (the present work)], similarities in the geometry are observed and the pyran ring has the same configuration (half-chair). However, the crystal packings for the five compounds differ, partly because of the presence of different substituents.

Selected geometric parameters of (I) are listed in Table 1. The ellipsoid plot of the molecule is shown in Fig. 1. Single-crystal X-ray analysis of the good quality single crystals revealed a monoclinic crystal lattice with a P21/n space group. Atom C3 of the pyran ring in disordered over two sites, with a ratio of 0.59 (6):0.41 (6) for the major and minor components, respectively. All atoms, except atom C3, are coplanar within ±0.0611 (2) Å, while atom C3 deviates from the plane of the other atoms by 0.4784 (3) Å. The pyran ring adopts a half-chair conformation, the dihedral angle between the O2/C3/C2 and O2/C8/C7/C6 planes being 38.02 (2)°. The C1—C2—C3—O2 and C6—C2—C3—O2 torsion angles are −152.7 (2) and 40.2 (3)°, respectively. For the minor component, the C1—C2—C3A—O2 and C6—C2—C3A—O2 torsion angles are 156.0 (2) and −43.2 (3)°. The packing of the crystals indicates that the adjacent molecules show two C—H···π (edge-to-face) interactions, elucidated by PLATON (Spek, 2003), with the π system of the C7–C12 ring (with centroid Cg; Fig. 2). In the first of these interactions, the cyclopentene ring atom C5 interacts with Cg at (x, 1 + y, z) [C5···Cg = 3.776 (2) Å, H5A···Cg = 2.89 Å and C5—H5A···Cg = 153°]. In the second interaction, phenyl atom C10 interacts with Cg at (3/2 − x, −1/2 + y, 1/2 − z) [C10···Cg = 3.901 (2) Å, H10···Cg = 3.22 Å and C10—H10···Cg = 132°]. Selected geometric parameters of (II) are listed in Table 2. The ellipsoid plot of the molecule is shown in Fig. 3. Single-crystal X-ray analysis of the crystals of (II) revealed a monoclinic crystal lattice with a P21/n space group. The chromene fragment of the molecule is the same as that of (I). Except for atom C3, all atoms are coplanar within ±0.187 (2) Å, with atom C3 deviating by 0.4051 (2) Å. The dihedral angel between the O2/C3/C2 and O2/C8/C7/C6 planes is 35.51 (2)°. The The C1—C2—C3—O2 and C6—C2—C3—C4 torsion angles are 146.9 (2) and −151.0 (2)°, respectively. The C14–C19 phenyl ring and the chromene fragment are joined by atom C13. The C14—C13—C5—C4 and C5—C13—C14—C19 torsion angles are −5.6 (3) and −23.4 (3)°. A linear O—H···O intermolecular hydrogen bond of the hydroxy group was observed in the crystal structure of II (Fig. 4). The strong interaction links the molecules into an infinite one-dimensional chain-based vector [101], with a C(3) motif (Bernstein et al., 1995). The hydrogen-bonding parameters include an H1···O1 distance of 1.93 Å and an O3—H1···O1 angle of 178° (Table 3). Further detection indicates that the crystal has two intramolecular C—H···O hydrogen bonds (Table 3), with the sp2 C13 atom acting as the only donor, and the carbonyl O atom and hydroxy O atom playing as acceptors. The O1···H13···O3 angle is 153.30°. Furthermore, the three intermolecular C—H···π interactions (Table 3; Cg1 is the centroid of the C14–C19 ring, and Cg2 the centroid of the C7–C12 ring) and ππ interactions are detected, which stabilize the crystal stacking. Fig. 5 shows the two C—H···π (edge-to-face) interactions related to the π electrons of the C14–C19 phenyl ring (with centroid Cg1).

Experimental top

The title compounds were synthesized from Baylis–Hillman reactions. At room temperature, a clear solution of 2-hydroxybenzaldehyde (1 mmol), cyclopent-2-enone (2 mmol) and imidazole (1 mmol) in tetrahydrofuran (1.5 ml) was mixed with deionized water (1.5 ml). The mixture was stirred at ambient temperature for 48 h to finish the reaction. The mixture was diluted with water (10 ml) and extracted with ethyl acetate. The organic layer was concentrated under reduced pressure. After the usual work up, chromatography of the crude product on silica gel, using ethyl acetate and petroleum (1:4) as eluant, gave pure (I) with a yield of 53% and a little (II). Compound (I) (60 mg) was dissolved in CHCl3 (2 ml). The solution was allowed to evaporate slowly at room temperature for several days. Yellow crystals suitable for X-ray crystallography were formed. Crystals of (II) were formed during the processes of chromatography.

Refinement top

All H atoms were placed in calculated positions and allowed to ride on their parent atoms, with Uiso(H) values set to 1.5Ueq(parent atom) for the Csp3-bound H atoms and the hydroxy-group O atom, and 1.2Ueq(parent atom) for Csp2-bound H atoms. The C—H distances were fixed in the range 0.93–0.98 Å and O—H distances were fixed at 0.82 Å.

Computing details top

For both compounds, data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2000); software used to prepare material for publication: SHELXTL.

Figures top
[Figure 1] Fig. 1. A view of the molecular structure of (I), with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. The suffix A denotes the 41% minor disorder component.
[Figure 2] Fig. 2. The packing of (I), viewed down the a axis. C5—H5A···Cg(x, 1 + y, z) and C10—H10···Cg(3/2 − x, −1/2 + y, 1/2 − z) interactions are indicated by dotted lines. The minor component of the disorder has been omitted for clarity.
[Figure 3] Fig. 3. A view of the molecular structure of (II). Displacement ellipsoids are shown at the 50% probability level.
[Figure 4] Fig. 4. The packing of (II). Infinite one-dimensional O—H···Oi hydrogen-bonding chains along the [101] orientation are indicated with dotted lines. The view is down the a axis. [Symmetry code: (i) −1/2 + x, 5/2 − y, −1/2 + z.]
[Figure 5] Fig. 5. C6—H6···Cg1ii and C3—H3···Cg1iii [symmetry codes: (ii) 2 − x, 2 − y, −z; (iii) 1 − x, 2 − y, −z; Cg1 is the centroid of the C14–C19 ring) interactions in the structure of (II). Selected atoms are labled. H atoms, except atoms H3 and H6, have been omitted for clarity.
(I) 3,3a-dihydro-2H-cyclopenta[b]chromen-1-one top
Crystal data top
C12H10O2F(000) = 392
Mr = 186.20Dx = 1.353 Mg m3
Monoclinic, P21/nMelting point: 388 K
Hall symbol: -P 2ynMo Kα radiation, λ = 0.71073 Å
a = 5.8015 (14) ÅCell parameters from 5211 reflections
b = 7.6260 (19) Åθ = 2.9–26.9°
c = 20.661 (5) ŵ = 0.09 mm1
β = 91.254 (3)°T = 298 K
V = 913.9 (4) Å3Block, yellow
Z = 40.73 × 0.25 × 0.25 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer
1579 independent reflections
Radiation source: fine-focus sealed tube1324 reflections with I > 2 σ(I)
Graphite monochromatorRint = 0.016
Detector resolution: 100x100 microns pixels mm-1θmax = 25.0°, θmin = 2.0°
ω scansh = 65
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
k = 89
Tmin = 0.723, Tmax = 0.978l = 2124
4188 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)] = 0.046Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.126H-atom parameters constrained
S = 1.04 w = 1/[σ2(Fo2) + (0.0656P)2 + 0.2252P]
where P = (Fo2 + 2Fc2)/3
1579 reflections(Δ/σ)max < 0.001
137 parametersΔρmax = 0.24 e Å3
3 restraintsΔρmin = 0.22 e Å3
Crystal data top
C12H10O2V = 913.9 (4) Å3
Mr = 186.20Z = 4
Monoclinic, P21/nMo Kα radiation
a = 5.8015 (14) ŵ = 0.09 mm1
b = 7.6260 (19) ÅT = 298 K
c = 20.661 (5) Å0.73 × 0.25 × 0.25 mm
β = 91.254 (3)°
Data collection top
Bruker SMART CCD area-detector
diffractometer
1579 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
1324 reflections with I > 2 σ(I)
Tmin = 0.723, Tmax = 0.978Rint = 0.016
4188 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0463 restraints
wR(F2) = 0.126H-atom parameters constrained
S = 1.04Δρmax = 0.24 e Å3
1579 reflectionsΔρmin = 0.22 e Å3
137 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*/UeqOcc. (<1)
O10.7229 (3)1.2583 (2)0.00041 (8)0.0842 (5)
O21.1469 (2)0.94154 (15)0.15970 (6)0.0564 (4)
C10.8706 (3)1.2221 (2)0.04004 (8)0.0535 (5)
C20.8769 (3)1.0640 (2)0.08027 (9)0.0555 (5)
C31.0474 (5)1.0996 (3)0.13654 (13)0.0491 (10)0.587 (6)
H30.96681.15780.17180.074*0.587 (6)
C3A1.1313 (5)1.0401 (4)0.10213 (15)0.0514 (15)0.413 (6)
H3A1.21530.97970.06800.077*0.413 (6)
C41.2154 (4)1.2241 (3)0.10787 (10)0.0649 (5)
H4A1.34001.16050.08790.097*0.587 (6)
H4B1.28051.30070.14100.097*0.587 (6)
H4AA1.37931.22980.09980.097*0.413 (6)
H4AB1.18871.26930.15090.097*0.413 (6)
C51.0803 (4)1.3303 (3)0.05733 (9)0.0617 (5)
H5A1.03551.44280.07490.093*
H5B1.17261.35020.01940.093*
C60.7411 (3)0.9270 (2)0.08357 (8)0.0482 (4)
H60.61140.91840.05650.058*
C70.7943 (3)0.7895 (2)0.12959 (8)0.0443 (4)
C81.0000 (3)0.8026 (2)0.16646 (7)0.0433 (4)
C91.0582 (3)0.6754 (2)0.21136 (8)0.0520 (5)
H91.19630.68350.23490.062*
C100.9125 (3)0.5369 (2)0.22138 (9)0.0591 (5)
H100.95110.45240.25220.071*
C110.7090 (4)0.5222 (3)0.18601 (11)0.0670 (6)
H110.61030.42850.19330.080*
C120.6519 (3)0.6464 (3)0.13994 (10)0.0599 (5)
H120.51630.63420.11550.072*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0761 (10)0.0796 (10)0.0955 (11)0.0037 (8)0.0321 (9)0.0362 (9)
O20.0506 (7)0.0523 (7)0.0652 (8)0.0044 (5)0.0207 (6)0.0086 (6)
C10.0580 (11)0.0511 (10)0.0513 (10)0.0050 (8)0.0017 (9)0.0043 (8)
C20.0545 (10)0.0550 (10)0.0562 (10)0.0053 (8)0.0182 (8)0.0086 (8)
C30.059 (2)0.0443 (17)0.0431 (18)0.0017 (13)0.0101 (14)0.0010 (13)
C3A0.057 (3)0.051 (3)0.046 (3)0.003 (2)0.006 (2)0.0069 (19)
C40.0600 (11)0.0590 (12)0.0749 (13)0.0111 (9)0.0142 (9)0.0077 (9)
C50.0728 (13)0.0525 (10)0.0594 (11)0.0081 (9)0.0044 (10)0.0051 (9)
C60.0373 (9)0.0559 (10)0.0509 (9)0.0024 (7)0.0081 (7)0.0031 (8)
C70.0420 (9)0.0470 (9)0.0439 (9)0.0017 (7)0.0017 (7)0.0007 (7)
C80.0431 (9)0.0445 (9)0.0422 (9)0.0032 (7)0.0024 (7)0.0043 (7)
C90.0539 (10)0.0549 (10)0.0467 (9)0.0085 (8)0.0084 (8)0.0016 (8)
C100.0731 (12)0.0549 (11)0.0492 (10)0.0062 (9)0.0023 (9)0.0095 (8)
C110.0682 (12)0.0621 (12)0.0707 (13)0.0133 (10)0.0021 (10)0.0157 (10)
C120.0504 (10)0.0636 (11)0.0651 (11)0.0105 (9)0.0076 (8)0.0074 (9)
Geometric parameters (Å, º) top
O1—C11.204 (2)C4—H4AA0.9700
O2—C81.369 (2)C4—H4AB0.9700
O2—C3A1.408 (3)C5—H5A0.9700
O2—C31.415 (3)C5—H5B0.9700
C1—C21.464 (2)C6—C71.444 (2)
C1—C51.506 (3)C6—H60.9300
C2—C61.312 (2)C7—C121.388 (2)
C2—C31.534 (3)C7—C81.405 (2)
C2—C3A1.544 (3)C8—C91.379 (2)
C3—C41.493 (3)C9—C101.371 (3)
C3—H30.9800C9—H90.9300
C3A—C41.490 (3)C10—C111.379 (3)
C3A—H3A0.9800C10—H100.9300
C4—C51.525 (3)C11—C121.378 (3)
C4—H4A0.9700C11—H110.9300
C4—H4B0.9700C12—H120.9300
C8—O2—C3A118.07 (15)C5—C4—H4AA110.4
C8—O2—C3116.33 (15)C3A—C4—H4AB110.4
O1—C1—C2125.69 (17)C3—C4—H4AB75.1
O1—C1—C5126.48 (17)C5—C4—H4AB110.4
C2—C1—C5107.83 (15)H4A—C4—H4AB134.8
C6—C2—C1132.68 (16)H4AA—C4—H4AB108.6
C6—C2—C3118.66 (16)C1—C5—C4105.79 (15)
C1—C2—C3107.00 (16)C1—C5—H5A110.6
C6—C2—C3A117.51 (17)C4—C5—H5A110.6
C1—C2—C3A105.97 (17)C1—C5—H5B110.6
O2—C3—C4114.26 (19)C4—C5—H5B110.6
O2—C3—C2110.92 (17)H5A—C5—H5B108.7
C4—C3—C2103.15 (17)C2—C6—C7119.51 (15)
O2—C3—H3109.4C2—C6—H6120.2
C4—C3—H3109.4C7—C6—H6120.2
C2—C3—H3109.4C12—C7—C8118.27 (15)
O2—C3A—C4114.9 (2)C12—C7—C6123.56 (15)
O2—C3A—C2110.71 (19)C8—C7—C6118.16 (15)
C4—C3A—C2102.78 (18)O2—C8—C9117.99 (15)
O2—C3A—H3A109.4O2—C8—C7121.53 (14)
C4—C3A—H3A109.4C9—C8—C7120.47 (16)
C2—C3A—H3A109.4C10—C9—C8120.04 (17)
C3A—C4—C5106.43 (17)C10—C9—H9120.0
C3—C4—C5106.21 (17)C8—C9—H9120.0
C3A—C4—H4A75.0C9—C10—C11120.39 (17)
C3—C4—H4A110.5C9—C10—H10119.8
C5—C4—H4A110.5C11—C10—H10119.8
C3A—C4—H4B138.2C12—C11—C10120.02 (18)
C3—C4—H4B110.5C12—C11—H11120.0
C5—C4—H4B110.5C10—C11—H11120.0
H4A—C4—H4B108.7C11—C12—C7120.78 (18)
C3A—C4—H4AA110.4C11—C12—H12119.6
C3—C4—H4AA138.4C7—C12—H12119.6
O1—C1—C2—C61.9 (4)C2—C3A—C4—C531.3 (2)
C5—C1—C2—C6178.3 (2)O2—C3—C4—C3A55.3 (2)
O1—C1—C2—C3162.7 (2)C2—C3—C4—C3A65.24 (17)
C5—C1—C2—C317.1 (2)O2—C3—C4—C5151.43 (19)
O1—C1—C2—C3A158.5 (2)C2—C3—C4—C530.9 (2)
C5—C1—C2—C3A21.7 (2)O1—C1—C5—C4178.0 (2)
C8—O2—C3—C4159.25 (17)C2—C1—C5—C42.2 (2)
C3A—O2—C3—C456.0 (2)C3A—C4—C5—C118.9 (2)
C8—O2—C3—C243.2 (2)C3—C4—C5—C121.2 (2)
C3A—O2—C3—C260.1 (2)C1—C2—C6—C7179.77 (19)
C6—C2—C3—O240.2 (3)C3—C2—C6—C716.6 (3)
C1—C2—C3—O2152.68 (18)C3A—C2—C6—C725.8 (3)
C3A—C2—C3—O258.48 (19)C2—C6—C7—C12174.99 (18)
C6—C2—C3—C4162.92 (18)C2—C6—C7—C84.1 (2)
C1—C2—C3—C429.9 (2)C3A—O2—C8—C9160.18 (19)
C3A—C2—C3—C464.27 (17)C3—O2—C8—C9153.84 (17)
C8—O2—C3A—C4155.23 (18)C3A—O2—C8—C720.6 (2)
C3—O2—C3A—C456.6 (2)C3—O2—C8—C725.4 (2)
C8—O2—C3A—C239.4 (3)C12—C7—C8—O2178.85 (16)
C3—O2—C3A—C259.3 (2)C6—C7—C8—O20.3 (2)
C6—C2—C3A—O243.2 (3)C12—C7—C8—C90.4 (2)
C1—C2—C3A—O2156.04 (19)C6—C7—C8—C9179.58 (15)
C3—C2—C3A—O258.8 (2)O2—C8—C9—C10177.77 (15)
C6—C2—C3A—C4166.34 (19)C7—C8—C9—C101.5 (3)
C1—C2—C3A—C432.9 (2)C8—C9—C10—C111.1 (3)
C3—C2—C3A—C464.32 (17)C9—C10—C11—C120.5 (3)
O2—C3A—C4—C356.1 (2)C10—C11—C12—C71.6 (3)
C2—C3A—C4—C364.24 (17)C8—C7—C12—C111.2 (3)
O2—C3A—C4—C5151.6 (2)C6—C7—C12—C11177.98 (18)
(II) 2-(2-hydroxybenzylidene)-3,3a-dihydro-2H-cyclopenta[b]chromen-1-one top
Crystal data top
C19H14O3F(000) = 608
Mr = 290.30Dx = 1.336 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 8693 reflections
a = 8.8978 (9) Åθ = 2.3–24.6°
b = 12.5893 (12) ŵ = 0.09 mm1
c = 13.1797 (13) ÅT = 298 K
β = 102.157 (2)°Block, orange
V = 1443.2 (2) Å30.36 × 0.23 × 0.23 mm
Z = 4
Data collection top
Bruker SMART CCD area-detector
diffractometer
2543 independent reflections
Radiation source: fine-focus sealed tube1881 reflections with I > 2 σ(I)
Graphite monochromatorRint = 0.056
Detector resolution: 100x100 microns pixels mm-1θmax = 25.0°, θmin = 2.3°
ω scansh = 1010
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
k = 1314
Tmin = 0.733, Tmax = 0.980l = 1512
5951 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)] = 0.051Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.135H-atom parameters constrained
S = 1.00 w = 1/[σ2(Fo2) + (0.0745P)2]
where P = (Fo2 + 2Fc2)/3
2543 reflections(Δ/σ)max < 0.001
200 parametersΔρmax = 0.43 e Å3
0 restraintsΔρmin = 0.17 e Å3
Crystal data top
C19H14O3V = 1443.2 (2) Å3
Mr = 290.30Z = 4
Monoclinic, P21/nMo Kα radiation
a = 8.8978 (9) ŵ = 0.09 mm1
b = 12.5893 (12) ÅT = 298 K
c = 13.1797 (13) Å0.36 × 0.23 × 0.23 mm
β = 102.157 (2)°
Data collection top
Bruker SMART CCD area-detector
diffractometer
2543 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
1881 reflections with I > 2 σ(I)
Tmin = 0.733, Tmax = 0.980Rint = 0.056
5951 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0510 restraints
wR(F2) = 0.135H-atom parameters constrained
S = 1.00Δρmax = 0.43 e Å3
2543 reflectionsΔρmin = 0.17 e Å3
200 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
O11.00662 (17)1.16604 (10)0.09244 (10)0.0488 (4)
O20.81915 (17)0.85477 (11)0.22844 (11)0.0580 (4)
O30.64722 (19)1.21752 (11)0.23748 (11)0.0613 (5)
C10.9278 (2)1.08728 (14)0.10067 (14)0.0384 (5)
C20.9320 (2)1.02399 (15)0.19441 (15)0.0417 (5)
C30.7922 (2)0.95434 (18)0.17692 (16)0.0536 (6)
C40.7471 (2)0.94132 (16)0.05991 (15)0.0502 (5)
C50.8097 (2)1.03955 (14)0.01691 (15)0.0383 (5)
C61.0387 (2)1.01663 (15)0.28121 (15)0.0419 (5)
C71.0237 (2)0.93498 (15)0.35556 (15)0.0423 (5)
C80.9087 (2)0.85840 (16)0.32677 (16)0.0462 (5)
C90.8888 (3)0.77979 (18)0.39612 (18)0.0608 (6)
C100.9832 (3)0.7764 (2)0.49356 (17)0.0620 (7)
C111.0996 (3)0.84881 (19)0.52178 (17)0.0593 (6)
C121.1191 (2)0.92764 (18)0.45361 (17)0.0548 (6)
C130.7717 (2)1.08290 (15)0.07750 (14)0.0401 (5)
C140.6668 (2)1.04355 (15)0.17031 (14)0.0381 (5)
C150.6116 (2)1.11356 (16)0.25240 (14)0.0416 (5)
C160.5238 (2)1.07604 (17)0.34508 (16)0.0501 (5)
C170.4918 (3)0.96939 (18)0.35754 (17)0.0526 (6)
C180.5437 (2)0.89901 (17)0.27783 (16)0.0521 (6)
C190.6293 (2)0.93556 (16)0.18566 (16)0.0463 (5)
H10.60681.25130.28920.092*
H30.70950.99140.20120.080*
H61.12161.06320.29400.050*
H90.81180.72920.37700.073*
H100.96770.72460.54060.074*
H111.16500.84460.58670.071*
H121.19750.97700.47340.066*
H130.81881.14740.08520.048*
H170.43470.94450.42040.063*
H180.52080.82710.28650.063*
H190.66330.88770.13200.056*
H160.48641.12310.39890.060*
H4A0.63620.93740.03700.075*
H4B0.79240.87750.03790.075*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0648 (9)0.0386 (8)0.0391 (8)0.0113 (7)0.0023 (7)0.0000 (6)
O30.0900 (12)0.0412 (9)0.0442 (9)0.0035 (8)0.0052 (8)0.0038 (7)
O20.0702 (10)0.0515 (9)0.0480 (9)0.0175 (7)0.0026 (8)0.0095 (7)
C60.0423 (11)0.0467 (12)0.0360 (11)0.0040 (9)0.0069 (9)0.0015 (9)
C130.0444 (11)0.0347 (10)0.0393 (12)0.0035 (8)0.0046 (9)0.0017 (8)
C140.0383 (10)0.0401 (11)0.0345 (11)0.0039 (8)0.0048 (8)0.0004 (8)
C10.0436 (11)0.0342 (10)0.0361 (11)0.0042 (8)0.0055 (8)0.0019 (8)
C20.0457 (11)0.0409 (11)0.0380 (12)0.0031 (9)0.0081 (9)0.0012 (9)
C50.0415 (10)0.0354 (10)0.0362 (11)0.0020 (8)0.0038 (8)0.0031 (8)
C70.0449 (11)0.0449 (11)0.0388 (12)0.0039 (9)0.0128 (9)0.0039 (9)
C180.0576 (13)0.0480 (13)0.0477 (14)0.0072 (10)0.0040 (10)0.0059 (10)
C80.0519 (12)0.0475 (12)0.0409 (12)0.0038 (9)0.0133 (10)0.0047 (9)
C190.0520 (12)0.0441 (12)0.0401 (12)0.0011 (9)0.0036 (9)0.0023 (9)
C160.0553 (13)0.0567 (14)0.0345 (12)0.0063 (10)0.0010 (9)0.0027 (10)
C40.0520 (12)0.0528 (13)0.0422 (12)0.0112 (10)0.0015 (10)0.0009 (10)
C150.0463 (11)0.0410 (12)0.0365 (11)0.0053 (9)0.0065 (9)0.0017 (9)
C170.0503 (12)0.0646 (15)0.0383 (12)0.0063 (11)0.0013 (9)0.0080 (11)
C90.0690 (16)0.0556 (14)0.0603 (16)0.0072 (12)0.0191 (12)0.0114 (12)
C30.0557 (13)0.0544 (13)0.0492 (14)0.0073 (11)0.0076 (10)0.0049 (10)
C120.0512 (13)0.0651 (14)0.0453 (13)0.0022 (11)0.0038 (10)0.0092 (11)
C110.0614 (14)0.0733 (16)0.0429 (13)0.0160 (13)0.0100 (11)0.0165 (11)
C100.0749 (16)0.0624 (15)0.0524 (15)0.0124 (13)0.0221 (13)0.0224 (12)
Geometric parameters (Å, º) top
O1—C11.232 (2)C18—C171.378 (3)
O3—C151.351 (2)C18—H180.9300
O3—H10.8200C8—C91.383 (3)
O2—C81.372 (2)C19—H190.9300
O2—C31.422 (3)C16—C171.375 (3)
C6—C21.327 (3)C16—C151.387 (3)
C6—C71.446 (3)C16—H160.9300
C6—H60.9300C4—C31.518 (3)
C13—C51.335 (3)C4—H4B0.9700
C13—C141.460 (3)C4—H4A0.9700
C13—H130.9300C17—H170.9300
C14—C151.402 (3)C9—C101.379 (3)
C14—C191.404 (3)C9—H90.9300
C1—C21.464 (3)C3—H30.9800
C1—C51.482 (3)C12—C111.374 (3)
C2—C31.499 (3)C12—H120.9300
C5—C41.514 (3)C11—C101.371 (3)
C7—C121.392 (3)C11—H110.9300
C7—C81.399 (3)C10—H100.9300
C18—C191.370 (3)
C15—O3—H1109.5C17—C16—H16119.9
C8—O2—C3115.33 (16)C15—C16—H16119.9
C2—C6—C7118.87 (18)C5—C4—C3104.63 (16)
C2—C6—H6120.6C5—C4—H4B110.8
C7—C6—H6120.6C3—C4—H4B110.8
C5—C13—C14129.32 (19)C5—C4—H4A110.8
C5—C13—H13115.3C3—C4—H4A110.8
C14—C13—H13115.3H4B—C4—H4A108.9
C15—C14—C19117.62 (17)O3—C15—C16121.96 (18)
C15—C14—C13119.44 (17)O3—C15—C14117.61 (17)
C19—C14—C13122.67 (17)C16—C15—C14120.43 (19)
O1—C1—C2126.76 (18)C16—C17—C18120.6 (2)
O1—C1—C5126.03 (17)C16—C17—H17119.7
C2—C1—C5107.21 (16)C18—C17—H17119.7
C6—C2—C1130.69 (18)C10—C9—C8120.0 (2)
C6—C2—C3120.75 (18)C10—C9—H9120.0
C1—C2—C3108.40 (16)C8—C9—H9120.0
C13—C5—C1121.93 (17)O2—C3—C2113.03 (17)
C13—C5—C4129.92 (17)O2—C3—C4111.83 (18)
C1—C5—C4108.14 (16)C2—C3—C4104.64 (16)
C12—C7—C8118.31 (18)O2—C3—H3109.1
C12—C7—C6123.47 (19)C2—C3—H3109.1
C8—C7—C6118.21 (18)C4—C3—H3109.1
C19—C18—C17119.6 (2)C11—C12—C7121.3 (2)
C19—C18—H18120.2C11—C12—H12119.4
C17—C18—H18120.2C7—C12—H12119.4
O2—C8—C9118.09 (19)C10—C11—C12119.7 (2)
O2—C8—C7121.68 (17)C10—C11—H11120.2
C9—C8—C7120.1 (2)C12—C11—H11120.2
C18—C19—C14121.58 (19)C11—C10—C9120.6 (2)
C18—C19—H19119.2C11—C10—H10119.7
C14—C19—H19119.2C9—C10—H10119.7
C17—C16—C15120.1 (2)
C5—C13—C14—C15162.77 (19)C13—C5—C4—C3160.9 (2)
C5—C13—C14—C1923.4 (3)C1—C5—C4—C318.2 (2)
C7—C6—C2—C1170.40 (19)C17—C16—C15—O3179.13 (19)
C7—C6—C2—C34.5 (3)C17—C16—C15—C140.9 (3)
O1—C1—C2—C618.8 (3)C19—C14—C15—O3179.75 (17)
C5—C1—C2—C6161.6 (2)C13—C14—C15—O36.1 (3)
O1—C1—C2—C3165.79 (19)C19—C14—C15—C160.3 (3)
C5—C1—C2—C313.7 (2)C13—C14—C15—C16173.86 (18)
C14—C13—C5—C1175.45 (17)C15—C16—C17—C181.4 (3)
C14—C13—C5—C45.6 (3)C19—C18—C17—C160.7 (3)
O1—C1—C5—C133.4 (3)O2—C8—C9—C10175.76 (19)
C2—C1—C5—C13176.08 (17)C7—C8—C9—C100.4 (3)
O1—C1—C5—C4177.37 (19)C8—O2—C3—C240.8 (2)
C2—C1—C5—C43.1 (2)C8—O2—C3—C4158.55 (16)
C2—C6—C7—C12172.63 (19)C6—C2—C3—O229.1 (3)
C2—C6—C7—C88.3 (3)C1—C2—C3—O2146.85 (17)
C3—O2—C8—C9153.34 (19)C6—C2—C3—C4151.0 (2)
C3—O2—C8—C730.5 (3)C1—C2—C3—C424.9 (2)
C12—C7—C8—O2174.15 (18)C5—C4—C3—O2148.59 (17)
C6—C7—C8—O24.9 (3)C5—C4—C3—C225.9 (2)
C12—C7—C8—C91.9 (3)C8—C7—C12—C111.4 (3)
C6—C7—C8—C9179.01 (18)C6—C7—C12—C11179.62 (19)
C17—C18—C19—C140.5 (3)C7—C12—C11—C100.7 (3)
C15—C14—C19—C180.9 (3)C12—C11—C10—C92.2 (4)
C13—C14—C19—C18172.99 (19)C8—C9—C10—C111.7 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C13—H13···O30.932.422.750 (2)101
C13—H13···O10.932.592.917 (2)102
O3—H1···O1i0.821.932.749 (2)178
C3—H3···Cg1ii0.982.853.746 (2)152
C6—H6···Cg1iii0.932.923.476 (2)120
C12—H12···Cg2iv0.933.253.471 (2)96
Symmetry codes: (i) x1/2, y+5/2, z1/2; (ii) x+1, y+2, z; (iii) x+2, y+2, z; (iv) x+2, y+2, z+1.

Experimental details

(I)(II)
Crystal data
Chemical formulaC12H10O2C19H14O3
Mr186.20290.30
Crystal system, space groupMonoclinic, P21/nMonoclinic, P21/n
Temperature (K)298298
a, b, c (Å)5.8015 (14), 7.6260 (19), 20.661 (5)8.8978 (9), 12.5893 (12), 13.1797 (13)
β (°) 91.254 (3) 102.157 (2)
V3)913.9 (4)1443.2 (2)
Z44
Radiation typeMo KαMo Kα
µ (mm1)0.090.09
Crystal size (mm)0.73 × 0.25 × 0.250.36 × 0.23 × 0.23
Data collection
DiffractometerBruker SMART CCD area-detector
diffractometer
Bruker SMART CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Multi-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.723, 0.9780.733, 0.980
No. of measured, independent and
observed [I > 2 σ(I)] reflections
4188, 1579, 1324 5951, 2543, 1881
Rint0.0160.056
(sin θ/λ)max1)0.5950.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.046, 0.126, 1.04 0.051, 0.135, 1.00
No. of reflections15792543
No. of parameters137200
No. of restraints30
H-atom treatmentH-atom parameters constrainedH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.24, 0.220.43, 0.17

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 2000), SHELXTL.

Selected geometric parameters (Å, º) for (I) top
O2—C3A1.408 (3)C2—C3A1.544 (3)
O2—C31.415 (3)C3—C41.493 (3)
C2—C61.312 (2)C3A—C41.490 (3)
C2—C31.534 (3)
C6—C2—C1132.68 (16)C2—C6—C7119.51 (15)
C6—C2—C3—O240.2 (3)C6—C2—C3A—O243.2 (3)
C1—C2—C3—O2152.68 (18)C1—C2—C3A—O2156.04 (19)
Selected geometric parameters (Å, º) for (II) top
O2—C81.372 (2)C6—C71.446 (3)
O2—C31.422 (3)C13—C51.335 (3)
C6—C21.327 (3)C13—C141.460 (3)
C2—C6—C7118.87 (18)C13—C5—C1121.93 (17)
C5—C13—C14129.32 (19)C13—C5—C4129.92 (17)
C6—C2—C1130.69 (18)
C5—C13—C14—C1923.4 (3)C1—C2—C3—O2146.85 (17)
C14—C13—C5—C45.6 (3)C6—C2—C3—C4151.0 (2)
Hydrogen-bond geometry (Å, º) for (II) top
D—H···AD—HH···AD···AD—H···A
C13—H13···O30.932.422.750 (2)101
C13—H13···O10.932.592.917 (2)102
O3—H1···O1i0.821.932.749 (2)178
C3—H3···Cg1ii0.982.853.746 (2)152
C6—H6···Cg1iii0.932.923.476 (2)120
C12—H12···Cg2iv0.933.253.471 (2)96
Symmetry codes: (i) x1/2, y+5/2, z1/2; (ii) x+1, y+2, z; (iii) x+2, y+2, z; (iv) x+2, y+2, z+1.
 

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