PMCCPMCCPMCC

Search tips
Search criteria 

Advanced

 
Logo of actaeInternational Union of Crystallographysearchopen accessarticle submissionjournal home pagethis article
 
Acta Crystallogr Sect E Struct Rep Online. 2010 January 1; 66(Pt 1): o219–o220.
Published online 2009 December 24. doi:  10.1107/S1600536809054129
PMCID: PMC2980072

2-{[(4-Methoxy­phen­yl)dimethyl­silyl]meth­yl}isoindoline-1,3-dione

Abstract

In the course of our studies of silicon-containing anti­cancer compounds, the title compound, C18H19NO3Si, was synthesized. The mol­ecular geometry including bond distances and angles involving the Si atoms are typical. Torsion angles associated with the isoindoline ring and the silyl group [C—N—Cmethyl­ene—Si = 90.5 (2) and −93.1 (2)°] indicate that there is no inter­action between the O and Si atoms despite silicon’s high affinity for oxygen.

Related literature

For literature related to drug design see: Bains & Tacke (2003 [triangle]); Bikzhanova et al. (2007 [triangle]); Franz (2007 [triangle]); Franz et al. (2007 [triangle]); Gately & West (2007 [triangle]); Guzei, Spencer, Zakai & Lynch (2010 [triangle]); Guzei, Spencer & Zakai (2010 [triangle]); Latxague & Leger (2004 [triangle]); Lee et al. (1993 [triangle], 1996 [triangle]); Murai et al. (1998 [triangle]); Showell & Mills (2003 [triangle]); Tacke & Zilch (1986 [triangle]); Tsuge et al. (1985 [triangle]); Yoon et al. (1991 [triangle], 1992 [triangle], 1997 [triangle]). For a description of the Cambridge Structural Database, see: Allen (2002 [triangle]). Bond distances and angles were confirmed to be typical by a Mogul structural check (Bruno et al., 2004 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-0o219-scheme1.jpg

Experimental

Crystal data

  • C18H19NO3Si
  • M r = 325.43
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-0o219-efi1.jpg
  • a = 10.2713 (16) Å
  • b = 14.061 (3) Å
  • c = 12.069 (2) Å
  • β = 103.355 (6)°
  • V = 1695.9 (5) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.15 mm−1
  • T = 300 K
  • 0.50 × 0.40 × 0.23 mm

Data collection

  • Bruker SMART X2S diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2009 [triangle]) T min = 0.928, T max = 0.966
  • 11394 measured reflections
  • 3197 independent reflections
  • 2338 reflections with I > 2σ(I)
  • R int = 0.042

Refinement

  • R[F 2 > 2σ(F 2)] = 0.046
  • wR(F 2) = 0.131
  • S = 0.96
  • 3197 reflections
  • 211 parameters
  • H-atom parameters constrained
  • Δρmax = 0.21 e Å−3
  • Δρmin = −0.26 e Å−3

Data collection: APEX2 and GIS (Bruker, 2009 [triangle]); cell refinement: SAINT (Bruker, 2009 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXTL, OLEX2 (Dolomanov et al., 2009 [triangle]) and FCF_filter (Guzei, 2007 [triangle]); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, modiCIFer (Guzei, 2007 [triangle]) and publCIF (Westrip, 2010 [triangle]).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809054129/zs2023sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809054129/zs2023Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

We thank Dr N. J. Hill (UW-Madison) for acquiring the data and Professor R. West (UW-Madison) for his support. We gratefully acknowledge Bruker sponsorship of this publication and also acknowledge grants NIH 1 S10 RRO 8389–01 and NSF CHE-9629688 for providing NMR spectrometers, and grant NSF CHE-9304546 for providing the mass spectrometer.

supplementary crystallographic information

Comment

Sila phthalimides are important intermediates in photochemistry (Lee et al., 1993, 1996; Yoon et al., 1997, 1992, 1991) and organic synthesis (Bikzhanova et al., 2007; Tsuge et al., 1985). We have used such compounds for the synthesis of selectively substituted sila amines (Bikzhanova et al., 2007) in order to identify biologically active organosilicon compounds. Organosilicon chemistry is a growing method of expanding chemical diversity (Franz, 2007; Franz et al., 2007; Tacke & Zilch, 1986; Showell & Mills, 2003), and it constitutes a powerful method of enhancing pharmacological properties in drug design (Bains & Tacke, 2003). In the course of our studies of silicon-containing anti-cancer compounds the title compound, (I), was synthesized and its structure is reported here.

The bond distances and angles of (I) are typical as confirmed by the Mogul structural check (Bruno et al., 2004), and agree well with those for 2-(3-(methyldiphenylsilyl)propyl)isoindoline-1,3-dione (Guzei, Spencer, Zakai & Lynch, 2010) and 2-(2-(trimethylsilyl)ethyl)isoindoline-1,3-dione (Guzei, Spencer & Zakai, 2010). Specifically, the average Si—C distances of 1.868 (19) Å for compound (I) are statistically similar to the 1.859 (6) Å average for six related compounds in the Cambridge Structural Database (Version 1.11, September 2009 release; Allen, 2002). The Si atom has a distorted tetrahedral geometry with angles ranging from 107.86 (10)° to 110.81 (13)°. Torsion angles C(11/18)-N1-C10-Si1 involving the silyl group are 90.5 (2) and -93.1 (2)°, similar to those in the related compound 6-(phthalimidomethyl(dimethyl)silyl)hexan-1-ol (Latxague & Leger, 2004). This is an indication that there is no interaction between the carbonyl oxygen and the silicon atom despite silicon's high affinity for oxygen (Murai et al., 1998).

The phthalate entity is planar within 0.0084 Å, and the methoxyphenyl group within 0.0044 Å. These groups are nearly parallel forming a 4.61 (8)° angle between their planes. There is one non-classical intermolecular interaction C4–H4···O2 with a C···O distance of 3.410 (3) Å and a C—H ···O angle of 134°. This weak interaction helps link the molecules of (I) into a three-dimensional framework.

Experimental

The protocol described by Tsuge and co-workers (Tsuge et al., 1985) was adopted. The required amount of potassium phthalimide (4.79 g, 25.88 mmol, 1.1 equiv) was placed into a 100 ml round-bottom flask, which was then sealed and flushed with nitrogen three times. Dry DMF (36 ml) was syringed into the flask followed by the addition of 4-methoxybenzylchloride (5.05 g, 23.53 mmol, 1 equiv.) The reaction was heated at 60°C for 6 h and the resulting mixture was then allowed to cool to room temperature. This slurry was poured onto a minimum quantity of water and extracted 3–5 times with ethyl ether. The organic extracts were subsequently collected, dried with magnesium sulfate, and filtered. The filtrate was mixed with silica gel and evaporated under reduced pressure to afford a powder of silica gel. This powder was loaded onto a dry-packed silica gel column and eluted using a gradient column. The fractions of interest were mobilized using a 8:2 hexane:ethyl acetate mixture but did not completely elute until a 1:1 hex:EtOAc mixture was employed. The fractions were then combined to afford the desired compound. Further recrystallization from dichloromethane afforded cream colored crystals (5.35 g, 16.44 mmol, 70% yield) for X-ray crystallography. Manipulation of air and moisture sensitive compounds was performed using standard high-vacuum line techniques. All solvents and reagents were obtained from Aldrich. 4-Methoxybenzylchloride was purchased from Acros Organics. 1H NMR spectra were obtained on a Varian Unity 500 spectrometer, 13C {H} NMR spectra were obtained on a Varian 500 spectrometer operating at 125 MHz, 29Si {H} NMR spectra were obtained on a Varian Unity spectrometer operating at 99 MHz. Mass spectra were determined on a Waters (Micromass) AutoSpec mass spectrometer. Melting points were determined on a Mel-Temp Laboratory Device. mp 75–77°C; 1H NMR (500 MHz, CDCl3) δ 0.36 (s, 6H, CH3), 3.35 (s, 2H, CH2), 3.77 (s, 3H, OMe), 6.87 (m, 2H, ArH), 7.47 (m, 2H, ArH), 7.64 (dd, J=5.45, 3.01 Hz, 2H, ArH), 7.75 (dd, J=5.38, 3.07 Hz, 2H, ArH); 13C NMR (125 MHz, CDCl3) δ -2.9 (SiCH3), 28.8 (CH2), 55.0 (OMe), 113.6 (CH), 122.8 (CH), 127.1 (CH), 132.2 (CH), 133.5 (CH), 135.2 (CH), 160.7 (CH), 168.4 (CH); 29Si NMR (99 MHz, CDCl3) δ -3.17 (SiMe2PhOMe); MS (EI+) m/z (rel. intensity %) 324 (M-1, 9), 310 (M—Me, 100), 218 (56), 165 (75); HRMS (EI+): calcd. for C18H19NO3Si (M+) 325.1129, found (M—Me)+ 310.0894.

Refinement

All H-atoms were placed in idealized locations and refined as riding with appropriate thermal displacement coefficients Uiso(H) = 1.2 or 1.5 times Ueq(bearing atom). The data were collected at room temperature on a Bruker SMART X2S diffractometer in the automated mode and manually processed thereafter.

Figures

Fig. 1.
Molecular structure of (I). The thermal ellipsoids are shown at 50% probability level.

Crystal data

C18H19NO3SiF(000) = 688
Mr = 325.43Dx = 1.275 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 3201 reflections
a = 10.2713 (16) Åθ = 2.3–24.8°
b = 14.061 (3) ŵ = 0.15 mm1
c = 12.069 (2) ÅT = 300 K
β = 103.355 (6)°Block, colourless
V = 1695.9 (5) Å30.50 × 0.40 × 0.23 mm
Z = 4

Data collection

Bruker SMART X2S diffractometer3197 independent reflections
Radiation source: micro-focus sealed tube2338 reflections with I > 2σ(I)
doubly curved silicon crystalRint = 0.042
ω scansθmax = 25.7°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 2009)h = −12→12
Tmin = 0.928, Tmax = 0.966k = −17→17
11394 measured reflectionsl = −11→14

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.046Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.131H-atom parameters constrained
S = 0.96w = 1/[σ2(Fo2) + (0.0812P)2 + 0.1363P] where P = (Fo2 + 2Fc2)/3
3197 reflections(Δ/σ)max < 0.001
211 parametersΔρmax = 0.21 e Å3
0 restraintsΔρmin = −0.26 e Å3

Special details

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)

xyzUiso*/Ueq
Si1−0.00370 (6)0.19378 (4)0.82075 (5)0.0462 (2)
O1−0.34928 (17)0.48107 (11)0.99174 (16)0.0762 (5)
O20.14405 (16)−0.05076 (11)0.93970 (14)0.0674 (5)
O30.38001 (16)0.20812 (11)0.87061 (17)0.0779 (5)
N10.23597 (15)0.09334 (11)0.90879 (13)0.0439 (4)
C1−0.3261 (3)0.57979 (18)0.9894 (3)0.0880 (9)
H1A−0.23640.59351.03070.132*
H1B−0.38840.61271.02400.132*
H1C−0.33770.60040.91190.132*
C2−0.2647 (2)0.42125 (15)0.95212 (18)0.0518 (5)
C3−0.2964 (2)0.32606 (16)0.9526 (2)0.0603 (6)
H3−0.37120.30680.97790.072*
C4−0.2182 (2)0.25971 (15)0.91604 (18)0.0532 (5)
H4−0.24030.19580.91890.064*
C5−0.10617 (18)0.28429 (13)0.87447 (16)0.0426 (5)
C6−0.0790 (2)0.38081 (15)0.87433 (18)0.0521 (5)
H6−0.00600.40070.84700.063*
C7−0.1555 (2)0.44937 (15)0.91292 (19)0.0552 (6)
H7−0.13300.51340.91220.066*
C8−0.1060 (2)0.08665 (17)0.7693 (2)0.0682 (7)
H8A−0.13500.05790.83160.102*
H8B−0.05310.04190.73850.102*
H8C−0.18270.10480.71120.102*
C90.0661 (3)0.2458 (2)0.7055 (2)0.0755 (7)
H9A−0.00490.27300.64840.113*
H9B0.10980.19690.67190.113*
H9C0.12970.29440.73670.113*
C100.1385 (2)0.15592 (15)0.94299 (17)0.0494 (5)
H10A0.18440.21230.97850.059*
H10B0.10140.12350.99960.059*
C110.2303 (2)−0.00539 (14)0.91102 (16)0.0449 (5)
C120.34907 (19)−0.03966 (14)0.87220 (16)0.0466 (5)
C130.3901 (2)−0.13083 (17)0.85585 (19)0.0637 (6)
H130.3418−0.18360.86990.076*
C140.5067 (3)−0.1404 (2)0.8175 (2)0.0792 (8)
H140.5375−0.20090.80550.095*
C150.5775 (3)−0.0621 (2)0.7968 (2)0.0838 (9)
H150.6555−0.07100.77150.101*
C160.5365 (2)0.0289 (2)0.8124 (2)0.0713 (7)
H160.58470.08150.79770.086*
C170.4204 (2)0.03886 (15)0.85097 (17)0.0498 (5)
C180.34950 (19)0.12526 (16)0.87585 (17)0.0515 (5)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Si10.0503 (4)0.0469 (3)0.0444 (3)0.0088 (2)0.0174 (3)0.0027 (2)
O10.0752 (11)0.0601 (10)0.1004 (13)0.0179 (8)0.0350 (10)−0.0101 (9)
O20.0723 (11)0.0521 (9)0.0872 (12)0.0016 (8)0.0377 (9)0.0162 (8)
O30.0658 (11)0.0540 (11)0.1174 (15)−0.0131 (8)0.0284 (10)0.0015 (9)
N10.0430 (9)0.0418 (9)0.0487 (9)0.0035 (7)0.0143 (7)0.0013 (7)
C10.0881 (19)0.0571 (16)0.116 (2)0.0182 (14)0.0166 (17)−0.0252 (15)
C20.0478 (12)0.0503 (12)0.0567 (13)0.0113 (10)0.0112 (10)−0.0017 (10)
C30.0551 (13)0.0580 (14)0.0758 (16)0.0070 (11)0.0316 (12)0.0077 (11)
C40.0581 (13)0.0403 (11)0.0665 (13)0.0034 (10)0.0253 (11)0.0063 (10)
C50.0425 (11)0.0424 (11)0.0420 (10)0.0042 (8)0.0080 (8)0.0054 (8)
C60.0450 (11)0.0482 (12)0.0646 (13)−0.0004 (9)0.0156 (10)0.0031 (10)
C70.0550 (13)0.0365 (11)0.0704 (14)0.0007 (9)0.0069 (11)−0.0012 (10)
C80.0661 (15)0.0660 (15)0.0713 (15)0.0044 (12)0.0136 (12)−0.0197 (12)
C90.0809 (17)0.0925 (19)0.0626 (15)0.0215 (15)0.0363 (13)0.0217 (14)
C100.0564 (12)0.0448 (11)0.0501 (12)0.0086 (9)0.0187 (10)−0.0041 (9)
C110.0504 (12)0.0418 (11)0.0430 (11)0.0051 (9)0.0116 (9)0.0052 (9)
C120.0459 (11)0.0519 (12)0.0389 (11)0.0082 (9)0.0033 (9)−0.0011 (9)
C130.0690 (15)0.0558 (14)0.0628 (14)0.0159 (12)0.0077 (12)−0.0073 (11)
C140.0711 (17)0.085 (2)0.0755 (17)0.0336 (15)0.0050 (14)−0.0252 (15)
C150.0519 (15)0.119 (3)0.0816 (18)0.0232 (17)0.0187 (13)−0.0206 (18)
C160.0421 (12)0.095 (2)0.0787 (17)0.0064 (12)0.0175 (11)−0.0080 (14)
C170.0388 (11)0.0629 (14)0.0456 (11)0.0041 (9)0.0053 (9)−0.0016 (10)
C180.0440 (11)0.0517 (13)0.0569 (13)−0.0012 (10)0.0080 (9)0.0019 (10)

Geometric parameters (Å, °)

Si1—C91.856 (2)C6—H60.9300
Si1—C81.859 (2)C7—H70.9300
Si1—C51.8609 (19)C8—H8A0.9600
Si1—C101.897 (2)C8—H8B0.9600
O1—C21.372 (2)C8—H8C0.9600
O1—C11.410 (3)C9—H9A0.9600
O2—C111.205 (2)C9—H9B0.9600
O3—C181.212 (2)C9—H9C0.9600
N1—C111.390 (3)C10—H10A0.9700
N1—C181.390 (2)C10—H10B0.9700
N1—C101.462 (2)C11—C121.485 (3)
C1—H1A0.9600C12—C131.378 (3)
C1—H1B0.9600C12—C171.381 (3)
C1—H1C0.9600C13—C141.386 (3)
C2—C71.372 (3)C13—H130.9300
C2—C31.378 (3)C14—C151.374 (4)
C3—C41.369 (3)C14—H140.9300
C3—H30.9300C15—C161.373 (4)
C4—C51.400 (3)C15—H150.9300
C4—H40.9300C16—C171.383 (3)
C5—C61.386 (3)C16—H160.9300
C6—C71.390 (3)C17—C181.482 (3)
C9—Si1—C8110.81 (13)H8A—C8—H8C109.5
C9—Si1—C5109.82 (10)H8B—C8—H8C109.5
C8—Si1—C5110.42 (10)Si1—C9—H9A109.5
C9—Si1—C10109.38 (11)Si1—C9—H9B109.5
C8—Si1—C10107.86 (10)H9A—C9—H9B109.5
C5—Si1—C10108.48 (8)Si1—C9—H9C109.5
C2—O1—C1118.2 (2)H9A—C9—H9C109.5
C11—N1—C18111.69 (16)H9B—C9—H9C109.5
C11—N1—C10124.13 (16)N1—C10—Si1113.82 (13)
C18—N1—C10124.10 (17)N1—C10—H10A108.8
O1—C1—H1A109.5Si1—C10—H10A108.8
O1—C1—H1B109.5N1—C10—H10B108.8
H1A—C1—H1B109.5Si1—C10—H10B108.8
O1—C1—H1C109.5H10A—C10—H10B107.7
H1A—C1—H1C109.5O2—C11—N1124.82 (18)
H1B—C1—H1C109.5O2—C11—C12129.12 (19)
O1—C2—C7125.3 (2)N1—C11—C12106.06 (17)
O1—C2—C3115.12 (19)C13—C12—C17121.6 (2)
C7—C2—C3119.63 (19)C13—C12—C11130.4 (2)
C4—C3—C2120.2 (2)C17—C12—C11108.00 (17)
C4—C3—H3119.9C12—C13—C14117.0 (2)
C2—C3—H3119.9C12—C13—H13121.5
C3—C4—C5122.63 (19)C14—C13—H13121.5
C3—C4—H4118.7C15—C14—C13121.1 (2)
C5—C4—H4118.7C15—C14—H14119.4
C6—C5—C4115.11 (18)C13—C14—H14119.4
C6—C5—Si1122.64 (15)C16—C15—C14122.0 (2)
C4—C5—Si1122.24 (15)C16—C15—H15119.0
C5—C6—C7123.3 (2)C14—C15—H15119.0
C5—C6—H6118.3C15—C16—C17117.1 (3)
C7—C6—H6118.3C15—C16—H16121.4
C2—C7—C6119.06 (19)C17—C16—H16121.4
C2—C7—H7120.5C12—C17—C16121.1 (2)
C6—C7—H7120.5C12—C17—C18108.11 (18)
Si1—C8—H8A109.5C16—C17—C18130.8 (2)
Si1—C8—H8B109.5O3—C18—N1124.7 (2)
H8A—C8—H8B109.5O3—C18—C17129.2 (2)
Si1—C8—H8C109.5N1—C18—C17106.09 (18)
C1—O1—C2—C72.1 (3)C18—N1—C11—C12−2.0 (2)
C1—O1—C2—C3−177.5 (2)C10—N1—C11—C12−178.81 (15)
O1—C2—C3—C4−179.3 (2)O2—C11—C12—C131.9 (4)
C7—C2—C3—C41.1 (3)N1—C11—C12—C13−178.2 (2)
C2—C3—C4—C5−1.6 (3)O2—C11—C12—C17−178.8 (2)
C3—C4—C5—C60.8 (3)N1—C11—C12—C171.1 (2)
C3—C4—C5—Si1−178.04 (17)C17—C12—C13—C140.2 (3)
C9—Si1—C5—C6−30.5 (2)C11—C12—C13—C14179.45 (19)
C8—Si1—C5—C6−153.00 (17)C12—C13—C14—C150.0 (4)
C10—Si1—C5—C688.99 (18)C13—C14—C15—C16−0.3 (4)
C9—Si1—C5—C4148.23 (18)C14—C15—C16—C170.4 (4)
C8—Si1—C5—C425.73 (19)C13—C12—C17—C16−0.1 (3)
C10—Si1—C5—C4−92.27 (18)C11—C12—C17—C16−179.46 (18)
C4—C5—C6—C70.4 (3)C13—C12—C17—C18179.50 (18)
Si1—C5—C6—C7179.23 (16)C11—C12—C17—C180.1 (2)
O1—C2—C7—C6−179.48 (19)C15—C16—C17—C12−0.3 (3)
C3—C2—C7—C60.0 (3)C15—C16—C17—C18−179.7 (2)
C5—C6—C7—C2−0.8 (3)C11—N1—C18—O3−177.6 (2)
C11—N1—C10—Si1−93.1 (2)C10—N1—C18—O3−0.8 (3)
C18—N1—C10—Si190.5 (2)C11—N1—C18—C172.1 (2)
C9—Si1—C10—N1−53.22 (18)C10—N1—C18—C17178.88 (16)
C8—Si1—C10—N167.39 (17)C12—C17—C18—O3178.3 (2)
C5—Si1—C10—N1−172.99 (14)C16—C17—C18—O3−2.2 (4)
C18—N1—C11—O2177.87 (19)C12—C17—C18—N1−1.3 (2)
C10—N1—C11—O21.1 (3)C16—C17—C18—N1178.2 (2)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: ZS2023).

References

  • Allen, F. H. (2002). Acta Cryst. B58, 380–388. [PubMed]
  • Bains, W. & Tacke, R. (2003). Curr. Opin. Drug Discov. Devel.6, 526–543. [PubMed]
  • Bikzhanova, G. A., Toulokhonova, I. S., Gately, S. & West, R. (2007). Silicon Chem.3, 209-217.
  • Bruker (2009). APEX2, GIS, SADABS and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Bruno, I. J., Cole, J. C., Kessler, M., Luo, J., Motherwell, W. D. S., Purkis, L. H., Smith, B. R., Taylor, R., Cooper, R. I., Harris, S. E. & Orpen, A. G. (2004). J. Chem. Inf. Comput. Sci.44, 2133–2144. [PubMed]
  • Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst.42, 339–341.
  • Franz, A. K. T. (2007). Curr. Opin. Drug Discov. Devel.10, 654–671. [PubMed]
  • Franz, A. K., Dreyfuss, P. D. & Schreiber, S. L. (2007). J. Am. Chem. Soc.129, 1020–1021. [PubMed]
  • Gately, S. & West, R. (2007). Drug Dev. Res.68, 156–163.
  • Guzei, I. A. (2007). In-house Crystallographic Programs: FCF_filter, INSerter and modiCIFer Molecular Structure Laboratory, University of Wisconsin–Madison, Madison, Wisconsin, USA.
  • Guzei, I. A., Spencer, L. C. & Zakai, U. I. (2010). Acta Cryst. E66, o223–o224. [PMC free article] [PubMed]
  • Guzei, I. A., Spencer, L. C., Zakai, U. I. & Lynch, D. C. (2010). Acta Cryst. E66, o221–o222. [PMC free article] [PubMed]
  • Latxague, L. & Leger, J.-M. (2004). Anal. Sci.20, x125–x126.
  • Lee, Y. J., Lee, C. P., Jeon, Y. T., Mariano, P. S., Yoon, U. C., Kim, D. U., Kim, J. C. & Lee, J. G. (1993). Tetrahedron Lett.34, 5855–5858.
  • Lee, Y. J., Ling, R., Mariano, P. S., Yoon, U. C., Kim, D. U. & Oh, S. W. (1996). J. Org. Chem.61, 3304–3314.
  • Murai, T., Kimura, F., Tsutsui, K., Hasegawa, K. & Kato, S. (1998). Organometallics, 17, 926–932.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Showell, G. A. & Mills, J. S. (2003). Drug Discov. Today, 8, 551–556. [PubMed]
  • Tacke, R. & Zilch, H. (1986). Endeavour, 10, 191–197. [PubMed]
  • Tsuge, O., Tanaka, J. & Kanemasa, S. (1985). Bull. Chem. Soc. Jpn, 58, 1991–1999.
  • Westrip, S. P. (2010). publCIF. In preparation.
  • Yoon, U. C., Cho, S. J., Oh, J. H., Lee, J. G., Kang, K. T. & Mariano, P. S. (1991). Bull. Korean Chem. Soc.12, 241–243.
  • Yoon, U. C., Kim, J. W., Ryu, J. Y., Cho, S. J., Oh, S. W. & Mariano, P. S. (1997). J. Photochem. Photobiol. A Chem.106, 145–154.
  • Yoon, U. C., Oh, J. H., Lee, S. J., Kim, D. U., Lee, J. G., Kang, K. T. & Mariano, P. S. (1992). Bull. Korean Chem. Soc.13, 166–172.

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography