Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807039712/at2370sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807039712/at2370Isup2.hkl |
CCDC reference: 1196852
Key indicators
- Single-crystal X-ray study
- T = 273 K
- Mean (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
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.
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.
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).
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).
C7H5N3O6·H2O | F(000) = 1008 |
Mr = 245.16 | Dx = 1.658 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -C 2yc | Cell parameters from 1511 reflections |
a = 25.4442 (14) Å | θ = 3.1–26.8° |
b = 6.663 (3) Å | µ = 0.15 mm−1 |
c = 12.486 (2) Å | T = 273 K |
β = 111.882 (7)° | Prism, colourless |
V = 1964.2 (9) Å3 | 0.24 × 0.15 × 0.14 mm |
Z = 8 |
Bruker APEXII area-detector diffractometer | 1891 independent reflections |
Radiation source: fine-focus sealed tube | 979 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.030 |
φ and ω scans | θmax = 26.0°, θmin = 3.2° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −31→31 |
Tmin = 0.965, Tmax = 0.979 | k = −8→8 |
6123 measured reflections | l = −15→15 |
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) = 0.143 | H 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 parameters | Δρmax = 0.22 e Å−3 |
9 restraints | Δρmin = −0.25 e Å−3 |
C7H5N3O6·H2O | V = 1964.2 (9) Å3 |
Mr = 245.16 | Z = 8 |
Monoclinic, C2/c | Mo Kα radiation |
a = 25.4442 (14) Å | µ = 0.15 mm−1 |
b = 6.663 (3) Å | T = 273 K |
c = 12.486 (2) Å | 0.24 × 0.15 × 0.14 mm |
β = 111.882 (7)° |
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 = 0.979 | Rint = 0.030 |
6123 measured reflections |
R[F2 > 2σ(F2)] = 0.047 | 9 restraints |
wR(F2) = 0.143 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.02 | Δρmax = 0.22 e Å−3 |
1891 reflections | Δρmin = −0.25 e Å−3 |
171 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
O1 | 0.40219 (7) | 0.2100 (3) | 0.72887 (14) | 0.0733 (6) | |
H1 | 0.4363 | 0.2238 | 0.7445 | 0.110* | |
O2 | 0.50775 (8) | 0.2170 (4) | 0.86062 (17) | 0.1046 (9) | |
O3 | 0.29250 (7) | 0.1318 (3) | 0.63098 (15) | 0.0808 (6) | |
O4 | 0.24220 (7) | 0.3057 (3) | 0.70399 (16) | 0.0788 (6) | |
O5 | 0.30605 (8) | 0.3711 (3) | 1.11219 (16) | 0.0851 (7) | |
O6 | 0.39244 (10) | 0.3009 (4) | 1.21820 (18) | 0.0977 (8) | |
O7 | 0.63147 (8) | 0.2289 (3) | 0.0270 (2) | 0.0747 (6) | |
N1 | 0.28690 (9) | 0.2263 (3) | 0.70936 (18) | 0.0609 (6) | |
N2 | 0.35423 (10) | 0.3195 (3) | 1.12494 (19) | 0.0648 (6) | |
N3 | 0.53256 (8) | 0.2535 (3) | 1.04702 (17) | 0.0518 (5) | |
C1 | 0.43553 (9) | 0.2454 (4) | 0.9348 (2) | 0.0540 (6) | |
C2 | 0.39114 (10) | 0.2307 (4) | 0.8245 (2) | 0.0538 (6) | |
C3 | 0.33530 (10) | 0.2444 (4) | 0.8195 (2) | 0.0521 (6) | |
C4 | 0.32289 (10) | 0.2747 (4) | 0.91675 (19) | 0.0534 (6) | |
H5 | 0.2856 | 0.2884 | 0.9113 | 0.064* | |
C5 | 0.36667 (10) | 0.2842 (4) | 1.0214 (2) | 0.0534 (6) | |
C6 | 0.42273 (10) | 0.2690 (4) | 1.0317 (2) | 0.0549 (6) | |
H7 | 0.4516 | 0.2749 | 1.1042 | 0.066* | |
C7 | 0.49510 (11) | 0.2384 (4) | 0.9443 (2) | 0.0635 (7) | |
H3A | 0.5613 (8) | 0.242 (4) | 1.038 (2) | 0.076 (9)* | |
H7A | 0.6382 (15) | 0.218 (6) | −0.0344 (16) | 0.153 (18)* | |
H7B | 0.6661 (4) | 0.224 (6) | 0.072 (2) | 0.161 (19)* | |
H3B | 0.536 (2) | 0.223 (9) | 1.114 (2) | 0.13 (4)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0388 (10) | 0.1292 (17) | 0.0523 (11) | 0.0006 (10) | 0.0174 (8) | −0.0027 (10) |
O2 | 0.0408 (11) | 0.213 (3) | 0.0625 (14) | 0.0029 (12) | 0.0218 (10) | 0.0000 (13) |
O3 | 0.0550 (11) | 0.1232 (17) | 0.0598 (11) | −0.0076 (11) | 0.0163 (9) | −0.0159 (11) |
O4 | 0.0354 (11) | 0.1272 (17) | 0.0682 (12) | 0.0107 (10) | 0.0127 (9) | 0.0074 (11) |
O5 | 0.0597 (13) | 0.1248 (17) | 0.0806 (13) | 0.0052 (12) | 0.0376 (11) | −0.0096 (12) |
O6 | 0.0746 (16) | 0.159 (2) | 0.0555 (13) | 0.0147 (13) | 0.0196 (12) | −0.0044 (13) |
O7 | 0.0418 (11) | 0.1017 (16) | 0.0737 (13) | 0.0016 (10) | 0.0136 (10) | 0.0045 (11) |
N1 | 0.0395 (13) | 0.0892 (17) | 0.0517 (13) | −0.0033 (11) | 0.0145 (10) | 0.0049 (11) |
N2 | 0.0549 (15) | 0.0851 (17) | 0.0576 (14) | −0.0006 (12) | 0.0246 (13) | −0.0045 (11) |
N3 | 0.0216 (10) | 0.0865 (16) | 0.0402 (12) | −0.0005 (10) | 0.0034 (9) | −0.0003 (9) |
C1 | 0.0365 (14) | 0.0718 (17) | 0.0510 (15) | −0.0003 (11) | 0.0133 (12) | 0.0012 (12) |
C2 | 0.0412 (14) | 0.0726 (17) | 0.0489 (14) | 0.0017 (12) | 0.0183 (12) | 0.0004 (11) |
C3 | 0.0395 (14) | 0.0650 (16) | 0.0476 (14) | −0.0005 (11) | 0.0112 (11) | 0.0044 (11) |
C4 | 0.0404 (14) | 0.0650 (16) | 0.0559 (15) | 0.0011 (11) | 0.0192 (12) | 0.0045 (11) |
C5 | 0.0476 (15) | 0.0633 (16) | 0.0518 (14) | 0.0025 (11) | 0.0212 (12) | 0.0001 (11) |
C6 | 0.0404 (13) | 0.0707 (17) | 0.0493 (14) | −0.0014 (11) | 0.0117 (11) | −0.0008 (11) |
C7 | 0.0450 (15) | 0.087 (2) | 0.0602 (17) | −0.0008 (13) | 0.0212 (14) | 0.0051 (13) |
O1—C2 | 1.331 (3) | N3—H3A | 0.787 (13) |
O2—C7 | 1.211 (3) | N3—H3B | 0.83 (3) |
O3—N1 | 1.216 (3) | C1—C6 | 1.374 (3) |
O4—N1 | 1.233 (3) | C1—C2 | 1.422 (3) |
O5—N2 | 1.225 (3) | C1—C7 | 1.476 (3) |
O6—N2 | 1.214 (3) | C2—C3 | 1.402 (3) |
N1—C3 | 1.470 (3) | C3—C4 | 1.378 (3) |
N2—C5 | 1.461 (3) | C4—C5 | 1.366 (3) |
N3—C7 | 1.285 (3) | C4—H5 | 0.9300 |
O1—H1 | 0.8200 | C5—C6 | 1.387 (3) |
O7—H7A | 0.85 (3) | C6—H7 | 0.9300 |
O7—H7B | 0.851 (18) | ||
O2—C7—N3 | 122.2 (2) | C2—C1—C7 | 119.8 (2) |
O2—C7—C1 | 122.0 (2) | O1—C2—C3 | 121.1 (2) |
N3—C7—C1 | 115.8 (2) | O1—C2—C1 | 121.2 (2) |
O3—N1—O4 | 124.1 (2) | C3—C2—C1 | 117.7 (2) |
O3—N1—C3 | 119.2 (2) | C4—C3—C2 | 122.1 (2) |
O4—N1—C3 | 116.7 (2) | C4—C3—N1 | 116.7 (2) |
O5—N2—O6 | 123.9 (2) | C2—C3—N1 | 121.2 (2) |
O5—N2—C5 | 117.8 (2) | C5—C4—C3 | 118.4 (2) |
O6—N2—C5 | 118.2 (2) | C5—C4—H5 | 120.8 |
C2—O1—H1 | 109.5 | C3—C4—H5 | 120.8 |
H7A—O7—H7B | 95 (3) | C4—C5—C6 | 122.0 (2) |
C7—N3—H3A | 103 (2) | C4—C5—N2 | 119.0 (2) |
C7—N3—H3B | 138 (4) | C6—C5—N2 | 118.9 (2) |
H3A—N3—H3B | 112 (3) | C1—C6—C5 | 119.9 (2) |
C6—C1—C2 | 119.8 (2) | C1—C6—H7 | 120.0 |
C6—C1—C7 | 120.4 (2) | C5—C6—H7 | 120.0 |
D—H···A | D—H | H···A | D···A | D—H···A |
O7—H7B···O4i | 0.85 (2) | 2.03 (2) | 2.869 (3) | 168 (3) |
O7—H7A···O3ii | 0.85 (3) | 2.55 (4) | 3.301 (3) | 149 (3) |
O7—H7A···O1ii | 0.85 (3) | 2.26 (2) | 2.986 (3) | 144 (3) |
N3—H3A···O7iii | 0.79 (1) | 1.84 (1) | 2.625 (3) | 175 (3) |
O1—H1···O2iv | 0.82 | 2.27 | 2.900 (3) | 134 |
O1—H1···O2 | 0.82 | 1.86 | 2.575 (2) | 146 |
Symmetry codes: (i) x+1/2, −y+1/2, z−1/2; (ii) −x+1, y, −z+1/2; (iii) x, y, z+1; (iv) −x+1, y, −z+3/2. |
Experimental details
Crystal data | |
Chemical formula | C7H5N3O6·H2O |
Mr | 245.16 |
Crystal system, space group | Monoclinic, C2/c |
Temperature (K) | 273 |
a, b, c (Å) | 25.4442 (14), 6.663 (3), 12.486 (2) |
β (°) | 111.882 (7) |
V (Å3) | 1964.2 (9) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.15 |
Crystal size (mm) | 0.24 × 0.15 × 0.14 |
Data collection | |
Diffractometer | Bruker APEXII area-detector |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.965, 0.979 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 6123, 1891, 979 |
Rint | 0.030 |
(sin θ/λ)max (Å−1) | 0.617 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.047, 0.143, 1.02 |
No. of reflections | 1891 |
No. of parameters | 171 |
No. of restraints | 9 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.22, −0.25 |
Computer programs: APEX2 (Bruker, 2005), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Siemens, 1996).
D—H···A | D—H | H···A | D···A | D—H···A |
O7—H7B···O4i | 0.851 (18) | 2.03 (2) | 2.869 (3) | 168 (3) |
O7—H7A···O3ii | 0.85 (3) | 2.55 (4) | 3.301 (3) | 149 (3) |
O7—H7A···O1ii | 0.85 (3) | 2.26 (2) | 2.986 (3) | 144 (3) |
N3—H3A···O7iii | 0.787 (13) | 1.840 (14) | 2.625 (3) | 175 (3) |
O1—H1···O2iv | 0.82 | 2.27 | 2.900 (3) | 134.2 |
O1—H1···O2 | 0.82 | 1.86 | 2.575 (2) | 145.5 |
Symmetry codes: (i) x+1/2, −y+1/2, z−1/2; (ii) −x+1, y, −z+1/2; (iii) x, y, z+1; (iv) −x+1, y, −z+3/2. |
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).