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

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ISSN: 2056-9890

10-(2-Hy­dr­oxy­eth­yl)-9-(2-hy­dr­oxy­phen­yl)-3,3,6,6-tetra­methyl-1,2,3,4,5,6,7,8,9,10-deca­hydro­acridine-1,8-dione

aDepartment of Organic Chemistry, Baku State University, Baku, Azerbaijan, bSchool of Biology, Chemistry and Material Science, Manchester Metropolitan University, Manchester, England, and cDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
*Correspondence e-mail: seikweng@um.edu.my

(Received 16 February 2011; accepted 23 February 2011; online 26 February 2011)

The dihydro­pyridine ring in the title compound, C25H31NO4, adopts an envelope conformation with the methine C atom representing the flap. The cyclo­hexenone rings also adopt envelope conformations with the C atoms bearing the methyl C atoms representing the flaps. The phenolic hy­droxy group forms an intra­molecular hydrogen bond to one of the two keto O atoms. The hy­droxy group of the N-bonded alkyl chain forms an inter­molecular hydrogen bond to the other keto O atom of an adjacent mol­ecule. The latter hydrogen bond leads to the formation of a helical chain running along the b axis.

Related literature

For a related structure, see: Jang et al. (2005[Jang, H., Li, T., Tu, S. & Zou, X. (2005). Acta Cryst. E61, o2296-o2298.]).

[Scheme 1]

Experimental

Crystal data
  • C25H31NO4

  • Mr = 409.51

  • Monoclinic, P 21 /n

  • a = 9.7037 (2) Å

  • b = 16.5123 (3) Å

  • c = 13.8847 (3) Å

  • β = 102.132 (3)°

  • V = 2175.06 (8) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.08 mm−1

  • T = 100 K

  • 0.25 × 0.20 × 0.15 mm

Data collection
  • Agilent SuperNova Dual diffractometer with an Atlas detector

  • Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010[Agilent (2010). CrysAlis PRO. Agilent Technologies, Yarnton, England.]) Tmin = 0.979, Tmax = 0.988

  • 19082 measured reflections

  • 4915 independent reflections

  • 3770 reflections with I > 2σ(I)

  • Rint = 0.042

Refinement
  • R[F2 > 2σ(F2)] = 0.048

  • wR(F2) = 0.123

  • S = 1.03

  • 4915 reflections

  • 279 parameters

  • 2 restraints

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.27 e Å−3

  • Δρmin = −0.26 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O1—H1⋯O2 0.84 (1) 1.84 (1) 2.659 (2) 166 (2)
O4—H4⋯O3i 0.85 (1) 1.98 (1) 2.818 (2) 166 (2)
Symmetry code: (i) [-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{3\over 2}}].

Data collection: CrysAlis PRO (Agilent, 2010[Agilent (2010). CrysAlis PRO. Agilent Technologies, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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: X-SEED (Barbour, 2001[Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.]); software used to prepare material for publication: publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).

Supporting information


Comment top

Substituted benzaldehydes react with dimedone along with a primary amine to yield N-substituted 1,2,3,4,5,6,7,8,9,10-decahydro-acridine-1,8-diones. The title compound has a hydroxy group in 2-position of the aromatic ring. This permits intramolecular hydrogen bonding, a feature also noted in the related 9-(2,6-dihydroxyphenyl)-3,3,6,6-tetramethyl-N-(4-methylphenyl)-1,8-dioxo-1,2,3,4,5,6,7,8,9,10-decahydroacridine (Jang et al., 2005). The second hydroxy unit in this case engages in intermolecular hydrogen bonding to afford a centrosymmetric dimer. The title compound (Scheme I, Fig. 1) has another hydroxy unit in the N bonded hydroxyethyl substituent. This groups engages in intermolecular hydrogen bond furnishing a linear chain that runs along the c-axis of the monoclinic unit cell.

Related literature top

For a related structure, see: Jang et al. (2005).

Experimental top

Dimedone (20 mmol), salicylic aldehyde (10 mmol) and 2-amino-ethanol (10 mmol) were heated in ethanol (100 ml) for 5 h. After cooling the solution the product was collected by filtration and crystallized from ethanol; m.p. 462 K.

Refinement top

Carbon-bound H-atoms were placed in calculated positions [C—H 0.95 to 0.98 Å, Uiso(H) 1.2 to 1.5Ueq(C)] and were included in the refinement in the riding model approximation.

The hydroxy H-atoms were located in a difference Fourier map, and were refined with a distance restraint of O–H 0.84±0.01 Å; their temperature factors were refined.

Computing details top

Data collection: CrysAlis PRO (Agilent, 2010); cell refinement: CrysAlis PRO (Agilent, 2010); data reduction: CrysAlis PRO (Agilent, 2010); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top
[Figure 1] Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of C25H31NO4 at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.
10-(2-Hydroxyethyl)-9-(2-hydroxyphenyl)-3,3,6,6-tetramethyl- 1,2,3,4,5,6,7,8,9,10-decahydroacridine-1,8-dione top
Crystal data top
C25H31NO4F(000) = 880
Mr = 409.51Dx = 1.251 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 6079 reflections
a = 9.7037 (2) Åθ = 2.3–29.4°
b = 16.5123 (3) ŵ = 0.08 mm1
c = 13.8847 (3) ÅT = 100 K
β = 102.132 (3)°Irregular block, light yellow
V = 2175.06 (8) Å30.25 × 0.20 × 0.15 mm
Z = 4
Data collection top
Agilent SuperNova Dual
diffractometer with an Atlas detector
4915 independent reflections
Radiation source: SuperNova (Mo) X-ray Source3770 reflections with I > 2σ(I)
Mirror monochromatorRint = 0.042
Detector resolution: 10.4041 pixels mm-1θmax = 27.5°, θmin = 2.4°
ω scansh = 1212
Absorption correction: multi-scan
(CrysAlis PRO; Agilent, 2010)
k = 2121
Tmin = 0.979, Tmax = 0.988l = 1818
19082 measured reflections
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)] = 0.048Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.123H atoms treated by a mixture of independent and constrained refinement
S = 1.03 w = 1/[σ2(Fo2) + (0.0517P)2 + 0.8053P]
where P = (Fo2 + 2Fc2)/3
4915 reflections(Δ/σ)max = 0.001
279 parametersΔρmax = 0.27 e Å3
2 restraintsΔρmin = 0.26 e Å3
Crystal data top
C25H31NO4V = 2175.06 (8) Å3
Mr = 409.51Z = 4
Monoclinic, P21/nMo Kα radiation
a = 9.7037 (2) ŵ = 0.08 mm1
b = 16.5123 (3) ÅT = 100 K
c = 13.8847 (3) Å0.25 × 0.20 × 0.15 mm
β = 102.132 (3)°
Data collection top
Agilent SuperNova Dual
diffractometer with an Atlas detector
4915 independent reflections
Absorption correction: multi-scan
(CrysAlis PRO; Agilent, 2010)
3770 reflections with I > 2σ(I)
Tmin = 0.979, Tmax = 0.988Rint = 0.042
19082 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0482 restraints
wR(F2) = 0.123H atoms treated by a mixture of independent and constrained refinement
S = 1.03Δρmax = 0.27 e Å3
4915 reflectionsΔρmin = 0.26 e Å3
279 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.48778 (12)0.25598 (7)0.49186 (8)0.0245 (3)
O20.71758 (12)0.26499 (7)0.63474 (8)0.0239 (3)
O30.32877 (12)0.07916 (7)0.64843 (8)0.0252 (3)
O40.36042 (14)0.44954 (8)0.90598 (10)0.0357 (3)
N10.45983 (13)0.28498 (7)0.88782 (9)0.0174 (3)
C10.37807 (16)0.29121 (9)0.52419 (11)0.0198 (3)
C20.28360 (17)0.33708 (10)0.45699 (12)0.0242 (4)
H20.29800.34430.39190.029*
C30.16843 (17)0.37236 (10)0.48466 (12)0.0245 (4)
H30.10300.40300.43820.029*
C40.14843 (17)0.36311 (9)0.57997 (12)0.0232 (4)
H4A0.07010.38780.59930.028*
C50.24353 (16)0.31759 (9)0.64673 (11)0.0201 (3)
H50.22970.31180.71210.024*
C60.35895 (16)0.28008 (9)0.62057 (11)0.0181 (3)
C70.46282 (16)0.22884 (9)0.69374 (11)0.0173 (3)
H70.50660.18840.65570.021*
C80.57885 (16)0.27978 (9)0.75365 (11)0.0182 (3)
C90.70525 (17)0.29325 (9)0.71557 (11)0.0195 (3)
C100.82323 (16)0.34044 (9)0.77743 (12)0.0212 (3)
H10A0.88260.36370.73440.025*
H10B0.88280.30340.82470.025*
C110.76993 (17)0.40884 (9)0.83440 (12)0.0216 (3)
C120.67029 (16)0.37278 (9)0.89612 (11)0.0204 (3)
H12A0.72780.34680.95540.024*
H12B0.61670.41750.91860.024*
C130.56744 (16)0.31146 (9)0.84253 (11)0.0173 (3)
C140.69201 (19)0.47206 (10)0.76251 (13)0.0298 (4)
H14A0.75630.49450.72360.045*
H14B0.65810.51560.79950.045*
H14C0.61170.44650.71840.045*
C150.89404 (18)0.44878 (10)0.90356 (13)0.0273 (4)
H15A0.95750.47260.86490.041*
H15B0.94520.40810.94870.041*
H15C0.85920.49130.94150.041*
C160.43798 (17)0.32332 (9)0.97968 (11)0.0204 (3)
H16A0.52660.35001.01310.025*
H16B0.41540.28081.02430.025*
C170.32055 (19)0.38537 (10)0.96141 (12)0.0266 (4)
H17A0.23230.36020.92490.032*
H17B0.30390.40601.02490.032*
C180.38348 (16)0.21533 (9)0.85240 (11)0.0169 (3)
C190.29342 (16)0.17702 (9)0.91636 (11)0.0195 (3)
H19A0.23810.22000.94050.023*
H19B0.35590.15230.97450.023*
C200.19150 (17)0.11202 (9)0.86392 (11)0.0203 (3)
C210.27110 (18)0.05689 (9)0.80557 (12)0.0236 (4)
H21A0.34880.02920.85140.028*
H21B0.20630.01500.77080.028*
C220.33022 (16)0.10522 (9)0.73201 (11)0.0193 (3)
C230.39203 (16)0.18370 (9)0.76380 (11)0.0179 (3)
C240.13741 (18)0.06237 (10)0.94152 (13)0.0259 (4)
H24A0.08830.09810.97950.039*
H24B0.21720.03650.98590.039*
H24C0.07220.02070.90880.039*
C250.06713 (17)0.15154 (10)0.79316 (12)0.0238 (4)
H25A0.10230.18350.74390.036*
H25B0.01620.18700.83030.036*
H25C0.00330.10940.76000.036*
H10.5572 (17)0.2508 (14)0.5393 (12)0.051 (7)*
H40.2939 (18)0.4842 (11)0.8949 (16)0.053 (7)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0232 (6)0.0345 (7)0.0163 (6)0.0009 (5)0.0056 (5)0.0008 (5)
O20.0219 (6)0.0323 (6)0.0188 (6)0.0007 (5)0.0074 (5)0.0029 (5)
O30.0310 (7)0.0246 (6)0.0225 (6)0.0054 (5)0.0110 (5)0.0070 (5)
O40.0373 (8)0.0282 (7)0.0454 (8)0.0109 (6)0.0175 (6)0.0102 (6)
N10.0183 (7)0.0202 (6)0.0141 (6)0.0011 (5)0.0040 (5)0.0022 (5)
C10.0210 (8)0.0203 (8)0.0181 (7)0.0056 (6)0.0041 (6)0.0021 (6)
C20.0262 (9)0.0266 (8)0.0181 (8)0.0098 (7)0.0009 (7)0.0014 (7)
C30.0218 (8)0.0229 (8)0.0244 (8)0.0047 (7)0.0049 (7)0.0027 (7)
C40.0208 (8)0.0212 (8)0.0261 (8)0.0010 (7)0.0013 (7)0.0031 (7)
C50.0213 (8)0.0196 (8)0.0190 (8)0.0039 (6)0.0034 (6)0.0027 (6)
C60.0191 (8)0.0170 (7)0.0170 (7)0.0059 (6)0.0007 (6)0.0024 (6)
C70.0186 (8)0.0193 (7)0.0151 (7)0.0003 (6)0.0057 (6)0.0021 (6)
C80.0184 (8)0.0186 (7)0.0174 (7)0.0020 (6)0.0036 (6)0.0015 (6)
C90.0201 (8)0.0203 (8)0.0182 (8)0.0035 (6)0.0039 (6)0.0024 (6)
C100.0187 (8)0.0245 (8)0.0204 (8)0.0006 (7)0.0044 (6)0.0013 (7)
C110.0209 (8)0.0203 (8)0.0230 (8)0.0012 (6)0.0029 (7)0.0004 (7)
C120.0193 (8)0.0219 (8)0.0191 (8)0.0024 (6)0.0020 (6)0.0032 (6)
C130.0167 (8)0.0174 (7)0.0172 (7)0.0039 (6)0.0024 (6)0.0012 (6)
C140.0313 (10)0.0240 (8)0.0322 (9)0.0013 (7)0.0021 (8)0.0045 (7)
C150.0231 (9)0.0280 (9)0.0305 (9)0.0042 (7)0.0048 (7)0.0041 (7)
C160.0243 (8)0.0234 (8)0.0144 (7)0.0007 (7)0.0058 (6)0.0040 (6)
C170.0338 (10)0.0248 (8)0.0244 (8)0.0055 (7)0.0132 (7)0.0010 (7)
C180.0154 (7)0.0170 (7)0.0179 (7)0.0033 (6)0.0026 (6)0.0010 (6)
C190.0218 (8)0.0223 (8)0.0152 (7)0.0017 (6)0.0059 (6)0.0003 (6)
C200.0220 (8)0.0204 (8)0.0201 (8)0.0011 (6)0.0080 (7)0.0008 (6)
C210.0286 (9)0.0186 (8)0.0257 (8)0.0004 (7)0.0105 (7)0.0003 (7)
C220.0188 (8)0.0201 (7)0.0196 (7)0.0026 (6)0.0057 (6)0.0005 (6)
C230.0179 (8)0.0185 (7)0.0176 (7)0.0025 (6)0.0047 (6)0.0004 (6)
C240.0299 (9)0.0240 (8)0.0268 (8)0.0012 (7)0.0127 (7)0.0031 (7)
C250.0208 (8)0.0281 (8)0.0230 (8)0.0031 (7)0.0058 (7)0.0000 (7)
Geometric parameters (Å, º) top
O1—C11.3690 (19)C12—C131.504 (2)
O1—H10.841 (10)C12—H12A0.9900
O2—C91.2442 (18)C12—H12B0.9900
O3—C221.2349 (18)C14—H14A0.9800
O4—C171.411 (2)C14—H14B0.9800
O4—H40.852 (9)C14—H14C0.9800
N1—C131.3975 (19)C15—H15A0.9800
N1—C181.400 (2)C15—H15B0.9800
N1—C161.4785 (18)C15—H15C0.9800
C1—C21.388 (2)C16—C171.514 (2)
C1—C61.401 (2)C16—H16A0.9900
C2—C31.384 (2)C16—H16B0.9900
C2—H20.9500C17—H17A0.9900
C3—C41.386 (2)C17—H17B0.9900
C3—H30.9500C18—C231.355 (2)
C4—C51.384 (2)C18—C191.510 (2)
C4—H4A0.9500C19—C201.535 (2)
C5—C61.393 (2)C19—H19A0.9900
C5—H50.9500C19—H19B0.9900
C6—C71.528 (2)C20—C241.532 (2)
C7—C231.502 (2)C20—C211.531 (2)
C7—C81.508 (2)C20—C251.533 (2)
C7—H71.0000C21—C221.502 (2)
C8—C131.366 (2)C21—H21A0.9900
C8—C91.451 (2)C21—H21B0.9900
C9—C101.497 (2)C22—C231.457 (2)
C10—C111.530 (2)C24—H24A0.9800
C10—H10A0.9900C24—H24B0.9800
C10—H10B0.9900C24—H24C0.9800
C11—C151.524 (2)C25—H25A0.9800
C11—C141.530 (2)C25—H25B0.9800
C11—C121.540 (2)C25—H25C0.9800
C1—O1—H1109.6 (16)H14A—C14—H14C109.5
C17—O4—H4108.6 (15)H14B—C14—H14C109.5
C13—N1—C18119.28 (12)C11—C15—H15A109.5
C13—N1—C16120.69 (12)C11—C15—H15B109.5
C18—N1—C16119.57 (12)H15A—C15—H15B109.5
O1—C1—C2117.44 (14)C11—C15—H15C109.5
O1—C1—C6121.71 (14)H15A—C15—H15C109.5
C2—C1—C6120.83 (15)H15B—C15—H15C109.5
C3—C2—C1120.06 (15)N1—C16—C17112.62 (13)
C3—C2—H2120.0N1—C16—H16A109.1
C1—C2—H2120.0C17—C16—H16A109.1
C2—C3—C4120.13 (16)N1—C16—H16B109.1
C2—C3—H3119.9C17—C16—H16B109.1
C4—C3—H3119.9H16A—C16—H16B107.8
C5—C4—C3119.46 (15)O4—C17—C16108.47 (13)
C5—C4—H4A120.3O4—C17—H17A110.0
C3—C4—H4A120.3C16—C17—H17A110.0
C4—C5—C6121.74 (15)O4—C17—H17B110.0
C4—C5—H5119.1C16—C17—H17B110.0
C6—C5—H5119.1H17A—C17—H17B108.4
C5—C6—C1117.76 (14)C23—C18—N1120.45 (13)
C5—C6—C7121.80 (13)C23—C18—C19121.74 (14)
C1—C6—C7120.43 (14)N1—C18—C19117.81 (12)
C23—C7—C8108.04 (12)C18—C19—C20114.13 (12)
C23—C7—C6112.22 (12)C18—C19—H19A108.7
C8—C7—C6111.70 (12)C20—C19—H19A108.7
C23—C7—H7108.2C18—C19—H19B108.7
C8—C7—H7108.3C20—C19—H19B108.7
C6—C7—H7108.2H19A—C19—H19B107.6
C13—C8—C9120.37 (14)C24—C20—C21109.84 (13)
C13—C8—C7121.27 (13)C24—C20—C25109.79 (13)
C9—C8—C7118.35 (13)C21—C20—C25109.31 (13)
O2—C9—C8121.33 (14)C24—C20—C19108.81 (13)
O2—C9—C10120.38 (14)C21—C20—C19108.68 (13)
C8—C9—C10118.27 (13)C25—C20—C19110.39 (13)
C9—C10—C11112.33 (13)C22—C21—C20110.56 (13)
C9—C10—H10A109.1C22—C21—H21A109.5
C11—C10—H10A109.1C20—C21—H21A109.5
C9—C10—H10B109.1C22—C21—H21B109.5
C11—C10—H10B109.1C20—C21—H21B109.5
H10A—C10—H10B107.9H21A—C21—H21B108.1
C15—C11—C14109.44 (14)O3—C22—C23121.15 (14)
C15—C11—C10109.70 (13)O3—C22—C21121.56 (14)
C14—C11—C10109.92 (13)C23—C22—C21117.28 (13)
C15—C11—C12108.79 (13)C18—C23—C22121.21 (13)
C14—C11—C12110.17 (13)C18—C23—C7121.36 (14)
C10—C11—C12108.80 (12)C22—C23—C7117.42 (13)
C13—C12—C11114.45 (12)C20—C24—H24A109.5
C13—C12—H12A108.6C20—C24—H24B109.5
C11—C12—H12A108.6H24A—C24—H24B109.5
C13—C12—H12B108.6C20—C24—H24C109.5
C11—C12—H12B108.6H24A—C24—H24C109.5
H12A—C12—H12B107.6H24B—C24—H24C109.5
C8—C13—N1119.79 (14)C20—C25—H25A109.5
C8—C13—C12122.23 (13)C20—C25—H25B109.5
N1—C13—C12117.95 (13)H25A—C25—H25B109.5
C11—C14—H14A109.5C20—C25—H25C109.5
C11—C14—H14B109.5H25A—C25—H25C109.5
H14A—C14—H14B109.5H25B—C25—H25C109.5
C11—C14—H14C109.5
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O20.84 (1)1.84 (1)2.659 (2)166 (2)
O4—H4···O3i0.85 (1)1.98 (1)2.818 (2)166 (2)
Symmetry code: (i) x+1/2, y+1/2, z+3/2.

Experimental details

Crystal data
Chemical formulaC25H31NO4
Mr409.51
Crystal system, space groupMonoclinic, P21/n
Temperature (K)100
a, b, c (Å)9.7037 (2), 16.5123 (3), 13.8847 (3)
β (°) 102.132 (3)
V3)2175.06 (8)
Z4
Radiation typeMo Kα
µ (mm1)0.08
Crystal size (mm)0.25 × 0.20 × 0.15
Data collection
DiffractometerAgilent SuperNova Dual
diffractometer with an Atlas detector
Absorption correctionMulti-scan
(CrysAlis PRO; Agilent, 2010)
Tmin, Tmax0.979, 0.988
No. of measured, independent and
observed [I > 2σ(I)] reflections
19082, 4915, 3770
Rint0.042
(sin θ/λ)max1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.048, 0.123, 1.03
No. of reflections4915
No. of parameters279
No. of restraints2
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.27, 0.26

Computer programs: CrysAlis PRO (Agilent, 2010), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O20.84 (1)1.84 (1)2.659 (2)166 (2)
O4—H4···O3i0.85 (1)1.98 (1)2.818 (2)166 (2)
Symmetry code: (i) x+1/2, y+1/2, z+3/2.
 

Acknowledgements

We thank Manchester Metropolitan University, Baku State University and the University of Malaya for supporting this study.

References

First citationAgilent (2010). CrysAlis PRO. Agilent Technologies, Yarnton, England.  Google Scholar
First citationBarbour, L. J. (2001). J. Supramol. Chem. 1, 189–191.  CrossRef CAS Google Scholar
First citationJang, H., Li, T., Tu, S. & Zou, X. (2005). Acta Cryst. E61, o2296–o2298.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationWestrip, S. P. (2010). J. Appl. Cryst. 43, 920–925.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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