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The structure of the title compound, C15H12N2O4, consists of a polymeric arrangement, around inversion centres, of mol­ecules linked through O—H...N and O—H...O hydrogen bonds; there are also intramolecular hydrogen bonds. All these hydrogen-bond interactions result in the formation of infinite chains parallel to the [010] direction. The oxime group has an E conformation.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270104003890/gd1303sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270104003890/gd1303Isup2.hkl
Contains datablock I

CCDC reference: 237941

Comment top

In general, oximes and their derivatives are very important compounds for the chemical industry and in medicine, due to their biological activity. Experimental studies on derivatives of oxime groups have been performed by many researchers (Bertolasi et al., 1982; Gilli et al., 1983; Hökelek Zülfikaroglu & Batı, 2001). Oximes have various insecticidal, miticidal and nematodicidal activities and are employed as antidotes against organophosphorus poisons. Carbonyloximes are employed in the separation and spectrophotometric determination of Ni, Pd, Co, Fe and Cu metals. Besides these properties, the oxime (CN—OH) group possesses stronger hydrogen-bonding capabilities than alcohols, phenols and carboxylic acids (Marsman et al., 1999). Hydrogen bonding plays a key role in molecular recognition in chemical engineering (Bertolasi et al., 1982; Gilli et al., 1983; Hökelek Batı et al., 2001). Intermolecular hydrogen bonding has received considerable attention among directional noncovalent intermolecular interactions (Etter et al., 1990), which combine moderate strength and directionality in designing compounds to form supramolecular structures (Karle et al., 1996). There were two Hökelek et al., 2001 references in the original CIF, with no distinction made. Please check they have been correctly cited in this paragraph and below.

The crystal structure determination of the title compound, (I), was carried out to determine the strength of the hydrogen-bonding capabilities of the oxime group, as well as to establish the molecular arrangement, and also to compare the geometry of the oxime moiety with those found in N-(3-chloro-4-methoxyphenyl)-N'-hydroxy-2-oxo-2-phenylacetamidine, (II) (Soylu et al., 2003), 1-(2,6-dimethylphenylamino)propane-1,2-dione dioxime, (III) (Hökelek Zülfikaroglu & Batı, 2001) and N-(3,4-dichlorophenyl)-N'-hydroxy-2-oxo-2-phenylacetamidine, (IV) (Hökelek et al., 2003). \sch

Compound (I) (Fig.1) consists of two aromatic groups linked through a monoxime group. The dihedral angles between the oxime plane A (O1/N1/C7) and rings B (C1—C6) and C (C9—C14) are A/B = 58.61 (10), A/C = 30.13 (11) and B/C = 75.30 (9)° (with approximate s.u.s). Rings B and C are nearly perpendicular to each other. Ring B is linked to the CN—OH group by atom C2(O2). The other ring, C, is linked to the same functional group by atom N2(H2). The steric effects of the substituents bonded to the C atom of the oxime group may influence the bond lengths and angles of the oxime moiety.

A comparison of the bond lengths and angles in compounds (I)-(IV) (Table 2) shows significant changes in the geometry of the oxime moiety. The CN and C—C bond lengths and CN—O bond angles in (I) and (II) are larger than the corresponding values reported in (III), and smaller than those in (IV). The O—N and C—CN values in (I) and (II) are smaller than those found in (III) and (IV). The bond lengths and angles of the oxime moiety in (I) are in accord with the reported values for (II). The differences reported here may be partly due to the steric effect of the 2-carboxyl group.

The oxime moiety in (I) has an E configuration, with C2—C1—N1—O1 169.11 (14)°, which is slightly different from the torsion angles found in related studies (Soylu et al., 2003; Hökelek Zülfikaroglu & Batı, 2001). In this configuration, atom O1 of the oxime group and atom O3 of the carboxyl group behave as donors in intermolecular hydrogen bonds around the inversion centre [O1···N1i 2.780 (2) and O3···O4ii 2.644 (3) Å; symmetry codes: (i) 1 − x, 1 − y, 1 − z; (ii) 1 − x, −y, 1 − z; Fig. 2]. There are also intramolecular N···O hydrogen bonds in the molecule [N2···O1 2.548 (2) and N2···O4 2.667 (2) Å; Table 1].

All the above-mentioned inter- and intramolecular hydrogen bonds in (I) are highly effective in forming polymeric chains, thereby stabilizing the crystal structure. As can be seen from the packing diagram (Fig. 2), the chains are approximately parallel to the b axis. Dipole-dipole and van der Waals interactions are also effective in the molecular packing in the crystal structure.

Experimental top

A solution of anthranilic acid (2.06 g, 0.015 mol) in dichloromethane (20 ml) was added dropwise to a solution of ω-chloroisonitrosoacetophenone (2.75 g, 0.015 mol) in Solvent? (Volume?). The precipated product was filtered off and the resulting solution was allowed to stand for 1 h at room temperature for crystallizarion to occur.

Refinement top

H atoms on N and O atoms were located from a difference Fourier map and freely refined, giving an N—H distance of 0.86 (2) Å, and O—H distances of 0.96 (3) and 1.02 (3) Å. H atoms bonded to C atoms were treated as riding, with a C—H distance of 0.93 Å.

Computing details top

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top
[Figure 1] Fig. 1. A view of the molecule of (I), with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level and H atoms are shown as small spheres of arbitrary radii.
[Figure 2] Fig. 2. A diagram showing the hydrogen-bonding interactions in (I) [symmetry codes: (i) 1 − x, 1 − y, 1 − z; (ii) 1 − x, −y, 1 − z.]
2-[Benzoyl(hydroxyimino)methylamino]benzoic acid top
Crystal data top
C15H12N2O4F(000) = 1184
Mr = 284.27Dx = 1.351 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 4812 reflections
a = 20.6850 (19) Åθ = 1.8–27.7°
b = 13.1680 (13) ŵ = 0.10 mm1
c = 10.488 (11) ÅT = 293 K
β = 101.921 (5)°Prism, colourless
V = 2795 (3) Å30.40 × 0.27 × 0.16 mm
Z = 8
Data collection top
Stoe IPDS 2
diffractometer
1472 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.088
Graphite monochromatorθmax = 25.0°, θmin = 1.9°
Detector resolution: 6.67 pixels mm-1h = 2424
ϕ scansk = 1515
12250 measured reflectionsl = 1212
2477 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)] = 0.041Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.097H atoms treated by a mixture of independent and constrained refinement
S = 0.86 w = 1/[σ2(Fo2) + (0.0573P)2]
where P = (Fo2 + 2Fc2)/3
2477 reflections(Δ/σ)max < 0.001
202 parametersΔρmax = 0.22 e Å3
0 restraintsΔρmin = 0.22 e Å3
Crystal data top
C15H12N2O4V = 2795 (3) Å3
Mr = 284.27Z = 8
Monoclinic, C2/cMo Kα radiation
a = 20.6850 (19) ŵ = 0.10 mm1
b = 13.1680 (13) ÅT = 293 K
c = 10.488 (11) Å0.40 × 0.27 × 0.16 mm
β = 101.921 (5)°
Data collection top
Stoe IPDS 2
diffractometer
1472 reflections with I > 2σ(I)
12250 measured reflectionsRint = 0.088
2477 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0410 restraints
wR(F2) = 0.097H atoms treated by a mixture of independent and constrained refinement
S = 0.86Δρmax = 0.22 e Å3
2477 reflectionsΔρmin = 0.22 e Å3
202 parameters
Special details top

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) top
xyzUiso*/Ueq
N10.45858 (7)0.43672 (10)0.40083 (14)0.0595 (4)
N20.42740 (8)0.27811 (11)0.31062 (16)0.0631 (4)
O10.51493 (6)0.38195 (9)0.46255 (14)0.0734 (4)
O20.30225 (7)0.38083 (11)0.28185 (17)0.0902 (5)
O30.44468 (9)0.03770 (9)0.35035 (16)0.0849 (5)
O40.47357 (7)0.11120 (9)0.44267 (14)0.0778 (4)
C30.34780 (9)0.53547 (12)0.23034 (16)0.0545 (4)
C40.28888 (10)0.58714 (16)0.2243 (2)0.0746 (6)
H40.25410.55560.25240.089*
C50.28168 (15)0.6836 (2)0.1776 (3)0.1024 (9)
H50.24200.71780.17380.123*
C60.33225 (18)0.73047 (17)0.1363 (3)0.1061 (10)
H60.32670.79650.10430.127*
C70.39127 (14)0.68161 (17)0.1412 (2)0.0911 (7)
H70.42580.71440.11380.109*
C80.39892 (10)0.58254 (14)0.18771 (18)0.0671 (5)
H80.43840.54820.19000.080*
C10.41734 (9)0.37962 (12)0.32400 (17)0.0558 (5)
C20.35149 (9)0.42921 (13)0.27592 (18)0.0601 (5)
C90.39507 (9)0.21215 (13)0.21512 (17)0.0573 (5)
C100.35904 (10)0.24767 (16)0.09632 (19)0.0715 (6)
H100.35720.31710.07950.086*
C110.32638 (11)0.18184 (19)0.0042 (2)0.0863 (7)
H110.30180.20710.07370.104*
C120.32938 (12)0.0786 (2)0.0254 (2)0.0922 (7)
H120.30600.03440.03650.111*
C130.36692 (11)0.04198 (16)0.1378 (2)0.0798 (6)
H130.37030.02790.15040.096*
C140.40056 (9)0.10649 (12)0.23474 (17)0.0585 (5)
C150.44216 (10)0.06197 (13)0.35114 (19)0.0630 (5)
H10.5357 (13)0.436 (2)0.528 (3)0.135 (9)*
H20.4583 (10)0.2526 (15)0.370 (2)0.082 (7)*
H30.4738 (14)0.062 (2)0.427 (3)0.146 (11)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0527 (9)0.0436 (8)0.0751 (9)0.0023 (7)0.0032 (7)0.0035 (7)
N20.0687 (11)0.0420 (8)0.0697 (10)0.0008 (8)0.0061 (8)0.0020 (7)
O10.0626 (9)0.0518 (7)0.0916 (10)0.0099 (6)0.0169 (7)0.0035 (7)
O20.0590 (9)0.0721 (9)0.1358 (13)0.0170 (8)0.0112 (9)0.0088 (8)
O30.1128 (13)0.0408 (7)0.0948 (11)0.0014 (7)0.0070 (9)0.0030 (7)
O40.0940 (10)0.0445 (7)0.0850 (9)0.0034 (7)0.0045 (8)0.0032 (7)
C30.0521 (11)0.0468 (9)0.0591 (10)0.0024 (8)0.0009 (8)0.0051 (8)
C40.0634 (13)0.0672 (13)0.0871 (14)0.0118 (11)0.0017 (10)0.0187 (10)
C50.107 (2)0.0678 (16)0.119 (2)0.0383 (16)0.0088 (16)0.0215 (14)
C60.151 (3)0.0467 (13)0.1032 (18)0.0222 (17)0.0143 (18)0.0032 (12)
C70.120 (2)0.0592 (13)0.0895 (16)0.0057 (14)0.0121 (14)0.0163 (11)
C80.0728 (14)0.0513 (10)0.0752 (12)0.0046 (10)0.0107 (10)0.0074 (9)
C10.0564 (11)0.0399 (9)0.0675 (11)0.0040 (8)0.0045 (9)0.0062 (8)
C20.0521 (11)0.0513 (10)0.0719 (12)0.0062 (9)0.0014 (9)0.0000 (9)
C90.0579 (11)0.0516 (10)0.0607 (11)0.0052 (9)0.0079 (9)0.0026 (8)
C100.0728 (13)0.0677 (12)0.0698 (12)0.0019 (10)0.0052 (10)0.0027 (10)
C110.0834 (16)0.1003 (18)0.0675 (13)0.0037 (14)0.0019 (11)0.0080 (12)
C120.0937 (18)0.0897 (17)0.0861 (16)0.0113 (14)0.0020 (13)0.0297 (13)
C130.0866 (15)0.0615 (12)0.0891 (15)0.0103 (11)0.0128 (13)0.0194 (11)
C140.0624 (12)0.0468 (10)0.0665 (11)0.0048 (9)0.0137 (9)0.0044 (8)
C150.0708 (13)0.0438 (10)0.0757 (13)0.0023 (9)0.0187 (10)0.0022 (9)
Geometric parameters (Å, º) top
N1—C11.288 (2)C6—C71.371 (4)
N1—O11.4093 (18)C6—H60.9300
N2—C11.364 (2)C7—C81.390 (3)
N2—C91.389 (2)C7—H70.9300
N2—H20.86 (2)C8—H80.9300
O1—H11.02 (3)C1—C21.501 (2)
O2—C21.214 (2)C9—C101.394 (3)
O3—C151.314 (2)C9—C141.408 (2)
O3—H30.96 (3)C10—C111.368 (3)
O4—C151.227 (2)C10—H100.9300
C3—C81.378 (3)C11—C121.376 (3)
C3—C41.386 (2)C11—H110.9300
C3—C21.475 (2)C12—C131.359 (3)
C4—C51.359 (3)C12—H120.9300
C4—H40.9300C13—C141.396 (3)
C5—C61.360 (4)C13—H130.9300
C5—H50.9300C14—C151.463 (3)
C1—N1—O1111.51 (13)N2—C1—C2122.60 (16)
C1—N2—C9128.76 (16)O2—C2—C3121.78 (17)
C1—N2—H2114.5 (14)O2—C2—C1117.86 (16)
C9—N2—H2116.8 (14)C3—C2—C1120.27 (16)
N1—O1—H198.2 (14)N2—C9—C10121.58 (17)
C15—O3—H3110.7 (17)N2—C9—C14120.04 (16)
C8—C3—C4119.42 (18)C10—C9—C14118.32 (16)
C8—C3—C2122.69 (17)C11—C10—C9120.9 (2)
C4—C3—C2117.81 (18)C11—C10—H10119.6
C5—C4—C3120.3 (2)C9—C10—H10119.6
C5—C4—H4119.8C10—C11—C12120.8 (2)
C3—C4—H4119.8C10—C11—H11119.6
C4—C5—C6120.3 (2)C12—C11—H11119.6
C4—C5—H5119.8C13—C12—C11119.3 (2)
C6—C5—H5119.8C13—C12—H12120.3
C5—C6—C7120.8 (2)C11—C12—H12120.3
C5—C6—H6119.6C12—C13—C14121.7 (2)
C7—C6—H6119.6C12—C13—H13119.2
C6—C7—C8119.3 (2)C14—C13—H13119.2
C6—C7—H7120.3C13—C14—C9118.82 (18)
C8—C7—H7120.3C13—C14—C15118.87 (17)
C3—C8—C7119.8 (2)C9—C14—C15122.27 (15)
C3—C8—H8120.1O4—C15—O3121.15 (18)
C7—C8—H8120.1O4—C15—C14124.48 (16)
N1—C1—N2122.75 (16)O3—C15—C14114.36 (18)
N1—C1—C2113.21 (15)
C8—C3—C4—C50.4 (3)N2—C1—C2—C3148.88 (18)
C2—C3—C4—C5177.04 (18)C1—N2—C9—C1018.7 (3)
C3—C4—C5—C60.0 (3)C1—N2—C9—C14164.12 (19)
C4—C5—C6—C70.1 (4)N2—C9—C10—C11178.7 (2)
C5—C6—C7—C80.8 (4)C14—C9—C10—C114.0 (3)
C4—C3—C8—C71.0 (3)C9—C10—C11—C121.3 (3)
C2—C3—C8—C7177.49 (18)C10—C11—C12—C132.0 (4)
C6—C7—C8—C31.2 (3)C11—C12—C13—C142.5 (4)
O1—N1—C1—N22.5 (2)C12—C13—C14—C90.2 (3)
O1—N1—C1—C2169.11 (14)C12—C13—C14—C15177.7 (2)
C9—N2—C1—N1165.87 (18)N2—C9—C14—C13179.26 (18)
C9—N2—C1—C228.8 (3)C10—C9—C14—C133.4 (3)
C8—C3—C2—O2161.11 (19)N2—C9—C14—C153.0 (3)
C4—C3—C2—O215.4 (3)C10—C9—C14—C15174.35 (17)
C8—C3—C2—C122.5 (3)C13—C14—C15—O4179.5 (2)
C4—C3—C2—C1161.02 (17)C9—C14—C15—O42.7 (3)
N1—C1—C2—O2132.09 (19)C13—C14—C15—O31.6 (3)
N2—C1—C2—O234.6 (3)C9—C14—C15—O3176.17 (17)
N1—C1—C2—C344.5 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···N1i1.02 (3)1.83 (3)2.780 (2)154 (2)
O3—H3···O4ii0.96 (3)1.68 (3)2.644 (3)177 (3)
N2—H2···O10.86 (2)2.18 (2)2.548 (2)105.5 (16)
N2—H2···O40.86 (2)2.01 (2)2.667 (2)132.0 (18)
Symmetry codes: (i) x+1, y+1, z+1; (ii) x+1, y, z+1.

Experimental details

Crystal data
Chemical formulaC15H12N2O4
Mr284.27
Crystal system, space groupMonoclinic, C2/c
Temperature (K)293
a, b, c (Å)20.6850 (19), 13.1680 (13), 10.488 (11)
β (°) 101.921 (5)
V3)2795 (3)
Z8
Radiation typeMo Kα
µ (mm1)0.10
Crystal size (mm)0.40 × 0.27 × 0.16
Data collection
DiffractometerStoe IPDS 2
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
12250, 2477, 1472
Rint0.088
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.041, 0.097, 0.86
No. of reflections2477
No. of parameters202
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.22, 0.22

Computer programs: X-AREA (Stoe & Cie, 2002), X-AREA, X-RED (Stoe & Cie, 2002), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···N1i1.02 (3)1.83 (3)2.780 (2)154 (2)
O3—H3···O4ii0.96 (3)1.68 (3)2.644 (3)177 (3)
N2—H2···O10.86 (2)2.18 (2)2.548 (2)105.5 (16)
N2—H2···O40.86 (2)2.01 (2)2.667 (2)132.0 (18)
Symmetry codes: (i) x+1, y+1, z+1; (ii) x+1, y, z+1.
Comparison of selected geometric parameters (Å, °) in the oxime moiety of (I) with those in the related compounds (II), (III) and (IV) top
Bond or angle(I)(II)(III)(IV)
N1-O11.4093 (18)1.4063 (17)1.423 (3)1.429 (4)
N1-C11.288 (2)1.282 (2)1.290 (3)1.241 (6)
C1-C21.501 (2)1.502 (2)1.489 (3)1.551 (7)
C2-C1-N1113.21 (15)113.75 (15)116.59 (19)118.3 (5)
C1-N1-O1111.51 (13)111.00 (14)109.37 (18)112.2 (4)
 

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