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Acta Crystallogr Sect E Struct Rep Online. 2010 October 1; 66(Pt 10): o2681.
Published online 2010 September 30. doi:  10.1107/S1600536810038602
PMCID: PMC2983158

tert-Butyl 4-cyano­phenyl carbonate

Abstract

The title compound, C12H13NO3, was prepared by reacting one equivalent of di-tert-butyl dicarbonate with 4-cyano­phenol. Herringbone crystal packing is observed and there are no significant inter­molecular inter­actions.

Related literature

For a similar packing arrangement in related structures, see: Girard et al. (2005 [triangle]); Nagata et al. (2008 [triangle]). For reference structural data, see: Allen et al. (1987 [triangle]).

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Object name is e-66-o2681-scheme1.jpg

Experimental

Crystal data

  • C12H13NO3
  • M r = 219.23
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-o2681-efi1.jpg
  • a = 5.7347 (7) Å
  • b = 14.3237 (16) Å
  • c = 13.7727 (16) Å
  • β = 101.110 (1)°
  • V = 1110.1 (2) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.10 mm−1
  • T = 296 K
  • 0.45 × 0.25 × 0.12 mm

Data collection

  • Bruker APEX CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2009 [triangle]) T min = 0.959, T max = 0.989
  • 6536 measured reflections
  • 2427 independent reflections
  • 2100 reflections with I > 2σ(I)
  • R int = 0.017

Refinement

  • R[F 2 > 2σ(F 2)] = 0.034
  • wR(F 2) = 0.091
  • S = 1.05
  • 2427 reflections
  • 148 parameters
  • H-atom parameters constrained
  • Δρmax = 0.31 e Å−3
  • Δρmin = −0.23 e Å−3

Data collection: APEX2 (Bruker, 2009 [triangle]); cell refinement: SAINT (Bruker, 2009 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: X-SEED (Barbour, 2001 [triangle]; Atwood & Barbour, 2003 [triangle]); software used to prepare material for publication: X-SEED (Barbour, 2001 [triangle]; Atwood & Barbour, 2003 [triangle]).

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810038602/bh2315sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810038602/bh2315Isup2.hkl

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

Acknowledgments

The author would like to thank the Central Analytical Facility (CAF) at the University of Stellenbosch (US) for the use of their diffractometer as well as the US and the NRF for funding.

supplementary crystallographic information

Comment

In the title molecule, all bond lengths after refinement are within the normal values as previously collected by Allen et al. (1987).

The two-dimensional herring-bone type packing along the b and c axis observed has two molecules oriented in opposite directions in each turn. Such an arrangement is similar to that described by Girard et al. (2005) and Nagata et al. (2008) for related organics.

Experimental

Di-tert-butyl dicarbonate (279 mg, 1.28 mmol) was added to 4-cyano phenol in 5 ml of dichloromethane. 4-Dimethylamino pyridine (5.20 mg, 0.043 mmol) as a catalyst and triethylamine (0.263 ml, 1.87 mmol) as a base were also added. The solution was stirred at room temperature for six hours.

The reaction was then worked-up using 20 ml of H2O and 10 ml of 2M HCl which was repeated. The solution was then dried over MgSO4 after which the solvent was reduced. The resultant white solid was then dried thoroughly under vacuum.

Refinement

Structure solution and refinement were performed using the SHELX97 suite of programs (Sheldrick, 2008). The H atoms were placed in calculated positions, using and refined using a riding model, with C—H bond lengths fixed to 0.93 (aromatic CH) or 0.96 Å (methyl CH3).

Figures

Fig. 1.
The molecular structure of the title compound showing the 50% probability ellipsoids for non-H atoms.
Fig. 2.
The crystal packing viewed down the a axis which shows the herring-bone type packing and the two oppositely oriented molecules in each turn.

Crystal data

C12H13NO3F(000) = 464
Mr = 219.23Dx = 1.312 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 3143 reflections
a = 5.7347 (7) Åθ = 2.8–27.5°
b = 14.3237 (16) ŵ = 0.10 mm1
c = 13.7727 (16) ÅT = 296 K
β = 101.110 (1)°Plate, colourless
V = 1110.1 (2) Å30.45 × 0.25 × 0.12 mm
Z = 4

Data collection

Bruker APEX CCD area-detector diffractometer2427 independent reflections
Radiation source: fine-focus sealed tube2100 reflections with I > 2σ(I)
graphiteRint = 0.017
ω scansθmax = 27.9°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2009)h = −7→7
Tmin = 0.959, Tmax = 0.989k = −18→14
6536 measured reflectionsl = −17→15

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)] = 0.034Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.091H-atom parameters constrained
S = 1.05w = 1/[σ2(Fo2) + (0.0448P)2 + 0.3462P] where P = (Fo2 + 2Fc2)/3
2427 reflections(Δ/σ)max < 0.001
148 parametersΔρmax = 0.31 e Å3
0 restraintsΔρmin = −0.23 e Å3
0 constraints

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
N10.33241 (18)0.70351 (7)0.16270 (7)0.0241 (2)
C20.4174 (2)0.69212 (8)0.24446 (8)0.0182 (2)
C30.52163 (19)0.67936 (8)0.34783 (8)0.0163 (2)
C40.74719 (19)0.71664 (8)0.38553 (8)0.0180 (2)
H40.83220.74690.34380.022*
C50.84213 (19)0.70792 (8)0.48552 (8)0.0187 (2)
H50.99110.73250.51170.022*
C60.7118 (2)0.66212 (8)0.54586 (8)0.0170 (2)
C70.4902 (2)0.62391 (8)0.50998 (8)0.0187 (2)
H70.40720.59310.55210.022*
C80.3944 (2)0.63258 (8)0.40994 (8)0.0182 (2)
H80.24590.60730.38430.022*
O90.79952 (14)0.65945 (6)0.64836 (6)0.0199 (2)
C100.97513 (19)0.59643 (8)0.68019 (8)0.0159 (2)
O111.04663 (14)0.53999 (6)0.62887 (6)0.0211 (2)
O121.04148 (14)0.61088 (6)0.77662 (5)0.01731 (19)
C131.22277 (19)0.54939 (8)0.83729 (8)0.0161 (2)
C141.2463 (2)0.59433 (9)0.93865 (8)0.0210 (3)
H14A1.30210.65730.93590.032*
H14B1.35750.55940.98600.032*
H14C1.09430.59470.95810.032*
C151.1255 (2)0.45053 (8)0.83660 (9)0.0203 (2)
H15A0.97510.45160.85740.030*
H15B1.23500.41230.88110.030*
H15C1.10500.42540.77090.030*
C161.45548 (19)0.55369 (8)0.79966 (8)0.0189 (2)
H16A1.43850.52040.73820.028*
H16B1.57980.52570.84750.028*
H16C1.49480.61770.78960.028*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
N10.0254 (5)0.0257 (6)0.0193 (5)−0.0037 (4)−0.0003 (4)0.0010 (4)
C20.0180 (5)0.0158 (5)0.0206 (6)−0.0013 (4)0.0029 (4)−0.0008 (4)
C30.0179 (5)0.0151 (5)0.0150 (5)0.0023 (4)0.0012 (4)−0.0004 (4)
C40.0181 (5)0.0186 (5)0.0176 (5)−0.0002 (4)0.0039 (4)0.0022 (4)
C50.0150 (5)0.0210 (6)0.0189 (6)−0.0004 (4)0.0007 (4)0.0001 (4)
C60.0187 (5)0.0184 (5)0.0135 (5)0.0058 (4)0.0019 (4)0.0013 (4)
C70.0201 (5)0.0181 (6)0.0191 (6)0.0015 (4)0.0070 (4)0.0025 (4)
C80.0158 (5)0.0175 (5)0.0207 (6)−0.0009 (4)0.0022 (4)−0.0012 (4)
O90.0201 (4)0.0259 (4)0.0133 (4)0.0071 (3)0.0020 (3)0.0025 (3)
C100.0144 (5)0.0171 (5)0.0160 (5)−0.0008 (4)0.0029 (4)0.0025 (4)
O110.0240 (4)0.0221 (4)0.0167 (4)0.0043 (3)0.0026 (3)−0.0016 (3)
O120.0181 (4)0.0204 (4)0.0130 (4)0.0056 (3)0.0018 (3)0.0013 (3)
C130.0153 (5)0.0179 (5)0.0144 (5)0.0036 (4)0.0008 (4)0.0032 (4)
C140.0238 (6)0.0241 (6)0.0144 (5)0.0055 (5)0.0016 (4)0.0012 (4)
C150.0192 (5)0.0197 (6)0.0221 (6)0.0001 (4)0.0040 (4)0.0035 (4)
C160.0168 (5)0.0191 (6)0.0208 (6)0.0010 (4)0.0037 (4)0.0014 (4)

Geometric parameters (Å, °)

N1—C21.1493 (15)C10—O121.3254 (13)
C2—C31.4455 (15)O12—C131.4899 (13)
C3—C81.3979 (16)C13—C141.5194 (15)
C3—C41.4032 (15)C13—C151.5214 (16)
C4—C51.3855 (15)C13—C161.5231 (15)
C4—H40.9300C14—H14A0.9600
C5—C61.3850 (16)C14—H14B0.9600
C5—H50.9300C14—H14C0.9600
C6—C71.3846 (16)C15—H15A0.9600
C6—O91.4049 (13)C15—H15B0.9600
C7—C81.3871 (16)C15—H15C0.9600
C7—H70.9300C16—H16A0.9600
C8—H80.9300C16—H16B0.9600
O9—C101.3605 (13)C16—H16C0.9600
C10—O111.1971 (14)
N1—C2—C3178.86 (13)O12—C13—C14101.18 (8)
C8—C3—C4120.57 (10)O12—C13—C15109.34 (9)
C8—C3—C2119.85 (10)C14—C13—C15111.57 (9)
C4—C3—C2119.55 (10)O12—C13—C16110.35 (9)
C5—C4—C3119.42 (10)C14—C13—C16111.52 (9)
C5—C4—H4120.3C15—C13—C16112.32 (9)
C3—C4—H4120.3C13—C14—H14A109.5
C6—C5—C4119.01 (10)C13—C14—H14B109.5
C6—C5—H5120.5H14A—C14—H14B109.5
C4—C5—H5120.5C13—C14—H14C109.5
C7—C6—C5122.50 (10)H14A—C14—H14C109.5
C7—C6—O9118.29 (10)H14B—C14—H14C109.5
C5—C6—O9119.07 (10)C13—C15—H15A109.5
C6—C7—C8118.67 (10)C13—C15—H15B109.5
C6—C7—H7120.7H15A—C15—H15B109.5
C8—C7—H7120.7C13—C15—H15C109.5
C7—C8—C3119.82 (10)H15A—C15—H15C109.5
C7—C8—H8120.1H15B—C15—H15C109.5
C3—C8—H8120.1C13—C16—H16A109.5
C10—O9—C6116.18 (9)C13—C16—H16B109.5
O11—C10—O12129.21 (10)H16A—C16—H16B109.5
O11—C10—O9125.05 (10)C13—C16—H16C109.5
O12—C10—O9105.73 (9)H16A—C16—H16C109.5
C10—O12—C13120.28 (8)H16B—C16—H16C109.5
C8—C3—C4—C5−0.93 (17)C7—C6—O9—C10105.80 (12)
C2—C3—C4—C5177.14 (10)C5—C6—O9—C10−78.37 (13)
C3—C4—C5—C60.27 (17)C6—O9—C10—O11−5.43 (16)
C4—C5—C6—C70.48 (17)C6—O9—C10—O12175.49 (9)
C4—C5—C6—O9−175.16 (10)O11—C10—O12—C13−2.85 (17)
C5—C6—C7—C8−0.55 (17)O9—C10—O12—C13176.18 (8)
O9—C6—C7—C8175.12 (10)C10—O12—C13—C14177.84 (9)
C6—C7—C8—C3−0.12 (17)C10—O12—C13—C15−64.35 (12)
C4—C3—C8—C70.86 (17)C10—O12—C13—C1659.67 (12)
C2—C3—C8—C7−177.20 (10)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BH2315).

References

  • Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19.
  • Atwood, J. L. & Barbour, L. J. (2003). Cryst. Growth. Des.3, 3–8.
  • Barbour, L. J. (2001). J. Supramol. Chem.1, 189–191.
  • Bruker (2009). APEX2, SAINT and SADABS Bruker AXS Inc., Madison, Wisconsin, USA.
  • Girard, M., Murphy, P. & Tsou, N. N. (2005). Tetrahedron Lett.46, 2449–2452.
  • Nagata, Y., Otaka, H. & Chujo, Y. (2008). Macromolecules, 41, 737–740.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]

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