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

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ISSN: 2056-9890

tert-Butyl 4-cyano­phenyl carbonate

aDepartment of Chemistry and Polymer Science, Stellenbosch University, Private Bag X1, Matieland 7602, South Africa
*Correspondence e-mail: malcolma@sun.ac.za

(Received 15 September 2010; accepted 27 September 2010; online 30 September 2010)

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[Girard, M., Murphy, P. & Tsou, N. N. (2005). Tetrahedron Lett. 46, 2449-2452.]); Nagata et al. (2008[Nagata, Y., Otaka, H. & Chujo, Y. (2008). Macromolecules, 41, 737-740.]). For reference structural data, see: Allen et al. (1987[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.]).

[Scheme 1]

Experimental

Crystal data
  • C12H13NO3

  • Mr = 219.23

  • Monoclinic, P 21 /c

  • 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[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.959, Tmax = 0.989

  • 6536 measured reflections

  • 2427 independent reflections

  • 2100 reflections with I > 2σ(I)

  • Rint = 0.017

Refinement
  • R[F2 > 2σ(F2)] = 0.034

  • wR(F2) = 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[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. 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: X-SEED (Barbour, 2001[Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.]; Atwood & Barbour, 2003[Atwood, J. L. & Barbour, L. J. (2003). Cryst. Growth. Des. 3, 3-8.]); software used to prepare material for publication: X-SEED (Barbour, 2001[Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.]; Atwood & Barbour, 2003[Atwood, J. L. & Barbour, L. J. (2003). Cryst. Growth. Des. 3, 3-8.]).

Supporting information


Comment top

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.

Related literature top

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

Experimental top

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 top

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).

Computing details top

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

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound showing the 50% probability ellipsoids for non-H atoms.
[Figure 2] 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.
tert-Butyl 4-cyanophenyl carbonate top
Crystal data top
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 top
Bruker APEX CCD area-detector
diffractometer
2427 independent reflections
Radiation source: fine-focus sealed tube2100 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.017
ω scansθmax = 27.9°, θmin = 2.1°
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
h = 77
Tmin = 0.959, Tmax = 0.989k = 1814
6536 measured reflectionsl = 1715
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)] = 0.034Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.091H-atom parameters constrained
S = 1.05 w = 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
Crystal data top
C12H13NO3V = 1110.1 (2) Å3
Mr = 219.23Z = 4
Monoclinic, P21/cMo Kα radiation
a = 5.7347 (7) ŵ = 0.10 mm1
b = 14.3237 (16) ÅT = 296 K
c = 13.7727 (16) Å0.45 × 0.25 × 0.12 mm
β = 101.110 (1)°
Data collection top
Bruker APEX CCD area-detector
diffractometer
2427 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
2100 reflections with I > 2σ(I)
Tmin = 0.959, Tmax = 0.989Rint = 0.017
6536 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0340 restraints
wR(F2) = 0.091H-atom parameters constrained
S = 1.05Δρmax = 0.31 e Å3
2427 reflectionsΔρmin = 0.23 e Å3
148 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
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) top
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, º) top
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—C50.93 (17)C7—C6—O9—C10105.80 (12)
C2—C3—C4—C5177.14 (10)C5—C6—O9—C1078.37 (13)
C3—C4—C5—C60.27 (17)C6—O9—C10—O115.43 (16)
C4—C5—C6—C70.48 (17)C6—O9—C10—O12175.49 (9)
C4—C5—C6—O9175.16 (10)O11—C10—O12—C132.85 (17)
C5—C6—C7—C80.55 (17)O9—C10—O12—C13176.18 (8)
O9—C6—C7—C8175.12 (10)C10—O12—C13—C14177.84 (9)
C6—C7—C8—C30.12 (17)C10—O12—C13—C1564.35 (12)
C4—C3—C8—C70.86 (17)C10—O12—C13—C1659.67 (12)
C2—C3—C8—C7177.20 (10)

Experimental details

Crystal data
Chemical formulaC12H13NO3
Mr219.23
Crystal system, space groupMonoclinic, P21/c
Temperature (K)296
a, b, c (Å)5.7347 (7), 14.3237 (16), 13.7727 (16)
β (°) 101.110 (1)
V3)1110.1 (2)
Z4
Radiation typeMo Kα
µ (mm1)0.10
Crystal size (mm)0.45 × 0.25 × 0.12
Data collection
DiffractometerBruker APEX CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2009)
Tmin, Tmax0.959, 0.989
No. of measured, independent and
observed [I > 2σ(I)] reflections
6536, 2427, 2100
Rint0.017
(sin θ/λ)max1)0.658
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.034, 0.091, 1.05
No. of reflections2427
No. of parameters148
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.31, 0.23

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001; Atwood & Barbour, 2003).

 

Acknowledgements

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.

References

First citationAllen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19.  CrossRef Web of Science Google Scholar
First citationAtwood, J. L. & Barbour, L. J. (2003). Cryst. Growth. Des. 3, 3–8.  Web of Science CrossRef CAS Google Scholar
First citationBarbour, L. J. (2001). J. Supramol. Chem. 1, 189–191.  CrossRef CAS Google Scholar
First citationBruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationGirard, M., Murphy, P. & Tsou, N. N. (2005). Tetrahedron Lett. 46, 2449–2452.  Web of Science CSD CrossRef CAS Google Scholar
First citationNagata, Y., Otaka, H. & Chujo, Y. (2008). Macromolecules, 41, 737–740.  Web of Science CSD CrossRef CAS Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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