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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

(E)-2,2′-[3-(2-Nitro­phen­yl)prop-2-ene-1,1-di­yl]bis­­(3-hy­dr­oxy-5,5-di­methyl­cyclo­hex-2-en-1-one)

aAdvanced Analysis Center, Korea Institute of Science and Technology, Hwarangro 14-gil, Seongbuk-gu, Seoul 136-791, Republic of Korea, and bCenter for Neuro-Medicine, Korea Institute of Science and Technology, Hwarangro 14-gil, Seongbuk-gu, Seoul 136-791, Republic of Korea
*Correspondence e-mail: j9601@kist.re.kr

(Received 8 October 2011; accepted 21 October 2011; online 2 November 2011)

In the title compound, C25H29NO6, each of the cyclo­hexenone rings adopts a half-chair conformation. Each of the pairs of hy­droxy and carbonyl O atoms are oriented to allow for the formation of intra­molecular O—H⋯O hydrogen bonds, which are typical of xanthene derivatives. The nitro group is rotationally disordered over two orientations in a 0.544 (6):0.456 (6) ratio. In the crystal, weak inter­molecualr C—H⋯O hydrogen bonds link mol­ecules into layers parallel to the ab plane.

Related literature

For related structures of xanthenes, see: Bolte et al. (2001[Bolte, M., Degen, A. & Rühl, S. (2001). Acta Cryst. C57, 446-451.]); Palakshi Reddy et al. (2010[Palakshi Reddy, B., Vijayakumar, V., Sarveswari, S., Ng, S. W. & Tiekink, E. R. T. (2010). Acta Cryst. E66, o2806-o2807.]); Zhu et al. (2011[Zhu, Y.-L., Xiao, G.-L., Chen, Y.-F., Chen, R.-T. & Zhou, Y. (2011). Acta Cryst. E67, o2398.]); Cha et al. (2011[Cha, J. H., Son, M. H., Min, S.-J., Cho, Y. S. & Lee, J. K. (2011). Acta Cryst. E67, o2739.]).

[Scheme 1]

Experimental

Crystal data
  • C25H29NO6

  • Mr = 439.51

  • Triclinic, [P \overline 1]

  • a = 9.8306 (14) Å

  • b = 11.0841 (14) Å

  • c = 11.9602 (13) Å

  • α = 69.601 (3)°

  • β = 79.867 (4)°

  • γ = 72.588 (4)°

  • V = 1161.8 (3) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.09 mm−1

  • T = 298 K

  • 0.20 × 0.10 × 0.10 mm

Data collection
  • Rigaku R-AXIS RAPID diffractometer

  • Absorption correction: multi-scan (ABSCOR; Rigaku, 1995[Rigaku (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.657, Tmax = 0.991

  • 9400 measured reflections

  • 4194 independent reflections

  • 1687 reflections with F2 > 2σ(F2)

  • Rint = 0.062

Refinement
  • R[F2 > 2σ(F2)] = 0.064

  • wR(F2) = 0.191

  • S = 0.99

  • 4194 reflections

  • 313 parameters

  • 336 restraints

  • H-atom parameters constrained

  • Δρmax = 0.38 e Å−3

  • Δρmin = −0.45 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O2—H2⋯O4 0.82 1.82 2.617 (4) 165
O3—H3A⋯O1 0.82 1.83 2.611 (4) 158
C16—H16C⋯O6i 0.96 2.56 3.449 (11) 155
C20—H20A⋯O5ii 0.97 2.58 3.509 (12) 161
C22—H22A⋯O4iii 0.97 2.58 3.530 (5) 165
C22—H22B⋯O6aii 0.97 2.54 3.342 (9) 140
Symmetry codes: (i) -x+1, -y+2, -z+1; (ii) x-1, y, z; (iii) -x+1, -y+1, -z+1.

Data collection: RAPID-AUTO (Rigaku, 2006[Rigaku (2006). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan.]); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; program(s) used to solve structure: IL MILIONE (Burla et al., 2007[Burla, M. C., Caliandro, R., Camalli, M., Carrozzini, B., Cascarano, G. L., De Caro, L., Giacovazzo, C., Polidori, G., Siliqi, D. & Spagna, R. (2007). J. Appl. Cryst. 40, 609-613.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: CrystalStructure (Rigaku, 2010[Rigaku (2010). CrystalStructure. Rigaku Corporation, Tokyo, Japan.]); software used to prepare material for publication: CrystalStructure.

Supporting information


Comment top

As a part of our ongoing study of the substituent effect on the solid state structures of Xanthene derivatives (Cha et al., 2011) we present here the crystal structure of the title compound (I) (Fig. 1).

In (I) (Fig. 1), the bond lengths and angles are normal and correspond to those observed in related structures (Bolte et al., 2001; Palakshi Reddy et al., 2010; Zhu et al., 2011; Cha et al., 2011). In the title compound, the dihedral angle between the 2-nitrobenzene and 3-hydroxy-5,5-dimethylcyclohex-2-enone rings are 69.6 (4)° and 42.1 (1)°, respectively. All two cyclohexenone rings in (Fig.1) display half-chair conformation. The hydroxy and carbonyl O atoms face each other and are orientated to allow for the formation of two intramolecular O—H···O hydrogen bonds (Table 1) which are typical of xanthene derivatives. The nitro group is rotationally disordered over two orientations in a ratio 0.544 (6):0.456 (6).

In the crystal, weak intermolecular C—H···O hydrogen bonds (Table 1) link molecules into layers parallel to the ab plane.

Related literature top

For related structures of xanthenes, see: Bolte et al. (2001); Palakshi Reddy et al. (2010); Zhu et al. (2011); Cha et al. (2011).

Experimental top

To solution of 1,3-cyclohexanedione (4.61 mmol), 2-nitrocinnamaldehyde (1.84 mmol) and 4° MS was added catalytic amounts of L-proline (0.47 mmol) in under nitrogen atmosphere. After stirring for 5 h, The anhydrous ethyl acetate (0.5 ml) was added to a reaction mixture and the solution was stirred for 3 days. The reaction mixture was filtered through pad of celite to remove MS and concentrated. The residue oil was purified by flash column chromatography to afford product which was recrystallized from ethanol to give crystals suitable for X-ray analysis.

Refinement top

All H atoms were positioned geometrically and refined using a riding model with C—H = 0.93–0.98 Å and Uiso(H) = 1.2 or 1.5Ueq(C). Rotating group model was applied for the methyl groups. The nitro group was refined as disordered over two orientations.

Structure description top

As a part of our ongoing study of the substituent effect on the solid state structures of Xanthene derivatives (Cha et al., 2011) we present here the crystal structure of the title compound (I) (Fig. 1).

In (I) (Fig. 1), the bond lengths and angles are normal and correspond to those observed in related structures (Bolte et al., 2001; Palakshi Reddy et al., 2010; Zhu et al., 2011; Cha et al., 2011). In the title compound, the dihedral angle between the 2-nitrobenzene and 3-hydroxy-5,5-dimethylcyclohex-2-enone rings are 69.6 (4)° and 42.1 (1)°, respectively. All two cyclohexenone rings in (Fig.1) display half-chair conformation. The hydroxy and carbonyl O atoms face each other and are orientated to allow for the formation of two intramolecular O—H···O hydrogen bonds (Table 1) which are typical of xanthene derivatives. The nitro group is rotationally disordered over two orientations in a ratio 0.544 (6):0.456 (6).

In the crystal, weak intermolecular C—H···O hydrogen bonds (Table 1) link molecules into layers parallel to the ab plane.

For related structures of xanthenes, see: Bolte et al. (2001); Palakshi Reddy et al. (2010); Zhu et al. (2011); Cha et al. (2011).

Computing details top

Data collection: RAPID AUTO (Rigaku, 2006); cell refinement: RAPID AUTO (Rigaku, 2006); data reduction: RAPID AUTO (Rigaku, 2006); program(s) used to solve structure: IL MILIONE (Burla et al., 2007); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: CrystalStructure (Rigaku, 2010); software used to prepare material for publication: CrystalStructure (Rigaku, 2010).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I) showing the atomic numbering and 50% probability displacement ellipsoid. Only major part of the disordered nitro group is shown.
(E)-2,2'-[3-(2-Nitrophenyl)prop-2-ene-1,1-diyl]bis(3-hydroxy-5,5- dimethylcyclohex-2-en-1-one) top
Crystal data top
C25H29NO6Z = 2
Mr = 439.51F(000) = 468.00
Triclinic, P1Dx = 1.256 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71075 Å
a = 9.8306 (14) ÅCell parameters from 5247 reflections
b = 11.0841 (14) Åθ = 3.1–27.5°
c = 11.9602 (13) ŵ = 0.09 mm1
α = 69.601 (3)°T = 298 K
β = 79.867 (4)°Block, colourless
γ = 72.588 (4)°0.20 × 0.10 × 0.10 mm
V = 1161.8 (3) Å3
Data collection top
Rigaku R-AXIS RAPID
diffractometer
1687 reflections with F2 > 2σ(F2)
Detector resolution: 10.000 pixels mm-1Rint = 0.062
ω scansθmax = 25.3°
Absorption correction: multi-scan
(ABSCOR; Rigaku, 1995)
h = 1111
Tmin = 0.657, Tmax = 0.991k = 1313
9400 measured reflectionsl = 1413
4194 independent reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.064Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.191H-atom parameters constrained
S = 0.99 w = 1/[σ2(Fo2) + (0.0813P)2]
where P = (Fo2 + 2Fc2)/3
4194 reflections(Δ/σ)max < 0.001
313 parametersΔρmax = 0.38 e Å3
336 restraintsΔρmin = 0.45 e Å3
Primary atom site location: structure-invariant direct methods
Crystal data top
C25H29NO6γ = 72.588 (4)°
Mr = 439.51V = 1161.8 (3) Å3
Triclinic, P1Z = 2
a = 9.8306 (14) ÅMo Kα radiation
b = 11.0841 (14) ŵ = 0.09 mm1
c = 11.9602 (13) ÅT = 298 K
α = 69.601 (3)°0.20 × 0.10 × 0.10 mm
β = 79.867 (4)°
Data collection top
Rigaku R-AXIS RAPID
diffractometer
4194 independent reflections
Absorption correction: multi-scan
(ABSCOR; Rigaku, 1995)
1687 reflections with F2 > 2σ(F2)
Tmin = 0.657, Tmax = 0.991Rint = 0.062
9400 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.064336 restraints
wR(F2) = 0.191H-atom parameters constrained
S = 0.99Δρmax = 0.38 e Å3
4194 reflectionsΔρmin = 0.45 e Å3
313 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 was performed using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F2. R-factor (gt) are based on 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*/UeqOcc. (<1)
O10.2599 (4)0.9448 (3)0.8416 (3)0.0738 (9)
O20.2544 (4)0.9495 (3)0.4491 (2)0.0659 (8)
O30.3523 (3)0.6854 (3)0.9110 (2)0.0645 (8)
O40.3900 (3)0.6966 (3)0.5114 (2)0.0673 (9)
O5a0.8470 (8)0.5275 (8)0.8424 (8)0.112 (3)0.544 (6)
O51.0123 (10)0.4996 (9)0.8776 (5)0.138 (3)0.456 (6)
O60.8873 (10)0.5826 (9)0.7438 (8)0.105 (3)0.456 (6)
O6a1.0410 (9)0.5912 (8)0.7656 (7)0.131 (3)0.544 (6)
N10.9230 (6)0.6001 (6)0.8254 (5)0.0982 (14)
C10.7340 (5)0.8011 (5)0.8334 (4)0.0613 (10)
C20.8713 (5)0.7226 (5)0.8563 (4)0.0713 (11)
C30.9652 (6)0.7558 (6)0.9076 (5)0.0960 (15)
C40.9227 (7)0.8681 (6)0.9389 (5)0.0977 (16)
C50.7895 (7)0.9491 (6)0.9180 (4)0.0873 (14)
C60.6967 (6)0.9166 (5)0.8660 (4)0.0736 (12)
C70.6299 (5)0.7701 (4)0.7807 (4)0.0585 (10)
C80.5278 (5)0.8605 (4)0.7170 (3)0.0572 (10)
C90.4195 (5)0.8353 (4)0.6577 (3)0.0515 (9)
C100.2823 (4)0.9502 (4)0.6418 (3)0.0520 (10)
C110.2202 (5)1.0022 (4)0.7372 (4)0.0592 (10)
C120.0991 (5)1.1265 (4)0.7155 (4)0.0715 (12)
C130.0902 (5)1.2149 (4)0.5852 (4)0.0638 (11)
C140.0981 (5)1.1248 (4)0.5111 (4)0.0641 (11)
C150.2178 (5)1.0031 (4)0.5369 (4)0.0545 (10)
C160.2137 (6)1.2809 (5)0.5453 (4)0.0798 (13)
C170.0503 (5)1.3220 (5)0.5690 (5)0.0851 (14)
C180.3973 (4)0.6970 (4)0.7065 (3)0.0487 (9)
C190.3753 (4)0.6294 (4)0.8266 (3)0.0520 (10)
C200.3741 (5)0.4871 (4)0.8725 (4)0.0613 (11)
C210.4418 (5)0.4095 (4)0.7843 (4)0.0617 (11)
C220.3813 (5)0.4934 (4)0.6638 (3)0.0624 (11)
C230.3928 (5)0.6342 (4)0.6216 (4)0.0543 (10)
C240.6045 (5)0.3842 (5)0.7714 (4)0.0799 (13)
C250.4058 (6)0.2761 (4)0.8278 (4)0.0862 (14)
H20.30760.87460.47320.0791*
H31.05710.70090.92040.1152*
H3A0.34520.76550.88040.0774*
H40.98470.88990.97470.1172*
H50.76071.02690.93880.1048*
H60.60590.97380.85230.0883*
H70.63650.68090.79310.0702*
H80.52130.94890.70740.0686*
H90.46240.84260.57590.0618*
H12A0.10871.17830.76300.0858*
H12B0.00991.10100.74360.0858*
H14A0.00901.09900.52610.0769*
H14B0.10791.17510.42690.0769*
H16A0.30281.21360.55660.0957*
H16B0.20671.33790.59200.0957*
H16C0.20961.33280.46230.0957*
H17A0.05281.38230.61110.1021*
H17B0.12841.28130.60010.1021*
H17C0.05851.37020.48540.1021*
H20A0.27590.48150.89440.0735*
H20B0.42470.44470.94470.0735*
H22A0.43130.45110.60410.0749*
H22B0.28130.49420.66980.0749*
H24A0.64490.33220.71840.0959*
H24B0.64130.33680.84840.0959*
H24C0.62950.46780.73930.0959*
H25A0.44660.22350.90250.1035*
H25B0.44420.23040.76970.1035*
H25C0.30380.28990.83880.1035*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.089 (3)0.073 (2)0.0583 (16)0.0081 (17)0.0155 (15)0.0260 (14)
O20.080 (3)0.0581 (18)0.0631 (16)0.0145 (16)0.0197 (14)0.0191 (13)
O30.077 (2)0.0698 (18)0.0545 (14)0.0182 (15)0.0097 (13)0.0274 (13)
O40.089 (3)0.0627 (18)0.0494 (15)0.0097 (16)0.0154 (14)0.0203 (13)
O5a0.087 (5)0.107 (5)0.152 (5)0.002 (4)0.028 (5)0.065 (4)
O50.111 (6)0.122 (5)0.174 (6)0.009 (5)0.060 (5)0.047 (5)
O60.092 (5)0.112 (5)0.122 (5)0.004 (4)0.029 (5)0.058 (4)
O6a0.094 (5)0.141 (5)0.130 (5)0.007 (4)0.002 (4)0.044 (4)
N10.069 (3)0.109 (4)0.116 (3)0.001 (3)0.028 (3)0.045 (3)
C10.061 (3)0.072 (3)0.059 (2)0.027 (2)0.0112 (19)0.0192 (19)
C20.056 (3)0.095 (3)0.071 (3)0.025 (3)0.016 (2)0.027 (3)
C30.065 (4)0.134 (5)0.104 (4)0.036 (3)0.023 (3)0.038 (3)
C40.092 (4)0.131 (5)0.098 (4)0.058 (4)0.020 (3)0.037 (3)
C50.102 (4)0.100 (4)0.085 (3)0.050 (3)0.014 (3)0.035 (3)
C60.082 (4)0.081 (3)0.070 (3)0.031 (3)0.016 (3)0.027 (3)
C70.060 (3)0.058 (3)0.064 (3)0.016 (2)0.0126 (19)0.0224 (19)
C80.060 (3)0.056 (3)0.062 (3)0.017 (2)0.0105 (19)0.0217 (18)
C90.053 (3)0.055 (2)0.0522 (19)0.0146 (18)0.0094 (17)0.0205 (16)
C100.051 (3)0.049 (3)0.063 (2)0.0131 (18)0.0088 (18)0.0229 (17)
C110.057 (3)0.057 (3)0.067 (3)0.013 (2)0.008 (2)0.0240 (19)
C120.069 (3)0.060 (3)0.082 (3)0.006 (2)0.001 (2)0.030 (2)
C130.054 (3)0.056 (3)0.081 (3)0.0065 (19)0.014 (2)0.0239 (18)
C140.061 (3)0.056 (3)0.076 (3)0.013 (2)0.023 (2)0.0152 (19)
C150.058 (3)0.047 (3)0.064 (2)0.0163 (19)0.0136 (18)0.0179 (18)
C160.077 (4)0.066 (3)0.104 (3)0.025 (3)0.014 (3)0.028 (3)
C170.073 (4)0.069 (3)0.110 (4)0.003 (3)0.018 (3)0.031 (3)
C180.050 (3)0.048 (2)0.0515 (19)0.0115 (18)0.0107 (17)0.0183 (16)
C190.049 (3)0.056 (3)0.056 (2)0.0114 (19)0.0090 (17)0.0224 (17)
C200.064 (3)0.060 (3)0.060 (2)0.017 (2)0.0070 (19)0.0177 (18)
C210.071 (3)0.049 (2)0.064 (2)0.012 (2)0.0081 (19)0.0177 (17)
C220.074 (3)0.060 (3)0.059 (2)0.018 (3)0.009 (2)0.0244 (18)
C230.058 (3)0.053 (3)0.058 (2)0.0104 (19)0.0155 (18)0.0219 (17)
C240.079 (4)0.075 (3)0.078 (3)0.006 (3)0.008 (3)0.026 (3)
C250.111 (4)0.061 (3)0.087 (3)0.023 (3)0.006 (3)0.022 (3)
Geometric parameters (Å, º) top
O1—C111.259 (5)C21—C241.528 (7)
O2—C151.327 (6)C21—C251.514 (7)
O3—C191.315 (6)C22—C231.497 (6)
O4—C231.257 (4)O2—H20.820
O5a—N11.199 (12)O3—H3A0.820
O5—N11.235 (9)C3—H30.930
O6—N11.186 (14)C4—H40.930
O6a—N11.247 (10)C5—H50.930
N1—C21.453 (9)C6—H60.930
C1—C21.384 (6)C7—H70.930
C1—C61.394 (8)C8—H80.930
C1—C71.467 (8)C9—H90.980
C2—C31.387 (10)C12—H12A0.970
C3—C41.350 (10)C12—H12B0.970
C4—C51.355 (8)C14—H14A0.970
C5—C61.379 (10)C14—H14B0.970
C7—C81.314 (5)C16—H16A0.960
C8—C91.515 (7)C16—H16B0.960
C9—C101.540 (5)C16—H16C0.960
C9—C181.507 (6)C17—H17A0.960
C10—C111.419 (6)C17—H17B0.960
C10—C151.365 (6)C17—H17C0.960
C11—C121.503 (5)C20—H20A0.970
C12—C131.526 (6)C20—H20B0.970
C13—C141.529 (8)C22—H22A0.970
C13—C161.524 (8)C22—H22B0.970
C13—C171.519 (6)C24—H24A0.960
C14—C151.478 (5)C24—H24B0.960
C18—C191.381 (5)C24—H24C0.960
C18—C231.430 (7)C25—H25A0.960
C19—C201.482 (6)C25—H25B0.960
C20—C211.529 (6)C25—H25C0.960
C21—C221.528 (5)
O1···O32.611 (4)H22A···H25A3.5787
O1···C82.855 (5)H22A···H25B2.5392
O1···C92.878 (5)H22A···H25C3.0413
O1···C153.549 (5)H22B···H24A3.5349
O1···C183.476 (5)H22B···H24C3.5669
O1···C193.396 (5)H22B···H25A3.4987
O2···O42.617 (4)H22B···H25B2.8245
O2···C92.908 (5)H22B···H25C2.4356
O2···C183.528 (4)H24A···H25A2.8542
O2···C233.381 (4)H24A···H25B2.4418
O3···C73.126 (5)H24A···H25C3.5079
O3···C83.095 (5)H24B···H25A2.4687
O3···C92.970 (4)H24B···H25B2.9684
O3···C103.527 (4)H24B···H25C3.5347
O3···C113.387 (4)H24C···H25A3.5173
O4···C92.799 (6)H24C···H25B3.5131
O4···C103.485 (6)O1···H4i3.0030
O4···C153.406 (5)O1···H4ii3.5032
O4···C193.564 (5)O1···H5ii2.7182
O5a···C12.871 (10)O2···H6iii3.5246
O5a···C33.438 (13)O2···H8iii2.8634
O5a···C72.840 (8)O2···H14Avii2.7444
O5a···C243.584 (12)O2···H17Bvii3.4098
O5···C13.569 (9)O3···H3i2.8403
O5···C32.877 (13)O3···H20Bviii2.7509
O6···C12.889 (11)O3···H24Bviii2.8118
O6···C33.485 (15)O4···H16Aiii3.3391
O6···C72.832 (10)O4···H17Bvii3.0090
O6a···C13.380 (9)O4···H17Cvii3.5422
O6a···C32.769 (12)O4···H22Aiv2.5841
N1···C72.954 (7)O4···H24Aiv2.9628
C1···C42.808 (10)O4···H25Biv3.4027
C2···C52.714 (9)O5a···H3v3.1383
C3···C62.724 (7)O5a···H16Ciii3.4996
C6···C82.958 (8)O5a···H17Aix3.5217
C7···C182.998 (7)O5a···H20Aviii3.1464
C7···C193.201 (7)O5a···H20Bviii3.3734
C8···C112.973 (6)O5···H3v2.7963
C8···C193.129 (7)O5···H20Avi2.5768
C10···C132.896 (5)O5···H20Aviii3.5819
C10···C163.327 (6)O5···H22Bvi3.2977
C10···C193.413 (5)O5···H25Cvi3.1827
C10···C233.424 (6)O6···H14Biii2.7574
C11···C142.865 (6)O6···H16Ciii2.5568
C11···C163.131 (6)O6···H17Aix3.0218
C11···C183.425 (6)O6···H17Ciii2.9193
C12···C152.828 (7)O6a···H14Biii2.9855
C15···C163.103 (7)O6a···H17Ciii2.8625
C15···C183.409 (5)O6a···H20Avi2.7289
C18···C212.908 (6)O6a···H22Bvi2.5375
C18···C243.350 (6)O6a···H25Cvi3.4915
C19···C222.832 (7)N1···H14Biii3.1675
C19···C243.156 (6)N1···H20Avi3.4593
C20···C232.877 (5)N1···H20Aviii3.5375
C23···C243.101 (5)C1···H14Biii3.1847
O1···C4i3.564 (8)C1···H20Bviii3.5984
O1···C5ii3.378 (7)C1···H25Aviii3.3048
O2···C1iii3.552 (4)C2···H14Biii3.1649
O2···C6iii3.540 (5)C2···H20Aviii3.4410
O2···C8iii3.355 (6)C4···H4x3.5792
O4···C22iv3.530 (5)C4···H12Aii3.3911
O5···O5v2.898 (10)C4···H12Bvi3.0445
O5···N1v3.447 (9)C4···H25Cviii3.4784
O5···C2v3.411 (8)C5···H12Bvi3.1658
O5···C3v3.068 (9)C5···H25Aviii3.4201
O5···C20vi3.509 (12)C5···H25Cviii3.3856
O6···C16iii3.449 (11)C6···H25Aviii2.9999
O6a···C20vi3.446 (10)C6···H25Bxi3.5538
O6a···C22vi3.342 (9)C6···H25Cviii3.4738
N1···O5v3.447 (9)C7···H14Biii3.2878
C1···O2iii3.552 (4)C7···H16Ciii3.4424
C2···O5v3.411 (8)C7···H20Bviii3.3819
C3···O5v3.068 (9)C9···H16Aiii3.4547
C4···O1vi3.564 (8)C11···H4i3.4528
C5···O1ii3.378 (7)C12···H4i3.5531
C6···O2iii3.540 (5)C14···H14Avii3.1557
C8···O2iii3.355 (6)C15···H8iii3.5347
C16···O6iii3.449 (11)C15···H14Avii3.0848
C20···O5i3.509 (12)C16···H9iii3.3562
C20···O6ai3.446 (10)C16···H17Axii3.5465
C22···O4iv3.530 (5)C16···H22Axi3.5359
C22···O6ai3.342 (9)C16···H22Bxi3.4629
O1···H3A1.8342C17···H16Bxii3.5769
O1···H63.5399C17···H16Cxii3.5852
O1···H82.7844C17···H17Axii3.5645
O1···H12A2.5070C17···H22Bvii3.5945
O1···H12B2.7319C17···H24Axiii3.1998
O2···H92.5051C19···H3i3.0945
O2···H14A2.7026C19···H20Bviii3.3743
O2···H14B2.4319C20···H3i3.3994
O3···H72.8942C20···H20Bviii3.5822
O3···H20A2.6639C22···H16Bxiv3.1583
O3···H20B2.4504C22···H17Cvii3.5747
O4···H21.8174C22···H22Aiv3.3566
O4···H92.3403C23···H22Aiv3.2143
O4···H22A2.4877C24···H17Aix3.5690
O4···H22B2.7420C24···H17Bix3.2147
O5a···H72.2686C25···H6xiv3.2801
O5a···H24B3.3115C25···H16Bxiv3.4712
O5a···H24C2.9790H2···H8iii3.0113
O5···H32.6267H2···H14Avii3.0366
O6···H72.4376H2···H17Bvii3.2064
O6···H24C3.1729H3···O3vi2.8403
O6a···H32.5921H3···O5av3.1383
N1···H32.5641H3···O5v2.7963
N1···H72.7408H3···C19vi3.0945
C1···H33.2634H3···C20vi3.3994
C1···H53.2605H3···H3Avi3.0433
C1···H82.5813H3···H20Avi2.7926
C2···H43.2112H3A···H3i3.0433
C2···H63.1880H3A···H4i3.5339
C2···H72.7579H3A···H5ii3.5069
C3···H53.1800H3A···H20Bviii3.1680
C4···H63.2011H3A···H24Bviii3.0533
C5···H33.1824H4···O1vi3.0030
C6···H43.2121H4···O1ii3.5032
C6···H73.2603H4···C4x3.5792
C6···H82.6468H4···C11vi3.4528
C7···H3A2.8506H4···C12vi3.5531
C7···H62.6167H4···H3Avi3.5339
C7···H92.9336H4···H4x2.8184
C7···H24C3.5544H4···H5x3.3384
C8···H3A2.5711H4···H12Aii3.0006
C8···H62.6862H4···H12Bvi2.9619
C9···H22.4829H4···H12Bii3.4153
C9···H3A2.5386H5···O1ii2.7182
C9···H72.6835H5···H3Aii3.5069
C10···H22.3880H5···H4x3.3384
C10···H3A2.9169H5···H12Bvi3.1592
C10···H82.6008H5···H24Axi3.4969
C10···H12A3.2426H5···H24Bxi3.1287
C10···H12B3.0073H5···H25Axi3.2026
C10···H14A2.9856H6···O2iii3.5246
C10···H14B3.2068H6···C25xi3.2801
C10···H16A2.7945H6···H25Axi2.9513
C11···H3A2.6463H6···H25Aviii3.0533
C11···H82.8233H6···H25Bxi2.7351
C11···H93.2808H7···H14Biii3.5952
C11···H14A3.2339H7···H16Ciii3.1934
C11···H16A2.7944H7···H20Bviii2.9886
C11···H16B3.4867H8···O2iii2.8634
C12···H14A2.7122H8···C15iii3.5347
C12···H14B3.2924H8···H2iii3.0113
C12···H16A2.6627H8···H9iii3.3798
C12···H16B2.7033H8···H25Bxi3.2971
C12···H16C3.3288H9···C16iii3.3562
C12···H17A2.7355H9···H8iii3.3798
C12···H17B2.6436H9···H9iii3.5603
C12···H17C3.3293H9···H16Aiii2.6017
C14···H23.0444H9···H16Ciii3.2761
C14···H12A3.2916H12A···C4ii3.3911
C14···H12B2.7082H12A···H4ii3.0006
C14···H16A2.6932H12A···H25Bxi3.5332
C14···H16B3.3344H12A···H25Cxi2.9740
C14···H16C2.6837H12B···C4i3.0445
C14···H17A3.3171H12B···C5i3.1658
C14···H17B2.6918H12B···H4i2.9619
C14···H17C2.6349H12B···H4ii3.4153
C15···H92.5344H12B···H5i3.1592
C15···H12B3.1990H14A···O2vii2.7444
C15···H16A2.7950H14A···C14vii3.1557
C15···H16C3.4246H14A···C15vii3.0848
C16···H12A2.6131H14A···H2vii3.0366
C16···H12B3.3222H14A···H14Avii2.5426
C16···H14A3.3289H14A···H14Bvii3.3968
C16···H14B2.6213H14B···O6iii2.7574
C16···H17A2.6225H14B···O6aiii2.9855
C16···H17B3.3104H14B···N1iii3.1675
C16···H17C2.6927H14B···C1iii3.1847
C17···H12A2.7523H14B···C2iii3.1649
C17···H12B2.5912H14B···C7iii3.2878
C17···H14A2.5751H14B···H7iii3.5952
C17···H14B2.7287H14B···H14Avii3.3968
C17···H16A3.3107H16A···O4iii3.3391
C17···H16B2.6519H16A···C9iii3.4547
C17···H16C2.6645H16A···H9iii2.6017
C18···H22.9046H16A···H22Axi3.4848
C18···H3A2.3784H16A···H25Bxi3.1936
C18···H72.6666H16B···C17xii3.5769
C18···H83.3684H16B···C22xi3.1583
C18···H20A3.0331H16B···C25xi3.4712
C18···H20B3.2050H16B···H17Axii3.3232
C18···H22A3.2670H16B···H17Cxii3.0023
C18···H22B2.9904H16B···H22Axi2.8937
C18···H24C2.8224H16B···H22Bxi2.5559
C19···H72.7270H16B···H25Bxi3.1152
C19···H93.2664H16B···H25Cxi3.0826
C19···H22B3.1642H16C···O5aiii3.4996
C19···H24B3.4641H16C···O6iii2.5568
C19···H24C2.8724H16C···C7iii3.4424
C20···H3A3.0466H16C···C17xii3.5852
C20···H22A3.3016H16C···H7iii3.1934
C20···H22B2.7055H16C···H9iii3.2761
C20···H24A3.3430H16C···H17Axii2.9580
C20···H24B2.6842H16C···H17Cxii3.4087
C20···H24C2.7197H16C···H24Ciii3.1993
C20···H25A2.6991H17A···O5axiii3.5217
C20···H25B3.3242H17A···O6xiii3.0218
C20···H25C2.6521H17A···C16xii3.5465
C22···H20A2.7423H17A···C17xii3.5645
C22···H20B3.2959H17A···C24xiii3.5690
C22···H24A2.7098H17A···H16Bxii3.3232
C22···H24B3.3286H17A···H16Cxii2.9580
C22···H24C2.6519H17A···H17Axii3.2813
C22···H25A3.3247H17A···H17Cxii3.0329
C22···H25B2.6657H17A···H24Axiii3.1522
C22···H25C2.6881H17A···H24Cxiii3.2490
C23···H22.6153H17B···O2vii3.4098
C23···H92.4571H17B···O4vii3.0090
C23···H20A3.2901H17B···C24xiii3.2147
C23···H24A3.4684H17B···H2vii3.2064
C23···H24C2.7518H17B···H22Bvii3.5698
C24···H73.4968H17B···H24Axiii2.4454
C24···H20A3.3332H17B···H24Bxiii3.5206
C24···H20B2.6149H17B···H24Cxiii3.2810
C24···H22A2.6186H17C···O4vii3.5422
C24···H22B3.3259H17C···O6iii2.9193
C24···H25A2.6254H17C···O6aiii2.8625
C24···H25B2.6517H17C···C22vii3.5747
C24···H25C3.3017H17C···H16Bxii3.0023
C25···H20A2.5714H17C···H16Cxii3.4087
C25···H20B2.7563H17C···H17Axii3.0329
C25···H22A2.7239H17C···H17Cxii3.5419
C25···H22B2.6024H17C···H22Bvii2.8316
C25···H24A2.6166H20A···O5aviii3.1464
C25···H24B2.6679H20A···O5i2.5768
C25···H24C3.2985H20A···O5viii3.5819
H2···H91.9955H20A···O6ai2.7289
H2···H14A3.3585H20A···N1i3.4593
H2···H14B3.2310H20A···N1viii3.5375
H3···H42.2832H20A···C2viii3.4410
H3A···H72.8629H20A···H3i2.7926
H3A···H83.0536H20B···O3viii2.7509
H3A···H93.5015H20B···O5aviii3.3734
H3A···H20A3.3586H20B···C1viii3.5984
H3A···H20B3.2391H20B···C7viii3.3819
H4···H52.2837H20B···C19viii3.3743
H5···H62.2902H20B···C20viii3.5822
H6···H73.4744H20B···H3Aviii3.1680
H6···H82.1787H20B···H7viii2.9886
H7···H82.7253H20B···H20Bviii2.8907
H7···H93.0610H22A···O4iv2.5841
H7···H24C2.6782H22A···C16xiv3.5359
H8···H92.4936H22A···C22iv3.3566
H8···H16A3.2218H22A···C23iv3.2143
H12A···H16A2.8289H22A···H16Axiv3.4848
H12A···H16B2.4577H22A···H16Bxiv2.8937
H12A···H16C3.5099H22A···H22Aiv2.6484
H12A···H17A2.6336H22B···O5i3.2977
H12A···H17B2.9976H22B···O6ai2.5375
H12B···H14A2.6107H22B···C16xiv3.4629
H12B···H16A3.5761H22B···C17vii3.5945
H12B···H16B3.5225H22B···H16Bxiv2.5559
H12B···H17A2.8916H22B···H17Bvii3.5698
H12B···H17B2.3643H22B···H17Cvii2.8316
H12B···H17C3.4639H24A···O4iv2.9628
H14A···H16C3.5119H24A···C17ix3.1998
H14A···H17A3.4831H24A···H5xiv3.4969
H14A···H17B2.4259H24A···H17Aix3.1522
H14A···H17C2.7595H24A···H17Bix2.4454
H14B···H16A2.8728H24B···O3viii2.8118
H14B···H16B3.5081H24B···H3Aviii3.0533
H14B···H16C2.4376H24B···H5xiv3.1287
H14B···H17A3.5723H24B···H17Bix3.5206
H14B···H17B3.0739H24C···H16Ciii3.1993
H14B···H17C2.5258H24C···H17Aix3.2490
H16A···H17A3.5041H24C···H17Bix3.2810
H16A···H17C3.5631H25A···C1viii3.3048
H16B···H17A2.4337H25A···C5viii3.4201
H16B···H17B3.5119H25A···C6viii2.9999
H16B···H17C2.9736H25A···H5xiv3.2026
H16C···H17A2.8886H25A···H6xiv2.9513
H16C···H17B3.5546H25A···H6viii3.0533
H16C···H17C2.5226H25B···O4iv3.4027
H20A···H22B2.6318H25B···C6xiv3.5538
H20A···H24B3.4999H25B···H6xiv2.7351
H20A···H25A2.8273H25B···H8xiv3.2971
H20A···H25B3.4607H25B···H12Axiv3.5332
H20A···H25C2.3657H25B···H16Axiv3.1936
H20B···H24A3.4986H25B···H16Bxiv3.1152
H20B···H24B2.4210H25C···O5i3.1827
H20B···H24C2.8781H25C···O6ai3.4915
H20B···H25A2.6110H25C···C4viii3.4784
H20B···H25C3.0365H25C···C5viii3.3856
H22A···H24A2.4715H25C···C6viii3.4738
H22A···H24B3.5179H25C···H12Axiv2.9740
H22A···H24C2.8237H25C···H16Bxiv3.0826
O5a—N1—O6a125.1 (8)C4—C3—H3120.118
O5a—N1—C2120.9 (6)C3—C4—H4120.071
O5—N1—O6109.5 (8)C5—C4—H4120.073
O5—N1—C2125.8 (7)C4—C5—H5119.828
O6—N1—C2124.8 (6)C6—C5—H5119.829
O6a—N1—C2113.2 (7)C1—C6—H6118.852
C2—C1—C6114.9 (5)C5—C6—H6118.851
C2—C1—C7125.1 (5)C1—C7—H7117.990
C6—C1—C7120.0 (4)C8—C7—H7117.987
N1—C2—C1120.0 (6)C7—C8—H8116.681
N1—C2—C3117.2 (5)C9—C8—H8116.681
C1—C2—C3122.8 (6)C8—C9—H9104.325
C2—C3—C4119.8 (5)C10—C9—H9104.329
C3—C4—C5119.9 (7)C18—C9—H9104.333
C4—C5—C6120.3 (6)C11—C12—H12A108.529
C1—C6—C5122.3 (5)C11—C12—H12B108.526
C1—C7—C8124.0 (5)C13—C12—H12A108.527
C7—C8—C9126.6 (5)C13—C12—H12B108.526
C8—C9—C10110.9 (4)H12A—C12—H12B107.525
C8—C9—C18115.7 (3)C13—C14—H14A108.795
C10—C9—C18115.6 (4)C13—C14—H14B108.793
C9—C10—C11120.0 (4)C15—C14—H14A108.798
C9—C10—C15121.1 (4)C15—C14—H14B108.791
C11—C10—C15118.9 (4)H14A—C14—H14B107.676
O1—C11—C10122.0 (4)C13—C16—H16A109.467
O1—C11—C12118.4 (4)C13—C16—H16B109.470
C10—C11—C12119.6 (4)C13—C16—H16C109.467
C11—C12—C13115.0 (4)H16A—C16—H16B109.471
C12—C13—C14106.9 (4)H16A—C16—H16C109.476
C12—C13—C16110.3 (4)H16B—C16—H16C109.476
C12—C13—C17110.8 (4)C13—C17—H17A109.468
C14—C13—C16110.4 (4)C13—C17—H17B109.474
C14—C13—C17109.3 (5)C13—C17—H17C109.466
C16—C13—C17109.2 (4)H17A—C17—H17B109.480
C13—C14—C15113.8 (4)H17A—C17—H17C109.469
O2—C15—C10123.5 (4)H17B—C17—H17C109.471
O2—C15—C14113.4 (4)C19—C20—H20A108.639
C10—C15—C14123.1 (4)C19—C20—H20B108.629
C9—C18—C19124.7 (4)C21—C20—H20A108.630
C9—C18—C23117.2 (3)C21—C20—H20B108.629
C19—C18—C23118.0 (4)H20A—C20—H20B107.589
O3—C19—C18123.3 (4)C21—C22—H22A108.682
O3—C19—C20113.5 (3)C21—C22—H22B108.674
C18—C19—C20123.2 (4)C23—C22—H22A108.681
C19—C20—C21114.5 (3)C23—C22—H22B108.684
C20—C21—C22107.3 (3)H22A—C22—H22B107.597
C20—C21—C24110.9 (5)C21—C24—H24A109.474
C20—C21—C25110.2 (4)C21—C24—H24B109.470
C22—C21—C24109.8 (4)C21—C24—H24C109.471
C22—C21—C25110.3 (5)H24A—C24—H24B109.476
C24—C21—C25108.3 (4)H24A—C24—H24C109.472
C21—C22—C23114.3 (5)H24B—C24—H24C109.464
O4—C23—C18121.7 (4)C21—C25—H25A109.470
O4—C23—C22118.2 (4)C21—C25—H25B109.471
C18—C23—C22120.0 (3)C21—C25—H25C109.468
C15—O2—H2109.474H25A—C25—H25B109.474
C19—O3—H3A109.472H25A—C25—H25C109.471
C2—C3—H3120.105H25B—C25—H25C109.474
O5a—N1—C2—C140.8 (8)C9—C10—C15—O210.0 (7)
O5a—N1—C2—C3139.7 (7)C9—C10—C15—C14171.3 (4)
O5—N1—C2—C1150.3 (7)C11—C10—C15—O2169.7 (4)
O5—N1—C2—C330.3 (9)C11—C10—C15—C149.1 (7)
O6—N1—C2—C131.3 (9)C15—C10—C11—O1168.3 (4)
O6—N1—C2—C3148.1 (7)C15—C10—C11—C129.1 (7)
O6a—N1—C2—C1129.2 (6)O1—C11—C12—C13160.1 (4)
O6a—N1—C2—C350.3 (7)C10—C11—C12—C1322.4 (7)
C2—C1—C6—C50.5 (6)C11—C12—C13—C1449.9 (6)
C6—C1—C2—N1179.5 (3)C11—C12—C13—C1670.2 (5)
C6—C1—C2—C30.1 (6)C11—C12—C13—C17168.8 (4)
C2—C1—C7—C8151.8 (4)C12—C13—C14—C1549.6 (5)
C7—C1—C2—N11.3 (6)C16—C13—C14—C1570.3 (4)
C7—C1—C2—C3179.2 (3)C17—C13—C14—C15169.6 (3)
C6—C1—C7—C829.1 (6)C13—C14—C15—O2158.6 (4)
C7—C1—C6—C5178.7 (3)C13—C14—C15—C1022.5 (6)
N1—C2—C3—C4179.6 (4)C9—C18—C19—O39.4 (6)
C1—C2—C3—C41.0 (7)C9—C18—C19—C20171.1 (3)
C2—C3—C4—C51.2 (7)C9—C18—C23—O48.4 (6)
C3—C4—C5—C60.6 (7)C9—C18—C23—C22175.7 (3)
C4—C5—C6—C10.2 (7)C19—C18—C23—O4169.0 (4)
C1—C7—C8—C9178.3 (3)C19—C18—C23—C226.9 (5)
C7—C8—C9—C10154.4 (4)C23—C18—C19—O3167.8 (4)
C7—C8—C9—C1820.2 (6)C23—C18—C19—C2011.7 (6)
C8—C9—C10—C1145.0 (5)O3—C19—C20—C21163.2 (3)
C8—C9—C10—C15135.3 (4)C18—C19—C20—C2117.3 (6)
C8—C9—C18—C1948.0 (5)C19—C20—C21—C2247.1 (5)
C8—C9—C18—C23134.9 (3)C19—C20—C21—C2472.9 (4)
C10—C9—C18—C1984.1 (5)C19—C20—C21—C25167.2 (4)
C10—C9—C18—C2393.1 (4)C20—C21—C22—C2351.6 (5)
C18—C9—C10—C1189.3 (5)C24—C21—C22—C2369.1 (5)
C18—C9—C10—C1590.4 (4)C25—C21—C22—C23171.6 (3)
C9—C10—C11—O111.4 (7)C21—C22—C23—O4157.5 (4)
C9—C10—C11—C12171.2 (4)C21—C22—C23—C1826.5 (5)
Symmetry codes: (i) x1, y, z; (ii) x+1, y+2, z+2; (iii) x+1, y+2, z+1; (iv) x+1, y+1, z+1; (v) x+2, y+1, z+2; (vi) x+1, y, z; (vii) x, y+2, z+1; (viii) x+1, y+1, z+2; (ix) x+1, y1, z; (x) x+2, y+2, z+2; (xi) x, y+1, z; (xii) x, y+3, z+1; (xiii) x1, y+1, z; (xiv) x, y1, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2···O40.821.822.617 (4)165
O3—H3A···O10.821.832.611 (4)158
C16—H16C···O6iii0.962.563.449 (11)155
C20—H20A···O5i0.972.583.509 (12)161
C22—H22A···O4iv0.972.583.530 (5)165
C22—H22B···O6ai0.972.543.342 (9)140
Symmetry codes: (i) x1, y, z; (iii) x+1, y+2, z+1; (iv) x+1, y+1, z+1.

Experimental details

Crystal data
Chemical formulaC25H29NO6
Mr439.51
Crystal system, space groupTriclinic, P1
Temperature (K)298
a, b, c (Å)9.8306 (14), 11.0841 (14), 11.9602 (13)
α, β, γ (°)69.601 (3), 79.867 (4), 72.588 (4)
V3)1161.8 (3)
Z2
Radiation typeMo Kα
µ (mm1)0.09
Crystal size (mm)0.20 × 0.10 × 0.10
Data collection
DiffractometerRigaku R-AXIS RAPID
Absorption correctionMulti-scan
(ABSCOR; Rigaku, 1995)
Tmin, Tmax0.657, 0.991
No. of measured, independent and
observed [F2 > 2σ(F2)] reflections
9400, 4194, 1687
Rint0.062
(sin θ/λ)max1)0.600
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.064, 0.191, 0.99
No. of reflections4194
No. of parameters313
No. of restraints336
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.38, 0.45

Computer programs: RAPID AUTO (Rigaku, 2006), IL MILIONE (Burla et al., 2007), SHELXL97 (Sheldrick, 2008), CrystalStructure (Rigaku, 2010).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2···O40.8201.8172.617 (4)164.5
O3—H3A···O10.8201.8342.611 (4)157.7
C16—H16C···O6i0.9602.5573.449 (11)155.0
C20—H20A···O5ii0.9702.5773.509 (12)161.0
C22—H22A···O4iii0.9702.5843.530 (5)165.0
C22—H22B···O6aii0.9702.5383.342 (9)140.0
Symmetry codes: (i) x+1, y+2, z+1; (ii) x1, y, z; (iii) x+1, y+1, z+1.
 

Acknowledgements

The authors gratefully thank Dr Hiroyasu Sato (SCX and BioSAXS Group, Rigaku Corporation) for helpful comments. Fiancial support from the Korea Institute of Science and Technology (KIST) is gratefully acknowledged.

References

First citationBolte, M., Degen, A. & Rühl, S. (2001). Acta Cryst. C57, 446–451.  Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
First citationBurla, M. C., Caliandro, R., Camalli, M., Carrozzini, B., Cascarano, G. L., De Caro, L., Giacovazzo, C., Polidori, G., Siliqi, D. & Spagna, R. (2007). J. Appl. Cryst. 40, 609–613.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationCha, J. H., Son, M. H., Min, S.-J., Cho, Y. S. & Lee, J. K. (2011). Acta Cryst. E67, o2739.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationPalakshi Reddy, B., Vijayakumar, V., Sarveswari, S., Ng, S. W. & Tiekink, E. R. T. (2010). Acta Cryst. E66, o2806–o2807.  Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
First citationRigaku (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.  Google Scholar
First citationRigaku (2006). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan.  Google Scholar
First citationRigaku (2010). CrystalStructure. 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 citationZhu, Y.-L., Xiao, G.-L., Chen, Y.-F., Chen, R.-T. & Zhou, Y. (2011). Acta Cryst. E67, o2398.  Web of Science CSD CrossRef 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