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Acta Crystallogr Sect E Struct Rep Online. 2009 July 1; 65(Pt 7): o1629.
Published online 2009 June 20. doi:  10.1107/S1600536809022788
PMCID: PMC2969480

Phenyl N-(2-methyl­phen­yl)carbamate

Abstract

In the title compound, C14H13NO2, the aromatic rings attached to the O and N atoms make dihedral angles of 62.65 (9) and 38.28 (11)°, respectively, with the central carbamate group. The benzene rings are oriented at a dihedral angle of 39.22 (10)°. In the crystal, a very weak C—H(...)π inter­action occurs.

Related literature

For a related structure, see: Shahwar et al. (2009 [triangle]).

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Object name is e-65-o1629-scheme1.jpg

Experimental

Crystal data

  • C14H13NO2
  • M r = 227.25
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-65-o1629-efi1.jpg
  • a = 10.5736 (9) Å
  • b = 18.5414 (14) Å
  • c = 5.9681 (4) Å
  • V = 1170.04 (15) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.09 mm−1
  • T = 296 K
  • 0.25 × 0.14 × 0.14 mm

Data collection

  • Bruker Kappa APEXII CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2005 [triangle]) T min = 0.984, T max = 0.989
  • 6929 measured reflections
  • 1585 independent reflections
  • 997 reflections with I > 2σ(I)
  • R int = 0.037

Refinement

  • R[F 2 > 2σ(F 2)] = 0.039
  • wR(F 2) = 0.083
  • S = 1.01
  • 1585 reflections
  • 158 parameters
  • 1 restraint
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.13 e Å−3
  • Δρmin = −0.15 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 (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/S1600536809022788/hb5008sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809022788/hb5008Isup2.hkl

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

Acknowledgments

NA greatfully 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

We have recently published the crystal structure of (II), phenyl N-phenylcarbamate (Shahwar et al., 2009), which differs from the title compound, (I), due to an attachement of CH3 at ortho-position of benzene ring attached with N-atom.

In (I), the benzene rings A (C1—C6) and B (C8—C13) are of course planar. The central portion containing carbamate group C (C7/O1/O2/N1) is also planar. The benzene rings A & B are oriented at a dihedral angle of 39.22 (10)°. The dihedral angles between A/C and B/C have values of of 62.65 (9)° and 38.28 (11)°, respectively. The H-atom attached with N-atom does not form any intera or inter-molecular H-bonding due to the attachement of methyl group. There exists a weak C–H···π interaction (Table 1).

Experimental

A solution of o-toluidine (1.08 ml, 0.01 mol) in dichloromethane (20 ml) was prepared. Phenylchloroformate (1.26 ml, 0.01 mol) was added drop-wise to the magnetically stirring solution. The mixture turned to suspension after one hour. To get complete product, n-hexane (30 ml) was added and the precipitate were obtained. The precipitate were filtered out and recrystalized from ethylacetate and methanol (9:1) to yield colourless blocks of (I).

Refinement

In the absence of significant anomalous scattering effects, Friedel pairs were merged before refinement.

The coordinates of the N-bound H atom were refined. The C-bound H atoms were positioned geometrically (C—H = 0.93–0.96 Å) and refined as riding with Uiso(H) = 1.2Ueq(C, N) or 1.5Ueq(methyl C).

Figures

Fig. 1.
View of (I) with displacement ellipsoids drawn at the 50% probability level. H-atoms are shown by small spheres of arbitrary radius.

Crystal data

C14H13NO2F(000) = 480
Mr = 227.25Dx = 1.290 Mg m3
Orthorhombic, Pna21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2nCell parameters from 2241 reflections
a = 10.5736 (9) Åθ = 3.0–28.6°
b = 18.5414 (14) ŵ = 0.09 mm1
c = 5.9681 (4) ÅT = 296 K
V = 1170.04 (15) Å3Block, colourless
Z = 40.25 × 0.14 × 0.14 mm

Data collection

Bruker Kappa APEXII CCD diffractometer1585 independent reflections
Radiation source: fine-focus sealed tube997 reflections with I > 2σ(I)
graphiteRint = 0.037
Detector resolution: 7.40 pixels mm-1θmax = 28.3°, θmin = 2.9°
ω scansh = −14→13
Absorption correction: multi-scan (SADABS; Bruker, 2005)k = −17→24
Tmin = 0.984, Tmax = 0.989l = −7→7
6929 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)] = 0.039Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.083H atoms treated by a mixture of independent and constrained refinement
S = 1.01w = 1/[σ2(Fo2) + (0.0377P)2] where P = (Fo2 + 2Fc2)/3
1585 reflections(Δ/σ)max < 0.001
158 parametersΔρmax = 0.13 e Å3
1 restraintΔρmin = −0.15 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
O10.27882 (15)0.33744 (9)0.6965 (3)0.0594 (6)
O20.48038 (14)0.30458 (9)0.6133 (3)0.0585 (6)
N10.30983 (19)0.24161 (11)0.4867 (3)0.0547 (7)
C10.31727 (19)0.39161 (13)0.8463 (4)0.0459 (8)
C20.3813 (2)0.37450 (12)1.0394 (4)0.0492 (8)
C30.4089 (2)0.42831 (13)1.1897 (4)0.0550 (9)
C40.3718 (2)0.49827 (14)1.1487 (5)0.0610 (9)
C50.3068 (2)0.51391 (15)0.9561 (4)0.0657 (10)
C60.2797 (2)0.46077 (14)0.8027 (4)0.0580 (9)
C70.3691 (2)0.29463 (12)0.6005 (4)0.0472 (8)
C80.3694 (2)0.19088 (12)0.3442 (4)0.0479 (7)
C90.3097 (2)0.17293 (13)0.1431 (4)0.0508 (8)
C100.3682 (3)0.12288 (15)0.0089 (4)0.0683 (10)
C110.4814 (3)0.09134 (15)0.0662 (6)0.0783 (12)
C120.5378 (3)0.10948 (16)0.2643 (6)0.0746 (11)
C130.4824 (2)0.15870 (14)0.4054 (5)0.0599 (9)
C140.1842 (2)0.20522 (15)0.0812 (5)0.0670 (10)
H10.233 (2)0.2453 (13)0.486 (5)0.0657*
H20.405700.327181.067870.0590*
H30.452900.417431.320270.0660*
H40.390620.534591.250890.0732*
H50.280800.561010.928700.0787*
H60.236410.471700.671390.0696*
H100.330000.10987−0.125450.0820*
H110.519130.05797−0.029010.0938*
H120.614320.088300.303940.0895*
H130.520510.170340.541110.0718*
H14A0.123020.193690.194470.1006*
H14B0.156950.18596−0.060110.1006*
H14C0.192490.256650.069560.1006*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.0456 (10)0.0665 (11)0.0662 (11)0.0037 (8)−0.0135 (9)−0.0153 (10)
O20.0448 (10)0.0669 (11)0.0638 (10)−0.0087 (8)−0.0047 (9)−0.0083 (9)
N10.0419 (11)0.0632 (13)0.0591 (12)−0.0031 (11)−0.0084 (12)−0.0090 (11)
C10.0369 (12)0.0511 (14)0.0497 (14)−0.0005 (10)−0.0010 (11)0.0007 (12)
C20.0439 (13)0.0417 (13)0.0620 (15)−0.0029 (11)−0.0062 (11)0.0052 (12)
C30.0509 (15)0.0604 (16)0.0538 (14)−0.0063 (12)−0.0084 (12)−0.0008 (14)
C40.0625 (15)0.0521 (15)0.0683 (18)−0.0070 (12)0.0069 (14)−0.0096 (14)
C50.0692 (19)0.0490 (15)0.079 (2)0.0116 (13)0.0064 (15)0.0095 (15)
C60.0577 (16)0.0621 (17)0.0541 (16)0.0100 (13)−0.0013 (13)0.0092 (14)
C70.0484 (14)0.0513 (14)0.0418 (11)−0.0019 (12)−0.0080 (12)0.0035 (11)
C80.0445 (13)0.0489 (13)0.0503 (12)−0.0100 (12)−0.0001 (12)0.0023 (12)
C90.0479 (14)0.0562 (14)0.0484 (14)−0.0180 (11)0.0020 (11)0.0013 (13)
C100.0679 (19)0.0809 (19)0.0562 (16)−0.0237 (16)0.0076 (15)−0.0113 (15)
C110.070 (2)0.072 (2)0.093 (2)−0.0072 (16)0.0194 (18)−0.0196 (17)
C120.0536 (17)0.0682 (19)0.102 (2)0.0007 (15)0.0057 (17)−0.0014 (18)
C130.0509 (16)0.0598 (17)0.0689 (16)−0.0023 (12)−0.0067 (13)0.0042 (14)
C140.0568 (15)0.084 (2)0.0601 (14)−0.0133 (14)−0.0147 (13)0.0003 (15)

Geometric parameters (Å, °)

O1—C11.405 (3)C10—C111.375 (4)
O1—C71.367 (3)C11—C121.366 (5)
O2—C71.194 (3)C12—C131.373 (4)
N1—C71.349 (3)C2—H20.9300
N1—C81.416 (3)C3—H30.9300
N1—H10.82 (2)C4—H40.9300
C1—C61.367 (3)C5—H50.9300
C1—C21.374 (3)C6—H60.9300
C2—C31.373 (3)C10—H100.9300
C3—C41.377 (4)C11—H110.9300
C4—C51.370 (4)C12—H120.9300
C5—C61.375 (4)C13—H130.9300
C8—C131.385 (3)C14—H14A0.9600
C8—C91.396 (3)C14—H14B0.9600
C9—C101.373 (4)C14—H14C0.9600
C9—C141.502 (3)
C1—O1—C7118.67 (17)C1—C2—H2121.00
C7—N1—C8125.43 (19)C3—C2—H2120.00
C8—N1—H1119.7 (19)C2—C3—H3120.00
C7—N1—H1113.9 (18)C4—C3—H3120.00
O1—C1—C6117.7 (2)C3—C4—H4120.00
C2—C1—C6121.3 (2)C5—C4—H4120.00
O1—C1—C2120.8 (2)C4—C5—H5120.00
C1—C2—C3119.0 (2)C6—C5—H5120.00
C2—C3—C4120.5 (2)C1—C6—H6121.00
C3—C4—C5119.4 (2)C5—C6—H6120.00
C4—C5—C6120.8 (2)C9—C10—H10119.00
C1—C6—C5119.0 (2)C11—C10—H10119.00
O1—C7—N1108.04 (18)C10—C11—H11120.00
O2—C7—N1127.1 (2)C12—C11—H11120.00
O1—C7—O2124.9 (2)C11—C12—H12120.00
C9—C8—C13120.9 (2)C13—C12—H12120.00
N1—C8—C9118.26 (19)C8—C13—H13120.00
N1—C8—C13120.8 (2)C12—C13—H13120.00
C10—C9—C14121.6 (2)C9—C14—H14A109.00
C8—C9—C10117.3 (2)C9—C14—H14B109.00
C8—C9—C14121.1 (2)C9—C14—H14C109.00
C9—C10—C11122.3 (3)H14A—C14—H14B109.00
C10—C11—C12119.4 (3)H14A—C14—H14C109.00
C11—C12—C13120.5 (3)H14B—C14—H14C109.00
C8—C13—C12119.5 (3)
C7—O1—C1—C2−60.4 (3)C3—C4—C5—C6−0.8 (3)
C7—O1—C1—C6124.9 (2)C4—C5—C6—C10.8 (3)
C1—O1—C7—O2−9.1 (3)N1—C8—C9—C10−179.1 (2)
C1—O1—C7—N1172.51 (19)N1—C8—C9—C14−1.3 (3)
C8—N1—C7—O1172.7 (2)C13—C8—C9—C10−0.6 (4)
C8—N1—C7—O2−5.7 (4)C13—C8—C9—C14177.2 (2)
C7—N1—C8—C9−139.0 (2)N1—C8—C13—C12179.8 (2)
C7—N1—C8—C1342.5 (3)C9—C8—C13—C121.3 (4)
O1—C1—C2—C3−175.14 (19)C8—C9—C10—C11−0.4 (4)
C6—C1—C2—C3−0.7 (3)C14—C9—C10—C11−178.2 (3)
O1—C1—C6—C5174.57 (19)C9—C10—C11—C120.7 (5)
C2—C1—C6—C5−0.1 (3)C10—C11—C12—C130.0 (5)
C1—C2—C3—C40.7 (3)C11—C12—C13—C8−1.0 (4)
C2—C3—C4—C50.0 (3)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C5—H5···CgBi0.932.953.714 (3)140

Symmetry codes: (i) −x+1/2, y+1/2, z+1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB5008).

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.
  • Shahwar, D., Tahir, M. N., Mughal, M. S., Khan, M. A. & Ahmad, N. (2009). Acta Cryst. E65, o1363. [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]

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