organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

3,3,9,9-Tetra­phenyl-2,4,8,10-tetra­oxa­spiro­[5.5]undeca­ne

aKey Laboratory of Fine Chemical Engineering, Changzhou University, Changzhou 213164, Jiangsu, People's Republic of China
*Correspondence e-mail: chemlzy@yahoo.com.cn

(Received 8 October 2010; accepted 27 October 2010; online 31 October 2010)

In the title compound, C31H28O4, the asymmetric unit contains two crystallographically independent mol­ecules. In these two mol­ecules, the four dihedral angles between each pair of phenyl rings on the same C atoms are 75.4 (1), 83.0 (1), 85.0 (1) and 80.4 (2)°. All of the nonplanar six-membered heterocycles adopt chair conformations. Inter­molecular C—H⋯π and weak C—H⋯O inter­actions link the mol­ecules and are effective in the stabilization of the crystal structure.

Related literature

For general background to spiranes, see: Cismaş et al. (2005[Cismaş, C., Terec, A., Mager, S. & Grosu, I. (2005). Curr. Org. Chem. 9, 1287-1314.]); Mihiş et al. (2008[Mihiş, A., Condamine, E., Bogdan, E., Terec, A., Kurtán, T. & Grosu, I. (2008). Molecules, 13, 2848-2858.]); Sun et al. (2010[Sun, X., Yu, S.-L., Li, Z.-Y. & Yang, Y. (2010). J. Mol. Struct. 973, 152-156.]).

[Scheme 1]

Experimental

Crystal data
  • C31H28O4

  • Mr = 464.53

  • Triclinic, [P \overline 1]

  • a = 13.509 (3) Å

  • b = 13.790 (3) Å

  • c = 15.626 (5) Å

  • α = 102.327 (7)°

  • β = 104.199 (6)°

  • γ = 112.170 (4)°

  • V = 2456.8 (11) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.08 mm−1

  • T = 295 K

  • 0.26 × 0.22 × 0.20 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2000[Bruker (2000). SAINT, SMART and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.979, Tmax = 0.984

  • 13730 measured reflections

  • 8545 independent reflections

  • 5355 reflections with I > 2σ(I)

  • Rint = 0.026

Refinement
  • R[F2 > 2σ(F2)] = 0.053

  • wR(F2) = 0.196

  • S = 1.01

  • 8545 reflections

  • 631 parameters

  • 1 restraint

  • H-atom parameters constrained

  • Δρmax = 0.23 e Å−3

  • Δρmin = −0.28 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C38–C43 and C7–C12 rings, respectively.

D—H⋯A D—H H⋯A DA D—H⋯A
C9—H9⋯Cg1i 0.93 2.83 3.722 (2) 161
C30—H30⋯Cg2ii 0.93 2.84 3.523 (3) 131
C3—H3A⋯O6ii 0.97 2.53 3.436 (3) 156
Symmetry codes: (i) -x+1, -y, -z+1; (ii) -x+1, -y+1, -z+1.

Data collection: SMART (Bruker, 2000[Bruker (2000). SAINT, SMART and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2000[Bruker (2000). SAINT, SMART and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information


Comment top

Owing to the characteristic axial and helical chirality, the stereochemistry of spiranes with six-membered rings has been extensively studied (Cismaş et al., 2005). In the past three decades, most of these investigations were carried out with spiranes containing 1,3-dioxane units (Mihiş et al., 2008; Sun et al., 2010). We herein present the structure of 3,3,9,9-tetraphenyl-2,4,8,10-tetraoxaspiro[5.5]undecane (I).

In the crystal structure of (I), the asymmetric unit contains two crystallographically independent molecules (Fig. 1). In these two molecules, the four dihedral angles between each two phenyl rings on the same C atoms are all different. In one molecule, the dihedral angles formed by the phenyl rings (C7–C12) and (C13–C18) are 75.4 (1)° and 83.0 (1)° for the phenyl rings (C20–C25) and (C26–C31). In the other molecule, the dihedral angles between the phenyl rings (C38–C43) and (C44–C49) are 85.0 (1)° and 80.4 (2)° for the phenyl rings (C51–C56) and (C57–C62). The four nonplanar six-membered heterocycles [(O1/O2/C1–C3/C6), (O3/O4/C2/C4/C5/C19), (O5/O6/C32–C34/C37) and (O7/O8/C33/C35/C36/C50)] all adopt chair conformations.

Intermolecular C—H···π and weak C—H···O interactions link the molecules and are effective in the stabilization of the crystal structure (Table 1).

Related literature top

For general background to spiranes, see: Cismaş et al. (2005); Mihiş et al. (2008); Sun et al. (2010).

Experimental top

To a solution of benzophenone (7.3 mmol, 1.33 g) and pentaerythritol (4 mmol, 0.54 g) in toluene (30 ml), phosphotungstic acid (30 mg) as catalyst was added, respectively. The mixtures were refluxed for 4 h to complete the reaction. After reaction, the solvent was evaporated under vacuum and the resulting solid was washed with 5% sodium bicarboinate (20 ml) and 50% ethanol (20 ml). The product recrystallized from ethanol to afford a white solid (71% yield, m.p. 436–437 K). Single crystals suitable for X-ray diffraction were also obtained by evaporation of an ethanol solution.

Refinement top

All the H atoms were placed in geometrically idealized positions and constrained to ride on their parent atoms, with C—H distances of 0.93–0.97 Å, and with Uiso(H) = 1.2Ueq(C).

Structure description top

Owing to the characteristic axial and helical chirality, the stereochemistry of spiranes with six-membered rings has been extensively studied (Cismaş et al., 2005). In the past three decades, most of these investigations were carried out with spiranes containing 1,3-dioxane units (Mihiş et al., 2008; Sun et al., 2010). We herein present the structure of 3,3,9,9-tetraphenyl-2,4,8,10-tetraoxaspiro[5.5]undecane (I).

In the crystal structure of (I), the asymmetric unit contains two crystallographically independent molecules (Fig. 1). In these two molecules, the four dihedral angles between each two phenyl rings on the same C atoms are all different. In one molecule, the dihedral angles formed by the phenyl rings (C7–C12) and (C13–C18) are 75.4 (1)° and 83.0 (1)° for the phenyl rings (C20–C25) and (C26–C31). In the other molecule, the dihedral angles between the phenyl rings (C38–C43) and (C44–C49) are 85.0 (1)° and 80.4 (2)° for the phenyl rings (C51–C56) and (C57–C62). The four nonplanar six-membered heterocycles [(O1/O2/C1–C3/C6), (O3/O4/C2/C4/C5/C19), (O5/O6/C32–C34/C37) and (O7/O8/C33/C35/C36/C50)] all adopt chair conformations.

Intermolecular C—H···π and weak C—H···O interactions link the molecules and are effective in the stabilization of the crystal structure (Table 1).

For general background to spiranes, see: Cismaş et al. (2005); Mihiş et al. (2008); Sun et al. (2010).

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound (I). Displacement ellipsoids are drawn at the 30% probability level. All H atoms have been omitted for clarity.
3,3,9,9-Tetraphenyl-2,4,8,10-tetraoxaspiro[5.5]undecane top
Crystal data top
C31H28O4Z = 4
Mr = 464.53F(000) = 984
Triclinic, P1Dx = 1.256 Mg m3
Hall symbol: -P 1Melting point = 436–437 K
a = 13.509 (3) ÅMo Kα radiation, λ = 0.71073 Å
b = 13.790 (3) ÅCell parameters from 13730 reflections
c = 15.626 (5) Åθ = 2.6–24.8°
α = 102.327 (7)°µ = 0.08 mm1
β = 104.199 (6)°T = 295 K
γ = 112.170 (4)°Prism, colourless
V = 2456.8 (11) Å30.26 × 0.22 × 0.20 mm
Data collection top
Bruker APEXII CCD
diffractometer
8545 independent reflections
Radiation source: fine-focus sealed tube5355 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.026
φ and ω scansθmax = 25.0°, θmin = 1.4°
Absorption correction: multi-scan
(SADABS; Bruker, 2000)
h = 1416
Tmin = 0.979, Tmax = 0.984k = 1615
13730 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)] = 0.053Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.196H-atom parameters constrained
S = 1.01 w = 1/[σ2(Fo2) + (0.102P)2 + 0.5251P]
where P = (Fo2 + 2Fc2)/3
8545 reflections(Δ/σ)max < 0.001
631 parametersΔρmax = 0.23 e Å3
1 restraintΔρmin = 0.28 e Å3
Crystal data top
C31H28O4γ = 112.170 (4)°
Mr = 464.53V = 2456.8 (11) Å3
Triclinic, P1Z = 4
a = 13.509 (3) ÅMo Kα radiation
b = 13.790 (3) ŵ = 0.08 mm1
c = 15.626 (5) ÅT = 295 K
α = 102.327 (7)°0.26 × 0.22 × 0.20 mm
β = 104.199 (6)°
Data collection top
Bruker APEXII CCD
diffractometer
8545 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2000)
5355 reflections with I > 2σ(I)
Tmin = 0.979, Tmax = 0.984Rint = 0.026
13730 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0531 restraint
wR(F2) = 0.196H-atom parameters constrained
S = 1.01Δρmax = 0.23 e Å3
8545 reflectionsΔρmin = 0.28 e Å3
631 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
C10.5250 (2)0.5283 (2)0.82950 (19)0.0472 (7)
H1A0.54000.56580.89470.057*
H1B0.44570.47180.80130.057*
C20.5446 (2)0.6118 (2)0.77849 (17)0.0406 (6)
C30.6715 (2)0.6927 (2)0.82180 (18)0.0456 (7)
H3A0.68880.74650.78970.055*
H3B0.69100.73290.88740.055*
C40.4723 (2)0.6725 (2)0.78827 (18)0.0483 (7)
H4A0.48810.70690.85430.058*
H4B0.49250.73100.76110.058*
C50.5090 (2)0.5550 (2)0.67320 (17)0.0436 (6)
H5A0.52780.61100.64340.052*
H5B0.55090.51280.66260.052*
C60.7171 (2)0.5520 (2)0.85862 (17)0.0403 (6)
C70.7748 (2)0.4827 (2)0.82801 (17)0.0439 (6)
C80.7288 (3)0.3705 (2)0.81755 (19)0.0546 (7)
H80.66180.33730.82910.066*
C90.7821 (3)0.3071 (3)0.7899 (2)0.0638 (9)
H90.75140.23220.78400.077*
C100.8781 (3)0.3544 (3)0.7717 (2)0.0764 (11)
H100.91240.31120.75190.092*
C110.9263 (3)0.4654 (3)0.7817 (3)0.0847 (12)
H110.99320.49740.76970.102*
C120.8742 (2)0.5292 (3)0.8100 (2)0.0671 (9)
H120.90660.60440.81700.080*
C130.7661 (2)0.6058 (2)0.96562 (17)0.0417 (6)
C140.7190 (3)0.5509 (3)1.0212 (2)0.0544 (7)
H140.65220.48380.99320.065*
C150.7706 (3)0.5954 (3)1.1181 (2)0.0705 (10)
H150.73820.55821.15490.085*
C160.8688 (3)0.6935 (4)1.1597 (2)0.0752 (11)
H160.90280.72331.22480.090*
C170.9178 (3)0.7485 (3)1.1057 (2)0.0685 (9)
H170.98550.81471.13420.082*
C180.8662 (2)0.7051 (2)1.00877 (19)0.0525 (7)
H180.89900.74280.97240.063*
C190.3205 (2)0.5361 (2)0.64462 (17)0.0419 (6)
C200.1985 (2)0.4453 (2)0.61579 (17)0.0426 (6)
C210.1780 (2)0.3370 (2)0.60770 (19)0.0501 (7)
H210.23860.31900.61850.060*
C220.0671 (3)0.2551 (3)0.5835 (2)0.0593 (8)
H220.05390.18240.57790.071*
C230.0232 (3)0.2806 (3)0.5677 (2)0.0604 (8)
H230.09740.22540.55140.072*
C240.0032 (3)0.3877 (3)0.5761 (3)0.0725 (10)
H240.06420.40530.56580.087*
C250.1072 (2)0.4705 (3)0.5999 (2)0.0638 (8)
H250.11990.54300.60510.077*
C260.3259 (2)0.6120 (2)0.58554 (18)0.0437 (6)
C270.3225 (2)0.7116 (2)0.6153 (2)0.0570 (8)
H270.32210.73700.67530.068*
C280.3198 (3)0.7751 (3)0.5571 (3)0.0719 (10)
H280.31680.84200.57790.086*
C290.3214 (3)0.7383 (4)0.4689 (3)0.0819 (12)
H290.32080.78090.43010.098*
C300.3240 (3)0.6396 (4)0.4381 (2)0.0742 (10)
H300.32380.61450.37780.089*
C310.3270 (2)0.5760 (3)0.49551 (19)0.0581 (8)
H310.32960.50910.47390.070*
C320.1745 (2)0.2197 (2)0.34555 (18)0.0433 (6)
H32A0.18800.28260.32370.052*
H32B0.18580.24550.41160.052*
C330.0521 (2)0.1305 (2)0.29122 (17)0.0445 (6)
C340.0392 (2)0.0302 (2)0.32237 (19)0.0501 (7)
H34A0.04500.04880.38750.060*
H34B0.03590.03150.28480.060*
C350.0254 (2)0.0994 (2)0.18545 (17)0.0467 (7)
H35A0.04290.16600.16850.056*
H35B0.07310.06670.16860.056*
C360.0318 (2)0.1720 (2)0.31093 (18)0.0487 (7)
H36A0.02100.18870.37700.058*
H36B0.01680.24010.29680.058*
C370.2397 (2)0.0832 (2)0.36191 (17)0.0420 (6)
C380.3157 (2)0.0397 (2)0.32644 (17)0.0429 (6)
C390.3208 (3)0.0369 (2)0.2383 (2)0.0599 (8)
H390.27630.06040.20080.072*
C400.3903 (3)0.0001 (3)0.2057 (2)0.0724 (10)
H400.39230.00100.14640.087*
C410.4571 (3)0.0350 (3)0.2597 (2)0.0697 (9)
H410.50560.05800.23800.084*
C420.4512 (3)0.0357 (3)0.3459 (2)0.0676 (9)
H420.49370.06200.38200.081*
C430.3824 (3)0.0026 (2)0.3794 (2)0.0553 (7)
H430.38090.00360.43870.066*
C440.2730 (2)0.1143 (2)0.46846 (17)0.0416 (6)
C450.2173 (2)0.0406 (3)0.5081 (2)0.0556 (8)
H450.15420.02700.46980.067*
C460.2547 (3)0.0667 (3)0.6047 (2)0.0718 (10)
H460.21570.01760.63110.086*
C470.3499 (3)0.1655 (3)0.6616 (2)0.0682 (9)
H470.37560.18270.72640.082*
C480.4066 (3)0.2383 (3)0.6225 (2)0.0601 (8)
H480.47100.30480.66090.072*
C490.3683 (2)0.2132 (2)0.52624 (18)0.0481 (7)
H490.40680.26320.50020.058*
C500.1712 (2)0.0584 (2)0.15671 (17)0.0440 (6)
C510.2886 (2)0.0445 (2)0.11423 (17)0.0404 (6)
C520.2966 (3)0.1480 (2)0.1128 (2)0.0568 (8)
H520.23020.15520.13500.068*
C530.4011 (3)0.2399 (3)0.0791 (2)0.0611 (8)
H530.40500.30870.07910.073*
C540.4999 (3)0.2311 (3)0.0454 (2)0.0550 (7)
H540.57060.29400.02150.066*
C550.4943 (3)0.1302 (3)0.0469 (2)0.0666 (9)
H550.56130.12370.02540.080*
C560.3890 (2)0.0370 (3)0.0805 (2)0.0584 (8)
H560.38580.03150.08040.070*
C570.1705 (2)0.1521 (2)0.12028 (17)0.0431 (6)
C580.1490 (2)0.1561 (2)0.03813 (19)0.0498 (7)
H580.13060.10370.00720.060*
C590.1551 (3)0.2387 (3)0.0022 (2)0.0657 (8)
H590.14110.24070.05290.079*
C600.1812 (3)0.3161 (3)0.0467 (2)0.0653 (8)
H600.18290.37210.02300.078*
C610.2053 (3)0.3124 (3)0.1271 (2)0.0615 (8)
H610.22610.36390.15610.074*
C620.1984 (2)0.2318 (2)0.1642 (2)0.0517 (7)
H620.21270.23080.21940.062*
O10.59843 (14)0.47657 (14)0.82486 (12)0.0465 (5)
O20.73780 (14)0.63359 (15)0.81425 (12)0.0444 (4)
O30.38922 (14)0.48245 (15)0.63265 (12)0.0457 (5)
O40.35231 (15)0.59668 (15)0.74173 (11)0.0466 (5)
O50.12532 (15)0.00276 (14)0.31258 (12)0.0490 (5)
O60.25474 (14)0.17839 (14)0.33426 (12)0.0419 (4)
O70.09301 (15)0.02172 (15)0.13444 (12)0.0459 (5)
O80.14763 (15)0.09070 (15)0.25580 (11)0.0481 (5)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0328 (14)0.0589 (17)0.0487 (16)0.0171 (13)0.0154 (12)0.0224 (13)
C20.0362 (14)0.0513 (16)0.0370 (14)0.0206 (12)0.0138 (11)0.0181 (12)
C30.0413 (15)0.0506 (16)0.0435 (15)0.0165 (13)0.0140 (12)0.0227 (12)
C40.0439 (16)0.0586 (17)0.0359 (14)0.0226 (14)0.0091 (12)0.0113 (12)
C50.0361 (15)0.0568 (17)0.0447 (15)0.0252 (13)0.0170 (12)0.0196 (12)
C60.0309 (14)0.0481 (15)0.0375 (14)0.0125 (12)0.0100 (11)0.0190 (11)
C70.0372 (15)0.0512 (17)0.0349 (14)0.0183 (13)0.0063 (11)0.0100 (12)
C80.0625 (19)0.063 (2)0.0440 (16)0.0314 (16)0.0175 (14)0.0240 (14)
C90.083 (3)0.064 (2)0.0513 (18)0.0458 (19)0.0152 (17)0.0192 (15)
C100.063 (2)0.087 (3)0.067 (2)0.051 (2)0.0045 (17)0.0031 (19)
C110.0421 (19)0.084 (3)0.098 (3)0.0208 (19)0.0225 (18)0.008 (2)
C120.0393 (17)0.060 (2)0.080 (2)0.0125 (15)0.0205 (15)0.0016 (16)
C130.0407 (15)0.0525 (16)0.0403 (14)0.0277 (13)0.0149 (12)0.0187 (12)
C140.0621 (19)0.0673 (19)0.0567 (18)0.0411 (16)0.0285 (15)0.0335 (15)
C150.092 (3)0.108 (3)0.056 (2)0.072 (3)0.040 (2)0.047 (2)
C160.085 (3)0.120 (3)0.0393 (17)0.074 (3)0.0155 (18)0.0181 (19)
C170.055 (2)0.085 (2)0.0463 (18)0.0338 (18)0.0028 (15)0.0015 (16)
C180.0445 (17)0.0606 (18)0.0441 (16)0.0211 (15)0.0115 (13)0.0126 (13)
C190.0391 (15)0.0537 (16)0.0356 (13)0.0237 (13)0.0153 (11)0.0131 (11)
C200.0413 (15)0.0524 (17)0.0374 (14)0.0233 (13)0.0151 (11)0.0167 (12)
C210.0472 (17)0.0583 (18)0.0535 (17)0.0306 (15)0.0200 (13)0.0208 (14)
C220.0523 (19)0.0568 (19)0.0614 (19)0.0178 (16)0.0198 (15)0.0199 (15)
C230.0436 (18)0.065 (2)0.064 (2)0.0179 (16)0.0193 (14)0.0200 (16)
C240.0417 (19)0.086 (3)0.098 (3)0.0330 (18)0.0246 (17)0.039 (2)
C250.0396 (17)0.067 (2)0.094 (2)0.0270 (16)0.0272 (16)0.0341 (18)
C260.0317 (14)0.0541 (17)0.0421 (15)0.0168 (12)0.0107 (11)0.0188 (12)
C270.0503 (18)0.0587 (19)0.0546 (18)0.0233 (15)0.0085 (14)0.0200 (15)
C280.0496 (19)0.065 (2)0.087 (3)0.0193 (16)0.0035 (17)0.0360 (19)
C290.056 (2)0.089 (3)0.075 (3)0.006 (2)0.0052 (18)0.052 (2)
C300.051 (2)0.109 (3)0.0482 (19)0.018 (2)0.0123 (15)0.040 (2)
C310.0486 (18)0.077 (2)0.0415 (16)0.0223 (16)0.0139 (13)0.0220 (14)
C320.0441 (16)0.0445 (15)0.0464 (15)0.0224 (13)0.0154 (12)0.0214 (12)
C330.0438 (15)0.0530 (16)0.0360 (14)0.0201 (13)0.0121 (12)0.0197 (12)
C340.0392 (16)0.0552 (17)0.0470 (16)0.0134 (13)0.0097 (12)0.0225 (13)
C350.0450 (16)0.0613 (18)0.0394 (14)0.0263 (14)0.0167 (12)0.0218 (13)
C360.0452 (16)0.0615 (18)0.0358 (14)0.0223 (14)0.0129 (12)0.0153 (12)
C370.0365 (14)0.0384 (14)0.0429 (14)0.0100 (12)0.0078 (11)0.0195 (11)
C380.0412 (15)0.0386 (14)0.0413 (15)0.0130 (12)0.0106 (12)0.0135 (11)
C390.081 (2)0.0571 (19)0.0539 (18)0.0398 (17)0.0258 (16)0.0251 (14)
C400.094 (3)0.071 (2)0.058 (2)0.038 (2)0.0380 (19)0.0191 (17)
C410.061 (2)0.079 (2)0.068 (2)0.0341 (19)0.0256 (17)0.0147 (18)
C420.065 (2)0.075 (2)0.059 (2)0.0405 (18)0.0102 (16)0.0132 (16)
C430.0576 (19)0.0617 (19)0.0458 (16)0.0298 (16)0.0133 (14)0.0175 (14)
C440.0391 (15)0.0480 (16)0.0392 (14)0.0198 (13)0.0126 (11)0.0195 (12)
C450.0469 (17)0.0644 (19)0.0616 (19)0.0238 (15)0.0182 (14)0.0372 (15)
C460.072 (2)0.114 (3)0.071 (2)0.056 (2)0.0407 (19)0.063 (2)
C470.077 (2)0.104 (3)0.0431 (17)0.060 (2)0.0207 (17)0.0271 (18)
C480.061 (2)0.070 (2)0.0457 (17)0.0386 (17)0.0067 (14)0.0117 (15)
C490.0488 (17)0.0480 (16)0.0435 (15)0.0204 (14)0.0124 (12)0.0158 (12)
C500.0434 (15)0.0604 (18)0.0342 (13)0.0269 (14)0.0176 (12)0.0170 (12)
C510.0389 (15)0.0508 (16)0.0394 (14)0.0242 (13)0.0171 (11)0.0194 (12)
C520.0471 (18)0.060 (2)0.0646 (19)0.0289 (16)0.0163 (14)0.0202 (15)
C530.069 (2)0.0461 (17)0.065 (2)0.0276 (17)0.0197 (16)0.0173 (14)
C540.0500 (18)0.0530 (18)0.0535 (17)0.0174 (15)0.0172 (14)0.0151 (14)
C550.0443 (18)0.068 (2)0.080 (2)0.0214 (16)0.0124 (16)0.0298 (17)
C560.0432 (17)0.0532 (18)0.081 (2)0.0244 (15)0.0169 (15)0.0282 (16)
C570.0369 (15)0.0509 (16)0.0372 (14)0.0164 (13)0.0101 (11)0.0176 (12)
C580.0445 (16)0.0705 (19)0.0444 (15)0.0319 (15)0.0171 (12)0.0260 (14)
C590.061 (2)0.086 (2)0.0522 (18)0.0287 (18)0.0182 (15)0.0382 (16)
C600.0502 (19)0.065 (2)0.080 (2)0.0230 (16)0.0130 (16)0.0404 (17)
C610.0511 (19)0.0553 (19)0.073 (2)0.0254 (15)0.0137 (16)0.0206 (16)
C620.0472 (17)0.0599 (18)0.0529 (17)0.0292 (15)0.0182 (13)0.0187 (14)
O10.0319 (10)0.0497 (11)0.0537 (11)0.0141 (9)0.0122 (8)0.0218 (9)
O20.0371 (10)0.0552 (11)0.0443 (10)0.0183 (9)0.0163 (8)0.0264 (8)
O30.0372 (10)0.0539 (11)0.0467 (10)0.0242 (9)0.0140 (8)0.0128 (8)
O40.0421 (11)0.0633 (12)0.0353 (9)0.0256 (9)0.0153 (8)0.0137 (8)
O50.0378 (10)0.0422 (10)0.0499 (11)0.0090 (9)0.0044 (8)0.0138 (8)
O60.0394 (10)0.0444 (10)0.0456 (10)0.0186 (8)0.0151 (8)0.0232 (8)
O70.0391 (10)0.0592 (12)0.0405 (10)0.0248 (9)0.0139 (8)0.0150 (8)
O80.0446 (11)0.0642 (12)0.0342 (10)0.0213 (10)0.0160 (8)0.0187 (8)
Geometric parameters (Å, º) top
C1—O11.430 (3)C32—O61.432 (3)
C1—C21.515 (4)C32—C331.516 (4)
C1—H1A0.9700C32—H32A0.9700
C1—H1B0.9700C32—H32B0.9700
C2—C31.519 (3)C33—C361.514 (4)
C2—C41.521 (4)C33—C341.526 (4)
C2—C51.526 (3)C33—C351.528 (3)
C3—O21.429 (3)C34—O51.428 (3)
C3—H3A0.9700C34—H34A0.9700
C3—H3B0.9700C34—H34B0.9700
C4—O41.438 (3)C35—O71.434 (3)
C4—H4A0.9700C35—H35A0.9700
C4—H4B0.9700C35—H35B0.9700
C5—O31.423 (3)C36—O81.432 (3)
C5—H5A0.9700C36—H36A0.9700
C5—H5B0.9700C36—H36B0.9700
C6—O21.420 (3)C37—O51.425 (3)
C6—O11.421 (3)C37—O61.427 (3)
C6—C71.517 (4)C37—C381.523 (4)
C6—C131.530 (3)C37—C441.530 (3)
C7—C121.380 (4)C38—C431.386 (4)
C7—C81.387 (4)C38—C391.388 (4)
C8—C91.390 (4)C39—C401.373 (4)
C8—H80.9300C39—H390.9300
C9—C101.345 (5)C40—C411.375 (5)
C9—H90.9300C40—H400.9300
C10—C111.374 (5)C41—C421.370 (4)
C10—H100.9300C41—H410.9300
C11—C121.386 (5)C42—C431.381 (4)
C11—H110.9300C42—H420.9300
C12—H120.9300C43—H430.9300
C13—C181.385 (4)C44—C451.380 (4)
C13—C141.385 (4)C44—C491.383 (4)
C14—C151.386 (4)C45—C461.385 (4)
C14—H140.9300C45—H450.9300
C15—C161.364 (5)C46—C471.378 (5)
C15—H150.9300C46—H460.9300
C16—C171.377 (5)C47—C481.370 (5)
C16—H160.9300C47—H470.9300
C17—C181.384 (4)C48—C491.383 (4)
C17—H170.9300C48—H480.9300
C18—H180.9300C49—H490.9300
C19—O31.410 (3)C50—O71.415 (3)
C19—O41.433 (3)C50—O81.433 (3)
C19—C201.524 (4)C50—C571.517 (4)
C19—C261.531 (4)C50—C511.534 (4)
C20—C211.383 (4)C51—C561.381 (4)
C20—C251.383 (4)C51—C521.385 (4)
C21—C221.387 (4)C52—C531.370 (4)
C21—H210.9300C52—H520.9300
C22—C231.373 (4)C53—C541.371 (4)
C22—H220.9300C53—H530.9300
C23—C241.369 (4)C54—C551.360 (4)
C23—H230.9300C54—H540.9300
C24—C251.389 (4)C55—C561.385 (4)
C24—H240.9300C55—H550.9300
C25—H250.9300C56—H560.9300
C26—C271.375 (4)C57—C581.391 (4)
C26—C311.394 (4)C57—C621.393 (4)
C27—C281.395 (4)C58—C591.392 (4)
C27—H270.9300C58—H580.9300
C28—C291.372 (5)C59—C601.355 (5)
C28—H280.9300C59—H590.9300
C29—C301.361 (5)C60—C611.378 (4)
C29—H290.9300C60—H600.9300
C30—C311.385 (4)C61—C621.381 (4)
C30—H300.9300C61—H610.9300
C31—H310.9300C62—H620.9300
O1—C1—C2110.7 (2)C33—C32—H32B109.4
O1—C1—H1A109.5H32A—C32—H32B108.0
C2—C1—H1A109.5C36—C33—C32110.7 (2)
O1—C1—H1B109.5C36—C33—C34110.7 (2)
C2—C1—H1B109.5C32—C33—C34106.9 (2)
H1A—C1—H1B108.1C36—C33—C35106.4 (2)
C1—C2—C3106.6 (2)C32—C33—C35111.1 (2)
C1—C2—C4111.1 (2)C34—C33—C35111.0 (2)
C3—C2—C4110.9 (2)O5—C34—C33111.1 (2)
C1—C2—C5111.7 (2)O5—C34—H34A109.4
C3—C2—C5110.9 (2)C33—C34—H34A109.4
C4—C2—C5105.8 (2)O5—C34—H34B109.4
O2—C3—C2110.0 (2)C33—C34—H34B109.4
O2—C3—H3A109.7H34A—C34—H34B108.0
C2—C3—H3A109.7O7—C35—C33110.8 (2)
O2—C3—H3B109.7O7—C35—H35A109.5
C2—C3—H3B109.7C33—C35—H35A109.5
H3A—C3—H3B108.2O7—C35—H35B109.5
O4—C4—C2110.7 (2)C33—C35—H35B109.5
O4—C4—H4A109.5H35A—C35—H35B108.1
C2—C4—H4A109.5O8—C36—C33111.2 (2)
O4—C4—H4B109.5O8—C36—H36A109.4
C2—C4—H4B109.5C33—C36—H36A109.4
H4A—C4—H4B108.1O8—C36—H36B109.4
O3—C5—C2110.47 (19)C33—C36—H36B109.4
O3—C5—H5A109.6H36A—C36—H36B108.0
C2—C5—H5A109.6O5—C37—O6110.10 (19)
O3—C5—H5B109.6O5—C37—C38105.9 (2)
C2—C5—H5B109.6O6—C37—C38105.07 (19)
H5A—C5—H5B108.1O5—C37—C44112.3 (2)
O2—C6—O1111.09 (19)O6—C37—C44111.0 (2)
O2—C6—C7106.6 (2)C38—C37—C44112.1 (2)
O1—C6—C7105.5 (2)C43—C38—C39117.3 (3)
O2—C6—C13111.4 (2)C43—C38—C37122.5 (2)
O1—C6—C13111.83 (19)C39—C38—C37120.2 (2)
C7—C6—C13110.1 (2)C40—C39—C38121.2 (3)
C12—C7—C8118.3 (3)C40—C39—H39119.4
C12—C7—C6121.1 (3)C38—C39—H39119.4
C8—C7—C6120.6 (2)C39—C40—C41120.7 (3)
C7—C8—C9120.5 (3)C39—C40—H40119.7
C7—C8—H8119.7C41—C40—H40119.7
C9—C8—H8119.7C42—C41—C40119.1 (3)
C10—C9—C8119.9 (3)C42—C41—H41120.4
C10—C9—H9120.0C40—C41—H41120.4
C8—C9—H9120.0C41—C42—C43120.2 (3)
C9—C10—C11121.1 (3)C41—C42—H42119.9
C9—C10—H10119.4C43—C42—H42119.9
C11—C10—H10119.4C42—C43—C38121.4 (3)
C10—C11—C12119.3 (3)C42—C43—H43119.3
C10—C11—H11120.4C38—C43—H43119.3
C12—C11—H11120.4C45—C44—C49119.1 (2)
C7—C12—C11120.9 (3)C45—C44—C37121.2 (2)
C7—C12—H12119.6C49—C44—C37119.3 (2)
C11—C12—H12119.6C44—C45—C46120.3 (3)
C18—C13—C14118.8 (3)C44—C45—H45119.8
C18—C13—C6120.0 (2)C46—C45—H45119.8
C14—C13—C6120.9 (3)C47—C46—C45120.0 (3)
C13—C14—C15120.4 (3)C47—C46—H46120.0
C13—C14—H14119.8C45—C46—H46120.0
C15—C14—H14119.8C48—C47—C46119.9 (3)
C16—C15—C14120.1 (3)C48—C47—H47120.0
C16—C15—H15119.9C46—C47—H47120.0
C14—C15—H15119.9C47—C48—C49120.2 (3)
C15—C16—C17120.3 (3)C47—C48—H48119.9
C15—C16—H16119.9C49—C48—H48119.9
C17—C16—H16119.9C48—C49—C44120.4 (3)
C16—C17—C18119.9 (3)C48—C49—H49119.8
C16—C17—H17120.0C44—C49—H49119.8
C18—C17—H17120.0O7—C50—O8110.7 (2)
C17—C18—C13120.4 (3)O7—C50—C57111.2 (2)
C17—C18—H18119.8O8—C50—C57111.4 (2)
C13—C18—H18119.8O7—C50—C51106.1 (2)
O3—C19—O4111.13 (19)O8—C50—C51104.26 (19)
O3—C19—C20107.2 (2)C57—C50—C51112.8 (2)
O4—C19—C20105.10 (19)C56—C51—C52118.0 (3)
O3—C19—C26110.9 (2)C56—C51—C50121.9 (2)
O4—C19—C26111.2 (2)C52—C51—C50120.1 (2)
C20—C19—C26111.2 (2)C53—C52—C51120.9 (3)
C21—C20—C25119.1 (3)C53—C52—H52119.5
C21—C20—C19120.4 (2)C51—C52—H52119.5
C25—C20—C19120.6 (3)C52—C53—C54120.3 (3)
C20—C21—C22120.1 (3)C52—C53—H53119.8
C20—C21—H21119.9C54—C53—H53119.8
C22—C21—H21119.9C55—C54—C53119.9 (3)
C23—C22—C21120.6 (3)C55—C54—H54120.1
C23—C22—H22119.7C53—C54—H54120.1
C21—C22—H22119.7C54—C55—C56120.1 (3)
C24—C23—C22119.5 (3)C54—C55—H55120.0
C24—C23—H23120.3C56—C55—H55120.0
C22—C23—H23120.3C51—C56—C55120.8 (3)
C23—C24—C25120.6 (3)C51—C56—H56119.6
C23—C24—H24119.7C55—C56—H56119.6
C25—C24—H24119.7C58—C57—C62118.2 (3)
C20—C25—C24120.1 (3)C58—C57—C50120.4 (2)
C20—C25—H25119.9C62—C57—C50121.2 (2)
C24—C25—H25119.9C57—C58—C59120.0 (3)
C27—C26—C31118.3 (3)C57—C58—H58120.0
C27—C26—C19122.6 (2)C59—C58—H58120.0
C31—C26—C19119.0 (3)C60—C59—C58120.8 (3)
C26—C27—C28121.1 (3)C60—C59—H59119.6
C26—C27—H27119.5C58—C59—H59119.6
C28—C27—H27119.5C59—C60—C61120.3 (3)
C29—C28—C27119.6 (4)C59—C60—H60119.9
C29—C28—H28120.2C61—C60—H60119.9
C27—C28—H28120.2C60—C61—C62119.7 (3)
C30—C29—C28120.1 (3)C60—C61—H61120.1
C30—C29—H29120.0C62—C61—H61120.1
C28—C29—H29120.0C61—C62—C57121.0 (3)
C29—C30—C31120.7 (3)C61—C62—H62119.5
C29—C30—H30119.7C57—C62—H62119.5
C31—C30—H30119.7C6—O1—C1114.66 (19)
C30—C31—C26120.2 (3)C6—O2—C3113.56 (18)
C30—C31—H31119.9C19—O3—C5113.95 (19)
C26—C31—H31119.9C19—O4—C4114.20 (19)
O6—C32—C33111.3 (2)C37—O5—C34114.3 (2)
O6—C32—H32A109.4C37—O6—C32113.83 (18)
C33—C32—H32A109.4C50—O7—C35114.6 (2)
O6—C32—H32B109.4C36—O8—C50113.54 (19)
O1—C1—C2—C355.4 (3)O6—C37—C38—C3941.2 (3)
O1—C1—C2—C4176.4 (2)C44—C37—C38—C39161.9 (2)
O1—C1—C2—C565.8 (3)C43—C38—C39—C400.8 (4)
C1—C2—C3—O257.3 (3)C37—C38—C39—C40178.7 (3)
C4—C2—C3—O2178.34 (19)C38—C39—C40—C410.0 (5)
C5—C2—C3—O264.4 (3)C39—C40—C41—C421.7 (5)
C1—C2—C4—O465.5 (3)C40—C41—C42—C432.5 (5)
C3—C2—C4—O4176.18 (19)C41—C42—C43—C381.7 (5)
C5—C2—C4—O455.9 (3)C39—C38—C43—C420.0 (4)
C1—C2—C5—O363.5 (3)C37—C38—C43—C42179.5 (3)
C3—C2—C5—O3177.9 (2)O5—C37—C44—C4523.1 (3)
C4—C2—C5—O357.5 (3)O6—C37—C44—C45146.9 (2)
O2—C6—C7—C1232.5 (3)C38—C37—C44—C4595.9 (3)
O1—C6—C7—C12150.7 (2)O5—C37—C44—C49163.8 (2)
C13—C6—C7—C1288.5 (3)O6—C37—C44—C4940.0 (3)
O2—C6—C7—C8147.6 (2)C38—C37—C44—C4977.2 (3)
O1—C6—C7—C829.4 (3)C49—C44—C45—C461.6 (4)
C13—C6—C7—C891.4 (3)C37—C44—C45—C46174.7 (3)
C12—C7—C8—C90.2 (4)C44—C45—C46—C471.7 (5)
C6—C7—C8—C9179.7 (2)C45—C46—C47—C480.7 (5)
C7—C8—C9—C101.0 (4)C46—C47—C48—C490.3 (5)
C8—C9—C10—C111.3 (5)C47—C48—C49—C440.4 (4)
C9—C10—C11—C120.8 (6)C45—C44—C49—C480.5 (4)
C8—C7—C12—C110.4 (5)C37—C44—C49—C48173.8 (2)
C6—C7—C12—C11179.7 (3)O7—C50—C51—C56147.5 (2)
C10—C11—C12—C70.1 (5)O8—C50—C51—C5695.5 (3)
O2—C6—C13—C1834.1 (3)C57—C50—C51—C5625.5 (3)
O1—C6—C13—C18159.0 (2)O7—C50—C51—C5235.5 (3)
C7—C6—C13—C1884.0 (3)O8—C50—C51—C5281.5 (3)
O2—C6—C13—C14153.1 (2)C57—C50—C51—C52157.6 (2)
O1—C6—C13—C1428.2 (3)C56—C51—C52—C530.1 (4)
C7—C6—C13—C1488.8 (3)C50—C51—C52—C53177.0 (2)
C18—C13—C14—C150.7 (4)C51—C52—C53—C540.5 (5)
C6—C13—C14—C15173.7 (3)C52—C53—C54—C551.2 (5)
C13—C14—C15—C160.4 (5)C53—C54—C55—C561.4 (5)
C14—C15—C16—C170.5 (5)C52—C51—C56—C550.4 (4)
C15—C16—C17—C181.1 (5)C50—C51—C56—C55176.6 (3)
C16—C17—C18—C130.7 (5)C54—C55—C56—C511.1 (5)
C14—C13—C18—C170.2 (4)O7—C50—C57—C5832.1 (3)
C6—C13—C18—C17173.2 (3)O8—C50—C57—C58156.1 (2)
O3—C19—C20—C2116.2 (3)C51—C50—C57—C5887.0 (3)
O4—C19—C20—C21102.1 (3)O7—C50—C57—C62152.1 (2)
C26—C19—C20—C21137.6 (2)O8—C50—C57—C6228.1 (3)
O3—C19—C20—C25165.6 (2)C51—C50—C57—C6288.7 (3)
O4—C19—C20—C2576.1 (3)C62—C57—C58—C590.4 (4)
C26—C19—C20—C2544.2 (3)C50—C57—C58—C59176.2 (3)
C25—C20—C21—C220.3 (4)C57—C58—C59—C600.4 (5)
C19—C20—C21—C22178.6 (2)C58—C59—C60—C611.8 (5)
C20—C21—C22—C230.3 (4)C59—C60—C61—C622.5 (5)
C21—C22—C23—C240.1 (5)C60—C61—C62—C571.8 (4)
C22—C23—C24—C250.4 (5)C58—C57—C62—C610.3 (4)
C21—C20—C25—C240.0 (4)C50—C57—C62—C61175.5 (3)
C19—C20—C25—C24178.3 (3)O2—C6—O1—C152.8 (3)
C23—C24—C25—C200.3 (5)C7—C6—O1—C1168.03 (19)
O3—C19—C26—C27144.8 (2)C13—C6—O1—C172.3 (3)
O4—C19—C26—C2720.6 (3)C2—C1—O1—C655.2 (3)
C20—C19—C26—C2796.1 (3)O1—C6—O2—C354.6 (3)
O3—C19—C26—C3139.5 (3)C7—C6—O2—C3169.05 (19)
O4—C19—C26—C31163.6 (2)C13—C6—O2—C370.8 (2)
C20—C19—C26—C3179.6 (3)C2—C3—O2—C658.7 (2)
C31—C26—C27—C280.2 (4)O4—C19—O3—C554.4 (3)
C19—C26—C27—C28175.5 (3)C20—C19—O3—C5168.66 (19)
C26—C27—C28—C290.6 (5)C26—C19—O3—C569.8 (2)
C27—C28—C29—C301.0 (5)C2—C5—O3—C1959.0 (3)
C28—C29—C30—C311.1 (5)O3—C19—O4—C452.7 (3)
C29—C30—C31—C260.8 (5)C20—C19—O4—C4168.2 (2)
C27—C26—C31—C300.3 (4)C26—C19—O4—C471.4 (3)
C19—C26—C31—C30175.6 (3)C2—C4—O4—C1955.7 (3)
O6—C32—C33—C36174.8 (2)O6—C37—O5—C3455.3 (3)
O6—C32—C33—C3454.1 (3)C38—C37—O5—C34168.41 (19)
O6—C32—C33—C3567.2 (3)C44—C37—O5—C3468.9 (3)
C36—C33—C34—O5174.3 (2)C33—C34—O5—C3756.6 (3)
C32—C33—C34—O553.6 (3)O5—C37—O6—C3255.4 (3)
C35—C33—C34—O567.7 (3)C38—C37—O6—C32168.99 (19)
C36—C33—C35—O754.7 (3)C44—C37—O6—C3269.6 (2)
C32—C33—C35—O7175.2 (2)C33—C32—O6—C3757.2 (3)
C34—C33—C35—O765.9 (3)O8—C50—O7—C3554.0 (3)
C32—C33—C36—O8176.61 (19)C57—C50—O7—C3570.3 (3)
C34—C33—C36—O865.0 (3)C51—C50—O7—C35166.62 (19)
C35—C33—C36—O855.7 (3)C33—C35—O7—C5056.3 (3)
O5—C37—C38—C43105.2 (3)C33—C36—O8—C5057.6 (3)
O6—C37—C38—C43138.3 (2)O7—C50—O8—C3654.4 (3)
C44—C37—C38—C4317.6 (3)C57—C50—O8—C3669.9 (3)
O5—C37—C38—C3975.3 (3)C51—C50—O8—C36168.1 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C9—H9···Cg1i0.932.833.722 (2)161
C30—H30···Cg2ii0.932.843.523 (3)131
C3—H3A···O6ii0.972.533.436 (3)156
Symmetry codes: (i) x+1, y, z+1; (ii) x+1, y+1, z+1.

Experimental details

Crystal data
Chemical formulaC31H28O4
Mr464.53
Crystal system, space groupTriclinic, P1
Temperature (K)295
a, b, c (Å)13.509 (3), 13.790 (3), 15.626 (5)
α, β, γ (°)102.327 (7), 104.199 (6), 112.170 (4)
V3)2456.8 (11)
Z4
Radiation typeMo Kα
µ (mm1)0.08
Crystal size (mm)0.26 × 0.22 × 0.20
Data collection
DiffractometerBruker APEXII CCD
Absorption correctionMulti-scan
(SADABS; Bruker, 2000)
Tmin, Tmax0.979, 0.984
No. of measured, independent and
observed [I > 2σ(I)] reflections
13730, 8545, 5355
Rint0.026
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.053, 0.196, 1.01
No. of reflections8545
No. of parameters631
No. of restraints1
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.23, 0.28

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C9—H9···Cg1i0.932.833.722 (2)161
C30—H30···Cg2ii0.932.843.523 (3)131
C3—H3A···O6ii0.972.533.436 (3)156
Symmetry codes: (i) x+1, y, z+1; (ii) x+1, y+1, z+1.
 

Acknowledgements

The authors gratefully acknowledge financial support from the Natural Science Foundation of China (grant No. 20872051).

References

First citationBruker (2000). SAINT, SMART and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationCismaş, C., Terec, A., Mager, S. & Grosu, I. (2005). Curr. Org. Chem. 9, 1287–1314.  Google Scholar
First citationMihiş, A., Condamine, E., Bogdan, E., Terec, A., Kurtán, T. & Grosu, I. (2008). Molecules, 13, 2848–2858.  Web of Science PubMed Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSun, X., Yu, S.-L., Li, Z.-Y. & Yang, Y. (2010). J. Mol. Struct. 973, 152–156.  Web of Science CSD CrossRef CAS Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds