Buy article online - an online subscription or single-article purchase is required to access this article.
Download citation
Download citation
link to html
Two polymorphs of 20-desmethyl-β-carotene (systematic name: 20-nor-β,β-carotene), C39H54, in monoclinic and triclinic space groups, were formed in the same vial by recrystallization from pyridine and water. Each polymorph crystallizes with the complete mol­ecule as the asymmetric unit, and the two polymorphs show differing patterns of disorder. The β end rings of both polymorphs have the 6-s-cis conformation, and are twisted out of the plane of the polyene chain by angles of −53.2 (8) and 47.3 (8)° for the monoclinic polymorph, and −43.6 (3) and 56.1 (3)° for the triclinic polymorph. The cyclo­hexene end groups are in the half-chair conformation, but the triclinic polymorph shows disorder of one ring. Overlay of the mol­ecules shows that they differ in the degree of nonplanarity of the polyene chains and the angles of twist of the end rings. The packing arrangements of the two polymorphs are quite different, with the monoclinic polymorph showing short inter­molecular contacts of the disordered methyl groups with adjacent polyene chain atoms, and the triclinic polymorph showing π–π stacking inter­actions of the almost parallel polyene chains. The determination of the crystal structures of the two title polymorphs of 20-desmethyl-β-carotene allows information to be gained regarding the structural effects on the polyene chain, as well as on the end groups, versus that of the parent compound β-carotene. The absence of the methyl group is known to have an impact on various functions of the title compound.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270108007816/jz3128sup1.cif
Contains datablocks I-P21, I-P-1, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270108007816/jz3128I-P21sup2.hkl
Contains datablock I-P21

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270108007816/jz3128I-P-1sup3.hkl
Contains datablock I-P-1

CCDC references: 690186; 690187

Comment top

The isoprenoid structure with methyl groups in positions 19, 20, 19' and 20' of the polyene chain in carotenoids is a consequence of the biosynthetic pathway (Britton, 1998). These methyl groups cause a bathochromic shift of the absorption spectrum in visible light relative to unsubstituted aryl polyenes (Zechmeister, 1963). The in-chain methyl substituents facilitate NMR assignments of the polyene chain (Englert, 1995). Norcarotenoids lacking lateral methyl groups have been prepared as models by total synthesis (Britton et al., 1997; Weesie et al., 1999; Martin et al., 1999; Wirtz et al., 2001), and are particularly useful for assessing the specificity of the C20 cleavage enzyme (Wirtz et al., 2001), Raman spectroscopic studies (Weesie et al., 1999) and antioxidant properties (Martin et al., 1999), and for carotenoprotein binding (Britton et al., 1998 [Should this be Britton, 1998 ?]). It has been demonstrated that the 20-methyl group is essential for recombination of the colourless apocrustacyanin with carotenoids to provide blue carotenoproteins (Britton et al., 1998), and recent X-ray studies of β-crustacyanin provide a three-dimensional structural basis to rationalize the previous findings (Cianci et al. 2002). Here, we report the crystal structures of two polymorphs of 20-desmethyl-β-carotene, (I), formed in the same recrystallization vial, which crystallize in the monoclinic space group P21 and the triclinic space group P1, and which we thus refer to as (I)-P21 and (I)-P1, respectively.

In the scheme of 20-desmethyl-β-carotene, the numbering of the C atoms is indicated according to IUPAC nomenclature rules (IUPAC–IUB, 1974). However, in the crystal structures, primed positions are denoted with the suffix A for clarity, e.g. C13' = C13A. The structures of the two polymorphs are shown in Figs. 1 and 2, respectively, with disordered atoms omitted in Fig. 1(a). Each crystal structure shows disorder of the C13 and C20 sites with those on the other half of the molecule, C13A and C20A (Figs. 1b and 2). The proportions of the disordered components are quite different. For (I)—P21, the value is 1:1, but for (I)—P1, the highest occupancy fraction refines to a value of 0.821 (4). The (I)—P1 polymorph shows additional disorder of atoms C2A, C3A and C16A of one cyclohexene ring, with the refined occupancy of the major component being 0.542 (9) (Fig. 2).

In common with β-carotene and other all-trans C40 carotenoids (Mo, 1995, Bartalucci et al., 2007), in each polymorph of 1, the polyene chain methyl groups of each half of the molecule are arranged on opposite sides of the chain, and there is a pronounced S shape of the polyene chain, to minimize steric hindrance, Figs 1 and 2. Overall the conformations of the two polymorphs are fairly similar to one another and to that of β-carotene [Senge et al., 1992; Cambridge Structural Database (CSD; Allen, 2002) refcode CARTEN01], with end groups in the 6 − s-cis conformation (Mo, 1995; Bartalucci et al., 2008). These are twisted out of the plane of the polyene chain by angles defined by the C5—C6—C7—C8 and C5A—C6A—C7A—C8A torsion angles which describes the non-planarity between the best planes through the double bond systems of the ring and the polyene chain (Sundaralingam & Beddell, 1972; Mo, 1995; Bartalucci et al., 2008); these angles are −53.2 (8) and 47.3 (8) ° for (I)—P21 and −43.6 (3) and 56.1 (3)° for (I)—P1 (Table 1), compared with a value of ±41.6 (6) ° for the centrosymmetric β-carotene molecule (Senge et al., 1992; CSD refcode CARTEN01). These values are in reasonable agreement with the calculated value for β-carotene of 48.0° (Hashimoto et al. 2002), since such a twist of the end ring minimizes steric hindrance between the H atoms bonded to atoms C7 and C8 and those of the end ring methyl H atoms, and therefore is the most stable conformer.

The cyclohexene end rings are all in the usual half-chair conformation and are well ordered except for one ring of (I)—P1. This shows disorder of atoms C2A, C3A and C16A (Fig. 3), similar to that shown by, for example, β-carotene and canthaxanthin (Senge et al., 1992; Bartalucci et al., 2007), indicating that both possible half-chair conformations are present. In the half-chair conformation, atoms C1 and C4–C6 (C1A and C4A–C6A) are approximately coplanar, with atoms C2 and C3 (C2A and C3A) lying above and below this plane. For (I)—P21, the distances of atoms C2 and C3 (C2A and C3A) from the C1/C4–C6 (C1A/C4A–C6A) planes are 0.370 (5) and −0.409 (6) Å [−0.231 (5) and 0.516 (5) Å], respectively, and the angle between the C1/C4–C6 and C1A/C4A–C6A planes is 24.3 (3)°. For (I)—P1, the distances from the corresponding planes are 0.343 (2) and −0.412 (3) Å [−0.466 (8) and 0.347 (7) Å for atoms C2A and C3A, and 0.476 (8) and −0.300 (8) Å, for atoms C2B and C3B, from the C1A/C4A–C6A plane], and the angle between the end ring planes is 22.8 (1)°. The torsion angles about the end rings of each polymorph (Table 1) display the normal features expected for a half-chair conformation. In particular, the largest torsion angle is about the C2—C3 bond, with values in the range 61.8 (5)–66.5 (8)°. The smallest values are expected to be about the C5C6 double bond, which they are within experimental error, in the range 2.3 (9)–8.3 (3)°.

The polyene chains in both polymorphs are significantly non-planar, shown by the torsion angles along the polyene chains, as is normally the case (Mo, 1995; Bartalucci, 2008). The largest deviations from 180° are C11—C12—C13—C14 = −172.6 (5)° for (I)—P21, and C8A—C9A—C10A—C11A = −173.3 (2)° for (I)—P1, and the torsion angles for both polymorphs show less deviation from 180° towards the centre of the molecule, and for one half of the molecule versus the other. The latter trend is also reflected in the deviation of the methyl group torsion angles along the polyene chains, with largest values of C11—C12—C13—C20 = −13.5 (10)° for (I)—P21 and C20A—C13A—C14A—C15A = 12.0 (6)° for (I)—P1. The greatest deviations of the methyl groups from the plane of the polyene chain are −0.735 (6) Å for atom C19 in (I)—P21 and 0.363 (2) Å for atom C19A in (I)—P1.

A detailed comparison of the two polymorphs has been carried out by overlaying the structures using the program OFIT from the SHELXTL package (Bruker, 2001). Firstly, an overlay of atoms C1 and C4–C6 of the C1–C6 end rings of (I)—P21 and (I)—P1 clearly shows that these rings are very similar, and in the same half-chair conformation (with the selected absolute configuration) (Fig. 4). A similar overlay of atoms C1A and C4A–C6A of the C1A–C6A end rings shows that the A component of the disordered end ring of (I)—P1 fits reasonably closely, illustrating that the B component has the alternative half-chair conformation (Fig. 5). An overlay of the polyene chain atoms of each polymorph shows that they are reasonably similar, with an r.m.s. deviation of 0.22 Å. Looking down on the plane of the polyene chain, the chains appear to fit very well (Fig. 6a), but the differences leading to the r.m.s. deviation of 0.22 Å are much more apparent when the overlay is viewed down the plane of the polyene chain of (I)—P1, reflecting the differences in torsion angles along the polyene chain for the two polymorphs (Fig. 6b). When the end ring atoms are included in the fit (excluding atoms C2B and C3B and the methyl groups), the r.m.s. deviation doubles to 0.44 Å, due to both the differing tilt angles of the end rings and the differing deviations from planarity of the polyene chains (Fig. 6).

In the (I)—P21 polymorph, there is no indication of the π-stacking interactions between polyene chains which have been seen in a number of related carotenoids (Bartalucci et al., 2007, 2008). However, there are some short contacts between the half-occupancy atoms C20 and C20A and atoms of adjacent polyene chains. The shortest contacts are C20···C15A(1 − x, −1/2 + y, −z) and C20A···C14A(−x, 1/2 + y, −z), with distances of 3.01 (1) and 3.07 (2) Å, respectively (Fig. 7a). For (I)—P1, the shortest contacts again involve the partially occupied atoms C20 and C20A [occupancies 0.821 (4) and 0.179 (4)], with distances of 3.444 (3) and 3.34 (1) Å for C20···C14(−x, −y + 1, −z + 1) and C20A···C10A(−x + 1, −y + 2, −z + 2), respectively (Fig. 7b). The polyene chains lie one above the other with possible π-stacking interactions of the almost parallel polyene chains, with a minimum distance for C13···C15(−x, −y + 1, −z + 1) of 3.687 (3) Å. Overall, the packing arrangements of the two polymorphs are of course quite different, by virtue of the different space group symmetries (Fig. 8).

In summary, the two polymorphs of 20-desmethyl-β-carotene, (I), show differences in their patterns of disorder and conformations, as well as having quite different packing arrangements.

Experimental top

For the present work, synthetic 20-desmethyl-β-carotene, (I), (Wirtz et al., 2001) was available, and thus offered information on the structural effect on the polyene chain for an intact 20-norcarotene.

The two different polymorphs of 20-desmethyl-β-carotene, (I), were crystallized in the same vial, using a vapour diffusion technique with water diffused into a solution of (I) in pyridine, with the solvents in an arbitrary ratio.

Refinement top

Polymorphs (I)—P21 and (I)—P1 both showed disorder between the two halves of the molecule, arising from the absence of the 20-methyl group bonded to C13 (or C13A). In (I)—P21, the occupancy of C20 refined to a value of 0.498 (8), and so the C20/C20A components were fixed at 0.5 for the final rounds of refinement. For (I)—P1, the final refined occupancy of C20 (versus C20A) was 0.821 (4). (I)—P1 showed additional disorder of atoms C2A, C3A and C16A, arising from the presence of both half-chair conformations of the cyclohexene ring. The final refined occupancy of the major component was 0.542 (9). Some restraints were applied to the geometry of the disordered atoms of (I)—P1: in the disordered end ring, equivalent bond distances of the two components were restrained to be the same using the SAME command (SHELXL97; Sheldrick, 2008), and the C13A—C20A distance was restrained to be 1.5 Å.

In both structures, H atoms were included in calculated positions, with C—H distances varying from 0.95 to 0.99 Å and with Uiso values of 1.2 or 1.5 times Ueq of the parent C atom. Methyl H atoms were defined using the AFIX 137 command (SHELXL97; Sheldrick, 2008), which varies the torsion angle to maximize the electron density at the three H-atom positions.

Computing details top

For both compounds, data collection: SMART (Bruker, 2001); cell refinement: SMART (Bruker, 2001). Data reduction: SMART (Bruker, 2001) for I-P21; SAINT (Bruker, 2002) for I-P-1. For both compounds, program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Bruker, 2001); software used to prepare material for publication: SHELXTL (Bruker, 2001).

Figures top
[Figure 1] Fig. 1. (a) The molecular structure of (I)—P21, showing the atom-numbering scheme adopted for both polymorphs. Displacement ellipsoids are drawn at the 50% probability level and H atoms are shown as small spheres of arbitrary radii. Disordered atoms have been omitted for clarity. (b) The disorder of atoms C20 and C20A, which each have an occupancy of 0.5; the second component is shown with an open bond. H atoms have been omitted for clarity.
[Figure 2] Fig. 2. The molecular structure of (I)—P1, with displacement ellipsoids drawn at the 50% probability level, showing the disorder of atoms C20 and C20A, and atoms C2A/C3A/C16A and C2B/C3B/C16B. The major and minor components are represented with solid and open bonds, respectively. H atoms have been omitted for clarity.
[Figure 3] Fig. 3. The disordered end ring of (I)—P1. The refined occupancy of the A component, shown with solid bonds, is 0.542 (9).
[Figure 4] Fig. 4. Overlay of atoms C1/C4–C6 of the C1–C6 end rings of the two polymorphs, showing their similarity, with the (I)—P21 polymorph represented with dashed lines.
[Figure 5] Fig. 5. Overlay of atoms C1A/C4A–C6A of the C1A–C6A end rings of the two polymorphs. The A component of the disordered (I)—P1 polymorph is represented with shaded atoms and solid bonds, and the B component with shaded atoms and open bonds. The (I)—P21 polymorph is represented with dashed atoms and bonds.
[Figure 6] Fig. 6. Overlays of the polyene chains of the two polymorphs, (a) viewed face on to the plane of the polyene chain, and (b) viewed down the plane of the polyene chain of (I)—P1. The (I)—P21 polymorph is represented with dashed lines.
[Figure 7] Fig. 7. Intermolecular interactions of the polymorphs. (a) (I)—P21 [symmetry codes: 1555.01 (x, y, z); 2645.O1 (1 − x, −1/2 + y, −z); 2555.O1 (−x, 1/2 + y, −z); 2655.O1 (1 − x, 1/2 + y, −z); 2545.O1 (−x, −1/2 + y, 1 − z)]. (b) (I)—P1 [symmetry codes: 1555.O1 (x, y, z); 2677.O1 (1 − x, 2 − y, 2 − z); 2566.O1 (−x, 1 − y, −z)].
[Figure 8] Fig. 8. Packing diagrams for (a) (I)—P21 and (b) (I)—P1, viewed in each case down the a axis.
(I-P21) 20-nor-β,β-carotene top
Crystal data top
C39H54F(000) = 576
Mr = 522.82Dx = 1.038 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P2ybCell parameters from 879 reflections
a = 9.442 (2) Åθ = 2.2–23.4°
b = 7.6914 (16) ŵ = 0.06 mm1
c = 23.090 (5) ÅT = 100 K
β = 93.733 (3)°Plate, orange
V = 1673.3 (6) Å30.40 × 0.22 × 0.05 mm
Z = 2
Data collection top
Bruker SMART CCD area-detector
diffractometer
1530 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.085
Graphite monochromatorθmax = 25.0°, θmin = 1.8°
ϕ and ω scansh = 1111
8554 measured reflectionsk = 96
3196 independent reflectionsl = 2724
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.058H-atom parameters constrained
wR(F2) = 0.112 w = 1/[σ2(Fo2) + (0.0379P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.85(Δ/σ)max < 0.001
3195 reflectionsΔρmax = 0.15 e Å3
373 parametersΔρmin = 0.15 e Å3
1 restraintExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0090 (11)
Crystal data top
C39H54V = 1673.3 (6) Å3
Mr = 522.82Z = 2
Monoclinic, P21Mo Kα radiation
a = 9.442 (2) ŵ = 0.06 mm1
b = 7.6914 (16) ÅT = 100 K
c = 23.090 (5) Å0.40 × 0.22 × 0.05 mm
β = 93.733 (3)°
Data collection top
Bruker SMART CCD area-detector
diffractometer
1530 reflections with I > 2σ(I)
8554 measured reflectionsRint = 0.085
3196 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0581 restraint
wR(F2) = 0.112H-atom parameters constrained
S = 0.85Δρmax = 0.15 e Å3
3195 reflectionsΔρmin = 0.15 e Å3
373 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)
C11.2631 (5)0.8976 (7)0.4236 (2)0.0352 (14)
C21.3194 (6)0.9956 (7)0.4784 (2)0.0498 (18)
H2A1.31200.91960.51260.060*
H2B1.42091.02350.47510.060*
C31.2382 (6)1.1621 (7)0.4872 (2)0.0515 (17)
H3A1.27201.21730.52430.062*
H3B1.13571.13650.48870.062*
C41.2619 (5)1.2840 (7)0.43679 (19)0.0432 (16)
H4A1.35851.33410.44200.052*
H4B1.19311.38100.43720.052*
C51.2456 (5)1.1928 (8)0.3779 (2)0.0340 (15)
C61.2409 (5)1.0230 (8)0.3725 (2)0.0331 (15)
C71.2107 (5)0.9344 (8)0.3151 (2)0.0387 (15)
H71.27590.84880.30390.046*
C81.0987 (5)0.9679 (7)0.2791 (2)0.0309 (13)
H81.03801.05890.29020.037*
C91.0589 (6)0.8809 (7)0.2249 (2)0.0364 (15)
C100.9338 (5)0.9239 (8)0.1972 (2)0.0386 (15)
H100.88431.01570.21460.046*
C110.8639 (5)0.8532 (7)0.1456 (2)0.0408 (16)
H110.91170.76730.12460.049*
C120.7330 (5)0.9032 (7)0.1255 (2)0.0420 (16)
H120.69290.99820.14500.050*
C130.6466 (6)0.8295 (8)0.0777 (2)0.0407 (16)
H130.68580.74370.05380.049*0.42 (6)
C140.5128 (6)0.8804 (8)0.0667 (2)0.0465 (17)
H140.47890.97040.09040.056*
C150.4147 (6)0.8108 (9)0.0220 (2)0.062 (2)
H150.44780.72220.00240.075*
C161.3780 (5)0.7607 (7)0.4123 (2)0.0483 (16)
H16D1.40550.69920.44850.072*
H16E1.46130.81890.39800.072*
H16F1.34020.67730.38320.072*
C171.1263 (5)0.8026 (7)0.4338 (2)0.0450 (16)
H17D1.14400.71580.46440.068*
H17E1.09130.74450.39790.068*
H17F1.05520.88610.44550.068*
C181.2359 (5)1.3246 (7)0.32914 (19)0.0381 (15)
H18A1.23111.26390.29180.057*
H18B1.32001.39960.33210.057*
H18C1.15051.39570.33200.057*
C191.1552 (5)0.7397 (8)0.2040 (2)0.0558 (18)
H19A1.12150.70340.16480.084*
H19B1.15420.63980.23030.084*
H19C1.25220.78460.20330.084*
C200.7140 (11)0.7184 (16)0.0416 (5)0.051 (4)0.50
H20A0.65010.69070.00770.077*0.50
H20B0.74000.61110.06250.077*0.50
H20C0.79980.77440.02880.077*0.50
C1A0.7527 (5)0.8309 (7)0.3307 (2)0.0355 (15)
C2A0.8418 (5)0.7506 (7)0.3815 (2)0.0357 (14)
H2C0.93370.71180.36760.043*
H2D0.86180.84060.41150.043*
C3A0.7699 (5)0.5980 (8)0.4084 (2)0.0433 (15)
H3C0.67760.63470.42230.052*
H3D0.82990.55350.44190.052*
C4A0.7469 (5)0.4551 (8)0.3624 (2)0.0419 (15)
H4C0.83950.40260.35480.050*
H4D0.68630.36270.37760.050*
C5A0.6774 (5)0.5247 (8)0.3062 (2)0.0373 (15)
C6A0.6775 (5)0.6913 (7)0.2923 (2)0.0313 (14)
C7A0.6060 (5)0.7632 (7)0.2379 (2)0.0349 (14)
H7A0.65920.84190.21620.042*
C8A0.4733 (5)0.7269 (7)0.2167 (2)0.0328 (14)
H8A0.42170.64280.23690.039*
C9A0.4030 (5)0.8051 (7)0.1659 (2)0.0346 (15)
C10A0.2658 (5)0.7673 (7)0.1514 (2)0.0377 (15)
H10A0.22210.68570.17550.045*
C11A0.1786 (6)0.8365 (8)0.1037 (2)0.0548 (19)
H11A0.21950.91970.07940.066*
C12A0.0423 (6)0.7910 (9)0.0913 (3)0.072 (2)
H12A0.00270.70800.11610.087*
C13A0.0487 (7)0.8564 (10)0.0439 (3)0.082 (3)
H13A0.01250.94300.01950.099*0.58 (6)
C14A0.1829 (7)0.8008 (10)0.0325 (3)0.083 (3)
H14A0.21620.71180.05670.100*
C15A0.2797 (7)0.8637 (10)0.0129 (3)0.086 (3)
H15A0.24600.94900.03840.103*
C16A0.6384 (5)0.9487 (8)0.3548 (2)0.0409 (15)
H16A0.68421.04400.37700.061*
H16B0.58020.88050.38010.061*
H16C0.57800.99650.32250.061*
C17A0.8508 (5)0.9444 (7)0.2955 (2)0.0404 (15)
H17A0.92130.87050.27830.061*
H17B0.89931.03000.32130.061*
H17C0.79411.00500.26470.061*
C18A0.6109 (5)0.3801 (7)0.2692 (2)0.0403 (16)
H18D0.58190.42530.23060.060*
H18E0.52760.33490.28750.060*
H18F0.68010.28630.26570.060*
C19A0.4865 (5)0.9361 (8)0.1331 (2)0.0542 (18)
H19D0.51101.03560.15830.081*
H19E0.42880.97590.09880.081*
H19F0.57350.88170.12090.081*
C20A0.0150 (13)0.9857 (19)0.0073 (6)0.084 (6)0.50
H20D0.01961.09800.02740.126*0.50
H20E0.04280.99720.02930.126*0.50
H20F0.11110.94860.00070.126*0.50
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.029 (3)0.035 (4)0.042 (3)0.002 (3)0.004 (3)0.001 (3)
C20.052 (4)0.052 (5)0.043 (4)0.001 (3)0.017 (3)0.001 (3)
C30.078 (4)0.043 (4)0.031 (3)0.002 (4)0.012 (3)0.006 (3)
C40.044 (3)0.043 (4)0.040 (3)0.005 (3)0.013 (3)0.010 (3)
C50.031 (3)0.034 (4)0.036 (3)0.000 (3)0.010 (3)0.004 (3)
C60.024 (3)0.052 (5)0.023 (3)0.001 (3)0.002 (3)0.003 (3)
C70.031 (3)0.045 (4)0.039 (3)0.004 (3)0.004 (3)0.006 (3)
C80.033 (3)0.028 (4)0.032 (3)0.001 (3)0.001 (3)0.002 (3)
C90.047 (3)0.033 (4)0.028 (3)0.001 (3)0.002 (3)0.009 (3)
C100.049 (3)0.035 (4)0.031 (3)0.007 (3)0.006 (3)0.010 (3)
C110.043 (3)0.038 (4)0.040 (3)0.002 (3)0.007 (3)0.002 (3)
C120.051 (4)0.036 (4)0.037 (3)0.019 (3)0.007 (3)0.003 (3)
C130.037 (3)0.050 (5)0.034 (3)0.002 (3)0.006 (3)0.003 (3)
C140.057 (4)0.050 (5)0.031 (3)0.009 (4)0.013 (3)0.002 (3)
C150.058 (4)0.078 (6)0.048 (4)0.003 (4)0.019 (3)0.014 (4)
C160.046 (3)0.044 (4)0.054 (4)0.011 (3)0.007 (3)0.003 (3)
C170.038 (3)0.039 (4)0.057 (4)0.001 (3)0.010 (3)0.017 (3)
C180.032 (3)0.045 (4)0.037 (3)0.005 (3)0.004 (3)0.005 (3)
C190.053 (4)0.067 (5)0.045 (4)0.002 (4)0.016 (3)0.026 (4)
C200.041 (7)0.065 (10)0.044 (7)0.003 (7)0.022 (6)0.004 (7)
C1A0.030 (3)0.040 (4)0.036 (3)0.010 (3)0.004 (3)0.001 (3)
C2A0.030 (3)0.040 (4)0.036 (3)0.005 (3)0.003 (3)0.001 (3)
C3A0.035 (3)0.055 (4)0.039 (3)0.003 (3)0.007 (3)0.013 (4)
C4A0.036 (3)0.044 (4)0.044 (4)0.000 (3)0.010 (3)0.006 (3)
C5A0.031 (3)0.048 (5)0.032 (3)0.000 (3)0.008 (3)0.005 (3)
C6A0.024 (3)0.027 (4)0.042 (4)0.004 (3)0.007 (3)0.008 (3)
C7A0.038 (3)0.031 (4)0.035 (3)0.003 (3)0.001 (3)0.004 (3)
C8A0.035 (3)0.027 (4)0.036 (3)0.000 (3)0.003 (3)0.002 (3)
C9A0.042 (3)0.034 (4)0.027 (3)0.002 (3)0.000 (3)0.002 (3)
C10A0.045 (3)0.035 (4)0.032 (3)0.007 (3)0.006 (3)0.007 (3)
C11A0.052 (4)0.062 (5)0.048 (4)0.006 (4)0.012 (3)0.009 (4)
C12A0.056 (4)0.095 (6)0.061 (4)0.025 (5)0.025 (4)0.033 (4)
C13A0.061 (5)0.101 (7)0.081 (5)0.019 (4)0.020 (4)0.060 (5)
C14A0.052 (4)0.121 (7)0.071 (4)0.027 (5)0.034 (4)0.050 (5)
C15A0.066 (5)0.111 (7)0.077 (5)0.020 (5)0.033 (4)0.051 (5)
C16A0.037 (3)0.044 (4)0.041 (3)0.003 (3)0.006 (3)0.002 (3)
C17A0.037 (3)0.029 (4)0.053 (4)0.003 (3)0.006 (3)0.001 (3)
C18A0.035 (3)0.040 (4)0.045 (3)0.002 (3)0.009 (3)0.003 (3)
C19A0.051 (4)0.062 (5)0.046 (4)0.010 (4)0.020 (3)0.025 (3)
C20A0.047 (8)0.091 (13)0.110 (12)0.008 (8)0.031 (8)0.077 (10)
Geometric parameters (Å, º) top
C1—C171.515 (7)C1A—C2A1.527 (6)
C1—C61.529 (7)C1A—C6A1.537 (7)
C1—C21.537 (7)C1A—C16A1.540 (7)
C1—C161.547 (7)C1A—C17A1.543 (7)
C2—C31.513 (7)C2A—C3A1.510 (7)
C2—H2A0.9900C2A—H2C0.9900
C2—H2B0.9900C2A—H2D0.9900
C3—C41.523 (7)C3A—C4A1.533 (7)
C3—H3A0.9900C3A—H3C0.9900
C3—H3B0.9900C3A—H3D0.9900
C4—C51.529 (6)C4A—C5A1.515 (6)
C4—H4A0.9900C4A—H4C0.9900
C4—H4B0.9900C4A—H4D0.9900
C5—C61.313 (6)C5A—C6A1.321 (7)
C5—C181.513 (7)C5A—C18A1.513 (7)
C6—C71.499 (7)C6A—C7A1.493 (6)
C7—C81.327 (6)C7A—C8A1.344 (5)
C7—H70.9500C7A—H7A0.9500
C8—C91.448 (6)C8A—C9A1.440 (6)
C8—H80.9500C8A—H8A0.9500
C9—C101.348 (6)C9A—C10A1.349 (6)
C9—C191.516 (7)C9A—C19A1.513 (7)
C10—C111.432 (6)C10A—C11A1.434 (6)
C10—H100.9500C10A—H10A0.9500
C11—C121.347 (6)C11A—C12A1.346 (6)
C11—H110.9500C11A—H11A0.9500
C12—C131.444 (6)C12A—C13A1.437 (7)
C12—H120.9500C12A—H12A0.9500
C13—C141.331 (6)C13A—C14A1.348 (7)
C13—C201.379 (13)C13A—C20A1.460 (14)
C13—H130.9500C13A—H13A0.9500
C14—C151.445 (6)C14A—C15A1.429 (7)
C14—H140.9500C14A—H14A0.9500
C15—C15A1.342 (7)C15A—H15A0.9500
C15—H150.9500C16A—H16A0.9800
C16—H16D0.9800C16A—H16B0.9800
C16—H16E0.9800C16A—H16C0.9800
C16—H16F0.9800C17A—H17A0.9800
C17—H17D0.9800C17A—H17B0.9800
C17—H17E0.9800C17A—H17C0.9800
C17—H17F0.9800C18A—H18D0.9800
C18—H18A0.9800C18A—H18E0.9800
C18—H18B0.9800C18A—H18F0.9800
C18—H18C0.9800C19A—H19D0.9800
C19—H19A0.9800C19A—H19E0.9800
C19—H19B0.9800C19A—H19F0.9800
C19—H19C0.9800C20A—H20D0.9800
C20—H20A0.9800C20A—H20E0.9800
C20—H20B0.9800C20A—H20F0.9800
C20—H20C0.9800
C17—C1—C6110.4 (4)C6A—C1A—C16A108.1 (4)
C17—C1—C2111.3 (5)C2A—C1A—C17A108.3 (4)
C6—C1—C2110.4 (4)C6A—C1A—C17A111.2 (4)
C17—C1—C16108.2 (4)C16A—C1A—C17A108.4 (4)
C6—C1—C16111.1 (4)C3A—C2A—C1A113.0 (4)
C2—C1—C16105.3 (4)C3A—C2A—H2C109.0
C3—C2—C1112.0 (4)C1A—C2A—H2C109.0
C3—C2—H2A109.2C3A—C2A—H2D109.0
C1—C2—H2A109.2C1A—C2A—H2D109.0
C3—C2—H2B109.2H2C—C2A—H2D107.8
C1—C2—H2B109.2C2A—C3A—C4A108.6 (4)
H2A—C2—H2B107.9C2A—C3A—H3C110.0
C2—C3—C4108.5 (5)C4A—C3A—H3C110.0
C2—C3—H3A110.0C2A—C3A—H3D110.0
C4—C3—H3A110.0C4A—C3A—H3D110.0
C2—C3—H3B110.0H3C—C3A—H3D108.3
C4—C3—H3B110.0C5A—C4A—C3A112.0 (5)
H3A—C3—H3B108.4C5A—C4A—H4C109.2
C3—C4—C5112.7 (4)C3A—C4A—H4C109.2
C3—C4—H4A109.1C5A—C4A—H4D109.2
C5—C4—H4A109.1C3A—C4A—H4D109.2
C3—C4—H4B109.1H4C—C4A—H4D107.9
C5—C4—H4B109.1C6A—C5A—C18A125.7 (5)
H4A—C4—H4B107.8C6A—C5A—C4A122.9 (5)
C6—C5—C18126.5 (5)C18A—C5A—C4A111.4 (5)
C6—C5—C4122.8 (5)C5A—C6A—C7A123.8 (5)
C18—C5—C4110.6 (5)C5A—C6A—C1A123.0 (5)
C5—C6—C7122.7 (5)C7A—C6A—C1A113.2 (5)
C5—C6—C1123.5 (5)C8A—C7A—C6A126.1 (5)
C7—C6—C1113.8 (5)C8A—C7A—H7A117.0
C8—C7—C6124.3 (5)C6A—C7A—H7A117.0
C8—C7—H7117.9C7A—C8A—C9A125.3 (5)
C6—C7—H7117.9C7A—C8A—H8A117.3
C7—C8—C9127.1 (5)C9A—C8A—H8A117.3
C7—C8—H8116.4C10A—C9A—C8A119.8 (5)
C9—C8—H8116.4C10A—C9A—C19A122.8 (5)
C10—C9—C8117.9 (5)C8A—C9A—C19A117.3 (4)
C10—C9—C19123.4 (5)C9A—C10A—C11A127.2 (5)
C8—C9—C19118.7 (4)C9A—C10A—H10A116.4
C9—C10—C11130.1 (6)C11A—C10A—H10A116.4
C9—C10—H10114.9C12A—C11A—C10A124.1 (6)
C11—C10—H10114.9C12A—C11A—H11A117.9
C12—C11—C10122.7 (6)C10A—C11A—H11A117.9
C12—C11—H11118.6C11A—C12A—C13A126.0 (6)
C10—C11—H11118.6C11A—C12A—H12A117.0
C11—C12—C13127.6 (6)C13A—C12A—H12A117.0
C11—C12—H12116.2C14A—C13A—C12A123.1 (6)
C13—C12—H12116.2C14A—C13A—C20A121.4 (7)
C14—C13—C20122.5 (6)C12A—C13A—C20A115.5 (7)
C14—C13—C12120.8 (6)C14A—C13A—H13A118.4
C20—C13—C12116.5 (6)C12A—C13A—H13A118.4
C14—C13—H13119.6C13A—C14A—C15A125.8 (6)
C12—C13—H13119.6C13A—C14A—H14A117.1
C13—C14—C15125.7 (6)C15A—C14A—H14A117.1
C13—C14—H14117.2C15—C15A—C14A124.6 (6)
C15—C14—H14117.2C15—C15A—H15A117.7
C15A—C15—C14123.9 (6)C14A—C15A—H15A117.7
C15A—C15—H15118.0C1A—C16A—H16A109.5
C14—C15—H15118.0C1A—C16A—H16B109.5
C1—C16—H16D109.5H16A—C16A—H16B109.5
C1—C16—H16E109.5C1A—C16A—H16C109.5
H16D—C16—H16E109.5H16A—C16A—H16C109.5
C1—C16—H16F109.5H16B—C16A—H16C109.5
H16D—C16—H16F109.5C1A—C17A—H17A109.5
H16E—C16—H16F109.5C1A—C17A—H17B109.5
C1—C17—H17D109.5H17A—C17A—H17B109.5
C1—C17—H17E109.5C1A—C17A—H17C109.5
H17D—C17—H17E109.5H17A—C17A—H17C109.5
C1—C17—H17F109.5H17B—C17A—H17C109.5
H17D—C17—H17F109.5C5A—C18A—H18D109.5
H17E—C17—H17F109.5C5A—C18A—H18E109.5
C5—C18—H18A109.5H18D—C18A—H18E109.5
C5—C18—H18B109.5C5A—C18A—H18F109.5
H18A—C18—H18B109.5H18D—C18A—H18F109.5
C5—C18—H18C109.5H18E—C18A—H18F109.5
H18A—C18—H18C109.5C9A—C19A—H19D109.5
H18B—C18—H18C109.5C9A—C19A—H19E109.5
C9—C19—H19A109.5H19D—C19A—H19E109.5
C9—C19—H19B109.5C9A—C19A—H19F109.5
H19A—C19—H19B109.5H19D—C19A—H19F109.5
C9—C19—H19C109.5H19E—C19A—H19F109.5
H19A—C19—H19C109.5C13A—C20A—H20D109.5
H19B—C19—H19C109.5C13A—C20A—H20E109.5
C13—C20—H20A109.5H20D—C20A—H20E109.5
C13—C20—H20B109.5C13A—C20A—H20F109.5
C13—C20—H20C109.5H20D—C20A—H20F109.5
C2A—C1A—C6A111.8 (5)H20E—C20A—H20F109.5
C2A—C1A—C16A109.0 (4)
C17—C1—C2—C377.1 (6)C16A—C1A—C2A—C3A79.2 (6)
C6—C1—C2—C345.9 (6)C17A—C1A—C2A—C3A163.0 (4)
C16—C1—C2—C3165.9 (5)C1A—C2A—C3A—C4A61.8 (5)
C1—C2—C3—C464.0 (6)C2A—C3A—C4A—C5A49.9 (6)
C2—C3—C4—C546.0 (6)C3A—C4A—C5A—C6A19.5 (8)
C3—C4—C5—C613.2 (8)C3A—C4A—C5A—C18A160.8 (4)
C3—C4—C5—C18166.8 (4)C18A—C5A—C6A—C7A2.3 (9)
C18—C5—C6—C76.1 (9)C4A—C5A—C6A—C7A178.1 (5)
C4—C5—C6—C7173.9 (4)C18A—C5A—C6A—C1A177.3 (5)
C18—C5—C6—C1175.0 (5)C4A—C5A—C6A—C1A2.3 (9)
C4—C5—C6—C15.0 (9)C2A—C1A—C6A—C5A7.7 (7)
C17—C1—C6—C5112.3 (6)C16A—C1A—C6A—C5A112.3 (6)
C2—C1—C6—C511.2 (7)C17A—C1A—C6A—C5A128.8 (6)
C16—C1—C6—C5127.7 (6)C2A—C1A—C6A—C7A171.9 (4)
C17—C1—C6—C766.7 (6)C16A—C1A—C6A—C7A68.1 (6)
C2—C1—C6—C7169.9 (4)C17A—C1A—C6A—C7A50.8 (6)
C16—C1—C6—C753.4 (6)C5A—C6A—C7A—C8A47.3 (8)
C5—C6—C7—C853.2 (8)C1A—C6A—C7A—C8A133.1 (5)
C1—C6—C7—C8125.8 (6)C6A—C7A—C8A—C9A176.2 (5)
C6—C7—C8—C9176.2 (5)C7A—C8A—C9A—C10A175.1 (5)
C7—C8—C9—C10174.1 (5)C7A—C8A—C9A—C19A1.3 (8)
C7—C8—C9—C192.5 (8)C8A—C9A—C10A—C11A178.0 (5)
C8—C9—C10—C11175.7 (5)C19A—C9A—C10A—C11A1.8 (9)
C19—C9—C10—C110.7 (9)C9A—C10A—C11A—C12A179.0 (6)
C9—C10—C11—C12175.2 (6)C10A—C11A—C12A—C13A179.8 (6)
C10—C11—C12—C13173.2 (5)C11A—C12A—C13A—C14A177.5 (8)
C11—C12—C13—C14172.6 (5)C11A—C12A—C13A—C20A0.9 (13)
C11—C12—C13—C2013.5 (10)C12A—C13A—C14A—C15A178.3 (8)
C20—C13—C14—C159.4 (11)C20A—C13A—C14A—C15A3.4 (15)
C12—C13—C14—C15177.1 (6)C14—C15—C15A—C14A177.6 (7)
C13—C14—C15—C15A178.9 (7)C13A—C14A—C15A—C15177.3 (8)
C6A—C1A—C2A—C3A40.2 (6)
(I-P-1) 20-nor-β,β-carotene top
Crystal data top
C39H54Z = 2
Mr = 522.82F(000) = 576
Triclinic, P1Dx = 1.033 Mg m3
Hall symbol: -P1Mo Kα radiation, λ = 0.71073 Å
a = 8.5717 (13) ÅCell parameters from 2011 reflections
b = 14.089 (2) Åθ = 2.6–26.1°
c = 15.638 (2) ŵ = 0.06 mm1
α = 111.776 (2)°T = 100 K
β = 99.304 (3)°Needle, orange
γ = 99.084 (3)°0.90 × 0.10 × 0.10 mm
V = 1681.1 (4) Å3
Data collection top
Bruker SMART CCD area-detector
diffractometer
5808 independent reflections
Radiation source: fine-focus sealed tube3869 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.021
ϕ and ω scansθmax = 25.0°, θmin = 1.6°
Absorption correction: multi-scan
(SADABS; Bruker, 2001)
h = 1010
Tmin = 0.868, Tmax = 1.000k = 1615
8651 measured reflectionsl = 1418
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)] = 0.052Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.142H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.0693P)2 + 0.2096P]
where P = (Fo2 + 2Fc2)/3
5808 reflections(Δ/σ)max < 0.001
401 parametersΔρmax = 0.25 e Å3
4 restraintsΔρmin = 0.20 e Å3
Crystal data top
C39H54γ = 99.084 (3)°
Mr = 522.82V = 1681.1 (4) Å3
Triclinic, P1Z = 2
a = 8.5717 (13) ÅMo Kα radiation
b = 14.089 (2) ŵ = 0.06 mm1
c = 15.638 (2) ÅT = 100 K
α = 111.776 (2)°0.90 × 0.10 × 0.10 mm
β = 99.304 (3)°
Data collection top
Bruker SMART CCD area-detector
diffractometer
5808 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2001)
3869 reflections with I > 2σ(I)
Tmin = 0.868, Tmax = 1.000Rint = 0.021
8651 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0524 restraints
wR(F2) = 0.142H-atom parameters constrained
S = 1.02Δρmax = 0.25 e Å3
5808 reflectionsΔρmin = 0.20 e Å3
401 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)
C11.1180 (2)0.09320 (15)0.30506 (15)0.0350 (5)
C21.1933 (3)0.20139 (17)0.30088 (17)0.0480 (6)
H2A1.31060.20720.29880.058*
H2B1.18360.25640.24160.058*
C31.1144 (3)0.22144 (18)0.38408 (18)0.0533 (6)
H3A1.17160.29060.37950.064*
H3B1.12220.16650.44400.064*
C40.9374 (3)0.22025 (15)0.38439 (16)0.0420 (5)
H4A0.88010.21510.44680.050*
H4B0.93090.28760.33550.050*
C50.8515 (2)0.13035 (14)0.36546 (14)0.0338 (5)
C60.9310 (2)0.06916 (14)0.33553 (13)0.0302 (5)
C70.8462 (2)0.02787 (14)0.33076 (14)0.0303 (5)
H70.88370.03950.27570.036*
C80.7202 (2)0.10129 (14)0.39802 (14)0.0293 (4)
H80.68000.08790.45160.035*
C90.6401 (2)0.19929 (14)0.39605 (13)0.0278 (4)
C100.5076 (2)0.26266 (14)0.46655 (14)0.0302 (5)
H100.47570.24020.51560.036*
C110.4106 (2)0.36005 (14)0.47476 (14)0.0300 (4)
H110.43870.38290.42560.036*
C120.2820 (2)0.42124 (14)0.54796 (14)0.0292 (4)
H120.25760.39890.59790.035*
C130.1788 (2)0.51725 (14)0.55698 (14)0.0299 (5)
H130.20060.54410.51000.036*0.179 (4)
C140.0493 (2)0.56951 (14)0.63352 (14)0.0309 (5)
H140.03620.54070.67960.037*
C150.0684 (2)0.66287 (14)0.65168 (14)0.0307 (5)
H150.05900.69210.60580.037*
C161.1735 (3)0.09582 (17)0.20528 (15)0.0457 (6)
H16A1.29110.12570.18160.069*
H16B1.11660.13930.16230.069*
H16C1.14820.02410.20840.069*
C171.1802 (2)0.00773 (17)0.37518 (16)0.0438 (6)
H17A1.15340.00900.43800.066*
H17B1.29850.02090.35350.066*
H17C1.12860.06130.37880.066*
C180.6694 (2)0.11704 (16)0.38384 (16)0.0413 (5)
H18D0.62150.08310.45230.062*
H18E0.62390.07320.35350.062*
H18F0.64440.18620.35760.062*
C190.7102 (2)0.22572 (15)0.31606 (14)0.0324 (5)
H19D0.65390.29690.32720.049*
H19E0.82640.22220.31220.049*
H19F0.69630.17530.25640.049*
C200.2200 (3)0.55647 (17)0.47883 (16)0.0297 (7)0.821 (4)
H20A0.14060.62190.49340.044*0.821 (4)
H20B0.32940.56950.47520.044*0.821 (4)
H20C0.21650.50310.41780.044*0.821 (4)
C1A1.3792 (3)1.45421 (18)1.14460 (17)0.0475 (6)
C2A1.4463 (6)1.5817 (5)1.1883 (5)0.056 (2)0.542 (9)
H2C1.43781.61201.25500.067*0.542 (9)
H2D1.56271.59871.18800.067*0.542 (9)
C3A1.3520 (9)1.6324 (6)1.1325 (6)0.066 (2)0.542 (9)
H3C1.40301.70841.15630.079*0.542 (9)
H3D1.34951.59851.06420.079*0.542 (9)
C2B1.4504 (6)1.5457 (4)1.1220 (6)0.0394 (19)0.458 (9)
H2E1.57071.56341.14130.047*0.458 (9)
H2F1.41621.52771.05330.047*0.458 (9)
C3B1.3846 (8)1.6370 (6)1.1781 (6)0.0396 (18)0.458 (9)
H3E1.43541.70051.17030.047*0.458 (9)
H3F1.41661.65131.24630.047*0.458 (9)
C4A1.1916 (3)1.61701 (16)1.14698 (16)0.0506 (6)
H4C1.12131.63551.10180.061*
H4D1.19511.66751.21170.061*
C5A1.1108 (3)1.50842 (16)1.13633 (14)0.0378 (5)
C6A1.1935 (2)1.43461 (16)1.13337 (14)0.0365 (5)
C7A1.1127 (2)1.32683 (15)1.11778 (14)0.0334 (5)
H7A1.14991.30161.16400.040*
C8A0.9910 (2)1.26198 (15)1.04342 (14)0.0338 (5)
H8A0.95741.28740.99670.041*
C9A0.9049 (2)1.15692 (15)1.02665 (14)0.0313 (5)
C10A0.7734 (2)1.10635 (15)0.95189 (14)0.0346 (5)
H10A0.75181.13990.91010.042*
C11A0.6635 (2)1.00740 (14)0.92933 (14)0.0335 (5)
H11A0.67890.97520.97270.040*
C12A0.5399 (2)0.95691 (15)0.85092 (14)0.0343 (5)
H12A0.52620.98740.80610.041*
C13A0.4285 (2)0.86035 (15)0.83145 (15)0.0339 (5)
H13A0.43820.83170.87770.041*0.821 (4)
C14A0.3091 (2)0.80727 (14)0.75011 (14)0.0330 (5)
H14A0.30260.83520.70320.040*
C15A0.1929 (2)0.71239 (14)0.73035 (14)0.0319 (5)
H15A0.20360.68200.77540.038*
C16A1.4184 (10)1.4008 (8)1.0561 (5)0.067 (3)0.542 (9)
H16D1.53681.41101.06600.101*0.542 (9)
H16E1.37781.42921.01080.101*0.542 (9)
H16F1.36751.32541.03110.101*0.542 (9)
C16B1.4152 (12)1.3535 (6)1.0604 (6)0.048 (2)0.458 (9)
H16G1.53231.36531.06390.072*0.458 (9)
H16H1.35671.34640.99830.072*0.458 (9)
H16I1.37811.28891.06900.072*0.458 (9)
C17A1.4622 (3)1.4390 (2)1.23025 (16)0.0540 (6)
H17D1.42641.48041.28600.081*
H17E1.58041.46241.24160.081*
H17F1.43331.36441.21850.081*
C18A0.9309 (3)1.49491 (16)1.13137 (15)0.0438 (6)
H18A0.88551.42521.12860.066*
H18B0.87641.50151.07450.066*
H18C0.91411.54921.18780.066*
C19A0.9640 (2)1.11003 (15)1.09387 (14)0.0331 (5)
H19A0.89881.03811.07230.050*
H19B0.95331.15251.15740.050*
H19C1.07851.10881.09590.050*
C20A0.4736 (15)0.8123 (9)0.9053 (8)0.055 (4)0.179 (4)
H20D0.58280.79950.90600.083*0.179 (4)
H20E0.39460.74570.88750.083*0.179 (4)
H20F0.47160.86160.96850.083*0.179 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0225 (11)0.0353 (11)0.0397 (12)0.0025 (9)0.0004 (9)0.0137 (9)
C20.0297 (12)0.0441 (13)0.0601 (16)0.0077 (10)0.0022 (11)0.0201 (11)
C30.0505 (15)0.0451 (13)0.0646 (17)0.0037 (11)0.0129 (13)0.0292 (12)
C40.0460 (14)0.0326 (11)0.0427 (13)0.0037 (10)0.0044 (11)0.0149 (10)
C50.0316 (11)0.0268 (10)0.0329 (11)0.0016 (9)0.0013 (9)0.0059 (9)
C60.0236 (11)0.0280 (10)0.0310 (11)0.0001 (8)0.0025 (9)0.0072 (8)
C70.0225 (10)0.0317 (10)0.0341 (11)0.0050 (8)0.0051 (9)0.0117 (9)
C80.0216 (10)0.0298 (10)0.0341 (11)0.0040 (8)0.0043 (9)0.0121 (9)
C90.0190 (10)0.0291 (10)0.0326 (11)0.0058 (8)0.0063 (8)0.0095 (8)
C100.0238 (10)0.0300 (10)0.0341 (11)0.0037 (8)0.0029 (9)0.0126 (9)
C110.0224 (10)0.0302 (10)0.0345 (11)0.0061 (8)0.0053 (9)0.0108 (9)
C120.0214 (10)0.0288 (10)0.0344 (11)0.0060 (8)0.0054 (9)0.0101 (9)
C130.0215 (10)0.0283 (10)0.0354 (11)0.0070 (8)0.0076 (9)0.0074 (9)
C140.0220 (10)0.0294 (10)0.0374 (11)0.0067 (8)0.0070 (9)0.0092 (9)
C150.0220 (10)0.0310 (10)0.0345 (11)0.0062 (8)0.0062 (9)0.0086 (9)
C160.0257 (12)0.0529 (14)0.0465 (14)0.0029 (10)0.0041 (10)0.0172 (11)
C170.0246 (11)0.0514 (13)0.0509 (14)0.0054 (10)0.0066 (10)0.0182 (11)
C180.0338 (12)0.0339 (11)0.0481 (13)0.0080 (9)0.0010 (10)0.0114 (10)
C190.0230 (11)0.0321 (10)0.0371 (12)0.0021 (8)0.0031 (9)0.0122 (9)
C200.0224 (13)0.0276 (12)0.0332 (14)0.0045 (10)0.0023 (10)0.0084 (10)
C1A0.0252 (12)0.0622 (15)0.0518 (15)0.0108 (10)0.0028 (10)0.0331 (12)
C2A0.040 (3)0.070 (4)0.044 (4)0.022 (3)0.004 (3)0.027 (3)
C3A0.075 (5)0.060 (4)0.055 (4)0.023 (3)0.009 (4)0.033 (4)
C2B0.035 (3)0.043 (3)0.040 (4)0.002 (2)0.009 (3)0.019 (3)
C3B0.039 (4)0.035 (3)0.045 (5)0.003 (3)0.020 (4)0.015 (4)
C4A0.0608 (16)0.0407 (13)0.0364 (13)0.0090 (12)0.0038 (12)0.0152 (10)
C5A0.0378 (12)0.0376 (12)0.0275 (11)0.0064 (10)0.0025 (9)0.0119 (9)
C6A0.0285 (11)0.0420 (12)0.0329 (12)0.0060 (9)0.0008 (9)0.0178 (10)
C7A0.0217 (11)0.0421 (11)0.0343 (11)0.0021 (9)0.0038 (9)0.0166 (9)
C8A0.0252 (11)0.0387 (11)0.0347 (12)0.0021 (9)0.0025 (9)0.0160 (9)
C9A0.0203 (10)0.0354 (11)0.0336 (11)0.0053 (8)0.0034 (9)0.0107 (9)
C10A0.0257 (11)0.0368 (11)0.0363 (12)0.0040 (9)0.0003 (9)0.0136 (9)
C11A0.0249 (11)0.0330 (11)0.0380 (12)0.0064 (9)0.0035 (9)0.0113 (9)
C12A0.0229 (11)0.0339 (11)0.0409 (12)0.0050 (9)0.0051 (9)0.0114 (9)
C13A0.0227 (11)0.0323 (11)0.0385 (12)0.0047 (8)0.0069 (9)0.0065 (9)
C14A0.0207 (10)0.0320 (11)0.0415 (12)0.0063 (8)0.0082 (9)0.0094 (9)
C15A0.0209 (10)0.0306 (10)0.0378 (12)0.0067 (8)0.0069 (9)0.0069 (9)
C16A0.033 (3)0.121 (8)0.045 (3)0.017 (5)0.005 (2)0.048 (5)
C16B0.036 (4)0.071 (5)0.044 (4)0.005 (4)0.020 (3)0.030 (4)
C17A0.0301 (13)0.0829 (18)0.0436 (14)0.0102 (12)0.0042 (11)0.0229 (13)
C18A0.0417 (13)0.0398 (12)0.0429 (13)0.0055 (10)0.0002 (11)0.0150 (10)
C19A0.0239 (11)0.0345 (11)0.0338 (11)0.0051 (8)0.0031 (9)0.0084 (9)
C20A0.044 (8)0.038 (7)0.071 (10)0.014 (6)0.022 (7)0.002 (7)
Geometric parameters (Å, º) top
C1—C21.532 (3)C1A—C16B1.651 (8)
C1—C171.533 (3)C2A—C3A1.531 (11)
C1—C61.541 (3)C2A—H2C0.9900
C1—C161.541 (3)C2A—H2D0.9900
C2—C31.509 (3)C3A—C4A1.425 (7)
C2—H2A0.9900C3A—H3C0.9900
C2—H2B0.9900C3A—H3D0.9900
C3—C41.514 (3)C2B—C3B1.515 (11)
C3—H3A0.9900C2B—H2E0.9900
C3—H3B0.9900C2B—H2F0.9900
C4—C51.512 (3)C3B—C4A1.595 (7)
C4—H4A0.9900C3B—H3E0.9900
C4—H4B0.9900C3B—H3F0.9900
C5—C61.345 (3)C4A—C5A1.512 (3)
C5—C181.509 (3)C4A—H4C0.9900
C6—C71.477 (2)C4A—H4D0.9900
C7—C81.347 (2)C5A—C6A1.339 (3)
C7—H70.9500C5A—C18A1.509 (3)
C8—C91.455 (2)C6A—C7A1.478 (3)
C8—H80.9500C7A—C8A1.339 (3)
C9—C101.359 (2)C7A—H7A0.9500
C9—C191.496 (3)C8A—C9A1.452 (3)
C10—C111.437 (2)C8A—H8A0.9500
C10—H100.9500C9A—C10A1.359 (3)
C11—C121.352 (2)C9A—C19A1.499 (3)
C11—H110.9500C10A—C11A1.438 (3)
C12—C131.440 (2)C10A—H10A0.9500
C12—H120.9500C11A—C12A1.352 (3)
C13—C141.366 (3)C11A—H11A0.9500
C13—C201.532 (3)C12A—C13A1.430 (3)
C13—H130.9500C12A—H12A0.9500
C14—C151.429 (2)C13A—C14A1.362 (3)
C14—H140.9500C13A—C20A1.569 (9)
C15—C15A1.357 (3)C13A—H13A0.9500
C15—H150.9500C14A—C15A1.431 (3)
C16—H16A0.9800C14A—H14A0.9500
C16—H16B0.9800C15A—H15A0.9500
C16—H16C0.9800C16A—H16D0.9800
C17—H17A0.9800C16A—H16E0.9800
C17—H17B0.9800C16A—H16F0.9800
C17—H17C0.9800C16B—H16G0.9800
C18—H18D0.9800C16B—H16H0.9800
C18—H18E0.9800C16B—H16I0.9800
C18—H18F0.9800C17A—H17D0.9800
C19—H19D0.9800C17A—H17E0.9800
C19—H19E0.9800C17A—H17F0.9800
C19—H19F0.9800C18A—H18A0.9800
C20—H20A0.9800C18A—H18B0.9800
C20—H20B0.9800C18A—H18C0.9800
C20—H20C0.9800C19A—H19A0.9800
C1A—C16A1.432 (8)C19A—H19B0.9800
C1A—C17A1.516 (3)C19A—H19C0.9800
C1A—C2B1.521 (5)C20A—H20D0.9800
C1A—C6A1.541 (3)C20A—H20E0.9800
C1A—C2A1.631 (6)C20A—H20F0.9800
C2—C1—C17110.21 (18)C6A—C1A—C16B107.6 (4)
C2—C1—C6110.26 (17)C2A—C1A—C16B135.0 (4)
C17—C1—C6109.67 (16)C3A—C2A—C1A112.6 (5)
C2—C1—C16107.36 (17)C3A—C2A—H2C109.1
C17—C1—C16108.58 (18)C1A—C2A—H2C109.1
C6—C1—C16110.73 (16)C3A—C2A—H2D109.1
C3—C2—C1113.32 (18)C1A—C2A—H2D109.1
C3—C2—H2A108.9H2C—C2A—H2D107.8
C1—C2—H2A108.9C4A—C3A—C2A105.7 (6)
C3—C2—H2B108.9C4A—C3A—H3C110.6
C1—C2—H2B108.9C2A—C3A—H3C110.6
H2A—C2—H2B107.7C4A—C3A—H3D110.6
C2—C3—C4109.58 (19)C2A—C3A—H3D110.6
C2—C3—H3A109.8H3C—C3A—H3D108.7
C4—C3—H3A109.8C3B—C2B—C1A105.8 (6)
C2—C3—H3B109.8C3B—C2B—H2E110.6
C4—C3—H3B109.8C1A—C2B—H2E110.6
H3A—C3—H3B108.2C3B—C2B—H2F110.6
C5—C4—C3113.22 (18)C1A—C2B—H2F110.6
C5—C4—H4A108.9H2E—C2B—H2F108.7
C3—C4—H4A108.9C2B—C3B—C4A113.6 (6)
C5—C4—H4B108.9C2B—C3B—H3E108.8
C3—C4—H4B108.9C4A—C3B—H3E108.8
H4A—C4—H4B107.7C2B—C3B—H3F108.8
C6—C5—C18124.12 (18)C4A—C3B—H3F108.8
C6—C5—C4122.84 (18)H3E—C3B—H3F107.7
C18—C5—C4113.04 (17)C3A—C4A—C5A117.5 (4)
C5—C6—C7122.76 (18)C5A—C4A—C3B110.3 (3)
C5—C6—C1122.87 (17)C3A—C4A—H4C107.9
C7—C6—C1114.35 (16)C5A—C4A—H4C107.9
C8—C7—C6125.41 (18)C3B—C4A—H4C131.5
C8—C7—H7117.3C3A—C4A—H4D107.9
C6—C7—H7117.3C5A—C4A—H4D107.9
C7—C8—C9125.97 (19)C3B—C4A—H4D88.2
C7—C8—H8117.0H4C—C4A—H4D107.2
C9—C8—H8117.0C6A—C5A—C18A125.00 (18)
C10—C9—C8119.14 (18)C6A—C5A—C4A122.5 (2)
C10—C9—C19123.18 (17)C18A—C5A—C4A112.48 (19)
C8—C9—C19117.68 (16)C5A—C6A—C7A122.31 (19)
C9—C10—C11126.87 (18)C5A—C6A—C1A123.12 (19)
C9—C10—H10116.6C7A—C6A—C1A114.57 (19)
C11—C10—H10116.6C8A—C7A—C6A124.98 (19)
C12—C11—C10124.25 (19)C8A—C7A—H7A117.5
C12—C11—H11117.9C6A—C7A—H7A117.5
C10—C11—H11117.9C7A—C8A—C9A126.86 (19)
C11—C12—C13125.80 (19)C7A—C8A—H8A116.6
C11—C12—H12117.1C9A—C8A—H8A116.6
C13—C12—H12117.1C10A—C9A—C8A118.70 (18)
C14—C13—C12119.61 (18)C10A—C9A—C19A123.06 (18)
C14—C13—C20122.63 (17)C8A—C9A—C19A118.23 (17)
C12—C13—C20117.77 (17)C9A—C10A—C11A126.89 (19)
C14—C13—H13120.2C9A—C10A—H10A116.6
C12—C13—H13120.2C11A—C10A—H10A116.6
C13—C14—C15126.96 (19)C12A—C11A—C10A124.79 (19)
C13—C14—H14116.5C12A—C11A—H11A117.6
C15—C14—H14116.5C10A—C11A—H11A117.6
C15A—C15—C14124.12 (19)C11A—C12A—C13A123.9 (2)
C15A—C15—H15117.9C11A—C12A—H12A118.1
C14—C15—H15117.9C13A—C12A—H12A118.1
C1—C16—H16A109.5C14A—C13A—C12A123.5 (2)
C1—C16—H16B109.5C14A—C13A—C20A122.6 (5)
H16A—C16—H16B109.5C12A—C13A—C20A113.2 (5)
C1—C16—H16C109.5C14A—C13A—H13A118.2
H16A—C16—H16C109.5C12A—C13A—H13A118.2
H16B—C16—H16C109.5C13A—C14A—C15A124.6 (2)
C1—C17—H17A109.5C13A—C14A—H14A117.7
C1—C17—H17B109.5C15A—C14A—H14A117.7
H17A—C17—H17B109.5C15—C15A—C14A124.5 (2)
C1—C17—H17C109.5C15—C15A—H15A117.8
H17A—C17—H17C109.5C14A—C15A—H15A117.8
H17B—C17—H17C109.5C1A—C16A—H16D109.5
C5—C18—H18D109.5C1A—C16A—H16E109.5
C5—C18—H18E109.5C1A—C16A—H16F109.5
H18D—C18—H18E109.5C1A—C16B—H16G109.5
C5—C18—H18F109.5C1A—C16B—H16H109.5
H18D—C18—H18F109.5H16G—C16B—H16H109.5
H18E—C18—H18F109.5C1A—C16B—H16I109.5
C9—C19—H19D109.5H16G—C16B—H16I109.5
C9—C19—H19E109.5H16H—C16B—H16I109.5
H19D—C19—H19E109.5C1A—C17A—H17D109.5
C9—C19—H19F109.5C1A—C17A—H17E109.5
H19D—C19—H19F109.5H17D—C17A—H17E109.5
H19E—C19—H19F109.5C1A—C17A—H17F109.5
C13—C20—H20A109.5H17D—C17A—H17F109.5
C13—C20—H20B109.5H17E—C17A—H17F109.5
H20A—C20—H20B109.5C5A—C18A—H18A109.5
C13—C20—H20C109.5C5A—C18A—H18B109.5
H20A—C20—H20C109.5H18A—C18A—H18B109.5
H20B—C20—H20C109.5C5A—C18A—H18C109.5
C16A—C1A—C17A117.6 (4)H18A—C18A—H18C109.5
C16A—C1A—C2B78.2 (3)H18B—C18A—H18C109.5
C17A—C1A—C2B121.3 (3)C9A—C19A—H19A109.5
C16A—C1A—C6A111.1 (4)C9A—C19A—H19B109.5
C17A—C1A—C6A111.13 (18)H19A—C19A—H19B109.5
C2B—C1A—C6A113.6 (3)C9A—C19A—H19C109.5
C16A—C1A—C2A113.4 (4)H19A—C19A—H19C109.5
C17A—C1A—C2A96.6 (3)H19B—C19A—H19C109.5
C6A—C1A—C2A105.6 (3)C13A—C20A—H20D109.5
C17A—C1A—C16B98.9 (4)C13A—C20A—H20E109.5
C2B—C1A—C16B101.7 (3)C13A—C20A—H20F109.5
C17—C1—C2—C378.0 (2)C2A—C1A—C2B—C3B34.1 (6)
C6—C1—C2—C343.2 (3)C16B—C1A—C2B—C3B165.3 (7)
C16—C1—C2—C3163.96 (19)C1A—C2B—C3B—C4A63.6 (8)
C1—C2—C3—C462.5 (3)C2A—C3A—C4A—C5A46.3 (7)
C2—C3—C4—C544.3 (3)C2A—C3A—C4A—C3B33.5 (10)
C3—C4—C5—C610.7 (3)C2B—C3B—C4A—C3A65.8 (12)
C3—C4—C5—C18169.18 (19)C2B—C3B—C4A—C5A45.6 (8)
C18—C5—C6—C79.3 (3)C3A—C4A—C5A—C6A13.9 (5)
C4—C5—C6—C7170.60 (18)C3B—C4A—C5A—C6A13.4 (4)
C18—C5—C6—C1171.87 (19)C3A—C4A—C5A—C18A167.1 (4)
C4—C5—C6—C18.3 (3)C3B—C4A—C5A—C18A165.6 (4)
C2—C1—C6—C57.9 (3)C18A—C5A—C6A—C7A4.5 (3)
C17—C1—C6—C5113.6 (2)C4A—C5A—C6A—C7A176.63 (19)
C16—C1—C6—C5126.6 (2)C18A—C5A—C6A—C1A176.3 (2)
C2—C1—C6—C7173.13 (17)C4A—C5A—C6A—C1A2.6 (3)
C17—C1—C6—C765.3 (2)C16A—C1A—C6A—C5A107.9 (5)
C16—C1—C6—C754.5 (2)C17A—C1A—C6A—C5A119.0 (2)
C5—C6—C7—C843.6 (3)C2B—C1A—C6A—C5A21.9 (4)
C1—C6—C7—C8135.4 (2)C2A—C1A—C6A—C5A15.4 (4)
C6—C7—C8—C9177.23 (18)C16B—C1A—C6A—C5A133.7 (4)
C7—C8—C9—C10175.92 (19)C16A—C1A—C6A—C7A71.3 (5)
C7—C8—C9—C194.8 (3)C17A—C1A—C6A—C7A61.7 (3)
C8—C9—C10—C11177.98 (18)C2B—C1A—C6A—C7A157.3 (4)
C19—C9—C10—C112.8 (3)C2A—C1A—C6A—C7A165.3 (3)
C9—C10—C11—C12178.31 (19)C16B—C1A—C6A—C7A45.5 (4)
C10—C11—C12—C13177.71 (18)C5A—C6A—C7A—C8A56.1 (3)
C11—C12—C13—C14177.81 (18)C1A—C6A—C7A—C8A123.2 (2)
C11—C12—C13—C202.1 (3)C6A—C7A—C8A—C9A178.03 (19)
C12—C13—C14—C15177.37 (18)C7A—C8A—C9A—C10A173.5 (2)
C20—C13—C14—C152.5 (3)C7A—C8A—C9A—C19A5.5 (3)
C13—C14—C15—C15A178.60 (19)C8A—C9A—C10A—C11A173.30 (19)
C16A—C1A—C2A—C3A71.6 (8)C19A—C9A—C10A—C11A5.7 (3)
C17A—C1A—C2A—C3A164.5 (5)C9A—C10A—C11A—C12A175.8 (2)
C2B—C1A—C2A—C3A58.6 (6)C10A—C11A—C12A—C13A177.74 (19)
C6A—C1A—C2A—C3A50.3 (6)C11A—C12A—C13A—C14A176.67 (19)
C16B—C1A—C2A—C3A86.0 (8)C11A—C12A—C13A—C20A5.7 (6)
C1A—C2A—C3A—C4A66.5 (8)C12A—C13A—C14A—C15A177.86 (19)
C16A—C1A—C2B—C3B158.1 (7)C20A—C13A—C14A—C15A12.0 (6)
C17A—C1A—C2B—C3B86.6 (6)C14—C15—C15A—C14A178.49 (18)
C6A—C1A—C2B—C3B50.0 (7)C13A—C14A—C15A—C15176.08 (19)

Experimental details

(I-P21)(I-P-1)
Crystal data
Chemical formulaC39H54C39H54
Mr522.82522.82
Crystal system, space groupMonoclinic, P21Triclinic, P1
Temperature (K)100100
a, b, c (Å)9.442 (2), 7.6914 (16), 23.090 (5)8.5717 (13), 14.089 (2), 15.638 (2)
α, β, γ (°)90, 93.733 (3), 90111.776 (2), 99.304 (3), 99.084 (3)
V3)1673.3 (6)1681.1 (4)
Z22
Radiation typeMo KαMo Kα
µ (mm1)0.060.06
Crystal size (mm)0.40 × 0.22 × 0.050.90 × 0.10 × 0.10
Data collection
DiffractometerBruker SMART CCD area-detector
diffractometer
Bruker SMART CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2001)
Tmin, Tmax0.868, 1.000
No. of measured, independent and
observed [I > 2σ(I)] reflections
8554, 3196, 1530 8651, 5808, 3869
Rint0.0850.021
(sin θ/λ)max1)0.5950.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.058, 0.112, 0.85 0.052, 0.142, 1.02
No. of reflections31955808
No. of parameters373401
No. of restraints14
H-atom treatmentH-atom parameters constrainedH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.15, 0.150.25, 0.20

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Bruker, 2001).

Torsion angles (°) about the cyclohexene ring bonds of (I)-P21 and (I)-P1; the C5—C6—C7—C8 torsion angle gives a measure of the angle of twist of the end rings from the plane of the polyene chain top
(I)-P21(I)-P21A(I)-P1(I)-P1 A(I)-P1B
ϕ1–245.9 (6)-40.2 (6)43.2 (3)-50.3 (6)50.0 (7)
ϕ2–3-64.0 (6)61.8 (5)-62.5 (3)66.5 (8)-63.6 (8)
ϕ3–446.0 (6)-49.9 (6)44.3 (3)-46.3 (7)45.6 (8)
ϕ4–5-13.2 (8)19.5 (8)-10.7 (3)13.9 (5)-13.4 (4)
ϕ5–6-5.0 (9)2.3 (9)-8.3 (3)2.6 (3)
ϕ6–1-11.2 (7)7.7 (7)-7.9 (3)15.4 (4)
C5-C6-C7-C8-53.2 (8)47.3 (8)-41.4 (2)56.1 (3)
 

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
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds