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Acta Crystallogr Sect E Struct Rep Online. 2008 January 1; 64(Pt 1): o251.
Published online 2007 December 12. doi:  10.1107/S1600536807064379
PMCID: PMC2915308

3-Meth­oxy-N-p-tolyl­benzohydroxamic acid

Abstract

Two mol­ecules of the title compound, C15H15NO3, are linked by a pair of O—H(...)Ocarbon­yl hydrogen bonds over a centre of inversion to form a hydrogen-bonded dimer. With respect to the –C(=O)—N(OH)– unit, the methoxy-substituted ring is twisted by 42.2 (1)°, whereas the methyl-substituted ring is twisted by 52.2 (1)°.

Related literature

The parent N-phenyl­benzohydroxamic acid exists in the cis form as well as the common trans form (see Yamasaki et al., 2006 [triangle]). For the synthesis and spectroscopic data of the title compound, see: Agrawal & Tandon (1971 [triangle], 1972 [triangle], 1973 [triangle]).

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Object name is e-64-0o251-scheme1.jpg

Experimental

Crystal data

  • C15H15NO3
  • M r = 257.28
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-0o251-efi1.jpg
  • a = 11.332 (1) Å
  • b = 7.939 (1) Å
  • c = 15.567 (2) Å
  • β = 106.397 (2)°
  • V = 1343.5 (2) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.09 mm−1
  • T = 293 (2) K
  • 0.47 × 0.36 × 0.27 mm

Data collection

  • Bruker APEX diffractometer
  • Absorption correction: none
  • 6832 measured reflections
  • 2378 independent reflections
  • 1748 reflections with I > 2σ(I)
  • R int = 0.023

Refinement

  • R[F 2 > 2σ(F 2)] = 0.044
  • wR(F 2) = 0.121
  • S = 1.06
  • 2378 reflections
  • 178 parameters
  • 1 restraint
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.17 e Å−3
  • Δρmin = −0.13 e Å−3

Data collection: SMART (Bruker, 2000 [triangle]); cell refinement: SAINT (Bruker, 2000 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 [triangle]); molecular graphics: X-SEED (Barbour, 2001 [triangle]); software used to prepare material for publication: publCIF (Westrip, 2007 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536807064379/av2005sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807064379/av2005Isup2.hkl

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

Acknowledgments

The authors acknowledge Professor Bohari M. Yamin’s assistance with the diffraction measurements. The authors thank Universiti Kebangsaan Malaysia and the University of Malaya for supporting this study.

supplementary crystallographic information

Experimental

3-Methoxybenzoyl chloride (1.4 g, 0.01 mmol) dissolved in ether was added to N-(4-tolyl)hydroxylamine (1.0 g, 0.01 mmol) dissolved in ether in the presence of sodium bicarbonate (0.7 g, 0.01 mmol). The reaction was carried out in an ice-bath. The solid that formed on removal of the solvent was extracted with ethyl acetate (10 ml). The solution yielded crystals after being set aside in a refrigerator.

Refinement

The carbon-bound H atoms were placed at calculated positions (C–H 0.93– 0.97 Å), and were included in the refinement in the riding model approximation with U(H) set to 1.2–1.5Ueq(C). The hydropxy hydrogen atom was located in a difference Fouier map, and was refined with a distance restraint of O–H 0.85±0.01 Å.

Figures

Fig. 1.
Thermal ellipsoid plot of two molecules of C15H15NO3. Displacement ellipsoids are drawn at the 50% probability level, and H atoms are shown as spheres of arbitrary radii.

Crystal data

C15H15NO3F000 = 544
Mr = 257.28Dx = 1.272 Mg m3
Monoclinic, P21/cMo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 7258 reflections
a = 11.332 (1) Åθ = 2.8–21.7º
b = 7.939 (1) ŵ = 0.09 mm1
c = 15.567 (2) ÅT = 293 (2) K
β = 106.397 (2)ºIrregular block, colorless
V = 1343.5 (2) Å30.47 × 0.36 × 0.27 mm
Z = 4

Data collection

Bruker APEX diffractometer1748 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.023
Monochromator: Graphiteθmax = 25.1º
T = 293(2) Kθmin = 1.9º
[var phi] and ω scansh = −13→13
Absorption correction: nonek = −9→9
6832 measured reflectionsl = −14→18
2378 independent reflections

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.044H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.121  w = 1/[σ2(Fo2) + (0.0588P)2 + 0.1129P] where P = (Fo2 + 2Fc2)/3
S = 1.06(Δ/σ)max = 0.001
2378 reflectionsΔρmax = 0.17 e Å3
178 parametersΔρmin = −0.13 e Å3
1 restraintExtinction correction: none
Primary atom site location: structure-invariant direct methods

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

xyzUiso*/Ueq
O10.50151 (12)0.30374 (18)0.40770 (9)0.0623 (4)
H10.494 (2)0.390 (2)0.4393 (15)0.108 (9)*
O20.62368 (12)0.42304 (16)0.56320 (8)0.0635 (4)
O30.94373 (12)0.18762 (18)0.82493 (8)0.0681 (4)
N10.60896 (13)0.22480 (18)0.45952 (9)0.0484 (4)
C10.62980 (15)0.0686 (2)0.42159 (11)0.0436 (4)
C20.63120 (16)0.0638 (2)0.33340 (12)0.0521 (5)
H20.61860.16180.29930.063*
C30.65135 (16)−0.0866 (3)0.29608 (13)0.0585 (5)
H30.6524−0.08900.23660.070*
C40.67003 (16)−0.2340 (2)0.34493 (15)0.0588 (5)
C50.66643 (17)−0.2264 (2)0.43301 (15)0.0616 (6)
H50.6788−0.32450.46700.074*
C60.64499 (16)−0.0772 (2)0.47175 (13)0.0532 (5)
H60.6409−0.07510.53060.064*
C70.6942 (2)−0.3978 (3)0.30416 (18)0.0897 (8)
H7A0.6333−0.47910.30820.135*
H7B0.7744−0.43870.33590.135*
H7C0.6904−0.38020.24240.135*
C80.66747 (16)0.2968 (2)0.53701 (11)0.0453 (4)
C90.78932 (15)0.2288 (2)0.58918 (11)0.0429 (4)
C100.88037 (16)0.1831 (2)0.55018 (13)0.0546 (5)
H100.86470.18390.48820.065*
C110.99379 (17)0.1367 (3)0.60382 (14)0.0639 (6)
H111.05480.10600.57750.077*
C121.01962 (17)0.1344 (3)0.69602 (14)0.0606 (5)
H121.09680.10150.73140.073*
C130.92907 (17)0.1818 (2)0.73517 (12)0.0502 (5)
C140.81453 (16)0.2289 (2)0.68151 (12)0.0468 (4)
H140.75370.26100.70770.056*
C151.0630 (2)0.1592 (4)0.88294 (15)0.0953 (9)
H15A1.06060.16570.94400.143*
H15B1.11840.24320.87250.143*
H15C1.09110.04950.87170.143*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.0614 (9)0.0629 (9)0.0531 (8)0.0250 (7)0.0004 (7)−0.0025 (7)
O20.0637 (8)0.0571 (8)0.0624 (8)0.0228 (7)0.0058 (7)−0.0098 (6)
O30.0640 (9)0.0829 (10)0.0491 (8)0.0086 (7)0.0024 (7)0.0036 (7)
N10.0468 (9)0.0480 (9)0.0461 (9)0.0125 (7)0.0061 (7)0.0007 (7)
C10.0391 (9)0.0429 (10)0.0466 (10)0.0025 (7)0.0086 (8)−0.0022 (8)
C20.0516 (11)0.0528 (11)0.0498 (11)0.0051 (8)0.0109 (9)−0.0004 (9)
C30.0513 (11)0.0701 (14)0.0514 (11)0.0044 (10)0.0104 (9)−0.0129 (10)
C40.0418 (10)0.0537 (12)0.0753 (14)−0.0004 (9)0.0076 (10)−0.0191 (10)
C50.0546 (12)0.0439 (11)0.0822 (15)0.0003 (9)0.0123 (11)0.0040 (10)
C60.0535 (11)0.0508 (11)0.0543 (11)0.0023 (9)0.0134 (9)0.0051 (9)
C70.0737 (15)0.0686 (15)0.121 (2)0.0060 (12)0.0177 (14)−0.0378 (14)
C80.0469 (10)0.0425 (10)0.0464 (10)0.0050 (8)0.0129 (9)0.0009 (8)
C90.0425 (9)0.0355 (9)0.0492 (10)0.0021 (7)0.0103 (8)−0.0015 (7)
C100.0479 (11)0.0607 (12)0.0549 (12)0.0027 (9)0.0142 (9)−0.0065 (9)
C110.0469 (11)0.0752 (14)0.0718 (14)0.0071 (10)0.0202 (10)−0.0125 (11)
C120.0430 (10)0.0606 (12)0.0713 (15)0.0075 (9)0.0051 (10)−0.0037 (10)
C130.0520 (11)0.0425 (10)0.0514 (12)0.0008 (8)0.0071 (9)−0.0011 (8)
C140.0434 (10)0.0445 (10)0.0525 (11)0.0043 (8)0.0136 (8)0.0001 (8)
C150.0872 (18)0.118 (2)0.0605 (14)0.0368 (15)−0.0128 (13)−0.0057 (13)

Geometric parameters (Å, °)

O1—N11.4041 (18)C7—H7A0.9600
O1—H10.86 (1)C7—H7B0.9600
O2—C81.238 (2)C7—H7C0.9600
O3—C131.361 (2)C8—C91.491 (2)
O3—C151.416 (2)C9—C101.385 (2)
N1—C81.330 (2)C9—C141.384 (2)
N1—C11.422 (2)C10—C111.371 (3)
C1—C21.378 (2)C10—H100.9300
C1—C61.380 (2)C11—C121.382 (3)
C2—C31.375 (3)C11—H110.9300
C2—H20.9300C12—C131.385 (3)
C3—C41.379 (3)C12—H120.9300
C3—H30.9300C13—C141.382 (2)
C4—C51.385 (3)C14—H140.9300
C4—C71.506 (3)C15—H15A0.9600
C5—C61.381 (3)C15—H15B0.9600
C5—H50.9300C15—H15C0.9600
C6—H60.9300
N1—O1—H1103.5 (18)H7B—C7—H7C109.5
C13—O3—C15117.87 (16)O2—C8—N1120.20 (15)
C8—N1—O1117.30 (14)O2—C8—C9120.62 (15)
C8—N1—C1130.73 (14)N1—C8—C9119.10 (15)
O1—N1—C1111.69 (13)C10—C9—C14119.63 (16)
C2—C1—C6120.42 (16)C10—C9—C8123.08 (16)
C2—C1—N1119.18 (15)C14—C9—C8116.95 (15)
C6—C1—N1120.38 (16)C11—C10—C9119.33 (18)
C3—C2—C1119.64 (17)C11—C10—H10120.3
C3—C2—H2120.2C9—C10—H10120.3
C1—C2—H2120.2C10—C11—C12121.57 (18)
C2—C3—C4121.47 (18)C10—C11—H11119.2
C2—C3—H3119.3C12—C11—H11119.2
C4—C3—H3119.3C11—C12—C13119.17 (18)
C3—C4—C5117.80 (17)C11—C12—H12120.4
C3—C4—C7121.2 (2)C13—C12—H12120.4
C5—C4—C7121.0 (2)O3—C13—C14115.67 (16)
C6—C5—C4121.85 (18)O3—C13—C12124.76 (17)
C6—C5—H5119.1C14—C13—C12119.57 (17)
C4—C5—H5119.1C13—C14—C9120.72 (16)
C1—C6—C5118.78 (18)C13—C14—H14119.6
C1—C6—H6120.6C9—C14—H14119.6
C5—C6—H6120.6O3—C15—H15A109.5
C4—C7—H7A109.5O3—C15—H15B109.5
C4—C7—H7B109.5H15A—C15—H15B109.5
H7A—C7—H7B109.5O3—C15—H15C109.5
C4—C7—H7C109.5H15A—C15—H15C109.5
H7A—C7—H7C109.5H15B—C15—H15C109.5
C8—N1—C1—C2−133.3 (2)C1—N1—C8—C913.6 (3)
O1—N1—C1—C253.0 (2)O2—C8—C9—C10−133.46 (18)
C8—N1—C1—C648.5 (3)N1—C8—C9—C1043.3 (2)
O1—N1—C1—C6−125.21 (17)O2—C8—C9—C1439.8 (2)
C6—C1—C2—C3−1.8 (3)N1—C8—C9—C14−143.42 (16)
N1—C1—C2—C3179.96 (15)C14—C9—C10—C110.8 (3)
C1—C2—C3—C40.2 (3)C8—C9—C10—C11173.91 (18)
C2—C3—C4—C50.8 (3)C9—C10—C11—C120.0 (3)
C2—C3—C4—C7−178.94 (18)C10—C11—C12—C13−0.7 (3)
C3—C4—C5—C60.0 (3)C15—O3—C13—C14−172.98 (19)
C7—C4—C5—C6179.68 (18)C15—O3—C13—C126.5 (3)
C2—C1—C6—C52.5 (3)C11—C12—C13—O3−178.85 (18)
N1—C1—C6—C5−179.29 (15)C11—C12—C13—C140.6 (3)
C4—C5—C6—C1−1.6 (3)O3—C13—C14—C9179.64 (15)
O1—N1—C8—O23.7 (3)C12—C13—C14—C90.1 (3)
C1—N1—C8—O2−169.65 (16)C10—C9—C14—C13−0.8 (2)
O1—N1—C8—C9−173.02 (14)C8—C9—C14—C13−174.38 (15)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O1—H1···O2i0.86 (1)1.99 (2)2.699 (2)139 (2)

Symmetry codes: (i) −x+1, −y+1, −z+1.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: AV2005).

References

  • Agrawal, Y. K. & Tandon, S. G. (1971). J. Chem. Eng. Data, 16, 495–506.
  • Agrawal, Y. K. & Tandon, S. G. (1972). J. Indian Chem. Soc.49, 911–914.
  • Agrawal, Y. K. & Tandon, S. G. (1973). Spectrosc. Lett.6, 547–562.
  • Barbour, L. J. (2001). J. Supramol. Chem.1, 189–191.
  • Bruker (2000). SMART (Version 5.63A) and SAINT (Version 6.63A). Bruker AXS Inc., Madison, Wisconsin, USA.
  • Sheldrick, G. M. (1997). SHELXS97 and SHELXL97 University of Göttingen, Germany.
  • Westrip, S. P. (2007). publCIF In preparation.
  • Yamasaki, R., Tanatani, A., Azumaya, I., Masu, H., Yamaguchi, K. & Kagechika, H. (2006). Cryst. Growth Des.6, 2007–2010.

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