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

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ISSN: 2056-9890

1-[2-(Trit­yl­oxy)phen­yl]ethanone

aDepartment of Basic Science, Tianjin Agricultural University, Tianjin 300384, People's Republic of China
*Correspondence e-mail: zhaopengying@eyou.com

(Received 18 February 2013; accepted 12 May 2013; online 18 May 2013)

In the title compound, C27H22O2, the acetyl group is nearly coplanar with the the ring to which it attacted [O—C—C—C torsion angle = −5.5 (3)°]. The three phenyl groups of the tri­phenyl­methyl substituent are mutually nearly perpendicular, making dihedral angles of 89.87 (11) and 78.29 (11) and 60.34 (11)°. Two intra­molecular C—H⋯ O hydrogen bonds occur. In the crystal, C—H⋯ O hydrogen bonds link the moleclues into chains along the b-axis direction.

Related literature

For general background to tri­phenyl­methyl, see: Casanova et al. (2006[Casanova, E., Hernandez, A.-I., Priego, E.-M., Liekens, S., Camarasa, M.-J., Balzarini, J. & Perez-Perez, M.-J. (2006). J. Med. Chem. 49, 5562-5570.]); Aldaye & Sleiman (2007[Aldaye, F. A. & Sleiman, H. F. (2007). J. Am. Chem. Soc. 129, 10070-10071.]).

[Scheme 1]

Experimental

Crystal data
  • C27H22O2

  • Mr = 378.45

  • Orthorhombic, P b c a

  • a = 15.6996 (17) Å

  • b = 8.8767 (9) Å

  • c = 29.591 (3) Å

  • V = 4123.8 (7) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 0.08 mm−1

  • T = 296 K

  • 0.26 × 0.24 × 0.20 mm

Data collection
  • Bruker SMART CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 1996[Bruker (1996). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.674, Tmax = 0.745

  • 21669 measured reflections

  • 3653 independent reflections

  • 2496 reflections with I > 2σ(I)

  • Rint = 0.053

Refinement
  • R[F2 > 2σ(F2)] = 0.045

  • wR(F2) = 0.128

  • S = 1.02

  • 3653 reflections

  • 263 parameters

  • H-atom parameters constrained

  • Δρmax = 0.13 e Å−3

  • Δρmin = −0.16 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C14—H14⋯O1i 0.93 2.56 3.444 (3) 158
C21—H21⋯O2 0.93 2.46 2.810 (3) 103
C5—H5⋯O1 0.93 2.36 2.701 (3) 101
Symmetry code: (i) [-x+2, y-{\script{1\over 2}}, -z+{\script{3\over 2}}].

Data collection: SMART (Bruker, 2007[Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; 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: DIAMOND (Brandenburg, 1999[Brandenburg, K. (1999). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]).

Supporting information


Comment top

Trityloxy aromatic ketones are useful intermediates in organic synthesis (Casanova et al. 2006). The X-ray analysis of the title compound C27H22O2 (Fig. 1) is shown in Fig. 1. The ethanoyl group is nearly coplanar with the the ring to which it attacted, reflected by the O1—C7—C6—C5 torsion angle of -5.4 (3)°. Phenyl ring (C10—C15) makes dihedral angles of 89.87 (11) and 78.29 (11)° with the phenyl rings (C16—C21) and (C22—C27). The intermolecular hydrogen bonds C14—H14···O1 and C21—H21···O2 link adjacent moleclues, forming an infinite one-dimensional chain along the b axis. Furthermore, each molecule of the asymmetric unit exhibits an intramolecular C5—H5···O1 hydrogen bond.

Related literature top

For general background to triphenylmethyl, see: Casanova et al. (2006); Aldaye et al. (2007).

Experimental top

A 50 ml flask, fitted with a condenser, was charged with o-hydroxyacetophenone (3.00 g, 22.03 mmol), trityl chloride (5.84 g, 20.95 mmol), dry CH2Cl2 (20 ml), triethylamine (3.1 ml, 22.24 mmol) and 4-dimethylaminopyridine (270 mg). The reaction was refluxed for 96 h under nitrogen. After cooling to room temperature, the reaction mixture was washed three times with 10% aqueous NaOH, dried with anhydrous K2CO3. The crude material was purified by column chromatography(5% anhydrous Na2CO3 in silica gel, hexane:ethyl acetate: NEt3= 100:10:1 as eluent) to provide 6.58 g of o-trityloxyacetophenone as a white solid (83% yield). Crystallization from EtOH (containing 1% NEt3) afforded the single-crystal.

Refinement top

H atoms bonded to C were positioned with idealized geometry using a riding model with the aromatic C—H = 0.93 Å, methyl C—H = 0.96 Å. All H atoms were refined with isotropic displacement parameters set at 1.2 Ueq(C-aromati) and 1.5 Ueq (C-methyl) of the parent atom.

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 1999); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. A view of the molecular structure of the title compound with the intramolecular hydrogen bond. The displacement ellipsoids are drawn at the 30% probability level.
[Figure 2] Fig. 2. A view of the hydrogen bonded polymeric chain. The hydrogen bonds are shown as dashed lines.
1-[2-(Trityloxy)phenyl]ethanone top
Crystal data top
C27H22O2F(000) = 1600
Mr = 378.45Dx = 1.219 Mg m3
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 3063 reflections
a = 15.6996 (17) Åθ = 2.6–21.8°
b = 8.8767 (9) ŵ = 0.08 mm1
c = 29.591 (3) ÅT = 296 K
V = 4123.8 (7) Å3Block, colourless
Z = 80.26 × 0.24 × 0.20 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer
3653 independent reflections
Radiation source: fine-focus sealed tube2496 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.053
phi and ω scansθmax = 25.0°, θmin = 1.4°
Absorption correction: multi-scan
(SADABS; Bruker, 1996)
h = 1815
Tmin = 0.674, Tmax = 0.745k = 1010
21669 measured reflectionsl = 3528
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)] = 0.045Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.128H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.0619P)2 + 0.751P]
where P = (Fo2 + 2Fc2)/3
3653 reflections(Δ/σ)max = 0.001
263 parametersΔρmax = 0.13 e Å3
0 restraintsΔρmin = 0.16 e Å3
Crystal data top
C27H22O2V = 4123.8 (7) Å3
Mr = 378.45Z = 8
Orthorhombic, PbcaMo Kα radiation
a = 15.6996 (17) ŵ = 0.08 mm1
b = 8.8767 (9) ÅT = 296 K
c = 29.591 (3) Å0.26 × 0.24 × 0.20 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer
3653 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 1996)
2496 reflections with I > 2σ(I)
Tmin = 0.674, Tmax = 0.745Rint = 0.053
21669 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0450 restraints
wR(F2) = 0.128H-atom parameters constrained
S = 1.02Δρmax = 0.13 e Å3
3653 reflectionsΔρmin = 0.16 e Å3
263 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
O10.83938 (14)0.9201 (2)0.78288 (6)0.0885 (6)
O20.97143 (9)0.99213 (14)0.66452 (4)0.0430 (4)
C10.93023 (12)1.1103 (2)0.68509 (6)0.0418 (5)
C20.93469 (14)1.2572 (2)0.66877 (7)0.0518 (6)
H20.96461.27740.64230.062*
C30.89509 (16)1.3726 (3)0.69158 (8)0.0652 (7)
H30.89791.47030.68030.078*
C40.85108 (17)1.3441 (3)0.73112 (9)0.0724 (8)
H40.82481.42220.74670.087*
C50.84667 (15)1.1997 (3)0.74704 (8)0.0626 (7)
H50.81641.18120.77350.075*
C60.88591 (13)1.0789 (2)0.72507 (6)0.0456 (5)
C70.87505 (15)0.9273 (3)0.74669 (7)0.0537 (6)
C80.9036 (2)0.7862 (3)0.72541 (9)0.0893 (10)
H8A0.88500.70210.74320.134*
H8B0.96470.78570.72350.134*
H8C0.87990.77880.69560.134*
C90.98726 (12)0.9888 (2)0.61572 (6)0.0372 (5)
C161.07153 (12)1.0672 (2)0.60443 (6)0.0371 (4)
C211.11903 (13)1.1444 (2)0.63622 (7)0.0488 (5)
H211.09941.15110.66580.059*
C201.19551 (14)1.2119 (3)0.62452 (8)0.0605 (6)
H201.22611.26540.64610.073*
C191.22651 (15)1.2004 (3)0.58119 (8)0.0604 (6)
H191.27771.24620.57340.073*
C181.18105 (15)1.1206 (3)0.54957 (8)0.0556 (6)
H181.20201.11120.52030.067*
C171.10481 (13)1.0543 (2)0.56092 (7)0.0462 (5)
H171.07491.00010.53920.055*
C220.90861 (12)1.0482 (2)0.59090 (6)0.0396 (5)
C230.91211 (14)1.1540 (2)0.55649 (7)0.0481 (5)
H230.96441.19390.54780.058*
C240.83844 (16)1.2008 (3)0.53496 (8)0.0608 (6)
H240.84171.27120.51180.073*
C250.76079 (16)1.1442 (3)0.54752 (8)0.0662 (7)
H250.71161.17610.53290.079*
C260.75589 (15)1.0406 (3)0.58172 (8)0.0605 (6)
H260.70321.00270.59060.073*
C270.82935 (14)0.9922 (2)0.60313 (7)0.0514 (5)
H270.82550.92090.62610.062*
C101.00059 (12)0.8202 (2)0.60568 (6)0.0373 (5)
C110.96804 (14)0.7533 (2)0.56714 (7)0.0488 (5)
H110.93310.80820.54790.059*
C120.98735 (15)0.6048 (2)0.55720 (8)0.0612 (6)
H120.96490.56040.53130.073*
C131.03894 (16)0.5228 (2)0.58499 (8)0.0610 (6)
H131.05200.42340.57790.073*
C141.07137 (16)0.5871 (2)0.62336 (8)0.0586 (6)
H141.10600.53110.64250.070*
C151.05261 (14)0.7353 (2)0.63351 (7)0.0487 (5)
H151.07530.77860.65950.058*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.1163 (16)0.1011 (14)0.0480 (10)0.0199 (12)0.0248 (10)0.0035 (9)
O20.0546 (9)0.0418 (7)0.0326 (7)0.0061 (7)0.0067 (6)0.0006 (6)
C10.0427 (11)0.0451 (12)0.0376 (11)0.0000 (9)0.0046 (9)0.0088 (9)
C20.0614 (15)0.0440 (12)0.0498 (13)0.0001 (11)0.0126 (11)0.0050 (10)
C30.0753 (17)0.0466 (13)0.0737 (17)0.0049 (12)0.0114 (14)0.0114 (12)
C40.0726 (18)0.0660 (18)0.0786 (18)0.0063 (14)0.0219 (14)0.0260 (14)
C50.0603 (15)0.0739 (17)0.0536 (14)0.0059 (13)0.0174 (12)0.0186 (13)
C60.0415 (12)0.0563 (13)0.0389 (11)0.0042 (10)0.0022 (9)0.0078 (10)
C70.0524 (13)0.0711 (15)0.0378 (12)0.0140 (12)0.0019 (10)0.0015 (11)
C80.132 (3)0.0568 (16)0.0792 (19)0.0034 (17)0.0404 (18)0.0150 (14)
C90.0459 (12)0.0379 (10)0.0278 (10)0.0026 (9)0.0039 (8)0.0004 (8)
C160.0413 (11)0.0351 (10)0.0348 (10)0.0042 (9)0.0012 (9)0.0005 (8)
C210.0468 (12)0.0596 (13)0.0400 (11)0.0002 (10)0.0012 (10)0.0072 (10)
C200.0467 (14)0.0689 (16)0.0659 (16)0.0072 (11)0.0061 (12)0.0107 (12)
C190.0463 (13)0.0641 (15)0.0709 (17)0.0071 (11)0.0085 (12)0.0025 (13)
C180.0578 (14)0.0603 (14)0.0488 (13)0.0042 (12)0.0143 (11)0.0048 (11)
C170.0541 (13)0.0460 (12)0.0386 (11)0.0025 (10)0.0040 (10)0.0021 (9)
C220.0447 (12)0.0359 (10)0.0381 (11)0.0047 (9)0.0006 (9)0.0042 (8)
C230.0542 (13)0.0427 (12)0.0474 (12)0.0051 (10)0.0029 (10)0.0002 (10)
C240.0679 (17)0.0546 (14)0.0599 (15)0.0125 (12)0.0114 (12)0.0077 (11)
C250.0555 (15)0.0696 (16)0.0734 (17)0.0196 (13)0.0160 (13)0.0010 (14)
C260.0426 (13)0.0661 (16)0.0730 (16)0.0032 (11)0.0019 (12)0.0067 (13)
C270.0497 (13)0.0503 (12)0.0543 (13)0.0022 (10)0.0039 (11)0.0006 (10)
C100.0396 (11)0.0353 (10)0.0369 (11)0.0006 (9)0.0058 (9)0.0003 (8)
C110.0516 (13)0.0473 (12)0.0475 (12)0.0041 (10)0.0032 (10)0.0068 (10)
C120.0666 (16)0.0508 (13)0.0662 (15)0.0003 (12)0.0013 (12)0.0208 (12)
C130.0672 (16)0.0377 (12)0.0781 (17)0.0027 (11)0.0141 (13)0.0065 (12)
C140.0682 (16)0.0435 (13)0.0642 (15)0.0125 (11)0.0062 (12)0.0096 (11)
C150.0546 (13)0.0480 (12)0.0436 (12)0.0054 (10)0.0005 (10)0.0018 (10)
Geometric parameters (Å, º) top
O1—C71.210 (2)C19—C181.374 (3)
O2—C11.374 (2)C19—H190.9300
O2—C91.466 (2)C18—C171.375 (3)
C1—C21.393 (3)C18—H180.9300
C1—C61.401 (3)C17—H170.9300
C2—C31.375 (3)C22—C231.386 (3)
C2—H20.9300C22—C271.388 (3)
C3—C41.382 (3)C23—C241.384 (3)
C3—H30.9300C23—H230.9300
C4—C51.367 (3)C24—C251.370 (3)
C4—H40.9300C24—H240.9300
C5—C61.397 (3)C25—C261.370 (3)
C5—H50.9300C25—H250.9300
C6—C71.500 (3)C26—C271.384 (3)
C7—C81.472 (3)C26—H260.9300
C8—H8A0.9600C27—H270.9300
C8—H8B0.9600C10—C151.383 (3)
C8—H8C0.9600C10—C111.384 (3)
C9—C221.530 (3)C11—C121.384 (3)
C9—C161.532 (3)C11—H110.9300
C9—C101.540 (3)C12—C131.364 (3)
C16—C211.382 (3)C12—H120.9300
C16—C171.394 (3)C13—C141.369 (3)
C21—C201.386 (3)C13—H130.9300
C21—H210.9300C14—C151.381 (3)
C20—C191.375 (3)C14—H140.9300
C20—H200.9300C15—H150.9300
C1—O2—C9122.10 (14)C18—C19—H19120.4
O2—C1—C2122.52 (17)C20—C19—H19120.4
O2—C1—C6117.15 (17)C19—C18—C17120.4 (2)
C2—C1—C6120.27 (18)C19—C18—H18119.8
C3—C2—C1120.3 (2)C17—C18—H18119.8
C3—C2—H2119.8C18—C17—C16121.1 (2)
C1—C2—H2119.8C18—C17—H17119.4
C2—C3—C4120.3 (2)C16—C17—H17119.4
C2—C3—H3119.8C23—C22—C27118.02 (19)
C4—C3—H3119.8C23—C22—C9123.64 (18)
C5—C4—C3119.3 (2)C27—C22—C9118.34 (17)
C5—C4—H4120.4C24—C23—C22120.5 (2)
C3—C4—H4120.4C24—C23—H23119.7
C4—C5—C6122.4 (2)C22—C23—H23119.7
C4—C5—H5118.8C25—C24—C23120.6 (2)
C6—C5—H5118.8C25—C24—H24119.7
C5—C6—C1117.4 (2)C23—C24—H24119.7
C5—C6—C7116.10 (19)C24—C25—C26119.8 (2)
C1—C6—C7126.52 (19)C24—C25—H25120.1
O1—C7—C8118.4 (2)C26—C25—H25120.1
O1—C7—C6118.5 (2)C25—C26—C27120.0 (2)
C8—C7—C6123.11 (19)C25—C26—H26120.0
C7—C8—H8A109.5C27—C26—H26120.0
C7—C8—H8B109.5C26—C27—C22121.1 (2)
H8A—C8—H8B109.5C26—C27—H27119.5
C7—C8—H8C109.5C22—C27—H27119.5
H8A—C8—H8C109.5C15—C10—C11118.31 (18)
H8B—C8—H8C109.5C15—C10—C9119.69 (17)
O2—C9—C22109.22 (15)C11—C10—C9121.75 (17)
O2—C9—C16110.62 (15)C10—C11—C12120.2 (2)
C22—C9—C16115.84 (15)C10—C11—H11119.9
O2—C9—C10103.44 (14)C12—C11—H11119.9
C22—C9—C10110.60 (15)C13—C12—C11120.6 (2)
C16—C9—C10106.39 (14)C13—C12—H12119.7
C21—C16—C17117.84 (19)C11—C12—H12119.7
C21—C16—C9122.88 (17)C12—C13—C14119.9 (2)
C17—C16—C9119.20 (17)C12—C13—H13120.1
C16—C21—C20120.78 (19)C14—C13—H13120.1
C16—C21—H21119.6C13—C14—C15119.9 (2)
C20—C21—H21119.6C13—C14—H14120.1
C19—C20—C21120.5 (2)C15—C14—H14120.1
C19—C20—H20119.7C14—C15—C10121.0 (2)
C21—C20—H20119.7C14—C15—H15119.5
C18—C19—C20119.3 (2)C10—C15—H15119.5
C9—O2—C1—C230.2 (3)C19—C18—C17—C160.4 (3)
C9—O2—C1—C6152.75 (17)C21—C16—C17—C182.1 (3)
O2—C1—C2—C3177.4 (2)C9—C16—C17—C18178.78 (18)
C6—C1—C2—C30.5 (3)O2—C9—C22—C23132.84 (18)
C1—C2—C3—C40.5 (4)C16—C9—C22—C237.2 (3)
C2—C3—C4—C50.6 (4)C10—C9—C22—C23114.0 (2)
C3—C4—C5—C60.7 (4)O2—C9—C22—C2747.8 (2)
C4—C5—C6—C10.6 (4)C16—C9—C22—C27173.50 (17)
C4—C5—C6—C7179.9 (2)C10—C9—C22—C2765.4 (2)
O2—C1—C6—C5177.59 (18)C27—C22—C23—C240.5 (3)
C2—C1—C6—C50.5 (3)C9—C22—C23—C24178.87 (18)
O2—C1—C6—C73.3 (3)C22—C23—C24—C250.5 (3)
C2—C1—C6—C7179.6 (2)C23—C24—C25—C260.1 (4)
C5—C6—C7—O15.5 (3)C24—C25—C26—C270.7 (4)
C1—C6—C7—O1175.4 (2)C25—C26—C27—C220.7 (3)
C5—C6—C7—C8172.8 (2)C23—C22—C27—C260.1 (3)
C1—C6—C7—C86.4 (4)C9—C22—C27—C26179.52 (18)
C1—O2—C9—C2240.9 (2)O2—C9—C10—C1545.7 (2)
C1—O2—C9—C1687.8 (2)C22—C9—C10—C15162.49 (17)
C1—O2—C9—C10158.66 (16)C16—C9—C10—C1570.9 (2)
O2—C9—C16—C217.0 (2)O2—C9—C10—C11140.23 (18)
C22—C9—C16—C21118.0 (2)C22—C9—C10—C1123.4 (2)
C10—C9—C16—C21118.67 (19)C16—C9—C10—C11103.2 (2)
O2—C9—C16—C17169.50 (16)C15—C10—C11—C120.2 (3)
C22—C9—C16—C1765.5 (2)C9—C10—C11—C12174.41 (19)
C10—C9—C16—C1757.8 (2)C10—C11—C12—C130.4 (3)
C17—C16—C21—C202.6 (3)C11—C12—C13—C140.7 (4)
C9—C16—C21—C20179.15 (19)C12—C13—C14—C150.8 (4)
C16—C21—C20—C191.4 (3)C13—C14—C15—C100.6 (3)
C21—C20—C19—C180.3 (4)C11—C10—C15—C140.4 (3)
C20—C19—C18—C170.8 (4)C9—C10—C15—C14174.67 (19)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C14—H14···O1i0.932.563.444 (3)158
C21—H21···O20.932.462.810 (3)103
C5—H5···O10.932.362.701 (3)101
Symmetry code: (i) x+2, y1/2, z+3/2.

Experimental details

Crystal data
Chemical formulaC27H22O2
Mr378.45
Crystal system, space groupOrthorhombic, Pbca
Temperature (K)296
a, b, c (Å)15.6996 (17), 8.8767 (9), 29.591 (3)
V3)4123.8 (7)
Z8
Radiation typeMo Kα
µ (mm1)0.08
Crystal size (mm)0.26 × 0.24 × 0.20
Data collection
DiffractometerBruker SMART CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 1996)
Tmin, Tmax0.674, 0.745
No. of measured, independent and
observed [I > 2σ(I)] reflections
21669, 3653, 2496
Rint0.053
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.045, 0.128, 1.02
No. of reflections3653
No. of parameters263
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.13, 0.16

Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg, 1999), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C14—H14···O1i0.932.563.444 (3)157.9
C21—H21···O20.932.462.810 (3)102.7
C5—H5···O10.932.362.701 (3)101.2
Symmetry code: (i) x+2, y1/2, z+3/2.
 

References

First citationAldaye, F. A. & Sleiman, H. F. (2007). J. Am. Chem. Soc. 129, 10070–10071.  Web of Science CrossRef PubMed CAS
First citationBrandenburg, K. (1999). DIAMOND. Crystal Impact GbR, Bonn, Germany.
First citationBruker (1996). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
First citationBruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
First citationCasanova, E., Hernandez, A.-I., Priego, E.-M., Liekens, S., Camarasa, M.-J., Balzarini, J. & Perez-Perez, M.-J. (2006). J. Med. Chem. 49, 5562–5570.  Web of Science CrossRef PubMed CAS
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals

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