Buy article online - an online subscription or single-article purchase is required to access this article.
Download citation
Download citation
link to html
In the title inclusion compound, 2C34H34O4·C13H19NO2, the N-allyl moiety is located closer to the cyclo­hexenone ring than the N-propyl group in the guest amide. In the crystal structure, two keto O atoms of the guest mol­ecule act as acceptors of O—H...O hydrogen bonds with the two host mol­ecules.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803008080/su6022sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803008080/su6022Isup2.hkl
Contains datablock I

CCDC reference: 214612

Key indicators

  • Single-crystal X-ray study
  • T = 248 K
  • Mean [sigma](C-C) = 0.009 Å
  • R factor = 0.062
  • wR factor = 0.172
  • Data-to-parameter ratio = 7.0

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


Yellow Alert Alert Level C:
REFNR_01 Alert C Ratio of reflections to parameters is < 8 for a non-centrosymmetric structure, where ZMAX < 18 sine(theta)/lambda 0.5878 Proportion of unique data used 1.0000 Ratio reflections to parameters 6.9700 THETM_01 Alert C The value of sine(theta_max)/wavelength is less than 0.590 Calculated sin(theta_max)/wavelength = 0.5878 PLAT_360 Alert C Short C(sp3)-C(sp3) Bond C(22) - C(23) = 1.43 Ang. General Notes
REFLT_03 From the CIF: _diffrn_reflns_theta_max 65.00 From the CIF: _reflns_number_total 5806 Count of symmetry unique reflns 5866 Completeness (_total/calc) 98.98% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 0 Fraction of Friedel pairs measured 0.000 Are heavy atom types Z>Si present no Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF.
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
3 Alert Level C = Please check

Comment top

Organic solid-state photoreactions of guest molecules in inclusion compounds with chiral hosts are efficient methods to achieve regioselective and enantioselective syntheses (Tanaka et al., 1992; Toda et al., 1993). The enantioselective intramolecular photocyclization reaction of N-allyl-NR-3-oxo-1-cyclohexenecarboxamides (R = Me, Et, nPr etc) in inclusion crystals was reported by Toda et al. (1995). The products obtained were tricyclic compounds as the result of a [2 + 2]-photoreaction in the guest molecule, except for that of R = nPr, which gave the spiramic β-lactam (A in Scheme 2), not the expected tricyclic compound (B). The crystal structure of the title compound, (I), has been determined to investigate the conformation of the guest amide (R = nPr).

The n-propyl atoms C23 and C24 of the guest molecule show large elongated displacement ellipsoids, suggesting some positional disorder (Fig. 1). On the other hand, the N-allyl group C19/C20/C21 has normal displacement parameters and normal geometry (Table 1). The center-to-center distance between the C16C17 and C20C21 double bonds is 4.23 (1) Å, and they are inclined to one another by an angle of 95.0 (7)°. This arrangement is not suitable for the [2 + 2]-photocyclization, and will give product (C) not (A), as shown in Scheme 2. Therefore, the structure determined in the present study is not consistent with the photoreactivity reported by Toda et al. (1995). One of the possibilities, which could cause this inconsistency is a relatively rare polymorphism of these inclusion compounds (Ohba et al., 2000). In (I), the host molecule itself shows polymorphism; orthorhombic (Toda et al., 1997; Nishikawa et al., 1998) and triclinic (Hamazaki et al., 1999).

There are two independent host molecules in (I), which have a similar conformation (Fig. 2). There is an intramolecular O—H···O hydrogen bond in both host molecules (Table 2). The guest molecule is also connected to the two host molecules by O—H···O hydrogen bonds (Table 2 and Fig. 3).

For a six-membered ring host, as in (I), and a corresponding five-membered ring host, which differ only in the size of cycloalkane ring, it has been found that the crystal structures of their clathrate compounds are usually different (Ohba et al., 2000). However, the crystal structure of an inclusion compound (II) of the same guest amide (R = nPr), with the corresponding five-membered ring host, was not determined in the present study. There were too many parameters, the number of independent host and guest molecules being four and two, respectively. The crystals of (II) grown from a diethyl ether solution are colourless prisms; 2C33H32O4·C13H19NO2, triclinic, space group P1, a = 34.738 (4), b = 9.5934 (12), c = 10.0715 (19) Å, α = 90.278 (12), β = 93.993 (11), γ = 90.021 (10)°, V = 3348.2 (8) Å3, Z = 2 at 248 K. The crystal structure of the inclusion compound (III) of a guest amide (R = benzyl) with a five-membered ring host (host/guest = 2/1) has been reported by Akutsu et al. (1996). In (III), the N-allyl moiety is located close to the cyclohexenone ring and shows the suitable arrangement for [2 + 2]-photocyclization, as expected by the reactivity data (Toda et al., 1995).

Experimental top

The title inclusion compound, (I), was prepared by Toda et al. (1995). Suitable crystals of (I) were grown from a toluene solution.

Refinement top

The reflections with θ > 60° could not be measured due to the blind region of the four-circle diffractometer combined with a cooling aparatus. The hydroxyl H atoms were located from difference syntheses and allowed to ride on the O atoms with Uiso(H) = Ueq(O). The other H-atom positional parameters were calculated geometrically and fixed with Uiso(H) = 1.2Ueq(parent atom). The absolute structure was assigned based on the known absolute configuration of the host molecule derived from (+)-tartaric acid (Toda & Tanaka, 1988). The Flack (1983) parameter (1983) was −1.0 (5) before the Friedel pairs were averaged. The n-propyl atoms C23 and C24 of the guest molecule show large anisotropic displacement parameters, suggesting positional disorder.

Computing details top

Data collection: WinAFC Diffractometer Control Software (Rigaku, 1999); cell refinement: WinAFC Diffractometer Control Software; data reduction: TEXSAN (Molecular Structure Corporation, 2001); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: TEXSAN.

Figures top
[Figure 1] Fig. 1. The structure of the guest molecule, with displacement ellipsoids plotted at the 50% probability level.
[Figure 2] Fig. 2. The structures of the two independent host molecules, with displacement ellipsoids plotted at the 50% probability level.
[Figure 3] Fig. 3. The projection of the crystal structure of (I) viewed along c, with thin lines indicating hydrogen bonding.
(I) top
Crystal data top
2C34H34O4·C13H19NO2F(000) = 1320
Mr = 1234.58Dx = 1.209 Mg m3
Monoclinic, P21Cu Kα radiation, λ = 1.5418 Å
a = 10.4041 (16) ÅCell parameters from 25 reflections
b = 34.308 (4) Åθ = 25.3–27.4°
c = 9.5158 (12) ŵ = 0.62 mm1
β = 93.338 (11)°T = 248 K
V = 3390.8 (8) Å3Needle, colourless
Z = 20.8 × 0.2 × 0.05 mm
Data collection top
Rigaku AFC-7R
diffractometer
Rint = 0.081
ω–2θ scansθmax = 65°
Absorption correction: integration
(Coppens et al., 1965)
h = 512
Tmin = 0.831, Tmax = 0.969k = 039
6683 measured reflectionsl = 1111
5806 independent reflections3 standard reflections every 150 reflections
4617 reflections with I > 2σ(I) intensity decay: 4.7%
Refinement top
Refinement on F2H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.062 w = 1/[σ2(Fo2) + (0.125P)2 + 0.2381P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.172(Δ/σ)max = 0.002
S = 1.02Δρmax = 0.27 e Å3
5806 reflectionsΔρmin = 0.32 e Å3
833 parameters
Crystal data top
2C34H34O4·C13H19NO2V = 3390.8 (8) Å3
Mr = 1234.58Z = 2
Monoclinic, P21Cu Kα radiation
a = 10.4041 (16) ŵ = 0.62 mm1
b = 34.308 (4) ÅT = 248 K
c = 9.5158 (12) Å0.8 × 0.2 × 0.05 mm
β = 93.338 (11)°
Data collection top
Rigaku AFC-7R
diffractometer
4617 reflections with I > 2σ(I)
Absorption correction: integration
(Coppens et al., 1965)
Rint = 0.081
Tmin = 0.831, Tmax = 0.9693 standard reflections every 150 reflections
6683 measured reflections intensity decay: 4.7%
5806 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.062833 parameters
wR(F2) = 0.172H-atom parameters constrained
S = 1.02Δρmax = 0.27 e Å3
5806 reflectionsΔρmin = 0.32 e Å3
Special details top

Refinement. Refinement using reflections with F2 > 0.0 σ(F2). The weighted R-factor (wR), goodness of fit (S) and R-factor (gt) are based on F, with F set to zero for negative F. The threshold expression of F2 > 2.0 σ(F2) is used only for calculating R-factor (gt).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.5512 (5)0.5769 (1)0.2632 (5)0.079 (1)
O20.5421 (6)0.4653 (1)0.6805 (6)0.097 (2)
O30.4180 (4)0.4295 (1)0.3037 (5)0.077 (1)
O40.5917 (3)0.4049 (1)0.5038 (4)0.0547 (8)
O50.2304 (3)0.34563 (9)0.4055 (3)0.0490 (7)
O60.3552 (3)0.33290 (9)0.6051 (3)0.0493 (7)
O70.6592 (3)0.63066 (9)0.0787 (3)0.0470 (7)
O80.8161 (3)0.6045 (1)0.1142 (4)0.0601 (9)
O90.9193 (3)0.69441 (9)0.2119 (3)0.0476 (7)
O101.0340 (3)0.68063 (9)0.0209 (3)0.0474 (7)
N110.5029 (6)0.5199 (2)0.7985 (7)0.088 (2)
C120.6100 (7)0.5596 (2)0.3586 (7)0.072 (1)
C130.7563 (8)0.5571 (3)0.367 (1)0.105 (3)
C140.8099 (9)0.5232 (3)0.445 (1)0.120 (3)
C150.7560 (8)0.5183 (3)0.587 (1)0.105 (3)
C160.6131 (6)0.5231 (2)0.5816 (7)0.072 (2)
C170.5464 (7)0.5411 (2)0.4752 (8)0.079 (2)
C180.5483 (7)0.5006 (2)0.6913 (7)0.072 (2)
C190.5202 (8)0.5633 (2)0.8170 (10)0.093 (2)
C200.4029 (9)0.5861 (3)0.779 (1)0.114 (3)
C210.3677 (8)0.6162 (3)0.856 (1)0.106 (3)
C220.440 (1)0.4984 (4)0.910 (1)0.137 (4)
C230.514 (3)0.4970 (8)1.041 (1)0.27 (2)
C240.652 (3)0.4867 (5)1.035 (3)0.23 (1)
C250.3031 (5)0.4069 (1)0.3243 (5)0.050 (1)
C260.3452 (4)0.3680 (1)0.3937 (5)0.0469 (9)
C270.4015 (4)0.3685 (1)0.5476 (5)0.0435 (9)
C280.5515 (4)0.3692 (1)0.5696 (5)0.0470 (9)
C290.2521 (4)0.3180 (1)0.5142 (5)0.0435 (9)
C300.1303 (5)0.3156 (2)0.5968 (5)0.054 (1)
C310.0197 (5)0.2975 (2)0.5062 (6)0.063 (1)
C320.0561 (5)0.2581 (2)0.4482 (6)0.064 (1)
C330.1756 (5)0.2614 (2)0.3649 (6)0.059 (1)
C340.2888 (5)0.2788 (1)0.4523 (5)0.051 (1)
C350.2145 (6)0.4290 (2)0.4153 (5)0.062 (1)
C360.2621 (9)0.4600 (2)0.5007 (8)0.093 (2)
C370.189 (1)0.4792 (3)0.591 (1)0.121 (4)
C380.067 (1)0.4680 (3)0.5986 (8)0.119 (4)
C390.008 (1)0.4382 (3)0.517 (1)0.120 (4)
C400.0881 (8)0.4186 (2)0.4189 (7)0.079 (2)
C410.2437 (4)0.4017 (1)0.1735 (5)0.050 (1)
C420.2048 (7)0.4346 (2)0.1001 (6)0.070 (1)
C430.1602 (7)0.4328 (2)0.0371 (7)0.079 (2)
C440.1473 (6)0.3977 (2)0.1063 (6)0.068 (1)
C450.1822 (6)0.3646 (2)0.0349 (6)0.066 (1)
C460.2301 (5)0.3661 (2)0.1041 (5)0.056 (1)
C470.5995 (4)0.3709 (1)0.7227 (5)0.0470 (9)
C480.7334 (5)0.3729 (2)0.7537 (6)0.062 (1)
C490.7839 (6)0.3773 (2)0.8893 (7)0.071 (2)
C500.7043 (6)0.3789 (2)1.0017 (6)0.067 (1)
C510.5736 (6)0.3764 (2)0.9726 (6)0.068 (1)
C520.5208 (5)0.3726 (2)0.8382 (5)0.053 (1)
C530.6103 (4)0.3352 (2)0.4950 (5)0.049 (1)
C540.6633 (5)0.3398 (2)0.3646 (5)0.061 (1)
C550.7108 (6)0.3078 (2)0.2968 (7)0.076 (2)
C560.7070 (6)0.2712 (2)0.3516 (7)0.072 (2)
C570.6578 (5)0.2665 (2)0.4839 (7)0.066 (1)
C580.6099 (5)0.2982 (2)0.5548 (5)0.055 (1)
C590.7110 (4)0.6652 (1)0.1501 (4)0.0388 (8)
C600.8592 (4)0.6615 (1)0.1441 (4)0.0424 (9)
C610.9143 (4)0.6607 (1)0.0037 (5)0.0433 (9)
C620.9387 (4)0.6204 (1)0.0714 (5)0.0486 (10)
C631.0209 (4)0.7087 (1)0.1289 (5)0.0451 (9)
C640.9831 (5)0.7485 (1)0.0661 (5)0.0481 (10)
C651.0917 (5)0.7665 (2)0.0114 (6)0.060 (1)
C661.2155 (6)0.7685 (2)0.0791 (6)0.066 (1)
C671.2543 (5)0.7285 (2)0.1359 (6)0.057 (1)
C681.1451 (5)0.7107 (1)0.2174 (5)0.0490 (10)
C690.6586 (4)0.7013 (1)0.0720 (5)0.0417 (9)
C700.6102 (5)0.6995 (2)0.0658 (5)0.052 (1)
C710.5629 (6)0.7326 (2)0.1345 (6)0.064 (1)
C720.5647 (5)0.7683 (2)0.0644 (7)0.066 (1)
C730.6120 (5)0.7702 (2)0.0719 (6)0.060 (1)
C740.6594 (5)0.7371 (1)0.1406 (5)0.0480 (10)
C750.6664 (4)0.6648 (1)0.3004 (5)0.0440 (9)
C760.5323 (5)0.6656 (2)0.3137 (5)0.053 (1)
C770.4826 (5)0.6629 (2)0.4461 (6)0.067 (1)
C780.5628 (6)0.6591 (2)0.5633 (6)0.069 (1)
C790.6944 (6)0.6589 (2)0.5531 (6)0.070 (1)
C800.7459 (5)0.6615 (2)0.4207 (5)0.054 (1)
C811.0072 (4)0.6236 (1)0.2096 (5)0.0482 (10)
C821.0343 (6)0.5888 (2)0.2766 (6)0.061 (1)
C831.0865 (7)0.5893 (2)0.4095 (7)0.072 (2)
C841.1097 (6)0.6238 (2)0.4760 (6)0.066 (1)
C851.0846 (6)0.6585 (2)0.4096 (6)0.064 (1)
C861.0320 (5)0.6582 (2)0.2771 (5)0.057 (1)
C871.0143 (6)0.5930 (2)0.0308 (5)0.060 (1)
C880.9625 (8)0.5576 (2)0.0687 (10)0.093 (2)
C891.034 (1)0.5325 (3)0.161 (1)0.121 (4)
C901.154 (1)0.5424 (3)0.2123 (9)0.116 (4)
C911.2065 (9)0.5772 (3)0.1757 (9)0.100 (3)
C921.1376 (6)0.6022 (2)0.0849 (6)0.070 (1)
H30.47170.42510.36830.0772*
H40.59080.42290.56070.0547*
H70.63320.61540.13700.0470*
H80.76490.60910.05400.0601*
H13A0.78960.58010.41110.1262*
H13B0.78400.55580.27330.1262*
H14A0.90040.52630.45770.1435*
H14B0.79080.50030.39140.1435*
H15A0.79380.53740.64940.1256*
H15B0.77730.49310.62200.1256*
H170.45520.54200.47550.0942*
H19A0.58630.57170.75920.1116*
H19B0.54520.56840.91290.1116*
H200.35110.57900.69750.1370*
H21A0.29160.63040.82970.1269*
H21B0.41860.62350.93830.1269*
H22A0.42310.47260.87820.1641*
H22B0.36040.51100.92610.1641*
H23A0.47800.47771.09850.3350*
H23B0.51100.52151.08470.3350*
H24A0.69530.48891.12580.2871*
H24B0.69290.50420.97230.2871*
H24C0.66180.46081.00130.2871*
H260.40220.35470.33580.0562*
H270.36660.39000.59570.0522*
H30A0.10650.34110.62430.0644*
H30B0.14730.30000.67830.0644*
H31A0.00260.31450.43000.0750*
H31B0.05230.29430.56220.0750*
H32A0.01310.24860.38830.0767*
H32B0.07260.24040.52400.0767*
H33A0.15670.27770.28550.0712*
H33B0.19870.23620.33410.0712*
H34A0.35900.28240.39410.0616*
H34B0.31350.26140.52680.0616*
H360.34940.46760.49500.1115*
H370.22330.50010.64650.1447*
H380.01600.48100.66410.1434*
H390.07980.43130.52480.1435*
H400.05310.39880.35810.0950*
H420.20920.45920.14620.0839*
H430.13770.45610.08610.0948*
H440.11480.39650.20160.0813*
H450.17360.34010.08100.0793*
H460.25380.34280.15240.0678*
H480.79000.37110.67900.0741*
H490.87460.37930.90670.0848*
H500.73940.38171.09560.0803*
H510.51800.37741.04840.0819*
H520.42990.37110.82240.0637*
H540.66660.36490.32270.0725*
H550.74760.31150.20860.0913*
H560.73700.24940.30110.0868*
H570.65700.24130.52580.0795*
H580.57680.29460.64480.0657*
H600.88650.63860.19360.0509*
H610.86000.67560.06670.0519*
H64A0.96160.76550.14000.0576*
H64B0.91040.74520.00200.0576*
H65A1.06760.79220.03950.0722*
H65B1.10560.75120.09240.0722*
H66A1.20410.78560.15580.0792*
H66B1.28190.77820.02420.0792*
H67A1.32920.73090.19730.0680*
H67B1.27210.71180.05970.0680*
H68A1.13260.72620.29800.0588*
H68B1.16910.68510.24620.0588*
H700.60940.67530.11430.0622*
H710.52900.73090.22930.0769*
H720.53340.79110.11140.0789*
H730.61250.79440.12040.0720*
H740.69280.73890.23540.0577*
H760.47560.66800.23230.0638*
H770.39210.66380.45460.0797*
H780.52790.65650.65290.0828*
H790.74990.65700.63560.0841*
H800.83660.66090.41390.0651*
H821.01730.56460.23240.0736*
H831.10610.56530.45390.0868*
H841.14280.62390.56700.0795*
H851.10300.68250.45350.0765*
H861.01290.68220.23320.0679*
H880.87880.55030.03270.1121*
H890.99860.50820.18670.1455*
H901.20110.52520.27430.1396*
H911.29020.58430.21230.1202*
H921.17550.62610.05890.0843*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.099 (3)0.055 (2)0.085 (3)0.005 (2)0.011 (2)0.015 (2)
O20.147 (5)0.055 (3)0.089 (3)0.014 (3)0.011 (3)0.004 (2)
O30.082 (3)0.071 (2)0.075 (2)0.033 (2)0.018 (2)0.035 (2)
O40.060 (2)0.049 (2)0.055 (2)0.015 (2)0.007 (2)0.009 (1)
O50.046 (2)0.044 (2)0.056 (2)0.007 (1)0.002 (1)0.010 (1)
O60.052 (2)0.044 (2)0.051 (2)0.010 (1)0.001 (1)0.010 (1)
O70.053 (2)0.040 (2)0.048 (2)0.006 (1)0.006 (1)0.000 (1)
O80.055 (2)0.056 (2)0.070 (2)0.011 (2)0.013 (2)0.022 (2)
O90.050 (2)0.049 (2)0.044 (2)0.012 (1)0.009 (1)0.004 (1)
O100.045 (2)0.045 (2)0.053 (2)0.004 (1)0.007 (1)0.005 (1)
N110.106 (4)0.078 (4)0.083 (4)0.026 (3)0.020 (3)0.008 (3)
C120.088 (4)0.050 (3)0.079 (4)0.006 (3)0.010 (3)0.011 (3)
C130.094 (5)0.090 (5)0.137 (7)0.016 (4)0.048 (5)0.029 (5)
C140.100 (6)0.119 (7)0.144 (8)0.021 (5)0.026 (5)0.050 (6)
C150.082 (5)0.112 (6)0.121 (6)0.005 (4)0.003 (4)0.033 (5)
C160.080 (4)0.065 (3)0.072 (4)0.009 (3)0.006 (3)0.008 (3)
C170.083 (4)0.068 (4)0.086 (4)0.003 (3)0.011 (3)0.010 (3)
C180.089 (4)0.044 (3)0.081 (4)0.014 (3)0.001 (3)0.001 (3)
C190.087 (4)0.074 (4)0.118 (6)0.010 (3)0.004 (4)0.025 (4)
C200.085 (5)0.121 (7)0.135 (8)0.010 (5)0.009 (5)0.017 (6)
C210.075 (4)0.102 (6)0.142 (8)0.009 (4)0.026 (4)0.003 (6)
C220.20 (1)0.127 (8)0.091 (6)0.074 (8)0.050 (7)0.017 (5)
C230.47 (4)0.26 (3)0.081 (7)0.23 (3)0.03 (1)0.04 (1)
C240.33 (3)0.103 (9)0.24 (2)0.05 (1)0.13 (2)0.03 (1)
C250.060 (3)0.036 (2)0.053 (3)0.009 (2)0.005 (2)0.008 (2)
C260.050 (2)0.038 (2)0.053 (2)0.006 (2)0.002 (2)0.002 (2)
C270.047 (2)0.036 (2)0.048 (2)0.004 (2)0.006 (2)0.003 (2)
C280.046 (2)0.044 (2)0.051 (2)0.007 (2)0.007 (2)0.003 (2)
C290.044 (2)0.045 (2)0.042 (2)0.002 (2)0.004 (2)0.005 (2)
C300.053 (3)0.058 (3)0.051 (3)0.007 (2)0.013 (2)0.001 (2)
C310.050 (3)0.062 (3)0.076 (3)0.011 (2)0.008 (2)0.003 (3)
C320.061 (3)0.054 (3)0.076 (4)0.015 (2)0.002 (3)0.001 (3)
C330.070 (3)0.050 (3)0.058 (3)0.002 (2)0.002 (2)0.003 (2)
C340.061 (3)0.041 (2)0.052 (3)0.003 (2)0.004 (2)0.002 (2)
C350.089 (4)0.048 (3)0.049 (3)0.016 (3)0.000 (2)0.005 (2)
C360.141 (7)0.061 (4)0.073 (4)0.034 (4)0.026 (4)0.016 (3)
C370.156 (9)0.093 (6)0.109 (7)0.061 (7)0.036 (7)0.033 (5)
C380.19 (1)0.110 (7)0.059 (4)0.085 (7)0.005 (5)0.014 (4)
C390.144 (8)0.114 (7)0.107 (6)0.066 (6)0.048 (6)0.035 (6)
C400.098 (5)0.065 (4)0.077 (4)0.026 (3)0.021 (3)0.005 (3)
C410.048 (2)0.048 (2)0.053 (2)0.002 (2)0.002 (2)0.004 (2)
C420.095 (4)0.049 (3)0.065 (3)0.004 (3)0.008 (3)0.008 (3)
C430.106 (5)0.074 (4)0.056 (3)0.013 (3)0.007 (3)0.014 (3)
C440.070 (3)0.081 (4)0.051 (3)0.007 (3)0.007 (2)0.004 (3)
C450.070 (3)0.066 (3)0.062 (3)0.006 (3)0.002 (2)0.010 (3)
C460.065 (3)0.051 (3)0.054 (3)0.004 (2)0.001 (2)0.002 (2)
C470.052 (2)0.043 (2)0.045 (2)0.008 (2)0.002 (2)0.002 (2)
C480.060 (3)0.073 (3)0.052 (3)0.005 (3)0.000 (2)0.001 (2)
C490.058 (3)0.087 (4)0.066 (3)0.009 (3)0.006 (3)0.004 (3)
C500.084 (4)0.071 (4)0.044 (3)0.015 (3)0.007 (2)0.001 (2)
C510.084 (4)0.070 (4)0.051 (3)0.015 (3)0.008 (3)0.002 (2)
C520.063 (3)0.057 (3)0.040 (2)0.012 (2)0.010 (2)0.003 (2)
C530.045 (2)0.059 (3)0.042 (2)0.003 (2)0.003 (2)0.005 (2)
C540.062 (3)0.071 (3)0.048 (3)0.009 (2)0.007 (2)0.001 (2)
C550.068 (3)0.102 (5)0.059 (3)0.007 (3)0.006 (3)0.009 (3)
C560.060 (3)0.081 (4)0.075 (4)0.014 (3)0.005 (3)0.029 (3)
C570.055 (3)0.057 (3)0.084 (4)0.010 (2)0.014 (3)0.010 (3)
C580.050 (2)0.061 (3)0.053 (3)0.004 (2)0.002 (2)0.003 (2)
C590.045 (2)0.032 (2)0.039 (2)0.002 (2)0.001 (2)0.002 (2)
C600.048 (2)0.035 (2)0.043 (2)0.000 (2)0.002 (2)0.001 (2)
C610.043 (2)0.041 (2)0.047 (2)0.001 (2)0.002 (2)0.001 (2)
C620.050 (2)0.043 (2)0.053 (3)0.000 (2)0.006 (2)0.002 (2)
C630.047 (2)0.040 (2)0.050 (2)0.006 (2)0.010 (2)0.003 (2)
C640.052 (2)0.044 (2)0.048 (2)0.001 (2)0.006 (2)0.001 (2)
C650.063 (3)0.049 (3)0.070 (3)0.007 (2)0.014 (2)0.013 (2)
C660.067 (3)0.057 (3)0.074 (3)0.016 (3)0.011 (3)0.011 (3)
C670.045 (2)0.064 (3)0.060 (3)0.004 (2)0.004 (2)0.002 (2)
C680.052 (2)0.049 (2)0.046 (2)0.002 (2)0.003 (2)0.004 (2)
C690.040 (2)0.038 (2)0.048 (2)0.000 (2)0.009 (2)0.004 (2)
C700.055 (3)0.052 (3)0.050 (2)0.004 (2)0.006 (2)0.004 (2)
C710.071 (3)0.068 (3)0.052 (3)0.004 (3)0.001 (2)0.017 (3)
C720.067 (3)0.053 (3)0.079 (4)0.009 (2)0.014 (3)0.022 (3)
C730.058 (3)0.043 (3)0.081 (4)0.004 (2)0.016 (2)0.003 (2)
C740.053 (2)0.036 (2)0.056 (3)0.000 (2)0.009 (2)0.002 (2)
C750.044 (2)0.035 (2)0.053 (2)0.006 (2)0.005 (2)0.001 (2)
C760.055 (3)0.053 (3)0.052 (2)0.000 (2)0.010 (2)0.000 (2)
C770.065 (3)0.062 (3)0.076 (4)0.011 (3)0.029 (3)0.007 (3)
C780.083 (4)0.068 (3)0.058 (3)0.018 (3)0.020 (3)0.003 (3)
C790.087 (4)0.076 (4)0.046 (3)0.016 (3)0.000 (2)0.004 (3)
C800.062 (3)0.054 (3)0.048 (2)0.011 (2)0.006 (2)0.004 (2)
C810.047 (2)0.048 (2)0.050 (2)0.003 (2)0.002 (2)0.005 (2)
C820.074 (3)0.049 (3)0.061 (3)0.002 (2)0.009 (2)0.012 (2)
C830.087 (4)0.063 (3)0.069 (4)0.010 (3)0.016 (3)0.014 (3)
C840.072 (3)0.074 (4)0.054 (3)0.012 (3)0.012 (2)0.005 (3)
C850.078 (3)0.058 (3)0.056 (3)0.007 (3)0.012 (2)0.007 (2)
C860.074 (3)0.048 (3)0.049 (3)0.010 (2)0.012 (2)0.002 (2)
C870.080 (4)0.047 (3)0.055 (3)0.016 (2)0.020 (3)0.003 (2)
C880.111 (5)0.049 (3)0.124 (6)0.017 (3)0.045 (5)0.023 (4)
C890.161 (9)0.072 (5)0.139 (8)0.048 (6)0.078 (7)0.051 (5)
C900.166 (10)0.106 (7)0.080 (5)0.078 (7)0.027 (6)0.021 (5)
C910.118 (6)0.096 (6)0.084 (5)0.055 (5)0.014 (4)0.016 (4)
C920.081 (4)0.072 (4)0.057 (3)0.027 (3)0.001 (3)0.002 (3)
Geometric parameters (Å, º) top
O1—C121.218 (8)C45—C461.387 (8)
O2—C181.216 (7)C45—H450.950
O3—C251.447 (7)C46—H460.950
O3—H30.820C47—C481.410 (7)
O4—C281.449 (6)C47—C521.409 (7)
O4—H40.820C48—C491.373 (8)
O5—C261.431 (5)C48—H480.950
O5—C291.413 (5)C49—C501.392 (9)
O6—C271.434 (5)C49—H490.950
O6—C291.433 (5)C50—C511.375 (9)
O7—C591.454 (5)C50—H500.950
O7—H70.820C51—C521.369 (7)
O8—C621.425 (6)C51—H510.950
O8—H80.820C52—H520.951
O9—C601.428 (5)C53—C541.396 (7)
O9—C631.442 (6)C53—C581.394 (7)
O10—C611.429 (5)C54—C551.379 (9)
O10—C631.422 (6)C54—H540.950
N11—C181.328 (9)C55—C561.36 (1)
N11—C191.507 (10)C55—H550.951
N11—C221.48 (1)C56—C571.396 (9)
C12—C131.52 (1)C56—H560.950
C12—C171.47 (1)C57—C581.387 (8)
C13—C141.48 (1)C57—H570.950
C13—H13A0.950C58—H580.949
C13—H13B0.950C59—C601.552 (6)
C14—C151.50 (2)C59—C691.527 (6)
C14—H14A0.949C59—C751.529 (6)
C14—H14B0.951C60—C611.550 (6)
C15—C161.49 (1)C60—H600.950
C15—H15A0.951C61—C621.551 (7)
C15—H15B0.950C61—H610.950
C16—C171.344 (10)C62—C811.536 (7)
C16—C181.490 (9)C62—C871.537 (7)
C17—H170.950C63—C641.531 (6)
C19—C201.48 (1)C63—C681.502 (6)
C19—H19A0.950C64—C651.517 (7)
C19—H19B0.951C64—H64A0.950
C20—C211.33 (2)C64—H64B0.950
C20—H200.949C65—C661.508 (8)
C21—H21A0.951C65—H65A0.950
C21—H21B0.950C65—H65B0.950
C22—C231.43 (2)C66—C671.521 (8)
C22—H22A0.949C66—H66A0.950
C22—H22B0.951C66—H66B0.950
C23—C241.49 (4)C67—C681.538 (7)
C23—H23A0.949C67—H67A0.950
C23—H23B0.939C67—H67B0.950
C24—H24A0.955C68—H68A0.950
C24—H24B0.960C68—H68B0.950
C24—H24C0.951C69—C701.379 (6)
C25—C261.539 (6)C69—C741.391 (6)
C25—C351.507 (8)C70—C711.386 (8)
C25—C411.540 (7)C70—H700.950
C26—C271.546 (6)C71—C721.396 (8)
C26—H260.950C71—H710.950
C27—C281.562 (6)C72—C731.362 (9)
C27—H270.950C72—H720.950
C28—C471.513 (6)C73—C741.387 (7)
C28—C531.513 (7)C73—H730.950
C29—C301.532 (7)C74—H740.950
C29—C341.525 (6)C75—C761.409 (6)
C30—C311.528 (7)C75—C801.378 (6)
C30—H30A0.950C76—C771.392 (8)
C30—H30B0.950C76—H760.950
C31—C321.516 (8)C77—C781.360 (8)
C31—H31A0.949C77—H770.950
C31—H31B0.951C78—C791.378 (9)
C32—C331.516 (8)C78—H780.950
C32—H32A0.950C79—C801.400 (8)
C32—H32B0.950C79—H790.950
C33—C341.523 (7)C80—H800.950
C33—H33A0.950C81—C821.391 (7)
C33—H33B0.951C81—C861.379 (7)
C34—H34A0.950C82—C831.406 (9)
C34—H34B0.950C82—H820.950
C35—C361.409 (9)C83—C841.372 (9)
C35—C401.37 (1)C83—H830.950
C36—C371.35 (1)C84—C851.377 (9)
C36—H360.950C84—H840.950
C37—C381.33 (2)C85—C861.404 (8)
C37—H370.949C85—H850.950
C38—C391.40 (2)C86—H860.950
C38—H380.951C87—C881.384 (9)
C39—C401.45 (1)C87—C921.390 (8)
C39—H390.950C88—C891.41 (1)
C40—H400.951C88—H880.950
C41—C421.377 (7)C89—C901.35 (2)
C41—C461.389 (7)C89—H890.950
C42—C431.362 (9)C90—C911.37 (2)
C42—H420.950C90—H900.951
C43—C441.375 (10)C91—C921.39 (1)
C43—H430.950C91—H910.951
C44—C451.361 (9)C92—H920.949
C44—H440.950
C25—O3—H3109.5C28—C47—C52125.3 (4)
C28—O4—H4109.5C48—C47—C52116.6 (4)
C26—O5—C29108.6 (3)C47—C48—C49121.4 (5)
C27—O6—C29109.3 (3)C47—C48—H48119.2
C59—O7—H7109.5C49—C48—H48119.3
C62—O8—H8109.5C48—C49—C50121.0 (5)
C60—O9—C63109.8 (3)C48—C49—H49119.5
C61—O10—C63108.9 (3)C50—C49—H49119.5
C18—N11—C19122.6 (6)C49—C50—C51118.0 (5)
C18—N11—C22119.6 (7)C49—C50—H50121.0
C19—N11—C22117.7 (7)C51—C50—H50121.1
O1—C12—C13121.4 (7)C50—C51—C52122.2 (5)
O1—C12—C17123.0 (6)C50—C51—H51118.9
C13—C12—C17115.5 (6)C52—C51—H51118.9
C12—C13—C14114.6 (7)C47—C52—C51120.9 (5)
C12—C13—H13A108.2C47—C52—H52119.5
C12—C13—H13B108.3C51—C52—H52119.6
C14—C13—H13A108.0C28—C53—C54121.5 (5)
C14—C13—H13B108.1C28—C53—C58120.0 (4)
H13A—C13—H13B109.5C54—C53—C58118.5 (5)
C13—C14—C15113.2 (9)C53—C54—C55119.8 (5)
C13—C14—H14A108.7C53—C54—H54120.1
C13—C14—H14B108.5C55—C54—H54120.1
C15—C14—H14A108.6C54—C55—C56122.4 (6)
C15—C14—H14B108.4C54—C55—H55118.8
H14A—C14—H14B109.5C56—C55—H55118.8
C14—C15—C16112.2 (7)C55—C56—C57118.2 (6)
C14—C15—H15A108.7C55—C56—H56121.0
C14—C15—H15B108.8C57—C56—H56120.9
C16—C15—H15A108.8C56—C57—C58120.6 (6)
C16—C15—H15B108.9C56—C57—H57119.8
H15A—C15—H15B109.4C58—C57—H57119.6
C15—C16—C17123.1 (7)C53—C58—C57120.5 (5)
C15—C16—C18114.1 (6)C53—C58—H58119.8
C17—C16—C18122.0 (6)C57—C58—H58119.8
C12—C17—C16122.2 (6)O7—C59—C60104.9 (3)
C12—C17—H17118.9O7—C59—C69108.8 (3)
C16—C17—H17119.0O7—C59—C75107.8 (3)
O2—C18—N11122.9 (6)C60—C59—C69112.1 (3)
O2—C18—C16118.7 (6)C60—C59—C75112.9 (3)
N11—C18—C16118.3 (5)C69—C59—C75110.1 (3)
N11—C19—C20113.7 (7)O9—C60—C59109.1 (3)
N11—C19—H19A108.5O9—C60—C61104.4 (3)
N11—C19—H19B108.5O9—C60—H60108.6
C20—C19—H19A108.3C59—C60—C61117.1 (3)
C20—C19—H19B108.3C59—C60—H60108.7
H19A—C19—H19B109.4C61—C60—H60108.7
C19—C20—C21121.6 (9)O10—C61—C60102.0 (3)
C19—C20—H20119.1O10—C61—C62109.4 (3)
C21—C20—H20119.2O10—C61—H61108.9
C20—C21—H21A120.0C60—C61—C62118.1 (4)
C20—C21—H21B120.1C60—C61—H61109.0
H21A—C21—H21B119.9C62—C61—H61109.0
N11—C22—C23113 (1)O8—C62—C61107.1 (4)
N11—C22—H22A108.5O8—C62—C81103.6 (4)
N11—C22—H22B108.3O8—C62—C87111.2 (4)
C23—C22—H22A109.1C61—C62—C81112.8 (4)
C23—C22—H22B107.7C61—C62—C87111.9 (4)
H22A—C22—H22B109.4C81—C62—C87109.8 (4)
C22—C23—C24116 (1)O9—C63—O10105.6 (3)
C22—C23—H23A108.4O9—C63—C64109.7 (4)
C22—C23—H23B109.1O9—C63—C68110.0 (4)
C24—C23—H23A105.6O10—C63—C64110.8 (4)
C24—C23—H23B106.6O10—C63—C68108.6 (4)
H23A—C23—H23B110.5C64—C63—C68111.9 (4)
C23—C24—H24A110.4C63—C64—C65111.8 (4)
C23—C24—H24B109.8C63—C64—H64A108.9
C23—C24—H24C110.9C63—C64—H64B108.9
H24A—C24—H24B108.2C65—C64—H64A108.9
H24A—C24—H24C109.0C65—C64—H64B108.9
H24B—C24—H24C108.6H64A—C64—H64B109.4
O3—C25—C26107.8 (4)C64—C65—C66112.1 (5)
O3—C25—C35110.2 (4)C64—C65—H65A108.9
O3—C25—C41103.0 (4)C64—C65—H65B108.8
C26—C25—C35111.0 (4)C66—C65—H65A108.8
C26—C25—C41112.9 (4)C66—C65—H65B108.8
C35—C25—C41111.6 (4)H65A—C65—H65B109.5
O5—C26—C25106.3 (3)C65—C66—C67111.3 (5)
O5—C26—C27101.8 (3)C65—C66—H66A109.0
O5—C26—H26109.8C65—C66—H66B109.0
C25—C26—C27118.6 (4)C67—C66—H66A109.0
C25—C26—H26109.9C67—C66—H66B109.0
C27—C26—H26109.8H66A—C66—H66B109.5
O6—C27—C26103.6 (3)C66—C67—C68110.4 (4)
O6—C27—C28108.5 (3)C66—C67—H67A109.2
O6—C27—H27109.3C66—C67—H67B109.2
C26—C27—C28116.6 (4)C68—C67—H67A109.2
C26—C27—H27109.3C68—C67—H67B109.2
C28—C27—H27109.3H67A—C67—H67B109.5
O4—C28—C27105.4 (3)C63—C68—C67111.8 (4)
O4—C28—C47107.3 (4)C63—C68—H68A108.9
O4—C28—C53108.3 (4)C63—C68—H68B108.9
C27—C28—C47113.6 (4)C67—C68—H68A108.9
C27—C28—C53110.7 (4)C67—C68—H68B108.9
C47—C28—C53111.2 (4)H68A—C68—H68B109.5
O5—C29—O6106.5 (3)C59—C69—C70121.7 (4)
O5—C29—C30108.0 (4)C59—C69—C74119.7 (4)
O5—C29—C34110.0 (4)C70—C69—C74118.6 (4)
O6—C29—C30108.8 (4)C69—C70—C71120.8 (5)
O6—C29—C34110.7 (4)C69—C70—H70119.6
C30—C29—C34112.6 (4)C71—C70—H70119.6
C29—C30—C31110.5 (4)C70—C71—C72120.0 (5)
C29—C30—H30A109.2C70—C71—H71120.0
C29—C30—H30B109.2C72—C71—H71120.0
C31—C30—H30A109.2C71—C72—C73119.5 (5)
C31—C30—H30B109.3C71—C72—H72120.3
H30A—C30—H30B109.5C73—C72—H72120.2
C30—C31—C32111.8 (4)C72—C73—C74120.5 (5)
C30—C31—H31A108.9C72—C73—H73119.8
C30—C31—H31B108.8C74—C73—H73119.7
C32—C31—H31A109.0C69—C74—C73120.7 (5)
C32—C31—H31B108.9C69—C74—H74119.6
H31A—C31—H31B109.5C73—C74—H74119.7
C31—C32—C33110.6 (4)C59—C75—C76116.1 (4)
C31—C32—H32A109.2C59—C75—C80125.4 (4)
C31—C32—H32B109.2C76—C75—C80118.4 (4)
C33—C32—H32A109.2C75—C76—C77120.2 (4)
C33—C32—H32B109.2C75—C76—H76119.9
H32A—C32—H32B109.5C77—C76—H76119.9
C32—C33—C34112.1 (4)C76—C77—C78120.4 (5)
C32—C33—H33A108.8C76—C77—H77119.8
C32—C33—H33B108.7C78—C77—H77119.8
C34—C33—H33A108.9C77—C78—C79120.5 (5)
C34—C33—H33B108.8C77—C78—H78119.8
H33A—C33—H33B109.5C79—C78—H78119.7
C29—C34—C33110.6 (4)C78—C79—C80119.8 (5)
C29—C34—H34A109.2C78—C79—H79120.1
C29—C34—H34B109.2C80—C79—H79120.1
C33—C34—H34A109.2C75—C80—C79120.7 (5)
C33—C34—H34B109.2C75—C80—H80119.7
H34A—C34—H34B109.4C79—C80—H80119.6
C25—C35—C36120.3 (6)C62—C81—C82116.6 (4)
C25—C35—C40120.3 (5)C62—C81—C86124.6 (4)
C36—C35—C40119.4 (6)C82—C81—C86118.5 (5)
C35—C36—C37122.8 (9)C81—C82—C83120.0 (5)
C35—C36—H36118.7C81—C82—H82120.0
C37—C36—H36118.6C83—C82—H82120.0
C36—C37—C38117.8 (9)C82—C83—C84120.8 (6)
C36—C37—H37120.9C82—C83—H83119.6
C38—C37—H37121.3C84—C83—H83119.6
C37—C38—C39124 (1)C83—C84—C85119.4 (5)
C37—C38—H38117.8C83—C84—H84120.3
C39—C38—H38117.7C85—C84—H84120.3
C38—C39—C40116 (1)C84—C85—C86120.0 (5)
C38—C39—H39121.9C84—C85—H85120.0
C40—C39—H39121.7C86—C85—H85120.0
C35—C40—C39119.0 (7)C81—C86—C85121.1 (5)
C35—C40—H40120.5C81—C86—H86119.5
C39—C40—H40120.5C85—C86—H86119.4
C25—C41—C42117.9 (4)C62—C87—C88120.6 (5)
C25—C41—C46124.6 (4)C62—C87—C92121.5 (5)
C42—C41—C46117.4 (5)C88—C87—C92117.9 (6)
C41—C42—C43121.4 (5)C87—C88—C89119.8 (8)
C41—C42—H42119.3C87—C88—H88120.0
C43—C42—H42119.3C89—C88—H88120.2
C42—C43—C44121.2 (6)C88—C89—C90120.8 (9)
C42—C43—H43119.4C88—C89—H89119.7
C44—C43—H43119.4C90—C89—H89119.4
C43—C44—C45118.4 (5)C89—C90—C91120.1 (10)
C43—C44—H44120.8C89—C90—H90120.1
C45—C44—H44120.8C91—C90—H90119.8
C44—C45—C46120.9 (6)C90—C91—C92119.8 (9)
C44—C45—H45119.5C90—C91—H91120.2
C46—C45—H45119.6C92—C91—H91120.0
C41—C46—C45120.6 (5)C87—C92—C91121.5 (6)
C41—C46—H46119.7C87—C92—H92119.2
C45—C46—H46119.8C91—C92—H92119.3
C28—C47—C48118.0 (4)
N11—C18—C16—C1782.8 (9)C18—N11—C19—C20103.9 (9)
N11—C19—C20—C21138.6 (10)C18—N11—C22—C23108 (1)
N11—C22—C23—C2446 (2)C25—C26—C27—C2896.4 (5)
C16—C18—N11—C193.0 (10)C59—C60—C61—C6294.6 (4)
C16—C18—N11—C22179.2 (8)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—H3···O40.821.872.683 (5)169
O4—H4···O20.821.942.736 (6)165
O7—H7···O10.822.012.825 (5)173
O8—H8···O70.821.872.682 (4)168

Experimental details

Crystal data
Chemical formula2C34H34O4·C13H19NO2
Mr1234.58
Crystal system, space groupMonoclinic, P21
Temperature (K)248
a, b, c (Å)10.4041 (16), 34.308 (4), 9.5158 (12)
β (°) 93.338 (11)
V3)3390.8 (8)
Z2
Radiation typeCu Kα
µ (mm1)0.62
Crystal size (mm)0.8 × 0.2 × 0.05
Data collection
DiffractometerRigaku AFC-7R
diffractometer
Absorption correctionIntegration
(Coppens et al., 1965)
Tmin, Tmax0.831, 0.969
No. of measured, independent and
observed [I > 2σ(I)] reflections
6683, 5806, 4617
Rint0.081
(sin θ/λ)max1)0.588
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.062, 0.172, 1.02
No. of reflections5806
No. of parameters833
No. of restraints?
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.27, 0.32

Computer programs: WinAFC Diffractometer Control Software (Rigaku, 1999), WinAFC Diffractometer Control Software, TEXSAN (Molecular Structure Corporation, 2001), SIR92 (Altomare et al., 1994), SHELXL97 (Sheldrick, 1997), ORTEPII (Johnson, 1976), TEXSAN.

Selected geometric parameters (Å, º) top
O1—C121.218 (8)C16—C171.344 (10)
O2—C181.216 (7)C16—C181.490 (9)
N11—C181.328 (9)C19—C201.48 (1)
N11—C191.507 (10)C20—C211.33 (2)
C12—C171.47 (1)
N11—C19—C20113.7 (7)C19—C20—C21121.6 (9)
N11—C18—C16—C1782.8 (9)C18—N11—C19—C20103.9 (9)
N11—C19—C20—C21138.6 (10)C18—N11—C22—C23108 (1)
N11—C22—C23—C2446 (2)C25—C26—C27—C2896.4 (5)
C16—C18—N11—C193.0 (10)C59—C60—C61—C6294.6 (4)
C16—C18—N11—C22179.2 (8)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—H3···O40.821.872.683 (5)169
O4—H4···O20.821.942.736 (6)165
O7—H7···O10.822.012.825 (5)173
O8—H8···O70.821.872.682 (4)168
 

Subscribe to Acta Crystallographica Section E: Crystallographic Communications

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