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Acta Crystallogr Sect E Struct Rep Online. 2009 June 1; 65(Pt 6): o1363.
Published online 2009 May 23. doi:  10.1107/S1600536809017887
PMCID: PMC2969800

Phenyl N-phenyl­carbamate

Abstract

In the title compound, C13H11NO2, the aromatic rings are oriented at a dihedral angle of 42.52 (12)°. The crystal structure is stabilized by inter­molecular N—H(...)O hydrogen bonds, which form infinite one-dimensional polymeric chains extending along the a axis. C—H(...)π inter­actions between the aromatic rings are also present.

Related literature

For related structures, see: Haufe et al. (2003 [triangle]); Shah et al. (2008 [triangle], 2009 [triangle]); Xu & Qu (2008 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-o1363-scheme1.jpg

Experimental

Crystal data

  • C13H11NO2
  • M r = 213.23
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-65-o1363-efi1.jpg
  • a = 9.4734 (9) Å
  • b = 19.5825 (17) Å
  • c = 5.8509 (5) Å
  • V = 1085.42 (17) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.09 mm−1
  • T = 296 K
  • 0.22 × 0.12 × 0.12 mm

Data collection

  • Bruker Kappa APEXII CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2005 [triangle]) T min = 0.985, T max = 0.988
  • 6579 measured reflections
  • 1505 independent reflections
  • 751 reflections with I > 2σ(I)
  • R int = 0.071

Refinement

  • R[F 2 > 2σ(F 2)] = 0.046
  • wR(F 2) = 0.086
  • S = 0.97
  • 1505 reflections
  • 145 parameters
  • 1 restraint
  • H-atom parameters constrained
  • Δρmax = 0.13 e Å−3
  • Δρmin = −0.17 e Å−3

Data collection: APEX2 (Bruker, 2007 [triangle]); cell refinement: SAINT (Bruker, 2007 [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: ORTEP-3 for Windows (Farrugia, 1997 [triangle]) and PLATON (Spek, 2009 [triangle]); software used to prepare material for publication: WinGX (Farrugia, 1999 [triangle]) and PLATON.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809017887/at2785sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809017887/at2785Isup2.hkl

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

Acknowledgments

NA gratefully acknowledges the Higher Education Commission, Islamabad, Pakistan, for providing a scholarship under the Indigenous PhD Program (PIN 042-120599-PS2-156).

supplementary crystallographic information

Comment

The title compound (I), (Fig. 1), is synthesized for investigation of biological activity like enzyme inhibition and antimicrobial activity. It is one of the members of a series of carbamates being synthesized in our laboratory.

Various crystal structures of N-phenylcarbamates with different attachments have been reported. Examples include (II) 4-nitrophenyl N-phenylcarbamate (Xu & Qu, 2008), (III) cis-4-fluorocyclohexyl N-phenylcarbamate, cis-4-hydroxycyclohexyl N-phenylcarbamate and 4-oxocyclohexyl N-phenylcarbamate (Haufe et al., 2003). The title compound is a N-phenylcarbamate with the simplest type of aromatic ring. In (I), the rings A (C1—C6) and B (C8—C13) are oriented at a dihedral angle of 42.49 (13)°. The title compound is stabilized in the form of infinite one-dimensional polymeric chains due to intermolecular N—H···O H-bonding. These chains extend along the crystallographic a axis (Table 1, Fig. 2). Similar infinite chains also due to intermolecular N—H···O H-bonding have also been found in 3-[(3,4-dichlorophenyl)aminocarbonyl]-propionic acid (Shah et al., 2009), 4-[(2-fluorophenyl)amino]-4-oxobutanoic acid (Shah et al., 2008). The packing may also be stabilized due to C—H···π interactions (Table 1).

Experimental

A solution of aniline (0.913 ml, 0.01 mol) and dichloromethane (20 ml) was prepared. Phenylchloroformate (1.26 ml, 0.01 mol) was added dropwise to the magnetically stirring solution. The mixture turned to a suspension after 1 h due to stirring at room temperature. To obtain the final product, n-hexane (30 ml) was added and a precipitate was formed. The precipitate was filtered and recrystalized from ethylacetate and methanol (9:1).

Refinement

In the absence of significant anomalous scattering effects, Friedel pairs were merged. H-atoms were positioned geometrically, with N—H = 0.86 Å and C—H = 0.93 Å for aromatic rings and constrained to ride on their parent atoms, with Uiso(H) = xUeq(C, N), where x = 1.2 for all H atoms.

Figures

Fig. 1.
View of the title compound with the atom numbering scheme. The thermal ellipsoids are drawn at the 50% probability level. H-atoms are shown as small circles of arbitrary radii.
Fig. 2.
A partial packing diagram showing infinite one-dimensional chains along the a axis.

Crystal data

C13H11NO2F(000) = 448
Mr = 213.23Dx = 1.305 Mg m3
Orthorhombic, Pna21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2nCell parameters from 2241 reflections
a = 9.4734 (9) Åθ = 3.0–28.6°
b = 19.5825 (17) ŵ = 0.09 mm1
c = 5.8509 (5) ÅT = 296 K
V = 1085.42 (17) Å3Needle, colourless
Z = 40.22 × 0.12 × 0.12 mm

Data collection

Bruker Kappa APEXII CCD diffractometer1505 independent reflections
Radiation source: fine-focus sealed tube751 reflections with I > 2σ(I)
graphiteRint = 0.071
Detector resolution: 7.40 pixels mm-1θmax = 28.6°, θmin = 3.0°
ω scansh = −12→12
Absorption correction: multi-scan (SADABS; Bruker, 2005)k = −26→26
Tmin = 0.985, Tmax = 0.988l = −4→7
6579 measured reflections

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) = 0.086H-atom parameters constrained
S = 0.97w = 1/[σ2(Fo2) + (0.028P)2] where P = (Fo2 + 2Fc2)/3
1505 reflections(Δ/σ)max < 0.001
145 parametersΔρmax = 0.13 e Å3
1 restraintΔρmin = −0.16 e Å3

Special details

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles
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
O10.2597 (2)0.32604 (11)0.9484 (4)0.0567 (9)
O20.0419 (2)0.29274 (9)0.8340 (5)0.0516 (8)
N10.2427 (3)0.23828 (12)0.7187 (5)0.0452 (10)
C10.2055 (3)0.37847 (16)1.0868 (7)0.0443 (14)
C20.2411 (4)0.44407 (15)1.0327 (7)0.0510 (14)
C30.2016 (4)0.49574 (16)1.1764 (7)0.0573 (15)
C40.1281 (4)0.48187 (15)1.3717 (7)0.0553 (14)
C50.0927 (4)0.41549 (16)1.4235 (7)0.0550 (14)
C60.1333 (4)0.36338 (15)1.2818 (7)0.0489 (13)
C70.1675 (3)0.28518 (15)0.8343 (7)0.0422 (11)
C80.1863 (3)0.19143 (14)0.5605 (7)0.0414 (13)
C90.0627 (3)0.15661 (14)0.5992 (6)0.0486 (13)
C100.0146 (4)0.11085 (16)0.4366 (8)0.0633 (18)
C110.0904 (5)0.09913 (18)0.2388 (8)0.0700 (16)
C120.2135 (5)0.13340 (19)0.2040 (7)0.0667 (18)
C130.2617 (4)0.17989 (15)0.3606 (7)0.0548 (13)
H10.332130.236770.743300.0544*
H20.291560.453480.900070.0616*
H30.224910.540631.140820.0689*
H40.102160.517151.469470.0664*
H50.041080.405991.554890.0657*
H60.111840.318331.318180.0584*
H90.011970.163700.733130.0581*
H10−0.069850.087730.460830.0757*
H110.057690.068140.130630.0838*
H120.265570.125160.072080.0799*
H130.344900.203720.333040.0658*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.0340 (14)0.0611 (13)0.0751 (19)−0.0041 (12)0.0042 (13)−0.0266 (14)
O20.0283 (12)0.0562 (12)0.0702 (18)0.0033 (11)−0.0034 (13)−0.0119 (12)
N10.0287 (15)0.0489 (15)0.058 (2)0.0041 (14)−0.0041 (15)−0.0099 (15)
C10.032 (2)0.052 (2)0.049 (3)−0.0012 (16)−0.003 (2)−0.0058 (19)
C20.050 (2)0.054 (2)0.049 (3)−0.0063 (18)0.000 (2)0.0073 (19)
C30.059 (3)0.0410 (19)0.072 (3)−0.0043 (17)−0.002 (2)0.006 (2)
C40.053 (2)0.049 (2)0.064 (3)0.0016 (17)−0.001 (2)−0.0118 (19)
C50.055 (2)0.059 (2)0.051 (3)−0.0031 (17)0.006 (2)0.001 (2)
C60.048 (2)0.0386 (17)0.060 (3)−0.0006 (16)−0.002 (2)0.0033 (19)
C70.040 (2)0.0385 (15)0.048 (2)−0.0018 (17)−0.007 (2)0.0020 (17)
C80.039 (2)0.0362 (17)0.049 (3)0.0063 (15)−0.006 (2)−0.0044 (17)
C90.043 (2)0.0437 (17)0.059 (3)−0.0001 (16)−0.0045 (19)−0.0024 (18)
C100.049 (3)0.053 (2)0.088 (4)−0.0040 (18)−0.021 (3)−0.008 (2)
C110.079 (3)0.062 (2)0.069 (3)0.014 (2)−0.024 (3)−0.022 (2)
C120.077 (4)0.069 (2)0.054 (3)0.019 (2)−0.002 (3)−0.012 (2)
C130.052 (2)0.0485 (18)0.064 (3)0.0044 (17)0.007 (2)−0.004 (2)

Geometric parameters (Å, °)

O1—C11.405 (4)C9—C101.384 (5)
O1—C71.360 (4)C10—C111.381 (6)
O2—C71.199 (3)C11—C121.361 (6)
N1—C71.345 (4)C12—C131.370 (5)
N1—C81.409 (4)C2—H20.9300
N1—H10.8600C3—H30.9300
C1—C21.365 (4)C4—H40.9300
C1—C61.363 (5)C5—H50.9300
C2—C31.368 (5)C6—H60.9300
C3—C41.365 (6)C9—H90.9300
C4—C51.376 (4)C10—H100.9300
C5—C61.370 (5)C11—H110.9300
C8—C131.389 (5)C12—H120.9300
C8—C91.374 (4)C13—H130.9300
O2···C63.087 (5)C10···H3ix3.0700
O2···C93.005 (4)C13···H6iii3.0700
O2···N1i2.976 (3)H1···H132.4900
O1···H9ii2.7100H1···O2ii2.1400
O2···H5iii2.7500H1···H9ii2.5900
O2···H92.6100H3···C9x3.0400
O2···H1i2.1400H3···C10x3.0700
N1···O2ii2.976 (3)H4···H12xi2.5300
C1···C10iv3.579 (5)H5···O2v2.7500
C5···C7v3.576 (5)H5···C3xii3.0800
C6···O23.087 (5)H6···C72.9500
C6···C7v3.592 (6)H6···C8v2.9500
C7···C6iii3.592 (6)H6···C13v3.0700
C7···C5iii3.576 (5)H6···H13viii2.5700
C9···O23.005 (4)H9···O22.6100
C10···C1vi3.579 (5)H9···C72.8600
C2···H11iv3.0600H9···O1i2.7100
C3···H5vii3.0800H9···H1i2.5900
C6···H13viii3.0500H11···C2vi3.0600
C7···H92.8600H12···H4xiii2.5300
C7···H62.9500H13···H12.4900
C8···H6iii2.9500H13···C6xiv3.0500
C9···H3ix3.0400H13···H6xiv2.5700
C1—O1—C7118.6 (2)C8—C13—C12120.0 (3)
C7—N1—C8125.1 (3)C1—C2—H2120.00
C7—N1—H1117.00C3—C2—H2120.00
C8—N1—H1117.00C2—C3—H3120.00
O1—C1—C2117.6 (3)C4—C3—H3120.00
O1—C1—C6120.5 (3)C3—C4—H4120.00
C2—C1—C6121.5 (3)C5—C4—H4120.00
C1—C2—C3119.1 (4)C4—C5—H5120.00
C2—C3—C4120.5 (3)C6—C5—H5120.00
C3—C4—C5119.8 (3)C1—C6—H6120.00
C4—C5—C6120.1 (4)C5—C6—H6120.00
C1—C6—C5119.1 (3)C8—C9—H9120.00
O1—C7—O2124.4 (3)C10—C9—H9120.00
O1—C7—N1108.0 (2)C9—C10—H10120.00
O2—C7—N1127.5 (3)C11—C10—H10120.00
N1—C8—C9122.6 (3)C10—C11—H11120.00
C9—C8—C13119.8 (3)C12—C11—H11120.00
N1—C8—C13117.7 (3)C11—C12—H12120.00
C8—C9—C10119.3 (3)C13—C12—H12120.00
C9—C10—C11120.8 (3)C8—C13—H13120.00
C10—C11—C12119.3 (4)C12—C13—H13120.00
C11—C12—C13120.9 (4)
C7—O1—C1—C2−119.0 (3)C1—C2—C3—C40.3 (6)
C7—O1—C1—C668.1 (4)C2—C3—C4—C5−0.4 (6)
C1—O1—C7—O23.9 (5)C3—C4—C5—C61.2 (6)
C1—O1—C7—N1−178.6 (3)C4—C5—C6—C1−1.8 (6)
C8—N1—C7—O1−172.7 (3)N1—C8—C9—C10−179.4 (3)
C7—N1—C8—C13138.2 (3)C13—C8—C9—C10−0.6 (5)
C8—N1—C7—O24.7 (6)N1—C8—C13—C12178.2 (3)
C7—N1—C8—C9−43.0 (5)C9—C8—C13—C12−0.7 (5)
O1—C1—C2—C3−173.7 (3)C8—C9—C10—C111.1 (5)
C2—C1—C6—C51.6 (6)C9—C10—C11—C12−0.3 (6)
C6—C1—C2—C3−0.9 (6)C10—C11—C12—C13−1.0 (6)
O1—C1—C6—C5174.2 (3)C11—C12—C13—C81.5 (6)

Symmetry codes: (i) x−1/2, −y+1/2, z; (ii) x+1/2, −y+1/2, z; (iii) x, y, z−1; (iv) x+1/2, −y+1/2, z+1; (v) x, y, z+1; (vi) x−1/2, −y+1/2, z−1; (vii) −x, −y+1, z−1/2; (viii) x−1/2, −y+1/2, z+1; (ix) −x+1/2, y−1/2, z−1/2; (x) −x+1/2, y+1/2, z+1/2; (xi) −x+1/2, y+1/2, z+3/2; (xii) −x, −y+1, z+1/2; (xiii) −x+1/2, y−1/2, z−3/2; (xiv) x+1/2, −y+1/2, z−1.

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N1—H1···O2ii0.86002.14002.976 (3)165.00
C3—H3···Cg2x0.93002.80003.673 (4)156.00
C10—H10···Cg1vi0.93002.86003.599 (4)137.00

Symmetry codes: (ii) x+1/2, −y+1/2, z; (x) −x+1/2, y+1/2, z+1/2; (vi) x−1/2, −y+1/2, z−1.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: AT2785).

References

  • Bruker (2005). SADABS Bruker AXS Inc., Madison, Wisconsin, USA.
  • Bruker (2007). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Farrugia, L. J. (1997). J. Appl. Cryst.30, 565.
  • Farrugia, L. J. (1999). J. Appl. Cryst.32, 837–838.
  • Haufe, G., Pietz, S., Wolker, D. & Frohlich, R. (2003). Eur. J. Org. Chem. pp. 2166–2175.
  • Shah, F. A., Tahir, M. N. & Ali, S. (2008). Acta Cryst. E64, o1661. [PMC free article] [PubMed]
  • Shah, F. A., Tahir, M. N., Ali, S., Ahmed, S. & Danish, M. (2009). Acta Cryst. E65, o1130. [PMC free article] [PubMed]
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Spek, A. L. (2009). Acta Cryst. D65, 148–155. [PMC free article] [PubMed]
  • Xu, Y.-H. & Qu, F. (2008). Acta Cryst. E64, o404. [PMC free article] [PubMed]

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