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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

Tri­cyclo­[6.2.1.02,7]undeca-4,9-diene-3,6-dione

aSchool of Environment and Energy Engineering, Beijing University of Civil Engineering and Architecture, 100044 Beijing, People's Republic of China
*Correspondence e-mail: chongchenwang@126.com

(Received 8 September 2008; accepted 19 September 2008; online 24 September 2008)

The title compound, C11H10O2, crystallizes with two independent mol­ecules in the asymmetric unit. In one mol­ecule, the dihedral angle between the mean planes of the C—C=C—C group of the diene unit and essentially planar cyclo­hexene ring is 51.07 (9)°, while in the other mol­ecule it is 54.49 (12)°. In the crystal structure, weak inter­molecular C—H⋯O inter­actions link the mol­ecules into columns along the b axis.

Related literature

For background information, see: Ito et al. (2007[Ito, F. M., Petroni, J. M., de Lima, D. P., Beatriz, A., Marques, M. R., de Moraes, M. O., Costa-Lotufo, L. V., Montenegro, R. C., Magalhães, H. I. F., do, Ó. & Pessoa, C. (2007). Molecules, 12, 271-282.]); Mgani et al. (1995[Mgani, Q. A., Nkunya, M., Zwanenburg, B. & Klunder, A. (1995). Tetrahedron Lett. 26, 4661-4664.]).

[Scheme 1]

Experimental

Crystal data
  • C11H10O2

  • Mr = 174.19

  • Monoclinic, P 21 /c

  • a = 15.649 (3) Å

  • b = 6.5399 (13) Å

  • c = 21.448 (7) Å

  • β = 125.05 (2)°

  • V = 1797.0 (8) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 0.09 mm−1

  • T = 293 (2) K

  • 0.52 × 0.12 × 0.11 mm

Data collection
  • Rigaku R-AXIS RAPID IP area-detector diffractometer

  • Absorption correction: multi-scan (ABSCOR; Higashi, 1995[Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.956, Tmax = 0.990

  • 6936 measured reflections

  • 4119 independent reflections

  • 2664 reflections with I > 2σ(I)

  • Rint = 0.036

Refinement
  • R[F2 > 2σ(F2)] = 0.066

  • wR(F2) = 0.210

  • S = 1.03

  • 4119 reflections

  • 251 parameters

  • H-atom parameters constrained

  • Δρmax = 0.22 e Å−3

  • Δρmin = −0.21 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C2—H2A⋯O4i 0.93 2.58 3.502 (3) 172
C6—H6A⋯O2ii 0.98 2.53 3.446 (3) 155
C11—H11A⋯O3iii 0.93 2.58 3.335 (4) 138
C16—H16A⋯O1i 0.98 2.59 3.416 (3) 142
C17—H17A⋯O4iv 0.98 2.51 3.319 (3) 140
Symmetry codes: (i) -x+1, -y, -z; (ii) x, y+1, z; (iii) [x, -y-{\script{1\over 2}}, z+{\script{1\over 2}}]; (iv) x, y-1, z.

Data collection: RAPID-AUTO (Rigaku, 2001[Rigaku (2001). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan.]); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]) and PLATON (Spek, 2003[Spek, A. L. (2003). J. Appl. Cryst. 36, 7-13.]); software used to prepare material for publication: SHELXTL.

Supporting information


Comment top

The title compound, tricyclo[6.2.1.02,7]undeca-4,9-diene-3,6 -dione formed by the cycloaddition between cyclopentadiene and p-benzoquinone has been investigated widely ( Ito et al. 2007; Mgani, et al. 1995). One of the unique aspect of the title compound is its high molecular symmetry, which allows for facile selective reactions at one or both carbonyl groups by means of classical and non-classical reagents. Another feature to be considered is its cage-like framework, which forces functional groups into close spatial proximity, facilitating subsequent reactions (Ito et al. 2007).

The title compound crystallizes with two independent molecules in the asymmetric unit, as shown in Fig.1. In one molecule, the dihedral angle between the mean planes of C-C=C-C group of the diene unit and essentially planar cyclohexene ring is [C1-C6] 51.07 (9)° while in the other [C12-C17] it is 54.49 (12)°. In the crystal structure, weak intermolecular C—H···O interactions link the molecules into columns along the b-axis (Fig .2).

Related literature top

For background information, see: Ito et al. (2007); Mgani et al. (1995).

Experimental top

Tricyclo[6.2.1.02,7]undeca-4,9-diene-3,6-dione was obtained by the method described in the literature (Ito et al. 2007). The crystals of the title compound was recrystallized from hexane under low temperature (273.15 K).

Refinement top

All H atoms were fixed geometrically, with C—H distances of 0.93–98 Å with a mixture of treatments for the isotropic displacement parameters. In most case the isotropic displacement parameters were refined but in a few cases the value of Uiso(H) = 1.2Ueq(C).

Computing details top

Data collection: RAPID-AUTO (Rigaku, 2001); cell refinement: RAPID-AUTO (Rigaku, 2001); data reduction: RAPID-AUTO (Rigaku, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2003); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The asymmetric unit of the title compound, showing atoms labelling. Displacement ellipoids are drawn at the 50% probability level.
[Figure 2] Fig. 2. Packing diagram.
Tricyclo[6.2.1.02,7]undeca-4,9-diene-3,6-dione top
Crystal data top
C11H10O2F(000) = 736
Mr = 174.19Dx = 1.288 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 16732 reflections
a = 15.649 (3) Åθ = 1.6–27.5°
b = 6.5399 (13) ŵ = 0.09 mm1
c = 21.448 (7) ÅT = 293 K
β = 125.05 (2)°Needle, dark brown
V = 1797.0 (8) Å30.52 × 0.12 × 0.11 mm
Z = 8
Data collection top
Rigaku R-AXIS RAPID IP area-detector
diffractometer
4119 independent reflections
Radiation source: Rotating Anode2664 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.036
ω oscillation scansθmax = 27.5°, θmin = 1.6°
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)
h = 2020
Tmin = 0.956, Tmax = 0.990k = 88
6936 measured reflectionsl = 2727
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)] = 0.066Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.210H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.118P)2 + 0.1983P]
where P = (Fo2 + 2Fc2)/3
4119 reflections(Δ/σ)max < 0.001
251 parametersΔρmax = 0.22 e Å3
0 restraintsΔρmin = 0.21 e Å3
Crystal data top
C11H10O2V = 1797.0 (8) Å3
Mr = 174.19Z = 8
Monoclinic, P21/cMo Kα radiation
a = 15.649 (3) ŵ = 0.09 mm1
b = 6.5399 (13) ÅT = 293 K
c = 21.448 (7) Å0.52 × 0.12 × 0.11 mm
β = 125.05 (2)°
Data collection top
Rigaku R-AXIS RAPID IP area-detector
diffractometer
4119 independent reflections
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)
2664 reflections with I > 2σ(I)
Tmin = 0.956, Tmax = 0.990Rint = 0.036
6936 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0660 restraints
wR(F2) = 0.210H-atom parameters constrained
S = 1.03Δρmax = 0.22 e Å3
4119 reflectionsΔρmin = 0.21 e Å3
251 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
O10.29192 (15)0.0348 (3)0.02418 (12)0.0946 (7)
O20.1016 (2)0.5875 (3)0.16845 (10)0.1029 (8)
C10.23966 (16)0.1048 (3)0.01874 (12)0.0551 (5)
C20.28081 (17)0.3137 (4)0.00061 (13)0.0596 (6)
H2A0.34250.33970.04670.074 (7)*
C30.23343 (19)0.4665 (4)0.04914 (13)0.0616 (6)
H3A0.26310.59600.03420.080 (8)*
C40.13635 (19)0.4419 (4)0.12469 (12)0.0581 (6)
C50.07944 (16)0.2423 (3)0.14694 (10)0.0490 (5)
H5A0.06550.19900.19570.067 (7)*
C60.13399 (15)0.0649 (3)0.08969 (11)0.0478 (5)
H6A0.13910.05140.11620.066 (7)*
C70.05338 (18)0.0092 (4)0.07124 (13)0.0638 (7)
H7A0.06330.12360.04680.082 (8)*
C80.04733 (19)0.0353 (5)0.15063 (15)0.0781 (8)
H8A0.10950.01480.15160.111 (11)*
H8B0.04970.04980.18860.082 (8)*
C90.02716 (19)0.2589 (5)0.15655 (14)0.0706 (7)
H9A0.08280.33110.20220.096 (9)*
C100.0019 (2)0.3395 (5)0.08217 (17)0.0799 (8)
H10A0.01750.46910.07350.096*
C110.0467 (2)0.1914 (5)0.03133 (15)0.0760 (8)
H11A0.07210.19860.01990.091*
O30.2497 (2)0.2686 (4)0.34967 (12)0.1181 (10)
O40.48892 (15)0.3614 (3)0.18269 (12)0.0870 (6)
C120.3043 (2)0.1294 (4)0.30817 (13)0.0652 (6)
C130.28648 (19)0.0779 (4)0.33792 (13)0.0656 (6)
H13A0.23230.10120.38860.092 (9)*
C140.34485 (18)0.2354 (4)0.29597 (14)0.0620 (6)
H14A0.32890.36450.31820.082 (9)*
C150.43306 (16)0.2141 (3)0.21624 (13)0.0541 (5)
C160.45436 (15)0.0118 (3)0.17730 (11)0.0504 (5)
H16A0.52780.02210.15400.050 (6)*
C170.38776 (16)0.1714 (3)0.22614 (11)0.0511 (5)
H17A0.43480.27530.22360.066 (7)*
C180.34259 (19)0.2549 (4)0.18255 (14)0.0665 (7)
H18A0.31640.39560.19480.070 (7)*
C190.4353 (2)0.2168 (5)0.10083 (14)0.0796 (8)
H19A0.49840.28470.08860.083 (9)*
H19B0.42120.25080.06360.129 (13)*
C200.4363 (2)0.0123 (5)0.11275 (13)0.0755 (8)
H20A0.48630.09230.06730.085 (8)*
C210.3220 (3)0.0601 (6)0.15010 (19)0.0928 (10)
H21A0.29520.18070.14490.111*
C220.2675 (2)0.0992 (5)0.19120 (19)0.0837 (9)
H22A0.19530.11200.22030.100*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0699 (12)0.0600 (11)0.0883 (13)0.0093 (9)0.0071 (10)0.0161 (10)
O20.152 (2)0.0603 (12)0.0557 (11)0.0017 (12)0.0360 (12)0.0137 (9)
C10.0451 (11)0.0487 (12)0.0563 (12)0.0051 (9)0.0203 (10)0.0048 (10)
C20.0436 (11)0.0587 (14)0.0559 (12)0.0071 (10)0.0165 (10)0.0076 (11)
C30.0689 (14)0.0461 (13)0.0621 (13)0.0107 (10)0.0332 (12)0.0048 (10)
C40.0789 (15)0.0498 (13)0.0433 (10)0.0029 (10)0.0337 (11)0.0023 (9)
C50.0531 (11)0.0533 (12)0.0338 (9)0.0004 (9)0.0210 (8)0.0037 (8)
C60.0473 (11)0.0420 (11)0.0495 (10)0.0025 (8)0.0252 (9)0.0044 (9)
C70.0566 (13)0.0709 (16)0.0573 (12)0.0184 (11)0.0290 (11)0.0016 (11)
C80.0511 (14)0.107 (2)0.0661 (15)0.0232 (14)0.0278 (12)0.0209 (15)
C90.0462 (12)0.091 (2)0.0531 (12)0.0129 (12)0.0158 (10)0.0009 (13)
C100.0608 (15)0.099 (2)0.0882 (19)0.0061 (14)0.0478 (15)0.0189 (17)
C110.0644 (15)0.116 (2)0.0589 (14)0.0220 (15)0.0421 (13)0.0195 (15)
O30.140 (2)0.0854 (15)0.0597 (11)0.0461 (14)0.0168 (12)0.0131 (10)
O40.0699 (11)0.0565 (11)0.0983 (14)0.0123 (9)0.0271 (10)0.0112 (10)
C120.0673 (14)0.0638 (16)0.0458 (11)0.0136 (11)0.0216 (11)0.0050 (10)
C130.0593 (13)0.0700 (16)0.0463 (12)0.0002 (11)0.0179 (10)0.0078 (11)
C140.0592 (13)0.0550 (14)0.0658 (13)0.0049 (10)0.0323 (12)0.0107 (11)
C150.0439 (11)0.0511 (13)0.0637 (13)0.0030 (9)0.0288 (10)0.0090 (10)
C160.0380 (10)0.0581 (13)0.0476 (10)0.0017 (8)0.0201 (9)0.0036 (9)
C170.0529 (11)0.0498 (12)0.0485 (11)0.0011 (9)0.0279 (9)0.0009 (9)
C180.0641 (14)0.0672 (16)0.0671 (14)0.0060 (12)0.0370 (12)0.0097 (12)
C190.0854 (19)0.099 (2)0.0553 (14)0.0059 (16)0.0409 (14)0.0162 (14)
C200.0889 (19)0.089 (2)0.0512 (13)0.0114 (15)0.0418 (13)0.0153 (13)
C210.123 (3)0.095 (2)0.113 (2)0.024 (2)0.098 (2)0.005 (2)
C220.0706 (17)0.098 (2)0.104 (2)0.0038 (16)0.0628 (17)0.0162 (19)
Geometric parameters (Å, º) top
O1—C11.219 (3)O3—C121.215 (3)
O2—C41.224 (3)O4—C151.220 (3)
C1—C21.464 (3)C12—C131.456 (4)
C1—C61.493 (3)C12—C171.496 (3)
C2—C31.321 (3)C13—C141.327 (3)
C2—H2A0.9301C13—H13A0.9300
C3—C41.460 (3)C14—C151.462 (3)
C3—H3A0.9299C14—H14A0.9300
C4—C51.495 (3)C15—C161.497 (3)
C5—C61.542 (3)C16—C171.538 (3)
C5—C91.563 (3)C16—C201.564 (3)
C5—H5A0.9799C16—H16A0.9800
C6—C71.567 (3)C17—C181.559 (3)
C6—H6A0.9800C17—H17A0.9800
C7—C111.505 (4)C18—C221.483 (4)
C7—C81.526 (3)C18—C191.523 (4)
C7—H7A0.9800C18—H18A0.9800
C8—C91.517 (4)C19—C201.522 (4)
C8—H8A0.9702C19—H19A0.9700
C8—H8B0.9700C19—H19B0.9700
C9—C101.502 (4)C20—C211.514 (4)
C9—H9A0.9801C20—H20A0.9801
C10—C111.324 (4)C21—C221.314 (4)
C10—H10A0.9300C21—H21A0.9300
C11—H11A0.9300C22—H22A0.9300
O1—C1—C2119.8 (2)O3—C12—C13120.0 (2)
O1—C1—C6120.6 (2)O3—C12—C17119.7 (2)
C2—C1—C6119.63 (18)C13—C12—C17120.3 (2)
C3—C2—C1122.3 (2)C14—C13—C12122.8 (2)
C3—C2—H2A118.8C14—C13—H13A118.4
C1—C2—H2A118.9C12—C13—H13A118.8
C2—C3—C4123.1 (2)C13—C14—C15122.6 (2)
C2—C3—H3A118.3C13—C14—H14A118.7
C4—C3—H3A118.6C15—C14—H14A118.7
O2—C4—C3119.1 (2)O4—C15—C14119.4 (2)
O2—C4—C5120.9 (2)O4—C15—C16121.0 (2)
C3—C4—C5120.00 (19)C14—C15—C16119.67 (19)
C4—C5—C6116.52 (17)C15—C16—C17117.52 (17)
C4—C5—C9112.11 (19)C15—C16—C20113.36 (19)
C6—C5—C9102.60 (18)C17—C16—C20102.03 (18)
C4—C5—H5A108.6C15—C16—H16A107.7
C6—C5—H5A108.3C17—C16—H16A108.0
C9—C5—H5A108.3C20—C16—H16A107.8
C1—C6—C5117.58 (17)C12—C17—C16116.78 (19)
C1—C6—C7111.38 (18)C12—C17—C18112.29 (19)
C5—C6—C7102.61 (17)C16—C17—C18103.15 (17)
C1—C6—H6A108.4C12—C17—H17A108.2
C5—C6—H6A108.3C16—C17—H17A108.0
C7—C6—H6A108.1C18—C17—H17A108.0
C11—C7—C8100.5 (2)C22—C18—C19101.2 (2)
C11—C7—C6106.78 (19)C22—C18—C17106.5 (2)
C8—C7—C699.07 (18)C19—C18—C1799.93 (19)
C11—C7—H7A116.0C22—C18—H18A115.5
C8—C7—H7A116.2C19—C18—H18A115.9
C6—C7—H7A116.0C17—C18—H18A115.6
C9—C8—C794.01 (19)C20—C19—C1893.6 (2)
C9—C8—H8A112.7C20—C19—H19A112.9
C7—C8—H8A112.9C18—C19—H19A112.7
C9—C8—H8B113.1C20—C19—H19B113.1
C7—C8—H8B112.9C18—C19—H19B113.2
H8A—C8—H8B110.4H19A—C19—H19B110.5
C10—C9—C8100.9 (2)C21—C20—C1999.8 (3)
C10—C9—C5105.94 (19)C21—C20—C16106.9 (2)
C8—C9—C5100.4 (2)C19—C20—C1699.8 (2)
C10—C9—H9A115.7C21—C20—H20A116.2
C8—C9—H9A116.1C19—C20—H20A116.0
C5—C9—H9A115.7C16—C20—H20A115.8
C11—C10—C9107.1 (3)C22—C21—C20107.8 (3)
C11—C10—H10A126.4C22—C21—H21A126.1
C9—C10—H10A126.4C20—C21—H21A126.1
C10—C11—C7107.8 (2)C21—C22—C18107.4 (3)
C10—C11—H11A126.1C21—C22—H22A126.3
C7—C11—H11A126.1C18—C22—H22A126.3
O1—C1—C2—C3171.7 (3)O3—C12—C13—C14178.5 (3)
C6—C1—C2—C38.3 (4)C17—C12—C13—C143.1 (4)
C1—C2—C3—C40.1 (4)C12—C13—C14—C150.7 (4)
C2—C3—C4—O2174.5 (3)C13—C14—C15—O4173.9 (3)
C2—C3—C4—C57.1 (4)C13—C14—C15—C165.3 (4)
O2—C4—C5—C6175.9 (2)O4—C15—C16—C17173.3 (2)
C3—C4—C5—C65.7 (3)C14—C15—C16—C175.9 (3)
O2—C4—C5—C966.3 (3)O4—C15—C16—C2068.0 (3)
C3—C4—C5—C9112.1 (2)C14—C15—C16—C20112.8 (2)
O1—C1—C6—C5171.2 (2)O3—C12—C17—C16179.5 (3)
C2—C1—C6—C58.9 (3)C13—C12—C17—C162.1 (3)
O1—C1—C6—C770.9 (3)O3—C12—C17—C1861.7 (3)
C2—C1—C6—C7109.1 (2)C13—C12—C17—C18116.7 (3)
C4—C5—C6—C12.1 (3)C15—C16—C17—C122.3 (3)
C9—C5—C6—C1124.9 (2)C20—C16—C17—C12122.3 (2)
C4—C5—C6—C7120.51 (19)C15—C16—C17—C18125.9 (2)
C9—C5—C6—C72.3 (2)C20—C16—C17—C181.3 (2)
C1—C6—C7—C1161.5 (2)C12—C17—C18—C2257.7 (3)
C5—C6—C7—C1165.1 (2)C16—C17—C18—C2268.9 (2)
C1—C6—C7—C8165.4 (2)C12—C17—C18—C19162.6 (2)
C5—C6—C7—C838.8 (2)C16—C17—C18—C1936.0 (2)
C11—C7—C8—C949.1 (2)C22—C18—C19—C2050.3 (2)
C6—C7—C8—C960.0 (2)C17—C18—C19—C2058.9 (2)
C7—C8—C9—C1049.8 (2)C18—C19—C20—C2149.3 (2)
C7—C8—C9—C558.9 (2)C18—C19—C20—C1659.9 (2)
C4—C5—C9—C1056.3 (3)C15—C16—C20—C2162.2 (3)
C6—C5—C9—C1069.4 (3)C17—C16—C20—C2165.2 (3)
C4—C5—C9—C8160.98 (18)C15—C16—C20—C19165.6 (2)
C6—C5—C9—C835.2 (2)C17—C16—C20—C1938.3 (2)
C8—C9—C10—C1133.6 (3)C19—C20—C21—C2233.2 (3)
C5—C9—C10—C1170.6 (3)C16—C20—C21—C2270.3 (3)
C9—C10—C11—C70.7 (3)C20—C21—C22—C180.0 (3)
C8—C7—C11—C1032.2 (3)C19—C18—C22—C2133.3 (3)
C6—C7—C11—C1070.7 (3)C17—C18—C22—C2170.7 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C2—H2A···O4i0.932.583.502 (3)172
C6—H6A···O2ii0.982.533.446 (3)155
C11—H11A···O3iii0.932.583.335 (4)138
C16—H16A···O1i0.982.593.416 (3)142
C17—H17A···O4iv0.982.513.319 (3)140
Symmetry codes: (i) x+1, y, z; (ii) x, y+1, z; (iii) x, y1/2, z+1/2; (iv) x, y1, z.

Experimental details

Crystal data
Chemical formulaC11H10O2
Mr174.19
Crystal system, space groupMonoclinic, P21/c
Temperature (K)293
a, b, c (Å)15.649 (3), 6.5399 (13), 21.448 (7)
β (°) 125.05 (2)
V3)1797.0 (8)
Z8
Radiation typeMo Kα
µ (mm1)0.09
Crystal size (mm)0.52 × 0.12 × 0.11
Data collection
DiffractometerRigaku R-AXIS RAPID IP area-detector
diffractometer
Absorption correctionMulti-scan
(ABSCOR; Higashi, 1995)
Tmin, Tmax0.956, 0.990
No. of measured, independent and
observed [I > 2σ(I)] reflections
6936, 4119, 2664
Rint0.036
(sin θ/λ)max1)0.649
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.066, 0.210, 1.03
No. of reflections4119
No. of parameters251
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.22, 0.21

Computer programs: RAPID-AUTO (Rigaku, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2003), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C2—H2A···O4i0.932.583.502 (3)172
C6—H6A···O2ii0.982.533.446 (3)155
C11—H11A···O3iii0.932.583.335 (4)138
C16—H16A···O1i0.982.593.416 (3)142
C17—H17A···O4iv0.982.513.319 (3)140
Symmetry codes: (i) x+1, y, z; (ii) x, y+1, z; (iii) x, y1/2, z+1/2; (iv) x, y1, z.
 

Acknowledgements

The author gratefully acknowledges financial support by the Beijing Academic Innovation Group in Sustainable Water/Waste Recycling Technologies (grant No. BJE10016200611), the Research Fund of Beijing University of Civil Engineering and Architecture (grant No. 100700502) and the Funding Project for Academic Human Resources Development in Institutions of Higher Learning Under the Jurisdiction of Beijing Municipality (grant No. BJE10016200611).

References

First citationHigashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.  Google Scholar
First citationIto, F. M., Petroni, J. M., de Lima, D. P., Beatriz, A., Marques, M. R., de Moraes, M. O., Costa-Lotufo, L. V., Montenegro, R. C., Magalhães, H. I. F., do, Ó. & Pessoa, C. (2007). Molecules, 12, 271–282.  Web of Science CrossRef PubMed CAS Google Scholar
First citationMgani, Q. A., Nkunya, M., Zwanenburg, B. & Klunder, A. (1995). Tetrahedron Lett. 26, 4661–4664.  CrossRef Web of Science Google Scholar
First citationRigaku (2001). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSpek, A. L. (2003). J. Appl. Cryst. 36, 7–13.  Web of Science CrossRef CAS IUCr Journals 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