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The title compound, C14H12N2O4, shows an E conformation about the diazenyl N atoms. The crystal structure features layers of mol­ecules with the primary connection between the layers afforded by carboxyl­ic acid dimer motifs; no evidence for extensive [pi]-[pi] stacking between the layers was found.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270100010118/sk1403sup1.cif
Contains datablocks global1, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270100010118/sk1403Isup2.hkl
Contains datablock I

CCDC reference: 152638

Comment top

Organotin compounds containing carboxylate ligands similar to that derived from the title compound have received considerable attention recently (Basu Baul & Tiekink, 1998, 1999; Willem et al., 1998). These systems have provided a large number of X-ray-quality crystals enabling systematic analyses and hence conclusions to be drawn as to the reasons why different motifs (Tiekink, 1991, 1994) are found for triorganotin carboxylates (Willem et al., 1998). A key feature of some of these structures is the presence of ππ interactions that serve to stabilize the crystal structure. Surprisingly, relatively little is known about the structural chemistry of diazocarboxylic acid derivatives themselves (Moreiras et al., 1980; van der Sluis & Spek, 1990) and in order to ascertain the reasons why base stacking is observed in some organotin derivatives but not in others, the structure of the title compound, (I) (Fig. 1), was investigated.

The conformation about the diazo group is E and derived interatomic parameters are as expected. The molecule is basically planar although there is a slight twist about the diazo group, as seen in the N1—N2—C8—C9 and N2—N1—C6—C5 torsion angles of 176.4 (2) and 8.5 (3)°, respectively. The dihedral angle between the two aromatic rings is 5.43 (7)°. The carboxylic acid group is coplanar with the C2–C7 ring [O1—C1—C2—C3 is −178.2 (2)°], which facilitates the formation of an intramolecular hydrogen-bonding contacts such that O3···O2 is 2.630 (2) Å (see Table 2). Intermolecular hydrogen-bonding interactions are also present.

The structure may be described as a hydrogen-bonded array in the ac plane that is stacked along b; however, the layers are not flat, there being significant corrugation within them. The arrangement of molecules within the layer is best described as being based on the coronene motif (Desiraju & Gavezzotti, 1989). The layers are stabilized in part by weak hydrogen-bonding interactions between the hydroxyl-H atom and a symmetry-related methoxy-O atom, such that O3···O4i is 3.003 (2) Å [symmetry code: (i) 1/2 + x, y, 1/2 − z]. Contacts of 3.522 (2) Å that occur between translationally related C1 and C5ii atoms throughout the layer are also noted [symmetry code: (ii) x, y, 1 + z]. Connections between the layers are afforded by carboxylic acid dimer formation: O1···O2iii 2.631 (2) Å [symmetry code: (iii) 2 − x, −y, 2 − z]. No evidence was found for extensive π···π interactions in the lattice. However, between layers, centrosymmetrically related pairs of benzoic acid fragments approach each other at distances indicative of π···π interactions. The closest contact of 3.295 (2) Å occurs between C1 and C3iv, and the average separation between the least-squares planes through each of the O2CC6 fragments is 3.24 Å [symmetry code: (iv) 2 − x, −y, 1 − z]. Presumably, π···π interactions involving the methoxyphenyl fragment and hence, the whole molecule, are precluded by the bulky nature of the methyl group. Finally, evidence for a C—H···ring interaction between the layers is also noted, such that the C5—H4···Cpv (where Cp is the centroid of the C2–C7 ring) is 2.78 Å and the angle at H4 is 139° [symmetry code: (v) x, 1/2 − y, 1/2 + z].

Experimental top

Diazo-coupling of p-methoxyaniline and o-hydroxybenzoic acid in alkaline solution yielded the title compound in 52% yield. Recrystallization from -benzene solution gave orange-red crystals (m.p. 482–483 K).

Refinement top

All H atoms were located from a difference map and refined but were fixed in the final cycles of refinement (O—H 0.86 and 0.90 Å; C—H 0.95–1.03 Å).

Computing details top

Data collection: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1999); cell refinement: MSC/AFC Diffractometer Control Software; data reduction: TEXSAN (Molecular Structure Corporation, 1997-1999); program(s) used to solve structure: SIR97 (Altomare et al., 1997); program(s) used to refine structure: TEXSAN; software used to prepare material for publication: TEXSAN.

Figures top
[Figure 1] Fig. 1. The molecular structure and crystallographic numbering scheme for (I). Displacement ellipsoids shown at the 50% probability level (ORTEPII; Johnson, 1976).
(I) top
Crystal data top
C14H12N2O4F(000) = 1136
Mr = 272.26Dx = 1.440 Mg m3
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 25 reflections
a = 24.902 (6) Åθ = 6.4–9.6°
b = 15.109 (6) ŵ = 0.11 mm1
c = 6.674 (2) ÅT = 173 K
V = 2511 (1) Å3Trigonal plate, orange–red
Z = 80.45 × 0.24 × 0.19 mm
Data collection top
Rigaku AFC-7R
diffractometer
Rint = 0.030
Radiation source: X-ray tubeθmax = 27.5°, θmin = 3.1°
Graphite monochromatorh = 032
ω scansk = 119
6617 measured reflectionsl = 88
2894 independent reflections3 standard reflections every 400 reflections
1800 reflections with I > 2σ(I) intensity decay: 1.4%
Refinement top
Refinement on F0 restraints
Least-squares matrix: full0 constraints
R[F2 > 2σ(F2)] = 0.034H-atom parameters not refined
wR(F2) = 0.033Weighting scheme based on measured s.u.'s w = 1/[σ2(Fo) + 0.00001|Fo|2]
S = 1.65(Δ/σ)max < 0.0001
1800 reflectionsΔρmax = 0.24 e Å3
181 parametersΔρmin = 0.20 e Å3
Crystal data top
C14H12N2O4V = 2511 (1) Å3
Mr = 272.26Z = 8
Orthorhombic, PbcaMo Kα radiation
a = 24.902 (6) ŵ = 0.11 mm1
b = 15.109 (6) ÅT = 173 K
c = 6.674 (2) Å0.45 × 0.24 × 0.19 mm
Data collection top
Rigaku AFC-7R
diffractometer
Rint = 0.030
6617 measured reflections3 standard reflections every 400 reflections
2894 independent reflections intensity decay: 1.4%
1800 reflections with I > 2σ(I)
Refinement top
R[F2 > 2σ(F2)] = 0.0340 restraints
wR(F2) = 0.033H-atom parameters not refined
S = 1.65Δρmax = 0.24 e Å3
1800 reflectionsΔρmin = 0.20 e Å3
181 parameters
Special details top

Refinement. All H atoms were located from a difference map and refined (x, y, z and U_iso_) but were fixed in the final cycles of refinement.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.94177 (4)0.01763 (7)0.8390 (2)0.0300 (3)
O21.02771 (4)0.06121 (7)0.8285 (1)0.0288 (3)
O31.06264 (4)0.14755 (7)0.5120 (2)0.0295 (3)
O40.64850 (4)0.11987 (8)0.3216 (2)0.0377 (3)
N10.85392 (5)0.11762 (8)0.2170 (2)0.0297 (4)
N20.84935 (5)0.14252 (8)0.0377 (2)0.0297 (4)
C10.98228 (6)0.0576 (1)0.7523 (2)0.0248 (4)
C20.97032 (6)0.09777 (9)0.5580 (2)0.0227 (4)
C31.01099 (6)0.14092 (9)0.4502 (2)0.0229 (4)
C40.99862 (6)0.18081 (9)0.2668 (2)0.0269 (4)
C50.94770 (6)0.17542 (9)0.1891 (2)0.0263 (4)
C60.90729 (6)0.1298 (1)0.2921 (2)0.0254 (4)
C70.91851 (6)0.0933 (1)0.4770 (2)0.0248 (4)
C80.79720 (6)0.1321 (1)0.0465 (2)0.0275 (4)
C90.79165 (6)0.1644 (1)0.2393 (2)0.0310 (4)
C100.74264 (6)0.1619 (1)0.3383 (2)0.0314 (4)
C110.69877 (6)0.1253 (1)0.2405 (2)0.0278 (4)
C120.70427 (6)0.0913 (1)0.0478 (3)0.0336 (5)
C130.75293 (6)0.0941 (1)0.0491 (2)0.0326 (4)
C140.64184 (7)0.1524 (1)0.5209 (3)0.0506 (6)
H10.95160.00740.95560.053*
H21.06450.12360.62880.057*
H31.02620.21320.19860.031*
H40.94020.20350.06420.022*
H50.89110.06370.54870.027*
H60.82190.19280.30320.046*
H70.73970.18580.47560.037*
H80.67440.06260.01500.051*
H90.75770.06950.18440.040*
H100.66430.11850.61540.092*
H110.65020.21930.52580.071*
H120.60560.14440.55210.051*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0274 (6)0.0382 (6)0.0244 (6)0.0033 (5)0.0005 (5)0.0082 (5)
O20.0253 (6)0.0378 (6)0.0232 (5)0.0029 (5)0.0038 (5)0.0042 (5)
O30.0224 (5)0.0387 (7)0.0275 (6)0.0022 (5)0.0023 (5)0.0052 (5)
O40.0250 (6)0.0536 (7)0.0345 (7)0.0067 (6)0.0060 (5)0.0073 (6)
N10.0266 (7)0.0316 (7)0.0310 (8)0.0005 (6)0.0054 (6)0.0029 (6)
N20.0250 (7)0.0346 (8)0.0294 (7)0.0014 (6)0.0035 (6)0.0017 (6)
C10.0271 (8)0.0239 (8)0.0233 (8)0.0011 (6)0.0014 (7)0.0036 (7)
C20.0248 (8)0.0221 (7)0.0211 (7)0.0027 (6)0.0007 (6)0.0011 (6)
C30.0212 (7)0.0233 (8)0.0242 (8)0.0014 (6)0.0001 (6)0.0034 (7)
C40.0271 (8)0.0267 (8)0.0269 (8)0.0016 (6)0.0022 (7)0.0029 (7)
C50.0288 (8)0.0261 (8)0.0238 (8)0.0016 (6)0.0016 (7)0.0036 (7)
C60.0229 (8)0.0270 (8)0.0262 (8)0.0018 (6)0.0025 (6)0.0018 (7)
C70.0238 (8)0.0237 (8)0.0270 (8)0.0015 (6)0.0019 (7)0.0001 (7)
C80.0234 (8)0.0306 (9)0.0283 (8)0.0010 (7)0.0038 (7)0.0007 (7)
C90.0236 (8)0.040 (1)0.0290 (9)0.0031 (7)0.0011 (7)0.0037 (8)
C100.0296 (8)0.039 (1)0.0252 (8)0.0020 (7)0.0021 (7)0.0054 (8)
C110.0241 (8)0.0298 (8)0.0297 (9)0.0005 (6)0.0043 (7)0.0017 (7)
C120.0271 (9)0.041 (1)0.0326 (9)0.0094 (7)0.0002 (7)0.0057 (8)
C130.0322 (9)0.037 (1)0.0281 (8)0.0025 (7)0.0028 (7)0.0061 (8)
C140.033 (1)0.076 (1)0.042 (1)0.0099 (9)0.0152 (9)0.017 (1)
Geometric parameters (Å, º) top
O1—C11.311 (2)C5—H40.95
O1—H10.90C6—C71.380 (3)
O2—C11.241 (2)C7—H50.95
O3—C31.355 (2)C8—C91.383 (3)
O3—H20.86C8—C131.397 (3)
O4—C111.367 (2)C9—C101.388 (3)
O4—C141.427 (3)C9—H60.97
N1—N21.260 (2)C10—C111.388 (3)
N1—C61.432 (2)C10—H70.99
N2—C81.424 (2)C11—C121.392 (3)
C1—C21.462 (3)C12—C131.374 (3)
C2—C31.403 (2)C12—H80.96
C2—C71.400 (2)C13—H90.98
C3—C41.398 (3)C14—H100.99
C4—C51.372 (3)C14—H111.03
C4—H30.96C14—H120.93
C5—C61.401 (2)
O1···O2i2.631 (2)O3···C4vi3.487 (2)
O1···H12ii2.8133O4···H2viii2.4561
O1···H1i2.9916O4···N1ix3.598 (3)
O1···N2iii3.258 (2)N1···H6vi2.9758
O1···C3iv3.294 (2)N2···H6vi2.7898
O1···C5iii3.341 (2)N2···C9vi3.576 (3)
O1···C4iv3.419 (2)C1···H1i2.6617
O1···O3iv3.425 (2)C1···C3iv3.295 (3)
O1···C14ii3.436 (3)C1···C2iv3.346 (3)
O1···C1i3.508 (2)C1···C5iii3.522 (3)
O1···C6iii3.571 (2)C2···C2iv3.393 (4)
O2···H1i1.7325C2···C5vi3.581 (3)
O2···H12v2.7520C3···H3vi2.7838
O2···O4v3.136 (2)C3···H4vi3.0344
O2···O2i3.251 (3)C3···C4vi3.437 (3)
O2···C1i3.334 (2)C3···C5vi3.567 (3)
O2···C7iv3.376 (2)C4···H4vi3.0178
O2···C6iv3.405 (2)C11···H11vi3.0049
O2···C14v3.409 (3)H1···H1i2.4915
O2···C4iii3.514 (2)H1···H12ii2.5136
O2···C2iv3.525 (2)H2···H3vi2.6843
O2···C5iii3.569 (2)H3···H12x2.4392
O3···H3vi2.6076H5···H8xi2.5198
O3···H11vii2.9674H8···H10iii2.6201
O3···O4v3.003 (2)
C1—O1—H1111.5C6—C7—H5119.7
C3—O3—H2107.2N2—C8—C9114.8 (2)
C11—O4—C14117.1 (2)N2—C8—C13125.8 (2)
N2—N1—C6112.2 (2)C9—C8—C13119.4 (2)
N1—N2—C8115.1 (2)C8—C9—C10121.4 (2)
O1—C1—O2122.7 (2)C8—C9—H6119.3
O1—C1—C2115.2 (2)C10—C9—H6119.2
O2—C1—C2122.1 (2)C9—C10—C11118.6 (2)
C1—C2—C3120.0 (2)C9—C10—H7119.9
C1—C2—C7120.7 (2)C11—C10—H7121.5
C3—C2—C7119.3 (2)O4—C11—C10124.0 (2)
O3—C3—C2124.3 (2)O4—C11—C12115.7 (2)
O3—C3—C4116.3 (2)C10—C11—C12120.3 (2)
C2—C3—C4119.3 (2)C11—C12—C13120.7 (2)
C3—C4—C5120.6 (2)C11—C12—H8119.7
C3—C4—H3118.5C13—C12—H8119.5
C5—C4—H3120.9C8—C13—C12119.6 (2)
C4—C5—C6120.5 (2)C8—C13—H9118.6
C4—C5—H4119.0C12—C13—H9121.8
C6—C5—H4120.5O4—C14—H10110.6
N1—C6—C5123.9 (2)O4—C14—H11110.1
N1—C6—C7116.7 (2)O4—C14—H12106.0
C5—C6—C7119.4 (2)H10—C14—H11112.0
C2—C7—C6120.8 (2)H10—C14—H12109.7
C2—C7—H5119.5H11—C14—H12108.2
O1—C1—C2—C3178.8 (2)C1—C2—C3—C4178.5 (2)
O1—C1—C2—C70.8 (3)C1—C2—C7—C6178.9 (2)
O2—C1—C2—C30.9 (3)C2—C3—C4—C52.2 (3)
O2—C1—C2—C7179.4 (2)C2—C7—C6—C53.0 (3)
O3—C3—C2—C11.2 (3)C3—C2—C7—C60.8 (3)
O3—C3—C2—C7178.5 (2)C3—C4—C5—C60.1 (3)
O3—C3—C4—C5178.1 (2)C4—C3—C2—C71.8 (3)
O4—C11—C10—C9179.4 (2)C4—C5—C6—C72.7 (3)
O4—C11—C12—C13179.3 (2)C6—N1—N2—C8179.9 (2)
N1—N2—C8—C9176.4 (2)C8—C9—C10—C110.7 (3)
N1—N2—C8—C132.9 (3)C8—C13—C12—C110.5 (3)
N1—C6—C5—C4177.0 (2)C9—C8—C13—C121.6 (3)
N1—C6—C7—C2176.7 (2)C9—C10—C11—C120.4 (3)
N2—N1—C6—C58.5 (3)C10—C9—C8—C131.7 (3)
N2—N1—C6—C7171.1 (2)C10—C11—O4—C141.5 (3)
N2—C8—C9—C10177.6 (2)C10—C11—C12—C130.5 (3)
N2—C8—C13—C12177.6 (2)C12—C11—O4—C14178.6 (2)
Symmetry codes: (i) x+2, y, z+2; (ii) x+3/2, y, z+3/2; (iii) x, y, z+1; (iv) x+2, y, z+1; (v) x+1/2, y, z+1/2; (vi) x, y+1/2, z+1/2; (vii) x+1/2, y+1/2, z; (viii) x1/2, y, z+1/2; (ix) x+3/2, y, z1/2; (x) x+1/2, y, z1/2; (xi) x+3/2, y, z+1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O2i0.901.732.631 (2)176
O3—H2···O20.861.872.630 (2)146
O3—H2···O4v0.862.463.003 (2)122
Symmetry codes: (i) x+2, y, z+2; (v) x+1/2, y, z+1/2.

Experimental details

Crystal data
Chemical formulaC14H12N2O4
Mr272.26
Crystal system, space groupOrthorhombic, Pbca
Temperature (K)173
a, b, c (Å)24.902 (6), 15.109 (6), 6.674 (2)
V3)2511 (1)
Z8
Radiation typeMo Kα
µ (mm1)0.11
Crystal size (mm)0.45 × 0.24 × 0.19
Data collection
DiffractometerRigaku AFC-7R
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
6617, 2894, 1800
Rint0.030
(sin θ/λ)max1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.034, 0.033, 1.65
No. of reflections1800
No. of parameters181
H-atom treatmentH-atom parameters not refined
Δρmax, Δρmin (e Å3)0.24, 0.20

Computer programs: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1999), MSC/AFC Diffractometer Control Software, TEXSAN (Molecular Structure Corporation, 1997-1999), SIR97 (Altomare et al., 1997), TEXSAN.

Selected geometric parameters (Å, º) top
O1—C11.311 (2)O4—C141.427 (3)
O2—C11.241 (2)N1—N21.260 (2)
O3—C31.355 (2)N1—C61.432 (2)
O4—C111.367 (2)N2—C81.424 (2)
C11—O4—C14117.1 (2)O1—C1—O2122.7 (2)
N2—N1—C6112.2 (2)O1—C1—C2115.2 (2)
N1—N2—C8115.1 (2)O2—C1—C2122.1 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O2i0.901.732.631 (2)176.4
O3—H2···O20.861.872.630 (2)146.1
O3—H2···O4ii0.862.463.003 (2)122.0
Symmetry codes: (i) x+2, y, z+2; (ii) x+1/2, y, z+1/2.
 

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