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In the title compound, C14H13NO3, the phenyl ring is cis to the methoxy­phenyl group across the C—N bond. The crystal structure is stabilized by weak intermolecular O—H...O interactions, forming dimers that are arranged in layers parallel to the ab face.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803013564/ac6044sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803013564/ac6044Isup2.hkl
Contains datablock I

CCDC reference: 217474

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.047
  • wR factor = 0.130
  • Data-to-parameter ratio = 17.4

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry








Comment top

Interest on hydroaxamic acid derivatives is not only on its complexation with metals and as a technique for the separation of rare earth metals in particular (Kapoor et al., 1975), but also the fact that it has numerous biological and medical applications.

The title compound, (I), is discrete and has a cis configuration with respect to the positions of phenyl and methoxyphenyl groups about the C7—N2 bond. The bond lengths and angles are in normal ranges (Allen et al., 1987). The phenyl (C1–C6), methoxyphenyl (O3/C8–C14) [maximum deviation at O3 of 0.018 (1) Å from the mean plane] and O1/O2/N1/C6 fragments are planar. The central O1/O2/N1/C6 fragment makes dihedral angles with the phenyl and methoxyphenyl groups of 39.87 (8) and 63.75 (7)°, respectively. The phenyl and the methoxyphenyl groups are inclined at 64.53 (7) Å with respect to one another. In the crystal structure, the molecules are linked by intermolecular hydrogen bonding, O1—H1A···O2 (the symmetry code is as in Table 2) to form dimers and are arranged parallel to ab face (Fig.2).

Experimental top

An ether solution of o-methoxybenzoyl chloride (8.6 g, 50 mmol) was added dropwise to a stirred cold ethereal solution of N-phenylhydroxylamine (5.45 g, 50 mmol) containing sodium hydrogen carbonate (4.2 g, 50 mmol). The precipitate was filtered and washed with cold ethanol. Some good quality crystals suitable for X-ray analysis were obained by recrystallization from ethyl acetate.

Refinement top

After their location in the difference Fourier map, all H atoms were included in the refinement in geometrically calculated positions, and allowed to ride on the parent C or O atoms, with C—H = 0.93–0.97 Å and O—H = 0.82 Å.

Computing details top

Data collection: SMART (Seimens, 1996); cell refinement: SAINT (Seimens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL (Sheldrick, 1997); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 1990)..

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound, (I), with 50% probability displacement ellipsoids.
[Figure 2] Fig. 2. Packing diagram of compound (I), viewed down the c axis. The dashed lines denote the O—H···O hydrogen bond.
N-phenyl-o-methoxybenzohydroxamic acid top
Crystal data top
C14H13NO3F(000) = 1024
Mr = 243.25Dx = 1.312 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
a = 22.451 (3) ÅCell parameters from 2709 reflections
b = 8.3709 (13) Åθ = 2.1–27.5°
c = 14.921 (2) ŵ = 0.09 mm1
β = 118.531 (3)°T = 293 K
V = 2463.6 (6) Å3Block, colourless
Z = 80.50 × 0.32 × 0.25 mm
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
2229 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.033
Graphite monochromatorθmax = 27.5°, θmin = 2.1°
Detector resolution: 83.66 pixels mm-1h = 2928
ω scansk = 109
8106 measured reflectionsl = 1919
2839 independent reflections
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)] = 0.047Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.130H-atom parameters constrained
S = 1.04 w = 1/[σ2(Fo2) + (0.0593P)2 + 0.5626P]
where P = (Fo2 + 2Fc2)/3
2839 reflections(Δ/σ)max < 0.001
163 parametersΔρmax = 0.23 e Å3
0 restraintsΔρmin = 0.13 e Å3
Crystal data top
C14H13NO3V = 2463.6 (6) Å3
Mr = 243.25Z = 8
Monoclinic, C2/cMo Kα radiation
a = 22.451 (3) ŵ = 0.09 mm1
b = 8.3709 (13) ÅT = 293 K
c = 14.921 (2) Å0.50 × 0.32 × 0.25 mm
β = 118.531 (3)°
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
2229 reflections with I > 2σ(I)
8106 measured reflectionsRint = 0.033
2839 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0470 restraints
wR(F2) = 0.130H-atom parameters constrained
S = 1.04Δρmax = 0.23 e Å3
2839 reflectionsΔρmin = 0.13 e Å3
163 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.26350 (6)0.88494 (14)0.12891 (7)0.0727 (4)
H1A0.24510.84310.07240.109*
O20.31734 (5)0.65663 (14)0.07502 (7)0.0606 (3)
O30.45786 (5)0.77742 (14)0.31765 (8)0.0679 (3)
N10.30728 (6)0.77572 (14)0.20054 (8)0.0486 (3)
C10.31973 (7)0.68471 (17)0.36362 (10)0.0490 (3)
H1B0.31650.57920.34220.059*
C20.32723 (8)0.7194 (2)0.45915 (11)0.0597 (4)
H2A0.32980.63690.50260.072*
C30.33084 (8)0.8751 (2)0.49009 (11)0.0653 (4)
H3A0.33580.89770.55430.078*
C40.32725 (7)0.9970 (2)0.42680 (11)0.0616 (4)
H4A0.32941.10230.44800.074*
C50.32045 (7)0.96475 (17)0.33104 (11)0.0529 (3)
H5A0.31811.04780.28810.064*
C60.31715 (6)0.80803 (16)0.30051 (9)0.0437 (3)
C70.33543 (6)0.66695 (16)0.16711 (9)0.0453 (3)
C80.38821 (6)0.55763 (17)0.24190 (9)0.0453 (3)
C90.37689 (7)0.39490 (19)0.23187 (11)0.0552 (4)
H9A0.33520.35590.18260.066*
C100.42684 (9)0.2898 (2)0.29427 (14)0.0684 (4)
H10A0.41910.18020.28770.082*
C110.48836 (9)0.3493 (2)0.36647 (13)0.0722 (5)
H11A0.52210.27860.40860.087*
C120.50103 (7)0.5099 (2)0.37769 (11)0.0638 (4)
H12A0.54300.54750.42680.077*
C130.45093 (7)0.61640 (19)0.31543 (9)0.0506 (3)
C140.52019 (9)0.8451 (2)0.39225 (15)0.0855 (6)
H14A0.51830.95920.38500.128*
H14B0.55680.80430.38280.128*
H14C0.52750.81740.45920.128*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0888 (8)0.0716 (7)0.0385 (5)0.0328 (6)0.0149 (5)0.0087 (5)
O20.0616 (6)0.0812 (7)0.0329 (5)0.0130 (5)0.0176 (4)0.0033 (4)
O30.0464 (6)0.0718 (8)0.0695 (7)0.0063 (5)0.0149 (5)0.0083 (5)
N10.0502 (6)0.0547 (7)0.0347 (5)0.0101 (5)0.0154 (5)0.0065 (5)
C10.0468 (7)0.0557 (8)0.0441 (7)0.0014 (6)0.0213 (6)0.0010 (6)
C20.0601 (9)0.0766 (11)0.0448 (7)0.0012 (7)0.0270 (7)0.0041 (7)
C30.0599 (9)0.0905 (12)0.0415 (7)0.0036 (8)0.0211 (7)0.0098 (8)
C40.0504 (8)0.0654 (9)0.0540 (8)0.0007 (7)0.0129 (6)0.0177 (7)
C50.0456 (7)0.0552 (8)0.0480 (7)0.0008 (6)0.0143 (6)0.0001 (6)
C60.0348 (6)0.0550 (8)0.0362 (6)0.0003 (5)0.0128 (5)0.0007 (5)
C70.0398 (6)0.0575 (8)0.0341 (6)0.0006 (5)0.0141 (5)0.0009 (5)
C80.0411 (6)0.0613 (8)0.0345 (6)0.0052 (5)0.0188 (5)0.0027 (5)
C90.0497 (7)0.0635 (9)0.0501 (7)0.0028 (6)0.0221 (6)0.0019 (6)
C100.0670 (10)0.0629 (10)0.0756 (10)0.0119 (8)0.0343 (9)0.0151 (8)
C110.0574 (9)0.0854 (13)0.0658 (10)0.0233 (8)0.0230 (8)0.0234 (9)
C120.0439 (8)0.0914 (12)0.0471 (7)0.0090 (7)0.0145 (6)0.0038 (8)
C130.0421 (6)0.0695 (9)0.0397 (6)0.0024 (6)0.0190 (5)0.0009 (6)
C140.0601 (10)0.0968 (14)0.0812 (12)0.0163 (9)0.0188 (9)0.0276 (11)
Geometric parameters (Å, º) top
O1—N11.3931 (14)C5—C61.3791 (19)
O1—H1A0.8200C5—H5A0.9300
O2—C71.2359 (15)C7—C81.4912 (17)
O3—C131.3554 (19)C8—C91.381 (2)
O3—C141.4251 (19)C8—C131.3975 (18)
N1—C71.3335 (17)C9—C101.379 (2)
N1—C61.4252 (16)C9—H9A0.9300
C1—C61.3797 (19)C10—C111.377 (3)
C1—C21.384 (2)C10—H10A0.9300
C1—H1B0.9300C11—C121.368 (2)
C2—C31.372 (2)C11—H11A0.9300
C2—H2A0.9300C12—C131.387 (2)
C3—C41.367 (2)C12—H12A0.9300
C3—H3A0.9300C14—H14A0.9600
C4—C51.389 (2)C14—H14B0.9600
C4—H4A0.9300C14—H14C0.9600
N1—O1—H1A109.5N1—C7—C8119.23 (11)
C13—O3—C14118.22 (13)C9—C8—C13119.78 (12)
C7—N1—O1116.61 (10)C9—C8—C7119.01 (11)
C7—N1—C6131.03 (10)C13—C8—C7120.94 (13)
O1—N1—C6112.23 (10)C10—C9—C8120.55 (14)
C6—C1—C2119.38 (14)C10—C9—H9A119.7
C6—C1—H1B120.3C8—C9—H9A119.7
C2—C1—H1B120.3C11—C10—C9119.05 (17)
C3—C2—C1120.31 (15)C11—C10—H10A120.5
C3—C2—H2A119.8C9—C10—H10A120.5
C1—C2—H2A119.8C12—C11—C10121.59 (15)
C4—C3—C2120.16 (14)C12—C11—H11A119.2
C4—C3—H3A119.9C10—C11—H11A119.2
C2—C3—H3A119.9C11—C12—C13119.67 (15)
C3—C4—C5120.45 (15)C11—C12—H12A120.2
C3—C4—H4A119.8C13—C12—H12A120.2
C5—C4—H4A119.8O3—C13—C12125.16 (13)
C6—C5—C4119.14 (14)O3—C13—C8115.47 (12)
C6—C5—H5A120.4C12—C13—C8119.35 (15)
C4—C5—H5A120.4O3—C14—H14A109.5
C5—C6—C1120.54 (12)O3—C14—H14B109.5
C5—C6—N1118.89 (12)H14A—C14—H14B109.5
C1—C6—N1120.48 (12)O3—C14—H14C109.5
O2—C7—N1120.05 (12)H14A—C14—H14C109.5
O2—C7—C8120.71 (12)H14B—C14—H14C109.5
C6—C1—C2—C31.2 (2)N1—C7—C8—C9120.02 (14)
C1—C2—C3—C40.2 (2)O2—C7—C8—C13114.66 (15)
C2—C3—C4—C50.5 (2)N1—C7—C8—C1365.93 (17)
C3—C4—C5—C60.2 (2)C13—C8—C9—C100.4 (2)
C4—C5—C6—C10.8 (2)C7—C8—C9—C10174.53 (14)
C4—C5—C6—N1177.36 (12)C8—C9—C10—C110.3 (2)
C2—C1—C6—C51.5 (2)C9—C10—C11—C120.0 (3)
C2—C1—C6—N1177.99 (12)C10—C11—C12—C130.2 (3)
C7—N1—C6—C5138.63 (15)C14—O3—C13—C122.8 (2)
O1—N1—C6—C537.05 (16)C14—O3—C13—C8178.80 (14)
C7—N1—C6—C144.8 (2)C11—C12—C13—O3178.44 (14)
O1—N1—C6—C1139.54 (13)C11—C12—C13—C80.1 (2)
O1—N1—C7—O27.0 (2)C9—C8—C13—O3178.29 (12)
C6—N1—C7—O2177.52 (13)C7—C8—C13—O34.28 (18)
O1—N1—C7—C8173.63 (12)C9—C8—C13—C120.2 (2)
C6—N1—C7—C81.9 (2)C7—C8—C13—C12174.18 (13)
O2—C7—C8—C959.39 (18)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1A···O2i0.821.962.7200 (14)153
Symmetry code: (i) x+1/2, y+3/2, z.

Experimental details

Crystal data
Chemical formulaC14H13NO3
Mr243.25
Crystal system, space groupMonoclinic, C2/c
Temperature (K)293
a, b, c (Å)22.451 (3), 8.3709 (13), 14.921 (2)
β (°) 118.531 (3)
V3)2463.6 (6)
Z8
Radiation typeMo Kα
µ (mm1)0.09
Crystal size (mm)0.50 × 0.32 × 0.25
Data collection
DiffractometerBruker SMART APEX CCD area-detector
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
8106, 2839, 2229
Rint0.033
(sin θ/λ)max1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.047, 0.130, 1.04
No. of reflections2839
No. of parameters163
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.23, 0.13

Computer programs: SMART (Seimens, 1996), SAINT (Seimens, 1996), SAINT, SHELXTL (Sheldrick, 1997), SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 1990)..

Selected geometric parameters (Å, º) top
O1—N11.3931 (14)O3—C141.4251 (19)
O2—C71.2359 (15)N1—C71.3335 (17)
O3—C131.3554 (19)N1—C61.4252 (16)
C13—O3—C14118.22 (13)C7—N1—C6131.03 (10)
C7—N1—O1116.61 (10)O1—N1—C6112.23 (10)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1A···O2i0.821.962.7200 (14)153
Symmetry code: (i) x+1/2, y+3/2, z.
 

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