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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 70| Part 4| April 2014| Pages o400-o401

Methyl 3,5-bis­(cyclo­hexyl­meth­­oxy)benzoate

aDepartment of Chemistry, Fordham University, 441 East Fordham Road, Bronx, NY 10458, USA
*Correspondence e-mail: pcorfield@fordham.edu

(Received 26 February 2014; accepted 27 February 2014; online 8 March 2014)

In the title compound, C22H32O4, the atoms of the methyl ester group and the alk­oxy O atoms are all coplanar with the central aromatic ring, with an r.m.s. deviation of 0.008 Å. Bonds to the methyl­ene and cyclo­hexyl groups are also very close to this plane, so that the mol­ecule is essentially flat, apart from the cyclo­hexyl groups. The mean planes through the cyclo­hexyl groups are tilted by 30.08 (9) and 36.14 (7)° with respect to the central aromatic ring. In the crystal, pairs of mol­ecules linked by C—H⋯O hydrogen bonds form planar units which are stacked along the a axis, with an average inter­planar distance of 3.549 (2) Å. Stacking appears to be stabilized by further weak C—H⋯O hydrogen bonds.

Related literature

The title compound was synthesized as a monomer for novel dendrimers, as part of a continuing study of how dendrimers effectively complex with organic pollutants in aqueous environments. For a project review, see: Monaco et al. (2013[Monaco, D. N., Tomas, S. C., Kirrane, M. K. & Balija, A. M. (2013). Beilstein J. Org. Chem. 9, 2320-2327.]); Corfield & Balija (2013[Corfield, P. W. R. & Balija, A. M. (2013). Acta Cryst. E69, o1822-o1823.]). For a review of the role of C—H⋯O hydrogen bonds in organic reactions, see: Johnston & Cheong (2013[Johnston, R. C. & Cheong, P. H.-Y. (2013). Org. Biomol. Chem. 11, 5057-5064.]). For an example of an organic crystal structure involving the cyclo­hexyl­meth­oxy­benzene fragment, see: Yang et al. (2008[Yang, J., Qi, Q.-R., Huang, W.-C. & Zheng, H. (2008). Acta Cryst. E64, o741.]).

[Scheme 1]

Experimental

Crystal data
  • C22H32O4

  • Mr = 360.48

  • Triclinic, [P \overline 1]

  • a = 6.649 (1) Å

  • b = 12.668 (1) Å

  • c = 12.873 (1) Å

  • α = 87.64 (1)°

  • β = 79.46 (1)°

  • γ = 75.06 (1)°

  • V = 1029.9 (2) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.08 mm−1

  • T = 298 K

  • 0.75 × 0.75 × 0.53 mm

Data collection
  • Enraf–Nonius CAD-4 diffractometer

  • 5155 measured reflections

  • 4051 independent reflections

  • 3013 reflections with I > 2σ(I)

  • Rint = 0.008

  • 3 standard reflections every 120 min intensity decay: 1.3 (5)%

Refinement
  • R[F2 > 2σ(F2)] = 0.044

  • wR(F2) = 0.128

  • S = 1.03

  • 4051 reflections

  • 237 parameters

  • H-atom parameters constrained

  • Δρmax = 0.17 e Å−3

  • Δρmin = −0.14 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C8—H8B⋯O4i 0.96 2.58 3.409 (2) 145
C16—H16A⋯O3ii 0.97 2.71 3.573 (2) 148
C18—H18A⋯O3ii 0.97 2.72 3.590 (2) 149
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) -x, -y+1, -z+1.

Data collection: CAD-4 (Enraf–Nonius, 1994[Enraf-Nonius (1994). CAD-4. Enraf-Nonius, Delft, The Netherlands.]); cell refinement: CAD-4; data reduction: followed procedures in Corfield et al. (1973[Corfield, P. W. R., Dabrowiak, J. C. & Gore, E. S. (1973). Inorg. Chem. 12, 1734-1740.]) and data were averaged with a local version of SORTAV (Blessing, 1989[Blessing, R. H. (1989). J. Appl. Cryst. 22, 396-397.]); 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: ORTEPIII (Burnett & Johnson, 1996[Burnett, M. N. & Johnson, C. K. (1996). ORTEPIII. Report ORNL-6895. Oak Ridge National Laboratory, Tennessee, USA.]); software used to prepare material for publication: SHELXL97.

Supporting information


Experimental top

Synthesis and crystallization top

The reaction was performed under an argon gas atmosphere with oven dried glassware. Reagents were obtained from Aldrich and used without further purification. Eluent solvent ratios are reported in v/v.

1H NMR spectra were recorded at 300 MHz and 13C NMR spectra were recorded at 75 MHz on a Bruker AV-300 High Performance Digital NMR Spectrometer. Chemical shifts are reported in parts per million (ppm) and coupling constants in Hertz (Hz). 1H NMR spectra obtained in CDCl3 were referenced to 7.26 ppm and 13C NMR spectra obtained in CDCl3 were referenced to 77.2 ppm. Mass spectra were obtained from University of Illinois Mass Spectrometry Center (Micromass Q-TOF Ultra, ESI).

To a heterogeneous mixture of 8.50 g (61.5 mmol) of K2CO3 in DMF (37.5 mL) were added 5.00 g (29.7 mmol) of methyl 3,5-di­hydroxy benzoate. After 2 hours, 8.80 mL (63.1 mmol) of bromo­methyl­cyclo­hexane were added over 10 min and the reaction heated at 80oC for 3 h. Upon cooling the reaction to room temperature, ethyl acetate (100 mL) was added and the organic layer was washed with water (5X, 70 mL) and brine (1X, 70 mL). The organic layer was dried with anhydrous sodium sulfate and the solvent was removed in vacuo. The resulting mixture of methyl 3-cyclo­hexyl­meth­oxy-5-hy­droxy­benzoate and methyl 3,5-bis­(cyclo­hexyl­meth­oxy)­benzoate was separated by column chromatography (silica gel, petroleum ether:di­ethyl ether, 1:1). The title product was obtained as a yellow oil and allowed to sit undisturbed over several months, when colorless crystals separated, mp 70.6-72.8°C.

1H NMR peaks δ: 7.15 (d, J = 2.3, 2H), 6.63 (t, J = 2.3, 1H), 3.91 (s, 3H), 3.77 (d, J = 6.2, 4H), 1.88-1.03 (m, 22H). 13C NMR peaks δ: 167.00, 160.6, 132.0, 107.9, 107.0, 73.8, 52.3, 37.6, 29.8, 26.5, 25.8. HRMS-ESI: m/z [M + H]+ C22H33O4 361.2390; found 361.2379.

Refinement top

Both forms of the 0 1 0 and of the 0 0 1 reflections were partially obscured by the beam stop, and were omitted from the refinements. H atoms were constrained to idealized positions with C—H distances of 0.93Å for the aromatic H atoms, 0.96Å for the methyl H atoms, 0.97Å for the secondary H atoms and 0.98Å for the tertiary H atoms on C10 and C17. The orientation of the methyl group was determined by calculation of electron density in the toroid that should contain the H atoms of the idealized methyl group. The Ueq values for all H atoms were fixed at 1.2 times the Uiso of their bonded C atoms.

Comment top

Dendrimers are macromolecules prepared in a stepwise fashion from monomer units and a core molecule. This work is part of a larger study examining how the the modification of functional groups in the monomer impacts the physical and chemical properties of the resulting dendrimer. The title compound is an inter­mediate for a novel cyclo­hexane based dendrimer (Monaco et al., 2013; Corfield and Balija, 2013).

In the title compound, C22H32O4, the four atoms of the methyl ester group and the two oxygen atoms of the 3,5 alk­oxy substituents are all coplanar with the central aromatic ring, with a dihedral angle of the ester group to the ring of only 0.7 (1)°. Bonds to the cyclo­hexyl groups are also close to this plane, with torsional angles C2—C3—O1—C9 and C3—O1—C9—C10 of 172.88 (15)° and 179.66 (14)° respectively, and C6—C5—O2—C16 and C5—O2—C16—C17 angles of 3.4 (3)° and 175.59 (14)° respectively. The C10—C15 and C17—C22 cyclo­hexyl groups are oriented respectively away from and towards the methyl ester group on C1 (Fig. 1), and their mean planes are tilted 30.08 (9)° and 36.14 (7)° to the central aromatic ring. A similar extended conformation for the cyclo­hexyl­meth­oxy substituent in a related compound is found in Yang et al. (2008).

Steric repulsion between methyl­ene hydrogen atoms of the alk­oxy groups and ring protons leads to opening of the exterior ring angles to 124.6 (1)° and 24.8 (1)°, and of the bond angles at the ether oxygen atoms to 118.7 (1)° and 117.9 (1)°.

Pairs of molecules are connected by weak C—H··· O hydrogen bonds across the center of symmetry at (1 - x, 1 - y, 1 - z). (Figs. 2 and 3) The central planes of the symmetry-related molecules are almost coplanar, with a perpendicular distance between them of 0.105 (3)Å. The molecular pairs are stacked along the a axis, with average inter­planar spacing of 3.549 (2) Å. (Fig. 4) There are no obvious ππ inter­actions to explain the short stacking distance. We propose that part of the inter­planar inter­action arises from the presence of long C—H···O hydrogen bonds between O3 and methyl­ene and cyclo­hexyl hydrogen atoms H16A and H18A. (See Table 1) Such non-classical hydrogen bonds are frequently invoked in recent publications in this journal, and their impact on reaction stereochemistry is reviewed in Johnston and Cheong (2013).

Related literature top

The title compound was synthesized as a monomer for novel dendrimers, as part of a continuing study of how dendrimers effectively complex with organic pollutants in aqueous environments. For a project review, see: Monaco et al. (2013); Corfield & Balija (2013). For a review of the role of C—H···O hydrogen bonds in organic reactions, see: Johnston & Cheong (2013). For an example of an organic crystal structure involving the cyclohexylmethoxybenzene fragment, see: Yang et al. (2008).

Computing details top

Data collection: CAD-4 (Enraf–Nonius, 1994); cell refinement: CAD-4 (Enraf–Nonius, 1994); data reduction: followed procedures in Corfield et al. (1973) and data were averaged with a local version of SORTAV (Blessing, 1989); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPIII (Burnett & Johnson, 1996); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title molecule, with ellipsoids at the 50% level.
[Figure 2] Fig. 2. Packing of the title complex, viewed along the a* axis, with ellipsoid outlines at 30% probability. Proposed hydrogen bonds are shown as dashed lines. Hydrogen bonds from O3, C16A and C18A are to molecules translated by -a.
[Figure 3] Fig. 3. View of the hydrogen-bonded pair of molecules perpendicular to the central molecular plane. The dashed molecules represent a molecular pair unit translated by -a.
[Figure 4] Fig. 4. Stacking of molecular pairs related by translations along the a axis. The dashed lines represent the proposed long C—H···O hydrogen bonds. This figure is related to Fig. 3 by rotation of 90° about the horizontal axis.
Methyl 3,5-bis(cyclohexylmethoxy)benzoate top
Crystal data top
C22H32O4Z = 2
Mr = 360.48F(000) = 392
Triclinic, P1Dx = 1.162 Mg m3
Hall symbol: -P 1Melting point: 344.8 K
a = 6.649 (1) ÅMo Kα radiation, λ = 0.71070 Å
b = 12.668 (1) ÅCell parameters from 25 reflections
c = 12.873 (1) Åθ = 3.2–9.7°
α = 87.64 (1)°µ = 0.08 mm1
β = 79.46 (1)°T = 298 K
γ = 75.06 (1)°Block, colourless
V = 1029.9 (2) Å30.75 × 0.75 × 0.53 mm
Data collection top
Enraf–Nonius CAD-4
diffractometer
Rint = 0.008
Radiation source: fine-focus sealed tubeθmax = 26.0°, θmin = 2.3°
Graphite monochromatorh = 18
θ/2θ scansk = 1515
5155 measured reflectionsl = 1515
4051 independent reflections3 standard reflections every 120 min
3013 reflections with I > 2σ(I) intensity decay: 1.3(5)
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.044H-atom parameters constrained
wR(F2) = 0.128 w = 1/[σ2(Fo2) + (0.033P)2 + 0.270P]
where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max = 0.002
4051 reflectionsΔρmax = 0.17 e Å3
237 parametersΔρmin = 0.14 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.011 (2)
Crystal data top
C22H32O4γ = 75.06 (1)°
Mr = 360.48V = 1029.9 (2) Å3
Triclinic, P1Z = 2
a = 6.649 (1) ÅMo Kα radiation
b = 12.668 (1) ŵ = 0.08 mm1
c = 12.873 (1) ÅT = 298 K
α = 87.64 (1)°0.75 × 0.75 × 0.53 mm
β = 79.46 (1)°
Data collection top
Enraf–Nonius CAD-4
diffractometer
Rint = 0.008
5155 measured reflections3 standard reflections every 120 min
4051 independent reflections intensity decay: 1.3(5)
3013 reflections with I > 2σ(I)
Refinement top
R[F2 > 2σ(F2)] = 0.0440 restraints
wR(F2) = 0.128H-atom parameters constrained
S = 1.03Δρmax = 0.17 e Å3
4051 reflectionsΔρmin = 0.14 e Å3
237 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
O10.2343 (2)0.20265 (10)0.34241 (8)0.0613 (3)
O20.0616 (2)0.25640 (11)0.67501 (8)0.0628 (4)
O30.2878 (2)0.42136 (12)0.25302 (9)0.0756 (4)
O40.37753 (19)0.44700 (10)0.40594 (8)0.0602 (3)
C10.1250 (2)0.34685 (12)0.40804 (11)0.0450 (4)
C20.0091 (3)0.30219 (13)0.35244 (11)0.0486 (4)
H20.02170.31180.27970.058*
C30.1264 (3)0.24282 (13)0.40479 (11)0.0490 (4)
C40.1455 (3)0.22817 (14)0.51302 (12)0.0512 (4)
H40.23550.18780.54820.061*
C50.0280 (3)0.27471 (13)0.56870 (11)0.0495 (4)
C60.1076 (3)0.33363 (13)0.51749 (11)0.0485 (4)
H60.18620.36410.55490.058*
C70.2697 (3)0.40810 (13)0.34645 (12)0.0483 (4)
C80.5185 (3)0.50921 (17)0.35207 (14)0.0655 (5)
H8A0.60790.46830.29220.079*
H8B0.60420.52360.39950.079*
H8C0.43720.57710.32860.079*
C90.3584 (3)0.13030 (15)0.38765 (12)0.0554 (4)
H9A0.46550.16610.44590.067*
H9B0.26920.06580.41450.067*
C100.4621 (3)0.09842 (14)0.30275 (12)0.0516 (4)
H100.54360.16570.27460.062*
C110.3030 (3)0.03691 (16)0.21158 (14)0.0621 (5)
H11A0.21140.08230.17950.075*
H11B0.21570.02860.23790.075*
C120.4151 (4)0.00567 (19)0.12867 (16)0.0777 (6)
H12A0.31100.03770.07350.093*
H12B0.48940.07140.09670.093*
C130.5711 (4)0.05892 (19)0.17717 (19)0.0862 (7)
H13A0.64630.07330.12370.103*
H13B0.49460.12860.20160.103*
C140.7281 (4)0.00134 (19)0.26845 (18)0.0795 (6)
H14A0.81900.04440.30050.095*
H14B0.81630.06700.24280.095*
C150.6158 (3)0.03203 (17)0.35076 (15)0.0665 (5)
H15A0.71970.07420.40670.080*
H15B0.53950.03390.38160.080*
C160.0433 (3)0.30659 (15)0.73897 (11)0.0525 (4)
H16A0.00980.38490.72760.063*
H16B0.19530.27780.72000.063*
C170.0299 (3)0.28262 (14)0.85363 (11)0.0500 (4)
H170.00380.20320.86260.060*
C180.2652 (3)0.32768 (16)0.88989 (12)0.0571 (4)
H18A0.30250.40590.87840.069*
H18B0.34110.29490.84820.069*
C190.3324 (3)0.3047 (2)1.00661 (13)0.0713 (6)
H19A0.48220.33851.02810.086*
H19B0.31010.22651.01670.086*
C200.2097 (3)0.3479 (2)1.07503 (13)0.0755 (6)
H20A0.24800.42711.07290.091*
H20B0.24730.32591.14760.091*
C210.0244 (3)0.3063 (2)1.03912 (14)0.0855 (7)
H21A0.06580.22811.05110.103*
H21B0.09760.34091.08070.103*
C220.0908 (3)0.3291 (2)0.92233 (13)0.0706 (6)
H22A0.06490.40730.91170.085*
H22B0.24130.29690.90100.085*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0823 (8)0.0788 (8)0.0403 (6)0.0437 (7)0.0227 (6)0.0013 (5)
O20.0878 (9)0.0868 (9)0.0294 (5)0.0490 (7)0.0117 (5)0.0017 (5)
O30.1073 (11)0.0992 (10)0.0400 (7)0.0588 (9)0.0200 (6)0.0126 (6)
O40.0700 (8)0.0812 (8)0.0408 (6)0.0389 (7)0.0108 (5)0.0017 (5)
C10.0534 (9)0.0468 (8)0.0358 (7)0.0132 (7)0.0093 (6)0.0030 (6)
C20.0623 (10)0.0546 (9)0.0326 (7)0.0175 (8)0.0140 (7)0.0004 (6)
C30.0596 (10)0.0563 (9)0.0364 (7)0.0190 (8)0.0150 (7)0.0059 (7)
C40.0612 (10)0.0616 (10)0.0379 (8)0.0272 (8)0.0092 (7)0.0034 (7)
C50.0618 (10)0.0586 (10)0.0311 (7)0.0193 (8)0.0094 (6)0.0058 (6)
C60.0580 (9)0.0581 (10)0.0349 (7)0.0208 (8)0.0122 (7)0.0056 (6)
C70.0581 (9)0.0508 (9)0.0376 (8)0.0144 (7)0.0108 (7)0.0023 (6)
C80.0700 (12)0.0821 (13)0.0543 (10)0.0387 (10)0.0084 (9)0.0001 (9)
C90.0628 (10)0.0688 (11)0.0424 (8)0.0274 (9)0.0130 (7)0.0026 (8)
C100.0554 (9)0.0567 (10)0.0491 (9)0.0192 (8)0.0186 (7)0.0024 (7)
C110.0644 (11)0.0728 (12)0.0551 (10)0.0219 (9)0.0170 (8)0.0115 (8)
C120.0951 (15)0.0896 (15)0.0598 (11)0.0326 (12)0.0261 (11)0.0183 (10)
C130.1146 (18)0.0749 (14)0.0933 (16)0.0410 (13)0.0549 (14)0.0056 (12)
C140.0806 (14)0.0876 (15)0.0923 (16)0.0464 (12)0.0389 (12)0.0143 (12)
C150.0657 (12)0.0796 (13)0.0647 (11)0.0324 (10)0.0199 (9)0.0060 (10)
C160.0600 (10)0.0700 (11)0.0344 (8)0.0261 (8)0.0110 (7)0.0060 (7)
C170.0632 (10)0.0591 (10)0.0320 (7)0.0201 (8)0.0122 (7)0.0030 (6)
C180.0603 (10)0.0788 (12)0.0414 (8)0.0310 (9)0.0132 (7)0.0013 (8)
C190.0726 (12)0.1068 (16)0.0428 (9)0.0418 (12)0.0042 (8)0.0003 (9)
C200.0836 (14)0.1131 (17)0.0355 (9)0.0389 (13)0.0022 (8)0.0136 (9)
C210.0782 (14)0.148 (2)0.0381 (9)0.0345 (14)0.0178 (9)0.0129 (11)
C220.0581 (11)0.1212 (17)0.0398 (9)0.0323 (11)0.0101 (8)0.0153 (10)
Geometric parameters (Å, º) top
O1—C31.3608 (17)C12—H12A0.9700
O1—C91.4245 (19)C12—H12B0.9700
O2—C51.3658 (18)C13—C141.506 (3)
O2—C161.4322 (17)C13—H13A0.9700
O3—C71.1959 (18)C13—H13B0.9700
O4—C71.3256 (18)C14—C151.518 (2)
O4—C81.4415 (19)C14—H14A0.9700
C1—C21.373 (2)C14—H14B0.9700
C1—C61.399 (2)C15—H15A0.9700
C1—C71.487 (2)C15—H15B0.9700
C2—C31.385 (2)C16—C171.511 (2)
C2—H20.9300C16—H16A0.9700
C3—C41.385 (2)C16—H16B0.9700
C4—C51.396 (2)C17—C221.523 (2)
C4—H40.9300C17—C181.512 (2)
C5—C61.376 (2)C17—H170.9800
C6—H60.9300C18—C191.526 (2)
C8—H8A0.9600C18—H18A0.9700
C8—H8B0.9600C18—H18B0.9700
C8—H8C0.9600C19—C201.508 (2)
C9—C101.513 (2)C19—H19A0.9700
C9—H9A0.9700C19—H19B0.9700
C9—H9B0.9700C20—C211.499 (3)
C10—C151.518 (2)C20—H20A0.9700
C10—C111.516 (2)C20—H20B0.9700
C10—H100.9800C21—C221.525 (2)
C11—C121.526 (2)C21—H21A0.9700
C11—H11A0.9700C21—H21B0.9700
C11—H11B0.9700C22—H22A0.9700
C12—C131.514 (3)C22—H22B0.9700
C3—O1—C9118.71 (12)C14—C13—H13B109.3
C5—O2—C16117.86 (12)C12—C13—H13B109.3
C7—O4—C8116.24 (12)H13A—C13—H13B107.9
C2—C1—C6120.88 (14)C13—C14—C15110.87 (17)
C2—C1—C7116.97 (13)C13—C14—H14A109.5
C6—C1—C7122.15 (13)C15—C14—H14A109.5
C1—C2—C3119.89 (14)C13—C14—H14B109.5
C1—C2—H2120.1C15—C14—H14B109.5
C3—C2—H2120.1H14A—C14—H14B108.1
O1—C3—C4124.58 (14)C10—C15—C14111.39 (16)
O1—C3—C2115.13 (13)C10—C15—H15A109.3
C4—C3—C2120.28 (14)C14—C15—H15A109.3
C3—C4—C5119.23 (15)C10—C15—H15B109.3
C3—C4—H4120.4C14—C15—H15B109.3
C5—C4—H4120.4H15A—C15—H15B108.0
O2—C5—C6124.79 (13)O2—C16—C17108.62 (13)
O2—C5—C4114.21 (14)O2—C16—H16A110.0
C6—C5—C4121.00 (13)C17—C16—H16A110.0
C5—C6—C1118.70 (14)O2—C16—H16B110.0
C5—C6—H6120.6C17—C16—H16B110.0
C1—C6—H6120.6H16A—C16—H16B108.3
O3—C7—O4123.11 (15)C16—C17—C22109.33 (14)
O3—C7—C1123.90 (14)C16—C17—C18113.02 (14)
O4—C7—C1112.99 (12)C22—C17—C18109.76 (13)
O4—C8—H8A109.5C16—C17—H17108.2
O4—C8—H8B109.5C22—C17—H17108.2
H8A—C8—H8B109.5C18—C17—H17108.2
O4—C8—H8C109.5C19—C18—C17111.55 (15)
H8A—C8—H8C109.5C19—C18—H18A109.3
H8B—C8—H8C109.5C17—C18—H18A109.3
O1—C9—C10108.22 (13)C19—C18—H18B109.3
O1—C9—H9A110.1C17—C18—H18B109.3
C10—C9—H9A110.1H18A—C18—H18B108.0
O1—C9—H9B110.1C20—C19—C18111.71 (15)
C10—C9—H9B110.1C20—C19—H19A109.3
H9A—C9—H9B108.4C18—C19—H19A109.3
C9—C10—C15109.83 (14)C20—C19—H19B109.3
C9—C10—C11112.77 (14)C18—C19—H19B109.3
C15—C10—C11110.74 (15)H19A—C19—H19B107.9
C9—C10—H10107.8C21—C20—C19111.69 (16)
C15—C10—H10107.8C21—C20—H20A109.3
C11—C10—H10107.8C19—C20—H20A109.3
C12—C11—C10110.79 (15)C21—C20—H20B109.3
C12—C11—H11A109.5C19—C20—H20B109.3
C10—C11—H11A109.5H20A—C20—H20B107.9
C12—C11—H11B109.5C20—C21—C22111.75 (17)
C10—C11—H11B109.5C20—C21—H21A109.3
H11A—C11—H11B108.1C22—C21—H21A109.3
C11—C12—C13111.22 (17)C20—C21—H21B109.3
C11—C12—H12A109.4C22—C21—H21B109.3
C13—C12—H12A109.4H21A—C21—H21B107.9
C11—C12—H12B109.4C17—C22—C21111.58 (16)
C13—C12—H12B109.4C17—C22—H22A109.3
H12A—C12—H12B108.0C21—C22—H22A109.3
C14—C13—C12111.78 (17)C17—C22—H22B109.3
C14—C13—H13A109.3C21—C22—H22B109.3
C12—C13—H13A109.3H22A—C22—H22B108.0
C2—C3—O1—C9172.88 (15)C4—C5—O2—C16176.46 (15)
C4—C3—O1—C97.4 (3)C6—C5—O2—C163.3 (3)
C3—O1—C9—C10179.66 (14)C5—O2—C16—C17175.59 (14)
O1—C9—C10—C1162.55 (19)O2—C16—C17—C1861.10 (19)
O1—C9—C10—C15173.41 (15)O2—C16—C17—C22176.33 (15)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C8—H8B···O4i0.962.583.409 (2)145
C16—H16A···O3ii0.972.713.573 (2)148
C18—H18A···O3ii0.972.723.590 (2)149
Symmetry codes: (i) x+1, y+1, z+1; (ii) x, y+1, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C8—H8B···O4i0.962.583.409 (2)145.2
C16—H16A···O3ii0.972.713.573 (2)147.9
C18—H18A···O3ii0.972.723.590 (2)149.4
Symmetry codes: (i) x+1, y+1, z+1; (ii) x, y+1, z+1.
 

Acknowledgements

We are grateful for the Dean's Office at Fordham University for its generous financial support. We thank Matthew P. Tracey for his assistance with this work. The Q-Tof Ultima mass spectrometer (University of Illinois at Urbana-Champaign) was purchased in part with a grant from the NSF, Division of Biological Infrastructure (DBI-0100085).

References

First citationBlessing, R. H. (1989). J. Appl. Cryst. 22, 396–397.  CrossRef Web of Science IUCr Journals Google Scholar
First citationBurnett, M. N. & Johnson, C. K. (1996). ORTEPIII. Report ORNL-6895. Oak Ridge National Laboratory, Tennessee, USA.  Google Scholar
First citationCorfield, P. W. R. & Balija, A. M. (2013). Acta Cryst. E69, o1822–o1823.  CSD CrossRef CAS IUCr Journals Google Scholar
First citationCorfield, P. W. R., Dabrowiak, J. C. & Gore, E. S. (1973). Inorg. Chem. 12, 1734–1740.  CSD CrossRef CAS Web of Science Google Scholar
First citationEnraf–Nonius (1994). CAD-4. Enraf–Nonius, Delft, The Netherlands.  Google Scholar
First citationJohnston, R. C. & Cheong, P. H.-Y. (2013). Org. Biomol. Chem. 11, 5057–5064.  Web of Science CrossRef CAS PubMed Google Scholar
First citationMonaco, D. N., Tomas, S. C., Kirrane, M. K. & Balija, A. M. (2013). Beilstein J. Org. Chem. 9, 2320–2327.  Web of Science CrossRef PubMed Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationYang, J., Qi, Q.-R., Huang, W.-C. & Zheng, H. (2008). Acta Cryst. E64, o741.  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
Volume 70| Part 4| April 2014| Pages o400-o401
Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds