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In the crystal structure of the title compound, C7H5N3O6·H2O, O—H...O and N—H...O hydrogen bonds result in the formation of a supra­molecular network structure.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807039712/at2370sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807039712/at2370Isup2.hkl
Contains datablock I

CCDC reference: 1196852

Key indicators

  • Single-crystal X-ray study
  • T = 273 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.047
  • wR factor = 0.143
  • Data-to-parameter ratio = 11.1

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT230_ALERT_2_B Hirshfeld Test Diff for N3 - C7 .. 13.08 su PLAT430_ALERT_2_B Short Inter D...A Contact O2 .. O2 .. 2.64 Ang.
Alert level C PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.98 PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.31
Alert level G PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 9
0 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 3 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Comment top

In the synthesis of crystal structures by design, the assembly of molecular units in predefined arrangements is a key goal (Desiraju, 1995, 1997; Braga et al., 1998). Due to hydrogen-bonding interactions are of critical importance in biological systems, organic materials and coordination chemistry. Hydrogen-bonding is currently the best tools in achieving this goal. (Zaworotko, 1997; Braga & Grepioni, 2000). Supramolecular architectures are of considerable contemporary interest by virtue of their potential applications in various fields. (Moulton & Zaworotko, 2001; Pan et al., 2001; Ma et al., 2001; Prior & Rosseinsky, 2001). We originally attempted to synthesize complexes featuring La metal chains by reaction of the lanthanum(III) ion with 2-hydroxy-3,5-dinitrobenzamide ligand. Unfortunately, we obtained only the title compound, (I), (Fig. 1).

In the title molecule (I), all bond lengths and angles are within normal ranges (Allen et al., 1987). In the title complex (I), contains one 2-hydroxy-3,5-dinitrobenzamide molecule and one uncoordinated water molecule. The uncoordinated water molecule interacts with nearby nitro, hydroxy and amino groups of the 2-hydroxy-3,5-dinitrobenzamide ligands by way of O—H···O and N—H···O hydrogen bonds, forming a supramolecular network structure (Fig. 2 and Table 1).

Related literature top

For related literature, see: Allen et al. (1987); Braga et al. (1998); Braga & Grepioni (2000); Desiraju (1995, 1997); Ma et al. (2001); Moulton & Zaworotko (2001); Pan et al. (2001); Prior & Rosseinsky (2001); Zaworotko (1997).

Experimental top

Crystals of the title compound (I) were synthesized using hydrothermal method in a 23 ml Teflon-lined Parr bomb, which was then sealed. Lanthanum (III) nitrate hexahydrate (216.4 mg, 0.5 mmol), 2-hydroxy-3,5-dinitrobenzamide (227.2 mg, 1 mmol) and distilled water (5 g) were placed into the bomb and sealed. The bomb was then heated under autogenous pressure up to 443 K over the course of 7 d and allowed to cool at room temperature for 24 h. Upon opening the bomb, a clear colourless solution was decanted from small colourless crystals. These crystals were washed with distilled water followed by ethanol, and allowed to air-dry at room temperature.

Refinement top

The H atoms of the water molecule and the amino group were located from difference Fourier syntheses and refined with restraints to the O—H distances and the H—O—H angles. The remaining H atoms were positioned geometrically, with O—H = 0.82 Å for the water H atoms and C—H = 0.93 Å for aromatic H atoms, and constrained to ride on their parent atoms, with Uiso(H) = xUeq(C, O), where x = 1.2 for aromatic H atoms and x = 1.5 for the water H atoms.

Structure description top

In the synthesis of crystal structures by design, the assembly of molecular units in predefined arrangements is a key goal (Desiraju, 1995, 1997; Braga et al., 1998). Due to hydrogen-bonding interactions are of critical importance in biological systems, organic materials and coordination chemistry. Hydrogen-bonding is currently the best tools in achieving this goal. (Zaworotko, 1997; Braga & Grepioni, 2000). Supramolecular architectures are of considerable contemporary interest by virtue of their potential applications in various fields. (Moulton & Zaworotko, 2001; Pan et al., 2001; Ma et al., 2001; Prior & Rosseinsky, 2001). We originally attempted to synthesize complexes featuring La metal chains by reaction of the lanthanum(III) ion with 2-hydroxy-3,5-dinitrobenzamide ligand. Unfortunately, we obtained only the title compound, (I), (Fig. 1).

In the title molecule (I), all bond lengths and angles are within normal ranges (Allen et al., 1987). In the title complex (I), contains one 2-hydroxy-3,5-dinitrobenzamide molecule and one uncoordinated water molecule. The uncoordinated water molecule interacts with nearby nitro, hydroxy and amino groups of the 2-hydroxy-3,5-dinitrobenzamide ligands by way of O—H···O and N—H···O hydrogen bonds, forming a supramolecular network structure (Fig. 2 and Table 1).

For related literature, see: Allen et al. (1987); Braga et al. (1998); Braga & Grepioni (2000); Desiraju (1995, 1997); Ma et al. (2001); Moulton & Zaworotko (2001); Pan et al. (2001); Prior & Rosseinsky (2001); Zaworotko (1997).

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Siemens, 1996); software used to prepare material for publication: SHELXTL (Siemens, 1996).

Figures top
[Figure 1] Fig. 1. The structure of the title molecule (I), with the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
[Figure 2] Fig. 2. A view of the packing diagram of the title compound (I). Hydrogen bonds are shown as dashed lines.
2-Hydroxy-3,5-dinitrobenzamide monohydrate top
Crystal data top
C7H5N3O6·H2OF(000) = 1008
Mr = 245.16Dx = 1.658 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 1511 reflections
a = 25.4442 (14) Åθ = 3.1–26.8°
b = 6.663 (3) ŵ = 0.15 mm1
c = 12.486 (2) ÅT = 273 K
β = 111.882 (7)°Prism, colourless
V = 1964.2 (9) Å30.24 × 0.15 × 0.14 mm
Z = 8
Data collection top
Bruker APEXII area-detector
diffractometer
1891 independent reflections
Radiation source: fine-focus sealed tube979 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.030
φ and ω scansθmax = 26.0°, θmin = 3.2°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 3131
Tmin = 0.965, Tmax = 0.979k = 88
6123 measured reflectionsl = 1515
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) = 0.143H atoms treated by a mixture of independent and constrained refinement
S = 1.02 w = 1/[σ2(Fo2) + (0.0754P)2 + 0.002P]
where P = (Fo2 + 2Fc2)/3
1891 reflections(Δ/σ)max < 0.001
171 parametersΔρmax = 0.22 e Å3
9 restraintsΔρmin = 0.25 e Å3
Crystal data top
C7H5N3O6·H2OV = 1964.2 (9) Å3
Mr = 245.16Z = 8
Monoclinic, C2/cMo Kα radiation
a = 25.4442 (14) ŵ = 0.15 mm1
b = 6.663 (3) ÅT = 273 K
c = 12.486 (2) Å0.24 × 0.15 × 0.14 mm
β = 111.882 (7)°
Data collection top
Bruker APEXII area-detector
diffractometer
1891 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
979 reflections with I > 2σ(I)
Tmin = 0.965, Tmax = 0.979Rint = 0.030
6123 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0479 restraints
wR(F2) = 0.143H atoms treated by a mixture of independent and constrained refinement
S = 1.02Δρmax = 0.22 e Å3
1891 reflectionsΔρmin = 0.25 e Å3
171 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
O10.40219 (7)0.2100 (3)0.72887 (14)0.0733 (6)
H10.43630.22380.74450.110*
O20.50775 (8)0.2170 (4)0.86062 (17)0.1046 (9)
O30.29250 (7)0.1318 (3)0.63098 (15)0.0808 (6)
O40.24220 (7)0.3057 (3)0.70399 (16)0.0788 (6)
O50.30605 (8)0.3711 (3)1.11219 (16)0.0851 (7)
O60.39244 (10)0.3009 (4)1.21820 (18)0.0977 (8)
O70.63147 (8)0.2289 (3)0.0270 (2)0.0747 (6)
N10.28690 (9)0.2263 (3)0.70936 (18)0.0609 (6)
N20.35423 (10)0.3195 (3)1.12494 (19)0.0648 (6)
N30.53256 (8)0.2535 (3)1.04702 (17)0.0518 (5)
C10.43553 (9)0.2454 (4)0.9348 (2)0.0540 (6)
C20.39114 (10)0.2307 (4)0.8245 (2)0.0538 (6)
C30.33530 (10)0.2444 (4)0.8195 (2)0.0521 (6)
C40.32289 (10)0.2747 (4)0.91675 (19)0.0534 (6)
H50.28560.28840.91130.064*
C50.36667 (10)0.2842 (4)1.0214 (2)0.0534 (6)
C60.42273 (10)0.2690 (4)1.0317 (2)0.0549 (6)
H70.45160.27491.10420.066*
C70.49510 (11)0.2384 (4)0.9443 (2)0.0635 (7)
H3A0.5613 (8)0.242 (4)1.038 (2)0.076 (9)*
H7A0.6382 (15)0.218 (6)0.0344 (16)0.153 (18)*
H7B0.6661 (4)0.224 (6)0.072 (2)0.161 (19)*
H3B0.536 (2)0.223 (9)1.114 (2)0.13 (4)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0388 (10)0.1292 (17)0.0523 (11)0.0006 (10)0.0174 (8)0.0027 (10)
O20.0408 (11)0.213 (3)0.0625 (14)0.0029 (12)0.0218 (10)0.0000 (13)
O30.0550 (11)0.1232 (17)0.0598 (11)0.0076 (11)0.0163 (9)0.0159 (11)
O40.0354 (11)0.1272 (17)0.0682 (12)0.0107 (10)0.0127 (9)0.0074 (11)
O50.0597 (13)0.1248 (17)0.0806 (13)0.0052 (12)0.0376 (11)0.0096 (12)
O60.0746 (16)0.159 (2)0.0555 (13)0.0147 (13)0.0196 (12)0.0044 (13)
O70.0418 (11)0.1017 (16)0.0737 (13)0.0016 (10)0.0136 (10)0.0045 (11)
N10.0395 (13)0.0892 (17)0.0517 (13)0.0033 (11)0.0145 (10)0.0049 (11)
N20.0549 (15)0.0851 (17)0.0576 (14)0.0006 (12)0.0246 (13)0.0045 (11)
N30.0216 (10)0.0865 (16)0.0402 (12)0.0005 (10)0.0034 (9)0.0003 (9)
C10.0365 (14)0.0718 (17)0.0510 (15)0.0003 (11)0.0133 (12)0.0012 (12)
C20.0412 (14)0.0726 (17)0.0489 (14)0.0017 (12)0.0183 (12)0.0004 (11)
C30.0395 (14)0.0650 (16)0.0476 (14)0.0005 (11)0.0112 (11)0.0044 (11)
C40.0404 (14)0.0650 (16)0.0559 (15)0.0011 (11)0.0192 (12)0.0045 (11)
C50.0476 (15)0.0633 (16)0.0518 (14)0.0025 (11)0.0212 (12)0.0001 (11)
C60.0404 (13)0.0707 (17)0.0493 (14)0.0014 (11)0.0117 (11)0.0008 (11)
C70.0450 (15)0.087 (2)0.0602 (17)0.0008 (13)0.0212 (14)0.0051 (13)
Geometric parameters (Å, º) top
O1—C21.331 (3)N3—H3A0.787 (13)
O2—C71.211 (3)N3—H3B0.83 (3)
O3—N11.216 (3)C1—C61.374 (3)
O4—N11.233 (3)C1—C21.422 (3)
O5—N21.225 (3)C1—C71.476 (3)
O6—N21.214 (3)C2—C31.402 (3)
N1—C31.470 (3)C3—C41.378 (3)
N2—C51.461 (3)C4—C51.366 (3)
N3—C71.285 (3)C4—H50.9300
O1—H10.8200C5—C61.387 (3)
O7—H7A0.85 (3)C6—H70.9300
O7—H7B0.851 (18)
O2—C7—N3122.2 (2)C2—C1—C7119.8 (2)
O2—C7—C1122.0 (2)O1—C2—C3121.1 (2)
N3—C7—C1115.8 (2)O1—C2—C1121.2 (2)
O3—N1—O4124.1 (2)C3—C2—C1117.7 (2)
O3—N1—C3119.2 (2)C4—C3—C2122.1 (2)
O4—N1—C3116.7 (2)C4—C3—N1116.7 (2)
O5—N2—O6123.9 (2)C2—C3—N1121.2 (2)
O5—N2—C5117.8 (2)C5—C4—C3118.4 (2)
O6—N2—C5118.2 (2)C5—C4—H5120.8
C2—O1—H1109.5C3—C4—H5120.8
H7A—O7—H7B95 (3)C4—C5—C6122.0 (2)
C7—N3—H3A103 (2)C4—C5—N2119.0 (2)
C7—N3—H3B138 (4)C6—C5—N2118.9 (2)
H3A—N3—H3B112 (3)C1—C6—C5119.9 (2)
C6—C1—C2119.8 (2)C1—C6—H7120.0
C6—C1—C7120.4 (2)C5—C6—H7120.0
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O7—H7B···O4i0.85 (2)2.03 (2)2.869 (3)168 (3)
O7—H7A···O3ii0.85 (3)2.55 (4)3.301 (3)149 (3)
O7—H7A···O1ii0.85 (3)2.26 (2)2.986 (3)144 (3)
N3—H3A···O7iii0.79 (1)1.84 (1)2.625 (3)175 (3)
O1—H1···O2iv0.822.272.900 (3)134
O1—H1···O20.821.862.575 (2)146
Symmetry codes: (i) x+1/2, y+1/2, z1/2; (ii) x+1, y, z+1/2; (iii) x, y, z+1; (iv) x+1, y, z+3/2.

Experimental details

Crystal data
Chemical formulaC7H5N3O6·H2O
Mr245.16
Crystal system, space groupMonoclinic, C2/c
Temperature (K)273
a, b, c (Å)25.4442 (14), 6.663 (3), 12.486 (2)
β (°) 111.882 (7)
V3)1964.2 (9)
Z8
Radiation typeMo Kα
µ (mm1)0.15
Crystal size (mm)0.24 × 0.15 × 0.14
Data collection
DiffractometerBruker APEXII area-detector
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.965, 0.979
No. of measured, independent and
observed [I > 2σ(I)] reflections
6123, 1891, 979
Rint0.030
(sin θ/λ)max1)0.617
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.047, 0.143, 1.02
No. of reflections1891
No. of parameters171
No. of restraints9
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.22, 0.25

Computer programs: APEX2 (Bruker, 2005), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Siemens, 1996).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O7—H7B···O4i0.851 (18)2.03 (2)2.869 (3)168 (3)
O7—H7A···O3ii0.85 (3)2.55 (4)3.301 (3)149 (3)
O7—H7A···O1ii0.85 (3)2.26 (2)2.986 (3)144 (3)
N3—H3A···O7iii0.787 (13)1.840 (14)2.625 (3)175 (3)
O1—H1···O2iv0.822.272.900 (3)134.2
O1—H1···O20.821.862.575 (2)145.5
Symmetry codes: (i) x+1/2, y+1/2, z1/2; (ii) x+1, y, z+1/2; (iii) x, y, z+1; (iv) x+1, y, z+3/2.
 

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