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In the title compound, C
14H
13NO
3, 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
CCDC reference: 217474
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (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
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.
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.
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)..
N-phenyl-
o-methoxybenzohydroxamic acid
top
Crystal data top
C14H13NO3 | F(000) = 1024 |
Mr = 243.25 | Dx = 1.312 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
a = 22.451 (3) Å | Cell parameters from 2709 reflections |
b = 8.3709 (13) Å | θ = 2.1–27.5° |
c = 14.921 (2) Å | µ = 0.09 mm−1 |
β = 118.531 (3)° | T = 293 K |
V = 2463.6 (6) Å3 | Block, colourless |
Z = 8 | 0.50 × 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 tube | Rint = 0.033 |
Graphite monochromator | θmax = 27.5°, θmin = 2.1° |
Detector resolution: 83.66 pixels mm-1 | h = −29→28 |
ω scans | k = −10→9 |
8106 measured reflections | l = −19→19 |
2839 independent reflections | |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.047 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.130 | H-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 parameters | Δρmax = 0.23 e Å−3 |
0 restraints | Δρmin = −0.13 e Å−3 |
Crystal data top
C14H13NO3 | V = 2463.6 (6) Å3 |
Mr = 243.25 | Z = 8 |
Monoclinic, C2/c | Mo Kα radiation |
a = 22.451 (3) Å | µ = 0.09 mm−1 |
b = 8.3709 (13) Å | T = 293 K |
c = 14.921 (2) Å | 0.50 × 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 reflections | Rint = 0.033 |
2839 independent reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.047 | 0 restraints |
wR(F2) = 0.130 | H-atom parameters constrained |
S = 1.04 | Δρmax = 0.23 e Å−3 |
2839 reflections | Δρmin = −0.13 e Å−3 |
163 parameters | |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O1 | 0.26350 (6) | 0.88494 (14) | 0.12891 (7) | 0.0727 (4) | |
H1A | 0.2451 | 0.8431 | 0.0724 | 0.109* | |
O2 | 0.31734 (5) | 0.65663 (14) | 0.07502 (7) | 0.0606 (3) | |
O3 | 0.45786 (5) | 0.77742 (14) | 0.31765 (8) | 0.0679 (3) | |
N1 | 0.30728 (6) | 0.77572 (14) | 0.20054 (8) | 0.0486 (3) | |
C1 | 0.31973 (7) | 0.68471 (17) | 0.36362 (10) | 0.0490 (3) | |
H1B | 0.3165 | 0.5792 | 0.3422 | 0.059* | |
C2 | 0.32723 (8) | 0.7194 (2) | 0.45915 (11) | 0.0597 (4) | |
H2A | 0.3298 | 0.6369 | 0.5026 | 0.072* | |
C3 | 0.33084 (8) | 0.8751 (2) | 0.49009 (11) | 0.0653 (4) | |
H3A | 0.3358 | 0.8977 | 0.5543 | 0.078* | |
C4 | 0.32725 (7) | 0.9970 (2) | 0.42680 (11) | 0.0616 (4) | |
H4A | 0.3294 | 1.1023 | 0.4480 | 0.074* | |
C5 | 0.32045 (7) | 0.96475 (17) | 0.33104 (11) | 0.0529 (3) | |
H5A | 0.3181 | 1.0478 | 0.2881 | 0.064* | |
C6 | 0.31715 (6) | 0.80803 (16) | 0.30051 (9) | 0.0437 (3) | |
C7 | 0.33543 (6) | 0.66695 (16) | 0.16711 (9) | 0.0453 (3) | |
C8 | 0.38821 (6) | 0.55763 (17) | 0.24190 (9) | 0.0453 (3) | |
C9 | 0.37689 (7) | 0.39490 (19) | 0.23187 (11) | 0.0552 (4) | |
H9A | 0.3352 | 0.3559 | 0.1826 | 0.066* | |
C10 | 0.42684 (9) | 0.2898 (2) | 0.29427 (14) | 0.0684 (4) | |
H10A | 0.4191 | 0.1802 | 0.2877 | 0.082* | |
C11 | 0.48836 (9) | 0.3493 (2) | 0.36647 (13) | 0.0722 (5) | |
H11A | 0.5221 | 0.2786 | 0.4086 | 0.087* | |
C12 | 0.50103 (7) | 0.5099 (2) | 0.37769 (11) | 0.0638 (4) | |
H12A | 0.5430 | 0.5475 | 0.4268 | 0.077* | |
C13 | 0.45093 (7) | 0.61640 (19) | 0.31543 (9) | 0.0506 (3) | |
C14 | 0.52019 (9) | 0.8451 (2) | 0.39225 (15) | 0.0855 (6) | |
H14A | 0.5183 | 0.9592 | 0.3850 | 0.128* | |
H14B | 0.5568 | 0.8043 | 0.3828 | 0.128* | |
H14C | 0.5275 | 0.8174 | 0.4592 | 0.128* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0888 (8) | 0.0716 (7) | 0.0385 (5) | 0.0328 (6) | 0.0149 (5) | 0.0087 (5) |
O2 | 0.0616 (6) | 0.0812 (7) | 0.0329 (5) | 0.0130 (5) | 0.0176 (4) | 0.0033 (4) |
O3 | 0.0464 (6) | 0.0718 (8) | 0.0695 (7) | −0.0063 (5) | 0.0149 (5) | −0.0083 (5) |
N1 | 0.0502 (6) | 0.0547 (7) | 0.0347 (5) | 0.0101 (5) | 0.0154 (5) | 0.0065 (5) |
C1 | 0.0468 (7) | 0.0557 (8) | 0.0441 (7) | −0.0014 (6) | 0.0213 (6) | −0.0010 (6) |
C2 | 0.0601 (9) | 0.0766 (11) | 0.0448 (7) | 0.0012 (7) | 0.0270 (7) | 0.0041 (7) |
C3 | 0.0599 (9) | 0.0905 (12) | 0.0415 (7) | 0.0036 (8) | 0.0211 (7) | −0.0098 (8) |
C4 | 0.0504 (8) | 0.0654 (9) | 0.0540 (8) | 0.0007 (7) | 0.0129 (6) | −0.0177 (7) |
C5 | 0.0456 (7) | 0.0552 (8) | 0.0480 (7) | −0.0008 (6) | 0.0143 (6) | −0.0001 (6) |
C6 | 0.0348 (6) | 0.0550 (8) | 0.0362 (6) | 0.0003 (5) | 0.0128 (5) | −0.0007 (5) |
C7 | 0.0398 (6) | 0.0575 (8) | 0.0341 (6) | −0.0006 (5) | 0.0141 (5) | 0.0009 (5) |
C8 | 0.0411 (6) | 0.0613 (8) | 0.0345 (6) | 0.0052 (5) | 0.0188 (5) | 0.0027 (5) |
C9 | 0.0497 (7) | 0.0635 (9) | 0.0501 (7) | 0.0028 (6) | 0.0221 (6) | 0.0019 (6) |
C10 | 0.0670 (10) | 0.0629 (10) | 0.0756 (10) | 0.0119 (8) | 0.0343 (9) | 0.0151 (8) |
C11 | 0.0574 (9) | 0.0854 (13) | 0.0658 (10) | 0.0233 (8) | 0.0230 (8) | 0.0234 (9) |
C12 | 0.0439 (8) | 0.0914 (12) | 0.0471 (7) | 0.0090 (7) | 0.0145 (6) | 0.0038 (8) |
C13 | 0.0421 (6) | 0.0695 (9) | 0.0397 (6) | 0.0024 (6) | 0.0190 (5) | −0.0009 (6) |
C14 | 0.0601 (10) | 0.0968 (14) | 0.0812 (12) | −0.0163 (9) | 0.0188 (9) | −0.0276 (11) |
Geometric parameters (Å, º) top
O1—N1 | 1.3931 (14) | C5—C6 | 1.3791 (19) |
O1—H1A | 0.8200 | C5—H5A | 0.9300 |
O2—C7 | 1.2359 (15) | C7—C8 | 1.4912 (17) |
O3—C13 | 1.3554 (19) | C8—C9 | 1.381 (2) |
O3—C14 | 1.4251 (19) | C8—C13 | 1.3975 (18) |
N1—C7 | 1.3335 (17) | C9—C10 | 1.379 (2) |
N1—C6 | 1.4252 (16) | C9—H9A | 0.9300 |
C1—C6 | 1.3797 (19) | C10—C11 | 1.377 (3) |
C1—C2 | 1.384 (2) | C10—H10A | 0.9300 |
C1—H1B | 0.9300 | C11—C12 | 1.368 (2) |
C2—C3 | 1.372 (2) | C11—H11A | 0.9300 |
C2—H2A | 0.9300 | C12—C13 | 1.387 (2) |
C3—C4 | 1.367 (2) | C12—H12A | 0.9300 |
C3—H3A | 0.9300 | C14—H14A | 0.9600 |
C4—C5 | 1.389 (2) | C14—H14B | 0.9600 |
C4—H4A | 0.9300 | C14—H14C | 0.9600 |
| | | |
N1—O1—H1A | 109.5 | N1—C7—C8 | 119.23 (11) |
C13—O3—C14 | 118.22 (13) | C9—C8—C13 | 119.78 (12) |
C7—N1—O1 | 116.61 (10) | C9—C8—C7 | 119.01 (11) |
C7—N1—C6 | 131.03 (10) | C13—C8—C7 | 120.94 (13) |
O1—N1—C6 | 112.23 (10) | C10—C9—C8 | 120.55 (14) |
C6—C1—C2 | 119.38 (14) | C10—C9—H9A | 119.7 |
C6—C1—H1B | 120.3 | C8—C9—H9A | 119.7 |
C2—C1—H1B | 120.3 | C11—C10—C9 | 119.05 (17) |
C3—C2—C1 | 120.31 (15) | C11—C10—H10A | 120.5 |
C3—C2—H2A | 119.8 | C9—C10—H10A | 120.5 |
C1—C2—H2A | 119.8 | C12—C11—C10 | 121.59 (15) |
C4—C3—C2 | 120.16 (14) | C12—C11—H11A | 119.2 |
C4—C3—H3A | 119.9 | C10—C11—H11A | 119.2 |
C2—C3—H3A | 119.9 | C11—C12—C13 | 119.67 (15) |
C3—C4—C5 | 120.45 (15) | C11—C12—H12A | 120.2 |
C3—C4—H4A | 119.8 | C13—C12—H12A | 120.2 |
C5—C4—H4A | 119.8 | O3—C13—C12 | 125.16 (13) |
C6—C5—C4 | 119.14 (14) | O3—C13—C8 | 115.47 (12) |
C6—C5—H5A | 120.4 | C12—C13—C8 | 119.35 (15) |
C4—C5—H5A | 120.4 | O3—C14—H14A | 109.5 |
C5—C6—C1 | 120.54 (12) | O3—C14—H14B | 109.5 |
C5—C6—N1 | 118.89 (12) | H14A—C14—H14B | 109.5 |
C1—C6—N1 | 120.48 (12) | O3—C14—H14C | 109.5 |
O2—C7—N1 | 120.05 (12) | H14A—C14—H14C | 109.5 |
O2—C7—C8 | 120.71 (12) | H14B—C14—H14C | 109.5 |
| | | |
C6—C1—C2—C3 | 1.2 (2) | N1—C7—C8—C9 | 120.02 (14) |
C1—C2—C3—C4 | −0.2 (2) | O2—C7—C8—C13 | 114.66 (15) |
C2—C3—C4—C5 | −0.5 (2) | N1—C7—C8—C13 | −65.93 (17) |
C3—C4—C5—C6 | 0.2 (2) | C13—C8—C9—C10 | 0.4 (2) |
C4—C5—C6—C1 | 0.8 (2) | C7—C8—C9—C10 | 174.53 (14) |
C4—C5—C6—N1 | 177.36 (12) | C8—C9—C10—C11 | −0.3 (2) |
C2—C1—C6—C5 | −1.5 (2) | C9—C10—C11—C12 | 0.0 (3) |
C2—C1—C6—N1 | −177.99 (12) | C10—C11—C12—C13 | 0.2 (3) |
C7—N1—C6—C5 | 138.63 (15) | C14—O3—C13—C12 | −2.8 (2) |
O1—N1—C6—C5 | −37.05 (16) | C14—O3—C13—C8 | 178.80 (14) |
C7—N1—C6—C1 | −44.8 (2) | C11—C12—C13—O3 | −178.44 (14) |
O1—N1—C6—C1 | 139.54 (13) | C11—C12—C13—C8 | −0.1 (2) |
O1—N1—C7—O2 | −7.0 (2) | C9—C8—C13—O3 | 178.29 (12) |
C6—N1—C7—O2 | 177.52 (13) | C7—C8—C13—O3 | 4.28 (18) |
O1—N1—C7—C8 | 173.63 (12) | C9—C8—C13—C12 | −0.2 (2) |
C6—N1—C7—C8 | −1.9 (2) | C7—C8—C13—C12 | −174.18 (13) |
O2—C7—C8—C9 | −59.39 (18) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1A···O2i | 0.82 | 1.96 | 2.7200 (14) | 153 |
Symmetry code: (i) −x+1/2, −y+3/2, −z. |
Experimental details
Crystal data |
Chemical formula | C14H13NO3 |
Mr | 243.25 |
Crystal system, space group | Monoclinic, C2/c |
Temperature (K) | 293 |
a, b, c (Å) | 22.451 (3), 8.3709 (13), 14.921 (2) |
β (°) | 118.531 (3) |
V (Å3) | 2463.6 (6) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.50 × 0.32 × 0.25 |
|
Data collection |
Diffractometer | Bruker SMART APEX CCD area-detector diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 8106, 2839, 2229 |
Rint | 0.033 |
(sin θ/λ)max (Å−1) | 0.650 |
|
Refinement |
R[F2 > 2σ(F2)], wR(F2), S | 0.047, 0.130, 1.04 |
No. of reflections | 2839 |
No. of parameters | 163 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.23, −0.13 |
Selected geometric parameters (Å, º) topO1—N1 | 1.3931 (14) | O3—C14 | 1.4251 (19) |
O2—C7 | 1.2359 (15) | N1—C7 | 1.3335 (17) |
O3—C13 | 1.3554 (19) | N1—C6 | 1.4252 (16) |
| | | |
C13—O3—C14 | 118.22 (13) | C7—N1—C6 | 131.03 (10) |
C7—N1—O1 | 116.61 (10) | O1—N1—C6 | 112.23 (10) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1A···O2i | 0.82 | 1.96 | 2.7200 (14) | 153 |
Symmetry code: (i) −x+1/2, −y+3/2, −z. |
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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).