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The crystal structures of 2-hy­droxy-5-[(E)-(4-nitro­phen­yl)diazen­yl]benzoic acid, C13H9N3O5, (I), ammonium 2-hy­droxy-5-[(E)-phenyl­diazen­yl]benzoate, NH4+·C13H9N2O3, (II), and sodium 2-hy­droxy-5-[(E)-(4-nitro­phen­yl)diazen­yl]benzoate trihydrate, Na+·C13H8N3O5·3H2O, (III), have been determined using single-crystal X-ray diffraction. In (I) and (III), the phenyl­diazenyl and carb­oxy­lic acid/carboxyl­ate groups are in an anti orientation with respect to each other, which is in accord with the results of density functional theory (DFT) calculations, whereas in (II), the anion adopts a syn conformation. In (I), mol­ecules form slanted stacks along the [100] direction. In (II), anions form bilayers parallel to (010), the inner part of the bilayers being formed by the benzene rings, with the –OH and –COO substituents on the bilayer surface. The NH4+ cations in (II) are located between the bilayers and are engaged in numerous N—H...O hydrogen bonds. In (III), anions form layers parallel to (001). Both Na+ cations have a distorted octa­hedral environment, with four octa­hedra edge-shared by bridging water O atoms, forming [Na4(H2O)12]4+ units.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229614007827/yf3059sup1.cif
Contains datablocks global, III, I, II

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229614007827/yf3059Isup2.hkl
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229614007827/yf3059IIsup3.hkl
Contains datablock II

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229614007827/yf3059IIIsup4.hkl
Contains datablock III

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229614007827/yf3059Isup5.cml
Supplementary material

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229614007827/yf3059IIsup6.cml
Supplementary material

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229614007827/yf3059IIIsup7.cml
Supplementary material

pdf

Portable Document Format (PDF) file https://doi.org/10.1107/S2053229614007827/yf3059sup8.pdf
Three supplementary figures

CCDC references: 996074; 996075; 996076

Computing details top

For all structures, data collection: X-AREA (Stoe & Cie, 2012); cell refinement: X-AREA (Stoe & Cie, 2012); data reduction: X-RED32 (Stoe & Cie, 2012); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009) and publCIF (Westrip, 2010).

2-Hydroxy-5-[(E)-(4-nitrophenyl)diazenyl]benzoic acid (I) top
Crystal data top
C13H9N3O5F(000) = 592.0
Mr = 287.23Dx = 1.540 Mg m3
Monoclinic, P21/cMelting point: 530 K
Hall symbol: -P 2ybcCu Kα radiation, λ = 1.54186 Å
a = 4.9319 (5) ÅCell parameters from 2234 reflections
b = 11.6649 (14) Åθ = 3.8–56.3°
c = 21.619 (2) ŵ = 1.04 mm1
β = 94.991 (8)°T = 293 K
V = 1239.0 (2) Å3Needle, red–orange
Z = 40.12 × 0.04 × 0.03 mm
Data collection top
Stoe STADI VARI
diffractometer
2334 independent reflections
Radiation source: microfocus sealed tube1804 reflections with I > 2σ(I)
None monochromatorRint = 0.074
Detector resolution: 5.81 pixels mm-1θmax = 70.0°, θmin = 4.1°
rotation method scansh = 56
Absorption correction: multi-scan
(Blessing, 1995)
k = 1413
Tmin = 0.925, Tmax = 0.979l = 2226
14169 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.041H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.119 w = 1/[σ2(Fo2) + (0.0832P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.00(Δ/σ)max < 0.001
2334 reflectionsΔρmax = 0.22 e Å3
199 parametersΔρmin = 0.18 e Å3
4 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0143 (13)
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. The C-bound H atoms were placed in idealized positions, with constrained distances of 0.93 Å and with Uiso(H) = 1.2Ueq(C). Phenol and carboxylic H atoms were restrained so that to reproduce the C—O—H angle values observed in salicylic acid (neutron structure determination, Bacon et al., 1973): 107° for phenol and 109° for COOH group.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O11.1662 (2)0.16995 (10)0.01162 (5)0.0516 (3)
H11.259 (4)0.2232 (6)0.0226 (7)0.086 (8)*
O21.3733 (2)0.37681 (10)0.00850 (5)0.0529 (3)
O31.2554 (2)0.50125 (10)0.06235 (6)0.0559 (3)
H131.370 (3)0.5406 (7)0.0471 (7)0.074 (6)*
O40.3794 (3)0.26095 (12)0.40909 (6)0.0658 (4)
O50.3102 (3)0.44066 (11)0.39742 (6)0.0676 (4)
N10.5734 (3)0.30930 (12)0.18177 (6)0.0470 (3)
N20.4515 (3)0.22991 (13)0.20677 (6)0.0508 (4)
N30.2672 (3)0.34058 (12)0.38566 (6)0.0488 (3)
C11.0527 (3)0.31879 (13)0.05999 (6)0.0395 (3)
C21.0260 (3)0.20830 (13)0.03457 (6)0.0413 (4)
C30.8421 (3)0.13098 (14)0.05774 (7)0.0482 (4)
H30.82030.05830.04040.058*
C40.6948 (3)0.16214 (14)0.10573 (7)0.0469 (4)
H40.57390.11010.12090.056*
C50.7233 (3)0.27134 (13)0.13239 (7)0.0423 (4)
C60.8975 (3)0.34931 (13)0.10875 (7)0.0417 (4)
H60.91220.42280.12530.050*
C70.2843 (3)0.26631 (14)0.25364 (7)0.0458 (4)
C80.2244 (3)0.37942 (15)0.26665 (7)0.0510 (4)
H80.30360.43860.24570.061*
C90.0471 (3)0.40402 (15)0.31068 (7)0.0506 (4)
H90.00630.47960.32000.061*
C100.0687 (3)0.31457 (14)0.34076 (6)0.0435 (4)
C110.0092 (3)0.20176 (15)0.32949 (8)0.0522 (4)
H110.08720.14310.35100.063*
C120.1689 (4)0.17777 (15)0.28548 (8)0.0534 (4)
H120.21190.10210.27710.064*
C131.2401 (3)0.40097 (13)0.03518 (7)0.0422 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0522 (7)0.0533 (7)0.0528 (6)0.0086 (5)0.0242 (5)0.0106 (5)
O20.0544 (7)0.0533 (7)0.0554 (6)0.0111 (5)0.0299 (5)0.0075 (5)
O30.0622 (7)0.0464 (6)0.0640 (7)0.0148 (5)0.0344 (6)0.0092 (5)
O40.0675 (8)0.0678 (8)0.0679 (8)0.0032 (6)0.0393 (6)0.0040 (6)
O50.0713 (9)0.0625 (8)0.0725 (8)0.0196 (6)0.0272 (6)0.0011 (6)
N10.0430 (7)0.0571 (8)0.0426 (7)0.0059 (6)0.0141 (5)0.0007 (6)
N20.0491 (8)0.0597 (8)0.0463 (7)0.0077 (6)0.0197 (6)0.0011 (6)
N30.0450 (7)0.0584 (8)0.0446 (7)0.0076 (6)0.0132 (5)0.0027 (6)
C10.0354 (7)0.0450 (8)0.0391 (7)0.0024 (6)0.0092 (6)0.0013 (6)
C20.0364 (7)0.0495 (8)0.0390 (7)0.0009 (6)0.0095 (6)0.0021 (6)
C30.0496 (9)0.0461 (8)0.0506 (9)0.0083 (7)0.0146 (7)0.0049 (7)
C40.0441 (8)0.0493 (8)0.0492 (8)0.0098 (7)0.0145 (7)0.0029 (7)
C50.0383 (8)0.0508 (8)0.0390 (7)0.0031 (6)0.0107 (6)0.0003 (6)
C60.0409 (8)0.0444 (8)0.0415 (7)0.0043 (6)0.0129 (6)0.0026 (6)
C70.0429 (8)0.0561 (9)0.0399 (7)0.0042 (7)0.0118 (6)0.0009 (6)
C80.0534 (9)0.0538 (9)0.0479 (8)0.0092 (7)0.0165 (7)0.0061 (7)
C90.0564 (10)0.0479 (9)0.0490 (8)0.0008 (7)0.0135 (7)0.0017 (7)
C100.0412 (8)0.0537 (9)0.0369 (7)0.0014 (7)0.0112 (6)0.0025 (6)
C110.0561 (10)0.0508 (9)0.0534 (9)0.0038 (7)0.0255 (7)0.0051 (7)
C120.0603 (10)0.0487 (9)0.0546 (9)0.0025 (7)0.0252 (8)0.0009 (7)
C130.0391 (8)0.0459 (8)0.0433 (8)0.0035 (6)0.0134 (6)0.0004 (6)
Geometric parameters (Å, º) top
O1—C21.3400 (17)C3—H30.9300
O1—H10.820 (14)C4—C51.400 (2)
O2—C131.2290 (17)C4—H40.9300
O3—C131.3081 (19)C5—C61.379 (2)
O3—H130.820 (13)C6—H60.9300
O4—N31.2142 (18)C7—C81.386 (2)
O5—N31.2173 (19)C7—C121.390 (2)
N1—N21.2519 (19)C8—C91.378 (2)
N1—C51.4213 (19)C8—H80.9300
N2—C71.4256 (19)C9—C101.379 (2)
N3—C101.4691 (19)C9—H90.9300
C1—C61.4014 (19)C10—C111.375 (2)
C1—C21.403 (2)C11—C121.378 (2)
C1—C131.4653 (19)C11—H110.9300
C2—C31.402 (2)C12—H120.9300
C3—C41.367 (2)
C2—O1—H1107.5 (10)C5—C6—H6119.7
C13—O3—H13109.6 (8)C1—C6—H6119.7
N2—N1—C5113.24 (13)C8—C7—C12120.18 (14)
N1—N2—C7114.56 (14)C8—C7—N2125.06 (14)
O4—N3—O5123.55 (13)C12—C7—N2114.70 (15)
O4—N3—C10118.15 (13)C9—C8—C7119.86 (15)
O5—N3—C10118.30 (14)C9—C8—H8120.1
C6—C1—C2119.29 (13)C7—C8—H8120.1
C6—C1—C13120.81 (13)C8—C9—C10118.81 (16)
C2—C1—C13119.89 (12)C8—C9—H9120.6
O1—C2—C3116.31 (13)C10—C9—H9120.6
O1—C2—C1124.17 (13)C11—C10—C9122.48 (14)
C3—C2—C1119.51 (13)C11—C10—N3118.66 (14)
C4—C3—C2120.22 (14)C9—C10—N3118.85 (15)
C4—C3—H3119.9C10—C11—C12118.38 (15)
C2—C3—H3119.9C10—C11—H11120.8
C3—C4—C5120.88 (14)C12—C11—H11120.8
C3—C4—H4119.6C11—C12—C7120.26 (16)
C5—C4—H4119.6C11—C12—H12119.9
C6—C5—C4119.40 (13)C7—C12—H12119.9
C6—C5—N1117.03 (13)O2—C13—O3122.43 (13)
C4—C5—N1123.52 (13)O2—C13—C1121.83 (14)
C5—C6—C1120.64 (14)O3—C13—C1115.74 (12)
C5—N1—N2—C7175.91 (12)C12—C7—C8—C90.8 (3)
C6—C1—C2—O1179.33 (14)N2—C7—C8—C9176.20 (15)
C13—C1—C2—O11.1 (2)C7—C8—C9—C100.4 (3)
C6—C1—C2—C30.9 (2)C8—C9—C10—C111.5 (3)
C13—C1—C2—C3178.70 (14)C8—C9—C10—N3177.25 (14)
O1—C2—C3—C4178.64 (14)O4—N3—C10—C113.1 (2)
C1—C2—C3—C41.6 (2)O5—N3—C10—C11176.89 (16)
C2—C3—C4—C50.3 (2)O4—N3—C10—C9175.76 (15)
C3—C4—C5—C61.7 (2)O5—N3—C10—C94.3 (2)
C3—C4—C5—N1179.13 (15)C9—C10—C11—C121.4 (3)
N2—N1—C5—C6170.02 (13)N3—C10—C11—C12177.42 (15)
N2—N1—C5—C412.4 (2)C10—C11—C12—C70.1 (3)
C4—C5—C6—C12.3 (2)C8—C7—C12—C111.0 (3)
N1—C5—C6—C1179.96 (13)N2—C7—C12—C11176.32 (16)
C2—C1—C6—C51.0 (2)C6—C1—C13—O2178.27 (14)
C13—C1—C6—C5179.36 (13)C2—C1—C13—O21.3 (2)
N1—N2—C7—C88.5 (2)C6—C1—C13—O31.5 (2)
N1—N2—C7—C12174.29 (14)C2—C1—C13—O3178.89 (14)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O20.82 (1)1.90 (1)2.6189 (16)147 (1)
O1—H1···O4i0.82 (1)2.42 (1)3.0461 (18)134 (1)
O3—H13···O2ii0.82 (1)1.85 (1)2.6651 (16)176 (1)
C4—H4···O5iii0.932.383.202 (2)147
Symmetry codes: (i) x+2, y+1/2, z1/2; (ii) x+3, y+1, z; (iii) x, y1/2, z+1/2.
Ammonium 2-hydroxy-5-[(E)-phenyldiazenyl]benzoate (II) top
Crystal data top
NH4+·C13H9N2O3F(000) = 544
Mr = 259.26Dx = 1.355 Mg m3
Monoclinic, P21/nCu Kα radiation, λ = 1.54186 Å
Hall symbol: -P 2ynCell parameters from 3698 reflections
a = 6.0471 (1) Åθ = 5.1–72.1°
b = 34.371 (1) ŵ = 0.82 mm1
c = 6.2824 (2) ÅT = 293 K
β = 103.278 (2)°Irregular block, dark yellow
V = 1270.85 (6) Å30.08 × 0.05 × 0.05 mm
Z = 4
Data collection top
Stoe STADI VARI
diffractometer
2352 independent reflections
Radiation source: microfocus sealed tube1561 reflections with I > 2σ(I)
None monochromatorRint = 0.052
Detector resolution: 5.81 pixels mm-1θmax = 69.0°, θmin = 5.2°
rotation method scansh = 76
Absorption correction: multi-scan
(Blessing, 1995)
k = 4141
Tmin = 0.945, Tmax = 0.960l = 77
15094 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.048H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.141 w = 1/[σ2(Fo2) + (0.063P)2 + 0.38P]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max < 0.001
2352 reflectionsΔρmax = 0.14 e Å3
189 parametersΔρmin = 0.16 e Å3
12 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0052 (7)
Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'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 s.u.'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. The C-bound H atoms were placed in idealized positions, with constrained distances of 0.93 Å and with Uiso(H) = 1.2Ueq(C). Phenol H atoms were restrained so that to reproduce the C—O—H angle value of 107° observed in salicylic acid (neutron structure determination, Bacon et al., 1973). All N—H distances and tetrahedral environment of the N atom were also restrained.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.2531 (3)0.05503 (5)0.8971 (3)0.0534 (5)
H10.370 (3)0.0422 (7)0.930 (3)0.087 (12)*
O20.6199 (3)0.02302 (5)0.8656 (3)0.0539 (5)
O30.7530 (3)0.03045 (5)0.5682 (3)0.0534 (5)
N10.2848 (4)0.14683 (5)0.1780 (4)0.0512 (5)
N20.4682 (4)0.14854 (6)0.1187 (4)0.0508 (5)
C10.4416 (4)0.06971 (6)0.6068 (4)0.0403 (5)
C20.2647 (4)0.07579 (6)0.7175 (4)0.0432 (5)
C30.0987 (4)0.10345 (7)0.6398 (4)0.0499 (6)
H30.01930.10710.71010.060*
C40.1077 (4)0.12544 (7)0.4601 (4)0.0509 (6)
H40.00660.14340.40720.061*
C50.2866 (4)0.12113 (6)0.3555 (4)0.0456 (6)
C60.4488 (4)0.09291 (6)0.4288 (4)0.0425 (5)
H60.56560.08940.35670.051*
C70.4620 (4)0.17474 (7)0.0590 (4)0.0495 (6)
C80.2868 (5)0.20058 (7)0.1365 (5)0.0634 (8)
H80.16500.20220.06960.076*
C90.2935 (6)0.22386 (8)0.3135 (6)0.0771 (10)
H90.17630.24140.36480.093*
C100.4716 (6)0.22141 (8)0.4152 (5)0.0723 (9)
H100.47260.23670.53730.087*
C110.6476 (6)0.19641 (9)0.3356 (5)0.0703 (8)
H110.76960.19500.40250.084*
C120.6445 (5)0.17321 (8)0.1560 (5)0.0619 (7)
H120.76550.15660.10090.074*
C130.6177 (4)0.03893 (6)0.6836 (4)0.0421 (5)
N30.0209 (3)0.03147 (5)1.2283 (3)0.0487 (5)
H210.087 (3)0.0405 (6)1.331 (2)0.073*
H220.127 (3)0.0243 (6)1.111 (2)0.073*
H230.066 (3)0.0499 (4)1.191 (3)0.073*
H240.065 (3)0.0110 (4)1.281 (3)0.073*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0507 (11)0.0624 (11)0.0521 (11)0.0042 (8)0.0223 (9)0.0090 (8)
O20.0459 (10)0.0673 (11)0.0499 (10)0.0061 (8)0.0140 (9)0.0170 (8)
O30.0461 (9)0.0588 (10)0.0618 (11)0.0132 (7)0.0258 (9)0.0138 (8)
N10.0489 (11)0.0437 (10)0.0638 (14)0.0045 (8)0.0186 (11)0.0046 (9)
N20.0469 (11)0.0476 (11)0.0605 (14)0.0030 (8)0.0174 (11)0.0067 (9)
C10.0376 (12)0.0407 (11)0.0444 (13)0.0014 (8)0.0129 (11)0.0016 (9)
C20.0442 (12)0.0410 (12)0.0481 (14)0.0040 (9)0.0184 (12)0.0008 (10)
C30.0446 (13)0.0515 (13)0.0590 (16)0.0055 (10)0.0231 (12)0.0027 (11)
C40.0459 (13)0.0425 (12)0.0680 (17)0.0072 (10)0.0206 (13)0.0005 (11)
C50.0460 (13)0.0398 (11)0.0521 (15)0.0018 (9)0.0136 (12)0.0034 (10)
C60.0384 (12)0.0443 (12)0.0468 (13)0.0002 (9)0.0141 (11)0.0011 (10)
C70.0488 (14)0.0438 (12)0.0585 (16)0.0022 (10)0.0178 (13)0.0029 (11)
C80.0599 (16)0.0523 (15)0.083 (2)0.0089 (12)0.0273 (16)0.0201 (14)
C90.076 (2)0.0567 (17)0.103 (3)0.0123 (14)0.031 (2)0.0335 (16)
C100.084 (2)0.0585 (17)0.078 (2)0.0127 (15)0.0248 (19)0.0154 (14)
C110.0701 (19)0.0738 (19)0.076 (2)0.0055 (15)0.0348 (18)0.0052 (16)
C120.0557 (16)0.0593 (16)0.077 (2)0.0044 (12)0.0273 (16)0.0078 (13)
C130.0355 (11)0.0444 (12)0.0463 (13)0.0028 (9)0.0092 (11)0.0027 (10)
N30.0473 (11)0.0484 (11)0.0536 (13)0.0040 (8)0.0182 (10)0.0039 (9)
Geometric parameters (Å, º) top
O1—C21.350 (3)C6—H60.9300
O1—H10.82 (2)C7—C121.379 (3)
O2—C131.265 (3)C7—C81.383 (4)
O3—C131.246 (3)C8—C91.378 (4)
N1—N21.249 (3)C8—H80.9300
N1—C51.421 (3)C9—C101.375 (4)
N2—C71.428 (3)C9—H90.9300
C1—C61.382 (3)C10—C111.370 (4)
C1—C21.419 (3)C10—H100.9300
C1—C131.500 (3)C11—C121.385 (4)
C2—C31.387 (3)C11—H110.9300
C3—C41.370 (3)C12—H120.9300
C3—H30.9300N3—H210.89 (2)
C4—C51.397 (3)N3—H220.89 (2)
C4—H40.9300N3—H230.89 (2)
C5—C61.381 (3)N3—H240.89 (2)
C2—O1—H1106.6 (14)C9—C8—C7119.7 (3)
N2—N1—C5114.6 (2)C9—C8—H8120.2
N1—N2—C7113.4 (2)C7—C8—H8120.2
C6—C1—C2118.6 (2)C10—C9—C8120.7 (3)
C6—C1—C13121.01 (19)C10—C9—H9119.7
C2—C1—C13120.4 (2)C8—C9—H9119.7
O1—C2—C3119.0 (2)C11—C10—C9119.6 (3)
O1—C2—C1121.4 (2)C11—C10—H10120.2
C3—C2—C1119.6 (2)C9—C10—H10120.2
C4—C3—C2120.4 (2)C10—C11—C12120.2 (3)
C4—C3—H3119.8C10—C11—H11119.9
C2—C3—H3119.8C12—C11—H11119.9
C3—C4—C5120.7 (2)C7—C12—C11120.0 (3)
C3—C4—H4119.6C7—C12—H12120.0
C5—C4—H4119.6C11—C12—H12120.0
C6—C5—C4119.0 (2)O3—C13—O2123.6 (2)
C6—C5—N1125.1 (2)O3—C13—C1119.4 (2)
C4—C5—N1115.9 (2)O2—C13—C1117.1 (2)
C5—C6—C1121.5 (2)H21—N3—H22110 (2)
C5—C6—H6119.2H21—N3—H23110 (2)
C1—C6—H6119.2H22—N3—H23109 (2)
C12—C7—C8119.7 (2)H21—N3—H24109 (2)
C12—C7—N2116.2 (2)H22—N3—H24110 (2)
C8—C7—N2124.1 (2)H23—N3—H24109 (2)
C5—N1—N2—C7179.7 (2)C13—C1—C6—C5179.5 (2)
C6—C1—C2—O1177.6 (2)N1—N2—C7—C12169.5 (2)
C13—C1—C2—O11.9 (3)N1—N2—C7—C810.1 (4)
C6—C1—C2—C32.8 (3)C12—C7—C8—C91.6 (4)
C13—C1—C2—C3177.8 (2)N2—C7—C8—C9178.0 (3)
O1—C2—C3—C4178.9 (2)C7—C8—C9—C100.6 (5)
C1—C2—C3—C41.4 (4)C8—C9—C10—C112.0 (5)
C2—C3—C4—C51.6 (4)C9—C10—C11—C121.1 (5)
C3—C4—C5—C63.3 (4)C8—C7—C12—C112.5 (4)
C3—C4—C5—N1176.8 (2)N2—C7—C12—C11177.2 (3)
N2—N1—C5—C615.3 (3)C10—C11—C12—C71.1 (5)
N2—N1—C5—C4164.9 (2)C6—C1—C13—O310.1 (3)
C4—C5—C6—C11.9 (4)C2—C1—C13—O3170.4 (2)
N1—C5—C6—C1178.2 (2)C6—C1—C13—O2169.6 (2)
C2—C1—C6—C51.1 (3)C2—C1—C13—O29.9 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O20.82 (2)1.78 (2)2.524 (3)151 (2)
N3—H21···O3i0.89 (2)1.99 (2)2.788 (3)150 (2)
N3—H22···O2ii0.89 (2)1.91 (2)2.779 (3)164 (2)
N3—H23···O10.89 (2)2.38 (2)3.052 (3)132 (2)
N3—H24···O3iii0.89 (2)1.91 (2)2.799 (3)172 (2)
Symmetry codes: (i) x1, y, z+1; (ii) x1, y, z; (iii) x+1, y, z+2.
Sodium 2-hydroxy-5-[(E)-(4-nitrophenyl)diazenyl]benzoate trihydrate (III) top
Crystal data top
Na+·C13H8N3O5·3H2OZ = 4
Mr = 363.26F(000) = 752
Triclinic, P1Dx = 1.572 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.2123 (5) ÅCell parameters from 5966 reflections
b = 13.0205 (8) Åθ = 2.4–30.4°
c = 17.0317 (11) ŵ = 0.16 mm1
α = 77.185 (6)°T = 293 K
β = 80.933 (5)°Irregular block, dark yellow
γ = 83.401 (5)°0.50 × 0.45 × 0.40 mm
V = 1534.76 (17) Å3
Data collection top
Stoe STADI VARI
diffractometer
5936 independent reflections
Radiation source: fine-focus sealed tube3776 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.026
Detector resolution: 5.81 pixels mm-1θmax = 26.0°, θmin = 2.7°
rotation method scansh = 48
Absorption correction: multi-scan
(Blessing, 1995)
k = 1516
Tmin = 0.926, Tmax = 0.952l = 1920
6773 measured 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) = 0.120H atoms treated by a mixture of independent and constrained refinement
S = 0.92 w = 1/[σ2(Fo2) + (0.0662P)2]
where P = (Fo2 + 2Fc2)/3
5936 reflections(Δ/σ)max < 0.001
493 parametersΔρmax = 0.21 e Å3
22 restraintsΔρmin = 0.26 e Å3
Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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. The C-bound H atoms were placed in idealized positions, with constrained distances of 0.93 Å and with Uiso(H) = 1.2Ueq(C). Phenol H atoms were restrained so that to reproduce the C—O—H angle value of 107° observed in salicylic acid (neutron structure determination, Bacon et al., 1973). For all water molecules, the O—H distances and H—O—H angles of 106° were restrained.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Na10.29209 (14)0.54778 (7)0.04310 (5)0.0411 (2)
Na20.12688 (15)0.81138 (8)0.01809 (6)0.0489 (3)
O200.0003 (2)0.63987 (14)0.01501 (10)0.0413 (4)
H210.085 (2)0.651 (2)0.0511 (11)0.062*
H220.055 (3)0.630 (2)0.0212 (11)0.062*
O300.5998 (3)0.48619 (14)0.09144 (10)0.0447 (4)
H310.597 (4)0.4339 (14)0.1286 (12)0.067*
H320.681 (3)0.5201 (19)0.0997 (17)0.067*
O400.4292 (3)0.71079 (14)0.00868 (10)0.0424 (4)
H410.478 (3)0.742 (2)0.0187 (13)0.064*
H420.503 (3)0.713 (2)0.0508 (9)0.064*
O500.0461 (4)0.90808 (16)0.08695 (13)0.0630 (6)
H510.106 (5)0.9606 (18)0.072 (2)0.095*
H520.086 (5)0.876 (2)0.1289 (13)0.095*
O600.1860 (3)0.88960 (16)0.05485 (12)0.0536 (5)
H610.257 (4)0.870 (3)0.0806 (15)0.080*
H620.210 (5)0.856 (2)0.0083 (7)0.080*
O700.2955 (5)0.9520 (2)0.0899 (2)0.1026 (10)
H710.236 (7)1.010 (2)0.100 (3)0.154*
H720.360 (7)0.946 (4)0.1331 (16)0.154*
O10.0793 (3)0.46163 (13)0.22701 (10)0.0473 (4)
H10.018 (3)0.4605 (14)0.1823 (4)0.057*
O20.1590 (3)0.39434 (13)0.11992 (9)0.0436 (4)
O30.3135 (3)0.23308 (14)0.15024 (10)0.0458 (4)
O40.1739 (3)0.22444 (16)0.84208 (10)0.0604 (6)
O50.3900 (3)0.29157 (14)0.76258 (11)0.0505 (5)
N10.1704 (3)0.12249 (15)0.45539 (11)0.0371 (4)
N20.1011 (3)0.12523 (16)0.52805 (11)0.0404 (5)
N30.2706 (3)0.21953 (15)0.77658 (11)0.0365 (4)
C10.1194 (3)0.30052 (17)0.25700 (12)0.0311 (5)
C20.0165 (3)0.37726 (17)0.28110 (14)0.0362 (5)
C30.0952 (4)0.36977 (18)0.36155 (14)0.0380 (5)
H30.18710.42100.37610.046*
C40.0366 (4)0.28584 (18)0.42029 (14)0.0386 (5)
H40.09020.28000.47430.046*
C50.1029 (3)0.21024 (17)0.39831 (13)0.0337 (5)
C60.1779 (3)0.21715 (17)0.31709 (13)0.0326 (5)
H60.26850.16530.30270.039*
C70.1589 (3)0.03711 (17)0.58710 (13)0.0342 (5)
C80.2876 (4)0.04755 (19)0.57064 (14)0.0391 (5)
H80.34620.04740.51790.047*
C90.3263 (3)0.13020 (18)0.63268 (13)0.0364 (5)
H90.41030.18700.62240.044*
C100.2389 (3)0.12844 (18)0.71104 (13)0.0367 (5)
C110.1150 (4)0.0458 (2)0.72882 (14)0.0453 (6)
H110.05750.04650.78180.054*
C120.0773 (4)0.0385 (2)0.66638 (15)0.0510 (7)
H120.00290.09630.67750.061*
C130.2054 (3)0.30891 (18)0.16969 (13)0.0356 (5)
O1A0.6032 (3)0.07174 (15)0.80581 (11)0.0539 (5)
H1A0.560 (4)0.0856 (15)0.85009 (16)0.065*
O2A0.4361 (3)0.18204 (14)0.90509 (10)0.0493 (5)
O3A0.2881 (3)0.33815 (14)0.86157 (10)0.0470 (4)
O4A0.2033 (3)0.66000 (15)0.15994 (10)0.0525 (5)
O5A0.0646 (3)0.75726 (14)0.24188 (11)0.0526 (5)
N1A0.3363 (3)0.38085 (16)0.55961 (11)0.0384 (5)
N2A0.3935 (3)0.36973 (16)0.48885 (11)0.0423 (5)
N3A0.1545 (3)0.67607 (16)0.22755 (12)0.0399 (5)
C1A0.4205 (3)0.23760 (17)0.76376 (13)0.0322 (5)
C2A0.5323 (4)0.14575 (18)0.74698 (14)0.0380 (5)
C3A0.5708 (4)0.1304 (2)0.66745 (16)0.0482 (6)
H3A0.63990.06910.65670.058*
C4A0.5078 (4)0.2049 (2)0.60525 (15)0.0461 (6)
H4A0.53490.19390.55240.055*
C5A0.4012 (3)0.29899 (17)0.62036 (13)0.0342 (5)
C6A0.3575 (3)0.31237 (18)0.70010 (14)0.0367 (5)
H6A0.28460.37270.71090.044*
C7A0.3266 (3)0.45134 (18)0.42707 (13)0.0362 (5)
C8A0.2047 (4)0.53881 (19)0.44037 (13)0.0408 (6)
H8A0.16220.54730.49320.049*
C9A0.1465 (4)0.61303 (19)0.37529 (14)0.0395 (5)
H9A0.06450.67140.38350.047*
C10A0.2138 (3)0.59775 (17)0.29782 (12)0.0322 (5)
C11A0.3370 (3)0.51270 (18)0.28285 (13)0.0370 (5)
H11A0.38110.50490.23000.044*
C12A0.3923 (4)0.43972 (19)0.34866 (14)0.0395 (5)
H12A0.47520.38180.34010.047*
C13A0.3759 (4)0.2550 (2)0.84887 (14)0.0389 (5)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Na10.0435 (6)0.0394 (5)0.0368 (5)0.0051 (4)0.0020 (4)0.0016 (4)
Na20.0520 (6)0.0389 (5)0.0562 (6)0.0043 (4)0.0044 (5)0.0123 (5)
O200.0436 (10)0.0475 (10)0.0345 (9)0.0057 (8)0.0055 (7)0.0112 (8)
O300.0524 (11)0.0462 (10)0.0351 (9)0.0039 (8)0.0060 (8)0.0076 (7)
O400.0480 (11)0.0491 (10)0.0319 (9)0.0103 (8)0.0040 (7)0.0103 (8)
O500.0938 (17)0.0480 (12)0.0484 (12)0.0096 (11)0.0190 (11)0.0041 (9)
O600.0611 (13)0.0582 (12)0.0440 (10)0.0114 (10)0.0044 (9)0.0149 (9)
O700.113 (3)0.0613 (16)0.129 (3)0.0298 (15)0.006 (2)0.0059 (16)
O10.0568 (12)0.0376 (9)0.0408 (10)0.0063 (8)0.0115 (8)0.0046 (8)
O20.0574 (11)0.0397 (9)0.0317 (8)0.0162 (8)0.0054 (8)0.0024 (7)
O30.0586 (12)0.0470 (10)0.0308 (8)0.0037 (9)0.0024 (8)0.0124 (7)
O40.0763 (14)0.0646 (12)0.0291 (9)0.0013 (11)0.0036 (9)0.0025 (8)
O50.0551 (12)0.0411 (10)0.0476 (10)0.0069 (9)0.0087 (9)0.0028 (8)
N10.0443 (12)0.0340 (10)0.0290 (10)0.0009 (9)0.0054 (8)0.0008 (8)
N20.0534 (13)0.0403 (11)0.0261 (10)0.0012 (9)0.0065 (9)0.0058 (8)
N30.0437 (12)0.0383 (11)0.0278 (10)0.0095 (9)0.0046 (8)0.0044 (8)
C10.0388 (13)0.0301 (11)0.0258 (10)0.0107 (9)0.0052 (9)0.0045 (8)
C20.0424 (14)0.0290 (11)0.0361 (12)0.0047 (10)0.0103 (10)0.0000 (9)
C30.0485 (14)0.0289 (11)0.0349 (12)0.0060 (10)0.0053 (10)0.0078 (9)
C40.0464 (14)0.0375 (12)0.0304 (11)0.0016 (11)0.0019 (10)0.0083 (10)
C50.0408 (13)0.0325 (11)0.0265 (11)0.0012 (10)0.0064 (9)0.0027 (9)
C60.0338 (12)0.0282 (11)0.0348 (12)0.0004 (9)0.0042 (9)0.0060 (9)
C70.0435 (14)0.0301 (11)0.0291 (11)0.0028 (10)0.0089 (10)0.0041 (9)
C80.0458 (14)0.0408 (13)0.0277 (11)0.0023 (11)0.0039 (10)0.0078 (10)
C90.0402 (13)0.0353 (12)0.0312 (11)0.0010 (10)0.0002 (10)0.0061 (9)
C100.0415 (14)0.0398 (13)0.0273 (11)0.0045 (10)0.0028 (10)0.0046 (9)
C110.0633 (18)0.0424 (13)0.0237 (11)0.0081 (12)0.0012 (11)0.0027 (10)
C120.0685 (19)0.0462 (15)0.0318 (12)0.0155 (13)0.0023 (12)0.0075 (11)
C130.0405 (13)0.0365 (12)0.0308 (11)0.0100 (10)0.0085 (10)0.0028 (10)
O1A0.0668 (13)0.0477 (11)0.0422 (10)0.0057 (9)0.0099 (9)0.0023 (8)
O2A0.0659 (13)0.0486 (10)0.0308 (9)0.0013 (9)0.0116 (8)0.0009 (8)
O3A0.0658 (12)0.0454 (10)0.0319 (9)0.0063 (9)0.0066 (8)0.0181 (7)
O4A0.0711 (13)0.0586 (11)0.0258 (9)0.0027 (10)0.0067 (8)0.0084 (8)
O5A0.0676 (13)0.0427 (10)0.0413 (10)0.0097 (9)0.0057 (9)0.0044 (8)
N1A0.0431 (12)0.0428 (11)0.0300 (10)0.0050 (9)0.0059 (8)0.0078 (8)
N2A0.0502 (13)0.0460 (12)0.0293 (10)0.0023 (10)0.0035 (9)0.0068 (9)
N3A0.0435 (12)0.0418 (11)0.0331 (11)0.0092 (9)0.0029 (9)0.0038 (9)
C1A0.0330 (12)0.0345 (12)0.0292 (11)0.0069 (9)0.0046 (9)0.0044 (9)
C2A0.0457 (14)0.0320 (12)0.0326 (12)0.0037 (10)0.0079 (10)0.0029 (9)
C3A0.0531 (16)0.0401 (14)0.0476 (15)0.0024 (12)0.0014 (12)0.0102 (11)
C4A0.0563 (17)0.0477 (14)0.0334 (13)0.0055 (12)0.0080 (11)0.0100 (11)
C5A0.0396 (13)0.0348 (12)0.0295 (11)0.0038 (10)0.0078 (9)0.0071 (9)
C6A0.0389 (13)0.0331 (12)0.0377 (12)0.0026 (10)0.0011 (10)0.0099 (10)
C7A0.0408 (13)0.0354 (12)0.0315 (11)0.0058 (10)0.0024 (10)0.0054 (9)
C8A0.0554 (16)0.0429 (13)0.0241 (11)0.0016 (11)0.0054 (10)0.0101 (10)
C9A0.0441 (14)0.0389 (13)0.0351 (12)0.0019 (11)0.0047 (10)0.0081 (10)
C10A0.0371 (13)0.0345 (11)0.0240 (10)0.0071 (9)0.0063 (9)0.0006 (9)
C11A0.0415 (13)0.0424 (13)0.0280 (11)0.0034 (10)0.0020 (10)0.0111 (10)
C12A0.0472 (15)0.0414 (13)0.0316 (12)0.0040 (11)0.0001 (10)0.0148 (10)
C13A0.0424 (14)0.0471 (14)0.0273 (11)0.0149 (11)0.0052 (10)0.0016 (10)
Geometric parameters (Å, º) top
Na1—O22.3474 (18)C3—H30.9300
Na1—O202.366 (2)C4—C51.392 (3)
Na1—O402.3743 (19)C4—H40.9300
Na1—O30i2.4211 (19)C5—C61.391 (3)
Na1—O302.474 (2)C6—H60.9300
Na1—O4A2.679 (2)C7—C121.388 (3)
Na1—Na1i3.3560 (19)C7—C81.406 (3)
Na1—Na23.4857 (14)C8—C91.368 (3)
Na2—O702.319 (3)C8—H80.9300
Na2—O502.372 (2)C9—C101.387 (3)
Na2—O402.420 (2)C9—H90.9300
Na2—O202.428 (2)C10—C111.374 (3)
Na2—O602.481 (3)C11—C121.384 (3)
Na2—O4ii2.491 (2)C11—H110.9300
Na2—H212.67 (3)C12—H120.9300
Na2—H622.42 (3)O1A—C2A1.347 (3)
O20—H210.821 (3)O1A—H1A0.8200 (10)
O20—H220.820 (3)O2A—C13A1.281 (3)
O30—Na1i2.4212 (19)O3A—C13A1.234 (3)
O30—H310.820 (3)O4A—N3A1.207 (2)
O30—H320.820 (3)O5A—N3A1.226 (3)
O40—H410.820 (3)N1A—N2A1.245 (3)
O40—H420.820 (3)N1A—C5A1.405 (3)
O50—H510.821 (3)N2A—C7A1.420 (3)
O50—H520.821 (3)N3A—C10A1.475 (3)
O60—H610.821 (3)C1A—C6A1.384 (3)
O60—H620.820 (3)C1A—C2A1.421 (3)
O70—H710.821 (3)C1A—C13A1.496 (3)
O70—H720.821 (3)C2A—C3A1.393 (4)
O1—C21.352 (3)C3A—C4A1.365 (4)
O1—H10.8201 (10)C3A—H3A0.9300
O2—C131.286 (3)C4A—C5A1.421 (3)
O3—C131.257 (3)C4A—H4A0.9300
O4—N31.212 (3)C5A—C6A1.390 (3)
O4—Na2iii2.491 (2)C6A—H6A0.9300
O5—N31.236 (3)C7A—C12A1.380 (3)
N1—N21.266 (3)C7A—C8A1.394 (3)
N1—C51.420 (3)C8A—C9A1.384 (3)
N2—C71.419 (3)C8A—H8A0.9300
N3—C101.462 (3)C9A—C10A1.382 (3)
C1—C61.394 (3)C9A—H9A0.9300
C1—C21.399 (3)C10A—C11A1.381 (3)
C1—C131.503 (3)C11A—C12A1.379 (3)
C2—C31.385 (3)C11A—H11A0.9300
C3—C41.384 (3)C12A—H12A0.9300
O2—Na1—O2094.62 (7)C13—O2—Na1139.59 (16)
O2—Na1—O40168.45 (7)N3—O4—Na2iii149.03 (19)
O20—Na1—O4087.33 (7)N2—N1—C5112.87 (19)
O2—Na1—O30i106.34 (7)N1—N2—C7114.96 (19)
O20—Na1—O30i97.26 (7)O4—N3—O5121.8 (2)
O40—Na1—O30i84.66 (7)O4—N3—C10119.2 (2)
O2—Na1—O3091.35 (7)O5—N3—C10118.96 (18)
O20—Na1—O30165.76 (7)C6—C1—C2117.82 (19)
O40—Na1—O3084.32 (7)C6—C1—C13120.6 (2)
O30i—Na1—O3093.44 (6)C2—C1—C13121.53 (19)
O2—Na1—O4A95.53 (7)O1—C2—C3116.7 (2)
O20—Na1—O4A76.60 (6)O1—C2—C1121.8 (2)
O40—Na1—O4A73.82 (6)C3—C2—C1121.5 (2)
O30i—Na1—O4A157.77 (7)C4—C3—C2119.8 (2)
O30—Na1—O4A89.97 (7)C4—C3—H3120.1
O2—Na1—Na1i102.72 (6)C2—C3—H3120.1
O20—Na1—Na1i143.67 (6)C3—C4—C5119.8 (2)
O40—Na1—Na1i81.95 (6)C3—C4—H4120.1
O30i—Na1—Na1i47.38 (5)C5—C4—H4120.1
O30—Na1—Na1i46.07 (5)C6—C5—C4119.9 (2)
O4A—Na1—Na1i131.87 (7)C6—C5—N1117.2 (2)
O2—Na1—Na2135.26 (6)C4—C5—N1122.8 (2)
O20—Na1—Na244.06 (5)C5—C6—C1121.0 (2)
O40—Na1—Na243.88 (5)C5—C6—H6119.5
O30i—Na1—Na297.02 (5)C1—C6—H6119.5
O30—Na1—Na2125.25 (6)C12—C7—C8120.0 (2)
O4A—Na1—Na263.55 (5)C12—C7—N2114.8 (2)
Na1i—Na1—Na2120.90 (4)C8—C7—N2125.2 (2)
O70—Na2—O5086.84 (11)C9—C8—C7119.6 (2)
O70—Na2—O4086.28 (11)C9—C8—H8120.2
O50—Na2—O40111.51 (8)C7—C8—H8120.2
O70—Na2—O20159.68 (11)C8—C9—C10119.3 (2)
O50—Na2—O20113.44 (8)C8—C9—H9120.3
O40—Na2—O2084.92 (7)C10—C9—H9120.3
O70—Na2—O6096.60 (11)C11—C10—C9122.2 (2)
O50—Na2—O6082.84 (8)C11—C10—N3118.3 (2)
O40—Na2—O60165.54 (8)C9—C10—N3119.5 (2)
O20—Na2—O6087.70 (7)C10—C11—C12118.7 (2)
O70—Na2—O4ii78.88 (11)C10—C11—H11120.7
O50—Na2—O4ii158.56 (8)C12—C11—H11120.7
O40—Na2—O4ii83.66 (7)C11—C12—C7120.2 (2)
O20—Na2—O4ii81.96 (7)C11—C12—H12119.9
O60—Na2—O4ii83.01 (7)C7—C12—H12119.9
O70—Na2—Na1128.35 (10)O3—C13—O2124.9 (2)
O50—Na2—Na1115.65 (6)O3—C13—C1118.8 (2)
O40—Na2—Na142.85 (5)O2—C13—C1116.3 (2)
O20—Na2—Na142.65 (5)C2A—O1A—H1A108.9 (14)
O60—Na2—Na1130.21 (6)N3A—O4A—Na1157.52 (16)
O4ii—Na2—Na185.78 (6)N2A—N1A—C5A114.6 (2)
O70—Na2—H21174.1 (5)N1A—N2A—C7A115.0 (2)
O50—Na2—H2196.7 (3)O4A—N3A—O5A123.8 (2)
O40—Na2—H2196.7 (5)O4A—N3A—C10A119.3 (2)
O20—Na2—H2117.7 (3)O5A—N3A—C10A116.80 (19)
O60—Na2—H2179.3 (5)C6A—C1A—C2A119.2 (2)
O4ii—Na2—H2196.4 (3)C6A—C1A—C13A120.2 (2)
Na1—Na2—H2154.0 (5)C2A—C1A—C13A120.5 (2)
O70—Na2—H62112.2 (5)O1A—C2A—C3A118.2 (2)
O50—Na2—H6273.5 (7)O1A—C2A—C1A122.1 (2)
O40—Na2—H62161.3 (6)C3A—C2A—C1A119.7 (2)
O20—Na2—H6276.8 (6)C4A—C3A—C2A120.4 (2)
O60—Na2—H6219.22 (10)C4A—C3A—H3A119.8
O4ii—Na2—H6297.0 (5)C2A—C3A—H3A119.8
Na1—Na2—H62118.5 (6)C3A—C4A—C5A120.8 (2)
H21—Na2—H6264.7 (7)C3A—C4A—H4A119.6
Na1—O20—Na293.28 (7)C5A—C4A—H4A119.6
Na1—O20—H21122.3 (19)C6A—C5A—N1A117.0 (2)
Na2—O20—H2198 (2)C6A—C5A—C4A118.7 (2)
Na1—O20—H22122.5 (19)N1A—C5A—C4A124.3 (2)
Na2—O20—H22112 (2)C1A—C6A—C5A121.2 (2)
H21—O20—H22105 (2)C1A—C6A—H6A119.4
Na1i—O30—Na186.56 (6)C5A—C6A—H6A119.4
Na1i—O30—H31116 (2)C12A—C7A—C8A119.8 (2)
Na1—O30—H31114 (2)C12A—C7A—N2A114.9 (2)
Na1i—O30—H32104 (2)C8A—C7A—N2A125.2 (2)
Na1—O30—H32130 (2)C9A—C8A—C7A120.3 (2)
H31—O30—H32105 (3)C9A—C8A—H8A119.9
Na1—O40—Na293.27 (7)C7A—C8A—H8A119.9
Na1—O40—H41124 (2)C10A—C9A—C8A118.0 (2)
Na2—O40—H41102 (2)C10A—C9A—H9A121.0
Na1—O40—H42115 (2)C8A—C9A—H9A121.0
Na2—O40—H42117 (2)C9A—C10A—C11A122.9 (2)
H41—O40—H42105 (3)C9A—C10A—N3A119.0 (2)
Na2—O50—H51106 (3)C11A—C10A—N3A118.11 (19)
Na2—O50—H52111 (3)C12A—C11A—C10A118.0 (2)
H51—O50—H52105 (3)C12A—C11A—H11A121.0
Na2—O60—H61130 (3)C10A—C11A—H11A121.0
Na2—O60—H6276 (2)C11A—C12A—C7A121.0 (2)
H61—O60—H62105 (3)C11A—C12A—H12A119.5
Na2—O70—H71117 (4)C7A—C12A—H12A119.5
Na2—O70—H72118 (4)O3A—C13A—O2A123.4 (2)
H71—O70—H72105 (5)O3A—C13A—C1A119.5 (2)
C2—O1—H1108.3 (13)O2A—C13A—C1A117.1 (2)
O2—Na1—Na2—O70176.45 (14)C6—C1—C2—C31.8 (3)
O20—Na1—Na2—O70154.96 (15)C13—C1—C2—C3179.7 (2)
O40—Na1—Na2—O7012.97 (14)O1—C2—C3—C4179.6 (2)
O30i—Na1—Na2—O7061.76 (14)C1—C2—C3—C41.3 (4)
O30—Na1—Na2—O7037.51 (15)C2—C3—C4—C50.8 (4)
O4A—Na1—Na2—O70106.88 (14)C3—C4—C5—C62.3 (4)
Na1i—Na1—Na2—O7017.94 (15)C3—C4—C5—N1179.6 (2)
O2—Na1—Na2—O5068.87 (11)N2—N1—C5—C6176.9 (2)
O20—Na1—Na2—O5097.46 (10)N2—N1—C5—C45.0 (3)
O40—Na1—Na2—O5094.61 (10)C4—C5—C6—C11.7 (4)
O30i—Na1—Na2—O50169.34 (9)N1—C5—C6—C1179.9 (2)
O30—Na1—Na2—O5070.07 (10)C2—C1—C6—C50.3 (3)
O4A—Na1—Na2—O500.69 (9)C13—C1—C6—C5178.2 (2)
Na1i—Na1—Na2—O50125.52 (9)N1—N2—C7—C12177.8 (2)
O2—Na1—Na2—O40163.48 (10)N1—N2—C7—C82.1 (4)
O20—Na1—Na2—O40167.93 (9)C12—C7—C8—C92.5 (4)
O30i—Na1—Na2—O4074.73 (8)N2—C7—C8—C9177.4 (2)
O30—Na1—Na2—O4024.54 (8)C7—C8—C9—C100.6 (4)
O4A—Na1—Na2—O4093.92 (8)C8—C9—C10—C110.4 (4)
Na1i—Na1—Na2—O4030.91 (7)C8—C9—C10—N3176.2 (2)
O2—Na1—Na2—O2028.60 (10)O4—N3—C10—C117.3 (3)
O40—Na1—Na2—O20167.93 (9)O5—N3—C10—C11175.7 (2)
O30i—Na1—Na2—O2093.20 (8)O4—N3—C10—C9169.4 (2)
O30—Na1—Na2—O20167.53 (9)O5—N3—C10—C97.6 (3)
O4A—Na1—Na2—O2098.16 (8)C9—C10—C11—C120.4 (4)
Na1i—Na1—Na2—O20137.02 (8)N3—C10—C11—C12177.0 (3)
O2—Na1—Na2—O6034.14 (12)C10—C11—C12—C72.2 (4)
O20—Na1—Na2—O605.54 (9)C8—C7—C12—C113.3 (4)
O40—Na1—Na2—O60162.38 (10)N2—C7—C12—C11176.6 (3)
O30i—Na1—Na2—O6087.65 (9)Na1—O2—C13—O371.7 (3)
O30—Na1—Na2—O60173.08 (9)Na1—O2—C13—C1109.3 (2)
O4A—Na1—Na2—O60103.70 (9)C6—C1—C13—O38.7 (3)
Na1i—Na1—Na2—O60131.48 (8)C2—C1—C13—O3173.5 (2)
O2—Na1—Na2—O4ii111.30 (10)C6—C1—C13—O2172.3 (2)
O20—Na1—Na2—O4ii82.71 (8)C2—C1—C13—O25.6 (3)
O40—Na1—Na2—O4ii85.22 (8)O2—Na1—O4A—N3A15.2 (5)
O30i—Na1—Na2—O4ii10.49 (8)O20—Na1—O4A—N3A108.6 (5)
O30—Na1—Na2—O4ii109.76 (8)O40—Na1—O4A—N3A160.3 (5)
O4A—Na1—Na2—O4ii179.14 (8)O30i—Na1—O4A—N3A175.2 (4)
Na1i—Na1—Na2—O4ii54.31 (8)O30—Na1—O4A—N3A76.2 (5)
O2—Na1—O20—Na2160.25 (7)Na1i—Na1—O4A—N3A97.4 (5)
O40—Na1—O20—Na28.34 (6)Na2—Na1—O4A—N3A153.7 (5)
O30i—Na1—O20—Na292.61 (7)C5A—N1A—N2A—C7A179.2 (2)
O30—Na1—O20—Na245.8 (3)Na1—O4A—N3A—O5A148.3 (3)
O4A—Na1—O20—Na265.65 (6)Na1—O4A—N3A—C10A35.5 (6)
Na1i—Na1—O20—Na280.88 (12)C6A—C1A—C2A—O1A177.8 (2)
O70—Na2—O20—Na172.9 (3)C13A—C1A—C2A—O1A0.5 (4)
O50—Na2—O20—Na1103.05 (9)C6A—C1A—C2A—C3A2.4 (4)
O40—Na2—O20—Na18.21 (6)C13A—C1A—C2A—C3A179.4 (2)
O60—Na2—O20—Na1175.77 (7)O1A—C2A—C3A—C4A177.7 (3)
O4ii—Na2—O20—Na192.50 (7)C1A—C2A—C3A—C4A2.5 (4)
O2—Na1—O30—Na1i106.46 (7)C2A—C3A—C4A—C5A0.3 (4)
O20—Na1—O30—Na1i138.7 (3)N2A—N1A—C5A—C6A173.7 (2)
O40—Na1—O30—Na1i84.28 (6)N2A—N1A—C5A—C4A6.1 (3)
O30i—Na1—O30—Na1i0.0C3A—C4A—C5A—C6A1.9 (4)
O4A—Na1—O30—Na1i158.02 (7)C3A—C4A—C5A—N1A177.9 (3)
Na2—Na1—O30—Na1i101.09 (7)C2A—C1A—C6A—C5A0.2 (4)
O2—Na1—O40—Na291.7 (4)C13A—C1A—C6A—C5A178.4 (2)
O20—Na1—O40—Na28.37 (6)N1A—C5A—C6A—C1A177.9 (2)
O30i—Na1—O40—Na2105.92 (7)C4A—C5A—C6A—C1A1.9 (4)
O30—Na1—O40—Na2160.07 (7)N1A—N2A—C7A—C12A179.1 (2)
O4A—Na1—O40—Na268.45 (7)N1A—N2A—C7A—C8A0.6 (4)
Na1i—Na1—O40—Na2153.57 (6)C12A—C7A—C8A—C9A1.2 (4)
O70—Na2—O40—Na1169.84 (11)N2A—C7A—C8A—C9A179.1 (2)
O50—Na2—O40—Na1105.03 (8)C7A—C8A—C9A—C10A0.4 (4)
O20—Na2—O40—Na18.18 (6)C8A—C9A—C10A—C11A0.6 (4)
O60—Na2—O40—Na167.7 (3)C8A—C9A—C10A—N3A179.7 (2)
O4ii—Na2—O40—Na190.63 (7)O4A—N3A—C10A—C9A175.5 (2)
O20—Na1—O2—C13165.9 (2)O5A—N3A—C10A—C9A8.1 (3)
O40—Na1—O2—C1366.6 (5)O4A—N3A—C10A—C11A5.3 (3)
O30i—Na1—O2—C1395.1 (2)O5A—N3A—C10A—C11A171.1 (2)
O30—Na1—O2—C131.2 (2)C9A—C10A—C11A—C12A0.8 (4)
O4A—Na1—O2—C1388.9 (2)N3A—C10A—C11A—C12A179.9 (2)
Na1i—Na1—O2—C1346.2 (2)C10A—C11A—C12A—C7A0.0 (4)
Na2—Na1—O2—C13146.4 (2)C8A—C7A—C12A—C11A1.0 (4)
C5—N1—N2—C7177.7 (2)N2A—C7A—C12A—C11A179.3 (2)
Na2iii—O4—N3—O590.3 (4)C6A—C1A—C13A—O3A2.5 (4)
Na2iii—O4—N3—C1092.8 (3)C2A—C1A—C13A—O3A175.7 (2)
C6—C1—C2—O1179.0 (2)C6A—C1A—C13A—O2A179.0 (2)
C13—C1—C2—O11.1 (3)C2A—C1A—C13A—O2A2.8 (3)
Symmetry codes: (i) x+1, y+1, z; (ii) x, y+1, z1; (iii) x, y1, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O20.82 (1)1.80 (2)2.534 (3)149 (2)
O1A—H1A···O2A0.82 (1)1.80 (2)2.532 (3)147 (2)
O20—H21···O3Aiv0.82 (2)1.93 (2)2.750 (2)174 (3)
O20—H22···O2v0.82 (2)2.04 (2)2.862 (2)173 (2)
O30—H31···O5vi0.82 (2)2.32 (2)3.135 (3)175 (2)
O30—H32···O3Avii0.82 (2)2.14 (3)2.823 (3)141 (2)
O40—H41···O2Avii0.82 (2)2.00 (2)2.819 (3)172 (2)
O40—H42···O3i0.82 (2)2.02 (2)2.813 (3)161 (3)
O50—H51···O60viii0.82 (3)2.04 (2)2.838 (3)163 (3)
O50—H52···O5A0.82 (3)2.18 (2)2.931 (3)152 (3)
O60—H61···O3v0.82 (3)2.09 (3)2.828 (3)150 (3)
O60—H62···O2Aiv0.82 (2)2.21 (3)2.917 (3)145 (3)
O70—H71···O50viii0.82 (4)2.19 (5)2.892 (4)144 (4)
O70—H72···O1Aii0.82 (3)2.48 (5)2.972 (4)119 (4)
C12—H12···O5Aiv0.932.553.358 (3)146
C12A—H12A···O5vi0.932.343.125 (3)141
Symmetry codes: (i) x+1, y+1, z; (ii) x, y+1, z1; (iv) x, y+1, z+1; (v) x, y+1, z; (vi) x+1, y, z+1; (vii) x+1, y+1, z+1; (viii) x, y+2, z.
Selected interatomic distances (Å) in (I)–(III) compared with closely related structures top
Distance(I)(II)(III)(III)AdACEFIZFUGYIPEXIZUH1eEXIZUH2
O1—C21.3400 (17)1.350 (3)1.352 (3)1.347 (3)1.354 (3)1.355 (2)1.350 (4)1.362 (4)
C1—C21.403 (2)1.419 (3)1.399 (2)1.421 (3)1.401 (3)1.403 (3)1.396 (5)1.397 (4)
C1—C131.4653 (19)1.500 (3)1.503 (3)1.496 (3)1.454 (3)1.462 (3)1.479 (4)1.482 (5)
C5—N11.4213 (19)1.421 (3)1.420 (3)1.405 (3)1.451 (3)1.432 (2)1.413 (4)1.421 (4)
N1—N21.2519 (19)1.249 (3)1.266 (3)1.245 (3)1.246 (3)1.260 (2)1.242 (3)1.245 (3)
N2—C71.4256 (19)1.428 (3)1.419 (3)1.420 (3)1.431 (3)1.424 (2)1.431 (4)1.437 (4)
O2—C131.2290 (17)1.265 (3)1.286 (3)1.281 (3)1.240 (2)1.241 (2)1.229 (4)1.228 (4)
O3—C131.3081 (19)1.246 (3)1.257 (3)1.234 (3)1.313 (2)1.311 (2)1.300 (4)1.290 (4)
O1···O22.619 (2)2.524 (3)2.534 (3)2.532 (2)2.630 (2)2.631 (2)2.574 (3)2.605 (3)
Notes: (a) 5-(phenyldiazenyl)salicylic acid (Saikia et al., 2012); (b) 5-(4-methoxyphenyldiazenyl)salicylic acid (Basu Baul et al., 2000); (c) the molecular complex of 5-(phenyldiazenyl)salicylic acid with dimethylpyrazole (Xu et al.; 2011); (d) the second anion in (III) is labelled with the letter `A'; (e) the structure contains two symmetry-independent molecules.
Hydrogen-bonding geometry (Å, °) in (I)–(III) top
D—H···AD—HH···AD···AD—H···A
(I)
O1—H1···O20.820 (14)1.895 (14)2.6189 (16)146.8 (14)
O1—H1···O4a0.820 (14)2.420 (14)3.0461 (18)134.0 (13)
O3—H13···O2b0.820 (13)1.847 (14)2.6651 (16)176.4 (14)
C4—H4···O5c0.932.383.202 (2)147
(II)
O1—H1···O20.82 (2)1.78 (2)2.524 (3)151 (2)
N3—H21···O3d0.89 (2)1.99 (2)2.788 (3)150 (2)
N3—H22···O2e0.89 (2)1.91 (2)2.779 (3)164 (2)
N3—H23···O10.89 (2)2.38 (2)3.052 (3)132 (2)
N3—H24···O3f0.89 (2)1.91 (2)2.799 (3)172 (2)
(III)
O1—H1···O20.820 (11)1.796 (17)2.534 (3)148.9 (16)
O1A—H1A···O2A0.820 (10)1.804 (18)2.532 (3)147.3 (17)
O20—H21···O3Ag0.82 (2)1.93 (2)2.750 (2)174 (3)
O20—H22···O2h0.82 (2)2.04 (2)2.862 (2)173 (2)
O30—H31···O5i0.82 (2)2.32 (2)3.135 (3)175 (2)
O30—H32···O3Aj0.82 (2)2.14 (3)2.823 (3)141 (2)
O40—H41···O2Aj0.82 (2)2.00 (2)2.819 (3)172 (2)
O40—H42···O3k0.82 (2)2.02 (2)2.813 (3)161 (3)
O50—H51···O60l0.82 (3)2.04 (2)2.838 (3)163 (3)
O50—H52···O5A0.82 (3)2.18 (2)2.931 (3)152 (3)
O60—H61···O3h0.82 (3)2.09 (3)2.828 (3)150 (3)
O60—H62···O2Ag0.82 (2)2.21 (2)2.917 (3)145 (3)
O70—H71···O50l0.82 (4)2.19 (5)2.892 (4)144 (4)
O70—H72···O1Am0.82 (3)2.48 (5)2.972 (4)119 (4)
C12—H12···O5Ag0.932.553.358 (3)146
C12A—H12A···O5i0.932.343.125 (3)141
Symmetry codes: (a) x+2, -y+1/2, z-1/2; (b) -x+3, -y+1, -z; (c) -x, y-1/2, -z+1/2; (d) x-1, y, z+1; (e) x-1, y, z; (f) -x+1, -y, -z+2; (g) -x, -y+1, -z+1; (h) -x, -y+1, -z; (i) -x+1, -y, -z+1; (j) -x+1, -y+1, -z+1; (k) -x+1, -y+1, -z; (l) -x, -y+2, -z; (m) x, y+1, z-1.
Results of DFT calculations for an isolated molecule of 2-hydroxy-5-(phenyldiazenyl)benzoic acid, for the same molecule placed in a polarizable continuum with parameters simulating acetone, for two molecules bound as a dimer by a pair of hydrogen bonds between the carboxylate groups and for the anion of 2-hydroxy-5-(phenyldiazenyl)benzoic acid placed in a polarizable continuum with parameters simulating acetone top
E (anti) (Hartree)E (syn) (Hartree)E (syn) – E (anti) (kJ mol-1)
Isolated molecule-836.78754-836.786662.3
Molecule in a polarizable continuum-836.79481-836.794191.6
Hydrogen-bonded dimer-1673.60221-1673.600344.9
Anion in a polarizable continuum-836.32959-836.328991.6
 

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