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Acta Crystallogr Sect E Struct Rep Online. 2009 August 1; 65(Pt 8): o1997.
Published online 2009 July 25. doi:  10.1107/S1600536809028785
PMCID: PMC2977260

Phenyl N-(4-methoxy­phen­yl)carbamate

Abstract

The asymmetric unit of the title compound, C14H13NO3, contains two crystallographically independent mol­ecules, in which the aromatic rings are oriented at dihedral angles of 75.64 (3) and 83.14 (3)°. An N—H(...)O hydrogen bond links the two mol­ecules. Weak intramolecular C—H(...)O inter­actions are observed in the two mol­ecules. In the crystal structure, inter­molecular N—H(...)O and C—H(...)O inter­actions link the mol­ecules into a two-dimensional network.

Related literature

For bond-length data, see: Allen et al. (1987 [triangle]).

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Object name is e-65-o1997-scheme1.jpg

Experimental

Crystal data

  • C14H13NO3
  • M r = 243.25
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o1997-efi1.jpg
  • a = 9.869 (2) Å
  • b = 10.870 (2) Å
  • c = 23.319 (5) Å
  • β = 100.27 (3)°
  • V = 2461.5 (9) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 0.09 mm−1
  • T = 294 K
  • 0.30 × 0.20 × 0.10 mm

Data collection

  • Enraf–Nonius CAD-4 diffractometer
  • Absorption correction: ψ scan (North et al., 1968 [triangle]) T min = 0.973, T max = 0.991
  • 4733 measured reflections
  • 4459 independent reflections
  • 2109 reflections with I > 2σ(I)
  • R int = 0.045
  • 3 standard reflections frequency: 120 min intensity decay: 1%

Refinement

  • R[F 2 > 2σ(F 2)] = 0.069
  • wR(F 2) = 0.184
  • S = 1.03
  • 4459 reflections
  • 319 parameters
  • H-atom parameters constrained
  • Δρmax = 0.43 e Å−3
  • Δρmin = −0.34 e Å−3

Data collection: CAD-4 Software (Enraf–Nonius, 1989 [triangle]); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995 [triangle]); 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: SHELXL97.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809028785/hk2744sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809028785/hk2744Isup2.hkl

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

Acknowledgments

The authors thank the Center of Testing and Analysis, Nanjing University for the support.

supplementary crystallographic information

Comment

Some derivatives of benzoic acid are important chemical materials. We report herein the crystal structure of the title compound.

The asymmetric unit of the title compound contains two crystallographically independent molecules (Fig. 1), in which the bond lengths (Allen et al., 1987) and angles are within normal ranges. Rings A (C1-C6), B (C8-C13) and C (C15-C20), D (C22-C27) are, of course, planar and they are oriented at dihedral angles of A/B = 75.64 (3) and C/D = 83.14 (3)°. Intramolecular N-H···O hydrogen bond (Table 1) link the two molecules (Fig. 1). There also exist two intramolecular C-H···O interactions (Table 1).

In the crystal structure, intramolecular N-H···O and intermolecular N-H···O and C-H···O interactions (Table 1) link the molecules into a two dimensional network (Fig. 2), in which they may be effective in the stabilization of the structure.

Experimental

For the preparation of the title compound, to a cold stirring solution of 4-methoxybenzenamine (1.0 g) and triethylamine (0.8 ml) in methylene chloride (10 ml) was added phenyl chloroformate (1.0 ml) slowly at 273 K. The mixture was then warmed and stirred for 1 h at room temperature. The mixture was washed with water (20 ml), dried over sodium sulfate, and concentrated to near dryness. The crude product was purified by recrystallization from petroleum ether (yield; 1.3 g). Crystals suitable for X-ray analysis were obtained by slow evaporation of a petroleum ether solution.

Refinement

H atoms were positioned geometrically, with N-H = 0.86 Å (for NH) and C-H = 0.93 and 0.96 Å for aromatic and methyl H, respectively, and constrained to ride on their parent atoms, with Uiso(H) = xUeq(C,N), where x = 1.5 for methyl H and x = 1.2 for all other H atoms.

Figures

Fig. 1.
The molecular structure of the title molecule, with the atom-numbering scheme. Hydrogen bond is shown as dashed line.
Fig. 2.
A partial packing diagram of the title compound. Hydrogen bonds are shown as dashed lines.

Crystal data

C14H13NO3F(000) = 1024
Mr = 243.25Dx = 1.313 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 25 reflections
a = 9.869 (2) Åθ = 10–13°
b = 10.870 (2) ŵ = 0.09 mm1
c = 23.319 (5) ÅT = 294 K
β = 100.27 (3)°Block, colorless
V = 2461.5 (9) Å30.30 × 0.20 × 0.10 mm
Z = 8

Data collection

Enraf–Nonius CAD-4 diffractometer2109 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.045
graphiteθmax = 25.3°, θmin = 1.8°
ω/2θ scansh = 0→11
Absorption correction: ψ scan (North et al., 1968)k = 0→13
Tmin = 0.973, Tmax = 0.991l = −28→27
4733 measured reflections3 standard reflections every 120 min
4459 independent reflections intensity decay: 1%

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)] = 0.069Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.184H-atom parameters constrained
S = 1.03w = 1/[σ2(Fo2) + (0.08P)2] where P = (Fo2 + 2Fc2)/3
4459 reflections(Δ/σ)max < 0.001
319 parametersΔρmax = 0.43 e Å3
0 restraintsΔρmin = −0.34 e Å3

Special details

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)

xyzUiso*/Ueq
O11.0212 (2)0.7911 (3)0.03978 (13)0.0894 (8)
O20.8011 (2)0.7329 (2)0.01287 (11)0.0730 (8)
O30.6882 (3)0.3624 (3)−0.20767 (12)0.0811 (8)
O41.4527 (2)0.6417 (3)−0.07369 (12)0.0818 (9)
O51.2693 (2)0.7162 (2)−0.03922 (11)0.0731 (8)
O61.4470 (2)1.1216 (2)0.16973 (11)0.0725 (8)
N10.9696 (3)0.6635 (3)−0.03360 (15)0.0730 (9)
H1A1.05670.6696−0.03310.088*
N21.4897 (3)0.7712 (3)−0.00016 (13)0.0618 (8)
H2B1.57360.7542−0.00260.074*
C10.9618 (5)1.0279 (5)0.1698 (3)0.1066 (17)
H1B0.95381.08510.19860.128*
C21.0165 (5)0.9067 (6)0.1852 (2)0.1185 (18)
H2A1.04090.88240.22390.142*
C31.0310 (4)0.8289 (5)0.1404 (2)0.0975 (15)
H3A1.06680.75050.14860.117*
C40.9940 (3)0.8648 (4)0.08460 (18)0.0628 (10)
C50.9390 (4)0.9807 (4)0.07198 (19)0.0745 (11)
H5A0.91251.00610.03350.089*
C60.9246 (4)1.0556 (5)0.1160 (2)0.0919 (14)
H6A0.88511.13250.10690.110*
C70.9180 (4)0.7285 (4)0.0059 (2)0.0894 (8)
C80.8940 (4)0.5852 (3)−0.07637 (18)0.0628 (10)
C90.7833 (4)0.5173 (4)−0.06612 (18)0.0689 (11)
H9A0.75680.5211−0.02980.083*
C100.7113 (4)0.4439 (4)−0.10902 (17)0.0684 (11)
H10A0.63620.3990−0.10160.082*
C110.7492 (4)0.4364 (4)−0.16274 (18)0.0627 (10)
C120.8617 (4)0.5036 (4)−0.17297 (18)0.0724 (11)
H12A0.88910.4986−0.20900.087*
C130.9328 (4)0.5771 (4)−0.13035 (19)0.0736 (11)
H13A1.00790.6221−0.13780.088*
C140.5858 (5)0.2793 (4)−0.1969 (2)0.0984 (15)
H14A0.55180.2336−0.23170.148*
H14B0.51150.3242−0.18520.148*
H14C0.62450.2236−0.16640.148*
C151.2046 (4)0.4562 (5)−0.2066 (2)0.0894 (14)
H15A1.15040.4138−0.23700.107*
C161.2464 (5)0.5728 (5)−0.2151 (2)0.0938 (14)
H16A1.22030.6100−0.25130.113*
C171.3267 (4)0.6362 (4)−0.17070 (19)0.0764 (12)
H17A1.35530.7160−0.17650.092*
C181.3637 (3)0.5799 (4)−0.11805 (17)0.0645 (11)
C191.3217 (4)0.4635 (4)−0.1092 (2)0.0778 (12)
H19A1.34710.4261−0.07300.093*
C201.2418 (5)0.4019 (4)−0.1541 (3)0.0903 (14)
H20A1.21300.3220−0.14840.108*
C211.3919 (4)0.7121 (3)−0.03685 (16)0.0584 (10)
C221.4700 (3)0.8590 (3)0.04237 (15)0.0526 (9)
C231.5852 (3)0.9022 (4)0.07914 (16)0.0629 (10)
H23A1.67160.87190.07580.075*
C241.5739 (4)0.9892 (4)0.12045 (17)0.0661 (11)
H24A1.65281.01650.14510.079*
C251.4473 (3)1.0370 (3)0.12614 (15)0.0554 (9)
C261.3334 (3)0.9931 (4)0.09065 (16)0.0646 (10)
H26A1.24711.02300.09440.078*
C271.3439 (3)0.9049 (4)0.04911 (17)0.0688 (11)
H27A1.26450.87600.02530.083*
C281.3265 (4)1.1931 (4)0.16771 (19)0.0853 (13)
H28A1.33911.24930.20000.128*
H28B1.24991.14000.16990.128*
H28C1.30891.23860.13190.128*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.0469 (13)0.107 (2)0.118 (2)−0.0070 (13)0.0267 (13)−0.0378 (17)
O20.0419 (13)0.0875 (19)0.092 (2)0.0005 (13)0.0174 (12)−0.0078 (15)
O30.085 (2)0.085 (2)0.0725 (19)−0.0031 (17)0.0130 (15)0.0021 (17)
O40.0475 (14)0.114 (2)0.0847 (19)−0.0007 (15)0.0136 (14)−0.0360 (18)
O50.0390 (14)0.095 (2)0.0863 (19)−0.0060 (14)0.0130 (12)−0.0183 (16)
O60.0538 (15)0.0753 (18)0.0846 (19)0.0041 (14)0.0023 (13)−0.0187 (16)
N10.0414 (16)0.081 (2)0.100 (2)−0.0004 (17)0.0213 (17)−0.009 (2)
N20.0363 (14)0.088 (2)0.0609 (18)0.0009 (16)0.0069 (13)−0.0087 (18)
C10.072 (3)0.141 (4)0.104 (4)−0.021 (3)0.009 (3)−0.049 (4)
C20.098 (4)0.176 (5)0.076 (3)0.010 (4)−0.001 (3)0.023 (3)
C30.083 (3)0.107 (4)0.101 (3)0.033 (3)0.012 (3)0.033 (3)
C40.0358 (18)0.075 (3)0.077 (3)−0.0032 (19)0.0079 (18)−0.004 (2)
C50.058 (2)0.097 (3)0.069 (3)0.009 (2)0.014 (2)0.018 (2)
C60.074 (3)0.083 (3)0.119 (4)−0.010 (3)0.018 (3)−0.008 (3)
C70.0469 (13)0.107 (2)0.118 (2)−0.0070 (13)0.0267 (13)−0.0378 (17)
C80.046 (2)0.059 (2)0.087 (3)0.0060 (19)0.019 (2)0.002 (2)
C90.058 (2)0.079 (3)0.073 (3)−0.001 (2)0.023 (2)0.005 (2)
C100.057 (2)0.081 (3)0.072 (3)−0.005 (2)0.022 (2)0.007 (2)
C110.059 (2)0.057 (2)0.073 (3)0.008 (2)0.011 (2)0.006 (2)
C120.074 (3)0.066 (3)0.084 (3)0.004 (2)0.035 (2)−0.002 (2)
C130.061 (2)0.069 (3)0.100 (3)−0.003 (2)0.039 (2)−0.001 (3)
C140.091 (3)0.102 (4)0.103 (4)−0.026 (3)0.017 (3)0.001 (3)
C150.061 (3)0.111 (4)0.096 (4)−0.008 (3)0.015 (3)−0.037 (3)
C160.086 (3)0.122 (4)0.072 (3)0.000 (3)0.010 (3)0.000 (3)
C170.071 (3)0.081 (3)0.075 (3)−0.014 (2)0.008 (2)0.002 (3)
C180.041 (2)0.088 (3)0.065 (3)0.002 (2)0.0099 (19)−0.014 (2)
C190.070 (3)0.079 (3)0.086 (3)−0.004 (2)0.016 (2)0.009 (3)
C200.077 (3)0.081 (3)0.113 (4)−0.015 (3)0.018 (3)−0.010 (3)
C210.046 (2)0.066 (3)0.063 (2)0.002 (2)0.0094 (19)0.002 (2)
C220.0417 (19)0.062 (2)0.054 (2)−0.0021 (18)0.0065 (16)0.007 (2)
C230.0374 (19)0.081 (3)0.069 (2)−0.0005 (19)0.0063 (17)−0.001 (2)
C240.043 (2)0.082 (3)0.069 (3)−0.003 (2)−0.0026 (17)−0.003 (2)
C250.041 (2)0.064 (3)0.059 (2)0.0010 (18)0.0039 (17)0.003 (2)
C260.042 (2)0.082 (3)0.070 (3)0.007 (2)0.0102 (18)−0.007 (2)
C270.0359 (19)0.087 (3)0.081 (3)0.0007 (19)0.0022 (18)−0.012 (2)
C280.066 (3)0.087 (3)0.103 (3)0.012 (2)0.015 (2)−0.021 (3)

Geometric parameters (Å, °)

O1—C71.355 (5)C10—H10A0.9300
O1—C41.381 (4)C11—C121.385 (5)
O2—C71.195 (4)C12—C131.367 (5)
O3—C111.372 (4)C12—H12A0.9300
O3—C141.411 (4)C13—H13A0.9300
O4—C211.366 (4)C14—H14A0.9600
O4—C181.403 (4)C14—H14B0.9600
O5—C211.203 (4)C14—H14C0.9600
O6—C251.371 (4)C15—C201.349 (6)
O6—C281.414 (4)C15—C161.358 (6)
N1—C71.332 (5)C15—H15A0.9300
N1—C81.418 (5)C16—C171.371 (6)
N1—H1A0.8600C16—H16A0.9300
N2—C211.335 (4)C17—C181.362 (5)
N2—C221.414 (4)C17—H17A0.9300
N2—H2B0.8600C18—C191.359 (5)
C1—C61.279 (6)C19—C201.369 (6)
C1—C21.445 (4)C19—H19A0.9300
C1—H1B0.9300C20—H20A0.9300
C2—C31.371 (7)C22—C271.376 (5)
C2—H2A0.9300C22—C231.378 (5)
C3—C41.344 (5)C23—C241.368 (5)
C3—H3A0.9300C23—H23A0.9300
C4—C51.383 (5)C24—C251.382 (5)
C5—C61.337 (6)C24—H24A0.9300
C5—H5A0.9300C25—C261.357 (5)
C6—H6A0.9300C26—C271.380 (5)
C8—C91.374 (5)C26—H26A0.9300
C8—C131.382 (5)C27—H27A0.9300
C9—C101.374 (5)C28—H28A0.9600
C9—H9A0.9300C28—H28B0.9600
C10—C111.372 (5)C28—H28C0.9600
C7—O1—C4120.3 (3)O3—C14—H14B109.5
C11—O3—C14118.0 (3)H14A—C14—H14B109.5
C21—O4—C18116.4 (3)O3—C14—H14C109.5
C25—O6—C28117.2 (3)H14A—C14—H14C109.5
C7—N1—C8125.9 (3)H14B—C14—H14C109.5
C7—N1—H1A117.0C20—C15—C16120.0 (5)
C8—N1—H1A117.0C20—C15—H15A120.0
C21—N2—C22126.9 (3)C16—C15—H15A120.0
C21—N2—H2B116.6C15—C16—C17120.6 (5)
C22—N2—H2B116.6C15—C16—H16A119.7
C6—C1—C2119.2 (5)C17—C16—H16A119.7
C6—C1—H1B120.4C18—C17—C16118.7 (4)
C2—C1—H1B120.4C18—C17—H17A120.6
C3—C2—C1117.2 (5)C16—C17—H17A120.6
C3—C2—H2A121.4C19—C18—C17121.0 (4)
C1—C2—H2A121.4C19—C18—O4120.1 (4)
C4—C3—C2120.8 (5)C17—C18—O4118.8 (4)
C4—C3—H3A119.6C18—C19—C20119.3 (4)
C2—C3—H3A119.6C18—C19—H19A120.3
C3—C4—O1120.5 (4)C20—C19—H19A120.3
C3—C4—C5119.9 (4)C15—C20—C19120.4 (5)
O1—C4—C5119.3 (4)C15—C20—H20A119.8
C6—C5—C4118.9 (4)C19—C20—H20A119.8
C6—C5—H5A120.5O5—C21—N2128.2 (4)
C4—C5—H5A120.5O5—C21—O4122.9 (3)
C1—C6—C5123.9 (5)N2—C21—O4108.9 (3)
C1—C6—H6A118.1C27—C22—C23117.9 (4)
C5—C6—H6A118.1C27—C22—N2124.4 (3)
O2—C7—N1127.8 (4)C23—C22—N2117.7 (3)
O2—C7—O1123.0 (4)C24—C23—C22120.8 (3)
N1—C7—O1109.2 (3)C24—C23—H23A119.6
C9—C8—C13118.8 (4)C22—C23—H23A119.6
C9—C8—N1122.3 (4)C23—C24—C25121.1 (3)
C13—C8—N1118.8 (3)C23—C24—H24A119.5
C8—C9—C10120.6 (4)C25—C24—H24A119.5
C8—C9—H9A119.7C26—C25—O6125.2 (3)
C10—C9—H9A119.7C26—C25—C24118.3 (4)
C11—C10—C9120.6 (4)O6—C25—C24116.4 (3)
C11—C10—H10A119.7C25—C26—C27121.0 (3)
C9—C10—H10A119.7C25—C26—H26A119.5
O3—C11—C10125.3 (4)C27—C26—H26A119.5
O3—C11—C12115.7 (4)C22—C27—C26120.9 (3)
C10—C11—C12118.9 (4)C22—C27—H27A119.5
C13—C12—C11120.4 (4)C26—C27—H27A119.5
C13—C12—H12A119.8O6—C28—H28A109.5
C11—C12—H12A119.8O6—C28—H28B109.5
C12—C13—C8120.6 (4)H28A—C28—H28B109.5
C12—C13—H13A119.7O6—C28—H28C109.5
C8—C13—H13A119.7H28A—C28—H28C109.5
O3—C14—H14A109.5H28B—C28—H28C109.5
C6—C1—C2—C32.7 (8)C20—C15—C16—C170.2 (7)
C1—C2—C3—C4−0.7 (7)C15—C16—C17—C180.0 (6)
C2—C3—C4—O1173.6 (4)C16—C17—C18—C19−0.3 (6)
C2—C3—C4—C5−0.9 (7)C16—C17—C18—O4176.2 (3)
C7—O1—C4—C3106.2 (5)C21—O4—C18—C19−91.7 (4)
C7—O1—C4—C5−79.3 (5)C21—O4—C18—C1791.7 (4)
C3—C4—C5—C60.5 (6)C17—C18—C19—C200.4 (6)
O1—C4—C5—C6−174.0 (3)O4—C18—C19—C20−176.0 (3)
C2—C1—C6—C5−3.3 (7)C16—C15—C20—C19−0.1 (7)
C4—C5—C6—C11.7 (7)C18—C19—C20—C15−0.2 (6)
C8—N1—C7—O20.3 (8)C22—N2—C21—O5−4.3 (6)
C8—N1—C7—O1179.2 (3)C22—N2—C21—O4175.8 (3)
C4—O1—C7—O2−0.4 (7)C18—O4—C21—O54.5 (6)
C4—O1—C7—N1−179.4 (4)C18—O4—C21—N2−175.5 (3)
C7—N1—C8—C9−34.6 (6)C21—N2—C22—C27−5.7 (6)
C7—N1—C8—C13145.2 (4)C21—N2—C22—C23174.9 (3)
C13—C8—C9—C10−0.8 (6)C27—C22—C23—C24−0.8 (5)
N1—C8—C9—C10179.0 (3)N2—C22—C23—C24178.6 (3)
C8—C9—C10—C110.5 (6)C22—C23—C24—C25−0.7 (6)
C14—O3—C11—C10−5.6 (5)C28—O6—C25—C26−18.3 (5)
C14—O3—C11—C12171.3 (3)C28—O6—C25—C24165.1 (3)
C9—C10—C11—O3177.2 (3)C23—C24—C25—C261.7 (6)
C9—C10—C11—C120.3 (6)C23—C24—C25—O6178.6 (3)
O3—C11—C12—C13−177.8 (3)O6—C25—C26—C27−177.9 (3)
C10—C11—C12—C13−0.7 (6)C24—C25—C26—C27−1.3 (6)
C11—C12—C13—C80.3 (6)C23—C22—C27—C261.2 (5)
C9—C8—C13—C120.4 (6)N2—C22—C27—C26−178.1 (3)
N1—C8—C13—C12−179.3 (3)C25—C26—C27—C22−0.2 (6)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N1—H1A···O50.862.193.038 (4)170
N2—H2B···O2i0.862.223.062 (4)166
C6—H6A···O5ii0.932.583.435 (5)153
C9—H9A···O20.932.522.967 (5)110
C23—H23A···O2i0.932.603.390 (4)144
C27—H27A···O50.932.302.907 (5)122

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HK2744).

References

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