Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807040779/hk2313sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807040779/hk2313Isup2.hkl |
CCDC reference: 1101500
Key indicators
- Single-crystal X-ray study
- T = 273 K
- Mean (C-C) = 0.005 Å
- R factor = 0.051
- wR factor = 0.180
- Data-to-parameter ratio = 10.5
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT230_ALERT_2_B Hirshfeld Test Diff for O1 - N1 .. 7.21 su PLAT230_ALERT_2_B Hirshfeld Test Diff for N2 - C6 .. 8.98 su PLAT351_ALERT_3_B Long C-H Bond (0.96A) C6 - H2B ... 1.18 Ang. PLAT430_ALERT_2_B Short Inter D...A Contact O2 .. O2 .. 2.60 Ang.
Alert level C PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.97 PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT230_ALERT_2_C Hirshfeld Test Diff for O6 - N4 .. 5.45 su PLAT230_ALERT_2_C Hirshfeld Test Diff for N1 - C1 .. 5.50 su PLAT230_ALERT_2_C Hirshfeld Test Diff for N1 - C5 .. 6.10 su PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.11 PLAT320_ALERT_2_C Check Hybridisation of C6 in Main Residue . ? PLAT322_ALERT_2_C Check Hybridisation of H2B in Main Residue . ? PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 5 PLAT417_ALERT_2_C Short Inter D-H..H-D H2A .. H2A .. 2.13 Ang.
Alert level G PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 6
0 ALERT level A = In general: serious problem 4 ALERT level B = Potentially serious problem 10 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 10 ALERT type 2 Indicator that the structure model may be wrong or deficient 4 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
For general background, see: Desiraju (1995); Desiraju (1997); Braga et al. (1998); Harrop et al. (2003); Qi, Ma et al. (2003); Qi, Qiu et al. (2003); Rauko et al. (2001); Foster et al. (1999); Zhou et al. (1999). For bond-length data, see: Allen et al. (1987).
Crystals of the title compound were synthesized using hydrothermal method in a 23 ml Teflon-lined Parr bomb. Lanthanum (III) nitrate hexahydrate (216.4 mg, 0.5 mmol), 1-hydroxy-2,4-dinitro-6-carboxamidopyridine (229.2 mg, 1 mmol) and distilled water (4 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 colorless solution was decanted from small colorless crystals. These crystals were washed with distilled water followed by ethanol, and allowed to air-dry at room temperature.
H7A, H7B (for OH2) and H2A, H2B (for NH2) were located in difference syntheses and refined isotropically [O—H = 0.85 (2) and 0.85 (3) Å, Uiso(H) = 0.084 (2) and 0.093 (13) Å2; N—H = 0.82 (5) and 0.85 (5) Å, Uiso(H) = 0.11 (4) and 0.12 (6) Å2]. The remaining H atoms were positioned geometrically, with O—H = 0.82 Å (for OH) and C—H = 0.93 Å for aromatic H, and constrained to ride on their parent atoms, with Uiso(H) = xUeq(C,O), where x = 1.2 for aromatic H, and x = 1.5 for OH 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 amido groups are one of the most important classes of biological ligands, the coordination of metal-amido groups complexes are of critical importance in biological systems, organic materials and coordination chemistry. Recently, amido groups with variable coordination modes have been used to construct metal-organic supramolecular structures (Harrop et al., 2003; Qi, Ma et al., 2003; Qi, Qiu et al., 2003; Rauko et al., 2001; Foster et al., 1999; Zhou et al., 1999). We originally attempted to synthesize complexes featuring La metal chains by reaction of the lanthanum(III) ion with 1-hydroxy-2,4-dinitro-6-carboxamidopyridine ligand. Unfortunately, we obtained only the title compound, (I), and we report herein its crystal structure.
In the molecule of (I) (Fig. 1), the bond lengths and angles are within normal ranges (Allen et al., 1987). It contains one 1-hydroxy-2,4-dinitro-6-carbox- amidopyridine molecule and one water molecule.
In the crystal structure, intramolecular N—H···O and O—H···O and intermolecular O—H···N and O—H···O hydrogen bonds (Table 1, Fig. 2) result in the formation of a supramolecular network structure.
For general background, see: Desiraju (1995); Desiraju (1997); Braga et al. (1998); Harrop et al. (2003); Qi, Ma et al. (2003); Qi, Qiu et al. (2003); Rauko et al. (2001); Foster et al. (1999); Zhou et al. (1999). For bond-length data, see: Allen et al. (1987).
Data collection: SMART (Siemens, 1996); 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).
C6H5N4O6·H2O | F(000) = 1016 |
Mr = 247.16 | Dx = 1.798 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -C 2yc | Cell parameters from 1477 reflections |
a = 25.1116 (13) Å | θ = 2.8–26.8° |
b = 6.409 (3) Å | µ = 0.17 mm−1 |
c = 12.228 (2) Å | T = 273 K |
β = 111.914 (3)° | Prism, colorless |
V = 1825.9 (9) Å3 | 0.24 × 0.15 × 0.14 mm |
Z = 8 |
Bruker SMART CCD area-detector diffractometer | 1802 independent reflections |
Radiation source: fine-focus sealed tube | 961 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.030 |
φ and ω scans | θmax = 26.3°, θmin = 3.3° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −31→31 |
Tmin = 0.961, Tmax = 0.976 | k = −7→8 |
5880 measured reflections | l = −14→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)] = 0.051 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.180 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.10 | w = 1/[σ2(Fo2) + (0.0954P)2 + 0.002P] where P = (Fo2 + 2Fc2)/3 |
1802 reflections | (Δ/σ)max < 0.001 |
171 parameters | Δρmax = 0.34 e Å−3 |
6 restraints | Δρmin = −0.35 e Å−3 |
C6H5N4O6·H2O | V = 1825.9 (9) Å3 |
Mr = 247.16 | Z = 8 |
Monoclinic, C2/c | Mo Kα radiation |
a = 25.1116 (13) Å | µ = 0.17 mm−1 |
b = 6.409 (3) Å | T = 273 K |
c = 12.228 (2) Å | 0.24 × 0.15 × 0.14 mm |
β = 111.914 (3)° |
Bruker SMART CCD area-detector diffractometer | 1802 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 961 reflections with I > 2σ(I) |
Tmin = 0.961, Tmax = 0.976 | Rint = 0.030 |
5880 measured reflections |
R[F2 > 2σ(F2)] = 0.051 | 6 restraints |
wR(F2) = 0.180 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.10 | Δρmax = 0.34 e Å−3 |
1802 reflections | Δρmin = −0.35 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 | 0.40223 (9) | 0.2097 (4) | 0.72917 (18) | 0.0690 (7) | |
H1 | 0.4370 | 0.2140 | 0.7463 | 0.104* | |
O2 | 0.50781 (11) | 0.2161 (5) | 0.8613 (2) | 0.0991 (10) | |
O3 | 0.29276 (9) | 0.1316 (4) | 0.63107 (18) | 0.0767 (7) | |
O4 | 0.24231 (9) | 0.3054 (4) | 0.7040 (2) | 0.0754 (7) | |
O5 | 0.30587 (10) | 0.3718 (4) | 1.11209 (19) | 0.0812 (8) | |
O6 | 0.39283 (12) | 0.3006 (4) | 1.2182 (2) | 0.0920 (9) | |
O7 | 0.13173 (10) | 0.2718 (4) | 0.5262 (2) | 0.0702 (7) | |
H7A | 0.1131 (12) | 0.247 (8) | 0.570 (3) | 0.084 (2)* | |
H7B | 0.1644 (6) | 0.270 (5) | 0.582 (2) | 0.093 (13)* | |
N1 | 0.39102 (12) | 0.2308 (4) | 0.8248 (2) | 0.0688 (8) | |
N2 | 0.53304 (9) | 0.2532 (5) | 1.0472 (2) | 0.0500 (6) | |
H2A | 0.516 (3) | 0.155 (6) | 1.006 (5) | 0.11 (4)* | |
H2B | 0.526 (4) | 0.363 (6) | 1.006 (6) | 0.12 (6)* | |
N3 | 0.28695 (11) | 0.2261 (4) | 0.7096 (2) | 0.0568 (7) | |
N4 | 0.35437 (12) | 0.3200 (4) | 1.1256 (2) | 0.0640 (7) | |
C1 | 0.33551 (12) | 0.2440 (4) | 0.8194 (2) | 0.0495 (7) | |
C2 | 0.32299 (13) | 0.2744 (4) | 0.9176 (2) | 0.0517 (7) | |
H2 | 0.2853 | 0.2881 | 0.9124 | 0.062* | |
C3 | 0.36654 (13) | 0.2836 (4) | 1.0208 (3) | 0.0510 (7) | |
C4 | 0.42297 (13) | 0.2684 (4) | 1.0325 (3) | 0.0525 (7) | |
H4 | 0.4522 | 0.2744 | 1.1066 | 0.063* | |
C5 | 0.43531 (11) | 0.2447 (4) | 0.9346 (3) | 0.0518 (7) | |
C6 | 0.49504 (13) | 0.2384 (5) | 0.9435 (3) | 0.0592 (8) |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0383 (12) | 0.1196 (19) | 0.0513 (12) | 0.0013 (11) | 0.0192 (10) | −0.0030 (11) |
O2 | 0.0390 (13) | 0.201 (3) | 0.0591 (15) | 0.0051 (14) | 0.0201 (12) | 0.0031 (15) |
O3 | 0.0529 (13) | 0.114 (2) | 0.0584 (13) | −0.0069 (13) | 0.0150 (11) | −0.0153 (13) |
O4 | 0.0372 (13) | 0.115 (2) | 0.0687 (15) | 0.0086 (11) | 0.0142 (11) | 0.0072 (12) |
O5 | 0.0588 (16) | 0.115 (2) | 0.0808 (16) | 0.0075 (13) | 0.0390 (13) | −0.0070 (14) |
O6 | 0.0717 (18) | 0.151 (2) | 0.0477 (14) | 0.0125 (15) | 0.0155 (13) | −0.0017 (14) |
O7 | 0.0379 (13) | 0.0927 (17) | 0.0711 (15) | −0.0018 (11) | 0.0102 (12) | −0.0045 (12) |
N1 | 0.0546 (18) | 0.088 (2) | 0.0626 (17) | 0.0005 (13) | 0.0209 (15) | 0.0005 (13) |
N2 | 0.0286 (13) | 0.0732 (16) | 0.0403 (13) | −0.0026 (11) | 0.0035 (11) | −0.0013 (11) |
N3 | 0.0377 (15) | 0.0807 (18) | 0.0496 (15) | −0.0028 (12) | 0.0136 (12) | 0.0046 (12) |
N4 | 0.0606 (19) | 0.0761 (18) | 0.0605 (17) | −0.0012 (14) | 0.0286 (16) | −0.0047 (13) |
C1 | 0.0404 (16) | 0.0590 (18) | 0.0479 (16) | 0.0002 (12) | 0.0151 (13) | 0.0037 (12) |
C2 | 0.0430 (17) | 0.0583 (18) | 0.0548 (17) | 0.0012 (12) | 0.0192 (14) | 0.0044 (12) |
C3 | 0.0474 (17) | 0.0606 (18) | 0.0489 (16) | 0.0022 (13) | 0.0224 (14) | 0.0011 (12) |
C4 | 0.0396 (16) | 0.0646 (19) | 0.0492 (17) | −0.0013 (13) | 0.0118 (13) | −0.0011 (12) |
C5 | 0.0356 (16) | 0.0668 (18) | 0.0507 (17) | 0.0003 (12) | 0.0137 (14) | 0.0024 (13) |
C6 | 0.0408 (17) | 0.082 (2) | 0.0548 (19) | 0.0005 (15) | 0.0178 (16) | 0.0057 (16) |
O1—N1 | 1.308 (3) | N2—C6 | 1.275 (4) |
O1—H1 | 0.8200 | N3—C1 | 1.442 (4) |
O2—C6 | 1.172 (4) | N4—C3 | 1.443 (4) |
O3—N3 | 1.189 (3) | C1—C2 | 1.364 (4) |
O4—N3 | 1.209 (3) | C2—C3 | 1.328 (4) |
O5—N4 | 1.213 (3) | C2—H2 | 0.9300 |
O6—N4 | 1.189 (4) | C3—C4 | 1.373 (4) |
O7—H7A | 0.85 (3) | C4—C5 | 1.353 (4) |
O7—H7B | 0.85 (2) | C4—H4 | 0.9300 |
N1—C1 | 1.373 (4) | C5—C6 | 1.463 (4) |
N1—C5 | 1.390 (4) | C6—H2A | 0.92 (6) |
N2—H2A | 0.82 (5) | C6—H2B | 1.17 (7) |
N2—H2B | 0.85 (5) | ||
N1—O1—H1 | 109.5 | N1—C1—N3 | 122.0 (3) |
H7A—O7—H7B | 95 (3) | C3—C2—C1 | 117.7 (3) |
O1—N1—C1 | 121.1 (3) | C3—C2—H2 | 121.2 |
O1—N1—C5 | 120.6 (3) | C1—C2—H2 | 121.2 |
C1—N1—C5 | 118.3 (3) | C2—C3—C4 | 123.2 (3) |
H2A—N2—H2B | 109 (3) | C2—C3—N4 | 118.6 (3) |
H2A—N2—C6 | 46 (4) | C4—C3—N4 | 118.1 (3) |
H2B—N2—C6 | 63 (5) | C5—C4—C3 | 118.9 (3) |
H2B—N2—H2A | 109 (4) | C5—C4—H4 | 120.5 |
C6—N2—H2A | 46 (4) | C3—C4—H4 | 120.5 |
H2A—N2—H2B | 109 (3) | C4—C5—N1 | 119.8 (3) |
C6—N2—H2B | 63 (5) | C4—C5—C6 | 120.3 (3) |
H2A—N2—H2B | 109 (3) | N1—C5—C6 | 119.9 (3) |
O3—N3—O4 | 124.0 (3) | O2—C6—N2 | 121.3 (3) |
O3—N3—C1 | 118.4 (3) | O2—C6—C5 | 122.7 (3) |
O4—N3—C1 | 117.6 (3) | N2—C6—C5 | 116.0 (3) |
O6—N4—O5 | 125.2 (3) | O2—C6—H2A | 113 (5) |
O6—N4—C3 | 117.6 (3) | C5—C6—H2A | 109 (5) |
O5—N4—C3 | 117.3 (3) | O2—C6—H2B | 109 (4) |
C2—C1—N1 | 122.0 (3) | C5—C6—H2B | 116 (5) |
C2—C1—N3 | 116.0 (3) | H2A—C6—H2B | 80 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···O2 | 0.82 | 1.81 | 2.539 (3) | 148 |
N2—H2A···O2 | 0.82 (5) | 1.75 (7) | 2.133 (3) | 106 (5) |
O7—H7B···O4 | 0.85 (2) | 1.98 (2) | 2.824 (3) | 172 (3) |
O1—H1···O2i | 0.82 | 2.24 | 2.863 (3) | 133 |
O7—H7A···N2ii | 0.85 (3) | 1.92 (2) | 2.590 (3) | 135 (3) |
Symmetry codes: (i) −x+1, y, −z+3/2; (ii) x−1/2, −y+1/2, z−1/2. |
Experimental details
Crystal data | |
Chemical formula | C6H5N4O6·H2O |
Mr | 247.16 |
Crystal system, space group | Monoclinic, C2/c |
Temperature (K) | 273 |
a, b, c (Å) | 25.1116 (13), 6.409 (3), 12.228 (2) |
β (°) | 111.914 (3) |
V (Å3) | 1825.9 (9) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.17 |
Crystal size (mm) | 0.24 × 0.15 × 0.14 |
Data collection | |
Diffractometer | Bruker SMART CCD area-detector |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.961, 0.976 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 5880, 1802, 961 |
Rint | 0.030 |
(sin θ/λ)max (Å−1) | 0.624 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.051, 0.180, 1.10 |
No. of reflections | 1802 |
No. of parameters | 171 |
No. of restraints | 6 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.34, −0.35 |
Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Siemens, 1996).
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···O2 | 0.82 | 1.81 | 2.539 (3) | 148 |
N2—H2A···O2 | 0.82 (5) | 1.75 (7) | 2.133 (3) | 106 (5) |
O7—H7B···O4 | 0.85 (2) | 1.98 (2) | 2.824 (3) | 172 (3) |
O1—H1···O2i | 0.82 | 2.24 | 2.863 (3) | 133 |
O7—H7A···N2ii | 0.85 (3) | 1.92 (2) | 2.590 (3) | 135 (3) |
Symmetry codes: (i) −x+1, y, −z+3/2; (ii) x−1/2, −y+1/2, z−1/2. |
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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 amido groups are one of the most important classes of biological ligands, the coordination of metal-amido groups complexes are of critical importance in biological systems, organic materials and coordination chemistry. Recently, amido groups with variable coordination modes have been used to construct metal-organic supramolecular structures (Harrop et al., 2003; Qi, Ma et al., 2003; Qi, Qiu et al., 2003; Rauko et al., 2001; Foster et al., 1999; Zhou et al., 1999). We originally attempted to synthesize complexes featuring La metal chains by reaction of the lanthanum(III) ion with 1-hydroxy-2,4-dinitro-6-carboxamidopyridine ligand. Unfortunately, we obtained only the title compound, (I), and we report herein its crystal structure.
In the molecule of (I) (Fig. 1), the bond lengths and angles are within normal ranges (Allen et al., 1987). It contains one 1-hydroxy-2,4-dinitro-6-carbox- amidopyridine molecule and one water molecule.
In the crystal structure, intramolecular N—H···O and O—H···O and intermolecular O—H···N and O—H···O hydrogen bonds (Table 1, Fig. 2) result in the formation of a supramolecular network structure.